CN117658998A - Herbicidal compositions comprising R-pyridyloxycarboxylic acid derivatives and use thereof - Google Patents

Herbicidal compositions comprising R-pyridyloxycarboxylic acid derivatives and use thereof Download PDF

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CN117658998A
CN117658998A CN202211093386.6A CN202211093386A CN117658998A CN 117658998 A CN117658998 A CN 117658998A CN 202211093386 A CN202211093386 A CN 202211093386A CN 117658998 A CN117658998 A CN 117658998A
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herbicidal composition
acid derivative
type
pyridyloxycarboxylic
active ingredient
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王恒智
李平生
崔琦
刘伟堂
王金信
路兴涛
陈爽
王鹏
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Qingdao Kingagroot Chemical Compound Co Ltd
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Qingdao Kingagroot Chemical Compound Co Ltd
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Abstract

The invention belongs to the field of pesticides, and particularly relates to a weeding composition containing an R-type pyridyloxycarboxylic acid derivative 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 R-pyridyloxycarboxylic acid derivatives and use thereof
Technical Field
The invention belongs to the field of pesticides, and particularly relates to a weeding composition containing an R-type pyridyloxycarboxylic acid derivative 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 above-mentioned problems occurring in the prior art, the present invention provides a herbicidal composition comprising an R-type pyridyloxycarboxylic acid derivative. The composition can effectively prevent and remove grassy weeds or broadleaf 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 an R-type pyridyloxycarboxylic acid derivative 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: cycloxazinone (CAS: 51235-04-2), buthiuron (CAS: 34014-18-1), simazine (CAS: 122-34-9), triclopyr (CAS: 314-40-9), and ametryn (CAS: 834-12-8).
Wherein the weight ratio of A to B in the weeding composition is 1:30-30:1, 1:20-20:1, 1:10-10:1, 1:8-8:1, 1:6-6:1, 1:4-4:1, 1:3-3:1 or 1:1-2:1.
The mass percentage of A and B in the weeding composition accounts for 1-95% of the total amount, preferably 10-80%.
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, national 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, prometryn, chlor, cola, prometryn, fluben, prometryn, fluben, atractyl, bentazone, liquorice, cyanuric acid, indoziflam, chlorsulfuron, metsulfuron, bensulfuron methyl, chlorimuron ethyl, tribenuron methyl, thisulfuron methyl, pyrazosulfuron ethyl, mesosulfuron methyl, sodium methyl iodosulfuron, formaminosulfuron methyl, cinosulfuron methyl, mesosulfuron methyl, 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, carboxin, trifluoperal, methoxybenomyl, trinitrofen, fluorobenomyl, fluroxypyr-meptyl, herbicidal ether, pyriftalid, halofop-butyl, chlortoluron, isoproturon, linuron, diuron, sepromon, flubenuron, thifenuron, metsulfuron-methyl, trifloxystrobin 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, tetrafluorone, phenytoin, betanin-ethyl, betanin, sulbenazolin, terbutryn, avenanthramide, anil, chloranil, penoxsulam, clodinafop-propargyl, carboxazole, chlorprocarb, fenasulam, BCPC, CPPC, carbasulam, butachlor, graminium, imago, graminite, imazamox, pethaline, graminium, pyrifos, avenanthramide, thiofide, captan, kexiang, benfop-butyl, secondary sudan, thiomethodan, benazolan, isopolinate, methiobencarb, 2,4-D isooctyl butyl, 2,4-D isooctyl sodium chloride, 2,4-D isooctyl sodium salt, 2,4-D isooctyl dimethylamine salt, 2,4-D ethoxysulfate, 2,4-D isooctyl propionic acid, high 2,4-D isooctyl salt, 2,4-D isooctyl butyric acid, 2,4-D chloropropionic 