WO2009116558A1 - Dérivé de 1-phényl-5-difluorométhylpyrazole-4-carboxamide et herbicide contenant le dérivé en tant qu’ingrédient actif - Google Patents

Dérivé de 1-phényl-5-difluorométhylpyrazole-4-carboxamide et herbicide contenant le dérivé en tant qu’ingrédient actif Download PDF

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WO2009116558A1
WO2009116558A1 PCT/JP2009/055251 JP2009055251W WO2009116558A1 WO 2009116558 A1 WO2009116558 A1 WO 2009116558A1 JP 2009055251 W JP2009055251 W JP 2009055251W WO 2009116558 A1 WO2009116558 A1 WO 2009116558A1
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group
formula
compound
present
active ingredient
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PCT/JP2009/055251
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Japanese (ja)
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至 岡田
麻紀子 牛江
貴史 中山
英世 藤井
誠司 柿沼
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アグロカネショウ株式会社
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION 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
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles

Definitions

  • the present invention relates to novel pyrazole carboxamide derivatives and herbicides containing them as active ingredients.
  • weed control by herbicides is essential for labor saving, improvement of crop productivity, and landscape protection in cultivation of agricultural and horticultural crops and in management of green areas such as parks, recreation facilities and roads. For this reason, research and development of herbicides has been actively carried out for many years, and various herbicides have been put to practical use at present. However, the emergence of weeds that have acquired resistance to conventionally used herbicides has also become a problem.
  • weeds such as mizuaoi, azenas, izohakobe, chikasigusa, anifish, and konagi are all over the place Control of these weeds is becoming more difficult every year.
  • environmental pollution such as pollution damage to the surrounding cultivation land due to rainfall infiltration migration or runoff, gasification, etc., groundwater contamination, pollution damage to subsequent crops due to soil residue is also a problem.
  • Patent Document 1 As compounds most similar to the present invention, the following herbicidally active compounds are known (eg, Patent Document 1 and Non-patent Documents 1 and 2).
  • this compound remains undegraded in the soil for a long period of time and there is a risk of soil contamination and adverse effects on subsequent crops, and the effect of reducing the amount of sprayed water is inferior. It has not been put into practical use because it has problems such as the difficulty in securing areas and the effect of large-scale spraying situations or uneven spraying.
  • pyrazole carboxamide derivatives are known to have insecticidal, acaricidal, bactericidal, herbicidal or medicinal activity, depending on the type of three substituents on the pyrazole ring and the amino group of carboxamide moiety.
  • the following microbicides have been developed as 1-alkylpyrazole-4-carboxamide derivatives (for example, Patent Documents 2 to 8).
  • Patent Documents 12 to 13 The following compounds have been developed as acaricides (eg, Patent Documents 12 to 13).
  • herbicidally active compounds are known as 1-phenylpyrazole-4-carboxamide (for example, Patent Documents 14 to 15).
  • acaricides are disclosed as pyrazole-5-carboxamide derivatives (for example, Patent Document 16).
  • insecticides for example, insecticides and acaricides (for example, Patent Document 17).
  • Patent Document 20 reports N-aralkyl-1-phenylpyrazole-3-carboxamide derivatives having insecticidal and acaricidal activity.
  • Patent Document 21 describes N-hydroxy-4-halo-5-unsubstituted-1-phenylpyrazole-3-carboxamide derivatives, for example, Patent Document 22.
  • N-alkyl-4-unsubstituted-5-alkyl-1-phenylpyrazole-3-carboxamide derivatives are also disclosed in, for example, Patent Document 23, N-alkyl-4-unsubstituted-1,5- Diphenylpyrazole-3-carboxamide derivatives have been described.
  • Patent Document 24 describes the herbicidal activity of N-alkyl-4-halo-1,5-diphenylpyrazole-3-carboxamide.
