3-substituted phenylamidine compounds, preparation and use thereof
AssigneePi Industries Ltd.
InventorsMaruti Naik, Vishal A. Mahajan, S. Sivakumar, Kishor Singh Rathod, Sachin Nagnath Gumme, Santosh Shridhar Autkar, Ruchi Garg, Hagalavadi M Venkatesha, Alexander G. M. Klausener
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Abstract
The present invention disclosed 3-substituted phenylamidine compounds of general formula (I), wherein R1, R2, R3, R4, R4a, R4b, A and E have the same meanings as defined in description. The present invention further discloses methods for their preparation and use of the compounds of general formula (I) as a crop protection agent.
Claims21
A compound of formula (I),
- wherein,
- R1 is selected from the group consisting of C1-C12-alkyl, C2-C12-alkenyl, C2-C12-alkynyl, C1-C12-haloalkyl, C1-C12-alkoxy, C3-C8-cycloalkyl and C4-C8-cycloalkylalkyl;
- R2 is selected from C2-C12-alkyl;
- or
- R1 and R2 together with the atoms to which they are attached or together with further atoms selected from the group consisting of C, N, O, S(O)m and optionally including 1 to 3 ring members selected from the group consisting of C(═O) or C(═S) may form a three to seven membered non aromatic ring, which for its part may be substituted by one or more groups selected from the group consisting of X, CN, R′, OR′, SR′, N(R′)2, COOR′ and CON(R′)2;
- R3 is selected from the group consisting of X, cyano, C1-C12-alkyl, C2-C12-alkenyl, C2-C12-alkynyl, C1-C12-haloalkyl, N(R′R′″), OR″, S(O)nR′″, (C═O)—R″ and C3-C8-cycloalkyl;
- R4 is selected from the group consisting of X, cyano, C1-C12-alkyl, C2-C12-alkenyl, C2-C12-alkynyl, C1-C12-haloalkyl, N(R′R′″), OR″, S(O)nR′″, (C═O)—R″, C3-C8-cycloalkyl and C7-C12-aralkyl;
- R4a and R4b are independently selected from the group consisting of hydrogen, X, and C1-C4-alkyl;
- A represents —{[C(R6R7)]0-2—(B)0-1}— wherein B represents NR5 or CR6R7;
- or A represents —{[B—C(R6R7)]—C(═Y)}— wherein B represent O, S, NR5 or CR6R7;
- and Y represents O or S;
- R5 is selected from the group consisting of hydrogen, and C1-C8-alkyl;
- R6 and R7 are independently selected from the group consisting of hydrogen, X, cyano, C1-C8-alkyl, and C1-C8-haloalkyl;
- R6 and R7 together with the atom to which they are attached or together with further atoms selected from the group consisting of C, N, O, S(O)m and optionally including 1 to 3 ring members selected from the group consisting of C(═O) or C(═S) may form a three to six membered ring, which for its part may be substituted by one or more groups selected from the group consisting of X, CN, R′, OR′, SR′, N(R′)2, COOR′ and CON(R′)2;
- ring E is selected from the group consisting of fused or non-fused C3-C18-carbocyclyl and C3-C18-heterocyclyl, which may optionally be substituted by one or more groups of R8;
- R8 is selected from the group consisting of hydrogen, X, cyano, nitro, C1-C12-alkyl, C2-C12-alkenyl, C2-C12-alkynyl, C1-C12-haloalkyl, C2-C12-haloalkenyl, C2-C12-haloalkynyl, C3-C8-cycloalkyl, C4-C8-cycloalkenyl, C4-C8-cycloalkynyl, C7-C19-aralkyl, C5-C12-bicycloalkyl, C6-C10-aryl, C3-C6-heterocyclyl, SCN, SF5, N(R′R′″), OR″, S(O)nR′″, (C═O)—R′″, C1-C8-alkyl-S(O)nR″, C1-C8-alkyl-(C═O)—R″, CR′═NR″, —S(R9)═N(R10), —S(R9)(O)═N(R10), S(R9)2═N—, S(R9)2(O)═N— and S(R9)2(O)═N—C(R6aR7a)—;
