An arylcarboxamide compound containing a chiral sulfoxide or a salt thereof, a preparation method, a herbicidal composition, and an application

Abstract

This invention belongs to the field of pesticide technology, specifically relating to an aryl formamide compound containing a chiral sulfur oxide or its salt, its preparation method, herbicidal composition, and application. The aryl formamide compound containing a chiral sulfur oxide or its salt has the following structural formula: Z1 and Z2 independently represent nitro, halogen, cyano, etc.; X represents unsubstituted or substituted; Q represents halogen, cyano, cyanoalkyl, nitro, etc.; Y represents hydrogen, etc. The compound exhibits excellent herbicidal activity and higher crop safety, especially demonstrating good selectivity for key crops such as wheat, rice, and corn.

Description

Technical Field

[0001] This invention belongs to the field of pesticide technology, specifically relating to an arylformamide compound containing a chiral sulfur oxide or its salt, a preparation method, a herbicidal composition, and its application. Background Technology

[0002] Weed control is a crucial aspect of achieving efficient agriculture. Although a variety of herbicides are available on the market, such as WO2014086746A1, WO2016146561A1, WO2017144402A1, and WO2012028579A1, which disclose certain arylformamide compounds and their uses as herbicides, the market continues to expand. Issues such as weed resistance, herbicide lifespan, and cost-effectiveness, coupled with increasing environmental concerns, particularly the severe development of resistance to mainstream weed herbicides like penflusulfuron, bispyribac-sodium, nicosulfuron (ALS-inhibiting mechanisms), cyhalofop-butyl, clethodim, quizalofop-p-ethyl (ACCe-inhibiting mechanisms), and glyphosate, pose serious challenges to crops like wheat, corn, rice, cotton, and soybeans. The lack of effective herbicides for controlling resistant weeds necessitates continuous research and development by scientists to create new, efficient, safe, economical herbicides with different modes of action.

[0003] In addition, many chiral herbicides have been developed on the market, such as aryloxyphenoxypropionic acid herbicides quizalofop-P-ethyl, quizalofop-P-ethyl, cyhalofop-butyl, oxazolidinyl, and quizalofop-P-ethyl; aryloxypropionic acid herbicides 2,4-D propionic acid; and chloroamide herbicides S-metolachlor. The development of these chiral herbicides has significantly reduced the use of ineffective substances and provided greater protection for environmental safety. However, no sulfur-containing chiral herbicides have ever been commercialized. This application has also surprisingly discovered sulfur-containing chiral herbicides of aryl formamide compounds, which have great commercial value. Summary of the Invention

[0004] This invention provides an arylformamide compound containing a chiral sulfur oxide or its salt, a preparation method, a herbicidal composition, and an application. The compound exhibits excellent herbicidal activity and higher crop safety, especially demonstrating good selectivity for key crops such as wheat, rice, and corn.

[0005] The technical solution adopted in this invention is as follows:

[0006] An aryl formamide compound containing a chiral sulfur oxide or a salt thereof, with the following structural formula:

[0007]

[0008] Z1 and Z2 independently represent nitro, halogen, cyano, formyl, thiocyano, mercapto, alkyl, alkenyl, ynyl, cycloalkyl, cycloalkenyl, cycloalkylalkyl, or cycloalkenylalkyl, respectively, with or without halogen. 1 COR 1 COOR 1 OCOR 1 OCOOR 1 NR 3 SO2R 2 OSO2R 2 , S(O) m R 2 NR 3 COR 1 NR 3 COOR 1 C(O)NR 3 OR 1 SO2OR 1 C(O)NR 4 R 5 NR 3 C(O)NR 4 R 5 OC(O)NR 4 R 5 SO2NR 4 R 5 C(S)R 1 C(S)OR 1 C(S)SR 2 C(O)SR 2 SC(O)R 1 SC(S)R 1 OC(S)R 1 ,-alkyl-C(S)R 1 ,-alkyl-C(S)OR 1 ,-alkyl-C(O)SR 1 ,-alkyl-C(S)SR 1 ,-alkyl-SC(O)R 1 ,-alkyl-OC(S)R 1 ,-alkyl-SC(S)R 1 -O-alkyl-NR 4 R 5 ,-S-alkyl-NR 4 R 5 ,-alkyl-O-alkyl-NR 4 R 5 ,-alkyl-S-alkyl-NR 4 R 5 ,-alkyl-(C=S) n -NR4 R 5 ,-NH-alkyl-NR 4 R 5 ,-alkyl-OR 1 ,-alkyl-COR 1 ,-alkyl-CO2R 1 ,-alkyl-OCOR 1 ,-alkyl-NR 3 COR 1 ,-alkyl-SO2OR 1 ,-alkyl-NR 3 SO2R 2 ,-alkyl-OSO2R 2 ,-alkyl-S(O) m R 2 ,-alkyl-CONR 4 R 5 ,-alkyl-SO2NR 4 R 5 NR 4 R 5 , P(O)(OR 6 )2,CH2P(O)(OR 6 )2, -SO2NR 4 R 5 -alkyl-S(O) m R 2 ,-alkyl-CN, aryl, heteroaryl, heterocyclic, arylalkyl, heteroarylalkyl, heterocyclicalkyl;

[0009] R 1 R 3 R 4 R 5 Each of these groups independently represents hydrogen, aryl, arylalkyl, heteroaryl, heteroarylalkyl, alkyl, haloalkyl, alkenyl, haloalkenyl, ynyl, haloynyl, cycloalkyl, halocycloalkyl, alkoxyalkyl, and cycloalkylalkyl, wherein the last 10 groups are selected by s from cyano, halogen, nitro, cyanothio, OR 7 S(O) m R 9 NR 7 R 8 NR 8 OR 7 COR 7 OCOR 7 SCOR 7 NR 8 COR 7 CO2R 7 COSR 7 CONR 7R 8 Substitution of alkoxyalkoxycarbonyl groups;

[0010] R 2 Each of these groups independently represents aryl, arylalkyl, heteroaryl, heteroarylalkyl, alkyl, alkenyl, ynyl, cycloalkyl, and cycloalkylalkyl, wherein the last five groups are selected from cyano, halogen, nitro, cyanothio, OR 7 S(O) m R 9 NR 7 R 8 NR 8 OR 7 COR 7 OCOR 7 SCOR 7 NR 8 COR 7 CO2R 7 COSR 7 CONR 7 R 8 Substitution of alkoxy and alkoxycarbonyl groups;

[0011] R 6 Each can independently represent either methyl or ethyl;

[0012] R 7 R 8 Each can be independently represented as hydrogen, alkyl, alkenyl, or alkynyl;

[0013] R 9 Each can independently represent an alkyl, alkenyl, or alkynyl group;

[0014] X represents unsubstituted or substituted material.

