(2, 4-dichlorophenoxy) acetic acid analogs
By developing a new compound, the problems of volatile, spray drift and barrel mixing in traditional 2,4-D herbicides have been solved during use, and better herbicidal effect and use safety are achieved.
Patent Information
- Application Number
- CN202380057499.7
- Authority / Receiving Office
- CN · China
- Patent Type
- Applications(China)
- Current Assignee / Owner
- Priority Date
- 2022-08-03
- Filing Date
- 2023-08-03
- Publication Date
- 2025-03-28
AI Technical Summary
During the use of existing 2,4-D herbicides, there are problems such as volatile, spray drift, vapor drift, irritating odor, limited stability, and limited barrel mixing with other pesticide active substances, which affects their use effect and safety.
A novel compound according to formula I, wherein X can be a variety of substituent groups, the formed compound has reduced volatility, improved barrel mixing and better formulation flexibility for substitution of traditional 2,4-D class herbicides.
The new compounds have reduced volatility and spray drift during and after application, reducing damage to sensitive crops, and improving mixing performance with other pesticide active substances, providing greater formulation flexibility and better herbicidal effects.
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Abstract
Description
Technical Field
[0001] Aspects of the present invention include pesticide compositions and agricultural methods, including herbicidal compositions that can be used to control unwanted plants. The herbicides disclosed herein can be used alone in various formulations, or with other agricultural active substances (including other herbicides) to control weeds in various crops.
[0002] The present disclosure includes (2,4-dichlorophenoxy)acetic acid analogs. More specifically, the present disclosure relates to (2,4-dichlorophenoxy)acetic acid analogs, such as esters, amides, aminooxy groups, linkers, and carbon groups. Background Art
[0003] Protecting crops from unwanted vegetation that adversely affects crop growth is a constantly recurring problem in agriculture. To help address this problem, researchers in the field of synthetic chemistry have produced a variety of chemicals and chemical formulations that are effective in controlling the growth of such unwanted plants. Many types of chemical herbicides have been disclosed in the literature, and a large number of chemical herbicides have been used commercially. However, there is still a need for compositions and methods that effectively control unwanted vegetation and exhibit other physicochemical properties that make it easy to formulate and apply under varying field conditions.
[0004] (2,4-Dichlorophenoxy)acetic acid, also known as 2,4-D, is a known herbicide. 2,4-D is commonly used as a herbicide and defoliant. 2,4-D is commonly used as a weed killer in cereal crops, pastures, and orchards.
[0005] However, various forms of 2,4-D may often have unfavorable characteristics such as volatility, spray drift, vapor drift, pungent odor, limited stability, limited tank miscibility with other pesticide actives, and / or limited formulation flexibility.
[0006] Attempts to address the volatility problem, including the preparation of water-soluble salts such as the dimethylamine salt of 2,4-D, have not been entirely satisfactory because upon volatilization of the amine, the herbicide reverts to its original acid form which itself is sufficiently volatile under certain adverse conditions to cause damage to sensitive crops.
[0007] Conventional 2,4-D ester or 2,4-D dimethylamine formulations applied during warm summer months may result in vapor drift due to evaporation of the herbicide from the sprayed surface and subsequent damage to highly susceptible crops such as tomatoes, cotton, soybeans, sunflowers and grapes. This may occur within hours of herbicide application.
[0008] Additionally, conventional 2,4-D ester or conventional 2,4-D dimethylamine formulations may be subject to formulation limitations, such as their ability to be mixed (including tank mixes) with other actives, such as glyphosate.
[0009] Therefore, there is a need for alternative forms of 2,4-D having reduced volatility, reduced spray drift, reduced volatility drift, reduced odor, improved tank miscibility with other pesticide actives, or improved formulation flexibility. Summary of the invention
[0010] Disclosed herein are various compounds according to various details or aspects. Such compounds may include compounds according to Formula I: Where X is: in R 1 are independently hydrogen, C 1 -C 16 Alkyl, C 1 -C 16 Heteroalkyl, C 5 -C 10 Aryl, C 5 -C 10 heteroaryl, alkylcarbonyl, alkoxycarbonyl, aryloxycarbonyl, heteroaryloxycarbonyl, mono- or di-substituted alkylaminocarbonyl, mono- or di-substituted arylaminocarbonyl, mono- or di-substituted heteroarylaminocarbonyl, alkylthiocarbonyl, arylthiocarbonyl, or heteroarylthiocarbonyl; R 2 are independently hydrogen, C 1 -C 16 Alkyl, C 1 -C 16 Heteroalkyl, C 5 -C 10 Aryl, C 5 -C 10 heteroaryl, alkylcarbonyl, alkoxycarbonyl, aryloxycarbonyl, heteroaryloxycarbonyl, mono- or di-substituted alkylaminocarbonyl, mono- or di-substituted arylaminocarbonyl, mono- or di-substituted heteroarylaminocarbonyl, alkylthiocarbonyl, arylthiocarbonyl, heteroarylthiocarbonyl; R 3 are independently hydrogen, C 1 -C 16 Alkyl, C 1 -C 16 Heteroalkyl, C 5 -C 10 Aryl, C 5 -C 10 heteroaryl, alkylcarbonyl, alkoxycarbonyl, aryloxycarbonyl, heteroaryloxycarbonyl, mono- or di-substituted alkylaminocarbonyl, mono- or di-substituted arylaminocarbonyl, mono- or di-substituted heteroarylaminocarbonyl, alkylthiocarbonyl, arylthiocarbonyl, heteroarylthiocarbonyl; R1 and R 2 together to form a substituted double bond, a 3-membered ring, a 4-membered ring, a 5-membered ring, a 6-membered ring, or a 7-membered ring; A is independently O, Si, NR, and S(O) m ;
[0011] A 2 independently O, N, S(O) m , substituted alkyl, heteroalkyl, alkenyl, alkynyl, aryl, heteroaryl, alkylaryl, alkylheteroaryl; Y is independently O, N, S; Z is independently O, N, S(O) m , substituted alkyl, alkenyl, alkynyl, aryl, heteroaryl, alkylcarbonyl, alkoxycarbonyl, aryloxycarbonyl, heteroaryloxycarbonyl, mono- or di-substituted alkylaminocarbonyl, mono- or di-substituted arylaminocarbonyl, mono- or di-substituted heteroarylaminocarbonyl, alkylthiocarbonyl, arylthiocarbonyl, heteroarylthiocarbonyl, -N=R 4 R 5 , R 4 and R 5 are independently substituted amino, alkoxy, alkyl, heteroalkyl, aryl, heteroaryl; n is 1, 2, or 3; and m is 0, 1, or 2; The compound exhibits pesticide activity, provided that the compound is not 2,4-D-isooctyl ester.
[0012] For example, various compounds may include the aforementioned compounds, wherein X is: in R 1 are independently hydrogen, C 1 -C 16 Alkyl, C 1 -C 16 Heteroalkyl, C 5 -C 10 Aryl, C 5 -C 10 heteroaryl, alkylcarbonyl, alkoxycarbonyl, aryloxycarbonyl, heteroaryloxycarbonyl, mono- or di-substituted alkylaminocarbonyl, mono- or di-substituted arylaminocarbonyl, mono- or di-substituted heteroarylaminocarbonyl, alkylthiocarbonyl, arylthiocarbonyl, or heteroarylthiocarbonyl; and R 2 are independently hydrogen, C 1 -C 16 Alkyl, C 1 -C 16 Heteroalkyl, C 5 -C 10Aryl, C 5 -C 10 heteroaryl, alkylcarbonyl, alkoxycarbonyl, aryloxycarbonyl, heteroaryloxycarbonyl, mono- or di-substituted alkylaminocarbonyl, mono- or di-substituted arylaminocarbonyl, mono- or di-substituted heteroarylaminocarbonyl, alkylthiocarbonyl, arylthiocarbonyl, heteroarylthiocarbonyl.
[0013] As yet another example, the various compounds may include compounds according to Formula I, wherein X is: in R 3 are independently hydrogen, C 1 -C 16 Alkyl, C 1 -C 16 Heteroalkyl, C 5 -C 10 Aryl, C 5 -C 10 heteroaryl, alkylcarbonyl, alkoxycarbonyl, aryloxycarbonyl, heteroaryloxycarbonyl, mono- or di-substituted alkylaminocarbonyl, mono- or di-substituted arylaminocarbonyl, mono- or di-substituted heteroarylaminocarbonyl, alkylthiocarbonyl, arylthiocarbonyl, heteroarylthiocarbonyl; A is independently O, Si, NR, and S(O) m , substituted alkyl, alkenyl, alkynyl, aryl, heteroaryl, alkylcarbonyl, alkoxycarbonyl, aryloxycarbonyl, heteroaryloxycarbonyl, mono- or di-substituted alkylaminocarbonyl, mono- or di-substituted arylaminocarbonyl, mono- or di-substituted heteroarylaminocarbonyl, alkylthiocarbonyl, arylthiocarbonyl, heteroarylthiocarbonyl, -N=R 4 R 5 , R 4 and R 5 are independently substituted amino, alkoxy, alkyl, heteroalkyl, aryl, heteroaryl; and m is 0, 1, or 2.
[0014] Additional examples include various compounds that may include compounds according to Formula I, wherein X is: in R 2 are independently hydrogen, C 1 -C 16 Alkyl, C 1 -C 16 Heteroalkyl, C 5 -C 10 Aryl, C 5 -C 10heteroaryl, alkylcarbonyl, alkoxycarbonyl, aryloxycarbonyl, heteroaryloxycarbonyl, mono- or di-substituted alkylaminocarbonyl, mono- or di-substituted arylaminocarbonyl, mono- or di-substituted heteroarylaminocarbonyl, alkylthiocarbonyl, arylthiocarbonyl, heteroarylthiocarbonyl.
[0015] Also included are compounds according to formula I, wherein X is: Among them, A, R 2 , Y, Z and A 2 As mentioned before.
[0016] Additional examples include compounds having the formula: in R 1 are independently hydrogen, C 1 -C 16 Alkyl, C 1 -C 16 Heteroalkyl, C 5 -C 10 Aryl, C 5 -C 10 heteroaryl, alkylcarbonyl, alkoxycarbonyl, aryloxycarbonyl, heteroaryloxycarbonyl, mono- or di-substituted alkylaminocarbonyl, mono- or di-substituted arylaminocarbonyl, mono- or di-substituted heteroarylaminocarbonyl, alkylthiocarbonyl, arylthiocarbonyl, or heteroarylthiocarbonyl; R 2 are independently hydrogen, C1-C16 alkyl, C1-C16 heteroalkyl, C5-C10 aryl, C5-C10 heteroaryl, alkylcarbonyl, alkoxycarbonyl, aryloxycarbonyl, heteroaryloxycarbonyl, mono- or di-substituted alkylaminocarbonyl, mono- or di-substituted arylaminocarbonyl, mono- or di-substituted heteroarylaminocarbonyl, alkylthiocarbonyl, arylthiocarbonyl, heteroarylthiocarbonyl; R 3 are independently hydrogen, C1-C16 alkyl, C1-C16 heteroalkyl, C5-C10 aryl, C5-C10 heteroaryl, alkylcarbonyl, alkoxycarbonyl, aryloxycarbonyl, heteroaryloxycarbonyl, mono- or di-substituted alkylaminocarbonyl, mono- or di-substituted arylaminocarbonyl, mono- or di-substituted heteroarylaminocarbonyl, alkylthiocarbonyl, arylthiocarbonyl, heteroarylthiocarbonyl; R 1 and R 2 together to form a substituted double bond, a 3-membered ring, a 5-membered ring, or a 7-membered ring; A is independently O, Si, NR, and S(O)m;
[0017] A 2 independently O, N, S(O)m , substituted alkyl, heteroalkyl, alkenyl, alkynyl, aryl, heteroaryl, alkylaryl, alkylheteroaryl; Y is independently O, N, S; Z is independently O, N, S(O)m, substituted alkyl, alkenyl, alkynyl, aryl, heteroaryl, alkylcarbonyl, alkoxycarbonyl, aryloxycarbonyl, heteroaryloxycarbonyl, mono- or di-substituted alkylaminocarbonyl, mono- or di-substituted arylaminocarbonyl, mono- or di-substituted heteroarylaminocarbonyl, alkylthiocarbonyl, arylthiocarbonyl, heteroarylthiocarbonyl, -N=R 4 R 5 , R 4 and R 5 are independently substituted amino, alkoxy, alkyl, heteroalkyl, aryl, heteroaryl; n is 1, 2, or 3; and m is 0, 1, or 2
[0018] Various compositions may include any of the aforementioned compounds, wherein the concentration of the active ingredient in the composition is 0.001 to 98 weight percent.
[0019] Such previously described compounds may exhibit various pesticidal activities, such as herbicidal activities.
[0020] Also included herein are methods of controlling undesirable vegetation comprising contacting the vegetation or the locus thereof with a herbicidally effective amount of a compound as previously described or applying to the soil a herbicidally effective amount of a compound as previously described to prevent emergence of the vegetation.
[0021] Methods of controlling undesirable vegetation include methods wherein the disclosed compounds are applied at an application rate of between about 200 grams to about 2,000 grams acid equivalent per hectare (g ae / ha), such as between about 800 g ae / ha to about 1,200 g ae / ha.
[0022] Also included is a method of controlling undesirable vegetation in a crop that has become tolerant or resistant to 2,4-dichlorophenoxyacetic acid, the method comprising contacting the vegetation or its locus with a herbicidally effective amount of a compound according to any of the compounds disclosed herein or applying to the soil a herbicidally effective amount of a compound according to any of the compounds disclosed herein to prevent the emergence of the vegetation. DETAILED DESCRIPTION
[0023] The aspects disclosed below are not intended to be exhaustive or to limit the disclosure to the precise forms disclosed in the following detailed description. Rather, these aspects are selected and described so that others skilled in the art may utilize their teachings.
[0024] While the various concepts of the present disclosure are illustrated and described in detail in the drawings and description herein, the results in the drawings and their description are to be considered illustrative rather than restrictive; it is to be understood that only illustrative aspects have been shown and described and that all changes and modifications that come within the spirit of the present disclosure are desired to be protected. definition
[0025] Unless defined otherwise, scientific and technical terms have the same meaning as commonly understood by one of ordinary skill in the art to which the present disclosure belongs.
[0026] As used herein, unless expressly stated otherwise or clearly implied otherwise, the term "about" refers to a range of plus or minus 10% of a value, for example, about 1.0 encompasses values of 0.9 to 1.1.
[0027] As used herein, unless expressly stated otherwise or otherwise clearly implied, the term "agriculturally active" compound includes any compound that may be beneficial to agriculture, including compounds that, alone or in combination with other compounds, inhibit the growth of plants that are considered undesirable in a given agricultural environment.
[0028] The examples given in the definitions are generally non-exhaustive and should not be construed as limiting the invention disclosed in this document.It is understood that substituents should obey the rules of chemical bonding and steric compatibility constraints with respect to the molecule to which they are attached.
[0029] As used herein, the term "alkane" may be understood to include linear, branched or cyclic substituted or unsubstituted hydrocarbons containing one or more carbon-carbon bonds. Elements and groups that may be used to replace alkanes include, but are not limited to, groups including oxygen, nitrogen, sulfur, halogens or metals, and the connection between the hydrocarbon and the substituent may be via a carbon-carbon bond or through elements other than carbon (including, but not limited to, oxygen, nitrogen and sulfur).
[0030] As used herein, the term "olefin" is understood to refer to a linear, branched or cyclic substituted or unsubstituted hydrocarbon containing at least one carbon-carbon double bond. Elements and groups that can be used to replace olefins include, but are not limited to, groups including oxygen, nitrogen, sulfur, halogens or metals, and the connection between the hydrocarbon and the substituent can be carried out via a carbon-carbon bond or through elements other than carbon (including, but not limited to, oxygen, nitrogen and sulfur).
[0031] As used herein, the term "alkyne" may be understood to include a linear or branched or cyclic substituted or unsubstituted hydrocarbon containing at least one carbon-carbon triple bond. Elements and groups that may be used to replace alkynes include, but are not limited to, groups including oxygen, nitrogen, sulfur, halogens or metals, and the connection between the hydrocarbon and the substituent may be via a carbon-carbon bond or through elements other than carbon (including, but not limited to, oxygen, nitrogen and sulfur).
[0032] As used herein, the term "halogen" may be understood to refer to one or more of the following elements: fluorine, chlorine, bromine and iodine.
[0033] As used herein, the term "aryl" is understood to refer to any group containing at least one aromatic ring. The aromatic ring itself may be substituted or unsubstituted. Elements and groups that can be used to replace the aryl include, but are not limited to, groups including oxygen, nitrogen, sulfur, halogens or metals, and the connection between the hydrocarbon and the substituent may be via a carbon-carbon bond or through elements other than carbon (including, but not limited to, oxygen, nitrogen and sulfur).
[0034] As used herein, the term "heteroaryl" may be understood to include two aromatic rings containing elements other than carbon in the ring structure, including but not limited to oxygen, nitrogen, sulfur, etc. Heteroaryl may include more than one ring structure. Heteroaryl may be substituted or unsubstituted, and the substituents include but are not limited to elements and / or groups including oxygen, nitrogen, sulfur, halogens or metals, and the connection between the hydrocarbon and the substituent may be via a carbon-carbon bond or through elements other than carbon (including but not limited to oxygen, nitrogen and sulfur).
[0035] Exemplary heteroaryl groups include, but are not limited to, benzofuranyl, benzisothiazolyl, benzisoxazolyl, benzoxazolyl, benzothiophenyl, benzothiazolyl, cinnolinyl, furanyl, imidazolyl, indazolyl, indolyl, isoindolyl, isoquinolinyl, isothiazolyl, isoxazolyl, oxadiazolyl, oxazolinyl, oxazolyl, phthalazinyl, pyrazinyl, pyrazolinyl, pyrazolyl, pyridazinyl, pyridinyl, pyrimidinyl, pyrrolyl, quinazolinyl, quinolyl, quinoxalinyl, tetrazolyl, thiazolinyl, thiazolyl, thienyl, triazinyl, and triazolyl.
[0036] Saturated heterocycles are ring structures containing one or more elements other than carbon, including, but not limited to, oxygen, nitrogen, sulfur, etc. Exemplary saturated heterocycles include, but are not limited to, piperazinyl, piperidinyl, morpholinyl, pyrrolidinyl, oxetanyl, tetrahydrofuranyl, tetrahydrothienyl, and tetrahydropyranyl.
[0037] Examples of partially unsaturated heterocycles include, but are not limited to, 1,2,3,4-tetrahydroquinolinyl, 4,5-dihydro-oxazolyl, 4,5-dihydro-1H-pyrazolyl, 4,5-dihydro-isoxazolyl, and 2,3-dihydro-1,3,4-oxadiazolyl.
[0038] As used herein, unless otherwise expressly stated or clearly implied, the term "alkyl" refers to any of the following: linear, branched or cyclic substituted or unsubstituted alkanes, alkenes or alkynes; substituents may include, but are not limited to, halogen, amino, imino, sulfone, sulfoxide, aryl, heteroaryl, ester, ketone, aldehyde, alcohol, acid and / or ester. Unless otherwise expressly stated, any compound that can exist as an isomer, stereoisomer or tautomer can be used in any of its herbicidally active isoforms, configurations or tautomers.
[0039] As used herein, unless expressly stated otherwise or clearly implied otherwise, the term "AMATA" refers to Amaranthus rudis (common waterhemp).
[0040] As used herein, unless expressly stated otherwise or clearly implied otherwise, the term "AMBEL" refers to Ambrosia artemisiifolia (common ragweed).
[0041] As used herein, unless expressly stated otherwise or clearly implied otherwise, the term "ABUTH" refers to Abutilon theophrasti (velvet leaf).
[0042] As used herein, unless expressly stated otherwise or clearly implied otherwise, the term "ERICA" refers to glyphosate resistant Conyza canadensis (L.) (horseweed).
[0043] As used herein, unless expressly stated otherwise or clearly implied otherwise, the term "GLXMA" refers to Glycine max (L.) Merr. (soybean).
[0044] As used herein, unless expressly stated otherwise or clearly implied otherwise, the term "DCM" means dichloromethane.
[0045] As used herein, unless expressly stated otherwise or clearly implied otherwise, the term "EtOAC" refers to ethyl acetate.
[0046] As used herein, unless expressly stated otherwise or clearly implied otherwise, the term "DMF" means dimethylformamide.
[0047] As used herein, unless expressly stated otherwise or clearly implied otherwise, the term “ 2 CO 3 ” refers to potassium carbonate.
[0048] As used herein, unless expressly stated otherwise or expressly implied otherwise, the term "EDC" refers to 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide.
[0049] As used herein, unless expressly stated otherwise or clearly implied otherwise, the term "DMAP" means 4-dimethylaminopyridine.
[0050] As used herein, unless expressly stated otherwise or expressly implied otherwise, the term "DIPEA" refers to N,N-diisopropylethylamine.
[0051] As used herein, unless expressly stated otherwise or clearly implied otherwise, the term “ 3 N" refers to triethylamine.
[0052] As used herein, unless expressly stated otherwise or clearly implied otherwise, the term "HPLC" means high performance liquid chromatography.
[0053] As used herein, unless expressly stated otherwise or clearly implied otherwise, the term "LC-MS" means liquid chromatography-mass spectrometry.
[0054] As used herein, the modifier "about" used in conjunction with a quantity is inclusive of the stated value and has the meaning dictated by the context (e.g., includes at least the degree of error associated with the measurement of a particular quantity). When used in the context of a range, the modifier "about" should also be considered to disclose the range defined by the absolute values of the two endpoints. For example, a range of "about 2 to about 4" also discloses a range of "2 to 4".
[0055] As previously stated, the present disclosure includes (2,4-dichlorophenoxy)acetic acid analogs. More specifically, the present disclosure relates to (2,4-dichlorophenoxy)acetic acid analogs ("2,4-D analogs"), such as esters, amides, aminooxy groups, linkers, and carbon groups.
[0056] Without being limited by any theory, it is believed that various 2,4-D analogs can have improved properties before or during application. Therefore, in the soil or plants, the 2,4-D analogs can be broken down into the active form of 2,4-D acid. Therefore, various 2,4-D analogs disclosed herein can benefit from the aforementioned improved properties and still have acceptable pesticide characteristics.
[0057] Disclosed herein are 2,4-D analogs that can be converted to 2,4-D during or after application. For example, disclosed herein are pesticide compositions having the following formula (I): Wherein X is any group that can be converted to a carboxylic acid during or after application (such as in the soil or in the plant). For example, in some aspects, X can be an aminooxy group, an amide, a carbon chain, an ester, or a linker group.
[0058] For example, in some aspects, X can be: Where R 1 , R 2 , R 3 ,Y,Z,A,A 2 and n are as follows.
[0059] For example, in some aspects, when X is an aminooxy group, the aminooxy group may include some of the following exemplary formulae: in R 1 are independently hydrogen, C 1 -C 16 Alkyl, C 1 -C 16 Heteroalkyl, C 5 -C 10 Aryl, C 5 -C 10 heteroaryl, alkylcarbonyl, alkoxycarbonyl, aryloxycarbonyl, heteroaryloxycarbonyl, mono- or di-substituted alkylaminocarbonyl, mono- or di-substituted arylaminocarbonyl, mono- or di-substituted heteroarylaminocarbonyl, alkylthiocarbonyl, arylthiocarbonyl, or heteroarylthiocarbonyl; R 2 are independently hydrogen, C 1 -C 16 Alkyl, C 1 -C 16 Heteroalkyl, C 5 -C 10 Aryl, C 5 -C 10 heteroaryl, alkylcarbonyl, alkoxycarbonyl, aryloxycarbonyl, heteroaryloxycarbonyl, mono- or di-substituted alkylaminocarbonyl, mono- or di-substituted arylaminocarbonyl, mono- or di-substituted heteroarylaminocarbonyl, alkylthiocarbonyl, arylthiocarbonyl, heteroarylthiocarbonyl; and R 1 and R 2 Together they form a substituted double bond, a 3-membered ring, a 5-membered ring, or a 7-membered ring.
[0060] For example, in some aspects, when X is a linker group, the linker group can connect two or more 2,4-D molecules in one analog, such as in Formula B below:
[0061] Among them A 2 independently O, N, S(O) m , substituted alkyl, heteroalkyl, alkenyl, alkynyl, aryl, heteroaryl, alkylaryl, alkylheteroaryl; Y is independently O, N, S; Z is independently O, N, S(O) m (wherein m=0 or 1 or 2), substituted alkyl, alkenyl, alkynyl, aryl, heteroaryl, alkylcarbonyl, alkoxycarbonyl, aryloxycarbonyl, heteroaryloxycarbonyl, mono- or di-substituted alkylaminocarbonyl, mono- or di-substituted arylaminocarbonyl, mono- or di-substituted heteroarylaminocarbonyl, alkylthiocarbonyl, arylthiocarbonyl, heteroarylthiocarbonyl, -N=R 4 R 5 , R 4 and R 5 are independently substituted amino, alkoxy, alkyl, heteroalkyl, aryl, heteroaryl; n is 1, 2, or 3; and m is 0, 1, or 2.
[0062] Exemplary linker groups may include some of the following exemplary Formula B: Among them A 2 As mentioned before.
[0063] In some aspects, when X is a carbon group, the carbon group may include some of the following exemplary formulas C: Where R 2 As mentioned before.
[0064] In various aspects, when X is an amide group, the amide group may include compounds within the following exemplary formula D: Where R 1 and R 2 As mentioned before.
[0065] Some exemplary compounds of Formula D within the present disclosure include the following exemplary compounds: Among them, A, R 1 , R 2 and R 3 As mentioned before.
[0066] In some aspects, when X forms an ester, the ester group may include some of the following exemplary formulas E: Where R 2 As mentioned before.
[0067] As used herein, herbicide means a compound, such as an active ingredient, that kills, controls or otherwise adversely affects the survival, growth and / or reproduction of plants.
[0068] As used herein, an herbicidally effective amount or vegetation controlling amount is that amount of active ingredient which causes an adverse effect on vegetation (e.g., causes deviation from natural development, kills, achieves regulation, causes dehydration, causes delayed development, etc.).
[0069] As used herein, controlling undesirable vegetation refers to preventing, reducing, killing or otherwise adversely changing the growth of plants and vegetation. This paper describes the method of controlling undesirable vegetation by applying some herbicide combinations or compositions. Application methods include but are not limited to application methods via hand, backpack, machine, tractor or high altitude (aircraft and helicopter), application (for example, to application in an area adjacent to vegetation) to vegetation or its location and before emergence, after emergence, foliage (broadcasting, directional, banded, spot-seeding, mechanical, top or rescue) application and in water (vegetation that emerges and floods, broadcasting, spot-seeding, mechanical, water-injected, particle broadcasting, particle spot-seeding, shake bottle or air flow spray) application.
[0070] As used herein, plants and vegetation include, but are not limited to, germinating seeds, emerging seedlings, plants emerging from vegetative propagules, immature vegetation, and established vegetation.
[0071] As used herein, agriculturally acceptable salts and esters refer to salts and esters that exhibit herbicidal activity, or are converted to the reference herbicide in plants, water, or soil, or are convertible to the reference herbicide in plants, water, or soil. Exemplary agriculturally acceptable esters are, for example, those that are hydrolyzed, oxidized, metabolized, or otherwise converted to the corresponding carboxylic acid in plants, water, or soil, or that are hydrolyzed, oxidized, metabolized, or otherwise converted to the corresponding carboxylic acid, which, depending on pH, may be in dissociated or undissociated form.
[0072] Exemplary salts include those derived from alkali metals or alkaline earth metals and those derived from ammonia and amines. Exemplary cations include sodium, potassium, magnesium and the ammonium cation of the formula:
[0073] When these compounds are directly applied to the location of plants or plants at any stage of growth, they show herbicidal activity. The observed effect depends on the plant species to be controlled, the growth stage of the plant, the application parameters of dilution and spray droplet size, the particle size of the solid component, the environmental conditions during use, the specific compound used, the specific adjuvant and carrier used, soil type, etc., and the amount of the applied chemical. These factors and other factors can be adjusted to promote non-selective or selective herbicidal effects. In some aspects, the composition as described herein is applied to flooded rice or water bodies (such as ponds, lakes and streams) as post-emergence application, pre-emergence application, or in water, applied to relatively immature undesirable vegetation to achieve maximum control of weeds.
[0074] In some aspects, the compositions and methods provided herein are used to control weeds in crops including, but not limited to, direct-seeded, hydroseeded and transplanted rice, cereals, wheat, barley, oats, rye, sorghum, corn / maize, sugarcane, sunflower, rapeseed, canola, sugar beet, soybean, cotton, pineapple, pasture, grassland, rangeland, fallow land, turf, tree and vine orchards, water bodies, planted crops, vegetables, industrial vegetation management (IVM) and roadways (ROW).
[0075] About these methods, in some aspects, these methods include contacting undesirable vegetation or its location or being applied to soil or water to prevent the emergence or growth of vegetation or compositions described herein. In some aspects, the composition is applied with an application rate sufficient to control, inhibit or promote at least one plant growth. In some aspects, based on the total amount of active ingredient in the composition, the compound is applied with at least one of the following ranges: about 200 grams to about 2,000 grams of acid equivalents / hectare (g ae / ha); in some aspects, the composition is applied with an application rate of about 400 grams to about 1,500 grams of g ae / ha; in some aspects, the composition is applied with an application rate of about 560 grams to about 1,200 grams of g ae / ha; the composition is applied with an application rate of about 800 grams to about 1,120 grams of g ae / h; in some aspects, these methods include contacting undesirable vegetation or its location or being applied to soil or water to prevent the emergence or growth of vegetation.
[0076] The compositions and methods provided herein are used to control undesirable vegetation. Undesirable vegetation includes, but is not limited to, undesirable vegetation that occurs in rice, cereals, wheat, barley, oats, rye, pastures, grasslands, pastures, fallow land, row crops (e.g., corn / maize, sugarcane, sunflower, rape, canola, sugar beet, soybean, cotton), turf, trees and liana orchards, planted crops, vegetables, ornamental species, aquatic or non-crop environments (e.g., public access roads, industrial vegetation management).
[0077] In some aspects, the method provided herein is used to control undesirable vegetation in rice. In some aspects, undesirable vegetation is Brachiaria platyphylla (Groseb.) Nash or Urochloa platyphylla (Nash) RD Webster) (broadleaf signalgrass, BRAPP), Digitaria sanguinalis (L.) Scop.) (large crabgrass, DIGSA), Echinochloa species (ECHSS), Echinochloa crus-galli (L.) P.Beauv.) (barnyardgrass, ECHCG), Echinochloa crus-pavonis (Kunth) Schult.) (gulf cockspur, ECHCV), Echinochloa bald (Echinochloa colonum (L.) LINK) (junglerice, ECHCO), Echinochloa oryzoides (Ard.) Fritsch (early watergrass, ECHOR), Echinochloa oryzicola (Vasinger) Vasinger (late watergrass, ECHPH), Echinochloa phyllopogon (Stapf) Koso-Pol. (rice barnyardgrass, ECHPH), Echinochloa polystachya (Kunth) Hitchc. (creeping river grass, ECHPO), Ischaemum rugosum Salisb. (saramollagrass, ISCRU), Leptochloa chinensis (Leptochloa phyllopogon (Stapf) Koso-Pol.) (rice barnyardgrass, ECHPH), chinensis (L.) Nees) (Chinese sprangletop, LEFCH), Leptochloa fascicularis (Lam.) Gray (bearded sprangletop, LEFFA), Leptochloa panicoides (Presl.) Hitchc.)(Amazon sprangletop, LEFPA), Oryza species (red and weedy rice, ORYSS), Panicum dichotomiflorum (L.) Michx. (fall panicum, PANDI), Paspalum dilatatum Poir. (dallisgrass, PASDI), Rottboellia cochinchinensis (Lour.) WD Clayton (itchgrass, ROOEX), Cyperus species (CYPSS), Cyperus difformis L. (smallflower flatsedge, CYPDI), Cyperus dubius Rottb. (MAPDU), Cyperus esculentus L. (yellow nutsedge (CYPES), Cyperus iria L. (rice flatsedge, CYPIR), Cyperus rotundus L. (purple nutsedge, CYPRO), Cyperus serotinus Rottb. / CBClarke (tidalmarsh flatsedge, CYPSE), Eleocharis species (ELOSS), Fimbristylis miliacea (L.) Vahl (globe fringerush, FIMMI), Schoenoplectus species (SCPSS), Schoenoplectus juncoides Roxb. (Japanese bulrush, SCPJU), Bolboschoenus maritimus (L.) Palla or Schoenoplectus maritimus L.Lye) (seaclubbrush, SCPMA), Schoenoplectus mucronatus L.)(ricefield bulrush, SCPMU), Aeschynomene species (joint vetch, AESSS), Alternanthera philoxeroides (Mart.) Griseb. (alligatorweed, ALRPH), Alisma plantago-aquatica L. (common water plantain, ALSPA), Amaranthus species (pigweeds and amaranths, AMASS), Ammannia coccinea Rottb. (redstem, AMMCO), Commelina benghalensis L. (Benghal dayflower, COMBE), Eclipta alba (L.) Hassk. (American false chrysanthemum, ALSPA), daisy, ECLAL), Heterantheralimosa (SW.) Willd. / Vahl (duck salad, HETLI), Heterantherareniformis R.&P. (roundleaf mudplantain, HETRE), Ipomoea species (morning glories, IPOSS), Ipomoea hederacea (L.) Jacq. (ivy leaf morningglory, IPOHE), Lindernia dubia (L.) Pennell (low false pimpernel, LIDDU), Ludwigia species (LUDSS), Ludwigia linifolia Poir. (southeastern primrose-willow, LUDLI), Ludwigia octovalvis (Jacq.) Raven)(Longfruited primrose-willow, LUDOC), Monochoria korsakowii Regel & Maack)(monochoria, MOOKA), Monochoria vaginalis(Burm.F.)C.Presl ex Kuhth)(MOOVA), Murdannia nudiflora(L.)Brenan)(doveweed, MUDNU), Polygonum pensylvanicum L.)(Pennsylvaniasmartweed, POLPY), Polygonum persicaria L.)(ladysthumb, POLPE), Polygonum hydropiperoides Michx.(POLHP, mildew smartweed), Rotalaindica (Willd.) Koehne (Indian toothcup, ROTIN), Sagittaria species (arrowhead, SAGSS), Sesbania exaltata (Raf.) Cory / Rydb. Ex Hill (hemp sesbania, SEBEX), or Sphenoclea zeylanica Gaertn. (gooseweed, SPDZE). .
[0078] In some aspects, the methods provided herein are used to control undesirable vegetation in cereals. In some aspects, the undesirable vegetation is Alopecurus myosuroides Huds. (blackgrass, ALOMY), Apera spica-venti (L.) Beauv. (windgrass, APESV), Avena fatua L. (wild oat, AVEFA), Bromus tectorum L. (downy brome, BROTE), Lolium multiflorum Lam. (Italian ryegrass, LOLMU), Phalaris minor Retz. (littleseed canarygrass, PHAMI), Poa annua L. (annual bluegrass, POANN), Setaria officinalis L. (setaria repens L.) (downy brome, BROTE), Lolium multiflorum Lam. (Italian ryegrass, LOLMU), Phalaris minor Retz. (littleseed canarygrass, PHAMI), Poa annua L. (annual bluegrass, POANN), pumila (Poir.) Roemer & J.A. Schultes) (yellow foxtail, SETLU), Setaria viridis (L.) Beauv. (green foxtail, SETVI), Amaranthus retroflexus L. (redroot pigweed, AMARE), Brassica species (BRSSS), Chenopodium album L. (common lambsquarters, CHEAL), Cirsium arvense (L.) Scop. (Canada thistle, CIRAR), Galium aparine L. (catchweed bedstraw, GALAP), Kochia scoparia (L.) Schrad. (KCHSC), Lamium purpureum L.) (purple dead nettle, LAMPU), Matricaria recutita L.) (wild chamomile, MATCH), Matricaria matricarioides (Less.)Porter)(pineappleweed, MATMT), Papaver rhoeas L.(common poppy, PAPRH), Polygonum convolvulus L.(wild buckwheat, POLCO), Salsola tragus L.(Russian thistle, SASKR), Sinapis species (SINSS), Sinapis arvensis L.(wild mustard, SINAR), Stellaria media(L.)Vill.(common chickweed, STEME), Veronica persica Poir.(Persian speedwell, VERPE), Viola arvensis Murr.(field violet, violet, VIOAR), or Viola tricolor L. (wild violet, VIOTR). .
[0079] In some aspects, the methods provided herein are used to control undesirable vegetation in pasture and rangeland, fallow land, IVM, and ROW. In some aspects, the undesirable vegetation is Ambrosia artemisiifolia L. (common ragweed, AMBEL), Cassia obtusifolia (sickle pod, CASOB), Centaurea maculosa auct. non Lam. (spotted knapweed, CENMA), Cirsium arvense (L.) Scop. (Canada thistle, CIRAR), Convolvulus arvensis L. (field bindweed, CONAR), Daucus carota L. (wild carrot, DAUCA), Euphorbia esula L. (leafy spurge, EPHES), Lactuca serriola L. / Torn. (prickly lettuce, LACSE), Plantago asiatica (Plantago serrata L.) (wild carrot, DAUCA), Euphorbia esula L. (leafy spurge, EPHES), Lactuca serriola L. / Torn. (prickly lettuce, LACSE), lanceolata L. (buckhorn plantain, PLALA), Rumex obtusifolius L. (broadleaf dock, RUMOB), Sida spinosa L. (prickly sida, SIDSP), Sinapis arvensis L. (wild mustard, SINAR), Sonchus arvensis L. (perennial sowthistle, SONAR), Solidago species (goldenrod, SOOSS), Taraxacum officinale GHWeber ex Wiggers (dandelion, TAROF), Trifolium repens L. (white clover, clover, TRFRE), or Urtica dioica L. (common nettle, URTDI).
[0080] In some aspects, the methods provided herein are used to control undesirable vegetation found in row crops, tree and vine crops, and perennial crops. In certain aspects, the undesirable vegetation is Alopecurus myosuroides Huds. (black grass, ALOMY), Avena fatua L. (wild oats, AVEFA), Brachiaria decumbens Stapf. or Urochloa decumbens (Stapf) RD Webster (Surinam grass, BRADC), Brachiaria brizantha (Hochst. ex A. Rich.) Stapf. or Urochloa brizantha (Hochst. ex A. Rich.) RD) (beard grass, BRABR), Brachiaria platyphylla (Groseb.) Nash or Urochloa platyphylla (Nash) RD Webster (broadleaf signal grass, BRAPP), Brachiaria plantaginea (Brachiaria plantaginea (Link) Hitchc. or Urochloa plantaginea (Link) RDWebster) (alexandergrass, BRAPL), Cenchrus echinatus L. (southern sandbur, CENEC), Digitaria horizontalis Willd. (Jamaican crabgrass, DIGHO), Digitaria insularis (L.) Mez ex Ekman (sourgrass, TRCIN), Digitaria sanguinalis (L.) Scop. (big crabgrass, DIGSA), Echinochloa crus-galli (L.) P. Beauv. (barnyardgrass, ECHCG), Echinochloa colonum (L.) Link (barnyardgrass, ECHCO), Eleusine indica (L.) Gaertn.) (goosegrass, ELEIN), Lolium multiflorum Lam.)(Italian ryegrass, LOLMU), Panicum dichotomiflorum Michx. (autumn millet, PANDI), Panicum miliaceum L. (wild-proso millet, PANMI), Setaria faberi Herrm. (giant foxtail, SETFA), Setaria viridis (L.) Beauv. (green foxtail, SETVI), Sorghum halepense (L.) Pers. (Johnsongrass, SORHA), Sorghum bicolor (L.) Moench ssp. Arundinaceum (shattercane, SORVU), Cyperus esculentus L. (yellow nutsedge, CYPES), Cyperus rotundus L.) (purple sedge, CYPRO), Abutilon theophrasti Medik. (velvetleaf, ABUTH), Amaranthus species (quinoa and amaranth, AMASS), Ambrosia artemisiifolia L. (common ragweed, AMBEL), Ambrosia psilostachya DC. (western ragweed, AMBPS), Ambrosia trifida L. (giant ragweed, AMBTR), Anoda cristata (L.) Schlecht. (spurred anoda, ANVCR), Asclepias syriaca L. (common milkweed, ASCSY), Bidens pilosa L. (hairy beggarticks, BIDPI), Borreria species (BOISS), Borreria alata (Aubl.) DC. or Spermacocealata Aubl.) (broadleaf buttonweed, BOILF), Spermacoselatifolia (broadleaf buttonweed, BOILF), Chenopodium album L. (common gray vegetable, CHEAL), Cirsium arvense (L.) Scop. (Canada thistle, CIRAR), Commelina benghalensis L. (tropical spiderwort, COMBE), Datura stramonium L. (DATST), Daucus carota L. (wild carrot, DAUCA), Euphorbia heterophylla L. (wild poinsettia, EPHHL), Euphorbia hirta L. or Chamaesyce hirta (L.) Millsp. (garden spurge (garden euphorbia spurge, EPHHI), Euphorbia dentata Michx. (toothed spurge, EPHDE), Erigeron bonariensis L. or Conyza bonariensis (L.) Cronq. (hairy fleabane, ERIBO), Erigeron canadensis L. (Canadian fleabane, ERICA), Conyza sumatrensis (Retz.) EHWalker (tall fleabane, ERIFL), Helianthus annuus L. (common sunflower, HELAN), Jacquemontia tamnifolia (L.) Griseb. (small morning glory, IAQTA), Ipomoea hederacea (L.) Jacq.) (IPOHE), Ipomoea lacunosa L. (IPOLA), Lactuca serriola L. / Torn. (LACSE), Portulaca oleracea L.) (common purslane, POROL), Richardia species (pusley, RCHSS), Sida species (Sida, SIDSS), Sida spinosa L. (spiny yellow flower, SIDSP), Sinapis arvensis L. (wild mustard, SINAR), Solanum ptychanthum Dunal (eastern black nightshade, SOLPT), Tridax procumbens L. (coat buttons, TRQPR), or Xanthium strumarium L. (common cocklebur, XANST). .
[0081] In some respects, the method provided herein is used to control undesirable vegetation in turf. In some respects, undesirable vegetation is daisy (Bellis perennis L.) (English daisy (English daisy), BELPE), oil sedge (Cyperus esculentus L.) (yellow sedge, CYPES), sedge (Cyperus) species (CYPSS), crabgrass (Digitaria sanguinalis (L.) Scop.) (big crabgrass, DIGSA), Virginia button grass (Diodiavirginiana L.) (Virginia buttonweed (Virginia buttonweed), DIQVI), Euphorbia (Euphorbia) species (Euphorbia, EPHSS), Glechoma hederacea L. (ground ivy, GLEHE), Hydrocotyle umbellata (Hydrocotyle umbellata) (ground ivy, GLEHE), L.) (dollarweed, HYDUM), Kyllinga species (kyllinga, KYLSS), Lamium amplexicaule L. (henbit, LAMAM), Murdannia nudiflora (L.) Brenan (doveweed, MUDNU), Oxalis species (woodsorrel, OXASS), Plantago major L. (broadleaf plantain, PLAMA), Plantago lanceolata L. (buckhorn / narrowleaf plantain, PLALA), Phyllanthus urinaria L. (chamberbitter, PYLTE), Rumexobtusifolius L. (broadleaf dock, RUMOB), Stachys floridanaShuttlew. (Florida betony, STAFL), Stellaria media (L.) Vill. (Common chickweed, STEME), Taraxacum officinale GHWeber ex Wiggers (Dandelion, TAROF), Trifolium repens L.) (white clover, TRFRE), or Viola species (wild violet, VIOSS). .
[0082] In some respects, provided herein are compositions and methods for controlling undesirable vegetation, including grass weeds, broadleaf weeds and sedge weeds. In some respects, provided herein are compositions and methods for controlling undesirable vegetation, including but not limited to Alopecurus, Avena, Centaurea, Cyperus, Digitaria, Echinochloa, Ipomoea, Leptochloa and Sonchus.
[0083] In some aspects, the combination of compounds of formula (I) or formulations thereof can be used to control Abutilontheophrasti Medik. (hairy leaf, ABUTH), Amaranthus rudis Sauer (common waterhemp, AMATA), Chenopodium album L. (common gray grass, CHEAL), Polygonum convolvulus L. (wild buckwheat, POLCO) and Sinapis arvensis L. (wild mustard, SINAR).
[0084] Compounds of formula (I) or agriculturally acceptable formulations thereof can be used to control herbicide resistant or tolerant weeds. Exemplary resistant or tolerant weeds include, but are not limited to, acetolactate synthase (ALS) or acetohydroxyacid synthase (AHAS) inhibitors (e.g., imidazolinones, sulfonylureas, pyrimidinylthiobenzoates, triazolopyrimidines, and sulfonylaminocarbonyltriazolinones), photosystem II inhibitors (e.g., phenylcarbamates, pyridazinones, triazinones, triazinones, uracils, amides, ureas, benzothiadiazinones, nitrites, phenylpyridazines), acetyl-CoA carboxylase (ACCase) inhibitors (e.g., aryloxyphenoxypropionates, cyclohexanediones, phenylpyrazoline), synthetic auxins (e.g., benzoic acid, phenoxycarboxylic acid, pyridinecarboxylic acid, quinolinecarboxylic acid), auxin transport inhibitors (e.g., o-benzamide formate, semicarbazone), photosystem I inhibitors (e.g., bipyridinium), 5-enolpyruvylshikimate-3-phosphate (EPSP) synthase inhibitors (e.g., glyphosate), glutamine synthase inhibitors (e.g., glufosinate, bialaphos), microtubule assembly inhibitors (e.g., benzamide, benzoic acid, dinitroaniline, aminophosphorylates, pyridine), mitotic inhibitors (e.g., carbamates), very long chain fatty acids (VLCFAs ) inhibitors (e.g., acetamide, chloroacetamide, oxyacetamide, tetrazolinone), fatty acid and lipid synthesis inhibitors (e.g., phosphorodithioates, thiocarbamates, benzofurans, chlorocarbonates), protoporphyrinogen oxidase (PPO) inhibitors (e.g., diphenyl ether, N-phenylphthalimide, oxadiazole, oxazolidinedione, phenylpyrazole, pyrimidinedione, thiadiazole, triazolinone), carotenoid biosynthesis inhibitors (e.g., isocyanate, chlorfenapyr, fenpropimorph), phytoene dehydrogenase (PDS) inhibitors (e.g., amides, anilide dextrins ( anilidex), furanones, phenoxybutyramides, pyridiazinone, pyridines), 4-hydroxyphenylpyruvate dioxygenase (HPPD) inhibitors (e.g., callistemones, isoxazoles, pyrazoles, triketides), cellulose biosynthesis inhibitors (e.g., nitriles, benzamides, quinclorac, triazolocarboxamides), herbicides with multiple modes of action such as quinclorac and unclassified herbicides such as arylaminopropionic acids, diquat, chloranil or organoarsenic resistant or tolerant biotypes. Exemplary resistant or tolerant weeds include, but are not limited to, biotypes resistant or tolerant to multiple herbicides, biotypes resistant or tolerant to multiple chemical classes, biotypes resistant or tolerant to multiple herbicide modes of action, and biotypes with multiple resistance or tolerance mechanisms (e.g., target site resistance or metabolic resistance).
