1-3-bis(substituted phenyl)-3-hydroxypropan-1-one or 2-propen-1-one compound, and salt thereof
There is provided a novel process intermediate represented by the general formula (1) or (2): (where, X represents halogen atom, cyano group or the like, Y represents halogen atom, cyano group or the like, R 1 represents C 1 -C 6 haloalkyl group or C 3 -C 8 halocycloalkyl group, R 2 represents methyl group, halogen atom, cyano group or the like, m represents an integer of 1 to 5, and n represents an integer of 1 to 4).
1. A 1,3-bis(substituted phenyl)-3-substituent-3-hydroxypropan-1-one compound or salt thereof represented by general formula (1):
(where, X represents halogen atom, or C 1 -C 4 haloalkyl group, and when m represents 2 or 3, each X can be identical with or different from each other;
Y represents halogen atom, nitro group, C 1 -C 4 alkyl group, or C 1 -C 4 haloalkyl group,
R 1 represents C 1 -C 4 haloalkyl group;
R 2 represents methyl group, halogen atom, cyano group, nitro group, —NH 2 , —N(R 5 )R 4 , —OH, —OR 3 , benzyloxy group, —OSO 2 R 3 , phenylsulfonyloxy group, phenylsulfonyloxy group substituted by (Z) p1 , —C(O)OH, —C(O)OR 3 , —C(O)NH 2 , —C(O)N(R b )R a , or —C(S)N(R b )R a ;
R 3 represents C 1 -C 6 alkyl group, C 1 -C 4 alkoxy(C 1 -C 4 )alkyl group, C 1 -C 6 haloalkyl group, or C 1 -C 3 haloalkoxy(C 1 -C 3 )haloalkyl group;
R 4 represents C 1 -C 6 alkyl group, —CHO, C 1 -C 6 alkylcarbonyl group, C 1 -C 6 haloalkylcarbonyl group, C 1 -C 6 alkoxycarbonyl group, C 1 -C 6 alkylthiocarbonyl group, C 1 -C 6 alkoxythiocarbonyl group, C 1 -C 6 alkyldithiocarbonyl group, C 1 -C 6 alkylsulfonyl group, or C 1 -C 6 haloalkylsulfonyl group;
R 5 represents hydrogen atom or C 1 -C 6 alkyl group;
R a represents C 1 -C 6 alkyl group, (C 1 -C 6 ) alkyl group substituted arbitrarily by R 6 , C 3 -C 6 cycloalkyl group, C 3 -C 6 alkenyl group, C 3 -C 6 haloalkenyl group, C 3 -C 6 alkynyl group, —N(R 9 )R 8 , —C(O)OR 7 , —C(O)NH 2 , —C(O)NHR 7 , —C(R 15 )═NOR 14 , phenyl group, phenyl group substituted by (Z) p1 , D-5, D-7, D-10, D-11, D-12, D-14, D-15, D-18, D-31, D-32, D-38, D-39, D-41, D-42, D-44, E-1, E-2, E-3, E-4, or E-7;
R b represents hydrogen atom, C 1 -C 6 alkyl group, C 1 -C 4 alkoxy(C 1 -C 4 )alkyl group, cyano(C 1 -C 6 )alkyl group, C 3 -C 6 alkynyl group, —C(O)R 7 , or —C(O)OR 7 ;
R 6 represents halogen atom, cyano group, C 3 -C 6 cycloalkyl group, C 3 -C 6 halocycloalkyl group, C 1 -C 6 alkoxy group, C 1 -C 6 haloalkoxy group, C 1 -C 6 alkylthio group, C 1 -C 6 haloalkylthio group, C 1 -C 6 alkylsulfinyl group, C 1 -C 6 haloalkylsulfinyl group, C 1 -C 6 alkylsulfonyl group, C 1 -C 6 haloalkylsulfonyl group, —C(O)R 12 , —C(O)OR 12 , —C(O)NH 2 , —C(O)N(R 13 )R 12 , —C(S)NH 2 , —C(S)N(R 13 )R 12 , —C(R 15 )═NOH, —C(R 15 )═NOR 14 , phenyl group, phenyl group substituted by (Z) p1 , D-1 to D-46, or E-1 to E-8;
