WO1995000499A1 - 1,5-diaryl-1h-1,2,4-triazol-3-carboxamides substitues herbicides - Google Patents

1,5-diaryl-1h-1,2,4-triazol-3-carboxamides substitues herbicides Download PDF

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Publication number
WO1995000499A1
WO1995000499A1 PCT/EP1994/001829 EP9401829W WO9500499A1 WO 1995000499 A1 WO1995000499 A1 WO 1995000499A1 EP 9401829 W EP9401829 W EP 9401829W WO 9500499 A1 WO9500499 A1 WO 9500499A1
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stands
radical
substituted
alkyl
series
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PCT/EP1994/001829
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German (de)
English (en)
Inventor
Thomas Bretschneider
Peter Andres
Norbert Lui
Markus Dollinger
Hans-Joachim Santel
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Bayer Aktiengesellschaft
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Priority to AU71229/94A priority Critical patent/AU7122994A/en
Publication of WO1995000499A1 publication Critical patent/WO1995000499A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles 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
    • A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
    • A01N43/647—Triazoles; Hydrogenated triazoles
    • A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
    • C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
    • C07D263/30—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D263/34—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole 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
    • C07D263/48—Nitrogen atoms not forming part of a nitro radical

Definitions

  • the invention relates to new substituted 1,5-diaryl-1H-1,2,4-triazole-3-carboxamides, several processes their manufacture and their use as herbicides.
  • 1,5-Diaryl-1H-1,2,4-triazole-3-carboxamides with fluorine and / or chlorine-substituted alkenyl, cycloalkyl or cycloalkenyl radicals in an alkoxymethylene side chain of 1,5-diaryl-1H- 1,2,4-triazole-3-carboxamide ring systems.
  • R represents a radical of the series alkenyl, cycloalkyl or cycloalkenyl substituted with fluorine and / or chlorine and optionally with alkyl.
  • p stands for a number between 0 and 2
  • X for hydrogen, halogen, carboxy, nitro, cyano or for a straight-chain or branched and optionally substituted radical of the alkyl series.
  • Y represents hydrogen, halogen, carboxy, nitro, cyano, or a straight-chain or branched and optionally substituted radical of the alkyl, alkoxy, alkylcarbonyl, alkoxycarbonyl, alkylthio, alkylsulfinyl or Alkylsulfonyl
  • n stands for a number between 0 and 5
  • m stands for a number between 0 and 4, found.
  • the compounds of the formula (I) can also contain one or more centers of chirality and can thus be present in different mixtures of enantiomers and diastereomers, which can optionally be separated in a customary manner. Both the pure enantiomers and diastereomers and the mixtures are claimed according to the invention
  • R represents a radical of the series alkenyl, cycloalkyl or cycloalkenyl substituted with fluorine and / or chlorine and optionally with alkyl
  • p stands for a number between 0 and 2
  • X represents hydrogen, halogen, carboxy, nitro, cyano or a straight-chain or branched and optionally substituted radical from the series alkyl, alkoxy, alkylcarbonyl, alkoxycarbonyl, alkylthio.
  • Y represents hydrogen, halogen, carboxy, nitro, cyano or a straight-chain or branched and optionally substituted radical in the series Alkyl, alkoxy, alkylcarbonyl, alkoxycarbonyl, alkylthio.
  • R represents a radical of the series C 2-8 alkenyl, C 3-8 cycloalkyl or C 4-8 cycloalkenyl which is substituted by fluorine and / or chlorine and optionally substituted by C 1 -2 alkyl
  • p represents a number between 0 and 2 stands
  • X is hydrogen, fluorine, chlorine, bromine, iodine, nitro, cyano, carboxy, or for an in each case linear or branched radical from the series C 1 -8 alkyl, C1 -8 - haloalkyl, C 1 -8 alkoxy, C 1- 8 -haloalkoxy, C 1 -8 -alkylcarbonyl, C 1 -8 -alkoxycarbonyl, C 1 -8- alkylthio, C 1 -8 -alkylsulfinyl or C 1 -8 -alkylsulfonyl,
