EP1412334A1 - Derives de pyrazoline et leur utilisation comme agents de lutte contre les parasites - Google Patents

Derives de pyrazoline et leur utilisation comme agents de lutte contre les parasites

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Publication number
EP1412334A1
EP1412334A1 EP02758322A EP02758322A EP1412334A1 EP 1412334 A1 EP1412334 A1 EP 1412334A1 EP 02758322 A EP02758322 A EP 02758322A EP 02758322 A EP02758322 A EP 02758322A EP 1412334 A1 EP1412334 A1 EP 1412334A1
Authority
EP
European Patent Office
Prior art keywords
formula
spp
meanings given
cyano
pyrazoline derivatives
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Withdrawn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
EP02758322A
Other languages
German (de)
English (en)
Inventor
Fritz Maurer
Rainer Fuchs
Christoph Di Erdelen
Udo Reckmann
Andreas Turberg
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 CropScience AG
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Filing date
Publication date
Application filed by Bayer CropScience AG filed Critical Bayer CropScience AG
Publication of EP1412334A1 publication Critical patent/EP1412334A1/fr
Withdrawn legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
    • C07C255/24—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms containing cyano groups and singly-bound nitrogen atoms, not being further bound to other hetero atoms, bound to the same saturated acyclic carbon skeleton
    • C07C255/29—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms containing cyano groups and singly-bound nitrogen atoms, not being further bound to other hetero atoms, bound to the same saturated acyclic carbon skeleton containing cyano groups and acylated amino groups bound to the carbon skeleton
    • 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
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
    • A01N47/38—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the group >N—CO—N< where at least one nitrogen atom is part of a heterocyclic ring; Thio analogues thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
    • C07C255/24—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms containing cyano groups and singly-bound nitrogen atoms, not being further bound to other hetero atoms, bound to the same saturated acyclic carbon skeleton
    • C07C255/25—Aminoacetonitriles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
    • C07C271/04—Carbamic acid halides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C07C323/23—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
    • C07C323/31—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton
    • C07C323/33—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton having at least one of the nitrogen atoms bound to a carbon atom of the same non-condensed six-membered aromatic ring
    • C07C323/35—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton having at least one of the nitrogen atoms bound to a carbon atom of the same non-condensed six-membered aromatic ring the thio group being a sulfide group
    • C07C323/36—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton having at least one of the nitrogen atoms bound to a carbon atom of the same non-condensed six-membered aromatic ring the thio group being a sulfide group the sulfur atom of the sulfide group being further bound to an acyclic carbon atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C07C323/23—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
    • C07C323/39—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton at least one of the nitrogen atoms being part of any of the groups, X being a hetero atom, Y being any atom
    • C07C323/43—Y being a hetero atom
    • 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