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, imago, valicarb, triamcinolone, amisulbenac, trimethoprim, sethoxydim, fluazifop-p-butyl, haloxyfop-butyl, quizalofop-p-ethyl, quizalofop-ethyl, oxazalofop-p-ethyl, fenoxaprop-p-ethyl, oxazalofop-ethyl, cyhalofop-butyl, haloxyfop-butyl oxazophos, clodinafop-propargyl, thiazate, propargyl, hydroxyvalerate, trifluoperazone, clomazone, paraquat, diquat, ambroxol, buprofezin, ethambutol, isoproturon, sultriad, ciprofloxacin, aminoprofloxacin, benfurin, halofop-butyl, amino ethyl, dilefol, clodinafop-butyl, methalproplin, prochloraz, 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, haloxyfop, triclopyr, buprofezin, fluroxypyr, clopyralid, diflufenzopyr, butoxyethyl triclopyr, cliodinate, sethoxydim, clethodim, thioxanthone, gramoxydim, fenpropion, trifloxystrobin, pyrone, buthidazole, metribuzin, buprofezin, oxazidone, buprofezin, ametridione, amibuzin, bromoxynil octanoate, xin Xiandian benzonitrile, ioxynil Dithalonitrile, diphenylacetonitrile, biscarfentrazone-ethyl, hydroxydichlorvos, iodobonil, flumetsulam, florasulam, penoxsulam, sulfentrazone-ethyl, clomazone, pyriftalid, pyroxsulam, trifluoperazone, fluben, bispyriftalid, pyriftalid, bicyclosultone, mesotrione, sulfentrazone, tembotrione, tefuryltrione, bicyclopyrone, ketodpiradox, isoxaflutole, clomazone, fenoxasulfone, methiozolin, penoxsulam, pyriftalid pyriproxyfen, pyrazolote, delphinium, benoxadiazon, pyribenzoxim, pyrasulfuron, topramezone, pyroxasulfone, flumetsulam, carfentrazone-ethyl, amicarbazone, carfentrazone-ethyl, fenpyrad-ethyl, fenitron-methyl, sulfentrazone, bencarbazone, bupirimate, flumetsulam, triclopyr, terfenacet, fluaropacil, indoxacarb, flumetofen, flumetsulam, clomazone, triclopyr, fenpropidium, and fenpropidium, phtalol, flumezin, pentachlorophenol (sodium), dinol, terfenacil, ter Le Zhi, pentanitrophenol, dinitrate, chloronitrophenol, dilarol, propisochlor, oxadiazon, cyclopentaoxadiazon, flumetsulam, methyl oxazinate, tebuconazole, fluidazinate, chlorpyrim, chlorpyrifos, dimethomorph, pyridylether, pyridazone, bentazone, pyridaph, pyridafos, quinclorac, clorac, bentazone, pyridate, oxazinone, benazolin, clomazone, isopropyl ether, propisochlor, indenone, sodium chlorate, coumoxystrobin, trichloroacetic acid, monochloroacetic acid, hexachloroacetone, tetrafluoropropionic acid, forage grass bromphenol oxime, triazolesulfone, mefenacet, furbenoxadone, furfurben, flumetsulam, clomazone, fludioxonil, barnyard grass, acrolein, benoxaden, mefenacet, oat ester, thiodiazole, gossypine, oxycodone, metrafenone, saflufenacil, chlor, triclopyr, alorac, diethamquat, etnipromid, iprymidam, ipfencarbazone, thiencarbazone-methyl, pyrimisulfan, chlorflurazole, tripropindan, sulglycapin, metalaxyl, trifluralin, fenitrothion, fenitron, fenugreek, ben, and the like Cambendichlor, cyprodinil, thiocyanidine, clomazone, cloquintocet-mexyl, clomazone, meflozin, mefenoxam, furazolidone, triflumuron, diflufenican, fluroxypyr, DOW chlorofluoropyridine, 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, cloquintocet-mexyl) such as PM (page 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 methyl (S2-6), (5-chloro-8-quinolinyloxy) acetate (S2-7), 2- (2-propyleneiminooxy) -1-ethyl (5-chloro-8-quinolinyloxy) acetate (S2-4), and (S2-chloro-8-quinolinyloxy) acetate (S2-6) are described as (S2-chloro-8-quinolinyloxy) acetate (S2-4), (5-chloro-8-quinolinyloxy) acetate (S2-6), and (2-chloro-8-quinolinyloxy) acetate (S2-ethyl acetate (2-chloro-quinolyl) 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" (PM, pages 386-387) (=4, 6-dichloro-2-phenylpyrimidine),
