A herbicidal composition containing a cyclohexane-1,3-dione derivative and use thereof

Abstract

The present application relates to the field of pesticides, in particular to a kind of pesticide composition and its application.The herbicidal composition of the present application contains cyclohexane-1,3-diketone derivative shown in formula (I).The pesticide composition of the present application has good effect of preventing and removing farmland weeds, can reduce the amount of drug, reduce the cost of pesticide application, reduce the pollution of pesticide residue to environment.The definition of R1 and R2 is as defined in the specification.

Description

[0001] This application is a divisional application of Chinese Patent Application No. 202211455942.X, filed on November 21, 2022, entitled "A herbicide composition containing cyclohexane-1,3-dione derivative and its application therein". Technical Field

[0002] This invention relates to the field of pesticides, and more specifically, to a herbicide composition containing a cyclohexane-1,3-dione derivative and its application. Background Technology

[0003] Many highly active herbicides do not exhibit good compatibility with beneficial plants, especially dicotyledonous crops such as cotton and rapeseed, as well as gramineous plants such as barley, millet, corn, rice, and wheat. Special combinations of known herbicides can enhance the activity of the herbicidal active ingredient in a synergistic manner. This allows for a reduction in the application rate of the herbicidal active compound required to control harmful plants.

[0004] In addition, in some cases, specific herbicides and some active compounds also possess herbicidal activity, and combined application allows for better crop compatibility. In these cases, the active compound acts as an antidote or antagonist and is also known as a safener.

[0005] Cyclohexane-1,3-dione herbicides are a very important class of herbicides. First developed in the 1960s, these herbicides eliminate weeds by inhibiting acetyl-CoA carboxylase (ACCase), thus disrupting fatty acid biosynthesis. These herbicides are highly effective, safe, and selective ACCase inhibitors, effective only against most annual and perennial grasses, and safe for dicotyledonous crops. Therefore, our company and many other institutions have been dedicated to the research and development of this type of herbicide.

[0006] The applicant disclosed a cyclohexane-1,3-dione compound of formula (I) in CN111205208A, the structural formula of which is:

[0007]

[0008] Wherein, R1 is -CH3, -CH2CH3, -(CH2)2CH3, -CH(CH3)2, -(CH2)3CH3, -CH(CH3)C2H5, -CH2CH(CH3)2 or -C(CH3)3; group R2 is cis-trans-CHCH=CHCl, -CHCCl=CH2 or and The substituent X is selected from -Cl, -F, -NO2 or -CF3, and n is the number of substituent X, which is 1, 2 or 3.

[0009] The applicant's research found that the aforementioned compounds possess excellent herbicidal activity and good safety for related plants. However, long-term use of a single herbicide can easily lead to resistance. During the research process, the applicant discovered that combinations of the aforementioned compounds with relevant herbicides exhibited better weed control effects. Summary of the Invention

[0010] The object of this invention is to provide a herbicidal composition that is highly effective against unwanted harmful plants and has a broad-spectrum herbicidal activity. This and other objects are achieved by the following herbicidal composition.

[0011] The herbicidal composition of the present invention contains a cyclohexane-1,3-dione derivative of formula (I), specifically providing a herbicidal composition comprising A) at least one compound of formula (I): in,

[0012] R1 is -CH3, -CH2CH3, -(CH2)2CH3, -CH(CH3)2, -(CH2)3CH3, -CH(CH3)C2H5, -CH2CH(CH3)2, or -C(CH3)3; the group R2 is cis-trans-CHCH=CHCl, -CHCCl=CH2, or... and The substituent X is selected from -Cl, -F, -NO2 or -CF3, and n is the number of substituent X, which is 1, 2 or 3;

[0013] and / or its agriculturally usable salt;

[0014] And at least one other herbicide-active compound selected from the following:

[0015] B)b1-b9) class herbicides

[0016] b1) Sulfonylurea herbicides, wherein the sulfonylurea herbicides are preferably one or more of the following: pyrimisulfuron, bensulfuron, chlorpyrifos, nicosulfuron, sulfadiazine, mesosulfuron, sulfadiazine, chlorpyrifos, methylsulfuron, flumethrin, and pyrimisulfuron;

[0017] b2) Amide herbicides, wherein the amide herbicides are preferably one or more of the following: metolachlor, acetochlor, isopropylmetolachlor, propachlor, butachlor, ethoxybenzamide, pyrfluthrin, dimethoate, barnyardgrass, isoxachlor, flupyrazole, brobutyrazole, bispyribac-sodium, and propargite.

