A binary herbicidal composition and use thereof

The use of binary herbicidal compositions solves the problems of weed resistance and herbicide tolerance, broadens the spectrum of weed control, reduces application rates, enhances weed control efficacy, and achieves an environmentally friendly weed control solution.

CN116849220BActive Publication Date: 2026-02-06QINGDAO KINGAGROOT CHEM COMPOUNDS CO LTD
View PDF 15 Cites 0 Cited by

Patent Information

Application Number
CN202310822346.9
Authority / Receiving Office
CN · China
Patent Type
Patents(China)
Current Assignee / Owner
Filing Date
2020-09-30
Publication Date
2026-02-06
Estimated Expiration
2040-09-30

AI Technical Summary

Technical Problem

Long-term use of single chemical herbicides has led to the evolution of herbicide resistance and tolerance in weeds, and existing herbicidal compositions are unable to effectively broaden the spectrum of weed control and reduce the amount of herbicide used.

Method used

A binary herbicidal composition is used, containing active ingredients A and B in a ratio of 1:100 to 2000:1, combined with conventional adjuvants such as carriers and surfactants, to prepare formulations such as dispersible oil suspensions, aqueous suspensions, suspension emulsions, wettable powders, emulsifiable concentrates, water-dispersible granules, water-in-oil emulsions, and microemulsions for the control of weeds.

Benefits of technology

It achieves a broadened spectrum of weed control, reduced application rate, enhanced weed control effect, solves the problem of resistant weeds, and is environmentally friendly, low-cost, and easy to use.

✦ Generated by Eureka AI based on patent content.

Smart Images

  • Figure CN116849220B_ABST
    Figure CN116849220B_ABST
Patent Text Reader

Abstract

The application belongs to the field of pesticides, and particularly relates to a binary herbicidal composition and application thereof. The binary herbicidal composition comprises a herbicidal effective amount of active ingredient A and active ingredient B, wherein the active ingredient A is cyprosulfuron, pyraclonil, benzofluor, trifloxysulfuron or the active ingredient B is selected from one of the following compounds and acids / salts / esters thereof: cinidon-ethyl, trifludimoxazin, indaziflam, tetflupyrolimet, dichloroisonixim, dimesulfazet, epyrifenacil and cyclopyrimorate. The composition can effectively prevent various weed problems, has the characteristics of expanding the herbicidal spectrum, reducing the application amount, being able to produce a synergistic effect and solving resistant weeds and the like.
Need to check novelty before this filing date? Find Prior Art

Description

[0001] This application is a divisional application of the Chinese Invention Patent Application with the application date of September 30, 2020, the application number of 202011061062.5, and the invention name of "a binary herbicidal composition and its application". TECHNICAL FIELD

[0002] The present application belongs to the field of pesticides, and specifically relates to a binary herbicidal composition and its application. BACKGROUND

[0003] Chemical weeding is the most economical and effective means in the prevention and control of weeds in farmland, but long-term continuous high-dose use of single variety or single action mode of chemical herbicides can easily cause weed resistance and resistance evolution and other problems. Rational compounding or mixing of herbicide compounds has the advantages of expanding the weed spectrum, improving the prevention and control effect, delaying the occurrence and development of weed resistance and drug resistance, etc., and is one of the most effective methods to solve the above problems. Therefore, it is urgent to develop a herbicidal composition variety with high safety, wide weed spectrum, synergistic effect and resistance to resistant weeds. SUMMARY

[0004] To solve the above problems in the prior art, the present application provides a binary herbicidal composition and its application. The composition can effectively prevent and control weeds such as Euphorbia humifusa, Galium aparine, Euphorbia humifusa, Euphorbia humifusa, Daucus carota, Euphorbia humifusa, and Euphorbia humifusa in crop fields, has the characteristics of expanding the weed spectrum, reducing the application amount, producing synergistic effect and solving the problem of resistant weeds.

[0005] A binary herbicidal composition comprises a herbicidal effective amount of active ingredient A and active ingredient B, wherein,

[0006] The active ingredient A is cyprosulfuron (CAS No. 1855929-45-1), metrafenone (CAS No. 1622908-18-2), benzofluor (CAS No. 1992017-55-6), and trifloxysulfuron (CAS No. 1911613-97-2),

[0007]

[0008] The active ingredient B is selected from one of the following compounds and its acid / salt / ester:

[0009] Cyclohexane (CAS No.: 87818-31-3), trifludimoxazin (CAS No.: 1258836-72-4), indazine-flufenoxam (CAS No.: 950782-86-2), tetflupyrolimet (CAS No.: 2053901-33-8), diclofenac-isoxazone (CAS No.: 81777-95-9), dimesulfazet (CAS No.: 1215111-77-5), epyrifenacil (CAS No.: 353292-31-6), cyclopyrimorate (CAS No.: 499231-24-2).

[0010] The weight ratio of A to B is 1:100 to 2000:1 or 1:90 to 1500:1; preferably 1:80 to 1000:1 or 1:70 to 800:1; more preferably 1:60 to 500:1 or 1:50 to 300:1; further preferably 1:40 to 200:1 or 1:30 to 100:1; even more preferably 1:20 to 80:1, 1:10 to 50:1, 1:5 to 30:1 or 1:1 to 10:1.

[0011] The mass percentage of A and B in the herbicidal composition is 1-95% of the total, preferably 10-80%.

[0012] The herbicidal composition also contains conventional adjuvants, including carriers and / or surfactants.

[0013] The term "carrier" in this article refers to an organic or inorganic, natural or synthetic substance. These facilitate the application of the active ingredient and are generally inert and must be agriculturally acceptable, particularly to the plant being treated. Carriers can be solid, such as clay, natural or synthetic silicates, silica, resins, waxes, solid fertilizers, etc.; or liquid, such as water, alcohols, ketones, petroleum fractions, aromatic or waxy hydrocarbons, chlorinated hydrocarbons, liquefied gas, etc.

