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WO2006008107A1 - Insecticides et/ou acaricides selectifs a base de composes dicarbonyle substitues cycliques et de phytoprotecteurs - Google Patents

Insecticides et/ou acaricides selectifs a base de composes dicarbonyle substitues cycliques et de phytoprotecteurs Download PDF

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Publication number
WO2006008107A1
WO2006008107A1 PCT/EP2005/007790 EP2005007790W WO2006008107A1 WO 2006008107 A1 WO2006008107 A1 WO 2006008107A1 EP 2005007790 W EP2005007790 W EP 2005007790W WO 2006008107 A1 WO2006008107 A1 WO 2006008107A1
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WIPO (PCT)
Prior art keywords
alkyl
substituted
optionally
hydrogen
alkoxy
Prior art date
Application number
PCT/EP2005/007790
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German (de)
English (en)
Inventor
Reiner Fischer
Udo Reckmann
Chris Rosinger
Erich Sanwald
Christian Arnold
Original Assignee
Bayer Cropscience Ag
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Bayer Cropscience Ag filed Critical Bayer Cropscience Ag
Priority to EA200700316A priority Critical patent/EA200700316A1/xx
Priority to BRPI0513502-8A priority patent/BRPI0513502A/pt
Priority to US11/632,501 priority patent/US20080200499A1/en
Priority to JP2007521873A priority patent/JP2008506739A/ja
Priority to MX2007000636A priority patent/MX2007000636A/es
Priority to CA002574199A priority patent/CA2574199A1/fr
Priority to AU2005263566A priority patent/AU2005263566A1/en
Priority to EP05762457A priority patent/EP1773126A1/fr
Publication of WO2006008107A1 publication Critical patent/WO2006008107A1/fr