- wherein one or more carbon atoms in cyclic ring may be replaced by heteroatoms selected from the group consisting of N, O, S(O)m and optionally including 1 to 3 ring members selected from the group consisting of C(═O) and C(═S);
- R6a and R7a are independently selected from the group consisting of hydrogen, X, cyano, C1-C8-alkyl, C2-C8-alkenyl, C2-C8-alkynyl, C1-C8-haloalkyl, C2-C8-haloalkenyl, (NR″)2, OR″, S(O)nR′″, (C═O)—R″ and C3-C8-cycloalkyl;
- or
- R6a and R7a together with the atom to which they are attached or together with further atoms selected from the group consisting of C, N, O, S(O)m and optionally including 1 to 3 ring members selected from the group consisting of C(═O) and C(═S), may form a three to six membered ring, which for its part may be substituted by one or more group selected from the group consisting of X, CN, R′, OR′, SR′, N(R′)2, COOR′ and CON(R′)2;
- or
- R6a and R7a together with the atom to which they are attached may form a group of ═O or ═S;
- R9 is independently selected from the group consisting of C1-C8-alkyl and C3-C8-cycloalkyl;
- R10 is selected from the group consisting of hydrogen, cyano, C1-C8-alkyl, C2-C8-alkenyl, C2-C8-alkynyl, (C═O)—R″, S(O)nR′″ and C3-C8-cycloalkyl;
- or
- R9 and 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(O)m and optionally including 1 to 3 ring members selected from the group consisting of C(═O) or C(═S) may form a three to seven membered ring, which for its part may be substituted by one or more groups selected from the group consisting of X, CN, R′, OR′, SR′, N(R′)2, COOR′ and CON(R′)2;
- or
- R8 and R9 or 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(O)m and optionally including 1 to 3 ring members selected from the group consisting of C(═O) or C(═S) may form a three to seven membered ring, which for its part may be substituted by one or more groups selected from the group consisting of X, CN, R′, OR′, SR′, N(R′)2, COOR′ and CON(R′)2;
- R5 or R6 or R7 and R8 or two R8 together with the atoms to which they are attached or together with further atoms selected from the group consisting of C, N, O, S(O)m and optionally including 1 to 3 ring members selected from the group consisting of C(═O) or C(═S), may form a three to ten membered ring, which for its part may be substituted by one or more groups selected from the group consisting of X, CN, R′, OR′, SR′, N(R′)2, COOR′ and CON(R′)2;
- X represents halogen;
- R′ is selected from the group consisting of hydrogen, C1-C8-alkyl and C3-C8-cycloalkyl;
- wherein alkyl and cycloalkyl group may be optionally substituted by one or more X;
- R″ is selected from the group consisting of hydrogen, C1-C8-alkyl, C1-C8-haloalkyl, C3-C8-cycloalkyl, N(R′)2, and OR′;
- R′″ is selected from R″;
- n represents integer 0, 1 or 2;
- m represents an integer 0, 1 or 2;
- or agriculturally acceptable salts, stereo-isomers, polymorphs, or N-oxides thereof.
A compound of formula (A),
- wherein,
