EP1084111A1 - Substituted 3-thiocarbamoylpyrazoles - Google Patents

Substituted 3-thiocarbamoylpyrazoles

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Publication number
EP1084111A1
EP1084111A1 EP99925024A EP99925024A EP1084111A1 EP 1084111 A1 EP1084111 A1 EP 1084111A1 EP 99925024 A EP99925024 A EP 99925024A EP 99925024 A EP99925024 A EP 99925024A EP 1084111 A1 EP1084111 A1 EP 1084111A1
Authority
EP
European Patent Office
Prior art keywords
alkyl
alkoxy
phenyl
halogen atoms
substituents
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Withdrawn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
EP99925024A
Other languages
German (de)
French (fr)
Inventor
Bernd Alig
Albrecht Marhold
Jörn Stölting
Wolfgang Gau
Christoph Erdelen
Andreas Turberg
Norbert Mencke
Olaf Hansen
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 CropScience AG
Original Assignee
Bayer AG
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Filing date
Publication date
Application filed by Bayer AG filed Critical Bayer AG
Publication of EP1084111A1 publication Critical patent/EP1084111A1/en
Withdrawn legal-status Critical Current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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/26—Radicals substituted by halogen atoms or nitro radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
    • C07D213/61—Halogen atoms or nitro radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D231/16—Halogen atoms or nitro radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D231/38—Nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D231/44—Oxygen and nitrogen or sulfur and nitrogen atoms

Definitions

  • the invention relates to new substituted 3-thiocarbamoylpyrazoles, several processes for their preparation and their use as pesticides.
  • R 1 stands for H 2 N-CS-
  • n the numbers 0 or 1
  • R 2 represents the numbers 0, 1 or 2, R 2 for alkyl, alkenyl, alkynyl, cyanoalkyl, thiocyanatoalkyl, nitroalkyl, alkyl - thioalkyl, alkylsulfinylalkyl, alkylsulfonylalkyl, haloalkylthioalkyl, haloalkylsulfinylalkyl, haloalkylsulfonylalkyl, alkenylthioalkyl, alkenylsulfinylalkyl, alkenylsulfonylalkyl.
  • Arylalkylsulfinylalkyl or arylalkylsulfonylalkyl is arylalkylsulfinylalkyl or arylalkylsulfonylalkyl
  • Trialkylsilylethinyl optionally substituted aryloxy or for one of the following groups:
  • R 4 and R 5 independently of one another represent hydrogen, cyano, alkyl or in each case optionally substituted aryl or aralkyl, R 6 represents hydrogen or alkyl,
  • R 7 represents hydrogen, alkyl or optionally substituted aralkyl
  • R 8 represents alkyl or haloalkyl
  • R 9 represents alkyl
  • R 10 represents alkyl, haloalkyl, alkoxyalkyl or in each case optionally substituted phenyl, phenoxy or pyridyl,
  • R 1 1 represents alkyl, alkenyl, alkynyl, formyl, alkylcarbonyl, haloalkylcarbonyl or alkoxycarbonyl,
  • R 17 and R 18 are independently alkyl and
  • Y represents oxygen or sulfur
  • R 13 represents hydrogen, alkyl, alkoxyalkyl, propargyl, allyl, alkoxycarbonyl, alkylcarbonyl, optionally substituted benzyl or the grouping -CO-C (R 14 , R 15 , R 16 ),
  • R 14 represents hydrogen, alkyl, haloalkyl, halogen or optionally substituted phenyl and
  • R 14 and R 15 together with the carbon atom to which they are attached, for a 3- to 7-membered ring system with optionally up to two
  • X represents oxygen or sulfur
  • Ar stands for optionally substituted phenyl or pyridyl.
  • R 3 " 1 represents one of the following groupings: -NHR11, -OR12 or -NR13-CX-C (R14, R15, R16),
  • R 2 has the meaning given above and
  • oxidized with oxidizing agents optionally in the presence of a diluent and optionally in the presence of a catalyst.
  • Control of animal pests in particular insects, arachnids and nematodes, which are found in agriculture, in forests, in the protection of stored goods and materials and in the hygiene sector.
  • the compounds according to the invention are generally defined by the formula (I).
  • R 2 preferably represents (C r C 6 ) alkyl, (C 2 -C 6 ) alkenyl, (C 2 -C 6 ) alkynyl, cyano-
  • Halogen atoms (C 2 -C 6 ) alkenylthio- (C. -C 4 ) alkyl 1, (C 2 -C 6 ) - alkenylsul- f ⁇ nyl- (C, -C 4 ) alkyl, (C 2 -C 6 ) -Alkenylsulfonyl- (C i -C 4 ) alkyl, (C 2 -C 6 ) - alkynylthio- (C ⁇ -C 4 ) alkyl, (C 2 -C 6 ) alkynylsulfionyl- (C, -C 4 ) alkyl, (C 2 -C 6 ) - alkynylsulfonyl- (C, -C 4 ) alky 1, (C, -C 4 ) - alkoxy-carbony 1- (C, -C 4 ) -alkyl, (C, - C 4 )
  • Halogen (C r C 6 ) alkyl, (C 2 -C 6 ) alkenyl, (C r C 6 ) alkoxy. (C 2 -C 6 ) alkynyloxy, (C, -C 4 ) alkylthio, (C, -C 4 ) alkylsulfmy 1, (C r C 4 ) alkylsulfonyl; (C r C 6 ) haloalkyl, (C 2 -C 4 ) haloalkenyl, (C ] -C 4 ) haloalkoxy, (C r C 4 ) haloalkylthio, (C r C 4 ) haloalkylsulfmyl and (C, -C 4 ) -Halogenated alkyl sulfonyl, each with 1 to 5 halogen atoms; Cyano, nitro, hydroxy, hydrazino, (C r C 6 )
  • Halogen atoms (C] -C 4 ) alkoxy or (C j -C) haloalkoxy and (C ] -C 4 ) - Haloalkylthio with 1 to 5 halogen atoms each substituted phenyf or phenoxy, SF 5
  • R 'and R "independently of one another represent hydrogen or (C r C 6 ) -alkyl and
  • Z represents -CO or -SO 2 .
  • m 0 additionally preferably for thiocyanato, chlorine, bromine, iodine, nitro, cyano, hydroxy, chlorosulfonyl, (C r C 4 ) alkoxy, (C 2 -C 4 ) alkenyloxy; (C r C 4 ) haloalkyl, (C 2 -C 4 ) haloalkenyl, (C r
  • R 4 and R 5 are, independently of one another, preferably for hydrogen, cyano, (C, -C 4 ) alkyl or for in each case optionally up to five times, the same or different substituted phenyl or benzyl, where the phenyl substituents already mentioned above for R 2 are suitable as substituents.
  • R 6 preferably represents hydrogen or (C i -C) alkyl.
  • R 7 preferably represents hydrogen (C r C 4 ) alkyl or optionally mono- to pentasubstituted, identically or differently substituted benzyl, the phenyl substituents already mentioned above for R 2 being suitable as substituents.
  • R 8 preferably represents (C r C 4 ) alkyl or (C r C 4 ) haloalkyl having 1 to 5 halogen atoms.
  • R 9 preferably represents (CC 4 ) alkyl.
  • preferably hydrogen, amino, chlorine, bromine, iodine or one of the following groups:
  • RIO is preferred for (C 1 -C 4 ) alkyl, (C r C 4 ) haloalkyl with 1 to 5 halogen atoms, (C] -C 4 ) alkoxy- (C ] -C 4 ) alkyl or for each is optionally monosubstituted to pentasubstituted, identically or differently, phenyl, phenoxy or pyridyl, the phenyl substituents already mentioned above for R 2 being suitable as substituents, R 1 1 preferably for (C r C 4 ) alkyl, (C 2 -C 4 ) alkenyl, (C 2 -C 4 ) alkynyl, - formyl, (C r C 4 ) alkyl carbonyl, (C ⁇ -C 4 ) haloalkyl carbonyl having 1 to 5 halogen atoms or (-C-C 4 ) alkoxy carbonyl,
  • R 12 preferably for (C, -C 4 ) alkyl, (C 2 -C 4 ) alkenyl, (C 2 -C 4 ) alkynyl, di- (-C-C) alkylamino- (C r C 4 ) -alkyl; optionally mono- to pentasubstituted, identically or differently substituted, phenyl (C ) -C 2 -alkyl, where the phenyl substituents already mentioned above for R 2 are suitable as substituents;
  • R 17 and R 18 independently of one another preferably represent (C r C 4 ) -alkyl and
  • Y represents oxygen or sulfur
  • R 13 preferably represents hydrogen, (C r C 4 ) -alkyl, (C, -C 4 ) -alkoxy- (C, -C 4 ) -alkyl, propargyl, allyl, (C r C 4 ) -alkoxy-carbonyl, (C 1 -C 4 ) -alkylcarbonyl, stands for benzyl which is optionally monosubstituted to pentasubstituted by identical or different substituents, the phenyl substituents already mentioned above for R 2 being suitable as substituents,
  • R ' 4 preferably represents hydrogen, (C, -C 4 ) alkyl, halogen, (C, -C 4 ) haloalkyl having 1 to 5 halogen atoms or optionally optionally up to five times, identical or differently substituted phenyl, where as Substituents which are suitable for phenyl substituents already mentioned above for R 2 ,
  • R 15 is preferably hydrogen, (Cj-C) -alkyl, halogen, (-C-C 4 ) -haloalkyl and (C ⁇ -C) -haloalkoxy- (C ] -C) alkyl, each with 1 to 5
  • R 14 and R 15 together with the carbon atom to which they are attached preferably represent a 5- to 6- or 7-membered ring system which may optionally have up to two identical or different hetero atoms, such as O, S or Can contain N atoms,
  • X preferably represents oxygen or sulfur.
  • Ar preferably represents phenyl or pyridyl which is in each case monosubstituted to trisubstituted by identical or different substituents, the phenyl substituents already mentioned above for R 2 being suitable as substituents.
  • R 2 particularly preferably represents (CC 4 ) - alkyl, (C 2 -C 4 ) - alkenyl, (C 2 -C 4 ) -
  • Cyan- (C, -C 2 ) alkyl Thiocyanato- (C r C 2 ) -alkyl, nitro- (C, -C 2 ) -alkyl, (C, -C 4 ) -alkylthio- (C r C 2 ) -alkyl, (C, -C 4 ) - Alkylsulfionyl (C r C 2 ) alkyl,
  • R 'and R "independently of one another represent hydrogen or (C r C 4 ) alkyl and
  • Z represents -CO or -S0 2 .
  • R 3 particularly preferably represents hydrogen, amino, chlorine, (C r C 4 ) -alkylamino and the group -NH-CO-R 10
  • R 10 is particularly preferably for (C r C 4 ) alkyl, (C r C) haloalkyl having 1 to 5 identical or different halogen atoms from the series fluorine, chlorine and bromine and for phenyl which is monosubstituted to disubstituted by identical or different substituents and phenoxy stands, with the phenyl substituents already mentioned above for R 2 being suitable as substituents.
  • Ar particularly preferably represents in each case optionally one to three times, identical or different by fluorine, chlorine, bromine; (C r C 2 ) haloalkyl and
  • R 'and R independently of one another represent hydrogen or (C i -C) alkyl
  • Z represents CO or SO 2
  • Hydrazino dimethylhydrazino, amino, methylamino, dimethylamino, cyano, methylthio, -CONH 2 , -CSNH 2 , phenyl, chlorophenyl, fluorophenyl, dichlorophenyl, phenoxy, chlorophenoxy, fluorophenoxy and dichlorophenoxy.
  • R 3 very particularly preferably represents hydrogen. Amino, chlorine, -NHCH-
  • Ar very particularly preferably represents phenyl which is substituted twice or three times, identically or differently by F, Cl, Br, CF 3 , OCF 3 , SCF 3 , SOCF 3 , SO 2 CF 3 , OCH 2 CF 3 , CH 3 or SF 5 or 2-pyridyl.
  • hydrocarbon radicals such as alkyl or alkenyl - also in compounds with heteroatoms such as alkoxy or allythio - are in each case straight-chain or branched as far as possible.
  • Ar, R 2 , R 3 , m and n stand for the abovementioned general, preferred, particularly preferred and very particularly preferred meanings.
  • Table 2 contains compounds of the general formula (IB), in which
  • Table 3 contains compounds of the general formula (IB), in which
  • Table 4 contains compounds of the general formula (IB), in which
  • Table 5 contains compounds of the general formula (IB), in which and for R 2 , n and R 3 the substituent combinations as listed in Table 1 apply.
  • Table 6 contains compounds of the general formula (IB), in which
  • Table 7 contains compounds of the general formula (IB), in which
  • Table 8 contains compounds of the general formula (IB), in which
  • Table 9 contains compounds of the general formula (IB), in which
  • Table 10 contains compounds of the general formula (IB) in which H,
  • Table 11 contains compounds of the general formula (IB), in which
  • Table 12 contains compounds of the general formula (IB), in which and for R 2 , n and R 3 the substituent combinations as listed in Table 1 apply.
  • reaction sequence of process (b) according to the invention can be represented by the following formula:
  • the 3-cyanopyrazole derivatives of the formula (II) to be used as starting materials for carrying out process (a) according to the invention are known (cf. for example EP 0 295 117, GB 2 308 365, WO 98/04 530 and WO 97/07 102 ) and / or can be produced in analogy to known processes.
  • the compounds of formula (III) can be obtained by using 2-cyanopyrazoles of formula (V)
  • Ar and R 3 ⁇ ! have the meaning given above, according to process (a) according to the invention with hydrogen sulfide, if appropriate - in the presence of a reaction auxiliary and if appropriate in the presence of a diluent.
  • the 3-cyanopyrazoles of the formula (V) are known (cf. e.g. EP 659 745) or they can be obtained by generally customary processes.
  • the sulfenyl halides of the formula (IV) which are also to be used as starting materials for process (b) according to the invention are generally known compounds of organic chemistry and / or can be prepared by known processes.
  • the 3-thiocarbamoylpyrazole derivatives of the formula (Ia) to be used as starting materials for process (c) according to the invention are compounds according to the invention.
  • Process (a) according to the invention is preferably carried out using a diluent.
  • a diluent Practically all inert organic solvents can be used as diluents. These preferably include aliphatic and aromatic, optionally halogenated hydrocarbons such as pentane,
  • All bases which can usually be used for such reactions can be used as reaction auxiliaries in process (a) according to the invention.
  • front- Basic nitrogen compounds such as trimethylamine 5 triethylamine, tripropylamine, tributylamine, diisobutylamine, dicyclohexylamine, ethyldiisopropylamine, ethyldicyclohexylamine, N, N-dimethylbenzylamine, N, N-dimethyl-aniline, pyridine, 2-methyl-, 3-methyl, are also suitable.
  • DBN 1,5-diazabicyclo- [5,4,0] -undec-7-ene
  • DBU 1,4-diazabicyclo- [2,2,2] octane
  • DABCO 1,4-diazabicyclo- [2,2,2] octane
  • reaction temperatures can be varied within a substantial range in process (a) according to the invention. In general, temperatures between 0 ° C and 100 ° C, preferably at temperatures between 10 ° C and 80 ° C.
  • Process (a) according to the invention is generally carried out under normal pressure. However, it is also possible to work under increased or reduced pressure.
  • the hydrogen sulfide is generally used in excess.
  • the reactions are generally carried out in a suitable diluent in the presence of a basic nitrogen compound. Working up is carried out using customary methods (cf. the production examples).
  • Inert organic solvents are suitable as diluents for carrying out process (b) according to the invention.
  • These include in particular aliphatic, alicyclic or aromatic, optionally halogenated hydrocarbons, such as, for example, gasoline, benzene, toluene, xylene, chlorobenzene, petroleum ether, hexane, cyclohexane, dichloromethane, chloroform, carbon tetrachloride; Ethers such as diethyl ether, dioxane, tetrahydrofuran or ethylene glycol dimethyl or diethyl ether, ketones such as acetone or butanone, nitriles such as acetonitrile or propionitrile: Amides such as dimethylformamide, dimethylacetamide, N-methylformanilide, N-methylpyrrolidone or hexamethylphosphoric acid triamide, esters such as ethyl acetate, sulfox
  • process (b) according to the invention can be carried out in the presence of a reaction auxiliary.
  • All conventional inorganic or organic bases are suitable as such. These include, for example, alkali metal hydroxides, such as sodium hydroxide or potassium hydroxide, alkali metal carbonates or hydrogen carbonates, such as sodium carbonate, potassium carbonate or sodium hydrogen carbonate, and tertiary amines, such as triethylamine, N, N-dimethylaniline, pyridine, N, N-
  • DBU diazabicyclooctane
  • DABCO diazabicyclooctane
  • DBN diazabicyclonones
  • DBU diazabicycloundecene
  • reaction temperatures can be varied within a substantial range when carrying out process (b) according to the invention. In general, temperatures between -20 ° C and + 120 ° C, preferably at temperatures between 0 ° C and + 50 ° C.
  • reaction auxiliaries preferably 1.0 to 1.5 mol of sulfenyl halide of the formula (IV) and optionally 1.0 to 2.5 mol, preferably 1.0 to 1.5 mol of reaction auxiliaries.
  • the reaction, working up and isolation of the reaction products is carried out according to generally customary methods.
  • Suitable oxidizing agents for carrying out process (c) according to the invention are all customary oxidizing agents which can be used for sulfur oxidation. Hydrogen peroxide, organic peracids such as peracetic acid, m-chloroperbenzoic acid, p-nitroperbenzoic acid or atmospheric oxygen are particularly suitable. Inert organic solvents are also suitable as diluents for carrying out process (c) according to the invention.
  • Hydrocarbons such as gasoline, benzene, toluene, hexane or petroleum ether, are preferably used; chlorinated hydrocarbons, such as dichloromethane, 1, 2-dichloroethane, chloroform, carbon tetrachloride or chlorobenzene; Ethers, such as diethyl ether, dioxane or tetrahydrofuran; Carboxylic acids, such as acetic acid or propionic acid, or dipolar aprotic solvents, such as acetonitrile, acetone, ethyl acetate or dimethylformamide.
  • chlorinated hydrocarbons such as dichloromethane, 1, 2-dichloroethane, chloroform, carbon tetrachloride or chlorobenzene
  • Ethers such as diethyl ether, dioxane or tetrahydrofuran
  • Carboxylic acids such as acetic acid or propionic acid, or dipolar
  • process (c) according to the invention can be carried out in the presence of an acid binder.
  • an acid binder As such, all commonly used organic and inorganic acid binders come into question.
  • process (c) according to the invention can be carried out in the presence of a suitable catalyst.
  • a suitable catalyst All metal salt catalysts customarily used for such sulfur oxidations are suitable as such. Examples include ammonium molybdate and sodium tungstate.
  • reaction temperatures can be varied within a substantial range when carrying out process (c) according to the invention. Generally one works at temperatures between -20 ° C and + 70 ° C. preferably at temperatures between 0 ° C and + 50 ° C.
  • 0.8 to 1.2 moles, preferably equimolar amounts, of oxidizing agent are generally used per mole of compound of the formula (Ia) if one wishes to interrupt the oxidation of the sulfur at the sulfoxide stage.
  • 1.8 to 3.0 mol, preferably twice, are generally employed per mole of compound of the formula (Ia) molar amounts of oxidizing agent.
  • the reaction, workup and isolation of the end products is carried out by customary methods.
  • the active substances are suitable for controlling animal pests, in particular insects, arachnids and nematodes, which occur in agriculture, in forests, in the protection of stored goods and materials, and in the hygiene sector. They can preferably be used as pesticides. 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.
  • Orthoptera e.g. Blatta orientalis, Periplaneta americana, Leucophaea maderae, Blattella germanica, Acheta domesticus, Gryllotalpa spp., Locusta migratoria migratorioides, Melanoplus differentialis, Schistocerca gregaria.
  • Thysanoptera e.g. Hercinothrips femoralis, Thrips tabaci.
  • Hymenoptera e.g. Diprion spp., Hoplocampa spp., Lasius spp., Monomorium pharaonis, Vespa spp.
  • Dacus oleae Tipula paludosa.
  • 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 ., Tarsonemus spp., Bryobia praetiosa, Panonychus spp., Tetranychus spp ..
  • Plant-parasitic nematodes include e.g. Pratylenchus spp., Radopholus similis, Ditylenchus dipsaci, Tylenchulus semipenetrans, Heterodera spp., Globodera spp., Meloidogyne spp., Aphelenchoides spp., Longidorus spp., Xiphinema spp.,
  • the compounds of the formula (I) according to the invention are notable in particular for their high insecticidal activity. They can be used with particularly good success in combating plant-damaging insects, such as, for example, against the caterpillars of the owl butterfly (Spodoptera frugiperda) or the peach aphid
  • 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, impregnated with active compounds
  • formulations are made in a known manner, e.g. by mixing the active ingredients with extenders, that is to say liquid solvents and / or solid carriers, if appropriate using surface-active agents, that is to say
  • Emulsifiers and / or dispersants and / or foaming agents Emulsifiers and / or dispersants and / or foaming agents.
  • organic solvents can also be used as auxiliary solvents.
  • auxiliary solvents e.g. organic solvents
  • aromatics such as xylene, toluene, or alkylnaphthalenes
  • chlorinated aromatics and chlorinated aliphatic hydrocarbons such as chlorobenzenes, chlorethylenes or methylene chloride
  • aliphatic hydrocarbons such as cyclohexane or paraffins, e.g.
  • Petroleum fractions mineral and vegetable oils, alcohols such as butanol or glycol and their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar
  • Solvents such as dimethylformamide and dimethyl sulfoxide, and water.
  • ammonium salts and natural rock powder such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonil or diatomaceous earth and synthetic table stone powders such as highly disperse silica, aluminum oxide and silicates, - are suitable as solid carriers for granules: e.g.
  • suitable emulsifying and or foam-generating agents are: for example nonionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates and protein hydrolyzates;
  • Possible dispersing agents are, for example, lignin sulfite waste 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, 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 zinc can be used.
  • the formulations generally contain between 0.1 and 95% by weight of active compound, preferably between 0.5 and 90%.
  • the active substance according to the invention can be present in its commercially available formulations and in the use forms prepared from these formulations in a mixture with other active substances, such as insecticides, attractants, sterilants, bactericides, acaricides, nematicides, fungicides, growth-regulating substances or herbicides.
  • Insecticides include, for example, phosphoric acid esters, Carbamates, carboxylic acid esters, chlorinated hydrocarbons, phenylureas, - substances produced by microorganisms etc.
  • Famoxadon Fenapanil, Fenarimol, Fenbuconazol, Fenfuram, Fenitropan, Fenpiclonil, Fenpropidin, Fenpropimo ⁇ h, Fentinacetat, Fentinhydroxyd, Ferbam, Ferimzon, Fluazinam, Flumetover, Fluoromid, Fluquinconazol, Flu ⁇ rimidol, Flusrimidol, Flusrimidol, Flusrilidol, Flusrilidol, Flusrilidol, Flusrilidol, Flusrilidol, Flusrilidol, Flusrilidol, Flusrilidol, Flusrilidol, Fosetyl sodium, fthalide, fuberidazole, furalaxyl, furametpyr, furcarbonil, furconazole, furconazole-cis,
  • Imazalil Imibenconazol, Iminoctadin, Iminoctadinealbesilat, Iminoctadinetriacetat, Iodocarb, Ipconazol, Iprobefos (IBP), Iprodione, Irumamycin, Isoprothiolan, Isovaledione,
  • Mancopper Mancozeb, Maneb, Meferimzone, Mepanipyrim, Mepronil, Metalaxyl, Metconazol, Methasulfocarb, Methfuroxam, Metiram, Metomeclam, Metsulfovax,
  • Oxadixyl Oxamocarb, Oxolinicacid, Oxycarboxim, Oxyfenthiin,
  • Paclobutrazole pefurazoate, penconazole, pencycuron, phosdiphen, pimaricin, piperalin, polyoxin, polyoxorim, probenazole, prochloraz, procymidone, propamocarb, propanosine sodium, propiconazole, propineb, pyrazophos, pyrifenox. Pyrimethanil, pyroquilon, pyroxyfur,
  • Tebuconazole Tebuconazole, tecloftalam, tecnazene, Tetcyclacis, tetraconazole, thiabendazole, Thicyofen, Thifluzamide, thiophanate-methyl, thiram, Tioxymid, tolclofos-methyl, tolylfluanid, triadimefon, triadimenol, Triazbutil, triazoxide, Trichlamid, tricyclazole, Tridemo ⁇ h, triflumizole, triforine, triticonazole,
  • Fenamiphos Fenazaquin, Fenbutatinoxid, Fenitrothion, Fenobucarb, Fenothiocarb, Fenoxycarb, Fenpropathrin, Fenpyrad, Fenpyroximat, Fenthion, Fenvalerate, Fipronil, Fluazinam, Flucycloxuron, Flucythrinat, Flufenoxuron, Flufenproxatophon, Fufionphonophone, Fufionfox, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fu
  • Parathion A Parathion M, Permethrin, Phenthoat, Phorat, Phosalon, Phosmet, Phosphamidon, Phoxim, Pirimicarb, Pirimiphos M, Pirimiphos A, Profenofos, Promecarb, Propaphos, Propoxur, Prothiofos, Prothoat, Pymethionos, Pyridaphrinin, Pyridaphrinin, Pyridaphrinin Pyrethrum, Pyridaben, Pyrimidifen, Pyriproxifen,
  • Tebufenozid Tebufenpyrad
  • Tebupirimiphos Teflubenzuron, Tefluthrin, Temephos, Terbam, Terbufos, Tetrachlorvinphos, Thiafenox, Thiodicarb, Thiofanox, Thiomethonon, Thionazin, Thuringiensin, Tralathenethronon, Tronomenhrononium, Tronomenhrononium, Tronomenhrononium, Tronomenhrononium, Tronomenhrononium, Tronomenhrononium, Tronomenhrononium, Tronomenhrononium
  • the active compounds according to the invention can also be present in their commercially available formulations and in the use forms prepared from these formulations in a mixture with synergists.
  • Synergists are compounds through which the action of the active ingredients is increased without the added synergist itself having to be active.
  • the active substance content of the use forms prepared from the commercially available formulations can vary within wide ranges.
  • the active substance concentration of the use forms can be from 0.0000001 to 95% by weight of active substance, preferably between 0.0001 and 1% by weight.
  • the application takes place in a customary manner adapted to the application forms.
  • the active ingredient When used against hygiene pests and pests of stored products, the active ingredient is distinguished by an excellent residual action on wood and clay as well as a good stability to alkali on limed substrates.
  • the active compounds according to the invention act not only against plant, hygiene and stored-product pests, but also in the veterinary sector against animal parasites (ectoparasites) such as tick ticks, leather ticks, mites, running mites, flies (stinging and licking), parasitic fly larvae, lice, hair lice, Featherlings and fleas.
  • animal parasites ectoparasites
  • tick ticks leather ticks
  • mites running mites
  • flies stinging and licking
  • parasitic fly larvae lice, hair lice, Featherlings and fleas.
  • Ischnocerina e.g. Trimenopon spp., Menopon spp., Trinoton spp., Bovicola spp., Werneckiella spp., Lepikentron spp., Damalina spp., Trichodectes spp., Felicola spp ..
  • Nematocerina and Brachycerina e.g. Aedes spp., Anopheles spp., Culex spp., Simulium spp., Eusimulium spp., Phlebotomus spp., Lutzomyia spp., Culicoides spp., Chrysops spp., Hybomitra spp., Atylotus spp., Tabanus spp., Haematopota ., Philipomyia spp.,
  • Amblyomma spp. Boophilus spp., Dermacentor spp., Haemophysalis spp., Hyalomma spp., Rhipicephalus spp., Dermanyssus spp., Raillietia spp., Pneumonyssus spp., Sternostoma spp., Varroa spp ..
  • Acarapis spp. Cheyletiella spp., Ornitrocheyletia spp., Myobia spp., Psorergates spp., Demodex spp., Trombicula spp., Listrophorus spp., Acarus spp., Tyrophagus spp., Caloglyphus spp., Hypodterol spp ., Psoroptes spp., Chorioptes spp., Otodectes spp., Sarcoptes spp., Notoedres spp., Knemidocoptes spp., Cytodites spp., Laminosioptes spp ..
  • the active compounds of the formula (I) according to the invention are also suitable for combating arthropods which are agricultural animals such as cattle, sheep, goats, horses, pigs, donkeys, camels, buffalo, rabbits, chickens, turkeys.
  • arthropods are agricultural animals such as cattle, sheep, goats, horses, pigs, donkeys, camels, buffalo, rabbits, chickens, turkeys.
  • Ducks, geese, bees, other domestic animals such as dogs, cats, house birds, aquarium fish and so-called experimental animals such as hamsters, guinea pigs, rats and mice.
  • the active compounds according to the invention are used in the veterinary sector in a known manner by enteral administration in the form of, for example, tablets, capsules, drinkers, drenches, granules, pastes, boluses, the feed-through method, suppositories, by parenteral administration, for example by Injections (intramuscular, subcutaneous, intravenous, intraperitoneal, etc.), implants, through nasal
  • dermal application in the form of, for example, diving or bathing (dipping), spraying (spray), pouring on (pour-on and spot-on), washing, powdering and with the help of shaped articles containing active ingredients, such as collars, ear tags, tail tags , Limb straps, holsters, marking devices etc.
  • active ingredients such as collars, ear tags, tail tags , Limb straps, holsters, marking devices etc.
  • the active compounds of the formula (I) can be used as formulations (for example powders, emulsions, flowable agents) which contain the active compounds in an amount of 1 to 80% by weight, directly or apply after 100 to 10,000-fold dilution or use it as a chemical bath.
  • formulations for example powders, emulsions, flowable agents
  • insects have a high insecticidal action against insects which destroy industrial materials.
  • insects may be mentioned by way of example and preferably, but without limitation:
  • Kalotermes flavicollis Cryptotermes brevis, Heterotermes indicola, Reticulitermes flavipes, Reticulitermes santonensis, Reticulitermes lucifugus, Mastotermes darwiniensis, Zootermopsis nevadensis, Coptotermes formosanus.
  • Bristle tails such as Lepisma saccarina.
  • non-living materials such as preferably plastics, adhesives, glues, papers and cartons, leather, wood and wood processing products and paints.
  • the material to be protected against insect infestation is very particularly preferably wood and wood processing products.
  • Wood and wood processing products which can be protected by the agent according to the invention or mixtures containing it are to be understood as examples: timber, wooden beams, railway sleepers, bridge parts, boat jetties, Wooden vehicles, boxes, pallets, containers, telephone poles, wooden cladding, wooden windows and doors, plywood, chipboard, carpentry or wooden products that are used in general in house construction or joinery.
  • the active compounds can be used as such, in the form of concentrates or generally customary formulations, such as powders, granules, solutions, suspensions, emulsions or pastes.
  • formulations mentioned can be prepared in a manner known per se, e.g. by mixing the active ingredients with at least one solution or
  • insecticidal agents or used to protect wood and wood-based materials
  • Concentrates contain the active ingredient according to the invention in a concentration of 0.0001 to 95% by weight, in particular 0.001 to 60% by weight.
  • the amount of the agents or concentrates used depends on the type and occurrence of the insects and on the medium. The optimal amount can be determined in each case by test series. In general, however, it is sufficient to use 0.0001 to 20% by weight, preferably 0.001 to 10% by weight, of the active compound, based on the material to be protected.
  • organic-chemical solvent or solvent mixture and / or an oily or oily or low-volatility organic-chemical solvent or solvent mixture and / or a polar organic-chemical solvent or solvent mixture and / or water and optionally an emulsifier and / or wetting agents.
  • the organic chemical solvents used are preferably oily or oily solvents with an evaporation number above 35 and a flash point above 30 ° C., preferably above 45 ° C.
  • Corresponding mineral oils or their aromatic fractions or mineral oil-containing solvent mixtures preferably white spirit, petroleum and / or alkylbenzene, are used as such low-volatility, water-insoluble, oily and oily solvents.
  • Mineral oils with a boiling range of 170 to 220 ° C, white spirit with a boiling range of 170 to 220 ° C, spindle oil with a boiling range of 250 to 350 ° C, petroleum or aromatics with a boiling range of 160 to 280 ° C are advantageous.
  • the organic low-volatility oily or oily solvents with an evaporation number above 35 and a flash point above 30 ° C., preferably above 45 ° C. can be partially replaced by slightly or medium-volatile organic chemical solvents, with the proviso that the solvent mixture is also a Evaporation number above 35 and a flash point above 30 ° C, preferably above 45 ° C, and that the insecticide-fungicide mixture is soluble or emulsifiable in this solvent mixture.
  • part of the organic chemical solvent or solvent mixture or an aliphatic polar organic chemical solvent or solvent mixture is replaced.
  • Aliphatic hydroxyl and / or ester and / or ether groups are preferably used organic chemical solvents such as glycol ether, ester or the like - for use.
  • the known water-thinnable synthetic resins and / or synthetic resins which are soluble or dispersible or emulsifiable in the organic chemical solvents used and / or binding drying oils, in particular binders consisting of or containing, are used as organic chemical binders Acrylate resin, a vinyl resin, e.g. Polyvinyl acetate, polyester resin, polycondensation or polyaddition resin, polyurethane resin, alkyd resin or modified alkyd resin, phenolic resin, hydrocarbon resin such as indene-coumarone resin, silicone resin, drying vegetable and / or drying oils and / or physically drying binders based on a natural and / / or synthetic resin used.
  • a vinyl resin e.g. Polyvinyl acetate, polyester resin, polycondensation or polyaddition resin, polyurethane resin, alkyd resin or modified alkyd resin, phenolic resin, hydrocarbon resin such as indene-coumarone resin, silicone resin, drying vegetable
  • the synthetic resin used as a binder can be used in the form of an emulsion, dispersion or solution. Bitumen or bituminous substances up to 10% by weight can also be used as binders. In addition, known dyes, pigments, water-repellants, odor correctors and inhibitors or anticorrosive agents and the like can be used.
  • At least one alkyd resin or modified alkyd resin and / or a drying vegetable oil is preferably contained in the agent or in the concentrate as the organic chemical binder.
  • Alkyd resins with an oil content of more than 45% by weight, preferably 50 to 68% by weight, are preferably used according to the invention.
  • binder All or part of the binder mentioned can be replaced by a fixative (mixture) or a plasticizer (mixture). These additives are intended to prevent volatilization of the active ingredients and crystallization or precipitation. They preferably replace 0.01 to 30% of the binder (based on
  • the plasticizers come from the chemical classes of phthalic acid esters such as dibutyl, dioctyl or benzyl butyl phthalate, phosphoric acid esters such as tributyl phosphate, adipic acid esters such as di- (2-ethylhexyl) adipate, stearates such as butyl stearate or amyl stearate, oleates such as butyl oleate or higher molecular glycerol ether, glycerol ether, glycerol ether, glycerol ether, glycerol ether, glycerol ether, glycerol ether, glycerol ether, glycerol ether, glycerol ether, glycerol ether - ether, glycerol ester and p-toluenesulfonic acid ester.
  • phthalic acid esters such as dibut
  • Fixing agents are chemically based on polyvinyl alkyl ethers such as e.g. Polyvinyl methyl ether or ketones such as benzophenone, ethylene benzophenone.
  • Water is also particularly suitable as a solvent or diluent, if appropriate in a mixture with one or more of the above-mentioned organic chemical solvents or diluents, emulsifiers and dispersants.
