Substituted pyrrolidone compounds, methods for preparing them, their compositions and applications

Abstract

The present invention belongs to the art of pesticides, and more particularly to substituted pyrrolidone compounds, methods for preparing the same, and their compositions and applications. The substituted pyrrolidone compounds are as shown in general formula I: JPEG2026510099000158.jpg39153 (In the formula, Q is, JPEG2026510099000159.jpg39153 represents; X and Y independently represent hydrogen, alkyl, alkenyl, alkynyl, etc.; Z represents alkyl, alkenyl, alkynyl, etc.; W1 and W2 independently represent O or S; R6 represents hydrogen, hydroxyl, halogen, etc.; R7 represents hydrogen, halogen, etc.; R8 represents hydrogen, alkyl, alkenyl, alkynyl, etc.). The compound has excellent herbicidal activity against grass weeds and other species, is safe, and has high selectivity for crops. In addition, it has good control activity against various fungi, such as tomato gray mold, rice sheath blight, and apple ring spot, as well as agricultural pests, such as lepidopteran insects (e.g., Spodoptera frugiperda, Mythimna separata).

Description

[Technical Field]

[0001] The present invention relates to the art of biological agents, and more particularly to substituted pyrrolidone compounds, methods for preparing the same, and compositions and applications thereof. [Background technology]

[0002] Weed control is one of the most important aspects in achieving highly efficient agriculture. While various herbicides are available on the market, the herbicidal properties of these known compounds against harmful plants and their selectivity for crops are not entirely satisfactory. Additionally, due to the continued expansion of the market, problems such as weed resistance, drug lifespan and cost-effectiveness, and increasing environmental awareness among people, scientists are expected to continuously research and further develop new, efficient, safe, and economical herbicide varieties with different modes of action. Furthermore, in recent years, the long-term use of pest control agents, such as insecticides or fungicides, has led to diseases and pests acquiring drug resistance, making them difficult to prevent or eliminate with currently used insecticides or fungicides. Moreover, some known pest control agents are highly toxic, or some damage ecosystems due to their long-term persistence. In this context, while numerous insecticides are known, there is still a need to develop new pest control agents with low toxicity and low persistence. [Overview of the project]

[0003] The present invention provides a substituted pyrrolidone compound, a method for preparing the same, and its compositions and applications. The compound has excellent herbicidal activity against gramineous weeds, etc., and is safe and has high selectivity for crops. In addition, it has good control activity against various fungi, such as tomato gray mold, sheath blight of rice, ring rot of apple, etc., and agricultural pests, such as lepidopteran insects (e.g., Spodoptera frugiperda, Mythimna separata, etc.).

[0004] The technical scheme adopted in the present invention is as follows: The substituted pyrrolidone compound is as shown in General Formula I: [Chemical formula] (In the formula, Q is [Chemical formula] represents; X and Y are each independently hydrogen, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, cycloalkyl, cycloalkylalkyl, aryl, arylalkyl, heterocyclyl, heterocyclylalkyl, hydroxyl, hydroxylalkyl, mercapto, mercaptoalkyl, nitro, cyanoalkyl, formyl, trialkylsilyl, -N(R , , 21 , 22 , 22 , 22 , 22 , 22 , , 21 , , 22 , 22 , 22 , 21 , 22 , 22 )2, -OR 22 , -SR<​​​​​​​​​​​​​​​​​​​​​22 , or -alkylene-(SO2)N(R 21 ) represents 2; Z is alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, cycloalkyl, cycloalkylalkyl, aryl, arylalkyl, heterocyclyl, heterocyclylalkyl, hydroxyl, hydroxylalkyl, mercapto, mercaptoalkyl, nitro, cyanoalkyl, formyl, trialkylsilyl, -N(R) 21 )2, -OR 22 , -SR 22 ,-(SO)R 22 ,-(CO)R 22 , -(CO)OR 22 ,-(SO2)R 22 ,-(SO2)N(R 21 )2,-alkylene-N(R 21 )2, -alkylene-OR 22 -Alkilen-SR 22 -Alkilen-(CO)R 22 -Alkilen-(CO)OR 22 -Alkilen-(SO2)R 22 , or -alkylene-(SO2)N(R 21 ) represents 2; W1 and W2 each independently represent either O or S; R6 represents hydrogen, hydroxyl, halogen, alkyl, cycloalkyl, alkoxy, or haloalkyl; R7 is hydrogen, halogen, nitro, cyano, formyl, carboxyl, hydroxyl, hydroxylalkyl, mercapto, mercaptoalkyl, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, -OR 22 , -SR 22 ,-(SO)R 22 ,-(SO2)R 22 ,-CR 23 =NOR 22 , -alkylene-OR 22 -Alkilen-SR 22 -Alkilen-(SO2)R 22, cycloalkyl, cycloalkenyl, aryl, heterocyclyl, -(CO)R 22 ,-(CO)N(R 21 )2, -(CO)OR 22 , -N(R 21 )2,-alkylene-(CO)R 22 -Alkylene-(CO)N(R 21 )2,-alkylene-(CO)OR 22 , or -alkylene-N(R 21 ) represents 2; R8 represents hydrogen, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, cycloalkyl, or cycloalkylalkyl; R1, R2, R3, R4, and R5 are each independently hydrogen, halogen, nitro, cyano, cyanothio, hydroxyl, mercapto, carboxyl, sulfo, formyl, haloformyl, azide, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, heterocyclyl, aryl, -N(R 21 )2, -(CO)N(R 21 )2, -O(CO)N(R 21 )2, -O(CS)N(R 21 )2, -(SO2)N(R 21 )2, -O(SO2)N(R 21 )2, -PO(OR 22 )2, -OR 22 ,-(CO)R 22 , -SR 22 ,-(SO)R 22 ,-(SO2)R 22 , -Si(R 22 )3, -O(CO)R 22 ,-O-(SO2)R 22 ,-S(CO)R 22 , -(SO2)OR 22 , -O(CO)OR 22 , -(CO)(CO)OR 22 , -(CO)OR 22 -ON=C(R 23 )2, -CR 23 =N-OH, or -CR 23 =NOR 22represents; "alkyl", "alkenyl" or "alkynyl" is halogen, nitro, cyano, hydroxyl, mercapto, carboxyl, cycloalkyl, cycloalkenyl, heterocyclyl, aryl, -N(R 21 )2, -(CO)N(R 21 )2, -O(CO)N(R 21 )2, -O(CS)N(R 21 )2, -(SO2)N(R 21 )2, -O(SO2)N(R 21 )2, -OR 22 , -(CO)R 22 , -SR 22 , -(SO)R 22 , -(SO2)R 22 , -O(CO)H, -O(CO)R 22 , -O-(SO2)R 22 , -(CO)OR 22 , -O(CO)OR 22 , -Si(R 22 )3, -O(CO)(CO)OH, -O(CO)(CO)OR 22 , -O-alkylene-(CO)OH, and -O-alkylene-(CO)OR 22 may be substituted by at least one group selected from; R 11 are each independently halogen, nitro, cyano, cyanothio, hydroxyl, mercapto, carboxyl, sulfo, formyl, haloformyl, azide, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, heterocyclyl, aryl, -N(R 21 )2, -(CO)N(R 21 )2, -O(CO)N(R 21 )2, -O(CS)N(R 21 )2, -(SO2)N(R 21 )2, -O(SO2)N(R 21 )2, -PO(OR 22 )2, -OR 22 , -(CO)R 22 , -SR 22 , -(SO)R 22 , -(SO2)R 22 , -Si(R 22 )3, -O(CO)R22 ,-O-(SO2)R 22 ,-S(CO)R 22 , -(SO2)OR 22 , -O(CO)OR 22 , -(CO)(CO)OR 22 , -(CO)OR 22 -ON=C(R 23 )2, -CR 23 =N-OH, or -CR 23 =NOR 22 "Alkyl," "alkenyl," or "alkynyl" are derived from halogens, nitro, cyano, hydroxyl, mercapto, carboxyl, cycloalkyl, cycloalkenyl, heterocyclyl, aryl, and -N(R) 21 )2, -(CO)N(R 21 )2, -O(CO)N(R 21 )2, -O(CS)N(R 21 )2, -(SO2)N(R 21 )2, -O(SO2)N(R 21 )2, -OR 22 ,-(CO)R 22 , -SR 22 ,-(SO)R 22 ,-(SO2)R 22 -O(CO)H, -O(CO)R 22 ,-O-(SO2)R 22 , -(CO)OR 22 , -O(CO)OR 22 , -Si(R 22 )3, -O(CO)(CO)OH, -O(CO)(CO)OR 22 -O-alkylene-(CO)OH, and -O-alkylene-(CO)OR 22 It may be replaced by at least one element selected from; R 21 Each of these is independently hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, aryl, heterocyclyl, -OR 22 ,-(CO)R 22 , -(CO)OR 22 -Alkilen-(CO)OR 22 ,-(SO2)R 22 , -(SO2)OR22 -Alkilen-(SO2)R 22 ,-(CO)N(R 24 )2, or -(SO2)N(R 24 ) represents 2; R 22 Each of these independently represents alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, aryl, or heterocyclyl, where "alkyl", "alkenyl", or "alkynyl" are halogen, cyano, trialkylsilyl, cycloalkyl, cycloalkenyl, aryl, heterocyclyl, -OR 25 , -SR 25 ,-O(CO)R 25 ,-(CO)R 25 , -(CO)OR 25 , and -O(CO)OR 25 It may be replaced by at least one element selected from; R 23 Each of these independently represents hydrogen, halogen, alkoxy, alkoxyalkyl, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl, cycloalkenylalkyl, aryl, arylalkyl, heterocyclyl, or heterocyclylalkyl; R 24 Each of these independently represents hydrogen, alkyl, alkenyl, alkynyl, alkoxy, alkylsulfonyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl, or cycloalkenylalkyl; or N(R 21 )2 and N(R 24 )2 each independently represents a heterocyclyl having a nitrogen atom at position 1; R 25Each independently represents hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, haloalkyl, haloalkenyl, haloalkynyl, phenyl, or: halogen, cyano, nitro, alkyl, haloalkyl, alkoxy, haloalkoxy, alkoxycarbonyl, alkylthio, alkylsulfonyl, phenoxy, and phenyl substituted with at least one group selected from halogen, cyano, nitro, alkyl, haloalkyl, alkoxy, and haloalkoxy; The above terms "cycloalkyl," "cycloalkenyl," "heterocyclyl," or "aryl" include oxo, halogen, cyano, nitro, alkyl, alkenyl, alkynyl, cycloalkyl, haloalkyl, haloalkenyl, haloalkynyl, halocycloalkyl, alkyl-substituted cycloalkyl, -OR 10 , -SR 10 , -(CO)OR 10 ,-(SO2)R 10 , -N(R 10 )2 and -O-alkylene-(CO)OR 10 It may be substituted with at least one group selected from, or two adjacent carbon atoms may form a fused ring with unsubstituted or halogen-substituted -OCH2CH2- or -OCH2O-; R 10 Each of these independently represents a phenyl molecule substituted with hydrogen, alkyl, haloalkyl, phenyl, or at least one group selected from halogen, cyano, nitro, alkyl, haloalkyl, alkoxycarbonyl, alkylthio, alkylsulfonyl, alkoxy, and haloalkoxy.

[0005] Preferably, X and Y are each independently hydrogen, 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, aryl, aryl-C1-C8 alkyl, heterocyclyl, heterocyclyl-C1-C8 alkyl, hydroxyl, hydroxyl-C1-C8 alkyl, mercapto, mercapto-C1-C8 alkyl, nitro, cyano-C1-C8 alkyl, formyl, tri-C1-C8 alkylsilyl, -N(R) 21 )2, -OR 22 , -SR 22 ,-(SO)R 22 ,-(CO)R 22 , -(CO)OR 22 ,-(SO2)R 22 ,-(SO2)N(R 21 )2,-(C1-C8 alkylene)-N(R 21 )2, -(C1-C8 alkylene)-OR 22 ,-(C1-C8 Alkilen)-SR 22 -(C1-C8 alkylene)-(CO)R 22 -(C1-C8 alkylene)-(CO)OR 22 -(C1-C8 Alkylene)-(SO2)R 22 , or -(C1-C8 alkylene)-(SO2)N(R 21 ) represents 2; Z is 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, aryl, aryl-C1-C8 alkyl, heterocyclyl, heterocyclyl-C1-C8 alkyl, hydroxyl, hydroxyl-C1-C8 alkyl, mercapto, mercapto-C1-C8 alkyl, nitro, cyano-C1-C8 alkyl, formyl, tri-C1-C8 alkylsilyl, -N(R 21 )2, -OR 22 , -SR 22 ,-(SO)R 22 ,-(CO)R 22 , -(CO)OR22 ,-(SO2)R 22 ,-(SO2)N(R 21 )2,-(C1-C8 alkylene)-N(R 21 )2, -(C1-C8 alkylene)-OR 22 ,-(C1-C8 Alkilen)-SR 22 -(C1-C8 alkylene)-(CO)R 22 -(C1-C8 alkylene)-(CO)OR 22 -(C1-C8 Alkylene)-(SO2)R 22 , or -(C1-C8 alkylene)-(SO2)N(R 21 ) represents 2; R6 represents hydrogen, hydroxyl, halogen, C1-C8 alkyl, C3-C8 cycloalkyl, C1-C8 alkoxy, or halo-C1-C8 alkyl; R7 is hydrogen, halogen, nitro, cyano, formyl, carboxyl, hydroxyl, hydroxyl C1-C8 alkyl, mercapto, mercapto C1-C8 alkyl, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, halo C1-C8 alkyl, halo C2-C8 alkenyl, halo C2-C8 alkynyl, -OR 22 , -SR 22 ,-(SO)R 22 ,-(SO2)R 22 ,-CR 23 =NOR 22 ,-(C1-C8 alkylene)-OR 22 ,-(C1-C8 Alkilen)-SR 22 -(C1-C8 Alkylene)-(SO2)R 22 C3-C8 cycloalkyl, C3-C8 cycloalkenyl, aryl, heterocyclyl, -(CO)R 22 ,-(CO)N(R 21 )2, -(CO)OR 22 , -N(R 21 )2,-(C1-C8 alkylene)-(CO)R 22 -(C1-C8 alkylene)-(CO)N(R) 21 )2, -(C1-C8 alkylene)-(CO)OR 22 , or -(C1-C8 alkylene)-N(R21 ) represents 2; R8 represents hydrogen, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, halo-C1-C8 alkyl, halo-C2-C8 alkenyl, halo-C2-C8 alkynyl, C3-C8 cycloalkyl, or C3-C8 cycloalkyl-C1-C8 alkyl; R1, R2, R3, R4, and R5 are each independently hydrogen, halogen, nitro, cyano, cyanothio, hydroxyl, mercapto, carboxyl, sulfo, formyl, haloformyl, azide, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkenyl, heterocyclyl, aryl, -N(R 21 )2, -(CO)N(R 21 )2, -O(CO)N(R 21 )2, -O(CS)N(R 21 )2, -(SO2)N(R 21 )2, -O(SO2)N(R 21 )2, -PO(OR 22 )2, -OR 22 ,-(CO)R 22 , -SR 22 ,-(SO)R 22 ,-(SO2)R 22 , -Si(R 22 )3, -O(CO)R 22 ,-O-(SO2)R 22 ,-S(CO)R 22 , -(SO2)OR 22 , -O(CO)OR 22 , -(CO)(CO)OR 22 , -(CO)OR 22 -ON=C(R 23 )2, -CR 23 =N-OH, or -CR 23 =NOR 22 Represents; "C1-C8 alkyl", "C2-C8 alkenyl", or "C2-C8 alkynyl" are halogen, nitro, cyano, hydroxyl, mercapto, carboxyl, C3-C8 cycloalkyl, C3-C8 cycloalkenyl, heterocyclyl, aryl, -N(R) 21 )2, -(CO)N(R 21)2, -O(CO)N(R 21 )2, -O(CS)N(R 21 )2, -(SO2)N(R 21 )2, -O(SO2)N(R 21 )2, -OR 22 ,-(CO)R 22 , -SR 22 ,-(SO)R 22 ,-(SO2)R 22 -O(CO)H, -O(CO)R 22 ,-O-(SO2)R 22 , -(CO)OR 22 , -O(CO)OR 22 , -Si(R 22 )3, -O(CO)(CO)OH, -O(CO)(CO)OR 22 -O-(C1-C8 alkylene)-(CO)OH, and -O-(C1-C8 alkylene)-(CO)OR 22 It may be replaced by at least one element selected from; R 11 These are, independently, halogen, nitro, cyano, cyanothio, hydroxyl, mercapto, carboxyl, sulfo, formyl, haloformyl, azide, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkenyl, heterocyclyl, aryl, -N(R) 21 )2, -(CO)N(R 21 )2, -O(CO)N(R 21 )2, -O(CS)N(R 21 )2, -(SO2)N(R 21 )2, -O(SO2)N(R 21 )2, -PO(OR 22 )2, -OR 22 ,-(CO)R 22 , -SR 22 ,-(SO)R 22 ,-(SO2)R 22 , -Si(R 22 )3, -O(CO)R 22 ,-O-(SO2)R 22 ,-S(CO)R 22 , -(SO2)OR 22 , -O(CO)OR 22, -(CO)(CO)OR 22 , -(CO)OR 22 -ON=C(R 23 )2, -CR 23 =N-OH, or -CR 23 =NOR 22 Represents; "C1-C8 alkyl", "C2-C8 alkenyl", or "C2-C8 alkynyl" are halogen, nitro, cyano, hydroxyl, mercapto, carboxyl, C3-C8 cycloalkyl, C3-C8 cycloalkenyl, heterocyclyl, aryl, -N(R) 21 )2, -(CO)N(R 21 )2, -O(CO)N(R 21 )2, -O(CS)N(R 21 )2, -(SO2)N(R 21 )2, -O(SO2)N(R 21 )2, -OR 22 ,-(CO)R 22 , -SR 22 ,-(SO)R 22 ,-(SO2)R 22 -O(CO)H, -O(CO)R 22 ,-O-(SO2)R 22 , -(CO)OR 22 , -O(CO)OR 22 , -Si(R 22 )3, -O(CO)(CO)OH, -O(CO)(CO)OR 22 -O-(C1-C8 alkylene)-(CO)OH, and -O-(C1-C8 alkylene)-(CO)OR 22 It may be replaced by at least one element selected from; R 21 Each of these is independently hydrogen, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkenyl, aryl, heterocyclyl, -OR 22 ,-(CO)R 22 , -(CO)OR 22 -(C1-C8 alkylene)-(CO)OR 22 ,-(SO2)R 22 , -(SO2)OR 22 -(C1-C8 Alkylene)-(SO2)R22 ,-(CO)N(R 24 )2, or -(SO2)N(R 24 ) represents 2; R 22 Each of these independently represents a C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkenyl, aryl, or heterocyclyl, where "C1-C8 alkyl", "C2-C8 alkenyl", or "C2-C8 alkynyl" are halogens, cyano, tri-C1-C8 alkylsilyl, C3-C8 cycloalkyl, C3-C8 cycloalkenyl, aryl, heterocyclyl, -OR 25 , -SR 25 ,-O(CO)R 25 ,-(CO)R 25 ,-(CO)OR 25 , and -O(CO)OR 25 It may be replaced by at least one element selected from; R 23 Each of these independently represents hydrogen, halogen, C1-C8 alkoxy, C1-C8 alkoxy C1-C8 alkyl, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkyl C1-C8 alkyl, C3-C8 cycloalkenyl, C3-C8 cycloalkenyl C1-C8 alkyl, aryl, aryl C1-C8 alkyl, heterocyclyl, or heterocyclyl C1-C8 alkyl; R 24 Each independently represents hydrogen, 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 N(R 21 )2 and N(R 24 )2 each independently represents a heterocyclyl having a nitrogen atom at position 1; R 25Each independently represents hydrogen, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, halo-C1-C8 alkyl, halo-C2-C8 alkenyl, halo-C2-C8 alkynyl, phenyl, or: halogen, cyano, nitro, C1-C8 alkyl, halo-C1-C8 alkyl, C1-C8 alkoxy, halo-C1-C8 alkoxy, C1-C8 alkoxycarbonyl, C1-C8 alkylthio, C1-C8 alkylsulfonyl, phenoxy, and phenyl substituted with at least one group selected from halogen, cyano, nitro, C1-C8 alkyl, halo-C1-C8 alkyl, C1-C8 alkoxy, and halo-C1-C8 alkoxy; The above "C3-C8 cycloalkyl", "C3-C8 cycloalkenyl", "heterocyclyl", or "aryl" are 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 10 , -SR 10 , -(CO)OR 10 ,-(SO2)R 10 , -N(R 10 )2 and -O-(C1-C8 alkylene)-(CO)OR 10 It may be substituted with at least one group selected from, or two adjacent carbon atoms may form a fused ring with unsubstituted or halogen-substituted -OCH2CH2- or -OCH2O-; R 10 Each of these independently represents hydrogen, 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).

