Plant disease control agent, and plant disease control method

A plant disease control method which comprises applying an effective amount of an amide compound represented by the formula (1) to plants or soil:

• wherein
• X1 represents a fluorine atom or a methoxy group,
• X2 represents a hydrogen atom, a halogen atom, a C1-C4 alkyl group, a C2-C4 alkenyl group, a C2-C4 alkynyl group, a C1-C4 haloalkyl group, a C1-C4 alkoxy group, a C1-C4 alkylthio group, a C1-C4 hydroxyalkyl group, a nitro group, a cyano group, a formyl group, an NR1R2 group, a CO2R3 group or a CONR4R5 group, or a phenyl group optionally substituted with at least one member selected from the group consisting of a methyl group, a halogen atom, a cyano group and a nitro group,
• Z1 represents an oxygen atom or a sulfur atom,
• A1 represents a single bond, —CH2—, —CH(CH3)—, —C(CH3)2—, —CH(CH2CH3)—, or methylene substituted with at least one member selected from the group consisting of a C1-C3 haloalkyl group, a C2-C4 alkenyl group, a C2-C4 alkynyl group, a cyano group and a C2-C5 alkoxycarbonyl group,
• G1 represents a CR6R7R8 group (provided that the aforementioned A1 is not a single bond when G1 is a CR6R7R8 group), a C3-C6 cycloalkyl group optionally substituted with at least one member selected from the group [a-1] shown below, a C3-C6 cycloalkenyl group optionally substituted with at least one member selected from the group [a-1] shown below, a C3-C6 cycloalkyl group optionally substituted with at least one member selected from the group [a-1] shown below wherein one methylene forming ring is replaced by a carbonyl group, or a C3-C6 hydroxyiminocycloalkyl group optionally substituted with at least one member selected from the group [a-1] shown below,
• R1 and R2 independently represent a hydrogen atom, a C1-C4 alkyl group, a C3-C4 alkenyl group, a C3-C4 alkynyl group, a C2-C4 haloalkyl group, a C2-C5 alkylcarbonyl group, a C2-C5 alkoxycarbonyl group or a C1-C4 alkylsulfonyl group,
• R3 represents a C1-C4 alkyl group, a C3-C4 alkenyl group or a C3-C4 alkynyl group,
• R4 represents a hydrogen atom, a C1-C4 alkyl group, a C3-C4 alkenyl group, a C3-C4 alkynyl group, a C2-C4 haloalkyl group, a C2-C5 alkylcarbonyl group, a C2-C5 alkoxycarbonyl group or a C1-C4 alkylsulfonyl group,
• R5 represents a hydrogen atom, a C1-C4 alkyl group, a C3-C4 alkenyl group, a C3-C4 alkynyl group or a C2-C4 haloalkyl group,
• R6 and R7 independently represent a C1-C4 alkyl group,
• R8 represents a hydrogen atom, a C1-C4 alkyl group, a C2-C4 alkenyl group, a C2-C4 alkynyl group, a cyano group, a carboxyl group, a C2-C5 alkoxycarbonyl group, a halogen atom, a hydroxyl group, a C1-C6 alkoxy group, a C3-C6 alkenyloxy group, a C1-C6 haloalkyl group, a C2-C6 haloalkoxy group, a C1-C3 alkylthio group, a C1-C6 hydroxyalkyl group, a C2-C4 alkylcarbonyloxy group, a (C1-C3 alkylamino)C1-C6 alkyl group, a (di(C1-C3 alkyl)amino)C1-C6 alkyl group, a mercapto group, a carbamoyl group, a C2-C6 cyanoalkyl group, a C1-C3 alkylsulfonyl group or an NR9R10 group, in which R9 and R10 independently represent a hydrogen atom, a C1-C4 alkyl group, a C2-C5 alkylcarbonyl group, a C2-C5 alkoxycarbonyl group or a C1-C4 alkylsulfonyl group, and
• the group [a-1]:
• a halogen atom, a C1-C4 alkyl group, a C2-C4 alkenyl group, a C2-C4 alkynyl group, a hydroxyl group, a cyano group, carboxyl group, a C2-C5 alkoxycarbonyl group, a C1-C6 alkoxy group, a C3-C6 alkenyloxy group, a C1-C6 haloalkyl group, a C1-C6 haloalkoxy group, a phenyl group, a benzyl group, a C1-C3 alkylthio group, a C1-C3 alkylidene group which forms a double bond with a ring-forming carbon atom, a C1-C6 hydroxyalkyl group, a C2-C4 alkylcarbonyloxy group, a (C1-C3 alkylamino)C1-C6 alkyl group, a (di(C1-C3 alkyl)amino)C1-C6 alkyl group, a mercapto group, a carbamoyl group, a formyl group, a C2-C6 cyanoalkyl group, a C1-C3 alkylsulfonyl group, a phenoxy group and an NR9R10 group, in which R9 and R10 are as defined above.