[0018] b3) Aromatic phenoxypropionic acid herbicides, wherein the aromatic phenoxypropionic acid herbicides are preferably one or more of cyhalofop-butyl, quizalofop-p-ethyl, oxazolidinone, quizalofop-p-ethyl and oxazolidinone;

[0019] b4) Cyclohexenone / triketone herbicides, wherein the cyclohexenone / triketone herbicides are preferably one or more of the following: styraxone, clethodim, pyranoxuron, thiamethoxam, bensulfuron, cyclobensulfuron, clethodim, butyrazosulfuron, quizalofop-p-ethyl, sulfonylsulfuron, cyclosulfonyl ketone, and bicyclosulfonyl ketone.

[0020] b5) Triazolopyrimidine herbicides, wherein the triazolopyrimidine herbicides are preferably one or more of the following: diflubenzuron, methoxysulfuron, pyrazosulfuron, chlorpyrifos-sulfuron, sulfadiazon, and penflubenzuron;

[0021] b6) Pyrimidine salicylic acid herbicides, wherein the pyrimidine salicylic acid herbicides are preferably one or more of pyrimidine sulfide, pyrimidine sulfide, cyclopyrimidine sulfide, bispyribac-sodium and pyrimidine oxime-sodium;

[0022] b7) Carboxylic acid herbicides, preferably one or more of 2,4-D, 2-methyl-4-chloro, 2,4,5-T, 2-methyl-4-chloropropionic acid, 2,4-D isooctyl ester, 2,4,-D butyl ester, dicamba, doxycycline, diquat, and chlorpyrifos;

[0023] b8) Diphenyl ether herbicides, wherein the diphenyl ether herbicides are preferably one or more of flufenoxuron, ethoxyflufenoxuron, quizalofop-p-ethyl, flufenoxuron, and flufenoxuron-methyl.

[0024] b9) Triazine herbicides, wherein the triazine herbicides are preferably one or more of terbufos, isopropylben, fluroxypyr, glycyrrhizin, atrazine, simazine, promethazine, atrazine, cypermethrin, and triazine fluroxypyr.

[0025] The present invention also provides a method for controlling unwanted plant growth, comprising applying the herbicidal composition of the present invention to the plant, its growing environment, or its seeds.

[0026] Beneficial effects of the present invention

[0027] The compositions of the present invention comprising compound (I) and at least one herbicide B have better herbicidal activity than expected based on the herbicidal activity observed on the individual compounds, i.e., better activity against harmful plants and a broader spectrum of activity. Detailed Implementation

[0028] To make the objectives, technical solutions, and advantages of the embodiments of the present invention clearer, the technical solutions in the embodiments of the present invention will be clearly and completely described below. Obviously, the described embodiments are only some embodiments of the present invention, not all embodiments. Based on the embodiments of the present invention, all other embodiments obtained by those skilled in the art without creative effort are within the scope of protection of the present invention. In addition, to better illustrate the present invention, numerous specific details are given in the following detailed embodiments. Those skilled in the art should understand that the present invention can be implemented without certain specific details. In some embodiments, raw materials, excipients, methods, means, etc., well known to those skilled in the art, are not described in detail in order to highlight the main points of the present invention.

[0029] Unless otherwise expressly stated, throughout the specification and claims, the term "comprising" or its variations such as "including" or "comprises" shall be understood to include the stated active ingredient and not to exclude other possible active ingredients.

[0030] In this invention, "control" and "prevention" are synonyms.

[0031] In this invention, "undesirable plant growth" and "harmful plants" are synonyms.

[0032] The compound of formula (I), herbicide B and / or safer C of the present invention can form geometric isomers, such as E / Z isomers, and pure isomers and mixtures thereof can be used in the compositions of the present invention.

[0033] The compounds of formula (I) described in this invention, herbicidal compound B and / or safer agent C have one or more chiral centers and thus exist as enantiomers or diastereomers, so pure enantiomers and diastereomers and mixtures thereof can be used in the compositions of this invention.

[0034] Compounds of formula (I) described herein, herbicidal compound B, and / or safener C, having ionizable functional groups, can also be used in their agronomic salt form. Suitable salts are typically salts of cations whose cations and anions do not adversely affect the activity of the active compound, and acid addition salts of acids.

