WO2007101546A2 - Combinaisons de principes actifs à propriétés insecticides et acaricides - Google Patents

Combinaisons de principes actifs à propriétés insecticides et acaricides Download PDF

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Publication number
WO2007101546A2
WO2007101546A2 PCT/EP2007/001465 EP2007001465W WO2007101546A2 WO 2007101546 A2 WO2007101546 A2 WO 2007101546A2 EP 2007001465 W EP2007001465 W EP 2007001465W WO 2007101546 A2 WO2007101546 A2 WO 2007101546A2
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Prior art keywords
alkyl
spp
substituted
halogen
alkoxy
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PCT/EP2007/001465
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German (de)
English (en)
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WO2007101546A3 (fr
Inventor
Rüdiger Fischer
Reiner Fischer
Christian Funke
Thomas Bretschneider
Heike Hungenberg
Wolfgang Thielert
Anton Kraus
Hiroshi Kodama
Shingo Tamura
Fumiaki Hakuno
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Bayer Cropscience Ag
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Publication of WO2007101546A2 publication Critical patent/WO2007101546A2/fr
Publication of WO2007101546A3 publication Critical patent/WO2007101546A3/fr

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    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/36—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom five-membered rings
    • A01N43/38—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom five-membered rings condensed with carbocyclic rings
    • 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
    • A01N41/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom
    • A01N41/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom containing a sulfur-to-oxygen double bond
    • A01N41/10—Sulfones; Sulfoxides
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system

Definitions

  • the present invention relates to novel drug combinations which consist of at least one known compound from the class of tetronic or tetramic acids on the one hand and at least one other known active ingredient from the class of phthalic diamides on the other hand and are very suitable for controlling animal pests such as insects and unwanted acarids ,
  • EP-A-0 262 399 and GB-A-2 266 888 disclose similarly structured compounds (3-arylpyrrolidine-2,4-diones), of which, however, no herbicidal, insecticidal or acaricidal action has become known.
  • Unsubstituted, bicyclic 3-arylpyrrolidine-2,4-dione derivatives (EP-A-355 599, EP-A-415 211 and JP-A-12-053 670) are known to have herbicidal, insecticidal or acaricidal activity and substituted monocyclic 3-arylpyrrolidine-2,4-dione derivatives (EP-A-377 893 and EP-A-442 077).
  • EP-A-442 073 polycyclic 3-arylpyrrolidine-2,4-dione derivatives
  • EP-A-456 063 EP-A-521 334, EP-A- 596 298, EP-A-613 884, EP-A-613 885, WO 95/01 997, WO 95/26 954, WO 95/20 572, EP-A-0 668 267, WO 96/25 395, WO 96 / 35,664, WO 97/01 535, WO 97/02 243, WO 97/36868, WO 97/43275, WO 98/05638, WO 98/06721, WO 98/25928, WO 99/16748, WO 99/24437 WO 99/43649, WO 99/48869 and WO 99/55673, WO 01/17972, WO 01/23354, WO 01/74770, WO 03/013249
  • X is halogen, alkyl, alkoxy, haloalkyl, haloalkoxy or cyano
  • W, Y and Z independently of one another represent hydrogen, halogen, alkyl, alkoxy, haloalkyl, haloalkoxy or cyano,
  • A is hydrogen, in each case optionally halogen-substituted alkyl, alkoxyalkyl, saturated, optionally substituted cycloalkyl in which optionally at least one ring atom is replaced by a heteroatom,
  • B is hydrogen or alkyl
  • a and B together with the carbon atom to which they are attached, represent a saturated or unsaturated unsubstituted or substituted cycle, optionally containing at least one heteroatom, D is hydrogen or an optionally substituted radical from the series alkyl,
  • a and D together with the atoms to which they are bonded represent a saturated or unsaturated and optionally at least one heteroatom-containing, unsubstituted or substituted in the A, D-part cycle,
  • G is hydrogen (a) or one of the groups
  • E is a metal ion or an ammonium ion
  • L is oxygen or sulfur
  • M is oxygen or sulfur
  • R! in each case optionally halogen-substituted alkyl, alkenyl, alkoxyalkyl, alkylthioalkyl, polyalkoxyalkyl or optionally substituted by halogen, alkyl or alkoxy-substituted cycloalkyl which may be interrupted by at least one heteroatom, in each case optionally substituted phenyl, phenylalkyl,
  • R 1 is in each case optionally halogen-substituted alkyl, alkenyl, alkoxyalkyl, polyalkoxyalkyl or in each case optionally substituted cycloalkyl,
  • R 1 represents optionally halogen-substituted alkyl or optionally substituted phenyl
  • R 1 and R 5 independently of one another are each optionally halogen-substituted alkyl, alkoxy, alkylamino, dialkylamino, alkylthio, alkenylthio, cycloalkylthio or in each case optionally substituted phenyl, benzyl, phenoxy or phenylthio, and
  • R ⁇ and R ⁇ independently of one another for hydrogen, in each case optionally
  • X 1 is C i -Cg-alkyl, halogen, C y -Cg -alkoxy or Ci-C3-haloalkyl,
  • Y ' is hydrogen, C 1 -C 6 -alkyl, halogen, C 1 -CG-alkoxy, C 1 -C 6 -haloalkyl,
  • Z ' is C 1 -C 6 -alkyl, halogen, C 1 -C 6 -alkoxy,
  • n ' is a number from 0-3,
  • a ' is hydrogen or in each case optionally halogen-substituted straight-chain or branched C 1 -C 12 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkyl, C 1 -C 10 -alkoxy-C 1 -C 6 -alkyl, C 1 -C 4 -alkyl-C 1 -C 4 -alkyl, C 1 -C 1 0-alkylthio-C 2 -C 6 -alkyl, cycloalkyl having 3 to 8 ring atoms, which may be interrupted by oxygen and / or sulfur or in each case optionally by halogen, C 1 - Cg-AIlCyI, C ⁇ Cg haloalkyl, C 1 -CG-AIkOXy-, C 1 - Cg haloalkoxy, nitro-substituted phenyl or phenyl- ⁇ is -CG alkyl
