Method for producing pyridazinone compounds and intermediate thereof
AssigneeSumitomo Chemical Company, Limited
InventorsMarkus Jachmann, Takayuki Wakamatsu, Mitsuharu Anryu
Life of this patent
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Abstract
The present invention relates to a novel method for producing a pyridazinone compound and an intermediate thereof as shown in the following scheme: wherein the symbols are as defined in the specification.
Claims51
A method for producing a compound of the formula (1):
- which comprises reacting a compound of the formula (2);
- with a compound of the formula (3):
- M(OR1)v (3);
- wherein the symbols in the formulae (1), (2) and (3) are defined as follows:
- R1 represents hydrogen, a C1-C6 alkyl group or a phenyl group;
- wherein the C1-C6 alkyl group may be optionally substituted with one or more halogens, provided that when it is substituted with two or more halogens, then the halogens may be same or different;
- and
- the phenyl group may optionally have one or more substituents selected from Group 1, provided that when it has two or more substituents, then the substituents may be same or different;
- the Group 1 consists of halogen, a cyano group, a nitro group, C1-C6 alkyl group, a C1-C6 alkoxy group, and a (C1-C6 alkoxy)C1-C6 alkyl group;
- in the Group 1, the C1-C6 alkyl group, the C1-C6 alkoxy group, and the (C1-C6 alkoxy)C1-C6 alkyl group may be optionally substituted with one or more halogens, provided that when they are substituted With two or more halogens, then the halogens may be same or different;
- R2 represents hydrogen, a C1-C6 alkyl group, a (C1-C6 alkoxy)C1-C6 alkyl group;
- a C2-C6 alkenyl group, a C2-C6 alkynyl group, a C3-C6 cycloalkyl group, a (C1-C6 alkylthio)C1-C6 alkyl group, a (C1-C6 alkylsulfinyl)C1-C6 alkyl group, a (C1-C6 alkylsulfonyl)C1-C6 alkyl group, a phenyl group, or a 5- or 6-membered heteroaryl group;
- wherein the C1-C6 alkyl group, the (C1-C6 alkoxy)C1-C6 alkyl group, the C2-C6 alkenyl group, the C2-C6 alkynyl group, the C3-C6 cycloalkyl group, the (C1-C6 alkylthio)C1-C6 alkyl group, the (C1-C6 alkylsulfinyl)C1-C6 alkyl group, and the (C1-C6 alkylsulfonyl)C1-C6 alkyl group may be optionally substituted with one or more halogens, provided that when they are substituted with two or more halogens, then the halogens may be same or different;
- and
- the phenyl group and the 5- or 6-membered heteroaryl group may optionally have one or more substituents selected from Group 2, provided that when they have two or more substituents, then the substituents may be same or different;
- the Group 2 consists of halogen, a cyano group, a nitro group, a formyl group, a C1-C6 alkyl group, a C1-C6 alkoxy group, a (C1-C6 alkoxy)C1-C6 alkyl group, a C2-C6 alkenyl group, a C2-C6 alkynyl group, a C3-C6 cycloalkyl group, a C1-C6 alkylthio group, a C1-C6 alkylsulfinyl group, a C1-C6 alkylsulfonyl group, a C1-C6 alkylamino group, a di(C1-C6 alkyl)amino group, a C3-C6 cycloalkylamino group, a (C1-C6 alkyl)carbonyl group, a (C3-C6 cycloalkyl)carbonyl group, a (C1-C6 alkoxy)carbonyl group, a (C1-C6 alkylamino)carbonyl group, a di(C1-C6 alkyl)aminocarbonyl group, a (C3-C6 cycloalkylamino)carbonyl group, and a tri(C1-C6 alkyl)silyl group;
- in the Group 2, the C1-C6 alkyl group, the C1-C6 alkoxy group, the (C1-C6 alkoxy alkyl group, the C2-C6 alkenyl group, the C2-C6 alkynyl group, the C3-C6 cycloalkyl group, the C1-C6 alkylthio group, the C1-C6 alkylsulfinyl group, the C1-C6 alkylsulfonyl group, the (C1-C6 alkyl)carbonyl group, the (C3-C6 cycloalkyl)carbonyl group, and the (C1-C6 alkoxy)carbonyl group may be optionally substituted with one or more halogens, provided that when they are substituted with two or more halogens, then the halogens may be same or different;
- R3 represents hydrogen, a C1-C6 alkyl group, a (C1-C6 alkoxy)C1-C6 alkyl group, a C2-C6 alkenyl group, a C2-C6 alkynyl group, a C3-C6 cycloalkyl group, a (C1-C6 alkylthio)C1-C6 alkyl group, a C1-C6 alkylsulfonyl group, (C1-C6 alkyl)carbonyl group, a (C1-C6 alkoxy)carbonyl group, a (C1-C6 alkylamino)carbonyl group, a di(C1-C6 alkyl)aminocarbonyl group, a (C3-C6 cycloalkylamino)carbonyl group, a phenyl group, a benzyl group, or phenylsulfonyl group;
- wherein the C1-C6 alkyl group, the (C1-C6 alkoxy)C1-C6 alkyl group, the C2-C6 alkenyl group, the C2-C6 alkynyl group, the C3-C6 cycloalkyl group, the (C1-C6 alkylthio)C1-C6 alkyl group, the C1-C6 alkylsulfonyl group, the (C1-C6 alkyl)carbonyl group, and the (C1-C6 alkoxy)carbonyl group may be optionally substituted with one or more halogens, provided that when they are substituted with two or more halogens, then the halogens may be same or different;
- and
- the phenyl group, the benzyl group, and the phenylsulfonyl group may optionally have one or more substituents selected from Group 3, provided that when they have two or more substituents, then the substituents may be same or different;
- the Group 3 consists of halogen, a C1-C6 alkyl group, a C1-C6 alkoxy group, and a (C1-C6 alkoxy)C1-C6 alkyl group;
- in the Group 3, the C1-C6 alkyl group, the C1-C6 alkoxy group, and the (C1-C6 alkoxy)C1-C6 alkyl group may be optionally substituted with one or more halogens, provided that when they are substituted with two or more halogens, then the halogens may be same or different;
- R5 represents a C1-C6 alkyl group or a phenyl group;
- wherein the C1-C6 alkyl group may be optionally substituted with one or more halogens, provided that when it is substituted with two or more halogens, then the halogens may be same or different;
- and
- the phenyl group may optionally have one or more substituents selected from Group 5, provided that when it has two or more substituents, then the substituents may be same or different;
- the Group 5 consists of halogen, a C1-C6 alkyl group, and a C1-C6 alkoxy group;
- in the Group 5, the C1-C6 alkyl group and the C1-C6 alkoxy group may be optionally substituted with one or more halogens, provided that when they are substituted with two or more halogens, then the halogens may be same or different;
- G represents a C6-C10 aryl group, a 5-6-membered heteroaryl group, or an 8- to 10-membered fused heteroaryl group;
- wherein the C6-C10 aryl group, the 5- or 6-membered heteroaryl group, and the 8- to 10-membered fused heteroaryl group may optionally have one or more substituents selected from Group R4, provided that when they have two or more substituents, then the substituents may be same or different;
- the Group R4 consists of halogen, a cyano group, a nitro group, a formyl group, a C1-C6 alkyl group, a C1-C6 alkoxy group, a (C1-C6 alkoxy)C1-C6 alkyl group, a C2-C6 alkenyl group, a C2-C6 alkynyl group, a C3-C6 cycloalkyl group, a C1-C6 alkylthio group, a C1-C6 alkylsulfinyl group, a C1-C6 alkylsulfonyl group, a C1-C6 alkylamino group, a di(C1-C6 alkyl)amino group, a C3-C6 cycloalkylamino group, a (C1-C6 alkyl)carbonyl group, a (C3-C6 cycloalkyl)carbonyl group, a (C1-C6 alkoxy)carbonyl group, a (C1-C6 alkylamino)carbonyl group, a di(C1-C6 alkyl)aminocarbonyl group, a (C3-C6 cycloalkylamino)carbonyl group, a tri(C1-C6 alkyl)silyl group, a C6-C10 aryl group, and a 5- or 6-membered heteroaryl group;
- in the Group R4, the C1-C6 alkyl group, the C1-C6 alkoxy group, the (C1-C6 alkoxy)C1-C6 alkyl group, the C2-C6 alkenyl group, the C2-C6 alkynyl group, the C3-C6 cycloalkyl group, the C1-C6 alkylthio group, the C1-C6 alkylsulfinyl group, the C1-C6 alkylsulfonyl group, the (C1-(6 alkyl)carbonyl group, the (C3-C6 cycloalkyl)carbonyl group, and the (C1-C6 alkoxy)carbonyl group may be optionally substituted with one or more halogens, provided that when they are substituted with two or more halogens, then the halogens may be same or different;
- and
- the C6-C10 aryl group and the 5- or 6-membered heteroaryl group may optionally have one or more substituents selected from Group 4, provided that when they have two or more substituents, then the substituents may be same or different;
- the Group 4 consists of halogen, a cyano group, a nitro group, a formyl group, a C1-C6 alkyl group, a C1-C6 alkoxy group, a (C1-C6 alkoxy)C1-C6 alkyl group, a C2-C6 alkenyl group, a C2-C6 alkynyl group, a C3-C6 cycloalkyl group, a C1-C6 alkylthio group, a C1-C6 alkylsulfinyl group, a C1-C6 alkylsulfonyl group, a C1-C6 alkylamino group, a di(C1-C6 alkylamino group, a C3-C6 cycloalkylamino group, a (C1-C6 alkyl)carbonyl group, a (C3-C6 cycloalkyl)carbonyl group, a (C1-C6 alkoxy)carbonyl group, a (C1-C6 alkylamino)carbonyl group, a di(C1-C6 alkyl)aminocarbonyl group, a (C3-C6 cycloalkylamino)carbonyl group, and a tri(C1-C6 alkyl)silyl group;
- in the Group 4, the C1-C6 alkyl group, the C1-C6 alkoxy group, the (C1-C6 alkoxy)C1-C6 alkyl group, the C2-C6 alkenyl group, the C2-C6 alkynyl group, the C3-C6 cycloalkyl group, the C1-C6 alkylthio group, the C1-C6 alkylsulfinyl group, the C1-C6 alkylsulfonyl group, the (C1-C6 alkyl)carbonyl group, the (C3-C6 cycloalkyl)carbonyl group, and the C1-C6 alkoxy)carbonyl group may be optionally substituted with one or more halogens, provided, that when they are substituted with two or more halogens, then the halogens may be same or different;
- n represents an integer of 0, 1 or 2;
- V represents 1 or 2;
- and
- M represents an alkali metal when V is an integer of 1, and M represents an alkali earth metal when V is an integer of 2.