  • a particularly effective wood protection is achieved through industrial impregnation processes, e.g. Vacuum. Double vacuum or printing process.
  • the ready-to-use compositions can optionally contain further insecticides and, if appropriate, one or more fungicides.
  • the insecticides and fungicides mentioned in Wo 94/29 268 are particularly suitable as additional mixing partners.
  • the compounds mentioned in this document are an integral part of the present application.
  • Insecticides such as chlorpyriphos, phoxime, silafluofin, alphamethrin, cyfluthrin, cypermethrin, deltamethrin, permethrin, imidacloprid, NI-25, flufenoxuron, hexaflumuron and triflumuron can be used as very particularly preferred mixing partners.
  • fungicides such as epoxyconazole, hexaconazole, azaconazole, propiconazole, tebuconazole, cyproconazole, metconazole, imazalil, dichlorfluanide.
  • Solvent 7 parts by weight of dimethylformamide emulsifier: 1 part by weight of alkylaryl polyglycol ether
  • active compound 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration.
  • Cabbage leaves (Brassica oleracea), which are heavily infested with the peach aphid (Mycus persicae), are dipped into the active ingredient preparation of the desired
  • the kill is determined in%. 100% means that all aphids have been killed; 0% means that no aphids have been killed.
  • Example B At an exemplary active ingredient concentration of 0.1%, for example the compound of preparation example 1 showed a kill of 90% and the compounds of preparation examples 2 and 8 showed a kill of 100%, in each case after 6 days.
  • Example B At an exemplary active ingredient concentration of 0.1%, for example the compound of preparation example 1 showed a kill of 90% and the compounds of preparation examples 2 and 8 showed a kill of 100%, in each case after 6 days.
  • Emulsifier 1 part by weight of alkylaryl polyglycol ether
  • active compound 1 part by weight of active compound is mixed with the stated amount of solvent and the given amount of emulsifier, and the concentrate is diluted with water to the desired concentration.
  • Cabbage leaves (Brassica oleracea) are treated by being dipped into the preparation of active compound of the desired concentration and populated with caterpillars of the army worm (Spodoptera frugiperda) while the leaves are still moist.
  • the kill is determined in%. 100% means that all caterpillars have been killed; 0% means that no caterpillars have been killed.
  • the compound of preparation example 2 with an exemplary active compound concentration of 0.1%, showed a kill of 85% after 7 days.
  • Test animals adult Musca domestica, strain Reichswald (OP, SP, carbamate-resistant) solvent: dimethyl sulfoxide
  • the effectiveness of the active ingredient preparation is determined. 100% means that all flies have been killed; 0% means that no flies have been killed.
  • the compound of preparation example 2 showed a 100% action at an exemplary active ingredient concentration of 100 ppm.
  • Test animals Lucilia cuprina larvae
  • test tube which contains approx. 1 cm 3 horse meat and 0.5 ml of the active ingredient preparation.
  • the effectiveness of the active substance preparation is determined after 24 and 48 hours.
  • the test tubes are transferred to beakers with a sand-covered bottom. After a further 2 days, the test tubes are removed and the dolls are counted.
  • the effect of the preparation of active substance is assessed according to the number of flies hatched after 1.5 times the development time of an untreated control. 100% means that no flies have hatched; 0% means that all flies hatched normally.
  • Test animals adult sucked females
  • the compound of preparation example 1 showed a 100% action at an exemplary active ingredient concentration of 100 ppm.
  • Test animals adult sucked females
  • the test is carried out in 5-fold determination, 1 ⁇ l of the solutions is injected into the abdomen, the animals are transferred into dishes and stored in an air-conditioned room.
  • the effectiveness check is carried out after 7 days on the inhibition of egg laying. An effect of 100% means that no tick has laid eggs.
  • the compounds of Preparation Examples 1 and 2 showed a 100% activity at an exemplary active ingredient concentration of 20 ⁇ g / animal.
  • Test animals adults of Ctenocephalides felis
  • a suitable active ingredient solution is prepared from 20 mg of active ingredient with 1 ml of DMSO. 15 ⁇ l of this formulation are added to 3 ml of citrated cattle blood and stirred.
  • Fleas can be absorbed through the parafilm membrane. While the blood is being heated to 37 ° C, a temperature of 25 ° C is set in the area of the flea chambers. Controls are mixed with the same volume of DMSO without the addition of a compound. Triple determinations are carried out.
  • Example H the compound of preparation example 2 showed a 100% action at an exemplary active ingredient concentration of 100 ppm.
  • Emulsifier 1 part by weight of alkylaryl polyglycol ether
  • Cabbage leaves (Brassica oleracea) are treated by being dipped into the preparation of active compound of the desired concentration and populated with larvae of the horseradish beetle (Phaedon cochleariae) while the leaves are still moist.
  • the kill is determined in%. 100% means that all caterpillars have been killed; 0% means that no caterpillars have been killed.

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Abstract

The invention relates to novel substituted 3-thiocarbamoylpyrazoles of general formula (I), wherein m, n, R<1>, R<2>, R<3> and Ar have the meanings cited in the description. The invention further relates to methods for the production and use thereof as pesticides.

Description

Substituierte 3-ThiocarbamoylpyrazoleSubstituted 3-thiocarbamoylpyrazoles
Die Erfindung betrifft neue substituierte 3-Thiocarbamoylpyrazole, mehrere Verfah- ren zu ihrer Herstellung und ihre Verwendung als Schädlingsbekämpfungsmittel.The invention relates to new substituted 3-thiocarbamoylpyrazoles, several processes for their preparation and their use as pesticides.
Es ist bereits bekannt, daß verschiedene substituierte Aminopyrazole eine gute Wirksamkeit gegen Schädlinge besitzen (vgl. z.B. WO 97/22 593, WO 97/44 340, EP 295 117, EP 807 668, EP 738 713, EP 352 944, EP 201 852, EP 418 016. EP 659 745, US 5 688 966, US 5 631 381, US 5 629 335). Die Wirkhöhe und/oderIt is already known that various substituted aminopyrazoles have good activity against pests (see, for example, WO 97/22 593, WO 97/44 340, EP 295 117, EP 807 668, EP 738 713, EP 352 944, EP 201 852 , EP 418 016. EP 659 745, US 5 688 966, US 5 631 381, US 5 629 335). The effective height and / or
Wirkungsdauer der vorbekannten Verbindungen ist jedoch, insbesondere bei bestimmten Schädlingen und/oder bei niedrigen Anwendungskonzentrationen nicht in allen Anwendungsgebieten völlig zufriedenstellend.However, the duration of action of the known compounds is not entirely satisfactory in all areas of application, in particular in the case of certain pests and / or at low application concentrations.
Es wurden neue substituierte 3-Thiocarbamoylpyrazole der allgemeinen Formel (I) gefunden,New substituted 3-thiocarbamoylpyrazoles of the general formula (I) have been found
in welcher in which
R1 für H2N-CS- steht,R 1 stands for H 2 N-CS-,
m für die Zahlen 0 oder 1 steht,m represents the numbers 0 or 1,
für die Zahlen 0, 1 oder 2 steht, R2 für Alkyl, Alkenyl, Alkinyl, Cyanalkyl, Thiocyanatoalkyl, Nitroalkyl, Alkyl- - thioalkyl, Alkylsulfinylalkyl, Alkylsulfonylalkyl, Halogenalkylthioalkyl, Halogenalkylsulfinylalkyl, Halogenalkylsulfonylalkyl, Alkenylthioalkyl, Alkenylsulfinylalkyl, Alkenylsulfonylalkyl. Alkinylthioalkyl, Alkinylsul- finylalkyl, Alkinylsulfonylalkyl, Alkoxycarbonylalkyl, Halogenalkoxy- carbonylalkyl, Alkoxycarbonyl, Alkenyloxycarbonyl, Halogenalkoxy- carbonyl, Alkylcarbonyl, Alkoxyallkyl, Halogenalkoxyalkyl, Alkoxyal- kylthioalkyl, Alkoxy alkylsulfinylalkyl, Alkoxyalkylsulfonylalkyl, Halogenal- koxyalkylthioalkyl, Halogenalkoxyalkylsulfinylalkyl, Halogenalkoxyalkyl- sulfonylalkyl, Alkylaminoalkyl, Dialkylaminoalkyl, Trialkylsilylalkyl; jeweils gegebenenfalls substituiertes Cycloalkyl, Cycloalkenyl oder Cycloal- kylalkyl; sowie für jeweils gegebenenfalls im Arylteil bzw. Heteroarylteil substituiertesrepresents the numbers 0, 1 or 2, R 2 for alkyl, alkenyl, alkynyl, cyanoalkyl, thiocyanatoalkyl, nitroalkyl, alkyl - thioalkyl, alkylsulfinylalkyl, alkylsulfonylalkyl, haloalkylthioalkyl, haloalkylsulfinylalkyl, haloalkylsulfonylalkyl, alkenylthioalkyl, alkenylsulfinylalkyl, alkenylsulfonylalkyl. Alkynylthioalkyl, alkynylsulfinylalkyl, alkynylsulfonylalkyl, alkoxycarbonylalkyl, haloalkoxycarbonylalkyl, alkoxycarbonyl, alkenyloxycarbonyl, haloalkoxycarbonyl, alkylcarbonyl, alkoxyallkyl, haloalkoxyalkyl, alkoxyalkylthioalkyl, alkoxyalkylsulfinylalkyl, alkoxyalkylalkyloxyalkyl, alkoxyalkylalkyloxyalkyloxy, alkoxyalkylalkyloxyalkyloxy, alkoxyalkylalkyloxyalkyloxy, alkoxyalkylalkyloxyalkyloxy, alkoxyalkylalkyloxyalkyloxy, alkoxyalkylalkyloxyalkyloxy, alkoxyalkylalkyloxyalkyloxy, alkoxyalkylalkyloxyalkyloxy, alkoxyalkylalkyloxyalkyl, alkoxyalkylalkyloxyalkyloxy, alkoxyalkylalkylalkylalkyl, alkoxyalkylalkylalkylalkyl, alkoxyalkylalkyloxyalkyloxy, alkoxyalkyl alkoxyalkyl, alkoxy alkyl alkoxy alkyl, alkoxy alkyl alkoxy alkyl, , Trialkylsilylalkyl; each optionally substituted cycloalkyl, cycloalkenyl or cycloalkylalkyl; and for each optionally substituted in the aryl part or heteroaryl part
Aryl, Heteroaryl, Arylalkyl, Heteroarylalkyl, Aryloxyalkyl, Arylthioalkyl, Arylsulfmylalkyl, Arylsulfonylalkyl, Arylalkyloxyalkyl, Arylalkylthioalkyl,Aryl, heteroaryl, arylalkyl, heteroarylalkyl, aryloxyalkyl, arylthioalkyl, arylsulfmylalkyl, arylsulfonylalkyl, arylalkyloxyalkyl, arylalkylthioalkyl,
Arylalkylsulfinylalkyl oder Arylalkylsulfonylalkyl steht,Arylalkylsulfinylalkyl or arylalkylsulfonylalkyl,
R2 für die Bedeutung von m = 0 zusätzlich für Thiocyanato, Halogen, Nitro,R 2 for the meaning of m = 0 additionally for thiocyanato, halogen, nitro,
Cyano, Hydroxy, Halogenalkyl, Halogenalkenyl, Chlorsulfonyl, Alkoxy, Halogenalkoxy, Alkenyloxy, Halogenalkenyloxy, Alkylcarbonyloxy, Formyl,Cyano, hydroxy, haloalkyl, haloalkenyl, chlorosulfonyl, alkoxy, haloalkoxy, alkenyloxy, haloalkenyloxy, alkylcarbonyloxy, formyl,
Trialkylsilylethinyl, gegebenenfalls substituiertes Aryloxy oder für eine der folgenden Gruppierungen steht:Trialkylsilylethinyl, optionally substituted aryloxy or for one of the following groups:
-NHR4, -NR4R5, -NHNH2, -CONH2, -CSNH2, -CONR R5, -SO2NR4R5, -CR6=NOR7, -CH(OH)R8 oder -CH(CN)OR9,-NHR 4 , -NR 4 R 5 , -NHNH 2 , -CONH 2 , -CSNH 2 , -CONR R 5 , -SO 2 NR 4 R 5 , -CR 6 = NOR 7 , -CH (OH) R 8 or -CH (CN) OR9,
wobeiin which
R4 und R5 unabhängig voneinander für Wasserstoff, Cyano, Alkyl oder jeweils gegebenenfalls substituiertes Aryl oder Aralkyl stehen, R6 für Wasserstoff oder Alkyl steht,R 4 and R 5 independently of one another represent hydrogen, cyano, alkyl or in each case optionally substituted aryl or aralkyl, R 6 represents hydrogen or alkyl,
R7 für Wasserstoff, Alkyl oder gegebenenfalls substituiertes Aralkyl steht,R 7 represents hydrogen, alkyl or optionally substituted aralkyl,
R8 für Alkyl oder Halogenalkyl steht undR 8 represents alkyl or haloalkyl and
R9 für Alkyl steht,R 9 represents alkyl,
für Wasserstoff, Amino, Halogen oder für eine der folgenden Gruppierungen steht:represents hydrogen, amino, halogen or one of the following groups:
-NH-CO-R10, -NHR1 1, -OR12, -SR12 oder -NR13-CX-C(R14, R^, Rl6)-NH-CO-R 10 , -NHR 1 1 , -OR 12 , -SR 12 or -NR 13 -CX-C (R 14 , R ^, Rl6)
wobeiin which
R10 für Alkyl, Halogenalkyl, Alkoxyalkyl oder jeweils gegebenenfalls substituiertes Phenyl, Phenoxy oder Pyridyl steht,R 10 represents alkyl, haloalkyl, alkoxyalkyl or in each case optionally substituted phenyl, phenoxy or pyridyl,
R1 1 für Alkyl, Alkenyl, Alkinyl, Formyl, Alkylcarbonyl, Halogenalkyl- carbonyl oder Alkoxycarbonyl steht,R 1 1 represents alkyl, alkenyl, alkynyl, formyl, alkylcarbonyl, haloalkylcarbonyl or alkoxycarbonyl,
R12 für Alkyl, Alkenyl, Alkinyl, gegebenenfalls substituiertes Aralkyl, Dialkylaminoalkyl oder für die Gruppierung -P(=Y)(OR17)(SR18) steht,R 12 represents alkyl, alkenyl, alkynyl, optionally substituted aralkyl, dialkylaminoalkyl or the grouping -P (= Y) (OR 17 ) (SR 18 ),
wobeiin which
R17 und R18 unabhängig voneinander für Alkyl stehen undR 17 and R 18 are independently alkyl and
Y für Sauerstoff oder Schwefel steht, R13 für Wasserstoff, Alkyl, Alkoxyalkyl, Propargyl, Allyl, Alkoxy- carbonyl, Alkylcarbonyl, gegebenenfalls substituiertes Benzyl oder die Gruppierung -CO-C(R14, R15, R16) steht,Y represents oxygen or sulfur, R 13 represents hydrogen, alkyl, alkoxyalkyl, propargyl, allyl, alkoxycarbonyl, alkylcarbonyl, optionally substituted benzyl or the grouping -CO-C (R 14 , R 15 , R 16 ),
R14 für Wasserstoff, Alkyl, Halogenalkyl, Halogen oder gegebenenfalls substituiertes Phenyl steht undR 14 represents hydrogen, alkyl, haloalkyl, halogen or optionally substituted phenyl and
R15 für Wasserstoff, Alkyl, Halogenalkyl, Halogen, Halalkoxyalkyl, Alkylthioalkyl, Alkylsulfinylalkyl, Alkylsulfonylalkyl, Alkoxy(al- koxy)ralkyl mit r = 0 bis 4, Hydroxy, Alkoxycarbonylalkyl oder Alkoxy steht, oderR 15 represents hydrogen, alkyl, haloalkyl, halogen, halalkoxyalkyl, alkylthioalkyl, alkylsulfinylalkyl, alkylsulfonylalkyl, alkoxy (alkoxy) r alkyl with r = 0 to 4, hydroxyl, alkoxycarbonylalkyl or alkoxy, or
R14 und R15 gemeinsam mit dem Kohlenstoffatom, an das sie gebunden sind, für ein 3- bis 7-gliedriges Ringsystem mit gegebenenfalls bis zu zweiR 14 and R 15 together with the carbon atom to which they are attached, for a 3- to 7-membered ring system with optionally up to two
Heteroatomen stehen undHeteroatoms stand and
R16 für Hydroxy, Alkoxy, Halalkoxy, Alkoxy(alkoxy)p mit p= 1 bis 4 oder Halalkoxy(alkoxy)q mit q = 1 bis 4 steht, undR 16 stands for hydroxy, alkoxy, halalkoxy, alkoxy (alkoxy) p with p = 1 to 4 or halalkoxy (alkoxy) q with q = 1 to 4, and
X für Sauerstoff oder Schwefel steht, undX represents oxygen or sulfur, and
Ar für jeweils gegebenenfalls substituiertes Phenyl oder Pyridyl steht.Ar stands for optionally substituted phenyl or pyridyl.
Weiterhin wurde gefunden, daß man die neuen substituierten 3-Thiocarbamoylpyra- zole der Formel (I) erhält, wenn manFurthermore, it was found that the new substituted 3-thiocarbamoylpyrazoles of the formula (I) can be obtained if
a) 3-Cyanopyrazol-Derivate der Formel (II) a) 3-cyanopyrazole derivatives of the formula (II)
in welcherin which
Ar, R2, R3, m und n die oben angegebene Bedeutung haben,Ar, R 2 , R 3 , m and n have the meaning given above,
mit Schwefelwasserstoff, gegebenenfalls in Gegenwart eines Reaktionshilfsmittels und gegebenenfalls in Gegenwart eines Verdünnungsmittels umsetzt;with hydrogen sulfide, optionally in the presence of a reaction auxiliary and optionally in the presence of a diluent;
oderor
b) 3-Thiocarbamoylpyrazol-Derivate der Formel (III)b) 3-thiocarbamoylpyrazole derivatives of the formula (III)
in welcherin which
Ar die oben angegebene Bedeutung hat undAr has the meaning given above and
R3"1 für eine der folgenden Gruppierungen steht: -NHR11 , -OR12 oder -NR13-CX-C(R14, R15, R16), R 3 " 1 represents one of the following groupings: -NHR11, -OR12 or -NR13-CX-C (R14, R15, R16),
wobeiin which
R10 bis R16 und X die oben angegebene Bedeutung haben,R 10 to R 16 and X have the meaning given above,
mit Sulfenylhalogeniden der Formel (IV)with sulfenyl halides of the formula (IV)
Hal-S-R2 (IV)Hal-SR 2 (IV)
in welcherin which
R2 die oben angegebene Bedeutung hat undR 2 has the meaning given above and
Hai für Halogen, insbesondere Chlor oder Brom steht,Shark represents halogen, especially chlorine or bromine,
gegebenenfalls in Gegenwart eines Verdünnungsmittels und gegebenenfalls in Gegenwart eines Reaktionshilfsmittels umsetzt;if appropriate in the presence of a diluent and if appropriate in the presence of a reaction auxiliary;
oderor
c) die gemäß den Verfahren (a) oder (b) erhältlichen 3-Thiocarbamoylpyrazol-c) the 3-thiocarbamoylpyrazole obtainable according to processes (a) or (b)
Derivate der Formel (Ia)Derivatives of the formula (Ia)
in welcher in which
Ar, R2 und R3 die oben angegebene Bedeutung haben,Ar, R 2 and R 3 have the meaning given above,
mit Oxidationsmitteln gegebenenfalls in Gegenwart eines Verdünnungsmittels und gegebenenfalls in Gegenwart eines Katalysators oxidiert.oxidized with oxidizing agents optionally in the presence of a diluent and optionally in the presence of a catalyst.
Schließlich wurde gefunden, daß die neuen 3-Thiocarbamoylpyrazol-Derivate der Formel (I) stark ausgeprägte biologische Eigenschaften besitzen und vor allem zurFinally, it was found that the new 3-thiocarbamoylpyrazole derivatives of the formula (I) have highly pronounced biological properties and especially for
Bekämpfung von tierischen Schädlingen, insbesondere von Insekten, Spinnentieren und Nematoden, die in der Landwirtschaft, in Forsten, im Vorrats- und Materialschutz sowie auf dem Hygienesektor vorkommen, geeignet sind.Control of animal pests, in particular insects, arachnids and nematodes, which are found in agriculture, in forests, in the protection of stored goods and materials and in the hygiene sector.
Die erfindungsgemäßen Verbindungen sind durch die Formel (I) allgemein definiert.The compounds according to the invention are generally defined by the formula (I).
Bevorzugte Substituenten bzw. Bereiche der in den oben und nachstehend erwähnten Formeln aufgeführten Reste werden im folgenden erläutert.Preferred substituents or ranges of the radicals listed in the formulas mentioned above and below are explained below.
R2 steht bevorzugt für (CrC6)-Alkyl, (C2-C6)-Alkenyl, (C2-C6)-Alkinyl, Cyan-R 2 preferably represents (C r C 6 ) alkyl, (C 2 -C 6 ) alkenyl, (C 2 -C 6 ) alkynyl, cyano-
(CrC4)-alkyl, Thiocyanato-(CrC4)-alkyl, Nitro-(C,-C4)-alkyl, (C,-C6)- Alkylthio-(C , -C4)-alkyl, (C , -C6)-Alkylsulfιnyl-(C , -C4)-alky 1, (C , -C6)- Alkylsulfonyl-(CrC4)-alkyl, (CrC4)-Halogenalkylthio-(CrC4)-alkyl mit 1 bis 6 Halogenatomen, (C1-C )-Halogenalkylsulfιnyl-(CrC4)-alkyl mit 1 bis 6 Halogenatomen, (C1-C4)-Halogenalkylsulfonyl-(C1-C )-alkyl mit 1 bis 6(C r C 4 ) -alkyl, thiocyanato- (C r C 4 ) -alkyl, nitro- (C, -C 4 ) -alkyl, (C, -C 6 ) - alkylthio- (C, -C 4 ) - alkyl, (C, -C 6 ) alkylsulfonyl (C, -C 4 ) alkyl 1, (C, -C 6 ) alkylsulfonyl (C r C 4 ) alkyl, (C r C 4 ) haloalkylthio - (C r C 4 ) alkyl with 1 to 6 halogen atoms, (C 1 -C) haloalkylsulfionyl- (C r C 4 ) alkyl with 1 to 6 halogen atoms, (C 1 -C 4 ) haloalkylsulfonyl- (C 1 -C) alkyl with 1 to 6
Halogenatomen, (C2-C6)-Alkenylthio-(C . -C4)-alky 1, (C2-C6)- Alkenylsul- fιnyl-(C , -C4)-alkyl, (C2-C6)-Alkenylsulfonyl-(C i -C4)-alkyl, (C2-C6)- Alkinylthio-(C < -C4)alkyl, (C2-C6)-Alkinylsulfιnyl-(C , -C4)alkyl, (C2-C6)- Alkinylsulfonyl-(C , -C4)alky 1, (C , -C4)- Alkoxy-carbony 1-(C , -C4)-alkyl, (C , - C4)-Halogenalkoxy-carbonyl-(C]-C4)-alkyl mit 1 bis 5 Halogenatomen, (C C6)- Alkoxy-carbony 1, (C l -C6)- Alky 1-carbonyl, (C , -C6)- Alkoxy-(C , -C4)- alkyl, (CrC6)-Halogenalkoxy-(CrC )-alkyl mit 1 bis 6 Halogenatomen, (Cr C4)-Alkoxy-(C 1 -C4)-alkylthio-(C , -C4)-alkyl, (C l -C4)-Alkoxy-(C , -C4)-alky 1- sulfιnyl-(C , -C4)-alkyl, Alkoxy-(C , -C4)-alkylsulfonyl-(C l -C4)-alkyl, (C , - C4)-Halogenalkoxy-(CrC4)-alkylthio-(CrC4)-alkyl mit 1 bis 5 Halogenatomen, (C1-C4)-Halogenalkoxy-(C]-C4)-alkylsulfιnyl-(C1-C4)-alkyl mit 1 bis 5 Halogenatomen, (C i -C4)-Halogenalkoxy-(C j -C4)-alkylsulfonyl-(C j -C4)- alkyl mit 1 bis 5 Halogenatomen, (Cj-C4)-Alkylamino-(C]-C4)-alkyl, Di-(Cr C4)-alkylamino-(C , -C4)-alkyl, Tri-(C , -C4)-alkylsilyl-(C i -C4)-alkyl; für jeweils gegebenenfalls einfach bis fünffach, gleich oder verschieden substituiertes (C3-C6)-Cycloalkyl, (C5-C6)-Cycloalkenyl oder (C3-C6)-Cycloal- kyl-(C]-C2)-alkyl, wobei als Substituenten genannt seien: (CrC4)- Alkyl, (CrC4)-Alkoxy, Halogen, (CrC4)-Halogenalkyl mit 1 bis 5 Halogenatomen und (Cj-C4)-Halogenalkoxy mit 1 bis 5 Halogenatomen; sowie für jeweils gegebenenfalls einfach bis dreifach, gleich oder verschieden substituiertes Phenyl, Phenyl-(CrC2)-alkyl, Phenoxy-(CrC2)-alkyl, Phe- nylthio-(C , -C2)-alky 1, Phenylsulfιnyl-(C , -C2)-alky 1, Pheny lsulfonyl-(C , -C2)- alkyl, Phenyl-(C λ -C2)-alkyloxy-(C , -C2)-alkyl, Pheny 1-(C , -C2)-alkylthio-(C , - C2)-alkyl, Phenyl-(C j -C2)-alky lsulfmy 1-(C , -C2)-alky 1, Pheny 1-(C x -C2)-alky 1- sulfonyl-(CrC2)-alkyl, Pyridyl oder Pyridyl-(CrC2)-alkyl, wobei als Phenyl- oder Pyridylsubstituenten genannt seien:Halogen atoms, (C 2 -C 6 ) alkenylthio- (C. -C 4 ) alkyl 1, (C 2 -C 6 ) - alkenylsul- fιnyl- (C, -C 4 ) alkyl, (C 2 -C 6 ) -Alkenylsulfonyl- (C i -C 4 ) alkyl, (C 2 -C 6 ) - alkynylthio- (C <-C 4 ) alkyl, (C 2 -C 6 ) alkynylsulfionyl- (C, -C 4 ) alkyl, (C 2 -C 6 ) - alkynylsulfonyl- (C, -C 4 ) alky 1, (C, -C 4 ) - alkoxy-carbony 1- (C, -C 4 ) -alkyl, (C, - C 4 ) -Halogenalkoxy-carbonyl- (C] -C 4 ) -alkyl with 1 to 5 halogen atoms, (C C 6 ) -alkoxy-carbonyl 1, (C 1 -C 6 ) -alkyl 1-carbonyl, (C, -C 6 ) -alkoxy- (C, -C 4 ) -alkyl, (C r C 6 ) -haloalkoxy - (C r C) -alkyl with 1 to 6 halogen atoms, (C r C 4 ) -alkoxy- (C 1 -C 4 ) -alkylthio- (C, -C 4 ) -alkyl, (C l -C 4 ) -Alkoxy- (C, -C 4 ) -alkyl 1- sulfιnyl- (C, -C 4 ) -alkyl, alkoxy- (C, -C 4 ) -alkylsulfonyl- (C 1 -C 4 ) -alkyl, (C , - C 4 ) -Halogenalkoxy- (C r C 4 ) -alkylthio- (C r C 4 ) -alkyl with 1 to 5 halogen atoms, (C 1 -C 4 ) -Halogenalkoxy- (C] -C 4 ) -alkylsulfιnyl - (C 1 -C 4 ) -alkyl having 1 to 5 halogen atoms, (C i -C 4 ) -haloalkoxy- (C j -C 4 ) -alkylsulfonyl- (C j -C 4 ) -alkyl having 1 to 5 halogen atoms , (Cj-C 4 ) -alkylamino- (C ] -C 4 ) -alkyl, di- (C r C 4 ) -alkylamino- (C, -C 4 ) -alkyl, tri- (C, -C 4 ) -alkylsilyl- (C i -C 4 ) alkyl; for each optionally mono- to pentasubstituted, identically or differently substituted (C 3 -C 6 ) -cycloalkyl, (C 5 -C 6 ) -cycloalkenyl or (C 3 -C 6 ) -cycloalkyl- (C ] -C 2 ) -alkyl, where the following may be mentioned as substituents: (C r C 4 ) -alkyl, (C r C 4 ) -alkoxy, halogen, (C r C 4 ) -haloalkyl having 1 to 5 halogen atoms and (C j -C 4 ) -Halogenalkoxy with 1 to 5 halogen atoms; as well as for phenyl, phenyl- (C r C 2 ) -alkyl, phenoxy- (C r C 2 ) -alkyl, phenylthio- (C, -C 2 ) -alkyl 1, which are optionally mono- to trisubstituted by identical or different substituents , Phenylsulfιnyl- (C, -C 2 ) alkyl 1, Pheny lsulfonyl- (C, -C 2 ) alkyl, phenyl (C λ -C 2 ) alkyloxy- (C, -C 2 ) alkyl, pheny 1- (C, -C 2 ) alkylthio- (C, - C 2 ) alkyl, phenyl- (C j -C 2 ) alkylsulfmy 1- (C, -C 2 ) alkyl 1, pheny 1- (C x -C 2 ) alkyl 1-sulfonyl- (C r C 2 ) -alkyl, pyridyl or pyridyl- (C r C 2 ) -alkyl, where the following may be mentioned as phenyl or pyridyl substituents:
Halogen, (CrC6)- Alkyl, (C2-C6)- Alkenyl, (CrC6)-Alkoxy. (C2-C6)-Alke- nyloxy, (C,-C4)-Alkylthio, (C,-C4)- Alky lsulfmy 1, (CrC4)-Alkylsulfonyl; (CrC6)-Halogenalkyl, (C2-C4)-Halogenalkenyl, (C]-C4)-Halogenalkoxy, (CrC4)-Halogenalkylthio, (CrC4)-Halogenalkylsulfmyl und (C,-C4)-Halo- genalkylsulfonyl mit jeweils 1 bis 5 Halogenatomen; Cyano, Nitro, Hydroxy, Hydrazino, (CrC6)-Dialkylhydrazino, Amino, (CrC6)-Alkylamino, Di-(Cr C6)-alkylamino, (C C6)-Alkylimino, (CrC4)-Alkyl-carbonyl, (CrC4)- Alkyl-carbonyloxy, jeweils gegebenenfalls einfach bis dreifach, gleich oder verschieden durch Halogen, (Cj-C )- Alkyl, (CrC4)-Halogenalkyl mit 1 bis 5Halogen, (C r C 6 ) alkyl, (C 2 -C 6 ) alkenyl, (C r C 6 ) alkoxy. (C 2 -C 6 ) alkynyloxy, (C, -C 4 ) alkylthio, (C, -C 4 ) alkylsulfmy 1, (C r C 4 ) alkylsulfonyl; (C r C 6 ) haloalkyl, (C 2 -C 4 ) haloalkenyl, (C ] -C 4 ) haloalkoxy, (C r C 4 ) haloalkylthio, (C r C 4 ) haloalkylsulfmyl and (C, -C 4 ) -Halogenated alkyl sulfonyl, each with 1 to 5 halogen atoms; Cyano, nitro, hydroxy, hydrazino, (C r C 6 ) dialkyl hydrazino, amino, (C r C 6 ) alkylamino, di (C r C 6 ) alkylamino, (CC 6 ) alkylimino, (C r C 4) -alkyl-carbonyl, (C r C4) - alkyl-carbonyloxy, in each case optionally mono- to trisubstituted by identical or different halogen, (Cj-C) - alkyl, (C r C4) -halogenoalkyl having 1 to 5
Halogenatomen, (C]-C4)-Alkoxy oder (C j -C )-Halogenalkoxy und (C]-C4)- Halogenalkylthio mit jeweils 1 bis 5 Halogenatomen substituiertes Phenyf oder Phenoxy, SF5 Halogen atoms, (C] -C 4 ) alkoxy or (C j -C) haloalkoxy and (C ] -C 4 ) - Haloalkylthio with 1 to 5 halogen atoms each substituted phenyf or phenoxy, SF 5
oder die Gruppierung or the grouping
wobeiin which
R' und R" unabhängig voneinander für Wasserstoff oder (CrC6)-Alkyl stehen undR 'and R "independently of one another represent hydrogen or (C r C 6 ) -alkyl and
Z für -CO oder -SO2 steht.Z represents -CO or -SO 2 .
steht für die Bedeutung von m = 0 zusätzlich vorzugsweise für Thiocyanato, Chlor, Brom, Jod, Nitro, Cyano, Hydroxy, Chlorsulfonyl, (CrC4)- Alkoxy, (C2-C4)-Alkenyloxy; (CrC4)-Halogenalkyl, (C2-C4)-Halogenalkenyl, (Cr stands for the meaning of m = 0 additionally preferably for thiocyanato, chlorine, bromine, iodine, nitro, cyano, hydroxy, chlorosulfonyl, (C r C 4 ) alkoxy, (C 2 -C 4 ) alkenyloxy; (C r C 4 ) haloalkyl, (C 2 -C 4 ) haloalkenyl, (C r
C4)-Halogenalkoxy und (C2-C4)-Halogenalkenyloxy mit jeweils 1 bis 5 Halogenatomen; (CrC4)-Alkyl-carbonyloxy. Formyl, Tri-(CrC4)-alkylsilyl- ethinyl; für gegebenenfalls einfach bis fünffach, gleich oder verschieden substituiertes Phenoxy, wobei als Substituenten die oben für R2 bereits genann- ten Phenylsubstituenten infrage kommen; sowie vorzugsweise für eine der folgenden Gruppierungen:C 4 ) haloalkoxy and (C 2 -C 4 ) haloalkenyloxy each having 1 to 5 halogen atoms; (C r C 4 ) alkyl carbonyloxy. Formyl, tri (C r C 4 ) alkylsilylethynyl; for optionally mono- to pentasubstituted, identically or differently substituted phenoxy, the phenyl substituents already mentioned above for R 2 being suitable as substituents; and preferably for one of the following groups:
-NHR4, -NR4R5, -NHNH2, -CONH2, -CSNH2, -CONR R5, -SO2NR4R5, -CR6=NOR7, -CH(OH)R8 oder -CH(CN)OR9,-NHR 4 , -NR 4 R 5 , -NHNH 2 , -CONH 2 , -CSNH 2 , -CONR R 5 , -SO 2 NR 4 R 5 , -CR 6 = NOR 7 , -CH (OH) R 8 or -CH (CN) OR9,
wobeiin which
R4 und R5 unabhängig voneinander vorzugsweise für Wasserstoff, Cyano, (C,-C4)- Alkyl oder für jeweils gegebenenfalls einfach bis fünffach, gleich oder verschieden substituiertes Phenyl oder Benzyl stehen, wobei als Substituenten die oben für R2 bereits genannten Phenylsub- stituenten infrage kommen.R 4 and R 5 are, independently of one another, preferably for hydrogen, cyano, (C, -C 4 ) alkyl or for in each case optionally up to five times, the same or different substituted phenyl or benzyl, where the phenyl substituents already mentioned above for R 2 are suitable as substituents.
R6 vorzugsweise für Wasserstoff oder (C i -C )- Alkyl steht.R 6 preferably represents hydrogen or (C i -C) alkyl.
