Use of 3-isoxazolidinone compounds as selective herbicides

Abstract

The present application relates to the use of 3-isoxazolidinone compounds as selective herbicides. A herbicide composition containing 2-(2,4-dichlorophenyl)methyl-4,4-dimethyl-3-isoxazolidinone (2,4-DC) or 2-(2,5-dichlorophenyl)methyl-4,4-dimethyl-3-isoxazolidinone (2,5-DC) is described. A composition containing 2,4-DC or 2,5-DC and a second herbicide is also disclosed, wherein the combination does not contain both 2,4-DC and 2,5-DC. A method of using the composition is also described.

Description

[0001] This application is a divisional application of the international application number PCT / US2015 / 016892 filed on February 20, 2015, the Chinese national application number 201580009820.X, and the application titled “Use of 3-isoxazolidinone compounds as selective herbicides”.

[0002] CROSS-REFERENCE TO RELATED APPLICATIONS

[0003] This application claims the benefit of priority to U.S. Provisional Application No. 61 / 943,437, filed February 23, 2014, and U.S. Provisional Application No. 61 / 951,269, filed March 11, 2014, which are incorporated herein by reference in their entirety. Technical Field

[0004] The present invention relates to compositions and uses of at least one 3-isoxazolidinone analog herbicide selected from: 2-(2,4-dichlorophenyl)methyl-4,4-dimethyl-3-isoxazolidinone ("2,4-DC") and 2-(2,5-dichlorophenyl)methyl-4,4-dimethyl-3-isoxazolidinone ("2,5-DC"); including combinations with a second herbicide. Technical Background

[0005] The impact of protecting crops from undesirable plants (called weeds) is a long-term goal in agriculture, and weeds interfere with crop growth and can reduce crop yield. A method to achieve this goal is to develop selective herbicides, which can control weeds and can not show unacceptable phytotoxicity for the crops protected by demand. Recently, by genetically modifying crops to make them tolerant to non-selective herbicides (for example, glyphosate or glufosinate-ammonium) and applying the herbicide on such crops, crops are protected from weed threats. Unfortunately, this latter method has led to the evolution of weeds tolerant to herbicides, and the result is still necessary to selectively control the method for undesirable plants in crops.

[0006] U.S. Patent No. 4,405,357 discloses that certain 3-isoxazolidinones exhibit desirable selective herbicide activity. Specifically, such compounds are shown to be effective for controlling weedy and broad-leaved weed materials, while having no effect on legumes, particularly soybeans. The compounds specifically disclosed in this patent are 2-(2,4-dichlorophenyl)methyl-4,4-dimethyl-3-isoxazolidinone and 2-(2,5-dichlorophenyl)methyl-4,4-dimethyl-3-isoxazolidinone. Both compounds are effective for many weeds. However, there is still a need to reduce or eliminate damage to crops by using selective formulations, using an effective combination of herbicides, while not affecting the herbicidal action of the weeds to be controlled. Summary of the invention

[0007] The present invention meets this need. The present invention discloses novel compositions for protecting crops from undesirable plants. One aspect of the present invention relates to a composition comprising a first herbicide selected from the group consisting of: 2-(2,4-dichlorophenyl)methyl-4,4-dimethyl-3-isoxazolidinone ("2,4-DC") and 2-(2,5-dichlorophenyl)methyl-4,4-dimethyl-3-isoxazolidinone ("2,5-DC"); and at least one second herbicide, and the present invention also relates to its use for controlling undesirable plants that interfere with the growth of crops. Another aspect of the present invention relates to a composition comprising: a herbicide selected from the group consisting of 2-(2,4-dichlorophenyl)methyl-4,4-dimethyl-3-isoxazolidinone ("2,4-DC") and 2-(2,5-dichlorophenyl)methyl-4,4-dimethyl-3-isoxazolidinone ("2,5-DC"); at least one formulation component selected from the group consisting of an adjuvant for EC formulations, an adjuvant for SC formulations, and an adjuvant for CS formulations; and optionally, one or more additional active ingredients.

[0008] In at least one aspect of the invention, the disclosed composition contains 2,4-DC or 2,5-DC and a second herbicide different from the first herbicide, wherein when the first herbicide is 2,4-DC, the second herbicide is not 2,5-DC, and when the first herbicide is 2,5-DC, the second herbicide is not 2,4-DC. In one embodiment, the first herbicide is 2,4-DC. In another embodiment, the first herbicide is 2,5-DC.

[0009] In another embodiment, the second herbicide is selected from the group consisting of dimethenamid-P, diphenamid, naproxamide, naproxamide-M, naptalam, pethoxamid, propanil, acetochlor, alachlor, metolachlor, dimethachlor, S-metolachlor, pretilachlor, Benzofluor, camendichlor, chloramben, dicamba, bispyribac, pyrithiobac; mesotrione, sulcotrione, tefuryltrione, tembotrione, benfuresate, asulam, barban, alloxydim, isoxaflutole, dimethoate diinitramine, dipropalin, ethalfluralin, pendimethalin, trifluralin, acifluorfen, aclonifen, etnipromid, fluoronitrofen, fomesafen, imazamethabenz, bromobonil, bromoxynil, methiozolin, monomethoxalone (monisouron), pyroxasulfone, topramezone, bromofenoxim, clomeprop, 2,4-DEB, etnipromid, clacyfos, 4-CPA, 2,4-D, 2,4-DB, 3,4-DB, cloprop, 4-CPP, dichlorprop, chlorazifop, clodinafop, 2-(4-(4-chlorophenoxy)phenoxy)propionic acid (clofop),Cyhalofop, kuicaoxi, metamifop, propaquizafop, quizalofop, difenzoquat, halosulfuron, metazachlor, fluazolate, brompyrazon, clopyralid, diflufenican, atrazine, chlorazine, chlorazine cyanazine), cyprazine, trietazine, indaziflam, ametryn, methoprene, simetryn, terbutryn, ethiozin, hexazinone, metribuzin, amicarbazone, bencarbazone, carfentrazone, carfentrazone ethyl), sulfentrazone, thiencarbazone, cloransulam, isoproturon, linuron, methiuron, metobromuron, metoxuron, tetrafluron, thidiazuron, amidosulfuron, cyclosulfamuron, Ethoxysulfuron, flucetosulfuron, metsulfuron, prosulfuron, thifensulfuron, tebuthiuron, acrolein, flurtamone, fluthiacet-methyl, funaihecaoling, their agriculturally acceptable salts, their esters, and mixtures of two or more thereof.

[0010] In a preferred embodiment, the second herbicide is selected from the group consisting of acetochlor, aclonifen, ametryn, amicarbazone, atrazine, bispyribac-sodium, bromoxynil, carfentrazone, carfentrazone-ethyl ethyl), clomazone, cyhalofop, 2,4-D, 2,4-DB, 2,4-DEB, dicamba, diflufenican, dimethachlor, dimethenamid-P, ethalfluralin, ethoxysulfuron, flucetosulfuron, fluthiacet-methyl, fomesafen, hexazinone, isoxaflutole, linuron, mesotrione, metamifop, metazachlor or), metobromuron, S-metolachlor, metribuzin, metsulfuron, metsufluron-methyl, naproxenamide, pendimethalin, pethoxamid, pretilachlor, propanil, pyroxasulfone, quizalofop, tebuthiuron, thifensulfuron, thifensulfuron-methyl, trifluralin, their agriculturally acceptable salts, their esters, and mixtures of two or more thereof.

[0011] In another embodiment, the second herbicide is selected from the group consisting of naproxenamide, aclonifen, pyroxasulfone, metazachlor, diflufenican, sulfentrazone, mesotrione, metsulfuron, thifensulfuron, their agriculturally acceptable salts, their esters, and mixtures of two or more thereof.

[0012] In another aspect, a method of controlling undesirable vegetation and protecting crops is described, which uses a composition comprising: a first herbicide selected from 2,4-DC and 2,5-DC; and at least one second herbicide selected from the group consisting of acetochlor, aclonifen, ametryn, amicarbazone, atrazine, bispyribac, bromoxynil, carfentrazone, ethylcarfentrazone, and fentrazone-butyl. ethyl), clomazone, cyhalofop, 2,4-D, 2,4-DB, 2,4-DEB, dicamba, diflufenican, dimethachlor, dimethenamid-P, ethalfluralin, ethoxysulfuron, flucetosulfuron, fluthiacet-methyl, fomesafen, hexazinone, isoxaflutole, linuron, mesotrione, metamifop, metazachlor or), metobromuron, S-metolachlor, metribuzin, metsulfuron, metsufluron-methyl, naproxenamide, pendimethalin, pethoxamid, pretilachlor, propanil, pyroxasulfone, quizalofop, tebuthiuron, thifensulfuron, thifensulfuron-methyl, trifluralin, their agriculturally acceptable salts, their esters, and mixtures of two or more thereof.

[0013] In one embodiment, the susceptible crop includes plants selected from the group consisting of bananas, beans, beets, cassava, cereals, citrus, cocoas, coconuts, coffee, corn, cotton, fiber crops, flowers, forage corps, forestry, groundnuts, peanuts, hops, horticultures, non-land crops, oil palm, oilseed rape, peas, pomes, potatoes, rice, stone fruit, spices, sugar cane, sunflower, tea, tobacco, tomatoes, tree nuts, In at least one embodiment, the crop is selected from the group consisting of potato, soybean, corn, rice, sorghum, oilseed rape, barley, rye, cowpea, and canola.

[0014] Also described herein is a method of controlling undesirable plants in crops, comprising applying a herbicidally effective amount of a composition to a location of such plants. The composition comprises a first herbicide and a second herbicide. The first herbicide is selected from 2,4DC and 2,5DC. The second herbicide is different from the first herbicide. The crop is selected from the group consisting of potato, soybean, corn, rice, sorghum, rape, barley, rye, and rapeseed.

[0015] In another embodiment, the second herbicide is selected from the group consisting of dimethenamid-P, naproxenamide, dimethachlor, S-metolachlor, aclonifen, pyroxasulfone, metazachlor, diflufenican, sulfentrazone, metobromuron, metsulfuron, thifensulfuron, and agriculturally acceptable salts and esters thereof. DETAILED DESCRIPTION

[0016] As used in this application, unless otherwise indicated, the term "herbicide" refers to a composition mixture that is produced, sold or used in the field to kill or otherwise inhibit the growth of unwanted plants (such as but not limited to noxious or invasive weeds, broadleaf plants, herbs and sedges), which can be used for crop protection, building protection or turf protection. The term "herbicide" includes end-use herbicidal products. The composition can be a pure compound, a solution of a chemical compound, a mixture of chemical compounds, an emulsion, a suspension, a solid-liquid mixture, or a liquid-liquid mixture.

[0017] The term "herbicide" also refers to a product that is distributed through commercial channels from the manufacturer to the end user, who can use the herbicide in the form sold or in the form mixed with other excipients to affect the field.

[0018] The term "weeds" means and includes any plant that grows in an undesirable location.

[0019] The term "herbicidally effective amount" refers to the amount necessary to produce an observable herbicidal effect on the growth of unwanted plants, including one or more of the following: necrosis, mortality, growth inhibition, reproduction inhibition, proliferation inhibition and removal, destruction or reduction of the appearance and activity of unwanted plants.

[0020] The term "herbicidal composition" is defined to mean a herbicide, as well as any composition comprising a herbicidally active ingredient. The composition may be a solution or a mixture. In addition, the term "herbicidal composition" is defined to mean a product intended for use in manufacturing, or any product intended for formulation or repackaging into other agricultural products.

[0021] The term "herbicidal active ingredient" means an active ingredient in a herbicide that causes the herbicide to prevent, destroy, repel or mitigate any weeds. Other ingredients in the herbicide that are not herbicidal active ingredients are excipients that help to form, store or deliver the herbicidal active ingredient to the target. Examples of excipients in this embodiment include, but are not limited to, organic liquids in which the herbicidal active ingredient is dissolved, polyurea shells, water-soluble polymers, and one or more salts.

[0022] The term "2,4-DC" refers to 2-(2,4-dichlorophenyl)methyl-4,4-dimethyl-3-isoxazolidinone.

[0023] The term "2,5-DC" refers to 2-(2,5-dichlorophenyl)methyl-4,4-dimethyl-3-isoxazolidinone.

[0024] The composition herein can be in any conventional agriculturally available form, for example, in a two-pack form or in the form of a ready-made formulation or a tank-mixed formulation. Additionally, the active compound can be provided in any suitable formulation type (separately or premixed), for example, an emulsifiable concentrate (EC), a suspension concentrate (SC), a suspoemulsion (SE), a capsule suspension (CS), a water-dispersible granule (WG), an emulsifiable granule (EG), an oil-in-water emulsion (EO), an oil-in-water emulsion (EW), a microemulsion (ME), an oil dispersion (OD), an oil-miscible flowable animal (OF), an oil-miscible liquid (OL), a soluble concentrate (SL), an ultra-low volume suspension (SU), an ultra-low volume liquid (UL), a dispersible concentrate (DC), a wettable powder (WP), or any other technically feasible formulation in combination with an agriculturally acceptable adjuvant. In a preferred embodiment, the composition herein is supplied as an emulsifiable concentrate, a suspension concentrate or a capsule suspension.

[0025] At least one aspect of the present invention relates to a composition comprising a first herbicide selected from 2,4DC and 2,5DC; and a second herbicide, provided that when the first herbicide is 2,4DC or 2,5DC, the second herbicide is not 2,5DC or 2,4DC, respectively. Thus, the composition of the present invention contains 2,4DC or 2,5DC in combination with at least one other herbicide, wherein when the first herbicide is 2,4-DC, the second herbicide is not 2,5-DC, and when the first herbicide is 2,5-DC, the second herbicide is not 2,4-DC.

[0026] Thus, the composition of the present invention may be in any of the following forms: SC, SE, CS, WG, EC, EG, EO, EW, ME, OD, OF, OL, SL, SU, UL, DC, or WP formulations in combination with agriculturally acceptable adjuvants.

[0027] The second herbicide disclosed in the present invention includes the following, but is not limited thereto:

[0028] Acetyl-CoA carboxylase inhibitors (ACC), e.g. Cyclohexanone oxime ethers, such as alloxydim, clethodim, cloproxydim, cycloxydim, sethoxydim, tralkoxydim, butroxydim, clefoxydim or tepraloxydim; phenoxyphenoxypropionates, such as clodinafop-propargyl, cyhalofop-butyl, diclofop-methyl, fenoxaprop-ethyl, fenoxaprop-P-ethyl, fenthiazole-propionate; apropethyl), fluazifop-butyl, fluazifop-P-butyl, haloxyfop-ethoxyethyl, haloxyfop-methyl, haloxyfop-P-methyl, isoxapyrifop, propaquizafop, quizalofop-ethyl, quizalofop-P-ethyl or quizalofop-tefuryl; or an arylaminopropionic acid such as flamprop-methyl or flamprop-isopropyl;

[0029] Acetolactate synthase inhibitors (ALS), for example, imidazolinones, such as imazapyr, imazaquin, imazamethabenz-methyl (imazame), imazamox, imazapic or imazethapyr; pyrimidine ethers, such as pyrithiobac-acid, pyrithiobac-sodium, bispyribac-sodium. KIH-6127 or pyribenz oxym; sulfonamides, for example florasulam, flumetsulam or metosulam; or sulfonylureas, for example amidosulfuron, azimsulfuron, bensulfuron-methyl, chlorimuron-ethyl, chlorsulfuron, cinosulfuron, cyclosulfuron sulfamuron), ethametsulfuron-methyl, ethoxysulfuron, flazasulfuron, halosulfuron-methyl, imazosulfuron, metsulfuron-methyl, nicosulfuron, primisulfuron-methyl, prosulfuron, pyrazosul furon-ethyl), rimsulfuron, sulfometuron-methyl, thifensulfuron-methyl, triasulfuron, tribenuron-methyl, triflusulfuron-methyl, tritosulfuron, sulfosulfuron, foramsulfuron or iodosulfuron;

[0030] Amide For example, allidochlor (CDAA), benzoylprop-ethyl, bromobutide, chlorthiamid, diphenamid, etobenzanid, fluthiamide, fosamin or monalide;

[0031] At least one aspect of the present invention employs a second herbicide that provides enhanced safety and efficacy for controlling undesirable plants. In a more preferred embodiment, the herbicide employed enhances the selectivity of the effect on the crop to be treated. The following provides herbicides suitable for use as the second herbicide.

[0032] Amide herbicides Including but not limited to fenacet, amichlor, fluazifop, amine acid, benzylpyridin, bromobutyric acid, cafenstrole, CDEA, tricyclam, dimethoate (dimethoate-p), fenacet, triazole sulfamethoxam, etnipromid, tetrazopyralid, fluazifop-methyl, fluazifop-butyl, tiger power, halosafen, chloranil, isoxaben, naproxen, cypermethrin, pethoxydim, fenacet, quinazolam, pyrimidine oxadiazine, tebutam and tiafenacil and agriculturally acceptable salts and esters.

[0033] Anilide herbicides Including but not limited to dichlorvos, fenpyroxil, barnyardgrass, cyclohexane herbicides, erlujixiancaoan, etobenzanid, fenasulam, flufenacet, flufenican, ipfencarbazone, mefenacet, fluazifop, oxadiazine, cypermethrin, naphthamide, picolinafen, propanil, triafamone and agriculturally acceptable salts and esters.

[0034] Arylalanine herbicides include, but are not limited to, benzoylprop, flamprop, and flamprop-M, and agriculturally acceptable salts and esters thereof.

[0035] Acetylchloroanilide herbicideIncluding but not limited to acetochlor, alachlor, demechlor, butenesulfonamide, isobutachlor, acetochlor, dimethochlor, ethachlor, ethaprochlor, metazachlor, methamphetamine, S-methamyclothiachlor, pretilachlor, promethachlor, isomethachlor, clarithromycin, terbutachlor, methoxythiazide, xylachlor, sulfonanilide herbicides; benzofluor, cloransulam, diclosulam, florasulam, flumetsulam, metosulam, perfluidone, profluazol, and pyrimisulfan and agriculturally acceptable salts and esters thereof.

[0036] Sulfonamide herbicides Included are but not limited to asulam, carbasulam, fenasulam, oryzalin, penoxsulam, and pyroxsulam and agriculturally acceptable salts and esters thereof.

[0037] Thioamide herbicides Including but not limited to bencarbazone, and chlorthiamid and agriculturally acceptable salts and esters.

[0038] Benzoic acid herbicides Including but not limited to camendichlor, chloramben, dicamba, 2,3,6-TBA, tricamba, pyrimidinyloxybenzoic acid herbicides; bispyribac, and pyriminobac and agriculturally acceptable salts and esters.

[0039] Pyrimidinethiobenzoic acid herbicide Includes, but are not limited to, pyrithiobac and agriculturally acceptable salts and esters.

[0040] Phthalate herbicides These include, but are not limited to, chlorthal and agriculturally acceptable salts and esters.

[0041] Picoline herbicide Included are, but not limited to, aminopyralid, clopyralid, halauxifen, and picloram and agriculturally acceptable salts and esters.

[0042] Quinoline carboxylic acid herbicide Including but not limited to quinclorac, and quinmerac and agriculturally acceptable salts and esters.

[0043] Arsenic herbicides Including, but not limited to, cacodylic acid, CMA, DSMA, hexaflurate, MAA, MAMA, MSMA, potassium arsenite, and sodium arsenite and agriculturally acceptable salts and esters.

[0044] Benzoylcyclohexanedione herbicide Including but not limited to, fenquinotrione, ketospiradox, mesotrione, sulcotrione, tefuryltrione, tembotrione.

[0045] Benzofuranyl alkyl sulfonate / ester herbicide Includes, but are not limited to, benfuresate, and ethofumesate and agriculturally acceptable salts and esters.

[0046] Benzothiazole herbicides These include, but are not limited to, benazolin, benzthiazuron, fenthiaprop, mefenacet, and methabenzthiazuron and agriculturally acceptable salts and esters thereof.

[0047] Carbamate / ester herbicides Including, but not limited to, asulam, carboxazole, chlorprocarb, dichlormate, fenasulam, karbutilate, terbucarb and agriculturally acceptable salts and esters.

[0048] Phenyl carbamate herbicidesIncluding, but not limited to, avenaline, BCPC, carbasulam, recla, CEPC, chlorfenapyr, chlorpropham, CPPC, difenac, cotton amino, bendipine, ethyl bendipine, bendipine, and chlorpyrifos and agriculturally acceptable salts and esters thereof.

[0049] Carbonate herbicides These include, but are not limited to, bromobonil, dinofenate, and iodobonil and agriculturally acceptable salts and esters thereof.

[0050] Cyclohexene oxime herbicides: Included are but are not limited to fenacet, butadiene, clethodim, cloproxydim, cyclathione, cypermethrin, sethoxydim, pyraclostrobin, and chlorpyrifos.

[0051] Cyclopropylisoxazole herbicide Including, but not limited to, isoxachlortole, and isoxaflutole and agriculturally acceptable salts and esters.

[0052] Dicarboximide herbicides These include, but are not limited to, cinidon-ethyl, flumezin, flumiclorac, flumioxazin, and flumipropyn and agriculturally acceptable salts and esters thereof.

[0053] Dinitroaniline herbicides Including but not limited to benfluralin, butralin, chlornidine, diinitramine, dipropalin, ethalfluralin, fluchloralin, isopropalin, methalpropalin, nitralin, oryzalin, pendimethalin, prodiamine, profluralin, and trifluralin and agriculturally acceptable salts and esters.

[0054] Dinitrophenol herbicidesThese include, but are not limited to, dinofenate, dinoprop, dinosam, dinoseb, dinoterb, DNOC, etinofen, medinoterb, and agriculturally acceptable salts and esters thereof.

[0055] Diphenyl ether herbicide These include, but are not limited to, ethoxyfen and agriculturally acceptable salts and esters.

[0056] Nitrophenol ether herbicide Including but not limited to acifluorfen, beniflox, cypermethrin, chlorfenapyr, etnipromid, cyfluthrin, fluazifop-butyl, fluazifop-butyl, fomesafen, fucaomi, fluazifop-butyl, halosafen, lactofen, nitroprop-butyl, trifluorfen, and oxyfluorfen.

[0057] Dithiocarbamate / ester herbicides Including but not limited to dazomet, and metam and agriculturally acceptable salts and esters.

[0058] Halogenated aliphatic herbicides These include, but are not limited to, alorac, chloropon, dalapon, flupropanate, hexachloroacetone, methyl bromide, methyl iodide, monochloroacetic acid, SMA, and TCA and agriculturally acceptable salts and esters thereof.

[0059] Imidazolinone herbicides Including but not limited to imazamethabenz, imazamox, imazapic, imazapyr, imazaquin, imazethapyr and agriculturally acceptable salts and esters thereof.

[0060] Inorganic herbicides These include, but are not limited to, ammonium sulfamate, borax, calcium chlorate, cupric sulfate, ferrous sulfate, potassium diazonium compounds, potassium cyanate, sodium azide, sodium chlorate, and sulfuric acid and agriculturally acceptable salts and esters.

[0061] Nitrile herbicidesIncluding but not limited to bromobonil, bromoxynil, chloroxynil, dichlobenil, iodobonil, ioxynil, pyraclonil and agriculturally acceptable salts and esters thereof.

[0062] Organophosphorus herbicides Including but not limited to methyl amine glufosinate, amiprophos, safflower, disulfide, bialaphos, butylphos, clacyfos, 2,4-DEP, DMPA, EBEP, cypermethrin, glufosinate, glufosinate-P, glyphosate, huangcaoling, shuangjiaancaolin and agriculturally acceptable salts and esters.

[0063] Oxadiazole herbicides These include, but are not limited to, dimefuron, methazole, oxadiargyl, oxadiazon, and agriculturally acceptable salts and esters thereof.

[0064] Oxazole herbicides These include, but are not limited to, carboxazole, fenoxasulfone, isouron, isoxaben, isoxachlortole, methiozolin, monisouron, pyroxasulfone and topramezone and agriculturally acceptable salts and esters thereof.

[0065] Contains phenoxy herbicides Including but not limited to bromofenoxim, clomeprop, 2,4-DEB, difenopenten, disul, erbon, etnipromid, fenteracol, and trifopsime and agriculturally acceptable salts and esters thereof.

[0066] Phenoxyacetic acid herbicides Including but not limited to clacyfos, 4-CPA, 2,4-D, 3,4-DA, MCPA, MCPA-thioethyl, 2,4,5-T and agriculturally acceptable salts and esters.

[0067] Phenoxybutyric acid herbicide Including but not limited to 4-CPB, 2,4-DB, 3,4-DB, MCPB, 2,4,5-TB and agriculturally acceptable salts and esters

[0068] Phenoxypropionic acid herbicides Including but not limited to cloprop, 4-CPP, dichlorprop, dichlorprop-P, 3,4-DP, fenoprop, mecoprop, mecoprop-P and agriculturally acceptable salts and esters. Aryloxyphenoxypropionic acid herbicides include, but are not limited to, chlorazifop, clodinafop, clofop, cyhalofop, diclofop, fenoxaprop, fenoxaprop-P, fenthiaprop, fluazifop, fluazifop-P, haloxyfop, haloxyfop-P, isoxapyrifop, kuicaoxi, metamifop, propaquizafop, quizalofop, quizalofop-P, and trifop and agriculturally acceptable salts and esters thereof.

[0069] Phenylenediamine herbicides Including but not limited to dinitramine, and prodiamine and agriculturally acceptable salts and esters.

[0070] Pyrazole herbicides Including but not limited to azimsulfuron, difenzoquat, halosulfuron, metazachlor, metazosulfuron, pyrazosulfuron, pyroxasulfone and agriculturally acceptable salts and esters thereof.

[0071] Benzoylpyrazole herbicidesThese include, but are not limited to, benzofenap, pyrasulfotole, pyrazolynate, pyrazoxyfen, and topramezone and agriculturally acceptable salts and esters thereof.

[0072] Phenylpyrazole herbicides Included are, but are not limited to, fluazolate, nipyraclofen, pinoxaden, and pyraflufen and agriculturally acceptable salts and esters.

[0073] Pyridazine herbicides Included are, but not limited to, credazine, cyclopyrimorate, pyridafol, and pyridate and agriculturally acceptable salts and esters.

[0074] Pyridazinone herbicides Included are, but are not limited to, brompyrazon, chloridazon, dimidazon, flufenpyr, metflurazon, norflurazon, oxapyrazon, and pydanon and agriculturally acceptable salts and esters thereof.

[0075] Pyridine herbicides Including but not limited to aminopyralid, cliodinate, clopyralid, diflufenican, dithiopyr, flufenican, fluroxypyr, halauxifen, haloxydine, picloram, picolinafen, pyriclor, pyroxsulam, thiazopyr, and triclopyr and agriculturally acceptable salts and esters.

[0076] Pyrimidine diamine herbicide Including but not limited to iprymidam, and tioclorim and agriculturally acceptable salts and esters.

[0077] Pyrimidineoxybenzylamino herbicideIncluding but not limited to pyribambenz-isopropyl, pyribambenz-propyl quaternary ammonium herbicides; cyperquat, 1,1-bis[2-(diethylamino)-2-oxoethyl]-4,4-bipyridine (diethamquat), difenzoquat, diquat, morfamquat, paraquat and agriculturally acceptable salts and esters.

[0078] Thiocarbamate / ester herbicides Including but not limited to soda-killer herbicide, fenacet, avena citrate, EPTC, dicamba, isopolinate, methiobencarb, fenacet, cypermethrin, chlorpyrifos, benzylpyridinium, barnyardgrass, chlorpyrifos, chlorpyrifos, chlorpyrifos, and agriculturally acceptable salts and esters.

[0079] Thiocarbonate herbicides Includes, but are not limited to, dimexano, EXD, and proxan and agriculturally acceptable salts and esters.

[0080] Thiourea herbicides Included are, but not limited to, methiuron and agriculturally acceptable salts and esters.

[0081] Triazine herbicides These include, but are not limited to, dipropetryn, fucaojing and trihydroxytriazine and agriculturally acceptable salts and esters.

[0082] Chlorotriazine herbicides Examples include, but are not limited to, atrazine, clonazine, cyperazine, cyclohexine, eglinazine, cyperazine, mesoprazine, procyazine, glypozine, propazine, allazine, simazine, terbuthylazine, and thiazine and agriculturally acceptable salts and esters thereof.

[0083] Fluoroalkyl triazine herbicides Including but not limited to indaziflam, and triaziflam and agriculturally acceptable salts and esters.

[0084] Methoxytriazine herbicideThese include, but are not limited to, atraton, methometon, prometon, secbumeton, simeton, and terbumeton and agriculturally acceptable salts and esters thereof.

[0085] Methylthiotriazine herbicides Included are, but are not limited to, ametryn, aziprotryne, cyanatryn, desmetryn, dimethametryn, methoprene, prometryn, simetryn, and terbutryn and agriculturally acceptable salts and esters thereof.

[0086] Triazone herbicide Including but not limited to amethidione, amibuzin, ethiozin, hexazinone, isomethiozin, metamitron, and metribuzin and agriculturally acceptable salts and esters.

[0087] Triazole herbicides These include, but are not limited to, amitrole, cafenstrole, epronaz, and flupoxam and agriculturally acceptable salts and esters thereof.

[0088] Triadimefon herbicides Including but not limited to amicarbazone, bencarbazone, carfentrazone, carfentrazone ethyl, flucarbazone, ipfencarbazone, propoxycarbazone, sulfentrazone, and thiencarbazone and agriculturally acceptable salts and esters.

[0089] Triazolopyrimidine herbicidesIncluding but not limited to cloransulam, diclosulam, florasulam, flumetsulam, metosulam, penoxsulam, and pyroxsulam and agriculturally acceptable salts and esters.

[0090] Uracil herbicides Including but not limited to benzfendizone, bromacil, butafenacil, flupropacil, isocil, lenacil, saflufenacil, terbacil, and tiafenacil and agriculturally acceptable salts and esters.

[0091] Urea herbicide Including but not limited to benzthiazuron, cumyluron, cycluron, dichloralurea, diflufenzopyr, isonoruron, isouron, methabenzthiazuron, monisouron, and noruron and agriculturally acceptable salts and esters.

[0092] Phenylurea herbicides Including but not limited to anisuron, bromothuron, chloreturon, chlorotoluron, cypermethrin, chloreturon, oxazolidinone, diuron, fenuron, fluothiuron, isoproturon, linuron, mefenamic acid, methyl mefenamic acid, pyranuron, chloramuron, methoxuron, chlorothiocarb, mefenamic acid, parafluron, cypermethrin, cypermethrin, tetrafluron, thidiazuron and agriculturally acceptable salts and esters.

