WO2003029231A1 - Derives de trifluorobutene nematicide - Google Patents

Derives de trifluorobutene nematicide Download PDF

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Publication number
WO2003029231A1
WO2003029231A1 PCT/EP2002/010351 EP0210351W WO03029231A1 WO 2003029231 A1 WO2003029231 A1 WO 2003029231A1 EP 0210351 W EP0210351 W EP 0210351W WO 03029231 A1 WO03029231 A1 WO 03029231A1
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formula
compounds
methyl
alkyl
represents hydrogen
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PCT/EP2002/010351
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English (en)
Inventor
Yukiyoshi Watanabe
Koichi Ishikawa
Yuich Otsu
Katsuhiko Shibuya
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Bayer Cropscience Ag
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Publication of WO2003029231A1 publication Critical patent/WO2003029231A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole 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
    • C07D277/36—Sulfur 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
    • A01N43/72—Biocides, 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
    • A01N43/74—Biocides, 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 1,3
    • A01N43/78—1,3-Thiazoles; Hydrogenated 1,3-thiazoles

Definitions

  • the present invention relates to novel trifluorobutene derivatives, to processes for their preparation and to their use as nematicides.
  • U. S. Patent No. 3,513,172 describes trifluorobutenyl compounds with nematicidal activity.
  • Japanese Laid-open Patent Publication (PCT) No. 500037/1988 also refers to polyhaloalkene compounds with nematicidal activity.
  • WO95/24403 describes that 4,4-difluorobutenyl compounds have nematicidal activity.
  • R 1 represents hydrogen, halogen, alkyl, haloalkyl, cycloalkyl or alkoxycarbonyl- methyl
  • R 2 represents hydrogen, halogen, alkyl, alkoxyalkyl, alkylthioalkyl, carboxy, alkylaminocarbonyl, cycloalkylaminocarbonyl, dialkylaminocarbonyl or alkoxycarbonyl, and
  • n 0, 1 or 2
  • R and R do- not represent hydrogen at the same time, and in case R 1 represents hydrogen, then R 2 does not represent halogen.
  • the compounds of the above-mentioned formula (I) can be synthesized, for example, by the following preparation processes a), b) or c).
  • R 1 and R 2 have the aforementioned definitions
  • R . la represents alkyl
  • R ,2a represents hydrogen
  • the compounds of the formula (I) of the present invention show strong nematicidal activity and good compatibility with various crops. According to the present invention, the compounds of the formula (I) provide for an unexpectedly high nematicidal activity compared with the compounds described in the aforementioned prior art.
  • halogen represents fluoro, chloro, bromo or iodo, preferably represents fluoro, chloro or bromo, and particularly preferably represents chloro or bromo.
  • hydocarbon chains such as “alkyl” -also in connection with other moieties, such as “alkoxycarbonylmethyl”, “alkoxyalkyl”, “alkylthioalkyl”, “alkylaminocarbonyl”, “dialkylaminocarbonyl” or “alkoxycarbonyl”- are in each case straight-chain or branched-chain, such as methyl, ethyl, n- or iso-propyl, n-, iso-, sec- or tert-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl etc.
  • alkyl preferably represents Ci-s-alkyl, more preferably represents C ⁇ _ 6 -alkyl, and particularly preferably represents C ⁇ _ -alkyl.
  • haloalkyl represents “alkyl” substituted with at least one "halogen”, preferably represents C ⁇ - 4 -alkyl substituted with one or a plurality of halogen, and particularly preferably represents C ⁇ -alkyl substituted with one or a plurality of fluoro, chloro and/or bromo.
  • haloalkyl moieties are for example chloromethyl, bromomethyl, trifluoromethyl.
  • cycloalkylaminocarbonyl represents e.g. cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl etc.
  • Cycloalkyl preferably represents C 3 . 6 - cycloalkyl, and particularly preferably represents cyclopropyl, cyclopentyl or cyclohexyl.