  • Y for hydrogen fluorine, chlorine, bromine, iodine, nitro, cyano, carboxy or for a straight-chain or branched radical of the series C 1-8 -alkyl, C 1-8 - haloalkyl, C 1-8 -alkoxy, C 1 - 8 -haloalkoxy, C 1 -8 -alkylcarbonyl, C 1-8 -alkoxycarbonyl, C 1-8 -alkylthio, C 1 -8 -alkylsulfmyl or C 1 -8 -alkylsulfonyl, n stands for a number between 0 and 5 and m stands for a number between 0 and 4.
  • R represents a radical of the series C 2-8 alkenyl, C 3-6 cycloalkyl or C 4-6 cycloalkenyl which is substituted by fluorine and / or chlorine and optionally substituted by C 1-2 alkyl, p stands for a number between 0 and 1,
  • X represents hydrogen, fluorine, chlorine, bromine, iodine, nitro, cyano, carboxy or for a straight-chain or branched radical from the series C 1 -4 -alkyl, C 1 -4 -haloalkyl, C 1 -4 -alkoxy, C 1 -4 -haloalkoxy, C 1 -4 -alkylcarbonyl, C 1 -4 -alkoxycarbonyl, C 1 -4 -alkylthio, C 1 -4 -alkylsulfinyl or C 1 -4 -alkylsulfonyl.
  • Y for hydrogen fluorine, chlorine, bromine, iodine, nitro, cyano, carboxy, for a straight-chain or branched radical of the series C 1 -4 - alkyl, C 1 -4 - haloalkyl, C 1 -4 - alkoxy, C 1 - 4 -haloalkoxy, C 1 - 4 - alkylcarbonyl, C 1 -4 - alkoxycarbonyl, C 1 -4 - alkylthio, C 1 -4 - alkylsulfinyl or C 1 -4 alkylsulphonyl.
  • n stands for a number between 0 and 3 and m stands for a number between 0 and 3.
  • R represents a radical of the series ethenyl, propenyl, butenyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclobutenyl, cyclopentenyl or cyclohexenyl which is substituted by fluorine and / or chlorine and optionally methyl
  • p stands for a number between 0 and 1
  • X for hydrogen, fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, pentafluoroethyl, n-propyl, i-propyl, methoxy, ethoxy, chloromethyl, difluoromethyl.
  • Trifluoromethyl trifluoromethoxy, acetyl, methoxycarbonyl, ethoxy carbonyl, carboxy, cyano, nitro, methylthio, ethylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl, ethylsulfonyl,
  • Y for hydrogen, fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl
  • Ethylsulfinyl, methylsulfonyl, ethylsulfonyl, n stands for a number between 0 and 2 and m stands for a number between 0 and 2.
  • 1- (3-chloromethyl-4-chlorophenyl) -5-phenyl-1H-1,2 is used , 4-triazoI-3-carboxamide and 2-chloro-2,3,3-trifluorocyclobutanol as starting materials
  • the course of the reaction of process (a) according to the invention can be represented by the following formula:
  • the 1,5-diaryl-1H-1,2,4-triazole-3-carboxamides required as starting materials for carrying out process (a) according to the invention are represented by the formula (II) generally defined.
  • X, Y, m and n preferably and particularly preferably represent those radicals which have already been mentioned as preferred and particularly preferred for these substituents in connection with the description of the compounds of the formula (I) according to the invention.
  • Hal stands for halogen or for another leaving group, preferably for fluorine, chlorine, bom, iodine, tosylate, mesylate or triflate. particularly preferred for chlorine, tosylate, mesylate or triflate.
  • Formula (III) provides a general definition of the alcohol derivatives which are further required as starting materials for carrying out process (a) according to the invention.
  • R and p preferably and particularly preferably represent those radicals which have already been mentioned as preferred and particularly preferred for these substituents in connection with the description of the compounds of the formula (I) according to the invention.
  • Formula (IV) provides a general definition of the 1,5-diaryl-1H-1,2,4-triazole-3-carboxamides required as starting materials for carrying out process (b) according to the invention.
  • X, Y, m and n preferably and particularly preferably represent those radicals which have already been mentioned as preferred and particularly preferred for these substituents in connection with the description of the substances of the formula (I) according to the invention.
  • the 1,5-diaryl-1H-1,2,4-triazole-3-carboxamides of the formula (IV) are known or can be obtained in analogy to known processes as described in the above-mentioned patents.
  • the derivatives of the formula (V) which are furthermore required as starting materials for carrying out the process (b) according to the invention are generally defined by the formula (V).
