A [1,2,4]oxadiazole pyridine compound and its application

Abstract

The present invention provides a [1,2,4]oxadiazole pyridine compound of Formula I, which exhibits excellent herbicidal activity, excellent selectivity between crops and weeds, and high safety for crops. Formula I has the following general structure: #imgabs0# wherein X, Y, R1, R2, and R3 have the same meanings as described herein. The present invention also discloses a method for preparing the compound of Formula I and a herbicidal composition containing the compound of Formula I.

Description

Technical Field

[0001] The present invention relates to the field of agriculture. Specifically, the present invention provides a new [1,2,4] oxadiazole pyridine compound and a preparation method thereof, and application of a composition containing these compounds in agriculture. Background Art

[0002] Hormone herbicides, as the first type of organic selective herbicides, are one of the most widely used herbicides in the world. They include 2,4-D, 2-Methyl-4-chloro-2, dicamba, quinclorac, flupyralid, etc. With the continuous development of this type of herbicide, hormone-type herbicides with aryl picolinate structures have also been developed, such as flupyralid. and clopidogrel

[0003] Chinese patent (CN114478506A) discloses a class of pyridine oxazole compounds having the following general structure: Under relatively similar conditions, the compound of Example 1 exhibited better herbicidal activity. In terms of crop safety, the compounds of Examples 5 and 9 exhibited better safety activity.

[0004] Developing more excellent herbicides is the research and development goal of those skilled in the art. During the research and development process, the applicant developed oxadiazole pyridine compounds, and obtained compounds with better weed control effects and good commercial prospects. Summary of the Invention

[0005] The present invention provides a [1,2,4]oxadiazole pyridine compound represented by formula I and stereoisomers, nitrogen oxides and agriculturally acceptable salts thereof. The compounds of the present invention have excellent herbicidal activity and excellent selectivity between crops and weeds, and are highly safe for crops.

[0006] The present invention generally provides a compound represented by formula I,

[0007] in,

[0008] X is selected from optionally substituted alkyl, optionally substituted alkoxy, optionally substituted amino, halogen, cyano, nitro; n is 0, 1 or 2;

[0009] Y is selected from halogen, optionally substituted alkyl, optionally substituted alkoxy, optionally substituted alkylthio, optionally substituted amino, nitro, cyano, sulfonyl (R'-S(=O)2-", R' is one of alkyl, aryl, and heteroaryl), and m is 0, 1, 2, 3, 4, or 5;

[0010] R1 is selected from H, optionally substituted alkyl;

[0011] R2 and R3 are independently selected from H, optionally substituted alkyl, optionally substituted acyl (ZC(=O)2-, Z is alkyl or aryl), or a nitrogen-containing optionally substituted heterocyclic group composed of R2 and R3 together with N atom; including stereoisomers, nitrogen oxides and agriculturally acceptable salts thereof.

[0012] The present invention also provides a method for preparing a compound of formula I, which comprises preparing the compound of formula II with an N-hydroxyamidine compound, and the reverse synthesis route is as follows:

[0013]

[0014] wherein X, Y, R1, R2, R3, m and n are as defined above, and R is an optionally substituted alkyl group, an optionally substituted aryl group, preferably a C1-C6 alkyl group and a phenyl group, more preferably a methyl group or an ethyl group;

[0015] In another aspect, the present invention provides a composition comprising the compound of formula I of the present invention.

[0016] The present invention also provides a herbicidal composition comprising the compound of formula I of the present invention and at least one pesticide-acceptable adjuvant.

[0017] In another aspect, the present invention provides use of the compound of the present invention or a composition comprising the compound of the present invention in agriculture.

[0018] The invention also provides a method for controlling undesirable weeds in useful plants.

[0019] Beneficial effects of the present invention

[0020] The compound of the present invention has more efficient herbicidal activity and is safe for crops, and has broad application prospects. DETAILED DESCRIPTION

[0021] In order to make the purpose, technical solutions and advantages of the embodiments of the present invention clearer, the technical solutions in the embodiments of the present invention will be clearly and completely described below. Obviously, the described embodiments are part of the embodiments of the present invention, not all of the embodiments. Based on the embodiments of the present invention, all other embodiments obtained by ordinary technicians in this field without making creative work are within the scope of protection of the present invention. Unless otherwise expressly stated, throughout the specification and claims, the term "including" or its variations such as "comprising" or "including" will be understood to include the stated components or steps, without excluding other material components or steps.

[0022] Furthermore, in order to better illustrate the present invention, numerous specific details are given in the following detailed description.

[0023] Those skilled in the art will appreciate that the present invention can be practiced without certain specific details. In some embodiments, raw materials, methods, means, etc. well known to those skilled in the art are not described in detail in order to highlight the main purpose of the present invention.

[0024] As used herein, the terms "control" and "extermination" are synonyms.

[0025] As used herein, the terms "unwanted vegetation" and "harmful plants" and "weeds" are synonymous and refer to any undesirable plants, including not only important agricultural weeds but also volunteer crop plants.

[0026] As used herein, "weed control" or "herbicide" means a compound that controls or modifies plant growth. The term "effective amount" means the amount of a compound or a combination of compounds that produces an effect that controls or modifies plant growth. Controlled or modified effects include all deviations from natural development, such as killing, delaying, leaf burn, albinism, dwarfing, and the like. The term "plant" refers to all visible parts of a plant, including seeds, seedlings, young plants, roots, tubers, stems, stalks, leaves, and fruits. "Useful plants" according to the present invention include, but are not limited to, perennial crops such as citrus fruits, grapevines, nuts, oil palm, olives, pome fruits, drupes, and rubber, as well as annual arable crops such as barley, wheat, cotton, rapeseed, corn, rice, soybeans, sugar beets, sugar cane, sunflowers, ornamentals, switchgrass, turf, and vegetables, especially rice, corn, and soybeans.

[0027] If the compounds of formula I described herein are capable of forming geometrical isomers, such as E / Z isomers, both the pure isomers and mixtures thereof can be used in the compositions according to the invention.

[0028] If the compounds of formula I described herein have one or more chiral centers and therefore exist as enantiomers or diastereomers, the pure enantiomers, racemates, or diastereomers can be used in the compositions of the present invention.

[0029] If the compounds of the formula I according to the invention have functional groups which can be ionized, they can also be used in the form of their agriculturally acceptable salts or mixtures thereof.

[0030] Preferred cations are ions of alkali metals, preferably lithium, sodium and potassium, ions of alkaline earth metals, preferably calcium and magnesium, and ions of transition metals, preferably manganese, copper, zinc and iron.

[0031] Anions useful for acid addition salts are primarily chloride, bromide, fluoride, iodide, hydrogen sulfate, sulfate, dihydrogen phosphate, hydrogen phosphate, nitrate, hydrogen carbonate, and carbonate.