[0035] Preferred cations are alkali metal ions, preferably lithium, sodium, and potassium ions; alkaline earth metal ions, preferably calcium and magnesium ions; and transition metal ions, preferably manganese, copper, zinc, and iron ions. Additionally, ammonium and substituted ammonium compounds in which 1-4 hydrogen atoms are replaced by C1-C4 alkyl, hydroxy-C1-C4 alkyl, C1-C4 alkoxy-C1-C4 alkyl, hydroxy-C1-C4 alkoxy-C1-C4 alkyl, phenyl, or benzyl groups are preferred. Specifically, ammonium, methylammonium, isopropylammonium, dimethylammonium, diisopropylammonium, trimethylammonium, heptylammonium, dodecylammonium, tetradecylammonium, tetramethylammonium, tetraethylammonium, tetrabutylammonium, 2- Hydroxyethylammonium (alcoholic acid salt), 2-(2-hydroxyethyl-1-oxy)ethyl-1-ylammonium (diethylene glycolamine salt), di(2-hydroxyethyl-1-yl)ammonium (diethylene glycolamine salt), tri(2-hydroxyethyl)ammonium (triethanolamine salt), tri(2-hydroxypropyl)ammonium, benzyltrimethylammonium, benzyltriethylammonium, N,N,N-trimethylethanolammonium (choline salt), and also phosphonium ions, sulfonium ions, preferably tri(C1-C4 alkyl)sulfonium, such as trimethylsulfonium, and sulfonium oxide ions, preferably tri(C1-C4 alkyl)sulfonium oxide, and finally, salts of polyamines such as N,N-di(3-aminopropyl)methylamine and diethylenetriamine.

[0036] The main anions of useful acid addition salts are chloride, bromide, fluoride, iodide, hydrogen sulfate, methyl sulfate, sulfate, dihydrogen phosphate, hydrogen phosphate, nitrate, bicarbonate, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate, and anions of C1-C4 alkanic acids, with formate, acetate, propionate, and butyrate being preferred.

[0037] The endpoints and any values ​​of the ranges disclosed herein are not limited to the precise ranges or values, and these ranges or values ​​should be understood to include values ​​close to these ranges or values. For numerical ranges, the endpoint values ​​of the various ranges, the endpoint values ​​of the various ranges and individual point values, and individual point values ​​can be combined with each other to obtain one or more new numerical ranges, which should be considered as specifically disclosed herein.

[0038] Other embodiments of the invention are apparent from the claims, description, and examples. It should be understood that the features mentioned above and described below can be used not only in the combinations given in each particular case, but also in other combinations, without departing from the scope of the invention.

[0039] The present invention provides a herbicidal composition comprising A) a compound of formula (I): Wherein, R1 is -CH3, -CH2CH3, -(CH2)2CH3, -CH(CH3)2, -(CH2)3CH3, -CH(CH3)C2H5, -CH2CH(CH3)2 or -C(CH3)3; the group R2 is cis-trans-CHCH=CHCl, -CHCCl=CH2 or and The substituent X is selected from -Cl, -F, -NO2 or -CF3, and n is the number of substituent X, which is 1, 2 or 3;

[0040] and / or its agriculturally usable salt;

[0041] And at least one other herbicide-active compound selected from the following:

[0042] B)b1-b9) class herbicides

[0043] b1) Sulfonylurea herbicides, wherein the sulfonylurea herbicides are preferably one or more of pyrimisulfuron, bensulfuron, chlorpyrifos, nicosulfuron, sulfadiazine, mesosulfuron, sulfadiazine, chlorpyrifos, methylsulfuron, flumethrin, and pyrimisulfuron;

[0044] b2) Amide herbicides, wherein the amide herbicides are preferably one or more of the following: metolachlor, acetochlor, isopropylmetolachlor, propachlor, butachlor, ethoxybenzamide, pyrfluthrin, dimethoate, barnyardgrass, isoxachlor, flupyrazole, brobutyrazole, bispyribac-sodium, and propargite.

[0045] b3) Aromatic phenoxypropionic acid herbicides, wherein the aromatic phenoxypropionic acid herbicides are preferably one or more of cyhalofop-butyl, quizalofop-p-ethyl, oxazolidinone, quizalofop-p-ethyl and oxazolidinone;

[0046] b4) Cyclohexenone / triketone herbicides, wherein the cyclohexenone / triketone herbicides are preferably one or more of the following: styraxone, clethodim, pyranoxuron, thiamethoxam, bensulfuron, cyclobensulfuron, clethodim, butyrazosulfuron, quizalofop-p-ethyl, sulfonylsulfuron, cyclosulfonyl ketone, and bicyclosulfonyl ketone.