  • p and R preferably represent those radicals which have already been mentioned as preferred and particularly preferred for these substituents in connection with the description of the substances of the formula (I) according to the invention.
  • Hal represents halogen or another leaving group, preferably fluorine, chlorine, bromine, iodine, tosylate, mesylate or triflate, particularly preferably chlorine, tosylate, mesylate or triflate
  • the derivatives of the formula (V) are generally known compounds of organic chemistry. Their syntheses are also described in the publications mentioned for the synthesis of the alcohol derivatives of the formula (III).
  • Formula (VI) provides a general definition of the substituted 2-aryl-4- (arylhydrazono) -2-oxazolin-5-ones required as starting materials for carrying out process (c) according to the invention.
  • R, X, Y, p, n and m preferably and particularly preferably for those radicals which have already been mentioned as preferred and particularly preferred for these substituents in connection with the description of the substances of the formula (I) according to the invention.
  • the 2-aryl-4- (arylhydrazono) -2-oxazolin-5-ones of the formula (VI) are compounds according to the invention. They are obtained via the substituted nitrobenzene derivatives (IX), either by reaction of the benzyl alcohols (VII) with halides of the Type (III) or by reaction of the benzyl halides (VIII) with alcohols of the type (V) are accessible. The reduction of these nitrobenzenes gives the aniline derivatives (X), which are converted to the derivatives (VI) by diazotization and reaction with 2-aryloxazolin-5-ones (XI) (Scheme 1).
  • Process (a) according to the invention for the preparation of the new substituted 1,5-diaryl-1H-1,2,4-triazole-3-carboxamides of the general formula (I) is preferably carried out using a diluent
  • Inert organic solvents are suitable as diluents for carrying out process (a) according to the invention.
  • These include in particular aliphatic, alicyclic or aromatic, optionally halogenated hydrocarbons, such as, for example, gasoline, benzene, toluene, xylene, chlorobenzene, dichlorobenzene, petroleum ether, hexane, cyclohexane, dichloromethane. Chloroform or carbon tetrachloride; Ethers, such as diethyl ether, diisopropyl ether, dioxane. Tetrahydrofuran or ethylene glycol dimethyl or diethyl ether; Ketones such as acetone.
  • Butanone or methyl isobutyl ketone Nitriles such as acetonitrile, propionitrile or benzonitrile; Amides such as N, N-dimethylformamide. N, N-dimethylacetamide, N-methylformanilide, N-methylpyrrolidone or hexamethylphosphoric triamide or esters, such as methyl acetate or ethyl acetate.
  • Process (a) according to the invention is preferably carried out in the presence of a suitable reaction auxiliary.
  • a suitable reaction auxiliary As such come all the usual inorganic or organic bases. These include, for example, alkaline earth or alkali metal hydroxides. such as sodium hydroxide, calcium hydroxide, potassium hydroxide or ammonium hydroxide also, alkaline earth metal or alkali metal hydrides such as sodium hydride, potassium hydride, alkali metal carbonates such as sodium carbonate, potassium carbonate, potassium hydrogen carbonate, sodium hydrogen carbonate or ammonium carbonate, alkali metal or alkaline earth metal acetates such as sodium acetate, potassium acetate, calcium acetate or ammonium acetate, and also tertiary amines such as trimethylamine, triethylamine, tributylamine, N, N-dimethylaniline, pyridine, piperidine, N-methylpiperidine, N, N-dimethylaminopyridine, diaza
  • reaction temperatures can be varied within a substantial range when carrying out process (a) according to the invention. Generally one works at temperatures between -80 ° C and + 180 ° C, preferably at temperatures between -20 ° C and + 120 ° C.
  • Process (a) according to the invention is usually carried out under normal pressure. However, it is also possible to work under increased or reduced pressure.
  • 1.0 to 5.0 mol, preferably 1.0 to 2.0 mol, of alcohol derivative of the formula (III) and, if appropriate, 1.0 to 5.0 mol are generally employed per mol of triazole of the formula (II) 5.0 mol, preferably 1.0 to 2.0 mol, of base as reaction auxiliary.