[0032] The term halogen in the definitions of the variables according to the invention denotes in each case fluorine, chlorine, bromine and iodine.

[0033] In the present invention, "sulfonyl" refers to a group containing "R'-S(=O)2-", where R' is an alkyl group, an aryl group, or a heteroaryl group, for example, an alkylsulfonyl group or an arylsulfonyl group. The alkylsulfonyl group is preferably a C1-C6 alkylsulfonyl group, and particularly preferably a methylsulfonyl group, an ethylsulfonyl group, or a propylsulfonyl group, but is not limited thereto.

[0034] In the present invention, "acyl" refers to a group containing "ZC(=O)-", where Z is an alkyl group or an aryl group, for example, preferably a C1-C6 alkyl acyl group, particularly preferably a formyl group, an acetyl group, a substituted aryl acyl group, and a benzoyl group, but not limited thereto.

[0035] It should be noted that, unless otherwise expressly stated, the description methods used in the present invention, "each...independently is" and "···each independently is" and "···independently is" can be interchanged and should be understood in a broad sense. It can mean that in different groups, the specific options expressed by the same symbols do not affect each other, or it can mean that in the same group, the specific options expressed by the same symbols do not affect each other.

[0036] All hydrocarbon chains, i.e., all alkyl groups, in the present invention may be straight or branched. n ~C m The subscripts in each case indicate the number of carbon atoms in the group. The term "alkyl" as used herein (and in other groups containing alkyl, such as the alkyl moiety of an alkoxy group) includes, for example, methyl, ethyl, n-propyl, isopropyl, n-butyl, 1-methylpropyl (sec-butyl), 2-methylpropyl (isobutyl), 1,1-dimethylethyl (tert-butyl), n-pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, hexyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl-1-methylpropyl or 1-ethyl-2-methylpropyl.

[0037] Alkylthio, without special restrictions, generally refers to "alkyl-S-", for example, C1-C 10 Alkylthio, preferably C1-C6 alkylthio, more preferably CH3S-, C2H5S-, C3H7S-, C4H9S-, C5H11 S-, C6H 13 S- etc., but not limited to.

[0038] Alkoxy, not specifically limited, generally refers to "alkyl-O-", for example, C1-C 10 Alkoxy, preferably C1-C6 alkoxy, more preferably methoxy, ethoxy, propoxy, etc., but not limited thereto.

[0039] The term "optionally substituted" means that the relevant group may be substituted by a substituent or may not be substituted.

[0040] When a related group (such as an alkyl group) is substituted with a substituent, the substituent may include a hydroxyl group, a cyano group, a nitro group, a halogen group, an alkyl group, an alkoxy group, or an alkylthio group. When an alkyl group is substituted with a halogen group, a haloalkyl group is formed, and a haloalkyl group may be a group in which some or all of the hydrogen atoms on the alkyl group are substituted with a halogen group, such as, for example, a fluoromethyl group, a difluoromethyl group, or a trifluoromethyl group, but is not limited thereto. An alkyl group may be substituted with an alkoxy group, such as, for example, a C1-C6 alkoxy-C1-C6 alkyl group, but is not limited thereto. An optionally substituted amino group refers to a group in which the H on the amino group may be substituted with an optional substituent group, preferably monosubstituted or disubstituted with a C1-C6 alkyl group, such as, for example, a methylamino group, an ethylamino group, a dimethylamino group, or a diethyl group, but is not limited thereto. An alkyl group may also be substituted with an alkylthio group, such as, for example, a C1-C6 alkylthio-C1-C6 alkyl group, but is not limited thereto.

[0041] The term "ring" or "cycloalkyl" herein refers to a monocyclic or bicyclic alicyclic radical generally having 3 to 6 carbon atoms ("C3-C6 cycloalkyl"). Examples of monocyclic radicals having 3 to 6 carbon atoms include cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl.

[0042] Heterocyclyl: a monocyclic or bicyclic saturated, partially unsaturated or aromatic heterocycle having 3 or more, for example 3 to 10 ring atoms, for example, a 3-, 4-, 5-, 6- or 7-membered heterocycle containing 1 to 4 identical or different heteroatoms selected from oxygen, sulfur and nitrogen, for example: azetidinyl, oxetanyl, thietanyl, pyrrolidinyl (e.g. 2-pyrrolidinyl), 2-pyrrolinyl, 3-pyrrolinyl, pyrazolidinyl, imidazolinyl, imidazolidinyl, tetrahydrofuranyl, dihydrofuranyl, tetrahydrothiophenyl, dihydrothiophenyl, 1,3-dioxolane, dithiolanyl, tetrahydropyranyl, dihydropyranyl , 2H-pyranyl, 4H-pyranyl, tetrahydrothiopyranyl, piperidinyl (2-piperidinyl, 3-piperidinyl, 4-piperidinyl, morpholinyl, thiomorpholinyl, (1-oxo)-thiomorpholinyl, (1,1-dioxo)-thiomorpholinyl, piperazinyl, homopiperazinyl, homopiperidinyl, 2-oxa-5-azabicyclo[2.2.1]hept-5-yl, tetrahydropyridinyl. Examples of heterocyclic groups in which the -CH2- group is replaced by -C(=O)- include, but are not limited to, 2-oxopyrrolidinyl, oxo-1,3-thiazolidinyl, 2-piperidonyl, 3,5-dioxopiperidinyl.

[0043] The present invention generally provides a compound represented by formula I,

[0044] in,

[0045] X is selected from optionally substituted alkyl, optionally substituted alkoxy, optionally substituted amino, halogen, cyano, nitro, and n is 0, 1 or 2;

[0046] Y is selected from halogen, optionally substituted alkyl, optionally substituted alkoxy, optionally substituted alkylthio, optionally substituted amino, nitro, cyano, sulfonyl (R'-S(=O)2-, R' is one of optionally substituted alkyl, optionally substituted aryl, and optionally substituted heteroaryl), m is 0, 1, 2, 3, 4 or 5;

[0047] R1 is selected from H, optionally substituted alkyl;

[0048] R2 and R3 are independently selected from H, optionally substituted alkyl, optionally substituted acyl (ZC(=O)2-, Z is an optionally substituted alkyl or aryl), or a nitrogen-containing optionally substituted heterocyclic group composed of R2 and R3 together with N atom; and their stereoisomers, nitrogen oxides and agriculturally acceptable salts.

[0049] The following statements regarding the variables of the compounds of the formula I and preferred embodiments of the variables, features of the uses and methods according to the invention and features of the compositions according to the invention are valid both on their own and preferably in combination with one another.

