EP0789683A1 - Esters de fluorobutenyle et leur utilisation pour combattre les parasites animaux - Google Patents

Esters de fluorobutenyle et leur utilisation pour combattre les parasites animaux

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Publication number
EP0789683A1
EP0789683A1 EP95937045A EP95937045A EP0789683A1 EP 0789683 A1 EP0789683 A1 EP 0789683A1 EP 95937045 A EP95937045 A EP 95937045A EP 95937045 A EP95937045 A EP 95937045A EP 0789683 A1 EP0789683 A1 EP 0789683A1
Authority
EP
European Patent Office
Prior art keywords
formula
spp
alkyl
compounds
optionally
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP95937045A
Other languages
German (de)
English (en)
Inventor
Udo Kraatz
Jürgen Hartwig
Wolfram Andersch
Christoph Erdelen
Andreas Turberg
Norbert Mencke
Gopichand Yalamanchili
Peter Gerrard Ruminski
Dennis Paul Phillion
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Bayer AG
Monsanto Co
Original Assignee
Bayer AG
Monsanto Co
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Filing date
Publication date
Application filed by Bayer AG, Monsanto Co filed Critical Bayer AG
Publication of EP0789683A1 publication Critical patent/EP0789683A1/fr
Withdrawn legal-status Critical Current

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Classifications

    • 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
    • A01N47/02—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 no bond to a nitrogen atom
    • A01N47/06—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 no bond to a nitrogen atom containing —O—CO—O— groups; Thio analogues thereof
    • 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
    • A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
    • A01N47/12—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing a —O—CO—N< group, or a thio analogue thereof, neither directly attached to a ring nor the nitrogen atom being a member of a heterocyclic ring
    • 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
    • A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
    • A01N47/16—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof the nitrogen atom being part of a heterocyclic ring
    • 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
    • A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
    • A01N47/20—N-Aryl derivatives thereof
    • 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
    • A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
    • A01N47/24—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing the groups, or; Thio analogues thereof
    • 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
    • C07C271/06—Esters of carbamic acids
    • C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
    • C07C271/10—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C271/12—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
    • 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
    • C07C271/06—Esters of carbamic acids
    • C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
    • C07C271/10—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C271/14—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of hydrocarbon radicals substituted by halogen atoms or by nitro or nitroso groups
    • 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
    • C07C271/06—Esters of carbamic acids
    • C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
    • C07C271/24—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atom of at least one of the carbamate groups bound to a carbon atom of a ring other than a six-membered aromatic ring
    • 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
    • C07C271/06—Esters of carbamic acids
    • C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
    • C07C271/26—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atom of at least one of the carbamate groups bound to a carbon atom of a six-membered aromatic ring
    • C07C271/28—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atom of at least one of the carbamate groups bound to a carbon atom of a six-membered aromatic ring to a carbon atom of a non-condensed six-membered aromatic ring
    • 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
    • C07C271/62—Compounds containing any of the groups, X being a hetero atom, Y being any atom, e.g. N-acylcarbamates
    • C07C271/66—Y being a hetero atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
    • C07C311/50—Compounds containing any of the groups, X being a hetero atom, Y being any atom
    • C07C311/52—Y being a hetero atom
    • C07C311/53—X and Y not being nitrogen atoms, e.g. N-sulfonylcarbamic acid
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C329/00—Thiocarbonic acids; Halides, esters or anhydrides thereof
    • C07C329/02—Monothiocarbonic acids; Derivatives thereof
    • C07C329/04—Esters of monothiocarbonic acids
    • C07C329/06—Esters of monothiocarbonic acids having sulfur atoms of thiocarbonic groups bound to acyclic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/96—Esters of carbonic or haloformic acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
    • C07D295/18—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
    • C07D295/182—Radicals derived from carboxylic acids
    • C07D295/185—Radicals derived from carboxylic acids from aliphatic carboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
    • C07D295/20—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carbonic acid, or sulfur or nitrogen analogues thereof
    • C07D295/205—Radicals derived from carbonic acid
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/14—The ring being saturated

Definitions

  • the present invention relates to new fluorobutenyl esters, ner processes for their production and their use for controlling animal pests, in particular insects, arachnids and ⁇ ematodes, which protect in agriculture, in forests, in the norrate and material and in the hygiene sector.