[0015] R 11 Each of these independently represents hydrogen, halogen, cyano, nitro, unsubstituted or R-substituted. 13 Alkyl groups that are substituted in any way, unsubstituted or R 14 Arbitrarily substituted cycloalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, cycloalkenyl, NH2, aminoacyl, carboxyl, alkoxyalkoxycarbonyl, OR 15 ,-alkyl-OR 15 C(O)R 16 ,-alkyl-C(O)R 16 C(O)OR 16 ,-alkyl-C(O)OR 16 , S(O) m R 16 ,-alkyl-S(O) m R16 N(R) 16 )2,C(O)N(R 16 )2, NHC(O)R 17 Heterocyclic, heterocyclic alkyl, heterocyclic oxy, heterocyclic formyl, aryl, arylalkyl, aryloxy, arylformyl, heteroaryl, heteroarylalkyl, heteroaryloxy, heteroarylformyl;

[0016] R 12 Each of the following independently represents hydrogen, unsubstituted or replaced by R. 18 Alkyl, cycloalkyl, halocycloalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, cycloalkenyl, aryl;

[0017] Or when M is At that time, R 12 It can be done with R 11 Forming -(CH2)4- or -CH=CH-CH=CH- to react with R 12 The nitrogen atom and R that are combined 11 The carbon atoms that are bonded together form a 6-membered ring;

[0018] R 15 Each independently represents either unreplaced or replaced by R. 21 Alkyl, cycloalkyl, halocycloalkyl, alkenyl, haloalkenyl, ynyl, haloynyl, cycloalkenyl, or phenyl groups that are substituted in any way;

[0019] R 16 Each can independently represent alkyl, haloalkyl, cycloalkyl, alkenyl, haloalkenyl, ynyl, haloynyl, or cycloalkenyl;

[0020] R 21 Each of these independently represents halogen, cyano, cycloalkyl, hydroxyl, mercapto, alkoxy, and C(O)R. 22 Carboxyl, alkoxycarbonyl, alkoxyalkoxycarbonyl, -S(O) m -alkyl, heteroaryl, heterocyclic, unsubstituted or selected from R 23 A phenyl group substituted by at least one (e.g., 1, 2, 3, 4, or 5) group;

[0021] R 17 R 22 Each independently represents hydrogen, alkyl, or N(R) 24 )R 25 ;

[0022] R 23 Each of these independently represents a halogen, cyano, nitro, alkyl, unsubstituted, or R-substituted group. 31Arbitrarily substituted alkyl, cycloalkyl, halocycloalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, cycloalkenyl, alkylcarbonyl, cycloalkylcarbonyl, haloalkylcarbonyl, halocycloalkylcarbonyl, alkoxycarbonyl, haloalkoxycarbonyl, alkylaminocarbonyl, haloalkylaminocarbonyl, di(alkylamino)carbonyl, OR 32 , S(O) m R 33 , alkylaminosulfonyl, di(alkyl)aminosulfonyl, NH2, alkylamino, di(alkyl)amino, aryl, heteroaryl, heterocyclic;

[0023] R 24 and R 25 Each can independently represent hydrogen, alkyl, or phenyl, or R 24 It can be done with R 25 Together they form alkylene chains to react with R 24 and R 25 The nitrogen atoms that are bonded together form a 3- to 7-membered ring. At this time, the alkylene chain can contain one O, S, S(O), S(O)2, NH or N-alkyl, and can be substituted by an oxo group or a thio group.

[0024] R 13 R 14 R 18 R 31 Each of these independently represents halogen, cyano, nitro, carboxyl, alkoxycarbonyl, alkoxyalkoxycarbonyl, and S(O). m R 41 OR 42 Alkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, aryl, heteroaryl or heterocyclic;

[0025] R 32 Each can independently represent hydrogen, alkyl, haloalkyl, cycloalkyl, halocycloalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, or cycloalkenyl;

[0026] R 33 Each can independently represent alkyl, haloalkyl, cycloalkyl, alkenyl, haloalkenyl, ynyl, haloynyl, or cycloalkenyl;

[0027] R 41 R 42 Each can independently represent hydrogen, alkyl, haloalkyl, cycloalkyl, halocycloalkyl, alkenyl, haloalkenyl, ynyl, haloynyl, cycloalkenyl, phenyl, or benzyl.

[0028] Q represents halogen, cyano, cyanoalkyl, nitro, N(R) 51 )2,-alkyl-N(R 51 )2,-alkyl-N + (R51 )3, CON(R) 51 )2,-alkyl-CON(R 51 )2, Alkyl groups substituted with amino and carboxyl groups, OR 52 ,-alkyl-OR 52 COR 52 COOR 52 COSR 52 ,-alkyl-COR 52 ,-alkyl-COOR 52 ,-alkyl-COSR 52 ,-alkyl-OCOR 52 ,Si(R 52 )3,-alkyl-O-Si(R 52 )3,-alkyl-ON=C(R 52 )2, S(O) m R 53 ,-alkyl-S(O) m R 53 Alkyl, haloalkyl, unsubstituted or substituted alkenyl or ynyl groups selected from at least one (e.g., 1, 2, 3, 4, 5) of halogen, cyano, cycloalkyl, alkylcarbonyl, alkoxycarbonyl, alkoxy, alkylthio, alkylthionyl, alkylsulfonyl or trialkylsilyl, unsubstituted or substituted cycloalkyl or cycloalkylalkyl, unsubstituted or substituted heterocyclic, aryl, heteroaryl, heterocyclic alkyl, arylalkyl or heteroarylalkyl;

[0029] Y represents hydrogen, OR 54 SR 54 COR 54 OCOR 54 COOR 54 CON(R) 55 )2,N(R 55 )2, NR 56 COOR 54 NR 56 CON(R 55 )2,-alkyl-R 57 Alkyl, alkenyl, ynyl or cycloalkyl groups, whether or not they contain halogens, and unsubstituted or substituted arylalkyl or heteroarylalkyl groups;

[0030] R 57 Each independently represents an alkenyl, ynyl, or cycloalkyl group, with or without halogens; CN, OR 61 OCOR 61 COOR 61 COR 61 -O-(C=O)-OR 61 OSO2R 62SO2OR 61 , S(O) m R 62 N(R) 63 )2, CON(R) 63 )2, SO2N(R 63 )2, NR 64 COR 61 NR 64 SO2R 62 -O-(C=O)-N(R) 63 )2;

[0031] R 52 R 54 R 61 Each of these can independently represent hydrogen, and alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl or alkoxyalkyl groups, whether or not they contain halogens, as well as unsubstituted or substituted heterocyclic, heterocyclic alkyl, heterocyclic oxyalkyl, aryl, arylalkyl, aryloxyalkyl, heteroaryl, heteroarylalkyl or heteroaryloxyalkyl groups.