[0093] Sulfonylurea herbicidesIncluding but not limited to amidosulfuron-methyl, tetrazosulfuron-methyl, benzylsulfuron-methyl, chlorimuron-methyl, cyprosulfuron-methyl, ethoxysulfuron-methyl, flazol-methyl, flutosulfuron-methyl, flutosulfuron-methyl, pyrasulfuron-methyl, mesosulfuron, metazosulfuron, methiopyrisulfuron, monosulfuron, nicosulfuron, orthosulfamuron, epoxysulfuron, primisulfuron, propyrisulfuron, pyrazosulfuron-methyl, sulfosulfuron, sulfosulfuron-methyl, trifloxysulfuron and zuomihuanglong and agriculturally acceptable salts and esters.

[0094] Triazine sulfonylurea herbicides Including but not limited to chlorsulfuron, cinosulfuron, ethametsulfuron, iodosulfuron, iofensulfuron, and metsulfuron, prosulfuron, thifensulfuron, triasulfuron, tribenuron, triflusulfuron, tritosulfuron and agriculturally acceptable salts and esters.

[0095] Thiadiazole herbicide Included are but are not limited to buthiuron, ethidimuron, tebuthiuron, thiazafluron, and thidiazuron and agriculturally acceptable salts and esters.

[0096] Protoporphyrinogen oxidaseThe (PPO) inhibitor is selected from the group consisting of carfentrazone, carfentrazone-ethyl, sulfentrazone, fluthiacet-methyl, saflufenacil, diphenyl ethers, oxadiazoles, cyclic imides and pyrazoles.Examples of these PPOs include, but are not limited to, acifluorfen, acifluorfen-sodium, azafenidin, bifenox, butafenacil, chlomethoxyfen, chlornitrofen, ethoxyfen-ethyl, fluorodifen, fluoroglycofen-ethyl, fluoronitrofen, fluthiacet-methyl, fomesafen, furyloxyfen, halosafen, lactofen, nitrofen, nitrofluorfen, oxyfluorfen, flumiclorac-pentyl, fluazifop-butyl (flumioxazine), profluazol, pyrazogyl, oxadiargyl, oxadiazon, pentoxazone, fluazolate, pyraflufen-ethyl, benzfendizone, butafenacil, cinidon-ethyl, flumipropyn, flupropacil, fluthiacet-methyl, thidiazimin, azafenidin, carfentrazone, carfentrazone-ethyl, sulfentrazone, saflufenacil, flufenpyr-ethyl, ET-751, JV 485, nipyraclofen, or a mixture of two or more thereof. Preferably, the PPO inhibitor is selected from the group consisting of carfentrazone, sulfentrazone, fluthiacet-methyl, saflufenacil, and a mixture of two or more thereof.

[0097] Other herbicides Including but not limited to acrolein, allyl alcohol, cyprodinil, azopyrimidine, thiamethoxam, bentranil, benzobicyclonone, bicyclopyrone, butyrimidine, calcium cyanamide, chlorfenprop, fluazifop, cyproconazole, isocyanate, CPMF, cresol, ammonia, o-dichlorobenzene, piperidine, dimethyl disulfide, grass algae, azopyrimidine, fluridone, flurochloridone, furochloridone, funaihecaoling, glyphosate, glufosinate, herbimycin, huancaiwo, indole, methoxyphenone, methyl isothiocyanate, OCH, pelargonic acid, acid), pentachlorophenol, amyl oxazolidinone, phenylmercuric nitrate acetate, methylthiosulfuron, saflufenacil, cyclafenamide, algaquinone, thiocyanate, saflufenacil, sulglycapin, tavron, thidiazimin, cypermethrin, trimethoate, tripropindan, oxadiazine, and agriculturally acceptable salts and esters thereof.

[0098] In a preferred embodiment, the second herbicide is selected from the group consisting of dimethenamid-P, diphenamid, naproxamide, naproxamide-M, naptalam, pethoxamid, propanil, acetochlor, alachlor, dimethachlor, R / S-metolachlor, S-metolachlor, pretil achlor), benzofluor, cambendichlor, chloramben, dicamba, bispyribac, pyrithiobac; mesotrione, sulcotrione, tefuryltrione, tembotrione, benfuresate, asulam, barban, alloxydim, isoxafl utole), diinitramine, dipropalin, ethalfluralin, pendimethalin, trifluralin, acifluorfen, aclonifen, etnipromid, clomazone, sulfentrazone, fluoronitrofen, fomesafen, glyphosate, glufosinate nate), saflufenacil, imazamethabenz, bromobonil, bromoxynil, methiozolin, monisouron, pyroxasulfone, topramezone, bromofenoxim, clomeprop, 2,4-DEB, etnipromid, clacyfos, 4-CPA, 2,4-D, 2,4-DB, 3,4-DB,Cloprop, 4-CPP, dichlorprop, chlorazifop, clodinafop, clofop, cyhalofop, kuicaoxi, metamifop, propaquizafop, quizalofop, difenzoquat, halosulfuron, metazachlor, fluazolate, brompyrazon, clopyralid, fluazifop diflufenican, atrazine, chlorazine, cyanazine, cyprazine, trietazine, indaziflam, ametryn, methoprene, simetryn, terbutryn, ethiozin, hexazinone, metribuzin, amicarbazone, bencarbazone, carfentrazone, carfentrazone ethyl), sulfentrazone, thiencarbazone, cloransulam, isoproturon, linuron, methiuron, metobromuron, metoxuron, tetrafluron, thidiazuron, amidosulfuron, cyclosulfamuron, ethoxysulfuron, flucetosulfuron, metsulfuron, prosulfuron, thifensulfuron, tebuthiuron, acrolein, flurtamone, fluthiacet-methyl,Flunaihecaol (funaihecaoling), and its agriculturally acceptable salts and esters.

[0099] In a preferred embodiment, the second herbicide is selected from the group consisting of acetochlor, aclonifen, ametryn, amicarbazone, atrazine, bispyribac, bromoxynil, carfentrazone, carfentrazone ethyl ethyl), clomazone, cyhalofop, 2,4-D, 2,4-DB, 2,4-DEB, dicamba, diflufenican, dimethachlor, dimethenamid-P, ethalfluralin, ethoxysulfuron, flucetosulfuron, fluthiacet-methyl, fomesafen, glyphosate, glufosinate, saflufenacil, hexazinone, isoxaflutole, linuron, mesotrione, oxazole Metamifop, metazachlor, metobromuron, S-metolachlor, metribuzin, metsulfuron, metsufluron-methyl, napropamide, pendimethalin, pethoxamid, pretilachlor, propanil, pyroxasulfone, quizalofop, tebuthiuron, thifensulfuron, thifensulfuron-methyl, trifluralin, and agriculturally acceptable salts thereof, and esters thereof, and mixtures of two or more thereof.

[0100] In a more preferred embodiment, the second herbicide is selected from the group consisting of: dimethenamid-P, naproxamide, dimethachlor, S-metolachlor, aclonifen, pyroxasulfone, metazachlor, diflufenican, sulfentrazone, metobromuron, metsulfuron, thifensulfuron, and agriculturally acceptable salts and esters. In another embodiment, the second herbicide is selected from the group consisting of: metazachlor, naproxamide, sulfentrazone, and mesotrione.

[0101] In another embodiment, the first herbicide is 2,4DC and the second herbicide is selected from the group consisting of dimethenamid-P, pethoxamid, propanil, acetochlor, dimethachlor, pretilachlor, dicamba, bispyribac, mesotrione, ethalfluralin, pendimethalin, trifluralin. in), fomesafen, bromoxynil, 2,4-DEB, 2,4-D, 2,4-DB, cyhalofop, metamifop, quizalofop, atrazine, aclonifen, ametryn, hexazinone, metribuzin, amicarbazone, carfentrazone, carfentrazone ethyl ethyl), linuron, ethoxysulfuron, fluthiacet-methyl, naproxenamide, pyroxasulfone, metazachlor, diflufenican, metobromuron, metsulfuron, thifensulfuron, and agriculturally acceptable salts and esters thereof.

[0102] In another embodiment, the first herbicide is 2,5DC and the second herbicide is selected from the group consisting of dimethenamid-P, pethoxamid, propanil, acetochlor, dimethachlor, pretilachlor, dicamba, bispyribac, mesotrione, ethalfluralin, pendimethalin, trifluralin. in), fomesafen, bromoxynil, 2,4-DEB, 2,4-D, 2,4-DB, cyhalofop, metamifop, quizalofop, atrazine, aclonifen, ametryn, hexazinone, metribuzin, amicarbazone, carfentrazone, carfentrazone ethyl ethyl), linuron, ethoxysulfuron, fluthiacet-methyl, naproxenamide, pyroxasulfone, metazachlor, diflufenican, metobromuron, metsulfuron, thifensulfuron, and agriculturally acceptable salts and esters thereof.

[0103] In another embodiment, the second herbicide is any one of the following: dimethenamid-P, napropamide, dimethachlor, S-metolachlor, aclonifen, pyroxasulfone, metazachlor, diflufenican, sulfentrazone, metobromuron, metsulfuron, thifensulfuron, and agriculturally acceptable salts and esters thereof, having a particle size of less than 250, 100 or preferably less than 50 microns.

[0104] In another embodiment, the second herbicide can be any one of the following: napropamide, aclonifen, pyroxasulfone, metazachlor, diflufenican, sulfentrazone, mesotrione, metsulfuron, thifensulfuron, and agriculturally acceptable salts and esters thereof, having a particle size of less than 250, 100 or preferably less than 50 microns.

[0105] In one aspect of the invention, the composition of the invention selectively protects the following crops, which are any members of the following crop group: bananas, beans, beets, cassava, cereals, citrus, cocoa, coconuts, coffee, corn, cotton, fiber crops, flowers, forage crops, forestry, groundnuts, peanuts, hops, horticultures, non-land crops, oil palm, oilseed rape, peas, pomes, potato, rice, stone fruit, spices, sugarcane, sunflower, tea, tobacco, tomatoes, tree nuts. In at least one embodiment, the crop is potato, soybean, corn, rice, sorghum, oilseed rape, barley, rye, cowpea, or canola.

[0106] More specifically, such crops include, but are not limited to, bananas, plantains, beet: fodder, beets, sugar beets, cassava, barley, barley-spring, barley-winter, oats, oats+triticale-winter, oats-spring, oats-winter, rye, rye-winter, stubble, triticale, triticale+rye, wheat, wheat / barley, wheat-durum, wheat-spring, wheat-winter, citrus, grapefruit, uit), lemons / limes, oranges, cocoa, coconuts, coffee, corn, fodder corn, grain, sweet corn, corn+sorghum-spring, cotton, flax, carnation, chrysanthemum, flowers, gladioli, ornamentals: nursery plants, roses, alfalfa, kale: fodder, clover: seed, forage crops crops), grass-seed, pasture, rangeland, rye:seed, forestry, groundnuts, peanuts, hops, horticultures, industrial markets, aquatic weed, fallow land, idle crop land, land reclamation, summer fallow, oil palm,canola, rapeseed, rapeseed-spring, rapeseed-winter, linseed, lupin, mustard, oil seeds, safflower seed, sesame seed, olives, berries, blackberries, cranberries, raisins, durians, guavas, kiwifruit, lychees, mangoes, papayas, persimmons, pineapples, rambutans, strawberries, tropical fruits, beans, chickpeas, lentils, mung beans beans), peas, pulses / grams, apples, apricots, avocados, cherries, fruit, peaches, nectarines, pears, plums, pome fruit, pome / stone fruit, tree crops: wax apples, potatoes, potato seeds, sweet potatoes, rice, paddy rice, upland rice, rubber, millet, sm. grain: other, sorghum, soybeans, cardamom, cloves, ginsing, pepper: black, spices, sugar cane cane), sunflower, tea, tobacco, tomatoes, field tomatoes, green tomatoes, red tomatoes, almonds,betel nuts, cashews, hazelnuts, macadamia nuts, pecans, pistachios, walnuts, turf / lawns, agave, asparagus, brassicas: vegetable, broccoli, cabbage, Chinese cabbage, carrots, chicory, cruciferae, cucumbers, cucurbits, eggplant, garlic, herbs, lettuce, melons, onions, onions / garlic, peppers / chillies, field peppers, Japanese radish, squash, vegetable crops crops), field vegetables, other vegetables, watermelons, and grapes. Cucurbits include, but are not limited to, the following crops, such as melons: wax gourd (, Benincasa spp.), Citrullus spp. Citrullus spp.), Cucumber Cucumis spp.), Momordica Momordica spp.); Watermelon: Watermelon ( Citrullus lanatus ; Pumpkin: Cucurbita pepo; Squash: Cucurbita argyrosperma, C.ficifolia, C.maxima,) C.moschata and Cucumber: Cucumber (Cucumis sativus) In one embodiment, the crops include wheat varieties such as Bloc, Kord, Wyalkatchem and Mace.

[0107] In another aspect of the invention, the claimed compositions have selective action on weeds including, but not limited to, fleabane, sowthistle, grass weeds, broadleaf weeds, barnyardgrass (Echinochloa crus-galli), jimsonweed (Datura stramonium), velvetleaf (Abutilontheophrasti), common cockelbur (Xanthium strumarium) and hairy beggartickss (Bidens pilosa), Italian ryegrass (Lolium perenne.multiflorum), annual bluegrass (Poa annua), common lambsquarters (Chenopodium album), littleseed canarygrass (Phalaris minor), common chickweed (Stellaria media) and corn poppy (Papaver rhoeas), Pennsylvania smartweed (Polygonum pennsylvanicum), Palmer amaranth (Amaranthus palmeri), velvetleaf (Abutilon theophrasti), green foxtail (Setaria viridis), morningglory (Ipomoea spp.), yellow nutsedge (Cyperus esculentus), purple nutsedge (Cyperus rotundus) and bamboo leaf vegetable (Commelina benghalensis), Atriplex prostrate, Capsella bursa-pastoris, Chenopodium album, Chenopodium albumccentrorubrum, Desuraina Sophia, Galium aparine, Lamium Purpurum, Matricaria recutita, Solanum nigrum, Stellaria media, Viola arvensis.

[0108] In another embodiment, the activity of the first and second herbicides can be additive. Thus, when the observed activity is the same as expected, the activity of the combination is additive. In another embodiment, the combination of the first and second herbicides provides an activity greater than the expected addition, thereby providing synergy in the combination. Conversely, when the combined activity is less than expected, the activity is considered antagonistic. According to at least one aspect of the present invention, the combination of the first and second herbicides provides a synergistic effect for weed control.

[0109] In at least one embodiment, a synergistic effect of the combinations described herein is observed in the following: annual bluegrass, Benghal dayflower, black nightshade, blackgrass, cheat, common chickweed, common cocklebur, common lambsquarters, common ragweed, hairy beggarticks, Italian ryegrass, ivyleaf morningglory, jimsonweed, johnsongrass, littleseed canarygrass, Pennsylvania smartweed, pitted morningglory, purplenutsedge, quackgrass, shepherd's purse. purse), velvetleaf, wild buckwheat, wild mustard, wild oat, wild poinsettia, yellow nutsedge.

[0110] In another embodiment, a method of controlling undesirable plants in crops is described by applying a herbicidally effective amount of a composition containing: a first herbicide selected from 2,4-DC and 2,5-DC, and optionally, a second herbicide different from the first herbicide to the location of such plants, wherein the crop is selected from: wheat, potato, soybean, corn, rice, sorghum, rapeseed, barley, rye, cowpea, oat, sunflower, and rapeseed. In a more preferred embodiment, the crop is wheat, sunflower and rapeseed.

[0111] In at least one aspect of the invention, the composition of the present invention includes 2,4-DC or 2,5-DC, which can be applied before or after budding. The amount constituting the effective amount is variable and generally depends on many factors, such as soil type, expected rainfall pattern or irrigation, plants to be controlled, and the susceptibility of the specific crops involved. However, the effective amount that may be required per hectare is generally about 1-4000 grams of herbicidal active ingredients. Such compounds are generally applied at a ratio of 75-about 2000 grams of ai (active ingredient) / hectare. In a more preferred embodiment, the ratio of application amount is about 125-1500 grams of ai / hectare.

[0112] The composition of the present invention may also include one or more adjuvants or carriers. In at least one embodiment, the herbicidal active ingredient is present in a concentration range of 0.01% to about 95%. In another embodiment, agriculturally acceptable carriers account for about 4-98.5%. Surface active agents or surfactants, viscosity enhancers and solvents account for about 1-15% by weight of the final formulation, respectively. In a preferred embodiment, the composition of the present invention can be formulated as EC, SC or CS.

[0113] In another aspect of the invention, a specific composition is described containing only 2,4DC or 2,5DC in a suitable delivery vehicle. In one embodiment, the 2,4DC or 2,5DC content is about 25-40% w / w, the calcium chloride content is about 3-8% w / w, and the sodium nitrate content is about 3-8% w / w, while in another embodiment, the present invention may contain a 2,5DC formulation wherein the amount of 2,4DC is about 36% w / w, the amount of calcium chloride is about 6.156% w / w, and the amount of sodium nitrate is about 6.156% w / w.

[0114] In another aspect of the invention, the composition of the invention comprises: (i) a first herbicide selected from 2,4DC and 2,5DC; (ii) at least one inactive component selected from the group consisting of at least one antimicrobial agent, at least one surfactant, at least one thickener, at least one defoamer, at least one antifreeze agent, at least one solvent and at least one co-solvent; and (iii) optionally, one or more additional active ingredients.

[0115] In another aspect of the invention, a composition, for example in the form of a SC, is described which may contain a surfactant selected from a number of surfactants known in the art and commercially available. Surfactants may be divided into different classes, such as cationic surfactants, anionic surfactants, nonionic surfactants, ionic surfactants and amphiphilic surfactants. According to the invention, the surfactant may be any surfactant or a combination of two or more surfactants that can be used to dissolve the herbicide compound, for example, in its acid form, to produce a concentrate that forms a microemulsion.

[0116] Examples of some preferred surfactants include cationic, nonionic and anionic surfactants. Among them, some even more preferred classes of preferred surfactants include nonionic linear or branched ethoxylated alcohol surfactants, anionic phosphate surfactants (sometimes referred to as "phosphate" surfactants) and cationic ethoxylated tallow amine surfactants.

[0117] Suitable nonionic surfactants for use in the present invention include: ethoxylated linear alcohols, ethoxylated alkylphenols, alkyl EO / PO copolymers, polyalkylene glycol monobutyl ethers, ethoxylated fatty acids / oils, sorbitan laurate, polysorbate, sorbitan oleate, ethoxylated fatty acid alcohols or alkylphenols.

[0118] In another aspect of the invention, the composition of the invention may contain a thickener. Suitable thickeners are rice, starch, gum arabic, tragacanth, guar powder, English gum, starch ethers and esters, gum resins, galactomannan, magnesium aluminum silicate, xanthan gum, carrageenan, cellulose derivatives, methylcellulose, alginates and combinations thereof. Other known commercial products may include Lattice NTC 50, Lattice NTC 60, methylcellulose, clay, magnesium aluminum silicate silica (veegumsilica).

[0119] In another embodiment, the composition of the present invention may contain an antifreeze agent, for example, ethylene glycol, propylene glycol, urea, calcium chloride, sodium nitrate, magnesium chloride, and ammonium sulfate. Other inactive agents may include antimicrobial agents, such as Proxel GXL, Bronopol, BHT, BHA, Dowcided A Kathon; solvents include aromatic and linear solvents. Aromatic solvents include: aromatic 100, aromatic 150, aromatic 150ND, aromatic 200ND, isopar M, paraffin oil, Sunspray 6 or 11N, vegetable oil, methyl esters of fatty acids, dimethyl caprylamide. Defoamers such as Xiameter AFE-100, Dow Corning AFs, Dow Corning 1520, 1530, or 1540 may also be used in the claimed formulations.

[0120] At least another embodiment is directed to a composition comprising 2,4DC or 2,5DC in an amount of about 30-50% w / w, preferably about 35-45%, and more preferably about 40% w / w. In another embodiment, the composition of the present invention comprises an antifreeze in an amount of about 1-15%, preferably about 3-8%, and more preferably about 5-7% w / w. In another embodiment, the composition of the present invention comprises a surfactant in an amount of about 1-10%, preferably about 3-8%, and more preferably about 5-7% w / w. In one embodiment, the antifreeze is propylene glycol in an amount of about 3-8% w / w, and the surfactant is Tergiot in an amount of about 6% w / w.

[0121] In another aspect of the invention, a unique composition is described comprising: a first herbicide selected from 2-(2,4-dichlorophenyl)methyl-4,4-dimethyl-3-isoxazolidinone ("2,4-DC") and 2-(2,5-dichlorophenyl)methyl-4,4-dimethyl-3-isoxazolidinone ("2,5-DC"); and a second herbicide; provided that, when the first herbicide is 2,4DC or 2,5DC, the second herbicide is not 2,5DC or 2,4DC, respectively.

[0122] In a more preferred embodiment, the composition is in the form of a SC, which comprises at least one surfactant, a thickener and a solvent, and an optional defoamer. In another embodiment, the formulation is a CS formulation, which comprises a thickener, Reax or a lignin derivative, and a solvent. In another embodiment, the formulation is an EC formulation, which comprises a solvent, a surfactant, castor oil ethoxylation or nonylphenol and DDBS or its equivalent. In another aspect of the present invention, the composition of the present invention is prepared by the following method according to the following steps: an effective amount of herbicidal active ingredient is combined with a suitable surfactant, a desired amount of an emulsifier, a viscosity enhancer and a suitable solvent.

[0123] In another embodiment, the mixture is further subjected to a grinding process until a suitable particle size range of about 1-250 microns is obtained. In a preferred embodiment, the mixture is ground until 90% of the particle size (D90) is less than about 50 microns.

[0124] One aspect of the present invention relates to a composition comprising: i) a first herbicide selected from the group consisting of 2-(2,4-dichlorophenyl)methyl-4,4-dimethyl-3-isoxazolidinone ("2,4-DC") and 2-(2,5-dichlorophenyl)methyl-4,4-dimethyl-3-isoxazolidinone ("2,5-DC"); ii) at least one formulation component selected from the group consisting of an adjuvant for EC formulations, an adjuvant for SC formulations, and an adjuvant for CS formulations; and iii) optionally, one or more additional active ingredients.

[0125] The auxiliary agents for EC formulations can be selected from: pluronic or Tergitol, castor oil ethoxylation or nonylphenol, DDBS or its equivalent, and solvents. The auxiliary agents for SC formulations can be selected from: Tergitol, Pluronics, Dextrol, Soprophor FLK, glycols (Glycol), glycerine (Glycerine), water, defoamers, clays and thickeners. The auxiliary agents for CS formulations are selected from: solvents, polymeric materials, Reax or lignin derivatives, salts and thickeners such as xanthan gum. Generally, glycols can also be used as antifreeze agents in formulations of CS, EW, SE or SS types.

[0126] In one embodiment, the additional active ingredient is selected from: herbicides, such as clomozone. One embodiment of the composition includes: 2,4-DC, propylene glycol, and a surfactant. In a preferred embodiment, the composition includes about 36% by weight of 2,4-DC, about 6% by weight of propylene glycol, and about 3% by weight of the surfactant blend. Another embodiment of the composition includes: 2,4-DC, calcium chloride, and sodium nitrate. In a preferred embodiment, the composition includes about 36% by weight of 2,4-DC, about 6.156% by weight of calcium chloride, and about 6.156% by weight of sodium nitrate.

[0127] In another embodiment, an agricultural formulation is described herein that contains about 36% 2,4-dichlorophenyl-4,4-dimethyl-3-isoxazolidinone (410 g / L), about 6% propylene glycol, about 3% surfactant blend, and about 55% other ingredients, which may include agriculturally acceptable formulation ingredients known to those skilled in the art. In one embodiment, the agricultural formulation is a suspension concentrate (SC).

[0128] In another embodiment, the formulation contains about 36% 2-(2,4-dichlorophenyl)methyl-4,4-dimethyl-3-isoxazolidinone (430 g / L), about 6.156% calcium chloride hexahydrate (CAS No. 7774-34-7), about 6.156% sodium nitrate (CAS No. 7631-99-4), and about 51.69% other ingredients, which may include agriculturally acceptable formulation ingredients known to those skilled in the art. In one embodiment, the agricultural formulation is a capsule suspension (CS).

[0129] Another aspect of the present invention relates to a composition comprising: i) a first herbicide selected from 2-(2,4-dichlorophenyl)methyl-4,4-dimethyl-3-isoxazolidinone ("2,4-DC") and 2-(2,5-dichlorophenyl)methyl-4,4-dimethyl-3-isoxazolidinone ("2,5-DC"); and ii) a second herbicide; provided that, when the first herbicide is 2,4DC or 2,5DC, the second herbicide is not 2,5DC or 2,4DC, respectively. The second herbicide may be selected from the group consisting of dimethenamid-P, diphenamid, naproxamide, naproxamide-M, naptalam, pethoxamid, propanil, acetochlor, alachlor, dimethachlor, S-metolachlor, pretilachlor, benzofluor, camendichlor, chloramben, dicamba, bispyribac, pyrithiobac; mesotrione, sulcotrione, tefuryltrione, tembotrione, benfuresate, pyrithiobac asulam, barban, alloxydim, isoxaflutole, diinitramine, dipropalin, ethalfluralin, pendimethalin, trifluralin, acifluorfen, aclonifen, etnipromid, fluoronitrofen, fomesafen, imazamethabenz, bromobonil, bromoxynil, metiozolin, monisouron, pyroxasulfone, topramezone, bromofenoxim, clomeprop, 2,4-DEB, etnipromid,clacyfos, 4-CPA, 2,4-D, 2,4-DB, 3,4-DB, cloprop, 4-CPP, dichlorprop, chlorazifop, clodinafop, clofop, cyhalofop, kuicaoxi, metamifop, propaquizafop, quizalofop, difenzoquat, halosulfuron, metazachlor, fluazolate, brompyrazon, Clopyralid, diflufenican, atrazine, chlorazine, cyanazine, cyprazine, trietazine, indaziflam, ametryn, methoprotryne, simetryn, terbutryn, ethiozin, hexazinone, metribuzin, amicarbazone, bencarbazone, carfentrazone, carfentrazone ethyl), sulfentrazone, thiencarbazone, cloransulam, isoproturon, linuron, methiuron, metobromuron, metoxuron, tetrafluron, thidiazuron, amidosulfuron, cyclosulfamuron, ethoxysulfuron, flucetosulfuron, metsulfuron, prosulfuron, thifensulfuron, tebuthiuron, acrolein, flurtamone,Fluthiacet-methyl, funaihecaoling, and agriculturally acceptable salts thereof, and esters thereof, and mixtures of two or more thereof. In one embodiment, the second herbicide is selected from the group consisting of acetochlor, aclonifen, ametryn, amicarbazone, atrazine, bispyribac, bromoxynil, carfentrazone, carfentrazone ethyl ethyl), clomazone, cyhalofop, 2,4-D, 2,4-DB, 2,4-DEB, dicamba, diflufenican, dimethachlor, dimethenamid-P, ethalfluralin, ethoxysulfuron, flucetosulfuron, fluthiacet-methyl, fomesafen, hexazinone, isoxaflutole, linuron, mesotrione, metamifop, metazachlor, m etobromuron), S-metolachlor, metribuzin, metsulfuron, metsufluron-methyl, napropamide, pendimethalin, pethoxamid, pretilachlor, propanil, pyroxasulfone, quizalofop, tebuthiuron, thifensulfuron, thifensulfuron-methyl, sulfentrazone, trifluralin, and agriculturally acceptable salts thereof, and esters thereof, and mixtures of two or more thereof. In a preferred embodiment, the second herbicide is selected from the group consisting of napropamide, aclonifen,Pyroxasulfone, metazachlor, diflufenican, sulfentrazone, mesotrione, metsulfuron, thifensulfuron, and agriculturally acceptable salts thereof, and esters thereof, and mixtures of two or more thereof.

[0130] One aspect of the invention relates to a composition, wherein the first herbicide is 2,4-DC. Another aspect of the invention relates to a composition, wherein the herbicide is 2,5-DC.

[0131] In one aspect of the invention, the first herbicide of the composition is 2,4-DC, and the second herbicide can be selected from the group consisting of dimethenamid-P, diphenamid, naproxamide, naproxamide-M, naptalam, pethoxamid, propanil, acetochlor, alachlor, dimethachlor, S-metolachlor, pretilachlor. , benzofluor, cambendichlor, chloramben, dicamba, bispyribac, pyrithiobac; mesotrione, sulcotrione, tefuryltrione, tembotrione, benfuresate, asulam, barban, alloxydim, isoxaflutole, dimethoate diinitramine, dipropalin, ethalfluralin, pendimethalin, trifluralin, acifluorfen, aclonifen, etnipromid, fluoronitrofen, fomesafen, imazamethabenz, bromobonil, bromoxynil, methiozolin, monomethoxalone (monisouron), pyroxasulfone, topramezone, bromofenoxim, clomeprop, 2,4-DEB, etnipromid, clacyfos, 4-CPA, 2,4-D, 2,4-DB, 3,4-DB, cloprop, 4-CPP, dichlorprop, chlorazifop, clodinafop, 2-(4-(4-chlorophenoxy)phenoxy)propionic acid (clofop),Cyhalofop, kuicaoxi, metamifop, propaquizafop, quizalofop, difenzoquat, halosulfuron, metazachlor, fluazolate, brompyrazon, clopyralid, diflufenican, atrazine, chlorazine, chlorazine cyanazine), cyprazine, trietazine, indaziflam, ametryn, methoprene, simetryn, terbutryn, ethiozin, hexazinone, metribuzin, amicarbazone, bencarbazone, carfentrazone, carfentrazone ethyl), sulfentrazone, thiencarbazone, cloransulam, isoproturon, linuron, methiuron, metobromuron, metoxuron, tetrafluron, thidiazuron, amidosulfuron, cyclosulfamuron , ethoxysulfuron, flucetosulfuron, metsulfuron, prosulfuron, thifensulfuron, tebuthiuron, acrolein, flurtamone, fluthiacet-methyl, funaihecaoling, and agriculturally acceptable salts thereof, and esters thereof, and mixtures of two or more thereof. In one embodiment, the second herbicide is selected from the group consisting of acetochlor, aclonifen, ametryn,Amicarbazone, atrazine, bispyribac, bromoxynil, carfentrazone, carfentrazone-ethyl ethyl), clomazone, cyhalofop, 2,4-D, 2,4-DB, 2,4-DEB, dicamba, diflufenican, dimethachlor, dimethenamid-P, ethalfluralin, ethoxysulfuron, flucetosulfuron, fluthiacet-methyl, fomesafen, hexazinone, isoxaflutole, linuron, mesotrione, metamifop, metazachlor, m etobromuron), S-metolachlor, metribuzin, metsulfuron, metsufluron-methyl, naproxenamide, pendimethalin, pethoxamid, pretilachlor, propanil, pyroxasulfone, quizalofop, tebuthiuron, thifensulfuron, thifensulfuron-methyl, sulfentrazone, trifluralin, and agriculturally acceptable salts thereof, and esters thereof, and mixtures of two or more thereof. In a preferred embodiment, the second herbicide is selected from the group consisting of: dimethenamid-P, naproxenamide, dimethachlor, S-metolachlor, aclonifen, pyroxasulfone, metazachlor, diflufenican, sulfentrazone,Metobromuron, metsulfuron, thifensulfuron, and agriculturally acceptable salts thereof, and esters thereof, and mixtures of two or more thereof.

