Azole derivative, intermediate compound, method for producing azole derivative, agricultural or horticultural chemical agent, and protective agent for industrial material

A compound represented by Formula (I),

• or an N-oxide or agrochemically acceptable salt thereof, wherein:
• A is N;
• D is a hydrogen, a halogen group, or SRD;
• where RD is a hydrogen, a cyano group, a C1-C6-alkyl group, a C1-C6-haloalkyl group, a C2-C6-alkenyl group, a C2-C6-haloalkenyl group, a C2-C6-alkynyl group or a C2-C6-haloalkynyl group;
• R1 is a hydrogen, a C1-C6-alkyl group, a C2-C6-alkenyl group, a C2-C6-alkynyl group, a C3-C8-cycloalkyl group, a C3-C8-cycloalkyl-C1-C4-alkyl group, a phenyl group, a phenyl-C1-C4-alkyl group, a phenyl-C2-C4-alkenyl group, a phenyl-C2-C4-alkynyl group, or COXR5;
• where R5 is a hydrogen, a C1-C6-alkyl group, a C2-C6-alkenyl group, a C2-C6-alkynyl group, a C3-C8-cycloalkyl group, a C3-C8-cycloalkyl-C1-C4-alkyl group, a phenyl group, a phenyl-C1-C4-alkyl group, a phenyl-C2-C4-alkenyl group, or a phenyl-C2-C4-alkynyl group;
• X is a single bond, —O—, or —NR6—;
• R6 is a hydrogen, a C1-C6-alkyl group, a C2-C6-alkenyl group, a C2-C6-alkynyl group, a C3-C8-cycloalkyl group, a C3-C8-cycloalkyl-C1-C4-alkyl group, a phenyl group, a phenyl-C1-C4-alkyl group, a phenyl-C2-C4-alkenyl group, or a phenyl-C2-C4-alkynyl group;
• and R5 and R6 may form a ring;
• R2 is —OR7 or —NR8R9;
• R7, R8 and R9 are each independently a hydrogen, a C1-C6-alkyl group, a C2-C6-alkenyl group, a C2-C6-alkynyl group, a C3-C8-cycloalkyl group, a C3-C8-cycloalkyl-C1-C4-alkyl group, a phenyl group, a phenyl-C1-C4-alkyl group, a phenyl-C2-C4-alkenyl group, or a phenyl-C2-C4-alkynyl group, and R8 and R9 may form a ring,
• where aliphatic groups in R1, R2, R5, R6, R7, R8, and R9 may have 1, 2, 3 or the possible maximum number of the same or different groups Ra, and Ra is independently selected from a halogen group, a cyano group, a nitro group, a C1-C4-alkoxy group, and a C1-C4-haloalkoxy group;
• R4 is a halogen group, a cyano group, a nitro group, an amino group, a phenyl group, a phenyl-oxy group, a C1-C4-alkyl group, a C1-C4-haloalkyl group, a C1-C4-alkoxy group, a C1-C4-haloalkoxy group, a C1-C4-alkylamino group, a C1-C4-dialkylamino group, a C1-C4-alkylacylamino group, —SOR10, or —SF5;
• the cycloalkyl group or phenyl group parts in R1, R2, R5, R6, R7, R8, and R9, or the phenyl group part in R4 may have 1, 2, 3, 4, 5, or the possible maximum number of the same or different groups Rb, and Rb is independently selected from a halogen group, a cyano group, a nitro group, a C1-C4-alkyl group, a C1-C4-alkoxy group, a C1-C4-haloalkyl group, and a C1-C4-haloalkoxy group;
• R3 is a halogen group, a cyano group, a nitro group, a phenyl group, a phenyl-oxy group, a C1-C4-alkyl group, a C1-C4-haloalkyl group, a C1-C4-alkoxy group, a C1-C4-haloalkoxy group, —SOR10, or —SF5;
• where R10 is a C1-C4-alkyl group or a C1-C4-haloalkyl group;
• E is a phenyl group or a 6-membered heteroaromatic ring containing 1 or 2 N atoms;
• n R3 are bonded to any substitution sites;
• when E is a phenyl group, then n is 0, 1, 2, 3, or 4, and when E is a 6-membered heteroaromatic ring containing 1 or 2 N atoms, then n is 0, 1, or 2;
• Y is an oxygen atom, —CH2O—, —OCH2—, —NH—, —N(—C1-C4-alkyl)-, —N(—C3-C6-cycloalkyl)-, or —S(O)p—, which bonds to any sites of E;
• where p is 0, 1, or 2;
• Z is an aromatic hydrocarbon group which is a phenyl group or a naphthyl group, or a 5-membered or 6-membered heteroaromatic ring or 9-membered or 10-membered heteroaromatic ring formed of 2 rings, containing 1 to 4 heteroatoms selected from O, N, and S;
• and
• m R4 are bonded to any substitution sites;
• when Z is a phenyl group, then m is 1, 2, 3, 4, or 5 and when Z is a naphthyl group or a heteroaromatic ring, then m is 0, 1, 2, 3, or 4.