R7 vorzugsweise für Wasserstoff (CrC4)- Alkyl oder gegebenenfalls einfach bis fünffach, gleich oder verschieden substituiertes Benzyl steht, wobei als Substituenten die oben für R2 bereits genannten Phenylsub- stituenten infrage kommen.R 7 preferably represents hydrogen (C r C 4 ) alkyl or optionally mono- to pentasubstituted, identically or differently substituted benzyl, the phenyl substituents already mentioned above for R 2 being suitable as substituents.
R8 vorzugsweise für (CrC4)-Alkyl oder (CrC4)-Halogenalkyl mit 1 bis 5 Halogenatomen steht.R 8 preferably represents (C r C 4 ) alkyl or (C r C 4 ) haloalkyl having 1 to 5 halogen atoms.
R9 vorzugsweise für (C C4)-Alkyl steht.R 9 preferably represents (CC 4 ) alkyl.
steht bevorzugt für Wasserstoff, Amino, Chlor, Brom, Jod oder für eine der folgenden Gruppierungen:preferably represents hydrogen, amino, chlorine, bromine, iodine or one of the following groups:
-NH-CO-R10, -NHR1 1, -OR12, -SR12 oder -NR13-CX-C(Rl4, Rl5, Rl6)5 -NH-CO-R 10 , -NHR 1 1 , -OR 12 , -SR 12 or -NR 13 -CX-C (Rl 4 , Rl5, Rl6) 5
wobeiin which
RIO bevorzugt für (C1-C4)-Alkyl, (CrC4)-Halogenalkyl mit 1 bis 5 Halo- genatomen, (C]-C4)-Alkoxy-(C]-C4)-alkyl oder für jeweils gegebenenfalls einfach bis fünffach, gleich oder verschieden substituiertes Phenyl, Phenoxy oder Pyridyl steht, wobei als Substituenten die oben für R2 bereits genannten Phenylsubstituenten infrage kommen, R1 1 bevorzugt für (CrC4)-Alkyl, (C2-C4)-Alkenyl, (C2-C4)- Alkinyl,- Formyl, (CrC4)-Alkyl-carbonyl, (Cι-C4)-Halogenalkyl-carbonyl mit 1 bis 5 Halogenatomen oder (Cι-C4)-Alkoxy-carbonyl steht,RIO is preferred for (C 1 -C 4 ) alkyl, (C r C 4 ) haloalkyl with 1 to 5 halogen atoms, (C] -C 4 ) alkoxy- (C ] -C 4 ) alkyl or for each is optionally monosubstituted to pentasubstituted, identically or differently, phenyl, phenoxy or pyridyl, the phenyl substituents already mentioned above for R 2 being suitable as substituents, R 1 1 preferably for (C r C 4 ) alkyl, (C 2 -C 4 ) alkenyl, (C 2 -C 4 ) alkynyl, - formyl, (C r C 4 ) alkyl carbonyl, (Cι -C 4 ) haloalkyl carbonyl having 1 to 5 halogen atoms or (-C-C 4 ) alkoxy carbonyl,
R12 bevorzugt für (C,-C4)- Alkyl, (C2-C4)- Alkenyl, (C2-C4)-Alkinyl, Di- (Cι-C )-alkylamino-(CrC4)-alkyl; gegebenenfalls einfach bis fünffach, gleich oder verschieden substituiertes Pheny l-(C]-C2)-alkyl steht, wobei als Substituenten die oben für R2 bereits genannten Phe- nylsubstituenten infrage kommen;R 12 preferably for (C, -C 4 ) alkyl, (C 2 -C 4 ) alkenyl, (C 2 -C 4 ) alkynyl, di- (-C-C) alkylamino- (C r C 4 ) -alkyl; optionally mono- to pentasubstituted, identically or differently substituted, phenyl (C ) -C 2 -alkyl, where the phenyl substituents already mentioned above for R 2 are suitable as substituents;
oder für die Gruppierung -P(=Y)(OR17)(SR18) steht,or stands for the grouping -P (= Y) (OR 17 ) (SR 18 ),
wobeiin which
R17 und R18 unabhängig voneinander bevorzugt für (CrC4)-Alkyl stehen undR 17 and R 18 independently of one another preferably represent (C r C 4 ) -alkyl and
Y für Sauerstoff oder Schwefel steht,Y represents oxygen or sulfur,
R13 bevorzugt für Wasserstoff, (CrC4)- Alkyl, (C,-C4)-Alkoxy-(C,-C4)- alkyl, Propargyl, Allyl, (CrC4)-Alkoxy-carbonyl, (C,-C4)-Alkyl- carbonyl, für gegebenenfalls einfach bis fünffach, gleich oder verschieden substituiertes Benzyl steht, wobei als Substituenten die oben für R2 bereits genannten Phenylsubstituenten infrage kommen,R 13 preferably represents hydrogen, (C r C 4 ) -alkyl, (C, -C 4 ) -alkoxy- (C, -C 4 ) -alkyl, propargyl, allyl, (C r C 4 ) -alkoxy-carbonyl, (C 1 -C 4 ) -alkylcarbonyl, stands for benzyl which is optionally monosubstituted to pentasubstituted by identical or different substituents, the phenyl substituents already mentioned above for R 2 being suitable as substituents,
oder für die Gruppierung -CO-C(R14, R15, R16) steht,or represents the grouping -CO-C (R 14 , R 15 , R 16 ),
R ' 4 bevorzugt für Wasserstoff, (C , -C4)- Alkyl, Halogen, (C , -C4)-Halogen- alkyl mit 1 bis 5 Halogenatomen oder für gegebenenfalls einfach bis fünffach, gleich oder verschieden substituiertes Phenyl steht, wobei als Substituenten die oben für R2 bereits genannten Phenylsubstituenten infrage kommen,R ' 4 preferably represents hydrogen, (C, -C 4 ) alkyl, halogen, (C, -C 4 ) haloalkyl having 1 to 5 halogen atoms or optionally optionally up to five times, identical or differently substituted phenyl, where as Substituents which are suitable for phenyl substituents already mentioned above for R 2 ,
R15 bevorzugt für Wasserstoff, (Cj-C )-Alkyl, Halogen, (Cι-C4)-Halogen- alkyl und (Cι-C )-Halogenalkoxy-(C]-C )-alkyl mit jeweils 1 bis 5R 15 is preferably hydrogen, (Cj-C) -alkyl, halogen, (-C-C 4 ) -haloalkyl and (Cι-C) -haloalkoxy- (C ] -C) alkyl, each with 1 to 5
Halogenatomen, (C x -C4)-Alkylthio-(C , -C4)-alkyl, (C , -C4)- Alky lsul- fιnyl-(CrC4)-alkyl, (CrC4)- Alkylsulfonyl -(CrC4)-alkyl, (CrC4)- Alkoxy-[(C]-C4)-alkoxy]r-(C]-C4)-alkyl mit r = 0 bis 2, Hydroxy, (Cj-C4)-Alkoxy-carbonyl-(CrC4)-alkyl und (CrC4)- Alkoxy steht, oderHalogen atoms, (C x -C 4 ) -alkylthio- (C, -C 4 ) -alkyl, (C, -C 4 ) - alkylsul-fιnyl- (C r C 4 ) -alkyl, (C r C 4 ) Alkylsulfonyl - (C r C 4 ) -alkyl, (C r C 4 ) -alkoxy - [(C ] -C 4 ) -alkoxy] r - (C ] -C 4 ) -alkyl with r = 0 to 2, Hydroxy, (C j -C 4 ) alkoxy-carbonyl- (C r C 4 ) alkyl and (C r C 4 ) alkoxy, or
R14 und R15 gemeinsam mit dem Kohlenstoffatom, an das sie gebunden sind, bevorzugt für ein 5- bis 6- oder 7-gliedriges Ringsystem stehen, das gegebenenfalls bis zu zwei gleiche oder verschiedene Hetero- atome, wie O-, S- oder N- Atome, enthalten kann,R 14 and R 15 together with the carbon atom to which they are attached preferably represent a 5- to 6- or 7-membered ring system which may optionally have up to two identical or different hetero atoms, such as O, S or Can contain N atoms,
R16 bevorzugt für Hydroxy, (Cj-C4)-Alkoxy, (CrC4)-Halogenalkoxy mit 1 bis 5 Halogenatomen oder (C]-C4)-Alkoxy-[(C]-C4)-alkoxy]q mit q = 1 oder 2 steht,R 16 is preferably for hydroxy, (Cj-C 4 ) -alkoxy, (C r C 4 ) -haloalkoxy with 1 to 5 halogen atoms or (C] -C 4 ) -alkoxy - [(C ] -C 4 ) -alkoxy] q stands with q = 1 or 2,
X bevorzugt für Sauerstoff oder Schwefel steht.X preferably represents oxygen or sulfur.
Ar steht bevorzugt für jeweils gegebenenfalls einfach bis dreifach, gleich oder verschieden substituiertes Phenyl oder Pyridyl, wobei als Substituenten jeweils die oben für R2 bereits genannten Phenylsubstituenten infrage kommen.Ar preferably represents phenyl or pyridyl which is in each case monosubstituted to trisubstituted by identical or different substituents, the phenyl substituents already mentioned above for R 2 being suitable as substituents.
R2 steht besonders bevorzugt für (C C4)- Alkyl, (C2-C4)- Alkenyl, (C2-C4)-R 2 particularly preferably represents (CC 4 ) - alkyl, (C 2 -C 4 ) - alkenyl, (C 2 -C 4 ) -
Alkinyl. Cyan-(C,-C2)-alkyl. Thiocyanato-(CrC2)-alkyl, Nitro-(C,-C2)- alkyl, (C,-C4)-Alkylthio-(CrC2)-alkyl, (C,-C4)-Alkylsulfιnyl-(CrC2)-alkyl,Alkynyl. Cyan- (C, -C 2 ) alkyl. Thiocyanato- (C r C 2 ) -alkyl, nitro- (C, -C 2 ) -alkyl, (C, -C 4 ) -alkylthio- (C r C 2 ) -alkyl, (C, -C 4 ) - Alkylsulfionyl (C r C 2 ) alkyl,
(C , -C4)- Alky lsulfonyl-(C , -C2)-alky 1, (C , -C2)-Halogenalky lthio-(C , -C2)- alkyl mit 1 bis 5 gleichen oder verschiedenen Halogenatomen aus der Reih Fluor, Chlor und Brom, (CrC2)-Halogenalky lsulfmy l-(CrC2)-alkyl und (C,- C2)-Halogenalkylsulfonyl-(Cj-C )-alkyl mit jeweils 1 bis 5 gleichen oder verschiedenen Halogenatomen aus der Reihe Fluor, Chlor und Brom, (C2- C4)-Alkenylthio-(CrC2)-alkyl, (C2-C4)-Alkinylthio-(CrC2)-alkyl, (CrC2)-(C, -C 4 ) - alkylsulfonyl- (C, -C 2 ) -alkyl 1, (C, -C 2 ) -haloalkyl-thio- (C, -C 2 ) - alkyl with 1 to 5 identical or different halogen atoms from the series fluorine, chlorine and bromine, (C r C 2 ) -haloalky lsulfmy l- (C r C 2 ) -alkyl and (C, - C 2 ) -haloalkylsulfonyl- (Cj -C) -alkyl each having 1 to 5 identical or different halogen atoms from the series fluorine, chlorine and bromine, (C 2 - C 4 ) -alkenylthio- (C r C 2 ) -alkyl, (C 2 -C 4 ) - Alkynylthio- (C r C 2 ) alkyl, (C r C 2 ) -
Alkoxy-carbonyl-(C i -C )-alkyl, (C 1 -C2)-Halogenalkoxy-carbonyl-(C j -C2)- alkyl mit 1 bis 5 gleichen oder verschiedenen Halogenatomen aus der Reihe Fluor, Chlor und Brom, (Cι-C4)-Alkoxy-carbonyl, (CrC )-Alkyl-carbonyl, (C ! -C4)- Alkoxy-(C j -C2)-alkyl, (C , -C2)- Alkoxy-(C , -C2)-alkylthio-(C , -C2)- alkyl, (C1-C2)-Halogenalkoxy-(C1-C2)-alkylthio-(C1-C2)-alkyl mit 1 bis 5 gleichen oder verschiedenen Halogenatomen aus der Reihe Fluor, Chlor und Brom, (C , -C2)-Alkylamino-(C , -C2)-alkyl, Di-(C , -C2)-alkylamino-(C , -C2)- alkyl; für jeweils gegebenenfalls einfach bis dreifach, gleich oder verschieden sub- stituiertes Cyclopropyl, Cyclopentyl und Cyclohexyl, wobei als Substituenten genannt seien:Alkoxy-carbonyl- (C i -C) alkyl, (C 1 -C 2 ) -haloalkoxy-carbonyl- (C j -C 2 ) alkyl with 1 to 5 identical or different halogen atoms from the series fluorine, chlorine and bromine , (-C-C 4 ) -alkoxy-carbonyl, (C r C) -alkyl-carbonyl, (C! -C 4 ) - alkoxy- (C j -C 2 ) -alkyl, (C, -C 2 ) - Alkoxy- (C, -C 2 ) -alkylthio- (C, -C 2 ) -alkyl, (C 1 -C 2 ) -haloalkoxy- (C 1 -C 2 ) -alkylthio- (C 1 -C 2 ) - alkyl with 1 to 5 identical or different halogen atoms from the series fluorine, chlorine and bromine, (C, -C 2 ) alkylamino- (C, -C 2 ) alkyl, di- (C, -C 2 ) alkylamino- (C, -C 2 ) alkyl; for cyclopropyl, cyclopentyl and cyclohexyl which are optionally monosubstituted to trisubstituted in the same or different ways, the following being mentioned as substituents:
Methyl, Ethyl, Methoxy, Ethoxy, Fluor, Chlor, Brom, Trifluormethyl und Trifluormethoxy; sowie für jeweils gegebenenfalls einfach bis dreifach, gleich oder verschieden substituiertes Phenyl, Benzyl, Phenoxymethyl, Phenoxyethyl, Phenylthiome- thyl, Phenylthioethyl, Benzyloxymethyl, Benzylthiomethyl, Pyridyl oder Pyridylmethyl, wobei als Phenyl- bzw. Pyridylsubstituenten genannt seien: Fluor, Chlor, Brom, (C,-C4)-Alkyl, Allyl, (CrC4)- Alkoxy, Allyloxy, (C,- C2)-Alkylthio; (CrC2)-Halogenalkyl oder (CrC2)-Halogenalkoxy oder (Cr C2)-Halogenalkylthio mit jeweils 1 bis 5 gleichen oder verschiedenen Halogenatomen aus der Reihe Fluor, Chlor und Brom; Cyano, Nitro, Hydroxy, Hydrazino, Dimethylhydrazino, Amino, Methylamino, Dimethylamino, Imi- nomethyl, (C|-C2)-Alkyl-carbonyl, (C]-C2)-Alkyl-carbonyloxy; jeweils gegebenenfalls einfach bis zweifach, gleich oder verschieden durch Fluor, Chlor, Brom, Methyl, Ethyl, Methoxy, Trifluormethyl, Trifluormethoxy oder Trifluormethylthio substituiertes Phenyl oder Phenoxy; SF5 oder die Gruppie-Methyl, ethyl, methoxy, ethoxy, fluorine, chlorine, bromine, trifluoromethyl and trifluoromethoxy; as well as for phenyl, benzyl, phenoxymethyl, phenoxyethyl, phenylthiomethyl, phenylthioethyl, benzyloxymethyl, benzylthiomethyl, pyridyl or pyridylmethyl, which are optionally monosubstituted to trisubstituted in the same or different ways, the following being mentioned as phenyl or pyridyl substituents: fluorine, chlorine, bromine, (C, -C 4 ) alkyl, allyl, (C r C 4 ) alkoxy, allyloxy, (C, -C 2 ) alkylthio; (C r C 2 ) haloalkyl or (C r C 2 ) haloalkoxy or (C r C 2 ) haloalkylthio each having 1 to 5 identical or different halogen atoms from the series fluorine, chlorine and bromine; Cyano, nitro, hydroxy, hydrazino, dimethylhydrazino, amino, methylamino, dimethylamino, imino nomethyl, (C | -C 2) alkyl-carbonyl, (C] -C2) alkyl-carbonyloxy; each optionally single to double, identical or different by fluorine, chlorine, bromine, methyl, ethyl, methoxy, trifluoromethyl, trifluoromethoxy or Trifluoromethylthio substituted phenyl or phenoxy; SF 5 or the group
wobeiin which
R' und R" unabhängig voneinander für Wasserstoff oder (CrC4)- Alkyl stehen undR 'and R "independently of one another represent hydrogen or (C r C 4 ) alkyl and
Z für -CO oder -S02 steht.Z represents -CO or -S0 2 .
R2 steht für m = 0 zusätzlich besonders bevorzugt für SCN, Chlor, Jod, Nitro, Cyano, Hydroxy, Chlorsulfonyl, (CrC2)-Alkoxy, Allyloxy, (CrC2)-Halo- genalkyl oder (Cj-C2)-Halogenalkoxy mit jeweils 1 bis 5 gleichen oder verschiedenen Halogenatomen aus der Reihe Fluor, Chlor und Brom; (Cj-C2)- Alkyl-carbonyloxy, Formyl, -C≡C-Si(CH3)3; für gegebenenfalls einfach bis zweifach, gleich oder verschieden substituiertes Phenoxy, wobei als Substituenten die oben für R2 bereits genannten Substituenten infrage kommen; ferner für -CONH2, -CSNH2, -CON(CH3)2, -CON(C2H5)2, -CH=NOCH3, -CH=NOC2H5, -CH(CH3)=NOCH3 und -CH(OH)CF3.R 2 stands for m = 0 additionally particularly preferably for SCN, chlorine, iodine, nitro, cyano, hydroxyl, chlorosulfonyl, (C r C 2 ) alkoxy, allyloxy, (C r C 2 ) haloalkyl or (C j -C 2 ) haloalkoxy, each having 1 to 5 identical or different halogen atoms from the series fluorine, chlorine and bromine; (C j -C 2 ) - alkyl-carbonyloxy, formyl, -C≡C-Si (CH 3 ) 3 ; for phenoxy which is monosubstituted or disubstituted in the same way or differently, the substituents which may be mentioned are those already mentioned for R 2 ; further for -CONH 2 , -CSNH 2 , -CON (CH 3 ) 2 , -CON (C 2 H 5 ) 2 , -CH = NOCH 3 , -CH = NOC 2 H 5 , -CH (CH 3 ) = NOCH 3 and -CH (OH) CF 3 .
R3 steht besonders bevorzugt für Wasserstoff, Amino, Chlor, (CrC4)-Alkyl- amino sowie für die Gruppierung -NH-CO-R10 R 3 particularly preferably represents hydrogen, amino, chlorine, (C r C 4 ) -alkylamino and the group -NH-CO-R 10
wobeiin which
R10 besonders bevorzugt für (CrC4)- Alkyl, (CrC )-Halogenalkyl mit 1 bis 5 gleichen oder verschiedenen Halogenatomen aus der Reihe Fluor, Chlor und Brom sowie für jeweils gegebenenfalls einfach bis zweifach, gleich oder verschieden substituiertes Phenyl und Phenoxy steht, wobei als Substituenten die oben für R2 bereits genannten Phenylsubstituenten infrage kommen.R 10 is particularly preferably for (C r C 4 ) alkyl, (C r C) haloalkyl having 1 to 5 identical or different halogen atoms from the series fluorine, chlorine and bromine and for phenyl which is monosubstituted to disubstituted by identical or different substituents and phenoxy stands, with the phenyl substituents already mentioned above for R 2 being suitable as substituents.
Ar steht besonders bevorzugt für jeweils gegebenenfalls einfach bis dreifach, gleich oder verschieden durch Fluor, Chlor, Brom; (CrC2)-Halogenalkyl undAr particularly preferably represents in each case optionally one to three times, identical or different by fluorine, chlorine, bromine; (C r C 2 ) haloalkyl and
(CrC2)-Halogenalkoxy und (CrC2)-Halogenalkylthio und (CrC2)-Halogen- alkylsulfinyl und (Cι-C2)-Halogenalkylsulfonyl mit jeweils 1 bis 5 gleichen oder verschiedenen Halogenatomen aus der Reihe Fluor, Chlor und Brom; (CrC2)- Alkyl, (CrC2)- Alkoxy, Hydrazino, Dimethylhydrazino, Amino, Methylamino, Dimethylamino, Cyano, SF5 oder die Gruppierung(C r C 2 ) haloalkoxy and (C r C 2 ) haloalkylthio and (C r C 2 ) haloalkylsulfinyl and (C 1 -C 2 ) haloalkylsulfonyl each having 1 to 5 identical or different halogen atoms from the fluorine series , Chlorine and bromine; (C r C 2 ) alkyl, (C r C 2 ) alkoxy, hydrazino, dimethylhydrazino, amino, methylamino, dimethylamino, cyano, SF 5 or the grouping
wobeiin which
R' und R" unabhängig voneinander für Wasserstoff oder (C i -C )-Alkyl stehen undR 'and R "independently of one another represent hydrogen or (C i -C) alkyl and
Z für CO oder SO2 steht,Z represents CO or SO 2 ,
substituiertes Phenyl oder Pyridyl.substituted phenyl or pyridyl.
R2 steht ganz besonders bevorzugt für CH3, C2H5, -CH2-CH=CH2, -C≡CH, -CH2-C≡CH, -CH2-CN, -CH2-SCN, -CH2-N02, -CH2-S-CH3, -CH2-S-C2H5, -CH2CH2-S-CH3, -CH2CH2-S-C2H5, -CH2-SO-C2H5, -CH2-S02-C2H5, - CH2-S-CF3, CH2-SO-CF3, CH2-S02-CF3, -CH2-S-CH2-CH=CH2, -CH2-S-R 2 very particularly preferably represents CH 3 , C 2 H 5 , -CH 2 -CH = CH 2 , -C≡CH, -CH 2 -C≡CH, -CH 2 -CN, -CH 2 -SCN, - CH 2 -N0 2 , -CH 2 -S-CH 3 , -CH 2 -SC 2 H 5 , -CH 2 CH 2 -S-CH 3 , -CH 2 CH 2 -SC 2 H 5 , -CH 2 - SO-C 2 H 5, -CH 2 -S0 2 -C 2 H 5, - CH 2 -S-CF 3, CH 2 -SO-CF 3, CH 2 -S0 2 -CF 3, -CH 2 -S -CH 2 -CH = CH 2 , -CH 2 -S-
CH2-C≡CH, -CH2-CO-OCH3, -CH2-CO-OC2H5, -(CH2)2-CO-OCH3, -(CH2)2-CO-OC2H5, -CH2-CO-OCF3, -CO-OCH3, -CO-OC2H5, -CO-CH3, - CO-C2H5, -CH2-OCH3, -CH2-OC2H5, -CH2-S-CH2CH2-0-C2H5, -CH2-S- CH2CH2-0-CH2CF3, -CH2-NHC2H5, -CH2CH2-N(CH3)2, -CH2CH2- N(C2H5)2, Cyclopropyl, sowie für jeweils gegebenenfalls einfach bis dreifach, gleich oder verschieden substituiertes Benzyl. Benzyloxymethyl, Ben- zylthiomethyl, Phenoxymethyl, Phenoxyethyl, Phenylthiomethyl oder Phe- nylthioethyl, wobei jeweils als Phenylsubstituenten genannt seien: Fluor, Chlor, Trifluormethyl, Trifluormethoxy, Trifluormethylthio, Methoxy,CH 2 -C≡CH, -CH 2 -CO-OCH 3 , -CH 2 -CO-OC 2 H 5 , - (CH 2 ) 2 -CO-OCH 3 , - (CH 2 ) 2 -CO-OC 2 H 5 , -CH 2 -CO-OCF 3 , -CO-OCH 3 , -CO-OC 2 H 5 , -CO-CH 3 , - CO-C 2 H 5 , -CH 2 -OCH 3 , -CH 2 -OC 2 H 5 , -CH 2 -S-CH 2 CH 2 -0-C 2 H 5 , -CH 2 -S- CH 2 CH 2 -0-CH 2 CF 3 , -CH 2 -NHC 2 H 5 , -CH 2 CH 2 -N (CH 3 ) 2 , -CH 2 CH 2 - N (C 2 H 5 ) 2 , cyclopropyl, and for benzyl which is optionally monosubstituted to trisubstituted by identical or different substituents. Benzyloxymethyl, benzylthiomethyl, phenoxymethyl, phenoxyethyl, phenylthiomethyl or phenylthioethyl, phenyl substituents in each case being: fluorine, chlorine, trifluoromethyl, trifluoromethoxy, trifluoromethylthio, methoxy,
Hydrazino, Dimethylhydrazino, Amino, Methylamino, Dimethylamino, Cyano, Methylthio, -CONH2, -CSNH2, Phenyl, Chlorphenyl, Fluorphenyl, Dichlorphenyl, Phenoxy, Chlorphenoxy, Fluorphenoxy und Dichlorphenoxy.Hydrazino, dimethylhydrazino, amino, methylamino, dimethylamino, cyano, methylthio, -CONH 2 , -CSNH 2 , phenyl, chlorophenyl, fluorophenyl, dichlorophenyl, phenoxy, chlorophenoxy, fluorophenoxy and dichlorophenoxy.
R2 steht für m = 0 zusätzlich ganz besonders bevorzugt für SCN, Chlor, Jod,R 2 stands for m = 0 additionally very particularly preferably for SCN, chlorine, iodine,
Nitro, Cyano,Nitro, cyano,
-OCH3, -CF3, -OCF3, -0-COCH3, -OHT CI ■ -O-T' F. -CSNH2, -CON(CH3) , -CH=NOCH3 und -CH(OH)CF3.-OCH3, -CF3, -OCF3, -0-COCH3, -OHT CI ■ -OT 'F. -CSNH2, -CON (CH 3 ), -CH = NOCH 3 and -CH (OH) CF 3 .
R3 steht ganz besonders bevorzugt für Wasserstoff. Amino, Chlor, -NHCH-R 3 very particularly preferably represents hydrogen. Amino, chlorine, -NHCH-
-NHC2H5, -NH-CO-CF3, F, -NHC2H5, -NH-CO-CF3, F,
Ar steht ganz besonders bevorzugt für jeweils zweifach oder dreifach, gleich oder verschieden durch F, Cl, Br, CF3, OCF3, SCF3, SOCF3, SO2CF3, OCH2CF3, CH3 oder SF5 substituiertes Phenyl oder 2-Pyridyl.Ar very particularly preferably represents phenyl which is substituted twice or three times, identically or differently by F, Cl, Br, CF 3 , OCF 3 , SCF 3 , SOCF 3 , SO 2 CF 3 , OCH 2 CF 3 , CH 3 or SF 5 or 2-pyridyl.
Die oben aufgeführten oder in Vorzugsbereichen aufgeführten Restedefinitionen bzw. Erläuterungen gelten für die Endprodukte und für die Ausgangs- und Zwischenprodukte entsprechend. Diese Restedefinitionen können untereinander, also auch zwischen den jeweiligen Vorzugsbereichen, beliebig kombiniert werden. Erfindungsgemäß bevorzugt werden die Verbindungen der Formel (I), in welchen eine Kombination der vorstehend als bevorzugt (vorzugsweise) aufgeführten Bedeutungen vorliegt.The radical definitions or explanations listed above or listed in preferred areas apply accordingly to the end products and to the starting and intermediate products. These residual definitions can be combined with one another, i.e. also between the respective preferred areas. According to the invention, preference is given to the compounds of the formula (I) in which there is a combination of the meanings listed above as preferred (preferred).
Erfindungsgemäß besonders bevorzugt werden die Verbindungen der Formel (I), in welchen eine Kombination der vorstehend als besonders bevorzugt aufgeführten Bedeutungen vorliegt.According to the invention, particular preference is given to the compounds of the formula (I) in which there is a combination of the meanings listed above as being particularly preferred.
Erfindungsgemäß ganz besonders bevorzugt werden die Verbindungen der Formel (I), in welchen eine Kombination der vorstehend als ganz besonders bevorzugt aufgeführten Bedeutungen vorliegt.According to the invention, very particular preference is given to the compounds of the formula (I) in which there is a combination of the meanings listed above as being particularly preferred.
In den oben und nachstehend aufgeführten Restedefinitionen sind Kohlenwasserstoffreste, wie Alkyl oder Alkenyl - auch in Verbindungen mit Heteroatomen wie Alkoxy oder Alylthio - soweit möglich jeweils geradkettig oder verzweigt.In the radical definitions given above and below, hydrocarbon radicals, such as alkyl or alkenyl - also in compounds with heteroatoms such as alkoxy or allythio - are in each case straight-chain or branched as far as possible.
Bevorzugt sind Verbindungen der Formeln (IA-1) bis (IA-5)Compounds of the formulas (IA-1) to (IA-5) are preferred
in welchenin which
Ar, R2, R3, m und n für die oben genannten allgemeinen, vorzugsweisen, besonders bevorzugten und ganz besonders bevorzugten Bedeutungen stehen.Ar, R 2 , R 3 , m and n stand for the abovementioned general, preferred, particularly preferred and very particularly preferred meanings.
Beispiele für die neuen substituerten 3-Thiocarbamoylpyrazole sind in den Tabellen 1 bis 14 aufgeführt: Tabelle 1Examples of the new substituted 3-thiocarbamoylpyrazoles are listed in Tables 1 to 14: Table 1
Verbindungen der Tabelle 1 entsprechen der allgemeinen Formel (IB), in welcher fürCompounds in Table 1 correspond to the general formula (IB), in which for
folgende Substituentenkombinationen gelten: the following combinations of substituents apply:
R2 R3 R 2 R 3
CH3 0 NH2 CH 3 0 NH 2
CH3 1 NH2 CH 3 1 NH 2
CH3 1 NHC2H5 CH 3 1 NHC 2 H 5
C2H5 2 NH2 C 2 H 5 2 NH 2
C2H5 2 NHC2H5 C 2 H 5 2 NHC 2 H 5
C2H5 1 NH-COCF3 C 2 H 5 1 NH-COCF 3
C2H5 1 H-CO-OHQ CIC 2 H 5 1 H-CO-OHQ CI
CH2-SCF3 1 NH2 CH 2 -SCF 3 1 NH 2
-<l 1 NH9 - <l 1 NH 9
-CH2-CN 1 NH2 -CH 2 -CN 1 NH 2
-CH2-NO2 0 NH2 -CH 2 -NO 2 0 NH 2
-CH2-S-CF3 0 H-CH 2 -S-CF 3 0 H
-CH2-S-CF3 0 Cl-CH 2 -S-CF 3 0 Cl
-CH -S-C H5 1 NH2 -CH -SC H 5 1 NH 2
-CO-O-C2H5 0 H-CO-OC 2 H 5 0 H
-CH2-0-C2H5 1 NH2 -CH 2 -0-C 2 H 5 1 NH 2
-CH2CH2-N(C2H5)2 2 NH2 -CH 2 CH 2 -N (C 2 H 5 ) 2 2 NH 2
-CH2-C≡CH 1 NH2 -CH 2 -C≡CH 1 NH 2
-CH2-CH=CH2- 1 NH2 -CH 2 -CH = CH 2 - 1 NH 2
-CH2-SO-CF3 1 NH2 -CH 2 -SO-CF 3 1 NH 2
-CH2-S-CH2-CH=CH2 1 NH2 -CH 2 -S-CH 2 -CH = CH 2 1 NH 2
-CH2-S-CH2-C≡CH 1 NH2 -CH 2 -S-CH 2 -C≡CH 1 NH 2
-CH2-CO-OCF3 1 NH2 -CH 2 -CO-OCF 3 1 NH 2
CH2-S-CH2CH2-O-CH2CF3 1 NH2 CH 2 -S-CH 2 CH 2 -O-CH 2 CF 3 1 NH 2
-CH2CH2-S-CH3 0 NHCH3 -CH 2 CH 2 -S-CH 3 0 NHCH 3
-CH2-SCN 0 NH2 -CH 2 -SCN 0 NH 2
-CH2-SO2-C2H5 2 NH2 -CH 2 -SO 2 -C 2 H 5 2 NH 2
-CO-OCH3 1 NH2 -CO-OCH 3 1 NH 2
-CH2CH2-S-C2H5 0 NHo Tabelle 2-CH 2 CH 2 -SC 2 H 5 0 NHo Table 2
Tabelle 2 enthält Verbindungen der allgemeinen Formel (IB), in welcherTable 2 contains compounds of the general formula (IB), in which
und für R2, n und R3 die Substituentenkombinationen, wie in Tabelle 1 aufgelistet, gelten. and for R 2 , n and R 3 the substituent combinations as listed in Table 1 apply.
Tabelle 3Table 3
Tabelle 3 enthält Verbindungen der allgemeinen Formel (IB), in welcherTable 3 contains compounds of the general formula (IB), in which
und für R2, n und R3 die Substituentenkombinationen, wie in Tabelle 1 aufgelistet, gelten. and for R 2 , n and R 3 the substituent combinations as listed in Table 1 apply.
Tabelle 4Table 4
Tabelle 4 enthält Verbindungen der allgemeinen Formel (IB), in welcherTable 4 contains compounds of the general formula (IB), in which
und für R2, n und R3 die Substituentenkombinationen, wie in Tabelle 1 aufgelistet, gelten. and for R 2 , n and R 3 the substituent combinations as listed in Table 1 apply.
Tabelle 5Table 5
Tabelle 5 enthält Verbindungen der allgemeinen Formel (IB), in welcher und für R2, n und R3 die Substituentenkombinationen, wie in Tabelle 1 aufgelistet, gelten.Table 5 contains compounds of the general formula (IB), in which and for R 2 , n and R 3 the substituent combinations as listed in Table 1 apply.
Tabelle 6Table 6
Tabelle 6 enthält Verbindungen der allgemeinen Formel (IB), in welcherTable 6 contains compounds of the general formula (IB), in which
und für R2, n und R3 die Substituentenkombinationen, wie in Tabelle 1 aufgelistet, gelten. and for R 2 , n and R 3 the substituent combinations as listed in Table 1 apply.
Tabelle 7Table 7
Tabelle 7 enthält Verbindungen der allgemeinen Formel (IB), in welcherTable 7 contains compounds of the general formula (IB), in which
und für R2, n und R3 die Substituentenkombinationen, wie in Tabelle 1 aufgelistet, gelten. and for R 2 , n and R 3 the substituent combinations as listed in Table 1 apply.
Tabelle 8Table 8
Tabelle 8 enthält Verbindungen der allgemeinen Formel (IB), in welcherTable 8 contains compounds of the general formula (IB), in which
und für R2, n und R3 die Substituentenkombinationen, wie in Tabelle 1 aufgelistet, gelten. Tabelle 9 and for R 2 , n and R 3 the substituent combinations as listed in Table 1 apply. Table 9
Tabelle 9 enthält Verbindungen der allgemeinen Formel (IB), in welcherTable 9 contains compounds of the general formula (IB), in which
und für R2, n und R3 die Substituentenkombinationen, wie in Tabelle 1 aufgelistet, gelten. and for R 2 , n and R 3 the substituent combinations as listed in Table 1 apply.
Tabelle 10Table 10
Tabelle 10 enthält Verbindungen der allgemeinen Formel (IB), in welcher H,Table 10 contains compounds of the general formula (IB) in which H,
und für R2, n und R3 die Substituentenkombinationen, wie in Tabelle 1 aufgelistet, gelten.and for R 2 , n and R 3 the substituent combinations as listed in Table 1 apply.