  • N-alkyl-4-unsubstituted-5-alkoxy-1-phenylpyrazole-3-carboxamide derivatives having pharmaceutical activity are described in Non-Patent Document 3 and Non-Patent Document 4, but the description related to pesticidal activity There is no.
  • N-methyl-4-bromo-5-methoxy-1-phenylpyrazole-3-carboxamide is described, for example, in Non-Patent Document 5, but it has no pharmaceutically activity but also completely describes pesticide activity.
  • 1-phenylpyrazole-3-carboxamide derivatives for example, compounds having the following bactericidal activity are disclosed (for example, Patent Documents 25 to 31).
  • the present invention provides a highly safe and useful chemical substance as an active ingredient of a herbicide, which exhibits high control effect on various weeds and has reduced problems such as soil contamination and effects on subsequent crops. It is.
  • the present invention relates to a 1-phenyl-5-difluoromethylpyrazole-4-carboxamide derivative represented by and a herbicide containing the derivative as an active ingredient.
  • R 1 and R 2 each represent a hydrogen atom, a halogen atom, a C 1 to C 4 alkyl group, a trifluoromethyl group, a nitro group, a cyano group, C 1 to an alkoxy group having C 4, difluoromethoxy group, trifluoromethoxy group, a difluoromethylthio group, a trifluoromethylthio group, difluoromethyl sulfinyl group, a difluoromethyl sulfonyl group, trifluoromethyl sulfinyl group, or a trifluoromethylsulfonyl group.
  • halogen atom a fluorine atom, a chlorine atom, a bromine atom, an iodine atom etc. are mentioned suitably, for example.
  • C 1 to C 4 alkyl group for example, methyl group, ethyl group, n-propyl group, isopropyl group, cyclopropyl group, n-butyl group, isobutyl group, sec-butyl group, t-butyl group, etc.
  • the alkoxy group of C 1 ⁇ C 4, for example, a methoxy group, an ethoxy group, n- propoxy group, isopropoxy group, n- butoxy group, isobutoxy group, sec- butoxy group, C 1 such as t- butoxy such as linear or branched alkoxy group having ⁇ C 4 are preferably exemplified.
  • R 1 is a hydrogen atom, a chlorine atom, a bromine atom, a fluorine atom, a difluoromethoxy group, a trifluoromethoxy group or the like
  • R 2 is preferably a hydrogen atom.
  • R 3 represents a hydroxyl group, a C 1 to C 4 alkoxy group, an amino group, a C 1 to C 4 alkylamino group, a C 2 to C 4 N, N-dialkylamino group or a C 2 to C 4 N -Represents an alkyl N-alkoxyamino group.
  • the range of the C 1 to C 4 alkoxy group is as described above, and examples thereof include a methoxy group, an ethoxy group, an n-propoxy group, an isopropoxyl group, an n-butoxy group, an isobutoxy group, and a sec-butoxy group.
  • a C 1 to C 4 linear or branched alkoxy group such as t-butoxy group.
  • the C 1 to C 4 alkylamino group is a C 1 to C 4 alkyl group wherein the alkyl group of the amino group is a C 1 to C 4 alkyl group.
  • Examples of such a C 1 to C 4 alkylamino group include a methylamino group and the like , C 1 -C 4 straight such as ethylamino group, n-propylamino group, isopropylamino group, cyclopropylamino group, n-butylamino group, isobutylamino group, sec-butylamino group, t-butylamino group, etc.
  • the C 2 -C 4 N, N-dialkylamino group is one in which the nitrogen atom of the amino group is substituted with two alkyl groups, and the range of the alkyl group is the total number of carbon atoms in the alkyl group Is 2 to 4, and specifically, for example, C 2 to C 4 N, N-dialkylamino groups such as dimethylamino, diethylamino, methylethylamino, methylpropylamino and the like are preferably mentioned.
  • N-alkyl N-alkoxyamino group for example, methylmethoxyamino group, methylethoxyamino group, methyl-n-propoxyamino group, ethylmethoxy group, n-propylmethoxy group and the like are preferable. It can be mentioned.