[0047] b5) Triazolopyrimidine herbicides, wherein the triazolopyrimidine herbicides are preferably one or more of the following: diflubenzuron, methoxysulfuron, pyrazosulfuron, chlorpyrifos, sulfadiazon, and penflubenzuron;

[0048] b6) Pyrimidine salicylic acid herbicides, wherein the pyrimidine salicylic acid herbicides are preferably one or more of pyrimidine sulfide, pyrimidine sulfide, cyclopyrimidine sulfide, bispyribac-sodium and pyrimidine oxime-sodium;

[0049] b7) Carboxylic acid herbicides, preferably one or more of 2,4-D, 2-methyl-4-chloro, 2,4,5-T, 2-methyl-4-chloropropionic acid, 2,4-D isooctyl ester, 2,4,-D butyl ester, dicamba, doxycycline, diquat, and chlorpyrifos;

[0050] b8) Diphenyl ether herbicides, wherein the diphenyl ether herbicides are preferably one or more of flufenoxuron, ethoxyflufenoxuron, quizalofop-p-ethyl, flufenoxuron, and flufenoxuron-methyl.

[0051] b9) Triazine herbicides, wherein the triazine herbicides are preferably one or more of terbufos, isopropylben, fluroxypyr, glycyrrhizin, atrazine, simazine, promethazine, atrazine, cypermethrin, and triazine fluroxypyr.

[0052] In some implementations, preferably, R1 in formula (I) is -CH3, -CH2CH3, or -(CH2)2CH3;

[0053] In some embodiments, preferably, R2 in formula (I) is cis-trans-CHCH=CHCl, -CHCCl=CH2, or... Where X is selected from -Cl, -F, -NO2, and n is 1 or 2.

[0054] In a preferred embodiment, the compound of formula (I) is selected from the following compounds:

[0055] Compound 1: 2-{1-[2-(4-chloro-phenoxy)-propoxyimino]-propyl}-5-(2-ethylthio-propyl)-3-hydroxy-cyclohexyl-2-enone, with the following structural formula:

[0056] Compound 2: 2-{1-[2-(4-chloro-phenoxy)-3-methyl-butoxyimino]-propyl}-5-(2-ethylthio-propyl)-3-hydroxy-cyclohexyl-2-enone, with the following structural formula:

[0057] Compound 3: 2-{1-[2-(3-chloro-allyloxy)-propoxyimino]-propyl}-5-(2-ethylthio-propyl)-3-hydroxy-cyclohexyl-2-enone, with the following structural formula:

[0058] Compound 4: 2-{1-[2-(4-nitro-phenoxy)-propoxyimino]-propyl}-5-(2-ethylthio-propyl)-3-hydroxy-cyclohexyl-2-enone, with the following structural formula:

[0059] Compound 5: 2-{1-[2-(3,5-difluoro-phenoxy)-propoxyimino]-propyl}-5-(2-ethylthio-propyl)-3-hydroxy-cyclohexyl-2-enone, with the following structural formula:

[0060] In a preferred embodiment, preferably, the herbicide B in the composition is selected from one of nicosulfuron, pyrfluthrin, clethodim, bispyribac-sodium, 2,4-D isooctyl ester, atrazine, penoxsulam, oxazolidinyl ester, and cyhalofop-butyl.

[0061] The weight ratio of A to B in the composition is 1:1000-1000:1, preferably 1:100-50:1, and more preferably 1:50-30:1.

[0062] In some embodiments, the composition further includes a safety agent as component C.

[0063] Preferably, the safer component C is selected from one of the following: naphthalene dicarboxylic anhydride, dichloropropyleneamine, benzylamide, furazolidone, oxadiazon, oxadiazon, oxadiazon, oxadiazon, oxadiazon, oxadiazon, oxadiazon, oxadiazon, pyrazosulfuron, bis(oxadiazon), oxadiazon, cyclopropanesulfonamide.

[0064] In a preferred embodiment, the present invention provides a composition containing 2-{1-[2-(4-chloro-phenoxy)-propoxyimino]-propyl}-5-(2-ethylthio-propyl)-3-hydroxy-cyclohex-2-enone (compound 1) and herbicide B, wherein the herbicide B is selected from oxazolidinyl, nicosulfuron, cyhalofop-butyl, and 2,4-D isooctyl ester, and wherein the weight ratio of compound 1 to B is 1:50-50:1, preferably 1:40-40:1.

[0065] In a preferred embodiment, B in the above composition is oxazolidinyl, and the weight ratio of compound 1 to oxazolidinyl is 1:40-40:1, preferably 1:40, 1:30, 1:10, 1:5, 1:2, 1:1, 12:1, or 40:1.

[0066] In a preferred embodiment, B in the above composition is nicosulfuron, and the weight ratio of compound 1 to nicosulfuron is 1:24-7:1, preferably 1:24, 1:6, 1:1, 2:1, or 7:1.

[0067] In a preferred embodiment, B in the above composition is cyhalofop-butyl, and the weight ratio of compound 1 to cyhalofop-butyl is 1:30-20:1, preferably 1:30, 1:15, 1:1, 3:1, 6:1, 10:1 and 20:1.