[0085] About processing crop fields to reduce or eliminate the method for unwanted plant growth, these methods can include making undesirable vegetation or its location contact or be applied to soil or water to prevent the emergence or growth of vegetation or composition as herein described. In some respects, based on the total amount of active ingredient in the composition, the composition is applied with an application rate of about 1 gram of acid equivalent / hectare (g ae / ha) to about 400 grams of active ingredient / hectare (g ae / ha). In some aspects, based on the total amount of active ingredient in the composition, the composition is applied with an application rate of about 4 grams of acid equivalent / hectare (g ae / ha) to about 400g ae / ha.
[0086] About these methods, in some aspects, these methods include contacting undesirable vegetation or its location or being applied to soil or water to prevent the emergence or growth of vegetation or compositions described herein. In some aspects, the composition is applied with an application rate sufficient to control, inhibit or promote at least one plant growth. In some aspects, based on the total amount of active ingredient in the composition, the compound is applied with at least one of the following ranges: about 1 gram to about 1,000 grams of acid equivalents / hectare (g ae / ha); in some aspects, the composition is applied with an application rate between about 1 gram to about 500 grams of g ae / ha; in some aspects, the composition is applied with an application rate between about 1 gram to about 250 grams of g ae / ha; the composition is applied with an application rate between about 1 gram to about 140 grams of g ae / h; in some aspects, the composition is applied with an application rate between about 1 gram to about 70 grams of g ae / ha. In some aspects, these methods include contacting undesirable vegetation or its location or being applied to soil or water to prevent the emergence or growth of vegetation.
[0087] In some aspects, the concentration of active ingredient in the composition described herein is about 0.0005 to 98 weight percent. In some aspects, the concentration is about 0.0006 to 90 weight percent. In the composition designed to be used as a concentrate, in some aspects, the active ingredient is present at a concentration of about 0.1 to 98 weight percent and about 0.5 to 90 weight percent in some aspects. In some aspects, such compositions are diluted with an inert carrier such as water before application. The diluted composition usually applied to weeds or weed locations contains about 0.0006 to 3.0 weight percent active ingredients and contains about 0.01 to 1.0 weight percent active ingredients in some aspects.
[0088] The compositions of the present invention can be applied to weeds or their loci by almost any conventional application method, including but not limited to using air dusters, sprayers and granule applicators. In some cases, these compounds and their formulations can be added to irrigation water or paddy water, which is then used to treat plants, soil and other surfaces.
[0089] The described aspects and the following examples are for illustrative purposes and are not intended to limit the scope of the claims. Other modifications, uses, or combinations of the compositions described herein will be apparent to those of ordinary skill in the art without departing from the spirit and scope of the claimed subject matter.
[0090] Exemplary molecules in the aforementioned formula according to various aspects may include any one of the compounds exemplified in Table 1 below. Table 1: Pesticide compounds Examples
[0091] The following exemplary organic synthesis pathways can be used to produce some of the various compounds disclosed herein. Although these exemplary organic synthesis pathways will be understood by those of ordinary skill, it is within the knowledge of those skilled in the art (with the benefit of this disclosure) to utilize these pathways and to perform other organic synthesis pathways (whether or not explicitly described herein). Therefore, this disclosure will not be regarded as a limitation to those of ordinary skill, and after reading this specification, it may be apparent to those skilled in the relevant art how to synthesize the various compounds described herein with alternative organic synthesis pathways.
[0092] In addition, many of the inputs to the synthetic pathways are commercially available. Thus, in some instances, selected raw materials above the intermediates include a CAS number, for example, when commercially available. Solution 1 Example S1-1 2-(2,4-dichlorophenoxy)benzyl acetate
[0093] (Bromomethyl)benzene (0.46 g, 2.71 mmol) in DMF (5 mL) was added to K at room temperature. 2 CO 3 In a mixture in DMF (10 mL), and stirred for 10 min. The mixture was cooled to 0 ° C, then 2,4-dichlorophenoxyacetic acid (0.5 g, 2.26 mmol) was added under argon atmosphere and stirred at room temperature for 16 h. After the reaction was complete, water (50 mL) was added and the mixture was extracted with EtOAc (2x100 mL). The combined organic extracts were washed with brine and purified by Na 2 SO 4 Drying, filtering and concentration in vacuo gave the crude product. Purification by flash column chromatography (silica gel; gradient elution 0-30% EtOAc:hexanes) gave the title compound E4 (0.33 g, 47%) as an off-white solid. 1 H NMR (400 MHz, CDCl 3 ): δ7.38(d,J=2.5Hz,1H),7.29(m,5H),7.11(dd,J=8.8,2.5Hz,1H),6.73(d,J=8.8Hz,1H),5.23(s,2H),4.72(s,2H). LCMS:m / z=333.0.1[M+Na] + . Solution 2 Example S2-1 - Compound 3: 2-(2,4-dichlorophenoxy)acetyl chloride
[0094] 2,4-Dichlorophenoxyacetic acid (100 g, 0.452 mol) was dissolved in SOCl 2 (340 mL) and the reaction mixture was heated at 80 °C for 4 h. The reaction was monitored for completion by HPLC. After the reaction was complete, excess SOCl was removed in vacuo 2 , affording the title compound 3 (98.5 g, 90%) as a light yellow oil. 1 H NMR (400 MHz, CDCl 3 ): δ7.42 (d, J = 2.5 Hz, 1H), 7.20 (dd, J = 8.8, 2.5 Hz, 1H), 6.82 (d, J = 8.8 Hz, 1H), 4.99 (s, 2H). LCMS: No molecular ion was detected. Example S2-2 (2-(2,4-dichlorophenoxy)acetoxy)methyl benzoate
[0095] To a solution of 2,4-dichlorophenoxyacetic acid (1 g, 4.52 mmol) in toluene (25 mL) was added Ag at room temperature. 2 CO 3 In the mixture of 4-nitro-1-nitro-2-yl pyridine ... 1 H NMR (400MHz, DMSO-d6): δ7.95(m,2H),7.68(m,1H),7.53(m,3H),7.29(dd,J=8.9,2.6Hz,1H),7.14(d,J=8.9Hz,1H),6.05(s,2H),5.08(s,2H). LCMS: m / z=376.97[M+Na] + . Example S2-3 Methylene bis(2-(2,4-dichlorophenoxy)acetate)
[0096] To a solution of 2,4-dichlorophenoxyacetic acid (0.44 g, 2 mmol) in 1:1 DMSO:DCM (14 mL) was added K 2 CO 3 (0.28 g, 4 mmol), and the mixture was stirred at room temperature for 15 min. The reaction mixture was then sealed and heated to 130 ° C for 5 h. After the reaction was completed, water (50 mL) was added; the obtained solid was collected by suction filtration and dried by suction to give the title compound B15 (1 g, 33%) as a white solid. 1 H NMR (400MHz, DMSO-d6): δ7.62 (dd, J = 2.6, 1.2 Hz, 1H), 7.35 (dd, J = 8.8, 2.6 Hz, 1H), 7.14 (d, J = 9.0 Hz, 1H), 5.86 (s, 1H), 5.04 (s, 2H). LCMS: m / z=476.89[M+Na] + . Example S2-4 1,4-phenylenebis(methylene)bis(2-(2,4-dichlorophenoxy)acetate)
[0097] To a solution of 2,4-dichlorophenoxyacetic acid (1 g, 4.52 mmol) in DMF (7 mL) was added K2 CO 3 (0.9 g, 6.78 mmol), and the mixture was stirred at room temperature for 10 min. The mixture was cooled to 0 ° C, and then a, a'-dibromo-p-xylene (0.6 g, 2.26 mmol) was added under argon atmosphere and stirred at room temperature for 16 h. After the reaction was completed, water (100 mL) was added and the mixture was extracted with EtOAc (2x100 mL). The combined organic extracts were washed with brine and purified by Na 2 SO 4 Drying, filtering and concentration in vacuo gave the crude product. Purification by flash column chromatography (silica gel; gradient elution 0-50% EtOAc:hexanes) gave the title compound Bl (0.5 g, 42%) as a white solid. 1 H NMR (400 MHz, DMSO-d6): δ7.60 (d, J=2.6 Hz, 2H), 7.35 (d, J=15.0 Hz, 6H), 7.13 (d, J=8.9 Hz, 2H), 5.21 (s, 4H), 5.03 (s, 4H). LCMS: No molecular ion was detected. Solution 3 Example S3-1 2-(2-(2,4-dichlorophenoxy)acetoxy)-N,N,N-trimethylethylammonium chloride
[0098] 2-Hydroxy-N,N,N-trimethylethylammonium chloride (1.46 g, 10.44 mmol) was added to CHCl 3 2,4-dichlorophenoxyacetic acid 2,4-dichlorophenoxyacetyl chloride 3 (2.5 g, 10.44 mmol) was added to the solution in CHCl (20 mL). 3 The mixture was stirred for 2 hours at 40 ℃ for 1 h. The mixture was stirred for 2 hours at 40 ℃ for 3 hours ... 1 H NMR (400 MHz, DMSO-d6): δ7.62 (d, J=2.6 Hz, 1H), 7.34 (m, 1H), 7.23 (d, J=9.0 Hz, 1H), 5.01 (s, 2H), 4.58 (s, 2H), 3.69 (m, 2H), 3.16 (s, 9H). LCMS: No molecular ion was detected. Example S3-2-Oxybis(ethane-2,1-diyl)bis(2-(2,4-dichlorophenoxy)acetate)
[0099] To a solution of 2,2'-oxydiethanol (0.24g, 2.26mmol), 2,4-dichlorophenoxyacetic acid (1g, 4.52mmol) and TEA (2.2mL g, 15.84mmol) in DCM (15mL) was added HATU (6.02g, 15.84mmol), and the resulting mixture was stirred at room temperature for 16h. After the reaction was complete, RM was concentrated in vacuo to give a crude product. Purification by flash column chromatography (silica gel; gradient elution 0-15% EtOAc: hexane) gave the title compound B2 (0.4g, 35%) as an orange oil. 1 H NMR (400 MHz, DMSO-d6): δ7.59 (d, J=2.6 Hz, 1H), 7.34 (dd, J=8.9, 2.6 Hz, 1H), 7.10 (d, J=8.9 Hz, 1H), 4.97 (s, 2H), 4.12 (m, 2H), 3.48 (m, 2H). LCMS: No molecular ion was detected. Solution 4 Example S4-1 Acetophenone O-(2-(2,4-dichlorophenoxy)acetyl)oxime
[0100] To acetophenone oxime (1 g, 7.40 mmol) in CHCl 3 To the solution in 4% paraformaldehyde (20 mL) was added NMM (2.25 g, 22.2 mmol), and the resulting mixture was stirred at room temperature for 10 min. The mixture was cooled to 0 ° C, and then 2,4-dichlorophenoxyacetyl chloride 3 (2.66 g, 11.1 mmol) was added under argon atmosphere and stirred at room temperature for 16 h. After the reaction was completed, water (50 mL) was added and the mixture was extracted with EtOAc (2x100 mL). The combined organic extracts were washed with brine and purified by Na 2 SO 4 Drying, filtering and concentration in vacuo gave the crude product. Purification by flash column chromatography (silica gel; gradient elution 0-20% EtOAc:hexanes) gave the title compound A1 (0.3 g, 11%) as a white solid. 1 H NMR (400 MHz, CDCl 3): δ7.66(m,2H),7.33(m,4H),7.17(dd,J=8.8,2.6Hz,1H),6.88(d,J=8.8Hz,1H),4.97(s,2H),2.35(s,3H). LCMS: m / z=359.67[M+Na] + .
[0101] Example S4-2 Benzaldehyde O-(2-(2,4-dichlorophenoxy)acetyl)oxime Synthesis of intermediate A2
[0102] Benzaldehyde (2 g, 18.8 mmol) was dissolved in EtOH:H 2 To the solution in O (57 mL:19 mL) were added KOAc (9.23 g, 94 mmol) and NH 2 OH.HCl (4.71 g, 56.4 mmol), and the mixture was stirred at room temperature for 10 min. The reaction mixture was heated to reflux for 5 h. After the reaction was completed, the RM was cooled to 0 ° C and the obtained solid was filtered and dried in vacuo to give intermediate A2 (1.1 g, 11%) as a white crystalline solid. Example A2 (E)-Benzaldehyde O-(2-(2,4-dichlorophenoxy)acetyl)oxime
[0103] Intermediate A2 (1 g, 8.26 mmol) was reacted with CHCl 3 To the solution in 4% paraformaldehyde (20 mL) was added NMM (2.51 g, 24.78 mmol), and the resulting mixture was stirred at room temperature for 10 min. The mixture was cooled to 0 ° C, and then 2,4-dichlorophenoxyacetyl chloride 3 (2.97 g, 12.39 mmol) was added under an argon atmosphere, and the mixture was stirred at room temperature for 16 h. After the reaction was completed, water (100 mL) was added and the mixture was extracted with EtOAc (2x100 mL). The combined organic extracts were washed with brine and purified by Na 2 SO 4 Drying, filtering and concentration in vacuo gave the crude product. Purification by flash column chromatography (silica gel; gradient elution 0-50% EtOAc:hexanes) gave the title compound A2 (0.3 g, 12%) as a white solid. 1H NMR (400MHz, DMSO-d6): δ8.76 (s, 1H), 7.70 (m, 2H), 7.46 (m, 4H), 7.39 (dd, J = 8.9, 2.6Hz, 1H), 7.23 (d, J = 8.9Hz, 1H), 5.24 (s, 2H). LCMS: m / z=345.88[M+Na] + .
[0104] Example S4-3 N'-(2-(2,4-dichlorophenoxy)acetoxy)benzamidine
[0105] To a solution of N'-benzamidine (1 g, 0.73 mmol) in THF (20 mL) was added DIPEA (3.8 mL, 2.20 mmol) at 0 °C. The mixture was stirred for 30 min, and a solution of 2,4-dichlorophenoxyacetyl chloride 3 (1.93 g, 0.80 mmol) in THF (5 mL) was added. The reaction was further warmed to room temperature and stirred for 15 h. After the reaction was complete, water (40 mL) was added; the mixture was extracted with EtOAc (2x50 mL). The combined organic extracts were washed with brine and purified by Na 2 SO 4 Drying, filtering and concentration in vacuo gave the crude product. Purification by flash column chromatography (silica gel; gradient elution 0-60% EtOAc:hexanes) gave the title compound A3 (0.44 g, 18%) as a light brown solid. 1 H NMR (400MHz, DMSO-d6): δ7.77-7.68(m,2H),7.62(d,J=2.6Hz,1H),7.57-7.33(m,4H),7.17(d,J=8.9Hz,1H),6.99(s,2H),5.16(s,2H). LCMS: m / z=338.88[M+H] + . Example S4-4 N'-(2-(2,4-dichlorophenoxy)acetoxy)nicotinamide
[0106] To a solution of N'-hydroxynicotinamide (1 g, 0.73 mmol) in THF (20 mL) was added DIPEA (3.8 mL, 2.20 mmol) at 0 °C. The mixture was stirred for 30 min, and a solution of 2,4-dichlorophenoxyacetyl chloride 3 (1.92 g, 0.80 mmol) in THF (5 mL) was added. The reaction was further warmed to room temperature and stirred for 15 h. After the reaction was complete, water (40 mL) was added; the mixture was extracted with EtOAc (2x50 mL). The combined organic extracts were washed with brine and purified by Na 2 SO 4 Drying, filtering and concentration in vacuo gave the crude product. Purification by flash column chromatography (silica gel; gradient elution 0-60% EtOAc:hexanes) gave the title compound A4 (1.18 g, 46%) as a light brown solid. 1 H NMR (400MHz, DMSO-d6): δ8.94-8.87(m,1H),8.74-8.66(m,1H),8.14-8.05(m,1H),7.62(d,J =2.6Hz,1H),7.55-7.47(m,1H),7.40(dd,J=8.9,2.6Hz,1H),7.25-7.08(m,3H),5.18(s,2H). LCMS: m / z=339.96[M+1] + . Example S4-5 N'-(2-(2,4-dichlorophenoxy)acetoxy)acetamidine
[0107] To a solution of N'-hydroxyacetamidine (1 g, 1.34 mmol) in THF (20 mL) was added DIPEA (7.04 mL, 4.04 mmol) at 0 ° C. The mixture was stirred for 30 min, and a solution of 2,4-dichlorophenoxyacetyl chloride 3 (3.56 g, 1.48 mmol) in THF (5 mL) was added. The reaction was further warmed to room temperature and stirred for 15 h. After the reaction was complete, water (40 mL) was added and the mixture was extracted with EtOAc (2x50 mL). The combined organic extracts were washed with brine and purified by Na 2 SO 4 Drying, filtering and concentration in vacuo gave the crude product. Purification by flash column chromatography (silica gel; gradient elution 0-25% EtOAc:hexanes) gave the title compound A12 (0.77 g, 21%) as a light yellow solid. 1H NMR (400MHz, DMSO-d6): δ7.60 (d, J = 2.6 Hz, 1H), 7.37 (dd, J = 8.9, 2.6 Hz, 1H), 7.10 (d, J = 8.9 Hz, 1H), 6.51 (s, 2H), 5.03 (s, 2H), 1.77 (s, 3H). LCMS: m / z=276.93[M+H] + . Example S4-6 N'-(2-(2,4-dichlorophenoxy)acetoxy)-2-phenylacetamidine
[0108] To a solution of N'-hydroxy-2-phenylacetamidine (0.94 g, 6.26 mmol) in anhydrous THF (20 mL) was added NMM (1.27 g, 12.53 mmol), and the mixture was stirred at room temperature for 10 min. The mixture was cooled to 0 ° C, and then 2,4-dichlorophenoxyacetyl chloride 3 (1 g, 4.17 mmol) was added under an argon atmosphere and stirred at room temperature for 16 h. After the reaction was complete, water (50 mL) was added; the mixture was extracted with EtOAc (2x100 mL). The combined organic extracts were washed with brine and purified by Na 2 SO 4 Drying, filtering and concentration in vacuo gave the crude product. Purification by flash column chromatography (silica gel; gradient elution 0-50% EtOAc:hexanes) gave the title compound A17 (0.33 g, 22%) as a white solid. 1 H NMR (400MHz, DMSO-d6): δ7.61 (d, J = 2.6 Hz, 1H), 7.28 (m, 5H), 7.11 (d, J = 9.0 Hz, 1H), 6.60 (s, 2H), 5.04 (s, 2H), 3.39 (s, 2H). LCMS: m / z=374.66[M+Na] + . Example S4-7 N'-(2-(2,4-dichlorophenoxy)acetoxy)benzamidine Synthesis of intermediate A5
[0109] At room temperature, furan-2-carbonitrile (1 g, 1.07 mmol) and NH 2 To a solution of OH.HCl (1.5 g, 2.14 mmol) in water (10 mL) was carefully added Na 2 CO 3(2.3 g, 2.14 mmol) in water (5 mL). The mixture was heated to reflux for 16 h. After the reaction was complete, brine (50 mL) was added; the mixture was extracted with EtOAc (4 x 50 mL). The combined organic extracts were purified by Na 2 SO 4 Drying, filtration and concentration in vacuo gave Intermediate A5 (1.2 g) as a colorless liquid. Synthesis of A5
[0110] To a solution of intermediate A5 (0.6 g, 0.47 mmol) in THF (10 mL) was added DIPEA (2.5 mL, 1.42 mmol) at 0 °C. The mixture was stirred for 30 min, and a solution of 2,4-dichlorophenoxyacetyl chloride 3 (1.26 g, 0.52 mmol) in THF (5 mL) was added. The reaction was further warmed to room temperature and stirred for 15 h. After the reaction was complete, water (40 mL) was added; the mixture was extracted with EtOAc (2x50 mL). The combined organic extracts were washed with brine and purified by Na 2 SO 4 Drying, filtering and concentration in vacuo gave the crude product. Purification by flash column chromatography (silica gel; gradient elution 0-10% EtOAc:hexanes) gave the title compound A5 (0.46 g, 30%) as a brown solid. 1 H NMR (400MHz, DMSO-d6): δ7.85(d,J=1.0Hz,1H),7.62(d,J=2.6Hz,1H),7.42-7.35(m,1H) ,7.15(d,J=9.0Hz,1H),7.09-7.02(m,1H),6.98(s,2H),6.66-6.60(m,1H),5.13(s,2H). LCMS: m / z=350.72[M+Na] + . Example S4-8 3-((2-(2,4-dichlorophenoxy)acetoxy)imino)butan-2-one
[0111] To a solution of 2,4-butanedione monoxime (0.9 g, 8.39 mmol) in acetone (20 mL) was added potassium carbonate (3.68 g, 26.67 mmol) and stirred at room temperature for 10 min. The mixture was cooled to 0 °C and then 2,4-dichlorophenoxyacetyl chloride 3 (2.13 g, 8.39 mmol) was added under an argon atmosphere and stirred at room temperature for 16 h. After the reaction was complete, water (100 mL) was added; the mixture was extracted with EtOAc (2 x 100 mL). The combined organic extracts were washed with brine and purified by Na 2 SO 4 Drying, filtering and concentration in vacuo gave the crude product. Purification by flash column chromatography (silica gel; gradient elution 0-50% EtOAc:hexanes) gave the title compound A8 (0.35 g, 13%) as a white solid. 1 H NMR (400MHz, DMSO-d6): δ7.64 (d, J = 2.6 Hz, 1H), 7.39 (dd, J = 8.9, 2.6 Hz, 1H), 7.23 (d, J = 8.9 Hz, 1H), 5.31 (s, 2H), 2.41 (s, 3H), 2.00 (s, 3H). LCMS: m / z=277.86[M+Na] + . Example S4-9 Ethyl N-2-(2,4-dichlorophenoxy)acetoxypropionimidate
[0112] To a solution of ethyl hydroxyacetimidate (0.6 g, 6.26 mmol) in anhydrous THF (20 mL) was added NMM (1.26 g, 12.53 mmol) and stirred at room temperature for 10 min. The mixture was cooled to 0 ° C, and then 2,4-dichlorophenoxyacetyl chloride 3 (1 g, 4.17 mmol) was added under an argon atmosphere and stirred at room temperature for 16 h. After the reaction was complete, water (100 mL) was added; the mixture was extracted with EtOAc (2x100 mL). The combined organic extracts were washed with brine and purified by Na 2 SO 4 Drying, filtering and concentration in vacuo gave the crude product. Purification by flash column chromatography (silica gel; gradient elution 0-50% EtOAc:hexanes) gave the title compound A9 (0.8 g, 64%) as a white solid. 1H NMR (400MHz, DMSO-d6): δ7.62(d,J=2.6Hz,1H),7.38(dd,J=8.9,2.6Hz,1H),7.17(d, J=8.9Hz,1H),5.13(s,2H),4.11(q,J=7.0Hz,2H),2.00(s,3H),1.27(t,J=7.1Hz,3H). LCMS: m / z=305.94[M+H] + . Example S4-10 Methyl N-2-(2,4-dichlorophenoxy)acetoxythioacetimidate Synthesis of intermediate A10-1
[0113] A solution of acetaldehyde oxime (10 g, 169 mmol) in DMF (250 mL) was stirred at room temperature for 10 min. The mixture was cooled to 0 ° C, and N-chlorosuccinimide (22.6 g, 169 mmol) was added four times within 30 min; the resulting mixture was stirred at room temperature for 16 h. After the reaction was complete, ice water: brine mixture (200 mL: 200 mL) was added and stirred for 10 min. The mixture was extracted with EtOAc (2x150 mL); the combined organic extracts were washed with brine and purified by Na 2 SO 4 Drying, filtration and concentration in vacuo gave intermediate A10-1 (0.35 g, 13%) as a white solid. Synthesis of intermediate A10-2
[0114] To a solution of acetyl chloride oxime intermediate A10-1 (9.5 g, 101.6 mmol) in MeOH (100 mL) was added a solution of sodium thiomethoxide (16.84 g, 240.5 mmol) in MeOH (150 mL) at 0°C and the RM was stirred at room temperature for 16 h. After the reaction was complete, EtOAc (300 mL) was added and the RM was filtered to remove solids. The filtrate was purified by Na 2 SO 4 Drying, filtering and concentration in vacuo gave intermediate A10-2 (5.2 g) as a yellow solid. Synthesis of A10
[0115] Intermediate A10-2 (500 mg, 3.907 mmol) was reacted with CHCl 3To the solution in 4% paraformaldehyde (20 mL) was added NMM (1.29 mL, 11.7 mmol), and the mixture was stirred at room temperature for 10 min. The mixture was cooled to 0 ° C, and then 2,4-dichlorophenoxyacetyl chloride 3 (1.4 g, 5.86 mmol) was added under argon atmosphere, and the mixture was stirred at room temperature for 16 h. After the reaction was completed, water (100 mL) was added and the mixture was extracted with EtOAc (2x100 mL). The combined organic extracts were washed with brine and purified by Na 2 SO 4 Drying, filtering and concentration in vacuo gave the crude product. Purification by flash column chromatography (silica gel; gradient elution 0-50% EtOAc:hexanes) gave the title compound A10 (0.39 g, 12%) as a white solid. 1 H NMR (400 MHz, CDCl 3 ): δ7.39(d,J=2.6Hz,1H),7.17(dd,J=8.8,2.6Hz,1H),6.86(d,J=8.8Hz,1H),4.84(s,2H),2.39(s,3H),2.29(s,3H). LCMS: m / z=329.73[M+Na] + . Example S4-11 N-(2-(2,4-dichlorophenoxy)acetoxy)iminophenylacetonitrile
[0116] To a solution of N-hydroxyiminobenzeneacetonitrile (1 g, 0.68 mmol) in THF (20 mL) was added DIPEA (3.6 mL, 2.05 mmol) at 0 °C. The mixture was stirred for 30 min, and a solution of 2,4-dichlorophenoxyacetyl chloride 3 (1.8 g, 0.75 mmol) in THF (5 mL) was added. The reaction was further warmed to room temperature and stirred for 15 h. After the reaction was complete, water (40 mL) was added; the mixture was extracted with EtOAc (2x50 mL). The combined organic extracts were washed with brine and purified by Na 2 SO 4 Drying, filtering and concentration in vacuo gave the crude product. Purification by flash column chromatography (silica gel; gradient elution 0-20% EtOAc:hexanes) gave the title compound A6 (0.52 g, 22%) as a light brown solid. 1 H NMR (400 MHz, DMSO-d6): δ7.95-7.89 (m, 2H), 7.76-7.69 (m, 1H), 7.68-7.60 (m, 3H), 7.41-7.36 (m, 1H), 7.34-7.29 (m, 1H), 5.41 (s, 2H) LCMS: no molecular ion was detected. Example S4-12 Diethyl 2-((2-(2,4-dichlorophenoxy)acetoxy)imino)malonate
[0117] To a solution of diethyl 2-(hydroxyimino)malonate (1 g, 0.52 mmol) in DCM (20 mL) was added TEA (1.2 mL, 0.89 mmol) at 0 °C. The mixture was stirred for 30 min, and a solution of 2,4-dichlorophenoxyacetyl chloride 3 (2.2 g, 0.89 mmol) in THF (5 mL) was added. The reaction was further warmed to room temperature and stirred for 3 h. After the reaction was complete, water (40 mL) was added; the mixture was extracted with EtOAc (2x50 mL). The combined organic extracts were washed with brine and purified by Na 2 SO 4 Drying, filtering and concentration in vacuo gave the crude product. Purification by flash column chromatography (silica gel; gradient elution 0-20% EtOAc:hexanes) followed by recrystallization from hexanes:MTBE gave the title compound A7 (0.32 g, 16%) as a white solid. 1 H NMR (400 MHz, DMSO-d6): δ7.63 (d, J=2.5 Hz, 1H), 7.38 (dd, J=8.9, 2.5 Hz, 1H), 7.23 (d, J=9.0 Hz, 1H), 5.26 (s, 2H), 4.50-4.18 (m, 4H), 1.41-1.13 (m, 6H). LCMS: No molecular ion was detected. Example S4-13 (1,1')-4-(-((2-(2,4-dichlorophenoxy)acetyloxy)imino)methyl)benzaldehyde-O-(2-(2,4-dichlorophenoxy)acetyl)oxime
[0118] To a solution of 4-((hydroxyimino)methyl)benzaldehyde oxime (1 g, 0.60 mmol) in THF (40 mL) was added NMM (4.5 mL, 4.08 mmol) at 0 °C. The mixture was stirred for 30 min, and a solution of 2,4-dichlorophenoxyacetyl chloride 3 (8.7 g, 3.65 mmol) in THF (5 mL) was added. The reaction was further warmed to room temperature and stirred for 15 h. After the reaction was complete, water (40 mL) was added; the mixture was extracted with EtOAc (2x50 mL). The combined organic extracts were washed with brine and purified by Na 2 SO 4Drying, filtering and concentration in vacuo gave the crude product. Purification by flash column chromatography (silica gel; gradient elution 0-60% EtOAc:hexanes) followed by trituration with MeOH gave the title compound B3 (0.75 g, 22%) as an off-white solid. 1 H NMR (400 MHz, DMSO-d6): δ8.83 (s, 2H), 7.94 (s, 4H), 7.63 (d, J = 2.4 Hz, 2H), 7.43-7.34 (m, 2H), 7.24 (d, J = 8.9 Hz, 2H), 5.26 (s, 4H). LCMS: No molecular ion was detected. Example S4-14 (2,4)-Pentane-2,4-dione O,O-bis(2-(2,4-dichlorophenoxy)acetyl)dioxime
[0119] To a solution of 2,4-pentanedione dioxime (0.82 g, 6.27 mmol) in anhydrous THF (20 mL) was added NMM (1.27 g, 12.53 mmol) and stirred at room temperature for 10 min. The mixture was cooled to 0 °C and then 2,4-dichlorophenoxyacetyl chloride (1 g, 4.17 mmol) was added under an argon atmosphere and stirred at room temperature for 16 h. After the reaction was complete, water (100 mL) was added; the mixture was extracted with EtOAc (2 x 100 mL). The combined organic extracts were washed with brine and purified by Na 2 SO 4 Drying, filtering and concentration in vacuo gave the crude product. Purification by flash column chromatography (silica gel; gradient elution 0-50% EtOAc:hexanes) gave the title compound B6 (0.35 g, 11%) as a white solid. 1 H NMR (400MHz, DMSO-d6): δ7.62 (d, J = 2.5 Hz, 2H), 7.37 (dd, J = 8.9, 2.6 Hz, 2H), 7.15 (m, 2H), 5.15 (s, 4H), 3.46 (s, 2H), 1.98 (s, 6H). LCMS: m / z=558.32[M+Na] + . Solution 5 Example S5-1(1,4)-N' 1 ,N' 4 -Bis(2-(2,4-dichlorophenoxy)acetoxy)terephthalamide Synthesis of intermediate B5
[0120] To a solution of 1,4-cyanobenzene (2.5 g, 19.51 mmol) in ethanol (45 mL) was added hydroxylamine (50% by weight) in water (3.75 mL) and heated to reflux at room temperature for 16 h. After completion of the reaction, the solid was collected by filtration to give Intermediate B5 (1 g) as a white solid. Synthesis of B5
[0121] To a solution of intermediate B5 (0.95 g, 4.89 mmol) in anhydrous THF (200 mL) was added DIPEA (25.7 mL, 48.9 mmol), and the resulting mixture was stirred at room temperature for 10 min. The mixture was cooled to 0 ° C, and then 2,4-dichlorophenoxyacetyl chloride 3 (6.8 g, 36.67 mmol) was added under an argon atmosphere, and the reaction mixture was stirred for 16 h. After the reaction was completed, the obtained solid was collected by filtration to give the title compound B5 (0.5 g, 17%) as an off-white solid. 1 H NMR (400 MHz, DMSO-d6): δ7.82 (d, J=7.1 Hz, 4H), 7.62 (d, J=2.6 Hz, 2H), 7.40 (dd, J=8.9, 2.6 Hz, 2H), 7.17 (d, J=9.0 Hz, 2H), 7.09 (s, 4H), 5.17 (s, 4H). LCMS: No molecular ion was detected. Solution 6 Example S6-1 N-(2-(2,4-dichlorophenoxy)acetoxy)benzamide
[0122] To a solution of N-hydroxybenzamide (0.62 g, 4.52 mmol), 2,4-dichlorophenoxyacetic acid (1 g, 4.52 mmol), TEA (2.2 mL g, 15.84 mmol) in DCM (15 mL) was added HATU (2.58 g, 6.78 mmol), and the reaction mixture was stirred at room temperature for 16 h. After the reaction was complete, water (40 mL) was added; the mixture was extracted with DCM (2x50 mL). The combined organic extracts were washed with brine and purified by Na 2 SO 4 Drying, filtering and concentration in vacuo gave the crude product. Purification by flash column chromatography (silica gel; gradient elution 0-20% EtOAc:hexanes) gave the title compound A40 (0.35 g, 23%) as a white solid. 1H NMR (400 MHz, DMSO-d6): δ10.16 (s, 1H), 7.57 (m, 3H), 7.28 (m, 3H), 7.05 (m, 2H), 4.86 (s, 2H). LCMS: No molecular ion was detected. Example S6-2 N-(2-(2,4-dichlorophenoxy)acetoxy)-N-methylbenzamide Synthesis of intermediate A16
[0123] To a solution of N-methylhydroxylamine hydrochloride (1.62 g, 19.4 mmol), DMAP (0.16 g, 1.29 mmol) in DCM (10 mL) was added triethylamine (3.92 g, 38.7 mmol) at room temperature and stirred for 10 min. The reaction mixture was cooled to 0 °C and then benzoyl chloride (1.81 g, 12.9 mmol) was added dropwise and the RM was stirred at room temperature for 16 h. After the reaction was complete, water (50 mL) was added; the mixture was extracted with DCM (2x50 mL). The combined organic extracts were washed with brine and purified by Na 2 SO 4 Drying, filtering and concentration in vacuo gave the crude product. Purification by flash column chromatography (silica gel; gradient elution 0-50% EtOAc:hexanes) gave intermediate A16 (1 g) as a white solid. Synthesis of A16
[0124] To a solution of intermediate A16 (0.63 g, 4.17 mmol) in THF (20 mL) was added DIPEA (2.2 mL, 12.52 mmol) at 0 °C. The mixture was stirred for 30 min, and a solution of 2,4-dichlorophenoxyacetyl chloride 3 (1.00 g, 4.17 mmol) in THF (5 mL) was added. The reaction was further warmed to room temperature and stirred for 3 h. After the reaction was complete, water (40 mL) was added; the mixture was extracted with EtOAc (2x50 mL). The combined organic extracts were washed with brine and purified by Na 2 SO 4 Drying, filtering and concentration in vacuo gave the crude product. Purification by flash column chromatography (silica gel; gradient elution 0-15% EtOAc:hexanes) gave the title compound A16 (0.45 g, 31%) as an off-white solid. 1H NMR (400MHz, DMSO-d6): δ7.41 (m, 6H), 7.20 (dd, J = 8.9, 2.6Hz, 1H), 6.63 (d, J = 8.9Hz, 1H), 5.07 (s, 2H), 3.42 (s, 3H). LCMS: m / z=375.66[M+Na] + . Example S6-3 N-(2-(2,4-dichlorophenoxy)acetoxy)-2-phenylacetamide Synthesis of intermediate A13-1
[0125] Hydroxylamine hydrochloride (9 g, 129.37 mmol) was added to K 2 CO 3 (18 g, 129.37 mmol) in EtOAc (200 mL) and H 2 The resulting solution was cooled to 0 °C and then phenylacetyl chloride (10 g, 64.68 mmol) dissolved in a minimum amount of EtOAc was added dropwise. The reaction was stirred for 2 h while warming to room temperature. The phases were separated and the aqueous phase was extracted with EtOAc (2 x 100 mL). The combined organic extracts were purified by Na 2 SO 4 Drying, filtration and concentration in vacuo gave intermediate A13-1 (8 g) as a white solid. Synthesis of A13
[0126] To a solution of 2,4-dichlorophenoxyacetic acid (0.28 g, 1.26 mmol) in DCM (7 mL) was added DMAP (0.31 g, 2.52 mmol), intermediate A13-1 (0.2 g, 1.32 mmol) and EDC·HCl (0.48 g, 2.52 mmol) and stirred at room temperature for 16 h. After the reaction was complete, water (100 mL) was added; the mixture was extracted with EtOAc (2 x 100 mL). The combined organic extracts were washed with brine and purified by Na 2 SO 4 Drying, filtering and concentration in vacuo gave the crude product. Purification by flash column chromatography (silica gel; gradient elution 0-25% EtOAc:hexanes) gave the title compound A13 (1 g, 43%) as a white solid. 1H NMR (400MHz, DMSO-d6): δ12.21 (s, 1H), 7.62 (d, J = 2.6Hz, 1H), 7.38 (dd, J = 8. 9, 2.6Hz, 1H), 7.21 (m, 5H), 7.16 (d, J = 8.9Hz, 1H), 5.21 (s, 2H), 3.51 (s, 2H). LCMS: m / z=375.88[M+Na] + . Example S6-4 N 1 ,N 4 -Bis(2-(2,6-dichlorophenoxy)acetoxy)terephthalamide Synthesis of intermediate B4-1
[0127] Terephthaloyl chloride (2.00 g, 10 mmol) was dissolved in THF:H 2 O (15mL:1.5mL) was added with NaHCO 3 (3.7 g, 44 mmol), followed by the addition of NH 2 OH·HCl (1.53 g, 22 mmol) was added and stirred in an ice bath for 1 hour. Afterwards, the phases were separated and the aqueous phase was extracted with EtOAc (2 x 100 mL). The combined organic extracts were purified by Na 2 SO 4 Drying, filtering and concentrating in vacuo gave intermediate B4-1 (2 g) as a white solid. Synthesis of intermediate B4-2
[0128] To a solution of intermediate B4-1 (2 g, 10.2 mmol) in MeOH (50 mL) was added NaOH (0.8 g, 20 mmol), and the mixture was stirred at room temperature for 2 h. The obtained solid was filtered and dried in vacuo to give intermediate B4-2 (2 g) as a white solid. Synthesis of B4
[0129] To a solution of intermediate B4-2 (0.5 g, 2.08 mmol) in 1,4-dioxane (6 mL) was added 2,4-dichlorophenoxyacetyl chloride 3 (1.7 g, 4.58 mmol) and stirred at room temperature for 16 h. After the reaction was complete, water (100 mL) was added and the mixture was extracted with EtOAc (2 x 100 mL). The combined organic extracts were washed with brine and purified by Na 2 SO 4Drying, filtering and concentration in vacuo gave the crude product. Purification by flash column chromatography (silica gel; gradient elution 0-50% EtOAc:hexanes) gave the title compound B4 (0.4 g, 26%) as a white solid. 1 H NMR (400MHz, DMSO-d6): δ12.85 (s, 2H), 7.96 (s, 4H), 7.64 (d, J = 2.6 Hz, 2H), 7.43 (dd, J = 8.9, 2.5 Hz, 2H), 7.23 (d, J = 8.9 Hz, 2H), 5.33 (s, 4H). LCMS: m / z=601.80[M+H] + . Example S6-5 2-(2,4-dichlorophenoxy)acetic acid piperidin-1-yl ester
[0130] To a solution of N-hydroxypiperidine (1 g, 9.89 mmol) in DMF (10 mL) was added K 2 CO 3 (4.1 g, 29.67 mmol). The mixture was stirred for 10 min, and a solution of 2,4-dichlorophenoxyacetyl chloride 3 (2.84 g, 11.86 mmol) in DMF (3 mL) was added. The reaction was further warmed to room temperature and stirred for 4 h. After the reaction was complete, water (40 mL) was added and the mixture was extracted with EtOAc (2 x 50 mL). The combined organic extracts were washed with brine and purified by Na 2 SO 4 Drying, filtering and concentration in vacuo gave the crude product. Purification by flash column chromatography (silica gel; gradient elution 0-30% EtOAc:hexanes) gave the title compound A11 (0.3 g, 5%) as a white solid. 1 H NMR (400 MHz, CDCl 3 ): δ7.39(d,J=2.5Hz,1H),7.16(dd,J=8.8,2.5Hz,1H),6.82(d,J=8.8Hz,1H), 4.70(s,2H),3.36(s,2H),2.65(s,2H),1.70(m,4H),1.61(s,1H),1.23(s,1H). LCMS: m / z=303.86[M+H] + . Example S6-6 N,N-dibenzyl-O-(2-(2,4-dichlorophenoxy)acetyl)hydroxylamine
[0131] To a solution of N,N-dibenzylhydroxylamine (1 g, 4.68 mmol) in THF (20 mL) was added DIPEA (2.45 mL, 14.04 mmol) at 0 °C. The mixture was stirred for 30 min, and a solution of 2,4-dichlorophenoxyacetyl chloride 3 (1.00 g, 5.15 mmol) in THF (5 mL) was added. The reaction was further warmed to room temperature and stirred for 1 h. After the reaction was complete, water (40 mL) was added; the mixture was extracted with EtOAc (2x50 mL). The combined organic extracts were washed with brine and purified by Na 2 SO 4 Drying, filtering and concentration in vacuo gave the crude product. Purification by flash column chromatography (silica gel; gradient elution 0-07% EtOAc:hexanes) gave the title compound A14 (0.7 g, 37%) as a white solid. 1 H NMR (400 MHz, CDCl 3 ):δ7.30(m,10H),7.28(d,J=2.3Hz,1H),6.83(dd,J=8.8,2.3Hz,1H),5.68(d,J=8.8Hz,1H),4.32(s,2H),4.10(s,4H)LCMS:No molecular ion was detected. Example S6-7 2-(2,4-dichlorophenoxy)acetic acid 1,3-dioxoisoindolin-2-yl ester
[0132] To a solution of 2-hydroxyisoindoline-1,3-dione (1 g, 6.13 mmol) in THF (20 mL) was added DIPEA (3.2 mL, 18.39 mmol) at 0 °C. The mixture was stirred for 30 min, and a solution of 2,4-dichlorophenoxyacetyl chloride 3 (1.62 g, 6.74 mmol) in THF (5 mL) was added. The reaction was further warmed to room temperature and stirred for 1 h. After the reaction was complete, water (40 mL) was added; the mixture was extracted with EtOAc (2x50 mL). The combined organic extracts were washed with brine and purified by Na 2 SO 4 Drying, filtering and concentration in vacuo gave the crude product. Purification by flash column chromatography (silica gel; gradient elution 0-07% EtOAc:hexanes) gave the title compound A15 (1 g, 45%) as an off-white solid. 1 H NMR (400 MHz, CDCl 3):δ7.86(m,2H),7.74(m,2H),7.41(d,J=2.5Hz,1H),7.21(m,1H),6.96(d,J=8.8Hz,1H),5.10(s,2H)LCMS:No molecular ion was detected. Solution 7 Example 7-12-(2,4-dichlorophenoxy)-N-toluenesulfonyl acetamide
[0133] To a solution of 2,4-dichlorophenoxyacetic acid (5 g, 22.62 mmol) in DCM (130 mL) was added DMAP (5.54 g, 45.24 mmol), p-toluoylsulfonamide (4.07 g, 23.75 mmol) and EDC·HCl (8.67 g, 45.24 mmol), and the resulting mixture was stirred at room temperature for 4 h. After the reaction was complete, water (100 mL) was added; the mixture was extracted with EtOAc (2 x 100 mL). The combined organic extracts were washed with brine and purified by Na 2 SO 4 Drying, filtering and concentration in vacuo gave the crude product. Purification by flash column chromatography (silica gel; gradient elution 0-25% EtOAc:hexanes) gave the title compound D32 (0.80 g, 9%) as a white solid. 1 H NMR (400MHz, DMSO-d6): δ12.44(s,1H),7.81(d,J=8.2Hz,2H),7.56(d,J=2.5Hz,1H),7.43(d ,J=8.1Hz,2H),7.28(dd,J=8.9,2.6Hz,1H),6.87(d,J=8.9Hz,1H),4.79(s,2H),2.40(s,3H). LCMS: m / z=374.09[M+H] + . Solution 8 Example S8-1 N-(4-chlorophenyl)-2-(2,4-dichlorophenoxy)acetamide
[0134] To a solution of 4-chloroaniline (0.5 g, 3.92 mmol) in anhydrous DCM (20 mL) was added TEA (1.1 g, 11.75 mmol) at 0 °C. The mixture was stirred for 10 min, and a solution of 2,4-dichlorophenoxyacetyl chloride 3 (0.93 g, 3.90 mmol) in DCM (3 mL) was added. The reaction was further warmed to room temperature and stirred for 16 h. After the reaction was complete, water (50 mL) was added; the mixture was extracted with EtOAc (2x50 mL). The combined organic extracts were washed with brine and purified by Na 2 SO 4 Drying, filtering and concentration in vacuo gave the crude product. Purification by flash column chromatography (silica gel; gradient elution 0-50% EtOAc:hexanes) gave the title compound D6 (0.37 g, 29%) as an off-white solid. 1 H NMR (400MHz, DMSO-d6): δ10.31 (s, 1H), 7.49 (m, 3H), 7.24 (m, 3H), 7.11 (d, J = 8.9Hz, 1H), 4.87 (s, 2H). LCMS: m / z=331.72[M+H] + . Example S8-2 2-(2,4-dichlorophenoxy)-N-(pyridin-4-yl)acetamide
[0135] To a solution of 4-aminopyridine (1.0 g, 10.63 mol) in anhydrous DCM (30 mL) was added TEA (3.23 g, 31.89 mmol) at 0 °C. The mixture was stirred for 10 min, and a solution of 2,4-dichlorophenoxyacetyl chloride 3 (2.54 g, 10.63 mmol) in DCM (3 mL) was added. The reaction was further warmed to room temperature and stirred for 16 h. After the reaction was complete, water (50 mL) was added; the mixture was extracted with EtOAc (2x50 mL). The combined organic extracts were washed with brine and purified by Na 2 SO 4 Drying, filtering and concentration in vacuo gave the crude product. Purification by flash column chromatography (silica gel; gradient elution 0-50% EtOAc:hexanes) gave the title compound D1 (0.95 g, 30%) as an off-white solid. 1 H NMR (DMSO-d6): δ10.58 (s, 1H), 8.45 (d, J = 5.9 Hz, 2H), 7.73-7.49 (m, 3H), 7.47-7.21 (m, 1H), 7.12 (d, J = 8.9 Hz, 1H), 4.92 (s, 2H). LCMS: m / z=296.84[M+H] + . Example S8-3 2-(2,4-dichlorophenoxy)-N-(isoxazol-3-yl)acetamide
[0136] To a solution of 3-aminoisoxazole (1.0 g, 11.89 mol) in anhydrous DCM (30 mL) was added TEA (3.6 g, 35.67 mmol) at 0 °C. The mixture was stirred for 10 min, and a solution of 2,4-dichlorophenoxyacetyl chloride 3 (2.8 g, 11.89 mmol) in DCM (3 mL) was added. The reaction was further warmed to room temperature and stirred for 16 h. After the reaction was complete, water (50 mL) was added; the mixture was extracted with EtOAc (2x50 mL). The combined organic extracts were washed with brine and purified by Na 2 SO 4 Drying, filtering and concentration in vacuo gave the crude product. Purification by flash column chromatography (silica gel; gradient elution 0-50% EtOAc:hexanes) gave the title compound D2 (1 g, 30%) as an off-white solid. 1 H NMR (400MHz, DMSO-d6): δ11.33(s,1H),8.83(d,J=1.7Hz,1H),7.61(d,J=2.5Hz,1H),7 .37(dd,J=8.9,2.6Hz,1H),7.09(d,J=8.9Hz,1H),6.91(d,J=1.7Hz,1H),4.95(s,2H). LCMS: m / z=286.78[M+H] + . Solution 9 Example S9-1 4-Chlorophenyl 2-(2,4-dichlorophenoxy)acetate
[0137] To a solution of 4-chlorophenol (1 g, 7.77 mmol) in THF (20 mL) was added DIPEA (4.1 mL, 23.31 mmol) at 0 °C. The mixture was stirred for 30 min, and a solution of 2,4-dichlorophenoxyacetyl chloride 3 (2.04 g, 8.55 mmol) in THF (5 mL) was added. The reaction was further warmed to room temperature and stirred for 15 h. After the reaction was complete, water (40 mL) was added; the mixture was extracted with EtOAc (2x50 mL). The combined organic extracts were washed with brine and purified by Na 2 SO 4Drying, filtering and concentration in vacuo gave the crude product. Purification by flash column chromatography (silica gel; gradient elution 0-10% EtOAc:hexanes) gave the title compound E5 (0.36 g, 14%) as a brown solid. 1 H NMR (400 MHz, DMSO-d6): δ7.63 (d, J=2.5 Hz, 1H), 7.55-7.49 (m, 2H), 7.42-7.37 (m, 1H), 7.33-7.28 (m, 1H), 7.28-7.22 (m, 2H), 5.25 (s, 2H). LCMS: No molecular ion was detected. Example S9-2 2-(2,4-dichlorophenoxy)acetic acid pyrimidin-5-yl ester
[0138] To a solution of pyrimidin-5-ol (0.5 g, 5.20 mmol) in THF (20 mL) was added a solution of 2,4-dichlorophenoxyacetyl chloride 3 (1.25 g, 5.20 mmol) in THF (5 mL). The reaction was further stirred at room temperature for 3 h. After the reaction was complete, water (40 mL) was added; the mixture was extracted with EtOAc (2 x 50 mL). The combined organic extracts were washed with brine and purified by Na 2 SO 4 Drying, filtering and concentration in vacuo gave the crude product. Purification by flash column chromatography (silica gel; gradient elution 0-45% EtOAc:hexanes) gave the title compound E14 (0.36 g, 24%) as a white solid. 1 H NMR (400MHz, DMSO-d6): δ9.15 (s, 1H), 8.83 (s, 2H), 7.64 (d, J = 2.4Hz, 1H), 7.31 (m, 2H), 5.32 (s, 2H). LCMS: m / z=298.73[M+H] + . Example S9-3 2-(2,4-dichlorophenoxy)acetic acid 1,3-dimethyl-1H-pyrazol-5-yl ester
[0139] To a solution of 1,3-dimethyl-1H-pyrazole-5-ol (2 g, 17.8 mmol), 2,4-dichlorophenoxyacetyl chloride 3 (3.94 g, 17.84 mmol) and TEA (8.5 mL g, 62.44 mmol) in DMF (50 mL) was added HATU (17 g, 35.68 mmol), and the reaction mixture was stirred at room temperature for 3 h. After the reaction was complete, ice-cold water (100 mL) was added; the obtained solid was filtered and dried in vacuo to give the title compound E6 (0.36 g, 24%) as a white solid. 1 H NMR (400 MHz, DMSO-d6): δ7.64 (d, J=2.5 Hz, 1H), 7.40 (dd, J=8.9, 2.5 Hz, 1H), 7.34-7.19 (m, 1H), 5.91 (s, 1H), 5.34 (s, 2H), 3.56 (s, 3H), 2.11 (s, 3H). LCMS: No molecular ion was detected. Example S9-4 2-(2,4-dichlorophenoxy)-1-(2-hydroxy-1-methyl-1H-indol-3-yl)ethanone
[0140] To a solution of 1-methyl-1H-indol-2-ol (0.5 g, 2.03 mmol), 2,4-dichlorophenoxyacetyl chloride 3 (0.54 g, 2.24 mmol) in dioxane (10 mL) was added KOtBu (0.7 g, 6.11 mmol). The reaction mixture was then heated at 80 °C for 6 h. After the reaction was complete, water (40 mL) was added and the mixture was extracted with EtOAc (2 x 50 mL). The combined organic extracts were washed with brine and purified by Na 2 SO 4 Drying, filtering and concentration in vacuo gave the crude product. Purification by flash column chromatography (silica gel; gradient elution 0-30% EtOAc:hexanes) gave the title compound C1 (0.14 g, 20%) as a brown solid. 1 H NMR (400 MHz, DMSO-d6): δ12.31 (s, 1H), 7.74 (d, J = 6.4 Hz, 1H), 7.62 (d, J = 2.6 Hz, 1H), 7.36 (m, 1H), 7.30 (d, J = 8.9 Hz, 1H), 7.16 (m, 1H), 6.92 (m, 2H), 5.52 (s, 2H), 3.20 (s, 3H). LCMS: No molecular ion was detected. Solution 10 Example S10-1 2-(2,4-dichlorophenoxy)-N-phenoxyacetamide
[0141] To a solution of O-phenylhydroxylamine (0.5 g, 4.17 mmol) in DCM (10 mL) was added TEA (0.9 mL, 6.25 mmol) at 0 °C. The mixture was stirred for 30 min, and a solution of 2,4-dichlorophenoxyacetyl chloride 3 (1 g, 4.17 mmol) in THF (5 mL) was added. The reaction was further warmed to room temperature and stirred for 15 h. After the reaction was complete, water (40 mL) was added; the mixture was extracted with EtOAc (2x50 mL). The combined organic extracts were washed with brine and purified by Na 2 SO 4 Drying, filtering and concentration in vacuo gave the crude product. Purification by flash column chromatography (silica gel; gradient elution 0-30% EtOAc:hexanes) gave the title compound D7 (0.75 g, 52%) as a light yellow solid. 1 H NMR (400MHz, DMSO-d6): δ12.21(s,1H),7.62(d,J=2.0Hz,1H),7.43(d,J=7.7Hz,1H),7.34(t,J =7.6Hz, 2H), 7.18 (d, J = 8.6Hz, 1H), 7.04 (d, J = 6.5Hz, 3H), 4.84 (s, 2H) LCMS: m / z = 333.98 [M+Na] + . Example S10-2 N-(Benzyloxy)-2-(2,4-dichlorophenoxy)acetamide
[0142] To a solution of O-benzylhydroxylamine (0.5 g, 4.17 mmol) in DCM (10 mL) was added TEA (0.9 mL, 6.25 mmol) at 0 ° C. The mixture was stirred for 30 min, and a solution of 2,4-dichlorophenoxyacetyl chloride 3 (1 g, 4.17 mmol) in DCM (5 mL) was added. The reaction mixture was allowed to warm to room temperature and stirred for 15 h. After the reaction was complete, water (40 mL) was added and the mixture was extracted with EtOAc (2x50 mL). The combined organic extracts were washed with brine and purified by Na 2 SO 4 Drying, filtering and concentration in vacuo gave the crude product. Purification by flash column chromatography (silica gel; gradient elution 0-30% EtOAc:hexanes) gave the title compound D8 (0.5 g, 37%) as a white solid. 1H NMR (400MHz, DMSO-d6): δ11.41(s,1H),7.60(s,1H),7.39(d,J=6.3Hz,6H),7.04(d,J=8.9Hz,1H),4.83(s,2H),4.60(s,2H). LCMS: m / z=347.83[M+Na] + . Example S10-3 2-(2,4-dichlorophenoxy)-N'-methyl-N'-phenylacetohydrazide
[0143] To a solution of 1-methyl-1-phenylhydrazine (0.5 g, 4.17 mmol) in DCM (10 mL) was added TEA (1.75 mL, 12.5 mmol) at 0 °C. The mixture was stirred for 30 min, and then a solution of 2,4-dichlorophenoxyacetyl chloride 3 (1 g, 4.17 mmol) in DCM (5 mL) was added. The reaction mixture was allowed to warm to room temperature and stirred for 15 h. After the reaction was complete, water (40 mL) was added; the mixture was extracted with EtOAc (2x50 mL). The combined organic extracts were washed with brine and purified by Na 2 SO 4 Drying, filtering and concentration in vacuo gave the crude product. Purification by flash column chromatography (silica gel; gradient elution 0-25% EtOAc:hexanes) gave the title compound D11 (0.3 g, 37%) as a brown solid. 1 H NMR (400MHz, DMSO-d6): δ10.21(s,1H),7.62(d,J=2.6Hz,1H),7.43(dd,J=8.9 ,2.6Hz,1H),7.24-7.11(m,3H),6.83-6.73(m,3H),4.79(s,2H),3.09(s,3H). LCMS: m / z=324.76[M+H] + . Example S10-4 N'-(2-(2,4-dichlorophenoxy)acetyl)-N-methylbenzohydrazide
[0144] To a solution of N-methylbenzohydrazide (0.69 g, 4.17 mmol) in DCM (10 mL) was added TEA (0.9 mL, 6.25 mmol) at 0 °C. The mixture was stirred for 30 min, and a solution of 2,4-dichlorophenoxyacetyl chloride 3 (1 g, 4.17 mmol) in DCM (5 mL) was added. The reaction mixture was allowed to warm to room temperature and stirred for 15 h. After the reaction was complete, water (40 mL) was added; the mixture was extracted with EtOAc (2x50 mL). The combined organic extracts were washed with brine and purified by Na 2 SO 4 Drying, filtering and concentration in vacuo gave the crude product. Purification by flash column chromatography (silica gel; gradient elution 0-30% EtOAc:hexanes) gave the title compound D9 (0.3 g, 20%) as a white solid. 1 H NMR (400MHz, DMSO-d6): δ10.79(s,1H),7.55(s,1H),7.52-7.41(m,3H),7.38(d,J= 7.1Hz, 2H), 7.10 (d, J = 7.4Hz, 1H), 6.38 (d, J = 7.9Hz, 1H), 4.54 (s, 2H), 3.13 (s, 3H). LCMS: m / z=352.84[M+H] + . Solution 11 Example S11-1 2-(2,4-dichlorophenoxy)-1-(1H-indazol-1-yl)ethanone
[0145] To a solution of 1H-indazole (0.5 g, 4.23 mmol) in anhydrous DCM (10 mL) was added TEA (0.85 g, 8.46 mmol) at 0 °C. The mixture was stirred for 10 min, and a solution of 2,4-dichlorophenoxyacetyl chloride 3 (1.5 g, 6.34 mmol) in DCM (3 mL) was added. The reaction was allowed to warm to room temperature and stirred for 16 h. After the reaction was complete, water (50 mL) was added; the mixture was extracted with EtOAc (2x50 mL). The combined organic extracts were washed with brine and purified by Na 2 SO 4 Drying, filtering and concentration in vacuo gave the crude product. Purification by flash column chromatography (silica gel; gradient elution 0-50% EtOAc:hexanes) gave the title compound D3 (0.31 g, 23%) as a light brown solid. 1H NMR (400MHz, DMSO-d6): δ8.60 (d, J=0.8Hz, 1H), 8.28 (dq, J=8.4, 0.9Hz, 1H), 7.97 (dt, J=8 .0,1.0Hz,1H),7.60(m,2H),7.48(ddd,J=8.0,7.1,0.9Hz,1H),7.23(m,2H),5.81(s,2H). LCMS: m / z=320.73[M+H] + . Example S11-2 1-(1H-benzo[d]imidazol-1-yl)-2-(2,4-dichlorophenoxy)ethanone
[0146] HATU (12.9 g, 33.93 mmol) was added to a solution of 1H-benzo [d] imidazole (2.67 g, 22.62 mmol), 2,4- (dichlorophenoxy) acetic acid (5 g, 22.62 mmol) and TEA (7.7 mL g, 56.56 mmol) in DMF (50 mL). The reaction mixture was stirred at room temperature for 16 h. After the reaction was complete, water (40 mL) was added; the precipitated solid was collected by suction filtration and suction dried to give a crude product. Purification by trituration with hexane: MTBE gave the title compound D4 (2.5 g, 34%) as an off-white solid. 1 H NMR (400 MHz, DMSO-d6): δ8.94 (s, 1H), 8.08 (m, 1H), 7.75 (m, 1H), 7.65 (d, J=2.3 Hz, 1H), 7.28 (m, 4H), 5.80 (s, 2H). LCMS: No molecular ion was detected. Evaluation of pesticide activity
[0147] As previously discussed, the compounds disclosed herein exhibit different pesticide activities. For example, the pesticide activity may include herbicidal activity. The following Table 3 illustrates the selective herbicidal activity of some compounds against various weeds and crops.
