Carboxamide compounds

Patent metadata

Field	Value
Publication number	US-9738595-B2
Application number	US-201414770557-A
Country	US
Kind code	B2
Filing date	Jan 31, 2014
Priority date	Feb 27, 2013
Publication date	Aug 22, 2017
Grant date	Aug 22, 2017

Abstract

Compounds of the formula (I), in which the substituents are as defined in claim 1 , are suitable for use as nematicides.

First claim

The invention claimed is:

1. A compound of the formula I

wherein
Y is C—H, C—F, C—Cl or N,
A1, A2, A4 and A5 are, independently of each other, N, CH or CR6,
where the number of N atoms in the ring containing A1, A2, A4 and A5 is 0, 1 or 2,
R6 is, independently of each other, selected from halogen, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, and C1-C4-haloalkoxy,
R1 and R2 are each methyl, or R1 and R2 form together with the carbon atom, to which they are attached, a cyclopropyl or cyclobutyl ring,
R3 is, independently of each other, selected from halogen, cyano, R9, O—R9, NO2, COOR9, CONHR9, CONR9aR9, NHR9, NR9aR9, and NHCOR9,
R8 is, independently of each other, selected from halogen, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, and C1-C4-haloalkoxy,
R9 and R9a are, independently of each other, selected from C1-C4-alkyl, which is unsubstituted or substituted by one or more R10, C2-C6-alkenyl, which is unsubstituted or substituted by one or more R10, C2-C6-alkynyl, which is unsubstituted or substituted by one or more R10, aryl, which is unsubstituted or substituted by one or more R10, or heteroaryl, which is unsubstituted or substituted by one or more R10,
R10 is, independently of each other, selected from halogen, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, and C1-C4-haloalkoxy,
p is 0 to 4,
m is 0 to 3,
or a tautomer, an isomer, a diastereomer, or an enantiomer of one of these compounds.

2. The compound according to claim 1 wherein R1 and R2 are each methyl, or R1 and R2 form together with the carbon atom, to which they are attached, a cyclopropyl or cyclobutyl ring.

3. The compound according to claim 1 wherein Y is C—H or N.

4. The compound according to claim 1 , wherein R3 is, independently of each other, selected from a halogen, cyano, C1-C2-alkyl and C1-C2-haloalkyl.

5. The compound according to claim 1 , wherein R8 is, independently selected from, a halogen, cyano, C1-C2-alkyl, or C1-C2-haloalkyl.

6. The compound according to claim 1 , wherein p is 0, 1 or 2.

7. The compound according to claim 1 , wherein m is 0 or 1.

8. A compound of claim 1 of the formula IA

where R6a, R6b, R6d and R6e are independently selected from, hydrogen, halogen, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, and C1-C4-haloalkoxy.

9. A compound of claim 1 of the formula IB

where R6a, R6b, and R6d are, independently selected from, hydrogen, halogen, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, and C1-C4-haloalkoxy.

10. A compound of claim 1 of the formula IC

where R6a, R6b, and R6e are, independently selected from, hydrogen, halogen, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, and C1-C4-haloalkoxy.

11. A pesticidal composition, which, in addition to comprising formulation adjuvants, comprises a nematicidal effective amount of a compound according to claim 1 .

12. A composition according to claim 11 , which further comprises one or more insecticidally, acaricidally, nematicidally and/or fungicidally active agents.

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

14. A pharmaceutical composition comprising a compound defined in claim 1 , a physiologically tolerable carrier, and one or more customary formulation auxiliaries for controlling infection with diseases transmitted through helminths, arachnids or arthropodal endo- or ectoparasites.

15. The composition according to claim 13 further comprising one or more other biologically active compounds.

16. A method of controlling damage and/or yield loss caused by a pest and/or fungi which comprises applying to a pest, to a locus of a pest, or to a plant susceptible to attack by a pest and/or fungi or to a plant propagation material an effective amount of a compound of formula (I) as defined in claim 1 .

17. A method for the 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 the site, where the propagation material is planted, an effective amount of a compound of formula (I) as defined in claim 1 .

18. The method according to claim 16 wherein the damage or loss is caused by a nematode pest.

19. A method of controlling endo- and ectoparasitic nematode infestations and infections in warm-blooded animals, which comprises injecting, topically applying or orally administering a composition according to claim 13 .

20. 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 .

21. A process for the preparation of compounds according to claim 1 by the acylation of an organometallic compound of formula III in which R3, p, R8, m and Y are as defined under formula I in claim 1 , and M(a) is a metal, with a carboxylic acid derivative of formula II in which A1, A2, A4, A5, R1 and R2 are defined in claim 1 , and X(a) is a C1-C6 alkoxy, a hetero-substituted —C1-C6 alkoxy or a heteroatom-substituted dialkylaminyl, in a solvent for between 10 minutes and 5 hours and between −80° C. to 25° C.

Assignees

• Syngenta Participations Ag

Inventors

• Jeanguenat Andre
• Loiseleur Olivier
• Cassayre Jerome Yves
• O'Sullivan Anthony Cornelius

Classifications

• C07C2601/02

  with a three-membered ring · CPC title

• A01N37/18

  containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof · CPC title

• C07C233/76 Primary

  having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by doubly-bound oxygen atoms · CPC title

• 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 · CPC title

• C07C235/46

  having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms · CPC title