[0006] More preferably, X and Y are independently hydrogen, 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, aryl, aryl-C1-C6 alkyl, heterocyclyl, heterocyclyl-C1-C6 alkyl, hydroxyl, hydroxyl-C1-C6 alkyl, mercapto, mercapto-C1-C6 alkyl, nitro, cyano-C1-C6 alkyl, formyl, tri-C1-C6 alkylsilyl, -N(R) 21 )2, -OR 22 , -SR 22 ,-(SO)R 22 ,-(CO)R 22 , -(CO)OR 22 ,-(SO2)R 22 ,-(SO2)N(R 21 )2,-(C1-C6 alkylene)-N(R 21 )2, -(C1-C6 alkylene)-OR 22 ,-(C1-C6 Alkilen)-SR 22 -(C1-C6 alkylene)-(CO)R 22 -(C1-C6 alkylene)-(CO)OR 22 -(C1-C6 alkylene)-(SO2)R 22 , or -(C1-C6 alkylene)-(SO2)N(R 21 ) represents 2; Z is 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, aryl, aryl-C1-C6 alkyl, heterocyclyl, heterocyclyl-C1-C6 alkyl, hydroxyl, hydroxyl-C1-C6 alkyl, mercapto, mercapto-C1-C6 alkyl, nitro, cyano-C1-C6 alkyl, formyl, tri-C1-C6 alkylsilyl, -N(R 21 )2, -OR 22 , -SR 22 ,-(SO)R22 ,-(CO)R 22 , -(CO)OR 22 ,-(SO2)R 22 ,-(SO2)N(R 21 )2,-(C1-C6 alkylene)-N(R 21 )2, -(C1-C6 alkylene)-OR 22 ,-(C1-C6 Alkilen)-SR 22 -(C1-C6 alkylene)-(CO)R 22 -(C1-C6 alkylene)-(CO)OR 22 -(C1-C6 alkylene)-(SO2)R 22 , or -(C1-C6 alkylene)-(SO2)N(R 21 ) represents 2; R6 represents hydrogen, hydroxyl, halogen, C1-C6 alkyl, C3-C6 cycloalkyl, C1-C6 alkoxy, or halo-C1-C6 alkyl; R7 is hydrogen, halogen, nitro, cyano, formyl, carboxyl, hydroxyl, hydroxyl C1-C6 alkyl, mercapto, mercapto C1-C6 alkyl, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, halo C1-C6 alkyl, halo C2-C6 alkenyl, halo C2-C6 alkynyl, -OR 22 , -SR 22 ,-(SO)R 22 ,-(SO2)R 22 ,-CR 23 =NOR 22 ,-(C1-C6 alkylene)-OR 22 ,-(C1-C6 Alkilen)-SR 22 -(C1-C6 alkylene)-(SO2)R 22 C3-C6 cycloalkyl, C3-C6 cycloalkenyl, aryl, heterocyclyl, -(CO)R 22 ,-(CO)N(R 21 )2, -(CO)OR 22 , -N(R 21 )2,-(C1-C6 alkylene)-(CO)R 22 -(C1-C6 alkylene)-(CO)N(R) 21 )2, -(C1-C6 alkylene)-(CO)OR22 , or -(C1-C6 alkylene)-N(R 21 ) represents 2; R8 represents hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, halo-C1-C6 alkyl, halo-C2-C6 alkenyl, halo-C2-C6 alkynyl, C3-C6 cycloalkyl, or C3-C6 cycloalkyl-C1-C6 alkyl; R1, R2, R3, R4, and R5 are each independently hydrogen, halogen, nitro, cyano, cyanothio, hydroxyl, mercapto, carboxyl, sulfo, formyl, haloformyl, azide, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkenyl, heterocyclyl, aryl, -N(R 21 )2, -(CO)N(R 21 )2, -O(CO)N(R 21 )2, -O(CS)N(R 21 )2, -(SO2)N(R 21 )2, -O(SO2)N(R 21 )2, -PO(OR 22 )2, -OR 22 ,-(CO)R 22 , -SR 22 ,-(SO)R 22 ,-(SO2)R 22 , -Si(R 22 )3, -O(CO)R 22 ,-O-(SO2)R 22 ,-S(CO)R 22 , -(SO2)OR 22 , -O(CO)OR 22 , -(CO)(CO)OR 22 , -(CO)OR 22 -ON=C(R 23 )2, -CR 23 =N-OH, or -CR 23 =NOR 22 Represents; "C1-C6 alkyl", "C2-C6 alkenyl", or "C2-C6 alkynyl" are halogens, nitro, cyano, hydroxyl, mercapto, carboxyl, C3-C6 cycloalkyl, C3-C6 cycloalkenyl, heterocyclyl, aryl, -N(R)21 )2, -(CO)N(R 21 )2, -O(CO)N(R 21 )2, -O(CS)N(R 21 )2, -(SO2)N(R 21 )2, -O(SO2)N(R 21 )2, -OR 22 ,-(CO)R 22 , -SR 22 ,-(SO)R 22 ,-(SO2)R 22 -O(CO)H, -O(CO)R 22 ,-O-(SO2)R 22 , -(CO)OR 22 , -O(CO)OR 22 , -Si(R 22 )3, -O(CO)(CO)OH, -O(CO)(CO)OR 22 -O-(C1-C6 alkylene)-(CO)OH, and -O-(C1-C6 alkylene)-(CO)OR 22 It may be replaced by at least one element selected from; R 11 These are, independently, halogen, nitro, cyano, cyanothio, hydroxyl, mercapto, carboxyl, sulfo, formyl, haloformyl, azide, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkenyl, heterocyclyl, aryl, -N(R) 21 )2, -(CO)N(R 21 )2, -O(CO)N(R 21 )2, -O(CS)N(R 21 )2, -(SO2)N(R 21 )2, -O(SO2)N(R 21 )2, -PO(OR 22 )2, -OR 22 ,-(CO)R 22 , -SR 22 ,-(SO)R 22 ,-(SO2)R 22 , -Si(R 22 )3, -O(CO)R 22 ,-O-(SO2)R 22 ,-S(CO)R 22, -(SO2)OR 22 , -O(CO)OR 22 , -(CO)(CO)OR 22 , -(CO)OR 22 -ON=C(R 23 )2, -CR 23 =N-OH, or -CR 23 =NOR 22 Represents; "C1-C6 alkyl", "C2-C6 alkenyl", or "C2-C6 alkynyl" are halogens, nitro, cyano, hydroxyl, mercapto, carboxyl, C3-C6 cycloalkyl, C3-C6 cycloalkenyl, heterocyclyl, aryl, -N(R) 21 )2, -(CO)N(R 21 )2, -O(CO)N(R 21 )2, -O(CS)N(R 21 )2, -(SO2)N(R 21 )2, -O(SO2)N(R 21 )2, -OR 22 ,-(CO)R 22 , -SR 22 ,-(SO)R 22 ,-(SO2)R 22 -O(CO)H, -O(CO)R 22 ,-O-(SO2)R 22 , -(CO)OR 22 , -O(CO)OR 22 , -Si(R 22 )3, -O(CO)(CO)OH, -O(CO)(CO)OR 22 -O-(C1-C6 alkylene)-(CO)OH, and -O-(C1-C6 alkylene)-(CO)OR 22 It may be replaced by at least one element selected from; R 21 These are, independently, hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkenyl, aryl, heterocyclyl, -OR 22 ,-(CO)R 22 , -(CO)OR 22 -(C1-C6 alkylene)-(CO)OR 22 ,-(SO2)R 22, -(SO2)OR 22 -(C1-C6 alkylene)-(SO2)R 22 ,-(CO)N(R 24 )2, or -(SO2)N(R 24 ) represents 2; R 22 Each of these independently represents a C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkenyl, aryl, or heterocyclyl, where "C1-C6 alkyl", "C2-C6 alkenyl", or "C2-C6 alkynyl" are halogens, cyano, triC1-C6 alkylsilyl, C3-C6 cycloalkyl, C3-C6 cycloalkenyl, aryl, heterocyclyl, -OR 25 , -SR 25 ,-O(CO)R 25 ,-(CO)R 25 , -(CO)OR 25 , and -O(CO)OR 25 It may be replaced by at least one element selected from; R 23 Each of these independently represents hydrogen, halogen, C1-C6 alkoxy, C1-C6 alkoxy C1-C6 alkyl, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C6 alkyl, C3-C6 cycloalkenyl, C3-C6 cycloalkenyl C1-C6 alkyl, aryl, aryl C1-C6 alkyl, heterocyclyl, or heterocyclyl C1-C6 alkyl; R 24 Each independently represents hydrogen, 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 N(R 21 )2 and N(R 24)2 is independently either unsubstituted or substituted with at least one group selected from oxo, C1-C6 alkyl, and C1-C6 alkoxycarbonyl groups. [ka] It represents; R 25 Each independently represents a phenyl substituted with at least one group selected from hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, halo-C1-C6 alkyl, halo-C2-C6 alkenyl, halo-C2-C6 alkynyl, phenyl, or: halogen, cyano, nitro, C1-C6 alkyl, halo-C1-C6 alkyl, C1-C6 alkoxy, halo-C1-C6 alkoxy, C1-C6 alkoxycarbonyl, C1-C6 alkylthio, C1-C6 alkylsulfonyl, phenoxy, and phenyl substituted with at least one group selected from halogen, cyano, nitro, C1-C6 alkyl, halo-C1-C6 alkyl, C1-C6 alkoxy, and halo-C1-C6 alkoxy; The above terms "C3-C6 cycloalkyl", "C3-C6 cycloalkenyl", "heterocyclyl", or "aryl" include 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 10 , -SR 10 , -(CO)OR 10 ,-(SO2)R 10 , -N(R 10 )2 and -O-(C1-C6 alkylene)-(CO)OR 10 It may be substituted with at least one group selected from, or two adjacent carbon atoms may form a fused ring with unsubstituted or halogen-substituted -OCH2CH2- or -OCH2O-; R 10Each independently represents hydrogen, C1-C6 alkyl, halo-C1-C6 alkyl, phenyl, or phenyl substituted with at least one group 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.

[0007] In the definition of compounds represented by the above general formula and all of the following structural formulas, the technical terms used, whether used alone or in the compound name, represent the following substituents: alkyl groups having two or more carbon atoms and which may be linear or branched. For example, the compound name "-alkylene-(CO)OR 22The alkylene in " may be -CH2-, -CH2CH2-, -CH(CH3)-, -C(CH3)2-, etc. The alkyl group 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, the alkenyl is, for example, vinyl, allyl, 1-methylpropa-2-en-1-yl, 2-methylpropa-2-en-1-yl, buta-2-en-1-yl, buta-3-en-1-yl, 1-methylbuta-3-en-1-yl, or 1-methylbuta-2-en-1-yl. Alkynnyls are, for example, ethinyl, propargyl, buta-2-in-1-yl, buta-3-in-1-yl, or 1-methylbuta-3-in-1-yl. Multiple bonds may be at any position on each unsaturated group. Cycloalkyls are, for example, saturated carbocyclic ring systems having 3 to 6 carbon atoms, such as cyclopropyl, cyclobutyl, cyclopentyl, or cyclohexyl. Similarly, cycloalkenyls are, for example, monocyclic alkenyls having 3 to 6 carbon ring members, such as cyclopropenyl, cyclobutenyl, cyclopentenyl, or cyclohexenyl, where the double bond can be at any position. Halogens are fluorine, chlorine, bromine, or iodine.

[0008] Unless otherwise specified, the “aryl” in this invention refers to phenyl, naphthyl, [ka] This includes, but is not limited to; "heterocyclyl" refers to a saturated or unsaturated non-aromatic cyclic group [ka] This includes, but is not limited to, heteroaryl aromatic cyclic groups having, for example, 3 to 6 ring atoms and which may also be fused with a benzo ring. The 1 to 4 (e.g., 1, 2, 3, or 4) heteroatoms of the ring atom are selected from oxygen, nitrogen, and sulfur, for example, [ka] That is the case.

[0009] When one group is substituted by another group, it should be understood that this means the group is substituted by one or more identical or different groups selected from the described groups. Additionally, identical or different substitutional features contained within identical or different substituents may be independently selected and identical or different. This is also applicable to ring systems formed by different atoms and units. On the other hand, the scope of the claims excludes compounds that are chemically unstable under standard conditions known to those skilled in the art.

[0010] Additionally, unless otherwise defined, the term “substituted by at least one group” in this specification means substituted by, for example, one, two, three, four, or five groups; groups whose linkage sites are not specified (including heterocyclyls, aryls, etc.) may be linked at any site, including sites linked to C or N; and if substituted, substituents may also be substituted at any site, insofar as they conform to valence bond theory. For example, a heteroaryl substituted by one methyl group. [ka] teeth, [ka] It can also represent things like that.

[0011] The present invention provides substituted pyrrolidone compounds having a chiral center represented by formula I': [ka] (In the formula, the definitions of substituents Q, R6, R7, R8, W1, W2, X, Y, and Z are as described above.)

[0012] In one particular embodiment, the stereochemical purity is 60% to 100% (S), preferably 70% to 100%, more preferably 80% to 100%, even more preferably 90% to 100%, and even more preferably 95% to 100%, based on the content of stereoisomers having R and S configurations at the 3-position; and also 60% to 100% (S or R, depending on the type of substituent Q), preferably 70% to 100%, more preferably 80% to 100%, even more preferably 90% to 100%, and even more preferably 95% to 100%, based on the content of stereoisomers having R and S configurations at the 4-position.

[0013] In these contexts, "stereochemical purity" refers to the percentage of the amount of stereoisomers relative to the total amount of stereoisomers containing chiral centers.

[0014] In the present invention, the stereochemical configurations at positions 3 and 4 in formula I' are determined according to the Cahn-Ingold-Prelogue system, respectively. However, the subject matter of the present invention also relates to all stereoisomers at other positions encompassed by formulas I and I', as well as mixtures thereof. Such compounds of formulas I and I' contain, for example, one or more additional chiral carbon atoms or other double bonds not specified in formulas I and I'. It should be understood that the present invention comprises pure isomers and mixtures of pure isomers concentrated to a variable degree, where the chiral carbon atom at the labeled 3 position is in the S configuration, and the chiral carbon atom at the labeled 4 position is in the S or R configuration; or in a mixture, a compound or a compound of the same chemical structure has the configuration at the labeled position, or is present in proportion such that compounds having the configuration are predominant (at least 60% have the configuration); on the other hand, other chiral carbon atoms may be present in racemic form or separated to a variable degree. As long as the stereochemical configuration at the labeled position is suitable, all possible stereoisomers defined by their specific spatial configuration, such as enantiomers, diastereoisomers, Z and E isomers, are included in formulas I and I', and may be obtained from mixtures of stereoisomers using conventional methods, or prepared by stereoselective reactions in combination with the use of stereochemically pure starting materials.

[0015] The present invention also includes any keto-enol tautomer forms, mixtures thereof, and salts, in the presence of various functional groups.

[0016] Stereoiomers can be obtained from prepared mixtures by optical separation. Stereoiomers may also be selectively prepared by using stereoselective reactions and optically active starting materials and / or auxiliary agents. Conventional methods can often be used for optical separation (see Textbooks of Stereochemistry), which include, for example, the methods described below for separating mixtures into diastereoisomers, such as physical methods, e.g., crystallization, chromatography, especially column chromatography and high-pressure liquid chromatography, distillation methods performed under reduced pressure if necessary, extraction, and other methods. Chromatographic separation on a chiral solid phase is commonly employed to separate residual mixtures of enantiomers. Suitable for preparatory quantities or for industrial-scale use are methods such as crystallization of diastereomer salts, which can be obtained from compounds using optically active acids, and optically active bases can be used as needed if acidic groups are present.

[0017] The method for preparing the substituted pyrrolidone compound includes the following steps: [ka] (In the formula, M represents OH or halogen, and the definitions of substituents Q, R6, R7, R8, W1, W2, X, Y, and Z are as described above.)

[0018] Preferably, the reaction is carried out in the presence of a solvent; more preferably, a coupling agent and / or a base is added during the reaction.

[0019] In one particular embodiment, the base is selected from at least one of inorganic bases (e.g., K2CO3, Na2CO3, Cs2CO3, NaHCO3, KHCO3, KF, CsF, KI, NaI, K3PO4, K2HPO4, NaOH, KOH, NaH, KH, etc.) and organic bases (e.g., DMAP, pyrazole, triethylamine, DIEA, potassium trimethylsilanolate, AcOK, AcONa, MeONa, EtONa, t-BuONa, etc.).

[0020] In one particular embodiment, the solvent is selected from at least one of DMF, DMA, methanol, ethanol, acetonitrile, dichloroethane, DMSO, dioxane, dichloromethane (DCM), and ethyl acetate.

[0021] In one particular embodiment, the coupling agent is selected from at least one of Py-BOP, Py-AOP, EDCI, HOBT (1-hydroxybenzotriazole), DCC, HBTU, and HATU.

[0022] Additionally, compounds represented by general formula I can be prepared by referring to the methods described in International Publication No. 2016196593, International Publication No. 2015084796, Chinese Patent No. 115504920, and others.

[0023] The intermediate is as shown in Equation II or Equation III above.

[0024] The herbicidal composition comprises at least one substituted pyrrolidone compound in an effectively herbicidal amount, and preferably also comprises a formulation aid.

[0025] A method for controlling weeds comprises applying at least one substituted pyrrolidone compound or herbicidal composition in a herbicidally effective amount to a plant or weed plot.

[0026] At least one of the substituted pyrrolidone compounds or herbicidal compositions has an application in weed control; preferably, the substituted pyrrolidone compound is used to prevent or eliminate weeds among useful crops, and the useful crops are transgenic crops or crops treated with genome editing technology.

[0027] The compounds of formula I or I' of the present invention have outstanding herbicidal activity against a wide range of economically important monocotyledonous and dicotyledonous weeds. The active substances of the present invention also act effectively on perennial weeds that grow from rootstock, rhizomes, or other perennial organs and are difficult to control. In this context, it is generally not important whether the substance is applied before sowing, before emergence, or after emergence. Representative examples of monocotyledonous and dicotyledonous weed plants that can be controlled by the compounds of the present invention can be described in detail without limiting them to any particular species. Examples of weed species in which the active substance acts efficiently include monocots such as the annuals Avena, Lolium, Alopecurus, Phalaris, Echinochloa, Digitalia, Setaria, and Cyperus, as well as the perennials Agropyron, Cynodon, Imperata, and Sorghum, and the perennial Cyperus.

[0028] In the case of dicotyledonous weed species, the range of action extends to annuals such as gallium, viola, veronica, lamium, stellaria, amaranth, synapse, ipomoea, ferns, matricaria, and abutilon, as well as perennial weeds such as convolvulus, cirsium, rumex, and artemisia. The active substance of the present invention effectively controls harmful plants, such as Echinochloa, Sagittaria, Alisma, Eleocharis, Scirpus, and Cyperus, under specific conditions of rice growth. When the compound of the present invention is applied to the soil surface prior to germination, weed seedlings are completely prevented from emerging, or the weeds stop growing when they reach the cotyledon stage and eventually die completely after 3-4 weeks. In particular, the compounds of the present invention exhibit excellent activity against Apera spica venti, Matsumurella chinense, Fallopia convolvulus, Stellaria media, Veronica hederifolia, Veronica persica, Viola tricolor, Amaranthus, Gallium, and Kochia.

[0029] The compounds of the present invention exhibit excellent herbicidal activity against monocotyledonous and dicotyledonous weeds, while causing little to no damage to economically important crop plants such as wheat, barley, rye, rice, maize, sugar beet, cotton, and soybean. In particular, they have excellent compatibility with cereals such as wheat, barley, and maize, especially wheat. Therefore, the compounds of the present invention are very suitable for selectively controlling undesirable plants in plantings for agricultural or decorative use.

[0030] Due to their herbicidal properties, these active substances may be used to control harmful plants in the planting of known or introduced genetically modified plants. Transgenic plants typically possess advantageous traits, such as resistance to certain pesticides, particularly certain herbicides; and resistance to plant diseases or pathogenic microorganisms of plant diseases, such as certain insects or microorganisms including fungi, bacteria, or viruses. Other distinctive traits relate to the following aspects of the product, such as quantity, quality, storage stability, composition, and special components. Thus, the resulting transgenic plant products are known to have increased starch content, or modified starch quality, or different fatty acid composition.