[0132] In another aspect of the invention, the first herbicide of the composition is 2,5-DC and the second herbicide can be selected from the group consisting of acetochlor, aclonifen, ametryn, amicarbazone, atrazine, bispyribac, bromoxynil, carfentrazone, carfentrazone ethyl ethyl), clomazone, cyhalofop, 2,4-D, 2,4-DB, 2,4-DEB, dicamba, diflufenican, dimethachlor, dimethenamid-P, ethalfluralin, ethoxysulfuron, flucetosulfuron, fluthiacet-methyl, fomesafen, hexazinone, isoxaflutole, linuron, mesotrione, metamifop, metazachlor, m etobromuron), S-metolachlor, metribuzin, metsulfuron, metsufluron-methyl, naproxenamide, pendimethalin, pethoxamid, pretilachlor, propanil, pyroxasulfone, quizalofop, tebuthiuron, thifensulfuron, thifensulfuron-methyl, sulfentrazone, trifluralin, and agriculturally acceptable salts thereof, and esters thereof, and mixtures of two or more thereof.In a preferred embodiment, the second herbicide is selected from: dimethenamid-P, naproxenamide, dimethachlor, S-metolachlor, aclonifen, pyroxasulfone, metazachlor, diflufenican, sulfentrazone, metobromuron, metsulfuron, thifensulfuron, and agriculturally acceptable salts thereof, and esters thereof, and mixtures of two or more thereof.

[0133] Another aspect of the present invention relates to a method for controlling undesirable plants in crops, comprising: applying to the locus of the plants a herbicidally effective amount of a composition comprising: a first herbicide selected from 2,4-DC and 2,5-DC, and a second herbicide, with the proviso that, when the first herbicide is 2,4-DC or 2,5-DC, the second herbicide is not 2,5-DC or 2,4-DC, respectively, wherein the crops can be selected from: broadleaf crops and forage crops, and the undesirable plants are selected from: grass weeds and broadleaf weeds. In one embodiment, the second herbicide is selected from the group consisting of dimethenamid-P, diphenamid, naproxamide, naproxamide-M, naptalam, pethoxamid, propanil, acetochlor, alachlor, dimethachlor, S-metolachlor, pretilachlor, benzofluor, camendichlor, chloramben, dicamba, bispyribac, pyrithiobac; mesotrione, sulcotrione, tefuryltrione, tesulfone mbotrione), benfuresate, asulam, barban, alloxydim, isoxaflutole, diinitramine, dipropalin, ethalfluralin, pendimethalin, trifluralin, acifluorfen, aclonifen, etnipromid, fluoronitrofen, fomesafen, imazamethabenz, bromobonil, bromoxynil, metiozolin, monisouron, pyroxasulfone, topramezone,Bromofenoxim, clomeprop, 2,4-DEB, etnipromid, clacyfos, 4-CPA, 2,4-D, 2,4-DB, 3,4-DB, cloprop, 4-CPP, dichlorprop, chlorazifop, clodinafop, clofop, cyhalofop, kuicaoxi, metamifop, propaquizafop, quizalofop, difenzoquat, halosulfuron, metazachlor, fl uazolate), brompyrazon, clopyralid, diflufenican, atrazine, chlorazine, cyanazine, cyprazine, trietazine, indaziflam, ametryn, methoprotryne, simetryn, terbutryn, ethiozin, hexazinone, metribuzin, amicarbazone, bencarbazone, carfentrazone, carfentrazone ethyl), sulfentrazone, thiencarbazone, cloransulam, isoproturon, linuron, methiuron, metobromuron, metoxuron, tetrafluron, thidiazuron, amidosulfuron, cyclosulfamuron, ethoxysulfuron, flucetosulfuron, metsulfuron, prosulfuron,Thifensulfuron, tebuthiuron, acrolein, flurtamone, fluthiacet-methyl, funaihecaoling, and agriculturally acceptable salts thereof, and esters thereof, and mixtures of two or more thereof. In another embodiment, the second herbicide is selected from the group consisting of acetochlor, aclonifen, ametryn, amicarbazone, atrazine, bispyribac, bromoxynil, carfentrazone, carfentrazone ethyl ethyl), clomazone, cyhalofop, 2,4-D, 2,4-DB, 2,4-DEB, dicamba, diflufenican, dimethachlor, dimethenamid-P, ethalfluralin, ethoxysulfuron, flucetosulfuron, fluthiacet-methyl, fomesafen, hexazinone, isoxaflutole, linuron, mesotrione, metamifop, metazachlor zachlor), metobromuron, S-metolachlor, metribuzin, metsulfuron, metsufluron-methyl, naproxenamide, pendimethalin, pethoxamid, pretilachlor, propanil, pyroxasulfone, quizalofop, tebuthiuron, thifensulfuron, thifensulfuron-methyl, sulfentrazone, trifluralin,and its agriculturally acceptable salts, and its esters, and mixtures of two or more thereof. In a preferred embodiment, the second herbicide is selected from the group consisting of dimethenamid-P, naproxenamide, dimethachlor, S-metolachlor, aclonifen, pyroxasulfone, metazachlor, diflufenican, sulfentrazone, metobromuron, metsulfuron, thifensulfuron, and its agriculturally acceptable salts, and its esters, and mixtures of two or more thereof. In one embodiment, the crop is selected from the group consisting of wheat, potato, soybean, corn, rice, sorghum, oilseed rape, barley, rye, cowpea, and canola. In a preferred embodiment, the crop is wheat.

[0134] In one aspect of the invention, the first herbicide of the method is 2,4-DC. In another method of the invention, the first herbicide is 2,5-DC.

[0135] In one embodiment of the method, the first herbicide is 2,4-DC and the second herbicide can be selected from the group consisting of dimethenamid-P, diphenamid, naproxamide, naproxamide-M, naptalam, pethoxamid, propanil, acetochlor, alachlor, dimethachlor, S-metolachlor, pretilachlor, fluorine Benzofluor, camendichlor, chloramben, dicamba, bispyribac, pyrithiobac; mesotrione, sulcotrione, tefuryltrione, tembotrione, benfuresate, asulam, barban, alloxydim, isoxaflutole, dimethoate dipropalin, ethalfluralin, pendimethalin, trifluralin, acifluorfen, aclonifen, etnipromid, fluoronitrofen, fomesafen, imazamethabenz, bromobonil, bromoxynil, methiozolin, monomethoxalone (monisouron), pyroxasulfone, topramezone, bromofenoxim, clomeprop, 2,4-DEB, etnipromid, clacyfos, 4-CPA, 2,4-D, 2,4-DB, 3,4-DB, cloprop, 4-CPP, dichlorprop, chlorazifop, clodinafop, 2-(4-(4-chlorophenoxy)phenoxy)propionic acid (clofop),Cyhalofop, kuicaoxi, metamifop, propaquizafop, quizalofop, difenzoquat, halosulfuron, metazachlor, fluazolate, brompyrazon, clopyralid, diflufenican, atrazine, chlorazine, chlorazine cyanazine), cyprazine, trietazine, indaziflam, ametryn, methoprene, simetryn, terbutryn, ethiozin, hexazinone, metribuzin, amicarbazone, bencarbazone, carfentrazone, carfentrazone ethyl), sulfentrazone, thiencarbazone, cloransulam, isoproturon, linuron, methiuron, metobromuron, metoxuron, tetrafluron, thidiazuron, amidosulfuron, cyclosulfamuron , ethoxysulfuron, flucetosulfuron, metsulfuron, prosulfuron, thifensulfuron, tebuthiuron, acrolein, flurtamone, fluthiacet-methyl, funaihecaoling, and agriculturally acceptable salts thereof, and esters thereof, and mixtures of two or more thereof. In one embodiment, the second herbicide is selected from the group consisting of acetochlor, aclonifen, ametryn,Amicarbazone, atrazine, bispyribac, bromoxynil, carfentrazone, carfentrazone-ethyl ethyl), clomazone, cyhalofop, 2,4-D, 2,4-DB, 2,4-DEB, dicamba, diflufenican, dimethachlor, dimethenamid-P, ethalfluralin, ethoxysulfuron, flucetosulfuron, fluthiacet-methyl, fomesafen, hexazinone, isoxaflutole, linuron, mesotrione, metamifop, metazachlor, m etobromuron), S-metolachlor, metribuzin, metsulfuron, metsufluron-methyl, naproxenamide, pendimethalin, pethoxamid, pretilachlor, propanil, pyroxasulfone, quizalofop, tebuthiuron, thifensulfuron, thifensulfuron-methyl, sulfentrazone, trifluralin and agriculturally acceptable salts thereof, and esters thereof, and mixtures of two or more thereof. In one embodiment, the second herbicide can be selected from: dimethenamid-P, naproxenamide, dimethachlor, S-metolachlor, aclonifen, pyroxasulfone, metazachlor, diflufenican, sulfentrazone,Metobromuron, metsulfuron, thifensulfuron, and agriculturally acceptable salts thereof, and esters thereof, and mixtures of two or more thereof.

[0136] In another embodiment of the method, the first herbicide is 2,5-DC, and the second herbicide can be selected from the group consisting of dimethenamid-P, diphenamid, naproxamide, naproxamide-M, naptalam, pethoxamid, propanil, acetochlor, alachlor, dimethachlor, S-metolachlor, pretilachlor. , benzofluor, cambendichlor, chloramben, dicamba, bispyribac, pyrithiobac; mesotrione, sulcotrione, tefuryltrione, tembotrione, benfuresate, asulam, barban, alloxydim, isoxaflutole, dimethoate diinitramine, dipropalin, ethalfluralin, pendimethalin, trifluralin, acifluorfen, aclonifen, etnipromid, fluoronitrofen, fomesafen, imazamethabenz, bromobonil, bromoxynil, methiozolin, monomethoxalone (monisouron), pyroxasulfone, topramezone, bromofenoxim, clomeprop, 2,4-DEB, etnipromid, clacyfos, 4-CPA, 2,4-D, 2,4-DB, 3,4-DB, cloprop, 4-CPP, dichlorprop, chlorazifop, clodinafop, 2-(4-(4-chlorophenoxy)phenoxy)propionic acid (clofop),Cyhalofop, kuicaoxi, metamifop, propaquizafop, quizalofop, difenzoquat, halosulfuron, metazachlor, fluazolate, brompyrazon, clopyralid, diflufenican, atrazine, chlorazine, chlorazine cyanazine), cyprazine, trietazine, indaziflam, ametryn, methoprene, simetryn, terbutryn, ethiozin, hexazinone, metribuzin, amicarbazone, bencarbazone, carfentrazone, carfentrazone ethyl), sulfentrazone, thiencarbazone, cloransulam, isoproturon, linuron, methiuron, metobromuron, metoxuron, tetrafluron, thidiazuron, amidosulfuron, cyclosulfamuron , ethoxysulfuron, flucetosulfuron, metsulfuron, prosulfuron, thifensulfuron, tebuthiuron, acrolein, flurtamone, fluthiacet-methyl, funaihecaoling, and agriculturally acceptable salts thereof, and esters thereof, and mixtures of two or more thereof. In one embodiment, the second herbicide may be selected from the group consisting of acetochlor, aclonifen, ametryn,Amicarbazone, atrazine, bispyribac, bromoxynil, carfentrazone, carfentrazone-ethyl ethyl), clomazone, cyhalofop, 2,4-D, 2,4-DB, 2,4-DEB, dicamba, diflufenican, dimethachlor, dimethenamid-P, ethalfluralin, ethoxysulfuron, flucetosulfuron, fluthiacet-methyl, fomesafen, hexazinone, isoxaflutole, linuron, mesotrione, metamifop, metazachlor, m etobromuron), S-metolachlor, metribuzin, metsulfuron, metsufluron-methyl, naproxenamide, pendimethalin, pethoxamid, pretilachlor, propanil, pyroxasulfone, quizalofop, tebuthiuron, thifensulfuron, thifensulfuron-methyl, sulfentrazone, trifluralin and agriculturally acceptable salts thereof, and esters thereof, and mixtures of two or more thereof. In a preferred embodiment, the second herbicide can be selected from: dimethenamid-P, naproxenamide, dimethachlor, S-metolachlor, aclonifen, pyroxasulfone, metazachlor, diflufenican, sulfentrazone,metobromuron, metsulfuron, thifensulfuron, and agriculturally acceptable salts thereof, and esters thereof, and mixtures of two or more thereof. In one embodiment of the method, the crop is wheat or corn. In a preferred embodiment, the crop is wheat.

[0137] Another aspect of the present invention relates to a method for controlling undesirable vegetation in a crop, the method comprising: applying to the locus of the plant a herbicidally effective amount of a composition comprising a first herbicide selected from the group consisting of 2,4-DC and 2,5-DC, wherein the crop can be selected from the group consisting of bananas, beans, beets, cassava, cereals, citrus, cocoas, coconuts, coffee, corn, fiber crops, flowers, forestry, forage crops, grapes, groundnuts, hops, horticultures, non-land crops, oil palm, oilseed rape, The crops may be selected from the group consisting of rape, peas, peanuts, pomes, potato, rice, spices, stone fruit, sugar cane, sunflower, tea, tobacco, tree nuts, turf, vegetable crops, vines, wheat, and undesirable plants selected from the group consisting of annual bluegrass, Benghal dayflower, blackgrass, black nightshade, broadleaf signalgrass, Canada thistle, cheat, common cocklebur (Xanthium pensylvanicum), common ragweed, cornpoppies, field violets, giant foxtail grass, foxtail), goosegrass, green foxtail, guinea grass, hairy beggarticks, herbicide-resistant blackgrass, horseweed,Italian ryegrass, jimsonweed, johnsongrass (Sorghum halepense), large crabgrass, littleseed canarygrass, morningglory spp., Pennsylvania smartweed, pitted morningglory, prickly sida, quackgrass, redroot pigweed, shattercane, shepherd's-purse, silky windgrass, sunflower (as a weed in potatoes), wild buckwheat (Polygonum convolvulus), wild mustard (Sinapis arvensis), wild oat (Avena fatua), wild poinsettia, yellow foxtail, yellow nutsedge (Cyperus sculentus). In one embodiment, the crop is selected from the group consisting of beets, cereals, corn, groundnuts, peanuts, oil palm, oilseed rape, peas, potato, rice, sugarcane, sunflower, tobacco, vegetable crops, and wheat. In a preferred embodiment, the crop is wheat.

[0138] In another preferred embodiment, a novel method for using 2,4DC or 2,5DC alone on the following crops is described, wherein the crops are bananas, beans, beets, cassava, cereals, citrus, cocoas, coconuts, coffee, fiber crops, flowers, forestry, forage corps, grapes, groundnuts, hops, horticultures, non-land crops, oil palm, oilseed rape, peas, pome, potato, spices, stone fruit, sugar cane, sunflower, tea, tobacco, tree nuts. In another embodiment, preferred crops are beets, cereals, corn, groundnuts, peanuts, oil palm, oilseed rape, peas, potato, rice, sugar cane, sunflower, tobacco, vegetable crops, and wheat.

[0139] In another preferred embodiment, a method of controlling undesirable plants and weeds using 2,4DC or 2,5DC alone is described to combat the following: annual bluegrass, Benghal dayflower, blackgrass, black nightshade, broadleaf signalgrass, Canada thistle, cheat, common cocklebur (Xanthium pensylvanicum), common ragweed, corn poppies, field violet, giant foxtail, goosegrass, green foxtail, guinea grass, hairy beggarticks, herbicide-resistant blackgrass. blackgrass), horseweed, Italian ryegrass, jimsonweed, johnsongrass (Sorghum halepense), large crabgrass, littleseed canarygrass, morning glory spp.), Pennsylvania smartweed, pitted morningglory, prickly sida, quackgrass, redroot pigweed, shattercane, sheppard's purse, silky windgrass, sunflower (as a weed in potatoes), wild buckwheat (Polygonum convolvulus), wild mustard (Brassica kaber), wild oat (Avena fatua), wild pointsettia, yellow foxtail, yellow nutsedge (Cyperus esculentus).

[0140] The following examples are only used to illustrate the invention and are not to be construed as limiting the scope of the invention in any way, because those skilled in the art will appreciate that further modifications may be made to the disclosed invention. All of these modifications are considered to be within the scope of the invention as defined in this specification and claims.

[0141] Example

[0142] Example 1: Suspension concentrate (SC) formulation of 2-(2,4-dichlorophenyl)methyl-4,4-dimethyl-3-isoxazolidinone (2,4-DC)

[0143] Formulation 1A: A SC formulation of 2,4-DC was prepared by mixing 37.89% 2,4-DC, 1.50% TERGITOL TM XD (Dow Chemical Company), 1.50% DEXTROL TM OC-180 (Ashland Specialty Company), 1.00% C, 0.10% AFE 100, 6.0% propylene glycol, 0.15% M Xanthan gum (CPKelco A Huber Company), 0.15% GXL, and 42.00% water (wt%).

[0144] In at least one embodiment, the following microencapsulation process is used to prepare the formulation of the present invention: before use, the slurry and discharge container, grinder, melt in a 55°C oven XD.

[0145] Preparation of KELZAN / diol slurry:

[0146] Into a separate container weigh propylene glycol. While stirring vigorously, slowly add KELZAN M. Mix until homogeneous.

[0147] Prepare the pre-grind slurry:

[0148] Add water to the mixing container and add to the tank AFE-100, XD, OC-180 and GXL, mix until homogeneous. Then add technical grade 2,4-DC portion by portion, mixing each portion of 2,4-DC in before adding more portions of 2,4-DC. Measure the starting viscosity.

[0149] Grinding steps:

[0150] Add a portion of the slurry to the attritor and grinder. Measure the particle size every 20 minutes and continue grinding until D90 < 10 microns. Drain the ground portion into a tared discharge tank and add the remaining portion of the pre-ground slurry. Grind the remaining portion as before and collect. Once grinding is complete, add 500 grams of holdback water to the attritor to rinse and combine with the grinding matrix. Record the weight and viscosity of the grinding matrix. Based on the weight recovery, determine the viscosity using the following calculation Amount of C added: C grams = (weight of recovered grinding matrix in grams / 9149.6) x 104. Then add C to mix thoroughly. Finally, add half of the / diol slurry, mixed for a minimum of 4 hours, submitted for in-process testing. The batch is stirred overnight. Viscosity should be measured after stirring is complete. Based on in-process testing and viscosity, add additional / glycol or water and stir.

[0151]

[0152] Formulation 1B: A SC formulation of 2,4-DC was prepared by mixing 44.1% 2,4-DC (42.0% active, AI), 1.5% TERGITOL TMXD (Dow Chemicals), 1.17% DEXTROL TM OC-180 (Ashland Specialty Chemicals), 6.0% propylene glycol, 0.13% A 2% aqueous solution of M xanthan gum (CP Kelco Huber) and 46.77% water (wt%) were ground until the particle size D90 was less than about 50 microns.

[0153] Preparation 1C SC formulation of 2,4-DC was prepared by mixing 44.0% 2,4-DC, 1.5% TERGITOL TM XD (Dow Chemical Company), ETHOX ERS 01293 (Ethox Chemicals), 6.0% propylene glycol, 0.13% A 2% aqueous solution of M xanthan gum (CP Kelco Huber), 0.15% DOW AF antifoam (Dow Chemical Company) and 46.7% water (all wt%) was ground until the particle size D90 was less than about 50 microns.

[0154] Formulation 1D: A SC formulation of 2,4-DC was prepared by combining 38% 2,4-DC (36% active AI), 1.17% TERGITOL TM XD (Dow Chemicals), 1.17% DEXTROL TM OC-180 (Ashland Specialty Chemicals), 0.078 AFE 100AF emulsion (Dow Chemical Company), 0.12PROXEL TM GXL Antimicrobial (Arch chemicals Inc.), 4.68% Propylene glycol, 3.0% AF (BASF), 1.0% C (MeadWestvaco), 0.12% A 2% aqueous solution of M xanthan gum (CP Kelco Huber) and 50.662% water (wt%) were mixed and the mixture was ground until the particle size D90 was less than about 50 microns.

[0155] Formulation 1E: A SC formulation of 2,4-DC was prepared by mixing 37.5% 2,4-DC, 1.5% DEXTROL TM ,1.5% TERGITOL TM XD, 1.0% C, 0.1% AFE 100, 0.15% GXL, 0.2% M, 6.0% propylene glycol, and 52.05% water.

[0156] Formulation 1F: SC preparation of 2,4-DC:

[0157]

[0158] Formulation 1G: SC formulation of 2,4-DC with sulfentrazone:

[0159]

[0160] Formulation 1H: SC formulation of 2,4-DC with diflufenac:

[0161]

[0162] Formulation II: SC formulation of 2,4-DC with methomyl:

[0163]

[0164] Example 2: Pre-emergence Herbicidal Evaluation of 2-(2,4-dichlorophenyl)methyl-4,4-dimethyl-3-isoxazolidinone in a Mixture with Metazachlor

[0165] The herbicidal efficiency of the compositions herein was tested in the following manner:

[0166] Dilute the mixture containing 2,4DC (Example 1B) and metazachlor ( S, 43.1% active ingredient, BASF) and a mixture of 2-(2,4-dichlorophenyl)methyl-4,4-dimethyl-3-isoxazolidinone and metazachlor to provide the appropriate test ratio concentration.

[0167] The crops tested were wheat and rapeseed (Brassica napus), and the weeds tested were ryegrass (IR) (Lolium perenne. multiflorum), bluegrass (AB) (Poa annua), lambsquarters (CL) (Chenopodium album), chrysanthemum (LC) (Phalaris minor), chickweed (CC) (Stellaria media), and poppy (CP) (Papaver rhoeas).

[0168] For pre-emergence testing, 4 disposable fiber flat plates (6"x10") were filled with top soil for the respective application rate of each herbicide solution and seeds of each material were planted in furrows made by pressing a template on top of the soil. After sowing, the furrows were covered with soil, watered well, and then the test compounds were applied.

[0169] The fiber flat plate for treatment is placed in a spray room with a static platform and a movable sprayer, with a nozzle height of 10.5 inches above the soil level. Once the sprayer is calibrated, a spray volume of 30 gallons per acre is sprayed with water, and the speed of the sprayer spraying the flat plate is such that a coverage equivalent of 30 gallons / acre is received. For the separate herbicidal solution and the herbicide composition of the present invention, the application rate is shown in Table 1 below. After treatment, the pre-emergence flat plate is immediately placed in a greenhouse and lightly watered. Afterwards, during the test, conventional watering and fertilization.

[0170] Weed control was evaluated for each experimental test at 21 days after treatment (DAT) for poppy and wheat and 28 DAT for all other materials. The results are shown as the average of the replicates, which were compared with the observations of the untreated control plates in the same test. The results are shown in Table 1 below. As shown, the efficacy of the combination of the present invention is far superior to that of the individual components.

[0171] Percent control is determined by a method similar to the 0-100 rating system disclosed in "Research Methods in Weed Science", 2nd edition, edited by B. Truelove, Southern Weed Science Association; Auburn University, Auburn, 1977. The rating system is as follows:

[0172]

[0173] Table 1: Percent crop injury and percent weed control at 21 and 28 days after treatment (DAT) with a mixture of 2,4-DC and metazachlor (3 or 4 replicates)

[0174]

[0175] Example 3: Pre-emergence Herbicidal Evaluation of 2-(2,4-dichlorophenyl)methyl-4,4-dimethyl-3-isoxazolidinone in a Mixture with Napropamide

[0176] The herbicidal efficiency of the compositions herein was tested in the following manner:

[0177] Dilute the mixture containing 2,4DC (Example 1C) and naproxenamide ( 50-DF, 50% active ingredient, a test composition from United Phosphorus Inc.) and a mixture of 2-(2,4-dichlorophenyl)methyl-4,4-dimethyl-3-isoxazolidinone and napropamide to provide the appropriate test rate concentration.

[0178] The crops tested were rapeseed (Brassica napus) and wheat, and the weeds tested were ryegrass (IR) (Lolium perenne. multiflorum), bluegrass (AB) (Poa annua), nigella (BG) (Alopecurus myosuroides), wild buckwheat (WB) (Polygonum convolvulus), chickweed (CC) (Stellaria media), caltrop (LC) (Phalaris minor) and wild oats (WO) (Avena fatua).

[0179] For pre-emergence testing, 4 disposable fiberboards (6"x10") were filled with top soil for each application score for each herbicide solution, and seeds of each material were planted in furrows made by pressing a template on top of the soil. The furrows with seeds were covered with soil and watered well before applying the test compound.

[0180] The fiber flat plate for treatment is placed in a spray room with a static platform and a movable sprayer, and the nozzle height is 10.5 inches above the soil level. Once the sprayer has been calibrated, 30 gallons of spray volume per acre are sprayed with water, and the speed of the spray flat plate of the sprayer makes it possible to receive 30 gallons / acre of coverage equivalent. For independent herbicidal solutions and herbicidal compositions of the present invention, the application ratio is shown in Table 2 below. After treatment, the flat plate before germination is immediately placed in a greenhouse and watered lightly. Afterwards, during the test period, conventional watering and fertilization. For all materials, after treatment (DAT) 27 days, weed control was evaluated for each experimental test. The results are shown as the mean value of replicates, which is compared with the observations of the untreated control flat plate in the same test.

[0181] The results are shown in Table 2 below. Thus, the compositions of the present invention provide much better results than each individual agent, respectively. Percent control is determined by a method similar to the 0-100 rating system disclosed in Research Methods in Weed Science, 2nd Edition, B. Truelove, ed., Southern Weed Science Association; Auburn University, Auburn, 1977.

[0182] Table 2: Percent crop injury and weed control at 27 days after treatment (DAT) with a mixture of 2,4-DC and naproxenamide (4 replicates)

[0183]

[0184]

[0185] The herbicidal efficiency of the compositions herein was tested in the following manner:

[0186] Dilute the mixture containing 2,4DC (Example 1B) and sulfentrazone ( 4F, 39.6% active ingredient, FMC Corporation) and a mixture of 2-(2,4-dichlorophenyl)methyl-4,4-dimethyl-3-isoxazolidinone and sulfentrazone to provide the appropriate test ratio concentrations.

[0187] The weeds tested were Pennsylvania Polygonum (PS) (Polygonum pennsylvanicum), Palmer Amaranth (PA) (Amaranthus palmeri), Vulgaris (VL) (Abutilon theophrasti), Green Setaria (GF) (Setaria viridis), Morning Glory (MG) (Ipomoea spp.), Yellow Sedge (YN) (Cyperus esculentus), Cyperus rotundus (PN) (Cyperus rotundus), and Bamboo Vegetable (BD) (Commelina benghalensis). The crops evaluated included corn, wheat, and cowpea.

[0188] For pre-emergence testing, 4 disposable fiberboards (6"x10") were filled with top soil for each application rate of each herbicide solution and seeds of each material were planted in furrows made by pressing a template on top of the soil. The furrows with crop / weed seeds were covered with soil and watered well before applying the test compound.

[0189] The plates to be treated were placed in a spray booth with a static platform and a movable sprayer with the spray head at a height of 10.5" above soil level. Once the sprayer was calibrated, a spray volume of 30 gallons per acre was applied with water, and the sprayer sprayed the plates at a rate that received 30 gallons / acre of coverage equivalent.

[0190] For the herbicidal solutions alone and the herbicide compositions of the present invention, the application rates are shown in Tables 3, 3A and 3B below. The pre-emergence plates were placed in a greenhouse immediately and lightly watered after treatment for herbicide activation. Afterwards, during the test period, conventional watering and fertilization were used. Weed control was evaluated for each experimental test at 28 days after treatment (DAT) and 14 DAT for crops. The results are shown as the average of the replicates, which were compared with the observations of the untreated control plates in the same test. The results are shown in Tables 3, 3A and 3B below. Percent weed control was determined by a method similar to the 0-100 rating system disclosed in Research Methods in Weed Science, Second Edition, B. Truelove, Southern Weed Science Association; Auburn University, Auburn, 1977.

[0191] Table 3: Percent weed control at 28 days after treatment (DAT) with a mixture of 2,4-DC and sulfentrazone (4 replicates)

[0192]

[0193]

[0194] Table 3A: Percent weed control at 28 days after treatment (DAT) with a mixture of 2,4-DC and sulfentrazone (4 replicates)

[0195]

[0196] Table 3B: Percent crop injury at 14 days after treatment (DAT) with a mixture of 2,4-DC and sulfentrazone (4 replicates)

[0197]

[0198]

[0199] Example 5: Pre-emergence Herbicidal Evaluation of 2-(2,4-dichlorophenyl)methyl-4,4-dimethyl-3-isoxazolidinone in a Mixture with Mesotrione

[0200] The herbicidal efficiency of the compositions herein was tested in the following manner:

[0201] Dilute the mixture containing 2,4DC Example 1C and mesotrione ( Herbicide, 40% active ingredient, a test composition from Syngenta) and a mixture of 2-(2,4-dichlorophenyl)methyl-4,4-dimethyl-3-isoxazolidinone and mesotrione to provide the appropriate test rate concentration.

[0202] The weeds tested were barnyardgrass (BG) (Echinochloa crus-galli), datura (PA) (Datura stramonium), venetum (VL) (Abutilon theophrasti), Pennsylvanian cocklebur (CC) (Xanthium strumarium), and hairy clover (HB) (Bidens pilosa). Crops evaluated included field corn and sorghum.

[0203] For pre-emergence testing, 4 disposable fiber flat plates (6"x10") were filled with top soil for the respective application rate of each herbicide solution and seeds of each material were planted in furrows made by pressing a template on top of the soil. After sowing, the furrows with seeds were covered with soil, watered well, and then the test compounds were applied.

[0204] The plates to be treated were placed in a spray booth with a static platform and a movable sprayer with the spray head at a height of 10.5" above soil level. Once the sprayer was calibrated, a spray volume of 30 gallons per acre was applied with water, and the sprayer sprayed the plates at a rate that received 30 gallons / acre of coverage equivalent.