  • R 1 represents hydrogen or halogen
  • R for one of groups (a) or (b)
  • Y represents oxygen or sulfur
  • Z represents oxygen, sulfur or ⁇ R 4 ,
  • R stands for hydrogen or for optionally substituted alkyl, alkenyl, cycloalkyl, aryl, aralkyl, alkoxycarbonyl, aryloxycarbonyl, arylsulfonyl or hetaryl and
  • R 4 stands for hydrogen or for optionally substituted alkyl, alkylthio, alkenyl, cycloalkyl, aryl, aralkyl or hetaryl or
  • R 3 and R 4 together with the nitrogen atom to which they are attached form an optionally substituted ring which optionally contains oxygen, sulfur or nitrogen (which is optionally substituted by alkyl, aryl or aralkyl),
  • N stands for oxygen or ⁇ R 6 and
  • R 5 and R 6 independently of one another represent hydrogen, an aliphatic group with one to twelve carbon atoms, an aromatic or heterocyclic group, each optionally substituted by at least one substituent from the series alkyl, cyano,
  • R 7 and R 8 independently of one another represent hydrogen, alkyl or aryl
  • R 9 represents hydrogen, alkyl, haloalkyl or aryl
  • R 10 and R 11 independently of one another are hydrogen, alkyl, aryl, alkoxy,
  • the compounds of the formula (I) can exist as geometric and / or optical isomers or isomer mixtures of different compositions.
  • the invention relates to both the pure isomers and the isomer mixtures.
  • Those compounds of formula (I) which have a carboxyl or a hydroxyl group can be used as salts in combination with different cations, e.g. Alkali metals or alkaline earth metals such as sodium, potassium, calcium, magnesium or quaternary ammonium ions such as the isopropylammonium ion or the
  • CF 2 CR 1 -CH 2 -CH 2 -SCVR 5
  • R, ⁇ , R, R, V, Y and Z have the meaning given above.
  • R 1 has the meaning given above
  • R 1 has the meaning given above
  • CF 2 C- -CH; -CH, - O— C-Cl (N)
  • R 1 and Y have the meanings given above,
  • R 1 and Y have the meanings given above,
  • the compounds of the formula (Ic) can be prepared with the aid of known methods from compounds which are known and some of which are commercially available, or which are simple to prepare by known methods (cf. the preparation examples).
  • the new compounds of the formula (I) have highly pronounced biological properties and, above all, for combating animal pests, in particular insects, arachnids and nematodes, which are used in agriculture, in forests, in stocks and materials protection as well as in the hygiene sector.
  • the compounds according to the invention are generally defined by the formula (I).
  • R 1 preferably represents hydrogen, fluorine or chlorine.
  • R 2 preferably represents one of the groups
  • Y represents oxygen or sulfur
  • Z represents oxygen, sulfur or NR 4 , R 3 for hydrogen
  • Alkanediyl single or double, identical or different by C, -C 8 alkyl, C, -C 8 haloalkyl, C r C 8 alkoxy, C 3 -C 8 cycloalkyl, C 3 -C 8 halocycloalkyl, C j - j -Alkyl ⁇ -Cg-cycloalkyl, in each case optionally by halogen, cyano, nitro, C j -C 8 -alkyl, C j -C 8 -haloalkyl, C, -C 8 -alkoxy, C r C 8- haloalkoxy, C, -C 8 -alkylthio or C r C 8 -haloalkylthio substituted phenyl or benzyl is substituted) substituted C r C ] 0 -alkyl,
  • C j -C 6 -alkoxy-substituted C - C is 8 alkoxycarbonyl.