[0031] The compounds of formula I or I' of the present invention, or salts thereof, are preferably used in the planting of economically important transgenic crops and ornamental plants, such as grains, such as wheat, barley, rye, oats, millet, rice, manioc, and maize; or in the planting of vegetable plants, such as sugar beets, cotton, soybeans, rapeseed, potatoes, tomatoes, and peas. The compounds of formula I or I' are preferably used as herbicides in the planting of useful plants that are resistant to the toxic effects of herbicides or have been made resistant by genetic engineering.

[0032] Conventional methods for crossbreeding plants with modified traits compared to known plants include, for example, conventional crossbreeding methods and crossbreeding of mutant varieties. In other words, novel plants with improved traits may be produced with the aid of genetic engineering methods (see, for example, European Patent No. 0221044 and European Patent No. 0131624). For example, several methods are described: - Modification of crop plants by altering starch synthesis in plants using genetic engineering (e.g., International Publication No. 92 / 11376, International Publication No. 92 / 14827, International Publication No. 91 / 19806); - Transgenic crop plants resistant to certain herbicides, including glufosinate herbicides (e.g., European Patent No. 0242236, European Patent No. 0242246), glyphosate herbicides (International Publication No. 92 / 00377), or sulfonylurea herbicides (European Patent No. 0257993, U.S. Patent No. 5013659); - Transgenic crop plants capable of producing Bacillus thuringiensis toxin (Bt toxin), which confers resistance to certain pests that infect plants, such as cotton (European Patent No. 0142924, European Patent No. 0193259); - Transgenic crop plants with altered fatty acid composition (International Publication No. 91 / 13972).

[0033] Numerous molecular biology techniques are known that enable the preparation of transgenic plants with modified traits (e.g., Sambrook et al., 1989, Molecular Cloning, A Laboratory Manual, 2) nd edition, Cold Spring Harbor Laboratory Press, Cold Spring Harbor, NY; or Winnacker, “Gene und Klone” [Genes and Clones], VCH Weinheim, 2 nd(See edition, 1996; or Christou, “Trends in Plant Science”, 1 (1996) 423–431). To perform genetic manipulation, nucleic acid molecules can be introduced into plasmids to induce mutagenesis or sequence changes through DNA sequence recombination. Using the standard processes described above, for example, base substitutions, partial sequence removals, or additions of natural or synthetic sequences can be performed. Adapters or linkers can be attached to DNA fragments to link them together.

[0034] Plant cells having gene products with reduced activity may be prepared by the following methods, for example, by expressing at least one suitable antisense RNA and sense RNA to achieve a co-repression effect, or by expressing at least one appropriately constructed ribozyme that specifically cleaves the transcript of the gene product.

[0035] For this purpose, DNA molecules can be used that contain all coding sequences of a gene product, including any possible adjacent sequences, and DNA molecules that contain only portions of the coding sequence that must be long enough to produce an antisense effect in a cell. Sequences that have a high degree of homology to the coding sequence of the gene product but are not completely identical can also be used.

[0036] When nucleic acid molecules are expressed in plants, the synthesized proteins may be localized in any desired compartment of the plant cell. However, to achieve localization in a particular compartment, for example, a DNA sequence and coding region can be linked to ensure localization at a specific location. 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).

[0037] Transgenic plant cells can be recombined throughout the entire plant using known techniques. Transgenic plants may be any desired plant species, i.e., monocots and dicots. In this way, transgenic plants can be obtained that have altered traits by overexpression, repression, or inhibition of homogeneous (=natural) genes or gene sequences, or by expression of heterogeneous (=foreign) genes or gene sequences.

[0038] When the active substance of the present invention is used in transgenic crops, in addition to the inhibitory effect on harmful plants that may be observed in other crops, there are often special effects in the corresponding transgenic crop, such as the improvement or expansion of the range of weeds that can be controlled, modification of application rates between applications, an excellent combination of drug resistance and herbicidal performance in the preferred transgenic crop, and effects on the growth and yield of the transgenic crop plant. The present invention therefore also provides the use of the compound as a herbicide for controlling harmful plants among transgenic crop plants.

[0039] Additionally, the compounds of the present invention can significantly regulate the growth of crop plants. These compounds are used for targeted control of plant components and to promote harvesting by inducing drought and growth arrest, for example, by engaging in plant metabolism in a regulatory manner. Furthermore, they are also suitable for regulating and inhibiting undesirable plant growth without disrupting the growth of crop plants. Inhibition of plant growth plays a key role in many monocotyledonous and dicotyledonous crops, as it can thereby reduce or completely prevent lodging.

[0040] The compounds of the present invention may be applied in conventional formulations in the form of hydrateable powders, emulsifiable concentrates, sprayable solutions, fine powders, or granules. The present invention therefore also provides herbicidal compositions comprising compounds of formula I or I'. Compounds of formula I or I' may be formulated in numerous ways depending on physical parameters widely used in biology and / or chemistry. Examples of preferred formulation options are: hydrateable powders (WP), water-soluble powders (SP), water-soluble concentrates, emulsifiable concentrates (EC), emulsions, e.g., oil-in-water and water-in-oil emulsions (EW), sprayable solutions, suspension concentrates (SC), oily dispersions (OD), oil or aqueous dispersions, oil-miscible solutions, fine powders (DP), capsule suspensions (CS), seed coating compositions, granules for broadcast and soil application, spray granules, coated granules and adsorbent granules, water-dispersible granules (WG), water-soluble granules (SG), ULV (Ultra-low volume) formulations, microcapsules, and waxes. These individual formulation types are known, and can be found in the following literature, for example, Winnacker-Kuchler, “Chemische Technologie” [Chemical Technology], Volume 7, C. Hauser Verlag Munich, 4 thedition, 1986;Wade van Valkenburg, “Pesticide Formulations”, Marcel Dekker, NY, 1973;K. Martens, “Spray Drying” Handbook, 3 rd This information is described in the 1979 edition, published by G. Goodwin Ltd., London.

[0041] The necessary formulation aids, such as inert materials, surfactants, solvents, and other additives, are also known, as can be seen in the following literature, e.g., Watkins, “Handbook of Insecticide Dust Diluents and Carriers”, 2 nd edition, Dorland Books, Caldwell NJ;H. v. Olphen, “An Introduction to Clay Colloid Chemistry”, 2 nd edition, J. Wiley & Sons, NY;C. Marsden, “Solvents Guide”, 2 nd edition, 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; [Chemical Technology], Volume 7, C. Hauser Verlag Munich, 4 thThis is described in the 1986 edition.

[0042] The hydrateable powder is uniformly dispersible in water and, in addition to the active substance, contains diluents or inert substances, ionic and nonionic surfactants (wetting agents, dispersants), such as polyethoxylated alkylphenols, polyethoxylated aliphatic alcohols, polyethoxylated aliphatic amines, aliphatic alcohol polyglycol ether sulfates, alkanesulfonates, alkylphenyl sulfonates, sodium lignosulfonates, sodium 2,2'-dinaphthylmethane-6,6'-disulfonate, sodium dibutylnaphthalene sulfonate, or sodium methyl oleoyl taurate. To prepare the hydrateable powder, the herbicidally active substance is finely ground, for example, in conventional equipment such as a hammer mill, fan mill, and air jet mill, and mixed simultaneously or sequentially with formulation aids.

[0043] Emulsifiable concentrates are prepared by dissolving the active substance in an organic solvent, such as butanol, cyclohexanone, dimethylformamide, xylene, or an aromatic compound with a relatively high boiling point, or a mixture of hydrocarbons or solvents, along with the addition of one or more ionic and / or nonionic surfactants (emulsifiers). Examples of emulsifiers that can be used are calcium alkylaryl sulfonates, such as calcium dodecylbenzenesulfonate, or nonionic emulsifiers, such as fatty acid polyglycol esters, alkylaryl polyglycol ethers, aliphatic alcohol polyglycol ethers, propylene oxide-ethylene oxide condensate products, alkyl polyethers, sorbitan esters, such as sorbitan fatty acid esters, or polyoxyethylene sorbitan esters, such as polyoxyethylene sorbitan fatty acid esters.

[0044] Fine powders are obtained by grinding the active substance with a finely divided solid material, such as talc, natural clay, such as kaolin, bentonite, and pyrophyllite, or diatomaceous earth. Aqueous or oily suspensions may be prepared by wet milling using a commercially common bead mill, for example, with or without the addition of the surfactants described above in the case of other formulation types.

[0045] Emulsions, such as oil-in-water emulsions (EWs), may be prepared using aqueous organic solvents by a stirrer, colloidal mill, and / or static mixer, and, if desired, surfactants such as those described above in the case of other formulation types may be added.

[0046] Granules may be prepared by the following methods, which involve spraying an active substance onto an adsorbent and granulating it together with an inert material, or concentrating an active substance on the surface of a support, such as soil and kaolinite, and granulating the inert material with a sticky binder, such as polyvinyl alcohol, sodium polyacrylate, or mineral oil. Suitable active substances may also be granulated in a conventional manner for the preparation of fertilizer granules. Fertilizer may be mixed in if desired. Water-dispersible granules are prepared by conventional methods, such as spray drying, fluidized bed granulation, disc granulation, or mixing using a high-speed mixer and extrusion without solid inert material.

[0047] For a method of preparing granules using a disc, fluidized bed, extruder, and spray, see, for example, “Spray-Drying Handbook” 3. rd edition, 1979, G. Goodwin Ltd., London; JE Browning, “Agglomeration”, Chemical and Engineering, 1967, pages 147 ff.; “Perry's Chemical Engineer's Handbook”, 5 thSee the process in edition, 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”, 5 th See edition, Blackwell Scientific Publications, Oxford, 1968, pages 101–103.

[0048] Agricultural chemical formulations generally contain 0.1 to 99%, particularly 0.1 to 95%, of the active substance of formula I or I' by weight. In hydrateable powders, the concentration of the active substance is, for example, about 10 to 99% by weight, and the remainder up to 100% by weight constitutes a typical formulation component. In emulsifiable concentrates, the concentration of the active substance may be about 1 to 90%, preferably 5 to 80%, by weight. Fine powder formulations typically contain 1 to 30%, preferably 5 to 20%, of the active substance by weight, while sprayable solutions contain about 0.05 to 80%, preferably 2 to 50%, of the active substance by weight. In the case of water-dispersible granules, the content of the active substance mainly depends on whether the active substance is liquid or solid, and on the auxiliary agents, fillers, etc., used during granulation. In the water-dispersible granules, the content of the active substance is, for example, 1 to 95% by weight, preferably 10 to 80% by weight.

[0049] In addition, the formulation of the active substance may also contain pH and viscosity modifiers, in addition to tackifiers, wetting agents, dispersants, emulsifiers, penetrating agents, preservatives, antifreezes, solvents, fillers, carriers, colorants, defoamers, and evaporation inhibitors, which are usually standard in all cases.

[0050] Based on these formulations, mixtures can also be produced in the form of premixes or tank mixes with other biocidally active substances, such as insecticides, acaricides, herbicides, and fungicides, as well as with toxicity mitigators, fertilizers, and / or plant growth regulators.

[0051] Suitable active substances that can be mixed with the active substance of the present invention in a mixed formulation or tank mix formulation are known substances described, for example, in the World Herbicide New Product Technology Handbook, China Agricultural Science and Farming Techniques Press, 2010.9 and in the literature referenced herein. For example, the herbicidally active substances listed below may be mixed with compounds of formula I or I' (compounds are named by their "generic name" or chemical name according to the International Organization for Standardization (ISO), and accompanied by a standard code number where appropriate): acetochlor, butachlor, alachlor, propisochlor, metrachlor, S-metrachlor, pretilachlor, propachlor, etachlor, napropamide, R-left (handed) Napropamide, Propanil, Mefenacet, Diphenamide, Diflufenican, Etaprochlor, Beflubutamide, Bromobutide, Dimethenamide, Dimethenamide-P, Etobenzanide, Flufenacet, Tenylchlor, Metazachlor, Isoxaben, Flamprop-M-methyl, Flamprop-M-propyl, Alidoclor, Petoxamide, Chloranocryl, Cybromide, Mefluidide, Monalide, Delacrol, Prinachlor, Terbuchlor, Xylacrol, Dimethachlor, Cisanilide, Trimexachlor, Clomeprop, Propyzamide, Pentanoclor, Carbetamide, Be Nzoylprop-ethyl, ciprazole, butenacrol, tebutam, benzipram, quinonamide, diclofluanide, naproanilide, dietatyl-ethyl, naptalam, flufenacet, benzadox, chlorthiamide, chlorophthalimide, isocarbamide, picolinafene, atrazine, simazine, promethrin, cyanatrin, simetryn, ametrin, propazine, dipropetrin, SSH-108, terbutrin, terbutyrazine, triaziflame, ciprazine, proglinadin, trietadine, prometon, simeton, adiprothrin, desmethrin, dimethametryn, procyazin, mesoprazineSebutyrazine, Sebumethone, Terbumetone, Metoprothrin, Cyanatrin, Ipazine, Chlorazine, Atlaton, Pendimethalin, Eglinadin, Cyanuric Acid, Indadiflame, Chlorsulfuron, Methosulfuron-methyl, Bensulfuron-methyl, Chlorimulon-ethyl, Trivenulon-methyl, Thifensulfuron-methyl, Pyrazosulfuron-ethyl, Mesosulfuron, Iodosulfuron-methylsodium, Forumsulfuron, Sinosulfuron, Triasulfuron, Sulfomethanemethyl, Nicosulfuron, Etamethosulfuron-methyl , amide sulfuron, ethoxysulfuron, cyclosulfamuron, limsulfuron, azimsulfuron, flazasulfuron, monosulfuron, monosulfuron ester, fulcarbazone sodium, flupyrsulfuron methyl, halosulfuron methyl, oxasulfuron, imazosulfuron, primisulfuron, propoxycarbazone, prosulfuron, sulfosulfuron, trifloxysulfuron, triflusulfuron methyl, tritosulfuron, metosulfuron methyl sodium, flucetosulfuron, HNPC-C9908, orthos Rufamuron, Propyrisulfuron, Metazosulfuron, Asifluorphen, Homesaphen, Lactofen, Fluoroglycofen, Oxyfluorphen, Chlornitrofen, Acronifen, Ethoxyphen-ethyl, Bifenox, Nitrofluorphen, Chlomethoxyfen, Fluorodifen, Fluoronitrofen, Fryloxifen, Nitrofen, TOPE, DMNP, PPG1013, AKH-7088, Halosaphen, Chlortoluron, Isoproturon, Linulon, Diuron, Dimlon, Fluomethuron, Benzthiazulon ( benzthiazuron), metabenzthiazuron, cumilon, ethidymulone, isouron, tebuthiuron, buturon, chlorbromulone, methyldimymulone, phenobenzuron, SK-85, metobromulone, methoxrone, afesin, monulone, sideuron, fenulon, fluothiurone, nevron, chloroxurone, norulone, isonorolone, 3-cyclooctyl-1, thiazflurone, tebuthiurone, diphenoxurone, paraflurone, methylaminetribnyl, carbthyrate, trimeturone,Dimeflon, Monisouron, Anistlon, Methylon, Chloretulon, Tetrafluron, Fenmedifam, Fenmedifam-ethyl, Desmedifam, Aslam, Terbucarb, Barban, Profam, Chlorprofam, Rowmate, Swep, Chlorbufam, Carboxazole, Chlorprocarb, Fenasulam, BCPC, CPPC, Carbasulam, Butyrate, Benchiocarb, Bemolate, Molinate, Trialate, Dimepiperate, Espu Locarb, pyributicarb, cycloate, avadex, EPTC, etiolate, olbencarb, pevlate, prosulfocarb, thiocarbasil, CDEC, dimexano, isopolinate, methibencarb, 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 propionate, 2,4-D butyric acid, MCPA propionic acid, MCPA propionate, M CPA butyric acid, 2,4,5-D,2,4,5-D propionic acid, 2,4,5-D butyric acid, MCPA amine salt, dicamba, erbon, chlorfenac, saison, TBA, chloramben, methoxy-TBA, diclofop-methyl, fluadifop-butyl, fluadifop-P-butyl, haloxyfop-methyl, haloxyfop-P, quizalofop-ethyl, quizalofop-P-ethyl, fenoxaprop-ethyl, phenoxaprop-P-ethyl, propaxifop, cyhalofop-butyl, meta Mihop, Clodinahop-propargyl, Fentiapropetyl, Chloroadifop-propynyl, Poppenate-methyl, Trifopsime, Isoxapyrhop, Paraquat, Diquat, Oryzalin, Etalfluralin, Isopropanin, Nitraline, Profluralin, Prodinamin, Benfluralin, Fluchloralin, Dinitramina, Dipropanin, Clomidine, Metalpropanin, Dinoprop, Glyphosate, Anirofos, Glufosinate Ammonium, Amiprophos-methylSulfosate, piperophos, biaphos sodium, benslid, butamiphos, phocarb, 2,4-DEP, H-9201, zytron, imazapyr, imazetapir, imazakine, imazamox, imazamox ammonium salt, imazapic, imazametabenz-methyl, fluroxypil, fluroxypil isooctyl ester, clopyralide, picloram, triclopil, dithiopil, haloxydine, 3,5,6-trichloro-2-pyridinol, thiazopil, fluridone, aminopyralide, diflufenzopil, triclopi Lu-butotyl, clio-dinate, cethoxydim, cretodim, cycloxidim, alloxidim, crehoxidim, butroxidim, tralcoxidim, tepraloxidim, butidazole, metrivudine, hexazinone, metamitron, ethiodin, ametridione, amivudine, bromoxynil, bromoxynil octanoate, ioxynil octanoate, ioxynil, diclobenil, diphenatril, pyraclonil, chloroxinil, iodobonyl, flumethoslam, florathlam, penoxulam, metoslam Chloranthramine-methyl, diclothram, piroxram, benfresate, bispyrivac-sodium, pyribenzoxime, pyrifthalide, pyriminovac-methyl, pyrithiovac-sodium, benzobisilone, mesotrione, sulcotrione, tembotrione, tefuryltrione, bicyclopyrone, ketodpiradox, isoxaflutol, cromazon, phenoxasulfone, methiozoline, fluazolate, pyraflufen-ethyl, pyrazolinate, diphenzocort, pyrazoxifen, benzophenate P, nipiraclofen, pyrasulfol, topramesone, pyroxasulfone, caffenstrol, flupoxam, aminotriazole, amicarbazone, azaphenidine, carfentrazone-ethyl, sulfentrazone, bencarbazone, benzfenizone, butafenacil, bromacil, isocyl, lenacil, terbacil, flupropacil, sinidone-ethyl, flumicrolac-pentyl, flumioxazine, S-23121, MK-129, flumazine, pentachlorophenol, dinoseb, dinoterb, dinoterb acetate, dinosam,DNOC, chloronitrofen, medinoterbacetate, dinophenate, oxaziargyl, oxadiazone, pentoxazone, fluphenacet, fluthiaset-methyl, phentrazamide, flufenpyr-ethyl, pyrazon, brompyrazone, metoflurazone, kusakira, dimidazon, oxapirazone, norflurazone, pyridafor, quinchlorac, kinmelac, bentazon, pyridate, oxazi Clomefon, Benazoline-ethyl, Chromazon, Symmethilin, ZJ0702, Pyribambenzupropyl, Indanophan, Sodium Chlorate, Darapon, Trichloroacetic Acid, Monochloroacetic Acid, Hexachloroacetone, Flupropanate, Sipercoat, Bromophenoxime, Epronaz, Metasol, Flulutamone, Benfresate, Etofmesate, Thiochlorim, Chlortal, Fluorochloridone, Tabron, Acrylic Acid Lorraine, Bentolanil, Tridiphan, Chlorfenpropmethyl, Thidiarizonaimin, Phenisophan, Busoxynone, Methoxyphenone, Saflufenacil, Clasifos, Chloropone, Allorac, Dietamcort, Etonipromide, Iprimidum, Ipfencarbazone, Thiencarbazone-methyl, Pyrimisulfan, Chlorflurazole, Tripropindan, Sulglycapine, Pros Rufarin, Cambenziclor, Aminocyclopyrachlor, Rodetanyl, Benoxacol, Fenchlorim, Flurazole, Fenchlorazole-ethyl, Croquintoset-mexyl, Oxavethrinyl, MG / 91, Siometrinyl, DKA-24, Mefenpyr-diethyl, Frillazole, Fluxofenim, Isoxadifen-ethyl, Dichlormid, Harauxifen-methyl, DOW848, 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, ET751, KIH-6127 and KIH-2023. ,

[0052] In one particular embodiment, the active substance (the additional herbicide in (iii) above) is selected from one or more of the following compounds: (1) VLCFA inhibitors: pretilachlor (CAS: 51218-49-6), butachlor (CAS: 23184-66-9), mefenacet (CAS: 73250-68-7), acetochlor (CAS: 34256-82-1), anilofos (CAS: 64249-01-0); (2) HPPD inhibitors: [ka] (CAS:2421252-30-2), tefuryltrione (CAS:473278-76-1), benzobicyclon (CAS:156963-66-5), bipirazone (CAS:1622908-18-2); (3) PPO inhibitors: Oxadiazone (CAS: 19666-30-9), pyraclonil (CAS: 158353-15-2), oxyfluorphen (CAS: 42874-03-3), oxaziargyl (CAS: 39807-15-3), pentoxazone (CAS: 110956-75-7), [ka] (CAS:2759011-88-4) [ka] ; (4) Synthetic hormones: Harauxifen-methyl (CAS: 943831-98-9), Florpyrauxifen-benzyl (CAS: 1390661-72-9), [ka] , Fluroxipir (CAS: 69377-81-7), [ka] (CAS:2445983-82-2); (5) PSII inhibitors: propanil (CAS: 709-98-8), bentazon (CAS: 25057-89-0), simetrin (CAS: 1014-70-6); (6) DOXP inhibitors: Chromazon (CAS: 81777-89-1) [ka] (CAS:2766607-82-1); (7) PDS inhibitors: Bixlozone (CAS: 81777-95-9) [ka] ; (8) FAT inhibitors: Symmethilin (CAS: 87818-31-3) [ka] ; (9) Other herbicides: Oxadiclomefone (CAS: 153197-14-9).