[0148] For the results exemplified in Table 3, Table 2 below lists the growth stages of the plants at the time of application: Table 2: Plant growth stage at the time of application
[0149] The examples used below are technical grade and include the control 2,4-D isooctyl ester (CAS 25168-26-7), with the exception of 2,4-D choline, which is available from Corteva Agriscience LLC under the trade name ENLIST Commercially available 2,4-D choline was used. The technical grade material was first dissolved in 3 ml of a solvent mixture of 97.3% acetone: dimethyl sulfoxide (DMSO) and then diluted with 17 ml of a solvent mixture containing acetone, water, isopropanol, DMSO, Crop oil concentrate (heavy paraffinic petroleum oil and nonionic emulsifier, commercially available from Rosecare) and nonionic Tergitol 1557, these in a ratio of 40.3:45.3:11.9:1.3:1.0:0.2 v / v. The total mixing volume was 20 ml. Post-emergence application methods for herbicide evaluation
[0150] Plants were grown in a soil medium consisting of 90% by volume Promix BX (Premier Tech Horticulture, Quakertown, PA) and 10% Profile Greens Grade (Profile Products LLC, Buffalo Grove, IL). Promix BX contains approximately 83% sphagnum peat moss, 13% perlite, 5% vermiculite, and appropriate amounts of limestone, starter fertilizer, and wetting agent. Profile Greens Grade is a sand-grade granule formed from calcined illite and montmorillonite clays. Several seeds of each plant were planted in 10 cm2 pots and top-watered twice daily. Plant material was propagated in a warm greenhouse at Corteva's global headquarters (Indianapolis, Indiana, USA) in a temperature range of 25-28°C and a relative humidity of 50% to 60%. Supplement natural light with 1000W metal halide ceiling lamps, with an average illuminance of 500μE m -2 s -1 Photosynthetically active radiation for 16 hours per day. Plants were top watered before herbicide applications and shallowly watered after herbicide applications.
[0151] Weigh the appropriate amount of test material in its industrial form into a glass vial to provide 280 or 560 g acid equivalent (ae) / ha. Dissolve the sample in 3 ml of Solvent 1. Solvent 1 is 97% acetone and 3% dimethyl sulfoxide and is used as a general purpose solvent (GPS) for dissolving industrial materials. If the sample does not dissolve readily, place the sample bottle in hot water and sonicate for 20 minutes. This usually results in complete dissolution of the test material. The sample is then diluted to its final concentration using 17 ml of Solvent 2 for a total of 20 ml of spray solution. Solvent 2 contains acetone, water, isopropanol, DMSO, Crop oil concentrate (heavy paraffinic petroleum and nonionic emulsifier, commercially available from Rosecare) and nonionic Tergitol 1557, these in a 40.3:45.3:11.9:1.3:1.0:0.2 v / v ratio. All percentages are listed on a volume basis. 2,4-D choline, such as available from Corteva Agriscience LLC under the trade name ENLIST Commercially available 2,4-D choline was applied and diluted with solvent 2 to compare all materials in the same spray solution.
[0152] According to species, 2 repetitions of herbicide application were carried out to each plant species at 4 to 8 leaf stages. Processed with a calibrated research crawler sprayer (by De Vries Manufacturing, Hollandale, MN, USA, USA) of Hollandale, Minnesota, USA, the III generation research sprayer) to provide a spray volume of 187L / ha. The crawler sprayer was equipped with the 8003E nozzle of Spray Systems Company (North Avenue and Schmale Road, PO Box 7900, Wheaton, IL 60187), and used a spray pressure of 276kPa pressure and a speed of 3.1km / h. The nozzle height was 46cm higher than the plant canopy. The experimental design for the test was a random complete block, and each treatment was repeated 2 times. After application, according to randomization, plants were placed on carts and put back in the greenhouse. After treatment with Indianapolis city water, plants were shallowly watered or fertilized three times a week with a commercial fertilizer solution (Jack's Professional 15-5-15 4Ca 2Mg fertilizer (manufactured by JRPETERS INC., 6656 Grant Way, Allentown, PA 18106, www.jrpeters.com). Visual percent control ratings were made on a scale of 0% to 100% (where 0 is no control and 100 is complete plant death) at 7, 14, and 21 days after treatment. The effects of representative experimental compounds on the growth of western amaranth were measured.
[0153] Following the methods outlined above in the post-emergence application method for herbicide evaluation, the effects of representative test compounds on the growth of western amaranth (AMATA) (common name: high water hemp) were determined at 2 different levels (280 and 560 g acid equivalent (ae) / ha, respectively) of the test test active. Plants were treated with one of these compounds and control plants were not treated. Twenty-one days after treatment, the plants were measured. The data are expressed as a percentage reduction in plant size relative to the untreated control. Now referring to Table 3, some of the tested compounds showed a significant effect on the growth of this common weed species. Measuring the effects of representative experimental compounds on ragweed growth
[0154] According to the method outlined above in the post-emergence application method for herbicide evaluation, under 2 different levels (respectively 280 and 560g acid equivalent (ae) / ha) of the test experimental active substance, the influence of representative experimental compounds on the growth of ragweed (AMBEL) (common ragweed) was determined. The plants were treated with one of these compounds and the control plants were not treated. Twenty-one days after the treatment, the plants were measured. The data are represented by a percentage reduction of plant size relative to the untreated control. Now with reference to Table 4, some of the tested compounds show a significant impact on the growth of this common weed species. Measuring the effects of representative experimental compounds on the growth of Abutilon
[0155] Following the methods outlined above in the post-emergence application method for herbicide evaluation, the effects of representative experimental compounds on the growth of Abutilon (ABUTH) (common name: velvet leaf) were determined at 2 different levels (280 and 560 g acid equivalent (ae) / ha, respectively) of the test experimental active substance. Plants were treated with one of these compounds and control plants were not treated. Twenty-one days after treatment, the plants were measured. The data are expressed as a percentage reduction in plant size relative to the untreated control. Now referring to Table 3, some of the tested compounds show a significant effect on the growth of this common weed species. Measuring the effects of representative experimental compounds on Chenopodium album growth
[0156] Following the methods outlined above in the post-emergence application method for herbicide evaluation, the effects of representative test compounds on the growth of Chenopodium album (CHEAL) (common name: common gray grass) were determined at 2 different levels (280 and 560 g acid equivalent (ae) / ha, respectively) of the test test active. Plants were treated with one of these compounds and control plants were not treated. Twenty-one days after treatment, the plants were measured. The data are expressed as a percentage reduction in plant size relative to the untreated control. Referring now to Table 3, some of the tested compounds showed a significant effect on the growth of this common weed species. Measuring the effects of representative experimental compounds on the growth of Erigeron canadensis
[0157] Following the methods outlined above in the post-emergence application method for herbicide evaluation, the effects of representative experimental compounds on the growth of ERICA (common name: Erigeron canadensis) were determined at 2 different levels (280 and 560 g acid equivalent (ae) / ha, respectively) of the test experimental active material. Plants were treated with one of these compounds and control plants were not treated. Twenty-one days after treatment, the plants were measured. The data are expressed as a percentage reduction in plant size relative to the untreated control. Now referring to Table 3, some of the tested compounds show a significant effect on the growth of this common weed species. Measuring the effects of representative experimental compounds on soybean growth
[0158] The performance of representative test compounds on soybean (available from Corteva Pharmaceutical Industries, Inc., MD, USA) was determined at 2 different levels (280 and 560 g ae / ha, respectively) of the test active material following the procedures outlined above in the post-emergence application method for herbicide evaluation. Commercially available The effects of these compounds on the growth of soybean (soybean) were studied. Plants were treated with one of these compounds and control plants were not treated. Twenty-one days after treatment, the plants were measured. Data are expressed as a percentage reduction in plant size relative to the untreated control. Table 3: Average effects of representative compounds on the growth of exemplary plants Volatility of compounds measured by thermogravimetric analysis (TGA)
[0159] In short, the weight loss rate measured in μg / min can be used to determine the vapor pressure as shown in the following simplified equation: Where k is the intrinsic volatility and A is the surface area,
[0160] Reference is now made to Figure 2. A plot of the weight loss of a solid sample as a function of time produces a linear curve; the slope of the curve is the weight loss rate. When the method is used to measure the volatility of an aqueous salt concentrate or a liquid concentrate, water or acetone present in the sample volatilizes before the sample of interest. The first linear loss region of the curve is the loss of water or acetone, and the second linear region is characteristic of the sample of interest.
[0161] To illustrate the volatility differences between some of the compounds disclosed herein and the widely used 2,4-D, data from both 2,4-D choline and exemplary compounds of the present disclosure are presented in Table 4 below. Table 4: Volatility data measured by TGA Safe composition
[0162] The safener composition comprising the compound according to Formula I may be mixed or applied in combination with (b) a carboxylic acid azole safener or an agriculturally acceptable salt or ester thereof.
[0163] In some aspects, (a) and (b) are used in an amount sufficient to induce unexpectedly enhanced herbicidal effects (e.g., increased damage or injury to undesirable vegetation) while still showing good crop compatibility (e.g., no increase in damage to crops or minimal increase in damage or injury to crops) compared to the application of the herbicidal compound (a) or (b) alone. In some aspects, the damage or injury to undesirable vegetation caused by the safe compositions and methods disclosed herein is evaluated using a scale of 0% to 100% compared to untreated control vegetation, wherein 0% indicates no damage to undesirable vegetation and 100% indicates complete destruction of undesirable vegetation. Similarly, in some aspects, the damage or injury to crops caused by the safe compositions and methods disclosed herein is evaluated using a scale from 0% to 100% when compared to control crops treated with herbicides or safeners alone, wherein 0% indicates no damage to crops and 100% indicates complete destruction of crops.
[0164] In some aspects, the combined action of (a) a compound according to formula I and (b) a carboxylic acid azole safener or its agriculturally acceptable salt or ester results in an unexpected enhancement of the herbicidal effect on undesirable vegetation, even at an application rate lower than those herbicides that typically have herbicidal effects by themselves. In some aspects, the compositions and methods disclosed herein can be used based on the individual components at a lower application rate to achieve a herbicidal effect comparable to the effect produced by the individual components at a normal application rate. In some aspects, the combined action of (a) a compound according to formula I and (b) a carboxylic acid azole safener or its agriculturally acceptable salt or ester results in an unexpected protection of the desired crop from the damage that the individual herbicides may cause to the crop.
[0165] In some aspects, the weight ratio of (a) a compound according to Formula I (in g ae / ha) to (b) a carboxylic acid azole safener or an agriculturally acceptable salt or ester thereof (in g ai / ha) can be 1:5 or greater, such as 1:4.75 or greater, 1:4.5 or greater, 1:4.25 or greater, 1:4 or greater, 1:3.75 or greater, 1:3.5 or greater, 1:3.25 or greater, 1:3 or greater, 1:2.75 or greater, 1:2.5 or greater, 1:2.25 or greater, 1:2 or greater, 1:1.9 or greater, 1:1.8 or greater, 1:1.7 or greater, 1:1.6 or greater, 1:1.5 or greater, 1:1.4 or greater, 1:1.3 or greater, 1:1.2 or greater, 1:1.1 or greater, 1:1. 1 or more, 1.2:1 or more, 1.3:1 or more, 1.4:1 or more, 1.5:1 or more, 1.6:1 or more, 1.7:1 or more, 1.8:1 or more, 1.9:1 or more, 2:1 or more, 2.25:1 or more, 2.5:1 or more, 2.75:1 or more, 3:1 or more, 3.25:1 or more, 3.5:1 or more, 3.75:1 or more, 4:1 or more, 4.25:1 or more, 4.5:1 or more, 4.75:1 or more, or 5:1 or more; the weight ratio of (a) to (b) may be 5:1 or less, such as 4.75:1 or less, 4.5:1 or less, , 4.25:1 or less, 4:1 or less, 3.75:1 or less, 3.5:1 or less, 3.25:1 or less, 3:1 or less, 2.75:1 or less, 2.5:1 or less, 2.25:1 or less, 2:1 or less, 1.9:1 or less, 1.8:1 or less, 1.7:1 or less, 1.6:1 or less, 1.5:1 or less, 1.4:1 or less, 1.3:1 or less, 1.2:1 or less, 1.1:1 or less, 1:1 or less, 1:1.1 or less, 1:1.2 or less, 1:1.3 or less, 1:1.4 or less, 1:1.5 or less, 1:1. 6 or less, 1:1.7 or less, 1:1.8 or less, 1:1.9 or less, 1:2 or less, 1:2.25 or less, 1:2.5 or less, 1:2.75 or less, 1:3 or less, 1:3.25 or less, 1:3.5 or less, 1:3.75 or less, 1:4 or less, 1:4.25 or less, 1:4.5 or less, or 1:4.75 or less; or the weight ratio of (a) to (b) can range from any minimum ratio to any maximum ratio provided above, such as 1:5 to 5:1, 1:2 to 5:1, 1:1 to 3:1, 1:3 to 4:1, or 1:1.5 to 3.5:1.
[0166] In some aspects, (a) and (b) can be used independently at a purity of 90% to 100% (eg, 95% to 100%) according to nuclear magnetic resonance (NMR) spectroscopy. Carboxylic Acid Azoles Safener
[0167] In addition to compounds according to formula I, the compositions and methods of the present disclosure may also include carboxylic acid azole safeners or their agriculturally acceptable salts or esters. Herbicide safeners are molecules used in combination with herbicides to make them "safer", i.e., reduce the weeding effect of herbicides on crops and improve the selectivity between crops and the undesirable vegetation targeted by herbicides. Herbicide safeners can be used to pre-treat crop seeds before planting. Herbicide safeners can also be sprayed on plants in a mixture with herbicides or separately or sequentially with herbicides.
[0168] Azoles are a class of five-membered nitrogen heterocyclic compounds that contain at least one additional heteroatom (eg, nitrogen, sulfur, or oxygen) within the heterocyclic ring. Examples of azoles include, for example, pyrazole, imidazole, thiazole, oxazole, isoxazole, and triazole.
[0169] Carboxylic acid azole safener is a class of safeners based on the azole part substituted by carboxylic acid ester. The example of carboxylic acid azole safener includes carboxylic acid pyrazole safener, carboxylic acid imidazole safener, carboxylic acid thiazole safener, carboxylic acid oxazole safener, carboxylic acid isoxazole safener and carboxylic acid triazole safener. In some aspects, the composition may include a carboxylic acid azole safener selected from the group consisting of: fenthiocarb, fenthiocarb, fenthiocarb, isoxadiazole, pyrazole oxalate, its agriculturally acceptable salt or ester or a combination thereof. In some aspects, the carboxylic acid azole safener may include fenthiocarb ethyl, isoxadiazole ethyl, pyrazole oxalate diethyl or a combination thereof.
[0170] In some aspects, the carboxylic acid azole safener may include fenthiocarbamide as shown below, or an agriculturally acceptable salt or ester thereof. The safening activity of fenthiocarbamide is described in The Pesticide Manual, 18th Edition, 2016.
[0171] In some aspects, fenthiocarb is provided in the form of an agriculturally acceptable salt or ester. An exemplary agriculturally acceptable fenthiocarb is fenthiocarb ethyl ester as shown below.
[0172] In some aspects, the carboxylic acid azole safener may include chloranil as shown below, or an agriculturally acceptable salt or ester thereof. The safening activity of chloranil is described in The Pesticide Manual, 18th Edition, 2016.
[0173] In some aspects, the carboxylic acid azole safener may include oxadiazole as shown below, or an agriculturally acceptable salt or ester thereof. The safening activity of oxadiazole is described in The Pesticide Manual, 18th Edition, 2016.
[0174] In some aspects, the carboxylic acid azole safener may include isoxadifen as shown below, or an agriculturally acceptable salt or ester thereof. The safening activity of isoxadifen is described in The Pesticide Manual, 18th Edition, 2016.
[0175] In some aspects, isoxadifen is provided in the form of an agriculturally acceptable salt or ester. An exemplary agriculturally acceptable ester of isoxadifen as shown below is isoxadifen ethyl.
[0176] In some aspects, the carboxylic acid azole safener can include pyrazolyl oxalate as shown below, or an agriculturally acceptable salt or ester thereof. The safening activity of pyrazolyl oxalate is described in The Pesticide Manual, 18th Edition, 2016.
[0177] In some aspects, pyrazolyl oxalate is provided in the form of an agriculturally acceptable salt or ester. An exemplary agriculturally acceptable ester of pyrazolyl oxalate, shown below, is diethyl pyrazolyl oxalate.
[0178] Carboxylic acid azole safeners include, for example, isoxadifen and agriculturally acceptable salts and esters thereof. Isoxadifen has the following chemical structure. This form of isoxadifen may also be referred to as "isoxadifen-acid".
[0179] In some aspects, the safener can include isoxadifen, an agriculturally acceptable salt of isoxadifen, an agriculturally acceptable ester of isoxadifen, or a mixture thereof. An exemplary agriculturally acceptable ester of isoxadifen, as shown below, is isoxadifen ethyl.
[0180] In some aspects, carboxylic acid azole safeners can be provided in the form of agriculturally acceptable esters. Suitable esters include, but are not limited to, methyl esters, ethyl esters, isopropyl esters, butyl esters, hexyl esters, heptyl esters, isoheptyl esters, methyl hexyl esters, isooctyl esters, 2-ethylhexyl esters, and butoxyethyl esters, and aryl esters such as benzyl esters. Exemplary agriculturally acceptable esters of carboxylic acid azole safeners described herein include methyl esters, ethyl esters, and diethyl esters.
[0181] In some aspects, the carboxylic acid azole safener may comprise an agriculturally acceptable salt of the carboxylic acid azole safener. The agriculturally acceptable salt of the carboxylic acid azole safener includes, for example, sodium, potassium, ammonium, monoethanolammonium, diethanolammonium, triethanolammonium, monoisopropanolammonium, diisopropanolammonium, triisopropanolammonium, choline, N,N-dimethylethanolammonium, diethylammonium, dimethylammonium, trimethylammonium, triethylammonium and isopropylammonium salts of the carboxylic acid azole safener.
[0182] The carboxylic acid azole safeners, when applied in combination with herbicides, can reduce phytotoxicity to crops such as wheat, barley, triticale, rye, teff, oats, maize, sorghum, millet, rice, millet, canola / rape, flax, soybean, sunflower, sugar beet, cotton, sugar cane, and forage grasses.
[0183] The carboxylic acid azole safener or its agriculturally acceptable salt or ester may be used in an amount sufficient to induce a safening effect. In some aspects, the carboxylic acid azole safener is selected from the group consisting of fenthiocarb, fenthiocarb, fenthiocarb, fenthiocarb, isoxadiazole, pyraclostrobin, an agriculturally acceptable salt or ester thereof, or a combination thereof, and is applied to vegetation or an area adjacent to vegetation or to soil or water in an amount of 1 g active ingredient per hectare (ai / ha) or more, for example 2 g ai / ha or more, 3 g ai / ha or more, 4 g ai / ha or more, 5 g ai / ha or more, 6 g ai / ha or more, 7 g ai / ha or more, 8 g ai / ha or more, 9 g ai / ha or more, 10 g ai / ha or more, 11 g ai / ha or more, 12 g ai / ha or more, 13 g ai / ha or more, 14 g ai / ha or more, 15 g ai / ha or more, 16 g ai / ha or more, 17 g ai / ha or more, 18 g ai / ha or more, 19 g ai / ha or more. g ai / ha or more, 20g ai / ha or more, 22g ai / ha or more, 24g ai / ha or more, 25g ai / ha or more, 26g ai / ha or more, 28g ai / ha or more, 30g ai / ha or more, 32g ai / ha or more, 34g ai / ha or more, 35g ai / ha or more, 36g ai / ha or more, 38g ai / ha or more, 40g ai / ha or more, 42.5g ai / ha or more, 45g ai / ha or more, 47.5g ai / ha or more, 50g ai / ha or more, 52.5g ai / ha or more, 55g ai / ha or more, 57.5g ai / ha or more5g ai / ha or more, 60g ai / ha or more, 65g ai / ha or more, 70g ai / ha or more, 75g ai / ha or more, 80g ai / ha or more, 85g ai / ha or more, 90g ai / ha or more, 95g ai / ha or more, 100g ai / ha or more, 110g ai / ha or more, 120g ai / ha or more, 130g ai / ha or more, 140g ai / ha or more, 150g ai / ha or more, 160g ai / ha or more, 170g ai / ha or more, 180g ai / ha or more, 190g ai / ha or more, 200g ai / ha or more, 210g ai / ha or more, 220g ai / ha or more, 230g ai / ha or more, 240g ai / ha or more, 250g ai / ha or more, 260g ai / ha or more g ai / ha or less, 190 g ai / ha or less, 180 g ai / ha or less, 170 g ai / ha or less, 160 g ai / ha or less, 150 g ai / ha or less, 140 g ai / ha or less, 130 g ai / ha or less, 120 g ai / ha or less, 140 g ai / ha or less, 150 g ai / ha or less, 160 g ai / ha or less, 170 g ai / ha or less, 180 g ai / ha or less, 190 g ai / ha or less, 180 g ai / ha or less, 180 g ai / ha or less, 190 g ai / ha or less, 190 g ai / ha or less, 18 ... ai / ha or less, 110g ai / ha or less, 100g ai / ha or less, 95g ai / ha or less, 90g ai / ha or less, 85g ai / ha or less, 80g ai / ha or less, 75g ai / ha or less, 70g ai / ha or less, 65g ai / ha or less, 60g ai / ha or less, 57.5g ai / ha or less, 55g ai / ha or less, 52.5g ai / ha or less, 50g ai / ha or less, 47.5g ai / ha or less, 45g ai / ha or less, 42.5g ai / ha or less, 40g ai / ha or less, 38g ai / ha or less, 36g ai / ha or less, 35g ai / ha or less, 34g ai / ha or less, 32g ai / ha or less, 30g ai / ha or less, 28g ai / ha or less, 26g ai / ha or less, 25g ai / ha or less, 24g ai / ha or less, 22g ai / ha or less, 20g ai / ha or less, 19g ai / ha or less, 18g ai / ha or less, 17g ai / ha or less, 16g ai / ha or less, 15g ai / ha or less, 14g ai / ha or less, 13g ai / ha or less, 12g ai / ha or less, 11g ai / ha or less, 10g ai / ha or less, 9g ai / ha or less ai / ha or less, 8g ai / ha or less, 7g ai / ha or less, 6g ai / ha or less, 5g ai / ha or less, 4g ai / ha or less, 3g ai / ha or less, or 2g ai / ha or less; or an amount in any range defined between any pair of the foregoing values, such as 1g ai / ha to 300g ai / ha, 5g ai / ha to 150g ai / ha, 10g ai / ha to 200g ai / ha, 20g ai / ha to 75g ai / ha, or 40g ai / ha to 100g ai / ha. . Preparations
[0184] The present disclosure also includes formulations and methods of the compositions disclosed herein. additive
[0185] The compositions and methods disclosed herein can also be mixed with additives or applied together with additives. In some aspects, additives are added in sequence. In some aspects, additives are added simultaneously. In some aspects, additives are premixed with compounds according to Formula I. In some aspects, additives are premixed with carboxylic acid azole safeners or their agriculturally acceptable salts or esters. Other pesticides
[0186] Some aspects of the disclosed safening compositions include adding one or more additional pesticide active ingredients to the safening compositions. These pesticide active ingredients may include one or more herbicides, insecticides, fungicides, nematicides, miticides, arthropodicides, bactericides, plant growth regulators, or combinations thereof that are compatible with the compositions of the present disclosure.
[0187] In some aspects, the additive is an additional herbicide. For example, the compositions described herein can be co-applied with one or more additional herbicides to control undesirable vegetation. The compositions can be formulated with one or more additional herbicides, tank-mixed with one or more additional herbicides, or applied sequentially with one or more additional herbicides, such as the exemplary herbicides described below. ALS inhibitors
[0188] In addition to the compound according to formula I, the composition may also include an acetolactate synthase (ALS) inhibitor. ALS inhibitors destroy the production of amino acids in plants, which ultimately leads to inhibition of DNA synthesis. Examples of ALS inhibitors include sulfonylureas, imidazolinones, triazolopyrimidine sulfonamides, pyrimidinyloxybenzoates, and sulfonylaminocarbonyltriazolinones. In some aspects, the ALS inhibitor may contain a triazolopyrimidine sulfonamide herbicide. In some aspects, the ALS inhibitor may contain an imidazolinone herbicide. In some aspects, the ALS inhibitor may contain a pyrimidinyloxybenzoate herbicide. In some aspects, the ALS inhibitor may contain a sulfonylaminocarbonyltriazolinone herbicide. In some aspects, the ALS inhibitor may contain a sulfonylurea herbicide.
[0189] In some aspects, the composition may include an ALS inhibitor selected from the group consisting of imidazolinone, triazolopyrimidine sulfonamide, pyrimidinyloxybenzoate, sulfonylaminocarbonyl triazolinone, sulfonylurea, and combinations thereof. In some cases, the composition may include amidosulfuron, tetrazosulfuron, bispyribac-sodium, benzylsulfuron, chlorimuron, chlorsulfuron, ethoxysulfuron, fluazifop-methyl ... Disulfuron-methyl, bis-ether clopyrasulfuron-methyl, sulfamethoxazole, metsulfuron-methyl, nicosulfuron, pyrimidinesulfuron-methyl, epoxysulfuron-methyl, penoxsulam, primisulfuron-methyl, propansulfuron-methyl, propazinesulfuron-methyl, trifloxysulfuron-methyl, pyrazosulfuron-methyl, pyrimidinesulfuron-methyl, pyrimidinesulfuron-methyl, pyrimidinesulfuron-methyl, pyrimidinesulfuron-methyl, pyrimidinesulfuron-methyl, sulfamethoxazole, sulfamethoxazole, thiasulfuron-methyl, thifensulfuron-methyl, ether bensulfuron-methyl, bensulfuron-methyl, trifloxysulfuron-methyl, flufenac, trifloxysulfuron-methyl, their agriculturally acceptable salts and esters, and combinations thereof.
[0190] The ALS inhibitor or an agriculturally acceptable salt or ester thereof may be applied to vegetation or areas adjacent to vegetation or to soil or water in an amount sufficient to induce a herbicidal effect to prevent the emergence or growth of vegetation. In some aspects, the ALS inhibitor or an agriculturally acceptable salt or ester thereof is applied to vegetation or an area adjacent to vegetation or to soil or water in an amount of 0.25 grams of active ingredient per hectare (g ai / ha) or more, such as 0.3 g ai / ha or more, 0.4 g ai / ha or more, 0.5 g ai / ha or more, 0.6 g ai / ha or more, 0.7 g ai / ha or more, 0.8 g ai / ha or more, 0.9 g ai / ha or more, 1 g ai / ha or more, 1.5 g ai / ha or more, 2 g ai / ha or more, 2.5 g ai / ha or more, 3 g ai / ha or more, 3.5 g ai / ha or more, 4 g ai / ha or more, 4.5 g ai / ha or more, 5 g ai / ha or more, 6 g ai / ha or more, 7 g ai / ha or more, 8 g ai / ha or more, 9 g ai / ha or more, 10 g ai / ha or more. g ai / ha or more, 15g ai / ha or more, 20g ai / ha or more, 25g ai / ha or more, 30g ai / ha or more, 35g ai / ha or more, 40g ai / ha or more, 45g ai / ha or more, 50g ai / ha or more, 55g ai / ha or more, 60g ai / ha or more, 65g ai / ha or more, 70g ai / ha or more, 75g ai / ha or more, 80g ai / ha or more, 85g ai / ha or more, 90g ai / ha or more, 95g ai / ha or more, 100g ai / ha or more, 110g ai / ha or more, 120g ai / ha or more, 130g ai / ha or more, 140g ai / ha or more, 150g ai / ha or more, 160g ai / ha or more, 170g ai / ha or more, 180g ai / ha or more g ai / ha or more, 190g ai / ha or more, 200g ai / ha or more, 220g ai / ha or more, 240g ai / ha or more, 250g ai / ha or more, 260g ai / ha or more, 280g ai / ha or more, 300g ai / ha or more, 320g ai / ha or more, 340g ai / ha or more, 350g ai / ha or more, 360g ai / ha or more, 380g ai / ha or more, 400g ai / ha or more, 420g ai / ha or more, 440g ai / ha or more, 460g ai / ha or moreg ai / ha or more, 480g ai / ha or more, 500g ai / ha or more, 520g ai / ha or more, 540g ai / ha or more, 560g ai / ha or more, 580g ai / ha or more, 600g ai / ha or more, 625g ai / ha or more, 650g ai / ha or more, 675g ai / ha or more, 700g ai / ha or more, 725g ai / ha or more, 750g ai / ha or more, 775g ai / ha or more, 800g ai / ha or more, 825g ai / ha or more, 850g ai / ha or more, 875g ai / ha or more, 900g ai / ha or more, 925g ai / ha or more, 950g ai / ha or more, 975g ai / ha or more, 1000g ai / ha or more, 1050g ai / ha or more g ai / ha or more, 1100 g ai / ha or more, 1150 g ai / ha or more, 1200 g ai / ha or more, 1250 g ai / ha or more, 1300 g ai / ha or more, 1350 g ai / ha or more, 1400 g ai / ha or more, 1450 g ai / ha or more, 1500 g ai / ha or more, 1550 g ai / ha or more, 1600 g ai / ha or more, 1650 g ai / ha or more, 1675 g ai / ha or more, 1680 g ai / ha or more, or 1690 g ai / ha or more; in an amount of 1700 g ai / ha or less, such as 1700 g ai / ha or less, 1750 g ai / ha or less, 1750 g ai / ha or more, 1760 g ai / ha or more g ai / ha or less, 1550 g ai / ha or less, 1500 g ai / ha or less, 1450 g ai / ha or less, 1400 g ai / ha or less, 1350 g ai / ha or less, 1300 g ai / ha or less, 1250 g ai / ha or less, 1200 g ai / ha or less, 1150 g ai / ha or less, 1100 g ai / ha or less, 1050 g ai / ha or less, 1000 g ai / ha or less, 975 g ai / ha or less, 950 g ai / ha or less, 925 g ai / ha or less, 900 g ai / ha or less, 875 g ai / ha or less, 850 g ai / ha or less, 825 g ai / ha or less, 800 g ai / ha or less, 775 g ai / ha or less ai / ha or less, 750g ai / ha or less, 725g ai / ha or less, 700gg ai / ha or less, 675 g ai / ha or less, 650 g ai / ha or less, 625 g ai / ha or less, 600 g ai / ha or less, 580 g ai / ha or less, 560 g ai / ha or less, 540 g ai / ha or less, 520 g ai / ha or less, 500 g ai / ha or less, 480 g ai / ha or less, 460 g ai / ha or less, 440 g ai / ha or less, 420 g ai / ha or less, 400 g ai / ha or less, 380 g ai / ha or less, 360 g ai / ha or less, 350 g ai / ha or less, 340 g ai / ha or less, 320 g ai / ha or less, 300 g ai / ha or less, 280 g ai / ha or less, 260 g ai / ha or less g ai / ha or less, 250g ai / ha or less, 240g ai / ha or less, 220g ai / ha or less, 200g ai / ha or less, 190g ai / ha or less, 180g ai / ha or less, 170g ai / ha or less, 160g ai / ha or less, 150g ai / ha or less, 140g ai / ha or less, 130g ai / ha or less, 120g ai / ha or less, 110g ai / ha or less, 100g ai / ha or less, 95g ai / ha or less, 90g ai / ha or less, 85g ai / ha or less, 80g ai / ha or less, 75g ai / ha or less, 70g ai / ha or less, 65g ai / ha or less, 60g ai / ha or less, 55g ai / ha or less g ai / ha or less, 50g ai / ha or less, 45g ai / ha or less, 40g ai / ha or less, 35g ai / ha or less, 30g ai / ha or less, 25g ai / ha or less, 20g ai / ha or less, 15g ai / ha or less, 10g ai / ha or less, 9g ai / ha or less, 8g ai / ha or less, 7g ai / ha or less, 6g ai / ha or less, 5g ai / ha or less, 4.5g ai / ha or less, 4g ai / ha or less, 3.5g ai / ha or less, 3g ai / ha or less, 2.5g ai / ha or less, 2g ai / ha or less, 1.5g ai / ha or less, 1g ai / ha or less, 0.9g ai / ha or less, 0.8g ai / ha or less ai / ha or less, 0.7g ai / ha or less, 0.6g ai / ha or less, 0.5g ai / ha or less, 0.4g ai / ha or less, or 0.3gai / ha or less; or in an amount ranging from any of the above minimum values to any of the above maximum values, such as 0.25-1700g ai / ha, 0.25-1250g ai / ha, 0.5-150g ai / ha, 2-90g ai / ha, 2.5-200g ai / ha, 3-900g ai / ha, 5-260g ai / ha, 5-750g ai / ha, 5-1000g ai / ha, 6-280g ai / ha, 7-100g ai / ha, 10-560g ai / ha, 10-1600g ai / ha, 20-500g ai / ha, 25-140g ai / ha, 30-480g ai / ha, 40-400g ai / ha, 50-320g ai / ha ai / ha, 60-300g ai / ha, 70-1250gai / ha, 100-140g ai / ha, 140-520g ai / ha, or 250-1700g ai / ha. Triazolopyrimidine sulfonamide herbicide
[0191] In some aspects, the composition contains a herbicidally effective amount of a compound according to Formula I, and (b) bispyribac, clorac-sulam, bispyribac, fluazifop, sulfamethoxam, penoxsulam, or foramsulfuron, or an agriculturally acceptable salt or ester thereof. Bispyribac
[0192] Compositions and methods of the present disclosure may include bispyribac or an agriculturally acceptable salt or ester thereof. Bispyribac, as shown below, is a triazolopyrimidine sulfonamide that provides broad-spectrum control of many broadleaf weeds in cereals and corn. Bispyribac and methods for preparing bispyribac are known in the art. Its herbicidal activity is described, for example, in The Pesticide Manual, Sixteenth Edition, 2012.