  • the invention relates in each case to the R enantiomers and the S enantiomers and to any mixtures of these enantiomers, in particular to the racemates.
  • R 1 preferably represents hydrogen, fluoro, chloro, bromo, C ⁇ . 6 -alkyl or C ⁇ _ 3 -halo- alkyl, C 3 . 6 -cycloalkyl or C ⁇ ⁇ -alkoxycarbonylmethyl.
  • R 2 preferably represents hydrogen, fluoro, chloro, bromo, carboxy, C ⁇ - 6 -alkyl- C i _ 4 -alkoxy-C i . 4 -alkyl, C i _ 4 -alkylthio-C i ⁇ -alkyl, C i . 4 -alkylaminocarbonyl, C 3 . 6 cycloalkylaminocarbonyl, di-C ⁇ . 4 -alkylaminocarbonyl or C ⁇ -alkoxy- carbonyl.
  • n preferably represents 0 or 2.
  • R 1 particularly preferably represents hydrogen, fluoro, chloro, bromo, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, chloromethyl, bromomethyl, trifluoromethyl, cyclopropyl, cyclopentyl, cyclohexyl, methoxycarbonyl- methyl, ethoxycarbonylmethyl or n-propoxycarbonylmethyl.
  • R particularly preferably represents hydrogen, chloro, methyl, ethyl, methoxy- methyl, ethoxymethyl, methylthiomethyl, ethylthiomethyl, carboxy, methyl- aminocarbonyl, ethylaminocarbonyl, n-propylaminocarbonyl, isopropyl- aminocarbonyl, n-butylaminocarbonyl, sec-butylaminocarbonyl, cyclopropyl- aminocarbonyl, cyclopentylaminocarbonyl, cyclohexylaminocarbonyl, di- methylaminocarbonyl, diethylaminocarbonyl, methoxycarbonyl, ethoxy- carbonyl, n-propoxycarbonyl or isopropoxycarbonyl.
  • n particularly preferably represents 0.
  • R 1 represents hydrogen, fluoro, chloro, bromo, methyl, ethyl, n- or i-propyl or n-, i-, s-, or t-butyl, chloromethyl, bromomethyl, trifluoromethyl, cyclopropyl, cyclopentyl, cyclohexyl, methoxycarbonylmethyl, ethoxycarbonylmethyl, n- or i-propoxycarbonylmethyl,
  • R 2 represents hydrogen, fluoro, chloro, methyl, ethyl, n- or i-propyl, n-, i-, s-, or t-butyl, methoxymethyl, ethoxymethyl, methylthiomethyl, ethylthiomethyl, carboxy, methylaminocarbonyl, ethylaminocarbonyl, n- or i-propylamino- carbonyl, n-, i-, s-, or t-butylaminocarbonyl, cyclopropylaminocarbonyl, cyclopentylaminocarbonyl, cyclohexylaminocarbonyl, dimethylamino- carbonyl, diethylaminocarbonyl, methoxycarbonyl, ethoxycarbonyl or n- or i - propoxycarbonyl, and
  • n 0, 1 or 2
  • R ! and R 2 do not represent hydrogen at the same time, and in case R 1 represents hydrogen, then R 2 does not represent chloro.
  • the aforementioned preparation process a) for preparing a compound of the formula (I) of the present invention can be represented by the following reaction scheme when, for example, 5-ethoxycarbonyl-2-mercapto-4-methylthiazole and 4-bromo-
  • 1,1,2-trifluoro-l-butene are used as starting material.
  • the preparation process b for preparing a compound of the formula (I) of the present invention can be represented by the following reaction scheme when, for example, 5- ethoxycarbonyl-4-methyl-2-(3',4',4'-trifluoro-3'-butenylthio)thiazole is used as starting material and m-chloroperbenzoic acid is used as oxidizing agent.