  • the reaction products are worked up and isolated using generally known organic chemical processes (cf. the preparation examples).
  • Inert organic solvents are suitable as diluents for carrying out process (b) according to the invention.
  • the solvents listed in the description of the implementation of process (a) according to the invention are preferably used.
  • Process (b) according to the invention is preferably carried out in the presence of a suitable reaction auxiliary.
  • a suitable reaction auxiliary All conventional inorganic or organic bases are suitable as such. These include, for example, alkaline earth or Alkali metal hydrides, hydroxides, amides, alcoholates, acetates, carbonates or hydrogen carbonates, such as, for example, sodium hydride, sodium amide, sodium methylate, sodium ethylate, potassium tert.-butylaf sodium hydroxide, potassium hydroxide.
  • Ammonium hydroxide sodium acetate, potassium acetate, calcium acetate, ammonium acetate, sodium carbonate, potassium carbonate, potassium hydrogen carbonate, sodium hydrogen carbonate or ammonium carbonate and also tertiary amines, such as trimethylamine, triethylamine, tributylamine, N, N-dimethylaniline, pyridine, N-methylpiperidine, N, N-dimethylaminopyridine, N, N-dimethylaminopyridine, DABCO), diazabicyclonones (DBN) or diazabicycloundecene (DBU).
  • the reaction temperatures can be varied within a substantial range when carrying out process (b) according to the invention. In general, temperatures between -80 ° C and + 150 ° C, preferably at temperatures between -20 ° C and + 120 ° C.
  • Process (b) according to the invention is usually carried out under normal pressure. However, it is also possible to work under increased or reduced pressure.
  • 1.0 to 5.0 mol, preferably 1.0 to 2.0 mol, of the derivative of the formula (V) and generally 1, are generally employed per mol of triazole of the formula (IV), 0 to 5.0 mol, preferably 1.0 to 2.0 mol, of base as a reaction auxiliary.
  • reaction is carried out, worked up and isolated using generally customary, known processes (see also the preparation examples).
  • Process (c) according to the invention is usually carried out using a diluent.
  • Inert organic solvents are suitable as diluents for carrying out process (c) according to the invention.
  • These include in particular aliphatic, alicyclic or aromatic, optionally halogenated hydrocarbons, such as, for example, gasoline, benzene, toluene, xylene, chlorobenzene, dichlorobenzene, Petroleum ether, hexane, cyclohexane, dichloromethane, chloroform, carbon tetrachloride; Ethers such as diethyl ether, diisopropyl ether, dioxane, tetrahydrofuran or ethylene glycol dimethyl or diethyl ether; Ketones such as acetone, butanone or methyl isobutyl ketone; Nitriles such as acetonitrile, propionitrile or benzonitrile; Amides such as N, N-dimethylformamide, N, N-dimethylacetamide, N-methyl
  • reaction temperatures can be varied within a substantial range when carrying out process (c) according to the invention.
  • temperatures between -20oC and + 150oC. preferably at temperatures between 0 ° C and + 120 ° C.
  • Process (c) according to the invention is usually carried out under normal pressure. However, it is also possible to work under increased or reduced pressure.
  • a large excess of 1 to 100 mol of ammonia is generally employed per mole of oxazolinone of the formula (VI).
  • the reaction products are worked up and isolated in analogy to generally known methods of organic chemistry (cf. the preparation examples).
  • the end products of the formula (I) are purified using customary methods, for example by column chromatography or by recrystallization.
  • the characterization is carried out using the melting point or, in the case of non-crystallizing compounds, using proton nuclear magnetic resonance spectroscopy ( 1 H-NMR).
  • the active compounds according to the invention can be used as defoliants, desiccants, haulm killers and in particular as weed killers. Weeds in the broadest sense are to be understood as all plants which grow up in places where they are undesirable. Whether the substances according to the invention act as total or selective herbicides depends essentially on the amount used.