  • a 'and B' together with the carbon atom to which they are attached are saturated or unsaturated, optionally interrupted by oxygen and / or sulfur and optionally substituted by halogen, C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C j - C 1-4 haloalkyl, C 1 -C 4
  • R.1 is in each case optionally halogen-substituted C 1 -C 2 () -alkyl, C 2 -C 20 -alkenyl, C 1 -CG-alkoxy-C 6 -C 6 -alkyl, C 1 -C 6 -alkylthio-C 1 -CG- Alkyl, C ⁇ -Cg-polyalkoxy ⁇ -Cg- alkyl or cycloalkyl having 3-8 ring atoms, which may be interrupted by oxygen and / or sulfur atoms, is,
  • R 2 represents phenoxy-C 1 -C -alkyl optionally substituted by halogen and / or C 1 -C 6 -alkyl
  • R 2 ' is in each case optionally halogen-substituted C 1 -C 2 () -alkyl, C 2 -C 2 ( ) -alkenyl, C 1 -C 6 -alkoxy-C 2 -C 6 -alkyl or C 1 -C 6 -alkoxy-C 1 -C 4 -alkyl
  • R 2 ' is in each case optionally halogen-substituted C 1 -C 2 () -alkyl, C 2 -C 2 ( ) -alkenyl, C 1 -C 6 -alkoxy-C 2 -C 6 -alkyl or C 1 -C 6 -alkoxy-C 1 -C 4 -alkyl
  • halogen is in each case optionally halogen, nitro, C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -halogenoalkyl-substituted phenyl or benzyl,
  • R.3 1 represents optionally substituted by halogen C ⁇ -Cg-alkyl, in each case optionally by Ci-C4-alkyl, halogen, Ci-C4-haloalkyl, Ci-C ⁇ alkoxy, Ci-C4-haloalkoxy, nitro or Cyano is substituted phenyl or benzyl,
  • R4 'and RS' independently of one another in each case optionally halogen-substituted C j -Cg-alkyl, Ci -Cg alkoxy, C j -Cg alkylamino, di (C i -Cg) alkylamino, Ci-Cg-alkylthio, C 2 -C 5 -alkenylthio, C 2 -C 5 -alkynylthio, C 3 -C 5 -cycloalkylthio, in each case optionally by halogen, nitro, cyano, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 1 -C 4 -alkylthio, C 1 -C 4 -alkoxy Halogenoalkylthio, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl-substituted phenyl, phenoxy or pheny
  • Hal is chlorine, bromine or iodine, * denotes a carbon atom in the R or S configuration, preferably in the S configuration,
  • insecticidal and / or acaricidal activity have insecticidal and / or acaricidal activity.
  • insecticidal and / or acaricidal activity of the active compound combinations according to the invention is substantially higher than the sum of the effects of the individual active compounds. So there is an unpredictable, true synergistic effect and not just an effect supplement.
  • the compounds of the formula (I) or (II) can also be present, depending on the nature of the substituents, as geometric and / or optical isomers or mixtures of isomers in different compositions, which can optionally be separated in a customary manner , Both the pure isomers and the mixtures of isomers, their preparation and use and agents containing them are the subject of the present invention. In the following, however, for the sake of simplicity, reference is always made to compounds of the formula (I) or (EQ), although both the pure compounds and, if appropriate, mixtures with different proportions of isomeric compounds are meant.
  • W is preferably hydrogen, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, chlorine, bromine or fluorine,
  • X is preferably C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkyl, fluorine, chlorine or bromine,
  • Y and Z independently of one another are preferably hydrogen, C 1 -C 4 -alkyl, halogen, C 1 -C 4 -alkoxy or C 1 -C 4 -haloalkyl,
  • A is preferably hydrogen or in each case optionally halogen-substituted C 1 -C 6 -alkyl or C 3 -C 9 -cycloalkyl,
  • B is preferably hydrogen, methyl or ethyl
  • A, B and the carbon atom to which they are attached are preferably saturated CyC 6 -cycloalkyl, in which optionally one ring member is replaced by oxygen or sulfur and which is optionally mono- or disubstituted by C 1 -C 4 -alkyl, trifluoromethyl or C 1 -C 4 -alkyl 4- alkoxy is substituted,
  • D is preferably hydrogen, in each case optionally fluorine- or chlorine-substituted C 1 -C 6 -alkyl, C 3 -C 4 -alkenyl or C 3 -C 6 -cycloalkyl,
  • a and D together preferably represent optionally methyl-substituted C 3 -C 4 -alkanediyl, in which optionally a methylene group is replaced by sulfur,
  • G is preferably hydrogen (a) or one of the groups
  • E is a metal ion or an ammonium ion
  • M is oxygen or sulfur
  • R 1 preferably represents in each case optionally halogen-substituted C r Ci 0 alkyl, C2 - Cio-alkenyl, Ci-C4-alkoxy-Ci-C 4 alkyl, C r C 4 alkylthio-Ci-C 4 - C 3 -C 6 -cycloalkyl optionally substituted by fluorine, chlorine, C 1 -C 4 -alkyl or C 1 -C 2 -alkoxy,
  • Triflourmethyl Triflourmethoxy substituted phenyl is optionally substituted by fluorine, chlorine, bromine, cyano, nitro, Ci-C 4 alkyl, C r C 4 alkoxy, or Triflourmethyl Triflourmethoxy substituted phenyl,
  • R 2 preferably represents in each case optionally substituted by fluorine or chlorine, Ci-Ci 0 - alkyl, C 2 -C 10 alkenyl, C r C 4 -alkoxy-C 2 -C 4 alkyl,
  • R 3 is preferably C 1 -C 4 -alkyl optionally substituted by fluorine or phenyl optionally substituted by fluorine, chlorine, bromine, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, trifluoromethyl, trifluoromethoxy, cyano or nitro,
  • R 4 preferably independently represent in each case optionally substituted by fluorine or chlorine, Ci-C4-alkyl, Ci-C 4 alkoxy, Ci-C 4 alkylamino, C] -C 4 -alkylthio or represents in each case optionally fluorine-, chlorine , Bromine, nitro, cyano, QC 4 -alkoxy,
  • R 5 is preferably C 1 -C 4 -alkoxy or C 1 -C 4 -thioalkyl
  • R 6 is preferably C 1 -C 6 -alkyl, C 3 -C 6 -cycloalkyl, C 1 -C 6 -alkoxy, C 3 -C 6 -alkenyl, C 1 -C 4 -alkoxy-C r C 4 - alkyl,
  • R 7 is preferably C 1 -C 6 -alkyl, C 3 -C 6 -alkenyl or C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl,
  • R 6 and R 7 together preferably represent an optionally substituted by methyl or ethyl C 3 -C 6 alkylene, in which optionally a carbon atom is replaced by oxygen or sulfur