  • the preparation process c for preparing a compound of the formula (I) of the present invention can be represented by the following reaction scheme when, for example, 4-methyl-2-(3 , ,4',4'-trifluoro-3'-butenylthio)thiazole is used as starting material and, for example, N-chlorosuccinimide is used as halogenating agent.
  • N-chlorosuccinimide is used as halogenating agent.
  • R and R have the aforementioned definition
  • ketones of the formula (III) used in the above-mentioned reaction can be prepared, for example, according to the process described in SHIN-JIKKEN KAGAKU KOUZA (New Lecture of Experimental Chemistry) 14 (1), 346-351, (1977) (published by MARUZEN).
  • 2-mercapto-4-trifluoromethylthiazole 2-mercapto-4-methylthiazole, 4-ethyl-2-mer- captothiazole, 4-cyclopropyl-2-mercaptothiazole, 5-diethylaminocarbonyl-2-mer- captothiazole, 5-isopropylaminocarbonyl-2-mercaptothiazole, 2-mercapto-5-meth- oxymethylthiazole, 2-mercapto-5-methylaminocarbonylthiazole, 5-cyclopropyl- aminocarbonyl-2-mercaptothiazole, 5-dimethylaminocarbonyl-2-mercaptothiazole, 5- diethylaminocarbonyl-2-mercaptothiazole, 2-mercapto-5-methylthiomethylthiazole, 2-mercapto-5-methoxycarbonyl-4-methylthiazole etc.
  • the compounds of the formula (la), used as starting material in the aforementioned preparation process b), correspond to the compounds of formula (I), wherein n represents 0. They can be synthesized, for example, according to the aforementioned preparation process a).
  • the oxidizing agents used for oxidation of a compound of the above-mentioned formula (la) in the preparation process b) are widely used in the field of organic chemistry.
  • Such compounds are, for example, hydrogen peroxide water, m- chloroperbenzoic acid, peracetic acid, perbenzoic acid, magnesium monoperoxy- phthalate, potassiumperoxymonosulfate etc.
  • the compounds of the formula (lb), used as starting material in the aforementioned preparation process c), are described by the compounds of the formula (I) wherein n represents 0. They can be synthesized, for example, according to the aforementioned preparation process a).
  • halogenating agents which are reacted with the compounds of the formula (lb) in the preparation process c) are widely used in the field of organic chemistry.
  • Such compound include, for example, sulfuryl chloride, N-chlorosuccinimide, N-bromo- succinimide, trichloroisocyanuric acid, potassium fluoride, chlorine gas, bromine, iodine etc.
  • the reaction of the preparation process a) can be conducted in the presence of an adequate diluent.
  • the following diluents can, for example, be used in the process: aliphatic, alicyclic and aromatic hydrocarbons, for example, hexane, cyclohexane, petroleum ether, ligroine, benzene, toluene, xylene etc.; ethers, for example, diethyl ether, methyl ethyl ether, di-isopropyl ether, dibutyl ether, propylene oxide, dioxane, tetrahydrofuran etc.; ketones, for example, acetone, methyl ethyl ketone, methyl isobutyl ketone etc.; nitriles, for example, acetonitrile, propionitrile, acrylonitrile etc.; acid amides, for example, dimethylformamide, dimethylacetamide, N-methyl-
  • the reaction of the preparation process (a) can be conducted in the presence of an acid binder.
  • the following acid binders can, for example, be used in the process: hydroxides, carbonates and alcoholates etc. of alkali metals, tertiary amines, for example, triethylamine, diethylaniline, pyridine, 4-dimethylaminopyridine, ,4- diazabicyclo[2,2,2]octane (DABCO), l,8-diazabicyclo[5,4,0]undec-7-ene (DBU) etc.
  • DBU diazabicyclo[2,2,2]octane
  • the reaction of the preparation process a) can be conducted in a substantially wide range of temperature.
  • the temperatures in a range of generally about 0°C to about 150°C, preferably about 20°C to about 100°C are especially suitable.
