US 11,155,517 B2 · 4-substituted phenylamine derivatives and their use to protect crops by fighting undesired phytopathogenic micoorganisms

Abstract

This invention related to 4-substituted phenylamine derivatives of the general formula (I), wherein R1 to R9 and A have the meanings as defined in description. The invention further relates to methods for their preparation and use of said compounds to fight undesired phytopathogenic microorganisms, and agents for said purpose, comprising said phenylamine derivatives, all according to the invention. This invention further relates to a method for fighting undesired phytopathogenic microorganisms by application of said 4-substituted phenylamine derivatives of general formula (I) to such undesired microorganisms and/or to their habitat, according to the invention.

A compound of general formula (I)

wherein,
R1 is selected from the group consisting of hydrogen, CN, C1-6-alkyl, C1-6-alkoxy, C1-6-alkylthio, C2-6-alkenyl, C2-6-alkynyl, C1-6-haloalkyl and C3-8 cycloalkyl,
R2 is selected from the group consisting of CN, OR′, C2-12-alkyl, C2-12-alkenyl, C2-12-alkynyl, C1-12-haloalkyl, C2-12-haloalkenyl, C2-12-haloalkynyl and C3-8-cycloalkyl:
one or more carbon atoms of said cyclic ring system may be replaced by heteroatoms selected from the group consisting of N, O and S(O)n;
R3 is selected from the group consisting of hydrogen, CN, OR′, C1-12-alkyl, C2-12-alkenyl, C2-12-alkynyl, C1-12-haloalkyl, C2-12-haloalkenyl, C2-12-haloalkynyl and C3-8-cycloalkyl;
wherein one or more carbon atoms of said cyclic ring system may be replaced by heteroatoms selected from the group consisting of N, O and S(O)n;
or
R1 and R2, R2 and R3 or R1 and R3 together with the atoms to which they are attached or together with further atoms selected from the group consisting of C, N, O, S and optionally including 1 to 3 ring members selected from the group consisting of C(═O), C(═S), S(O)m and SiR′2 may form a four to seven membered non-aromatic ring, which for its part may be substituted by one or more X, R′, OR′, SR′, NR′2, SiR′3, CN and CONR′2;
or
each group of R1, R2 and R3 may optionally be substituted by one or more groups selected from the group consisting of X, R′, OR′, SR′, NR′2, SiR′3, COOR′, CN and CONR′2;
R4 and R5, are independently selected from the group consisting of hydrogen, X, CN, SCN, SF5, S(O)nR″, SiR′3, OR″, NR′R″, (C═O)—R″, CR′═NR″, C1-12-alkyl, C2-12-alkenyl, C2-12-alkynyl, C1-12-haloalkyl, C2-12-haloalkenyl, C2-12-haloalkynyl, C1-12-haloalkoxy, C1-12-haloalkylthio, C3-8-cycloalkyl, C3-8-cycloalkyloxy, C3-8-cycloalkylthio, C5-18-aryl, C7-19-aralkyl and C7-19-alkaryl;
wherein one or more carbon atoms of said cyclic ring system may be replaced by heteroatoms selected from the group consisting of N, O and S(O)n;
R6 and R7 are independently selected from the group consisting of hydrogen, X, CN, S(O)nR″, OR″, NR′R″, C1-6-alkyl, C2-6-alkenyl, C2-6-alkynyl, C1-6-haloalkyl, C2-6-haloalkenyl, C1-6-haloalkoxy, C1-6-haloalkylthio, C3-8-cycloalkyl, C3-8-cycloalkoxy, C3-6-cycloalkylthio;
or
R4 and R7 or R5 and R6 together with the atom to which they are attached or together with further atoms selected from the group consisting of C, N, O, S and optionally including 1 to 3 ring members selected from the group consisting of C(═O), C(═S), S(O)m and SiR′2 may form a four to seven membered ring, which for its part may be substituted by one or more X, R′, OR′, SR′, NR′2, SiR′3, COOR′, CN and CONR′2;
or
each group of R4, R5, R6 and R7 may optionally be substituted by one or more groups selected from the group consisting of X, R′, OR′, SR′, NR′2, SiR′3, COOR′, CN, and CONR′2;