Definitions

  • the present invention relates to new pyrazoline derivatives, ner processes for their preparation and their use as pesticides.
  • R 1 represents cyano, alkoxycarbonyl, carbamoyl, thiocarbamoyl, alkylaminocarbonyl or dialkylaminocarbonyl,
  • R 2 represents halogen, haloalkyl, alkoxy, haloalkoxy, alkylthio, haloalkylthio, alkylsulfonyl, haloalkylsulfmyl, haloalkylsulfonyl or cyano,
  • R 3 represents halogen, haloalkyl, alkoxy, haloalkoxy, alkylthio, haloalkylthio, haloalkylsulfmyl, haloalkylsulfonyl or cyano and
  • R 4 represents hydrogen, cyanomethyl or alkoxycarbonyl.
  • the Neritatien of the formula (I) can optionally be present as geometric and / or optical isomers, regioisomers or confectioning isomers or their isomer mixtures in different compositions. Both the pure isomers and the isomer mixtures are claimed according to the invention.
  • R 1 and R 2 have the meanings given above,
  • R 3 has the meanings given above if appropriate in the presence of a ner diluent and if appropriate in the presence of a catalyst;
  • R 1 , R 2 and R 3 have the meanings given above,
  • R 4 has the meanings given above and
  • R 1 , R 2 and R 3 have the meanings given above,
  • R 1 and R 2 have the meanings given above,
  • R 3 has the meanings given above
  • the new pyrazoline derivatives of the formula (I) have highly pronounced biological properties and above all to control animal pests, in particular insects, arachnids and nematodes, which are used in agriculture, in forests, in the protection of stocks and materials as well as in the hygiene sector are suitable.
  • Formula (I) generally defines the pyrazoline derivatives according to the invention.
  • R 1 preferably represents cyano, -CC 4 alkoxy-carbonyl, carbamoyl, thiocarbamoyl, -C-C 4 -alkylamino-carbonyl or di-C ⁇ -C 4 -alkylamino-carbonyl.
  • R 2 preferably represents fluorine, chlorine, bromine, iodine; -C-C 4 haloalkyl, C1-C4 haloalkoxy, C r C - alkylthio, C ⁇ haloalkylthio, C 1 -C alkylsulfonyl, CC ⁇ haloalkylsulfonyl or cyano.
  • R 3 preferably represents fluorine, chlorine, bromine, iodine; -C-C 4 haloalkyl, Cj-C 4 haloalkoxy, C j -C haloalkylthio, C i -C haloalkylsulfmyl, C 1 -C 4 haloalkylsulfonyl or cyano.
  • R 4 preferably represents hydrogen, cyanomethyl or C jC -alkoxy-carbonyl.
  • R 1 particularly preferably represents cyano, -CC 4 -alkoxy-carbonyl, carbamoyl, thiocarbamoyl, -C-C2-alkylamino-carbonyl or di- -C-C2-alkylamino-carbonyl.
  • R 2 particularly preferably represents fluorine, chlorine, bromine, iodine, cyano; -C-C2-alkyl thio, C j ⁇ -alkylsulfonyl and for Cj -C2-haloalkyl, C j ⁇ -haloalkoxy, C ⁇ -C2-haloalkylthio or C ⁇ -C 2 -haloalkylsulfonyl, each with 1 to 5 identical or different halogen atoms from the series fluorine, chlorine and bromine.
  • R 3 particularly preferably represents chlorine, bromine, iodine, cyano; as well as for C1-C2-haloalkyl, Ci ⁇ -haloalkoxy, C ] -C2-haloalkylthio, Ci ⁇ -haloalkylsulfmyl or C ! -C2-Haloalkylsulfonyl, each with 1 to 5 identical or different halogen atoms from the fluorine, chlorine and bromine series.
  • R 4 particularly preferably represents hydrogen, cyanomethyl or C1-C4-alkoxycarbonyl.
  • R 4 represents hydrogen or CH 2 CN.
  • R 2 represents halogen, preferably fluorine, chlorine, bromine or iodine, particularly preferably fluorine, chlorine or bromine, very particularly preferably chlorine.
  • carbon radicals such as alkyl - are also straight-chain or branched as far as possible, also in conjunction with heteroatoms such as alkoxy.
  • reaction sequence of process (a) according to the invention can be carried out by the following formula scheme can be reproduced:
  • Formula (II) provides a general definition of the pyrazolines to be used as starting materials for carrying out processes (a) and (c) according to the invention.
  • R 1 and R 2 preferably or particularly preferably have those meanings which have already been mentioned as preferred or particularly preferred for these radicals in connection with the description of the compounds of the formula (I) according to the invention.
  • R 1 and R 2 have the meanings given above,
  • Alk represents C r C 4 alkyl
  • Halogenated hydrocarbons e.g. Methylene chloride or ethylene chloride
  • temperatures between 0 ° C and 120 ° C, preferably between 20 ° C and 80 ° C (see e.g. EP-A 0 546 420) and the resulting dialkylaminoalkyl ketones of the formula (VIII)
  • R 1 , R 2 and Alk have the meanings given above, optionally isolated and reacted in a second stage with hydrazine (hydrate) in the presence of an inert organic solvent (preferably alcohols, such as methanol or ethanol) at temperatures between 0 ° C. and 80 ° C., preferably between 20 ° C. and 50 ° C. (see also the manufacturing examples).
  • an inert organic solvent preferably alcohols, such as methanol or ethanol
  • Formula (III) provides a general definition of the isocyanates to be used as starting materials in process (a) according to the invention.
  • R 3 preferably or particularly preferably has those meanings which have already been associated with the description of the compounds of the invention
  • the isocyanates of the formula (III) are generally known compounds of organic chemistry and / or can be obtained in a generally known manner.
  • Formula (VI) provides a general definition of the substituted acetophenones to be used as starting materials for carrying out process (d) according to the invention.
  • R 1 and R 2 preferably or particularly preferably have those meanings which have already been mentioned as preferred or particularly preferred for these radicals in connection with the description of the compounds of the formula (I) according to the invention.
  • R 1 has the meanings given above,
  • an organic or inorganic base eg potassium carbonate
  • an inert organic solvent eg acetonitrile
  • Formula (VII) provides a general definition of the bis-dialkylaminomethanes to be used as starting materials in process (d) according to the invention.
  • Alk preferably represents methyl.
  • Bis-dialkylaminomethanes of the formula (VII) are generally known compounds of organic chemistry and / or can be obtained in a generally known manner.
  • Formula (IX) provides a general definition of the haloacetophenones to be used as starting materials for carrying out process (e) according to the invention.
  • R 2 preferably or particularly preferably has those meanings which are already in connection with the description of the invention Ner compounds of the formula (I) were mentioned as preferred or particularly preferred for this radical.
  • Shark 2 is preferably chlorine or bromine.
  • Formula (X) provides a general definition of the pyrazoles to be used as starting materials in the ner process (e) according to the invention.
  • R 1 preferably or particularly preferably has those meanings which have already been mentioned as preferred or particularly preferred for this radical in connection with the description of the novel compounds of the formula (I) according to the invention.
  • haloacetophenones of the formula (IX) and the pyrazoles of the formula (X) are generally known compounds of organic chemistry and / or can be obtained in a generally known manner.
  • R 5 and R 6 independently of one another represent hydrogen or alkyl
  • R 2 has the meanings given above
  • mineral acids such as preferably hydrochloric acid or
  • R 2 has the meanings given above
  • R 5 and R 6 have the meanings given above,
  • an inert, organic solvent for example methylene chloride or tetrahydrofuran
  • an inert, organic solvent for example methylene chloride or tetrahydrofuran
