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EP0983261A1 - Pyridylpyrazoles substitues comme herbicides, insecticides et acaricides - Google Patents

Pyridylpyrazoles substitues comme herbicides, insecticides et acaricides

Info

Publication number
EP0983261A1
EP0983261A1 EP98928227A EP98928227A EP0983261A1 EP 0983261 A1 EP0983261 A1 EP 0983261A1 EP 98928227 A EP98928227 A EP 98928227A EP 98928227 A EP98928227 A EP 98928227A EP 0983261 A1 EP0983261 A1 EP 0983261A1
Authority
EP
European Patent Office
Prior art keywords
cyano
substituted
halogen
alkyl
optionally
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP98928227A
Other languages
German (de)
English (en)
Inventor
Otto Schallner
Karl-Heinz Linker
Markus Dollinger
Christoph Erdelen
Ulrike Wachendorff-Neumann
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Bayer AG
Original Assignee
Bayer AG
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Bayer AG filed Critical Bayer AG
Publication of EP0983261A1 publication Critical patent/EP0983261A1/fr
Withdrawn legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • 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 invention relates to new substituted pyridylpyrazoles, processes for their preparation and their use as plant treatment agents, in particular as herbicides, insecticides and acaricides.
  • n the numbers 0 or 1
  • n the numbers 1, 2 or 3
  • Rl for hydrogen, for each optionally by cyano, halogen or C J-C4-
  • Alkoxy substituted alkyl with 1 to 6 carbon atoms, or for each is optionally substituted by cyano or halogen-substituted alkenyl or alkynyl each having 2 to 6 carbon atoms,
  • R 2 for hydrogen, nitro, hydroxy, mercapto, carboxy, cyano, thiocarbamoyl, halogen, for alkyl with 1 to 6 carbon atoms substituted by cyano, halogen or C1-C4alkoxy, or for each optionally with cyano, halogen or C] - C4-alkoxy substituted alkoxy, alkoxycarbonyl, alkylthio, alkylsulfinyl or alkylsulfonyl each having 1 to 6 carbon atoms,
  • R3 represents hydrogen, cyano, halogen or alkyl which has 1 to 6 carbon atoms and is optionally substituted by cyano, halogen or C1-C4alkoxy and
  • R4 for nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, hydroxy, mercapto,
  • R5 for alkyl optionally substituted by cyano, halogen, Cj-C4-alkoxy, Cj-C4-alkylthio, C ⁇ -C4-alkylcarbonyl, C ⁇ -C4-alkoxy-carbonyl or C ⁇ -C4-alkylamino-carbonyl with 1 is up to 6 carbon atoms,
  • R 5 furthermore represents alkenyl or alkynyl, each with 2 to 6 carbon atoms, optionally substituted by cyano, carboxy, halogen, C 1 -C 4 -alkylcarbonyl, C 1 -C 4 -alkoxycarbonyl or C 1 -C 4 -alkylamino-carbonyl.
  • R 5 furthermore for cycloalkyl or cycloalkylalkyl, each optionally substituted by cyano, carboxy, halogen, C1-C4-alkylcarbonyl or C ] -C4-alkoxycarbonyl, each having 3 to 6 carbon atoms in the cycloalkyl group and optionally 1 to 4 carbon atoms in the alkyl part stands,
  • R 5 further for each optionally by hydroxy, mercapto, amino, cyano, carboxy, carbamoyl, thiocarbamoyl, C1 -C4 alkyl, -C-C4-haloalkyl, C ⁇ -C4-alkoxy, C ⁇ -C4-haloalkoxy, C ⁇ -C4-alkylthio C 1 -C 4 haloalkylthio, C 4 -C 4 alkylsulfonyl, C 1 -C 4 alkylsulfonyl, C 4 -C 4 alkylamino or dimethylamino substituted aryl or arylalkyl each having 6 or 10 carbon atoms in the aryl group and optionally 1 to 4 carbon atoms in the alkyl part , or
  • R 5 further for each optionally by hydroxyl, mercapto, amino, cyano, carboxy, carbamoyl, thiocarbamoyl, C] -C4-alkyl, -C -C4-haloalkyl, C ⁇ -
  • Rl has the meaning given above
  • R represents hydrogen or alkyl
  • the new substituted pyridylpyrazoles of the general formula (I) have interesting biological properties which enable them to be used as plant treatment agents. They show strong herbicidal, insecticidal and acaricidal activity and are distinguished in particular by excellent and selective herbicidal activity
  • saturated or unsaturated hydrocarbon radicals such as alkyl, alkenyl or alkynyl, are each straight-chain or branched
  • Halogen generally represents fluorine, chlorine, bromine or iodine, preferably
  • the invention preferably relates to compounds of the formula (I) in which
  • n the numbers 0 or 1
  • n represents the numbers 1, 2 or 3
  • R is hydrogen, for methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, each optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy, or for each optionally by cyano, fluorine , Chlorine or bromine substituted propenyl, butenyl, propynyl or butynyl,
