METHOD OF CONTROLLING SOYBEAN RUST FUNGUS HAVING RESISTANCE TO QoI FUNGICIDE

A method for controlling a soybean rust fungus having an amino acid substitution of F129L in a mitochondrial cytochrome b protein, which comprises applying an effective amount of a compound represented by formula (I)

• [wherein:
• R1 represents a C1-C4 alkyl group, a C1-C4 alkoxy group {wherein said C1-C4 alkyl group and said C1-C4 alkoxy group are optionally substituted with one or more halogen atom(s)}, a cyano group, a nitro group, a halogen atom, or a hydroxy group;
• n represents 0, 1, or 2;
• when n represents 2, two R1 may be identical to or different from each other;
• Q represents a group represented by Q1 or a group represented by Q2;
• • represents the binding site to the rest of molecule;
• X1 represents —C(H)═ or —N═;
• X2 represents —C(O)OCH3, —C(O)NHCH3, or a 5,6-dihydro-1,4,2-dioxazin-3-yl group;
• X3 represents a C1-C3 chain hydrocarbon group, a cyclopropyl group, a C1-C3 alkoxy group {wherein said C1-C3 chain hydrocarbon group, said cyclopropyl group, and said C1-C3 alkoxy group are optionally substituted with one or more halogen atom(s)}, or a halogen atom;
• J represents a group represented by J1 or a group represented by J2;
• # represents the binding position to E;
• Y1 represents an oxygen atom, a sulfur atom, —N(R2)—, *—C(R3)═C(R4)—, or *-N=C(R5)-;
• * represents the binding position to the carbon atom bound to E;
• Y2 represents ═C(R6)— or ═N—;
• Y3 represents ═C(R7)— or ═N—;
• Y4 represents an oxygen atom, a sulfur atom, or —N(R8)—;
• R2 and R8 are identical to or different from each other, and each represent a C1-C3 chain hydrocarbon group, a cyclopropyl group {wherein said C1-C3 chain hydrocarbon group and said cyclopropyl group are optionally substituted with one or more halogen atom(s)}, or a hydrogen atom;
• R3, R4, R5, R6, and R7 are identical to or different from each other, and each represent a C1-C4 alkyl group, a C1-C4 alkoxy group {wherein said C1-C4 alkyl group and said C1-C4 alkoxy group are optionally substituted with one or more halogen atom(s)}, a cyano group, a nitro group, a halogen atom, a hydroxy group, or a hydrogen atom;
• E represents a C1-C6 chain hydrocarbon group optionally substituted with one or more substituent(s) selected from Group A, a C3-C10 alicyclic hydrocarbon group, a 3-10 membered nonaromatic heterocyclic group {wherein said C3-C10 alicyclic hydrocarbon group and said 3-10 membered nonaromatic heterocyclic group are optionally substituted with one or more substituent(s) selected from Group B}, a C6-C10 aryl group, a 5-10 membered aromatic heterocyclic group {wherein said C6-C10 aryl group and said 5-10 membered aromatic heterocyclic group are optionally substituted with one or more substituent(s) selected from Group D}, R9—L1—CH2—, R10R11C═N—O—CH2—, R12O—N═C(R13)—C(R14)═N—O—CH2—, R15C(O)—C(R16)═N—O—CH2—, R17R18N—C(S)—O—CH2-, R19N═C(R20)—S—CH2—, R21N═C(SR22)—S—CH2—, R23O—N═C(R24)—S—CH2—, R25O—N═C(SR26)—S—CH2—, R27O—N═C(R28)—, R29R30C═N—N═C(R31)—, R32R33N—N═C(R34)—, R35—N═C(R36)—, R37SC(R38)═N—, R39SC(SR40)═N—, R41L2-, R43C(O)O—, R44OC(O)O—, R45R46NC(O)O-, R47R48NC(S)O-, R49S(O)2O—, R50R51NS(O)2O-, a cyano group, a nitro group, a hydroxy group, or a halogen atom;
• L1 and L2 are identical to or different from each other, and each represent an oxygen atom or a sulfur atom;
• R9 represents a C6-C10 aryl group or a 5-10 membered aromatic heterocyclic group {wherein said C6-C10 aryl group and said 5-10 membered aromatic heterocyclic group are optionally substituted with one or more substituent(s) selected from Group D};
• R12, R15, R17, R19, R21, R23, R25, R29, R32, R37, R39, R43, R44, R45, R47, R49, and > R50 are identical to or different from each other, and each represent a C1-C6 chain hydrocarbon group optionally substituted with one or more substituent(s) selected from Group F, a C3-C10 alicyclic hydrocarbon group optionally substituted with one or more substituent(s) selected from Group B, a C6-C10 aryl group, or a 5-10 membered aromatic heterocyclic group {wherein said C6-C10 aryl group and said 5-10 membered aromatic heterocyclic group are optionally substituted with one or more substituent(s) selected from Group C};
