CN117882722A - Herbicide composition containing cyclohexane-1, 3-dione derivative and application thereof - Google Patents

Herbicide composition containing cyclohexane-1, 3-dione derivative and application thereof Download PDF

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CN117882722A
CN117882722A CN202410042980.5A CN202410042980A CN117882722A CN 117882722 A CN117882722 A CN 117882722A CN 202410042980 A CN202410042980 A CN 202410042980A CN 117882722 A CN117882722 A CN 117882722A
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Prior art keywords
compound
weeds
herbicidal composition
herbicide
propyl
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Inventor
邓照西
杨莉娜
李志军
岑金
胡合伟
郭少雄
杜兵兵
黄帅
李君沛
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Zhengzhou Institute Of Chiral Drugs Research Co ltd
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Zhengzhou Institute Of Chiral Drugs Research Co ltd
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Abstract

The invention relates to the field of pesticides, in particular to a pesticide composition and application thereof. The herbicidal composition of the present invention contains a cyclohexane-1, 3-dione derivative represented by formula (I). The pesticide composition has good effect of preventing and killing farmland weeds, can reduce the dosage, reduce the pesticide application cost and reduce the pollution of pesticide residues to the environment.Wherein R is 1 And R is 2 The definition of (a) is defined in the specification.

Description

Herbicide composition containing cyclohexane-1, 3-dione derivative and application thereof
The present application is filed on 11/21 2022 and is a divisional application of chinese patent application 202211455942.X entitled "herbicide composition containing cyclohexane-1, 3-dione derivatives and use thereof".
Technical Field
The invention relates to the field of pesticides, in particular to a herbicide composition containing cyclohexane-1, 3-dione derivatives and application thereof.
Background
For many highly active herbicides, they are not very compatible with useful plants, especially dicotyledonous crops, such as cotton, oilseed rape, and grasses, such as barley, millet, maize, rice, wheat, etc. The specific combination of different known specific herbicides can increase the activity of the active ingredients of the herbicide in a synergistic sense. In this way, the application rate of the herbicidally active compounds required for controlling the harmful plants can be reduced.
In addition, in some cases specific herbicides have herbicidal activity with some of the active compounds, the combined application allowing better crop compatibility. In these cases, the active compounds act as antidotes or antagonists and are also referred to as safeners.
Cyclohexane-1, 3-dione herbicides, which were developed in the early 60 s of the 20 th century, destroy fatty acid biosynthesis by inhibiting acetyl-coa carboxylase (ACCase) to remove weeds, are a very important class of herbicides. The herbicide is an ACCase inhibitor with high efficiency, safety and high selectivity, has special effect on most annual and perennial grassy weeds and is safe for dicotyledonous crops, and therefore, the enterprises and a plurality of institutions are constantly striving to develop the herbicide.
The applicant discloses in CN111205208A cyclohexane-1, 3-dione compound represented by formula (I), which has the structural formula:
wherein R is 1 is-CH 3 、-CH 2 CH 3 、-(CH 2 ) 2 CH 3 、-CH(CH 3 ) 2 、-(CH 2 ) 3 CH 3 、-CH(CH 3 )C 2 H 5 、-CH 2 CH(CH 3 ) 2 or-C (CH) 3 ) 3 The method comprises the steps of carrying out a first treatment on the surface of the Group R 2 For cis-trans-chch=chcl, -chccl=ch 2 Or (b)And->Wherein the substituent X is selected from-Cl, -F, -NO 2 or-CF 3 N is the number of substituents X, 1, 2 or 3.
The research of the applicant finds that the compound has excellent herbicidal activity and better safety on related plants. However, resistance is easily developed by long-term use of a single herbicide. The applicant finds that the combination of the compound and related herbicide shows better weeding effect in the research process.
Disclosure of Invention
The object of the present invention is to provide a herbicidal composition which is highly effective against unwanted harmful plants, and which has a comparatively broad herbicidal activity. This and other objects are achieved by the following herbicidal compositions.