- Z represent OH, NH2, SH, X, or leaving group;
- R1 is selected from the group consisting of C1-C12-alkyl, C2-C12-alkenyl, C2-C12-alkynyl, C1-C12-haloalkyl, and C3-C8-cycloalkyl;
- R2 is selected from C2-C12-alkyl;
- R3 is selected from the group consisting of X, cyano, C1-C12-alkyl, C2-C12-alkenyl, C2-C12-alkynyl, C1-C12-haloalkyl, N(R′R′″), OR″, S(O)nR′″, (C═O)—R″ and C3-C8-cycloalkyl;
- R4 is selected from the group consisting of X, cyano, C1-C12-alkyl, C2-C12-alkenyl, C2-C12-alkynyl, C1-C12-haloalkyl, N(R′R′″), OR″, S(O)nR′″, (C═O)—R″, C3-C8-cycloalkyl and C7-C12-aralkyl.
A compound selected from the group consisting of 2-chloro-5-methyl-N1-(p-tolyl)benzene-1,3-diamine, 2,5-dimethyl-3-(4-methylbenzyl)aniline, 3-(3-chlorobenzyl)-2,5-dimethylaniline, 2,5-dimethyl-3-(2-methylbenzyl)aniline, 3-(3-fluorobenzyl)-2,5-dimethylaniline, N1-(2-fluorophenyl)-2,5-dimethylbenzene-1,3-diamine, N1-(2-fluorophenyl)-N1,2,5-trimethylbenzene-1,3-diamine, 5-fluoro-2-methyl-N1-phenylbenzene-1,3-diamine, 2-chloro-5-methyl-N1-phenylbenzene-1,3-diamine, 2-chloro-N1,5-dimethyl-N1-phenylbenzene-1,3-diamine, 5-fluoro-N1,2-dimethyl-N1-phenylbenzene-1,3-diamine, 2-chloro-5-methyl-3-(2-methylbenzyl)aniline, 2-chloro-3-(2-chlorobenzyl)-5-methylaniline, 2-chloro-3-(2-fluorobenzyl)-5-methylaniline, 5-fluoro-2-methyl-N1-(o-tolyl)benzene-1,3-diamine, 5-fluoro-2-methyl-N1-(4-((trifluoromethyl)thio)phenyl)benzene-1,3-diamine, 2-chloro-5-methyl-3-(3-methylbenzyl)aniline, 2-chloro-5-methyl-3-(4-methylbenzyl)aniline, 5-fluoro-N1-(2-fluorophenyl)-2-methylbenzene-1,3-diamine, N1-(4-(tert-butyl)phenyl)-5-fluoro-2-methylbenzene-1,3-diamine, 2-chloro-5-methyl-3-(2-(trifluoromethyl)benzyl)aniline, 2-chloro-3-(3-fluorobenzyl)-5-methylaniline, 2-chloro-N1-(2-fluorophenyl)-5-methylbenzene-1,3-diamine, 2-chloro-5-methyl-N1-(o-tolyl)benzene-1,3-diamine, N1-(4-(tert-butyl)phenyl)-2-chloro-5-methylbenzene-1,3-diamine, 2-chloro-5-methyl-N1-(4-((trifluoromethyl)thio)phenyl)benzene-1,3-diamine, 2-chloro-3-(3-chlorobenzyl)-5-methylaniline, 2-chloro-3-(3-methoxybenzyl)-5-methylaniline, 5-fluoro-N1-(3-fluorophenyl)-2-methylbenzene-1,3-diamine, 5-fluoro-N1-(3-methoxyphenyl)-2-methylbenzene-1,3-diamine, 5-fluoro-2-methyl-N1-(m-tolyl)benzene-1,3-diamine, 5-fluoro-N1-(3-fluorophenyl)-N1,2-dimethylbenzene-1,3-diamine, N1-(3-chlorophenyl)-5-fluoro-N1,2-dimethylbenzene-1,3-diamine, 2-chloro-N1-(3-chlorophenyl)-5-methylbenzene-1,3-diamine, 2-chloro-N1-(3-fluorophenyl)-5-methylbenzene-1,3-diamine, 2-chloro-5-methyl-N1-(m-tolyl)benzene-1,3-diamine, N1-(3-chlorophenyl)-5-fluoro-2-methylbenzene-1,3-diamine, 5-fluoro-N1,2-dimethyl-N1-(m-tolyl)benzene-1,3-diamine, 5-fluoro-N1-(3-methoxyphenyl)-N1,2-dimethylbenzene-1,3-diamine, 2-chloro-N1-(3-fluorophenyl)-N1,5-dimethylbenzene-1,3-diamine, 2-chloro-N1-(3-chlorophenyl)-N1,5-dimethylbenzene-1,3-diamine, 2-chloro-N1-(3-methoxyphenyl)-5-methylbenzene-1,3-diamine, 2-chloro-N1,5-dimethyl-N1-(m-tolyl)benzene-1,3-diamine, 2-chloro-3-(4-fluorobenzyl)-5-methylaniline, 3-(2-bromobenzyl)-2-chloro-5-methylaniline, 4-(3-amino-2-chloro-5-methylbenzyl)benzonitrile, 2-(3-amino-2-chloro-5-methylbenzyl)benzonitrile, 