1. A fused ring substituted aromatic compound is shown in a general formula I:

wherein the content of the first and second substances,

q represents

Y represents halogen, haloalkyl, cyano, nitro or amino;

z represents hydrogen, halogen or hydroxy;

m represents CH or N;

Q₁、Q₂、Q₃、Q₄、Q₅、Q₆each independently represents O or S;

het represents a cyclic structure sharing two carbon atoms at 4-and 5-positions with the isoxazoline ring to form a fused ring, the cyclic structure being a 3-to 8-membered saturated or unsaturated carbocyclic ring or containing a group selected from O, S, N, NH, CO, SO₂Or C ═ N-O-R₁₄In which 1,2 or 3 hetero atoms in the saturated or unsaturated heterocyclic ring, except for the 4-and 5-positions, respectively, are replaced by X₂Or X₁Independently of the substitution, each other position on the Het is unsubstituted OR substituted by a group selected from halogen, cyano, nitro, alkyl, alkenyl, alkynyl, cycloalkyl, haloalkyl, haloalkenyl, haloalkynyl, halocycloalkyl, cycloalkyl substituted by alkyl, -OR₁₄、-SR₁₄、-SOR₁₄、-(CO)OR₁₄、-(SO₂)R₁₄、-N(R₁₄)₂OR-O- (CO) OR₁₄Is substituted with at least one radical group;

X₁、X₂each independently represents hydrogen, halogen, nitro, cyano, thiocyanato, hydroxyl, mercapto, sulfonic acid, formyl, haloformyl, azido, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl, cycloalkenylalkyl, -PO (OR')₂、-OR”、-(CO)R”、-SR”、-(SO)R”、-(SO₂)R”、-Si(R”)₃、-O(CO)R”、-O-(SO₂)R”、-S(CO)R”、-(SO₂)OR”、-O(CO)OR”、-(CO)(CO)OR”、-CR '═ N-OH, -CR' ═ N-O-R ", heterocyclylHeterocyclylalkyl, aryl, arylalkyl, amino, aminoalkyl, aminocarbonylalkyl, aminocarbonyloxyalkyl, aminothiocarbonyloxyalkyl, aminosulfonyl or aminosulfonyloxyalkyl, wherein,

said "alkyl", "alkenyl" OR "alkynyl" are each independently unsubstituted OR selected from halogen, cyano, hydroxy, mercapto, carboxyl, -OR ", (CO) R", -SR ", (SO)₂)R”、-O(CO)H、-O(CO)R”、-O-(SO₂) R ", - (CO) OR", -O (CO) OH, — O (CO) OR ", -O-alkyl- (CO) OH OR-O-alkyl- (CO) OR",

said "cycloalkyl", "cycloalkylalkyl", "cycloalkenyl", "cycloalkenylalkyl", "heterocyclyl", "heterocyclylalkyl", "aryl", OR "arylalkyl" are each independently unsubstituted OR substituted with a group selected from oxo, halogen, cyano, nitro, alkyl, alkenyl, alkynyl, cycloalkyl, haloalkyl, haloalkenyl, haloalkynyl, halocycloalkyl, cycloalkyl substituted with alkyl, -OR₁₄、-SR₁₄、-(CO)OR₁₄、-(SO₂)R₁₄、-N(R₁₄)₂OR-O-alkyl- (CO) OR₁₄Or two adjacent carbon atoms in the ring and-OCH which are unsubstituted or substituted by halogen₂CH₂-or-OCH₂O-forms a condensed ring,

said "amino", "aminoalkyl", "aminocarbonylalkyl", "aminocarbonyloxyalkyl", "aminothiocarbonyloxyalkyl", "aminosulfonyl" or "aminosulfonyloxyalkyl" groups are each independently unsubstituted or selected from-R₁₁、-OR₁₁、-(CO)R₁₁、-(CO)OR₁₁-alkyl- (CO) OR₁₁、-(SO₂)R₁₁、-(SO₂)OR₁₁-alkyl- (SO)₂)R₁₁、-(CO)N(R₁₂)₂Or- (SO)₂)N(R₁₂)₂Substituted with one or two groups;

r' independently represents hydrogen or halogenAn alkyl, alkoxy, alkoxyalkyl, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl, cycloalkenylalkyl, aryl, arylalkyl, heterocyclyl, OR heterocyclylalkyl group, wherein the "alkyl", "alkenyl", OR "alkynyl" groups are each independently unsubstituted OR substituted with halogen, and the "cycloalkyl", "cycloalkylalkyl", "cycloalkenyl", "cycloalkenylalkyl", "aryl", "arylalkyl", "heterocyclyl", OR "heterocyclylalkyl" groups are each independently unsubstituted OR substituted with a group selected from oxo, halogen, cyano, nitro, alkyl, alkenyl, alkynyl, cycloalkyl, haloalkyl, haloalkenyl, haloalkynyl, halocycloalkyl, cycloalkyl substituted with alkyl, -OR₁₄、-SR₁₄、-(CO)OR₁₄、-(SO₂)R₁₄、-N(R₁₄)₂OR-O-alkyl- (CO) OR₁₄Or two adjacent carbon atoms in the ring and-OCH which are unsubstituted or substituted by halogen₂CH₂-or-OCH₂O-forms a fused ring;

r "each independently represents an alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl, cycloalkenylalkyl, aryl, arylalkyl, arylalkenyl, heterocyclyl, heterocyclylalkyl, OR heterocyclylalkenyl group, wherein the" alkyl "," alkenyl ", OR" alkynyl "each independently is unsubstituted OR selected from halogen, cyano, trialkylsilyl, -OR₁₃、-SR₁₃、-O(CO)R₁₃、-(CO)R₁₃、-(CO)OR₁₃OR-O (CO) OR₁₃Each of said "cycloalkyl", "cycloalkylalkyl", "cycloalkenyl", "cycloalkenylalkyl", "aryl", "arylalkyl", "arylalkenyl", "heterocyclyl", "heterocyclylalkyl", OR "heterocyclylalkenyl" is independently unsubstituted OR substituted with at least one group selected from oxo, halogen, cyano, nitro, alkyl, alkenyl, alkynyl, cycloalkyl, haloalkyl, haloalkenyl, haloalkynyl, halocycloalkyl, cycloalkyl substituted with alkyl, -OR₁₄、-SR₁₄、-(CO)OR₁₄、-(SO₂)R₁₄、-N(R₁₄)₂OR-O-alkyl- (CO) OR₁₄Or two adjacent carbon atoms in the ring and-OCH which are unsubstituted or substituted by halogen₂CH₂-or-OCH₂O-forms a fused ring;

W₁represents O, S, NH or N-alkyl;

W₂represents OW₃、SW₃Or N (W)₃)₂；

W₃Each independently represents hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, heterocyclyl, aryl, heterocyclyl, or heterocyclyl, Wherein each of said "alkyl", "alkenyl" or "alkynyl" is independently unsubstituted or selected from halogen, cyano, nitro, cycloalkyl, trialkylsilyl, cycloalkenyl, heterocyclyl, aryl, heteroaryl, and mixtures thereof, Each of said "cycloalkyl", "cycloalkenyl", "heterocyclyl" OR "aryl" is independently unsubstituted OR substituted with at least one group selected from oxo, halogen, cyano, nitro, alkyl, alkenyl, alkynyl, cycloalkyl, haloalkyl, haloalkenyl, haloalkynyl, halocycloalkyl, cycloalkyl substituted with alkyl, -OR₁₄、-SR₁₄、-(CO)OR₁₄、-(SO₂)R₁₄、-N(R₁₄)₂OR-O-alkyl- (CO) OR₁₄Is substituted by at least one group in (a), or two adjacent ringsHaving carbon atoms and-OCH being unsubstituted or substituted by halogen₂CH₂-or-OCH₂O-forms a fused ring;

or N (W)₃)₂Represents an unsubstituted or substituted heterocyclic group having a nitrogen atom at the 1-position;

X₁₁each independently represents hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl, cycloalkenylalkyl, heterocyclyl, heterocyclylalkyl, aryl, OR arylalkyl, wherein the "cycloalkyl", "cycloalkylalkyl", "cycloalkenyl", "cycloalkenylalkyl", "heterocyclyl", "heterocyclylalkyl", "aryl", OR "arylalkyl" each independently is unsubstituted OR selected from oxo, halogen, cyano, nitro, alkyl, alkenyl, alkynyl, cycloalkyl, haloalkyl, haloalkenyl, haloalkynyl, halocycloalkyl, cycloalkyl substituted with alkyl, -OR₁₄、-SR₁₄、-(CO)OR₁₄、-(SO₂)R₁₄、-N(R₁₄)₂OR-O-alkyl- (CO) OR₁₄Or two adjacent carbon atoms in the ring and-OCH which are unsubstituted or substituted by halogen₂CH₂-or-OCH₂O-forms a fused ring;

X₁₂each independently represents an alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl, cycloalkenylalkyl, heterocyclyl, heterocyclylalkyl, aryl, OR arylalkyl group, wherein the "cycloalkyl", "cycloalkylalkyl", "cycloalkenyl", "cycloalkenylalkyl", "heterocyclyl", "heterocyclylalkyl", "aryl", OR "arylalkyl" groups are each independently unsubstituted OR selected from oxo, halogen, cyano, nitro, alkyl, alkenyl, alkynyl, cycloalkyl, haloalkyl, haloalkenyl, haloalkynyl, halocycloalkyl, cycloalkyl substituted with alkyl, -OR₁₄、-SR₁₄、-(CO)OR₁₄、-(SO₂)R₁₄、-N(R₁₄)₂OR-O-alkyl- (CO) OR₁₄Or two adjacent carbon atoms in the ring and-OCH which are unsubstituted or substituted by halogen₂CH₂-or-OCH₂O-forms a fused ring;

X₁₃、X₁₄each independently represents hydrogen, halogen, cyano, alkoxy, alkoxyalkyl, alkylcarbonyl, alkoxycarbonyl, alkylsulfonyl, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl, cycloalkenylalkyl, aryl, arylalkyl, heterocyclyl or heterocyclylalkyl, or the group CX₁₃X₁₄Together forming an unsubstituted or substituted cyclic structure, or a group NX₁₃X₁₄Together form an unsubstituted OR substituted heterocyclyl group having a nitrogen atom at the 1-position, wherein "alkyl", "alkenyl" OR "alkynyl" are each independently unsubstituted OR substituted with halogen and "cycloalkyl", "cycloalkylalkyl", "cycloalkenyl", "cycloalkenylalkyl", "aryl", "arylalkyl", "heterocyclyl" OR "heterocyclylalkyl" are each independently unsubstituted OR substituted with a group selected from oxo, halogen, cyano, nitro, alkyl, alkenyl, alkynyl, cycloalkyl, haloalkyl, haloalkenyl, haloalkynyl, halocycloalkyl, cycloalkyl substituted with alkyl, -OR₁₄、-SR₁₄、-(CO)OR₁₄、-(SO₂)R₁₄、-N(R₁₄)₂OR-O-alkyl- (CO) OR₁₄Or two adjacent carbon atoms in the ring and-OCH which are unsubstituted or substituted by halogen₂CH₂-or-OCH₂O-forms a fused ring;

R₁、R₂、R₆、R₁₀、R₁₇、R₁₈、R₂₂、R₂₅、R₃₂each independently represents hydrogen, cyano, alkyl, alkenyl, alkynyl, formylalkyl, cyanoalkyl, amino, aminoalkyl, aminocarbonyl, aminocarbonylalkyl, aminosulfonyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl, cycloalkenylalkyl, heterocyclyl, heterocyclylalkyl, aryl, arylalkyl, R₄R₅N-(CO)-NR₃-、R₃-S(O)_m- (alkyl)_n-、R₃-O- (alkyl)_n-、R₃- (CO) - (alkyl)_n-、R₃-O- (alkyl)_n-(CO)-、R₃- (CO) -O- (alkyl)_n-、R₃-S- (CO) - (alkyl)_n-、R₃-O- (CO) -alkyl-or R₃-O- (CO) -O-alkyl-, wherein,

each of said "alkyl", "alkenyl" or "alkynyl" is independently unsubstituted or substituted with halogen,

said "amino", "aminoalkyl", "aminocarbonyl", "aminocarbonylalkyl" or "aminosulfonyl" are each independently unsubstituted or selected from-R₁₁、-OR₁₁、-(CO)R₁₁、-(CO)OR₁₁-alkyl- (CO) OR₁₁、-(SO₂)R₁₁、-(SO₂)OR₁₁-alkyl- (SO)₂)R₁₁、-(CO)N(R₁₂)₂Or- (SO)₂)N(R₁₂)₂Substituted with one or two of the groups in (a),

said "cycloalkyl", "cycloalkylalkyl", "cycloalkenyl", "cycloalkenylalkyl", "heterocyclyl", "heterocyclylalkyl", "aryl", OR "arylalkyl" are each independently unsubstituted OR substituted with a group selected from oxo, halogen, cyano, nitro, alkyl, alkenyl, alkynyl, cycloalkyl, haloalkyl, haloalkenyl, haloalkynyl, halocycloalkyl, cycloalkyl substituted with alkyl, -OR₁₄、-SR₁₄、-(CO)OR₁₄、-(SO₂)R₁₄、-N(R₁₄)₂OR-O-alkyl- (CO) OR₁₄Or two adjacent carbon atoms in the ring and-OCH which are unsubstituted or substituted by halogen₂CH₂-or-OCH₂O-forms a fused ring;

or R₁₇、R₁₈Together form-CH which is unsubstituted or substituted by at least one group selected from halogen, alkyl or haloalkyl₂CH₂CH₂CH₂-or-CH₂CH₂OCH₂-；

R₃、R₄、R₅Each independently represents hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl, cycloalkenylalkyl, heterocyclyl, heterocyclylalkyl, aryl, OR arylalkyl, wherein the "alkyl", "alkenyl", OR "alkynyl" each independently is unsubstituted OR substituted with halogen, and the "cycloalkyl", "cycloalkylalkyl", "cycloalkenyl", "cycloalkenylalkyl", "heterocyclyl", "heterocyclylalkyl", "aryl", OR "arylalkyl" each independently is unsubstituted OR substituted with a group selected from oxo, halogen, cyano, nitro, alkyl, alkenyl, alkynyl, cycloalkyl, haloalkyl, haloalkenyl, haloalkynyl, halocycloalkyl, cycloalkyl substituted with alkyl, -OR₁₄、-SR₁₄、-(CO)OR₁₄、-(SO₂)R₁₄、-N(R₁₄)₂OR-O-alkyl- (CO) OR₁₄Or two adjacent carbon atoms in the ring and-OCH which are unsubstituted or substituted by halogen₂CH₂-or-OCH₂O-forms a fused ring;

R₇、R₈、R₇’、R₈’、R₉、R₁₉、R₂₀、R₂₁、R₂₃、R₂₄、R₂₆、R₂₇、R₂₈、R₂₉、R₃₀、R₃₁、R₃₃、R₃₄、R₃₅、R₃₆、R₃₇、R₃₈、R₃₉、R₄₀、R₄₁、R₄₂、R₄₃、R₄₄、R₄₅、R₄₆、R₄₇、R₄₈、R₄₉、R₅₀、R₅₁each independently represents hydrogen, halogen, hydroxy, mercapto, formyl, hydroxyalkyl, nitro, cyano, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl, cycloalkenylalkyl, -OR₁₁、-SR₁₁、-(SO)R₁₁、-(SO₂)R₁₁、-(SO₂)OR₁₁、-O(SO₂)R₁₁、-N(R₁₂)₂Phenyl or benzyl, wherein,

said "alkyl", "alkenyl", "alkynyl", "cycloalkyl", "cycloalkylalkyl", "cycloalkenyl" or "cycloalkenylalkyl" each independently being unsubstituted or substituted with halogen, said "phenyl" or "benzyl" each independently being unsubstituted or substituted with at least one group selected from halogen, cyano, nitro, alkyl, haloalkyl, alkoxycarbonyl, alkylthio, alkylsulfonyl, alkoxy or haloalkoxy;

or R₇、R₈Together form-CH which is unsubstituted or substituted by at least one group selected from halogen, alkyl or haloalkyl₂CH₂CH₂CH₂-or-CH ═ CH-;

or R₁₉、R₂₀Together form-CH which is unsubstituted or substituted by at least one group selected from halogen, alkyl or haloalkyl₂CH₂CH₂CH₂-or-CH₂CH＝CHCH₂-；

Or R₂₁、R₂₂Together form-CH which is unsubstituted or substituted by at least one group selected from halogen, alkyl or haloalkyl₂CH₂CH₂-、-CH₂OCH₂CH₂-or-CH₂CH₂CH₂CH₂-；

R₁₁Each independently represents an alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl, cycloalkenylalkyl, phenyl, or benzyl group, wherein the "alkyl", "alkenyl", or "alkynyl" groups are each independently unsubstituted or substituted with halogen, and the "phenyl" or "benzyl" groups are each independently unsubstituted or substituted with at least one group selected from halogen, cyano, nitro, alkyl, haloalkyl, alkoxycarbonyl, alkylthio, alkylsulfonyl, alkoxy, or haloalkoxy;

R₁₂each independently represents hydrogen, alkyl, alkenyl, alkynyl, alkoxy, alkylsulfonylCycloalkyl, cycloalkylalkyl, cycloalkenyl or cycloalkenylalkyl, or- (CO) N (R)₁₂)₂Or- (SO)₂)N(R₁₂)₂Group N (R) of (1)₁₂)₂Each independently represents an unsubstituted or substituted heterocyclic group having a nitrogen atom at the 1-position;

R₁₃each independently represents an alkyl, alkenyl, alkynyl, cycloalkyl, phenyl or phenyl substituted by at least one group selected from: halogen, cyano, nitro, alkyl, haloalkyl, alkoxy, haloalkoxy, alkoxycarbonyl, alkylthio, alkylsulfonyl or phenoxy substituted by at least one group selected from halogen, cyano, nitro, alkyl, haloalkyl, alkoxy or haloalkoxy;

R₁₄each independently represents hydrogen, alkyl, haloalkyl, phenyl or phenyl substituted by at least one group selected from halogen, cyano, nitro, alkyl, haloalkyl, alkoxycarbonyl, alkylthio, alkylsulfonyl, alkoxy or haloalkoxy;

R₁₅、R₁₆、R₅₂each independently represents hydrogen, halogen, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl, or cycloalkenylalkyl, wherein the "alkyl", "alkenyl", "alkynyl", "cycloalkyl", "cycloalkylalkyl", "cycloalkenyl", or "cycloalkenylalkyl" each independently is unsubstituted or substituted with halogen;

m represents 0,1 or 2; n independently represents 0 or 1.

2. A fused ring substituted aromatic compound according to claim 1,

y represents halogen, halogeno-C1-C8 alkyl, cyano, nitro or amino;

het represents a cyclic structure sharing two carbon atoms at 4-and 5-positions with the isoxazoline ring to form a fused ring, the cyclic structure being a 3-to 8-membered saturated or unsaturated carbocyclic ring or containing a group selected from O, S, N, NH, CO, SO₂Or C ═ N-O-R₁₄With 1,2 or 3 hetero atoms in the hetero ring being saturated or unsaturatedRing, except for the 4-and 5-positions by X respectively₂Or X₁Independently of the substitution, the other positions on the Het are each unsubstituted OR substituted by a group selected from halogen, cyano, nitro, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, haloC 1-C8 alkyl, haloC 2-C8 alkenyl, haloC 2-C8 alkynyl, haloC 3-C8 cycloalkyl, C3-C8 cycloalkyl substituted by C1-C8 alkyl, -OR₁₄、-SR₁₄、-SOR₁₄、-(CO)OR₁₄、-(SO₂)R₁₄、-N(R₁₄)₂OR-O- (CO) OR₁₄Is substituted with at least one radical group;

X₁、X₂each independently represents hydrogen, halogen, nitro, cyano, thiocyanato, hydroxyl, mercapto, sulfonic acid, formyl, haloformyl, azido, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkyl C1-C8 alkyl, C3-C8 cycloalkenyl, C3-C8 cycloalkenyl C1-C8 alkyl, -PO (OR')₂、-OR”、-(CO)R”、-SR”、-(SO)R”、-(SO₂)R”、-Si(R”)₃、-O(CO)R”、-O-(SO₂)R”、-S(CO)R”、-(SO₂)OR”、-O(CO)OR”、-(CO)(CO)OR”、-CR '═ N-OH, -CR' ═ N-O-R ", heterocyclyl C1-C8 alkyl, aryl C1-C8 alkyl, amino C1-C8 alkyl, aminocarbonyl C1-C8 alkyl, aminocarbonyloxy C1-C8 alkyl, aminothiocarbonyloxy C1-C8 alkyl, aminosulfonyl or aminosulfonyloxy C1-C8 alkyl, where,

said "C1-C8 alkyl", "C2-C8 alkenyl" OR "C2-C8 alkynyl" are each independently unsubstituted OR substituted with a substituent selected from the group consisting of halogen, cyano, hydroxy, mercapto, carboxyl, -OR ", (CO) R", (SR) ", - (SO)₂)R”、-O(CO)H、-O(CO)R”、-O-(SO₂) R ", - (CO) OR", -O (CO) OH, — O (CO) OR ", -O- (C1-C8 alkyl) - (CO) OH OR-O- (C1-C8 alkyl) - (CO) OR",

the "C3-C8 cycloalkyl"),"C3-C8 cycloalkyl C1-C8 alkyl", "C3-C8 cycloalkenyl", "C3-C8 cycloalkenyl C1-C8 alkyl", "heterocyclyl C1-C8 alkyl", "aryl" OR "aryl C1-C8 alkyl" are each independently unsubstituted OR substituted by groups selected from oxo, halogen, cyano, nitro, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, halo C1-C8 alkyl, halo C2-C8 alkenyl, halo C2-C8 alkynyl, halo C3-C8 cycloalkyl, C3-C8 cycloalkyl substituted by C1-C8 alkyl, -OR₁₄、-SR₁₄、-(CO)OR₁₄、-(SO₂)R₁₄、-N(R₁₄)₂OR-O- (C1-C8 alkyl) - (CO) OR₁₄Or two adjacent carbon atoms in the ring and-OCH which are unsubstituted or substituted by halogen₂CH₂-or-OCH₂O-forms a condensed ring,

the "amino", "amino C1-C8 alkyl", "aminocarbonyl C1-C8 alkyl", "aminocarbonyloxy C1-C8 alkyl", "aminothiocarbonyloxy C1-C8 alkyl", "aminosulfonyl" or "aminosulfonyloxy C1-C8 alkyl" are each independently unsubstituted or selected from the group consisting of₁₁、-OR₁₁、-(CO)R₁₁、-(CO)OR₁₁- (C1-C8 alkyl) - (CO) OR₁₁、-(SO₂)R₁₁、-(SO₂)OR₁₁- (C1-C8 alkyl) - (SO)₂)R₁₁、-(CO)N(R₁₂)₂Or- (SO)₂)N(R₁₂)₂Substituted with one or two groups;

r' independently represents hydrogen, halogen, C1-C8 alkoxy, C1-C8 alkoxy C1-C8 alkyl, C1-C8 alkyl, C8-C8 alkenyl, C8-C8 alkynyl, C8-C8 cycloalkyl C8 alkyl, C8-C8 cycloalkenyl C8 alkyl, aryl C8-C8 alkyl, heterocyclyl or heterocyclyl C8-C8 alkyl, wherein "C8-C8 alkyl", "C8-C8 alkenyl" or "C8-C8 alkynyl" independently represents unsubstituted or substituted by halogen, and "C8-C8 cycloalkyl", "C8-C8 alkyl", "C8-C8 cycloalkenyl" or "C8-C8 cycloalkenyl" aryl 8 "8 alkyl, "aryl C1-C8 alkyl" or "heterocycleThe group "OR" heterocyclyl C1-C8 alkyl "is each independently unsubstituted OR substituted by a group selected from oxo, halogen, cyano, nitro, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, haloC 1-C8 alkyl, haloC 2-C8 alkenyl, haloC 2-C8 alkynyl, haloC 3-C8 cycloalkyl, C3-C8 cycloalkyl substituted with C1-C8 alkyl, -OR₁₄、-SR₁₄、-(CO)OR₁₄、-(SO₂)R₁₄、-N(R₁₄)₂OR-O- (C1-C8 alkyl) - (CO) OR₁₄Or two adjacent carbon atoms in the ring and-OCH which are unsubstituted or substituted by halogen₂CH₂-or-OCH₂O-forms a fused ring;

r' each independently represents C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkyl C1-C8 alkyl, C3-C8 cycloalkenyl, C3-C8 cycloalkenyl C1-C8 alkyl, aryl C1-C8 alkyl, aryl C2-C8 alkenyl, heterocyclyl C1-C8 alkyl, OR heterocyclyl C2-C8 alkenyl, wherein each of said "C1-C8 alkyl", "C2-C8 alkenyl", OR "C2-C8 alkynyl" is independently unsubstituted OR selected from halogen, cyano, tri C1-C8 alkylsilyl, -OR₁₃、-SR₁₃、-O(CO)R₁₃、-(CO)R₁₃、-(CO)OR₁₃OR-O (CO) OR₁₃(iii) said "C3-C8 cycloalkyl", "C3-C8 cycloalkyl C1-C8 alkyl", "C3-C8 cycloalkenyl", "C3-C8 cycloalkenyl C1-C8 alkyl", "aryl C1-C8 alkyl", "aryl C2-C8 alkenyl", "heterocyclyl C1-C8 alkyl" or "heterocyclyl C2-C8 alkenyl", each independently being unsubstituted or selected from oxo, halogen, cyano, nitro, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, halogenated C1-C8 alkyl, halogenated C2-C8 alkenyl, halogenated C2-C8 alkynyl, halogenated C3-C8 cycloalkyl, C3-C8 cycloalkyl substituted by C1-C8 alkyl, -OR.₁₄、-SR₁₄、-(CO)OR₁₄、-(SO₂)R₁₄、-N(R₁₄)₂OR-O- (C1-C8 alkyl) - (CO) OR₁₄Or two adjacent carbon atoms in the ring with unsubstituted or halogensubstituted-OCH₂CH₂-or-OCH₂O-forms a fused ring;

W₁represents O, S, NH or N- (C1-C8 alkyl);

W₃each independently represents hydrogen, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkenyl, heterocyclyl, aryl, heteroaryl, substituted heteroaryl, or substituted heteroaryl, Wherein each of said "C1-C8 alkyl", "C2-C8 alkenyl" or "C2-C8 alkynyl" is independently unsubstituted or selected from the group consisting of halogen, cyano, nitro, C3-C8 cycloalkyl, tri-C1-C8 alkylsilyl, C3-C8 cycloalkenyl, heterocyclyl, aryl, heteroaryl, and heteroaryl, (ii) said "C3-C8 cycloalkyl", "C3-C8 cycloalkenyl", "heterocyclyl" OR "aryl" are each independently unsubstituted OR substituted with a group selected from oxo, halogen, cyano, nitro, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, halogenated C1-C8 alkyl, halogenated C2-C8 alkenyl, halogenated C2-C8 alkynyl, halogenated C3-C8 cycloalkyl, C3-C8 cycloalkyl substituted with C1-C8 alkyl, -OR₁₄、-SR₁₄、-(CO)OR₁₄、-(SO₂)R₁₄、-N(R₁₄)₂OR-O- (C1-C8 alkyl) - (CO) OR₁₄Or two adjacent carbon atoms in the ring and-OCH which are unsubstituted or substituted by halogen₂CH₂-or-OCH₂O-forms a fused ring;

or N (W)₃)₂RepresentsWhich is unsubstituted or substituted by at least one group selected from oxo, C1-C8 alkyl or C1-C8 alkoxycarbonyl;

X₁₁each independently represents hydrogen, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkyl C1-C8 alkyl, C8-C8 cycloalkenyl, heterocyclyl C8-C8 alkyl, aryl, or aryl C8-C8 alkyl, wherein said "C8-C8 cycloalkyl", "C8-C8 cycloalkyl C8-C8 alkyl", "C8-C8 cycloalkenyl C8-C8 alkyl", "heterocyclyl C8-C8 alkyl", "aryl", or "aryl C8-C8 alkyl" are each independently unsubstituted or selected from oxo, halogen, cyano, nitro, C8-C8 alkyl, C8-C8 alkenyl, C8-C8 alkynyl, C3-C8 cycloalkyl, halo-C1-C8 alkyl, halo-C2-C8 alkenyl, halo-C2-C8 alkynyl, halo-C3-C8 cycloalkyl, C3-C8 cycloalkyl substituted by C1-C8 alkyl, -OR₁₄、-SR₁₄、-(CO)OR₁₄、-(SO₂)R₁₄、-N(R₁₄)₂OR-O- (C1-C8 alkyl) - (CO) OR₁₄Or two adjacent carbon atoms in the ring and-OCH which are unsubstituted or substituted by halogen₂CH₂-or-OCH₂O-forms a fused ring;