[0014] The surfactants can include emulsifiers, dispersants or wetting agents, which can be ionic or non-ionic. Examples that can be mentioned are salts of polyacrylic acid, lignosulphonic acid, phenolsulphonic acid or naphthalenesulphonic acid, polymers of ethylene oxide with aliphatic or with aromatic alcohols or with aliphatic or with aromatic amines and with substituted phenols, in particular alkylphenols or arylphenols, salts of sulphosuccinic acid, taurine derivatives, in particular alkyl taurates, and phosphoric esters of alcohols or of polyhydroxyethoxylated phenols, alkylsulphonates, alkylarylsulphonates, alkyl sulphates, lauryl ether sulphates, fatty alcohol sulphates, and sulphated hexa-, hepta- and octadecanol, and sulphated fatty alcohol glycol ethers, furthermore condensates of naphthalene or of naphthalenesulphonic acid with phenol and formaldehyde, polyoxyethylene octylphenyl ether, ethoxylated isooctylphenol, octyl- or nonylphenol, alkylphenyl polyglycol ethers, tributylphenyl polyglycol ether, tristearylphenyl polyglycol ether, alkylaryl polyether alcohols, alcohol and fatty alcohol / ethylene oxide condensates, ethoxylated castor oil, polyoxyethylene alkyl ethers, ethoxylated polyoxypropylene, lauryl alcohol polyglycol ether acetal, sorbitol esters, lignosulphite waste liquors, and proteins, denatured proteins, polysaccharides, such as methylcellulose, hydrophobically modified starch, polyvinyl alcohol, polycarboxylates, polyalkoxylates, polyvinylamines, polyvinylpyrrolidone and copolymers thereof. At least one surfactant is required to be present in order to facilitate the dispersion of the active ingredients in water and to enable them to be applied correctly to the plants.

[0015] The compositions described above can also contain various other components, such as protective colloids, binders, thickeners, thixotropic agents, penetrants, stabilizers, sequestering agents, dyes, colorings and polymers.