  • R 2 for hydrogen, nitro, hydroxyl, mercapto, carboxy, cyano, thiocarbamoyl, fluorine, chlorine, bromine, for each methyl, ethyl, n- or i-propyl substituted by cyano, fluorine, chlorine, methoxy or ethoxy, n-, i-, s- or t-butyl, or for methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methoxycarbonyl, each optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy , Ethoxycarbonyl, methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, methylsulfinyl, ethylsulfinyl, n
  • R 3 represents hydrogen, fluorine, chlorine, bromine, or methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy, and
  • R 4 for nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, hydroxy, mercapto, amino, hydroxyamino, fluorine, chlorine, bromine or for one of the groupings
  • -QR 5 -NH-R 5 , -NH-OR 5 , -NH-SO 2 -R 5 , -N (SO 2 -R 5 ) 2 .
  • Q is O, S, SO or S0 2
  • Q 1 and Q 2 are each oxygen or sulfur
  • R ⁇ for each optionally by cyano, fluorine, chlorine, methoxy, ethoxy, methylthio, ethylthio, acetyl, propionyl, methoxycarbonyl, ethoxycarbonyl,
  • R 5 furthermore represents cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl or cyclohexylmethyl, each optionally substituted by cyano, carboxy, fluorine, chlorine, bromine, acetyl, propionyl, methoxycarbonyl or ethoxycarbonyl,
  • R 5 further for each optionally by hydroxy, mercapto, amino, cyano, carboxy, carbamoyl, thiocarbamoyl, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, difluoromethyl, trifluoromethyl, methoxy , Ethoxy, n- or i-propoxy, difluoromethoxy, trifluoromethoxy, methylthio, ethylthio, difluoromethylthio, trifluoromethylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl, ethylsulfonyl, methylamino, ethylamino or dimethylamino substituted phenyl, benzyl or benzyl
  • R 5 furthermore each for optionally by hydroxy, mercapto, amino, cyano,
  • the invention particularly relates to the compounds of formula (I) in which
  • n the numbers 0 or 1
  • n stands for the numbers 1, 2 or 3.
  • R 1 each represents methyl or ethyl optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy,
  • R 2 represents hydroxy, mercapto, fluorine, chlorine, bromine, or methyl, ethyl, methoxy, ethoxy, methylthio, ethylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl, each substituted by cyano, fluorine, chlorine, methoxy or ethoxy,
  • R 3 represents fluorine, chlorine, bromine or methyl or ethyl optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy, and
  • R 4 for nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, hydroxy, mercapto, amino, hydroxyamino, halogen or for one of the groupings -QR 5 , -NH-R 5 , -NH-OR 5 , -NH-SO 2 -R 5 , -N (SO 2 -R 5 ) 2 , -CQ ⁇ R 5 , -CQ 1 -Q -R 5 , -CQ NH-R 5 , -Q -CQ!
  • O, S, SO or SO 2 , Q 1 and Q 2 each represent oxygen or sulfur and
  • R 5 for each optionally by cyano, fluorine, chlorine, methoxy, ethoxy, methylthio, ethylthio, acetyl, propionyl, methoxycarbonyl, ethoxycarbonyl,
  • R 5 furthermore represents cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl or cyclohexylmethyl, each optionally substituted by cyano, carboxy, fluorine, chlorine, bromine, acetyl, propionyl, methoxycarbonyl or ethoxycarbonyl,
  • R 5 further for each optionally by hydroxy, mercapto, amino, cyano, carboxy, carbamoyl, thiocarbamoyl, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, difluoromethyl, trifluoromethyl, methoxy , Ethoxy, n- or i-propoxy, difluoromethoxy, trifluoromethoxy, methylthio, ethylthio, difluoromethylthio, trifluoromethylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl, ethylsulfonyl, methylamino, ethylamino or dimethylamino substituted phenyl, benzyl or benzyl
  • R 5 furthermore each for optionally by hydroxy, mercapto, amino, cyano,
  • a particularly preferred group of compounds of the general formula (I) are compounds of the formula (Ia)
  • R 1 , R 2 , R 3 and R 4 have the meanings given above as being particularly preferred.
  • Another particularly preferred group of compounds of the general formula (I) are compounds of the formula (Ib)
  • R 1 , R 2 , R 3 and R 4 have the meanings given above as being particularly preferred.
  • Another particularly preferred group of compounds of the general formula (I) are compounds of the formula (Ic)
