A herbicidal composition comprising a pyrimidyl carboxyl oxime derivative and use thereof

By combining pyrimidine formyl oxime derivatives with multiple herbicides, the problem of weed resistance caused by single herbicides has been solved, achieving effective control of multiple weeds and reducing the amount of herbicide used, thus enhancing the weeding effect.

CN116965414BActive Publication Date: 2025-12-30QINGDAO KINGAGROOT RESISTANT WEED MANAGEMENT CO LTD
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Patent Information

Application Number
CN202210420582.3
Authority / Receiving Office
CN · China
Patent Type
Patents(China)
Current Assignee / Owner
Filing Date
2022-04-21
Publication Date
2025-12-30
Estimated Expiration
2042-04-21

AI Technical Summary

Technical Problem

Long-term use of single chemical herbicides has led to the evolution of herbicide resistance and tolerance in weeds. Existing herbicidal compositions are difficult to effectively control a variety of weeds and require large application rates.

Method used

Combining pyrimidine formyl oxime derivatives with herbicides of various modes of action, including HPPD inhibitors and PDS inhibitors, can broaden the weed control spectrum and reduce the application rate through synergistic effects of different mechanisms.

Benefits of technology

It effectively controls grasses and broadleaf weeds, broadens the spectrum of weed control, reduces the amount of herbicide required, solves the problem of resistant weeds, and enhances the weeding effect.

✦ Generated by Eureka AI based on patent content.

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Abstract

The present application belongs to the field of pesticides, and particularly relates to a herbicidal composition containing a pyrimidine formyl oxime derivative and application thereof. The composition comprises a herbicidally effective amount of active ingredient A and active ingredient B, wherein the active ingredient A is or a salt thereof; the active ingredient B is selected from one or more of the following compounds and acids / salts / esters thereof: HPPD inhibitors, PDS inhibitors, DOXP inhibitors, ALS inhibitors, ACCase inhibitors, PPO inhibitors, PSII inhibitors, micro assembly inhibitors, synthetic hormone inhibitors, VLCFA inhibitors, lipid synthesis (non-acetyl coenzyme A carboxylase) inhibitors, EPSPS inhibitors, GS inhibitors and the like. The composition can effectively control / repel various weeds and the like, 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.
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Description

Technical Field

[0001] This invention belongs to the field of pesticides, specifically relating to a herbicidal composition comprising a pyrimidine formyl oxime derivative and its application. Background Technology

[0002] Chemical weed control is the most economical and effective means of weed control in farmland. However, long-term, continuous, and high-dose use of single-variety or single-mode chemical herbicides can easily lead to problems such as weed resistance and the evolution of resistance. The rational combination or mixing of herbicide compounds has advantages such as broadening the weed control spectrum, improving control efficacy, and delaying the occurrence and development of weed resistance. It is one of the most effective methods to solve the above problems. However, in production, there is still a need to develop herbicide compositions with high safety, broad weed control spectrum, synergistic effects, and the ability to address resistant weeds. Summary of the Invention

[0003] To address the aforementioned problems in the prior art, this invention provides a herbicidal composition comprising a pyrimidine formyl oxime derivative and its application. This composition effectively controls / prevents grasses and broadleaf weeds, and features a broadened weed control spectrum, reduced application rate, synergistic effect, and the ability to combat resistant weeds.

[0004] A herbicidal composition comprising a pyrimidine formyl oxime derivative, comprising herbicidally effective amounts of active ingredient A and active ingredient B, wherein,

[0005] Active ingredient A is or its salt;

[0006] Active ingredient B is selected from one or more of the following compounds and their acids / salts / esters:

[0007] (1) HPPD inhibitors: Bisoxane (CAS No.: 1622908-18-2), Cyclopyralid (CAS No.: 1855929-45-1);

[0008] (2) PDS inhibitors: fluroxypyr (CAS No.: 83164-33-4), fluroxypyr (CAS No.: 137641-05-5), Beflubutamid-M (CAS No.: 113614-09-8);

[0009] (3) DOXP inhibitor: dichloroisoxamethonium (CAS No.: 81777-95-9),

[0010] (4) ALS inhibitors: bensulfuron-methyl (CAS No.: 101200-48-0), bensulfuron-methyl (CAS No.: 83055-99-6), flusulfuron-methyl (CAS No.: 145701-23-1), thifensulfuron-methyl (CAS No.: 79277-27-3), mesosulfuron-methyl (CAS No.: 208465-21-8), pyrazosulfuron-methyl (CAS No.: 422556-08-9), fluazolidone (CAS No.: 181274-17-9);

[0011] (5) ACCase inhibitors: quizalofop-p-ethyl (CAS No.: 113158-40-0), clodinafop-propargyl (CAS No.: 105512-06-9), and clodinafop-propargyl (CAS No.: 243973-20-8);

[0012] (6) PPO inhibitor: Bensulfuron-methyl (CAS No.: 372137-35-4) Trifluralin (CAS No.: 1258836-72-4);

[0013] (7) PSⅡ inhibitors: metribuzin (CAS No.: 21087-64-9), azoxystrobin (CAS No.: 129909-90-6), chlorpyrifos (CAS No.: 15545-48-9), isoproturon (CAS No.: 34123-59-6), octanoyl bromoxynil (CAS No.: 1689-99-2);

[0014] (8) Micro-assembly inhibitor: Pendimethalin (CAS No.: 40487-42-1);

[0015] (9) Synthetic hormone inhibitors: clopyralid (CAS No.: 69377-81-7), clopyralid isooctyl ester (CAS No.: 81406-37-3), 2-methyl-4-chlorophenoxyacetic acid (CAS No.: 94-74-6), 2,4-methyl-4-chloroisooctyl ester (CAS No.: 26544-20-7), 2,4-dichlorophenoxyacetic acid (CAS No.: 94-75-7), dicamba (CAS No.: 1918-00-9), fluopyridine ester (CAS No.: 943831-98-9)

[0016] (10) VLCFA inhibitors: fluthiamethoxam (CAS No.: 142459-58-3), sulfonylpyrazosulfuron (CAS No.: 447399-55-5), metolachlor (CAS No.: 87392-12-9), acetochlor (CAS No.: 34256-82-1);

[0017] (11) Inhibitor of lipid synthesis (non-acetyl-CoA carboxylase): Benzyl sulfadiazine (CAS No.: 52888-80-9);

[0018] (12) EPSPS inhibitor: glyphosate (CAS No.: 1071-83-6);

[0019] (13) GS inhibitor: glufosinate (CAS No.: 77182-82-2);

[0020] (14) Other inhibitors: Cyclohexane (CAS No.: 87818-31-3);

[0021] The weight ratio of A to B in the herbicidal composition is 1:800-50:1, 1:600-20:1, 1:300-10:1, 1:200-8:1, 1:180-5:1, 1:150-2:1, 1:120-1:1, 1:100-1:2, 1:80-1:4, 1:60-1:5, 1:50-1:8, 1:30-1:10, or 1:20-1:15.

