Tetrazoyloxime derivative and plant disease control agent

A tetrazoyloxime derivative represented by formula (1):

• wherein X represents a halogen atom, a C1-8 alkyl group, a C1-8 alkoxy group, a cyano group, a C1-8 alkylsulfonyl group, a nitro group, a C1-8 haloalkyl group, or an unsubstituted or substituted aryl group;
• n1 represents any one of integers of 0 to 5, and
• when n1 is 2 or more, X(s) may be the same or different with each other;
• A represents a tetrazoyl group represented by formula (2):
• (in which Y represents a C1-8 alkyl group), or a tetrazoyl group represented by formula (3):
• (in which Y is the same as defined above);
• and
• Het represents a pyridyl group represented by formula (4):
• (in which R represents a halogen atom, a cyano group, a nitro group, a hydroxyl group, a thiol group, a formyl group, a carboxyl group, an unsubstituted or substituted amino group, an unsubstituted or substituted C1-8 alkyl group, an unsubstituted or substituted C2-8 alkenyl group, an unsubstituted or substituted C2-8 alkynyl group, an unsubstituted or substituted aryl group, an unsubstituted or substituted heterocyclic group, OR1, S(O)mR1, COR1, or CO2R1, R1 represents an unsubstituted or substituted amino group, an unsubstituted or substituted C1-8 alkyl group, an unsubstituted or substituted C3-8 cycloalkyl group, an unsubstituted or substituted C2-8 alkenyl group, an unsubstituted or substituted C2-8 alkynyl group, or an unsubstituted or substituted aryl group,
• m represents any one of integers of 0 to 2,
• n2 represents any one of integers of 0 to 3, and
• when n2 is 2 or more, plural R(s) may be the same or different from each other,
• when n2 is 0, Z represents a group represented by formula:
• Q1C(═O)NH— (in which Q1 represents a C1-8 haloalkyl group, a C2-8 haloalkenyl group, a C2-8 alkynyl group, a C2-8 haloalkynyl group, a C1-8 haloalkoxy group, a C2-8 alkenyloxy group, a C2-8 haloalkenyloxy group, a C2-8 alkynyloxy group, a C2-8 haloalkynyloxy group, a C1-8 alkoxy group substituted with an alkoxycarbonylamino group, a C1-8 alkoxy group substituted with a C3-8 cycloalkyl group, a C1-8 branched alkoxy group substituted with an unsubstituted aryl group, a C1-8 alkoxy group substituted with substituted aryl, a C1-8 alkoxy group substituted with an unsubstituted or substituted heterocyclic group, a C1-8 alkoxy group substituted with an unsubstituted or substituted C1-8 alkoxy group, a C1-8 alkoxy group substituted with an unsubstituted or substituted aryloxy group, an C1-8 alkoxy group substituted with an unsubstituted or substituted aralkyloxy group, a C2-8 alkynyloxy group substituted with an unsubstituted or substituted aryl group, a C1-8 alkoxy group substituted with an unsubstituted or substituted C1-8 alkylthio group, a C1-8 alkoxy group substituted with an unsubstituted or substituted arylthio group, a C1-8 alkoxy group substituted with an unsubstituted or substituted C1-8 alkylsulfinyl group, a C1-8 alkoxy group substituted with an unsubstituted or substituted arylsulfinyl group, a C1-8 alkoxy group substituted with an unsubstituted or substituted C1-8 alkylsulfonyl group, a C1-8 alkoxy group substituted with an unsubstituted or substituted arylsulfonyl group, a C1-8 alkoxy group substituted with an amino group which is unsubstituted or substituted with an (unsubstituted or substituted alkyl group), a C1-8 alkoxy group which is substituted with an amino group substituted with an (unsubstituted or substituted aralkyl group), an unsubstituted or substituted aryloxy group, a C1-8 alkyl group substituted with a carboxyl group, a C1-8 alkyl group substituted with an amino group which is unsubstituted or substituted with an (unsubstituted or substituted aralkyl group), a C1-8 alkyl group substituted with an amino group which is substituted with an (unsubstituted or substituted alkyl group), a C1-8 alkyl group substituted with an unsubstituted or substituted aryloxy group, a C1-8 alkyl group substituted with an acyl group, or a C1-8 alkyl group substituted with an unsubstituted or substituted heterocyclicoxy group),
• when n2 is 1 and R is a halogen atom, Z represents a hydrogen atom, an amino group, or a group represented by formula:
• Q2C(═O)NH— (in which Q2 represents a hydrogen atom, a C1-8 haloalkyl group, a C2-8 alkenyl group, a C2-8 haloalkenyl group, a C2-8 alkynyl group, a C2-8 haloalkynyl group, a C1-8 alkoxy group, a C1-8 haloalkoxy group, a C2-8 alkenyloxy group, a C2-8 haloalkenyloxy group, a C2-8 alkynyloxy group, a C2-8 haloalkynyloxy group, a C3-8 cycloalkyl group, a C3-8 cycloalkyloxy group, a C1-8 alkylamino group, a C1-8 alkoxy group substituted with an unsubstituted or substituted amino group, a C1-8 alkoxy group substituted with a C3-8 cycloalkyl group, an unsubstituted or substituted aralkyloxy group, a C1-8 alkoxy group substituted with an unsubstituted or substituted heterocyclic group, a C1-8 alkoxy group substituted with an unsubstituted or substituted C1-8 alkoxy group, a C1-8 alkoxy group substituted with an unsubstituted or substituted aryloxy group, a C1-8 alkoxy group substituted with an unsubstituted or substituted aralkyloxy group, a C2-8 alkynyloxy group substituted with an unsubstituted or substituted aryl group, a C1-8 alkoxy group substituted with an unsubstituted or