  • R 4 preferably represents hydrogen
  • halogen for optionally by halogen, cyano, amino (which is optionally substituted by C -, - C 7 -alkanediyl or optionally monosubstituted or disubstituted, identically or differently by C r C 8 -alkyl), C, -C 8 -alkoxy, C ⁇ C 8 - alkylthio, aminocarbonyl (which is optionally substituted by C 2 -C 7 alkanediyl, one to two times, identical or different by C, -C 8 alkyl, C ⁇ C 8 - Haloalkyl, C 3 -C 8 cycloalkyl, C 3 -C 8 halocycloalkyl, C, -C 4 alkyl- C 3 -C 8 cycloalkyl, each optionally by halogen, cyano, nitro, C r C 8 alkyl , C r C 8 haloalkyl, C r C 8 alkoxy,
  • R 3 and R 4 together with the nitrogen atom to which they are attached form a 4- to 8-membered ring which is optionally substituted by C r C 8 alkyl and which optionally contains oxygen, sulfur or nitrogen (more if appropriate is substituted by C j -C 8 alkyl, phenyl or benzyl) contains.
  • R 1 particularly preferably represents fluorine.
  • R 2 particularly preferably represents the group
  • Z represents oxygen, sulfur or NR 4 ,
  • R 4 particularly preferably represents hydrogen
  • R 3 and R 4 together with the nitrogen atom to which they are attached form a 4- to 8-membered ring, optionally substituted by C 1 -C 8 -alkyl, which optionally contains oxygen, sulfur or nitrogen (which if appropriate is substituted by C j -Cg alkyl, phenyl or benzyl) contains.
  • R 1 very particularly preferably represents fluorine.
  • R 2 very particularly preferably represents the group
  • Z represents oxygen, sulfur or NR 4 ,
  • R 4 very particularly preferably represents hydrogen, C, -C 4 alkyl, which is optionally substituted by fluorine or chlorine .substitutechnisches C r C 3 alkylthio or C 4 -C 6 cycloalkyl
  • R 3 and R 4 form together with the nitrogen atom to which they are attached membered 8-a 4- to, substi- tuted optionally substituted by C j -C ⁇ alkyl ring which may contain oxygen, sulfur or nitrogen (wel ⁇ cher optionally is substituted by C ] -C 4 alkyl or benzyl).
  • a further preferred group of compounds are compounds of the formula (Ic), in particular those in which Z represents oxygen and R 5 represents an aliphatic group, preferably lower alkyl, in particular ethyl.
  • R 5 represents an aliphatic group, preferably lower alkyl, in particular ethyl.
  • hydrocarbon radicals such as alkyl or alkenyl - also in connection with heteroatoms such as alkoxy or alkylthio - are in each case straight-chain or branched as far as possible.
  • halogen means fluorine, chlorine, bromine, iodine.
  • alkyl stands for straight-chain or branched C, -C 7 alkyl.
  • lower alkyl stands for straight-chain or branched C 1 -C 4 -alkyl.
  • aliphatic stands for saturated or unsaturated, straight-chain or branched alkyl having one to ten carbon atoms (or as indicated) or for straight-chain or branched alkenyl with two to ten carbon atoms (or as indicated).
  • alkoxy stands for lower alkyl bonded via an oxygen atom.
  • alkylthio stands for lower alkyl bonded via a sulfur atom.
  • alkoxycarbonyl stands for a lower alkyl ester of a carboxyl group.
  • amino acid means that NR 5 R 6 is the optionally substituted amino group of a natural or non-naturally occurring amino acid.
  • heterocyclic group means any cyclic group that contains at least one element other than carbon in the ring.
  • the heteroatom can be oxygen, nitrogen, sulfur or another element.
  • heterocycles are: thiadiazole, pyridine, thiazole, isothiazole, oxazole, imidazole, pyrazole, triazole, benzothiazole, sulfur-containing heterocycles, morpholine, piperidine, piperazine or pyrrolidine, which are optionally substituted by at least one radical from the cyano series , Trimethylsilyl, hydroxy, alkoxy, halogen, nitro, amino, SH, alkylthio, carboxy, alkoxycarbonyl, phenyl, the rest of a carboxylic acid, sulfonic acid, phosphonic acid or phosphinic acid or an ester, thioester or an amide of these acids.