3-(3-amino-2-chloro-5-methylbenzyl)benzonitrile, 2-chloro-N1-(3-methoxyphenyl)-N1,5-dimethylbenzene-1,3-diamine, 2-chloro-5-methyl-3-(2-(trifluoromethoxy)benzyl)aniline, 2-chloro-5-methyl-3-(4-(trifluoromethyl)benzyl)aniline, 2-chloro-5-methyl-3-(4-(trifluoromethoxy)benzyl)aniline, 2-chloro-5-methyl-3-(3-(trifluoromethyl)benzyl)aniline, 2-chloro-3-(3-chloro-4-fluorobenzyl)-5-methylaniline, 2-chloro-3-(3,5-dimethylbenzyl)-5-methylaniline, 2-chloro-3-(3-chloro-2-fluorobenzyl)-5-methylaniline, 2-chloro-3-(5-fluoro-2-methylbenzyl)-5-methylaniline, 2-chloro-N1-(3-isopropylphenyl)-5-methylbenzene-1,3-diamine, 2-chloro-N1-(4-chlorophenyl)-5-methylbenzene-1,3-diamine, 2-chloro-N1-(4-fluorophenyl)-5-methylbenzene-1,3-diamine, 2-chloro-N1-(4-methoxyphenyl)-5-methylbenzene-1,3-diamine, 2-chloro-N1-(4-chlorophenyl)-N1,5-dimethylbenzene-1,3-diamine, 2-chloro-N1-(3-isopropylphenyl)-N1,5-dimethylbenzene-1,3-diamine, 2-chloro-N1-(4-methoxyphenyl)-N1,5-dimethylbenzene-1,3-diamine, 2-chloro-3-(4-fluoro-2-methylbenzyl)-5-methylaniline, 2-chloro-5-methyl-3-(pyridin-3-ylmethyl)aniline, 2-chloro-3-(3,4-difluorobenzyl)-5-methylaniline, 2-chloro-3-(4-fluoro-3-methylbenzyl)-5-methylaniline, 2-chloro-N1-(4-fluorophenyl)-N1,5-dimethylbenzene-1,3-diamine, 3-benzyl-2-chloro-5-methylaniline, 2-chloro-3-(3,5-difluoro-4-methoxybenzyl)-5-methylaniline, 2-chloro-N1-(3,4-difluorophenyl)-5-methylbenzene-1,3-diamine, N1-(3,4-difluorophenyl)-5-fluoro-2-methylbenzene-1,3-diamine, 2-chloro-N1-(3,5-difluorophenyl)-N1,5-dimethylbenzene-1,3-diamine, 2-chloro-N1-(2,4-difluorophenyl)-5-methylbenzene-1,3-diamine, N1-(2,4-difluorophenyl)-5-fluoro-2-methylbenzene-1,3-diamine, N1-(3,5-difluorophenyl)-5-fluoro-2-methylbenzene-1,3-diamine, 2-chloro-N1-(3,5-difluorophenyl)-5-methylbenzene-1,3-diamine, 3-benzyl-5-chloro-2-methylaniline, N1-(2,4-difluorophenyl)-5-fluoro-N1,2-dimethylbenzene-1,3-diamine, 2-chloro-N1-(3,4-difluorophenyl)-N1,5-dimethylbenzene-1,3-diamine, 2-chloro-N1-(2,4-difluorophenyl)-N1,5-dimethylbenzene-1,3-diamine, N1-(3,4-difluorophenyl)-5-fluoro-N1,2-dimethylbenzene-1,3-diamine, N1-(3,5-difluorophenyl)-5-fluoro-N1,2-dimethylbenzene-1,3-diamine, 2-chloro-5-methyl-N1-(pyridin-2-yl)benzene-1,3-diamine, 2-chloro-5-methyl-N1-(3-methylpyridin-2-yl)benzene-1,3-diamine, 5-chloro-3-(4-fluoro-3,5-dimethylbenzyl)-2-methylaniline, 5-chloro-2-methyl-3-(2-methylbenzyl)aniline, 5-chloro-3-(2-chlorobenzyl)-2-methylaniline, 3-(2-bromobenzyl)-5-chloro-2-methylaniline, 2-chloro-3-(2,6-difluorobenzyl)-5-methylaniline, 2-chloro-3-(2-chloro-6-fluorobenzyl)-5-methylaniline, 3-(4-bromobenzyl)-2-chloro-5-methylaniline, 5-chloro-2-methyl-3-(3-methylbenzyl)aniline, 5-fluoro-2-methyl-N1-(pyridin-2-yl)benzene-1,3-diamine, N1-(3-chloro-5-fluorophenyl)-5-fluoro-2-methylbenzene-1,3-diamine, 2-chloro-N1-(3-chloro-5-fluorophenyl)-5-methylbenzene-1,3-diamine, N1-(5-chloro-2-methylphenyl)-5-fluoro-N1,2-dimethylbenzene-1,3-diamine, 2-chloro-N1-(3-chloro-5-fluorophenyl)-N1,5-dimethylbenzene-1,3-diamine, 2-chloro-N1-(5-chloro-2-methylphenyl)-5-methylbenzene-1,3-diamine, 5-chloro-3-(3-chlorobenzyl)-2-methylaniline, 5-chloro-3-(3-fluorobenzyl)-2-methylaniline, 