  • R 1 , R 2 , R 3 and R 4 have the meanings given above as being particularly preferred.
  • radical definitions listed above apply both to the end products of the formula (I) and correspondingly to the starting or intermediate products required in each case for the preparation. These radical definitions can be combined with one another, that is to say also between the specified preferred ranges.
  • R 1 preferably or in particular has the meaning which has already been mentioned above in connection with the description of the compounds of the formula (I) according to the invention has been indicated preferably or as particularly preferred for R 1
  • the starting materials of the general formula (II) are known synthetic chemicals
  • n, R 2 , R 3 and R 4 preferably or in particular have those meanings which have already been specified above in connection with the description of the compounds of the formula (I) according to the invention preferably or as particularly preferred for n, R 2 , R 3 and R 4
  • n, R 3 and R 4 preferably or in particular have those meanings which have already been mentioned above in connection with the description of the compounds of the formula (I) according to the invention, preferably or as particularly preferred for n, R 3 and R 4 , Q 3 preferably represents oxygen or sulfur and R preferably represents hydrogen or C 1 -C 4 -alkyl, in particular especially for hydrogen, methyl or ethyl
  • Solvent 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
  • Ketones such as acetone, butanone or methyl isobutyl ketone
  • Carboxylic acids e.g. Acetic acid or propionic acid, nitriles such as acetonitrile, propionitrile or butyronitrile
  • Amides such as N, N-dimethylformamide, N, N-dimethylacetamide, N-methyl-formanilide, N-methyl-pyrrolidone or hexamethylphosphoric triamide
  • Esters such as methyl acetate or ethyl acetate, sulfoxides such as dimethyl sulfoxide, alcohols such as methanol, ethanol, n- or i-propanol, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, diethylene glycol monomethyl ether or diethylene glycol monoethyl ether.
  • the usual inorganic or organic bases or acid acceptors are generally suitable as reaction aids for the process according to the invention.
  • These preferably include alkali metal or alkaline earth metal acetates, amides, carbonates, hydrogen carbonates, hydrides, hydroxides or alkanolates, such as, for example, sodium, potassium or calcium acetate, lithium, sodium, potassium or Calcium amide, sodium, potassium or calcium carbonate, sodium, potassium or calcium hydrogen carbonate, lithium, sodium, potassium or calcium hydride.
  • reaction temperatures can be varied within a substantial range when carrying out the process according to the invention. In general, temperatures between 0 ° C and 150 ° C, preferably between 20 ° C and 120 ° C.
  • the process according to the invention is generally carried out under normal pressure. However, it is also possible to carry out the process according to the invention under elevated or reduced pressure - generally between 0.1 bar and 10 bar.
  • the starting materials are generally used in approximately equimolar amounts. However, it is also possible to use one of the components in a larger excess.
  • the reaction is generally carried out in a suitable diluent and the reaction mixture is generally stirred for several hours at the required temperature. Working up is carried out according to customary methods (cf. the production examples).
  • 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 all plants that grow 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: Dicotyledonous weeds of the genera - Sinapis, Lepidium, Galium, Stellaria, Matricaria, Anthemis, Galinsoga, Chenopodium, Urtica, Senecio, Amaranthus, Portulaca, Xanthium, Convolvulus, Ipomoea, Polygonum, Sesbania, Ambrosia, Cirsium, Carduippum, Sonuanum , Rotala, Lindernia, Lamium, Veronica, Abutilon, Emex, Datura, Viola, Galeopsis, Papaver, Centaurea, Trifolium,
  • the compounds are suitable for total weed control, for example on industrial and rail tracks and on paths and squares with and without tree cover.
  • the compounds for weed control in permanent crops for example forest, ornamental wood, fruit, wine, Citrus, nut, banana, coffee, tea, gum, oil palm, cocoa, berry fruit and hop systems, on ornamental and sports turf and pasture fields and for selective weed control in annual crops
