Compounds

Patent metadata

Field	Value
Publication number	US-9408392-B2
Application number	US-201314375801-A
Country	US
Kind code	B2
Filing date	Feb 14, 2013
Priority date	Feb 14, 2012
Publication date	Aug 9, 2016
Grant date	Aug 9, 2016

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 Ic

wherein
A2, A3, A4, and A5 are N, CH, or CR11, provided A3 is either CH or N and only one of A2 to A5 is N;
wherein R11 is, independently of each other, halogen, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-haloalkylsulfanyl, C1-C4-alkoxy-C1-C4-alkyl or C1-C4-haloalkoxy-C1-C4-)alkyl,
R 1 , R 2 and R 3 , independently of each other, are hydrogen, halogen, cyano, C1-C4-alkyl or C1-C4-haloalkyl,
B is a mono- or bicyclic 5 to 10 membered heteroaromatic ring system containing 1 to 5 heteroatoms, each independently selected from oxygen, nitrogen and sulphur, or a mono- or bicyclic 5 to 10 membered aromatic ring system, wherein the heteroaromatic ring system or the aromatic ring system is unsubstituted or substituted by R9, where
R9 is, independently of each other, halogen, cyano, R8, —OR8, —C(O)R8, —OC(O)R8, —NR7R8, —NR7C(O)R8, —NR7S(O)nR8, —S(O)nR8, —S(O)nNR7R8, —C(O)OR8 or C(O)NR7R8, where
n is 0, 1, or 2,
R7 is, independently of each other, hydrogen, C1-C4-alkyl, C1-C4-haloalkyl, benzyl or phenyl, where benzyl or phenyl is unsubstituted or substituted with halogen, cyano, C1-C4-alkyl or C1-C4-haloalkyl, and
R8 is, independently of each other, C1-C4-alkyl, which is unsubstituted or substituted by R10, C3-C6-cycloalkyl, which is unsubstituted or substituted by R10, C6-C14-bicycloalkyl, which is unsubstituted or substituted by R10, C2-C4-alkenyl, which is unsubstituted or substituted by R10, C2-C4-alkynyl, which is unsubstituted or substituted by R10, phenyl, which is unsubstituted or substituted by R10, or heteroaryl, which is unsubstituted or substituted by R10, where
R10 is, independently of each other, hydroxyl, halogen, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkylthio, C1-C4-haloalkylthio, C2-C4-alkenyloxy, C2-C4-alkynyloxy, formyl, C1-C4-alkylcarbonyl, C1-C4alkoxycarbonyl or halophenyl,
wherein B and A-CO—NR5 are cis to each other on the cyclopropyl ring,
and tautomers, enantiomers of these compounds.

2. The compound according to claim 1 wherein R11 is, independently of each other, halogen, cyano, C1-C4-alkyl, or C1-C4-haloalkyl,
R 1 is hydrogen, halogen or C1-C4-alkyl, R 2 and R 3 is, independently of each other, hydrogen or C1-C4-alkyl,
B is a mono- 5 to 10 membered heteroaromatic ring system containing 1 nitrogen atom, or a mono- 5 to 10 membered aromatic ring system, wherein the heteroaromatic ring system or the aromatic ring system is substituted by one or more R9, where R9 is, independently of each other, halogen, cyano, R8, —OR8, —S(O)nR8, where n is 0, 1, or 2,
R8 is, independently of each other, C1-C4-alkyl, which is unsubstituted or substituted by R10, C3-C6-cycloalkyl, which is unsubstituted or substituted by R10, phenyl, which is unsubstituted or substituted by R10 or heteroaryl, which is unsubstituted or substituted by R10, where
R10 is halogen, cyano, or C1-C4-haloalky; provided where R8 is heteroaryl, R10 is halogen, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkylthio, C1-C4-alkylcarbonyl, or C1-C4alkoxycarbonyl,
wherein B and A-CO—NR5 are cis to each other on the cyclopropyl ring.

3. The compound according to claim 2 , wherein A2, A4 and A5 are independently selected from CH or CR11, wherein R11 is independently selected from halogen, cyano, C1-C4-alkyl, or C1-C4-haloalkyl,
R 1 is hydrogen, or halogen,
R 2 and R 3 is, independently of each other, hydrogen or C1-C4-alkyl,
B is a pyridyl or phenyl, which are, independent of each other, is substituted by one or more R9, where
R9 is, independently of each other, selected from halogen, cyano, C1-C4-alkyl, C1-C4-alkoxy, C1-C4-haloalkyl, C1-C4-haloalkoxy, C3-C6-cycloalkyl and C1-C4-haloalkyl-C3-C6-cycloalkyl,
wherein B and A-CO—NR5 are cis to each other on the cyclopropyl ring.

4. A compound of the formula Vb

wherein R19 and R20, independantly of each other, are hydrogen, halogen, cyano, C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, with the proviso that at least one of R19 and R20 is different from hydrogen.

5. A compound of the formula VI

wherein A2, A3, A4, and A5 are as defined in claim 1 .

6. A pesticidal composition, which, in addition to comprising formulation adjuvants, comprises a pesticidal effective amount of a compound of the formula I according to claim 1 .

7. The composition according to claim 6 , which further comprises one or more other biologically active agents.

8. 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 6 .

9. 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 the site, where the propagation material is planted, an effective amount of a compound of formula (I) as defined in claim 6 .

10. The method according to claim 8 wherein the damage or loss is caused by a nematode pest.

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

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

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

14. The composition according to claim 12 further comprising one or more other biologically active compounds.

15. A method of controlling and preventing endo- and ectoparasitic nematode infestations and infections in warm-blooded animals, which comprises injecting, topically applying or orally administering a composition according to claim 12 .

Assignees

• Syngenta Participations Ag

Inventors

• O'Sullivan Anthony Cornelius
• Loiseleur Olivier
• Stierli Daniel
• Luksch Torsten
• Pitterna Thomas

Classifications

• A61P33/10

  Anthelmintics · CPC title

• A61P33/14

  Ectoparasiticides, e.g. scabicides · CPC title

• C07D307/68

  Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen · 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

• C07D213/81

  Amides; Imides · CPC title