i) Dichloroacetamides are commonly used as pre-emergence safeners (safeners for soil), for example "dichloroacrylamide (dichlormid)" (PM, pages 270-271) (=n, N-diallyl-2, 2-dichloroacetamide), "AR-29148" (=3-dichloroacetyl-2, 5-trimethyl-1, 3-oxazolidinone, available from Stauffer), "oxazin (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, available from PPG Industries), "ADK-24" (=n-allyl-N- [ (allylaminocarbonyl) -methyl ] -dichloroacetamide, available from Sagro-Chem), "AAD-67" or "AMON4660" (=3-dichloroacetyl-1-oxa-3-aza-spiro [4,5] decane, available from Nitrokemia or Monsanto), "dicylon" or "ABAS145138" or "ALAB145138" (= (=3-dichloroacetyl-2, 5-trimethyl-1, 3-diazabicyclo [4.3.0] nonane, available 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 registry number 96420-72-3) (=2-dichloromethyl-2-methyl-1, 3-dioxolane, available from Nitrokemia),
k) Oxyimino compounds, which are known as seed dressing materials, for example, "oxadiazon (oxaberil)" (PM, page 689) (= (Z) -1, 3-dioxolan-2-ylmethoxyimino (phenyl) acetonitrile), which are known as safeners in seed dressing to prevent damage to metolachlor (metazachlor), which are known as safeners in seed dressing to prevent damage to metolachlor (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 (metazachlor), and "metolachlor (cymettrinil)" or "a-CGA-43089" (PM, page 983) (= (Z) -cyanomethoxy imino (phenyl) acetonitrile),
l) thiazole carboxylic acid ester-based active compounds, which are known as seed dressing materials, such as "clomazone" (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 (chroman acetic acid) derivatives like, 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 herbicidal action on harmful plants and also safener action on plants, for example, "pimidan (dimeprate)" or "AMY-93" (PM, pages 302 to 303) (=s-1-methyl-1-phenylethylpiperidine-1-thiocarboxylate), "daimuron" or "ASK23" (PM, page 247) (=1- (1-methyl-1-phenylethyl) -3-p-tolylurea), "bensulfuron (cumylron)," 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 "((CAS-1-bromo-4- (chloromethylsulfonyl) benzene) (54091-ai=from the trade name of kuai).
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), metacam (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 (such as lithium, sodium and potassium salts), alkaline earth metal salts (such as calcium and magnesium salts), transition metal salts (such as manganese, copper, zinc and iron salts), ammonium salts or salts in which 1 to 4 hydrogen atoms are replaced by C 1 -C 4 Alkyl, hydroxy-C 1 -C 4 Alkyl, C 1 -C 4 alkoxy-C 1 -C 4 Alkyl, hydroxy-C 1 -C 4 alkoxy-C 1 -C 4 Substituted ammonium substituted by alkyl, phenyl or benzyl, preferably ammonium, methylammonium, isopropylammonium, dimethylammonium, diisopropylammonium, trimethylammonium, heptylammonium, dodecylammonium, tetradecylammonium, tetramethylammonium, tetraethylammonium, tetrabutylammonium, 2-hydroxyethylammonium (alkanolamine salt), 2- (2-hydroxyethan-1-yloxy) ethan-1-ylammonium (diglycolamine salt), di (2-hydroxyethan-1-yl) ammonium (glycol amine salt), tri (2-hydroxyethan) ammonium (triol amine salt), tri (2-hydroxypropyl) ammonium, benzyltrimethylammonium, benzyltriethylammonium, N, N, N-trimethylethanolamine (choline salt), in addition to phosphonium ions, sulfonium ions, preferably tri (C) 1 -C 4 Alkyl) sulfonium, such as trimethylsulfonium, and sulfoxonium ions, preferably tris (C) 1 -C 4 Alkyl) sulfoxonium and finally also the form of salts of polyamines such as N, N-di (3-aminopropyl) methylamine and diethylenetriamine.
In the context of the present invention, esters of compounds, for example as alkyl esters, alkenyl esters, alkynyl esters, alkoxyalkyl esters, tetrahydrofuranylmethyl esters and the corresponding thioesters, preferably C 1 -C 10 Alkyl esters, C 2 -C 10 Alkenyl esters, C 2 -C 10 Alkynyl esters, C 1 -C 10 Alkoxy C 1 -C 10 Alkyl esters, (tetrahydrofuran-2-yl) methyl esters and the corresponding thioesters. Preferred C 1 -C 10 Alkyl esters or C 1 -C 10 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 -C 10 alkoxy-C 1 -C 10 Alkyl esters being C 1 -C 4 Alkoxyethyl esters, such as 2-methoxyethyl, 2-ethoxyethyl, 2-butoxyethyl (butoxyethyl), 2-butoxypropyl or 3-butoxypropyl ester.
