Classifications

• • 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
  • C07D231/06—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
• • 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

Definitions

• the present application of an invention relates to the use of known and new pyrazolinols and their derivatives as plant treatment agents, in particular for controlling animal pests, plant treatment agents based on known and new pyrazolinols and their derivatives, and new trifluoromethyl-pyrazolinols and their derivatives and processes for their manufacture.
• A represents optionally substituted alkyl
• Q represents oxygen or sulfur
• R 1 represents hydrogen or optionally substituted alkyl, alkylcarbonyl, alkenyl,
• R 2 represents hydrogen or represents optionally substituted alkyl, alkylcarbonyl, alkoxycarbonyl, cycloalkyl, aryl, arylalkyl or heterocyclyl,
• R 3 stands for optionally substituted alkyl, alkenyl, cycloalkyl, aryl, arylalkyl or heterocyclyl, R 2 and R 3 also together represent alkanediyl (alkylene),
• R 4 stands for hydrogen, for amino, or for optionally substituted alkyl, alkylcarbonyl, alkylsulfonyl, alkylamino, alkylcarbonylamino, alkylsulfonylamino, alkenyl, alkenylcarbonyl or alkynyl, and
• R 5 stands for hydrogen or for optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, aryl, arylalkyl, heterocyclyl or heterocyclylalkyl, have strong activity against animal pests.
• Saturated or unsaturated hydrocarbon radicals such as alkyl or alkenyl
• alkyl or alkenyl are in each case straight-chain or branched as far as possible, also in conjunction with heteroatoms, such as in alkoxy.
• Optionally substituted radicals can be mono- or polysubstituted, whereby in the case of multiple substitution the substituents can be the same or different.
• the compounds of the general formula (I) according to the invention contain at least one asymmetrically freshly substituted carbon atom and can therefore exist in various enantiomeric (R- and S-configured forms) or diastereomeric forms.
• the invention relates both to the use of the various possible individual enantiomeric or stereoisomeric forms of the compounds of the general formula (T) and to the mixtures of these isomeric compounds.
• A preferably represents optionally by hydroxy, cyano, halogen, CC 4 alkoxy or
• C haloalkoxy substituted C r C 8 alkyl is C haloalkoxy substituted C r C 8 alkyl.
• A particularly preferably represents in each case optionally by hydroxy, cyano, fluorine, chlorine,
• Bromine methoxy, ethoxy, n- or iso-propoxy, monofluoromethoxy, difluoromethoxy, trifluoromethoxy, monofluoroethoxy, difluoroethoxy or trifluoroethoxy substituted methyl, ethyl, n- or iso-propyl, n-, iso- or sec-butyl, pentyl, Hexyl, heptyl or octyl.
• A stands out for difluoromethyl, trifluoromethyl, fluorodichloromethyl, chlorodifluoromethyl, trichloromethyl, 1,1,2,2-tetrafluoroethyl or pentafluoroethyl, in particular for trifluoromethyl.
• Q preferably represents oxygen
• Q also preferably represents sulfur.
• R 1 preferably represents hydrogen, in each case optionally substituted by hydroxy, cyano, halogen, -CC alkoxy or CrC 4 -haloalkoxy-Ci-Cio-alkyl or (C r C ⁇ o-alkyl) carbonyl, each optionally by cyano or halogen-substituted C 2 -C 0 -alkenyl or (C 2 -C ⁇ o-alkenyl) carbonyl, for each optionally substituted by cyano, halogen, -C - alkyl or C 1 -C 4 -haloalkyl-substituted C3-C 6 -cycloalkyl or (C 3 -C 6 cycloalkyl) carbonyl, for each optionally substituted by nitro, cyano, halogen, CC-alkyl, CC -halogen al yl, -C-C 4 alkoxy or CC 4 -haloalkoxy substituted C 6
• R 1 particularly preferably represents hydrogen, in each case methyl, ethyl, n- substituted by cyano, fluorine, chlorine, bromine, methoxy, ethoxy, n- or iso-propoxy, n-, iso-, sec- or tert-butoxy or iso-propyl, n-, iso-, sec- or tert-butyl, n-, iso-, sec-, tert- or neo-pentyl, acetyl, propionyl, n- or iso-butyroyl, each optionally by cyano , Fluorine, chlorine or bromine-substituted propenyl, butenyl, pentenyl, propenylcarbonyl, butenylcarbonyl or pentenylcarbonyl, for in each case optionally substituted by cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or isopropyl substitute
• R 1 very particularly preferably represents hydrogen, in each case methyl, ethyl, n- or isopropyl, n-, iso- or sec-butyl which is optionally substituted by cyano, fluorine, chlorine, methoxy, ethoxy, n- or iso-propoxy , Acetyl, propionyl, n- or iso-butyroyl, for propenyl, butenyl, propenylcarbonyl or butenylcarbonyl, each optionally substituted by fluorine or chlorine, for each optionally substituted by fluorine, chlorine or methyl
• R 1 particularly preferably represents hydrogen.
• R 2 preferably represents hydrogen, represents optionally cyano-, halogen- or C 4 - alkoxy-substituted CC 10 alkyl, (C ⁇ -C ⁇ 0 -alkyl) carbonyl or (C C ⁇ o alkoxy) carbonyl, or represents optionally cyano-, halogen- or C 4- alkyl substituted C 3 -C 6 cycloalkyl, for each optionally substituted by nitro, cyano, halogen, CC-alkyl, C r C -haloalkyl, -C-C alkoxy or CC 4 -haloalkoxy substituted C 6 -C ⁇ 0 -aryl or C 6 -aryl -C ⁇ 0-C ⁇ -C 4 - alkyl, or optionally nitro, cyano, halogen, -C alkyl, CC 4 haloalkyl, CC CC 4 -alkoxy or haloalkoxy substituted heterocyclyl having
• R 2 particularly preferably represents hydrogen, in each case optionally by cyano, fluorine, chlorine, bromine, methoxy, ethoxy, n- or iso-propoxy, n-, iso-, sec- or tert-butoxy substituted methyl, ethyl, n- or iso-propyl, n-, iso-, sec- or tert-butyl, acetyl, propionyl, n- or iso-butyroyl, methoxycarbonyl, ethoxycarbonyl, n- or iso-propoxycarbonyl, for each cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl optionally substituted by cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or iso-propyl, for each optionally by nitro, cyano, fluorine, chlorine, bromine, iodine, methyl,
• R 2 very particularly preferably represents hydrogen, in each case methyl, ethyl, n- or isopropyl, acetyl, propionyl, methoxycarbonyl or ethoxycarbonyl optionally substituted by cyano, fluorine, chlorine, methoxy, ethoxy, n- or iso-propoxy in each case optionally substituted by fluorine, chlorine or methyl, cyclopropyl, cyclopentyl or cyclohexyl, for in each case optionally by nitro, cyano, fluorine, chlorine, bromine, iodine, methyl, ethyl, n- or iso-propyl, n-, iso-, sec- or tert-butyl, fluoromethyl, chlor
• R 2 particularly preferably represents hydrogen or methyl.
• R 3 preferably represents optionally substituted by 'cyano, halogen or C r C -alkoxy-C ⁇ C_O-alkyl, represents optionally cyano-, halogen or C 4 -alkyl-substituted C 3 -
• C 6 cycloalkyl for each optionally by nitro, cyano, halogen, CC alkyl, -C 4 - Haloalkyl, CC 4 -alkoxy or CC -haloalkoxy substituted C 6 -C ⁇ o-A_yl or C 6 - C ⁇ o-aryl-C ⁇ -C 4 -alkyl, or for optionally nitro, cyano, halogen, CC -alkyl, CC 4 - haloalkyl, CC 4 -alkoxy or C ⁇ -C 4 haloalkoxy substituted heterocyclyl having up to 6 carbon atoms and at least one heteroatom from the series N, O, S.