[0016] In addition, the compositions of the present invention can be mixed with the following active substances, such as those in *World Encyclopedia of New Pesticide Varieties*, China Agricultural Science and Technology Press, September 2010, and known substances cited herein. Examples of herbicidal active substances mentioned below (Note: the name of the compound, either according to the common name of the International Organization for Standardization (ISO) or the chemical name, with a code where appropriate): acetochlor, butachlor, metolachlor, isopropachlor, isopropachlor, S-metolachlor, propachlor, chlorpyrifos, chlorpyrifos, chlorpyrifos, naphthalenepropionylchlor, R-L-naphthalenepropionylchlor, propargite, benzylthiamethoxam, bisbenzylchlor, pyrifluquinazon, chlorpyrifos, flubutyroxychlor, brobutyroxychlor, dimethoate, high-efficiency dimethoate, ethoxybenzylchlor, flumethiamethoxam, methoxythiamethoxam, pyrifluquinazon, isoxachlor, high-efficiency methyl parathion, high-efficiency methyl parathion, dipropionylchlor, clethodim, butyroxychlor Cyclopropamide, flusulfanilamide, heptamethrin, isobutanilamide, propyzamide, terbutanilamide, methylparaben, metolachlor, styraclostrobin, chlorpyrifos, acetochlor, valproic acid, pendimethalin, carbaryl, styraclostrobin, tricyclomethoate, butenazolamide, styraclostrobin, bensulfuron-methyl, naphthylpropamide, acetochlor, naphthylparaben, thiamethoxam, pyrimethanil, bensulfuron-methyl, chlorpyrifos, chlorpyrifos, butachlor, flupyrazole, atrazine, simazine, cypermethrin, cypermethrin, cypermethrin, pyrazosulfuron, chlorpyrifos ... Atrazine, cyprofen, cyprofen, cyprofen, cyprofen, methoxypropazine, cypermethrin, cyprofen, cyprofen, cyprofen, cyprofen, cyprofen, cyprofen, cyprofen, cyprofen, cyanuric acid, Indaziflam, chlorsulfuron, mesosulfuron, bensulfuron, chlorpyrifos, bensulfuron, thiasulfuron, pyrimisulfuron, mesosulfuron, sodium iodosulfuron, formamidosulfuron, ethersulfuron, etherbensulfuron, methylsulfuron, nicosulfuron, aminebensulfuron, acylsulfuron, ethoxysulfuron, cyprofensulfuron, sulfadiazine, sulfadiazine, tetrazoliumsulfuron, pyrimisulfuron, monosulfuron, monosulfuron, fluazolidone, flupyrimisulfuron, flupyrimisulfuron, cyclopyrimisulfuron, pyrimisulfuron, flupyrimisulfuron, flupyrimisulfuron, pyrimisulfuron, flupyrimisulfuron, pyrimisulfuron, flupyrimisulfuron, pyrimisulfuron, flupyrimisulfuron, pyrimisulfuron, pyrimisulfuron, trifluoromethyl Sulfuron, sulfonylsulfuron, trifluralin, flusulfanilamide, trifluralin, sodium sulfonylsulfuron, flupyrsulfuron, methoxysulfuron, pyrimethanil, propyrisulfuron, pyrimethanil, trifluralin, flusulfanilamide, quizalofop-p-ethyl, ethoxysulfuron, glyphosate, bensulfuron, chlorfluazuron, methylfluazuron, trifluralin, methoxysulfuron, trifluralin, flufenoxuron, flufenoxuron, chlorfluazuron, metolachlor, methylfluazuron, flufenoxuron, chlorfluazuron, methylfluazuron, methylfluazuron, halosafen, chlorfluazuron, isoproturon, linuron, diuron, sapura, fluroxypyr, bensulfuron, methylbensulfuron, bensulfuron, sulfothiamethoxamIsoxuron, terbutaline, clodinafop-methyl, chlorothalonil, methyl methazine, cyprodinil, methoxyfenozide, bromonazine, methoxyfenozide, chlorpyrifos, metribuzin, cyclorhizobium, fenitrothion, flusulfuron, glufosinate, fenprozil, isosulfuron, cyclorhizobium, thiamethoxam, thiamethoxam, fenprozil, thiamethoxam, thiamethoxam, thiamethoxam, thiamethoxam, oxazolium, Monisouron, Anisuron, Methiuron, Chloreturon, tetraflufenozide, betaine, betaine-ethyl, betaine, sulfadiazine, terbutaline, albendazole, fenprozil, chlorpyrifos, dichlorvos, metribuzin, chlorpyrifos, Carboxazole, Chlorprocarb, Fenasulam BCPC, CPPC, Carbasulam, Butadiene, Clethodim, Metrazine, Clethodim, Wild Grass, Permethrin, Clethodim, Barnyardgrass, Cypermethrin, Oat Grass, Dimethoate, Ethylmethoxam, Clethodim, Clethodim, Betaine, Cetylmethoxam, Thionylmethoxam, Methiobencarb, 2,4-D Isooctyl Butylester, 2,4-D Sodium Isooctyl Butylester, 2,4-D Isooctyl Butylester, 2,4-D Chloromethoxylate, 2,4-D Isooctyl Butylester ... Acetic acid, 2,4,5-t-propionic acid, 2,4,5-t-butyric acid, methyl 4-chloroamine salt, dicamba, sedge, valerate, cyhalofop-p-ethyl, trichlorobenzoic acid, aminodichlorobenzoic acid, methoxytrichlorobenzoic acid, quizalofop-p-ethyl, pyrfluthrin, quizalofop-p-ethyl, flupyrfluthrin, quizalofop-p-ethyl, quizalofop-p-ethyl, quizalofop-p-ethyl, oxazol, cyhalofop-p-ethyl, oxazolyl acetochlor, clodinafop, thiamethoxam, quizalofop-p-ethyl, haloxyfop-p-ethyl, trifluralin, isoxaflutole, paraquat, diquat, azoxystrobin, ethylbutyral, isopropaloxone, mesosulfuron-methyl, cyprofen, aminopropionol, ethylbutyral, chlorfluazol, diflubenzuron, chlorfluazol, mesopropalin, propionyl Nitrophenol, glyphosate, barnyardphos, glufosinate, methyl parathion, glyphosate, piperazine, diammonium phosphate, dimethoate, phosmet, fenpropathrin, fenpropathrin, fenpropathrin, dimethoate, fenpropathrin, imidacloprid, imidacloprid acetic acid, imidacloprid quinolinic acid, methoxymethylene, methoxymethylene ammonium salt, imidacloprid acetic acid, imidacloprid, clopyralid, clopyralid isooctyl ester, dichloropyridine acid, aminopyridine acid, trichloropyridine acid, fluthion, haloxypyridine, trichloropyridine phenol, thiamethoxam, flupyridine, clopyralid, flupyridine hydrazone, trichloropyridine butoxyethyl ester, cliodinate, clethodim, thiamethoxam, quizalofop-p-ethyl, cyclobenzanone, butenazol, oxadiazon, pyranazol, buthidazole, cyproconazole, cyclobenzanoneAmibuzin, acetamipridone, Ametridione, Amibuzin, bromobenzonitrile, octanoyl bromobenzonitrile, octanoyl iodobenzonitrile, iodobenzonitrile, diphenylacetonitrile, bispyribac-sodium, hydroxybispyribac-sodium, Iodobonil, pyrimethanil, diflubenzuron, penoxsulam, sulfadiazine, chlorpyrifos-sulfuron-methyl, dichlorvos-sulfuron-methyl, flumethrin, bispyribac-sodium, pyrimethanil, pyrimethanil, pyrimethanil, pyrimethanil, pyrimethanil, bispyribac-sulfuron-methyl, nicosulfuron-methyl, sulfadiazine, Tembotrione, Tefuryltrione, Bicyclopyrone, Ketodpiradox, isoxazin, isoxazin, Fenoxasulfone, Methi Ozolin, isopropalazine, pyrazosulfuron, pyrazosulfuron, pyrazosulfuron, bensulfuron, pyrazosulfuron, pyrazosulfuron, pyrazosulfuron, pyrazosulfuron, flumetsulam, pyrazosulfuron, pyrazosulfuron, pyrazosulfuron, flumethrin, mesotrione, pyrazosulfuron, flupropacil, pyrazosulfuron, pyrazosulfuron, pyrazosulfuron, pyrazosulfuron, flupropacil, pyrazosulfuron, flupropacil, pyrazosulfuron, flumetsulam, pentachlorophenol (sodium), terliphenol, terliphenol, terliphenol, pentonitrophenol, dinitrophenol, chlorpyrifos, terlisulfuron, terlisulfuron, terlisulfuron, terlisulfuron, terlisulfuron, terlisulfuron, terlisulfuron, terlisulfuron, terlisulfuron Herbicides such as chlorpyrifos, methyl methazine, tetrazolium chlorpyrifos, flupyridamole, chlorpyrifos, bromochlor, dimethoate, pyrazosulfuron, cyprodinil, pyrazosulfuron, pyrazosulfuron, cyprodinil, bentazon, pyrazosulfuron, oxadiazon, cyprodinil, isoxadiazon, cyclohexane, isopropyl methazine, propargite, indicarboxylate, sodium chlorate, cypermethrin, trichlorfon, etc. Chloroacetic acid, monochloroacetic acid, hexachloroacetone, tetrafluoropropionic acid, forage fastener, bromophenol oxime, triazole sulfonate, methomyl, furazolidone, furazolidone, ethoxysulfuron, pyrimethanil, chlorphthalic acid, flurfluthrin, barnyardgrass, acrolein, bensulfuron-methyl, metribuzin, oat ester, thiamethoxam, styracil, hydroxyzine, methoxybenzone, pyrimethanil, chlorpyrifos, trichloropropionic acid, Alorac, D Iethamquat, Etnipromid, Iprymidam, Ipfencarbazone, Thiencarbazone-methyl, Pyrimisulfan, Chlorflurazole, Tripropindan, Sulglycapin, methylsulfuron, Cambendichlor, Cyproterinic acid, Thiamethoxam, cypermethrin, cypermethrin, cypermethrin, cypermethrin, cypermethrin, cypermethrin, cypermethrin, pyrazole cypermethrin, furazolidone, oxadiazon, bis(oxazolyl)acrylic acid, dichloropropeneamine, fluorochloropyridinium ester, DOW fluorochloropyridinium ester, UBH-509, D489, LS 82-556KPP-300, NC-324, NC-330, KH-218, DPX-N8189, SC-0744, DOWCO 535, DK-8910, V-53482, PP-600, MBH-001, KIH-9201, ET-751, KIH-6127 and KIH-2023.

