Microbiocidal phenylamidine derivatives

Patent metadata

Field	Value
Publication number	US-10934265-B2
Application number	US-201816769835-A
Country	US
Kind code	B2
Filing date	Nov 29, 2018
Priority date	Dec 4, 2017
Publication date	Mar 2, 2021
Grant date	Mar 2, 2021

Abstract

Compounds of the formula (I) wherein the subsitiuents are as defined in claim 1. Furthermore, the present invention relates to agrochemical compositions which comprise compounds of formula (I), to preparation of these compositions, and to the use of the compounds or compositions in agriculture or horticulture for combating, preventing or controlling infestation of plants, harvested food crops, seeds or non-living materials by phytopathogenic microorganisms, in particular fungi.

First claim

What is claimed is:

1. A compound of formula (I)

wherein
R 1 and R 2 are each independently selected from C 1 -C 4 alkyl and C 3 -C 8 cycloalkyl; or
R 1 and R 2 together with the nitrogen atom to which they are attached form a three- to six-membered saturated cyclic group;
R 3 is hydrogen, halogen or C 1 -C 4 alkyl;
R 4 and R 5 are each independently selected from hydrogen and C 1 -C 4 alkyl; or
R 4 and R 5 together with the carbon atom to which they are attached form a carbonyl group (C═O);
X is O, S or NCH 3 ;
n is 0 or 1;
or a salt, metal complex, stereoisomer or N-oxide thereof.

2. A compound according to claim 1 wherein R 1 and R 2 are each independently C 1 -C 4 alkyl.

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

4. A compound according to claim 1 wherein R 4 and R 5 are each independently selected from hydrogen and methyl, or R 4 and R 5 together with the carbon atom to which they are attached form a carbonyl group.

5. A compound according to claim 1 wherein R 1 and R 2 are each independently selected from methyl, ethyl and isopropyl.

6. A compound according to claim 1 wherein R 3 is fluoro, chloro or methyl.

7. A compound according to claim 1 wherein R 4 and R 5 are both hydrogen, or R 4 and R 5 together with the carbon atom to which they are attached form a carbonyl group.

8. A compound according to claim 1 wherein R 1 is methyl, ethyl or isopropyl and R 2 is methyl or ethyl.

9. A compound according to claim 1 wherein R 3 is chloro or methyl and R 4 and R 5 are both hydrogen.

10. A compound according to claim 1 wherein
R 1 and R 2 are each independently selected from methyl, ethyl and isopropyl;
R 3 is fluoro, chloro or methyl;
R 4 and R 5 are both hydrogen, or R 4 and R 5 together with the carbon atom to which they are attached form a carbonyl group;
X is O, S or NCH 3 ;
n is 0 or 1;
or a salt, metal complex, stereoisomer or N-oxide thereof.

11. A compound according to claim 1 wherein the compound is selected from:

N-ethyl-N′-[5-hydroxy-2-methyl-4-[2-(trifluoromethyl)tetrahydrofuran-2-yl]phenyl]-N-methyl-formamidine;

N′-[5-hydroxy-2-methyl-4-[2-(trifluoromethyl)tetrahydrofuran-2-yl]phenyl]-N-isopropyl-N-methyl-formamidine;

N′-[2-chloro-5-hydroxy-4-[2-(trifluoromethyl)tetrahydrofuran-2-yl]phenyl]-N-ethyl-N-methyl-formamidine;

N-ethyl-N′-[5-hydroxy-2-methyl-4-[4-oxo-2-(trifluoromethyl)tetrahydrofuran-2-yl]phenyl]-N-methyl-formamidine;

N-ethyl-N′-[5-hydroxy-2-methyl-4-[2-(trifluoromethyl)tetrahydrothiophen-2-yl]phenyl]-N-methyl-formamidine; or

N-ethyl-N′-[5-hydroxy-2-methyl-4-[2-(trifluoromethyl)oxetan-2-yl]phenyl]-N-methyl-formamidine;
or a salt, metal complex, stereoisomer or N-oxide thereof.

12. A compound according to claim 1 wherein X is O or S.

13. A composition comprising a fungicidally effective amount of a compound of formula (I) as defined in claim 1 .

14. A composition according to claim 13 , wherein the composition further comprises at least one additional active ingredient and/or a diluent.

15. A method of combating, preventing or controlling phytopathogenic fungi which comprises applying to phytopathogenic fungi, to the locus of phytopathogenic fungi, or to a plant susceptible to attack by phytopathogenic fungi, or to propagation material thereof, a fungicidally effective amount of a compound of formula (I) as defined in claim 1 .

16. A method of combating, preventing or controlling phytopathogenic fungi which comprises applying to phytopathogenic fungi, to the locus of phytopathogenic fungi, or to a plant susceptible to attack by phytopathogenic fungi, or to propagation material thereof, a composition comprising a fungicidally effective amount of a compound of formula (I) as defined in claim 1 .

Assignees

• Syngenta Participations Ag

Inventors

• Sulzer-Mosse Sarah
• Pinson Benjamin

Classifications

• A01N43/08

  with oxygen as the ring hetero atom · CPC title

• A01N43/20

  three- or four-membered rings · CPC title

• C07D307/06

  with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to ring carbon atoms · CPC title

• C07D305/06 Primary

  with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring atoms · CPC title

• C07D307/20

  Oxygen atoms · CPC title