• R 3 particularly preferably represents in each case optionally substituted by cyano, fluorine, chlorine, bromine, methoxy, Ethoxy, n- or iso-propoxy, n-, iso-, sec- or tert-butoxy substituted methyl, ethyl, n- or iso-propyl, n-, iso-, sec- or tert-butyl, for each optionally by Cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or iso-propyl-substituted cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl, each optionally with nitro, cyano, fluorine, chlorine, bromine, iodine, methyl, ethyl, n- or isopropyl, n-, iso-, sec- or tert-butyl,
• R 3 very particularly preferably represents in each case optionally by cyano, fluorine, chlorine,
• R 3 particularly preferably represents methyl, ethyl, isopropyl, isobutyl, tert-butyl, trifluoromethyl, 1,1,2,2-tetrafluoroethyl, pentafluoroethyl, 1-chloro-cyclopropyl, phenyl, bromophenyl, nitrophenyl, Methoxyphenyl, methylphenyl, naphthyl, 2-furyl, 3-furyl, 2-thienyl or 3-thienyl.
• R 3 stands for methyl, ethyl, isopropyl.
• R 2 and R 3 also together preferably represent C 3 -C 5 alkanediyl (alkylene).
• R 2 and R 3 together also particularly preferably represent propane-1,3-diyl (trimethylene), butane-1,4-diyl (tetramethylene) or pentane-1,5-diyl (pentamethylene).
• R 2 and R 3 together also very particularly preferably represent propane-1,3-diyl (trimethylene) or butane-1,4-diyl (tetramethylene).
• R 4 preferably represents hydrogen, amino, each optionally substituted by hydroxy, cyano, halogen or -CC 4 -alkoxy -CC-alkyl, (-CIO-alkyl) carbonyl, C
• Alkenyl, (C 2 -C ⁇ o-alkenyl) carbonyl or Qr o-alkynyl Alkenyl, (C 2 -C ⁇ o-alkenyl) carbonyl or Qr o-alkynyl.
• R 4 particularly preferably stands for hydrogen, for amino, for each methyl optionally substituted by hydroxyl, cyano, fluorine, chlorine, bromine, methoxy, ethoxy, n- or iso-propoxy, n-, iso-, sec- or tert-butoxy , Ethyl, n- or iso-propyl, n-, iso-, sec- or tert-butyl, acetyl, propionyl, n- or iso-butyroyl, methylsulfonyl, ethylsulfonyl, n- or iso-propylsulfonyl, n-, iso-, sec- or tert-butylsulfonyl, methylamino, ethylamino, n- or iso-propylamino, n-, iso-, sec- or tert-butyl_unino, acetylamino
• Pentenylcarbonyl propynyl, butynyl or pentynyl.
• R 4 very particularly preferably represents hydrogen, amino, methyl which is optionally substituted by cyano, fluorine, chlorine, bromine, methoxy, ethoxy, n- or isopropoxy,
• R 4 particularly preferably represents hydrogen or methyl.
• R 5 preferably represents hydrogen, optionally hydroxyl-, cyano-, halogen or - C 4 alkoxy-substituted C C ⁇ 0 alkyl, optionally substituted by cyano or halogen-substituted C 2 -C ⁇ o alkenyl or C 2 -C 10 alkynyl , represents optionally cyano-, halogen or C.
• R 5 particularly preferably represents hydrogen, in each case methyl, ethyl, n- or isopropyl, n-, iso- or sec- optionally substituted by hydroxyl, cyano, fluorine, chlorine, methoxy, ethoxy, n- or iso-propoxy.
• Propoxy, n-, iso-, sec- or tert-butoxy substituted phenyl is substituted) substituted phenyl, naphthyl, benzyl, phenylethyl or naphthylmethyl, or for each optionally by nitro, cyano, fluorine, chlorine, bromine, iodine, methyl, ethyl , n- or iso-propyl, n-, iso-, sec- or tert-butyl, fluoromethyl, chloromethyl, difluoromethyl, dichloromethyl, trifluoromethyl, trichloromethyl, methoxy, ethoxy, n- or iso-propoxy, n-, iso-, sec- or tert-butoxy, fluoromethoxy, difluoromethoxy, trifluoromethoxy, chlorodifluoromethoxy, fluoroethoxy, chlorine ethoxy, difluoroethoxy, dichlor
• R 5 very particularly preferably represents hydrogen, in each case methyl, ethyl, n- or isopropyl, n-, iso- or sec-butyl which is optionally substituted by cyano, fluorine, chlorine, methoxy, ethoxy, n- or iso-propoxy , for propenyl, butenyl, propynyl or butynyl optionally substituted by fluorine, chlorine or bromine, for each optionally substituted by fluorine,
• Saturated or unsaturated hydrocarbon radicals such as alkyl or alkenyl
• Optionally substituted radicals can be mono- or polysubstituted, and in the case of multiple substitutions the substituents can be the same or different.
• Residues substituted by halogen such as haloalkyl, are halogenated once or more than once. In the case of multiple halogenation, the halogen atoms can be the same or different.
• Halogen stands for fluorine, chlorine, bromine and iodine, in particular for fluorine, chlorine and bromine.
• radical definitions listed above apply both to the compounds of the formula (I) and correspondingly to the starting ec or intermediate products required in each case for the preparation. These radical definitions can be combined with one another, that is to say also between the specified preferred ranges.
• a A stands for haloalkyl
• Q A stands for oxygen or sulfur
• R 1A represents hydrogen or represents optionally substituted alkyl, alkylcarbonyl, cycloalkyl, cycloalkylcarbonyl, aryl, arylcarbonyl, arylalkyl or arylalkylcarbonyl
• R 2A represents hydrogen or represents optionally substituted alkyl, alkylcarbonyl, alkoxycarbonyl, cycloalkyl, aryl, arylalkyl or heterocyclyl stands
• R 3A for optionally substituted alkyl, cycloalkyl, aryl, arylalkyl or heterocyclyl
• R 2A and R 3A also together represent alkanediyl (alkylene),
• R 4A stands for hydrogen, for amino, or for optionally optionally substituted alkyl, alkylcarbonyl, alkylsulfonyl, alkylamino, alkylcarbonylamino, alkylsulfonylamino, alkenyl, alkenylcarbonyl or alkynyl, and
• R 5A stands for optionally substituted alkyl (with at least 2 carbon atoms), alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, aryl, arylalkyl, heterocyclyl or heterocyclylalkyl.
• a A preferably represents -C 8 haloalkyl.
• a ⁇ particularly preferably represents C r C 5 -alkyl substituted by fluorine and / or chlorine.
• Ethyl, n-propyl or iso-propyl (such as trifluoromethyl, difluoromethyl, pentafluoroethyl,
• a A particularly preferably represents trifluoromethyl.
• Q A preferably represents oxygen
• Q A also preferably represents sulfur.
• R preferably represents hydrogen, in each case optionally by cyano, halogen or C.
• Cycloalkyl) carbonyl represents in each case optionally substituted by nitro, cyano, halo, C ⁇ -C 4 -alkyl, C haloalkyl, C ⁇ -C4 alkoxy or haloalkoxy CC substituted C 6 -C ⁇ 0 -aryl or (C 6 - C 10 aryl) carbonyl, or represents in each case optionally substituted by nitro, cyano, halo, C ⁇ -C 4 - yl Al, C ⁇ -C 4 haloalkyl, C_-C 4 alkoxy or C ⁇ -C -haloalkoxy substituted (C 6 - C ⁇ 0 - aryl) -C ⁇ -C 4 alkyl or (C 6 -C ⁇ 0 aryl-C C 4 alkyl) carbonyl.