Tabelle 11Table 11
Tabelle 11 enthält Verbindungen der allgemeinen Formel (IB), in welcherTable 11 contains compounds of the general formula (IB), in which
CkCk
Ar = -Λ SF5 Ar = -Λ SF 5
Cl^~^ und für R2, n und R3 die Substituentenkombinationen, wie in Tabelle 1 aufgelistet, gelten.Cl ^ ~ ^ and for R 2 , n and R 3 the substituent combinations, as listed in Table 1, apply.
Tabelle 12Table 12
Tabelle 12 enthält Verbindungen der allgemeinen Formel (IB), in welcher und für R2, n und R3 die Substituentenkombinationen, wie in Tabelle 1 aufgelistet, gelten.Table 12 contains compounds of the general formula (IB), in which and for R 2 , n and R 3 the substituent combinations as listed in Table 1 apply.
Tabelle 13Table 13
Verbindungen der Tabelle 13 entsprechen der allgemeinen Formel (IB), in welcher fürCompounds in Table 13 correspond to the general formula (IB), in which for
folgende Substituentenkombinationen gelten: the following combinations of substituents apply:
R2 R3 R 2 R 3
CH3 0 NH2 CH 3 0 NH 2
CH3 1 NH2 CH 3 1 NH 2
CH3 1 NHC2H5 CH 3 1 NHC 2 H 5
C2H5 2 NH2 C 2 H 5 2 NH 2
C2H5 2 NHC2H5 C 2 H 5 2 NHC 2 H 5
C2H5 1 NH-COCF3 C 2 H 5 1 NH-COCF 3
C2H5 1C2H5 1
NH-CO-O- -ClNH-CO-O- -Cl
-CH2-SCF3 1 NH2 -CH 2 -SCF 3 1 NH 2
NH? NH ?
-C^-S-CH -^-CI-C ^ -S-CH - ^ - CI
-CH2-CN 1 NH2 -CH 2 -CN 1 NH 2
-CH2-NO2 0 NH2 -CH 2 -NO 2 0 NH 2
-CH2-SCF3 0 H Tabelle 14-CH 2 -SCF 3 0 H Table 14
Verbindungen der Tabelle 14 entsprechen der allgemeinen Formel (IC), in welcher fürCompounds in Table 14 correspond to the general formula (IC), in which for
folgende Substituentenkombinationen gelten: the following combinations of substituents apply:
R2 R3 R 2 R 3
-C≡CH NH2 -C≡CH NH 2
CF3 NH2 CF 3 NH 2
J NH2 J NH 2
-CH=NOCH3 NH2 -CH = STILL 3 NH 2
-OCF3 NH2 -OCF 3 NH 2
-C≡C-Si(CH3)3 NH2 -C≡C-Si (CH 3 ) 3 NH 2
-C≡CH NH-COCH3 -C≡CH NH-COCH 3
-C≡CH NH-C2H5 -C≡CH NH-C 2 H 5
-SCN NH2 -SCN NH 2
-C≡CH NH-CO-CF3 -C≡CH NH-CO-CF 3
-NO2 NH2 -NO 2 NH 2
-NO2 Cl -C≡CH Cl-NO 2 Cl -C≡CH Cl
-C≡CH H-C≡CH H
-CH3 NH2 -CH 3 NH 2
C2H5 NH2 C 2 H 5 NH 2
-OCH3 NH2 -OCH 3 NH 2
-CO-N(CH3)2 NH2 -CO-N (CH 3 ) 2 NH 2
-CH(OH)CF3 NH2 -CH (OH) CF 3 NH 2
-CS-NH2 NH2 -CS-NH 2 NH 2
-O-COCH3 NH2 -O-COCH 3 NH 2
-SO2Cl NH2 -SO 2 Cl NH 2
Verwendet man beispielsweise 5-Amino-3-cyano-4-(ethylthio)-l-(2,6-dichlor-4-tri- fluormethylphenyl)-pyrazol und Schwefelwasserstoff als Ausgangsstoffe, so kann der Reaktionsablauf des erfindungsgemäßen Verfalirens (a) durch das folgende Formelschema wiedergegeben werden: If, for example, 5-amino-3-cyano-4- (ethylthio) -1- (2,6-dichloro-4-trifluoromethylphenyl) pyrazole and hydrogen sulfide are used as starting materials, the course of the reaction according to the invention (a) can be carried out the following formula scheme can be reproduced:
Verwendet man beispielsweise l-(2,6-Dichlor-4-trifluormethylphenyl)-3-thiocarb- amoyl-5-ethylamino-pyrazol und Ethylsulfensäurechlorid als Ausgangsstoffe, so kann der Reaktionsablauf des erfindungsgemäßen Verfahrens (b) durch das folgende Formelschema wiedergegeben werden:If, for example, 1- (2,6-dichloro-4-trifluoromethylphenyl) -3-thiocarbamoyl-5-ethylamino-pyrazole and ethylsulfenoyl chloride are used as starting materials, the reaction sequence of process (b) according to the invention can be represented by the following formula:
Verwendet man beispielsweise 5-Ethylamino-3-thiocarbamoyl-4-ethylthio-l-(2,6-di- chlor-4-trifluormethyl-phenyl)-pyrazol und Schwefelwasserstoff als Ausgangsstoffe, so kann der Reaktionsablauf des erfindungsgemäßen Verfahrens (c) durch das folgende Formelschema wiedergegeben werden: If, for example, 5-ethylamino-3-thiocarbamoyl-4-ethylthio-l- (2,6-di-chloro-4-trifluoromethyl-phenyl) pyrazole and hydrogen sulfide are used as starting materials, the course of the reaction of process (c) according to the invention can be carried out by the following formula scheme can be reproduced:
Die zur Durchführung des erfindungsgemäßen Verfahrens (a) als Ausgangsstoffe zu verwendenden 3-Cyanopyrazol-Derivate der Formel (II) sind bekannt (vgl. z.B. EP 0 295 117, GB 2 308 365, WO 98/04 530 und WO 97/07 102) und/oder können in Analogie zu bekannten Verfahren hergestellt werden.The 3-cyanopyrazole derivatives of the formula (II) to be used as starting materials for carrying out process (a) according to the invention are known (cf. for example EP 0 295 117, GB 2 308 365, WO 98/04 530 and WO 97/07 102 ) and / or can be produced in analogy to known processes.
Die zur Durchführung des erfindungsgemäßen Verfahrens (b) als Ausgangsstoffe zu verwendenden 3-Thiocarbamoylpyrazol-Derivate der Formel (III) sind neu und teilweise Gegenstand einer eigenen älteren Anmeldung (vgl. die deutsche Patentanmeldung 196 50 197 vom 04.12.1996).The 3-thiocarbamoylpyrazole derivatives of the formula (III) to be used as starting materials for carrying out process (b) according to the invention are new and in part are the subject of a separate earlier application (cf. German patent application 196 50 197 of December 4, 1996).
Die Verbindungen der Formel (III) können erhalten werden, indem man 2-Cyanopy- razole der Formel (V)The compounds of formula (III) can be obtained by using 2-cyanopyrazoles of formula (V)
NCNC
N 3-1N 3-1
N R (V),N R (V),
ArAr
in welcherin which
Ar und R3~ ! die oben angegebene Bedeutung haben, gemäß dem erfindungsgemäßen Verfahren (a) mit Schwefelwasserstoff, gegebenen- - falls in Gegenwart eines Reaktionshilfsmittels und gegebenenfalls in Gegenwart eines Verdünnungsmittels umsetzt.Ar and R 3 ~! have the meaning given above, according to process (a) according to the invention with hydrogen sulfide, if appropriate - in the presence of a reaction auxiliary and if appropriate in the presence of a diluent.
Die 3-Cyanopyrazole der Formel (V) sind bekannt (vgl. z.B. EP 659 745) bzw. können sie nach allgemein üblichen Verfahren erhalten werden.The 3-cyanopyrazoles of the formula (V) are known (cf. e.g. EP 659 745) or they can be obtained by generally customary processes.
Die außerdem für das erfindungsgemäße Verfahren (b) als Ausgangsstoffe zu verwendenden Sulfenylhalogenide der Formel (IV) sind allgemein bekannte Verbindun- gen der organischen Chemie, und/oder lassen sich nach bekannten Verfahren herstellen.The sulfenyl halides of the formula (IV) which are also to be used as starting materials for process (b) according to the invention are generally known compounds of organic chemistry and / or can be prepared by known processes.
Die für das erfindungsgemäße Verfahren (c) als Ausgangsstoffe zu verwendenden 3- Thiocarbamoylpyrazol-Derivate der Formel (Ia) sind erfindungsgemäße Verbindun- gen.The 3-thiocarbamoylpyrazole derivatives of the formula (Ia) to be used as starting materials for process (c) according to the invention are compounds according to the invention.
Das erfindungsgemäße Verfahren (a) wird vorzugsweise unter Verwendung eines Verdünnungsmittels durchgeführt. Als Verdünnungsmittel kommen praktisch alle inerten organischen Lösungsmittel in Frage. Hierzu gehören vorzugsweise alipha- tische und aromatische, gegebenenfalls halogenierte Kohlenwasserstoffe wie Pentan,Process (a) according to the invention is preferably carried out using a diluent. Practically all inert organic solvents can be used as diluents. These preferably include aliphatic and aromatic, optionally halogenated hydrocarbons such as pentane,
Hexan, Heptan, Cyclohexan, Petrolether, Benzin, Ligroin, Benzol, Toluol, Xylol, Methylenchlorid, Ethylenchlorid, Chloroform, Tetrachlorkohlenstoff, Chlorbenzol und o-Dichlorbenzol, Ether wie Diethyl- und Dibutylether, Glykoldimethylether und Diglykoldimethylether, Tetrahydrofuran und Dioxan, Ketone wie Aceton, Methyl- ethyl-, Methyl-isopropyl- oder Methyl-isobutyl-keton, Ester wie Essigsäuremethylester oder -ethylester, Nitrile wie z.B. Acetonitril oder Propionitril, Amide wie z.B. Dimethylformamid, Dimethylacetamid und N-Methylpyrrolidon sowie Dimethyl- sulfoxid, Tetramethylensulfon oder Hexamethylenphosphorsäuretriamid.Hexane, heptane, cyclohexane, petroleum ether, gasoline, ligroin, benzene, toluene, xylene, methylene chloride, ethylene chloride, chloroform, carbon tetrachloride, chlorobenzene and o-dichlorobenzene, ethers such as diethyl and dibutyl ether, glycol dimethyl ether and diglycol dimethyl ether and tetrahanethane, tetrahydrofuran , Methyl ethyl, methyl isopropyl or methyl isobutyl ketone, esters such as methyl acetate or ethyl acetate, nitriles such as Acetonitrile or propionitrile, amides such as e.g. Dimethylformamide, dimethylacetamide and N-methylpyrrolidone as well as dimethyl sulfoxide, tetramethylene sulfone or hexamethylene phosphoric acid triamide.
Als Reaktionshilfsmittel können bei dem erfindungsgemäßen Verfahren (a) alle üblicherweise für derartige Umsetzungen verwendbaren Basen eingesetzt werden. Vor- zugsweise infrage kommen basische Stickstoffverbindungen, wie Trimethylamin5 Triethylamin, Tripropylamin, Tributylamin, Diisobutylamin, Dicyclohexylamin, Ethyldiisopropylamin, Ethyldicyclohexylamin, N,N-Dimethylbenzylamin, N,N-Di- methyl-anilin, Pyridin, 2-Methyl-, 3-Methyl-, 4-Methyl-, 2,4-Dimethyl-, 2,6-Dime- thyl-, 2-Ethyl-, 4-Ethyl- und 5-Ethyl-2-methyl-pyridin, l,5-Diazabicyclo[4,3,0]-non-All bases which can usually be used for such reactions can be used as reaction auxiliaries in process (a) according to the invention. In front- Basic nitrogen compounds, such as trimethylamine 5 triethylamine, tripropylamine, tributylamine, diisobutylamine, dicyclohexylamine, ethyldiisopropylamine, ethyldicyclohexylamine, N, N-dimethylbenzylamine, N, N-dimethyl-aniline, pyridine, 2-methyl-, 3-methyl, are also suitable. , 4-methyl, 2,4-dimethyl, 2,6-dimethyl, 2-ethyl, 4-ethyl and 5-ethyl-2-methyl-pyridine, l, 5-diazabicyclo [4, 3.0] -non-
5-en (DBN), l,8-Diazabicyclo-[5,4,0]-undec-7-en (DBU) oder 1 ,4-Diazabicyclo- [2,2,2]-octan (DABCO). Es ist auch möglich, ein im Überschuß eingesetztes Reaktionshilfsmittel als Verdünnungsmittel zu verwenden.5-ene (DBN), 1,8-diazabicyclo- [5,4,0] -undec-7-ene (DBU) or 1,4-diazabicyclo- [2,2,2] octane (DABCO). It is also possible to use a reaction auxiliary used in excess as the diluent.
Die Reaktionstemperaturen können bei dem erfindungsgemäßen Verfahren (a) in einem größeren Bereich variiert werden. Im allgemeinen arbeitet man bei Temperaturen zwischen 0°C und 100°C, vorzugsweise bei Temperaturen zwischen 10°C und 80°C.The reaction temperatures can be varied within a substantial range in process (a) according to the invention. In general, temperatures between 0 ° C and 100 ° C, preferably at temperatures between 10 ° C and 80 ° C.
Das erfindungsgemäße Verfahren (a) wird im allgemeinen unter Normaldruck durchgeführt. Es ist jedoch auch möglich, unter erhöhtem oder vermindertem Druck zu arbeiten.Process (a) according to the invention is generally carried out under normal pressure. However, it is also possible to work under increased or reduced pressure.
Zur Durchführung des erfindungsgemäßen Verfahrens (a) wird der Schwefelwasser- Stoff in der Regel im Überschuß eingesetzt. Die Reaktionen werden im allgemeinen in einem geeigneten Verdünnungsmittel in Gegenwart einer basischen Stickstoffverbindung durchgeführt. Die Aufarbeitung erfolgt nach üblichen Methoden (vgl. die Herstellungsbeispiele) .To carry out process (a) according to the invention, the hydrogen sulfide is generally used in excess. The reactions are generally carried out in a suitable diluent in the presence of a basic nitrogen compound. Working up is carried out using customary methods (cf. the production examples).
Als Verdünnungsmittel zur Durchführung des erfindungsgemäßen Verfahrens (b) kommen inerte organische Lösungsmittel infrage. Hierzu gehören insbesondere ali- phatische, alicyclische oder aromatische, gegebenenfalls halogenierte Kohlenwasserstoffe, wie beispielsweise Benzin, Benzol, Toluol, Xylol, Chlorbenzol, Petrolether, Hexan, Cyclohexan, Dichlormethan, Chloroform, Tetrachlorkohlenstoff; Ether, wie Diethylether, Dioxan, Tetrahydrofuran oder Ethylenglykoldimethyl- oder -diethyl- ether, Ketone wie Aceton oder Butanon, Nitrile, wie Acetonitril oder Propionitril: Amide, wie Dimethylformamid, Dimethylacetamid, N-Methylformanilid, N-Methyl- pyrrolidon oder Hexamethylphosphorsäuretriamid, Ester, wie Essigsäureethylester, Sulfoxide, wie Dimethylsulfoxid oder Säuren, wie beispielsweise Essigsäure.Inert organic solvents are suitable as diluents for carrying out process (b) according to the invention. These include in particular aliphatic, alicyclic or aromatic, optionally halogenated hydrocarbons, such as, for example, gasoline, benzene, toluene, xylene, chlorobenzene, petroleum ether, hexane, cyclohexane, dichloromethane, chloroform, carbon tetrachloride; Ethers such as diethyl ether, dioxane, tetrahydrofuran or ethylene glycol dimethyl or diethyl ether, ketones such as acetone or butanone, nitriles such as acetonitrile or propionitrile: Amides such as dimethylformamide, dimethylacetamide, N-methylformanilide, N-methylpyrrolidone or hexamethylphosphoric acid triamide, esters such as ethyl acetate, sulfoxides such as dimethyl sulfoxide or acids such as acetic acid.
Das erfindungsgemäße Verfahren (b) kann gegebenenfalls in Gegenwart eines Reaktionshilfsmittels durchgeführt werden. Als solche kommen alle üblichen anorganischen oder organischen Basen infrage. Hierzu gehören beispielsweise Alkalimetall- hydroxide, wie Natriumhydroxid oder Kaliumhydroxid, Alkalimetallcarbonate oder Hydrogencarbonate, wie Natriumcarbonat, Kaliumcarbonat oder Natriumhydrogen- carbonat sowie tertiäre Amine, wie Triethylamin, N,N-Dimethylanilin, Pyridin, N,N-If appropriate, process (b) according to the invention can be carried out in the presence of a reaction auxiliary. All conventional inorganic or organic bases are suitable as such. These include, for example, alkali metal hydroxides, such as sodium hydroxide or potassium hydroxide, alkali metal carbonates or hydrogen carbonates, such as sodium carbonate, potassium carbonate or sodium hydrogen carbonate, and tertiary amines, such as triethylamine, N, N-dimethylaniline, pyridine, N, N-
Dimethylaminopyridin, Diazabicyclooctan (DABCO), Diazabicyclononen (DBN) oder Diazabicycloundecen (DBU).Dimethylaminopyridine, diazabicyclooctane (DABCO), diazabicyclonones (DBN) or diazabicycloundecene (DBU).
Die Reaktionstemperaturen können bei der Durchführung des erfindungsgemäßen Verfahrens (b) in einem größeren Bereich variiert werden. Im allgemeinen arbeitet man bei Temperaturen zwischen -20°C und +120°C, vorzugsweise bei Temperaturen zwischen 0°C und +50°C.The reaction temperatures can be varied within a substantial range when carrying out process (b) according to the invention. In general, temperatures between -20 ° C and + 120 ° C, preferably at temperatures between 0 ° C and + 50 ° C.
Zur Durchführung des erfindungsgemäßen Verfahrens (b) setzt man pro Mol in an 4- Stellung substituiertem 1 -Arylpyrazol der Formel (III) im allgemeinen 1,0 bis 2,5To carry out process (b) according to the invention, generally 1.0 to 2.5 are employed per mole in 1-arylpyrazole of the formula (III) substituted in the 4-position
Mol, vorzugsweise 1,0 bis 1,5 Mol an Sulfenylhalogenid der Formel (IV) und gegebenenfalls 1,0 bis 2,5 Mol, vorzugsweise 1,0 bis 1,5 Mol an Reaktionshilfsmittel ein. Die Reaktionsführung, Aufarbeitung und Isolierung der Reaktionsprodukte erfolgt nach allgemein üblichen Verfahren.Mol, preferably 1.0 to 1.5 mol of sulfenyl halide of the formula (IV) and optionally 1.0 to 2.5 mol, preferably 1.0 to 1.5 mol of reaction auxiliaries. The reaction, working up and isolation of the reaction products is carried out according to generally customary methods.
Als Oxidationsmittel zur Durchführung des erfindungsgemäßen Verfahrens (c) kommen alle üblichen zur Schwefeloxidation verwendbaren Oxidationsmittel infrage. Insbesondere geeignet sind Wasserstoffperoxid, organische Persäuren, wie beispielsweise Peressigsäure, m-Chlorperbenzoesäure, p-Nitroperbenzoesäure oder Luftsauerstoff. Als Verdünnungsmittel zur Durchführung des erfindungsgemäßen Verfahrens (c)- kommen ebenfalls inerte organische Lösungsmittel infrage. Vorzugsweise verwendet man Kohlenwasserstoffe, wie Benzin, Benzol, Toluol, Hexan oder Petrolether; chlorierte Kohlenwasserstoffe, wie Dichlormethan, 1 ,2-Dichlorethan, Chloroform, Tetra- chlorkohlenstoff oder Chlorbenzol; Ether, wie Diethylether, Dioxan oder Tetrahydro- furan; Carbonsäuren, wie Essigsäure oder Propionsäure, oder dipolare aprotische Lösungsmittel, wie Acetonitril, Aceton, Essigsäureethylester oder Dimethylform- amid.Suitable oxidizing agents for carrying out process (c) according to the invention are all customary oxidizing agents which can be used for sulfur oxidation. Hydrogen peroxide, organic peracids such as peracetic acid, m-chloroperbenzoic acid, p-nitroperbenzoic acid or atmospheric oxygen are particularly suitable. Inert organic solvents are also suitable as diluents for carrying out process (c) according to the invention. Hydrocarbons, such as gasoline, benzene, toluene, hexane or petroleum ether, are preferably used; chlorinated hydrocarbons, such as dichloromethane, 1, 2-dichloroethane, chloroform, carbon tetrachloride or chlorobenzene; Ethers, such as diethyl ether, dioxane or tetrahydrofuran; Carboxylic acids, such as acetic acid or propionic acid, or dipolar aprotic solvents, such as acetonitrile, acetone, ethyl acetate or dimethylformamide.
Das erfindungsgemäße Verfahren (c) kann gegebenenfalls in Gegenwart eines Säurebindemittels durchgeführt werden. Als solche kommen alle üblicherweise verwendbaren organischen und anorganischen Säurebindemittel infrage. Vorzugsweise verwendet man Erdalkali- oder Alkalimetallhydroxide, -acetate oder -carbonate, wie beispielsweise Calciumhydroxcid, Natriumhydroxid, Natriumacetat oder Natrium- carbonat.If appropriate, process (c) according to the invention can be carried out in the presence of an acid binder. As such, all commonly used organic and inorganic acid binders come into question. Alkaline earth metal or alkali metal hydroxides, acetates or carbonates, such as calcium hydroxide, sodium hydroxide, sodium acetate or sodium carbonate, are preferably used.
Das erfmdungsgemäße Verfahren (c) kann gegebenenfalls in Gegenwart eines geeigneten Katalysators durchgeführt werden. Als solche kommen alle üblicherweise für derartige Schwefeloxidationen gebräuchlichen Metallsalz-Katalysatoren infrage. Bei- spielhaft genannt seien Ammoniummolybdat und Natriumwolframat.If appropriate, process (c) according to the invention can be carried out in the presence of a suitable catalyst. All metal salt catalysts customarily used for such sulfur oxidations are suitable as such. Examples include ammonium molybdate and sodium tungstate.
Die Reaktionstemperaturen können bei der Durchführung des erfindungsgemäßen Verfahrens (c) in einem größeren Bereich variiert werden. Im allgemeinen arbeitet man bei Temperaturen zwischen -20°C und +70°C. vorzugsweise bei Temperaturen zwischen 0°C und +50°C.The reaction temperatures can be varied within a substantial range when carrying out process (c) according to the invention. Generally one works at temperatures between -20 ° C and + 70 ° C. preferably at temperatures between 0 ° C and + 50 ° C.
Zur Durchführung des erfindungsgemäßen Verfahrens (c) setzt man pro Mol an Verbindung der Formel (Ia) im allgemeinen 0,8 bis 1 ,2 Mol, vorzugsweise äquimolare Mengen Oxidationsmittel ein, wenn man die Oxidation des Schwefels auf der Sulf- oxidstufe unterbrechen will. Zur Oxidation zum Sulfon setzt man pro Mol an Verbindung der Formel (Ia) im allgemeinen 1,8 bis 3,0 Mol, vorzugsweiae doppelt molare Mengen an Oxidationsmittel ein. Die Reaktionsdurchführung, Aufarbeitung^ und Isolierung der Endprodukte erfolgt nach üblichen Verfahren.To carry out process (c) according to the invention, 0.8 to 1.2 moles, preferably equimolar amounts, of oxidizing agent are generally used per mole of compound of the formula (Ia) if one wishes to interrupt the oxidation of the sulfur at the sulfoxide stage. For oxidation to the sulfone, 1.8 to 3.0 mol, preferably twice, are generally employed per mole of compound of the formula (Ia) molar amounts of oxidizing agent. The reaction, workup and isolation of the end products is carried out by customary methods.
Erfindungsgemäße substituierte 3-Thiocarbamoylpyrazole der Formel (Ia) können gegebenenfalls auch erhalten werden, wenn man 3-Thiocarbamoyl-4-thiocyanato- pyrazole der Formel (Ib)Substituted 3-thiocarbamoylpyrazoles of the formula (Ia) according to the invention can also optionally be obtained if 3-thiocarbamoyl-4-thiocyanato-pyrazoles of the formula (Ib)
in welcher in which
Ar und R3 die oben angegebene Bedeutung haben,Ar and R 3 have the meaning given above,
mit Halogeniden der Formel (VI)with halides of the formula (VI)
Hal-R2 (VI),Hal-R 2 (VI),
in welcherin which
Hai und R2 die oben angegebene Bedeutung haben,Shark and R 2 have the meaning given above,
in allgemein üblicher Art und Weise in Gegenwart eines Verdünnungsmittels, wie insbesondere einem Alkohol (vorzugsweise Ethanol)/Wasser-Gemisch. bei Temperaturen zwischen -80°C und 50°C, vorzugsweise zwischen -50°C und Raumtemperatur umsetzt, wobei das Halogenid der Formel (VI) vorzugsweise in äquimolarer Menge, gegebenenfalls auch in einem leichten Überschuß eingesetzt wird. Die Wirkstoffe eignen sich bei guter Pflanzenverträglichkeit und günstiger Warm— blütertoxizität zur Bekämpfung von tierischen Schädlingen, insbesondere Insekten, Spinnentieren und Nematoden, die in der Landwirtschaft, in Forsten, im Vorrats- und Materialschutz sowie auf dem Hygienesektor vorkommen. Sie können vorzugsweise als Pflanzenschutzmittel eingesetzt werden. Sie sind gegen normal sensible und resi- stente Arten sowie gegen alle oder einzelne Entwicklungsstadien wirksam. Zu den oben erwähnten Schädlingen gehören:in a generally customary manner in the presence of a diluent, in particular an alcohol (preferably ethanol) / water mixture. at temperatures between -80 ° C and 50 ° C, preferably between -50 ° C and room temperature, wherein the halide of formula (VI) is preferably used in an equimolar amount, optionally also in a slight excess. With good plant tolerance and favorable warm-blood toxicity, the active substances are suitable for controlling animal pests, in particular insects, arachnids and nematodes, which occur in agriculture, in forests, in the protection of stored goods and materials, and in the hygiene sector. They can preferably be used as pesticides. They are effective against normally sensitive and resistant species as well as against all or individual stages of development. The pests mentioned above include:
Aus der Ordnung der Isopoda z.B. Oniscus asellus, Armadillidium vulgäre, Porcellio scaber.From the order of the Isopoda e.g. Oniscus asellus, Armadillidium vulgare, Porcellio scaber.
Aus der Ordnung der Diplopoda z.B. Blaniulus guttulatus.From the order of the Diplopoda e.g. Blaniulus guttulatus.
Aus der Ordnung der Chilopoda z.B. Geophilus carpophagus, Scutigera spec.From the order of the Chilopoda e.g. Geophilus carpophagus, Scutigera spec.
Aus der Ordnung der Symphyla z.B. Scutigerella immaculata.From the order of the Symphyla e.g. Scutigerella immaculata.
Aus der Ordnung der Thysanura z.B. Lepisma saccharina.From the order of the Thysanura e.g. Lepisma saccharina.
Aus der Ordnung der Collembola z.B. Onychiurus armatus.From the order of the Collembola e.g. Onychiurus armatus.
Aus der Ordnung der Orthoptera z.B. Blatta orientalis, Periplaneta americana, Leu- cophaea maderae, Blattella germanica, Acheta domesticus, Gryllotalpa spp., Locusta migratoria migratorioides, Melanoplus differentialis, Schistocerca gregaria.From the order of the Orthoptera e.g. Blatta orientalis, Periplaneta americana, Leucophaea maderae, Blattella germanica, Acheta domesticus, Gryllotalpa spp., Locusta migratoria migratorioides, Melanoplus differentialis, Schistocerca gregaria.
Aus der Ordnung der Dermaptera z.B. Forficula auricularia.From the order of the Dermaptera e.g. Forficula auricularia.
Aus der Ordnung der Isoptera z.B. Reticulitermes spp..From the order of the Isoptera e.g. Reticulitermes spp ..
Aus der Ordnung der Anoplura z.B. Pediculus humanus corporis, Haematopinus spp., Linognathus spp. Aus der Ordnung der Mallophaga z.B. Trichodectes spp., Damalinea spp.From the order of the anoplura, for example Pediculus humanus corporis, Haematopinus spp., Linognathus spp. From the order of the Mallophaga, for example Trichodectes spp., Damalinea spp.
Aus der Ordnung der Thysanoptera z.B. Hercinothrips femoralis, Thrips tabaci.From the order of the Thysanoptera e.g. Hercinothrips femoralis, Thrips tabaci.
Aus der Ordnung der Heteroptera z.B. Eurygaster spp., Dysdercus intermedius, Piesma quadrata, Cimex lectularius, Rhodnius prolixus, Triatoma spp.From the order of the Heteroptera e.g. Eurygaster spp., Dysdercus intermedius, Piesma quadrata, Cimex lectularius, Rhodnius prolixus, Triatoma spp.
Aus der Ordnung der Homoptera z.B. Aleurodes brassicae, Bemisia tabaci, Trialeu- rodes vaporariorum, Aphis gossypii, Brevicoryne brassicae, Cryptomyzus ribis,From the order of the Homoptera e.g. Aleurodes brassicae, Bemisia tabaci, Trialeurodes vaporariorum, Aphis gossypii, Brevicoryne brassicae, Cryptomyzus ribis,
Aphis fabae, Aphis pomi, Eriosoma lanigerum, Hyalopterus arundinis, Phylloxera vastatrix, Pemphigus spp., Macrosiphum avenae, Myzus spp., Phorodon humuli, Rhopalosiphum padi, Empoasca spp., Euscelis bilobatus, Nephotettix cincticeps, Lecanium corni, Saissetia oleae, Laodelphax striatellus, Nilaparvata lugens, Aonidiella aurantii, Aspidiotus hederae, Pseudococcus spp., Psylla spp.Aphis fabae, aphis pomi, eriosoma lanigerum, hyalopterus arundinis, phylloxera vastatrix, pemphigus spp., Macrosiphum avenae, myzus spp., Phorodon humuli, rhopalosiphum padi, empoasca spp , Nilaparvata lugens, Aonidiella aurantii, Aspidiotus hederae, Pseudococcus spp., Psylla spp.
Aus der Ordnung der Lepidoptera z.B. Pectinophora gossypiella, Bupalus piniarius, Cheimatobia brumata, Lithocolletis blancardella, Hyponomeuta padella, Plutella maculipennis, Malacosoma neustria, Euproctis chrysorrhoea, Lymantria spp., Bucculatrix thurberiella, Phyllocnistis citrella, Agrotis spp., Euxoa spp., Feltia spp.,From the order of the Lepidoptera e.g. Pectinophora gossypiella, Bupalus piniarius, Cheimatobia brumata, Lithocolletis blancardella, Hyponomeuta padella, Plutella maculipennis, Malacosoma neustria, Euproctis chrysorrhoea, Lymantria spp., Bucculatrix thurberiisispppp., Phyllocnistia. Phyllocnist.
Earias insulana, Heliothis spp., Spodoptera exigua, Mamestra brassicae, Panolis flammea, Spodoptera litura, Spodoptera spp., Trichoplusia ni, Carpocapsa pomo- nella, Pieris spp., Chilo spp., Pyrausta nubilalis, Ephestia kuehniella, Galleria mellonella, Tineola bisselliella, Tinea pellionella, Hofmannophila pseudospretella, Cacoecia podana, Capua reticulana, Choristoneura fumiferana, Clysia ambiguella,Earias insulana, Heliothis spp., Spodoptera exigua, Mamestra brassicae, Panolis flammea, Spodoptera litura, Spodoptera spp., Trichoplusia ni, Carpocapsa pomonella, Pieris spp., Chilo spp., Pyrausta nubilalis, Ephestia kellaelliehnelliaellaellaiellaella bella , Tinea pellionella, Hofmannophila pseudospretella, Cacoecia podana, Capua reticulana, Choristoneura fumiferana, Clysia ambiguella,
Homona magnanima, Tortrix viridana.Homona magnanima, Tortrix viridana.
Aus der Ordnung der Coleoptera z.B. Anobium punctatum, Rhizopertha dominica,From the order of the Coleoptera e.g. Anobium punctatum, Rhizopertha dominica,
Bruchidius obtectus, Acanthoscelides obtectus, Hylotrupes bajulus, Agelastica alni, Leptinotarsa decemlineata, Phaedon cochleariae, Diabrotica spp., Psylliodes chry- socephala, Epilachna varivestis, Atomaria spp., Oryzaephilus surinamensis, Antho- nomus spp., Sitophilus spp., Otiorrhynchus sulcatus, Cosmopolites sordidus,^ Ceuthorrhynchus assimilis, Hypera postica, Dermestes spp., Trogoderma spp., Anthrenus spp., Attagenus spp., Lyctus spp., Meligethes aeneus, Ptinus spp., Niptus hololeucus, Gibbium psylloides, Tribolium spp., Tenebrio molitor. Agriotes spp., Conoderus spp., Melolontha melolontha, Amphimallon solstitialis, Costelytra zealandica.Bruchidius obtectus, Acanthoscelides obtectus, Hylotrupes bajulus, Agelastica alni, Leptinotarsa decemlineata, Phaedon cochleariae, Diabrotica spp., Psylliodes chry- socephala, Epilachna varivestis, Atomaria spp., Anthinamensisilus nomus spp., Sitophilus spp., Otiorrhynchus sulcatus, Cosmopolites sordidus, ^ Ceuthorrhynchus assimilis, Hypera postica, Dermestes spp., Trogoderma spp., Anthrenus spp., Attagenus spp., Lyctus spp., Meliginusus seneus , Gibbium psylloides, Tribolium spp., Tenebrio molitor. Agriotes spp., Conoderus spp., Melolontha melolontha, Amphimallon solstitialis, Costelytra zealandica.
Aus der Ordnung der Hymenoptera z.B. Diprion spp., Hoplocampa spp., Lasius spp., Monomorium pharaonis, Vespa spp.From the order of the Hymenoptera e.g. Diprion spp., Hoplocampa spp., Lasius spp., Monomorium pharaonis, Vespa spp.
Aus der Ordnung der Diptera z.B. Aedes spp., Anopheles spp., Culex spp., Drosophila melanogaster, Musca spp., Fannia spp., Calliphora erythrocephala, Lucilia spp., Chrysomyia spp., Cuterebra spp., Gastrophilus spp., Hyppobosca spp., Stomoxys spp., Oestrus spp., Hypoderma spp., Tabanus spp., Tannia spp., Bibio hortulanus, Oscinella frit, Phorbia spp., Pegomyia hyoscyami, Ceratitis capitata,From the order of the Diptera e.g. Aedes spp., Anopheles spp., Culex spp., Drosophila melanogaster, Musca spp., Fannia spp., Calliphora erythrocephala, Lucilia spp., Chrysomyia spp., Cuterebra spp., Gastrophilus spp., Hyppobosca spp., Stomoxys Oestrus spp., Hypoderma spp., Tabanus spp., Tannia spp., Bibio hortulanus, Oscinella frit, Phorbia spp., Pegomyia hyoscyami, Ceratitis capitata,
Dacus oleae, Tipula paludosa.Dacus oleae, Tipula paludosa.
Aus der Ordnung der Siphonaptera z.B. Xenopsylla cheopis, Ceratophyllus spp..From the order of the Siphonaptera e.g. Xenopsylla cheopis, Ceratophyllus spp ..
