WO2022095816A1 - Composition herbicide ternaire comprenant un composé oxyiminoaryle substitué par un dérivé acide carboxylique et son utilisation - Google Patents

Composition herbicide ternaire comprenant un composé oxyiminoaryle substitué par un dérivé acide carboxylique et son utilisation Download PDF

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WO2022095816A1
WO2022095816A1 PCT/CN2021/127863 CN2021127863W WO2022095816A1 WO 2022095816 A1 WO2022095816 A1 WO 2022095816A1 CN 2021127863 W CN2021127863 W CN 2021127863W WO 2022095816 A1 WO2022095816 A1 WO 2022095816A1
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WIPO (PCT)
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herbicidal composition
methyl
active ingredient
ternary
inhibitors
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PCT/CN2021/127863
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English (en)
Chinese (zh)
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李平生
彭学岗
赵德
张景远
金涛
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青岛清原化合物有限公司
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Publication of WO2022095816A1 publication Critical patent/WO2022095816A1/fr

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    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
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    • A01N43/6531,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
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    • A01N43/00Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
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    • A01N43/681,3,5-Triazines, not hydrogenated and not substituted at the ring nitrogen atoms with two or three nitrogen atoms directly attached to ring carbon atoms
    • A01N43/70Diamino—1,3,5—triazines with only one oxygen, sulfur or halogen atom or only one cyano, thiocyano (—SCN), cyanato (—OCN) or azido (—N3) group directly attached to a ring carbon atom
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    • A01N43/64Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
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    • A01N43/00Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
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    • A01N43/80Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2
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    • A01N47/00Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
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    • A01N47/28Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
    • A01N47/30Derivatives containing the group >N—CO—N aryl or >N—CS—N—aryl
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Definitions

  • the invention belongs to the field of pesticides, and in particular relates to a ternary herbicidal composition comprising a carboxylic acid derivative-substituted oxyimino aryl compound and its application.
  • Chemical weeding is the most economical and effective method for weed control in farmland.
  • the long-term continuous and high-dose use of chemical herbicides of a single species or single mode of action is likely to cause problems such as weed resistance and resistance evolution.
  • the rational compounding or compounding of herbicide compounds has the advantages of expanding the weed spectrum, improving the control effect, delaying the occurrence and development of drug resistance and drug resistance of weeds, etc., and is one of the most effective methods to solve the above problems. Therefore, there is an urgent need to develop herbicidal compositions with high safety, broad herbicidal spectrum, synergistic effects and solving the problem of resistant weeds.
  • the present invention provides a ternary herbicidal composition
  • a ternary herbicidal composition comprising an oxyimino aryl compound substituted with a carboxylic acid derivative and an application thereof.
  • Leaf and other weed problems have the characteristics of expanding the herbicidal spectrum, reducing the application amount, producing synergistic effects and solving resistant weeds.
  • a ternary herbicidal composition comprising a carboxylic acid derivative-substituted oxyimino aryl compound, characterized in that it comprises herbicidal effective amounts of active ingredient A, active ingredient B and active ingredient C, wherein,
