Pesticidal compounds

Patent metadata

Field	Value
Publication number	US-9497965-B2
Application number	US-201214354185-A
Country	US
Kind code	B2
Filing date	Oct 31, 2012
Priority date	Nov 4, 2011
Publication date	Nov 22, 2016
Grant date	Nov 22, 2016

Abstract

A compound of formula (I) wherein R1 to R4 are, for example, each hydrogen, R5 is, for example, a substituted phenol; R6 is, for example, hydrogen; R7 is, for example, hydrogen, cyano, hydroxyl, formyl, C1-C4-alkyl, C1-C4-alkoxy, C2-C4-alkenyl, or C2-C4-alkynyl; and A1 to A5 is, for example, A1 is N or C—X, A3 is C—X, and A2, A4 and A5 are C—H, where X, is, for example, halogen; and its use as a pesticidal agent.

First claim

The invention claimed is:

1. A compound of the formula (I) wherein

wherein
R1 is hydrogen, methyl or a halogen;
R2 is hydrogen, methyl or a halogen;
R3 is hydrogen, methyl or a halogen;
R4 is hydrogen, methyl or a halogen;
R5 is substituted or unsubstituted phenyl group;
R6 is hydrogen or C1-C4-alkyl;
R7 is hydrogen, cyano, hydroxyl, formyl, C1-C4-alkyl, C1-C4-alkoxy, C2-C4-alkenyl, C2-C4-alkynyl, C1-C4-alkoxy-C1-C4-alkyl, C1-C4-cyanoalkyl, C1-C4-alkylcarbonyl, C1-C4-alkoxycarbonyl, benzyl, C3-C6-cycloalkylcarbonyl or C3-C6-cycloalkoxycarbonyl;
A1 is C—X, A2, A3 and A4 are C—H, and A5 is N;
X is a halogen, OH, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy or C1-C4-haloalkoxy.

2. The compound according to claim 1 wherein R5 is a substituted phenyl having substituents independently selected from halogen, cyano, C1-C2-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C3-C6-cycloalkyl, which cycloalkyl is unsubstituted or substituted by one or more substituents Rx, where Rx is, independently of each other, is selected from halogen, C1-C4-alkyl, and C1-C4-haloalkyl.

3. The compound according to claim 2 wherein the substituents on the phenyl at R5 are independently selected from halogen, cyano, C1-C4-haloalkyl, C1-C4-haloalkoxy, and C3-C6-cycloalkyl, which cycloalkyl is unsubstituted or substituted by one or more substituents Rx, where Rx is, independently of each other, is selected from halogen, C1-C2-alkyl, and C1-C2 haloalkyl.

4. A composition comprising a compound defined in claim 1 and an agronomic carrier and optionally one or more customary formulation auxiliaries.

5. The composition according to claim 4 further comprising one or more other biologically active compounds.

6. A treated plant propagation material, wherein adhered to the plant propagation material is an effective amount of a compound of formula (I) as defined in claim 1 .

7. The compound according to claim 1 wherein A1 is C—X, A2, A3 and A4 are C—H, and A5 is N.

8. The compound according to claim 1 wherein R5 is a substituted phenyl having one to three substituents.

9. The compound according to claim 8 wherein the substituents are independently selected from chlorine, methyl, fluorine, trifuoromethyl, cyclopropyl, and cyano.

10. The compound according to claim 1 wherein R6 is hydrogen or C1-C2-alkyl.

11. The compound according to claim 1 wherein R7 is hydrogen.

12. The compound according to claim 1 wherein X in CX of the A1 to A5 is, independently selected, from halogen, C1-C2-alkyl and C1-C2-haloalkyl.

13. The compound according to claim 12 wherein X in CX of the A1 to A5 is independently selected from chlorine, fluorine, methyl, and trifluoromethyl.

14. A method for protecting plant propagation material from damage and/or yield loss caused by a pest and/or fungi which comprises applying to the propagation material or site, where the propagation material is planted, an effective amount of a compound of formula (I) as defined in claim 1 .

15. A treated plant propagation material, wherein adhered to the plant propagation material is an effective amount of a compound of formula (I) as defined in claim 1 .

16. A pharmaceutical composition for the control of helminths, arachnids or arthropendo- or ectoparasites which comprises a compound of formula (I) as defined in claim 1 , a physiologically tolerable carrier and optionally one or more customary formulation auxiliaries.

17. A method for the preparation of a composition for treating, controlling, preventing or protecting warm-blooded animals or fish against infestation or infection by helminths, arachnids or arthropendo- or ectoparasites which comprises a compound of formula (I) as defined in claim 1 .

18. A process for preparing a compound of formula (I) comprising reacting a compound of formula (II) and formula (VII)

wherein R1 to R7, A1, A2, A3, A4, and A5 are as defined in claim 1 , and Xb is a leaving group selected from halide and hydroxyl.

Assignees

• Syngenta Participations Ag

Inventors

• Loiseleur Olivier
• Pitterna Thomas
• O'Sullivan Anthony Cornelius
• Luksch Torsten
• Kickova Anna

Classifications

• A61P33/00

  Antiparasitic agents · CPC title

• A61P33/14

  Ectoparasiticides, e.g. scabicides · CPC title

• A01N43/54

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

• C07D239/28

  with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms · CPC title

• C07D401/12

  linked by a chain containing hetero atoms as chain links · CPC title