The herbicidal composition of the present invention comprises a cyclohexane-1, 3-dione derivative represented by the formula (I), and specifically provides a herbicidal composition comprisingThe herbicidal composition comprises A) at least one compound of formula (I):wherein,
R 1 is-CH 3 、-CH 2 CH 3 、-(CH2) 2 CH 3 、-CH(CH 3 ) 2 、-(CH 2 ) 3 CH 3 、-CH(CH 3 )C 2 H 5 、-CH 2 CH(CH 3 ) 2 or-C (CH) 3 ) 3 The method comprises the steps of carrying out a first treatment on the surface of the Group R 2 For cis-trans-chch=chcl, -chccl=ch 2 Or (b)And->Wherein the substituent X is selected from-Cl, -F, -NO 2 or-CF 3 N is the number of substituent groups X and is 1, 2 or 3;
and/or an agriculturally acceptable salt thereof;
and at least one further herbicide active compound selected from the group consisting of:
b) b1-b 9) herbicides
b1 Sulfonylurea herbicides, preferably one or more of pyrazosulfuron-ethyl, bensulfuron-methyl, halosulfuron-methyl, nicosulfuron, rimsulfuron-methyl, mesosulfuron-methyl, primisulfuron-methyl, flucarbazone-methyl and flazasulfuron-methyl;
b2 Amide herbicides, preferably one or more of alachlor, acetochlor, metolachlor, pretilachlor, butachlor, acetochlor, diflufenican, dithiachlor, barnyard grass, clomazone, fluopicolide, bromobutachlor, biszoxamide and propanil;
b3 An aryloxyphenoxypropionic acid herbicide, preferably one or more of cyhalofop-butyl, quizalofop-p-ethyl, metamifop, fenoxaprop-p-ethyl and oxadiazon;
b4 Cyclohexenone/trione herbicides, preferably one or more of triclosan, sethoxydim, pyrone, thioxanthone, phenone, cycloxaprine, clethodim, fenpropione, graminetin, sulcotrione, mesotrione, cyclosulfamuron and bicyclosultone;
b5 Triazolopyrimidine herbicides, preferably one or more of florasulam, methoxam, flumetsulam, cloransulam, sulfentrazone, penoxsulam;
b6 Pyrimidine salicylic acid herbicides, preferably one or more of pyrithiobac-sodium, pyriminobac-methyl, pyriftalid and pyriftalid;
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, leguminous, dichlorvos and picloram;
b8 Diphenyl ether herbicides, preferably one or more of fomesafen, fluoroglycofen-ethyl, oxyfluorfen, lactofen, fluroxypyr-meptyl and trifloxystrobin;
b9 A triazobenzene herbicide, preferably one or more of terbutryn, ipratropium, fipronil, glycyrrhizin, ametryn, simazine, prometryn, atrazine, simetryn and triazoxamide.
The present invention also provides a method of controlling the growth of undesirable vegetation which comprises applying to the vegetation, the environment in which it is growing, or the seed thereof the herbicidal compositions of the present invention.
The beneficial effects of the invention are that
The compositions of the invention comprising a compound of formula (I) and at least one herbicide B have better herbicidal activity, i.e. better activity and a broader spectrum of activity on harmful plants than would be expected based on the herbicidal activity observed for the compounds alone.
Detailed Description
For the purpose of making the objects, technical solutions and advantages of the embodiments of the present invention more apparent, the technical solutions in the embodiments of the present invention will be clearly and completely described below, and it is apparent that the described embodiments are some embodiments of the present invention, but not all embodiments. All other embodiments, which can be made by those skilled in the art based on the embodiments of the invention without making any inventive effort, are intended to be within the scope of the invention. In addition, numerous specific details are set forth in the following description in order to provide a better illustration of the invention. It will be understood by those skilled in the art that the present invention may be practiced without some of these specific details. In some embodiments, raw materials, auxiliary materials, methods, means, etc. well known to those skilled in the art are not described in detail in order to highlight the gist of the present invention.
Throughout the specification and claims, unless explicitly stated otherwise, the term "comprise" or variations thereof such as "comprises" or "comprising" and the like will be understood to include the stated active ingredient without excluding other active ingredients that may be present.
In the present invention, "control" and "control" are synonymous.
"undesired plant growth" and "harmful plants" are synonymous in the present invention.