[0205] For the individual herbicidal solutions and the herbicide compositions of the present invention, the application rates are shown in Table 4 below. Immediately after treatment, the pre-emergence plates were placed in a greenhouse and lightly watered. Thereafter, watering and fertilization were routinely applied during the test period. Weed control and crop injury were evaluated for each experimental test 28 days after treatment (DAT). The results are shown as the average of the replicates, which are compared to the observations of the untreated control plates in the same test, indicating much better efficacy than the individual component controls. The results are shown in Table 4 below. Percent control was determined by a method similar to the 0-100 rating system disclosed in Research Methods in Weed Science, 2nd Edition, B. Truelove, ed., Southern Weed Science Association; Auburn University, Auburn, 1977.

[0206] Table 4:Percent weed control at 28 days after treatment (DAT) with a mixture of 2,4-DC and mesotrione (4 replicates)

[0207]

[0208]

[0209] Example 6: Emulsifiable Concentrate (EC) Formulation of 2-(2,5-dichlorophenyl)methyl-4,4-dimethyl-3-isoxazolidinone (2,5-DC)

[0210] The EC formulation of 2,5-DC was prepared by mixing 46.5% 2,5-DC, 0.71% of a blend of 80% calcium dodecylbenzene sulfonate and 20% of a 6 mole adduct of nonylphenol with ethylene oxide, 5.47% of a blend of 60% calcium dodecylbenzene sulfonate and 40% of a 30 mole adduct of nonylphenol with ethylene oxide, 1.56 TERGITOL TM XD (Dow Chemical Company) and 45.689% Aormatic 100 fluid (ExxonMobil Chemical Company). The mixture was subjected to shear blending for about 1 minute and then stirred until a homogeneous mixture was obtained.

[0211] Example 7: Pre-emergence Herbicidal Evaluation of 2-(2,5-dichlorophenyl)methyl-4,4-dimethyl-3-isoxazolidinone The test composition of Example 6 containing 2,5-DC was diluted with water to provide the appropriate test rate concentration.

[0212] The weeds tested were Green Setaria (GF) (Setaria viridis), Black Grain (BG) (Alopecurus myosuroides) and Chickweed (CC) (Stellaria media). Crops evaluated included field corn and sorghum.

[0213] For pre-emergence testing, 4 disposable fiberboards (6"x10") were filled with top soil for each application rate of each herbicide solution and seeds of each material were planted in furrows made by pressing a template on top of the soil. The furrows were covered with soil and watered well before applying the test compound.

[0214] The plates to be treated were placed in a spray booth with a static platform and a movable sprayer with the spray head at a height of 10.5" above soil level. Once the sprayer was calibrated, a spray volume of 30 gallons per acre was applied with water, and the sprayer sprayed the plates at a rate that received 30 gallons / acre of coverage equivalent.

[0215] For the herbicidal solutions alone and the herbicidal compositions of the present invention, the application rates are shown in Table 5 below. Immediately after treatment, the pre-emergence plates were placed in a greenhouse and lightly watered. Thereafter, the plates were routinely watered and fertilized during the test. Weed control and crop damage were evaluated for each experimental test 28 days after treatment (DAT), and 14 DAT for the crop.

[0216]

[0217] Results are shown as the average of replicates, which were compared to the observations of untreated control plates in the same test. Results are shown in Table 5 below. Percent control was determined by a method similar to the 0-100 rating system disclosed in Research Methods in Weed Science, 2nd Edition, B. Truelove, ed., Southern Weed Science Association; Auburn University, Auburn, 1977.

[0218] Table 5: Percent control of weeds and crop damage using 2,5-DC EC formulations

[0219] Example 8: Emulsifiable Concentrate (EC) Formulation of 2-(2,4-dichlorophenyl)methyl-4,4-dimethyl-3-isoxazolidinone (2,4-DC)

[0220] Two different EC formulations of 2,4-DC were prepared using the procedure of Example 6 with the components and proportions shown in Table 6 below (with or without alkylphenol ethoxylate (APE)).

[0221] Table 6:

[0222]

[0223] *APE = Alkylphenol Ethoxylate

[0224] Example 9A: A capsule suspension (CS) formulation of 2,4-DC was prepared using the following microencapsulation process:

[0225] Organic phase: 36.29% 2,4-DC and 6.48% Aromatic 200ND.

[0226] Aqueous phase: 1.15% 88B, 5.33% sodium nitrate, 5.33% anhydrous calcium chloride, 3.68% 2% / 2% A mixture of 0.03% glacial acetic acid, 2.16% hexamethylenediamine (HMDA), 2.16% polymethylene polyphenyl isocyanate (polymer MDI; 27) and 37.39% water.

[0227] Feed rate: 420 g / min

[0228] Run time: 44.02 g / min

[0229] Organic feed rate: 209.78 g / min

[0230] Aqueous feed rate: 189.03 g / min

[0231] 27 Feed rate: 10.59 g / min

[0232] HMDA feed rate: 10.59 g / min

[0233] step:

[0234] First, heat the aqueous feed container and the organic feed container. Then heat the organic flushing unit to 80C to circulate the static mixer and heat the flushing solvent to 80C. Initially heat the microencapsulation unit to a target temperature of 85°C. Set the curing reactor temperature to 55°C and prepare for data entry.

[0235] Feed solution:

[0236] Add organic solvent to organic reactor preheated to 80-85C. Add 2,4-DC technical grade and warm to 80-85C. Maintain temperature with stirring until solution is clear and homogeneous. Complete the aqueous phase preparation. Prepare feeds of 43% HMDA, PAPI and 2% kelzan / 2% Proxel solution.

[0237] Unit setup and operation:

[0238] Next, circulate the organic flush to heat the static mixer and prepare it. Set up the PAPI and amine feed systems and start recirculating both lines at close to the set rate. Once the feed solutions and containers are at the set temperature, first add the aqueous feed system to the reactor tank. Hold the system until the set temperature is reached to the monitoring system, data log the fluctuating feed rate and wait until the system stabilizes. Once stable, transfer the organic phase to the organic feed tank. Hold until the feed is forward. Keep the organic flush solvent circulating. Set up a separate waste container to collect the 2,4-DC waste. Once ready, feed the aqueous phase forward to the waste container. Slowly increase the homogenizer rate to about 3000 rpm, feed the solvent flush within 30 seconds, and then immediately switch to the actual organic feed (this keeps the organic return line pre-prepared with solvent). Immediately increase the homogenizer RPM to the set level. Feed the amine and PAPI streams within 30 seconds. Manually control the feed rates to keep them close to the target level. Once closed, set the feed rate to automatic and set the target feed rate. Verify the system is running at the set feed rate. Once stable, feed forward to the cure reactor.

[0239] Curing reaction and inspection

[0240] Reactor maintained at 55°C for 4 hours. Cooled to room temperature. Added calcium chloride and sodium nitrate salts. Allowed to dissolve separately before adding more. Adjusted native pH to 6.0-7.5 with acetic acid if necessary. Added required amount of 2% Kelzan / 2% Proxel based on recovery and mixing. Sampled for evaluation and continued stirring until hydrated Kelzan Screen passed 200 mesh, filled, and physical properties completed.

[0241]

[0242] Example 9B: CS Formulation of 2,4-DC:

[0243]

[0244] Examples 9C-9E: CS Formulations of 2,4-DC:

[0245]

[0246] Examples 9F and 9G :CS preparation of 2,4-DC:

[0247] Examples 9F and 9G were prepared in separate batches from 255 gm 2,4-DC, 45 gm Aromatic 200ND, 31 gm PAPI 27, 288 gm water, 8 gm REAX 88B, 31 gm 43% HMDA and 37 gm sodium nitrate.

[0248] Biological tests

[0249] Considering "weed control", for the purposes of the present invention, weed control greater than or equal to 85% is acceptable and more importantly desirable. When weeds have greater than or equal to 85% damage, they cannot compete with crops for water, nutrients and physical space, minimizing the possibility of a significant decrease in crop yield. Typically, weed control is evaluated with 28DAT. For these considerations, synergy is evaluated at 28DAT, while crop safety is evaluated at 7 or 14DAT. The Colby method is used to evaluate synergy. The terms "synergy" and "synergy" or the term "in a synergistic manner" used herein refer to the interaction of two or more biologically active compounds in vivo, in this article, 3-isoxazolidinone compounds and a second active compound, so that when they are fed together, their combined effect is greater than the sum of the effects observed when they are fed separately. For example, the herbicidal effect of the combined feeding of 2,4-DC and the second agent described above and shown below. In this way, the application rate of the herbicidal combination can be lower than the registered use rate, thereby reducing the total chemical burden on the field where the combination is applied.

[0250] Colby's method of synergy is described in Colby, SR "Calculating Synergistic and Antagonistic Responses of Herbicide Combinations", Weeds, 1967, 15, pp. 20-22, which is incorporated herein by reference. According to this method, the presence of synergy between two active ingredients is established with the help of the Colby equation E = X + Y-(XY / 100). Using the Colby method, the presence of a synergistic interaction between two active ingredients is established in the following manner: First, the expected activity "E" of the mixture is calculated, which is based on the activity of the two components applied separately. In the above formula, "X" is the herbicidal activity expressed as a percentage control of the disclosed 3-isoxazolidinone when applied as a mixture at a rate "x". The term "Y" is the herbicidal activity of the second active when applied as a mixture at a rate "y". The equation calculates "E", the herbicidal activity of a mixture of "X" at a rate "x" and "Y" at a rate "y". If "E" is lower than the observed activity, synergy exists. If the herbicidal effect is strictly additive and there is no interaction, "E" will be equal to or higher than the observed activity. The table in the Examples below summarizes the % control of the tested weeds for the mixtures of the 3-isoxazolidinone compounds with other actives tested in all greenhouse samples and the expected values ​​relative to the observed % control. As used herein, control of the weed species is greater than or equal to 85%, for example, a 3-isoxazolidinone compound in combination with a second active ingredient will show synergy according to the Colby.

[0251] In at least one observation, one skilled in the art will appreciate that the compositions of the invention described herein provide synergistic weed control (with 85% cutoff) for at least 26 weed species. These species include bluegrass, Benghal dayflower, nightshade, black cumin, brome, chickweed, cocklebur, quinoa, ragweed, hairy clover, ryegrass, morning glory, datura, sorghum, small-seeded phragmites, pennsylvanian polygonum, bottomland yam, cyperus, lycopersicon, shepherd's purse, hemp, wild buckwheat, wild mustard, wild oats, wild poinsettia, yellow sedge. While the synergistic effect is at least one unexpected observation, one skilled in the art will expect that the improved safety of the combinations disclosed herein makes them particularly desirable in various stages of crop growth.

[0252] With regard to "crop injury", for the purposes of the present invention, the upper limit of acceptable crop injury (toxicity to plants) for most crops is 10%, since damage above 10% may result in significant crop yield reduction. Early crop safety is desirable (7-14 DAT) so that the crop can out-compete weeds for water, nutrients, and physical space. The following examples are submitted to further provide and highlight the findings of the bioassays according to the present invention.

[0253] Example 10: Weed control with a tank-mix combination of 2,4-DC and afenofop-butyl.

[0254] In this example, a greenhouse study was conducted to determine the weed efficacy of 2,4-DC when used alone or in combination with afenopibric as a pre-emergence (PRE) treatment on the following weeds: rush (Alopecurusmyosuroides, ALMOY), amaranth (Amaranthus retroflexus, AMARE), small-seeded phragmites (Phalaris minor, PHAMI), goosefoot (Chenopodium album, CHEAL), morning glory (Ipomoeahederacea, IPOHE), shepherd's purse (Capsella bursa-pastoris, CAPBP), wild oats (Avenafatua, AVEFA), wheatgrass (Elymus repens, AGRRE), bluegrass (Poa annua, POAAN), and nightshade (Solanum nigrum, SOLNI).

[0255] method:

[0256] 2,4-DC (CS 36.7%) was applied alone or as a tank mix with afenopyrin (53% WP) at 0, 125, 170, 210, or 250 g ai / ha, and the rate of afenopyrin applied alone or in a tank mix was 1500, 1800, or 2100 g ai / ha. Treatments 1-12 below of 2,4-DC and afenopyrin tank mix combinations met the same rates listed above. An untreated test was included as a reference standard. All plants were planted directly into 6x10" fiber flats with Pennington soil. Spartan was applied alone or in a tank mix at a rate of 1500, 1800, or 2100 g ai / ha. 39.6%), 280 g ai / ha, pendimethalin (Prowl EC, 37.4%), 784 g ai / ha, or S-methoxazole (Dual II 82.4%), 1084g ai / ha, as the commercial standard.

[0257] Treatments were replicated 3 times, with plates watered after planting but before treatments, and lightly watered after treatments were applied. Plates were then watered and fertilized daily. Treatments were performed with compressed air in an orbital atomizer at 30 GPA, using a TeeJet 8001E nozzle at 40 PSI. Visible percent weed control was recorded 14, 21, and 28 days after treatment (DAT), using a rating of 0 (no control) to 100 (complete plant death). Due to delayed germination, ratings were only performed at 21 and 28 DAT for Shepherd's Purse. Data (not included) were analyzed using Minitab statistical software with 95% confidence intervals.

[0258] Results for 28DAT:

[0259] All 12 tank mix combinations of 2,4-DC and benifloxacin gave ≥ 85% control of the following weeds: wild oats, pigweed, thin wheatgrass, nightshade, amaranth, small-seeded phragmites, annual bluegrass, blackgrass, and shepherd's purse. No combination controlled morning glory. 2,4-DC alone at 250 g ai / ha controlled pigweed and shepherd's purse for all rates (except 170 g).

[0260] At all 3 rates, for benifloxacin alone, quinoa, thin wheatgrass, amaranth, small-seeded phragmites, annual bluegrass, blackgrass, and shepherd's purse were controlled. 280 g of sulfentrazone controlled all weeds except thin wheatgrass, annual bluegrass, and blackgrass. 784 g of pendimethalin controlled 5 of the 10 weeds. 1064 g of S-methoxazolidinone controlled only 2 weeds. The table below highlights the data representing the unexpected synergy of the tested combinations.

[0261] Effect of 2,4-DC+benfenofop-(28DAT)-preemergence on wild oats at 28DAT

[0262]

[0263] α – measure of synergy, Y = yes; N = no

[0264] β and ρ - ratio - g ai / ha

[0265] 2,4-DC+benfenobene-(28DAT)-The effect of Solanum nigrum-28DAT

[0266]

[0267] α – measure of synergy, Y = yes; N = no

[0268] β and ρ - ratio - g ai / ha

[0269] Example 11: Pre-emergence (PRE) efficacy and canola selectivity of a tank-mix combination of 2,4-DC and clomazone.

[0270] In this example, a greenhouse study was conducted to determine the efficacy and canola injury when a tank-mix combination of 2,4-DC and clomazone was applied at different rates as a pre-emergence treatment against the following weeds: Amaranthus retroflexus (AMARE), morning glory (Ipomoea purpurea, PHBPU), wild mustard (Sinapisarvensis, SINAR), goosefoot (Chenopodium album, CHEAL), multiflorous ryegrass (Lolium multiflorum, LOLMU), chickweed (Stellaria media, STEME), corn poppy (Papaverrhoeas, PAPRH), and wild buckwheat (Polygonum convolvulus, POLCO). The crop tested was canola.

[0271] Materials and methods

[0272] To determine PRE efficacy and rapeseed injury, 2,4-DC (36.7% CS) at 4 rates and clomazone (Command 31.4%), either alone or as a tank mix. In combination treatments 1-12, 2,4-DC was applied at 125, 170, 210, or 250 g ai / ha and clomazone was applied at 60, 90, or 120 g ai / ha. Additional treatments included application of metazachlor ( 43.1%), 750 g ai / ha, Devrinol 50%), 1260 g, and dimethochlor ( 48%), 1000 g. Untreated tests were included as reference standards. Treatments were performed immediately after planting morning glory, wild mustard, quinoa, multiflora ryegrass, wild buckwheat, Amaranthus retroflexus, chickweed, corn poppy, and rapeseed.

[0273] Plants were grown in fiber flats (6"X10") containing Pennington soil and the flats were watered well before treatment and lightly after application. Flats were watered daily and fertilized after application of treatment. Each treatment was replicated 3 times. Treatments were applied with compressed air in an orbital spray chamber at 30 GPA using a TeeJet 8001E spray head at 40 PSI. Visible percent weed control and rapeseed injury were recorded 14, 21 and 28 days after treatment using a rating of 0 (no control / no injury) to 100 (total plant death).

[0274] Rapeseed injury ratings were blanching and wilting. Data (not included) were analyzed using Minitab statistical software with 95% confidence intervals.

[0275] Results for 28DAT:

[0276] Data collected at 28 DAT indicated that of the 12 2,4-DC and clomazone combinations, none of the combinations produced control of morning glory, wild mustard, Amaranthus retroflexus, and corn poppy. Eight combinations controlled quinoa, seven combinations controlled wild buckwheat, and three combinations controlled multiflora ryegrass. All 12 combinations controlled chickweed. Six 2,4-DC and clomazone combinations caused greater than 10% injury (whitening) to canola. Neither 2,4-DC or clomazone alone at any rate was able to control any species except chickweed. Metazamid controlled all weeds except tall morning glory and wild mustard. Napropamide controlled multiflora ryegrass, wild buckwheat, Amaranthus retroflexus, chickweed, and corn poppy. Dimethoate controlled only two species, multiflora ryegrass and corn poppy. All three herbicides, metazamid, naproxen, or dimethoate, were safe for canola at the rates mentioned in the methods.

[0277] In summary, all combinations of 2,4DC plus clomazone controlled chickweed (≥85%), while most combinations controlled pigweed and wild buckwheat. Six combinations were safe for canola (≤10% injury). The table below highlights the unexpected results observed for this study. The table below highlights the analysis of data representing the unexpected synergy of the tested combinations.

[0278] Effects of 2,4-DC+clomazone-(28DAT)-PREquinoa-28DAT

[0279]

[0280] α – measure of synergy, Y = yes; N = no

[0281] β and ρ - ratio - g ai / ha

[0282] Effects of 2,4-DC+clomazone-(28DAT)-PRE Lolium multiflorum-28DAT

[0283]

[0284] α – measure of synergy, Y = yes; N = no

[0285] β and ρ - ratio - g ai / ha

[0286] Effects of 2,4-DC+clomazone-(28DAT)-Fagopyrum serrata-28DAT

[0287]

[0288] α – measure of synergy, Y = yes; N = no

[0289] β and ρ - ratio - g ai / ha

[0290] Example 12: Weed Control and Crop Tolerance of 2,4DC and Dimethoate-P Combinations

[0291] In this example, a greenhouse study was conducted to determine pre-emergence weed efficacy and crop tolerance when 2,4-DC was applied alone or in combination with dimethoate-P. The weeds tested included: wild buckwheat (Polygonum convolvulus, POLCO), green hemp (Abutilon theophrasti, ABUTH), brome (Bromus secalinus, BROSE), wild oats (Avena fatua, AVEFA), radish (Raphanus sativus, RAPSN), poppy (Papaver rhoeas, PAPRH), golden foxtail (Setaria pumila, SETLU), multiflora ryegrass (Lolium perenne ssp.multiflorum, LOLMU). The crop tested was rapeseed.

[0292] method:

[0293] This greenhouse study was conducted to evaluate the effects of 2,4DC (CS 36.7%) and dimethoate-P ( 63.9%) tank mix combination for pre-emergence (PRE) weed control and rapeseed tolerance. 2,4-DC was applied alone or as a tank mix with 2,4-DC at 125, 170, 210, or 250 g ai / ha. For treatments Nos. 1-12, the application rates of 2,4-DC-P for tank mix application were 250, 375, or 500 g ai / ha, and 2,4-DC-P as a single application was applied at 750 g in addition to the above 3 rates. An untreated test was included as a reference standard.

[0294] All plants were planted directly in 6x10" fiber plates using Pennington soil. Butisan (43.1%) plus dimethazone-P were applied as a tank mix at 500 g each as a commercial standard. Treatments were replicated 3 times, plates were watered after planting but before treatments, and lightly watered after treatments were applied. Plates were then watered and fertilized daily. Treatments were applied with compressed air at 30 GPA in an orbital spray chamber using a TeeJet 8001E spray head at 40 PSI. Visible percent weed control and rapeseed injury were recorded 14, 21 and 28 days after treatment (DAT) using a rating of 0 (no control / no injury) to 100 (total plant death). Data (not included) were analyzed using Minitab statistical software with 95% confidence intervals.

[0295] Results for 28DAT:

[0296] All 12 tank-mix combinations of 2,4-DC with thiamethoxam-P gave ≥85% control of corn poppy, golden foxtail, and multifloral ryegrass. Bromus and wild oats gave control in 11 and 4 of the 12 tank-mix combinations, respectively. 2,4DC alone did not control any weed species at all rates. Thiamethoxam-P alone controlled bromus, corn poppy, golden foxtail, and multifloral ryegrass at all three rates. Control was observed for wild oats at 500 g or 750 gai / ha. The tank-mix treatment of metazachlor plus thiamethoxam-P controlled all weeds except hemp and radish.

[0297] All combinations of 2,4DC plus dimethazone-P were safe for rapeseed (≤10% injury). 2,4DC alone or fluazifop alone were safe for rapeseed. Metazachlor plus dimethazone-P were also safe for rapeseed.

[0298] In summary, the combination of 2,4DC and dimethazone-P controlled (≥85%) 5 of the 8 weeds. At the rates used in this study, 2,4DC alone had no control over any weeds; on the other hand, dimethazone-P had control over 5 weeds. In most cases, the combination of 2,4DC plus dimethazone-P was safe for rapeseed. The table below highlights the data representing the unexpected synergy of the tested combinations.

[0299] Effects of 2,4-DC+dimethathiachlor-P-Fagopyrum serrata-28DAT

[0300]

[0301] α – measure of synergy, Y = yes; N = no

[0302] β and ρ - ratio - g ai / ha

[0303] Effects of 2,4-DC+dimethathiachlor-P-wild oats-28DAT

[0304]

[0305] α – measure of synergy, Y = yes; N = no

[0306] β and ρ - ratio - g ai / ha

[0307] Example 13: Weed control with a combination of 2,4-DC and diflufenicol.

[0308] In this example, a greenhouse study was conducted to determine the weed efficacy of 2,4-DC when applied alone or in combination with diflufenicol for pre-emergence (PRE) treatments of the following weeds: blackgrass (Alopecurus myosuroides, ALMOY), silky wind grass (Apera spica-venti, APESV), retroflex amaranth (Amaranthus retroflexus, AMARE), small-seeded phragmites (Phalaris minor, PHAMI), wild buckwheat (Polygonum convolvulus, POLCO), green foxtail (Setaria viridis, SETVI), goosefoot (Chenopodium album, CHEAL), wild mustard (Sinapis arvensis, SINAR), morning glory (Ipomoea purpurea, PHPBU), shepherd's purse (Capsella bursa-pastoris, CAPBP).

[0309] method:

[0310] 2,4-DC (CS 36.7%) was applied alone or as a tank mix with diflufenicol at 125, 170, 210, or 250 g ai / ha. Diflufenicol rates applied alone or in a tank mix were 50, 75, or 100 g ai / ha. All plants were planted directly in 6x10" fiber flats with Pennington soil. Pyroxasulfone (KIH-485, 85%), 74.3 g ai / ha, Prowl The treatments were repeated three times, with plates watered after planting but before treatment and lightly watered after application of treatments. Plates were then watered and fertilized routinely. Treatments were applied with compressed air at 30 GPA in an orbital spray chamber using a TeeJet 8001E spray head at 40 PSI.

[0311] Visible percent weed control was recorded at 14, 21 and 28 DAT using a rating of 0 (no control) to 100 (complete plant death). Data (not included) were analyzed using Minitab statistical software with 95% confidence intervals.

[0312] Results for 28DAT:

[0313] All 12 tank mix combinations of 2,4-DC and diflufenican gave ≥85% control of the following weeds: silkweed, amaranth, green foxtail, quinoa, and shepherd's purse. Control of blackgrass was noted when 2,4DC was applied at 250 g (with diflufenican at a rate greater than or equal to 75 g ai / ha). Complete control of wild buckwheat was observed for 2,4DC (210 g) plus diflufenican (75 g). Adding diflufenican at 100 g to 2,4DC at any rate controlled (≥85%) wild mustard.

[0314] 2,4DC alone had no control on most plants at all rates except shepherd's purse. Diflufenac alone controlled silkweed, amaranth, green foxtail and shepherd's purse to some extent at all three rates. Wild buckwheat and wild mustard were controlled at 75 g or higher. Diflufenac controlled pigweed only at 100 g. Pirowei controlled all weeds except morning glory and shepherd's purse at 74.3 g. Pendimethalin controlled 6 of 10 weeds at 1,200 g. Chlorsulfuron plus methylsulfuron controlled all 10 weeds except black cumin and small seed bee at 15.8 g.

[0315] In summary, the combination of 2,4DC and diflufenicol controlled (≥85%) 8 of the 10 weeds. For all rates used in this study, 2,4DC alone had control on one weed, while diflufenicol alone had control on 7 weeds. The table below highlights the data representing the unexpected synergy of the tested combinations.

[0316] Effects of 2,4-DC+pyrifos on Nigella sativa L. at 28DAT

[0317]

[0318] α – measure of synergy, Y = yes; N = no

[0319] β and ρ - ratio - g ai / ha

[0320] Effects of 2,4-DC+pyrifos on -28DAT of Chenopodium album

[0321]

[0322] α – measure of synergy, Y = yes; N = no

[0323] β and ρ - ratio - g ai / ha

[0324] Effects of 2,4-DC+pyrifos on -28DAT of Brassica juncea

[0325]

[0326] α – measure of synergy, Y = yes; N = no

[0327] β and ρ - ratio - g ai / ha

[0328] Example 14: POST crop selectivity and weed control of 2,4-DC and bromoxynil combinations.

[0329] In this example, greenhouse studies were conducted to investigate post-emergence (POST) weed control and selectivity for wheat and barley of 2,4DC alone or in a tank mix in combination with bromoxynil on wild oats (Avenafatua, AVEFA), wild buckwheat (Polygonum convolvulus, POLCO), chickweed (Stellariamedia, STEME), quinoa (Chenopodium album, CHEAL), wild mustard (Sinapis arvensis, SINAR), and multiflora ryegrass (Lolium multiflorum, LOLMU). The study also evaluated post-emergence crop safety for wheat and barley.

[0330] method:

[0331] 2,4-DC (SC 36%) was applied alone or as a tank mix with bromoxynil at 125, 170, 210, or 250 g ai / ha. Application rates of bromoxynil alone or as a tank mix were 140, 210, or 280 g ai / ha. Thifensulfuron-methyl + tribenuron-methyl + metsulfuron-methyl (Accurate Extra, 37.5% + 18.75% + 15%), 31.48 g ai / ha, or thifensulfuron-methyl + tribenuron-methyl (Harmony Extra SG, 33.33% + 16.67%), 19.95 g ai / ha, were applied as commercial standards, and an untreated control was included for comparison. The commercial standard application included a nonionic surfactant (0.5% (v / v)). No adjuvant was applied for any of the other treatments. All plants were planted directly into 3" plastic pots using metro-mix as the growing medium. Pigweed was 1.75", chickweed was 2", wild mustard was 2.25", wild oats was 5.5", wild buckwheat was 2-5", multiflora ryegrass was 2-3", wheat was 5.5", and barley was 4.5" in height at the time of treatment application. Plants were well watered before application and not watered for 24 hours after application. Plants were watered and fertilized daily after treatment application. Each treatment was replicated 4 times. Treatments were applied with compressed air in an orbital spray chamber at 30 GPA using a TeeJet 8001E spray head at 40 PSI.

[0332] Visible percent wheat and barley injury and weed control were recorded 14, 21 and 28 days after treatment (DAT) using a rating scale of 0 (no control / no crop injury) to 100 (total plant death). Data (not included) were analyzed using Minitab statistical software with 95% confidence intervals.

[0333] Results for 28DAT:

[0334] All tank mix applications of 2,4-DC (SC 36%) plus bromoxynil had ≥ 85% control of wild buckwheat and wild mustard, 11 combinations controlled pigweed, and 3 combinations controlled chickweed. No tank mix combinations controlled wild oats and multifloral ryegrass, however, some combinations suppressed multifloral ryegrass (70-84% injury).

[0335] None of the combinations injured wheat, 1 combination caused moderate injury to barley and barley was safe to all other tank mix combinations. 2,4-DC (SC 36%) applied alone did not control any of the weeds evaluated and was safe to both wheat and barley at all rates. Bromoxynil alone controlled wild buckwheat, wild mustard, and pigweed at all rates and was safe to both crops at all rates. Thifensulfuron-methyl + benzylsulfuron-methyl + benzylsulfuron-methyl or Thifensulfuron-methyl + benzylsulfuron-methyl both controlled wild buckwheat, wild mustard, chickweed, and pigweed and were safe to barley and wheat; no treatments controlled wild oats or ryegrass.

[0336] In the evaluation, no random application controlled Lolium multiflorum. However, it was observed that when 2,4-DC (SC 36%) was applied at ≥ 210 g ai / ha (with random rates of bromoxynil), the level of injury to Lolium multiflorum increased to inhibition levels in all cases. This same level of control was not achieved by either herbicide applied alone.

[0337] In summary, POST applications of all 12 2,4-DC and bromoxynil tank mix combinations controlled (≥85%) wild mustard and wild buckwheat, 11 combinations controlled quinoa, and 3 combinations controlled chickweed. Wild oats and multiflora ryegrass were not controlled by any combination. All combinations except one were safe for barley and wheat. 2,4-DC alone did not control any of the test weeds in this example, and bromoxynil alone controlled wild buckwheat, wild mustard, and quinoa. The table below highlights the data representing the unexpected synergy of the tested combinations.

[0338] Effects of 2,4-DC+bromobenzonitrile-3129(28DAT)-Chickenia fasciata-28DAT

[0339]

[0340] α – measure of synergy, Y = yes; N = no

[0341] β and ρ - ratio - g ai / ha

[0342] Example 15: Pre-emergence (PRE) weed efficacy and corn selectivity of a 2,4-DC and S-methoxazole tank-mix combination.

[0343] In this example, a greenhouse study was conducted to determine the weed efficacy of 2,4-DC in a tank mix combination combined with S-methoxazol applied to corn at different rates. The weeds tested in this study were: Amaranthus retroflexus (AMARE), Datura stramonium (DATST), Solanum nigrum (SOLNI), Digitaria sanguinalis (DIGSA), Polygonum pensylvanicum (POLPY), Conyza canadensis (ERICA), Polygonum convolvulus (POLCO). The crop tested was corn (var. Viking).