  • R 3 for example, a methylamino group or a cyclopropylamino group is preferable.
  • the compounds of the present invention represented by the above formula (I) are novel compounds.
  • the compound of the present invention can be produced, for example, according to the following reaction formula 1, in accordance with, for example, JP-A-60-172,967 (Patent Document 1). Reaction formula 1
  • R 1 , R 2 and R 3 are as defined in the above formula (I), and X represents a chlorine atom, a bromine atom, a hydroxyl group, a methoxy group, an ethoxy group or a propoxy group.
  • X represents a chlorine atom or a bromine atom
  • a solvent for example, benzene, or an aromatic hydrocarbon such as toluene or xylene; acetone, methyl ethyl ketone, methyl isobutyl ketone or the like Ketones; halogenated hydrocarbons such as chloroform and methylene chloride; water; esters such as methyl acetate and ethyl acetate; or tetrahydrofuran, acetonitrile, dioxane, N, N-dimethylformamide, N-methylpyrrolidone or dimethyl sulfoxide, etc.
  • the reaction can be performed in the presence of a base at, for example, 0 ° C. to 30 ° C., preferably 0 ° C. to 5 ° C., using a polar solvent of As a base, for example, sodium hydroxide, potassium hydroxide, pyridine or triethylamine can be used.
  • a base for example, sodium hydroxide, potassium hydroxide, pyridine or triethylamine can be used.
  • X is a hydroxyl group, a methoxy group, an ethoxy group or a propoxy group
  • the reaction can be carried out at 5 to 100.degree. C., preferably 20 to 80.degree.
  • the solvent was distilled off under reduced pressure and water was added. After that, extract with water-insoluble benzene, aromatic hydrocarbons such as toluene and xylene; halogenated hydrocarbons such as chloroform and methylene chloride; esters such as ethyl acetate, and wash with saturated saline, and then anhydrous sodium sulfate After drying with a desiccant such as, the solvent may be distilled off under reduced pressure.
  • aromatic hydrocarbons such as toluene and xylene
  • halogenated hydrocarbons such as chloroform and methylene chloride
  • esters such as ethyl acetate, and wash with saturated saline, and then anhydrous sodium sulfate
  • the solvent may be distilled off under reduced pressure.
  • R 1 , R 2 and R 4 are as defined in the above formula (III).
  • the above reaction can be carried out in the presence or absence of a solvent and a base.
  • the solvent is not particularly limited as long as it does not directly participate in the reaction, and examples thereof include benzene, aromatic hydrocarbons such as toluene and xylene; halogenated hydrocarbons such as chloroform and dichloromethane; water; methyl acetate And esters such as ethyl acetate; polar solvents such as acetonitrile, N, N-dimethylformamide, N-methyl pyrrolidone and dimethyl sulfoxide; ethers such as tetrahydrofuran, dioxane and diisopropyl ether; methanol, ethanol, propanol, ethylene glycol and the like Or mixed solvents of the above solvents.
  • Examples of the base include alkali metal hydrates such as sodium hydroxide and potassium hydroxide; alkaline earth metal hydroxides such as magnesium hydroxide and calcium hydroxide; alkali metal carbonates such as sodium carbonate and potassium carbonate Sodium hydrogen carbonate; alkali metal hydrogen carbonates such as potassium hydrogen carbonate; alkaline earth metal carbonates such as calcium carbonate and magnesium carbonate; metal alkoxides such as sodium methoxide and sodium ethoxide.
  • the reaction temperature is, for example, 5 to 100 ° C., preferably 0 to 50 ° C.