The compounds of formula (I), herbicide B and/or safener C according to the invention are capable of forming geometric isomers, for example E/Z isomers, it being possible to use pure isomers and mixtures of both in the compositions according to the invention.
The compounds of the formula (I), herbicidal compounds B and/or safeners C described in the present invention have one or more chiral centers and are therefore present as enantiomers or diastereomers, it being possible to use the pure enantiomers and diastereomers and mixtures thereof in the compositions according to the invention.
The compounds of the formula (I), herbicidal compounds B and/or safeners C described herein have ionizable functional groups, they can also be used in the form of their agriculturally acceptable salts. Suitable are generally the salts of those cations and the acid addition salts of those acids, the cations and anions of which, respectively, do not adversely affect the activity of the active compound.
Preferred cations are ions of alkali metals, preferably lithium, sodium and potassium ions, alkaline earth metals, preferably calcium and magnesium ions, and transition metals, preferably manganese, copper, zinc and iron ions, furthermore ammonium and substituted ammonium in which 1 to 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, preference is given to ammonium, methylammonium, isopropylammonium, dimethylammonium, diisopropylammonium, trimethylammonium, heptylammonium, dodecylammonium, tetradecylammonium, tetramethylammonium, tetraethylammonium, tetrabutylammonium, 2-hydroxyethylammonium (alcohol amine salt), 2- (2-hydroxyethan-1-yloxy) ethan-1-ylammonium (diglycolamine salt), di (2-hydroxyethan-1-yl) ammonium (glycol amine salt), tri (2-hydroxyethyl) ammonium (triolamine salt), tri (2-hydroxypropyl) ammonium, benzyltrimethylammonium, benzyltriethylammonium, N, N, N-trimethylethanolamine (choline salt), in addition to phosphonium ions, sulfonium ions, preferably tri (C1-C4-alkyl) sulfonium, such as trimethylsulfonium, and sulfoxonium ions, preferably tri (C1-C4-alkyl) sulfoxonium, and finally also polyamines such as N, N-di (3-aminopropyl) methylamine and salts of diethylenetriamine.
Anions of useful acid addition salts are mainly chloride, bromide, fluoride, iodide, bisulfate, methylsulfate, sulfate, dihydrogen phosphate, hydrogen phosphate, nitrate, hydrogen carbonate, hexafluorosilicate, hexafluorophosphate, benzoate and also anions of C1-C4 alkanoic acids, preferably formate, acetate, propionate and butyrate.
The endpoints and any values of the ranges disclosed herein are not limited to the precise range or value, and are understood to encompass values approaching those ranges or values. For numerical ranges, one or more new numerical ranges may be found between the endpoints of each range, between the endpoint of each range and the individual point value, and between the individual point value, in combination with each other, and are to be considered as specifically disclosed herein.
Other embodiments of the invention are apparent from the claims, specification and examples. It is to be understood that the features of the inventive subject matter which are mentioned above and yet to be explained below can be used not only in the combination given in each particular case but also in other combinations without departing from the scope of the invention.