Use of an amide compound represented by the formula (1):

• wherein
• X1 represents a fluorine atom or a methoxy group,
• X2 represents a hydrogen atom, a halogen atom, a C1-C4 alkyl group, a C2-C4 alkenyl group, a C2-C4 alkynyl group, a C1-C4 haloalkyl group, a C1-C4 alkoxy group, a C1-C4 alkylthio group, a C1-C4 hydroxyalkyl group, a nitro group, a cyano group, a formyl group, an NR1R2 group, a CO2R3 group or a CONR4R5 group, or a phenyl group optionally substituted with at least one member selected from the group consisting of a methyl group, a halogen atom, a cyano group and a nitro group,
• Z1 represents an oxygen atom or a sulfur atom,
• A1 represents a single bond, —CH2—, —CH(CH3)—, —C(CH3)2—, —CH(CH2CH3)—, or methylene substituted with at least one member selected from the group consisting of a C1-C3 haloalkyl group, a C2-C4 alkenyl group, a C2-C4 alkynyl group, a cyano group and a C2-C5 alkoxycarbonyl group,
• G1 represents a CR6R7R8 group (provided that the aforementioned A1 is not a single bond when G1 is a CR6R7R8 group), a C3-C6 cycloalkyl group optionally substituted with at least one member selected from the group [a-1] shown below, a C3-C6 cycloalkenyl group optionally substituted with at least one member selected from the group [a-1] shown below, a C3-C6 cycloalkyl group optionally substituted with at least one member selected from the group [a-1] shown below wherein one methylene forming ring is replaced by a carbonyl group, or a C3-C6 hydroxyiminocycloalkyl group optionally substituted with at least one member selected from the group [a-1] shown below,
• R1 and R2 independently represent a hydrogen atom, a C1-C4 alkyl group, a C3-C4 alkenyl group, a C3-C4 alkynyl group, a C2-C4 haloalkyl group, a C2-C5 alkylcarbonyl group, a C2-C5 alkoxycarbonyl group or a C1-C4 alkylsulfonyl group,
• R3 represents a C1-C4 alkyl group, a C3-C4 alkenyl group or a C3-C4 alkynyl group,
• R4 represents a hydrogen atom, a C1-C4 alkyl group, a C3-C4 alkenyl group, a C3-C4 alkynyl group, a C2-C4 haloalkyl group, a C2-C5 alkylcarbonyl group, a C2-C5 alkoxycarbonyl group or a C1-C4 alkylsulfonyl group,
• R5 represents a hydrogen atom, a C1-C4 alkyl group, a C3-C4 alkenyl group, a C3-C4 alkynyl group or a C2-C4 haloalkyl group,
• R6 and R7 independently represent a C1-C4 alkyl group,
• R8 represents a hydrogen atom, a C1-C4 alkyl group, a C2-C4 alkenyl group, a C2-C4 alkynyl group, a cyano group, a carboxyl group, a C2-C5 alkoxycarbonyl group, a halogen atom, a hydroxyl group, a C1-C6 alkoxy group, a C3-C6 alkenyloxy group, a C1-C6 haloalkyl group, a C2-C6 haloalkoxy group, a C1-C3 alkylthio group, a C1-C6 hydroxyalkyl group, a C2-C4 alkylcarbonyloxy group, a (C1-C3 alkylamino)C1-C6 alkyl group, a (di(C1-C3 alkyl)amino)C1-C6 alkyl group, a mercapto group, a carbamoyl group, a C2-C6 cyanoalkyl group, a C1-C3 alkylsulfonyl group or an NR9R10 group, in which R9 and R10 independently represent a hydrogen atom, a C1-C4 alkyl group, a C2-C5 alkylcarbonyl group, a C2-C5 alkoxycarbonyl group or a C1-C4 alkylsulfonyl group, and
• the group [a-1]:
• a halogen atom, a C1-C4 alkyl group, a C2-C4 alkenyl group, a C2-C4 alkynyl group, a hydroxyl group, a cyano group, carboxyl group, a C2-C5 alkoxycarbonyl group, a C1-C6 alkoxy group, a C3-C6 alkenyloxy group, a C1-C6 haloalkyl group, a C1-C6 haloalkoxy group, a phenyl group, a benzyl group, a C1-C3 alkylthio group, a C1-C3 alkylidene group which forms a double bond with a ring-forming carbon atom, a C1-C6 hydroxyalkyl group, a C2-C4 alkylcarbonyloxy group, a (C1-C3 alkylamino)C1-C6 alkyl group, a (di(C1-C3 alkyl)amino)C1-C6 alkyl group, a mercapto group, a carbamoyl group, a formyl group, a C2-C6 cyanoalkyl group, a C1-C3 alkylsulfonyl group, a phenoxy group and an NR9R10 group, in which R9 and R10 are as defined above, for controlling plant diseases by applying it to plants or soil.