  • the ammonia or the amine is used in excess, which also have the function of a base here (cf. also the preparation examples).
  • Formula (VIb) provides a general definition of the substituted acetophenones to be used as starting materials for carrying out process (f) according to the invention.
  • R 2 preferably or particularly preferably has those meanings which have already been mentioned as preferred or particularly preferred for this radical in connection with the description of the compounds of the formula (I) according to the invention.
  • substituted acetophenones of the formula (VIb) are likewise compounds of the invention and can be obtained by process (e).
  • Formula (XI) generally defines the amines to be used as starting materials in process (f) according to the invention.
  • R 5 and R 6 independently of one another preferably represent hydrogen or Cj-C 4 - alkyl, particularly preferably represents hydrogen or C -C 2 alkyl!.
  • the amines of the formula (XI) are generally known compounds of organic chemistry.
  • Formula (IV) provides a general definition of the halides to be used as starting materials for carrying out process (b) according to the invention.
  • R 4 preferably or particularly preferably has those meanings which have already been mentioned as preferred or particularly preferred for this radical in connection with the description of the compounds of the formula (I) according to the invention.
  • Shark 1 preferably represents chlorine or bromine.
  • the halides of the formula (IV) are generally known compounds of organic chemistry.
  • Formula (V) provides a general definition of the carbamic acid chlorides to be used as starting materials in process (c) according to the invention.
  • R 3 preferably or particularly preferably has those meanings which have already been mentioned as preferred or particularly preferred for this radical in connection with the description of the compounds of the formula (I) according to the invention.
  • carbamic acid chlorides of the formula (V) are known (cf. e.g. DE 27 30 325). Not yet known and also the subject of this application are carbamic acid chlorides of the formula (Va)
  • R 7 represents haloalkyl, haloalkoxy or haloalkylthio, preferably the corresponding preferred meanings of R 3 .
  • the carbamic acid chlorides of the formula (Va) are obtained, for example, by
  • phosgene in the presence of an inert organic diluent (e.g. toluene) and in the presence of a base (preferably tertiary organic amines such as triethylamine) at temperatures between -10 ° C and
  • an inert organic diluent e.g. toluene
  • a base preferably tertiary organic amines such as triethylamine
  • R 7 has the meanings given above
  • Process (a) according to the invention is preferably carried out using diluents.
  • diluents Practically all inert organic solvents can be used as diluents. These preferably include aliphatic ones and aromatic, optionally halogenated hydrocarbons such as pentane, 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, methyl ether tert-butyl ether, methyl tert-amyl ether, glycol dimethyl ether and diglycol dimethyl ether, tetrahydrofuran and dioxane, ketones such as acetone, methyl ethyl
  • Process (a) according to the invention is preferably also carried out using a catalyst.
  • a catalyst In particular, tertiary organic amines such as triethylamine are suitable as catalysts.
  • reaction temperatures in process (a) according to the invention can be varied within a substantial range. In general, temperatures between 0 ° C and 120 ° C, preferably at temperatures between 20 ° 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 starting materials are generally used in approximately equimolar amounts. However, it is also possible to use one of the two components used in a smaller excess. Working up is carried out using customary methods (cf. the production examples).
  • Suitable diluents are all inert organic solvents. These preferably include aliphatic and aromatic, optionally halogenated hydrocarbons such as pentane, 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, tetrahydrofuran and dioxane, ketones such as acetone, methyl ethyl, methyl isopropyl or methyl isobutyl ketone, esters such as methyl acetate or
  • Bases which can be used in carrying out processes (b) and (c) according to the invention are all acid binders which can customarily be used for such reactions.
  • Alkali metal and alkaline earth metal hydrides such as lithium, sodium, potassium or calcium hydride
  • Alkali metal and alkaline earth metal hydroxides such as lithium, sodium, potassium or calcium hydroxide
  • Alkali metal and alkaline earth metal carbonates or bicarbonates such as sodium or potassium carbonate or bicarbonate or calcium carbonate
  • Alkali metal acetates such as sodium or potassium acetate, alkali metal alcoholates, such as sodium or potassium tert-butoxide
  • basic nitrogen compounds such as trimethylamine, triethylamine, tripropylamine, tributylamine, diisobutylamine, dicyclohexylamine, ethyldiisopropylamine, ethyldicyclohexylamine, N, N-dimethylbenzylamine, N, N
  • reaction temperatures in process (b) according to the invention can be varied within a substantial range. In general, temperatures between 0 ° C and 120 ° C, preferably at temperatures between 20 ° C and 80 ° C.
  • Process (b) according to the invention is generally carried out under normal pressure. However, it is also possible to work under increased or reduced pressure.
  • the starting materials are generally used in approximately equimolar amounts. However, it is also possible to use the halide and the base in excess. Working up is carried out using customary methods (cf. the production examples).
  • reaction temperatures in process (c) according to the invention can be varied within a substantial range. In general, temperatures between - 10 ° C and + 130 ° C, preferably at temperatures between 0 ° C and 110 ° C.
  • Process (c) according to the invention is generally carried out under normal pressure. However, it is also possible to work under increased or reduced pressure.
  • the starting materials are generally used in approximately equimolar amounts. However, it is also possible to use the chloride and the base in excess. Working up is carried out using customary methods (cf. the production examples).
  • the active substances are suitable for controlling animal pests, especially insects,
  • the pests mentioned above include: From the order of the Isopoda, for example Oniscus asellus, Armadillidium vulgare, Porcellio scaber.
  • Thysanura e.g. Lepisma saccharina.
  • Phthiraptera e.g. Pediculus humanus corporis, Haematopinus spp., Linognathus spp., Trichodectes spp., Damalinia spp.
  • Thysanoptera e.g. Hercinothrips femoralis, Thrips tabaci
  • Trialeurodes vaporariorum Aphis gossypii, Brevicoryne brassicae, Cryptomyzus ribis, Aphis fabae, Aphis pomi, Eriosoma lanigerum, Hyalopterus arundinis,
  • Hymenoptera e.g. Diprion spp., Hoplocampa spp., Lasius spp., Monomorium pharaonis, Vespa spp.
  • Scorpio maurus Latrodectus mactans, Acarus siro, Argas spp., Ornithodoros spp., Dermanyssus gallinae, Eriophyes ribis, Phyllocoptruta oleivora, Boophilus spp., Rhipicephalus spp., Amblyomma spp., ., Psoroptes spp., Chorioptes spp., Sarcoptes spp., Tarsonemus spp., Bryobia praetiosa, Panonychus spp., Tetranychus spp., Hemitarsonemus spp., Brevipalpus spp.
  • the plant-parasitic nematodes include, for example, Pratylenchus spp., Radopholus similis, Ditylenchus dipsaci, Tylenchulus semipenetrans, Heterodera spp., Globodera spp., Meloidogyne spp., Aphelenchoides spp., Longidorus spp., Tripusichpp. Spp., Xiphinema spp.