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Classifications

    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
    • A01N25/32—Ingredients for reducing the noxious effect of the active substances to organisms other than pests, e.g. toxicity reducing compositions, self-destructing compositions
    • 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
    • A01N33/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds
    • A01N33/16—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds containing nitrogen-to-oxygen bonds
    • A01N33/18—Nitro compounds
    • A01N33/20—Nitro compounds containing oxygen or sulfur attached to the carbon skeleton containing the nitro group
    • A01N33/22—Nitro compounds containing oxygen or sulfur attached to the carbon skeleton containing the nitro group having at least one oxygen or sulfur atom and at least one nitro group directly attached to the same aromatic ring system
    • 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
    • A01N33/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds
    • 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
    • A01N33/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds
    • A01N33/16—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds containing nitrogen-to-oxygen bonds
    • 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
    • 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 invention relates to the use of selective insecticidal and / or acaricidal combinations of active substances which contain substituted cyclic dicarbonyl compounds on the one hand and at least one crop plant compatibility-improving compound on the other hand for selective insect and / or spider mite control in various crops.
  • the invention relates to the use of selective insecticidal and / or acaricidal agents ent ⁇ holding an effective content of a drug combination comprising as components
  • W and Z independently of one another represent hydrogen, halogen, alkyl, alkenyl, alkynyl, alkoxy, alkenyloxy, haloalkyl, haloalkoxy, haloalkenyloxy, nitro or cyano,
  • X represents halogen, alkyl, alkenyl, alkynyl, alkoxy, alkenyloxy, alkylthio, alkylsulfinyl, alkylsulfonyl, haloalkyl, haloalkoxy, haloalkenyloxy, nitro or cyano,
  • Y is hydrogen, halogen, alkyl, haloalkyl, haloalkoxy, nitro, cyano or unsubstituted or substituted phenyl or hetaryl,
  • B is hydrogen, alkyl or alkoxyalkyl, or
  • 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, alkenyl, alkynyl, alkoxyalkyl, saturated or unsaturated cycloalkyl in which optionally one or more ring members are replaced by heteroatoms, arylalkyl, aryl, hetarylalkyl or hetaryl or
  • 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, or
  • a and Cy together represent alkanediyl or alkenediyl optionally substituted by hydroxy, in each case optionally substituted alkyl, alkoxy, alkylthio, cycloalkyl, benzyloxy or aryl, or
  • Q 1 is hydrogen or alkyl
  • Q ⁇ 5 Q ⁇ J Q ⁇ and Q ⁇ independently of one another represent hydrogen or alkyl
  • Q ⁇ is hydrogen, alkyl, alkoxyalkyl, alkylthioalkyl, optionally substituted
  • Cycloalkyl in which a methylene group is optionally replaced by oxygen or sulfur
  • phenyl optionally substituted phenyl
  • G is halogen or nitro
  • a 1 represents one of the divalent heterocyclic groupings outlined below,
  • n is a number 0, 1, 2, 3, 4 or 5
  • a 2 is optionally substituted by QQ-alkyl and / or C r C 4 -alkoxy-carbonyl and / or C1-C4 alkenyloxy-carbonyl-substituted alkanediyl having 1 or 2 carbon atoms,
  • R 8 is hydroxy, mercapto, amino, C] -C6 alkoxy, Ci-C ⁇ alkylthio, Ci-C 6 -alkylamino or di- (C r C 4 -alkyl) -amino,
  • R 9 is hydroxy, mercapto, amino, Ci-Cv-alkoxy, C j -Cö-alkenyloxy, Ci-Cg-alkenyloxy CPCG-alkoxy, C r C 6 alkylthio, Ci-C 6 -alkylamino or di- (C C 4 alkyl) amino,
  • R 10 is in each case optionally substituted by fluorine, chlorine and / or bromine-substituted C 1 -C 4 -alkyl,
  • R 11 is hydrogen, in each case optionally substituted by fluorine, chlorine and / or bromine substituted Cp C 6 alkyl, C 2 -C 6 alkenyl or C 2 -C 6 alkynyl, C l -C 4 alkoxy-Ci-C 4 alkyl, dioxolanyl-C, -C 4 -alkyl, furyl, furyl-C 1 -C 4 -alkyl, thienyl, thiazolyl, piperidinyl, or optionally substituted by fluorine, chlorine and / or bromine or C r C 4 alkyl substituted phenyl .
  • R 12 is hydrogen, in each case optionally substituted by fluorine, chlorine and / or bromine substituted C r C 6 alkyl, C 2 -C 6 alkenyl or C 2 -C 6 alkynyl, Ci-C 4 alkoxy C r C 4 alkyl, dioxolanylC r C 4 alkyl, furyl, furyl C r C 4 alkyl, thienyl, thiazolyl, piperidinyl, or optionally substituted by fluorine, chlorine and / or bromine or C r C 4 alkyl substituted phenyl, or R 11 and R 12 also together for each optionally optionally Phenyl, furyl, an annulated benzene ring, or substituted C 3 -C 6 alkanediyl or C 2 -C 5 by two substituents which together with the C atom to which they are attached form a 5- or 6-membered carboxycycle Oxaalkanediyl stands,
  • R 13 represents hydrogen, cyano, halogen or represents in each case optionally fluorine, chlorine and / or bromine-substituted C 1 -C 4 -alkyl, C 3 -C 6 -cycloalkyl or phenyl
  • R 14 represents hydrogen, optionally hydroxyl-, cyano-, halogen or Ci-C 4 alkoxy sub ⁇ stitutechnischs C r C 6 alkyl, C 3 -C 6 -cycloalkyl or tri- (C r C alkyl 4> silyl
  • R 15 represents hydrogen, cyano, halogen, or optionally substituted by fluorine, chlorine and / or bromine-substituted C r C 4 alkyl, C 3 -C 6 cycloalkyl or phenyl,
  • X 1 represents nitro, cyano, halogen, C r C 4 alkyl, C, -C 4 haloalkyl, C r C 4 alkoxy or C 1 -C 4 - haloalkoxy,
  • X 2 represents hydrogen, cyano, nitro, halogen, C r C 4 alkyl, C r C 4 haloalkyl, C r C 4 -alkoxy or C r C 4 haloalkoxy,
  • X 3 represents hydrogen, cyano, nitro, halogen, C r C 4 alkyl, C r C 4 haloalkyl, C r C 4 alkoxy or Ci-C is 4 haloalkoxy,
  • R 16 is hydrogen or C 1 -C 4 -alkyl
  • R 17 is hydrogen or C 4 -alkyl r C
  • R 18 represents hydrogen, in each case optionally cyano-, halogen or C r C 4 alkoxy substitu ⁇ jewes Ci-C 6 alkyl, C r C 6 alkoxy, C r C 6 alkylthio, C r C 6 alkylamino or di - (C r C 4 alkyl) - amino, or in each case optionally cyano-, halogen or Ci-C 4 -alkyl-substituted C 3 -C 6 cycloalkyl, C 3 -C 6 cycloalkyloxy, C 3 -C 6 cycloalkylthio or C 3 -C 6 -cycloalkylamino,
  • R 19 represents hydrogen, optionally cyano-, hydroxyl-, halogen or Ci-C 4 alkoxy substitu ⁇ jewes C r C 6 -alkyl, in each case optionally cyano- or halogen-substituted C 3 -C 6 - alkenyl or C 3 -C 6 - alkynyl, or optionally cyano-, halogen or C r C 4 -alkyl-substituted C 3 -C 6 cycloalkyl,
  • R 20 represents hydrogen, optionally cyano-, hydroxyl-, halogen or C r C 4 alkoxy substitu ⁇ jewes Ci-C 6 -alkyl, in each case optionally substituted by cyano or halogen, C 3 -C 6 - alkenyl or C 3 -C 6 - alkynyl optionally sub ⁇ stitutechnischs cyano-, halogen or C] -C 4 -alkyl C 3 -C 6 cycloalkyl, or optionally substituted by nitro, cyano, halogen, C r C 4 alkyl, C r C 4 haloalkyl, C r C 4 alkoxy or Ci-C is 4 -haloalkoxy-substituted phenyl, or substituted for 19 in each case optionally C r C 4 alkyl C 2 -C 6 together with R - alkanediyl or C 2 -C 5 -oxaalkanediyl
  • X is nitro, cyano, carboxy, carbamoyl, formyl, sulfamoyl, hydroxy, amino, halo, Cp C4 alkyl, C] -C 4 haloalkyl, C] -C 4 alkoxy or Ci-C is 4 haloalkoxy, and
  • X 5 represents nitro, cyano, carboxy, carbamoyl, formyl, sulfamoyl, hydroxy, amino, halo, C] - C4 alkyl, Ci-C4-haloalkyl, Ci-C 4 -alkoxy or C r C 4 haloalkoxy
  • hydrocarbon chains as in alkyl or alkanediyl - also in Ver ⁇ bond with heteroatoms, such as in alkoxy - are straight-chain or branched.