[0344] method:

[0345] To determine PRE efficacy and corn injury, 2,4-DC (36.7% CS) and S-methoxazole were applied at five rates, either alone or as a tank mix. 2,4-DC was applied at 0, 125, 170, 210, or 250 g ai / ha, and S-methoxazole was applied at 0, 267, 534, 801, or 1070 g ai / ha. Additional treatments included 169.9 g ai / ha of pyraclostrobin plus fluazifop-methyl (Anthem TM 23.3%), and 123 g of mesotrione ( 40%) plus 1252 g of S-methoxazole. Treatments were applied immediately after planting crabgrass, datura, nightshade, amaranth, Pennsylvanian knotweed, Canadian thorn grass, wild buckwheat and corn. Untreated tests were included as reference standards.

[0346] Weeds were planted in fiber flats (6"X10") containing Pennington soil and the flats were watered well before application and lightly after application. Flats were watered daily and fertilized after treatment application. Each treatment was replicated 3 times. Treatments were applied with compressed air in an orbital spray chamber at 30 GPA using a TeeJet 8001E spray head at 40 PSI. Visible percent weed control and corn injury were recorded 14, 21 and 28 days after treatment using a rating of 0 (no control / no injury) to 100 (complete plant death). Corn injury was rated as blanching and wilting. Data (not included) were analyzed using Minitab statistical software with 95% confidence intervals.

[0347] result:

[0348] All 16 combinations controlled (≥85%) Crabgrass, Solanum nigrum, Amaranthus retroflexus, Polygonum pennsylvanicum, and Canada thorn. Nine combinations controlled Datura stramonium, while only three combinations controlled Fagopyrum serrata.

[0349] All 16 combinations caused less than or equal to 5% corn leaf blanching, while 12 combinations caused greater than 10% corn wilt. 2,4-DC alone controlled large crabgrass at 170 g ai / ha or 250 g and was safe for corn at all rates. S-Methochlor alone had control of all weeds at different rates, except for Datura. At 267 g or 534 g, S-Methochlor alone caused less than 10% corn blanching or wilt. Premixes of Pirovir plus flumethoxetine, and tank mixes of mesotrione plus S-Methochlor controlled all species, except Pirovir plus flumethoxetine, which did not control Datura. Corn injury for Pirovir plus flumethoxetine, and mesotrione plus S-Methochlor was severe wilt (>50%).

[0350] In summary, all 2,4DC plus S-methoxazolidinone combinations controlled (≥85%) big crabgrass, nightshade, Amaranthus retroflexus, Pennsylvania Polygonum, and Canada thornweed. In many cases, these combinations caused greater than 10% corn wilt. 2,4DC alone only controlled big crabgrass, preferably at rates of 170, 210, and 250, and was safe to corn at all rates. S-methoxazolidinone controlled 6 of the 7 weeds, and it was safe to corn at rates of 534g or lower. The table below highlights the data representing the unexpected synergy of the tested combinations.

[0351] Effects of 2,4-DC+S-methoxazole on -28DAT of Datura stramonium

[0352]

[0353] α – measure of synergy, Y = yes; N = no

[0354] β and ρ - ratio - g ai / ha

[0355] Effect of 2,4-DC+S-methoxazole on -28DAT of Solanum nigrum

[0356]

[0357] α – measure of synergy, Y = yes; N = no

[0358] β and ρ - ratio - g ai / ha

[0359] Effects of 2,4-DC+S-methoxazole on -28DAT of Polygonum pennsylvanicum

[0360]

[0361] α – measure of synergy, Y = yes; N = no

[0362] β and ρ - ratio - g ai / ha

[0363] Effects of 2,4-DC+S-methoxazolidinone on -28DAT of wild buckwheat

[0364]

[0365] α – measure of synergy, Y = yes; N = no

[0366] β and ρ - ratio - g ai / ha

[0367] Example 16: Pre-emergence (PRE) efficacy of a 2,4-DC and Pirovir tank mix.

[0368] In this example, a greenhouse study was conducted to determine the pre-emergence efficacy of a 2,4-DC and Pirovir tank mix (when 2,4-DC or Pirovir was applied at different rates) on weeds selected from the group consisting of giant foxtail (Setariafaberi, SETFA), green foxtail (Setaria virdis, SETVI), golden foxtail (Setariapumila, SETLU), nightshade (Solanum nigrum, SOLNI), kochia (Kochia scoparia, KCHSC), amaranth (Amaranthus retroflexus, AMARE), ragweed (Ambrosiaartemisiifolia, AMBEL), barnyard grass (Echinochloa crus-galli, ECHCG), and giant crabgrass (Digitaria sanguinalis, DIGSA).

[0369] method:

[0370] To determine PRE efficacy, 2,4DC (36.7% CS) at 5 levels, 0, 125, 170, 210, or 250 g ai / ha, and Pirovir (KIH485-85WG) at 5 levels, 0, 50, 65, 80, or 95 g ai / ha, were applied alone or as a tank mix. Additional treatments consisted of Pirovir plus a premix of fluthiacet-methyl (Anthem™ 23.3%) at 169.9 g ai / ha, S-methoxazole (Dual II Magnum, 82.4%) at 1388 g, and mesotrione ( 40%) plus 1252 g of S-methoxazole. An untreated test was included as a reference standard. Treatments were applied pre-emergence on nightshade, giant foxtail, green foxtail, golden foxtail, big crabgrass, Kochia scoparia, Amaranthus retroflexus, ragweed, and barnyard grass.

[0371] Weeds were planted in fiber flats (6"X10") containing Pennington soil and the flats were watered well before application and lightly watered after application. Flats were watered daily and fertilized after treatment application. Each treatment was replicated 3 times. Treatments were applied with compressed air in an orbital spray chamber at 30 GPA using a TeeJet 8001E spray head at 40 PSI. Visible percent weed control data were recorded 14, 21 and 28 days after treatment using a rating of 0 (no control) to 100 (complete plant death). Data (not included) were analyzed using Minitab statistical software with 95% confidence intervals.

[0372] result:

[0373] All 16 combinations controlled (≥85%) Solanum nigrum, Kochia scoparia, Amaranthus retroflexus, Echinochloa crusgalli, Giant crabgrass, Giant foxtail, Green foxtail, and Golden foxtail. Of the 16 combinations, 14 controlled ragweed. 2,4DC alone controlled Kochia scoparia at 210 g ai / ha, Echinochloa crusgalli and Giant crabgrass at 125 g, and Giant foxtail and Green foxtail at 170 g.

[0374] At all rates, Pirovir controlled all weeds except ragweed, which was not controlled at any rate. A premix of Pirovir plus methamphetamine and a tank mix of mesotrione plus S-methoxaline controlled all weeds. S-methoxaline controlled nightshade, redtail amaranth, barnyard grass, giant crabgrass, and all three species of foxtail grass.

[0375] In summary, almost all combinations effectively controlled all weed species (≥ 85% control). 2,4DC alone provided control of Kochia scoparia at 210 g ai / ha, and controlled all grasses except golden foxtail at 170 g.

[0376] All rates of Pirovir controlled all weeds except ragweed. The table below highlights the data representing the unexpected synergy of the tested combinations.

[0377] Effect of 2,4-DC+Pirovec on Ragweed at -28DAT

[0378]

[0379] α – measure of synergy, Y = yes; N = no

[0380] β and ρ - ratio - g ai / ha

[0381] Example 17: Pre-emergence weed efficacy and sugarcane selectivity of a tank-mix combination of 2,4-DC and isoxathiapiprolin.

[0382] In this example, a study was conducted to determine pre-emergence weed efficacy and sugarcane injury when 2,4-DC or isoxathiapiprolin was applied alone or as a tank mix on the following weeds: split-leaf morning glory (Ipomoeahederacea, IPOHE), hairy clover (Bidens pilosa, BIDPI), yellow sedge (Cyperus sculentus, CYPES), big crabgrass (Digitaria sanguinalis, DIGSA) and reverse amaranth (Amaranthus retroflexus, AMARE). The crop tested in this study was sugarcane (var. CTC 20).

[0383] method:

[0384] To determine weed efficacy and sugarcane selectivity: 2,4DC (SC 36%) and isoxathiapiprolin (Balance 20%), applied alone or as a tank mix, at the rates described below. 2,4DC was applied at 500, 750, and 1000 g ai / ha, while isoxathiapiprolin was applied at 80, 100, and 120 g ai / ha. Two commercial standards were included, isoxathiapiprolin ( 3ME, 31.4%), 1120 g ai / ha, and mesotrione ( 40%), 105 g. An untreated test was included as a reference standard. Treatments were applied at PRE to sugarcane (var. CTC 20), morning glory, hairy clover, yellow sedge, crabgrass and amaranth. The weed material was planted in fiber flats (6"X10") containing Pennington soil. The soil was watered before application and lightly watered after application. The flats were watered and fertilized daily after application of the treatment. Treatments were applied with compressed air in an orbital spray chamber at 30 GPA using a TeeJet 8001E nozzle at 40 PSI. Percent weed control and sugarcane injury were recorded 14, 21 and 28 days after treatment (DAT) using a rating of 0 (no control) to 100 (complete plant death). The (not included) data were analyzed using Minitab statistical software with 95% confidence intervals.

[0385] result:

[0386] Tank mix treatments of 2,4DC with isoxaflutole controlled morning glory, hairy clover, big crabgrass, and Amaranthus retroflexus at all rates (≥85% weed control). No tank mix controlled yellow sedge. All tank mixes caused greater than 20% cane whitening. Control of morning glory with 2,4DC alone was achieved at 1000 g, while control of hairy clover with 2,4DC was achieved at 750 g. Crabgrass and Amaranthus retroflexus were controlled with 2,4DC alone at a rate of 500 g or more. Isoxaflutole alone at a rate of 80 g or more controlled hairy clover, big crabgrass, and Amaranthus retroflexus. Isoxaflutole alone caused 26-42% cane whitening at 3 rates. Mesotrione controlled all weeds except morning glory at 105 g. Isoxaflutole controlled hairy clover, big crabgrass, and Amaranthus retroflexus at 1120 g.

[0387] In summary, the tank mix combination of 2,4DC and isoxathiapiprolin controlled all weeds except yellow sedge (≥85% weed control). All 12 tank mix combinations caused >20% whitening of sugarcane at 28 DAT. 2,4DC alone controlled 4 of the 5 species, controlling morning glory, hairy clover, big crabgrass, and redroot. The table below highlights the data representing the unexpected synergy of the tested combinations.

[0388] Effects of 2,4-DC+isoxazone on Pharbouria ovata at -28DAT

[0389]

[0390] α – measure of synergy, Y = yes; N = no

[0391] β and ρ - ratio - g ai / ha

[0392] Example 18: Pre-emergence (PRE) efficacy of a tank-mix combination of 2,4-DC and clomazone.

[0393] In this example, the pre-emergence efficacy of the tank-mix combination of 2,4DC and clomazone when applied at different rates was investigated on the following weeds: bluegrass (Poa annua, POAAN); brome (Bromus secalinus, BROSE); wild oats (Avena fatua, AVEFA); wheatgrass (Elymus repens, AGRRE); field violets (Viola arvensis, VIOAR); blackgrass (Alopecurus myosuroides, ALOMY); Phalaris minor (PHAMI); Apera spica-venti (APESP); golden foxtail (Setaria pumila, SETPU); and goosegrass (Eleusine indica, ELEIN).

[0394] method

[0395] To determine PRE efficacy, 4 rates of 2,4-DC (36.7% CS) and 3 rates of clomazone (Command 3ME, 31.4%) were applied either alone or as a tank mix. 2,4-DC was applied at 0, 125, 170, 210, or 250 g ai / ha and clomazone was applied at 0, 60, 90, or 120 g ai / ha. Additional treatments included application of metazachlor ( 43.1%), 750 g ai / ha, Devrinol 50%), 1260 g, and dimethochlor ( 48%), 1000g ai / ha. Untreated tests were included as reference standards. Treatments were applied immediately after seeding of bluegrass, brome, wild oats, ryegrass, field violets, nigella, small-seeded phragmites, silky wind grass, golden foxtail, and goosegrass. Plants were grown in fiber flats (6"X10") containing Pennington soil, and the flats were well watered before application and lightly watered after application. Flats were watered and fertilized daily after application of treatments. Each treatment was replicated 3 times. Treatments were applied with compressed air in an orbital spray chamber at 30 GPA using a TeeJet 8001E nozzle at 40 PSI. Visible percent weed control was recorded 14, 21, and 28 days after treatment, using a rating of 0 (no control) to 100 (complete plant death). Raw data (not included) were analyzed using Minitab statistical software with 95% confidence intervals.

[0396] result:

[0397] Of the 12 2,4DC and clomazone combinations, none controlled bluegrass, nigella sativa, or small-seeded phalaenopsis (≥85% injury). Three combinations inhibited field violets, thin wheatgrass, and golden foxtail (70-84% injury), and six combinations inhibited silkweed. Five combinations controlled wild oats, 10 combinations controlled bromegrass, and all tank-mix combinations controlled goosegrass.

[0398] When applied alone, 2,4DC controlled goosegrass at ≥170 g ai / ha, while clomazone controlled goosegrass at all rates and bromegrass at 120 g, with no control of other weeds by either herbicide applied alone. Metazachlor controlled all weeds; naproxen controlled all weeds except black cumin. Dimethoate controlled bluegrass, thin wheatgrass, small-seeded phragmites, silky windweed, golden foxtail, and goosegrass.

[0399]

[00136] In summary, 2,4DC alone had good effects on goosegrass. The 2,4DC plus isocyanate combination controlled goosegrass (≥85%). Bromus was controlled synergistically by the tested combinations. While 5 combinations controlled wild oats, the table below provides specific unexpected synergies of the inventive combinations. No combination controlled or inhibited bluegrass, nigella sativa, or phalaenopsis serrata.

[0400] Effects of 2,4-DC+clomazone on Bromus at -28DAT

[0401]

[0402] α – measure of synergy, Y = yes; N = no

[0403] β and ρ - ratio - g ai / ha

[0404] Effects of 2,4-DC+clomazone on -28DAT of wild oats

[0405]

[0406] α – measure of synergy, Y = yes; N = no

[0407] β and ρ - ratio - g ai / ha

[0408] Example 19: Weed efficacy and crop safety of 2,4DC when tank-mixed with diflufenac and PRE-applied.

[0409] In this example, a greenhouse study was conducted to determine the crop selectivity and weed efficacy of 2,4DC alone or in combination with diflufenicol at various rates of pre-emergence (PRE) application on the following weeds: multiflora ryegrass (Lolium perenne L.ssp.multiflorum, LOLMU); corn poppy (Papaver rhoeas, PAPRH); wild oats (Avena fatua, AVEFA); bluegrass (Poa annua, POAAN); wheatgrass (Elymus repens, AGRRE); brome (Bromus secalinus, BROSE). In this study, the crops tested included wheat, barley and oilseed rape (OSR).

[0410] method:

[0411] To determine weed efficacy and wheat, barley, or OSR selectivity: 2,4DC (SC 36.7%) and diflufenicol (CS 19.5%) were applied preemergence, either alone or as a tank mix, at the rates described below. 2,4DC was applied at 125, 170, and 250 g ai / ha, while diflufenicol was applied at 50, 75, and 100 g ai / ha. Pyroxasulfone (KIH-485, 85%) was applied at 74.3 g ai / ha, and Prowl EC, 37.4%), 1,200 g ai / ha, or a premix of chlorsulfuron plus metsulfuron-methyl (Report Extra, 75%), 15.8 g ai / ha, as commercial standards. Untreated tests were included as reference standards.

[0412] All plants were planted directly in 6x10" fiber flats with Pennington soil. 2,4DC and diflufenicol were applied individually or in combination as tank mixes at the rates described below. Herbicides included as standards for comparison were pyrosulfuron, pendimethalin, and a premix of chlorsulfuron plus metsulfuron-methyl, all applied at the rates shown above. Treatments were replicated 3 times. Flats were watered after seeding but before treatment. After application, flats were placed in the greenhouse and lightly watered. Flats were then watered and fertilized daily. Treatments were applied with compressed air at 30 GPA in an orbital spray chamber using a TeeJet 8001E spray head at 40 PSI. Visible percent weed control and crop safety were recorded 14, 21, and 28 days after treatment (DAT) using a rating of 0 (no control / no damage) to 100 (total plant death). Data (not included) were analyzed with Minitab statistical software with 95% confidence intervals.

[0413] result:

[0414] 2,4DC (36.7% CS) applied at 125 g ai / ha provided suppression of corn poppy (70-84% injury), with higher rates controlling corn poppy (≥85% injury). No other weeds were controlled by any of the 2,4DC applied alone in this evaluation. Wheat, barley, and rapeseed (OSR) were safe (≤10% injury) for all individual treatments of 2,4DC. 2,4DC plus fluazifop as a tank mix controlled field violets in all combinations, 11 of the 12 combinations controlled corn poppy, 7 combinations controlled bluegrass, and 6 combinations controlled multiflora ryegrass. All combinations were safe for barley; only one tank mix combination moderately injured wheat (12%), while all combinations of 2,4DC plus fluazifop injured OSR.

[0415] The herbicide standards tested for comparative efficacy and safety included: 74.3 g of Pirowei, which controlled all weeds except field violets and was safe only to wheat; 1200 g of pendimethalin applied controlled corn poppies and field violets and was safe to barley; and a premix of chlorsulfuron plus methylsulfuron-methyl (Report Extra) at 15.8 g also controlled corn poppies and field violets and provided selectivity to wheat.

[0416] In summary, 2,4DC applied alone, controlled corn poppy when applied at ≥170 g ai / ha, and was safe for all crops at all rates. Most combinations of 2,4DC plus diflufenicol controlled corn poppy and bluegrass, and all combinations controlled field violets. Most combinations of 2,4DC plus diflufenicol controlled multiflorus ryegrass when 2,4DC was applied at ≥210 g. Barley was not injured by any combination, while wheat was only moderately injured by one combination (12%); canola was injured by all tank-mix combinations of 2,4DC plus diflufenicol. The table below highlights the data analysis that represents the unexpected synergy of the tested combinations.

[0417] Effects of 2,4-DC+pyrifos on Lolium multiflorum at -28DAT

[0418]

[0419] α – measure of synergy, Y = yes; N = no

[0420] β-ratio-g ai / ha

[0421] Effects of 2,4-DC+pyrifos on bluegrass at -28DAT

[0422]

[0423] α – measure of synergy, Y = yes; N = no

[0424] β and ρ - ratio - g ai / ha

[0425] Example 20: Pre-emergence (PRE) weed efficacy of 2,4DC plus dimethoate-P.

[0426] In this example, a greenhouse study was conducted to determine the weed efficacy of 2,4DC when applied as a PRE, alone at various rates, or in combination with dimethoate-P as a pre-emergence treatment on the following weeds: Chenopodium album (CHEAL); Cirsium arvense (CIRAR); Sinapis arvensis (SINAR); Shepherd's purse (CAPBU); Amaranthus retroflexus (AMARE); Nigella sativa (Alopecurus myosuroides (ALOMY); Setaria faberi (SETFA); Eleusine indica (ELEIN); and Stellaria media (STEME).

[0427] Material:

[0428] herbicide

[0429] 2,4-DC-21 (36.7% CS): 125, 170, 210 or 250 g ai / ha applied alone or as a tank mix with dimethoate-P.

[0430] Dimethoate-P (Outlook, 63.9%): 250, 375, 500 g ai / ha, combined with 2,4DC and alone, additionally treated alone at 750 g ai / ha.

[0431] Butisan (43.1%): 500 g ai / ha

[0432] Weeds:

[0433] Quinoa

[0434] field thistle

[0435] Wild mustard

[0436] Shepherd's Purse

[0437] Amaranthus retroflexus

[0438] Nigella sativa

[0439] giant foxtail

[0440] Goosegrass

[0441] Chickweed

[0442] method:

[0443] All plants were planted directly in 6x10" fiber flats using Pennington soil. 2,4DC and dimethazone-P were applied individually or in tank mix combinations at the rates described below. The herbicide included as a standard for comparison was metazachlor plus dimethazone-P (500 g) as a tank mix combination. An untreated test was included as a reference standard. Treatments were replicated 3 times. Flats were watered after seeding but before treatment. After application, flats were placed in the greenhouse and lightly watered. Flats were then watered and fertilized daily. Treatments were applied with compressed air in an orbital spray chamber at 30 GPA using a TeeJet 8001E spray head at 40 PSI. Percent visible weed control was recorded 14, 21 and 28 days after treatment (DAT) using a rating of 0 (no control) to 100 (total plant death). Data were analyzed using Minitab statistical software with 95% confidence intervals.

[0444] result:

[0445] 2,4DC (36.7% CS) applied alone at 125 g ai / ha controlled thistle, giant foxtail, goosegrass, and chickweed (≥85% injury); and shepherd's purse was also controlled by 2,4DC at 210 g. All tank-mix combinations of 2,4DC plus thiamethoxam-P controlled thistle, giant foxtail, goosegrass, chickweed, shepherd's purse, and redleaf amarant. When 2,4DC was applied as a tank-mix of 250 g with any rate of thiamethoxam-P, it controlled or inhibited (70-84% injury) pigweed. Four tank-mix combinations inhibited wild mustard; one combination inhibited black cumin. Dimethiamethoxam-P alone controlled redleaf amarant, giant foxtail, and goosegrass at all rates; controlled chickweed at ≥375 g; controlled shepherd's purse at ≥500 g; and controlled thistle at 750 g. Chenopodium album or wild mustard were suppressed by some rates of dimethazone-P alone, and Nigella sativa was not controlled or suppressed at any rate of dimethazone-P alone. A combination comprising 500 g of metazachlor plus 500 g of dimethazone-P for comparison controlled all the tested weeds except wild mustard.

[0446] In summary, 2,4DC applied alone controlled thistle, giant foxtail, goosegrass, and chickweed at all rates and controlled shepherd's purse at ≥210 g ai / ha. 2,4DC tank mixes with fenacet-P controlled all of the aforementioned weeds as well as Amaranthus retroflexus in all cases; some combinations controlled Chenopodium album when 2,4DC was applied at 250 g.

[0447] The table below highlights the unexpected synergies of the test combinations.

[0448] Effects of 2,4-DC+dimethathiachlor-P on -28DAT of Chenopodium album

[0449]

[0450] α – measure of synergy, Y = yes; N = no

[0451] β and ρ - ratio - g ai / ha

[0452] Effects of 2,4-DC+dimethathiachlor-P on -28DAT of Shepherd's Purse

[0453]

[0454] α – measure of synergy, Y = yes; N = no

[0455] β and ρ - ratio - g ai / ha

[0456] Example 21: Pre-emergence (PRE) weed efficacy of 2,4DC against European weeds when mixed with S-methoxazole tank mix.

[0457] In this example, a greenhouse study was conducted to determine the weed efficacy of 2,4DC at various rates when applied alone or as a tank mix with S-methoxazole on the following weeds: Elymus repens (AGREE), Stellaria media (STEME); Hemp (Abutilon theophrasti, ABUTH); Golden foxtail (Setaria pumila, SETLU); Green foxtail (Setaria viridis, SETVI); Chenopodium album (CHEAL); Barnyard grass (Echinochloa crus-galli, ECHCG).

[0458] method:

[0459] 2,4-DC (36.7% CS) was applied as a PRE at 0, 125, 170, 210, or 250 g ai / ha, or as a PE with S-methoxazole (Dual II 82.4%) tank mix was applied as a PRE at 0, 267, 534, 801, or 1070 g ai / ha. TM , 23.3%) was applied at 169.9 g ai / ha, mesotrione ( 40%), 123 g, plus S-methoxazole (Dual II 82.4%), 1252g, of a tank mix was used as a standard for comparison. Elytium, chickweed, hemp, golden foxtail, green foxtail, quinoa, and barnyard grass were sown directly into 6"x10" fiber flats using Pennington soil. The flats were watered after sowing but before treatment. After application, the flats were placed in a greenhouse and lightly watered. Afterwards, the flats were watered and fertilized daily. Each treatment was repeated 3 times. Treatment was performed with compressed air in an orbital atomization chamber at 40psi and 30GPA spray volume, using a TeeJet 8001E nozzle. Visible percentage weed control was recorded at 14, 21, and 28 days after treatment (DAT). Weed control was evaluated using a rating of 0 (no control) to 100 (complete plant death). The (not included) data were analyzed using Minitab statistical software with a 95% confidence interval.

[0460] Results for 28DAT:

[0461] 2,4DC applied alone controlled chickweed (≥85% injury) at all rates, barnyard grass at ≥210 g ai / ha, and green foxtail at 250 g. S-Methiochlor applied alone controlled golden foxtail, green foxtail, and barnyard grass at all rates, controlled either Elymus or chickweed at ≥534 g, and Chenopodium album at ≥801 g. All 16 encapsulated tank mixes of 2,4DC plus S-Methiochlor controlled chickweed, golden foxtail, green foxtail, and barnyard grass. Ten tank mix combinations controlled Elymus; the other six combinations provided Elymus suppression (control ranged from 70-84%).

[0462] Thirteen combinations of 2,4DC plus S-methoxazole controlled Chenopodium album, two combinations had suppression, and one combination had no control. None of the treatments containing 2,4DC or S-methoxazole (either alone or in combination) controlled or suppressed Hemp. In this study, two standard tests, a premix of fluazifop-methyl plus pyraclostrobin (Anthem), or a tank mix of mesotrione plus S-methoxazole, controlled all weeds.

[0463] In summary, 2,4DC applied alone controlled chickweed at all rates, barnyard grass and green foxtail at some rates, and 2,4DC applied alone did not control other weeds at any rate. S-Methiochlor controlled golden foxtail, green foxtail, and barnyard grass at all rates; and controlled thin wheatgrass, chickweed, and pigweed at some rates. All tank-mix combinations of 2,4DC plus S-Methiochlor controlled chickweed, golden foxtail, green foxtail, and barnyard grass; most combinations controlled pigweed and thin wheatgrass. The table below highlights the unexpected synergy of the tested combinations.

[0464] Effects of 2,4-DC+S-methoxazole on Chenopodium album at 28DAT

[0465]

[0466] α – measure of synergy, Y = yes; N = no

[0467] β and ρ - ratio - g ai / ha

[0468] Example 22: Weed efficacy of 2,4DC when tank-mixed with S-methoxazole against a Brazilian weed spectrum at the pre-emergence (PRE) stage.

[0469] In this example, a greenhouse study was conducted to determine the weed efficacy of 2,4DC when applied alone at various rates or as a tank mix with S-methoxazole at different rates in a pre-emergence manner on the following weeds: Sorghum halepense (SORHA); wild mustard (Sinapis arvensis, SINAR); bamboo leaf vegetable (Commelina benghalensis, COMBE); Sida spinosa (SIDSP); hairy clover (Bidens pilosa, BIDPI); morning glory (Ipomoea spp.IPO sp); Chenopodium album (CHEAL); Eleusine indica (ELEIN).

[0470] Materials and methods

[0471] 2,4-DC (36.7% CS) was applied as a PRE at 0, 125, 170, 210, or 250 g ai / ha, or as a PE with S-methoxazole (Dual II 82.4%) tank mix was applied as a PRE at 0, 267, 534, 801, or 1070 g ai / ha. TM , 23.3%) was applied at 169.9 g ai / ha, mesotrione ( 40%), 123 g, plus S-methoxazole (Dual II 82.4%), 1252g, of a tank mix was used as a standard for comparison. Sorghum chinense, wild mustard, bamboo leaf vegetable, spiny yellow flower, hairy clover, morning glory, quinoa and goosegrass were sown directly into 6"x10" fiber flats using Pennington soil. The flats were watered after sowing but before treatment. After application, the flats were placed in a greenhouse and lightly watered.

[0472] Afterwards, the plates were watered and fertilized daily. Each treatment was replicated 3 times. Treatments were applied with compressed air in an orbital atomization chamber at 40 psi and 30 GPA spray volume using a TeeJet 8001E nozzle. Visible percent weed control was recorded at 14, 21, and 28 days after treatment (DAT). Weed control was assessed using a rating of 0 (no control) to 100 (complete plant death). Data were analyzed using Minitab statistical software with 95% confidence intervals.

[0473] Results for 28DAT:

[0474] 2,4DC applied alone controlled Sorghum chinense (≥85% injury) at 210 g ai / ha, Chenopodium album at 250 g, and Goosegrass at all rates. All combinations of 2,4DC plus S-methoxychlor as a tank mix controlled Sorghum chinense, Chenopodium album, and Goosegrass, and 13 of the 16 combinations controlled bamboo shoots (the other 3 combinations provided 70-84% control). 11 combinations had comparable control of Achyranthes spinulosa, while 3 combinations provided control. 5 combinations controlled hairy clover, and no combinations controlled wild mustard or morning glory. S-methoxychlor applied alone controlled Sorghum chinense and Goosegrass at all rates, and controlled bamboo shoots, Achyranthes spinulosa, and Chenopodium album at 801 g. Mesotrione plus S-methoprim as a tank mix controlled all weeds, and a premix of fluthiazide plus pyraclostrobin controlled all weeds except hairy clover.

[0475] In summary, 2,4DC applied alone controlled goosegrass at all rates, sorghum chinense and goosegrass at some rates, and 2,4DC alone did not control other weeds. S-Methiochlorant alone controlled goosegrass and sorghum chinense at all rates, and controlled bamboo shoots, goldenrod, and goosegrass at some rates. All tank-mix combinations controlled goosegrass, goldenrod, and goosegrass; most controlled bamboo shoots, while some combinations controlled goldenrod and hairy clover. None of the treatments containing 2,4DC or S-Methiochlorant controlled wild mustard and morning glory. The table below highlights the unexpected synergy of the tested combinations.

[0476] Effects of 2,4-DC+S-methoxazolidinone on -28DAT of Bamboo Leaf Vegetable

[0477]

[0478] α – measure of synergy, Y = yes; N = no

[0479] β and ρ - ratio - g ai / ha

[0480] Effects of 2,4-DC+S-methoxazole on Trifolium repens at 28 DAT

[0481]

[0482] α – measure of synergy, Y = yes; N = no

[0483] β and ρ - ratio - g ai / ha

[0484] Example 23: Weed efficacy and sugarcane selectivity when 2,4DC plus sulfentrazone are applied pre-emergence (PRE) as a tank mix.

[0485] In this example, a greenhouse study was conducted to determine the weed efficacy and sugarcane selectivity of 2,4-DC when applied at various rates as a PRE alone or in combination with sulfentrazone as a tank mix on the following weeds: Digitaria sanguinalis (DIGSA); Amaranthus retroflexus (AMARE); Cyperus esculentus (CYPES); Hairy clover (Biden pilosa, BIDPI); Morning glory (Ipomoea spp.). The crop tested in this study was sugarcane (CTC 20).

[0486] Material:

[0487] herbicide

[0488] 2,4-DC (36% CS): 500, 750, or 1,000 g ai / ha applied alone or as a tank mix with sulfentrazone.