  • the compounds of formula (I) according to the invention are particularly suitable for the selective control of monocotyledon and dicotyledon weeds in monocotyledon and dicotyledon crops both in the pre-emergence and in the post-emergence process.
  • the active compounds are suitable for controlling animal pests, preferably
  • Arthropods and nematodes especially insects and arachnids, which are found in agriculture, in forests, in the protection of stored goods and materials, and in the hygiene sector. They are effective against normally sensitive and resistant species as well as against all or individual stages of development.
  • the pests mentioned above include:
  • Isopoda e.g. Oniscus asellus, Armadillidium vulgare, Porcellio scaber.
  • Thysanura e.g. Lepisma saccharina.
  • Thysanoptera e.g. Hercinothrips femoralis, Thrips tabaci.
  • Homoptera e.g
  • Lepidoptera e.g. Pectinophora gossypiella, Bupalus piniarius, Cheimatobia brumata, Lithocolletis blancardella, Hyponomeuta padella, Plutella maculipennis, Malacosoma neustria, Euproctis chrysorrhoea, Lymantria spp.
  • Tineola bisselliella Tinea pellionella, Hofmannophila pseudospretella, Cacoecia podana, Capua reticulana, Choristoneura glamiferana, Clysia ambiguella, Homona magnanima, Tortrix viridana.
  • spp. spp., spp., Meligethes aeneus, Ptinus spp., Niptus hololeucus, Gibbium psylloides, Tribolium spp., Tenebrio molitor, Agriotes spp.,
  • Conoderus spp. Melolontha melolontha, Amphimallon solstitialis, Costelytra zealandica.
  • Hymenoptera e.g. Diprion spp., Hoplocampa spp., Lasius spp., Monomorium pharaonis, Vespa spp.
  • Acarina e.g. Acarus siro, Argas spp., Ornithodoros spp., Dermanyssus gallinae, Eriophyes ribis, Phyllocoptruta oleivora, Boophilus spp., Rhipicephalus spp., Amblyomma spp., Hyalomma spp., Ixodes spp., Psoroptes spp.,
  • Chorioptes spp. Sarcoptes spp., Tarsonemus spp., Bryobia praetiosa, Panonychus spp., Tetranychus spp ..
  • Plant-parasitic nematodes include e.g. Pratylenchus spp., Radopholus spp., Ditylenchus spp., Tylenchulus spp., Heterodera spp., Globodera spp.,
  • Meloidogyne spp. Aphelenchoides spp., Longidorus spp., Xiphinema spp., Trichodorus spp, Tylenchus spp., Helicotylenchus spp, Rotylenchus spp, Tylenchulus spp.
  • the active compounds can be converted into the customary formulations, such as solutions, emulsions, wettable powders, suspensions, powders, dusts, pastes, soluble powders, granules, suspension emulsion concentrates, active substance-impregnated natural and synthetic substances and very fine encapsulations in polymeric substances.
  • formulations are prepared in a known manner, e.g. B. by mixing the active ingredients with extenders, that is liquid solvents and / or solid carriers, optionally using surface-active agents, ie emulsifiers and / or dispersants and / or foam-generating agents
  • Liquid solvents are essentially: aromatics, such as xylene, toluene, or alkyl naphthalenes, chlorinated aromatics and chlorinated aliphatic hydrocarbons, such as chlorobenzenes, Chlorethylene or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, for example Petroleum fractions, mineral and vegetable oils, alcohols such as butanol or glycol and their ethers and esters, ketones such as
  • Solid carrier materials that come into question are, for example, ammonium salts and natural rock powders such as kaolins, alumina, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic rock powders such as highly disperse silica, aluminum oxide and silicates.
  • Solid carrier materials for granules are suitable '' e.g. broken and fractionated natural rocks such as calcite, marble, pumice, sepiolite, dolomite as well as synthetic granules from inorganic and organic flours as well as granules from organic material such as sawdust,
  • coconut shells, corn cobs and tobacco stalks are suitable as emulsifying and / or foaming agents, for example nonionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkyl aryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates and protein hydrolysates, and dispersants include, for example, lignin sulfite liquor and methyl cellulose.
  • nonionic and anionic emulsifiers such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkyl aryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates and protein hydrolysates