• R 1A particularly preferably represents hydrogen, in each case methyl, ethyl, n- substituted by cyano, fluorine, chlorine, bromine, methoxy, ethoxy, n- or iso-propoxy, n-, iso-, sec- or tert-butoxy or iso-propyl, n-, iso-, sec- or tert-butyl, n-, iso-, sec-, tert- or neo-pentyl, acetyl, propionyl, n- or iso-butyroyl, each optionally by cyano , Fluorine, chlorine or bromine substituted propenyl, butenyl, pentenyl, propenylcarbonyl,
• Butenylcarbonyl or pentenylcarbonyl each optionally by cyano, fluorine, Chlorine, bromine, methyl, ethyl, n- or iso-propyl substituted cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylcarbonyl, cyclobutylcarbonyl, cyclopentylcarbonyl or cyclohexylcarbonyl, each optionally with nitro, cyano, fluorine, chlorine, bromine, iodine, methyl, ethyl , n- or iso-propyl, n-, iso-, sec- or tert-butyl, fluoromethyl, chloromethyl, difluoromethyl, dichloromethyl, trifluoromethyl, trichloromethyl, methoxy,
• R 1A very particularly preferably represents hydrogen.
• R 2A is preferably hydrogen, represents optionally cyano-, halogen or C ⁇ -C 4 - (. C ⁇ -C -alkyl) alkoxy -Cio-alkyl, carbonyl, or (CC 10 alkoxy) carbonyl, optionally substituted by cyano, Halogen or -CC alkyl substituted C 3 -C 6 cycloalkyl, for each optionally by nitro, cyano, halogen, C] -C 4 alkyl, C_-C haloalkyl, -C-C 4 alkoxy or CC 4 - haloalkoxy substituted C 6 -aryl -C ⁇ 0 or C ⁇ -Cio-aryl-Ci-Gr alkyl, or optionally nitro, cyano, halo, C ⁇ -C 4 -alkyl, C 4 haloalkyl, CC alkoxy or C ⁇ - C 4 -haloalkoxy substituted heterocyclyl with up to
• R 2A particularly preferably represents hydrogen, in each case optionally substituted by cyano, fluorine, chlorine, bromine, methoxy, ethoxy, n- or iso-propoxy, n-, iso-, sec- or tert-butoxy, methyl, ethyl, n- or iso-propyl, n-, iso-, sec- or tert-butyl, acetyl, propionyl, n- or iso-butyroyl, methoxycarbonyl, ethoxycarbonyl, n- or iso-propoxycarbonyl, for each optionally by cyano, fluorine, chlorine, Bromine, methyl, ethyl, n- or iso-propyl-substituted cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl, each optionally with nitro, cyano, fluorine, chlorine, bromine, iodine
• R 2A very particularly preferably represents hydrogen, in each case methyl, ethyl, n- or iso- which is optionally substituted by cyano, fluorine, chlorine, methoxy, ethoxy, n- or iso-propoxy.
• R 3A preferably represents alkyl with 1 to 10 carbon atoms optionally substituted by cyano, halogen or CC alkoxy, for cycloalkyl optionally substituted by cyano, halogen or C 1 -C 4 alkyl with 3 to 6 carbon atoms, each optionally substituted by nitro, cyano , Halogen, -CC alkyl, -C -haloalkyl, CC alkoxy or -C - haloalkoxy substituted aryl or arylalkyl each having 6 or 10 carbon atoms in the aryl group and optionally 1 to 4 carbon atoms in the alkyl part, or for optionally nitro, Cyano, halogen, -CC 4 -alkyl, Q- -haloalkyl, - -alkoxy or CC 4 -haloalkoxy-substituted heterocyclyl with up to 6 carbon atoms and at least one heteroatom from the series N, O,
• R 3A is particularly preferred for each methyl optionally substituted by cyano, fluorine, chlorine, bromine, methoxy, ethoxy, n- or iso-propoxy, n-, iso-, sec- or tert-butoxy, Ethyl, n- or iso-propyl, n-, iso-, sec- or tert-butyl, for each cyclopropyl, cyclobutyl, cyclopentyl substituted by cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or iso-propyl or cyclohexyl, each optionally with nitro, cyano, fluorine, chlorine, bromine, iodine, methyl, ethyl, n- or isopropyl, n-, iso-, sec- or tert-butyl, fluoromethyl, chloromethyl, difluoromethyl, dichloromethyl , Trifluor
• R 3A very particularly preferably represents methyl, ethyl, n- or isopropyl, isobutyl or tert-butyl, each optionally substituted by fluorine, chlorine, methoxy, ethoxy, n- or iso-propoxy, each in each case optionally by fluorine, Chloro or methyl substituted cyclopropyl, cyclopentyl or cyclohexyl, each optionally with nitro, cyano, fluorine,
• R 3A particularly preferably represents methyl, ethyl, isopropyl, isobutyl, tert-butyl,
• R 2A and R 3A also together preferably represent C 3 -C 5 alkanediyl (alkylene).
• R 2A and R 3A together also particularly preferably represent propane-1,3-diyl (trimethylene), butane-1,4-diyl (tetramethylene) or pentane-1,5-diyl (pentamethylene).
• R 2 ⁇ and R 3A also together very particularly preferably represent propane-1,3-diyl (trimethylene) or butane-1,4-diyl (tetramethylene).
• R A preferably represents hydrogen, represents amino, in each case optionally substituted by cyano, halogen or CC-alkoxy-C 1 -C 10 -alkyl, (C 1 -C 8 -alkyl) carbonyl, C 1 -C 10 -alkylsulfonyl, C C ⁇ o-All_y__u ⁇ _no , (-Cio-Alkytycarbonyl ⁇ miino or Ci-Cio-Alkylsulfonylamino, or for each optionally substituted by halogen substituted C 2 -C 10 alkenyl, (C 2 -C ⁇ 0 alkenyl) carbonyl or C 2 -C ⁇ 0 alkynyl.
• R 4A particularly preferably represents hydrogen, amino, in each case optionally by cyano, fluorine, chlorine, bromine, methoxy, ethoxy, n- or iso-propoxy, n-, iso-, sec- or tert-
• Pentenylcarbonyl propynyl, butynyl or pentynyl.
• R 4A very particularly preferably represents hydrogen, amino, methyl which is optionally substituted by cyano, fluorine, chlorine, bromine, methoxy, ethoxy, n- or isopropoxy,
• R 4A particularly preferably represents hydrogen or methyl.