[0193] Bispyribac may be applied to vegetation or areas adjacent to vegetation or to soil or water in an amount sufficient to induce a herbicidal action to prevent the emergence or growth of vegetation. In some aspects, florasulam is applied to vegetation or to an area adjacent to vegetation or to soil or water in an amount to prevent emergence or growth of vegetation: 0.25 g ai / ha or more, such as 0.3 g ai / ha or more, 0.4 g ai / ha or more, 0.5 g ai / ha or more, 0.6 g ai / ha or more, 0.7 g ai / ha or more, 0.8 g ai / ha or more, 0.9 g ai / ha or more, 1 g ai / ha or more, 1.1 g ai / ha or more, 1.25 g ai / ha or more, 1.5 g ai / ha or more, 1.75 g ai / ha or more, 2 g ai / ha or more, 2.25 g ai / ha or more, 2.5 g ai / ha or more, 2.75 g ai / ha or more, 3 g ai / ha or more, 3.25 g ai / ha or more, 3.5 g ai / ha or more, 3.75 g ai / ha or more. or more, 4g ai / ha or more, 4.25g ai / ha or more, 4.5g ai / ha or more, 4.75g ai / ha or more, 5g ai / ha or more, 5.25g ai / ha or more, 5.5g ai / ha or more, 5.75g ai / ha or more, 6g ai / ha or more, 6.25g ai / ha or more, 6.5g ai / ha or more, 6.75g ai / ha or more, 7g ai / ha or more, 7.25g ai / ha or more, 7.5g ai / ha or more, 8g ai / ha or more, 8.5g ai / ha or more, 9g ai / ha or more, or 9.5g ai / ha or more; in the following amounts: 10g ai / ha or less, such as 9.5g ai / ha or less, 9g ai / ha or less, 8.5g ai / ha or less, 8g ai / ha or more ai / ha or less, 7.5g ai / ha or less, 7.25g ai / ha or less, 7g ai / ha or less, 6.75g ai / ha or less, 6.5g ai / ha or less, 6.25g ai / ha or less, 6g ai / ha or less, 5.75g ai / ha or less, 5.5g ai / ha or less, 5.25g ai / ha or less, 5g ai / ha or less, 4.75g ai / ha or less, 4.5g ai / ha or less, 4.25g ai / ha or less, 4g ai / ha or less, 3.75g ai / ha or less, 3.5g ai / ha or less, 3.25g ai / ha or less, 3g ai / ha or less, 2.75 g ai / ha or less, 2.5 g ai / ha or less, 2.25 g ai / ha or less, 2 g ai / ha or less, 1.75 g ai / ha or less, 1.5 g ai / ha or less, 1.25 g ai / ha or less, 1 g ai / ha or less, 0.9 g ai / ha or less, 0.8 g ai / ha or less, 0.7 g ai / ha or less, 0.6 g ai / ha or less, 0.5 g ai / ha or less, 0.4 g ai / ha or less, or 0.3 g ai / ha or less; or in an amount ranging from any of the foregoing minimum values to any of the foregoing maximum values, such as 0.25-10 g ai / ha, 0.25-7 g ai / ha, 0.4-6.5 g ai / ha, ai / ha, 0.5-6gai / ha, 0.6-9gai / ha, 0.7-8.5g ai / ha, 0.8-4.5g ai / ha, 1-4g ai / ha, 1.1-7.5g ai / ha, 1.5-5.75g ai / ha, 2-7.25g ai / ha, 2.25-10g ai / ha, 3-8.5g ai / ha, or 3.5-9.5g ai / ha. . Clometsulfuron
[0194] The compositions and methods of the present disclosure may include clofosulphonamide or its agriculturally acceptable salt or ester. Clofosulphonamide and methods for preparing clofosulphonamide are known in the art. In some aspects, clofosulphonamide can be provided as an agriculturally acceptable ester of clofosulphonamide. Clofosulphonamide methyl ester as shown below is a triazolopyrimidine sulfonamide that provides broad-spectrum control of many broadleaf weeds in soybean and other broadleaf crops. Its herbicidal activity is described in The Pesticide Manual, the 17th edition, in 2016.
[0195] Clofenac can be applied to vegetation or areas adjacent to vegetation or to soil or water in an amount sufficient to induce herbicidal action to prevent the emergence or growth of vegetation. In some aspects, clofenac is applied to vegetation or areas adjacent to vegetation or to soil or water in an amount of 2.18 g ai / ha or more, such as 2.25 g ai / ha or more, 2.5 g ai / ha or more, 2.75 g ai / ha or more, 3 g ai / ha or more, 3.25 g ai / ha or more, 3.5 g ai / ha or more, 3.75 g ai / ha or more, 4 g ai / ha or more, 4.5g ai / ha or more, 5g ai / ha or more, 6g ai / ha or more, 7g ai / ha or more, 8g ai / ha or more, 9g ai / ha or more, 10g ai / ha or more, 12g ai / ha or more, 14g ai / ha or more, 16g ai / ha or more, 18g ai / ha or more, 20g ai / ha or more, 25g ai / ha or more, 30g ai / ha or more, 35g ai / ha or more, 36g ai / ha or more, 38g ai / ha or more, 40g ai / ha or more, 42g ai / ha or more, 44g ai / ha or more, 46g ai / ha or more, 48g ai / ha or more, 50g ai / ha or more, 51g ai / ha or more, 52g ai / ha or more, 53g ai / ha or more, 54g ai / ha or more, 55g ai / ha or more in the following amounts: 61 g ai / ha or less, such as 60 g ai / ha or less, 59 g ai / ha or less, 58 g ai / ha or less, 57 g ai / ha or less, 56 g ai / ha or less, 55 g ai / ha or less, 54 g ai / ha or less, 53 g ai / ha or less, 52 g ai / ha or less, 51 g ai / ha or less, 50 g ai / ha or less, 48 g ai / ha or less, 46 g ai / ha or less, 44 g ai / ha or less, 42 g ai / ha or less, 40 g ai / ha or less, 38 g ai / ha or less, 36 g ai / ha or less, 35 g ai / ha or less. g ai / ha or less, 30 g ai / ha or less, 25 g ai / ha or less, 20 g ai / ha or less, 18 g ai / ha or less, 16 g ai / ha or less, 14 g ai / ha or less, 12 g ai / ha or less, 10 g ai / ha or less, 9 g ai / ha or less, 8 g ai / ha or less, 7 g ai / ha or less, 6 g ai / ha or less, 5 g ai / ha or less, 4.5 g ai / ha or less, 4 g ai / ha or less, 3.75 g ai / ha or less, 3.5 g ai / ha or less, 3.25 g ai / ha or less, 3 g ai / ha or less, 2.75 g ai / ha or less, 2.5 g ai / ha or less, or 2.25 g ai / ha or less; or.
[0196] With an amount ranging from any of the above minimum values to any of the above maximum values, such as 2.18-61g ai / ha, 2.5-60g ai / ha, 2.75-44g ai / ha, 3-59g ai / ha, 3.25-60g ai / ha, 3.5-40g ai / ha, 3.75-18g ai / ha, 3.75-50g ai / ha, 4-60g ai / ha, 4-52g ai / ha, 4.25-30g ai / ha, 4.25-55g ai / ha, 4.5-51g ai / ha, or 5-38g ai / ha. Diclosulam
[0197] The compositions and methods of the present disclosure may include clorac or an agriculturally acceptable salt or ester thereof. Clorac, as shown below, is a triazolopyrimidine sulfonamide that provides broad-spectrum control of many broadleaf weeds in soybeans and peanuts. Clorac and methods for preparing clorac are known in the art. Its herbicidal activity is described in The Pesticide Manual, Seventeenth Edition, 2016.
[0198] Biclosulam may be applied to vegetation or areas adjacent to vegetation or to soil or water in an amount sufficient to induce a herbicidal action to prevent the emergence or growth of vegetation. In some aspects, clorac is applied to vegetation or to an area adjacent to vegetation or to soil or water in an amount to prevent emergence or growth of vegetation: 2.18 g ai / ha or more, such as 2.25 g ai / ha or more, 2.5 g ai / ha or more, 2.75 g ai / ha or more, 3 g ai / ha or more, 3.25 g ai / ha or more, 3.5 g ai / ha or more, 4 g ai / ha or more, 4.5 g ai / ha or more, 5 g ai / ha or more, 6 g ai / ha or more, 7 g ai / ha or more, 8 g ai / ha or more, 9 g ai / ha or more, 10 g ai / ha or more, 12 g ai / ha or more, 14 g ai / ha or more, 16 g ai / ha or more, 18 g ai / ha or more, 20 g ai / ha or more, 22 g ai / ha or more, 24 g ai / ha or more, 26 g ai / ha or more. or more, 27g ai / ha or more, 28g ai / ha or more, 29g ai / ha or more, 30g ai / ha or more, 31g ai / ha or more, 31.5g ai / ha or more, 32g ai / ha or more, 32.5g ai / ha or more, 33g ai / ha or more, 33.5g ai / ha or more, 34g ai / ha or more, 34.5g ai / ha or more, or 34.75g ai / ha or more; in the following amounts: 35g ai / ha or less, such as 34.5g ai / ha or less, 34g ai / ha or less, 33.5g ai / ha or less, 33g ai / ha or less, 32.5g ai / ha or less, 32.5g ai / ha or less, 31.5g ai / ha or less, 30g ai / ha or more g ai / ha or less, 29g ai / ha or less, 28g ai / ha or less, 27g ai / ha or less, 26g ai / ha or less, 24g ai / ha or less, 22g ai / ha or less, 20g ai / ha or less, 18g ai / ha or less, 16g ai / ha or less, 14g ai / ha or less, 12g ai / ha or less, 10g ai / ha or less, 9g ai / ha or less, 8g ai / ha or less, 7g ai / ha or less, 6g ai / ha or less, 5g ai / ha or less, 4.5g ai / ha or less, 4g ai / ha or less, 3.5g ai / ha or less, 2.75g ai / ha or less, 2.5g ai / ha or less, 2.25g ai / ha or less; or in an amount ranging from any of the above minimum values to any of the above maximum values, such as 2.18-35g ai / ha, 2.5-34g ai / ha, 2.75-22g ai / ha, 3-29g ai / ha, 3.25-34g ai / ha, 3.25-32g ai / ha, 3.5-30g ai / ha, 3.75-27g ai / ha, 4-35g ai / ha, 4-30g ai / ha, 4.5-18g ai / ha, 4.5-33.5g ai / ha, 5-32g ai / ha, or 6-33g ai / ha. Sulfatamide
[0199] Compositions and methods of the present disclosure may include flumetsulam or an agriculturally acceptable salt or ester thereof. Flumetsulam, as shown below, is a triazolopyrimidine sulfonamide that provides control of broadleaf weeds and leafy plants in soybean, red pea, and corn. Flumetsulam and methods for preparing flumetsulam are known in the art. Its herbicidal activity is described in The Pesticide Manual, Seventeenth Edition, 2016.
[0200] Azosulfuron can be applied to vegetation or an area adjacent to vegetation or to soil or water in an amount sufficient to induce herbicidal action to prevent the emergence or growth of vegetation. In some aspects, azosulfuron is applied to vegetation or an area adjacent to vegetation or to soil or water in an amount of 2.18 g ai / ha or more, such as 2.5 g ai / ha or more, 2.75 g ai / ha or more, 3 g ai / ha or more, 3.5 g ai / ha or more, 4 g ai / ha or more, 4.5g ai / ha or more, 5g ai / ha or more, 7g ai / ha or more, 9g ai / ha or more, 10g ai / ha or more, 15g ai / ha or more, 20g ai / ha or more, 25g ai / ha or more, 30g ai / ha or more, 35g ai / ha or more, 36g ai / ha or more, 37g ai / ha or more, 38g ai / ha or more, 39g ai / ha or more, 40g ai / ha or more, 41g ai / ha or more, 42g ai / ha or more, 44g ai / ha or more, 46g ai / ha or more, 48g ai / ha or more, 50g ai / ha or more, 52g ai / ha or more, 54g ai / ha or more, 56g ai / ha or more, 58g ai / ha or more, 60g ai / ha or more, 62g ai / ha or more, 64g ai / ha or more g ai / ha or more, 66g ai / ha or more, 68g ai / ha or more, 70g ai / ha or more, 72g ai / ha or more, 74g ai / ha or more, or 77g ai / ha or more; in the following amounts: 78g ai / ha or less, such as 77g ai / ha or less, 75g ai / ha or less, 74g ai / ha or less, 72g ai / ha or less, 70g ai / ha or less, 68g ai / ha or less, 66g ai / ha or less, 64g ai / ha or less, 62g ai / ha or less, 60g ai / ha or less, 58g ai / ha or less, 56g ai / ha or less, 54g ai / ha or less, 52g ai / ha or less, 50g ai / ha or less, 48g ai / ha or less. g ai / ha or less, 46g ai / ha or less, 44g ai / ha or less, 42g ai / ha or less, 41g ai / ha or less, 40g ai / ha or less, 39g ai / ha or less, 38g ai / ha or less, 37g ai / ha or less, 36g ai / ha or less, 35g ai / ha or less, 30g ai / ha or less, 25g ai / ha or less, 20g ai / ha or less, 15g ai / ha or less, 10g ai / ha or less, 9g ai / ha or less, 7g ai / ha or less, 5g ai / ha or less, 4.5g ai / ha or less, 4g ai / ha or less, 3.5g ai / ha or less, 3g ai / ha or less, 2.75g ai / ha or less, 2.5g ai / ha or less; or in an amount ranging from any of the above minimum values to any of the above maximum values, such as 2.18-78g ai / ha, 2.5-75g ai / ha, 2.75-54g ai / ha, 3-46g ai / ha, 3-78g ai / ha, 3.5-39g ai / ha, 3.5-72g ai / ha, 4-60g ai / ha, 4-75g ai / ha, 4.5-25g ai / ha, 4.5-66g ai / ha, 5-58g ai / ha, or 9-62g ai / ha. Penoxsulam
[0201] Compositions and methods of the present disclosure may include penoxsulam or an agriculturally acceptable salt or ester thereof. Penoxsulam, as shown below, is a triazolopyrimidine sulfonamide that provides control of many broadleaf weeds, sedge weeds, and aquatic weeds in Echinochloa species and rice. Penoxsulam and methods for preparing penoxsulam are known in the art. Its herbicidal activity is described in The Pesticide Manual, Seventeenth Edition, 2016.
[0202] Penoxsulam may be applied to vegetation or areas adjacent to vegetation or to soil or water in an amount sufficient to induce a herbicidal action to prevent the emergence or growth of vegetation. In some aspects, penoxsulam is applied to vegetation or to an area adjacent to vegetation or to soil or water in an amount to prevent emergence or growth of vegetation: 2.5 g ai / ha or more, such as 2.75 g ai / ha or more, 3 g ai / ha or more, 3.5 g ai / ha or more, 4 g ai / ha or more, 4.5 g ai / ha or more, 5 g ai / ha or more, 6 g ai / ha or more, 7 g ai / ha or more, 8 g ai / ha or more, 9 g ai / ha or more, 10 g ai / ha or more, 12 g ai / ha or more, 14 g ai / ha or more, 16 g ai / ha or more, 18 g ai / ha or more, 20 g ai / ha or more, 22 g ai / ha or more, 24 g ai / ha or more, 26 g ai / ha or more, 28 g ai / ha or more, 30 g ai / ha or more, 32 g ai / ha or more, 34 g ai / ha or more. or more, 36g ai / ha or more, 38g ai / ha or more, 40g ai / ha or more, 41g ai / ha or more, 42g ai / ha or more, 43g ai / ha or more, 44g ai / ha or more, 45g ai / ha or more, 46g ai / ha or more, 47g ai / ha or more, 48g ai / ha or more, or 49g ai / ha or more; in the following amounts: 50g ai / ha or less, such as 49g ai / ha or less, 48g ai / ha or less, 47g ai / ha or less, 46g ai / ha or less, 45g ai / ha or less, 44g ai / ha or less, 46g ai / ha or less, 47g ai / ha or less, 48g ai / ha or more, or 49g ai / ha or more. ai / ha or less, 34g ai / ha or less, 32g ai / ha or less, 30g ai / ha or less, 28g ai / ha or less, 26g ai / ha or less, 24g ai / ha or less, 22g ai / ha or less, 20g ai / ha or less, 18g ai / ha or less, 16g ai / ha or less, 14g ai / ha or less, 12g ai / ha or less, 10g ai / ha or less, 9g ai / ha or less, 8g ai / ha or less, 7g ai / ha or less, 6g ai / ha or less, 5g ai / ha or less, 4.75g ai / ha or less, 4.5g ai / ha or less, 4.25g ai / ha or less, 4g ai / ha or less, 3.5g ai / ha or less, 3g ai / ha or less, or 2.75g ai / ha or less; or in an amount ranging from any of the above minimum values to any of the above maximum values, such as 2.5-50g ai / ha, 3-28g ai / ha, 3.5-40g ai / ha, 4-34g ai / ha, 4.25-50gai / ha, 4.5-47g ai / ha, 5-45g ai / ha, 6-36g ai / ha, 8-22g ai / ha, or 10-49g ai / ha. Formosan Sulfate
[0203] Compositions and methods of the present disclosure may include formosan or an agriculturally acceptable salt or ester thereof. Formosan, as shown below, is a triazolopyrimidine sulfonamide that provides broad-spectrum post-emergence annual grass weeds and broadleaf weed control in cereals. Formosan and methods for preparing formosan are known in the art. Its herbicidal activity is described in The Pesticide Manual, Seventeenth Edition, 2016.
[0204] Formosulam may be applied to vegetation or areas adjacent to vegetation or to soil or water in an amount sufficient to induce a herbicidal effect to prevent the emergence or growth of vegetation. In some aspects, formosan is applied to vegetation or an area adjacent to vegetation or to soil or water in an amount of 1.9 g ai / ha or more, such as 2 g ai / ha or more, 2.25 g ai / ha or more, 2.5 g ai / ha or more, 2.75 g ai / ha or more, 3 g ai / ha or more, 3.25 g ai / ha or more, 3.5 g ai / ha or more, 3.75 g ai / ha or more, 4 g ai / ha or more, 4.5 g ai / ha or more, 5 g ai / ha or more, 6 g ai / ha or more, 7 g ai / ha or more, 8 g ai / ha or more, 9 g ai / ha or more, 9.5 g ai / ha or more, 10 g ai / ha or more, 10.5 g ai / ha or more, 11 g ai / ha or more, 11.5 g ai / ha or more, 12 g ai / ha or more. g ai / ha or more, 12.5 g ai / ha or more, 13 g ai / ha or more, 13.5 g ai / ha or more, 14 g ai / ha or more, 14.5 g ai / ha or more, 15 g ai / ha or more, 15.25 g ai / ha or more, 15.5 g ai / ha or more, 15.75 g ai / ha or more, 16 g ai / ha or more, 16.25 g ai / ha or more, 16.5 g ai / ha or more, 16.75 g ai / ha or more, 17 g ai / ha or more, 17.25 g ai / ha or more, 17.5 g ai / ha or more, 17.75 g ai / ha or more, 18 g ai / ha or more, 18.25 g ai / ha or more, or 18.5 g ai / ha; in amounts such as 18.75 g ai / ha or less, such as 18.5 g ai / ha or more ai / ha or less, 18.25g ai / ha or less, 18g ai / ha or less, 17.75g ai / ha or less, 17.5g ai / ha or less, 17.25g ai / ha or less, 17gai / ha or less, 16.75g ai / ha or less, 16.5g ai / ha or less, 16.25g ai / ha or less, 16g ai / ha or less, 15.75g ai / ha or less, 15.5g ai / ha or less, 15.25g ai / ha or less, 15g ai / ha or less, 14.5g ai / ha or less, 14g ai / ha or less, 13.5g ai / ha or less, 13g ai / ha or less, 12.5 g ai / ha or less, 12 g ai / ha or less, 11.5 g ai / ha or less, 11 g ai / ha or less, 10.5 g ai / ha or less, 10 g ai / ha or less, 9.5 g ai / ha or less, 9 g ai / ha or less, 8 g ai / ha or less, 7 g ai / ha or less, 6 g ai / ha or less, 5 g ai / ha or less, 4.5 g ai / ha or less, 4 g ai / ha or less, 3.5 g ai / ha or less, 3.25 g ai / ha or less, 3 g ai / ha or less, 2.75 g ai / ha or less, 2.5 g ai / ha or less, or 2.25 g ai / ha or an amount ranging from any of the foregoing minimum values to any of the foregoing maximum values, such as 1.9-18.75 g ai / ha, 2.25-18g ai / ha, 2.5-14.5g ai / ha, 2.75-12.5g ai / ha, 2.75-18.5g ai / ha, 3-13g ai / ha, 3.25-10.5gai / ha, 3.5-16g ai / ha, 4-15.25g ai / ha, 5-18g ai / ha, 6-17.75g ai / ha, 8-16g ai / ha, 9-18g ai / ha, or 10-14.5g ai / ha. . Imidazolinone herbicides
[0205] In some aspects, the composition contains a herbicidally effective amount of a compound according to Formula I, and (b) imazapic, imazapic, methyl imazapic, imazapic, imazapic, imazapic, imazethapyr, imazethapyr, or agriculturally acceptable salts or esters thereof, or combinations thereof. Imazamox
[0206] Compositions and methods of the present disclosure may include imazamethoxam or an agriculturally acceptable salt or ester thereof. Imazamethoxam, as shown below, is a mixture of isomers and imidazolinones that provide post-emergence control of Avena species, Alopecurus australis, Apiraea, and dicotyledonous weeds in wheat, barley, rye, and sunflower. Imazamethoxam and methods for preparing imazamethoxam are known in the art. Its herbicidal activity is described in The Pesticide Manual, Seventeenth Edition, 2016.
[0207] Imazapoxetine may be applied to vegetation or areas adjacent to vegetation or to soil or water in an amount sufficient to induce a herbicidal action to prevent the emergence or growth of vegetation. In some aspects, imazamethac is applied to vegetation or an area adjacent to vegetation or to soil or water in an amount of 50 g ai / ha or more, such as 55 g ai / ha or more, 60 g ai / ha or more, 65 g ai / ha or more, 70 g ai / ha or more, 75 g ai / ha or more, 80 g ai / ha or more, 90 g ai / ha or more, 95 g ai / ha or more, 100 g ai / ha or more, 110 g ai / ha or more, 120 g ai / ha or more, 130 g ai / ha or more, 140 g ai / ha or more, 150 g ai / ha or more, 160 g ai / ha or more, 170 g ai / ha or more, 180 g ai / ha or more, 190 g ai / ha or more, 200 g ai / ha or more, 220 g ai / ha or more, 240 g ai / ha or more. g ai / ha or more, 260g ai / ha or more, 280g ai / ha or more, 300g ai / ha or more, 320g ai / ha or more, 340g ai / ha or more, 360g ai / ha or more, 380g ai / ha or more, 400g ai / ha or more, 420g ai / ha or more, 440g ai / ha or more, 460g ai / ha or more, 480g ai / ha or more, 500g ai / ha or more, 520g ai / ha or more, 540g ai / ha or more, 560g ai / ha or more, 580g ai / ha or more, 600g ai / ha or more, 620g ai / ha or more, 640g ai / ha or more, 650g ai / ha or more, 660g ai / ha or more, 670g ai / ha or more, 680g ai / ha or more ai / ha or more, or 690g ai / ha or more;In amounts such as 700 g ai / ha or less, such as 690 g ai / ha or less, 680 g ai / ha or less, 670 g ai / ha or less, 660 g ai / ha or less, 650 g ai / ha or less, 640 g ai / ha or less, 620 g ai / ha or less, 600 g ai / ha or less, 580 g ai / ha or less, 560 g ai / ha or less, 540 g ai / ha or less, 520 g ai / ha or less, 500 g ai / ha or less, 480 g ai / ha or less, 460 g ai / ha or less, 440 g ai / ha or less, 420 g ai / ha or less, 400 g ai / ha or less, 380 g ai / ha or less, 360 g ai / ha or less, 340 g ai / ha or less. g ai / ha or less, 320g ai / ha or less, 300g ai / ha or less, 280g ai / ha or less, 260g ai / ha or less, 240g ai / ha or less, 220g ai / ha or less, 200g ai / ha or less, 190g ai / ha or less, 180g ai / ha or less, 170g ai / ha or less, 160g ai / ha or less, 150g ai / ha or less, 140g ai / ha or less, 130g ai / ha or less, 120g ai / ha or less, 110g ai / ha or less, 100g ai / ha or less, 95g ai / ha or less, 90g ai / ha or less, 85g ai / ha or less, 80g ai / ha or less, 75g ai / ha or less, g ai / ha or less, 70 g ai / ha or less, 65 g ai / ha or less, 60 g ai / ha or less, or 55 g ai / ha or less; or in an amount ranging from any of the above minimum values to any of the above maximum values, such as 50-700 g ai / ha, 55-400 g ai / ha, 60-650 g ai / ha, 75-520 g ai / ha, 80-400 g ai / ha, 85-500 g ai / ha, 90-220 g ai / ha, 100-700 g ai / ha, 100-500 g ai / ha, 110-640 g ai / ha, 120-420 g ai / ha, 120-500 g ai / ha, 140-670 g ai / ha, or 150-580 g ai / ha. ; Methoxazolidinone
[0208] Compositions and methods of the present disclosure may include imazamox or an agriculturally acceptable salt or ester thereof. Imazamox, as shown below, is an imidazolinone that provides pre- and post-emergence control of broadleaf weeds and grass weeds in, for example, rice, corn, rapeseed, alfalfa, peas, and beans. Imazamox and methods of preparing imazamox are known in the art. Its herbicidal activity is described in The Pesticide Manual, Seventeenth Edition, 2016.
[0209] Imazamox may be applied to vegetation or areas adjacent to vegetation or to soil or water in an amount sufficient to induce a herbicidal effect to prevent the emergence or growth of vegetation. In some aspects, imazamox is applied to vegetation or an area adjacent to vegetation or to soil or water in an amount to prevent emergence or growth of vegetation: 5 g ai / ha or more, such as 6 g ai / ha or more, 7 g ai / ha or more, 8 g ai / ha or more, 9 g ai / ha or more, 10 g ai / ha or more, 11 g ai / ha or more, 12 g ai / ha or more, 13 g ai / ha or more, 14 g ai / ha or more, 15 g ai / ha or more, 16 g ai / ha or more, 17 g ai / ha or more, 18 g ai / ha or more, 19 g ai / ha or more, 20 g ai / ha or more, 21 g ai / ha or more, 22 g ai / ha or more, 23 g ai / ha or more, 24 g ai / ha or more, 25 g ai / ha or more, 26 g ai / ha or more, 27 g ai / ha or more, 28 g ai / ha or more g ai / ha or more, 29g ai / ha or more, 30g ai / ha or more, 32g ai / ha or more, 34g ai / ha or more, 36g ai / ha or more, 38g ai / ha or more, 40g ai / ha or more, 44g ai / ha or more, 46g ai / ha or more, 48g ai / ha or more, 50g ai / ha or more, 52g ai / ha or more, 54g ai / ha or more, 56g ai / ha or more, or 58g ai / ha or more;In the following amounts: 60g ai / ha or less, such as 58g ai / ha or less, 56g ai / ha or less, 54g ai / ha or less, 52g ai / ha or less, 50g ai / ha or less, 48g ai / ha or less, 46g ai / ha or less, 44g ai / ha or less, 42g ai / ha or less, 40g ai / ha or less, 38g ai / ha or less, 36g ai / ha or less, 34g ai / ha or less, 32g ai / ha or less, 30g ai / ha or less, 29g ai / ha or less, 28g ai / ha or less, 27g ai / ha or less, 26g ai / ha or less, 25g ai / ha or less, 24g ai / ha or less, 23g ai / ha or less, 22g ai / ha or less. or less, 21g ai / ha or less, 20g ai / ha or less, 19g ai / ha or less, 18g ai / ha or less, 17g ai / ha or less, 16g ai / ha or less, 15g ai / ha or less, 14g ai / ha or less, 13g ai / ha or less, 12g ai / ha or less, 11g ai / ha or less, 10g ai / ha or less, 9g ai / ha or less, 8g ai / ha or less, 7g ai / ha or less, or 6g ai / ha or less; or in an amount ranging from any of the foregoing minimum values to any of the foregoing maximum values, such as 5-60g ai / ha, 5-52g ai / ha, 6-46g ai / ha, 6-54g ai / ha, 7-38g ai / ha, 7-50g ai / ha, 8-48g ai / ha, ai / ha, 9-45g ai / ha, 10-40g ai / ha, 10-58g ai / ha, 11-36g ai / ha, 12-54g ai / ha, 13-60g ai / ha, or 15-48g ai / ha. ; Mefenacet
[0210] Compositions and methods of the present disclosure may include imazapic or an agriculturally acceptable salt or ester thereof. Imazapic, as shown below, is an imidazolinone that provides pre- and post-emergence control of a wide range of annual and perennial weeds in grasslands, pastures, and non-arable areas. Imazapic and methods for preparing imazapic are known in the art. Its herbicidal activity is described in The Pesticide Manual, Seventeenth Edition, 2016.
[0211] Imazapic may be applied to vegetation or areas adjacent to vegetation or to soil or water in an amount sufficient to induce a herbicidal effect to prevent the emergence or growth of vegetation. In some aspects, imazapic is applied to vegetation or an area adjacent to vegetation or to soil or water in an amount to prevent emergence or growth of vegetation: 17.5 g ai / ha or more, such as 18 g ai / ha or more, 19 g ai / ha or more, 20 g ai / ha or more, 22 g ai / ha or more, 24 g ai / ha or more, 26 g ai / ha or more, 28 g ai / ha or more, 30 g ai / ha or more, 35 g ai / ha or more, 40 g ai / ha or more, 45 g ai / ha or more, 50 g ai / ha or more, 45 g ai / ha or more, 50 g ai / ha or more, 60 g ai / ha or more, 70 g ai / ha or more, 80 g ai / ha or more, 90 g ai / ha or more, 100 g ai / ha or more, 110 g ai / ha or more, 120 g ai / ha or more, 130 g ai / ha or more. g ai / ha or more, 140 g ai / ha or more, 150 g ai / ha or more, 155 g ai / ha or more, 160 g ai / ha or more, 165 g ai / ha or more, 170 g ai / ha or more, 175 g ai / ha or more, 180 g ai / ha or more, 185 g ai / ha or more, 190 g ai / ha or more, 195 g ai / ha or more, 200 g ai / ha or more, 205 g ai / ha or more, 210 g ai / ha or more, or 215 g ai / ha or more;In the following amounts: 220 g ai / ha or less, such as 215 g ai / ha or less, 210 g ai / ha or less, 205 g ai / ha or less, 200 g ai / ha or less, 195 g ai / ha or less, 190 g ai / ha or less, 185 g ai / ha or less, 180 g ai / ha or less, 175 g ai / ha or less, 170 g ai / ha or less, 165 g ai / ha or less, 160 g ai / ha or less, 155 g ai / ha or less, 150 g ai / ha or less, 140 g ai / ha or less, 130 g ai / ha or less, 120 g ai / ha or less, 110 g ai / ha or less, 100 g ai / ha or less, 90 g ai / ha or less, 80 g ai / ha or less. g ai / ha or less, 70 g ai / ha or less, 60 g ai / ha or less, 50 g ai / ha or less, 45 g ai / ha or less, 40 g ai / ha or less, 35 g ai / ha or less, 30 g ai / ha or less, 28 g ai / ha or less, 26 g ai / ha or less, 24 g ai / ha or less, 22 g ai / ha or less, 20 g ai / ha or less, 19 g ai / ha or less, or 18 g ai / ha or less; or in an amount ranging from any of the foregoing minimum values to any of the foregoing maximum values, such as 17.5-220 g ai / ha, 17.5-210 g ai / ha, 18-200 g ai / ha, 19-120 g ai / ha, 20-210 g ai / ha, 20-170 g ai / ha, ai / ha, 22-190g ai / ha, 24-175g ai / ha, 26-210g ai / ha, 26-160g ai / ha, 30-190g ai / ha, 30-140gai / ha, 35-220g ai / ha, or 45-215g ai / ha. ; Methamphetamine
[0212] The compositions and methods of the present disclosure may include methotrexate or an agriculturally acceptable salt or ester thereof. Methotrexate, as shown below, is an imidazolinone that provides pre-emergence and post-emergence control of annual and perennial grass weeds, broadleaf weeds, shrubs, and trees. Methotrexate and methods for preparing methotrexate are known in the art. Its herbicidal activity is described in The Pesticide Manual, Seventeenth Edition, 2016.
[0213] Methapyr may be applied to vegetation or areas adjacent to vegetation or to soil or water in an amount sufficient to induce a herbicidal effect to prevent the emergence or growth of vegetation. In some aspects, imazapyr is applied to vegetation or an area adjacent to vegetation or to soil or water in an amount to prevent emergence or growth of vegetation: 100 g ai / ha or more, such as 120 g ai / ha or more, 125 g ai / ha or more, 130 g ai / ha or more, 140 g ai / ha or more, 150 g ai / ha or more, 160 g ai / ha or more, 170 g ai / ha or more, 180 g ai / ha or more, 190 g ai / ha or more, 200 g ai / ha or more, 225 g ai / ha or more, 250 g ai / ha or more, 275 g ai / ha or more, 300 g ai / ha or more, 325 g ai / ha or more, 350 g ai / ha or more, 375 g ai / ha or more, 400 g ai / ha or more, 425 g ai / ha or more, 450 g ai / ha or more, 1400g ai / ha or more, 1450g ai / ha or more, 1500g ai / ha or more, 1550g ai / ha or more, 1600g ai / ha or more, 1620g ai / ha or more, 1640g ai / ha or more, 1660g ai / ha or more, 1670g ai / ha or more, 1680g ai / ha or more, 1700g ai / ha or more, 1750g ai / ha or more, 1800g ai / ha or more, 1800g ai / ha or more, 1800g ai / ha or more, 1800g ai / ha or more, 1800g ai / ha or more, 1800g ai / ha or more, 1800g ai / ha or more, 1800g ai / ha or more, 1800g ai / ha or more, 1800g ai / ha or more ai / ha or more, or 1680g ai / ha or more;In the following amounts: 1700 g ai / ha or less (e.g., 1680 g ai / ha or less, 1660 g ai / ha or less, 1640 g ai / ha or less, 1620 g ai / ha or less, 1600 g ai / ha or less, 1550 g ai / ha or less, 1500 g ai / ha or less, 1450 g ai / ha or less, 1400 g ai / ha or less, 1350 g ai / ha or less, 1300 g ai / ha or less, 1250 g ai / ha or less, 1200 g ai / ha or less, 1150 g ai / ha or less, 1100 g ai / ha or less, 1050 g ai / ha or less, 1000 g ai / ha or less, 900 g ai / ha or less, 800 g ai / ha or less g ai / ha or less, 700 g ai / ha or less, 600 g ai / ha or less, 500 g ai / ha or less, 475 g ai / ha or less, 450 g ai / ha or less, 425 g ai / ha or less, 400 g ai / ha or less, 375 g ai / ha or less, 350 g ai / ha or less, 325 g ai / ha or less, 300 g ai / ha or less, 275 g ai / ha or less, 250 g ai / ha or less, 225 g ai / ha or less, 200 g ai / ha or less, 190 g ai / ha or less, 180 g ai / ha or less, 170 g ai / ha or less, 160 g ai / ha or less, 150 g ai / ha or less, 140 g ai / ha or less, 130 g ai / ha or less g ai / ha, 125-850 g ai / ha, 130-700 g ai / ha, 150-1000 g ai / ha, 160-475 g ai / ha, 170-1660 g ai / ha, 180-1500 g ai / ha, 190-1050 g ai / ha, 200-700 g ai / ha, 250-1500 g ai / ha, 325-1200 g ai / ha, 450-1500 g ai / ha, 500-900 g ai / ha, ai / ha, or 110-1000gai / ha. ; Imidazole
[0214] Compositions and methods of the present disclosure may include imidacloprid or an agriculturally acceptable salt or ester thereof. Imidazolinone, as shown below, is an imidazolinone that controls many of the major annual and perennial grass and broadleaf weeds in most major crops. Imidazolinone and methods for preparing imidacloprid are known in the art. Its herbicidal activity is described in The Pesticide Manual, Seventeenth Edition, 2016.
[0215] Imidazolin may be applied to vegetation or areas adjacent to vegetation or to soil or water in an amount sufficient to induce a herbicidal effect to prevent the emergence or growth of vegetation. In some aspects, imazethapyr is applied to vegetation or an area adjacent to vegetation or to soil or water in an amount to prevent emergence or growth of vegetation: 8.75 g ai / ha or more, such as 9 g ai / ha or more, 10 g ai / ha or more, 11 g ai / ha or more, 12 g ai / ha or more, 13 g ai / ha or more, 14 g ai / ha or more, 15 g ai / ha or more, 16 g ai / ha or more, 18 g ai / ha or more, 20 g ai / ha or more, 25 g ai / ha or more, 30 g ai / ha or more, 35 g ai / ha or more, 40 g ai / ha or more, 45 g ai / ha or more, 50 g ai / ha or more, 60 g ai / ha or more, 70 g ai / ha or more, 80 g ai / ha or more, 90 g ai / ha or more, 100 g ai / ha or more, 120 g ai / ha or more. g ai / ha or more, 130 g ai / ha or more, 140 g ai / ha or more, 150 g ai / ha or more, 160 g ai / ha or more, 170 g ai / ha or more, 180 g ai / ha or more, 190 g ai / ha or more, 200 g ai / ha or more, 210 g ai / ha or more, 220 g ai / ha or more, 230 g ai / ha or more, 240 g ai / ha or more, 250 g ai / ha or more, 260 g ai / ha or more, 270 g ai / ha or more, 272 g ai / ha or more, 274 g ai / ha or more, 276 g ai / ha or more, or 278 g ai / ha or more;In the following amounts: 280g ai / ha or less, such as 278g ai / ha or less, 276g ai / ha or less, 274g ai / ha or less, 272g ai / ha or less, 270g ai / ha or less, 260g ai / ha or less, 250g ai / ha or less, 240g ai / ha or less, 230g ai / ha or less, 220g ai / ha or less, 210g ai / ha or less, 200g ai / ha or less, 190g ai / ha or less, 180g ai / ha or less, 170g ai / ha or less, 160g ai / ha or less, 150g ai / ha or less, 140g ai / ha or less, 130g ai / ha or less, 120g ai / ha or less, 110g ai / ha or less g ai / ha or less, 100 g ai / ha or less, 90 g ai / ha or less, 80 g ai / ha or less, 70 g ai / ha or less, 60 g ai / ha or less, 50 g ai / ha or less, 45 g ai / ha or less, 40 g ai / ha or less, 35 g ai / ha or less, 30 g ai / ha or less, 25 g ai / ha or less, 20 g ai / ha or less, 18 g ai / ha or less, 16 g ai / ha or less, 15 g ai / ha or less, 14 g ai / ha or less, 13 g ai / ha or less, 12 g ai / ha or less, 11 g ai / ha or less, 10 g ai / ha or less, or 9 g ai / ha or less; or in an amount ranging from any of the foregoing minimum values to any of the foregoing maximum values, such as 8.75-280 g ai / ha, 8.75-170g ai / ha, 9-220g ai / ha, 10-260g ai / ha, 10-150g ai / ha, 11-220g ai / ha, 12-200g ai / ha, 13-274g ai / ha, 15-230g ai / ha, 16-160g ai / ha, 18-280g ai / ha, 20-210g ai / ha, 20-190g ai / ha, or 25-272g ai / ha. ; Pyrimidinyloxybenzoate herbicides
[0216] In some aspects, the composition contains a herbicidally effective amount of a compound according to Formula I, and (b) bispyribac-butyl, pyrimidinesulfuron, pyraclostrobin, pyrimidinesulfuron, pyrimidinesulfuron, or an agriculturally acceptable salt or ester thereof, or a combination thereof. Bispyribac-sodium
[0217] The compositions and methods of the present disclosure may include bispyribac-sodium or an agriculturally acceptable salt or ester thereof. Bispyribac-sodium, as shown below, is a pyrimidinyloxybenzoate that provides control of grass weeds, sedges, and broadleaf weeds in, for example, direct-seeded and water-seeded rice and turf. Bispyribac-sodium and methods for preparing bispyribac-sodium are known in the art. Its herbicidal activity is described in The Pesticide Manual, Seventeenth Edition, 2016.
[0218] Bispyribac-sodium may be applied to vegetation or areas adjacent to vegetation or to soil or water in an amount sufficient to induce a herbicidal action to prevent the emergence or growth of vegetation. In some aspects, bispyribac-sodium is applied to vegetation or to an area adjacent to vegetation or to soil or water in an amount of 5 g ai / ha or more, such as 7.5 g ai / ha or more, 10 g ai / ha or more, 12.5 g ai / ha or more, 15 g ai / ha or more, 17.5 g ai / ha or more, 20 g ai / ha or more, 22.5 g ai / ha or more, 25 g ai / ha or more, 27.5 g ai / ha or more, 30 g ai / ha or more, 32.5 g ai / ha or more, 35 g ai / ha or more, 37.5 g ai / ha or more, 40 g ai / ha or more, 42.5 g ai / ha or more, 45 g ai / ha or more, 47.5 g ai / ha or more, 50 g ai / ha or more, 52.5 g ai / ha or more, 55 g ai / ha or more, g ai / ha or more, 57.5 g ai / ha or more, 60 g ai / ha or more, 62.5 g ai / ha or more, 65 g ai / ha or more, 67.5 g ai / ha or more, 70 g ai / ha or more, 72.5 g ai / ha or more, 75 g ai / ha or more, 77.5 g ai / ha or more, 80 g ai / ha or more, 82.5 g ai / ha or more, 85 g ai / ha or more, 87.5 g ai / ha or more, 90 g ai / ha or more, 92.5 g ai / ha or more, 95 g ai / ha or more, 97.5 g ai / ha or more; in the following amounts: 100 g ai / ha or less, such as 97.5 g ai / ha or less, 95 g ai / ha or less, 92.5 g ai / ha or less, 90 g ai / ha or less, 87.5 g ai / ha or more ai / ha or less, 85g ai / ha or less, 82.5g ai / ha or less, 80g ai / ha or less, 77.5g ai / ha or less, 75g ai / ha or less, 72.5g ai / ha or less, 70g ai / ha or less, 67.5g ai / ha or less, 65g ai / ha or less, 62.5g ai / ha or less, 60g ai / ha or less, 57.5g ai / ha or less, 55g ai / ha or less, 52.5g ai / ha or less, 50g ai / ha or less, 47.5g ai / ha or less, 45g ai / ha or less, 42.5g ai / ha or less, 40g ai / ha or less, 37.or an amount ranging from any of the foregoing minimum values to any of the foregoing maximum values, such as 5-100 g ai / ha, 5-90 g ai / ha, 7.5-45 g ai / ha, 10-55 g ai / ha, 15-90 g ai / ha, 20-50 g ai / ha, 22.5-90 g ai / ha, 25-52.5 g ai / ha, ai / ha, 25-80gai / ha, 25-65g ai / ha, 27.5-60g ai / ha, 27.5-47.5g ai / ha, 30-85g ai / ha, or 40-95g ai / ha. . Fenpyrimidine oxime
[0219] Compositions and methods of the present disclosure may include sulfamethoxam or an agriculturally acceptable salt or ester thereof. Safeoxam, as shown below, is a pyrimidinyloxybenzoate that provides post-emergence control of barnyardgrass, blackgrass, and Polygonum species in rice, wheat, and Zoysia. Safeoxam and methods for preparing Safeoxam are known in the art. Its herbicidal activity is described, for example, in The Pesticide Manual, Seventeenth Edition, 2016.
[0220] Safenac may be applied to vegetation or areas adjacent to vegetation or to soil or water in an amount sufficient to induce a herbicidal action to prevent the emergence or growth of vegetation. In some aspects, saflufenacil is applied to vegetation or to an area adjacent to vegetation or to soil or water in an amount to prevent emergence or growth of vegetation: 7.5 g ai / ha or more, such as 8 g ai / ha or more, 9 g ai / ha or more, 10 g ai / ha or more, 11 g ai / ha or more, 12 g ai / ha or more, 13 g ai / ha or more, 14 g ai / ha or more, 15 g ai / ha or more, 16 g ai / ha or more, 17 g ai / ha or more, 18 g ai / ha or more, 19 g ai / ha or more, 20 g ai / ha or more, 22 g ai / ha or more, 24 g ai / ha or more, 26 g ai / ha or more, 28 g ai / ha or more, 30 g ai / ha or more, 32 g ai / ha or more, 34 g ai / ha or more, 36 g ai / ha or more, 38 g ai / ha or more. g ai / ha or more, 40g ai / ha or more, 42g ai / ha or more, 44g ai / ha or more, 46g ai / ha or more, 48g ai / ha or more, 50g ai / ha or more, 52g ai / ha or more, 54g ai / ha or more, 56g ai / ha or more, 58g ai / ha or more, 60g ai / ha or more, 62g ai / ha or more, 64g ai / ha or more, 66g ai / ha or more, 68g ai / ha or more, or 69g ai / ha or more;In amounts such as 70 g ai / ha or less, such as 69 g ai / ha or less, 68 g ai / ha or less, 66 g ai / ha or less, 64 g ai / ha or less, 62 g ai / ha or less, 60 g ai / ha or less, 58 g ai / ha or less, 56 g ai / ha or less, 54 g ai / ha or less, 52 g ai / ha or less, 50 g ai / ha or less, 48 g ai / ha or less, 46 g ai / ha or less, 44 g ai / ha or less, 42 g ai / ha or less, 40 g ai / ha or less, 38 g ai / ha or less, 36 g ai / ha or less, 34 g ai / ha or less, 32 g ai / ha or less, 30 g ai / ha or less, 28 g ai / ha or less, 26 g ai / ha or less. g ai / ha or less, 24g ai / ha or less, 22g ai / ha or less, 20g ai / ha or less, 19g ai / ha or less, 18g ai / ha or less, 17g ai / ha or less, 16g ai / ha or less, 15g ai / ha or less, 14g ai / ha or less, 13g ai / ha or less, 12g ai / ha or less, 11g ai / ha or less, 10g ai / ha or less, 9g ai / ha or less, or 8g ai / ha or less; or in an amount ranging from any of the above minimum values to any of the above maximum values, such as 7.5-70g ai / ha, 7.5-78g ai / ha, 7.5-72g ai / ha, 8-90g ai / ha, 9-120g ai / ha, 9-180g ai / ha, 10-190g ai / ha, 11-20g ai / ha, 12-25g ai / ha, 13-26g ai / ha, 14-27g ai / ha, 15-28g ai / ha ai / ha, 10-44g ai / ha, 10-40g ai / ha, 11-62g ai / ha, 12-46g ai / ha, 13-70g ai / ha, 15-54g ai / ha, or 20-64g ai / ha. ; Cyclamate
[0221] The compositions and methods of the present disclosure may include cypermethrin or its agriculturally acceptable salt or ester. Cypermethrin, as shown below, is a pyrimidinyloxybenzoate that provides control of grass weeds in rice. Cypermethrin and methods for preparing cypermethrin are known in the art. Its herbicidal activity is described in, for example, The Pesticide Manual, 17th edition, 2016.