  • Active ingredient A is N-(2-aminoethyl)-2-aminoethyl-N-(2-aminoethyl)-2-aminoethyl-N-(2-aminoethyl)-2-aminoethyl-N-(2-aminoethyl)-2-aminoethyl-N-(2-aminoethyl)-2-aminoethyl
  • the active ingredients B and C are respectively selected from any one of the following types of compounds and another compound of different types:
  • VLCFA inhibitors Acetochlor (CAS No.: 34256-82-1), Metolachlorsperm (CAS No.: 87392-12-9), Meafenpyr (CAS No.: 447399-55- 5), metolachlor (CAS number: 86763-47-5), fenfenacil (CAS number: 73250-68-7), dimethachlor (CAS number: 87674-68-8), Butachlor (CAS No.: 23184-66-9), Pretochlor (CAS No.: 51218-49-6);
  • Microtubule assembly inhibitor pendimethalin (CAS No.: 40487-42-1), Zhongdingling (CAS No.: 33629-47-9);
  • EPSPS inhibitor glyphosate (CAS number: 1071-83-6);
  • GS inhibitor glufosinate-ammonium (CAS number: 77182-82-2);
  • PSII inhibitors atrazine (CAS number: 1912-24-9), terbutin (CAS number: 5915-41-3), mezotrione (CAS number: 21087-64-9), isocyanurate (CAS number: 21087-64-9) Proprion (CAS No.: 34123-59-6), Chlormelon (CAS No.: 15545-48-9), Azafenazone (CAS No.: 129909-90-6), Diuron (CAS No.: 330) -54-1), barnyardgrass (CAS number: 709-98-8);
  • HPPD inhibitor isoxaflutole (CAS number: 141112-29-0), mesotrione (CAS number: 104206-82-8);
  • DOXP inhibitor clomazone (CAS number: 81777-89-1), bixlozone (CAS number: 81777-95-9);
  • PDS inhibitor diflufenac (CAS number: 83164-33-4);
  • PPO inhibitor sulfentrazone (CAS number: 122836-35-5), oxadiazon (CAS number: 19666-30-9);
  • ALS inhibitors penoxsulam (CAS number: 219714-96-2), thiazosulfuron (CAS number: 317815-83-1), imazamox (CAS number: 114311-32) -9), nicosulfuron (CAS number: 111991-09-4), rimsulfuron (CAS number: 122931-48-0), chlorpyrisulfuron (CAS number: 100784-20-1), Sulfentrazone (CAS No.: 98967-40-9), Sulfentrazone (CAS No.: 147150-35-4), Imazamil (CAS No.: 104098-48-8), Thifensulfuron-methyl (CAS number: 79277-27-3), flufenoxsulam (CAS number: 874195-61-6), bensulfuron-methyl (CAS number: 83055-99-6), pyrazosulfuron (CAS number: 83055-99-6) 93697-74-6);
  • ACCase inhibitors quizalofop-p-ethyl (CAS number: 100646-51-3), clethodim (CAS number: 99129-21-2);
  • the weight ratio of A, B and C is 1 ⁇ 200:1 ⁇ 1000:0.1 ⁇ 5000, 5 ⁇ 150:5 ⁇ 600:1 ⁇ 3000, 8 ⁇ 120:10 ⁇ 500:5 ⁇ 1000, 10 ⁇ 100 : 20 ⁇ 400:10 ⁇ 800, 20 ⁇ 90:30 ⁇ 300:30 ⁇ 600, 25 ⁇ 80:80 ⁇ 200:50 ⁇ 300 or 30 ⁇ 60:100 ⁇ 150:100 ⁇ 200.
  • the mass percentage content of A, B and C in the herbicidal composition accounts for 1-95% of the total, preferably 10-80%.
  • the herbicidal composition also includes conventional adjuvants including carriers and/or surfactants.
  • carrier means an organic or inorganic, natural or synthetic substance. They facilitate application of the active ingredient, the carrier being generally inert and must be agriculturally acceptable, especially by the plants being treated.
  • the carrier 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, chlorine Substitute hydrocarbons, liquefied gas, etc.
  • Surfactants may include emulsifying agents, dispersing agents or wetting agents, which may be ionic or non-ionic. Examples which may be mentioned are the salts of polyacrylic acid, lignosulfonate, phenolsulfonic acid or naphthalenesulfonic acid, ethylene oxide with aliphatic alcohols or with aliphatic acids or with aliphatic amines with substituted phenols (particularly polymers of alkylphenols or arylphenols), sulfosuccinates, taurine derivatives (especially taurine alkyl esters) and phosphate esters of alcohols or polyhydroxyethylated phenols, Alkyl sulfonates, alkylaryl sulfonates, alkyl sulfates, lauryl ether sulfates, fatty alcohol sulfates, and sulfated hexadec-, heptadeca-, and octadecanol and
  • compositions may also contain various other components such as protective colloids, binders, thickeners, thixotropic agents, penetrants, stabilizers, chelating agents, dyes, colorants and polymers.
  • composition of the present invention can be mixed with the following active substances, such as known substances in "World Encyclopedia of Pesticide New Variety Technology", China Agricultural Science and Technology Press, 2010.9 and the documents cited herein.
  • active substances such as known substances in "World Encyclopedia of Pesticide New Variety Technology", China Agricultural Science and Technology Press, 2010.9 and the documents cited herein.
