Heterocycle derivatives as pesticides

Patent metadata

Field	Value
Publication number	US-11058115-B2
Application number	US-201816476358-A
Country	US
Kind code	B2
Filing date	Jan 3, 2018
Priority date	Jan 10, 2017
Publication date	Jul 13, 2021
Grant date	Jul 13, 2021

Abstract

The invention relates to novel compounds of the formula (I)

in which X, R 1 , R 2 , R 3 and n have the definitions given above,
to the use thereof as acaricides and/or insecticides for control of animal pests and to processes and intermediates for preparation thereof.

First claim

The invention claimed is:

1. A compound of formula (I)

in which
R 1 is (C 1 -C 6 )alkyl,
R 2 is (C 1 -C 6 )alkyl,
R 3 is optionally singly or multiply, identically or differently substituted (C 3 -C 8 )cycloalkyl, where optional substituents are (C 1 -C 6 )alkyl, (C 1 -C 6 )haloalkyl, (C 1 -C 6 )alkoxy, (C 1 -C 6 )haloalkoxy, halogen or cyano,
X is a heteroaromatic 9-membered or 12-membered fused bicyclic or tricyclic ring system from the group of Q1 to Q18

R 4 is hydrogen, (C 1 -C 6 )alkyl, (C 1 -C 6 )haloalkyl, (C 1 -C 6 )cyanoalkyl, (C 1 -C 6 )hydroxyalkyl, (C 1 -C 6 )alkoxy-(C 1 -C 6 )alkyl, (C 2 -C 6 )alkenyl, or (C 2 -C 6 )alkynyl,
R 5 is hydrogen, C 1 -C 6 )alkyl, (C 1 -C 6 )haloalkyl, (C 1 -C 6 )alkoxy, (C 1 -C 6 )haloalkoxy, (C 1 -C 6 )alkylthio, (C 1 -C 6 )haloalkylthio, (C 1 -C 6 )alkylsulfinyl, (C 1 -C 6 )haloalkylsulfinyl, (C 1 -C 6 )alkylsulfonyl, or (C 1 -C 6 )haloalkylsulfonyl,
R 6 is hydrogen, and
n is 0, 1 or 2.

2. A compound of formula (I) according to claim 1 in which
R 1 is (C 1 -C 4 )alkyl,
R 2 is (C 1 -C 4 )alkyl,
R 3 is optionally singly or multiply, identically or differently substituted (C 3 -C 6 )cycloalkyl, where optional substituents are (C 1 -C 4 )alkyl, (C 1 -C 4 )haloalkyl, (C 1 -C 4 )alkoxy, (C 1 -C 4 )haloalkoxy, halogen or cyano,
X is a heteroaromatic 9-membered or 12-membered fused bicyclic or tricyclic ring system from the group of Q1 to Q18,
R 4 is hydrogen, (C 1 -C 4 )alkyl, (C 1 -C 4 )haloalkyl, (C 1 -C 4 )cyanoalkyl, (C 1 -C 4 )alkoxy-(C 1 -C 4 )alkyl, (C 1 -C 4 )haloalkoxy-(C 1 -C 4 )alkyl, (C 2 -C 4 )alkenyl, or (C 2 -C 4 )alkynyl,
R 5 is hydrogen, C 1 -C 4 )-alkyl, (C 1 -C 4 )-haloalkyl, (C 1 -C 4 )alkoxy, (C 1 -C 4 )haloalkoxy, C 1 -C 4 )alkylthio, (C 1 -C 4 )haloalkylthio, (C 1 -C 4 )alkylsulfinyl, (C 1 -C 4 )haloalkylsulfinyl, (C 1 -C 4 )alkylsulfonyl, or (C 1 -C 4 )haloalkylsulfonyl,
R 6 is hydrogen, and
n is 0, 1 or 2.