  • W is particularly preferably hydrogen, methyl, ethyl, chlorine, bromine or methoxy
  • X is particularly preferably chlorine, bromine, methyl, ethyl, propyl, isopropyl, methoxy, ethoxy or trifluoromethyl,
  • Y and Z are more preferably independently of one another hydrogen, fluorine, chlorine, bromine, methyl, ethyl, propyl, isopropyl, trifluoromethyl or methoxy,
  • B is particularly preferably hydrogen, methyl or ethyl
  • A, B and the carbon atom to which they are attached are particularly preferably saturated C 6 -cycloalkyl, in which optionally one ring member is replaced by oxygen and which is optionally monosubstituted by methyl, ethyl, methoxy, ethoxy, propoxy or butoxy,
  • D is particularly preferably hydrogen, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, allyl, cyclopropyl, cyclopentyl or cyclohexyl,
  • a and D together are particularly preferably C 3 -C 4 -alkanediyl optionally substituted by methyl,
  • G is particularly preferably hydrogen (a) or one of the groups
  • M is oxygen or sulfur
  • R 1 particularly preferably represents C 1 -C 8 -alkyl, C 2 -C 4 -alkenyl, methoxymethyl, ethoxymethyl, ethylthiomethyl, cyclopropyl, cyclopentyl or cyclohexyl,
  • R 2 particularly preferably represents C 1 -C 8 -alkyl, C 2 -C 4 -alkenyl, methoxyethyl, ethoxyethyl or phenyl or benzyl,
  • R 6 and R 7 independently of one another particularly preferably represent methyl, ethyl or together represent a C 5 -alkylene radical in which the C 3 -methylene group is replaced by oxygen
  • active compound combinations comprising compounds of the formula (I) in which the radicals have the following meaning: W is very particularly preferably hydrogen or methyl,
  • X very particularly preferably represents chlorine, bromine or methyl
  • Y and Z are very particularly preferably each independently hydrogen, chlorine, bromine or methyl
  • A, B and the carbon atom to which they are attached very particularly preferably represent saturated C 6 -cycloalkyl in which optionally one ring member is replaced by oxygen and which is optionally monosubstituted by methyl, methoxy, ethoxy, propoxy or butoxy,
  • D is very particularly preferably hydrogen
  • G is very particularly preferably hydrogen (a) or one of the groups
  • M is oxygen or sulfur
  • R 1 very particularly preferably represents C 1 -C 8 -alkyl, C 2 -C 4 -alkenyl, methoxymethyl, ethoxymethyl, ethylmethylthio, cyclopropyl, cyclopentyl, cyclohexyl or optionally just by fluorine, chlorine, bromine, methyl, methoxy, trifluoromethyl,
  • R 2 very particularly preferably represents C 1 -C 8 -alkyl, C 2 -C 4 -alkenyl, methoxyethyl, ethoxyethyl, phenyl or benzyl,
  • R 6 and R 7 independently of one another very particularly preferably represent methyl, ethyl or together represent a C 5 -alkylene radical in which the C 3 -methylene group has been replaced by oxygen.
  • X 1 is C 1 -C 4 -alkyl, chlorine, bromine, C 1 -C 4 -alkoxy or C 1 -C 6 -haloalkyl,
  • Y 1 is hydrogen, C 1 -C 4 -alkyl, fluorine, chlorine, bromine, C 1 -C 4 -alkoxy, C 1 -C 3 -haloalkyl,
  • Z 1 is C 1 -C 4 -alkyl, chlorine, bromine, C 1 -C 4 -alkoxy,
  • n 1 is a number from 0-2,
  • a ' is hydrogen or in each case optionally mono- to trisubstituted by fluorine-substituted straight-chain or branched C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 1 -C 4 -alkoxy-C 1 -C 2 -alkyl,
  • Cycloalkyl having 3-8 ring atoms which may optionally be interrupted by oxygen and / or sulfur or represents optionally mono- to disubstituted by fluorine, chlorine, bromine, Ci-C2-alkyl, Q ⁇ haloalkyl, C j ⁇ alkoxy, C j ⁇ haloalkoxy, nitro-substituted phenyl or benzyl, B 'is hydrogen, C 1 -C 2 -alkyl or C j -C 2 -alkoxy-C 1 -C 2 -alkyl
  • a 'and B' together with the carbon atom to which they are bonded are a saturated or unsaturated, optionally interrupted by oxygen and / or sulfur and optionally mono- to disubstituted by fluorine, chlorine, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, Ci-C2-haloalkyl, Ci-C2-haloalkoxy or Ci-C2-alkylthio substituted 3- to 7-membered ring form,
  • R.1 is in each case optionally mono- to trisubstituted by fluorine or chlorine-substituted C 1 -C 16 -alkyl, C 2 -C 16 -alkenyl, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, C 1 -C 4 -alkylthio-C 1 -C 4 -alkyl, C 4 alkyl or cycloalkyl having 3-6 ring atoms which may be interrupted by oxygen and / or sulfur atoms,
  • J R ⁇ represents in each case optionally mono- to pentasubstituted by fluorine or chlorine by-substituted C - C2o alkyl, C2-C20 "alkenyl, Ci-Cg-alkoxy ⁇ -Ce-alkyl, Ci-C6-polyalkoxy-C2-Cg-alkyl represents . each optionally optionally mono- to disubstituted by fluorine, chlorine, bromine, nitro, C ⁇ -Cg-alkyl, C ⁇ -Cg-alkoxy, Ci-C4-haloalkyl-substituted phenyl or benzyl,
  • R ⁇ for optionally mono- to trisubstituted by fluorine or chlorine-substituted Ci-C4-alkyl, each optionally optionally once or twice by C j -C ⁇ alkyl, fluorine, chlorine, bromine, Ci-C ⁇ haloalkyl, C ⁇ -C ⁇ Alkoxy, Cj-C4-haloalkoxy, nitro or cyano substituted phenyl or benzyl,
  • R ⁇ and R ⁇ independently of one another in each case optionally monosubstituted to trisubstituted by fluorine or chlorine, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -alkylamino, di- (C ⁇ -C 4) -alkylamino, C 1 -C 4 Alkylthio, C 2 -C 4 -alkenylthio, C 3 -C 6 -cycloalkylthio, in each case optionally mono- to disubstituted by fluorine, chlorine, bromine, nitro, cyano, C 1 -C 2
  • Rr and R 'independently of one another are each optionally mono- to trisubstituted by fluorine or chlorine-substituted Ci-Cg-alkyl, C ⁇ -Cg-alkoxy, Cß-Cg-alkenyl, Ci-C4-alkoxy-Cj-C2-alkyl, optionally simply up to twice by fluorine, chlorine, bromine, C1-C2-
  • halogen is preferably chlorine and fluorine.