[0050] In some preferred embodiments, X is selected from one or more of halogen (preferably -F, -Cl, -Br, -I), C1-C6 alkyl substituted by halogen (preferably -CF3, -CHF2), cyano, nitro and C1-C6 alkyl, and n is 0, 1 or 2; more preferably, one or more of -F, -Cl, -Br, -I, -CF3, -CHF2, -NO2, -CN, C1-C3 alkyl, and n is 0, 1 or 2.

[0051] In some embodiments, Y is selected from one or more of halogen, C1-C6 alkyl, C1-C6 alkoxy, halogenated C1-C6 alkyl, C1-C6 alkylthio, amino monosubstituted or disubstituted by C1-C6 alkyl, C1-C6 alkoxy-C1-C6 alkyl, C1-C6 alkylthio-C1-C6 alkyl, nitro, cyano and C1-C6 alkyl-S(=O)2-, and m is 0, 1, 2, 3, 4 or 5. Preferred are one or more of -H, -F, -Cl, -Br, -I, C1-C4 alkyl, C1-C4 alkoxy, nitro, cyano, C1-C4 alkyl-SO2-, and halogenated C1-C3 alkyl; particularly preferred are one or more of -F, -Cl, -Br, -I, -CH3, -CH2CH3, -CH2CH2CH3, -CH(CH3)2, -OCH3, -OCH2CH3, -OCH2 CH2CH3, -OCH(CH3)2, -CF3, -CHF2, -NO2, -CN, -SO2CH3, -SO2 CH2CH3, -SO2CH2CH2CH3, and -SO2CH(CH3)2.

[0052] In some embodiments, R1 is selected from H, optionally substituted alkyl, particularly preferably H, -CH3, -CH2CH3, -CH2CH2CH3, -CH(CH3)2.

[0053] In some embodiments, R2 and R3 are independently selected from one or more of H, C1-C6 alkyl, C1-C6 alkyl-C(=O)-, or R2 and R3 together with N atom form a nitrogen-containing 3-10 membered heterocyclic group; preferably H, C1-C4 alkyl, C1-C4 alkyl-C(=O)-, R2, R3 and N atom form a nitrogen-containing 3-10 membered heterocyclic ring or more; particularly preferably H, -CH3, -CH2CH3, -CH2CH2CH3, -CH(CH3)2, -COCH3, -CO CH2CH3, -CO CH2CH2CH3, -CO CH(CH3)2, One or more of.

[0054] The preferred compound of formula I of the present invention is a compound of formula II:

[0055] in,

[0056] R1 is H, optionally substituted alkyl; preferably H, C1-C6 alkyl, C1-C6 alkoxy-C1-C6 alkyl, C1-C6 alkylthio-C1-C6 alkyl; more preferably H or C1-C6 alkyl; most preferably H or C1-C4 alkyl; particularly preferably H, -CH3, -CH2CH3, -CH2CH2CH3, -CH(CH3)2;

[0057] R2 and R3 are independently selected from one of H, C1-C6 alkyl, and C1-C6 alkyl-C(=O)-, preferably one of H, C1-C4 alkyl, and C1-C4 alkyl-C(=O)-; particularly preferably one of H, -CH3, -CH2CH3, -CH2CH2CH3, -CH(CH3)2, -COCH3 (acetyl), -COCH2CH3 (propionyl), -COCH2CH2CH3 (butyryl), and -COCH(CH3)2 (tert-butyryl);

[0058] Or R2, R3 and N atom form a nitrogen-containing 3-10 membered heterocyclic ring, preferably

[0059] X1 and X2 are independently selected from one of H, halogen, nitro, cyano, and halogenated C1-C6 alkyl, preferably one of H, F, Cl, Br, I, nitro, cyano, and halogenated C1-C3 alkyl; particularly preferably one of -F, -Cl, -Br, -I, -CF3, -CHF2, -NO2, and -CN;

[0060] Y1, Y2, Y3, Y4 and Y5 are independently selected from H, halogen, C1-C6 alkyl, C1-C6 alkoxy, halogenated C1-C6 alkyl, C1-C6 alkyl-SO2-, nitro, cyano, preferably H, F, Cl, Br, I, C1-C4 alkyl, C1-C4 alkoxy, nitro, cyano, C1-C4 alkyl-SO2-, halogenated C1-C3 alkyl; particularly preferably -F, -Cl, -Br, -I, -CH3, -CH2CH3, -CH2CH2CH3, -CH(CH3)2, -OCH3, -OCH2CH3, -OCH2CH2CH3, -OCH(CH3)2, -CF3, -CHF2, -NO2, -CN, -SO2CH3, -SO2CH2CH3, -SO2CH2CH2CH3, -SO2CH(CH3)2; and its stereoisomers, nitrogen oxides and agriculturally acceptable salts thereof.

[0061] The present invention particularly prefers the following compounds:

[0062] The present invention also provides a method for preparing the compound of formula I, and the synthetic route thereof is as follows:

[0063]

[0064] wherein X, Y, R1, R2, R3, m and n are as defined above, and R is an optionally substituted alkyl group or an optionally substituted aryl group, preferably a C1-C6 alkyl group, more preferably a methyl group or an ethyl group.

[0065] Formula II is synthesized with reference to CN01806323.3 (application date January 12, 2001, authorization announcement number CN1281591C), CN02814816.9 (application date July 30, 2022, authorization announcement number CN1245401C) and methods known in the art; among them, CN01806323.3 introduces the synthesis of 4-aminopicolinate in detail, and CN02814816.9 introduces the method of synthesizing Formula II from aromatic or heteroaromatic groups and substituted pyridine carboxylates.

[0066] The above synthesis steps include reacting an N-hydroxyamidine compound and a compound of formula II in an organic solvent to prepare a compound of formula I. The solvent is preferably tetrahydrofuran, petroleum ether, benzene, toluene, or dioxane.

[0067] In the above synthesis, a base is preferably added during the reaction, and the base is one of sodium hydride, sodium methoxide, and sodium ethoxide.

[0068] The preferred reaction steps include dissolving the N-hydroxyamidine compound in an organic solvent, adding a base at 20-100°C, stirring for 0.5-2h, adding a solution of formula II, reacting at 20-100°C for 1-5h, and post-processing to obtain the target product.

[0069] The present invention provides a composition comprising the compound of the present invention or a stereoisomer, nitrogen oxide or salt thereof of the compound of the present invention.

[0070] The compound of formula (I) can be prepared into conventional formulations by conventional formulation methods, and the form of use depends on the specific purpose of use. The formulations are prepared using conventional known methods, for example, by mixing the active compound with a solvent and / or a carrier, and if necessary, adding suitable emulsifiers and dispersants or other commonly used adjuvants.