[0032] R 53 R 62 Each of these can independently represent alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl or alkoxyalkyl groups, whether they contain or do not contain halogens, as well as unsubstituted or substituted heterocyclic, heterocyclic alkyl, aryl, arylalkyl, heteroaryl or heteroarylalkyl groups;

[0033] R 51 R 55 R 56 R 63 R 64 Each of these independently represents hydrogen, nitro, alkoxyaminocarbonyl, trialkylsilyl, dialkylphosphonoyl, and N(R) 71 )2、CON(R 71 2. OR 71 COR 71 CO2R 71 COSR 71 OCOR 71 S(O) m R 72 Alkyl, halogenated alkyl, alkenyl, halogenated alkenyl, alkynyl, halogenated alkynyl, cycloalkyl, cycloalkenyl, halogenated cycloalkyl, alkoxyalkyl, cycloalkylalkyl, aryl, arylalkyl, aryloxyalkyl, arylalkyloxy, arylcarbonyl, arylsulfonyl, heteroaryl, heteroarylalkyl, heteroaryloxy, heteroaryloxyalkyl, heteroarylalkyloxy, heteroarylcarbonyl, heteroarylsulfonyl, heterocyclic, heterocyclic alkyl, heterocyclic oxy, heterocyclic oxyalkyl, heterocyclic alkyloxy, heterocyclic carbonyl, heterocyclic sulfonyl, -alkyl-NR21 -aryl, -alkyl-NR 21 -heteroaryl, -alkyl-NR 21 - Heterocyclic groups, wherein each of the last 35 groups mentioned is substituted with 0, 1, 2 or 3 groups selected from the following groups: cyano, halogen, nitro, cyanothio, OR 71 S(O) m R 72 、N(R 71 2. NR 71 OR 71 COR 71 OCOR 71 SCOR 72 NR 71 COR 71 NR 71 SO2R 72 CO2R 71 COSR 71 CON(R) 71 )2 and alkoxyalkoxycarbonyl;

[0034] R 71 Each can independently represent hydrogen, alkyl, alkenyl, ynyl, cycloalkyl, or cycloalkylalkyl;

[0035] R 72 Each can independently represent alkyl, alkenyl, ynyl, cycloalkyl, or cycloalkylalkyl;

[0036] r represents 0, 1, or 2;

[0037] m can represent 0, 1, or 2 independently;

[0038] n can represent 0 or 1 independently;

[0039] s can represent 0, 1, 2 or 3 independently.

[0040] Preferably, Z1 and Z2 independently represent nitro, halogen, cyano, formyl, thiocyano, mercapto, and C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkenyl, C3-C8 cycloalkylC1-C6 alkyl, or C3-C8 cycloalkenylC1-C6 alkyl, OR 1 COR 1 COOR 1 OCOR 1 OCOOR 1 NR 3 SO2R 2 OSO2R 2 , S(O) m R 2 NR3 COR 1 NR 3 COOR 1 C(O)NR 3 OR 1 SO2OR 1 C(O)NR 4 R 5 NR 3 C(O)NR 4 R 5 OC(O)NR 4 R 5 SO2NR 4 R 5 C(S)R 1 C(S)OR 1 C(S)SR 2 C(O)SR 2 SC(O)R 1 SC(S)R 1 OC(S)R 1 -(C1-C6)alkyl-C(S)R 1 -(C1-C6)alkyl-C(S)OR 1 ,-(C1-C6)alkyl-C(O)SR 1 ,-(C1-C6)alkyl-C(S)SR 1 ,-(C1-C6)alkyl-SC(O)R 1 ,-(C1-C6)alkyl-OC(S)R 1 -(C1-C6)alkyl-SC(S)R 1 -O-(C1-C6)alkyl-NR 4 R 5 -S-(C1-C6)alkyl-NR 4 R 5 -(C1-C6)alkyl-O-(C1-C6)alkyl-NR 4 R 5 -(C1-C6)alkyl-S-(C1-C6)alkyl-NR 4 R 5 ,-(C1-C6)alkyl-(C=S) n -NR 4 R 5 -NH-(C1-C6)alkyl-NR 4 R 5 ,-(C1-C6)alkyl-OR 1 ,-(C1-C6)alkyl-COR 1 ,-(C1-C6)alkyl-CO2R 1,-(C1-C6)alkyl-OCOR 1 ,-(C1-C6)alkyl-NR 3 COR 1 ,-(C1-C6)alkyl-SO2OR 1 ,-(C1-C6)alkyl-NR 3 SO2R 2 -(C1-C6)alkyl-OSO2R 2 ,-(C1-C6)alkyl-S(O) m R 2 ,-(C1-C6)alkyl-CONR 4 R 5 ,-(C1-C6)alkyl-SO2NR 4 R 5 NR 4 R 5 , P(O)(OR 6 )2,CH2P(O)(OR 6 )2, -SO2NR 4 R 5 -(C1-C6)alkyl-S(O) m R 2 -(C1-C6)alkyl-CN, aryl, heteroaryl, heterocyclic, arylC1-C6alkyl, heteroarylC1-C6alkyl, heterocyclicC1-C6alkyl;

[0041] R 1 R 3 R 4 R 5 Each of these groups independently represents hydrogen, aryl, aryl C1-C6 alkyl, heteroaryl, heteroaryl C1-C6 alkyl, C1-C8 alkyl, halogenated C1-C8 alkyl, C2-C8 alkenyl, halogenated C2-C8 alkenyl, C2-C8 ynyl, halogenated C2-C8 ynyl, C3-C8 cycloalkyl, halogenated C3-C8 cycloalkyl, C1-C8 alkoxy-C1-C6 alkyl, and C3-C8 cycloalkyl-C1-C6 alkyl, wherein the last 10 groups are selected from cyano, halogen, nitro, cyanothio, OR 7 S(O) m R 9 NR 7 R 8 NR 8 OR 7 COR 7 OCOR 7 SCOR 7 NR 8 COR 7 CO2R 7COSR 7 CONR 7 R 8 Substitution with C1-C8 alkoxy and C1-C6 alkoxy carbonyl groups;

[0042] R 2 Each of these groups independently represents aryl, aryl C1-C6 alkyl, heteroaryl, heteroaryl C1-C6 alkyl, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 ynyl, C3-C8 cycloalkyl, and C3-C8 cycloalkyl C1-C6 alkyl, wherein the last five groups are selected from cyano, halogen, nitro, cyanothio, OR 7 S(O) m R 9 NR 7 R 8 NR 8 OR 7 COR 7 OCOR 7 SCOR 7 NR 8 COR 7 CO2R 7 COSR 7 CONR 7 R 8 Substitution of C1-C8 alkoxy and C1-C6 alkoxy carbonyl groups;

[0043] R 6 Each can independently represent either methyl or ethyl;

[0044] R 7 R 8 Each can be independently represented as hydrogen, C1-C8 alkyl, C2-C8 alkenyl, or C2-C8 alkynyl;

[0045] R 9 Each can independently represent a C1-C8 alkyl, a C2-C8 alkenyl, or a C2-C8 alkynyl group;

[0046] X represents unsubstituted or substituted material.