A method for producing a compound of the formula (1):
- which comprises the steps of
- reacting a compound of the formula (4):
- with a base to obtain a compound of the formula (2):
- and
- reacting the compound of the formula (2) with a compound of the formula (3):
- M(OR1)v (3);
- wherein the symbols in the formulae (1), (2), (3) and (4) are defined as follows:
- R1 represents hydrogen, a C1-C6 alkyl group, or a phenyl group;
- wherein the C1-C6 alkyl group may be optionally substituted with one or more halogens, provided that when it is substituted with two or more halogens, then the halogens may be same or different;
- and
- the phenyl group may optionally have one or more substituents selected from Group 1, provided that when they have two or more substituents, then the substituents may be same or different;
- the Group 1 consists of halogen, a cyano group, a nitro group, a C1-C6 alkyl group, a C1-C6 alkoxy group, and a (C1-C6 alkoxy)C1-C6 alkyl group;
- in the Group 1, the C1-C6 alkyl group, the C1-C6 alkoxy group, and the (C1-C6 alkoxy)C1-C6 alkyl group may be optionally substituted with one or more halogens, provided that when they are substituted with two or more halogens, then the halogens may be same or different;
- R2 represents hydrogen, a C1-C6 alkyl group, a (C1-C6 alkoxy)C1-C6 alkyl group, a C2-C6 alkenyl group, a C2-C6 alkynyl group, a C3-C6 cycloalkyl group, a (C1-C6 alkylthio)C1-C6 alkyl group, a (C1-C6 alkylsulfinyl)C1-C6 alkyl group, a (C1-C6 alkylsulfonyl)C1-C6 alkyl group, a phenyl group, or a 5- or 6-membered heteroaryl group;
- wherein the C1-C6 alkyl group, the (C1-C6 alkoxy)C1-C6 alkyl group, the C2-C6 alkenyl group, the C2-C6 alkynyl group, the C3-C6 cycloalkyl group, the (C1-C6 alkylthio)C1-C6 alkyl group, the (C1-C6 alkylsulfinyl)C1-C6 alkyl group, and the (C1-C6 alkylsulfonyl)C1-C6 alkyl group may be optionally substituted with one or more halogens, provided that when they are substituted with two or more halogens, then the halogens may be same or different;
- and the phenyl group and the 5- or 6-membered heteroaryl group may optionally have one or more substituents selected from Group 2, provided that when they have two or more substituents, then the substituents may be same or different;
- the Group 2 consists of halogen, a cyano group, as nitro group, a formyl group, a C1-C6 alkyl group, a C1-C6 alkoxy group, a (C1-C6 alkoxy)C1-C6 alkyl group, a C2-C6 alkenyl group, a C2-C6 alkynyl group, a C3-C6 cycloalkyl group, a C1-C6 alkylthio group, a C1-C6 alkylsulfinyl group, a C1-C6 alkylsulfonyl group, a C1-C6 alkylamino group, a di(C1-C6 alkyl)amino group, a C3-C6 cycloalkylamino group, a (C1-C6 alkyl)carbonyl group, a (C3-C6 cycloalkyl)carbonyl group, a (C1-C6 alkoxy)carbonyl group, a (C1-C6 alkylamino)carbonyl group, a di(C1-C6 alkyl)aminocarbonyl group, a (C3-C6 cycloalkylamino)carbonyl group, and a tri(C1-C6 alkyl)silyl group;
- in the Group 2, the C1-C6 alkyl group, the C1-C6 alkoxy group, the (C1-C6 alkoxy)C1-C6 alkyl group, the C2-C6 alkenyl group, the C2-C6 alkynyl group, the C3-C6 cycloalkyl group, the C1-C6 alkylthio group, the C1-C6 alkylsulfinyl group, the C1-C6 alkylsulfonyl group, the (C1-C6 alkyl)carbonyl group, the (C3-C6 cycloalkyl)carbonyl group, and the (C1-C6 alkoxy)carbonyl group may be optionally substituted with one or more halogens, provided, that when they are substituted with two or more halogens, then the halogens may be same or different,
- R3 represents hydrogen, a C1-C6 alkyl group, a (C1-C6 alkoxy)C1-C6 alkyl group, a C2-C6 alkenyl group, a C2-C6 alkynyl group, a C3-C6 cycloalkyl group, a (C1-C6 alkylthio)C1-C6 alkyl group, a C1-C6 alkylsulfonyl group, a (C1-C6 alkyl)carbonyl group, a (C1-C6 alkoxy)carbonyl group, a (C1-C6 alkylamino)carbonyl group, a di(C1-C6 alkyl)aminocarbonyl group, a (C3-C6 cycloalkylamino)carbonyl group, a phenyl group, a benzyl group, or a phenylsulfonyl group;
- wherein the C1-C6 alkyl group, the (C1-C6 alkoxy)C1-C6 alkyl group, the C2-C6 alkenyl group, the C2-C6 alkynyl group, the C3-C6 cycloalkyl group, the (C1-C6 alkylthio)C1-C6 alkyl group, the C1-C6 alkylsulfonyl group, the (C1-C6 alkyl)carbonyl group, and the (C 1 (6 alkoxy)carbonyl group may be optionally substituted with one or more halogens, provided that when they are substituted with two or more halogens, then the halogens may be same or different;
- and the phenyl group, the benzyl group, and the phenylsulfonyl group may optionally have one or more substituents selected from Group 3, provided that when they have two or more substituents, then the substituents may be same or different;
- the Group 3 consists of halogen, a C1-C6 alkyl group, a C1-C6 alkoxy group, and a (C1-C6 alkoxy)C1-C6 alkyl group;
- in the Group 3, the C1-C6 alkyl group, the C1-C6 alkoxy group, and the (C1-C6 alkoxy)C1-C6 alkyl group may be optionally substituted with one or more halogens, provided that when they are substituted with two or more halogens, then the halogens may be same or different;
- R5 represents a C1-C6 alkyl group or a phenyl group;
- wherein the C1-C6 alkyl group may be optionally substituted with one or more halogens, provided that when it is substituted with two or more halogens, then the halogens may be same or different;
- and the phenyl group may optionally have one or more substituents selected from Group 5, provided that when it has two or more substituents, then the substituents may be same or different;
- the Group 5 consists of halogen, a C1-C6 alkyl group, and a C1-C6 alkoxy group;
- in the Group 5, the C1-C6 alkyl group and the C1-C6 alkoxy group may be optionally substituted with one or more halogens, provided that when they are substituted with two or more halogens, then the halogens may be same or different;
- G represents a C6-C10 aryl group, a 5- or 6-membered heteroaryl group, or an 8- to 10-membered fused heteroaryl group;
- wherein the C6-C10 aryl group, the 5- or 5-membered heteroaryl group, and the 8- to 10-membered fused heteroaryl group may optionally have one or more substituents selected from Group R4, provided that when they have two or more substituents, then the substituents may be same or different;
- the Group R4 consists of halogen, a cyano group, a nitro group, a formyl group, a C1-C6 alkyl group, a C1-C6 alkoxy group, a (C1-C6 alkoxy)C1-C6 alkyl group, a C2-C6 alkenyl group, a C2-C6 alkynyl group, a C3-C6 cycloalkyl group, a C1-C6 alkylthio group, a C1-C6 alkylsulfinyl group;
- a C1-C6 all group, a C1-C6 alkylamino group, a di(C1-C6 alkyl)amino group, a C3-C6 cycloalkylamino group, a (C1-C6 alkyl)carbonyl group, a (C3-C6 cycloalkyl)carbonyl group, a (C1-C6 alkoxy)carbonyl group, a (C1-C6 alkylamino)carbonyl group, a di(C1-C6 alkyl)aminocarbonyl group, a (C3-C6 cycloalkylamino)carbonyl group, a tri(C1-C6 alkyl)silyl group, a C6-C10 aryl group, and a 5- or 6-membered heteroaryl group;
- in the Group R4, the C1-C6 alkyl group, the C1-C6 alkoxy group, the (C1-C6 alkoxy)C1-C6 alkyl group, the C2-C6 alkenyl group, the C2-C6 alkynyl group, the C3-C6 cycloalkyl group, the C1-C6 alkylthio group, the C1-C6 alkylsulfinyl group, the C1-C6 alkylsulfonyl group, the (C1-C6 alkyl)carbonyl group, the (C3-C6 cycloalkyl)carbonyl group, and the (C1-C6 alkoxy)carbonyl group may be optionally substituted with one or more halogens, provided that when they are substituted with two or more halogens, then the halogens may be same or different;
- and the C6-C10 aryl group and the 5- or 6-membered heteroaryl group may optionally have one or more substituents selected from Group 4, provided that when they have two or more substituents, then the substituents may be same or different;
- the Group 4 consists of halogen, a cyano group, a nitro group, a formyl group, a C1-C6 alkyl group, a C1-C6 alkoxy group, a (C1-C6 alkoxy)C1-C6 alkyl group, a C2-C6 alkenyl group, a C2-C6 alkynyl group, a C3-C6 cycloalkyl group, a C1-C6 alkylthio group, a C1-C6 alkylsulfinyl group, a C1-C6 alkylsulfonyl group, a C1-C6 alkylamino group, a di(C1-C6 alkyl)amino group, a C3-C6 cycloalkylamino group, a (C1-C6 alkyl)carbonyl group, a (C3-C6 cycloalkyl)carbonyl group, a (C1-C6 alkoxy)carbonyl group, a (C1-C6 alkylamino)carbonyl group, a di(C1-C6 alkyl)aminocarbonyl group, a (C3-C6 cycloalkylamino)carbonyl group, and a tri(C1-C6 alkyl)silyl group;
- in the Group 4, the C1-C6 alkyl group, the C1-C6 alkoxy group, the (C1-C6 alkoxy)C1-C6 alkyl group, the C2-C6 alkenyl group, the C2-C6 alkynyl group, the C3-C6 cycloalkyl group, the C1-C6 alkylthio group, the C1-C6 alkylsulfinyl group, the C1-C6 alkylsulfonyl group, the (C1-C6 alkyl)carbonyl group, the (C3-C6 cycloalkyl)carbonyl group, and the (C1-C6 alkoxy)carbonyl group may be optionally substituted with one or more halogens, provided that when they are substituted with two or more halogens, then the halogens may be same or different;
- n represents an integer of 0, 1 or 2;
- V represents an integer of 1 or 2;
- and
- M represents an alkali metal when V is an integer of 1, and M represents an alkali earth metal when V is an integer of 2.
A method for producing a compound of the formula (2):
- which comprises reacting a compound of the formula (4):
- with a base;
- wherein the symbols in the formulae (2) and (4) are defined as follows:
- R2 represents hydrogen, a C1-C6 alkyl group, a (C1-C6 alkoxy)C1-C6 alkyl group, a C2-C6 alkenyl group, a C2-C6 alkynyl group, a C3-C6 cycloalkyl group, a (C1-C6 alkylthio)C1-C6 alkyl group, a (C1-C6 alkylsulfinyl)C1-C6 alkyl group, a (C1-C6 alkylsulfonyl)C1-C6 alkyl group, a phenyl group, or a 5- or 6-membered heteroaryl group;
- wherein the C1-C6 alkyl group, the (C1-C6 alkoxy)C1-C6 alkyl group, the C2-C6 alkenyl group, the C2-C6 alkynyl group, the C3-C6 cycloalkyl group, the (C1-C6 alkylthio)C1-C6 alkyl group, the (C1-C6 alkylsulfinyl)C1-C6 alkyl group, and the (C1-C6 alkylsulfonyl)C1-C6 alkyl group may be optionally substituted with one or more halogens, provided that when they are substituted with two or more halogens, then the halogens may be same or different;
- and
- the phenyl group and the 5- or 6-membered heteroaryl group may optionally have one or more substituents selected from Group 2, provided that when they have two or more substituents, then the substituents may be same or different;
- the Group 2 consists of halogen, a cyano group, a nitro group, a formyl group, a C1-C6 alkyl group, a C1-C6 alkoxy group, a (C1-C6 alkoxy)C1-C6 alkyl group, a C2-C6 alkenyl group, a C2-C6 alkynyl group, a C3-C6 cycloalkyl group, a C1-C6 alkylthio group, a C1-C6 alkylsulfinyl group, a C1-C6 alkylsulfonyl group, a C1-C6 alkylamino group, a di(C1-C6 alkyl)amino group, a C3-C6 cycloalkylamino group, a (C1-C6 alkyl)carbonyl group, a (C3-C6 cycloalkyl)carbonyl group, a (C1-C6 alkoxy)carbonyl group, a (C1-C6 alkylamino)carbonyl group, a di(C1-C6 alkyl)aminocarbonyl group, a (C3-C6 cycloalkylamino)carbonyl group, and a tri(C1-C6 alkyl)silyl group;
- in the Group 2, the C1-C6 alkyl group, the C1-C6 alkoxy group, the (C1-C6 alkoxy)C1-C6 alkyl group, the C2-C6 alkenyl group, the C2-C6 alkynyl group, the C3-C6 cycloalkyl group, the C1-C6 alkylthio group, the C1-C6 alkylsulfinyl group, the C1-C6 alkylsulfonyl group, the (C1-C6 alkyl)carbonyl group, the (C3-C6 cycloalkyl)carbonyl group, and the (C1-C6 alkoxy)carbonyl group may be optionally substituted with one or more halogens, provided that when they are substituted with two or more halogens, then the halogens may be same or different;
- R3 represents hydrogen, a C1-C6 alkyl group, a C1-C6 alkoxy)C1-C6 alkyl group, a C2-C6 alkenyl group, a C2-C6 alkyl group, a C3-C6 cycloalkyl group, a (C1-C6 alkylthio)C1-C6 alkyl group, a C1-C6 alkylsulfonyl group, a (C1-C6 alkyl)carbonyl group, a (C1-C6 alkoxy)carbonyl group, a (C1-C6 alkylamino)carbonyl group, a di(C1-C6 alkyl)aminocarbonyl group, a (C3-C6 cycloalkylamino)carbonyl group, a phenyl group, a benzyl group, or a phenylsulfonyl group;
- wherein the C1-C6 alkyl group, the (C1-C6 alkoxy)C1-C6 alkyl group, the C2-C6 alkenyl group, the C2-C6 alkynyl group, the C3-C6 cycloalkyl group, the (C1-C6 alkylthio)C1-C6 alkyl group, the C1-C6 alkylsulfonyl group, the (C1-C6 alkyl)carbonyl group, and the (C1-C6 alkoxy)carbonyl group may be optionally substituted with one or more halogens, provided that when they are substituted with two or more halogens, then the halogens may be same or different and the phenyl group, the benzyl group, and the phenylsulfonyl group may optionally have one or more substituents selected from Group 3, provided that when they have two or more substituents, then the substituents may be same or different;
- the Group 3 consists of halogen a C1-C6 alkyl group, a C1-C6 alkoxy group, and a (C1-C6 alkoxy)C1-C6 alkyl group;
- in the Group 3, the C1-C6 alkyl group, the C1-C6 alkoxy group, and the (C1-C6 alkoxy)C1-C6 alkyl group may be optionally substituted with one or more halogens, provided that when they are substituted with two or more halogens, then the halogens may be same or different;
- R5 represents a C1-C6 alkyl group or a phenyl group;
- wherein the C1-C6 alkyl group may be optionally substituted with one or more halogens, provided that when it is substituted with two or more halogens, then the halogens may be same or different;
- and the phenyl group may optionally have one or more substituents selected from Group 5, provided that when it has two or more substituents, then the substituents may be same or different;
- the Group 5 consists of halogen, a C1-C6 alkyl group, and a C1-C6 alkoxy group;
- in the Group 5, the C1-C6 alkyl group and the C1-C6 alkoxy group may be optionally substituted with one or more halogens, provided that when they are substituted with two or more halogens;
- then the halogens may be same or different;
- G represents a C6-C10 an group, a 5- or 6-membered heteroaryl group, or an 8- to 10-membered fused heteroaryl group;
- wherein the C6-C10 aryl group, the 5- or 6-membered heteroaryl group, and the 8- to 10-membered fused heteroaryl group may optionally have one or more substituents selected from Group R4, provided that when they have two or more substituents, then the substituents may be same or different;
- the Group R4 consists of halogen, as cyano group, a nitro group, a formyl group, a C1-C6 alkyl group, a C1-C6 alkoxy group, a (C1-C6 alkoxy)C1-C6 alkyl group, a C2-C6 alkenyl group, a C2-C6 alkynyl group, a C3-C6 cycloalkyl group, a C1-C6 alkylthio group, a C1-C6 alkylsulfinyl group, a C1-C6 alkylsulfonyl group, a C1-C6 alkylamino group, a di(C1-C6 alkyl)amino group, a C3-C6 cycloalkylamino group, a (C1-C6 alkyl)carbonyl group, a (C3-C6 cycloalkyl)carbonyl group, a (C1-C6 alkoxy)carbonyl group, a (C1-C6 alkylamino)carbonyl group, a di(C1-C6 alkyl)aminocarbonyl group, a (C3-C6 cycloalkylamino)carbonyl group, a tri(C1-C6 alkyl)silyl group, a C6-C10 aryl group, and a 5- or 6-membered heteroaryl group;
- in the Group R4, the C1-C6 alkyl group, the C1-C6 alkoxy group, the (C1-C6 alkoxy)C1-C6 alkyl group, the C2-C6 alkenyl group, the C2-C6 alkynyl group, the C3-C6 cycloalkyl group, the C1-C6 alkylthio group, the C1-C6 alkylsulfinyl group, the C1-C6 alkylsulfonyl group, the (C1-C6 alkyl)carbonyl group, the (C3-C6 cycloalkyl)carbonyl group, and the (C1-C6 alkoxy)carbonyl group may be optionally substituted with one or more halogens, provided that when they are substituted with two or more halogens, then the halogens may be same or different;
- and the C6-C10 aryl group and the 5- or 6-membered heteroaryl group may optionally have one or more substituents selected from Group 4, provided that when they have two or more substituents, then the substituents may be same or different;
- the Group 4 consists of halogen, a cyano group, a nitro group, a formyl group, a C1-C6 alkyl group, a C1-C6 alkoxy group, a (C1-C6 alkoxy)C1-C6 alkyl group, a C2-C6 alkenyl group, a C2-C6 alkynyl group, a C3-C6 cycloalkyl group, a C1-C6 alkylthio group, a C1-C6 alkylsulfinyl group, a C1-C6 alkylsulfonyl group, a C1-C6 alkylamino group, a di(C1-C6 alkyl)amino group, a C3-C6 cycloalkylamino group, a (C1-C6 alkyl)carbonyl group, a (C3-C6 cycloalkyl)carbonyl group, a (C1-C6 alkoxy)carbonyl group, a (C1-C6 alkylamino)carbonyl group, a di(C1-C6 alkyl)aminocarbonyl group, a (C3-C6 cycloalkylamino)carbonyl group, and a tri(C1-C6 alkyl)silyl group;
- in the Group 4, the C1-C6 alkyl group, the C1-C6 alkoxy group, the (C1-C6 alkoxy)C1-C6 alkyl group, the C2-C6 alkenyl group, the C2-C6 alkynyl group, the C3-C6 cycloalkyl group, the C1-C6 alkylthio group, the C1-C6 alkylsulfinyl group, the C1-C6 alkylsulfonyl group, the (C1-C6 alkyl)carbonyl group, the (C3-C6 cycloalkyl)carbonyl group, and the (C1-C6 alkoxy)carbonyl group may be optionally substituted with one or more halogens, provided that when they are substituted with two or more halogens, then the halogens may be same or different;
- and
- n represents an integer of 0, 1 or 2.