[0022] The mass percentage of A and B in the herbicidal composition is 1-95% of the total, preferably 10-80%.

[0023] The herbicidal composition also contains conventional adjuvants, including carriers and / or surfactants.

[0024] 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.

[0025] Surfactants can include emulsifiers, dispersants, or wetting agents, and can be ionic or nonionic. Examples that may be mentioned include salts of polyacrylic acid, lignin sulfonates, salts of phenol sulfonic acid or naphthalene sulfonic acid, polymers of ethylene oxide with aliphatic alcohols or with aliphatic acids or with aliphatic amines and substituted phenols (especially alkylphenols or arylphenols), sulfosuccinates, taurine derivatives (especially alkyl taurine esters), and phosphate esters of alcohols or polyhydroxyethylated phenols, alkyl sulfonates, alkyl aryl sulfonates, alkyl sulfates, lauryl ether sulfates, fatty alcohol sulfates, and sulfated hexadecyl, heptadecanols, and octadecyl alcohols, as well as sulfated fatty alcohol glycol ethers, and naphthalene or naphthalene sulfonic acid with phenol and formaldehyde. Condensations, polyoxyethylene octylphenyl ether, ethoxylated isooctylphenol, octylphenol or nonylphenol, alkylphenyl polyethylene glycol ether, tributylphenyl polyethylene glycol ether, tripearylphenyl polyethylene glycol ether, alkylaryl polyether alcohol, alcohols and fatty alcohols / ethylene oxide condensates, ethoxylated castor oil, polyoxyethylene alkyl ether, ethoxylated polyoxypropylene, lauryl polyethylene glycol ether acetal, sorbitan ester, lignin sulfite waste liquid, and proteins, denatured proteins, polysaccharides (e.g., methylcellulose), hydrophobically modified starch, polyvinyl alcohol, polycarboxylates, polyalkoxylated compounds, polyethyleneamine, polyvinylpyrrolidone and copolymers thereof. At least one surfactant is required to facilitate the dispersion of the active ingredients in water and to facilitate their proper application to plants.

[0026] The above composition may also contain various other components, such as protective colloids, adhesives, thickeners, thixotropic agents, penetrants, stabilizers, chelating agents, dyes, colorants, and polymers.

[0027] 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, DOWCO535, DK-8910, V-53482, PP-600, MBH-001, KIH-9201, ET-751, KIH-6127 and KIH-2023. ,

[0028] The herbicidal composition further includes at least one safener selected from:

[0029] a) Dichlorophenylpyrazoline-3-carboxylic acid (S1) compounds, preferably ethyl 1-(2,4-dichlorophenyl)-5-(ethoxycarbonyl)-5-methyl-2-pyrazoline-3-carboxylic acid (S1-1, mefenpyr-diethyl, PM, pp. 594-595), and related compounds described, for example, in WO91 / 07874 and PM (pp. 594-595).

[0030] b) Dichlorophenylpyrazole carboxylic acid derivatives, preferably compounds such as 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.

[0031] c) Triazole carboxylic acid (S1) compounds, preferably 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).

[0032] d) 5-Benzyl- or 5-phenyl-2-isoxazoline-3-carboxylic acid or 5,5-diphenyl-2-isoxazoline-3-carboxylic acid compounds, preferably ethyl 5-(2,4-dichlorobenzyl)-2-isoxazoline-3-carboxylic acid (S1-7) or ethyl 5-phenyl-2-isoxazoline-3-carboxylic acid (S1-8) and related compounds described in WO91 / 08202, or ethyl 5,5-diphenyl-2-isoxazoline-3-carboxylic acid (S1-9, isoxadifen-ethyl) or n-propyl 5,5-diphenyl-2-isoxazoline-3-carboxylic acid (S1-10) or ethyl 5-(4-fluorophenyl)-5-phenyl-2-isoxazoline-3-carboxylic acid (S1-11) described in patent application (WO-A-95 / 07897).

[0033] e) 8-quinolinoxyacetic acid (S2) compounds, preferably 1-methylhexyl-1-yl(5-chloro-8-quinolinoxy)acetate (S2-1, cloquintocet-mexyl, such as PM (pages 195-196), (1,3-dimethylbut-1-yl)(5-chloro-8-quinolinoxy)acetate (S2-2), 4-allyloxybutyl(5-chloro-8-quinolinoxy)acetate (S2-3), 1-allyloxypropyl-2-yl(5-chloro-8-quinolinoxy)acetate (S2-4), (5-chloro- Ethyl 8-quinolinoxy)acetate (S2-5), methyl (5-chloro-8-quinolinoxy)acetate (S2-6), allyl (5-chloro-8-quinolinoxy)acetate (S2-7), 2-(2-propyliminooxy)-1-ethyl(5-chloro-8-quinolinoxy)acetate (S2-8), 2-oxopropyl-1-yl(5-chloro-8-quinolinoxy)acetate (S2-9), and related compounds described in EP-A-86750, EP-A-94349 and EP-A-191736 or EP-A-0492366.

[0034] f) (5-chloro-8-quinolinoxy)malonic acid compounds, preferably, for example, diethyl (5-chloro-8-quinolinoxy)malonate, diallyl (5-chloro-8-quinolinoxy)malonate, methyl ethyl (5-chloro-8-quinolinoxy)malonate and related compounds described in EP-A-0582198.

[0035] g) Phenoxyacetic acid, phenoxypropionic acid or aromatic carboxylic acid active compounds, such as 2,4-dichlorophenoxyacetic acid (and ester) (2,4-D), 4-chloro-2-methylphenoxypropionate (2-methyl-4-chloropropionic acid (mecoprop)), MCPA or 3,6-dichloro-2-methoxybenzoic acid (and ester) (dicamba)

[0036] h) Pyrimidine active compounds, such as fenclorim (PM, pp. 386-387) (=4,6-dichloro-2-phenylpyrimidine),

[0037] i) Dichloroacetamide-type active compounds, commonly used as pre-emergence safeners (safeners acting on the soil), such as "dichloroacetamide" (PM, pages 270-271) (=N,N-diallyl-2,2-dichloroacetamide), "AR-29148" (=3-dichloroacetyl-2,2,5-trimethyl-1,3-oxazolidinone, purchased from Stauffer), "benoxacor" (PM, pages 74-75) (=4-dichloroacetyl-3,4-dihydro-3-methyl-2H-1,4-benzoxazine), "APPG-1292" (=N-allyl-N[(1,3-dioxolane-2-yl)-methyl]dichloroacetamide, purchased from PPGindustries), and "ADK-24". (=N-allyl-N-[(allylaminocarbonyl)-methyl]-dichloroacetamide, purchased from Sagro-Chem), “AAD-67” or “AMON4660” (=3-dichloroacetyl-1-oxa-3-aza-spiro[4,5]decane, purchased from Nitrokemia or Monsanto), “diclonon” or “ABAS145138” or “ALAB145138” (=(=3-dichloroacetyl-2,5,5-trimethyl-1,3-diazabicyclo[4.3.0]nonane, purchased from BASF), and “furilazol” or “AMON13900” (see PM, 482-483) (=(RS)-3-dichloroacetyl-5-(2-furanyl)-2,2-dimethyloxazolidinone),

[0038] j) Dichloroacetone derivatives, such as "AMG191" (CAS Registry No. 96420-72-3) (=2-dichloromethyl-2-methyl-1,3-dioxolane, purchased from Nitrokemia).