• R 5A preferably represents optionally cyano-, halogen or C r C -alkoxy-substituted C 2 -C ⁇ o-Al_cyl, in each case optionally halogen-substituted C 2 -alkenyl or -C ⁇ 0
• C 2 -C 8 -alkynyl for C 3 - which is optionally substituted by cyano, halogen or C 1 -C 4 -alkyl C ö cycloalkyl or C 3 -C 6 cycloalkyl -CC 4 -alkyl, for each optionally by nitro, cyano, halogen, CC 4 -alkyl, C r C 4 -haloalkyl, CC 4 -alkoxy, CC 4 - Haloalkoxy, CC alkylthio, C 1 -C 4 haloalkylthio, phenyl, phenoxy or piperazinyl (which is optionally substituted by C 1 -C 4 alkyl or by phenyl which is optionally substituted by halogen, C 1 -C 4 alkyl or CC alkoxy) substituted C) 6 -C ⁇ 0 aryl or C 6 -C ⁇ 0 -
• R 5A particularly preferably represents ethyl, n- or iso-propyl, n-, iso- or sec-butyl, optionally substituted by hydroxy, cyano, fluorine, chlorine, methoxy, ethoxy, n- or iso-propoxy, in each case if appropriate propenyl, butenyl, pentenyl, propynyl, butynyl or pentynyl substituted by cyano, fluorine, chlorine or bromine, for cyclopropyl, cyclobutyl optionally substituted by cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or isopropyl, Cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl or cyclohexylmethyl, for each optionally by nitro, cyano, fluorine, chlorine, bromine, iod
• Propoxy, n-, iso-, sec- or tert-butoxy substituted phenyl is substituted) substituted phenyl, naphthyl, benzyl, phenylethyl or naphthylmethyl, or for each optionally by nitro, cyano, fluorine, chlorine, bromine, iodine, methyl, ethyl , n- or iso-propyl, n-, iso-, sec- or tert-butyl, fluoromethyl, chloromethyl, difluoromethyl, dichloromethyl, trifluoromethyl, trichloromethyl, methoxy, ethoxy, n- or iso-propoxy, n-, iso-, sec- or tert-butoxy, fluoromethoxy, difluoromethoxy, trifluoromethoxy, chlorodifluoromethoxy, fluoroethoxy, chloroethoxy, difluoroethoxy, dichlor
• R 5A very particularly preferably represents ethyl, n- or iso-propyl, n-, iso- or sec-butyl, optionally substituted by cyano, fluorine, chlorine, methoxy, ethoxy, n- or iso-propoxy, each in each case by Fluorine, chlorine or bromine-substituted propenyl,
• Propyl, methoxy, ethoxy, n- or iso-propoxy substituted phenyl is substituted) substituted phenyl, benzyl or phenylethyl, or for each optionally by nitro, cyano, fluorine, chlorine, bromine, iodine, methyl, ethyl, n- or iso- Propyl, n-, iso-, sec- or tert-butyl, fluoromethyl, chloromethyl, difluoromethyl, dichloromethyl, trifluoromethyl, trichloromethyl, methoxy, ethoxy, n- or iso-propoxy, n-, iso-, sec- or tert-butoxy , Fluoromethoxy, difluoromethoxy, trifluoromethoxy, chlorodifluoromethoxy, fluoroethoxy, chloroethoxy, difluoroethoxy, dichloroethoxy, fluorochloroe
• a A represents C 1 -C 8 -alkyl substituted by fluorine and / or chlorine
• Q A represents oxygen or sulfur
• R 3A for methyl, ethyl, iso-propyl, iso-butyl, tert-butyl, 1-chloro-cyclopropyl, phenyl, 2-furyl, 3-
• R 5A each represents ethyl, n- or iso-propyl, n-, iso-, optionally substituted by hydroxy, cyano, fluorine, chlorine, methoxy, ethoxy, n- or iso-propoxy or sec-butyl, for propenyl, butenyl, pentenyl optionally substituted by cyano, fluorine, chlorine or bromine,
• Q A represents oxygen or sulfur
• R 3A for methyl, ethyl, iso-propyl, iso-butyl, tert-butyl, 1-chloro-cyclopropyl, phenyl, 2-furyl, 3-
• R 5A is cyclohexyl, each optionally by nitro, cyano, fluorine, chlorine, bromine, iodine, methyl, ethyl, n- or iso-propyl, n-, iso-, sec - or tert-butyl, fluoromethyl, chloromethyl, difluoromethyl, dichloromethyl, trifluoromethyl, trichloromethyl, methoxy, ethoxy, n- or iso-propoxy, fluoromethoxy, difluoromethoxy, trifluoromethoxy, chlorodifluoromethoxy, fluoroethoxy, chloroethoxy, difluoroethoxy, dichloroethoxy, Fluorchlorethoxy or trifluoroethoxy, methylthio , Ethylthio, n- or iso-propylthio, difluoromethylthio, triflu
• Methoxy, ethoxy, n- or iso-propoxy substituted phenyl is substituted) substituted phenyl, benzyl, phenylethyl or pyridinyl.
• Saturated or unsaturated hydrocarbon residues such as alkyl or alkenyl can also be used in connection with heteroatoms, e.g. in alkoxy, where possible, be straight-chain or branched.
• Optionally substituted radicals can be mono- or polysubstituted, and in the case of multiple substitutions the substituents can be the same or different.
• Halogen substituted residues such as e.g. Haloalkyl, are halogenated once or several times. , In the case of multiple halogenation, the halogen atoms can be the same or different.
• Halogen stands for fluorine, chlorine, bromine and iodine, in particular for fluorine, chlorine and bromine.
• the new trifluoromethylpyrazolinols and their derivatives of the formula (LA) - and analogously also the partially known pyrazolinols and their derivatives of the formula (I) - are obtained by (a) 1,3-dicarbonyl compounds of the general formula (H) in which R 2A and R 3A have the meaning given above, with (thio) semicarbazides of the general formula (HI)
• R 2A and R 3A have the meaning given above and R represents alkyl
• X represents halogen, or with iso (thio) cyanates of the general formula (VH)
• R 5A with the exception of H (hydrogen) has the meaning given above, optionally in the presence of one or more diluents and, if appropriate, in
• the compounds of the formula (IA) in which R 1A is H (hydrogen) can be converted by conventional methods into corresponding compounds of the formula (LA) in which R 1A has the other meanings given above, generally by reaction with compounds of the formula X'-R ⁇ (VLLl), in which R 1A, with the exception of hydrogen, has the meaning given above and X 1 is halogen, preferably in the presence of reaction auxiliaries, such as, for example, triethylamine or ethyldiisopropylamine , and optionally in the presence of diluents, such as, for example, tetrahydrofuran, 1,4-dioxane, methyl isobutyl ketone, N, N-dimethylformamide or N, N-dimethyl-acetamide, at temperatures between 0 ° C. and 200 ° C. Diazomethane or trimethyloxonium tetrafluoroborate can also be used for the methylation.
• Formula (H) provides a general definition of the 1,3-dicarbonyl compounds to be used as starting materials in process (a) according to the invention for the preparation of the compounds of the general formula (LA).
• R 2A and R 3A have preferred, particularly preferably, very particularly preferably, etc. those meanings which are preferred as particularly preferred above in connection with the description of the compounds of the general formula (LA) according to the invention , very particularly preferred, etc. for these residues.
• the starting materials of the general formula (S) are known and / or can be prepared by processes known per se [cf. J. Fluorine Chem. 118: 135-148 (2002); J. Med. Chem. 40 (1997), 1347-1365; Synthesis 11: 1321-1324 (1997); Tetrahedron Lett. 43 (2002), 8701-8705].
• Formula (TV) provides a general definition of the alkoxyalkenyl ketones to be used as starting materials in process (b) according to the invention for the preparation of the compounds of the general formula (IA).
• R 2A and R 3A preferably, particularly preferably, very particularly preferably etc. have all those meanings which have already been mentioned above as preferred, particularly preferred in connection with the description of the compounds of the general formula (IA) according to the invention particularly preferred, etc. for these residues.
• the starting materials of the general formula (IV) are known and / or can be prepared by processes known per se [cf. Chem. Ber. 115: 2766 (1982); ibid. 1984, 117: 3270; Chem. Lett. 1976, 499-502; J. Fluorine Chem. 99: 177-182 (1999); Synthesis 1986, 1013-1014; ibid. 1991, 483; Preparation Examples].
• Formula (DL) provides a general definition of the (thio) semicarbazides to be used further as starting materials in processes (a) and (b) for the preparation of the compounds of the general formula (IA).
• Q A R 4A and R 5A have preferred, particularly preferably, very particularly preferably etc. those meanings which have been particularly preferred above in connection with the description of the compounds of the general formula (LA) according to the invention , very particularly preferred, etc. for these residues.
• the starting materials of the general formula (HL) are known and / or can be prepared by processes known per se [cf. Arch. Pharm. 335 (2002), 129-134; Bioorg. Med. Chem. Lett. 11: 1149-1152 (2001); Egypt. J. Chem. 41: 257-266 (1998); Org. Synth. Collect. Vol. 5 (1973), 168-170; Pharmazie 55 (2000), 500-502; ibid. 56: 121-124 (2001); Preparation Examples].
• Formula (V) provides a general definition of the pyrazolinols to be used as starting materials in process (c) according to the invention for the preparation of the compounds of the general formula (LA).
• R 2A and R 3A have preferred, particularly preferably, very particularly preferably etc. those meanings which have been preferred as particularly preferred above in connection with the description of the compounds of the general formula (LA) according to the invention , very particularly preferred, etc. for these residues.
• the starting materials of the general formula (V) are known and / or can be prepared by processes known per se [cf. Chem. Het. Comp. 38: 668-676 (2002); J. Fluorine Chem. 94: 199-203 (1999); Soot. Chem. Bull. 51 (2002), 1280-1291; Preparation Examples].
• Formula (VL) provides a general definition of the aminocarbonyl compounds to be used as starting materials in process (c) according to the invention for the preparation of the compounds of the general formula (LA).