A method for producing a compound of the formula (1):
- which comprises the steps of:
- reacting a compound of the formula (5):
- with a compound of the formula (6):
- to obtain a compound of the formula (4):
- reacting the compound of the formula (4) with a base to obtain a compound of the formula (2):
- and
- reacting the compound of the formula (2) with a compound of the formula (3):
- M(OR1)v (3);
- wherein the symbols in the formulae (1), (2), (3), (4), (5) and (6) are defined as follows:
- R1 represents hydrogen, a C1-C6 alkyl group, or a phenyl group;
- wherein the C1-C6 alkyl group may be optionally substituted with one or more halogens, provided that when it is substituted with two or more halogens, then the halogens may be same or different;
- and
- the phenyl group may optionally have one or more substituents selected from Group 1, provided that when it has two or more substituents, then the substituents may be same or different;
- the Group 1 consists of halogen, a cyano group, a nitro group, a C1-C6 alkyl group, a C1-C6 alkoxy group, and a (C1-C6 alkoxy)C1-C6 alkyl group;
- in the Group 1, the C1-C6 alkyl group, the C1-C6 alkoxy group and the (C1-C6 alkoxy)C1-C6 alkyl group may be optionally substituted with one or more halogens, provided that when they are substituted with two or more halogens, then the halogens may be same or different;
- R2 represents hydrogen, a C1-C6 alkyl group, a (C1-C6 alkoxy)C1-C6 alkyl group, a C2-C6 alkenyl group, a C2-C6 alkynyl group, a C3-C6 cycloalkyl group, a (C1-C6 alkylthio)C1-C6 alkyl group, a (C1-C6 alkylsulfinyl)C1-C6 alkyl group, a (C1-C6 alkylsulfonyl)C1-C6 alkyl group, a phenyl group, or a 5- or 6-membered heteroaryl group;
- wherein the C1-C6 alkyl group, the (C1-C6 alkoxy)C1-C6 alkyl group, the C2-C6 alkenyl group, the C2-C6 alkynyl group, the C3-C6 cycloalkyl group, the (C1-C6 alkylthio)C1-C6 alkyl group, the (C1-C6 alkylsulfinyl)C1-C6 alkyl group, and the (C1-C6 alkylsulfonyl)C1-C6 alkyl group may be optionally substituted with one or more halogens, provided that when they are substituted with two or more halogens, then the halogens may be same or different;
- and the phenyl group and the 5- or 6-membered heteroaryl group may optionally have one or more substituents selected from Group 2, provided that when they have two or more substituents, then the substituents may be same or different;
- the Group 2 consists of halogen, a cyano group, a nitro group, a formyl group, a C1-C6 alkyl group, a C1-C6 alkoxy group, a (C1-C6 alkoxy)C1-C6 alkyl group, a C2-C6 alkenyl group, a C2-C6 alkynyl group, a C3-C6 cycloalkyl group, a C1-C6 alkylthio group, a C1-C6 alkylsulfinyl group, a C1-C6 alkylsulfonyl group, a C1-C6 alkylamino group, a di(C1-C6 alkyl)amino group, a C3-C6 cycloalkylamino group, a (C1-C6 alkyl)carbonyl group, a (C3-C6 cycloakyl)carbonyl group, a (C1-C6 alkoxy)carbonyl group, a (C1-C6 alkylamino)carbonyl group, a di(C1-C6 alkyl)aminocarbonyl group, a (C3-C6 cycloalkylaminocarbonyl group, and a tri(C1-C6 alkyl)silyl group;
- in the Group 2, the C1-C6 alkyl group, the C1-C6 alkoxy group, the (C1-C6 alkoxy)C1-C6 alkyl group, the C2-C6 alkenyl group, the C2-C6 alkynyl group, the C3-C6 cycloalkyl group, the C1-C6 alkylthio group, the C1-C6 alkylsulfinyl group, the C1-C6 alkylsulfonyl group, the (C1-C6 alkyl)carbonyl group, the (C3-C6 cycloalkyl)carbonyl group, and the (C1-C6 alkoxy)carbonyl group may be optionally substituted with one or more halogens, provided that when they are substituted with two or more halogens, then the halogens may be same or different;
- R3 represents hydrogen, a C1-C6 alkyl group, a (C1-C6 alkoxy)C1-C6 alkyl group, a C2-C6 alkenyl group, a C2-C6 alkynyl group, a C3-C6 cycloalkyl group, a (C1-C6 alkylthio)C1-C6 alkyl group, a C1-C6 alkylsulfonyl group, a (C1-C6 alkyl)carbonyl group, a (C1-C6 alkoxy)carbonyl group, a (C1-C6 alkylamino)carbonyl group, a di(C1-C6 alkyl)aminocarbonyl group, a (C3-C6 cycloalkylamino)carbonyl group, a phenyl group, a benzyl group, or a phenylsulfonyl group;
- wherein the C1-C6 alkyl group, the (C1-C6 alkoxy)C1-C6 alkyl group, the C2-C6 alkenyl group, the C2-C6 alkynyl group, the C3-C6 cycloalkyl group, the (C1-C6 alkylthio)C1-C6 alkyl group, the C1-C6 alkylsulfonyl group, the (C1-C6 alkyl)carbonyl group, and the (C1-C6 alkoxy)carbonyl group may be optionally substituted with one or more halogens, provided that when they are substituted with two or more halogens, then the halogens may be same or different;
- and the phenyl group, the benzyl group, and the phenylsulfonyl group may optionally have one or more substituents selected from Group 3, provided that when they have two or more substituents, then the substituents may be same or different;
- the Group 3 consists of halogen, a C1-C6 alkyl group, a C1-C6 alkoxy group, and a (C1-C6 alkoxy)C1-C6 alkyl group;
- in the Group 3, the C1-C6 alkyl group, the C1-C6 alkoxy group, and the (C1-C6 alkoxy)C1-C6 alkyl group may be optionally substituted with one or more halogens, provided that when they are substituted with two or more halogens, then the halogens may be same or different;
- R5 represents a C1-C6 alkyl group or a phenyl group;
- wherein the C1-C6 alkyl group may be optionally substituted with one or more halogens, provided that when it is substituted with two or more halogens, then the halogens may be same or different, and
- the phenyl group may optionally have one or more substituents selected from Group 5, provided that when it has two or more substituents, then the substituents may be same or different;
- the Group 5 consists of halogen, a C1-C6 alkyl group, and a C1-C6 alkoxy group;
- in the Group 5, the C1-C6 alkyl group and the C1-C6 alkoxy group may be optionally substituted with one or more halogens, provided that when they are substituted with two or more halogens, then the halogens may be same or different;
- G represents a C6-C10 aryl group, a 5- or 6-membered heteroaryl group, or an 8- to C10-membered fused heteroaryl group;
- wherein the C6-C10 aryl group, the 5- or 6-membered heteroaryl group, and the 8- to 10-membered fused heteroaryl group may optionally have one or more substituents selected from Group R4, provided that when they have two or more substituents, then the substituents may be same or different;
- the Group R4 consists of halogen, a cyano group, a nitro group, a formyl group, a C1-C6 alkyl group, a C1-C6 alkoxy group, a (C1-C6 alkoxy)C1-C6 alkyl group, a C2-C6 alkenyl group, a C2-C6 alkynyl group, a C3-C6 cycloalkyl group, a C1-C6 alkylthio group, a C1-C6 alkylsulfinyl group, a C1-C6 alkylsulfonyl group, a C1-C6 alkylamino group, a di(C1-C6 alkyl)amino group, a C3-C6 cycloalkylamino group, a (C1-C6 alkyl)carbonyl group, a (C3-C6 cycloalkyl)carbonyl group, a (C1-C6 alkoxy)carbonyl group, a (C1-C6 alkylamino)carbonyl group, a di(C1-C6 alkyl)aminocarbonyl group, a (C3-C6 cycloalkylamino)carbonyl group, a tri(C1-C6 alkyl)silyl group, a C6-C10 aryl group, and a 5- or 6-membered heteroaryl group;
- in the Group R4, the C1-C6 alkyl group, the C1-C6 alkoxy group, the (C1-C6 alkoxy)C1-C6 alkyl group, the C2-C6 alkenyl group, the C2-C6 alkynyl group, the C3-C6 cycloalkyl group, the C1-C6 alkylthio group, the C1-C6 alkylsulfinyl group, the C1-C6 alkylsulfonyl group, the (C1-C6 alkyl)carbonyl group, the (C3-C6 cycloalkyl)carbonyl group, and the (C1-C6 alkoxy)carbonyl group may be optionally substituted with one or more halogens, provided that when they are substituted with two or more halogens, then the halogens may be same or different;
- and the C6-C10 aryl group and the 5- or 6-membered heteroaryl group may optionally have one or more substituents selected from Group 4, provided that when they have two or more substituents, then the substituents may be same or different;
- the Group 4 consists of halogen, a cyano group, a nitro group, a formyl group, a C1-C6 alkyl group, a C1-C6 alkoxy group, a (C1-C6 alkoxy)C1-C6 alkyl group, a C2-C6 alkenyl group, a C2-C6 alkynyl group, a C3-C6 cycloalkyl group, a C1-C6 alkylthio group, a C1-C6 alkylsulfinyl group, a C1-C6 alkylsulfonyl group, a C1-C6 alkylamino group, a di(C1-C6 alkyl)amino group, a C3-C6 cycloalkylamino group, a (C1-C6 alkyl)carbonyl group, a (C3-C6 cycloalkyl)carbonyl group, a (C1-C6 alkoxy)carbonyl group, a (C1-C6 alkylamino)carbonyl group, a di(C1-C6 alkyl)aminocarbonyl group, a (C3-C6 cycloalkylamino)carbonyl group, and a tri(C1-C6 alkyl)silyl group;
- in the Group 4, the C1-C6 alkyl group, the C1-C6 alkoxy group, the (C1-C6 alkoxy)C1-C6 alkyl group, the C2-C6 alkenyl group, the C2-C6 alkynyl group, the C3-C6 cycloalkyl group, the C1-C6 alkylthio group, the C1-C6 alkylsulfinyl group, the C1-C6 alkylsulfonyl group, the (C1-C6 alkyl)carbonyl group, the (C3-C6 cycloalkyl)carbonyl group, and the (C1-C6 alkoxy)carbonyl group may be optionally substituted with one or more halogens, provided that when they are substituted with two or more halogens, then the halogens may be same or different;
- n represents an integer of 0, 1 or 2;
- V represents an integer of 1 or 2;
- M represents an alkali metal when V is an integer of 1, and M represents an alkali earth metal when V is an integer of 2;
- and
- X1 represents fluorine, chlorine, bromine, or iodine.