  • CF 2 CF-CH -CH - OH - + - CI-C-OC 2 H 5 - ⁇
  • CF 2 CF -CH-CH 2 -0-C -OC 2 H 5
  • CF 2 CF-CH 2 -CH— SH -h CI-CS-CH
  • CF 2 CF-CH-CH - S-CS-CH 3
  • CF 2 CF-CH 2 -CH - O - C 11 - Cl - H 2 N— / ( ⁇ )
  • CF 2 CF-CH-CH - S - C - Cl + HN r O
  • CF, CF-CH, -CH— S— CN O 2 2 ⁇ /
  • Halogenated aliphatic or aromatic hydrocarbons, ethers or nitriles such as e.g. Cyclohexane, toluene, chlorobenzene, chloroform, dichloromethane, dichloroethane, dioxane, tetrahydrofuran, diethyl ether or acetonitrile.
  • Alkali or alkaline earth metal hydroxides, alkali or alkaline earth metal carbonates or hydrogen carbonates or nitrogen bases are preferably usable. Examples include sodium hydroxide, calcium hydroxide, potassium carbonate, sodium hydrogen carbonate, triethylamine, dibenzylamine, diisopropylamine, pyridine, quinoline, diazabicyclooctane (DABCO), diazabicyclononene (DBN) and diazabicycloundecene (DBU).
  • DABCO diazabicyclooctane
  • DBN diazabicyclononene
  • DBU diazabicycloundecene
  • the process Aß described above for the preparation of the compounds of the formula (I) is characterized in that the reaction is carried out, if appropriate, in the presence of a catalyst.
  • Diazabicyclooctane (DABCO) triethylamine or pyridine or organic tin compounds such as, for example, dibutyltin dilaurate can be used as the catalyst.
  • reaction temperatures in the processes A ⁇ , Aß, B, C and D described above can each be varied within a substantial range.
  • a ⁇ , B, C and D are generally carried out at temperatures between -10 ° C and 150 ° C, preferably between 0 ° C and 90 ° C.
  • the Aß process is generally carried out at temperatures between 0 ° C. and 120 ° C., preferably between 20 ° C. and 100 ° C.
  • the ratio of the starting materials of the formulas (II) and (III) in process A ⁇ or of the formulas (Ila) and (III) in process B is generally 1: 1 to 2: 1.
  • the ratio of the starting materials of the formulas (II) and (IV) in the process Aß is generally between 2: 1 and 1: 2, preferably equivalent amounts are used.
  • the ratio of the starting materials of the formulas (V) and (NI) in ner driving C or the formulas (Nil) and (NIII) in ner driving D is generally between 1: 1 and 10: 1.
  • the above-described ner processes A ⁇ , Aß, B, C and D are generally carried out under normal pressure.
  • the reaction mixture is, for example, diluted with water, extracted with an organic solvent and the organic phase is concentrated.
  • the starting materials of the formula (II) used in the production processes A ⁇ and Aß are known and can be prepared by known methods (see, for example, WO 92/15 555).
  • the starting materials of the formula (III) or (purple) which are further used in the production process A ⁇ and B are known and / or can be prepared according to known methods
  • the compounds of the formula (III) or (purple) are obtained, for example, if alcohols, thiols or amines of the formula (VI) in implemented in a known manner and phosgene or thiophosgene (see, for example, Houben-Weyl, Methods of Organic Chemistry, Volume E 4, pp. 407 ff, Georg Thieme Verlag Stuttgart, New York, 1983).
  • the ⁇ so (thio) cyanates of the formula (IV) used as starting materials in the production process Aß are generally known synthetic chemicals of organic chemistry.
  • the starting materials of the formula (V) used in production process C are new, but can be prepared by known methods.
  • the compounds of the formula (V) are obtained, for example, if compounds of the formula (II) are reacted with phosgene or thiophosgene in a manner known per se (see above).
  • the starting materials of the formula (VI) which are also used in production process C are generally known synthetic chemicals of organic chemistry.
  • the starting materials of the formula (VII) used in production process D are new, but can be prepared by known methods. You get that
  • the starting materials of the formula (VIII) which are also used in production process D are generally known compounds of organic chemistry.
  • the active substances are suitable for controlling animal pests, in particular insects, arachnids and nematodes, which protect in agriculture, in forests, in the supply and material and in the hygiene sector. They can preferably be used as pesticides. They are effective against normally sensitive and resistant species and against all or individual stages of development.