[0017] The herbicidal composition further comprises at least one safener selected from the group consisting of:

[0018] a) the class of the dichlorophenylpyrazoline-3-carboxylic acid (S1) compounds, preferred compounds are, for example, 1-(2,4-dichlorophenyl)-5-(ethoxycarbonyl)-5-methyl-2-pyrazoline-3- carboxylic acid ethyl ester (S1-1, mefenpyr-diethyl, PM, pages 594-595), and related compounds as described in, for example, WO 91 / 07874 and PM (pages 594-595).

[0019] b) the class of the dichlorophenylpyrazole carboxylic acid derivatives, preferred compounds are, for example, 1-(2,4-dichlorophenyl)-5-methylpyrazole-3-carboxylic acid ethyl ester (S1-2), 1-(2,4-dichlorophenyl)-5-isopropylpyrazole-3-carboxylic acid ethyl ester (S1-3), 1-(2,4-dichlorophenyl)-5-(1,1-dimethyl-ethyl)pyrazole-3-carboxylic acid ethyl ester (S1-4), 1-(2,4-dichlorophenyl)-5-phenylpyrazole-3-carboxylic acid ethyl ester (S1-5), and related compounds as described in EP-A-333131 and EP-A-269806.

[0020] c) the class of the triazole carboxylic acid (S1) compounds, preferred compounds are, for example, fenchlorazole, i.e. 1-(2,4-dichlorophenyl)-5-trichloromethyl-(1 H)-1,2,4-triazole-3-carboxylic acid ethyl ester (S1-6) and related compounds (see EP-A-174562 and EP-A-346620).

[0021] d) 5-benzyl- or 5-phenyl-2-isoxazoline-3-carboxylic acid or 5,5-diphenyl-2- isoxazoline-3-carboxylic acid compounds, preferred compounds are, for example, 5-(2,4- dichlorobenzyl)-2-isoxazoline-3-carboxylic acid ethyl ester (S1-7) or 5-phenyl-2- isoxazoline-3-carboxylic acid ethyl ester (S1-8) and related compounds described in WO 91 / 08202, or 5,5-diphenyl-2-isoxazoline-3-carboxylic acid ethyl ester (S1-9, isoxadifen- ethyl) or 5,5-diphenyl-2-isoxazoline-3-carboxylic acid n-propyl ester (S1-10) or 5-(4- fluorophenyl)-5-phenyl-2-isoxazoline-3-carboxylic acid ethyl ester (S1-11) described in patent application WO-A-95 / 07897.

[0022] e) 8-quinolinyloxyacetic acid (S2) compounds, preferably 1-methylhex-1-yl (5-chloro-8- quinolinyloxy) acetate (S2-1, cloquintocet-mexyl, as in PM (pages 195-196), (1,3- dimethylbut-1-yl)(5-chloro-8-quinolinyloxy) acetate (S2-2), 4-allyloxybutyl (5-chloro-8- quinolinyloxy) acetate (S2-3), 1-allyloxypropan-2-yl (5-chloro-8-quinolinyloxy) acetate (S2-4), (5-chloro-8-quinolinyloxy) ethyl acetate (S2-5), (5-chloro-8-quinolinyloxy) methyl acetate (S2-6), (5-chloro-8-quinolinyloxy) allyl acetate (S2-7), 2-(2- propyleneiminooxy)-1-ethyl (5-chloro-8-quinolinyloxy) acetate (S2-8), 2-oxopropan-1-yl (5-chloro-8-quinolinyloxy) acetate (S2-9), and related compounds described in EP-A-86750, EP-A-94349 and EP-A-191736 or EP-A-0492366.

[0023] f) (5-chloro-8-quinolinyloxy)malonic acid compounds, preferred compounds are, for example, (5-chloro-8-quinolinyloxy) malonic acid diethyl ester, (5-chloro-8-quinolinyloxy) malonic acid diallyl ester, (5-chloro-8-quinolinyloxy) malonic acid methyl ethyl ester and related compounds described in EP-A-0582198.

[0024] g) phenoxyacetic acid, phenoxypropionic acid or aromatic carboxylic acid active compounds, for example 2,4-dichlorophenoxyacetic acid (and esters) (2,4-D), 4-chloro-2- methylphenoxypropionic acid ester (mecoprop), MCPA or 3,6-dichloro-2-methoxybenzoic acid (and esters) (dicamba).

