Ethynylphenylamidine compound or salt thereof, method for producing same, and fungicide for agricultural and horticultural use
An object of the present invention is to provide a novel fungicide having an excellent fungicidal activity. The compound used as the fungicide of the present invention is an ethynylphenylamidine compound or a salt thereof, the compound being represented by Formula (1): wherein R 1 and R 2 are each hydrogen or C 1-12 alkyl, or R 1 and R 2 may be bonded together to form C 1-7 alkylene; R 3 is hydrogen or C 1-4 alkylthio; R 4 , R 5 , R 6 , and R 7 are each hydrogen, halogen, etc.; and R 8 is hydrogen, C 1-20 alkyl, C 3-8 cycloalkyl, C 1-4 haloalkyl, phenyl, a heterocyclic group, or —(CH 2 )n-Si(R 9 )(R 10 )(R 11 ) wherein R 9 , R 10 , and R 11 are each C 1-6 alkyl, and n is an integer of 0 or 1.
1. An ethynylaniline compound represented by Formula (4):
wherein R 4 and R 6 are each halogen or C 1-4 alkyl;
R 5 and R 7 are each hydrogen; and
R 8 is hydrogen; C 1-20 alkyl optionally substituted on the alkyl group with one or more substituents independently selected from the group consisting of C 1-4 alkoxy, hydroxy, cyano, phenyl, phenoxy, and optionally substituted heterocyclic groups; C 3-8 cycloalkyl; C 1-4 haloalkyl; phenyl optionally substituted on the phenyl ring with one to five substituents independently selected from the group consisting of halogen, C 1-6 alkyl, C 1-4 haloalkyl, C 1-4 alkoxy, and phenoxy; a heterocyclic group optionally substituted on the heterocyclic ring with one or more substituents independently selected from the group consisting of halogen, C 1-4 alkyl, C 1-4 haloalkyl, and optionally substituted heterocyclic groups; or —(CH 2 )n-Si(R 9 )(R 10 )(R 11 ) wherein R 9 , R 10 , and R 11 are each C 1-6 alkyl, and n is an integer of 0 or 1.
2. The ethynylaniline compound according to claim 1 , wherein R 8 is C 1-20 alkyl optionally substituted on the alkyl group with one or more substituents independently selected from the group consisting of C 1-4 alkoxy, hydroxy, cyano, phenyl, phenoxy, and optionally substituted heterocyclic groups; C 3-8 cycloalkyl; C 1-4 haloalkyl; phenyl optionally substituted on the phenyl ring with one to five substituents independently selected from the group consisting of halogen, C 1-6 alkyl, C 1-4 haloalkyl, C 1-4 alkoxy, and phenoxy; a heterocyclic group optionally substituted on the heterocyclic ring with one or more substituents independently selected from the group consisting of halogen, C 1-4 alkyl, C 1-4 haloalkyl, and optionally substituted heterocyclic groups; or —(CH 2 )n-Si(R 9 )(R 10 )(R 11 ) wherein R 9 , R 10 , and R 11 are each C 1-6 alkyl, and n is an integer of 0 or 1.
3. The ethynylaniline compound according to claim 2 , wherein R 8 is C 1-20 alkyl optionally substituted on the alkyl group with one or more substituents independently selected from the group consisting of C 1-4 alkoxy, hydroxy, cyano, phenyl, phenoxy, and optionally substituted heterocyclic groups; C 1-4 haloalkyl; phenyl optionally substituted on the phenyl ring with one to five substituents independently selected from the group consisting of halogen, C 1-6 alkyl, C 1-4 haloalkyl, C 1-4 alkoxy, and phenoxy; a heterocyclic group optionally substituted on the heterocyclic ring with one or more substituents independently selected from the group consisting of halogen, C 1-4 alkyl, C 1-4 haloalkyl, and optionally substituted heterocyclic groups; or —(CH 2 )n-Si(R 9 )(R 10 )(R 11 ) wherein R 9 , R 10 , and R 11 are each C 1-6 alkyl, and n is an integer of 0 or 1.
