1-3-bis(substituted phenyl)-3-hydroxypropan-1-one or 2-propen-1-one compound, and salt thereof
AssigneeNissan Chemical Industries, Ltd.
InventorsTakashi Mizukoshi, Yasuhiro Sakurai, Kazutaka Matoba, Manabu Yaosaka
Life of this patent
Estimating the term…
Abstract
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, R1 represents C1-C6 haloalkyl group or C3-C8 halocycloalkyl group, R2 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).
Claims5
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 C1-C4 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, C1-C4 alkyl group, or C1-C4 haloalkyl group,
- R1 represents C1-C4 haloalkyl group;
- R2 represents methyl group, halogen atom, cyano group, nitro group, —NH2, —N(R5)R4, —OH, —OR3, benzyloxy group, —OSO2R3, phenylsulfonyloxy group, phenylsulfonyloxy group substituted by (Z)p1, —C(O)OH, —C(O)OR3, —C(O)NH2, —C(O)N(Rb)Ra, or —C(S)N(Rb)Ra;
- R3 represents C1-C6 alkyl group, C1-C4 alkoxy(C1-C4)alkyl group, C1-C6 haloalkyl group, or C1-C3 haloalkoxy(C1-C3)haloalkyl group;
- R4 represents C1-C6 alkyl group, —CHO, C1-C6 alkylcarbonyl group, C1-C6 haloalkylcarbonyl group, C1-C6 alkoxycarbonyl group, C1-C6 alkylthiocarbonyl group, C1-C6 alkoxythiocarbonyl group, C1-C6 alkyldithiocarbonyl group, C1-C6 alkylsulfonyl group, or C1-C6 haloalkylsulfonyl group;
- R5 represents hydrogen atom or C1-C6 alkyl group;
- Ra represents C1-C6 alkyl group, (C1-C6) alkyl group substituted arbitrarily by R6, C3-C6 cycloalkyl group, C3-C6 alkenyl group, C3-C6 haloalkenyl group, C3-C6 alkynyl group, —N(R9)R8, —C(O)OR7, —C(O)NH2, —C(O)NHR7, —C(R15)═NOR14, 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;
- Rb represents hydrogen atom, C1-C6 alkyl group, C1-C4 alkoxy(C1-C4)alkyl group, cyano(C1-C6)alkyl group, C3-C6 alkynyl group, —C(O)R7, or —C(O)OR7;
- R6 represents halogen atom, cyano group, C3-C6 cycloalkyl group, C3-C6 halocycloalkyl group, C1-C6 alkoxy group, C1-C6 haloalkoxy group, C1-C6 alkylthio group, C1-C6 haloalkylthio group, C1-C6 alkylsulfinyl group, C1-C6 haloalkylsulfinyl group, C1-C6 alkylsulfonyl group, C1-C6 haloalkylsulfonyl group, —C(O)R12, —C(O)OR12, —C(O)NH2, —C(O)N(R13)R12, —C(S)NH2, —C(S)N(R13)R12, —C(R15)═NOH, —C(R15)═NOR14, 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, C1-C6 alkyl group, C1-C6 haloalkyl group, C1-C6 alkoxy group, C1-C6 haloalkoxy group, C1-C6 alkylsulfonyl group, C1-C6 haloalkylsulfonyl group, C1-C6 alkoxycarbonyl group, —C(O)NH2, C1-C6 alkylaminocarbonyl group, di(C1-C6 alkyl)aminocarbonyl group, —C(S)NH2, —S(O)2NH2, C1-C6 alkylaminosulfonyl group or di(C1-C6 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:
- R7 represents C1-C6 alkyl group, C1-C6 haloalkyl group, C1-C6 alkoxy(C1-C4)alkyl group, C1-C6 alkylthio(C1-C4)alkyl group, C3-C8 cycloalkyl group, C3-C6 alkenyl group, or C3-C6 alkynyl group;
- R8 represents C1-C6 haloalkyl group, —C(O)R12, —C(O)OR12, 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;
- R9 represents hydrogen atom, C1-C6 alkyl group, or C3-C6 alkynyl group;
- R10 represents C1-C6 alkyl group, phenyl group, or phenyl group substituted by (Z)p1;
- R11 represents C1-C4 alkyl group, when q1, q2, q3, or q4 represents 2 or higher integer, each R11 can be identical with or different from each other, and two R11s substituting on the same carbon atom indicate that the two R11s can form an oxo ring together;
- R12 represents C1-C6 alkyl group, C1-C6 haloalkyl group, C3-C6 cycloalkyl(C1-C4)alkyl group, C3-C6 cycloalkyl group, C3-C6 alkenyl group, or C3-C6 alkynyl group;
- R13 represents hydrogen atom or C1-C6 alkyl group;
- R14 represents C1-C6 alkyl group or C1-C6 haloalkyl group;
- R15 represents hydrogen atom or C1-C6 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).