[0025] h) pyrimidines, for example "fenclorim" (PM, pages 386-387) (= 4,6-dichloro-2- phenylpyrimidine),

[0026] i) dichloroacetamides, which are used as pre-planting safeners (safeners for the soil), for example "dichloromid" (PM, pages 270-271) (= N,N-diallyl-2,2- dichloroacetamide), "AR-29148" (= 3-dichloroacetyl-2,2,5-trimethyl-1,3- oxazolidinone, available from Stauffer), "benoxacor" (PM, pages 74-75) (= 4- dichloroacetyl-3,4-dihydro-3-methyl-2H-1,4-benzoxazin), "APPG-1292" (= N- allyl-N-[(1,3-dioxolan-2-yl)-methyl]dichloroacetamide, available from PPG Industries), "ADK-24" (= N-allyl-N-[(allylaminocarbonyl)-methyl]-dichloroacetamide, available from Sagro-Chem), "AAD-67" or "AMON 4660" (= 3-dichloroacetyl-1 -oxa-3-aza- spiro[4,5]decane, available from Nitrokemia or Monsanto), "diclonon" or "ABAS 145138" or "ALAB 145138" (= (= 3-dichloroacetyl-2,5,5-trimethyl-1,3-diazabicyclo[4.3.0]nonane, available from BASF), and "furilazol" or "AMON 13900" (see PM, pages 482-483) (= (RS)-3-dichloroacetyl-5-(2-furanyl)-2,2-dimethyloxazolidinone),

[0027] j) dichloroacetone derivatives, for example "AMG 191 " (CAS Reg. No. 96420-72-3) (= 2-dichloromethyl-2-methyl-1,3-dioxolane, available from Nitrokemia),

[0028] k)Oxy-imino compounds are active compounds, known as seed dressing agents. Examples include "oxabetrinil" (PM, page 689) (=(Z)-1,3-dioxolane-2-ylmethoxyimino(phenyl)acetonitrile), which is used as a safer in seed dressing to prevent damage from metolachlor; and "fluxofenim" (PM, pages 467-468) (=1-(4-chlorophenyl)-2, 2,2-Trifluoro-1-acetone O-(1,3-dioxolane-2-ylmethyl)-oxime, which is used as a safer in seed dressing to prevent damage from metolachlor, and "cyometrinil" or "A-CGA-43089" (PM, page 983) (=(Z)-cyanomethoxyimino(phenyl)acetonitrile), which is also used as a safer in seed dressing to prevent damage from metolachlor.

[0029] 1) Thiazole carboxylic acid ester active compounds, known as seed dressing agents, such as "flurazol" (PM, pp. 450-451) (=2-chloro-4-trifluoromethyl-1,3-thiazol-5-carboxylic acid benzyl ester), which is used as a safener in seed dressing to prevent damage from alachlor and metolachlor.

[0030] m) Naphthalene dicarboxylic acid derivatives, which are active compounds known as seed dressing agents, such as "naphthalene dicarboxylic anhydride" (PM, pp. 1009-1010) (=1,8-naphthalene dicarboxylic anhydride), are used as safeners in corn seed dressing to prevent damage from thiocarbamate herbicides.

[0031] n) Active compounds derived from chromaneacetic acid, such as "ACL304415" (CAS Registry No. 31541-57-8) (=2-84-carboxychromane-4-yl)acetic acid, purchased from American Cynam.

[0032] o) Active compounds that, in addition to their herbicidal effect on harmful plants, also act as plant safety agents, such as "dimepiperate" or "AMY-93" (PM, pp. 302-303) (=S-1-methyl-1-phenylethylpiperidine-1-thiocarboxylate), "daimuron" or "ASK23" (PM, p. 247) (=1-(1-methyl-1-phenylethyl)-3-p-tolylurea), "benzuron" (c “umyluron” = “AJC-940” (=3-(2-chlorophenylmethyl)-1-(1-methyl-1-phenyl-ethyl)urea, see JP-A-60087254), “methoxyphenon” or “ANK049” (=3,3'-dimethyl-4-methoxy-benzophenone), “CSB” (=1-bromo-4-(chloromethylsulfonyl)benzene) (CAS Registry No. 54091-06-4, purchased from Kumiai).

[0033] The safener is preferably one or more of the following: bis(benzyloxazol) (CAS: 163520-33-0), cyprosulfamide (CAS: 221667-31-8), pyrazole-methyl (CAS: 135590-91-9), quinoline (CAS: 99607-70-2), gibberellic acid (CAS: 7-06-5), furilazole (CAS: 121776-33-8), and metcamifen (CAS: 129531-12-0).

[0034] In the context of this specification, if the abbreviation of the common name of the active compound is used, it includes, in each case, all conventional derivatives, such as esters and salts, and isomers, particularly optical isomers, especially one or more commercially available forms. If the common name indicates an ester or salt, it also includes, in each case, all other conventional derivatives, such as other esters and salts, free acids and neutral compounds, and isomers, particularly optical isomers, especially one or more commercially available forms. The chemical name of the compound given indicates at least one compound covered by the common name, which is generally preferred. In the case of sulfonamides such as sulfonylureas, the salt also includes salts formed by the exchange of hydrogen atoms in the sulfonamide group with a cation. For example, 2,4-chloro derivatives include, but are not limited to: sodium salt, potassium salt, dimethylammonium salt, isopropylamine salt, etc., as well as methyl 2,4-chloro, ethyl 2,4-chloro, isooctyl 2,4-chloro, ethyl 2,4-chloro, etc.; 2,4-D derivatives include, but are not limited to: 2,4-D salts such as sodium salt, potassium salt, dimethylammonium salt, triethanolamine salt, isopropylamine salt, choline, etc., as well as 2,4-D esters such as methyl 2,4-chloro, ethyl 2,4-chloro, butyl 2,4-chloro, isooctyl 2,4-chloro, etc.

[0035] The composition of the present application can be used directly or diluted by the user before use. It can be prepared by the usual processing methods, i.e. by mixing the active substance with liquid solvents or solid carriers and, if desired, one or more surfactants such as dispersants, stabilizers, wetting agents, tackifiers, defoamers and the like.

[0036] Specific formulations of the herbicidal composition are dispersible oil concentrates, aqueous suspensions, suspoemulsions, wettable powders, emulsifiable concentrates, water-dispersible granules (dry flowables), emulsions, microemulsions.

[0037] In short, the composition of the present application can be mixed with solid and liquid additives conventionally used in the formulations of the prior art. The amount of active ingredient used varies with the external conditions, such as temperature, humidity, nature of the herbicide used, etc. It can vary greatly, for example between 0.001 and 1.0 kg / ha, or more of active substance, but preferably between 0.005 and 750 g / ha, in particular between 0.005 and 500 g / ha.