X₁₂each independently represents C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkyl C1-C8 alkyl, C8-C8 cycloalkenyl, heterocyclyl C8-C8 alkyl, aryl, or aryl C8-C8 alkyl, wherein said "C8-C8 cycloalkyl", "C8-C8 cycloalkyl C8-C8 alkyl", "C8-C8 cycloalkenyl C8-C8 alkyl", "heterocyclyl" C8-C8 alkyl "," aryl ", or" aryl C8-C8 alkyl "are each independently unsubstituted or selected from oxo, halogen, cyano, nitro, C8-C8 alkyl, C8-C8 alkenyl, C8-C8 alkynyl, C8-C8 alkynyl, C3-C8 cycloalkyl, halo-C1-C8 alkyl, halo-C2-C8 alkenyl, halo-C2-C8 alkynyl, halo-C3-C8 cycloalkyl, C3-C8 cycloalkyl substituted by C1-C8 alkyl, -OR₁₄、-SR₁₄、-(CO)OR₁₄、-(SO₂)R₁₄、-N(R₁₄)₂OR-O- (C1-C8 alkyl) - (CO) OR₁₄Or two adjacent carbon atoms in the ring and-OCH which are unsubstituted or substituted by halogen₂CH₂-or-OCH₂O-forms a fused ring;

X₁₃、X₁₄each independently represents hydrogen, halogen, cyano, C1-C8 alkoxy, C1-C8 alkoxy C1-C8 alkyl, C1-C8 alkylcarbonyl, C1-C8 alkoxycarbonyl, C1-C8 alkylsulfonyl, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkyl C1-C8 alkyl, C3-C8 cycloalkenyl, C3-C8 cycloalkenyl C1-C8 alkyl, aryl C1-C8 alkyl, heterocyclyl or heterocyclyl C1-C8 alkyl, or the group CX₁₃X₁₄Together form a 5-to 8-membered carbocyclic or oxygen, sulfur or nitrogen containing heterocyclic ring, or a group NX₁₃X₁₄Are formed togetherWherein each of said "C1-C8 alkyl", "C2-C8 alkenyl" or "C2-C8 alkynyl" is independently unsubstituted or substituted by halogen, and said "C3-C8 cycloalkyl", "C3-C8 cycloalkyl C1-C8 alkyl", "C3-C8 cycloalkenyl", "C3-C8 cycloalkenyl C8-C8 alkyl", "aryl C8-C8 alkyl", "heterocyclyl" or "heterocyclyl C8-C8 alkyl" is independently unsubstituted or substituted by an alkyl group selected from oxo, halogen, cyano, nitro, C8-C8 alkyl, C8-C8 alkenyl, C8-C8 alkynyl, C8-C8 cycloalkyl, haloC 8-C8 alkyl, haloC 8-C8 alkenyl, haloC 8-C8 alkynyl, haloC 8-C8 alkenyl, haloC 8-C8 cycloalkyl, C8-C8 cycloalkyl 8-C8 alkyl, C8 cycloalkyl 8-C8 alkyl, -OR₁₄、-SR₁₄、-(CO)OR₁₄、-(SO₂)R₁₄、-N(R₁₄)₂OR-O- (C1-C8 alkyl) - (CO) OR₁₄Or two adjacent carbon atoms in the ring and-OCH which are unsubstituted or substituted by halogen₂CH₂-or-OCH₂O-forms a fused ring, the "5-to 8-membered carbocyclic ring or heterocyclic ring containing oxygen, sulfur or nitrogen" is unsubstituted or is selected from at least one of C1-C8 alkyl, C1-C8 alkoxycarbonyl or benzylOne group is substituted or forms a fused ring structure with an aryl or heterocyclic group; the above-mentionedIs unsubstituted or substituted by at least one group selected from oxo, C1-C8 alkyl or C1-C8 alkoxycarbonyl;

R₁、R₂、R₆、R₁₀、R₁₇、R₁₈、R₂₂、R₂₅、R₃₂each independently represents hydrogen, cyano, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, formyl C1-C8 alkyl, cyano C1-C8 alkyl, amino C1-C8 alkyl, aminocarbonyl C1-C8 alkyl, aminosulfonyl, C3-C8 cycloalkyl, C3-C8 cycloalkyl C1-C8 alkyl, C3-C8 cycloalkenyl, C3-C8 cycloalkenyl C1-C8 alkyl, heterocyclyl C1-C8 alkyl, aryl C1-C8 alkyl, R8 alkyl₄R₅N-(CO)-NR₃-、R₃-S(O)_m- (C1-C8 alkyl)_n-、R₃-O- (C1-C8 alkyl)_n-、R₃- (CO) - (C1-C8 alkyl)_n-、R₃-O- (C1-C8 alkyl)_n-(CO)-、R₃- (CO) -O- (C1-C8 alkyl)_n-、R₃-S- (CO) - (C1-C8 alkyl)_n-、R₃-O- (CO) - (C1-C8 alkyl) -or R₃-O- (CO) -O- (C1-C8 alkyl) -, wherein,

the "C1-C8 alkyl", "C2-C8 alkenyl" or "C2-C8 alkynyl" each independently is unsubstituted or substituted with halogen,

the "amino", "amino C1-C8 alkyl", "aminocarbonyl C1-C8 alkyl" or "aminosulfonyl" groups are each independently unsubstituted or selected from the group consisting of₁₁、-OR₁₁、-(CO)R₁₁、-(CO)OR₁₁- (C1-C8 alkyl) - (CO) OR₁₁、-(SO₂)R₁₁、-(SO₂)OR₁₁- (C1-C8 alkyl) - (SO)₂)R₁₁、-(CO)N(R₁₂)₂Or- (SO)₂)N(R₁₂)₂Substituted with one or two of the groups in (a),

the "C3-C8 cycloalkyl", "C3-C8 cycloalkyl C1-C8 alkyl", "C3-C8 cycloalkenyl", "C3-C8 cycloalkenyl C1-C8 alkyl", "heterocyclyl C1-C8 alkyl", "aryl" OR "aryl C1-C8 alkyl" are each independently unsubstituted OR selected from oxo, halogen, cyano, nitro, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, halo C1-C8 alkyl, halo C2-C8 alkenyl, halo C8-C8 alkynyl, halo C8-C8 cycloalkyl, C8-C8 cycloalkyl substituted by C8-C8 alkyl, -OR₁₄、-SR₁₄、-(CO)OR₁₄、-(SO₂)R₁₄、-N(R₁₄)₂OR-O- (C1-C8 alkyl) - (CO) OR₁₄Or two adjacent carbon atoms in the ring and-OCH which are unsubstituted or substituted by halogen₂CH₂-or-OCH₂O-forms a fused ring;

or R₁₇、R₁₈Together form-CH which is unsubstituted or substituted by at least one group selected from halogen, C1-C8 alkyl or haloC 1-C8 alkyl₂CH₂CH₂CH₂-or-CH₂CH₂OCH₂-；

R₃、R₄、R₅Each independently represents hydrogen, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkyl C1-C8 alkyl, C8-C8 cycloalkenyl, heterocyclyl C8-C8 alkyl, aryl or aryl C8-C8 alkyl, wherein said "C8-C8 alkyl", "C8-C8 alkenyl" or "C8-C8 alkynyl" are each independently unsubstituted or substituted by halogen and said "C8-C8 cycloalkyl", "C8-C8 cycloalkyl C8-C8 alkyl", "C8-C8 cycloalkenyl", "C8-C8 alkyl", "C8-C8 aryl" or "aryl is each independently unsubstituted or substituted by a halogen, Halogen, cyano, nitro, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, halogenated C1-C8 alkyl, halogenated alkylC2-C8 alkenyl, halogenated C2-C8 alkynyl, halogenated C3-C8 cycloalkyl, C3-C8 cycloalkyl substituted by C1-C8 alkyl, -OR₁₄、-SR₁₄、-(CO)OR₁₄、-(SO₂)R₁₄、-N(R₁₄)₂OR-O- (C1-C8 alkyl) - (CO) OR₁₄Or two adjacent carbon atoms in the ring and-OCH which are unsubstituted or substituted by halogen₂CH₂-or-OCH₂O-forms a fused ring;

R₇、R₈、R₇’、R₈’、R₉、R₁₉、R₂₀、R₂₁、R₂₃、R₂₄、R₂₆、R₂₇、R₂₈、R₂₉、R₃₀、R₃₁、R₃₃、R₃₄、R₃₅、R₃₆、R₃₇、R₃₈、R₃₉、R₄₀、R₄₁、R₄₂、R₄₃、R₄₄、R₄₅、R₄₆、R₄₇、R₄₈、R₄₉、R₅₀、R₅₁each independently represents hydrogen, halogen, hydroxyl, sulfhydryl, formyl, hydroxyl C1-C8 alkyl, nitro, cyano, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkyl C1-C8 alkyl, C3-C8 cycloalkenyl, C3-C8 cycloalkenyl C1-C8 alkyl, -OR₁₁、-SR₁₁、-(SO)R₁₁、-(SO₂)R₁₁、-(SO₂)OR₁₁、-O(SO₂)R₁₁、-N(R₁₂)₂Phenyl or benzyl, wherein,

said "C1-C8 alkyl", "C2-C8 alkenyl", "C2-C8 alkynyl", "C3-C8 cycloalkyl", "C3-C8 cycloalkyl C1-C8 alkyl", "C3-C8 cycloalkenyl" or "C3-C8 cycloalkenyl C1-C8 alkyl" each independently being unsubstituted or substituted by halogen, said "phenyl" or "benzyl" each independently being unsubstituted or substituted by at least one group selected from halogen, cyano, nitro, C1-C8 alkyl, halo C1-C8 alkyl, C1-C8 alkoxycarbonyl 1-C8 alkylthio, C1-C8 alkylsulfonyl, C1-C8 alkoxy or halo C1-C8 alkoxy;

or R₇、R₈Together form-CH which is unsubstituted or substituted by at least one group selected from halogen, C1-C8 alkyl or haloC 1-C8 alkyl₂CH₂CH₂CH₂-or-CH ═ CH-;

or R₁₉、R₂₀Together form-CH which is unsubstituted or substituted by at least one group selected from halogen, C1-C8 alkyl or haloC 1-C8 alkyl₂CH₂CH₂CH₂-or-CH₂CH＝CHCH₂-；

Or R₂₁、R₂₂Together form-CH which is unsubstituted or substituted by at least one group selected from halogen, C1-C8 alkyl or haloC 1-C8 alkyl₂CH₂CH₂-、-CH₂OCH₂CH₂-or-CH₂CH₂CH₂CH₂-；

R₁₁Each independently represents C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkyl C1-C8 alkyl, C3-C8 cycloalkenyl, C3-C8 cycloalkenyl C1-C8 alkyl, phenyl or benzyl, wherein said "C1-C8 alkyl", "C2-C8 alkenyl" or "C2-C8 alkynyl" are each independently unsubstituted or substituted with halogen, said "phenyl" or "benzyl" are each independently unsubstituted or substituted with at least one group selected from halogen, cyano, nitro, C8-C8 alkyl, haloC 8-C8 alkyl, C8-C8 alkoxycarbonyl, C8-C8 alkylthio, C8-C8 alkylsulfonyl, C8-C8 alkoxy or haloC 8-C8 alkoxy;

R₁₂each independently represents hydrogen, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C1-C8 alkoxy, C1-C8 alkylsulfonyl, C3-C8 cycloalkyl, C3-C8 cycloalkyl C1-C8 alkyl, C3-C8 cycloalkenyl or C3-C8 cycloalkenyl C1-C8 alkyl, or- (CO) N (R) N₁₂)₂Or- (SO)₂)N(R₁₂)₂Group N (R) of (1)₁₂)₂Each independently represents Which is unsubstituted or substituted by at least one group selected from oxo, C1-C8 alkyl or C1-C8 alkoxycarbonyl;

R₁₃each independently represents C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, phenyl, or phenyl substituted by at least one group selected from: halogen, cyano, nitro, C1-C8 alkyl, halogenated C1-C8 alkyl, C1-C8 alkoxy, halogenated C1-C8 alkoxy, C1-C8 alkoxycarbonyl, C1-C8 alkylthio, C1-C8 alkylsulfonyl or phenoxy substituted by at least one group selected from halogen, cyano, nitro, C1-C8 alkyl, halogenated C1-C8 alkyl, C1-C8 alkoxy or halogenated C1-C8 alkoxy;

R₁₄each independently represents hydrogen, C1-C8 alkyl, halogenated C1-C8 alkyl, phenyl or phenyl substituted by at least one group selected from halogen, cyano, nitro, C1-C8 alkyl, halogenated C1-C8 alkyl, C1-C8 alkoxycarbonyl, C1-C8 alkylthio, C1-C8 alkylsulfonyl, C1-C8 alkoxy or halogenated C1-C8 alkoxy;

R₁₅、R₁₆、R₅₂each independently represents hydrogen, halogen, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkyl C1-C8 alkyl, C3-C8 cycloalkenyl, or C3-C8 cycloalkenyl C1-C8 alkyl, wherein said "C1-C8 alkyl", "C2-C8 alkenyl", "C2-C8 alkynyl", "C3-C8 cycloalkyl", "C3-C8 cycloalkyl C1-C8 alkyl", "C3-C8 cycloalkenyl", or "C3-C8 cycloalkenyl C1-C8 alkyl" are each independently unsubstituted or substituted by halogen.

3. A fused ring substituted aromatic compound according to claim 1 or 2,

y represents halogen, halogeno-C1-C6 alkyl, cyano, nitro or amino;

het represents a cyclic structure having 4-and 5-positions of two carbon atoms in common with the isoxazoline ring to form a fused ring, and the cyclic structure is 3-to 8-membered saturated or unsaturatedAnd carbocyclic rings or containing elements selected from O, S, N, NH, CO, SO₂Or C ═ N-O-R₁₄In which 1,2 or 3 hetero atoms in the saturated or unsaturated heterocyclic ring, except for the 4-and 5-positions, respectively, are replaced by X₂Or X₁Independently of the substitution, the other positions on the Het are each unsubstituted OR substituted by a group selected from halogen, cyano, nitro, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, haloC 1-C6 alkyl, haloC 2-C6 alkenyl, haloC 2-C6 alkynyl, haloC 3-C6 cycloalkyl, C3-C6 cycloalkyl substituted by C1-C6 alkyl, -OR₁₄、-SR₁₄、-SOR₁₄、-(CO)OR₁₄、-(SO₂)R₁₄、-N(R₁₄)₂OR-O- (CO) OR₁₄Is substituted with at least one radical group;

X₁、X₂each independently represents hydrogen, halogen, nitro, cyano, thiocyanato, hydroxyl, mercapto, sulfonic acid, formyl, haloformyl, azido, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C6 alkyl, C3-C6 cycloalkenyl, C3-C6 cycloalkenyl C1-C6 alkyl, -PO (OR')₂、-OR”、-(CO)R”、-SR”、-(SO)R”、-(SO₂)R”、-Si(R”)₃、-O(CO)R”、-O-(SO₂)R”、-S(CO)R”、-(SO₂)OR”、-O(CO)OR”、-(CO)(CO)OR”、-CR '═ N-OH, -CR' ═ N-O-R ", heterocyclyl C1-C6 alkyl, aryl C1-C6 alkyl, amino C1-C6 alkyl, aminocarbonyl C1-C6 alkyl, aminocarbonyloxy C1-C6 alkyl, aminothiocarbonyloxy C1-C6 alkyl, aminosulfonyl or aminosulfonyloxy C1-C6 alkyl, where,

said "C1-C6 alkyl", "C2-C6 alkenyl" OR "C2-C6 alkynyl" are each independently unsubstituted OR substituted with a substituent selected from the group consisting of halogen, cyano, hydroxy, mercapto, carboxyl, -OR ", (CO) R", (SR) ", - (SO)₂)R”、-O(CO)H、-O(CO)R”、-O-(SO₂) R ", - (CO) OR", -O (CO) OH, -O (CO) OR ", -O- (C1-C6 alkyl-)Substituted by 1,2 OR 3 groups of (CO) OH OR-O- (C1-C6 alkyl) - (CO) OR ",

the "C3-C6 cycloalkyl", "C3-C6 cycloalkyl C1-C6 alkyl", "C3-C6 cycloalkenyl", "C3-C6 cycloalkenyl C1-C6 alkyl", "heterocyclyl C1-C6 alkyl", "aryl" OR "aryl C1-C6 alkyl" are each independently unsubstituted OR selected from oxo, halogen, cyano, nitro, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, halo C1-C6 alkyl, halo C2-C6 alkenyl, halo C6-C6 alkynyl, halo C6-C6 cycloalkyl, C6-C6 cycloalkyl substituted by C6-C6 alkyl, -OR₁₄、-SR₁₄、-(CO)OR₁₄、-(SO₂)R₁₄、-N(R₁₄)₂OR-O- (C1-C6 alkyl) - (CO) OR₁₄Or two adjacent carbon atoms in the ring and-OCH which are unsubstituted or substituted by halogen₂CH₂-or-OCH₂O-forms a condensed ring,

the "amino", "amino C1-C6 alkyl", "aminocarbonyl C1-C6 alkyl", "aminocarbonyloxy C1-C6 alkyl", "aminothiocarbonyloxy C1-C6 alkyl", "aminosulfonyl" or "aminosulfonyloxy C1-C6 alkyl" are each independently unsubstituted or selected from the group consisting of₁₁、-OR₁₁、-(CO)R₁₁、-(CO)OR₁₁- (C1-C6 alkyl) - (CO) OR₁₁、-(SO₂)R₁₁、-(SO₂)OR₁₁- (C1-C6 alkyl) - (SO)₂)R₁₁、-(CO)N(R₁₂)₂Or- (SO)₂)N(R₁₂)₂Substituted with one or two groups;

r' independently represents hydrogen, halogen, C1-C6 alkoxy, C1-C6 alkoxy C1-C6 alkyl, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C6 alkyl, C3-C6 cycloalkenyl, C3-C6 cycloalkenyl C1-C6 alkyl, aryl C1-C6 alkyl, heterocyclyl, or heterocyclyl C1-C6 alkyl, wherein "C1-C6 alkyl", "C2-C6 alkenyl" or "C2-C6 alkynyl" independently of one another are unsubstituted or substituted by halogen, and "C3-C6 cycloalkyl", "C3-C6 cycloalkyl C1-C6 alkyl "," C3-C6 cycloalkenyl "," C3-C6 cycloalkenyl C1-C6 alkyl "," aryl C1-C6 alkyl "," heterocyclyl "OR" heterocyclyl C1-C6 alkyl "are each independently unsubstituted OR substituted by groups selected from oxo, halogen, cyano, nitro, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, halo C1-C6 alkyl, halo C2-C6 alkenyl, halo C2-C6 alkynyl, halo C3-C6 cycloalkyl, C3-C6 cycloalkyl substituted by C1-C6 alkyl, -OR₁₄、-SR₁₄、-(CO)OR₁₄、-(SO₂)R₁₄、-N(R₁₄)₂OR-O- (C1-C6 alkyl) - (CO) OR₁₄Or two adjacent carbon atoms in the ring and-OCH which are unsubstituted or substituted by halogen₂CH₂-or-OCH₂O-forms a fused ring;

r' each independently represents C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C6 alkyl, C3-C6 cycloalkenyl, C3-C6 cycloalkenyl C1-C6 alkyl, aryl C1-C6 alkyl, aryl C2-C6 alkenyl, heterocyclyl C1-C6 alkyl, OR heterocyclyl C2-C6 alkenyl, wherein each of said "C1-C6 alkyl", "C2-C6 alkenyl", OR "C2-C6 alkynyl" is independently unsubstituted OR selected from halogen, cyano, tri C1-C6 alkylsilyl, -OR₁₃、-SR₁₃、-O(CO)R₁₃、-(CO)R₁₃、-(CO)OR₁₃OR-O (CO) OR₁₃Said "C3-C6 cycloalkyl", "C3-C6 cycloalkyl C1-C6 alkyl", "C3-C6 cycloalkenyl", "C3-C6 cycloalkenyl C1-C6 alkyl", "aryl C1-C6 alkyl", "aryl C2-C6 alkenyl", "heterocyclyl C1-C6 alkyl" or "heterocyclyl C2-C6 alkenyl" each independently being unsubstituted or selected from oxo, halogen, cyano, nitro, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, halogenated C1-C6 alkyl, halogenated C2-C6 alkenyl, halogenated C2-C6 alkynyl, halogenated C3-C6 cycloalkyl, C3-C6 cycloalkyl substituted by C1-C6 alkyl, -OR.₁₄、-SR₁₄、-(CO)OR₁₄、-(SO₂)R₁₄、-N(R₁₄)₂OR-O- (C1-C6 alkyl) - (CO) OR₁₄Or two adjacent carbon atoms in the ring and-OCH which are unsubstituted or substituted by halogen₂CH₂-or-OCH₂O-forms a fused ring;

W₁represents O, S, NH or N- (C1-C6 alkyl);

W₃each independently represents hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkenyl, heterocyclyl, aryl, heteroaryl, substituted heteroaryl, Wherein each of said "C1-C6 alkyl", "C2-C6 alkenyl" or "C2-C6 alkynyl" is independently unsubstituted or selected from the group consisting of halogen, cyano, nitro, C3-C6 cycloalkyl, tri-C1-C6 alkylsilyl, C3-C6 cycloalkenyl, heterocyclyl, aryl, heteroaryl, and heteroaryl, (ii) said "C3-C6 cycloalkyl", "C3-C6 cycloalkenyl", "heterocyclyl" OR "aryl" each independently being unsubstituted OR selected from oxo, halogen, cyano, nitro, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, halogenated C1-C6 alkyl, halogenated C2-C6 alkenyl, halogenated C2-C6 alkynyl, halogenated C3-C6 cycloalkyl, C3-C6 cycloalkyl substituted with C1-C6 alkyl, -OR₁₄、-SR₁₄、-(CO)OR₁₄、-(SO₂)R₁₄、-N(R₁₄)₂OR-O- (C1-C6 alkyl) - (CO) OR₁₄Or two adjacent carbon atoms in the ring and-OCH which are unsubstituted or substituted by halogen₂CH₂-or-OCH₂O-forms a fused ring;

or N (W₃)₂RepresentsWhich is unsubstituted or substituted by 1,2 or 3 groups selected from oxo, C1-C6 alkyl or C1-C6 alkoxycarbonyl;

X₁₁each independently represents hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C6 alkyl, C6-C6 cycloalkenyl, heterocyclyl C6-C6 alkyl, aryl, or aryl C6-C6 alkyl, wherein said "C6-C6 cycloalkyl", "C6-C6 cycloalkyl C6-C6 alkyl", "C6-C6 cycloalkenyl C6-C6 alkyl", "heterocyclyl C6-C6 alkyl", "aryl", or "aryl C6-C6 alkyl" are each independently unsubstituted or selected from oxo, halogen, cyano, nitro, C6-C6 alkyl, C6-C6 alkenyl, C6-C6 alkynyl, C3-C6 cycloalkyl, halo-C1-C6 alkyl, halo-C2-C6 alkenyl, halo-C2-C6 alkynyl, halo-C3-C6 cycloalkyl, C3-C6 cycloalkyl substituted by C1-C6 alkyl, -OR₁₄、-SR₁₄、-(CO)OR₁₄、-(SO₂)R₁₄、-N(R₁₄)₂OR-O- (C1-C6 alkyl) - (CO) OR₁₄Or two adjacent carbon atoms in the ring and-OCH which are unsubstituted or substituted by halogen₂CH₂-or-OCH₂O-forms a fused ring;

X₁₂each independently represents C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C6 alkyl, C6-C6 cycloalkenyl, heterocyclyl C6-C6 alkyl, aryl, or aryl C6-C6 alkyl, wherein said "C6-C6 cycloalkyl", "C6-C6 cycloalkyl C6-C6 alkyl", "C6-C6 cycloalkenyl C6-C6 alkyl", "heterocyclyl" C6-C6 alkyl "," aryl ", or" aryl C6-C6 alkyl "are each independently unsubstituted or selected from oxo, halogen, cyano, nitro, C6-C6 alkyl, C6-C6 alkenyl, C6-C6 alkynyl, C6-C6 alkynyl, C3-C6 cycloalkyl, halo-C1-C6 alkyl, halo-C2-C6 alkenyl, halo-C2-C6 alkynyl, haloC3-C6 cycloalkyl, C3-C6 cycloalkyl substituted by C1-C6 alkyl, -OR₁₄、-SR₁₄、-(CO)OR₁₄、-(SO₂)R₁₄、-N(R₁₄)₂OR-O- (C1-C6 alkyl) - (CO) OR₁₄Or two adjacent carbon atoms in the ring and-OCH which are unsubstituted or substituted by halogen₂CH₂-or-OCH₂O-forms a fused ring;

X₁₃、X₁₄each independently represents hydrogen, halogen, cyano, C1-C6 alkoxy, C1-C6 alkoxy C1-C6 alkyl, C1-C6 alkylcarbonyl, C1-C6 alkoxycarbonyl, C1-C6 alkylsulfonyl, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C6 alkyl, C3-C6 cycloalkenyl, C3-C6 cycloalkenyl C1-C6 alkyl, aryl C1-C6 alkyl, heterocyclyl or heterocyclyl C1-C6 alkyl, or the group CX₁₃X₁₄Together form a 5-to 8-membered saturated carbocyclic ring,Or a group NX₁₃X₁₄Are formed togetherWherein each of said "C1-C6 alkyl", "C2-C6 alkenyl" or "C2-C6 alkynyl" is independently unsubstituted or substituted by halogen, and said "C3-C6 cycloalkyl", "C3-C6 cycloalkyl C1-C6 alkyl", "C3-C6 cycloalkenyl", "C3-C6 cycloalkenyl C6-C6 alkyl", "aryl C6-C6 alkyl", "heterocyclyl" or "heterocyclyl C6-C6 alkyl" is independently unsubstituted or substituted by an alkyl group selected from oxo, halogen, cyano, nitro, C6-C6 alkyl, C6-C6 alkenyl, C6-C6 alkynyl, C6-C6 cycloalkyl, haloC 6-C6 alkyl, haloC 6-C6 alkenyl, haloC 6-C6 alkynyl, haloC 6-C6 alkenyl, haloC 6-C6 cycloalkyl, C6-C6 cycloalkyl 6-C6 alkyl, C6 cycloalkyl 6-C6 alkyl, -OR₁₄、-SR₁₄、-(CO)OR₁₄、-(SO₂)R₁₄、-N(R₁₄)₂OR-O- (C1-C6 alkyl) - (CO) OR₁₄Substituted by 1,2 or 3 radicals in, or on the ringO two carbon atoms and-OCH unsubstituted or substituted by halogen₂CH₂-or-OCH₂O-forms a condensed ring, the "5-to 8-membered saturated carbocyclic ringIs unsubstituted or substituted by 1,2 or 3 radicals selected from C1-C6 alkyl, C1-C6 alkoxycarbonyl or benzyl, or forms a fused ring structure with an aryl or heterocyclic radicalIs unsubstituted or substituted by 1,2 or 3 groups selected from oxo, C1-C6 alkyl or C1-C6 alkoxycarbonyl;

R₁、R₂、R₆、R₁₀、R₁₇、R₁₈、R₂₂、R₂₅、R₃₂each independently represents hydrogen, cyano, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, formyl C1-C6 alkyl, cyano C1-C6 alkyl, amino C1-C6 alkyl, aminocarbonyl C1-C6 alkyl, aminosulfonyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C6 alkyl, C3-C6 cycloalkenyl, C3-C6 cycloalkenyl C1-C6 alkyl, heterocyclyl C1-C6 alkyl, aryl C1-C6 alkyl, R6 alkyl₄R₅N-(CO)-NR₃-、R₃-S(O)_m- (C1-C6 alkyl)_n-、R₃-O- (C1-C6 alkyl)_n-、R₃- (CO) - (C1-C6 alkyl)_n-、R₃-O- (C1-C6 alkyl)_n-(CO)-、R₃- (CO) -O- (C1-C6 alkyl)_n-、R₃-S- (CO) - (C1-C6 alkyl)_n-、R₃-O- (CO) - (C1-C6 alkyl) -or R₃-O- (CO) -O- (C1-C6 alkyl) -, wherein,

the "C1-C6 alkyl", "C2-C6 alkenyl" or "C2-C6 alkynyl" each independently is unsubstituted or substituted with halogen,

said "amino group"),"amino C1-C6 alkyl", "aminocarbonyl C1-C6 alkyl" or "aminosulfonyl" are each independently unsubstituted or selected from the group consisting of₁₁、-OR₁₁、-(CO)R₁₁、-(CO)OR₁₁- (C1-C6 alkyl) - (CO) OR₁₁、-(SO₂)R₁₁、-(SO₂)OR₁₁- (C1-C6 alkyl) - (SO)₂)R₁₁、-(CO)N(R₁₂)₂Or- (SO)₂)N(R₁₂)₂Substituted with one or two of the groups in (a),

the "C3-C6 cycloalkyl", "C3-C6 cycloalkyl C1-C6 alkyl", "C3-C6 cycloalkenyl", "C3-C6 cycloalkenyl C1-C6 alkyl", "heterocyclyl C1-C6 alkyl", "aryl" OR "aryl C1-C6 alkyl" are each independently unsubstituted OR selected from oxo, halogen, cyano, nitro, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, halo C1-C6 alkyl, halo C2-C6 alkenyl, halo C6-C6 alkynyl, halo C6-C6 cycloalkyl, C6-C6 cycloalkyl substituted by C6-C6 alkyl, -OR₁₄、-SR₁₄、-(CO)OR₁₄、-(SO₂)R₁₄、-N(R₁₄)₂OR-O- (C1-C6 alkyl) - (CO) OR₁₄Or two adjacent carbon atoms in the ring and-OCH which are unsubstituted or substituted by halogen₂CH₂-or-OCH₂O-forms a fused ring;

or R₁₇、R₁₈Together form-CH which is unsubstituted or substituted by at least one group selected from halogen, C1-C6 alkyl or haloC 1-C6 alkyl₂CH₂CH₂CH₂-or-CH₂CH₂OCH₂-；