  • the substances according to the invention can be used with particularly good success for combating plant-damaging insects, such as e.g. against the larvae of the cucumber beetle (Diabrotica balteata), the caterpillars of the cotton capsule worm (Heliothis virescens), the larvae of the horseradish beetle (Phaedon cochleariae), the caterpillars of the cockroach (Plutella xylostella) and caterpillars of the army worm
  • plant-damaging insects such as e.g. against the larvae of the cucumber beetle (Diabrotica balteata), the caterpillars of the cotton capsule worm (Heliothis virescens), the larvae of the horseradish beetle (Phaedon cochleariae), the caterpillars of the cockroach (Plutella xylostella) and caterpillars of the army worm
  • the substances according to the invention also show a very good duration of action, e.g. against the caterpillars of the cotton capsule worm (Heliothis virescens) or the caterpillars of the army worm (Spodoptera frugiperda).
  • the compounds according to the invention can also be used in certain concentrations or application rates as herbicides and microbicides, for example as fungicides, antifungals and bactericides. If appropriate, they can also be used as intermediates or precursors for the synthesis of further active compounds.
  • plants and parts of plants can be treated.
  • Plants are understood here to mean all plants and plant populations, such as desired and unwanted wild plants or crop plants (including naturally occurring crop plants).
  • Crop plants can be plants which can be obtained by conventional breeding and optimization methods or by biotechnological and genetic engineering methods or combinations of these methods, including the transgenic plants and including those which can or cannot be protected by plant breeders' rights
  • Plant varieties Under plant parts, all above-ground and underground Parts and organs of the plants, such as sprout, leaf, flower and root, are to be understood, examples being leaves, needles, stems, stems, flowers, fruiting bodies, fruits and seeds, and roots, tubers and rhizomes.
  • the plant parts also include crops and vegetative and generative propagation material, for example cuttings, tubers, rhizomes, offshoots and
  • the treatment of the plants and parts of plants with the active compounds according to the invention is carried out directly or by acting on their surroundings, living space or storage space according to the customary treatment methods, e.g. by dipping, spraying,
  • the active ingredients can be converted into the customary formulations, such as solutions, emulsions, wettable powders, suspensions, powders, dusts, pastes, soluble powders, granules, suspension emulsion concentrates, active ingredient-impregnated natural and synthetic substances and very fine encapsulations in polymers substances.
  • formulations are made in a known manner, e.g. by mixing the active ingredients with extenders, that is liquid solvents and / or solid
  • Carriers where appropriate using surface-active agents, that is to say emulsifiers and / or dispersants and / or foam-generating agents.
  • water is used as an extender, e.g. also organic
  • Solvents are 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 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.
  • ketones such as Acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone
  • strongly polar solvents such as dimethylformamide and dimethyl sulfoxide
  • Possible solid carriers are: e.g. Ammonium salts and natural rock flours, such as kaolins, clays,
  • Talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic rock powder, such as highly disperse silica, aluminum oxide and silicates, are suitable as solid carriers for granules: e.g. broken and fractionated natural rocks such as calcite, marble, pumice, sepiolite, dolomite and synthetic granules from inorganic and organic flours and granules from organic material such as sawdust, coconut shells, corn cobs and tobacco stems; as emulsifying and / or foaming agents are possible: e.g.
  • non-ionic and anionic emulsifiers such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, e.g. Alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates and protein hydrolyzates;
  • Possible dispersants are: e.g. Lignin sulfite liquor and methyl cellulose.
  • Adhesives such as carboxymethyl cellulose, natural and synthetic powdery, granular or latex-shaped polymers, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, and natural phospholipids such as cephalins and lecithins and synthetic phospholipids can be used in the formulations.
  • Other additives can be mineral and vegetable oils.
  • Dyes such as inorganic pigments, 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 compounds according to the invention can also be used in a mixture with known fungicides, bactericides, acaricides, nematicides or insecticides, in order, for example, to broaden the activity spectrum or to prevent the development of resistance. In many cases, synergistic effects are obtained, ie the effectiveness of the mixture is greater than that
  • Calcium polysulphide carpropamid, capsimycin, captafol, captan, carbendazim, carbonyl xin, carvone, chinomethionat (Quinomethionat) Chlobenthiazon, chlorfenazole, chlorides roneb, chloropicrin, chlorothalonil, chlozolinate, Clozylacon, Cufraneb, cymoxanil, cyproconazole, cyprodinil, cyprofuram, debacarb , Dichlorophene, diclobutrazole, diclofluanide, diclomezin, dicloran,
  • Iodocarb Ipconazol
  • Iprobefos IBP
  • Iprodione Iprovalicarb
  • Irumamycin Iprobefos
  • copper preparations such as: copper hydroxide, copper phthalate, copper oxychloride, copper sulfate, copper oxide, oxy-copper and
  • Mancopper Mancozeb, Maneb, Meferimzone, Mepanipyrim, Mepronil, Metalaxyl,
  • Metconazole methasulfocarb, methfuroxam, metiram, metomeclam, metsulfovax,
  • Oxadixyl Oxamocarb, Oxolinicacid, Oxycarboxim, Oxyfenthiin,
  • Paclobutrazole pefurazoate, penconazole, pencycuron, phosdiphen, picoxystrobin,
  • Tebuconazole Tebuconazole, tecloftalam, tecnazen, tetcyclacis, tetraconazole, thiabendazole,
  • Thicyofen Thifluzamide, Thiophanate-methyl, Thiram, Tioxymid, Tolclofos-methyl, Tolylfluanid, Triadimefon, Triadimenol, Triazbutil, Triazoxid, Trichlamid, Tricyclazol,
  • Tridemorph Tridemorph, trifloxystrobin, triflumizole, triforin, triticonazole,
  • N- (2-chloro-4-nitrophenyl) -4-methyl-3-nitro-benzenesulfonamide N- (4-cyclohexylphenyl) -1, 4,5,6-tetrahydro-2-pyrimidinamine, N- (4-hexylphenyl ) -l, 4,5,6-tetrahydro-2-pyrimidinamine, N- (5-chloro-2-methylphenyl) -2-methoxy-N- (2-oxo-3-oxazolidinyl) acetamide, N- (6 methoxy) -3-pyridyl) cyclopropanecarboxamide,
  • Chloethocarb Chlorethoxyfos, Chlorfenapyr, Chlorfenvinphos, Chlorfluazuron, Chlormephos, Chlo ⁇ yrifos, Chlo ⁇ yrifos M, Chlovaporthrin, Chromafenozide, Cis-Resmethrin, Cispermethrin, Clocythrin, Cloethocarb, Clofentezyan, Cyclophrine, Cyclophrine, Cyclophrinine, Clothianhrinin, Cytophrine, Clothianhrinin, Cyclophrinine .
  • Fenamiphos Fenazaquin, Fenbutatin oxide, Fenitrothion, Fenothiocarb, Fenoxacrim, Fenoxycarb, Fenpropathrin, Fenpyrad, Fenpyrithrin, Fenpyroximate, Fenvalerate, Fipronil, Fluazuron, Flubrocythrinate, Flucycloxuron, Flcythrinate, Fluftoxinhrininate, Fufonoxhrhrininate, Fumetoxinhrininate, Fumetoxin , Furathiocarb,
  • Halofenozide HCH, Heptenophos, Hexaflumuron, Hexythiazox, Hydroprene, Imidacloprid, Indoxacarb, Isazofos, Isofenphos, Isoxathion, Ivermectin, Kernpolyederviruses Lambda-cyhalothrin, Lufenuron Malathion, Mecarbam, Metaldehyde, Methamidophyllis, Methamidophosphate, Methamidophosphate