  • the reaction is desirably conducted under normal pressure, it can be optionally conducted under elevated pressure or under reduced pressure.
  • the compound of the corresponding formula (I) can be obtained, for example, by reacting 0.7-1.5 moles of 4-bromo-l,l,2- trifluoro-1-butene with 1 mole of the compound of the formula (II) in a diluent, for example, acetonitrile in the presence of 1-1.3 moles of a condensing agent, for example, potassium carbonate, under reflux by heating.
  • a condensing agent for example, potassium carbonate
  • the reaction of the preparation process b) can be conducted in the presence of an adequate diluent.
  • the following diluents can, for example, be used in the process: aliphatic, alicyclic and aromatic hydrocarbons (which may be optionally chlorinated), for example, hexane, cyclohexane, petroleum ether, ligroine, benzene, toluene, xylene, methylene chloride, chloroform, carbon tetrachloride, ethylene chloride, chlorobenzene etc.; ethers, for example, diethyl ether, methyl ethyl ether, di-isopropyl ether, dibutyl ether, dioxane, tetrahydrofuran etc.; alcohols, for example, methanol, ethanol, isopropanol, butanol, ethylene glycol etc.; esters, for example, ethyl acetate, amyl a
  • the reaction of the preparation process b) can be conducted in a substantially wide range of temperature.
  • the temperatures in a range of generally about -20°C to about 100°C, preferably about 0°C to about 80°C are especially suitable.
  • the reaction is desirably conducted under normal pressure, it can also be conducted under elevated pressure or under reduced pressure.
  • the compound of the corresponding formula (I) can be obtained, for example, by reacting, for example, 0.8-3 moles of m- chloroperbenzoic acid with 1 mole of the compound of the formula (la) in a diluent, for example, methylene chloride, at room temperature.
  • the reaction of the preparation process c) can be conducted in the presence of an adequate diluent.
  • the following diluents can, for example, be used in the process: aliphatic, alicyclic and aromatic hydrocarbons (which may be optionally chlorinated), for example, hexane, cyclohexane, petroleum ether, ligroine, benzene, toluene, xylene, methylene chloride, chloroform, carbon tetrachloride, ethylene chloride, chlorobenzene etc.; ethers, for example, diethyl ether, methyl ethyl ether, di-isopropyl ether, dibutyl ether, dioxane, tetrahydrofuran etc.; acid amides, for example, dimethylformamide, dimethylacetamide, N-methylpyrrolidone etc.; sulfones and sulfoxides, for example, dimethyl sulfox
  • the reaction of the preparation process c) can be conducted in a substantially wide range of temperature.
  • the temperatures in a range of generally about -20°C to about 200°C, preferably about 0°C to about 150°C are especially suitable.
  • reaction is desirably conducted under normal pressure, it can be optionally conducted under elevated pressure or under reduced pressure.
  • the compound of the corresponding formula (I) can be obtained, for example, by reacting 1-4 moles of N-chlorosuccinimide with 1 mole of the compound of the formula (lb) in a diluent, for example, carbon tetrachloride, under reflux by heating.
  • a diluent for example, carbon tetrachloride
  • the compounds of the formula (I) of the present invention display a strong controlling activity against nematodes. They can, therefore, be efficiently used as nematicidal agents, for example, in the field of agriculture and forestry. It is important to note that the compounds of the formula (I) of the present invention do not show phytotoxicity against crops while at the same time effectively controlling harmful nematodes.
  • the compounds according to the invention can be used, for example, against nema- todes such as Pratylenchus spp., Globodera spp., such as Globodera rostochiensis recycledweber, Heterodera spp., such as Heterodera glycines ichinohe, Meloidogyne spp., Aphelenchoides spp., such as Aphelenchoides basseyi christie, Radopholus similis, Ditylenchus dipsaci, Tylenchulus semipenetrans, Longidorus spp., Xiphinema spp., Trichodorus spp., Bursaphelenchus spp., such as Bursaphelenchus xylophilis etc.