  • mineral acids such as hydrochloric acid and sulfuric acid
  • acidification with organic acids such as acetic acid and propionic acid
  • the solvent is distilled off under reduced pressure, water is added, and then benzene insoluble in water, aromatic hydrocarbons such as toluene and xylene; halogen based hydrocarbons such as chloroform and dichloromethane
  • Extraction with an ester such as ethyl acetate and the like, washing with saturated brine, drying with a desiccant such as anhydrous sodium sulfate, and evaporation of the solvent under reduced pressure may be carried out.
  • the above reaction can be carried out in the presence or absence of a solvent and in the presence of a base.
  • a solvent include water; alcohols such as methanol, ethanol, propanol and ethylene glycol, and mixed solvents of the above solvents.
  • the base include alkali metal hydroxides such as sodium hydroxide and potassium hydroxide; alkaline earth metal hydroxides such as magnesium hydroxide and calcium hydroxide; alkali metal carbonates such as sodium carbonate and potassium carbonate; hydrogen carbonate Examples thereof include alkali metal carbonates such as sodium and potassium hydrogen carbonate; and alkaline earth metal carbonates such as calcium carbonate and magnesium carbonate.
  • the reaction temperature is, for example, 5 to 150 ° C., preferably 10 to 110 ° C.
  • the precipitate is acidified after being acidified with a mineral acid such as hydrochloric acid or sulfuric acid; acetic acid or an organic acid such as propionic acid It may be filtered and washed with water and then dried.
  • R 1 and R 2 are as defined in the formula (I), and Z represents a chlorine atom or a bromine atom.
  • the compound of formula (VI) is reacted with a halogenating agent to give a compound of formula (VII).
  • the above reaction can be carried out in the presence or absence of a solvent.
  • the solvent is not particularly limited as long as it does not directly participate in the reaction, and examples thereof include benzene, aromatic hydrocarbons such as toluene and xylene; halogenated hydrocarbons such as chloroform and dichloromethane.
  • halogenating agent examples include thionyl chloride, thionyl bromide, oxalyl chloride, oxalyl bromide, phosphorus pentachloride, phosphorus pentabromide, phosphorus trichloride and the like.
  • the reaction temperature is, for example, 5 to 100 ° C., preferably 20 to 90 ° C.
  • the reaction solution is concentrated under reduced pressure, and the obtained residue is dissolved with a hydrocarbon such as hexane or heptane which does not dissolve the desired product very much. It may be dried after washing.
  • the herbicide of the present invention containing the compound of the present invention represented by the formula (I) as an active ingredient has an excellent herbicidal effect on various weeds of agricultural land and non-agricultural land. Above all, it is useful as an active ingredient of a foliage treating herbicide for upland field annual weeds.
  • weeds for example, crabgrass, enokologsa, pokeweed, bluefish, shiroza, ichibi, chickweed, morning glory and the like can be mentioned.
  • weeds to be controlled by the compounds of the present invention are not limited to those exemplified above.
  • the herbicide of the present invention containing the compound of the present invention represented by the formula (I) as an active ingredient has high safety to crops such as wheat, barley, sorghum, corn, cotton and beets.
  • the compound of the present invention represented by the formula (I) may be used alone, but it is preferably used as a composition to which a pesticide adjuvant widely used in the art is added.
  • the dosage form of the herbicide is not particularly limited, for example, the form of an emulsion, a wettable powder, a powder, a flowable, a fine granule, a granule, a tablet, an oil and the like is preferable.
  • One or two or more of the compounds of the present invention can be blended as an active ingredient.
  • Pesticide adjuvants used to produce herbicides are, for example, substances having effects such as enhancement of the effect of herbicide, stabilization, improvement of dispersibility, and enhancement of crop safety, for example, carriers (Diluents), spreaders, emulsifiers, wetting agents, dispersants, disintegrants, wetting agents and the like can be used.
  • Liquid carriers include, for example, water; aromatic hydrocarbons such as toluene and xylene; alcohols such as methanol, butanol and glycol; ketones such as acetone; amides such as dimethylformamide; sulfoxides such as dimethyl sulfoxide; Naphthalene; cyclohexane; animal and vegetable oils; or fatty acids and the like can be mentioned.
