Microbiocidal phenylamidine derivatives

Patent metadata

Field	Value
Publication number	US-10925283-B2
Application number	US-201716461323-A
Country	US
Kind code	B2
Filing date	Nov 14, 2017
Priority date	Nov 15, 2016
Publication date	Feb 23, 2021
Grant date	Feb 23, 2021

Abstract

Compounds of the formula (I), wherein R 1 , R 2 , R 3 , R 4 and R 5 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

The invention 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 6 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 which may optionally contain one oxygen or one sulphur atom;
R 3 is hydrogen, halogen, C 1 -C 4 alkyl or C 3 -C 6 cycloalkyl;
R 4 is C 1 -C 4 haloalkyl;
R 5 is C 3 -C 8 cycloalkyl wherein the cycloalkyl is substituted with 1 to 3 substituents independently selected from cyano, halogen, C 1 -C 6 alkoxy, C 1 -C 4 haloalkoxy, C 3 -C 6 cycloalkyloxy, C 3 -C 6 alkenyloxy, C 3 -C 6 alkynyloxy, aryloxy, ═N—OR 9 ; or
R 5 is C 3 -C 8 cycloalkyl wherein the cyclic group contains one or two non-contiguous oxygen or sulfur atoms or where one of the ring members represents SO or SO 2 ; or
R 5 is C 1 -C 6 alkyloxycarbonyl; or
R 5 is C 1 -C 6 alkyl wherein the alkyl is substituted with 1 or 2 substituents independently selected from cyano, C 1 -C 6 alkoxy, C 1 -C 6 alkoxy(C 1 -C 6 )alkyloxy, C 1 -C 4 haloalkoxy, C 3 -C 6 cycloalkyloxy (wherein the cycloalkyl group optionally contains one or two non-contiguous oxygen or sulfur atoms or where one of the ring members optionally represents SO or SO 2 and wherein the cycloalkyl group is optionally substituted with one to four groups independently selected from halogen, C 1 -C 6 alkyl, C 1 -C 6 alkyoxy, C 1 -C 6 haloalkyl, C 1 -C 6 haloalkoxy and/or one phenyl (where the phenyl is itself optionally substituted with halogen)), C 3 -C 6 cycloalkyl(C 1 -C 6 )alkyloxy (wherein the cycloalkyl group optionally contains one or two non-contiguous oxygen or sulfur atoms or where one of the ring members optionally represents SO or SO 2 and wherein the cycloalkyl group is optionally substituted with one to four groups independently selected from halogen, C 1 -C 6 alkyl, C 1 -C 6 alkyoxy, C 1 -C 6 haloalkyl, C 1 -C 6 haloalkoxy and/or one phenyl (where the phenyl is itself optionally substituted with halogen)), benzocyclopentanyloxy, benzocyclohexanyloxy, C 3 -C 6 alkenyloxy, C 3 -C 6 alkynyloxy, C 1 -C 4 alkylthio, C 1 -C 4 haloalkylthio, C 3 -C 6 cycloalkylthio, C 1 -C 4 alkylsulphonyl, arylsulphonyl (wherein the aryl is optionally substituted with one to three R 6 groups), aryl(C 1 -C 4 )alkylsulphonyl (wherein the aryl is optionally substituted with one to three R 6 groups), arylthio (wherein the aryl is optionally substituted with one to three R 6 groups), aryl(C 1 -C 4 )alkylthio (wherein the aryl is optionally substituted with one to three R 6 groups), aryloxy (wherein the aryl is optionally substituted with one to three R 6 groups), heteroaryloxy (wherein the heteroaryl is optionally substituted with one to four R 6 groups), Si(C 1 -C 4 alkyl) 3 C 1 -C 4 alkoxy, aryl(C 1 -C 4 )alkyloxy (wherein the aryl is optionally substituted with one to three R 6 groups), heteroaryl(C 1 -C 4 )alkyloxy (wherein the heteroaryl is optionally substituted with one to three R 6 groups), ═N—OR 9 , —O—N═C(R 7 )(R 8 ), —O—(C 1 -C 6 alkyl)-O—N═C(R 7 )(R 8 ), —N(OR 9 )R 10 ; or
R 5 is —CH 2 C(═N—OR 9 )—C 1 -C 2 alkyl or —CH 2 C(═N—OR 9 )-phenyl;
Each R 6 is independently selected from halogen, cyano, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 3 -C 6 cycloalkyl, C 3 -C 6 halocycloalkyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy, C 3 -C 6 cycloalkyloxy, C 1 -C 4 alkylthio, C 1 -C 4 haloalkylthio, C 3 -C 6 cycloalkylthio, C 1 -C 4 alkylsulfinyl, C 1 -C 4 haloalkylsulfinyl, C 1 -C 4 alkylsulfonyl, C 1 -C 4 haloalkylsulfonyl, C 1 -C 4 alkylcarbonyl, C 2 -C 6 alkenyl, C 2 -C 6 haloalkenyl, C 2 -C 6 alkenyloxy, C 2 -C 6 haloalkenyloxy, C 2 -C 6 alkynyl, C 3 -C 6 cycloalkylC 2 -C 6 alkynyl, C 2 -C 6 alkynyloxy, aryl, aryloxy, heteroaryl, heteroaryloxy;
R 7 and R 8 are each independently selected from hydrogen, C 1 -C 4 alkyl, aryl (wherein the aryl is optionally substituted with one to three R 6 groups) and C 3 -C 8 cycloalkyl; or
R 7 and R 8 together with the carbon atom to which they are attached form a four to eight-membered saturated cyclic group which may optionally contain one oxygen or one sulphur atom;
R 9 is C 1 -C 6 alkyl, C 3 -C 6 alkenyl, C 3 -C 6 alkynyl, aryl(C 1 -C 4 )alkyl or C 3 -C 8 cycloalkyl; and
R 10 is C 1 -C 6 alkyl, C 3 -C 6 alkenyl, C 3 -C 6 alkynyl, aryl(C 1 -C 4 )alkyl, aryl or C 3 -C 8 cycloalkyl; or
R 9 and R 10 together with the nitrogen and oxygen atom to which they are attached form a four to six-membered saturated cyclic group;
or an enantiomer, salt or N-oxide thereof.