[0053] In another specific embodiment, the weight ratio of active ingredient (i) in the composition to the additional herbicide in (iii) is 1:100-100:1, 1:80-80:1, 1:50-50:1, 1:30-30:1, 1:20-20:1, 1:10-10:1, 1:5-1:1, or 1:1-5:1.

[0054] For use, commercially available formulations are diluted in a conventional manner if necessary, for example, with water in the case of hydrateable powders, emulsifiable concentrates, dispersions, and water-dispersible granules. For products in the form of fine powders, granules for soil application, or solutions for broadcasting and spraying, further dilution with inert materials is usually not required prior to use. The required application rate of compounds of formula I or I' varies with external conditions, such as temperature, humidity, and the properties of the herbicide used. It may have active material in a wide range, for example, 0.001 to 1.0 kg ai / ha or more, preferably 0.005 to 750 g ai / ha, and especially 0.005 to 250 g ai / ha.

[0055] Furthermore, another embodiment of the present application is a fungicidal composition comprising a disease-inhibiting and botanically acceptable amount of a compound of formula I or I'; preferably, in one particular embodiment, also comprising a formulation aid; and in another particular embodiment, further comprising another active ingredient.

[0056] Another embodiment of this application is the use of compounds of formula I or I' or the above-described fungicidal compositions in the prevention and control of plant pathogenic fungi for the purpose of protecting plants from parasitism by plant pathogenic microorganisms or treating plants that are attacked by plant pathogenic microorganisms. Use comprises applying compounds of formula I or I' or compositions of the compounds to soil, plants, parts of plants, leaves, and / or roots.

[0057] The compounds of this application may also be combined with other fungicides to form a fungicidal mixture. The compounds of this application are typically administered in combination with other fungicides to prevent and control widespread undesirable diseases. When administered in combination with other fungicides, the compounds claimed in this application may be formulated together with the other fungicide, tank-mixed with the other fungicide, or administered sequentially with the other fungicide. Other fungicides include 2-(thiocyanatomethylthio)-benzothiazole, 2-phenylphenol, 8-hydroxyquinoline sulfate, ametoctrazine, amisulbrom, antimycin, Ampelomyces quisqualis, azaconazole, azoxystrobin, Bacillus subtilis, Bacillus subtilis (subtilis) QST713 strain, venalaxyl, benomyl, benciavaricarb-isopropyl, benzylaminobenzene sulfonate (BABS), bicarbonate, biphenyl, bismelthiazole, vitertanol, bixafen, blastosidine-S, borax, Bordeaux mixture, boscalid, bromconazole, bupirimate, calcium polysulfide, captahole, captan, carbendazim, carboxyne, carpropamide, carvone, chlazafenone, chloroneb, chlorothalonil, chlozolinate, Coniothyrium minitans Minitans), copper hydroxide, copper octanoate, copper oxychloride, copper sulfate, copper sulfate (tribasic), copper oxide, cyazofamide, cyflufenamide, cymoxanil, cyproconazole, cyprodinil, dazomet, debacarb, diammoniumEthylene bis-(dithiocarbamate), diclofluanide, dichlorophene, diclocimet, diclomidine, dichlorane, diethofencarb, difenoconazole, diphenzocoat ion, diflumetrim, dimethomorph, dimoxystrobin, diniconazole, diniconazole-M, dinovtone, dinocup, diphenylamine, dithianone, dodemorph, dodemorph acetate, dozin, dozin free base, edifenphos, enestrobin, enestrobrin, epoxyconazole, etaboxam, ethoxyquin, etridiazole, famoxadone, phenamidon, phenalimol, fenbuconazole, fenflam, fenhexamide, phenoxanil, fenpiclonil, fenpropidine, fenpropimorph, fenpyrazamine, fentin, fentin acetate, fentin hydroxide (Hydroxide), Ferbam, Felimzon, Fluazinam, Fludioxonil, Flumorph, Fluopicolide, Fluopyram, Fluolimide, Fluoxastrobin, Fluquinconazole, Flusilazole, Flusulfamide, Fluthianil, Flutolanil, Flutriafor, Fluxapyroxad, Holpet, Formaldehyde, Fosetyl, Fosetyl-aluminum, Fuberidazole, Flalaxyl, Flamethopyr, Guazatin, Guazatin acetate, GY-81, Hexachlorobenzene, Hexaconazole, Himexazole, Imazalil, Imazalil sulfate, Imibenconazole, Iminoctadine, Iminoctadine triacetate, IminoctadineTris(albesylate), iodocarb, ipconazole, ipfenpyrazolone, iprobenphos, iprodione, iprovalicarb, isoprothiolane, isopyrazam, isothianil, kasugamycin, kasugamycin hydrochloride hydrate, kresoxim-methyl, laminarin, mancapper, mancozeb, mandipropamide, maneb, mephenoxam, mepanipyrim, mepronil, meptyl-dinocap, mercury chloride, mercury oxide Mercurous chloride, metalaxyl, metalaxyl-M, metam, metam-ammonium, metam-potassium, metam-sodium, metconazole, metasulfocarb, methyl iodide, methyl isothiocyanate, methylam, metminostrobin, metraphenone, mildiomycin, mycrobutanil, nabam, nitrotar-isopropyl, nualimol, octylinone, offrace, oleic acid (fatty acid), orysastrobin, oxy Sadixyl, oxycopper, oxypoconazole fumarate, oxycarboxyne, pefurazoate, penconazole, pencyclon, penflufen, pentachlorophenol, pentachlorophenyl laurate, penthiopyrad, phenylmercury acetate, phosphonic acid, phthalide, picoxystrobin, polyoxin B, polyoxin, polyoxolim, potassium bicarbonate, potassium hydroxyquinoline sulfate, probenazole, prochloraz, procymidone, propamocarb, propamocarb hydrochloride, propiconazole, propineb, proquinazide, prothioconazole, pyraclostrobin, pyrametostrobin, pyroxystrobin, pyrazofos, pyribencarb, pyributicarb, pyrifenox, pyrimethanil, pyriophenone, pyroquilon, quinoclamin, quinoxyfen, quintozen, Reynoutria saccharinensisCandida oleophila extract, sedaxane, silthiofam, simeconazole, sodium 2-phenylphenoxide, sodium bicarbonate, sodium pentachlorophenoxide, spiloxamine, sulfur, SYP-Z048, tar oil, tebuconazole, tebufloxin, technazene, tetraconazole, thiabendazole, tifluzamide, thiophanate-methyl, thyram, thiadinyl, tolclophos-methyl, tolfluanide, triadimephon, triadimenol, triazoxide, tricyclazole, tridemorph, trifloxystrobin, triflumizole, triforine, triticonazole, validamycin, valifenarate, valifenal, vinclozoline, zineb, ziram, zoxamide, Candida oleophila, Fusarium oxysporum Gliocladium species (oxysporum), Phlebiopsis gigantea, Streptomyces griseobiridis Trichoderma griseoviridis, (RS)-N-(3,5-dichlorophenyl)-2-(methoxymethyl)-succinimide, 1,2-dichloropropane, 1,3-dichloro-1,1,3,3-tetrafluoroacetone hydrate, 1-chloro-2,4-dinitronaphthalene, 1-chloro-2-nitropropane, 2-(2-heptadecyl-2-imidazolin-1-yl)ethanol, 2,3-dihydro-5-phenyl-1,4-dithiin-1,1,4,4-tetraoxide, 2-methoxyethylmercury acetate, 2-methoxyethylmercury chloride, 2-methoxyethylmercury silicate, 3-(4-chlorophenyl)-5-methylrhodanine, 4-(2-nitroprop-1-enyl)phenylthiocyanate (4-(2-nitroprop-1-enyl)phenyl thiocyanateme), ampropylphos, anilazine, adichiram, barium polysulfide, Bayer32394, benodanil, benquinox, bentalon, benzamacryl; benzamacryl-isobutyl, benzamorph, binapacril, bis(methylmercury) sulfate, bis(tributyltin) oxide, butthiobate, cadmium calcium copper zinc chromate sulfate, carbamorph, CECA, clobentiazon, chloraniformethane, chlorphenazole, chlorquinox, crimbazole, copper bis(3-phenyl salicylate), copper zinc chromate, cufraneb, cupric hydrazinium sulfate, cuprobum, cyclafamide, sipendazo Lu, cyproflam, decafentin, diclozol, diclozoline, diclobutrazol, dimethirimol, dinoctone, dinosulfone, dinoterbone, dipirithione, ditalimphos, dodicine, dorazoxolone, EBP, ESBP, etaconazole, etem, ethirim, phenaminosulf, phenapanil, fenitropan, fluotrimazole, flucarbanil, fluconazole, fluconazole-cis, flumecyclox, flofanate, gliodin, griseofulvin, halacrine, Hercules 3944, Hexylthiophos, ICIA0858, Isopamphos, Isobalezion, Mebenyl, Mecarbinzide, Metazoxolone, Metofloxam, Methylmercury dicyandiamide, Methosulfobax, Milneb, Mucochloroanhydride, Microzoline, N-3,5-Dichlorophenyl succinimide, N-3-Nitrophenylitaconimide, Natamycin, N-Ethyl mercurio-4-toluenesulfonanilide, Nickelbis(dimethyldithiocarbamate), OCH, Phenylmercury dimethyldithiocarbamate, Phenylmercury This may include nitrates, phosdiphen, prothiocarb; prothiocarb hydrochloride, pyracarboride, pyridinitrile, pyroxiclor, piroxiflu, quinacetol; quinacetol sulfate, quinazamide, quinconazole, ravenzazole, salicylanilide, SSF-109, sultropen, tecolam, thiadifluol, thiophen, thiochlorfenfim, thiophanate, thioquinox, thioxide, triamiphos, trialimol, triazbutyl, triclamide, urbacid, zarilamide, and any combination thereof.

[0058] Another embodiment of this application is a method for preventing and controlling harmful fungi, comprising treating a material, plant, soil or seed to be protected from fungi or fungal parasitism with a compound of formula I or I' or the above-described fungicidal composition.

[0059] The compounds have been found to possess significant mycogenic activity, particularly for agricultural use. Many of the compounds are especially effective for use with agricultural crops and horticultural plants.

[0060] The effectiveness of the above-mentioned compounds for fungi will be understood by those skilled in the art to establish the general utility of the compounds as mycicides.

[0061] The compound is active against a wide range of fungal pathogens. Exemplary pathogens include the following diseases: wheat leaf blight (Mycosphaerella graminicola), wheat red rust (Puccinia triticina), wheat yellow rust (Puccinia striiformis), apple black spot (Venturia inaequalis), grapevine powdery mildew (Uncinula necator), barley cloud blight (Rhynchosporium secalis), rice blast (Pyricularia oryzae), and soybean rust (Phakopsora pachilli). Pachyrhizi), wheat blight (Leptosphaeria nodorum), wheat powdery mildew (Blumeria graminis f. sp. tritici), barley powdery mildew (Blumeria graminis f. sp. hordei), cucurbitaceous plant powdery mildew (Erysiphe cichoracearum), cucurbitaceous plant anthracnose (Glomerella lagenarium), beet leaf spot (Cercospora beticola), tomato summer blight (Alternaria solanii) This may include, but is not limited to, causative agents of barley leaf spot (Cochliobolus sativus), as well as the specific active substance to be applied. The exact amount of active substance to be applied depends not only on the specific active substance being applied, but also on the desired specific action, the fungal species to be controlled and its growth stage, as well as the part of the plant or other product to be in contact with the compound. Therefore, not all compounds and formulations containing the compounds may be equally effective at similar concentrations, or may not be able to act on the same fungal species.

[0062] The compound is effective for disease inhibition and use in plants at botanically acceptable levels. The term "disease inhibition and botanically acceptable levels" refers to the amount of compound that kills or inhibits the plant disease to be controlled, but is not critically toxic to the plant. This amount is generally about 0.1 to about 1000 ppm (parts per million), preferably 1 to 500 ppm. The exact concentration of the compound required varies with the fungal disease to be controlled, the type of formulation used, the method of application, the specific plant species, and climatic conditions. A suitable application rate is typically about 0.10 to about 4 pounds / acre (about 0.01 to 0.45 grams / square meter, g / m²). 2 It is within the range of ).

[0063] Furthermore, another embodiment of the present application is an insecticidal composition comprising a biologically effective amount of a compound of formula I or I'; preferably, in one particular embodiment, also comprising a formulation aid; and in another particular embodiment, further comprising another active ingredient.

[0064] Another embodiment of this application is the use of compounds of formula I or I' or the above-mentioned insecticidal compositions in the prevention and control of pests.

[0065] Another embodiment of this application is a method for preventing and controlling pests, comprising exposing the pests or their environment to a biologically effective amount of a compound of formula I or I' or the above-mentioned insecticidal composition.

[0066] In one particular embodiment, a biologically effective amount of the compound or composition defined above is used to treat pests, their food sources, their habitat or mating sites; or cultivated plants, plant propagation materials (e.g., seeds), soil, plots, materials or environments on or where pests may grow; or materials, cultivated plants, plant propagation materials (e.g., seeds), soil, surfaces or spaces that should be protected from attack or parasitism by pests.

[0067] The term "pest control" refers to inhibiting the occurrence of pests (including death, reduced feeding, and / or interference with mating), and related expressions may be defined similarly.

[0068] Additionally, the compounds described herein may be combined with other pesticides, including insecticides, nematodetrists, miticides, arthropodicides, fungicides, or combinations thereof, which are compatible with the compounds of this application in a medium selected for application and are not antagonistic to the activity of the compounds of this application, to form a pesticide mixture. The compounds of this application may be applied in combination with one or more other pesticides to control a broader variety of undesirable pests. When used in combination with other pesticides, the compounds claimed in this application may be formulated with the other pesticides, tank-mixed with the other pesticides, or applied sequentially with the other pesticides. Typical insecticides include 1,2-dichloropropane, abamectin, acephate, acetamiprid, acetylone, acetoprole, acrinatrin, acrylonitrile, alanicarb, aldicarb, aldoxycarb, aldrin, allethrin, allosamidin, alixicarb, alpha-cypermethrin, alpha-ecdysone, alpha-endosulfan, amidithione, aminocarb, amiton, amiton oxalate, amitraz, anabasin, atidathion, azadirachtin, azamethiphos, azinphos-ethyl, azinphos-methyl, azothoate, barium hexafluorosilicate, bartholin, benziocarb, benfuracarb, bensultap, beta-cyfluthrin, beta-cypermethrin, bifenthrin, bioallethrin, and bi Oetanomethrin, Biopermethrin, Bistrifluron, Borax, Boric acid, Bromfenbinphos, Bromocyclene, Bromo-DDT, Bromophos, Bromophos-ethyl, Bufencarb, Buprofezin, Butacarb, Butathiophos, Butocarboxime, Butonate, Butoxycarboxime, Kazusaphos, Calcium arsenate, Calcium polysulfide, Campechlor, Carbanolate, Carbaryl, Carbofuran, Carbon disulfide, Carbon tetrachloride, Carbophenothione, Carbosulfan, Cartap, Cartap hydrochloride, Chlorantraniliprole, Chlorbicyclene, Chlordan, Chlordecone, Chlordimeform, Chlordimeform hydrochloride, Chlorethoxyphos, Chlorfenapyr, Chlorfenbinphos, Chlorfluazuron, Chlormephos,Chloroform, chloropicrin, chlorphoxime, chlorprazofos, chlorpyrifos, chlorpyrifos-methyl, chlorthiofos, chromafenozide, synerin I, synerin II, synerin, cismethrin, chloetocarb, closantel, clothianidin, copper acetoarsenite, copper arsenate, copper naphthenate, copper oleate, coumaphos, cumitoate, crotamiton, clotoxyfos, clufomate, criolite, cyanophenphos, cyanophos, cyantrate, cyantraniliprole, ciclethrin, cycloprothrin, cyfluthrin, cyhalothrin, Cypermethrin, Cyphenothrin, Cyromazine, Cythioate, DDT, Decarbofuran, Deltamethrin, Demefion, Demefion-O, Demefion-S, Demeton, Demeton-Methyl, Demeton-O, Demeton-O-Methyl, Demeton-S, Demeton-S-Methyl, Demeton-S-Methylsulfone, Diafenthiurone, Dialiphos, Diatomaceous Earth, Diazinon, Dicapton, Diclofenthion, Dichlorvos, Diclesyl, Diclotophos, Dicyclanil, Dierdrin, Diflubenzuron, Dirol, Dimefluthrin, Dimefox, Dimeta Dimethoate, Dimethrin, Dimethylvinphos, Dimethilane, Dynex, Dynex-Dicrexin, Dinoprop, Dinosum, Dinotefuran, Diophenolane, Dioxabenzophos, Dioxacarb, Dioxathion, Disulfon, Diticlophos, d-Limonene, DNOC, DNOC-Ammonium, DNOC-Potassium, DNOC-Sodium, Doramectin, Ecdysterone, Emamectin, Emamectin Benzoate, EMPC, Empenthrin, Endosulfan, Endothion, Endrin, EPN, Epophenonane, Eprinomectin Esdepallethrine, esfenvalerate, etaphos, ethiofencarb, ethione, ethiprole, etoate-methyl, etoprophos, ethyl formate, ethyl-DDD, ethylenedibromide, ethylenedichloride, ethyleneoxide, etofenprox, etrimphos, EXD, famfur, phenamiphos, phenazaflor, fenchlorphos, phenetacarb, fenfluthrin, fenitrothion, phenobucarb, phenoxacrim, phenoxycarb, fenpyritrin, fenpropathrin,Fensulfothione, fenthion, fenthion-ethyl, fenvalerate, fipronil, flonicamide, flubendiamide, flucoflon, flucycloxlon, flucitrinate, fluphenelim, flufenoxlon, flufenprox, fluvalinate, honofos, formmethanate, formmethanate hydrochloride, formothion, formparanate, formparanate hydrochloride, fosmethilan, fospilate, fosthiethane, flatiocarb, fretrin, gamma-cyhalotrin, gamma-HCH, halfenprox, halophenozide, H CH, HEOD, heptachlor, heptenofos, heterophos, hexaflumurone, HHDN, hydramethylnon, hydrogen cyanide, hydroprene, hikincarb, imidacloprid, imiprothrin, indoxacarb, iodomethane, IPSP, isazofos, isobenzan, isocarbos, isodrine, isofenphos, isofenphos-methyl, isoprocarb, isoprothiolane, isothioate, isoxathion, ivermectin, jasmolin I, jasmolin II, iodophenphos, juvenile hormone I, juvenile hormone II, juvenile hormone III Kereban, Quinoprene, Lambda-cyhalothrin, Lead Arsenate, Lepimectin, Leptophos, Lindan, Lilimphos, Lufenulon, Litidathion, Malathion, Malonoben, Magidox, Mecarbam, Mecarbhon, Menazone, Mephosphoran, Mercurous Chloride, Mesulfenphos, Metaflumizone, Methacryphos, Methamidophos, Methidathion, Methiocarb, Metoclotophos, Methomyl, Methoprene, Methoxychloride, Methoxyphenozide, Methyl Bromide, Methyl Isothiocyanate, Methylchloroform, Methylene Chloride, Metofluthrin, Metocarb, Metox Sadiazone, Mevinfos, Mexacarbate, Milbemectin, Milbemycin oxime, Mipafox, Myrex, Molosultap, Monoclotophos, Monomehypo, Monosultap, Morphothion, Moxidectin, Naphthalophos, Nared, Naphthalene, Nicotine, Nifiuridide, Nitenpyram, Nichiazine, Nitrilacarb, Novalon, Noviflumuron, Omethoate, Oxamyl, Oxidemeton-methyl, Oxideprophos,Oxydisulfone, para-dichlorobenzene, parathion, parathion-methyl, penfiuron, pentachlorophenol, permethrin, fencapton, phenothrin, fenthoate, phorate, phosalon, phospholan, phosmet, phosnichlor, phosphamidone, phosphine, phoxim, phoxim-methyl, pyrimetaphos, pyrimicarb, pyrimiphos-ethyl, pyrimiphos-methyl, potassium arsenite, potassium thiocyanate, pp'-DDT, prallethrin, precosen I, precosen II, precosen III, pri Midophos, Profenofos, Profluralin, Promacil, Promecarb, Propaphos, Propetamphos, Propoxul, Protidathion, Prothiofos, Protoate, Protrefenbute, Piraclofos, Pyrafiuprole, Pyrazofos, Pyrethmetrin, Pyrethrin I, Pyrethrin II, Pyrethrin, Pyridaben, Pyridaryl, Pyridafenthion, Pyrifiuquinazon, Pyrimidifen, Pyrimitate, Pyriprole, Pyriproxyfen, Quassia, Quinalfos, Quinalfo S-methyl, quinothion, rahoxanide, resmethrin, rotenone, lyania, sabadilla, shlardan, selamectin, silafluofen, silica gel, sodium arsenite, sodium fluoride, sodium hexafluorosilicate, sodium thiocyanate, sofamide, spinetoram, spinosad, spiromesifen, spirotetramato, sulcoflon, sulcoflon-sodium, sulfuramide, sulfotep, sulfoxaflor, sulfuryl fluoride, sulfurophos, tau-fluvalinate, tadimucarb, TDE, tebufenozide, tebufen Pyrado, Tebupyrimfos, Teflubenzuron, Tefluthrin, Temefos, TEPP, Terarethrin, Terbufos, Tetrachloroethane, Tetrachlorvinfos, Tetramethrin, Tetramethylfluthrin, Theta-cypermethrin, Thiacloprid, Thiamethoxam, Cyclophos, Thiocarboxime, Thiocyclam, Thiocyclam oxalate, Thiodicarb, Thiofanox, Thiometon, Thiosultap, Thiosultap-disodium, Thiosultap-monosodium, Turingiencin, Tolfenpyrad, Tralomethrin, Transfluthrin,This includes, but is not limited to, transpermethrin, triaten, triazamate, triazophos, trichlorfon, trichlormetaphos-3, trichloronate, tripenophos, triflumulone, trimetacarb, triprene, bamidothion, vaniliprole, XMC, xylicarb, zeta-cypermethrin, zolaprophos, and any combination thereof.