[0047] R 11 Each of these independently represents hydrogen, halogen, cyano, nitro, unsubstituted or R-substituted. 13 Arbitrarily substituted C1-C8 alkyl groups, unsubstituted or R 14 Arbitrarily substituted C3-C8 cycloalkyl, C2-C8 alkenyl, halogenated C2-C8 alkenyl, C2-C8 alkynyl, halogenated C2-C8 alkynyl, C3-C8 cycloalkenyl, NH2, aminoacyl, carboxyl, C1-C8 alkoxy, C1-C6 alkoxycarbonyl, OR 15,-(C1-C6)alkyl-OR 15 C(O)R 16 -(C1-C6)alkyl-C(O)R 16 C(O)OR 16 -(C1-C6)alkyl-C(O)OR 16 , S(O) m R 16 ,-(C1-C6)alkyl-S(O) m R 16 N(R) 16 )2,C(O)N(R 16 )2, NHC(O)R 17 Heterocyclic, heterocyclic C1-C6 alkyl, heterocyclic oxy, heterocyclic formyl, aryl, aryl C1-C6 alkyl, aryloxy, arylformyl, heteroaryl, heteroaryl C1-C6 alkyl, heteroaryloxy, heteroarylformyl;

[0048] R 12 Each of the following independently represents hydrogen, unsubstituted or replaced by R. 18 Arbitrarily substituted C1-C8 alkyl, C3-C8 cycloalkyl, halo-C3-C8 cycloalkyl, C2-C8 alkenyl, halo-C2-C8 alkenyl, C2-C8 ynyl, halo-C2-C8 ynyl, C3-C8 cycloalkenyl, aryl;

[0049] Or when M is At that time, R 12 It can be done with R 11 Forming -(CH2)4- or -CH=CH-CH=CH- to react with R 12 The nitrogen atom and R that are combined 11 The carbon atoms that are bonded together form a 6-membered ring;

[0050] R 15 Each independently represents either unreplaced or replaced by R. 21 The C1-C8 alkyl, C3-C8 cycloalkyl, halo-C3-C8 cycloalkyl, C2-C8 alkenyl, halo-C2-C8 alkenyl, C2-C8 ynyl, halo-C2-C8 ynyl, C3-C8 cycloalkenyl or phenyl groups are substituted in any way.

[0051] R 16 Each of these can independently represent C1-C8 alkyl, halo-C1-C8 alkyl, C3-C8 cycloalkyl, C2-C8 alkenyl, halo-C2-C8 alkenyl, C2-C8 alkynyl, halo-C2-C8 alkynyl, or C3-C8 cycloalkenyl.

[0052] R 21 Each of these groups independently represents a halogen, cyano group, C3-C8 cycloalkyl group, hydroxyl group, mercapto group, C1-C8 alkoxy group, or -C(O)R group.22 Carboxyl, C1-C8 alkoxycarbonyl, C1-C8 alkoxy-C1-C6 alkoxycarbonyl, -S(O) m -(C1-C8)alkyl, heteroaryl, heterocyclic, unsubstituted or selected from R 23 A phenyl group substituted by at least one (e.g., 1, 2, 3, 4, or 5) group;

[0053] R 17 R 22 Each can independently represent hydrogen, C1-C8 alkyl, or N(R) 24 )R 25 ;

[0054] R 23 Each of these independently represents a halogen, cyano, nitro, C1-C8 alkyl, unsubstituted or R-substituted group. 31 Arbitrarily substituted C1-C8 alkyl, C3-C8 cycloalkyl, halo-C3-C8 cycloalkyl, C2-C8 alkenyl, halo-C2-C8 alkenyl, C2-C8 ynyl, halo-C2-C8 ynyl, C3-C8 cycloalkenyl, C1-C8 alkyl carbonyl, C3-C8 cycloalkyl carbonyl, halo-C1-C8 alkyl carbonyl, halo-C3-C8 cycloalkyl carbonyl, C1-C8 alkoxy carbonyl, halo-C1-C8 alkoxy carbonyl, C1-C8 alkylamino carbonyl, halo-C1-C8 alkylamino carbonyl, di(C1-C8 alkylamino)carbonyl, OR 32 , S(O) m R 33 C1-C8 alkylaminosulfonyl, di(C1-C8 alkyl)aminosulfonyl, NH2, C1-C8 alkylamino, di(C1-C8 alkyl)amino, aryl, heteroaryl, heterocyclic;

[0055] R 24 and R 25 Each can independently represent hydrogen, C1-C8 alkyl or phenyl, or R 24 It can be done with R 25 Together they form C2-C8 alkylene chains to react with R 24 and R 25 The nitrogen atoms that are bonded together form a 3- to 7-membered ring. At this time, the alkylene chain can contain one O, S, S(O), S(O)2, NH or N-alkyl, and can be substituted by an oxo group or a thio group.

[0056] R 13 R 14 R 18 R 31 Each of these groups independently represents halogen, cyano, nitro, carboxyl, C1-C8 alkoxycarbonyl, C1-C8 alkoxyC1-C6 alkoxycarbonyl, and S(O). m R41 OR 42 C1-C8 alkyl, halo-C1-C8 alkyl, C2-C8 alkenyl, halo-C2-C8 alkenyl, C2-C8 alkynyl, halo-C2-C8 alkynyl, aryl, heteroaryl or heterocyclic;

[0057] R 32 Each of these can independently represent hydrogen, C1-C8 alkyl, halo-C1-C8 alkyl, C3-C8 cycloalkyl, halo-C3-C8 cycloalkyl, C2-C8 alkenyl, halo-C2-C8 alkenyl, C2-C8 alkynyl, halo-C2-C8 alkynyl, or C3-C8 cycloalkenyl.

[0058] R 33 Each of these can independently represent C1-C8 alkyl, halo-C1-C8 alkyl, C3-C8 cycloalkyl, C2-C8 alkenyl, halo-C2-C8 alkenyl, C2-C8 alkynyl, halo-C2-C8 alkynyl, or C3-C8 cycloalkenyl.