the D-1 to D-46 represent respective aromatic heterocycles as shown in the following structural formulae:
Z represents halogen atom, cyano group, nitro group, C 1 -C 6 alkyl group, C 1 -C 6 haloalkyl group, C 1 -C 6 alkoxy group, C 1 -C 6 haloalkoxy group, C 1 -C 6 alkylsulfonyl group, C 1 -C 6 haloalkylsulfonyl group, C 1 -C 6 alkoxycarbonyl group, —C(O)NH 2 , C 1 -C 6 alkylaminocarbonyl group, di(C 1 -C 6 alkyl)aminocarbonyl group, —C(S)NH 2 , —S(O) 2 NH 2 , C 1 -C 6 alkylaminosulfonyl group or di(C 1 -C 6 alkyl)aminosulfonyl group, and when p1, p2, p3, or p4 represents 2 or higher integer, each Z can be identical with or different from each other;
E-1 to E-8 represent respective saturated heterocycles as shown in the following structural formulae:
R 7 represents C 1 -C 6 alkyl group, C 1 -C 6 haloalkyl group, C 1 -C 6 alkoxy(C 1 -C 4 )alkyl group, C 1 -C 6 alkylthio(C 1 -C 4 )alkyl group, C 3 -C 8 cycloalkyl group, C 3 -C 6 alkenyl group, or C 3 -C 6 alkynyl group;
R 8 represents C 1 -C 6 haloalkyl group, —C(O)R 12 , —C(O)OR 12 , phenyl group, phenyl group substituted by (Z) p1 , D-3, D-4, D-18, D-38, D-41, D-42, D-44, or D-45;
R 9 represents hydrogen atom, C 1 -C 6 alkyl group, or C 3 -C 6 alkynyl group;
R 10 represents C 1 -C 6 alkyl group, phenyl group, or phenyl group substituted by (Z) p1 ;
R 11 represents C 1 -C 4 alkyl group, when q1, q2, q3, or q4 represents 2 or higher integer, each R 11 can be identical with or different from each other, and two R 11 s substituting on the same carbon atom indicate that the two R 11 s can form an oxo ring together;
R 12 represents C 1 -C 6 alkyl group, C 1 -C 6 haloalkyl group, C 3 -C 6 cycloalkyl(C 1 -C 4 )alkyl group, C 3 -C 6 cycloalkyl group, C 3 -C 6 alkenyl group, or C 3 -C 6 alkynyl group;
R 13 represents hydrogen atom or C 1 -C 6 alkyl group;
R 14 represents C 1 -C 6 alkyl group or C 1 -C 6 haloalkyl group;
R 15 represents hydrogen atom or C 1 -C 6 alkyl group;
m represents an integer of 1 to 3;
n represents an integer of 0 or 1;
p1 represents an integer of 1 to 5;
p2 represents an integer of 0 to 4;
p3 represents an integer of 0 to 3;
p4 represents an integer of 0 to 2;
p5 represents an integer of 0 or 1;
q2 represents an integer of 0 to 5;
q3 represents an integer of 0 to 7;
q4 represents an integer of 0 to 9;
r represents an integer of 0 to 2; and
t represents an integer of 0 or 1).