substituted C1-8 alkylthio group, a C1-8 alkoxy group substituted with an unsubstituted or substituted arylthio group, a C1-8 alkoxy group substituted with an unsubstituted or substituted C1-8 alkylsulfinyl group, a C1-8 alkoxy group substituted with an unsubstituted or substituted arylsulfinyl group, a C1-8 alkoxy group substituted with an unsubstituted or substituted C1-8 alkylsulfonyl group, C1-8 alkoxy group substituted with an unsubstituted or substituted arylsulfonyl group, an unsubstituted or substituted aryloxy group, a C1-8 alkyl group substituted with a carboxyl group, a C1-8 alkyl group substituted with an unsubstituted or substituted amino group, a C1-8 alkyl group substituted with an unsubstituted or substituted aryloxy group, a C1-8 alkyl group substituted with an unsubstituted or substituted C1-8 alkylthio group, a C1-8 alkyl group substituted with an unsubstituted or substituted alkoxy group, a C1-8 alkyl group substituted with an acyl group, or a C1-8 alkyl group substituted with an unsubstituted or substituted heterocyclicoxy group),
• when n2 is 1 or more and at least one R is a cyano group, a nitro group, a hydroxyl group, a thiol group, a formyl group, a carboxyl group, an unsubstituted or substituted amino group, an unsubstituted or substituted C1-8 alkyl group, an unsubstituted or substituted C2-8 alkenyl group, an unsubstituted or substituted C2-8 alkynyl group, an unsubstituted or substituted aryl group, an unsubstituted or substituted heterocyclic group, OR1, S(O)mR1, COR1, or CO2R1, or when n2 is 2 or more and at least two R(s) are halogen atoms, Z represents a hydrogen atom, an amino group, or a group represented by formula:
• Q3C(═O)NH— (in which Q3 represents a hydrogen atom, a C1-8 alkyl group, a C1-8 haloalkyl group, a C2-8 alkenyl group, a C2-8 haloalkenyl group, a C2-8 alkynyl group, a C2-8 haloalkynyl group, a C1-8 alkoxy group, a C1-8 haloalkoxy group, a C2-8 alkenyloxy group, a C2-8 haloalkenyloxy group, a C2-8 alkynyloxy group, a C2-8 haloalkynyloxy group, a C3-8 cycloalkyl group, a C3-8 cycloalkyloxy group, a C1-8 alkylamino group, a C1-8 alkoxy group substituted with an unsubstituted or substituted amino group, a C1-8 alkoxy group substituted with a C3-8 cycloalkyl group, an unsubstituted or substituted aralkyloxy group, a C1-8 alkoxy group substituted with an unsubstituted or substituted heterocyclic group, a C1-8 alkoxy group substituted with an unsubstituted or substituted C1-8 alkoxy group, a C1-8 alkoxy group substituted with an unsubstituted or substituted aryloxy group, a C1-8 alkoxy group substituted with an unsubstituted or substituted aralkyloxy group, a C2-8 alkynyloxy group substituted with an unsubstituted or substituted aryl group, a C1-8 alkoxy group substituted with an unsubstituted or substituted C1-8 alkylthio group, a C1-8 alkoxy group substituted with a substituted or unsubstituted arylthio group, a C1-8 alkoxy group substituted with an unsubstituted or substituted C1-8 alkylsulfinyl group, a C1-8 alkoxy group substituted with an unsubstituted or substituted arylsulfinyl group, a C1-8 alkoxy group substituted with an unsubstituted or substituted C1-8 alkylsulfonyl group, a C1-8 alkoxy group substituted with an unsubstituted or substituted arylsulfonyl group, an unsubstituted or substituted aryloxy group, a C1-8 alkyl group substituted with a carboxyl group, a C1-8 alkyl group substituted with an unsubstituted or substituted amino group, a C1-8 alkyl group substituted with an unsubstituted or substituted aryloxy group, a C1-8 alkyl group substituted with an unsubstituted or substituted C1-8 alkylthio group, a C1-8 alkyl group substituted with an unsubstituted or substituted alkoxy group, an alkyl group substituted with an acyl group, or a C1-8 alkyl group substituted with an unsubstituted or substituted heterocyclicoxy group), or a thiazoyl group represented by formula (5):
• (in which R11 represents a hydrogen atom, a halogen atom, a cyano group, a nitro group, a hydroxyl group, a thiol group, a formyl group, a carboxyl group, an unsubstituted or substituted amino group, an unsubstituted or substituted C1-8 alkyl group, an unsubstituted or substituted C2-8 alkenyl group, an unsubstituted or substituted C2-4 alkynyl group, an unsubstituted or substituted aryl group, an unsubstituted or substituted heterocyclic group, OR1, S(O)mR1, COR1, or CO2R1,
• R1 is the same as defined above,
• when R11 is a hydrogen atom, Z11 represents a group represented by formula:
• Q1C(═O)NH— (in which Q1 is the same as defined above),
• when R11 is a halogen atom, Z11 represents a hydrogen atom, an amino group, or a group represented by formula:
• Q2C(═O)NH— (in which Q2 is the same as defined above), and when R11 is a cyano group, a nitro group, a hydroxyl group, a thiol group, a formyl group, a carboxyl group, an unsubstituted or substituted amino group, an unsubstituted or substituted C1-8 alkyl group, an unsubstituted or substituted C2-8 alkenyl group, an unsubstituted or substituted C2-8 alkynyl group, an unsubstituted or substituted aryl group, an unsubstituted or substituted heterocyclic group, OR1, S(O)mR1, COR1, or CO2R1, Z11 represents a hydrogen atom, an amino group, or a group represented by formula:
• Q3C(═O)NH— (in which Q3 is the same as defined above), and a salt thereof.