[0059] R 41 R 42 Each of these can independently represent hydrogen, C1-C8 alkyl, halo-C1-C8 alkyl, C3-C8 cycloalkyl, halo-C3-C8 cycloalkyl, C2-C8 alkenyl, halo-C2-C8 alkenyl, C2-C8 ynyl, halo-C2-C8 ynyl, C3-C8 cycloalkenyl, phenyl, or benzyl.

[0060] Q represents halogen, cyano, cyano C1-C6 alkyl, nitro, N(R) 51 )2,-(C1-C6)alkyl-N(R 51 )2,-(C1-C6)alkyl-N + (R 51 )3, CON(R) 51 )2,-(C1-C6)alkyl-CON(R 51 )2, C1-C6 alkyl groups substituted with amino and carboxyl groups, OR 52 ,-(C1-C6)alkyl-OR 52 COR 52 COOR 52 COSR 52 ,-(C1-C6)alkyl-COR 52 ,-(C1-C6)alkyl-COOR 52 ,-(C1-C6)alkyl-COSR 52 ,-(C1-C6)alkyl-OCOR 52 ,Si(R 52 )3,-(C1-C6)alkyl-O-Si(R 52 )3,-(C1-C6)alkyl-ON=C(R 52)2, S(O) m R 53 ,-(C1-C6)alkyl-S(O) m R 53 C1-C8 alkyl, halogenated C1-C8 alkyl, unsubstituted or substituted C2-C8 alkenyl or C2-C8 alkynyl or substituted C2-C8 alkylthioyl, C1-C8 alkylthionyl, C1-C8 alkylsulfonyl or triC1-C8 alkylsilyl, unsubstituted or substituted C3-C8 cycloalkyl or C3-C8 cycloalkylC1-C6 alkyl, unsubstituted or substituted heterocyclic, aryl, heteroaryl, heterocyclic C1-C6 alkyl, aryl C1-C6 alkyl or heteroaryl C1-C6 alkyl;

[0061] Y represents hydrogen, OR 54 SR 54 COR 54 OCOR 54 COOR 54 CON(R) 55 )2,N(R 55 )2, NR 56 COOR 54 NR 56 CON(R 55 )2,-(C1-C6)alkyl-R 57 C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl or C3-C8 cycloalkyl, with or without halogens, and unsubstituted or substituted aryl C1-C6 alkyl or heteroaryl C1-C6 alkyl;

[0062] R 57 Each independently represents a C2-C8 alkenyl, C2-C8 ynyl, or C3-C8 cycloalkyl group, with or without halogens, CN, OR 61 OCOR 61 COOR 61 COR 61 -O-(C=O)-OR 61 OSO2R 62 SO2OR 61 , S(O) m R 62 N(R) 63 )2, CON(R) 63 )2, SO2N(R 63 )2, NR 64 COR61 NR 64 SO2R 62 -O-(C=O)-N(R) 63 )2;

[0063] R 52 R 54 R 61 Each of these groups independently represents hydrogen, and includes C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C1-C8 alkyl, C3-C8 cycloalkyl C1-C6 alkyl, C3-C8 cycloalkenyl or C1-C8 alkoxy C1-C6 alkyl groups, as well as unsubstituted or substituted heterocyclic groups, heterocyclic C1-C6 alkyl, heterocyclic oxy C1-C6 alkyl, aryl, aryl C1-C6 alkyl, aryloxy C1-C6 alkyl, heteroaryl, heteroaryl C1-C6 alkyl or heteroaryloxy C1-C6 alkyl groups;

[0064] R 53 R 62 Each of these groups independently represents C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkylC1-C6 alkyl, C3-C8 cycloalkenyl or C1-C8 alkoxyC1-C6 alkyl groups, and unsubstituted or substituted heterocyclic groups, heterocyclic C1-C6 alkyl groups, aryl, aryl C1-C6 alkyl groups, heteroaryl or heteroaryl C1-C6 alkyl groups;

[0065] R 51 R 55 R 56 R 63 R 64 Each of these independently represents hydrogen, nitro, C1-C8 alkoxyaminocarbonyl, triC1-C8 alkylsilyl, diC1-C8 alkylphosphonoyl, and N(R) 71 )2、CON(R 71 2. OR 71 COR 71 CO2R 71 COSR 71 OCOR 71 S(O) m R 72C1-C8 alkyl, halogenated C1-C8 alkyl, C2-C8 alkenyl, halogenated C2-C8 alkenyl, C2-C8 alkynyl, halogenated C2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkenyl, halogenated C3-C8 cycloalkyl, C1-C8 alkoxy-C1-C6 alkyl, C3-C8 cycloalkyl-C1-C6 alkyl, aryl, aryl C1-C6 alkyl, aryloxy, aryloxy-C1-C6 alkyl, aryl C1- C6 alkyloxy, arylcarbonyl, arylsulfonyl, heteroaryl, heteroaryl C1-C6 alkyl, heteroaryloxy, heteroaryloxy C1-C6 alkyl, heteroaryl C1-C6 alkyloxy, heteroaryl carbonyl, heteroarylsulfonyl, heterocyclic, heterocyclic C1-C6 alkyl, heterocyclic oxygen, heterocyclic oxygen C1-C6 alkyl, heterocyclic C1-C6 alkyloxy, heterocyclic carbonyl, heterocyclic sulfonyl, -(C1-C6)alkyl-NR 21 -aryl, -(C1-C6)alkyl-NR 21 -heteroaryl, -(C1-C6)alkyl-NR 21 - Heterocyclic groups, wherein each of the last 35 groups mentioned is substituted with 0, 1, 2 or 3 groups selected from the following groups: cyano, halogen, nitro, cyanothio, OR 71 S(O) m R 72 、N(R 71 2. NR 71 OR 71 COR 71 OCOR 71 SCOR 72 NR 71 COR 71 NR 71 SO2R 72 CO2R 71 COSR 71 CON(R) 71 )2 and C1-C8 alkoxy and C1-C6 alkoxy carbonyl;

[0066] R 71 Each of these can independently represent hydrogen, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, or C3-C8 cycloalkyl / C1-C6 alkyl.

[0067] R 72 Each of these can independently represent C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, or C3-C8 cycloalkyl-C1-C6 alkyl.

[0068] r represents 0, 1, or 2;

[0069] m can represent 0, 1, or 2 independently;

[0070] n can represent 0 or 1 independently;

[0071] s can represent 0, 1, 2 or 3 independently.