[0038] In addition, the composition of the present application can be applied to the leaves of the plants to be treated, i.e. to the weeds, in particular to the surface affected by the weed infestation or susceptible to infestation, by the method of spraying.

[0039] Further, the present application also provides the use of the herbicidal composition in controlling weeds; and a method for controlling the growth of unwanted plants, which comprises applying the herbicidal composition to the plants, plant parts, plant seeds or areas where the plants grow. Preferably, the herbicidal composition is used for selectively controlling weeds in useful crops, more preferably the useful crops are genetically modified crops or crops treated by genome editing technology.

[0040] The compounds of the present application can be used for the treatment of all plants and plant parts. The plants varieties and cultivars can be obtained by traditional breeding methods or by biotechnological methods or by combinations of both. Genetically modified plants (GM

[0041] Genetically modified plant cultivars that can be treated according to the application include those that are resistant to one or more biotic stresses (pests, such as nematode animals, insects, mites, fungi, etc.) or abiotic stresses (drought, cold, soil

[0042] When the herbicidal compositions of the present application are applied, unexpected synergistic effects are obtained and the herbicidal activity is more pronounced than the expected sum of the activities of the individual herbicides used, as well as more pronounced than the activity of the individual herbicides. The synergistic effects are manifested in reduced application rates, a broader spectrum of weed control, faster and more persistent herbicidal action, properties that are desirable in weed control practice. In terms of the properties described, the new compositions are clearly superior to existing herbicides, allowing for reduced use, and are more environmentally friendly.

[0043] The synergistic herbicidal compositions of the present application also have the following advantages:

[0044] (1) The compositions of the present application are environmentally friendly and are readily degradable in the environment.

[0045] (2) The herbicidal compositions of the present application are low cost, easy to use, and have great economic and social benefits in terms of their widespread application. DETAILED DESCRIPTION

[0046] The following examples are not intended to limit the present application, but merely serve to illustrate how the present application can be implemented. For certain weeds, these examples show particularly significant effectiveness. Examples are as follows:

[0047] Phytotoxicity test:

[0048] 1) Test target:

[0049] Mai Jiagong, Oxalis corniculata, Euphorbia humifusa, Lycianthes integrifolia, Daucus carota, Coronopus didymus, Cannabis sativa.

[0050] 2) Reagents:

[0051] The active ingredients A required, amicarbazone, pyroxasulfone, benzofluor, trifloxysulfuron, are produced by the company, and others are purchased from reagent companies. The technical agents are all diluted with acetone as solvent, and 0.1% emulsifier Tween-80 aqueous solution is used for dilution.

[0052] Among them, From patent CN202010281666.4, the preparation method is as follows:

[0053] (1) a (20 g, 98.3 mmol, 1.0 eq) was added in 200 ml of EtOH, then the reaction solution was added dropwise NH2OH HCl (7.5 g, 108.1 mmol, 1.1 eq) aqueous solution (30 ml) at 0 ℃. After the dropwise addition was completed, the reaction solution was stirred at 0 ℃ for 3 hours, LCMS detection showed that the raw material was almost consumed, and a main new peak was generated. After the reaction solution was concentrated to remove part of the ethanol, it was poured into 100 ml of water, a solid was precipitated, filtered, the filter cake was washed with water and dried to obtain b (20 g, 93% yield) (white solid).

[0054]

[0055] (2) b (5 g, 22.9 mmol, 1.0 eq), Fe powder (3.8 g, 68.6 mmol, 3 eq), NH4Cl (2.5 g, 45.8 mmol, 2 eq) and water (10 ml) were added in 50 ml of EtOH. Then the reaction solution was reacted at 80 ℃ for 1 hour, and LCMS detection showed that the product peak was detected. The reaction solution was filtered with diatomite, concentrated to remove ethanol, and then water (20 ml) was added, extracted with ethyl acetate, and concentrated to obtain black crude product. After the crude product was separated and purified by column chromatography, c (2 g, 46.4% yield) (gray solid) was obtained.

[0056]

[0057] (3) c (1 g, 5.3 mmol, 1.0 eq) and d (1.1 g, 5.3 mmol, 1.0 eq) were added in 20 ml of acetic acid, and the reaction solution was reacted at 110 ℃ for 1 hour. LCMS detection showed that the raw material was basically reacted, and the main peak was the product. After the solvent was concentrated, the crude product was separated by column chromatography to obtain e (1.5 g, 80.5% yield) (white solid).

[0058]

[0059] (4) e (0.4 g, 1.1 mmol, 1.5 eq), f (0.18 g, 1.5 mmol, 1.3 eq) and K2CO3 (0.2 g, 1.5 mmol, 1.3 eq) were added in 8 ml of DMF, and then the reaction solution was reacted at 25 ℃ for 4 hours, LCMS detection showed that the product was obtained. After water (10 ml) was added to the reaction solution, it was extracted with ethyl acetate, the organic phase was washed with saturated brine (10 ml*1), and the organic phase was concentrated, and the crude product was separated by column chromatography to obtain g (0.3 g, 60.2% yield) (white solid).

[0060]

[0061] (5) In 6 ml DMF, g (0.3 g, 0.69 mmol, 1.0 eq), Mel (0.13 g, 0.9 mmol, 1.3 eq) and K2CO3 (0.12 g, 0.9 mmol, 1.3 eq) were added successively, and then the reaction solution was reacted at 25°C for 2 hours. LCMS detected the product. After adding water (10 ml) to the reaction solution, it was extracted with ethyl acetate, and the organic phase was washed with saturated brine (10 ml*1). After concentrating the organic phase, the crude product was separated by column chromatography to obtain the target product (0.2 g, 64.6% yield, R / S = 99 / 1) (white solid).

[0062]

[0063] 1 H NMR (500 MHz, DMSO) δ 8.52 (s, 1H), 7.93 (d, J = 7.5 Hz, 1H), 7.88 (d, J = 9.5 Hz, 1H), 6.61 (s, 1H), 4.89-4.87 (m, 1H), 3.70 (s, 3H), 3.43 (s, 3H), 1.48 (d, J = 7.0 Hz, 3H).