R₃、R₄、R₅Each independently represents hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C6 alkyl, C3-C6 cycloalkenyl, C3-C6 cycloalkenyl C1-C6 alkyl, heterocyclyl C1-C6 alkyl, aryl, or aryl C1-C6 alkyl, wherein each of said "C1-C6 alkyl", "C2-C6 alkenyl" or "C2-C6 alkynyl" independently is unsubstituted or substituted by halogenSubstituted as described above for "C3-C6 cycloalkyl", "C3-C6 cycloalkyl C1-C6 alkyl", "C3-C6 cycloalkenyl", "C3-C6 cycloalkenyl C1-C6 alkyl", "heterocyclyl C1-C6 alkyl", "aryl", OR "aryl C1-C6 alkyl", each independently is unsubstituted OR selected from oxo, halogen, cyano, nitro, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, halogenated C1-C6 alkyl, halogenated C2-C6 alkenyl, halogenated C2-C6 alkynyl, halogenated C3-C6 cycloalkyl, C3-C6 cycloalkyl substituted with C1-C6 alkyl, -OR₁₄、-SR₁₄、-(CO)OR₁₄、-(SO₂)R₁₄、-N(R₁₄)₂OR-O- (C1-C6 alkyl) - (CO) OR₁₄Or two adjacent carbon atoms in the ring and-OCH which are unsubstituted or substituted by halogen₂CH₂-or-OCH₂O-forms a fused ring;

R₇、R₈、R₇’、R₈’、R₉、R₁₉、R₂₀、R₂₁、R₂₃、R₂₄、R₂₆、R₂₇、R₂₈、R₂₉、R₃₀、R₃₁、R₃₃、R₃₄、R₃₅、R₃₆、R₃₇、R₃₈、R₃₉、R₄₀、R₄₁、R₄₂、R₄₃、R₄₄、R₄₅、R₄₆、R₄₇、R₄₈、R₄₉、R₅₀、R₅₁each independently represents hydrogen, halogen, hydroxyl, sulfhydryl, formyl, hydroxyl C1-C6 alkyl, nitro, cyano, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C6 alkyl, C3-C6 cycloalkenyl, C3-C6 cycloalkenyl C1-C6 alkyl, -OR₁₁、-SR₁₁、-(SO)R₁₁、-(SO₂)R₁₁、-(SO₂)OR₁₁、-O(SO₂)R₁₁、-N(R₁₂)₂Phenyl or benzyl, wherein,

said "C1-C6 alkyl", "C2-C6 alkenyl", "C2-C6 alkynyl", "C3-C6 cycloalkyl", "C3-C6 cycloalkyl C1-C6 alkyl", "C3-C6 cycloalkenyl" or "C3-C6 cycloalkenyl C1-C6 alkyl" each independently being unsubstituted or substituted by halogen, said "phenyl" or "benzyl" each independently being unsubstituted or substituted by at least one group selected from halogen, cyano, nitro, C1-C6 alkyl, halo C1-C6 alkyl, C1-C6 alkoxycarbonyl 1-C6 alkylthio, C1-C6 alkylsulfonyl, C1-C6 alkoxy or halo C1-C6 alkoxy;

or R₇、R₈Together form-CH which is unsubstituted or substituted by at least one group selected from halogen, C1-C6 alkyl or haloC 1-C6 alkyl₂CH₂CH₂CH₂-or-CH ═ CH-;

or R₁₉、R₂₀Together form-CH which is unsubstituted or substituted by at least one group selected from halogen, C1-C6 alkyl or haloC 1-C6 alkyl₂CH₂CH₂CH₂-or-CH₂CH＝CHCH₂-；

Or R₂₁、R₂₂Together form-CH which is unsubstituted or substituted by at least one group selected from halogen, C1-C6 alkyl or haloC 1-C6 alkyl₂CH₂CH₂-、-CH₂OCH₂CH₂-or-CH₂CH₂CH₂CH₂-；

R₁₁Each independently represents C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C6 alkyl, C3-C6 cycloalkenyl, C3-C6 cycloalkenyl C1-C6 alkyl, phenyl or benzyl, wherein the "C1-C6 alkyl", "C2-C6 alkenyl", or "C2-C6 alkynyl", respectively, are independently unsubstituted or substituted with halogen, said "phenyl" or "benzyl" are each independently unsubstituted or substituted with 1,2 or 3 groups selected from halogen, cyano, nitro, C1-C6 alkyl, halo C1-C6 alkyl, C1-C6 alkoxycarbonyl, C1-C6 alkylthio, C1-C6 alkylsulfonyl, C1-C6 alkoxy or halo C1-C6 alkoxy;

R₁₂each independently represents hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 alkoxy, C1-C6 alkylsulfonylC3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C6 alkyl, C3-C6 cycloalkenyl or C3-C6 cycloalkenyl C1-C6 alkyl, or- (CO) N (R)₁₂)₂Or- (SO)₂)N(R₁₂)₂Group N (R) of (1)₁₂)₂Each independently represents Which is unsubstituted or substituted by 1,2 or 3 groups selected from oxo, C1-C6 alkyl or C1-C6 alkoxycarbonyl;

R₁₃each independently represents C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, phenyl or phenyl substituted by 1,2 or 3 groups selected from: halogen, cyano, nitro, C1-C6 alkyl, halogenated C1-C6 alkyl, C1-C6 alkoxy, halogenated C1-C6 alkoxy, C1-C6 alkoxycarbonyl, C1-C6 alkylthio, C1-C6 alkylsulfonyl or phenoxy substituted by 1,2 or 3 groups selected from halogen, cyano, nitro, C1-C6 alkyl, halogenated C1-C6 alkyl, C1-C6 alkoxy or halogenated C1-C6 alkoxy;

R₁₄each independently represents hydrogen, C1-C6 alkyl, halogenated C1-C6 alkyl, phenyl or phenyl substituted by 1,2 or 3 groups selected from halogen, cyano, nitro, C1-C6 alkyl, halogenated C1-C6 alkyl, C1-C6 alkoxycarbonyl, C1-C6 alkylthio, C1-C6 alkylsulfonyl, C1-C6 alkoxy or halogenated C1-C6 alkoxy;

R₁₅、R₁₆、R₅₂each independently represents hydrogen, halogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C6 alkyl, C3-C6 cycloalkenyl, or C3-C6 cycloalkenyl C1-C6 alkyl, wherein said "C1-C6 alkyl", "C2-C6 alkenyl", "C2-C6 alkynyl", "C3-C6 cycloalkyl", "C3-C6 cycloalkyl C1-C6 alkyl", "C3-C6 cycloalkenyl", or "C3-C6 cycloalkenyl C1-C6 alkyl" are each independently unsubstituted or substituted by halogen.

4. A fused ring substituted aromatic compound according to any one of claims 1 to 3,

X₁、X₂each independently represents hydrogen, halogen, nitro, cyano, thiocyanato, hydroxyl, mercapto, sulfonic acid, formyl, haloformyl, azido, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C3 alkyl, C3-C6 cycloalkenyl, C3-C6 cycloalkenyl C1-C3 alkyl, -PO (OR')₂、-OR”、-(CO)R”、-SR”、-(SO)R”、-(SO₂)R”、-Si(R”)₃、-O(CO)R”、-O-(SO₂)R”、-S(CO)R”、-(SO₂)OR”、-O(CO)OR”、-(CO)(CO)OR”、-CR '═ N-OH, -CR' ═ N-O-R ", heterocyclyl C1-C3 alkyl, aryl C1-C3 alkyl, amino C1-C3 alkyl, aminocarbonyl C1-C3 alkyl, aminocarbonyloxy C1-C3 alkyl, aminothiocarbonyloxy C1-C3 alkyl, aminosulfonyl or aminosulfonyloxy C1-C3 alkyl, where,

said "C1-C6 alkyl", "C2-C6 alkenyl" OR "C2-C6 alkynyl" are each independently unsubstituted OR substituted with a substituent selected from the group consisting of halogen, cyano, hydroxy, mercapto, carboxyl, -OR ", (CO) R", (SR) ", - (SO)₂)R”、-O(CO)H、-O(CO)R”、-O-(SO₂) R ", - (CO) OR", -O (CO) OH, — O (CO) OR ", -O- (C1-C3 alkyl) - (CO) OH OR-O- (C1-C3 alkyl) - (CO) OR",

the "C3-C6 cycloalkyl", "C3-C6 cycloalkyl C1-C3 alkyl", "C3-C6 cycloalkenyl", "C3-C6 cycloalkenyl C1-C3 alkyl", "heterocyclyl C1-C3 alkyl", "aryl" OR "aryl C1-C3 alkyl" are each independently unsubstituted OR selected from oxo, halogen, cyano, nitro, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, halo C1-C6 alkyl, halo C2-C6 alkenyl, halo C6-C6 alkynyl, halo C6-C6 cycloalkyl, C6-C6 cycloalkyl substituted by C6-C6 alkyl, -OR₁₄、-SR₁₄、-(CO)OR₁₄、-(SO₂)R₁₄、-N(R₁₄)₂OR-O- (C1-C3 alkyl) - (CO) OR₁₄Or two adjacent carbon atoms in the ring and-OCH which are unsubstituted or substituted by halogen₂CH₂-or-OCH₂O-forms a condensed ring,

the "amino", "amino C1-C3 alkyl", "aminocarbonyl C1-C3 alkyl", "aminocarbonyloxy C1-C3 alkyl", "aminothiocarbonyloxy C1-C3 alkyl", "aminosulfonyl" or "aminosulfonyloxy C1-C3 alkyl" are each independently unsubstituted or selected from the group consisting of₁₁、-OR₁₁、-(CO)R₁₁、-(CO)OR₁₁- (C1-C3 alkyl) - (CO) OR₁₁、-(SO₂)R₁₁、-(SO₂)OR₁₁- (C1-C3 alkyl) - (SO)₂)R₁₁、-(CO)N(R₁₂)₂Or- (SO)₂)N(R₁₂)₂Substituted with one or two groups;

r' independently represents hydrogen, halogen, C1-C6 alkoxy, C1-C6 alkoxy C1-C3 alkyl, C1-C6 alkyl, C6-C6 alkenyl, C6-C6 alkynyl, C6-C6 cycloalkyl C6 alkyl, C6-C6 cycloalkenyl C6 alkyl, aryl C6-C6 alkyl, heterocyclyl or heterocyclyl C6-C6 alkyl, wherein "C6-C6 alkyl", "C6-C6 alkenyl" or "C6-C6 alkynyl" independently represents unsubstituted or substituted by halogen, and "C6-C6 cycloalkyl", "C6-C6 alkyl", "C6-C6 cycloalkenyl" or "C6-C6 cycloalkenyl" aryl 6 "6 alkyl, "aryl C1-C3 alkyl", "heterocyclyl" OR "heterocyclyl C1-C3 alkyl" are each independently unsubstituted OR substituted by a group selected from oxo, halogen, cyano, nitro, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, halogenated C1-C6 alkyl, halogenated C2-C6 alkenyl, halogenated C2-C6 alkynyl, halogenated C3-C6 cycloalkyl, C3-C6 cycloalkyl substituted by C1-C6 alkyl, -OR₁₄、-SR₁₄、-(CO)OR₁₄、-(SO₂)R₁₄、-N(R₁₄)₂or-O- (C1-C3 alkyl)-(CO)OR₁₄Or two adjacent carbon atoms in the ring and-OCH which are unsubstituted or substituted by halogen₂CH₂-or-OCH₂O-forms a fused ring;

r' each independently represents C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C3 alkyl, C3-C6 cycloalkenyl, C3-C6 cycloalkenyl C1-C3 alkyl, aryl C1-C3 alkyl, aryl C2-C3 alkenyl, heterocyclyl C1-C3 alkyl, OR heterocyclyl C2-C3 alkenyl, wherein each of said "C1-C6 alkyl", "C2-C6 alkenyl", OR "C2-C6 alkynyl" is independently unsubstituted OR selected from halogen, cyano, tri C1-C6 alkylsilyl, -OR₁₃、-SR₁₃、-O(CO)R₁₃、-(CO)R₁₃、-(CO)OR₁₃OR-O (CO) OR₁₃Said "C3-C6 cycloalkyl", "C3-C6 cycloalkyl C1-C3 alkyl", "C3-C6 cycloalkenyl", "C3-C6 cycloalkenyl C1-C3 alkyl", "aryl C1-C3 alkyl", "aryl C2-C3 alkenyl", "heterocyclyl C1-C3 alkyl" or "heterocyclyl C2-C3 alkenyl" each independently being unsubstituted or selected from oxo, halogen, cyano, nitro, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, halogenated C1-C6 alkyl, halogenated C2-C6 alkenyl, halogenated C2-C6 alkynyl, halogenated C3-C6 cycloalkyl, C3-C6 cycloalkyl substituted by C1-C6 alkyl, -OR.₁₄、-SR₁₄、-(CO)OR₁₄、-(SO₂)R₁₄、-N(R₁₄)₂OR-O- (C1-C3 alkyl) - (CO) OR₁₄Or two adjacent carbon atoms in the ring and-OCH which are unsubstituted or substituted by halogen₂CH₂-or-OCH₂O-forms a fused ring;

W₃each independently represents hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkenyl, heterocyclyl, aryl, heteroaryl, substituted heteroaryl, Wherein each of said "C1-C6 alkyl", "C2-C6 alkenyl" or "C2-C6 alkynyl" is independently unsubstituted or selected from the group consisting of halogen, cyano, nitro, C3-C6 cycloalkyl, tri-C1-C6 alkylsilyl, C3-C6 cycloalkenyl, heterocyclyl, aryl, heteroaryl, and heteroaryl, (ii) said "C3-C6 cycloalkyl", "C3-C6 cycloalkenyl", "heterocyclyl" OR "aryl" each independently being unsubstituted OR selected from oxo, halogen, cyano, nitro, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, halogenated C1-C6 alkyl, halogenated C2-C6 alkenyl, halogenated C2-C6 alkynyl, halogenated C3-C6 cycloalkyl, C3-C6 cycloalkyl substituted with C1-C6 alkyl, -OR₁₄、-SR₁₄、-(CO)OR₁₄、-(SO₂)R₁₄、-N(R₁₄)₂OR-O- (C1-C3 alkyl) - (CO) OR₁₄Or two adjacent carbon atoms in the ring and-OCH which are unsubstituted or substituted by halogen₂CH₂-or-OCH₂O-forms a fused ring;

or N (W)₃)₂RepresentsWhich is unsubstituted or substituted by 1,2 or 3 groups selected from oxo, C1-C6 alkyl or C1-C6 alkoxycarbonyl;

X₁₁each independently represents hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C3 alkyl, C3-C6 cycloalkenyl, C3-C6 cycloalkenyl C1-C3 alkyl, heterocyclyl C1-C3 alkyl, aryl or aryl C1-C3 alkyl, wherein the "C3-C6 cycloalkyl", "C3-C6 cycloalkyl C1-C3 alkyl", "C3-C6 cycloalkenyl", "C3-C6 cycloalkenylThe radicals C1-C3 alkyl "," heterocyclyl C1-C3 alkyl "," aryl "OR" arylC 1-C3 alkyl "are each independently unsubstituted OR selected from oxo, halogen, cyano, nitro, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, haloC 1-C6 alkyl, haloC 2-C6 alkenyl, haloC 2-C6 alkynyl, haloC 3-C6 cycloalkyl, C3-C6 cycloalkyl substituted by C1-C6 alkyl, -OR₁₄、-SR₁₄、-(CO)OR₁₄、-(SO₂)R₁₄、-N(R₁₄)₂OR-O- (C1-C3 alkyl) - (CO) OR₁₄Or two adjacent carbon atoms in the ring and-OCH which are unsubstituted or substituted by halogen₂CH₂-or-OCH₂O-forms a fused ring;

X₁₂each independently represents C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C3 alkyl, C3-C3 cycloalkenyl, heterocyclyl C3-C3 alkyl, aryl, or aryl C3-C3 alkyl, wherein said "C3-C3 cycloalkyl", "C3-C3 cycloalkyl C3-C3 alkyl", "C3-C3 cycloalkenyl C3-C3 alkyl", "heterocyclyl" C3-C3 alkyl "," aryl ", or" aryl C3-C3 alkyl "are each independently unsubstituted or selected from oxo, halogen, cyano, nitro, C3-C3 alkyl, C3-C3 alkenyl, C3-C3 alkynyl, C3-C3 alkynyl, C3-C6 cycloalkyl, halo-C1-C6 alkyl, halo-C2-C6 alkenyl, halo-C2-C6 alkynyl, halo-C3-C6 cycloalkyl, C3-C6 cycloalkyl substituted by C1-C6 alkyl, -OR₁₄、-SR₁₄、-(CO)OR₁₄、-(SO₂)R₁₄、-N(R₁₄)₂OR-O- (C1-C3 alkyl) - (CO) OR₁₄Or two adjacent carbon atoms in the ring and-OCH which are unsubstituted or substituted by halogen₂CH₂-or-OCH₂O-forms a fused ring;

X₁₃、X₁₄each independently represents hydrogen, halogen, cyano, C1-C6 alkoxy, C1-C6 alkoxy C1-C3 alkyl, C1-C6 alkylcarbonyl, C1-C6 alkoxycarbonyl, C1-C6 alkylsulfonyl, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynylC3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C3 alkyl, C3-C6 cycloalkenyl, C3-C6 cycloalkenyl C1-C3 alkyl, aryl C1-C3 alkyl, heterocyclyl or heterocyclyl C1-C3 alkyl, or the group CX₁₃X₁₄Together form a 5-to 8-membered saturated carbocyclic ring,Or a group NX₁₃X₁₄Are formed togetherWherein each of said "C1-C6 alkyl", "C2-C6 alkenyl" or "C2-C6 alkynyl" is independently unsubstituted or substituted by halogen, and said "C3-C6 cycloalkyl", "C3-C6 cycloalkyl C1-C3 alkyl", "C3-C6 cycloalkenyl", "C3-C6 cycloalkenyl C6-C6 alkyl", "aryl C6-C6 alkyl", "heterocyclyl" or "heterocyclyl C6-C6 alkyl" is independently unsubstituted or substituted by an alkyl group selected from oxo, halogen, cyano, nitro, C6-C6 alkyl, C6-C6 alkenyl, C6-C6 alkynyl, C6-C6 cycloalkyl, haloC 6-C6 alkyl, haloC 6-C6 alkenyl, haloC 6-C6 alkynyl, haloC 6-C6 alkenyl, haloC 6-C6 cycloalkyl, C6-C6 cycloalkyl 6-C6 alkyl, C6 cycloalkyl 6-C6 alkyl, -OR₁₄、-SR₁₄、-(CO)OR₁₄、-(SO₂)R₁₄、-N(R₁₄)₂OR-O- (C1-C3 alkyl) - (CO) OR₁₄Or two adjacent carbon atoms in the ring and-OCH which are unsubstituted or substituted by halogen₂CH₂-or-OCH₂O-forms a condensed ring, the "5-to 8-membered saturated carbocyclic ringIs unsubstituted or substituted by 1,2 or 3 groups selected from C1-C6 alkyl, C1-C6 alkoxycarbonyl or benzyl, or forms a fused ring structure with phenyl or thienyl; the above-mentionedIs unsubstituted or selected from oxo, C1-C6 alkyl or C1-C6 alkylSubstituted by 1,2 or 3 groups of the oxycarbonyl group;

R₁₁each independently represents C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C3 alkyl, C3-C6 cycloalkenyl, C3-C6 cycloalkenyl C1-C3 alkyl, phenyl, benzyl, wherein the "C1-C6 alkyl", "C2-C6 alkenyl", or "C2-C6 alkynyl", respectively, are independently unsubstituted or substituted with halogen, said "phenyl" or "benzyl" are each independently unsubstituted or substituted with 1,2 or 3 groups selected from halogen, cyano, nitro, C1-C6 alkyl, halo C1-C6 alkyl, C1-C6 alkoxycarbonyl, C1-C6 alkylthio, C1-C6 alkylsulfonyl, C1-C6 alkoxy or halo C1-C6 alkoxy;

R₁₂each independently represents hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 alkoxy, C1-C6 alkylsulfonyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C3 alkyl, C3-C6 cycloalkenyl or C3-C6 cycloalkenyl C1-C3 alkyl, or- (CO) N (R) N₁₂)₂Or- (SO)₂)N(R₁₂)₂Group N (R) of (1)₁₂)₂Each independently represents Which is unsubstituted or substituted by 1,2 or 3 groups selected from oxo, C1-C6 alkyl or C1-C6 alkoxycarbonyl;

R₁₃each independently represents C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, phenyl or phenyl substituted by 1,2 or 3 groups selected from: halogen, cyano, nitro, C1-C6 alkyl, halogenated C1-C6 alkyl, C1-C6 alkoxy, halogenated C1-C6 alkoxy, C1-C6 alkoxycarbonyl, C1-C6 alkylthio, C1-C6 alkylsulfonyl or phenoxy substituted by 1,2 or 3 groups selected from halogen, cyano, nitro, C1-C6 alkyl, halogenated C1-C6 alkyl, C1-C6 alkoxy or halogenated C1-C6 alkoxy;

R₁₄each independently of the other represents hydrogen,C1-C6 alkyl, halogenated C1-C6 alkyl, phenyl or phenyl substituted by 1,2 or 3 groups selected from halogen, cyano, nitro, C1-C6 alkyl, halogenated C1-C6 alkyl, C1-C6 alkoxycarbonyl, C1-C6 alkylthio, C1-C6 alkylsulfonyl, C1-C6 alkoxy or halogenated C1-C6 alkoxy;

preferably, it is selected from any one of table 1.

5. A fused ring substituted aromatic compound according to any one of claims 1 to 4,

het represents Except that the 4-and 5-positions in formula I are each independently replaced by X₂Or X₁Independently of the substitution, the other positions on the Het are each unsubstituted OR substituted by a group selected from halogen, cyano, nitro, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, haloC 1-C6 alkyl, haloC 2-C6 alkenyl, haloC 2-C6 alkynyl, haloC 3-C6 cycloalkyl, C3-C6 cycloalkyl substituted by C1-C6 alkyl, -OR₁₄、-SR₁₄、-SOR₁₄、-(CO)OR₁₄、-(SO₂)R₁₄、-N(R₁₄)₂OR-O- (C1-C3 alkyl) - (CO) OR₁₄1,2 or 3 groups of (a).

6. A fused ring substituted aromatic compound according to any one of claims 1 to 5,

q represents

7. A method of preparing a fused ring substituted aromatic compound as claimed in any one of claims 1 to 6, comprising the steps of:

a compound of the formula IIConverting into a compound shown as a general formula I; substituent X₁、X₂Het, Q, Y, Z and M are as defined in claims 1 to 6.

8. A herbicidal composition comprising a herbicidally effective amount of at least one of the fused ring substituted aromatic compounds of any one of claims 1 to 6, preferably further comprising formulation adjuvants.

9. A method of controlling weeds, comprising applying a herbicidally effective amount of at least one of the fused ring substituted aromatic compounds of any one of claims 1 to 6 or the herbicidal composition of claim 8 to a plant or to a weed locus.

10. Use of at least one of the fused ring substituted aromatic compounds of any one of claims 1 to 6 or the herbicidal composition of claim 8 for controlling weeds, preferably in crops of useful plants, said crops being transgenic or treated with genome editing technology.

Background

The control of weeds is a crucial link in the realization of efficient agricultural processes, despite the variety of herbicides on the market, for example patent WO00/50409 and the like disclose the use of 1-aryl-4-thiotriazines of the general formula as herbicides; CN105753853A discloses an isoxazoline-containing uracil compound and its use as a herbicide. However, the herbicidal properties of these known compounds against harmful plants and the selectivity for crop plants are not entirely satisfactory. And due to the continuous expansion of the market, the resistance of weeds, the service life of drugs, the economic efficiency of drugs and the like and the increasing attention of people to the environment, scientists are required to continuously research and develop new herbicide varieties with high efficiency, safety, economy and different action modes.

Disclosure of Invention

The present invention provides a condensed ring-substituted aromatic compound having excellent herbicidal activity against grassy weeds, broadleaf weeds, etc. and high selectivity for crops even at low application rates, a preparation method thereof, a herbicidal composition, and applications thereof.