[0222] Cypermethrin may be applied to vegetation or areas adjacent to vegetation or to soil or water in an amount sufficient to induce a herbicidal effect to prevent the emergence or growth of vegetation. In some aspects, cypermethrin is applied to vegetation or an area adjacent to vegetation or to soil or water in an amount to prevent emergence or growth of vegetation: 20 g ai / ha or more, such as 22 g ai / ha or more, 25 g ai / ha or more, 30 g ai / ha or more, 35 g ai / ha or more, 40 g ai / ha or more, 45 g ai / ha or more, 50 g ai / ha or more, 55 g ai / ha or more, 60 g ai / ha or more, 70 g ai / ha or more, 80 g ai / ha or more, 90 g ai / ha or more, 100 g ai / ha or more, 120 g ai / ha or more, 130 g ai / ha or more, 140 g ai / ha or more, 150 g ai / ha or more, 160 g ai / ha or more, 170 g ai / ha or more, 180 g ai / ha or more, 190 g ai / ha or more. g ai / ha or more, 200 g ai / ha or more, 210 g ai / ha or more, 220 g ai / ha or more, 230 g ai / ha or more, 240 g ai / ha or more, 250 g ai / ha or more, 260 g ai / ha or more, 270 g ai / ha or more, 280 g ai / ha or more, 290 g ai / ha or more, 300 g ai / ha or more, 310 g ai / ha or more, 320 g ai / ha or more, 330 g ai / ha or more, 340 g ai / ha or more, or 345 g ai / ha or more;In the following amounts: 350g ai / ha or less, such as 345g ai / ha or less, 340g ai / ha or less, 330g ai / ha or less, 320g ai / ha or less, 310g ai / ha or less, 300g ai / ha or less, 290g ai / ha or less, 280g ai / ha or less, 270g ai / ha or less, 260g ai / ha or less, 250g ai / ha or less, 240g ai / ha or less, 230g ai / ha or less, 220g ai / ha or less, 210g ai / ha or less, 200g ai / ha or less, 190g ai / ha or less, 180g ai / ha or less, 170g ai / ha or less, 160g ai / ha or less, 150g ai / ha or less or less, 140 g ai / ha or less, 130 g ai / ha or less, 120 g ai / ha or less, 110 g ai / ha or less, 100 g ai / ha or less, 90 g ai / ha or less, 80 g ai / ha or less, 70 g ai / ha or less, 60 g ai / ha or less, 55 g ai / ha or less, 50 g ai / ha or less, 45 g ai / ha or less, 40 g ai / ha or less, 35 g ai / ha or less, 30 g ai / ha or less, 25 g ai / ha or less, or 22 g ai / ha or less; or in an amount ranging from any of the foregoing minimum values to any of the foregoing maximum values, such as 20-350 g ai / ha, 55-170 g ai / ha, 22-220 g ai / ha, 70-260 g ai / ha ai / ha, 30-250g ai / ha, 45-220g ai / ha, 80-200g ai / ha, 130-270g ai / ha, 150-330gai / ha, 60-160g ai / ha, 180-345g ai / ha, 210-310g ai / ha, 90-190g ai / ha, or 22-340g ai / ha. ; Pyrimidine
[0223] The compositions and methods of the present disclosure may include pyrimidine butyl or an agriculturally acceptable salt or ester thereof. Pyrimidine butyl, as shown below, is a pyrimidinyloxybenzoate that provides post-emergence control of Echinochloa species in rice. Pyrimidine butyl and methods for preparing pyrimidine butyl are known in the art. Its herbicidal activity is described, for example, in The Pesticide Manual, Seventeenth Edition, 2016.
[0224] Pyrimidine may be applied to vegetation or areas adjacent to vegetation or to soil or water in an amount sufficient to induce a herbicidal effect to prevent the emergence or growth of vegetation. In some aspects, apyrimidine is applied to vegetation or an area adjacent to vegetation or to soil or water in an amount of 20 g ai / ha or more, such as 22 g ai / ha or more, 25 g ai / ha or more, 30 g ai / ha or more, 35 g ai / ha or more, 40 g ai / ha or more, 45 g ai / ha or more, 50 g ai / ha or more, 60 g ai / ha or more, 70 g ai / ha or more, 80 g ai / ha or more, 90 g ai / ha or more, 100 g ai / ha or more, 120 g ai / ha or more, 130 g ai / ha or more, 140 g ai / ha or more, 150 g ai / ha or more, 160 g ai / ha or more, or 170 g ai / ha or more; in an amount of 175 g ai / ha or less, such as 170 g ai / ha or less, 160 g ai / ha or more g ai / ha or less, 150 g ai / ha or less, 140 g ai / ha or less, 130 g ai / ha or less, 120 g ai / ha or less, 110 g ai / ha or less, 100 g ai / ha or less, 90 g ai / ha or less, 80 g ai / ha or less, 70 g ai / ha or less, 60 g ai / ha or less, 50 g ai / ha or less, 45 g ai / ha or less, 40 g ai / ha or less, 35 g ai / ha or less, 30 g ai / ha or less, 25 g ai / ha or less, or 22 g ai / ha or less; or in an amount ranging from any of the foregoing minimum values to any of the foregoing maximum values, such as 20-175 g ai / ha, 22-170 g ai / ha, 35-120 g ai / ha, 100-160 g ai / ha ai / ha, 40-150g ai / ha, 80-120g ai / ha, 25-110g ai / ha, 90-150g ai / ha, 45-130g ai / ha, 60-160g ai / ha, 30-120gai / ha, 20-160g ai / ha, or 22-100g ai / ha. Sulfonylaminocarbonyltriazolinone herbicide
[0225] In some aspects, the composition contains a herbicidally effective amount of a compound according to Formula I, and (b) flucarbazone-methyl, propoxycarbazone-methyl, thiathrin-methyl, or an agriculturally acceptable salt or ester thereof, or a combination thereof. Flucarbazone
[0226] Compositions and methods of the present disclosure may include flucarbazine or an agriculturally acceptable salt or ester thereof. Flucarbazine, as shown below, is a sulfonylamino-carbonyl triazolinone that provides post-emergence control of annual grass weeds and some perennial grass weeds and some broadleaf weeds. Flucarbazine and methods for preparing flucarbazine are known in the art. Its herbicidal activity is described in The Pesticide Manual, Seventeenth Edition, 2016.
[0227] Flucarbazone may be applied to vegetation or areas adjacent to vegetation or to soil or water in an amount sufficient to induce a herbicidal action to prevent the emergence or growth of vegetation. In some aspects, flucarbazine is applied to vegetation or to an area adjacent to vegetation or to soil or water in an amount to prevent emergence or growth of vegetation: 3.75 g ai / ha or more, such as 4 g ai / ha or more, 4.25 g ai / ha or more, 4.5 g ai / ha or more, 4.75 g ai / ha or more, 5 g ai / ha or more, 5.25 g ai / ha or more, 5.5 g ai / ha or more, 5.75 g ai / ha or more, 6 g ai / ha or more, 7 g ai / ha or more, 7.5 g ai / ha or more, 8 g ai / ha or more, 9 g ai / ha or more, 10 g ai / ha or more, 11 g ai / ha or more, 12 g ai / ha or more, 13 g ai / ha or more, 14 g ai / ha or more, 15 g ai / ha or more, 16 g ai / ha or more, 17 g ai / ha or more, 18 g ai / ha or more. g ai / ha or more, 19 g ai / ha or more, 20 g ai / ha or more, 21 g ai / ha or more, 22 g ai / ha or more, 23 g ai / ha or more, 24 g ai / ha or more, 25 g ai / ha or more, 25.5 g ai / ha or more, 26 g ai / ha or more, 26.5 g ai / ha or more, 27 g ai / ha or more, 27.5 g ai / ha or more, 28 g ai / ha or more, 28.5 g ai / ha or more, 29 g ai / ha or more, 29.25 g ai / ha or more, 29.5 g ai / ha or more, or 29.75 g ai / ha or more; in amounts of 30 g ai / ha or less, such as 29.75 g ai / ha or less, 29.5 g ai / ha or less, 29.25 g ai / ha or less, 29 g ai / ha or more, ai / ha or less, 28.5g ai / ha or less, 28g ai / ha or less, 27.5g ai / ha or less, 27g ai / ha or less, 26.5g ai / ha or less, 26g ai / ha or less, 25g ai / ha or less, 24g ai / ha or less, 23g ai / ha or less, 22g ai / ha or less, 21g ai / ha or less, 20g ai / ha or less, 19g ai / ha or less, 18g ai / ha or less, 17g ai / ha or less, 16g ai / ha or less, 15g ai / ha or less, 14g ai / ha or less, 13g ai / ha or less, 12g ai / ha or less, 11g ai / ha or less, 10g ai / ha or less, 9g ai / ha or less, 8g ai / ha or less, 7.5g ai / ha or less, 7g ai / ha or less, 6g ai / ha or less, 5.75g ai / ha or less, 5.5g ai / ha or less g ai / ha, 7-25g ai / ha, 7.5-30g ai / ha, 7.5-21g ai / ha, 8-25g ai / ha, 9-19g ai / ha, or 10-28.5g ai / ha. ai / ha. . Propylsulfuron
[0228] Compositions and methods of the present disclosure may include propoxysulfuron or an agriculturally acceptable salt or ester thereof. Propoxysulfuron, as shown below, is a sulfonylaminocarbonyl triazolinone that provides post-emergence control of grass weeds and some broadleaf weeds. Propoxysulfuron and methods for preparing propoxysulfuron are known in the art. Its herbicidal activity is described in The Pesticide Manual, Seventeenth Edition, 2016.
[0229] Probensulfuron-methyl may be applied to vegetation or areas adjacent to vegetation or to soil or water in an amount sufficient to induce a herbicidal effect to prevent the emergence or growth of vegetation. In some aspects, propensulfuron-methyl is applied to vegetation or an area adjacent to vegetation or to soil or water in an amount to prevent emergence or growth of vegetation: 3.75 g ai / ha or more, such as 4 g ai / ha or more, 4.25 g ai / ha or more, 4.5 g ai / ha or more, 4.75 g ai / ha or more, 5 g ai / ha or more, 6 g ai / ha or more, 7 g ai / ha or more, 8 g ai / ha or more, 9 g ai / ha or more, 10 g ai / ha or more, 12 g ai / ha or more, 14 g ai / ha or more, 16 g ai / ha or more, 18 g ai / ha or more, 20 g ai / ha or more, 22 g ai / ha or more, 24 g ai / ha or more, 26 g ai / ha or more, 28 g ai / ha or more, 30 g ai / ha or more, 32 g ai / ha or more, 34 g ai / ha or more. g ai / ha or more, 36g ai / ha or more, 38g ai / ha or more, 40g ai / ha or more, 42g ai / ha or more, 44g ai / ha or more, 46g ai / ha or more, 48g ai / ha or more, 50g ai / ha or more, 52g ai / ha or more, 54g ai / ha or more, 56g ai / ha or more, 58g ai / ha or more, 60g ai / ha or more, 61g ai / ha or more, 62g ai / ha or more, 63g ai / ha or more, 64g ai / ha or more, 65g ai / ha or more, 66g ai / ha or more, 67g ai / ha or more, 68g ai / ha or more, or 69g ai / ha or more;In the following amounts: 70g ai / ha or less, such as 69g ai / ha or less, 68g ai / ha or less, 67g ai / ha or less, 66g ai / ha or less, 65g ai / ha or less, 64g ai / ha or less, 63g ai / ha or less, 62g ai / ha or less, 61g ai / ha or less, 60g ai / ha or less, 58g ai / ha or less, 56g ai / ha or less, 54g ai / ha or less, 52g ai / ha or less, 50g ai / ha or less, 48g ai / ha or less, 46g ai / ha or less, 44g ai / ha or less, 42g ai / ha or less, 40g ai / ha or less, 38g ai / ha or less, 36g ai / ha or less, 34g ai / ha or less. or less, 32g ai / ha or less, 30g ai / ha or less, 28g ai / ha or less, 26g ai / ha or less, 24g ai / ha or less, 22g ai / ha or less, 20g ai / ha or less, 28g ai / ha or less, 16g ai / ha or less, 14g ai / ha or less, 12g ai / ha or less, 10g ai / ha or less, 9g ai / ha or less, 8g ai / ha or less, 7g ai / ha or less, 6g ai / ha or less, 5g ai / ha or less, 4.75g ai / ha or less, 4.5g ai / ha or less, 4.25g ai / ha or less, or 4g ai / ha or less; or in an amount ranging from any of the foregoing minimum values to any of the foregoing maximum values, such as 3.75-70g ai / ha ai / ha, 4-68g ai / ha, 4.25-56g ai / ha, 4.5-28g ai / ha, 5-62g ai / ha, 5-38g ai / ha, 7-70g ai / ha, 8-52g ai / ha, 9-40gai / ha, 10-70g ai / ha, 10-24g ai / ha, 12-69g ai / ha, 14-65gai / ha, or 20-58g ai / ha. ; Thiazolamide
[0230] Compositions and methods of the present disclosure may include thiazolinone or its agriculturally acceptable salt or ester. Thiazolinone-methyl, as shown below, is a sulfonylaminocarbonyl triazolinone that provides post-emergence control of grass weeds and some broadleaf weeds. Thiazolinone and methods for preparing thiazolinone are known in the art. Its herbicidal activity is described in The Pesticide Manual, 17th edition, 2016.
[0231] Thiazonsulfuron-methyl can be applied to vegetation or areas adjacent to vegetation or to soil or water in an amount sufficient to induce herbicidal action to prevent the emergence or growth of vegetation. In some aspects, thiazonsulfuron-methyl is applied to vegetation or areas adjacent to vegetation or to soil or water in an amount of 2.5 g ai / ha or more, such as 2.75 g ai / ha or more, 3 g ai / ha or more, 3.25 g ai / ha or more, 3.5 g ai / ha or more, 3.75 g ai / ha or more, 4 g ai / ha or more, 4.25 g ai / ha or more, 4.5 g ai / ha or more, 4.75g ai / ha or more, 5g ai / ha or more, 6g ai / ha or more, 7g ai / ha or more, 8g ai / ha or more, 9g ai / ha or more, 10g ai / ha or more, 12g ai / ha or more, 14g ai / ha or more, 16g ai / ha or more, 18g ai / ha or more, 20g ai / ha or more, 22g ai / ha or more, 24g ai / ha or more, 26g ai / ha or more, 28g ai / ha or more, 30g ai / ha or more, 31g ai / ha or more, 32g ai / ha or more, 33g ai / ha or more, 34g ai / ha or more, 35g ai / ha or more, 36g ai / ha or more, 37g ai / ha or more, 38g ai / ha or more, 39g ai / ha or more, 40g ai / ha or more, 41g ai / ha or more in the following amounts: 45g ai / ha or less, such as 44g ai / ha or less, 43g ai / ha or less, 42g ai / ha or less, 41g ai / ha or less, 40g ai / ha or less, 39g ai / ha or less, 38g ai / ha or less, 37g ai / ha or less, 36g ai / ha or less, 35g ai / ha or less, 34g ai / ha or less, 33g ai / ha or less, 32g ai / ha or less, 31g ai / ha or less, 30g ai / ha or less, 28g ai / ha or less, 26g ai / ha or less, 24g ai / ha or less, 22g ai / ha or less, 20g or less, 18 g ai / ha or less, 16 g ai / ha or less, 14 g ai / ha or less, 12 g ai / ha or less, 10 g ai / ha or less, 9 g ai / ha or less, 8 g ai / ha or less, 7 g ai / ha or less, 6 g ai / ha or less, 5 g ai / ha or less, 4.75 g ai / ha or less, 4.5 g ai / ha or less, 4.25 g ai / ha or less, 4 g ai / ha or less, 3.75 g ai / ha or less, 3.5 g ai / ha or less, 3.25 g ai / ha or less, 3 g ai / ha or less, or 2.75 g ai / ha or less, or in an amount ranging from any of the foregoing minimum values to any of the foregoing maximum values, such as 2.5-45 g ai / ha, 2.5-41 g ai / ha, ai / ha, 2.75-39gai / ha, 2.75-37gai / ha, 3-40g ai / ha, 3-33g ai / ha, 3.25-28g ai / ha, 3.5-45g ai / ha, 3.75-45g ai / ha, 4-39g ai / ha, 4.5-31g ai / ha, 5-45g ai / ha, 5-37g ai / ha, or 8-36g ai / ha. . Sulfonylurea herbicides
[0232] In some aspects, the composition contains a herbicidally effective amount of a compound according to Formula I, and (b) acylosulfuron-methyl, tetrazosulfuron-methyl, benzylsulfuron-methyl, chlorimuron-methyl, chlorsulfuron-methyl, ethoxysulfuron-methyl, flazasulfuron-methyl, fluazifop-methyl, fluazifop-methyl, foramsulfuron-methyl, chlorpyrasulfuron-methyl, azole pyrasulfuron-methyl, iodosulfuron-methyl, iodofensulfuron-methyl, mesosulfuron-methyl, chlorpyrasulfuron-methyl, metsulfuron-methyl, nicosulfuron-methyl, pyrimidinesulfuron-methyl, epoxysulfuron-methyl, primisulfuron-methyl, promazinesulfuron-methyl, trifloxysulfuron-methyl, pyrazosulfuron-methyl, sulfonesulfuron-methyl, sulfosulfuron-methyl, etherbensulfuron-methyl, bensulfuron-methyl, thifensulfuron-methyl, trifloxysulfuron-methyl, trifloxysulfuron-methyl, or an agriculturally acceptable salt or ester thereof, or a combination thereof. Amidosulfuron
[0233] Compositions and methods of the present disclosure may include amidosulfuron or an agriculturally acceptable salt or ester thereof. Amidosulfuron, as shown below, is a sulfonylurea that provides post-emergence control of a wide range of broadleaf weeds such as cleavers in winter wheat, durum wheat, barley, rye, triticale, and oats. Amidosulfuron and methods for preparing amidosulfuron are known in the art. Its herbicidal activity is described in The Pesticide Manual, Seventeenth Edition, 2016.
[0234] Amidosulfuron may be applied to vegetation or areas adjacent to vegetation or to soil or water in an amount sufficient to induce a herbicidal action to prevent the emergence or growth of vegetation. In some aspects, amidosulfuron-methyl is applied to vegetation or to an area adjacent to vegetation or to soil or water in an amount to prevent emergence or growth of vegetation: 3.75 g ai / ha or more, such as 4 g ai / ha or more, 4.25 g ai / ha or more, 4.5 g ai / ha or more, 4.75 g ai / ha or more, 5 g ai / ha or more, 6 g ai / ha or more, 7 g ai / ha or more, 8 g ai / ha or more, 9 g ai / ha or more, 10 g ai / ha or more, 11 g ai / ha or more, 12 g ai / ha or more, 13 g ai / ha or more, 14 g ai / ha or more, 15 g ai / ha or more, 16 g ai / ha or more, 17 g ai / ha or more, 18 g ai / ha or more, 19 g ai / ha or more, 20 g ai / ha or more, 22 g ai / ha or more, 24 g ai / ha or more. g ai / ha or more, 26g ai / ha or more, 28g ai / ha or more, 30g ai / ha or more, 32g ai / ha or more, 34g ai / ha or more, 36g ai / ha or more, 38g ai / ha or more, 40g ai / ha or more, 42g ai / ha or more, 44g ai / ha or more, 46g ai / ha or more, 48g ai / ha or more, 50g ai / ha or more, 51g ai / ha or more, 52g ai / ha or more, 53g ai / ha or more, 54g ai / ha or more, 55g ai / ha or more, 56g ai / ha or more, 57g ai / ha or more, 58g ai / ha or more, or 59g ai / ha or more;In the following amounts: 60g ai / ha or less, such as 59g ai / ha or less, 58g ai / ha or less, 57g ai / ha or less, 56g ai / ha or less, 55g ai / ha or less, 54g ai / ha or less, 53g ai / ha or less, 52g ai / ha or less, 51g ai / ha or less, 50g ai / ha or less, 48g ai / ha or less, 46g ai / ha or less, 44g ai / ha or less, 42g ai / ha or less, 40g ai / ha or less, 38g ai / ha or less, 36g ai / ha or less, 34g ai / ha or less, 32g ai / ha or less, 30g ai / ha or less, 28g ai / ha or less, 26g ai / ha or less, 24g ai / ha or less. g ai / ha or less, 22 g ai / ha or less, 20 g ai / ha or less, 19 g ai / ha or less, 18 g ai / ha or less, 17 g ai / ha or less, 16 g ai / ha or less, 15 g ai / ha or less, 14 g ai / ha or less, 13 g ai / ha or less, 12 g ai / ha or less, 11 g ai / ha or less, 10 g ai / ha or less, 9 g ai / ha or less, 8 g ai / ha or less, 7 g ai / ha or less, 6 g ai / ha or less, 5 g ai / ha or less, 4.75 g ai / ha or less, 4.5 g ai / ha or less, or 4.25 g ai / ha or less, or 4 g ai / ha or less; or in an amount ranging from any of the foregoing minimum values to any of the foregoing maximum values, such as 3.75-60 g ai / ha, 4-58g ai / ha, 4.5-51g ai / ha, 5-57g ai / ha, 5-30g ai / ha, 6-42g ai / ha, 8-50g ai / ha, 9-32g ai / ha, 10-53gai / ha, 12-30g ai / ha, or 13-40g ai / ha. ; Tetrazosulfuron
[0235] The compositions and methods of the present disclosure may include tetrazosulfuron or an agriculturally acceptable salt or ester thereof. Tetrazosulfuron, as shown below, is a sulfonylurea that provides post-emergence control of annual and perennial broadleaf weeds and sedge weeds, such as in rice. Tetrazosulfuron and methods for preparing tetrazosulfuron are known in the art. Its herbicidal activity is described in The Pesticide Manual, Seventeenth Edition, 2016.
[0236] Amidosulphonyl may be applied to vegetation or areas adjacent to vegetation or to soil or water in an amount sufficient to induce a herbicidal action to prevent the emergence or growth of vegetation. In some aspects, tetrazosulfuron-methyl is applied to vegetation or an area adjacent to vegetation or to soil or water in an amount to prevent emergence or growth of vegetation: 3.125 g ai / ha or more, such as 3.25 g ai / ha or more, 3.5 g ai / ha or more, 3.75 g ai / ha or more, 4 g ai / ha or more, 4.25 g ai / ha or more, 4.5 g ai / ha or more, 4.75 g ai / ha or more, 5 g ai / ha or more, 5.5 g ai / ha or more, 6 g ai / ha or more, 6.5 g ai / ha or more, 7 g ai / ha or more, 7.5 g ai / ha or more, 8 g ai / ha or more, 8.5 g ai / ha or more, 9 g ai / ha or more, 9.5 g ai / ha or more, 10 g ai / ha or more, 11 g ai / ha or more, 12 g ai / ha or more, 13 g ai / ha or more. g ai / ha or more, 14 g ai / ha or more, 15 g ai / ha or more, 16 g ai / ha or more, 17 g ai / ha or more, 18 g ai / ha or more, 19 g ai / ha or more, 20 g ai / ha or more, 20.5 g ai / ha or more, 21 g ai / ha or more, 21.5 g ai / ha or more, 22 g ai / ha or more, 22.5 g ai / ha or more, 22.75 g ai / ha or more, 23 g ai / ha or more, 23.25 g ai / ha or more, 23.5 g ai / ha or more, 23.75 g ai / ha or more, 24 g ai / ha or more, 24.25 g ai / ha or more, 24.5 g ai / ha or more, or 24.75 g ai / ha or more; in amounts as follows: 25 g ai / ha or less, such as 24.75 g ai / ha ai / ha or less, 24.5g ai / ha or less, 24.25g ai / ha or less, 24g ai / ha or less, 23.75g ai / ha or less, 23.5g ai / ha or less, 23.25g ai / ha or less, 23g ai / ha or less, 22.75g ai / ha or less, 22.5g ai / ha or less, 22g ai / ha or less, 21.5g ai / ha or less, 21g ai / ha or less, 20.5g ai / ha or less, 20g ai / ha or less, 19g ai / ha or less, 18g ai / ha or less, 17g ai / ha or less, 16g ai / ha or less, 15g ai / ha or less, 14g ai / ha or less, 13g ai / ha or less, 12g ai / ha or less, 11g ai / ha or less, 10g ai / ha or less, 9.5g ai / ha or less, 9g ai / ha or less, 8.5g ai / ha or less, 8g ai / ha or less, 7.5g ai / ha or less, 7g ai / ha or less, 6.5g ai / ha or less, 6g ai / ha or less, 5.5g ai / ha or less, 5g ai / ha or less, 4.75g ai / ha or less, 4.5g ai / ha or less g ai / ha, 4-25 g ai / ha, 4-23.25 g ai / ha, 4.25-20 g ai / ha, 4.5-18 g ai / ha, 4.75-22.75 g ai / ha, or 5-24 g ai / ha. ai / ha. . Bensulfuron-methyl
[0237] The compositions and methods of the present disclosure may include bensulfuron-methyl or an agriculturally acceptable salt or ester thereof. Bensulfuron-methyl, as shown below, is a sulfonylurea that provides pre- and post-emergence control of annual and perennial broadleaf weeds and sedges, such as in rice. Bensulfuron-methyl and methods for preparing bensulfuron-methyl are known in the art. Its herbicidal activity is described in The Pesticide Manual, Seventeenth Edition, 2016.
[0238] Bensulfuron-methyl may be applied to vegetation or areas adjacent to vegetation or to soil or water in an amount sufficient to induce a herbicidal action to prevent the emergence or growth of vegetation. In some aspects, benzylsulfuron-methyl is applied to vegetation or an area adjacent to vegetation or to soil or water in an amount to prevent emergence or growth of vegetation: 8.75 g ai / ha or more, such as 9 g ai / ha or more, 10 g ai / ha or more, 11 g ai / ha or more, 12 g ai / ha or more, 13 g ai / ha or more, 14 g ai / ha or more, 15 g ai / ha or more, 16 g ai / ha or more, 17 g ai / ha or more, 18 g ai / ha or more, 19 g ai / ha or more, 20 g ai / ha or more, 22 g ai / ha or more, 24 g ai / ha or more, 26 g ai / ha or more, 28 g ai / ha or more, 30 g ai / ha or more, 32 g ai / ha or more, 34 g ai / ha or more, 36 g ai / ha or more, 38 g ai / ha or more, 40 g ai / ha or more g ai / ha or more, 42g ai / ha or more, 44g ai / ha or more, 46g ai / ha or more, 48g ai / ha or more, 50g ai / ha or more, 52g ai / ha or more, 54g ai / ha or more, 56g ai / ha or more, 58g ai / ha or more, 60g ai / ha or more, 62g ai / ha or more, 64g ai / ha or more, 66g ai / ha or more, 68g ai / ha or more, or 69g ai / ha or more;In amounts such as 70 g ai / ha or less, such as 69 g ai / ha or less, 68 g ai / ha or less, 66 g ai / ha or less, 64 g ai / ha or less, 62 g ai / ha or less, 60 g ai / ha or less, 58 g ai / ha or less, 56 g ai / ha or less, 54 g ai / ha or less, 52 g ai / ha or less, 50 g ai / ha or less, 48 g ai / ha or less, 46 g ai / ha or less, 44 g ai / ha or less, 42 g ai / ha or less, 40 g ai / ha or less, 38 g ai / ha or less, 36 g ai / ha or less, 34 g ai / ha or less, 32 g ai / ha or less, 30 g ai / ha or less, 28 g ai / ha or less, 26 g ai / ha or less. g ai / ha or less, 24g ai / ha or less, 22g ai / ha or less, 20g ai / ha or less, 19g ai / ha or less, 18g ai / ha or less, 17g ai / ha or less, 16g ai / ha or less, 15g ai / ha or less, 14g ai / ha or less, 13g ai / ha or less, 12g ai / ha or less, 11g ai / ha or less, 10g ai / ha or less, or 9g ai / ha or less; or in an amount ranging from any of the foregoing minimum values to any of the foregoing maximum values, such as 8.75-70g ai / ha, 9-60g ai / ha, 10-65g ai / ha, 10-40g ai / ha, 10-28g ai / ha, 11-68g ai / ha, 11-54g ai / ha, ai / ha, 12-60g ai / ha, 12-42g ai / ha, 13-69g ai / ha, 14-56g ai / ha, 15-40g ai / ha, 20-46g ai / ha, or 20-69g ai / ha. ; Chlorsulfuron
[0239] The compositions and methods of the present disclosure may include chlorsulfuron or an agriculturally acceptable salt or ester thereof. Chlorsulfuron, as shown below, is a sulfonylurea that provides control of broadleaf weeds and annual grass weeds in, for example, wheat, barley, oats, rye, triticale, flax, and on non-crop land. Chlorsulfuron and methods for preparing chlorsulfuron are known in the art. Its herbicidal activity is described in The Pesticide Manual, Seventeenth Edition, 2016.
[0240] Chlorsulfuron may be applied to vegetation or areas adjacent to vegetation or to soil or water in an amount sufficient to induce a herbicidal action to prevent the emergence or growth of vegetation. In some aspects, chlorsulfuron is applied to vegetation or to areas adjacent to vegetation or to soil or water in an amount of 1.1 g ai / ha or more, such as 1.25 g ai / ha or more, 1.5 g ai / ha or more, 1.75 g ai / ha or more, 2 g ai / ha or more, 2.25 g ai / ha or more, 2.5 g ai / ha or more, 2.75 g ai / ha or more, 3 g ai / ha or more, 3.25 g ai / ha or more, 3.5 g ai / ha or more, 3.75 g ai / ha or more, 4 g ai / ha or more, 4.25 g ai / ha or more, 4.5 g ai / ha or more, 4.75 g ai / ha or more, 5 g ai / ha or more, 6 g ai / ha or more, 7 g ai / ha or more, 8 g ai / ha or more, 9 g ai / ha or more, 10 g ai / ha or more. , 11g ai / ha or more, 12g ai / ha or more, 13g ai / ha or more, 14g ai / ha or more, 15g ai / ha or more, 16g ai / ha or more, 17g ai / ha or more, 18g ai / ha or more, 19g ai / ha or more, 20g ai / ha or more, 22g ai / ha or more, 24g ai / ha or more, 26g ai / ha or more, 28g ai / ha or more, 30g ai / ha or more, 32g ai / ha or more, 34g ai / ha or more, 36g ai / ha or more, 38g ai / ha or more, 40g ai / ha or more, 42g ai / ha or more, 44g ai / ha or more, 46g ai / ha or more, 47g ai / ha or more, 48g ai / ha or more, 49g ai / ha or more, 50g ai / ha or more, 51g ai / ha or more, 52g ai / ha or more, 54g ai / ha or more, 56g ai / ha or more, 57g ai / ha or more, 58g ai / ha or more, 59g ai / ha or more, 60g ai / ha or more ai / ha or more, 51 g ai / ha or more, or 51.5 g ai / ha or more; in the following amounts: 52 g ai / ha or less, such as 51.5g ai / ha or less, 51g ai / ha or less, 50g ai / ha or less, 49g ai / ha or less, 48g ai / ha or less, 47g ai / ha or less, 46g ai / ha or less, 44g ai / ha or less, 42g ai / ha or less, 40g ai / ha or less, 38g ai / ha or less, 36g ai / ha or less, 34g ai / ha or less, 32g ai / ha or less, 30g ai / ha or less, 28g ai / ha or less, 26g ai / ha or less, 24g ai / ha or less, 22g ai / ha or less, 20g ai / ha or less, 19g ai / ha or less, 18g ai / ha or less, 17g ai / ha or less, 16g ai / ha or less, 15g ai / ha or less g ai / ha or less, 14g ai / ha or less, 13g ai / ha or less, 12g ai / ha or less, 11g ai / ha or less, 10g ai / ha or less, 9g ai / ha or less, 8g ai / ha or less, 7g ai / ha or less, 6g ai / ha or less, 5g ai / ha or less, 4.75g ai / ha or less, 4.5g ai / ha or less, or 4.25g ai / ha or less, 4g ai / ha or less, 3.75g ai / ha or less, 3.5g ai / ha or less, 3.25g ai / ha or less, 3g ai / ha or less, 2.75g ai / ha or less, 2.5g ai / ha or less, 2.25g ai / ha or less, 2g ai / ha or less, 1.75g ai / ha or less, 1 ai / ha or less, 1.5g ai / ha or less, or 1.25g ai / ha or less; or in an amount ranging from any of the above minimum values to any of the above maximum values, such as 1.1-52g ai / ha, 1.25-51.5g ai / ha, 1.5-30g ai / ha, 1.75-47g ai / ha, 2-26g ai / ha, 3-50g ai / ha, 4-38g ai / ha, 4.5-42g ai / ha, 5-51g ai / ha, 7-49g ai / ha, 9-32g ai / ha, 10-45g ai / ha, 12-52g ai / ha, or 15-48g ai / ha. Ethoxysulfuron
[0241] The compositions and methods of the present disclosure may include ethoxysulfuron or an agriculturally acceptable salt or ester thereof. Ethoxysulfuron, as shown below, is a sulfonylurea that provides control of broadleaf weeds and sedge weeds in, for example, cereals, rice, and sugarcane. Ethoxysulfuron and methods for preparing ethoxysulfuron are known in the art. Its herbicidal activity is described in The Pesticide Manual, Seventeenth Edition, 2016.
[0242] Ethoxysulfuron may be applied to vegetation or areas adjacent to vegetation or to soil or water in an amount sufficient to induce a herbicidal action to prevent the emergence or growth of vegetation. In some aspects, ethoxysulfuron-methyl is applied to vegetation or to an area adjacent to vegetation or to soil or water in an amount to prevent emergence or growth of vegetation: 5 g ai / ha or more, such as 6 g ai / ha or more, 7 g ai / ha or more, 8 g ai / ha or more, 9 g ai / ha or more, 10 g ai / ha or more, 11 g ai / ha or more, 12 g ai / ha or more, 13 g ai / ha or more, 14 g ai / ha or more, 15 g ai / ha or more, 16 g ai / ha or more, 17 g ai / ha or more, 18 g ai / ha or more, 19 g ai / ha or more, 20 g ai / ha or more, 22 g ai / ha or more, 24 g ai / ha or more, 26 g ai / ha or more, 28 g ai / ha or more, 30 g ai / ha or more, 32 g ai / ha or more, 34 g ai / ha or more, 36 g ai / ha or more g ai / ha or more, 38g ai / ha or more, 40g ai / ha or more, 45g ai / ha or more, 50g ai / ha or more, 55g ai / ha or more, 60g ai / ha or more, 65g ai / ha or more, 70g ai / ha or more, 75g ai / ha or more, 80g ai / ha or more, 85g ai / ha or more, 90g ai / ha or more, 95g ai / ha or more, 100g ai / ha or more, 101g ai / ha or more, 102g ai / ha or more, 103g ai / ha or more, 104g ai / ha or more, 105g ai / ha or more, 106g ai / ha or more, 107g ai / ha or more, 108g ai / ha or more, 109g ai / ha or more, 110g ai / ha or more, 111g ai / ha or more, 112g ai / ha or more ai / ha or more, 113g ai / ha or more, 114g ai / ha or more, 115g ai / ha or more, 116g ai / ha or more, 117g ai / ha or more, 118g ai / ha or more, or 119g ai / ha or more;In the following amounts: 120g ai / ha or less, such as 119g ai / ha or less, 118g ai / ha or less, 117g ai / ha or less, 116g ai / ha or less, 115g ai / ha or less, 114g ai / ha or less, 113g ai / ha or less, 112g ai / ha or less, 111g ai / ha or less, 110g ai / ha or less, 109g ai / ha or less, 108g ai / ha or less, 107g ai / ha or less, 106g ai / ha or less, 105g ai / ha or less, 104g ai / ha or less, 103g ai / ha or less, 102g ai / ha or less, 101g ai / ha or less, 100g ai / ha or less, 95g ai / ha or less g ai / ha or less, 90g ai / ha or less, 85g ai / ha or less, 80g ai / ha or less, 75g ai / ha or less, 70g ai / ha or less, 65g ai / ha or less, 60g ai / ha or less, 55g ai / ha or less, 50g ai / ha or less, 45g ai / ha or less, 40g ai / ha or less, 38g ai / ha or less, 36g ai / ha or less, 34g ai / ha or less, 32g ai / ha or less, 30g ai / ha or less, 28g ai / ha or less, 26g ai / ha or less, 24g ai / ha or less, 22g ai / ha or less, 20g ai / ha or less, 19g ai / ha or less, 18g ai / ha or less, 17g ai / ha or less g ai / ha, 10-150g ai / ha, 11-16g ai / ha, 12-17g ai / ha, 13-18g ai / ha, 14-16g ai / ha, 15-18g ai / ha, 16-17g ai / ha, 17-18g ai / ha, 18-19g ai / ha, 20-21g ai / ha, 22-23g ai / ha, 24-25g ai / ha, 26-27g ai / ha, 28-29g ai / ha, 29-30g ai / ha, 30-31g ai / ha, 31-32g ai / ha, 32-33g ai / ha, 33-34g ai / ha, 35-36g ai / ha, 37-38g ai / ha, 38-39g ai / ha, 39-40g ai / ha, 40-45g ai / ha, 41-42g ai / ha, ai / ha, 20-100g ai / ha, 24-105g ai / ha, or 28-115g ai / ha. ; Flupyralid
[0243] The compositions and methods of the present disclosure may include flupyralidone or an agriculturally acceptable salt or ester thereof. Flupyralidone-methyl sodium, shown below, is a sulfonylurea that is used, for example, for post-emergence control of grass and broadleaf weeds in cereals. Flupyralidone and methods for preparing flupyralidone are known in the art. Its herbicidal activity is described in The Pesticide Manual, Seventeenth Edition, 2016.
[0244] Flupyralid may be applied to vegetation or areas adjacent to vegetation or to soil or water in an amount sufficient to induce a herbicidal effect to prevent the emergence or growth of vegetation. In some aspects, fluazifop-sodium is applied to vegetation or to an area adjacent to vegetation or to soil or water in an amount to prevent emergence or growth of vegetation: 2.5 g ai / ha or more, such as 2.6 g ai / ha or more, 2.7 g ai / ha or more, 2.8 g ai / ha or more, 2.9 g ai / ha or more, 3.0 g ai / ha or more, 3.2 g ai / ha or more, 3.4 g ai / ha or more, 3.6 g ai / ha or more, 3.8 g ai / ha or more, 4 g ai / ha or more, 4.2 g ai / ha or more, 4.4 g ai / ha or more, 4.6 g ai / ha or more, 4.8 g ai / ha or more, 5 g ai / ha or more, 5.2 g ai / ha or more, 5.4 g ai / ha or more, 5.6 g ai / ha or more, 5.8 g ai / ha or more, 6 g ai / ha or more, 6.2 g ai / ha or more. or more, 6.4g ai / ha or more, 6.6g ai / ha or more, 6.8g ai / ha or more, 7g ai / ha or more, 7.2ai / ha or more, 7.4g ai / ha or more, 7.6g ai / ha or more, 8g ai / ha or more, 8.2g ai / ha or more, 8.4ai / ha or more, 8.6g ai / ha or more, 8.8g ai / ha or more, 9g ai / ha or more, 9.1g ai / ha or more, 9.2g ai / ha or more, 9.3g ai / ha or more, 9.4g ai / ha or more, 9.5g ai / ha or more, 9.6g ai / ha or more, 9.7g ai / ha or more, 9.8g ai / ha or more, or 9.9g ai / ha or more; in the following amounts: 10g ai / ha or less, such as 9.9g ai / ha or less, 9.8g ai / ha or less, 9.7g ai / ha or less, 9.6g ai / ha or less, 9.5g ai / ha or less, 9.4g ai / ha or less, 9.3g ai / ha or less, 9.2g ai / ha or less, 9.1g ai / ha or less, 9g ai / ha or less, 8.8g ai / ha or less, 8.6g ai / ha or less, 8.4g ai / ha or less, 8.2g ai / ha or less, 8g ai / ha or less, 7.8g ai / ha or less, 7.6g ai / ha or less, 7.4g ai / ha or less, 7.2g ai / ha or less, 7g ai / ha or less, 6.8g ai / ha or less, 6.6g ai / ha or less, 6.4g ai / ha or less, 6.2g ai / ha or less, 6g ai / ha or less, 5.8g ai / ha or less, 5.6g ai / ha or less, 5.4g ai / ha or less, 5.2g ai / ha or less, 5g ai / ha or less, 4.8g ai / ha or less, 4.6g ai / ha or less, 4.4g ai / ha or less, 4.2g ai / ha or less, 4g ai / ha or less, 3.8g ai / ha or less, 3.6g ai / ha or less, 3.4g ai / ha or less, 3.2g ai / ha or less, 3g ai / ha or less, 2.9g ai / ha or less, 2.8g ai / ha or less, 2.7g ai / ha or less ai / ha or less, or 2.6g ai / ha or less; or in an amount ranging from any of the above minimum values to any of the above maximum values, such as 2.5-10g ai / ha, 2.5-9.4g ai / ha, 2.6-9g ai / ha, 2.7-10g ai / ha, 2.8-9.4g ai / ha, 3-8.8g ai / ha, 3.2-7.2g ai / ha, 3.4-8.6g ai / ha, 3.6-10g ai / ha, 3.8-9.5g ai / ha, 4-8.8g ai / ha, 4.4-7g ai / ha, 4.6-6.8g ai / ha, or 5-9.5g ai / ha. Foramsulfuron
[0245] Compositions and methods of the present disclosure may include foramsulfuron or an agriculturally acceptable salt or ester thereof. Foramsulfuron, as shown below, is a sulfonylurea that provides post-emergence control of grass weeds and broadleaf weeds in, for example, corn. Foramsulfuron and methods for preparing foramsulfuron are known in the art. Its herbicidal activity is described in The Pesticide Manual, Seventeenth Edition, 2016.
[0246] Foramsulfuron may be applied to vegetation or areas adjacent to vegetation or to soil or water in an amount sufficient to induce a herbicidal action to prevent the emergence or growth of vegetation. In some aspects, foramsulfuron is applied to vegetation or an area adjacent to vegetation or to soil or water in an amount to prevent emergence or growth of vegetation: 22.5 g ai / ha or more, such as 23 g ai / ha or more, 24 g ai / ha or more, 25 g ai / ha or more, 26 g ai / ha or more, 28 g ai / ha or more, 30 g ai / ha or more, 32 g ai / ha or more, 34 g ai / ha or more, 35 g ai / ha or more, 36 g ai / ha or more, 38 g ai / ha or more, 40 g ai / ha or more, 42 g ai / ha or more, 44 g ai / ha or more, 46 g ai / ha or more, 48 g ai / ha or more, 50 g ai / ha or more, 51 g ai / ha or more, 52 g ai / ha or more, 53 g ai / ha or more, 54 g ai / ha or more, 55 g ai / ha or more, in the following amounts: 59g ai / ha or less, such as 58g ai / ha or less, 57g ai / ha or less, 56g ai / ha or less, 55g ai / ha or less, 54g ai / ha or less, 53g ai / ha or less, 52g ai / ha or less, 51g ai / ha or less, 50g ai / ha or less, 48g ai / ha or less, 46g ai / ha or less, 44gai / ha or less, 42g ai / ha or less, 40g ai / ha or less, 38g ai / ha or less, 36g ai / ha or less, 35g ai / ha or less, 34g ai / ha or less, 32g ai / ha or less, 30g ai / ha or less. g ai / ha or less, 28 g ai / ha or less, 26 g ai / ha or less, 25 g ai / ha or less, 24 g ai / ha or less, or 23 g ai / ha or less; or in an amount ranging from any of the above minimum values to any of the above maximum values, such as 22.5-59 g ai / ha, 23-51 g ai / ha, 25-38 g ai / ha, 26-57 g ai / ha, 28-48 g ai / ha, 30-58 g ai / ha, 30-50 g ai / ha, 32-55 g ai / ha, 34-57 g ai / ha, or 35-58 g ai / ha. Halosulfuron-methyl
[0247] Compositions and methods of the present disclosure may include chlorpyrifos methyl or an agriculturally acceptable salt or ester thereof. Chlorpyrifos methyl-methyl, as shown below, is a sulfonylurea with demonstrated activity in controlling annual broadleaf weeds and sedge nutgrass species in maize, sugarcane, rice, sorghum, nuts, and turf. Chlorpyrifos methyl and methods for preparing chlorpyrifos methyl are known in the art. Its herbicidal activity is described in The Pesticide Manual, Seventeenth Edition, 2016.
[0248] Halosulfuron-methyl may be applied to vegetation or areas adjacent to vegetation or to soil or water in an amount sufficient to induce a herbicidal action to prevent the emergence or growth of vegetation. In some aspects, chlorpyrifos methyl is applied to vegetation or an area adjacent to vegetation or to soil or water in an amount to prevent emergence or growth of vegetation: 4.375 g ai / ha or more, such as 4.75 g ai / ha or more, 5 g ai / ha or more, 6 g ai / ha or more, 7 g ai / ha or more, 8 g ai / ha or more, 9 g ai / ha or more, 10 g ai / ha or more, 15 g ai / ha or more, 20 g ai / ha or more, 25 g ai / ha or more, 30 g ai / ha or more, 35 g ai / ha or more, 40 g ai / ha or more, 45 g ai / ha or more, 50 g ai / ha or more, 55 g ai / ha or more, 60 g ai / ha or more, 65 g ai / ha or more, 70 g ai / ha or more, 75 g ai / ha or more, 80 g ai / ha or more, 85 g ai / ha or more. g ai / ha or more, 90g ai / ha or more, 95g ai / ha or more, 100g ai / ha or more, 105g ai / ha or more, 110g ai / ha or more, 115g ai / ha or more, 120g ai / ha or more, 122g ai / ha or more, 124g ai / ha or more, 126g ai / ha or more, 128g ai / ha or more, 130g ai / ha or more, 131g ai / ha or more, 132g ai / ha or more, 133g ai / ha or more, 134g ai / ha or more, 135g ai / ha or more, 136g ai / ha or more, 137g ai / ha or more, 138g ai / ha or more, or 139g ai / ha or more;In the following amounts: 139g ai / ha or less, such as 138g ai / ha or less, 137g ai / ha or less, 136g ai / ha or less, 135g ai / ha or less, 134g ai / ha or less, 133g ai / ha or less, 132g ai / ha or less, 131g ai / ha or less, 130g ai / ha or less, 129g ai / ha or less, 128g ai / ha or less, 126g ai / ha or less, 124g ai / ha or less, 122g ai / ha or less, 120g ai / ha or less, 115g ai / ha or less, 110g ai / ha or less, 105g ai / ha or less, 100g ai / ha or less, 95g ai / ha or less, 90g ai / ha or less. g ai / ha or less, 85g ai / ha or less, 80g ai / ha or less, 75g ai / ha or less, 70g ai / ha or less, 65g ai / ha or less, 60g ai / ha or less, 55g ai / ha or less, 50g ai / ha or less, 45g ai / ha or less, 40g ai / ha or less, 35g ai / ha or less, 30g ai / ha or less, 25g ai / ha or less, 20g ai / ha or less, 15g ai / ha or less, 10g ai / ha or less, 9g ai / ha or less, 8g ai / ha or less, 7g ai / ha or less, 6g ai / ha or less, 5g ai / ha or less, 4.75g ai / ha or less, or 4.5g ai / ha or less. ai / ha or less; or in an amount ranging from any of the above minimum values to any of the above maximum values, such as 4.375-140g ai / ha, 4.5-120g ai / ha, 4.75-100g ai / ha, 5-95g ai / ha, 5-131g ai / ha, 6-80g ai / ha, 7-130g ai / ha, 8-122g ai / ha, 9-75g ai / ha, 10-139g ai / ha, 15-90g ai / ha, 20-124g ai / ha, 25-110g ai / ha, or 25-75g ai / ha. ; Iodosulfuron-methyl
[0249] The compositions and methods of the present disclosure may include iodosulfuron-methyl or an agriculturally acceptable salt or ester thereof. Iodosulfuron-methyl-sodium, as shown below, is a sulfonylurea that provides post-emergence control of grass and broadleaf weeds in, for example, winter, spring, and durum wheat, triticale, rye, and spring barley. Iodosulfuron-methyl and methods for preparing iodosulfuron-methyl are known in the art. Its herbicidal activity is described in The Pesticide Manual, Seventeenth Edition, 2016.