• Q A , R A and R 5A have preferred, particularly preferably, very particularly preferably etc. those meanings which are particularly preferred above in connection with the description of the compounds of the general formula (IA) according to the invention preferred, very particularly preferred, etc. for these radicals have been specified.
• X preferably represents chlorine.
• Arninocarbonyl compounds of formula (VI) are known organic synthetic chemicals.
• Formula (VH) provides a general definition of the iso (thio) cyanates to be used alternatively as starting materials in process (c) according to the invention for the preparation of the compounds of the general formula (IA).
• Q A and R 5A have preferred, particularly preferably, very particularly preferably etc. those meanings which have already been preferred as particularly preferred above in connection with the description of the compounds of the general formula (LA) according to the invention , very particularly preferred, etc. for these residues.
• Iso (thio) cyanates of the formula (VH) are known organic synthetic chemicals.
• the processes (a), (b) and (c) according to the invention for the preparation of the compounds of the general formula (LA) are preferably carried out using one or more diluents.
• Inert organic solvents are particularly suitable as diluents for carrying out processes (a), (b) and (c) according to the invention.
• aliphatic, alicyclic or aromatic optionally halogenated hydrocarbons, such as, for example, gasoline, benzene, toluene, xylene, chlorobenzene, dichlorobenzene, petroleum ether, hexane, cyclohexane, dichloromethane, chloroform, carbon tetrachloride; Ethers such as diethyl ether, diisopropyl ether, dioxane, tetrahydrofuran or ethylene glycol dimethyl or diethyl ether; Ketones such as acetone, butanone or methyl isobutyl ketone; Nitriles, such as acetonitrile, propionitrile or butyrometrile; Amides such as N, N-dimethylformamide, N, N-dimethylacetamide, N-methylformanilide, N-methylpyrrolidone or hexamethylphosphoric triamide; Esters such as N, N-d
• reaction auxiliaries for the preparation of the compounds of the general formula (J) are optionally carried out using one or more reaction auxiliaries.
• the usual inorganic or organic bases or acid acceptors are generally suitable as reaction aids for the processes according to the invention. These preferably include alkali metal or alkaline earth metal acetate, amides, carbonates, bicarbonates, hydrides, hydroxides or alkanolates, such as sodium, potassium or calcium acetate.
• reaction temperatures can be varied within a substantial range when carrying out processes (a), (b) and (c). In general, temperatures between 0 ° C and 150 ° C, preferably between 10 ° C and 120 ° C.
• the processes (a), (b) and (c) according to the invention are generally carried out under normal pressure. However, it is also possible to carry out the processes according to the invention under elevated or reduced pressure - generally between 0.1 bar and 10 bar.
• the starting materials are generally used in approximately equimolar amounts. However, it is also possible to use one of the components in a larger excess.
• the reaction is generally carried out in a suitable diluent in the presence of a reaction auxiliary and the reaction mixture is generally stirred at the required temperature for several hours. Working up is carried out according to customary methods (cf. the production examples).
• the active ingredients are suitable for protecting plants and plant organs, for increasing crop yields, improving the quality of the crop and for combating animal pests, in particular insects, arachnids and nematodes, which are used in agriculture , in forests, in gardens and leisure facilities, in the protection of stored goods and materials as well as in the hygiene sector. They can preferably be used as pesticides. They are effective against normally sensitive and resistant species as well as against all or individual stages of development.
• the pests mentioned above include: From the order of the Isopoda, for example Oniscus asellus, Armadillidium vulgare, Porcellio scaber. From the order of the Diplopoda, for example, Blaniulus guttulatus. From the order of the Chilopoda, for example, Geophilus carpophagus and Scutigera spp.
• 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, Thrips palmi,
• Nephotettix cincticeps Lecanium corni, Saissetia oleae, Laodelphax striatellus, Nilaparvata lugens,
• Ephestia kuehniella Galleria mellonella, Tineola bisselliella, Tinea pellionella, Hofmannophila pseudospretella, Cacoecia podana, Capua reticulana, Choristoneura fumiferana, Clysia ambiguella, Homona magnanima, Tortrix viridana, Cnapehalocerus s.
• Oryzaephüus surinamensis Anthonomus spp., Sitophilus spp., Otiorrhynchus sulcatus, Cosmopolites sordidus, Ceuthorrhynchus assimilis, Hypera postica, Dermestes spp., Trogoderma spp., Anthrenus spp., Attagenusespp., Melctinespp.
• Niptus hololeucus gibbium psylloides, Tribolium spp., Tenebrio molitor, Agriotes spp., Conoderus spp., Melolontha melolontha, Amphimallon solstitialis, Costelytra zealandica, Lissorhoptrus oryzophilus.
• Hymenoptera e.g. Diprion spp., Hoplocampa spp., Lasius spp., Monomorium pharaonis, Vespa spp. From the order of the Diptera e.g.
• Chorioptes spp. Chorioptes spp., Sarcoptes spp., Tarsonemus spp., Bryobia praetiosa, Panonychus spp., Tetranychus spp., Hemitarsonemus spp., Brevipalpus spp.
• Plant-parasitic nematodes include e.g. Pratylenchus spp., Radopholus similis, Ditylenchus dipsaci, Tylenchulus semipenetrans, Heterodera spp., Globodera spp., Meloidogyne spp., Aphelenchoides spp., Longidorus spp., Xiphinema spp., Trichodorus spp., Bursaph.
• the compounds of the formula (L) according to the invention are particularly notable for strong action against aphids (for example Myzus persicae), beetles and the corresponding larvae (for example Phaedon cochleariae), caterpillars (for example Spodoptera frugiperda), spider mites (for example Tetranychus urticae), fleas (for example Ctenocephalides felis) ,. Flies and the corresponding larvae (e.g. Lucilia cuprina) and nematodes (e.g. Meloidogyne incognita).
• aphids for example Myzus persicae
• beetles and the corresponding larvae for example Phaedon cochleariae
• caterpillars for example Spodoptera frugiperda
• spider mites for example Tetranychus urticae
• fleas for example Ctenocephalides felis
• Flies and the corresponding larvae e.g.
• the compounds according to the invention can also be used in certain concentrations or application rates as herbicides or as safeners for herbicides, or as microbicides, for example as fungicides, antifungal agents 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 undesired wild plants or crop plants (including naturally occurring crop plants).
• Cultivated 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 by Plant variety rights of protectable or non-protectable plant varieties.
• Plant parts are to be understood to mean all above-ground and underground parts and organs of the plants, such as shoots, leaves, flowers and roots, examples being leaves, needles, stems, stems, flowers, fruiting bodies, fruits and seeds as well as roots, tubers and rhizomes.
• the plant parts also include crops and vegetative and generative propagation material, for example cuttings, tubers, rhizomes, offshoots and seeds.
• 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 using the customary treatment methods, e.g. by dipping, spraying, vaporizing, atomizing, scattering, spreading, injecting and, in the case of propagation material, in particular in the case of seeds, furthermore by single- or multi-layer coating.
• the active compounds can be converted into the customary formulations, such as solutions, emulsions, wettable powders, suspensions, powders, dusts, pastes, soluble powders, granules, suspension emulsion concentrates, active substance-impregnated natural and synthetic substances and very fine encapsulations in polymeric substances.
• formulations are 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.
• organic solvents can also be used as auxiliary solvents.
• auxiliary solvents e.g. organic solvents
• aromatics such as xylene, toluene, or alkylnaphthalenes
• chlorinated aromatics and chlorinated aliphatic hydrocarbons such as chlorobenzenes, chlorethylenes or methylene chloride
• aliphatic hydrocarbons such as cyclohexane or paraffins, e.g.
• Petroleum fractions mineral and vegetable oils, alcohols such as butanol or glycol and their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as dimethylformamide and dimethyl sulfoxide, and water.
• 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.
• Solid carriers are possible: e.g. Ammonium salts and natural rock flour, 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, as solid
• Carriers for granules are possible: eg 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 stalks;
• Possible emulsifiers and / or foam-generating agents are: for example nonionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates and protein hydrolyzates;
• the following may be used as dispersants: for example lignin sulfite waste liquor and methyl cellulose.