  • dispersants include, for example, lignin sulfite liquor and methyl cellulose.
  • Adhesives such as carboxymethyl cellulose, natural and synthetic powdery, granular or latex-shaped polymers, 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, for example 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 zinc 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 in a mixture with known herbicides for combating weeds, finished formulations or tank mixes being possible
  • Acetochlor Acifluorfen (-sodium), Aclonifen, Alachlor, Alloxydim (-sodium), Ametryne, Amidochlor, Amidosulf ron, Asulam, Atrazine, Azimsul wholeon, Benazolin, Ben rolesesate, Bensul matterson (-methyl), Bentazon, Benzofenap-Benzethyllprop , Bialaphos, Bifenox, Bromobutide, Bromofenoxim, Bromoxynil, Butachlor, Butylate, cafenstrole, Carbetamides, Chlomethoxyfen, Chloramben, Chloridazon, Chlorimuron (- ethyl), Chlornitrofen, Chlorsul dominanton, Chlortoluron, Cinmethylin, Clethodimphonyl, Clonimphonyl, Clonimorphonin, Cinosulfuron, Cinosulfuron, Cinos
  • Tribenuron (-methyl), triclopyr, tridiphane, trifluralin and triflusulmati.
  • 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 compounds can be used as such, in the form of their formulations or in the use forms prepared therefrom by further dilution, such as ready-to-use solutions, suspensions, emulsions, powders, pastes and granules. They are used in the customary manner, for example by watering, spraying, spraying or scattering.
  • the active compounds according to the invention can be applied both before and after the plants emerge. 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 1 g and 10 kg of active ingredient per hectare of soil, preferably between 5 g and 5 kg per ha.
  • Example 1 1 Dichloromethane, 2-chloro-5- (4-bromo-5-difluoro-methoxy-1-methyl-1H-pyrazol-3-yl) pyridine (“Example 1 1”) of melting point 60 ° is obtained in a similar yield C.
  • a solution of 23.3 g (0.15 mol) is added dropwise to a suspension of 33.6 g (0.3 mol) of potassium t-butoxide in 210 ml of tetrahydrofuran at -40 ° C. in the course of 15 minutes.
  • Acetyl-2-chloropyridine in 50 ml tetrahydrofuran.
  • the mixture is stirred at -40 ° C. for 30 minutes and then mixed with 11.4 g (0.15 mol) of carbon disulphide. After a further 30 minutes, 42.6 g (0.3 mol) of methyl iodide are added and the reaction mixture is allowed to come to room temperature within two hours.
  • the reaction mixture is poured onto 1.5 l of ice water, adjusted to pH 2 to 3 with 1N hydrochloric acid and extracted with 1.5 liters of ethyl acetate.
  • the organic phase is washed with sodium chloride solution, dried over magnesium sulfate and freed from the solvent in vacuo.
  • the crude product obtained is stirred with about 100 ml of diethyl ether, the precipitated solid is filtered off and dried.
  • Seeds of the test plants are sown in normal soil. After about 24 hours, the soil is watered with the active ingredient preparation.
  • the amount of water per unit area is expediently kept constant.
  • the concentration of active ingredient in the preparation is irrelevant; the decisive factor is only the amount of active ingredient applied per unit area
  • Emulsifier 1 part by weight of alkylaryl polyglycol ether
  • Test plants which have a height of 5-15 cm are sprayed with the active substance preparation, so that the desired amounts of active substance are applied per unit area.
  • the concentration of the spray liquor is chosen so that in
  • the degree of damage to the plants is rated in% damage compared to the development of the untreated control.
  • the effect is determined in%. 100% means that all spider mites have been killed, 0% means that none of the spider mites have been killed
  • the compound according to Preparation Example 1 shows a degree of death of 95% after 7 days at an active ingredient concentration of 0.01%
  • a specified amount of active ingredient preparation of the desired concentration is pipetted onto a standardized amount of artificial feeder. After the methanol has evaporated, one larva (L 2 -L 3 ) of the army worm (Spodoptera frugiperda) is placed on the feed in triplicate
  • the effect is determined in%. 100% means that all animals have been killed, 0% means that no animals have been killed
  • connection according to Production Example 2 is shown in a