[0068] In a preferred embodiment, B in the above composition is 2,4-D isooctyl ester, and the weight ratio of compound 1 to 2,4-D isooctyl ester is 1:40-1:5, preferably 1:40, 1:10, or 1:5.

[0069] In a preferred embodiment, the present invention provides a composition comprising 2-{1-[2-(4-chloro-phenoxy)-3-methyl-butoxyimino]-propyl}-5-(2-ethylthio-propyl)-3-hydroxy-cyclohexyl-2-enone (compound 2) and herbicide B, wherein the herbicide is selected from penflusulfonamide and atrazine. The weight ratio of compound 2 to herbicide B is 1:100-15:1.

[0070] In a preferred embodiment, B in the above composition is penoxsulam, and the weight ratio of compound 2 to penoxsulam is 1:20-15:1, preferably 1:20, 1:10, 1:5, 1:1, 2:1, 5:1 and 15:1.

[0071] In a preferred embodiment, B in the above composition is atrazine, and the weight ratio of compound 2 to atrazine is 1:100-1:3, preferably 1:100, 1:60, 1:30, 1:6, or 1:3.

[0072] In a preferred embodiment, the present invention provides a composition containing 2-{1-[2-(3-chloro-allyloxy)-propoxyimino]-propyl}-5-(2-ethylthio-propyl)-3-hydroxy-cyclohex-2-enone (compound 3) and pyrfluthrin, wherein the weight ratio of compound 3 to pyrfluthrin is 1:50-50:1, preferably 1:50, 1:25, 2:5, 1:1, 2:1, 4:1, 10:1, or 50:1.

[0073] In a preferred embodiment, the present invention provides a composition containing 2-{1-[2-(4-nitro-phenoxy)-propoxyimino]-propyl}-5-(2-ethylthio-propyl)-3-hydroxy-cyclohex-2-enone (compound 4) and clethodim, wherein the weight ratio of compound 4 to clethodim is 1:40-40:1, preferably 1:40, 1:10, 1:2, 1:1, 2:1, 3:1, 4:1, 20:1 and 40:1.

[0074] In a preferred embodiment, the present invention provides a composition containing 2-{1-[2-(3,5-difluoro-phenoxy)-propoxyimino]-propyl}-5-(2-ethylthio-propyl)-3-hydroxy-cyclohexyl-2-enone (compound 5) and bispyribac-sodium, wherein the weight ratio of compound 5 to bispyribac-sodium is 1:1 to 12:1, preferably 1:1, 2:1, 4:1, 6:1 and 12:1.

[0075] The present invention also provides a herbicidal composition comprising the composition described above and a suitable pesticide adjuvant.

[0076] Preferably, the active ingredient content in the above-mentioned herbicidal composition is 1-95% by weight; more preferably 1-80% by weight; more preferably 10-55%; even more preferably 30-50%. Within this preferred range, the active ingredient can be rapidly released from the pesticide composition and exert its effect, further improving the control of weeds in the field.

[0077] The types of auxiliary components in the embodiments of the present invention can be selected from a wide range. For example, auxiliary components may include one or more of water, emulsifier, wetting agent, dispersant, thickener, antifreeze, defoamer, binder, disintegrant, organic solvent, solid inert carrier / filler, and stabilizer. Specifically, there may be two, three, four, or five types of auxiliary components.

[0078] For the above-mentioned types of auxiliary ingredients, the specific types of excipients can be selected from a wide range.

[0079] The organic solvent is selected from one or more of the following: benzene, toluene, xylene, naphthalene, naphtha, heavy benzene, methanol, ethanol, cyclohexanone, acetone, vegetable oil, dichloromethane, chloroform, acetonitrile, cresol, ethylene glycol, n-butanol, sorbitol, dimethylformamide, ethyl acetate, and methyl oleate.

[0080] The emulsifier is selected from one or more of the following: octylphenol polyoxyethylene (polyoxypropylene) ether, nonylphenol polyoxyethylene ether, benzylphenol polyoxyethylene ether, phenethylphenol polyoxyethylene ether, fatty alcohol polyoxyethylene ether, fatty acid polyoxyethylene ester, fatty amine polyoxyethylene ether, polyol fatty acid ester, alkylbenzene sulfonate, alkyl sulfonate, agricultural emulsion series, and Tween series. Examples include: calcium dodecylbenzene sulfonate, styrylphenol polyoxyethylene ether phosphate, benzylphenol polyoxyethylene ether phosphate, sorbitan trioleate, glyceryl monostearate, sorbitan monolaurate, polyoxyethylene sorbitan anhydride monolaurate, polyoxyethylene monopalmitate, sorbitan polyoxyethylene ether, polyoxyethylene sorbitan ether monooleate, and castor oil polyoxyethylene ether.