A method for producing a compound of the formula (4):
- which comprises reacting a compound of the formula (5):
- with a compound of the formula (6):
- wherein the symbols in the formulae (4), (5) and (6) are defined as follows:
- R2 represents hydrogen, a C1-C6 alkyl group, a (C1-C6 alkoxy)C1-C6 alkyl group, a C2-C6 alkenyl group, a C2-C6 alkynyl group, a C3-C6 cycloalkyl group, a (C1-C6 alkylthio)C1-C6 alkyl group, a (C1-C6 alkylsulfinyl)C1-C6 alkyl group, as (C1-C6 alkylsulfonyl)C1-C6 alkyl group, a phenyl group, or a 5- or 6-membered heteroaryl group;
- wherein the C1-C6 alkyl group, the (C1-C6 alkoxy)C1-C6 alkyl group, the C2-C6 alkenyl group, the C2-C6 alkynyl group, the C3-C6 cycloalkyl group, the (C1-C6 alkylthio)C1-C6 alkyl group, the (C1-C6 alkylsulfinyl)C1-C6 alkyl group, and the (C1-C6 alkylsulfonyl)C1-C6 alkyl group may be optionally substituted with one or more halogens, provided that when they are substituted with two or more halogens, then the halogens may be same or different, and
- the phenyl group and 5- or 6-membered heteroaryl group may optionally have one or more substituents selected from Group 2, provided that when they have two or more substituents, then the substituents may be same or different;
- the Group 2 consists of halogen, a cyano group, a intro group, a formyl group, a C1-C6 alkyl group, a C1-C6 alkoxy group, a (C1-C6 alkoxy)C1-C6 alkyl group, to C2-C6 alkenyl group, a C2-C6 alkynyl group, a C3-C6 cycloalkyl group, a C1-C6 alkylthio group, a C1-C6 alkylsulfinyl group, a C1-C6 alkylsulfonyl group, a C1-C6 alkylamino group, a di(C1-C6 alkyl)amino group, a C3-C6 cycloalkylamino group, a (C1-C6 alkyl)carbonyl group, a (C3-C6 cycloalkyl)carbonyl group, a (C1-C6 alkoxy)carbonyl group, a (C1-C6 alkylamino)carbonyl group, a di(C1-C6 alkyl)aminocarbonyl group, a (C3-C6 cycloalkylamino)carbonyl group, and a tri(C1-C6 alkyl)silyl group;
- in the Group 2, the C1-C6 alkyl group, the C1-C6 alkoxy group, the (C1-C6 alkoxy)C1-C6 alkyl group, the C2-C6 alkenyl group, the C2-C6 alkynyl group, the C3-C6 cycloalkyl group, the C1-C6 alkylthio group, the C1-C6 alkylsulfinyl group, the C1-C6 alkylsulfonyl group, the (C1-C6 alkyl)carbonyl group, the (C3-C6 cycloalkyl)carbonyl group, and the (C1-C6 alkoxy)carbonyl group may be optionally substituted with one or more halogens, provided that when they are substituted with two or more halogens, then the halogens may be same or different;
- R3 represents hydrogen, a C1-C6 alkyl group, a (C1-C6 alkoxy)C1-C6 alkyl group, a C2-C6 alkenyl group, a C2-C6 alkynyl group, a C3-C6 cycloalkyl group, a (C1-C6 alkylthio)C1-C6 alkyl group, a C1-C6 alkylsulfonyl group, a (C1-C6 alkyl)carbonyl group, a (C1-C6 alkoxy)carbonyl group, a (C1-C6 alkylamino)carbonyl group, a di(C1-C6 alkyl)aminocarbonyl group, a (C3-C6 cycloalkylamino)carbonyl group, a phenyl group, a benzyl group, or a phenylsulfonyl group:
- wherein the C1-C6 alkyl group, the (C1-C6 alkoxy)C1-C6 alkyl group, the C2-C6 alkenyl group, the C2-C6 alkynyl group, the C3-C6 cycloalkyl group, the (C1-C6 alkylthio)C1-C6 alkyl group, the C1-C6 alkylsulfonyl group, the (C1-C6 alkyl)carbonyl group, and the (C1-C6 alkoxy)carbonyl group may be optionally substituted with one or more halogens, provided that when they are substituted with two or more halogens, then the halogens may be same or different;
- and the phenyl group, the benzyl group, and the phenylsulfonyl group may optionally have one or more substituents selected from Group 3, provided that when they have two or more substituents, then the substituents may be same or different,
- the Group 3 consists of halogen, a C1-C6 alkyl group, a C1-C6 alkoxy group, and a (C1-C6 alkoxy)C1-C6 alkyl group;
- in the Group 3, the C1-C6 alkyl group, the C1-C6 alkoxy group, and the (C1-C6 alkoxy)C1-C6 alkyl group may be optionally substituted with one or more halogens, provided that when they are substituted with two or more halogens, then the halogens may be same or different;
- R5 represents a C1-C6 alkyl group or a phenyl group;
- wherein the C1-C6 alkyl group may be optionally substituted with one or more halogens, provided that when it is substituted with two or more halogens, then the halogens may be same or different;
- and the phenyl group may optionally have one or more substituents selected from Group 5, provided that when it has two or more substituents, then the substituents may be same or different;
- the Group 5 consists of halogen, a C1-C6 alkyl group, and a C1-C6 alkoxy group;
- in the Group 5, the C1-C6 alkyl group and the C1-C6 alkoxy group may be optionally substituted with one or more halogens, provided that when they are substituted with two or more halogens, then the halogens may be same or different;
- G represents a C6-C 10 an group, a 5- or 6-membered heteroaryl group, or an 8- to 10-membered fused heteroaryl group;
- wherein the C6-C10 aryl group, the 5- or 6-membered heteroaryl group, and the 8- to 10-membered fused heteroaryl group may optionally have one or more substituents selected from Group R4, provided that when they have two or more substituents, then the substituents may be same or different;
- the Group R4 of halogen, a cyano group, a nitro group, a formyl group, a C1-C6 alkyl group, a C1-C6 alkoxy group, a (C1-C6 alkoxy)C1-C6 alkyl group, a C2-C6 alkenyl group, a C2-C6 alkynyl group, a C3-C6 cycloalkyl group, a C1-C6 alkylthio group, a C1-C6 alkylsulfinyl group, a C1-C6 alkylsulfonyl group, a C1-C6 alkylamino group, a di(C1-C6 alkyl)amino group, a C3-C6 cycloalkylamino group, a (C1-C6 alkyl)carbonyl group, a (C3-C6 cycloalkyl)carbonyl group, a (C1-C6 alkoxy)carbonyl group, a (C1-C6 alkylamino)carbonyl group, a di(C1-C6 alkyl)aminocarbonyl group, a (C3-C6 cycloalkylamino)carbonyl group, a tri(C1-C6 alkyl)silyl group, a C6-C10 aryl group, and a 5- or 6-membered heteroaryl group;
- in the Group R4, the C1-C6 alkyl group, the C1-C6 alkoxy group, the (C1-C6 alkoxy)C1-C6 alkyl group, the C2-C6 alkenyl group, the C2-C6 alkynyl group, the C3-C6 cycloalkyl group, the C1-C6 alkylthio group, the C1-C6 alkylsulfinyl group, the C1-C6 alkylsulfonyl group, the (C1-C6 alkyl)carbonyl group, the (C3-C6 cycloalkyl)carbonyl group, and the (C1-C6 alkoxy)carbonyl group may be optionally substituted with one or more halogens, provided that when they are substituted with two or more halogens, then the halogens may be same or different;
- and the C6-C10 aryl group and the 5- or 6-membered heteroaryl group may optionally have one or more substituents selected from Group 4, provided that when they have two or more substituents, then the substituents may be same or different;
- the Group 4 consists of halogen, a cyano group, a nitro group, a formyl group, a C1-C6 alkyl group, a C1-C6 alkoxy group, a (C1-C6 alkoxy)C1-C6 alkyl group, a C2-C6 alkenyl group, a C2-C6 alkynyl group, a C3-C6 cycloalkyl group, a C1-C6 alkylthio group, a C1-C6 alkylsulfinyl group, a C1-C6 alkylsulfonyl group, a C1-C6 alkylamino group, a di(C1-C6 alkyl)amino group, a C3-C6 cycloalkylamino group, a (C1-C6 alkyl)carbonyl group, a (C3-C6 cycloalkyl)carbonyl group, a (C1-C6 alkoxy)carbonyl group, a (C1-C6 alkylamino)carbonyl group, a di(C1-C6 alkyl)aminocarbonyl group, a (C3-C6 cycloalkylamino)carbonyl group, and a tri(C1-C6 alkyl)silyl group;
- in the Group 4, the C1-C6 alkyl group, the C1-C6 alkoxy group, the (C1-C6 alkoxy)C1-C6 alkyl group, the C2-C6 alkenyl group, the C2-C6 alkynyl group, the C3-C6 cycloalkyl group, the C1-C6 alkylthio group, the C1-C6 alkylsulfinyl group, the C1-C6 alkylsulfonyl group, the (C1-C6 alkyl)carbonyl group, the (C3-C6 cycloalkyl)carbonyl group, and the (C1-C6 alkoxy)carbonyl group may be optionally substituted with one or more halogens, provided that when they are substituted with two or more halogens, then the halogens may be same or different;
- n represents an integer of 0, 1 or 2;
- and
- X1 represents fluorine, chlorine, bromine, or iodine.
A method for producing a compound of the formula (1):
- which comprises the steps of:
- reacting a compound of the formula (7):
- with a compound of the formula (12):
- to obtain a compound of the formula (4):
- reacting the compound of the formula (4) with a base to obtain a compound of the formula (2):
- and
- reacting the compound of the formula (2) with a compound of the formula (3):
- M(OR1)v (3);
- wherein the symbols in the formulae (1), (2), (3), (4), (7) and (12) are defined as follows:
- R1 represents hydrogen, a C1-C6 alkyl group or a phenyl group;
- wherein the C1-C6 alkyl group may be optionally substituted with one or more halogens, provided that when it is substituted with two or more halogens, then the halogens may be same or different;
- and the phenyl group may optionally have one or more substituents selected from Group 1, provided that when it has two or more substituents, then the substituents may be same or different;
- the Group 1 consists of halogen, a cyano group, a nitro group, a C1-C6 alkyl group, a C1-C6 alkoxy group, and a (C1-C6 alkoxy)C1-C6 alkyl group;
- in the Group 1, the C1-C6 alkyl group, the C1-C6 alkoxy group and the (C1-C6 alkoxy)C1-C6 alkyl group may be optionally substituted with one or more halogens, provided that when they are substituted with two or more halogens, then the halogens may be same or different;
- R2 represents hydrogen, a C1-C6 alkyl group, a (C1-C6 alkoxy)C1-C6 alkyl group, a C2-C6 alkenyl group, a C2-C6 alkyl group, a C3-C6 cycloalkyl group, a (C1-C6 alkylthio)C1-C6 alkyl group, a (C1-C6 alkylsulfinyl)C1-C6 alkyl group, a (C1-C6 alkylsulfonyl)C1-C6 alkyl group, a phenyl group, or a 5- or 6-membered heteroaryl group;
- wherein the C1-C6 alkyl group, the (C1-C6 alkoxy)C1-C6 alkyl group, the C2-C6 alkenyl group, the C2-C6 alkynyl group, the C3-C6 cycloalkyl group, the (C1-C6 alkylthio)C1-C6 alkyl group, the (C1-C6 alkylsulfinyl)C1-C6 alkyl group, and the (C1-C6 alkylsulfonyl)C1-C6 alkyl group may be optionally substituted with one or more halogens, provided that when they are substituted with two or more halogens, then the halogens may be same or different;
- and the phenyl group and the 5- or 6-membered heteroaryl group may optionally have one or more substituents selected from Group 2, provided that when they have two or more substituents, then the substituents may be same or different;
- the Group 2 consists of halogen, a cyano group, a nitro group, a formyl group, a C1-C6 alkyl group, a C1-C6 alkoxy group, a (C1-C6 alkoxy)C1-C6 alkyl group, a C2-C6 alkenyl group, a C2-C6 alkynyl group, a C3-C6 cycloalkyl group, a C1-C6 alkylthio group, a C1-C6 alkylsulfinyl group, a C1-C6 alkylsulfonyl group, a C1-C6 alkylamino group, a di(C1-C6 alkyl)amino group, a C3-C6 cycloalkylamino group, a (C1-C6 alkyl)carbonyl group, a (C3-C6 cycloalkyl)carbonyl group, a (C1-C6 alkoxy)carbonyl group, a (C1-C6 alkylamino)carbonyl group, a di(C1-C6 alkyl)aminocarbonyl group, a (C3-C6 cycloalkylamino)carbonyl group, and a tri(C1-C6 alkyl)silyl group;
- in the Group 2, the C1-C6 alkyl group, the C1-C6 alkoxy group, the (C1-C6 alkoxy)C1-C6 alkyl group, the C2-C6 alkenyl group, the C2-C6 alkynyl group, the C3-C6 cycloalkyl group, the C1-C6 alkylthio group, the C1-C6 alkylsulfinyl group, the C1-C6 alkylsulfonyl group, the (C1-C6 alkyl)carbonyl group, the (C3-C6 cycloalkyl)carbonyl group, and the (C1-C6 alkoxy)carbonyl group may be optionally substituted with one or more halogens, provided that when they are substituted with two or more halogens, then the halogens may be same or different;
- R3 represents hydrogen, a C1-C6 alkyl group, a (C1-C6 alkoxy)C1-C6 alkyl group, a C2-C6 alkenyl group, a C2-C6 alkynyl group, as C3-C6 cycloalkyl group, a (C1-C6 alkylthio)C1-C6 alkyl group, a C1-C6 alkylsulfonyl group, a (C1-C6 alkyl)carbonyl group, a (C1-C6 alkoxy)carbonyl group, a (C1-C6 alkylamino)carbonyl group, a di(C1-C6 alkyl)aminocarbonyl group, a (C3-C6 cycloalkylamino)carbonyl group, as phenyl group, as benzyl group, or a phenylsulfonyl group;
- wherein the C1-C6 alkyl group, the (C1-C6 alkoxy)C1-C6 alkyl group, the C2-C6 alkenyl group, the C2-C6 alkynyl group, the C3-C6 cycloalkyl group, the (C1-C6 alkylthio)C1-C6 alkyl group, the C1-C6 alkylsulfonyl group, the (C1-C6 alkyl)carbonyl group, and the (C1-C6 alkoxy)carbonyl group may be optionally substituted with one or more halogens, provided that when they are substituted with two or more halogens, then the halogens may be same or different;
- and the phenyl group, the benzyl group, and the phenylsulfonyl group may optionally have one or more substituents selected from Group 3, provided that when they have two Of more substituents, then the substituents may be same or different,
- the Group 3 consists of halogen, a C1-C6 alkyl group, a C1-C6 alkoxy group, and a (C1-C6 alkoxy)C1-C6 alkyl group;
- in the Group 3, the C1-C6 alkyl group, the C1-C6 alkoxy group, and the (C1-C6 alkoxy)C1-C6 alkyl group may be optionally substituted with one or more halogens, provided that when they are substituted with two Of more halogens, then the halogens may be same or different;
- R5 represents a C1-C6 alkyl group or a phenyl group;
- wherein the C1-C6 alkyl group may be optionally substituted with one or more halogens, provided that when it is substituted with two or more halogens, then the halogens may be same or different;
- and the phenyl group may optionally have one or more substituents selected from Group 5, provided that when it has two or more substituents, then the substituents may be same or different;
- the Group 5 consists of halogen, a C1-C6 alkyl group, and a C1-C6 alkoxy group;
- in the Group 5, the C1-C6 alkyl group and the C1-C6 alkoxy group may be optionally substituted with one or more halogens, provided that when they are substituted with two or more halogens, then the halogens may be same or different;
- G represents a C6-C10 aryl group, a 5- or 6-membered heteroaryl group, or an 8- to 10-membered fused heteroaryl group;
- wherein the C6-C10 aryl group, the 5- or 6-membered heteroaryl group, and the 8- to 10-membered fused heteroaryl group may optionally have one or more substituents selected from Group R4, provided that when they have two or more substituents, then the substituents may be same or different;
- the Group R4 consists of halogen, a cyano group, a nitro group, a formyl group, a C1-C6 alkyl group, a C1-C6 alkoxy group, a (C1-C6 alkoxy)C1-C6 alkyl group, a C2-C6 alkenyl group, a C2-C6 alkynyl group, a C3-C6 cycloalkyl group, a C1-C6 alkylthio group, a C1-C6 alkylsulfinyl group, a C1-C6 alkylsulfonyl group, as C1-C6 alkylamino group, a di(C1-C6 alkyl)amino group, a C3-C6 cycloalkylamino group, a (C1-C6 alkyl)carbonyl group, a (C3-C6 cycloalkyl)carbonyl group, a (C1-C6 alkoxy)carbonyl group, a (C1-C6 alkylamino)carbonyl group, a di(C1-C6 alkyl)aminocarbonyl group, a (C3-C6 cycloalkylamino)carbonyl group, a tri(C1-C6 alkyl)silyl group, a C6-C10 aryl group, and a 5- or 6-membered heteroaryl group;
- in the Group R4, the C1-C6 alkyl group, the C1-C6 alkoxy group, the (C1-C6 alkoxy)C1-C6 alkyl group, the C2-C6 alkenyl group, the C2-C6 alkynyl group, the C3-C6 cycloalkyl group, the C1-C6 alkylthio group, the C1-C6 alkylsulfinyl group, the C1-C6 alkylsulfonyl group, the (C1-C6 group, the (C3-C6 cycloalkyl)carbonyl group, and the (C1-C6 alkoxy)carbonyl group may be optionally substituted with one or more halogens, provided that when they are substituted with two or more halogens, then the halogens may be same or different;
- and the C6-C10 aryl group and the 5- or 6-membered heteroaryl group may optionally have one or more substituents selected from Group 4, provided that when they have two or more substituents, then the substituents may be same or different;
- the Group 4 consists of halogen, a cyano group, a nitro group, a formyl group, a C1-C6 alkyl group, a C1-C5 alkoxy group, a (C1-C6 alkoxy)C1-C6 alkyl group, a C2-C6 alkenyl group, a C2-C6 alkynyl group, a C3-C6 cycloalkyl group, a C1-C6 alkylthio group, a C1-C6 alkylsulfinyl group, a C1-C6 alkylsulfonyl group, a C1-C6 alkylamino group, a di(C1-C6 alkyl)amino group, a C3-C6 cycloalkylamino group, a (C1-C6 alkyl)carbonyl group, a (C3-C6 cycloalkyl)carbonyl group, a (C1-C6 alkoxy)carbonyl group, a (C1-C6 alkylamino)carbonyl group, a di(C1-C6 alkyl)aminocarbonyl group, a (C3-C6 cycloalkylamino)carbonyl group, and a tri(C1-C6 alkyl)silyl group;
- in the Group 4, the C1-C6 alkyl group, the C1-C6 alkoxy group, the (C1-C6 alkoxy)C1-C6 alkyl group, the C2-C6 alkenyl group, the C2-C6 alkynyl group, the C3-C6 cycloalkyl group, the C1-C6 alkylthio group, the C1-C6 alkylsulfinyl group, the C1-C6 alkylsulfonyl group, the (C1-C6 alkyl)carbonyl group, the (C3-C6 cycloalkyl)carbonyl group, and the (C1-C6 alkoxy)carbonyl group may be optionally substituted with one or more halogens, provided that when they are substituted with two or more halogens, then the halogens may be same or different;
- n represents an integer of 0, 1 or 2;
- V represents an integer of 1 or 2;
- and
- M represents an alkali metal when V is an integer of 1, and M represents an alkali earth metal when V is an integer of 2.