  • nema- todes such as Pratylenchus spp., Globodera spp., such as Globodera rostochiensis recycledweber
  • the compounds according to the invention are especially useful for combating Pratylenchus spp., Globodera rostochiensis recycledweber, Heterodera glycines ichinohe, Meloidogyne spp., Aphelenchoides basseyi christie, Bursaphelenchus xylophilis.
  • the active compounds of the present invention can exist also as a mixed agent with other active compounds, for example, insecticides, bactericides, miticides, fungicides etc. in the form of their commercially useful formulation or in the application form prepared from tliose formulations.
  • insecticides there can be mentioned, for example, organophosphorous agents, carbamate agents, carboxylate type chemicals, chlorinated hydrocarbon type chemicals, chloronicotinyl type chemicals, insecticidal substances produced by microbes etc.
  • the active compounds according to the invention can also be used in a mixture with known fungicides, bactericides, acaricides, nematicides or insecticides, to widen, for example, the activity spectrum or to prevent the development of resistance. In many cases, this results in synergistic effects, i.e. the activity of the mixture exceeds the activity of the individual components.
  • Such formulations and application forms are commercially and ecologically especially useful as generally lower amounts of active ingredients can be used.
  • a synergist must not necessarily be active itself, as long as it enhances the action of the active compound.
  • the content of the active compounds of the present invention in a commercially useful formulation or application form can be varied in a wide range.
  • the active- compound content of the use forms prepared from the commercial formulations can vary within wide limits.
  • the active-compound concentration of the use forms can be from 0.0000001 to 100 % by weight of active compound, preferably between 0.0001 and 1 % by weight.
  • aldimorph ampropylfos, ampropylfos potassium, andoprim, anilazine, azaconazole, azoxystrobin, benalaxyl, benodanil, benomyl, benzamacril, benzamacril-isobutyl, bialaphos, binapacryl, biphenyl, bitertanol, blasticidin-S, bromuconazole, bupirimate, buthiobate, calcium polysulphide, capsimycin, captafol, captan, carbendazim, carboxin, carvon, quinomethionate, chlobenthiazone, chlorfenazole, chloroneb, chloropicrin, chlorothalonil, chlozolinate, clozylacon, cufraneb, cymoxanil, cyproconazole, cyprodinil, cyprofuram, debacarb
  • bronopol dichlorophen, nitrapyrin, nickel dimethyldithiocarbamate, kasugamycin, octhilinone, furancarboxylic acid, oxytetracyclin, probenazole, streptomycin, tecloftalam, copper sulphate and other copper preparations.
  • a mixture with other known active compounds, such as herbicides, or with fertilizers and growth regulators is also possible.
  • the active compounds can be converted into the customary formulations, such as solutions, emulsions, wettable powders, water dispersible granules, suspensions, powders, dusting agents, foaming agents, pastes, soluble powders, granules, suspo- emulsion concentrates, microcapsules, fumigants, natural and synthetic materials impregnated with active compound and very fine capsules and polymeric substances.
  • customary formulations such as solutions, emulsions, wettable powders, water dispersible granules, suspensions, powders, dusting agents, foaming agents, pastes, soluble powders, granules, suspo- emulsion concentrates, microcapsules, fumigants, natural and synthetic materials impregnated with active compound and very fine capsules and polymeric substances.
  • formulations can be prepared according to per se known methods, for example, by mixing the active compounds with extenders, namely liquid, liquefied gas or solid diluents or carriers, and optionally with surface-active agents, namely emulsifiers and/or dispersants and/or foam-forming agents.
  • extenders namely liquid, liquefied gas or solid diluents or carriers
  • surface-active agents namely emulsifiers and/or dispersants and/or foam-forming agents.
  • the extender used is water, it is also possible to use, for example, organic solvents as auxiliary solvents.