  • the pests mentioned above include:
  • Diplopoda for example, Blaniulus guttulatus.
  • Chilopoda for example, Geophilus carpophagus and Scutigera spec.
  • Thysanura e.g. Lepisma saccharina.
  • Thysanoptera e.g. Hercinothrips femoralis, Thrips tabaci.
  • 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 sppe, Phros
  • Empoasca spp. Euscelis bilobatus, Nephotettix cincticeps, Lecanium corni, Saissetia oleae, Laodelphax striatellus, Nilaparvata lugens, Aonidiella aurantii, Aspidiotus hederae, Pseudococcus spp., Psylla spp.
  • Cheimatobia brumata Lithocolletis blancardella, Hyponomeuta padella, Plutella maculipennis, Malacosoma neustria, Euproctis chrysorrhoea, Lymantria spp., Bucculatrix thurberiella, Phyllocnisüs citrella, Agrotis spp., Euxoa spp., Feltia spp., Earias insulana, Heliothis spp., Spodoptera exigua, Mamestra brassicae, Panolis flammea, Spodoptera litura, Spodoptera spp., Trichoplellaocapsi.
  • Cacoecia podana Capua reticulana, Choristoneura fumiferana, Clysia ambiguella, Homona magnanima, Tortrix viridana.
  • Hymenoptera e.g. Diprion spp., Hoplocampa spp., Lasius spp., Monomorium pharaonis, Vespa 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., Tabanus spp.
  • Tannia spp. Bibio hortulanus, Oscinella frit, Phorbia spp., Pegomyia hyoscyami, Ceratitis capitata, 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., Sarcoptes 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.,
  • the compounds of the formula (I) according to the invention are notable in particular for outstanding insecticidal and nematicidal activity.
  • leaf and soil insects When used against leaf and soil insects, they show strong effects, for example against horseradish leaf beetle larvae (Phaedon cochleariae) and caterpillars of the cabbage cockroach (Plutella maculipennis).
  • nematodes When used against nematodes, they show strong effects, for example against Meloidogyne incognita.
  • the active compounds according to the invention show not only protective, but also leaf-systemic and root-systemic properties.
  • the active compounds of the formula (I) according to the invention also have a fungicidal action, for example against Pyricularia oryzea on rice.
  • 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 as well as very fine encapsulations in polymers
  • 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, optionally using surface-active agents, that is to say emulsifiers and / or dispersants and / or foam-generating agents.
  • extenders that is to say liquid solvents and / or solid carriers
  • 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.
  • aromatics such as xylene, toluene, or alkylnaphthalenes
  • chlorinated aromatics and chlorinated aliphatic hydrocarbons.
  • Substances such as chlorobenzenes, chlorethylenes or methylene chloride, aliphatic hydrocarbons such as cyclohexane or paraffins, for example petroleum fractions, mineral and vegetable oils, alcohols such as butanol or glycol and their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone , strongly polar solvents such as dimethylformamide and. Dimethyl sulfoxide and water.
  • 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 stone powder, such as highly disperse silica, aluminum oxide and
  • Silicates as solid carriers for granules are possible: 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; come in as emulsifying and / or foaming agents
  • nonionic 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 polymers in the form of powders, granules or latices, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, and natural phospholipids such as cephalins and lecithins and synthetic phospholipids can be used in the formulations.
  • Other additives can be mineral and vegetable oils.
  • Dyes such as inorganic pigments, e.g. Iron oxide, titanium oxide,
  • Ferrocyan blue and organic dyes such as alizarin, azo and metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc are used.
  • the formulations generally contain between 0J and 95% by weight of active compound, preferably between 0.5 and 90%.
  • the active substance according to the invention can be used in its commercially available formulations and in the use forms prepared from these formulations Mixture with other active ingredients, such as insecticides, attractants, sterilants, bactericides, acaricides, nematicides, fungicides, growth-regulating substances or herbicides.
  • active ingredients such as insecticides, attractants, sterilants, bactericides, acaricides, nematicides, fungicides, growth-regulating substances or herbicides.
