Active Compound Combinations Having Insecticidal and Acaricidal Properties

• US 20100048661A1
• Filed: 06/05/2007
• Published: 02/25/2010
• Est. Priority Date: 06/16/2006
• Status: Active Grant

• Current Assignee: Bayer Intellectual Property GmbH (Bayer AG)
• Original Assignee: Bayer Cropscience AG (Bayer AG)
• Inventors: Schnorbach, Hans-Jürgen, Hungenberg, Heike, Thielert, Wolfgang, Nauen, Ralf, Fischer, Reiner
• Granted Patent: US 8,211,931 B2
• Time in Patent Office: Days
• US Class Current: 514/409
• CPC Class Codes: A01N 2300/00 Combinations or mixtures of active ingredients covered by classes A01N27/00 - A01N65/48 with other active or formulation relevant ingredients, e.g. specific carrier materials or surfactants, covered by classes A01N25/00 - A01N65/48
• CPC Class Codes: A01N 43/36 five-membered rings
• CPC Class Codes: A01N 43/38 condensed with carbocyclic rings
• CPC Class Codes: A01N 43/90 having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
• CPC Class Codes: A01N 47/06 containing —O—CO—O— groups; Thio analogues thereof
• CPC Class Codes: A01N 63/14 Insects

Abstract

The novel active compound combinations consisting, firstly, of cyclic ketoenols and, secondly, of beneficial species (natural enemies) have very good insecticidal and/or acaricidal properties.

Claims

1. An active compound/beneficial species combination, comprising one or more compounds of the formula (I)

in which

X represents 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 represents hydrogen, in each case optionally halogen-substituted alkyl or alkoxyalkyl, or saturated, optionally substituted cycloalkyl in which optionally at least one ring atom is replaced by a heteroatom,

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 which optionally contains at least one heteroatom,

D represents hydrogen or an optionally substituted radical selected from the group consisting of alkyl, alkenyl, alkoxyalkyl, and saturated cycloalkyl in which optionally one or more ring members are replaced by heteroatoms, or

A and D together with the atoms to which they are attached represent a saturated or unsaturated cycle which optionally contains at least one heteroatom and is unsubstituted or substituted in the A,D moiety,

G represents hydrogen (a),

in which

E represents a metal ion or an ammonium ion,

L represents oxygen or sulphur,

M represents oxygen or sulphur,

R¹ represents in each case optionally halogen-substituted alkyl, alkenyl, alkoxyalkyl, alkylthioalkyl, or polyalkoxyalkyl, optionally halogen-, alkyl- or alkoxy-substituted cycloalkyl which is optionally interrupted by at least one heteroatom, or in each case optionally substituted phenyl, phenylalkyl, heteroaryl, phenoxyalkyl or heteroaryloxyalkyl,

R² represents in each case optionally halogen-substituted alkyl, alkenyl, alkoxyalkyl, or polyalkoxyalkyl, or represents in each case optionally substituted cycloalkyl, phenyl or benzyl,

R³ represents optionally halogen-substituted alkyl or optionally substituted phenyl,

R⁴ and R⁵ independently of one another represent in each case optionally halogen-substituted alkyl, alkoxy, alkylamino, dialkylamino, alkylthio, alkenylthio, or cycloalkylthio, or represent in each case optionally substituted phenyl, benzyl, phenoxy or phenylthio, and

R⁶ and R⁷ independently of one another represent hydrogen, in each case optionally halogen-substituted alkyl, cycloalkyl, alkenyl, alkoxy, or alkoxyalkyl, optionally substituted phenyl, or optionally substituted benzyl, or R⁶ and R⁷ together with the nitrogen atom to which they are attached represent an optionally substituted ring which is optionally interrupted by oxygen or sulphur, and one or more beneficial species selected from the orders or sub-orders of the Araneae, Acari, Hymenoptera, Coleoptera, Neuroptera, Tysanoptera, Heteroptera, Diptera, Hemiptera, Dermaptera or Parasitiformes.