[0039] 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.

[0040] 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.

[0041] 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.

[0042] 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.

[0043] 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).

[0044] 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).

[0045] 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.

[0046] In the context of this invention, the salt of the compound is preferably an alkali metal salt (such as lithium, sodium, and potassium salts), an alkaline earth metal salt (such as calcium and magnesium salts), a transition metal salt (such as manganese, copper, zinc, and iron salts), an ammonium salt, or a substituted ammonium salt in which 1-4 hydrogen atoms are replaced by C1-C4 alkyl, hydroxy-C1-C4 alkyl, C1-C4 alkoxy-C1-C4 alkyl, hydroxy-C1-C4 alkoxy-C1-C4 alkyl, phenyl, or benzyl groups, preferably ammonium, methylammonium, isopropylammonium, dimethylammonium, diisopropylammonium, trimethylammonium, heptylammonium, dodecylammonium, tetradecylammonium, tetramethylammonium, tetraethylammonium, tetrabutylammonium, or 2-hydroxyammonium. Ethylammonium (alcoholic acid salt), 2-(2-hydroxyeth-1-oxy)eth-1-ylammonium (diethylene glycolamine salt), di(2-hydroxyeth-1-yl)ammonium (diethylene glycolamine salt), tri(2-hydroxyethyl)ammonium (triethanolamine salt), tri(2-hydroxypropyl)ammonium, benzyltrimethylammonium, benzyltriethylammonium, N,N,N-trimethylethanolammonium (choline salt), and also phosphonium ions, sulfonium ions, preferably tri(C1-C4 alkyl)sulfonium, such as trimethylsulfonium, and sulfonium oxide ions, preferably tri(C1-C4 alkyl)sulfonium oxide, and finally, in the form of salts of polyamines such as N,N-di(3-aminopropyl)methylamine and diethylenetriamine.

[0047] In the context of this invention, the ester of the compound, for example as an alkyl ester, alkenyl ester, alkynyl ester, alkoxyalkyl ester, tetrahydrofuranylmethyl ester, and the corresponding thioester, is preferably C1-C. 10 Alkyl esters, C2-C 10 alkenyl ester, C2-C 10 alkynyl esters, C1-C 10 Alkoxy C1-C 10 Alkyl esters, (tetrahydrofuran-2-yl)methyl esters, and corresponding thioesters. Preferred C1-C 10 Alkyl esters or C1-C 10 Alkyl thioesters are, for example, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, pentyl, methylhexyl (1-methylhexyl), methylheptyl (1-methylheptyl), heptayl, octyl, or isooctyl (2-ethylhexyl) esters. Preferred C1-C... 10 Alkoxy-C1-C 10 Alkyl esters are C1-C4 alkoxyethyl esters, such as 2-methoxyethyl, 2-ethoxyethyl, 2-butoxyethyl (butoxyethyl), 2-butoxypropyl, or 3-butoxypropyl esters.

[0048] The compositions of the present invention can be diluted or used directly by the user before use. They can be prepared by conventional processing methods, namely, mixing the active substance with a liquid solvent or solid carrier, and then adding one or more surfactants such as dispersants, stabilizers, wetting agents, binders, and defoamers.

[0049] The specific formulations of the herbicidal composition are dispersible oil suspensions, aqueous suspensions, emulsions, wettable powders, emulsifiable concentrates, water-dispersible granules (dry suspensions), water emulsions, and microemulsions.

[0050] In short, the compositions of the present invention can be mixed with solid and liquid additives conventionally used in prior art formulations. The amount of active ingredient used varies with changing external conditions, such as temperature, humidity, and the nature of the herbicide used. It can vary considerably, for example, from 0.001 to 2.0 kg / ha, or more active substances, but is preferably between 0.003 and 1.0 kg / ha, particularly between 5 and 500 g / ha.

[0051] The present invention also provides an application of the herbicidal composition in controlling weeds; and a method for controlling unwanted plant growth, comprising applying the herbicidal composition to a plant, plant part, plant seed or area where the plant is growing.

[0052] In addition, the composition of the present invention can be applied to the leaves of the plant to be treated by spraying, i.e., applied to weeds, especially to surfaces that are infested or susceptible to weed infestation.

[0053] When the herbicidal compositions of the present invention are applied, unexpected synergistic effects are achieved, and the herbicidal activity is significantly greater than the expected sum of the activities of using a single herbicide, as well as the activity of a single herbicide. The synergistic effects manifest as reduced application rates, a broader spectrum of weed control, faster and more sustained weed control—characteristics needed in weed control practices. In terms of the described properties, these new compositions are significantly superior to existing herbicides, achieving reduced application rates and being more environmentally friendly.

[0054] The synergistic herbicidal composition of the present invention also has the following advantages:

[0055] (1) The compositions of the present invention are environmentally friendly and are easily degraded in the environment.

[0056] (2) The herbicide composition of the present invention is low in cost and easy to use, and its promotion and application have great economic and social benefits. Detailed Implementation

[0057] The following examples are not intended to limit the invention, but are merely illustrative of how the invention is implemented. These examples demonstrate particularly significant effectiveness against certain weeds. Examples are as follows:

[0058] A) Example

[0059] 1. A+ Bisoxane (1+5) EC

[0060] 1% A + 5% Bismuth subtilis + 20% DMAC + 3% Calcium dodecylbenzenesulfonate + 8% Phenethylphenol polyoxyethylene ether + 180# solvent oil to make up the difference

[0061] 2. A+ Cyclopyralid (1+22.5) Dispersible Oil Suspension

[0062] 1% A + 22.5% Cyclopyralid + 5% Calcium Dodecylbenzenesulfonate + 10% Cashew Phenolic Ethylene Ether + 3% Castor Oil Ethylene Ether + 1.0% Organo-Bentonite + 5% 180# Solvent Oil + 20% Soybean Oil + Methyl Oleate (to make up the difference)

[0063] 3. A+pyrfluthrin (1+25) aqueous suspension

[0064] 1% A + 25% pyrfluthrin + 3% phenethylphenol polyoxyethylene ether phosphate triethanolamine salt + 1.5% propylene glycol block polyether + 2% fatty alcohol polyoxyethylene ether + 0.14% xanthan gum + 1.8% magnesium aluminum silicate + 4% glycerol + defoamer + water

[0065] 4. A+Beflubutamid-M(1+25) emulsifiable concentrate

[0066] 1% A + 25% Beflubutamid-M + 8% DMAC + 4% Calcium Dodecylbenzenesulfonate + 5% Phenethylphenol Polyoxyethylene Ether + 180# Solvent Oil (to make up the difference)