  • the insecticides include, for example, phosphoric acid esters, carbamates, carboxylic acid esters, chlorinated hydrocarbons, phenylureas, substances produced by microorganisms and others
  • Difenoconazol Dimethirimol, Dimethomorph, Diniconazol, Dinocap, Diphenylamine, Dipyrithion, Ditalimfos, Dithianon, Dodine, Drazoxolon, Edifenphos, Epoxyconazole, Ethirimol, Etridiazole, Fenarimol, Fenbuconicitropene, Fenanpropylphenol, Fenfurampidon, Fenfurampidol, Fenfurampidon, Fenfurampidol, Fenfurampidol, Fenfurampidol, Fenfurampidon, Fenfurampidol, Fenfurampidol, Fenfurampidol, Fenfurampidol, Fenfurampid Fentin Hydroxyd, Ferbam, Ferimzone, Fluazinam, Fluioxonil, Fluoromide, Fluquinconazole, Flusilazole, Flusulfamide, Flutolanil
  • copper preparations such as: copper hydroxide, copper naphthenate, copper oxychloride, copper sulfate, copper oxide, oxine copper and Bordeaux mixture, Mancopper, Mancozeb, Maneb, Mepanipyrim, Mepronil, Metalaxyl, Metconazole, Methasulfocarb, Methfuroxam, Metaxam, Metiram, Mets Myclobutanil, Nickel dimethyldithiocarbamate, nitrothal isopropyl, Nuarimol, Ofurace, Oxadixyl, Oxamocarb, Oxycarboxin,
  • PCNB Quintozen
  • Tebuconazole Tebuconazole, tecloftalam, tecnazen, tetraconazole, thiabendazole, thicyofen, thiophanate-methyl, thiram, tolclophos-methyl, tolylfluanid, triadimefon, triadimenol, triazoxide, trichlamide, tricyclazole, tridemoizol, trifi forumol, trififorumol, trififorumol, trififorumol
  • Bactericides bronopol, dichlorophene, nitrapyrin, nickel-dimethyldithiocarbamate, kasugamycin, octhilinone, furan carboxylic acid, oxytetracycline, probenazole, streptomycin, tecloftalam, copper sulfate and other copper preparations.
  • Imidacloprid Iprobefos, Isazophos, Isofenphos, Isoprocarb, Isoxathion, Ivermectin, Lambda-cyhalothrin, Lufenuron,
  • Parathion A Parathion M, Permethrin, Phenthoat, Phorat, Phosalon, Phosmet,
  • the active compounds according to the invention can furthermore be present in their commercially available formulations and in the use forms prepared from these formulations in conjunction 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 contains the application forms prepared from the commercially available formulations can vary within wide ranges.
  • the drug concentration can be from 0.0000001 to 95% by weight of active compound, preferably between 0.0001 and 1% by weight.
  • the application takes place in a customary manner adapted to the application forms.
  • Active ingredient characterized by an excellent residual effect on wood and clay as well as a good alkali stability 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.
  • Anoplurida e.g. Haematopinus spp., Linognathus spp., Pediculus spp., Phtirus spp., Solenopotes spp ..
  • 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., Braula spp., Musca spp., Hydrotaea spp., Stomoxys spp., Haematobia spp., Morellia spp., Fannia spp., Glossina spp., Calliphora spp., Glossina spp., Calliphora spp., Glossina spp.,
  • Siphonaptrida for example Pulex spp., Ctenocephalides spp., Xenopsylla spp., Ceratophyllus spp ..
  • the Heteropterida for example Cimex spp., Triatoma spp., Rhodnius spp., Panstrongylus spp ..
  • Mesostigmata e.g. Argas spp., Ornithodorus spp., Otabius spp., Ixodes spp., Amblyomma spp., Boophilus spp., Dermacentor spp., Haemaphysalis spp., Hyalomma spp., Rhipicephalus spp., Dermanyssus spp., Raillneu- spp., Pill monyssus spp., Sternostoma spp., Varroa spp ..
  • Actinedida Prostigmata
  • Acaridida e.g. 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 controlling arthropods which are used in agricultural animals, such as e.g. Cattle, sheep, goats, horses, pigs, donkeys, camels, buffalos, rabbits, chickens, turkeys, ducks,
  • Geese bees, other pets such as Dogs, cats, house birds, aquarium fish and so-called experimental animals such as Infest hamsters, guinea pigs, rats and mice.