In one aspect, the present invention provides a herbicidal composition comprising a) a compound of formula (I):wherein R is 1 is-CH 3 、-CH 2 CH 3 、-(CH 2 ) 2 CH 3 、-CH(CH 3 ) 2 、-(CH 2 ) 3 CH 3 、-CH(CH 3 )C 2 H 5 、-CH 2 CH(CH 3 ) 2 or-C (CH) 3 ) 3 The method comprises the steps of carrying out a first treatment on the surface of the Group R 2 For cis-trans-chch=chcl, -chccl=ch 2 Or (b)And->Wherein the substituent X is selected from-Cl, -F, -NO 2 or-CF 3 N is the number of substituent groups X and is 1, 2 or 3;
and/or an agriculturally acceptable salt thereof;
and at least one further herbicidally active compound selected from the group consisting of:
b) b1-b 9) herbicides
b1 Sulfonylurea herbicides, preferably one or more of pyrazosulfuron-ethyl, bensulfuron-methyl, halosulfuron-methyl, nicosulfuron, rimsulfuron-methyl, mesosulfuron-methyl, amidosulfuron-methyl, halosulfuron-methyl and flazasulfuron-methyl;
b2 Amide herbicides, preferably one or more of alachlor, acetochlor, metolachlor, pretilachlor, butachlor, acetochlor, diflufenican, dithiachlor, barnyard grass, clomazone, fluopicolide, bromobutachlor, biszoxamide and propanil;
b3 An aryloxyphenoxypropionic acid herbicide, preferably one or more of cyhalofop-butyl, quizalofop-p-ethyl, metamifop, fenoxaprop-p-ethyl and oxadiazon;
b4 Cyclohexenone/trione herbicides, preferably one or more of triclosan, sethoxydim, pyrone, thioxanthone, phenone, cycloxaprine, clethodim, fenpropione, graminetin, sulcotrione, mesotrione, cyclosulfamuron and bicyclosultone;
b5 Triazolopyrimidine herbicides, preferably one or more of florasulam, methoxam, flumetsulam, cloransulam, sulfentrazone-ethyl and penoxsulam;
b6 Pyrimidine salicylic acid herbicides, preferably one or more of pyrithiobac-sodium, pyriminobac-methyl, pyriftalid and pyriftalid;
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, leguminous, dichlorvos and picloram;
b8 Diphenyl ether herbicides, preferably one or more of fomesafen, fluoroglycofen-ethyl, oxyfluorfen, lactofen, fluroxypyr-meptyl and trifloxystrobin;
b9 A triazobenzene herbicide, preferably one or more of terbutryn, ipratropium, fipronil, glycyrrhizin, ametryn, simazine, prometryn, atrazine, simetryn and triazoxamide.
In some embodiments, preferably, R in formula (I) 1 is-CH 3 、-CH 2 CH 3 、-(CH 2 ) 2 CH 3 ；
In some embodiments, preferably, R in formula (I) 2 For cis-trans-chch=chcl, -chccl=ch 2 Or (b)Wherein X is selected from-Cl, -F, -NO 2 N is 1 or 2.
In a preferred embodiment, the compound of formula (I) is selected from the following compounds:
compound 1:2- {1- [2- (4-chloro-phenoxy) -propoxyimino]-propyl } -5- (2-ethylsulfanyl-propyl) -3-hydroxy-cyclohex-2-enone having the structural formula:
compound 2:2- {1- [2- (4-chloro-phenoxy) -3-methyl-butoxyimino group]-propyl } -5- (2-ethylsulfanyl-propyl) -3-hydroxy-cyclohex-2-enone having the structural formula:
compound 3:2- {1- [2- (3-chloro-allyloxy) -propoxyiminol]-propyl } -5- (2-ethylsulfanyl-propyl) -3-hydroxy-cyclohex-2-enone having the structural formula:
compound 4:2- {1- [2- (4-nitro-phenoxy) -propoxyimino]-propyl } -5- (2-ethylsulfanyl-propyl) -3-hydroxy-cyclohex-2-enone having the structural formula:
compound 5:2- {1- [2- (3, 5-difluoro-phenoxy) -propoxyimino]-propyl } -5- (2-ethylsulfanyl-propyl) -3-hydroxy-cyclohex-2-enone having the structural formula:
in a preferred embodiment, the herbicide B in the composition is preferably selected from one of nicosulfuron, diflufenican, clethodim, bispyribac-sodium, 2, 4-isooctyl-d, atrazine, penoxsulam, oxazoxamide and cyhalofop-butyl.
Wherein the weight ratio of A to B in the composition is 1:1000-1000:1, preferably 1:100-50:1, more preferably 1:50-30:1.
in some embodiments, further, a safener is additionally included in the above composition as component C.
Preferably, the safener C component is selected from one of naphthalene dicarboxylic anhydride, dichloropropylamine, benzalkonium amide, furbenoxamide, clomazone, benoxacor, benoxanil, oryzalin, benoxaden, benoxamidine, benoxazamate, mezopyr-diethyl, bisbenzoxazole acid, cloquintocet-mexyl and cyclopropanesulfonamide.
