Pesticide pyrimidinyloxy substituted phenylamidine derivatives
View Patent ↗The present invention relates to 2,5-disubstituted-4-pyrimidinyl-substituted-phenyl-amidine derivatives of formula (I) in which the substituents are as in the description, notably to 2,5-dialkyl-4-pyrimidinyl-substituted-phenyl-amidine derivatives, their process of preparation, their use as fungicide or insecticide active agents, particularly in the form of fungicide or insecticide compositions, and methods for the control of phytopathogenic fungi or damaging insects, notably of plants, using these compounds or compositions.
1. A phenyl-amidine compound of formula (I):
wherein
R 1 represents H, a substituted or non substituted C 1 -C 12 -alkyl, a substituted or non substituted C 2 -C 12 -alkenyl, a substituted or non substituted C 2 -C 12 -alkynyl, SH or a substituted or non substituted S—C 1 -C 12 -alkyl;
R 2 represents a substituted or non substituted C 1 -C 12 -alkyl;
R 3 represents a substituted or non substituted C 2 -C 12 -alkyl, substituted or non substituted C 3 -C 6 -cycloalkyl, substituted or non substituted C 2 -C 12 -alkenyl, substituted or non substituted C 2 -C 12 -alkynyl, halogeno-C 1 -C 12 -alkyl; or
R 2 and R 3 can form together a substituted or non substituted 5 to 7-membered heterocycle;
R 4 represents a substituted or non substituted C 1 -C 12 -alkyl, a halogen atom, halogeno-C 1 -C 12 -alkyl, substituted or non substituted O—C 1 -C 12 -alkyl or cyano;
R 5 represents H, a substituted or non substituted C 1 -C 12 -alkyl, a halogen atom, halogeno -C 1 -C 12 -alkyl, substituted or non substituted O—C 1 -C 12 -alkyl or cyano;
R 6 represents H, halogen, CN, substituted or non substituted phenoxy, substituted or non substituted C 1 -C 12 -alkyl, halogeno-C 1 -C 12 -alkyl, OR 7 , SR 7 , trialkyl-silyl, COOR 7 , C(R 7 )═NOR 7 ; NR 7 R 8 ;
R 7 , R 8 represent independently H, substituted or non substituted C 1 -C 12 -alkyl, aryl or R 7 and R 8 can form a substituted or non substituted, saturated or non saturated 5 to 7-membered heterocycle including one or more atoms selected in the list consisting of O, N and S;
m represents 1, 2 or 3;
as well as a salt, N-oxyde, metallic complex, metalloidic complex and/or an optically active isomer thereof.
2. A compound of formula (I) according to claim 1 wherein
R 1 represents H, C 1 -C 12 -alkyl or SH; or
R 2 represents methyl; or
R 3 represents C 2 -C 12 -alkyl, C 2 -C 12 -alkenyl, C 3 -C 6 -cycloalkyl; or
R 2 and R 3 can form together a substituted or non substituted 5- to 7-membered heterocycle; or
R 4 represents C 1 -C 12 -alkyl or a halogen atom; or
R 5 H, a substituted or non substituted C 1 -C 6 -alkyl, a halogen atom, halogeno-C 1 -C 6 -alkyl, substituted or non substituted O—C 1 -C 6 -alkyl or CN; or
R 6 which may be the same or different, represents H, halogen, CN, substituted or non substituted phenoxy, substituted or non substituted C 1 -C 12 -alkyl, halogeno-C 1 -C 12 -alkyl, OR 7 , SR 7 , trialkyl-silyl, COOR 7 , C(R 7 )═NOR 7 ; NR 7 R 8 .
3. A compound of formula (I) according to claim 1 wherein
R 1 represents C 1 -C 12 -alkyl; or
R 3 represents a non substituted C 2 -C 4 -alkyl, C 3 -C 4 -alkenyl or cyclopropyl; or
R 2 and R 3 can form together a 6-membered heterocycle; or
R 4 represents a non substituted C 1 -C 12 -alkyl or a chlorine atom; or
R 6 represents a branched C 1 -C 12 -alkyl.
4. A compound of formula (I) according to claim 1 wherein
R 1 represents methyl; or
R 3 represents ethyl, n-propyl, i-propyl, propenyl or allyl; or
R 2 and R 3 can form together a pipiridinyl or a pyrrolidinyl; or
R 4 represents methyl.
5. A compound of formula (I) according to claim 1 wherein R 2 and R 3 form together a bis-alkylated-pyrrolidinyl.
6. A compound of formula (I) according to claim 5 wherein R 2 and R 3 form together a bis-methyl-pyrrolidinyl.
7. A process for the preparation of a compound of formula (I) according to claim 1 comprising at least one of the following steps:
8. A method for controlling phytopathogenic fungi of crops, comprising applying an agronomically effective and substantially non-phytotoxic quantity of a compound according to claim 1 to soil where a plant grow or is capable of growing, to the leaves or fruit of a plant and/or to a seed of a plant.
9. A method for controlling damaging insects comprising applying a compound of formula (I) according to claim 1 to a seed, a plant and/or to a fruit of a plant and/or to soil wherein a plant is growing or wherein a plant is desired to grow.
10. A phenyl-amidine compound of formula (I):
wherein
R 1 represents H, a substituted or non substituted C 1 -C 12 -alkyl, a substituted or non substituted C 2 -C 12 -alkenyl, a substituted or non substituted C 2 -C 12 -alkynyl, SH or a substituted or non substituted S—C 1 -C 12 -alkyl;
R 2 represents a substituted or non substituted C 1 -C 12 -alkyl;
R 3 represents a substituted or non substituted C 2 -C 12 -alkyl, substituted or non substituted C 3 -C 6 -cycloalkyl, substituted or non substituted C 2 -C 12 -alkenyl, substituted or non substituted C 2 -C 12 -alkynyl, halogeno-C 1 -C 12 -alkyl; or
R 2 and R 3 can form together a substituted or non substituted 5 to 7-membered heterocycle;
R 4 represents a substituted or non substituted C 1 -C 12 -alkyl, a halogen atom, halogeno-C 1 -C 12 -alkyl, substituted or non substituted O—C 1 -C 12 -alkyl or cyano;
R 5 represents H, a substituted or non substituted C 1 -C 12 -alkyl, a halogen atom, halogeno-C 1 -C 12 -alkyl, substituted or non substituted O—C 1 -C 12 -alkyl or cyano;
R 6 represents H, halogen, CN, substituted or non substituted phenoxy, substituted or non substituted C 1 -C 12 -alkyl, halogeno-C 1 -C 12 -alkyl, OR 7 , SR 7 , trialkyl-silyl, COOR 7 , C(R 7 )═NOR 7 ; NR 7 R 8 ;
R 7 , R 8 represent independently H, substituted or non substituted C 1 -C 12 -alkyl, aryl or R 7 and R 8 can form a substituted or non substituted, saturated or non saturated 5 to 7-membered heterocycle including one or more atoms selected in the list consisting of O, N and S;
m represents 1, 2 or 3;
as well as a salt, N-oxyde, and/or an optically active isomer thereof.