R8 and R9 are independently selected from the group consisting of hydrogen, X, CN, OS(O)nR″, SiR′3, OSiR′3, (C═O)—R″, C1-6-alkyl, C2-6-alkenyl, C2-6-alkynyl, C1-6-alkoxy, C2-6-alkenyloxy, C2-6-alkynyloxy, C1-6 haloalkyl, C2-6-haloalkenyl, C2-6-haloalkynyl, C1-6-haloalkoxy, C3-8-cycloalkyl, and C3-8-cycloalkyloxy, wherein one or more carbon atoms of said cyclic ring system may be replaced by heteroatoms selected from the group consisting of N, O and S(O)n;
or
R6 and R9 together with the atom to which they are attached or together with further atoms selected from the group consisting of C, N, O, S and optionally including 1 to 3 ring members selected from the group consisting of C(═O), C(═S), S(O)m and SiR′2 may form a three to seven membered ring, which for its part may be substituted by one or more X, R′, OR′, SR′, NR′2, SiR′3, COOR′, CN and CONR′2;
or
R8 and R9 together with the atom to which they are attached may form a group of ═C(R′R″), ═S or ═NR″;
A is selected from the group consisting of fused or non-fused C6-18-aryl and C5-18-heteroaryl, wherein one or more carbon atoms are replaced by heteroatoms selected from N, O, S and optionally including 1 to 3 ring members selected from the group consisting of C(═O), C(═S), S(O)m, SiR′2 and further optionally substituted by one or more groups of R10;
with the proviso that heteroaryl does not represent thiazolyl or thiadiazolyl;
phenyl10 is selected from the group consisting of hydrogen, X, CN, SCN, SF5, R″, OR″, NO2, NR″2, SiR′3, (C═O)—R″, S(O)nR″, OS(O)nR″, NR′S(O)nR″, OSiR′3, C1-8-alkyl-S(O)nR″, C1-8-alkyl-(C═O)—R″, CR′═NR″, S(O)nC5-18-aryl, S(O)nC7-19-aralkyl, S(O)nC7-19-alkaryl, C1-12-alkyl, C2-12-alkenyl, C2-12-alkynyl, C1-12-haloalkyl, C2-12-haloalkenyl, C2-12-haloalkynyl, C1-12-alkoxy, C1-12-alkylthio, C1-12-holoalkoxy, C1-12-haloalkylthio, C3-12-cycloalkyl, C4-8-cycloalkenyl, C5-8-cycloalkynyl, C3-8-cycloalkyloxy, C3-8-cycloalkylthio, C7-19-aralkyl, C7-19-alkaryl, bicyclic C5-12-alkyl and bicyclc C7-12-alkenyl;
one or more carbon atoms of said cyclic ring system may be replaced by heteroatoms selected from the group consisting of N, O, and S(O)n:
or
two R10 together with the atom to which they are attached or together with further atoms selected from the group consisting of C, N, O, S and optionally including 1 to 3 ring members selected from the group consisting of C(═O), C(═S), S(O)m and SiR′3 may form a four to ten membered ring, which for its part may be substituted by one or more X, R′, OR′, SR′, NR′2, SiR′3, COOR′, CN and CONR′2;
each group of R8 and R9 may optionally be substituted by one or more groups selected from the group consisting of X, R′, OR′, SR′, NR′2, SiR′3, COOR′, CN, and CONR′2;
R10 may optionally be substituted by one or more groups selected from the group consisting of X, R′, SR′, NR′2, SiR′3, COOR′, CN, and CONR′2;
X represents halogen;
R′ is selected from the groups consisting of hydrogen, straight chain or branched chain C1-6-alkyl and cyclic C3-8-alkyl;
wherein each group of R′ is optionally substituted by one or more X;
R″ is selected from the groups consisting of hydrogen, NR′2, OR′, straight chain or branched chain C1-6-alkyl, C1-6-haloalkyl and cyclic C3-8-alkyl;
wherein each group of R″ is optionally substituted by one or more groups selected from the group consisting of X, R′, OR′, SR′, NR′2, SiR′3, COOR′, CN, and CONR′2, or R″ is phenyl which is optionally substituted by one or more R′;
m and n represent integers, n=0, 1 or 2;
and m=1 or 2;
and agronomically acceptable salts, metallic complexes, stereo-isomers, diastereoisomers, enantiomers, tautomers, or N-oxides thereof.

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4-substituted phenylamine derivatives and their use to protect crops by fighting undesired phytopathogenic micoorganisms

Life of this patent

4-substituted phenylamine derivatives and their use to protect crops by fighting undesired phytopathogenic micoorganisms

Life of this patent

Abstract

Claims18