  • the herbicidal active substances mentioned below (Note: the name of the compound, or the common name according to the International Organization for Standardization (ISO), or the chemical name, with a code name when appropriate): Acetochlor, Butachlor, Alachlor, Metolachlor, Metolachlor, Spermatachlor, Pretolachlor, Toxachlor, Clochlor, Naprochlor, R-Levonachlor, Propionil , fenflufen, fenflufen, difenafen, dichlorfen, fenbutafen, brombutafen, dimethafen, high-efficiency dimethafen, ethoxy
  • the herbicidal composition further comprises at least one safener selected from:
  • Dichlorophenylpyrazole carboxylic acid derivatives preferred compounds are, for example, ethyl 1-(2,4-dichlorophenyl)-5-methylpyrazole-3-carboxylate (S1-2), 1-(2,4-Dichlorophenyl)-5-isopropylpyrazole-3-carboxylic acid ethyl ester (S1-3), 1-(2,4-dichlorophenyl)-5-(1 ,1-Dimethyl-ethyl)pyrazole-3-carboxylic acid ethyl ester (S1-4), 1-(2,4-dichlorophenyl)-5-phenylpyrazole-3-carboxylic acid ethyl ester Esters (S1-5), and related compounds described in EP-A-333131 and EP-A-269806.
  • Triazole carboxylic acid (S1) compounds the preferred compound is for example fenchlorazole, namely 1-(2,4-dichlorophenyl)-5-trichloromethyl-(1H)-1 , 2,4-triazole-3-carboxylic acid ethyl ester (S1-6) and related compounds (see EP-A-174562 and EP-A-346620).
  • S2 8-quinolineoxyacetic acid (S2) compounds, preferably 1-methylhex-1-yl (5-chloro-8-quinolineoxy) acetate (S2-1, cloquintocet- mexyl), such as PM (pp. 195-196), (1,3-dimethylbutan-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) yl) acetate (S2-4), (5-chloro-8-quinolinyloxy) ethyl acetate (S2-5), (5-chloro-8-quinolinyloxy) methyl acetate (S2- 6), (5-chloro-8-quinolineoxy) allyl acetate (S2-7), 2-(2-propyleneiminooxy)-1-ethy
  • 5-chloro-8-quinolinyloxy)malonic acid compounds preferred compounds are for example (5-chloro-8-quinolinyloxy)diethyl malonate, (5-chloro-8 -quinolinyloxy)diallyl malonate, (5-chloro-8-quinolinyloxy)-malonate methylethyl ester and related compounds described in EP-A-0582198.
  • phenoxyacetic acid phenoxypropionic acid or aromatic carboxylic acid type 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) .
  • aromatic carboxylic acid type 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) .
  • the safeners are preferably bisfenoxazole acid (CAS: 163520-33-0), cyprosulfamide (CAS: 221667-31-8), pyraclostrobin (CAS: 135590-91-9), quinoquine (CAS: 135590-91-9) : 99607-70-2), one or more of gibberellic acid (CAS: 7-06-5), furilazole (CAS: 121776-33-8), metcamifen (CAS: 129531-12-0).
  • the abbreviated form of the generic name of the active compound includes in each case all customary derivatives, such as esters and salts, as well as isomers, in particular optical isomers, in particular one or more commercially available forms.
  • the common name denotes esters or salts, it also includes in each case all other customary derivatives, such as other esters and salts, free acids and neutral compounds, as well as isomers, especially optical isomers, especially in one or more commercially available forms.
  • the chemical names of compounds given represent at least one compound covered by the generic name, usually the preferred compound.
  • salts also include salts formed by the exchange of cations with hydrogen atoms in the sulfonamide group.
  • 2 methyl 4 chloride derivatives include but are not limited to: 2 methyl 4 chloride sodium salt, potassium salt, dimethylammonium salt, isopropylamine salt, etc., and 2 methyl 4 chloro methyl ester, ethyl ester, isooctyl ester, ethyl sulfide Esters, etc.
  • 2,4-D derivatives include, but are not limited to: 2,4-D salts such as sodium, potassium, dimethylammonium, triethanolammonium, isopropylamine, choline, etc., and 2,4 -D esters such as methyl ester, ethyl ester, butyl ester, isooctyl ester, etc.