2. The 1,3-bis(substituted phenyl)-3-substituent-3-hydroxypropan-1-one compound or salt thereof according to claim 1 , which is represented by the formula, where R 2 represents halogen atom, cyano group, nitro group, —NH 2 , —NHR 4 , —OH, —OR 3 , benzyloxy group, —OSO 2 R 3 , phenylsulfonyloxy group, paratoluenesulfonyloxy group, —C(O)OH, —C(O)OR 3 , —C(O)NH 2 , or —C(O)N(R b )R a ;
R 3 represents C 1 -C 4 alkyl group or C 1 -C 4 haloalkyl group;
R 4 represents C 1 -C 4 alkyl group, —CHO, C 1 -C 4 alkylcarbonyl group, or C 1 -C 4 alkoxycarbonyl group;
R a represents C 1 -C 4 alkyl group, (C 1 -C 4 ) alkyl group substituted arbitrarily by R 6 , —N(R 9 )R 8 , —C(O)OR 7 , —C(O)NH 2 , —C(O)NHR 7 , —C(R 15 )═NOR 14 , phenyl group, phenyl group substituted by (Z) p1 , D-5, D-7, D-10, D-11, D-12, D-14, D-15, D-18, D-31, D-32, D-38, D-39, D-41, D-42, D-44, E-1, or E-7;
R b represents hydrogen atom, C 1 -C 6 alkyl group, C 1 -C 4 alkoxy(C 1 -C 4 )alkyl group, cyano(C 1 -C 4 )alkyl group, C 3 -C 6 alkynyl group, —C(O)R 7 , or —C(O)OR 7 ;
R 6 represents halogen atom, cyano group, C 3 -C 6 cycloalkyl group, C 1 -C 4 alkoxy group, C 1 -C 4 haloalkoxy group, C 1 -C 4 alkylthio group, C 1 -C 4 haloalkylthio group, C 1 -C 4 alkylsulfonyl group, C 1 -C 4 haloalkylsulfonyl group, —C(O)N(R 13 )R 12 , —C(R 15 )═NOH, —C(R 15 )═NOR 14 , phenyl group, phenyl group substituted by (Z) p1 , D-11 to D-14, D-18, D-19, D-25, D-26, D-31, D-32, D-36, D-38, D-41, D-44, D-45, E-1, E-2, or E-5;
Z represents halogen atom, cyano group, nitro group, C 1 -C 4 alkyl group, C 1 -C 4 haloalkyl group, C 1 -C 4 alkoxy group, C 1 -C 4 haloalkoxy group, C 1 -C 4 alkylsulfonyl group, or C 1 -C 4 haloalkylsulfonyl group, and when p1, p2, p3, or p4 represents 2 or higher integer, each Z can be identical with or different from each other;
R 7 represents C 1 -C 6 alkyl group, C 1 -C 6 haloalkyl group, C 1 -C 6 alkoxy(C 1 -C 4 )alkyl group, C 1 -C 6 alkylthio(C 1 -C 4 )alkyl group, C 3 -C 8 cycloalkyl group, C 3 -C 6 alkenyl group, or C 3 -C 6 alkynyl group;
R 8 represents C 1 -C 4 haloalkyl group, —C(O)R 12 , —C(O)OR 12 , phenyl group, phenyl group substituted by (Z) p1 , D-3, D-4, D-18, D-38, D-41, D-42, D-44, or D-45;
R 9 represents hydrogen atom or C 1 -C 6 alkyl group;
R 10 represents C 1 -C 4 alkyl group;
R 11 represents C 1 -C 4 alkyl group, when q1, q2, q3, or q4 represents 2 or higher integer, each R 11 can be identical with or different from each other, and two R 11 s substituting on the same carbon atom indicate that the two R 11 s can form an oxo ring together;
R 12 represents C 1 -C 4 alkyl group, C 1 -C 4 haloalkyl group, C 3 -C 6 cycloalkyl(C 1 -C 4 ) alkyl group, C 3 -C 6 cycloalkyl group, C 3 -C 6 alkenyl group, or C 3 -C 6 alkynyl group;
R 13 represents hydrogen atom or C 1 -C 4 alkyl group;
R 14 represents C 1 -C 4 alkyl group or C 1 -C 4 haloalkyl group; and
R 15 represents hydrogen atom or C 1 -C 4 alkyl group.
