Iminoaryl compounds substituted with carboxylic acid derivatives, process for their preparation, herbicidal compositions and uses - Patents.com

Abstract

The present invention relates to the technical field of agrochemicals, in particular to certain iminoaryl compounds substituted with carboxylic acid derivatives, their preparation process, herbicidal compositions and their use. The compounds have the general formula I: [Formula 1] TIFF2023510328000253.tif29170 [wherein, for example, Q is [Case 2] TIFF2023510328000254.tif29170, Y represents halogen, haloalkyl or cyano; Z represents a halogen; M represents CH or N; W represents OX5, SX5 or N(X5)2; X is -CX1X2-(alkyl) n -, -Alkyl-CX1X2-(alkyl) n -or-(CH2) r - represents X3 and X4 each independently represent O, S, NH, or N-alkyl. This compound has excellent herbicidal activity against grass weeds, broadleaf weeds, mint weeds, etc. even at low application rates, and has high selectivity to crops.

Description

[Technical field]

[0001] The present invention relates to the technical field of agrochemicals, in particular to certain iminoaryl compounds substituted with carboxylic acid derivatives, preparation methods, herbicidal compositions and uses thereof. [Background technology]

[0002] Weed control is one of the most important links in the process of achieving high-efficiency agriculture. A variety of herbicides are available on the market. For example, patents WO00 / 50409 and the like describe the use of compounds of the general formula 1-aryl-4-thiotriazine as herbicides, WO95 / 06641 describes compounds of substituted 1-amino-3-phenyluracil with herbicidal activity, and WO95 / 25725 describes compounds of pyrimidinyl aryl ketone oximes with herbicidal and insecticidal activity. However, the herbicidal properties of these known compounds against harmful plants and their selectivity against crops are not entirely satisfactory. And due to challenges such as market expansion, weed resistance, the useful life and economy of pesticides, and people's growing concern about the environment, scientists still need to carry out continuous research and development into new herbicides with high efficacy, safety, economy, and different mechanisms of action. Summary of the Invention

[0003] The present invention relates to the technical field of agricultural chemicals, in particular to a certain type of iminoaryl compound substituted with a carboxylic acid derivative, its preparation method, herbicidal composition and its use. The compound has excellent herbicidal activity against gramineous weeds, broadleaf weeds, cyperaceae weeds, etc. even at low application rates, and has high selectivity against crops. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0004] The technical solutions adopted in the present invention are as follows:

[0005] General formula I': [ka] An iminoaryl compound substituted with a carboxylic acid derivative represented by the formula: Iminoaryl compounds substituted with said carboxylic acid derivatives, where derivative refers to agrochemically suitable derivatives and is used to represent modifications of the carboxylic acid functionality of the present invention, and refers to any ester, acyl hydrazide, imidate, thioimidate, amidine, amide, orthoester, acyl cyanide, acyl halide, thioester, thionoester, dithiolester, nitrile or other carboxylic acid derivatives known in the art.

[0006] Specifically, compounds of general formula I: [ka] The iminoaryl compound is represented by the formula:

[0007] In the above general formulae I' and I, Q is, [ka] represents Y represents halogen, haloalkyl or cyano; Z represents a halogen; M represents CH or N; W represents OX5, SX5 or N(X5)2; X is -CX1X2-(alkyl) n -,-Alkyl-CX1X2-(alkyl) n -or-(CH2) r - represents X1, X2 are each independently H, halogen, cyano, amino, nitro, formyl, cyanoalkyl, hydroxyalkyl, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, alkoxy, alkylthio, alkylamino, haloalkoxy, haloalkylthio, alkylcarbonyl, alkoxycarbonyl, alkoxyalkyl, haloalkoxyalkyl, alkylaminoalkyl, aryl, heterocyclyl, arylalkyl, or heterocyclylalkyl, and X1, X2 are not simultaneously hydrogen, wherein "alkyl", "alkenyl" and "alkynyl" are each independently unsubstituted or substituted with halogen, and "cycloalkyl", "cycloalkylalkyl", "aryl", "heterocyclyl", "arylalkyl" and "heterocyclylalkyl" are each independently unsubstituted or substituted with oxo, halogen, cyano, nitro, alkyl, alkenyl, alkynyl, cycloalkyl, haloalkyl, haloalkenyl, haloalkynyl, halocycloalkyl, cycloalkyl substituted with alkyl, -OR 13 , -SR 13 , -(CO)OR 13 , -(SO2)R 13 , -N(R 13 )2 and -O-alkyl-(CO)OR 13 or two adjacent carbon atoms on the ring are joined together with -OCH2CH2- or -OCH2O- which is unsubstituted or substituted with a halogen to form a fused ring; X3 and X4 each independently represent O, S, NH, or N-alkyl; X5 is H, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, heterocyclyl, aryl, [ka] wherein "alkyl", "alkenyl" and "alkynyl" are each independently unsubstituted or selected from halogen, cyano, nitro, cycloalkyl, cycloalkenyl, heterocyclyl, aryl, [ka] and each of "cycloalkyl", "cycloalkenyl", "heterocyclyl" and "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, -OR 13 , -SR 13 , -(CO)OR 13 , -(SO2)R 13 , -N(R 13 )2 and -O-alkyl-(CO)OR 13 or two adjacent carbon atoms on the ring are joined together with -OCH2CH2- or -OCH2O- which is unsubstituted or substituted with a halogen to form a fused ring; or N(X5)2 is [ka] or an unsubstituted or substituted heterocyclyl having a nitrogen atom at position 1, Q1, Q2, Q3, Q4, and Q5 each independently represent O or S; R1 and R2 each independently represent H, cyano, alkyl, alkenyl, alkynyl, formylalkyl, cyanoalkyl, amino, aminoalkyl, aminocarbonyl, aminocarbonylalkyl, aminosulfonyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl, cycloalkenylalkyl, heterocyclyl, heterocyclylalkyl, aryl, arylalkyl, R4R5N-(CO)-NR3-, [ka] 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 -, R-O-(CO)-alkyl- or R-O-(CO)-O-alkyl-, where "alkyl", "alkenyl" and "alkynyl" are each independently unsubstituted or substituted with halogen, and "amino", "aminoalkyl", "aminocarbonyl", "aminocarbonylalkyl" and "aminosulfonyl" are each independently unsubstituted or substituted with -R 11 , -OR 11 , -(CO)R 11 , -(CO)OR 11 , -alkyl-(CO)OR 11 , -(SO2)R 11 , -(SO2)OR 11 , -alkyl-(SO2)R 11 , -(CO)N(R 12 )2 and -(SO2)N(R 12 )2, and "cycloalkyl", "cycloalkylalkyl", "cycloalkenyl", "cycloalkenylalkyl", "heterocyclyl", "heterocyclylalkyl", "aryl" and "arylalkyl" are each independently unsubstituted or substituted with oxo, halogen, cyano, nitro, alkyl, alkenyl, alkynyl, cycloalkyl, haloalkyl, haloalkenyl, haloalkynyl, halocycloalkyl, alkyl-substituted cycloalkyl, -OR 13 , -SR 13 , -(CO)OR 13 , -(SO2)R 13 , -N(R 13 )2 and -O-alkyl-(CO)OR 13 or two adjacent carbon atoms on the ring are joined together with -OCH2CH2- or -OCH2O- which is unsubstituted or substituted with a halogen to form a fused ring; R6 represents alkyl, alkenyl, alkynyl or cyano, where "alkyl", "alkenyl" and "alkynyl" are each independently unsubstituted or substituted with at least one group selected from halogen, alkoxy and alkoxycarbonyl; R7, R7', R8, and R8' each independently represent H, alkyl, halogen, haloalkyl, amino, hydroxyalkyl, or alkoxy; X 11 are independently H, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl, cycloalkenylalkyl, heterocyclyl, heterocyclylalkyl, aryl, arylalkyl, or [ka] wherein "cycloalkyl", "cycloalkylalkyl", "cycloalkenyl", "cycloalkenylalkyl", "heterocyclyl", "heterocyclylalkyl", "aryl" and "arylalkyl" are each independently unsubstituted or substituted with oxo, halogen, cyano, nitro, alkyl, alkenyl, alkynyl, cycloalkyl, haloalkyl, haloalkenyl, haloalkynyl, halocycloalkyl, alkyl-substituted cycloalkyl, -OR 13 , -SR 13 , -(CO)OR 13 , -(SO2)R 13 , -N(R 13 )2 and -O-alkyl-(CO)OR 13 or two adjacent carbon atoms on the ring are joined together with -OCH2CH2- or -OCH2O- which is unsubstituted or substituted with a halogen to form a fused ring; X 12independently represent alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl, cycloalkenylalkyl, heterocyclyl, heterocyclylalkyl, aryl, or arylalkyl, where "cycloalkyl", "cycloalkylalkyl", "cycloalkenyl", "cycloalkenylalkyl", "heterocyclyl", "heterocyclylalkyl", "aryl" and "arylalkyl" are each independently unsubstituted or substituted with oxo, halogen, cyano, nitro, alkyl, alkenyl, alkynyl, cycloalkyl, haloalkyl, haloalkenyl, haloalkynyl, halocycloalkyl, cycloalkyl substituted with alkyl, -OR 13 , -SR 13 , -(CO)OR 13 , -(SO2)R 13 , -N(R 13 )2 and -O-alkyl-(CO)OR 13 or two adjacent carbon atoms on the ring are joined together with -OCH2CH2- or -OCH2O- which is unsubstituted or substituted with a halogen to form a fused ring; X 13 , X 14 each independently represents H, halogen, cyano, alkoxy, alkoxyalkyl, alkylcarbonyl, alkoxycarbonyl, alkylsulfonyl, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl, cycloalkenylalkyl, aryl, arylalkyl, heterocyclyl or heterocyclylalkyl, or C, X 13 , X 14 are taken together to form an unsubstituted or substituted cyclic structure, or N, X 13 , X 14are taken together to form an unsubstituted or substituted heterocyclyl with a nitrogen atom at position 1, where "alkyl", "alkenyl" and "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 oxo, halogen, cyano, nitro, alkyl, alkenyl, alkynyl, cycloalkyl, haloalkyl, haloalkenyl, haloalkynyl, halocycloalkyl, cycloalkyl substituted with alkyl, -OR 13 , -SR 13 , -(CO)OR 13 , -(SO2)R 13 , -N(R 13 )2 and -O-alkyl-(CO)OR 13 or two adjacent carbon atoms on the ring are joined together with -OCH2CH2- or -OCH2O- which is unsubstituted or substituted with a halogen to form a fused ring; R3, R4, R5 each independently represent H, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl, cycloalkenylalkyl, heterocyclyl, heterocyclylalkyl, aryl, or arylalkyl, where "alkyl", "alkenyl", and "alkynyl" are each independently unsubstituted or substituted with halogen, and "cycloalkyl", "cycloalkylalkyl", "cycloalkenyl", "cycloalkenylalkyl", "heterocyclyl", "heterocyclylalkyl", "aryl" and "arylalkyl" are each independently unsubstituted or substituted with oxo, halogen, cyano, nitro, alkyl, alkenyl, alkynyl, cycloalkyl, haloalkyl, haloalkenyl, haloalkynyl, halocycloalkyl, cycloalkyl substituted with alkyl, -OR 13 , -SR 13 , -(CO)OR 13 , -(SO2)R13 , -N(R 13 )2 and -O-alkyl-(CO)OR 13 or two adjacent carbon atoms on the ring are joined together with -OCH2CH2- or -OCH2O- which is unsubstituted or substituted with a halogen to form a fused ring; R 11 independently represent alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl, cycloalkenylalkyl, phenyl, benzyl, where "alkyl", "alkenyl" and "alkynyl" are each independently unsubstituted or substituted with halogen, and "phenyl" and "benzyl" are each independently unsubstituted or substituted with at least one group selected from halogen, cyano, nitro, alkyl, haloalkyl, alkoxycarbonyl, alkylthio, alkylsulfonyl, alkoxy, and haloalkoxy; R 12 independently represent H, alkyl, alkenyl, alkynyl, alkoxy, alkylsulfonyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl, or cycloalkenylalkyl, or -(CO)N(R 12 )2 or -(SO2)N(R 12 )2 in N(R 12 ) 2 each independently represent an unsubstituted or substituted heterocyclyl having a nitrogen atom at position 1; R 13 represents independently H; alkyl; haloalkyl; phenyl; or phenyl substituted with at least one group selected from halogen, cyano, nitro, alkyl, haloalkyl, alkoxycarbonyl, alkylthio, alkylsulfonyl, alkoxy, and haloalkoxy; r independently represents an integer of 2 or greater; m represents 0, 1 or 2; n independently represents 0 or 1.

[0008] Preferably, Y represents halogen, haloC1-C8 alkyl or cyano; X is -CX1X2-(C1-C8 alkyl) n -, -(C1-C8 alkyl)-CX1X2-(C1-C8 alkyl) n -or-(CH2) r - represents X1 and X2 are each independently H, halogen, cyano, amino, nitro, formyl, cyanoC1-C8 alkyl, hydroxyC1-C8 alkyl, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkylC1-C8 alkyl, C1-C8 alkoxy, C1-C8 alkylthio, C1-C8 alkylamino, haloC1-C8 alkoxy, haloC1-C8 alkylthio, C1-C8 alkylcarbonyl, C1-C8 alkoxycarbonyl, C1-C8 alkoxyC1-C8 alkyl, haloC1-C8 alkoxyC1-C8 alkyl, C1-C8 alkylaminoC1-C8 alkyl, aryl, heterocyclyl, arylC1-C8 alkyl, or heterocyclylC1-C8 alkyl; and 2 is not simultaneously hydrogen, wherein "C1-C8 alkyl", "C2-C8 alkenyl" and "C2-C8 alkynyl" are each independently unsubstituted or substituted with halogen, and "C3-C8 cycloalkyl", "C3-C8 cycloalkylC1-C8 alkyl", "aryl", "heterocyclyl", "arylC1-C8 alkyl" and "heterocyclylC1-C8 alkyl" are each independently unsubstituted or substituted with oxo, halogen, cyano, nitro, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, haloC1-C8 alkyl, haloC2-C8 alkenyl, haloC2-C8 alkynyl, haloC3-C8 cycloalkyl, C3-C8 cycloalkyl substituted with C1-C8 alkyl, -OR 13 , -SR 13 , -(CO)OR 13 , -(SO2)R 13 , -N(R 13 )2 and -O-(C1-C8 alkyl)-(CO)OR 13or two adjacent carbon atoms on the ring are joined together with -OCH2CH2- or -OCH2O- which is unsubstituted or substituted with a halogen to form a fused ring; X3 and X4 each independently represent O, S, NH, or N-(C1-C8)alkyl; X5 is H, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkenyl, heterocyclyl, aryl, [ka] wherein "C1-C8 alkyl", "C2-C8 alkenyl" and "C2-C8 alkynyl" are each independently unsubstituted or selected from halogen, cyano, nitro, C3-C8 cycloalkyl, C3-C8 cycloalkenyl, heterocyclyl, aryl, [ka] and "C3-C8 cycloalkyl", "C3-C8 cycloalkenyl", "heterocyclyl" and "aryl" are each independently unsubstituted or substituted with at least one group selected from oxo, halogen, cyano, nitro, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, haloC1-C8 alkyl, haloC2-C8 alkenyl, haloC2-C8 alkynyl, haloC3-C8 cycloalkyl, C3-C8 cycloalkyl substituted with C1-C8 alkyl, -OR 13 , -SR 13 , -(CO)OR 13 , -(SO2)R 13 , -N(R 13 )2 and -O-(C1-C8 alkyl)-(CO)OR 13 or two adjacent carbon atoms on the ring are joined together with -OCH2CH2- or -OCH2O- which is unsubstituted or substituted with a halogen to form a fused ring; or N(X5)2 is [ka] or a heterocyclyl having a nitrogen atom in position 1, unsubstituted or substituted with at least one group selected from oxo and C1-C8 alkyl: [ka] represents R1 and R2 each independently represent H, cyano, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, formylC1-C8 alkyl, cyanoC1-C8 alkyl, amino, aminoC1-C8 alkyl, aminocarbonyl, aminocarbonylC1-C8 alkyl, aminosulfonyl, C3-C8 cycloalkyl, C3-C8 cycloalkylC1-C8 alkyl, C3-C8 cycloalkenyl, C3-C8 cycloalkenylC1-C8 alkyl, heterocyclyl, heterocyclylC1-C8 alkyl, aryl, arylC1-C8 alkyl, R4R5N-(CO)-NR3-, [ka] 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)-, where "C1-C8 alkyl", "C2-C8 alkenyl", and "C2-C8 alkynyl" are each independently unsubstituted or substituted with halogen, and "amino", "amino C1-C8 alkyl", "aminocarbonyl", "aminocarbonyl C1-C8 alkyl", and "aminosulfonyl" are each independently unsubstituted or substituted with -R 11 , -OR11 , -(CO)R 11 , -(CO)OR 11 , -(C1-C8 alkyl)-(CO)OR 11 , -(SO2)R 11 , -(SO2)OR 11 , -(C1-C8 alkyl)-(SO2)R 11 , -(CO)N(R 12 )2 and -(SO2)N(R 12 )2, wherein "C3-C8 cycloalkyl", "C3-C8 cycloalkylC1-C8 alkyl", "C3-C8 cycloalkenyl", "C3-C8 cycloalkenylC1-C8 alkyl", "heterocyclyl", "heterocyclylC1-C8 alkyl", "aryl" and "arylC1-C8 alkyl" are each independently unsubstituted or substituted with oxo, halogen, cyano, nitro, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, haloC1-C8 alkyl, haloC2-C8 alkenyl, haloC2-C8 alkynyl, haloC3-C8 cycloalkyl, C3-C8 cycloalkyl substituted with C1-C8 alkyl, -OR 13 , -SR 13 , -(CO)OR 13 , -(SO2)R 13 , -N(R 13 )2 and -O-(C1-C8 alkyl)-(CO)OR 13 or two adjacent carbon atoms on the ring are joined together with -OCH2CH2- or -OCH2O- which is unsubstituted or substituted with a halogen to form a fused ring; R6 represents C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl or cyano, where "C1-C8 alkyl", "C2-C8 alkenyl" and "C2-C8 alkynyl" are each independently unsubstituted or substituted with at least one group selected from halogen, C1-C8 alkoxy and C1-C8 alkoxycarbonyl; R7, R7', R8, and R8' each independently represent H, C1-C8 alkyl, halogen, haloC1-C8 alkyl, amino, hydroxyC1-C8 alkyl, or C1-C8 alkoxy; X 11 are independently H, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, haloC1-C8 alkyl, haloC2-C8 alkenyl, haloC2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkylC1-C8 alkyl, C3-C8 cycloalkenyl, C3-C8 cycloalkenylC1-C8 alkyl, heterocyclyl, heterocyclylC1-C8 alkyl, aryl, arylC1-C8 alkyl or [ka] wherein "C3-C8 cycloalkyl", "C3-C8 cycloalkylC1-C8 alkyl", "C3-C8 cycloalkenyl", "C3-C8 cycloalkenylC1-C8 alkyl", "heterocyclyl", "heterocyclylC1-C8 alkyl", "aryl" and "arylC1-C8 alkyl" are each independently unsubstituted or substituted with oxo, halogen, cyano, nitro, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, haloC1-C8 alkyl, haloC2-C8 alkenyl, haloC2-C8 alkynyl, haloC3-C8 cycloalkyl, C3-C8 cycloalkyl substituted with C1-C8 alkyl, -OR 13 , -SR 13 , -(CO)OR 13 , -(SO2)R 13 , -N(R 13 )2 and -O-(C1-C8 alkyl)-(CO)OR 13 or two adjacent carbon atoms on the ring are joined together with -OCH2CH2- or -OCH2O- which is unsubstituted or substituted with a halogen to form a fused ring; X 12independently represent C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, haloC1-C8 alkyl, haloC2-C8 alkenyl, haloC2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkylC1-C8 alkyl, C3-C8 cycloalkenyl, C3-C8 cycloalkenylC1-C8 alkyl, heterocyclyl, heterocyclylC1-C8 alkyl, aryl, or arylC1-C8 alkyl, where "C3-C8 cycloalkyl", "C3-C8 cycloalkylC1-C8 alkyl", "C3-C8 cycloalkenylC1-C8 alkyl" and "C3-C8 cycloalkenylC1-C8 alkyl" are "Alkenyl", "C3-C8 cycloalkenyl C1-C8 alkyl", "heterocyclyl", "heterocyclyl C1-C8 alkyl", "aryl" and "aryl C1-C8 alkyl" are each independently unsubstituted or substituted with oxo, halogen, cyano, nitro, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, haloC1-C8 alkyl, haloC2-C8 alkenyl, haloC2-C8 alkynyl, haloC3-C8 cycloalkyl, C3-C8 cycloalkyl substituted with C1-C8 alkyl, -OR 13 , -SR 13 , -(CO)OR 13 , -(SO2)R 13 , -N(R 13 )2 and -O-(C1-C8 alkyl)-(CO)OR 13 or two adjacent carbon atoms on the ring are joined together with -OCH2CH2- or -OCH2O- which is unsubstituted or substituted with a halogen to form a fused ring; X 13 , X 14each independently represents H, halogen, cyano, C1-C8 alkoxy, C1-C8 alkoxyC1-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 cycloalkylalkyl, C3-C8 cycloalkenyl, C3-C8 cycloalkenylC1-C8 alkyl, aryl, arylC1-C8 alkyl, heterocyclyl or heterocyclylC1-C8 alkyl, or C, X 13 , X 14 together form a 5- to 8-membered carbocyclyl or oxygen-, sulfur- or nitrogen-containing heterocyclyl, or N, X 13 , X 14 are taken together to form a heterocyclyl having a nitrogen atom at position 1, where "C1-C8 alkyl", "C2-C8 alkenyl" and "C2-C8 alkynyl" are each independently unsubstituted or substituted with halogen, and are also included within the scope of the following: "C3-C8 cycloalkyl", "C3-C8 cycloalkylC1-C8 alkyl", "C3-C8 cycloalkenyl", "C3-C8 cycloalkenylC1-C8 alkyl", "aryl", "arylC1 -C8 alkyl", "heterocyclyl" or "heterocyclylC1-C8 alkyl" are each independently unsubstituted or selected from the group consisting of oxo, halogen, cyano, nitro, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, haloC1-C8 alkyl, haloC2-C8 alkenyl, haloC2-C8 alkynyl, haloC3-C8 cycloalkyl, C3-C8 cycloalkyl substituted with C1-C8 alkyl, -OR 13 , -SR 13 , -(CO)OR 13 , -(SO2)R 13 , -N(R 13 )2 and -O-(C1-C8 alkyl)-(CO)OR 13or two adjacent carbon atoms on the ring are joined together with unsubstituted or halogen-substituted -OCH2CH2- or -OCHO- to form a fused ring; the "5-8 membered carbocyclyl or oxygen-, sulfur- or nitrogen-containing heterocyclyl" is unsubstituted or substituted with 1 to 4 groups selected from C1-C8 alkyl, C1-C8 alkoxycarbonyl and benzyl, or is joined together with an aryl or heterocyclyl to form a fused ring; the "heterocyclyl having a nitrogen atom at position 1" is unsubstituted or substituted with at least one group selected from oxo and C1-C8 alkyl; R3, R4, and R5 each independently represent H, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkylC1-C8 alkyl, C3-C8 cycloalkenyl, C3-C8 cycloalkenylC1-C8 alkyl, heterocyclyl, heterocyclylC1-C8 alkyl, aryl, or arylC1-C8 alkyl, where "C1-C8 alkyl", "C2-C8 alkenyl", and "C2-C8 alkynyl" are each independently unsubstituted or substituted with halogen, and "C3-C8 cycloalkyl", "C3-C8 cycloalkenyl" and "C3-C8 alkynyl" are each independently unsubstituted or substituted with halogen, and "C3-C8 cycloalkyl", "C3-C8 cycloalkenyl" and "C3-C8 cycloalken ... "arylC1-C8 alkyl", "C3-C8 cycloalkenyl", "C3-C8 cycloalkenylC1-C8 alkyl", "heterocyclyl", "heterocyclylC1-C8 alkyl", "aryl" and "arylC1-C8 alkyl" are each independently unsubstituted or substituted with oxo, halogen, cyano, nitro, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, haloC1-C8 alkyl, haloC2-C8 alkenyl, haloC2-C8 alkynyl, haloC3-C8 cycloalkyl, C3-C8 cycloalkyl substituted with C1-C8 alkyl, -OR 13 , -SR 13 , -(CO)OR 13 , -(SO2)R 13 , -N(R 13 )2 and -O-(C1-C8 alkyl)-(CO)OR 13or two adjacent carbon atoms on the ring are joined together with -OCH2CH2- or -OCH2O- which is unsubstituted or substituted with a halogen to form a fused ring; R 11 independently represent C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkylC1-C8 alkyl, C3-C8 cycloalkenyl, C3-C8 cycloalkenylC1-C8 alkyl, phenyl, benzyl, where "C1-C8 alkyl", "C2-C8 alkenyl" and "C2-C8 alkynyl" are each independently unsubstituted or substituted with halogen, and "phenyl" and "benzyl" are each independently unsubstituted or substituted with at least one group selected from halogen, cyano, nitro, C1-C8 alkyl, haloC1-C8 alkyl, C1-C8 alkoxycarbonyl, C1-C8 alkylthio, C1-C8 alkylsulfonyl, C1-C8 alkoxy and haloC1-C8 alkoxy; R 12 independently represent H, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C1-C8 alkoxy, C1-C8 alkylsulfonyl, C3-C8 cycloalkyl, C3-C8 cycloalkylC1-C8 alkyl, C3-C8 cycloalkenyl or C3-C8 cycloalkenylC1-C8 alkyl, or -(CO)N(R 12 )2 or -(SO2)N(R 12 )2 in N(R 12 2 is independently a heterocyclyl having a nitrogen atom at position 1, unsubstituted or substituted with at least one group selected from oxo and C1-C8 alkyl: [ka] represents R 13represents independently H; C1-C8 alkyl; haloC1-C8 alkyl; phenyl; or phenyl substituted with at least one group selected from halogen, cyano, nitro, C1-C8 alkyl, haloC1-C8 alkyl, C1-C8 alkoxycarbonyl, C1-C8 alkylthio, C1-C8 alkylsulfonyl, C1-C8 alkoxy and haloC1-C8 alkoxy; r represents 2, 3, 4, 5 or 6.