A method for producing a compound of the formula (4):
- which comprises reacting a compound of the formula (7):
- with a compound of the formula (12):
- wherein the symbols in the formulae (4), (7) and (12) are defined as follows:
- R2 represents hydrogen, a C1-C6 alkyl group, a (C1-C6 alkoxy)C1-C6 alkyl group, a C2-C6 alkenyl group, a C2-C6 alkynyl group, a C3-C6 cycloalkyl group, a (C1-C6 alkylthio)C1-C6 alkyl group, a (C1-C6 alkylsulfinyl)C1-C6 alkyl group, a (C1-C6 alkylsulfonyl)C1-C6 alkyl group, a phenyl group, or a 5- or 6-membered heteroaryl group;
- wherein the C1-C6 alkyl group, the (C1-C6 alkoxy)C1-C6 alkyl group, the C2-C6 alkenyl group, the C2-C6 alkynyl group, the C3-C6 cycloalkyl group, the (C1-C6 alkylthio)C1-C6 alkyl group, the (C1-C6 alkylsulfinyl)C1-C6 alkyl group, and the (C1-C6 alkylsulfonyl)C1-C6 alkyl group may be optionally substituted with one or more halogens, provided that when they are substituted with two or more halogens, then the halogens may be same or different;
- and the phenyl group and the 5- or 6-membered heteroaryl group may optionally have one or more substituents selected from Group 2, provided that when they have two or more substituents, then the substituents may be same or different;
- the Group 2 consists of halogen, a cyano group, a nitro group, a formyl group, a C1-C6 alkyl group, a C1-C6 alkoxy group, a (C1-C6 alkoxy)C1-C6 alkyl group, a C2-C6 alkenyl group, a C2-C6 alkynyl group, a C3-C6 cycloalkyl group, a C1-C6 alkylthio group, a C1-C6 alkylsulfinyl group, a C1-C6 alkylsulfonyl group, as C1-C6 alkylamino group, a di(C1-C6 alkyl)amino group, a C3-C6 cycloalkylamino group, a (C1-C6 alkyl)carbonyl group, a (C3-C6 cycloalkyl)carbonyl group, a (C1-C6 alkoxy)carbonyl group, a (C1-C6 alkylamino)carbonyl group, a di(C1-C6 alkyl)aminocarbonyl group, a (C3-C6 cycloalkylaminocarbonyl group, and a tri(C1-C6 alkyl)silyl group;
- in the Group 2, the C1-C6 alkyl group, the C1-C6 alkoxy group, the (C1-C6 alkoxy)C1-C6 alkyl group, the C2-C6 alkenyl group, the C2-C6 alkynyl group, the C3-C6 cycloalkyl group, the C1-C6 alkylthio group, the C1-C6 alkylsulfinyl group, the C1-C6 alkylsulfonyl group, the (C1-C6 alkyl)carbonyl group, the (C3-C6 cycloalkyl)carbonyl group, and the (C1-C6 alkoxy)carbonyl group may be optionally substituted with one or more halogens, provided that when they are substituted with two or more halogens, then the halogens may be same or different;
- R3 represents hydrogen, a C1-C6 alkyl group, a (C1-C6 alkoxy)C1-C6 alkyl group, a C2-C6 alkenyl group, a C2-C6 alkynyl group, a C3-C6 cycloalkyl group, a (C1-C6 alkylthio)C1-C6 alkyl group, a C1-C6 alkylsulfonyl group, a (C1-C6 alkyl)carbonyl group, a (C1-C6 alkoxy)carbonyl group, a (C1-C6 alkylamino)carbonyl group, a di(C1-C6 alkyl)aminocarbonyl group, a (C3-C6 cycloalkylamino)carbonyl group, a phenyl group, a benzyl group, or a phenylsulfonyl group;
- wherein the C1-C6 alkyl group, the (C1-C6 alkoxy)C1-C6 alkyl group, the C2-C6 alkenyl group, the C2-C6 alkynyl group, the C3-C6 cycloalkyl group, the (C1-C6 alkylthio)C1-C6 alkyl group, the C1-C6 alkylsulfonyl group, the (C1-C6 alkyl)carbonyl group, and the (C1-C6 alkoxy)carbonyl group may be optionally substituted with one or more halogens, provided that when they are substituted with two or more halogens, then the halogens may be same or different;
- and the phenyl group, the benzyl group, and the phenylsulfonyl group may optionally have one or more substituents selected from Group 3, provided that when they have two or more substituents, then the substituents may be same or different;
- the Group 3 consists of halogen, a C1-C6 alkyl group, a C1-C6 alkoxy group, and a (C1-C6 alkoxy)C1-C6 alkyl group;
- in the Group 3, the C1-C6 alkyl group, the C1-C6 alkoxy group, and the (C1-C6 alkoxy)C1-C6 alkyl group may be optionally substituted with one or more halogens, provided that when they are substituted with two or more halogens, then the halogens may be same or different;
- R5 represents a C1-C6 alkyl group or a phenyl group;
- wherein the C1-C6 alkyl group may be optionally substituted with one or more halogens, provided that when it is substituted with two or more halogens, then the halogens may be same or different;
- and the phenyl group may optionally have one or more substituents selected from Group 5, provided that when it has two or more substituents, then the substituents may be same or different;
- the Group 5 consists of halogen, a C1-C6 alkyl group, and a C1-C6 alkoxy group;
- in the Group 5, the C1-C6 alkyl group and the C1-C6 alkoxy group may be optionally substituted with one or more halogens, provided that when they are substituted with two or more halogens, then the halogens may be same or different;
- G represents a C6-C10 aryl group, a 5- or 6-membered heteroaryl group, or an 8- to 10-membered fused heteroaryl group;
- wherein the C6-C10 aryl group, the 5- or 6-membered heteroaryl group, and the 8- to 10-membered fused heteroaryl group may optionally have one or more substituents selected from Group R4, provided that when they have two or more substituents, then the substituents may be same or different;
- the Group R4 consists of halogen, a cyano group, a nitro group, a formyl group, a C1-C6 alkyl group, a C1-C6 alkoxy group, a (C1-C6 alkoxy)C1-C6 alkyl group, a C2-C6 alkenyl group, a C2-C6 alkynyl group, a C3-C6 cycloalkyl group, a C1-C6 alkylthio group, a C1-C6 alkylsulfinyl group, a C1-C6 all group, a C1-C6 alkylamino group, a di(C1-C6 alkyl)amino group, a C3-C6 cycloalkylamino group, a (C1-C6 alkyl)carbonyl group, a (C3-C6 cycloalkyl)carbonyl group, a (C1-C6 alkoxy)carbonyl group, a (C1-C6 alkylamino)carbonyl group, a di(C1-C6 alkyl)aminocarbonyl group, a (C3-C6 cycloalkylamino)carbonyl group, a tri(C1-C6 alkyl)silyl group, a C6-C10 aryl group, and a 5- or 6-membered heteroaryl group;
- in the Group R4, the C1-C6 alkyl group, the C1-C6 alkoxy group, the (C1-C6 alkoxy)C1-C6 alkyl group, the C2-C6 alkenyl group, the C2-C6 alkynyl group, the C3-C6 cycloalkyl group, the C1-C6 alkylthio group, the C1-C6 alkylsulfinyl group, the C1-C6 alkylsulfonyl group, the (C1-C6 alkyl)carbonyl group, the (C3-C6 cycloalkyl)carbonyl group, and the (C1-C6 alkoxy)carbonyl group may be optionally substituted with one or more halogens, provided that when they are substituted with two or more halogens, then the halogens may be same or different;
- and the C6-C10 aryl group and the 5- or 6-membered heteroaryl group may optionally have one or more substituents selected from Group 4, provided that when they have two or more substituents, then the substituents may be same or different;
- the Group 4 consists of halogen, a cyano group, a nitro group, a formyl group, a C1-C6 alkyl group, a C1-C6 alkoxy group, a (C1-C6 alkoxy)C1-C6 alkyl group, a C2-C6 alkenyl group, a C2-C6 alkynyl group, a C3-C6 cycloalkyl group, a C1-C6 alkylthio group, a C1-C6 alkylsulfinyl group, a C1-C6 alkylsulfonyl group, a C1-C6 alkylamino group, a di(C1-C6 alkyl)amino group, a C3-C6 cycloalkylamino group, a (C1-C6 alkyl)carbonyl group, a (C3-C6 cycloalkyl)carbonyl group, a (C1-C6 alkoxy)carbonyl group, a (C1-C6 alkylamino)carbonyl group, a di(C1-C6 alkyl)aminocarbonyl group, a (C3-C6 cycloalkylamino)carbonyl group, and a tri(C1-C6 alkyl)silyl group;
- in the Group 4, the C1-C6 alkyl group, the C1-C6 alkoxy group, the (C1-C6 alkoxy)C1-C6 alkyl group, the C2-C6 alkenyl group, the C2-C6 alkynyl group, the C3-C6 cycloalkyl group, the C1-C6 alkylthio group, the C1-C6 alkylsulfinyl group, the C1-C6 alkylsulfonyl group, the (C1-C6 alkyl)carbonyl group, the (C3-C6 cycloalkyl)carbonyl group, and the (C1-C6 alkoxy)carbonyl group may be optionally substituted with one or more halogens, provided that when they are substituted with two or more halogens, then the halogens may be same or different;
- and
- n represents an integer of 0, 1 or 2.
A method for producing a compound of the formula (2*-O2):
- which comprises reacting a compound of the formula (2*-O4
- or a compound of the formula (2*-O1):
- with an oxidizing agent;
- wherein the symbols in the formulae (2*-O2), (2*-O0) and (2*-O1) are defined as follows:
- R2* represents hydrogen, a C1-C6 alkyl group, a phenyl group, or a 5- or 6-membered heteroaryl group;
- wherein the C1-C6 alkyl group may be optionally substituted with one or more halogens, provided that when it is substituted with two or more halogens, then the halogens may be same or different;
- and the phenyl group and the 5- or 6-membered heteroaryl group may optionally have one or more substituents selected from Group 2*, provided that when they have two or more substituents, then the substituents may be same or different;
- the Group 2* consists of halogen and a C1-C6 alkyl group;
- in the Group 2*, the C1-C6 alkyl group may be optionally substituted with one or more halogens, provided that when it is substituted with two or more halogens, then the halogens may be same or different:
- R3* represents hydrogen, a C1-C6 alkyl group, or a (C1-C6 alkoxy)C1-C6 alkyl group;
- wherein the C1-C6 alkyl group and the (C1-C6 alkoxy)C1-C6 alkyl group may be optionally substituted with one or more halogens, provided that when they are substituted with two or more halogens, then the halogens may be same or different;
- R5* represents a C1-C6 alkyl group or a phenyl group;
- wherein the C1-C6 alkyl group may be optionally substituted with one or more halogens, provided that when it is substituted with two or more halogens, then the halogens may be same or different;
- and the phenyl group may optionally have one or more substituents selected from Group 5*, provided that when it has two or more substituents, then the substituents may be same or different;
- the Group 5* consists of halogen, a C1-C6 alkyl group, and a C1-C6 alkoxy group.