3. A 1,3-bis(substituted phenyl)-3-substituent-2-propen-1-one compound or salt thereof represented by general formula (2):
(where, X represents halogen atom, cyano group, nitro group, —SF 5 , C 1 -C 6 alkyl group, C 1 -C 6 haloalkyl group, hydroxy(C 1 -C 6 )haloalkyl group, C 1 -C 6 alkoxy(C 1 -C 6 )haloalkyl group, C 1 -C 6 haloalkoxy(C 1 -C 6 )haloalkyl group, C 3 -C 8 halocycloalkyl group, —OR 3 , —OSO 2 R 3 , or —S(O) r R 3 , and when m represents 2 or higher integer, each X can be identical with or different from each other;
Y represents halogen atom, cyano group, nitro group, C 1 -C 4 alkyl group, C 1 -C 4 haloalkyl group, C 1 -C 4 alkoxy group, C 1 -C 4 haloalkoxy group, C 1 -C 6 alkylthio group, C 1 -C 6 haloalkylthio group, C 1 -C 6 alkylsulfonyl group, C 1 -C 6 haloalkylsulfonyl group, —NH 2 or —N(R 5 )R 4 , and when n represents 2 or higher integer, each Y can be identical with or different from each other;
R 1 represents C 1 -C 6 haloalkyl group or C 3 -C 8 halocycloalkyl group;
R 2 represents methyl group, halogen atom, cyano group, nitro group, —NH 2 , —N(R 5 )R 4 , —OH, —OR 3 , benzyloxy group, —OSO 2 R 3 , phenylsulfonyloxy group, phenylsulfonyloxy group substituted by (Z) p1 , —C(O)OH, —C(O)OR 3 , —C(O)NH 2 , —C(O)N(R b )R a or —C(S)N(R b )R a ;
R 3 represents C 1 -C 6 alkyl group, C 1 -C 4 alkoxy(C 1 -C 4 )alkyl group, C 1 -C 6 haloalkyl group or C 1 -C 3 haloalkoxy(C 1 -C 3 )haloalkyl group;
R 4 represents C 1 -C 6 alkyl group, —CHO, C 1 -C 6 alkylcarbonyl group, C 1 -C 6 haloalkylcarbonyl group, C 1 -C 6 alkoxycarbonyl group, C 1 -C 6 alkyithiocarbonyl group, C 1 -C 6 alkoxythiocarbonyl group, C 1 -C 6 alkyldithiocarbonyl group, C 1 -C 6 alkylsulfonyl group, or C 1 -C 6 haloalkylsulfonyl group;
R 5 represents hydrogen atom or C 1 -C 6 alkyl group;
R a represents C 1 -C 6 alkyl group, (C 1 -C 6 ) alkyl group substituted arbitrarily by R 6 , C 3 -C 6 cycloalkyl group, C 3 -C 6 alkenyl group, C 3 -C 6 haloalkenyl group, C 3 -C 6 alkynyl group, —N(R 9 )R 8 , —C(O)OR 7 , —C(O)NH 2 , —C(O)NHR 7 , —C(R 15 )═NOR 14 , phenyl group, phenyl group substituted by (Z) p1 , D-5, D-7, D-10, D-11, D-12, D-14, D-15, D-18, D-31, D-32, D-38, D-39, D-41, D-42, D-44, E-1, E-2, E-3, E-4, or E-7;
R b represents hydrogen atom, C 1 -C 6 alkyl group, C 1 -C 4 alkoxy(C 1 -C 4 )alkyl group, cyano(C 1 -C 6 )alkyl group, C 3 -C 6 alkynyl group, —C(O)R 7 , or —C(O)OR 7 ;
R 6 represents halogen atom, cyano group, C 3 -C 6 cycloalkyl group, C 3 -C 6 halocycloalkyl group, C 1 -C 6 alkoxy group, C 1 -C 6 haloalkoxy group, C 1 -C 6 alkylthio group, C 1 -C 6 haloalkylthio group, C 1 -C 6 alkylsulfinyl group, C 1 -C 6 haloalkylsulfinyl group, C 1 -C 6 alkylsulfonyl group, C 1 -C 6 haloalkylsulfonyl group, —C(O)R 12 , —C(O)OR 12 , —C(O)NH 2 , —C(O)N(R 13 )R 12 , —C(S)NH 2 , —C(S)N(R 13 )R 12 , —C(R 15 )═NOH, —C(R 15 )═NOR 14 , phenyl group, phenyl group substituted by (Z) p1 , D-1 to D-46, or E-1 to E-8;