[0009] More preferably, Y represents halogen, haloC1-C6 alkyl or cyano; X is -CX1X2-(C1-C6 alkyl) n -, -(C1-C6 alkyl)-CX1X2-(C1-C6 alkyl) n -or-(CH2) r - represents X1 and X2 are each independently H, halogen, cyano, amino, nitro, formyl, cyanoC1-C6 alkyl, hydroxyC1-C6 alkyl, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkylC1-C6 alkyl, C1-C6 alkoxy, C1-C6 alkylthio, C1-C6 alkylamino, haloC1-C6 alkoxy, haloC1-C6 alkylthio, C1-C6 alkylcarbonyl, C1-C6 alkoxycarbonyl, C1-C6 alkoxyC1-C6 alkyl, haloC1-C6 alkoxyC1-C6 alkyl, C1-C6 alkylaminoC1-C6 alkyl, aryl, heterocyclyl, arylC1-C6 alkyl, or heterocyclylC1-C6 alkyl; and 2 is not simultaneously hydrogen, wherein "C1-C6 alkyl", "C2-C6 alkenyl" and "C2-C6 alkynyl" are each independently unsubstituted or substituted with halogen, and "C3-C6 cycloalkyl", "C3-C6 cycloalkylC1-C6 alkyl", "aryl", "heterocyclyl", "arylC1-C6 alkyl" and "heterocyclylC1-C6 alkyl" are each independently unsubstituted or substituted with oxo, halogen, cyano, nitro, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, haloC1-C6 alkyl, haloC2-C6 alkenyl, haloC2-C6 alkynyl, haloC3-C6 cycloalkyl, C3-C6 cycloalkyl substituted with C1-C6 alkyl, -OR 13 , -SR 13 , -(CO)OR 13 , -(SO2)R 13 , -N(R 13 )2 and -O-(C1-C6 alkyl)-(CO)OR 13 or two adjacent carbon atoms on the ring are joined together with -OCH2CH2- or -OCH2O- which is unsubstituted or substituted with a halogen to form a fused ring; X3 and X4 each independently represent O, S, NH, or N-(C1-C6)alkyl; X5 is H, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkenyl, heterocyclyl, aryl, [ka] wherein "C1-C6 alkyl", "C2-C6 alkenyl" and "C2-C6 alkynyl" are each independently unsubstituted or selected from halogen, cyano, nitro, C3-C6 cycloalkyl, C3-C6 cycloalkenyl, heterocyclyl, aryl, [ka] and "C3-C6 cycloalkyl", "C3-C6 cycloalkenyl", "heterocyclyl" and "aryl" are each independently unsubstituted or substituted with at least one group selected from oxo, halogen, cyano, nitro, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, haloC1-C6 alkyl, haloC2-C6 alkenyl, haloC2-C6 alkynyl, haloC3-C6 cycloalkyl, C3-C6 cycloalkyl substituted with C1-C6 alkyl, -OR 13 , -SR 13 , -(CO)OR 13 , -(SO2)R 13 , -N(R 13 )2 and -O-(C1-C6 alkyl)-(CO)OR 13 or two adjacent carbon atoms on the ring are joined together with -OCH2CH2- or -OCH2O-, which is unsubstituted or substituted with a halogen, to form a fused ring; or N(X5)2 is [ka] or heterocyclyl unsubstituted or substituted by 1, 2 or 3 groups selected from oxo and C1-C6 alkyl, having a nitrogen atom in position 1: [ka] represents R1 and R2 each independently represent H, cyano, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, formylC1-C6 alkyl, cyanoC1-C6 alkyl, amino, aminoC1-C6 alkyl, aminocarbonyl, aminocarbonylC1-C6 alkyl, aminosulfonyl, C3-C6 cycloalkyl, C3-C6 cycloalkylC1-C6 alkyl, C3-C6 cycloalkenyl, C3-C6 cycloalkenylC1-C6 alkyl, heterocyclyl, heterocyclylC1-C6 alkyl, aryl, arylC1-C6 alkyl, R4R5N-(CO)-NR3-, [ka] 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)-, where "C1-C6 alkyl", "C2-C6 alkenyl", and "C2-C6 alkynyl" are each independently unsubstituted or substituted with halogen, and "amino", "amino C1-C6 alkyl", "aminocarbonyl", "aminocarbonyl C1-C6 alkyl", and "aminosulfonyl" are each independently unsubstituted or substituted with -R 11 , -OR 11 , -(CO)R 11 , -(CO)OR 11 , -(C1-C6 alkyl)-(CO)OR 11 , -(SO2)R 11 , -(SO2)OR 11 , -(C1-C6 alkyl)-(SO2)R 11 , -(CO)N(R12 )2 and -(SO2)N(R 12 )2, and "C3-C6 cycloalkyl", "C3-C6 cycloalkylC1-C6 alkyl", "C3-C6 cycloalkenyl", "C3-C6 cycloalkenylC1-C6 alkyl", "heterocyclyl", "heterocyclylC1-C6 alkyl", "aryl" and "arylC1-C6 alkyl" are each independently unsubstituted or substituted with oxo, halogen, cyano, nitro, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, haloC1-C6 alkyl, haloC2-C6 alkenyl, haloC2-C6 alkynyl, haloC3-C6 cycloalkyl, C3-C6 cycloalkyl substituted with C1-C6 alkyl, -OR 13 , -SR 13 , -(CO)OR 13 , -(SO2)R 13 , -N(R 13 )2 and -O-(C1-C6 alkyl)-(CO)OR 13 or two adjacent carbon atoms on the ring are joined together with -OCH2CH2- or -OCH2O- which is unsubstituted or substituted with a halogen to form a fused ring; R6 represents C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl or cyano, where "C1-C6 alkyl", "C2-C6 alkenyl" and "C2-C6 alkynyl" are each independently unsubstituted or substituted with 1, 2 or 3 groups selected from halogen, C1-C6 alkoxy and C1-C6 alkoxycarbonyl; R7, R7', R8, and R8' each independently represent H, C1-C6 alkyl, halogen, haloC1-C6 alkyl, amino, hydroxyC1-C6 alkyl, or C1-C6 alkoxy; X 11are independently H, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, haloC1-C6 alkyl, haloC2-C6 alkenyl, haloC2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkylC1-C6 alkyl, C3-C6 cycloalkenyl, C3-C6 cycloalkenylC1-C6 alkyl, heterocyclyl, heterocyclylC1-C6 alkyl, aryl, arylC1-C6 alkyl or [ka] wherein "C3-C6 cycloalkyl", "C3-C6 cycloalkylC1-C6 alkyl", "C3-C6 cycloalkenyl", "C3-C6 cycloalkenylC1-C6 alkyl", "heterocyclyl", "heterocyclylC1-C6 alkyl", "aryl" and "arylC1-C6 alkyl" are each independently unsubstituted or substituted with oxo, halogen, cyano, nitro, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, haloC1-C6 alkyl, haloC2-C6 alkenyl, haloC2-C6 alkynyl, haloC3-C6 cycloalkyl, C3-C6 cycloalkyl substituted with C1-C6 alkyl, -OR 13 , -SR 13 , -(CO)OR 13 , -(SO2)R 13 , -N(R 13 )2 and -O-(C1-C6 alkyl)-(CO)OR 13 or two adjacent carbon atoms on the ring are joined together with -OCH2CH2- or -OCH2O- which is unsubstituted or substituted with a halogen to form a fused ring; X 12independently represent C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, halo C1-C6 alkyl, halo C2-C6 alkenyl, halo C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkylC1-C6 alkyl, C3-C6 cycloalkenyl, C3-C6 cycloalkenylC1-C6 alkyl, heterocyclyl, heterocyclylC1-C6 alkyl, aryl or arylC1-C6 alkyl, where "C3-C6 cycloalkyl", "C3-C6 cycloalkylC1-C6 alkyl", "C3-C6 cycloa "C3-C6 cycloalkenyl C1-C6 alkyl", "heterocyclyl", "heterocyclyl C1-C6 alkyl", "aryl" and "aryl C1-C6 alkyl" are each independently unsubstituted or substituted with 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 with C1-C6 alkyl, -OR 13 , -SR 13 , -(CO)OR 13 , -(SO2)R 13 , -N(R 13 )2 and -O-(C1-C6 alkyl)-(CO)OR 13 or two adjacent carbon atoms on the ring are joined together with -OCH2CH2- or -OCH2O- which is unsubstituted or substituted with a halogen to form a fused ring; X 13 , X 14each independently represents H, halogen, cyano, C1-C6 alkoxy, C1-C6 alkoxyC1-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 cycloalkylalkyl, C3-C6 cycloalkenyl, C3-C6 cycloalkenylC1-C6 alkyl, aryl, arylC1-C6 alkyl, heterocyclyl or heterocyclylC1-C6 alkyl, or C, X 13 , X 14 together form a 5- to 8-membered carbocyclyl or oxygen-, sulfur- or nitrogen-containing heterocyclyl, or N, X 13 , X 14 taken together form a heterocyclyl having a nitrogen atom in position 1: [ka] wherein "C1-C6 alkyl", "C2-C6 alkenyl" and "C2-C6 alkynyl" are each independently unsubstituted or substituted with halogen, and "C3-C6 cycloalkyl", "C3-C6 cycloalkylC1-C6 alkyl", "C3-C6 cycloalkenyl", "C3-C6 cycloalkenylC1-C6 alkyl", "aryl", "arylC1-C6 alkyl", "heterocyclyl" or "heterocyclylC1-C6 alkyl" are each independently unsubstituted or substituted with oxo, halogen, cyano, nitro, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, haloC1-C6 alkyl, haloC2-C6 alkenyl, haloC2-C6 alkynyl, haloC3-C6 cycloalkyl, C3-C6 cycloalkyl substituted with C1-C6 alkyl, -OR 13 , -SR 13 , -(CO)OR 13 , -(SO2)R 13 , -N(R 13 )2 and -O-(C1-C6 alkyl)-(CO)OR 13or two adjacent carbon atoms on the ring are joined together with unsubstituted or halogen-substituted -OCH2CH2- or -OCH2O- to form a fused ring; and the "5-8-membered carbocyclyl or oxygen-, sulfur- or nitrogen-containing heterocyclyl" is unsubstituted or substituted with 1, 2 or 3 groups selected from C1-C6 alkyl, C1-C6 alkoxycarbonyl and benzyl, or is joined together with an aryl or heterocyclyl to form a fused ring; [ka] is unsubstituted or substituted with 1, 2 or 3 groups selected from oxo and C1-C6 alkyl; R3, R4, and R5 each independently represent H, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkylC1-C6 alkyl, C3-C6 cycloalkenyl, C3-C6 cycloalkenylC1-C6 alkyl, heterocyclyl, heterocyclylC1-C6 alkyl, aryl, or arylC1-C6 alkyl, where "C1-C6 alkyl", "C2-C6 alkenyl", and "C2-C6 alkynyl" are each independently unsubstituted or substituted with halogen, and "C3-C6 cycloalkyl", "C3-C6 cycloalkenyl" and "C3-C6 alkynyl" are each independently unsubstituted or substituted with halogen, and "C3-C6 cycloalkyl", "C3-C6 cycloalkenyl" and "C3-C6 cycloalken ... "C1-C6 alkyl", "C3-C6 cycloalkenyl", "C3-C6 cycloalkenyl C1-C6 alkyl", "heterocyclyl", "heterocyclyl C1-C6 alkyl", "aryl" and "aryl C1-C6 alkyl" are each independently unsubstituted or substituted with 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 with C1-C6 alkyl, -OR 13 , -SR 13 , -(CO)OR 13 , -(SO2)R 13, -N(R 13 )2 and -O-(C1-C6 alkyl)-(CO)OR 13 or two adjacent carbon atoms on the ring are joined together with -OCH2CH2- or -OCH2O- which is unsubstituted or substituted with a halogen to form a fused ring; R 11 independently represent C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkylC1-C6 alkyl, C3-C6 cycloalkenyl, C3-C6 cycloalkenylC1-C6 alkyl, phenyl, benzyl, where "C1-C6 alkyl", "C2-C6 alkenyl" and "C2-C6 alkynyl" are each independently unsubstituted or substituted with halogen, and "phenyl" and "benzyl" are each independently unsubstituted or substituted with 1, 2 or 3 groups selected from halogen, cyano, nitro, C1-C6 alkyl, haloC1-C6 alkyl, C1-C6 alkoxycarbonyl, C1-C6 alkylthio, C1-C6 alkylsulfonyl, C1-C6 alkoxy and haloC1-C6 alkoxy; R 12 independently represent H, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 alkoxy, C1-C6 alkylsulfonyl, C3-C6 cycloalkyl, C3-C6 cycloalkylC1-C6 alkyl, C3-C6 cycloalkenyl or C3-C6 cycloalkenylC1-C6 alkyl, or -(CO)N(R 12 )2 or -(SO2)N(R 12 )2 in N(R 12 2 independently represents a heterocyclyl having a nitrogen atom at position 1, unsubstituted or substituted with one, two or three groups selected from oxo and C1-C6 alkyl: [ka] represents R 13represents independently H; C1-C6 alkyl; haloC1-C6 alkyl; phenyl; or phenyl substituted by one, two or three groups selected from halogen, cyano, nitro, C1-C6 alkyl, haloC1-C6 alkyl, C1-C6 alkoxycarbonyl, C1-C6 alkylthio, C1-C6 alkylsulfonyl, C1-C6 alkoxy and haloC1-C6 alkoxy.

[0010] Even more preferably, X is -CX1X2-(C1-C3 alkyl) n -, -(C1-C3 alkyl)-CX1X2-(C1-C3 alkyl) n -or-(CH2) r - represents X1 and X2 are each independently H, halogen, cyano, amino, nitro, formyl, cyanoC1-C3 alkyl, hydroxyC1-C3 alkyl, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkylC1-C3 alkyl, C1-C6 alkoxy, C1-C6 alkylthio, C1-C6 alkylamino, haloC1-C6 alkoxy, haloC1-C6 alkylthio, C1-C6 alkylcarbonyl, C1-C6 alkoxycarbonyl, C1-C6 alkoxyC1-C3 alkyl, haloC1-C6 alkoxyC1-C3 alkyl, C1-C6 alkylaminoC1-C3 alkyl, aryl, heterocyclyl, arylC1-C3 alkyl, or heterocyclylC1-C3 alkyl; and 2 is not simultaneously hydrogen, wherein "C1-C6 alkyl", "C2-C6 alkenyl" and "C2-C6 alkynyl" are each independently unsubstituted or substituted with halogen, and "C3-C6 cycloalkyl", "C3-C6 cycloalkylC1-C3 alkyl", "aryl", "heterocyclyl", "arylC1-C3 alkyl" and "heterocyclylC1-C3 alkyl" are each independently unsubstituted or substituted with oxo, halogen, cyano, nitro, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, haloC1-C6 alkyl, haloC2-C6 alkenyl, haloC2-C6 alkynyl, haloC3-C6 cycloalkyl, C3-C6 cycloalkyl substituted with C1-C6 alkyl, -OR 13 , -SR 13 , -(CO)OR 13 , -(SO2)R 13 , -N(R 13 )2 and -O-(C1-C3 alkyl)-(CO)OR 13 or two adjacent carbon atoms on the ring are joined together with -OCH2CH2- or -OCH2O- which is unsubstituted or substituted with a halogen to form a fused ring; X5 is H, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkenyl, heterocyclyl, aryl, [ka] wherein "C1-C6 alkyl", "C2-C6 alkenyl" and "C2-C6 alkynyl" are each independently unsubstituted or selected from halogen, cyano, nitro, C3-C6 cycloalkyl, C3-C6 cycloalkenyl, heterocyclyl, aryl, [ka] and "C3-C6 cycloalkyl", "C3-C6 cycloalkenyl", "heterocyclyl" and "aryl" are each independently unsubstituted or substituted with oxo, halogen, cyano, nitro, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, haloC1-C6 alkyl, haloC2-C6 alkenyl, haloC2-C6 alkynyl, haloC3-C6 cycloalkyl, C3-C6 cycloalkyl substituted with C1-C6 alkyl, -OR 13 , -SR 13 , -(CO)OR 13 , -(SO2)R 13 , -N(R 13 )2 and -O-(C1-C3 alkyl)-(CO)OR 13 or two adjacent carbon atoms on the ring are joined together with -OCH2CH2- or -OCH2O-, which is unsubstituted or substituted with a halogen, to form a fused ring; or N(X5)2 is [ka] or a heterocyclyl having a nitrogen atom at position 1 and unsubstituted or substituted by one, two or three groups selected from oxo and C1-C6 alkyl; [ka] represents X 11 are independently H, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, haloC1-C6 alkyl, haloC2-C6 alkenyl, haloC2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkylC1-C3 alkyl, C3-C6 cycloalkenyl, C3-C6 cycloalkenylC1-C3 alkyl, heterocyclyl, heterocyclylC1-C3 alkyl, aryl, arylC1-C3 alkyl or [ka] wherein "C3-C6 cycloalkyl", "C3-C6 cycloalkylC1-C3 alkyl", "C3-C6 cycloalkenyl", "C3-C6 cycloalkenylC1-C3 alkyl", "heterocyclyl", "heterocyclylC1-C3 alkyl", "aryl" and "arylC1-C3 alkyl" are each independently unsubstituted or substituted with oxo, halogen, cyano, nitro, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, haloC1-C6 alkyl, haloC2-C6 alkenyl, haloC2-C6 alkynyl, haloC3-C6 cycloalkyl, C3-C6 cycloalkyl substituted with C1-C6 alkyl, -OR 13 , -SR 13 , -(CO)OR 13 , -(SO2)R 13 , -N(R 13 )2 and -O-(C1-C3 alkyl)-(CO)OR 13 or two adjacent carbon atoms on the ring are joined together with -OCH2CH2- or -OCH2O- which is unsubstituted or substituted with a halogen to form a fused ring; X 12independently represent C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, halo C1-C6 alkyl, halo C2-C6 alkenyl, halo C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkylC1-C3 alkyl, C3-C6 cycloalkenyl, C3-C6 cycloalkenylC1-C3 alkyl, heterocyclyl, heterocyclylC1-C3 alkyl, aryl or arylC1-C3 alkyl, where "C3-C6 cycloalkyl", "C3-C6 cycloalkylC1-C3 alkyl", "C3-C6 cycloalkenylC1-C3 alkyl" and "C3-C6 cycloalkenylC1-C3 alkyl" are used. "C3-C6 cycloalkenyl C1-C3 alkyl", "heterocyclyl", "heterocyclyl C1-C3 alkyl", "aryl" and "aryl C1-C3 alkyl" are each independently unsubstituted or substituted with 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 with C1-C6 alkyl, -OR 13 , -SR 13 , -(CO)OR 13 , -(SO2)R 13 , -N(R 13 )2 and -O-(C1-C3 alkyl)-(CO)OR 13 or two adjacent carbon atoms on the ring are joined together with -OCH2CH2- or -OCH2O- which is unsubstituted or substituted with a halogen to form a fused ring; X 13 , X 14each independently represents H, halogen, cyano, C1-C6 alkoxy, C1-C6 alkoxyC1-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 cycloalkylalkyl, C3-C6 cycloalkenyl, C3-C6 cycloalkenylC1-C3 alkyl, aryl, arylC1-C3 alkyl, heterocyclyl or heterocyclylC1-C3 alkyl, or C, X 13 , X 14 together form a 5- to 8-membered, saturated carbocyclyl, [ka] or N, X 13 , X 14 taken together form a heterocyclyl having a nitrogen atom in position 1: [ka] wherein "C1-C6 alkyl", "C2-C6 alkenyl" and "C2-C6 alkynyl" are each independently unsubstituted or substituted with halogen, and "C3-C6 cycloalkyl", "C3-C6 cycloalkylC1-C3 alkyl", "C3-C6 cycloalkenyl", "C3-C6 cycloalkenylC1-C3 alkyl", "aryl", "arylC1-C3 alkyl", "heterocyclyl" or "heterocyclylC1-C3 alkyl" are each independently unsubstituted or substituted with oxo, halogen, cyano, nitro, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, haloC1-C6 alkyl, haloC2-C6 alkenyl, haloC2-C6 alkynyl, haloC3-C6 cycloalkyl, C3-C6 cycloalkyl substituted with C1-C6 alkyl, -OR 13 , -SR 13 , -(CO)OR 13 , -(SO2)R 13 , -N(R 13)2 and -O-(C1-C3 alkyl)-(CO)OR 13 or two adjacent carbon atoms on the ring are joined to an unsubstituted or halogen-substituted -OCH2CH2- or -OCH2O- to form a fused ring, and "5- to 8-membered saturated carbocyclyl, [ka] is unsubstituted or substituted with 1, 2 or 3 groups selected from C1-C6 alkyl, C1-C6 alkoxycarbonyl and benzyl, or forms a fused ring together with phenyl or thienyl; [ka] is unsubstituted or substituted with 1, 2 or 3 groups selected from oxo and C1-C6 alkyl.