- in the Group 5*, the C1-C6 alkyl group and the C1-C6 alkoxy group may be optionally substituted with one or more halogens, provided that when they are substituted with two or more halogens, then the halogens may be same or different;
- and
- G* is a phenyl group;
- wherein the phenyl group may optionally have one or more substituents selected from Group R4*, provided that when it has two or more substituents, then the substituents may be same or different;
- the Group R4* consists of halogen, a cyano group, a nitro group, a formyl group, a C1-C6 alkyl group, a C1-C6 alkoxy group, a (C1-C6 alkoxy)C1-C6 alkyl group, a C2-C6 alkenyl group, a C2-C6 alkynyl group, a C3-C6 cycloalkyl group, a C1-C6 alkylthio group, a C1-C6 alkylsulfinyl group, a C1-C6 alkylsulfonyl group, a C1-C6 alkylamino group, a di(C1-C6 alkyl)amino group, a C3-C6 cycloalkylamino group, a (C1-C6 alkyl)carbonyl group, a (C3-C6 cycloalkyl)carbonyl group, a (C1-C6 alkoxy)carbonyl group, a (C1-C6 alkylamino)carbonyl group, a di(C1-C6 alkyl)aminocarbonyl group, a (C3-C6 cycloalkylamino)carbonyl group, a tri(C1-C6 alkyl)silyl group, a C6-C10 aryl group, and a 5- or 6-membered heteroaryl group;
- in the Group R4*, the C1-C6 alkyl group, the C1-C6 alkoxy group, the (C1-C6 alkoxy)C1-C6 alkyl group, the C2-C6 alkenyl group, the C2-C6 alkynyl group, the C3-C6 cycloalkyl group, the C1-C6 alkylthio group, the C1-C6 alkylsulfinyl group, the C1-C6 alkylsulfonyl group, the (C1-C6 alkyl)carbonyl group, the (C3-C6 cycloalkyl)carbonyl group, and the (C1-C6 alkoxy)carbonyl group may be optionally substituted with one or more halogens, provided that when they are substituted with two or more halogens, then the halogens may be same or different;
- and the C6-C10 aryl group and the 5- or 6-membered heteroaryl group may optionally have one or more substituents selected from Group 4*, provided that when they have two or more substituents, then the substituents may be same or different;
- the Group 4* consists of halogen, as cyano group, a nitro group, a formyl group, a C1-C6 alkyl group, a C1-C5 alkoxy group, a (C1-C6 alkoxy)C1-C6 alkyl group, a C2-C6 alkenyl group, a C2-C6 alkynyl group, a C3-C6 cycloalkyl group, a C1-C6 alkylthio group, a C1-C6 alkylsulfinyl group, a C1-C6 alkylsulfonyl group, a C1-C6 alkylamino group, a di(C1-C6 alkyl)amino group, a C3-C6 cycloalkylamino group, a (C1-C6 alkyl)carbonyl group, a (C3-C6 cycloalkyl)carbonyl group, a (C1-C6 alkoxy)carbonyl group, a (C1-C6 alkylamino)carbonyl group, a di(C1-C6 alkyl)aminocarbonyl group, a (C3-C6 cycloalkylamino)carbonyl group, and a tri(C1-C6 alkyl)silyl group;
- in the Group 4*, the C1-C6 alkyl group, the C1-C6 alkoxy group, the (C1-C6 alkoxy)C1-C6 alkyl group, the C2-C6 alkenyl group, the C2-C6 alkynyl group, the C3-C6 cycloalkyl group, the C1-C6 alkylthio group, the C1-C6 alkylsulfinyl group, the C1-C6 alkylsulfonyl group, the (C1-C6 alkyl)carbonyl group, the (C3-C6 cycloalkyl)carbonyl group, and the (C1-C6 alkoxy)carbonyl group may be optionally substituted with one or more halogens, provided that when they are substituted with two or more halogens, then the halogens may be same or different.
A method for producing a compound of the formula (2*-O1):
- which comprises reacting a compound of the formula (2*-O0):
- with an oxidizing agent;
- wherein the symbols in the formulae (2*-O0) and (2*-O1) are defined as follows:
- R2* represents hydrogen, a C1-C6 alkyl group, a phenyl group, or a 5- or 6-membered heteroaryl group;
- wherein the C1-C6 alkyl group may be optionally substituted with one or more halogens, provided that when it is substituted with two or more halogens, then the halogens may be same or different;
- and the phenyl group and the 5- or 6-membered heteroaryl group may optionally have one or more substituents selected from Group 2*, provided that when they have two or more substituents, then the substituents may be same or different;
- the Group 2* consists of halogen and a C1-C6 alkyl group;
- in the Group 2*, the C1-C6 alkyl group may be optionally substituted with one or more halogens, provided that when it is substituted with two or more halogens, then the halogens may be same or different;
- R3* is hydrogen, a C1-C6 alkyl group, or a (C1-C6 alkoxy)C1-C6 alkyl group;
- wherein the C1-C6 alkyl group and the (C1-C6 alkoxy)C1-C6 alkyl group may be optionally substituted with one or more halogens, provided that when they are substituted with two or more halogens, then the halogens may be same or different;
- R5* represents a C1-C6 alkyl group or a phenyl group;
- wherein the C1-C6 alkyl group may be optionally substituted with one or more halogens, provided that when it is substituted with two or more halogens, then the halogens may be same or different;
- and the phenyl group may optionally have one or more substituents selected from Group 5*, provided that when it has two or more substituents, then the substituents may be same or different;
- the Group 5* consists of halogen, a C1-C6 alkyl group, and a C1-C6 alkoxy group;
- in the Group 5*, the C1-C6 alkyl group and the C1-C6 alkoxy group may be optionally substituted with one or more halogens, provided that when they are substituted with two or more halogens;
- then the halogens may be same or different;
- and
- G* represents a phenyl group;
- wherein the phenyl group may optionally have one or more substituents selected from Group R4*, provided that when it has two or more substituents, then the substituents may be same or different;
- the Group R4* consists of halogen, a cyano group, a nitro group, a formyl group, a C1-C6 alkyl group, a C1-C6 alkoxy group, a (C1-C6 alkoxy)C1-C6 alkyl group, a C2-C6 alkenyl group, a C2-C6 alkynyl group, a C3-C6 cycloalkyl group, a C1-C6 alkylthio group, a C1-C6 alkylsulfinyl group, a C1-C6 alkylsulfonyl group, a C1-C6 alkylamino group, a di(C1-C6 alkyl)amino group, a C3-C6 cycloalkylamino group, a (C1-C6 alkyl)carbonyl group, a (C3-C6 cycloalkyl)carbonyl group, a (C1-C6 alkoxy)carbonyl group, a (C1-C6 alkylamino)carbonyl group, a di(C1-C6 alkyl)aminocarbonyl group, a (C3-C6 cycloalkylamino)carbonyl group, a tri(C1-C6 alkyl)silyl group, a C6-C10 aryl group, and a 5- or 6-membered heteroaryl group;
- in the Group R4*, the C1-C6 alkyl group, the C1-C6 alkoxy group, the (C1-C6 alkoxy)C1-C6 alkyl group, the C2-C6 alkenyl group, the C2-C6 alkynyl group, the C3-C6 cycloalkyl group, the C1-C6 alkylthio group, the C1-C6 alkylsulfinyl group, the C1-C6 alkylsulfonyl group, the (C1-C6 alkyl)carbonyl group, the (C3-C6 cycloalkyl)carbonyl group, and the (C1-C6 alkoxy)carbonyl group may be optionally substituted with one or more halogens, provided that when it is substituted with two or more halogens, then the halogens may be same or different;
- and the C6-C10 aryl group and the 5- or 6-membered heteroaryl group may optionally have one or more substituents selected from Group 4*, provided that when they have two or more substituents, then the substituents may be same or different;
- the Group 4* consists of halogen, a cyano group, a nitro group, a formyl group, a C1-C6 alkyl group, a C1-C6 alkoxy group, a (C1-C6 alkoxy)C1-C6 alkyl group, a C2-C6 alkenyl group, a C2-C6 alkynyl group, a C3-C6 cycloalkyl group, a C1-C6 alkylthio group, a C1-C6 alkylsulfinyl group, a C1-C6 alkylsulfonyl group, a C1-C6 alkylamino group, a di(C1-C6 alkyl)amino group, a C3-C6 cycloalkylamino group, a (C1-C6 alkyl)carbonyl group, a (C3-C6 cycloalkyl)carbonyl group, a (C1-C6 alkoxy)carbonyl group, a (C1-C6 alkylamino)carbonyl group, a di(C1-C6 alkyl)aminocarbonyl group, a (C3-C6 cycloalkylamino)carbonyl group, and a tri(C1-C6 alkyl)silyl group;
- in the Group 4*, the C1-C6 alkyl group, the C1-C6 alkoxy group, the (C1-C6 alkoxy)C1-C6 alkyl group, the C2-C6 alkenyl group, the C2-C6 alkynyl group, the C3-C6 cycloalkyl group, the C1-C6 alkylthio group, the C1-C6 alkylsulfinyl group, the C1-C6 alkylsulfonyl group, the (C1-C6 alkyl)carbonyl group, the (C3-C6 cycloalkyl)carbonyl group, and the (C1-C6 alkoxy)carbonyl group may be optionally substituted with one or more halogens, provided, that when they are substituted with two or more halogens, then the halogens may be same or different.
A compound of the formula (2A):
- wherein the symbols in the formula (2A) are defined as follows:
- R2-2A represents hydrogen, a C1-C6 alkyl group, or a phenyl group;
- wherein the C1-C6 alkyl group may be optionally substituted with one or more halogens, provided that when it is substituted with two or more halogens, then the halogens may be same or different;
- and the phenyl group may optionally have one or more substituents selected from Group 2-2A, provided that when it has two or more substituents, then the substituents may be same or different:
- the Group 2-2A consists of halogen and a C1-C6 alkyl group;
- in the Group 2-2A, the C1-C6 alkyl group may be optionally substituted with one or more halogens, provided that when it is substituted with two or more halogens, then the halogens may be same or different
- R3-2A represents hydrogen, a C1-C6 alkyl group, a (C1-C6 alkoxy)C1-C6 alkyl group, or a benzyl group;
- wherein the C1-C6 alkyl group and the (C1-C6 alkoxy)C1-C6 alkyl group may be optionally substituted with one or more halogens, provided that when they are substituted with two or more halogens, then the halogens may be same or different:
- and the benzyl group may optionally have one or more substituents selected from the group consisting of halogen, C1-C6 alkyl group, and C1-C6 alkoxy group, provided that when it has two or more substituents, then the substituents may be same or different;
- R5-2A represents a C1-C6 alkyl group or a phenyl group;
- wherein the C1-C6 alkyl group may be optionally substituted with one or more halogens, provided that when it is substituted with two or more halogens, then the halogens may be same or different, and
- the phenyl group may optionally have one or more substituents selected from Group 5-2A, provided that when it has two or more substituents, then the substituents may be same or different;
- the Group 5-2A consists of halogen, a C1-C6 alkyl group, and a C1-C6 alkoxy group;
- in the Group 5-2A, the C1-C6 alkyl group and the C1-C6 alkoxy group may be optionally substituted with one or more halogens, provided that when they are substituted with two or more halogens, then the halogens may be same or different;
- G2A represents a phenyl group having one or more substituents selected from Group R4-2A or a 5- or 6-membered heteroaryl group having one or more substituents selected from the Group R4-2A;
- wherein the substituents may be same or different when the phenyl group and 5- or 6-membered heteroaryl group have two or more substituents;
- and the phenyl group has two or more substituents when n is an integer of 0;
- the Group R4-2A consists of halogen, a cyano group, a nitro group, a formyl group, a C1-C6 alkyl group, a C1-C6 alkoxy group, a (C1-C6 alkoxy)C1-C6 alkyl group, a C2-C6 alkenyl group, a C2-C6 alkynyl group, a C3-C6 cycloalkyl group, a C1-C6 alkylthio group, a C1-C6 alkylsulfinyl group, a (C1-C6 alkyl)carbonyl group, a (C3-C6 cycloalkyl)carbonyl group, a (C1-C6 alkoxy)carbonyl group, a (C1-C6 alkylamino)carbonyl group, a di(C1-C6 alkyl)aminocarbonyl group, a (C3-C6 cycloalkylamino)carbonyl group, a tri(C1-C6 alkyl)silyl group, a C6-C10 aryl group, and a 5- or 6-membered heteroaryl group;
- in the Group R4-2A, the C1-C6 alkyl group, the C1-C6 alkoxy group, the (C1-C6 alkoxy)C1-C6 alkyl group, the C2-C6 alkenyl group, the C2-C6 alkynyl group, the C3-C6 cycloalkyl group, the C1-C6 alkylthio group, the C1-C6 alkylsulfinyl group, the (C1-C6 alkyl)carbonyl group, the (C3-C6 cycloalkyl)carbonyl group, and the (C1-C6 alkoxy)carbonyl group may be optionally substituted with one or more halogens, provided that when they are substituted with two or more halogens, then the halogens may be same or different;
- and the C6-C10 aryl group and the 5- or 6-membered heteroaryl group may optionally have one or more substituents selected from Group 4-2A, provided that when they have two or more substituents, then the substituents may be same or different;
- the Group 4-2A consists of halogen, a cyano group, a intro group, a formyl group, a C1-C6 alkyl group, a C1-C6 alkoxy group, a (C1-C6 alkoxy)C1-C6 alkyl group, a C2-C6 alkenyl group, a C2-C6 alkynyl group, a C3-C6 cycloalkyl group, a C1-C6 alkylthio group, a C1-C6 alkylsulfinyl group, a C1-C6 alkylsulfonyl group, a C1-C6 alkylamino group, a di(C1-C6 alkyl)amino group, a C3-C6 cycloalkylamino group, a (C1-C6 alkyl)carbonyl group, a (C3-C6 cycloalkyl)carbonyl group, a (C1-C6 alkoxy)carbonyl group, a (C1-C6 alkylamino)carbonyl group, a di(C1-C6 alkyl)aminocarbonyl group, a (C3-C6 cycloalkylamino)carbonyl group, and a tri(C1-C6 alkyl)silyl group;
- in the Group 4-2A, the C1-C6 alkyl group, the C1-C6 alkoxy group, the (C1-C6 alkoxy)C1-C6 alkyl group, the C2-C6 alkenyl group, the C2-C6 alkynyl group, the C3-C6 cycloalkyl group, the C1-C6 alkylthio group, the C1-C6 alkylsulfinyl group, the C1-C6 alkylsulfonyl group, the (C1-C6 alkyl)carbonyl group, the (C3-C6 cycloalkyl)carbonyl group, and the (C1-C6 alkoxy)carbonyl group may be optionally substituted with one or more halogens, provided that when they are substituted with two or more halogens, then the halogens may be same or different;
- and
- n represents an integer of 0, 1 or 2.