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
A+Cyclooxazinone (3+15) dispersible oil suspension
The composition is prepared from 3% of A+15% of hexazinone, 5% of calcium dodecyl benzene sulfonate, 6% of fatty acid polyoxyethylene ester, 6% of cardanol polyoxyethylene ether, 2% of oleic acid triglyceride polyoxyethylene ether, 2% of organic bentonite, 2% of gas-phase white carbon black, 8% of 150# solvent oil and mixed fatty acid methyl ester
A+buthiuron (3+6) dispersible oil suspending agent
The composition is prepared from 3% of A+6% of buthiuron, 5% of calcium dodecyl benzene sulfonate, 8% of fatty acid polyoxyethylene ester, 6% of cardanol polyoxyethylene ether, 2.5% of organic bentonite, 2% of fumed silica, 8% of 150# solvent oil and mixed fatty acid methyl ester
A+Simazine (3+12) dispersible oil suspension
The composition is prepared from 3% of A+12% of simazine+5% of calcium dodecyl benzene sulfonate+8% of fatty acid polyoxyethylene ester+6% of cardanol polyoxyethylene ether+2.2% of organic bentonite+2.2% of fumed silica+8% of 150# solvent oil and mixed fatty acid methyl ester
A+herbicidal (3+20) dispersible oil suspensions
3% A+20% of triclopyr+5% of calcium dodecyl benzene sulfonate+8% of fatty acid polyoxyethylene ester+4% of cardanol polyoxyethylene ether+4% of oleic acid triglyceride polyoxyethylene ether+1.5% of organic bentonite+1.5% of fumed silica+5% of 150# solvent oil+primary soybean oil
A+ametryn (3+8) dispersible oil suspending agent
3 percent of A+8 percent of ametryn+5 percent of calcium dodecyl benzene sulfonate+7 percent of fatty acid polyoxyethylene ester+6 percent of cardanol polyoxyethylene ether+2.5 percent of organic bentonite+2.5 percent of fumed silica+5 percent of 150# solvent oil+mixed fatty acid methyl ester are complemented
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.
B) Test of efficacy
Post-emergence stem and leaf spray treatment:
1) Test conditions
1.1 Test target)
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 in the tray, 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 preparation method of the required active ingredient A is disclosed in patent CN201911321469.4; 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 pre-test at the early stage, and the single use and the mixed use of A, B active ingredients are respectively 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
Uniformly placing the cultured test material in an area of 0.5m 2 Spraying with 3WP-2000 type walking spray tower with spray amount of 450 kg/cmThe spraying pressure was 0.3MPa. 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 21 days after the treatment, 1 total.
4.3 Data statistics analysis
Calculating the theoretical fresh weight inhibition rate (E0=X+Y-X X Y/100) of each treatment mixed combination by using a Gowing method, and then comparing the calculated fresh weight inhibition rate with the measured inhibition rate (E), evaluating the combined action type of the mixed combination of the calculated fresh weight inhibition rate and the measured inhibition rate on weeds, wherein when the E-E0 value is more than 10 percent, the E-E0 value is less than-10 percent, the E-E value is antagonistic, and the E-E0 value is addition between-10 percent and 10 percent. 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.
Soil sealing treatment:
1) Test conditions
1.1 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 55-75%.
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. The test soil was quantitatively loaded to 3/4 of the pot, and then irrigated from the bottom of the pot to completely wet the soil to a saturated state. The weed seeds to be tested are subjected to germination accelerating treatment until the weed seeds are exposed to white, then uniformly and quantitatively broadcast on the surface, and soil is covered by 0.5-1cm according to the size of the seeds, and the weed seeds are sowed for later use for 72 hours.
1.2 Instrument and equipment
GA10 model ten-thousandth electronic balance (germany); ZDR2000 intelligent data logger (zengzhuze instruments limited); SPX intelligent biochemical incubator (Ningbo Jiangnan Instrument factory), pipettor, etc.
2) Test design
2.1 Reagents)
2.1.1 Test agent
The preparation method of the required active ingredient A is disclosed in patent CN201911321469.4; 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 proportion or content of each component of the A and the active ingredient B, the main purpose of the formulation should be considered according to the action characteristics of the two medicaments, the toxicity and other measures. The study was based on the pre-test at the early stage, and the single use and the mixed use of A, B active ingredients are respectively 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 time, each pot was sown with 30 weed seeds.