• Adhesives such as carboxymethyl cellulose, natural and synthetic see powdery, granular or latex-shaped polymers, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, and natural phospholipids, such as cephalins and lecithins and synthetic phospholipids, can be used in the formulations.
• Other additives can be mineral and vegetable oils.
• Dyes such as inorganic pigments, e.g. Iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo and metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc can be used.
• the formulations generally contain between 0.1 and 95% by weight of active compound, preferably between 0.5 and 90%.
• the active substance according to the invention can be present in its commercially available formulations and in the use forms prepared from these formulations in a mixture with other active substances, such as insecticides, attractants, sterilants, bactericides, acaricides, nematicides, fungicides, growth-regulating substances or herbicides.
• Insecticides include, for example, phosphoric acid esters, carbamates, carboxylic acid esters, chlorinated hydrocarbons, phenylureas, substances produced by microorganisms, etc.
• fungicides 2-phenylphenol; 8-hydroxyquinoline sulfates; Acibenzolar-S-methyl; aldimorph; amidoflumet; Ampropylfos; Ampropylfos-potassium; andoprim; anilazine; azaconazole; azoxystrobin; benalaxyl; Benodanil; benomyl; Benthiavalicarb-isopropyl; Benzamacril; Benzamacril-isobutyl; bilanafos; binapacryl; biphenyl; bitertanol; Blasticidin-S; bromuconazole; Bupirimate; Buthiobate; butylamine; Calcium polysulfide; capsimycin; captafol; captan; carbendazim; carboxin; carpropamid; carvones; Quinomethionate; Chlobenthiazone; Chlor
• Bactericides bronopol, dichlorophene, nitrapyrin, nickel-dimethyldithiocarbamate, kasugamycin, octhilinone, furan carboxylic acid, oxytetracycline, probenazole, streptomycin, tecloftalam, copper sulfate and others Copper preparations.
• Pyrethroids e.g. acrinathrin, allethrin (d-cis-trans, d-trans), beta-C! Yflu1brin, bifenthrin, bioallethrin, bioallethrin-S-cyclopentyl-isomer, bioethanomethrin, biopermethrin, bioresmethrin, chlorosaporhrin -Cypeimethrin, Cis-Resmethrin, Cis-Per nethrin, Clocythrin, ( ⁇ ycloprothrin, Cyfluthrin, Cyhalothrin, Cypemiethrin (alpha-, beta-, theta-, zeta-), (phenothrin, DDT, Deltamethrin, Empenthrin, IR-isomer Esfenvalerate, Etofenprox, Fenfluthrin, Fenpropathrin, Fenpyrithr
• oxadiazines e.g. indoxacarb
• acetylcholine receptor agonists / antagonists e.g. acetylcholine receptor agonists / antagonists
• CWoronicotinyle / neonicotinoids e.g. acetamiprid, clothianidin, dinotefuran, lmidacloprid, nitenpyram, nithiazine, thiacloprid, thiamethoxam
• Nicotine Bensultap, Cartap
• GABA-controlled chloride channel antagonists 5.1 Cyclodienes organochlorines (e.g. camphechlor, chlordane, endosulfan, gamma-HCH, HCH, heptachlor, lindane, methoxychlor
• organochlorines e.g. camphechlor, chlordane, endosulfan, gamma-HCH, HCH, heptachlor, lindane, methoxychlor
• Fiprole e.g. Acetoprole, Ethiprole, Fipronil, Vaniliprole
• Mectins e.g. abamectin, avermectin, emamectin, emamectin-benzoate, ivermectin, mitemectin, milbemycin
• diacylhydrazines e.g. chromafenozide, halofenozide, methoxyfenozide, tebufenozide
• Benzoyl ureas e.g. bistrifluron, chlofluazuron, diflubenzuron, fluazuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, penfluron, teflubenzuron, triflumuron.
• Buprofezin e.g. bistrifluron, chlofluazuron, diflubenzuron, fluazuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, penfluron, teflubenzuron, triflumuron.
• Organotins e.g. azocyclotin, cyhexatin, fenbutatin-oxide
• METI's e.g. Fenazaquin, Fenpyroximate, Pyrimidifen, Pyridaben, Tebufenpyrad, Tolfenpyrad
• 12.2 Hydramethylnone e.g. Fenazaquin, Fenpyroximate, Pyrimidifen, Pyridaben, Tebufenpyrad, Tolfenpyrad
• Page III electron transport inhibitors 14.1 acequinocyl, fluacrypyrim
• tetronic acids e.g. spirodiclofen, spiromesifen
• 16.2 tetramic acids [e.g. 3- (2,5-Dimethylphenyl) -8-methoxy-2-oxo-l-azaspiro [4.5] dec-3-en-4-yl ethyl carbonate (alias: Carbonic acid, 3- (2,5-dimethylphenyl) -8-methoxy-2-oxo-l-azaspiro [4.5] dec-3-en-4- yl ethyl ester, CAS Reg.-No .: 382608-10-8) and Carbonic acid, cis-3- ( 2,5-dimethyl ⁇ henyl) -8-methoxy-2-oxo-l-azaspiro [4.5] dec-3-en-4-yl ethyl ester (CAS Reg.-No .: 203313-25-1)]
• Carboxamides e.g. Flomcamid
• Octopaminergic agonists e.g. Amitraz
• Phthalamides e.g. ⁇ t ⁇ l-Dimeth l ⁇ - ⁇ e ⁇ lsulfony e ⁇ yS-iod-N ⁇ p-me yM-Cl ⁇ - tetiafluor-l ⁇ trifluoromethyl
• ethyl] phenyl] -l 2-benzenedicarboxamide (CAS Reg.No .: 272451-65-7)
• Biolog ⁇ ka hormones or pheromones (e.g. Azadirachtin, Bacillus spec, Beauveria spec, Codlemone, Metarrhizin spec, Paecilomyces spec, Thuringiensin, Verticillium spec.)
• hormones or pheromones e.g. Azadirachtin, Bacillus spec, Beauveria spec, Codlemone, Metarrhizin spec, Paecilomyces spec, Thuringiensin, Verticillium spec.
• fumigants e.g. aluminum phosphide, methyl bromide, sulfuryl fluoride
• Selective feeding inhibitors e.g. Cryolite, Flomcamid, Pymetrozine
• Mites growth inhibitors e.g. Clofentezine, Etoxazole, Hexythiazox
• the active compounds according to the invention can furthermore be present in their customary 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 compounds according to the invention can also be present in their customary formulations and in the use forms prepared from these formulations in mixtures with inhibitors which break down the active compound after use in the environment of the plant, on the surface of parts of plants or in plant Reduce tissues.
• 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 substance When used against hygiene pests and pests of stored products, the active substance is distinguished by an excellent residual action on wood and clay and by a good stability to alkali on limed substrates.
• all plants and their parts can be treated.
• wild plant species or plant species and their parts obtained by conventional biological breeding methods such as crossing or protoplast fusion
• transgenic plants and plant cultivars which have been obtained by genetic engineering methods if appropriate in combination with conventional methods (genetically modified organisms) and their parts are treated.
• the term "parts” or “parts of plants” or “plant parts” 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 varieties are understood to mean plants with new properties ("traits"), both by conventional breeding, by mutagenesis or have been grown by recombinant DNA techniques. These can be varieties, bio and genotypes.
• the treatment according to the invention can also cause superadditive (“synergistic") effects.
• superadditive for example, reduced expenditure and / or expansion of the W l mg spectrum and / or an increase in the action 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 drought or to water or soil salt content are 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 expected effects.
• the preferred transgenic (genetically engineered) plants or plant cultivars to be treated according to the invention include all plants which, through the genetic engineering modification, have received genetic material 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 crop yields, higher quality and / or higher nutritional value of the harvesting products , higher shelf life and / or workability of the harvest products.