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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)
  • Plural Heterocyclic Compounds (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

L'invention concerne de nouveaux pyridylpyrazoles de la formule générale (I), dans laquelle: m représente le nombre 0 ou 1; n représente le nombre 1, 2 ou 3; R<1> représente hydrogène, alkyle C1-C6 éventuellement substitué par cyano, par halogène, ou par alcoxy C1-C4, ou bien alcényle C2-C6 ou alkinyle C2-C6 éventuellement substitués par cyano ou bien halogène; R<1> représente hydrogène, nitro, hydroxy, mercapto, carboxy, cyano, thiocarbamoyle, halogène, alkyle substitué par cyano, halogène ou alcoxy C1-C4, ou bien alcoxy, alcoxycarbonyle, alkylthio, alkylsulfinyle ou alkylsulfonyle, qui possèdent chacun 1 à 6 atomes de carbone et peuvent éventuellement être substitués par cyano, halogène ou alcoxy C1-C4; R<3> représente hydrogène, cyano, halogène ou bien alkyle C1-C6 éventuellement substitué par cyano, halogène ou alcoxy C1-C4; et R<4> représente nitro, cyano, carboxy, carbamoyle, thiocarbamoyle, hydroxy, mercapto, amino, hydroxyamino, halogène ou un des groupements -Q-R<5>, -NH-R<5>, -NH-O-R<5>, -NH-SO2-R<5>, -N(SO2-R<5>)2, -CQ<1>-R<5>, -CQ<1>-Q<2>-R<5>, -CQ<1>-NH-R<5>, -Q<2>-CQ<1>-R<5>, -NH-CQ<1>-R<5>, -N(SO2-R<5>)(CQ<1>-R<5>), -Q<2>-CQ<1>-Q<2>-R<5>, -NH-CQ<1>-Q<2>-R<5> ou bien -Q<2>-CQ<1>-NH-R<5>, où Q représente O, S, SO ou SO2, Q<1> and Q<2> représentent chacun oxygène ou soufre, R<5> à la signification donnée dans la description. L'invention concerne également un procédé de préparation de ces pyridylpyrazoles et leur utilisation comme agents phytosanitaires, en particulier comme herbicides, insecticides et acaricides.
EP98928227A 1997-05-20 1998-05-07 Pyridylpyrazoles substitues comme herbicides, insecticides et acaricides Withdrawn EP0983261A1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE1997121031 DE19721031A1 (de) 1997-05-20 1997-05-20 Substituierte Pyridylpyrazole
DE19721031 1997-05-20
PCT/EP1998/002676 WO1998052938A1 (fr) 1997-05-20 1998-05-07 Pyridylpyrazoles substitues comme herbicides, insecticides et acaricides