  • the compounds of the formula (I) can be present in different compositions as geometric and / or optical isomers or mixtures of isomers, which can optionally be separated in a customary manner. Both the pure isomers and the isomer mixtures, as well as their use and agents containing them are the subject of the present invention. However, in the following, for the sake of simplicity, compounds of the formula (I) will always be mentioned, although both the pure compounds are meant, if appropriate, also mixtures with different proportions of isomeric compounds.
  • A, B, D, G, Q 1 , Q 2 , Q 3 , Q 4 , Q 5 , Q 6 , W, X, Y and Z are as defined above.
  • substituted cyclic dicarbonyl compounds of the insecticidal and / or acaricidal agents are generally defined by the formula (I). Preferred substituents or ranges of the radicals listed in the formulas mentioned above and below are explained below:
  • W and Z independently of one another preferably represent hydrogen, halogen, C 1 -C 5 -alkyl, C 1 -C 6 -halogenoalkyl or C 1 -C 8 -alkoxy,
  • X is preferably halogen, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 1 -C 6 -haloalkyl, C 1 -C -alkoxy, C 3 -C 6 -alkenyloxy, Cj-Cg-haloalkoxy, C3-C6-haloalkenyl-oxy, nitro or cyano, preferably represents hydrogen, halogen, Ci-C 4 alkyl, C r C 2 -haloalkyl, C r C 2 - haloalkoxy, cyano or one of the radicals
  • V ! is hydrogen, halogen, C j -C 12 "Alky 1, C j -CG-alkoxy, C ⁇ -C 4 haloalkyl, C j -C 4 logenalkoxy -Ha-, nitro or cyano,
  • V ⁇ and V * are independently hydrogen, halogen, C j -CG alkyl, C j -CG-alkoxy, CJ-C4-haloalkyl or Cj-C ⁇ haloalkoxy,
  • CDC preferably stands for one of the groups
  • A preferably represents hydrogen or respectively optionally halogen-substituted C 1 -C 2 -alkyl, C 3 -C 8 alkenyl, C ⁇ C 1 -alkoxy-C 1 Q -CG alkyl, C 1 -C 1 O-AHCyItInO C 1 -C 6 -alkyl, optionally substituted by halogen, C 1 -Cg-AIlCyI or C 1 -Cg-AIkOXy substituted C 3 - Cg-cycloalkyl, in which optionally one or two non-directly adjacent ring members by oxygen and / or sulfur or, if appropriate, phenyl or phenyl-C 1 -C 6 -halogen substituted by halogen, C 1 -C -alkenyl, C 1 -C 6 -halogenoalkyl, C 1 -CG -alkoxy, C 1 -CG -halogenoalkoxy, cyano or nitro. alky
  • B preferably represents hydrogen, C 1 -C 1 2 alkyl or C 1 -C g-alkoxy-C1 -CG alkyl, or
  • A, B and the carbon atom to which they are attached preferably represent saturated C 3 - C ⁇ cycloalkyl or unsaturated C5-C 1 o-cycloalkyl in which optionally one
  • Ring member is replaced by oxygen or sulfur and which optionally mono- or disubstituted by C 1 -Cg -AllCyI, C 3 -C 1 O-CyClOaIlCyI, C ⁇ Cg-haloalkyl, C 1 -Cg-
  • A, B and the carbon atom to which they are attached are preferably C5-C6-cycloalkyl which is not directly adjacent to any one or two
  • A, B and the carbon atom to which they are attached are preferably C 3 -C 6 -cycloalkyl or C 5 -C 8 -cycloalkenyl in which two substituents together with the carbon atoms to which they are attached are each optionally substituted by C 1 -Cg-alkyl, C 1 -Cg -alkoxy or halogen-substituted C 2 -C 6 -alkanediyl, C 2 -C 6 -alkendiyl or C 4 -C 5 -alkanediyl, in which optionally a methylene group is replaced by oxygen or sulfur,
  • D preferably represents hydrogen, in each case optionally halogen-substituted C 1 -C 12 -alkyl, C 3 -CG-alkenyl, C 3 -CG-alkynyl, C 1 -C 12 -alkoxy, -Cg-alkyl, where appropriate by halogen, substituted C 3 -C 9 -cycloalkyl in which optionally one ring member is replaced by oxygen or sulfur or in each case optionally substituted by halogen, C 1 -C 8 -alkyl, C 1 -C 6 -halogenoalkyl,
  • a and D together are preferably each optionally substituted C ⁇ -Cg-alkanediyl or C ⁇ -Cg-alkenediyl, wherein optionally a methylene group is replaced by a carbonyl group, oxygen or sulfur, and
  • Halogen hydroxy, mercapto or in each case optionally substituted by halogen
  • a and Q! together preferably represent in each case optionally monosubstituted or disubstituted by identical or different halogen, by in each case optionally mono- to trisubstituted by identical or different halogen-substituted C] -C] 0 alkyl, C] -CG-alkoxy, C j -Cg-
  • Oxygen atom is bridged or
  • Q 1 is preferably hydrogen or C 1 -C 4 -alkyl
  • Q ⁇ J ⁇ Q> Q ⁇ Q ⁇ un d are each independently preferably represents hydrogen or Cj-C4 alkyl
  • Q 3 preferably represents hydrogen, Cj-Cg alkyl, Cj-Cg-alkoxy-Ci ⁇ alkyl, C j -Cg- alkylthio Cj-C2-alkyl, optionally substituted by halogen, Cj-C ⁇ alkyl or C] - C4-alkoxy-substituted C3-C8-cycloalkyl in which optionally one methylene group is replaced by oxygen or sulfur or optionally halogen-, C j -C ⁇ alkyl, Cj-C4 alkoxy, Cj-C2 haloalkyl, C] -C2 Haloalkoxy, cyano or nitro substituted phenyl or
  • Q 3 and Q 1 together with the carbon atom to which they are attached are preferably an optionally C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy or C 1 -C 2 -haloalkyl substituted C 3 -Cy ring in which optionally a ring member is replaced by oxygen or sulfur,
  • G is preferably chlorine, bromine or nitro.
  • halogen is fluorine, chlorine, bromine and iodine, in particular fluorine, chlorine and bromine.
  • W and Z independently of one another particularly preferably represent hydrogen, chlorine, bromine, C ⁇ - C 3 alkyl or C 1 -C 3 -alkoxy,
  • X particularly preferably represents chlorine, bromine, Cj-C ⁇ alkyl, Cj-C4 alkoxy, Cj-C 3 - halogenoalkyl, C j -C 3 haloalkoxy or cyano,
  • Y is particularly preferably hydrogen, chlorine, bromine, C 1 -C 2 -alkyl, trifluoromethyl or the radical
  • Vi particularly preferably represents hydrogen, fluorine, chlorine, bromine, Ci-Cg-alkyl, C1-C4 alkoxy, Cj-C2 haloalkyl, C] -C2 -haloalkoxy, nitro or cyano,
  • V 1 particularly preferably represents hydrogen, fluorine, chlorine, bromine, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 2 -haloalkyl or C 1 -C 2 -haloalkoxy,
  • CDC is particularly preferred for one of the groups
  • B is particularly preferably hydrogen or C 1 -C 6 -alkyl, or
  • A, B and the carbon atom to which they are attached are particularly preferably saturated C 3 -C 7 -cycloalkyl, wherein optionally a ring member is represented by oxygen or
  • A, B and the carbon atom to which they are attached are particularly preferably C5-C6-cycloalkyl which is substituted by an optionally one or two oxygen or sulfur atoms not directly adjacent or optionally substituted by methyl or ethyl alkylenediyl or by an alkylenedioxy Is substituted with the carbon atom to which it is attached forms another five- or six-membered ring, with the proviso that Q 3 is then particularly preferably hydrogen or methyl, or
  • A, B and the carbon atom to which they are attached are more preferably C3-C6 cycloalkyl or C5-C6 cycloalkenyl in which two substituents together with the carbon atoms to which they are attached are each optionally substituted by methyl or methoxy-substituted C 2 -C 4 -alkanediyl, C 2 -C 4 -alkendiyl, where appropriate where a methylene group is replaced by oxygen, or butadienediyl, with the proviso that Q 3 is then particularly preferably hydrogen or methyl,
  • D particularly preferably represents hydrogen, in each case optionally mono- to trisubstituted by fluorine or chlorine, C 1 -C 6 -alkyl, C 3 -C 9 -alkenyl, C 1 -C 4 -alkoxy-C 2 -C 3 -alkyl, where appropriate simply by C 1 -C 2 -alkyl- Alkyl, C 1 -C 2 -alkoxy or trifluoromethyl-substituted C 3 -C 7 -cycloalkyl in which optionally a methylene group is replaced by oxygen or sulfur or (but not in the case of Compounds of the formulas (1-1)) for each optionally mono- to disubstituted by fluorine, chlorine, bromine, C j -C ⁇ alkyl, C j ⁇ -haloalkyl, Ci-C ⁇ alkoxy or C 1 -C 2 halo genalkoxy substituted phenyl , Pyridyl or benz
  • a and D are together particularly preferably substituted or unsubstituted C3-C5 alkanediyl in which a methylene group may be replaced by oxygen or sulfur, wherein as substituents Cj-C2-alkyl is suitable, or
  • a and D are (in the case of the compounds of the formula (I-1)) together with the atoms to which they are attached, for one of the groups AD-I to AD-10:
  • AD-10 A and Q! together particularly preferably represent in each case optionally mono- or disubstituted by identical or different Ci-C2-alkyl or C j -C 2 -alkoxy-substituted C3-C4-alkanediyl or C3-C4-alkenediyl or
  • Q * is particularly preferably hydrogen
  • Q ⁇ is particularly preferably hydrogen
  • Q4, Q5 and Q4 particularly preferably independently of one another represent hydrogen or Cj-C2-alkyl
  • Q particularly preferably represents hydrogen, C ⁇ -C ⁇ alkyl, Ci-C4-alkoxy-Ci-C2-alkyl, C j - C4-alkylthio-Ci-C2-alkyl or optionally methyl- or methoxy-substituted C3-C6 -Cycloalkyl, wherein optionally a methylene group by oxygen or
  • Q ⁇ and Q ⁇ are particularly preferably a together with the carbon to which they are bonded, represent an optionally mono- or disubstituted by Ci-C4-alkyl or C j -C 4 -alkoxy-substituted saturated C5-Cg ring, in which optionally Ring member is replaced by oxygen or sulfur,
  • A is then more preferably hydrogen or methyl
  • G is particularly preferably chlorine or nitro.
  • halogen is fluorine, chlorine, bromine and iodine, in particular fluorine, chlorine and bromine.
  • W and Z independently of one another very particularly preferably represent hydrogen, chlorine, bromine, methyl, ethyl, methoxy or ethoxy,
  • X very particularly preferably represents chlorine, bromine, methyl, ethyl, propyl, methoxy, ethoxy,
  • Y very particularly preferably represents hydrogen, chlorine, bromine, methyl, trifluoromethyl or the radical
  • V 1 very particularly preferably represents hydrogen, fluorine, chlorine, bromine, methyl, ethyl, tert-butyl, methoxy, trifluoromethyl or trifluoromethoxy,
  • V 1 very particularly preferably represents hydrogen, fluorine, chlorine, methyl, methoxy or trifluoromethyl
  • CDC is most preferably one of the groups
  • B is very particularly preferably hydrogen, methyl or ethyl, or
  • A, B and the carbon atom to which they are attached very particularly preferably represent saturated C 5 -C 9 -cycloalkyl in which optionally a ring member is replaced by oxygen and which may be readily substituted by methyl, trifluoromethyl, methoxy, ethoxy, propoxy, butoxy or Isobutoxy is substituted, with the proviso that Q 3 is then very particularly preferably hydrogen, or
  • A, B and the carbon atom to which they are attached very particularly preferably represent C 5 -C 5 ( 5-cycloalkyl which is substituted by an alkylenedioxy group containing two oxygen atoms which are not directly adjacent, with the proviso that Q.
  • D very particularly preferably represents hydrogen
  • D very particularly preferably represents hydrogen
  • a and D are together most preferably optionally substituted C3-C5 alkanediyl, wherein optionally one carbon atom is replaced by oxygen or sulfur and which is optionally mono- or di-substituted by methyl, or
  • a and D are (in the case of the compounds of formula (I-1)) together with the atoms to which they are attached, for the group:
  • a and Cr together are very particularly preferably C3-C4-alkanediyl which is optionally monosubstituted or disubstituted by methyl or methoxy
  • Q! is very particularly preferably hydrogen
  • Q 1 very particularly preferably represents hydrogen
  • Q4, Q5 and Q4 very particularly preferably independently of one another represent hydrogen or methyl
  • Q3 very particularly preferably represents hydrogen, methyl, ethyl or C3-C6-cycloalkyl, or
  • Q- * and Q ⁇ are most preferably together with the carbon to which they are attached, for an optionally substituted by methyl or methoxy saturated C5-Cg ring, in which optionally a ring member by oxygen or Sulfur is replaced, with the proviso that A is then most preferably hydrogen,
  • G is most preferably chlorine or nitro
  • W is particularly preferably hydrogen, chlorine, bromine, methyl, ethyl, methoxy or ethoxy,
  • X is particularly preferably chlorine, bromine, methyl, ethyl, propyl, methoxy, ethoxy, trifluoromethyl, difluoromethoxy, trifluoromethoxy or cyano,
  • Y is particularly preferably hydrogen, chlorine, bromine, methyl, trifluoromethyl or the radical
  • vi is particularly preferably hydrogen, fluorine, chlorine, bromine, methyl, ethyl, tert-butyl, methoxy, trifluoromethyl or trifluoromethoxy,
  • V 1 is particularly preferably hydrogen, fluorine, chlorine, methyl, methoxy or trifluoromethyl,
  • Z is particularly preferably hydrogen, methyl, chlorine or bromine
  • CDC is particularly preferred for one of the groups
  • B is particularly preferably hydrogen, methyl or ethyl, or A, B and the carbon atom to which they are attached are particularly preferably saturated C 5 -C 9 -cycloalkyl in which optionally one ring member is replaced by oxygen and which is optionally monosubstituted by methyl, trifluoromethyl, methoxy, ethoxy, propoxy, butoxy or isobutoxy is substituted,
  • D is particularly preferably hydrogen
  • G is especially preferred for chlorine.
  • Particularly preferred according to the invention is the use of the compounds of the formula (I) which contain a combination of the meanings listed above as being particularly preferred.
  • Particularly preferred according to the invention is the use of the compounds of the formula (I) which contain a combination of the meanings listed above as being particularly preferred.
  • Saturated or unsaturated hydrocarbon radicals such as alkyl, alkylenediyl or alkenyl may also be used in conjunction with heteroatoms, e.g. in alkoxy, as far as possible, in each case straight-chain or branched.
  • optionally substituted radicals may be monosubstituted or polysubstituted, with multiple substituents the substituents being the same or different.
  • W C 2 H 5 ;
  • X CH 3 ;
  • Y 4-Cl;
  • Z H;
  • W C 2 H 5 ;
  • X CH 3 ;
  • Y 4-Br;
  • Z H;
  • W C 2 H 5 ;
  • X C 2 H 5 ;
  • Y 4-Cl;
  • Z H;
  • W C 2 H 5 ;
  • X C 2 H 5 ;
  • Y 4-Br;
  • Z H;
  • W C 2 H 5 ;
  • X Br;
  • Y 4-Br;
  • Z H;
  • W C 2 H 5 ;
  • X Br;
  • Y 4-Cl;
  • Z H;
  • Table 20 A, B and D as indicated in Table 1
  • W C 2 H 5 ;
  • X Cl;
  • Y 4-CH 3 ;
  • Z H;
  • W C 2 H 5 ;
  • X Br;
  • Y 4-CH 3 ;
  • Z H;
  • W C 2 H 5 ;
  • X CH 3 ;
  • Y 4-CH 3 ;
  • Z H;
  • W C 2 H 5 ;
  • X C 2 H 5 ;
  • Y 4-CH 3 ;
  • Z H;
  • m is preferably 0, 1, 2, 3 or 4.
  • a 1 preferably represents one of the divalent heterocyclic groupings outlined below
  • n preferably represents the numbers 0, 1, 2, 3 or 4.
  • a 2 preferably represents in each case optionally methyl, ethyl, methoxycarbonyl or ethoxycarbonyl or allyloxycarbonyl-substituted methylene or ethylene.
  • R 8 is preferably hydroxy, mercapto, amino, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methylthio, ethylthio, n- or i-propylthio, n-, i -, s- or t-butylthio, methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino, dimethylamino or diethylamino.
  • R 9 is preferably hydroxy, mercapto, amino, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, 1-methylhexyloxy, allyloxy, 1-allyloxymethyl-ethoxy, methylthio, ethyl ⁇ thio, n- or i-propylthio, n-, i-, s- or t-butylthio, methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino, dimethylamino or diethylamino ,
  • R 10 preferably represents in each case optionally fluorine, chlorine and / or bromine-substituted methyl, ethyl, n- or i-propyl.
  • R 11 is preferably hydrogen, in each case optionally substituted by fluorine and / or chlorine-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, propenyl, butenyl, propynyl or butynyl, Methoxymethyl, ethoxymethyl, methoxyethyl, ethoxyethyl, dioxolanylmethyl, furyl, furylmethyl, thienyl, thiazolyl, piperidinyl, or optionally by fluorine, chlorine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl substituted phenyl.