[0067] 5. A+ (1+50) wettable powder

[0068] 1%A+50% +10% silica + 2% sodium dodecylbenzenesulfonate + 4% naphthalenesulfonate dispersant + diatomaceous earth (to make up the difference)

[0069] 6. A+ dichloroisoxane (1+50) aqueous suspension

[0070] 1% A + 50% dichloroisoxane + 3% phenethylphenol polyoxyethylene ether phosphate triethanolamine salt + 1.5% polycarboxylate salt + 1% fatty alcohol polyoxyethylene ether + 0.06% xanthan gum + 4% glycerol + defoamer + water

[0071] 7. A+ Biflusulfonamide (2+2.5) Dispersible Oil Suspension

[0072] 2% A + 2.5% diflubenzuron + 5% calcium dodecylbenzenesulfonate + 8% fatty acid polyoxyethylene ester + 5% castor oil polyoxyethylene ether + 2.5% organobentonite + 3% fumed silica + 5% 180# solvent oil + soybean oil to make up the difference.

[0073] 8. A+ Pyrazosulfuron (1+2.5) dispersible oil suspension

[0074] 1% A + 2.5% pyrazosulfan (1+2.5) + 5% calcium dodecylbenzenesulfonate + 9% fatty acid polyoxyethylene ester + 6% castor oil polyoxyethylene ether + 3% organo-bentonite + 3% fumed silica + 5% 180# solvent oil + soybean oil to make up the difference.

[0075] 9. A+ Mesosulfuron-methyl (1+2.5) Dispersible Oil Suspension

[0076] 1% A + 2.5% Methyl disulfuron + 1% Stabilizer + 5% Calcium dodecylbenzenesulfonate + 9% Fatty acid polyoxyethylene ester + 6% Castor oil polyoxyethylene ether + 3% Organo-bentonite + 3% Fumed silica + 5% 180# solvent oil + 5% Mixed fatty acid methyl ester + Soybean oil to make up the difference

[0077] 10. A+ cyclohexane (1+12.5) emulsifiable concentrate

[0078] 1% A + 12.5% ​​cyclohexane + 8% DMAC + 8% calcium dodecylbenzenesulfonate + 15% cashew phenol polyoxyethylene ether + 5% triphenyl phosphate + 180# solvent oil to make up the difference.

[0079] 11.A+Octayl bromoxynil (1+30) emulsifiable concentrate

[0080] 1% A + 30% octanoyl bromide nitrile (1+30) + 5% DMAC + 4% calcium dodecylbenzenesulfonate + 6% cashew phenol polyoxyethylene ether + 200# solvent oil to make up the difference

[0081] 12.A+Clonopyroxyacetate isooctyl ester (1+15) emulsifiable concentrate

[0082] 1% A + 15% clopyralid isooctyl ester + 5% DMAC + 8% calcium dodecylbenzenesulfonate + 10% dodecylphenol polyoxyethylene ether + 200# solvent oil to make up the difference.

[0083] 13.A+2-methyl-4-chloroisooctyl ester (1+50) emulsifiable concentrate

[0084] 1% A + 50% 2,4-methyl-4-chloroisooctyl ester + 5% DMAC + 4% calcium dodecylbenzenesulfonate + 5% cashew phenol polyoxyethylene ether + 180# solvent oil to make up the difference

[0085] 14. emulsifiable concentrate

[0086] 1%A+5% +5% DMAC +6% Calcium Dodecylbenzenesulfonate +10% Cashew Phenolic Ether +10% 180# Solvent Oil + Methyl Oleate (to make up the difference)

[0087] 15. A+ Fluorochloropyridine ester (2+1.5) dispersible oil suspension

[0088] 2% A + 1.5% fluorochloropyridine ester + 5% calcium dodecylbenzenesulfonate + 10% fatty acid polyoxyethylene ester + 6% castor oil polyoxyethylene ether + 3% organobentonite + 3% fumed silica + 5% 180# solvent oil + 5% n-butyl oleate + soybean oil to make up the difference.

[0089] The processing equipment for the above emulsifiable oil includes: a vacuum pump, a batching vessel, and a storage tank.

[0090] The above-mentioned emulsifiable oil processing procedure is as follows: all materials are put into the mixing tank, stirred and dissolved until completely transparent, and after passing the test, they are transferred to the storage tank for filling.

[0091] The above-mentioned wettable powder processing equipment includes: mechanical pulverizer and air jet mill.

[0092] The above-mentioned wettable powder processing procedure is as follows: all materials, including the active ingredient and additives, are put into a mechanical pulverizer, then passed through an airflow pulverizer, and after sampling and testing, they are ready for use.

[0093] The above-mentioned water suspension processing equipment includes: mixing tank, colloid mill, sand mill, shearing machine, etc.

[0094] The above-mentioned water suspension processing procedure is as follows: all materials are put into a mixing tank, stirred and mixed, then passed through a colloid mill, then entered a three-stage sand mill, and finally sheared evenly in a shearing machine. After passing the test, the materials are transferred to a storage tank for filling.

[0095] The above-mentioned equipment for processing dispersible oil suspensions includes: mixing tank, colloid mill, sand mill, shearing machine, etc.

[0096] The above-mentioned dispersible oil suspension processing procedure is as follows: all materials are put into a mixing tank, stirred and mixed, then passed through a colloid mill, then entered a sand mill for three-stage sand milling, and finally sheared evenly in a shearing machine. After passing the test, the mixture is transferred to a storage tank for filling.

[0097] B) Pharmacological efficacy test

[0098] Post-emergence foliar spraying:

[0099] 1) Test conditions

[0100] 1.1) Test Target

[0101] Weeds were cultivated using a pot method, with 180x140mm plastic seedling pots placed in enamel trays. The pots were filled with topsoil (4 / 5 full) collected from farmland, dried and sieved. The soil moisture was initially controlled at 20%. Weed seeds with plump and uniform grains were selected, soaked in 25℃ warm water for 6 hours, and germinated in a 28℃ biochemical incubator (in darkness). The newly sprouted weed seeds were then evenly placed on the soil surface and covered with 0.5-1cm of soil, depending on the seed size.

[0102] 1.2) Cultivation conditions

[0103] The experiment was conducted in a controlled greenhouse at a temperature of 20–30°C, under natural light, and with a relative humidity of 55%–75%. The soil type was loam, with an organic matter content of 1.63%, pH = 7.1, available nitrogen of 84.3 mg / kg, available phosphorus of 38.5 mg / kg, and available potassium of 82.1 mg / kg.

[0104] 1.3) Instruments and Equipment

[0105] 3WP-2000 mobile spray tower, Nanjing Agricultural Machinery Research Institute, Ministry of Agriculture; GA10 0.01% electronic balance (Germany); ZDR2000 intelligent data logger (Hangzhou Zeda Instrument Co., Ltd.); SPX intelligent biochemical incubator (Ningbo Jiangnan Instrument Factory).

