CN117941694A - Herbicidal compositions comprising substituted pyrimidine formyl oximes and use thereof - Google Patents

Abstract

The invention belongs to the field of pesticides, and particularly relates to a weeding composition containing substituted pyrimidine formyl oxime compounds and application thereof. The composition comprises an active ingredient A and an active ingredient B in herbicidally effective amounts, wherein the active ingredient A is

Description

Herbicidal compositions comprising substituted pyrimidine formyl oximes and use thereof

Technical Field

The invention belongs to the field of pesticides, and particularly relates to a weeding composition containing substituted pyrimidine formyl oxime compounds and application thereof.

Background

Chemical weeding is the most economical and effective means in farmland weed control, but long-term continuous high-dosage chemical herbicide with single variety or single action mode is easy to cause problems of weed resistance, resistance evolution and the like. The reasonable compounding or compounding of the herbicide compound has the advantages of expanding the weed spectrum, improving the preventing and killing effect, delaying the occurrence and development of weed resistance and drug resistance, and the like, is one of the most effective methods for solving the problems, and still needs to develop a herbicide composition variety with high safety, broad herbicide spectrum, capability of generating synergistic effect and solving the problem of resistant weeds in production.

Disclosure of Invention

In order to solve the problems in the prior art, the invention provides a weeding composition containing substituted pyrimidine formyl oxime compounds and application thereof. The composition can effectively prevent and remove broadleaf weeds or grassy weeds, and has the characteristics of expanding weed control spectrum, reducing application amount, generating synergistic effect, solving resistant weeds, and the like.

A herbicidal composition comprising a substituted pyrimidine formyl oxime compound and its use, comprising a herbicidally effective amount of active ingredient A and active ingredient B, wherein,

The active component A is

The active ingredient B is selected from one or more of the following compounds: amicarbazone (CAS: 1992017-55-6), mesotrione (CAS: 104206-82-8), topramezone (CAS: 210631-68-8), isoxaflutole (CAS: 141112-29-0), fluoxastrobin (CAS: 352010-68-5), tolpyralate (CAS: 1101132-67-5), nicosulfuron (CAS: 111991-09-4), foramsulfuron (CAS: 173159-57-4), atrazine (CAS: 1912-24-9), terbuthylazine (CAS: 5915-41-3).

Wherein, the weight ratio of A, B in the weeding composition is 1:300-50:1, 1:250-20:1, 1:200-10:1, 1:160-5:1, 1:100-3:1, 1:60-1:1, 1:50-1:3, 1:30-1:5 or 1:20-1:10.

In a specific embodiment, the herbicidal composition is selected from any one of the following:

The active component A is The active ingredient B is selected from one or more of the following compounds: the weight ratio of A, B in the weeding composition is 1:30-1:1, preferably 1:20-4:5;

The active component A is The active ingredient B is topramezone, and the weight ratio of A, B in the weeding composition is 1:10-5:1, preferably 1:6-8:3;

The active component A is The active component B is Tolpyralate, and the weight ratio of A, B in the weeding composition is 1:70-1:1, preferably 1:50-8:25;

The active component A is The active ingredient B is selected from one or more of the following compounds: the weight ratio of A, B in the weeding composition is 1:20-5:1, preferably 1:10-2:1;

The active component A is The active ingredient B is selected from one or more of the following compounds: the weight ratio of A, B in the weeding composition is 1:250-1:5, preferably 1:200-1:10.

The mass percentage of A and B in the weeding composition accounts for 1-95% of the total amount, and preferably 1-80%.

The herbicidal composition further comprises conventional adjuvants including carriers and/or surfactants.

The term "carrier" as used herein means an organic or inorganic, natural or synthetic substance. They facilitate the application of the active ingredient, which carriers are generally inert and must be agriculturally acceptable, in particular by the treated plants. The carrier may be solid, such as clay, natural or synthetic silicate, silica, resin, wax, solid fertilizer, etc.; or liquid, such as water, alcohols, ketones, petroleum fractions, aromatic or waxy hydrocarbons, chlorinated hydrocarbons, liquefied gases, and the like.

Surfactants may include emulsifiers, dispersants or wetting agents, which may be ionic or nonionic. Examples which may be mentioned are salts of polyacrylic acid, lignosulfonates, salts of phenolsulfonic acid or naphthalenesulfonic acid, polymers of ethylene oxide with aliphatic alcohols or with aliphatic amines with substituted phenols, in particular alkylphenols or arylphenols, sulfosuccinates, taurine derivatives, in particular taurates, and phosphates of alcohols or of polyethylated phenols, alkylsulfonates, alkylaryl sulfonates, alkyl sulfates, lauryl ether sulfates, fatty alcohol sulfates, and also sulfated hexadecyl-, heptadeca-and octadecanols and sulfated fatty alcohol glycol ethers, furthermore condensates of naphthalene or naphthalenesulfonic acid with phenol and formaldehyde, polyoxyethylene octylphenyl ether, ethoxylated isooctylphenols, octylphenols or nonylphenols, alkylphenyl polyglycol ethers, tributylphenyl polyglycol ethers, tristearylphenyl polyglycol ethers, alkylaryl polyether alcohols, alcohol and fatty alcohol/ethylene oxide condensates, ethoxylated castor oil, polyoxyethylene alkyl ethers, ethoxylated polyoxypropylene, lauryl alcohol polyglycol ethers, sorbitol esters, lignin sulfite waste solutions, and also proteins, polysaccharides (e.g. methylcellulose), polyvinyl alcohol, hydrophobically modified polyvinyl pyrrolidone, polyvinyl alcohol carboxylate, polyvinyl pyrrolidone, and copolymers thereof. At least one surfactant is required to be present to facilitate the dispersion of the active ingredients in water and to enable them to be applied correctly to the plants.

