IP Library Granted Patent US 11,882,834
Granted Patent B2
US 11,882,834 · App. 16/767,726 · Granted Jan 30, 2024

Microbiocidal thiazole derivatives

Inventors: Martin Pouliot (Stein, CH); Stefano Rendine (Stein, CH)
Assignee: SYNGENTA PARTICIPATIONS AG
A01N43/78C07D417/12
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Quick Facts
Patent No.
US 11,882,834
App. No.
16/767,726
Granted
Jan 30, 2024
Kind
B2
Abstract

Compounds of the formula (I), (I) wherein the substituents are as defined in claim 1 , useful as pesticides, and especially fungicides.

Claims (27)

1. A compound of formula (I):

wherein,

R 1 is fluoro;

R 2 is hydrogen, C 1 -C 4 alkyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkyl, or C 3 -C 4 cycloalkyl;

R 3 is halogen, C 1 -C 4 alkyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkyl, or C 3 -C 4 cycloalkyl;

R 4 is hydrogen;

R 5 is hydrogen, halogen, C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 1 -C 4 haloalkyl, C 2 -C 6 haloalkenyl, C 2 -C 6 haloalkynyl, hydroxyC 1 -C 4 alkyl, cyanoC 1 -C 4 alkyl, C 3 -C 6 cycloalkyl, phenyl or heteroaryl, wherein the heteroaryl moiety is a 5- or 6-membered aromatic monocyclic ring comprising 1, 2, 3 or 4 heteroatoms individually selected from nitrogen, oxygen and sulfur, and wherein the C 3 -C 6 cycloalkyl, phenyl and heteroaryl moieties are each optionally substituted with 1 to 3 groups represented by R 7 ;

R 6 is hydrogen, halogen, C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 1 -C 4 haloalkyl, C 2 -C 6 haloalkenyl, C 2 -C 6 haloalkynyl, hydroxyC 1 -C 4 alkyl, cyanoC 1 -C 4 alkyl, C 3 -C 6 cycloalkyl, phenyl or heteroaryl, wherein the heteroaryl moiety is a 5- or 6-membered aromatic monocyclic ring comprising 1, 2, 3 or 4 heteroatoms individually selected from nitrogen, oxygen and sulfur, and wherein the C 3 -C 6 cycloalkyl, phenyl and heteroaryl moieties are each optionally substituted with 1 to 3 groups represented by R 7 ;

R 7 is halogen, cyano, hydroxyl, C 1 -C 3 alkyl, C 1 -C 3 alkoxy, or C 3 -C 4 cycloalkyl;

X is N;

or a salt or an N-oxide thereof.

2. The compound according to claim 1 , wherein R 2 is hydrogen, methyl, ethyl, methoxy or ethoxy.

3. The compound according to claim 1 , wherein R 3 is halogen or C 1 -C 3 alkyl.

4. The compound according to claim 1 , wherein R 5 is hydrogen, halogen, C 1 -C 6 alkyl, C 2 -C 6 alkynyl, C 3 -C 4 cycloalkyl, or phenyl, wherein the C 3 -C 4 cycloalkyl and phenyl moieties are each optionally substituted with 1 to 3 groups represented by R 7 .

5. The compound according to claim 1 , wherein R 6 is hydrogen, halogen, C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 3 -C 6 cycloalkyl, or phenyl, wherein the heteroaryl moiety is a 5- or 6-membered aromatic monocyclic ring comprising 1, 2, or 3 heteroatoms individually selected from nitrogen, oxygen and sulfur, and wherein the C 3 -C 6 cycloalkyl, phenyl and heteroaryl moieties are optionally substituted with 1 to 3 groups represented by R 7 .

6. The compound according to claim 1 , wherein the compound of formula (I) is 2-[(2,6-difluoro-4-pyridyl)amino]-5-methyl-N(2-methylcyclobutyl)thiazole-4-carboxamide, 2-[(2,6-difluoro-4-pyridyl)amino]-N-(2-ethylcyclobutyl)-5-methyl-thiazole-4-carboxamide, N-(2,2-difluorocyclobutyl)-2-[(2,6-difluoro-4-pyridyl)amino]-5-methyl-thiazole-4-carboxamide, 2-[(2,6-difluoro-4-pyridyl)amino]-N-(2,2-dimethylcyclobutyl)-5-methyl-thiazole-4-carboxamide, or N-(2,2-diethylcyclobutyl)-2-[(2,6-difluoro-4-pyridyl)amino]-5-methyl-thiazole-4-carboxamide.

7. An agrochemical composition comprising a fungicidally effective amount of a compound of formula (I) according to claim 1 .

8. The composition according to claim 7 , further comprising at least one additional active ingredient and/or an agrochemically-acceptable diluent or carrier.

9. A method of controlling or preventing infestation of useful plants by phytopathogenic microorganisms, wherein a fungicidally effective amount of a compound of formula (I) according to claim 1 , or a composition comprising this compound as active ingredient, is applied to the plants, to parts thereof or the locus thereof.

10. The compound according to claim 1 , wherein R 6 is halogen, C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 1 -C 4 haloalkyl, C 2 -C 6 haloalkenyl, C 2 -C 6 haloalkynyl, hydroxyC 1 -C 4 alkyl, cyanoC 1 -C 4 alkyl, C 3 -C 6 cycloalkyl, phenyl or heteroaryl, wherein the heteroaryl moiety is a 5- or 6-membered aromatic monocyclic ring comprising 1, 2, 3 or 4 heteroatoms individually selected from nitrogen, oxygen and sulfur, and wherein the C 3 -C 6 cycloalkyl, phenyl and heteroaryl moieties are each optionally substituted with 1 to 3 groups represented by R 7 .

11. The compound according to claim 6 , wherein the compound is 2-[(2,6-difluoro-4-pyridyl)amino]-5-methyl-N-(2-methylcyclobutyl)thiazole-4-carboxamide.

12. The compound according to claim 6 , wherein the compound is 2-[(2,6-difluoro-4-pyridyl)amino]-N-(2-ethylcyclobutyl)-5-methyl-thiazole-4-carboxamide.

13. The compound according to claim 6 , wherein the compound is N-(2,2-difluorocyclobutyl)-2-[(2,6-difluoro-4-pyridyl)amino]-5-methyl-thiazole-4-carboxamide.

14. The compound according to claim 6 , wherein the compound is 2-[(2,6-difluoro-4-pyridyl)amino]-N-(2,2-dimethylcyclobutyl)-5-methyl-thiazole-4-carboxamide.

15. The compound according to claim 6 , wherein the compound is N-(2,2-diethylcyclobutyl)-2-[(2,6-difluoro-4-pyridyl)amino]-5-methyl-thiazole-4-carboxamide.

16. A method of controlling phytopathogenic microorganisms, comprising: contacting phytopathogenic microorganisms with a compound of formula (I) according to claim 1 .

17. The method according to claim 16 , wherein the compound of formula (I) is selected from

Assignments (2)
MERGER AND CHANGE OF NAME Recorded Feb 28, 2025
From: SYNGENTA PARTICIPATIONS AG; SYNGENTA PARTICIPATIONS AG
To: SYNGENTA CROP PROTECTION AG
Reel/Frame 070362/0665 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 4, 2020
From: PINGEL, ARNE; SCHMITT, NICOLAS; THAYUMANAVAN, ANBU BHARATHI
To: SYNGENTA PARTICIPATIONS AG
Reel/Frame 052834/0096 →