5-chloro-3-(2-fluorobenzyl)-2-methylaniline, 2-(3-amino-5-chloro-2-methylbenzyl)benzonitrile, 5-chloro-2-methyl-3-(4-methylbenzyl)aniline, N1-(3-chloro-5-fluorophenyl)-5-fluoro-N1,2-dimethylbenzene-1,3-diamine, 2-chloro-N1,5-dimethyl-N1-(pyridin-2-yl)benzene-1,3-diamine, 2-chloro-N1,5-dimethyl-N1-(3-methylpyridin-2-yl)benzene-1,3-diamine, 5-fluoro-N1,2-dimethyl-N1-(pyridin-2-yl)benzene-1,3-diamine, 2-chloro-N1-(5-chloro-2-methylphenyl)-N1,5-dimethylbenzene-1,3-diamine, 2-chloro-N1-(3-fluoro-5-methylphenyl)-5-methylbenzene-1,3-diamine, 2-chloro-N1-(5-chloro-3-methylpyridin-2-yl)-5-methylbenzene-1,3-diamine, N1-(2-chloro-5-methylphenyl)-5-fluoro-2-methylbenzene-1,3-diamine, 5-fluoro-N1-(3-fluoro-5-methylphenyl)-2-methylbenzene-1,3-diamine, 2-chloro-N1-(2-chloro-5-methylphenyl)-5-methylbenzene-1,3-diamine, N1-(5-chloro-2-methylphenyl)-5-fluoro-2-methylbenzene-1,3-diamine, N1-(2-chloro-5-methylphenyl)-5-fluoro-N1,2-dimethylbenzene-1,3-diamine, 2-chloro-N1-(5-chloro-3-methylpyridin-2-yl)-N1,5-dimethylbenzene-1,3-diamine, 5-fluoro-N1-(3-fluoro-5-methylphenyl)-N1,2-dimethylbenzene-1,3-diamine, 2-chloro-N1-(2-chloro-5-methylphenyl)-N1,5-dimethylbenzene-1,3-diamine, 5-fluoro-N1-(2-fluoro-6-methylphenyl)-2-methylbenzene-1,3-diamine, 5-fluoro-N1-(2-fluoro-3-methylphenyl)-2-methylbenzene-1,3-diamine, 2-chloro-N1-(2-fluoro-3-methylphenyl)-5-methylbenzene-1,3-diamine, 5-chloro-3-(4-fluorobenzyl)-2-methylaniline, 3-(4-bromobenzyl)-5-chloro-2-methylaniline, 5-chloro-3-(4-chlorobenzyl)-2-methylaniline, 5-chloro-2-methyl-3-(3-(trifluoromethyl)benzyl)aniline, 5-chloro-3-(4-fluoro-3-methylbenzyl)-2-methylaniline, 5-chloro-3-(3,4-difluorobenzyl)-2-methylaniline, 5-chloro-3-(3-chloro-4-fluorobenzyl)-2-methylaniline, 5-chloro-3-(4-chloro-3-fluorobenzyl)-2-methylaniline, 5-fluoro-2-methyl-N1-(3-(trifluoromethyl)pyridin-2-yl)benzene-1,3-diamine, 2-chloro-N1-(2-fluoro-6-methylphenyl)-5-methylbenzene-1,3-diamine, 2-chloro-N1-(4-chloro-2-fluorophenyl)-5-methylbenzene-1,3-diamine, 2-chloro-5-methyl-N1-(3-(trifluoromethyl)pyridin-2-yl)benzene-1,3-diamine, N1-(4-chloro-2-fluorophenyl)-5-fluoro-2-methylbenzene-1,3-diamine, 2-chloro-N1-(3-chloro-5-(trifluoromethyl)phenyl)-5-methylbenzene-1,3-diamine, 2-chloro-N1-(2-fluoro-6-methylphenyl)-N1,5-dimethylbenzene-1,3-diamine, 2-chloro-N1-(2-fluoro-3-methylphenyl)-N1,5-dimethylbenzene-1,3-diamine, N1-(4-chloro-2-fluorophenyl)-5-fluoro-N1,2-dimethylbenzene-1,3-diamine, 5-fluoro-3-(2-fluorobenzyl)-2-methylaniline, 3-(2-chlorobenzyl)-5-fluoro-2-methylaniline, 5-fluoro-2-methyl-3-(2-(trifluoromethyl)benzyl)aniline, 3-(3-chlorobenzyl)-5-fluoro-2-methylaniline, 5-fluoro-N1-(2-fluoro-6-methylphenyl)-N1,2-dimethylbenzene-1,3-diamine, 5-fluoro-2-methyl-3-(3-methylbenzyl)aniline, 5-fluoro-3-(3-fluorobenzyl)-2-methylaniline, 5-fluoro-2-methyl-3-(2-methylbenzyl)aniline, 3-benzyl-5-fluoro-2-methylaniline, 2-chloro-3-(4-methoxybenzyl)-5-methylaniline, 3-(2-bromobenzyl)-5-fluoro-2-methylaniline, 5-fluoro-N1-(2-fluoro-3-methylphenyl)-N1,2-dimethylbenzene-1,3-diamine, 5-fluoro-N1,2-dimethyl-N1-(3-(trifluoromethyl)pyridin-2-yl)benzene-1,3-diamine, 