4. The ethynylaniline compound according to claim 3 , wherein R 8 is C 1-20 alkyl optionally substituted on the alkyl group with one or more substituents independently selected from the group consisting of cyano, phenyl, and optionally substituted heterocyclic groups; phenyl optionally substituted on the phenyl ring with one to five substituents independently selected from the group consisting of halogen, C 1-6 alkyl, C 1-4 haloalkyl, C 1-4 alkoxy, and phenoxy; a heterocyclic group optionally substituted on the heterocyclic ring with one or more substituents independently selected from the group consisting of halogen, C 1-4 alkyl, C 1-4 haloalkyl, and optionally substituted heterocyclic groups; or —(CH 2 )n-Si(R 9 )(R 10 )(R 11 ) wherein R 9 , R 10 , and R 11 are each C 1-6 alkyl, and n is an integer of 0 or 1.
5. The ethynylaniline compound according to claim 4 , wherein R 8 is phenyl optionally substituted on the phenyl ring with one to five substituents independently selected from the group consisting of halogen, C 1-6 alkyl, C 1-4 haloalkyl, C 1-4 alkoxy, and phenoxy; a heterocyclic group optionally substituted on the heterocyclic ring with one or more substituents independently selected from the group consisting of halogen, C 1-4 alkyl, C 1-4 haloalkyl, and optionally substituted heterocyclic groups; or —(CH 2 )n-Si(R 9 )(R 10 )(R 11 ) wherein R 9 , R 10 , and R 11 are each C 1-6 alkyl, and n is an integer of 0 or 1.
6. The ethynylaniline compound according to claim 5 , wherein R 8 is phenyl optionally substituted on the phenyl ring with one to five substituents independently selected from the group consisting of halogen, C 1-6 alkyl, C 1-4 haloalkyl, C 1-4 alkoxy, and phenoxy; or —(CH 2 )n-Si(R 9 )(R 10 )(R 11 ) wherein R 9 , R 10 , and R 11 are each C 1-6 alkyl, and n is an integer of 0 or 1.
7. The ethynylaniline compound according to claim 6 , wherein R 8 is phenyl optionally substituted on the phenyl ring with one to five substituents independently selected from the group consisting of halogen, C 1-6 alkyl, C 1-4 haloalkyl, C 1-4 alkoxy, and phenoxy.
8. The ethynylaniline compound according to claim 6 , wherein the ethynylaniline compound is represented by Formula (4) wherein R 8 is —(CH 2 )n-Si(R 9 )(R 10 )(R 11 ) wherein R 9 , R 10 , and R 11 are each C 1-6 alkyl, and n is an integer of 0 or 1.
9. The ethynylaniline compound according to claim 7 , wherein R 4 and R 6 are each fluorine, chlorine, or methyl.
10. The ethynylaniline compound according to claim 9 , wherein R 4 and R 6 are each methyl.
11. The ethynylaniline compound according to claim 8 , wherein the ethynylaniline compound is represented by Formula (4) wherein R 4 and R 6 are each fluorine, chlorine, or methyl.
12. The ethynylaniline compound according to claim 11 , wherein the ethynylaniline compound is represented by Formula (4) wherein R 4 and R 6 are each methyl.
13. The ethynylaniline compound according to claim 1 , wherein the ethynylaniline compound is represented by Formula (4) wherein R 4 and R 6 are each halogen or C 1-4 alkyl.
14. The ethynylaniline compound according to claim 13 , wherein the ethynylaniline compound is represented by Formula (4) wherein R 4 and R 6 are each fluorine, chlorine, or methyl.
15. The ethynylaniline compound according to claim 14 , wherein the ethynylaniline compound is represented by Formula (4) wherein R 4 and R 6 are each methyl.