[0489] Spartan 4F (39.6%): 210, 315, or 420 g ai / ha applied alone or in combination with 2,4DC.

[0490] Isotrione (Balance Flexx, 20%): 85 g ai / ha

[0491] Mesotrione (Callisto, 40%): 105 g ai / ha

[0492] Clomazone (Command 3ME, 31.4%): 1120 g ai / ha

[0493] Weeds:

[0494] Big horse angelica

[0495] Yellow sedge

[0496] Amaranthus retroflexus

[0497] Hairy Clover

[0498] Morning glory

[0499] crop:

[0500] Sugarcane (CT20)

[0501] method:

[0502] All weeds were planted directly into 6x10" fiber flats with Pennington soil. Sugarcane was sown directly into 6" plastic pots with 3-4" cane stem segments, sprouted upward, and bud shade removed. 2,4DC and sulfentrazone were applied alone or in a tank mix at the rates described below. Herbicides included as control standards were isoxaflutole, mesotrione, and clomazone. Treatments were replicated 3 times. Flats were watered after sowing but before treatment. After application, flats were placed in the greenhouse and lightly watered. Flats were then watered and fertilized daily. Treatments were applied with compressed air at 30 GPA in an orbital spray chamber using a TeeJet 40 PSI. 8001E sprinkler. Visible percent weed control was recorded 14, 21 and 28 days after treatment (DAT) using a rating scale of 0 (no control) to 100 (total plant death). Visible percent sugarcane injury was recorded at 21 and 28 DAT using a rating scale of 0 (no injury, blanching, wilting or necrosis observed) to 100 (total plant death). Data were analyzed using Minitab statistical software with 95% confidence intervals.

[0503] Results for 28DAT:

[0504] 2,4DC (36% SC) applied alone at ≥500 g ai / ha controlled big crabgrass and Amaranthus retroflexus (≥85% injury). 2,4DC at 1000 g inhibited hairy clover and morning glory (70-84% injury). All tank-mix combinations of 2,4DC plus sulfentrazone controlled big crabgrass, yellow sedge, Amaranthus retroflexus, hairy clover, and morning glory. Sulfentrazone alone controlled hairy clover at 315 g; all rates of sulfentrazone controlled all other weeds. Mesotrione at 105 g controlled all weeds except morning glory, and isoxaflutole at 85 g or 1120 g controlled big crabgrass, Amaranthus retroflexus, and hairy clover. In this evaluation, sugarcane was safe (≤10% injury) in all treatments except isoxaflutole, which caused 12% injury.

[0505] The combination of 2,4DC plus sulfentrazone provides good efficacy against all weeds while maintaining crop selectivity. Other crop segments should be explored for their weed spectrum and crop selectivity for these two herbicides.

[0506] In summary, all rates of 2,4DC-4SC applied alone controlled crabgrass and Amaranthus retroflexus. All tank-mix combinations of 2,4DC with sulfentrazone controlled all weeds evaluated. All applications of 2,4DC or sulfentrazone, alone or in combination, were safe for sugarcane. The table below highlights the unexpected synergy of the tested combinations.

[0507] Effects of 2,4-DC+sulfentrazone on -28DAT of Trifolium repens

[0508]

[0509] α – measure of synergy, Y = yes; N = no

[0510] β and ρ - ratio - g ai / ha

[0511] Example 24: PRE efficacy of a tank mix combination of 2,4-DC and Pirovi.

[0512] In this example, a greenhouse study was conducted to determine the pre-emergence (PRE) efficacy of a 2,4-DC and Pirovir tank mix (when 2,4-DC or Pirovir was applied at different rates). The weeds tested included: Setaria faberi (SETFA), Setaria virdis (SETVI), Setaria pumila (SETLU), Solanum nigrum (SOLNI), Kochia scoparia (KCHSC), Amaranthus retroflexus (AMARE), Ambrosia artemisiifolia (AMBEL), Echinochloa crus-galli (ECCHCG), Digitaria sanguinalis (DIGSA).

[0513] Materials and methods

[0514] To determine PRE efficacy, 2,4DC-21 (36.7% CS) was applied alone or as a tank mix at 5 levels, 0, 125, 170, 210, or 250 g ai / ha, and Pirovir (KIH485-85WG) was applied at 5 levels, 0, 50, 65, 80, or 95 g ai / ha. Additional treatments consisted of Pirovir plus a premix of fluthiacet-methyl (Anthem™ 23.3%) at 169.9 g ai / ha, S-Methocarb (Dual II 82.4%), and 123 g of mesotrione ( 40%) plus 1252 g of S-methoxal. An untreated test was included as a reference standard. Treatments were applied pre-emergence on nightshade, giant foxtail, green foxtail, golden foxtail, big crabgrass, Kochia scoparia, Amaranthus retroflexus, ragweed, and barnyard grass. Weeds were grown in fiber flats (6"X10") containing Pennington soil and the flats were watered well before application and lightly watered after application. Flats were watered and fertilized daily after application of treatments. Each treatment was replicated 3 times. Treatments were applied with compressed air in an orbital spray chamber at 30 GPA using a TeeJet 8001E spray head at 40 PSI. Visible percent weed control data were recorded 14, 21, and 28 days after treatment using a rating of 0 (no control) to 100 (complete plant death). Data (not included) were analyzed using Minitab statistical software with 95% confidence intervals.

[0515] result:

[0516] All 16 combinations controlled (≥85%) nightshade, kochia, amaranth retroflexus, barnyard grass, big crabgrass, giant foxtail, green foxtail, and golden foxtail. Of the 16 combinations, 14 controlled ragweed. 2,4DC alone controlled kochia at 210 g ai / ha, barnyard grass and big crabgrass at 125 g, and big foxtail and green foxtail at 170 g. Regardless of the rate, Piroway controlled all weeds except ragweed, which was not controlled at any rate. Premixes of Piroway plus methamphetamine and tank mixes of mesotrione plus S-methoxychlor controlled all weeds. S-methoxychlor controlled nightshade, amaranth retroflexus, barnyard grass, big crabgrass, and all three types of foxtail.

[0517] In summary, almost all combinations effectively controlled all weeds (≥ 85% control). 2,4DC alone provided control of Kochia scoparia at 210 g ai / ha, and controlled all grasses except golden foxtail at 170 g. Pirowei controlled all weeds except ragweed at all rates. The table below highlights the data analyzing the unexpected synergy of the tested combinations.

[0518] Effects of 2,4-DC+Pirovec on -28DAT of Potato

[0519]

[0520] α – measure of synergy, Y = yes; N = no

[0521] β and ρ - ratio - g ai / ha

[0522] Effect of 2,4-DC+Pirovec on the PRE of Sorghum bicolor at -28DAT

[0523]

[0524] α – measure of synergy, Y = yes; N = no

[0525] β and ρ - ratio - g ai / ha

[0526] Effects of 2,4-DC+Pirovec on -28DAT of Elytium spp.

[0527]

[0528] α – measure of synergy, Y = yes; N = no

[0529] β and ρ - ratio - g ai / ha

[0530] Example 25: Pre-emergence (PRE) weed efficacy and crop selectivity of 2,4DC when tank mixed with Pirovir.

[0531] In this example, a greenhouse study was conducted to determine the weed efficacy and crop selectivity of 2,4DC applied alone at various rates or as a tank mix with Pirovir in a PRE regime on the following weeds: Datura (Datura stramonium, DATST); Poinsettia (Euphorbia heterophylla, EUHL), Hairy Clover (Bidens pilosa, BIDIPI); Nightshade (Solanum nigrum, SOLNI). The crop tested in this study was corn.

[0532] Materials and methods

[0533] 2,4-DC (36.7% CS) was applied as a PRE at 0, 125, 170, 210, or 250 g ai / ha, or as a tank mix with Pirovir (KIH-485, 85% WP) at 0, 50, 65, 80, or 95 g ai / ha as a PRE. TM , 23.3%) at 169.9 g ai / ha, S-methoxazole (Dual II 82.4%) was applied at 1389 g, and 123 g of mesotrione ( 40%) plus 1252g of S-methoxytoxin (Dual II 82.4%), as a standard for comparison. An untreated test was included as a reference standard. Datura, Poinsettia, Hairy Clover, Solanum nigrum, and Corn were seeded directly into 6"x10" fiber flats using Pennington soil. Flats were watered after seeding but before treatment. After application, flats were placed in a greenhouse and lightly watered. Flats were then watered and fertilized daily. Treatments were applied with compressed air in an orbital spray chamber at 40 psi and 30 GPA spray volume using a TeeJet 8001E spray head. Visible percent weed control and crop injury data were recorded at 14, 21, and 28 days after treatment (DAT). Weed control was evaluated using a rating of 0 (no control) to 100 (total plant death). Crop injury: blanching, wilt, and necrosis were evaluated using a rating of 0 (no injury) to 100 (total plant death). Data (not included) were analyzed using Minitab statistical software with 95% confidence intervals.

[0534] result:

[0535] 2,4DC applied alone controlled Solanum nigrum (≥85% injury) at 170 g ai / ha, provided no control of other test weeds when applied alone at any rate, and was safe to corn at all rates. 2,4DC plus Pirovir controlled Solanum nigrum for all tank-mix combinations, controlled Datura stramonium for all but one combination, controlled Poinsettia ovata for two combinations, and controlled Hairy Clover for one combination. No tank-mix combination caused blanching injury (≥10%) to corn, seven combinations caused moderate (11-20%) wilt to corn, and three combinations caused severe wilt (≥20%) to corn. No tank-mix combination of 2,4DC plus Pirovir caused greater than 10% necrosis. When total combined injury (percent blanching + percent wilt + percent necrosis) was considered, only one tank-mix combination was safe to corn; five combinations were moderately safe, and ten combinations caused severe injury to corn. Fluthiazide plus pyraclostrobin controlled Datura and Solanum nigrum and caused severe wilt in corn. S-Methochlor controlled only Solanum nigrum and also caused severe wilt in corn. Mesotrione plus S-Methochlor controlled all weeds tested and caused moderate wilt in corn.

[0536] In summary, 2,4DC applied alone controlled nightshade at most rates, and 2,4DC alone did not control other weeds. 2,4DC plus Pirovir controlled nightshade for all applications, most combinations controlled Datura, and some tank mix applications controlled Poinsettia or Hairy Clover. 2,4DC alone was safe for corn at all rates, and tank mixes of 2,4DC plus Pirovir injured corn for most applications. The table below highlights the data for the unexpected synergy of the tested combinations.

[0537] Effect of 2,4-DC+Pirovec on -28DAT of Datura

[0538]

[0539] α – measure of synergy, Y = yes; N = no

[0540] β and ρ - ratio - g ai / ha

[0541] Effect of 2,4-DC+Pirovec on the PRE-28DAT of wild chimpanzee

[0542]

[0543] α – measure of synergy, Y = yes; N = no

[0544] β and ρ - ratio - g ai / ha

[0545] Effect of 2,4-DC+Pirovec on -28DAT of Trifolium pubescens

[0546]

[0547] α – measure of synergy, Y = yes; N = no

[0548] β and ρ - ratio - g ai / ha

[0549] Example 26: Pre-emergence (PRE) efficacy of 2,4-DC and sulfentrazone combination on sedge.

[0550] In this example, a greenhouse study was conducted to determine sedge control of the following weeds: Cyperus esculentus (CYPES), Cyperus rotundus (CIPRO), and Commelina benghalensis (COMBE) when 2,4DC or sulfentrazone was applied alone or in combination.

[0551] Materials and methods

[0552] To evaluate the effects of 2,4DC (36% SC) and Spartan 39.6%) on sedges, 2,4DC was applied at 50, 100, or 200 g ai / ha as a tank mix with 105, 210, or 315 g ai / ha of sulfentrazone. Each herbicide was applied alone at the given rate, as well as 2,4DC alone at 400 g and clomazone (Command 31.4%) at 100 g plus sulfentrazone at 315 g as an additional treatment. An untreated test was included as a reference standard. Treatments were applied when growing yellow sedge, cyperus and bamboo shoots. Plants were grown in fiber flats containing Pennington soil and the flats were well watered before application and lightly watered after application. Flats were watered and fertilized daily after application of treatments. Treatments were applied with compressed air in an orbital spray chamber at 30 GPA using a TeeJet 8001E nozzle at 40 PSI. Visible percent weed control was recorded 14, 21 and 28 days after treatment (DAT) using a rating of 0 (no control) to 100 (complete plant death). Data (not included) were analyzed using Minitab statistical software with 95% confidence intervals.

[0553] result:

[0554] When 2,4DC and sulfentrazone were applied together, 7 of the 9 tank-mix combinations provided control of yellow sedge at 28 DAT. 2,4DC applied at all rates and sulfentrazone applied at 315 g provided control of cyperus rotundus. In most cases, the combinations controlled cyperus rotundus when sulfentrazone was applied at 210 or 315 g.

[0555] 2,4DC alone provided no control of sedges at any rate, except for 400 g which provided control of sedge. Sulfentrazone alone controlled yellow sedge at all rates, sedge at 210 or 315 g, and did not control cyperus at any rate. The combination of clomazone and sulfentrazone controlled all three sedges at 28 DAT.

[0556] In summary, the combination of 2,4DC plus sulfentrazone controlled yellow sedge in most cases, while only 3 combinations controlled Cyperus rotundus. Control of bamboo shoots was observed for the tank mix combination when sulfentrazone was applied at 315 g ai / ha. 2,4DC alone provided control of bamboo shoots only at 400 g. The table below highlights the unexpected synergistic effect of the tested combinations on Cyperus rotundus.

[0557] Effects of 2,4-DC+sulfentrazone on -28DAT of PRE in Cyperus rotundus

[0558]

[0559] α – measure of synergy, Y = yes; N = no

[0560] β and ρ - ratio - g ai / ha

[0561] Example 27: Weed efficacy / crop selectivity of tank-mixed formulations of 2,4DC and metazachlor.

[0562] In this example, a greenhouse study was conducted to determine the pre-emergence (PRE) weed efficacy / crop selectivity of 2,4DC with metazachlor. The weeds tested in this study were multiflora ryegrass (Lolium perenne.multiflorum, LOLMU), wild mustard (Sinapis arvensis, SINAR), bluegrass (Poa annuaPOAAN), wild oats (Avena fatua, AVEFA), blackgrass (Alopecurus myosuroides, ALOMY), quinoa (Chenopodium albumCHEAL), Phalaris minor (PHAMI), chickweed (Stellaria media, STEME), poppy (Papaver rhoeas, PAPRH) and the crops tested were wheat and rapeseed.

[0563] Materials and methods

[0564] To determine PRE weed efficacy and crop selectivity, 2,4DC (36% SC) was applied alone at 31.25, 62.5, 125, 250, or 375 g or in combination with metazachlor ( S 43.1%) were applied at 250, 500, and 750 g ai / ha. Other treatments included metazachlor alone, a tank mix combination of isochloramine plus metazachlor 250+750 g at the rates described above, and a premix of isochloramine plus metazachlor at 100 g ai / ha. Treatments were applied before germination of multiflora ryegrass, wild oats, black cumin, small-seeded phragmites, chickweed, pigweed, corn poppy, wild mustard, bluegrass, canola, and wheat. Plants were grown in fiber flats (6"X10") containing Pennington soil, and the flats were well watered before application and lightly watered after application. Flats were watered and fertilized daily after application of the treatments. Treatments were applied with compressed air in an orbital spray chamber at 30 GPA using a TeeJet 8001E nozzle at 40 PSI. Visible percent weed control and visible percent crop injury data were recorded 14, 21 and 28 days after treatment using a rating scale of 0 (no control / no injury) to 100 (total plant death). Data (not included) were analyzed using Minitab statistical software with 95% confidence intervals. Ratings were performed only on wheat and poppy at 14 and 21 DAT.

[0565] result:

[0566] In this study, 2,4DC provided good control of black cumin at 375g when given alone; provided control of multifloral ryegrass at ≥125g, and provided control of chickweed at all rates. Metazachlor alone controlled black cumin at 750g, and also controlled bluegrass, multifloral ryegrass, quinoa, small-seeded phragmites, and chickweed at all rates. When given together, all 15 combinations of 2,4DC combined with metazachlor controlled corn poppy, bluegrass, multifloral ryegrass, quinoa, small-seeded phragmites, and chickweed. Among the 15 combinations, wild oats and black cumin were controlled in 6 and 8 combinations, respectively. All combinations caused severe damage to wheat (>60%) at 21DAT, and severe damage to rapeseed at 28DAT. No combination obtained control of wild mustard.

[0567] Clomazone and metazachlor (tank mix) controlled bluegrass, multiflora ryegrass, pigweed, quinoa, and chickweed. However, clomazone and metazachlor (premix) controlled bluegrass, multiflora ryegrass, pigweed, quinoa, and chickweed.

[0568] In summary, all combinations of 2,4DC with metazachlor completely controlled corn poppy, bluegrass, multiflora ryegrass, pigweed, small-seeded phragmites, and chickweed at 28 DAT. Note that nearly half of the combinations controlled wild oats and nigella. All combinations caused high injury to wheat at 21 DAT, and high injury to canola at 28 DAT. 2,4DC alone had control of chickweed at all rates, control of multiflora ryegrass at 125 g, and control of nigella at 375 g.

[0569] The table below highlights the unexpected synergies of the test combinations.

[0570] Effects of 2,4-DC+pyraclostrobin on -28DAT of wild oats

[0571]

[0572] α – measure of synergy, Y = yes; N = no

[0573] β and ρ - ratio - g ai / ha

[0574] Effect of 2,4-DC+metachlor on PRE of Nigella sativa at 28DAT

[0575]

[0576] α – measure of synergy, Y = yes; N = no

[0577] β and ρ - ratio - g ai / ha

[0578] Example 28: Pre-emergence (PRE) weed efficacy / crop selectivity of a tank-mix combination of 2,4DC and metazachlor plus naproxil.

[0579] In this example, a greenhouse study was conducted to determine weed efficacy / crop selectivity when the herbicides 2,4-DC or metazachlor plus naproxen were applied alone or combined in a three-component formulation. The weeds tested in the study were Amaranth retroflexus (AMARE), Lolium perenne multiflorum (LOLMU), Sinapis arvensis (SINAR), Poa annua (POAAN), Avena fatua (AVEFA), Nigella sativa (ALOMY), Chenopodium albumCHEAL, Phalaris minor (PHAMI), Stellaria media (STEME), Papaver rhoeas (PAPRH) and Apera spica-venti (APESV). The crops tested were wheat and rapeseed.

[0580] Materials and methods

[0581] To determine the efficacy and crop selectivity of 2,4DC or its potential tank mix combinations, 2,4DC or metazachlor plus naproxen were applied alone or in a three-component combination at the following rates: 2,4DC (36% SC) at 50, 100, or 200 g ai / ha; metazachlor (43.1% S) was 250, 500, or 750 g ai / ha; and naproxenamide ( 50DF) at 315 g ai / ha. In addition, 2,4DC was applied alone at 400 g ai / ha. Other treatments included clomazone (Command A tank mix of clomazone (31.4%) plus metazachlor plus naproxil, 100+750+315 g ai / ha, and a premix of clomazone (2.13%) plus metazachlor (13%) plus naproxil (13.6%), 1572 g ai / ha were applied. An untreated test was included as a reference standard.

[0582] Treatments were applied prior to germination of Amaranthus retroflexus, Lolium multiflorum, Wild oats, Nigella cumin, Phragmites australis, Chickweed, Pigweed, Corn Poppy, Wild Mustard, Bluegrass, Silkweed, Canola, and Wheat. Plants were grown in fiber flats (6"X10") containing Pennington soil and the flats were watered well prior to application and lightly after application. Flats were watered and fertilized daily after application of treatments. Treatments were applied with compressed air in an orbital spray chamber at 30 GPA using a TeeJet 8001E spray head at 40 PSI. Visible percent weed control and visible percent crop injury data were recorded 14, 21, and 28 days after treatment using a rating scale of 0 (no control / no injury) to 100 (total plant death). Data (not included) were analyzed using Minitab statistical software with 95% confidence intervals.

[0583] Results for 28DAT:

[0584] All three-component combinations of 2,4DC / metachlor / napropamide provided good control of Amaranthus retroflexus, Corn Poppy, Lolium multiflorum, Bluegrass, Wild Oats, Pigweed, Phalaenopsis spp., Chickweed, and Silkweed. Eight combinations controlled Nigella cumin. No combination was safe for wheat and canola.

[0585] 2,4DC alone provided control of Amaranthus retroflexus and Corn Poppy at 400g, control of Lolium multiflorum at ≥200g, control of Nigella cumin and Chenopodium album at 400g, and control of Chickweed at all rates. 2,4DC caused greater than 10% injury to oilseed rape at all rates, and 2,4DC was safe in wheat up to 200g ai / ha.

[0586] All combinations of metazachlor plus naproxil provided control for all species at almost all rates, except for metazachlor ≤ 500 g and naproxil at 315 g for wild mustard and the lowest rate of the combination for wild oats and black cumin. No combination was safe for oilseed rape and wheat.

[0587] The three-component approach of clomazone / metachlor / napropamide (tank mix / premix) provided control of all species, except for wild mustard and nigella, where the premix did not control. Both the tank mix and premix caused severe injury to wheat and canola.

[0588] In summary, all combinations of 2,4DC plus metazachlor plus naproxil completely controlled Amaranthus retroflexus, Corn Poppy, Multiflora Ryegrass, Bluegrass, Wild Oats, Pigweed, Small-seed Beetle, Chickweed, and Silkweed at 28 DAT. Eight combinations had greater than or equal to 85% control of Nigella cumin. All combinations caused severe injury to wheat. 2,4DC alone controlled Amaranthus retroflexus, Corn Poppy, Nigella cumin, Pigweed at 400g, Multiflora Ryegrass at 200g, and Chickweed at all rates. Metazachlor plus naproxil had similar control / crop injury compared to the three-component combination. The table below highlights the unexpected synergy of the tested combinations.

[0589] Effects of 2,4-DC+metachlor+napropamide on wild oats at 28DAT

[0590]

[0591] α – measure of synergy, Y = yes; N = no

[0592] β and ρ - ratio - g ai / ha

[0593] Effects of 2,4-DC+metachlor+naprosulfuron on Nigella sativa L. at 28 DAT

[0594]

[0595] α – measure of synergy, Y = yes; N = no

[0596] β and ρ - ratio - g ai / ha

[0597] Example 29: Pre-emergence (PRE) weed efficacy / crop selectivity of a tank-mix of 2,4DC and dimethochlor.

[0598] In this example, a greenhouse study was conducted to determine the weed efficacy / crop selectivity of 2,4DC versus dimethochlor. The weeds tested in the study included multiflora ryegrass (Lolium perenne.multiflorum, LOLMU), wild mustard (Sinapis arvensis, SINAR), bluegrass (Poa annuaPOAAN), wild oats (Avena fatua, AVEFA), nigella (Alopecurus myosuroides, ALOMY), pigweed (Chenopodium albumCHEAL), small-seeded phalaris (PHAMI), chickweed (Stellariamedia, STEME), poppy (Papaver rhoeas, PAPRH), amaranthus retroflexus (Amaranthus retroflexus, AMARE), apera spica-venti (APSEB), and wild buckwheat (Polygonum convolvulus, POLCO). The crops tested were wheat and rapeseed.

[0599] Materials and methods

[0600] To determine PRE weed efficacy and crop selectivity, 2,4DC (36% SC) was applied alone at 50, 100, or 200 g ai / ha, and in combination with dimethochlor (Teridox 48%) at 333, 667, or 1000 g ai / ha. Other treatments included a single application of 2,4DC at 400 g ai / ha, dimethochlor alone at the aforementioned rates, and a tank mix of clomazone (Command 3ME 31.4%) plus dimethochlor at 100+1000 g ai / ha. An untreated test was included as a reference standard. Treatments were applied prior to germination on multiflora ryegrass, wild oats, wild buckwheat, nigella, small-seeded phragmites, chickweed, pigweed, corn poppy, silkweed, amaranth, wild mustard, bluegrass, canola, and wheat. Plants were grown in fiber flats (6"X10") containing Pennington soil and the flats were watered well before application and lightly after application. Flats were watered daily and fertilized after application of treatments. Treatments were applied with compressed air in an orbital spray chamber at 30 GPA using a TeeJet 8001E spray head at 40 PSI. Visible percent weed control and visible percent crop injury data were recorded 14, 21 and 28 days after treatment using a rating of 0 (no control / no injury) to 100 (complete plant death). Data (not included) were analyzed using Minitab statistical software with 95% confidence intervals.

[0601] Results for 28DAT:

[0602] 2,4DC alone provided control of Amaranthus retroflexus and Lolium multiflorum at ≥200 g ai / ha, control of Corn Poppy and Wild Oats at 400 g, control of Nigella cumin at ≥100 g, and control of Chickweed at all rates. 2,4DC was selective for wheat up to 200 g, and for canola up to 100 g. Dimethoate alone provided control of Chenopodium album at 1000 g ai / ha, control of Wild Oats, Wild Buckwheat, Phalaenopsis serrata, and Poa annua at ≥667 g, and control of Amaranthus retroflexus, Silkweed, Corn Poppy, Lolium multiflorum, and Chickweed at all rates. Dimethoate caused 18% injury to canola at 100 g and was not selective for wheat at any rate.

[0603] All combinations of 2,4DC and dimethochlor nearly controlled corn poppy, bluegrass, multiflora ryegrass, pigweed, Amaranthus retroflexus, silkweed, wild buckwheat, phalaenopsis serrata, wild oats, Nigella cumin, and chickweed. However, all combinations caused severe injury (>60%) to wheat at 28 DAT, and severe injury (>60%) to canola at 28 DAT. No combination achieved control of wild mustard.

[0604] Clomazone and dimethochlor provided control of all weeds except wild mustard. The tank-mix combination caused severe injury to wheat and canola.

[0605] In summary, in most cases, the 2,4DC and dimethoate tank mix combination controlled all weeds at 28 DAT. Almost all combinations resulted in high injury to wheat and oilseed rape. 200 g of 2,4DC alone was selective for wheat and had control of Amaranthus retroflexus, Lolium multiflorum, Chickweed, and Nigella cumin. The table below highlights the unexpected synergy of the tested combinations.

[0606] Effects of 2,4-DC+dimethochlor on Chenopodium album at 28DAT

[0607]

[0608] α – measure of synergy, Y = yes; N = no

[0609] β and ρ - ratio - g ai / ha

[0610] Effects of 2,4-DC+dimethochlor on wild oats at 28 DAT

[0611]

[0612] α – measure of synergy, Y = yes; N = no

[0613] β and ρ - ratio - g ai / ha

[0614] Effects of 2,4-DC+dimethochlor on Fagopyrum serrata at 28 DAT

[0615]

[0616] α – measure of synergy, Y = yes; N = no

[0617] β and ρ - ratio - g ai / ha

[0618] Effects of 2,4-DC+dimethochlor on Phalaenopsis microcarpa at 28 DAT

[0619]

[0620] α – measure of synergy, Y = yes; N = no

[0621] β and ρ - ratio - g ai / ha

[0622] Effects of 2,4-DC+dimethochlor on Nigella sativa L. at 28 DAT

[0623]

[0624] α – measure of synergy, Y = yes; N = no

[0625] β and ρ - ratio - g ai / ha

[0626] Effects of 2,4-DC+dimethochlor on Poa annua at 28 DAT

[0627]

[0628] α – measure of synergy, Y = yes; N = no

[0629] β and ρ - ratio - g ai / ha

[0630] Example 30: Weed control with a tank-mix combination of 2,4-DC and dimethochlor plus metazachlor.

[0631] In this example, a greenhouse study was conducted to determine the weed efficacy of 2,4DC (alone or in a three-component combination with dimethochlor and metazachlor) as a pre-emergence (PRE) treatment on the following weeds: multiflora ryegrass (Lolium perenne.multiflorum, LOLMU), wild mustard (Sinapis arvensis, SINAR), bluegrass (Poa annuaPOAAN), wild oats (Avena fatua, AVEFA), blackgrass (Alopecurus myosuroides, ALOMY), goosefoot (Chenopodium albumCHEAL), Phalaris minor (PHAMI), chickweed (Stellaria media, STEME), poppy (Papaver rhoeas, PAPRH), Amaranthus retroflexus (Amaranthus retroflexus, AMARE), Apera spica-venti, APSEB.

[0632] method:

[0633] 2,4-DC (SC 36%) was applied at 50, 100, or 200 g ai / ha alone or as a tank mix with dimethoate (48%) and metazachlor (43.1%). Dimethoate rates applied alone or in tank mixes were 500 or 1000 g ai / ha and metazachlor rates were 375 or 750 g ai / ha. Untreated tests were included as reference standards. Treatments were applied prior to germination of Lolium multiflorum, Wild Oats, Nigella Sativa, Phragmites australis, Chickweed, Chenopodium album, Corn Poppy, Silkweed, Amaranthus retroflexus, Wild Mustard, Poa annua, Canola, and Wheat. Plants were grown in fiber flats (6"X10") containing Pennington soil and the flats were well watered prior to application and lightly watered after application. Flats were watered and fertilized daily after application of the treatments. Treatments were applied with compressed air in an orbital spray chamber at 30 GPA using a TeeJet 8001E nozzle at 40 PSI. Visible percent weed control and visible percent crop injury data were recorded 14, 21, and 28 days after treatment using a rating scale of 0 (no control / no injury) to 100 (total plant death). Data (not included) were analyzed using Minitab statistical software with 95% confidence intervals.

[0634] result:

[0635] 2,4DC alone provided control of Amaranthus retroflexus, Corn Poppy, and Perennial Ryegrass at ≥200g ai / ha, control of wild oats at 400g, control of Nigella cumin at ≥100g, and control of Chickweed at all rates. 2,4-DC caused 11% injury to wheat at 200g and 11% injury to oilseed rape at 100g. (Dimethochlor + Metazachlor) alone provided control of all weeds except Brassica juncea. None of the combinations were safe for wheat; none showed more than 15% injury to rape, except for one combination at the highest rate that caused 28% injury. All combinations of 2,4-DC + Dimethochlor + Metazachlor provided control of all weed species except wild mustard, which only 4 combinations controlled. All combinations caused severe injury (>80%) to wheat, while causing >20% injury to rape.

[0636] In summary, all three-component tank mix combinations of 2,4-DC + dimethochlor + metazachlor controlled all weed species except mustard at 28 DAT. Almost all combinations resulted in high injury to wheat and rapeseed. 2,4DC alone was selective for wheat and rapeseed at 100g and 200g, respectively. 2,4DC controlled Nigella cumin, Lolium multiflorum, Amaranthus retroflexus, Corn Poppy, and Chickweed at 200g. The table below highlights the unexpected synergy of the tested combinations.