5-chloro-2-methyl-N1-(m-tolyl)benzene-1,3-diamine, 5-chloro-2-methyl-N1-phenylbenzene-1,3-diamine, 2-chloro-N1-(4-chloro-2-fluorophenyl)-N1,5-dimethylbenzene-1,3-diamine, 2-chloro-N1,5-dimethyl-N1-(3-(trifluoromethyl)pyridin-2-yl)benzene-1,3-diamine, 2-chloro-N1-(3-chloro-5-(trifluoromethyl)phenyl)-N1,5-dimethylbenzene-1,3-diamine, 5-chloro-N1,2-dimethyl-N1-phenylbenzene-1,3-diamine, 5-chloro-N1,2-dimethyl-N1-(m-tolyl)benzene-1,3-diamine, N1-(3-chloro-5-(trifluoromethyl)phenyl)-5-fluoro-2-methylbenzene-1,3-diamine, 5-chloro-N1-(4-methoxyphenyl)-2-methylbenzene-1,3-diamine, 5-chloro-N1-(3-chlorophenyl)-2-methylbenzene-1,3-diamine, N1-(3-bromophenyl)-5-chloro-2-methylbenzene-1,3-diamine, 5-chloro-N1-(2-fluorophenyl)-2-methylbenzene-1,3-diamine, 5-chloro-N1-(3-fluorophenyl)-2-methylbenzene-1,3-diamine, 5-chloro-N1-(4-methoxyphenyl)-N1,2-dimethylbenzene-1,3-diamine, 2-(3-amino-5-fluoro-2-methylbenzyl)benzonitrile, 2-chloro-N1-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-5-methylbenzene-1,3-diamine, 5-fluoro-2-methyl-3-(2-(trifluoromethoxy)benzyl)aniline, 5-fluoro-2-methyl-3-(4-methylbenzyl)aniline, 3-(4-chlorobenzyl)-5-fluoro-2-methylaniline, 5-fluoro-2-methyl-3-(3-(trifluoromethoxy)benzyl)aniline, 3-(3-amino-5-fluoro-2-methylbenzyl)benzonitrile, 3-(4-bromobenzyl)-5-fluoro-2-methylaniline, 5-fluoro-2-methyl-3-(4-(trifluoromethoxy)benzyl)aniline, 2-chloro-N1-(2-(difluoromethoxy)phenyl)-5-methylbenzene-1,3-diamine, 5-chloro-N1-(2-fluorophenyl)-N1,2-dimethylbenzene-1,3-diamine, 5-chloro-N1-(3-fluorophenyl)-N1,2-dimethylbenzene-1,3-diamine, 5-chloro-N1-(3-chlorophenyl)-N1,2-dimethylbenzene-1,3-diamine, 2-chloro-5-methyl-N1-(2-(trifluoromethyl)benzyl)benzene-1,3-diamine, 5-fluoro-N1-(4-fluoro-3-methylbenzyl)-2-methylbenzene-1,3-diamine, 5-chloro-N1-(3-chlorobenzyl)-2-methylbenzene-1,3-diamine, 2-chloro-N1-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-N1,5-dimethylbenzene-1,3-diamine, 5-chloro-2-methyl-N1-(o-tolyl)benzene-1,3-diamine, 2-chloro-5-methyl-N1-(pyrimidin-2-yl)benzene-1,3-diamine, 5-fluoro-2-methyl-N1-(pyrimidin-2-yl)benzene-1,3-diamine, 5-fluoro-2-methyl-3-(4-(trifluoromethyl)benzyl)aniline, 2-bromo-3-(3-fluorobenzyl)-5-methylaniline, 3-(3-fluorobenzyl)-5-methyl-2-(methylthio)aniline, 5-chloro-N1,2-dimethyl-N1-(o-tolyl)benzene-1,3-diamine, 2-chloro-N1,5-dimethyl-N1-(pyrimidin-2-yl)benzene-1,3-diamine, 5-fluoro-2-methyl-N1-(pyrazin-2-yl)benzene-1,3-diamine, 2-chloro-5-methyl-N1-(pyrazin-2-yl)benzene-1,3-diamine, 2-chloro-5-methyl-N1-(1-(pyrazin-2-yl)propan-2-yl)benzene-1,3-diamine, 2-chloro-5-methyl-N1-((5-methylpyrazin-2-yl)methyl)benzene-1,3-diamine, 5-fluoro-2-methyl-N1-(1-(pyrazin-2-yl)propan-2-yl)benzene-1,3-diamine, 5-fluoro-2-methyl-N1-((5-methylpyrazin-2-yl)methyl)benzene-1,3-diamine, 5-fluoro-N1,2-dimethyl-N1-(pyrazin-2-yl)benzene-1,3-diamine, 5-fluoro-N1,2-dimethyl-N1-(pyrimidin-2-yl)benzene-1,3-diamine, 5-fluoro-2-methyl-3-(3-(trifluoromethyl)benzyl)aniline, 4-(3-amino-5-fluoro-2-methylbenzyl)benzonitrile, 5-fluoro-3-(4-fluoro-3-methylbenzyl)-2-methylaniline, 5-fluoro-3-(4-fluorobenzyl)-2-methylaniline, 3-(3-bromobenzyl)-5-fluoro-2-methylaniline, 