[0250] Iodosulfuron-methyl may be applied to vegetation or areas adjacent to vegetation or to soil or water in an amount sufficient to induce a herbicidal action to prevent the emergence or growth of vegetation. In some aspects, iodosulfuron-methyl is applied to vegetation or to an area adjacent to vegetation or to soil or water in an amount of 0.1 g ai / ha or more, such as 0.2 g ai / ha or more, 0.3 g ai / ha or more, 0.4 g ai / ha or more, 0.5 g ai / ha or more, 0.6 g ai / ha or more, 0.7 g ai / ha or more, 0.8 g ai / ha or more, 0.9 g ai / ha or more, 1 g ai / ha or more, 1.1 g ai / ha or more, 1.2 g ai / ha or more, 1.3 g ai / ha or more, 1.4 g ai / ha or more, 1.5 g ai / ha or more, 1.6 g ai / ha or more, 1.7 g ai / ha or more, 1.8 g ai / ha or more, 1.9 g ai / ha or more, 2.0 g ai / ha or more. , 2.1g ai / ha or more, 2.2g ai / ha or more, 2.3g ai / ha or more, 2.3g ai / ha or more, 2.4g ai / ha or more, 2.5g ai / ha or more, 2.6g ai / ha or more, 2.7g ai / ha or more, 2.8g ai / ha or more, 2.9g ai / ha or more, 3.0g ai / ha or more, 3.2g ai / ha or more, 3.4g ai / ha or more, 3.6g ai / ha or more, 3.8g ai / ha or more, 4g ai / ha or more, 4.2g ai / ha or more, 4.4g ai / ha or more, 4.6g ai / ha or more, 4.8g ai / ha or more, 5g ai / ha or more, 5.2g ai / ha or more, 5.4g ai / ha or more, 5.6g ai / ha or more, 5.8g ai / ha or more g ai / ha or more, 6g ai / ha or more, 6.2g ai / ha or more, 6.4g ai / ha or more, 6.6g ai / ha or more, 6.8g ai / ha or more, 7g ai / ha or more, 7.2g ai / ha or more, 7.4g ai / ha or more, 7.6g ai / ha or more, 8g ai / ha or more, 8.2g ai / ha or more, 8.4ai / ha or more, 8.6g ai / ha or more, 8.8g ai / ha or more, 9g ai / ha or more, 9.1g ai / ha or more, 9.2g ai / ha or more, 9.3g ai / ha or more, 9.4g ai / ha or more, 9.5g ai / ha or more, 9.in an amount as follows: 10 g ai / ha or less, such as 9.9 g ai / ha or less, 9.8 g ai / ha or less, 9.7 g ai / ha or less, 9.6 g ai / ha or less, 9.5 g ai / ha or less, 9.4 g ai / ha or less, 9.3 g ai / ha or less, 9.2 g ai / ha or less, 9.1 g ai / ha or less, 9 g ai / ha or less, 8.8 g ai / ha or less, 8.6 g ai / ha or less, 8.4 g ai / ha or less, 8.2 g ai / ha or less, 8 g ai / ha or less, 7.8 g ai / ha or less, 7.6 g ai / ha or less, 7.4 g ai / ha or less. g ai / ha or less, 7.2 g ai / ha or less, 7 g ai / ha or less, 6.8 g ai / ha or less, 6.6 g ai / ha or less, 6.4 g ai / ha or less, 6.2 g ai / ha or less, 6 g ai / ha or less, 5.8 g ai / ha or less, 5.6 g ai / ha or less, 5.4 g ai / ha or less, 5.2 g ai / ha or less, 5 g ai / ha or less, 4.8 g ai / ha or less, 4.6 g ai / ha or less, 4.4 g ai / ha or less, 4.2 g ai / ha or less, 4 g ai / ha or less, 3.8 g ai / ha or less, 3.6 g ai / ha or less, 3.4 g ai / ha or less, 3.2 g ai / ha or less, 3 g ai / ha or less, 2.9 g ai / ha or less, g ai / ha or less, 2.8 g ai / ha or less, 2.7 g ai / ha or less, 2.6 g ai / ha or less, 2.5 g ai / ha or less, 2.4 g ai / ha or less, 2.3 g ai / ha or less, 2.2 g ai / ha or less, 2.1 g ai / ha or less, 2.0 g ai / ha or less, 1.9 g ai / ha or less, 1.8 g ai / ha or less, 1.7 g ai / ha or less, 1.6 g ai / ha or less, 1.5 g ai / ha or less, 1.4 g ai / ha or less, 1.3 g ai / ha or less, 1.2 g ai / ha or less, 1.1 g ai / ha or less, 1 g ai / ha or less, 0.9 g ai / ha or less, 0.8 g ai / ha or less, 0.7 g ai / ha or less ai / ha or less, 0.6g ai / ha or less, 0.5g ai / ha or less, 0.4g ai / ha or less, 0.3g ai / ha or less, or 0.2 g ai / ha or less; or in an amount ranging from any of the above minimum values to any of the above maximum values, such as 0.1-10 g ai / ha, 0.4-8.8 g ai / ha, 1.1-6.2 g ai / ha, 1.7-7.5 g ai / ha, 1.8-9.2 g ai / ha, 1.9-9 g ai / ha, 2-6.8 g ai / ha, 2.2-9.5 g ai / ha, 2.5-10 g ai / ha, 2.8-7.6 g ai / ha, 3-9.4 g ai / ha, 3.2-7.2 g ai / ha, 3.4-10 g ai / ha, or 3.6-8 g ai / ha. Mesosulfuron
[0251] Compositions and methods of the present disclosure may include mesosulfuron or an agriculturally acceptable salt or ester thereof. Mesosulfuron-methyl, as shown below, is a sulfonylurea that provides early to mid-emergence control of grass weeds and some broadleaf weeds in, for example, winter, spring, and durum wheat, triticale, and rye. Mesosulfuron and methods for preparing mesosulfuron are known in the art. Its herbicidal activity is described in The Pesticide Manual, Seventeenth Edition, 2016.
[0252] Mesosulfuron may be applied to vegetation or areas adjacent to vegetation or to soil or water in an amount sufficient to induce a herbicidal action to prevent the emergence or growth of vegetation. In some aspects, the mesosulfuron is applied to vegetation or an area adjacent to vegetation or to soil or water in an amount to prevent emergence or growth of vegetation: 1.5 g ai / ha or more, such as 1.6 g ai / ha or more, 1.7 g ai / ha or more, 1.8 g ai / ha or more, 1.9 g ai / ha or more, 2 g ai / ha or more, 2.1 g ai / ha or more, 2.25 g ai / ha or more, 2.5 g ai / ha or more, 2.75 g ai / ha or more, 3 g ai / ha or more, 3.25 g ai / ha or more, 3.5 g ai / ha or more, 3.75 g ai / ha or more, 4 g ai / ha or more, 4.25 g ai / ha or more, 4.5 g ai / ha or more, 4.75g ai / ha or more, 5g ai / ha or more, 6g ai / ha or more, 7g ai / ha or more, 8g ai / ha or more, 9g ai / ha or more, 10g ai / ha or more, 12g ai / ha or more, 14g ai / ha or more, 16g ai / ha or more, 18g ai / ha or more, 20g ai / ha or more, 22g ai / ha or more, 24g ai / ha or more, 26g ai / ha or more, 28g ai / ha or more, 30g ai / ha or more, 31g ai / ha or more, 32g ai / ha or more, 33g ai / ha or more, 34g ai / ha or more, 35g ai / ha or more, 36g ai / ha or more, 37g ai / ha or more, 38g ai / ha or more, 39g ai / ha or more, 40g ai / ha or more, 41g ai / ha or more in the following amounts: 45g ai / ha or less, such as 44g ai / ha or less, 43g ai / ha or less, 42g ai / ha or less, 41g ai / ha or less, 40g ai / ha or less, 39g ai / ha or less, 38g ai / ha or less, 37g ai / ha or less, 36g ai / ha or less, 35g ai / ha or less, 34g ai / ha or less, 33g ai / ha or less, 32g ai / ha or less, 31g ai / ha or less, 30g ai / ha or less, 28g ai / ha or less, 26g ai / ha or less, 24g ai / ha or less, 22g ai / ha or less, 20g g ai / ha or less, 18g ai / ha or less, 16g ai / ha or less, 14g ai / ha or less, 12g ai / ha or less, 10g ai / ha or less, 9g ai / ha or less, 8g ai / ha or less, 7g ai / ha or less, 6g ai / ha or less, 5g ai / ha or less, 4.75g ai / ha or less, 4.5g ai / ha or less, 4.25g ai / ha or less, 4g ai / ha or less, 3.75g ai / ha or less, 3.5g ai / ha or less, 3.25g ai / ha or less, 3g ai / ha or less, 2.75g ai / ha or less, 2.5g ai / ha or less, 2.25g ai / ha or less, 2.1g ai / ha or less, 2g ai / ha or less, 1.9g ai / ha or less, 1.8g ai / ha or less, 1.7g ai / ha or less, 1.6g ai / ha or less; or in an amount ranging from any of the above minimum values to any of the above maximum values, such as 1.5-45g ai / ha, 1.6-42g ai / ha, 1.5-40g ai / ha, 1.7-43g ai / ha, 1.8-35g ai / ha, 2-37g ai / ha, 2.25-41g ai / ha, 2.5-32g ai / ha, 2.75-45g ai / ha, 3-40g ai / ha, 3-33g ai / ha, 3-24g ai / ha, 3.5-45g ai / ha, or 4-39g ai / ha. Metsulfuron-methyl
[0253] The compositions and methods of the present disclosure may include metsulfuron-methyl or an agriculturally acceptable salt or ester thereof. Metsulfuron-methyl, as shown below, is a sulfonylurea that controls grass and broadleaf weeds in, for example, wheat, barley, rice, oats, and triticale. Metsulfuron-methyl and methods for preparing metsulfuron-methyl are known in the art. Its herbicidal activity is described in The Pesticide Manual, Seventeenth Edition, 2016.
[0254] Metsulfuron-methyl may be applied to vegetation or areas adjacent to vegetation or to soil or water in an amount sufficient to induce a herbicidal effect to prevent the emergence or growth of vegetation. In some aspects, metsulfuron-methyl is applied to vegetation or an area adjacent to vegetation or to soil or water in an amount of 1 g ai / ha or more to prevent emergence or growth of vegetation, such as 1.1 g ai / ha or more, 1.2 g ai / ha or more, 1.25 g ai / ha or more, 1.3 g ai / ha or more, 1.4 g ai / ha or more, 1.5 g ai / ha or more, 1.6 g ai / ha or more, 1.7 g ai / ha or more, 1.8 g ai / ha or more, 1.9 g ai / ha or more, 2 g ai / ha or more, 2.1 g ai / ha or more, 2.2 g ai / ha or more, 2.3 g ai / ha or more, 2.4 g ai / ha or more, 2.5 g ai / ha or more, 2.6 g ai / ha or more, 2.7 g ai / ha or more, 2.8 g ai / ha or more, 2.9 g ai / ha or more. G ai / ha or more, 3g ai / ha or more, 3.2g ai / ha or more, 3.4g ai / ha or more, 3.6g ai / ha or more, 3.8g ai / ha or more, 4g ai / ha or more, 4.2g ai / ha or more, 4.4g ai / ha or more, 4.6g ai / ha or more, 4.8g ai / ha or more, 5g ai / ha or more, 5.2g ai / ha or more, 5.4g ai / ha or more, 5.6g ai / ha or more, 5.8g ai / ha or more, 6g ai / ha or more, 6.2g ai / ha or more, 6.4g ai / ha or more, 6.6g ai / ha or more, 6.8g ai / ha or more, 7g ai / ha or more, 7.2g ai / ha or more, 7.4g ai / ha or more, 7.6g ai / ha or more, 7.8g ai / ha or more, 8g ai / ha or more g ai / ha or more, 8.2 g ai / ha or more, 8.4 g ai / ha or more, 8.6 g ai / ha or more, 8.8 g ai / ha or more, 9 g ai / ha or more, 9.2 g ai / ha or more, 9.4 g ai / ha or more, 9.6 g ai / ha or more, 9.8 g ai / ha or more, 10 g ai / ha or more, 10.2 g ai / ha or more, 10.4 g ai / ha or more, 10.6 g ai / ha or more, 10.8 g ai / ha or more, 11 g ai / ha or more, 11.1 g ai / ha or more, 11.2 g ai / ha or more, 11.3g ai / ha or more, 11.4g ai / ha or more, 11.5g ai / ha or more, 11.6g ai / ha or more, 11.7g ai / ha or more, 11.8g ai / ha or more, or 11.9g ai / ha or more; in an amount of 12g ai / ha or less, such as 11.9g ai / ha or less, 11.8g ai / ha or less, 11.7g ai / ha or less, 11.6g ai / ha or less, 11.5g ai / ha or less, 11.4g ai / ha or less, 11.3g ai / ha or less, 11.2g ai / ha or less, 11.1g ai / ha or less, 11g ai / ha or less, 10.8g ai / ha or less, 10.6g ai / ha or less, 10.4g ai / ha or less. g ai / ha or less, 10.2 g ai / ha or less, 10 g ai / ha or less, 9.8 g ai / ha or less, 9.6 g ai / ha or less, 9.4 g ai / ha or less, 9.2 g ai / ha or less, 9 g ai / ha or less, 8.8 g ai / ha or less, 8.6 g ai / ha or less, 8.4 g ai / ha or less, 8.2 g ai / ha or less, 8 g ai / ha or less, 7.8 g ai / ha or less, 7.6 g ai / ha or less, 7.4 g ai / ha or less, 7.2 g ai / ha or less, 7 g ai / ha or less, 6.8 g ai / ha or less, 6.6 g ai / ha or less, 6.4 g ai / ha or less, 6.2 g ai / ha or less, 6 g ai / ha or less, 5.8 g ai / ha or less, g ai / ha or less, 5.6g ai / ha or less, 5.4g ai / ha or less, 5.2g ai / ha or less, 5g ai / ha or less, 4.8g ai / ha or less, 4.6g ai / ha or less, 4.4g ai / ha or less, 4.2g ai / ha or less, 4g ai / ha or less, 3.8g ai / ha or less, 3.6g ai / ha or less, 3.4g ai / ha or less, 3.2g ai / ha or less, 3g ai / ha or less, 2.9g ai / ha or less, 2.8g ai / ha or less, 2.7g ai / ha or less, 2.6g ai / ha or less, 2.5g ai / ha or less, 2.4g ai / ha or less, 2.3g ai / ha or less, 2.2g ai / ha or less, 2.1g ai / ha or less ai / ha or less, 2g ai / ha or less, 1.9g ai / ha or less, 1.8g ai / ha, 1.7g ai / ha or less, 1.6g ai / ha or less, 1.5g ai / ha or less, 1.4g ai / ha or less, 1.3g ai / ha or less, 1.25g ai / ha or less, 1.2g ai / ha or less, or 1.1g ai / ha or less; or in an amount ranging from any of the above minimum values to any of the above maximum values, such as 1-12g ai / ha, 1-10g ai / ha, 1.1-9.4g ai / ha, 1.25-8.2g ai / ha, 1.25-11g ai / ha, 1.3-7g ai / ha, 1.4-5.8g ai / ha, 1.5-12g ai / ha, 1.5-10.4g ai / ha, 1.5-8.8g ai / ha, 2-11.7g ai / ha, 2.2-6.4g ai / ha. ai / ha, 2.5-7.6g ai / ha, 2.8-12g ai / ha, or 3-8g ai / ha. . Nicosulfuron
[0255] Compositions and methods of the present disclosure may include nicosulfuron or an agriculturally acceptable salt or ester thereof. Nicosulfuron, as shown below, is a sulfonylurea that provides selective post-emergence control of annual grass weeds (including Setaria, Echinochloa, Digitaria, Panicum, Lysimachia, and Avena species), broadleaf weeds (including Amaranth species and crucifers), and perennial plants (such as Sorghum tsaoko and Elymus chinensis) in, for example, maize. Nicosulfuron and methods for preparing nicosulfuron are known in the art. Its herbicidal activity is described in The Pesticide Manual, Seventeenth Edition, 2016.
[0256] Nicosulfuron may be applied to vegetation or areas adjacent to vegetation or to soil or water in an amount sufficient to induce a herbicidal effect to prevent the emergence or growth of vegetation. In some aspects, nicosulfuron is applied to vegetation or to an area adjacent to vegetation or to soil or water in an amount to prevent emergence or growth of vegetation: 8.75 g ai / ha or more, such as 9 g ai / ha or more, 10 g ai / ha or more, 11 g ai / ha or more, 12 g ai / ha or more, 13 g ai / ha or more, 14 g ai / ha or more, 15 g ai / ha or more, 16 g ai / ha or more, 17 g ai / ha or more, 18 g ai / ha or more, 19 g ai / ha or more, 20 g ai / ha or more, 22 g ai / ha or more, 24 g ai / ha or more, 26 g ai / ha or more, 28 g ai / ha or more, 30 g ai / ha or more, 32 g ai / ha or more, 34 g ai / ha or more, 36 g ai / ha or more, 38 g ai / ha or more, 40 g ai / ha or more g ai / ha or more, 42g ai / ha or more, 44g ai / ha or more, 46g ai / ha or more, 48g ai / ha or more, 50g ai / ha or more, 52g ai / ha or more, 54g ai / ha or more, 56g ai / ha or more, 58g ai / ha or more, 60g ai / ha or more, 62g ai / ha or more, 64g ai / ha or more, 66g ai / ha or more, 68g ai / ha or more, or 69g ai / ha or more;In amounts such as 70 g ai / ha or less, such as 69 g ai / ha or less, 68 g ai / ha or less, 66 g ai / ha or less, 64 g ai / ha or less, 62 g ai / ha or less, 60 g ai / ha or less, 58 g ai / ha or less, 56 g ai / ha or less, 54 g ai / ha or less, 52 g ai / ha or less, 50 g ai / ha or less, 48 g ai / ha or less, 46 g ai / ha or less, 44 g ai / ha or less, 42 g ai / ha or less, 40 g ai / ha or less, 38 g ai / ha or less, 36 g ai / ha or less, 34 g ai / ha or less, 32 g ai / ha or less, 30 g ai / ha or less, 28 g ai / ha or less, 26 g ai / ha or less. g ai / ha or less, 24g ai / ha or less, 22g ai / ha or less, 20g ai / ha or less, 19g ai / ha or less, 18g ai / ha or less, 17g ai / ha or less, 16g ai / ha or less, 15g ai / ha or less, 14g ai / ha or less, 13g ai / ha or less, 12g ai / ha or less, 11g ai / ha or less, 10g ai / ha or less, or 9g ai / ha or less; or in an amount ranging from any of the foregoing minimum values to any of the foregoing maximum values, such as 8.75-70g ai / ha, 9-78g ai / ha, 10-50g ai / ha, 12-76g ai / ha, 14-44g ai / ha, 15-58g ai / ha, 18-65g ai / ha, ai / ha, 20-45g ai / ha, 22-60g ai / ha, 26-56g ai / ha, or 30-70g ai / ha. ; Pyrifasulfuron
[0257] Compositions and methods of the present disclosure may include pyrimidinesulfuron or an agriculturally acceptable salt or ester thereof. Pyrimidinesulfuron, as shown below, is a sulfonylurea that provides early post-emergence control of annual and perennial broadleaf weeds and sedges in, for example, rice, cereals, pasture, and sugarcane. Pyrimidinesulfuron and methods for preparing pyrimidinesulfuron are known in the art. Its herbicidal activity is described, for example, in The Pesticide Manual, Seventeenth Edition, 2016.
[0258] Pyrimidinesulfuron-methyl may be applied to vegetation or areas adjacent to vegetation or to soil or water in an amount sufficient to induce a herbicidal action to prevent the emergence or growth of vegetation. In some aspects, pyrimidinesulfuron-methyl is applied to vegetation or an area adjacent to vegetation or to soil or water in an amount to prevent emergence or growth of vegetation: 7.5 g ai / ha or more, such as 8 g ai / ha or more, 9 g ai / ha or more, 10 g ai / ha or more, 11 g ai / ha or more, 12 g ai / ha or more, 13 g ai / ha or more, 14 g ai / ha or more, 15 g ai / ha or more, 16 g ai / ha or more, 17 g ai / ha or more, 18 g ai / ha or more, 19 g ai / ha or more, 20 g ai / ha or more, 22 g ai / ha or more, 24 g ai / ha or more, 26 g ai / ha or more, 28 g ai / ha or more, 30 g ai / ha or more, 32 g ai / ha or more, 34 g ai / ha or more, 36 g ai / ha or more, 38 g ai / ha or more. g ai / ha or more, 40g ai / ha or more, 42g ai / ha or more, 44g ai / ha or more, 46g ai / ha or more, 48g ai / ha or more, 50g ai / ha or more, 52g ai / ha or more, 54g ai / ha or more, 56g ai / ha or more, 58g ai / ha or more, 60g ai / ha or more, 62g ai / ha or more, 64g ai / ha or more, 66g ai / ha or more, 68g ai / ha or more, 70g ai / ha or more, 71g ai / ha or more, 72g ai / ha or more, 73g ai / ha or more, or 74g ai / ha or more;In the following amounts: 75g ai / ha or less, such as 74g ai / ha or less, 72g ai / ha or less, 70g ai / ha or less, 68g ai / ha or less, 66g ai / ha or less, 64g ai / ha or less, 62g ai / ha or less, 60g ai / ha or less, 58g ai / ha or less, 56g ai / ha or less, 54g ai / ha or less, 52g ai / ha or less, 50g ai / ha or less, 48g ai / ha or less, 46g ai / ha or less, 44g ai / ha or less, 42g ai / ha or less, 40g ai / ha or less, 38g ai / ha or less, 36g ai / ha or less, 34g ai / ha or less, 32g ai / ha or less, 30g or less, 28g ai / ha or less, 26g ai / ha or less, 24g ai / ha or less, 22g ai / ha or less, 20g ai / ha or less, 19g ai / ha or less, 18g ai / ha or less, 17g ai / ha or less, 16g ai / ha or less, 15g ai / ha or less, 14g ai / ha or less, 13g ai / ha or less, 12g ai / ha or less, 11g ai / ha or less, 10g ai / ha or less, 9g ai / ha or less, or 8g ai / ha or less; or in an amount ranging from any of the foregoing minimum values to any of the foregoing maximum values, such as 7.5-75g ai / ha, 7.5-60g ai / ha, 8-58g ai / ha, 9-42g ai / ha, 10-70g ai / ha ai / ha, 10-56g ai / ha, 11-40g ai / ha, 13-64g ai / ha, 15-75g ai / ha, 17-46gai / ha, 20-65g ai / ha, 20-52g ai / ha, 22-48g ai / ha, or 24-74gai / ha. ; Sulfosulphonyl
[0259] Compositions and methods of the present disclosure may include sulfasulfuron or an agriculturally acceptable salt or ester thereof. Sulfasulfuron, as shown below, is a sulfonylurea that provides post-emergence control of most annual and perennial grass weeds and several broadleaf weeds in maize, tomatoes, and potatoes at 15 g / ha. Sulfasulfuron and methods for preparing sulfasulfuron are known in the art. Its herbicidal activity is described in The Pesticide Manual, Seventeenth Edition, 2016.
[0260] Sulfosulphonate may be applied to vegetation or areas adjacent to vegetation or to soil or water in an amount sufficient to induce a herbicidal effect to prevent the emergence or growth of vegetation. In some aspects, sulfasulfuron-methyl is applied to vegetation or to an area adjacent to vegetation or to soil or water in an amount of 5 g ai / ha or more, such as 5.5 g ai / ha or more, 6 g ai / ha or more, 7 g ai / ha or more, 7.5 g ai / ha or more, 8 g ai / ha or more, 9 g ai / ha or more, 10 g ai / ha or more, 12 g ai / ha or more, 14 g ai / ha or more, 16 g ai / ha or more, 18 g ai / ha or more, 20 g ai / ha or more, 22 g ai / ha or more, 24 g ai / ha or more, 26 g ai / ha or more, 27 g ai / ha or more, 28 g ai / ha or more, 30 g ai / ha or more, 32 g ai / ha or more, 34 g ai / ha or more, 36 g ai / ha or more, 38 g ai / ha or more, 40 g ai / ha or more. 4g ai / ha or more, 42g ai / ha or more, 44g ai / ha or more, 46g ai / ha or more, 48g ai / ha or more, 50g ai / ha or more, 52g ai / ha or more, 54g ai / ha or more, 56g ai / ha or more, 58g ai / ha or more, 60g ai / ha or more, 62g ai / ha or more, 64g ai / ha or more, 66g ai / ha or more, 68g ai / ha or more, 69g ai / ha or more, 70g ai / ha or more, 71g ai / ha or more, 72g ai / ha or more, 73g ai / ha or more, or 74g ai / ha or more;In the following amounts: 75g ai / ha or less, such as 74g ai / ha or less, 73g ai / ha or less, 72g ai / ha or less, 71g ai / ha or less, 70g ai / ha or less, 69g ai / ha or less, 68g ai / ha or less, 66g ai / ha or less, 64g ai / ha or less, 62g ai / ha or less, 60g ai / ha or less, 58g ai / ha or less, 56g ai / ha or less, 54g ai / ha or less, 52g ai / ha or less, 50g ai / ha or less, 48g ai / ha or less, 46g ai / ha or less, 44g ai / ha or less, 42g ai / ha or less, 40g ai / ha or less, 38g ai / ha or less. g ai / ha or less, 36 g ai / ha or less, 34 g ai / ha or less, 32 g ai / ha or less, 30 g ai / ha or less, 28 g ai / ha or less, 27 g ai / ha or less, 26 g ai / ha or less, 24 g ai / ha or less, 22 g ai / ha or less, 20 g ai / ha or less, 18 g ai / ha or less, 16 g ai / ha or less, 14 g ai / ha or less, 12 g ai / ha or less, 10 g ai / ha or less, 9 g ai / ha or less, 8 g ai / ha or less, 7.5 g ai / ha or less, 7 g ai / ha or less, 6 g ai / ha or less, 5.5 g ai / ha or less, or 5 g ai / ha or less; or in an amount ranging from any of the foregoing minimum values to any of the foregoing maximum values, such as 5-75 g ai / ha, 7.5-70g ai / ha, 9-64g ai / ha, 18-69g ai / ha, 27-36gai / ha, 5.5-66g ai / ha, 14-18g ai / ha, 27-69g ai / ha, 7-38g ai / ha, 12-52g ai / ha, 9-44gai / ha, 10-38g ai / ha, 16-75g ai / ha, or 20-48g ai / ha. ; Sulfonylsulfuron
[0261] The compositions and methods of the present disclosure may include sulfonylsulfuron or an agriculturally acceptable salt or ester thereof. Sulfonylsulfuron, as shown below, is a sulfonylurea that provides control of annual broadleaf weeds and grass weeds, such as in cereals. Sulfonylsulfuron and methods for preparing sulfonylsulfuron are known in the art. Its herbicidal activity is described in The Pesticide Manual, Seventeenth Edition, 2016.
[0262] Sulfonylsulfuron may be applied to vegetation or areas adjacent to vegetation or to soil or water in an amount sufficient to induce a herbicidal action to prevent the emergence or growth of vegetation. In some aspects, sulfosulfuron is applied to vegetation or to an area adjacent to vegetation or to soil or water in an amount to prevent emergence or growth of vegetation: 4.375 g ai / ha or more, such as 4.75 g ai / ha or more, 5 g ai / ha or more, 6 g ai / ha or more, 7 g ai / ha or more, 8 g ai / ha or more, 9 g ai / ha or more, 10 g ai / ha or more, 12 g ai / ha or more, 14 g ai / ha or more, 16 g ai / ha or more, 18 g ai / ha or more, 20 g ai / ha or more, 22 g ai / ha or more, 24 g ai / ha or more, 26 g ai / ha or more, 28 g ai / ha or more, 30 g ai / ha or more, 32 g ai / ha or more, 34 g ai / ha or more, 36 g ai / ha or more, 38 g ai / ha or more, 40 g ai / ha or more. g ai / ha or more, 42g ai / ha or more, 44g ai / ha or more, 46g ai / ha or more, 48g ai / ha or more, 50g ai / ha or more, 52g ai / ha or more, 54g ai / ha or more, 56g ai / ha or more, 58g ai / ha or more, 60g ai / ha or more, 62g ai / ha or more, 64g ai / ha or more, 66g ai / ha or more, 68g ai / ha or more, 70g ai / ha or more, 71g ai / ha or more, 72g ai / ha or more, 73g ai / ha or more, or 74g ai / ha or more;In the following amounts: 75g ai / ha or less, such as 74g ai / ha or less, 73g ai / ha or less, 72g ai / ha or less, 71g ai / ha or less, 70g ai / ha or less, 68g ai / ha or less, 66g ai / ha or less, 64g ai / ha or less, 62g ai / ha or less, 60g ai / ha or less, 58g ai / ha or less, 56g ai / ha or less, 54g ai / ha or less, 52g ai / ha or less, 50g ai / ha or less, 48g ai / ha or less, 46g ai / ha or less, 44g ai / ha or less, 42g ai / ha or less, 40g ai / ha or less, 38g ai / ha or less, 36g ai / ha or less, 34g ai / ha or less. or less, 32g ai / ha or less, 30g ai / ha or less, 28g ai / ha or less, 26g ai / ha or less, 24g ai / ha or less, 22g ai / ha or less, 20g ai / ha or less, 18g ai / ha or less, 16g ai / ha or less, 14g ai / ha or less, 12g ai / ha or less, 10g ai / ha or less, 9g ai / ha or less, 8g ai / ha or less, 7g ai / ha or less, 6g ai / ha or less, 5g ai / ha or less, or 4.75g ai / ha or less, or 4.5g ai / ha or less; or in an amount ranging from any of the foregoing minimum values to any of the foregoing maximum values, such as 4.375-75g ai / ha, 4.5-70g ai / ha, ai / ha, 4.75-64gai / ha, 5-75g ai / ha, 5-73g ai / ha, 5-66g ai / ha, 5-40g ai / ha, 6-75gai / ha, 7-68g ai / ha, 7-52g ai / ha, 9-44g ai / ha, 10-50g ai / ha, 16-75g ai / ha, or 20-60g ai / ha. ; Thifensulfuron-methyl
[0263] The compositions and methods of the present disclosure may include thifensulfuron-methyl or an agriculturally acceptable salt or ester thereof. Thifensulfuron-methyl, as shown below, is a sulfonylurea that provides control of annual weeds in, for example, cereals, corn, and pastures. Thifensulfuron-methyl and methods for preparing thifensulfuron-methyl are known in the art. Its herbicidal activity is described in The Pesticide Manual, Seventeenth Edition, 2016.
[0264] Thifensulfuron-methyl may be applied to vegetation or areas adjacent to vegetation or to soil or water in an amount sufficient to induce a herbicidal action to prevent the emergence or growth of vegetation. In some aspects, thifensulfuron-methyl is applied to vegetation or to an area adjacent to vegetation or to soil or water in an amount to prevent emergence or growth of vegetation: 4.4 g ai / ha or more, such as 4.5 g ai / ha or more, 4.6 g ai / ha or more, 4.7 g ai / ha or more, 4.8 g ai / ha or more, 4.9 g ai / ha or more, 5 g ai / ha or more, 5.2 g ai / ha or more, 5.4 g ai / ha or more, 5.6 g ai / ha or more, 5.8 g ai / ha or more, 6 g ai / ha or more, 6.2 g ai / ha or more, 6.4 g ai / ha or more, 6.6 g ai / ha or more, 6.8 g ai / ha or more, 7 g ai / ha or more, 7.2 g ai / ha or more, 7.4 g ai / ha or more, 7.6 g ai / ha or more, 7.8 g ai / ha or more, 8 g ai / ha or more. g ai / ha or more, 8.2 g ai / ha or more, 8.4 g ai / ha or more, 8.6 g ai / ha or more, 8.8 g ai / ha or more, 9 g ai / ha or more, 9.2 g ai / ha or more, 9.4 g ai / ha or more, 9.6 g ai / ha or more, 9.8 g ai / ha or more, 10 g ai / ha or more, 11 g ai / ha or more, 12 g ai / ha or more, 13 g ai / ha or more, 14 g ai / ha or more, 15 g ai / ha or more, 16 g ai / ha or more, 16.2 g ai / ha or more, 16.4 g ai / ha or more, 16.6 g ai / ha or more, 16.8 g ai / ha or more, 17 g ai / ha or more, 17.1 g ai / ha or more, 17.2 g ai / ha or more, 17.3 g ai / ha or more ai / ha or more, or 17.4g ai / ha or more; in the following amounts: 17.5g ai / ha or less, such as 17.4g ai / ha or less, 17.3g ai / ha or less, 17.2g ai / ha or less, 17.1g ai / ha or less, 17g ai / ha or less, 16.8g ai / ha or less, 16.6g ai / ha or less, 16.4g ai / ha or less, 16.2g ai / ha or less, 16g ai / ha or less, 15g ai / ha or less, 14g ai / ha or less, 13g ai / ha or less, 12g ai / ha or less, 11g ai / ha or less, 10g ai / ha or less, 9.8g ai / ha or less, 9.6g ai / ha or less, 9.4g ai / ha or less, 9.2g ai / ha or less, 9gai / ha or less, 8.8g ai / ha or less, 8.6g ai / ha or less, 8.4g ai / ha or less, 8.2g ai / ha or less, 8g ai / ha or less, 7.8g ai / ha or less, 7.6g ai / ha or less, 7.4g ai / ha or less, 7.2g ai / ha or less, 7g ai / ha or less, 6.8g ai / ha or less, 6.6g ai / ha or less, 6.4g ai / ha or less, 6.2g ai / ha or less, 6g ai / ha or less, 5.8g ai / ha or less, 5.6g ai / ha or less, 5.4g ai / ha or less or an amount ranging from any of the foregoing minimum values to any of the foregoing maximum values, such as 4.4-17.5g ai / ha, 4.5-16g ai / ha, 4.8-11g ai / ha, 5-17.3g ai / ha, 5-16.2g ai / ha, 5.4-13g ai / ha, 5.8-10g ai / ha, 6-12g ai / ha, 6-16g ai / ha, 7.4-17.4g ai / ha, 7.8-15g ai / ha, ai / ha, 8-15g ai / ha, or 8-17.1g ai / ha. . Bensulfuron-methyl
[0265] Compositions and methods of the present disclosure may include bensulfuron-methyl or an agriculturally acceptable salt or ester thereof. Bensulfuron-methyl, as shown below, is a sulfonylurea that provides post-emergence control of broadleaf weeds in, for example, cereal crops, including wheat, barley, oats, rye, and triticale. Bensulfuron-methyl and methods for preparing bensulfuron-methyl are known in the art. Its herbicidal activity is described in The Pesticide Manual, Seventeenth Edition, 2016.
[0266] Bensulfuron-methyl may be applied to vegetation or areas adjacent to vegetation or to soil or water in an amount sufficient to induce a herbicidal effect to prevent the emergence or growth of vegetation. In some aspects, bensulfuron-methyl is applied to vegetation or to an area adjacent to vegetation or to soil or water in an amount to prevent emergence or growth of vegetation: 3.75 g ai / ha or more, such as 4 g ai / ha or more, 4.25 g ai / ha or more, 4.5 g ai / ha or more, 4.75 g ai / ha or more, 5 g ai / ha or more, 5.25 g ai / ha or more, 5.5 g ai / ha or more, 5.75 g ai / ha or more, 6 g ai / ha or more, 7 g ai / ha or more, 7.5 g ai / ha or more, 8 g ai / ha or more, 9 g ai / ha or more, 10 g ai / ha or more, 11 g ai / ha or more, 12 g ai / ha or more, 13 g ai / ha or more, 14 g ai / ha or more, 15 g ai / ha or more, 16 g ai / ha or more, 17 g ai / ha or more, 18 g ai / ha or more. g ai / ha or more, 19 g ai / ha or more, 20 g ai / ha or more, 21 g ai / ha or more, 22 g ai / ha or more, 23 g ai / ha or more, 24 g ai / ha or more, 25 g ai / ha or more, 25.5 g ai / ha or more, 26 g ai / ha or more, 26.5 g ai / ha or more, 27 g ai / ha or more, 27.5 g ai / ha or more, 28 g ai / ha or more, 28.5 g ai / ha or more, 29 g ai / ha or more, 29.25 g ai / ha or more, 29.5 g ai / ha or more, or 29.75 g ai / ha or more; in amounts of 30 g ai / ha or less, such as 29.75 g ai / ha or less, 29.5 g ai / ha or less, 29.25 g ai / ha or less, 29 g ai / ha or more, ai / ha or less, 28.5g ai / ha or less, 28g ai / ha or less, 27.5g ai / ha or less, 27g ai / ha or less, 26.5g ai / ha or less, 26g ai / ha or less, 25g ai / ha or less, 24g ai / ha or less, 23g ai / ha or less, 22g ai / ha or less, 21g ai / ha or less, 20g ai / ha or less, 19g ai / ha or less, 18g ai / ha or less, 17g ai / ha or less, 16g ai / ha or less, 15g ai / ha or less, 14g ai / ha or less, 13g ai / ha or less, 12g ai / ha or less, 11g ai / ha or less, 10g ai / ha or less, 9g ai / ha or less, 8g ai / ha or less, 7.5g ai / ha or less, 7g ai / ha or less, 6g ai / ha or less, 5.75g ai / ha ai / ha or less, 5.5g ai / ha or less, 5.25g ai / ha or less, 5g ai / ha or less, 4.75g ai / ha or less, 4.5g ai / ha or less, 4.25g ai / ha or less, or 4g ai / ha or less; or in an amount ranging from any of the above minimum values to any of the above maximum values, such as 3.75-30g ai / ha, 4-27.5g ai / ha, 4.25-23g ai / ha, 4.5-17g ai / ha, 5-25g ai / ha, 6-29.5g ai / ha, 7-28g ai / ha, 7.5-23g ai / ha, 7.5-20g ai / ha, 9-30g ai / ha, 10-19g ai / ha, or 10-27.5g ai / ha. Synthetic auxin herbicides
[0267] In addition to the compound according to formula I, the composition may also include a synthetic auxin herbicide. Synthetic auxin herbicides mimic natural plant hormones and can inhibit cell division and growth. Synthetic auxin herbicides include phenoxy herbicides, benzoic acid herbicides, aryl picolinate herbicides, compounds according to formula I, quinolinecarboxylic acid herbicides, pyrimidinecarboxylic acid herbicides and benzothiazole herbicides, and agriculturally acceptable salts and esters thereof.
[0268] In some aspects, the composition can include a synthetic auxin herbicide selected from the group consisting of 2,4-D; 2,4-DB; 2,3,6-TBA, cyprodinil, aminopyralid, fenthionyl, chlorfenapyr, clopyralid, 2,4-dichlorprop, 2,4-dichlorprop-P, dicamba, clofopyralid (e.g., clofopyralid benzyl), fluazifop (e.g., fluazifop-butyl), clofopyralid, clofopyralid-MHE, clofopyralid (e.g., clofopyralid methyl), indolepyralid (e.g., indolepyralid cyanomethyl ester), 2-methyl-4-chloropropionic acid, 2-methyl-4-chloropropionic acid P, MCPA, MCPA-thioethyl, MCPB, picloram, quinclorac, clomeclorac, triclopyr, agriculturally acceptable salts and esters thereof, and combinations thereof. In some aspects, the synthetic auxin herbicide can include 2,4-D, MCPA, aminopyralid, clopyralid, dicamba, fluopyr-methyl, fluopyr-methyl, halopyralid, quinclorac, agriculturally acceptable salts and esters thereof, and combinations thereof.
[0269] The synthetic auxin herbicide or an agriculturally acceptable salt or ester thereof may be applied to vegetation or areas adjacent to vegetation, or to soil or water, in an amount sufficient to induce a herbicidal action to prevent the emergence or growth of vegetation. In some aspects, the synthetic auxin herbicide or an agriculturally acceptable salt or ester thereof is applied to vegetation or to an area adjacent to vegetation or to soil or water in an amount of 1 gram acid equivalent per hectare (g ai) or more, such as 1.5 g ai or more, 2 g ai or more, 2.5 g ai or more, 3 g ai or more, 3.5 g ai or more, 4 g ai or more, 4.5 g ai or more, 5 g ai or more, 6 g ai or more, 7 g ai or more, 8 g ai or more, 9 g ai or more, 10 g ai or more, 15 g ai or more, 20 g ai or more, 25 g ai or more, 30 g ai or more, 35 g ai or more, 40 g ai or more, 45 g ai or more, 50 g ai or more, 55 g ai or more, 60 g ai or more, 65 g ai or more, 70 g ai or more, 75 g ai or more, 80 g ai or more , 85g ai or more, 90g ai or more, 95g ai or more, 100g ai or more, 110g ai or more, 120g ai or more, 130g ai or more, 140g ai or more, 150g ai or more, 160g ai or more, 170g ai or more, 180g ai or more, 190g ai or more, 200g ai or more, 220g ai or more, 240g ai or more, 250g ai or more, 260g ai or more, 280g ai or more, 300g ai or more, 320g ai or more, 340g ai or more, 350g ai or more, 360g ai or more, 380g ai or more, 400g ai or more, 450g ai or more, 500g ai or more, 550g ai or more, 600g ai or more, 650g ai or more 1400g ai or more, 1450g ai or more, 1500g ai or more, 1600g ai or more, 1700g ai or more, 1800g ai or more, 1900g ai or more, 2000g ai or more, 2100g ai or more, 2200g ai or more, 2250g ai or more, 2300g ai or more, 2350g ai or more, 2400g ai or more, 2450g ai or more, 2500g ai or more, 2600g ai or more, 2700g ai or more, 2800g ai or more, 2900g ai or more, 3000g ai or more, 3100g ai or more, 3200g ai or more, 3300g ai or more, 350g ai or more, 3400g ai or more, 350g ai or more, 3600g ai or more, 3700g ai or more, 3800g ai or more, 3900g ai or more1g ai or more, 2000g ai or more, 2050g ai or more, 2100g ai or more, 2150g ai or more, 2200g ai or more, 2240g ai or more, 2250g ai or more, 2300g ai or more, 2350g ai or more, 2400g ai or more, 2450g ai or more, 2500g ai or more, 2600g ai or more, 2700g ai or more, 2750g ai or more, 2800g ai or more, 2900g ai or more, 3000g ai or more, 3050g ai or more, 3100g ai or more, 3150g ai or more, 3200g ai or more, 3250g ai or more, 3300g ai or more, 3350g ai or more, 3400g ai or more, 3450g ai or more ai or more, 3500g ai or more, 3600g ai or more, 3700g ai or more, 3750g ai or more, 3800g ai or more, 3900g ai or more, or 3950g ai or more; in the following amounts: 4000g ai or less, such as 3950g ai or less, 3900g ai or less, 3800g ai or less, 3750g ai or less, 3700g ai or less, 3600g ai or less, 3500g ai or less, 3450g ai or less, 3400g ai or less, 3350g ai or less, 3300g ai or less, 3250g ai or less, 3200g ai or less, 3150g ai or less, 3100g ai or less, 3050g ai or less 150g ai or less, 2100g ai or less, 2050g ai or less, 2000g ai or less, 1900g ai or less, 1800g ai or less, 1750g ai or less, 1700g ai or less, 1600g ai or less, 1500g ai or less, 1700g ai or less, 1600g ai or less, 1500g ai or less, 1500g ai or less, 1700g ai or less, 1600g ai or less, 1500g ai or less, 1500g ai or less, 1700g ai or less, 1600g ai or less, 1500g ai or less ai or less, 1450g ai or less, 1400g ai or less, 1350g ai or less, 1300g ai or less, 1250g ai or less, 1240g ai or less, 1200g1g ai or less, 1150g ai or less, 1100g ai or less, 1050g ai or less, 1000g ai or less, 950g ai or less, 900g ai or less, 850g ai or less, 800g ai or less, 750g ai or less, 700g ai or less, 650g ai or less, 600g ai or less, 550g ai or less, 500g ai or less, 450g ai or less, 400g ai or less, 380g ai or less, 360g ai or less, 350g ai or less, 340g ai or less, 320g ai or less, 300g ai or less, 280g ai or less, 260g ai or less, 250g ai or less, 240g ai or less, 220g ai or less g ai or less, 200 g ai or less, 190 g ai or less, 180 g ai or less, 170 g ai or less, 160 g ai or less, 150 g ai or less, 140 g ai or less, 130 g ai or less, 120 g ai or less, 110 g ai or less, 100 g ai or less, 95 g ai or less, 90 g ai or less, 85 g ai or less, 80 g ai or less, 75 g ai or less, 70 g ai or less, 65 g ai or less, 60 g ai or less, 55 g ai or less, 50 g ai or less, 45 g ai or less, 40 g ai or less, 35 g ai or less, 30 g ai or less, 25 g ai or less, 20 g ai or less, 15 g ai or less, 10 g ai or less ai or less, 9g ai or less, 8g ai or less, 7g ai or less, 6g ai or less, 5g ai or less, 4.5g ai or less, 4g ai or less, 3.5g ai or less, 3g ai or less, 2.5g ai or less, 2g ai or less, 1.5g ai or less, or 1g ai or less; or in an amount ranging from any of the above minimum values to any of the above maximum values, such as 1-4000g ai, 1-2240g ai, 1-150g ai, 1.5-3150g ai, 2-900g ai, 2.5-3200g ai, 3-1250g ai, 5-260g ai, 6-750g ai, 7-2100g ai, 10-2240g ai, 20-3600g ai, 40-3950g ai, 50-400g ai, 70-1250g ai, 100-1400g ai, or 250-1700g ai. Phenoxycarboxylic acid
[0270] In some aspects, the composition contains a compound according to Formula I, and (b) 2,4-D, 2,4-DB2, chlorformamide, 2,4-dichlorprop, 2-methyl-4-chloropropionic acid, MCPA, MCPB, or an agriculturally acceptable salt or ester thereof. 2,4-D
[0271] In some aspects, synthetic auxin herbicides may include 2,4-D or its agriculturally acceptable salt or ester. 2,4-D as shown below is a phenoxycarboxylic acid herbicide, which provides broad spectrum control of many annual, semi-annual and perennial broadleaf weeds and aquatic broadleaf weeds in cereals, corn, sorghum, grassland, established turf, grass seed crops, orchards (kernel and drupe), bilberry, asparagus, sugarcane, rice, woodlands and non-crop land (including areas adjacent to water). 2,4-D and methods for preparing 2,4-D are known in the art. Its herbicidal activity is described in, for example, The Pesticide Manual [pesticide manual], the seventeenth edition, 2016.
[0272] In some aspects, 2,4-D can be provided as an agriculturally acceptable salt or ester of 2,4-D. Exemplary agriculturally acceptable salts and esters of 2,4-D include, but are not limited to, 2,4-D-ammonium 2,4-D-butoxyethyl, 2,4-D-2-butoxypropyl, 2,4-D-3-butoxypropyl, 2,4-D-butyl, 2,4-D choline, 2,4-D-diethylammonium, 2,4-D-dimethylammonium (2,4-DDMA), 2,4-D-diethanolamine, 2,4-D-dodecylammonium, 2,4-D-ethyl, 2,4-D-2-ethylhexyl (2,4-D In some aspects, 2,4-D can be provided as 2,4-D-2-ethylhexyl (2,4-DEHE) as shown below.
[0273] In some aspects, the 2,4-D can be provided as 2,4-D DMA as shown below.
[0274] In some aspects, 2,4-D can be provided as 2,4-D choline as shown below.
[0275] In some aspects, 2,4-D can be provided as 2,4-D triethanolamine (2,4-D-trolamine) as shown below.
[0276] Exemplary uses of 2,4-D-choline include, but are not limited to, controlling annual and perennial broadleaf weeds, including, but not limited to, broadleaf weeds resistant to glyphosate. 2,4-D-choline can be used in crops that have been tolerant to 2,4-D, including, but not limited to, soybeans, corn, and cotton that are tolerant to 2,4-D. 2,4-D-choline is typically, but not necessarily, applied post-emergence. 2,4-D-choline can also be used for weed control in non-crop and perennial cropping systems.