  • R 12 is preferably hydrogen, in each case optionally substituted by fluorine and / or chlorine-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, propenyl, butenyl, propynyl or butynyl, Methoxymethyl, ethoxymethyl, methoxyethyl, ethoxyethyl, dioxolanylmethyl, furyl, furylmethyl, thienyl, thiazolyl, piperidinyl, or optionally by fluorine, chlorine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl substituted phenyl, or together with R 1 1 represents one of the radicals -CH 2 -O-CH 2 -CH 2 - and -CH 2 -CH 2 -O-CH 2 -CH 2
  • R 13 is preferably hydrogen, cyano, fluorine, chlorine, bromine, or in each case optionally substituted by fluorine, chlorine and / or bromine substituted methyl, ethyl, n- or i-propyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl or phenyl ,
  • R 14 is preferably hydrogen, optionally methyl, ethyl, n- or i-propyl, n-, i-, s- or t-substituted by hydroxyl, cyano, fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy. butyl.
  • R 15 preferably represents hydrogen, cyano, fluorine, chlorine, bromine, or represents in each case optionally fluorine, chlorine and / or bromine-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t- Butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl or phenyl.
  • X 1 is preferably nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, difluoromethyl, dichloromethyl, trifluoromethyl, trichloromethyl, chlorodifluoromethyl , Fluorodichloromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy or trifluoromethoxy.
  • X 2 is preferably hydrogen, nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, difluoromethyl, dichloromethyl, trifluoromethyl, trichloromethyl, chlorodifluoromethyl , Fluorodichloromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy or trifluoromethoxy.
  • X 3 is preferably hydrogen, nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, difluoromethyl, dichloromethyl, trifluoromethyl, trichloromethyl, chlorodifluoromethyl , Fluorodichloromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy or trifluoromethoxy.
  • t preferably stands for the numbers 0, 1, 2, 3 or 4.
  • v preferably represents the numbers 0, 1, 2, 3 or 4.
  • R 16 is preferably hydrogen, methyl, ethyl, n- or i-propyl.
  • R 17 is preferably hydrogen, methyl, ethyl, n- or i-propyl.
  • R 18 preferably represents hydrogen, in each case optionally cyano, fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl , Methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, Methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino, dimethylamino or diethylamino, or in each case optionally by cyano, fluorine, chlorine, bromine, methyl
  • R 19 is preferably hydrogen, in each case optionally cyano, hydroxyl, fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy-substituted methyl, ethyl, n- or i-propyl, n-, i- or s-butyl, each optionally substituted by cyano, fluorine, chlorine or bromine substituted propenyl, Butenyl, propynyl or butynyl, or in each case optionally substituted by cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl-substituted cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl.
  • R? O preferably represents hydrogen, in each case optionally cyano-, hydroxyl-, fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy-substituted methyl, ethyl, n- or i-propyl, n-, i- or s-butyl , in each case optionally substituted by cyano, fluorine, chlorine or bromine substituted propenyl,
  • Cyclohexyl or optionally by nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl, methoxy, ethoxy, n- or i- Propoxy, di-fluoromethoxy or trifluoromethoxy-substituted phenyl, or together with R 19 for each optionally substituted by methyl or ethyl butane-1,4-diyl (trimethylene), pentane
  • X 4 is preferably nitro, cyano, carboxy, carbamoyl, formyl, sulfamoyl, hydroxy, amino, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl , Trifluoromethyl,
  • X 5 is preferably nitro, cyano, carboxy, carbamoyl, formyl, sulfamoyl, hydroxy, amino, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl , Trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy or trifluoromethoxy.
  • herbicidal safeners very particular preferred compounds of the formula (Ha) are listed in the table below.
  • herbicidal safeners particularly preferred compounds of the formula (Hb) according to the invention are listed in the table below.
  • herbicidal safeners according to the invention very particularly preferred compounds of formula (He) are listed in the table below.
  • herbicidal safeners according to the invention very particularly preferred compounds of formula (Hd) are listed in the table below.
  • herbicidal safeners according to the invention very particularly preferred compounds of formula (De) are listed in the table below.
  • crop plant compatibility-improving compound [component (b)] are cloquintocet-mexyl, fenchlorazole-ethyl, isoxadifen-ethyl, mefenpyr-diethyl, furilazole, fenclorim, cumyluron, dymron, dichloromide, dimepiperate and the compounds IIe-5 and He 11 most preferred, with cloquintocet-mexyl, mefenpyr-diethyl, isoxadifen-ethyl, furilazoles, dichloromide, fenclorim and IIe-5 being particularly emphasized.
  • Examples of the selective herbicidal combinations according to the invention of in each case one active compound of the formula (I) and in each case one of the safeners defined above are listed in the table below.
  • the compounds of general formula (Ha) to be used as safeners are known and / or can be prepared by processes known per se (cf., WO-A-91/07874, WO-A-95/07897).
  • the compounds of general formula (He) to be used as safeners are known and / or can be prepared by processes known per se (cf., DE-A-2218097, DE-A-2350547).
  • the compounds of the general formula (Ee) to be used as safeners are known and / or can be prepared by processes known per se (cf., WO-A-99/66795 / US-A-6251827).
  • the active ingredient combinations may be e.g. used in the following plants:
  • the beneficial effect of the active ingredient combinations is particularly pronounced in certain concentration ratios.
  • the weight ratios of the active ingredients in the active substance combinations can be varied in relatively large ranges.
  • 1 part by weight of active compound of the formula (T) or its salts accounts for 0.001 to 1000 parts by weight, preferably 0.01 to 100 parts by weight, more preferably 0.05 to 10 parts by weight and most preferably 0.07 to 1.5 parts by weight of one of above under (b), the crop plants compatibility ver ⁇ improving compounds (antidotes / safeners).
  • the active compounds or active compound combinations can be converted into the customary formulations, such as solutions, emulsions, wettable powders, suspensions, powders, dusts, pastes, soluble powders, granules, suspension-emulsion concentrates, active ingredient-impregnated natural and synthetic thetic Substances and fine encapsulation in polymeric substances.
  • formulations are prepared in a known manner, for. Example, by mixing the active compounds with extenders, that is liquid solvents and / or solid carriers, optionally with the use of surfactants, emulsifiers and / or dispersants and / or foam-forming agents.
  • 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 carbon hydrogens, such as cyclohexane or paraffins, for example petroleum fractions, mineral and vegetable oils, alcohols, such as butanol or glycol and their ethers and esters, ketones, such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents, such as dimethylformamide and dimethyl sulfoxide, as well as water.
  • aliphatic carbon hydrogens such as cyclohexane or paraffins, for example petroleum fractions, mineral and vegetable oils
  • alcohols such as butanol or glycol and their ethers and esters
  • ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone
  • strongly polar solvents such as dimethylformamide and dimethyl sul
  • 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 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, alkylsulfates, arylsulfonates and protein hydrolysates; suitable dispersants are: e.g. Lignin-sulphite liquors and methylcellulose.