[0081] The dispersant is selected from one or more of the following: alkyl naphthalene sulfonate, naphthalene sulfonate formaldehyde condensate, aralkyl naphthalene sulfonate formaldehyde condensate, naphthol sulfonate formic acid condensate, alkylbenzene sulfonate, alkyl phosphate, alkylphenol polyoxyethylene ether, lignin sulfonate, fatty acid polyoxyethylene ester, fatty amine polyoxyethylene ether, vegetable oil ethylene oxide adduct, ethylene oxide-propylene oxide block copolymer, and ethylenediamine polyoxyethylene polyoxypropylene ether.

[0082] Wetting agents / penetrating agents mainly include one or more of the following: fatty alcohol sulfates, alkylbenzene sulfonates, α-olefin sulfonates, dialkyl succinate sulfonates, fatty amide N-methyl taurate sodium salt, alkyl naphthalene sulfonate sodium salt, etc.

[0083] The thickener is selected from one or more of starch, xanthan gum, agar, methylcellulose, hydroxypropyl methylcellulose, organobentonite, diatomaceous earth, polyvinyl alcohol, magnesium aluminum silicate, clay, and silica.

[0084] The organic suspension medium is selected from one or more of soybean oil, rapeseed oil, corn oil, sunflower oil, cottonseed oil, palm oil, peanut oil, castor oil, and their transesterification products;

[0085] The antifreeze is selected from one or more of ethylene glycol, propylene glycol, glycerin, urea, polyethylene glycol, and sodium chloride;

[0086] The defoamer is selected from polyether defoamers and / or silicone defoamers;

[0087] The binder is selected from one or more of sucrose, maltose, dextrin, and starch;

[0088] The disintegrant is selected from one or more of corn starch, glucose, hydroxypropyl starch, carboxypropyl cellulose, and urea;

[0089] Solid inert carriers / fillers may include one or more of the following: diatomaceous earth, attapulgite, bentonite, sepiolite, kaolin, clay, silica, talc, and light calcium carbonate.

[0090] The preservative is selected from one or more of benzoic acid, sorbic acid, p-hydroxybenzoic acid, hydroquinone, etc.

[0091] The safener is selected from one of the following: naphthalene dicarboxylic anhydride, dichloropropeneamine, benzylamide, furazolidone, oxadiazon, oxadiazon, oxadiazon, oxadiazon, oxadiazon, oxadiazon, oxadiazon, oxadiazon, pyrazosulfuron, bis(oxadiazon), oxadiazon, cyclopropanesulfonamide.

[0092] The herbicidal composition of the present invention can be formulated into various dosage forms, such as suspension concentrates, microcapsule suspension concentrates, emulsifiable concentrates, oil suspension concentrates, microemulsions, water-in-oil emulsions, aqueous solutions, wettable powders, tablet-soluble powders, and water-dispersible granules. These various dosage forms can be prepared using methods known in the art, which will not be elaborated further here.

[0093] Specifically, different auxiliary ingredients can be selected depending on the dosage form.

[0094] The herbicidal composition of the present invention can be provided in the form of a finished product, i.e., the components of the composition have been mixed; or it can be provided in the form of a separate formulation of each component, which can be mixed evenly before use.

[0095] A second aspect of the present invention provides the application of the above-described herbicidal composition in the control of weeds.

[0096] In a preferred embodiment, the weeds are one or more of the following: grasses and broadleaf weeds.

[0097] More preferably, the weeds are barnyard grass, Echinochloa crus-galli, foxtail grass, crabgrass, chickweed, wild oats, goosegrass, barnyard grass, and thistle.

[0098] The present invention also provides a method for controlling unwanted plant growth, comprising applying the herbicidal composition of the present invention to the plant, its growing environment, or its seeds.

[0099] The following provides a detailed description of specific embodiments of the present invention. It should be understood that the specific embodiments described herein are for illustrative and explanatory purposes only and are not intended to limit the invention. Unless otherwise specified, percentage content in the embodiments of the present invention refers to weight percentage. The compound of formula (I) involved in this invention was prepared in our laboratory; the specific preparation method is referenced in CN111205208A. Most of the other compounds and auxiliaries mentioned can be obtained commercially.

[0100] Formulation Examples

[0101] Example 1: 30% Compound 1-oxazolidinyl methyl methacrylate emulsifiable concentrate

[0102] The composition of each group by weight percentage is 15% compound 1, 15% oxazolidinyl acetamiprid, 6% agricultural emulsion 0204, 3% ethanol, and the balance is made up with naphtha.