The above-described compositions may also contain various other components such as protective colloids, binders, thickeners, thixotropic agents, penetrating agents, stabilizers, chelating agents, dyes, colorants and polymers.

In addition, the compositions of the present invention may be mixed with active substances such as known substances from the world technical university of new agricultural chemicals, chinese agricultural science and technology press 2010.9 and the literature cited therein. For example the herbicide active substances mentioned below, (remarks: the name of the compound, either a common name according to the international organization for standardization (ISO), or a chemical name, where appropriate with a code): acetochlor, butachlor, alachlor, metolachlor, mefenacet, pretilachlor, kefenacet, naproxen, R-valicarb-isopropyl, propanil, mefenacet, diflufenican, oxadiazon, fluofen, butachlor, bromobutachlor, dimethenamid, high-efficiency dimethenamid, ethofenuron, flufenacet, methoxam, metazachlor, high-efficiency mevalicarb-isopropyl, alachlor, dimethenamid, sulfenamide, heptanamide, ibut-sodium, propisochlor, terbutamide, dimethenamid, metolachlor, tricyclam the composition comprises chlormequat, propyzamide, valicarb, carpronium, neo-Yan, tricyclocet-oxamine, butachlor, gramine, benoxamide, quinone-azolium, benfomesamine, naproxen, acetochlor, naproxen, thiabendazole, pyrifos, benoxaden, oxaden, chlorphthalimide, dingan, fluopicolide, atrazine, simazine, prometryn, cyanogen, simetryn, amethoxine, prometryn, fluoxyzine, terbutryn, triazoxamine, ciprofloxane, prometryn, bentazone, prometryn, simetryn, triamcinolone, terbutryn, clomazone, chlorprometryn, cola, prometryn, fluazuron, fluben, atractyl, bentazone, liquorice, cyanuric acid, indaziflam, chlorsulfuron, metsulfuron, bensulfuron methyl, chlorimuron ethyl, tribenuron methyl, thisulfuron methyl, pyrazosulfuron ethyl, methyl disulfuron methyl, methyl iodisulfuron sodium salt, formamidosulfuron, cinosulfuron, metsulfuron, nicosulfuron, amisulfuron, amidosulfuron, ethoxysulfuron, cyclosulfamuron, rimsulfuron, tetrazole sulfuron, flazasulfuron monosulfuron, flucarbazone, fluflazasulfuron, flupyrazosulfuron, halosulfuron-methyl, fluazimsulfuron, propylbenzene sulfonic acid, trifloxysulfuron, sulfosulfuron, trifloxysulfuron, fluazinam Fluosulfuron, triflusulfuron-methyl, mesosulfuron sodium, flupyrsulfuron-methyl, mesosulfuron-methyl, azosulfuron-ethyl, propyrisulfuron (propyrisulfuron), oxaziclomefone, acifluorfen, fomesafen lactofen, fluoroglycofen-ethyl, oxyfluorfen, cumyl ether, benomyl, clofluroxypyr-meptyl, carbobenzoxim, trifluoperal, methoxyfenoxyfen, trinitrofen, fluoroglycofen, fluroxypyr-meptyl, herbicidal ethers, pyriftalid, trifluoperal, halosafen, chlortoluron, isoproturon, diuron, sepouron, trifluouron, thifenuron, metsulfuron-methyl, thifluzaron bensulfuron methyl, thiosulfuron, clomazone, tebuthiuron, clodinafop-propargyl, tribenuron-methyl, mesotrione, methosulfuron, bromuron, methosulfuron, chlorsulfuron, cycloxysulfuron, chlorsulfuron non-chlorazuron, flucarbazone, diuron, cumarone, diuron, isodiuron, cyclouron, thifluuron, buthiuron, diuron, p-fluron, methamidothiazuron, long Caote, tri-isourea, oxazouron, monisouron, anisuron, methiuron, chloreturon, trifluouron, phenytoin-ethyl, betametham, sulbenazolin, terbutryn, avenanthramide, dazomet, chloranil, diclofenac, clomazone, clodinafop-propargyl, carboxazole, chlorprocarb, fenasulam, BCPC, CPPC, carbasulam, butachlor, graminium, imago, graminium, imazamox, pethaline, cycloxaprine, avenanthramide, midothiox, captan, kefierce, prosulfan, secondary sudan, thiomethoprene, benazolan, clomazone, isopolinate, methiobencarb, 2,4-D isooctyl butyl, 2-methyl 4-sodium chloride, 2,4-D isooctyl sodium salt, 2,4-D isooctyl dimethylamine salt, 2-methyl 4-ethyl thiodicate, 2,4-D isooctyl propionic acid, high 2,4-D isooctyl salt, 2,4-D isooctyl butyric acid, 2, 4-chloro propionic acid, 2-chloro butyric acid, 4-methyl butyric acid, 4-chloro propionic acid; 2,4, 5-nasal discharge, 2,4, 5-nasal discharge propionic acid, 2,4, 5-nasal discharge butyric acid, 2-methyl 4-chloroamine salt, dicamba, imazalil, valicarb, triamcinolone, amisulbrom, mebendazole, haloxyfop, fluazifop-p-butyl, haloxyfop-methyl, quizalofop-p-ethyl, quizalofop-ethyl, oxazalofop-ethyl, fenoxaprop-p-ethyl, oxazalofop-ethyl, cyhalofop-butyl, oxazalofop-ethyl, oxazalofop-butyl, cyhalofop-butyl, oxazalofop-butyl, trifluor-methyl, trifluralin, 34, propiophenol, prochlorazol, glyphosate, anilofos, glufosinate, methamidophos, glufosinate, pirfosinate, bialaphos, triazophos, imazapyr, praziquantel, vinphos, validronate, dimefon, imazethapyr imidazoquinolinic acid, imazethapyr ammonium salt, imazethapyr, imazamox, fluroxypyr, isooctyl fluroxypyr, clopyralid, picloram, triclopyr Fluosulfan, haloxydine, triclopyr, thiotepa, fluazinone, aminopyralid, diflufenzopyr, butoxyethyl triclopyr, cliodinate, sethoxydim, clethodim, thioxanthone, graminetin, cycloxapride, fenbufen, oxime, pyrone, buthidazole, oxazin, cycloxazinone, oxazinone, buprofezin, ametridione, amibuzin, bromoxynil octanoate, xin Xiandian benzonitrile, iodoxynil Dithalonitrile, diphenylacetonitrile, biscarfentrazone-ethyl, hydroxydichlorvos, iodobonil, flumetsulam, florasulam, penoxsulam, sulfentrazone-ethyl, clomazone, diclosulam, pyroxsulam, fluor-methyl, bispyribac-sodium, pyribenzoxim, pyriftalid, pyriminobac-methyl, bicyclosulzin, mesotrione, sulfentrazone, tembotrione, tefuryltrione, bicyclopyrone, ketodpiradox, isoxaflutole, clomazone, fenoxasulfone, methiozolin, propisochlor pyraflufen-ethyl, pyrazolote, delphinidin, benoxazal, pirflux, metachlor, pyrasulfotole, topramezone, pyroxasulfone, flumetsulam, carfentrazone-ethyl, amicarbazone, carfentrazone-ethyl, flumetsulam, sulfentrazone-ethyl, bencarbazone, benoxadone, flumetsulam, triclopyr, clomazone, terfenazal, flupropacil, indolone, flumetsulam, clodinafop-propargyl, phtalol, flumezin, pentachlorophenol (sodium), dinol, terfenacil, ter Le Zhi, pentanitrophenol, dinitrophenol, chloronitrophenol, dilarol, propyzamide, oxadiazon, cyclopentaoxadiazon, flumetsulam, methyl zinate, tebuconazole, fluidazinate, chlorphenamine, chlorpyrim, dimethachlor, pyrideth, pyridazone, bentazone, pyridate, pyridafol, quinclorac, clomefone, bentazone, pyridate, oxazinone, benazolone, isoprothiolane, clomazone, cycloheptanether, isopropyl ether, propyl ether, indenone, sodium chlorate, coumarone, trichloroacetic acid, monochloroacetic acid, hexachloroacetone, tetrafluoropropionic acid, pasture, paraquat, fluazifom, chlorpyrifos bromphenol oxime, triazolesulfone, mefenacet, furbenone, furbenfursul, furbenoxaden, clomazone, chlorphthalic acid, fludioxonil, barnyard grass, acrolein, benoxaden, mefenacet, oat ester, tiazoxamide, gossypine, oxycodone, metrafenone, saflufenacil, chlor, triclopyr 、Alorac、Diethamquat、Etnipromid、Iprymidam、Ipfencarbazone、Thiencarbazone-methyl、Pyrimisulfan、Chlorflurazole、Tripropindan、Sulglycapin、 mebendazole Cambendichlor, ciprofloxacin, thiocyanidine, clomazone, benoxacor, benoxaquin, benoxacor, oxadiazon, benoxacor, dichlorprozin, flurbiproflumilast 、UBH-509、D489,LS 82-556、KPP-300、NC-324、NC-330、KH-218、DPX-N8189、SC-0744、DOWCO535、DK-8910、V-53482、PP-600、MBH-001、KIH-9201、ET-751、KIH-6127 and KIH-2023.