[0106] 2) Experimental Design

[0107] 2.1) Reagents

[0108] The required active ingredient A was prepared according to the method described in patent CN108586357A, and the required active ingredient B was purchased from a reagent company or prepared using known methods. All raw materials were prepared using acetone as a solvent and diluted with a 0.1% Tween-80 emulsifier aqueous solution, diluted immediately before use.

[0109] 2.2) Test Treatment

[0110] 2.2.1) Dosage setting

[0111] When determining the ratio or content of active ingredient A and active ingredient B, the characteristics of the two agents and their toxicity should be considered, as well as the main purpose of the formulation. Based on preliminary tests, this study sets the dosages of active ingredients A and B, used alone and in combination, as shown in the table. Water containing the same solvent and emulsifier but without any agents was used as a blank control.

[0112] 2.2.2) Experimental repetition

[0113] Each treatment was repeated 4 times, with 3 pots per treatment. Each pot was sown with 20 weed seeds, resulting in a total of 60 plants per treatment.

[0114] 2.3) Processing method

[0115] 2.3.1) Processing time and number of times

[0116] The experiment used the same pesticide once. When the weeds reached the 1-1.5 leaf stage, the seedlings were thinned to keep 10 weeds per pot, and 30 weeds were retained for each treatment. The plants were then cultivated until they reached the 2.5-4.5 leaf stage before further treatment.

[0117] 2.3.2) Use of instruments and methods of medication

[0118] The cultured test material was evenly placed on a 0.5m² area. 2 On the platform, use a 3WP-2000 mobile spray tower for foliar spraying, with a spray volume of 450 kg / ha and a spray pressure of 0.3 MPa. After all the pesticide solution has been sprayed, close the air valve. After 30 seconds, open the spray tower door and remove the nutrient pots. Then open the air valve and spray 50 mL of clean water to clean the spray pipes.

[0119] 3) Test methods

[0120] Pot cultivation was used. Weed cultivation is described in section 1.1), following the guidelines for indoor bioassays of pesticides (herbicides). Application methods are described in section 2.3.2), using the foliar treatment method. After treatment, the plants were transferred to a greenhouse for conventional cultivation.

[0121] 4) Data survey and statistical analysis

[0122] 4.1) Survey Methods

[0123] The absolute number method was used. Surviving weed seedlings were cut along the soil surface with a blade, and their fresh weight was measured using an analytical balance. Dead weeds were counted as having a fresh weight of zero.

[0124] 4.2) Survey time and frequency

[0125] An investigation was conducted 21 days after the incident, for a total of one investigation.

[0126] 4.3) Data Statistical Analysis

[0127] The theoretical fresh weight inhibition rate (E0 = X + Y) of each treatment combination was calculated using the Gowing method. This was then compared with the measured inhibition rate (E) to evaluate the combined effect of the two treatments on weeds. An E-E0 value greater than 10% indicates a synergistic effect, less than -10% indicates an antagonistic effect, and between -10% and 10% indicates an additive effect. The optimal ratio was determined based on actual efficacy, herbicide characteristics, and formulation balance. In the formula, X represents the fresh weight inhibition rate when active ingredient A is at dosage P; Y represents the fresh weight inhibition rate when active ingredient B is at dosage Q.

[0128] Soil sealing treatment:

[0129] 1) Test conditions

[0130] 1.1) Cultivation conditions

[0131] The process is carried out in a controlled greenhouse with a temperature of 20–30°C, natural light, and a relative humidity of 55%–75%.

[0132] The soil type was loam, with an organic matter content of 1.63%, pH = 7.1, available nitrogen 84.3 mg / kg, available phosphorus 38.5 mg / kg, and available potassium 82.1 mg / kg. The soil was quantitatively filled to 3 / 4 full in pots, and then watered from the bottom to completely saturate the soil. The tested weed seeds were pre-germinated until they showed signs of germination, then evenly and quantitatively sown on the surface, covered with 0.5-1 cm of soil depending on seed size, and left to germinate for 72 hours.

[0133] 1.2) Instruments and Equipment

[0134] GA10 type electronic balance with a strength of 0.01% (Germany); ZDR2000 intelligent data logger (Hangzhou Zeda Instrument Co., Ltd.); SPX type intelligent biochemical incubator (Ningbo Jiangnan Instrument Factory), pipettes, etc.

[0135] 2) Experimental Design

[0136] 2.1) Reagents

[0137] 2.1.1) Test reagents

[0138] The original drug uses acetone as a solvent and is diluted with an aqueous solution of 0.1% emulsifier T-80. It is diluted immediately before use.

[0139] 2.2) Test Treatment

[0140] 2.2.1) Dosage setting

[0141] When determining the distribution ratio or content of active ingredient A and active ingredient B in each group, the characteristics of action and toxicity of the two agents should be considered, as well as the main purpose of the formulation. Based on preliminary tests, this study sets the dosages of active ingredients A and B, both individually and in combination, as shown in the table. Water containing the same solvent and emulsifier but without any agents was used as a blank control.

[0142] 2.2.2) Experimental repetition

[0143] Each treatment was repeated 4 times, with 3 pots per treatment per session, and 30 weed seeds sown in each pot.

[0144] 2) Test methods

[0145] Before treatment, irrigate to maintain a 1-2 cm water layer. Use a pipette to take a quantitative amount of drug solution and irrigate according to the experimental design, from low dose to high dose, with each treatment repeated 4 times. After treatment, transfer to a greenhouse for routine cultivation, maintaining a 1-2 cm water layer throughout the experiment.

[0146] 3) Data survey and statistical analysis

[0147] The treatment is the same as post-emergence foliar spraying, so it will not be described in detail again.

[0148] The statistical results are shown in Table 1-43 below. Except for those clearly marked "soil treatment", all others are "post-emergence foliar spray treatment".

[0149] Table 1A Evaluation of the actual control efficacy and combined effects of the combination of bixamethasone and cyclohexane against *Hedyotis diffusa*.

[0150]

[0151] Table 2A Evaluation of the actual control efficacy and combined effects of the mixed cyclopyridoxine against *Hedyotis diffusa*.

[0152]

[0153] Table 3A Evaluation of the actual control efficacy and combined effects of the combination of pyrifluquinazon and cyclophosphamide against wild rapeseed.

[0154]

[0155] Table 4A Evaluation of the actual control efficacy and combined effects of flupyridine and fluopyram on wild rapeseed.

[0156]

[0157]

[0158] Table 5A Evaluation of the actual control efficacy and combined effects of the Beflubutamid-M mixture against wild rapeseed.

[0159]

[0160] Table 6A Evaluation of the actual control efficacy and combined effects of the combination of dichloroisoxane and cyclohexane against barnyardgrass.

[0161]

[0162] Table 7A Mixtures Evaluation of actual control efficacy and combined effects against barnyard grass

[0163]

[0164] Table 8A Evaluation of the actual control efficacy and combined effects of bensulfuron-methyl against *Desmodium styracifolium*

[0165]

[0166] Table 9A Evaluation of the actual control efficacy and combined effects of the combination of bensulfuron-methyl and pyrimethanil against *Desmodium styracifolium*.