  • Metharhizin flavoviride methidathione, methiocarb, methoprene, methomyl, methoxyfenozide, metolcarb, metoxadiazone, Mevinphos, Milbemectin, milbemycin, Monocrotophos, Naled, Nitenpyram, Nithiazine, Novaluron Omethoat, Oxamyl Myd
  • Paecilomyces fumosoroseus Parathion A, Parathion M, Permethrin, Phenthoat, Phorat, Phosalone, Phosmet, Phosphamidon, Phoxim, Pirimicarb, Pirimiphos A, Pirimiphos M, Profenofos, Promecarb, Propargite, Propoxur, Prothiofos, Prothrohrinos, Pothrohrinos, Pothrohrine, Pothrohrinate , Pyridaben, pyridathione, pyrimidifen, pyriproxyfen,
  • 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 that increase the effectiveness of the active ingredients 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.
  • plants and their parts can be treated according to the invention.
  • plant species and plant cultivars and their parts occurring wildly or obtained by conventional biological breeding methods, such as crossing or protoplast fusion, are treated.
  • transgenic plants and plant cultivars which have been obtained by genetic engineering methods, if appropriate in combination with conventional methods (genetic modified organisms) and their parts are treated.
  • the term “parts” or “parts of plants” or “parts of plants” was explained above. Plants of the plant varieties which are in each case commercially available or in use are particularly preferably treated according to the invention.
  • Plant cultivars are understood to mean plants with new properties (“traits”) which have been cultivated both by conventional breeding, by mutagenesis or by recombinant DNA techniques. These can be cultivars, bio- and genotypes.
  • the treatment according to the invention can also result in superadditive (“synergistic”) effects.
  • superadditive for example, reduced application rates and or widening the spectrum of action and / or strengthening the effect of the substances and agents which can be used according to the invention, better plant growth, increased tolerance to high or low temperatures, increased tolerance to dryness or to water or soil salt content, increased flowering performance, easier harvesting, acceleration of ripeness, higher crop yields, higher quality and / or higher
  • Nutritional value of the harvested products higher shelf life and / or workability of the harvested products possible, which go beyond the effects that are actually to be expected.
  • the preferred transgenic plants or plant cultivars to be treated according to the invention include all plants which have received genetic material through the genetic engineering modification, which gives these plants particularly advantageous, valuable properties (“traits”). Examples of such properties are better plant growth, increased tolerance to high or low temperatures, increased tolerance to drought or to water or soil salt content, increased flowering performance, easier harvesting, acceleration of ripening, higher harvest yields, higher quality and / or higher nutritional value of the harvested products, higher shelf life and / or Machinability of the harvested products Further and particularly highlighted examples of such properties are an increased defense of the plants against animal and microbial pests, such as against insects, mites, phytopathogenic fungi, Bacteria and / or viruses and an increased tolerance of the plants to certain herbicidal active ingredients.
  • the important cultivated plants such as cereals (wheat, rice), corn, soybeans, potatoes, cotton, rapeseed and fruit plants (with the fruits apples, pears, citrus fruits and grapes) are mentioned as examples of transgenic plants, with corn, soybeans , Potato, cotton and rapeseed are highlighted.
  • the properties (“traits”) which are particularly emphasized are the plants' increased defense against insects by toxins arising in the plants, in particular those which are caused by the genetic material from Bacillus thuringiensis (for example by the genes Cry ⁇ A (a), Cry ⁇ A (b), Cry ⁇ A (c), CryllA, CrylllA, CryIIIB2, Cry9c, Cry2Ab, Cry3Bb and CrylF as well as their combinations) are produced in the plants (hereinafter "Bt plants”).
  • Bt plants The increased defense of plants against fungi, bacteria and viruses by systemic acquired resistance (SAR), systemin, phytoalexins, elicitors and resistance genes and correspondingly expressed proteins and toxins are also particularly emphasized as properties (“traits”).
  • Traits are also particularly emphasized the increased tolerance of the plants to certain herbicidal active ingredients, for example imidazolinones, sulfonylureas, glyphosate or phosphinotricin (for example” PAT "gene).
  • herbicidal active ingredients for example imidazolinones, sulfonylureas, glyphosate or phosphinotricin (for example” PAT "gene).
  • the genes which impart the desired properties can also occur in combinations with one another in the transgenic plants. Examples of “Bt plants” are maize varieties,
  • Cotton varieties, soy varieties and potato varieties named under the trade names YIELD GARD® (e.g. corn, cotton, soy), KnockOut® (e.g. corn), StarLink® (e.g. corn), Bollgard® (cotton), Nucotn® (cotton) and NewLeaf ® (potato) are sold.
  • Examples of herbicide-tolerant plants include maize, cotton and soybeans, which are among the
  • plants listed can be treated particularly advantageously according to the invention with the compounds of the general formula (I) or the active compound mixtures according to the invention.
  • the preferred ranges given above for the active substances or mixtures also apply to the treatment of these plants. Plant treatment with the compounds or mixtures specifically listed in the present text should be particularly emphasized.
  • 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 Hangings, featherlings and fleas.
  • animal parasites ectoparasites
  • tick ticks leather ticks
  • mites running mites
  • flies stinging and licking
  • parasitic fly larvae lice, hair Hangings, featherlings and fleas.
  • Xenopsylla spp. Ceratophyllus spp. From the order of the Heteropterida, for example Cimex spp., Triatoma spp., Rhodnius spp., Panstrongylus spp.
  • 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., Raillietssus spp., ., Sternostoma spp., Varroa spp. From the order of the Actinedida (Prostigmata) and Acaridida (Astigmata) e.g.
  • the active compounds of the formula (I) according to the invention are also suitable for controlling arthropods which are used in agricultural animals, e.g. Cattle, sheep, goats, horses, pigs, donkeys, camels, buffalo, rabbits, chickens, turkeys, ducks, geese, bees, other pets such as e.g. Dogs, cats, house birds, aquarium fish and so-called experimental animals, such as Infest hamsters, guinea pigs, rats and mice.
  • arthropods e.g. Cattle, sheep, goats, horses, pigs, donkeys, camels, buffalo, rabbits, chickens, turkeys, ducks, geese, bees, other pets such as e.g. Dogs, cats, house birds, aquarium fish and so-called experimental animals, such as Infest 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
  • implants through nasal Application, through 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 marks , Limb straps, holsters, marking devices etc.
  • active ingredients such as collars, ear tags, tail marks , 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 may be mentioned by way of example and preferably, but without limitation:
  • Termites like Kalotermes flavicollis, Cryptotermes brevis, Heterotermes indicola, Reticulitermes flavipes, Reticulitermes santonensis, Reticulitermes lucifugus, Mastotermes darwiniensis, Zootermopsis nevadensis, Coptotermes formosanus.