  • 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, such as Example by injections (intramuscular, subcutaneous, intravenous, intraperitoneal, etc.), implant by nasal 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 bands, holsters, marking devices, etc.
  • enteral administration in the form of, for example, tablets, capsules, drinkers, drenches, granules, pastes, boluses, the feed-through method, suppositories
  • parenteral administration such as Example by injection
  • 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:
  • Kalotermes flavicollis Cryptotermes brevis, Heterotermes indicola, Reticulitermes flavipes, Reticulitermes santonensis, Reticulitermes lucifugus, Mastotermes darwinisis, Zootermopsis nevadensis, Coptotermes formosanus.
  • Bristle tails such as Lepisma saccharina.
  • 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.
  • 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, jetties, wooden vehicles, boxes, pallets, containers, telephone masts, wooden cladding, wooden windows and doors , Plywood, chipboard, carpentry or wood products that are used in general in house construction or in carpentry.
  • 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.
  • the formulations mentioned can be prepared in a manner known per se, e.g. by mixing the active ingredients with at least one solvent or diluent, emulsifier, dispersant and / or binder or fixative, water repellant, optionally siccatives and UV stabilizers and, where appropriate, dyes and pigments and further processing aids.
  • the insecticidal compositions or concentrates used to protect wood and wood-based materials 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 ingredient, based on the material to be protected
  • An organic chemical solvent or solvent mixture and / or an oily or oily heavy serves as the solvent and / or diluent volatile 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 agent.
  • 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 solvents, 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 are advantageous ° C, Te ⁇ entinöl and the like. For use.
  • organic low-volatility oily or oily solvents with a vaporization 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 likewise has a vaporization 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 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-thinnable 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 an 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 .
  • the synthetic resin used as a binder can be used in the form of an emulsion, dispersion or solution. Bitumen or bituminous substances of 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 organic chemical binder.
  • binder All or part of the binder mentioned can be replaced by a fixative (mixture) or a plasticizer (mixture) .
  • a fixative mixture
  • a plasticizer mixture
  • 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 or high molecular weight glycerol, glycerol - Kolether, glycerol ester and p-toluenesulfonic acid ester
  • Fixing agents are chemically based on polyvinyl alkyl ethers such as polyvinyl methyl ether or ketones such as benzophenone and 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 pressure process.
  • 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 compounds mentioned in this document are an integral part of the present application.
  • Insecticides such as chloropyriphos, phoxi, silafluofin, alphamethrin, cyfluthrin, cypermethrin, delta-methrin, permethrin, imidacloprid, NI-25, flufenoxuron, hexaflumuron and triflumuron, as well as fungazazole, as well as fungazizides, such as epizazole, as well as fungazizides such as Azaconazole, propiconazole, tebuconazole, cyproconazole, metconazole, imazalil, dichlorfluanid, tolylfluanid, 3-iodo-2-propynylbutylcarbamate, N-octyl-isothiazolin-3-one and 4,5-dichloro-N-octylisothiazolin-3-one, his.
  • CF 2 CF-CH 2 -CH 2 -O-CO-OC 2 H 5 (1-1)
  • CF 2 CF-CH 2 -CH 2 -SC - NH-CH 2 -COOCH 3
  • the compound is prepared analogously to Example 1-38, with an equivalent amount of glycine tert-butyl ester hydrochloride being used instead of glycine methyl ester hydrochloride.
  • This compound is prepared analogously to Example 1-38, glycine methyl ester hydrochloride being replaced by an equivalent amount of ⁇ -methylglycine tert-butyl ester hydrochloride.
  • CF 2 CF-CH 2 -CH 2 -SC - NH-CH 2 -CH 2 -CN
  • Test nematode Meloidogyne incognita solvent: 4 parts by weight of acetone
  • 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, the stated amount of emulsifier is added and the concentrate is diluted with water to the desired concentration.
  • the active ingredient preparation is intimately mixed with the soil that is heavily contaminated with the test nematodes.
  • the lettuce roots are examined for nematode infestation (root galls) and the efficiency of the active ingredient is determined in%.