[0071] Typically, the compounds of the present invention are mixed with suitable adjuvants, for example, inert carriers such as solid carriers, liquid carriers or gaseous carriers to prepare the agents for preventing and controlling harmful plants of the present invention, and, if necessary, surfactants and other formulation adjuvants are added to make liquid compositions including solutions (including emulsifiable concentrates), suspensions, emulsions (including microemulsions and / or suspoemulsions), etc., which can optionally be thickened into gels. The general types of aqueous liquid compositions are soluble concentrates, suspension concentrates, capsule suspensions, concentrated emulsions, microemulsions and suspoemulsions. The general types of non-aqueous liquid compositions are emulsifiable concentrates, microemulsifiable concentrates, dispersible concentrates and oil dispersions. The compositions of the present invention can also be made into suitable solid formulations as needed, for example, dusts, powders, granules, pellets, pellets, lozenges, tablets, filled films (including seed coatings), etc., which can be water-dispersible ("wettable") or water-soluble. Films and coatings formed by film-forming solutions or flowable suspensions are particularly useful for seed treatment. The active ingredient can be (micro)encapsulated and further formed into a suspension or solid formulation; or the entire active ingredient formulation can be encapsulated (or "coated"). Encapsulation can control or delay the release of the active ingredient. Emulsifiable granules combine the advantages of both emulsifiable concentrates and dry granules. High-concentration compositions are mainly used as intermediates for other formulations.

[0072] Examples of commonly used solid carriers include: fine powder or granules of clay (e.g., kaolin clay, diatomaceous earth, bentonite), synthetic hydrous silica, talc, ceramics, other inorganic materials (e.g., quartz, sulfur, activated carbon, calcium carbonate or hydrated silica), chemical fertilizers (e.g., ammonium sulfate, ammonium phosphate, ammonium nitrate, urea or ammonium chloride) and synthetic resins (e.g., polyester resins such as polypropylene, polyacrylonitrile, polymethyl methacrylate and polyethylene terephthalate, nylon resins, polyamide resins, polyvinyl chloride, polyvinylidene chloride, vinyl chloride-propylene copolymers), etc.

[0073] Examples of commonly used liquid carriers include: water, alcohols (e.g., methanol, ethanol, isopropanol, butanol, hexanol, benzyl alcohol, ethylene glycol, propylene glycol or phenoxyethanol), ketones (e.g., acetone, methyl ethyl ketone or cyclohexanone), aromatic hydrocarbons (e.g., toluene, xylene, ethylbenzene, dodecylbenzene, phenylxylylethane or methylnaphthalene); aliphatic hydrocarbons (e.g., hexane, cyclohexane, kerosene or light oil), esters (e.g., ethyl acetate, butyl acetate, isopropyl myristate, ethyl oleate, diisopropyl adipate, diisobutyl adipate or propylene glycol); propylene glycol monomethyl ether acetate, propylene carbonate), nitriles (e.g. acetonitrile or isobutyronitrile), ethers (e.g. diisopropyl ether, 1,4-dioxane, ethylene glycol dimethyl ether, diethylene glycol dimethyl ether, diethylene glycol monomethyl ether, propylene glycol monomethyl ether, dipropylene glycol monomethyl ether or 3-methoxy-3-methyl-1-butanol), amides (e.g. N,N-dimethylformamide or N,N-dimethylacetamide), halogenated hydrocarbons (e.g. dichloromethane, trichloroethane or carbon tetrachloride), sulfoxides (e.g. dimethyl sulfoxide) and vegetable oils (e.g. soybean oil or cottonseed oil).

[0074] The auxiliary agent used in the present invention includes a commonly used surfactant, and the surfactant includes: a nonionic surfactant, an anionic surfactant or a cationic surfactant.

[0075] Conventional nonionic surfactants to which the present invention can be applied include, but are not limited to, alcohol alkoxylates, such as those based on natural and synthetic alcohols (which are branched or linear) and prepared from alcohols and ethylene oxide, propylene oxide, butylene oxide, or mixtures thereof; amine ethoxylations, alkanolamides, and ethoxylated alkanolamides; alkoxylated triglycerides, such as ethoxylated soybean, castor, and rapeseed oils; alkylphenol alkoxylates, such as octylphenol ethoxylates, nonylphenol ethoxylates, dinonylphenol ethoxylates, and dodecylphenol ethoxylates (prepared from phenol and ethylene oxide, propylene oxide, butylene oxide, or mixtures thereof); block polymers prepared from ethylene oxide or propylene oxide and reverse block polymers, wherein the terminal blocks are prepared from propylene oxide; ethoxylated propylene oxides; ethoxylated fatty acids; ethoxylated fatty esters and oils; ethoxylated methyl esters; ethoxylated tristyrylphenols (including those prepared from ethylene oxide, propylene oxide, butylene oxide, or mixtures thereof); fatty acid esters, glycerides, lanolin-based derivatives, polyethoxylated esters, such as polyethoxylated sorbitan fatty acid esters, polyethoxylated sorbitan fatty acid esters, and polyethoxylated glycerol fatty acid esters; other sorbitan derivatives, such as sorbitan esters; polymeric surfactants such as random copolymers, block copolymers, alkyd PEG (polyethylene glycol) resins, graft or comb polymers, and star polymers; polyethylene glycol (PEG); polyethylene glycol fatty acid esters; silicone-based surfactants; and sugar derivatives such as sucrose esters, alkyl polyglucosides, and alkyl polysaccharides.

[0076] Anionic surfactants that can be used in the preparation of the formulation of the compounds of the present invention include, but are not limited to, alkylaryl sulfonic acids and their salts; carboxylated alcohol or alkylphenol ethoxylates; diphenylsulfonate derivatives; lignin and lignin derivatives, such as lignin sulfonates; maleic acid or succinic acid or their anhydrides; olefin sulfonates; phosphates, such as phosphates of alcohol alkoxylates, phosphates of alkylphenol alkoxylates and phosphates of styrylphenol ethoxylates; protein-based surfactants; sarcosine derivatives; styrylphenol ether sulfates; sulfates and sulfonates of oils and fatty acids; sulfates and sulfonates of ethoxylated alkylphenols; sulfates of alcohols; sulfates of ethoxylated alcohols; sulfonates of amines and amides, such as N,N-alkyltaurates; sulfonates of benzene, isopropyl benzene, toluene, xylene, and dodecylbenzene and tridecylbenzene; sulfonates of condensed naphthalene; sulfonates of naphthalene and alkylnaphthalene; sulfonates of petroleum fractions; sulfosuccinamates; and sulfosuccinates and their derivatives, such as dialkylsulfosuccinates.

