US2006051386A1PendingUtilityA1

Combinations of active ingredients, which exhibit insecticidal and acaricidal properties

Assignee: FISCHER REINERPriority: Jun 29, 2000Filed: Oct 3, 2005Published: Mar 9, 2006
Est. expiryJun 29, 2020(expired)· nominal 20-yr term from priority
A61K 31/407A01N 43/38A61K 31/216A01N 43/36
64
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Claims

Abstract

The invention relates to novel active compound combinations having very good insecticidal and acaricidal properties and containing (a) cyclic ketoenols having the formula in which the groups W, X, Y, Z, A, B, D, and G have the meanings given in the disclosure, and (b) the active compounds (1) to (23) listed in the disclosure.

Claims

exact text as granted — not AI-modified
1 - 8 . (canceled)  
   
   
       9 . A composition comprising a mixture of 
 (a) one or more compounds of formula (I)                          in which    X represents halogen, alkyl, alkoxy, halogenoalkyl, halogenoalkoxy, or cyano,    W, Y, and Z independently of one another each represent hydrogen, halogen, alkyl, alkoxy, halogenoalkyl, halogenoalkoxy, or cyano,    A represents hydrogen; optionally halogen-substituted alkyl, or alkoxyalkyl; saturated, optionally substituted cycloalkyl, in which one or more ring atoms are optionally replaced by heteroatoms,    B represents hydrogen or alkyl, or    A and B together with the carbon atom to which they are attached represent a saturated or unsaturated, unsubstituted or substituted cycle that optionally contains one or more heteroatoms,    D represents hydrogen or an optionally substituted radical selected from the group consisting of alkyl, alkenyl, alkoxyalkyl, and saturated cycloalkyl in which one or more ring members are optionally replaced by heteroatoms, or    A and D together with the atoms to which they are attached represent a saturated or unsaturated cycle that is unsubstituted or substituted in the A,D moiety and optionally contains one or more heteroatoms, and    G represents hydrogen (a) or one of the groups                          in which    E represents a metal ion or an ammonium ion,    L represents oxygen or sulphur,    M represents oxygen or sulphur,    R 1  represents optionally halogen-substituted alkyl, alkenyl, alkoxyalkyl, alkylthioalkyl, or polyalkoxyalkyl; optionally halogen-, alkyl-, or alkoxy-substituted cycloalkyl that is optionally interrupted by one or more heteroatoms or optionally substituted phenyl, phenylalkyl, hetaryl, phenoxyalkyl, or hetaryloxyalkyl,    R 2  represents optionally halogen-substituted alkyl, alkenyl, alkoxyalkyl, or polyalkoxyalkyl; or optionally substituted cycloalkyl, phenyl or benzyl,    R 3  represents optionally halogen-substituted alkyl or optionally substituted phenyl,    R 4  and R 5  independently of one another each represent optionally halogen-substituted alkyl, alkoxy, alkylamino, dialkylamino, alkylthio, alkenylthio, or cycloalkylthio; or optionally substituted phenyl, benzyl, phenoxy, or phenylthio, and    R 6  and R 7  independently of one another each represent hydrogen; optionally halogen-substituted alkyl, cycloalkyl, alkenyl, alkoxy, or alkoxyalkyl; optionally substituted phenyl; or optionally substituted benzyl; or R 6  and R 7  together with the N atom to which they are attached represent an optionally substituted ring that is optionally interrupted by oxygen or sulphur, and    (b) at least one compound selected from the group consisting of acrinathrin, alpha-cypermethrin, betacyfluthrin, cyhalothrin, cypermethrin, deltamethrin, esfenvalerate, etofenprox, fenpropathrin, fenvalerate, flucythrinate, lambda-cyhalothrin, permethrin, tau-fluvalinate, tralomethrin, zeta-cypermethrin, cyfluthrin, bifenthrin, cycloprothrin, eflusilanate, fubfenprox, pyrethrin, and resmethrin,    with the proviso that when component (a) is a compound of the formula                          then component (b) cannot be acrinathrin, alpha-cypermethrin, betacyfluthrin, cyhalothrin, cypermethrin, deltamethrin, fenpropathrin, lambda-cyhalothrin, permethrin, zeta-cypermethrin, cyfluthrin, or cycloprothrin.    
   