Aus der Ordnung der Arachnida z.B. Scorpio maurus, Latrodectus mactans.From the order of the Arachnida e.g. Scorpio maurus, Latrodectus mactans.
Aus der Ordnung der Acarina z.B. 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..From the order of the 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 ., Tarsonemus spp., Bryobia praetiosa, Panonychus spp., Tetranychus spp ..
Zu den pflanzenparasitären Nematoden gehören z.B. Pratylenchus spp., Radopholus similis, Ditylenchus dipsaci, Tylenchulus semipenetrans, Heterodera spp., Globodera spp., Meloidogyne spp., Aphelenchoides spp., Longidorus spp., Xiphinema spp.,Plant-parasitic nematodes include e.g. Pratylenchus spp., Radopholus similis, Ditylenchus dipsaci, Tylenchulus semipenetrans, Heterodera spp., Globodera spp., Meloidogyne spp., Aphelenchoides spp., Longidorus spp., Xiphinema spp.,
Trichodorus spp.. Die erfindungsgemäßen Verbindungen der Formel (I) zeichnen sich insbesondere durch eine hohe insektizide Wirksamkeit aus. Sie lassen sich mit besonders gutem Erfolg zur Bekämpfung von pflanzenschädigenden Insekten, wie beispielsweise gegen die Raupen des Eulenfalters (Spodoptera frugiperda) oder die PfirsichblattlausTrichodorus spp .. The compounds of the formula (I) according to the invention are notable in particular for their high insecticidal activity. They can be used with particularly good success in combating plant-damaging insects, such as, for example, against the caterpillars of the owl butterfly (Spodoptera frugiperda) or the peach aphid
(Mycus persicae) einsetzen.(Mycus persicae).
Die Wirkstoffe können in die üblichen Formulierungen überfuhrt werden, wie Lösungen, Emulsionen, Spritzpulver, Suspensionen, Pulver, Stäubemittel, Pasten, lösliche Pulver, Granulate, Suspensions-Emulsions-Konzentrate, Wirkstoff-imprägnierteThe 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, impregnated with active compounds
Natur- und synthetische Stoffe sowie Feinstverkapselungen in polymeren Stoffen.Natural and synthetic substances as well as very fine encapsulation in polymeric substances.
Diese Formulierungen werden in bekannter Weise hergestellt, z.B. durch Vermischen der Wirkstoffe mit Streckmitteln, also flüssigen Lösungsmitteln und/oder festen Trä- gerstoffen, gegebenenfalls unter Verwendung von oberflächenaktiven Mitteln, alsoThese formulations are made in a known manner, e.g. by mixing the active ingredients with extenders, that is to say liquid solvents and / or solid carriers, if appropriate using surface-active agents, that is to say
Emulgiermitteln und/oder Dispergiermitteln und/oder schaumerzeugenden Mitteln.Emulsifiers and / or dispersants and / or foaming agents.
Im Falle der Benutzung von Wasser als Streckmittel können z.B. auch organische Lösungsmittel als Hilfslösungsmittel verwendet werden. Als flüssige Lösungsmittel kommen im wesentlichen in Frage: Aromaten, wie Xylol, Toluol, oder Alkylnaph- thaline, chlorierte Aromaten und chlorierte aliphatische Kohlenwasserstoffe, wie Chlorbenzole, Chlorethylene oder Methylenchlorid, aliphatische Kohlenwasserstoffe, wie Cyclohexan oder Paraffine, z.B. Erdölfraktionen, mineralische und pflanzliche Öle, Alkohole, wie Butanol oder Glykol sowie deren Ether und Ester, Ketone wie Aceton, Methylethylketon, Methylisobutylketon oder Cyclohexanon, stark polareIf water is used as an extender, e.g. organic solvents can also be used as auxiliary solvents. The following are essentially suitable as liquid solvents: aromatics, such as xylene, toluene, or alkylnaphthalenes, chlorinated aromatics and chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chlorethylenes or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, e.g. Petroleum fractions, mineral and vegetable oils, alcohols such as butanol or glycol and their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar
Lösungsmittel, wie Dimethylformamid und Dimethylsulfoxid, sowie Wasser.Solvents such as dimethylformamide and dimethyl sulfoxide, and water.
Als feste Trägerstoffe kommen in Frage:The following are suitable as solid carriers:
z.B. Ammoniumsalze und natürliche Gesteinsmehle, wie Kaoline, Tonerden, Talkum, Kreide, Quarz, Attapulgit, Montmorillonil oder Diatomeenerde und synthe- tische Gesteinsmehle, wie hochdisperse Kieselsäure, Aluminiumoxid und Silikate,- als feste Trägerstoffe für Granulate kommen in Frage: z.B. gebrochene und fraktionierte natürliche Gesteine wie Calcit, Marmor, Bims, Sepiolith, Dolomit sowie synthetische Granulate aus anorganischen und organischen Mehlen sowie Granulate aus organischem Material wie Sägemehl, Kokosnußschalen, Maiskolben und Tabakstengeln; als Emulgier- und oder schaumerzeugende Mittel kommen in Frage: z.B. nichtionogene und anionische Emulgatoren, wie Polyoxyethylen-Fettsäure-Ester, Polyoxyethylen-Fettalkohol-Ether, z.B. Alkylaryl-polyglykolether, Alkylsulfonate, Alkylsulfate, Arylsulfonate sowie Einweißhydrolysate; als Dispergiermittel kommen in Frage: z.B. Lignin-Sulfitablaugen und Methylcellulose.eg ammonium salts and natural rock powder, such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonil or diatomaceous earth and synthetic table stone powders such as highly disperse silica, aluminum oxide and silicates, - are suitable as solid carriers for granules: 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; suitable emulsifying and or foam-generating agents are: for example nonionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates and protein hydrolyzates; Possible dispersing agents are, for example, lignin sulfite waste liquor and methyl cellulose.
Es können in den Formulierungen Haftmittel wie Carboxymethylcellulose, natürliche und synthetische pulvrige, körnige oder latexförmige Polymere verwendet werden, wie Gummiarabicum, Polyvinylalkohol, Polyvinylacetat, sowie natürliche Phospho- lipide, wie Kephaline und Lecithine und synthetische Phospholipide. Weitere Additive können mineralische und vegetabile Öle sein.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.
Es können Farbstoffe wie anorganische Pigmente, z.B. Eisenoxid, Titanoxid, Ferro- cyanblau und organische Farbstoffe, wie Alizarin-, Azo- und Metallphthalocyanin- farbstoffe und Spurennährstoffe wie Salze von Eisen, Mangan, Bor, Kupfer, Kobalt,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,
Molybdän und Zink verwendet werden.Molybdenum and zinc can be used.
Die Formulierungen enthalten im allgemeinen zwischen 0,1 und 95 Gew.-% Wirkstoff, vorzugsweise zwischen 0,5 und 90 %.The formulations generally contain between 0.1 and 95% by weight of active compound, preferably between 0.5 and 90%.
Der erfindungsgemäße Wirkstoff kann in seinen handelsüblichen Formulierungen sowie in den aus diesen Formulierungen bereiteten Anwendungsformen in Mischung mit anderen Wirkstoffen, wie Insektiziden, Lockstoffen, Sterilantien, Bakteriziden, Akariziden, Nematiziden, Fungiziden, wachstumsregulierenden Stoffen oder Herbi- ziden vorliegen. Zu den Insektiziden zählen beispielsweise Phosphorsäureester, Carbamate, Carbonsäureester, chlorierte Kohlenwasserstoffe, Phenylharnstoffe,- durch Mikroorganismen hergestellte Stoffe u.a.The active substance according to the invention can be present in its commercially available formulations and in the use forms prepared from these formulations in a mixture with other active substances, such as insecticides, attractants, sterilants, bactericides, acaricides, nematicides, fungicides, growth-regulating substances or herbicides. Insecticides include, for example, phosphoric acid esters, Carbamates, carboxylic acid esters, chlorinated hydrocarbons, phenylureas, - substances produced by microorganisms etc.
Besonders günstige Mischpartner sind z.B. die folgenden:Particularly cheap mixing partners are e.g. the following:
Fungizide:Fungicides:
Aldimorph, Ampropylfos, Ampropylfos-Kalium, Andoprim, Anilazin, Azaconazol, Azoxystrobin,Aldimorph, ampropylfos, ampropylfos potassium, andoprim, anilazine, azaconazole, azoxystrobin,
Benalaxyl, Benodanil, Benomyl, Benzamacril, Benzamacryl-isobutyl, Bialaphos, Binapacryl, Biphenyl, Bitertanol, Blasticidin-S, Bromuconazol, Bupirimat, Buthiobat,Benalaxyl, benodanil, benomyl, benzamacril, benzamacrylic isobutyl, bialaphos, binapacrylic, biphenyl, bitertanol, blasticidin-S, bromuconazole, bupirimate, buthiobate,
Calciumpolysulfid, Capsimycin, Captafol, Captan, Carbendazim, Carboxin, Carvon, Chinomethionat (Quinomethionat), Chlobenthiazon, Chlorfenazol, Chloroneb, Chloro- picrin, Chlorothalonil, Chlozolinat, Clozylacon, Cufraneb, Cymoxanil, Cyproconazol, Cyprodinil, Cyprofuram,Calcium polysulfide, capsimycin, captafol, captan, carbendazim, carboxin, carvone, quinomethionate (quinomethionate), chlobenthiazone, chlorfenazole, chloroneb, chloropicrin, chlorothalonil, chlozolinate, clozylacon, cufraneb, cymoxanil, cyphodaminazol, cypodaminazol, cypodinconol
Debacarb, Dichlorophen, Diclobutrazol, Diclofluanid, Diclomezin, Dicloran, Diethofencarb, Difenoconazol, Dimethirimol, Dimethomoφh, Diniconazol,Debacarb, dichlorophene, diclobutrazole, diclofluanide, diclomezin, dicloran, diethofencarb, difenoconazole, dimethirimol, dimethomoφh, diniconazole,
Diniconazol-M, Dinocap, Diphenylamin, Dipyrithione, Ditalimfos, Dithianon, Dodemorph, Dodine, Drazoxolon,Diniconazol-M, Dinocap, Diphenylamine, Dipyrithione, Ditalimfos, Dithianon, Dodemorph, Dodine, Drazoxolon,
Ediphenphos, Epoxiconazol, Etaconazol, Ethirimol, Etridiazol,Ediphenphos, Epoxiconazole, Etaconazole, Ethirimol, Etridiazole,
Famoxadon, Fenapanil, Fenarimol, Fenbuconazol, Fenfuram, Fenitropan, Fenpiclonil, Fenpropidin, Fenpropimoφh, Fentinacetat, Fentinhydroxyd, Ferbam, Ferimzon, Fluazinam, Flumetover, Fluoromid, Fluquinconazol, Fluφrimidol, Flusilazol, Flusulfamid, Flutolanil, Flutriafol, Folpet, Fosetyl-Alminium, Fosetyl-Natrium, Fthalid, Fuberidazol, Furalaxyl, Furametpyr, Furcarbonil, Furconazol, Furconazol-cis,Famoxadon, Fenapanil, Fenarimol, Fenbuconazol, Fenfuram, Fenitropan, Fenpiclonil, Fenpropidin, Fenpropimoφh, Fentinacetat, Fentinhydroxyd, Ferbam, Ferimzon, Fluazinam, Flumetover, Fluoromid, Fluquinconazol, Fluφrimidol, Flusrimidol, Flusrimidol, Flusrilidol, Flusrilidol, Flusrilidol, Flusrilidol, Flusrilidol, Fosetyl sodium, fthalide, fuberidazole, furalaxyl, furametpyr, furcarbonil, furconazole, furconazole-cis,
Furmecyclox, Guazatin,Furmecyclox, Guazatin,
Hexachlorobenzol, Hexaconazol, Hymexazol,Hexachlorobenzene, hexaconazole, hymexazole,
Imazalil, Imibenconazol, Iminoctadin, Iminoctadinealbesilat, Iminoctadinetriacetat, lodocarb, Ipconazol, Iprobenfos (IBP), Iprodione, Irumamycin, Isoprothiolan, Isovaledione,Imazalil, Imibenconazol, Iminoctadin, Iminoctadinealbesilat, Iminoctadinetriacetat, Iodocarb, Ipconazol, Iprobefos (IBP), Iprodione, Irumamycin, Isoprothiolan, Isovaledione,
Kasugamycin, Kresoxim-methyl, Kupfer-Zubereitungen, wie: Kupferhydroxid,Kasugamycin, Kresoxim-methyl, copper preparations such as: copper hydroxide,
Kupfemaphthenat, Kupferoxychlorid, Kupfersulfat, Kupferoxid, Oxin-Kupfer und Bordeaux-Mischung,Copper phthalate, copper oxychloride, copper sulfate, copper oxide, oxine-copper and Bordeaux mixture,
Mancopper, Mancozeb, Maneb, Meferimzone, Mepanipyrim, Mepronil, Metalaxyl, Metconazol, Methasulfocarb, Methfuroxam, Metiram, Metomeclam, Metsulfovax,Mancopper, Mancozeb, Maneb, Meferimzone, Mepanipyrim, Mepronil, Metalaxyl, Metconazol, Methasulfocarb, Methfuroxam, Metiram, Metomeclam, Metsulfovax,
Mildiomycin, Myclobutanil, Myclozolin,Mildiomycin, myclobutanil, myclozolin,
Nickel-dimethyldithiocarbamat, Nitrothal-isopropyl, Nuarimol,Nickel dimethyldithiocarbamate, nitrothal isopropyl, Nuarimol,
Ofurace, Oxadixyl, Oxamocarb, Oxolinicacid, Oxycarboxim, Oxyfenthiin,Ofurace, Oxadixyl, Oxamocarb, Oxolinicacid, Oxycarboxim, Oxyfenthiin,
Paclobutrazol, Pefurazoat, Penconazol, Pencycuron, Phosdiphen, Pimaricin, Piperalin, Polyoxin, Polyoxorim, Probenazol, Prochloraz, Procymidon, Propamocarb, Propanosine-Natrium, Propiconazol, Propineb, Pyrazophos, Pyrifenox. Pyrimethanil, Pyroquilon, Pyroxyfur,Paclobutrazole, pefurazoate, penconazole, pencycuron, phosdiphen, pimaricin, piperalin, polyoxin, polyoxorim, probenazole, prochloraz, procymidone, propamocarb, propanosine sodium, propiconazole, propineb, pyrazophos, pyrifenox. Pyrimethanil, pyroquilon, pyroxyfur,
Quinconazol, Quintozen (PCNB),Quinconazole, quintozen (PCNB),
Schwefel und Schwefel-Zubereitungen. Tebuconazol, Tecloftalam, Tecnazen, Tetcyclacis, Tetraconazol, Thiabendazol, Thicyofen, Thifluzamide, Thiophanate-methyl, Thiram, Tioxymid, Tolclofos-methyl, Tolylfluanid, Triadimefon, Triadimenol, Triazbutil, Triazoxid, Trichlamid, Tricyclazol, Tridemoφh, Triflumizol, Triforin, Triticonazol,Sulfur and sulfur preparations. Tebuconazole, tecloftalam, tecnazene, Tetcyclacis, tetraconazole, thiabendazole, Thicyofen, Thifluzamide, thiophanate-methyl, thiram, Tioxymid, tolclofos-methyl, tolylfluanid, triadimefon, triadimenol, Triazbutil, triazoxide, Trichlamid, tricyclazole, Tridemoφh, triflumizole, triforine, triticonazole,
Uniconazol,Uniconazole,
Validamycin A, Vinclozolin, Viniconazol,Validamycin A, vinclozolin, viniconazole,
Zarilamid, Zineb, Ziram sowieZarilamid, Zineb, Ziram as well
Dagger G,Dagger G,
OK-8705,OK-8705,
OK-8801, α-( 1 , 1 -Dimethylethyl)-ß-(2-phenoxyethy 1)- 1 H- 1 ,2,4-triazol- 1 -ethanol, α-(2,4-Dichlθφhenyl)-ß-fluor-b-propyl- 1 H- 1 ,2,4-triazol- 1 -ethanol, α-(2,4-Dichlθφhenyl)-ß-methoxy-a-methyl- 1 H- 1 ,2,4-triazol- 1 -ethanol, α-(5-Methyl- 1 ,3-dioxan-5-yl)-ß-[[4-(trifluormethyl)-phenyl]-methylen]- 1 H- 1 ,2,4- triazol-1 -ethanol, (5RS,6RS)-6-Hydroxy-2,2,7,7-tetramethyl-5-( 1 H- 1 ,2,4-triazol- 1 -yl)-3-octanon,OK-8801, α- (1, 1-dimethylethyl) -ß- (2-phenoxyethy 1) - 1 H- 1, 2,4-triazole-1-ethanol, α- (2,4-dichloro phhenyl) -ß- fluoro-b-propyl-1 H-1, 2,4-triazole-1-ethanol, α- (2,4-dichloro phhenyl) -ß-methoxy-a-methyl- 1 H-1, 2,4-triazole- 1-ethanol, α- (5-methyl-1, 3-dioxan-5-yl) -ß - [[4- (trifluoromethyl) phenyl] methylene] - 1 H-1, 2,4-triazol-1 -ethanol, (5RS, 6RS) -6-hydroxy-2,2,7,7-tetramethyl-5- (1 H-1, 2,4-triazol-1-yl) -3-octanone,
(E)-a-(Methoxyimino)-N-methyl-2-phenoxy-phenylacetamid,(E) -a- (methoxyimino) -N-methyl-2-phenoxy-phenylacetamide,
{2-Methyl-l-[[[l-(4-methylphenyl)-ethyl]-amino]-carbonyl]-propyl}-carbaminsäure-l- isopropylester{2-Methyl-l - [[[l- (4-methylphenyl) ethyl] amino] carbonyl] propyl} carbamic acid l-isopropyl ester
1 -(2,4-Dichlθφhenyl)-2-( 1 H- 1 ,2,4-triazol- 1 -yl)-ethanon-O-(pheny lmethy l)-oxim. 1 -(2-Methyl-l -naphthalenyl)- 1 H-pyrrol-2,5-dion, l-(3,5-Dichloφhenyl)-3-(2-propenyl)-2,5-pyrrolidindion, l-[(Diiodmethyl)-sulfonyl]-4-methyl-benzol, l-[[2-(2,4-Dichloφhenyl)-l ,3-dioxolan-2-yl]-methyl]-lH-imidazol, l-[[2-(4-Chlθφhenyl)-3-phenyloxiranyl]-methyl]-lH-l,2,4-triazol, l-[l-[2-[(2,4-Dichloφhenyl)-methoxy]-phenyl]-ethenyl]-l H-imidazol, l-Methyl-5-nonyl-2-(phenylmethyl)-3-pyrrolidinol, 2',6'-Dibrom-2-methyl-4,-trifluormethoxy-4'-trifluor-methyl-l,3-thiazol-5-carboxanilid,1 - (2,4-Dichlθφhenyl) -2- (1 H- 1, 2,4-triazol-1-yl) -ethanone-O- (phenylmethyl) oxime. 1 - (2-methyl-l-naphthalenyl) - 1 H-pyrrole-2,5-dione, l- (3,5-dichlorophenyl) -3- (2-propenyl) -2,5-pyrrolidinedione, l- [ (Diiodomethyl) sulfonyl] -4-methyl-benzene, l - [[2- (2,4-dichloφhenyl) -l, 3-dioxolan-2-yl] methyl] -lH-imidazole, l - [[2 - (4-Chlθφhenyl) -3-phenyloxiranyl] methyl] -lH-l, 2,4-triazole, l- [l- [2 - [(2,4-dichloφhenyl) methoxy] phenyl] ethenyl] -l H-imidazole, l-methyl-5-nonyl-2- (phenylmethyl) -3-pyrrolidinol, 2 ', 6'-dibromo-2-methyl-4 , -trifluoromethoxy-4'-trifluoromethyl-l, 3-thiazole-5-carboxanilide,
2,2-Dichlor-N-[l-(4-chloφhenyl)-ethyl]-l-ethyl-3-methyl-cyclopropancarboxamid,2,2-dichloro-N- [1- (4-chloro-phenyl) -ethyl] -l-ethyl-3-methyl-cyclopropanecarboxamide,
2,6-Dichlor-5-(methylthio)-4-pyrimidinyl-thiocyanat,2,6-dichloro-5- (methylthio) -4-pyrimidinyl-thiocyanate,
2,6-Dichlor-N-(4-trifluormethylbenzyl)-benzamid, 2,6-Dichlor-N-[[4-(trifluormethyl)-phenyl]-methyl]-benzamid,2,6-dichloro-N- (4-trifluoromethylbenzyl) benzamide, 2,6-dichloro-N - [[4- (trifluoromethyl) phenyl] methyl] benzamide,
2-(2,3,3-Triiod-2-propenyl)-2H-tetrazol,2- (2,3,3-triiodo-2-propenyl) -2H-tetrazole,
2-[(l -Methylethyl)-sulfonyl]-5-(trichlormethyl)- 1 ,3,4-thiadiazol,2 - [(1-methylethyl) sulfonyl] -5- (trichloromethyl) -1,3,4-thiadiazole,
2-[[6-Deoxy-4-O-(4-O-methyl-ß-D-glycopyranosyl)-a-D-glucopyranosyl]-amino]-4- methoxy-lH-pyrrolo[2,3-d]pyrimidin-5-carbonitril, 2-Aminobutan,2 - [[6-Deoxy-4-O- (4-O-methyl-ß-D-glycopyranosyl) -aD-glucopyranosyl] -amino] -4- methoxy-lH-pyrrolo [2,3-d] pyrimidine- 5-carbonitrile, 2-aminobutane,
2-Brom-2-(brommethyl)-pentandinitril,2-bromo-2- (bromomethyl) pentandinitrile,
2-Chlor-N-(2,3-dihydro-l,l,3-trimethyl-lH-inden-4-yl)-3-pyridincarboxamid,2-chloro-N- (2,3-dihydro-l, l, 3-trimethyl-lH-inden-4-yl) -3-pyridinecarboxamide,
2-Chlor-N-(2,6-dimethylphenyl)-N-(isothiocyanatomethyl)-acetamid,2-chloro-N- (2,6-dimethylphenyl) -N- (isothiocyanatomethyl) acetamide,
2-Phenylphenol(OPP), 3,4-Dichlor-l -[4-(difluormethoxy)-phenyl]- 1 H-pyrrol-2,5-dion,2-phenylphenol (OPP), 3,4-dichloro-l - [4- (difluoromethoxy) phenyl] - 1 H-pyrrole-2,5-dione,
3,5-Dichlor-N-[cyan[(l-methyl-2-propynyl)-oxy]-methyl]-benzamid,3,5-dichloro-N- [cyan [(1-methyl-2-propynyl) oxy] methyl] benzamide,
3-(l , 1 -Dimethylpropyl-1 -oxo-1 H-inden-2-carbonitril,3- (1,1-dimethylpropyl-1-oxo-1 H-indene-2-carbonitrile,
3-[2-(4-Chloφhenyl)-5-ethoxy-3-isoxazolidinyl]-pyridin,3- [2- (4-chloro-phenyl) -5-ethoxy-3-isoxazolidinyl] pyridine,
4-Chlor-2-cyan-N,N-dimethyl-5-(4-methylpheny 1)- 1 H-imidazol- 1 -sulfonamid, 4-Methyl-tetrazolo[l ,5-a]quinazolin-5(4H)-on,4-chloro-2-cyan-N, N-dimethyl-5- (4-methylpheny 1) - 1 H -imidazole-1 -sulfonamide, 4-methyl-tetrazolo [l, 5-a] quinazolin-5 (4H) -on,
8-( 1 , 1 -Dimethylethyl)-N-ethyl-N-propyl- 1 ,4-dioxaspiro[4.5]decan-2-methanamin,8- (1, 1-dimethylethyl) -N-ethyl-N-propyl-1, 4-dioxaspiro [4.5] decane-2-methanamine,
8-Hydroxychinolinsulfat,8-hydroxyquinoline sulfate,
9H-Xanthen-9-carbonsäure-2- [(pheny lamino)-carbony 1] -hydrazid, bis-(l-Methylethyl)-3-methyl-4-[(3-methylbenzoyl)-oxy]-2,5-thiophendicarboxylat, cis-l-(4-Chlθφhenyl)-2-(lH-l ,2,4-triazol-l -yl)-cycloheptanol, cis-4-[3-[4-(l,l-Dimethylpropyl)-phenyl-2-methylpropyl]-2,6-dimethyl-moφholin- hydrochlorid,9H-xanthene-9-carboxylic acid 2- [(phenyllamino) carbony 1] hydrazide, bis- (l-methylethyl) -3-methyl-4 - [(3-methylbenzoyl) -oxy] -2,5- thiophene dicarboxylate, cis-l- (4-chloro-phenyl) -2- (lH-l, 2,4-triazol-l -yl) -cycloheptanol, cis-4- [3- [4- (l, l-dimethylpropyl) - phenyl-2-methylpropyl] -2,6-dimethyl-moφholin hydrochloride,
Ethyl-[(4-chlθφhenyl)-azo]-cyanoacetat,Ethyl - [(4-chlθφhenyl) azo] cyanoacetate,
Kai iumhydrogencarbonat, Methantetrathiol-Natriumsalz,Kai ium hydrogen carbonate, methane tetrathiol sodium salt,
Methyl-l-(2,3-dihydro-2,2-dimethyl-lH-inden-l-yl)-lH-imidazol-5-carboxylat, Methyl-N-(2,6-dimethylphenyl)-N-(5-isoxazolylcarbonyl)-DL-alaninat,Methyl l- (2,3-dihydro-2,2-dimethyl-lH-inden-l-yl) -lH-imidazole-5-carboxylate, Methyl N- (2,6-dimethylphenyl) -N- (5-isoxazolylcarbonyl) -DL-alaninate,
Methyl-N-(chloracetyl)-N-(2,6-dimethylphenyl)-DL-alaninat,Methyl N- (chloroacetyl) -N- (2,6-dimethylphenyl) -DL-alaninate,
N-(2,3 -Dichlor-4-hydroxyphenyl)- 1 -methyl-cyclohexancarboxamid.N- (2,3-dichloro-4-hydroxyphenyl) -1-methyl-cyclohexane carboxamide.
N-(2,6-Dimethylphenyl)-2-methoxy-N-(tetrahydro-2-oxo-3-ftιranyl)-acetamid, N-(2,6-Dimethylphenyl)-2-methoxy-N-(tetrahydro-2-oxo-3-thienyl)-acetamid,N- (2,6-dimethylphenyl) -2-methoxy-N- (tetrahydro-2-oxo-3-ftιranyl) acetamide, N- (2,6-dimethylphenyl) -2-methoxy-N- (tetrahydro-2 -oxo-3-thienyl) -acetamide,
N-(2-Chlor-4-nitrophenyl)-4-methyl-3-nitro-benzolsulfonamid,N- (2-chloro-4-nitrophenyl) -4-methyl-3-nitro-benzenesulfonamide,
N-(4-Cyclohexylphenyl)- 1 ,4,5,6-tetrahydro-2-pyrimidinamin,N- (4-cyclohexylphenyl) - 1, 4,5,6-tetrahydro-2-pyrimidinamine,
N-(4-Hexylphenyl)- 1 ,4,5,6-tetrahydro-2-pyrimidinamin,N- (4-hexylphenyl) - 1, 4,5,6-tetrahydro-2-pyrimidinamine,
N-(5-Chlor-2-methylphenyl)-2-methoxy-N-(2-oxo-3-oxazolidinyl)-acetamid, N-(6-Methoxy)-3 -pyridinyl)-cyclopropancarboxamid,N- (5-chloro-2-methylphenyl) -2-methoxy-N- (2-oxo-3-oxazolidinyl) acetamide, N- (6-methoxy) -3-pyridinyl) cyclopropanecarboxamide,
N-[2,2,2-Trichlor- 1 -[(chloracetyl)-amino]-ethyl]-benzamid,N- [2,2,2-trichloro-1 - [(chloroacetyl) amino] ethyl] benzamide,
N-[3-Chlor-4,5-bis-(2-propinyloxy)-phenyl]-N'-methoxy-methanimidamid,N- [3-chloro-4,5-bis (2-propynyloxy) phenyl] -N'-methoxymanimidamide,
N-Formyl-N-hydroxy-DL-alanin -Natriumsalz,N-formyl-N-hydroxy-DL-alanine sodium salt,
O,O-Diethyl-[2-(dipropylamino)-2-oxoethyl]-ethylphosphoramidothioat, O-Methyl-S-phenyl-phenylpropylphosphoramidothioate,O, O-diethyl- [2- (dipropylamino) -2-oxoethyl] ethylphosphoramidothioate, O-methyl-S-phenyl-phenylpropylphosphoramidothioate,
S-Methyl- 1 ,2,3-benzothiadiazol-7-carbothioat, spiro[2H]- 1 -Benzopyran-2, 1 '(3'H)-isobenzofuran]-3'-on,S-methyl-1, 2,3-benzothiadiazole-7-carbothioate, spiro [2H] -1-benzopyran-2, 1 '(3'H) -isobenzofuran] -3'-one,
Bakterizide:Bactericides:
Bronopol, Dichlorophen, Nitrapyrin, Nickel-Dimethyldithiocarbamat, Kasugamycin, Octhilinon, Furancarbonsäure, Oxytetracyclin, Probenazol, Streptomycin, Tecloftalam, Kupfersulfat und andere Kupfer-Zubereitungen.Bronopol, dichlorophene, nitrapyrin, nickel dimethyldithiocarbamate, kasugamycin, octhilinone, furan carboxylic acid, oxytetracycline, probenazole, streptomycin, tecloftalam, copper sulfate and other copper preparations.
Insektizide / Akarizide / Nematizide:Insecticides / acaricides / nematicides:
Abamectin, AC 303 630, Acephat, Acrinathrin, Alanycarb, Aldicarb, Alphamethrin, Amitraz, Avermectin, AZ 60541, Azadirachtin, Azinphos A, Azinphos M, Azocy- clotin, Bacillus thuringiensis, Bendiocarb, Benfuracarb, Bensultap, Betacyfluthrin,- Bifenthrin, BPMC, Brofenprox, Bromophos A, Bufencarb, Buprofezin, Buto- carboxim, Butylpyridaben,Abamectin, AC 303 630, Acephat, Acrinathrin, Alanycarb, Aldicarb, Alphamethrin, Amitraz, Avermectin, AZ 60541, Azadirachtin, Azinphos A, Azinphos M, Azocyclotin, Bacillus thuringiensis, Bendiocarb, Benfuracarb, Bensultap, Betacyfluthrin, - Bifenthrin, BPMC, Brofenprox, Bromophos A, Bufencarb, Buprofezin, Butocarboxim, Butylpyridaben,
Cadusafos, Carbaryl, Carbofuran, Carbophenothion, Carbosulfan, Cartap, CGA 157 419, CGA 184699, Chloethocarb, Chlorethoxyfos, Chlorfenvinphos, Chlorfluazuron, Chlormephos, Chloφyrifos, Chloφyrifos M, Cis-Resmethrin, Clocythrin, Clofen- tezin, Cyanophos, Cycloprothrin, Cyfluthrin, Cyhalothrin, Cyhexatin, Cypermethrin, Cyromazin,Cadusafos, Carbaryl, Carbofuran, Carbophenothion, Carbosulfan, Cartap, CGA 157 419, CGA 184699, Chloethocarb, Chlorethoxyfos, Chlorfenvinphos, Chlorfluazuron, Chlormephos, Chloφyrifos, Chloφyrifos M, Cis-Resmethrin, Clyanothrinophin, Clyanothrin, Cyclin Cyhalothrin, cyhexatin, cypermethrin, cyromazine,
Deltamethrin, Demeton M, Demeton S, Demeton-S-methyl, Diafenthiuron, Diazinon, Dichlofenthion, Dichlorvos, Dicliphos, Dicrotophos, Diethion, Diflubenzuron, Dimethoat, Dimethylvinphos, Dioxathion, Disulfoton,Deltamethrin, Demeton M, Demeton S, Demeton-S-methyl, Diafenthiuron, Diazinon, Dichlofenthion, Dichlorvos, Dicliphos, Dicrotophos, Diethion, Diflubenzuron, Dimethoat, Dimethylvinphos, Dioxathion, Disulfoton,
Edifenphos, Emamectin, Esfenvalerat, Ethiofencarb, Ethion, Ethofenprox,Edifenphos, Emamectin, Esfenvalerat, Ethiofencarb, Ethion, Ethofenprox,
Ethoprophos, Etrimphos,Ethoprophos, Etrimphos,
Fenamiphos, Fenazaquin, Fenbutatinoxid, Fenitrothion, Fenobucarb, Fenothiocarb, Fenoxycarb, Fenpropathrin, Fenpyrad, Fenpyroximat, Fenthion, Fenvalerate, Fipronil, Fluazinam, Flucycloxuron, Flucythrinat, Flufenoxuron, Flufenprox, Fluva- linate, Fonophos, Formothion, Fosthiazat, Fubfenprox, Furathiocarb,Fenamiphos, Fenazaquin, Fenbutatinoxid, Fenitrothion, Fenobucarb, Fenothiocarb, Fenoxycarb, Fenpropathrin, Fenpyrad, Fenpyroximat, Fenthion, Fenvalerate, Fipronil, Fluazinam, Flucycloxuron, Flucythrinat, Flufenoxuron, Flufenproxatophon, Fufionphonophone, Fufionfox, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufone
HCH, Heptenophos, Hexaflumuron, Hexythiazox,HCH, heptenophos, hexaflumuron, hexythiazox,
Imidacloprid, Iprobenfos, Isazophos, Isofenphos, Isoprocarb, Isoxathion, Ivermectin,Imidacloprid, Iprobefos, Isazophos, Isofenphos, Isoprocarb, Isoxathion, Ivermectin,
Lambda-cyhalothrin, Lufenuron,Lambda cyhalothrin, lufenuron,
Malathion, Mecarbam, Mevinphos, Mesulfenphos, Metaldehyd, Methacrifos, Methamidophos, Methidathion, Methiocarb, Methomyl, Metolcarb, Milbemectin,Malathion, Mecarbam, Mevinphos, Mesulfenphos, Metaldehyde, Methacrifos, Methamidophos, Methidathion, Methiocarb, Methomyl, Metolcarb, Milbemectin,
Monocrotophos, Moxidectin, Naled, NC 184, NI 25, NitenpyramMonocrotophos, moxidectin, Naled, NC 184, NI 25, Nitenpyram
Omethoat, Oxamyl, Oxydemethon M, Oxydeprofos,Omethoate, Oxamyl, Oxydemethon M, Oxydeprofos,
Parathion A, Parathion M, Permethrin, Phenthoat, Phorat, Phosalon, Phosmet, Phos- phamidon, Phoxim, Pirimicarb, Pirimiphos M, Pirimiphos A, Profenofos, Promecarb, Propaphos, Propoxur, Prothiofos, Prothoat, Pymetrozin, Pyrachlophos, Pyridaphenthion, Pyresmethrin, Pyrethrum, Pyridaben, Pyrimidifen, Pyriproxifen,Parathion A, Parathion M, Permethrin, Phenthoat, Phorat, Phosalon, Phosmet, Phosphamidon, Phoxim, Pirimicarb, Pirimiphos M, Pirimiphos A, Profenofos, Promecarb, Propaphos, Propoxur, Prothiofos, Prothoat, Pymethionos, Pyridaphrinin, Pyridaphrinin, Pyridaphrinin Pyrethrum, Pyridaben, Pyrimidifen, Pyriproxifen,
Quinalphos,Quinalphos,
RH 5992,RH 5992,
Salithion, Sebufos, Silafluofen, Sulfotep, Sulprofos,Salithion, Sebufos, Silafluofen, Sulfotep, Sulprofos,
Tebufenozid, Tebufenpyrad, Tebupirimiphos, Teflubenzuron, Tefluthrin, Temephos, Terbam, Terbufos, Tetrachlorvinphos, Thiafenox, Thiodicarb, Thiofanox, Thiome- thon, Thionazin, Thuringiensin, Tralomethrin, Triarathen, Triazophos, Triazuron, Trichlorfon, Triflumuron, Trimethacarb,Tebufenozid, Tebufenpyrad, Tebupirimiphos, Teflubenzuron, Tefluthrin, Temephos, Terbam, Terbufos, Tetrachlorvinphos, Thiafenox, Thiodicarb, Thiofanox, Thiomethonon, Thionazin, Thuringiensin, Tralathenethronon, Tronomenhrononium, Tronomenhrononium, Tronomenhrononium, Tronomenhrononium, Tronomenhrononium
Vamidothion, XMC, Xylylcarb, YI 5301 / 5302, Zetamethrin.Vamidothione, XMC, xylylcarb, YI 5301/5302, zetamethrin.