[0077] Conventional cationic surfactants that can be used in the preparation of formulations of the compounds of the present invention include, but are not limited to, amides and ethoxylated amides; amines, such as N-alkylpropylenediamine, tripropylenetriamine and dipropylenetetramine, as well as ethoxylated amines, ethoxylated diamines and propoxylated amines (prepared from amines and ethylene oxide, propylene oxide, butylene oxide or mixtures thereof); amine salts, such as amine acetates and diamine salts; quaternary ammonium salts, such as quaternary ammonium salts, ethoxylated quaternary ammonium salts and diquaternary ammonium salts; and amine oxides, such as alkyldimethylamine oxide and di-(2-hydroxyethyl)-alkylamine oxide.

[0078] During the preparation of the compound of the present invention, other suitable formulation adjuvants may be added as needed, including, for example, adhesives, dispersants, antifreeze agents, colorants, and stabilizers. Specific examples include starch, gum arabic, cellulose derivatives and alginic acid, lignin derivatives, bentonite, polyvinyl alcohol, polyvinyl pyrrolidone and polyacrylic acid, a mixture of 2,6-di-tert-butyl-4-methylphenol, 2-tert-butyl-4-methoxyphenol, and 3-tert-butyl-4-methoxyphenol, propylene glycol, glycerol, and the like.

[0079] The pesticide agent for controlling undesirable plants of the present invention can be used in farmlands of the following crops. The crops include: corn, rice, wheat, barley, rye, oats, sorghum, cotton, soybeans, peanuts, buckwheat, beets, rapeseed, sunflowers, sugarcane, tobacco, eggplant, tomatoes, bell peppers, peppers, potatoes, cucumbers, pumpkins, zucchini, watermelons, melons, Japanese radish, white radish, horseradish, kohlrabi, cabbage, cabbage, mustard greens, broccoli, cauliflower, garland chrysanthemum, artichokes, lettuce, scallions, onions, garlic or asparagus, carrots, parsley, celery, parsnips, spinach, Swiss chard, apples, pears, papaya, peaches, plums, nectarines, plums, cherries, apricots, prunes, Wenzhou mandarin oranges, oranges, lemons, limes, grapefruits, chestnuts, walnuts, hazelnuts, almonds, pistachios, cashews or macadamia nuts, grapes, persimmons, olives, loquats, bananas, coffee, dates, coconut palms, oil palms, etc.

[0080] The compound of the present invention has better safety to farmland crops than the compounds disclosed in the prior art, especially to corn, wheat, rice, soybean, rape and the like.

[0081] The compounds of general formula I of the present invention have excellent herbicidal activity and crop safety. The compounds of general formula I of the present invention are suitable for plant protection and control of unwanted plants in agriculture, forestry and horticulture.

[0082] The compounds of formula I of the present invention can be used to control weeds by using an effective weed control amount of the compounds of formula I of the present invention.

[0083] The herbicidal composition or formulation of the present invention generally contains 0.1 to 95% by weight, preferably 0.5 to 90% by weight, of a compound of formula (I). When an agent containing the compound of the present invention is used to control unwanted plants and weeds, the application rate of the compound of formula I of the present invention is generally selected to be 0.01 to 1000 g per hectare, and the preferred effective amount is 0.01 to 500 g per hectare. The effective amount of the present invention refers to the application rate of the compound of formula I of the present invention. Preferred compounds of formula I of the present invention, for example, compounds 1-8, as active ingredients, have a good weed-killing effect at a dosage of 0.1 g / mu (i.e., an amount of 0.1 g of active ingredient per mu), and particularly preferred compounds have a good weed-killing effect at a dosage of 0.05 g / mu (i.e., an amount of 0.05 g of active ingredient per mu). When the pesticide composition containing the compound of formula I is used for weed control in the form of an emulsifiable concentrate, wettable powder or microemulsion, it is usually applied by diluting the formulation containing the compound of formula I of the present invention with water to a concentration of the active ingredient in the range of 0.01 to 5000 ppm. Granules or powders can be applied undiluted. Research results show that the compound of formula (I) of the present invention has a killing effect of at least 90% on certain weeds and resistant weeds in a concentration range of 0.01 to 100 ppm (0.01 mg / L to 100 mg / L). Preferred compounds have a killing effect of at least 90% on certain weeds and resistant weeds in a range of 0.1 ppm to 100 ppm.

[0084] Weeds that can be controlled by the compounds of the present invention include broadleaf weeds, such as Artemisia selengensis, Shepherd's purse, Duck tongue grass, Gallia, Zelacquer, Velvet, Wheat family, Xanthium, Wheat bottle grass, Chenopodium album, Thistle (cardilla), Cirsium, Polygonum multiflorum, Chickweed, Vaccaria, Polygonum truncatum, Herba Lycopodii, Wild Geranium, Mud Cabbage, Tongquan Grass, Vetch, Alternanthera philadelphica, Amaranthus, Solanum nigrum, Lantern grass, Purslane, Amaranth, Amaranthus retroflexus, Cyperus rotundus, Humulus, Sagittaria etc.; also include Poaceae weeds, such as Alopecurus mume, Digitaria, Wild Oats, Bluegrass, Echinochloa crus-galli, Achnatherum splendens, Sestrife grandis, Setaria officinalis, Teff, Coleus chinensis, Hard grass, Bromus, Goosegrass, Bermuda grass, Leptochloa chinensis etc.; also include Cyperus weeds, such as Cyperus rotundus, Cyperus difformis, Cyperus watergrass, Cyperus angustifolia, Cyperus rotundus etc., but are not limited to these.

[0085] The undesirable plants described in the present invention are further preferably Echinochloa crus-galli, Leptochloa chinensis, Dalbergia vaginalis, Alternanthera philoxeroides, Cyperus difformis and Polygonum syringae.

[0086] The compounds of formula I of the present invention exhibit high safety on important crops, including but not limited to barley, cotton, wheat, rapeseed, sugar beet, corn (maize), sorghum, soybean, rice, oats, peanuts, vegetables, tomatoes, and potatoes.

[0087] Preparation Example

[0088] In this specification, if there is any difference between the chemical name and the chemical structure, the structure is preferred. Generally, the compounds of the present invention can be prepared by the methods described herein, unless otherwise specified. The raw materials, reagents, etc. used to prepare the compounds of the present invention are all commercially available or can be prepared by methods conventional in the art.

[0089] Example 1 Preparation of 4-amino-3-chloro-6-(2,4-dichloro-3-methoxyphenyl)-2-[1,2,4]oxadiazol-5-ylpyridine (Compound 1)

[0090]

[0091] Take 1.2g of N-hydroxyformamidine and dissolve it in tetrahydrofuran. Add 0.8g of sodium hydride at 30°C, stir for 1h, then add 4-amino-3-chloro-6-(2,4-dichloro-3-methoxyphenyl)-pyridine-2-carboxylic acid methyl ester (7.2g) in tetrahydrofuran, and react at 30°C for 4h. After the reaction, add a large amount of ice water to quench the sodium hydride, add dichloroethane for extraction, and concentrate the organic layer to obtain 6.7g of the target product with a yield of 90%.