  • the salts of the compounds are preferably in the form of the respective alkali metal, alkaline earth metal or ammonium salts, preferably the respective alkali metal salts, more preferably the respective sodium or potassium salts, Most preferably in the form of the respective sodium salts.
  • compositions of the present invention may be diluted or used directly by the user prior to use. Its preparation can be prepared by the usual processing method, that is, after mixing the active substance with a liquid solvent or a solid carrier, and then adding one or more of surfactants such as dispersing agent, stabilizer, wetting agent, adhesive, defoaming agent, etc. kind.
  • surfactants such as dispersing agent, stabilizer, wetting agent, adhesive, defoaming agent, etc. kind.
  • the specific formulations of the herbicidal composition are dispersible oil suspensions, water suspensions, suspoemulsions, wettable powders, emulsifiable concentrates, water dispersible granules (dry suspensions), water emulsions, and microemulsions.
  • 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 external conditions, such as temperature, humidity, properties of herbicides used, and the like. It can vary widely, eg between 0.001 and 1.0 kg/ha, or more active substance, but is preferably between 0.005 and 750 g/ha, especially between 0.005 and 500 g/ha.
  • compositions of the present invention can be applied by spraying to the foliage of the plants to be treated, ie to weeds, especially to surfaces that are infested or susceptible to infestation.
  • 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 plants, plant parts, plants The area where seeds or plants grow.
  • the herbicidal composition is used to selectively control weeds in useful crops, more preferably, the useful crops are transgenic crops or crops treated with genome editing technology.
  • the compounds of the present invention can be used to treat all plants and plant parts.
  • Plant varieties and cultivars can be obtained by conventional propagation and breeding methods or by genetic engineering methods.
  • Genetically modified plants are those in which a heterologous gene (transgene) has been stably integrated into the genome of the plant.
  • a transgene defined by its specific location in the plant genome is called a transformation event or transgenic event.
  • Genetically modified plant cultivars that can be treated according to the invention include those resistant to one or more biotic stresses (pests, such as nematodes, insects, mites, fungi, etc.) or abiotic stresses (drought, low temperature, soil salinization etc.), or it contains other desirable features. Plants can be genetically modified to exhibit traits such as herbicide tolerance, insect tolerance, modified oil characteristics, or drought tolerance. Information on available genetically modified plants comprising single gene transformation events or combinations of transformation events can be obtained, for example, from publicly available databases maintained by the United States Department of Agriculture.
  • composition of the present invention is environmentally friendly and is easily degraded in the environment.
  • the herbicidal composition of the present invention has low cost and convenient use, and its popularization and application have huge economic and social benefits.
  • the test soil was quantitatively filled to 3/4 of the pot, and then watered from the bottom of the pot to make the soil completely wet to saturation.
  • the pretreated weed seeds (Amaranthus thorn, Amaranthus amaranthus) were evenly and quantitatively sown on the surface, covered with soil 0.5-2cm according to the size of the seeds, and used 24 hours after sowing.
  • the desired active ingredient A comes from patent CN202010281666.4, and its preparation example is as follows:
  • the desired Active Ingredient B and Active Ingredient C are purchased from the reagent company.
  • the original medicines were all made of acetone as solvent, diluted with 0.1% emulsifier Tween-80 aqueous solution, and diluted with current use.
  • Each treatment was repeated 3 times, with 5 pots per treatment, and 30 weed seeds were sown in each pot.
  • the whole seedlings of surviving weeds were cut off along the soil surface with a blade, and the fresh weight of the weeds was weighed with an analytical balance. For dead weeds, the fresh weight is zero.
  • the investigation was conducted 15 days after treatment, and a total of 1 investigation was conducted.
  • Colby's test was used to evaluate the types of combined effects of any two or three combinations on weeds.
  • E (%) (fresh weight of weeds in the treatment area/fresh weight of weeds in the control area) ⁇ 100
  • X represents the weed survival rate of A when the dosage is P
  • Y represents the weed survival rate of B when the dosage is Q
  • E0 represents the theoretical weed survival rate of A+B when the dosage is (P+Q)
  • E represents Actual weed survival for each treatment.