3. A compound of formula (I) according to claim 1 in which
R 1 is (C 1 -C 4 )alkyl,
R 2 is (C 1 -C 4 )alkyl,
R 3 is optionally singly or multiply, identically or differently substituted (C 3 -C 6 )cycloalkyl, where optional substituents are (C 1 -C 4 )alkyl, (C 1 -C 4 )haloalkyl, (C 1 -C 4 )alkoxy, (C 1 -C 4 )haloalkoxy, halogen or cyano,
X is a heteroaromatic 9-membered or 12-membered fused bicyclic or tricyclic ring system from the group of Q1, Q2, Q3, Q4, Q5, Q6, Q10, Q11, Q12, Q13, Q14, Q15, Q16, Q17 or Q18,
R 4 is hydrogen, (C 1 -C 4 )alkyl, (C 1 -C 4 )haloalkyl, (C 2 -C 4 )alkenyl, or (C 2 -C 4 )alkynyl,
R 5 is (C 1 -C 4 )alkyl, (C 1 -C 4 )haloalkyl, (C 1 -C 4 )alkoxy, (C 1 -C 4 )haloalkoxy, (C 1 -C 4 )alkylthio, (C 1 -C 4 )haloalkylthio, (C 1 -C 4 )alkylsulfinyl, (C 1 -C 4 )haloalkylsulfinyl, (C 1 -C 4 )alkylsulfonyl, or (C 1 -C 4 )haloalkylsulfonyl, and
n is 0, 1 or 2.

4. A compound of formula (I) according to claim 1 in which
R 1 is methyl, ethyl, n-propyl, or isopropyl,
R 2 is methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, or tert-butyl,
R 3 is optionally singly or doubly, identically or differently substituted cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl, where optional substituents in each case are methyl, ethyl, n-propyl, i-propyl, difluoromethyl, trifluoromethyl,
X is Q1, Q2, Q3, Q13, Q14, or Q15,
R 4 is methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, methoxymethyl or methoxyethyl,
R 5 is fluorine, chlorine, fluoromethyl, difluoromethyl, trifluoromethyl, fluoroethyl, difluoroethyl, trifluoroethyl, tetrafluoroethyl, pentafluoroethyl, trifluoromethoxy, difluorochloromethoxy, dichlorofluoromethoxy, trifluoromethylthio, trifluoromethylsulfonyl or trifluoromethylsulfinyl,
R 6 is hydrogen, cyano, methyl, trifluoromethyl, fluorine or chlorine, and
n is 0, 1 or 2.

5. A compound of formula (I) according to claim 1 in which
R 1 is ethyl,
R 2 is methyl, ethyl or isopropyl,
R 3 is cyclopropyl (unsubstituted) or optionally singly or doubly, identically or differently substituted cyclohexyl, where optional substituents are methyl or trifluoromethyl,
X is Q2, Q3, Q13, Q14 or Q15,
R 4 is methyl,
R 5 is trifluoromethyl, trifluoromethoxy, trifluoromethylthio, trifluoromethylsulfinyl or trifluoromethylsulfonyl,
R 6 is hydrogen,
n is 0 or 2.

6. An agrochemical formulation comprising compound of formula (I) according to claim 1 and one or more extenders and/or surface-active substances.

7. An agrochemical formulation according to claim 6 , additionally comprising a further agrochemically active ingredient.

8. A method of controlling one or more animal pests comprising allowing a compound of formula (I) according to claim 1 or an agrochemical formulation thereof to act on the animal pests and/or a habitat thereof.

9. The compound of formula (I) according to claim 5 , wherein X is Q2.

10. The compound of formula (I) according to claim 5 , wherein X is Q3.

11. The compound of formula (I) according to claim 5 , wherein X is Q13.

12. The compound of formula (I) according to claim 5 , wherein X is Q14.

13. The compound of formula (I) according to claim 5 , wherein X is Q15.

Assignees

• Bayer Ag
• Bayer Cropscience Ag

Inventors

• Wilcke David
• Fischer Ruediger
• Hager Dominik
• Hoffmeister Laura
• Kausch-Busies Nina
• Mosrin Marc
• Willot Matthieu
• Ilg Kerstin
• Goergens Ulrich
• Turberg Andreas

Classifications

• A01N43/90 Primary

  having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system · CPC title

• C07D233/90

  Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals · CPC title

• A01N43/54

  1,3-Diazines; Hydrogenated 1,3-diazines · CPC title

• C07D471/04

  Ortho-condensed systems · CPC title

• C07D487/04

  Ortho-condensed systems · CPC title