[0069] The term “biologically effective amount” refers to an amount of a biologically active compound (e.g., compounds of formulas I and I') that, when applied (i.e., in contact with) a pest to be controlled, or its environment, or a plant, seeds from which the plant has grown, or the location of the plant (e.g., a growth medium), produces a desired biological effect, thereby protecting the plant from damage caused by the pest or achieving another desired effect (e.g., increasing the plant’s activity). The compounds of the present invention may also be applied preventively when the appearance of pests or parasites is anticipated.

[0070] The content of the compound as an active ingredient may vary as required, and the compound as an active ingredient may be used in a proportion appropriately selected within the range of 0.01 to 90 parts by weight per 100 parts by weight of the agricultural and horticultural agent of the present invention. For example, in fine powder, granules, emulsion, or hydrateable powder, a suitable content of the compound as an active ingredient is 0.01 to 50 parts by weight (0.01 to 50 wt%) of the total weight of the agricultural and horticultural insecticide.

[0071] The applicable amount of the horticultural insecticide of the present invention varies depending on various factors, such as purpose, pest to be controlled, plant growth stage, pest emergence tendency, weather, environmental conditions, form of preparation, application method, application site, and number of applications. It may be appropriately selected within the range of 0.001 g to 10 kg, preferably 0.01 g to 1 kg, per 10 acres (in terms of the compound as the active ingredient), depending on the purpose. [Brief explanation of the drawing]

[0072] [Figure 1]Figure 1 shows a chart of the single crystal X-ray structure analysis of Compound 117' of the present invention.

Mode for Carrying Out the Invention

[0073] Detailed Embodiments of the Invention The following examples are used to illustrate examples of the present invention and should not be construed as limiting the present invention in any way. The scope of the rights claimed by the present invention is described in the claims.

[0074] Considering the economy and diversity of the compounds, several compounds were preferably synthesized. Among the many synthesized compounds, the selected ones are listed in Table 1 below. The structures of the specific compounds and the corresponding compound information are as shown in Tables 1 and 2. The compounds in Table 1 are only for better illustrating examples of the present invention and do not limit the present invention. Those skilled in the art should not understand that the scope of the above subject matter of the present invention is limited to the following compounds.

[0075]

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

[0076] Table 2-1 Table 2-2 Table 2-3 Table 2-4 Table 2-5 Table 2-6 Table 2-7 Table 2-8 Table 2-9 Table 2-10 Table 2-11 Table 2-12 Table 2-13 Table 2-14 Table 2-15 Table 2-16 Table 2-17 Table 2-18 Table 2-19 Table 2-20 Table 2-21 Table 2-22

[0077] Table A has the same structure as Table 1 above, except that General Formula I has a chiral center, and General Formula I' [ka] It has been replaced, and in Table A, the items in the column with the heading "Number" are listed sequentially as 1'-562'. For example, 1' is compound 1 in Table 1, which has an S configuration at both the 3rd and 4th positions. [ka] Corresponding to; 30' is compound 30 in Table 1, which has an S configuration at both the 3rd and 4th positions. [ka] Corresponding to; 340' is compound 340 in Table 1, which has S and R configurations at positions 3 and 4, respectively. [ka] It corresponds to.

[0078] Examples of several methods for preparing the compounds of the present invention are shown in detail in the following schemes and examples. The raw materials can be purchased on the market or prepared by methods known in the literature or described in the detailed description. Those skilled in the art should understand that other synthetic routes may also be used to synthesize the compounds of the present invention. Specific raw materials and conditions in the synthetic routes are shown below, but they can be readily substituted with other similar raw materials and conditions. All various isomers of the compounds resulting from these modifications or variations of the preparation methods of the present invention are within the scope of the present invention. In addition, the preparation methods described below can be further modified in accordance with the disclosure of the present invention using conventional chemical methods well known to those skilled in the art, such as protection for appropriate groups during the reaction.

[0079] The examples of the methods provided below are used to enhance a further understanding of the preparation methods of the present invention. The specific substances, varieties, and conditions used are determined to further illustrate the present invention, rather than to limit the reasonable scope of the present invention. The reagents used in the synthesis of the compounds shown below are commercially available or can be readily prepared by those skilled in the art.

[0080] Examples of representative compounds are given below. The synthesis methods for other compounds are similar and are not described in detail herein.

[0081] 1. Synthesis of Compound 1 Py-BOP (6.80 g, 13.1 mmol), compound 1-1 (1.72 g, 13.1 mmol), and triethylamine (2.41 g, 17 mmol) were added to a DCM solution (100 mL) of compound 1-2 (2.50 g, 8.71 mmol) and stirred at room temperature. Water (100 mL x 3) was added for extraction. The organic phase was dried over anhydrous sodium sulfate, silica gel powder was added, and the mixture was concentrated by reduced pressure. The solvent was completely removed by rotary evaporation, followed by normal-phase purification (mobile phase was petroleum ether:ethyl acetate = 1:1) to obtain compound 1 (2 g, yellow solid). [ka]

[0082] 2. Synthesis of compound 17' (1) Compound 17-1 (5 g) was added to a flask, THF was added, and the mixture was stirred to a homogeneous degree. At 0°C, 3 equivalents of potassium tert-butoxide were added to the system all at once, and then 2 equivalents of methyl iodide were slowly added dropwise using a pressure-equalized dropping funnel, after which the reaction was allowed to proceed at room temperature. After the reaction, the system was treated by adjusting the pH to acidity, extraction, filtration, and drying to obtain 3 g of compound 17-2. [ka]

[0083] (2) Compound 17-2 (300 mg, 1 equivalent), pyrazole compound 1-1 (1.2 equivalents), EDCI (1.5 equivalents), HOBT (1.5 equivalents), triethylamine (3 equivalents), and dichloromethane (10 mL) were added to a 50 mL one-necked flask and reacted at room temperature for 4 hours. Compound 17' (60 mg, 92% yield) was obtained by column chromatography. [ka]

[0084] 3. Synthesis of Compound 30 (1) Compound 30-1 was prepared with reference to compound 17-2. Compound 30-1 (2 g) was dissolved in 20 mL of DCM, and boron tribromide (5 equivalents) was added in an ice bath and the mixture was reacted for 30 minutes. After the process control was completed, methanol was added to the reaction solution to quench it, and the reaction solution was spin-dried to obtain the product, compound 30-2 (1.9 g, white solid). [ka]

[0085] (2) 100 mg of compound 30-2 was dissolved in 5 mL of acetonitrile, potassium carbonate (2 equivalents) was added, and 30-3 (1.2 equivalents) was added, and the reaction was carried out overnight at 30°C. After the in-process control was completed, silica gel was immediately added to the reaction solution, stirred, and separated by silica gel column chromatography to obtain compound 30-4 (90 mg, white solid). [ka]

[0086] (3) 90 mg of compound 30-4 was dissolved in 3 mL of dioxane, 2 mL of water was added, and sodium hydroxide (1.5 equivalents) was added, and the mixture was reacted for 30 minutes. After in-process control was completed, the reaction solution was concentrated by vacuum concentration to remove the dioxane, the pH was adjusted to acidity with HCl, and the mixture was extracted twice with DCM. The organic phase was dried and spin-dried to obtain compound 30-5 (70 mg, pale yellow solid). [ka]

[0087] (4) 70 mg of compound 30-5 was dissolved in 3 mL of DCM, triethylamine (1.5 equivalents) was added, compound 1-1 (1.2 equivalents) was added, and Py-BOP (1.5 equivalents) was added, and the mixture was reacted for 30 minutes. After in-process control was completed, silica gel was added to the reaction solution, stirred, and spin-dried. The mixture was then separated and purified through a silica gel column to obtain compound 30 (60 mg, white solid). [ka]

[0088] 4. Synthesis of Compound 53 (1) 50 mL of dichloromethane, compound 30-1 (300 mg, 1 equivalent), pyrazole compound 1-1 (240 mg, 1.5 equivalents), triethylamine (240 mg, 2 equivalents), and Py-BOP (915 mg, 1.5 equivalents) were added to a 100 mL three-necked flask and reacted at room temperature for 4 hours. After the reaction was complete, the reaction solution was extracted with water and dichloromethane. The organic phase was dried on anhydrous sodium sulfate to remove water, concentrated under reduced pressure to remove the solvent, and purified by silica gel column chromatography to obtain compound 53-1 (200 mg, 95% purity), a white solid product. [ka]

[0089] (2) 30 mL of dichloromethane and compound 53-1 (200 mg, 1 equivalent) were added to a 100 mL three-necked flask. Boron tribromide (414 mg, 3 equivalents) was added to the system in an ice bath and allowed to rise naturally to room temperature for 4 hours to allow the reaction to continue. After the reaction was complete, the reaction mixture was quenched with methanol, and water and dichloromethane were used for extraction. The organic phase was dried over anhydrous sodium sulfate to remove water, concentrated under reduced pressure to remove the solvent, and spin-dried to obtain solid compound 53-2 (176 mg, 95% purity, crude product) for use in the next step. [ka]

[0090] (3) 30 mL of DMF, compound 53-2 (100 mg, 1 equivalent), compound 53-3 (45 mg, 1.2 equivalents), and anhydrous potassium carbonate (120 mg, 3 equivalents) were added to a 100 mL three-necked flask and reacted at 50°C for 4 hours. After the reaction was complete, the reaction solution was extracted with water and ethyl acetate. The organic phase was washed twice with saturated brine, dried on anhydrous sodium sulfate to remove water, concentrated under reduced pressure to remove the solvent, and purified by silica gel column chromatography to obtain compound 53 (30 mg, 89% purity), a white solid product. [ka]

[0091] 5. Synthesis of Compound 97 15 mL of DCM, compound 1-2 (0.100 g, 1.0 equivalent), compound 97-1 (0.836 g, 1.5 equivalents), TEA (0.710 g, 2.0 equivalents), and Py-BOP (0.270 g, 1.5 equivalents) were added to a 50 mL round-bottom flask and reacted at room temperature for 2 hours. After the reaction was complete, the reaction solution was extracted with water and ethyl acetate, dried on anhydrous sodium sulfate, concentrated under reduced pressure to remove the solvent, and purified by silica gel column chromatography to obtain compound 97 (30 mg, 92% purity, 19% yield), a yellow oily substance. [ka]

[0092] 6. Synthesis of Compound 117' (1) 100 g of compound 117-1 was dissolved in 200 mL of glacial acetic acid, nitromethane (3.0 equivalents) and ammonium acetate (0.5 equivalents) were added, the mixture was purged with nitrogen gas, and the reaction was carried out at 100-105°C for 2-5 hours. Completion of the reaction was detected by HPLC. The reaction system was cooled to 20-25°C, 200 mL of purified water was added, and the mixture was filtered. The filtered cake was immersed and washed twice with 200 mL x 2 of isopropanol, dried, and 90 g of yellow solid compound 117-2 was obtained in 68% yield. [ka]

[0093] (2) A total of 100 g of compound 117-2 was dissolved in 500 mL of toluene, 5% w / w of catalyst (CAS number: 862910-64-3) and diethyl malonate (1.25 equivalents) were added, the mixture was purged with nitrogen gas, and the reaction was carried out at 55-60°C for 3-5 hours. Completion of the reaction was detected by HPLC. The reaction system was cooled to 20-25°C. The organic phase was sequentially washed once each with 200 mL of purified water and 200 mL of 15% saline solution. The organic phase was concentrated by vacuum concentration until no fraction was generated, 300 mL of n-heptane was added, and the mixture was slurryed at 20-25°C for 1 hour and filtered. The filtered cake was dried to obtain 170 g of pale yellow solid compound 117-3 in (S):(R) = 97:3 and 80% yield. [ka]

[0094] (3) 100 g of compound 117-3 was dissolved in 800 mL of MeOH, NiCl2·6H2O (0.5 equivalents) was added, and the mixture was kept at 0-20°C. NaBH4 (3.0 equivalents) was added all at once, and the mixture was allowed to react at room temperature for 3 hours. Completion of the reaction was detected by in-step control of the HPLC process. A methanol reaction solution of compound 117-4 was obtained, and the next reaction was carried out directly without any post-treatment. [ka]

[0095] (4) 200 mL of purified water and NaOH (3.0 equivalents) were added to the methanol reaction solution of compound 117-4 obtained in the preceding step, and the mixture was reacted at 20-25°C for 24 hours. Completion of the reaction was detected by in-step control of HPLC. The reaction solution was adjusted to pH=2 using 4M HCl, extracted with 300 mL of DCM, and concentrated to obtain 70 g of crude compound 117-5 for direct use in the next step. [ka]

[0096] (5) 70 g of crude compound 117-5 was dissolved in 560 mL of THF, and tBuOK (3.0 equivalents) and dimethyl sulfate (1.5 equivalents) were added at 0°C and the mixture was stirred at room temperature for 2 hours. Completion of the reaction was detected by in-step control of HPLC. 280 mL of purified water was added to the reaction solution and it was concentrated. The concentrate was adjusted to pH=2 using 4 M HCl and filtered. The filtered cake was recrystallized using 350 mL of ethyl acetate and dried to obtain 45 g of white solid compound 117-6 in 65% yield over three steps (from compound 117-3 to compound 117-6) with a (3R,4S):(3S,4R)=97:3. [ka]

[0097] (6) A total of 100 g of compound 117-6 was dissolved in 300 mL of DCE, 1 mL of DMF was added, and oxalyl chloride (1.1 equivalents) was added dropwise at 40-42°C. Completion of the reaction was detected by in-process control of HPLC. The DCE was concentrated by vacuum concentration, and 300 mL of DCM was added to obtain a solution of compound 117-5 chloride. The above solution was added dropwise at 40-42°C to a solution of compound 1-1 (1.0 equivalent) in DCM. After completion of the addition, the system was allowed to react for 0.5 hours. Completion of the reaction was detected by in-process control of HPLC. The temperature was cooled to 20-25°C. The DCM organic phase was sequentially washed three times with 200 mL x 3 of purified water, once with 200 mL of saturated sodium carbonate solution, and twice with 200 mL x 2 of purified water. The DCM organic phase was concentrated by vacuum concentration, and 120 mL of anhydrous ethanol was added for recrystallization. The solution was filtered. The filtered cake was washed three times with anhydrous ethanol at 0-5°C and dried to obtain compound 117', a 120 g pale yellow solid product with a (3S,4S):(3R,4R)>99:1 ratio and an 83% yield. Its absolute configuration was determined by single-crystal X-ray diffraction (see Figure 1). [ka]

[0098] 7. Synthesis of Compound 122 (1) 2.2 g of raw material compound 122-1 was dissolved in tetrahydrofuran, and 2 equivalents of potassium tert-butoxide were added in an ice bath, followed by the addition of 1.2 equivalents of methyl iodide dropwise. The reaction was allowed to proceed at room temperature for 1 hour. After the process control was completed, water was added to quench the reaction solution. The aqueous phase was adjusted to an acidic pH, the solution was extracted with EA, and dried to obtain 2 g of white solid compound 122-2. [ka]

[0099] (2) 150 mg of compound 122-2 was dissolved in dichloromethane, 1.1 equivalents of pyrazole compound 1-1 were added, 1.5 equivalents of EDCI were added, and 1.5 equivalents of HATU were added, and the mixture was reacted at room temperature for 1 hour. After in-process control was completed, water was added to the reaction solution to quench it, washed with dilute hydrochloric acid, extracted with EA, dried, and obtained 134 mg of white solid compound 122 by normal-phase column chromatography. [ka]

[0100] 8. Synthesis of Compound 155 (1) Compound 155-1 (15 g, 0.0508 mol, 1 equivalent) was dissolved in DMF (150 mL). At room temperature, benzyl bromide (8.69 g, 0.0508 mol, 1 equivalent) was added to the reaction solution and the reaction was carried out overnight at normal temperature. When liquid chromatography detected that the raw materials had been completely consumed, the aqueous phase was extracted with water and ethyl acetate until no product remained in it. The ethyl acetate phase was dried and concentrated to obtain 19 g of compound 155-2 (97% yield). [ka]

[0101] (2) Compound 155-2 (19 g, 0.049 mol, 1 equivalent) was dissolved in DCE (150 mL), catalytic amounts of DMF and POCl3 (22.65 g, 0.147 mol, 3 equivalents) were added, and the reaction was carried out overnight at 60°C. When liquid chromatography detected that the raw materials had been completely consumed, water was added to the reaction solution to quench it (temperature controlled), NaHCO3 solution was added to adjust the pH to 7, and the solution was separated. The organic phase was dried and concentrated to obtain the crude product, which was then purified to obtain compound 155-3 (5.2 g, 25% yield). [ka]

[0102] (3) Compound 155-3 (5.2 g, 0.012 mol, 1 equivalent) was dissolved in MeCN (50 mL), 20% (wt:wt) molecular sieve was added, K2CO3 (4.0 equivalents) and diethyl malonate (1.5 equivalents) were added, and the reaction was carried out overnight at 60°C. When liquid chromatography detected that the raw materials had been completely consumed, K2CO3 was filtered off. The organic phase was concentrated, stirred, and purified through a silica gel column to obtain the product, compound 155-4 (5 g, 73% yield). [ka]