In a preferred embodiment, the present invention provides a composition comprising 2- {1- [2- (4-chloro-phenoxy) -propoxyimino ] -propyl } -5- (2-ethylsulfanyl-propyl) -3-hydroxy-cyclohex-2-enone (compound 1) and herbicide B, wherein the herbicide B is selected from the group consisting of metamifop, nicosulfuron, cyhalofop-butyl, 2, 4-isooctyl ester, wherein the weight ratio of compounds 1 and B is 1:50-50:1, preferably 1:40-40:1.
in a preferred embodiment, in the composition, B is metamifop, and the weight ratio of the compound 1 to metamifop is 1:40-40:1, preferably 1:40, 1:30, 1:10, 1:5, 1:2, 1:1, 12:1, 40:1.
In a preferred embodiment, in the composition, B is nicosulfuron, and the weight ratio of the compound 1 to nicosulfuron is 1:24-7:1, preferably 1:24, 1:6, 1:1, 2:1, 7:1.
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.
In a preferred embodiment, B in the above composition is 2, 4-isooctyl-dride, the weight ratio of compound 1 to 2, 4-isooctyl-dride being 1:40-1:5, preferably 1:40, 1:10, 1:5.
In a preferred embodiment, the present invention provides a composition comprising 2- {1- [2- (4-chloro-phenoxy) -3-methyl-butoxyimino ] -propyl } -5- (2-ethylsulfanyl-propyl) -3-hydroxy-cyclohex-2-enone (compound 2) and herbicide B, wherein the herbicide is selected from penoxsulam, atrazine. Wherein the weight ratio of the compound 2 to the herbicide B is 1:100-15:1.
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.
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. 1:3.
in a preferred embodiment, the present invention provides a composition comprising 2- {1- [2- (3-chloro-allyloxy) -propoxyimino ] -propyl } -5- (2-ethylsulfanyl-propyl) -3-hydroxy-cyclohex-2-enone (compound 3) and diflufenican, wherein the weight ratio of compound 3 to diflufenican is 1:50-50:1, preferably 1:50, 1:25, 2: 5. 1: 1. 2:1. 4: 1. 10:1, 50:1.
In a preferred embodiment, the present invention provides a composition comprising 2- {1- [2- (4-nitro-phenoxy) -propoxyimino ] -propyl } -5- (2-ethylsulfanyl-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.
In a preferred embodiment, the present invention provides a composition comprising 2- {1- [2- (3, 5-difluoro-phenoxy) -propoxyimino ] -propyl } -5- (2-ethylsulfanyl-propyl) -3-hydroxy-cyclohex-2-enone (compound 5) and bispyribac-sodium, wherein the weight ratio of compound 5 to bispyribac-sodium is 1:1-12:1, preferably 1: 1. 2:1. 4: 1. 6:1 and 12:1.
the invention also provides a weeding composition, which comprises the composition and a pesticide proper auxiliary agent.
Preferably, in the herbicidal composition, the content of the active ingredient is 1 to 95% by weight; preferably 1 to 80% by weight; more preferably 10 to 55%, still more preferably 30 to 50%, in which the active ingredient can be rapidly released from the pesticidal composition and functions, further improving the control of weeds in the field.
The types of the auxiliary components in the embodiment of the present invention may be selected within a wide range, and for example, the auxiliary components may include one or more of water, an emulsifier, a wetting agent, a dispersing agent, a thickener, an antifreezing agent, an antifoaming agent, a binder, a disintegrant, an organic solvent, a solid inert carrier/filler, and a stabilizer, and the plurality may be specifically two, three, four, or five.
For the above auxiliary components of each type, the specific auxiliary materials can be selected in a wide range.