3-(4-chloro-3-fluorobenzyl)-5-fluoro-2-methylaniline, 3-benzyl-2,5-dimethylaniline, 2,5-dimethyl-3-(3-methylbenzyl)aniline, 2-bromo-5-methyl-3-(2-methylbenzyl)aniline, 2-chloro-N1,5-dimethyl-N1-(pyrazin-2-yl)benzene-1,3-diamine, 5-chloro-2-methyl-N1-(pyrazin-2-yl)benzene-1,3-diamine, 5-chloro-2-methyl-N1-(pyrimidin-2-yl)benzene-1,3-diamine, 5-chloro-N1,2-dimethyl-N1-(pyrazin-2-yl)benzene-1,3-diamine, 5-chloro-N1,2-dimethyl-N1-(pyrimidin-2-yl)benzene-1,3-diamine, 3-(2-bromo-4-fluorobenzyl)-2-chloro-5-methylaniline, 3-(4-bromo-3-methylbenzyl)-2-chloro-5-methylaniline, 3-(4-bromo-2-fluorobenzyl)-2-chloro-5-methylaniline, 2-chloro-3-(4-fluoro-3-(trifluoromethyl)benzyl)-5-methylaniline, 3-(2-fluorobenzyl)-2,5-dimethylaniline, 3-(2-chlorobenzyl)-2,5-dimethylaniline, 3-(2-bromobenzyl)-2,5-dimethylaniline, 3-(4-fluorobenzyl)-2,5-dimethylaniline, 3-(4-bromobenzyl)-2,5-dimethylaniline, 3-(4-chlorobenzyl)-2,5-dimethylaniline, N1-(benzo[d]thiazol-6-yl)-5-fluoro-2-methylbenzene-1,3-diamine, 2-chloro-N1-(6-ethylpyridin-2-yl)-5-methylbenzene-1,3-diamine, N1-(6-ethylpyridin-2-yl)-5-fluoro-2-methylbenzene-1,3-diamine, N1-(benzo[d]thiazol-6-yl)-2-chloro-5-methylbenzene-1,3-diamine, 3-(2-chloro-5-fluorobenzyl)-5-fluoro-2-methylaniline, 3-(2-bromo-4-fluorobenzyl)-5-fluoro-2-methylaniline, 5-fluoro-3-(5-fluoro-2-methylbenzyl)-2-methylaniline, 3-(4-bromo-3-methylbenzyl)-5-fluoro-2-methylaniline, 3-(2-bromo-5-fluorobenzyl)-5-fluoro-2-methylaniline, 5-fluoro-3-(4-fluoro-3-(trifluoromethyl)benzyl)-2-methylaniline, 5-fluoro-3-(3-fluoro-5-methylbenzyl)-2-methylaniline, 3-(4-bromo-2-fluorobenzyl)-5-fluoro-2-methylaniline, 5-fluoro-3-(3-fluoro-5-methoxybenzyl)-2-methylaniline, N1-(benzo[d]thiazol-6-yl)-5-fluoro-N1,2-dimethylbenzene-1,3-diamine, N1-(6-ethylpyridin-2-yl)-5-fluoro-N1,2-dimethylbenzene-1,3-diamine, N1-(benzo[d]thiazol-6-yl)-2-chloro-N1,5-dimethylbenzene-1,3-diamine, 5-fluoro-2-methyl-3-(4-(methylthio)benzyl)aniline, N1-(benzo[d]thiazol-6-yl)-5-chloro-2-methylbenzene-1,3-diamine, 5-chloro-N1-(6-ethylpyridin-2-yl)-2-methylbenzene-1,3-diamine, 5-chloro-2-methyl-3-(2-(trifluoromethyl)benzyl)aniline, 3-(3-bromobenzyl)-5-chloro-2-methylaniline, 4-(3-amino-5-chloro-2-methylbenzyl)benzonitrile, 5-chloro-2-methyl-3-(2-(trifluoromethoxy)benzyl)aniline, 5-chloro-2-methyl-3-(pyridin-3-ylmethyl)aniline, 5-chloro-2-methyl-3-(4-(trifluoromethyl)benzyl)aniline, 3-(3-amino-5-chloro-2-methylbenzyl)benzonitrile, 5-chloro-2-methyl-3-(3-(trifluoromethoxy)benzyl)aniline, 5-chloro-2-methyl-3-(4-(methylthio)benzyl)aniline, 5-chloro-N1-(6-ethylpyridin-2-yl)-N1,2-dimethylbenzene-1,3-diamine, 5-fluoro-N1-(3-fluoro-4-methoxyphenyl)-2-methylbenzene-1,3-diamine, 2-chloro-N1-(3-fluoro-4-methoxyphenyl)-5-methylbenzene-1,3-diamine, 5-chloro-N1-(3-fluoro-4-methoxyphenyl)-2-methylbenzene-1,3-diamine, 5-fluoro-N1-(3-fluoro-4-methoxyphenyl)-N1,2-dimethylbenzene-1,3-diamine, 2-chloro-N1-(3-fluoro-4-methoxyphenyl)-N1,5-dimethylbenzene-1,3-diamine, 5-fluoro-2-methyl-3-(3-nitrobenzyl)aniline, 5-fluoro-2-methyl-3-(pyridin-3-ylmethyl)aniline, 3-(4-fluorobenzyl)-5-methoxy-2-methylaniline, 5-methoxy-2-methyl-3-(2-methylbenzyl)aniline, 