[0011] More preferably, Q is, [ka] Represents.

[0012] In the definition of the compounds represented by the formula above and all structural formulae below, the terminology used, whether used alone or in a compound word, represents the following substituents: An alkyl having three or more carbon atoms may be linear or branched. For example, the compound word "-alkyl-(CO)OR 11 The alkyl in " may be -CH2-, -CH2CH2-, -CH(CH3)-, -CH2CH2CH2-, -C(CH3)2-, etc., and "-C(CH2) r"-" may be -CH2CH2-, -CH2CH2CH2-, etc. Alkyl is, for example, C1 alkyl: methyl; C2 alkyl: ethyl; C3 alkyl: propyl, e.g., n-propyl or isopropyl; C4 alkyl: butyl, e.g., n-butyl, isobutyl, tert-butyl or 2-butyl; C5 alkyl: pentyl, e.g., n-pentyl; C6 alkyl: hexyl, e.g., n-hexyl, isohexyl or 1,3-dimethylbutyl. Similarly, alkenyl is, for example, vinyl, allyl, 1-methylprop-2-en-1-yl, 2-methylprop-2-en-1-yl, but-2-en-1-yl, butyl-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 and 1-methylbut-3-yn-1-yl. The multiple bond may be located at any position of each unsaturated group. Cycloalkyl is, for example, a carbocyclic saturated ring system having 3 to 6 carbon atoms, such as cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl. Similarly, cycloalkenyl is, for example, a monocyclic alkenyl having 3 to 6 carbon ring members, such as cyclopropenyl, cyclobutenyl, cyclopentenyl and cyclohexenyl, where the double bond may be located at any position. Halogen is fluorine, chlorine, bromine or iodine.

[0013] Unless otherwise specified, "aryl" in the present invention includes the following groups: phenyl, naphthyl, [ka] "Heterocyclyl" includes not only saturated or unsaturated non-aromatic cyclic groups, but also "heteroaryl", which are saturated or unsaturated non-aromatic cyclic groups such as the following groups: [ka] "Heteroaryl" includes, but is not limited to, aromatic cyclic groups having 3-6 ring atoms, optionally fused to a benzo ring, in which one to four (e.g., one, two, three, or four) heteroatoms in the ring are selected from the group consisting of oxygen, nitrogen, and sulfur. For example, [ka] It is.

[0014] It should be understood that when a group is substituted by a group, it means that the group is substituted by one or more of the same or different groups selected from the above groups. Moreover, the same or different substitution characters contained in the same or different substituents are each independently selected and may be the same or different. This also applies to ring systems formed by different atoms and units. On the other hand, the claims exclude compounds that are chemically unstable under standard conditions known to those skilled in the art.

[0015] In addition, unless otherwise defined, the terms preceding or following juxtaposed substituents (separated by "," or "or") in the present invention have a limiting effect on each substituent, for example, the term "unsubstituted or halogen-substituted" in the phrase "-OCH2CH2- or -OCHO-, unsubstituted or halogen-substituted" has a limiting effect on each of the subsequent groups "-OCH2CH2-" and "-OCHO-"; "alkylamino" refers to an amino group mono- or di-substituted with alkyl, and other substituted amino groups are similarly defined; groups with no specified binding site (including heterocyclyl, aryl, etc.) can be bound at any site (including C or N site); if substituted, the substituent can be substituted at any site as long as it follows the valence bond theory. For example, heteroaryl [ka] When is substituted with one methyl, it is [ka] etc.

[0016] In the general formula I, the carbon atom (C * It should be noted that when X1 and X2 are chiral centers (i.e., when X1 and X2 are not identical), they have the R or S configuration, preferably the R configuration, and the stereochemical purity is 60-100% (R), preferably 70-100% (R), more preferably 80-100% (R), even more preferably 90-100% (R), and even more preferably 95-100% (R), based on the content of stereoisomers having the R and S configurations at this position. Here, "stereochemical purity" means the amount of the stated stereoisomer expressed as a percentage of the total amount of stereoisomers having a given chiral center.

[0017] In the present invention, the marked compound of formula I * The stereochemical configuration at position is determined to be predominantly (R) according to the Cahn-Ingold-Prelog system. However, the subject of the present invention also relates to all stereoisomers at other positions encompassed by formula I and their mixtures. Such compounds of formula I contain, for example, one or more additional asymmetric carbon atoms or other double bonds not specifically depicted in formula I. It is understood that the present invention encompasses both the pure isomers and their more or less enriched mixtures. Here, the marked * The asymmetric carbon atom at the position is in the R-configuration or, in a mixture, one or more compounds of the same chemical constitution may be in the marked * Although compounds having the R-configuration at the marked positions are present predominantly (at least 60% R-configuration), other asymmetric carbon atoms may also be present in racemic form or more or less resolved. *When the requirements of stereochemical configuration at a position are met, the possible stereoisomers defined by their specific spatial configuration, e.g., enantiomers, diastereomers, Z- and E-isomers, are all included in formula I. They can be obtained by conventional methods from mixtures of stereoisomers or can be prepared by stereoselective reactions in combination with the use of stereochemically pure starting materials.

[0018] The invention also encompasses any keto and enol tautomeric forms as well as mixtures and salts thereof, when the respective functional groups are present.

[0019] Stereoisomers can be obtained by optical resolution from the mixture obtained in the preparation. Stereoisomers can also be selectively prepared by using stereoselective reactions and by using optically active raw materials and / or auxiliary agents. Usually, conventional methods for optical resolution (see Textbooks of Stereochemistry) can be used, such as the following methods for separating mixtures into diastereomers, such as physical methods, such as crystallization, chromatography (particularly column chromatography and high pressure liquid chromatography), distillation (distillation under reduced pressure if necessary), extraction and other methods. In general, it is possible to separate the remaining mixture of enantiomers by chromatographic separation on a chiral solid phase. A method suitable for use on a preparative or industrial scale is, for example, the crystallization of diastereomeric salts, which can be obtained, if appropriate, from compound (I) using optically active acids and, if acidic groups are present, from compounds using optically active bases.

[0020] A method for preparing an iminoaryl compound substituted with a carboxylic acid derivative, comprising the steps of: The compound represented by the general formula II and the compound represented by the general formula III' are subjected to an elimination reaction, and the reaction is carried out according to the following chemical reaction formula: [ka] or obtaining a compound of general formula I' by The compound represented by the general formula II and the compound represented by the general formula III are subjected to an elimination reaction, and the reaction is carried out according to the following chemical reaction formula: [ka] obtaining a compound of general formula I by Including, in which Hal represents halogen and the other substituents Q, M, W, Y, Z, X, X3 and X4 are as defined above, Preferably, the process is provided wherein the reaction is carried out in the presence of a base and a solvent.

[0021] The base is at least one selected from inorganic bases (e.g., K2CO3, Na2CO3, Cs2CO3, NaHCO3, KF, CsF, KOAc, AcONa, K3PO4, t-BuONa, EtONa, NaOH, KOH, NaOMe, etc.) and organic bases (e.g., pyrazole, triethylamine, DIEA, etc.).

[0022] The solvent is at least one selected from DMF, methanol, ethanol, acetonitrile, dichloroethane, DMSO, dioxane, dichloromethane, and ethyl acetate.

[0023] In addition, Q [ka] When the formula is represented by the formula: [ka] The target compound can also be prepared by preparing the compound shown below and then carrying out a conventional substitution reaction with R6-Hal (Hal represents halogen, and R6 represents alkyl, alkenyl, alkynyl, or haloalkyl).

[0024] The present invention also provides a herbicidal composition comprising (i) a herbicidally effective amount of at least one iminoaryl compound substituted with a carboxylic acid derivative (component A), (ii) preferably further comprising a herbicidally effective amount of another herbicide (component B) and / or one or more safeners, and (iii) more preferably further comprising an agriculturally acceptable formulation adjuvant.

[0025] In a specific embodiment, the following compound: (1) Topramezone (CAS NO.: 210631-68-8), isoxaflutole (CAS NO.: 141112-29-0), tembotrione (CAS NO.: 335104-84-2), teflurtrione (CAS NO.: 473278-76-1), bipyrazone (CAS NO.: 1622908-18-2), ciprolafluone (CAS NO.: 1855929-45-1), tripyrasulfone (CAS NO.: 1911613-97-2), fenpyrazone (CAS NO.: 1992017-55-6) and [ka] an HPPD inhibitor selected from: (2) PDS inhibitors selected from flurtamone (CAS NO.: 96525-23-4), diflufenican (CAS NO.: 83164-33-4) and picolinafen (CAS NO.: 137641-05-5); (3) DOXP inhibitors selected from clomazone (CAS NO.: 81777-89-1) and bixlozone (CAS NO.: 81777-95-9); (4) ALS inhibitors selected from tribenuron methyl (CAS NO.: 101200-48-0), thifensulfuron methyl (CAS NO.: 79277-27-3), pyrazosulfuron ethyl (CAS NO.: 93697-74-6), thiencarbazone methyl (CAS NO.: 317815-83-1), halosulfuron methyl (CAS NO.: 100784-20-1), rimsulfuron (CAS NO.: 122931-48-0), nicosulfuron (CAS NO.: 111991-09-4) and imazamox (CAS NO.: 114311-32-9); (5) ACCase inhibitors selected from clethodim (CAS NO.: 99129-21-2), sethoxydim (CAS NO.: 74051-80-2) and quizalofop-p-methyl (CAS NO.: 100646-51-3); (6) PPO inhibitors selected from oxyfluorfen (CAS NO.: 42874-03-3), oxadiazon (CAS NO.: 19666-30-9), oxadiargyl (CAS NO.: 39807-15-3), sulfentrazone (CAS NO.: 122836-35-5), pyraclonil (CAS NO.: 158353-15-2), flumioxazin (CAS NO.: 103361-09-7), saflufenacil (CAS NO.: 372137-35-4), carfentrazone-ethyl (CAS NO.: 128639-02-1) and trifludimoxadine (CAS NO.: 1258836-72-4); (7) PSII inhibitors selected from metribuzin (CAS NO.: 21087-64-9), terbuthylazine (CAS NO.: 5915-41-3), amicarbazone (CAS NO.: 129909-90-6), chlortoluron (CAS NO.: 15545-48-9), isoproturon (CAS NO.: 34123-59-6), bromacil (CAS NO.: 314-40-9), propanil (CAS NO.: 709-98-8), desmedipham (CAS NO.: 13684-56-5), phenmedipham (CAS NO.: 13684-63-4), bentazon (CAS NO.: 25057-89-0) and bromoxynil (CAS NO.: 1689-84-5); (8) a microtubule polymerization inhibitor selected from butruarin (CAS NO.: 33629-47-9) and pendimethalin (CAS NO.: 40487-42-1); (9) VLCFA inhibitors selected from butachlor (CAS NO.: 23184-66-9), pretilachlor (CAS NO.: 51218-49-6), mefenacet (CAS NO.: 73250-68-7), s-metolachlor (CAS NO.: 87392-12-9), flufenacet (CAS NO.: 142459-58-3), pyroxasulfone (CAS NO.: 447399-55-5) and anilofos (CAS NO.: 764249-01-0); (10) Lipid synthesis (non-acetyl-CoA carboxylase) inhibitors: prosulfocarb (CAS NO.: 52888-80-9); (11) [ka] synthetic hormone inhibitors selected from fluroxypyr (CAS NO.: 69377-81-7), florpyrauxifen benzyl (CAS NO.: 1390661-72-9), halauxifen methyl (CAS NO.: 943831-98-9), triclopyr (CAS NO.: 55335-06-3), clopyralid (CAS NO.: 1702-17-6), picloram (CAS NO.: 1918-02-1), aminopyralid (CAS NO.: 150114-71-9), dicamba (CAS NO.: 1918-00-9), 2-methyl-4-chlorophenoxyacetic acid (CAS NO.: 94-74-6) and 2,4-dichlorophenoxyacetic acid (CAS NO.: 94-75-7); (12) EPSPS inhibitor: glyphosate (CAS NO.: 1071-83-6); (13) GS inhibitors selected from glufosinate ammonium (CAS NO.: 77182-82-2) and glufosinate-P-ammonium (CAS NO.: 35597-44-5); (14) PSI inhibitors selected from paraquat dichloride (CAS NO.: 1910-42-5) and diquat dibromide monohydrate (CAS NO.: 2764-72-9); (15) Cellulose synthesis inhibitors selected from triaziflam (CAS NO.: 131475-57-5) and indaziflam (CAS NO.: 950782-86-2); (16) Others: Cinmethylin (CAS NO.: 87818-31-3) and one or more selected from the group consisting of acids, salts and esters thereof.

[0026] In the context of this specification, when the abbreviation of the generic name of an active compound is used, it in each case includes all conventional derivatives, such as esters and salts, and isomers (especially optical isomers), in particular one or more commercially available forms.When the generic name indicates an ester or salt, it also in each case includes all other conventional derivatives, such as other esters, salts, free acids and neutral compounds, and isomers (especially optical isomers), in particular one or more commercially available forms.The chemical name given to a compound means at least one compound that is included in the generic name, and usually means a preferred compound.In the case of sulfonamides (e.g. sulfonylureas), the salts also include the salts formed by exchanging the hydrogen atom in the sulfonamide group with a cation.

[0027] Here, the weight ratio of the active ingredient A to the active ingredient B in the herbicide composition is 1:1000-1000:1, 1:800-800:1 or 1:600-600:1, preferably 1:500-500:1, 1:400-400:1 or 1:300-300:1, more preferably 1:200-200:1, 1:100-100:1 or 1:80-80:1, even more preferably 1:50-50:1, 1:30-30:1, 1:20-20:1, 1:10-10:1, 1:5-1:1 or 1:5-1:1. In some embodiments, the active ingredients A and B together account for 1-95%, preferably 10-80%, of the total weight of the herbicide composition.

[0028] The safener is selected from one or more of isoxadifen-ethyl (CAS: 163520-33-0), cyprosfamide (CAS: 221667-31-8), mefenpyrdiethyl (CAS: 135590-91-9), cloquintocet-mexyl (CAS: 99607-70-2), gibberellic acid (CAS: 77-06-5), furilazol (CAS: 121776-33-8) and metcamifen (CAS: 129531-12-0).

[0029] The formulation auxiliaries include, for example, carriers and / or surfactants.

[0030] As used herein, the term "carrier" refers to an organic or inorganic, natural or synthetic material that facilitates the application of the active ingredient. In general, the carrier must be inert and agriculturally acceptable, particularly to the plant to be treated. The carrier can be a solid, such as clays, natural or synthetic silicates, silicas, resins, waxes, solid fertilizers, etc.; or a liquid, such as water, alcohols, ketones, petroleum fractions, aromatic or paraffinic hydrocarbons, chlorinated hydrocarbons, liquefied gases, etc.

[0031] The surfactants may be ionic or non-ionic and may include emulsifiers, dispersants or wetting agents. Examples that may be mentioned are salts of polyacrylic acid, salts of lignosulfonic acid, salts of phenolsulfonic acid or naphthalenesulfonic acid, polymers of ethylene oxide with aliphatic alcohols or aliphatic acids or aliphatic amines or substituted phenols (especially alkylphenols or arylphenols), sulfosuccinates, taurine derivatives (especially alkyl taurates), phosphoric esters of alcohols or polyhydroxyethylated phenols, alkylsulfonates, alkylarylsulfonates, alkyl sulfates, lauryl ether sulfates, fatty alcohol sulfates, and sulfated hexadecanol, heptadecanol and octadecanol, sulfated fatty alcohol polyglycol ethers, and also condensates of naphthalene or naphthalenesulfonic acid with phenol and formaldehyde, polyoxyethylene octyl phenols, and polyoxyethylene octyl phenols. nyl ethers;ethoxylated isooctylphenol;octylphenol or nonylphenol;polyethylene glycol alkylphenyl ethers;polyethylene glycol tributylphenyl ether;polyethylene glycol tristearyl phenyl ether;alkylaryl polyether alcohols;alcohol-fatty alcohol / ethylene oxide condensates;ethoxylated castor oil;polyoxyethylene alkyl ethers;ethoxylated polyoxypropylene;lauryl alcohol polyglycol ether acetals;sorbitol esters;lignin sulfite waste liquor;proteins;modified proteins;polysaccharides (e.g., methylcellulose);hydrophobically modified starch;polyvinyl alcohols;polycarboxylates;polyalkoxylates;polyvinylamines;polyvinylpyrrolidone;and copolymers thereof. At least one surfactant may be required to facilitate dispersion of the active ingredient in water and proper application to the plant.

[0032] The composition may also include a variety of other ingredients, such as protective colloids, adhesives, thickeners, thixotropic agents, penetrants, stabilizers, chelating agents, dyes, colorants, or polymers.

[0033] The composition of the present invention may be diluted by the user before use or may be used immediately. The composition may be prepared by conventional processing methods, i.e., by mixing the active ingredient(s) with a liquid solvent or solid carrier, and then adding one or more surfactants, such as dispersants, stabilizers, wetting agents, adhesives, defoamers, etc.

[0034] The herbicidal composition may be in a formulation selected from dispersible oil suspensions, aqueous suspensions, suspoemulsions, wettable powders, emulsifiable concentrates, water-dispersible granules (dry suspension concentrates), aqueous emulsions and microemulsions.

[0035] In short, the composition of the present invention can be mixed with solid and liquid additives conventionally used in prior art formulations. If the external conditions change, the amount of active ingredient used will also be different. The external conditions are, for example, temperature, humidity, the nature of the herbicide used, etc. The amount of active ingredient used may vary widely, for example, from 0.001 to 1.0 kg / ha or more, preferably from 0.005 to 750 g / ha, in particular from 0.005 to 500 g / ha.

[0036] Methods for controlling undesirable vegetation are provided which comprise applying a herbicidally effective amount of at least one iminoaryl compound substituted with a carboxylic acid derivative or a herbicidal composition to a plant or to a region thereof or to the soil or water to control the emergence or growth of the undesirable vegetation.

[0037] Provided is the use of at least one iminoaryl compound substituted with a carboxylic acid derivative or a herbicidal composition for controlling undesirable plants, preferably wherein the iminoaryl compound substituted with a carboxylic acid derivative is used to control weeds in useful crops, said useful crops being genetically modified crops or crops treated with gene editing technology.

[0038] The compounds of formula I according to the present invention have a remarkable herbicidal activity against a wide range of economically important monocotyledonous and dicotyledonous harmful plants (undesirable plants).The active compounds also act effectively against perennial weeds that sprout from rhizomes, rootstocks or other perennial organs and are difficult to control.In this context, it is generally unimportant whether the substance is applied before sowing, before emergence or after emergence.Specifically, some representative examples of monocotyledonous and dicotyledonous weeds that can be controlled by the compounds according to the present invention can be mentioned, but these are not limited to specific species. Examples of weed species on which the active compounds act effectively are monocotyledonous Avena species, Lolium species, Alopecurus species, Phalaris species, Echinochloa species, Digitaria species, Setaria species, annual Cyperus species, and perennial Agropyron species, Cynodon species, Imperata species, Sorghum species, and perennial Cyperus species.