[0103] (4) Compound 155-4 was dissolved in MeOH, 0.05 equivalents of wet Pd / C (10%) were added, and the mixture was reacted at 50°C for 24 hours under a double-layer hydrogen balloon (approximately 15 psi). When completion of the reaction was detected by liquid chromatography, the wet Pd / C was filtered off. The mother liquor was concentrated, stirred, and purified to obtain the product, compound 155-5. [ka]

[0104] (5) Compound 155-5 (1 equivalent) and NaOH (3.5 equivalents) were dissolved in a mixed solvent (dioxane:H2O=3:1) and reacted at normal temperature for 30 minutes. When completion of hydrolysis was detected, the reaction solution was concentrated, water was added, and it was extracted three times with DCM. The aqueous phase was adjusted to pH=4 and extracted with DCM. The organic phase was dried and concentrated to obtain the product, white solid compound 155-6. [ka]

[0105] (6) Compound 155-6 (150 mg, 0.0004 mol, 1 equivalent), compound 1-1 (1 equivalent), and triethylamine (2 equivalents) were dissolved in dichloromethane, and HATU (2 equivalents) was added with stirring. The mixture was reacted at normal temperature for 60 minutes. When completion of the reaction was detected, the reaction solution was concentrated, stirred, and purified to obtain the product, white solid compound 155-7 (30 mg, 15% yield). [ka]

[0106] (7) Compound 155-7 (100 mg, 0.00021 mol, 1 equivalent) was dissolved in MeOH, 0.05 equivalents of wet Pd / C (10%) were added, and the mixture was reacted at 50°C for 24 hours under a double-layer hydrogen balloon (approximately 15 psi). When completion of the reaction was detected by liquid chromatography, the wet Pd / C was filtered off. The mother liquor was concentrated, stirred, and purified to obtain compound 155 (80 mg, 86% yield). [ka]

[0107] 9. Synthesis of Compound 160' (1) 20 mL of EtOH, 2 mL of H2O, compound 160-1 (0.500 g, 1.0 equivalent), iron powder (0.880 g, 5.5 equivalents), and ammonium chloride (0.460 g, 3.0 equivalents) were added to a 50 mL round-bottom flask and reacted overnight at 50°C. After the reaction was complete, the reaction solution was filtered through diatomaceous earth and extracted with water and dichloromethane. The organic phase was washed twice with saturated brine and concentrated under reduced pressure to remove the solvent and obtain compound 160-2 (400 mg, 60% purity, 80% yield), a yellow oily substance. [ka]

[0108] (2) 20 mL of DCM, compound 160-2 (0.400 g, 1.0 equivalent), and triethylamine (0.900 g, 3.0 equivalents) were added to a 50 mL round-bottom flask, and Boc-acid anhydride (0.720 g, 1.2 equivalents) was added with stirring, and the reaction was allowed to proceed overnight at room temperature. Once the reaction was complete, the reaction solution was extracted with water and dichloromethane. The organic phase was washed twice with saturated brine, and the solution was concentrated under reduced pressure to remove the solvent and obtain compound 160-3 (240 mg, 80% purity, 70% yield), a yellow oily substance. [ka]

[0109] (3) 20 mL of DMF, compound 160-3 (0.240 g, 1.0 equivalent), and N-chlorosuccinimide (0.105 g, 0.8 equivalents) were added to a 50 mL round-bottom flask and reacted overnight at 30°C. After the reaction was complete, the reaction solution was extracted with water and dichloromethane. The organic phase was washed twice with saturated brine, and the solution was concentrated under reduced pressure to remove the solvent and obtain compound 160-4 (330 mg, 80% purity, 70% yield), a yellow oily substance. [ka]

[0110] (4) 20 mL of EA / HCl and compound 160-4 (0.330 g, 1.0 equivalent) were added to a 50 mL round-bottom flask and the mixture was stirred and allowed to react overnight at room temperature. Once the reaction was complete, the product was precipitated, then filtered, and concentrated under reduced pressure to remove the solvent and obtain a white solid compound 160-5 (130 mg, 80% purity, 50% yield). [ka]

[0111] (5) 15 mL of DCM, compound 160-5 (0.130 g, 1.0 equivalent), compound 160-6 (0.145 g, 0.7 equivalent), triethylamine (0.220 g, 3.0 equivalent), and 1-hydroxybenzotriazole (0.150 g, 1.5 equivalent) were added to a 50 mL round-bottom flask, and 1-ethyl-(3-dimethylaminopropyl)carbodiimide hydrochloride (EDCI) (0.210 g, 1.5 equivalent) was added with stirring, and the mixture was reacted at room temperature for 1 hour. After the reaction was complete, the reaction solution was extracted with water and dichloromethane. The organic phase was washed twice with saturated brine, concentrated under reduced pressure to remove the solvent, and purified by silica gel column chromatography to obtain a white solid compound 160' (80 mg, 96% purity, 20% yield). [ka]

[0112] 10. Synthesis of Compound 221 (1) 750 mg of compound 30-2 was dissolved in 10 mL of acetonitrile, 3 equivalents of potassium carbonate were added, and 1.2 equivalents of n-butyl iodide were added, and the reaction was carried out overnight at room temperature. After in-process control was completed, silica gel was immediately added to the reaction solution, stirred, and purified through a silica gel column to obtain compound 221-1, a white solid product of 690 mg. [ka]

[0113] (2) 690 mg of compound 221-1 was dissolved in 10 mL of tetrahydrofuran, 5 mL of water was added, and 2 equivalents of sodium hydroxide were added, and the mixture was reacted for 30 minutes. After in-process control was completed, the tetrahydrofuran was removed by spin. The reaction solution was acidified with dilute HCl and extracted twice with DCM. The organic phase was dried and spin-dried to obtain 600 mg of white solid compound 221-2. [ka]

[0114] (3) 90 mg of compound 221-2 was dissolved in 10 mL of DCM, 1.5 equivalents of triethylamine were added, followed by 1.2 equivalents of pyrazole compound 1-1, then 1.5 equivalents of EDCI and HATU were added respectively, and the mixture was reacted for 30 minutes. After in-process control was completed, the organic phase was washed with dilute hydrochloric acid, stirred, spin-dried, and purified through a silica gel column to obtain compound 221, a white solid product of 107 mg. [ka]

[0115] 11. Synthesis of Compound 261 (1) Compound 261-1 (12.1 g, 43 mmol, 1 equivalent) was dissolved in 100 mL of anhydrous tetrahydrofuran, and potassium tert-butoxide (130 mL, 0.13 mol, 3 equivalents, 1 M in THF) was slowly added in an ice bath. After stirring for 1 hour, methyl iodide (18.3 g, 0.13 mol, 3 equivalents) was added to the reaction solution, and the mixture was reacted at room temperature for 12 hours. The reaction was monitored until the starting materials had disappeared. The reaction solution was concentrated. The residue was made acidic, water was added, and the mixture was extracted three times with ethyl acetate, washed three times with saturated brine, dried on anhydrous sodium sulfate, and spin-dried to obtain 9.1 g of the crude product, compound 261-2 (71% yield). [ka]

[0116] (2) Compound 261-2 (297 mg, 1 mmol, 1 equivalent), Compound 261-3 (285 mg, 1.5 mmol, 1.5 equivalents), and cesium fluoride (302 mg, 2 mmol, 2 equivalents) were dissolved in 16 mL of dioxane and 2 mL of water, purged with nitrogen gas, a catalytic amount of Pd(dppf)Cl2 was added, purged with nitrogen gas three times, and the mixture was reacted at 100°C for 12 hours. The reaction was monitored until the starting materials disappeared. The reaction solution was concentrated, water was added, extracted three times with ethyl acetate, washed three times with saturated brine, dried on anhydrous sodium sulfate, purified through a silica gel column, and spin-dried to obtain 299 mg of Compound 261-4 (82.8% yield). [ka]

[0117] (3) Compound 261-4 (100 mg, 0.28 mmol, 1 equivalent), pyrazole compound 1-1 (44.5 mg, 0.34 mmol, 1.2 equivalents), and triethylamine (85 mg, 0.84 mmol, 3 equivalents) were dissolved in 10 mL of DCM, then Py-BOP (177 mg, 0.34 mmol, 1.2 equivalents) was added, and the mixture was reacted at room temperature for 1 hour. The reaction was monitored until the starting materials disappeared. Water was added to the reaction solution, extracted three times with DCM, washed three times with saturated brine, dried on anhydrous sodium sulfate, purified through a silica gel column, and spin-dried to obtain 89 mg of compound 261 (66.9% yield). [ka]

[0118] 12. Synthesis of Compound 340' (1) Compound 340-1 (4.6 g) was added to 50 mL of DCM, and PCC (2 equivalents) was added all at once. The mixture was reacted at room temperature for 2 hours. The solution was extracted with water and DCM. The organic phase was dried, concentrated, and purified by normal-phase chromatography to obtain compound 340-2 (2.8 g). [ka]

[0119] (2) Compound 340-2 (1 equivalent) was dissolved in 1000 mL of acetic acid and added to a 2000 mL necked flask. Ammonium acetate (45 g, 0.05 mol, 0.5 equivalents) was added, and nitromethane (200 g, 0.25 mol, 2.5 equivalents) was slowly added. The mixture was stirred at 100°C and allowed to react overnight. The reaction was monitored until the starting materials had disappeared. After the reaction, the system was treated with rotary evaporation to remove the solvent, and the mixture was purified through a silica gel column. The fraction was spin-dried to obtain compound 340-3 (54.9% yield). [ka]

[0120] (3) Compound 340-3 (1 equivalent) was dissolved in 500 mL of toluene, 10% (wt:wt) of catalyst (CAS: 941321-23-9) and dimethyl malonate (1.2 equivalents) were added, and the mixture was heated to 40°C and reacted for 12 hours. The reaction was monitored until the starting materials had disappeared. Water was added to the reaction solution, and it was extracted three times. The mixture was washed three times with saturated brine, dried on anhydrous sodium sulfate, and spin-dried to obtain compound 340-4 (90.9% yield). [ka]

[0121] (4) Compound 340-4 (1 equivalent) was dissolved in 600 mL of anhydrous methanol, nickel chloride hexahydrate (204 g, 72 mmol, 1 equivalent) was added, and sodium borohydride (97.7 g, 0.22 mol, 3 equivalents) was added all at once in an ice bath. The reaction was allowed to proceed at room temperature for 12 hours. The reaction was monitored until the starting materials had disappeared. The reaction solution was concentrated. Water was added to the residue, and it was acidified using hydrochloric acid. It was extracted three times with dichloromethane, washed three times with saturated brine, dried on anhydrous sodium sulfate, stirred, and purified through a silica gel column. The fraction was spin-dried to obtain compound 340-5 (39% yield). [ka]

[0122] (5) Compound 340-5 (1 equivalent) was dissolved in 300 mL of tetrahydrofuran and 100 mL of water, and sodium hydroxide (40.1 g, 0.16 mol, 3 equivalents) was added in an ice bath. The reaction was allowed to proceed at room temperature for 12 hours. The reaction was monitored until the starting materials had disappeared. The reaction solution was concentrated. The residue was made acidic, water was added, and the solution was extracted three times with ethyl acetate, washed three times with saturated brine, dried on anhydrous sodium sulfate, and spin-dried to obtain compound 340-6 (85.4% yield). [ka]

[0123] (6) Py-BOP (1.5 equivalents), compound 1-1 (1.5 equivalents), and triethylamine (2 equivalents) were added to a DCM solution (100 mL) of compound 340-6 (1 equivalent), and the mixture was reacted at room temperature for 1 hour. The reaction was monitored until the starting materials disappeared. Water was added to the reaction solution, and the mixture was extracted three times and washed three times with saturated brine. The organic phase was dried on anhydrous sodium sulfate, purified through a silica gel column, and spin-dried to obtain compound 340' (50% yield). [ka]

[0124] 13. Synthesis of Compound 411' (1) Compound 411-1 (1 equivalent), compound 411-2 (1.2 equivalents), K2CO3 (3 equivalents), and 4,5-bis(diphenylphosphin)-9,9-dimethylxanthene (0.1 equivalent) were dissolved in toluene, substituted with nitrogen gas, and tris(dibenzylideneacetone)dipalladium (0.1 equivalent) was added. The mixture was again substituted with nitrogen gas and reacted for 12 hours. The reaction solution was filtered through diatomaceous earth. The organic phase was extracted with water and ethyl acetate. The organic phase was collected and spin-dried to remove the solvent and obtain the crude product, compound 411-3. [ka]

[0125] (2) Iron powder (3 equivalents) and ammonium chloride (3 equivalents) were added to a solution of compound 411-3 (1 equivalent) (EtOH:H2O=3:1) and reacted at 80°C. The reaction solution was filtered through diatomaceous earth to remove the iron powder and extracted with EA. The organic phase was dried on anhydrous sodium sulfate and concentrated under reduced pressure to obtain compound 411-4. [ka]

[0126] (3) Py-BOP (1.5 equivalents), compound 411-4 (1.5 equivalents), and triethylamine (2 equivalents) were added to a DCM solution of compound 160-6 (1 equivalent) and stirred at room temperature. Water was added for extraction. The organic phase was dried over anhydrous sodium sulfate, silica gel powder was added, and the mixture was concentrated by vacuum concentration, rotated and evaporated to a dry state, and then normal-phase purification (mobile phase was petroleum ether / ethyl acetate = 2 / 3) was performed to obtain compound 411' (30% yield). [ka]

[0127] 14. Synthesis of Compound 451' Compound 117' (0.10 g, 1 equivalent) and Lawson's reagent (0.36 g, 3 equivalents) were added to 15 mL of toluene in a 50 mL round-bottom flask and reacted at 100 °C for 30 minutes. After the reaction was complete, the reaction solution was concentrated under reduced pressure to remove the solvent, and purified by silica gel column chromatography to obtain compound 451' (40 mg, 95% purity, 36% yield), a yellow solid product. [ka]

[0128] Evaluation of biological activity: (1) Seedling stage sealing experiment for water sowing: The activity level criteria (i.e., growth control rate) for plant damage are as follows: Level 9: Completely dead; Level 8: Growth control rate between 90% and 100%; Level 7: Growth control rate between 80% and 90%; Level 6: Growth control rate between 70% and 80%; Level 5: Growth control rate between 50% and 70%; Level 4: Growth control rate between 30% and 50%; Level 3: Growth control rate between 20% and 30%; Level 2: Growth control rate between 10% and 20%; Level 1: Growth control rate of less than 10%; Level 0: No effect.

[0129] The growth control rate mentioned above is the fresh weight control rate.

[0130] Seeds of Echinochloa crusgalli, Echinochloa phyllopogon, Digitalia sanguinalis, and Huaidao (a rice cultivar) were scattered on the surface of pots filled with soil and completely covered with soil. The well-prepared pots were then placed in a growing box filled with water to a suitable height to keep the soil in the pots moist. The test compounds of the present invention were individually dissolved in acetone, then diluted in a solution of a specific concentration using a specific amount of water, and sprayed using a spray tower. The plants were placed on a greenhouse seedbed and grown for 15 days, and the experimental results were then collected. The compounds were applied in three consecutive applications at 120, 60, 30, and 15 g ai / ha, and the results were averaged. Representative data are listed in Table 3.

[0131] [Table 3-1] [Table 3-2] [Table 3-3] [Table 3-4] [Table 3-5] [Table 3-6] [Table 3-7] [Table 3-8] [Table 3-9]

[0132] (2) Evaluation of safety in transplanted rice and evaluation of control effect on weeds in paddy fields:

[0133] After placing paddy field soil into pots measuring 1 / 1,000,000 hectares, seeds of Echinochloa crusgalli and Echinochloa phyllopogon were sown, gently covered with soil, and then left to stand in a greenhouse with a reservoir of water to a depth of 0.5–1 cm. The reservoir was then maintained at a depth of 3–4 cm. When Echinochloa crusgalli and Echinochloa phyllopogon reached the 0.5-leaf stage, aqueous dilutions of the compound of the present invention, formulated according to a conventional formulation method, were uniformly added dropwise using a pipette to a specified effective volume for treatment.

[0134] Additionally, after placing the mixture in pots representing 1 / 1,000,000 hectares of land, the paddy field soil was leveled and water was maintained at a depth of 3-4 cm. Three-leaf rice plants (Japonica rice) were transplanted the following day to a transplanting depth of 3 cm. Five days after transplanting, the plants were treated with the compound of the present invention using the same method as described above.

[0135] The development of Echinochloa crusgalli and Echinochloa phyllopogon 14 days after drug treatment, and the development of rice 21 days after drug treatment were observed with the naked eye. The effects were evaluated according to the above criteria for activity levels. Many compounds exhibited excellent activity and selectivity.

[0136] (3) Fungicidal activity assay: Petri dish method: The drug was dissolved in acetone, diluted with sterile water, and set to different mass concentrations according to its activity. Under sterile operating conditions, the pre-dissolved sterile culture medium was quantitatively added to sterile flasks according to the test treatment. The drug solution was quantitatively aspirated from low to high concentrations and added to the flasks and shaken wells, respectively. Next, equal volumes of the solution were poured into three 6 cm diameter petri dishes to prepare drug-containing plates with corresponding concentrations. In the test, a treatment without the drug was set as a blank control, and each treatment was repeated three times. Under sterile conditions, a 3 mm diameter fungal cake was excised from the edge of a cultured pathogen colony using a sterile hole puncher. The fungal cake was inoculated into the center of the drug-containing plate using an inoculation device with the mycelium facing upwards, covered with a plate cover, and incubated in a 25°C incubator. After 4 days, the growth of the pathogen mycelium was examined in accordance with the fungal growth in the blank control petri dish. The diameter of the colonies was measured in millimeters (mm) using a caliper. Each colony was measured vertically once for diameter using the cross-pollination method, and then the average was calculated. Based on the results, the mycelial growth inhibition rate for each treatment concentration in the target fungus was calculated according to equations (1) and (2). The unit was percentage (%). D=D1-D2…………………………………………(1) (In the formula, D is the increase in colony diameter; D1 is the colony diameter; and D2 is the fungal cake diameter.)

number

[0137] [Table 4]

[0138] (4) Insecticidal activity assay: Spray method: Technical materials were weighed, dissolved in acetone, and the chemical solution was diluted with distilled water to different concentrations. Second-instar Spodoptera frugiperda or third-instar Mythimna separata test insects were selected and reared indoors under consistent physiological conditions. Ten test insects were collected in each petri dish. Two 2 cm long corn leaves were placed in the petri dish, and spraying was performed using a spray tower. Each administration was repeated three times, with the corresponding concentration of acetone used as a control. After drug application, the insects were transferred and reared under conditions of 25°C and 60% humidity. Results were examined 48 hours after drug application, and the number of deaths per treatment was collected. Mortality was calculated according to the following formula: Mortality (%) = (Number of dead insects / Number of test insects) × 100. Representative data are shown in Table 5.

[0139] [Table 5]

[0140] (5) Activity assay of the composition: The required active ingredient B was purchased from a reagent company or technical materials manufacturer, or synthesized by conventional methods. All technical materials were dissolved in acetone solvent and diluted with an aqueous solution of 0.1% Tween® 80 emulsifier (should be used immediately after dilution).

[0141] (A) Soil sealing treatment (S): Weeds were cultivated in a greenhouse with controllable sunlight at 20-30°C, under natural light and relative humidity of 57-72%. The soil was loam with an organic matter content of 1.63%, a pH of 7.1, 84.3 mg / kg of alkaline hydrolyzable nitrogen, 38.5 mg / kg of rapidly available phosphorus, and 82.1 mg / kg of rapidly available potassium. The test soil was quantitatively filled to 3 / 4 of the pot, and then watered from the bottom of the pot to completely moisten the soil until saturated. To accelerate the germination of the test weed seeds, they were then uniformly and quantitatively scattered on the soil surface, covered with 0.5-1 cm of soil according to the size of the seeds, and prepared for use 72 hours after scattering.

[0142] Each treatment was repeated four times. In each treatment, four pots were treated with 20 weed seeds per pot.

[0143] The seeds were planted in a 20cm x 30cm square box. Water was added to a depth of 2-3cm after sowing, then the fungicide was injected using a syringe, mixed evenly, and left to dry naturally for 2 days. The soil was then kept moist.

[0144] (B) Post-emergence spray treatment of stems and leaves (F): Weeds were cultivated using a pot cultivation method. 180 x 140 mm plastic planters containing air-dried, sifted topsoil (up to 4 / 5 of the pot's height) collected from fields were placed in an enamel pot, ensuring the soil had an initial moisture content of 20%. Weed seeds with plump, uniform granules were selected, immersed in 25°C lukewarm water for 6 hours, and then germination was accelerated in a 28°C biochemical incubator (in darkness). The newly germinated weed seeds were evenly distributed on the soil surface and then covered with 0.5-1 cm of soil according to seed size.