the D-1 to D-46 represent respective aromatic heterocycles as shown in the following structural formulae:
Z represents halogen atom, cyano group, nitro group, C 1 -C 6 alkyl group, C 1 -C 6 haloalkyl group, C 1 -C 6 alkoxy group, C 1 -C 6 haloalkoxy group, C 1 -C 6 alkylsulfonyl group, C 1 -C 6 haloalkylsulfonyl group, C 1 -C 6 alkoxycarbonyl group, —C(O)NH 2 , C 1 -C 6 alkylaminocarbonyl group, di(C 1 -C 6 alkyl)aminocarbonyl group, —C(S)NH 2 , —S(O) 2 NH 2 , C 1 -C 6 alkylaminosulfonyl group or di(C 1 -C 6 alkyl)aminosulfonyl group, and when p1, p2, p3, or p4 represents 2 or higher integer, each Z can be identical with or different from each other;
the E-1 to E-8 represent respective saturated heterocycles as shown in the following structural formulae:
R 7 represents C 1 -C 6 alkyl group, C 1 -C 6 haloalkyl group, C 1 -C 6 alkoxy(C 1 -C 4 )alkyl group, C 1 -C 6 alkylthio(C 1 -C 4 )alkyl group, C 3 -C 8 cycloalkyl group, C 3 -C 6 alkenyl group, or C 3 -C 6 alkynyl group;
R 8 represents C 1 -C 6 haloalkyl group, —C(O)R 12 , —C(O)OR 12 , phenyl group, phenyl group substituted by (Z) p1 , D-3, D-4, D-18, D-38, D-41, D-42, D-44, or D-45;
R 9 represents hydrogen atom, C 1 -C 6 alkyl group, or C 3 -C 6 alkynyl group;
R 10 represents C 1 -C 6 alkyl group, phenyl group, or phenyl group substituted by (Z) p1 ;
R 11 represents C 1 -C 4 alkyl group, when q1, q2, q3, or q4 represents 2 or higher integer, each R 11 can be identical with or different from each other, and two R 11 s substituting on the same carbon atom indicate that the two R 11 s can form an oxo ring together;
R 12 represents C 1 -C 6 alkyl group, C 1 -C 6 haloalkyl group, C 3 -C 6 cycloalkyl(C 1 -C 4 )alkyl group, C 3 -C 6 cycloalkyl group, C 3 -C 6 alkenyl group, or C 3 -C 6 alkynyl group;
R 13 represents hydrogen atom or C 1 -C 6 alkyl group;
R 14 represents C 1 -C 6 alkyl group or C 1 -C 6 haloalkyl group;
R 15 represents hydrogen atom or C 1 -C 6 alkyl group;
m represents an integer of 1 to 5;
n represents an integer of 0 to 4;
p1 represents an integer of 1 to 5;
p2 represents an integer of 0 to 4;
p3 represents an integer of 0 to 3;
p4 represents an integer of 0 to 2;
p5 represents an integer of 0 or 1;
q2 represents an integer of 0 to 5;
q3 represents an integer of 0 to 7;
q4 represents an integer of 0 to 9;
r represents an integer of 0 to 2; and
t represents an integer of 0 or 1).
4. The 1,3-bis(substituted phenyl)-3-substituent-2-propen-1-one compound or salt thereof according to claim 3 which is represented by the formula, where X represents halogen atom or C 1 -C 4 haloalkyl group, and when m represents 2 or 3, each X can be identical with or different from each other;
Y represents halogen atom, nitro group, C 1 -C 4 alkyl group, or C 1 -C 4 haloalkyl group;
R 1 represents C 1 -C 4 haloalkyl group;
m represents an integer of 1 to 3; and
n represents 0 or 1.