The technical scheme adopted by the invention is as follows:

a fused ring substituted aromatic compound is shown in a general formula I:

wherein the content of the first and second substances,

q represents

Y represents halogen, haloalkyl, cyano, nitro or amino;

z represents hydrogen, halogen or hydroxy;

m represents CH or N;

Q₁、Q₂、Q₃、Q₄、Q₅、Q₆each independently represents O or S;

het represents a cyclic structure sharing two carbon atoms at 4-and 5-positions with the isoxazoline ring to form a fused ring, the cyclic structure being a 3-to 8-membered saturated or unsaturated carbocyclic ring or containing a group selected from O, S, N, NH, CO, SO₂Or C ═ N-O-R₁₄In which 1,2 or 3 hetero atoms in the saturated or unsaturated heterocyclic ring, except for the 4-and 5-positions, respectively, are replaced by X₂Or X₁Independently of each other on said Het, is unsubstituted or substituted by one or more substituents selected from halogen, cyano, nitro, alkyl, alkenyl, alkynyl, cycloalkyl, haloalkyl, haloalkenyl, haloalkynyl, haloCycloalkyl, cycloalkyl substituted by alkyl, -OR₁₄、-SR₁₄、-SOR₁₄、-(CO)OR₁₄、-(SO₂)R₁₄、-N(R₁₄)₂OR-O- (CO) OR₁₄Is substituted with at least one radical group;

X₁、X₂each independently represents hydrogen, halogen, nitro, cyano, thiocyanato, hydroxyl, mercapto, sulfonic acid, formyl, haloformyl, azido, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl, cycloalkenylalkyl, -PO (OR')₂、-OR”、-(CO)R”、-SR”、-(SO)R”、-(SO₂)R”、-Si(R”)₃、-O(CO)R”、-O-(SO₂)R”、-S(CO)R”、-(SO₂)OR”、-O(CO)OR”、-(CO)(CO)OR”、-CR '═ N-OH, -CR' ═ N-O-R ", heterocyclyl, heterocyclylalkyl, aryl, arylalkyl, amino, aminoalkyl, aminocarbonylalkyl, aminocarbonyloxyalkyl, aminothiocarbonyloxyalkyl, aminosulfonyl or aminosulfonyloxyalkyl, where,

said "alkyl", "alkenyl" OR "alkynyl" are each independently unsubstituted OR selected from halogen, cyano, hydroxy, mercapto, carboxyl, -OR ", (CO) R", -SR ", (SO)₂)R”、-O(CO)H、-O(CO)R”、-O-(SO₂) R ", - (CO) OR", -O (CO) OH, — O (CO) OR ", -O-alkyl- (CO) OH OR-O-alkyl- (CO) OR",

said "cycloalkyl", "cycloalkylalkyl", "cycloalkenyl", "cycloalkenylalkyl", "heterocyclyl", "heterocyclylalkyl", "aryl", OR "arylalkyl" are each independently unsubstituted OR substituted with a group selected from oxo, halogen, cyano, nitro, alkyl, alkenyl, alkynyl, cycloalkyl, haloalkyl, haloalkenyl, haloalkynyl, halocycloalkyl, cycloalkyl substituted with alkyl, -OR₁₄、-SR₁₄、-(CO)OR₁₄、-(SO₂)R₁₄、-N(R₁₄)₂OR-O-alkyl- (CO) OR₁₄Or two adjacent carbon atoms in the ring and-OCH which are unsubstituted or substituted by halogen₂CH₂-or-OCH₂O-forms a condensed ring,

said "amino", "aminoalkyl", "aminocarbonylalkyl", "aminocarbonyloxyalkyl", "aminothiocarbonyloxyalkyl", "aminosulfonyl" or "aminosulfonyloxyalkyl" groups are each independently unsubstituted or selected from-R₁₁、-OR₁₁、-(CO)R₁₁、-(CO)OR₁₁-alkyl- (CO) OR₁₁、-(SO₂)R₁₁、-(SO₂)OR₁₁-alkyl- (SO)₂)R₁₁、-(CO)N(R₁₂)₂Or- (SO)₂)N(R₁₂)₂Substituted with one or two groups;

r' each independently represents hydrogen, halogen, alkoxy, alkoxyalkyl, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl, cycloalkenylalkyl, aryl, arylalkyl, heterocyclyl, OR heterocyclylalkyl, wherein the "alkyl", "alkenyl", OR "alkynyl" each independently is unsubstituted OR substituted with halogen, and the "cycloalkyl", "cycloalkylalkyl", "cycloalkenyl", "cycloalkenylalkyl", "aryl", "arylalkyl", "heterocyclyl", OR "heterocyclylalkyl" each independently is unsubstituted OR selected from oxo, halogen, cyano, nitro, alkyl, alkenyl, alkynyl, cycloalkyl, haloalkyl, haloalkenyl, haloalkynyl, halocycloalkyl, alkyl-substituted cycloalkyl, -OR₁₄、-SR₁₄、-(CO)OR₁₄、-(SO₂)R₁₄、-N(R₁₄)₂OR-O-alkyl- (CO) OR₁₄Or two adjacent carbon atoms in the ring and-OCH which are unsubstituted or substituted by halogen₂CH₂-or-OCH₂O-forms a fused ring;

r' independently represents alkyl, alkenyl, alkynyl,Cycloalkyl, cycloalkylalkyl, cycloalkenyl, cycloalkenylalkyl, aryl, arylalkyl, arylalkenyl, heterocyclyl, heterocyclylalkyl, OR heterocyclylalkenyl, wherein the "alkyl", "alkenyl", OR "alkynyl" groups are each independently unsubstituted OR selected from halogen, cyano, trialkylsilyl, -OR₁₃、-SR₁₃、-O(CO)R₁₃、-(CO)R₁₃、-(CO)OR₁₃OR-O (CO) OR₁₃Each of said "cycloalkyl", "cycloalkylalkyl", "cycloalkenyl", "cycloalkenylalkyl", "aryl", "arylalkyl", "arylalkenyl", "heterocyclyl", "heterocyclylalkyl", OR "heterocyclylalkenyl" is independently unsubstituted OR substituted with at least one group selected from oxo, halogen, cyano, nitro, alkyl, alkenyl, alkynyl, cycloalkyl, haloalkyl, haloalkenyl, haloalkynyl, halocycloalkyl, cycloalkyl substituted with alkyl, -OR₁₄、-SR₁₄、-(CO)OR₁₄、-(SO₂)R₁₄、-N(R₁₄)₂OR-O-alkyl- (CO) OR₁₄Or two adjacent carbon atoms in the ring and-OCH which are unsubstituted or substituted by halogen₂CH₂-or-OCH₂O-forms a fused ring;

W₁represents O, S, NH or N-alkyl;

W₂represents OW₃、SW₃Or N (W)₃)₂；

W₃Each independently represents hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, heterocyclyl, aryl, heterocyclyl, or heterocyclyl, Wherein each of said "alkyl", "alkenyl" or "alkynyl" is independently unsubstituted or selectedFrom halogen, cyano, nitro, cycloalkyl, trialkylsilyl, cycloalkenyl, heterocyclyl, aryl, heterocyclyl, heteroaryl, substituted heteroaryl, or substituted heteroaryl, Each of said "cycloalkyl", "cycloalkenyl", "heterocyclyl" OR "aryl" is independently unsubstituted OR substituted with at least one group selected from oxo, halogen, cyano, nitro, alkyl, alkenyl, alkynyl, cycloalkyl, haloalkyl, haloalkenyl, haloalkynyl, halocycloalkyl, cycloalkyl substituted with alkyl, -OR₁₄、-SR₁₄、-(CO)OR₁₄、-(SO₂)R₁₄、-N(R₁₄)₂OR-O-alkyl- (CO) OR₁₄Or two adjacent carbon atoms in the ring and-OCH which are unsubstituted or substituted by halogen₂CH₂-or-OCH₂O-forms a fused ring;

or N (W)₃)₂Represents an unsubstituted or substituted heterocyclic group having a nitrogen atom at the 1-position;

X₁₁each independently represents hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl, cycloalkenylalkyl, heterocyclyl, heterocyclylalkyl, aryl, OR arylalkyl, wherein the "cycloalkyl", "cycloalkylalkyl", "cycloalkenyl", "cycloalkenylalkyl", "heterocyclyl", "heterocyclylalkyl", "aryl", OR "arylalkyl" each independently is unsubstituted OR selected from oxo, halogen, cyano, nitro, alkyl, alkenyl, alkynyl, cycloalkyl, haloalkyl, haloalkenyl, haloalkynyl, halocycloalkyl, cycloalkyl substituted with alkyl, -OR₁₄、-SR₁₄、-(CO)OR₁₄、-(SO₂)R₁₄、-N(R₁₄)₂OR-O-alkyl- (CO) OR₁₄Or two adjacent carbon atoms in the ring and-OCH which are unsubstituted or substituted by halogen₂CH₂-or-OCH₂O-forms a fused ring;

X₁₂each independently represents an alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl, cycloalkenylalkyl, heterocyclyl, heterocyclylalkyl, aryl, OR arylalkyl group, wherein the "cycloalkyl", "cycloalkylalkyl", "cycloalkenyl", "cycloalkenylalkyl", "heterocyclyl", "heterocyclylalkyl", "aryl", OR "arylalkyl" groups are each independently unsubstituted OR selected from oxo, halogen, cyano, nitro, alkyl, alkenyl, alkynyl, cycloalkyl, haloalkyl, haloalkenyl, haloalkynyl, halocycloalkyl, cycloalkyl substituted with alkyl, -OR₁₄、-SR₁₄、-(CO)OR₁₄、-(SO₂)R₁₄、-N(R₁₄)₂OR-O-alkyl- (CO) OR₁₄Or two adjacent carbon atoms in the ring and-OCH which are unsubstituted or substituted by halogen₂CH₂-or-OCH₂O-forms a fused ring;

X₁₃、X₁₄each independently represents hydrogen, halogen, cyano, alkoxy, alkoxyalkyl, alkylcarbonyl, alkoxycarbonyl, alkylsulfonyl, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl, cycloalkenylalkyl, aryl, arylalkyl, heterocyclyl or heterocyclylalkyl, or the group CX₁₃X₁₄Together forming an unsubstituted or substituted cyclic structure, or a group NX₁₃X₁₄Together form an unsubstituted OR substituted heterocyclyl group having a nitrogen atom at the 1-position, wherein "alkyl", "alkenyl" OR "alkynyl" are each independently unsubstituted OR substituted with halogen and "cycloalkyl", "cycloalkylalkyl", "cycloalkenyl", "cycloalkenylalkyl", "aryl", "arylalkyl", "heterocyclyl" OR "heterocyclylalkyl" are each independently unsubstituted OR substituted with a group selected from oxo, halogen, cyano, nitro, alkyl, alkenyl, alkynyl, cycloalkyl, haloalkyl, haloalkenyl, haloalkynyl, halocycloalkyl, cycloalkyl substituted with alkyl, -OR₁₄、-SR₁₄、-(CO)OR₁₄、-(SO₂)R₁₄、-N(R₁₄)₂OR-O-alkyl- (CO) OR₁₄Or two adjacent carbon atoms in the ring and-OCH which are unsubstituted or substituted by halogen₂CH₂-or-OCH₂O-forms a fused ring;

R₁、R₂、R₆、R₁₀、R₁₇、R₁₈、R₂₂、R₂₅、R₃₂each independently represents hydrogen, cyano, alkyl, alkenyl, alkynyl, formylalkyl, cyanoalkyl, amino, aminoalkyl, aminocarbonyl, aminocarbonylalkyl, aminosulfonyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl, cycloalkenylalkyl, heterocyclyl, heterocyclylalkyl, aryl, arylalkyl, R₄R₅N-(CO)-NR₃-、R₃-S(O)_m- (alkyl)_n-、R₃-O- (alkyl)_n-、R₃- (CO) - (alkyl)_n-、R₃-O- (alkyl)_n-(CO)-、R₃- (CO) -O- (alkyl)_n-、R₃-S- (CO) - (alkyl)_n-、R₃-O- (CO) -alkyl-or R₃-O- (CO) -O-alkyl-, wherein,

each of said "alkyl", "alkenyl" or "alkynyl" is independently unsubstituted or substituted with halogen,

said "amino", "aminoalkyl", "aminocarbonyl", "aminocarbonylalkyl" or "aminosulfonyl" are each independently unsubstituted or selected from-R₁₁、-OR₁₁、-(CO)R₁₁、-(CO)OR₁₁-alkyl- (CO) OR₁₁、-(SO₂)R₁₁、-(SO₂)OR₁₁-alkyl- (SO)₂)R₁₁、-(CO)N(R₁₂)₂Or- (SO)₂)N(R₁₂)₂Substituted with one or two of the groups in (a),

said "cycloalkyl", "cycloalkylalkyl", "cycloalkenyl"Each "cycloalkenylalkyl", "heterocyclyl", "heterocyclylalkyl", "aryl", OR "arylalkyl" is independently unsubstituted OR substituted with a group selected from oxo, halogen, cyano, nitro, alkyl, alkenyl, alkynyl, cycloalkyl, haloalkyl, haloalkenyl, haloalkynyl, halocycloalkyl, cycloalkyl substituted with alkyl, -OR₁₄、-SR₁₄、-(CO)OR₁₄、-(SO₂)R₁₄、-N(R₁₄)₂OR-O-alkyl- (CO) OR₁₄Or two adjacent carbon atoms in the ring and-OCH which are unsubstituted or substituted by halogen₂CH₂-or-OCH₂O-forms a fused ring;

or R₁₇、R₁₈Together form-CH which is unsubstituted or substituted by at least one group selected from halogen, alkyl or haloalkyl₂CH₂CH₂CH₂-or-CH₂CH₂OCH₂-；

R₃、R₄、R₅Each independently represents hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl, cycloalkenylalkyl, heterocyclyl, heterocyclylalkyl, aryl, OR arylalkyl, wherein the "alkyl", "alkenyl", OR "alkynyl" each independently is unsubstituted OR substituted with halogen, and the "cycloalkyl", "cycloalkylalkyl", "cycloalkenyl", "cycloalkenylalkyl", "heterocyclyl", "heterocyclylalkyl", "aryl", OR "arylalkyl" each independently is unsubstituted OR substituted with a group selected from oxo, halogen, cyano, nitro, alkyl, alkenyl, alkynyl, cycloalkyl, haloalkyl, haloalkenyl, haloalkynyl, halocycloalkyl, cycloalkyl substituted with alkyl, -OR₁₄、-SR₁₄、-(CO)OR₁₄、-(SO₂)R₁₄、-N(R₁₄)₂OR-O-alkyl- (CO) OR₁₄Or two adjacent carbon atoms in the ring and-OCH which are unsubstituted or substituted by halogen₂CH₂-or-OCH₂O-forms a fused ring;

R₇、R₈、R₇ ^'、R₈ ^'、R₉、R₁₉、R₂₀、R₂₁、R₂₃、R₂₄、R₂₆、R₂₇、R₂₈、R₂₉、R₃₀、R₃₁、R₃₃、R₃₄、R₃₅、R₃₆、R₃₇、R₃₈、R₃₉、R₄₀、R₄₁、R₄₂、R₄₃、R₄₄、R₄₅、R₄₆、R₄₇、R₄₈、R₄₉、R₅₀、R₅₁each independently represents hydrogen, halogen, hydroxy, mercapto, formyl, hydroxyalkyl, nitro, cyano, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl, cycloalkenylalkyl, -OR₁₁、-SR₁₁、-(SO)R₁₁、-(SO₂)R₁₁、-(SO₂)OR₁₁、-O(SO₂)R₁₁、-N(R₁₂)₂Phenyl or benzyl, wherein,

said "alkyl", "alkenyl", "alkynyl", "cycloalkyl", "cycloalkylalkyl", "cycloalkenyl" or "cycloalkenylalkyl" each independently being unsubstituted or substituted with halogen, said "phenyl" or "benzyl" each independently being unsubstituted or substituted with at least one group selected from halogen, cyano, nitro, alkyl, haloalkyl, alkoxycarbonyl, alkylthio, alkylsulfonyl, alkoxy or haloalkoxy;

or R₇、R₈Together form-CH which is unsubstituted or substituted by at least one group selected from halogen, alkyl or haloalkyl₂CH₂CH₂CH₂-or-CH ═ CH-;

or R₁₉、R₂₀Together form-CH which is unsubstituted or substituted by at least one group selected from halogen, alkyl or haloalkyl₂CH₂CH₂CH₂-or-CH₂CH＝CHCH₂-；

Or R₂₁、R₂₂Together form-CH which is unsubstituted or substituted by at least one group selected from halogen, alkyl or haloalkyl₂CH₂CH₂-、-CH₂OCH₂CH₂-or-CH₂CH₂CH₂CH₂-；

R₁₁Each independently represents an alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl, cycloalkenylalkyl, phenyl, or benzyl group, wherein the "alkyl", "alkenyl", or "alkynyl" groups are each independently unsubstituted or substituted with halogen, and the "phenyl" or "benzyl" groups are each independently unsubstituted or substituted with at least one group selected from halogen, cyano, nitro, alkyl, haloalkyl, alkoxycarbonyl, alkylthio, alkylsulfonyl, alkoxy, or haloalkoxy;

R₁₂each independently represents hydrogen, alkyl, alkenyl, alkynyl, alkoxy, alkylsulfonyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl or cycloalkenylalkyl, or- (CO) N (R)₁₂)₂Or- (SO)₂)N(R₁₂)₂Group N (R) of (1)₁₂)₂Each independently represents an unsubstituted or substituted heterocyclic group having a nitrogen atom at the 1-position;

R₁₃each independently represents an alkyl, alkenyl, alkynyl, cycloalkyl, phenyl or phenyl substituted by at least one group selected from: halogen, cyano, nitro, alkyl, haloalkyl, alkoxy, haloalkoxy, alkoxycarbonyl, alkylthio, alkylsulfonyl or phenoxy substituted by at least one group selected from halogen, cyano, nitro, alkyl, haloalkyl, alkoxy or haloalkoxy;

R₁₄each independently represents hydrogen, alkyl, haloalkyl, phenyl or phenyl substituted by at least one group selected from halogen, cyano, nitro, alkyl, haloalkyl, alkoxycarbonyl, alkylthio, alkylsulfonyl, alkoxy or haloalkoxy;

R₁₅、R₁₆、R₅₂each independently represents hydrogen, halogen, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl, or cycloalkenylalkyl, wherein the "alkyl", "alkenyl", "alkynyl", "cycloalkyl", "cycloalkylalkyl", "cycloalkenyl", or "cycloalkenylalkyl" each independently is unsubstituted or substituted with halogen;

m represents 0,1 or 2; n independently represents 0 or 1.

Preferably, Y represents halogen, halogeno-C1-C8 alkyl, cyano, nitro or amino;

het represents a cyclic structure sharing two carbon atoms at 4-and 5-positions with the isoxazoline ring to form a fused ring, the cyclic structure being a 3-to 8-membered saturated or unsaturated carbocyclic ring or containing a group selected from O, S, N, NH, CO, SO₂Or C ═ N-O-R₁₄In which 1,2 or 3 hetero atoms in the saturated or unsaturated heterocyclic ring, except for the 4-and 5-positions, respectively, are replaced by X₂Or X₁Independently of the substitution, the other positions on the Het are each unsubstituted OR substituted by a group selected from halogen, cyano, nitro, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, haloC 1-C8 alkyl, haloC 2-C8 alkenyl, haloC 2-C8 alkynyl, haloC 3-C8 cycloalkyl, C3-C8 cycloalkyl substituted by C1-C8 alkyl, -OR₁₄、-SR₁₄、-SOR₁₄、-(CO)OR₁₄、-(SO₂)R₁₄、-N(R₁₄)₂OR-O- (CO) OR₁₄Is substituted with at least one radical group;

X₁、X₂each independently represents hydrogen, halogen, nitro, cyano, thiocyanato, hydroxyl, mercapto, sulfonic acid, formyl, haloformyl, azido, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkyl C1-C8 alkyl, C3-C8 cycloalkenyl, C3-C8 cycloalkenyl C1-C8 alkyl, -PO (OR')₂、-OR”、-(CO)R”、-SR”、-(SO)R”、-(SO₂)R”、-Si(R”)₃、-O(CO)R”、-O-(SO₂)R”、-S(CO)R”、-(SO₂)OR”、-O(CO)OR”、-(CO)(CO)OR”、-CR '═ N-OH, -CR' ═ N-O-R ", heterocyclyl C1-C8 alkyl, aryl C1-C8 alkyl, amino C1-C8 alkyl, aminocarbonyl C1-C8 alkyl, aminocarbonyloxy C1-C8 alkyl, aminothiocarbonyloxy C1-C8 alkyl, aminosulfonyl or aminosulfonyloxy C1-C8 alkyl, where,

said "C1-C8 alkyl", "C2-C8 alkenyl" OR "C2-C8 alkynyl" are each independently unsubstituted OR substituted with a substituent selected from the group consisting of halogen, cyano, hydroxy, mercapto, carboxyl, -OR ", (CO) R", (SR) ", - (SO)₂)R”、-O(CO)H、-O(CO)R”、-O-(SO₂) R ", - (CO) OR", -O (CO) OH, — O (CO) OR ", -O- (C1-C8 alkyl) - (CO) OH OR-O- (C1-C8 alkyl) - (CO) OR",

the "C3-C8 cycloalkyl", "C3-C8 cycloalkyl C1-C8 alkyl", "C3-C8 cycloalkenyl", "C3-C8 cycloalkenyl C1-C8 alkyl", "heterocyclyl C1-C8 alkyl", "aryl" OR "aryl C1-C8 alkyl" are each independently unsubstituted OR selected from oxo, halogen, cyano, nitro, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, halo C1-C8 alkyl, halo C2-C8 alkenyl, halo C8-C8 alkynyl, halo C8-C8 cycloalkyl, C8-C8 cycloalkyl substituted by C8-C8 alkyl, -OR₁₄、-SR₁₄、-(CO)OR₁₄、-(SO₂)R₁₄、-N(R₁₄)₂OR-O- (C1-C8 alkyl) - (CO) OR₁₄Or two adjacent carbon atoms in the ring and-OCH which are unsubstituted or substituted by halogen₂CH₂-or-OCH₂O-forms a condensed ring,

the "amino", "amino C1-C8 alkyl", "aminocarbonyl C1-C8 alkyl", "aminocarbonyloxy C1-C8 alkyl", "aminothiocarbonyloxy C1-C8 alkyl", "aminosulfonyl" or "aminosulfonyloxy C1-C8 alkyl" are each independently unsubstituted or selected from the group consisting of₁₁、-OR₁₁、-(CO)R₁₁、-(CO)OR₁₁- (C1-C8 alkyl) - (CO) OR₁₁、-(SO₂)R₁₁、-(SO₂)OR₁₁- (C1-C8 alkyl) - (SO)₂)R₁₁、-(CO)N(R₁₂)₂Or- (SO)₂)N(R₁₂)₂Substituted with one or two groups;

r' independently represents hydrogen, halogen, C1-C8 alkoxy, C1-C8 alkoxy C1-C8 alkyl, C1-C8 alkyl, C8-C8 alkenyl, C8-C8 alkynyl, C8-C8 cycloalkyl C8 alkyl, C8-C8 cycloalkenyl C8 alkyl, aryl C8-C8 alkyl, heterocyclyl or heterocyclyl C8-C8 alkyl, wherein "C8-C8 alkyl", "C8-C8 alkenyl" or "C8-C8 alkynyl" independently represents unsubstituted or substituted by halogen, and "C8-C8 cycloalkyl", "C8-C8 alkyl", "C8-C8 cycloalkenyl" or "C8-C8 cycloalkenyl" aryl 8 "8 alkyl, "aryl C1-C8 alkyl", "heterocyclyl" OR "heterocyclyl C1-C8 alkyl" are each independently unsubstituted OR substituted by a group selected from oxo, halogen, cyano, nitro, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, halogenated C1-C8 alkyl, halogenated C2-C8 alkenyl, halogenated C2-C8 alkynyl, halogenated C3-C8 cycloalkyl, C3-C8 cycloalkyl substituted by C1-C8 alkyl, -OR₁₄、-SR₁₄、-(CO)OR₁₄、-(SO₂)R₁₄、-N(R₁₄)₂OR-O- (C1-C8 alkyl) - (CO) OR₁₄Or two adjacent carbon atoms in the ring and-OCH which are unsubstituted or substituted by halogen₂CH₂-or-OCH₂O-forms a fused ring;

r' each independently represents C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkyl C1-C8 alkyl, C3-C8 cycloalkenyl, C3-C8 cycloalkenyl C1-C8 alkyl, aryl C1-C8 alkyl, aryl C2-C8 alkenyl, heterocyclyl C1-C8 alkyl, OR heterocyclyl C2-C8 alkenyl, wherein each of said "C1-C8 alkyl", "C2-C8 alkenyl", OR "C2-C8 alkynyl" is independently unsubstituted OR selected from halogen, cyano, tri C1-C8 alkylsilyl, -OR₁₃、-SR₁₃、-O(CO)R₁₃、-(CO)R₁₃、-(CO)OR₁₃OR-O (CO) OR₁₃(iii) said "C3-C8 cycloalkyl", "C3-C8 cycloalkyl C1-C8 alkyl", "C3-C8 cycloalkenyl", "C3-C8 cycloalkenyl C1-C8 alkyl", "aryl C1-C8 alkyl", "aryl C2-C8 alkenyl", "heterocyclyl C1-C8 alkyl" or "heterocyclyl C2-C8 alkenyl", each independently being unsubstituted or selected from oxo, halogen, cyano, nitro, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, halogenated C1-C8 alkyl, halogenated C2-C8 alkenyl, halogenated C2-C8 alkynyl, halogenated C3-C8 cycloalkyl, C3-C8 cycloalkyl substituted by C1-C8 alkyl, -OR.₁₄、-SR₁₄、-(CO)OR₁₄、-(SO₂)R₁₄、-N(R₁₄)₂OR-O- (C1-C8 alkyl) - (CO) OR₁₄Or two adjacent carbon atoms in the ring and-OCH which are unsubstituted or substituted by halogen₂CH₂-or-OCH₂O-forms a fused ring;

W₁represents O, S, NH or N- (C1-C8 alkyl);

W₃each independently represents hydrogen, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkenyl, heterocyclyl, aryl, heteroaryl, substituted heteroaryl, or substituted heteroaryl, Wherein each of said "C1-C8 alkyl", "C2-C8 alkenyl" or "C2-C8 alkynyl" is independently unsubstituted or selected from the group consisting of halogen, cyano, nitro, C3-C8 cycloalkyl, tri-C1-C8 alkylsilyl, C3-C8 cycloalkenyl, heterocyclyl, aryl, heteroaryl, and heteroaryl, Said "C3-C8 cycloalkyl", "C3-C8 cycloalkenyl", "heterocyclyl", or "aryl" substituted with at least one ofThe radicals "are each independently unsubstituted OR substituted by radicals selected from the group consisting of oxo, halogen, cyano, nitro, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, haloC 1-C8 alkyl, haloC 2-C8 alkenyl, haloC 2-C8 alkynyl, haloC 3-C8 cycloalkyl, C3-C8 cycloalkyl substituted by C1-C8 alkyl, -OR₁₄、-SR₁₄、-(CO)OR₁₄、-(SO₂)R₁₄、-N(R₁₄)₂OR-O- (C1-C8 alkyl) - (CO) OR₁₄Or two adjacent carbon atoms in the ring and-OCH which are unsubstituted or substituted by halogen₂CH₂-or-OCH₂O-forms a fused ring;

or N (W)₃)₂RepresentsWhich is unsubstituted or substituted by at least one group selected from oxo, C1-C8 alkyl or C1-C8 alkoxycarbonyl;

X₁₁each independently represents hydrogen, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkyl C1-C8 alkyl, C8-C8 cycloalkenyl, heterocyclyl C8-C8 alkyl, aryl, or aryl C8-C8 alkyl, wherein said "C8-C8 cycloalkyl", "C8-C8 cycloalkyl C8-C8 alkyl", "C8-C8 cycloalkenyl C8-C8 alkyl", "heterocyclyl C8-C8 alkyl", "aryl", or "aryl C8-C8 alkyl" are each independently unsubstituted or selected from oxo, halogen, cyano, nitro, C8-C8 alkyl, C8-C8 alkenyl, C8-C8 alkynyl, C3-C8 cycloalkyl, halo-C1-C8 alkyl, halo-C2-C8 alkenyl, halo-C2-C8 alkynyl, halo-C3-C8 cycloalkyl, C3-C8 cycloalkyl substituted by C1-C8 alkyl, -OR₁₄、-SR₁₄、-(CO)OR₁₄、-(SO₂)R₁₄、-N(R₁₄)₂OR-O- (C1-C8 alkyl) - (CO) OR₁₄Or two adjacent carbon atoms in the ring and-OCH which are unsubstituted or substituted by halogen₂CH₂-or-OCH₂O-forms a fused ring;

X₁₂each independently represents C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkyl C1-C8 alkyl, C8-C8 cycloalkenyl, heterocyclyl C8-C8 alkyl, aryl, or aryl C8-C8 alkyl, wherein said "C8-C8 cycloalkyl", "C8-C8 cycloalkyl C8-C8 alkyl", "C8-C8 cycloalkenyl C8-C8 alkyl", "heterocyclyl" C8-C8 alkyl "," aryl ", or" aryl C8-C8 alkyl "are each independently unsubstituted or selected from oxo, halogen, cyano, nitro, C8-C8 alkyl, C8-C8 alkenyl, C8-C8 alkynyl, C8-C8 alkynyl, C3-C8 cycloalkyl, halo-C1-C8 alkyl, halo-C2-C8 alkenyl, halo-C2-C8 alkynyl, halo-C3-C8 cycloalkyl, C3-C8 cycloalkyl substituted by C1-C8 alkyl, -OR₁₄、-SR₁₄、-(CO)OR₁₄、-(SO₂)R₁₄、-N(R₁₄)₂OR-O- (C1-C8 alkyl) - (CO) OR₁₄Or two adjacent carbon atoms in the ring and-OCH which are unsubstituted or substituted by halogen₂CH₂-or-OCH₂O-forms a fused ring;

X₁₃、X₁₄each independently represents hydrogen, halogen, cyano, C1-C8 alkoxy, C1-C8 alkoxy C1-C8 alkyl, C1-C8 alkylcarbonyl, C1-C8 alkoxycarbonyl, C1-C8 alkylsulfonyl, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkyl C1-C8 alkyl, C3-C8 cycloalkenyl, C3-C8 cycloalkenyl C1-C8 alkyl, aryl C1-C8 alkyl, heterocyclyl or heterocyclyl C1-C8 alkyl, or the group CX₁₃X₁₄Together form a 5-to 8-membered carbocyclic or oxygen, sulfur or nitrogen containing heterocyclic ring, or a group NX₁₃X₁₄Are formed togetherWherein each of said "C1-C8 alkyl", "C2-C8 alkenyl" or "C2-C8 alkynyl" is independently unsubstituted or substituted with halogen, and said "C3-C8 cycloalkyl", "C3-C8 cycloalkyl C1-C8 alkyl", "C3-C8 cycloalkenyl", "C3-C8 cycloalkenyl C1-C8 alkyl", "aryl C1-C8 alkyl", "heterocycle" is optionally substituted with halogenThe group "OR" heterocyclyl C1-C8 alkyl "is each independently unsubstituted OR substituted by a group selected from oxo, halogen, cyano, nitro, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, haloC 1-C8 alkyl, haloC 2-C8 alkenyl, haloC 2-C8 alkynyl, haloC 3-C8 cycloalkyl, C3-C8 cycloalkyl substituted with C1-C8 alkyl, -OR₁₄、-SR₁₄、-(CO)OR₁₄、-(SO₂)R₁₄、-N(R₁₄)₂OR-O- (C1-C8 alkyl) - (CO) OR₁₄Or two adjacent carbon atoms in the ring and-OCH which are unsubstituted or substituted by halogen₂CH₂-or-OCH₂O-forms a condensed ring, and the 5-to 8-membered carbocycle or heterocycle containing oxygen, sulfur or nitrogen is unsubstituted or substituted by at least one group selected from C1-C8 alkyl, C1-C8 alkoxycarbonyl or benzyl, or forms a condensed ring structure with aryl or heterocyclic group; the above-mentionedIs unsubstituted or substituted by at least one group selected from oxo, C1-C8 alkyl or C1-C8 alkoxycarbonyl;