[0039] In the case of dicotyledonous weed species, the range of effectiveness extends, for example, from annuals to Galium spp., Viola spp., Veronica spp., Lamium spp., Stellaria spp., Amaranthus spp., Sinapis spp., Ipomoea spp., Sida spp., Matricaria spp. and Abutilon spp., and in the case of perennial weeds to Convolvulus spp., Cirsium spp., Rumex spp. and Artemisia spp. The active compounds according to the invention also achieve a significant control of harmful plants occurring under the specific conditions of rice cultivation, such as Echinochloa, Sagittaria, Alisma, Eleocharis, Scirpus and Cyperus. When the compounds according to the invention are applied to the soil surface pre-emergence, the emergence of weed seedlings is completely prevented or the weeds grow until they reach the cotyledon stage, after which they cease to grow and gradually die completely after 3-4 weeks. In particular, the compounds according to the invention exhibit excellent activity against Apera spica venti, Chenopodium album, Lamium purpureum, Polygonum convulvulus, Stellaria media, Veronica hederifolia, Veronica persica, Viola tricolor, as well as against Amaranthus spp., Cleaver spp. and Kochia spp.

[0040] Undesirable plants also include herbicide resistant or tolerant weed species.

[0041] The compounds according to the present invention have excellent herbicidal effect on monocotyledonous and dicotyledonous weeds, but economically important crops such as wheat, barley, rye, rice, corn, sugar beet, cotton and soybean are not damaged at all or the damage is negligible.In particular, they have excellent compatibility with cereals such as wheat, barley, corn, especially wheat.For these reasons, the compounds are very suitable for selectively controlling undesirable plant growth in planting for agricultural use or planting for ornamental plants.

[0042] Due to their herbicidal properties, these active compounds may be used to control harmful plants in crops of known or yet to be developed transgenic plants. Transgenic plants generally have particularly significant properties, such as resistance to certain insecticides, in particular resistance to certain herbicides, resistance to plant diseases or causative organisms of plant diseases (e.g. certain insects or microorganisms, such as fungi, bacteria or viruses). Other special properties relate, for example, to the quantity, quality, storage stability, composition and specific components of the harvested product. Thus, transgenic plants with increased starch content, transgenic plants with altered starch quality or transgenic plants with different fatty acid compositions in the harvested product are known.

[0043] The use of the compounds of formula I according to the invention or their salts in economically important transgenic crops of useful plants and ornamental plants is preferred, for example crops of cereals such as wheat, barley, rye, oats, millet, rice, cassava, maize, or crops of sugar beet, cotton, soybean, rapeseed, potato, tomato, bean and other vegetable species. The compounds of formula I can be used as herbicides in crops of useful plants which are preferably resistant to the phytotoxicity of herbicides or to which resistance has been conferred by genetic engineering.

[0044] Conventional methods for producing new plants with modified properties compared to known plants include, for example, traditional breeding methods and the generation of mutants. Alternatively, new plants with modified properties can be generated using genetic engineering methods (see, for example, EP-A0221044, EP-A0131624). For example, some examples are: · genetic engineering changes in crop plants to modify the starch synthesized in the plants (e.g. WO92 / 11376, WO92 / 14827, WO91 / 19806); transgenic crops which are resistant to certain herbicides of the glufosinate type (see, for example, EP-A0242236, EP-A0242246), glyphosate type (WO92 / 00377) or sulfonylurea type (EP-A0257993, US Pat. No. 5,013,659A); · transgenic crops with the ability to produce Bacillus thuringiensis toxins (Bt toxins) that confer resistance to certain pests on the plant, e.g. cotton (EP-A0142924, EP-A0193259); Transgenic crops with altered fatty acid composition have been described (WO91 / 13972).

[0045] Numerous molecular biology techniques are basically known that allow the creation of new transgenic plants with modified properties; see, for example, Sambrook et al., 1989, Molecular Cloning, A Laboratory Manual, 2nd ed. Cold Spring Harbor Laboratory Press, Cold Spring Harbor, NY; or Winnacker "Gene und Klone" [Genes and Clones], VCH Weinheim, 2nd edition 1996, or Christou, "Trends in Plant Science" 1 (1996) 423-431). To carry out such genetic engineering procedures, it is possible to introduce nucleic acid molecules into plasmids, which allow the recombination of DNA sequences to cause mutations or changes in the sequence. Using the standard methods mentioned above, it is possible, for example, to replace bases to remove partial sequences or to add natural or synthetic sequences. To connect DNA fragments to each other, adapters or linkers can be attached to the fragments.

[0046] Plant cells with reduced activity of a gene product can be generated, for example, by expressing at least one suitable antisense RNA, sense RNA to achieve a co-suppression effect, or by expressing at least one appropriately constructed ribozyme that specifically cleaves the transcript of the above-mentioned gene product.

[0047] For this purpose, it is possible to use both DNA molecules that contain the entire coding sequence of the gene product, including any flanking sequences that may be present, and DNA molecules that contain only parts of the coding sequence (these parts must be long enough to cause an antisense effect in the cell).It is also possible to use DNA sequences that are highly homologous to the coding sequence of the gene product, but are not completely identical.

[0048] When expressing nucleic acid molecule in plant, synthesized protein can be localized in any desired compartment of plant cell.However, to achieve localization in a specific compartment, it is possible, for example, to combine coding region with DNA sequence that ensures localization in a specific compartment.Such 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).

[0049] The transgenic plant cells can be regenerated into whole plants using known techniques. In principle, the transgenic plants can be of any desired plant species, i.e. both monocotyledonous and dicotyledonous plants. In this way, transgenic plants can be obtained whose properties are modified by overexpression, suppression or inhibition of a homologous (=natural) gene or gene sequence or by expression of a heterologous (=foreign) gene or gene sequence.

[0050] When the active compounds according to the invention are used in transgenic crops, in addition to the effects on harmful plants that can be observed in other crops, there are many effects specific to the application to each transgenic crop.For example, the range of weeds that can be controlled is changed or significantly expanded, the application rate that can be used for application is improved, the favorable good combination performance with the herbicide that transgenic crops are resistant to, and the growth and yield of transgenic crops.Therefore, the present invention also provides the use of the compounds according to the invention as herbicides to control harmful plants in transgenic crops.

[0051] Furthermore, the substances according to the invention have remarkable growth-regulating properties in crops.They are involved in the regulation of plant metabolism, which can be used for targeted control of plant constituents and for accelerating harvest, for example by causing drying and stunted growth.Moreover, they are suitable for generally regulating and suppressing undesirable plant growth, without destroying the plant in the process.The suppression of plant growth plays an important role in monocotyledonous and dicotyledonous crops, because it can reduce or completely prevent lodging.

[0052] The compounds according to the invention can be applied in conventional formulations in the form of wettable powders, emulsifiable concentrates, sprayable solutions, dusts or granules.Therefore, the present invention also provides herbicidal compositions comprising the compounds of formula I.The compounds of formula I can be formulated by various methods, depending on the prevailing biological and / or physicochemical parameters. Examples of suitable formulation options are wettable powders (WP), water-soluble powders (SP), water-soluble concentrates, emulsifiable concentrates (EC), emulsions (EW) (e.g. oil-in-water emulsions and water-in-oil emulsions), sprayable solutions, suspension concentrates (SC), oil dispersions (OD), oil-based or aqueous dispersions, oil-miscible solutions, dusts (DP), capsule suspension concentrates (CS), seed dressing compositions, granules for dusting and for soil application, granules for disintegration of microgranules (GR), spray granules, dressing granules and adsorbent granules, water-dispersible granules (WG), water-soluble granules (SG), ULV formulations, microcapsules and waxes. These individual formulation types are known and are described, for example, in Winnacker-Kuchler, "Chemische Technologie" [Chemical Technology], Volume 7, C. Hauser Verlag Munich, 4th. Edition 1986; Wade van Valkenburg, "Pesticide Formulations", Marcel Dekker, NY, 1973; K. Martens, "Spray Drying" Handbook, 3rd Ed. 1979, G. Goodwin Ltd. London.

[0053] Necessary formulation auxiliaries, such as inert materials, surfactants, solvents and other additives, are likewise known and are described, for example, in Watkins, "Handbook of Insecticide Dust Diluents and Carriers", 2nd Ed., Darland Books, Caldwell NJ, H. v. Olphen, "Introduction to Clay Colloid Chemistry"; 2nd Ed., J. Wiley & Sons, NY; C. Marsden, "Solvents Guide"; 2nd Ed., Interscience, NY 1963; McCutcheon's "Detergents and Emulsifiers Annual", MC Publ. Corp., Ridgewood NJ; Sisley and Wood, "Encyclopedia of Surface Active Agents", Chem. Publ. Co. Inc., NY 1964; Schonfeldt, "Grenzflchenaktive thylenoxidaddukte" [Surface-active ethylene oxide adducts], Wiss. Verlagsgesell., Stuttgart 1976; Winnacker-Kuchler, "Chemische Technologie" [Chemical Technology], Volume 7, C. Hauser Verlag Munich, 4th Edition 1986.

[0054] Wettable powders are formulations which are homogeneously dispersible in water and contain, in addition to the active compounds and diluents or inert substances, surfactants of the ionic and / or nonionic type (wetting agents, dispersants), such as polyethoxylated alkylphenols, polyethoxylated fatty alcohols, polyethoxylated fatty amines, fatty alcohol polyglycol ether sulfates, alkanesulfonates, alkylbenzenesulfonates, sodium ligninsulfonate, sodium 2,2'-dinaphthylmethane-6,6'-disulfonate, sodium dibutylnaphthalenesulfonate or sodium oleoyl methyl taurate. To prepare wettable powders, the herbicidal active compounds are finely milled by conventional equipment, such as hammer mills, fan mills and air jet mills, and mixed simultaneously or subsequently with the formulation auxiliaries.

[0055] Emulsifiable concentrates are prepared by dissolving the active compounds in an organic solvent (e.g. butanol, cyclohexanone, dimethylformamide, xylene or aromatic compounds or hydrocarbons with relatively high boiling points, or mixtures of solvents) with the addition of one or more surfactants (emulsifiers) of ionic and / or non-ionic type. Examples of emulsifiers that can be used are calcium alkylarylsulfonates (e.g. Ca dodecylbenzenesulfonate) or non-ionic emulsifiers (e.g. fatty acid polyglycol esters, alkylaryl polyglycol ethers, fatty alcohol polyglycol ethers, propylene oxide-ethylene oxide condensates, alkyl polyethers, sorbitan esters (e.g. sorbitan fatty acid esters) or polyoxyethylene sorbitan esters (e.g. polyoxyethylene sorbitan fatty acid esters)).

[0056] Powders are obtained by grinding the active compounds with finely divided solid substances, such as talc, natural clays (e.g. kaolin, bentonite and pyrophyllite) or diatomaceous earth. Suspensions may be aqueous or oily. They can be prepared, for example, by wet milling using conventional commercially available bead mills, with or without the addition of surfactants, as in the case of other formulation types, for example as already mentioned above.

[0057] Emulsions, e.g. oil-in-water emulsions (EW), can be prepared, for example, by means of stirrers, colloid mills and / or static mixers using, for example, aqueous organic solvents and, if desired, surfactants as already mentioned above in the case of other formulation types.

[0058] Granules can be prepared by spraying the active compound onto an absorbent granulated inert material, or by applying the active compound onto the surface of a carrier, such as sand, kaolinite, or a granulated inert material, with a sticky binder, such as polyvinyl alcohol, sodium polyacrylate, or mineral oil.Similarly, suitable active compounds can be mixed with fertilizers as needed and granulated by conventional methods for preparing fertilizer granules.Generally, water-dispersible granules are prepared by conventional methods, such as spray drying, fluidized bed granulation, disk granulation, mixing using a high-speed mixer, and extrusion without solid inert materials.

[0059] For the preparation of granules by disk, fluid bed, extrusion and spraying, see, for example, the methods described in "Spray-Drying Handbook" 3rd ed. 1979, G. Goodwin Ltd., London; JE Browning, "Agglomeration", Chemical and Engineering 1967, pages 147 ff.; "Perry's Chemical Engineer's Handbook", 5th Ed., McGraw-Hill, New York 1973, pp. 8-57. For further details on the formulation of crop protection products, see, for example, GC Klingman, "Weed Control as a Science", John Wiley and Sons Inc., New York, 1961, pages 81-96 and JD Freyer, SA Evans, "Weed Control Handbook", 5th Ed., Blackwell Scientific Publications, Oxford, 1968, pages 101-103.

[0060] Typically, agrochemical formulations contain 0.1-99% by weight, in particular 0.1-95% by weight, of the active compound of formula I. In wettable powders, the concentration of the active compound is, for example, about 10-99% by weight, the remainder consisting of customary formulation constituents being up to 100% by weight. In emulsifiable concentrates, the concentration of the active compound may be, for example, about 1-90% by weight, preferably 5-80% by weight. Formulations in powder form contain 1-30% by weight, preferably most commonly 5-20% by weight, of the active compound, while sprayable solutions contain about 0.05-80% by weight, preferably 2-50% by weight, of the active compound. In the case of water-dispersible granules, the content of the active compound depends in part on whether the active compound is in liquid or solid form and on the granulation aids, fillers used. In water-dispersible granules, the content of the active compound is, for example, 1-95% by weight, preferably 10-80% by weight.

[0061] Additionally, the formulation of the active compound may contain tackifiers, wetting agents, dispersants, emulsifiers, penetrants, preservatives, antifreeze agents, solvents, fillers, carriers, colorants, antifoaming agents, evaporation retardants, pH adjusters and viscosity adjusters, each of which is conventional.

[0062] On the basis of these formulations, it is also possible to produce combinations with other pesticidal active ingredients, e.g. insecticides, acaricides, herbicides and fungicides, as well as combinations with safeners, fertilizers and / or growth regulators, for example in ready-mix or tank-mix form.

[0063] Suitable active compounds that can be combined with the active compounds according to the invention in mixed formulations or tank mixes are known active compounds, for example, as described in World Herbicide New Product Technology Handbook, China Agricultural Science and Farming Techniques Press, September 2010 and the documents cited therein.For example, as herbicides that can be combined with the compounds of formula I, the following active compounds can be mentioned (Note: the compounds are named by their "common name" according to the International Organization for Standardization (ISO) or by their chemical name together with their customary code number, where appropriate): acetochlor, butachlor, alachlor, propisochlor, metolachlor, s-metolachlor, pretilachlor, propachlor, ethachlor, napropamide and R-left handed napropamide (R-left handed napropamide). naproxamide), propanil, mefenacet, diphenamide, diflufenican, ethaprochlor, beflubutamide, bromobutide, dimethenamid, dimethenamid-P, etobenzanide, flufenacet, thenylchlor, metazachlor, isoxaben, flamprop-M-methyl, flamprop-M-propyl, alidochlor, petoxamide, chloranocryl, cyprazine, mefluidide, monalid, delaclor, prinachlor, terbuchlor, xylachlor, dimethachlor, cisanilide, trimexachlor, clo Meprop, propyzamide, pentanochlor, carbetamide, benzoylpropethyl, cyprazole, butenachlor, tebutam, benzipram, mogrton, dichlofluanid, naproanilide, diethatylethyl, naptalam, flufenacet, EL-177, benzadox, chlorthiamide, chlorophthalimide, isocarbamide, picolinafen, atrazine, simazine, prometryn, cyanathrine, simetryn, ametryn, propazine, dipropetryn, SSH-108, terbutryn, terbuthylazine, triaziflam, cyprazine, proglinadine, trietazine, prometon, simeton,Aziprothrin, desmetryn, dimethamethryn, procyazine, mesoprazine, sebutylazine, secbumeton, terbumeton, metoprothrin, cyanatryn, ipazine, chlorazine, atraton, pendimethalin, eglinadine, cyanuric acid, indaziflam, chlorsulfuron, metsulfuron-methyl, bensulfuron-methyl, chlorimuron-ethyl, tribenuron-methyl, thifensulfuron-methyl, pyrazosulfuron-ethyl, mesosulfuron, sodium iodosulfuron methyl, foramsulfuron, cinosulfuron, tria Sulfuron, sulfometuron methyl, nicosulfuron, ethametsulfuron methyl, amidosulfuron, ethoxysulfuron, cyclosulfamuron, rimsulfuron, azimsulfuron, flazasulfuron, monosulfuron, monosulfuron ester, flucarbazone sodium, flupyrsulfuron methyl, halosulfuron methyl, oxasulfuron, imazosulfuron, primisulfuron, propoxycarbazone, prosulfuron, sulfosulfuron, trifloxysulfuron, triflusulfuron methyl, tritosulfuron, me Tosulfuron methyl sodium, flucetosulfuron, HNPC-C, orthosulfamuron, propyrisulfuron, metazosulfuron, acifluorfen, fomesafen, lactofen, fluoroglycofen, oxyfluorfen, chlornitrofen, aclonifen, ethoxyfen ethyl, bifenox, nitrofluorfen, clomethoxyfen, fluorodoifen, fluoronitrofen, freeroxifene, nitrofen, TOPE, DMNP, PPG1013, AKH-7088, halosafen, chlor Toluron, isoproturon, linuron, diuron, daimuron, fluometuron, benzthiazuron, methabenzthiazuron, cumyluron, etidimuron, isouron, tebuthiuron, buturon, chlorbromuron, methyldaimuron, fenobenzuron, SK-85, metobromuron, metoxuron, afesin, monuron, siduron, fenuron, fluothiuron, nebulon, chloroxuron, noruron, isonoruron, 3-cyclooctyl-1, thiazafluron, tebuthiuron, difenoxuron, parafluron,Methylamine tribunil, carbutyrate, trimeturon, dimefuron, monisouron, anisuron, methiuron, chloreturon, tetrafluron, phenmedipham, phenmedipham ethyl, desmedipham, asulam, terbucarb, valban, propham, chlorpropham, rowmate, swep, chlorbufam, carboxazole, chlorprocarb, phenashulam, BCPC, CPPC, carbasulam, butyrate, benthiocarb, vernolate , molinate, triallate, dimepiperate, esprocarb, pyributicarb, cycloate, avadex, EPTC, etiolate, orbencarb, pebulate, prosulfocarb, thiocarbazyl, CDEC, dimexano, isopolynate, methiobencarb, 2,4-D butyl ester, MCPA-Na, 2,4-D isooctyl ester, MCPA isooctyl ester, 2,4-D sodium salt, 2,4-D dimethylamine salt, MCPA-thioethyl, MCPA, 2,4-D propionic acid, high 2,4-D pro propionate, 2,4-D butyrate, MCPA propionate, MCPA propionate, MCPA butyrate, 2,4,5-D, 2,4,5-D propionate, 2,4,5-D butyrate, MCPA amine salt, dicamba, elvon, chlorfenac, saison, TBA, chloramben, methoxy-TBA, diclofop-methyl, fluazifop-butyl, fluazifop-p-butyl, haloxyfop-methyl, haloxyfop-P, quizalofop-ethyl, quizalofop-ethyl, fenoxaprop-ethyl, fenoxaprop-p-etyl Chil, propaquizafop, cyhalofop-butyl, metamifop, clodinafop-propargyl, fenthiaprop-ethyl, chloroazifop-propynyl, poppenate-methyl, trifopsim, isoxapyrifop, paraquat, diquat, oryzalin, ethalfluralin, isoproparin, nitralin, profluralin, prodiamine, benfluralin, fluchloralin, dinitramine,Dipropalin, chlornidine, methaproparin, dinoprop, glyphosate, anilofos, glufosinate ammonium, amiprophos methyl, sulphosate, piperophos, bialaphos sodium, bensulide, butamiphos, focarb, 2,4-DEP, H-9201, zytron, imazapyr, imazethapyr, imazaquin, imazamox, imazamox ammonium salt, imazapic, imazamethabenz methyl, fluroxypyr, fluroxypyr isooctyl ester, clopyralid, pi Chloram, triclopyr, dithiopyr, haloxydine, 3,5,6-trichloro-2-pyridinol, thiazopyr, fluridone, aminopyralid, diflufenzopyr, triclopyr-butotyl, cliodinate, sethoxydim, clethodim, cycloxydim, alloxydim, clefoxydim, butroxydim, tralkoxydim, tepraloxydim, butidazole, metribuzin, hexazinone, metamitron, etiodin, ametridione, amivudine, bromoxynil, bromoxynil octanoate, ioxynil octanoate, ioxynil, Dichlobenil, diphenatryl, pyraclonil, chloroxynil, iodobonyl, flumetsulam, florasulam, penoxsulam, metosullam, cloransulam-methyl, diclosulam, piroxsulam, benfuresate, bispyribac-sodium, pyribenzoxim, pyriftalid, pyriminobac-methyl, pyrithiobac-sodium, benzobisilone, mesotrione, sulcotrione, tembotrione, tephryltrione, bicyclopyrone, ketodpiradox, isoxaflutole, clomazone, fenoxasulfo , methiozoline, fluazolate, pyraflufen-ethyl, pyrazolinate, difenzoquat, pyrazoxyfene, benzofenap, nipiraclofen, pyrasulfotole, topramezone, pyroxasulfone, cafenstrole, flupoxam, aminotriazole, amicarbazone, azafenidin, carfentrazone-ethyl, sulfentrazone, bencarbazone, benzfendizone, butafenacil, bromacil, isocyl, lenacil, terbacil, flupropacil, cinidon-ethyl, flumiclorac-pentyl, flumioxazin,Propyzamide, MK-129, flumezin, pentachlorophenol, dinoseb, dinoterb, dinoterb acetate, dinosam, DNOC, chloronitrophene, medinoterb acetate, dinofenate, oxadiargyl, oxadiazone, pentoxazone, flufenacet, fluthiacet-methyl, fentrazamide, flufenpyr-ethyl, pyrazone, brompyrazone, metofluran, kusakira, dimidazon , oxapyrazon, norflurazon, pyridafol, quinclorac, quinmerac, bentazone, pyridate, oxaziclomefone, benazolin, clomazone, cinmethylin, ZJ0702, pyribambenz-propyl, indanofan, sodium chlorate, dalapon, trichloroacetic acid, monochloroacetic acid, hexachloroacetone, flupropanate, cypercort, bromofenoxime, epronaz, methazole, flurtamone, benfuresate, esofumesate, thioclorim, chlorthal , fluorochloridone, tabron, acrolein, bentlanil, tridiphane, chlorfenprop methyl, thidiarizonaimin, phenisopham, busoxinone, methoxyphenone, saflufenacil, clasifos, chloropon, arorac, diethamcort, etonipromide, iprimidam, ipfencarbazone, thiencarbazone methyl, pyrisulfan, chlorflurazole, tripropindan, s Luglicapine, Prosulfarin, Cambendichlor, Aminocyclopyrachlor, Rodethanil, Benoxacor, Fenclorim, Flurazole, Fenchlorazole Ethyl, Cloquintocet Mexyl, Oxabetrinil (, MG / 91, Cyometrinil, DKA-24, Mefenpyr-Diethyl, Freerazole, Fluxofenim, Isoxadifen Ethyl, Dichlormid, Halauxifen Methyl, DOW Florpyrauxifen, 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.