[0064] 3), Test method

[0065] 3.1), Post-emergence stem and leaf spray treatment:

[0066] The weeds were cultivated by potting method, and when the weeds were at the 3-4 leaf stage, stem and leaf spraying was uniformly sprayed, and the spraying amount was 450 kg / ha.

[0067] 3.2), Soil sealing treatment:

[0068] The pot was sown and covered with soil, and the soil surface was uniformly sprayed before the weeds germinated, and the spraying amount was 450 kg / ha.

[0069] 4), Data investigation and statistical analysis

[0070] 4.1), Investigation method

[0071] The absolute number investigation method was used, the survival weeds were cut off whole seedlings along the soil surface with a blade, and the fresh weight of the weeds was weighed with an analytical balance. For the dead weeds, the fresh weight was zero.

[0072] 4.2), Investigation time and frequency

[0073] After treatment, it was moved into the greenhouse for conventional culture for 21 days, and a total of 1 time was investigated.

[0074] 4.3), data statistical analysis

[0075] The theoretical fresh weight inhibition rate (E0=X+Y-X*Y / 100) of each treatment combination was calculated by Gowing method, and then compared with the measured inhibition rate (E) to evaluate the joint action type of the two mixtures on weeds. When the value of E-E0 is greater than 10%, it is synergistic effect; when it is less than -10%, it is antagonistic effect; when it is between -10% and 10%, it is additive effect. The best ratio is determined according to the actual control effect, the characteristics of herbicides, the balance of formula and other factors. In the formula, X is the fresh weight inhibition rate when the amount of active ingredient A is P; Y is the fresh weight inhibition rate when the amount of active ingredient B is Q.

[0076] The statistical results are shown in Tables 1-34 below. Except for the post-emergence stem and leaf spraying treatment, the others are soil closed treatment.

[0077] Table 1 Actual control effect and joint action evaluation of mixtures of cyclopyrimorate and indaziflam on Eupatorium odoratum

[0078]

[0079] Table 2 Actual control effect and joint action evaluation of mixtures of cyclopyrimorate and tetflupyrolimet on Eupatorium odoratum

[0080]

[0081] Table 3 Actual control effect and joint action evaluation of mixtures of cyclopyrimorate and dimesulfazet on Eupatorium odoratum

[0082]

[0083] Table 4 Actual control effect and joint action evaluation of mixtures of cyclopyrimorate and epyrifenacil on Eupatorium odoratum (post-emergence stem and leaf spraying treatment)

[0084]

[0085] Table 5 Actual control effect and joint action evaluation of mixtures of pyraclonil and indaziflam on Portulaca oleracea

[0086]

[0087] Table 6 Actual control effect and joint action evaluation of mixtures of pyraclonil and tetflupyrolimet on Portulaca oleracea

[0088]

[0089]

[0090] Table 7 Actual control effect and joint action evaluation of bensulfuron-methyl + pyroxasulfone on broadleaf weeds in corn

[0091]

[0092] Table 8 Actual control effect and joint action evaluation of bensulfuron-methyl + epyrifenacil on broadleaf weeds in corn (post-emergence stem-leaf spray treatment)

[0093]

[0094] Table 9 Actual control effect and joint action evaluation of benzobicyclon + indaziflam on broadleaf weeds in corn

[0095]

[0096] Table 10 Actual control effect and joint action evaluation of benzobicyclon + tetflupyrolimet on broadleaf weeds in corn

[0097]

[0098] Table 11 Actual control effect and joint action evaluation of benzobicyclon + dimesulfazet on broadleaf weeds in corn

[0099]

[0100] Table 12 Actual control effect and joint action evaluation of benzobicyclon + epyrifenacil on broadleaf weeds in corn (post-emergence stem-leaf spray treatment)

[0101]

[0102]

[0103] Table 13 Actual control effect and joint action evaluation of metribuzin + indaziflam on broadleaf weeds in corn

[0104]

[0105] Table 14 Actual control effect and joint action evaluation of metribuzin + tetflupyrolimet on broadleaf weeds in corn

[0106]

[0107] Table 15 Actual control effect and joint action evaluation of metribuzin + dimesulfazet on broadleaf weeds in corn

[0108]

[0109] Table 16 Actual control effect and joint action evaluation of mixtures of triazifentyl with epyrifenacil on rice (post-emergence stem-leaf spray treatment)

[0110]

[0111] Table 17 Actual control effect and joint action evaluation of mixtures of trifludimoxazin on daucus carota

[0112]

[0113] Table 18 Actual control effect and joint action evaluation of mixtures of indaziflam on daucus carota

[0114]

[0115]

[0116] Table 19 Actual control effect and joint action evaluation of mixtures of tetflupyrolimet on daucus carota

[0117]

[0118] Table 20 Actual control effect and joint action evaluation of mixtures of dimesulfazet on daucus carota

[0119]

[0120] Table 21 Actual control effect and joint action evaluation of mixtures of epyrifenacil on daucus carota (post-emergence stem-leaf spray treatment)

[0121]

[0122] Table 22 Actual control effect and joint action evaluation of mixtures of cyclopyrimorate on daucus carota

[0123]

[0124] Table 23 Actual control effect and joint action evaluation of mixtures of cinmethylin on coriandrum sativum

[0125]

[0126]

[0127] Table 24 Actual control efficacy and joint action evaluation of mixed trifludimoxazin on coriander

[0128]

[0129] Table 25 Actual control efficacy and joint action evaluation of mixed indaziflam on coriander

[0130]

[0131] Table 26 Actual control efficacy and joint action evaluation of mixed tetflupyrolimet on coriander

[0132]

[0133] Table 27 Actual control efficacy and joint action evaluation of mixed dichloroisoniximofen on coriander

[0134]