[0167]

[0168]

[0169] Table 10A Evaluation of the actual control efficacy and combined effects of the combination of diflubenzuron and diflubenzuron against shepherd's purse.

[0170]

[0171] Table 11A Evaluation of the actual control efficacy and combined effects of the combination of thifensulfuron-methyl against *Desmodium styracifolium*.

[0172]

[0173] Table 12A Evaluation of the actual control efficacy and combined effects of the combination of mesosulfuron-methyl against *Desmodium styracifolium*.

[0174]

[0175] Table 13A Evaluation of the actual control efficacy and combined effects of the mixed compound of acesulfame K and chlorpyrifos against shepherd's purse.

[0176]

[0177] Table 14A Evaluation of the actual control efficacy and combined effects of the combination of fluazofur and flufenoxuron against *Desmodium styracifolium*.

[0178]

[0179] Table 15A Evaluation of the actual control efficacy and combined effects of the combination of quizalofop-p-ethyl and clopyralid against barnyardgrass.

[0180]

[0181]

[0182] Table 16A Evaluation of the actual control efficacy and combined effects of the combination of clodinafop-propargyl and clodinafop-propargyl against barnyardgrass.

[0183]

[0184] Table 17A Evaluation of the actual control efficacy and combined effects of the combination of oxychlorpyrifos and clopyralid against purslane.

[0185]

[0186] Table 18A Evaluation of the actual control efficacy and combined effects of the mixture of bensulfuron-methyl and pyrimethanil against cleavers.

[0187]

[0188] Table 19A Mixtures Evaluation of the actual control efficacy and combined effects of cleavers

[0189]

[0190] Table 20A Mixtures Evaluation of the actual control efficacy and combined effects of cleavers

[0191]

[0192] Table 21A Evaluation of the actual control efficacy and combined effects of trifluralin and trifluralin against cleavers

[0193]

[0194] Table 22A Evaluation of the actual control efficacy and combined effects of the mixed metribuzin against *Gnaphalium affine*.

[0195]

[0196] Table 23A Evaluation of the actual control efficacy and combined effects of the mixture of aminopyrazosulfuron and acetamiprid against *Gnaphalium affine*.

[0197]

[0198] Table 24A Evaluation of the actual control efficacy and combined effects of the mixture of green meropenem and chloromethrin against megazos.

[0199]

[0200] Table 25A Evaluation of the Actual Control Efficacy and Combined Effect of Isoproturon-Based Combination on Megaspermum erythrorhizon

[0201]

[0202] Table 26A Evaluation of the actual control efficacy and combined effects of the mixture of octanoyl bromoxynil against *Megalophyllum hepatica*.

[0203]

[0204] Table 27A Evaluation of the actual control efficacy and combined effects of pendimethalin and other compound formulations against duckweed (soil treatment)

[0205]

[0206] Table 28A Evaluation of the actual control efficacy and combined effects of clopyralid against chickweed.

[0207]

[0208] Table 29A Evaluation of the actual efficacy and combined effects of the combination of clopyralid isooctyl ester and chickweed.

[0209]

[0210] Table 30A Evaluation of the actual control efficacy and combined effects of 2-methyl-4-chlorophenoxyacetic acid on chickweed.

[0211]

[0212]

[0213] Table 31A Evaluation of the actual control efficacy and combined effects of the combination of 2,4-methyl-4-chloroisooctyl ester against Stellaria media.

[0214]

[0215] Table 32A Evaluation of the actual control efficacy and combined effects of 2,4-dichlorophenoxyacetic acid on chickweed.

[0216]

[0217] Table 33A Evaluation of the actual control efficacy and combined effects of dicamba and its combination with chickweed on chickweed.

[0218]

[0219] Table 34A Evaluation of the actual efficacy and combined effects of the combination of fluopyridine ester and fluorochloropyridine ester against Stellaria media.

[0220]

[0221] Table 35A Mixture Evaluation of the actual control efficacy and combined effects of chickweed

[0222]

[0223]

[0224] Table 36A Evaluation of the actual control efficacy and combined effects of the mixed fluthiamethoxam against barnyardgrass (soil treatment)

[0225]

[0226] Table 37A Evaluation of the actual control efficacy and combined effects of the mixed sulfonium pyrazole against barnyardgrass (soil treatment)

[0227]

[0228] Table 38A Evaluation of the actual control efficacy and combined effects of the mixture of metolachlor and succinate against barnyardgrass (soil treatment)

[0229]

[0230] Table 39A Evaluation of the actual control efficacy and combined effects of acetochlor mixture against barnyardgrass (soil treatment)

[0231]

[0232] Table 40A Evaluation of the actual control efficacy and combined effects of the mixed herbicide bensulfuron-methyl against barnyardgrass.

[0233]

[0234]

[0235] Table 41A Evaluation of the actual control efficacy and combined effects of glyphosate-mixed formulation against *Tamarix chinensis*

[0236]

[0237] Table 42A Evaluation of the actual control efficacy and combined effects of glufosinate-ammonium against Erigeron simonii.

[0238]

[0239] Table 43A Evaluation of the actual control efficacy and combined effects of the combination of cyclohexane and cyclohexane against *Gnaphalium affine* (soil treatment)

[0240]

[0241] C) Field Demonstration

[0242] The efficacy of the herbicidal compositions prepared in Examples 1-15 above against the weed Veronica persica was tested.

[0243] Post-emergence foliar spraying: Manually spray when the weeds have grown to 2.5-4.5 leaves, using a diluted solution of 45 kg / 667 m². 2 Spray the stems and leaves evenly.

[0244] The specific experimental agents and dosages are detailed in Table 44. The plot area was 20 square meters, and each treatment was repeated three times. The control effect was investigated 30 days after application and is shown in Table 44.

[0245]

[0246] Table 44 shows the field demonstration effects of the compound compositions described in the table.

[0247]

[0248]

[0249] Through extensive experimentation and exploration, this invention unexpectedly discovered that the composition exhibits a surprising and unexpected synergistic effect in controlling weeds such as *Gnaphalium affine*, wild rapeseed, barnyard grass, *Desmodium styracifolium*, *Gnaphalium affine*, *Gnaphalium affine*, *Gnaphalium affine*, *Monochoria vaginalis*, *Stellaria media*, *Digitaria sanguinalis*, *Fructus urinaria*, *Erigeron canadensis*, and *Veronica persica*. This synergistic effect is more pronounced at low doses, reducing the amount of herbicide used and environmental pollution. Furthermore, rational formulation lowers agricultural costs, demonstrating excellent application prospects. Simultaneously, tests have shown good selectivity and excellent synergistic effects in wheat fields, corn fields, rice fields, peanut fields, sugarcane fields, sorghum fields, millet fields, potato fields, rapeseed fields, soybean fields, cotton fields, vegetables, *Poa annua*, tall fescue fields, and *Zoysia japonica* fields, indicating its potential for development into a herbicide mixture with broad market value.