R₁、R₂、R₆、R₁₀、R₁₇、R₁₈、R₂₂、R₂₅、R₃₂each independently represents hydrogen, cyano, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, formyl C1-C8 alkyl, cyano C1-C8 alkyl, amino C1-C8 alkyl, aminocarbonyl C1-C8 alkyl, aminosulfonyl, C3-C8 cycloalkyl, C3-C8 cycloalkyl C1-C8 alkyl, C3-C8 cycloalkenyl, C3-C8 cycloalkenyl C1-C8 alkyl, heterocyclyl C1-C8 alkyl, aryl C1-C8 alkyl, R8 alkyl₄R₅N-(CO)-NR₃-、R₃-S(O)_m- (C1-C8 alkyl)_n-、R₃-O- (C1-C8 alkyl)_n-、R₃- (CO) - (C1-C8 alkyl)_n-、R₃-O- (C1-C8 alkyl)_n-(CO)-、R₃-(CO)-O-(C1-C8 alkyl group)_n-、R₃-S- (CO) - (C1-C8 alkyl)_n-、R₃-O- (CO) - (C1-C8 alkyl) -or R₃-O- (CO) -O- (C1-C8 alkyl) -, wherein,

the "C1-C8 alkyl", "C2-C8 alkenyl" or "C2-C8 alkynyl" each independently is unsubstituted or substituted with halogen,

the "amino", "amino C1-C8 alkyl", "aminocarbonyl C1-C8 alkyl" or "aminosulfonyl" groups are each independently unsubstituted or selected from the group consisting of₁₁、-OR₁₁、-(CO)R₁₁、-(CO)OR₁₁- (C1-C8 alkyl) - (CO) OR₁₁、-(SO₂)R₁₁、-(SO₂)OR₁₁- (C1-C8 alkyl) - (SO)₂)R₁₁、-(CO)N(R₁₂)₂Or- (SO)₂)N(R₁₂)₂Substituted with one or two of the groups in (a),

the "C3-C8 cycloalkyl", "C3-C8 cycloalkyl C1-C8 alkyl", "C3-C8 cycloalkenyl", "C3-C8 cycloalkenyl C1-C8 alkyl", "heterocyclyl C1-C8 alkyl", "aryl" OR "aryl C1-C8 alkyl" are each independently unsubstituted OR selected from oxo, halogen, cyano, nitro, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, halo C1-C8 alkyl, halo C2-C8 alkenyl, halo C8-C8 alkynyl, halo C8-C8 cycloalkyl, C8-C8 cycloalkyl substituted by C8-C8 alkyl, -OR₁₄、-SR₁₄、-(CO)OR₁₄、-(SO₂)R₁₄、-N(R₁₄)₂OR-O- (C1-C8 alkyl) - (CO) OR₁₄Or two adjacent carbon atoms in the ring and-OCH which are unsubstituted or substituted by halogen₂CH₂-or-OCH₂O-forms a fused ring;

or R₁₇、R₁₈Together form-CH which is unsubstituted or substituted by at least one group selected from halogen, C1-C8 alkyl or haloC 1-C8 alkyl₂CH₂CH₂CH₂-or-CH₂CH₂OCH₂-；

R₃、R₄、R₅Each independently represents hydrogen, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkyl C1-C8 alkyl, C8-C8 cycloalkenyl, heterocyclyl C8-C8 alkyl, aryl or aryl C8-C8 alkyl, wherein said "C8-C8 alkyl", "C8-C8 alkenyl" or "C8-C8 alkynyl" are each independently unsubstituted or substituted by halogen and said "C8-C8 cycloalkyl", "C8-C8 cycloalkyl C8-C8 alkyl", "C8-C8 cycloalkenyl", "C8-C8 alkyl", "C8-C8 aryl" or "aryl is each independently unsubstituted or substituted by a halogen, Halogen, cyano, nitro, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, halogenated C1-C8 alkyl, halogenated C2-C8 alkenyl, halogenated C2-C8 alkynyl, halogenated C3-C8 cycloalkyl, C3-C8 cycloalkyl substituted by C1-C8 alkyl, -OR₁₄、-SR₁₄、-(CO)OR₁₄、-(SO₂)R₁₄、-N(R₁₄)₂OR-O- (C1-C8 alkyl) - (CO) OR₁₄Or two adjacent carbon atoms in the ring and-OCH which are unsubstituted or substituted by halogen₂CH₂-or-OCH₂O-forms a fused ring;

R₇、R₈、R₇ ^'、R₈ ^'、R₉、R₁₉、R₂₀、R₂₁、R₂₃、R₂₄、R₂₆、R₂₇、R₂₈、R₂₉、R₃₀、R₃₁、R₃₃、R₃₄、R₃₅、R₃₆、R₃₇、R₃₈、R₃₉、R₄₀、R₄₁、R₄₂、R₄₃、R₄₄、R₄₅、R₄₆、R₄₇、R₄₈、R₄₉、R₅₀、R₅₁each independently represents hydrogen, halogen, hydroxyl, sulfhydryl, formyl, hydroxyl C1-C8 alkyl, nitro, cyano, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 ringAlkyl, C3-C8 cycloalkyl C1-C8 alkyl, C3-C8 cycloalkenyl, C3-C8 cycloalkenyl C1-C8 alkyl, -OR₁₁、-SR₁₁、-(SO)R₁₁、-(SO₂)R₁₁、-(SO₂)OR₁₁、-O(SO₂)R₁₁、-N(R₁₂)₂Phenyl or benzyl, wherein,

said "C1-C8 alkyl", "C2-C8 alkenyl", "C2-C8 alkynyl", "C3-C8 cycloalkyl", "C3-C8 cycloalkyl C1-C8 alkyl", "C3-C8 cycloalkenyl" or "C3-C8 cycloalkenyl C1-C8 alkyl" each independently being unsubstituted or substituted by halogen, said "phenyl" or "benzyl" each independently being unsubstituted or substituted by at least one group selected from halogen, cyano, nitro, C1-C8 alkyl, halo C1-C8 alkyl, C1-C8 alkoxycarbonyl 1-C8 alkylthio, C1-C8 alkylsulfonyl, C1-C8 alkoxy or halo C1-C8 alkoxy;

or R₇、R₈Together form-CH which is unsubstituted or substituted by at least one group selected from halogen, C1-C8 alkyl or haloC 1-C8 alkyl₂CH₂CH₂CH₂-or-CH ═ CH-;

or R₁₉、R₂₀Together form-CH which is unsubstituted or substituted by at least one group selected from halogen, C1-C8 alkyl or haloC 1-C8 alkyl₂CH₂CH₂CH₂-or-CH₂CH＝CHCH₂-；

Or R₂₁、R₂₂Together form-CH which is unsubstituted or substituted by at least one group selected from halogen, C1-C8 alkyl or haloC 1-C8 alkyl₂CH₂CH₂-、-CH₂OCH₂CH₂-or-CH₂CH₂CH₂CH₂-；

R₁₁Each independently represents C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkyl C1-C8 alkyl, C3-C8 cycloalkenyl, C3-C8 cycloalkenyl C1-C8 alkyl, phenyl or benzyl, wherein each of said "C1-C8 alkyl", "C2-C8 alkenyl" or "C2-C8 alkynyl" independently is unsubstitutedOr substituted by halogen, said "phenyl" or "benzyl" each independently being unsubstituted or substituted by at least one group selected from halogen, cyano, nitro, C1-C8 alkyl, halo-C1-C8 alkyl, C1-C8 alkoxycarbonyl, C1-C8 alkylthio, C1-C8 alkylsulfonyl, C1-C8 alkoxy or halo-C1-C8 alkoxy;

R₁₂each independently represents hydrogen, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C1-C8 alkoxy, C1-C8 alkylsulfonyl, C3-C8 cycloalkyl, C3-C8 cycloalkyl C1-C8 alkyl, C3-C8 cycloalkenyl or C3-C8 cycloalkenyl C1-C8 alkyl, or- (CO) N (R) N₁₂)₂Or- (SO)₂)N(R₁₂)₂Group N (R) of (1)₁₂)₂Each independently represents Which is unsubstituted or substituted by at least one group selected from oxo, C1-C8 alkyl or C1-C8 alkoxycarbonyl;

R₁₃each independently represents C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, phenyl, or phenyl substituted by at least one group selected from: halogen, cyano, nitro, C1-C8 alkyl, halogenated C1-C8 alkyl, C1-C8 alkoxy, halogenated C1-C8 alkoxy, C1-C8 alkoxycarbonyl, C1-C8 alkylthio, C1-C8 alkylsulfonyl or phenoxy substituted by at least one group selected from halogen, cyano, nitro, C1-C8 alkyl, halogenated C1-C8 alkyl, C1-C8 alkoxy or halogenated C1-C8 alkoxy;

R₁₄each independently represents hydrogen, C1-C8 alkyl, halogenated C1-C8 alkyl, phenyl or phenyl substituted by at least one group selected from halogen, cyano, nitro, C1-C8 alkyl, halogenated C1-C8 alkyl, C1-C8 alkoxycarbonyl, C1-C8 alkylthio, C1-C8 alkylsulfonyl, C1-C8 alkoxy or halogenated C1-C8 alkoxy;

R₁₅、R₁₆、R₅₂each independently represents hydrogen, halogen, C1-C8 alkaneA group, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkyl C1-C8 alkyl, C3-C8 cycloalkenyl or C3-C8 cycloalkenyl C1-C8 alkyl, wherein said "C1-C8 alkyl", "C2-C8 alkenyl", "C2-C8 alkynyl", "C3-C8 cycloalkyl", "C3-C8 cycloalkyl C1-C8 alkyl", "C3-C8 cycloalkenyl" or "C3-C8 cycloalkenyl C1-C8 alkyl" are each independently unsubstituted or substituted by halogen.

More preferably, Y represents halogen, halogeno-C1-C6 alkyl, cyano, nitro or amino;

het represents a cyclic structure sharing two carbon atoms at 4-and 5-positions with the isoxazoline ring to form a fused ring, the cyclic structure being a 3-to 8-membered saturated or unsaturated carbocyclic ring or containing a group selected from O, S, N, NH, CO, SO₂Or C ═ N-O-R₁₄In which 1,2 or 3 hetero atoms in the saturated or unsaturated heterocyclic ring, except for the 4-and 5-positions, respectively, are replaced by X₂Or X₁Independently of the substitution, the other positions on the Het are each unsubstituted OR substituted by a group selected from halogen, cyano, nitro, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, haloC 1-C6 alkyl, haloC 2-C6 alkenyl, haloC 2-C6 alkynyl, haloC 3-C6 cycloalkyl, C3-C6 cycloalkyl substituted by C1-C6 alkyl, -OR₁₄、-SR₁₄、-SOR₁₄、-(CO)OR₁₄、-(SO₂)R₁₄、-N(R₁₄)₂OR-O- (CO) OR₁₄Is substituted with at least one radical group;

X₁、X₂each independently represents hydrogen, halogen, nitro, cyano, thiocyanato, hydroxyl, mercapto, sulfonic acid, formyl, haloformyl, azido, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C6 alkyl, C3-C6 cycloalkenyl, C3-C6 cycloalkenyl C1-C6 alkyl, -PO (OR')₂、-OR”、-(CO)R”、-SR”、-(SO)R”、-(SO₂)R”、-Si(R”)₃、-O(CO)R”、-O-(SO₂)R”、-S(CO)R”、-(SO₂)OR”、-O(CO)OR”、-(CO)(CO)OR”、-CR’＝N-OH, -CR '═ N-O-R', heterocyclyl C1-C6 alkyl, aryl C1-C6 alkyl, amino C1-C6 alkyl, aminocarbonyl C1-C6 alkyl, aminocarbonyloxy C1-C6 alkyl, aminothiocarbonyloxy C1-C6 alkyl, aminosulfonyl or aminosulfonyloxy C1-C6 alkyl, where,

said "C1-C6 alkyl", "C2-C6 alkenyl" OR "C2-C6 alkynyl" are each independently unsubstituted OR substituted with a substituent selected from the group consisting of halogen, cyano, hydroxy, mercapto, carboxyl, -OR ", (CO) R", (SR) ", - (SO)₂)R”、-O(CO)H、-O(CO)R”、-O-(SO₂) R ", - (CO) OR", -O (CO) OH, — O (CO) OR ", -O- (C1-C6 alkyl) - (CO) OH OR-O- (C1-C6 alkyl) - (CO) OR",

the "C3-C6 cycloalkyl", "C3-C6 cycloalkyl C1-C6 alkyl", "C3-C6 cycloalkenyl", "C3-C6 cycloalkenyl C1-C6 alkyl", "heterocyclyl C1-C6 alkyl", "aryl" OR "aryl C1-C6 alkyl" are each independently unsubstituted OR selected from oxo, halogen, cyano, nitro, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, halo C1-C6 alkyl, halo C2-C6 alkenyl, halo C6-C6 alkynyl, halo C6-C6 cycloalkyl, C6-C6 cycloalkyl substituted by C6-C6 alkyl, -OR₁₄、-SR₁₄、-(CO)OR₁₄、-(SO₂)R₁₄、-N(R₁₄)₂OR-O- (C1-C6 alkyl) - (CO) OR₁₄Or two adjacent carbon atoms in the ring and-OCH which are unsubstituted or substituted by halogen₂CH₂-or-OCH₂O-forms a condensed ring,

the "amino", "amino C1-C6 alkyl", "aminocarbonyl C1-C6 alkyl", "aminocarbonyloxy C1-C6 alkyl", "aminothiocarbonyloxy C1-C6 alkyl", "aminosulfonyl" or "aminosulfonyloxy C1-C6 alkyl" are each independently unsubstituted or selected from the group consisting of₁₁、-OR₁₁、-(CO)R₁₁、-(CO)OR₁₁- (C1-C6 alkyl) - (CO) OR₁₁、-(SO₂)R₁₁、-(SO₂)OR₁₁- (C1-C6 alkyl) - (SO)₂)R₁₁、-(CO)N(R₁₂)₂Or- (SO)₂)N(R₁₂)₂Substituted with one or two groups;

r' independently represents hydrogen, halogen, C1-C6 alkoxy, C1-C6 alkoxy C1-C6 alkyl, C1-C6 alkyl, C6-C6 alkenyl, C6-C6 alkynyl, C6-C6 cycloalkyl C6 alkyl, C6-C6 cycloalkenyl C6 alkyl, aryl C6-C6 alkyl, heterocyclyl or heterocyclyl C6-C6 alkyl, wherein "C6-C6 alkyl", "C6-C6 alkenyl" or "C6-C6 alkynyl" independently represents unsubstituted or substituted by halogen, and "C6-C6 cycloalkyl", "C6-C6 alkyl", "C6-C6 cycloalkenyl" or "C6-C6 cycloalkenyl" aryl 6 "6 alkyl, "aryl C1-C6 alkyl", "heterocyclyl" OR "heterocyclyl C1-C6 alkyl" are each independently unsubstituted OR substituted by a group selected from oxo, halogen, cyano, nitro, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, halogenated C1-C6 alkyl, halogenated C2-C6 alkenyl, halogenated C2-C6 alkynyl, halogenated C3-C6 cycloalkyl, C3-C6 cycloalkyl substituted by C1-C6 alkyl, -OR₁₄、-SR₁₄、-(CO)OR₁₄、-(SO₂)R₁₄、-N(R₁₄)₂OR-O- (C1-C6 alkyl) - (CO) OR₁₄Or two adjacent carbon atoms in the ring and-OCH which are unsubstituted or substituted by halogen₂CH₂-or-OCH₂O-forms a fused ring;

r' each independently represents C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C6 alkyl, C3-C6 cycloalkenyl, C3-C6 cycloalkenyl C1-C6 alkyl, aryl C1-C6 alkyl, aryl C2-C6 alkenyl, heterocyclyl C1-C6 alkyl, OR heterocyclyl C2-C6 alkenyl, wherein each of said "C1-C6 alkyl", "C2-C6 alkenyl", OR "C2-C6 alkynyl" is independently unsubstituted OR selected from halogen, cyano, tri C1-C6 alkylsilyl, -OR₁₃、-SR₁₃、-O(CO)R₁₃、-(CO)R₁₃、-(CO)OR₁₃OR-O (CO) OR₁₃Substituted by 1,2 or 3 groups ofSaid "C3-C6 cycloalkyl", "C3-C6 cycloalkyl C1-C6 alkyl", "C3-C6 cycloalkenyl", "C3-C6 cycloalkenyl C1-C6 alkyl", "aryl C1-C6 alkyl", "aryl C2-C6 alkenyl", "heterocyclyl C1-C6 alkyl" OR "heterocyclyl C2-C6 alkenyl" are each independently unsubstituted OR selected from oxo, halogen, cyano, nitro, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, halogenated C1-C6 alkyl, halogenated C2-C6 alkenyl, halogenated C2-C6 alkynyl, halogenated C3-C6 cycloalkyl, C3-C6 cycloalkyl substituted with C1-C6 alkyl, -OR₁₄、-SR₁₄、-(CO)OR₁₄、-(SO₂)R₁₄、-N(R₁₄)₂OR-O- (C1-C6 alkyl) - (CO) OR₁₄Or two adjacent carbon atoms in the ring and-OCH which are unsubstituted or substituted by halogen₂CH₂-or-OCH₂O-forms a fused ring;

W₁represents O, S, NH or N- (C1-C6 alkyl);

W₃each independently represents hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkenyl, heterocyclyl, aryl, heteroaryl, substituted heteroaryl, or substituted heteroaryl, Wherein each of said "C1-C6 alkyl", "C2-C6 alkenyl" or "C2-C6 alkynyl" is independently unsubstituted or selected from the group consisting of halogen, cyano, nitro, C3-C6 cycloalkyl, tri-C1-C6 alkylsilyl, C3-C6 cycloalkenyl, heterocyclyl, aryl, heteroaryl, is substituted with 1,2 or 3 of the groups "C3-C6 cycloalkyl", "C3-C6 cycloalkenyl", "heterocyclyl" or "aryl", each independently is unsubstituted or selected fromOxo, halogen, cyano, nitro, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, halogenated C1-C6 alkyl, halogenated C2-C6 alkenyl, halogenated C2-C6 alkynyl, halogenated C3-C6 cycloalkyl, C3-C6 cycloalkyl substituted by C1-C6 alkyl, -OR₁₄、-SR₁₄、-(CO)OR₁₄、-(SO₂)R₁₄、-N(R₁₄)₂OR-O- (C1-C6 alkyl) - (CO) OR₁₄Or two adjacent carbon atoms in the ring and-OCH which are unsubstituted or substituted by halogen₂CH₂-or-OCH₂O-forms a fused ring;

or N (W)₃)₂RepresentsWhich is unsubstituted or substituted by 1,2 or 3 groups selected from oxo, C1-C6 alkyl or C1-C6 alkoxycarbonyl;

X₁₁each independently represents hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C6 alkyl, C6-C6 cycloalkenyl, heterocyclyl C6-C6 alkyl, aryl, or aryl C6-C6 alkyl, wherein said "C6-C6 cycloalkyl", "C6-C6 cycloalkyl C6-C6 alkyl", "C6-C6 cycloalkenyl C6-C6 alkyl", "heterocyclyl C6-C6 alkyl", "aryl", or "aryl C6-C6 alkyl" are each independently unsubstituted or selected from oxo, halogen, cyano, nitro, C6-C6 alkyl, C6-C6 alkenyl, C6-C6 alkynyl, C3-C6 cycloalkyl, halo-C1-C6 alkyl, halo-C2-C6 alkenyl, halo-C2-C6 alkynyl, halo-C3-C6 cycloalkyl, C3-C6 cycloalkyl substituted by C1-C6 alkyl, -OR₁₄、-SR₁₄、-(CO)OR₁₄、-(SO₂)R₁₄、-N(R₁₄)₂OR-O- (C1-C6 alkyl) - (CO) OR₁₄Or two adjacent carbon atoms in the ring and-OCH which are unsubstituted or substituted by halogen₂CH₂-or-OCH₂O-forms a fused ring;

X₁₂each independently represents a C1-C6 alkyl group,C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl C6-C6 alkyl, C6-C6 cycloalkenyl C6-C6 alkyl, heterocyclyl C6-C6 alkyl, aryl or aryl C6-C6 alkyl, wherein said "C6-C6 cycloalkyl", "C6-C6 cycloalkyl C6-C6 alkyl", "C6-C6 cycloalkenyl", cycloalkenyl C6-C6 alkyl "," heterocyclyl C6-C6 alkyl "," aryl "or" aryl C6-C6 alkyl "are each independently unsubstituted or selected from oxo, halogen, cyano, nitro, C6-C6 alkyl, C6-C6 alkenyl, C6-C6 alkynyl, C6-C6 alkyl halide, C6-C6 alkyl, C6 alkyl, Halogenated C2-C6 alkenyl, halogenated C2-C6 alkynyl, halogenated C3-C6 cycloalkyl, C3-C6 cycloalkyl substituted by C1-C6 alkyl, -OR₁₄、-SR₁₄、-(CO)OR₁₄、-(SO₂)R₁₄、-N(R₁₄)₂OR-O- (C1-C6 alkyl) - (CO) OR₁₄Or two adjacent carbon atoms in the ring and-OCH which are unsubstituted or substituted by halogen₂CH₂-or-OCH₂O-forms a fused ring;

X₁₃、X₁₄each independently represents hydrogen, halogen, cyano, C1-C6 alkoxy, C1-C6 alkoxy C1-C6 alkyl, C1-C6 alkylcarbonyl, C1-C6 alkoxycarbonyl, C1-C6 alkylsulfonyl, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C6 alkyl, C3-C6 cycloalkenyl, C3-C6 cycloalkenyl C1-C6 alkyl, aryl C1-C6 alkyl, heterocyclyl or heterocyclyl C1-C6 alkyl, or the group CX₁₃X₁₄Together form a 5-to 8-membered saturated carbocyclic ring,Or a group NX₁₃X₁₄Are formed togetherWherein each of said "C1-C6 alkyl", "C2-C6 alkenyl" or "C2-C6 alkynyl" is independently unsubstituted or substituted with halogen, and said "C3-C6 cycloalkyl", "C3-C6 cycloalkyl C1-C6 alkyl", "C3-C6 cycloalkenyl", "C3-C6 cycloalkenyl C1-C6 alkaneThe group "," aryl C1-C6 alkyl "," heterocyclyl "OR" heterocyclyl C1-C6 alkyl "are each independently unsubstituted OR selected from oxo, halogen, cyano, nitro, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, halogenated C1-C6 alkyl, halogenated C2-C6 alkenyl, halogenated C2-C6 alkynyl, halogenated C3-C6 cycloalkyl, C3-C6 cycloalkyl substituted with C1-C6 alkyl, -OR₁₄、-SR₁₄、-(CO)OR₁₄、-(SO₂)R₁₄、-N(R₁₄)₂OR-O- (C1-C6 alkyl) - (CO) OR₁₄Or two adjacent carbon atoms in the ring and-OCH which are unsubstituted or substituted by halogen₂CH₂-or-OCH₂O-forms a condensed ring, the "5-to 8-membered saturated carbocyclic ring"is unsubstituted or substituted by 1,2 or 3 groups selected from C1-C6 alkyl, C1-C6 alkoxycarbonyl or benzyl, or forms a fused ring structure with an aryl or heterocyclic groupIs unsubstituted or substituted by 1,2 or 3 groups selected from oxo, C1-C6 alkyl or C1-C6 alkoxycarbonyl;

R₁、R₂、R₆、R₁₀、R₁₇、R₁₈、R₂₂、R₂₅、R₃₂each independently represents hydrogen, cyano, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, formyl C1-C6 alkyl, cyano C1-C6 alkyl, amino C1-C6 alkyl, aminocarbonyl C1-C6 alkyl, aminosulfonyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C6 alkyl, C3-C6 cycloalkenyl, C3-C6 cycloalkenyl C1-C6 alkyl, heterocyclyl C1-C6 alkyl, aryl C1-C6 alkyl, R6 alkyl₄R₅N-(CO)-NR₃-、R₃-S(O)_m- (C1-C6 alkyl)_n-、R₃-O- (C1-C6 alkyl)_n-、R₃- (CO) - (C1-C6 alkyl)_n-、R₃-O- (C1-C6 alkyl)_n-(CO)-、R₃- (CO) -O- (C1-C6 alkyl)_n-、R₃-S- (CO) - (C1-C6 alkyl)_n-、R₃-O- (CO) - (C1-C6 alkyl) -or R₃-O- (CO) -O- (C1-C6 alkyl) -, wherein,

the "C1-C6 alkyl", "C2-C6 alkenyl" or "C2-C6 alkynyl" each independently is unsubstituted or substituted with halogen,

the "amino", "amino C1-C6 alkyl", "aminocarbonyl C1-C6 alkyl" or "aminosulfonyl" groups are each independently unsubstituted or selected from the group consisting of₁₁、-OR₁₁、-(CO)R₁₁、-(CO)OR₁₁- (C1-C6 alkyl) - (CO) OR₁₁、-(SO₂)R₁₁、-(SO₂)OR₁₁- (C1-C6 alkyl) - (SO)₂)R₁₁、-(CO)N(R₁₂)₂Or- (SO)₂)N(R₁₂)₂Substituted with one or two of the groups in (a),

the "C3-C6 cycloalkyl", "C3-C6 cycloalkyl C1-C6 alkyl", "C3-C6 cycloalkenyl", "C3-C6 cycloalkenyl C1-C6 alkyl", "heterocyclyl C1-C6 alkyl", "aryl" OR "aryl C1-C6 alkyl" are each independently unsubstituted OR selected from oxo, halogen, cyano, nitro, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, halo C1-C6 alkyl, halo C2-C6 alkenyl, halo C6-C6 alkynyl, halo C6-C6 cycloalkyl, C6-C6 cycloalkyl substituted by C6-C6 alkyl, -OR₁₄、-SR₁₄、-(CO)OR₁₄、-(SO₂)R₁₄、-N(R₁₄)₂OR-O- (C1-C6 alkyl) - (CO) OR₁₄Or two adjacent carbon atoms in the ring and-OCH which are unsubstituted or substituted by halogen₂CH₂-or-OCH₂O-forms a fused ring;

or R₁₇、R₁₈Together form at least one unsubstituted or substituted halogen, C1-C6 alkyl or halogenated C1-C6 alkyl groupof-CH substituted by radicals₂CH₂CH₂CH₂-or-CH₂CH₂OCH₂-；

R₃、R₄、R₅Each independently represents hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C6 alkyl, C6-C6 cycloalkenyl, heterocyclyl C6-C6 alkyl, aryl or aryl C6-C6 alkyl, wherein said "C6-C6 alkyl", "C6-C6 alkenyl" or "C6-C6 alkynyl" are each independently unsubstituted or substituted by halogen and said "C6-C6 cycloalkyl", "C6-C6 cycloalkyl C6-C6 alkyl", "C6-C6 cycloalkenyl", "C6-C6 alkyl", "C6-C6 aryl" or "aryl is each independently unsubstituted or substituted by a halogen, Halogen, cyano, nitro, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, halogenated C1-C6 alkyl, halogenated C2-C6 alkenyl, halogenated C2-C6 alkynyl, halogenated C3-C6 cycloalkyl, C3-C6 cycloalkyl substituted by C1-C6 alkyl, -OR₁₄、-SR₁₄、-(CO)OR₁₄、-(SO₂)R₁₄、-N(R₁₄)₂OR-O- (C1-C6 alkyl) - (CO) OR₁₄Or two adjacent carbon atoms in the ring and-OCH which are unsubstituted or substituted by halogen₂CH₂-or-OCH₂O-forms a fused ring;

R₇、R₈、R₇’、R₈’、R₉、R₁₉、R₂₀、R₂₁、R₂₃、R₂₄、R₂₆、R₂₇、R₂₈、R₂₉、R₃₀、R₃₁、R₃₃、R₃₄、R₃₅、R₃₆、R₃₇、R₃₈、R₃₉、R₄₀、R₄₁、R₄₂、R₄₃、R₄₄、R₄₅、R₄₆、R₄₇、R₄₈、R₄₉、R₅₀、R₅₁each independently represents hydrogen, halogen, hydroxy, mercapto, or methylAcyl, hydroxyl C1-C6 alkyl, nitro, cyano, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C6 alkyl, C3-C6 cycloalkenyl, C3-C6 cycloalkenyl C1-C6 alkyl, -OR₁₁、-SR₁₁、-(SO)R₁₁、-(SO₂)R₁₁、-(SO₂)OR₁₁、-O(SO₂)R₁₁、-N(R₁₂)₂Phenyl or benzyl, wherein,

said "C1-C6 alkyl", "C2-C6 alkenyl", "C2-C6 alkynyl", "C3-C6 cycloalkyl", "C3-C6 cycloalkyl C1-C6 alkyl", "C3-C6 cycloalkenyl" or "C3-C6 cycloalkenyl C1-C6 alkyl" each independently being unsubstituted or substituted by halogen, said "phenyl" or "benzyl" each independently being unsubstituted or substituted by at least one group selected from halogen, cyano, nitro, C1-C6 alkyl, halo C1-C6 alkyl, C1-C6 alkoxycarbonyl 1-C6 alkylthio, C1-C6 alkylsulfonyl, C1-C6 alkoxy or halo C1-C6 alkoxy;

or R₇、R₈Together form-CH which is unsubstituted or substituted by at least one group selected from halogen, C1-C6 alkyl or haloC 1-C6 alkyl₂CH₂CH₂CH₂-or-CH ═ CH-;

or R₁₉、R₂₀Together form-CH which is unsubstituted or substituted by at least one group selected from halogen, C1-C6 alkyl or haloC 1-C6 alkyl₂CH₂CH₂CH₂-or-CH₂CH＝CHCH₂-；

Or R₂₁、R₂₂Together form-CH which is unsubstituted or substituted by at least one group selected from halogen, C1-C6 alkyl or haloC 1-C6 alkyl₂CH₂CH₂-、-CH₂OCH₂CH₂-or-CH₂CH₂CH₂CH₂-；

R₁₁Each independently represents C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C6 alkyl, C3-C6 cycloalkenyl, C3-C6 cycloalkenyl C1-C6 alkyl, phenyl or benzyl,wherein "C1-C6 alkyl", "C2-C6 alkenyl" or "C2-C6 alkynyl" are each independently unsubstituted or substituted with halogen, and "phenyl" or "benzyl" are each independently unsubstituted or substituted with 1,2 or 3 groups selected from halogen, cyano, nitro, C1-C6 alkyl, halo C1-C6 alkyl, C1-C6 alkoxycarbonyl, C1-C6 alkylthio, C1-C6 alkylsulfonyl, C1-C6 alkoxy or halo C1-C6 alkoxy;

R₁₂each independently represents hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 alkoxy, C1-C6 alkylsulfonyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C6 alkyl, C3-C6 cycloalkenyl or C3-C6 cycloalkenyl C1-C6 alkyl, or- (CO) N (R) N₁₂)₂Or- (SO)₂)N(R₁₂)₂Group N (R) of (1)₁₂)₂Each independently represents Which is unsubstituted or substituted by 1,2 or 3 groups selected from oxo, C1-C6 alkyl or C1-C6 alkoxycarbonyl;

R₁₃each independently represents C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, phenyl or phenyl substituted by 1,2 or 3 groups selected from: halogen, cyano, nitro, C1-C6 alkyl, halogenated C1-C6 alkyl, C1-C6 alkoxy, halogenated C1-C6 alkoxy, C1-C6 alkoxycarbonyl, C1-C6 alkylthio, C1-C6 alkylsulfonyl or phenoxy substituted by 1,2 or 3 groups selected from halogen, cyano, nitro, C1-C6 alkyl, halogenated C1-C6 alkyl, C1-C6 alkoxy or halogenated C1-C6 alkoxy;

R₁₄each independently represents hydrogen, C1-C6 alkyl, halogenated C1-C6 alkyl, phenyl or phenyl substituted by 1,2 or 3 groups selected from halogen, cyano, nitro, C1-C6 alkyl, halogenated C1-C6 alkyl, C1-C6 alkoxycarbonyl, C1-C6 alkylthio, C1-C6 alkylsulfonyl, C1-C6 alkoxy or halogenated C1-C6 alkoxy;

R₁₅、R₁₆、R₅₂each independently represents hydrogen, halogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C6 alkyl, C3-C6 cycloalkenyl, or C3-C6 cycloalkenyl C1-C6 alkyl, wherein said "C1-C6 alkyl", "C2-C6 alkenyl", "C2-C6 alkynyl", "C3-C6 cycloalkyl", "C3-C6 cycloalkyl C1-C6 alkyl", "C3-C6 cycloalkenyl", or "C3-C6 cycloalkenyl C1-C6 alkyl" are each independently unsubstituted or substituted by halogen.