• R10, R27, R35, and R41 are identical to or different from each other, and each represent a C1-C6 chain hydrocarbon group optionally substituted with one or more substituent(s) selected from Group A, a C3-C10 alicyclic hydrocarbon group, a 3-10 membered nonaromatic heterocyclic group {wherein said C3-C10 alicyclic hydrocarbon group and said 3-10 membered nonaromatic heterocyclic group are optionally substituted with one or more substituent(s) selected from Group B}, a C6-C10 aryl group, or a 5-10 membered aromatic heterocyclic group {wherein said C6-C10 aryl group and said 5-10 membered aromatic heterocyclic group are optionally substituted with one or more substituent(s) selected from Group D};
• R11, R13, R14, R16, R18, R20, R22, R24, R26, R28, R30, R31, R33, R34, R36, R38, R40, R46, R48, and R51 are identical to or different from each other, and each represent a C1-C3 chain hydrocarbon group optionally substituted with one or more halogen atom(s), a cyclopropyl group, or a hydrogen atom;
• R10 and R11 are optionally combined with the carbon atom to which they are attached to form a C3-C10 alicyclic hydrocarbon group or a 3-10 membered nonaromatic heterocyclic group {wherein said C3-C10 alicyclic hydrocarbon group and said 3-10 membered nonaromatic heterocyclic group are optionally substituted with one or more substituent(s) selected from Group B};
• and
• R29 and R30 are optionally combined with the carbon atom to which they are attached to form a C3-C10 alicyclic hydrocarbon group or a 3-10 membered nonaromatic heterocyclic group {wherein said C3-C10 alicyclic hydrocarbon group and said 3-10 membered nonaromatic heterocyclic group are optionally substituted with one or more substituent(s) selected from Group B};
• Group A:
• a group consisting of a C3-C10 alicyclic hydrocarbon group, a 3-10 membered nonaromatic heterocyclic group {wherein said C3-C10 alicyclic hydrocarbon group and said 3-10 membered nonaromatic heterocyclic group are optionally substituted with one or more substituent(s) selected from Group B}, a C1-C4 alkoxy group, a C1-C4 alkylthio group {wherein said C1-C4 alkoxy group and said C1-C4 alkylthio group are optionally substituted with one or more substituent(s) selected from Group F}, a halogen atom, a cyano group, a nitro group, a hydroxy group, an oxo group, a thioxo group, a C6-C10 aryl group, and a 5-10 membered aromatic heterocyclic group {wherein said C6-C10 aryl group and said 5-10 membered aromatic heterocyclic group are optionally substituted with one or more substituent(s) selected from Group D};
• Group B:
• a group consisting of an oxo group, a thioxo group, a C1-C3 chain hydrocarbon group, a C1-C3 alkoxy group {wherein said C1-C3 chain hydrocarbon group and said C1-C3 alkoxy group are optionally substituted with one or more halogen atom(s)}, a halogen atom, and a cyano group;
• Group C:
• a group consisting of a C1-C6 chain hydrocarbon group, a C1-C6 alkoxy group, a C1-C6 alkylthio group {wherein said C1-C6 chain hydrocarbon group, said C1-C6 alkoxy group, and said C1-C6 alkylthio group are optionally substituted with one or more substituent(s) selected from Group F}, a C3-C6 cycloalkyl group {wherein said C3-C6 cycloalkyl group is optionally substituted with one or more substituent(s) selected from Group B}, a cyano group, a nitro group, a halogen atom, and a hydroxy group;
• Group D:
• a group consisting of a C1-C6 chain hydrocarbon group, a C1-C6 alkoxy group, a C1-C6 alkylthio group, a C1-C6 alkylamino group, a C2-C8 dialkylamino group, a (C1-C6 alkyl)carbonyl group, a (C1-C6 alkoxy)carbonyl group, a (C1-C6 alkylamino)carbonyl group, a (C2-C8 dialkylamino)carbonyl group {wherein said C1-C6 chain hydrocarbon group, said C1-C6 alkoxy group, said C1-C6 alkylthio group, said C1-C6 alkylamino group, said C2-C8 dialkylamino group, said (C1-C6 alkyl)carbonyl group, said (C1-C6 alkoxy)carbonyl group, said (C1-C6 alkylamino)carbonyl group, and said (C2-C8 dialkylamino)carbonyl group are optionally substituted with one or more substituent(s) selected from Group F}, a C3-C10 alicyclic hydrocarbon group, a 3-10 membered nonaromatic heterocyclic group {wherein said C3-C10 alicyclic hydrocarbon group and said 3-10 membered nonaromatic heterocyclic group are optionally substituted with one or more substituent(s) selected from Group B}, a C6-C10 aryl group, a 5-10 membered aromatic heterocyclic group {wherein said C6-C10 aryl group and said 5-10 membered aromatic heterocyclic group are optionally substituted with one or more substituent(s) selected from Group C}, a halogen atom, a cyano group, a nitro group, a hydroxy group, and an amino group;
• Group F:
• a group consisting of a C3-C4 cycloalkyl group, a halogen atom, and a C1-C3 alkoxy group]
• or an N-oxide or an agriculturally acceptable salt thereof to a soybean or soil for cultivating a soybean.