2. A compound according to claim 1 wherein R 1 and R 2 are each independently selected from C 1 -C 4 alkyl and C 3 -C 6 cycloalkyl.

3. A compound according to claim 1 wherein R 3 is hydrogen, halogen, C 1 -C 4 alkyl or C 3 -C 6 cycloalkyl.

4. A compound according to claim 1 wherein R 4 is C 1 -C 3 haloalkyl.

5. A compound according to claim 1 wherein R 5 is C 3 -C 8 cycloalkyl wherein the cycloalkyl is substituted with 1 to 3 substituents independently selected from cyano, halogen, C 1 -C 6 alkoxy, C 1 -C 4 haloalkoxy, C 3 -C 6 cycloalkyloxy, C 3 -C 6 alkenyloxy, C 3 -C 6 alkynyloxy, phenyloxy, ═N—OR 9 ; or R 5 is C 1 -C 6 alkyl wherein the alkyl is substituted with 1 to 2 substituents independently selected from cyano, C 1 -C 6 alkoxy, C 1 -C 4 haloalkoxy, C 3 -C 6 cycloalkyloxy, C 3 -C 6 alkenyloxy, C 3 -C 6 alkynyloxy, phenyloxy (wherein the phenyl is optionally substituted with one to three R 6 groups), pyridinyloxy (wherein the pyridinyl is optionally substituted with one or two R 6 groups), Si(C 1 -C 4 alkyl) 3 C 1 -C 4 alkoxy, phenyl(C 1 -C 4 )alkyloxy (wherein the phenyl is optionally substituted with one to three R 6 groups), ═N—OR 9 , —O—N═C(R 7 )(R 8 ), —N(OR 9 )R 10 ; wherein each R 6 is independently selected from fluoro, chloro, cyano, C 1 -C 3 alkyl, C 1 -C 2 haloalkyl, C 3 -C 6 cycloalkyl, C 3 -C 6 halocycloalkyl, C 1 -C 3 alkoxy, C 1 -C 3 haloalkoxy, C 3 -C 6 cycloalkyloxy, C 1 -C 3 alkylthio, C 1 -C 3 haloalkylthio, C 3 -C 6 cycloalkylthio, C 1 -C 3 alkylsulfinyl, C 1 -C 3 haloalkylsulfinyl, C 1 -C 3 alkylsulfonyl, C 1 -C 3 haloalkylsulfonyl, C 1 -C 3 alkylcarbonyl, C 2 -C 4 alkenyl, C 2 -C 4 haloalkenyl, C 2 -C 4 alkenyloxy, C 2 -C 4 haloalkenyloxy, C 2 -C 4 alkynyl, C 3 -C 6 cycloalkylC 2 -C 4 alkynyl, C 2 -C 4 alkynyloxy, phenyl, phenyloxy; R 7 and R 8 are each independently selected from hydrogen, C 1 -C 4 alkyl, phenyl (wherein the phenyl is optionally substituted with one or two R 6 groups) and C 3 -C 8 cycloalkyl or R 7 and R 8 together with the carbon atom to which they are attached form a four- to six-membered saturated cyclic group which may optionally contain one oxygen or one sulphur atom; or
R 5 is —CH 2 C(═N—OR 9 )—C 1 -C 2 alkyl or —CH 2 C(═N—OR 9 )-phenyl;
R 9 is C 1 -C 6 alkyl or phenyl(C 1 -C 4 )alkyl and R 10 is C 1 -C 6 alkyl, pheyl(C 1 -C 4 )alkyl, phenyl or C 3 -C 6 cycloalkyl or R 9 and R 10 together with the nitrogen and oxygen atoms to which they are attached form a five- to six-membered saturated cyclic group.

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

7. A compound according to claim 1 wherein R 3 is hydrogen, fluoro, methyl, ethyl, or cyclopropyl.

8. A compound according to claim 1 wherein R 4 is trifluoromethyl, pentafluoroethyl or chlorodifluoromethyl.

9. A compound according to claim 1 wherein R 5 is C

Assignees

• Syngenta Participations Ag

Inventors

• Weiss Matthias
• Sulzer-Mosse Sarah

Classifications

• C07C2602/08

  the other ring being five-membered, e.g. indane · CPC title

• C07C257/12

  having carbon atoms of amidino groups bound to hydrogen atoms · CPC title

• C07C317/28

  with sulfone or sulfoxide groups bound to acyclic carbon atoms of the carbon skeleton · CPC title

• A01N43/20

  three- or four-membered rings · CPC title

• C07D307/42

  Singly bound oxygen atoms · CPC title