[0092] 1H NMR (300MHz, CDCl3) δ7.22-7.38(m,2H), δ7.14(s,1H), δ5.4(s,1H), δ4.98(s,2H), δ3.79(s,3H)

[0093] Example 2 Preparation of 4-amino-3-cyano-2-(4-methylsulfonylphenyl)-6-(3-methyl-[1,2,4]oxadiazol-5-yl)-pyridine (Compound 2)

[0094]

[0095] 3.0 g of N-hydroxyacetamidine was dissolved in tetrahydrofuran, 1.0 g of sodium hydride was added at 50 ° C, and the mixture was stirred for 0.5 h. Then, a solution of 4-amino-5-cyano-6-(4-methylsulfonylphenyl)-pyridine-2-carboxylic acid methyl ester (6.6 g) in tetrahydrofuran was added and the mixture was reacted at 60 ° C for 2 h. After the reaction was completed, the temperature was lowered, a large amount of ice water was added to quench the sodium hydride, and dichloroethane was added for extraction. The organic layer was concentrated to obtain 6.8 g of the target product with a yield of 96%.

[0096] 1H NMR (300MHz, CDCl3): δ8.02-8.14 (d, 2H), δ7.89-7.96 (d, 2H), δ6.93 (s, 1H), δ4.89 (s, 2H), δ2.87 (s, 3H), δ2.58 (s, 3H)

[0097] Example 3 Preparation of 4-amino-3-chloro-6-(4-chlorophenyl)-5-fluoro-2-(3-methyl-[1,2,4]oxadiazol-5-yl)-pyridine (Compound 3)

[0098]

[0099] Take 2.8g of N-hydroxyacetamidine, dissolve it in dioxane, add 1.0g of sodium hydride at 50°C, stir for 1.5h, add 4-amino-3-chloro-6-(4-chlorophenyl)-5-fluoropyridine-2-carboxylic acid methyl ester (6.3g) in dioxane, react at 100°C for 1h, cool after the reaction, add a large amount of ice water to quench the sodium hydride, add dichloroethane for extraction, and concentrate the organic layer to obtain 6.2g of the target product with a yield of 92%.

[0100] 1H NMR (300MHz, CDCl3): δ7.92-7.94(d,2H), δ7.43-7.48(d,2H),

[0101] δ5.04(s,2H),δ2.54(s,3H)

[0102] Example 4 Preparation of 4-amino-3-chloro-2-(3-isopropyl-[1,2,4]oxadiazol-5-yl)-6-p-tolyl-5-trifluoromethylpyridine (Compound 4)

[0103]

[0104] Take 3.3g of N-hydroxy-isobutylamidine, dissolve it in toluene, add 1.4g of sodium hydride at 80°C, stir for 0.8h, add 4-amino-3-chloro-6-p-tolyl-5-trifluoromethylpyridine-2-carboxylic acid ethyl ester (7.2g) in toluene, react at 60°C for 2h, cool after the reaction, add a large amount of ice water to quench the sodium hydride, and concentrate the organic layer to obtain 7.5g of the target product with a yield of 94%.

[0105] 1H NMR (300MHz, CDCl3): δ7.82-7.89(d,2H), δ7.23-7.38(d,2H),

[0106] δ5.01(s,2H), δ3.01-3.24(m,1H), δ2.44(s,3H), 1.32-1.39(d,6H)

[0107] Example 5 Preparation of 4-methylamino-2-(3-ethyl-[1,2,4]oxadiazol-5-yl)-3-nitro-6-phenylpyridine (Compound 5)

[0108]

[0109] Take 2.8g of N-hydroxypropionamidine, dissolve it in petroleum ether, add 0.8g of sodium hydride at 20°C, stir for 2h, add 4-methylamino-3-nitro-6-phenylpyridine-2-carboxylic acid methyl ester (5.7g) in petroleum ether, react at 25°C for 5h, add a large amount of ice water after the reaction is completed to quench the sodium hydride, and take the organic layer and concentrate to obtain 5.6g of the target product with a yield of 87%.

[0110] 1H NMR (300MHz, CDCl3): δ7.88-7.96 (d, 2H), δ7.25-7.42 (m, 3H), δ7.11 (s, 1H), δ4.54 (br, 1H), δ2.29-2.54 (m, 5H), δ1.18-1.29 (t, 3H)

[0111] Example 6 Preparation of N-[2-(4-bromo-3-cyanophenyl)-5-chloro-3-fluoro-6-(3-methyl-[1,2,4]oxadiazol-5-yl)-pyridin-4-yl]-acetamide (Compound 6)

[0112]

[0113] Take 3.0g of N-hydroxyacetamidine, dissolve it in benzene, add 1.2g of sodium hydride at 70℃, stir for 0.5h, add 4-acetylamino-6-(4-bromo-3-cyanophenyl)-3-chloro-5-fluoropyridine-2-carboxylic acid methyl ester (8.5g) in benzene, react at 70℃ for 1.5h, cool after the reaction, add a large amount of ice water to quench the sodium hydride, and concentrate the organic layer to obtain 8.6g of the target product with a yield of 95%.

[0114] 1H NMR (300MHz, CDCl3): δ8.11-8.19(m,2H), δ7.69-7.81(d, 1H), 7.45(s, 1H), δ2.47(s,3H), δ2.14(s,3H)

[0115] Example 7 Preparation of 4-dimethylamino-2-(3-methyl-[1,2,4]oxadiazol-5-yl)-6-(4-nitrophenyl)-pyridine (Compound 7)

[0116]

[0117] 1.8 g of N-hydroxyacetamidine was dissolved in tetrahydrofuran, 0.6 g of sodium hydride was added at 40 ° C, and after stirring for 1 h, a solution of 4-dimethylamino-6-(4-nitrophenyl)-pyridine-2-carboxylic acid methyl ester (6.0 g) in tetrahydrofuran was added. The reaction was carried out at 60 ° C for 3 h. After the reaction was completed, the temperature was lowered and a large amount of ice water was added to quench the sodium hydride. After extraction with dichloroethane, the organic layer was concentrated to obtain 6.2 g of the target product with a yield of 96%.