  • X ' is C 1 -C 4 -alkyl, chlorine, bromine, C 1 -C 4 -alkoxy or trifluoromethyl,
  • Y ' is hydrogen, C 1 -C 4 -alkyl, chlorine, bromine, C 1 -C 4 -alkoxy, C 1 -C 2 -haloalkyl,
  • Z ' is C 1 -C 4 -alkyl, chlorine, bromine, C j -C 4 -alkoxy,
  • n 1 is 0 or 1
  • a 'and B' are saturated by C ⁇ -C 4 alkyl or C j -C 4 alkoxy substituted 5- to 6-glie- drigen ring which is optionally mono-, together with the carbon atom to which they are attached, G 'for hydrogen (a) or for the groups
  • RI ' is in each case optionally monosubstituted to trisubstituted by fluorine or chlorine, C 1 -C 12 -alkyl, C 2 -C 12 -alkenyl, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, or cycloalkyl having 3 to 6
  • Ring atoms which may be interrupted by 1 to 2 oxygen atoms,
  • R 2 ' is C 1 -C 12 -alkyl, C 2 -C- ⁇ 2 -alkenyl, C ⁇ -C 4 -alkoxy-C 2 -C 4 -alkyl,
  • X ' is methyl, ethyl, chlorine, bromine, methoxy, ethoxy or trifluoromethyl
  • Y ' is hydrogen, methyl, ethyl, chlorine, bromine, methoxy or trifluoromethyl
  • Z ' is methyl, ethyl, chlorine, bromine or methoxy
  • n 1 is 0 or 1
  • a 'and B' together with the carbon atom to which they are attached form a saturated 5- to 6-membered ring which is optionally substituted by methyl, ethyl, propyl, methoxy, ethoxy, propoxy, butoxy or isobutoxy,
  • R.1 is in each case optionally mono- to trisubstituted by fluorine or chlorine, C 1 -C 6 -alkyl, C 2 -C -alkenyl, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, or cycloalkyl having 3 to 6 ring atoms, which is substituted by 1 to 2 oxygen atoms can be interrupted, stands,
  • R 2 is Ci-Cg-alkyl, C2-Cg-alkenyl, Ci-C ⁇ alkoxy ⁇ -Cß-alkyl,
  • mixtures comprising at least one of the compounds (IIa), (IIIb) or (IIIc).
  • IIHa (S) -S-IOd-N 1 - ⁇ 2-methyl-4- [1,2,2,2-tetrafluoro-1 - (trifluoromethyl) ethyl] phenyl ⁇ -N 2 - (1-methyl -2-methylsulfonylethyl) phthalamide
  • the active compound combinations according to the invention contain, in addition to at least one active compound of the formula (III) in enantiomerically pure form or as a mixture of the two enantiomers in any ratio, at least one compound of the formula (I) and / or of the formula (II).
  • the active compound combinations according to the invention preferably contain one of the active compounds (HIa), (HIb) or (lue) and a compound of the formula (I) or a compound of the formula (II).
  • Particularly preferred is a mixture containing the compound (DIb) and the compound (I-c-2).
  • the combinations according to the invention contain an active ingredient of the formula (I) or an active ingredient of the formula (II) and an active ingredient of the formula (II) in the following preferred and particularly preferred mixing ratios:
  • Particularly preferred mixing ratio 25: 1 to 1:25
  • the mixing ratios are based on weight ratios.
  • the ratio is to be understood as active compound of the formula (I) or active compound of the formula (II): active compound of the formula (III).
  • the active compound combinations according to the invention are suitable for good plant tolerance, favorable toxicity to warm-blooded animals and good environmental compatibility for the protection of plants and plant organs, for increasing crop yields, improving the quality of the crop and for controlling animal pests, in particular insects, arachnids, helminths, nematodes and mollusks in agriculture, horticulture, livestock, forests, gardens and recreational facilities, in the protection of materials and materials and in the hygiene sector. They can preferably be used as crop protection agents. They are effective against normally sensitive and resistant species as well as against all or individual stages of development.
  • the above mentioned pests include:
  • Anoplura e.g. Damalinia spp., Haematopinus spp., Linognathus spp., Pediculus spp., Trichodectes spp.
  • Epitrimerus pyri Eutetranychus spp., Eriophyes spp., Hemitarsonemus spp., Hyalomma spp., Ixodes spp., Latrodectus mactans, Metatetranychus spp., Oligonychus spp., Ornithodoros spp., Panonychus spp., Phyllocoptruta oleivora, Polyphagotarsonemus latus, Psoroptes spp., Rhipicephalus spp., Rhizoglyphus spp., Sarcoptes spp., Scorpio maurus, Stenotarsonemus spp., Tarsonemus spp., Tetranychus spp., Vasates lycopersici.