[0103] Prepare and measure all components, then add most of the naphtha solvent into the mixing vessel, turn on the stirrer, set the stirring speed to 60-80 r / min, add compound 1, oxazolidinyl chlorpyrifos, agricultural emulsion 0204 and ethanol in sequence, then add the remaining naphtha solvent, and stir for 1.5 h to obtain the emulsifiable concentrate.

[0104] Example 2: 11% Compound 2-Pentoxane Dispersible Oil Suspension

[0105] By weight percentage, the proportions of each group are 8% compound 2, 3% penoxsulam, 8% concentrated emulsion 1600, and 2% bentonite, with the balance made up with methyl oleate.

[0106] Prepare the measured components, then add the active ingredient, bentonite, part of agricultural emulsion 1600 and part of methyl oleate to the sand mill in sequence. After 2 hours, stop the sand milling, transfer the mixture to the mixer, add the remaining emulsifier and methyl oleate, and mix evenly.

[0107] Example 3: 75% Compound 3-pyrfluthrin water-dispersible granules

[0108] By weight percentage, the composition of each group is 50% compound 3, 25% pyrfluthrin, 2% clay, 5% sodium dodecyl sulfonate, 3% sodium lignin sulfonate, 1% urea, and starch to make up the balance.

[0109] Prepare the measured components, add the active ingredient, sodium dodecyl sulfonate, sodium lignosulfonate, and clay to water and grind them. After adding urea and starch, transport them to a spray drying tower for spray granulation.

[0110] Example 4: 6% Compound 4-Clethazine Water Emulsion

[0111] The weight percentages of each group are 3% compound 4, 3% clethodim, 10% xylene, 8% concentrated emulsion 500, 2% ethanol, and 3% ethylene glycol, with water to make up the balance.

[0112] Prepare the measured components, mix the active ingredient, xylene, ethanol, and agricultural emulsion 500 evenly, then add ethylene glycol and water, and form an emulsion under high-speed stirring.

[0113] Bioassay

[0114] The test method was conducted in accordance with NY1155.4-2006 Guidelines for Indoor Bioassay of Pesticides. Herbicides. Part 4: Activity Assay. Foliar Spray Method. The specific method is described below.

[0115] Test reagents

[0116] Active ingredient A, cyclohexane-1,3-dione derivative, is produced by our company. Active ingredients B, nicosulfuron, pyrifluquinazon, clethodim, bispyribac-sodium, 2,4-D isooctyl ester, atrazine, penoxsulam, oxazolidinyl ester, and cyhalofop-butyl, are purchased from the market. Weigh a certain amount of the active ingredients, dissolve them in acetone, and dilute them with a 0.1% Tween 80 aqueous solution before use. The specific dosage and ratio of the active ingredients are shown in Table 1-9.

[0117] Weed culture for testing

[0118] Experimental soil: organic matter content 2.5%, pH=6.8; pots: 30cm in diameter, 18cm in height; sowing: fill the pots to 4 / 5 full with soil, and thoroughly moisten the soil by bottom irrigation. Sow 25-30 weed seeds evenly on the soil surface, cover with 1.0cm of soil, and cultivate in a greenhouse at a temperature of 18-25℃; watering method: for paddy field weeds such as barnyard grass, water is added to the top of the pot until saturated; for dryland weeds such as Echinochloa crus-galli, Setaria viridis, Crataegus pinnatifida, Stellaria media, Oat simonii, Eleusine indica, Alopecurus aequalis, and Cirsium japonicum, water is added by bottom irrigation; thinning: after the weeds emerge, thin them out to 10 plants per pot, evenly distributed in the pot.

[0119] Foliar spray treatment:

[0120] At the 3-4 leaf stage of weeds, weeds were treated by foliar spraying in a quantitative automatic spraying device (3WPSH-500E, Nanjing Agricultural Mechanization Research Institute), with a spray volume of 450 L / ha; each treatment was replicated 4 times, and a treatment without active ingredients was set as a blank control.

[0121] Survey Methodology:

[0122] After treatment, the surface of the weeds was allowed to air dry naturally before being transferred to a greenhouse for conventional cultivation. After 14 days, the symptoms of damage and growth inhibition of the tested targets were visually inspected, and the fresh weight of the above-ground portion of the tested target weeds was weighed to calculate the fresh weight inhibition rate (%).

[0123] Fresh weight inhibition rate (%) = (control fresh weight - treatment fresh weight) / control fresh weight × 100.

[0124] Combined action evaluation method: The Gowing method is used to evaluate the combined action of herbicides.