[0064] The formulations used, present in commercial form, are diluted, if appropriate, in the customary manner, for example with water in the case of wettable powders, emulsifiable concentrates, dispersions and water-dispersible granules. Products in the form of dusts, granules for soil application or scattering and sprayable solutions are usually not further diluted with other inert substances prior to use. The application rate of the compound of formula I required varies depending on the external conditions, for example temperature, humidity, the nature of the herbicide used, etc. It may range widely, for example from 0.001 to 1.0 kg / ha or more, preferably from 0.005 to 750 g / ha, in particular from 0.005 to 250 g / ha of reactive substance. EXAMPLES

[0065] Specific Modes for Carrying Out the Invention The following embodiments are used to describe the present invention in detail, and are not intended to limit the present invention in any way. The scope of the present invention is described through the claims.

[0066] From the viewpoint of economy and diversity of compounds, preferably, multiple compounds are synthesized, some of which are shown in Tables 1 and A below. The structures and information of specific compounds are shown in Tables 1 and A. The compounds in Tables 1 and A are described to further illustrate the present invention, but are not limited thereby. The subject matter of the present invention should not be construed by those skilled in the art as being limited to the following compounds.

[0067] [Table 1-1] [Table 1-2] [Table 1-3] [Table 1-4]

Table 1-5

Table 1-6

Table 1-7

Table 1-8

Table 1-9

Table 1-10

Table 1-11

Table 1-12

Table 1-13

Table 1-14

Table 1-15

Table 1-16

Table 1-17

Table 1-18

Table 1-19

Table 1-20

Table 1-21

Table 1-22

Table 1-23

Table 1-24

Table 1-25

Table 1-26

Table 1-27

Table 1-28

Table 1-29

Table 1-30

Table 1-31

Table 1-32

Table 1-33

Table 1-34

Table 1-35

Table 1-36

Table 1-37

Table 1-38

Table 1-39

Table 1-40

Table 1-41

Table 1-42

Table 1-43

Table 1-44

Table 1-45

Table 1-46

Table 1-47

Table 1-48

Table 1-49

Table 1-50

Table 1-51

Table 1-52

Table 1-53

Table 1-54

Table 1-55

Table 1-56

Table 1-57

Table 1-58

Table 1-59

Table 1-60

Table 1-61

Table 1-62

Table 1-63

Table 1-64

Table 1-65

Table 1-66

Table 1-67

Table 1-68

Table 1-69

Table 1-70

Table 1-71

Table 1-72

Table 1-73

Table 1-74

Table 1-75

Table 1-76

Table 1-77

Table 1-78

Table 1-79

Table 1-80

Table 1-81

Table 1-82

Table 1-83

Table 1-84

Table 1-85

Table 1-86

Table 1-87

Table 1-88

Table 1-89

Table 1-90

Table 1-91

Table 1-92

Table 1-93

Table 1-94

Table 1-95

Table 1-96

Table 1-97

Table 1-98

Table 1-99

Table 1-100

Table 1-101

Table 1-102

Table 1-103

Table 1-104

Table 1-105

Table 1-106

[0068] Table A shows racemic compounds ( [ka] [Wherein, X is -C * X1X2-(alkyl) n -or-alkyl-C * X1X2-(alkyl) n -, i.e., X1 and X2 are not the same, * The carbon atom in is the chiral center. That is, compounds 1 to 188, 193 to 432, 438 to 439, 441 to 469, 471 to 478, 481 to 484, 486 to 493, 495 to 545, 547 to 641, 644 to 669, 672, 674 to 681, 683 to 727, 729 to 829, 832 to 857, 860, 862 to 869, 871 to 916, 918 to 1018, 1021 to 1046, 1049, 1051 to 1058 and 1060 to 1069) are replaced with the corresponding compounds of R configuration, and compounds not having a chiral center at the corresponding position are deleted, but are constructed in the same manner as in Table 1 above. In Table A, the "Number" column is as follows: 1(R)-188(R), 193(R)-432(R), 438(R)-439(R), 441(R)-469(R), 471(R)-478(R), 481(R)-484(R), 486(R)-493(R), 495(R)-545(R), 547(R)-641(R), 644(R)-669(R), 672(R), 674(R) The order of the configurations is as follows: ~681(R), 683(R)~727(R), 729(R)~829(R), 832(R)~857(R), 860(R), 862(R)~869(R), 871(R)~916(R), 918(R)~1018(R), 1021(R)~1046(R), 1049(R), 1051(R)~1058(R), and 1060(R)~1069(R). For example, "1(R)" corresponds to the R-configuration of compound "1" in Table 1, and "194(R)" corresponds to the R-configuration of compound "194" in Table 1.

[0069] The method of preparing the compound of the present invention is described in detail in the following program and embodiment. The materials are commercially available or prepared through known methods reported in the literature or are shown in the route. Those skilled in the art should understand that the compound of the present invention can also be synthesized by other synthetic routes. The detailed materials and reaction conditions in the synthetic route are described in the following text, but they can also be easily replaced by other similar materials and conditions. For example, the isomers of the compound prepared by modifying the preparation method of the present invention are also included in the scope of the present invention. In addition, the following preparation methods can be further modified according to the disclosure of the present invention by general chemical methods known to those skilled in the art, for example, by protecting appropriate groups during the reaction process.

[0070] The following application methods can be used to further understand the preparation method of the present invention. The specific materials, classes and conditions are determined to further explain the present invention, and do not limit its reasonable scope. The reagents of the following synthetic compounds shown in the table can be purchased from the market or can be easily prepared by those skilled in the art.

[0071] Representative examples of compounds are as follows, and the synthesis methods of other compounds are similar and will not be described in detail here.

[0072] 1. Synthesis of Compound 1 1) 1-1 (10 g, 49.1 mmol, 1.0 equiv), Fe powder (8.23 g, 147.4 mmol, 3.0 equiv), NH4Cl (5.26 g, 98.3 mmol, 2.0 equiv) and water (50 mL) were added in sequence to 500 mL of EtOH solution. The reaction solution was then reacted at 80° C. for 1 h. LCMS test showed the disappearance of raw materials. After filtration, the solution was concentrated to remove ethanol and then extracted with ethyl acetate. The organic phase was washed with saturated brine (100 mL×1) and then concentrated to give 1-2 (12 g, crude product) (black solid).

[0073] [ka]

[0074] 2) 1-2 (12 g, 69.1 mmol, 1.0 equiv., crude product) was added to 100 mL of toluene solution. Then 1-3 (10.8 g, 69.1 mmol, 1.0 equiv.) was added to the reaction solution at 100° C. After the addition was completed, the reaction solution was reacted at 100° C. for 1 h. LCMS test showed the disappearance of raw materials and the formation of product. The reaction solution was concentrated to remove toluene. The obtained crude product was separated by column chromatography to obtain 1-4 (5 g) (yellow solid).

[0075] [ka]

[0076] 3) 1-5 (3.8 g, 17.0 mmol, 1.0 equiv.) and AcONa (0.7 g, 8.5 mmol, 0.5 equiv.) were added to 50 mL of DMF solution. Then, 1-4 (5 g, 17.0 mmol, 1.0 equiv.) was added to the reaction solution at 60° C. After the addition was completed, the reaction solution was reacted at 60° C. for 1 h. LCMS test showed the disappearance of raw materials and the appearance of a new peak. After adding water (50 mL), the reaction solution was extracted with ethyl acetate. The organic phase was washed with saturated saline (100 mL×1) and then concentrated. The obtained crude product was separated by column chromatography to obtain 1-6 (4.0 g, 71.3% yield) (white solid).

[0077] [ka]

[0078] 4) 1-6 (4 g, 12.1 mmol, 1.0 equiv) was added to 40 mL of EtOH, and NHOHCl (0.93 g, 13.3 mmol, 1.1 equiv) aqueous solution (6 mL) was added dropwise to the reaction solution at 0°C. After the addition was completed, the reaction solution was stirred at 0°C for 2 h. LCMS test showed that the raw material was almost consumed and one new major peak appeared. The reaction solution was concentrated to remove a part of the ethanol, and then poured into 10 mL of water to precipitate a solid. After filtration, the filter cake was washed with water and dried to give 1-7 (7 g, 71.7% yield) (white solid).

[0079] [ka]

[0080] 5) 1-7 (0.2 g, 0.58 mmol, 1.0 equiv), a (0.14 g, 1.1 mmol, 2 equiv) and K2CO3 (0.24 g, 1.74 mmol, 3 equiv) were added sequentially to 5 mL of DMF solution. The reaction solution was then reacted at room temperature for 4 h. LCMS test showed the disappearance of the raw materials and the presence of all product peaks. After adding water (10 mL), the reaction solution was extracted with ethyl acetate. The organic phase was washed with saturated saline (10 mL x 1) and then concentrated. The obtained crude product was separated by column chromatography to give 1 (0.15 g, 60% yield) (white solid). [ka]

[0081] " 2. Synthesis of compound 1 in the (R) configuration 1-7 (0.2 g, 0.58 mmol, 1.0 equiv), b (0.14 g, 1.1 mmol, 2 equiv), and K2CO3 (0.24 g, 1.74 mmol, 3 equiv) were added sequentially to 5 mL of DMF solution. The reaction solution was then reacted at room temperature for 4 h. LCMS test showed the disappearance of raw materials and the presence of all product peaks. After adding water (10 mL), the reaction solution was extracted with ethyl acetate. The organic phase was washed with saturated saline (10 mL × 1) and then concentrated. The obtained crude product was separated by column chromatography to obtain 1(R) (0.15 g, 60% yield, R / S = 98 / 2) (white solid).

[0082] [ka]

[0083] 3. Synthesis of compound 194(R) 1) 1-1 (20 g, 98.3 mmol, 1.0 equiv) was added to 200 mL of EtOH, and NH2OHHCl (7.5 g, 108.1 mmol, 1.1 equiv) aqueous solution (30 mL) was added dropwise to the reaction solution at 0°C. After the addition was completed, the reaction solution was stirred at 0°C for 3 h. LCMS test showed that the raw material was almost consumed and one new major peak appeared. The reaction solution was concentrated to remove a part of the ethanol, and then poured into 100 mL of water to precipitate a solid. After filtration, the filter cake was washed with water and dried to give 194-1 (20 g, 93% yield) (white solid).

[0084] [ka]

[0085] 2) 194-1 (5 g, 22.9 mmol, 1.0 equiv), Fe powder (3.8 g, 68.6 mmol, 3 equiv), NH4Cl (2.5 g, 45.8 mmol, 2 equiv) and water (10 mL) were added sequentially to 50 mL of EtOH. The reaction solution was then reacted at 80° C. for 1 h. LCMS test showed the appearance of a product peak. The reaction solution was filtered through Celite and then concentrated to remove ethanol. After adding water (20 mL), the reaction solution was extracted with ethyl acetate and then concentrated to obtain a black crude product. This crude product was separated and purified by column chromatography to obtain 194-2 (2 g, 46.4% yield) (gray solid).

[0086] [ka]

[0087] 3) 194-2 (1 g, 5.3 mmol, 1.0 equiv.) and c (1.1 g, 5.3 mmol, 1.0 equiv.) were added to 20 mL of acetic acid, and the reaction solution was reacted at 110° C. for 1 h. LCMS test showed that the reaction of the raw materials was essentially complete, with one major product present. The reaction solution was concentrated to remove the solvent. The resulting crude product was separated by column chromatography to give 194-3 (1.5 g, 80.5% yield) (white solid).

[0088] [ka]

[0089] 4) 194-3 (0.4 g, 1.1 mmol, 1.5 equiv), b (0.18 g, 1.5 mmol, 1.3 equiv) and K2CO3 (0.2 g, 1.5 mmol, 1.3 equiv) were added sequentially to 8 mL of DMF. The reaction solution was then reacted at 25° C. for 4 hours. LCMS test showed the formation of the product. After adding water (10 mL), the reaction solution was extracted with ethyl acetate. The organic phase was washed with saturated saline (10 mL×1) and then concentrated. The obtained crude product was separated by column chromatography to obtain 194-4 (0.3 g, 60.2% yield) (white solid).

[0090] [ka]

[0091] 5) 194-4 (0.3 g, 0.69 mmol, 1.0 equiv), MeI (0.13 g, 0.9 mmol, 1.3 equiv) and K2CO3 (0.12 g, 0.9 mmol, 1.3 equiv) were added sequentially to 6 mL of DMF. The reaction solution was then reacted at 25° C. for 2 h. LCMS test showed the formation of the product. After adding water (10 mL), the reaction solution was extracted with ethyl acetate. The organic phase was washed with saturated saline (10 mL×1) and then concentrated. The obtained crude product was separated by column chromatography to obtain 194(R) (0.2 g, 64.6% yield, R / S=99 / 1) (white solid).

[0092] [ka]

[0093] 4. Synthesis of Compound 504 (1) 504-1 (2 g, 1.0 eq.) and Dess-Martin (4.8 g, 2 eq.) were added to 50 mL of DCM solution. The reaction solution was then reacted at room temperature for 2 hours. LCMS test showed the completion of the reaction. After adding aqueous NaHCO3 (100 mL), the reaction solution was extracted with DCM. The organic phase was washed with saturated saline (100 mL x 2) and then concentrated. The obtained crude product was separated by column chromatography to obtain 504-2 (1.6 g, 82% yield) (white solid).

[0094] [ka]

[0095] (2) 504-2 (1.6 g, 1.0 eq.), water (10 mL), and hydroxylamine hydrochloride (0.63 g, 2 eq.) were added to 30 mL of ethanol solution. The reaction solution was then reacted at room temperature for 2 hours. LCMS test showed the completion of the reaction. The reaction solution was concentrated. The obtained crude product was separated by column chromatography to give 504-3 (1.1 g, 69% yield) (white oil).

[0096] [ka]

[0097] (3) 504-3 (0.3 g, 1.0 eq.) and K2CO3 (170 mg, 1.5 eq.) were added to 10 mL of DMF, then a (150 mg, 1.5 eq.) was added to the reaction solution at 25° C., and then reacted at 25° C. for 8 hours. LCMS test showed the formation of the product. After adding water (10 mL), the reaction solution was extracted with ethyl acetate. The organic phase was washed with saturated saline (20 mL×1) and then concentrated. The obtained crude product was separated by column chromatography to obtain 504 (0.2 g, 54% yield) (white solid).

[0098] [ka]

[0099] 5. Synthesis of Compound 919 (1) 919-1 (0.3 g, 1.0 eq.) and NH2NH2H2O (0.5 g, 85% aqueous solution, 10 eq.) were added to 10 mL of THF. The reaction solution was then stirred at 60° C. for 3 h. LCMS test showed the formation of the product. The reaction solution was concentrated. The obtained crude product was separated by column chromatography to give 919-2 (0.15 g, 48% yield) (white solid).

[0100] [ka]

[0101] (2) 919-2 (0.15 g, 1.0 eq.) and K2CO3 (74 mg, 1.3 eq.) were added to 6 mL of DMF, then a (55 mg, 1.1 eq.) was added to the reaction solution at 25° C., and then reacted at 25° C. for 8 hours. LCMS test showed the formation of the product. After adding water (10 mL), the reaction solution was extracted with ethyl acetate. The organic phase was washed with saturated saline (20 mL×1) and then concentrated. The obtained crude product was separated by column chromatography to obtain 919 (50 mg, 27% yield) (white solid).

[0102] [ka]

[0103] Biological activity evaluation The activity level criteria for plant injury (i.e., percent growth inhibition) are as follows: Level 5: Growth inhibition rate is 85% or more Level 4: Growth inhibition rate is 60% or more but less than 85% Level 3: Growth inhibition rate is between 40% and 60% Level 2: Growth inhibition rate is between 20% and 40% Level 1: Growth inhibition rate is between 5% and 20% Level 0: Growth inhibition rate is less than 5%

[0104] The above growth inhibition rates are those of fresh weight.

[0105] Experiments on herbicidal efficacy at the post-emergence stage Monocotyledonous and dicotyledonous weed seeds (Descurainia sophia, Capsella bursa-pastoris, Abutilon theophrasti, Galium aparine, Stellaria media, Lithospermum arvense, Rorippa indica, Alopecurus aequalis, Alopecurus japonicus, Eleusine indica, Beckmannia syzigachne, Sclerochloa dura, Conyza Canadensis, Phleum paniculatum, Veronica didyma Tenore, Bromus japonicus, Aegilops tauschii, Phalaris arundinacea, Amaranthus retroflexus, Chenopodiaceae, Commelina communis, Sonchus arvensis, Convolvulus arvensis, Cirsium setosum, Bidens tripartita L.), nightshade (Solanum nigrum), Chinese hackberry (Acalypha australis), crabgrass (Digitaria sanguinalis), barnyard grass (Echinochloa crusgalli), green foxtail (Setaria viridis), golden foxtail (Setaria glauca), Japanese knotweed (Leptochloa chinensis), Japanese boxwood (Monochoria vaginalis), arrowhead (Sagittaria trifolia), bulrush (Scirpus juncoides), nutsedge (Cyperus rotundus), Japanese yarrow (Cyperus iria), Japanese yarrow (Cyperus difformis), Japanese burdock (Fimbristylis), purslane (Portulaca oleracea), Xanthium Seeds of major crops (wheat, corn, rice, soybean, cotton, rapeseed, millet, sorghum, potato, sesame, castor, etc.) were placed in plastic pots filled with soil, then covered with 0.5-2 cm of soil and grown in a good environment in a greenhouse. Two weeks after sowing, the test plants were treated at the 2-3 leaf stage. The test compounds of the present invention were each dissolved in acetone, then Tween 80 and an emulsifiable concentrate of methyl oleate (1.5 liters / ha) were added as a synergist, and diluted with a certain amount of water to obtain a solution of a certain concentration, which was sprayed on the plants by a sprayer. After application, the plants were cultivated in a greenhouse for 3 weeks, and then the experimental results of weed control were compiled. The doses of compounds used were 500 g / ha, 250 g / ha, 125 g / ha, 60 g / ha, 30 g / ha, 15 g / ha and 7.5 g / ha, with three replicates to obtain the average values. Representative data are shown in Table 2.

[0106] [Table 2-1] [Table 2-2] [Table 2-3] [Table 2-4] [Table 2-5] [Table 2-6] [Table 2-7]

[0107] Notes: N means not tested. Control compound A: [ka] Control compound B: [ka] Control compound C: [ka] Control compound D: [ka] Control compound E: [ka] Control compound F: [ka]

[0108] [Table 3]

[0109] Experiments on herbicidal effects at the pre-emergence stage The seeds of the above monocotyledonous and dicotyledonous weeds and major crops were placed in plastic pots containing soil and covered with 0.5 to 2 cm of soil. The test compound of the present invention was dissolved in acetone, then Tween 80 was added, and the solution was diluted with a certain amount of water to a certain concentration, and sprayed immediately after sowing. After spraying the obtained seeds, they were cultivated in a greenhouse for 4 weeks, and the test results were observed. It was confirmed that most of the herbicides had excellent effects, especially against weeds such as barnyard grass (Echinochloa crusgalli), crabgrass (Digitaria sanguinalis), and velvetleaf (Abutilon theophrasti), at spray rates of 500 g ai / ha, 250 g ai / ha, 125 g ai / ha, 60 g ai / ha, 30 g ai / ha, 15 g ai / ha, and 7.5 g ai / ha. In addition, many of the compounds had good selectivity against corn, cotton, wheat, rice, soybean, peanut, etc. In addition, the weed control effect is evaluated according to the above activity standard level. Many of the compounds showed excellent activity and selectivity, and the results are shown in Table 4.

[0110] [Table 4]

[0111] Tests on major weeds in wheat fields and rice fields have shown that the compounds of the present invention have good weed control effects in general. In particular, it is noteworthy that the compounds of the present invention have extremely high activity against broadleaf weeds and cyperaceae weeds that are resistant to ALS inhibitors, such as Sagittaria trifolia, Scirpus juncoides, Cyperus difformis, Descurainia sophia, Capsella bursa-pastoris, Lithospermum arvense, Galium aparine L., and Cyperus rotundus L., and have excellent commercial value.

[0112] Evaluation of the safety of transplanted rice in paddy fields and evaluation of the effectiveness of weed control Rice field soil was placed in a 1 / 1,000,000ha pot. Seeds of Echinochloa crusgalli, Scirpus juncoides, Bidens tripartita L., Monochoria vaginalis, and Leptochloa chinensis were sown, gently covered with soil, and then placed in a greenhouse with 0.5-1cm of water. The next day or two days later, tubers of Sagittaria trifolia were planted. Thereafter, the pots were kept with 3-4cm of water. When barnyard grass (Echinochloa crusgalli), bulrush (Scirpus juncoides), Bidens tripartita L., Monochoria vaginalis and Leptochloa chinensis reached the 0.5-leaf stage, and arrowhead (Sagittaria trifolia) reached the primary leaf stage, a WP or SC water dilution prepared according to the general preparation method of the compound of the present invention was uniformly dropped with a pipette to a predetermined effective amount to treat the weeds.