  • Ceuthorhynchus spp. Ceuthorhynchus spp., Cleonus mendicus, Conoderus spp., Cosmopolites spp., Costelytra zealandica, Curculio spp., Cryptorhynchus lapathi, Dermestes spp., Diabrotica spp., Epilachna spp., Faustinus cubae, Gibbium psylloides, Heteronychus arator, Hylamorpha elegans, Hylotrupes bajulus, Hypera postica, Hypothenemus spp., Lachnosterna consanguinea, Leptinotarsa decemlineata, Lissorhoptrus oryzophilus, Lixus spp., Lyctus spp., Meligethes aeneus, Melolontha melolontha, Migdolus spp., Mono
  • Gastropoda eg Arion spp., Biomphalaria spp., Bulinus spp., Deroceras spp., Galba spp., Lymnaea spp., Oncomelania spp., Succinea spp.
  • helminths from the class of helminths, for example, Ancylostoma duodenale, Ancylostoma ceylanicum, Acylostoma braziliensis, Ancylostoma spp., Ascaris lubricoides, Ascaris spp., Brugia malayi, Brugia timori, Bunostomum spp., Chabertia spp., Clonorchis spp., Cooperia spp., Dicrocoelium spp , Dictyocaulus filaria, Diphyllobothrium latum, Dracunculus medinensis, Echinococcus granulosus, Echinococcus multilocularis, Enterobius vermicularis, Faciola spp., Haemonchus spp., Heterakis spp., Hymenolepis nana, Hyostrongulus spp., Lo
  • protozoa such as Eimeria
  • Eimeria protozoa
  • Heliopeltis spp. Horcias nobilellus, Leptocorisa spp., Leptoglossus phyllopus, Lygus spp., Macropes excavatus, Miridae, Nezara spp., Oebalus spp., Pentomidae, Piesma quadrata, Piezodorus spp., Psallus seriatus, Pseudacysta persea, Rhodnius spp. Sahlbergella singularis, Scotinophora spp., Stephanitis nashi, Tibraca spp., Triatoma spp.
  • Hymenoptera e.g. Diprion spp., Hoplocampa spp., Lasius spp., Monomorium pharaonis, Vespa spp.
  • Pseudoplusia includens, Pyrausta nubilalis, Spodoptera spp., Thermesia gemmatalis, Tinea pellionella, Tineola bisselliella, Tortrix viridana, Trichoplusia spp.
  • Orthoptera e.g. Acheta domesticus, Blatta orientalis, Blattella germanica, Gryllotalpa spp., Leucophaea maderae, Locusta spp., Melanoplus spp., Periplaneta americana, Schistocerca gregaria.
  • siphonaptera e.g. Ceratophyllus spp., Xenopsylla cheopis.
  • Symphyla e.g. Scutigerella immaculata.
  • Thysanoptera eg Basothrips biformis, Enneothrips flavens, Frankliniella spp., Heliothrips spp., Hercinothrips femoralis, Kakothrips spp., Rhipiphorothrips cruentatus, Scirtothrips spp., Taeniothrips cardamoni, Thrips spp. From the order of Thysanura eg Lepisma saccharina.
  • the plant parasitic nematodes include e.g. Anguina spp., Aphelenchoides spp., Belonoaimus spp., Bursaphelenchus spp., Ditylenchus dipsaci, Globodera spp., Heliocotylenchus spp., Heterodera spp., Longidorus spp., Meloidogyne spp., Pratylenchus spp., Radopholus similis, Rotylenchus spp. Trichodorus spp., Tylenchorhynchus spp., Tylenchulus spp., Tylenchulus semipenetrans, Xiphinema spp.
  • Anguina spp. Aphelenchoides spp., Belonoaimus spp., Bursaphelenchus spp., Ditylenchus dipsaci, Globodera
  • the active compound combinations according to the invention may optionally also be used in certain concentrations or application rates as herbicides, safeners, growth regulators or agents for improving plant properties, or as microbicides, for example as fungicides, antimycotics, bactericides, viricides (including anti-viral agents) or as anti-MLO agents ( Mycoplasma-like-organism) and RLO (Rickettsia-like-organism). If appropriate, they can also be used as intermediates or precursors for the synthesis of further active ingredients.
  • the active compound combinations according to the invention may optionally also be used in certain concentrations or application rates with at least one herbicide, safener, waxy regulator or plant properties improver, or with at least one microbicide, for example fungicide, antimycotic, bactericide, viricide (including anti-viral agents) or with agents against MLO (Mycoplasma-like-organism) and RLO (Rickettsia-like-organism) or mixtures thereof.
  • at least one herbicide, safener, waxy regulator or plant properties improver or with at least one microbicide, for example fungicide, antimycotic, bactericide, viricide (including anti-viral agents) or with agents against MLO (Mycoplasma-like-organism) and RLO (Rickettsia-like-organism) or mixtures thereof.
  • plants are understood as meaning all plants and plant populations, such as desired and undesired wild plants or crop plants (including naturally occurring crop plants).
  • Crop plants can be plants which can be obtained by conventional breeding and optimization methods or by biotechnological and genetic engineering methods or combinations of these methods, including the transgenic plants and including the plant varieties which can or can not be protected by plant breeders' rights.
  • Plant parts are to be understood as meaning all aboveground and underground parts and organs of the plants, such as shoot, leaf, flower and root, examples of which include 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, such as cuttings, tubers, rhizomes, offshoots and seeds.
  • the treatment according to the invention of the plants and plant parts with the active substance combinations takes place directly or by acting on their environment, habitat or storage space according to the customary treatment methods, eg by dipping, spraying, evaporating, atomizing, spreading, spreading, injecting and in propagation material, in particular in seed, furthermore by single or multi-layer wrapping.
  • the active compound combinations can be converted into the customary formulations, such as solutions, emulsions, wettable powders, water- and oil-based suspensions, powders, dusts, pastes, soluble powders, soluble granules, scattering granules, suspension-emulsion concentrates, active substance-impregnated natural products, active ingredient Impregnated synthetic materials, fertilizers and Feinstverkapselitch in polymeric materials.
  • customary formulations such as solutions, emulsions, wettable powders, water- and oil-based suspensions, powders, dusts, pastes, soluble powders, soluble granules, scattering granules, suspension-emulsion concentrates, active substance-impregnated natural products, active ingredient Impregnated synthetic materials, fertilizers and Feinstverkapselitch in polymeric materials.