   
       10 . A composition according to  claim 9  comprising one or more compounds of the formula (I) in which 
 W represents hydrogen, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, chlorine, bromine, or fluorine,    X represents C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -halogenoalkyl, fluorine, chlorine, or bromine,    Y and Z independently of one another each represent hydrogen, C 1 -C 4 -alkyl, halogen, C 1 -C 4 -alkoxy, or C 1 -C 4 -halogenoalkyl,    A represents hydrogen or optionally halogen-substituted C 1 -C 6 -alkyl or C 3 -C 8 -cycloalkyl,    B represents hydrogen, methyl, or ethyl, or    A, B, and the carbon atom to which they are attached represent saturated C 3 -C 6 -cycloalkyl in which one ring member is optionally replaced by oxygen or sulphur and that is optionally mono- or disubstituted by C 1 -C 4 -alkyl, trifluoromethyl, or C 1 -C 4 -alkoxy,    D represents hydrogen or optionally fluorine- or chlorine-substituted C 1 -C 6 -alkyl, C 3 -C 4 -alkenyl, or C 3 -C 6 -cycloalkyl, or    A and D together represent optionally methyl-substituted C 3 -C 4 -alkanediyl in which one methylene group is optionally replaced by sulphur, and    G represents hydrogen (a) or one of the groups                          in which    E represents a metal ion or an ammonium ion,    L represents oxygen or sulphur,    M represents oxygen or sulphur,    R 1  represents optionally halogen-substituted C 1 -C 10 -alkyl, C 2 -C 10 -alkenyl, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, or C 1 -C 4 -alkylthio-C 1 -C 4 -alkyl or optionally fluorine-, chlorine-, C 1 -C 4 -alkyl, or C 1 -C 2 -alkoxy-substituted C 3 -C 6 -cycloalkyl; optionally fluorine-, chlorine-, bromine-, cyano-, nitro-, C 1 -C 4 -alkyl-, C 1 -C 4 -alkoxy-, trifluoromethyl-, or trifluoromethoxy-substituted phenyl; or optionally chlorine- or methyl-substituted pyridyl or thienyl,    R 2  represents optionally fluorine- or chlorine-substituted C 1 -C 10 -alkyl, C 2 -C 10 -alkenyl, or C 1 -C 4 -alkoxy-C 2 -C 4 -alkyl; optionally methyl- or methoxy-substituted C 5 -C 6 -cycloalkyl; or optionally fluorine-, chlorine-, bromine-, cyano-, nitro-, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, triflouromethyl-, or trifluoromethoxy-substituted phenyl or benzyl,    R 3  represents optionally fluorine-substituted C 1 -C 4 -alkyl or optionally fluorine-, chlorine-, bromine-, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, trifluoromethyl, trifluoromethoxy, cyano, or nitro-substituted phenyl,    R 4  represents optionally fluorine- or chlorine-substituted C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -alkylamino, or C 1 -C 4 -alkylthio; or optionally fluorine-, chlorine-, bromine-, nitro-, cyano-, C 1 -C 4 -alkoxy, trifluoromethoxy, C 1 -C 4 -alkylthio, C 1 -C 4 -halogenoalkylthio, C 1 -C 4 -alkyl, or trifluoromethyl-substituted phenyl, phenoxy, or phenylthio,    R 5  represents C 1 -C 4 -alkoxy or C 1 -C 4 -thioalkyl,    R 6  represents C 1 -C 6 -alkyl, C 3 -C 6 -cycloalkyl, C 1 -C 6 -alkoxy, C 3 -C 6 -alkenyl, or C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, and    R 7  represents C 1 -C 6 -alkyl, C 3 -C 6 -alkenyl, or C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, or    R 6  and R 7  together represent an optionally methyl- or ethyl-substituted C 3 -C 6 -alkylene radical in which one carbon atom is optionally replaced by oxygen or sulphur.    
   