The organic solvent is selected from one or more of 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;
the emulsifier is selected from octyl phenol polyoxyethylene (polyoxypropylene) ether, nonylphenol polyoxyethylene ether, benzyl phenol polyoxyethylene ether, phenethyl phenol polyoxyethylene ether, fatty alcohol polyoxyethylene ether, fatty acid polyoxyethylene ester, fatty amine polyoxyethylene ether, polyalcohol fatty acid ester, alkylbenzene sulfonate, alkyl sulfonate, pesticide emulsion series and tween series. For example: one or more of calcium dodecylbenzenesulfonate, styrylphenol polyoxyethylene ether phosphate, benzyl phenol polyoxyethylene ether phosphate, sorbitan trioleate, glycerol monostearate, sorbitan monolaurate, polyoxyethylene monopalmitate, sorbitan polyoxyethylene ether, polyoxyethylene sorbitan ether monooleate, and castor oil polyoxyethylene ether;
the dispersing agent is one or more selected from alkyl naphthalene sulfonate, naphthalene sulfonate formaldehyde condensate, aralkyl naphthalene sulfonate formaldehyde condensate, naphthol sulfonic 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;
the wetting agent/penetrating agent mainly comprises one or more of fatty alcohol sulfate, alkylbenzene sulfonate, alpha-olefin sulfonate, dialkyl succinate sulfonate, fatty amide N-methyl taurate sodium salt, alkyl naphthalene sulfonate and the like;
the thickener is one or more selected from starch, xanthan gum, agar, methylcellulose, hydroxypropyl methylcellulose, organic bentonite, diatomite, polyvinyl alcohol, aluminum magnesium silicate, clay and white carbon black;
the organic suspending 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 transesterification products thereof;
the antifreezing agent is one or more selected from ethylene glycol, propylene glycol, glycerol, urea, polyethylene glycol and sodium chloride;
the defoamer is selected from polyether defoamer and/or organosilicon defoamer;
the binder is selected from one or more of sucrose, maltose, dextrin and starch;
the disintegrating agent is one or more selected from corn starch, glucose, hydroxypropyl starch, carboxypropyl cellulose and urea;
the solid inert carrier/filler may include one or more of diatomaceous earth, attapulgite, bentonite, sepiolite, kaolin, china clay, white carbon, talc and light calcium;
the preservative is selected from one or more of benzoic acid, sorbic acid, parahydroxybenzoic acid, hydroquinone and the like;
the safener is selected from one of naphthalene dicarboxylic anhydride, dichloropropylamine, benzalkonium amide, furbenoxazal, clomazone, benoxaden, benoxanil, oryzalin, benoxaden, mebendazole, mefenacet, bisbenzoxazole acid, cloquintocet-mexyl and cyclopropanesulfonamide.
The weeding composition can be prepared into various dosage forms, for example, can be one of suspending agents, microcapsule suspending agents, emulsifiable concentrates, oil suspending agents, microemulsions, aqueous emulsions, aqueous agents, wettable powder, tablet soluble powder and water dispersible granules. The various dosage forms described above may be prepared using methods well known in the art and will not be described in detail herein.
Specifically, different auxiliary components can be selected according to different dosage forms.
The herbicidal compositions of the present invention may be provided in finished form, i.e. the ingredients of the composition have been mixed; or providing each component in the form of individual preparation, and mixing well before use.
A second aspect of embodiments of the present invention provides the use of the herbicidal composition described above for controlling weeds.
Preferably, the weeds are one or more than two of grassy weeds and broadleaf weeds.
More preferably, the weeds are barnyard grass, moleplant seed, green bristlegrass, crabgrass, chickweed, wild oat, goosegrass, alopecuroide, and field thistle.
The present invention also provides a method of controlling unwanted plant growth comprising applying the herbicidal composition of the present invention to a plant, the environment in which it is grown or seeds thereof.
The following describes specific embodiments of the present invention in detail. It should be understood that the detailed description and specific examples, while indicating and illustrating the invention, are not intended to limit the invention. The percentages in the examples of the present invention refer to weight percentages unless otherwise specified. The compounds of formula (I) to which the invention relates are prepared by the laboratory of the company, the specific preparation method is referred to CN111205208A, and most of the compounds and auxiliaries mentioned are available on the market.
Formulation examples
EXAMPLE 1 30% Compound 1 metamifop emulsifiable concentrate
The weight percentage of each component is 15% of compound 1, 15% of oxazoxamide, 6% of agro-emulsion 0204, 3% of ethanol and the balance of naphtha.
Preparing and metering all components, adding most of naphtha solvent into a preparation kettle, opening stirring, setting stirring speed to be 60-80 r/min, sequentially adding the compound 1, the oxazoxamide, the agro-emulsion 0204 and the ethanol, then adding the rest of naphtha solvent, and stirring for 1.5h to obtain the emulsifiable concentrate.