  • formulations are prepared in a known manner, e.g. by mixing the active compounds with extenders, ie liquid solvents and / or solid carriers, if appropriate using surface-active agents, ie emulsifiers and / or dispersants and / or foam-forming agents.
  • extenders ie liquid solvents and / or solid carriers
  • surface-active agents ie emulsifiers and / or dispersants and / or foam-forming agents.
  • Excipients which can be used are those which are suitable for imparting special properties to the composition itself and / or preparations derived therefrom (for example spray liquor, seed dressing), such as certain technical properties and / or specific biological properties.
  • Typical auxiliaries are: extenders, solvents and carriers.
  • polar and non-polar organic chemical liquids e.g. from the classes of aromatic and non-aromatic hydrocarbons (such as paraffins, alkylbenzenes, alkylnaphthalenes, chlorobenzenes), alcohols and polyols (which may also be substituted, etherified and / or esterified), ketones (such as acetone, cyclohexanone), Esters (also fats and oils) and (poly) ethers, the simple and substituted amines, amides, lactams (such as N-alkylpyrrolidones) and lactones, the sulfones and sulfoxides (such as dimethylsulfoxide).
  • aromatic and non-aromatic hydrocarbons such as paraffins, alkylbenzenes, alkylnaphthalenes, chlorobenzenes
  • alcohols and polyols which may also be substituted, etherified and / or esterified
  • ketones
  • organic solvents can also be used as auxiliary solvents.
  • Suitable liquid solvents are essentially: aromatics, such as xylene, toluene, or alkylnaphthalenes, chlorinated aromatics and chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chloroethylenes or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, for example petroleum fractions, mineral acids.
  • Suitable solid carriers are:
  • Ammonium salts and ground natural minerals such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, and ground synthetic minerals, such as fumed silica, alumina and silicates, as solid carriers for granules are suitable: e.g. crushed and fractionated natural rocks such as calcite, marble, pumice, sepiolite, dolomite and synthetic granules of inorganic and organic flours and granules of organic material such as paper, sawdust, coconut shells, corn cobs and tobacco stalks; suitable emulsifiers and / or foam formers are: e.g.
  • nonionic and anionic emulsifiers such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, e.g. Alkylaryl polyglycol ethers, alkylsulfonates, alkyl sulfates, arylsulfonates and protein hydrolysates;
  • suitable dispersants are non-ionic and / or ionic substances, e.g.
  • Adhesives such as carboxymethylcellulose, natural and synthetic powdery, granular or latex-type polymers such as gum arabic, polyvinyl alcohol, polyvinyl acetate, and natural phospholipids such as cephalins and lecithins and synthetic phospholipids may be used in the formulations.
  • Dyes such as inorganic pigments such as 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.
  • Other additives may be fragrances, mineral or vegetable optionally modified oils, waxes and nutrients (also trace nutrients), such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.
  • Stabilizers such as cold stabilizers, preservatives, antioxidants, light stabilizers or other chemical and / or physical stability-improving agents may also be present.
  • the formulations generally contain between 0.01 and 98% by weight of active ingredient, preferably between 0.5 and 90%.
  • the active compound combinations according to the invention can be present in commercial formulations as well as in the formulations prepared from these formulations in admixture 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 esters, chlorinated hydrocarbons, phenylureas, microorganism-produced substances and the like.
  • the active compound combinations according to the invention may also be present when used as insecticides in their commercial formulations as well as in the formulations prepared from these formulations in admixture with synergists.
  • Synergists are compounds that increase the effect of the active ingredients without the added synergist itself having to be active.
  • the active substance content of the application forms prepared from the commercial formulations can vary within wide ranges.
  • the active ingredient concentration of the use forms may be from 0.00000001 up to 95% by weight of active compound, preferably between 0.00001 and 1% by weight.
  • the application is done in a custom forms adapted to the application forms.
  • plants and their parts can be treated.
  • wild-type or plant species obtained by conventional biological breeding methods such as crossing or protoplast fusion
  • plant cultivars and their parts are treated.
  • transgenic plants and plant cultivars obtained by genetic engineering are obtained (Genetically Modified Organisms) and their parts.
  • the terms "parts” or “parts of plants” or “plant parts” have been explained above.
  • Plant varieties are understood as meaning plants having new traits which have been bred by conventional breeding, by mutagenesis or by recombinant DNA techniques. These can be varieties, biotypes and genotypes.
  • the treatment according to the invention may also give rise to superadditive ("synergistic") effects.
  • superadditive for example, reduced application rates and / or extensions of the spectrum of action and / or an increase in the effect of the substances and agents usable in the invention, better plant growth, increased tolerance to high or low temperatures, increased tolerance to drought or to water or soil salt content, increased flowering power facilitated harvest, acceleration of ripeness, higher crop yields, higher quality and / or higher nutritional value of the harvested products, higher shelf life and / or machinability of the harvested products, which exceed the actual expected effects.
  • the preferred plants or plant varieties to be treated according to the invention to be treated include all plants which, as a result of the genetic engineering modification, obtained genetic material which gives these plants particularly advantageous valuable properties ("traits").
  • traits are better plant growth, increased tolerance to high or low temperatures, increased tolerance to dryness or to bottoms salt, increased flowering, 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.
  • Further and particularly emphasized examples of such properties are an increased defense of the plants against animal and microbial pests, as against insects, mites, phytopathogenic fungi, bacteria and / or viruses as well as an increased tolerance of the plants against certain herbicidal active substances.
  • transgenic plants are the important crops such as cereals (wheat, rice), corn, soybeans, potatoes, sugar beets, tomatoes, peas and other vegetables, cotton, tobacco, oilseed rape and fruit plants (with the fruits apples, pears, citrus fruits and Grapes), with special emphasis on maize, soya, potato, cotton, tobacco and oilseed rape.