  • X, Y, Z, and N respectively represent the actual survival rate of n single agents, and n is the number of compound herbicide varieties.
  • E0-E>10% it shows synergistic effect; when E0-E ⁇ -10%, it shows antagonism; when E0-E is between ⁇ 10%, it shows that there is additive effect.
  • the weeds were cultivated in pots, using a 180 ⁇ 140mm plastic nutrient bowl, placed in an enamel plate, and containing the surface soil (4/5 places) collected from the farmland that had been air-dried and sieved, and the soil humidity was initially controlled at 20%, select weed seeds with full and uniform grains, soak them in warm water at 25°C for 6 hours, and germinate them in a biochemical incubator (dark) at 28°C. Place the just white weed seeds evenly on the soil surface, according to the size of the seeds. Size and then cover with soil 0.5-1cm.
  • the original medicines were all made of acetone as solvent, diluted with 0.1% emulsifier Tween-80 aqueous solution, and diluted with current use.
  • Each treatment was repeated 3 times, with 5 pots per treatment, and 30 weed seeds were sown in each pot, for a total of 150 seeds per treatment.
  • test shared medicine once. After the 3 leaves of Papia chinensis, thinned the seedlings, kept 20 weeds in each pot, and kept 100 weeds in each treatment, and then continued to cultivate until 4-5 leaves were evenly sprayed on stems and leaves.
  • the cultured test materials were evenly placed on a platform with an area of 0.5m 2 , and the stems and leaves of the 3WP-2000 walking spray tower were sprayed with a spray volume of 450 kg/ha.
  • the spray pressure is 0.3MPa. After all the liquid medicine is sprayed, close the air valve, open the spray tower door after 30 seconds, and take out the nutrition bowl. Then open the air valve, spray 50ml of water, and clean the spray pipe.
  • the present invention unexpectedly finds that the composition is used for controlling broad-leaved weeds such as Amaranthus thorn and Amaranthus amaranthus, as well as grass weeds such as Pseudomonas auratus, etc.
  • broad-leaved weeds such as Amaranthus thorn and Amaranthus amaranthus
  • grass weeds such as Pseudomonas auratus, etc.
  • this synergistic effect is more significant at low doses, which can reduce the dosage of the drug, reduce the pollution to the environment, and reduce the cost of agricultural use by rational compounding. It is efficient and has good application prospects.

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  • Life Sciences & Earth Sciences (AREA)
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  • Wood Science & Technology (AREA)
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  • Environmental Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Pest Control & Pesticides (AREA)
  • Agronomy & Crop Science (AREA)
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Abstract

La présente invention appartient au domaine des pesticides, et concerne en particulier une composition herbicide ternaire comprenant un composé oxyiminoaryle substitué par un dérivé acide carboxylique et son utilisation. La composition herbicide ternaire comprend une quantité herbicide efficace d'un ingrédient actif A, d'un ingrédient actif B, et d'un ingrédient actif C, l'ingrédient actif A étant, et les ingrédients actifs B et C étant respectivement n'importe quel composé et un autre composé différent sélectionné parmi les types suivants : les inhibiteurs de VLCFA, les inhibiteurs d'assemblage des microtubules, les inhibiteurs EPSPS, etc. La composition peut efficacement réguler divers problèmes liés à des mauvaises herbes telles que de la famille des poacées ou des mauvaises herbes à larges feuilles, et présente les caractéristiques d'élargir le spectre herbicide, réduisant la quantité d'application, produisant des effets de synergie et résolvant les questions des mauvaises herbes résistantes, etc.
PCT/CN2021/127863 2020-11-06 2021-11-01 Composition herbicide ternaire comprenant un composé oxyiminoaryle substitué par un dérivé acide carboxylique et son utilisation WO2022095816A1 (fr)

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WO2023222831A1 (fr) 2022-05-20 2023-11-23 Syngenta Crop Protection Ag Compositions herbicides
WO2023222836A1 (fr) 2022-05-20 2023-11-23 Syngenta Crop Protection Ag Compositions herbicides
WO2023222834A1 (fr) 2022-05-20 2023-11-23 Syngenta Crop Protection Ag Compositions herbicides

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