EXAMPLE 2 11% Compound 2 penoxsulam dispersible oil suspension
The weight percentages of the components are 8% of compound 2, 3% of penoxsulam, 8% of concentrated milk 1600 and 2% of bentonite, and the balance is complemented by methyl oleate.
The components which are well metered are prepared, then the active ingredients, bentonite, part of the agricultural emulsion 1600 and part of methyl oleate are sequentially added into a sand mill, sand milling is stopped after 2 hours, the mixture is conveyed into a mixer, and the rest of the emulsifying agent and the methyl oleate are added and uniformly mixed.
Example 3 75% Compound 3 diflufenican Water dispersible granule
The weight percentage of each component is 50 percent of compound 3, 25 percent of diflufenican, 2 percent of clay, 5 percent of sodium dodecyl sulfate, 3 percent of sodium lignin sulfonate, 1 percent of urea and the balance of starch.
The components which are well metered are prepared, active ingredients, sodium dodecyl sulfate, sodium lignin sulfonate and clay are added into water for grinding, urea and starch are added, and then the mixture is conveyed to a spray drying tower for spray granulation.
Example 4 6% Compound 4 clethodim aqueous emulsion
The weight percentages of the components are 3% of compound 4, 3% of clethodim, 10% of dimethylbenzene, 8% of concentrated milk 500, 2% of ethanol and 3% of glycol, and the balance is water.
The components are prepared to be metered, active ingredients, dimethylbenzene, ethanol and agricultural emulsion 500 are uniformly mixed, then ethylene glycol and water are added, and an aqueous emulsion is formed under high-speed stirring.
Bioassays
The measurement method was carried out by the stem and leaf spray method according to the indoor bioassay test standard of agricultural chemicals NY1155.4-2006, the herbicide, the activity test of the 4 th portion, and the specific method as follows.
Test agent
The active ingredient A cyclohexane-1, 3-dione derivative is produced by the company, the active ingredient B nicosulfuron, diflufenican, clethodim, bispyribac-sodium, 2, 4-isooctyl, atrazine, penoxsulam, oxazoxamide and cyhalofop-butyl are purchased from the market, a certain amount of the active ingredient A is weighed and dissolved by using acetone as a solvent, and the active ingredient B is diluted by using 0.1% Tween 80 aqueous solution, wherein the specific use amount and the specific proportion of the active ingredient are shown in tables 1-9.
Weed culture for test
Experimental soil: organic matter content 2.5%, ph=6.8, bowl: pot with diameter of 30cm and height of 18cm, sowing: the soil is filled at 4/5 of the pot, the soil is completely wetted by adopting a infiltrating irrigation mode at the bottom of the pot, 25-30 weed seeds are uniformly sown on the surface of the soil, the soil is covered by 1.0cm, and the culture temperature is as follows: 18-25 ℃; watering mode: the paddy field weeds such as barnyard grass are irrigated to be saturated by a pot top irrigation mode, and the dry field weeds such as moleplant seed, green bristlegrass, crabgrass, chickweed, wild oat, goosegrass, alopecuroide and herba Cephalanoploris are irrigated by a pot bottom infiltrating mode; thinning: and after the weeds are planted, thinning and setting are carried out, 10 plants of weeds are reserved in each pot, and the weeds are uniformly distributed in the pot.
Stem and leaf spraying treatment:
in the 3-4 leaf stage of weeds, in a quantitative automatic spraying device (3 WPSH-500E, nanjing agricultural mechanization institute), the weeds are treated by adopting a stem and leaf spraying mode, and the spraying amount is calculated according to 450L/ha; each treatment was set up with 4 replicates and treatments without active ingredient were set up as blank.
The investigation method comprises the following steps:
and naturally air-drying the liquid medicine on the surface of the weeds after treatment, moving to a greenhouse for conventional culture, visually inspecting the victim symptoms and growth inhibition conditions of the tested targets after 14 days, weighing the fresh weight of overground parts of the weeds of the tested targets, and calculating the fresh weight inhibition rate (%).
Fresh weight inhibition (%) = (control fresh weight-treated fresh weight)/control fresh weight x 100.