  • Bristle tails such as Lepisma saccharina.
  • non-living materials such as preferably plastics, adhesives, glues, papers and cartons, leather, wood, wood processing products and paints.
  • the one to be protected against insect attack is very particularly preferably
  • 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:
  • the active substances can be used as such, in the form of concentrates or generally customary formulations such as powders, granules, solutions, suspensions, emulsions or pastes.
  • the formulations mentioned can be prepared in a manner known per se, for example by mixing the active ingredients with at least one solvent or diluent, emulsifier, dispersant and / or binder or fixative, water repellants, optionally siccatives and UV stabilizers and added - if necessary dyes and pigments and other processing aids.
  • the insecticidal compositions or concentrates used to protect wood and wood-based materials contain the active compound 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, test gasoline 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. Te ⁇ entinöl and the like. For use.
  • the organic semi-volatile 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 also has an evaporation number above 35 and has 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 is replaced by an aliphatic polar organic chemical solvent or solvent mixture.
  • Aliphatic organic chemical solvents containing hydroxyl and / or ester and / or ether groups, such as, for example, glycol ethers, esters or the like, are preferably used.
  • the known organic-chemical binders are the water-dilutable 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 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
  • the synthetic resin used as a binder can be used in the form of an emulsion, dispersion or solution. Bitumen or bituminous nous substances up to 10 wt .-%, are used. 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 mentioned can be replaced by a fixing agent (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% 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, higher glycerol glycerol or glycerol ether - Kolether, glycerol ester and p-toluenesulfonic acid ester.
  • 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
  • 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 by industrial impregnation processes, e.g. vacuum, double vacuum or pressure processes.
  • the ready-to-use compositions can optionally contain further insecticides and, if appropriate, one or more fungicides.
  • insecticides and fungicides mentioned in WO 94/29 268 are preferably suitable as additional admixing partners.
  • the ones mentioned in this document are preferably suitable as additional admixing partners.
  • Insecticides such as chloropyriphos, phoxime, silafluofin, alphamethrin, cyfluthrin, cypermethrin, deltamethrin, permethrin, imidacloprid, NI-25, flufenoxuron, hexaflumuron, transfluthron, trifluoropuron, methifluoropuron, methifluoropuron, methifluoropuron
  • fungicides such as epoxyconazole, hexaconazole, azaconazole, propiconazole, tebuconazole, cyproconazole, metconazole, imazalil, dichlorofluoride, tolylfluanid, 3-iodo-2-propynylbutylcarbamate, N-octyl-isothiazolin-3-one and 4,5-dichloro -octyl-isothiazolin-3-one.
  • the compounds according to the invention can be used to protect objects, in particular ship hulls, sieves, nets, structures, quay systems and signaling systems which come into contact with sea or brackish water.
  • Baianus or pollicipes species increases the frictional resistance of ships and, as a result, leads to a significant increase in operating costs due to increased energy consumption and, moreover, frequent dry dock stays.
  • heavy metals such as e.g. in bis (trialkyltin) sulfides, tri-butyltin laurate, tri-rc-butyltin chloride, copper (I) oxide,
  • Triethyltin chloride tri - «- butyl (2-phenyl-4-chloro-phenoxy) -tin, tributyltin oxide, molybdenum disulfide, antimony oxide, polymeric butyl titanate, phenyl- (bispyridine) - bismuth chloride, tri-w-butylzirine fluoride, manganese ethylenebisto- dimethylcarbamate, zinc thiocarbamate, Zinc and copper salts of 2-pyridinthiol-1-oxide, bisdimethyldithiocarbamoylzinkethylenististhiocarbamate,
  • Zinc oxide, copper (I) ethylene bisdithiocarbamate, copper thiocyanate, copper phthalate and tributyltin halides can be omitted or the concentration of these compounds can be significantly reduced.
  • the ready-to-use antifouling paints can also be used if necessary
  • active ingredients preferably algicides, fungicides, herbicides, molluscicides or other antifouling active ingredients.
  • Suitable combination partners for the antifouling agents according to the invention are preferably:
  • thiophenecarboxylic acid cyclohexylamide-S, S-dioxide, dichlofluanid, fluorofolpet, 3-iodo-2-propynyl-butylcarbamate, tolylfluanid and azoles such as azaconazole, cyproconazole, epoxyconazole, hexaconazole, metconazole, propiconazole, propiconazole
  • the antifouling agents used contain the active compound according to the invention of the compounds according to the invention in a concentration of 0.001 to 50% by weight, in particular of 0.01 to 20% by weight.
  • the antifouling agents according to the invention further contain the usual ingredients such as e.g. in Ungerer, Chem. Ind. 1985, 37, 730-732 and Williams, Antifouling Marine Coatings, Noyes, Park Ridge, 1973.
  • antifouling paints contain in particular binders.
  • Examples of recognized binders are polyvinyl chloride in a solvent system, chlorinated rubber in a solvent system, acrylic resins in a solvent system, in particular in an aqueous system, vinyl chloride / vinyl acetate copolymer systems in the form of aqueous dispersions or in the form of organic solvent systems, butadiene / styrene / acrylonitrile rubbers, drying oils, such as linseed oil, resin esters or modified hard resins in combination with tar or bitumen, asphalt and epoxy compounds, small amounts of chlorinated rubber, chlorinated polypropylene and ninyl resins.
  • Paints may also contain inorganic pigments, organic pigments or dyes, which are preferably insoluble in sea water. Paints may also contain materials such as rosin to enable controlled release of the active ingredients. The paints may also contain plasticizers, modifiers that affect the rheological properties, and other conventional ingredients.
  • the self-compounds according to the invention or the abovementioned mixtures can also be incorporated into self-polishing antifouling systems.
  • the active ingredients are also suitable for controlling animal pests, in particular insects, arachnids and mites, which live in closed spaces such as apartments, factory halls, offices, vehicle cabins, etc. occurrence.
  • animal pests in particular insects, arachnids and mites, which live in closed spaces such as apartments, factory halls, offices, vehicle cabins, etc. occurrence.
  • insects in particular insects, arachnids and mites
  • they can be used alone or in combination with other active ingredients and auxiliaries in household insecticide products. They are effective against sensitive and resistant species and against all stages of development.
  • insects in particular insects, arachnids and mites, which live in closed spaces such as apartments, factory halls, offices, vehicle cabins, etc. occurrence.
  • auxiliaries in household insecticide products. They are effective against sensitive and resistant species and against all stages of development.
  • Sco ⁇ ionidea e.g. Buthus occitanus.
  • Acarina e.g. Argas persicus, Argas reflexus, Bryobia ssp., Dermanyssus gallinae, Glyciphagus domesticus, Ornithodorus moubat,