5-methoxy-2-methyl-3-(4-methylbenzyl)aniline, 3-(3-chlorobenzyl)-5-methoxy-2-methylaniline, 3-(2-chlorobenzyl)-5-methoxy-2-methylaniline, 3-(2-fluorobenzyl)-5-methoxy-2-methylaniline, 5-chloro-N1-(3-fluoro-4-methoxyphenyl)-N1,2-dimethylbenzene-1,3-diamine, 5-methoxy-N1-(2-methoxyphenyl)-2-methylbenzene-1,3-diamine, N1-(3-fluoro-4-methoxyphenyl)-5-methoxy-2-methylbenzene-1,3-diamine, 5-methoxy-N1-(2-methoxyphenyl)-N1,2-dimethylbenzene-1,3-diamine, N1-(3-fluoro-4-methoxyphenyl)-5-methoxy-N1,2-dimethylbenzene-1,3-diamine, 5-methoxy-2-methyl-N1-(6-(trifluoromethyl)pyridin-2-yl)benzene-1,3-diamine, 5-fluoro-2-methyl-N1-(6-(trifluoromethyl)pyridin-2-yl)benzene-1,3-diamine, 5-chloro-2-methyl-N1-(6-(trifluoromethyl)pyridin-2-yl)benzene-1,3-diamine, 2-chloro-N1-(4-fluoro-3-methoxyphenyl)-5-methylbenzene-1,3-diamine, N1-(4-fluoro-3-methoxyphenyl)-5-methoxy-2-methylbenzene-1,3-diamine, 3-(3-fluorobenzyl)-5-methoxy-2-methylaniline, 5-methoxy-2-methyl-3-(3-methylbenzyl)aniline, 3-(4-chlorobenzyl)-5-methoxy-2-methylaniline, 5-methoxy-2-methyl-3-(3-nitrobenzyl)aniline, 3-(5-fluoro-2-methylbenzyl)-5-methoxy-2-methylaniline, 3-(3-chloro-4-fluorobenzyl)-5-methoxy-2-methylaniline, 2-chloro-5-methyl-N1-(6-(trifluoromethyl)pyridin-2-yl)benzene-1,3-diamine, N1-(4-fluoro-3-methoxyphenyl)-5-methoxy-N1,2-dimethylbenzene-1,3-diamine, 5-methoxy-N1,2-dimethyl-N1-(6-(trifluoromethyl)pyridin-2-yl)benzene-1,3-diamine, 3-(3,4-difluorobenzyl)-5-methoxy-2-methylaniline, 3-(4-bromobenzyl)-5-methoxy-2-methylaniline, 2-chloro-N1-(4-fluoro-3-methoxyphenyl)-N1,5-dimethylbenzene-1,3-diamine, 5-chloro-N1,2-dimethyl-N1-(6-(trifluoromethyl)pyridin-2-yl)benzene-1,3-diamine, 2-chloro-N1,5-dimethyl-N1-(6-(trifluoromethyl)pyridin-2-yl)benzene-1,3-diamine, 5-fluoro-N1,2-dimethyl-N1-(6-(trifluoromethyl)pyridin-2-yl)benzene-1,3-diamine, 3-(3-fluoro-5-methylbenzyl)-5-methoxy-2-methylaniline, 3-(2-chloro-5-fluorobenzyl)-5-methoxy-2-methylaniline, 3-(2-bromobenzyl)-5-methoxy-2-methylaniline, 5-methoxy-2-methyl-3-(4-(trifluoromethyl)benzyl)aniline, 5-methoxy-2-methyl-3-(3-(trifluoromethyl)benzyl)aniline, 3-amino-5-(3-fluorobenzyl)-4-methylbenzonitrile, 3-benzyl-5-methoxy-2-methylaniline, 5-methoxy-2-methyl-3-(2-(trifluoromethoxy)benzyl)aniline, 5-methoxy-2-methyl-N1-(2-(trifluoromethoxy)phenyl)benzene-1,3-diamine, 5-chloro-2-methyl-N1-(2-(trifluoromethoxy)phenyl)benzene-1,3-diamine, 2-chloro-5-methyl-N1-(2-(trifluoromethoxy)phenyl)benzene-1,3-diamine, 5-fluoro-2-methyl-N1-(2-(trifluoromethoxy)phenyl)benzene-1,3-diamine, 1-(3-amino-5-fluoro-2-methylphenyl)-2-(2-chloro-4-methoxyphenoxy)ethan-1-one, 5-methoxy-2-methyl-3-(3-(trifluoromethoxy)benzyl)aniline, 3-(3-amino-5-methoxy-2-methylbenzyl)benzonitrile, 5-methoxy-2-methyl-3-(2-(trifluoromethyl)benzyl)aniline, 3-amino-5-benzyl-4-methylbenzonitrile, 3-amino-5-(3-cyanobenzyl)-4-methylbenzonitrile, 3-amino-5-(4-fluorobenzyl)-4-methylbenzonitrile, 3-amino-5-(4-chlorobenzyl)-4-methylbenzonitrile, 3-amino-4-methyl-5-(3-nitrobenzyl)benzonitrile, 3-amino-5-(3-bromobenzyl)-4-methylbenzonitrile and 3-amino-4-methyl-5-(2-(trifluoromethoxy)benzyl)benzonitrile.
Dependencies are inferred from the claim text.