Combined action evaluation method: the mode of action of the herbicide combination was evaluated according to the Gowing method,
the formula is as follows: e (E) 0 =x+y× (100-X)/100, wherein,
x is the fresh weight inhibition rate when the dosage of the active ingredient A is P;
y is the fresh weight inhibition rate when the dosage of the active component B is Q;
E 0 the herbicide is a theoretical control effect when the dosage of the herbicide A is P+ and the dosage of the herbicide B is Q;
e is the actual control effect of the herbicide A and the herbicide B after being mixed according to the proportion.
Evaluation criteria: when E-E 0 >Expressed as synergy at 10%, when E-E 0 Between 10% and E-E 0 <-10% expressed as antagonism.
The specific statistical results are shown in tables 1-9 below.
TABLE 1 evaluation of actual control of Carpesium, crab grass and Euphorbia lathyris by Compound 1 and oxazachlor (fresh weight inhibition)
TABLE 2 evaluation of actual control of barnyard grass and Euphorbia lathyris by Compound 2 and penoxsulam and their Combined action (fresh weight inhibition)
TABLE 3 evaluation of actual control of Echinocaulis and crabgrass by Compound 1 and nicosulfuron and their Combined action (fresh weight inhibition)
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TABLE 4 evaluation of actual control of crabgrass and barnyard grass by Compound 2 and atrazine in combination (fresh weight inhibition)
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TABLE 5 evaluation of actual control of chickweed and Co-action of Compound 3 and diflufenican (fresh weight inhibition)
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TABLE 6 evaluation of actual control of wild oat, nigella sativa and Co-action of Compound 4 and clethodim (fresh weight inhibition)
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TABLE 7 evaluation of actual control of barnyard grass, myrtle and Co-action of Compound 5 and Bispyribac-sodium (fresh weight inhibition)
TABLE 8 evaluation of actual control of and combined action of Compound 1 and cyhalofop-butyl on barnyard grass, crab grass, euphorbia lathyris and green bristlegrass (fresh weight inhibition)
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TABLE 9 evaluation of actual control of Compound 1 and 2, 4-Diisooctyl ester on Cephalanoploris, chickweed and Combined action (fresh weight inhibition)
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Finally, it should be noted that: the above embodiments are only for illustrating the technical solution of the present invention, and are not limiting; those of ordinary skill in the art will appreciate that: the technical scheme described in the foregoing embodiments can be modified or some technical features thereof can be replaced by equivalents; such modifications and substitutions do not depart from the spirit and scope of the technical solutions of the embodiments of the present invention.

Claims (7)

1. A herbicidal composition, characterized in that it comprises compound a and/or an agriculturally acceptable salt thereof; and at least one other herbicidally active compound B selected from the group consisting of 2- {1- [2- (3, 5-difluoro-phenoxy) -propoxyimino ] -propyl } -5- (2-ethylsulfanyl-propyl) -3-hydroxy-cyclohex-2-enone, said herbicide B being bispyribac-sodium, the weight ratio of compound a to bispyribac-sodium being 1:1-12:1.
2. the herbicidal composition of claim 1 additionally comprising a safener as component C.
3. The herbicidal composition of claim 2 wherein safener C component is selected from one of naphthalene dicarboxylic anhydride, dichloropropylamine, benzamides, furbenoxaden, benoxadone, benoxacor, benoxazen, oxadiazon, benoxaden, benoxaziclomefone, mefenacet, mefenoxam, mefenacet, diphenoxazole acid, cloquintocet-mexyl, and cyclopropanesulfonamide.
4. A herbicidal composition comprising a composition according to any one of claims 1 to 3 and a pesticidally suitable adjuvant.
5. A method of controlling undesired plant growth comprising applying the herbicidal composition of any one of claims 1 to 4 to plants, the environment in which they grow or seeds thereof.
6. The use of the herbicidal composition as claimed in claims 1 to 4 for controlling weeds, wherein the weeds are one or more of grassy weeds and broadleaf weeds.
7. The use of the herbicidal composition according to claim 6, wherein the weeds are one or more of barnyard grass, moleplant seed, green bristlegrass, crabgrass, chickweed, wild oat, goosegrass, alopecuroide, and field thistle.
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