  • Traits that are particularly emphasized are the increased defense of the plants against insects, arachnids, Nematodes and snails by toxins produced in the plants, in particular those produced by the genetic material from Bacillus thuringiensis (eg by the genes Cry ⁇ A (a), CryIA (b), Cry ⁇ A (c), CryllA, CrylEA, CryIIIB2, Cry9c Cry2Ab, Cry3Bb and CryEF and their combinations) in the plants (hereinafter "Bt plants”). Traits also highlight the increased resistance of plants to fungi, bacteria and viruses by systemic acquired resistance (SAR), systemin, phytoalexins, elicitors and resistance genes and correspondingly expressed proteins and toxins.
  • SAR systemic acquired resistance
  • Traits which are furthermore particularly emphasized are the increased tolerance of the plants to certain herbicidally active compounds, for example imidazolinones, sulfonylureas, glyphosate or phosphinotricin (eg "PAT" gene).
  • the genes which confer the desired properties (“traits") can also occur in combinations with one another in the transgenic plants.
  • Examples of “Bt plants” are maize varieties, cotton varieties, soybean varieties and potato varieties which are sold under the trade names YIELD GARD® (eg corn, cotton, soya), KnockOut® (eg maize), StarLink® (eg maize), Bollgard® ( Cotton), Nucotn® (cotton) and NewLeaf® (potato).
  • herbicide-tolerant plants are maize varieties, cotton varieties and soybean varieties, which are sold under the trade names Roundup Ready® (tolerance to glyphosate eg corn, cotton, soy), Liberty Link® (tolerance to phosphinotricin, eg rapeseed), IMI® (tolerance against imidazolinone) and STS® (tolerance to sulfonylureas eg corn).
  • Roundup Ready® tolerance to glyphosate eg corn, cotton, soy
  • Liberty Link® tolerance to phosphinotricin, eg rapeseed
  • IMI® tolerance against imidazolinone
  • STS® tolerance to sulfonylureas eg corn
  • Clearf ⁇ eld® varieties eg corn
  • the listed plants can be treated particularly advantageously with the active compound combinations according to the invention.
  • the preferred ranges given above for the active substance combinations also apply to the treatment of these plants.
  • Particularly emphasized is the plant treatment with the active ingredient combinations specifically mentioned in the present text.
  • the active compound combinations according to the invention not only act against plant, hygiene and storage pests, but also in the veterinary sector against animal parasites (ecto- and endoparasites) such as ticks, leather ticks, mange mites, running mites, flies (stinging and licking), parasitic fly larvae, lice , Hair pieces, featherlings and fleas.
  • animal parasites ecto- and endoparasites
  • ecto- and endoparasites such as ticks, leather ticks, mange mites, running mites, flies (stinging and licking), parasitic fly larvae, lice , Hair pieces, featherlings and fleas.
  • parasites include: From the order of the Anoplurida eg Haematopinus spp., Linognathus spp., Pediculus spp., Phtirus spp., Solenopotes spp.
  • 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 i., Culicoides spp., Chrysops spp., Hybomitra spp., Atylotus spp., Tabanus spp.
  • Haematopota spp. Philipomyia spp., Braula spp., Musca spp., Hydrotaea spp., Stomoxys spp., Haematobia spp., Morellia spp., Fannia spp., Glossina spp., Calliphora spp., Lucilia spp., Chrysomyia Spp., Wohlfahrtia spp., Sarcophaga spp., Oestrus spp., Hypoderma spp., Gasterophilus spp., Hippobosca spp., Lipoptena spp., Melophagus spp.
  • siphonaptrida e.g. Pulex spp., Ctenocephalides spp., Xenopsylla spp., Ceratophyllus spp.
  • heteropterid e.g. Cimex spp., Triatoma spp., Rhodnius spp., Panstrongylus 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., Knemidocoptes spp., Cytodites spp., Laminosioptes spp.
  • the active compound combinations according to the invention are also suitable for controlling
  • Arthropods the farm animals, such as cattle, sheep, goats, horses, pigs, donkeys, camels, buffaloes, rabbits, chickens, turkeys, ducks, geese, bees, other pets such as dogs, cats, caged birds, aquarium fish and so-called experimental animals , such as Hamsters, guinea pigs, rats and mice.
  • the application of the active compound combinations according to the invention takes place in the veterinary sector and in animal husbandry in a known manner by enteral administration in the form of, for example, tablets, capsules, infusions, drenches, granules, pastes, boilies, the feed-through process, suppositories, by parenteral administration, as 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, pouring (pour-on and spot-on ), washing, powdering and with the aid of active substance-containing moldings, such as collars, ear tags, tail marks, limb bands, holsters, marking devices, etc.
  • enteral administration in the form of, for example, tablets, capsules, infusions, drenches, granules, pastes, boilies, the feed-through process, suppositories
  • parenteral administration as by injections (
  • the active ingredient combinations When used for livestock, poultry, pets, etc., the active ingredient combinations may be used as formulations (for example, powders, emulsions, flowables) containing the active ingredients in an amount of 1 to 80% by weight, directly or after 100 to 10,000 dilution or use as a chemical bath.
  • formulations for example, powders, emulsions, flowables
  • the active compound combinations according to the invention have a high insecticidal activity against insects which destroy industrial materials.
  • insects By way of example and preferably without limiting however, the following insects are mentioned:
  • Hymenoptera such as Sirex juvencus, Urocerus gigas, Urocerus gigas taignus, Urocerus augur;
  • Termites such as Kalotermes flavicollis, Cryptotermes brevis, Heterotermes indicola, Reticulitermes flavipes, Reticulitermes santonensis, Reticulitermes lucifugus, Mastotermes darwiniensis, Zootermopsis nevadensis, Coptotermes formosanus;
  • Bristle tails like Lepisma saccharina.
  • Technical materials in the present context are non-living materials, such as preferably plastics, adhesives, glues, papers and cardboard, leather, wood, wood processing products and paints.
  • the ready-to-use agents may optionally contain further insecticides and, if appropriate, one or more fungicides.
  • the active compound combinations according to the invention can be used to protect against fouling of objects, in particular of hulls, sieves, nets, structures, quays and signal systems, which come into contact with seawater or brackish water.
  • active compound combinations according to the invention can be used alone or in combinations with other active substances as antifouling agents.