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

a) Dichlorophenyl pyrazoline-3-carboxylic acid (S1) compounds, preferred compounds are for example ethyl 1- (2, 4-dichlorophenyl) -5- (ethoxycarbonyl) -5-methyl-2-pyrazoline-3-carboxylate (S1-1, mefenpyr-diethyl), PM, pages 594-595, and related compounds described in for example WO91/07874 and PM (pages 594-595).

B) The dichlorophenyl pyrazole carboxylic acid derivative, preferred compounds are, for example, ethyl 1- (2, 4-dichlorophenyl) -5-methylpyrazole-3-carboxylate (S1-2), ethyl 1- (2, 4-dichlorophenyl) -5-isopropylpyrazole-3-carboxylate (S1-3), ethyl 1- (2, 4-dichlorophenyl) -5- (1, 1-dimethyl-ethyl) pyrazole-3-carboxylate (S1-4), ethyl 1- (2, 4-dichlorophenyl) -5-phenylpyrazole-3-carboxylate (S1-5), and related compounds described in EP-a-333131 and EP-a-269806.

C) Triazolecarboxylic acids (S1) are, for example, clomazone (fenchlorazole), i.e. ethyl 1- (2, 4-dichlorophenyl) -5-trichloromethyl- (1H) -1,2, 4-triazole-3-carboxylate (S1-6) and related compounds (see EP-A-174562 and EP-A-346620).