[0072] More preferably, Z1 and Z2 independently represent nitro, halogen, cyano, formyl, thiocyano, mercapto, and C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkenyl, C3-C6 cycloalkylC1-C3 alkyl, or C3-C6 cycloalkenylC1-C3 alkyl, OR 1 COR 1 COOR 1 OCOR 1 OCOOR 1 NR 3 SO2R 2 OSO2R 2 , S(O) m R 2 NR 3 COR 1 NR 3 COOR 1 C(O)NR 3 OR 1 SO2OR 1 C(O)NR 4 R 5 NR 3 C(O)NR 4 R 5 OC(O)NR 4 R 5 SO2NR 4 R 5 C(S)R 1 C(S)OR 1 C(S)SR 2 C(O)SR 2 SC(O)R 1 SC(S)R 1 OC(S)R 1 ,-(C1-C3)alkyl-C(S)R 1 ,-(C1-C3)alkyl-C(S)OR 1 ,-(C1-C3)alkyl-C(O)SR 1 ,-(C1-C3)alkyl-C(S)SR 1 ,-(C1-C3)alkyl-SC(O)R 1 ,-(C1-C3)alkyl-OC(S)R 1 ,-(C1-C3)alkyl-SC(S)R1 -O-(C1-C3)alkyl-NR 4 R 5 -S-(C1-C3)alkyl-NR 4 R 5 -(C1-C3)alkyl-O-(C1-C3)alkyl-NR 4 R 5 -(C1-C3)alkyl-S-(C1-C3)alkyl-NR 4 R 5 ,-(C1-C3)alkyl-(C=S) n -NR 4 R 5 -NH-(C1-C3)alkyl-NR 4 R 5 ,-(C1-C3)alkyl-OR 1 ,-(C1-C3)alkyl-COR 1 ,-(C1-C3)alkyl-CO2R 1 ,-(C1-C3)alkyl-OCOR 1 ,-(C1-C3)alkyl-NR 3 COR 1 ,-(C1-C3)alkyl-SO2OR 1 ,-(C1-C3)alkyl-NR 3 SO2R 2 -(C1-C3)alkyl-OSO2R 2 ,-(C1-C3)alkyl-S(O) m R 2 ,-(C1-C3)alkyl-CONR 4 R 5 ,-(C1-C3)alkyl-SO2NR 4 R 5 NR 4 R 5 , P(O)(OR 6 )2,CH2P(O)(OR 6 )2, -SO2NR 4 R 5 -(C1-C3)alkyl-S(O) m R 2 -(C1-C3)alkyl-CN, aryl, heteroaryl, heterocyclic, arylC1-C3alkyl, heteroarylC1-C3alkyl, heterocyclicC1-C3alkyl;

[0073] R 1 R 3 R 4 R5 Each of these groups independently represents hydrogen, aryl, aryl C1-C3 alkyl, heteroaryl, heteroaryl C1-C3 alkyl, C1-C6 alkyl, halogenated C1-C6 alkyl, C2-C6 alkenyl, halogenated C2-C6 alkenyl, C2-C6 ynyl, halogenated C2-C6 ynyl, C3-C6 cycloalkyl, halogenated C3-C6 cycloalkyl, C1-C6 alkoxy C1-C3 alkyl, and C3-C6 cycloalkyl C1-C3 alkyl, wherein the last 10 groups are selected from cyano, halogen, nitro, cyanothio, OR 7 S(O) m R 9 NR 7 R 8 NR 8 OR 7 COR 7 OCOR 7 SCOR 7 NR 8 COR 7 CO2R 7 COSR 7 CONR 7 R 8 Substitution with C1-C6 alkoxy and C1-C3 alkoxy carbonyl groups;

[0074] R 2 Each of these groups independently represents aryl, aryl C1-C3 alkyl, heteroaryl, heteroaryl C1-C3 alkyl, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 ynyl, C3-C6 cycloalkyl, and C3-C6 cycloalkyl C1-C3 alkyl, wherein the last five groups are selected from cyano, halogen, nitro, cyanothio, OR 7 S(O) m R 9 NR 7 R 8 NR 8 OR 7 COR 7 OCOR 7 SCOR 7 NR 8 COR 7 CO2R 7 COSR 7 CONR 7 R 8 Substitution of C1-C6 alkoxy and C1-C3 alkoxy carbonyl groups;

[0075] R 6 Each can independently represent either methyl or ethyl;

[0076] R 7 R8 Each can be independently represented as hydrogen, C1-C6 alkyl, C2-C6 alkenyl, or C2-C6 alkynyl;

[0077] R 9 Each can independently represent a C1-C6 alkyl, a C2-C6 alkenyl, or a C2-C6 alkynyl group;

[0078] X represents unsubstituted or substituted material.

[0079] R 11 Each of these independently represents hydrogen, halogen, cyano, nitro, unsubstituted or R-substituted. 13 Arbitrarily substituted C1-C6 alkyl groups, unsubstituted or R 14 Arbitrarily substituted C3-C6 cycloalkyl, C2-C6 alkenyl, halogenated C2-C6 alkenyl, C2-C6 alkynyl, halogenated C2-C6 alkynyl, C3-C6 cycloalkenyl, NH2, aminoacyl, carboxyl, C1-C6 alkoxy, C1-C3 alkoxy carbonyl, OR 15 ,-(C1-C3)alkyl-OR 15 C(O)R 16 ,-(C1-C3)alkyl-C(O)R 16 C(O)OR 16 ,-(C1-C3)alkyl-C(O)OR 16 , S(O) m R 16 ,-(C1-C3)alkyl-S(O) m R 16 N(R) 16 )2,C(O)N(R 16 )2, NHC(O)R 17 Heterocyclic, heterocyclic C1-C3 alkyl, heterocyclic oxy, heterocyclic formyl, aryl, aryl C1-C3 alkyl, aryloxy, arylformyl, heteroaryl, heteroaryl C1-C3 alkyl, heteroaryloxy, heteroarylformyl;

[0080] R 12 Each of the following independently represents hydrogen, unsubstituted or replaced by R. 18 Arbitrarily substituted C1-C6 alkyl, C3-C6 cycloalkyl, halo-C3-C6 cycloalkyl, C2-C6 alkenyl, halo-C2-C6 alkenyl, C2-C6 ynyl, halo-C2-C6 ynyl, C3-C6 cycloalkenyl, aryl;

[0081] Or when M is At that time, R 12 It can be done with R 11 Forming -(CH2)4- or -CH=CH-CH=CH- to react with R12 The nitrogen atom and R that are combined 11 The carbon atoms that are bonded together form a 6-membered ring;

[0082] R 15 Each independently represents either unreplaced or replaced by R. 21 The C1-C6 alkyl, C3-C6 cycloalkyl, halo-C3-C6 cycloalkyl, C2-C6 alkenyl, halo-C2-C6 alkenyl, C2-C6 ynyl, halo-C2-C6 ynyl, C3-C6 cycloalkenyl or phenyl groups are substituted in any way.