Auch eine Mischung mit anderen bekannten Wirkstoffen, wie Herbiziden oder mit Düngemitteln und Wachstumsregulatoren ist möglich.A mixture with other known active ingredients, such as herbicides or with fertilizers and growth regulators, is also possible.
Die erfindungsgemäßen Wirkstoffe können ferner beim Einsatz als Insektizide in ihren handelsüblichen Formulierungen sowie in den aus diesen Formulierungen bereiteten Anwendungsformen in Mischung mit Synergisten vorliegen. Synergisten sind Verbindungen, durch die die Wirkung der Wirkstoffe gesteigert wird, ohne daß der zugesetzte Synergist selbst aktiv wirksam sein muß. Der Wirkstoffgehalt der aus den handelsüblichen Formulierungen bereiteten Anwendungsformen kann in weiten Bereichen variieren. Die Wirkstoffkonzentration der Anwendungsformen kann von 0,0000001 bis zu 95 Gew.-% Wirkstoff, vorzugsweise zwischen 0,0001 und 1 Gew.-% liegen.When used as insecticides, the active compounds according to the invention can also be present in their commercially available formulations and in the use forms prepared from these formulations in a mixture with synergists. Synergists are compounds through which the action of the active ingredients is increased without the added synergist itself having to be active. The active substance content of the use forms prepared from the commercially available formulations can vary within wide ranges. The active substance concentration of the use forms can be from 0.0000001 to 95% by weight of active substance, preferably between 0.0001 and 1% by weight.
Die Anwendung geschieht in einer den Anwendungsformen angepaßten üblichen Weise.The application takes place in a customary manner adapted to the application forms.
Bei der Anwendung gegen Hygiene- und Vorratsschädlinge zeichnet sich der Wirkstoff durch eine hervorragende Residualwirkung auf Holz und Ton sowie durch eine gute Alkalistabilität auf gekalkten Unterlagen aus.When used against hygiene pests and pests of stored products, the active ingredient is distinguished by an excellent residual action on wood and clay as well as a good stability to alkali on limed substrates.
Die erfindungsgemäßen Wirkstoffe wirken nicht nur gegen Pflanzen-, Hygiene- und Vorratsschädlinge, sondern auch auf dem veterinärmedizinischen Sektor gegen tierische Parasiten (Ektoparasiten) wie Schildzecken, Lederzecken, Räudemilben, Laufmilben, Fliegen (stechend und leckend), parasitierende Fliegenlarven, Läuse, Haarlinge, Federlinge und Flöhe. Zu diesen Parasiten gehören:The active compounds according to the invention act not only against plant, hygiene and stored-product pests, but also in the veterinary sector against animal parasites (ectoparasites) such as tick ticks, leather ticks, mites, running mites, flies (stinging and licking), parasitic fly larvae, lice, hair lice, Featherlings and fleas. These parasites include:
Aus der Ordnung der Anoplurida z.B. Haematopinus spp., Linognathus spp.,From the order of the Anoplurida e.g. Haematopinus spp., Linognathus spp.,
Pediculus spp., Phtirus spp., Solenopotes spp..Pediculus spp., Phtirus spp., Solenopotes spp ..
Aus der Ordnung der Mallophagida und den Unterordnungen Amblycerina sowieFrom the order of the Mallophagida and the subordinates Amblycerina as well
Ischnocerina z.B. Trimenopon spp., Menopon spp., Trinoton spp., Bovicola spp., Werneckiella spp., Lepikentron spp., Damalina spp., Trichodectes spp., Felicola spp..Ischnocerina e.g. Trimenopon spp., Menopon spp., Trinoton spp., Bovicola spp., Werneckiella spp., Lepikentron spp., Damalina spp., Trichodectes spp., Felicola spp ..
Aus der Ordnung Diptera und den Unterordnungen Nematocerina sowie Brachycerina z.B. Aedes spp., Anopheles spp., Culex spp., Simulium spp., Eusimulium spp., Phlebotomus spp., Lutzomyia spp., Culicoides spp., Chrysops spp., Hybomitra spp., Atylotus spp., Tabanus spp., Haematopota spp., Philipomyia spp.,From the order Diptera and the subordinates Nematocerina and Brachycerina e.g. Aedes spp., Anopheles spp., Culex spp., Simulium spp., Eusimulium spp., Phlebotomus spp., Lutzomyia spp., Culicoides spp., Chrysops spp., Hybomitra spp., Atylotus spp., Tabanus spp., Haematopota ., Philipomyia spp.,
Braula spp., Musca spp., Hydrotaea spp., Stomoxys spp., Haematobia spp., Morellia spp., Fannia spp., Glossina spp., Calliphora spp., Lucilia spp., Chrysomyia spp.,- Wohlfahrtia spp., Sarcophaga spp., Oestrus spp., Hypoderma spp., Gasterophilus spp., Hippobosca spp., Lipoptena spp., Melophagus spp..Braula spp., Musca spp., Hydrotaea spp., Stomoxys spp., Haematobia spp., Morellia spp., Fannia spp., Glossina spp., Calliphora spp., Lucilia spp., Chrysomyia spp., - Wohlfahrtia spp., Sarcophaga spp., Oestrus spp., Hypoderma spp., Gasterophilus spp., Hippobosca spp., Lipoptena spp ., Melophagus spp ..
Aus der Ordnung der Siphonapterida z.B. Pulex spp., Ctenocephalides spp.,From the order of the Siphonapterida e.g. Pulex spp., Ctenocephalides spp.,
Xenopsylla spp., Ceratophyllus spp..Xenopsylla spp., Ceratophyllus spp ..
Aus der Ordnung der Heteropterida z.B. Cimex spp., Triatoma spp., Rhodnius spp., Panstrongylus spp..From the order of the Heteropterida e.g. Cimex spp., Triatoma spp., Rhodnius spp., Panstrongylus spp ..
Aus der Ordnung der Blattarida z.B. Blatta orientalis, Periplaneta americana, Blattela germanica, Supella spp..From the order of the Blattarida e.g. Blatta orientalis, Periplaneta americana, Blattela germanica, Supella spp ..
Aus der Unterklasse der Acaria (Acarida) und den Ordnungen der Meta- sowie Mesostigmata z.B. Argas spp., Ornithodorus spp., Otobius spp., Ixodes spp.,From the subclass of Acaria (Acarida) and the orders of the Meta and Mesostigmata e.g. Argas spp., Ornithodorus spp., Otobius spp., Ixodes spp.,
Amblyomma spp., Boophilus spp., Dermacentor spp., Haemophysalis spp., Hyalomma spp., Rhipicephalus spp., Dermanyssus spp., Raillietia spp., Pneumonyssus spp., Sternostoma spp., Varroa spp..Amblyomma spp., Boophilus spp., Dermacentor spp., Haemophysalis spp., Hyalomma spp., Rhipicephalus spp., Dermanyssus spp., Raillietia spp., Pneumonyssus spp., Sternostoma spp., Varroa spp ..
Aus der Ordnung der Actinedida (Prostigmata) und Acaridida (Astigmata) z.B.From the order of the Actinedida (Prostigmata) and Acaridida (Astigmata) e.g.
Acarapis spp., Cheyletiella spp., Ornithocheyletia spp., Myobia spp., Psorergates spp., Demodex spp., Trombicula spp., Listrophorus spp., Acarus spp., Tyrophagus spp., Caloglyphus spp., Hypodectes spp., Pterolichus spp., Psoroptes spp., Chorioptes spp., Otodectes spp., Sarcoptes spp., Notoedres spp., Knemidocoptes spp., Cytodites spp., Laminosioptes spp..Acarapis spp., Cheyletiella spp., Ornithocheyletia spp., Myobia spp., Psorergates spp., Demodex spp., Trombicula spp., Listrophorus spp., Acarus spp., Tyrophagus spp., Caloglyphus spp., Hypodterol spp ., Psoroptes spp., Chorioptes spp., Otodectes spp., Sarcoptes spp., Notoedres spp., Knemidocoptes spp., Cytodites spp., Laminosioptes spp ..
Beispielsweise zeigen sie eine gute Wirksamkeit gegen Fliegen (Musca domestica), entwicklungshemmende Wirkung gegen Fliegenlarven von Lucilia cuprina sowie eine gute Wirkung gegen Katzenflöhe (Ctenocephalides felis) und gegen Zecken (Boophilus microplus), auch in Form einer Hemmung der Eiablage. Die erfindungsgemäßen Wirkstoffe der Formel (I) eignen sich auch zur Bekämpfung - von Arthropoden, die landwirtschaftliche Nutztiere, wie z.B. Rinder, Schafe, Ziegen, Pferde, Schweine, Esel, Kamele, Büffel, Kaninchen, Hühner, Puten. Enten, Gänse, Bienen, sonstige Haustiere wie z.B. Hunde, Katzen, Stubenvögel, Aquarienfische sowie sogenannte Versuchstiere, wie z.B. Hamster, Meerschweinchen, Ratten und Mäuse befallen. Durch die Bekämpfung dieser Arthropoden sollen Todesfälle und Leistungsminderungen (bei Fleisch, Milch, Wolle, Häuten, Eiern, Honig usw.) vermindert werden, so daß durch den Einsatz der erfindungsgemäßen Wirkstoffe eine wirtschaftlichere und einfachere Tierhaltung möglich ist.For example, they show good effectiveness against flies (Musca domestica), development-inhibiting effects against fly larvae of Lucilia cuprina, and good effects against cat fleas (Ctenocephalides felis) and ticks (Boophilus microplus), also in the form of an inhibition of egg laying. The active compounds of the formula (I) according to the invention are also suitable for combating arthropods which are agricultural animals such as cattle, sheep, goats, horses, pigs, donkeys, camels, buffalo, rabbits, chickens, turkeys. Ducks, geese, bees, other domestic animals such as dogs, cats, house birds, aquarium fish and so-called experimental animals such as hamsters, guinea pigs, rats and mice. By combating these arthropods, deaths and reduced performance (in the case of meat, milk, wool, skins, eggs, honey, etc.) are to be reduced, so that the use of the active compounds according to the invention enables more economical and simple animal husbandry.
Die Anwendung der erfindungsgemäßen Wirkstoffe geschieht im Veterinärsektor in bekannter Weise durch enterale Verabreichung in Form von beispielsweise Tabletten, Kapseln, Tränken, Drenchen, Granulaten, Pasten, Boli, des feed-through-Verfahrens, von Zäpfchen, durch parenterale Verabreichung, wie zum Beispiel durch Injektionen (intramuskulär, subcutan, intravenös, intraperitonal u.a.), Implantate, durch nasaleThe active compounds according to the invention are used in the veterinary sector in a known manner by enteral administration in the form of, for example, tablets, capsules, drinkers, drenches, granules, pastes, boluses, the feed-through method, suppositories, by parenteral administration, for example by Injections (intramuscular, subcutaneous, intravenous, intraperitoneal, etc.), implants, through nasal
Applikation, durch dermale Anwendung in Form beispielsweise des Tauchens oder Badens (Dippen), Sprühens (Spray), Aufgießens (Pour-on und Spot-on), des Waschens, des Einpuderns sowie mit Hilfe von wirkstoffhaltigen Formkörpern, wie Halsbändern, Ohrmarken, Schwanzmarken, Gliedmaßenbändern, Halftern, Markie- rungsvorrichtungen usw.Application, by dermal application in the form of, for example, diving or bathing (dipping), spraying (spray), pouring on (pour-on and spot-on), washing, powdering and with the help of shaped articles containing active ingredients, such as collars, ear tags, tail tags , Limb straps, holsters, marking devices etc.
Bei der Anwendung für Vieh, Geflügel, Haustiere etc. kann man die Wirkstoffe der Formel (I) als Formulierungen (beispielsweise Pulver, Emulsionen, fließfähige Mittel), die die Wirkstoffe in einer Menge von 1 bis 80 Gew.-% enthalten, direkt oder nach 100 bis 10 000-facher Verdünnung anwenden oder sie als chemisches Bad verwenden.When used for cattle, poultry, pets, etc., the active compounds of the formula (I) can be used as formulations (for example powders, emulsions, flowable agents) which contain the active compounds in an amount of 1 to 80% by weight, directly or apply after 100 to 10,000-fold dilution or use it as a chemical bath.
Außerdem wurde gefunden, daß die erfindungsgemäßen Verbindungen der Formel (I) eine hohe insektizide Wirkung gegen Insekten zeigen, die technische Materialien zerstören. Beispielhaft und vorzugsweise - ohne jedoch zu limitieren - seien die folgenden- Insekten genannt:It has also been found that the compounds of the formula (I) according to the invention have a high insecticidal action against insects which destroy industrial materials. The following insects may be mentioned by way of example and preferably, but without limitation:
Käfer wie Hylotrupes bajulus, Chlorophorus pilosis, Anobium punctatum, Xestobium rufovillosum, Ptilinus pecticomis, Dendrobium pertinex, Ernobius mollis, Priobium caφini, Lyctus brunneus, Lyctus africanus, Lyctus planicollis, Lyctus linearis, Lyctus pubescens, Trogoxylon aequale, Minthes rugicollis; Xyleborus spec. Tryptodendron spec. Apate monachus, Bostrychus capucins, Heterobostrychus brunneus, Sinoxylon spec. Dinoderus minutusBeetles such as Hylotrupes bajulus, Chlorophorus pilosis, Anobium punctatum, Xestobium rufovillosum, Ptilinus pecticomis, Dendrobium pertinex, Ernobius mollis, Priobium caφini, Lyctus brunneus, Lyctus africanus, Lyctus planicescisis, Lyctus pubcollis, Lyctus pubcollis, Lyctus pubicollis, Lyctus pubxollis, Lyctus pubis Xyleborus spec. Tryptodendron spec. Apate monachus, Bostrychus capucins, Heterobostrychus brunneus, Sinoxylon spec. Dinoderus minutus
Hautflügler wieSkin wings like
Sirex juvencus, Urocerus gigas, Urocerus gigas taignus, Urocerus augurSirex juvencus, Urocerus gigas, Urocerus gigas taignus, Urocerus augur
Termiten wieTermites like
Kalotermes flavicollis, Cryptotermes brevis, Heterotermes indicola, Reticulitermes flavipes, Reticulitermes santonensis, Reticulitermes lucifugus, Mastotermes darwiniensis, Zootermopsis nevadensis, Coptotermes formosanus.Kalotermes flavicollis, Cryptotermes brevis, Heterotermes indicola, Reticulitermes flavipes, Reticulitermes santonensis, Reticulitermes lucifugus, Mastotermes darwiniensis, Zootermopsis nevadensis, Coptotermes formosanus.
Borstenschwänze, wie Lepisma saccarina.Bristle tails, such as Lepisma saccarina.
Unter technischen Materialien sind im vorliegenden Zusammenhang nicht-lebende Materialien zu verstehen, wie vorzugsweise Kunststoffe, Klebstoffe, Leime, Papiere und Kartone, Leder, Holz und Holzverarbeitungsprodukte und Anstrichmittel.In the present context, technical materials are understood to mean non-living materials, such as preferably plastics, adhesives, glues, papers and cartons, leather, wood and wood processing products and paints.
Ganz besonders bevorzugt handelt es sich bei dem vor Insektenbefall zu schützenden Material um Holz und Holzverarbeitungsprodukte.The material to be protected against insect infestation is very particularly preferably wood and wood processing products.
Unter Holz und Holzverarbeitungsprodukten, welche durch das erfindungsgemäße Mittel bzw. dieses enthaltende Mischungen geschützt werden kann, ist beispielhaft zu verstehen: Bauholz, Holzbalken, Eisenbahnschwellen, Brückenteile, Bootsstege, Holzfahrzeuge, Kisten, Paletten, Container, Telefonmasten, Holzverkleidungen, - Holzfenster und- türen, Sperrholz, Spanplatten, Tischlerarbeiten oder Holzprodukte, die ganz allgemein beim Hausbau oder in der Bautischlerei Verwendung finden.Wood and wood processing products which can be protected by the agent according to the invention or mixtures containing it are to be understood as examples: timber, wooden beams, railway sleepers, bridge parts, boat jetties, Wooden vehicles, boxes, pallets, containers, telephone poles, wooden cladding, wooden windows and doors, plywood, chipboard, carpentry or wooden products that are used in general in house construction or joinery.
Die Wirkstoffe können als solche, in Form von Konzentraten oder allgemein üblichen Formuliemngen wie Pulver, Granulate, Lösungen, Suspensionen, Emulsionen oder Pasten angewendet werden.The active compounds can be used as such, in the form of concentrates or generally customary formulations, such as powders, granules, solutions, suspensions, emulsions or pastes.
Die genannten Formuliemngen können in an sich bekannter Weise hergestellt wer- den, z.B. durch Vermischen der Wirkstoffe mit mindestens einem Lösungs- bzw.The formulations mentioned can be prepared in a manner known per se, e.g. by mixing the active ingredients with at least one solution or
Verdünnungsmittel, Emulgator, Dispergier- und/oder Binde- oder Fixiermittels, Wasser-Repellent, gegebenenfalls Sikkative und UV-Stabilisatoren und gegebenenfalls Farbstoffen und Pigmenten sowie weiteren Verarbeitungshilfsmitteln.Diluent, emulsifier, dispersant and / or binder or fixative, water repellent, optionally siccatives and UV stabilizers and optionally dyes and pigments and other processing aids.
Die zum Schutz von Holz und Holzwerkstoffen verwendeten insektiziden Mittel oderThe insecticidal agents or used to protect wood and wood-based materials
Konzentrate enthalten den erfindungsgemäßen Wirkstoff in einer Konzentration von 0,0001 bis 95 Gew.-%, insbesondere 0,001 bis 60 Gew.-%.Concentrates contain the active ingredient according to the invention in a concentration of 0.0001 to 95% by weight, in particular 0.001 to 60% by weight.
Die Menge der eingesetzten Mittel bzw. Konzentrate ist von der Art und dem Vor- kommen der Insekten und von dem Medium abhängig. Die optimale Einsatzmenge kann bei der Anwendung jeweils durch Testreihen ermittelt werden. Im allgemeinen ist es jedoch ausreichend 0,0001 bis 20 Gew.-%, vorzugsweise 0,001 bis 10 Gew.-%, des Wirkstoffs, bezogen auf das zu schützende Material, einzusetzen.The amount of the agents or concentrates used depends on the type and occurrence of the insects and on the medium. The optimal amount can be determined in each case by test series. In general, however, it is sufficient to use 0.0001 to 20% by weight, preferably 0.001 to 10% by weight, of the active compound, based on the material to be protected.
Als Lösungs- und/oder Verdünnungsmittel dient ein organisch-chemisches Lösungsmittel oder Lösungsmittelgemisch und/oder ein öliges oder ölartiges schwer flüchtiges organisch-chemisches Lösungsmittel oder Lösungsmittelgemisch und/oder ein polares organisch-chemisches Lösungsmittel oder Lösungsmittelgemisch und/oder Wasser und gegebenenfalls einen Emulgator und/oder Netzmittel. Als organisch-chemische Lösungsmittel werden vorzugsweise ölige oder ölartige - Lösungsmittel mit einer Verdunstungszahl über 35 und einem Flammpunkt oberhalb 30°C, vorzugsweise oberhalb 45°C, eingesetzt. Als derartige schwerflüchtige, wasserunlösliche, ölige und ölartige Lösungsmittel werden entsprechende Mineralöle oder deren Aromatenfraktionen oder mineralölhaltige Lösungsmittelgemische, vorzugsweise Testbenzin, Petroleum und/oder Alkylbenzol verwendet.An organic-chemical solvent or solvent mixture and / or an oily or oily or low-volatility organic-chemical solvent or solvent mixture and / or a polar organic-chemical solvent or solvent mixture and / or water and optionally an emulsifier and / or wetting agents. The organic chemical solvents used are preferably oily or oily solvents with an evaporation number above 35 and a flash point above 30 ° C., preferably above 45 ° C. Corresponding mineral oils or their aromatic fractions or mineral oil-containing solvent mixtures, preferably white spirit, petroleum and / or alkylbenzene, are used as such low-volatility, water-insoluble, oily and oily solvents.
Vorteilhaft gelangen Mineralöle mit einem Siedebereich von 170 bis 220°C, Testbenzin mit einem Siedebereich von 170 bis 220°C, Spindelöl mit einem Siedebereich von 250 bis 350°C, Petroleum bzw. Aromaten vom Siedebereich von 160 bis 280°C,Mineral oils with a boiling range of 170 to 220 ° C, white spirit with a boiling range of 170 to 220 ° C, spindle oil with a boiling range of 250 to 350 ° C, petroleum or aromatics with a boiling range of 160 to 280 ° C are advantageous.
Teφentinöl und dgl. zum Einsatz.Teφentinöl and the like. For use.
In einer bevorzugten Ausführungsform werden flüssige aliphatische Kohlenwasserstoffe mit einem Siedebereich von 180 bis 210°C oder hochsiedende Gemische von aromatischen und aliphatischen Kohlenwasserstoffen mit einem Siedebereich vonIn a preferred embodiment, liquid aliphatic hydrocarbons with a boiling range of 180 to 210 ° C or high-boiling mixtures of aromatic and aliphatic hydrocarbons with a boiling range of
180 bis 220°C und/oder Spindeöl und/oder Monochlornaphthalin, vorzugsweise α- Monochlornaphthalin, verwendet.180 to 220 ° C and / or locker oil and / or monochloronaphthalene, preferably α-monochloronaphthalene used.
Die organischen schwerflüchtigen öligen oder ölartigen Lösungsmittel mit einer Ver- dunstungszahl über 35 und einem Flammpunkt oberhalb 30°C, vorzugsweise oberhalb 45 °C, können teilweise durch leicht oder mittelflüchtige organisch-chemische Lösungsmittel ersetzt werden, mit der Maßgabe, daß das Lösungsmittelgemisch ebenfalls eine Verdunstungszahl über 35 und einen Flammpunkt oberhalb 30°C, vorzugsweise oberhalb 45 °C, aufweist und daß das Insektizid-Fungizid-Gemisch in diesem Lösungsmittelgemisch löslich oder emulgierbar ist.The organic low-volatility oily or oily solvents with an evaporation number above 35 and a flash point above 30 ° C., preferably above 45 ° C., can be partially replaced by slightly or medium-volatile organic chemical solvents, with the proviso that the solvent mixture is also a Evaporation number above 35 and a flash point above 30 ° C, preferably above 45 ° C, and that the insecticide-fungicide mixture is soluble or emulsifiable in this solvent mixture.
Nach einer bevorzugten Ausführungsform wird ein Teil des organisch-chemischen Lösungsmittel oder Lösungsmittelgemisches oder ein aliphatisches polares organisch-chemisches Lösungsmittel oder Lösungsmittelgemisch ersetzt. Vorzugsweise gelangen Hydroxyl- und/oder Ester- und/oder Ethergruppen enthaltende aliphatische organisch-chemische Lösungsmittel wie beispielsweise Glycolether, Ester oder dgl.- zur Anwendung.According to a preferred embodiment, part of the organic chemical solvent or solvent mixture or an aliphatic polar organic chemical solvent or solvent mixture is replaced. Aliphatic hydroxyl and / or ester and / or ether groups are preferably used organic chemical solvents such as glycol ether, ester or the like - for use.
Als organisch-chemische Bindemittel werden im Rahmen der vorliegenden Erfin- düng die an sich bekannten wasserverdünnbaren und/oder in den eingesetzten organisch-chemischen Lösungsmitteln löslichen oder dispergier- bzw. emulgierbaren Kunstharze und/oder bindende trocknende Öle, insbesondere Bindemittel bestehend aus oder enthaltend ein Acrylatharz, ein Vinylharz, z.B. Polyvinylacetat, Polyesterharz, Polykondensations- oder Polyadditionsharz, Polyurethanharz, Alkydharz bzw. modifiziertes Alkydharz, Phenolharz, Kohlenwasserstoffharz wie Inden-Cumaron- harz, Siliconharz, trocknende pflanzliche und/oder trocknende Öle und/oder physikalisch trocknende Bindemittel auf der Basis eines Natur- und/oder Kunstharzes verwendet.In the context of the present invention, the known water-thinnable synthetic resins and / or synthetic resins which are soluble or dispersible or emulsifiable in the organic chemical solvents used and / or binding drying oils, in particular binders consisting of or containing, are used as organic chemical binders Acrylate resin, a vinyl resin, e.g. Polyvinyl acetate, polyester resin, polycondensation or polyaddition resin, polyurethane resin, alkyd resin or modified alkyd resin, phenolic resin, hydrocarbon resin such as indene-coumarone resin, silicone resin, drying vegetable and / or drying oils and / or physically drying binders based on a natural and / / or synthetic resin used.
Das als Bindemittel verwendete Kunstharz kann in Form einer Emulsion, Dispersion oder Lösung, eingesetzt werden. Als Bindemittel können auch Bitumen oder bituminöse Substanzen bis zu 10 Gew.-%, verwendet werden. Zusätzlich können an sich bekannte Farbstoffe, Pigmente, wasserabweisende Mittel, Geruchskorrigentien und Inhibitoren bzw. Korrosionsschutzmittel und dgl. eingesetzt werden.The synthetic resin used as a binder can be used in the form of an emulsion, dispersion or solution. Bitumen or bituminous substances up to 10% by weight can also be used as binders. In addition, known dyes, pigments, water-repellants, odor correctors and inhibitors or anticorrosive agents and the like can be used.
Bevorzugt ist gemäß der Erfindung als organisch-chemische Bindemittel mindestens ein Alkydharz bzw. modifiziertes Alkydharz und/oder ein trocknendes pflanzliches Öl im Mittel oder im Konzentrat enthalten. Bevorzugt werden gemäß der Erfindung Alkydharze mit einem Ölgehalt von mehr als 45 Gew.-%, vorzugsweise 50 bis 68 Gew.-%, verwendet.According to the invention, at least one alkyd resin or modified alkyd resin and / or a drying vegetable oil is preferably contained in the agent or in the concentrate as the organic chemical binder. Alkyd resins with an oil content of more than 45% by weight, preferably 50 to 68% by weight, are preferably used according to the invention.
Das erwähnte Bindemittel kann ganz oder teilweise durch ein Fixierungsmit- tel(gemisch) oder ein Weichmacher(gemisch) ersetzt werden. Diese Zusätze sollen einer Verflüchtigung der Wirkstoffe sowie einer Kristallisation bzw. Ausfällem vor- beugen. Vorzugsweise ersetzen sie 0,01 bis 30 % des Bindemittels (bezogen aufAll or part of the binder mentioned can be replaced by a fixative (mixture) or a plasticizer (mixture). These additives are intended to prevent volatilization of the active ingredients and crystallization or precipitation. They preferably replace 0.01 to 30% of the binder (based on
100 % des eingesetzten Bindemittels). Die Weichmacher stammen aus den chemischen Klassen der Phthalsäureester wie Dibutyl-, Dioctyl- oder Benzylbutylphthalat, Phosphorsäureester wie Tributylphos- phat, Adipinsäureester wie Di-(2-ethylhexyl)-adipat, Stearate wie Butylstearat oder Amylstearat, Oleate wie Butyloleat, Glycerinether oder höhermolekulare Glykol- ether, Glycerinester sowie p-Toluolsulfonsäureester.100% of the binder used). The plasticizers come from the chemical classes of phthalic acid esters such as dibutyl, dioctyl or benzyl butyl phthalate, phosphoric acid esters such as tributyl phosphate, adipic acid esters such as di- (2-ethylhexyl) adipate, stearates such as butyl stearate or amyl stearate, oleates such as butyl oleate or higher molecular glycerol ether, glycerol ether, glycerol ether, glycerol ether, glycerol ether, glycerol ether, glycerol ether, glycerol ether, glycerol ether - ether, glycerol ester and p-toluenesulfonic acid ester.
Fixierungsmittel basieren chemisch auf Polyvinylalkylethern wie z.B. Polyvinylme- thylether oder Ketonen wie Benzophenon, Ethylenbenzophenon.Fixing agents are chemically based on polyvinyl alkyl ethers such as e.g. Polyvinyl methyl ether or ketones such as benzophenone, ethylene benzophenone.
Als Lösungs- bzw. Verdünnungsmittel kommt insbesondere auch Wasser in Frage, gegebenenfalls in Mischung mit einem oder mehreren der oben genannten organischchemischen Lösungs- bzw. Verdünnungsmittel, Emulgatoren und Dispergatoren.Water is also particularly suitable as a solvent or diluent, if appropriate in a mixture with one or more of the above-mentioned organic chemical solvents or diluents, emulsifiers and dispersants.
Ein besonders effektiver Holzschutz wird durch großtechnische Imprägnierverfahren, z.B. Vakuum. Doppelvakuum oder Druckverfahren, erzielt.A particularly effective wood protection is achieved through industrial impregnation processes, e.g. Vacuum. Double vacuum or printing process.
Die anwendungsfertigen Mittel können gegebenenfalls noch weitere Insektizide und gegebenenfalls noch ein oder mehrere Fungizide enthalten.The ready-to-use compositions can optionally contain further insecticides and, if appropriate, one or more fungicides.
Als zusätzliche Zumischpartner kommen vorzugsweise die in der Wo 94/29 268 genannten Insektizide und Fungizide in Frage. Die in diesem Dokument genannten Verbindungen sind ausdrücklicher Bestandteil der vorliegenden Anmeldung.The insecticides and fungicides mentioned in Wo 94/29 268 are particularly suitable as additional mixing partners. The compounds mentioned in this document are an integral part of the present application.
Als ganz besonders bevorzugte Zumischpartner können Insektizide, wie Chlorpyri- phos, Phoxim, Silafluofin, Alphamethrin, Cyfluthrin, Cypermethrin, Deltamethrin, Permethrin, Imidacloprid, NI-25, Flufenoxuron, Hexaflumuron und Triflumuron. sowie Fungizide wie Epoxyconazole, Hexaconazole, Azaconazole, Propiconazole, Tebuconazole, Cyproconazole, Metconazole, Imazalil, Dichlorfluanid. Tolylfluanid, 3-Iod-2-propinyl-butylcarbamat, N-Octyl-isothiazolin-3-on und 4,5-Dichlor-N- octylisothiazolin-3-on, sein. Die Herstellung und die Verwendung der erfindungsgemäßen Wirkstoffe gehen aus den nachfolgenden Beispielen hervor. Insecticides such as chlorpyriphos, phoxime, silafluofin, alphamethrin, cyfluthrin, cypermethrin, deltamethrin, permethrin, imidacloprid, NI-25, flufenoxuron, hexaflumuron and triflumuron can be used as very particularly preferred mixing partners. as well as fungicides such as epoxyconazole, hexaconazole, azaconazole, propiconazole, tebuconazole, cyproconazole, metconazole, imazalil, dichlorfluanide. Tolylfluanid, 3-iodo-2-propynyl butyl carbamate, N-octyl-isothiazolin-3-one and 4,5-dichloro-N-octylisothiazolin-3-one. The preparation and use of the active compounds according to the invention can be seen from the examples below.
HerstellungsbeispieleManufacturing examples
Beispiel 1example 1
0,8 g (2,1 mMol) 5-Amino-3-cyano-4-ethylthio-l-(2,6-dichlor-4-trifluormethylphe- nyl)-pyrazol (vgl. EP 295 117) werden in 30 ml wasserfreiem Pyridin und 2 ml Triethylamin gelöst. Bei Raumtemperatur wird langsam Schwefelwasserstoff eingeleitet, wobei die Temperatur auf 28°C ansteigt. Nach 60 Minuten ist die Umsetzung beendet. Das Reaktionsgemisch wird eingeengt und das Rohprodukt chromatographisch an Kieselgel (Cyclohexan/Essigsäureethylester: 2/1) gereinigt.0.8 g (2.1 mmol) of 5-amino-3-cyano-4-ethylthio-1- (2,6-dichloro-4-trifluoromethylphenyl) pyrazole (cf. EP 295 117) are dissolved in 30 ml anhydrous pyridine and 2 ml of triethylamine dissolved. At room temperature, hydrogen sulfide is slowly introduced, the temperature rising to 28 ° C. The reaction is complete after 60 minutes. The reaction mixture is concentrated and the crude product is purified by chromatography on silica gel (cyclohexane / ethyl acetate: 2/1).
Man erhält 0,4 g (46% der Theorie) 5-Amino-4-ethylthio-l-(2,6-dichlor-4-trifluor- methylphenyl)-3-thiocarbamoyl-pyrazol vom Schmelzpunkt 101°C.0.4 g (46% of theory) of 5-amino-4-ethylthio-1- (2,6-dichloro-4-trifluoromethylphenyl) -3-thiocarbamoyl-pyrazole of melting point 101 ° C. is obtained.
Analog Beispiel 1 bzw. gemäß den allgemeinen Angaben zur Herstellung werden die in der folgenden Tabelle A angegebenen Verbindungen der Formel (I) erhalten: Tabelle AThe compounds of the formula (I) given in Table A below are obtained analogously to Example 1 or according to the general information on the preparation: Table A
AnwendungsbeispieleExamples of use
Beispiel AExample A
Myzus-TestMyzus test
Lösungsmittel: 7 Gewichtsteile Dimethylformamid Emulgator: 1 Gewichtsteil AlkylarylpolyglykoletherSolvent: 7 parts by weight of dimethylformamide emulsifier: 1 part by weight of alkylaryl polyglycol ether
Zur Herstellung einer zweckmäßigen Wirkstoffzubereitung vermischt man 1 Gewichtsteil Wirkstoff mit den angegebenen Mengen Lösungsmittel und Emulgator und verdünnt das Konzentrat mit Wasser auf die gewünschte Konzentration.To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration.
Kohlblätter (Brassica oleracea), die stark von der Pfirsichblattlaus (Mycus persicae) befallen sind, werden durch Tauchen in die Wirkstoffzubereitung der gewünschtenCabbage leaves (Brassica oleracea), which are heavily infested with the peach aphid (Mycus persicae), are dipped into the active ingredient preparation of the desired
Konzentration behandelt.Concentration treated.
Nach der gewünschten Zeit wird die Abtötung in % bestimmt. Dabei bedeutet 100 %, daß alle Blattläuse abgetötet wurden; 0 % bedeutet, daß keine Blattläuse abgetötet wurden.After the desired time, the kill is determined in%. 100% means that all aphids have been killed; 0% means that no aphids have been killed.