A 3,5-difluoro-4-methoxybenzamide compound represented by the formula (A):

• wherein
• Z2 represents an oxygen atom or a sulfur atom,
• A2 represents a single bond, —CH2—, —CH(CH3)—, —C(CH3)2—, —CH(CH2CH3)—, or methylene substituted with at least one member selected from the group consisting of a C1-C3 haloalkyl group, a C2-C4 alkenyl group, a C2-C4 alkynyl group, a cyano group and a C2-C5 alkoxycarbonyl group, G2 is a CR26R27R28 group (provided that the aforementioned A2 is not a single bond when G2 is a CR26R27R28 group), a C3-C6 cycloalkyl group optionally substituted with at least one member selected from the group [a-2] shown below, a C3-C6 cycloalkenyl group optionally substituted with at least one member selected from the group [a-2] shown below, a C3-C6 cycloalkyl group optionally substituted with at least one member selected from the group [a-2] shown below wherein one methylene forming ring is replaced by a carbonyl group, or a C3-C6 hydroxyiminocycloalkyl group optionally substituted with at least one member selected from the group [a-2] shown below,
• R26 and R27 independently represent a C1-C4 alkyl group,
• R28 represents a hydrogen atom, a C1-C4 alkyl group, a C2-C4 alkenyl group, a C2-C4 alkynyl group, a cyano group, a carboxyl group, a C2-C5 alkoxycarbonyl group, a halogen atom, a hydroxyl group, a C1-C6 alkoxy group, a C3-C6 alkenyloxy group, a C1-C6 haloalkyl group, a C2-C6 haloalkoxy group, a C1-C3 alkylthio group, a C1-C6 hydroxyalkyl group, a C2-C4 alkylcarbonyloxy group, a (C1-C3 alkylamino)C1-C6 alkyl group, a (di(C1-C3 alkyl)amino)C1-C6 alkyl group, a mercapto group, a carbamoyl group, a C2-C6 cyanoalkyl group, a C1-C3 alkylsulfonyl group, or an NR29R30 group, in which R29 and R30 independently represent a hydrogen atom, a C1-C4 alkyl group, a C2-C5 alkylcarbonyl group, a C2-C5 alkoxycarbonyl group or a C1-C4 alkylsulfonyl group, and
• the group [a-2]:
• a halogen atom, a C1-C4 alkyl group, a C2-C4 alkenyl group, a C2-C4 alkynyl group, a hydroxyl group, a cyano group, a carboxyl group, a C2-C5 alkoxycarbonyl group, a C1-C6 alkoxy group, a C3-C6 alkenyloxy group, a C1-C6 haloalkyl group, a C1-C6 haloalkoxy group, a phenyl group, a benzyl group, a C1-C3 alkylthio group, a C1-C3 alkylidene group which forms a double bond with a ring-forming carbon atom, a C1-C6 hydroxyalkyl group, a C2-C4 alkylcarbonyloxy group, a (C1-C3 alkylamino)C1-C6 alkyl group, a (di(C1-C3 alkyl)amino)C1-C6 alkyl group, a mercapto group, a carbamoyl group, a formyl group, a C2-C6 cyanoalkyl group, a C1-C3 alkylsulfonyl group, a phenoxy group, and an NR29R30 group, in which R29 and R30 are as defined above.