Claims

1. A herbicidal composition comprising a pyrimidyl formhydroxamyl derivative, characterized in that, comprising a herbicidally effective amount of active ingredient A and active ingredient B, wherein Active ingredient A is ; active ingredient B is selected from one of the following compounds: (1) HPPD inhibitors: Pyrazolynate, Pyrasulfotole; (2) PDS inhibitors: Flupyr-aminophos, Pyraziflumid, Beflubutamid-M; (3) DOXP inhibitors: dichloroisonixoxime, (4) EPSP synthase inhibitors: glyphosate, glufosinate-ammonium, bilanafos, phosphinothricin, ; (4) ALS inhibitors: Benzosulfuron-methyl, Bensulfuron-methyl, Fluridone, Thifensulfuron-methyl, Mesosulfuron-methyl, Pyroxasulfone, Flucarbazone-sodium; (5) ACCase inhibitors: Fenoxaprop-P-ethyl, Cloproxydim, Pinoxaden; (6) PPO inhibitors: pyrimisulfuron, , Trifluralin; (7) PS II inhibitors: Metribuzin, Amicarbazone, Chlorotoluron, Isoproturon, Cloquintocet-mexyl; (8) Microtubule assembly inhibitors: Pendimethalin; (9) Synthetic hormone inhibitors: clopyralid, clopyralid isooctyl ester, 2-methyl-4-chlorophenoxyacetic acid, 2,4-methyl-4-chloroisooctyl ester, 2,4-dichlorophenoxyacetic acid, dicamba, fluchloropyridine ester, ; (10) VLCFA inhibitors: Flufenacet, Buthidazole, S-metolachlor, Acetochlor; (11) Lipid synthesis inhibitors: Propanil; (12) EPSPS inhibitors: Glyphosate; (13) GS inhibitors: Glufosinate-ammonium; (14) Other inhibitors: Cinmethylin; When B is bispyribac-methyl, flupyrazole, bensulfuron-methyl, or pyrimisulfuron-methyl, , When using cyprodinil or cyclohexane, the weight ratio of A to B in the herbicidal composition is 1:10 to 8:5; when B is Pyrasulfotole, the weight ratio of A, B in the herbicidal composition is 1:30~8:15; when B is pyraflufen-ethyl, Beflubutamid-M, flurtamone, or metalaxyl-M, the weight ratio of A, B in the herbicidal composition is 1:20~4:5; when B is Amicarbazone, the weight ratio of A, B in the herbicidal composition is 1:40~2:5; when B is when B is pendimethalin, s- metamifop, acetochlor or glyphosate, the weight ratio of A, B in the herbicidal composition is 1:100-4:25; when B is Benzosulfuron-methyl, Mesosulfuron-methyl, Pyroxasulfone or Fluazapyr, the weight ratio of A, B in the herbicidal composition is 1:2~8:1; when B is Fluridone, the weight ratio of A, B in the herbicidal composition is 1:1~16:1; when B is Thifensulfuron-methyl, the weight ratio of A, B in the herbicidal composition is 1:4~4:1; when B is Fluazasulfuron, the weight ratio of A, B in the herbicidal composition is 1:6~8:3; when B is Fenoxaprop-P-ethyl, Cloproxydim, Pinoxaden or Cloquintocet-mexyl, the weight ratio of A, B in the herbicidal composition is 1:15~4:5; when B is Chlorotoluron or Isoproturon, the weight ratio of A, B in the herbicidal composition is 1:150~2:25; when B is Fluroxypyr, the weight ratio of A, B in the herbicidal composition is 1:30~4:5; when B is Fluroxypyr-isooctyl, the weight ratio of A, B in the herbicidal composition is 1:50~8:25; when B is 2-methyl-4-chlorophenoxyacetic acid, the weight ratio of A, B in the herbicidal composition is 1:75~16:75; when B is 2-methyl-4-chlorophenoxyacetic acid-isooctyl, the weight ratio of A, B in the herbicidal composition is 1:125~1:25; when B is 2,4-dichlorophenoxyacetic acid, the weight ratio of A, B in the herbicidal composition is 1:150~8:75; when B is Dicamba, the weight ratio of A, B in the herbicidal composition is 1:75~4:25; when B is Propanil, the weight ratio of A, B in the herbicidal composition is 1:600~2:75; when B is Glufosinate-ammonium, the weight ratio of A, B in the herbicidal composition is 1:80~4:

25.

2. The herbicidal composition according to claim 1, wherein, When B is bispyribac-methyl, flupyrazole, bensulfuron-methyl, or pyrimisulfuron-methyl, , When using cyprodinil or cyclohexane, the weight ratio of A to B in the herbicidal composition is 1:10 to 1:1; when B is picolinafen, the weight ratio of A to B in the herbicidal composition is 1:30 to 1:2; when B is pyraflufen-ethyl, Beflubutamid-M, flurtamone, or metalaxyl-M, the weight ratio of A, B in the herbicidal composition is 1:20~1:2; when B is dichloroisonixin, amicarbazone or fluorotolan, the weight ratio of A to B in the herbicidal composition is 1:30 to 1:4; when B is when B is pendimethalin, s- metamifop, acetochlor or glyphosate, the weight ratio of A, B in the herbicidal composition is 1: 100-1:8; when B is benzenesulfonuron, mesosulfuron, pyroxasulfone or flurotyl, the weight ratio of A to B in the herbicidal composition is 1:2 to 5:1; when B is fluthiacet-methyl, the weight ratio of A to B in the herbicidal composition is 1:1 to 10:1; when B is thifensulfuron-methyl, the weight ratio of A to B in the herbicidal composition is 1:4 to 2:1; when B is flumetsulam, the weight ratio of A to B in the herbicidal composition is 1:5 to 2:1; when B is fenoxaprop-P-ethyl, clodinafop-propargyl, pinoxaden or cloquintocet-mexyl, the weight ratio of A to B in the herbicidal composition is 1:15 to 1:2; when B is chlorotoluron or isopropyl, the weight ratio of A to B in the herbicidal composition is 1:150 to 1:15; when B is fluroxypyr, the weight ratio of A to B in the herbicidal composition is 1:30 to 1:2; when B is fluroxypyr-isooctyl, the weight ratio of A to B in the herbicidal composition is 1:50 to 1:5; when B is 2-methyl-4-chlorophenoxyacetic acid, the weight ratio of A to B in the herbicidal composition is 1:60 to 1:5; when B is 2-methyl-4-chlorophenoxyacetic acid-isooctyl, the weight ratio of A to B in the herbicidal composition is 1:120 to 1:30; when B is 2,4-dichlorophenoxyacetic acid, the weight ratio of A to B in the herbicidal composition is 1:150 to 1:10; when B is dicamba, the weight ratio of A to B in the herbicidal composition is 1:60 to 1:8; when B is benfuresate, the weight ratio of A to B in the herbicidal composition is 1:600 to 1:50; when B is glufosinate-ammonium, the weight ratio of A to B in the herbicidal composition is 1:80 to 1:

8.