Publications (1)

Publication Number Publication Date
EP0983261A1 true EP0983261A1 (fr) 2000-03-08

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EP98928227A Withdrawn EP0983261A1 (fr) 1997-05-20 1998-05-07 Pyridylpyrazoles substitues comme herbicides, insecticides et acaricides

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EP (1) EP0983261A1 (fr)
JP (1) JP2001526669A (fr)
CN (1) CN1257490A (fr)
AU (1) AU8015598A (fr)
BR (1) BR9815524A (fr)
CA (1) CA2290379A1 (fr)
DE (1) DE19721031A1 (fr)
WO (1) WO1998052938A1 (fr)

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AU2003274025A1 (en) * 2002-10-17 2004-05-04 Syngenta Participations Ag Pyridine derivatives useful as herbicides
WO2004035563A1 (fr) * 2002-10-17 2004-04-29 Syngenta Participations Ag Derives de 3-heterocyclylpyridine utilises comme herbicides
CN100427481C (zh) 2005-05-26 2008-10-22 沈阳化工研究院 一种芳基醚类化合物及其制备与应用
ES2524045T3 (es) * 2008-06-13 2014-12-03 Bayer Cropscience Ag Nuevas amidas y tioamidas heteroaromáticas como plaguicidas
EP2591674B1 (fr) 2008-07-17 2016-01-13 Bayer CropScience AG Liaisons hétérocycliques en tant que moyen de lutte contre les parasites
AU2012215741A1 (en) * 2011-02-09 2013-08-22 Nissan Chemical Industries, Ltd. Pyrazole derivative and pest control agent
PE20161143A1 (es) 2014-01-16 2016-11-18 Du Pont Derivados de pirimidiniloxi benceno como herbicidas
RU2735278C2 (ru) 2015-03-18 2020-10-29 ЭфЭмСи Корпорейшн Замещенные производные пиримидинилокси-пиридина в качестве гербицидов
TWI713530B (zh) 2015-06-05 2020-12-21 美商艾佛艾姆希公司 作為除草劑之嘧啶氧基苯衍生物
BR112018000687B1 (pt) 2015-07-13 2021-05-04 Fmc Corporation composto, composições herbicidas, misturas herbicidas e métodos para o controle do crescimento de vegetação indesejada
TW201904947A (zh) 2017-05-02 2019-02-01 美商富曼西公司 作為除草劑的嘧啶氧基苯稠合化合物

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Also Published As

Publication number Publication date
BR9815524A (pt) 2000-11-21
CA2290379A1 (fr) 1998-11-26
WO1998052938A1 (fr) 1998-11-26
DE19721031A1 (de) 1998-11-26
AU8015598A (en) 1998-12-11
CN1257490A (zh) 2000-06-21
JP2001526669A (ja) 2001-12-18

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