A compound of the formula (4A):
- wherein the symbols in the formula (4A) are defined as follows:
- R2-4A represents hydrogen, a C1-C6 alkyl group, a (C1-C6 alkoxy)C1-C6 alkyl group, a C2-C6 alkenyl group, a C2-C6 alkynyl group, a C3-C6 cycloalkyl group, a (C1-C6 alkylthio)C1-C6 alkyl group, a (C1-C6 alkylsulfinyl)C1-C6 alkyl group, a (C1-C6 alkylsulfonyl)C1-C6 alkyl group, a phenyl group, or a 5- or 6-membered heteroaryl group;
- wherein the C1-C6 alkyl group, the (C1-C6 alkoxy)C1-C6 alkyl group, the C2-C6 alkenyl group, the C2-C6 alkynyl group, the C3-C6 cycloalkyl group, the (C1-C6 alkylthio)C1-C6 alkyl group, the (C1-C6 alkylsulfinyl)C1-C6 alkyl group, and the (C1-C6 alkylsulfonyl)C1-C6 alkyl group may be optionally substituted with one or more halogens, provided that when they are substituted with two or more halogens, then the halogens may be same or different, the phenyl group and the 5- or 6-membered heteroaryl group may optionally have one or more substituents selected from Group 2-4A, provided that when they have two or more substituents, then the substituents may be same or different;
- the Group 2-4A consists of halogen, a cyano group, a nitro group, a formyl group, a C1-C6 alkyl group, a C1-C6 alkoxy group, a (C1-C6 alkoxy)C1-C6 alkyl group, a C2-C6 alkenyl group, a C2-C6 alkynyl group, a C3-C6 cycloalkyl group, a C1-C6 alkylthio group, a C1-C6 alkylsulfinyl group, a C1-C6 alkylsulfonyl group, a C1-C6 alkylamino group, a di(C1-C6 alkyl)amino group, a C3-C6 cycloalkylamino group, a (C1-C6 alkyl)carbonyl group, a (C3-C6 cycloalkyl)carbonyl group, a (C1-C6 alkoxy)carbonyl group, a (C1-C6 alkylamino)carbonyl group, a di(C1-C6 alkyl)aminocarbonyl group, a (C3-C6 cycloalkylamino)carbonyl group, and a tri(C1-C6 alkyl)silyl group;
- in the Group 2-4A, the C1-C6 alkyl group, the C1-C6 alkoxy group, the (C1-C6 alkoxy)C1-C6 alkyl group, the C2-C6 alkenyl group, the C2-C6 alkynyl group, the C3-C6 cycloalkyl group, the C1-C6 alkylthio group, the C1-C6 alkylsulfinyl group, the C1-C6 alkylsulfonyl group, the (C1-C6 alkyl)carbonyl group, the (C3-C6 cycloalkyl)carbonyl group, and the (C1-C6 alkoxy)carbonyl group may be optionally substituted with one or more halogens, provided that when they are substituted with two or more halogens, then the halogens may be same or different;
- R3-4A represents hydrogen, a C1-C6 alkyl group, a (C1-C6 alkoxy)C1-C6 alkyl group, a C2-C6 alkenyl group, a C2-C6 alkynyl group, a C3-C6 cycloalkyl group, a (C1-C6 alkylthio)C1-C6 alkyl group, a C1-C6 alkylsulfonyl group, a (C1-C6 alkyl)carbonyl group, a (C1-C6 alkoxy)carbonyl group, a (C1-C6 alkylamino)carbonyl group, a di(C1-C6 alkyl)aminocarbonyl group, a (C3-C6 cycloalkylamino)carbonyl group, a phenyl group, a benzyl group, or a phenylsulfonyl group;
- wherein the C1-C6 alkyl group, the (C1-C6 alkoxy)C1-C6 alkyl group, the C2-C6 alkenyl group, the C2-C6 alkynyl group, the C3-C6 cycloalkyl group, the (C1-C6 alkylthio)C1-C6 alkyl group, the C1-C6 alkylsulfonyl group, the (C1-C6 alkyl)carbonyl group, and the (C1-C6 alkoxy)carbonyl group may be optionally substituted with one or more halogens, provided that when they are substituted with two or more halogens, then the halogens may be same or different and the phenyl group, the benzyl group, and the phenylsulfonyl group may optionally have one or more substituents selected from Group 3-4A, provided that When they have two or more substituents, then the substituents may be same or different;
- the Group 3-4A consists of halogen, as C1-C6 alkyl group, a C1-C6 alkoxy group, and a (C1-C6 alkoxy)C1-C6 alkyl group;
- in the Group 3-4A, the C1-C6 alkyl group, the C1-C6 alkoxy group, and the (C1-C6 alkoxy)C1-C6 alkyl group may be optionally substituted with one or more halogens, provided that when they are substituted with two or more halogens, then the halogens may be same or different;
- R5-4A represents a C1-C6 alkyl group or a phenyl group;
- wherein the C1-C6 alkyl group may be optionally substituted with one or more halogens, provided that when it is substituted with two or more halogens, then the halogens may be same or different;
- and the phenyl group may optionally have one or more substituents selected from Group 5-4A, provided that when it has two or more substituents, then the substituents may be same or different;
- the Group 5-4A consists of halogen, a C1-C6 alkyl group, and a C1-C6 alkoxy group;
- in the Group 5-4A, the C1-C6 alkyl group, and the C1-C6 alkoxy group may be optionally substituted with one or more halogens, provided that when they are substituted with two or more halogens, then the halogens may be same or different;
- G4A represents a C6-C10 aryl group, a 5- or 6-membered heteroaryl group, or an 8- to 10-membered fused heteroaryl group;
- wherein the C6-C10 aryl group, the 5- or 6-membered heteroaryl group, and the 8- to 10-membered fused heteroaryl group may optionally have one or more substituents selected from Group R4-4A, provided that when they have two or more substituents, then the substituents may be same or different;
- the Group R4-4A consists of halogen, a cyano group, a nitro group, a formyl group, a C1-C6 alkyl group, a C1-C6 alkoxy group, a (C1-C6 alkoxy)C1-C6 alkyl group, a C2-C6 alkenyl group, a C2-C6 alkynyl group, a C3-C6 cycloalkyl group, a C1-C6 alkylthio group, a C1-C6 alkylsulfinyl group, a C1-C6 alkylsulfonyl group, a C1-C6 alkylamino group, a di(C1-C6 alkyl)amino group, a C3-C6 cycloalkylamino group, a (C1-C6 alkyl)carbonyl group, a (C3-C6 cycloalkyl)carbonyl group, a (C1-C6 alkoxy)carbonyl group, a (C1-C6 alkylamino)carbonyl group, a di(C1-C6 alkyl aminocarbonyl group, as (C3-C6 cycloalkylamino)carbonyl group, a tri(C1-C6 alkyl)silyl group, a C6-C10 aryl group, and a 5- or 6-membered heteroaryl group;
- in the Group R4-4A, the C1-C6 alkyl group, the C1-C6 alkoxy group, the (C1-C6 alkoxy)C1-C6 alkyl group, the C2-C6 alkenyl group, the C2-C6 alkynyl group, the C3-C6 cycloalkyl group, the C1-C6 alkylthio group, the C1-C6 alkylsulfinyl group, the C1-C6 alkylsulfonyl group, the (C1-C6 alkyl)carbonyl group, the (C3-C6 cycloalkyl)carbonyl group, and the (C1-C6 alkoxy)carbonyl group may be optionally substituted with one or more halogens, provided that When they are substituted with two or more halogens, then the halogens may be same or different;
- and the C6-C10 aryl group and the 5- or 6-membered heteroaryl group may optionally have one or more substituents selected from Group 4-4A, provided that when they have two or more substituents, then the substituents may be same or different;
- the Group 4-4A consists of halogen, a cyano group, a nitro group, a formyl group, a C1-C6 alkyl group, a C1-C6 alkoxy group, a (C1-C6 alkoxy)C1-C6 alkyl group, a C2-C6 alkenyl group, a C2-C6 alkynyl group, a C3-C6 cycloalkyl group, a C1-C6 alkylthio group, a C1-C6 alkylsulfinyl group, a C1-C6 alkylsulfonyl group, as C1-C6 alkylamino group, a di(C1-C6 alkyl)amino group, a C3-C6 cycloalkylamino group, a (C1-C6 alkyl)carbonyl group, a (C3-C6 cycloalkyl)carbonyl group, a (C1-C6 alkoxy)carbonyl group, a (C1-C6 alkylamino)carbonyl group, a di(C1-C6 alkyl)aminocarbonyl group, a (C3-C6 cycloalkylaminocarbonyl group, and a tri(C1-C6 alkyl)silyl group;
- in the Group 4-4A, the C1-C6 alkyl group, the C1-C6 alkoxy group, the (C alkoxy)C1-C6 alkyl group, the C2-C6 alkenyl group, the C2-C6 alkynyl group, the C3-C6 cycloalkyl group, the C1-C6 alkylthio group, the C1-C6 alkylsulfinyl group, the C1-C6 alkylsulfonyl group, the (C1-C6 alkyl)carbonyl group, the (C3-C6 cycloalkyl)carbonyl group, and the (C1-C6 alkoxy)carbonyl group may be optionally substituted with one or more halogens, provided that when they are substituted with two or more halogens, then the halogens may be same or different;
- and
- n represents an integer of 0, 1 or 2.
A compound of the formula (5A):
- wherein the symbols in the formula (5A) are defined as follows:
- R2-5A represents hydrogen, a C1-C6 alkyl group, a phenyl group, or a 5- or 6-membered heteroaryl group;
- wherein the C1-C6 alkyl group may be optionally substituted with one or more halogens, provided that when it is substituted with two or more halogens, then the halogens may be same or different;
- and the phenyl group and the 5- or 6-membered heteroaryl group may optionally have one or more substituents selected from Group 2-5A, provided that when they have two or more substituents, then the substituents may be same or different;
- the Group 2-5A consists of halogen and a C1-C6 alkyl group;
- in the Group 2-5A, the C1-C6 alkyl group may be optionally substituted with one or more halogens, provided that when it is substituted with two or more halogens, then the halogens may be same or different;
- R3-5A represents hydrogen, a C1-C6 alkyl group, a (C1-C6 alkoxy)C1-C6 alkyl group, or a benzyl group;
- wherein the C1-C6 alkyl group and the (C1-C6 alkoxy)C1-C6 alkyl group may be optionally substituted with one or more halogens, provided that when they are substituted with two or more halogens, then the halogens may be same or different;
- and the benzyl group may optionally have one or more substituents selected from the group consisting of halogen, a C1-C6 alkyl group, and a C1-C6 alkoxy group, provided that when it has two or more substituents, then the substituents may be same or different;
- R5-5A represents a C1-C6 alkyl group;
- wherein the C1-C6 alkyl group may be optionally substituted with one or more halogens, provided that when it is substituted with two or more halogens, then the halogens may be same or different;
- and
- n represents an integer of 0, 1 or 2.
A compound of the formula (6A):
- wherein the symbols in the formula (6A) are defined as follows:
- G6A represents a 2,4,6-triethylphenyl group, a 2-ethyl-5-(4-chlorophenyl)phenyl group, a 5-ethyl-3-(4-trifluoromethylphenyl)pyrazol-1-yl group, a 1-methylindol-3-yl group or a 2,6-diethyl-4-methylphenyl group;
- and
- X1-6A represents chlorine.
A compound of the formula (8A):
- wherein G8A represents a 2,4,6-triethylphenyl group or a 2,6-diethyl-4-methylphenyl group.
A compound of the formula (9A):
- wherein
- G9A represents a 2,4,6-triethylphenyl group or a 2,6-diethyl-4-methylphenyl group;
- and
- Y9A represents a C1-C6 alkyl group;
- wherein the C1-C6 alkyl group may be optionally substituted with one or more halogens, provided that when it is substituted with two or more halogens, then the halogens may be same or different.
A compound of the formula (12A):
- wherein
- R3-12A represents hydrogen, a C1-C6 alkyl group, or a (C1-C6 alkoxy)C1-C6 alkyl group;
- wherein the C1-C6 alkyl group and the (C1-C6 alkoxy)C1-C6 alkyl group may be optionally substituted with one or more halogens, provided that when they are substituted with two or more halogens, then the halogens may be same or different, and
- G12A represents a phenyl group having a substituent selected from Group R4-12A at 2- position;
- wherein the phenyl group may optionally further have one or more substituents selected from Group R4-12A-a, the substituents may be same or different when the phenyl group has two or more substituents;
- the Group R4-12A consists of halogen, a cyano group, a nitro group, a formyl group, a C1-C6 alkyl group, a C1-C6 alkoxy group, a (C1-C6 alkoxy)C1-C6 alkyl group, a C2-C6 alkenyl group, a C2-C6 alkynyl group, a C3-C6 cycloalkyl group, a C1-C6 alkylthio group, a C1-C6 alkylsulfinyl group, a C1-C6 alkylsulfonyl group;
- a (C1-C6 alkyl)carbonyl group, a (C3-C6 cycloalkyl)carbonyl group, a (C1-C6 alkoxy)carbonyl group, a (C1-C6 alkylamino)carbonyl group, a di(C1-C6 alkyl)aminocarbonyl group, a (C3-C6 cycloalkylamino)carbonyl group, a tri(C1-C6 alkyl)silyl group, a C6-C10 aryl group, and a 5- or 6-membered heteroaryl group;
- in the Group R4-12A, the C1-C6 alkyl group, the C1-C6 alkoxy group, the (C1-C6 alkoxy)C1-C6 alkyl group, the C2-C6 alkenyl group, the C2-C6 alkynyl group, the C3-C6 cycloalkyl group, the C1-C6 alkylthio group, the C1-C6 alkylsulfinyl group, the C1-C6 alkylsulfonyl group, the (C1-C6 alkyl)carbonyl group, the (C3-C6 cycloalkyl)carbonyl group, and the (C1-C6 alkoxy)carbonyl group may be optionally substituted with one or more halogens, provided that when they are substituted with two or more halogens, then the halogens may be same or different;
- and the C6-C10 aryl group and the 5- or 6-membered heteroaryl group may optionally have one or more substituents selected from Group 4-12A, provided that when they have two or more substituents, then the substituents may be same or different;
- the Group 4-12A consists of halogen, a cyano group, a nitro group, a formyl group, a C1-C6 alkyl group, a C1-C6 alkoxy group, a (C1-C6 alkoxy)C1-C6 alkyl group, a C2-C6 alkenyl group, a C2-C6 alkynyl group, a C3-C6 cycloalkyl group, a C1-C6 alkylthio group, a C1-C6 alkylsulfinyl group, a C1-C6 alkylsulfonyl group, a C1-C6 alkylamino group, a di(C1-C6 alkyl)amino group, a C3-C6 cycloalkylamino group, a (C1-C6 alkyl)carbonyl group, a (C3-C6 cycloalkyl)carbonyl group, a (C1-C6 alkoxy)carbonyl group, a (C1-C6 alkylamino)carbonyl group, a di(C1-C6 alkyl)aminocarbonyl group, a (C3-C6 cycloalkylamino)carbonyl group, and a tri(C1-C6 alkyl)silyl group;
- in the Group 4-12A, the C1-C6 alkyl group, the C1-C6 alkoxy group, the (C1-C6 alkoxy)C1-C6 alkyl group, the C2-C6 alkenyl group, the C2-C6 alkynyl group, the C3-C6 cycloalkyl group, the C1-C6 alkylthio group, the C1-C6 alkylsulfinyl group, the C1-C6 alkylsulfonyl group, the (C1-C6 alkyl)carbonyl group, the (C3-C6 cycloalkyl)carbonyl group, and the (C1-C6 alkoxy)carbonyl group may be optionally substituted with one or more halogens, provided that when they are substituted with two or more halogens, then the halogens may be same or different;
- the Group R4-12A-a consists of halogen, a cyano group, a nitro group, a formyl group, a C1-C6 alkyl group, a C1-C6 alkoxy group, a (C1-C6 alkoxy)C1-C6 alkyl group, a C2-C6 alkenyl group, a C2-C6 alkynyl group, a C3-C6 cycloalkyl group, a C1-C6 alkylthio group, a C1-C6 alkylsulfinyl group, a C1-C6 alkylsulfonyl group, a (C1-C6 alkyl)carbonyl group, a (C3-C6 cycloalkyl)carbonyl group, a (C1-C6 alkoxy)carbonyl group, a tri(C1-C6 alkyl)silyl group, a C6-C10 aryl group, and a 5- or 6-membered heteroaryl group;
- in the Group R4-12A-a, the C1-C6 alkyl group, the C1-C6 alkoxy group, the (C1-C6 alkoxy)C1-C6 alkyl group, the C2-C6 alkenyl group, the C2-C6 alkynyl group, the C3-C6 cycloalkyl group, the C1-C6 alkylthio group, the C alkylsulfinyl group, the C1-C6 alkylsulfonyl group, the (C1-C6 alkyl)carbonyl group, the (C3-C6 cycloalkyl)carbonyl group, and the (C1-C6 alkoxy)carbonyl group may be optionally substituted with one or more halogens, provided that when they are substituted with two or more halogens, then the halogens may be same or different;
- and the C6-C10 aryl group and the 5- or 6-membered heteroaryl group may optionally have one or more substituents selected from Group 4-12A-a, provided that when they have two or more substituents, then the substituents may be same or different;
- the Group 4-12A-a consists of halogen, a cyano group, a nitro group, a formyl group, a C1-C6 alkyl group, a C1-C6 alkoxy group, a (C1-C6 alkoxy)C1-C6 alkyl group, a C2-C6 alkenyl group, a C2-C6 alkyl group, a C3-C6 cycloalkyl group, a C1-C6 alkylthio group, a C1-C6 alkylsulfinyl group, a C1-C6 alkylsulfonyl group, a C1-C6 alkylamino group, a di(C1-C6 alkyl)amino group, a C3-C6 cycloalkylamino group, a (C1-C6 alkyl)carbonyl group, a (C3-C6 cycloalkyl)carbonyl group, a (C1-C6 alkoxy)carbonyl group, a (C1-C6 alkylamino)carbonyl group, a di(C1-C6 alkyl)aminocarbonyl group, a (C3-C6 cycloalkylamino)carbonyl group, and a tri(C1-C6 alkyl)silyl group
- in the Group 4-12A-a, the C1-C6 alkyl group, the C1-C6 alkoxy group, the (C1-C6 alkoxy)C1-C6 alkyl group, the C2-C6 alkenyl group, the C2-C6 alkyl group, the C3-C6 cycloalkyl group, the C1-C6 alkylthio group, the C1-C6 alkylsulfinyl group, the C1-C6 alkylsulfonyl group, the (C1-C6 alkyl)carbonyl group, the (C3-C6 cycloalkyl)carbonyl group, and the (C1-C6 alkoxy)carbonyl group may be optionally substituted with one or more halogens, provided that when they are substituted with two or more halogens, then the halogens may be same or different.