2. The combination according to claim 1, wherein, in the compound of the formula (I),

W represents hydrogen, C₁-C₄-alkyl, C₁-C₄-alkoxy, chlorine, bromine or fluorine,

X represents C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkyl, fluorine, chlorine or bromine,

Y and Z independently of one another represent hydrogen, C₁-C₄-alkyl, halogen, C₁-C₄-alkoxy or C₁-C₄-haloalkyl,

A represents hydrogen or in each case optionally halogen-substituted C₁-C₆-alkyl or C₃-C₈-cycloalkyl,

B represents hydrogen, methyl or ethyl, or

A and B together with the carbon atom to which they are attached represent saturated C₃-C₆-cycloalkyl in which optionally one ring member is replaced by oxygen or sulphur and which is optionally substituted by one or two substituents selected from the group consisting of C₁-C₄-alkyl, trifluoromethyl and C₁-C₄-alkoxy,

D represents hydrogen, or in each case optionally fluorine- or chlorine-substituted C₁-C₆-alkyl, C₃-C₄-alkenyl or C₃-C₆-cycloalkyl, or

A and D together represent in each case optionally methyl-substituted C₃-C₄-alkanediyl in which optionally one methylene group is replaced by sulphur,

G represents hydrogen (a),

in which

E represents a metal ion or an ammonium ion,

L represents oxygen or sulphur,

M represents oxygen or sulphur,

R¹ represents in each case optionally halogen-substituted C₁-C₁₀-alkyl, C₂-C₁₀-alkenyl, C₁-C₄-alkoxy-C₁-C₄-alkyl, or C₁-C₄-alkylthio-C₁-C₄-alkyl, or optionally fluorine-, chlorine-, C₁-C₄-alkyl- or C₁-C₂-alkoxy-substituted C₃-C₆-cycloalkyl, represents optionally fluorine-, chlorine-, bromine-, cyano-, nitro-, C₁-C₄-alkyl-, C₁-C₄-alkoxy-, trifluoromethyl- or trifluoromethoxy-substituted phenyl, or represents in each case optionally chlorine- or methyl-substituted pyridyl or thienyl,

R² represents in each case optionally fluorine- or chlorine-substituted C₁-C₁₀-alkyl, C₂-C₁₀-alkenyl, or C₁-C₄-alkoxy-C₂-C₄-alkyl,

represents optionally methyl- or methoxy-substituted C₅-C₆-cycloalkyl, or represents in each case optionally fluorine-, chlorine-, bromine-, cyano-, nitro-, C₁-C₄-alkyl-, C₁-C₄-alkoxy-, trifluoromethyl- or trifluoromethoxy-substituted phenyl or benzyl,

R³ represents optionally fluorine-substituted C₁-C₄-alkyl or represents optionally fluorine-, chlorine-, bromine-, C₁-C₄-alkyl-, C₁-C₄-alkoxy-, trifluoromethyl-, trifluoromethoxy-, cyano- or nitro-substituted phenyl,

R⁴ represents in each case optionally fluorine- or chlorine-substituted C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₄-alkylamino, or C₁-C₄-alkylthio, or represents in each case optionally fluorine-, chlorine-, bromine-, nitro-, cyano-, C₁-C₄-alkoxy-, trifluoromethoxy-, C₁-C₄-alkylthio-, C₁-C₄-haloalkylthio-, C₁-C₄-alkyl- or trifluoromethyl-substituted phenyl, phenoxy or phenylthio,

R⁵ represents C₁-C₄-alkoxy or C₁-C₄-thioalkyl,

R⁶ represents C₁-C₆-alkyl, C₃-C₆-cycloalkyl, C₁-C₆-alkoxy, C₃-C₆-alkenyl, or C₁-C₄-alkoxy-C₁-C₄-alkyl,

R⁷ represents C₁-C₆-alkyl, C₃-C₆-alkenyl or C₁-C₄-alkoxy-C₁-C₄-alkyl, and

R⁶ and R⁷ together represent an optionally methyl- or ethyl-substituted C₃-C₆-alkylene radical in which optionally one carbon atom is replaced by oxygen or sulphur.

3. The combination according to claim 1, wherein, in the compound of the formula (I),

W represents hydrogen, methyl, ethyl, chlorine, bromine or methoxy,

X represents chlorine, bromine, methyl, ethyl, propyl, isopropyl, methoxy, ethoxy or trifluoromethyl,

Y and Z independently of one another represent hydrogen, fluorine, chlorine, bromine, methyl, ethyl, propyl, isopropyl, trifluoromethyl or methoxy,

A represents methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, cyclopropyl, cyclopentyl or cyclohexyl,

B represents hydrogen, methyl or ethyl, or

A and B together with the carbon atom to which they are attached represent saturated C₆-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 represents hydrogen, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, allyl, cyclopropyl, cyclopentyl or cyclohexyl, or