  • the active compounds according to the invention can be used, for example, in the following plants:
  • the use of the active compounds according to the invention is by no means restricted to these genera, but extends in the same way to other plants.
  • the compounds are suitable for total weed control, e.g. on industrial and track systems and on paths and squares with and without tree cover.
  • the compounds for weed control in permanent crops e.g. Forests, ornamental trees, fruit, wine, citrus, nut, banana, coffee, tea, rubber, oil palm, cocoa, berry fruit and hop plants and for selective weed control in annual crops.
  • the active compounds according to the invention can be used particularly successfully to control dicotyledon weeds.
  • the active ingredients can be converted into the customary formulations, such as solutions, emulsions, suspensions, powders, foams, pastes, granules, aerosols, active ingredient-impregnated natural and synthetic substances, very fine encapsulations in polymers Fabrics and in coating compositions for seeds, also in formulations with fuel sets, such as smoking cartridges, cans, spirals, etc., and ULV cold and warm mist formulations.
  • formulations are prepared in a known manner, for example by mixing the active ingredients with extenders, that is to say liquid solvents, pressurized liquefied gases and / or solid carriers, optionally using surface-active agents, that is to say emulsifiers and / or dispersants and / or foam-generating agents. If water is used as an extender, organic solvents can, for example, also be used as auxiliary solvents.
  • extenders that is to say liquid solvents, pressurized liquefied gases and / or solid carriers, optionally using surface-active agents, that is to say emulsifiers and / or dispersants and / or foam-generating agents.
  • surface-active agents that is to say emulsifiers and / or dispersants and / or foam-generating agents.
  • organic solvents can, for example, also be used as auxiliary solvents.
  • liquid solvents aromatics, such as xylene, toluene or alkylnaphthalenes, chlorinated aromatics or chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chlorethylenes or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, for example petroleum fractions, alcohols, such as butanol or glycol, and the like Ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as dimethylformamide and dimethyl sulfoxide, as well as water: with liquefied gaseous extenders or carriers are meant such liquids which are gaseous at normal temperature and under normal pressure, e.g.
  • aerosol -Fuel gases such as halogenated hydrocarbons and butane, propane.
  • Nitrogen and carbon dioxide Solid carriers are possible: for example natural rock powder, such as kaolins, clays, talc, chalk, quartz, attapulgite montmorillonite or diatomaceous earth and synthetic rock powder, such as highly disperse silica, aluminum oxide and silicates; Solid carriers for granules are possible: for example broken and fractionated natural rocks such as calcite, marble, pumice, sepiolite, dolomite and synthetic granules from inorganic and organic flours as well as granules from organic material such as sawdust, coconut shells, corn cobs and tobacco stalks; suitable emulsifiers and / or foam-generating agents are: for example nonionic and anionic emulsifiers, such as polyoxyethyl Len fatty acid esters, polyoxyethylene fatty alcohol ethers, e.g.
  • alkylaryl polyglycol ether alkyl sulfonates, alkyl sulfates, aryl sulfonates and protein hydrolyzates: as dispersants there are possible: e.g. lignin sulfite waste liquors and methyl cellulose.
  • Adhesives such as carboxymethyl cellulose, natural and synthetic polymers in the form of powders, granules or latices, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, and natural phospholipids, such as cephalins and lecithins, and synthetic phospholipids can be used in the formulations.
  • Other additives can be mineral and vegetable oils.
  • Dyes such as inorganic pigments, e.g. Iron oxide, titanium oxide. Ferrocyan blue and organic dyes such as alizarin. Azo and metal phthalocyanine dyes and trace nutrients such as salts of iron. Manganese, boron, copper, cobalt, molybdenum and tin can be used.