[0145] Weeds were grown in a greenhouse with controllable sunlight at 20-30°C, under natural light and relative humidity of 57-72%. The soil was loamy with an organic matter content of 1.63%, a pH of 7.1, 84.3 mg / kg of alkali-hydrolyzable nitrogen, 38.5 mg / kg of rapidly available phosphorus, and 82.1 mg / kg of rapidly available potassium.

[0146] Each process was repeated four times. In each round, three pots containing 20 weed seeds each were processed.

[0147] The drug was applied only once in total during the experiment. At the 1.5-2 leaf stage, weeds were thinned to maintain 10 plants per pot. 30 plants were kept in each treatment, and cultivation was then continued until the 3-4 leaf stage for further treatment.

[0148] Well-cultivated test material 0.5m 2 The plants were evenly placed on the platform and sprayed onto the leaves using a 3WP-2000 type walking spray tower with a dosage of 450 kg / ha and a spray pressure of 0.3 MPa. After spraying all of the drug solution, the air valve was closed. After 30 seconds, the spray tower door was opened and the plant pots were removed. Next, the air valve was opened and the spray tubes were cleaned by spraying 50 mL of water. The test materials were transferred and cultivated in a greenhouse using conventional methods after treatment.

[0149] (C) Data investigation and statistical analysis A method was used to determine the absolute number. The entire seedling of a living weed was cut along the soil surface with a blade, and the fresh weight of the weed was weighed using a chemical balance. For dead weeds, the fresh weight was considered to be 0.

[0150] The investigation was conducted only once, 21 days after the treatment.

[0151] The theoretical fresh weight inhibition rate for mixed combinations of each treatment was calculated using Gowing's method (E0 = X + YX * Y / 100), and the type of combined effect of these two combinations on weeds was evaluated by comparing them with the measured inhibition rate (E). The combined effect was synergistic when E-E0 > 10%; antagonistic when E-E0 < -10%; and additive when -10% ≤ E-E0 ≤ 10%. The optimal ratio was determined according to factors such as the actual control effect, herbicide characteristics, and formulation balance. In the 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. Statistical results are shown in Table 6.

[0152] [Table 6-1] [Table 6-2] [Table 6-3] [Table 6-4]

[0153] On the other hand, many of the compounds and compositions of the present invention exhibit good selectivity for grasses, such as Zoysia grasses, Bermuda grass, tall fescue, bluegrass, ryegrass, and seashore paspalum, and have been found through large-scale experiments to be able to prevent or eliminate many key grass weeds and broadleaf weeds. Experiments on sugarcane, soybeans, cotton, oil sunflowers, potatoes, fruit trees, and vegetables using different drug application methods have also demonstrated excellent selectivity and commercial value. Furthermore, many of the compounds and compositions of the present invention have good regulatory activity against different types of fungi, including the orders Ascomycetes, Basidiomycetes, Deuteromycetes, and Oomycetes, as well as good regulatory activity against agricultural pests, such as lepidopteran insects (e.g., Spodoptera frugiperda, Mythimna separata), and thus possess certain commercial value.

[0154] Finally, it should be noted that the embodiments described above are merely examples of the technical solutions of the present invention and do not impose any limitations. Although the present invention has been described in detail with reference to preferred embodiments, it should be understood by those skilled in the art that the technical solutions of the present invention can be modified or replaced by equivalents without departing from the spirit and scope of the present invention.

Claims

1. The substituted pyrrolidone compound is as shown in general formula I: 【Chemistry 1】 (In the formula, Q is, 【Chemistry 2】 It represents; X and Y are each independently hydrogen, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, cycloalkyl, cycloalkylalkyl, aryl, arylalkyl, heterocyclyl, heterocyclylalkyl, hydroxyl, hydroxylalkyl, mercapto, mercaptoalkyl, nitro, cyanoalkyl, formyl, trialkylsilyl, -N(R ２１ ), -OR ２ , -SR ２２ , -(CO)R ２２、 , -(CO)OR ２２、 , -(SO ２２、 ), -SR ２ , -(SO)R ２２、 , -(SO ２２、 ), -(SO' ２ ), -N(R ２１ ), ２ , -alkylene-N(R ２１ ), ２ , -alkylene-OR ２２ , -alkylene-SR ２２ , -alkylene-(CO)R ２２ , -alkylene-(CO)OR ２２ , -alkylene-(SO ２ ), -SR ２２ , or -alkylene-(SO" ２ ), -N(R ２１ ), ２ ; Z is alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, cycloalkyl, cycloalkylalkyl, aryl, arylalkyl, heterocyclyl, heterocyclylalkyl, hydroxyl, hydroxylalkyl, mercapto, mercaptoalkyl, nitro, cyanoalkyl, formyl, trialkylsilyl, -N(R) ２１ ) ２ , -OR ２２ , -SR ２２ ,-(SO)R ２２ ,-(CO)R ２２ , - (CO) OR ２２ ,-(SO ２ ) R ２２ ,-(SO ２ )N(R ２１ ) ２ ,-alkylene-N(R ２１ ) ２ , -Alkilen-OR ２２ ,-Alkilen-SR ２２ ,-alkylene-(CO)R ２２ ,-alkylene-(CO)OR ２２ ,-Alkilen-(SO ２ ) R ２２ , or -alkylene-(SO ２ )N(R ２１ ) ２ It represents; W １ and W ２ Each of these independently represents either O or S; R ６ is represented by hydrogen, hydroxyl, halogen, alkyl, cycloalkyl, alkoxy, or haloalkyl; R ７ This includes hydrogen, halogen, nitro, cyano, formyl, carboxyl, hydroxyl, hydroxylalkyl, mercapto, mercaptoalkyl, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, -OR ２２ , -SR ２２ ,-(SO)R ２２ ,-(SO ２ ) R ２２ , -CR ２３ = N-O-R ２２ , -Alkilen-OR ２２ ,-Alkilen-SR ２２ ,-Alkilen-(SO ２ ) R ２２ cycloalkyl, cycloalkenyl, aryl, heterocyclyl, -(CO)R ２２ ,-(CO)N(R ２１ ) ２ , - (CO) OR ２２ , -N(R ２１ ) ２ ,-alkylene-(CO)R ２２ ,-alkylene-(CO)N(R ２１ ) ２ ,-alkylene-(CO)OR ２２ , or -alkylene-N(R ２１ ) ２ It represents; R ８ represents hydrogen, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, cycloalkyl, or cycloalkylalkyl; R １ 、R ２ 、R ３ 、R ４ and R ５ are each independently hydrogen, halogen, nitro, cyano, cyanothio, hydroxyl, mercapto, carboxyl, sulfo, formyl, haloformyl, azide, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, heterocyclyl, aryl, -N(R ２１ ), -(CO)N(R ２ ), -O(CO)N(R ２１ ), -O(CS)N(R ２ ), -(SO ２１ ), -O(SO ２ ), -PO(OR ２１ ), -OR ２ ), -(CO)R ２ ), -SR ２１ ), -(SO)R ２ ), -(SO ２ ), -O(SO ２１ ), -PO(OR ２ ), -OR ２２ ), -(CO)R ２ ), -SR ２２ ), -(CO)R ２２ ), -SR ２２ ), -(SO)R ２２ ), -(SO ２ ), -Si(R ２２ ), -OR ２２ ), -O(CO)R ３ ), -O-(SO ２２ ), -S(CO)R ２ ), -(SO ２２ ), -O(CO)OR ２２ ), -(CO)(CO)OR ２ ), -(CO)OR ２２ ), -O-N=C(R ２２ [[ID=[72]]), -(CO)OR ２２ ), -(CO)OR ２２ ), -O-N=C(R ２３ ), -(CO)OR ２ ), -CR ２３ =N-OH, or -CR ２３ =N-O-R ２２ represents; said "alkyl", "alkenyl" or "alkynyl" is halogen, nitro, cyano, hydroxyl, mercapto, carboxyl, cycloalkyl, cycloalkenyl, heterocyclyl, aryl, -N(R ２１ ) ２ ,-(CO)N(R ２１ ) ２ , -O(CO)N(R ２１ ) ２ , -O(CS)N(R ２１ ) ２ ,-(SO ２ )N(R ２１ ) ２ , -O(SO ２ )N(R ２１ ) ２ , -OR ２２ ,-(CO)R ２２ , -SR ２２ ,-(SO)R ２２ ,-(SO ２ ) R ２２ , -O(CO)H, -O(CO)R ２２ , -O-(SO ２ ) R ２２ , - (CO) OR ２２ , -O(CO)OR ２２ , -Si(R ２２ ) ３ , -O(CO)(CO)OH, -O(CO)(CO)OR ２２ -O-alkylene-(CO)OH, and -O-alkylene-(CO)OR ２２ It may be replaced by at least one group selected from; R １１ Each of these is independently a halogen, nitro, cyano, cyanothio, hydroxyl, mercapto, carboxyl, sulfo, formyl, haloformyl, azide, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, heterocyclyl, aryl, -N(R) ２１ ) ２ ,-(CO)N(R ２１ ) ２ , -O(CO)N(R ２１ ) ２ , -O(CS)N(R ２１ ) ２ ,-(SO ２ )N(R ２１ ) ２ , -O(SO ２ )N(R ２１ ) ２ , -PO(OR ２２ ) ２ , -OR ２２ ,-(CO)R ２２ , -SR ２２ ,-(SO)R ２２ ,-(SO ２ ) R ２２ , -Si(R ２２ ) ３ , -O(CO)R ２２ , -O-(SO ２ ) R ２２ , -S(CO)R ２２ ,-(SO ２ ) OR ２２ , -O(CO)OR ２２ , -(CO)(CO)OR ２２ , - (CO) OR ２２ -O-N=C(R ２３ ) ２ , -CR ２３ = N-OH, or -CR ２３ = N-O-R ２２ The terms "alkyl", "alkenyl", or "alkynyl" refer to halogen, nitro, cyano, hydroxyl, mercapto, carboxyl, cycloalkyl, cycloalkenyl, heterocyclyl, aryl, -N(R) ２１ ) ２ ,-(CO)N(R ２１ ) ２ , -O(CO)N(R ２１ ) ２ , -O(CS)N(R ２１ ) ２ ,-(SO ２ )N(R ２１ ) ２ , -O(SO ２ )N(R ２１ ) ２ , -OR ２２ ,-(CO)R ２２ , -SR ２２ ,-(SO)R ２２ ,-(SO ２ ) R ２２ , -O(CO)H, -O(CO)R ２２ , -O-(SO ２ ) R ２２ , - (CO) OR ２２ , -O(CO)OR ２２ , -Si(R ２２ ) ３ , -O(CO)(CO)OH, -O(CO)(CO)OR ２２ -O-alkylene-(CO)OH, and -O-alkylene-(CO)OR ２２ It may be replaced by at least one group selected from; R ２１ Each is independently hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, aryl, heterocyclyl, -OR ２２ ,-(CO)R ２２ , - (CO) OR ２２ ,-alkylene-(CO)OR ２２ ,-(SO ２ ) R ２２ ,-(SO ２ ) OR ２２ ,-Alkilen-(SO ２ ) R ２２ ,-(CO)N(R ２４ ) ２ , or - (SO ２ )N(R ２４ ) ２ It represents; R ２２ Each of these independently represents an alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, aryl, or heterocyclyl, wherein the "alkyl," "alkenyl," or "alkynyl" can be a halogen, cyano, trialkylsilyl, cycloalkyl, cycloalkenyl, aryl, heterocyclyl, or -OR ２５ , -SR ２５ , -O(CO)R ２５ ,-(CO)R ２５ , - (CO) OR ２５ , and -O(CO)OR ２５ It may be replaced by at least one group selected from; R ２３ Each of these independently represents hydrogen, halogen, alkoxy, alkoxyalkyl, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl, cycloalkenylalkyl, aryl, arylalkyl, heterocyclyl, or heterocyclylalkyl; R ２４ Each independently represents hydrogen, alkyl, alkenyl, alkynyl, alkoxy, alkylsulfonyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl, or cycloalkenylalkyl; or N(R) ２１ ) ２ and N(R ２４ ) ２ Each of these independently represents a heterocyclyl having a nitrogen atom at position 1; R ２５ Each independently represents hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, haloalkyl, haloalkenyl, haloalkynyl, phenyl, or: halogen, cyano, nitro, alkyl, haloalkyl, alkoxy, haloalkoxy, alkoxycarbonyl, alkylthio, alkylsulfonyl, phenoxy, and phenyl substituted with at least one group selected from halogen, cyano, nitro, alkyl, haloalkyl, alkoxy, and haloalkoxy; The above terms "cycloalkyl," "cycloalkenyl," "heterocyclyl," or "aryl" are oxo, halogen, cyano, nitro, alkyl, alkenyl, alkynyl, cycloalkyl, haloalkyl, haloalkenyl, haloalkynyl, halocycloalkyl, alkyl-substituted cycloalkyl, -OR １０ , -SR １０ , - (CO) OR １０ ,-(SO ２ ) R １０ , -N(R １０ ) ２ and -O-alkylene-(CO)OR １０ It may be substituted with at least one group selected from -OCH, or two adjacent carbon atoms may be unsubstituted or substituted with a halogen. ２ CH ２ - or - OCH ２ It forms a fused ring with O-; R １０ Each of these independently represents hydrogen, alkyl, haloalkyl, phenyl, or phenyl substituted with at least one group selected from halogen, cyano, nitro, alkyl, haloalkyl, alkoxycarbonyl, alkylthio, alkylsulfonyl, alkoxy, and haloalkoxy.

2. X and Y are independently hydrogen, 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, aryl, aryl-C1-C8 alkyl, heterocyclyl, heterocyclyl-C1-C8 alkyl, hydroxyl, hydroxyl-C1-C8 alkyl, mercapto, mercapto-C1-C8 alkyl, nitro, cyano-C1-C8 alkyl, formyl, tri-C1-C8 alkylsilyl, -N(R) ２１ ) ２ , -OR ２２ , -SR ２２ ,-(SO)R ２２ ,-(CO)R ２２ , - (CO) OR ２２ ,-(SO ２ ) R ２２ ,-(SO ２ )N(R ２１ ) ２ ,-(C1-C8 alkylene)-N(R ２１ ) ２ , -(C1-C8 alkylene)- OR ２２ ,-(C1-C8 alkylene)-SR ２２ ,-(C1-C8 alkylene)-(CO)R ２２ , -(C1-C8 alkylene)-(CO)OR ２２ , -(C1-C8 alkylene)-(SO ２ ) R ２２ , or -(C1-C8 alkylene)-(SO ２ )N(R ２１ ) ２ It represents; Z is 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, aryl, aryl-C1-C8 alkyl, heterocyclyl, heterocyclyl-C1-C8 alkyl, hydroxyl, hydroxyl-C1-C8 alkyl, mercapto, mercapto-C1-C8 alkyl, nitro, cyano-C1-C8 alkyl, formyl, tri-C1-C8 alkylsilyl, -N(R) ２１ ) ２ , -OR ２２ , -SR ２２ ,-(SO)R ２２ ,-(CO)R ２２ , - (CO) OR ２２ ,-(SO ２ ) R ２２ ,-(SO ２ )N(R ２１ ) ２ ,-(C1-C8 alkylene)-N(R ２１ ) ２ , -(C1-C8 alkylene)- OR ２２ ,-(C1-C8 alkylene)-SR ２２ ,-(C1-C8 alkylene)-(CO)R ２２ , -(C1-C8 alkylene)-(CO)OR ２２ , -(C1-C8 alkylene)-(SO ２ ) R ２２ , or -(C1-C8 alkylene)-(SO ２ )N(R ２１ ) ２ It represents; R ６ is represented by hydrogen, hydroxyl, halogen, C1-C8 alkyl, C3-C8 cycloalkyl, C1-C8 alkoxy, or halo-C1-C8 alkyl; R ７ This includes hydrogen, halogen, nitro, cyano, formyl, carboxyl, hydroxyl, hydroxyl C1-C8 alkyl, mercapto, mercapto C1-C8 alkyl, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, halo C1-C8 alkyl, halo C2-C8 alkenyl, halo C2-C8 alkynyl, -OR ２２ , -SR ２２ ,-(SO)R ２２ ,-(SO ２ ) R ２２ , -CR ２３ = N-O-R ２２ , -(C1-C8 alkylene)- OR ２２ ,-(C1-C8 alkylene)-SR ２２ , -(C1-C8 alkylene)-(SO ２ ) R ２２ C3-C8 cycloalkyl, C3-C8 cycloalkenyl, aryl, heterocyclyl, -(CO)R ２２ ,-(CO)N(R ２１ ) ２ , - (CO) OR ２２ , -N(R ２１ ) ２ ,-(C1-C8 alkylene)-(CO)R ２２ ,-(C1-C8 alkylene)-(CO)N(R ２１ ) ２ , -(C1-C8 alkylene)-(CO)OR ２２ , or -(C1-C8 alkylene)-N(R ２１ ) ２ It represents; R ８ is represented by hydrogen, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, halo-C1-C8 alkyl, halo-C2-C8 alkenyl, halo-C2-C8 alkynyl, C3-C8 cycloalkyl, or C3-C8 cycloalkyl-C1-C8 alkyl; R １ , R ２ , R ３ , R ４ and R ５ Each of these is independently hydrogen, halogen, nitro, cyano, cyanothio, hydroxyl, mercapto, carboxyl, sulfo, formyl, haloformyl, azide, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkenyl, heterocyclyl, aryl, -N(R) ２１ ) ２ ,-(CO)N(R ２１ ) ２ , -O(CO)N(R ２１ ) ２ , -O(CS)N(R ２１ ) ２ ,-(SO ２ )N(R ２１ ) ２ , -O(SO ２ )N(R ２１ ) ２ , -PO(OR ２２ ) ２ , -OR ２２ ,-(CO)R ２２ , -SR ２２ ,-(SO)R ２２ ,-(SO ２ ) R ２２ , -Si(R ２２ ) ３ , -O(CO)R ２２ , -O-(SO ２ ) R ２２ , -S(CO)R ２２ ,-(SO ２ ) OR ２２ , -O(CO)OR ２２ , -(CO)(CO)OR ２２ , - (CO) OR ２２ -O-N=C(R ２３ ) ２ , -CR ２３ = N-OH, or -CR ２３ = N-O-R ２２ The terms "C1-C8 alkyl", "C2-C8 alkenyl", or "C2-C8 alkynyl" represent halogen, nitro, cyano, hydroxyl, mercapto, carboxyl, C3-C8 cycloalkyl, C3-C8 cycloalkenyl, heterocyclyl, aryl, -N(R) ２１ ) ２ ,-(CO)N(R ２１ ) ２ , -O(CO)N(R ２１ ) ２ , -O(CS)N(R ２１ ) ２ ,-(SO ２ )N(R ２１ ) ２ , -O(SO ２ )N(R ２１ ) ２ , -OR ２２ ,-(CO)R ２２ , -SR ２２ ,-(SO)R ２２ ,-(SO ２ ) R ２２ , -O(CO)H, -O(CO)R ２２ , -O-(SO ２ ) R ２２ , - (CO) OR ２２ , -O(CO)OR ２２ , -Si(R ２２ ) ３ , -O(CO)(CO)OH, -O(CO)(CO)OR ２２ -O-(C1-C8 alkylene)-(CO)OH, and -O-(C1-C8 alkylene)-(CO)OR ２２ It may be replaced by at least one group selected from; R １１ These are, independently, halogen, nitro, cyano, cyanothio, hydroxyl, mercapto, carboxyl, sulfo, formyl, haloformyl, azide, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkenyl, heterocyclyl, aryl, -N(R) ２１ ) ２ ,-(CO)N(R ２１ ) ２ , -O(CO)N(R ２１ ) ２ , -O(CS)N(R ２１ ) ２ ,-(SO ２ )N(R ２１ ) ２ , -O(SO ２ )N(R ２１ ) ２ , -PO(OR ２２ ) ２ , -OR ２２ ,-(CO)R ２２ , -SR ２２ ,-(SO)R ２２ ,-(SO ２ ) R ２２ , -Si(R ２２ ) ３ , -O(CO)R ２２ , -O-(SO ２ ) R ２２ , -S(CO)R ２２ ,-(SO ２ ) OR ２２ , -O(CO)OR ２２ , -(CO)(CO)OR ２２ , - (CO) OR ２２ -O-N=C(R ２３ ) ２ , -CR ２３ = N-OH, or -CR ２３ = N-O-R ２２ Represents; "C1-C8 alkyl", "C2-C8 alkenyl", or "C2-C8 alkynyl" are halogens, nitro, cyano, hydroxyl, mercapto, carboxyl, C3-C8 cycloalkyl, C3-C8 cycloalkenyl, heterocyclyl, aryl, -N(R) ２１ ) ２ ,-(CO)N(R ２１ ) ２ , -O(CO)N(R ２１ ) ２ , -O(CS)N(R ２１ ) ２ ,-(SO ２ )N(R ２１ ) ２ , -O(SO ２ )N(R ２１ ) ２ , -OR ２２ ,-(CO)R ２２ , -SR ２２ ,-(SO)R ２２ ,-(SO ２ ) R ２２ , -O(CO)H, -O(CO)R ２２ , -O-(SO ２ ) R ２２ , - (CO) OR ２２ , -O(CO)OR ２２ , -Si(R ２２ ) ３ , -O(CO)(CO)OH, -O(CO)(CO)OR ２２ -O-(C1-C8 alkylene)-(CO)OH, and -O-(C1-C8 alkylene)-(CO)OR ２２ It may be replaced by at least one group selected from; R ２１ Each of these is independently hydrogen, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkenyl, aryl, heterocyclyl, -OR ２２ ,-(CO)R ２２ , - (CO) OR ２２ , -(C1-C8 alkylene)-(CO)OR ２２ ,-(SO ２ ) R ２２ ,-(SO ２ ) OR ２２ , -(C1-C8 alkylene)-(SO ２ ) R ２２ ,-(CO)N(R ２４ ) ２ , or - (SO ２ )N(R ２４ ) ２ It represents; R ２２ Each of these independently represents a C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkenyl, aryl, or heterocyclyl, wherein the "C1-C8 alkyl," "C2-C8 alkenyl," or "C2-C8 alkynyl" can be a halogen, cyano, triC1-C8 alkylsilyl, C3-C8 cycloalkyl, C3-C8 cycloalkenyl, aryl, heterocyclyl, or -OR ２５ , -SR ２５ , -O(CO)R ２５ ,-(CO)R ２５ , - (CO) OR ２５ , and -O(CO)OR ２５ It may be replaced by at least one group selected from; R ２３ Each of these independently represents hydrogen, halogen, C1-C8 alkoxy, C1-C8 alkoxy, C1-C8 alkyl, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkyl, C1-C8 alkyl, C3-C8 cycloalkenyl, C3-C8 cycloalkenyl C1-C8 alkyl, aryl, aryl C1-C8 alkyl, heterocyclyl, or heterocyclyl C1-C8 alkyl; R ２４ Each independently represents hydrogen, 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 N(R) ２１ ) ２ and N(R ２４ ) ２ Each of these independently represents a heterocyclyl having a nitrogen atom at position 1; R ２５ Each independently represents a phenyl substituted with at least one group selected from hydrogen, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, halo-C1-C8 alkyl, halo-C2-C8 alkenyl, halo-C2-C8 alkynyl, phenyl, or the following: halogen, cyano, nitro, C1-C8 alkyl, halo-C1-C8 alkyl, C1-C8 alkoxy, halo-C1-C8 alkoxy, C1-C8 alkoxycarbonyl, C1-C8 alkylthio, C1-C8 alkylsulfonyl, phenoxy, and phenyl substituted with at least one group selected from halogen, cyano, nitro, C1-C8 alkyl, halo-C1-C8 alkyl, C1-C8 alkoxy, and halo-C1-C8 alkoxy; The above "C3-C8 cycloalkyl", "C3-C8 cycloalkenyl", "heterocyclyl", or "aryl" are 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 １０ , -SR １０ , - (CO) OR １０ ,-(SO ２ ) R １０ , -N(R １０ ) ２ and -O-(C1-C8 alkylene)-(CO)OR １０ It may be substituted with at least one group selected from -OCH, or two adjacent carbon atoms may be unsubstituted or substituted with a halogen. ２ CH ２ - or - OCH ２ It forms a fused ring with O-; R １０ Each independently represents a phenyl substituted with at least one group selected from hydrogen, C1-C8 alkyl, halo-C1-C8 alkyl, phenyl, or 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. The substituted pyrrolidone compound according to claim 1, characterized in that...