3. The herbicidal composition according to claim 2, wherein, when B is picolinafen, the weight ratio of A to B in the herbicidal composition is 1:20 to 1:2; When B is bispyribac-methyl, flupyrazole, bensulfuron-methyl, or pyrimisulfuron-methyl, , When using cypermethrin or cyclohexane, the weight ratio of A to B in the herbicidal composition is 1:8 to 1:1; when B is dichloroisonixin, amicarbazone or fluorotolan, the weight ratio of A to B in the herbicidal composition is 1:20 to 1:4; when B is pyraflufen-ethyl, Beflubutamid-M, flurtamone, or metalaxyl-M, the weight ratio of A, B in the herbicidal composition is 1 : 15 ~ 1 : 2; when B is benzenesulfonuron, mesosulfuron, pyroxasulfone or flurotyl, the weight ratio of A to B in the herbicidal composition is 1:1 to 5:1; when B is when B is pendimethalin, s- metamifop, acetochlor or glyphosate, the weight ratio of A, B in the herbicidal composition is 1:80-1:8; when B is fluthiacet-methyl, the weight ratio of A to B in the herbicidal composition is 1:1 to 8:1; when B is thifensulfuron-methyl, the weight ratio of A to B in the herbicidal composition is 1:4 to 1:1; when B is flumetsulam, the weight ratio of A to B in the herbicidal composition is 1:5 to 1:1; when B is fenoxaprop-P-ethyl, clodinafop-propargyl, pinoxaden or cloquintocet-mexyl, the weight ratio of A to B in the herbicidal composition is 1:10 to 1:2; when B is chlorotoluron or isopropyl, the weight ratio of A to B in the herbicidal composition is 1:120 to 1:15; ​ When B is fluroxypyr, the weight ratio of A, B in the herbicidal composition is 1:20~1:2; When B is fluroxypyr-methyl, the weight ratio of A, B in the herbicidal composition is 1:30~1:5; When B is 2-methyl-4-chlorophenoxyacetic acid, the weight ratio of A, B in the herbicidal composition is 1:50~1:5; When B is 2,4-D ester, the weight ratio of A, B in the herbicidal composition is 1:100~1:30; When B is 2,4-D ester, the weight ratio of A, B in the herbicidal composition is 1:100~1:30; When B is 2,4-D ester, the weight ratio of A, B in the herbicidal composition is 1:100~1:30; When B is chlorimuron-ethyl, the weight ratio of A, B in the herbicidal composition is 1:300~1:50; When B is glufosinate-ammonium, the weight ratio of A, B in the herbicidal composition is 1:60~1:

8.

4. The herbicidal composition according to claim 3, wherein, When B is bispyribac-methyl, flupyrazole, bensulfuron-methyl, or pyrimisulfuron-methyl, , When using cyprodinil or cyclohexane, the weight ratio of A to B in the herbicidal composition is 1:5 to 1:1; When B is benzenesulfonamide, the weight ratio of A, B in the herbicidal composition is 1:1~2:1; when B is pyraflufen-ethyl, Beflubutamid-M, flurtamone, or metalaxyl-M, the weight ratio of A, B in the herbicidal composition is 1 : 10 ~ 1 : 2; When B is benzenesulfonamide, the weight ratio of A, B in the herbicidal composition is 1:1~2:1; when B is when B is pendimethalin, s- metamifop, acetochlor or glyphosate, the weight ratio of A, B in the herbicidal composition is 1:60-1:8; When B is benzenesulfonamide, the weight ratio of A, B in the herbicidal composition is 1:1~2:1; When B is benzenesulfonamide, the weight ratio of A, B in the herbicidal composition is 1:1~2:1; When B is benzenesulfonamide, the weight ratio of A, B in the herbicidal composition is 1:1~2:1; When B is benzenesulfonamide, the weight ratio of A, B in the herbicidal composition is 1:1~2:1; When B is benzenesulfonamide, the weight ratio of A, B in the herbicidal composition is 1:1~2:1; When B is benzenesulfonamide, the weight ratio of A, B in the herbicidal composition is 1:1~2:1; When B is benzenesulfonamide, the weight ratio of A, B in the herbicidal composition is 1:1~2:1; When B is benzenesulfonamide, the weight ratio of A, B in the herbicidal composition is 1:1~2:1; When B is benzenesulfonamide, the weight ratio of A, B in the herbicidal composition is 1:1~2:1; When B is benzenesulfonamide, the weight ratio of A, B in the herbicidal composition is 1:1~2:1; When B is benzenesulfonamide, the weight ratio of A, B in the herbicidal composition is 1:1~2:1; The mass percentage of A and B in the herbicidal composition is 1-95% of the total amount. ​ ​ 5. A herbicidal composition comprising a pyrimidyl carboxyl oxime derivative according to any one of claims 1 to 4, characterized in that ​ 6. A herbicidal composition comprising a pyrimidyl formhydroxamyl derivative according to claim 5, characterized in that, The mass percentage of A and B in the herbicidal composition is 10-80% of the total amount.

7. A herbicidal composition comprising a pyrimidyl carboxyl oxime derivative according to any one of claims 1 to 4, characterized in that, The herbicidal composition further comprises conventional adjuvants.

8. A herbicidal composition comprising a pyrimidyl formhydroxamyl derivative according to claim 7, characterized in that, The conventional adjuvants include carriers and / or surfactants.

9. A herbicidal composition comprising a pyrimidyl carboxyl oxime derivative according to any one of claims 1 to 4, characterized in that, The herbicidal composition further comprises at least one safener.

10. A herbicidal composition comprising a pyrimidyl formhydroxamyl derivative according to claim 9, characterized by, The safener is selected from one or more of isoxadifen-ethyl, cyprosulfamide, metcamifen, furilazole, and cloquintocet.

11. A herbicidal composition comprising a pyrimidyl carboxyl oxime derivative according to any one of claims 1 to 4, characterized in that, The specific formulation of the herbicidal composition is dispersible oil suspension, aqueous suspension, suspoemulsion, wettable powder, emulsifiable concentrate, water dispersible granule, aqueous emulsion, or microemulsion.

12. Use of the herbicidal composition comprising the pyrimidine formyl oxime derivative according to any one of claims 1 to 11 for controlling weeds.

13. A method for controlling the growth of unwanted plants, comprising applying the herbicidal composition comprising the pyrimidine formyl oxime derivative according to any one of claims 1 to 11 to the plants or the area where the plants grow.

14. A method for controlling undesirable plant growth according to claim 13, wherein, Applying the herbicidal composition comprising the pyrimidine formyl oxime derivative according to any one of claims 1 to 11 to the plant parts.

15. A method for controlling undesirable plant growth according to claim 13, wherein, Applying the herbicidal composition comprising the pyrimidine formyl oxime derivative according to any one of claims 1 to 11 to the plant seeds.

Citation Information

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