  • Opiliones e.g. Pseudosco ⁇ iones chelifer, Pseudosco ⁇ iones cheiridium, Opiliones phalangium.
  • Isopoda for example Oniscus asellus, Porcellio scaber.
  • Diplopoda for example, Blaniulus guttulatus, Polydesmus spp.
  • Lepismodes inquilinus From the order of the Blattaria e.g. Blatta orientalies, Blattella germanica, Blattella asahinai, Leucophaea maderae, Panchlora spp., Parcoblatta spp., Periplaneta australasiae, Periplaneta americana, Periplaneta brunnea, Periplaneta fuliginosa,
  • Saltatoria e.g. Acheta domesticus.
  • Dermaptera e.g. Forficula auricularia.
  • Lepidoptera e.g. Achroia grisella, Galleria mellonella, Plodia inte ⁇ unctella, Tinea cloacella, Tinea pellionella, Tineola bisselliella.
  • Ctenocephalides canis From the order of the Siphonaptera e.g. Ctenocephalides canis, Ctenocephalides felis, Pulex irritans, Tunga penetrans, Xenopsylla cheopis. From the order of the Hymenoptera e.g. Camponotus herculeanus, Lasius fuliginosus, Lasius niger, Lasius umbratus, Monomorium pharaonis, Paravespula spp., Tetramorium caespitum.
  • Rhodinus prolixus Triatoma infestans.
  • the application in the field of household insecticides is carried out alone or in combination with other suitable active ingredients such as phosphoric acid esters, carbamates, pyrethroids, growth regulators or active ingredients from other known classes of insecticides.
  • logP values specified in the tables and manufacturing examples above are determined in accordance with EEC Directive 79/831 Annex V.A8 by HPLC (High Performance Liquid Chromatography) on a phase reversal column (C 18). Temperature: 43 ° C.
  • the determination is carried out in the acidic range at pH 2.3 with 0.1% aqueous phosphoric acid and acetonitrile as eluents; linear gradient from 10% acetonitrile to 90% acetonitrile.
  • the calibration is carried out with unbranched alkan-2-ones (with 3 to 16 carbon atoms) whose logP values are known (determination of the logP values on the basis of the retention times by linear interpolation between two successive alkanones).
  • unbranched alkan-2-ones with 3 to 16 carbon atoms
  • logP values are known (determination of the logP values on the basis of the retention times by linear interpolation between two successive alkanones).
  • Solvent 7 parts by weight of dimethylformamide emulsifier: 2 parts 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 to the desired concentration with water containing emulsifier.
  • Pots filled with earth are poured with the active ingredient preparation. Immediately after the preparation, 5 corn kernels are laid out per pot and after 3 days the Diabrotica balteata larvae are placed on the treated soil. The concentration given relates to the amount of active ingredient per unit volume in the soil (mg / 1).
  • Active substances Active ingredient Degree of killing in% after 10 d m ppm
  • 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 to the desired concentration with water containing emulsifier.
  • Soybean shoots (Glycine max) are treated by dipping into the active ingredient preparation of the desired concentration and populated with Heliothis virescens caterpillars 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.
  • Emulsifier 2 parts 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 leaf beetle (Phaedon cochleariae) while the leaves are still moist.
  • the kill is determined in%. 100% means that all beetle larvae have been killed; 0% means that no beetle larvae have been killed.
  • 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 caterpillars of the cockroach (Plutella xylostella) 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.
  • 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 caterpillars of the army worm (Spodoptera exigua) 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.
  • 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 to the desired concentration with water containing emulsifier.
  • 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.
  • 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 to the desired concentration with water containing emulsifier.
  • Cotton plants (Gossypium hirsutum) are sprayed with an active ingredient preparation of the desired concentration. After the specified days, Heliothis virescens larvae are placed on the treated leaves in infection chambers.
  • the kill is determined in%. 100% means that all caterpillars have been killed; 0% means that no caterpillars have been killed.
  • Active substances Active ingredient Degree of killing concentration in% in ppm 7 d after infection
  • 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 to the desired concentration with water containing emulsifier.
  • Cotton plants (Gossypium hirsutum) are sprayed with an active ingredient preparation of the desired concentration. After the specified days, larvae of the army worm (Spodoptera frugiperda) are transferred to the treated in infection chambers
  • the kill is determined in%. 100% means that all caterpillars have been killed; 0% means that no caterpillars have been killed.
  • Active substances Active ingredient Degree of killing concentration in% in ppm 7 d after infection
  • Solvent 7 parts by weight of dimethylformamide emulsifier: 1 part by weight of alkylaryl polyglycol ether
  • Amount of emulsifier and dilute the concentrate with water to the desired concentration is required.
  • the active ingredient preparation is poured onto the floor.
  • the concentration of the active ingredient in the preparation is practically irrelevant, the only decisive factor is the amount of active ingredient per unit volume of soil, which is given in ppm (mg / 1). You fill the bottom in 0.25 1 pots and let them stand at 20 ° C.
  • Emulsifier 1 part by weight of alkylaryl polyglycol ether
  • Soybean shoots (Glycine max) of the Roundup Ready variety (trademark of Monsanto Comp. USA) are treated by dipping into the preparation of active compound of the desired concentration and are populated with the tobacco bud caterpillar Heliothis virescens 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.
  • Test animals Lucilia cuprina larvae
  • test tube containing approx. 1 cm 3 horse meat and 0.5 ml of the active ingredient preparation to be tested. The effectiveness of the active substance preparation is determined after 24 h and 48 h.
  • the test tubes are then transferred to beakers with a bottom covered with sand. After a further 2 days, the test tubes are removed and the dolls are counted.
  • the effect of the active substance preparation 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 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 kept in an air-conditioned room. The effects are checked after 7 days on the laying of fertile eggs. Eggs whose fertility is not externally visible are kept in glass tubes until larvae hatch in the climatic chamber. An effect of 100% means that no tick has laid fertile eggs.
  • Test animals adult Musca domestica, trunk Reichswald (OP, SP,
  • the effectiveness of the active ingredient preparation is determined. 100% means that all flies have been killed, 0% means that none of the flies have been killed.
  • Test animals Periplaneta americana solvent: dimethyl sulfoxide
  • test animals are immersed in the drug preparation to be tested for 1 minute. After being transferred to a plastic cup and stored for 7 days in an air-conditioned room, the degree of killing is determined. 100% means that all cockroaches have been killed, 0% means that none of the cockroaches have been killed.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