Further preferably, X₁、X₂Each independently represents hydrogen, halogen, nitro, cyano, thiocyanato, hydroxyl, mercapto, sulfonic acid, formyl, haloformyl, azido, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C3 alkyl, C3-C6 cycloalkenyl, C3-C6 cycloalkenyl C1-C3 alkyl, -PO (OR')₂、-OR”、-(CO)R”、-SR”、-(SO)R”、-(SO₂)R”、-Si(R”)₃、-O(CO)R”、-O-(SO₂)R”、-S(CO)R”、-(SO₂)OR”、-O(CO)OR”、-(CO)(CO)OR”、-CR '═ N-OH, -CR' ═ N-O-R ", heterocyclyl C1-C3 alkyl, aryl C1-C3 alkyl, amino C1-C3 alkyl, aminocarbonyl C1-C3 alkyl, aminocarbonyloxy C1-C3 alkyl, aminothiocarbonyloxy C1-C3 alkyl, aminosulfonyl or aminosulfonyloxy C1-C3 alkyl, where,

said "C1-C6 alkyl", "C2-C6 alkenyl" OR "C2-C6 alkynyl" are each independently unsubstituted OR substituted with a substituent selected from the group consisting of halogen, cyano, hydroxy, mercapto, carboxyl, -OR ", (CO) R", (SR) ", - (SO)₂)R”、-O(CO)H、-O(CO)R”、-O-(SO₂) R ", - (CO) OR", -O (CO) OH, — O (CO) OR ", -O- (C1-C3 alkyl) - (CO) OH OR-O- (C1-C3 alkyl) - (CO) OR",

the "C3-C6 cycloalkyl", "C3-C6 cycloalkyl C1-C3 alkyl", "C3-C6 cycloalkenyl", "C3-C6 cycloalkenyl C1-C3 alkyl, heterocyclyl C1-C3 alkyl, aryl, OR arylC 1-C3 alkyl are each independently unsubstituted OR selected from oxo, halogen, cyano, nitro, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, haloC 1-C6 alkyl, haloC 2-C6 alkenyl, haloC 2-C6 alkynyl, haloC 3-C6 cycloalkyl, C3-C6 cycloalkyl substituted with C1-C6 alkyl, -OR₁₄、-SR₁₄、-(CO)OR₁₄、-(SO₂)R₁₄、-N(R₁₄)₂OR-O- (C1-C3 alkyl) - (CO) OR₁₄Or two adjacent carbon atoms in the ring and-OCH which are unsubstituted or substituted by halogen₂CH₂-or-OCH₂O-forms a condensed ring,

the "amino", "amino C1-C3 alkyl", "aminocarbonyl C1-C3 alkyl", "aminocarbonyloxy C1-C3 alkyl", "aminothiocarbonyloxy C1-C3 alkyl", "aminosulfonyl" or "aminosulfonyloxy C1-C3 alkyl" are each independently unsubstituted or selected from the group consisting of₁₁、-OR₁₁、-(CO)R₁₁、-(CO)OR₁₁- (C1-C3 alkyl) - (CO) OR₁₁、-(SO₂)R₁₁、-(SO₂)OR₁₁- (C1-C3 alkyl) - (SO)₂)R₁₁、-(CO)N(R₁₂)₂Or- (SO)₂)N(R₁₂)₂Substituted with one or two groups;

r' independently represents hydrogen, halogen, C1-C6 alkoxy, C1-C6 alkoxy C1-C3 alkyl, C1-C6 alkyl, C6-C6 alkenyl, C6-C6 alkynyl, C6-C6 cycloalkyl C6 alkyl, C6-C6 cycloalkenyl C6 alkyl, aryl C6-C6 alkyl, heterocyclyl or heterocyclyl C6-C6 alkyl, wherein "C6-C6 alkyl", "C6-C6 alkenyl" or "C6-C6 alkynyl" independently represents unsubstituted or substituted by halogen, and "C6-C6 cycloalkyl", "C6-C6 alkyl", "C6-C6 cycloalkenyl" or "C6-C6 cycloalkenyl" aryl 6 "6 alkyl, The "aryl C1-C3 alkyl", "heterocyclyl" or "heterocyclyl C1-C3 alkyl" each independently is unsubstituted or selectedFrom oxo, halogen, cyano, nitro, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, halogenated C1-C6 alkyl, halogenated C2-C6 alkenyl, halogenated C2-C6 alkynyl, halogenated C3-C6 cycloalkyl, C3-C6 cycloalkyl substituted by C1-C6 alkyl, -OR₁₄、-SR₁₄、-(CO)OR₁₄、-(SO₂)R₁₄、-N(R₁₄)₂OR-O- (C1-C3 alkyl) - (CO) OR₁₄Or two adjacent carbon atoms in the ring and-OCH which are unsubstituted or substituted by halogen₂CH₂-or-OCH₂O-forms a fused ring;

r' each independently represents C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C3 alkyl, C3-C6 cycloalkenyl, C3-C6 cycloalkenyl C1-C3 alkyl, aryl C1-C3 alkyl, aryl C2-C3 alkenyl, heterocyclyl C1-C3 alkyl, OR heterocyclyl C2-C3 alkenyl, wherein each of said "C1-C6 alkyl", "C2-C6 alkenyl", OR "C2-C6 alkynyl" is independently unsubstituted OR selected from halogen, cyano, tri C1-C6 alkylsilyl, -OR₁₃、-SR₁₃、-O(CO)R₁₃、-(CO)R₁₃、-(CO)OR₁₃OR-O (CO) OR₁₃Said "C3-C6 cycloalkyl", "C3-C6 cycloalkyl C1-C3 alkyl", "C3-C6 cycloalkenyl", "C3-C6 cycloalkenyl C1-C3 alkyl", "aryl C1-C3 alkyl", "aryl C2-C3 alkenyl", "heterocyclyl C1-C3 alkyl" or "heterocyclyl C2-C3 alkenyl" each independently being unsubstituted or selected from oxo, halogen, cyano, nitro, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, halogenated C1-C6 alkyl, halogenated C2-C6 alkenyl, halogenated C2-C6 alkynyl, halogenated C3-C6 cycloalkyl, C3-C6 cycloalkyl substituted by C1-C6 alkyl, -OR.₁₄、-SR₁₄、-(CO)OR₁₄、-(SO₂)R₁₄、-N(R₁₄)₂OR-O- (C1-C3 alkyl) - (CO) OR₁₄Or two adjacent carbon atoms in the ring and-OCH which are unsubstituted or substituted by halogen₂CH₂-or-OCH₂O-forming condensed rings；

W₃Each independently represents hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkenyl, heterocyclyl, aryl, heteroaryl, substituted heteroaryl, or substituted heteroaryl, Wherein each of said "C1-C6 alkyl", "C2-C6 alkenyl" or "C2-C6 alkynyl" is independently unsubstituted or selected from the group consisting of halogen, cyano, nitro, C3-C6 cycloalkyl, tri-C1-C6 alkylsilyl, C3-C6 cycloalkenyl, heterocyclyl, aryl, heteroaryl, and heteroaryl, (ii) said "C3-C6 cycloalkyl", "C3-C6 cycloalkenyl", "heterocyclyl" OR "aryl" each independently being unsubstituted OR selected from oxo, halogen, cyano, nitro, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, halogenated C1-C6 alkyl, halogenated C2-C6 alkenyl, halogenated C2-C6 alkynyl, halogenated C3-C6 cycloalkyl, C3-C6 cycloalkyl substituted with C1-C6 alkyl, -OR₁₄、-SR₁₄、-(CO)OR₁₄、-(SO₂)R₁₄、-N(R₁₄)₂OR-O- (C1-C3 alkyl) - (CO) OR₁₄Or two adjacent carbon atoms in the ring and-OCH which are unsubstituted or substituted by halogen₂CH₂-or-OCH₂O-forms a fused ring;

or N (W)₃)₂RepresentsWhich is unsubstituted or substituted by 1,2 or 3 groups selected from oxo, C1-C6 alkyl or C1-C6 alkoxycarbonyl;

X₁₁each independently represents hydrogenC1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C6-C6 cycloalkyl C6-C6 alkyl, C6-C6 cycloalkenyl, heterocyclyl C6-C6 alkyl, aryl, or aryl C6-C6 alkyl, wherein each of said "C6-C6 cycloalkyl", "C6-C6 cycloalkyl C6 alkyl", "C6-C6 cycloalkenyl C6-C6 alkyl", "heterocyclyl C6-C6 alkyl", "aryl", or "aryl C6-C6 alkyl" is independently unsubstituted or selected from oxo, halogen, cyano, nitro, C6-C6 alkyl, C6-C6 alkenyl, C6-C6 cycloalkyl, C6-C6 alkynyl, Halogenated C1-C6 alkyl, halogenated C2-C6 alkenyl, halogenated C2-C6 alkynyl, halogenated C3-C6 cycloalkyl, C3-C6 cycloalkyl substituted by C1-C6 alkyl, -OR₁₄、-SR₁₄、-(CO)OR₁₄、-(SO₂)R₁₄、-N(R₁₄)₂OR-O- (C1-C3 alkyl) - (CO) OR₁₄Or two adjacent carbon atoms in the ring and-OCH which are unsubstituted or substituted by halogen₂CH₂-or-OCH₂O-forms a fused ring;

X₁₂each independently represents C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C3 alkyl, C3-C3 cycloalkenyl, heterocyclyl C3-C3 alkyl, aryl, or aryl C3-C3 alkyl, wherein said "C3-C3 cycloalkyl", "C3-C3 cycloalkyl C3-C3 alkyl", "C3-C3 cycloalkenyl C3-C3 alkyl", "heterocyclyl" C3-C3 alkyl "," aryl ", or" aryl C3-C3 alkyl "are each independently unsubstituted or selected from oxo, halogen, cyano, nitro, C3-C3 alkyl, C3-C3 alkenyl, C3-C3 alkynyl, C3-C3 alkynyl, C3-C6 cycloalkyl, halo-C1-C6 alkyl, halo-C2-C6 alkenyl, halo-C2-C6 alkynyl, halo-C3-C6 cycloalkyl, C3-C6 cycloalkyl substituted by C1-C6 alkyl, -OR₁₄、-SR₁₄、-(CO)OR₁₄、-(SO₂)R₁₄、-N(R₁₄)₂OR-O- (C1-C3 alkyl) - (CO) OR₁₄Or two adjacent carbon atoms in the ring and-OCH which are unsubstituted or substituted by halogen₂CH₂-or-OCH₂O-forms a fused ring;

X₁₃、X₁₄each independently represents hydrogen, halogen, cyano, C1-C6 alkoxy, C1-C6 alkoxy C1-C3 alkyl, C1-C6 alkylcarbonyl, C1-C6 alkoxycarbonyl, C1-C6 alkylsulfonyl, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C3 alkyl, C3-C6 cycloalkenyl, C3-C6 cycloalkenyl C1-C3 alkyl, aryl C1-C3 alkyl, heterocyclyl or heterocyclyl C1-C3 alkyl, or the group CX₁₃X₁₄Together form a 5-to 8-membered saturated carbocyclic ring,Or a group NX₁₃X₁₄Are formed togetherWherein each of said "C1-C6 alkyl", "C2-C6 alkenyl" or "C2-C6 alkynyl" is independently unsubstituted or substituted by halogen, and said "C3-C6 cycloalkyl", "C3-C6 cycloalkyl C1-C3 alkyl", "C3-C6 cycloalkenyl", "C3-C6 cycloalkenyl C6-C6 alkyl", "aryl C6-C6 alkyl", "heterocyclyl" or "heterocyclyl C6-C6 alkyl" is independently unsubstituted or substituted by an alkyl group selected from oxo, halogen, cyano, nitro, C6-C6 alkyl, C6-C6 alkenyl, C6-C6 alkynyl, C6-C6 cycloalkyl, haloC 6-C6 alkyl, haloC 6-C6 alkenyl, haloC 6-C6 alkynyl, haloC 6-C6 alkenyl, haloC 6-C6 cycloalkyl, C6-C6 cycloalkyl 6-C6 alkyl, C6 cycloalkyl 6-C6 alkyl, -OR₁₄、-SR₁₄、-(CO)OR₁₄、-(SO₂)R₁₄、-N(R₁₄)₂OR-O- (C1-C3 alkyl) - (CO) OR₁₄Or two adjacent carbon atoms in the ring and-OCH which are unsubstituted or substituted by halogen₂CH₂-or-OCH₂O-forms a condensed ring, the "5-to 8-membered saturated carbocyclic ring"is unsubstituted or 1,2 or 3 selected from C1-C6 alkyl, C1-C6 alkoxycarbonyl or benzylSubstituted by one group or forms a fused ring structure with phenyl or thienyl; the above-mentionedIs unsubstituted or substituted by 1,2 or 3 groups selected from oxo, C1-C6 alkyl or C1-C6 alkoxycarbonyl;

R₁₁each independently represents C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C3 alkyl, C3-C6 cycloalkenyl, C3-C6 cycloalkenyl C1-C3 alkyl, phenyl, benzyl, wherein the "C1-C6 alkyl", "C2-C6 alkenyl", or "C2-C6 alkynyl", respectively, are independently unsubstituted or substituted with halogen, said "phenyl" or "benzyl" are each independently unsubstituted or substituted with 1,2 or 3 groups selected from halogen, cyano, nitro, C1-C6 alkyl, halo C1-C6 alkyl, C1-C6 alkoxycarbonyl, C1-C6 alkylthio, C1-C6 alkylsulfonyl, C1-C6 alkoxy or halo C1-C6 alkoxy;

R₁₂each independently represents hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 alkoxy, C1-C6 alkylsulfonyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C3 alkyl, C3-C6 cycloalkenyl or C3-C6 cycloalkenyl C1-C3 alkyl, or- (CO) N (R) N₁₂)₂Or- (SO)₂)N(R₁₂)₂Group N (R) of (1)₁₂)₂Each independently represents Which is unsubstituted or substituted by 1,2 or 3 groups selected from oxo, C1-C6 alkyl or C1-C6 alkoxycarbonyl;

R₁₃each independently represents C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, phenyl or phenyl substituted by 1,2 or 3 groups selected from: halogen, cyano, nitro, C1-C6 alkyl, halo-C1-C6 alkyl, C1-C6 alkoxy, halo-C1-C6 alkoxy, C1-C6 alkoxycarbonyl, C1-C6 alkylthio, C1-C6 alkaneAlkylsulfonyl or phenoxy substituted by 1,2 or 3 groups selected from halogen, cyano, nitro, C1-C6 alkyl, halo-C1-C6 alkyl, C1-C6 alkoxy or halo-C1-C6 alkoxy;

R₁₄each independently represents hydrogen, C1-C6 alkyl, halogenated C1-C6 alkyl, phenyl or phenyl substituted by 1,2 or 3 groups selected from halogen, cyano, nitro, C1-C6 alkyl, halogenated C1-C6 alkyl, C1-C6 alkoxycarbonyl, C1-C6 alkylthio, C1-C6 alkylsulfonyl, C1-C6 alkoxy or halogenated C1-C6 alkoxy.

Still more preferably Het represents (wherein the bold portions correspond to the bold portions in the formula and the carbon atoms at both ends correspond to C4 and C5, respectively, without limitation, as long as Het is HetWhen is represented by the general formula) Except that the 4-and 5-positions in formula I are each independently replaced by X₂Or X₁Independently of the substitution, the other positions on the Het are each unsubstituted OR substituted by a group selected from halogen, cyano, nitro, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, haloC 1-C6 alkyl, haloC 2-C6 alkenyl, haloC 2-C6 alkynyl, haloC 3-C6 cycloalkyl, C3-C6 cycloalkyl substituted by C1-C6 alkyl, -OR₁₄、-SR₁₄、-SOR₁₄、-(CO)OR₁₄、-(SO₂)R₁₄、-N(R₁₄)₂OR-O- (C1-C3 alkyl) - (CO) OR₁₄1,2 or 3 groups of (a).

Still further preferably, Q represents

In the definition of the compounds of the above general formula and in all the formulae below, the terms used, whether used alone or in compound words, represent the following substituents: alkyl groups having more than two carbon atoms may be straight chain or branched. Such as the compound word "-alkyl- (CO) OR₁₁"the alkyl group may be-CH₂-、-CH₂CH₂-、-CH(CH₃)-、-C(CH₃)₂-and the like. Alkyl groups are, for example, C1 alkyl-methyl; c2 alkyl-ethyl; c3 alkyl-propyl such as n-propyl or isopropyl; c4 alkyl-butyl such as n-butyl, isobutyl, tert-butyl or 2-butyl; c5 alkyl-pentyl such as n-pentyl; c6 alkyl-hexyl radicals such as the n-hexyl, isohexyl and 1, 3-dimethylbutyl radical. Similarly, alkenyl is, for example, vinyl, allyl, 1-methylprop-2-en-1-yl, 2-methylprop-2-en-1-yl, but-3-en-1-yl, 1-methylbut-3-en-1-yl and 1-methylbut-2-en-1-yl. Alkynyl is, for example, ethynyl, propargyl, but-2-yn-1-yl, but-3-yn-1-yl, 1-methylbut-3-yn-1-yl. Multiple bonds may be at any position per unsaturated group. Cycloalkyl is a carbocyclic saturated ring system having, for example, three to six carbon atoms, such as cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl. Similarly, cycloalkenyl is monocyclic alkenyl having, for example, three to six carbocyclic members, such as cyclopropenyl, cyclobutenyl, cyclopentenyl and cyclohexenyl, wherein the double bond can be in any position. Halogen is fluorine, chlorine, bromine or iodine.

Unless otherwise specified, the term "aryl" as used herein includes, but is not limited to, phenyl, naphthyl, The term "heterocyclyl" includes but is not limited to saturated or unsaturated non-aromatic cyclic groups Etc., also including, but not limited to, heteroaryl, i.e., aromatic cyclic groups containing, for example, 3 to 6 ring atoms of which 1 to 4 (e.g., 1,2, 3, or 4) heteroatoms are selected from oxygen, nitrogen, and sulfur, and optionally also benzo ring fused, for example

If a group is substituted by a group, this is understood to mean that the group is substituted by one or more identical or different radicals selected from those mentioned. The same or different substitution characters contained in the same or different substituents are independently selected and may be the same or different. The same applies to ring systems formed from different atoms and units. Also, the scope of the claims will exclude those compounds known to those skilled in the art to be chemically unstable under standard conditions.

In addition, the phrase "substituted with at least one group" as used herein means substituted with, for example, 1,2, 3, 4 or 5 groups, unless otherwise specified; groups not labeled for a particular attachment position (including heterocyclyl, aryl, etc.) may be attached at any position, including the position attached to C or N; if it is substituted, the substituents can likewise be substituted in any position, provided that the bond rules are complied with. Heteroaryl as substituted by 1 methyl groupCan representAnd the like.

Depending on the nature of the substituents and the manner in which they are attached, the compounds of formula I and their derivatives may exist as stereoisomers. Stereoisomers may be obtained from the mixtures obtained in the preparation by customary separation methods, for example by chromatographic separation. Stereoisomers can likewise be prepared selectively by using stereoselective reactions and using optically active starting materials and/or auxiliaries. The invention also relates to all stereoisomers contained in formula I but not specifically defined and mixtures thereof.

The compounds of formula I of the present invention may be prepared by standard methods of organic chemistry, for example, by a process for the preparation of said fused ring substituted aromatic compounds comprising the steps of:

a compound of the formula IIInto compounds of the general formula I, depending on the nature of the group Q. These processes are described in particular in patents US 567979791, WO2012/041789, WO2019/101551, WO00/50409, CN105753853A and the like.

Or carrying out cyclization reaction on the compound shown in the general formula IV and the compound shown in the general formula V to obtain the compound shown in the general formula I. Preferably, the reaction is carried out in the presence of a solvent and a base. Among these, the method of using the compound represented by the general formula IV is described in, inter alia, WO 1999/055693.

For example, when Q representsWhen (1) a compound represented by the general formula II andcarrying out a reaction to obtain a compound shown as a general formula II-1, and then carrying out a cyclization reaction with the compound shown as the general formula III-1 to obtain the compound shown as the general formula I-1, wherein the chemical reaction formula is as follows:

(2) reacting a compound of formula II withCarrying out reaction to obtain a compound shown as a general formula II-2, and then carrying out reaction with a compound shown as a general formula III-1 to obtain a compound shown as a general formula I-2; the chemical reaction equation is as follows:

when Q representsReacting a compound shown in a general formula II with a compound shown in a general formula III-2 to obtain a compound shown in a general formula I-3; the chemical reaction equation is as follows:

(4) reacting a compound of formula II withCarrying out a reaction to obtain a compound shown as a general formula II-3, and then carrying out a cyclization reaction with the compound shown as the general formula III-3 to obtain a compound shown as a general formula I-4, wherein the chemical reaction formula is as follows:

(5) reacting a compound of formula II withCarrying out reaction to obtain a compound shown as a general formula II-2, and then carrying out reaction with a compound shown as a general formula III-4 to obtain a compound shown as a general formula I-5; the chemical reaction equation is as follows:

or, (6) a compound represented by the general formula I-6 and R₆' -Hal is subjected to substitution reaction to obtain a compound shown as a general formula I-7; the chemical reaction equation is as follows:

wherein L is₁、L₂、L₃、L₄、L₅、L₆And L₇Each independently represents a C1-C6 alkyl or aryl group, preferably methyl, ethyl or phenyl; hal independently represents halogen, preferably chlorine, iodine; r₆' represents R₆Groups other than hydrogen; other substituents R₁、R₂、R₆、R₇、R₈、Q₁、Q₂、Q₃、Q₄、Q₅The definitions of Y, Z and M are as previously described.

Preferably, the first step in step (1) and the first step in step (4) are both carried out in the presence of a solvent.

Preferably, the second step in the step (1), (2), (4), (5) and (6) are all carried out in the presence of a base and a solvent.

Preferably, said step (3) is carried out in the presence of an acid.

The base is selected from inorganic bases (e.g. K)₂CO₃、Na₂CO₃、Cs₂CO₃、NaHCO₃、KF、CsF、KOAc、AcONa、K₃PO₄t-BuONa, EtONa, NaOH, KOH, NaOMe, etc.) or an organic base (e.g., pyrazole, triethylamine, DIEA, etc.).

The solvent is at least one selected from DMF, DMA, methanol, ethanol, acetonitrile, dichloroethane, DMSO, Dioxane, dichloromethane, toluene or ethyl acetate.

The acid is selected from acetic acid, hydrochloric acid or sulfuric acid.

In addition, when QSubstituent Q of (1)₁、Q₂、Q₃At least one is S or Q₄、Q₅When at least one is S, it may also be represented by the corresponding QThe compound is used as raw material in Lawson reagentOr by conventional sulfur substitution in the presence of phosphorus pentasulfide.

A herbicide composition comprising a herbicidally effective amount of at least one of said fused ring substituted aromatic compounds, preferably together with a formulation adjuvant.

A method of controlling weeds, comprising applying a herbicidally effective amount of at least one of said fused ring substituted aromatic based compounds or said herbicidal composition to a plant or to a weed locus.

The application of at least one of the condensed ring substituted aromatic compounds or the herbicide composition in controlling weeds is preferably used for controlling weeds in crops of useful plants, wherein the crops of useful plants are transgenic crops or crops treated by genome editing technology.

The compounds of the formula I according to the invention have outstanding herbicidal activity against a large number of economically important monocotyledonous and dicotyledonous harmful plants. The active substances according to the invention are also effective against perennial weeds which grow from rhizomes, or other perennial organs and are difficult to control. In this connection, it is generally immaterial whether the substance is used before sowing, before germination or after germination. Mention is made in particular of representative examples of the monocotyledonous and dicotyledonous weed groups which the compounds of the invention can control, without being restricted to a defined species. Examples of weed species for which the active substance acts effectively include monocotyledons: annual avena, rye, grass, alopecurus, farris, barnyard grass, digitaria, setaria and sedge, and perennial agropyron, bermudagrass, cogongrass and sorghum, and perennial sedge.

With regard to dicotyledonous weed species, the action can be extended to species such as the annual cleavers, viola, veronica, picea, chickweed, amaranthus, sinapis, ipomoea, sida, matricaria and abutilon species, and the perennial weeds cyclocarya, thistle, sorrel and artemisia. The active substances according to the invention are effective in controlling harmful plants, such as barnyard grass, sagittaria, alisma, eleocharis, saccharum and cyperus, in this particular condition of sowing of rice. If the compounds of the present invention are applied to the soil surface before germination, seedlings of weeds can be completely prevented before the weeds grow out, or the weeds stop growing when they grow out of cotyledons and finally die completely after three to four weeks. The compounds of the invention are particularly active against plants such as, for example, alpinia, sesamum indicum, polygonum convolvulus, chickweed, veronica vinifera, veronica albo, viola tricolor and amaranth, cleavers and kochia.