  • adhesives such as carboxymethyl cellulose, natural and synthetic synthetic powdery, granular or latex-like polymers, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, and natural phospholipids, such as cephalins and lecithins and synthetic phospholipids.
  • Other additives may 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.
  • 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.
  • the formulations generally contain between 0.1 and 95% by weight of active ingredients including safener agents, preferably between 0.5 and 90%.
  • the active ingredient combinations are generally applied in the form of ready-to-use formulations.
  • the active substances contained in the active ingredient combinations can also be mixed in individual formulations in the application, i. in the form of tank mixes.
  • the active ingredient combinations can continue to be used as such or in their formulations in admixture with other known herbicides, which in turn Fertig ⁇ formulations or tank mixes are possible. Also a mixture with other known active ingredients, such as fungicides, insecticides, acaricides, nematocides, attractants, sterilants, Bactericides, protective agents, bird repellants, growth substances, plant nutrients and soil structure improvers is possible. For certain applications, especially post-emergence, it may also be advantageous to take into the formulations as further additives plant-compatible mineral or vegetable oils (eg the commercial preparation "Rako Binol") or ammonium salts such as ammonium sulfate or ammonium thiocyanate.
  • plant-compatible mineral or vegetable oils eg the commercial preparation "Rako Binol”
  • ammonium salts such as ammonium sulfate or ammonium thiocyanate.
  • the active compound combinations can be used as such, in the form of their formulations or the use forms prepared therefrom by further dilution, such as ready-to-use solutions, suspensions, emulsions, powders, pastes and granules.
  • the application is done in the usual way, e.g. by pouring, spraying, spraying, dusts or spreading.
  • the application rates of the active compound combinations can be varied within a certain range; they hang u.a. weather and soil factors. In general, the application rates are between 0.005 and 5 kg per ha, preferably between 0.01 and 2 kg per ha, more preferably between 0.05 and 1.0 kg per ha.
  • the active ingredient combinations can be applied before and after emergence of the plants, ie in the pre-emergence and postemergence process.
  • the safeners to be used can be used for pretreatment of the seed of the crop (seed dressing) or introduced into the seed furrows before sowing or applied together with the herbicide before or after the plants have run off.
  • the active ingredient combinations are suitable for controlling animal pests, preferably arthropods and nematodes, in particular insects and arachnids, which occur in agriculture, animal health in forests, in the protection of stored products and materials, and in the hygiene sector. They are effective against normally sensitive and resistant species as well as against all or individual stages of development.
  • animal pests preferably arthropods and nematodes, in particular insects and arachnids, which occur in agriculture, animal health in forests, in the protection of stored products and materials, and in the hygiene sector. They are effective against normally sensitive and resistant species as well as against all or individual stages of development.
  • the above mentioned pests include:
  • Symphyla e.g. Scutigerella immaculata.
  • Thysanura eg Lepisma saccharina.
  • Collembola eg Onychiurus armatus.
  • Orthoptera e.g. Acheta domesticus, Gryllotalpa spp., Locusta migratoria migratorioides, Melanoplus spp., Schistocerca gregaria.
  • Phthiraptera e.g. Pediculus humanus corporis, Haematopinus spp., Linognathus spp., Trichodectes spp., Damalinia spp.
  • Thysanoptera e.g. Herculothrips femoralis, Thrips tabaci, Thrips palmi, Frankliniella occidentalis.
  • Heteroptera e.g. Eurygaster spp., Dysdercus intermedius, Piesma quadrata, Cimex lectularius, Rhodnius prolixus, Triatoma spp.
  • Lepidoptera e.g. Pectinophora gossypiella, Bupalus piniarius, Cheimatobia brumata, Lithocolletis blancardella, Hyponomeuta padella, Plutella xylostella, Malacosoma neustria, Euproctis chrysorrhoea, Lymantria spp., Bucculatrix thurberiella, Phyllocnistis citrella, Agrotis spp., Euxoa spp., Feltia spp., Earias insulana, Heliothis Spp., Mamestra brassicae, Panolis flammea, Spodoptera spp., Trichoplusia ni, Carpocapsa pomonella, Pieris spp., Chilo spp., Pyrausta nubilalis, Ephestia kuehniella, Galleria me
  • Hymenoptera e.g. Diprion spp., Hoplocampa spp., Lasius spp., Monomorium pharaonis, Vespa spp.
  • Diptera e.g. Aedes spp., Anopheles spp., Culex spp., Drosophila melanogaster, Musca spp., Fannia spp., Calliphora erythrocephala, Lucilia spp., Chrysomyia spp., Cuterebra spp., Gastrophilus spp., Hyppobosca spp., Stomoxys spp.
  • Oestrus spp. Hypoderma spp., Tabanus spp., Tannia spp., Bibio hortulanus, Oscinella frit, Phorbia spp., Pegomyia hyoscyami, Ceratitis capitata, Dacus oleae, Tipula paludosa, Hylemyia spp., Liriomyza spp.
  • siphonaptera e.g. Xenopsylla cheopis, Ceratophyllus spp.
  • arachnids e.g. Scorpio maurus, Latrodectus mactans, Acarus siro, Argas spp., Ornithodoros spp., Dermanyssus gallinae, Eriophyes ribis, Phyllocoptruta oleivora, Boophilus spp., Rhipicephalus spp., Amblyomma spp., Hyalomma spp., Ixodes spp., Psoroptes spp.
  • Chorioptes spp. Sarcoptes spp., Tarsonemus spp., Bryobia praetiosa, Panonychus spp., Tetranychus spp., Hemitarsonemus spp., Brevipalpus spp.
  • the 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., Bursaphelenchus spp.
  • the active ingredient combinations 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 0.0000001 to 95% by weight of active ingredient, preferably between 0.0001 and 1% by weight.
  • plants and parts of plants can be treated.
  • 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 that 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 ein ⁇ finally protectable by plant variety rights or non-protectable plant varieties.
  • 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, by way of example, leaves, needles, stems, stems, flowers, fruiting bodies, fruits and seeds and roots, tubers and rhizomes .
  • the plant parts also include crops as well as vegetative and generative propagation material, for example cuttings, tubers, rhiomes, offshoots and seeds.
  • the treatment according to the invention of the plants and plant parts with the active ingredients is carried out directly or by acting on their environment, habitat or storage space according to the usual treatment methods, e.g. by dipping, spraying, vaporizing, atomizing, spreading, spreading and in propagation material, in particular in seeds, further by single or multi-layer wrapping.
  • plants and their parts can be treated.
  • wild species 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 if appropriate in combination with conventional methods (Genetically Modified Organisms), and parts thereof are treated.
  • the term “parts” or “parts of plants” or “plant parts” has been explained above.
  • plants of the respective commercially available or in use custom plant cultivars are particularly preferably treated.
  • the treatment according to the invention may also give rise to superadditive ("synergistic") effects.