  • the active ingredient combinations are also suitable for controlling animal pests in household, hygiene and storage protection, in particular of insects, arachnids and mites, which are used in closed rooms, such as apartments, factory buildings, offices, vehicle cabins u.a. occurrence. They can be used to control these pests, alone or in combination with other active ingredients and adjuvants in household insecticide products. They are effective against sensitive and resistant species and against all stages of development. These pests include:
  • Acarina e.g. Argas persicus, Argas reflexus, Bryobia ssp., Dermanyssus gallinae, Glyciphagus domesticus, Ornithodorus moubat, Rhipicephalus sanguineus, Trombicula alfreddugesi, Neutrombicula autumnalis, Dermatophagoides pteronissimus, Dermatophagoides forinae.
  • Opiliones e.g. Pseudoscorpiones chelifer, Pseudoscorpiones cheiridium, Opiliones phalangium.
  • Zygentoma e.g. Ctenolepisma spp., Lepisma saccharina, Lepismodes inquilinus.
  • Diptera e.g. Aedes aegypti, Aedes albopictus, Aedes taeniorhynchus, Anopheles spp., Calliphora erythrocephala, Chrysozona pluvialis, Culex quinquefasciatus, Culex pipiens, Culex tarsalis, Drosophila spp., Fannia canicularis, Musca domestica, Phlebotomus spp., Sarcophaga carnaria, Simulium spp., Stomoxys Calcitrans, Tipula paludosa.
  • Lepidoptera e.g. Achroia grisella, Galleria mellonella, Plodia interpunctella, Tinea cloacella, Tinea pellionella, Tineola bisselliella.
  • Ctenocephalides canis Ctenocephalides felis, Pulex irritans, Tunga penetrans, Xenopsylla cheopis.
  • Hymenoptera e.g. Camponotus herculeanus, Lasius fuliginosus, Lasius niger, Lasius umbratus, Monomorium pharaonis, Paravespula spp., Tetramorium caespitum.
  • Application is in aerosols, non-pressurized sprays, e.g. Pump and atomizer sprays, fog machines, foggers, foams, gels, evaporator products with cellulose or plastic evaporator plates, liquid evaporators, gel and membrane evaporators, propeller driven evaporators, energyless or passive evaporation systems, moth papers, moth cakes and moth gels, as granules or dusts, in litter or bait stations.
  • Pump and atomizer sprays e.g. Pump and atomizer sprays, fog machines, foggers, foams, gels, evaporator products with cellulose or plastic evaporator plates, liquid evaporators, gel and membrane evaporators, propeller driven evaporators, energyless or passive evaporation systems, moth papers, moth cakes and moth gels, as granules or dusts, in litter or bait stations.
  • a synergistic effect is always present in insecticides and acaricides whenever the effect of the active ingredient combinations is greater than the sum of the effects of the individually applied active ingredients.
  • X means the degree of killing, expressed in% of the untreated control, when using the active substance A at a rate of m g / ha or in a concentration of m ppm,
  • Y means the degree of killing, expressed in% of the untreated control, when using the active ingredient B in an application rate of n g / ha or in a concentration of n ppm
  • Active substances A and B in amounts of m and n g / ha or in a concentration of m and n ppm,
  • Emulsifier 2 parts by weight of alkylaryl polyglycol ether
  • active compound 1 part by weight of active compound is mixed with the indicated amounts of solvent and emulsifier, and the concentrate is diluted with emulsifier-containing water to the desired concentration.
  • Cotton leaves (Gossypium herbaceum), which are heavily infested by the cotton aphid ⁇ Aphis gossypii), are treated by being dipped into the preparation of active compound of the desired concentration.
  • the kill is determined in%. 100% means that all aphids have been killed; 0% means that no aphids have been killed.
  • the determined kill values are calculated according to the Colby formula (see page 1).
  • Emulsifier 2 parts by weight of alkylaryl polyglycol ether
  • active compound 1 part by weight of active compound is mixed with the indicated amounts of solvent and emulsifier, and the concentrate is diluted with emulsifier-containing water to the desired concentration.
  • Cabbage leaves (Brassica olerace ⁇ ) which are heavily infested with the green peach aphid ⁇ Myzus persicae) are treated by being dipped into the preparation of active compound of the desired concentration.
  • the kill is determined in%. 100% means that all aphids have been killed; 0% means that no aphids have been killed.
  • the determined kill values are calculated according to the Colby formula (see page 1).
  • Emulsifier 2 parts by weight of alkylaryl polyglycol ether
  • active compound 1 part by weight of active compound is mixed with the indicated amounts of solvent and emulsifier, and the concentrate is diluted with emulsifier-containing water to the desired concentration.
  • Cabbage leaves (Brassica oleraceä) are treated by being dipped into the preparation of active compound of the desired concentration and are populated with larvae of the horseradish leaf beetle ⁇ Phaedon cochleariae) while the leaves are still moist.
  • the kill is determined in%. 100% means that all beetle larvae have been killed; 0% means that no beetle larvae have been killed.
  • the determined kill values are calculated according to the Colby formula (see page 1).

Abstract

L'invention concerne de nouvelles combinaisons de principes actifs qui sont constituées de céto-énols cycliques définis de formule (I), dans laquelle A, B, D, G, W, X, Y et Z ont les significations mentionnées dans la description, et/ou de dérivés de l'acide tétronique de formule (II), dans laquelle A', B', G', X', Y', Z' et n' ont les significations mentionnées dans la description, et de phtalamides de formule (III), dans laquelle Hal représente chlore, brome ou iode et * représente un atome de carbone en configuration R ou S, de préférence en configuration S. Ces combinaisons de principes actifs présentent d'excellentes propriétés insecticides et acaricides.
PCT/EP2007/001465 2006-03-06 2007-02-21 Combinaisons de principes actifs à propriétés insecticides et acaricides WO2007101546A2 (fr)

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WO2009118026A1 (fr) * 2008-03-27 2009-10-01 Bayer Cropscience Ag Utilisation de dérivés d'acide tétronique pour lutter contre les insectes et les tétranyques par arrosage, application au goutte-à-goutte ou immersion
WO2019224143A1 (fr) * 2018-05-24 2019-11-28 Bayer Aktiengesellschaft Combinaisons de substances actives à propriétés insecticides, nématicides et acaricides

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AR059884A1 (es) 2008-05-07

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