[0113] Furthermore, the soil of the rice field placed in the 1 / 1,000,000ha pot was leveled and the water was retained at a depth of 3 to 4 cm. The next day, rice (Japonica rice) at the 85-leaf stage was transplanted at a transplanting depth of 3 cm. Five days after transplanting, the compound of the present invention was similarly applied.

[0114] The fertility conditions of Echinochloa crusgalli, Scirpus juncoides, Bidens tripartita L., Monochoria vaginalis, Leptochloa chinensis and Sagittaria trifolia were visually confirmed 14 days after application of the compound of the present invention, and the fertility conditions of rice plants 21 days after application of the compound of the present invention. The weed control effect is evaluated according to the above activity standard level. Many compounds show excellent activity and selectivity.

[0115] [Table 5]

[0116] Note: Seeds of Echinochloa crusgalli, Scirpus juncoides, Monochoria vaginalis, Bidens tripartita L., and Leptochloa chinensis were collected from Heilongjiang Province, China. Tests showed that these weeds are resistant to pyrazosulfuron-ethyl at common doses.

[0117] Activity Testing of Compositions The active ingredients B bipyrazone, ciprolafluone, fenpyrazone and tripyrasulfone are manufactured by our company. [ka] The preparation method of was as follows, and the others were purchased from a reagent company. All technical materials were dissolved in acetone and diluted with an aqueous solution containing the emulsifier Tween-80 at 0.1%. Dilution was performed as necessary.

[0118] (1) Compound: [ka] Synthesis of (1.1) Compound 1 (cpd1) (3 g, 16 mmol, 1.0 eq.), NaOH (0.72 g, 18 mmol, 1.1 eq.) were added successively to 30 mL of DMF, and then compound 2 (cpd2) (1.28 g, 16.8 mmol, 1.05 eq.) was added dropwise at 0 °C, and the reaction solution was stirred at 0 °C for 1 h. LCMS test showed that the reaction of the raw material was essentially complete, and one new major peak was present. The reaction solution was poured into 30 mL of water, the mixture was separated, the aqueous phase was extracted once with 50 mL of ethyl acetate, and the resulting organic phase was washed three times with saturated brine (50 mL), dried, evaporated to dryness under reduced pressure, and separated by column chromatography to obtain compound 3 (cpd3) (3.6 g, 91% yield) (colorless oil).

[0119] [ka]

[0120] (1.2) Compound 3 (cpd3) (3.1 g, 13 mmol, 1.0 equiv.) was added to 30 mL of THF, and then n-BuLi (6.42 mL, 2.5 M, 16 mmol, 1.2 equiv.) was slowly added at -78 ° C., and then the reaction solution was stirred at -78 ° C. for 0.5 h, CO2 was slowly supplied for 10 min, and then the reaction solution was slowly warmed to room temperature. The product was detected by LCMS. 20 mL of water was poured into the reaction solution, the mixture was separated, and the aqueous phase was extracted once with 30 mL of ethyl acetate, and the obtained aqueous phase was gradually adjusted to pH = 4-5 with concentrated hydrochloric acid, filtered, and dried to obtain compound 4 (cpd4) (3.2 g, 87% yield) (white solid).

[0121] [ka]

[0122] (1.3) Compound 4 (cpd4) (3.1 g, 11 mmol, 1.0 equivalent), compound 5 (Cpd5) (1.66 g, 16.8 mmol, 1.5 equivalent), and DMAP (0.13 g, 1.1 mmol, 0.1 equivalent) were added sequentially to 30 mL of pyridine. Then, SOCl2 (2.0 g, 16.8 mmol, 1.5 equivalent) was slowly added at 0 °C, and the reaction solution was stirred at room temperature for 3 hours. The product was detected by LCMS. Pyridine was concentrated and removed, and then 30 mL of water was poured into the reaction solution and the mixture was separated. The aqueous phase was extracted three times with 30 mL of ethyl acetate, and the obtained organic phase was washed three times with saturated saline (50 mL), dried, evaporated to dryness under reduced pressure, and separated by column chromatography to obtain compound 6 (cpd6) (2.5 g, 63% yield) (white solid).

[0123] [ka]

[0124] (1.4) Compound 6 (cpd6) (1 g, 2.8 mmol, 1.0 eq.) and m-CPBA (0.54 g, 3.1 mmol, 1.1 eq.) were added sequentially to 10 mL of dichloromethane. The reaction solution was then stirred at room temperature for 1 h. The product was detected by LCMS, and the reaction of the raw material was essentially complete. The reaction solution was poured into 10 mL of water, the reaction was quenched with sodium hydrogen sulfite, and the mixture was separated. The aqueous phase was extracted three times with 30 mL of dichloromethane, and the resulting organic phase was washed once with saturated saline (30 mL), dried, evaporated to dryness under reduced pressure, and separated by column chromatography to obtain compound 7 (cpd7) (0.85 g, 82% yield) (off-white solid). 1 H NMR (500 MHz, DMSO-d6) 12.57 (s, 1H), 8.07 (dd, J = 8.0, 7.0 Hz, 1H), 7.82 (d, J = 8.0 Hz, 1H), 3.57-3.47 (m, 2H), 2.48 (s, 3H), 1.70-1.52 (m, 2H), 1.08-0.93 (m, 3H).

[0125] [ka]

[0126] (1.5) Compound 7 (cpd7) (0.5 g, purity 98%) was separated by chiral HPLC (column: CHIRALPAK IG; column size: 3 cm × 25 cm, 5 μm; injection volume: 3.0 mL; mobile phase: Hex (0.2% FA): IPA = 50:50; flow rate: 28 mL / min; wavelength: UV254 nm; temperature: 25 °C; sample solution: 70 mg / mL in EtOH / DCM; run time = 60 min) and then concentrated to give compound B1 (R-configuration) (0.16 g, Rt = 10.51 min, 100% ee, purity 98%) as a white solid, which was confirmed by single crystal diffraction.

[0127] [ka]

[0128] (2) Compound: [ka] Synthesis of (2.1) Compound a (0.5 g, 2.13 mmol), compound b (313 mg, 2.55 mmol), a catalytic amount of TBAB (10 mg), and DMF (10 mL) were charged into a round-bottom flask and stirred at room temperature (15° C.) for 24 hours. If a small amount of raw material remained as detected by LC-MS, further treatment was carried out. The reaction solution was poured into 50 mL of water and extracted twice with methyl tert-butyl ether (50 mL×2). The organic phase was dried, concentrated, and separated by column chromatography to obtain compound c (300 mg, 50% yield) as a white solid.

[0129] [ka]

[0130] (2.2) Compound c (0.3 g, 1.06 mmol) and methanol (20 mL) were charged into a 100 mL one-neck flask. Lithium hydroxide (44.5 mg, 1.06 mmol) was dissolved in 2 mL of water and slowly added dropwise to the one-neck flask at room temperature, then stirred at room temperature for 12 hours. After the reaction of the raw materials was completed by LC-MS detection, the reaction solution was adjusted to pH=5-6 with 0.5 M dilute hydrochloric acid, concentrated, and then extracted with water and ethyl acetate. The organic phase was dried and concentrated to obtain compound d (200 mg, 70% yield) as a white solid.

[0131] [ka]

[0132] (2.3) Compound d (200 mg, 0.74 mmol), compound e (75 mg, 0.74 mmol), DCC (152 mg, 0.74 mmol) and anhydrous DCM (20 mL) were charged into a 100 mL round-bottom flask and reacted at room temperature for 12 hours. After the reaction of the raw materials was completed by LC-MS detection, the reaction solution was concentrated and separated by column chromatography to obtain compound B2 (200 mg, 77% yield) as a white solid.

[0133] [ka] 1 H NMR (500 MHz, Chloroform-d) δ 5.28 (q, J = 7.0 Hz, 1H), 5.15 (s, 2H), 4.27 - 4.07 (m, 3H), 3.91 - 3.73 (m, 2H), 2.04 - 1.82 (m, 3H), 1.66 (d, J = 7.0 Hz, 3H), 1.59-1.54 (m, 1H).

[0134] (A) Post-emergence treatment by foliar spraying Weeds were grown using the pot culture method. Plastic nutritional bowls measuring 180 × 140 mm were filled 4 / 5 with field topsoil and placed in enamel pans, where the soil had been air-dried and sieved and had an initial moisture content of 20%. Whole and uniform weed seeds were selected, soaked in hot water at 25 °C for 6 h, and germinated in a biochemical incubator (dark room) at 28 °C. Freshly germinated weed seeds were placed evenly on the soil surface and covered with 0.5-1 cm of soil depending on the size of the seeds.

[0135] Cultivation was carried out in a controlled sunlight greenhouse at 20–30°C, natural light, and 57–72% relative humidity. The soil was loam with an organic matter content of 1.63%, a pH value of 7.1, alkaline hydrolyzable nitrogen of 84.3 mg / kg, fast-acting phosphorus of 38.5 mg / kg, and fast-acting potassium of 82.1 mg / kg.

[0136] Each pot contained 20 weed seeds, 3 pots per treatment, and 4 replicates per treatment.

[0137] Chemicals were used only once during the experiment. When the weeds reached the 1.5-2 leaf stage, they were thinned out to maintain 10 weeds per pot, with 30 weeds per treatment. Conyza canadensis was then grown until it reached a height of 10 cm, and the other weeds until they reached the 3-4 leaf stage, at which point they were treated.

[0138] Fully cultivated weeds in an area of ​​0.5 m 2 The weeds were evenly placed on a platform, and the herbicide solution was sprayed onto the foliage at a dose of 450 kg / ha and a spray pressure of 0.3 MPa using a 3WP-2000-type walking spray tower. After all the solution was sprayed, the valve was closed. After 30 seconds, the door of the spray tower was opened and the vegetative pots were removed. The valve was then opened and 50 mL of water was sprayed to clean the spray tube. After treatment, the weeds were routinely cultivated in a greenhouse.

[0139] (B) Soil containment treatment Weeds were grown in a controllable sunlight greenhouse at 20-30°C, natural light, and 57-72% relative humidity. The soil was loam with an organic matter content of 1.63%, a pH value of 7.1, alkaline hydrolyzable nitrogen of 84.3 mg / kg, fast-acting phosphorus of 38.5 mg / kg, and fast-acting potassium of 82.1 mg / kg. The test soil was quantitatively filled to 3 / 4 of the pot, and then water was poured in from the bottom of the pot to moisten the soil to full saturation. Test weed seeds were germinated, sown uniformly and quantitatively on the surface, covered with soil 0.5-2 cm deep depending on the size of the seeds, and ready for use 72 hours after sowing.

[0140] Thirty weed seeds were planted per pot, with three pots as one treatment, and four replicates per treatment.

[0141] Thoroughly sown weeds in an area of ​​0.5 m 2 The soil was evenly placed on a platform, and the chemical solution was sprayed onto the soil at a dose of 450 kg / ha with a spray pressure of 0.3 MPa using a 3WP-2000 walking spray tower. After all the solution was sprayed, the valve was closed. After 30 seconds, the door of the spray tower was opened and the nutrient pots were removed. The valve was then opened and 50 mL of water was sprayed to clean the spray tube.

[0142] (C) Data research and statistical analysis An absolute count method was used, in which all live weeds were cut along the soil surface with a blade and the fresh weight of the weeds was weighed on an analytical balance. The fresh weight of dead weeds was set to zero.

[0143] The examination was carried out once only, 21 days after treatment.

[0144] The theoretical fresh weight inhibition rate of the combination of two active ingredients in each group was calculated by the Gowing method (E0=X+YX×Y / 100), and then compared with the actually measured inhibition rate (E) to evaluate the effect of the combination on weeds (hereinafter referred to as composite effect). An E-E0 value of more than 10% corresponds to a synergistic effect, an E-E0 value of less than -10% corresponds to an antagonistic effect, and an E-E0 value of -10% to 10% corresponds to an additive effect. The optimal ratio of the two active ingredients was determined according to the balance of the actual control effect, the properties of the herbicides, and the corresponding calculation formula. In the calculation formula, X represents the fresh weight inhibition rate of active ingredient A at dosage P, and Y represents the fresh weight inhibition rate of active ingredient B at dosage Q. The statistical results are shown in Table 6.

[0145] [Table 6-1] [Table 6-2] [Table 6-3]

[0146] Furthermore, the present invention also provides other specific combinations of component A and component B, and more specifically describes the components of the present invention. In Table 1, the compounds in the column "Component A (Compound Number)" are identified. The second column of Table B1 lists specific compounds of component B (e.g., "Topramezone" in the first row). The remaining rows of Table B1 are similarly structured.

[0147] [Table 7-1] [Table 7-2]

[0148] Table B2 is structured similarly to Table B1 above, except that the entries in the column "Component A (Compound Number)" are replaced with the corresponding entries in the column "Component A (Compound Number)" shown below. Thus, for example, in Table B2, the entries in the column "Component A (Compound Number)" are all represented by "2" (i.e., Compound 2 identified in Table 1), and a mixture of Compound 2 and "Topramezone" is specifically described in the first line under the heading of Table B2. Tables B3 to B547 are also structured similarly.

[0149] [Table 8-1] [Table 8-2] [Table 8-3]

[0150] Table C1 is structured similarly to the above Table B1, except that the entries in the "Component A (Compound Number)" column are replaced with the corresponding entries in the "Component A (Compound Number)" column shown below. Thus, for example, in Table C1, the entries in the "Component A (Compound Number)" column are all represented as "1(R)" (i.e., the R configuration of Compound 1 identified in Table A), and a mixture of Compound 1(R) and "Top La Maison" is specifically described in the first line under the heading of Table C1. Tables C2 to C532 are also structured similarly.

[0151] [Table 9-1] [Table 9-2] [Table 9-3]

[0152] At the same time, through some tests, it has been found that the compounds and compositions of the present invention have good selectivity against many grasses, such as zoysia japonica, bermuda grass, tall fescue, bluegrass, ryegrass, seashore paspalum, etc., and can control many important grasses and broadleaf weeds. The compounds also show excellent selectivity and commercial value in tests on sugarcane, soybean, cotton, oil sunflower, potato, fruit trees and vegetables in different herbicide application methods.

Claims

1. General formula I: 【Chemistry 1】 [In the formula, Q has the following formula: 【Chemistry 2】 represents a group represented by Y represents halogen, haloalkyl or cyano; Z represents a halogen; M represents CH or N; X is -CX １ X ２ - (alkyl) ｎ -, -alkyl-CX １ X ２ - (alkyl) ｎ - or - (CH ２ ) ｒ - represents X １ , X ２ are each independently H, halogen, cyano, amino, nitro, formyl, cyanoalkyl, hydroxyalkyl, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, alkoxy, alkylthio, alkylamino, haloalkoxy, haloalkylthio, alkylcarbonyl, alkoxycarbonyl, alkoxyalkyl, haloalkoxyalkyl, alkylaminoalkyl, aryl, heterocyclyl, arylalkyl, or heterocyclylalkyl; and X １ , X ２ is not simultaneously hydrogen, wherein "alkyl", "alkenyl" and "alkynyl" are each independently unsubstituted or substituted with halogen, and "cycloalkyl", "cycloalkylalkyl", "aryl", "heterocyclyl", "arylalkyl" and "heterocyclylalkyl" are each independently unsubstituted or substituted with oxo, halogen, cyano, nitro, alkyl, alkenyl, alkynyl, cycloalkyl, haloalkyl, haloalkenyl, haloalkynyl, halocycloalkyl, cycloalkyl substituted with alkyl, -OR １３ , -SR １３ , -(CO)OR １３ , -(SO ２ ) R １３ , -N(R １３ ) ２ and -O-alkyl-(CO)OR １３ or two adjacent carbon atoms on the ring are substituted with at least one group selected from the group consisting of —OCH ２ CH ２ -or-OCH ２ O- together form a condensed ring, Q １ , Q ２ , Q ３ , Q ４ , Q ５ each independently represents O or S; R １ , R ２ are each independently H, cyano, alkyl, alkenyl, alkynyl, formylalkyl, cyanoalkyl, amino, aminoalkyl, aminocarbonyl, aminocarbonylalkyl, aminosulfonyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl, cycloalkenylalkyl, heterocyclyl, heterocyclylalkyl, aryl, arylalkyl, R ４ R ５ N-(CO)-NR ３ - , the following formula: 【Chemistry 3】 A group represented by R ３ -S (O) ｍ - (alkyl) ｎ -, R ３ -O-(alkyl) ｎ -, R ３ -(CO)-(alkyl) ｎ -, R ３ -O-(alkyl) ｎ -(CO)-, R ３ -(CO)-O-(alkyl) ｎ -, R ３ -S-(CO)-(alkyl) ｎ -, R ３ -O-(CO)-alkyl- or R ３ -O-(CO)-O-alkyl-, where "alkyl", "alkenyl", and "alkynyl" are each independently unsubstituted or substituted with halogen, and "amino", "aminoalkyl", "aminocarbonyl", "aminocarbonylalkyl", and "aminosulfonyl" are each independently unsubstituted or substituted with -R １１ , -OR １１ , -(CO)R １１ , -(CO)OR １１ , -alkyl-(CO)OR １１ , -(SO ２ ) R １１ , -(SO ２ ) OR １１ , -alkyl-(SO ２ ) R １１ , -(CO)N(R １２ ) ２ and -(SO ２ ) N (R １２ ) ２ and each of "cycloalkyl", "cycloalkylalkyl", "cycloalkenyl", "cycloalkenylalkyl", "heterocyclyl", "heterocyclylalkyl", "aryl" and "arylalkyl" is independently unsubstituted or substituted with oxo, halogen, cyano, nitro, alkyl, alkenyl, alkynyl, cycloalkyl, haloalkyl, haloalkenyl, haloalkynyl, halocycloalkyl, cycloalkyl substituted with alkyl, -OR １３ , -SR １３ , -(CO)OR １３ , -(SO ２ ) R １３ , -N(R １３ ) ２ and -O-alkyl-(CO)OR １３ or two adjacent carbon atoms on the ring are substituted with at least one group selected from the group consisting of —OCH ２ CH ２ -or-OCH ２ O- together form a condensed ring, R ６ represents alkyl, alkenyl, alkynyl, or cyano, where each of "alkyl", "alkenyl", and "alkynyl" is independently unsubstituted or substituted with at least one group selected from halogen, alkoxy, and alkoxycarbonyl; R ７ , R ７ ', R ８ , R ８ each ' independently represents H, alkyl, halogen, haloalkyl, amino, hydroxyalkyl, or alkoxy; R ３ , R ４ , R ５ each independently represent H, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl, cycloalkenylalkyl, heterocyclyl, heterocyclylalkyl, aryl, or arylalkyl, where "alkyl", "alkenyl", and "alkynyl" are each independently unsubstituted or substituted with halogen, and "cycloalkyl", "cycloalkylalkyl", "cycloalkenyl", "cycloalkenylalkyl", "heterocyclyl", "heterocyclylalkyl", "aryl" and "arylalkyl" are each independently unsubstituted or substituted with oxo, halogen, cyano, nitro, alkyl, alkenyl, alkynyl, cycloalkyl, haloalkyl, haloalkenyl, haloalkynyl, halocycloalkyl, cycloalkyl substituted with alkyl, -OR １３ , -SR １３ , -(CO)OR １３ , -(SO ２ ) R １３ , -N(R １３ ) ２ and -O-alkyl-(CO)OR １３ or two adjacent carbon atoms on the ring are substituted with at least one group selected from the group consisting of —OCH ２ CH ２ -or-OCH ２ O- together form a condensed ring, R １１ independently represent alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl, cycloalkenylalkyl, phenyl, benzyl, where "alkyl", "alkenyl" and "alkynyl" are each independently unsubstituted or substituted with halogen, and "phenyl" and "benzyl" are each independently unsubstituted or substituted with at least one group selected from halogen, cyano, nitro, alkyl, haloalkyl, alkoxycarbonyl, alkylthio, alkylsulfonyl, alkoxy, and haloalkoxy; R １２ independently represent H, alkyl, alkenyl, alkynyl, alkoxy, alkylsulfonyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl, or cycloalkenylalkyl, or -(CO)N(R １２ ) ２ Or - (SO ２ ) N (R １２ ) ２ N in (R １２ ) ２ each independently represents an unsubstituted or substituted heterocyclyl having a nitrogen atom at position 1, R １３ represents independently H; alkyl; haloalkyl; phenyl; or phenyl substituted with at least one group selected from halogen, cyano, nitro, alkyl, haloalkyl, alkoxycarbonyl, alkylthio, alkylsulfonyl, alkoxy, and haloalkoxy; r represents 2, 3, 4, 5 or 6; m represents 0, 1 or 2; n independently represents 0 or 1; W is for OX ５ , S.X. ５ Or N(X ５ ) ２ represents X ３ , X ４ each independently represents O, S, NH or N-alkyl; When W represents OX 5 or SX 5 , X ５ is H, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, heterocyclyl, aryl, or a group of the formula: 【Chemistry 4】 When W represents N(X 5 ) 2 , X 5 represents H, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, heterocyclyl, aryl, or a group represented by the following formula: 【Chemistry 5】 wherein "alkyl", "alkenyl" and "alkynyl" are each independently unsubstituted or selected from halogen, cyano, nitro, cycloalkyl, cycloalkenyl, heterocyclyl, aryl, and the following formula: 【Chemistry 6】 and each of "cycloalkyl", "cycloalkenyl", "heterocyclyl" and "aryl" is independently unsubstituted or substituted with at least one group selected from the group represented by oxo, halogen, cyano, nitro, alkyl, alkenyl, alkynyl, cycloalkyl, haloalkyl, haloalkenyl, haloalkynyl, halocycloalkyl, cycloalkyl substituted with alkyl, -OR １３ , -SR １３ , -(CO)OR １３ , -(SO ２ ) R １３ , -N(R １３ ) ２ and -O-alkyl-(CO)OR １３ or two adjacent carbon atoms on the ring are substituted with at least one group selected from the group consisting of —OCH ２ CH ２ -or-OCH ２ O- together to form a condensed ring, or N(X ５ ) ２ is the following formula: 【Chemistry 7】 or an unsubstituted or substituted heterocyclyl having a nitrogen atom at position 1, X １１ is independently H, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl, cycloalkenylalkyl, heterocyclyl, heterocyclylalkyl, aryl, arylalkyl, or a group of the formula: 【Chemistry 8】 wherein "cycloalkyl", "cycloalkylalkyl", "cycloalkenyl", "cycloalkenylalkyl", "heterocyclyl", "heterocyclylalkyl", "aryl" and "arylalkyl" are each independently unsubstituted or substituted with oxo, halogen, cyano, nitro, alkyl, alkenyl, alkynyl, cycloalkyl, haloalkyl, haloalkenyl, haloalkynyl, halocycloalkyl, cycloalkyl substituted with alkyl, -OR １３ , -SR １３ , -(CO)OR １３ , -(SO ２ ) R １３ , -N(R １３ ) ２ and -O-alkyl-(CO)OR １３ or two adjacent carbon atoms on the ring are substituted with at least one group selected from the group consisting of —OCH ２ CH ２ -or-OCH ２ O- together form a condensed ring, X １２ independently represent alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl, cycloalkenylalkyl, heterocyclyl, heterocyclylalkyl, aryl, or arylalkyl, where "cycloalkyl", "cycloalkylalkyl", "cycloalkenyl", "cycloalkenylalkyl", "heterocyclyl", "heterocyclylalkyl", "aryl" and "arylalkyl" are each independently unsubstituted or substituted with oxo, halogen, cyano, nitro, alkyl, alkenyl, alkynyl, cycloalkyl, haloalkyl, haloalkenyl, haloalkynyl, halocycloalkyl, cycloalkyl substituted with alkyl, -OR １３ , -SR １３ , -(CO)OR １３ , -(SO ２ ) R １３ , -N(R １３ ) ２ and -O-alkyl-(CO)OR １３ or two adjacent carbon atoms on the ring are substituted with at least one group selected from the group consisting of —OCH ２ CH ２ -or-OCH ２ O- together form a condensed ring, X １３ , X １４ each independently represents H, halogen, cyano, alkoxy, alkoxyalkyl, alkylcarbonyl, alkoxycarbonyl, alkylsulfonyl, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl, cycloalkenylalkyl, aryl, arylalkyl, heterocyclyl, or heterocyclylalkyl; or X １３ and X １４ together with the carbon atom to which they are attached form an unsubstituted or substituted cyclic structure, or X １３ and X １４ together with the nitrogen atom to which they are attached form an unsubstituted or substituted heterocyclyl having a nitrogen atom at position 1, where "alkyl", "alkenyl", and "alkynyl" are each independently unsubstituted or substituted with halogen, and "cycloalkyl", "cycloalkylalkyl", "cycloalkenyl", "cycloalkenylalkyl", "aryl", "arylalkyl", "heterocyclyl", and "heterocyclylalkyl" are each independently unsubstituted or substituted with oxo, halogen, cyano, nitro, alkyl, alkenyl, alkynyl, cycloalkyl, haloalkyl, haloalkenyl, haloalkynyl, halocycloalkyl, cycloalkyl substituted with alkyl, -OR １３ , -SR １３ , -(CO)OR １３ , -(SO ２ ) R １３ , -N(R １３ ) ２ and -O-alkyl-(CO)OR １３ or two adjacent carbon atoms on the ring are substituted with at least one group selected from the group consisting of —OCH ２ CH ２ -or-OCH ２ Together with O-, they form a condensed ring. The iminoaryl compound substituted with a carboxylic acid derivative is represented by the following formula:

2. Y represents halogen, haloC1-C8 alkyl or cyano; X is -CX １ X ２ -(C1-C8 alkyl) ｎ -, -(C1-C8 alkyl)-CX １ X ２ -(C1-C8 alkyl) ｎ - or - (CH ２ ) ｒ - represents X １ , X ２ are each independently H, halogen, cyano, amino, nitro, formyl, cyanoC1-C8 alkyl, hydroxyC1-C8 alkyl, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkylC1-C8 alkyl, C1-C8 alkoxy, C1-C8 alkylthio, C1-C8 alkylamino, haloC1-C8 alkoxy, haloC1-C8 alkylthio, C1-C8 alkylcarbonyl, C1-C8 alkoxycarbonyl, C1-C8 alkoxyC1-C8 alkyl, haloC1-C8 alkoxyC1-C8 alkyl, C1-C8 alkylaminoC1-C8 alkyl, aryl, heterocyclyl, arylC1-C8 alkyl or heterocyclylC1-C8 alkyl; and X １ , X ２ but are not simultaneously hydrogen, wherein "C1-C8 alkyl", "C2-C8 alkenyl" and "C2-C8 alkynyl" are each independently unsubstituted or substituted with halogen, and "C3-C8 cycloalkyl", "C3-C8 cycloalkylC1-C8 alkyl", "aryl", "heterocyclyl", "arylC1-C8 alkyl" and "heterocyclylC1-C8 alkyl" are each independently unsubstituted or substituted with oxo, halogen, cyano, nitro, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, haloC1-C8 alkyl, haloC2-C8 alkenyl, haloC2-C8 alkynyl, haloC3-C8 cycloalkyl, C3-C8 cycloalkyl substituted with C1-C8 alkyl, -OR １３ , -SR １３ , -(CO)OR １３ , -(SO ２ ) R １３ , -N(R １３ ) ２ and -O-(C1-C8 alkyl)-(CO)OR １３ or two adjacent carbon atoms on the ring are substituted with at least one group selected from the group consisting of —OCH ２ CH ２ -or-OCH ２ O- together form a condensed ring, R １ , R ２ are each independently H, cyano, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, formylC1-C8 alkyl, cyanoC1-C8 alkyl, amino, aminoC1-C8 alkyl, aminocarbonyl, aminocarbonylC1-C8 alkyl, aminosulfonyl, C3-C8 cycloalkyl, C3-C8 cycloalkylC1-C8 alkyl, C3-C8 cycloalkenyl, C3-C8 cycloalkenylC1-C8 alkyl, heterocyclyl, heterocyclylC1-C8 alkyl, aryl, arylC1-C8 alkyl, R ４ R ５ N-(CO)-NR ３ - , the following formula: 【Chemistry 9】 A group represented by R ３ -S (O) ｍ -(C1-C8 alkyl) ｎ -, R ３ -O-(C1-C8 alkyl) ｎ -, R ３ -(CO)-(C1-C8 alkyl) ｎ -, R ３ -O-(C1-C8 alkyl) ｎ -(CO)-, R ３ -(CO)-O-(C1-C8 alkyl) ｎ -, R ３ -S-(CO)-(C1-C8 alkyl) ｎ -, R ３ -O-(CO)-(C1-C8 alkyl)- or R ３ represents —O—(CO)—O—(C1-C8 alkyl)-, in which “C1-C8 alkyl”, “C2-C8 alkenyl”, and “C2-C8 alkynyl” are each independently unsubstituted or substituted with halogen, and “amino”, “amino C1-C8 alkyl”, “aminocarbonyl”, “aminocarbonyl C1-C8 alkyl”, and “aminosulfonyl” are each independently unsubstituted or substituted with —R １１ , -OR １１ , -(CO)R １１ , -(CO)OR １１ , -(C1-C8 alkyl)-(CO)OR １１ , -(SO ２ ) R １１ , -(SO ２ ) OR １１ , -(C1-C8 alkyl)-(SO ２ ) R １１ , -(CO)N(R １２ ) ２ and -(SO ２ ) N (R １２ ) ２ and "C3-C8 cycloalkyl", "C3-C8 cycloalkyl C1-C8 alkyl", "C3-C8 cycloalkenyl", "C3-C8 cycloalkenyl C1-C8 alkyl", "heterocyclyl", "heterocyclyl C1-C8 alkyl", "aryl" and "aryl C1-C8 alkyl" are each independently unsubstituted or substituted with 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 with C1-C8 alkyl, -OR １３ , -SR １３ , -(CO)OR １３ , -(SO ２ ) R １３ , -N(R １３ ) ２ and -O-(C1-C8 alkyl)-(CO)OR １３ or two adjacent carbon atoms on the ring are substituted with at least one group selected from the group consisting of —OCH ２ CH ２ -or-OCH ２ O- together form a condensed ring, R ６ represents C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, or cyano, where "C1-C8 alkyl", "C2-C8 alkenyl", and "C2-C8 alkynyl" are each independently unsubstituted or substituted with at least one group selected from halogen, C1-C8 alkoxy, and C1-C8 alkoxycarbonyl; R ７ , R ７ ', R ８ , R ８ each ' independently represents H, C1-C8 alkyl, halogen, haloC1-C8 alkyl, amino, hydroxyC1-C8 alkyl, or C1-C8 alkoxy; R ３ , R ４ , R ５ each independently represent H, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkylC1-C8 alkyl, C3-C8 cycloalkenyl, C3-C8 cycloalkenylC1-C8 alkyl, heterocyclyl, heterocyclylC1-C8 alkyl, aryl, or arylC1-C8 alkyl, where "C1-C8 alkyl", "C2-C8 alkenyl", and "C2-C8 alkynyl" are each independently unsubstituted or substituted with halogen, and "C3-C8 cycloalkyl", "C3-C8 cycloalkylC1-C8 alkyl" and "C3-C8 cycloalkylC1-C8 alkyl" are each independently unsubstituted or substituted with halogen, "1-C8 alkyl", "C3-C8 cycloalkenyl", "C3-C8 cycloalkenyl C1-C8 alkyl", "heterocyclyl", "heterocyclyl C1-C8 alkyl", "aryl" and "aryl C1-C8 alkyl" are each independently unsubstituted or substituted with 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 with C1-C8 alkyl, -OR １３ , -SR １３ , -(CO)OR １３ , -(SO ２ ) R １３ , -N(R １３ ) ２ and -O-(C1-C8 alkyl)-(CO)OR １３ or two adjacent carbon atoms on the ring are substituted with at least one group selected from the group consisting of —OCH ２ CH ２ -or-OCH ２ O- together form a condensed ring, R １１ independently represent C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkylC1-C8 alkyl, C3-C8 cycloalkenyl, C3-C8 cycloalkenylC1-C8 alkyl, phenyl, benzyl, wherein "C1-C8 alkyl", "C2-C8 alkenyl", and "C2-C8 alkynyl" are each independently unsubstituted or substituted with halogen, and "phenyl" and "benzyl" are each independently unsubstituted or substituted with at least one group selected from halogen, cyano, nitro, C1-C8 alkyl, haloC1-C8 alkyl, C1-C8 alkoxycarbonyl, C1-C8 alkylthio, C1-C8 alkylsulfonyl, C1-C8 alkoxy, and haloC1-C8 alkoxy; R １２ independently represent H, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C1-C8 alkoxy, C1-C8 alkylsulfonyl, C3-C8 cycloalkyl, C3-C8 cycloalkylC1-C8 alkyl, C3-C8 cycloalkenyl or C3-C8 cycloalkenylC1-C8 alkyl, or -(CO)N(R １２ ) ２ Or - (SO ２ ) N (R １２ ) ２ N in (R １２ ) ２ is independently selected from the following formula: 【Chemistry 10】 represents a heterocyclyl represented by the formula: R １３ represent independently H; C1-C8 alkyl; halo C1-C8 alkyl; phenyl; or phenyl substituted with 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, and halo C1-C8 alkoxy; X ３ , X ４ each independently represents O, S, NH, or N-(C1-C8)alkyl; When W represents OX 5 or SX 5 , X ５ is H, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkenyl, heterocyclyl, aryl, or the following formula: 【Chemistry 11】 When W represents N(X 5 ) 2 , X 5 represents H, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkenyl, heterocyclyl, aryl, or a group represented by the following formula: 【Chemistry 12】 wherein "C1-C8 alkyl", "C2-C8 alkenyl" and "C2-C8 alkynyl" are each independently unsubstituted or selected from halogen, cyano, nitro, C3-C8 cycloalkyl, C3-C8 cycloalkenyl, heterocyclyl, aryl, and the following formula: 【Chemistry 13】 and each of "C3-C8 cycloalkyl", "C3-C8 cycloalkenyl", "heterocyclyl" and "aryl" is independently unsubstituted or substituted with 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 with C1-C8 alkyl, -OR １３ , -SR １３ , -(CO)OR １３ , -(SO ２ ) R １３ , -N(R １３ ) ２ and -O-(C1-C8 alkyl)-(CO)OR １３ or two adjacent carbon atoms on the ring are substituted with at least one group selected from the group consisting of —OCH ２ CH ２ -or-OCH ２ O- together to form a condensed ring, or N(X ５ ) ２ is expressed by the following formula: 【Chemistry 14】 or a group represented by the following formula, which is unsubstituted or substituted with at least one group selected from oxo and C1-C8 alkyl, having a nitrogen atom at position 1: 【Chemistry 15】 represents a heterocyclyl represented by the formula: X １１ are independently H, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, halo C1-C8 alkyl, halo C2-C8 alkenyl, halo C2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkyl C1-C8 alkyl, C3-C8 cycloalkenyl, C3-C8 cycloalkenyl C1-C8 alkyl, heterocyclyl, heterocyclyl C1-C8 alkyl, aryl, aryl C1-C8 alkyl, or the formula: 【Chemistry 16】 wherein "C3-C8 cycloalkyl", "C3-C8 cycloalkyl C1-C8 alkyl", "C3-C8 cycloalkenyl", "C3-C8 cycloalkenyl C1-C8 alkyl", "heterocyclyl", "heterocyclyl C1-C8 alkyl", "aryl" and "aryl C1-C8 alkyl" are each independently unsubstituted or substituted with 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 with C1-C8 alkyl, -OR １３ , -SR １３ , -(CO)OR １３ , -(SO ２ ) R １３ , -N(R １３ ) ２ and -O-(C1-C8 alkyl)-(CO)OR １３ or two adjacent carbon atoms on the ring are substituted with at least one group selected from the group consisting of —OCH ２ CH ２ -or-OCH ２ O- together form a condensed ring, X １２ independently represent C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, halo C1-C8 alkyl, halo C2-C8 alkenyl, halo C2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkylC1-C8 alkyl, C3-C8 cycloalkenyl, C3-C8 cycloalkenylC1-C8 alkyl, heterocyclyl, heterocyclylC1-C8 alkyl, aryl, or arylC1-C8 alkyl, wherein "C3-C8 cycloalkyl", "C3-C8 cycloalkylC1-C8 alkyl", "C3-C8 cycloalkenylC1-C8 alkyl" and "C3-C8 cycloalkenylC1-C8 alkyl" are "Alkenyl", "C3-C8 cycloalkenyl C1-C8 alkyl", "heterocyclyl", "heterocyclyl C1-C8 alkyl", "aryl" and "aryl C1-C8 alkyl" are each independently unsubstituted or substituted with 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 with C1-C8 alkyl, -OR １３ , -SR １３ , -(CO)OR １３ , -(SO ２ ) R １３ , -N(R １３ ) ２ and -O-(C1-C8 alkyl)-(CO)OR １３ or two adjacent carbon atoms on the ring are substituted with at least one group selected from the group consisting of —OCH ２ CH ２ -or-OCH ２ O- together form a condensed ring, X １３ , X １４ each independently represents H, halogen, cyano, C1-C8 alkoxy, C1-C8 alkoxyC1-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 cycloalkylalkyl, C3-C8 cycloalkenyl, C3-C8 cycloalkenylC1-C8 alkyl, aryl, arylC1-C8 alkyl, heterocyclyl or heterocyclylC1-C8 alkyl; or X １３ and X １４ together with the carbon atom to which they are attached form a 5- to 8-membered carbocyclyl or oxygen-, sulfur- or nitrogen-containing heterocyclyl, or X １３ and X １４ are taken together with the nitrogen atom to which they are attached to form a heterocyclyl having a nitrogen atom at position 1, in which "C1-C8 alkyl", "C2-C8 alkenyl" and "C2-C8 alkynyl" are each independently unsubstituted or substituted with a halogen, and are also included in the following: "C3-C8 cycloalkyl", "C3-C8 cycloalkylC1-C8 alkyl", "C3-C8 cycloalkenyl", "C3-C8 cycloalkenylC1-C8 alkyl", "aryl", "Aryl C1-C8 alkyl", "heterocyclyl" and "heterocyclyl C1-C8 alkyl" are each independently unsubstituted or selected from the group consisting of 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 with C1-C8 alkyl, -OR １３ , -SR １３ , -(CO)OR １３ , -(SO ２ ) R １３ , -N(R １３ ) ２ and -O-(C1-C8 alkyl)-(CO)OR １３ or two adjacent carbon atoms on the ring are substituted with at least one group selected from the group consisting of —OCH ２ CH ２ -or-OCH ２ and O- together to form a fused ring, and the "5-8 membered carbocyclyl or oxygen-, sulfur- or nitrogen-containing heterocyclyl" is unsubstituted or substituted with 1 to 4 groups selected from C1-C8 alkyl, C1-C8 alkoxycarbonyl and benzyl, or together with an aryl or heterocyclyl to form a fused ring, and the "heterocyclyl having a nitrogen atom at position 1" is unsubstituted or substituted with at least one group selected from oxo and C1-C8 alkyl. The iminoaryl compound substituted with a carboxylic acid derivative according to claim 1 .