A method for producing a compound of the formula (1B):
- which comprises the steps of:
- reacting a compound of the formula (12B):
- with a compound of the formula (20):
- to obtain a compound of the formula (17):
- reacting the compound of the formula (17) with a compound of the formula (18):
- L-R3B (18)
- to obtain a compound of the formula (19):
- decomposing the compound of the formula to obtain a compound of the formula (12C):
- reacting the compound of the formula (12C) with a compound of the formula (7):
- to obtain a compound of the formula (4B):
- reacting the compound of the formula (4B) with a base to obtain a compound of the formula (2B):
- and
- reacting the compound of the formula (2B) with a compound of the formula (3);
- M(OR1)v (3);
- wherein the symbols in the formulae (1B), (2B), (3), (4B), (7), (12B), (12C), (16), (17), (18) and (19) are defined as follows:
- R1 represents hydrogen, a C1-C6 alkyl group or a phenyl group;
- wherein the C1-C6 alkyl group may be optionally substituted with one or more halogens, provided that when it is substituted with two or more halogens, then the halogens may be same or different;
- and the phenyl group may optionally have one or more substituents selected from Group 1, provided that when it has two or more substituents, then the substituents may be same or different;
- the Group 1 consists of halogen, a cyano group, a nitro group, a C1-C6 alkyl group, a C1-C6 alkoxy group, and a (C1-C6 alkoxy)C1-C6 alkyl group;
- in the Group 1, the C1-C6 alkyl group, the C1-C6 alkoxy group and the (C1-C6 alkoxy)C1-C6 alkyl group may be optionally substituted with one or more halogens, provided that when they are substituted with two or more halogens, then the halogens may be same or different;
- R2 represents hydrogen, a C1-C6 alkyl group, a (C1-C6 alkoxy)C1-C6 alkyl group, a C2-C6 alkenyl group, a C2-C6 alkynyl group, a C3-C6 cycloalkyl group, a (C1-C6 alkylthio)C1-C6 alkyl group, a (C1-C6 alkylsulfinyl)C1-C6 alkyl group, a (C1-C6 alkylsulfonyl)C1-C6 alkyl group, a phenyl group, or a 5- or 6-membered heteroaryl group;
- wherein the C1-C6 alkyl group, the (C1-C6 alkoxy)C1-C6 alkyl group, the C2-C6 alkenyl group, the C2-C6 alkynyl group, the C3-C6 cycloalkyl group, the (C1-C6 alkylthio)C1-C6 alkyl group, the (C1-C6 alkylsulfinyl)C1-C6 alkyl group, and the (C1-C6 alkylsulfonyl)C1-C6 alkyl group may be optionally substituted with one or more halogens, provided that when they are substituted with two or more halogens, then the halogens may be same or different;
- and the phenyl group and the 5- or 6-membered heteroaryl group may optionally have one or more substituents selected from Group 2, provided that when they have two or more substituents, then the substituents may be same or different;
- the Group 2 consists of halogen, a cyano group, a nitro group, a formyl group, a C1-C6 alkyl group, a C1-C6 alkoxy group, a (C1-C6 alkoxy)C1-C6 alkyl group, a C2-C6 alkenyl group, a C2-C6 alkynyl group, a C3-C6 cycloalkyl group, a C1-C6 alkylthio group, a C1-C6 alkylsulfinyl group, a C1-C6 alkylsulfonyl group, a C1-C6 alkylamino group, a di(C1-C6 alkyl)amino group, a C3-C6 cycloalkylamino group, a (C1-C6 alkyl)carbonyl group, a (C3-C6 cycloalkyl)carbonyl group, a (C1-C6 alkoxy)carbonyl group, a (C1-C6 alkylamino)carbonyl group, a di(C1-C6 alkyl)aminocarbonyl group, a (C3-C6 cycloalkylamino)carbonyl group, and a tri(C1-C6 alkyl)silyl group;
- in the Group 2, the C1-C6 alkyl group, the C1-C6 alkoxy group, the (C1-C6 alkoxy)C1-C6 alkyl group, the C2-C6 alkenyl group, the C2-C6 alkynyl group, the C3-C6 cycloalkyl group, the C1-C6 alkylthio group, the C1-C6 alkylsulfinyl group, the C1-C6 alkylsulfonyl group, the (C1-C6 alkyl)carbonyl group, the (C3-C6 cycloalkyl)carbonyl group, and the (C1-C6 alkoxy)carbonyl group may be optionally substituted with one or more halogens, provided that when they are substituted with two or more halogens, then the halogens may be same or different;
- R3B represents a C1-C6 alkyl group, a (C1-C6 alkoxy)C1-C6 alkyl group, a C2-C6 alkenyl group, a C2-C6 alkynyl group, a (C1-C6 alkylthio)C1-C6 alkyl group, a C1-C6 alkylsulfonyl group, a (C1-C6 alkyl)carbonyl group, a (C1-C6 alkoxy)carbonyl group, a di(C1-C6 alkyl)aminocarbonyl group, a benzyl group, or a phenylsulfonyl group;
- wherein the C1-C6 alkyl group, the (C1-C6 alkoxy)C1-C6 alkyl group, the C2-C6 alkenyl group, the C2-C6 alkynyl group, the (C1-C6 alkylthio)C1-C6 alkyl group, the C1-C6 alkylsulfonyl group, the (C1-C6 alkyl)carbonyl group, and the (C1-C6 alkoxy)carbonyl group may be optionally substituted with one or more halogens, provided that when they are substituted with two or more halogens, then the halogens may be same or different;
- and the benzyl group, and the phenylsulfonyl group may optionally have one or more substituents selected from Group 3B, provided that when they have two or more substituents, then the substituents may be same or different,
- the Group 3B consists of halogen, a C1-C6 alkyl group, a C1-C6 alkoxy group, and a (C1-C6 alkoxy)C1-C6 alkyl group;
- in the Group 3B, the C1-C6 alkyl group, the C1-C6 alkoxy group, and the (C1-C6 alkoxy)C1-C6 alkyl group may be optionally substituted with one or more halogens, provided that when they are substituted with two or more halogens, then the halogens may be same or different;
- R5 represents a C1-C6 alkyl group or a phenyl group;
- wherein the C1-C6 alkyl group may be optionally substituted with one or more halogens, provided that when it is substituted with two or more halogens, then the halogens may be same or different;
- and the phenyl group may optionally have one or more substituents selected from Group 5, provided that when it has two or more substituents, then the substituents may be same or different;
- the Group 5 consists of halogen, a C1-C6 alkyl group, and a C1-C6 alkoxy group;
- in the Group 5, the C1-C6 alkyl group and the C1-C6 alkoxy group may be optionally substituted with one or more halogens, provided that when they are substituted with two or more halogens, then the halogens may be same or different;
- GB represents a phenyl group;
- wherein the phenyl group may optionally have one or more substituents selected from Group R4-B, provided that when it has two or more substituents, then the substituents may be same or different;
- the Group R4-B consists of halogen, a cyano group, a nitro group, a formyl group, a C1-C6 alkyl group, a C1-C6 alkoxy group, a (C1-C6 alkoxy)C1-C6 alkyl group, a C2-C6 alkenyl group, a C2-C6 all group, a C3-C6 cycloalkyl group, a C1-C6 alkylthio group, a C1-C6 alkylsulfinyl group, a C1-C6 alkylsulfonyl group, a C1-C6 alkylamino group, a di(C1-C6 alkyl)amino group, a C3-C6 cycloalkylamino group, a (C1-C6 alkyl)carbonyl group, a (C3-C6 cycloalkyl)carbonyl group, a (C1-C6 alkoxy)carbonyl group, a (C1-C6 alkylamino)carbonyl group, a di(C1-C6 alkyl)aminocarbonyl group, a (C3-C6 cycloalkylamino)carbonyl group, a tri(C1-C6 alkyl)silyl group, a C6-C10 aryl group, and a 5- or 6-membered heteroaryl group;
- in the Group R4-B, the C1-C6 alkyl group, the C1-C6 alkoxy group, the (C1-C6 alkoxy)C1-C6 alkyl group, the C2-C6 alkenyl group, the C2-C6 alkynyl group, the C3-C6 cycloalkyl group, the C1-C6 alkylthio group, the C1-C6 alkylsulfinyl group, the C1-C6 alkylsulfonyl group, the (C1-C6 alkyl)carbonyl group, the (C3-C6 cycloalkyl)carbonyl group, and the (C1-C6 alkoxy)carbonyl group may be optionally substituted with one or more halogens, provided that when they are substituted with two or more halogens, then the halogens may be same or different;
- and the C6-C10 aryl group and the 5- or 6-membered heteroaryl group may optionally have one or more substituents selected from Group 4-B, provided that when they have two or more substituents, then the substituents may be same or different;
- the Group 4-B consists of halogen, a cyano group, a nitro group, a formyl group, a C1-C6 alkyl group, a C1-C6 alkoxy group, a (C1-C6 alkoxy)C1-C6 alkyl group, a C2-C6 alkenyl group, a C2-C6 alkynyl group, a C3-C6 cycloalkyl group, a C1-C6 alkylthio group, a C1-C6 alkylsulfinyl group, a C1-C6 alkylsulfonyl group, a C1-C6 alkylamino group, a di(C1-C6 alkyl)amino group, a C3-C6 cycloalkylamino group, a (C1-C6 alkyl)carbonyl group, a (C3-C6 cycloalkyl)carbonyl group, a (C1-C6 alkoxy)carbonyl group, a (C1-C6 alkylamino)carbonyl group, a di(C1-C6 alkyl)aminocarbonyl group, a (C3-C6 cycloalkylamino)carbonyl group, and a tri(C1-C6 alkyl)silyl group;
- in the Group 4-B, the C1-C6 alkyl group, the C1-C6 alkoxy group, the (C1-C6 alkoxy)C1-C6 alkyl group, the C2-C6 alkenyl group, the C2-C6 alkynyl group, the C3-C6 cycloalkyl group, the C1-C6 alkylthio group, the C1-C6 alkylsulfinyl group, the C1-C6 alkylsulfonyl group, the (C1-C6 alkyl)carbonyl group, the (C3-C6 cycloalkyl)carbonyl group, and the (C1-C6 alkoxy)carbonyl group may be optionally substituted with one or more halogens;
- provided that when they are substituted with two or more halogens, then the halogens may be same or different:
- n represents an integer of 0, 1 or 2;
- V represents an integer of 1 or 2
- M represents an alkali metal when V is an integer of 1, and M represents an alkali earth metal when V is an integer of 2;
- R10 and R11 may be same or different, and each represents hydrogen, a C1-C6 alkyl group, a C3-C6 cycloalkyl group or a phenyl group, or R10 and R11 may be combined to form 5- or 6-membered cyclic group with a carbon atom which is bonded with R10 and R11,
- wherein the C1-C6 alkyl group and the C3-C6 cycloalkyl group may be optionally substituted with one or more halogens, provided that when they are substituted with two or more halogens, then the halogens may be same or different;
- and the phenyl group may optionally have one or more substituents selected from Group 10, provided that when it has two or more substituents, then the substituents may be same or different;
- the Group 10 consists of halogen, a C1-C6 alkyl group and a C1-C6 alkoxy group;
- and
- L represents halogen a C1-C6 alkylsulfonyloxy group or a C1-C6 alkoxysulfonyloxy group.
Dependencies are inferred from the claim text.