• transgenic plants are the important cultivated plants, such as cereals (wheat, rice), corn, soybeans, potatoes, cotton, tobacco, rapeseed and fruit plants (with the fruits apples, pears, citrus fruits and grapes), with corn, soybeans, potatoes , Cotton, tobacco and rapeseed are highlighted.
• the traits that are particularly emphasized are the increased defense of the plants against insects, arachnids, nematodes and snails by toxins arising in the plants, in particular those which are caused by the genetic material from Bacillus thuringiensis (for example by the genes CryLA (a) , CryLA (b), CryLA (c), CryLLA, CryL lA, CryLLLB2, Cry9c Cry2Ab, Cry3Bb and CrylF and their combinations) are produced in the plants (hereinafter "Bt plants”).
• the properties (“traits”) also particularly emphasize the increased defense of plants against fungi, bacteria and viruses through systemic acquired resistance (SAR), systemin, phytoalexins, elicitors as well as resistance genes and speaking proteins and toxins.
• the properties (“traits”) which are particularly emphasized are the increased tolerance of the plants to certain herbicidal active compounds, for example imidazolinones, sulfonylureas, glyphosate or phosphinotricin (for example “PAT” gene).
• the genes which confer the desired properties (“traits”) can also occur in combinations with one another in the transgenic plants.
• Bt plants are maize varieties, cotton varieties, soy varieties and potato varieties that are marketed 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).
• YIELD GARD® e.g. corn, cotton, soy
• KnockOut® e.g. corn
• StarLink® e.g. corn
• Bollgard® Cotton
• Nucotn® cotton
• NewLeaf® potato
• herbicide-tolerant plants are corn varieties, cotton varieties and soy varieties which are marketed under the trade names Roundup Ready® (tolerance to glyphosates, for example corn, cotton, soybeans), Liberty Link® (tolerance to phosphinotricin, for example rapeseed), IMI® (Tolerance to imidazolinones) and STS® (tolerance to sulfonylureas such as corn).
• the herbicide-resistant plants (conventionally bred to herbicide tolerance) include the varieties sold under the name Clearfield® (eg maize). It goes without saying that these statements also apply to plant varieties developed in the future or coming onto the market in the future with these or future-developed genetic properties ("traits").
• 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 substances according to the invention act not only against pests of plants, hygiene and stored products, but also in the veterinary sector against animal parasites (ectoparasites) such as tick ticks, leather ticks, mite mites, running mites, flies (stinging and licking), parasitic fly larvae, lice, Hair lice, featherlings and fleas.
• animal parasites ectoparasites
• tick ticks leather ticks
• mite 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. From the order of the Mallophagida and the subordinates Amblycerina and Ischnocerina e.g.
• Trimenopon spp. Menopon spp., Trinoton spp., Bovicola spp., Wemec ella spp., Lepikentron 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., Lucilia spp., Chrysomyia spp., Wohlfahrtia spp., Sarcophaga spp., Oestrus spp., Hypoderma spp., Gasterophilus spp., Hippobosca spp.,
• Siphonaptrida e.g. Pulex spp., Ctenocephalides spp., Xenopsylla spp., Ceratophyllus spp.
• Supella spp. From the subclass of the Acari (Acarina) and the orders of the Meta and Mesostigmata e.g.
• Dermacentor spp. Haemophysalis spp., Hyalomma spp., Rhipicephalus spp., Dermanyssus spp.,
• Raillietia spp. Pneumonyssus 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., Hypodectes spp.
• Pterolichus spp. Psoroptes spp., Chorioptes spp., Otodectes spp., Sarcoptes spp., Notoedres spp.,
• the active compounds of the formula (I) according to the invention are also suitable for combating arthropods which are used in agricultural animals, such as 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 By fighting these arthropods, deaths and reduced performance (in meat, milk, wool, skins, eggs, honey, etc.) are to be reduced, so that the use of the active compounds according to the invention enables more economical and simple animal husbandry.
• the active compounds according to the invention are used in a known manner by enteral administration in the form of, for example, tablets, capsules, drinkers, drenches, granules, pastes, boluses, the feed-through method, suppositories, by parenteral administration, for example by Injections (intramuscular, subcutaneous, intravenous, intraperitoneal, etc.), implants, 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 active substance-containing shaped bodies, such as collars, ear tags, tail tags, limb tapes, 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 for example by Injections (intr
• the active compounds of the formula (L) can be used directly as formulations (for example powders, emulsions, flowable agents) which contain the active compounds in an amount of 1 to 80% by weight or after 100 to 10,000-fold dilution or use it as a chemical bath.
• insects may be mentioned by way of example and without limitation - beetles such as Hylotrupes bajulus, Chlorophorus pilosis, Anobium punctatum, Xestobium rufovillosum, Ptilinus pecticornis, Dendrobium pertinex, Emobius ollis, Priobium ca ⁇ ini, Lyctus africanus, Lyctus brunicanus, Lyctus brunicanus Lyctus linearis, Lyctus pubescens, Trogoxylon aequale, Minthes rugicollis, Xyleborus spec. Tryptodendron spec.
• non-living materials such as preferably plastics, adhesives, glues, papers and cartons, leather, wood, wood processing products and paints.
• the material to be protected from 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, 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 optionally dyes and pigments and other 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 optimum amount of use 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.
• 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-soluble, oily and oily solvents.
• Mineral oils with a boiling range of 170 to 220 ° C, white spirit with a boiling range of 170 to 220 ° C, spindle oil with a boiling range of 250 to 350 ° C, petroleum or aromatics with a boiling range of 160 to 280 ° C, Te ⁇ entinöl and Like. Used.
• liquid aliphatic hydrocarbons with a boiling range from 180 to 210 ° C. or high-boiling mixtures of aromatic and aliphatic hydrocarbons with a boiling range from 180 to 220 ° C. and / or locker oil and / or monochlomaphthalene, preferably ⁇ -monochlomaphthalene, are used.
• organic low-volatility oily or oily solvents with an evaporation number above 35 and a flash point above 30 ° C, preferably above 45 ° C can be partially replaced by slightly or medium-volatile organic chemical solvents, with the proviso that the solvent mixture also has an evaporation number 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 organic-chemical binders used are the water-thinnable synthetic resins which are known per se and / or 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 ,
• 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
• the synthetic resin used as a binder can be used in the form of an emulsion, dispersion or solution. Bitumen or bituminous substances up to 10% by weight can also be used as binders. In addition, known dyes, pigments, water-repellants, odor correctors and inhibitors or anticorrosive agents and the like can be used.
• At least one alkyd resin or modified alkyd resin and or a drying vegetable oil is preferably contained in the agent or in the concentrate as the organic chemical binder.
• Alkyd resins with an oil content of more than 45% by weight, preferably 50 to 68% by weight, are preferably used according to the invention.
• binder mentioned can be replaced by a lubricant (mixture) or a plasticizer (mixture). These additives are intended to volatilize the active ingredients and prevent 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, glycerol glycol ether or higher glycerol ether 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
• stearates such as butyl stearate or amy
• Fixatives 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, optionally 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 may optionally contain further insecticides and, if appropriate, one or more fungicides.
• insecticides and fungicides mentioned in WO 94/29268 are preferably suitable as additional admixing partners.
• the compounds mentioned in this document are an integral part of the present application.
• Insecticides such as Chlo ⁇ yriphos, Phoxim, Silafluofin, Alphamethrin, Cyfluthrin, C ⁇ ermethrin, Deltamethrin, Permethrin, hnidacloprid, NI-25, Flufenoxuron, Hexaflumuron, Transfluthrin, Trifloxidonidridine, Methiflium dinopridos, Methiflium dinopridos, Thifloxidonidridine, Thifloxidonidridine, Thiflium dinopridos, Thifloxidonidridine, Thiflium dinopridos, Tefluthrin, and fungicides such as epoxyconazole, hexaconazole, azaconazole, propiconazole, tebuconazole, cyproconazole, metconazole, imazalil, dichlorofluoride, tolylflu
• 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.