[0277] 2,4-D may be applied to vegetation or areas adjacent to vegetation or to soil or water in an amount sufficient to induce a herbicidal action to prevent the emergence or growth of vegetation. In some aspects, 2,4-D is applied to vegetation or to areas adjacent to vegetation or to soil or water in an amount of 1 gram of active ingredient per hectare (g ai / ha) or more, such as 2 g ai / ha or more, 3 g ai / ha or more, 4 g ai / ha or more, 5 g ai / ha or more, 6 g ai / ha or more, 7 g ai / ha or more, 8 g ai / ha or more, 9 g ai / ha or more, 10 g ai / ha or more, 15 g ai / ha or more, 20 g ai / ha or more, 25 g ai / ha or more, 30 g ai / ha or more, 35 g ai / ha or more, 40 g ai / ha or more, 45 g ai / ha or more, 50 g ai / ha or more, 60 g ai / ha or more, 70 g ai / ha or more, 75 g ai / ha or more, 80 g ai / ha or more, 90 g ai / ha or more. g ai / ha or more, 100g ai / ha or more, 125g ai / ha or more, 150g ai / ha or more, 175g ai / ha or more, 200g ai / ha or more, 225g ai / ha or more, 250g ai / ha or more, 275g ai / ha or more, 300g ai / ha or more, 325g ai / ha or more, 350g ai / ha or more, 375g ai / ha or more, 400g ai / ha or more, 450g ai / ha or more, 500g ai / ha or more, 550g ai / ha or more, 600g ai / ha or more, 650g ai / ha or more, 700g ai / ha or more, 750g ai / ha or more, 800g ai / ha or more, 850g ai / ha or more, 900g ai / ha or more, 950g ai / ha or more g ai / ha or more, 1000g ai / ha or more, 1100g ai / ha or more, 1200g ai / ha or more, 1300g ai / ha or more, 1400g ai / ha or more, 1500g ai / ha or more, 1600g ai / ha or more, 1700g ai / ha or more, 1800g ai / ha or more, 1900g ai / ha or more, 2000g ai / ha or more, 2100g ai / ha or more, 2200g ai / ha or more, 2240g ai / ha or more, 2250g ai / ha or more, 2300g ai / ha or more, 2400g ai / ha or more, 2500g ai / ha or moreg ai / ha or more, 2600 g ai / ha or more, 2700 g ai / ha or more, 2800 g ai / ha or more, 2900 g ai / ha or more, 3000 g ai / ha or more, 3100 g ai / ha or more, 3200 g ai / ha or more, 3300 g ai / ha or more, 3400 g ai / ha or more, 3500 g ai / ha or more, 3600 g ai / ha or more, 3700 g ai / ha or more, 3750 g ai / ha or more, 3800 g ai / ha or more, 3850 g ai / ha or more, 3900 g ai / ha or more, or 3950 g ai / ha; in an amount of 4000 g ai / ha or less, such as 3950 g ai / ha or less, 3900 g ai / ha or more, g ai / ha or less, 3850 g ai / ha or less, 3800 g ai / ha or less, 3750 g ai / ha or less, 3700 g ai / ha or less, 3600 g ai / ha or less, 3500 g ai / ha or less, 3400 g ai / ha or less, 3300 g ai / ha or less, 3200 g ai / ha or less, 3100 g ai / ha or less, 3000 g ai / ha or less, 2900 g ai / ha or less, 2800 g ai / ha or less, 2700 g ai / ha or less, 2600 g ai / ha or less, 2500 g ai / ha or less, 2400 g ai / ha or less, 2300 g ai / ha or less, 2250 g ai / ha or less, 2240 g ai / ha or less. 1500g ai / ha or less, 1500g ai / ha or less, 1400g ai / ha or less, 1300g ai / ha or less, 1200g ai / ha or less, 1100g ai / ha or less, 1000g ai / ha or less, 950g ai / ha or less, 900g ai / ha or less, 850g ai / ha or less, 800g ai / ha or less, 750g ai / ha or less, 700g ai / ha or less, 650g ai / ha or less, 600g ai / ha or less. ai / ha or less, 550g ai / ha or less, 500g ai / ha or less, 450g ai / ha or less, 400g ai / ha or less, 375g ai / ha or less, 350gg ai / ha or less, 325 g ai / ha or less, 300 g ai / ha or less, 275 g ai / ha or less, 250 g ai / ha or less, 225 g ai / ha or less, 200 g ai / ha or less, 175 g ai / ha or less, 150 g ai / ha or less, 125 g ai / ha or less, 100 g ai / ha or less, 90 g ai / ha or less, 80 g ai / ha or less, 75 g ai / ha or less, 70 g ai / ha or less, 60 g ai / ha or less, 50 g ai / ha or less, 45 g ai / ha or less, 40 g ai / ha or less, 35 g ai / ha or less, 30 g ai / ha or less, 25 g ai / ha or less, 20 g ai / ha or less, 15 g ai / ha or less g ai / ha, 3-1500 g ai / ha, 4-2000 g ai / ha, 5-3000 g ai / ha, 6-4500 g ai / ha, 7-8000 g ai / ha, 8-1500 g ai / ha, 9-2000 g ai / ha, 10-2500 g ai / ha, 20-3000 g ai / ha, 30-3000 g ai / ha, 40-3000 g ai / ha, 50-3000 g ai / ha, 60-3000 g ai / ha, 70-3000 g ai / ha, 80-3000 g ai / ha, 80-3000 g ai / ha, 80-3000 g ai / ha, 90-3000 g ai / ha, 100-2500 g ai / ha, 100-2500 g ai / ha, 100-2500 g ai / ha, 100-2500 g ai / ha, 100 ai / ha, 50-400g ai / ha, 70-2400g ai / ha, 100-950g ai / ha, or 250-1700g ai / ha. 2,4-DB
[0278] In some aspects, the synthetic auxin herbicide may include 2,4-DB, which is a phenoxycarboxylic acid herbicide that provides post-emergence control of many annual and perennial broadleaf weeds in alfalfa, clover, cereals, grasslands, forages, legumes, soybeans, and peanuts. 2,4-DB and methods for preparing 2,4-DB are known in the art. Its herbicidal activity is described in The Pesticide Manual, Seventeenth Edition, 2016.
[0279] In some aspects, 2,4-DB can be provided as an agriculturally acceptable salt or ester of 2,4-DB. Exemplary agriculturally acceptable salts and esters of 2,4-DB include, but are not limited to, 2,4-DB-butyl, 2,4-DB-dimethylammonium (2,4-DB DMA), 2,4-DB-isooctyl, 2,4-DB-potassium, and 2,4-DB-sodium.
[0280] 2,4-DB may be applied to vegetation or areas adjacent to vegetation or to soil or water in an amount sufficient to induce a herbicidal effect to prevent the emergence or growth of vegetation. In some aspects, 2,4-DB is applied to vegetation or to an area adjacent to vegetation or to soil or water in an amount of 1 g ai / ha or more, such as 2 g ai / ha or more, 3 g ai / ha or more, 4 g ai / ha or more, 5 g ai / ha or more, 6 g ai / ha or more, 7 g ai / ha or more, 8 g ai / ha or more, 9 g ai / ha or more, 10 g ai / ha or more, 15 g ai / ha or more, 20 g ai / ha or more, 25 g ai / ha or more, 30 g ai / ha or more, 35 g ai / ha or more, 40 g ai / ha or more, 45 g ai / ha or more, 50 g ai / ha or more, 60 g ai / ha or more, 70 g ai / ha or more, 75 g ai / ha or more, 80 g ai / ha or more, 90 g ai / ha or more, 100 g ai / ha or more. g ai / ha or more, 125g ai / ha or more, 150g ai / ha or more, 175g ai / ha or more, 200g ai / ha or more, 225g ai / ha or more, 250g ai / ha or more, 275g ai / ha or more, 300g ai / ha or more, 325g ai / ha or more, 350g ai / ha or more, 375g ai / ha or more, 400g ai / ha or more, 450g ai / ha or more, 500g ai / ha or more, 550g ai / ha or more, 600g ai / ha or more, 650g ai / ha or more, 700g ai / ha or more, 750g ai / ha or more, 800g ai / ha or more, 850g ai / ha or more, 900g ai / ha or more, 950g ai / ha or more g ai / ha or more, 1000 g ai / ha or more, 1100 g ai / ha or more, 1200 g ai / ha or more, 1300 g ai / ha or more, 1400 g ai / ha or more, 1500 g ai / ha or more, 1600 g ai / ha or more, 1700 g ai / ha or more, 1800 g ai / ha or more, 1900 g ai / ha or more, 2000 g ai / ha or more, 2100 g ai / ha or more, 2200 g ai / ha or more, 2240 g ai / ha or more, 2250 g ai / ha or more, 2300 g ai / ha or more, 2400 g ai / ha or more, 2500 g ai / ha or moreg ai / ha or more, 2600 g ai / ha or more, 2700 g ai / ha or more, 2800 g ai / ha or more, 2900 g ai / ha or more, 3000 g ai / ha or more, 3100 g ai / ha or more, 3200 g ai / ha or more, 3300 g ai / ha or more, 3400 g ai / ha or more, 3500 g ai / ha or more, 3600 g ai / ha or more, 3700 g ai / ha or more, 3750 g ai / ha or more, 3800 g ai / ha or more, 3850 g ai / ha or more, 3900 g ai / ha or more, or 3950 g ai / ha; in an amount of 4000 g ai / ha or less, such as 3950 g ai / ha or less, 3900 g ai / ha or less, 3850 g ai / ha or more, g ai / ha or less, 3800g ai / ha or less, 3750g ai / ha or less, 3700g ai / ha or less, 3600g ai / ha or less, 3500g ai / ha or less, 3400g ai / ha or less, 3300g ai / ha or less, 3200g ai / ha or less, 3100g ai / ha or less, 3000g ai / ha or less, 2900g ai / ha or less, 2800g ai / ha or less, 2700g ai / ha or less, 2600g ai / ha or less, 2500g ai / ha or less, 2400g ai / ha or less, 2300g ai / ha or less, 2250g ai / ha or less, 2240g ai / ha or less, 2200g ai / ha or less. g ai / ha or less, 2100 g ai / ha or less, 2000 g ai / ha or less, 1900 g ai / ha or less, 1800 g ai / ha or less, 1700 g ai / ha or less, 1600 g ai / ha or less, 1500 g ai / ha or less, 1400 g ai / ha or less, 1300 g ai / ha or less, 1200 g ai / ha or less, 1100 g ai / ha or less, 1000 g ai / ha or less, 950 g ai / ha or less, 900 g ai / ha or less, 850 g ai / ha or less, 800 g ai / ha or less, 750 g ai / ha or less, 700 g ai / ha or less, 650 g ai / ha or less, 600 g ai / ha or less, 550 g ai / ha or less, ai / ha or less, 500g ai / ha or less, 450g ai / ha or less, 400g ai / ha or less, 375g ai / ha or less, 350gg ai / ha or less, 325 g ai / ha or less, 300 g ai / ha or less, 275 g ai / ha or less, 250 g ai / ha or less, 225 g ai / ha or less, 200 g ai / ha or less, 175 g ai / ha or less, 150 g ai / ha or less, 125 g ai / ha or less, 100 g ai / ha or less, 90 g ai / ha or less, 80 g ai / ha or less, 75 g ai / ha or less, 70 g ai / ha or less, 60 g ai / ha or less, 50 g ai / ha or less, 45 g ai / ha or less, 40 g ai / ha or less, 35 g ai / ha or less, 30 g ai / ha or less, 25 g ai / ha or less, 20 g ai / ha or less, 15 g ai / ha or less g ai / ha, 10g ai / ha or less, 9g ai / ha or less, 8g ai / ha or less, 7g ai / ha or less, 6g ai / ha or less, 5g ai / ha or less, 4g ai / ha or less, 3g ai / ha or less, or 2g ai / ha or less; or in an amount ranging from any of the above minimum values to any of the above maximum values, such as 1-4000 g ai / ha, 1-150 g ai / ha, 2-3100 g ai / ha, 2-900 g ai / ha, 3-2600 g ai / ha, 3-1200 g ai / ha, 5-275 g ai / ha, 6-750 g ai / ha, 7-2100 g ai / ha, 10-2240 g ai / ha, 20-3300 g ai / ha, 40-3950 g ai / ha, 50-400g ai / ha, 70-2400g ai / ha, 100-950g ai / ha, or 250-1700g ai / ha. Chloroformamide
[0281] In some aspects, the synthetic auxin herbicide may include chlorambucil or an agriculturally acceptable salt or ester thereof. Chlorambucil, as shown below, is a phenoxycarboxylic acid herbicide that provides pre-emergence to early post-emergence control of broadleaf weeds and sedge weeds in rice. Chlorambucil and methods for preparing chlorambucil are known in the art. Its herbicidal activity is described, for example, in The Pesticide Manual, Seventeenth Edition, 2016. 2,4-Dichloropropionic acid
[0282] In some aspects, the synthetic auxin herbicide may include 2,4-dichloropropionic acid or an agriculturally acceptable salt or ester thereof. 2,4-dichloropropionic acid, as shown below, is a phenoxycarboxylic acid herbicide that provides broad-spectrum control of annual and perennial broadleaf weeds in cereals and grasslands; shrub control on non-crop lands; control of broadleaf aquatic weeds; and maintenance of road embankments and roadside grasslands. 2,4-dichloropropionic acid and methods for preparing 2,4-dichloropropionic acid are known in the art. Its herbicidal activity is described, for example, in The Pesticide Manual, Seventeenth Edition, 2016.
[0283] In some aspects, 2,4-dichloropropionic acid can be provided as an agriculturally acceptable salt or ester of 2,4-dichloropropionic acid. Exemplary agriculturally acceptable salts and esters of 2,4-dichloropropionic acid include but are not limited to 2,4-dichloropropionic acid-butoxyethyl, 2,4-dichloropropionic acid-dimethylammonium, 2,4-dichloropropionic acid-ethylammonium, 2,4-dichloropropionic acid-2-ethylhexyl, 2,4-dichloropropionic acid-isooctyl, 2,4-dichloropropionic acid-methyl, 2,4-dichloropropionic acid-potassium, 2,4-dichloropropionic acid-sodium, refined 2,4-dichloropropionic acid, refined 2,4-dichloropropionic acid-dimethylammonium, refined 2,4-dichloropropionic acid-2-ethylhexyl, refined 2,4-dichloropropionic acid-potassium and refined 2,4-dichloropropionic acid-sodium. In some aspects, 2,4-dichloropropionic acid can be provided as a stereoisomer refined 2,4-dichloropropionic acid as shown below.
[0284] Dichlorvos may be applied to vegetation or areas adjacent to vegetation or to soil or water in an amount sufficient to induce a herbicidal effect to prevent the emergence or growth of vegetation. In some aspects, 2,4-dichloropropane is applied to vegetation or an area adjacent to vegetation or to soil or water in an amount of 1 g ai / ha or more, such as 2 g ai / ha or more, 3 g ai / ha or more, 4 g ai / ha or more, 5 g ai / ha or more, 6 g ai / ha or more, 7 g ai / ha or more, 8 g ai / ha or more, 9 g ai / ha or more, 10 g ai / ha or more, 15 g ai / ha or more, 20 g ai / ha or more, 25 g ai / ha or more, 30 g ai / ha or more, 35 g ai / ha or more, 40 g ai / ha or more, 45 g ai / ha or more, 50 g ai / ha or more, 60 g ai / ha or more, 70 g ai / ha or more, 75 g ai / ha or more, 80 g ai / ha or more, 90 g ai / ha or more, 100 g ai / ha or more. g ai / ha or more, 125g ai / ha or more, 150g ai / ha or more, 175g ai / ha or more, 200g ai / ha or more, 225g ai / ha or more, 250g ai / ha or more, 275g ai / ha or more, 300g ai / ha or more, 325g ai / ha or more, 350g ai / ha or more, 375g ai / ha or more, 400g ai / ha or more, 450g ai / ha or more, 500g ai / ha or more, 550g ai / ha or more, 600g ai / ha or more, 650g ai / ha or more, 700g ai / ha or more, 750g ai / ha or more, 800g ai / ha or more, 850g ai / ha or more, 900g ai / ha or more, 950g ai / ha or more g ai / ha or more, 1000 g ai / ha or more, 1100 g ai / ha or more, 1200 g ai / ha or more, 1300 g ai / ha or more, 1400 g ai / ha or more, 1500 g ai / ha or more, 1600 g ai / ha or more, 1700 g ai / ha or more, 1800 g ai / ha or more, 1900 g ai / ha or more, 2000 g ai / ha or more, 2100 g ai / ha or more, 2200 g ai / ha or more, 2240 g ai / ha or more, 2250 g ai / ha or more, 2300 g ai / ha or more, 2400 g ai / ha or more, 2500 g ai / ha or moreg ai / ha or more, 2600 g ai / ha or more, 2700 g ai / ha or more, 2800 g ai / ha or more, 2900 g ai / ha or more, 3000 g ai / ha or more, 3100 g ai / ha or more, 3200 g ai / ha or more, 3300 g ai / ha or more, 3400 g ai / ha or more, 3500 g ai / ha or more, 3600 g ai / ha or more, 3700 g ai / ha or more, 3750 g ai / ha or more, 3800 g ai / ha or more, 3850 g ai / ha or more, 3900 g ai / ha or more, or 3950 g ai / ha; in an amount of 4000 g ai / ha or less, such as 3950 g ai / ha or less, 3900 g ai / ha or less, 3850 g ai / ha or more, g ai / ha or less, 3800g ai / ha or less, 3750g ai / ha or less, 3700g ai / ha or less, 3600g ai / ha or less, 3500g ai / ha or less, 3400g ai / ha or less, 3300g ai / ha or less, 3200g ai / ha or less, 3100g ai / ha or less, 3000g ai / ha or less, 2900g ai / ha or less, 2800g ai / ha or less, 2700gai / ha or less, 2600g ai / ha or less, 2500g ai / ha or less, 2400g ai / ha or less, 2300g ai / ha or less, 2250g ai / ha or less, 2240g ai / ha or less, 2200g ai / ha or less g ai / ha or less, 2100 g ai / ha or less, 2000 g ai / ha or less, 1900 g ai / ha or less, 1800 g ai / ha or less, 1700 g ai / ha or less, 1600 g ai / ha or less, 1500 g ai / ha or less, 1400 g ai / ha or less, 1300 g ai / ha or less, 1200 g ai / ha or less, 1100 g ai / ha or less, 1000 g ai / ha or less, 950 g ai / ha or less, 900 g ai / ha or less, 850 g ai / ha or less, 800 g ai / ha or less, 750 g ai / ha or less, 700 g ai / ha or less, 650 g ai / ha or less, 600 g ai / ha or less, 550 g ai / ha or less, ai / ha or less, 500g ai / ha or less, 450g ai / ha or less, 400g ai / ha or less, 375g ai / ha or less, 350gg ai / ha or less, 325 g ai / ha or less, 300 g ai / ha or less, 275 g ai / ha or less, 250 g ai / ha or less, 225 g ai / ha or less, 200 g ai / ha or less, 175 g ai / ha or less, 150 g ai / ha or less, 125 g ai / ha or less, 100 g ai / ha or less, 90 g ai / ha or less, 80 g ai / ha or less, 75 g ai / ha or less, 70 g ai / ha or less, 60 g ai / ha or less, 50 g ai / ha or less, 45 g ai / ha or less, 40 g ai / ha or less, 35 g ai / ha or less, 30 g ai / ha or less, 25 g ai / ha or less, 20 g ai / ha or less, 15 g ai / ha or less, g ai / ha, 10g ai / ha or less, 9g ai / ha or less, 8g ai / ha or less, 7g ai / ha or less, 6g ai / ha or less, 5g ai / ha or less, 4g ai / ha or less, 3g ai / ha or less, or 2g ai / ha or less; or in an amount ranging from any of the above minimum values to any of the above maximum values, such as 1-4000 g ai / ha, 1-150 g ai / ha, 2-3100 g ai / ha, 2-900 g ai / ha, 3-2600 g ai / ha, 3-1200 g ai / ha, 5-275 g ai / ha, 6-750 g ai / ha, 7-2100 g ai / ha, 10-2240 g ai / ha, 20-3300 g ai / ha, 40-3950 g ai / ha, 50-400g ai / ha, 70-2400g ai / ha, 100-950g ai / ha, or 250-1700g ai / ha. 2-Methyl-4-chloropropionic acid
[0285] In some aspects, synthetic auxin herbicides may include 2-methyl-4-chloropropionic acid or its agriculturally acceptable salt or ester. 2-methyl-4-chloropropionic acid as shown below is a phenoxycarboxylic acid herbicide that provides a broad spectrum control of broadleaf weeds in wheat, barley, oats, forage seed crops, grasslands, and under fruit trees and lianas. 2-methyl-4-chloropropionic acid also provides control of sorrel (Rumex spp.) in grasslands and pastures. 2-methyl-4-chloropropionic acid and methods for preparing 2-methyl-4-chloropropionic acid are known in the art. Its herbicidal activity is described in The Pesticide Manual [pesticide manual], the seventeenth edition, 2016.
[0286] In some aspects, 2-methyl-4-chloropropionic acid can be provided as an agriculturally acceptable salt or ester of 2-methyl-4-chloropropionic acid. Exemplary agriculturally acceptable salts and esters of 2-methyl-4-chloropropionic acid include, but are not limited to, 2-methyl-4-chloropropionic acid-butoxyethyl, 2-methyl-4-chloropropionic acid-potassium, 2-methyl-4-chloropropionic acid-sodium, 2-methyl-4-chloropropionic acid-dimethylammonium, 2-methyl-4-chloropropionic acid-diethanolamine, 2-methyl-4-chloropropionic acid-ethadyl, 2-methyl-4-chloropropionic acid-2-ethylhexyl, 2-methyl-4-chloropropionic acid-isooctyl, 2-methyl-4-chloropropionic acid-methyl, 2-methyl-4-chloropropionic acid-triethanolamine, 2-methyl-4-chloropropionic acid, 2-methyl-4-chloropropionic acid-butoxyethyl, 2-methyl-4-chloropropionic acid-dimethylammonium, 2-methyl-4-chloropropionic acid-ethylhexyl, and 2-methyl-4-chloropropionic acid-potassium. In some aspects, 2-methyl-4-chloropropionic acid can be provided as the stereoisomer pure 2-methyl-4-chloropropionic acid as shown below.
[0287] 2-Methyl-4-chloropropionic acid may be applied to vegetation or areas adjacent to vegetation or to soil or water in an amount sufficient to induce a herbicidal effect to prevent the emergence or growth of vegetation. In some aspects, 2-methyl-4-chloropropionic acid is applied to vegetation or an area adjacent to vegetation or to soil or water in an amount of 1 g ai / ha or more, such as 2 g ai / ha or more, 3 g ai / ha or more, 4 g ai / ha or more, 5 g ai / ha or more, 6 g ai / ha or more, 7 g ai / ha or more, 8 g ai / ha or more, 9 g ai / ha or more, 10 g ai / ha or more, 15 g ai / ha or more, 20 g ai / ha or more, 25 g ai / ha or more, 30 g ai / ha or more, 35 g ai / ha or more, 40 g ai / ha or more, 45 g ai / ha or more, 50 g ai / ha or more, 60 g ai / ha or more, 70 g ai / ha or more, 75 g ai / ha or more, 80 g ai / ha or more, 90 g ai / ha or more, 100 g ai / ha or more. g ai / ha or more, 125 g ai / ha or more, 150 g ai / ha or more, 175 g ai / ha or more, 200 g ai / ha or more, 225 g ai / ha or more, 250 g ai / ha or more, 275 g ai / ha or more, 300 g ai / ha or more, 325 g ai / ha or more, 350 g ai / ha or more, 375 g ai / ha or more, 400 g ai / ha or more, 450 g ai / ha or more, 500 g ai / ha or more, 550 g ai / ha or more, 600 g ai / ha or more, 650 g ai / ha or more, 700 g ai / ha or more, 750 g ai / ha or more, 800 g ai / ha or more, 850 g ai / ha or more, 900 g ai / ha or more, 950 g ai / ha or more, 1000 g ai / ha or more g ai / ha or more, 1100g ai / ha or more, 1200g ai / ha or more, 1300g ai / ha or more, 1400g ai / ha or more, 1500g ai / ha or more, 1600g ai / ha or more, 1700g ai / ha or more, 1800g ai / ha or more, 1900g ai / ha or more, 2000g ai / ha or more, 2100g ai / ha or more, 2200g ai / ha or more, 2240g ai / ha or more, 2250g ai / ha or more, 2300g ai / ha or more, 2400g ai / ha or more, 2500g ai / ha or moreg ai / ha or more, 2600 g ai / ha or more, 2700 g ai / ha or more, 2800 g ai / ha or more, 2900 g ai / ha or more, 3000 g ai / ha or more, 3100 g ai / ha or more, 3200 g ai / ha or more, 3300 g ai / ha or more, 3400 g ai / ha or more, 3500 g ai / ha or more, 3600 g ai / ha or more, 3700 g ai / ha or more, 3750 g ai / ha or more, 3800 g ai / ha or more, 3850 g ai / ha or more, 3900 g ai / ha or more, or 3950 g ai / ha; in an amount of 4000 g ai / ha or less, such as 3950 g ai / ha or less, 3900 g ai / ha or more, g ai / ha or less, 3850 g ai / ha or less, 3800 g ai / ha or less, 3750 g ai / ha or less, 3700 g ai / ha or less, 3600 g ai / ha or less, 3500 g ai / ha or less, 3400 g ai / ha or less, 3300 g ai / ha or less, 3200 g ai / ha or less, 3100 g ai / ha or less, 3000 g ai / ha or less, 2900 g ai / ha or less, 2800 g ai / ha or less, 2700 g ai / ha or less, 2600 g ai / ha or less, 2500 g ai / ha or less, 2400 g ai / ha or less, 2300 g ai / ha or less, 2250 g ai / ha or less, 2240 g ai / ha or less. 1500g ai / ha or less, 1500g ai / ha or less, 1400g ai / ha or less, 1300g ai / ha or less, 1200g ai / ha or less, 1100g ai / ha or less, 1000g ai / ha or less, 950g ai / ha or less, 900g ai / ha or less, 850g ai / ha or less, 800g ai / ha or less, 750g ai / ha or less, 700g ai / ha or less, 650g ai / ha or less, 600g ai / ha or less. ai / ha or less, 550g ai / ha or less, 500g ai / ha or less, 450g ai / ha or less, 400g ai / ha or less, 375g ai / ha or less, 350gg ai / ha or less, 325 g ai / ha or less, 300 g ai / ha or less, 275 g ai / ha or less, 250 g ai / ha or less, 225 g ai / ha or less, 200 g ai / ha or less, 175 g ai / ha or less, 150 g ai / ha or less, 125 g ai / ha or less, 100 g ai / ha or less, 90 g ai / ha or less, 80 g ai / ha or less, 75 g ai / ha or less, 70 g ai / ha or less, 60 g ai / ha or less, 50 g ai / ha or less, 45 g ai / ha or less, 40 g ai / ha or less, 35 g ai / ha or less, 30 g ai / ha or less, 25 g ai / ha or less, 20 g ai / ha or less, 15 g ai / ha or less g ai / ha, 3-1500 g ai / ha, 4-2000 g ai / ha, 5-3000 g ai / ha, 6-4500 g ai / ha, 7-8000 g ai / ha, 8-1500 g ai / ha, 9-2000 g ai / ha, 10-2500 g ai / ha, 20-3000 g ai / ha, 30-3000 g ai / ha, 40-3000 g ai / ha, 50-3000 g ai / ha, 60-3000 g ai / ha, 70-3000 g ai / ha, 80-3000 g ai / ha, 80-3000 g ai / ha, 80-3000 g ai / ha, 90-3000 g ai / ha, 100-2500 g ai / ha, 100-2500 g ai / ha, 100-2500 g ai / ha, 100-2500 g ai / ha, 100 ai / ha, 50-400g ai / ha, 70-2400g ai / ha, 100-950g ai / ha, or 250-1700g ai / ha. MCPA
[0288] In some aspects, synthetic auxin herbicides may include MCPA or its agriculturally acceptable salt or ester. MCPA as shown below is a phenoxycarboxylic acid herbicide that provides broad-spectrum control of many annual, semi-annual and perennial broadleaf weeds, woody weeds and aquatic broadleaf weeds in cereals, forage seed crops, flax, rice, lianas, peas, potatoes, asparagus, grasslands, turf, fruit trees, forest floors, and roadside meadows and embankments. MCPA and methods for preparing MCPA are known in the art. Its herbicidal activity is described in, for example, The Pesticide Manual, the 17th edition, 2016.
[0289] In some aspects, MCPA can be provided as an agriculturally acceptable salt or ester of MCPA. Exemplary agriculturally acceptable salts of MCPA include, but are not limited to, MCPA-butoxyethyl, MCPA-butyl, MCPA-dimethylammonium (MCPA-DMA), MCPA-diethanolamine, MCPA-ethyl, MCPA-2-ethylhexyl (MCPA EHE), MCPA-isobutyl, MCPA-isooctyl, MCPA-isopropyl, MCPA-methyl, MCPA-ethanolamine, MCPA-potassium, MCPA-sodium, MCPA-triethanolamine. In some aspects, MCPA can be provided as MCPA-2-ethylhexyl (MCPA EHE) as shown below.
[0290] In some aspects, MCPA can be provided as MCPA-dimethylammonium (MCPA-DMA) as shown below.
[0291] MCPA may be applied to vegetation or areas adjacent to vegetation or to soil or water in an amount sufficient to induce a herbicidal effect to prevent the emergence or growth of vegetation. In some aspects, MCPA is applied to vegetation or an area adjacent to vegetation or to soil or water in an amount of 1 g ai / ha or more, such as 2 g ai / ha or more, 3 g ai / ha or more, 4 g ai / ha or more, 5 g ai / ha or more, 6 g ai / ha or more, 7 g ai / ha or more, 8 g ai / ha or more, 9 g ai / ha or more, 10 g ai / ha or more, 15 g ai / ha or more, 20 g ai / ha or more, 25 g ai / ha or more, 30 g ai / ha or more, 35 g ai / ha or more, 40 g ai / ha or more, 45 g ai / ha or more, 50 g ai / ha or more, 60 g ai / ha or more, 70 g ai / ha or more, 75 g ai / ha or more, 80 g ai / ha or more, 90 g ai / ha or more, 100 g ai / ha or more. g ai / ha or more, 125g ai / ha or more, 150g ai / ha or more, 175g ai / ha or more, 200g ai / ha or more, 225g ai / ha or more, 250g ai / ha or more, 275g ai / ha or more, 300g ai / ha or more, 325g ai / ha or more, 350g ai / ha or more, 375g ai / ha or more, 400g ai / ha or more, 450g ai / ha or more, 500g ai / ha or more, 550g ai / ha or more, 600g ai / ha or more, 650g ai / ha or more, 700g ai / ha or more, 750g ai / ha or more, 800g ai / ha or more, 850g ai / ha or more, 900g ai / ha or more, 950g ai / ha or more g ai / ha or more, 1000g ai / ha or more, 1100g ai / ha or more, 1200g ai / ha or more, 1300g ai / ha or more, 1400g ai / ha or more, 1500g ai / ha or more, 1600g ai / ha or more, 1700g ai / ha or more, 1800g ai / ha or more, 1900g ai / ha or more, 2000g ai / ha or more, 2100g ai / ha or more, 2200g ai / ha or more, 2240g ai / ha or more, 2250g ai / ha or more, 2300g ai / ha or more, 2400g ai / ha or more, 2500g ai / ha or more, 2600g ai / ha or moreg ai / ha or more, 2700 g ai / ha or more, 2800 g ai / ha or more, 2900 g ai / ha or more, 3000 g ai / ha or more, 3100 g ai / ha or more, 3200 g ai / ha or more, 3300 g ai / ha or more, 3400 g ai / ha or more, 3500 g ai / ha or more, 3600 g ai / ha or more, 3700 g ai / ha or more, 3750 g ai / ha or more, 3800 g ai / ha or more, 3850 g ai / ha or more, 3900 g ai / ha or more, or 3950 g ai / ha; in an amount of 4000 g ai / ha or less, such as 3950 g ai / ha or less, 3900 g ai / ha or less, 3850 g ai / ha or less, 3800 g ai / ha or more, 0g ai / ha or less, 3750g ai / ha or less, 3700g ai / ha or less, 3600g ai / ha or less, 3500g ai / ha or less, 3400g ai / ha or less, 3300g ai / ha or less, 3200g ai / ha or less, 3100g ai / ha or less, 3000g ai / ha or less, 2900g ai / ha or less, 2800g ai / ha or less, 2700g ai / ha or less, 2600g ai / ha or less, 2500g ai / ha or less, 2400g ai / ha or less, 2300g ai / ha or less, 2250g ai / ha or less, 2240g ai / ha or less, 2200g ai / ha or less, 2100g ai / ha or less g ai / ha or less, 2000 g ai / ha or less, 1900 g ai / ha or less, 1800 g ai / ha or less, 1700 g ai / ha or less, 1600 g ai / ha or less, 1500 g ai / ha or less, 1400 g ai / ha or less, 1300 g ai / ha or less, 1200 g ai / ha or less, 1100 g ai / ha or less, 1000 g ai / ha or less, 950 g ai / ha or less, 900 g ai / ha or less, 850 g ai / ha or less, 800 g ai / ha or less, 750 g ai / ha or less, 700 g ai / ha or less, 650 g ai / ha or less, 600 g ai / ha or less, 550 g ai / ha or less, 500 g ai / ha or less ai / ha or less, 450g ai / ha or less, 400g ai / ha or less, 375g ai / ha or less, 350g ai / ha or less, 325gg ai / ha or less, 300 g ai / ha or less, 275 g ai / ha or less, 250 g ai / ha or less, 225 g ai / ha or less, 200 g ai / ha or less, 175 g ai / ha or less, 150 g ai / ha or less, 125 g ai / ha or less, 100 g ai / ha or less, 90 g ai / ha or less, 80 g ai / ha or less, 75 g ai / ha or less, 70 g ai / ha or less, 60 g ai / ha or less, 50 g ai / ha or less, 45 g ai / ha or less, 40 g ai / ha or less, 35 g ai / ha or less, 30 g ai / ha or less, 25 g ai / ha or less, 20 g ai / ha or less, 15 g ai / ha or less, 10 g ai / ha or less, 9 g ai / ha or less, ai / ha or less, 8g ai / ha or less, 7g ai / ha or less, 6g ai / ha or less, 5g ai / ha or less, 4g ai / ha or less, 3g ai / ha or less, or 2g ai / ha or less; or in an amount ranging from any of the above minimum values to any of the above maximum values, such as 1-4000g ai / ha, 1-150g ai / ha, 2-3100g ai / ha, 2-900g ai / ha, 3-2600g ai / ha, 3-1200g ai / ha, 5-275g ai / ha, 6-750g ai / ha, 7-2100g ai / ha, 10-2240g ai / ha, 20-3300g ai / ha, 40-3950g ai / ha, 50-400g ai / ha, 70-2400g ai / ha, 100-950g ai / ha, or 250-1700gai / ha. MCPB
[0292] In some aspects, the synthetic auxin herbicide may include MCPB or an agriculturally acceptable salt or ester thereof. MCPB, as shown below, is a phenoxycarboxylic acid herbicide that provides broad-spectrum control of many broadleaf weeds, woody weeds, and aquatic broadleaf weeds in rice, cereals, clover, sainfoin, peas, peanuts, grasslands, turf, and woodlands. MCPB and methods for preparing MCPB are known in the art. Its herbicidal activity is described, for example, in The Pesticide Manual, Seventeenth Edition, 2016.
[0293] In some aspects, MCPB can be provided as an agriculturally acceptable salt or ester of MCPB. Exemplary agriculturally acceptable salts of MCPB include, but are not limited to, MCPB-ethyl, MCPB-potassium, and MCPB-sodium.
[0294] MCPB may be applied to vegetation or areas adjacent to vegetation or to soil or water in an amount sufficient to induce a herbicidal effect to prevent the emergence or growth of vegetation. In some aspects, MCPB is applied to vegetation or to an area adjacent to vegetation, or to soil or water in an amount of 1 g ai / ha or more, such as 2 g ai / ha or more, 3 g ai / ha or more, 4 g ai / ha or more, 5 g ai / ha or more, 6 g ai / ha or more, 7 g ai / ha or more, 8 g ai / ha or more, 9 g ai / ha or more, 10 g ai / ha or more, 15 g ai / ha or more, 20 g ai / ha or more, 25 g ai / ha or more, 30 g ai / ha or more, 35 g ai / ha or more, 40 g ai / ha or more, 45 g ai / ha or more, 50 g ai / ha or more, 60 g ai / ha or more, 70 g ai / ha or more, 75 g ai / ha or more, 80 g ai / ha or more, 90 g ai / ha or more, 100 g ai / ha or more. g ai / ha or more, 125g ai / ha or more, 150g ai / ha or more, 175g ai / ha or more, 200g ai / ha or more, 225g ai / ha or more, 250g ai / ha or more, 275g ai / ha or more, 300g ai / ha or more, 325g ai / ha or more, 350g ai / ha or more, 375g ai / ha or more, 400g ai / ha or more, 450g ai / ha or more, 500g ai / ha or more, 550g ai / ha or more, 600g ai / ha or more, 650g ai / ha or more, 700g ai / ha or more, 750g ai / ha or more, 800g ai / ha or more, 850g ai / ha or more, 900g ai / ha or more, 950g ai / ha or more g ai / ha or more, 1000g ai / ha or more, 1100g ai / ha or more, 1200g ai / ha or more, 1300g ai / ha or more, 1400g ai / ha or more, 1500g ai / ha or more, 1600g ai / ha or more, 1700g ai / ha or more, 1800g ai / ha or more, 1900g ai / ha or more, 2000g ai / ha or more, 2100g ai / ha or more, 2200g ai / ha or more, 2240g ai / ha or more, 2250g ai / ha or more, 2300g ai / ha or more, 2400g ai / ha or more, 2500g ai / ha or more, 2600g ai / ha or moreg ai / ha or more, 2700 g ai / ha or more, 2800 g ai / ha or more, 2900 g ai / ha or more, 3000 g ai / ha or more, 3100 g ai / ha or more, 3200 g ai / ha or more, 3300 g ai / ha or more, 3400 g ai / ha or more, 3500 g ai / ha or more, 3600 g ai / ha or more, 3700 g ai / ha or more, 3750 g ai / ha or more, 3800 g ai / ha or more, 3850 g ai / ha or more, 3900 g ai / ha or more, or 3950 g ai / ha; in an amount of 4000 g ai / ha or less, such as 3950 g ai / ha or less, 3900 g ai / ha or less, 3850 g ai / ha or less, 3800 g ai / ha or more, 0g ai / ha or less, 3750g ai / ha or less, 3700g ai / ha or less, 3600g ai / ha or less, 3500g ai / ha or less, 3400g ai / ha or less, 3300g ai / ha or less, 3200g ai / ha or less, 3100g ai / ha or less, 3000g ai / ha or less, 2900g ai / ha or less, 2800g ai / ha or less, 2700g ai / ha or less, 2600g ai / ha or less, 2500g ai / ha or less, 2400g ai / ha or less, 2300g ai / ha or less, 2250g ai / ha or less, 2240g ai / ha or less, 2200g ai / ha or less, 2100g ai / ha or less g ai / ha or less, 2000 g ai / ha or less, 1900 g ai / ha or less, 1800 g ai / ha or less, 1700 g ai / ha or less, 1600 g ai / ha or less, 1500 g ai / ha or less, 1400 g ai / ha or less, 1300 g ai / ha or less, 1200 g ai / ha or less, 1100 g ai / ha or less, 1000 g ai / ha or less, 950 g ai / ha or less, 900 g ai / ha or less, 850 g ai / ha or less, 800 g ai / ha or less, 750 g ai / ha or less, 700 g ai / ha or less, 650 g ai / ha or less, 600 g ai / ha or less, 550 g ai / ha or less, 500 g ai / ha or less ai / ha or less, 450g ai / ha or less, 400g ai / ha or less, 375g ai / ha or less, 350g ai / ha or less, 325gg ai / ha or less, 300 g ai / ha or less, 275 g ai / ha or less, 250 g ai / ha or less, 225 g ai / ha or less, 200 g ai / ha or less, 175 g ai / ha or less, 150 g ai / ha or less, 125 g ai / ha or less, 100 g ai / ha or less, 90 g ai / ha or less, 80 g ai / ha or less, 75 g ai / ha or less, 70 g ai / ha or less, 60 g ai / ha or less, 50 g ai / ha or less, 45 g ai / ha or less, 40 g ai / ha or less, 35 g ai / ha or less, 30 g ai / ha or less, 25 g ai / ha or less, 20 g ai / ha or less, 15 g ai / ha or less, 10 g ai / ha or less, 9 g ai / ha or less, ai / ha or less, 8g ai / ha or less, 7g ai / ha or less, 6g ai / ha or less, 5g ai / ha or less, 4g ai / ha or less, 3g ai / ha or less, or 2g ai / ha or less; or in an amount ranging from any of the above minimum values to any of the above maximum values, such as 1-4000g ai / ha, 1-150g ai / ha, 2-3100g ai / ha, 2-900g ai / ha, 3-2600g ai / ha, 3-1200g ai / ha, 5-275g ai / ha, 6-750g ai / ha, 7-2100g ai / ha, 10-2240g ai / ha, 20-3300g ai / ha, 40-3950g ai / ha, 50-400g ai / ha, 70-2400g ai / ha, 100-950g ai / ha, or 250-1700gai / ha. benzoic acid
[0295] In some aspects, the composition contains a compound according to Formula I, and (b) fenpropimorph, dicamba, TBA, or an agriculturally acceptable salt or ester thereof. Metformin
[0296] In some aspects, synthetic auxin herbicides may include fenflurazole or an agriculturally acceptable salt or ester thereof.fenflurazole, as shown below, is a benzoic acid herbicide that provides pre-planting and pre-emergence control of grass and broadleaf weeds in asparagus, navy beans, peanuts, corn, sweet potatoes, pumpkins, soybeans, zucchini, sunflowers, and certain ornamental plants.fenflurazole and methods for preparing fenflurazole are known in the art. Its herbicidal activity is described, for example, in The Pesticide Manual, Seventeenth Edition, 2016. Dicamba
[0297] In some aspects, synthetic auxin herbicides may include dicamba or its agriculturally acceptable salt or ester. As shown below, dicamba is a benzoic acid herbicide that provides broad-spectrum control of annual and perennial broadleaf weeds and shrub species in cereals, corn, sorghum, sugarcane, asparagus, perennial seed grasses, turf, pastures, pastures, and non-crop lands. Dicamba and methods for preparing dicamba are known in the art. Its herbicidal activity is described in, for example, The Pesticide Manual, the 17th edition, 2016.
[0298] In some aspects, dicamba can be provided as an agriculturally acceptable salt or ester of dicamba. Exemplary agriculturally acceptable salts and esters of dicamba include, but are not limited to, dicamba-diglycolammonium, dicamba-dimethylammonium, dicamba-diethanolamine, dicamba-isopropylammonium, dicamba-methyl, dicamba-ethanolamine, dicamba-potassium, dicamba-sodium, dicamba-triethanolamine, and cambendichlor.
[0299] In some aspects, dicamba can be provided as dicamba-diglycolammonium as shown below.
[0300] Dicamba may be applied to vegetation or areas adjacent to vegetation or to soil or water in an amount sufficient to induce a herbicidal effect to prevent the emergence or growth of vegetation. In some aspects, dicamba is applied to vegetation or an area adjacent to vegetation or to soil or water in an amount to prevent emergence or growth of vegetation: 50 g ai / ha or more, such as 55 g ai / ha or more, 60 g ai / ha or more, 65 g ai / ha or more, 70 g ai / ha or more, 75 g ai / ha or more, 80 g ai / ha or more, 85 g ai / ha or more, 90 g ai / ha or more, 95 g ai / ha or more, 100 g ai / ha or more, 110 g ai / ha or more, 120 g ai / ha or more, 125 g ai / ha or more, 130 g ai / ha or more, 140 g ai / ha or more, 150 g ai / ha or more, 160 g ai / ha or more, 170 g ai / ha or more, 175 g ai / ha or more, 180 g ai / ha or more, 190 g ai / ha or more. g ai / ha or more, 200g ai / ha or more, 210g ai / ha or more, 220g ai / ha or more, 225g ai / ha or more, 230g ai / ha or more, 240g ai / ha or more, 250g ai / ha or more, 260g ai / ha or more, 270g ai / ha or more, 275g ai / ha or more, 280g ai / ha or more, 290g ai / ha or more, 300g ai / ha or more, 310g ai / ha or more, 320g ai / ha or more, 325g ai / ha or more, 330g ai / ha or more, 340g ai / ha or more, 350g ai / ha or more, 360g ai / ha or more, 370g ai / ha or more, 375g ai / ha or more, 380g ai / ha or more, 390g ai / ha or more g ai / ha or more, 400 g ai / ha or more, 425 g ai / ha or more, 450 g ai / ha or more, 475 g ai / ha or more, 500 g ai / ha or more, 525 g ai / ha or more, 550 g ai / ha or more, 560 g ai / ha or more, 570 g ai / ha or more, 575 g ai / ha or more, 580 g ai / ha or more, 590 g ai / ha or more, or 600 g ai / ha or more;In the following amounts: 600g ai / ha or less, such as 590g ai / ha or less, 580g ai / ha or less, 575g ai / ha or less, 570g ai / ha or less, 560g ai / ha or less, 550g ai / ha or less, 525g ai / ha or less, 500g ai / ha or less, 475g ai / ha or less, 450g ai / ha or less, 425g ai / ha or less, 400g ai / ha or less, 390g ai / ha or less, 380g ai / ha or less, 375g ai / ha or less, 370g ai / ha or less, 360g ai / ha or less, 350g ai / ha or less, 340g ai / ha or less, 330g ai / ha or less, 325g ai / ha or less. g ai / ha or less, 320g ai / ha or less, 310g ai / ha or less, 300g ai / ha or less, 290g ai / ha or less, 280g ai / ha or less, 275g ai / ha or less, 270g ai / ha or less, 260g ai / ha or less, 250g ai / ha or less, 240g ai / ha or less, 230g ai / ha or less, 225g ai / ha or less, 220g ai / ha or less, 210g ai / ha or less, 200g ai / ha or less, 190g ai / ha or less, 180g ai / ha or less, 175g ai / ha or less, 170g ai / ha or less, 160g ai / ha or less, 150g ai / ha or less, 140g ai / ha or less g ai / ha or less, 130 g ai / ha or less, 125 g ai / ha or less, 120 g ai / ha or less, 110 g ai / ha or less, 100 g ai / ha or less, 95 g ai / ha or less, 90 g ai / ha or less, 85 g ai / ha or less, 80 g ai / ha or less, 75 g ai / ha or less, 70 g ai / ha or less, 65 g ai / ha or less, 60 g ai / ha or less, or 55 g ai / ha or less; or in an amount ranging from any of the foregoing minimum values to any of the foregoing maximum values, such as 50-600 g ai / ha, 55-150 g ai / ha, 60-310 g ai / ha, 65-190 g ai / ha, 80-560 g ai / ha, 85-300 g ai / ha ai / ha, 100-275g ai / ha, 120-475g ai / ha, 140-390g ai / ha, 150-250gai / ha, or 250-400g ai / ha. ; 2,3,6-TBA
[0301] In some aspects, the synthetic auxin herbicide may include 2,3,6-TBA or an agriculturally acceptable salt or ester thereof. 2,3,6-TBA shown below is a benzoic acid herbicide that provides post-emergence control of certain broadleaf annual and perennial weeds in cereal and grass seed crops. 2,3,6-TBA and methods for preparing 2,3,6-TBA are known in the art. Its herbicidal activity is described, for example, in The Pesticide Manual, Seventeenth Edition, 2016. C. Aryl picolinate
[0302] In some aspects, the composition contains a compound according to Formula I, and (b) fluopyr-butyl, halopyr-butyl, or an agriculturally acceptable salt or ester thereof. Clopidogrel
[0303] In some aspects, the synthetic auxin herbicide may include fluopyridine-butyl or an agriculturally acceptable salt or ester thereof. Fluopyridine-butyl is an aryl picolinic acid that has been described in U.S. Patent 7,314,849 B2. Exemplary uses of fluopyridine-butyl include controlling undesirable vegetation (including grass weeds, broadleaf weeds, and sedge weeds) in a variety of non-crop and farming situations.