  • Suitable liquid solvents are essentially: aromatics, such as xylene, toluene, or alkylnaphthalenes, chlorinated aromatics and chlorinated aliphatic hydrocarbons, such as chlorobenzene, chloroethylenes or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, for example mineral oil fractions, mineral or vegetable oil, alcohols, such as butanol or glycol, and also their ethers and esters, ketones, such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents, such as dimethylformamide and dimethyl sulphoxide, and also water.
  • aromatics such as xylene, toluene, or alkylnaphthalenes
  • chlorinated aromatics and chlorinated aliphatic hydrocarbons such as chlorobenzene, chloroethylenes or methylene
  • Liquefied gas diluents or carriers are liquefied substances which are gases at normal temperature and pressure.
  • Liquefied gas diluents can be, for example, aerosol propel- lants such as butane, propane, nitrogen gas, carbon dioxide, halogenated hydrocarbons, etc.
  • Suitable solid carriers are, for example, ammonium salts and ground natural minerals, such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, ground synthetic minerals, such as finely divided silica, alumina and silicates;
  • suitable solid carriers for granules are, for example, crushed and fractionated natural rocks such as calcite, marble, pumice, sepiolite and dolomite, as well as synthetic granules of inorganic and organic meals, and granules of organic material such as sawdust, coconut shells, maize cobs and tobacco stalks;
  • suitable emulsif ⁇ ers and/or foam-formers are, for example, nonionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers such as alkylaryl polyglycol ethers, alkylsulphonates, alkyl sulphates, ary
  • Suitable tackifiers are, for example, carboxymethylcellulose and natural and synthetic polymers in the form of powders, granules or latices, such as gum arabic, polyvinyl alcohol and polyvinyl acetate, as well as natural phospholipids, such as cephalins and lecithins, and synthetic phospholipids, can be used in the formulations.
  • Other additives can be mineral and vegetable oils.
  • colorants such as inorganic pigments, for example iron oxide, titanium oxide and Prussian Blue, and organic dyestuffs, such as alizarin dyestuffs, azo dyestuffs and metal phthalocyanine dyestuffs, and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.
  • organic dyestuffs such as alizarin dyestuffs, azo dyestuffs and metal phthalocyanine dyestuffs
  • trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.
  • Said formulations can contain in a range of generally 0.1-95 % by weight, preferably 0.5-90 % by weight of the aforementioned active components.
  • test agent prepared as mentioned above was added to soil contaminated with Meloidogyne incognita to a chemical concentration of 10 ppm and homogeneously mixed by stirring.
  • a pot (1/5000 are) was filled with the soil.
  • About 20 seeds of tomato (variety: Kurihara) were sown per pot. After cultivation in a greenhouse for 4 weeks, they were carefully pulled out not to damage the roots and the root knot index and the controlling effect were determined as follows.
  • Root knot index x 100 Total number of tested individuals x 4
  • the controlling effect of the compounds tested can then be evaluated according to the following equation:

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  • Life Sciences & Earth Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Dentistry (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Plant Pathology (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Pest Control & Pesticides (AREA)
  • Agronomy & Crop Science (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Thiazole And Isothizaole Compounds (AREA)

Abstract

L'invention concerne de nouveaux dérivés de trifluorobutène représentés par la formule (I) dans laquelle R1 représente hydrogène, halogène, alkyle, haloalkyle, cycloalkyle ou alcoxycarbonylméthyle, R2 représente hydrogène, halogène, alkyle, alcoxyalkyle, alkylthioalkyle, carboxy, alkylaminocarbonyle, cycloalkylaminocarbonyle, dialkylaminocarbonyle ou alcoxycarbonyle, et n représente 0, 1 ou 2, à condition que R1 et R2 ne représentent pas hydrogène en même temps, et que dans le cas où R1 représente hydrogène, alors R2 ne représente pas halogène. L'invention concerne également un procédé de préparation de ces dérivés ainsi que leur utilisation en tant que nématicides.