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, —SF5, C1-C6 alkyl group, C1-C6 haloalkyl group, hydroxy(C1-C6)haloalkyl group, C1-C6 alkoxy(C1-C6)haloalkyl group, C1-C6 haloalkoxy(C1-C6)haloalkyl group, C3-C8 halocycloalkyl group, —OR3, —OSO2R3, or —S(O)rR3, 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, C1-C4 alkyl group, C1-C4 haloalkyl group, C1-C4 alkoxy group, C1-C4 haloalkoxy group, C1-C6 alkylthio group, C1-C6 haloalkylthio group, C1-C6 alkylsulfonyl group, C1-C6 haloalkylsulfonyl group, —NH2 or —N(R5)R4, and when n represents 2 or higher integer, each Y can be identical with or different from each other;
- R1 represents C1-C6 haloalkyl group or C3-C8 halocycloalkyl group;
- R2 represents methyl group, halogen atom, cyano group, nitro group, —NH2, —N(R5)R4, —OH, —OR3, benzyloxy group, —OSO2R3, phenylsulfonyloxy group, phenylsulfonyloxy group substituted by (Z)p1, —C(O)OH, —C(O)OR3, —C(O)NH2, —C(O)N(Rb)Ra or —C(S)N(Rb)Ra;
- R3 represents C1-C6 alkyl group, C1-C4 alkoxy(C1-C4)alkyl group, C1-C6 haloalkyl group or C1-C3 haloalkoxy(C1-C3)haloalkyl group;
- R4 represents C1-C6 alkyl group, —CHO, C1-C6 alkylcarbonyl group, C1-C6 haloalkylcarbonyl group, C1-C6 alkoxycarbonyl group, C1-C6 alkyithiocarbonyl group, C1-C6 alkoxythiocarbonyl group, C1-C6 alkyldithiocarbonyl group, C1-C6 alkylsulfonyl group, or C1-C6 haloalkylsulfonyl group;
- R5 represents hydrogen atom or C1-C6 alkyl group;
- Ra represents C1-C6 alkyl group, (C1-C6) alkyl group substituted arbitrarily by R6, C3-C6 cycloalkyl group, C3-C6 alkenyl group, C3-C6 haloalkenyl group, C3-C6 alkynyl group, —N(R9)R8, —C(O)OR7, —C(O)NH2, —C(O)NHR7, —C(R15)═NOR14, 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;
- Rb represents hydrogen atom, C1-C6 alkyl group, C1-C4 alkoxy(C1-C4)alkyl group, cyano(C1-C6)alkyl group, C3-C6 alkynyl group, —C(O)R7, or —C(O)OR7;
- R6 represents halogen atom, cyano group, C3-C6 cycloalkyl group, C3-C6 halocycloalkyl group, C1-C6 alkoxy group, C1-C6 haloalkoxy group, C1-C6 alkylthio group, C1-C6 haloalkylthio group, C1-C6 alkylsulfinyl group, C1-C6 haloalkylsulfinyl group, C1-C6 alkylsulfonyl group, C1-C6 haloalkylsulfonyl group, —C(O)R12, —C(O)OR12, —C(O)NH2, —C(O)N(R13)R12, —C(S)NH2, —C(S)N(R13)R12, —C(R15)═NOH, —C(R15)═NOR14, 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, C1-C6 alkyl group, C1-C6 haloalkyl group, C1-C6 alkoxy group, C1-C6 haloalkoxy group, C1-C6 alkylsulfonyl group, C1-C6 haloalkylsulfonyl group, C1-C6 alkoxycarbonyl group, —C(O)NH2, C1-C6 alkylaminocarbonyl group, di(C1-C6 alkyl)aminocarbonyl group, —C(S)NH2, —S(O)2NH2, C1-C6 alkylaminosulfonyl group or di(C1-C6 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:
- R7 represents C1-C6 alkyl group, C1-C6 haloalkyl group, C1-C6 alkoxy(C1-C4)alkyl group, C1-C6 alkylthio(C1-C4)alkyl group, C3-C8 cycloalkyl group, C3-C6 alkenyl group, or C3-C6 alkynyl group;
- R8 represents C1-C6 haloalkyl group, —C(O)R12, —C(O)OR12, 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;
- R9 represents hydrogen atom, C1-C6 alkyl group, or C3-C6 alkynyl group;
- R10 represents C1-C6 alkyl group, phenyl group, or phenyl group substituted by (Z)p1;
- R11 represents C1-C4 alkyl group, when q1, q2, q3, or q4 represents 2 or higher integer, each R11 can be identical with or different from each other, and two R11s substituting on the same carbon atom indicate that the two R11s can form an oxo ring together;
- R12 represents C1-C6 alkyl group, C1-C6 haloalkyl group, C3-C6 cycloalkyl(C1-C4)alkyl group, C3-C6 cycloalkyl group, C3-C6 alkenyl group, or C3-C6 alkynyl group;
- R13 represents hydrogen atom or C1-C6 alkyl group;
- R14 represents C1-C6 alkyl group or C1-C6 haloalkyl group;
- R15 represents hydrogen atom or C1-C6 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).
Dependencies are inferred from the claim text.