[0637] Effects of 2,4-DC+dimethochlor+metachlor on wild mustard at 28 DAT

[0638]

[0639] α – measure of synergy, Y = yes; N = no

[0640] β and ρ - ratio - g ai / ha

[0641] Example 31: Weed control with a tank-mix combination of 2,4-DC and mesotrione.

[0642] In this example, a greenhouse study was conducted to determine the weed efficacy of 2,4-DC, alone or in combination with mesotrione, as a pre-emergence (PRE) treatment of the following weeds: Datura (Datura stramonium, DATST), hemp (Abutilon theophrasti, ABUTH), hairy clover (Asteraceae bidens, BIDPA), Pennsylvania cocklebur (Xanthium strumarium, XANST), barnyard grass (Echinochloa crus-galli, ECHCG).

[0643] method:

[0644] 2,4-DC (SC 36%) was applied at 50, 100, or 200 g ai / ha alone or as a combination with mesotrione ( 40%) tank mix was applied at 25, 50 or 100 g ai / ha. Untreated tests were included as reference standards. Other treatments included mesotrione plus S-methoxazole (Dual II 82.4%) was applied as a tank mix of 100+525 g, and 2,4-DC was applied alone at 400 g. Treatments were applied before germination of Datura, Hemp, Hairy Clover, Pennsylvania Xanthium, Echinochloa, Sweet Corn, Yellow Corn, and Sorghum. Plants were grown in fiber flats (6"X10") containing Pennington soil, and the flats were well watered before application and lightly watered after application. Flats were watered and fertilized daily after application of treatments. Treatments were applied at 30 GPA with compressed air in an orbital atomization chamber, using a TeeJet 8001E nozzle at 40 PSI. Visible percent weed control and visible percent crop injury data were recorded 14, 21, and 28 days after treatment, using a rating of 0 (no control / no injury) to 100 (complete plant death). The (not included) data were analyzed using Minitab statistical software with 95% confidence intervals.

[0645] result:

[0646] 2,4-DC alone was safe on sweet and yellow corn at all three rates; was safe on sorghum at 25 and 50 g, and controlled hemp and datura at 50 or 100 g, and controlled cocklebur and hairy clover at 100 g.

[0647] Of the nine combinations of 2,4-DC plus mesotrione, two combinations were safe (≤10%) for sweet corn, five combinations were safe for sorghum, and seven combinations were safe for yellow corn. All combinations controlled barnyard grass. When mesotrione was added to the combinations at 50 or 100 g, green hemp and datura were controlled, except for green hemp when mesotrione was added at 50 g to 50 g of 2,4-DC, which did not control green hemp. Control of cocklebur and hairy clover was observed only in three combinations.

[0648] In summary, the combination of 2,4DC and mesotrione is unsafe for sweet corn, and the combination of 100g of 2,4DC plus 100g of mesotrione and 200g of 2,4DC is unsafe for sorghum. The combination is safe for yellow corn. All combinations are effective for barnyard grass; almost all combinations control velvetleaf and datura; only 3 combinations control cocklebur and hairy clover. 2,4DC alone is unsafe for sweet corn and sorghum at all rates (except the lowest rate). 2,4DC alone does not control any weeds except barnyard grass. Mesotrione is safe for both corns, and safe for sorghum at 25 or 50g. Mesotrione alone controls velvetleaf and datura at medium or highest rates, while it only controls cocklebur and hairy clover at the highest rate. The table below highlights the unexpected synergy of the tested combinations.

[0649] Effects of 2,4-DC+Mesotrione on Hemp at 28DAT

[0650]

[0651] α – measure of synergy, Y = yes; N = no

[0652] β and ρ - ratio - g ai / ha

[0653] Effects of 2,4-DC+Mesotrione on Datura stramonium at 28DAT

[0654]

[0655] α – measure of synergy, Y = yes; N = no

[0656] β and ρ - ratio - g ai / ha

[0657] Effects of 2,4-DC+Mesotrione on Xanthium sibiricum at 28 DAT

[0658]

[0659] α – measure of synergy, Y = yes; N = no

[0660] β and ρ - ratio - g ai / ha

[0661] Effects of 2,4-DC+Mesotrione on Trifolium repens at 28 DAT

[0662]

[0663] α – measure of synergy, Y = yes; N = no

[0664] β and ρ - ratio - g ai / ha

[0665] Example 32: Weed control with a tank mix combination of 2,4-DC and Pirovir plus sulfentrazone.

[0666] In this example, a greenhouse study was conducted to determine the weed efficacy of 2,4DC (alone or in combination with pyroximate plus sulfentrazone) as a pre-emergence (PRE) treatment on the following weeds: multiflora ryegrass (Lolium perenne.multiflorum, LOLMU), field bindweed (Convolvulus arvensis, CONAR), green foxtail (Setaria viridis, SETVI), wheatgrass (Elymus repens, AGGRE), chickweed (Stellaria media, STEME), wild oats (Avena fatua, AVEFA), small-seeded phragmites (Phalaris minor, PHAMI), white clover (Trifolium repens, TRFRE), dandelion (Taraxacum officinale, TAROF), yellow sedge (Cyperus esculentus, CYPES) ​​and Amaranthus retroflexus (Amaranthus retroflexus, AMARE).

[0667] method:

[0668] 2,4-DC (SC 36%) was applied at 0, 50, 100, or 200 g ai / ha alone or as a tank mix with Pirovir (WG 85%), 30, 60, or 90 g ai / ha, and Sulfonamide, 105 or 210 g ai / ha. Untreated tests were included as reference standards. Other treatments included a single application of 400 g of 2,4-DC, and a three-component tank mix of clomazone (Command 3ME 31.4%) 200 g and Pirovir 90 g plus Sulfonamide, 105 or 210 g. Treatments were applied while growing multiflora ryegrass, green foxtail, small-seeded phragmites, wild oats, thin wheatgrass, dandelions, chickweed, white clover, yellow sedge, Amaranthus retroflexus, field bindweed, canola, and wheat. Plants were grown in fiber flats containing Pennington soil and the flats were watered well before application and lightly after application. Flats were watered daily and fertilized after application of treatments. Treatments were applied with compressed air in an orbital spray chamber at 30 GPA using a TeeJet 8001E spray head at 40 PSI. Visible percent weed control and visible percent crop injury were recorded 14, 21 and 28 days after treatment using a rating of 0 (no control / no injury) to 100 (complete plant death). Data (not included) were analyzed using Minitab statistical software with 95% confidence intervals.

[0669] result:

[0670] All 18 three-component combinations had control (≥85%) of multiflora ryegrass, chickweed, field bindweed, green foxtail, white clover, wild oats, small-seeded phragmites, Amaranthus retroflexus, and dandelions at 28 DAT. 13 combinations achieved control of thinleaf wheat, while 10 combinations controlled yellow sedge. All combinations were unsafe (>10% injury) to wheat at 21 DAT, and unsafe (>10% injury) to canola at 28 DAT.

[0671] 2,4DC alone controlled Lolium multiflorum and wild oats at 400 g; chickweed at all rates; green foxtail at ≥100 g; and small-seeded phalaenopsis and Amaranthus retroflexus at 200 g. No rate achieved 85% control of Elytrimus, field bindweed, white clover, and yellow sedge. 2,4DC was safe on wheat at ≤100 g.

[0672] All two-component tank mix combinations of Pirovir plus sulfentrazone had control of multiflora ryegrass, chickweed, field bindweed, green foxtail, white clover, small-seeded phragmites, amaranth, and dandelions. Three combinations controlled thin wheatgrass. Control of wild oats was noted when Pirovir was added at 60 g or 90 g (at any rate of sulfentrazone). Control of yellow sedge was observed at 210 g of sulfentrazone (regardless of Pirovir rate). All combinations were unsafe to wheat at 21 DAT, and unsafe to rapeseed at 28 DAT.

[0673] In summary, all combinations of 2,4DC plus pyrochlore plus sulfentrazone and all combinations of pyrochlore plus sulfentrazone controlled multifloral ryegrass, chickweed, field bindweed, green foxtail, white clover, small-seeded phragmites, Amaranthus retroflexus, and dandelions. 2,4DC was safe in wheat at up to 100 g ai / ha and controlled multifloral ryegrass (400 g), chickweed (all rates), green foxtail (≥100 g), wild oats (400 g), small-seeded phragmites (≥200 g), Amaranthus retroflexus (≥200 g), and dandelions (all rates). The table below highlights the unexpected synergy of the tested combinations.

[0674] Effects of 2,4-DC+Pirovil+Sulfonamide on -28DAT of Elytrium sphaerocephalum

[0675]

[0676] α – measure of synergy, Y = yes; N = no

[0677] β and ρ - ratio - g ai / ha

[0678] Effects of 2,4-DC+Pirov+Sulfonamide on -28DAT of Wild Oats

[0679]

[0680] α – measure of synergy, Y = yes; N = no

[0681] β and ρ - ratio - g ai / ha

[0682] Effects of 2,4-DC+Pirovil+Sulfonamide on -28DAT of Cyperus rotundus

[0683]

[0684] α – measure of synergy, Y = yes; N = no

[0685] β and ρ - ratio - g ai / ha

[0686] Example 33: Weed control with a tank-mix combination of 2,4-DC and fluthiacet-methyl plus pyraclostrobin.

[0687] In this example, a greenhouse study was conducted to determine the weed efficacy of 2,4-DC, either alone or in combination with fluthiacet-methyl plus pyraclostrobin, against pre-emergence treatments of the following weeds: Palmer amaranth (Amaranthus palmeri, Amapa); Pennsylvania polygonum (Polygonum pensylvanicum, POLPY); Hemp (Abutilontheophrasti, ABUTH); Green foxtail (Setaria viridis, SETVI); Morning glory (Ipomoea spp.); Multiflora ryegrass (Lolium perenne L.ssp. multiflorum, LOLMU); Spiny yellow sedge (Sida spinosa, SIDSP); Yellow sedge (Cyperus esculentus, CYPES).

[0688] method:

[0689] 2,4-DC (46.2%) was applied alone at 31, 63, 125, 350 or 375 g ai / ha or as a combination with methicillin-methyl ( Tank mixes of 10.3%), 4.9 g ai / ha, and 85 WG, 85%), 30, 60, or 90 g ai / ha, applied alone or in combination with 2,4-DC at the above rates. (Methiothioate 0.69% plus Pirothioate 22.61%) was used as a standard, with a standard rate of 4.9 g ai / ha for methicillin and 165 g ai / ha for Pirothioate. An untreated test was included as a reference standard. The following weeds were screened: Palmer Amaranth, Pennsylvania Polygonum, Hemp, Green Setaria, Morning Glory, Multiflora Ryegrass, Prickly Yellow Flower, and Yellow Sedge. The screened crops were cotton, lentil, mung bean, dwarf bean, and cowpea. All plants were planted directly in 6"x10" fiber flats using Pennington soil. The flats were watered after sowing but before treatment. After application, the flats were placed in a greenhouse and lightly watered. Afterwards, the flats were watered and fertilized daily. Treatments were made with compressed air in an orbital spray chamber at 30 GPA using a TeeJet 8001E nozzle at 40 PSI. Visible percent weed control and crop injury were recorded 14, 21 and 28 days after treatment (DAT) using a rating scale of 0 (no control / no injury) to 100 (total plant death). Data (not included) were analyzed using Minitab statistical software with 95% confidence intervals.

[0690] result:

[0691] All 18 three-component combinations had control (≥85%) of multiflora ryegrass, chickweed, field bindweed, green foxtail, white clover, wild oats, small-seeded phragmites, Amaranthus retroflexus, and dandelions at 28 DAT. 13 combinations achieved control of thinleaf wheat, while 10 combinations controlled yellow sedge. All combinations were unsafe (>10% injury) to wheat at 21 DAT, and unsafe (>10% injury) to canola at 28 DAT.

[0692] Combinations of 2,4-DC plus methicillin-methyl and pyrochlore applied as PRE, all tank-mix combinations controlled sedge, Palmer amaranth, green foxtail, and multiflora ryegrass. 14 of 15 combinations controlled Pennsylvanian Polygonum, 11 combinations controlled hemp, 1 combination controlled morning glory, and no combination controlled yellow sedge. When applied alone, 2,4-DC controlled sedge at 31 g ai / ha and green foxtail at 125 g. Pennsylvanian Polygonum and multiflora ryegrass were controlled at 250 g of 2,4-DC; Palmer amaranth and hemp were controlled at 375 g of 2,4-DC. Fluthiacet-methyl 4.9 g plus Pirovi 30 g controlled spiny yellow flower, Palmer amaranth, green foxtail, and multiflora ryegrass, Fluthiacet-methyl 4.9 g plus Pirovi 60 g controlled Pennsylvania Polygonum and Hemp, Fluthiacet-methyl 4.9 g plus Pirovi 90 g controlled morning glory. In the evaluation, All weeds are controlled.

[0693] 2,4DC plus flumethoxam-methyl plus pyrothricin was generally safe for cotton when applied at pyrothricin rates less than 90 g. Five of 15 combinations of 2,4DC plus flumethoxam-methyl plus pyrothricin were safe for mung bean, four combinations were safe for cowpea, three combinations were safe for dwarf bean, and all combinations injured lentil. 2,4DC applied alone PRE was safe for cotton, mung bean, dwarf bean, and cowpea at all rates and was not safe for lentil at any rate. Flumethoxam-methyl 4.9 g plus pyrothricin 30 g was safe for mung bean and cowpea, and flumethoxam-methyl 4.9 g plus pyrothricin up to 60 g was safe for cotton. All treatments of flumethoxam-methyl and pyrothricin caused injury to dwarf bean and lentil. Anthem was not safe for any crop in the evaluation.

[0694] In summary, 2,4DC alone controlled A. spinulosa at 31 g ai / ha, A. viridis at 125 g, A. pennsylvanicum and Lolium multiflorum at 250 g, and A. palmer's amaranth and A. ramidus at 375 g. All combinations of 2,4DC plus methicillin-methyl 4.9 g and Pyrovel 30, 60, or 90 g controlled A. spinulosa, A. palmer's amaranth, A. viridis, and Lolium multiflorum (Anthem, included as a standard, rated at 9 fl oz / A, controlled all agents in the evaluation).

[0695] 2,4DC applied alone was safe to cotton, mung bean, cowpea and dwarf bean at all rates and unsafe to lentil at any rate. Fluthiacet-methyl plus Pirovir damaged mung bean and cowpea (60 g Pirovir), damaged cotton (90 g Pirovir) and damaged lentil and dwarf bean at all rates. Anthem at the standard rate damaged all crops.

[0696] The table below highlights the unexpected synergies of the test combinations.

[0697] Effects of 2,4-DC+methylthiazide+pirowei on -28DAT of Polygonum pennsylvanicum

[0698]

[0699] α – measure of synergy, Y = yes; N = no

[0700] β and ρ - ratio - g ai / ha

[0701] Effects of 2,4-DC+methylthiazate+pirowei on -28DAT of Hemp

[0702]

[0703] α – measure of synergy, Y = yes; N = no

[0704] β and ρ - ratio - g ai / ha

[0705] Example 34: Weed control with a tank mix combination of 2,4-DC and napropamide.

[0706] In this example, a greenhouse study was conducted to determine the weed efficacy of 2,4DC (alone or in combination with naproxen) as a pre-emergence (PRE) treatment on the following weeds: Phalaris minor (PHAMI); Chenopodium album (CHEAL); Alopecurus myosuroides (ALOMY); Polygonum convolvulus (POLCO); Avena fatua (AVEFA); Poa annua (POANN); Stellaria media (STEME); Lolium perenne L.ssp. multiflorum (LOLMU); and Sinapis arvensis (SINAR).

[0707] method:

[0708] 2,4-DC (SC 36%) was applied alone or as a combination with naproxenamide ( -50DF) tank mix was applied at 315, 630 or 1260 g ai / ha. Untreated tests were included as a reference standard. Clomazone (Command 31.4%) plus naproxenamide as standard. Small-seeded phalaenopsis, quinoa, nigella, wild buckwheat, wild oats, bluegrass, chickweed, multiflora ryegrass, wild mustard, and canola were sown directly into 6x10" fiber flats filled with Pennington soil. Flats were watered after sowing but before treatment. After application, flats were placed in a greenhouse and lightly watered. Thereafter, flats were watered and fertilized daily. Treatments were applied with compressed air in an orbital spray chamber at 30 GPA using a TeeJet 8001E spray head at 40 PSI. Visible percent weed control / crop injury was recorded 14, 21, and 27 days after treatment (DAT) using a rating of 0 (no control / no injury) to 100 (total plant death). Data (not included) were analyzed using Minitab statistical software with 95% confidence intervals.

[0709] result:

[0710] 2,4DC plus napropamide provided control of chickweed in all tank mix combinations. Eleven of the 15 tank mixes controlled bluegrass, 12 controlled phalaenopsis and pigweed, 10 controlled multiflora ryegrass, 9 controlled nigella, and 1 combination controlled wild buckwheat and wild oats. Three tank mixes of 2,4-DC plus napropamide were safe for canola. 2,4-DC applied alone controlled chickweed at 31.2 g ai / ha, controlled pigweed and injured canola at 125 g, and controlled nigella and multiflora ryegrass at 250 g. 2,4-DC applied alone failed to control phalaenopsis, wild buckwheat, wild oats, bluegrass, and wild mustard. Napropamide alone controlled bluegrass at 630 g, pigweed, bluegrass, and multiflora ryegrass at 1260 g, and was safe for canola at all rates. 375 g of clomazone plus 1260 g of naproxen controlled all weeds except wild mustard and injured the rapeseed.

[0711] In summary, 2,4DC napropamide controlled chickweed at all rates, pigweed, kenaf, and bluegrass at most rates, and all tank-mix combinations for ≥125 g of 2,4DC controlled nigella and perennial ryegrass. 2DC alone controlled chickweed at all rates, pigweed at 125 g, and nigella and perennial ryegrass at 250 g. Napropamide alone controlled nigella at 630 g and pigweed, bluegrass, and perennial ryegrass at 1260 g. The three tank-mix combinations did not injure canola when 2,4DC was applied alone at ≤62.5 g, or were not injured by napropamide alone at all three rates. The inclusion of clomazone plus napropamide as a standard for comparison controlled all weeds except wild mustard and was unsafe for canola. The table below highlights the unexpected synergy of the tested combinations.

[0712] Effects of 2,4-DC+napropamide on -28DAT of Phalaenopsis microcarpa

[0713]

[0714] α – measure of synergy, Y = yes; N = no

[0715] β and ρ - ratio - g ai / ha

[0716] Effects of 2,4-DC+napropamide on -28DAT of Chenopodium album

[0717]

[0718] α – measure of synergy, Y = yes; N = no

[0719] β and ρ - ratio - g ai / ha

[0720] Effects of 2,4-DC+napropamide on -28DAT of Nigella sativa

[0721]

[0722] α – measure of synergy, Y = yes; N = no

[0723] β and ρ - ratio - g ai / ha

[0724] Effects of 2,4-DC+napropamide on -28DAT of wild buckwheat

[0725]

[0726] α – measure of synergy, Y = yes; N = no

[0727] β and ρ - ratio - g ai / ha

[0728] Effects of 2,4-DC+napropamide on bluegrass at -28DAT

[0729]

[0730] α – measure of synergy, Y = yes; N = no

[0731] β and ρ - ratio - g ai / ha

[0732] Example 35: Weed control with a tank-mix combination of 2,4-DC and dimethochlor plus napropamide.

[0733] In this example, a greenhouse study was conducted to determine the weed efficacy of 2,4DC (alone or in combination with dimethoate and naproxen) as a pre-emergence (PRE) treatment on the following weeds: Chenopodium album (CHEAL); Amaranthus retroflexus (AMARE); Apera spica-venti (APESV); Lolium perenne L.ssp.multiflorum (LOLMU); Papaver rhoeas (PARPH); Phalaris minor (PHAMI); Poa annua (POAAN); Shepherd's purse (Capsella bursa-pastoris, CAPBP); black grass (Alopecurusmyosuroides, ALOMY); wild buckwheat (Polygonum convolvulus, POLCO); wild oats (Avena fatua, AVEFA); wild mustard (Sinapis arvensis, SINAR); chickweed (Stellariamedia, STEME). The crops screened were wheat and rapeseed.

[0734] method:

[0735] 2,4-DC (SC 36%) was applied at 50, 100, or 200 g ai / ha alone or as a tank mix with dimethoate (48%) and napropamide (DF 50). Dimethoate rates applied alone or in tank mixes were 500 or 1000 g ai / ha, and napropamide rates were 630 or 1,260 g ai / ha. Untreated tests were included as reference standards. Clomazone ( 3ME, 31.4%), 100 g ai / ha plus dimethoate, 1000 g, plus naproxil, 1260 g, as a standard for comparison. Treatments were applied before Chenopodium album, Amaranthus retroflexus, Silkweed, Lolium multiflorum, Corn Poppy, Phragmites australis, Poa annua, Shepherd's purse, Nigella sativa, Wild buckwheat, Wild oats, Wild mustard, Chickweed, Wheat, and Canola PRE. All plants were planted directly in 6x10" fiber flats with Pennington soil. Flats were watered after sowing but before treatment. After application, flats were placed in a greenhouse and lightly watered. Flats were then watered and fertilized daily. Spray volumes were applied with compressed air at 40 PSI in an orbital mist chamber using a TeeJet 8001E nozzle at 30 GPA. Visible percent weed control and crop injury data were recorded at 14, 21, and 28 days after treatment (DAT).

[0736] result:

[0737] 2,4-DC alone at 50 g ai / ha controlled chickweed (≥85% injury), and 100 g controlled nigella and wild buckwheat. At 200 g, it controlled pigweed, Amaranthus retroflexus, Lolium multiflorum, and corn poppy, and at 400 g, it controlled small-seeded phragmites, bluegrass, and shepherd's purse. 2,4-DC alone was safe to wheat and canola (≤10% injury) when applied at 50 and 100 g. 2,4-DC plus dimethoate and naproxen controlled all weeds at all rates except wild mustard. Four of the 12 combinations controlled wild mustard. One combination of 2,4-DC plus dimethoate and naproxen was safe to canola, and all combinations injured wheat. Clomazone plus dimethoate and naproxen controlled all weeds and caused injury to both crops.

[0738] In summary, 2,4DC controlled pigweed, Amaranthus retroflexus, Lolium multiflorum, Corn Poppy, Nigella cumin, Wild Oats, and Chickweed when applied alone at ≤200 g ai / ha. All combinations of 2,4-DC plus dimethoate and naproxenide controlled all weeds except wild mustard.

[0739] The table below highlights the unexpected synergies of the test combinations.

[0740] PRE effect of 2,4-DC+dimethochlor+napropamide on Brassica juncea (28DAT)

[0741]

[0742] α – measure of synergy, Y = yes; N = no

[0743] β and ρ - ratio - g ai / ha

[0744] Example 36: Weed control with a tank-mix combination of 2,4-DC and mesosulfuron-methyl.

[0745] In this example, a greenhouse study was conducted to determine the weed efficacy of 2,4DC (alone or in combination with methylsulfuron-methyl (AlluXP 60%)) as a post-emergence treatment on the following weeds: multifloral ryegrass (Lolium perenne L.ssp. multiflorum, LOLMU); wild oats (Avena fatua, AVEFA); goosefoot (Chenopodium album, CHEAL); blackgrass (Alopecurus myosuroides, ALOMY); small-seeded phragmites (Phalaris minor, PHAMI); bluegrass (Poa annua, POAAN); poppy (Papaverrhoeas, PARPH); chickweed (Stellaria media, STEME); Amaranthus retroflexus (Amaranthus retroflexu, AMARE); wild mustard (Sinapis arvensis, SINAR); wild buckwheat (Polygonum convolvulus, POLCO). The crops screened were wheat and barley.

[0746] method:

[0747] 2,4-DC (SC 36%) was applied at 50, 100, or 200 g ai / ha alone or as a tank mix with methylsulfuron-methyl (60%) at 6, 9, or 12 g ai / ha. Untreated tests were included as reference standards. TM , 26.3%), 271g ai / ha, and application of thifensulfuron-methyl ( SG, 75%), 17.4 g ai / ha, was used as a standard for comparison. POST treatments were applied to the following materials, with the height given in parentheses: multiflora ryegrass (2-4"), wild oats (3-4"), pigweed (1"), black cumin (2-3"), small-seeded phragmites (1-2"), bluegrass (0.5"), poppy (1"), chickweed (0.5"), amaranth (1"), wild mustard (1"), wild buckwheat (1"), wheat (3-4") and barley (2-4"). All plants were planted directly in 3" plastic pots with Pennington soil. After application, the plants were placed in a greenhouse and the leaves were allowed to dry for 24 hours. Afterwards, the plants were watered and fertilized daily. The spray volume was 30 GPA using compressed air at 40 PSI in an orbital spray chamber using a TeeJet 8001E nozzle. Visible percent weed control and crop injury were recorded 7, 14, 21 and 28 days after treatment (DAT) using a rating scale of 0 (no control / no injury) to 100 (total plant death). Data (not included) were analyzed using Minitab statistical software with 95% confidence intervals.

[0748] result:

[0749] 2,4-DC applied alone was safe to barley at 50 g ai / ha and safe to wheat at ≤100 g. All combinations of 2,4-DC plus metsulfuron-methyl controlled pigweed, phalaenopsis foetida, corn poppy, chickweed, amaranth, and wild mustard (≥85% injury), and 2 combinations controlled multiflora ryegrass. Wild oats, nigella, and bluegrass were not controlled by any of the tank-mix combinations. Three combinations did not injure wheat, and one tank-mix combination was safe to barley. HUSKIE TM Controls pigweed, corn poppy, amaranth, wild mustard, and wild buckwheat and is safe for barley; Controls pigweed, chickweed, amaranth and wild buckwheat and is safe for wheat and barley.

[0750] In summary, 2,4DC failed to control any weeds at all rates when applied alone in POST and was safe for barley at 50 g ai / ha and for wheat at ≤ 100 g. All tank mix combinations of 2-DC plus metsulfuron-methyl controlled pigweed, phalaenopsis foetida, corn poppy, chickweed, amaranth and wild mustard, with 3 combinations being safe for wheat and 1 combination being safe for barley. The table below highlights the unexpected synergy of the tested combinations.

[0751] Effects of 2,4-DC+methylsulfuron-methyl on Lolium multiflorum at 28 DAT

[0752]

[0753] α – measure of synergy, Y = yes; N = no

[0754] β and ρ - ratio - g ai / ha

[0755] Example 37: Weed control with a tank mix combination of 2,4-DC and atrazine.

[0756] In this example, a greenhouse study was conducted to determine the weed efficacy of 2,4-DC, alone or in combination with atrazine, as a pre-emergence (PRE) treatment of the following weeds: Pennsylvania cocklebur (Xanthium strumarium, XANST); hemp (Abutilon theophrasti, ABUTH); Datura (Datura stramonium, DATST); barnyard grass (Echinochloa crus-galli, ECHCG); and amaranthus retroflexus (Amaranthus retroflexus, AMARE).

[0757] method:

[0758] 2,4-DC (SC 36%) was applied alone at 50, 100, or 200 g ai / ha or as a tank mix with atrazine (4L, 42.6%) at 140, 280, or 560 g ai / ha. Untreated tests were included as reference standards. S-Methochlor (DUAL II 82.4%), 525 g ai / h plus atrazine, 560 g ai / h, as a standard for comparison. Xanthium sibiricum, Hemp, Datura, Echinochloa revoluta, Amaranthus retroflexus, Corn, Sweet Corn, and Sorghum were sown directly into 6"x10" fiber flats using Pennington soil. Flats were watered after sowing but before treatment. After application, the flats were placed in the greenhouse and lightly watered. Thereafter, the flats were watered and fertilized daily. Treatments were applied with compressed air in an orbital spray chamber at 30 GPA using a TeeJet 8001E nozzle at 40 PSI. Visible percent weed control and crop injury were recorded 14, 21, and 28 days after treatment (DAT) using a rating of 0 (no control / no injury) to 100 (complete plant death). Data were analyzed using Minitab statistical software with 95% confidence intervals.

[0759] result:

[0760] 2,4-DC applied alone at ≥50 g ai / ha controlled barnyard grass 28 DAT. 2,4-DC applied alone at ≥200 g controlled hemp and Amaranthus retroflexus, and 400 g of 2,4-DC applied alone controlled Datura stramonium. 2,4-DC applied alone did not control Xanthium strumarium at any rate. All combinations of 2,4-DC plus atrazine controlled hemp, Datura stramonium, barnyard grass, and Amaranthus retroflexus. Six tank-mix combinations of 2,4-DC plus atrazine controlled Xanthium strumarium. 2,4DC applied alone at ≤200 g was safe for corn, and ≤100 g of 2,4DC did not injure sweet corn or sorghum (>10%). 2,4-DC plus atrazine as a tank mix was generally well tolerated for corn, sweet corn, and sorghum.

[0761] In summary, 2,4DC alone controlled barnyard grass at all rates, controlled hemp and Amaranthus retroflexus at 200 g ai / ha, and controlled Datura stramonium at 400 g. Six of the nine combinations of 2,4DC plus atrazine controlled Xanthium strumarium, and all combinations controlled hemp, Datura stramonium, barnyard grass, and Amaranthus retroflexus. The table below highlights the unexpected synergistic effects of the tested combinations.

[0762] Effects of 2,4-DC+atrazine on Xanthium sibiricum at -28 DAT

[0763]

[0764] α – measure of synergy, Y = yes; N = no

[0765] β and ρ - ratio - g ai / ha

[0766] Effects of 2,4-DC+atrazine on 28DAT of Hemp

[0767]

[0768] α – measure of synergy, Y = yes; N = no

[0769] β and ρ - ratio - g ai / ha

[0770] Example 38: Weed control with a tank-mix combination of 2,4-DC and Pirowei.

[0771] In this example, a greenhouse study was conducted to determine the weed efficacy of 2,4-DC, alone or in combination with Pirovir, as a pre-emergence (PRE) treatment of the following weeds: Cyperus esculentus (CYPES); Lolium perenne spp. multiflorum (LOLMU); Morning glory (Ipomeaspp); Amaranthus retroflexus (AMARE); Hemp (Abutilontheophrasti, ABUTH); Kochia scoparia (KCHSC); and Field bindweed (Convolvulus sarvensis, CONAR).