5. The 1,3-bis(substituted phenyl)-3-substituent-2-propen-1-one compound or salt thereof according to claim 4 which is represented by the formula, where R 2 represents halogen atom, cyano group, nitro group, —NH 2 , —NHR 4 , —OH, —OR 3 , benzyloxy group, —OSO 2 R 3 , phenylsulfonyloxy group, paratoluenesulfonyloxy group, —C(O)OH, —C(O)OR 3 , —C(O)NH 2 , or —C(O)N(R b )R a ;
R 3 represents C 1 -C 4 alkyl group or C 1 -C 4 haloalkyl group;
R 4 represents C 1 -C 4 alkyl group, —CHO, C 1 -C 4 alkylcarbonyl group, or C 1 -C 4 alkoxycarbonyl group;
R a represents C 1 -C 4 alkyl group, (C 1 -C 4 ) alkyl group substituted arbitrarily by R 6 , —N(R 9 )R 8 , —C(O)OR 7 , —C(O)NH 2 , —C(O)NHR 7 , —C(R 15 )═NOR 14 , phenyl group, phenyl group substituted by (Z) p1 , D-5, D-7, D-10, D-11, D-12, D-14, D-15, D-18, D-31, D-32, D-38, D-39, D-41, D-42, D-44, E-1, or E-7;
R b represents hydrogen atom, C 1 -C 6 alkyl group, C 1 -C 4 alkoxy(C 1 -C 4 )alkyl group, cyano(C 1 -C 4 )alkyl group, C 3 -C 6 alkynyl group, —C(O)R 7 , or —C(O)OR 7 ;
R 6 represents halogen atom, cyano group, C 3 -C 6 cycloalkyl group, C 1 -C 4 alkoxy group, C 1 -C 4 haloalkoxy group, C 1 -C 4 alkylthio group, C 1 -C 4 haloalkylthio group, C 1 -C 4 alkylsulfonyl group, C 1 -C 4 haloalkylsulfonyl group, —C(O)N(R 13 )R 12 , —C(R 15 )═NOH, —C(R 15 )═NOR 14 , phenyl group, phenyl group substituted by (Z) p1 , D-11 to D-14, D-18, D-19, D-25, D-26, D-31, D-32, D-36, D-38, D-41, D-44, D-45, E-1, E-2, or E-5;
Z represents halogen atom, cyano group, nitro group, C 1 -C 4 alkyl group, C 1 -C 4 haloalkyl group, C 1 -C 4 alkoxy group, C 1 -C 4 haloalkoxy group, C 1 -C 4 alkylsulfonyl group, or C 1 -C 4 haloalkylsulfonyl group, and when p1, p2, p3, or p4 represents 2 or higher integer, each Z can be identical with or different from each other;
R 7 represents C 1 -C 6 alkyl group, C 1 -C 6 haloalkyl group, C 1 -C 6 alkoxy(C 1 -C 4 )alkyl group, C 1 -C 6 alkylthio(C 1 -C 4 )alkyl group, C 3 -C 8 cycloalkyl group, C 3 -C 6 alkenyl group, or C 3 -C 6 alkynyl group;
R 8 represents C 1 -C 4 haloalkyl group, —C(O)R 12 , —C(O)OR 12 , phenyl group, phenyl group substituted by (Z) p1 , D-3, D-4, D-18, D-38, D-41, D-42, D-44, or D-45;
R 9 represents hydrogen atom or C 1 -C 6 alkyl group;
R 10 represents C 1 -C 4 alkyl group;
R 11 represents C 1 -C 4 alkyl group, when q1, q2, q3, or q4 represents 2 or higher integer, each R 11 can be identical with or different from each other, and two R 11 s substituting on the same carbon atom indicate that the two R 11 s can form an oxo ring together;
R 12 represents C 1 -C 4 alkyl group, C 1 -C 4 haloalkyl group, C 3 -C 6 cycloalkyl(C 1 -C 4 )alkyl group, C 3 -C 6 cycloalkyl group, C 3 -C 6 alkenyl group, or C 3 -C 6 alkynyl group;
R 13 represents hydrogen atom or C 1 -C 4 alkyl group;
R 14 represents C 1 -C 4 alkyl group or C 1 -C 4 haloalkyl group; and
R 15 represents hydrogen atom or C 1 -C 4 alkyl group.