PCT/EP2002/010351 2001-09-28 2002-09-16 Derives de trifluorobutene nematicide WO2003029231A1 (fr)

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JP2001-301316 2001-09-28
JP2001301316A JP2003113168A (ja) 2001-09-28 2001-09-28 殺センチュウ性トリフルオロブテン誘導体

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Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2003106436A1 (fr) * 2002-06-14 2003-12-24 Bayer Cropscience Ag Trifluorobutenes nematicides contenant du tetrazole
WO2004095929A1 (fr) * 2003-05-02 2004-11-11 Bayer Cropscience Aktiengesellschaft Combinaisons de matiere active a proprietes nematicides, insecticides et fongicides, a base de composes de trifluorobutenyle
WO2004095930A1 (fr) * 2003-05-02 2004-11-11 Bayer Cropscience Aktiengesellschaft Associations de substances actives presentant des proprietes nematicides et insecticides, a base de composes trifluorobutenyle
DE102007012168A1 (de) 2007-03-12 2008-09-18 Bayer Cropscience Ag 2-[Heteroarylalkyl-sulfonyl]-thiazol-Derivate und 2-[Heteroarylalkyl-sulfinyl]-thiazol-Derivate, Verfahren zu deren Herstellung, sowie deren Verwendung als Herbizide und Pflanzenwachstumsregulatoren
WO2013104171A1 (fr) * 2012-01-10 2013-07-18 山东省联合农药工业有限公司 Pesticide à base de trifluorobutène contenant du thiazole
WO2019123196A1 (fr) 2017-12-20 2019-06-27 Pi Industries Ltd. Composés fluoroalcényles, procédé pour leur préparation et leur utilisation
WO2020095161A1 (fr) 2018-11-05 2020-05-14 Pi Industries Ltd. Composés nitrones et leur utilisation
CN111885917A (zh) * 2018-01-23 2020-11-03 安道麦马克西姆有限公司 5-氯-2-[(3,4,4-三氟-3-丁烯-l-基)硫代]-噻唑的合成

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AR116506A1 (es) * 2018-09-26 2021-05-12 Adama Makhteshim Ltd Proceso e intermediarios para la preparación de fluensulfona
WO2020141514A1 (fr) * 2018-12-31 2020-07-09 Adama Makhteshim Ltd. Synthèse de 1,1,2-trifluoro-4-(sufonyl substitué)-but-1-ène

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WO2003106436A1 (fr) * 2002-06-14 2003-12-24 Bayer Cropscience Ag Trifluorobutenes nematicides contenant du tetrazole
US9072300B2 (en) 2003-05-02 2015-07-07 Adama Makhteshim Ltd. Active substance combinations that have nematicidal, insecticidal, and fungicidal properties and are based on trifluorobutenyl compounds
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CN102550570B (zh) * 2003-05-02 2015-07-08 马克特辛姆化学工厂有限公司 基于三氟丁烯基化合物的、具有杀线虫、杀昆虫及杀真菌特性的活性物质的结合物
KR100914413B1 (ko) * 2003-05-02 2009-08-31 바이엘 크롭사이언스 아게 트리플루오로부티닐 화합물에 기초한 살선충 및 살충성활성 물질 배합물
CN105104414A (zh) * 2003-05-02 2015-12-02 阿达玛马克西姆有限公司 基于三氟丁烯基化合物的、具有杀线虫、杀昆虫及杀真菌特性的活性物质的结合物
AU2004233566B2 (en) * 2003-05-02 2010-01-14 Makhteshim Chemical Works Ltd. Active substance combination based on trifluorobutinyl compounds and exhibiting nematicidal and insecticidal properties
CN101720782A (zh) * 2003-05-02 2010-06-09 马克特辛姆化学工厂有限公司 基于三氟丁烯基化合物的、并表现出杀线虫及杀昆虫特性的活性物质的结合物