3. Y represents halogen, haloC1-C6 alkyl or cyano; X is -CX １ X ２ -(C1-C6 alkyl) ｎ -, -(C1-C6 alkyl)-CX １ X ２ -(C1-C6 alkyl) ｎ - or - (CH ２ ) ｒ - represents X １ , X ２ are each independently H, halogen, cyano, amino, nitro, formyl, cyano C1-C6 alkyl, hydroxy C1-C6 alkyl, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C6 alkyl, C1-C6 alkoxy, C1-C6 alkylthio, C1-C6 alkylamino, halo C1-C6 alkoxy, halo C1-C6 alkylthio, C1-C6 alkylcarbonyl, C1-C6 alkoxycarbonyl, C1-C6 alkoxy C1-C6 alkyl, halo C1-C6 alkoxy C1-C6 alkyl, C1-C6 alkylamino C1-C6 alkyl, aryl, heterocyclyl, aryl C1-C6 alkyl, or heterocyclyl C1-C6 alkyl; and X １ , X ２ but are not simultaneously hydrogen, wherein "C1-C6 alkyl", "C2-C6 alkenyl" and "C2-C6 alkynyl" are each independently unsubstituted or substituted with halogen, and "C3-C6 cycloalkyl", "C3-C6 cycloalkylC1-C6 alkyl", "aryl", "heterocyclyl", "arylC1-C6 alkyl" and "heterocyclylC1-C6 alkyl" are each independently unsubstituted or substituted with oxo, halogen, cyano, nitro, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, haloC1-C6 alkyl, haloC2-C6 alkenyl, haloC2-C6 alkynyl, haloC3-C6 cycloalkyl, C3-C6 cycloalkyl substituted with C1-C6 alkyl, -OR １３ , -SR １３ , -(CO)OR １３ , -(SO ２ ) R １３ , -N(R １３ ) ２ and -O-(C1-C6 alkyl)-(CO)OR １３ or two adjacent carbon atoms on the ring are substituted with —OCH ２ CH ２ -or-OCH ２ O- together form a condensed ring, R １ , R ２ are each independently H, cyano, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, formyl C1-C6 alkyl, cyano C1-C6 alkyl, amino, amino C1-C6 alkyl, aminocarbonyl, aminocarbonyl C1-C6 alkyl, aminosulfonyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C6 alkyl, C3-C6 cycloalkenyl, C3-C6 cycloalkenyl C1-C6 alkyl, heterocyclyl, heterocyclyl C1-C6 alkyl, aryl, aryl C1-C6 alkyl, R ４ R ５ N-(CO)-NR ３ - , the following formula: 【Chemistry 17】 A group represented by R ３ -S (O) ｍ -(C1-C6 alkyl) ｎ -, R ３ -O-(C1-C6 alkyl) ｎ -, R ３ -(CO)-(C1-C6 alkyl) ｎ -, R ３ -O-(C1-C6 alkyl) ｎ -(CO)-, R ３ -(CO)-O-(C1-C6 alkyl) ｎ -, R ３ -S-(CO)-(C1-C6 alkyl) ｎ -, R ３ -O-(CO)-(C1-C6 alkyl)- or R ３ represents —O—(CO)—O—(C1-C6 alkyl)-, where “C1-C6 alkyl”, “C2-C6 alkenyl”, and “C2-C6 alkynyl” are each independently unsubstituted or substituted with halogen, and “amino”, “amino C1-C6 alkyl”, “aminocarbonyl”, “aminocarbonyl C1-C6 alkyl”, and “aminosulfonyl” are each independently unsubstituted or substituted with —R １１ , -OR １１ , -(CO)R １１ , -(CO)OR １１ , -(C1-C6 alkyl)-(CO)OR １１ , -(SO ２ ) R １１ , -(SO ２ ) OR １１ , -(C1-C6 alkyl)-(SO ２ ) R １１ , -(CO)N(R １２ ) ２ and -(SO ２ ) N (R １２ ) ２ and "C3-C6 cycloalkyl", "C3-C6 cycloalkyl C1-C6 alkyl", "C3-C6 cycloalkenyl", "C3-C6 cycloalkenyl C1-C6 alkyl", "heterocyclyl", "heterocyclyl C1-C6 alkyl", "aryl" and "aryl C1-C6 alkyl" are each independently unsubstituted or 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 with C1-C6 alkyl, -OR １３ , -SR １３ , -(CO)OR １３ , -(SO ２ ) R １３ , -N(R １３ ) ２ and -O-(C1-C6 alkyl)-(CO)OR １３ or two adjacent carbon atoms on the ring are substituted with —OCH ２ CH ２ -or-OCH ２ O- together form a condensed ring, R ６ represents C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl or cyano, where "C1-C6 alkyl", "C2-C6 alkenyl" and "C2-C6 alkynyl" are each independently unsubstituted or substituted with 1, 2 or 3 groups selected from halogen, C1-C6 alkoxy and C1-C6 alkoxycarbonyl; R ７ , R ７ ', R ８ , R ８ ' each independently represent H, C1-C6 alkyl, halogen, haloC1-C6 alkyl, amino, hydroxyC1-C6 alkyl, or C1-C6 alkoxy; R ３ , R ４ , R ５ each independently represents H, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkylC1-C6 alkyl, C3-C6 cycloalkenyl, C3-C6 cycloalkenylC1-C6 alkyl, heterocyclyl, heterocyclylC1-C6 alkyl, aryl, or arylC1-C6 alkyl, wherein "C1-C6 alkyl", "C2-C6 alkenyl", and "C2-C6 alkynyl" are each independently unsubstituted or substituted with halogen, and "C3-C6 cycloalkyl", "C3-C6 cycloalkylC1-C6 alkyl" and "C3-C6 cycloalkylC1-C6 alkyl" are each independently unsubstituted or substituted with halogen, "1-C6 alkyl", "C3-C6 cycloalkenyl", "C3-C6 cycloalkenyl C1-C6 alkyl", "heterocyclyl", "heterocyclyl C1-C6 alkyl", "aryl" and "aryl C1-C6 alkyl" are each independently unsubstituted or substituted with 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 with C1-C6 alkyl, -OR １３ , -SR １３ , -(CO)OR １３ , -(SO ２ ) R １３ , -N(R １３ ) ２ and -O-(C1-C6 alkyl)-(CO)OR １３ or two adjacent carbon atoms on the ring are substituted with —OCH ２ CH ２ -or-OCH ２ O- together form a condensed ring, R １１ independently represent C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkylC1-C6 alkyl, C3-C6 cycloalkenyl, C3-C6 cycloalkenylC1-C6 alkyl, phenyl, benzyl, wherein "C1-C6 alkyl", "C2-C6 alkenyl" and "C2-C6 alkynyl" are each independently unsubstituted or substituted with halogen, and "phenyl" and "benzyl" are each independently unsubstituted or substituted with 1, 2 or 3 groups selected from halogen, cyano, nitro, C1-C6 alkyl, haloC1-C6 alkyl, C1-C6 alkoxycarbonyl, C1-C6 alkylthio, C1-C6 alkylsulfonyl, C1-C6 alkoxy and haloC1-C6 alkoxy; R １２ independently represent H, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 alkoxy, C1-C6 alkylsulfonyl, C3-C6 cycloalkyl, C3-C6 cycloalkylC1-C6 alkyl, C3-C6 cycloalkenyl or C3-C6 cycloalkenylC1-C6 alkyl, or -(CO)N(R １２ ) ２ Or - (SO ２ ) N (R １２ ) ２ N in (R １２ ) ２ is independently a nitrogen atom at position 1, unsubstituted or substituted with 1, 2 or 3 groups selected from oxo and C1-C6 alkyl, of the following formula: 【Chemistry 18】 represents a heterocyclyl represented by the formula: R １３ represents independently H; C1-C6 alkyl; halo C1-C6 alkyl; phenyl; or phenyl substituted by one, two or three 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 and halo C1-C6 alkoxy; X ３ , X ４ each independently represents O, S, NH, or N-(C1-C6)alkyl; When W represents OX 5 or SX 5 , X ５ is H, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkenyl, heterocyclyl, aryl, or the following formula: 【Chemistry 19】 When W represents N(X 5 ) 2 , X 5 represents H, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkenyl, heterocyclyl, aryl, or a group represented by the following formula: 【Chemistry 20】 wherein "C1-C6 alkyl", "C2-C6 alkenyl" and "C2-C6 alkynyl" are each independently unsubstituted or selected from halogen, cyano, nitro, C3-C6 cycloalkyl, C3-C6 cycloalkenyl, heterocyclyl, aryl, and the following formula: 【Chemistry 21】 and each of "C3-C6 cycloalkyl", "C3-C6 cycloalkenyl", "heterocyclyl" and "aryl" is independently unsubstituted or 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 with C1-C6 alkyl, -OR １３ , -SR １３ , -(CO)OR １３ , -(SO ２ ) R １３ , -N(R １３ ) ２ and -O-(C1-C6 alkyl)-(CO)OR １３ or two adjacent carbon atoms on the ring are substituted with —OCH ２ CH ２ -or-OCH ２ O- together to form a condensed ring, or N(X ５ ) ２ is expressed by the following formula: 【Chemical 22】 or a group represented by the following formula, which is unsubstituted or substituted with 1, 2 or 3 groups selected from oxo and C1-C6 alkyl, having a nitrogen atom at position 1: 【Chemistry 23】 represents a heterocyclyl represented by the formula: X １１ are independently H, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, halo C1-C6 alkyl, halo C2-C6 alkenyl, halo C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C6 alkyl, C3-C6 cycloalkenyl, C3-C6 cycloalkenyl C1-C6 alkyl, heterocyclyl, heterocyclyl C1-C6 alkyl, aryl, aryl C1-C6 alkyl, or the formula: 【Chemistry 24】 wherein "C3-C6 cycloalkyl", "C3-C6 cycloalkyl C1-C6 alkyl", "C3-C6 cycloalkenyl", "C3-C6 cycloalkenyl C1-C6 alkyl", "heterocyclyl", "heterocyclyl C1-C6 alkyl", "aryl" and "aryl C1-C6 alkyl" are each independently unsubstituted or substituted with 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 with C1-C6 alkyl, -OR １３ , -SR １３ , -(CO)OR １３ , -(SO ２ ) R １３ , -N(R １３ ) ２ and -O-(C1-C6 alkyl)-(CO)OR １３ or two adjacent carbon atoms on the ring are substituted with —OCH ２ CH ２ -or-OCH ２ O- together form a condensed ring, X １２ independently represent C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, halo C1-C6 alkyl, halo C2-C6 alkenyl, halo C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C6 alkyl, C3-C6 cycloalkenyl, C3-C6 cycloalkenyl C1-C6 alkyl, heterocyclyl, heterocyclyl C1-C6 alkyl, aryl or aryl C1-C6 alkyl, wherein "C3-C6 cycloalkyl", "C3-C6 cycloalkyl C1-C6 alkyl", "C3-C6 cycloa "Alkenyl", "C3-C6 cycloalkenyl C1-C6 alkyl", "heterocyclyl", "heterocyclyl C1-C6 alkyl", "aryl" and "aryl C1-C6 alkyl" are each independently unsubstituted or substituted with 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 with C1-C6 alkyl, -OR １３ , -SR １３ , -(CO)OR １３ , -(SO ２ ) R １３ , -N(R １３ ) ２ and -O-(C1-C6 alkyl)-(CO)OR １３ or two adjacent carbon atoms on the ring are substituted with —OCH ２ CH ２ -or-OCH ２ O- together form a condensed ring, X １３ , X １４ each independently represents H, halogen, cyano, C1-C6 alkoxy, C1-C6 alkoxyC1-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 cycloalkylalkyl, C3-C6 cycloalkenyl, C3-C6 cycloalkenylC1-C6 alkyl, aryl, arylC1-C6 alkyl, heterocyclyl or heterocyclylC1-C6 alkyl, or X １３ and X １４ together with the carbon atom to which they are attached form a 5- to 8-membered carbocyclyl or oxygen-, sulfur- or nitrogen-containing heterocyclyl, or X １３ and X １４ which, together with the nitrogen atom to which they are attached, form the following formula having a nitrogen atom at the 1-position: 【Chemistry 25】 wherein "C1-C6 alkyl", "C2-C6 alkenyl", and "C2-C6 alkynyl" are each independently unsubstituted or substituted with halogen, and "C3-C6 cycloalkyl", "C3-C6 cycloalkyl C1-C6 alkyl", "C3-C6 cycloalkenyl", "C3-C6 cycloalkenyl C1-C6 alkyl", "aryl", "aryl C1-C6 alkyl", "heterocyclyl", and "heterocyclyl C1-C6 alkyl" are each independently unsubstituted or substituted with 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 with C1-C6 alkyl, -OR １３ , -SR １３ , -(CO)OR １３ , -(SO ２ ) R １３ , -N(R １３ ) ２ and -O-(C1-C6 alkyl)-(CO)OR １３ or two adjacent carbon atoms on the ring are substituted with —OCH ２ CH ２ -or-OCH ２ and O- together to form a fused ring, and the "5-8 membered carbocyclyl or oxygen-, sulfur- or nitrogen-containing heterocyclyl" is unsubstituted or substituted with 1, 2 or 3 groups selected from C1-C6 alkyl, C1-C6 alkoxycarbonyl and benzyl, or forms a fused ring together with an aryl or heterocyclyl, and "has the following formula: 【Chemistry 26】 "Heterocyclyl represented by the formula (I)" is unsubstituted or substituted with 1, 2 or 3 groups selected from oxo and C1-C6 alkyl; The iminoaryl compound substituted with a carboxylic acid derivative according to claim 1 .

4. X is -CX １ X ２ -(C1-C3 alkyl) ｎ -, -(C1-C3 alkyl)-CX １ X ２ -(C1-C3 alkyl) ｎ - or - (CH ２ ) ｒ - represents X １ , X ２ are each independently H, halogen, cyano, amino, nitro, formyl, cyano C1-C3 alkyl, hydroxy C1-C3 alkyl, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C3 alkyl, C1-C6 alkoxy, C1-C6 alkylthio, C1-C6 alkylamino, halo C1-C6 alkoxy, halo C1-C6 alkylthio, C1-C6 alkylcarbonyl, C1-C6 alkoxycarbonyl, C1-C6 alkoxy C1-C3 alkyl, halo C1-C6 alkoxy C1-C3 alkyl, C1-C6 alkylamino C1-C3 alkyl, aryl, heterocyclyl, aryl C1-C3 alkyl, or heterocyclyl C1-C3 alkyl; and X １ , X ２ but are not simultaneously hydrogen, wherein "C1-C6 alkyl", "C2-C6 alkenyl" and "C2-C6 alkynyl" are each independently unsubstituted or substituted with halogen, and "C3-C6 cycloalkyl", "C3-C6 cycloalkyl C1-C3 alkyl", "aryl", "heterocyclyl", "aryl C1-C3 alkyl" and "heterocyclyl C1-C3 alkyl" are each independently unsubstituted or substituted with 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 with C1-C6 alkyl, -OR １３ , -SR １３ , -(CO)OR １３ , -(SO ２ ) R １３ , -N(R １３ ) ２ and -O-(C1-C3 alkyl)-(CO)OR １３ or two adjacent carbon atoms on the ring are substituted with —OCH ２ CH ２ -or-OCH ２ O- together form a condensed ring, When W represents OX 5 or SX 5 , X ５ is H, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkenyl, heterocyclyl, aryl, or the following formula: 【Chemical 27】 When W represents N(X 5 ) 2 , X 5 represents H, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkenyl, heterocyclyl, aryl, or a group represented by the following formula: 【Chemistry 28】 wherein "C1-C6 alkyl", "C2-C6 alkenyl" and "C2-C6 alkynyl" are each independently unsubstituted or selected from halogen, cyano, nitro, C3-C6 cycloalkyl, C3-C6 cycloalkenyl, heterocyclyl, aryl, and the following formula: 【Chemical formula 29】 and "C3-C6 cycloalkyl", "C3-C6 cycloalkenyl", "heterocyclyl" and "aryl" are each independently unsubstituted or 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 with C1-C6 alkyl, -OR １３ , -SR １３ , -(CO)OR １３ , -(SO ２ ) R １３ , -N(R １３ ) ２ and -O-(C1-C3 alkyl)-(CO)OR １３ or two adjacent carbon atoms on the ring are substituted with —OCH ２ CH ２ -or-OCH ２ O- together to form a condensed ring, or N(X ５ ) ２ is expressed by the following formula: 【Chemistry 30】 or a group represented by the following formula, which is unsubstituted or substituted with 1, 2 or 3 groups selected from oxo and C1-C6 alkyl, having a nitrogen atom at position 1: 【Chemistry 31】 represents a heterocyclyl represented by the formula: X １１ are independently H, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, halo C1-C6 alkyl, halo C2-C6 alkenyl, halo C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C3 alkyl, C3-C6 cycloalkenyl, C3-C6 cycloalkenyl C1-C3 alkyl, heterocyclyl, heterocyclyl C1-C3 alkyl, aryl, aryl C1-C3 alkyl, or the formula: 【Chemistry 32】 wherein "C3-C6 cycloalkyl", "C3-C6 cycloalkyl C1-C3 alkyl", "C3-C6 cycloalkenyl", "C3-C6 cycloalkenyl C1-C3 alkyl", "heterocyclyl", "heterocyclyl C1-C3 alkyl", "aryl" and "aryl C1-C3 alkyl" are each independently unsubstituted or substituted with 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 with C1-C6 alkyl, -OR １３ , -SR １３ , -(CO)OR １３ , -(SO ２ ) R １３ , -N(R １３ ) ２ and -O-(C1-C3 alkyl)-(CO)OR １３ or two adjacent carbon atoms on the ring are substituted with —OCH ２ CH ２ -or-OCH ２ O- together form a condensed ring, X １２ independently represent C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, halo C1-C6 alkyl, halo C2-C6 alkenyl, halo C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C3 alkyl, C3-C6 cycloalkenyl, C3-C6 cycloalkenyl C1-C3 alkyl, heterocyclyl, heterocyclyl C1-C3 alkyl, aryl, or aryl C1-C3 alkyl, wherein "C3-C6 cycloalkyl", "C3-C6 cycloalkyl C1-C3 alkyl", "C3-C6 cycloa "Alkenyl", "C3-C6 cycloalkenyl C1-C3 alkyl", "heterocyclyl", "heterocyclyl C1-C3 alkyl", "aryl" and "aryl C1-C3 alkyl" are each independently unsubstituted or substituted with 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 with C1-C6 alkyl, -OR １３ , -SR １３ , -(CO)OR １３ , -(SO ２ ) R １３ , -N(R １３ ) ２ and -O-(C1-C3 alkyl)-(CO)OR １３ or two adjacent carbon atoms on the ring are substituted with —OCH ２ CH ２ -or-OCH ２ O- together form a condensed ring, X １３ , X １４ each independently represents H, halogen, cyano, C1-C6 alkoxy, C1-C6 alkoxyC1-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 cycloalkylalkyl, C3-C6 cycloalkenyl, C3-C6 cycloalkenylC1-C3 alkyl, aryl, arylC1-C3 alkyl, heterocyclyl or heterocyclylC1-C3 alkyl, or X １３ and X １４ together with the carbon atom to which they are attached form a 5-8 membered saturated carbocyclyl or a group of the formula: 【Chemical 33】 or X １３ and X １４ which, together with the nitrogen atom to which they are attached, form the following formula having a nitrogen atom at the 1-position: 【Chemical 34】 wherein "C1-C6 alkyl", "C2-C6 alkenyl", and "C2-C6 alkynyl" are each independently unsubstituted or substituted with halogen, and "C3-C6 cycloalkyl", "C3-C6 cycloalkyl C1-C3 alkyl", "C3-C6 cycloalkenyl", "C3-C6 cycloalkenyl C1-C3 alkyl", "aryl", "aryl C1-C3 alkyl", "heterocyclyl", and "heterocyclyl C1-C3 alkyl" are each independently unsubstituted or substituted with 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 with C1-C6 alkyl, -OR １３ , -SR １３ , -(CO)OR １３ , -(SO ２ ) R １３ , -N(R １３ ) ２ and -O-(C1-C3 alkyl)-(CO)OR １３ or two adjacent carbon atoms on the ring are substituted with —OCH ２ CH ２ -or-OCH ２ and O- together form a fused ring, and are "5- to 8-membered saturated carbocyclyl, or 【Chemistry 35】 is unsubstituted or substituted with one, two or three groups selected from C1-C6 alkyl, C1-C6 alkoxycarbonyl and benzyl, or forms a condensed ring together with phenyl or thienyl, and is represented by the following formula: 【Chemical 36】 Heterocyclyl represented by the formula: is unsubstituted or substituted with 1, 2 or 3 groups selected from oxo and C1-C6 alkyl. The iminoaryl compound substituted with a carboxylic acid derivative according to claim 1 .

5. Q is of the formula: 【Chemical 37】 The iminoaryl compound substituted with a carboxylic acid derivative according to claim 1, characterized in that it represents a group represented by:

6. In the general formula, X １ and X ２ The iminoaryl compound substituted with a carboxylic acid derivative according to claim 1, characterized in that, if the carbon atom connected to is a chiral center, it is of R configuration and has a stereochemical purity of 60 to 100% (R) based on the content of stereoisomers having R and S configurations at this position.

7. The following compounds 1 to 1069: 【Chemical Formula 38】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 and compounds having the R configuration of compounds 1 to 188, 193 to 432, 438 to 439, 441 to 469, 471 to 478, 481 to 484, 486 to 493, 495 to 545, 547 to 641, 644 to 669, 672, 674 to 681, 683 to 727, 729 to 829, 832 to 857, 860, 862 to 869, 871 to 916, 918 to 1018, 1021 to 1046, 1049, 1051 to 1058, and 1060 to 1069, １ and X ２ A compound having a chiral center at a carbon atom connected to The iminoaryl compound substituted with a carboxylic acid derivative according to any one of claims 1 to 6, which is any one selected from the following:

8. A method for preparing an iminoaryl compound substituted with a carboxylic acid derivative according to any one of claims 1 to 7, comprising the steps of: The compound represented by the general formula II and the compound represented by the general formula III are subjected to an elimination reaction, and the reaction is carried out according to the following chemical reaction formula: 【Chemical 39】 obtaining a compound of general formula I by Including, Here, Hal represents a halogen, and the other substituents Q, M, W, Y, Z, X, and X ３ and X ４ is as defined in any one of claims 1 to 7.

9. 9. The method of claim 8, wherein the reaction is carried out in the presence of a base and a solvent, the base being at least one selected from an inorganic base and an organic base, and the solvent being at least one selected from DMF, methanol, ethanol, acetonitrile, dichloroethane, DMSO, dioxane, dichloromethane and ethyl acetate.

10. A herbicidal composition comprising (i) a herbicidally effective amount of at least one iminoaryl compound substituted with a carboxylic acid derivative according to any one of claims 1 to 7, and (ii) a herbicidally effective amount of one or more other herbicides and / or safeners, The other herbicide is the following compound: (1) Topramezone, isoxaflutole, tembotrione, teflurtrione, bipyrazone, ciprolafluone, tripyrasulfone, fenpyrazone, and compounds of the following formula: 【Chemistry 40】 an HPPD inhibitor selected from the compounds represented by (2) a PDS inhibitor selected from flurtamone, diflufenican, and picolinafen; (3) a DOXP inhibitor selected from clomazone and bixlozone; (4) ALS inhibitors selected from tribenuron methyl, thifensulfuron methyl, pyrazosulfuron ethyl, thiencarbazone methyl, halosulfuron methyl, rimsulfuron, nicosulfuron and imazamox; (5) An ACCase inhibitor selected from clethodim, sethoxydim, and quizalofop-P-methyl; (6) PPO inhibitors selected from oxyfluorfen, oxadiazon, oxadiargyl, sulfentrazone, pyraclonil, flumioxazin, saflufenacil, carfentrazone-ethyl, and trifludimoxazine; (7) PSII inhibitors selected from metribuzin, terbuthylazine, amicarbazone, chlortoluron, isoproturon, bromacil, propanil, desmedipham, phenmedipham, bentazone and bromoxynil; (8) a microtubule polymerization inhibitor selected from butruarin and pendimethalin; (9) VLCFA inhibitors selected from butachlor, pretilachlor, mefenacet, s-metolachlor, flufenacet, pyroxasulfone and anilofos; (10) Lipid synthesis inhibitors (non-acetyl-CoA carboxylase): prosulfocarb; (11) A compound having the following formula: 【Chemistry 41】 a compound represented by the formula: embedded image and a synthetic hormone selected from fluroxypyr, florpyrauxifen benzyl, halaxifen methyl, triclopyr, clopyralid, picloram, aminopyralid, dicamba, 2-methyl-4-chlorophenoxyacetic acid and 2,4-dichlorophenoxyacetic acid; (12) EPSPS inhibitor: glyphosate; (13) A GS inhibitor selected from glufosinate ammonium and glufosinate-P-ammonium; (14) A PSI inhibitor selected from paraquat dichloride and diquat dibromide monohydrate; (15) a cellulose synthesis inhibitor selected from triaziflam and indaziflam; and (16) Other herbicides: Cinmethylin and one or more members selected from the group consisting of acids, salts and esters thereof.

11. The herbicidal composition comprises a herbicide having the following formula: 【Chemistry 42】 The herbicidal composition according to claim 10, comprising a compound represented by the formula:

12. 12. The herbicidal composition according to claim 10 or 11, characterized in that the herbicidal composition further comprises (iii) an agriculturally acceptable formulation adjuvant.

13. A method for controlling undesirable vegetation, characterized in that it comprises applying a herbicidally effective amount of at least one iminoaryl compound substituted with a carboxylic acid derivative according to any one of claims 1 to 7 or a herbicidal composition according to any one of claims 10 to 12 to a plant or its area or to the soil or water to control the germination or growth of the undesirable vegetation.

14. 14. The method of claim 13, wherein the undesirable vegetation comprises a herbicide resistant or tolerant weed species.

15. Use of at least one iminoaryl compound substituted with a carboxylic acid derivative according to any one of claims 1 to 7 or a herbicidal composition according to any one of claims 10 to 12 for controlling undesirable plants.

16. 16. The use according to claim 15, wherein the iminoaryl compounds substituted with carboxylic acid derivatives are used to control weeds in useful crops, the useful crops being genetically modified crops or crops treated with gene editing technology, and the weeds include herbicide-resistant or tolerant weed species.

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