D) Preferred compounds of the 5-benzyl-or 5-phenyl-2-isoxazoline-3-carboxylic acid type or 5, 5-diphenyl-2-isoxazoline-3-carboxylic acid type are, for example, ethyl 5- (2, 4-dichlorobenzyl) -2-isoxazoline-3-carboxylate (S1-7) or ethyl 5-phenyl-2-isoxazoline-3-carboxylate (S1-8) and related compounds described in WO91/08202, or ethyl 5, 5-diphenyl-2-isoxazoline-3-carboxylate (S1-9, bisbenzoxaden-ethyl) or ethyl 5, 5-diphenyl-2-isoxazoline-3-carboxylate (S1-10) or ethyl 5- (4-fluorophenyl) -5-phenyl-2-isoxazoline-3-carboxylate (S1-11) described in the patent application (WO-A-95/07897).

E) 8-quinolinyloxyacetic acid (S2) compounds, preferably 1-methylhex-1-yl (5-chloro-8-quinolinyloxy) acetate (S2-1, detoxicated quinazolin (cloquintocet-mexyl) such as 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-allyloxyprop-2-yl (5-chloro-8-quinolinyloxy) acetate (S2-4), (5-chloro-8-quinolinyloxy) ethyl acetate (S2-5), (5-chloro-8-quinolinyloxy) acetate (S2-6), (5-chloro-8-quinolinyloxy) allyl acetate (S2-7), 2- (2-propyleneiminooxy) -1-ethyl (5-chloro-8-quinolinyloxy) acetate (S2-3), 1-allyloxyprop-2-yl (S2-5-chloro-8-quinolinyloxy) acetate (S2-6), and (EP-5-chloro-8-quinolinyloxy) acetate (S2-6) are described as (S2-5-chloro-8-quinolinyloxy) acetate and EP-5-7-2-quinolinyloxy) acetate, related compounds in EP-A-94349 and EP-A-191736 or EP-A-0492366.

F) (5-chloro-8-quinolinyloxy) malonic acid compounds, preferred compounds are diethyl (5-chloro-8-quinolinyloxy) malonate, diallyl (5-chloro-8-quinolinyloxy) malonate, (5-chloro-8-quinolinyloxy) -methylethyl malonate and related compounds described in EP-A-0582198.

G) Phenoxyacetic acid, phenoxypropionic acid or aromatic carboxylic acid-based active compounds, for example 2, 4-dichlorophenoxyacetic acid (and esters) (2, 4-D), 4-chloro-2-methylphenoxypropionate (2-methyl-4-chloropropionate)), MCPA or 3, 6-dichloro-2-methoxybenzoic acid (and esters) (dicamba).

H) Pyrimidine active compounds, such as "lyxolidine (fenclorim)" (PM, pages 386-387) (=4, 6-dichloro-2-phenylpyrimidine),

I) Dichloroacetamides active compounds, which are commonly used as pre-emergence safeners (safeners for soil), such as "dichloroacrylamide (dichloromid)" (PM, pages 270-271) (=n, N-diallyl-2, 2-dichloroacetamide), "AR-29148" (=3-dichloroacetyl-2, 5-trimethyl-1, 3-oxazolidinone, available from Stauffer), "clomazone (benoxacor)" (PM, pages 74-75) (=4-dichloroacetyl-3, 4-dihydro-3-methyl-2H-1, 4-benzoxazine), "APPG-1292" (=n-allyl-N [ (1, 3-dioxolan-2-yl) -methyl ] dichloroacetamide, from PPG Industries), "ADK-24" (=n-allyl-N- [ (allylaminocarbonyl) -methyl ] -dichloroacetamide, from Sagro-Chem), "AAD-67" or "AMON4660" (=3-dichloroacetyl-1-oxa-3-aza-spiro [4,5] decane, from Nitrokemia or Monsanto), "diclonon" or "ABAS145138" or "ALAB145138" (= (=3-dichloroacetyl-2, 5-trimethyl-1, 3-diazabicyclo [4.3.0] nonane, from BASF), and "furilazol" or "AMON13900" (see PM, 482-483) (= (RS) -3-dichloroacetyl-5- (2-furyl) -2, 2-dimethyloxazolidinone),

J) Dichloroacetone derivatives such as "AMG191" (CAS accession number 96420-72-3) (=2-dichloromethyl-2-methyl-1, 3-dioxolane, commercially available from Nitrokemia),

K) Oxyimino compounds, which are known as seed dressing materials, for example, "lyfenamic (oxabetrinil)" (PM, page 689) (= (Z) -1, 3-dioxolan-2-ylmethoxyimino (phenyl) acetonitrile), which are known as safeners in seed dressing to prevent damage to metolachlor (metolachlor), "fluroxamate (fluxofenim)" (PM, page 467-468) (= 1- (4-chlorophenyl) -2, 2-trifluoro-1-ethanone O- (1, 3-dioxolan-2-ylmethyl) -oxime, which are known as safeners in seed dressing to prevent damage to metolachlor (metolachlor), and "lyoxamic nitrile (cyometrinil)" or "a-CGA-43089" (PM, page 983) (= (Z) -cyanomethoxy imino (phenyl) acetonitrile), which are known as safeners in seed dressing to prevent damage to metolachlor (metolachlor),

L) thiazole carboxylic acid ester-based active compounds, which are known as seed dressing materials, such as "clodinafop-propargyl (flurazol)" (PM, pages 450-451) (=benzyl 2-chloro-4-trifluoromethyl-1, 3-thiazole-5-carboxylate), which are known as safeners in seed dressing to prevent damage to alachlor (alachlor) and metolachlor,