  • the degree of efficiency is 100% if the infestation is completely avoided, it is 0% if the infestation is just as high as that of the control plants in untreated but contaminated soil in the same way.
  • 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 stated 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 with horseradish leaf beetle larvae
  • the kill is determined in%. 100% means that all beetle larvae have been killed; 0% means that no beetle larvae have been killed.
  • the Nerbinding according to Production Example 1-6 at an exemplary active ingredient concentration of 0.1% caused 100% to be killed after 7 days.
  • 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 amount of solvent and the stated 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 cabbage cockroach (Plutella maculipennis) 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 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 owl butterfly (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 amount of solvent and the stated amount of emulsifier, and the concentrate is diluted with water to the desired concentration.
  • Rice seedlings (Oryza sativa) are treated by dipping into the active ingredient preparation of the desired concentration and populated with the green rice leafhopper (Nephotettix cincticeps) while the seedlings are still moist.
  • the kill is determined in%. 100% means that all cicadas have been killed; 0% means that no cicadas have been killed.
  • Test animals adult sucked females
  • Solvent 35 parts by weight of ethylene glycol monomethyl ether.
  • Emulsifier 35 parts by weight of nonylphenol polyglycol ether
  • Solvent 35 parts by weight of ethylene glycol monomethyl ether.
  • Emulsifier 35 parts by weight of nonylphenol polyglycol ether
  • test tubes About 20 Lucilia cuprina larvae are placed in a 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 and 48 hours.
  • the test tubes are 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 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.

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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)
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  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

Des esters de fluorobutényle ont la formule (I), dans laquelle R1 désigne hydrogène ou un halogène et R2 désigne un des groupes (a), (b) ou (c), dans lesquels V, Y, Z, R3 et R5 ont la notation donnée dans la description. L'invention concerne également leur procédé de préparation et des produits intermédiaires, ainsi que leur utilisation pour combattre les parasites animaux.
EP95937045A 1994-11-04 1995-11-02 Esters de fluorobutenyle et leur utilisation pour combattre les parasites animaux Withdrawn EP0789683A1 (fr)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
DE4439335A DE4439335A1 (de) 1994-11-04 1994-11-04 Kohlensäure- und Carbamidsäurefluorbutenylester
DE4439335 1994-11-04
US398795P 1995-10-06 1995-10-06
US39878 1995-10-06
PCT/EP1995/004298 WO1996014289A1 (fr) 1994-11-04 1995-11-02 Esters de fluorobutenyle et leur utilisation pour combattre les parasites animaux

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EP0789683A1 true EP0789683A1 (fr) 1997-08-20

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CA (1) CA2204241A1 (fr)
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US5866711A (en) * 1996-09-13 1999-02-02 E. I. Du Pont De Nemours And Company Fluorocyanate and fluorocarbamate monomers and polymers thereof
JPWO2004108662A1 (ja) * 2003-05-15 2006-07-20 クミアイ化学工業株式会社 フェニルスルホニルカーバメイト誘導体及び農園芸用植物病害防除剤
KR102555589B1 (ko) * 2021-09-24 2023-07-13 컨템포러리 엠퍼렉스 테크놀로지 씨오., 리미티드 바인더 화합물, 도전성 바인더 및 이를 포함하는 이차 전지

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US3689662A (en) * 1970-12-10 1972-09-05 Wayne C Jaeschke Nematocidel use of 3,4,4-trifluoro-3-butenylthio methylidene compounds
US4748186A (en) * 1986-06-30 1988-05-31 Fmc Corporation S-trifluorobutenyl derivatives and pesticidal uses thereof

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JPH10508592A (ja) 1998-08-25
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BR9509592A (pt) 1997-09-30
CA2204241A1 (fr) 1996-05-17
AU3927195A (en) 1996-05-31
DE4439335A1 (de) 1996-05-09
WO1996014289A1 (fr) 1996-05-17
NO971767L (no) 1997-04-17
FI971863A (fi) 1997-04-30
FI971863A0 (fi) 1997-04-30
MX9703193A (es) 1997-11-29
HUT77297A (hu) 1998-03-30

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