3. X and Y are independently hydrogen, 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, aryl, aryl-C1-C6 alkyl, heterocyclyl, heterocyclyl-C1-C6 alkyl, hydroxyl, hydroxyl-C1-C6 alkyl, mercapto, mercapto-C1-C6 alkyl, nitro, cyano-C1-C6 alkyl, formyl, tri-C1-C6 alkylsilyl, -N(R) ２１ ) ２ , -OR ２２ , -SR ２２、 - (SO)R ２２、 - (CO)R ２２ , - (CO) OR ２２ ,-(SO ２ ) R ２２、 - (SO ２ )N(R ２１ ) ２ ,-(C1-C6 alkylene)-N(R ２１ ) ２ , -(C1-C6 alkylene)- OR ２２ ,-(C1-C6 alkylene)-SR ２２ ,-(C1-C6 alkylene)-(CO)R ２２ ,-(C1-C6 alkylene)-(CO)OR ２２ , -(C1-C6 alkylene)-(SO ２ ) R ２２ , or -(C1-C6 alkylene)-(SO ２ )N(R ２１ ) ２ It represents; Z is 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, aryl, aryl-C1-C6 alkyl, heterocyclyl, heterocyclyl-C1-C6 alkyl, hydroxyl, hydroxyl-C1-C6 alkyl, mercapto, mercapto-C1-C6 alkyl, nitro, cyano-C1-C6 alkyl, formyl, tri-C1-C6 alkylsilyl, -N(R) ２１ ) ２ , -OR ２２ , -SR ２２ ,-(SO)R ２２ ,-(CO)R ２２ , - (CO) OR ２２ ,-(SO ２ ) R ２２ ,-(SO ２ )N(R ２１ ) ２ ,-(C1-C6 alkylene)-N(R ２１ ) ２ , -(C1-C6 alkylene)- OR ２２ ,-(C1-C6 alkylene)-SR ２２ ,-(C1-C6 alkylene)-(CO)R ２２ ,-(C1-C6 alkylene)-(CO)OR ２２ , -(C1-C6 alkylene)-(SO ２ ) R ２２ , or -(C1-C6 alkylene)-(SO ２ )N(R ２１ ) ２ It represents; R ６ is represented by hydrogen, hydroxyl, halogen, C1-C6 alkyl, C3-C6 cycloalkyl, C1-C6 alkoxy, or halo-C1-C6 alkyl; R ７ This includes hydrogen, halogen, nitro, cyano, formyl, carboxyl, hydroxyl, hydroxyl C1-C6 alkyl, mercapto, mercapto C1-C6 alkyl, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, halo C1-C6 alkyl, halo C2-C6 alkenyl, halo C2-C6 alkynyl, -OR ２２ , -SR ２２ ,-(SO)R ２２ ,-(SO ２ ) R ２２ , -CR ２３ = N-O-R ２２ , -(C1-C6 alkylene)- OR ２２ ,-(C1-C6 alkylene)-SR ２２ , -(C1-C6 alkylene)-(SO ２ ) R ２２ C3-C6 cycloalkyl, C3-C6 cycloalkenyl, aryl, heterocyclyl, -(CO)R ２２ ,-(CO)N(R ２１ ) ２ , - (CO) OR ２２ , -N(R ２１ ) ２ ,-(C1-C6 alkylene)-(CO)R ２２ ,-(C1-C6 alkylene)-(CO)N(R ２１ ) ２ ,-(C1-C6 alkylene)-(CO)OR ２２ , or -(C1-C6 alkylene)-N(R ２１ ) ２ It represents; R ８ is represented by hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, halo-C1-C6 alkyl, halo-C2-C6 alkenyl, halo-C2-C6 alkynyl, C3-C6 cycloalkyl, or C3-C6 cycloalkyl-C1-C6 alkyl; R １ , R ２ , R ３ , R ４ and R ５ Each of these is independently hydrogen, halogen, nitro, cyano, cyanothio, hydroxyl, mercapto, carboxyl, sulfo, formyl, haloformyl, azide, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkenyl, heterocyclyl, aryl, -N(R) ２１ ) ２ ,-(CO)N(R ２１ ) ２ , -O(CO)N(R ２１ ) ２ , -O(CS)N(R ２１ ) ２ ,-(SO ２ )N(R ２１ ) ２ , -O(SO ２ )N(R ２１ ) ２ , -PO(OR ２２ ) ２ , -OR ２２ ,-(CO)R ２２ , -SR ２２ ,-(SO)R ２２ ,-(SO ２ ) R ２２ , -Si(R ２２ ) ３ , -O(CO)R ２２ , -O-(SO ２ ) R ２２ , -S(CO)R ２２ ,-(SO ２ ) OR ２２ , -O(CO)OR ２２ , -(CO)(CO)OR ２２ , - (CO) OR ２２ -O-N=C(R ２３ ) ２ , -CR ２３ = N-OH, or -CR ２３ = N-O-R ２２ The terms "C1-C6 alkyl", "C2-C6 alkenyl", or "C2-C6 alkynyl" represent halogen, nitro, cyano, hydroxyl, mercapto, carboxyl, C3-C6 cycloalkyl, C3-C6 cycloalkenyl, heterocyclyl, aryl, -N(R) ２１ ) ２ ,-(CO)N(R ２１ ) ２ , -O(CO)N(R ２１ ) ２ , -O(CS)N(R ２１ ) ２ ,-(SO ２ )N(R ２１ ) ２ , -O(SO ２ )N(R ２１ ) ２ , -OR ２２ ,-(CO)R ２２ , -SR ２２ ,-(SO)R ２２ ,-(SO ２ ) R ２２ , -O(CO)H, -O(CO)R ２２ , -O-(SO ２ ) R ２２ , - (CO) OR ２２ , -O(CO)OR ２２ , -Si(R ２２ ) ３ , -O(CO)(CO)OH, -O(CO)(CO)OR ２２ -O-(C1-C6 alkylene)-(CO)OH, and -O-(C1-C6 alkylene)-(CO)OR ２２ It may be replaced by at least one group selected from; R １１ These are, independently, halogen, nitro, cyano, cyanothio, hydroxyl, mercapto, carboxyl, sulfo, formyl, haloformyl, azide, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkenyl, heterocyclyl, aryl, -N(R) ２１ ) ２ ,-(CO)N(R ２１ ) ２ , -O(CO)N(R ２１ ) ２ , -O(CS)N(R ２１ ) ２ ,-(SO ２ )N(R ２１ ) ２ , -O(SO ２ )N(R ２１ ) ２ , -PO(OR ２２ ) ２ , -OR ２２ ,-(CO)R ２２ , -SR ２２ ,-(SO)R ２２ ,-(SO ２ ) R ２２ , -Si(R ２２ ) ３ , -O(CO)R ２２ , -O-(SO ２ ) R ２２ , -S(CO)R ２２ ,-(SO ２ ) OR ２２ , -O(CO)OR ２２ , -(CO)(CO)OR ２２ , - (CO) OR ２２ -O-N=C(R ２３ ) ２ , -CR ２３ = N-OH, or -CR ２３ = N-O-R ２２ The terms "C1-C6 alkyl", "C2-C6 alkenyl", or "C2-C6 alkynyl" represent halogen, nitro, cyano, hydroxyl, mercapto, carboxyl, C3-C6 cycloalkyl, C3-C6 cycloalkenyl, heterocyclyl, aryl, -N(R) ２１ ) ２ ,-(CO)N(R ２１ ) ２ , -O(CO)N(R ２１ ) ２ , -O(CS)N(R ２１ ) ２ ,-(SO ２ )N(R ２１ ) ２ , -O(SO ２ )N(R ２１ ) ２ , -OR ２２ ,-(CO)R ２２ , -SR ２２ ,-(SO)R ２２ ,-(SO ２ ) R ２２ , -O(CO)H, -O(CO)R ２２ , -O-(SO ２ ) R ２２ , - (CO) OR ２２ , -O(CO)OR ２２ , -Si(R ２２ ) ３ , -O(CO)(CO)OH, -O(CO)(CO)OR ２２ -O-(C1-C6 alkylene)-(CO)OH, and -O-(C1-C6 alkylene)-(CO)OR ２２ It may be replaced by at least one group selected from; R ２１ Each of these is independently hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkenyl, aryl, heterocyclyl, -OR ２２ ,-(CO)R ２２ , - (CO) OR ２２ ,-(C1-C6 alkylene)-(CO)OR ２２ ,-(SO ２ ) R ２２ ,-(SO ２ ) OR ２２ , -(C1-C6 alkylene)-(SO ２ ) R ２２ ,-(CO)N(R ２４ ) ２ , or - (SO ２ )N(R ２４ ) ２ It represents; R ２２ Each of these independently represents a C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkenyl, aryl, or heterocyclyl, wherein the "C1-C6 alkyl," "C2-C6 alkenyl," or "C2-C6 alkynyl" can be a halogen, cyano, triC1-C6 alkylsilyl, C3-C6 cycloalkyl, C3-C6 cycloalkenyl, aryl, heterocyclyl, or -OR ２５ , -SR ２５ , -O(CO)R ２５ ,-(CO)R ２５ , - (CO) OR ２５ , and -O(CO)OR ２５ It may be replaced by at least one group selected from; R ２３ Each of these independently represents hydrogen, halogen, C1-C6 alkoxy, C1-C6 alkoxy, C1-C6 alkyl, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl, C1-C6 alkyl, C3-C6 cycloalkenyl, C3-C6 cycloalkenyl C1-C6 alkyl, aryl, aryl C1-C6 alkyl, heterocyclyl, or heterocyclyl C1-C6 alkyl; R ２４ Each independently represents hydrogen, 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 N(R) ２１ ) ２ and N(R ２４ ) ２ Each is independently either unsubstituted or substituted with at least one group selected from oxo, C1-C6 alkyl, and C1-C6 alkoxycarbonyl groups. 【Transformation 3】 R ２５ Each independently represents a phenyl substituted with at least one group selected from hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, halo-C1-C6 alkyl, halo-C2-C6 alkenyl, halo-C2-C6 alkynyl, phenyl, or the following: halogen, cyano, nitro, C1-C6 alkyl, halo-C1-C6 alkyl, C1-C6 alkoxy, halo-C1-C6 alkoxy, C1-C6 alkoxycarbonyl, C1-C6 alkylthio, C1-C6 alkylsulfonyl, phenoxy, and phenyl substituted with at least one group selected from halogen, cyano, nitro, C1-C6 alkyl, halo-C1-C6 alkyl, C1-C6 alkoxy, and halo-C1-C6 alkoxy; The above "C3-C6 cycloalkyl", "C3-C6 cycloalkenyl", "heterocyclyl", or "aryl" are 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 １０ , -SR １０ , - (CO) OR １０ ,-(SO ２ ) R １０ , -N(R １０ ) ２ and -O-(C1-C6 alkylene)-(CO)OR １０ It may be substituted with at least one group selected from -OCH, or two adjacent carbon atoms may be unsubstituted or substituted with a halogen. ２ CH ２ - or - OCH ２ It forms a fused ring with O-; R １０ This independently represents phenyl substituted with hydrogen, C1-C6 alkyl, halo-C1-C6 alkyl, phenyl, or 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; Preferably, the compound is selected from any one of the compounds in Table 1. A substituted pyrrolidone compound according to claim 1 or 2, characterized in that...

4. Substituted pyrrolidone compounds having the chiral center shown in formula I': 【Chemistry 4】 (In the formula, substituents Q, R ６ , R ７ , R ８ , W １ , W ２ The definitions of X, Y, and Z are as set forth in any one of claims 1 to 3; Preferably, based on the content of stereoisomers having R and S configurations at position 3, it has a stereochemical purity (S) of 60% to 100%, preferably 70% to 100%, more preferably 80% to 100%, even more preferably 90% to 100%, and even more preferably 95% to 100%; and based on the content of stereoisomers having R and S configurations at position 4, it has a stereochemical purity (S or R) of 60% to 100%, preferably 70% to 100%, more preferably 80% to 100%, even more preferably 90% to 100%, and even more preferably 95% to 100%; More preferably, the compound is selected from any one of the compounds in Table A.

5. A method for preparing a substituted pyrrolidone compound according to any one of claims 1 to 4, wherein the method comprises the following steps: A process to produce a compound represented by general formula I by reacting a compound represented by general formula II and a compound represented by general formula III. It includes, and the reaction equation is as follows: 【Transformation 5】 (In the formula, M represents OH or halogen, and substituents Q, R) ６ , R ７ , R ８ , W １ , W ２ The definitions of X, Y, and Z are as set forth in any one of claims 1 to 4; Preferably, the reaction is carried out with or without a coupling agent, in the presence of a base and a solvent, or without a base; more preferably, the base is selected from at least one of inorganic and organic bases; more preferably, the solvent is selected from at least one of DMF, DMA, methanol, ethanol, acetonitrile, dichloroethane, DMSO, dioxane, dichloromethane, and ethyl acetate; more preferably, the coupling agent is selected from at least one of Py-BOP, Py-AOP, EDCI, HOBT, DCC, HBTU, and HATU. The method described above is characterized in that it is as described above.

6. (i) comprising an herbicidally effective amount of at least one of the substituted pyrrolidone compounds described in any one of claims 1 to 4; preferably (ii) also comprising a formulation aid; more preferably (iii) further comprising an herbicidally effective amount of one or more additional herbicides and / or protective agents; The aforementioned additional herbicides are the following compounds: (1) VLCFA inhibitors: pretilachlor, butachlor, mefenacet, acetochlor, anirophos; (2) HPPD inhibitors: 【Transformation 6】 tefuryltrione, benzobicyclon, bipirazone; (3) PPO inhibitors: oxadiazone, pyraclonil, oxyfluorphen, oxaziargyl, pentoxazone, 【Transformation 7】 (4) Synthetic hormones: Harauxifen-methyl, Florpyrauxifen-benzyl 【Transformation 8】 , fluroxipil, 【Chemistry 9】 (5) PSII inhibitors: propanil, bentazon, simetrin; (6) DOXP inhibitors: Chromazon, 【Chemistry 10】 (7) PDS inhibitors: Bixlozone, 【Chemistry 11】 (8) FAT inhibitors: Symmethine, 【Chemistry 12】 (9) Other herbicides: Oxadiclomefone Selected from one or more of the following: The weight ratio of the active ingredient (i) in the composition to the additional herbicide in (iii) is 1:100 to 100:1, 1:80 to 80:1, 1:50 to 50:1, 1:30 to 30:1, 1:20 to 20:1, 1:10 to 10:1, 1:5 to 1:1, or 1:1 to 5:

1. A herbicide composition characterized in that respect.

7. A fungicidal composition characterized by comprising at least one of the substituted pyrrolidone compounds according to any one of claims 1 to 4 in a disease-inhibiting and botanically acceptable amount; preferably comprising a formulation aid; and more preferably further comprising another active ingredient.

8. An insecticide composition characterized by comprising a biologically effective amount of at least one of the substituted pyrrolidone compounds described in any one of claims 1 to 4; preferably comprising a formulation aid; and more preferably further comprising another active ingredient.

9. A method for controlling weeds, characterized in that it comprises applying an herbicidally effective amount of at least one of the substituted pyrrolidone compound according to any one of claims 1 to 4 or the herbicidal composition according to claim 6 to a plant or weed plot.

10. A method for preventing and controlling harmful fungi, comprising treating a material, plant, soil, or seed to be protected from the fungus or fungal parasitism with at least one of the substituted pyrrolidone compound according to any one of claims 1 to 4 or the fungicidal composition according to claim 7, in a disease-inhibiting and botanically acceptable amount.

11. A method for preventing and controlling pests, characterized in that it comprises exposing the pest or its environment to at least one of the substituted pyrrolidone compounds described in any one of claims 1 to 4 or the insecticidal composition described in claim 8 in a biologically effective amount.

12. The use of at least one of the substituted pyrrolidone compounds according to any one of claims 1 to 4 or the herbicidal composition according to claim 6 in the control of weeds; preferably, the substituted pyrrolidone compound is used to prevent or eliminate the weeds in a useful crop, and the useful crop is a transgenic crop or a crop treated by genome editing technology; or the use of at least one of the substituted pyrrolidone compounds according to any one of claims 1 to 4 or the fungicidal composition according to claim 7 in the prevention and control of plant pathogenic fungi; or the use of at least one of the substituted pyrrolidone compounds according to any one of claims 1 to 4 or the insecticidal composition according to claim 8 in the prevention and control of pests.

13. The intermediate represented by formula II or formula III as described in claim 5.

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