   
       11 . A composition according to  claim 9  comprising one or more compounds of the formula (I) in which 
 W represents hydrogen, methyl, ethyl, chlorine, bromine, or methoxy,    X represents chlorine, bromine, methyl, ethyl, propyl, i-propyl, methoxy, ethoxy, or trifluoromethyl,    Y and Z independently of one another each represent hydrogen, fluorine, chlorine, bromine, methyl, ethyl, propyl, i-propyl, trifluoromethyl, or methoxy,    A represents methyl, ethyl, propyl, i-propyl, butyl, i-butyl, sec-butyl, tert-butyl, cyclopropyl, cyclopentyl, or cyclohexyl,    B represents hydrogen, methyl, or ethyl, or    A, B, and the carbon atom to which they are attached represent saturated C 6 -cycloalkyl in which one ring member is optionally replaced by oxygen and that is optionally monosubstituted by methyl, ethyl, methoxy, ethoxy, propoxy, or butoxy,    D represents hydrogen, methyl, ethyl, propyl, i-propyl, butyl, i-butyl, allyl, cyclopropyl, cyclopentyl, or cyclohexyl, or    A and D together represent optionally methyl-substituted C 3 -C 4 -alkanediyl, and    G represents hydrogen (a) or one of the groups                          in which    M represents oxygen or sulphur,    R 1  represents C 1 -C 8 -alkyl, C 2 -C 4 -alkenyl, methoxymethyl, ethoxymethyl, ethylthiomethyl, cyclopropyl, cyclopentyl, or cyclohexyl; optionally fluorine-, chlorine-, bromine-, cyano-, nitro-, methyl-, ethyl-, methoxy-, trifluoromethyl-, or trifluoromethoxy-substituted phenyl; or optionally chlorine- or methyl-substituted pyridyl or thienyl,    R 2  represents C 1 -C 8 -alkyl, C 2 -C 4 -alkenyl, methoxyethyl, ethoxyethyl, phenyl, or benzyl, and    R 6  and R 7  independently of one another represent methyl or ethyl or R 6  and R 7  together represent a C 5 -alkylene radical in which the C 3 -methylene group is replaced by oxygen.    
   
   
       12 . A composition according to  claim 9  comprising one or more compounds of the formula (I) in which 
 X represents hydrogen or methyl,    X represents chlorine, bromine, or methyl,    Y and Z independently of one another each represent hydrogen, chlorine, bromine, or methyl,    A, B, and the carbon atom to which they are attached represent saturated C 6 -cycloalkyl in which one ring member is optionally replaced by oxygen and that is optionally monosubstituted by methyl, methoxy, ethoxy, propoxy, or butoxy,    D represents hydrogen, and    G represents hydrogen (a) or one of the groups                          in which    M represents oxygen or sulphur,    R 1  represents C 1 -C 8 -alkyl, C 2 -C 4 -alkenyl, methoxymethyl, ethoxymethyl, ethylmethylthio, cyclopropyl, cyclopentyl, or cyclohexyl; optionally fluorine-, chlorine-, bromine-, methyl-, methoxy-, trifluoromethyl-, trifluoromethoxy-, cyano-, or nitro-substituted phenyl; or optionally chlorine- or methyl-substituted pyridyl or thienyl,    R 2  represents C 1 -C 8 -alkyl, C 2 -C 4 -alkenyl, methoxyethyl, ethoxyethyl, phenyl, or benzyl, and    R 6  and R 7  independently of one another each represent methyl, ethyl or R 6  and R 7  together represent a C 5 -alkylene radical in which the C 3 -methylene is replaced by oxygen.    
   
   
       13 . A composition according to  claim 9  comprising one or more compounds of the formula (I)  
     
       
         
         
             
             
         
       
     
     in which 
 (1) W is H, X is Br, Y is 5-CH 3 , Z is H, R is OCH 3 , and G is CO-i-C 3 H 7 ;  
 (2) W is H, X is Br, Y is 5-CH 3 , Z is H, R is OCH 3 , and G is CO 2 —C 2 H 5 ;  
 (3) W is H, X is CH 3 , Y is 5-CH 3 , Z is H, R is OCH 3 , and G is H;  
 (4) W is H, X is CH 3 , Y is 5—CH 3 , Z is H, R is OCH 3 , and G is CO 2 —C 2 H 5 ;  
 (5) W is CH 3 , X is CH 3 , Y is 3-Br, Z is H, R is OCH 3 , and G is H;  
 (6) W is CH 3 , X is CH 3 , Y is 3-Cl, Z is H, R is OCH 3 , and G is H;  
 (7) W is H, X is Br, Y is 4-CH 3 , Z is 5-CH 3 , R is OCH 3 , and G is CO-i-C 3 H 7 ;  
 (8) W is H, X is CH 3 , Y is 4-Cl, Z is 5-CH 3 , R is OCH 3 , and G is CO 2 —C 2 H 5 ;  
 (9) W is H, X is CH 3 , Y is 4-CH 3 , Z is 5-CH 3 , R is OCH 3 , and G is  
                     