[0083] R 16 Each of these can independently represent C1-C6 alkyl, halo-C1-C6 alkyl, C3-C6 cycloalkyl, C2-C6 alkenyl, halo-C2-C6 alkenyl, C2-C6 alkynyl, halo-C2-C6 alkynyl, or C3-C6 cycloalkenyl.

[0084] R 21 Each of these groups independently represents a halogen, cyano group, C3-C6 cycloalkyl group, hydroxyl group, mercapto group, C1-C6 alkoxy group, and -C(O)R group. 22 Carboxyl, C1-C6 alkoxycarbonyl, C1-C6 alkoxy-C1-C3 alkoxycarbonyl, -S(O) m -(C1-C6)alkyl, heteroaryl, heterocyclic, unsubstituted or selected from R 23 A phenyl group substituted by at least one (e.g., 1, 2, 3, 4, or 5) group;

[0085] R 17 R 22 Each can independently represent hydrogen, C1-C6 alkyl, or N(R) 24 )R 25 ;

[0086] R 23 Each of these independently represents a halogen, cyano, nitro, C1-C6 alkyl, unsubstituted or R-substituted group. 31 Arbitrarily substituted C1-C6 alkyl, C3-C6 cycloalkyl, halo-C3-C6 cycloalkyl, C2-C6 alkenyl, halo-C2-C6 alkenyl, C2-C6 ynyl, halo-C2-C6 ynyl, C3-C6 cycloalkenyl, C1-C6 alkyl carbonyl, C3-C6 cycloalkyl carbonyl, halo-C1-C6 alkyl carbonyl, halo-C3-C6 cycloalkyl carbonyl, C1-C6 alkoxy carbonyl, halo-C1-C6 alkoxy carbonyl, C1-C6 alkylamino carbonyl, halo-C1-C6 alkylamino carbonyl, di(C1-C6 alkylamino)carbonyl, OR 32 , S(O) m R 33C1-C6 alkylaminosulfonyl, di(C1-C6 alkyl)aminosulfonyl, NH2, C1-C6 alkylamino, di(C1-C6 alkyl)amino, aryl, heteroaryl, heterocyclic

[0087] R 24 and R 25 Each can independently represent hydrogen, C1-C6 alkyl or phenyl, or R 24 It can be done with R 25 Together they form a C2-C6 alkylene chain to react with R 24 and R 25 The nitrogen atoms that are bonded together form a 3- to 7-membered ring. At this time, the alkylene chain can contain one O, S, S(O), S(O)2, NH or N-alkyl, and can be substituted by an oxo group or a thio group.

[0088] R 13 R 14 R 18 R 31 Each of these groups independently represents halogen, cyano, nitro, carboxyl, C1-C6 alkoxycarbonyl, C1-C6 alkoxyC1-C3 alkoxycarbonyl, and S(O). m R 41 OR 42 C1-C6 alkyl, halo-C1-C6 alkyl, C2-C6 alkenyl, halo-C2-C6 alkenyl, C2-C6 alkynyl, halo-C2-C6 alkynyl, aryl, heteroaryl or heterocyclic;

[0089] R 32 Each of these can independently represent hydrogen, C1-C6 alkyl, halo-C1-C6 alkyl, C3-C6 cycloalkyl, halo-C3-C6 cycloalkyl, C2-C6 alkenyl, halo-C2-C6 alkenyl, C2-C6 ynyl, halo-C2-C6 ynyl, or C3-C6 cycloalkenyl.

[0090] R 33 Each of these can independently represent C1-C6 alkyl, halo-C1-C6 alkyl, C3-C6 cycloalkyl, C2-C6 alkenyl, halo-C2-C6 alkenyl, C2-C6 alkynyl, halo-C2-C6 alkynyl, or C3-C6 cycloalkenyl.

[0091] R 41 R 42 Each of these can independently represent hydrogen, C1-C6 alkyl, halo-C1-C6 alkyl, C3-C6 cycloalkyl, halo-C3-C6 cycloalkyl, C2-C6 alkenyl, halo-C2-C6 alkenyl, C2-C6 ynyl, halo-C2-C6 ynyl, C3-C6 cycloalkenyl, phenyl, or benzyl.

[0092] Q represents halogen, cyano, cyano C1-C3 alkyl, nitro, N(R) 51)2,-(C1-C3)alkyl-N(R 51 )2,-(C1-C3)alkyl-N + (R 51 )3, CON(R) 51 )2,-(C1-C3)alkyl-CON(R 51 )2, C1-C3 alkyl groups substituted with amino and carboxyl groups, OR 52 ,-(C1-C3)alkyl-OR 52 COR 52 COOR 52 COSR 52 ,-(C1-C3)alkyl-COR 52 ,-(C1-C3)alkyl-COOR 52 ,-(C1-C3)alkyl-COSR 52 ,-(C1-C3)alkyl-OCOR 52 ,Si(R 52 )3,-(C1-C3)alkyl-O-Si(R 52 )3,-(C1-C3)alkyl-ON=C(R 52 )2, S(O) m R 53 ,-(C1-C3)alkyl-S(O) m R 53 C1-C8 alkyl, halogenated C1-C6 alkyl, unsubstituted or substituted C2-C6 alkenyl or C2-C6 alkynyl or substituted C2-C6 alkenyl or alkylthioyl or alkylthionyl or alkylsulfonyl or triC1-C6 alkylsilyl or alkylthioyl or alkylthion ...