• heavy metals such as e.g. in bis (trialkyltin) sulfides, tri-w-butylzirmlaurat, tri-butyltin chloride, copper (L) oxide, triethyltin chloride, tri-n-butyl (2-phenyl-4-chlorophenoxy) tin, tributyltin oxide, molybdenum disulfide, Antimony oxide, polymeric butyl titanate, phenyl (bispyridine) bismuth chloride, tri-n-butyltin fluoride, manganese ethylene bisthiocarbamate, zinc dimethyldithiocarbamate, zinc ethylene bisthiocarbamate, zinc and copper salts of 2-pyridinethiol-l-oxydiamide, bisdimoxidylamide (bisdimide) amide, bisdimide amide, -ethylene-bisdithio-c
• the ready-to-use antifouling paints can optionally contain other 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: algicides such as 2-tert-butylamino-4-cyclopropylamino-6-methyltl_io-l, 3,5-triaz_n, dichlorophene, diuron, endothal, fentin acetate, isoproturon, methabenzthiazuron, oxyfluorfen , Quinoclamine and Terbutryn; Fungicides such as Be__zo [ ⁇ ] thiophenecarboxylic acid cyclohexylamide-S, S-dioxide, dichlofluanid, fluorfolpet, 3-iodo-2-propynylbutylcarbamate, tolylfluanid and azoles such as azaconazole, cyproconazole, epoxyconazole, hexaconazole, metazazole, metconazole; Molluscicides such as fentin a
• 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 0.01 to 20% by weight.
• the antifouling agents according to the invention further contain the usual ingredients such as in Ungerer, Chem. Ind. 1985, 37, 730-732 and Williams, Antifouling Marine Coatings, Noyes, Park Ridge, 1973.
• antifoulm 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.'styroVAcryliiitrile 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 vinyl resins.
• Paints may also contain inorganic pigments, organic pigments or dyes, which are preferably insoluble in seawater. Paints may also contain materials, such as rosin, to enable controlled release of the active ingredients. The paints may also contain plasticizers, modifiers affecting theological properties, and other conventional ingredients. The 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 of
• Pests alone or in combination with other active ingredients and auxiliary agents in household insecticide Products are against sensitive and resistant species as well as against all
• Stages of development effective. These pests include:
• Sco ⁇ ionidea e.g. Buthus occitanus.
• Acarina e.g. Argas persicus, Argas reflexus, Bryobia ssp., Dermanyssus gallinae, Glyciphagus domesticus, Omithodoms moubat, Rhipicephalus sanguineus, Trombicula alfreddugesi, Neutrombicula autumnalis, Dermatophagoides pteronissimus, Dermatophagoides forinae.
• Opiliones e.g. Pseudosco ⁇ iones chelifer, Pseudosco ⁇ iones cheiridium, Opiliones phalangium.
• Diplopoda e.g. Blaniulus guttulatus, Polydesmus spp.
• Saltatoria e.g. Acheta domesticus.
• Dermaptera e.g. Forficula auricularia.
• Anopheles spp. Calliphora erythrocephala, Chrysozona pluvialis, Culex quinquefasciatus, Culex pipiens, Culex tarsalis, Drosophila spp., Fannia canicularis, Musca domestica, Phlebotomus spp.,
• Sarcophaga camaria e.g. Achroia grisella, Galleria mellonella, Plodia inte ⁇ unctella,
• Tinea cloacella Tineapellionella, Tineolabisselliella.
• Ctenocephalides canis Ctenocephalides felis, Pulex irritans,
• Hymenoptera for example Camponotus herculeanus, Lasius fuliginosus, Lasius niger, Lasius umbratus, Monomorium pharaonis, Paravespula spp., Tetramorium caespitum.
• anoplura for example Pediculus humanus capitis, Pediculus humanus co ⁇ oris, Phthims pubis.
• the calibration was carried out using 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).
• the lambda max values were determined using the UV spectra from 200 nm to 400 nm in the maxima of the chromatographic signals. Production of starting materials of the formula (HD
• 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 with water to the desired concentration.
• Vessels are filled with sand, active ingredient solution, Meloidogyne z.zcograt ⁇ -egg-L__rven suspension and lettuce seeds.
• the lettuce seeds germinate and the plantlets develop.
• the galls develop at the roots.
• the nematicidal effect is determined in% using the formation of bile. 100% means that no galls were found; 0% means that the number of galls on the treated plants corresponds to that of the untreated control.
• dimethylformamide emulsifier 1.5 parts by weight of dimethylformamide emulsifier: 0.5 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.
• Chinese cabbage leaf slices (Brassica pekinensis), which are affected by all stages of the green peach aphid (Myzus persicae), are sprayed with an active ingredient preparation of the desired concentration.
• the effect is determined in%. 100% means that all aphids have been killed; 0% means that no aphids have been killed.
• dimemylformamide emulsifier 1.5 parts by weight of dimemylformamide emulsifier: 0.5 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.
• Chinese cabbage leaf slices (Brassica pekinensis) are sprayed with an active ingredient preparation of the desired concentration and, after drying, are populated with larvae of the horseradish leaf beetle (Phaedon cochleariae).
• the effect is determined in%. 100% means that all beetle larvae have been killed; 0% means that no beetle larvae have been killed.
• dimethylformamide emulsifier 1.5 parts by weight of dimethylformamide emulsifier: 0.5 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.
• Corn leaf disks (Zea mays) are sprayed with an active ingredient preparation of the desired concentration and, after drying, are covered with caterpillars of the army worm (Spodoptera frugiperda).
• the effect is determined in%. 100% means that all caterpillars have been killed; 0% means that no caterpillar has been killed.
• dimethylformamide emulsifier 1.5 parts by weight of dimethylformamide emulsifier: 0.5 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.
• Bean leaf slices Phaseolus vulgaris
• Triticae Tricholine dexase
• Bean leaf slices Phaseolus vulgaris
• which are affected by all stages of the common spider mite Tetranychus urticae
• an active ingredient preparation of the desired concentration is sprayed with an active ingredient preparation of the desired concentration.
• the effect is determined in%. 100% means that all spider mites have been killed; 0% means that no spider mites have been killed.
• Test animals adults of Ctenocephalides felis
• a suitable active substance solution is prepared from 10 mg active substance with 0.5 ml DMSO. 10 ⁇ l of this formulation are added to 2 ml of citrated cattle blood and stirred.
• Blood drug formulation that can be taken up by the fleas through the parafilm membrane. While the blood is heated to 37 ° C, room temperature is in the area of the flea chambers.
• Controls are mixed with the same volume of DMSO without the addition of a compound.
• Test animals Lucilia cuprina larvae
• Solvent dimethyl sulfoxide
• test tube which contains approx. 1 cm 3 horse meat and 0.5 ml of the active ingredient preparation to be tested. After 48 hours, the effectiveness of the active substance preparation is determined as% larval mortality.
• 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 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
• 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.
• 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 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.

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• Life Sciences & Earth Sciences (AREA)
• Organic Chemistry (AREA)
• Chemical & Material Sciences (AREA)
• Health & Medical Sciences (AREA)
• Plant Pathology (AREA)
• Engineering & Computer Science (AREA)
• Dentistry (AREA)
• General Health & Medical Sciences (AREA)
• Wood Science & Technology (AREA)
• Zoology (AREA)
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• Pest Control & Pesticides (AREA)
• Agronomy & Crop Science (AREA)
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• 2003
  • 2003-12-17 DE DE10359074A patent/DE10359074A1/de not_active Withdrawn
• 2004
  • 2004-12-07 WO PCT/EP2004/013875 patent/WO2005058838A1/de active Application Filing
  • 2004-12-07 CN CNA2004800379328A patent/CN1894218A/zh active Pending
  • 2004-12-07 JP JP2006544274A patent/JP2007514669A/ja not_active Withdrawn
  • 2004-12-07 BR BRPI0417202-7A patent/BRPI0417202A/pt not_active IP Right Cessation
  • 2004-12-07 EP EP04803568A patent/EP1697328A1/de not_active Withdrawn
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