[0125] The formula is: E0=X+Y×(100-X) / 100, where,

[0126] X represents the fresh weight inhibition rate when the dosage of active ingredient A is P;

[0127] Y represents the fresh weight inhibition rate when the dosage of active ingredient B is Q;

[0128] E0 represents the theoretical control efficacy when the dosage of herbicide A is P and the dosage of herbicide B is Q.

[0129] E represents the actual control efficacy of herbicide A and herbicide B when mixed in the above proportions.

[0130] Evaluation criteria: When E-E0 > 10%, it indicates a synergistic effect; when E-E0 is between ±10%, it indicates an additive effect; and when E-E0 < -10%, it indicates an antagonistic effect.

[0131] The specific statistical results are shown in Tables 1-9 below.

[0132] Table 1. Actual control efficacy and combined effect evaluation of compound 1 and oxazolidinone against barnyardgrass, crabgrass, and Echinochloa crus-galli (fresh weight inhibition rate)

[0133]

[0134] Table 2. Actual control efficacy and combined effect evaluation of compound 2 and penoxsulam against barnyardgrass and Echinochloa crus-galli (fresh weight inhibition rate)

[0135]

[0136] Table 3. Actual control efficacy and combined effect evaluation of compound 1 and nicosulfuron against barnyard grass and crabgrass (fresh weight inhibition rate)

[0137]

[0138]

[0139] Table 4. Actual control efficacy of compound 2 and atrazine against barnyardgrass and evaluation of their combined effect (fresh weight inhibition rate)

[0140]

[0141]

[0142] Table 5. Actual control efficacy of compound 3 and pyrfluthrin against chickweed and evaluation of their combined effect (fresh weight inhibition rate)

[0143]

[0144]

[0145] Table 6. Evaluation of the actual control efficacy and combined effect of compound 4 and clethodim against wild oats and goosegrass (fresh weight inhibition rate)

[0146]

[0147]

[0148] Table 7. Actual control efficacy of compound 5 and bispyribac-sodium against barnyardgrass and Alopecurus aequalis, and evaluation of their combined effect (fresh weight inhibition rate).

[0149]

[0150] Table 8. Evaluation of the actual control efficacy and combined effect of Compound 1 and Cyhalofop-butyl against barnyardgrass, crabgrass, Echinochloa crus-galli, and foxtail (fresh weight inhibition rate)

[0151]

[0152]

[0153] Table 9. Evaluation of the actual control efficacy and combined effect of compounds 1 and 2,4-D isooctyl ester against Cirsium japonicum and Stellaria dichotoma (fresh weight inhibition rate)

[0154]

[0155]

[0156] Finally, it should be noted that the above embodiments are only used to illustrate the technical solutions of the present invention, and are not intended to limit them; those skilled in the art should understand that modifications can still be made to the technical solutions described in the foregoing embodiments, or equivalent substitutions can be made to some of the technical features; and these modifications or substitutions do not cause the essence of the corresponding technical solutions to deviate from the spirit and scope of the technical solutions of the embodiments of the present invention.

Claims

1. A herbicidal composition, characterized in that, The herbicidal composition comprises compound A and / or its agriculturally usable salt and herbicide B, wherein compound A is 2-{1-[2-(4-chloro-phenoxy)-3-methyl-butoxyimino]-propyl}-5-(2-ethylthio-propyl)-3-hydroxy-cyclohex-2-enone, and herbicide B is penflusulfonamide or atrazine, wherein the weight ratio of compound A to penflusulfonamide is 1:20-15:1; and the weight ratio of compound A to atrazine is 1:100-1:

3.

2. The herbicidal composition according to claim 1, characterized in that, It also contains a safety agent as component C.

3. The herbicidal composition according to claim 2, characterized in that, The safer component C is selected from one of the following: naphthalene dicarboxylic anhydride, dichloropropeneamine, benzylamide, furazolidone, oxadiazon, oxadiazon, oxadiazon, oxadiazon, oxadiazon, oxadiazon, oxadiazon, oxadiazon, pyrazosulfuron, bis(oxadiazon) acid, quinoline, and cyclopropanesulfonamide.

4. A herbicidal composition comprising the composition according to any one of claims 1-3 and a suitable adjuvant for the pesticide.

5. A method for controlling unwanted plant growth, comprising applying the herbicidal composition of any one of claims 1-4 to the plant, its growing environment, or its seeds.

6. The application of the herbicidal composition according to any one of claims 1-4 in weed control, characterized in that, The weeds mentioned are one or more of the following: grass weeds and broadleaf weeds.

7. The application of the herbicidal composition according to claim 6 in weed control, characterized in that, The weeds are one or more of the following: barnyard grass, Echinochloa crus-galli, foxtail grass, crabgrass, chickweed, wild oats, goosegrass, barnyard grass, and thistle.

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