 (10) W is CH 3 , X is CH 3 , Y is 3—CH 3 , Z is 4-CH 3 , R is OCH 3 , and G is H  
 (11) W is H, X is CH 3 , Y is 5-CH 3 , Z is H, R is OC 2 H 5 , and G is  
                     
 (12) W is CH 3 , X is CH 3 , Y is 3-Br, Z is H, R is OC 2 H 5 , and G is CO-i-C 3 H 7 ;  
 (13) W is H, X is CH 3 , Y is 4-CH 3 , Z is 5-CH 3 , R is OC 2 H 5 , and G is CO-n-Pr;  
 (14) W is H, X is CH 3 , Y is 4-CH 3 , Z is 5-CH 3 , R is OC 2 H 5 , and G is CO-i-Pr; or  
 (15) W is H, X is CH 3 , Y is 4-CH 3 , Z is 5-CH 3 , R is OC 2 H 5 , and G is CO-c-Pr.  
 
   
   
       14 . A method for controlling animal pests comprising allowing an effective amount of a composition comprising a mixture of 
 (a) one or more compounds of formula (I)                          in which    X represents halogen, alkyl, alkoxy, halogenoalkyl, halogenoalkoxy, or cyano,    W, Y, and Z independently of one another each represent hydrogen, halogen, alkyl, alkoxy, halogenoalkyl, halogenoalkoxy, or cyano,    A represents hydrogen; optionally halogen-substituted alkyl, or alkoxyalkyl; saturated, optionally substituted cycloalkyl, in which one or more ring atoms are optionally replaced by heteroatoms,    B represents hydrogen or alkyl, or    A and B together with the carbon atom to which they are attached represent a saturated or unsaturated, unsubstituted or substituted cycle that optionally contains one or more heteroatoms,    D represents hydrogen or an optionally substituted radical selected from the group consisting of alkyl, alkenyl, alkoxyalkyl, and saturated cycloalkyl in which one or more ring members are optionally replaced by heteroatoms, or    A and D together with the atoms to which they are attached represent a saturated or unsaturated cycle that is unsubstituted or substituted in the A,D moiety and optionally contains one or more heteroatoms, and    G represents hydrogen (a) or one of the groups                          in which    E represents a metal ion or an ammonium ion,    L represents oxygen or sulphur,    M represents oxygen or sulphur,    R 1  represents optionally halogen-substituted alkyl, alkenyl, alkoxyalkyl, alkylthioalkyl, or polyalkoxyalkyl; optionally halogen-, alkyl-, or alkoxy-substituted cycloalkyl that is optionally interrupted by one or more heteroatoms or optionally substituted phenyl, phenylalkyl, hetaryl, phenoxyalkyl, or hetaryloxyalkyl,    R 2  represents optionally halogen-substituted alkyl, alkenyl, alkoxyalkyl, or polyalkoxyalkyl; or optionally substituted cycloalkyl, phenyl or benzyl,    R 3  represents optionally halogen-substituted alkyl or optionally substituted phenyl,    R 4  and R 5  independently of one another each represent optionally halogen-substituted alkyl, alkoxy, alkylamino, dialkylamino, alkylthio, alkenylthio, or cycloalkylthio; or optionally substituted phenyl, benzyl, phenoxy, or phenylthio, and    R 6  and R 7  independently of one another each represent hydrogen;    optionally halogen-substituted alkyl, cycloalkyl, alkenyl, alkoxy, or alkoxyalkyl; optionally substituted phenyl; or optionally substituted benzyl; or R 6  and R 7  together with the N atom to which they are attached represent an optionally substituted ring that is optionally interrupted by oxygen or sulphur, and    (b) at least one compound selected from the group consisting of acrinathrin, alpha-cypermethrin, betacyfluthrin, cyhalothrin, cypermethrin, deltamethrin, esfenvalerate, etofenprox, fenpropathrin, fenvalerate, flucythrinate, lambda-cyhalothrin, permethrin, tau-fluvalinate, tralomethrin, zeta-cypermethrin, cyfluthrin, bifenthrin, cycloprothrin, eflusilanate, fubfenprox, pyrethrin, and resmethrin,    to act on animal pests and/or their habitat.    
   
   
       15 . A process for preparing an insecticidal and acaricidal composition comprising mixing a composition according to  claim 9  with extenders and/or surfactants.

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