Although the compounds of the invention have excellent herbicidal activity against monocotyledonous and dicotyledonous weeds, they are not at all harmful or only insignificantly harmful to the important economic crop plants, such as wheat, barley, rye, rice, maize, sugar beet, cotton and soybean. Especially good compatibility with cereal crops such as wheat, barley and maize, especially wheat. The compounds according to the invention are therefore very suitable for selectively controlling unwanted vegetation in agricultural crops or ornamental plants.

Due to their herbicidal properties, these active substances can be used for controlling harmful plants in the cultivation of genetically engineered plants which are known or are to occur. Transgenic plants often have advantageous traits, such as resistance to specific insecticides, particularly to specific herbicides, resistance to plant diseases or to microorganisms pathogenic to plant diseases, such as specific insects or microorganisms of fungi, bacteria or viruses. Other specific traits are related to the conditions of the product, such as quantity, quality, storage stability, composition and specific ingredients. Thus, it is known that the resulting transgenic plant products have an increased starch content or an improved starch quality or a different fatty acid composition.

The compounds of the formula I according to the invention or their salts are preferably used for economically important transgenic crops and ornamentals, for example cereals, such as wheat, barley, rye, oats, millet, rice, cassava and maize, or for the cultivation of sugar beet, cotton, soybean, rapeseed, potato, tomato, pea and other vegetable plants. The compounds of the formula I are preferably used as herbicides for cultivating useful plants which are resistant to the action of the herbicide or which are resistant to the toxic action of the herbicide by genetic engineering.

Conventional methods for breeding plants having improved shape over known plants include, for example, conventional mating methods and mutant breeding. In other words, new plants with improved traits may be obtained by means of methods of genetic engineering (see, for example, EP-0221044A, EP-0131624A). For example, several methods have been described:

to improve starch synthesis in plants, crop plants are altered by genetic engineering (e.g. WO 92/11376, WO 92/14827, WO 91/19806);

transgenic crop plants which are resistant to particular herbicides, to glufosinate herbicides (e.g. EP-0242236A, EP-0242246A) or to glyphosate-type herbicides (WO 92/00377), or to sulfonylurea-type herbicides (EP-0257993A, US-5013659A);

transgenic crop plants, such as cotton, which produce Bacillus thuringiensis toxins (Bt toxins) which protect against attack on plants by specific pests (EP-0142924A, EP-0193259A);

-transgenic crop plants with improved fatty acid composition (WO 91/13972).

A number of molecular biotechnologies are known which enable the production of transgenic plants with improved traits (see, for example, Sambrook et al, 1989, molecular amplification, second edition of the laboratory Manual, Cold spring harbor laboratory publications in USA, Cold spring harbor, New York; or Winnacker "Gene und Klone" [ genes and clones ], VCH Weinheim, second edition 1996 or Christou, "trends in plant science" 1(1996)423- "431)). In order to carry out the manipulation of genetic engineering, it is possible to introduce nucleic acid molecules into plasmids, which undergo mutations or sequence changes by recombination of DNA sequences. Using standard methods as described above, it is possible, for example, to exchange substrates, remove partial sequences or add natural or synthetic sequences. In order to ligate the DNA fragments to each other, it is possible to attach a binder or a linker to the fragments.

Plant cells of reduced activity gene products can be prepared, for example, by expressing at least one suitable antisense-RNA, sense-RNA to achieve a cosuppression effect, or by expressing at least one suitably configured ribozyme which specifically cleaves transcripts of the gene products.

For this purpose, it is possible to use DNA molecules which contain the entire coding sequence of the gene product, including any flanking sequences which may be present, and to use DNA molecules which contain only a part of the coding sequence which has to be long enough to achieve an antisense effect in the cell. Sequences that are highly homologous but not identical to the coding sequence of the gene product may also be used.

When expressing the nucleic acid molecule in a plant, the synthetic protein can be localized in any desired plant cell compartment. However, for localization in a specific chamber, it is possible, for example, to link the coding region to a DNA sequence in order to ensure localization in a specific location. These sequences are known to those skilled in the art (see, for example, Braun et al, EMBO J.11(1992) 3219-3227; Wolter et al, Proc. Natl. Acad. Sci. USA 85(1988), 846-850; Sonnewald et al Plant J.1(1991), 95-106).

Transgenic plant cells can be recombined into whole plants using known techniques. The transgenic plant may be of any desired plant variety, i.e., monocotyledonous and dicotyledonous plants. In this way, it is possible to obtain transgenic plants with improved traits by overexpressing, inhibiting or suppressing homologous (═ natural) genes or gene sequences, or by expressing heterologous (═ external) genes or gene sequences.

When the active substances according to the invention are used on transgenic crops, in addition to the harmful-plant-inhibiting effects observed on other crops, special effects are often observed on the corresponding transgenic crops, for example an improved or enlarged spectrum of weed control, improved application rates in the application, preferably a good combination of resistance of the transgenic crop and herbicide performance, and an influence on the growth and yield of the transgenic crop plants. The invention therefore also provides for the use of the compounds as herbicides for controlling harmful plants in transgenic crop plants.

In addition, the compound of the invention can obviously regulate the growth of crop plants. These compounds are used to target the control of plant components and to promote harvesting, such as desiccation and stunting of plants, by regulating the metabolism of plants involved. They are also suitable for regulating and inhibiting undesirable vegetation without destroying the growth of the crop plants. Inhibiting plant growth plays a very important role in many monocotyledonous and dicotyledonous crop plants, since this reduces or completely prevents lodging.

The compounds of the present invention can be applied using general formulations, and wettable powders, concentrated emulsions, sprayable solutions, powders or granules can be used. Thus the present invention also provides herbicidal compositions comprising compounds of formula I. The compounds of formula I can be formulated in a variety of ways depending on the usual biological and/or chemical physical parameters. Examples of suitable formulation choices are: wettable Powders (WP), water Soluble Powders (SP), water soluble concentrates, Emulsion Concentrates (EC), emulsions dispersed in water (EW), for example, oil-in-water and water-in-oil (EW), sprayable solutions, Suspension Concentrates (SC), dispersible oil suspensions (OD), suspensions with oil or water as diluent, solutions of miscible oils, powders (DP), Capsule Suspensions (CS), core (cutting) compositions, granules for spreading and soil application, spray granules, coated granules and absorbent granules, water dispersible granules (WG), water Soluble Granules (SG), ULV (ultra low volume) formulations, microcapsules and wax preparations. These individual formulation types are known and described in, for example, Winnacker-Kuchler, "Chemische Techologie" [ Chemicals Process ], Vol.7, C.Hauser Verlag Munich, 4 th edition 1986; wade van Valkenburg, "Pesticide Formulations," Marcel Dekker, n.y., 1973; martens, "Spray Drying" handbook, 3 rd edition 1979, g.

The necessary formulation auxiliaries, such as inerts, surfactants, solvents and other additives, are likewise known and are described in the documents mentioned below, for example in Watkins, "handbook of powdered diluents pesticides and carriers", second edition, Darland book Caldwell n.j.; h.v.01phen, "entry to clay colloid chemistry," second edition, j.wiley and Sons, n.y.; marsden, second edition "solvent guide", Interscience, n.y.1963; "annual report of detergents and emulsifiers" by McCutcheon, MC issues, Ridgewood n.j.; sisley and Wood, "surfactant encyclopedia", chemical publishing company, n.y.1964;is/are as follows[ ethylene oxide adduct surfactant]Uss.verlagageell.stuttgart 1976; "Chemische technology" by Winnacker-Kuchler [ chemical Process]Volume 7, c.hauser Verlag Munich, 4 th edition 1986.

Wettable powders can be uniformly dispersed in water and, in addition to the active substance, include diluents or inert substances, ionic and nonionic surfactants (wetting agents, dispersants), such as polyethoxylated alkylphenols, polyethoxylated fatty alcohols, polyoxyethylated fatty amines, fatty alcohol polyglycol ether sulfates, alkylsulfonates, alkylphenylsulfonates, sodium lignosulfonates, sodium 2,2 '-dinaphthylmethane-6, 6' -disulfonate, sodium dibutylnaphthalenesulfonate or sodium oleoylmethyltaurate. To prepare wettable powders, the active substances of the herbicides are finely ground, for example using customary instruments, such as hammer mills, fan mills and jet mills, with simultaneous or sequential incorporation of the adjuvants.

Emulsions are prepared by dissolving the active substance in an organic solvent, such as butanol, cyclohexanone, dimethylformamide, xylene or higher boiling aromatics or hydrocarbons or mixtures of solvents, and adding one or more ionic and/or nonionic surfactants (emulsifiers). Examples of emulsifiers which may be used are calcium alkylarylsulfonates, for example calcium dodecylbenzenesulfonate, or nonionic emulsifiers, for example polyglycol esters of fatty acids, alkylarylpolyglycol ethers, fatty alcohol polyglycol ethers, propylene oxide-ethylene oxide condensation products, alkyl polyethers, sorbitan esters, for example sorbitan fatty acid esters, or polyoxyethylene sorbitan esters, for example polyoxyethylene sorbitan fatty acid esters.

The active substance and finely divided solid substances, for example talc, natural clays such as kaolin, bentonite and pyrophyllite, or diatomaceous earth, are ground to give a powder. Water or oil based suspensions may be prepared, for example, by wet milling using a commercially available bead mill, with or without the addition of a surfactant of the other formulation type described above.

For preparing emulsions, for example oil-in-water Emulsions (EW), it is possible to use aqueous organic solvents, using stirrers, colloid mills and/or static mixers, and, if desired, to add surfactants of another formulation type as described above.

Granules are prepared by spraying the active substance onto the adsorbate, granulating with inert material, or concentrating the active substance onto the surface of a carrier, for example sand, kaolinite, and granulating the inert material with a binder, for example polyvinyl alcohol, sodium polyacrylate or mineral oil. Suitable active substances can be granulated by the process for preparing fertilizer granules, if desired mixed with fertilizers. The preparation of water-suspendable granules is carried out by customary methods, for example spray-drying, fluidized-bed granulation, millstone granulation, mixing using high-speed mixers and extrusion without solid inert materials.

For the preparation of granules using a millstone, a fluidized bed, an extruder and Spray coating, see the following processes, for example "Spray Drying handbook", third edition 1979, g.goodwin ltd, london; browning, "Agglomeration", chemical and engineering 1967, page 147 ff; "Perry's handbook of Engineers of chemistry", fifth edition, McGraw-Hill, New York 1973, pages 8-57. If preparations for crop protection products are to be known, see, for example, G.C. Klingman, "Weed Control as a Science", John Wiley and Sons, New York, pages 196181-96 and J.D. Freyer, S.A. Evans, "Weed Control Manual", fifth edition, Blackwell Scientific rules, Oxford university 1968, page 101-.

Agrochemical formulations generally comprise from 0.1 to 99%, in particular from 0.1 to 95% by weight of active substance of formula I. The concentration of active substance in wettable powders is, for example, from about 10 to 99% by weight, with usual formulation components making up the remainder to 100% by weight. The concentration of the active substance in the emulsion concentrate may be about 1 to 90%, preferably 5 to 80% by weight. Powder formulations contain from 1 to 30% by weight of active, usually preferably from 5 to 20% by weight of active, whereas sprayable solutions contain from about 0.05 to 80%, preferably from 2 to 50% by weight of active. The content of active substance in the aqueous suspension granules depends primarily on whether the active substance is liquid or solid, and the auxiliaries, fillers and the like used in granulation. The content of active substance in the water-suspendable granule formulation is, for example, between 1 and 95% by weight, preferably between 10 and 80% by weight.

The active substance formulations mentioned may additionally comprise tackifiers, wetting agents, dispersants, emulsifiers, penetrants, preservatives, antifreezes, solvents, fillers, carriers, colorants, antifoams, evaporation inhibitors and generally customary pH and viscosity regulators in all cases.

On the basis of these formulations, it is also possible to mix them with other insecticide active substances, such as insecticides, acaricides, herbicides and fungicides, and also with safeners, fertilizers and/or plant growth regulators, either premixed or mixed in containers.

Suitable active substances which can be mixed with the active substances according to the invention in a compounded or tank-mixed formulation are, for example, the substances known from "the world Wide Specification of New agricultural chemical products", from the national agricultural science and technology Press, 2010.9 and the documents cited therein. For example, the herbicidal active substances mentioned below may be mixed with the mixtures of the formula I (remarks: name of the compound, either by common name according to the International organization for standardization (ISO), or by chemical name, where appropriate with a code number): acetochlor, butachlor, alachlor, propisochlor, metolachlor, s-metolachlor, pretilachlor, propyzamide, pretilachlor, napropamide, R-levulinyl-propyzamide, propanil, mefenacet, dibenzamide, diflufenican, flumetsulam, bromobutyrolac, dimethenamid, mefenacet, metazachlor, isoxaflutole, ryegrass methyl ester, loflutolane, diacrylamide, pethoxamide, butachlor, propisochlor, cyprosulfamide, flumetsulam, heptanoyl, isobutramine, propyzamide, terbutamid, dimethenamid, larvamide, trimethylcyclam, clofenamid, propyzamide, penoxulamide, carpronide, diflormid, trinitrol, butachlor, butafenacet, butachlor, benfluralin, bencarbzamide, pencyhalonil, metolachlor, bencarbzamide, pencyhalonil, butachlor, benfluralin-bencarbzachlor, bencarbzamide, bencarb-N-P-N-P-N-P-N-, Grazing amine, bensulfuron, quinoxalamine, bensulfuron-methyl, naproxen, acetochlor, naphazel, thiachlor, pyraflufen, bensulfuron-methyl, prochloraz, clofenamide, butamidam, flupiram, atrazine, simazine, prometryn, cyanazine, simetryn, ametryn, prometryn, ipratron, flurazin, terbutryn, triazineone-flumetsulam, ciprofloxacin, glycazine, pradapazine, prometryn, simatong, azidezin, diuron, isopentetryn, cycloprozine, ametryn, terbuthylazine, terbuton, metocloprid, cyanazine, bentazon, clonazine, atrazine, metribuzin, cyanuric acid, indaziflazaflam, chlorsulfuron, meturon, bensulfuron, chlorimuron, tribenuron-methyl, thifensulfuron-methyl, pyrazosulfuron-methyl, sulfosulfuron-methyl, sulfometuron, bensulfuron-methyl, benazol-methyl, bensulfuron-methyl, benazol-methyl, benflurazid, benfluridimethyl, benfluridil, benflurazid, benfluridil, ben, Cinosulfuron, triasulfuron, sulfometuron-methyl, nicosulfuron, ethametsulfuron, amidosulfuron, ethoxysulfuron, cyclosulfamuron, rimsulfuron, azimsulfuron, primisulfuron-methyl, flusulfuron-methyl, flupyrsulfuron-methyl, epoxysulfuron, imazosulfuron, primisulfuron-methyl, prosulfuron, sulfosulfuron, trifloxysulfuron, triflusulfuron, metsulfuron-methyl sodium, flupyrazosulfuron, methisulfuron-methyl, primisulfuron, propysilfuron (Propyrisulfuron), metribusulfuron, acifluorfen-methyl, fomesafen, lactofen, fluoroglycofen-ethyl, oxyfen, prosulfuron, benfuresafen, trifloxysulfuron, metofen-ethyl, metofen, trifloxysulfuron, fluroxypyr, fluridone, benfop, benfluridone, benfurazolin, benfluridone, benfurbenfluridone, benfluridone, benfurin, benfluridone, benfurbenfurbenfurin, benfurbenfurbenfurbenfurbenfurbenfurin, benfluridone, benfurbenfurbenfurbenfurbenfurin, benfurin, benfluridone, benfurin, benfurbenfurbenfurin, benfurbenfurbenfurbenfurbenfurbenfurbenfurbenfurbenfurbenfurbenfurin, benfurin, benfurbenfurbenfurbenfurbenfurin, benfurin, benfurbenfurbenfurbenfurbenfurbenfurbenfurin, benfurin, benfurbenfurin, benfurin, benfurbenfurbenfurbenfurbenfurbenfurbenfurbenfurbenfurin, benfurin, benfurbenfurbenfurin, benfurbenfurbenfurbenfurbenfurin, benfurin, benfurbenfurin, benfurin, benfurbenfurbenfurin, benfurbenfurbenfurbenfurbenfurin, benfurin, benfurbenfurbenfurbenfur, Dimethofen, oxyfluorfen, clofenflurate, Halosafen, chlortoluron, isoproturon, linuron, diuron, sifenuron, fluometuron, benzthiauron, methabenzuron, prosulfuron, sulfosulfuron, clomauron, clodinafuron, clofensulfuron, metoxuron, bromuron, metoxuron, meturon, fensulfuron, prosulfuron, subtilon, cuarone, metolachlor, cycloaroron, cyclouron, thifluuron, buthiuron, kuron, cumuron, metoxuron, methamidothion, metominosulfuron, trifolium, isoxafluron, isoxauron, moneuronon, aniron, methicuron, chloretron, clotururon, teuron, benuron, pennison, phenmedibensulfuron, bensulfuron, benazolin, propham, buthan, thiuron, buthan, benazolin, buthan, benazolin, buthan, benazolin, thiuron, thifenbenazolin, thiuron, thifenbenazolin, thiuron, thifenbenazolin, thiuron, thifenbencarb, thiuron, thifenbencarb, thiuron, thifenbencarb, thiuron, thifenbencarb, Thiobencarb, merthiolane, diclofop, triallate, penoxsulam, pyributicarb, dichlorfon, edifenphos, ethiofen, prosulfocarb, clenbuterol, prosulfocarb, dichotomene, thiobencarb, promethazine, Isopolinate, Methiobencarb, 2, 4-d butyl ester, 2 methyl 4-sodium chloride, 2, 4-d isooctyl ester, 2 methyl 4-chloroisooctyl ester, 2, 4-d sodium salt, 2, 4-d dimethylamine salt, 2 methyl 4-chloroethyl thioester, 2 methyl 4 chloride, 2, 4-d propionic acid, 2, 4-d propionate, 2, 4-d butyric acid, 2 methyl 4-chloropropionic acid, 2 methyl 4-chlorobutyric acid, 2,4, 5-d nasal discharge, 2,4, 5-d propionic acid, 2,4, 5-d butyric acid, 2 methyl 4-chloropropionic acid, 2 methyl 4-d propionic acid, 2-d propionic acid, 2-cloroprionic acid, triclocarb, triclopyr, clorac, aminodiclofenac, metocloprofenac, diclofop-methyl, fluazifop-p-butyl, haloxyfop-methyl, haloxyfop-p-butyl, quizalofop-ethyl, quizalofop-p-ethyl, fenoxaprop-p-ethyl, propaquizafop-ethyl, fenoxaprop-ethyl, clodinafop-ethyl, benazolin, clodinafop-ethyl, haloxyfop-methyl, benazolin, propalaxyl, butyfen-ethyl, chloroethafloxacin, aminofluanid, benazolin, dichlofop-ethyl, methamphetalin, propamocarb-ethyl, benfop-methyl, thiophosphine, pirimiphos-methyl, benfop-ethyl, benazolin, benfop-methyl, imax-methyl, mefenofos, mefeno, Imazamox ammonium salt, imazapic acid, imazamethabenz ester, fluroxypyr, clopyralid, picloram, triclopyr, dithiopyr, haloxydine, triclopyril, thiazopyr, fluridone, aminopyralid, diflufenzopyr, butoxyethyl triclopyr, Clodinate, sethoxydim, clethodim, cycloxydim, clethodim, topramezone, Buthidazole, metribuzin, hexazinone, metamitron, metribuzin, amitridione, Amibuzin, bromoxynil, octanoyl ioxynil, dichlobenitrile, pyraclonil, hydroxybensulam, Iodobonil, flumetsulam, penoxsulam, clofenapyr, pyraclonil, pyraflufen-ethyl, pyraoxystrobin, flumetsulam, pyraclonil, pyraoxystrobin, isoxathion, pyriftalid, pyriminobac-methyl, pyrithiobac-methyl, benzobicylon, mesotrione, sulcotrione, Tembotrione, Tefuryltrione, Bicyclopyrone, ketodradox, isoxaflutole, isoxaclomazone, fenoxasulfofone, methiozoline, isopyrafen, pyraflufen, pyrazote, difenzoquat, pyrazoxazole, pyroxaflutole, pyroxsulam, pyraclofos, pyraclonil, amicarbazone, carfentrazone, flumiclone, sulfentrazone, bencarane, bisphenomezone, butafenacil, isoxaflutole, cyclam, triclopyr, fluroxypyr, flumethazine, parnaprox, flumiclone, flumethol, carfentrazone, carzone, carfentrazone, tebufenozide, tebufadix, tebufenozide, tebufalin, tebufenozide, tebufalin, fluazifop-methyl, pyriminostrobin, bromopicrin, didaphylm, pyridaben, Pyridafol, quinclorac, chloroquine, bentazon, pyridate, oxaziclomefone, benazolin, clomazone, isoprox, isoproxypyrim, propyribac, cumylfen, clomazone, sodium chlorate, thatch, trichloroacetic acid, monochloroacetic acid, hexachloroacetone, tetrafluoropropionic acid, mequat, bromophenol oxime, triazasulam, imazazole, flurtamone, mesotrione, ethofumesate, pyrimethanil, clodinafop-methyl, clodinium, pyributaine, benfurazolin, meton, metamitron, metolachlor, dichlorvofen, triclopyr, aloac, Dietmquat, Etpronil, ipriflam, iprimazam, iprodione, Trizopyr, Thiaclonifen, chlorpyrifos, pyradifquat, chlorpyrifos, propiram, pyradifurone, pyradifon, pyradifurone, pyrazone, thion, pyrazone, thiothifluzone, pyrazone, thiothifluzone, thion, thiothifluzone, thion, thiobenflurazolidone, thion, thifluzone, thion, thifluzone, thidiazuron, thidiaz, Clomazone, fenclorim, cloquintocet-mexyl, mefenpyr-diethyl, DOWFAUC, UBH-509, D489, LS 82-556, KPP-300, NC-324, NC-330, KH-218, DPX-N8189, SC-0744, DOWCO535, DK-8910, V-53482, PP-600, MBH-001, KIH-9201, ET-751, KIH-6127 and KIH-2023.

When used, the commercially available formulations are diluted in the usual manner, if desired, for example in wettable powders, concentrated emulsions, suspensions and granules suspended in water, using water. Powders, granules for soil application or solutions for spreading and spraying generally do not require further dilution with inert substances before use. The required amount of the compound of formula I to be used varies with the external conditions, such as temperature, humidity, the nature of the herbicide used, etc. It can vary to a large extent, for example between 0.001 and 1.0kg a.i./ha, or more active substance, but preferably between 0.005 and 750g a.i./ha, in particular between 0.005 and 250g a.i./ha.

Detailed Description

The following examples are intended to illustrate the invention and should not be construed as limiting it in any way. The scope of the invention is indicated by the appended claims.

In view of the economic and diversity of the compounds, we prefer to synthesize some of the compounds, a selection of which are listed in table 1 below. Specific compound structures and corresponding compound information are shown in table 1. The compounds in table 1 are only for better illustrating the present invention, but not for limiting the present invention, and it should not be understood to limit the scope of the above-mentioned subject matter of the present invention to the following compounds for those skilled in the art.

Table 1 Structure of Compounds and methods of use thereof¹HNMR

Several methods for preparing the compounds of the present invention are illustrated in the schemes and examples below. The starting materials are commercially available or can be prepared by methods known in the literature or as shown in detail. It will be appreciated by those skilled in the art that other synthetic routes may also be utilized to synthesize the compounds of the present invention. Although specific starting materials and conditions for the synthetic route are described below, they can be readily substituted with other similar starting materials and conditions, and variations or modifications of the preparation process of the present invention, such as various isomers of the compounds, are included in the scope of the present invention. In addition, the preparation methods described below may be further modified in accordance with the present disclosure using conventional chemical methods well known to those skilled in the art. For example, protecting the appropriate groups during the reaction, and the like.

The following process examples are provided to facilitate a further understanding of the methods of preparation of the present invention, and the particular materials, species and conditions used are intended to be further illustrative of the invention and are not intended to limit the reasonable scope thereof. The reagents used in the synthesis of the compounds indicated in the following table are either commercially available or can be readily prepared by one of ordinary skill in the art.

Examples of representative compounds are given below, and the synthesis of other compounds is similar and will not be described in detail herein.

1. Synthesis of Compound 2

(1) 2-0(20g,91.5mmol,1.0eq) was added to 150 ml of DMF, and then NCS (13.4g,100.7mmol,1.1eq) was slowly added to the reaction mixture at 35 ℃. After the addition, the reaction was stirred at 35 ℃ for 1.5 hours and the reaction was essentially complete by LCMS. The reaction was poured into 100ml of HCl (1M) and extracted with dichloromethane, the organic phase was washed with saturated brine (100ml x 3), the organic phase was concentrated to give crude 2-1(26g, crude) (yellow oil) which was directly put to the next step.

(2) To 10mL of DCM was added 2-1(1g), Et₃N (600mg,6.0mmol,1.5eq), then a (605mg,4.8mmol,1.2eq) was added to the reaction at 0 ℃. The temperature was slowly raised to 20 ℃ and after 16 hours of reaction the product was detected by LCMS. To the reaction mixture was added 10ml of water, extracted with dichloromethane (10ml x 3), the organic phase was dried over anhydrous sodium sulfate, concentrated and the crude product was purified by column chromatography to give 2-2(400mg,1.2mmol, 30% yield).

(3) 2-2(400mg,1.2mmol,1.0eq), Fe powder (202mg,3.6mmol,3eq), NH were added to 5ml of EtOH in that order₄Cl (127mg,2.4mmol,2eq) and water (1 ml). Then the reaction solution reacts for 2 hours at the temperature of 80 ℃, and the LCMS detects that the raw materials disappear, and the main peak is the product peak. After cooling, the reaction solution was filtered with celite, concentrated to remove ethanol, then water (10ml) was added, ethyl acetate was extracted and concentrated to obtain a black crude product, which was purified by column chromatography to obtain 2-3(300mg,0.96mmol, 80% yield).

(4) 2-3(0.3g,0.96mmol,1.0eq) and b (165mg,1.06mmol,1.1eq) were dissolved in 5ml dioxane, and the reaction solution was heated at 110 ℃ for 30 minutes. LCMS detects that the raw materials are basically reacted completely, and the main peak is the product. The solvent was concentrated and the crude product was isolated by column chromatography to give 2-4(0.4g,0.92mmol, 96% yield).

(5) C (217mg,0.97mmol,1.05eq) and AcONa (38mg,0.46mmol,0.5eq) were added to 3ml of DMF, and then the reaction mixture was reacted at 60 ℃ for 10 minutes after 2 to 4(0.4g,0.92mmol,1.0eq) was slowly added thereto. LCMS detected product. After adding water (10ml) to the reaction mixture, extraction was performed with ethyl acetate, the organic phase was washed with saturated brine (20 ml. times.1), and the crude product was separated by column chromatography after concentration of the organic phase to give compound 2(0.3g, 0.64mmol, 70% yield).

2. Synthesis of Compound 49

In a 50ml eggplant-shaped bottle, compound 2(1.0eq,100mg) was dissolved in 49-1(5V), and tetraisopropyl titanate (20% mol) was added. After the reaction solution reacts for 1-2 hours at 80 ℃, the raw materials disappear by LCMS detection, and the main peak is the product. The reaction solution was directly stirred with silica gel, and the crude product was isolated and purified by column chromatography to give compound 49(31mg, 22% yield) (pale yellow solid).

3. Synthesis of Compound 209

(1) 2-3(1.0eq) and 210-7(1.0eq) of the starting material were added to 10V of acetic acid, and the reaction mixture was reacted at 125 ℃ for 1 hour. The carboxylic acid was removed by spin drying and used directly in the next step.

(2) 209-1(1.0eq), methyl iodide (4.0eq) and K were added to 5V DMF in that order₂CO₃(2.0eq), then the reaction solution was reacted at 25-30 ℃ for 16 hours until completion of the reaction by LCMS detection. After extraction with ethyl acetate in water, the extract was washed with saturated brine and purified by column chromatography to obtain compound 209 (30% yield).

4. Synthesis of Compounds 210 and 212

(1) Fuming nitric acid (18.62g,0.296mol,3eq) was added gradually to concentrated sulfuric acid (87g,0.887mol,9eq) at 0 ℃. After the completion of the addition, compound 210-1(20g,98.52mmol,1eq) was added to the above solution in portions at 0 ℃ and then the reaction mixture was reacted at 0 ℃ for 8 hours. LCMS detected a small amount of starting material remaining with a major new peak. The reaction solution was slowly added to an ice-water mixture, extracted with ethyl acetate, washed with saturated sodium bicarbonate until the pH became slightly alkaline, dried over anhydrous sodium sulfate, concentrated, and column purified to give compound 210-2(16g, 65% yield).