M) naphthalene dicarboxylic acid derivatives, known as seed dressing agents, for example "naphthalene dicarboxylic anhydride" (PM, pages 1009-1010) (=1, 8-naphthalene dicarboxylic anhydride), which are known as safeners in corn seed dressing to prevent damage by thiocarbamate herbicides,

N) chroman acetic acid (chromaneaceticacid) derivatives active compounds, for example, "ACL 304115" (CAS registry number 31541-57-8) (=2-84-carboxychroman-4-yl) acetic acid, from American cyanamid),

O) active compounds which have a herbicidal effect on harmful plants and also have a safener effect on plants, for example, "pimidan (DIMEPIPERATE)" or "AMY-93" (PM, pages 302 to 303) (=s-1-methyl-1-phenylethylpiperidine-1-thiocarboxylate), "diuron (daimuron)" or "ASK23" (PM, page 247) (=1- (1-methyl-1-phenylethyl) -3-p-tolylurea), "bensulfuron (cumyluron)" = "AJC-940" (=3- (2-chlorophenyl methyl) -1- (1-methyl-1-phenyl-ethyl) urea, see JP-a-60087254), "benzophenone (methoxyphenon)" or "ANK049" (=3, 3' -dimethyl-4-methoxy-benzophenone), "CSB" (=1-bromo-4- (chloromethylsulfonyl) benzene) (CAS symbol 54091-06-4, commercially available from Kumiai).

The safener is preferably one or more of bisbenzoxazole acid (CAS: 163520-33-0), cyprosulfamide (CAS: 221667-31-8), pyraclostrobin (CAS: 135590-91-9), cloquintocet-mexyl (CAS: 99607-70-2), gibberellic acid (CAS: 7-06-5), furilazole (CAS: 121776-33-8), metcamifen (CAS: 129531-12-0).

In the context of the present specification, if the abbreviated form of the generic name of the active compound is used, all customary derivatives, such as esters and salts, as well as isomers, in particular optical isomers, in particular one or more commercially available forms, are included in each case. If the generic name denotes esters or salts, all other customary derivatives are also included in each case, such as other esters and salts, free acids and neutral compounds, as well as isomers, in particular optical isomers, in particular one or more commercially available forms. The chemical name given to a compound means at least one compound covered by a common name, generally the preferred compound. In the case of sulfonamides such as sulfonylureas, salts also include salts formed by the exchange of cations with hydrogen atoms in the sulfonamide group. For example, 2-methyl-4-chloro derivatives include, but are not limited to: 2 methyl 4 chloro sodium salt, potassium salt, dimethyl ammonium salt, isopropyl amine salt, etc., 2 methyl 4 chloro methyl ester, ethyl ester, isooctyl ester, ethyl thioester, etc.; 2,4-D derivatives include, but are not limited to: 2,4-D salts such as sodium salt, potassium salt, dimethyl ammonium salt, triethanol ammonium salt, isopropyl amine salt, choline, etc., and 2,4-D esters such as methyl ester, ethyl ester, butyl ester, isooctyl ester, etc.

In the context of the present invention, the salts of the compounds are preferably the respective alkali metal salts (e.g. lithium, sodium and potassium salts), alkaline earth metal salts (e.g. calcium and magnesium salts), transition metal salts (e.g. manganese, copper, zinc and iron salts), ammonium salts or substituted ammonium in which 1 to 4 hydrogen atoms are replaced by C ₁-C₄ alkyl, hydroxy-C ₁-C₄ alkyl, C ₁-C₄ alkoxy-C ₁-C₄ alkyl, hydroxy-C ₁-C₄ alkoxy-C ₁-C₄ alkyl, phenyl or benzyl, preferably ammonium, methylammonium, isopropylammonium, dimethylammonium, diisopropylammonium, trimethylammonium, heptylammonium, dodecylammonium, tetradecylammonium, tetramethylammonium, tetraethylammonium, tetrabutylammonium, 2-hydroxyethylammonium (alkanolamine salts), 2- (2-hydroxyethan-1-oxy) ethan-1-ylamine (diglycolamine salts), di (2-hydroxyethan-1-yl) ammonium (glycol amine salts), tri (2-hydroxyethyl) ammonium (triol salts), tri (2-hydroxypropyl) ammonium, benzyltrimethylammonium, benzyltriethylammonium, N, N, N-trimethylammonium, N-trimethylsulfonium (35) and, in addition to the preferred forms of sulfonium, sulfonium (35) and sulfonium ions, sulfonium (e.g. 35, and also the preferred forms of the sulfonium, and sulfonium salts are also preferred as the preferred sulfonium (35, and sulfonium salts.

In the context of the present invention, esters of the compounds, for example as alkyl esters, alkenyl esters, alkynyl esters, alkoxyalkyl esters, tetrahydrofuranylmethyl esters and the corresponding thioesters, preference is given to C ₁-C₁₀ -alkyl esters, C ₂-C₁₀ -alkenyl esters, C ₂-C₁₀ -alkynyl esters, C ₁-C₁₀ -alkoxyC ₁-C₁₀ -alkyl esters, (tetrahydrofuran-2-yl) methyl esters and the corresponding thioesters. Preferred C ₁-C₁₀ -alkyl esters or C ₁-C₁₀ -alkylthio esters are, for example, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, pentyl, methylhexyl (1-methylhexyl), methylheptyl (1-methylheptyl), heptyl, octyl or isooctyl (2-ethylhexyl) esters. Preferred C ₁-C₁₀ alkoxy-C ₁-C₁₀ alkyl esters are C ₁-C₄ alkoxyethyl esters, for example 2-methoxyethyl, 2-ethoxyethyl, 2-butoxyethyl (butoxyethyl), 2-butoxypropyl or 3-butoxypropyl esters.