  • examples of the solid carrier include clay, kaolin, talc, diatomaceous earth, silica, calcium carbonate, montmorillonite, bentonite, feldspar, quartz, alumina, saw dust, nitrocellulose, starch, gum arabic and the like.
  • emulsifying agent and the dispersing agent usual surfactants can be used.
  • anionic surfactants such as higher alcohol sodium sulfate, stearyltrimethyl ammonium chloride, polyoxyethylene alkylphenyl ether, lauryl betaine and the like;
  • An ionic surfactant; a nonionic surfactant; or a zwitterionic surfactant etc. can be used.
  • spreading agents such as polyoxyethylene fatty acid ester and polyoxyethylene alkyl ester
  • wetting agents such as dialkyl sulfosuccinate
  • fixing agents such as carboxyl methyl cellulose and polyvinyl alcohol
  • collapse such as sodium lignin sulfonate and sodium lauryl sulfate Agents can be used.
  • the content of the active ingredient in the herbicide of the present invention is, for example, selected from the range of 0.01 to 99.5%, and may be suitably determined according to various conditions such as the formulation form, application method and the like.
  • the emulsion for example, about 1 to 90% by mass, preferably 10 to 40% by mass
  • in the wettable powder for example, about 1 to 90% by mass, preferably 10 to 80% by mass
  • about 0.5 to 20% by mass preferably 1 to 10% by mass
  • a flowable for example, about 1 to 90% by mass, preferably 10 to 50% by mass. It is preferred to manufacture.
  • an emulsion of a stock solution can be prepared by mixing a solvent, a surfactant and the like with the compound of the present invention which is an active ingredient, and this stock solution is Can be diluted and applied.
  • the compound of the present invention, which is the active ingredient can be mixed with water, surfactant, etc. to produce a stock solution, and this stock solution is further diluted with water to a predetermined concentration when used. Can be applied.
  • the compound of the present invention as an active ingredient, a solid carrier, a surfactant and the like can be mixed and manufactured, and when used, it can be applied diluted with water to a predetermined concentration.
  • the compound of the present invention as an active ingredient, a solid carrier and the like can be mixed and applied as they are.
  • the manufacturing method of each above-mentioned formulation form is not limited to the above-mentioned thing, those skilled in the art can select suitably according to the kind of an active ingredient, the purpose of application, etc.
  • herbicide of the present invention other herbicides, insecticides, acaricides, fungicides, growth regulators, fertilizers, as long as the activity of the compound of the present invention of the formula (I) which is the active ingredient is not impaired.
  • the compounds of the present invention can be used in the same manner as conventional herbicides, and for example, soil treatment or foliage treatment is carried out using the compounds of the present invention before germination, early germination and growth stage of upland weeds. be able to.
  • the application amount of the herbicide of the present invention can be appropriately selected depending on the application method, purpose, time, weeding condition and the like, but the amount of active ingredient is usually 0.001 kg to 10 kg per hectare, for example. Is preferably 0.003 kg to 3 kg.
  • Example 2 Synthesis of 1- (4-chlorophenyl) -5-difluoromethylpyrazole-4-carboxylic acid
  • Ethyl 1- (4-chlorophenyl) -5-difluoromethylpyrazole-4-carboxylate obtained in Example 1 A mixture of 9.02 g, 2.40 g of sodium hydroxide, 40 ml of ethyl alcohol and 40 ml of water was heated to reflux for 1 hour. After cooling to room temperature, hydrochloric acid is added to acidify and crystals are collected by filtration, washed with water and dried to obtain 8.10 g of the compound of the present invention (No. 4) described in Table 1. The melting point was 140-142 ° C.
  • Example 3 Synthesis of N-methyl-1- (4-chlorophenyl) -5-difluoromethylpyrazole-3-carboxamide 1- (4-chlorophenyl) -5-difluoromethylpyrazole-4-obtained in Example 2
  • the solution was heated under reflux for 1 hour in 5 ml of thionyl chloride and concentrated under reduced pressure.