3) Test method
Irrigation was carried out before treatment, and a 1-2cm aqueous layer was maintained. Taking quantitative liquid medicine by a liquid shifter, and respectively irrigating from low dose to high dose according to test design, wherein each treatment is repeated for 4 times; after treatment, the cells were transferred to a greenhouse for routine cultivation, and a 1-2cm aqueous layer was maintained throughout the test period.
4) Data investigation and statistical analysis
The spraying treatment is the same as that of the stem and leaf after seedling, so the description is omitted.
The statistical results are shown in tables 1-5 below, and the other results are "post-seedling stem and leaf spray treatment" except for the clear mark "soil treatment".
Table 1A evaluation of actual control and combined action of formulated hexazinone on Euphorbia helioscopia
Table 2A evaluation of actual control and combined action of Mixed tebuthiuron on euphorbia
Table 3A evaluation of actual control and Combined action of Simazine on Acalypha australis (soil treatment)
Table 4A evaluation of actual control and combined action of compounded herbicide on euphorbia
Table 5A evaluation of actual control and combined action of compounded ametryn on Euphorbia helioscopia
C) Demonstration of field
The herbicidal compositions prepared in examples 1 to 5 above were used for field weed effect tests. Weeds occurring in the field are mainly: crabgrass, goosegrass, barnyard grass, green bristlegrass, wild millet, amaranth, acalypha australis, erigeron breviscapus and the like.
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 for adding 30 kg/667 m water 2 The stem and leaf spray is adopted for uniform spraying.
Soil treatment (S): before the germination of weeds, the manual sprayer is added with water of 45 kg/667 m 2 Soil surface spraying is adopted.
The specific test agents and dosages are detailed in Table 6, with a cell area of 50 square meters and 3 replicates per treatment. The investigation and control effects 45 days after the application are shown in Table 6.
Exemplary field effects of the formulated compositions described in Table 6
Examples Dosage (g a.i./ha) Treatment mode Fresh weight control effect%
1 2700 F 96.5
2 1350 F 98.7
3 2250 S 94.8
4 3450 F 99.3
5 1650 F 94.4
Through a large number of experiments and researches, the composition is unexpectedly found that the composition is used for preventing and killing main gramineous weeds or broadleaf 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 an R-type pyridyloxycarboxylic acid derivative, 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: hexazinone, buthiuron, simazine, triclopyr or ametryn.
2. The herbicidal composition comprising an R-type pyridyloxycarboxylic acid derivative of claim 1 wherein the herbicidal composition has a weight ratio of A, B of 1:30 to 30:1, 1:20 to 20:1, 1:10 to 10:1, 1:8 to 8:1, 1:6 to 6:1, 1:4 to 4:1, 1:3 to 3:1, or 1:1 to 2:1.
3. Herbicidal composition comprising an R-pyridyloxycarboxylic acid derivative according to claim 1, wherein the herbicidal composition comprises 1 to 95% by mass, preferably 10 to 80% by mass of a and B in total.
4.A herbicidal composition comprising an R-type pyridyloxycarboxylic acid derivative according to any one of claims 1 to 3 further comprising a conventional adjuvant.
5.A herbicidal composition comprising an R-type pyridyloxycarboxylic acid derivative according to claim 4 wherein the conventional adjuvant comprises a carrier and/or a surfactant.
6. A herbicidal composition comprising an R-type pyridyloxycarboxylic acid derivative according to any one of claims 1 to 3 further comprising at least one safener.
7. A herbicidal composition comprising an R-type pyridyloxycarboxylic acid derivative according to claim 6 wherein the safener is selected from one or more of bisbenzoxazole acid, cyprosulfamide, mequindox, cloquintocet-mexyl, gibberellic acid, furilazole, metcamifen.
8. A herbicidal composition comprising an R-type pyridyloxycarboxylic acid derivative according to any one of claims 1 to 3 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 an R-type pyridyloxycarboxylic acid derivative according to any one of claims 1 to 8 for controlling weeds.
10. A method of controlling unwanted plant growth, which comprises applying the herbicidal composition comprising an R-type pyridyloxycarboxylic acid derivative of any one of claims 1 to 8 to plants, plant parts, plant seeds or areas where plants grow.
CN202211093386.6A 2022-09-08 2022-09-08 Herbicidal compositions comprising R-pyridyloxycarboxylic acid derivatives and use thereof Pending CN117658998A (en)

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