A and D together represent optionally methyl-substituted C₃-C₄-alkanediyl,

G represents hydrogen (a),

in which

M represents oxygen or sulphur,

R¹ represents C₁-C₈-alkyl, C₂-C₄-alkenyl, methoxymethyl, ethoxymethyl, ethylthiomethyl, cyclopropyl, cyclopentyl or cyclohexyl,

represents optionally fluorine-, chlorine-, bromine-, cyano-, nitro-, methyl-, ethyl-, methoxy-, trifluoromethyl- or trifluoromethoxy-substituted phenyl, or represents in each case optionally chlorine- or methyl-substituted pyridyl or thienyl,

R² represents C₁-C₈-alkyl, C₂-C₄-alkenyl, methoxyethyl, ethoxyethyl, phenyl or benzyl, and

R⁶ and R⁷ independently of one another represent methyl or ethyl, or R⁶ and R⁷ together represent a C₅-alkylene radical in which the C₃-methylene group is replaced by oxygen.

4. The combination according to claim 1, wherein, in the compound of the formula (I),

W represents hydrogen or methyl,

X represents chlorine, bromine or methyl,

Y and Z independently of one another represent hydrogen, chlorine, bromine or methyl,

A and B together with the carbon atom to which they are attached represent saturated C₆-cycloalkyl in which optionally one ring member is replaced by oxygen and which is optionally monosubstituted by methyl, trifluoromethyl, methoxy, ethoxy, propoxy or butoxy,

G represents hydrogen (a),

in which

M represents oxygen or sulphur,

R¹ represents C₁-C₈-alkyl, C₂-C₄-alkenyl, methoxymethyl, ethoxymethyl, ethylthiomethyl, cyclopropyl, cyclopentyl, or cyclohexyl,

represents phenyl which is optionally monosubstituted by fluorine, chlorine, bromine, methyl, methoxy, trifluoromethyl, trifluoromethoxy, cyano or nitro, or represents in each case optionally chlorine- or methyl-substituted pyridyl or thienyl,

R² represents C₁-C₈-alkyl, C₂-C₄-alkenyl, methoxyethyl, ethoxyethyl, phenyl or benzyl, and

R⁶ and R⁷ independently of one another represent methyl or ethyl, or R⁶ and R⁷ together represent a C₅-alkylene radical in which the C₃-methylene group is replaced by oxygen.

5. The combination according to claim 1, comprising a compound having the structure,

wherein W, X, Y, Z, R, and G are defined as follows:

W X Y Z R G H Br H CH₃ OCH₃ CO-i-C₃H₇ H Br H CH₃ OCH₃ CO₂—

C₂H₅ H CH₃ H CH₃ OCH₃ H H CH₃ H CH₃ OCH₃ CO₂—

C₂H₅ CH₃ CH₃ H Br OCH₃ H CH₃ CH₃ H Cl OCH₃ H H Br CH₃ CH₃ OCH₃ CO-i-C₃H₇ H CH₃ Cl CH₃ OCH₃ CO₂C₂H₅ CH₃ CH₃ CH₃ CH₃ OCH₃ H CH₃ CH₃ H Br OC₂H₅ CO-i-C₃H₇ H CH₃ CH₃ CH₃ OC₂H₅ CO-n-C₃H₇ H CH₃ CH₃ CH₃ OC₂H₅ CO-i-C₃H₇ H CH₃ CH₃ CH₃ OC₂H₅ CO-c-C₃H₅

6. The combination according to claim 1, comprising the compound of the formula (I-3′

)

7. The combination according to claim 1, comprising the compound of the formula (I-4′

)

8. The combination according to claim 1, comprising the compound of the formula (I-4)

10. A method for controlling animal pests, comprising contacting animal pests or their habitat with an active compound/beneficial species combination according to claim 1.

11. A process for preparing an insecticidal or an acaricidal composition, comprising mixing an active compound/beneficial species combination according to claim 1 with one or more extenders, surfactants, or combinations thereof.

12. A method for reducing spray applications (number of applications per season), comprising contacting animal pests or their habitat with an active compound/beneficial species combination according to claim 1.

13. A method for reducing the total insecticide or acaricide residues on harvested material and in the environment, comprising contacting animal pests or their habitat with an active compound/beneficial species combination according to claim 1.

14. A composition, comprising an active compound/beneficial species combination according to claim 1 and one or more extenders, surfactants, or combinations thereof.

9. (canceled)