US9642366B2 (en) 2003-05-02 2017-05-09 Adama Makhteshim Ltd. Active substance combinations that have nematicidal, insecticidal, and fungicidal properties and are based on trifluorobutenyl compounds
US8426605B2 (en) 2003-05-02 2013-04-23 Makhteshim Chemical Works, Ltd. Active substance combinations that have nematicidal, insecticidal, and fungicidal properties and are based on trifluorobutenyl compounds
US11026425B2 (en) 2003-05-02 2021-06-08 Adama Makhteshim Ltd. Active substance combinations that have nematicidal, insecticidal, and fungicidal properties and are based on trifluorobutenyl compounds
US8815921B2 (en) 2003-05-02 2014-08-26 Makhteshim Chemical Works, Ltd. Active substance combination based on trifluorobutinyl compounds and exhibiting nematicidal and insecticidal properties
WO2004095929A1 (fr) * 2003-05-02 2004-11-11 Bayer Cropscience Aktiengesellschaft Combinaisons de matiere active a proprietes nematicides, insecticides et fongicides, a base de composes de trifluorobutenyle
US10412966B2 (en) 2003-05-02 2019-09-17 Adama Makhteshim Ltd. Active substance combinations that have nematicidal, insecticidal, and fungicidal properties and are based on trifluorobutenyl compounds
WO2004095930A1 (fr) * 2003-05-02 2004-11-11 Bayer Cropscience Aktiengesellschaft Associations de substances actives presentant des proprietes nematicides et insecticides, a base de composes trifluorobutenyle
CN101843248B (zh) * 2003-05-02 2012-01-11 马克特辛姆化学工厂有限公司 基于三氟丁烯基化合物的、具有杀线虫、杀昆虫及杀真菌特性的活性物质的结合物
US9681662B2 (en) 2003-05-02 2017-06-20 Adama Makhteshim Ltd. Active substance combination based on trifluorobutinyl compounds and exhibiting nematicidal and insecticidal properties
CN105165845B (zh) * 2003-05-02 2018-06-12 阿达玛马克西姆有限公司 基于三氟丁烯基化合物的、并表现出杀线虫及杀昆虫特性的活性物质的结合物
US10045535B2 (en) 2003-05-02 2018-08-14 Adama Makhteshim Ltd. Active substance combination based on trifluorobutinyl compounds and exhibiting nematicidal and insecticidal properties
DE102007012168A1 (de) 2007-03-12 2008-09-18 Bayer Cropscience Ag 2-[Heteroarylalkyl-sulfonyl]-thiazol-Derivate und 2-[Heteroarylalkyl-sulfinyl]-thiazol-Derivate, Verfahren zu deren Herstellung, sowie deren Verwendung als Herbizide und Pflanzenwachstumsregulatoren
WO2013104171A1 (fr) * 2012-01-10 2013-07-18 山东省联合农药工业有限公司 Pesticide à base de trifluorobutène contenant du thiazole
WO2019123196A1 (fr) 2017-12-20 2019-06-27 Pi Industries Ltd. Composés fluoroalcényles, procédé pour leur préparation et leur utilisation
CN111670180A (zh) * 2017-12-20 2020-09-15 Pi工业有限公司 氟烯基化合物，制备方法及其用途
CN111885917A (zh) * 2018-01-23 2020-11-03 安道麦马克西姆有限公司 5-氯-2-[(3,4,4-三氟-3-丁烯-l-基)硫代]-噻唑的合成
CN111885917B (zh) * 2018-01-23 2023-07-28 安道麦马克西姆有限公司 5-氯-2-[(3,4,4-三氟-3-丁烯-l-基)硫代]-噻唑的合成
WO2020095161A1 (fr) 2018-11-05 2020-05-14 Pi Industries Ltd. Composés nitrones et leur utilisation

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