  • the resulting residue was added to 1.16 g of 40% aqueous methylamine solution and stirred at room temperature for 1 hour.
  • the mixture was extracted with ethyl acetate, and the organic layer was washed with saturated brine and then dried over anhydrous sodium sulfate. After concentration under reduced pressure, the resulting residue was washed with hexane to obtain 0.35 g of the compound of the present invention (No. 31) described in Table 2.
  • the melting point was 167-169 ° C.
  • Example 4 Synthesis of Nn-propyl-1- (4-chlorophenyl) -5-difluoromethylpyrazole-4-carboxamide 1- (4-chlorophenyl) -5-difluoromethylpyrazole-4-obtained in Example 1 3.01 g of ethyl carboxylate and 0.18 g of n-propylamine were stirred in 10 ml of methanol at room temperature for 18 hours. The mixture was concentrated under reduced pressure, and the obtained residue was purified by silica gel column chromatography to obtain 2.50 g of a compound (No. 33) described in Table 2 below. The melting point was 128-130 ° C. Other than that, the compound of the present invention was prepared similarly. Tables 1 and 2 below describe the compounds of the invention prepared according to the examples.
  • formulation examples of a herbicide containing the compound of the present invention as an active ingredient are shown.
  • the scope of the present invention is not limited at all by the following formulation examples.
  • all being "part" in an Example represents a mass part.
  • Formulation Example 2 Hydrating agent Compound of the present invention (20 parts), Carplex # 80 (20 parts), ST kaolin clay (50 parts), sodium lignin sulfonate (5 parts) and Lunox P-as a wetting agent 65 L (5 parts) was uniformly mixed and ground in a jet air mill to obtain a wettable powder.
  • Formulation Example 3 Granule
  • the compound of the present invention (5 parts), bentonite (30 parts), clay (60 parts) and sodium lignin sulfonate (5 parts) were uniformly ground and mixed, water was added and thoroughly mixed. Thereafter, the mixture was extruded and granulated, and dried and sized to obtain granules.
  • the compounds of the present invention show excellent herbicidal effects even when the amount of water sprayed is small, and are stable even in areas where water is difficult to secure, in large-scale spraying situations, and also in uneven spraying. Exhibit excellent weeding effects.
  • the 1-phenyl-5-difluoromethylpyrazole-4-carboxamide derivative compound of the present invention has an excellent control effect on various weeds and is effective as a herbicide.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
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Abstract

L’invention concerne un dérivé de 1-phényl-5-difluorométhylpyrazole-4-carboxamide ayant une excellente activité herbicide. Le dérivé est représenté par la formule (I). (Dans la formule, R1 et R2 représentent chacun indépendamment un atome d’hydrogène, un atome d’halogène, un atome d’halogène, un groupe alkyle en C1 à C4, un groupe trifluorométhyle, un groupe nitro, un groupe cyano, un groupe alcoxy en C1 à C4, un groupe difluorométhoxy, un groupe trifluorométhoxy, un groupe difluorométhylthio, un groupe trifluorométhylthio, un groupe difluorométhylsulfinyle, un groupe difluorométhylsulfonyle, un groupe trifluorométhylsulfinyle ou un groupe trifluorométhylsulfonyle; et R3 représente un groupe hydroxy, un groupe alcoxy en C1 à C4, un groupe amine, un groupe alkylamino en C1 à C4, un groupe N,N-dialkylamino en C2 à C4 ou un groupe N-alkyl-N-alcoxyamino en C2 à C4.)
PCT/JP2009/055251 2008-03-19 2009-03-18 Dérivé de 1-phényl-5-difluorométhylpyrazole-4-carboxamide et herbicide contenant le dérivé en tant qu’ingrédient actif WO2009116558A1 (fr)

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