  • superadditive for example, reduced amounts of expenditure and / or extensions of the spectrum of action and / or an increase in the effect of the substances and agents which can be used according to the invention, better plant growth, increased tolerance to high or low temperatures, increased tolerance to drought or to water or soil salt content, increased flowering power, easier harvesting, acceleration of the crop Ripe, higher crop yields, higher quality and / or higher nutritional value of the harvested products, higher shelf life and / or workability of the harvest products possible, which go beyond the expected effects actually.
  • the preferred plants or plant cultivars to be treated according to the invention which are 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"). Examples of such properties are better plant growth, increased tolerance to high or low temperatures, increased tolerance to dryness or to water or soil salt content, increased flowering efficiency, 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.
  • transgenic plants include the important crop plants, such as cereals (wheat, rice), maize, soya, potato, cotton, oilseed rape and fruit plants (with the fruits apples, pears, citrus fruits and grapes), with corn, soybean Potato, cotton and oilseed rape are particularly emphasized.
  • Traits that are particularly emphasized are the increased defense of the plants against insects by toxins produced in the plants, in particular those which are produced by the genetic material from Bacillus thuringiensis (eg by the genes Cry ⁇ A (a), Cry ⁇ A (b), Cry ⁇ A (c), CryllA, CrylUA, CryIHB2, Cry9c Cry2Ab, Cry3Bb and CryBF and combinations thereof) are produced in the plants (hereinafter "Bt plants”).
  • Bacillus thuringiensis eg by the genes Cry ⁇ A (a), Cry ⁇ A (b), Cry ⁇ A (c), CryllA, CrylUA, CryIHB2, Cry9c Cry2Ab, Cry3Bb and CryBF and combinations thereof
  • Bt plants Traits which are furthermore particularly emphasized are the increased tolerance of the plants to certain herbicidally active compounds, for example imidazolinones, sulfonylureas, glyphosate or phosphin
  • genes which confer the desired properties can also occur in combinations with one another in the transgenic plants.
  • “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 to 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® to Imidazolinone
  • STS® tolerance to sulfonylureas eg corn
  • Clearfield® sold varieties eg maize
  • the listed plants can be treated particularly advantageously according to the invention with the active compound mixtures.
  • the preferred ranges given above for the mixtures also apply to the treatment of these plants.
  • Particularly emphasized is the convinced ⁇ treatment with the mixtures specifically mentioned in the present text.
  • the amount of active ingredient and amount of safener required to produce a 20% WS formulation are dissolved in acetone in an agate mortar and an appropriate amount of the empty formulation (original used to prepare Gaucho 70 WS) is added. It is allowed to dry until even a small residual moisture can be seen. The substance is carefully dissolved with a spatula from the edge of the mortar and mossed until the substance is dry. A corresponding amount of the laboratory formulation thus prepared is weighed into sufficiently large beakers, depending on the amount of seed to be picked, so that these are filled to a maximum of one third with seed during pickling. Add sufficient water (depending on the nature of the seed surface).
  • the seed is then filled into these beakers with formulation and water and pickled on a reagent glass shaker with the aid of a spatula or glass rod. If the formulation is distributed as evenly as possible on the seed, the seed is left to dry under the fume hood.
  • 3 1 plastic trays (20 x 20 x 5 cm) are filled with sandy loam.
  • the earth is pressed with the help of a Andschreibstkovs so that the necessary for the respective culture of deposition depth is achieved.
  • 20 seeds / seed husk are laid out in a uniform manner with the help of tweezers and with the o.g. Stamp pressed.
  • the surface is lightly pressed once again with the Andschreibstempel.
  • an untreated control is also tested. At least 2 bowls are used per variant.
  • the experiment is poured and covered with foil until the plants casserole. After the casserole is watered twice a day. The evaluation is done by counting the accumulated plants and assessing damage (in%) in the period of 5 - 14 days after sowing in comparison to the untreated control.
  • Solvent 7 parts by weight of DMF emulsifier: 2 parts by weight of alkylaryl polyglycol ether
  • active compound 1 part by weight of active compound is mixed with the specified amounts of solvent and emulsifier, and the concentrate is diluted with tap water to the desired concentration.
  • the desired amount of safener in the case of mefenpyr-diethyl as WP 20
  • WP 20 water taken for dilution.
  • 2 g of ai / 1 rapeseed oil methyl ester 500 EW are added.
  • Winter barley leaves in the 2-leaf stage which are attacked by the cereal aphid (Rhopalosiphum padi), are treated with the desired active ingredient and safener concentrations with a bar spray, the amount of water applied being 300 l / ha.
  • at least 2 replicates are used.
  • the evaluation is carried out after 7 d and / or 14 d by assessing the plant damage in%, whereby both the treated plant and the new growth are evaluated and the destruction of the cereal aphids in% compared to the untreated control.
  • 100% damage means that the plant has died and 0% no damage.
  • An effect of 100% on the cereal aphids means that all aphids have been killed; 0% means that no aphids have been killed.
  • the active ingredient is used as SC formulation in the desired concentrations as in variant a) in admixture with mefenpyr-diethyl WP 20 and 2 g of ai / 1 rapeseed oil methyl ester 500 EW.
  • the implementation and evaluation is carried out as indicated in variant a).
  • X means the kill rate when using the active ingredient A at a rate of m g / ha or in a concentration of m ppm
  • Y means the rate of killing when using the active ingredient B in an application rate of n g / ha or in a concentration of n ppm
  • E means the rate at which the active substances A and B are used at rates of application of m and n g / ha or in a concentration of m and n ppm
  • the degree of kill is determined in%. It means 0% a killing degree equal to that of the control, while a killing degree of 100% means that no infestation is observed.
  • the combination is over-additive in its effect, ie there is a synergistic effect.
  • the actually observed kill rate must be greater than the expected kill rate (E) value calculated from the above formula.
  • Adjuvant rapeseed oil methyl ester (0.1% a.i./l)
  • Cotton plants which are heavily infested with the cotton aphid ⁇ Aphis gossypii) are sprayed with the desired concentration of the application solution without dripping.
  • Paprika plants Capsicum sativum
  • Myzus persicae green peach aphid
  • Barley plants (Hordeum vulgare) that are heavily attacked by the cereal aphid (Metopolophium dirhodum) are sprayed to drip point with the desired concentration of the application solution.
  • 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.
  • Test insect Diabrotica balteata - larvae in soil
  • Emulsifier 1 part by weight of alkylaryl polyglycol ether
  • the preparation of active compound is poured onto the ground.
  • the concentration of the active substance in the preparation plays virtually no role, the only decisive factor being the amount of active substance per unit volume of soil, which is stated in ppm (mg / l). Fill the soil in 0.25 1 pots and leave them at 20 0 C.
  • Emulsifier 1 part by weight of alkylaryl polyglycol ether
  • Soybean shoots (Glycine max) of the variety Roundup Ready (trademark of Monsanto Comp. USA) are treated by being dipped into the preparation of active compound of the desired concentration and are populated with the tobacco budworm Heliothis virescens while the leaves are still moist.
  • the kill of the insects is determined.