[0304] In some aspects, clofopyralid can be provided as an agriculturally acceptable salt or ester of clofopyralid. Exemplary agriculturally acceptable salts and esters of clofopyralid include, but are not limited to, clofopyralid benzyl ester as shown below.
[0305] Haloperidol may be applied to vegetation or areas adjacent to vegetation or to soil or water in an amount sufficient to induce a herbicidal effect to prevent the emergence or growth of vegetation. In some aspects, clofopyralid is applied to vegetation or an area adjacent to vegetation or to soil or water in an amount of 1 g ai / ha or more, such as 2 g ai / ha or more, 3 g ai / ha or more, 4 g ai / ha or more, 5 g ai / ha or more, 6 g ai / ha or more, 7 g ai / ha or more, 8 g ai / ha or more, 9 g ai / ha or more, 10 g ai / ha or more, 12.5 g ai / ha or more, 15 g ai / ha or more, 17.5 g ai / ha or more, 20 g ai / ha or more, 25 g ai / ha or more, 30 g ai / ha or more, 35 g ai / ha or more, 40 g ai / ha or more, 45 g ai / ha or more, 50 g ai / ha or more, 60 g ai / ha or more, 70 g ai / ha or more, 75 g ai / ha or more, 80 g ai / ha or more. g ai / ha or more, 90 g ai / ha or more, 100 g ai / ha or more, 110 g ai / ha or more, 120 g ai / ha or more, 125 g ai / ha or more, 130 g ai / ha or more, 140 g ai / ha or more, 142.5 g ai / ha or more, 145 g ai / ha or more, 147.5 g ai / ha or more, or 149 g ai / ha or more; in amounts of 150 g ai / ha or less, such as 149 g ai / ha or less, 147.5 g ai / ha or less, 145 g ai / ha or less, 142.5 g ai / ha or less, 140 g ai / ha or less, 130 g ai / ha or less, 125 g ai / ha or less, 120 g ai / ha or less, 110 g ai / ha or less, 100 g ai / ha or less ai / ha or less, 90g ai / ha or less, 80g ai / ha or less, 75g ai / ha or less, 70g ai / ha or less, 60g ai / ha or less, 50g ai / ha or less, 45g ai / ha or less, 40g ai / ha or less, 35g ai / ha or less, 30g ai / ha or less, 25g ai / ha or less, 20g ai / ha or less, 17.5g ai / ha or less, 15g ai / ha or less, 12.5g ai / ha or less, 10g ai / ha or less, 9g ai / ha or less, 8g ai / ha or less, 7g ai / ha or less, 6g ai / ha or less, 5g ai / ha or less, 4g ai / ha or less, 3g ai / ha or less, or 2g ai / ha or less; or in an amount ranging from any of the above minimum values to any of the above maximum values, such as 1-150g ai / ha, 2-130g ai / ha, 2-45g ai / ha, 3-70g ai / ha, 4-147.5g ai / ha, 5-100g ai / ha, 6-75g ai / ha, 7-50g ai / ha, 10-149g ai / ha, 20-120g ai / ha, 25-90g ai / ha, 30-60g ai / ha, 50-150g ai / ha, 60-130g ai / ha, or 100-145g ai / ha. . Haloperidol
[0306] In some aspects, the synthetic auxin herbicide can include halauxifen-butyl or an agriculturally acceptable salt or ester thereof.Halauxifen-butyl, shown below, is an arylpicolinic acid herbicide that provides broad spectrum control of broadleaf weeds in cereal crops.
[0307] In some aspects, halauxifen can be provided as an agriculturally acceptable salt or ester of halauxifen. Exemplary agriculturally acceptable salts and esters of halauxifen include but are not limited to halauxifen methyl. In some aspects, halauxifen can be provided as halauxifen methyl as shown below.
[0308] Haloxyfop-butyl may be applied to vegetation or areas adjacent to vegetation or to soil or water in an amount sufficient to induce a herbicidal effect to prevent the emergence or growth of vegetation. In some aspects, haloxifen-butyl is applied to vegetation or an area adjacent to vegetation or to soil or water in an amount of 1 g ai / ha or more, such as 2 g ai / ha or more, 2.5 g ai / ha or more, 3 g ai / ha or more, 4 g ai / ha or more, 5 g ai / ha or more, 6 g ai / ha or more, 7 g ai / ha or more, 8 g ai / ha or more, 9 g ai / ha or more, 10 g ai / ha or more, 12.5 g ai / ha or more, 15 g ai / ha or more, 17.5 g ai / ha or more, 20 g ai / ha or more, 25 g ai / ha or more, 30 g ai / ha or more, 35 g ai / ha or more, 40 g ai / ha or more, 45 g ai / ha or more, 50 g ai / ha or more, 60 g ai / ha or more, 70 g ai / ha or more, 75 g ai / ha or more. g ai / ha or more, 80 g ai / ha or more, 90 g ai / ha or more, 100 g ai / ha or more, 110 g ai / ha or more, 120 g ai / ha or more, 125 g ai / ha or more, 130 g ai / ha or more, 140 g ai / ha or more, 142.5 g ai / ha or more, 145 g ai / ha or more, 147.5 g ai / ha or more, or 149 g ai / ha or more; in amounts of 150 g ai / ha or less, such as 149 g ai / ha or less, 147.5 g ai / ha or less, 145 g ai / ha or less, 142.5 g ai / ha or less, 140 g ai / ha or less, 130 g ai / ha or less, 125 g ai / ha or less, 120 g ai / ha or less, 110 g ai / ha or more ai / ha or less, 100g ai / ha or less, 90g ai / ha or less, 80g ai / ha or less, 75g ai / ha or less, 70g ai / ha or less, 60g ai / ha or less, 50g ai / ha or less, 45g ai / ha or less, 40g ai / ha or less, 35g ai / ha or less, 30g ai / ha or less, 25g ai / ha or less, 20g ai / ha or less, 17.5g ai / ha or less, 15g ai / ha or less, 12.g ai / ha, 5-100g ai / ha, 6-75g ai / ha, 7-50g ai / ha, 10-149g ai / ha, 20-120g ai / ha, 25-90g ai / ha, 30-40g ai / ha, 50-60g ai / ha, 60-75g ai / ha, 70-80g ai / ha, 80-90g ai / ha, 100-110g ai / ha, 20-250g ai / ha, 25-260g ai / ha, 20-270g ai / ha, 25-300g ai / ha, 20-280g ai / ha, 25-300g ai / ha, 25-300g ai / ha, 25-300g ai / ha, 25-300g ai / ha, 25-300g ai / ha, 25-300g ai / ha, 25-300g ai / ha, 25-300g ai / ha, ai / ha, 30-60g ai / ha, 50-150g ai / ha, 60-130gai / ha, or 100-145g ai / ha. . Pyridine carboxylate
[0309] In some aspects, the composition contains a compound according to Formula I, and (b) aminopyralid, clopyralid, fluazifop, picloram, triclopyr, or an agriculturally acceptable salt or ester thereof. Amipedic acid
[0310] In some aspects, the synthetic auxin herbicide may include aminopyralid or an agriculturally acceptable salt or ester thereof. Aminopyralid is a compound according to Formula I that provides pre-emergence and post-emergence control of certain annual and perennial broadleaf weeds in grasslands. Aminopyralid and methods for preparing aminopyralid are known in the art. Its herbicidal activity is described in The Pesticide Manual, Seventeenth Edition, 2016.
[0311] In some aspects, aminopyralid can be provided as an agriculturally acceptable salt or ester of aminopyralid. Exemplary agriculturally acceptable salts and esters of aminopyralid include, but are not limited to, aminopyralid-triisopropanolammonium (TIPA), for example, as shown below.
[0312] Ampyralid may be applied to vegetation or areas adjacent to vegetation or to soil or water in an amount sufficient to induce a herbicidal effect to prevent the emergence or growth of vegetation. In some aspects, aminopyralid is applied to vegetation or to an area adjacent to vegetation or to soil or water in an amount of 1 g ai / ha or more, such as 2 g ai / ha or more, 2.5 g ai / ha or more, 3 g ai / ha or more, 4 g ai / ha or more, 5 g ai / ha or more, 6 g ai / ha or more, 7 g ai / ha or more, 8 g ai / ha or more, 9 g ai / ha or more, 10 g ai / ha or more, 12.5 g ai / ha or more, 15 g ai / ha or more, 17.5 g ai / ha or more, 20 g ai / ha or more, 25 g ai / ha or more, 30 g ai / ha or more, 35 g ai / ha or more, 40 g ai / ha or more, 45 g ai / ha or more, 50 g ai / ha or more, 60 g ai / ha or more, 70 g ai / ha or more, 75 g ai / ha or more. g ai / ha or more, 80 g ai / ha or more, 90 g ai / ha or more, 100 g ai / ha or more, 110 g ai / ha or more, 120 g ai / ha or more, 125 g ai / ha or more, 130 g ai / ha or more, 140 g ai / ha or more, 142.5 g ai / ha or more, 145 g ai / ha or more, 147.5 g ai / ha or more, or 149 g ai / ha or more; in amounts of 150 g ai / ha or less, such as 149 g ai / ha or less, 147.5 g ai / ha or less, 145 g ai / ha or less, 142.5 g ai / ha or less, 140 g ai / ha or less, 130 g ai / ha or less, 125 g ai / ha or less, 120 g ai / ha or less, 110 g ai / ha or more ai / ha or less, 100g ai / ha or less, 90g ai / ha or less, 80g ai / ha or less, 75g ai / ha or less, 70g ai / ha or less, 60g ai / ha or less, 50g ai / ha or less, 45g ai / ha or less, 40g ai / ha or less, 35g ai / ha or less, 30g ai / ha or less, 25g ai / ha or less, 20g ai / ha or less, 17.5g ai / ha or less, 15g ai / ha or less, 12.g ai / ha, 5-100g ai / ha, 6-75g ai / ha, 7-50g ai / ha, 10-149g ai / ha, 20-120g ai / ha, 25-90g ai / ha, 30-40g ai / ha, 50-60g ai / ha, 60-75g ai / ha, 70-80g ai / ha, 80-90g ai / ha, 100-110g ai / ha, 20-250g ai / ha, 25-260g ai / ha, 20-270g ai / ha, 25-300g ai / ha, 20-280g ai / ha, 25-300g ai / ha, 25-300g ai / ha, 25-300g ai / ha, 25-300g ai / ha, 25-300g ai / ha, 25-300g ai / ha, 25-300g ai / ha, 25-300g ai / ha, ai / ha, 30-60g ai / ha, 50-150g ai / ha, 60-130gai / ha, or 100-145g ai / ha. . Clopyralid
[0313] In some aspects, the synthetic auxin herbicide may include clopyralid or an agriculturally acceptable salt or ester thereof. Clopyralid, as shown below, is a compound according to Formula I that provides post-emergence control of many annual and perennial broadleaf weeds in sugar beets, fodder beets, rapeseed, corn, cereals, Brassicas, onions, leeks, strawberries, flax, grasslands, and non-crop lands. Clopyralid and methods for preparing clopyralid are known in the art. Its herbicidal activity is described, for example, in The Pesticide Manual, Seventeenth Edition, 2016.
[0314] In some aspects, clopyralid can be provided as an agriculturally acceptable salt or ester of clopyralid. Exemplary agriculturally acceptable salts and esters of clopyralid include, but are not limited to, clopyralid-methyl, clopyralid-potassium, clopyralid-tri(2-hydroxypropyl)ammonium, and clopyralid-ethanolamine as shown below.
[0315] Clopyralid may be applied to vegetation or areas adjacent to vegetation or to soil or water in an amount sufficient to induce a herbicidal effect to prevent the emergence or growth of vegetation. In some aspects, clopyralid is applied to vegetation or an area adjacent to vegetation or to soil or water in an amount to prevent emergence or growth of vegetation: 25 g ai / ha or more, such as 30 g ai / ha or more, 35 g ai / ha or more, 40 g ai / ha or more, 45 g ai / ha or more, 50 g ai / ha or more, 55 g ai / ha or more, 60 g ai / ha or more, 65 g ai / ha or more, 70 g ai / ha or more, 75 g ai / ha or more, 80 g ai / ha or more, 85 g ai / ha or more, 90 g ai / ha or more, 95 g ai / ha or more, 100 g ai / ha or more, 110 g ai / ha or more, 120 g ai / ha or more, 125 g ai / ha or more, 130 g ai / ha or more, 140 g ai / ha or more, 150 g ai / ha or more. g ai / ha or more, 160g ai / ha or more, 170g ai / ha or more, 175g ai / ha or more, 180g ai / ha or more, 190g ai / ha or more, 200g ai / ha or more, 210g ai / ha or more, 220g ai / ha or more, 225g ai / ha or more, 230g ai / ha or more, 240g ai / ha or more, 250g ai / ha or more, 260g ai / ha or more, 270g ai / ha or more, 275g ai / ha or more, 280g ai / ha or more, 290g ai / ha or more, 300g ai / ha or more, 310g ai / ha or more, 320g ai / ha or more, 325g ai / ha or more, 330g ai / ha or more, 340g ai / ha or more, 350g ai / ha or more ai / ha or more, 360g ai / ha or more, 370g ai / ha or more, 375g ai / ha or more, 380g ai / ha or more, or 390g ai / ha or more;In amounts such as 400 g ai / ha or less, such as 390 g ai / ha or less, 380 g ai / ha or less, 375 g ai / ha or less, 370 g ai / ha or less, 360 g ai / ha or less, 350 g ai / ha or less, 340 g ai / ha or less, 330 g ai / ha or less, 325 g ai / ha or less, 320 g ai / ha or less, 310 g ai / ha or less, 300 g ai / ha or less, 290 g ai / ha or less, 280 g ai / ha or less, 275 g ai / ha or less, 270 g ai / ha or less, 260 g ai / ha or less, 250 g ai / ha or less, 240 g ai / ha or less, 230 g ai / ha or less, 225 g ai / ha or less g ai / ha or less, 220 g ai / ha or less, 210 g ai / ha or less, 200 g ai / ha or less, 190 g ai / ha or less, 180 g ai / ha or less, 175 g ai / ha or less, 170 g ai / ha or less, 160 g ai / ha or less, 150 g ai / ha or less, 140 g ai / ha or less, 130 g ai / ha or less, 125 g ai / ha or less, 120 g ai / ha or less, 110 g ai / ha or less, 100 g ai / ha or less, 95 g ai / ha or less, 90 g ai / ha or less, 85 g ai / ha or less, 80 g ai / ha or less, 75 g ai / ha or less, 70 g ai / ha or less, 65 g ai / ha or less, 60 g ai / ha or less ai / ha or less, or 55g ai / ha or less, 50g ai / ha or less, 45g ai / ha or less, 40g ai / ha or less, 35g ai / ha or less, or 30g ai / ha or less; or in an amount ranging from any of the above minimum values to any of the above maximum values, such as 25-400g ai / ha, 55-150g ai / ha, 60-310g ai / ha, 65-190g ai / ha, 80-260g ai / ha, 85-300g ai / ha, 100-275g ai / ha, 120-330g ai / ha, 140-390g ai / ha, 150-250g ai / ha, or 30-400g ai / ha. ; Flupirox
[0316] In some aspects, synthetic auxin herbicides may include fluroxypyr or its agriculturally acceptable salt or ester. Fluroxypyr as shown below is a compound according to formula I that provides post-emergence control of certain broadleaf weeds in small grain crops, pastures, grasslands, orchards, plantation crops, corn and woodlands. Fluroxypyr and methods for preparing fluroxypyr are known in the art. Its herbicidal activity is described in, for example, The Pesticide Manual, 17th edition, 2016.
[0317] In some aspects, fluroxypyr can be provided as an agriculturally acceptable salt or ester of fluroxypyr. Exemplary agriculturally acceptable salts and esters of fluroxypyr include, but are not limited to, fluroxypyr-2-butoxy-1-methylethyl (fluroxypyr-butoxymethylethyl (butometyl)) and fluroxypyr-methylheptyl (fluroxypyr-MHE). In some aspects, fluroxypyr can be provided as fluroxypyr-methylheptyl (fluroxypyr-MHE) as shown below.
[0318] Flupyr may be applied to vegetation or areas adjacent to vegetation or to soil or water in an amount sufficient to induce a herbicidal effect to prevent the emergence or growth of vegetation. In some aspects, clofopyralid is applied to vegetation or an area adjacent to vegetation or to soil or water in an amount to prevent emergence or growth of vegetation: 35 g ai / ha or more, such as 40 g ai / ha or more, 45 g ai / ha or more, 50 g ai / ha or more, 55 g ai / ha or more, 60 g ai / ha or more, 65 g ai / ha or more, 70 g ai / ha or more, 75 g ai / ha or more, 80 g ai / ha or more, 85 g ai / ha or more, 90 g ai / ha or more, 95 g ai / ha or more, 100 g ai / ha or more, 110 g ai / ha or more, 120 g ai / ha or more, 125 g ai / ha or more, 130 g ai / ha or more, 140 g ai / ha or more, 150 g ai / ha or more, 160 g ai / ha or more, 170 g ai / ha or more g ai / ha or more, 175g ai / ha or more, 180g ai / ha or more, 190g ai / ha or more, 200g ai / ha or more, 210g ai / ha or more, 220g ai / ha or more, 225g ai / ha or more, 230g ai / ha or more, 240g ai / ha or more, 250g ai / ha or more, 260g ai / ha or more, 270g ai / ha or more, 275g ai / ha or more, 280g ai / ha or more, 290g ai / ha or more, 300g ai / ha or more, 310g ai / ha or more, 320g ai / ha or more, 325g ai / ha or more, 330g ai / ha or more, 340g ai / ha or more, 350g ai / ha or more, 360g ai / ha or more, 370g ai / ha or more ai / ha or more, 375g ai / ha or more, 380g ai / ha or more, or 390g ai / ha or more;In the following amounts: 400 g ai / ha or less, such as 390 g ai / ha or less, 380 g ai / ha or less, 375 g ai / ha or less, 370 g ai / ha or less, 360 g ai / ha or less, 350 g ai / ha or less, 340 g ai / ha or less, 330 g ai / ha or less, 325 g ai / ha or less, 320 g ai / ha or less, 310 g ai / ha or less, 300 g ai / ha or less, 290 g ai / ha or less, 280 g ai / ha or less, 275 g ai / ha or less, 270 g ai / ha or less, 260 g ai / ha or less, 250 g ai / ha or less, 240 g ai / ha or less, 230 g ai / ha or less, 225 g ai / ha or less g ai / ha or less, 220 g ai / ha or less, 210 g ai / ha or less, 200 g ai / ha or less, 190 g ai / ha or less, 180 g ai / ha or less, 175 g ai / ha or less, 170 g ai / ha or less, 160 g ai / ha or less, 150 g ai / ha or less, 140 g ai / ha or less, 130 g ai / ha or less, 125 g ai / ha or less, 120 g ai / ha or less, 110 g ai / ha or less, 100 g ai / ha or less, 95 g ai / ha or less, 90 g ai / ha or less, 85 g ai / ha or less, 80 g ai / ha or less, 75 g ai / ha or less, 70 g ai / ha or less, 65 g ai / ha or less, 60 g ai / ha or less ai / ha or less, 55g ai / ha or less, 50g ai / ha or less, 45g ai / ha or less, 40g ai / ha or less, or 35g ai / ha or less; or in an amount ranging from any of the above minimum values to any of the above maximum values, such as 35-400g ai / ha, 55-150g ai / ha, 60-310g ai / ha, 45-190g ai / ha, 80-260g ai / ha, 85-300g ai / ha, 100-275g ai / ha, 120-330g ai / ha, 140-390g ai / ha, 150-250g ai / ha, or 250-400g ai / ha. ; piclotradine
[0319] In some aspects, the synthetic auxin herbicide may include picloram or an agriculturally acceptable salt or ester thereof. Picloram is a compound according to Formula I that provides management of unwanted vegetation in pastures, grasslands, woodlands, and non-crop lands and right-of-way locations. Picloram and methods for preparing picloram are known in the art. Its herbicidal activity is described in The Pesticide Manual, Seventeenth Edition, 2016.
[0320] In some respects, picloram can be provided as an agriculturally acceptable salt or ester of picloram. Exemplary agriculturally acceptable salts and esters of picloram include but are not limited to picloram-dimethylammonium, picloram-isooctyl, picloram-potassium, picloram-triethylammonium, picloram-triisopropanol ammonium (TIPA), picloram-triisopropylammonium and picloram-trolamine (triethanolammonium). In some respects, picloram can be provided as picloram-potassium as shown below.
[0321] In some aspects, picloram can be provided as picloram-TIPA as shown below.
[0322] Pilosamide may be applied to vegetation or areas adjacent to vegetation or to soil or water in an amount sufficient to induce a herbicidal action to prevent the emergence or growth of vegetation. In some aspects, picloram is applied to vegetation or an area adjacent to vegetation or to soil or water in an amount of 10 g ai / ha or more, such as 12 g ai / ha or more, 14 g ai / ha or more, 15 g ai / ha or more, 16 g ai / ha or more, 18 g ai / ha or more, 20 g ai / ha or more, 25 g ai / ha or more, 30 g ai / ha or more, 35 g ai / ha or more, 40 g ai / ha or more, 45 g ai / ha or more, 50 g ai / ha or more, 60 g ai / ha or more, 70 g ai / ha or more, 75 g ai / ha or more, 80 g ai / ha or more, 90 g ai / ha or more, 100 g ai / ha or more, 125 g ai / ha or more, 150 g ai / ha or more, 175 g ai / ha or more, 200 g ai / ha or more g ai / ha or more, 225 g ai / ha or more, 250 g ai / ha or more, 275 g ai / ha or more, 300 g ai / ha or more, 325 g ai / ha or more, 350 g ai / ha or more, 375 g ai / ha or more, 400 g ai / ha or more, 450 g ai / ha or more, 500 g ai / ha or more, 550 g ai / ha or more, 600 g ai / ha or more, 650 g ai / ha or more, 700 g ai / ha or more, 750 g ai / ha or more, 800 g ai / ha or more, 850 g ai / ha or more, 900 g ai / ha or more, 950 g ai / ha or more, 1000 g ai / ha or more, 1100 g ai / ha or more, 1200 g ai / ha or more, 1300 g ai / ha or more, 1400 g ai / ha or more g ai / ha or more, 1500 g ai / ha or more, 1600 g ai / ha or more, 1700 g ai / ha or more, 1800 g ai / ha or more, 1900 g ai / ha or more, 2000 g ai / ha or more, 2050 g ai / ha or more, 2100 g ai / ha or more, 2150 g ai / ha or more, 2200 g ai / ha or more, or 2220 g ai / ha or more;In the following amounts: 22400g ai / ha or less, such as 2220g ai / ha or less, 2200g ai / ha or less, 2150g ai / ha or less, 2100g ai / ha or less, 2050g ai / ha or less, 2000g ai / ha or less, 1900g ai / ha or less, 1800g ai / ha or less, 1700g ai / ha or less, 1600g ai / ha or less, 1500g ai / ha or less, 1400g ai / ha or less, 1300g ai / ha or less, 1200g ai / ha or less, 1100g ai / ha or less, 1000g ai / ha or less, 950g ai / ha or less, 900g ai / ha or less, 850g ai / ha or less, 800g ai / ha or less. g ai / ha or less, 750 g ai / ha or less, 700 g ai / ha or less, 650 g ai / ha or less, 600 g ai / ha or less, 550 g ai / ha or less, 500 g ai / ha or less, 450 g ai / ha or less, 400 g ai / ha or less, 375 g ai / ha or less, 350 g ai / ha or less, 325 g ai / ha or less, 300 g ai / ha or less, 275 g ai / ha or less, 250 g ai / ha or less, 225 g ai / ha or less, 200 g ai / ha or less, 175 g ai / ha or less, 150 g ai / ha or less, 125 g ai / ha or less, 100 g ai / ha or less, 90 g ai / ha or less, 80 g ai / ha or less. ai / ha or less, 75g ai / ha or less, 70g ai / ha or less, 60g ai / ha or less, 50g ai / ha or less, 45g ai / ha or less, 40g ai / ha or less, 35g ai / ha or less, 30g ai / ha or less, 25g ai / ha or less, 20g ai / ha or less, 18g ai / ha or less, 16g ai / ha or less, 15g ai / ha or less, 14g ai / ha or less, or 12g ai / ha or less;or an amount ranging from any of the above minimum values to any of the above maximum values, such as 10-2240 g ai / ha, 12-1500 g ai / ha, 14-2100 g ai / ha, 15-900 g ai / ha, 18-1600 g ai / ha, 30-1200 g ai / ha, 50-275 g ai / ha, 70-1000 g ai / ha, 100-2220 g ai / ha, 250-1300 g ai / ha, 450-2000 g ai / ha, or 500-1900 g ai / ha. ; Triclopyr
[0323] In some aspects, the synthetic auxin herbicide may include triclopyr or an agriculturally acceptable salt or ester thereof. Triclopyr is a compound according to Formula I that provides control of woody and broadleaf weed species in grasslands, pastures, industrial areas, coniferous forests, rice, and planted crops. Triclopyr and methods for preparing triclopyr are known in the art. Its herbicidal activity is described in The Pesticide Manual, Seventeenth Edition, 2016.
[0324] In some aspects, triclopyr can be provided as an agriculturally acceptable salt or ester of triclopyr. Exemplary agriculturally acceptable salts and esters of triclopyr include, but are not limited to, for example, triclopyr-triethylammonium (TEA), triclopyr choline, and triclopyr-butoxyethyl (butoxyethyl or BEE). In some aspects, triclopyr can be provided as triclopyr-triethylammonium (TEA) as shown below.
[0325] In some aspects, triclopyr can be provided as triclopyr-choline as shown below.
[0326] In some aspects, triclopyr can be provided as triclopyr-BEE as shown...
Claims
1. A compound according to formula I: Where X is: Wherein R1 is independently hydrogen, C1-C 16 Alkyl, C1-C 16 Heteroalkyl, C5-C 10 Aryl, C5-C 10 heteroaryl, alkylcarbonyl, alkoxycarbonyl, aryloxycarbonyl, heteroaryloxycarbonyl, mono- or di-substituted alkylaminocarbonyl, mono- or di-substituted arylaminocarbonyl, mono- or di-substituted heteroarylaminocarbonyl, alkylthiocarbonyl, arylthiocarbonyl, or heteroarylthiocarbonyl; R2 is independently hydrogen, C1-C 16 Alkyl, C1-C 16 Heteroalkyl, C5-C 10 Aryl, C5-C 10 heteroaryl, alkylcarbonyl, alkoxycarbonyl, aryloxycarbonyl, heteroaryloxycarbonyl, mono- or di-substituted alkylaminocarbonyl, mono- or di-substituted arylaminocarbonyl, mono- or di-substituted heteroarylaminocarbonyl, alkylthiocarbonyl, arylthiocarbonyl, heteroarylthiocarbonyl; R3 is independently hydrogen, C1-C 16 Alkyl, C1-C 16 Heteroalkyl, C5-C 10 Aryl, C5-C 10 heteroaryl, alkylcarbonyl, alkoxycarbonyl, aryloxycarbonyl, heteroaryloxycarbonyl, mono- or di-substituted alkylaminocarbonyl, mono- or di-substituted arylaminocarbonyl, mono- or di-substituted heteroarylaminocarbonyl, alkylthiocarbonyl, arylthiocarbonyl, heteroarylthiocarbonyl; R1 and R2 together form a substituted double bond, a 3-membered ring, a 4-membered ring, a 5-membered ring, a 6-membered ring, or a 7-membered ring; A is independently O, Si, NR, and S(O) m ; A2 is independently O, N, S(O) m , substituted alkyl, heteroalkyl, alkenyl, alkynyl, aryl, heteroaryl, alkylaryl, alkylheteroaryl; Y is independently O, N, S; Z is independently O, N, S(O) m , substituted alkyl, alkenyl, alkynyl, aryl, heteroaryl, alkylcarbonyl, alkoxycarbonyl, aryloxycarbonyl, heteroaryloxycarbonyl, mono- or di-substituted alkylaminocarbonyl, mono- or di-substituted arylaminocarbonyl, mono- or di-substituted heteroarylaminocarbonyl, alkylthiocarbonyl, arylthiocarbonyl, heteroarylthiocarbonyl, -N=R4R5, R4 and R5 are independently substituted amino, alkoxy, alkyl, heteroalkyl, aryl, heteroaryl; n is 1, 2, or 3; and m is 0, 1, or 2; The compounds exhibit pesticidal activity, provided that the compound is not 2,4-D isooctyl ester.
2. The compound according to claim 1, wherein X is: in R1 is independently hydrogen, C1-C 16 Alkyl, C1-C 16 Heteroalkyl, C5-C 10 Aryl, C5-C 10 heteroaryl, alkylcarbonyl, alkoxycarbonyl, aryloxycarbonyl, heteroaryloxycarbonyl, mono- or di-substituted alkylaminocarbonyl, mono- or di-substituted arylaminocarbonyl, mono- or di-substituted heteroarylaminocarbonyl, alkylthiocarbonyl, arylthiocarbonyl, or heteroarylthiocarbonyl; and R2 is independently hydrogen, C1-C 16 Alkyl, C1-C 16 Heteroalkyl, C5-C 10 Aryl, C5-C 10 heteroaryl, alkylcarbonyl, alkoxycarbonyl, aryloxycarbonyl, heteroaryloxycarbonyl, mono- or di-substituted alkylaminocarbonyl, mono- or di-substituted arylaminocarbonyl, mono- or di-substituted heteroarylaminocarbonyl, alkylthiocarbonyl, arylthiocarbonyl, heteroarylthiocarbonyl.
3. The compound according to claim 1, wherein X is: in R3 is independently hydrogen, C1-C 16 Alkyl, C1-C 16 Heteroalkyl, C5-C 10 Aryl, C5-C 10 heteroaryl, alkylcarbonyl, alkoxycarbonyl, aryloxycarbonyl, heteroaryloxycarbonyl, mono- or di-substituted alkylaminocarbonyl, mono- or di-substituted arylaminocarbonyl, mono- or di-substituted heteroarylaminocarbonyl, alkylthiocarbonyl, arylthiocarbonyl, heteroarylthiocarbonyl; A is independently O, Si, NR, and S(O) m , substituted alkyl, alkenyl, alkynyl, aryl, heteroaryl, alkylcarbonyl, alkoxycarbonyl, aryloxycarbonyl, heteroaryloxycarbonyl, mono- or di-substituted alkylaminocarbonyl, mono- or di-substituted arylaminocarbonyl, mono- or di-substituted heteroarylaminocarbonyl, alkylthiocarbonyl, arylthiocarbonyl, heteroarylthiocarbonyl, -N=R4R5, R4 and R5 are independently substituted amino, alkoxy, alkyl, heteroalkyl, aryl, heteroaryl; and m is 0, 1, or 2.
4. The compound according to claim 1, wherein X is: in R2 is independently hydrogen, C1-C 16 Alkyl, C1-C 16 Heteroalkyl, C5-C 10 Aryl, C5-C 10 heteroaryl, alkylcarbonyl, alkoxycarbonyl, aryloxycarbonyl, heteroaryloxycarbonyl, mono- or di-substituted alkylaminocarbonyl, mono- or di-substituted arylaminocarbonyl, mono- or di-substituted heteroarylaminocarbonyl, alkylthiocarbonyl, arylthiocarbonyl, heteroarylthiocarbonyl.
5. The compound according to claim 1, wherein X is:
6. The compound according to claim 1, wherein X is: in A2 is independently O, N, S(O) m , substituted alkyl, heteroalkyl, alkenyl, alkynyl, aryl, heteroaryl, alkylaryl, alkylheteroaryl; Y is independently O, N, S; Z is independently O, N, S(O) m , substituted alkyl, alkenyl, alkynyl, aryl, heteroaryl, alkylcarbonyl, alkoxycarbonyl, aryloxycarbonyl, heteroaryloxycarbonyl, mono- or di-substituted alkylaminocarbonyl, mono- or di-substituted arylaminocarbonyl, mono- or di-substituted heteroarylaminocarbonyl, alkylthiocarbonyl, arylthiocarbonyl, heteroarylthiocarbonyl, -N=R4R5, R4 and R5 are independently substituted amino, alkoxy, alkyl, heteroalkyl, aryl, heteroaryl; n is 1, 2, or 3; and m is 0, 1, or 2.
7. The compound according to claim 2, wherein The compound is according to the following formula A1: in R1 and R2 are independently hydrogen, C1-C 16 Alkyl, C1-C 16 Heteroalkyl, C5-C 10 Aryl, C5-C 10 heteroaryl, alkylcarbonyl, alkoxycarbonyl, aryloxycarbonyl, heteroaryloxycarbonyl, mono- or di-substituted alkylaminocarbonyl, mono- or di-substituted arylaminocarbonyl, mono- or di-substituted heteroarylaminocarbonyl, alkylthiocarbonyl, arylthiocarbonyl, heteroarylthiocarbonyl, mono- or di-substituted alkylamino, mono- or di-substituted arylamino, mono- or di-substituted heteroarylamino, alkoxy, arylalkoxy, heteroarylalkoxy, alkylthio, arylthio, heteroarylthio.
8. The compound according to claim 2, wherein The compound is according to the following formula A2: in R1 is independently hydrogen, C1-C 16 Alkyl, C1-C 16 Heteroalkyl, C5-C 10 Aryl, C5-C 10 heteroaryl, alkylcarbonyl, alkoxycarbonyl, aryloxycarbonyl, heteroaryloxycarbonyl, mono- or di-substituted alkylaminocarbonyl, mono- or di-substituted arylaminocarbonyl, mono- or di-substituted heteroarylaminocarbonyl, alkylthiocarbonyl, arylthiocarbonyl, or heteroarylthiocarbonyl; and R2 is independently hydrogen, C1-C 16 Alkyl, C1-C 16 Heteroalkyl, C5-C 10 Aryl, C5-C 10 heteroaryl, alkylcarbonyl, alkoxycarbonyl, aryloxycarbonyl, heteroaryloxycarbonyl, mono- or di-substituted alkylaminocarbonyl, mono- or di-substituted arylaminocarbonyl, mono- or di-substituted heteroarylaminocarbonyl, alkylthiocarbonyl, arylthiocarbonyl, heteroarylthiocarbonyl.
9. The compound according to claim 2, wherein The compound is according to the following formula A3: in R1 is independently hydrogen, C1-C 16 Alkyl, C1-C 16 Heteroalkyl, C5-C 10 Aryl, C5-C 10 heteroaryl, alkylcarbonyl, alkoxycarbonyl, aryloxycarbonyl, heteroaryloxycarbonyl, mono- or di-substituted alkylaminocarbonyl, mono- or di-substituted arylaminocarbonyl, mono- or di-substituted heteroarylaminocarbonyl, alkylthiocarbonyl, arylthiocarbonyl, or heteroarylthiocarbonyl; and R2 is independently hydrogen, C1-C 16 Alkyl, C1-C 16 Heteroalkyl, C5-C 10 Aryl, C5-C 10 heteroaryl, alkylcarbonyl, alkoxycarbonyl, aryloxycarbonyl, heteroaryloxycarbonyl, mono- or di-substituted alkylaminocarbonyl, mono- or di-substituted arylaminocarbonyl, mono- or di-substituted heteroarylaminocarbonyl, alkylthiocarbonyl, arylthiocarbonyl, heteroarylthiocarbonyl.
10. The compound according to claim 2, wherein The compound is according to the following formula A4: in R1 is independently hydrogen, C1-C 16 Alkyl, C1-C 16 Heteroalkyl, C5-C 10 Aryl, C5-C 10 heteroaryl, alkylcarbonyl, alkoxycarbonyl, aryloxycarbonyl, heteroaryloxycarbonyl, mono- or di-substituted alkylaminocarbonyl, mono- or di-substituted arylaminocarbonyl, mono- or di-substituted heteroarylaminocarbonyl, alkylthiocarbonyl, arylthiocarbonyl, or heteroarylthiocarbonyl.
11. The compound according to claim 2, wherein The compound is selected from the group consisting of: A1, A2, A3, A4, A5, A6, A7, A8, A9, A10, A11, A12, A13, A14, A15, A16, A17, A18, A19, A20, A21, A22, A23, A24, A25, A26, A27, A28, A29, A30, A31, A32, A33, A34, A35, A36, A37, A38, A39, A40, and A41.
12. The compound according to claim 6, wherein The compound is according to the following formula B1:
13. The compound of claim 6, selected from the group consisting of compounds Bl, B2, B3, B4, B5, B6, B7, B8, B9, B10, B11, B12, B13, B14, and B15.
14. The compound according to claim 13, wherein The compound is selected from the group consisting of:
15. The compound according to claim 5, wherein The compound is according to the following formula C: in A is independently C; R2 is independently hydrogen, C1-C 16 Alkyl, C1-C 16 Heteroalkyl, C5-C 10 Aryl, C5-C 10 heteroaryl, alkylcarbonyl, alkoxycarbonyl, aryloxycarbonyl, heteroaryloxycarbonyl, mono- or di-substituted alkylaminocarbonyl, mono- or di-substituted arylaminocarbonyl, mono- or di-substituted heteroarylaminocarbonyl, alkylthiocarbonyl, arylthiocarbonyl, heteroarylthiocarbonyl.
16. The compound according to claim 2, wherein The compound is according to the following formula D: in R1 and R2 are independently hydrogen, C1-C 16 Alkyl, C1-C 16 Heteroalkyl, C5-C 10 Aryl, C5-C 10 heteroaryl, alkylcarbonyl, alkoxycarbonyl, aryloxycarbonyl, heteroaryloxycarbonyl, mono- or di-substituted alkylaminocarbonyl, mono- or di-substituted arylaminocarbonyl, mono- or di-substituted heteroarylaminocarbonyl, alkylthiocarbonyl, arylthiocarbonyl, heteroarylthiocarbonyl, alkylsulfonyl, arylsulfonyl, heteroarylsulfonyl, alkoxysulfonyl, alkylaminosulfonyl, arylaminosulfonyl, heteroarylaminosulfonyl.
17. The compound according to claim 3, wherein The compound is: in R3 is independently hydrogen, C1-C 16 Alkyl, C1-C 16 Heteroalkyl, C5-C 10 Aryl, C5-C 10 heteroaryl, alkylcarbonyl, alkoxycarbonyl, aryloxycarbonyl, heteroaryloxycarbonyl, mono- or di-substituted alkylaminocarbonyl, mono- or di-substituted arylaminocarbonyl, mono- or di-substituted heteroarylaminocarbonyl, alkylthiocarbonyl, arylthiocarbonyl, heteroarylthiocarbonyl; and A is independently O, Si, or NR1, S(O)n--where n=0, 1, 2, and R3 is independently hydrogen, C1-C 16 Alkyl, C1-C 16 Heteroalkyl, C5-C 10 Aryl, C5-C 10 heteroaryl, alkylcarbonyl, alkoxycarbonyl, aryloxycarbonyl, heteroaryloxycarbonyl, mono- or di-substituted alkylaminocarbonyl, mono- or di-substituted arylaminocarbonyl, mono- or di-substituted heteroarylaminocarbonyl, alkylthiocarbonyl, arylthiocarbonyl, heteroarylthiocarbonyl.
18. The compound according to claim 2, wherein The compound is: Wherein R2 is independently hydrogen, C1-C 16 Alkyl, C1-C 16 Heteroalkyl, C5-C 10 Aryl, C5-C 10 heteroaryl, alkylcarbonyl, alkoxycarbonyl, aryloxycarbonyl, heteroaryloxycarbonyl, mono- or di-substituted alkylaminocarbonyl, mono- or di-substituted arylaminocarbonyl, mono- or di-substituted heteroarylaminocarbonyl, alkylthiocarbonyl, arylthiocarbonyl, heteroarylthiocarbonyl, alkylsulfonyl, arylsulfonyl, heteroarylsulfonyl, alkoxysulfonyl, alkylaminosulfonyl, arylaminosulfonyl, heteroarylaminosulfonyl.
19. The compound according to claim 16, wherein The compound is:
20. The compound according to claim 1, wherein The compound is selected from the group consisting of: D1, D2, D3, D4, D5, D6, D7, D8, D9, D10, D11, D12, D13, D14, D15, D16, D17, D18, D19, D20, D21, D22, D23, D24, D25, D26, D27, D28, D29, D30, D31, D32, and D33.
21. The compound according to claim 4, wherein The compound is according to the following formula E: in R2 is independently hydrogen, C1-C 16 Alkyl, C1-C 16 Heteroalkyl, C5-C 10 Aryl, C5-C 10 heteroaryl, alkylcarbonyl, alkoxycarbonyl, aryloxycarbonyl, heteroaryloxycarbonyl, mono- or di-substituted alkylaminocarbonyl, mono- or di-substituted arylaminocarbonyl, mono- or di-substituted heteroarylaminocarbonyl, alkylthiocarbonyl, arylthiocarbonyl, heteroarylthiocarbonyl.
22. The compound according to claim 18, wherein The compound is selected from the group consisting of:
23. The compound according to claim 1, wherein The compounds are the compounds listed in Table 1: Pesticide compounds.
24. A compound according to any one of the preceding claims, wherein The pesticidal activity is herbicidal activity.
25. A composition comprising: a first herbicide, wherein the first herbicide is a compound according to any one of claims 1-24; and Second herbicide.
26. The composition according to claim 25, wherein The second herbicide is selected from the group consisting of acetolactate synthase (ALS), acetohydroxyacid synthase (AHAS) inhibitors, photosystem II inhibitors, acetyl-CoA carboxylase (ACCase) inhibitors, synthetic auxins, auxin transport inhibitors, photosystem I inhibitors, 5-enolpyruvylshikimate-3-phosphate (EPSP) synthase inhibitors, glutamine synthase inhibitors, microtubule assembly inhibitors, mitosis inhibitors, very long chain fatty acids (VLCFA) inhibitors, fatty acid and lipid synthesis inhibitors, protoporphyrinogen oxidase (PPO) inhibitors, carotenoid biosynthesis inhibitors, phytoene dehydrogenase (PDS) inhibitors, 4-hydroxyphenylpyruvate dioxygenase (HPPD) inhibitors, cellulose biosynthesis inhibitors, herbicides with multiple modes of action, and unclassified herbicides.
27. The composition according to claim 25, wherein The first herbicide is selected from the group consisting of:
28. The composition according to claim 25 or 27, wherein The second herbicide is a protoporphyrinogen oxidase (PPO) inhibitor.
29. The composition according to claim 28, wherein The second herbicide is a protoporphyrinogen oxidase (PPO) inhibitor selected from the group consisting of trifluorfen, azopyralid, bispyribac, cypermethrin, fluazifop-butyl, foramsulfuron, methoxyfenoxate, indolone oxalic acid, isopropylpyraclostrobin, flupyridazine oxalic acid, flufenoxate, fluazifop-butyl, flufenoxate, fluazifop-butyl, flufenoxate, lactofen, oxadiazine, oxadiazine, oxyfluorfen, cypermethrin, fluazifop-butyl, flufenoxate, lactofen, oxadiazine, oxadiazine, oxyfluorfen, cypermethrin, fluazifop-butyl, cypermethrin, chlorpyrifos, chlorpyrifos, chlorpyrifos, sulfamethoxam, thiamethoxam, flusulfuron-butyl, trifluorfen, an agriculturally acceptable salt thereof, or a combination thereof.
30. The composition according to claim 25 or 27, wherein The second herbicide is a 4-hydroxyphenyl-pyruvate-dioxygenase (HPPD) inhibitor selected from the group consisting of benzobicyclon, pyraclostrobin, flupyraclostrobin, fenquinolone, isoxaclostrobin, isoxaclostrobin, lancotrione, mesotrione, pyraclostrobin, sulfaquinoxaline, pyraclostrobin, pyrazoline, pyrazoline, benzylpyrazone, sulfaquinoxaline, furansulfuron, tampoxolone, tobiraterone, pyraclostrobin or their agriculturally acceptable salts or esters, and combinations thereof.
31. The composition according to claim 25 or 27, wherein The second herbicide is a synthetic auxin or auxin transport inhibitor selected from the group consisting of synthetic auxin herbicides, wherein the synthetic auxin herbicide is selected from the group consisting of: 2,4-D, 2,4-DB; 2,3,6-TBA, cyprodinil, aminopyralid, fenthionyl, fenthionyl, clofopyralid, 2,4-dichlorprop, 2,4-dichlorprop-P, dicamba, clofopyralid, fluazifop, clofopyralid, clofopyralid-MHE, clofopyralid, indolepyralid, 2-methyl-4-chloropropionic acid, P-2-methyl-4-chloropropionic acid, MCPA, MCPA-thioethyl, MCPB, piclopram, quinclorac, clomeclorac, triclopyr, agriculturally acceptable salts and esters thereof, and combinations thereof.
32. The composition according to claim 25 or 27, wherein The second herbicide is glyphosate or an agriculturally acceptable salt or ester thereof.
33. The composition according to claim 25 or 27, wherein The second herbicide is glufosinate-ammonium or an agriculturally acceptable salt or ester thereof.
34. The composition according to claim 25 or 27, wherein The second herbicide is selected from the group consisting of bromoxynil, fluazifop, fluazifop, fluazifop, isoxafoetida, triazolam, cypermethrin, quinpyraclostrobin, and fluazifop-butyl.
35. The composition of claims 25-34 further comprising a safener.
36. The composition according to claim 35, wherein The safener is an azole safener.
37. The composition according to claim 36, wherein The safener is selected from the group consisting of: fenthiocarb, fenthiocarb, oxadiazole, isoxadiazole, pyraclostrobin, agriculturally acceptable salts or esters thereof, or combinations thereof. In some aspects, the carboxylic acid azole safener may include fenthiocarb ethyl, isoxadiazole ethyl and pyraclostrobin diethyl.
38. A composition according to any one of the preceding claims, wherein The concentration of the active ingredient in the composition is 0.001 to 98 weight percent.
39. A method of controlling undesirable vegetation, the method comprising contacting the vegetation or the locus thereof with a herbicidally effective amount of a compound according to any one of claims or applying to the soil a herbicidally effective amount of a compound according to any one of claims to prevent emergence of vegetation.
40. The method of controlling undesirable vegetation of claim 39, wherein: The compounds are applied at an application rate of between about 200 grams to about 2,000 grams acid equivalent per hectare (g ae / ha).
41. A method of controlling undesirable vegetation according to claim 40, wherein: The application rate is between about 800 g ae / ha and about 1,200 g ae / ha.
42. A method of controlling undesirable vegetation in a crop that has become tolerant or resistant to 2,4-dichlorophenoxyacetic acid, the method comprising contacting the vegetation or the locus thereof with a herbicidally effective amount of a compound according to any one of the preceding claims or applying to the soil a herbicidally effective amount of a compound according to any one of the preceding claims to prevent emergence of vegetation.
Citation Information
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