L'invention concerne de nouveaux dérivés de pyrazoline de formule (I), dans laquelle R<1>, R<2>, R<3> et R<4> ont les significations indiquées dans la description. Cette invention concerne également plusieurs procédés de production de ces substances et leur utilisation dans la lutte contre les parasites ainsi que de nouveaux produits intermédiaires et des procédés de production de ces derniers.
EP02758322A 2001-07-20 2002-07-08 Derives de pyrazoline et leur utilisation comme agents de lutte contre les parasites Withdrawn EP1412334A1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE10135551 2001-07-20
DE10135551A DE10135551A1 (de) 2001-07-20 2001-07-20 Pyrazolin-Derivate
PCT/EP2002/007569 WO2003010148A1 (fr) 2001-07-20 2002-07-08 Derives de pyrazoline et leur utilisation comme agents de lutte contre les parasites

Publications (1)

Publication Number Publication Date
EP1412334A1 true EP1412334A1 (fr) 2004-04-28

Family

ID=7692609

Family Applications (1)

Application Number Title Priority Date Filing Date
EP02758322A Withdrawn EP1412334A1 (fr) 2001-07-20 2002-07-08 Derives de pyrazoline et leur utilisation comme agents de lutte contre les parasites

Country Status (9)

Country Link
US (1) US20090143454A1 (fr)
EP (1) EP1412334A1 (fr)
JP (1) JP2005504748A (fr)
KR (1) KR20040022453A (fr)
CN (1) CN1271058C (fr)
BR (1) BR0211337A (fr)
DE (1) DE10135551A1 (fr)
MX (1) MXPA04000537A (fr)
WO (1) WO2003010148A1 (fr)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE10206791A1 (de) * 2002-02-19 2003-08-28 Bayer Cropscience Ag Substituierte 4-Pyrazolyl-pyrazoline
DE10257080A1 (de) * 2002-12-06 2004-06-24 Bayer Cropscience Ag Substituierte Pyrazolincarboxanilide
WO2007080430A1 (fr) * 2006-01-16 2007-07-19 Generics [Uk] Limited Nouveau procédé
US10743535B2 (en) 2017-08-18 2020-08-18 H&K Solutions Llc Insecticide for flight-capable pests
CN113679716B (zh) 2021-10-13 2024-03-26 史大永 溴酚-吡唑啉化合物在治疗猫冠状病毒疾病中的应用

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3991073A (en) * 1972-02-09 1976-11-09 U.S. Philips Corporation Pyrazoline compounds having insecticidal activity
US3992073A (en) * 1975-11-24 1976-11-16 Technical Wire Products, Inc. Multi-conductor probe
DE4032089A1 (de) * 1990-01-24 1991-07-25 Bayer Ag Substituierte pyrazolinderivate
DE4117076A1 (de) * 1991-05-25 1992-11-26 Bayer Ag Substituierte 4-hetaryl-pyrazoline
DE4141187A1 (de) * 1991-12-13 1993-06-17 Bayer Ag Verfahren zur herstellung von substituierten pyrazolinen
US5338856A (en) * 1992-08-17 1994-08-16 Dowelanco 3,4-N,trisubstituted-4,5-dihydro-1H-pyrazole-1-carboxamides and their use as insecticides
DE4336307A1 (de) * 1993-10-25 1995-04-27 Bayer Ag Substituiertes Pyrazolinderivat
DE4416112A1 (de) * 1994-05-06 1995-11-09 Bayer Ag Substituierte Tetrahydropyrazole

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO03010148A1 *

Also Published As

Publication number Publication date
US20090143454A1 (en) 2009-06-04
KR20040022453A (ko) 2004-03-12
MXPA04000537A (es) 2004-07-07
JP2005504748A (ja) 2005-02-17
BR0211337A (pt) 2004-09-28
DE10135551A1 (de) 2003-01-30
CN1555363A (zh) 2004-12-15
WO2003010148A1 (fr) 2003-02-06
CN1271058C (zh) 2006-08-23

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