(2) 210-2(16g,64.5mmol, 1.0eq) was added to 160 ml of EtOH, and NH was added dropwise to the reaction mixture at 0 deg.C₂OHCl (4.93g,70.97mmol,1.1eq) in water (20 ml). After the completion of the dropwise addition, the reaction mixture was stirred at 0 ℃ for 3 hours. LCMS detection showed almost complete consumption of starting material with a major new peak. The reaction was concentrated to remove most of the ethanol and poured into 100ml of water, and solids precipitated, filtered, and the filter cake was washed with water and dried to give 210-3(15g, 88% yield).

(3) 210-3(10g,38.02mmol,1.0eq) was added to 150 ml of DMF, and then NCS (5.58g,41.82mmol,1.1eq) was slowly added to the reaction mixture at 35 ℃. After the addition, the reaction mixture was stirred at 35 ℃ for 2 hours. LCMS detected substantial reaction completion of starting material. The reaction was poured into 100ml of water, extracted with dichloromethane, the organic phase washed with saturated brine (100ml x 3), and the organic phase was concentrated to give crude 210-4(11g, 97% yield) which was directly put to the next step.

(4) To 200 mL of DCM was added 210-4(11g,36.98mmol,1.0eq), Et₃N (5.61g,55.47mmol,1.5eq), then a (5.13g,40.68mmol,1.1eq) was added to the reaction mixture at 0 ℃. The reaction was carried out at 0 ℃ for 1 hour, then slowly warmed to room temperature, and reacted at room temperature overnight. LCMS detected product. To the reaction was added 100ml of water, extracted with dichloromethane (100ml x 3), the organic phase was dried over anhydrous sodium sulfate, concentrated and the crude product was purified by column chromatography to give 210-5(4.7g, 32% yield).

(5) 210-5(4.7g,12.14mmol,1.0eq), Fe powder (2.03g,36.42mmol,3eq), NH were added to 200 ml of EtOH in sequence₄Cl (1.95g,36.42mmol,3eq) and water (50 ml). Then the reaction solution reacts for 1 hour at the temperature of 80 ℃, and the LCMS detects that the raw materials disappear, and the main peak is the product peak. The reaction mixture was filtered through celite, concentrated to remove ethanol, then water (100ml) was added, extracted with ethyl acetate and concentrated to give 210-6(4.2g, 96% yield).

(6) 210-6(4.25g,11.9mmol,1.0eq) and 210-7(2.48g,11.9mmol,1.0eq) were added to 50ml of acetic acid, and the reaction mixture was reacted at 125 ℃ for 0.5 to 1 hour. LCMS detects that the raw materials are basically reacted completely, and the main peak is the product. The solvent was concentrated to give crude 210-8(9 g).

(7) 210-8(9g,17.30mmol,1.0eq), K were added to 100ml DMF in succession₂CO₃(7.17g,51.9mmol,3eq), methyl iodide (7.37g, 51.9mmol,3eq) was added dropwise at room temperature, and the reaction mixture was reacted at 35 ℃ for 3 hours. LCMS detection of productMolecular weight of product, and raw material peak basically disappears. The reaction was extracted with ethyl acetate and water, the organic phase was washed 3 times with saturated aqueous sodium chloride, the organic phase was dried and concentrated, and the product 210(2g, red solid) was obtained by column purification.

(8) To a 20mL microwave tube were added 10mL of DMF, 210(0.5g,0.3935mmol,1.0eq), CuCN (167.6mg,1.87mmol,2eq), drum N in that order₂Protecting, reacting at 150 ℃ by microwave for 1 hour, basically finishing the reaction of liquid quality detection raw materials, extracting a main peak of a product, using ethyl acetate and water to extract a reaction liquid, using saturated sodium chloride aqueous solution to wash an organic phase for 3 times, drying and concentrating the organic phase, and purifying by a column to obtain a product, namely the compound 212(0.1g, yield 22%).

5. Synthesis of Compound 372

(1) In a 50mL bottle, 2 to 1(1.0eq) and dichloromethane (10V) as a solvent were put, triethylamine (1.5eq) was added dropwise in an ice-water bath, and then 372 to 1(1.1eq) was added thereto, and the mixture was warmed to room temperature and stirred for reaction overnight. After the reaction, the reaction solution is washed by water, and an organic phase is collected and is separated by stirring (DCM: MeOH) to obtain a product 372-2 with the yield of 42%.

(2) Putting the product 372-2(1.0eq) obtained in the previous step, a solvent dichloromethane (5V) and a catalytic amount of DMF (10% mol) into a 50mL bottle, dropwise adding thionyl chloride (2.0eq) under a water bath, and after the addition is finished, heating to reflux for 2 hours. After the reaction, the solvent and excess thionyl chloride were spun off under reduced pressure, the residue was dissolved in dichloromethane (5V), methanol (10.0eq) was added dropwise, and the temperature was raised to reflux reaction. After the reaction is finished, the solvent and the methanol are firstly removed by decompression, the remainder is dissolved by adding ethyl acetate, and brine is used for washing. The organic phase is collected and sent to be separated to obtain 372-3 of the product with 85 percent of yield.

(3) Putting the product 372-3 obtained in the previous step, solvent ethanol and water (5:1), Fe powder (3.0eq) and ammonium chloride (2.0eq) in a 50mL bottle, heating to 80 ℃, and stirring for reaction for 1 h. After the reaction is finished, filtering the diatomite, collecting filtrate, spin-drying, adding ethyl acetate to dissolve residues, washing the residues with brine, collecting an organic phase, drying and spin-drying to obtain a product 372-4 with the yield of 40%.

(4) Putting the 372-4 product obtained in the previous step, acetic acid (10V) solvent and cyclic lactone 210-7(1.1eq) into a 50mL bottle, and heating to 125 ℃ for reaction for 0.5 hour. After the reaction is finished, the solvent is dried by spinning under reduced pressure, and the residue is dissolved by adding DMF for later use.

(5) Methyl iodide (3.0eq) and anhydrous potassium carbonate (5.0eq) were directly added to the reaction flask in the previous step, and then the reaction solution was reacted overnight at 30 ℃. After the reaction is finished, water is added into the reaction liquid for dilution, then ethyl acetate is used for extraction, the organic phase is washed by saturated saline solution, the organic phase is collected and mixed with a sample, and then the product compound 372 is obtained with the yield of 32%.

6. Synthesis of Compound 521

The synthesis method according to the aforementioned 4 th steps (2) and (3) consisting ofTo give compound 521-1, and then add 10ml of DCM521-1(0.4g,1mmol,1.0eq), a (0.126g,1mmol,1.0eq), TEA (0.202g,2mmol,2.0eq), then the reaction was stirred at room temperature for 2 hours, LCMS showed complete reaction, the reaction was concentrated and purified by column chromatography to give 521(0.245g, 50% yield) (white oil).

7. Synthesis of Compound 533

(1) Adding 4eq of trimethyl sulfur iodide and 10V of solvent THF (tetrahydrofuran) into a 100mL three-neck flask, cooling to-20 ℃, dropwise adding 3.3eq of n-butyl lithium under the protection of nitrogen, keeping the temperature and stirring for 30min after the addition is finished, and then dropwise adding a THF solution of 1, 2-cyclopentane epoxide 533-1. After the addition, the temperature was slowly raised to room temperature over 1 hour, and the mixture was stirred at room temperature for 2 hours. After the reaction, water was added to quench and ether was extracted. The organic phase was washed with brine and dried over anhydrous magnesium sulfate. Filtered and concentrated to leave about 10mL for use.

(2) And (3) putting 5.38eq of triethyl orthoacetate and 0.26eq of propionic acid into the bottle in the last step, heating to 145 ℃, and carrying out open reaction to evaporate the generated ethanol. After ethanol was distilled off, the reaction was carried out at 145 ℃ with stirring for 1 hour. After the reaction is finished, cooling to room temperature, adding diethyl ether for dilution, and adding 1M KHSO₄(30mL) the reaction was stirred overnight. The organic phase was separated off and the aqueous phase was extracted with diethyl ether. The organic phases were combined and washed with saturated sodium bicarbonate. And collecting an organic phase, drying the organic phase by using anhydrous sodium sulfate, and then carrying out spin drying to obtain a product 533-3 which is directly used for the next reaction.

(3) In a 50mL bottle, 2-1(1.0eq) and 5V of solvent dichloromethane are put, 2eq of triethylamine is added dropwise in an ice water bath, 533-3(1.2eq) is then added, and the mixture is warmed to room temperature and stirred overnight for reaction. After the reaction is finished, washing with water, collecting an organic phase, mixing with a sample, and separating to obtain a product 533-4.

(4) In a 50mL bottle, 533-4(1.0eq) of the product obtained in the previous step, solvent ethanol and water (5:1), 3eq of Fe powder and 2eq of ammonium chloride are put into the bottle, and the mixture is heated to 80 ℃ and stirred for reaction for 1 h. After the reaction is finished, filtering the diatomite, collecting filtrate, spin-drying, adding ethyl acetate to dissolve residues, washing the residues with brine, collecting an organic phase, drying and spin-drying to obtain a product 533-5.

(5) Putting 533-5(1.0eq) of the product obtained in the previous step and 10V (1.1eq) of acetic acid as a solvent into a 50mL bottle, and heating to 125 ℃ for reaction for 0.5 hour. After the reaction is finished, the solvent is dried by spinning under reduced pressure, and the residue is dissolved by adding DMF for later use.

(6) 3.0eq of methyl iodide and 5eq of anhydrous potassium carbonate are directly added into the reaction bottle in the last step, and then the reaction liquid is reacted at 30 ℃ overnight. After the reaction is finished, water is added into the reaction liquid for dilution, then ethyl acetate is used for extraction, the organic phase is washed by saturated saline solution, the organic phase is collected and mixed with a sample, and then the product compound 533 is obtained.

8. Synthesis of Compounds 541 and 544

(1) 2-3 and 541-1(2.0eq) were added to 20ml of acetic acid, and the reaction mixture was reacted at 125 ℃ for 15 hours. LCMS detects that the raw materials are basically reacted completely, and the main peak is the product. The crude product is separated by column chromatography after the solvent is concentrated to obtain the compound 541 with the yield of 54 percent.

(2) Compound 541, nitroisopropane (1.5eq), and TEA (1.5eq) were added to 20ml of DCM, and then the reaction was allowed to react at room temperature for 10 minutes, and disappearance of the starting material was detected by LCMS. Direct sample application on column purification gave compound 544 (yellow solid) in 56% yield.

9. Synthesis of Compound 545

2-3(1.0eq), 545-1(2.0eq) and glacial acetic acid were added to a single-neck flask, heated to 125 ℃ and stirred for 3 hours. The liquid chromatography detection method comprises the steps of completely reacting raw materials, spin-drying a solvent, dissolving the solvent with ethyl acetate, adding silica gel, stirring, and performing column chromatography analysis and purification to obtain the compound 545 with the yield of 62%.

10. Synthesis of Compound 547

547-1(0.128g,1mmol,1.0eq), 2-3(0.312g,1mmol,1.0eq) were added to 10ml of acetic acid, the reaction was stirred at 120 ℃ for 12 hours, LCMS showed completion of the reaction, the reaction was concentrated, and column chromatography was performed to purify compound 547(0.11g, 26% yield) (white oil).

11. Synthesis of Compound 551

After 2-3(0.312g,1mmol,1.0eq), 551-1(0.165g,1mmol,1.0eq), TEA (0.202g,2mmol,2.0eq), CDI (0.162g,1mmol,1.0eq) were added to 10ml of acetonitrile, the reaction was stirred at 60 ℃ for 1 hour, LCMS showed completion, the reaction was concentrated, and column chromatography was performed to purify the reaction mixture to obtain the product compound 551(0.11g, 26% yield) (white solid).

12. Synthesis of Compound 552

(1) To 20mL of DCM was added 2-3(260mg), Et₃N(3eq)，S-CDI(3.0eq), then the reaction was left to react overnight at room temperature and the disappearance of starting material was detected by LCMS. Direct sample-mixing and column-purification gave 552-1 in 65% yield (yellow solid).

(2) To 20mL of DCM was added 552-1, Et₃N (3eq), propylamine (3eq), and the reaction was then allowed to react at room temperature for 3 hours, and disappearance of the starting material was detected by LCMS. After direct sample-mixing and column-passing purification, compound 552-2 (yellow solid) was obtained with a yield of 52%.

(3) After compound 552-2, potassium carbonate (3eq), and oxalyl chloride (1.1eq) were added to 20ml of DMF, the reaction mixture was reacted for half an hour under ice bath and then heated to 50 ℃ for 1 hour, and disappearance of the starting material was detected by LCMS. Washing with water, extracting with ethyl acetate, and purifying by column chromatography to obtain compound 552 (yellow solid) with yield of 38%.

13. Synthesis of Compound 553

After adding compound 552, propylamine (10eq) to 20ml of DCM, the reaction was allowed to react at room temperature for 3 hours and disappearance of the starting material was detected by LCMS. After direct sample-mixing and column-purification, compound 553 (yellow solid) was obtained in 72% yield.

14. Synthesis of Compound 561

(1) Activated carbon powder (0.25g) was added to the stirred compound 561-2(3.10ml, 25.7mmol) at-20 deg.C (cooled with a dry ice/isopropanol bath) under nitrogen. Compound 561-1(2.55g, 25.7mmol) was dissolved in ethyl acetate (25mL) and slowly added dropwise to the system, with the temperature controlled at 0 ℃ or lower. The reaction is carried out at room temperature overnight, after TLC detection (potassium permanganate color development) of the raw materials is basically completely reacted, the reaction solution is filtered to remove precipitates and active carbon, and a filter cake is washed by ethyl acetate. The filtrate was dried under vacuum at 40 ℃ to give a crude product of compound 561-3(1.8g), which was a yellow hazy oil.

(2) Dissolving compound 2-3(1.5g, 4.8mmol) in concentrated hydrochloric acid (15mL), cooling to-5 deg.C, and slowly adding NaNO dropwise₂(397mg,5.76mmol) at-5 ℃ for 1 hour. Dissolving stannous chloride (2.27g, 11.99mmol) in concentrated hydrochloric acid (5mL), slowly dropwise adding into a reaction system, reacting for 1-2 hours at 0 ℃, completing most of liquid quality detection raw materials, and generating a product with the content of about-75%. 10g of diatomaceous earth was added to the reaction system, followed by vigorous stirring, adjustment of the system pH to about 8 to 9 with a 10% aqueous solution of NaOH at 0 ℃, extraction with dichloromethane twice, drying and concentration of the organic phase, to obtain a crude compound 561-4(1.2 g).

(3) Compound 561-4(1.2g,3.66mmol) was dissolved in anhydrous dichloromethane (50mL) and placed in a 100mL single-necked flask, and formic acid (185mg,4.03mmol) was added dropwise at room temperature and reacted at room temperature overnight. After the reaction of the raw materials is finished, the main peak is the product, and the reaction solution is concentrated at 40 ℃ to obtain a crude product of the compound 561-5(0.8 g).

(4) Dissolving a compound 561-5(0.75g,2.11mmol) in anhydrous acetonitrile (30mL), placing in a 100mL single-neck bottle, cooling to 0 ℃, dropwise adding an acetonitrile (10mL) solution of a compound 561-3(417mg,2.32mmol), controlling the temperature below 10 ℃, dropwise adding triethylamine (87mg,2.16mmol), reacting at 0 ℃ for 30min, then heating to 50 ℃ and reacting for 6-7 h, wherein the liquid detection raw material is completely reacted and intermediate state is generated. 6N HCl (3.16mL,18.97mmol) is dripped into the reaction system, and then the reaction is carried out for 1 hour at 50 ℃, and the product is generated by liquid quality detection. The reaction mixture was concentrated and purified by reverse phase column to give clean compound 561(27mg, yield 3%).

15. Synthesis of Compound 574

(1) To 10mL of DCM was added 552-1(0.3g,0.85mmol,1.0eq), MeNH₂HCl (0.11g,1.7mmol,2.0eq), TEA (0.34g,3.4mmol,4.0eq) and then the reaction was stirred at room temperature for 3 hours, LCMS showed complete reaction, the reaction was concentrated and purified by column chromatography to give product 574-1(0.25g, 76% yield) (white oil).

(2) To 10ml of toluene were added 574-1(0.25g,0.65mmol,1.0eq), 574-2(0.14g,0.71mmol,1.1eq), and TEA (0.08g,0.78mmol,1.2eq), and the reaction was stirred at 100 ℃ for 8 hours, LCMS showed completion of the reaction, and the reaction was concentrated and purified by column chromatography to give product 574(0.03g, 10% yield) (white solid).

16. Synthesis of Compound 575

552-1(1.0eq) and hexahydropyridazine hydrochloride (1.1eq) and triethylamine (3.0eq) were dissolved in DCM (10V) and after completion of the reaction at room temperature for 1 hour, CDI (1.5eq) was added. After the temperature is raised to 45 ℃, the reaction is carried out overnight, the product is controlled, and the product 575 is obtained by mixing the sample and purifying the sample by a column, and the yield is 38%.

17. Synthesis of Compounds 577, 578 and 579

(1) To 10ml of aqueous HBr was added 2-3(0.312g,1mmol,1.0eq), NaNO₂(0.14g,2mmol,2.0eq), adding CuBr (0.284g,2mmol,2.0eq) at 0 ℃, stirring the reaction solution at room temperature for 2 hours, detecting by LCMS to show completion of the reaction, concentrating the reaction solution, extracting with ethyl acetate, washing with saturated saline, evaporating to dryness, and purifying by column chromatography to obtain the product intermediate compound 578-1(0.3g, 85% yield) (yellow solid).

(2) To 10ml of dioxane were added 578-1(0.376g,1mmol,1.0eq), 578-2(0.254g,1mmol,1.0eq), KOAc (0.2g,2mmol,2.0eq), N₂Adding Pd (dppf) Cl under the condition₂(0.1g,0.1mmol,0.1eq) and the reaction was stirred at 80 ℃ for 12 h, LCMS showed complete reaction, concentrated and purified by column chromatography to give intermediate compound 578-3(0.17g, 50% yield) (white oil).

(3) The compound 578-4 was dissolved in 12 vol dioxane, and after slowly adding sodium methoxide solution (1.5eq, 30%) dropwise, the temperature was raised to 100 ℃ for 16 hours, and the reaction was controlled to be complete. Cooling the reaction liquid, performing suction filtration, dissolving the solid by using a 1M hydrochloric acid solution, dissolving the liquid phase by using a 1M hydrochloric acid solution after concentration, combining the two solutions, extracting by using ethyl acetate until no product exists in the water phase, concentrating the organic phase to obtain a solid, pulping and purifying by using petroleum ether and ethyl acetate of which the ratio is 10:1, and filtering and drying to obtain a compound 578-5.

(4) 578-5 was added to 10 volumes of DCE followed by phosphorus oxychloride (3.0eq) and catalytic amount of DMF (5%), and the reaction was allowed to warm to 100 ℃ for 16 hours with controlled completion. Cooling the reaction liquid, concentrating to remove excessive phosphorus oxychloride, then quenching the reaction with water, adjusting the pH value to 8-9 with potassium carbonate, extracting the product with dichloromethane, concentrating, mixing with a sample, and purifying by a column to obtain a compound 578-6.

(5) 1ml of water was added to 10ml of dioxane, and 578-6(0.212g,1mmol,1.0eq), 578-3(0.341g,1mmol,1.0eq), Cs were added₂CO₃(0.652g,2mmol,2.0eq)，N₂Adding Pd (dppf) Cl under the condition₂(0.1g,0.1mmol,0.1eq), the reaction was stirred at 100 ℃ for 12 h, LCMS showed complete reaction, concentrated and purified by column chromatography to give compound 578(0.24g, 50% yield) (white oil).

(6) Compound 578(0.473g,1mmol,1.0eq), KOAc (0.2g,2mmol,2.0eq) was added to 10ml of DMSO, the reaction was stirred at 120 ℃ for 2h, LCMS showed complete reaction, the reaction was concentrated and purified by column chromatography to give compound 577(0.23g, 51% yield) (white oil).

(7) To 10ml of DMF was added compound 577(0.459g,1mmol,1.0eq), K₂CO₃(0.276g,2mmol,2.0eq), IME (0.286g,2mmol,2.0eq), then the reaction was stirred at room temperature for 2 hours, LCMS showed completion of the reaction, concentrated and purified by column chromatography to give compound 579(0.12g, 25% yield) (white oil).

18. Synthesis of Compounds 587 and 588

(1) To 10ml of dioxane were added 587-1(0.1g,1mmol,1.0eq), 578-1(0.376g,1mmol,1.0eq), TEA (0.202g,2mmol,2.0eq), N₂Adding Pd (pph) under the condition₃)₄(0.1g,0.1mmol,0.1eq), CuI (0.019g,0.1mmol,0.1eq), then the reaction was stirred at 100 ℃ for 12 hours, LCMS showed complete reaction, the reaction was concentrated and purified by column chromatography to give 0.19g (49% yield) of the product as a yellow solid.

(2) 587-2(0.394g,1mmol,1.0eq), K was added to 10ml of THF₂CO₃(0.138g,1mmol,1.0eq) and the reaction stirred at room temperature for 2 hours, LCMS showed complete reaction, the reaction was concentrated and purified by column chromatography to give 0.2g (62% yield) of the product as a white oil.

(3) Ac in 10ml₂587-3(0.321g,1mmol,1.0eq), Sarcosine (0.2g,2mmol,2.0eq), (CF) were added to O₃CO)₂O (0.218g,1mmol,1.0eq), then the reaction was stirred at 120 ℃ for 12 h, LCMS showed complete reaction, the reaction was concentrated and purified by column chromatography to give 0.22g (51% yield) of the product as a white oil.

(4) 587(0.44g,1mmol,1.0eq), NCS (0.27g,2mmol,2.0eq) were added to 10ml of DMF and the reaction was stirred at 60 ℃ for 2h, LCMS showed complete reaction and the reaction was concentrated and purified by column chromatography to give 0.1g (20% yield) of the product as a white oil.

19. Synthesis of Compounds 589 and 590

(1) 1ml of water was added to 10ml of dioxane, and 589-1(0.228g,1mmol,1.0eq), 578-3(0.341g,1mmol,1.0eq), Cs were added₂CO₃(0.652g,2mmol,2.0eq)，N₂Adding Pd (dppf) Cl under the condition₂(0.1g,0.1mmol,0.1eq) the reaction was then stirred at 100 ℃ for 12 h, LCMS showed complete reaction, concentrated and purified by column chromatography to give 0.11g (25% yield) of the product as a white solid.

(2) 589(0.44g,1mmol,1.0eq), NBS (0.178g,1mmol,1.0eq) were added to 10ml of DMF and the reaction was stirred at 80 ℃ for 12 h and checked by LCMS to show completion of the reaction and concentrated and purified by column chromatography to give 0.1g (19% yield) (white solid).

20. Synthesis of Compound 596

596-1(0.196g,1mmol,1.0eq), 578-1(0.375g,1mmol,1.0eq), K were added to 10ml of DMF₂CO₃(0.276g,2mmol,2.0eq)，Cu₂O (0.028g,0.2mmol,0.2eq), followed by stirring the reaction at 140 degrees for 2 hours, completion of the reaction was detected by LCMS, the reaction was concentrated and purified by column chromatography to give compound 596(0.1g, 21% yield) (white oil).

Evaluation of biological Activity:

the activity level criteria for plant disruption (i.e. growth control rate) are as follows:

and 5, stage: the growth control rate is more than 85 percent;

4, level: the growth control rate is more than or equal to 60 percent and less than 85 percent;

and 3, level: the growth control rate is more than or equal to 40% and less than 60%;

and 2, stage: the growth control rate is more than or equal to 20% and less than 40%;

level 1: the growth control rate is more than or equal to 5% and less than 20%;

level 0: the growth control rate is less than 5%.

The growth control rate is the fresh weight control rate.

Post-emergence test experiments:

seeds of monocotyledonous and dicotyledonous weed (descurainia sophia, shepherd's purse, Abutilon, Galium aparine, chickweed, Trigonella foenum-graecum, alopecurus, beckia, Slash, candlenus, Veronica, Bromus, Arthrobacter, Phalaris, Amaranthus retroflexus, Chenopodium, Commelina, endive, Convolvulus arvensis, Epimedium spinuloides, Solanum nigrum, Acalyphae, digitaria, Echinochloa crusgalli, Setaria viridis, Euphorbia japonica, Commelina, Arrowia indica, Luciola, Cyperus flaccida, Cyperus rotundus, Setaria heterotypica, Fimbristylis, purslane, Xanthium, Pharbitidis, Oenotherum, etc.) as well as seeds of major crops (wheat, maize, rice, soybean, cotton, rape, millet, sorghum, potato, sesame, castor bean, etc.) are placed in pots, covered with 0.5-2 cm of soil, and sown in a greenhouse, and the plants are treated in a plastic, 2-3-2 weeks, the compound of the invention to be tested is dissolved by acetone, and then tween 80 is added, and 1.5 l/ha missible oil of methyl oleate is used as a synergist, diluted into solution with certain concentration by certain water, and sprayed on plants by a spray tower. The effect of the experiment on weeds was counted after 3 weeks of cultivation in the greenhouse after application, with the compound used in a dose of 500,250,125,60,15,7.5g a.i./ha, repeated three times and the average taken. Representative data are presented in tables 2-3.

TABLE 2 post-emergence weed test

Note: n represents no data.

TABLE 3 post-emergence weed control test

Number of Compounds	Herb of green dog tail	Tang style food	All-grass of Bull's tendon	Herb of Chinese liquor	Indian rorippa herb	Dosage (g a.i./ha)
							3	4	4	4	3	5	7.5
Control Compound A	2	2	3	2	2	7.5
							209	5	5	5	4	5	7.5
Control Compound B	3	2	3	2	2	7.5

Note: control compound a:control compound B:

pre-emergence test experiment:

placing the monocotyledon and dicotyledon weed seeds and main crop seeds (wheat, corn, rice, soybean, cotton, rape, millet and sorghum) in a plastic pot filled with soil, then covering the plastic pot with 0.5-2 cm of soil, respectively dissolving the compound of the invention to be tested by acetone, then adding Tween 80, diluting the solution into solution with a certain concentration by using a certain amount of water, and immediately spraying the solution after sowing. The results of experiments observed after 4 weeks of cultivation in a greenhouse after application show that most of the agents of the invention have superior effects under the measurement of 250g of a.i./ha, especially on weeds such as cockspur grass, crab grass, abutilon and the like, and many of the compounds have good selectivity on corn, wheat, rice and soybean.

Meanwhile, main weed tests in wheat fields and paddy fields show that the compound generally has a good weed control effect, and particularly, the compound has extremely high activity on broadleaf weeds and nutgrass flatsedge which have resistance to ALS inhibitors and are contained in wild arrowheads, Chinese iris, abnormal-shaped nutgrass flatsedge, descurainia sophia, shepherd's purse, maidenhair, cleavers, cyperus rotundus and the like.

Evaluating the safety of transplanted rice and the weed control effect of paddy field:

after the paddy field soil was filled in a tank of 1/1,000,000 hectare, seeds of barnyard grass, japanese iris, and bidens were sown, and soil was lightly covered thereon. Standing in a state of water storage depth of 0.5-1 cm in a greenhouse, and implanting tuber of Pseudobulbus Cremastrae seu pleiones in the next or 2 days. Thereafter, the water storage depth was maintained at 3 to 4 cm, and an aqueous dilution of a wettable powder or a suspension, which was prepared by a usual formulation method, was dropped uniformly by a pipette at a time point when barnyard grass, japanese iris, or burley reached 0.5 leaf and the bulb reached the primary leaf stage to obtain a predetermined amount of active ingredient.

In addition, after filling the 1/1,000,000 hectare pot with paddy field soil, leveling is carried out to ensure that the water storage depth is 3-4 cm, and the rice (japonica rice) at the 3-leaf stage is transplanted with the transplanting depth of 3 cm on the next day. The compound of the present invention was treated on the 5 th day after transplantation in the same manner as described above.

The growth state of cockspur grass, japanese iris, bidens tripartita and edible tulip on day 14 after the treatment with the chemical agent and the growth state of rice on day 21 after the treatment with the chemical agent were respectively observed by naked eyes, and the effects were evaluated on the above activity standard levels, and many compounds showed excellent activity and selectivity.

Note: the barnyard grass, the Chinese iris, the bidens tripartita seeds and the edible tulip are all collected from Heilongjiang in China, and have the drug resistance to pyrazosulfuron-ethyl with the conventional dosage through detection.

Meanwhile, a plurality of tests show that the compound and the composition thereof have good selectivity on gramineous lawns such as zoysia japonica, bermuda grass, festuca arundinacea, bluegrass, ryegrass, seashore paspalum and the like, and can prevent and kill a plurality of key gramineous weeds and broadleaf weeds. Tests on sugarcane, soybean, cotton, sunflower, potato, fruit trees, vegetables and the like under different application modes also show excellent selectivity and commercial value.