The compositions of the present invention may be diluted by the user prior to use or used directly. The preparation can be prepared by common processing method, namely, mixing the active substance with liquid solvent or solid carrier, and adding one or more surfactants such as dispersing agent, stabilizer, wetting agent, adhesive, defoamer, etc.

The specific preparation of the weeding composition is dispersible oil suspending agent, water suspending agent, suspending emulsion, wettable powder, emulsifiable concentrate, water dispersible granule (dry suspending agent), water emulsion and microemulsion.

Briefly, the compositions of the present invention can be mixed with solid and liquid additives conventionally used in prior art formulations. The amount of the active ingredient used varies with the external conditions such as temperature, humidity, the nature of the herbicide used, and the like. It may have a large variation, for example between 0.001 and 2.0kg/ha, or more, of active substance, but preferably between 0.003 and 1.0kg/ha, in particular between 5 and 500 g/ha.

The invention also provides application of the weeding composition in weed control; and a method of controlling unwanted plant growth comprising applying the herbicidal composition to plants, plant parts, plant seeds or areas of plant growth.

In addition, the compositions of the invention can be applied by spraying onto the foliage of the plants to be treated, i.e. onto weeds, in particular onto surfaces which are infested or susceptible to infestation by weeds.

When the herbicidal composition of the present invention is applied, unexpected synergistic effects are obtained, and herbicidal activity is more remarkable than the sum of the expected activities using individual herbicides, and the activity of individual herbicides. The synergistic effect is manifested by a reduced application rate, a broader weed control spectrum, a faster and more durable herbicidal action, which are desirable in the practice of weed control. These new compositions are significantly superior to existing herbicides in terms of the characteristics described, achieving reduced use and being more environmentally friendly.

The synergistic weeding composition provided by the invention also has the following advantages:

(1) The composition of the invention is environment-friendly and is easy to degrade in the environment.

(2) The weeding composition disclosed by the invention is low in cost and convenient to use, and has great economic and social benefits in popularization and application.

All patents, patent applications, and publications mentioned or cited herein are hereby incorporated by reference in their entirety to the same extent as if each individual publication was specifically and individually indicated to be incorporated by reference.

Detailed Description

The following examples are not intended to limit the invention but are merely illustrative of how the invention may be practiced. For certain weeds, these examples showed particularly significant effectiveness. Examples are as follows:

A) Examples

1.+Fenflurone (1+15) dispersible oil suspending agent

The balance is made up of +15% of fenbuconazole, 5% of calcium dodecyl benzene sulfonate, 5% of styrylphenol polyoxyethylene ether, 8% of fatty alcohol polyoxyethylene ether, 2% of organic bentonite, 2% of fumed silica, 5% of 200# solvent oil, 5% of methyl oleate and primary soybean oil

2.+Mesotrione (1+20) dispersible oil suspension

+20% Mesotrione +5% calcium dodecyl benzene sulfonate +6% styrylphenol polyoxyethylene ether +8% cardanol polyoxyethylene ether +1.5% organic bentonite +1% fumed silica +5%200# solvent oil +5% methyl oleate +first grade soybean oil make up the rest

3.+Topramezone (1+5) dispersible oil suspension

+5% Topramezone +5% calcium dodecyl benzene sulfonate +4% styrylphenol polyoxyethylene ether +6% heterogeneous fatty decaalcohol polyoxyethylene ether +3% organic bentonite +2% fumed silica +5%200# solvent oil + methyl oleate make up the balance

4.+Isoxaflutole (1+15) dispersible oil suspending agent

+15% Of isoxaflutole +6% of calcium dodecyl benzene sulfonate +6% of fatty acid polyoxyethylene ester +5.5% of polyoxyethylene sorbitan fatty acid ester +2.5% of organic bentonite +2% of fumed silica +5% of 200# solvent oil + methyl oleate make up the balance

5.+Fluroxypyr (1+15) dispersible oil suspension

The balance is +15% fluopicolide +5.8% calcium dodecyl benzene sulfonate +8.2% styrylphenol polyoxyethylene ether +7% cardanol polyoxyethylene ether +2% organic bentonite +2% fumed silica +5%200# solvent oil +methyl oleate

6.+ Tolpyralate (1+50) water dispersible granule

+50% Tolpyralate+5% precipitation white carbon+5% alkyl naphthalene sulfonate formaldehyde polycondensate sodium salt+3% Morwet EFW+2.5% sodium lignin sulfonate+10% corn starch+10% ammonium sulfate+kaolin

7.+Nicosulfuron (1+10) dispersible oil suspension

The balance of +10% nicosulfuron +7.2% calcium dodecyl benzene sulfonate +3.3% heterogeneous fatty deca-alcohol polyoxyethylene ether +10% cardanol polyoxyethylene ether +2.8% organic bentonite +2% fumed silica +methyl oleate

8.+Foramsulfuron (1+10) dispersible oil suspension

10% Of formamide sulfolane, 7.5% of dodecyl benzene sulfonic acid calcium, 8.5% of polyoxyethylene sorbitan fatty acid ester, 3% of trivinyl phenol polyoxyethylene polyoxypropylene ether, 3% of organic bentonite, 2% of fumed silica and primary soybean oil are used for the balance

9.+Atrazine (0.5+62.5) water dispersible granule

+62.5% Atrazine+5% precipitated silica+3% GY-D800+2% GY-W04+2% sodium lignin sulfonate+8% sucrose+urea

10.+Terbuthylazine (1+75) water dispersible granule

+75% Terbuthylazine +4% alkyl naphthalene sulfonate formaldehyde polycondensate +2% nekal +1% sodium lignin sulfonate +5% corn starch +0.05% xanthan gum + ammonium sulfate make up

The dispersible oil suspending agent processing equipment comprises: mixing kettle, colloid mill, sand mill, shearing machine, etc.