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Abstract

L'invention concerne l'utilisation d'agents insecticides et/ou acaricides sélectifs caractérisés en ce qu'ils renferment une quantité efficace d'une association de substances actives comprenant : (a) au moins un composé dicarbonyle cyclique substitué de formule (I) dans laquelle W, X, Y et Z sont tels que définis dans la description, et CDC représente un des groupes dicarbonyle mentionnés dans la description, et ; (b) au moins un composé qui améliore la tolérabilité des plantes cultivées, ce composé étant issu du groupe de composés mentionné dans la description, pour lutter contre des insectes et/ou arachnides. La présente invention se rapporte également à un procédé pour lutter contre des insectes et/ou des arachnides au moyen desdits agents.
PCT/EP2005/007790 2004-07-20 2005-07-18 Insecticides et/ou acaricides selectifs a base de composes dicarbonyle substitues cycliques et de phytoprotecteurs WO2006008107A1 (fr)

Priority Applications (8)

Application Number Priority Date Filing Date Title
EA200700316A EA200700316A1 (ru) 2004-07-20 2005-07-18 Селективные инсектициды и акарициды на основе замещённых циклических дикарбонильных соединений и защитных веществ
BRPI0513502-8A BRPI0513502A (pt) 2004-07-20 2005-07-18 inseticidas e/ou acaricidas seletivos à base de compostos dicarbonila cìclicos, substituìdos e protetores
US11/632,501 US20080200499A1 (en) 2004-07-20 2005-07-18 Selective Insecticides and/or Acaricides Based on Substituted Cyclic Dicarbonyl Compounds and Safeners
JP2007521873A JP2008506739A (ja) 2004-07-20 2005-07-18 置換環状ジカルボニル化合物および薬害軽減剤に基づく選択的殺虫剤および／または殺ダニ剤
MX2007000636A MX2007000636A (es) 2004-07-20 2005-07-18 Insecticidas y/o acaricidas selectivos basados en compuestos dicarbonilicos ciclicos sustituidos y agentes detoxificantes.
CA002574199A CA2574199A1 (fr) 2004-07-20 2005-07-18 Insecticides et/ou acaricides selectifs a base de composes dicarbonyle substitues cycliques et de phytoprotecteurs
AU2005263566A AU2005263566A1 (en) 2004-07-20 2005-07-18 Selective insecticides and/or acaricides based on substituted, cyclic dicarbonyl compounds and safeners
EP05762457A EP1773126A1 (fr) 2004-07-20 2005-07-18 Insecticides et/ou acaricides selectifs a base de composes dicarbonyle substitues cycliques et de phytoprotecteurs

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102004035131.7 2004-07-20
DE102004035131A DE102004035131A1 (de) 2004-07-20 2004-07-20 Selektive Insektizide und/oder Akarizide auf Basis von substituierten, cyclischen Dicarbonylverbindungen und Safenern

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WO2006008107A1 true WO2006008107A1 (fr) 2006-01-26

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EP (1) EP1773126A1 (fr)
JP (1) JP2008506739A (fr)
KR (1) KR20070039140A (fr)
CN (2) CN101530101A (fr)
AU (1) AU2005263566A1 (fr)
BR (1) BRPI0513502A (fr)
CA (1) CA2574199A1 (fr)
DE (1) DE102004035131A1 (fr)
EA (1) EA200700316A1 (fr)
MX (1) MX2007000636A (fr)
WO (1) WO2006008107A1 (fr)

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WO2009150093A1 (fr) 2008-06-11 2009-12-17 Syngenta Participations Ag Nouveaux herbicides
US10743535B2 (en) 2017-08-18 2020-08-18 H&K Solutions Llc Insecticide for flight-capable pests

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CN103003276A (zh) * 2010-05-31 2013-03-27 先正达参股股份有限公司 作为杀虫剂有用的1,8-二氮杂螺[4.5]癸烷-2,4-二酮衍生物
ES2734235T3 (es) * 2013-03-05 2019-12-04 Bayer Cropscience Ag Uso de combinaciones que comprenden cloquintocet-mexilo para la mejora del rendimiento en plantas
ES2879826T3 (es) 2015-06-15 2021-11-23 Nmd Pharma As Compuestos para su uso en el tratamiento de trastornos neuromusculares
US11730714B2 (en) 2017-12-14 2023-08-22 Nmd Pharma A/S Compounds for the treatment of neuromuscular disorders
US11147788B2 (en) 2017-12-14 2021-10-19 Nmd Pharma A/S Compounds for the treatment of neuromuscular disorders

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WO2003029213A1 (fr) * 2001-09-24 2003-04-10 Bayer Cropscience Ag 4-cetolactames et 4-cetolactones 3-phenyl-3-substitues spirocycliques
WO2004037749A2 (fr) * 2002-10-22 2004-05-06 Bayer Cropscience Aktiengesellschaft 1,3-dicetones substitues par 2-phenyle en position 2
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WO2003029213A1 (fr) * 2001-09-24 2003-04-10 Bayer Cropscience Ag 4-cetolactames et 4-cetolactones 3-phenyl-3-substitues spirocycliques
WO2004037749A2 (fr) * 2002-10-22 2004-05-06 Bayer Cropscience Aktiengesellschaft 1,3-dicetones substitues par 2-phenyle en position 2
WO2004064520A1 (fr) * 2003-01-20 2004-08-05 Bayer Cropscience Aktiengesellschaft Herbicides selectifs a base de composes dicarbonyle cycliques substitues et de phytoprotecteurs

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Publication number Priority date Publication date Assignee Title
WO2009150093A1 (fr) 2008-06-11 2009-12-17 Syngenta Participations Ag Nouveaux herbicides
US8623907B2 (en) 2008-06-11 2014-01-07 Syngenta Participations, Ag Herbicides
US10743535B2 (en) 2017-08-18 2020-08-18 H&K Solutions Llc Insecticide for flight-capable pests

Also Published As

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MX2007000636A (es) 2009-02-11
JP2008506739A (ja) 2008-03-06
DE102004035131A1 (de) 2006-02-16
CN101001529A (zh) 2007-07-18
CN100502655C (zh) 2009-06-24
AU2005263566A1 (en) 2006-01-26
BRPI0513502A (pt) 2008-05-06
CN101530101A (zh) 2009-09-16
EP1773126A1 (fr) 2007-04-18
CA2574199A1 (fr) 2006-01-26
EA200700316A1 (ru) 2007-06-29
KR20070039140A (ko) 2007-04-11

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