[0118] 1H NMR (300MHz, CDCl3): δ8.19-8.27(m,4H), δ6.69(s, 1H), δ6.47(s, 1H), δ2.67(s,6H), δ2.53(s,3H)

[0119] Example 8 Preparation of 4-piperidinyl-5-chloro-3-fluoro-6-(2-fluoro-4-trifluoromethylphenyl)-2-(3-methyl-[1,2,4]oxadiazol-5-yl)-pyridine (Compound 8)

[0120]

[0121] Take 2.9g of N-hydroxyacetamidine and dissolve it in dioxane. Add 1.1g of sodium hydride at 60°C, stir for 0.5h, then add 4-cyclohexylamino-5-chloro-3-fluoro-6-(2-fluoro-4-trifluoromethylphenyl)-pyridine-2-carboxylic acid methyl ester (8.7g) in dioxane. React at 80°C for 1h. After the reaction is completed, cool and add a large amount of ice water to quench the sodium hydride. Add dichloroethane for extraction, and concentrate the organic layer to obtain 8.3g of the target product in a yield of 90%.

[0122] 1H NMR (300MHz, CDCl3): δ7.24-7.85 (m, 3H), δ2.81 (d, 4H), δ2.55 (s, 3H), δ1.51-1.62 (m, 6H)

[0123] Application Examples

[0124] The percentages in the preparations of the present invention are by weight. The raw materials used are either prepared by the applicant or purchased from the market.

[0125] Experimental sample: 2% active ingredient emulsifiable concentrate, the active ingredient is selected from the compounds in Examples 1-8, and the other ingredients in the emulsifiable concentrate are: 8% Nongru 8201, 2% methanol, and benzene is mixed to make up 100%.

[0126] Control sample 1: 3% clofopyralid emulsifiable concentrate (Linsco)

[0127] Control sample 2: 2% CN114478506A Example 1 compound + 8% Nongru 8201 + 2% methanol, mixed with benzene to make up 100% (refer to the CN114478506A method to synthesize a small amount of sample for experiment) (CN114478506A Example 1 compound structure is as follows: ).

[0128] Targets: Echinochloa crus-galli, Leptochloa chinensis, Dalbergia vaginalis, Alternanthera philoxeroides, Cyperus dimorphus, Polygonum syringae

[0129] Methods: Referring to NY1155.4-2006 "Guidelines for Indoor Bioassay Tests of Pesticides. Herbicides. Part 4: Activity Assays. Stem-Leaf Spray Method," air-dried soil with good permeability and a pH of 7 and an organic matter content of 2.5% was prepared and placed in a pot with a diameter of 30 cm and a height of 18 cm, with the soil filling 4 / 5 of the pot. The soil was completely moistened by infiltration irrigation from the bottom of the pot. 25-30 weed seeds were evenly sown on the soil surface and covered with soil.

[0130] The weeds were then transplanted to a greenhouse and incubated at approximately 20°C. Water was added as needed. Paddy field weeds (Echinochloa crus-galli, Dalbergia vaginalis, Cyperus dimorpha, Alternanthera philoxeroides, and Polygonum syringae) were irrigated to saturation using top irrigation, while dry field weed Leptochloa chinensis was irrigated from the bottom of the pots. After weed seedlings emerged, thinning was performed, leaving 10 weeds of uniform growth per pot evenly distributed throughout the pots. When weeds reached the 3-4 leaf stage, weeds were treated with a stem-leaf spray using a quantitative automatic sprayer (3WPSH-500E, Nanjing Agricultural Mechanization Research Institute) at a rate of 300 L / ha. Each treatment was replicated four times, with a treatment containing no active ingredient serving as a blank control. After treatment, the liquid medicine was allowed to air dry naturally and then moved into the greenhouse for conventional cultivation. The dry field weeds were watered by infiltration irrigation from the bottom of the pots, and the paddy field weeds were watered to saturation by irrigation from the top of the pots. After 14 days, the fresh weight control efficacy was observed and calculated. The results are shown in Tables 1-3.

[0131] Formula for calculating fresh weight control effect: fresh weight control effect = (fresh weight of the aboveground part of blank control weeds - fresh weight of the aboveground part of treated weeds) / fresh weight of the aboveground part of blank control weeds * 100.

[0132] Table 1 Control effect of [1,2,4] oxadiazole pyridine compounds on fresh weight of gramineous weeds Echinochloa crus-galli and Leptochloa chinensis

[0133]

[0134]

[0135] Table 2 Control efficacy of [1,2,4] oxadiazole pyridine compounds on the fresh weight of broadleaf weeds Dalbergia vaginalis, Alternanthera philoxeroides, and Polygonum syringae

[0136]

[0137]

[0138] Table 3 Control effect of [1,2,4] oxadiazole pyridine compounds on fresh weight of Cyperus dimorphus

[0139]

[0140]

[0141] Crop safety experiments

[0142] Refer to NY / T 1155.8-2007 "Guidelines for Indoor Bioassay Tests of Pesticides. Herbicides. Part 8: Crop Safety Tests. Leaf Spray Method"

[0143] Experimental sample: 2% active ingredient emulsifiable concentrate, the active ingredient is selected from the compounds in Examples 1-8, and the other ingredients in the emulsifiable concentrate are: 8% Nongru 8201, 2% methanol, and benzene is mixed to make up 100%.

[0144] Control sample 3: 2% CN114478506A Example 5 compound + 8% Nongru 8201 + 2% methanol, mixed with benzene to make up 100% (refer to the CN114478506A method to synthesize a small amount of sample for experiment) (CN114478506A Example 5 compound structure is as follows: ).

[0145] Control sample 4: 2% CN114478506A Example 9 compound + 8% Nongru 8201 + 2% methanol, mixed with benzene to make up 100% (refer to the CN114478506A method to synthesize a small amount of sample for experiment) (CN114478506A Example 9 compound structure is as follows: ).

[0146] Cultivation and Treatment of Targets: Prepare air-dried, well-permeable, sieved soil with a pH of ≈7 and an organic matter content of ≈2.5%. Fill 30 cm diameter, 18 cm height pots with soil four-fifths full. Water the soil thoroughly from the top. Soil 20–25 crop seeds are evenly sown on the soil surface, covered with ≈1.0 cm of soil, and transferred to a greenhouse for cultivation at ≈20°C. Water is replenished as appropriate. Paddy rice is top-irrigated to saturation, while dryland crops such as corn, wheat, soybean, and rapeseed are bottom-irrigated. Thinning and transplanting are performed after crop emergence. At the 3–4 leaf stage, crops are treated with a foliar spray using a quantitative automatic sprayer (3WPSH-500E, Nanjing Agricultural Mechanization Research Institute) at a rate of 300 L / ha. Four replicates are used for each treatment, and a treatment without active ingredient serves as a blank control. After treatment, the liquid was allowed to air dry naturally and then moved into the greenhouse for conventional cultivation. The dryland crops were watered by bottom infiltration irrigation of the pots, and the paddy field crops were watered to saturation by top irrigation of the pots. The results were recorded by visual inspection after 14 days. The results are shown in Table 4.