The processing process of the dispersible oil suspending agent comprises the following steps: all materials are put into a mixing kettle, stirred and mixed, then the materials are subjected to a colloid mill, and finally enter a sand mill for three-stage sand milling, finally the materials are uniformly sheared in a shearing machine, and after the materials are tested to be qualified, the materials are transferred to a storage tank for filling.

Above-mentioned water dispersible granule processing equipment: mechanical pulverizer, jet mill, coulter mixer, basket granulator, drying oven, sieving machine, etc.

The processing process of the water dispersible granule comprises the following steps: after the materials are uniformly mixed, mechanical crushing is carried out, then airflow crushing is carried out, water is added for uniform mixing, then kneading granulation is carried out, drying and granulating are carried out after granulation, and finally screening is carried out, thus obtaining the finished product.

B) Test of efficacy

Post-emergence stem and leaf spray treatment:

1) Test conditions

1.1 Test target): herb of Fangbao

Culturing weeds by a potting method, placing the weeds in a plastic nutrition pot with the diameter of 180 х mm in a enamel tray, arranging surface soil (4/5) which is collected from farmlands and air-dried and sieved, controlling the initial stage of soil humidity to be 20%, selecting weed seeds with full and uniform seeds, soaking the weed seeds in warm water at 25 ℃ for 6 hours, accelerating germination in a biochemical incubator (dark) at 28 ℃, uniformly placing the just-exposed weed seeds on the surface of the soil, and then covering the soil by 0.5-1cm according to the particle size of the seeds.

1.2 Culture conditions

The method is carried out in a controllable sunlight greenhouse, the temperature is 20-30 ℃, natural illumination is carried out, and the relative humidity is 57-72%. The soil type is loam, the organic matter content is 1.63%, the pH=7.1, the alkaline hydrolysis nitrogen content is 84.3mg/kg, the quick-acting phosphorus content is 38.5mg/kg, and the quick-acting potassium content is 82.1mg/kg.

1.3 Instrument and equipment

3WP-2000 type walking spray tower (Nanjing agricultural machinery institute of agricultural division); GA0 model ten-thousandth electronic balance (germany); ZDR2000 intelligent data logger (zengzhuze instruments limited); SPX intelligent biochemical incubator (Ningbo Jiangnan instruments factory).

2) Test design

2.1 Reagents)

The required active ingredientsFrom patent CN201810729510.0; the desired active ingredient B is purchased from the reagent company or is synthetically prepared according to conventional methods. The raw materials are all diluted by using acetone as solvent and 0.1% of emulsifier Tween-80 aqueous solution, and the diluted materials are diluted at present.

2.2 Test treatment

2.2.1 Dose setting)

In determining the ratio or content of A and active ingredient B, the main purpose of the formulation should be considered in consideration of the action characteristics of the two medicaments and the toxicity thereof. The study was based on the preliminary pre-test, and the single use and the mixed use of A, B active ingredients are shown in the table. Water without agent, with the same solvent and emulsifier was used as a blank.

2.2.2 Test repetition

Each treatment was repeated 4 times, 3 pots each, 20 seeds of weed seeds were sown per pot, 60 plants per treatment.

2.3 Processing mode)

2.3.1 Time and number of treatments

The test was performed 1 time. And (3) after 1.5-2 leaves of weeds are in a period of thinning, 10 plants of weeds in each pot are maintained, 30 plants are maintained for each treatment, and then cultivation is continued until 3-4 leaves are subjected to treatment.

2.3.2 Device and method of administration

The cultured test materials are evenly placed on a platform with the area of 0.5m ², and sprayed by a 3WP-2000 type walking spray tower, wherein the spraying pressure is 0.3MPa according to the spraying amount of 450 kg/hectare. After all the liquid medicine is sprayed, the air valve is closed, the spraying tower door is opened after 30 seconds, and the nutrition pot is taken out. Then the air valve is opened, 50mL of clean water is sprayed, and the liquid spraying pipe is cleaned.

3) Test method

Potting method is adopted. Weed cultivation is 1.1), and is carried out by referring to herbicide as a rule of biological assay in pesticide room. The application method is 2.3.2), and stem and leaf treatment is adopted. After treatment, the cells are transferred into a greenhouse for routine cultivation.

4) Data investigation and statistical analysis

4.1 Investigation method)

The entire seedlings of surviving weeds were cut off along the soil surface with a blade by an absolute number survey method, and the fresh weight of weeds was weighed with an analytical balance. For weeds that have died, the fresh weight is zero.

4.2 Time and number of surveys

The investigation was performed 14 days after the treatment, 1 total time.

4.3 Data statistics analysis

The theoretical fresh weight inhibition rate (E0=X+Y-X X Y/100) of each treatment mixed combination is calculated by Gowing method, then compared with the actual measurement inhibition rate (E), the combined action type of the two mixed combinations on weeds is evaluated, and when the E-E0 value is more than 10% and is synergistic, less than-10% is antagonistic, and between-10% and 10% is additive. And determining the optimal proportion according to the actual control effect, the characteristics of herbicide, the balance of the formula and other factors. Wherein X is 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.