In diesem Test zeigte bei einer beispielhaften Wirkstoffkonzentration von 0,1 % z.B. die Verbindung des Herstellungsbeispiels 1 eine Abtötung von 90 % und die Verbindungen der Herstellungsbeispiele 2 und 8 eine Abtötung von 100 %, jeweils nach 6 Tagen. Beispiel BIn this test, at an exemplary active ingredient concentration of 0.1%, for example the compound of preparation example 1 showed a kill of 90% and the compounds of preparation examples 2 and 8 showed a kill of 100%, in each case after 6 days. Example B
Spodoptera frugiperda-TestSpodoptera frugiperda test
Lösungsmittel: 7 Gewichtsteile DimethylformamidSolvent: 7 parts by weight of dimethylformamide
Emulgator: 1 Gewichtsteil AlkylarylpolyglykoletherEmulsifier: 1 part by weight of alkylaryl polyglycol ether
Zur Herstellung einer zweckmäßigen Wirkstoffzubereitung vermischt man 1 Gewichtsteil Wirkstoff mit der angegebenen Menge Lösungsmittel und der angege- benen Menge Emulgator und verdünnt das Konzentrat mit Wasser auf die gewünschte Konzentration.To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amount of solvent and the given amount of emulsifier, and the concentrate is diluted with water to the desired concentration.
Kohlblätter (Brassica oleracea) werden durch Tauchen in die Wirkstoffzubereitung der gewünschten Konzentration behandelt und mit Raupen des Heerwurms (Spodoptera frugiperda) besetzt, solange die Blätter noch feucht sind.Cabbage leaves (Brassica oleracea) are treated by being dipped into the preparation of active compound of the desired concentration and populated with caterpillars of the army worm (Spodoptera frugiperda) while the leaves are still moist.
Nach der gewünschten Zeit wird die Abtötung in % bestimmt. Dabei bedeutet 100 %, daß alle Raupen abgetötet wurden; 0 % bedeutet, daß keine Raupen abgetötet wurden.After the desired time, the kill is determined in%. 100% means that all caterpillars have been killed; 0% means that no caterpillars have been killed.
In diesem Test zeigte z.B. die Verbindung des Herstellungsbeispiels 2 bei einer beispielhaften Wirkstoffkonzentration von 0,1 % eine Abtötung von 85 % nach 7 Tagen. In this test, for example, the compound of preparation example 2, with an exemplary active compound concentration of 0.1%, showed a kill of 85% after 7 days.
Beispiel CExample C
Test mit Fliegen (Musca domestica)Test with flies (Musca domestica)
Testtiere: adulte Musca domestica, Stamm Reichswald (OP, SP, Carbamat- resistent) Lösungsmittel: DimethylsulfoxidTest animals: adult Musca domestica, strain Reichswald (OP, SP, carbamate-resistant) solvent: dimethyl sulfoxide
20 mg Wirkstoff werden in 1 ml Dimethylsulfoxid gelöst, geringere Konzentrationen werden durch Verdünnen mit Dest H2O hergestellt.20 mg of active ingredient are dissolved in 1 ml of dimethyl sulfoxide, lower concentrations are produced by dilution with Dest H 2 O.
2 ml dieser Wirkstoffzubereitung werden auf Filteφapierschalen (0 9,5 cm) pipet- tiert, die sich in Petrischalen entsprechender Größe befinden. Nach Trocknung der Filterscheiben werden 25 Testtiere in die Petrischalen überführt und abgedeckt.2 ml of this active ingredient preparation are pipetted onto filter paper dishes (0 9.5 cm), which are located in Petri dishes of the appropriate size. After the filter discs have dried, 25 test animals are transferred to the Petri dishes and covered.
Nach 1, 3, 5, 24 und 48 Stunden wird die Wirksamkeit der Wirkstoffzubereitung ermittelt. Dabei bedeutet 100 %, daß alle Fliegen abgetötet wurden; 0 % bedeutet, daß keine Fliegen abgetötet wurden.After 1, 3, 5, 24 and 48 hours, the effectiveness of the active ingredient preparation is determined. 100% means that all flies have been killed; 0% means that no flies have been killed.
Bei diesem Test zeigte z.B. die Verbindung des Herstellungsbeispiels 2 bei einer beispielhaften Wirkstoffkonzentration von 100 ppm eine 100 %-ige Wirkung. In this test, for example, the compound of preparation example 2 showed a 100% action at an exemplary active ingredient concentration of 100 ppm.
Beispiel DExample D
Blo fly-Larven-Test / Entwicklungshemmende WirkungBlo fly larva test / development-inhibiting effect
Testtiere: Lucilia cuprina-LarvenTest animals: Lucilia cuprina larvae
Lösungsmittel: DimethylsulfoxidSolvent: dimethyl sulfoxide
20 mg Wirkstoff werden in 1 ml Dimethylsulfoxid gelöst, geringere Konzentrationen werden durch Verdünnen mit Dest H2O hergestellt.20 mg of active ingredient are dissolved in 1 ml of dimethyl sulfoxide, lower concentrations are produced by dilution with Dest H 2 O.
Etwa 20 Lucilia cuprina-Larven werden in ein Teströhrchen gebracht, welches ca. 1 cm3 Pferdefleisch und 0,5 ml der Wirkstoffzubereitung enthält. Nach 24 und 48 Stunden wird die Wirksamkeit der Wirkstoffzubereitung ermittelt. Die Teströhrchen werden in Becher mit Sand-bedecktem Boden überführt. Nach weiteren 2 Tagen wer- den die Teströhrchen entfernt und die Puppen ausgezählt.About 20 Lucilia cuprina larvae are placed in a test tube, which contains approx. 1 cm 3 horse meat and 0.5 ml of the active ingredient preparation. The effectiveness of the active substance preparation is determined after 24 and 48 hours. The test tubes are transferred to beakers with a sand-covered bottom. After a further 2 days, the test tubes are removed and the dolls are counted.
Die Wirkung der Wirkstoffzubereitung wird nach der Zahl der geschlüpften Fliegen nach 1,5-facher Entwicklungsdauer einer unbehandelten Kontrolle beurteilt. Dabei bedeutet 100 %, daß keine Fliegen geschlüpft sind; 0 % bedeutet, daß alle Fliegen normal geschlüpft sind.The effect of the preparation of active substance is assessed according to the number of flies hatched after 1.5 times the development time of an untreated control. 100% means that no flies have hatched; 0% means that all flies hatched normally.
Bei diesem Test zeigten z.B. die Verbindungen der Herstellungsbeispiele 1 und 2 bei einer beispielhaften Wirkstoffkonzentration von 100 ppm eine 100 %-ige Wirkung. In this test, the compounds of Preparation Examples 1 and 2, for example, showed a 100% action at an exemplary active ingredient concentration of 100 ppm.
Beispiel EExample E
Test mit Boophilus microplus resistent / SP-resistenter Parkhurst-StammTest with Boophilus microplus resistant / SP-resistant Parkhurst strain
Testtiere: adulte gesogene WeibchenTest animals: adult sucked females
Lösungsmittel: DimethylsulfoxidSolvent: dimethyl sulfoxide
20 mg Wirkstoff werden in 1 ml Dimethylsulfoxid gelöst, geringere Konzentrationen werden durch Verdünnen mit Dest H2O hergestellt.20 mg of active ingredient are dissolved in 1 ml of dimethyl sulfoxide, lower concentrations are produced by dilution with Dest H 2 O.
10 adulte Boophilus microplus res. werden in die zu testende Wirkstoffzubereitung 1 Minute getaucht. Nach Überführung in Plastikbecher und Aufbewahrung in einem klimatisierten Raum wird der Abtötungsgrad bestimmt.10 adult Boophilus microplus res. are immersed in the drug preparation to be tested for 1 minute. After being transferred to a plastic cup and stored in an air-conditioned room, the degree of killing is determined.
Dabei bedeutet 100 %, daß alle Zecken abgetötet wurden; 0 % bedeutet, daß keine100% means that all ticks have been killed; 0% means that none
Zecken abgetötet wurden.Ticks were killed.
Bei diesem Test zeigte z.B. die Verbindung des Herstellungsbeispiels 1 bei einer beispielhaften Wirkstoffkonzentration von 100 ppm eine 100 %-ige Wirkung. In this test, for example, the compound of preparation example 1 showed a 100% action at an exemplary active ingredient concentration of 100 ppm.
Beispiel FExample F
Test mit Boophilus microplus resistent / SP-resistenter Parkhurst-StammTest with Boophilus microplus resistant / SP-resistant Parkhurst strain
Testtiere: adulte gesogene WeibchenTest animals: adult sucked females
Lösungsmittel: DimethylsulfoxidSolvent: dimethyl sulfoxide
20 mg Wirkstoff werden in 1 ml Dimethylsulfoxid gelöst, geringere Konzentrationen werden durch Verdünnen in dem gleichen Lösungsmittel hergestellt.20 mg of active ingredient are dissolved in 1 ml of dimethyl sulfoxide, lower concentrations are prepared by dilution in the same solvent.
Der Test wird in 5-fach-Bestimmung durchgeführt, l μl der Lösungen wird in das Abdomen injiziert, die Tiere in Schalen überführt und in einem klimatisierten Raum aufbewahrt. Die Wirkungskontrolle erfolgt nach 7 Tagen auf Hemmung der Eiablage. Eine Wirkung von 100 % bedeutet, daß keine Zecke Eier gelegt hat.The test is carried out in 5-fold determination, 1 μl of the solutions is injected into the abdomen, the animals are transferred into dishes and stored in an air-conditioned room. The effectiveness check is carried out after 7 days on the inhibition of egg laying. An effect of 100% means that no tick has laid eggs.
Bei diesem Test zeigten z.B. die Verbindungen der Herstellungsbeispiele 1 und 2 bei einer beispielhaften Wirkstoffkonzentration von 20 μg/Tier eine 100 %-ige Wirkung. In this test, the compounds of Preparation Examples 1 and 2, for example, showed a 100% activity at an exemplary active ingredient concentration of 20 μg / animal.
Beispiel GExample G
Test mit Katzenflöhen / orale AufnahmeTest with cat fleas / oral intake
Testtiere: Adulte von Ctenocephalides felisTest animals: adults of Ctenocephalides felis
Lösungsmittel: Dimethylsulfoxid (DMSO)Solvent: dimethyl sulfoxide (DMSO)
Zwecks Herstellung einer geeigneten Formulierung wird aus 20 mg Wirkstoff mit 1 ml DMSO eine geeignete Wirkstofflösung hergestellt. 15 μl dieser Formuliemng werden zu 3 ml citriertem Rinderblut gegeben und verrührt.To produce a suitable formulation, a suitable active ingredient solution is prepared from 20 mg of active ingredient with 1 ml of DMSO. 15 μl of this formulation are added to 3 ml of citrated cattle blood and stirred.
10 nüchterne adulte Flöhe (Ctenocephalides felis, Stamm „Georgi") werden in eine Kammer (0 3,2 cm) eingesetzt, die oben und unten mit Gaze verschlossen ist. Auf die Kammer wird ein Metalizylinder gestellt, dessen Unterseite mit Parafilm verschlossen ist. Der Zylinder enthält 3 ml Blut- Wirkstoffformulierung, die von den10 fasting adult fleas (Ctenocephalides felis, "Georgi" strain) are placed in a chamber (3.2 cm) which is closed with gauze at the top and bottom. A metal cylinder is placed on the chamber, the underside of which is sealed with parafilm. The cylinder contains 3 ml of blood active ingredient formulation, which by the
Flöhen durch die Parafilmmembran aufgenommen werden kann. Während das Blut auf 37°C erwärmt wird, wird im Bereich der Flohkammern eine Temperatur von 25°C eingestellt. Kontrollen werden mit dem gleichen Volumen DMSO ohne Zusatz einer Verbindung vermischt. Es werden Dreifach-Bestimmungen durchgeführt.Fleas can be absorbed through the parafilm membrane. While the blood is being heated to 37 ° C, a temperature of 25 ° C is set in the area of the flea chambers. Controls are mixed with the same volume of DMSO without the addition of a compound. Triple determinations are carried out.
Nach 28 Stunden wird die Mortalität in % (= tote Flöhe) bestimmt.After 28 hours, the mortality is determined in% (= dead fleas).
Bei diesem Test zeigte z.B. die Verbindung des Herstellungsbeispiels 2 bei einer beispielhaften Wirkstoffkonzentration von 100 ppm eine 100 %-ige Wirkung. Beispiel HIn this test, for example, the compound of preparation example 2 showed a 100% action at an exemplary active ingredient concentration of 100 ppm. Example H
Phaedon-Larven-TestPhaedon larval test
Lösungsmittel: 7 Gewichtsteile DimethylformamidSolvent: 7 parts by weight of dimethylformamide
Emulgator: 1 Gewichtsteil AlkylarylpolyglykoletherEmulsifier: 1 part by weight of alkylaryl polyglycol ether
Zur Herstellung einer zweckmäßigen Wirkstoffzubereitung vermischt man 1 Gewichtsteil Wirkstoff mit der angegebenen Menge Lösungsmittel und Emulgator und verdünnt das Konzentrat mit emulgatorhaltigem Wasser auf die gewünschteTo produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amount of solvent and emulsifier and the concentrate is diluted to the desired amount with water containing emulsifier
Konzentration.Concentration.
Kohlblätter (Brassica oleracea) werden durch Tauchen in die Wirkstoffzubereitung der gewünschten Konzentration behandelt und mit Larven des Meerrettichkäfers (Phaedon cochleariae) besetzt, solange die Blätter noch feucht sind.Cabbage leaves (Brassica oleracea) are treated by being dipped into the preparation of active compound of the desired concentration and populated with larvae of the horseradish beetle (Phaedon cochleariae) while the leaves are still moist.
Nach der gewünschten Zeit wird die Abtötung in % bestimmt. Dabei bedeutet 100 %, daß alle Raupen abgetötet wurden; 0 % bedeutet, daß keine Raupen abgetötet wurden.After the desired time, the kill is determined in%. 100% means that all caterpillars have been killed; 0% means that no caterpillars have been killed.
In diesem Test zeigen z.B. die Verbindungen der Herstellungsbeispiele 1 bis 9 bei einer beispielhaften Wirkstoffkonzentration von 0,1 % eine Abtötung von 100 % nach 7 Tagen. In this test e.g. the compounds of Preparation Examples 1 to 9 at an exemplary active ingredient concentration of 0.1%, a kill of 100% after 7 days.

Claims

Patentansprücheclaims
1. Substituierte 3-Thiocarbamoylpyrazole der allgemeinen Formel (I)1. Substituted 3-thiocarbamoylpyrazoles of the general formula (I)
in welcherin which
R1 für H2N-CS- steht,R 1 stands for H 2 N-CS-,
m für die Zahlen 0 oder 1 steht,m represents the numbers 0 or 1,
n für die Zahlen 0, 1 oder 2 steht,n represents the numbers 0, 1 or 2,
R2 für Alkyl, Alkenyl, Alkinyl, Cyanalkyl, Thiocyanatoalkyl, Nitroalkyl,R 2 represents alkyl, alkenyl, alkynyl, cyanoalkyl, thiocyanatoalkyl, nitroalkyl,
Alkylthioalkyl, Alkylsulfinylalkyl, Alkylsulfonylalkyl, Halogenalkylthioalkyl, Halogenalkylsulfinylalkyl, Halogenalkylsulfonylalkyl, Alkenylthioalkyl, Alkenylsulfinylalkyl, Alkenylsulfonylalkyl, Alkinylthioalkyl, Alkinylsulfinylalkyl, Alkinylsulfonylalkyl, Alkoxy- carbonylalkyl, Halogenalkoxycarbonylalkyl, Alkoxycarbonyl, Alke- nyloxycarbonyl, Halogenalkoxycarbonyl, Alkylcarbonyl, Alkoxyalkyl, Halogenalkoxyalkyl, Alkoxyalkylthioalkyl, Alkoxyalkyl- sulfinylalkyl, Alkoxyalkylsulfonylalkyl, Halogenalkoxyalkylthioalkyl. Halogenalkoxyalkylsulfinylalkyl, Halogenalkoxyalkylsulfonylalkyl, Alkylaminoalkyl, Dialkylaminoalkyl, Trialkylsilylalkyl; jeweils gegebenenfalls substituiertes Cycloalkyl, Cycloalkenyl oder Cycloalkylalkyl; sowie für jeweils gegebenenfalls im Arylteil bzw. Heteroarylteil substituiertes Aryl, Heteroaryl, Arylalkyl, Heteroarylalkyl, Aryloxyalkyl, Arylthioalkyl, Arylsulfinylalkyl, Arylsulfonylalkyl, Arylalkyloxyal- kyl, Arylalkylthioalkyl, Arylalkylsulfmylalkyl oder Arylalkylsul- fonylalkyl steht,Alkylthioalkyl, alkylsulfinylalkyl, alkylsulfonylalkyl, haloalkylthioalkyl, haloalkylsulfinylalkyl, haloalkylsulfonylalkyl, alkenylthioalkyl, alkenylsulfinylalkyl, alkenylsulfonylalkyl, alkynylthioalkyl, alkynylsulfinylalkyl, alkynylsulfonylalkyl, alkoxycarbonylalkyl, haloalkoxycarbonyloxyoxyoxyoxyoxyoxyoxy Alkoxyalkylsulfonylalkyl, haloalkoxyalkylthioalkyl. Haloalkoxyalkylsulfinylalkyl, haloalkoxyalkylsulfonylalkyl, alkylaminoalkyl, dialkylaminoalkyl, trialkylsilylalkyl; each optionally substituted cycloalkyl, cycloalkenyl or cycloalkylalkyl; and for aryl, heteroaryl, arylalkyl, heteroarylalkyl, aryloxyalkyl, arylthioalkyl, arylsulfinylalkyl, arylsulfonylalkyl, arylalkyloxyalkyl, arylalkylthioalkyl, arylalkylsulfmylalkyl or arylalkylsulfonyl, arylalkylsulfonyl or arylalkylsulfonyl
für die Bedeutung von m = 0 zusätzlich für Thiocyanato, Halogen, Nitro, Cyano, Hydroxy, Halogenalkyl, Halogenalkenyl, Chlorsulfonyl, Alkoxy, Halogenalkoxy, Alkenyloxy, Halogenalkenyloxy, Alkyl- carbonyloxy, Formyl, Trialkylsilylethinyl, gegebenenfalls substituiertes Aryloxy oder für eine der folgenden Gruppiemngen steht:for the meaning of m = 0 additionally for thiocyanato, halogen, nitro, cyano, hydroxy, haloalkyl, haloalkenyl, chlorosulfonyl, alkoxy, haloalkoxy, alkenyloxy, haloalkenyloxy, alkylcarbonyloxy, formyl, trialkylsilylethynyl, optionally substituted aryloxy or for one of the following groups stands:
-NHR4, -NR R5, -NHNH2, -CONH2, -CSNH2, -CONR4R5, - SO2NR4R5, -CR6=NOR7, -CH(OH)R8 0der -CH(CN)OR9,-NHR 4 , -NR R 5 , -NHNH 2 , -CONH 2 , -CSNH 2 , -CONR 4 R 5 , - SO 2 NR 4 R 5 , -CR 6 = NOR 7 , -CH (OH) R8 0 d he -CH (CN) OR 9 ,
wobeiin which
R4 und R5 unabhängig voneinander für Wasserstoff, Cyano, Alkyl oder jeweils gegebenenfalls substituiertes Aryl oder Aralkyl stehen,R 4 and R 5 independently of one another represent hydrogen, cyano, alkyl or in each case optionally substituted aryl or aralkyl,
R6 für Wasserstoff oder Alkyl steht,R 6 represents hydrogen or alkyl,
R7 für Wasserstoff, Alkyl oder gegebenenfalls substituiertes Aralkyl steht,R 7 represents hydrogen, alkyl or optionally substituted aralkyl,
R8 für Alkyl oder Halogenalkyl steht undR 8 represents alkyl or haloalkyl and
R9 für Alkyl steht, für Wasserstoff, Amino, Halogen oder für eine der folgenden Gruppierungen steht:R 9 represents alkyl, represents hydrogen, amino, halogen or one of the following groups:
-NH-CO-R10, -NHR1 1, -OR12, -SR12 oder -NR13-CX-C(R14, R15, R16)-NH-CO-R 10 , -NHR 1 1 , -OR 12 , -SR 12 or -NR 13 -CX-C (R 14 , R 15 , R16)
wobeiin which
R10 für Alkyl, Halogenalkyl, Alkoxyalkyl oder jeweils gegebenen- falls substituiertes Phenyl, Phenoxy oder Pyridyl steht,R 10 represents alkyl, haloalkyl, alkoxyalkyl or optionally substituted phenyl, phenoxy or pyridyl,
R1 ! für Alkyl, Alkenyl, Alkinyl, Formyl, Alkylcarbonyl, Halogen- alkylcarbonyl oder Alkoxycarbonyl steht,R 1 ! represents alkyl, alkenyl, alkynyl, formyl, alkylcarbonyl, haloalkylcarbonyl or alkoxycarbonyl,
R12 für Alkyl, Alkenyl, Alkinyl, gegebenenfalls substituiertes Aralkyl, Dialkylaminoalkyl oder für die Gruppierung P(=Y)(OR17)(SR18) steht,R 12 represents alkyl, alkenyl, alkynyl, optionally substituted aralkyl, dialkylaminoalkyl or the grouping P (= Y) (OR 17 ) (SR 18 ),
wobeiin which
R17 und R18 unabhängig voneinander für Alkyl stehen undR 17 and R 18 are independently alkyl and
Y für Sauerstoff oder Schwefel steht,Y represents oxygen or sulfur,
R13 für Wasserstoff, Alkyl, Alkoxyalkyl, Propargyl, Allyl, Alkoxycarbonyl, Alkylcarbonyl, gegebenenfalls substituiertes Benzyl oder die Gruppierung -CO-C(R14, R15, R16) steht,R 13 represents hydrogen, alkyl, alkoxyalkyl, propargyl, allyl, alkoxycarbonyl, alkylcarbonyl, optionally substituted benzyl or the grouping -CO-C (R 14 , R 15 , R 16 ),
R14 für Wasserstoff, Alkyl, Halogenalkyl, Halogen oder gegebe- nenfalls substituiertes Phenyl steht und R15 für Wasserstoff, Alkyl, Halogenalkyl, Halogen, Halalkoxyal- kyl, Alkylthioalkyl, Alkylsulfinylalkyl, Alkylsulfonylalkyl, Alkoxy(alkoxy)ralkyl mit r = 0 bis 4, Hydroxy, Alkoxy- carbonylalkyl oder Alkoxy steht, oderR 14 represents hydrogen, alkyl, haloalkyl, halogen or optionally substituted phenyl and R 15 represents hydrogen, alkyl, haloalkyl, halogen, halalkoxyalkyl, alkylthioalkyl, alkylsulfinylalkyl, alkylsulfonylalkyl, alkoxy (alkoxy) r alkyl with r = 0 to 4, hydroxy, alkoxycarbonylalkyl or alkoxy, or
R1 und R15 gemeinsam mit dem Kohlenstoffatom, an das sie gebunden sind, für ein 3- bis 7-gliedriges Ringsystem mit gegebenenfalls bis zu zwei Heteroatomen stehen undR 1 and R 15 together with the carbon atom to which they are attached represent a 3- to 7-membered ring system with optionally up to two heteroatoms and
R16 für Hydroxy, Alkoxy, Halalkoxy, Alkoxy(alkoxy)p mit p= 1 bis 4 oder Halalkoxy(alkoxy)q mit q = 1 bis 4 steht, undR 16 stands for hydroxy, alkoxy, halalkoxy, alkoxy (alkoxy) p with p = 1 to 4 or halalkoxy (alkoxy) q with q = 1 to 4, and
X für Sauerstoff oder Schwefel steht, undX represents oxygen or sulfur, and
Ar für jeweils gegebenenfalls substituiertes Phenyl oder Pyridyl steht.Ar stands for optionally substituted phenyl or pyridyl.
2. Substituierte 3-Thiocarbamoylpyrazole gemäß Anspruch 1, dadurch gekennzeichnet, daß2. Substituted 3-thiocarbamoylpyrazole according to claim 1, characterized in that
R1 für H2N-CS- steht,R 1 stands for H 2 N-CS-,
m für die Zahlen 0 oder 1 steht,m represents the numbers 0 or 1,
für die Zahlen 0, 1 oder 2 steht,represents the numbers 0, 1 or 2,
R2 für (C,-C6)- Alkyl, (C2-C6)-Alkenyl, (C2-C6)-Alkinyl, Cyan-(CrC4)- alkyl, Thiocyanato-(CrC4)-alkyl, Nitro-(CrC4)-alkyl, (C,-C6)-R 2 for (C, -C 6 ) alkyl, (C 2 -C 6 ) alkenyl, (C 2 -C 6 ) alkynyl, cyano- (C r C 4 ) alkyl, thiocyanato- (C r C 4 ) -alkyl, nitro- (C r C 4 ) -alkyl, (C, -C 6 ) -
Alkylthio-(C , -C4)-alkyl, (C , -C6)-Alkylsulfmyl-(C -C4)-alkyl, (C , -Alkylthio- (C, -C 4 ) alkyl, (C, -C 6 ) alkylsulfmyl- (C -C 4 ) alkyl, (C, -
C6)-Alkylsulfonyl-(C j -C4)-alkyl, (C , -C4)-Halogenalkylthio-(C , -C4)- alkyl mit 1 bis 6 Halogenatomen, (Cι-C )-Halogenalkylsulfιnyl-(CC 6 ) -Alkylsulfonyl- (C j -C 4 ) -alkyl, (C, -C 4 ) -Halogenalkylthio- (C, -C 4 ) - alkyl with 1 to 6 halogen atoms, (Cι-C) -Halogenalkylsulfιnyl- ( C.