[0135] Table 28 Actual control efficacy and joint action evaluation of mixed dimesulfazet on coriander

[0136]

[0137] Table 29 Actual control efficacy and joint action evaluation of mixed epyrifenacil on coriander

[0138]

[0139] Table 30 Actual control efficacy and joint action evaluation of mixed cyclopyrimorate on coriander

[0140]

[0141] Table 31 Actual control efficacy and joint action evaluation of mixed tetflupyrolimet on spilanthes

[0142]

[0143] Table 32 Actual control efficacy and joint action evaluation of mixed dimesulfazet on spilanthes

[0144]

[0145] Table 33 Actual control effect of mixed cypromid on purslane and joint action evaluation

[0146]

[0147] Table 34 Actual control effect of mixed cyclopyrimorate on purslane and joint action evaluation

[0148]

[0149] Through a large number of experiments and exploration, the present application unexpectedly found that the composition is used for preventing and removing Gramineae, sedge family, broad-leaved weeds such as Echinochloa crus-galli, Brassica hirta, Euphorbia humifusa, Smilax china, Daucus carota, Coronopus didymus, Portulaca oleracea, etc., has a surprising and unexpected synergistic effect, which is more significant at a low dosage, can reduce the amount of drug, reduce environmental pollution, and reasonable compounding reduces the cost of agricultural use, is efficient for ALS and ACCase inhibitor-resistant weeds, has a good application prospect. At the same time, through testing in wheat fields, corn fields, rice fields, peanuts, sugarcane, sorghum, millet, potatoes, rapeseed, soybeans, cotton, vegetables, bluegrass, tall fescue, St. Augustine grass, etc., it shows good selectivity and excellent synergistic effect, and can be developed into a herbicide mixture with wide market value.

Claims

1. A binary herbicidal composition characterized in that, comprising a herbicidally effective amount of active ingredient A and active ingredient B, wherein Active ingredient A is cyprosulfamide, dicyclanil, fluridone, flurochloridone, mesotrione, norflurazon, pyridate, or active ingredient B is tetflupyrolimet; When A is the weight ratio of A, B in the herbicidal composition is 225:112-450:14; when A is benzobicyclon, the weight ratio of A:B in the herbicidal composition is 1:5-1:

1. when A is benzobicyclon, the weight ratio of A:B in the herbicidal composition is 1:5-1:

1. when A is benzobicyclon, the weight ratio of A:B in the herbicidal composition is 1:5-1:

1. When A is the weight ratio of A, B in the herbicidal composition is 187.5:112.5-375:

14.

2. A binary herbicidal composition characterized in that, comprising a herbicidally effective amount of active ingredient A and active ingredient B, wherein Active ingredient A is cyprosulfamide, dicyclanil, fluridone, flurochloridone, mesotrione, norflurazon, pyridate, or active ingredient B is tetflupyrolimet; When A is the weight ratio of A, B in the herbicidal composition is 1:1-30:1; when A is benzobicyclon, the weight ratio of A:B in the herbicidal composition is 1:5-1:

1. when A is benzobicyclon, the weight ratio of A:B in the herbicidal composition is 1:5-1:

1.

3. The binary herbicidal composition according to claim 2, wherein When A is the weight ratio of A, B in the herbicidal composition is 1:1-10:1; when A is benzobicyclon, the weight ratio of A:B in the herbicidal composition is 1:5-1:

1.

4. A binary herbicidal composition according to any one of claims 1 to 3, wherein the herbicidal composition comprises the compound of formula (I) and the compound of formula (II). the mass percentage of A:B in the herbicidal composition is 1-95% of the total amount.

5. A binary herbicidal composition according to claim 4, wherein the mass percentage of A:B in the herbicidal composition is 10-80% of the total amount.

6. A binary herbicidal composition according to any one of claims 1 to 3, wherein the herbicidal composition comprises a compound of formula (I) and a compound of formula (II). the herbicidal composition further comprises conventional adjuvants.

7. A binary herbicidal composition according to claim 6, wherein the conventional adjuvants comprise carriers and / or surfactants.

8. A binary herbicidal composition according to any one of claims 1 to 3, wherein the herbicidal composition comprises a compound of formula (I) and a compound of formula (II). the herbicidal composition further comprises at least one safener.

9. A binary herbicidal composition according to claim 8, wherein the safener is selected from one or more of isoxadifen-ethyl, cyprosulfamide, metcamifen, furilazole, and azafenidin.

10. A binary herbicidal composition according to any one of claims 1 to 3, wherein the herbicidal composition comprises a compound of formula (I) and a compound of formula (II). the specific formulation of the herbicidal composition is dispersible oil suspension, aqueous suspension, suspoemulsion, wettable powder, emulsifiable concentrate, water dispersible granule, emulsion in water, or microemulsion.

11. Use of a binary herbicidal composition according to any one of claims 1 to 10 for controlling weeds, characterized in that the herbicidal composition is used for selectively controlling weeds in useful crops.

12. Use of a binary herbicidal composition according to claim 11 for controlling weeds, characterized in that the useful crops are genetically modified crops or crops treated by genome editing technology.

13. A method for controlling unwanted plant growth, comprising applying the binary herbicidal composition according to any one of claims 1-10 to plants, plant parts, plant seeds, or areas where plants grow.

14. A method of controlling undesirable plant growth according to claim 13, wherein, the herbicidal composition is used for selectively controlling weeds in useful crops.

15. A method of controlling undesirable plant growth according to claim 14, wherein, the useful crops are genetically modified crops or crops treated by genome editing technology.

Citation Information

Patent Citations

  • Herbicidal triazoles

    CN106659159A

  • Use of quinoline derivatives in the protection of crop plants

    EP0086750A2

  • Use of quinoline derivatives for the protection of cultivated plants

    EP0094349A2

  • Plant protecting agents based on 1,2,4 - triazole derivatives as well as 1,2,4-triazole derivatives

    EP0174562A2

  • Use of quinoline derivatives for the protection of crop plants

    EP0191736A2