The statistical results are shown in tables 1-10 below.

Table 1A evaluation of actual control and Combined Effect of Benzoinum-fluroxypyr on Fabry-Perot

Table 2A evaluation of actual control and Combined Effect of mesotrione on Fangbao grass

Table 3A evaluation of actual control and Combined Effect of topramezone on Fangbao grass

Table 4A evaluation of actual control and Combined Effect of Isoxadiazon on Fangbao grass

Table 5A evaluation of actual control and Combined Effect of Fluopicolone on Fangcao

Table 6A evaluation of actual control and Combined Effect of Compound Tolpyralate on Fangcao

Table 7A evaluation of actual control and Combined Effect of Mixed nicosulfuron on Pacific grass

Table 8A evaluation of actual control and Combined Effect of compounded foramsulfuron on Fangcao

Table 9A evaluation of actual control and Combined Effect of atrazine compounded on Pacific weeds

Table 10A evaluation of actual control and Combined Effect of terbuthylazine on Fangcao

C) Demonstration of field

The herbicidal compositions prepared in examples 1 to 10 above were used for field weed effect tests. Weeds occurring in the field are mainly: grass of Fangbao, commelina communis, herba Chenopodii, etc.

The test method comprises the following steps:

Stem and leaf treatment (F): when weeds are in the 3-4 leaf stage, a manual sprayer is used, the water adding amount is 30 kg/667 m ², and stem and leaf spraying is adopted for uniform spraying. The effect of controlling and preventing was examined 45 days after the application and is shown in Table 11.

Exemplary field effects of the formulated compositions described in Table 11

Through a large number of experiments and researches, the composition is unexpectedly found that the composition is used for preventing and killing main broadleaf weeds or grassy weeds and the like, has a surprising and unexpected synergistic effect, has more remarkable synergistic effect under low dosage, can reduce the dosage, reduces the pollution to the environment, reduces the agricultural cost through reasonable compounding, and has good application prospect.

Claims (10)

1. A herbicidal composition comprising a substituted pyrimidine formyl oxime compound, which is characterized by comprising a herbicidally effective amount of an active ingredient A and an active ingredient B, wherein,

The active component A is

The active ingredient B is selected from one or more of the following compounds: topramezone, mesotrione, topramezone, isoxaflutole, fluopicolone, tolpyralate, nicosulfuron, foramsulfuron, atrazine, terbuthylazine.

2. The herbicidal composition comprising a substituted pyrimidine formyl oxime compound according to claim 1, wherein the weight ratio of A, B in the herbicidal composition is 1:300 to 50:1, 1:250 to 20:1, 1:200 to 10:1, 1:160 to 5:1, 1:100 to 3:1, 1:60 to 1:1, 1:50 to 1:3, 1:30 to 1:5 or 1:20 to 1:10.

3. A herbicidal composition comprising a substituted pyrimidine formyl oxime compound according to claim 1, wherein active ingredient a isThe active ingredient B is selected from one or more of the following compounds: the weight ratio of A, B in the weeding composition is 1:30-1:1, preferably 1:20-4:5;

The active component A is The active ingredient B is topramezone, and the weight ratio of A, B in the weeding composition is 1:10-5:1, preferably 1:6-8:3;

The active component A is The active component B is Tolpyralate, and the weight ratio of A, B in the weeding composition is 1:70-1:1, preferably 1:50-8:25;

The active component A is The active ingredient B is selected from one or more of the following compounds: the weight ratio of A, B in the weeding composition is 1:20-5:1, preferably 1:10-2:1;

The active component A is The active ingredient B is selected from one or more of the following compounds: the weight ratio of A, B in the weeding composition is 1:250-1:5, preferably 1:200-1:10.

4. Herbicidal composition comprising substituted pyrimidine formyl oximes according to claim 1, characterized in that the herbicidal composition comprises 1 to 95% by mass, preferably 1 to 80% by mass of a and B in total.

5. A herbicidal composition comprising a substituted pyrimidine formyl oxime compound according to any of claims 1 to 4 wherein said herbicidal composition further comprises conventional adjuvants, preferably said conventional adjuvants comprise carriers and/or surfactants.

6. A herbicidal composition comprising a substituted pyrimidine formyl oxime compound according to any of claims 1 to 4, wherein said herbicidal composition further comprises at least one safener.

7. The herbicidal composition comprising a substituted pyrimidine formyl oxime compound according to claim 6, wherein said safener is selected from one or more of bisbenzoxazole acid, cyprosulfamide, pyraclonil, cloquintocet-mexyl, gibberellic acid, furilazole, metcamifen.

8. The herbicidal composition comprising a substituted pyrimidine formyl oxime compound according to any one of claims 1 to 4, wherein the specific formulation of the herbicidal composition is a dispersible oil suspension, an aqueous suspension, a suspoemulsion, a wettable powder, an emulsifiable concentrate, a water dispersible granule, an aqueous emulsion or a microemulsion.

9. Use of a herbicidal composition comprising a substituted pyrimidine formyl oxime compound according to any of claims 1 to 8 for the control of weeds.

10. A method of controlling unwanted vegetation which comprises applying the herbicidal composition comprising an oxyiminoaryl compound of the substituted pyrimidine formyl oximes of any one of claims 1 to 8 to plants, plant parts, plant seeds or areas of vegetation.