[0147] The phytotoxicity effect is expressed as follows: 0 indicates safety and no phytotoxicity; 1-10 indicates no obvious phytotoxicity; 11-30 indicates slight phytotoxicity; 31-50 indicates moderate phytotoxicity; >50 indicates severe phytotoxicity.

[0148] Table 4 Phytotoxicity of [1,2,4] oxadiazole pyridine compounds to crops

[0149]

[0150]

[0151] The compounds of the present invention have good control effects on grasses and broadleaf weeds, especially barnyard grass, Leptochloa chinensis, Dalbergia vaginalis, Alternanthera philoxeroides, Polygonum syringae, and Cyperus dimorphus. Furthermore, the compounds of the present invention are highly safe for crops, especially corn, wheat, rice, soybean, and rapeseed, showing high safety and activity. The compounds of the present invention have broad application prospects.

Claims

1. A compound represented by formula I, in, X is one or more of halogen, C1-C6 alkyl substituted by halogen, cyano and nitro; Y is selected from one or more of H, halogen, C1-C6 alkyl, C1-C6 alkoxy, halogenated C1-C6 alkyl, nitro, cyano and C1-C6 alkyl-S(=O)2-; R1 is selected from H, C1-C6 alkyl; R2 and R3 are independently selected from one or more of H, C1-C6 alkyl, C1-C6 alkyl-C(=O)-, or R2, R3 and N atom form a nitrogen-containing heterocyclic ring. One or more of the following; n is 0, 1, or 2; m is 0, 1, 2, 3, 4 or 5; and pesticidally acceptable salts thereof.

2. The compound of formula I according to claim 1, characterized in that X is selected from one or more of -F, -Cl, -Br, -I, -CF3, -CHF2, -NO2, and -CN, and n is 0, 1, or 2.

3. The compound of formula I according to claim 1, characterized in that Y is selected from one or more of H, F, Cl, Br, I, C1-C4 alkyl, C1-C4 alkoxy, nitro, cyano, C1-C4 alkyl-SO2-, and halogenated C1-C3 alkyl.

4. The compound of formula I according to claim 1, characterized in that Y is selected from one or more of -F, -Cl, -Br, -I, -CH3, -CH2CH3, -CH2CH2CH3, -CH(CH3)2, -OCH3, -OCH2CH3, -OCH2CH2CH3, -OCH(CH3)2, -CF3, -CHF2, -NO2, -CN, -SO2CH3, -SO2CH2CH3, -SO2CH2CH2CH3, -SO2CH(CH3)2.

5. The compound of formula I according to claim 1, characterized in that R1 is selected from H, C1-C4 alkyl.

6. The compound of formula I according to claim 1, characterized in that R1 is selected from H, -CH3, -CH2CH3, -CH2CH2CH3, -CH(CH3)2.

7. The compound of formula I according to claim 1, characterized in that R2 and R3 are independently selected from H, C1-C4 alkyl, and C1-C4 alkyl-C(=O)-.

8. The compound of formula I according to claim 1, characterized in that R2 and R3 are independently selected from H, -CH3, -CH2CH3, -CH2CH2CH3, -CH(CH3)2, -COCH3, -COCH2CH3, -COCH2CH2CH3, -COCH(CH3)2.

9. A compound of formula II, in, R1 is H, C1-C6 alkyl; R2 and R3 are independently selected from H, C1-C6 alkyl, C1-C6 alkyl-C(=O)-; X1 and X2 are independently selected from H, halogen, nitro, cyano, halogenated C1-C6 alkyl; Y1, Y2, Y3, Y4 and Y5 are independently selected from H, halogen, C1-C6 alkyl, C1-C6 alkoxy, halogenated C1-C6 alkyl, C1-C6 alkyl-SO2-, nitro, cyano; and pesticide-acceptable salts thereof.

10. The compound of formula II according to claim 9, characterized in that R1 is selected from H or C1-C4 alkyl.

11. The compound of formula II according to claim 9, characterized in that R1 is selected from H, -CH3, -CH2CH3, -CH2CH2CH3, -CH(CH3)2.

12. The compound of formula II according to claim 9, characterized in that R2 and R3 are each independently selected from H, C1-C4 alkyl, C1-C4 alkyl-C(=O)-.

13. The compound of formula II according to claim 9, characterized in that R2 and R3 are each independently selected from H, -CH3, -CH2CH3, -CH2CH2CH3, -CH(CH3)2, -COCH3, -COCH2CH3, -COCH2CH2CH3, -COCH(CH3)2.

14. The compound of formula II according to claim 9, characterized in that X1 and X2 are independently selected from H, F, Cl, Br, I, nitro, cyano, and halogenated C1-C3 alkyl.

15. The compound of formula II according to claim 9, characterized in that X1 and X2 are independently selected from -F, -Cl, -Br, -I, -CF3, -CHF2, -NO2, -CN.

16. The compound of formula II according to claim 9, characterized in that Y1, Y2, Y3, Y4 and Y5 are independently selected from H, F, Cl, Br, I, C1-C4 alkyl, C1-C4 alkoxy, nitro, cyano, C1-C4 alkyl-SO2-, and halogenated C1-C3 alkyl.

17. The compound of formula II according to claim 9, characterized in that Y1, Y2, Y3, Y4 and Y5 are each independently selected from -F, -Cl, -Br, -I, -CH3, -CH2CH3, -CH2CH2CH3, -CH(CH3)2, -OCH3, -OCH2CH3, -OCH2CH2CH3, -OCH(CH3)2, -CF3, -CHF2, -NO2, -CN, -SO2CH3, -SO2CH2CH3, -SO2CH2CH2CH3, -SO2CH(CH3)2.

18. Compounds, and pesticidally acceptable salts of the above compounds.

19. A method for preparing the compound according to any one of claims 1 to 8, characterized in that: Its synthetic route is as follows: wherein R1, R2, R3, X, Y, n and m are as defined in claims 1 to 8, and R is methyl or ethyl.

20. A composition comprising the compound according to any one of claims 1 to 18.

21. The composition according to claim 20, characterized in that The composition further comprises a pesticidally acceptable adjuvant.

22. Use of the compound according to any one of claims 1 to 18 or the composition according to any one of claims 20 to 21 as a herbicide in agriculture.

23. A method for controlling undesirable weeds in useful plants, characterized in that Comprising the compound according to any one of claims 1 to 18 or the composition according to any one of claims 20 to 21.

24. The method according to claim 23, wherein The weeds are broadleaf weeds and / or grass weeds and / or sedge weeds; the useful plants are rice, wheat, corn, rapeseed and soybean.

25. The method according to claim 24, characterized in that The weeds are barnyard grass, Leptochloa chinensis, Dalbergia vaginalis, Alternanthera philoxeroides, Cyperus difformis and Polygonum syringae.

Images