  • the formulations generally contain between 0.1 and 95 percent by weight of active compound, preferably between 0.5 and 90%.
  • the active compounds according to the invention can also be used for combating weeds, in a mixture with known herbicides, finished formulations or tank mixes being possible.
  • herbicides are suitable for the mixtures, for example anilides, such as, for example, diflufenican and propanil; Aryl carboxylic acids, such as dichloropicolinic acid, dicamba or picloram; Aryloxyalkanoic acids.
  • Aryloxy-phenoxy-alkanoic acid esters such as, for example, diclofop-methyl, fenoxaprop-ethyl, ruazifop-butyl, haloxyfop-methyl and quizalofopethyl;
  • Azinones such as chloridazon and norflurazon;
  • Carbamates such as chlorpropham, desmedipham, phenmedipham and propham;
  • Chloroacetanilides such as alachlor, acetochlor, butachlor, metazachlor, metolachlor, pretilachlor and propachlor; Dinitroanilines such as oryzalin, pendimethalin and trifluralin; Diphenyl ethers such as acifluorfen, bifenox, fluoroglycofen, fomesafen, halosafen, lac
  • a mixture with other known active compounds such as fungicides, insecticides, acaricides, nematicides, bird repellants, plant nutrients and agents which improve soil structure, is also possible.
  • the active ingredients as such, in the form of their formulations or the use forms prepared therefrom by further dilution, such as ready-to-use solutions.
  • Suspensions, emulsions, powders, pastes and granules can be used. They are used in the usual way, e.g. by pouring, spraying; Spray, sprinkle.
  • the active compounds according to the invention can be applied both before and after emergence of the plants. They can also be worked into the soil before sowing.
  • the amount of active ingredient used can vary over a wide range. It essentially depends on the type of effect desired. In general, the application rates are between 0.01 and 10 kg of active ingredient per hectare of soil, preferably between 0.05 and 5 kg per hectare.
  • reaction mixture is stirred into 1.21 water, the product is extracted several times with methyl tert-butyl ether, the organic phase is washed with water, dried and concentrated in vacuo. Further purification is carried out by column chromatography on silica gel with cyclohexane / ethyl acetate 5: 1 as the eluent. Yield: 20.7 g (66% of theory) of 4-chloro-3- (2,2,3,3-tetrafluorocyclobutyloxymethyl) nitrobenzene, mp. 35-50 ° C.
  • the catalyst is filtered off through Celite, the filtrate is concentrated in vacuo, the residue is partitioned between methylene chloride and water, the organic phase is washed with sodium bicarbonate solution and sodium chloride solution, dried and concentrated in vacuo. Further purification is carried out by bulb tube distillation in a high vacuum.
  • Example 5 (Method a, Example No. 40)
  • Emulsifier 1 part by weight of alkylaryl polyglycol ether To prepare a suitable preparation of active compound, mix 1 part by weight of active compound with the stated amount of solvent, add the stated amount of emulsifier and dilute the concentrate with water to the desired concentration.
  • Seeds of the test plants are sown in normal soil and watered with the active compound preparation after 24 hours.
  • the amount of water per unit area is expediently kept constant.
  • the concentration of active substance in the preparation is irrelevant, the only decisive factor is the amount of active substance applied per unit of area.
  • the degree of damage to the plants is rated in% damage compared to the development of the untreated control. It means:
  • Emulsifier 1 part by weight of alkylaryl polyglycol ether To prepare a suitable preparation of active compound, mix 1 part by weight of active compound with the stated amount of solvent, add the stated amount of emulsifier and dilute the concentrate with water to the desired concentration.
  • the active ingredient preparation is used to inject test plants which have a height of 5 to 15 cm. that the desired amounts of active ingredient are applied per unit area. After three weeks, the degree of damage to the plants is rated in% damage compared to the development of the untreated control. It means:

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  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth 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)
  • Plural Heterocyclic Compounds (AREA)

Abstract

De nouveaux 1,5-diaryl-1H-1,2,4-triazol-3-carboxamides substitués répondent à la formule générale (I), dans laquelle R désigne un reste de la série alcényle, cycloalkyle ou cycloalcényle, substitué par fluor et/ou chlore et, le cas échéant, par alkyle. L'invention concerne également leur préparation, leur utilisation comme herbicides et des dérivés correspondants de 2-aryl-4-(arylhydrazono)-2-oxazolin-5-one.
PCT/EP1994/001829 1993-06-17 1994-06-06 1,5-diaryl-1h-1,2,4-triazol-3-carboxamides substitues herbicides WO1995000499A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU71229/94A AU7122994A (en) 1993-06-17 1994-06-06 Herbicidal substituted 1,5-diaryl-1h-1,2,4-triazol-3-carboxamides

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DE19934320076 DE4320076A1 (de) 1993-06-17 1993-06-17 Substituierte 1,5-Diaryl-1H-1,2,4-triazol-3-carboxamide
DEP4320076.1 1993-06-17

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WO1995000499A1 true WO1995000499A1 (fr) 1995-01-05

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN114456121A (zh) * 2022-02-24 2022-05-10 安徽大学 一种1,2,4-三氮唑衍生物的合成方法

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0220956A2 (fr) * 1985-10-25 1987-05-06 Kureha Kagaku Kogyo Kabushiki Kaisha 1,2,4-Triazole-3-carboxamides herbicides
EP0282303A1 (fr) * 1987-03-10 1988-09-14 Kureha Kagaku Kogyo Kabushiki Kaisha Dérivés du diphényl-1,5-1H-triazole-1,2,4 carboxamide-3 et compositions herbicides les contenant
EP0282669A1 (fr) * 1987-03-19 1988-09-21 Kureha Kagaku Kogyo Kabushiki Kaisha Dérivés herbicides du 1,5-diphényl-1H-1,2,4-triazole-3-carboxamide

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0220956A2 (fr) * 1985-10-25 1987-05-06 Kureha Kagaku Kogyo Kabushiki Kaisha 1,2,4-Triazole-3-carboxamides herbicides
EP0282303A1 (fr) * 1987-03-10 1988-09-14 Kureha Kagaku Kogyo Kabushiki Kaisha Dérivés du diphényl-1,5-1H-triazole-1,2,4 carboxamide-3 et compositions herbicides les contenant
EP0282669A1 (fr) * 1987-03-19 1988-09-21 Kureha Kagaku Kogyo Kabushiki Kaisha Dérivés herbicides du 1,5-diphényl-1H-1,2,4-triazole-3-carboxamide

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN114456121A (zh) * 2022-02-24 2022-05-10 安徽大学 一种1,2,4-三氮唑衍生物的合成方法
CN114456121B (zh) * 2022-02-24 2024-04-12 安徽大学 一种1,2,4-三氮唑衍生物的合成方法

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AU7122994A (en) 1995-01-17

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