C )-alkyl mit 1 bis 6 Halogenatomen, (CrC )-Halogenalkylsulfonyl- (CrC4)-alkyl mit 1 bis 6 Halogenatomen, (C2-C6)-Alkenylthio-(Cj- C4)-alkyl, (C2-C6)-Alkenylsulfmyl-(C j -C4)-alkyl, (C2-C6)- Alkenyl- sulfonyl-(CrC4)-alkyl, (C2-C6)-Alkinylthio-(CrC4)alkyl, (C2-C6)- Alkinylsulfιnyl-(C , -C4)alkyl, (C2-C6)- Alkinylsulfonyl-(C j -C4)alkyl, (CrC4)-Alkoxy-carbonyl-(CrC4)-alkyl, (CrC4)-Halogenalkoxy- carbonyl-(Cj-C )-alkyl mit 1 bis 5 Halogenatomen, (C]-Cg)-Alkoxy- carbonyl, (CrC6)-Alkyl-carbonyl, (CrC6)-Alkoxy-(CrC4)-alkyl, (Cj-C6)-Halogenalkoxy-(C]-C )-alkyl mit 1 bis 6 Halogenatomen, (C ! -C4)-Alkoxy-(C ] -C4)-alkylthio-(C } -C4)-alkyl, (C j -C4)- Alkoxy- (C ! -C4)-alkylsulfιnyl-(C λ -C4)-alkyl, Alkoxy-(C j -C4)-alkylsulfonyl-C) -alkyl with 1 to 6 halogen atoms, (C r C) -haloalkylsulfonyl- (C r C 4 ) alkyl having 1 to 6 halogen atoms, (C 2 -C 6 ) alkenylthio- (C j - C 4 ) alkyl, (C 2 -C 6 ) alkenylsulfmyl- (C j -C 4 ) alkyl, (C 2 -C 6 ) alkenyl sulfonyl (C r C 4 ) alkyl, (C 2 -C 6 ) alkynylthio (C r C 4 ) alkyl, (C 2 -C 6 ) - Alkinylsulfιnyl- (C, -C 4 ) alkyl, (C 2 -C 6 ) - alkynylsulfonyl- (C j -C 4 ) alkyl, (C r C 4 ) -alkoxy-carbonyl- (C r C 4 ) alkyl , (C r C 4 ) -haloalkoxy-carbonyl- (Cj-C) -alkyl having 1 to 5 halogen atoms, (C ] -Cg) -alkoxy-carbonyl, (C r C 6 ) -alkyl carbonyl, (C r C 6 ) -alkoxy- (C r C 4 ) -alkyl, (C j -C 6 ) -haloalkoxy- (C ] -C) -alkyl having 1 to 6 halogen atoms, (C! -C 4 ) -alkoxy- ( C ] -C 4 ) alkylthio- (C } -C 4 ) alkyl, (C j -C 4 ) - alkoxy- (C ! -C 4 ) alkylsulfιnyl- (C λ -C 4 ) alkyl, alkoxy - (C j -C 4 ) alkylsulfonyl-
(C ! -C4)-alkyl, (C j -C4)-Halogenalkoxy-(C , -C4)-alkylthio-(C j -C4)- alkyl mit 1 bis 5 Halogenatomen, (CrC4)-Halogenalkoxy-(C]-C4)- alkylsulfιnyl-(Cj-C )-alkyl mit 1 bis 5 Halogenatomen, (C C )- Halogenalkoxy-(CrC )-alkylsulfonyl-(CrC )-alkyl mit 1 bis 5 Halo- genatomen, (CrC4)-Alkylamino-(C]-C4)-alkyl, Di-(CrC4)-alkyl- amino-(C!-C4)-alkyl, Tri-(CrC4)-alkylsilyl-(C]-C )-alkyl steht; oder für jeweils gegebenenfalls einfach bis fünffach, gleich oder verschieden substituiertes (Cß-C^-Cycloalkyl, (C5-C6)-Cycloalkenyl oder (C3-C6)-Cycloalkyl-(CrC2)-alkyl steht, wobei als Substituenten genannt seien:(C! -C 4 ) alkyl, (C j -C 4 ) haloalkoxy- (C, -C 4 ) alkylthio- (C j -C 4 ) alkyl with 1 to 5 halogen atoms, (C r C 4 ) haloalkoxy (C] -C4) - alkylsulfιnyl- (C j -C) alkyl having 1 to 5 halogen atoms, (CC) - haloalkoxy (C r C) alkylsulfonyl (C r C) alkyl having 1 to 5 halogen atoms, (C r C 4 ) -alkylamino- (C] -C 4 ) -alkyl, di- (C r C 4 ) -alkyl-amino- (C ! -C 4 ) -alkyl, tri - (C r C 4 ) alkylsilyl- (C] -C) alkyl; or in each case optionally monosubstituted to pentasubstituted by identical or different substituents (C ß ^ -C cycloalkyl, (C 5 -C 6) -cycloalkenyl or (C 3 -C 6) cycloalkyl (C r C -alkyl 2) , where the following may be mentioned as substituents:
(CrC4)- Alkyl, (Cj-C4)- Alkoxy, Halogen, (CrC4)-Halogenalkyl mit 1 bis 5 Halogenatomen und (Cj-C4)-Halogenalkoxy mit 1 bis 5 Halogenatomen; oder für jeweils gegebenenfalls einfach bis dreifach, gleich oder verschie- den substituiertes Phenyl, Phenyl-(Cj-C2)-alkyl steht, Phenoxy-(Cj-(C r C 4 ) alkyl, (C j -C 4 ) alkoxy, halogen, (C r C 4 ) haloalkyl having 1 to 5 halogen atoms and (Cj-C 4 ) haloalkoxy having 1 to 5 halogen atoms; or represents in each case optionally mono- to trisubstituted, identical or differently substituted phenyl, phenyl- (Cj-C 2 ) -alkyl, phenoxy- (C j -
C2)-alkyl, Phenylthio-(C j -C2)-alkyl, Phenylsulfmyl-(C ] -C2)-alkyl, Phenylsulfonyl-(C , -C2)-alkyl, Phenyl-(C , -C2)-alky loxy-(C , -C2)- alkyl, Phenyl-(C , -C2)-alkylthio-(C l -C2)-alkyl, Phenyl-(C , -C2)-alkyl- sulfιnyl-(C , -C2)-alkyl, Phenyl-(C , -C2)-alkylsulfonyl-(C { -C2)-alky 1, Pyridyl oder Pyridyl-(C]-C2)-alkyl steht, wobei als Phenyl- oder Pyri- dylsubstituenten genannt seien: Halogen, (CrC6)- Alkyl, (C2-C6)- Alkenyl, (CrC6)-Alkoxy, (C2-C6)- Alkenyloxy, (CrC4)-Alkylthio, (CrC4)-Alkylsulfmyl, (CrC4)- Alkylsulfonyl; (CrC6)-Halogenalkyl, (C2-C4)-Halogenalkenyl, (Cr C4)-Halogenalkoxy, (CrC4)-Halogenalkylthio, (CrC )-Halogenal- kylsulfmyl und (CrC )-Halogenalkylsulfonyl mit jeweils 1 bis 5C 2 ) alkyl, phenylthio- (C j -C 2 ) alkyl, phenylsulfmyl- (C ] -C 2 ) alkyl, phenylsulfonyl- (C, -C 2 ) alkyl, phenyl- (C, -C 2 ) -alky loxy- (C, -C 2 ) alkyl, phenyl- (C, -C 2 ) alkylthio- (C l -C 2 ) alkyl, phenyl- (C, -C 2 ) alkyl- sulfιnyl - (C, -C 2 ) -alkyl, phenyl- (C, -C 2 ) -alkylsulfonyl- (C { -C 2 ) -alkyl 1, pyridyl or pyridyl- (C ] -C 2 ) -alkyl, where the following may be mentioned as phenyl or pyridyl substituents: Halogen, (C r C 6 ) alkyl, (C 2 -C 6 ) alkenyl, (C r C 6 ) alkoxy, (C 2 -C 6 ) alkenyloxy, (C r C 4 ) alkylthio, ( C r C 4 ) alkylsulfmyl, (C r C 4 ) alkylsulfonyl; (C r C 6 ) haloalkyl, (C 2 -C 4 ) haloalkenyl, (C r C 4 ) haloalkoxy, (C r C 4 ) haloalkylthio, (C r C) haloalkylsulfmyl and (C r C) -haloalkylsulfonyl, each with 1 to 5
Halogenatomen; Cyano, Nitro, Hydroxy, Hydrazino, (CrC6)-Dialkyl- hydrazino, Amino, (CrC6)-Alkylamino, Di-(CrC6)-alkylamino, (Cr C6)- Alkylimino, (C j -C4)- Alky 1-carbonyl, (C j -C )- Alkyl-carbonyloxy , jeweils gegebenenfalls einfach bis dreifach, gleich oder verschieden durch Halogen, (CrC4)-Alkyl, (CrC4)-Halogenalkyl mit 1 bis 5Halogen atoms; Cyano, nitro, hydroxy, hydrazino, (C r C 6 ) -dialkyl-hydrazino, amino, (C r C 6 ) -alkylamino, di- (C r C 6 ) -alkylamino, (C r C 6 ) -alkylimino, (C j -C 4 ) - alkyl 1-carbonyl, (C j -C) - alkyl carbonyloxy, each optionally one to three times, identical or different by halogen, (C r C 4 ) alkyl, (C r C 4 ) Haloalkyl with 1 to 5
Halogenatomen, (Cj-C )-Alkoxy oder (C j -C )-Halogenalkoxy und (C]-C4)-Halogenalkylthio mit jeweils 1 bis 5 Halogenatomen substituiertes Phenyl oder Phenoxy, SF5 Halogen atoms, (Cj-C) alkoxy or (C j -C) haloalkoxy and (C ] -C 4 ) haloalkylthio each with 1 to 5 halogen atoms substituted phenyl or phenoxy, SF 5
oder die Gruppierung — Z— Nor the grouping - Z— N
R" wobeiR "where
R' und R" unabhängig voneinander für Wasserstoff oder (C]-C6)- Alkyl stehen undR 'and R "independently of one another represent hydrogen or (C ] -C 6 ) alkyl and
für -CO oder -SO2 steht,represents -CO or -SO 2 ,
für die Bedeutung von m = 0 für Thiocyanato, Chlor, Brom, Jod,for the meaning of m = 0 for thiocyanato, chlorine, bromine, iodine,
Nitro, Cyano, Hydroxy, Chlorsulfonyl, (CrC4)-Alkoxy, (C2-C )- Alkenyloxy; (CrC4)-Halogenalkyl, (C2-C4)-Halogenalkenyl, (Cr Nitro, cyano, hydroxy, chlorosulfonyl, (C r C 4 ) alkoxy, (C 2 -C) alkenyloxy; (C r C 4 ) haloalkyl, (C 2 -C 4 ) haloalkenyl, (C r
C )-Halogenalkoxy und (C2-C4)-Halogenalkenyloxy mit jeweils 1 bis 5 Halogenatomen; (CrC )-Alkyl-carbonyloxy, Formyl, Tri-(CrC4)- alkylsilylethinyl oder für gegebenenfalls einfach bis fünffach, gleich oder verschieden substituiertes Phenoxy steht, wobei als Substituenten die oben für R2 bereits genannten Phenylsubstituenten infrage kommen oder vorzugsweise für eine der folgenden Gruppierungen steht:C) haloalkoxy and (C 2 -C 4 ) haloalkenyloxy each having 1 to 5 halogen atoms; (C r C) -alkyl-carbonyloxy, formyl, tri- (C r C 4 ) -alkylsilylethynyl or optionally optionally up to five times, identical or differently substituted phenoxy, where as substituents the phenyl substituents already mentioned above for R 2 are possible or preferably stand for one of the following groups:
-NHR4, -NR4R5, -NHNH2, -CONH2, -CSNH2, -CONR R5, --NHR 4 , -NR 4 R 5 , -NHNH 2 , -CONH 2 , -CSNH 2 , -CONR R5, -
SO2NR4R5,SO 2 NR 4 R 5 ,
-CR6=NOR7, -CH(OH)R8 oder -CH(CN)OR9,-CR 6 = NOR 7 , -CH (OH) R 8 or -CH (CN) OR 9 ,
wobeiin which
R4 und R5 unabhängig voneinander für Wasserstoff, Cyano, (Cr C )-Alkyl oder für jeweils gegebenenfalls einfach bis fünffach, gleich oder verschieden substituiertes Phenyl oder Benzyl stehen, wobei als Substituenten die oben für R2 bereits genannten Phenylsubstituenten infrage kommen,R 4 and R 5 independently of one another represent hydrogen, cyano, (C r C) -alkyl or in each case optionally phenyl or benzyl which is monosubstituted to pentased, identically or differently, the phenyl substituents already mentioned above for R 2 being suitable,
R6 für Wasserstoff oder (C ] -C4)- Alkyl steht,R 6 represents hydrogen or (C ] -C 4 ) alkyl,
R7 für Wasserstoff, (CrC4)- Alkyl oder gegebenenfalls einfach bis fünf- fach, gleich oder verschieden substituiertes Benzyl steht, wobei alsR 7 represents hydrogen, (C r C 4 ) alkyl or optionally up to five times, identical or differently substituted benzyl, where as
Substituenten die oben für R2 bereits genannten Phenylsubstituenten infrage kommen,Substituents which are suitable for phenyl substituents already mentioned above for R 2 ,
R8 für (CrC4)-Alkyl oder (CrC4)-Halogenalkyl mit 1 bis 5 Halogenato- men steht,R 8 represents (C r C 4 ) -alkyl or (C r C 4 ) -haloalkyl with 1 to 5 halogen atoms,
R9 für (CrC4)-Alkyl steht,R 9 represents (C r C 4 ) alkyl,
R3 für Wasserstoff, Amino, Chlor, Brom, Jod oder für eine der folgenden Gruppierungen steht: -NH-CO-R10, -NHR1 1, -OR12, -SR12 oder -NR13-CX-C(R14, R15 R16),R 3 represents hydrogen, amino, chlorine, bromine, iodine or one of the following groups: -NH-CO-R 10 , -NHR 1 1 , -OR 12 , -SR 12 or -NR 13 -CX-C (R 14 , R 15 R 16 ),
wobeiin which
RIO für (CrC4)- Alkyl, (CrC4)-Halogenalkyl mit 1 bis 5 Halogenatomen, (C]-C4)-Alkoxy-(C]-C4)-alkyl oder für jeweils gegebenenfalls einfach bis fünffach, gleich oder verschieden substituiertes Phenyl, Phenoxy oder Pyridyl steht, wobei als Sub- stituenten die oben für R2 bereits genannten Phenylsubstituenten infrage kommen,RIO for (C r C 4 ) alkyl, (C r C 4 ) haloalkyl having 1 to 5 halogen atoms, (C ] -C 4 ) alkoxy- (C] -C 4 ) alkyl or for each in each case simply to phenyl, phenoxy or pyridyl which is substituted five times, identically or differently, where the phenyl substituents already mentioned above for R 2 are suitable as substituents,
Rl ! für (CrC4)- Alkyl, (C2-C4)-Alkenyl, (C2-C4)-Alkinyl, Formyl, (Cj-C4)-Alkyl-carbonyl, (Cj-C4)-Halogenalkyl-carbonyl mit 1 bis 5 Halogenatomen oder (C]-C )-Alkoxy-carbonyl steht,Rl ! for (C r C 4 ) alkyl, (C 2 -C 4 ) alkenyl, (C 2 -C 4 ) alkynyl, formyl, (C j -C 4 ) alkylcarbonyl, (Cj-C 4 ) -Halogenalkyl-carbonyl having 1 to 5 halogen atoms or (C] -C) -alkoxy-carbonyl,
Rl für (CrC4)-Alkyl, (C2-C4)-Alkenyl, (C2-C4)-Alkinyl, Di-(Cr R l for (C r C 4 ) alkyl, (C 2 -C 4 ) alkenyl, (C 2 -C 4 ) alkynyl, di- (C r
C )-alkylamino-(C]-C4)-alkyl; gegebenenfalls einfach bis fünffach, gleich oder verschieden substituiertes Pheny l-(Cj- C2)-alkyl steht, wobei als Substituenten die oben für R2 bereits genannten Phenylsubstituenten infrage kommen;C) alkylamino (C ] -C 4 ) alkyl; which is optionally monosubstituted to pentasubstituted by identical or different substituents Phenyl-l- (C j - C 2) alkyl, suitable substituents being the phenyl substituents already mentioned above for R 2 are suitable;
oder für die Gruppierung -P(=Y)(ORl 7)(SR18) steht,or stands for the grouping -P (= Y) (OR l 7 ) (SR 18 ),
wobeiin which
R17 und Rl 8 unabhängig voneinander für (C|-C4)-Alkyl stehen undR 17 and R l 8 independently of one another represent (C | -C 4 ) -alkyl and
Y für Sauerstoff oder Schwefel steht, R'3 für Wasserstoff, (CrC4)-Alkyl, (CrC4)-Alkoxy-(CrC4)- alkyl, Propargyl, Allyl, (CrC4)-Alkoxy-carbonyl, (CrC4)- Alkyl-carbonyl steht; oder für gegebenenfalls einfach bis fünffach, gleich oder verschieden substituiertes Benzyl steht, wobei als Substituenten die oben für R2 bereits genannten Phenylsubstituenten infrage kommen,Y represents oxygen or sulfur, R ' 3 is hydrogen, (C r C 4 ) -alkyl, (C r C 4 ) -alkoxy- (C r C 4 ) -alkyl, propargyl, allyl, (C r C 4 ) -alkoxy-carbonyl, (C r is C 4 ) -alkyl carbonyl; or represents optionally mono- to pentasubstituted, identically or differently substituted benzyl, where the phenyl substituents already mentioned above for R 2 are suitable as substituents,
oder für die Gruppierung -CO-C(R14, Rl 5, R16) steht,or represents the grouping -CO-C (R 14 , R l 5 , R 16 ),
R14 für Wasserstoff, (CrC4)- Alkyl, Halogen, (CrC4)-Halogenal- kyl mit 1 bis 5 Halogenatomen oder für gegebenenfalls einfach bis fünffach, gleich oder verschieden substituiertes Phenyl steht, wobei als Substituenten die oben für R2 bereits genannten Phenylsubstituenten infrage kommen,R 14 represents hydrogen, (C r C 4 ) -alkyl, halogen, (C r C 4 ) -haloalkyl having 1 to 5 halogen atoms or optionally optionally up to five times, identical or differently substituted phenyl, the substituents above are suitable for R 2 phenyl substituents already mentioned,
Rl5 für Wasserstoff, (CrC4)- Alkyl, Halogen, (C,-C4)-Halogenal- kyl und (C1-C4)-Halogenalkoxy-(C1-C4)-alkyl mit jeweils 1 bis 5 Halogenatomen, (CrC4)-Alkylthio-(CrC4)-alkyl, (Cr C4)-Alkylsulfmyl-(CrC4)-alkyl, (CrC4)- Alkylsulfonyl -(Cr C4)-alkyl, (CrC4)-Alkoxy-[(C1-C4)-alkoxy]r-(C1-C4)-alkyl mit r = 0 bis 2, Hydroxy, (Cj-C4)-Alkoxy-carbonyl-(CrC4)- alkyl und (C]-C4)-Alkoxy steht, oderRl5 for hydrogen, (C r C 4 ) alkyl, halogen, (C, -C 4 ) haloalkyl and (C 1 -C 4 ) haloalkoxy- (C 1 -C 4 ) alkyl, each with 1 to 5 halogen atoms, (C r C 4 ) -alkylthio- (C r C 4 ) -alkyl, (C r C 4 ) -alkylsulfmyl- (C r C 4 ) -alkyl, (C r C 4 ) -alkylsulfonyl - (C r C 4 ) alkyl, (C r C 4 ) alkoxy - [(C 1 -C 4 ) alkoxy] r - (C 1 -C 4 ) alkyl with r = 0 to 2, hydroxy, (C j -C 4 ) -alkoxy-carbonyl- (C r C 4 ) -alkyl and (C ] -C 4 ) -alkoxy, or
Rl und R15 gemeinsam mit dem Kohlenstoffatom, an das sie gebunden sind, für ein 5- bis 6- oder 7-gliedriges Ringsystem stehen, das gegebenenfalls bis zu zwei gleiche oder verschiedene Heteroatome, wie O-, S- oder N-Atome, enthalten kann,R 1 and R 15 together with the carbon atom to which they are attached represent a 5- to 6- or 7-membered ring system which may have up to two identical or different heteroatoms, such as O, S or N atoms may contain
R16 für Hydroxy, (CrC4)- Alkoxy, (CrC4)-Halogenalkoxy mit 1 bis 5 Halogenatomen oder (CrC4)-Alkoxy-[(CrC4)-alkoxy]q mit q = 1 oder 2 steht, X für Sauerstoff oder Schwefel steht undR 16 for hydroxy, (C r C 4 ) alkoxy, (C r C 4 ) haloalkoxy with 1 to 5 halogen atoms or (C r C 4 ) alkoxy - [(C r C 4 ) alkoxy] q with q = 1 or 2, X represents oxygen or sulfur and
Ar für jeweils gegebenenfalls einfach bis dreifach, gleich oder verschie- den substituiertes Phenyl oder Pyridyl steht, wobei als Substituenten jeweils die oben für R2 bereits genannten Phenylsubstituenten infrage kommen.Ar represents phenyl or pyridyl which is in each case monosubstituted to trisubstituted, identically or differently, the phenyl substituents already mentioned above for R 2 being suitable as substituents.
3. Substituierte 3-Thiocarbamoylpyrazole gemäß Anspruch 1, dadurch gekenn- zeichnet, daß3. Substituted 3-thiocarbamoylpyrazole according to claim 1, characterized in that
R1 für H2N-CS- steht,R 1 stands for H 2 N-CS-,
m für die Zahlen 0 oder 1 steht,m represents the numbers 0 or 1,
n für die Zahlen 0, 1 oder 2 steht,n represents the numbers 0, 1 or 2,
R2 für (CrC4)- Alkyl, (C2-C4)-Alkenyl, (C2-C4)-Alkinyl, Cyan-(C,-C2)- alkyl, Thiocyanato-(CrC2)-alkyl, Nitro-(CrC2)-alkyl, (CrC4)- Alkylthio-(CrC2)-alkyl, (Cι-C4)-Alkylsulfιnyl-(CrC2)-alkyl, (Cr R 2 for (C r C 4 ) alkyl, (C 2 -C 4 ) alkenyl, (C 2 -C 4 ) alkynyl, cyano- (C, -C 2 ) alkyl, thiocyanato- (C r C 2 ) -alkyl, nitro- (C r C 2 ) -alkyl, (C r C 4 ) -alkylthio- (C r C 2 ) -alkyl, (Cι-C 4 ) -alkylsulfιnyl- (C r C 2 ) - alkyl, (C r
C4)-Alkylsulfonyl-(C j -C2)-alkyl, (C , -C2)-Halogenalkylthio-(C -C2)- alkyl mit 1 bis 5 gleichen oder verschiedenen Halogenatomen aus der Reihe Fluor, Chlor und Brom, (C1-C2)-Halogenalkylsulfιnyl-(CrC2)- alkyl und (Cι-C2)-Halogenalkylsulfonyl-(CrC2)-alkyl mit jeweils 1 bis 5 gleichen oder verschiedenen Halogenatomen aus der ReiheC 4 ) -Alkylsulfonyl- (C j -C 2 ) alkyl, (C, -C 2 ) -Halogenalkylthio- (C -C 2 ) - alkyl with 1 to 5 identical or different halogen atoms from the series fluorine, chlorine and bromine , (C 1 -C 2 ) -Halogenalkylsulfιnyl- (C r C 2 ) - alkyl and (Cι-C 2 ) -Halogenalkylsulfonyl- (C r C 2 ) alkyl, each with 1 to 5 identical or different halogen atoms from the series
Fluor, Chlor und Brom, (C2-C4)-Alkenylthio-(CrC2)-alkyl, (C2-C4)- Alkinylthio-(C i -C2)-alky 1, (C , -C2)-Alkoxy-carbony 1-(C , -C2)-alkyl, (Cι-C2)-Halogenalkoxy-carbonyl-(CrC2)-alkyl mit 1 bis 5 gleichen oder verschiedenen Halogenatomen aus der Reihe Fluor, Chlor und Brom, (CrC4)-Alkoxy-carbonyl, (CrC4)-Alkyl-carbonyl, (CrC4)-Fluorine, chlorine and bromine, (C 2 -C 4 ) -alkenylthio- (C r C 2 ) -alkyl, (C 2 -C 4 ) -alkynylthio- (C i -C 2 ) -alkyl 1, (C, - C 2 ) -alkoxy-carbony 1- (C, -C 2 ) -alkyl, (-C-C 2 ) -haloalkoxy-carbonyl- (C r C 2 ) -alkyl with 1 to 5 identical or different halogen atoms from the fluorine series , Chlorine and bromine, (C r C 4 ) -alkoxy-carbonyl, (C r C 4 ) -alkyl-carbonyl, (C r C 4 ) -
Alkoxy-(C , -C2)-alky 1, (C , -C2)-Alkoxy-(C -C2)-alkylthio-(C -C2)- alkyl, (C1-C2)-Halogenalkoxy-(C1-C2)-alkylthio-(C1-C2)-alkyl mit 1 bis 5 gleichen oder verschiedenen Halogenatomen aus der Reihe Fluor, Chlor und Brom, (CrC2)-Alkylamino-(CrC2)-alkyl, Di-(Cr C2)-alkylamino-(Cj-C2)-alkyl steht: oder für jeweils gegebenenfalls einfach bis dreifach, gleich oder verschieden substituiertes Cyclopropyl, Cyclopentyl und Cyclohexyl steht, wobei als Substituenten genannt seien:Alkoxy- (C, -C 2 ) -alkyl 1, (C, -C 2 ) -alkoxy- (C -C 2 ) -alkylthio- (C -C 2 ) - alkyl, (C 1 -C 2 ) haloalkoxy- (C 1 -C 2 ) alkylthio- (C 1 -C 2 ) alkyl with 1 to 5 identical or different halogen atoms from the series fluorine, chlorine and bromine, (C r C 2 ) -alkylamino- (C r C 2 ) -alkyl, di- (C r C 2 ) -alkylamino- (C j -C 2 ) -alkyl is: or for in each case optionally monosubstituted to trisubstituted by identical or different substituents Cyclopropyl, cyclopentyl and cyclohexyl, where the following may be mentioned as substituents:
Methyl, Ethyl, Methoxy, Ethoxy, Fluor, Chlor, Brom, Trifluormethyl und Trifluormethoxy; oder für jeweils gegebenenfalls einfach bis dreifach, gleich oder verschieden substituiertes Phenyl, Benzyl, Phenoxymethyl, Phenoxyethyl, Phenylthiomethyl, Phenylthioethyl, Benzyloxymethyl, Benzylthio- methyl, Pyridyl oder Pyridylmethyl steht, wobei als Phenyl- bzw. Pyridylsubstituenten genannt seien: Fluor, Chlor, Brom, (CrC4)-Alkyl, Allyl, (CrC4)-Alkoxy, Allyloxy,Methyl, ethyl, methoxy, ethoxy, fluorine, chlorine, bromine, trifluoromethyl and trifluoromethoxy; or for phenyl, benzyl, phenoxymethyl, phenoxyethyl, phenylthiomethyl, phenylthioethyl, benzyloxymethyl, benzylthiomethyl, pyridyl or pyridylmethyl which are optionally monosubstituted to trisubstituted by identical or different substituents, where phenyl or pyridyl substituents are mentioned: fluorine, chlorine, bromine , (C r C 4 ) alkyl, allyl, (C r C 4 ) alkoxy, allyloxy,
(CrC2)-Alkylthio; (C,-C2)-Halogenalkyl oder (CrC2)-Halogenal- koxy oder (C j -C2)-Halogenalkylthio mit jeweils 1 bis 5 gleichen oder verschiedenen Halogenatomen aus der Reihe Fluor, Chlor und Brom; Cyano, Nitro, Hydroxy, Hydrazino, Dimethylhydrazino, Amino, Methylamino, Dimethylamino, Iminomethyl, (CrC )-Alkyl-carbonyl,(C r C 2 ) alkylthio; (C, -C 2 ) haloalkyl or (C r C 2 ) haloalkoxy or (C j -C 2 ) haloalkylthio each having 1 to 5 identical or different halogen atoms from the series fluorine, chlorine and bromine; Cyano, nitro, hydroxy, hydrazino, dimethylhydrazino, amino, methylamino, dimethylamino, iminomethyl, (C r C) alkylcarbonyl,
(Cj-C2)-Alkyl-carbonyloxy; jeweils gegebenenfalls einfach bis zweifach, gleich oder verschieden durch Fluor, Chlor, Brom, Methyl, Ethyl, Methoxy, Trifluormethyl, Trifluormethoxy oder Trifluorme- thylthio substituiertes Phenyl oder Phenoxy; SF5 oder die Gruppie-(C j -C 2 ) alkyl carbonyloxy; each phenyl or phenoxy optionally substituted once or twice, identically or differently, by fluorine, chlorine, bromine, methyl, ethyl, methoxy, trifluoromethyl, trifluoromethoxy or trifluoromethylthio; SF 5 or the group
wobei R' und R" unabhängig voneinander für Wasserstoff oder (CrC )- Alkyl stehen undin which R 'and R "independently of one another represent hydrogen or (C r C) alkyl and
Z für -CO oder -SO2 steht,Z represents -CO or -SO 2 ,
R2 für m = 0 für SCN, Chlor, Jod, Nitro, Cyano, Hydroxy, Chlorsulfonyl, (CrC2)- Alkoxy, Allyloxy, (CrC2)-Halogenalkyl oder (CrC2)-Halo- genalkoxy mit jeweils 1 bis 5 gleichen oder verschiedenen Halogenatomen aus der Reihe Fluor, Chlor und Brom; (Cj-C2)-Alkyl- carbonyloxy, Formyl, -C≡C-Si(CH3)3 steht; oder für gegebenenfalls einfach bis zweifach, gleich oder verschieden substituiertes Phenoxy steht, wobei als Substituenten die oben für R2 bereits genannten Substituenten infrage kommen; oder für -CONH2, -CSNH2, -CON(CH3)2, -CON(C2H5)2, -CH=NOCH3, -CH=NOC2H5, -CH(CH3)=NOCH3 und -CH(OH)CF3 steht,R 2 for m = 0 for SCN, chlorine, iodine, nitro, cyano, hydroxy, chlorosulfonyl, (C r C 2 ) alkoxy, allyloxy, (C r C 2 ) haloalkyl or (C r C 2 ) halo genalkoxy each having 1 to 5 identical or different halogen atoms from the series fluorine, chlorine and bromine; (C j -C 2 ) alkylcarbonyloxy, formyl, -C≡C-Si (CH 3 ) 3 ; or represents phenoxy which is monosubstituted or disubstituted in the same way or differently, where the substituents already mentioned for R 2 are suitable; or for -CONH 2 , -CSNH 2 , -CON (CH 3 ) 2 , -CON (C 2 H 5 ) 2 , -CH = NOCH 3 , -CH = NOC 2 H 5 , -CH (CH 3 ) = NOCH 3 and -CH (OH) CF 3 ,
R3 für Wasserstoff, Amino, Chlor, (Cj-C )-Alkylamino sowie für die Gruppierung -NH-CO-Rl° steht,R 3 represents hydrogen, amino, chlorine, (Cj-C) -alkylamino and the grouping -NH-CO-R 1 °,
wobeiin which
Rio besonders bevorzugt für (CrC4)- Alkyl, (CrC2)-Halogenalkyl mit 1 bis 5 gleichen oder verschiedenen Halogenatomen aus der Reihe Fluor, Chlor und Brom sowie für jeweils gegebenen- falls einfach bis zweifach, gleich oder verschieden substituiertes Phenyl und Phenoxy steht, wobei als Substituenten die oben für R2 bereits genannten Phenylsubstituenten infrage kommen undRio is particularly preferred for (C r C 4 ) -alkyl, (C r C 2 ) -haloalkyl having 1 to 5 identical or different halogen atoms from the series fluorine, chlorine and bromine and, if appropriate, in each case simply to twice, identical or different substituted phenyl and phenoxy, where the phenyl substituents already mentioned above for R 2 are suitable and
Ar für jeweils gegebenenfalls einfach bis dreifach, gleich oder verschieden durch Fluor, Chlor, Brom; (C]-C2)-Halogenalkyl und (Cj-C2)- Halogenalkoxy und (CrC2)-Halogenalkylthio und (Cj-C2)-Halogen- alkylsulfinyl und (Cj-C2)-Halogenalkylsulfonyl mit jeweils 1 bis 5 gleichen oder verschiedenen Halogenatomen aus der Reihe Fluor, Chlor und Brom; (CrC )- Alkyl, (CrC2)- Alkoxy, Hydrazino, Dime- thylhydrazino, Amino, Methylamino, Dimethylamino, Cyano, SF5 Ar for each optionally single to triple, identical or different by fluorine, chlorine, bromine; (C] -C 2 ) haloalkyl and (C j -C 2 ) - Haloalkoxy and (C r C 2 ) -haloalkylthio and (C j -C 2 ) -haloalkylsulfinyl and (Cj-C 2 ) -haloalkylsulfonyl each having 1 to 5 identical or different halogen atoms from the series fluorine, chlorine and bromine; (C r C) alkyl, (C r C 2 ) alkoxy, hydrazino, dimethylhydrazino, amino, methylamino, dimethylamino, cyano, SF 5
oder die Gmppierung or the assembly
wobeiin which
R' und R" unabhängig voneinander für Wasserstoff oder (Cj-C4)-R 'and R "independently of one another for hydrogen or (C j -C 4 ) -
Alkyl stehen undStand alkyl and
Z für CO oder SO2 steht,Z represents CO or SO 2 ,
substituiertes Phenyl oder Pyridyl steht.substituted phenyl or pyridyl.
4. Substituierte 3-Thiocarbamoylpyrazole gemäß Anspruch 1, dadurch gekennzeichnet, daß4. Substituted 3-thiocarbamoylpyrazole according to claim 1, characterized in that
R1 für H2N-CS- steht,R 1 stands for H 2 N-CS-,
m für die Zahlen 0 oder 1 steht,m represents the numbers 0 or 1,
n für die Zahlen 0, 1 oder 2 steht,n represents the numbers 0, 1 or 2,
R2 für CH3, C2H5, -CH2-CH=CH2, -C≡CH, -CH2-C≡CH, -CH2-CN, -CH2-SCN, -CH2-NO2, -CH2-S-CH3, -CH2-S-C2H5, -CH2CH2-S- CH3, -CH2CH2-S-C2H5, -CH2-SO-C2H5, -CH2-SO2-C2H5, -CFI2-S- CF3, CH2-SO-CF3, CH2-SO2-CF3, -CH2-S-CH2-CH=CH2, -CH2-S- CH2-C≡CH, -CH2-CO-OCH3, -CH2-CO-OC2H5, -(CH2)2-CO-OCH3, -(CH2)2-CO-OC2H5, -CH2-CO-OCF3, -CO-OCH3, -CO-OC2H5, - CO-CH3, -CO-C2H5, -CH2-OCH3, -CH2-OC2H5, -CH2-S-CH2CH2- O-C2H5, -CH2-S-CH2CH2-O-CH2CF3, -CH2-NHC2H5, -CH2CH2- N(CH3)2, -CH2CH2-N(C2H5)2, Cyclopropyl steht; oder für jeweils gegebenenfalls einfach bis dreifach, gleich oder verschieden substituiertes Benzyl, Benzyloxymethyl, Benzylthiomethyl, Phenoxymethyl, Phenoxyethyl, Phenylthiomethyl oder Phenylthioethyl steht, wobei jeweils als Phenylsubstituenten genannt seien: Fluor, Chlor, Trifluormethyl, Trifluormethoxy, Trifluormethylthio,R 2 for CH 3 , C 2 H 5 , -CH 2 -CH = CH 2 , -C≡CH, -CH 2 -C≡CH, -CH 2 -CN, -CH 2 -SCN, -CH 2 -NO 2 , -CH 2 -S-CH 3 , -CH 2 -SC 2 H 5 , -CH 2 CH 2 -S- CH 3 , -CH 2 CH 2 -SC 2 H 5 , -CH 2 -SO-C 2 H 5 , -CH 2 -SO 2 -C 2 H 5 , -CFI 2 -S- CF 3 , CH 2 -SO-CF 3 , CH 2 -SO 2 -CF 3 , -CH 2 -S-CH 2 - CH = CH 2 , -CH 2 -S- CH 2 -C≡CH, -CH 2 -CO-OCH 3 , -CH 2 -CO-OC 2 H 5 , - (CH 2 ) 2 -CO-OCH 3 , - (CH 2 ) 2 -CO-OC 2 H 5 , -CH 2 -CO-OCF 3 , -CO-OCH 3 , -CO-OC 2 H 5 , - CO-CH3, -CO-C 2 H 5 , -CH 2 -OCH 3 , -CH 2 - OC 2 H 5 , -CH 2 -S-CH 2 CH 2 - OC 2 H 5 , -CH 2 -S-CH 2 CH 2 -O-CH 2 CF 3 , -CH 2 -NHC 2 H 5 , -CH 2 CH 2 - N (CH 3 ) 2 , -CH 2 CH 2 -N (C 2 H 5 ) 2 , cyclopropyl; or stands for benzyl, benzyloxymethyl, benzylthiomethyl, phenoxymethyl, phenoxyethyl, phenylthiomethyl or phenylthioethyl, each optionally monosubstituted to trisubstituted in the same or different ways, phenyl substituents being mentioned in each case: fluorine, chlorine, trifluoromethyl, trifluoromethoxy, trifluoromethylthio,
Methoxy, Hydrazino, Dimethylhydrazino, Amino, Methylamino, Dimethylamino, Cyano, Methylthio, -CONH2, -CSNH2, Phenyl, Chlorphenyl, Fluorphenyl, Dichlorphenyl, Phenoxy, Chlorphenoxy, Fluorphenoxy und Dichlorphenoxy,Methoxy, hydrazino, dimethylhydrazino, amino, methylamino, dimethylamino, cyano, methylthio, -CONH 2 , -CSNH 2 , phenyl, chlorophenyl, fluorophenyl, dichlorophenyl, phenoxy, chlorophenoxy, fluorophenoxy and dichlorophenoxy,
R2 für m = 0 für SCN, Chlor, Jod, Nitro,R 2 for m = 0 for SCN, chlorine, iodine, nitro,
-OCH3, -CF3, -OCF3, -O-COCH3, -OH^-CI , -O-O-F,-OCH 3 , -CF 3 , -OCF 3 , -O-COCH 3 , -OH ^ -CI, -OOF,
-CSNH2, -CON(CH3)2, -CH=NOCH3 und -CH(OH)CF3 steht,-CSNH 2 , -CON (CH 3 ) 2 , -CH = NOCH 3 and -CH (OH) CF 3 ,
R3 für Wasserstoff, Amino, Chlor, -NHCH3,R 3 for hydrogen, amino, chlorine, -NHCH 3 ,
-NHC2H5, -NH-CO-CF3, , -NH-CO-OHQ>-F. -NHC2H5, -NH-CO-CF3,, -NH-CO-OHQ> -F.
steht, und stands, and
Ar für jeweils zweifach oder dreifach, gleich oder verschieden durch F, Cl, Br, CF3, OCF3, SCF3, SOCF3, SO2CF3, OCH2CF3, CH3 oder SF5 substituiertes Phenyl oder 2-Pyridyl steht. Verfahren zum Herstellen der substituierten 3-Thiocarbamoylpyrazole gemäß einem der Ansprüche 1 bis 4, dadurch gekennzeichnet, daß manAr represents phenyl or 2-pyridyl which is substituted twice or three times, identically or differently by F, Cl, Br, CF 3 , OCF3, SCF 3 , SOCF3, SO 2 CF 3 , OCH 2 CF 3 , CH 3 or SF 5 . Process for the preparation of the substituted 3-thiocarbamoylpyrazoles according to one of Claims 1 to 4, characterized in that
a) 3-Cyanopyrazol-Derivate der Formel (II)a) 3-cyanopyrazole derivatives of the formula (II)
in welcherin which
Ar, R2, R3, m und n die in einem der Ansprüche 1 bis 4 angegebeneAr, R 2 , R 3 , m and n are those specified in one of claims 1 to 4
Bedeutung haben,Have meaning
mit Schwefelwasserstoff, gegebenenfalls in Gegenwart eines Reaktionshilfsmittels und gegebenenfalls in Gegenwart eines Verdün- nungsmittels umsetzt;with hydrogen sulfide, if appropriate in the presence of a reaction auxiliary and if appropriate in the presence of a diluent;
oder daß manor that one
b) 3-Thiocarbamoylpyrazol-Derivate der Formel (III)b) 3-thiocarbamoylpyrazole derivatives of the formula (III)
ArAr
in welcher Ar die in einem der Ansprüche 1 bis 4 angegebene Bedeutung hat undin which Ar has the meaning given in one of claims 1 to 4 and
R3"l für eine der folgenden Gruppierungen steht:R 3 "l represents one of the following groupings:
OO
^ N 10" -N R1 1. -OR12 oder -NR13-CX-C(R14, R15, R16), H wobei^ N 10 "- N R1 1. -OR12 or -NR13-CX-C (R14, R15, R16), H where
Rio bis R! 6 und X die in einem der Ansprüche 1 bis 4 angegebeneR i o to R ! 6 and X that specified in one of claims 1 to 4
Bedeutung haben,Have meaning
mit Sulfenylhalogeniden der Formel (IV)with sulfenyl halides of the formula (IV)
Hal-S-R2 (IV)Hal-SR 2 (IV)
in welcherin which
R2 die in einem der Ansprüche 1 bis 4 angegebene Bedeutung hat undR 2 has the meaning given in one of claims 1 to 4 and
Hai für Halogen, insbesondere Chlor oder Brom steht,Shark represents halogen, especially chlorine or bromine,
gegebenenfalls in Gegenwart eines Verdünnungsmittels und gegebe- nenfalls in Gegenwart eines Reaktionshilfsmittels umsetzt;if appropriate in the presence of a diluent and, if appropriate, in the presence of a reaction auxiliary;
oder daß man c) die gemäß den Verfahren (a) oder (b) erhältlichen 3-Thiocarbamoyl- pyrazol-Derivate der Formel (Ia)or that one c) the 3-thiocarbamoylpyrazole derivatives of the formula (Ia) obtainable according to processes (a) or (b)
ArAr
(Ia), in welcher(Ia) in which
Ar, R2 und R3 die in einem der Ansprüche 1 bis 4 angegebene Bedeutung haben,Ar, R 2 and R 3 have the meaning given in one of claims 1 to 4,
mit Oxidationsmitteln gegebenenfalls in Gegenwart eines Verdünnungsmittels und gegebenenfalls in Gegenwart eines Katalysators oxi- diert.oxidized with oxidizing agents, if appropriate in the presence of a diluent and if appropriate in the presence of a catalyst.
6. 3-Thiocarbamoylpyrazol-Derivate der Formel (Ia)6. 3-thiocarbamoylpyrazole derivatives of the formula (Ia)
in welcherin which
Ar, R2 und R3 die in einem der Ansprüche 1 bis 4 angegebene Bedeutung haben. Verwendung von mindestens einem 3-Thiocarbamoylpyrazol gemäß einem der Ansprüche 1 bis 4 zur Bekämpfung von tierischen Schädlingen.Ar, R 2 and R 3 have the meaning given in one of claims 1 to 4. Use of at least one 3-thiocarbamoylpyrazole according to one of claims 1 to 4 for controlling animal pests.
Schädlingsbekämpfungsmittel, gekennzeichnet durch den Gehalt an mindestens einem 3-Thiocarbamoylpyrazol gemäß einem der Ansprüche 1 bis 4 und üblichen Streckmitteln. Pesticides, characterized by the content of at least one 3-thiocarbamoylpyrazole according to one of claims 1 to 4 and conventional extenders.
EP99925024A 1998-06-02 1999-05-21 Substituted 3-thiocarbamoylpyrazoles Withdrawn EP1084111A1 (en)

Applications Claiming Priority (3)

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DE19824487 1998-06-02
DE19824487A DE19824487A1 (en) 1998-06-02 1998-06-02 Substituted 3-thiocarbamoylpyrazoles
PCT/EP1999/003497 WO1999062886A1 (en) 1998-06-02 1999-05-21 Substituted 3-thiocarbamoylpyrazoles

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BR9910896A (en) 2001-02-13
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US6518296B1 (en) 2003-02-11
CN1311780A (en) 2001-09-05
JP2002517382A (en) 2002-06-18
AU4145599A (en) 1999-12-20
KR20010043814A (en) 2001-05-25
DE19824487A1 (en) 1999-12-09
CA2333715A1 (en) 1999-12-09
HK1039937A1 (en) 2002-05-17
AU750089B2 (en) 2002-07-11

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