[0772] method:

[0773] 2,4-DC (SC 36%) was applied at 0, 50, 100, or 200 g ai / ha alone or as a tank mix with Pirovir (85%) at 30, 60, or 90 g ai / ha. Untreated tests were included as reference standards. TM , 23.3%) was applied at 165g ai / ha as a standard control. Yellow sedge, multiflora ryegrass, morning glory, Amaranthus retroflexus, hemp, Kochia scoparia, field bindweed, wheat and corn were sown directly into 6"x10" fiber flats using Pennington soil. Flats were watered after sowing but before treatment. After application, the flats were placed in the greenhouse and lightly watered. Thereafter, the flats were watered and fertilized daily. Treatments were applied with compressed air in an orbital spray chamber at 40psi and 30GPA spray volume using a TeeJet 8001E nozzle. Visible percent weed control and crop injury were recorded 14, 21 and 28 days after treatment (DAT) using a rating of 0 (no control / no injury) to 100 (complete plant death). Data were analyzed using Minitab statistical software with 95% confidence intervals.

[0774] result:

[0775] 2,4-DC applied alone at ≥50 g ai / ha controlled Kochia scoparia (≥85%), Nigella cuminata or Amaranthus retroflexus at ≥200 g, and Hemp at 400 g.

[0776] 2,4-DC was selective for wheat (≤10% injury) when applied at ≤100 g, and for corn when applied at ≤200 g. All combinations of 2,4-DC plus Pirovir controlled multiflora ryegrass, Amaranthus retroflexus, and Kochia scoparia. All combinations controlled Hemp, except when 2,4-DC was applied at 50 gai / ha and Pirovir was applied at 30 gai / ha. No combination of 2,4-DC plus Pirovir controlled Yellow sedge, Morning glory, or Field bindweed. Eight of the nine combinations injured wheat, while six of the nine combinations of 2,4-DC plus Pirovir injured corn. ANTHEM applied at 165 g ai / ha TM Controlled all weeds except morning glory and field bindweed.

[0777] In summary, 2,4DC alone controlled Kochia scoparia at all rates, controlled Lolium multiflorum and Amaranthus retroflexus at 200 g ai / ha, and controlled Hesperidium avium at 400 g. 2,4DC alone did not injure wheat at 50 or 100 g, while being safe for corn up to and including 200 g ai / ha. All combinations of 2.4DC plus the tank mix of Piroway controlled Lolium multiflorum, Amaranthus retroflexus, and Kochia scoparia, some combinations controlled Hesperidium avium, and none of the combinations controlled Sedge, Morning Glory, or Field Bindweed. One combination did not injure wheat. Safety results for corn were good for the combinations tested.

[0778] The table below highlights the unexpected synergies of the test combinations.

[0779] Effects of 2,4-DC+Pirovec on morning glory at -28DAT

[0780]

[0781] α – measure of synergy, Y = yes; N = no

[0782] β and ρ - ratio - g ai / ha

[0783] Example 39: Weed control with a tank-mix combination of 2,4-DC and pyraclostrobin plus mefenacet-butyl.

[0784] In this example, a greenhouse study was conducted to determine the weed efficacy of 2,4DC (alone or in combination with pyraclostrobin plus mefenacet) as a pre-emergence (PRE) treatment on the following weeds: Amaranthus retroflexus (AMARE); Phalaris minor (PHAMI); Thistle (Cirsium arvense (CIRAR); Dandelion (Taraxacum officinale (TAROF); Green foxtail (Setariaviridis (SETVI); Wild oats (Avena fatua (AVEFA); White clover (Trifolium repens (TRFRE); Yellow sedge (Cyperus esculentus (CYPES); Multiflora ryegrass (Lolium perenne) spp.multiflorum,LOLMU); Stellaria media (STEME); Elytrigia repens (AGRRE); Convolvulus arvensis (CONAR).

[0785] method:

[0786] 2,4-DC (SC 36%) was applied at 50, 100, or 200 g ai / ha alone or as a combination with pyraclostrobin (KIH485WG 85%) and ethylpyraclostrobin ( 22.3%) tank mix. Piroxicam was applied alone or in a tank mix at a rate of 30, 60 or 90 g ai / ha and mefenacet was applied at a rate of 25 g ai / ha. An untreated test was included as a reference standard. Clomazone ( 3ME), 200g, plus Pirowei, 90g, and Ethylpyrazone, 25g, as a standard control. Amaranthus retroflexus, small-seeded phragmites, field thistle, dandelion, green foxtail, wild oats, white clover, yellow sedge, multiflora ryegrass, chickweed, thin wheatgrass, field bindweed, rapeseed and wheat were sown directly into 6"x10" fiber flats using Pennington soil. The flats were watered after sowing but before treatment. After application, the flats were placed in a greenhouse and lightly watered. Afterwards, the flats were watered and fertilized daily. Treatments were conducted with compressed air in an orbital atomization chamber at 30GPA using a TeeJet 8001E nozzle at 40PSI. Visible percentage weed control and crop injury were recorded 14, 21 and 28 days after treatment (DAT), using a rating of 0 (no control / no injury) to 100 (complete plant death). The data (not included) were analyzed using Minitab statistical software with 95% confidence intervals.

[0787] result:

[0788] 2,4-DC alone at ≥50 g ai / ha controlled field thistle, dandelion, or chickweed (≥85%). At 100 g applied, 2,4-DC controlled Amaranthus retroflexus and Lolium multiflorum; and at 200 g controlled Phalaris foetida and wild oats. All tank-mix combinations of 2,4-DC with pyraclostrobin plus mefenacet controlled Amaranthus retroflexus, Phalaris foetida, field thistle, dandelion, Green foxtail, wild oats, White clover, Lolium multiflorum, and chickweed. Eight of the nine tank-mix combinations controlled Elymus ovata and Field Bindweed; one combination controlled Cyperus rotundus. Clomazone plus pyraclostrobin and mefenacet applied as a standard controlled all weeds except Cyperus rotundus.

[0789] 2,4DC applied alone controlled thistle, dandelion, green foxtail, and chickweed at all rates, and Amaranthus retroflexus, Lolium multiflorum, Phalaenopsis sphaerocephalus, and wild oats at some rates. 2,4DC was safe for wheat at low rates and safe for canola at most rates. All combinations of 2,4DC plus pyraclostrobin and ethylpyraclostrobin controlled all weeds except Elytium wilfordii and Field bindweed, which were controlled by most combinations, and 1 combination controlled yellow sedge. No combination was safe for canola. The table below highlights the unexpected synergy of the tested combinations.

[0790] Effects of 2,4-DC+pirowei+fenacet-butyl on -28DAT of Cyperus rotundus

[0791]

[0792] α – measure of synergy, Y = yes; N = no

[0793] β and ρ - ratio - g ai / ha

[0794] Unexpected crop safety was observed for at least 7 crops: barley, rapeseed, maize, cowpea, sorghum, sweet corn and wheat. This unexpected effect safety was documented in the following PRE / POST studies.

[0795] Example 40: Crop safety of a tank-mix combination of 2,4-DC and mesosulfuron-methyl.

[0796] In this example, a greenhouse study was conducted to determine the crop safety and weed efficacy of 2,4DC, alone or in combination with metsulfuron-methyl, for post-emergence (POST) treatment of wild oats (Avena fatua, AVEFA), wild buckwheat (Polygonum convolvulus, POLCO), chickweed (Stellaria media, STEME), quinoa (Chenopodium album, CHEAL), wild mustard (Sinapis arvensis, SINAR), and multiflora ryegrass (Lolium perenne L.ssp.multiflorum, LOLMU). Treatments were applied to barley and wheat crops.

[0797] method:

[0798] 2,4-DC (SC 36%) was applied alone at 125, 170, or 250 g ai / ha or as a tank mix with metsulfuron-methyl (AllyXP 60%) at 2, 3, or 4 g ai / ha. Untreated tests were included as reference standards. Thifensulfuron-methyl + tribenuron-methyl + metsulfuron-methyl (Accurate 37.5% + 18.75% + 15%), 31.48g ai / ha, or thifensulfuron-methyl + benzylsulfuron-methyl (HARMONY SG, 33.33% + 16.67%), 19.95g ai / ha, as commercial standard. Non-ionic surfactant (NIS) was added to all treatments, 0.5% v / v. All plants were planted directly into 3" plastic pots using metro-mix as the growing medium. At the time of treatment, Chenopodium album was 1.75", Chickweed was 2", Wild Mustard was 2.25", Wild Oats was 5.5", Wild Buckwheat was 2-5", Multiflora Ryegrass was 2-3", Wheat was 5.5", and Barley was 4.5" in height. Plants were watered well before application and not watered for 24 hours after application. Plants were watered and fertilized daily after application of treatment. Each treatment was replicated 4 times. The treated plates were placed in a random block design in the greenhouse. Treatments were applied with compressed air in an orbital spray chamber at 30GPA using a TeeJet 40PSI. 8001E sprinkler. Visible percent wheat and barley injury and weed control were recorded 7, 14, 21 and 28 days after treatment (DAT) using a rating of 0 (no control / no injury) to 100 (complete plant death). Data were analyzed using Minitab statistical software with 95% confidence intervals.

[0799] result:

[0800] All tank mix applications of 2,4-DC plus methylsulfuron had ≥85% control of chickweed, wild mustard, and pigweed, and 10 combinations controlled wild buckwheat. Wild oats and multiflora ryegrass were not controlled by any tank mix combination. No combination injured wheat, 2 combinations caused moderate injury to barley, and barley was safe to all other tank mix combinations.

[0801] Metsulfuron-methyl alone controlled wild buckwheat, chickweed, wild mustard, and pigweed at all rates and was safe for both crops at all rates. Thifensulfuron-methyl plus benzylsulfuron-methyl plus metsulfuron-methyl or thifensulfuron-methyl plus benzylsulfuron-methyl controlled wild buckwheat, wild mustard, chickweed, and pigweed and were safe for barley and wheat; no standard formulation combination controlled wild oats or multiflora ryegrass.

[0802] The 7-day safety results showed a favorable injury profile for the combination treatment compared to the single components applied alone. 2,4-DC applied alone was safe for both wheat and barley at all rates. Compared to when 2,4DC was applied with metsulfuron-methyl at the same rate, 2,4DC alone at 170 g ai / hec caused greater than 10% damage to the plants. Thus, in general, the combination showed a better safety profile compared to 2,4DC applied at 170 g ai / hec and metsulfuron-methyl at 3 g ai / hec.

[0803] Effects of 2,4-DC+methylsulfuron-methyl on -7DAT of barley

[0804]

[0805] ε-% measurement of crop damage: safe (0-10%); moderate (11-20%); damaged (≥20)

[0806] β and ρ - ratio - g ai / ha

[0807] Effects of 2,4-DC+methylsulfuron-methyl on -7DAT of wheat

[0808]

[0809] ε-% measurement of crop damage: safe (0-10%); moderate (11-20%); damaged (≥20)

[0810] β and ρ - ratio - g ai / ha

[0811] Example 41: Crop safety of a tank mix combination of 2,4-DC and thifensulfuron-methyl.

[0812] In this example, a greenhouse study was conducted to determine the crop safety and weed efficacy of 2,4DC, alone or in combination with thifensulfuron-methyl, for post-emergence (POST) treatment of the following weeds: wild oats (Avena fatua, AVEFA), wild buckwheat (Polygonum convolvulus, POLCO), chickweed (Stellaria media, STEME), quinoa (Chenopodium album, CHEAL), wild mustard (Sinapis arvensis, SINAR). Treatments were applied to wheat and barley crops.

[0813] method:

[0814] 2,4-DC (SC 36%) was applied at 0, 125, 170, 210, or 250 g ai / ha alone or as a tank mix with methylsulfuron-methyl (AllyXP 60%) at 50, 75, or 100 g ai / ha. Untreated tests were included as reference standards. Thifensulfuron-methyl + tribenuron-methyl + metsulfuron-methyl (Accurate 37.5% + 18.75% + 15%), 49g ai / ha, or thifensulfuron-methyl + benzylsulfuron-methyl (HARMONY SG, 33.33% + 16.67%), 21 g ai / ha, as a commercial standard. Nonionic surfactant was added to all treatments, 0.5% v / v. Treatments were applied to wheat (5.5"), barley (5"), wild oats (5.5"), chickweed (2"), wild buckwheat (3"), and quinoa (2"). All plants were sown directly into 3" plastic pots using metro-mix as the growing medium and the pots were well watered before application and watered 24 hours after application. Plants were watered and fertilized daily after treatment application. Each treatment was replicated 4 times. Treatments were applied with compressed air in an orbital spray chamber at 30 GPA using a TeeJet 8001E spray head at 40 PSI. Visible percent wheat and barley injury and weed control were recorded at 7, 14, 21 and 28 days after treatment (DAT) using a rating of 0 (no control / no injury) to 100 (total plant death). Data were analyzed using Minitab statistical software with 95% confidence intervals.

[0815] result:

[0816] All tank mix applications of 2,4-DC plus thifensulfuron-methyl had ≥85% control of wild buckwheat, chickweed, wild mustard, and pigweed. Wild oats were not controlled by any combination. All 6 combinations were safe for wheat when 2,4-DC was applied at 170 g ai / ha or lower (with thifensulfuron-methyl), and 2 combinations were safe for wheat when 210 g of 2,4-DC was applied. Seven tank mix combinations of 2,4-DC + thifensulfuron-methyl were safe for barley. 2,4-DC alone was safe for wheat at up to 170 g ai / ha, but 2,4-DC alone was not safe for barley at any rate. Thifensulfuron-methyl alone controlled all weeds except wild oats and was safe for both crops. The data suggest that thifensulfuron-methyl has a safening effect because it reduces the damage of 2,4-DC to wheat and barley. When 2,4-DC was applied together with thifensulfuron-methyl, both injuries were reduced in barley and wheat compared to the same rates of 2,4-DC alone.

[0817] Applications of 2,4-DC alone at greater than and equal to 125 g ai / ha or thifensulfuron-methyl alone at 50 g ai / ha caused injury to barley and wheat, but when applied together at the same rate, the injury of the co-application of the herbicides was reduced by ≥ 10% compared to 2,4-DC alone. Thus, the combination provides a better safety profile than 2,4DC alone.

[0818] Crop injury of barley at -14DAT by 2,4-DC+thifensulfuron-methyl

[0819]

[0820] Ω,φ - measure of % crop damage for each individual ai: safe (0-10%); moderate (11-20%); damaged (≥20)

[0821] ε – a measure of % crop damage for the combination tested ai

[0822] β and ρ - ratio - g ai / ha

[0823] Crop injury of wheat at -14DAT by 2,4-DC+thifensulfuron-methyl

[0824]

[0825] Ω,φ - measure of % crop damage for each individual ai: safe (0-10%); moderate (11-20%); damaged (≥20)

[0826] ε – a measure of % crop damage for the combination tested ai

[0827] β and ρ - ratio - g ai / ha

[0828] Example 42: Crop safety of a tank-mix combination of 2,4-DC and sulfentrazone.

[0829] In this example, greenhouse studies were conducted to determine the crop selectivity and weed efficacy of 2,4-DC, either alone or in combination with sulfentrazone, for pre-emergence (PRE) treatment of the following weeds: Palmer amaranth (Amaranthuspalmeri, AMAPA); ragweed (Ambrosia artemisiifolia, AMBEL); Pennsylvanian Polygonum (Polygonumpensylvanicum, POLPY); hemp (Abutilon theophrasti, ABUTH); wild oats (Avenafatua, AVEFA); green foxtail (Setaria viridis, SETVI); morning glory (Ipomoea spp.), multiflorous ryegrass (Lolium perenne L.ssp.multiflorum, LOLMU). The crops tested included corn, wheat, cotton, cowpea and dwarf bean.

[0830] method:

[0831] 2,4-DC (SC 42%) was applied alone or as a combination with sulfentrazone ( 4F, 39.6%) tank mixes of 105, 210 or 315 g ai / ha were applied. Untreated tests were included as reference standards. Palmer amaranth, ragweed, Pennsylvania knotweed, hemp, wild oats, green foxtail, morning glory, and multiflora ryegrass were screened. Corn, wheat, cotton (cotton was not rated due to aphid damage), cowpea and dwarf bean (var. Supremo) were also included in the study. All plants were planted directly in 6x10" fiber flats with Pennington soil. Flats were watered after seeding but before treatment. Flats were placed in the greenhouse and lightly watered after application. Flats were then watered and fertilized daily. Treatments were applied with compressed air in an orbital mist chamber at 30 GPA using a TeeJet 8001E spray head at 40 PSI. Visible percent weed control was recorded at 14, 21 and 28 days after treatment (DAT) and crop injury was recorded at 7, 14, 21 and 28 DAT using a rating of 0 (no control / no injury) to 100 (total plant death). Data (not included) were analyzed using Minitab statistical software with 95% confidence intervals.

[0832] result:

[0833] 2,4-DC applied alone was safe for all crops at all rates at 14 DAT. Sulfonamide alone was safe for corn and dwarf beans only at 105 g, and safe for wheat and cowpea at 105 or 210 g, 14 DAT. Of the 15 combinations of 2,4-DC + sulfonamide, 6 were safe for wheat, 8 were safe for cowpea, and 11 were safe for corn. All tank-mix combinations damaged dwarf beans at 14 DAT. 2,4-DC alone was safe for cowpea at all rates (data not included). Sulfonamide alone damaged both crops at 28 DAT at all rates. Six combinations of tank-mixes of 2,4-DC plus sulfonamide were safe for cowpea, while all combinations damaged dwarf beans. The table below highlights the unexpected safening effect of the tested combinations.

[0834] Crop injury of corn at -21 DAT by 2,4-DC+sulfentrazone

[0835]

[0836] ε-% measurement of crop damage: safe (0-10%); moderate (11-20%); damaged (≥20)

[0837] β and ρ - ratio - g ai / ha

[0838] Example 43: Crop safety of a tank-mix combination of 2,4-DC and pyraclostrobin plus mefenacet-butyl.

[0839] In this example, the crop safety of 2,4DC (alone or in combination with pyraclostrobin plus mefenacet) was analyzed as a pre-emergence treatment on the following weeds: Amaranthus retroflexus (AMARE); Phalaris minor (PHAMI); Cirsium arvense (CIRAR); Dandelion (Taraxacum officinale (TAROF); Green foxtail (Setaria viridis (SETVI); Wild oats (Avena fatua (AVEFA); White clover (Trifolium repens (TRFRE); Yellow sedge (Cyperus esculentus (CYPES); Multiflora ryegrass (Lolium perennespp. multiflorum, LOLMU); Chickweed (Stellaria officinale (TAROF)); Green foxtail (Setaria viridis (SETVI); Wild oats (Avena fatua (AVEFA)); White clover (Trifolium repens (TRFRE); Yellow sedge (Cyperus esculentus (CYPES); Multiflora ryegrass (Lolium perennespp. multiflorum, LOLMU); media, STEME); Elytrigia repens (AGRRE); Field bindweed (Convolvulus arvensis, CONAR). Treatments were applied to rapeseed and wheat.

[0840] result:

[0841] 2,4DC alone was safe (≤10% injury) to canola at ≤200 g ai / ha, and safe to wheat at ≤100 g. 2,4-DC plus pyraclostrobin plus mefenacet was not safe to canola in any tank-mix combination, and 1 tank-mix combination was safe to wheat. Clomazone plus pyraclostrobin plus mefenacet injured both crops. 2,4DC alone offers a safer alternative to the combinations tested.

[0842] Example 44: Crop safety of a tank-mix combination of 2,4-DC and metazachlor plus naproxen.

[0843] In this example, a greenhouse study was conducted to determine the crop selectivity and weed efficacy of 2,4DC (alone or in combination with metazachlor plus naproxen) as a pre-emergence treatment on the following weeds: Amaranth retroflexus (AMARE), Lolium perenne multiflorum (LOLMU), Sinapis arvensis (SINAR), Poa annua (POAAN), Avena fatua (AVEFA), Alopecurus myosuroides (ALOMY), Chenopodium album (CHEAL), Phalaris minor (PHAMI), Stellaria media (STEME), Papaver rhoeas (PAPRH), and Apera longa (AVEFA). spica-venti, APESV). Crops tested included wheat and rapeseed.

[0844] method:

[0845] 2,4-DC (SC 36%) was applied at 50, 100, or 200 g ai / ha alone or as a combination with metazachlor ( 43.1%) and propamide ( 50DF) tank mix. Metazachlor was applied alone or in a tank mix at rates of 250, 500 and 750 g ai / ha, and naproxen was applied at a rate of 1,260 g ai / ha. An untreated test was included as a reference standard. Other treatments included clomazone (

[00136] The treatments were applied prior to germination of Amaranthus retroflexus, Lolium multiflorum, Wild oats, Nigella cumin, Phragmites australis, Chickweed, Chenopodium album, Corn poppy, Wild mustard, Poa annua, Silkweed, Canola, and Wheat. Plants were grown in fiber flats (6"X10") containing Pennington soil and the flats were watered well before and lightly after application. Flats were watered daily and fertilized after application of treatments. Treatments were applied with compressed air in an orbital spray chamber at 30 GPA using a TeeJet 8001E spray head at 40 PSI. Visible percent weed control and visible percent crop injury data were recorded 14, 21 and 28 days after treatment using a rating scale of 0 (no control / no injury) to 100 (complete plant death). Data were analyzed using Minitab statistical software with 95% confidence intervals.

[0846] All combinations of 2,4-DC+metachlor+napropamide caused 100% mortality of Amaranthus retroflexus, Corn Poppy, Multiflora Ryegrass, Bluegrass, Chenopodium album, Small-seeded Phalaenopsis, Chickweed, and Silky Wind Grass. All 9 combinations controlled Nigella sativa. No combination was safe for wheat, and 3 combinations were safe for rapeseed. For example, when 2,4-DC was co-applied with Metachlor+napropamide at the same rate, the damage to rapeseed was reduced to 3%. 2,4DC alone provided control of Corn Poppy at ≥100g, control of Multiflora Ryegrass at ≥200g, control of Chenopodium album at 400g, control of Nigella sativa at ≥200g, control of Silky Wind Grass at ≥100g, and control of Chickweed at all rates.

[0847] In summary, 2,4-DC caused greater than 10% damage to rapeseed at all rates. 2,4DC was safe for wheat up to 200 gai / ha. When 2,4-DC was co-applied with metazachlor + naproxil at the same rate, damage to rapeseed dropped dramatically. All combinations of metazachlor + naproxil provided control of nearly all weeds at all rates and showed no selectivity for rapeseed and wheat. The table below highlights the unexpected safening effect of the tested combinations.

[0848] Example 45: Crop safety of a tank-mix combination of 2,4-DC and mesotrione.

[0849] In this example, the crop safety of 2,4DC was analyzed, either alone or in combination with mesotrione as a pre-emergence treatment of the following weeds: Datura stramonium (DATST), hemp (Abutilontheophrasti, ABUTH), hairy clover (Asteraceae bidens, BIDPA), Pennsylvania cocklebur (Xanthium strumarium, XANST), barnyard grass (Echinochloa crus-galli, ECHCG). Treatments were also applied to sweet corn, yellow corn, and sorghum.

[0850] method:

[0851] 2,4-DC (SC 36%) was applied alone at 50, 100, or 200 g ai / ha or as a tank mix with mesotrione (40%) at 25, 50, or 100 g ai / ha. Untreated tests were included as reference standards. Other treatments included mesotrione plus S-methoxazole (Dual II 82.4%) was applied as a tank mix of 100+525 g, and 2,4-DC was applied alone at 400 g. Treatments were applied before germination of Datura, Hemp, Hairy Clover, Pennsylvania Xanthium, Echinochloa, Sweet Corn, Yellow Corn, and Sorghum. Plants were grown in fiber flats (6"X10") containing Pennington soil, and the flats were well watered before application and lightly watered after application. Flats were watered and fertilized daily after application of treatments. Treatments were applied at 30 GPA with compressed air in an orbital atomization chamber, using a TeeJet8001E nozzle at 40 PSI. Visible percent weed control and visible percent crop injury data were recorded 14, 21, and 28 days after treatment, using a rating of 0 (no control / no injury) to 100 (complete plant death). Data were analyzed using Minitab statistical software with 95% confidence intervals.

[0852] result:

[0853] 2,4-DC alone was safe for sweet corn and sorghum at the lowest rate, and safe for yellow corn at 50 or 100 gai / ha. Mesotrione alone was safe for sweet corn and yellow corn at all 3 rates; it was safe for sorghum at 25 and 50 g. Of the 9 combinations of 2,4-DC + mesotrione, two combinations were safe for sweet corn (≤10%), 5 combinations were safe for sorghum, and 7 combinations were safe for yellow corn.

[0854] Example 46: Safety of 2,4-DC and 2,5-DC on sorghum.

[0855] To compare the tolerance of sorghum before emergence (PRE), 2,4-DC (42% SC), 2,5-DC (47.5%), 4EC (clomazone, 46.7%), and 3ME (clomazone, 31.4%) was applied at 31, 63, 125, 250, and 375 g ai / ha. An untreated test was included as a reference standard. Treatments were applied to sorghum at planting using Pennington soil. Each treatment was replicated 4 times. The soil was watered before and after application for herbicide activation. Plants were watered and fertilized daily. Treatments were applied at 30 GPA using compressed air in an orbital spray chamber using a TeeJet 8001E spray head at 40 PSI. Visible percent crop injury was recorded 7, 14, 21, and 28 days after treatment using a rating of 0 (no injury) to 100 (total plant death). Data were analyzed using Minitab statistical software with 95% confidence intervals.

[0856]

[0857]

[0858] In this study, 2,4-DC and 2,5-DC were safe for sorghum at rates ranging from 31-125 g ai / ha (regardless of grading time) (see table above). At 250 and 375 g, 2,4-DC and 2,5-DC caused injury to sorghum greater than ≥11%. Both formulations of clomazone ( 4EC & 3ME) were safe up to 63g; however, 3ME showed safety at 125g, at 21 and 28 DAT (see table above).

[0859] Example 47: Volatility of Formulations

[0860] A column method was used to determine the volatility of clomazone from moist double-sieve Pennington soil. Clomazone or a clomazone compound (2,4-DC or 2,5-DC) was applied to the soil at 1000 g ai / ha. The amount of clomazone captured from the column was determined over the 18 hour collection period and averaged over 4 replicates in micrograms. The relative volatility compared to the 4EC formulation was determined (average, shown as a percentage). The extracted methanol samples were analyzed using HPLC. The average of these values ​​(4 replicates) was then converted to obtain the total ugs for each treatment.

[0861]

[0862] In this case, microencapsulation provides poor volatility control compared to SC formulations.

[0863] All documents cited herein are incorporated by reference in their entirety.

[0864] Although the present invention has been described with emphasis on preferred embodiments, it will be apparent to those skilled in the art that variations in preferred compositions and methods may be used, and that the present invention may be implemented in ways other than those specifically described herein. Therefore, the present invention includes all changes within the spirit and scope of the invention defined in the appended claims.

Claims

1. A method for pre-emergence control of undesirable vegetation in a crop, comprising applying to the locus of the plant a herbicidally effective amount of a composition, wherein the crop is wheat, and the composition comprises: i. a first herbicide which is 2-(2,4-dichlorophenyl)methyl-4,4-dimethyl-3-isoxazolidinone ("2,4-DC"); and ii. a second herbicide selected from: a) aclonifen, wherein the weight ratio of 2,4-DC: aclonifen is 125:1500, 125:1800, 125:2100, 170:1500, 170:1800, 170:2100, 210:1500, 210:1800, 210:2100, 250:1500, 250:1800 or 250:2100; b) atrazine, wherein the weight ratio of 2,4-DC:atrazine is 50:140, 50:280, 50:560, 100:140, 100:280, 100:560, 200:140, 200:280 or 200:560; c) bromoxynil, wherein the weight ratio of 2,4-DC:bromoxanil is 125:140, 125:210, 125:280, 170:140, 170:210, 170:280, 210:140, 210:210, 210:280, 250:140, 250:210 or 250:280; d) clomazone, wherein the weight ratio of 2,4-DC:clomazone is 125:60, 125:90, 125:120, 170:60, 170:90, 170:120, 210:60, 210:90, 210:120, 250:60, 250:90 or 250:120; e) diflufenicol, wherein the weight ratio of 2,4-DC: diflufenicol is 125:50, 125:75, 125:100, 170:50, 170:75, 170:100, 210:50, 210:75, 210:100, 250:50, 250:75 or 250:100; f) dimethochlor, wherein the weight ratio of 2,4-DC:dimethochlor is 50:333, 50:100, 100:667, 100:100, 200:333, 200:667 or 200:100; g) dimethenamid-P, wherein the weight ratio of 2,4-DC:dimethenamid-P is 125:250, 125:375, 125:500, 170:250, 170:375, 210:250, 210:375, 250:250 or 250:375; h) isoxathiapiprolin, wherein the weight ratio of 2,4-DC:isothiapiprolin is 500:80, 500:100, 500:120, 750:80, 750:100, 750:120, 1000:80, 1000:100 or 1000:120; i) S-methoxazole, wherein the weight ratio of 2,4-DC:S-methoxazole is 125:267, 125:534, 125:801, 125:1070, 170:267, 170:534, 170:801, 170:1070, 210:267, 210:534, 210:801, 210:1070, 250:267, 250:534, 250:801 or 250:1070; j) Metsulfuron-methyl, wherein the weight ratio of 2,4-DC:Metsulfuron-methyl is 50:9, 50:12, 100:6, 100:9, 100:12, 200:6, 200:9 or 200:12; k) napropamide, wherein the weight ratio of 2,4-DC:napropamide is 31:630, 31:1260, 63:315, 63:630, 63:1260, 125:315, 125:630, 125:1260, 250:315, 250:630, 250:1260, 375:315, 375:630 or 375:1260; l) Pirovir, wherein the weight ratio of 2,4-DC:pirovir is 125:50, 125:65, 125:80, 125:95, 170:50, 170:65, 170:80, 170:95, 210:50, 210:65, 210:80, 210:95, 250:50, 250:65, 250:80 or 250:95; m) dimethochlor and metazachlor, wherein the weight ratio of 2,4-DC:dimethochlor:metazachlor is 50:500:375, 50:500:750, 50:1000:750, 100:500:375, 100:1000:375, 100:500:750, 100:1000:750, 200:500:375 or 200:1000:750; and n) pyrochlor and sulfentrazone, wherein the weight ratio of 2,4-DC:pyrochlor:sulfentrazone is 50:30:105, 50:60:105, 50:90:105, 50:30:210, 50:60:210, 50:90:210, 100:30:105, 100:60:105, 100:90:105, 100:30:210, 100:60:210, 200:30:105, 200:90:105, 200:30:210 or 200:60:

210.

2. The method of claim 1, wherein the undesirable plants are selected from the group consisting of wild oats, nightshade, brome, shepherd's purse, quinoa, multiflora ryegrass, bluegrass, chickweed, datura, bamboo leaf vegetable, ragweed, wheatgrass, morning glory, nigella, wild mustard, wild buckwheat, Pennsylvania cocklebur and green hemp.

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