[0093] Y represents hydrogen, OR 54 SR 54 COR 54 OCOR 54 COOR 54 CON(R) 55 )2,N(R 55 )2, NR 56 COOR 54 NR 56 CON(R55 )2,-(C1-C3)alkyl-R 57 C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl or C3-C6 cycloalkyl, with or without halogens, and unsubstituted or substituted aryl C1-C3 alkyl or heteroaryl C1-C3 alkyl;

[0094] R 57 Each of these independently represents a C2-C6 alkenyl, C2-C6 ynyl, or C3-C6 cycloalkyl group, with or without halogens; CN, OR 61 OCOR 61 COOR 61 COR 61 -O-(C=O)-OR 61 OSO2R 62 SO2OR 61 , S(O) m R 62 N(R) 63 )2, CON(R) 63 )2, SO2N(R 63 )2, NR 64 COR 61 NR 64 SO2R 62 -O-(C=O)-N(R) 63 )2;

[0095] R 52 R 54 R 61 Each of these groups independently represents hydrogen, and includes C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 alkyl, C3-C6 cycloalkyl C1-C3 alkyl, C3-C6 cycloalkenyl or C1-C6 alkoxy C1-C3 alkyl groups, as well as unsubstituted or substituted heterocyclic groups, heterocyclic C1-C3 alkyl, heterocyclic oxy C1-C3 alkyl, aryl, aryl C1-C3 alkyl, aryloxy C1-C3 alkyl, heteroaryl, heteroaryl C1-C3 alkyl or heteroaryloxy C1-C3 alkyl groups;

[0096] R 53 R 62 Each of these can independently represent C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C3 alkyl, C3-C6 cycloalkenyl or C1-C6 alkoxy C1-C3 alkyl, and unsubstituted or substituted heterocyclic, heterocyclic C1-C3 alkyl, aryl, aryl C1-C3 alkyl, heteroaryl or heteroaryl C1-C3 alkyl;

[0097] R 51R 55 R 56 R 63 R 64 Each of these independently represents hydrogen, nitro, C1-C6 alkoxyaminocarbonyl, triC1-C6 alkylsilyl, diC1-C6 alkylphosphonoyl, and N(R) 71 )2、CON(R 71 2. OR 71 COR 71 CO2R 71 COSR 71 OCOR 71 S(O) m R 72 C1-C6 alkyl, halogenated C1-C6 alkyl, C2-C6 alkenyl, halogenated C2-C6 alkenyl, C2-C6 alkynyl, halogenated C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkenyl, halogenated C3-C6 cycloalkyl, C1-C6 alkoxy-C1-C3 alkyl, C3-C6 cycloalkyl-C1-C3 alkyl, aryl, aryl C1-C3 alkyl, aryloxy, aryloxy-C1-C3 alkyl, aryl C1- C3 alkyloxy, aryl carbonyl, aryl sulfonyl, heteroaryl, heteroaryl C1-C3 alkyl, heteroaryloxy, heteroaryloxy C1-C3 alkyl, heteroaryl C1-C3 alkyloxy, heteroaryl carbonyl, heteroaryl sulfonyl, heterocyclic, heterocyclic C1-C3 alkyl, heterocyclic oxygen, heterocyclic oxygen C1-C3 alkyl, heterocyclic C1-C3 alkyloxy, heterocyclic carbonyl, heterocyclic sulfonyl, -(C1-C3)alkyl-NR 21 -aryl, -(C1-C3)alkyl-NR 21 -heteroaryl, -(C1-C3)alkyl-NR 21 - Heterocyclic groups, wherein each of the last 35 groups mentioned is substituted with 0, 1, 2 or 3 groups selected from the following groups: cyano, halogen, nitro, cyanothio, OR 71 S(O) m R 72 、N(R 71 2. NR 71 OR 71 COR 71 OCOR 71 SCOR 72 NR 71 COR 71 NR 71 SO2R 72 CO2R 71 COSR 71 CON(R) 71 )2 and C1-C6 alkoxy and C1-C3 alkoxy carbonyl;

[0098] R 71 Each of these can independently represent hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, or C3-C6 cycloalkyl / C1-C3 alkyl;

[0099] R 72 Each of these can independently represent C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, or C3-C6 cycloalkyl / C1-C3 alkyl.

[0100] r represents 0, 1, or 2;

[0101] m can represent 0, 1, or 2 independently;

[0102] n can represent 0 or 1 independently;

[0103] s can represent 0, 1, 2 or 3 independently.

[0104] More preferably, Z1 represents halogen (such as fluorine, chlorine), cyano, C1-C6 alkyl (such as methyl), C1-C6 alkoxy (such as methoxy), C1-C6 alkoxy-C1-C6 alkoxy, C1-C6 alkoxy-C1-C6 alkylthio or C1-C6 alkylthio (such as methylthio).

[0105] Z2 represents halogen, C1-C6 alkyl, halogenated C1-C6 alkyl (such as trifluoromethyl, difluoromethyl) or C1-C6 alkyl sulfonyl (such as methylsulfonyl);

[0106] X represents each independently

[0107] R 11 Each can independently represent hydrogen, C1-C6 alkyl, or C3-C6 cycloalkyl;

[0108] R 12 Each can independently represent hydrogen, C1-C6 alkyl, or C1-C6 alkoxy-C1-C3 alkyl;

[0109] Q represents cyano, cyano C1-C3 alkyl, and -(C1-C3)alkyl-N(R) independently. 51 )2, CON(R) 51 )2,-(C1-C3)alkyl-CON(R 51 )2,-(C1-C3)alkyl-OR 52 COR 52 ,-(C1-C3)alkyl-COR 52 ,-(C1-C3)alkyl-COOR 52 ,-(C1-C3)alkyl-COSR 52,-(C1-C3)alkyl-OCOR 52 ,Si(R 52 )3,-(C1-C3)alkyl-O-Si(R 52 )3,-(C1-C3)alkyl-ON=C(R 52 2,-(C1-C3)alkyl-S(O) m -(C1-C6)alkyl, C1-C8alkyl, halo-C1-C6alkyl, C2-C6alkenyl, C2-C6ynyl, halo-C2-C6alkenyl, C3-C6cycloalkyl-C1-C3alkyl, unsubstituted or substituted heterocyclic, heterocyclic C1-C3alkyl, heteroaryl C1-C3alkyl or phenyl C1-C3alkyl;

[0110] R 51 Each can independently represent hydrogen or C1-C6 alkyl groups;

[0111] R 52 Each can independently represent hydrogen, C1-C6 alkyl, halo-C1-C6 alkyl, phenyl-C1-C3 alkyl, or heteroaryl;

[0112] Y can independently represent hydrogen, C2-C6 alkynyl, C1-C6 alkyl carbonyl, heteroaryl carbonyl, C1-C6 alkyloxy carbonyl, or -(C1-C3)alkyl-O-(C=O)-O-(C1-C6)alkyl;

[0113] r represents 0, 1, or 2;

[0114] m represents 0, 1, or 2;

[0115] Wherein, the "heterocyclic group" refers to The term "heteroaryl" refers to The aforementioned group is unsubstituted or substituted by at least one (e.g., 1, 2, 3, 4, 5) group selected from C1-C6 alkyl groups; R' represents C1-C6 alkyl.

[0116] In another preferred embodiment, Z1 represents halogen, C1-C6 alkoxy, or C1-C6 alkylthio.

[0117] Z2 represents C1-C6 alkyl, halo-C1-C6 alkyl, and C1-C6 alkylsulfonyl;

[0118] X independently represents unsubstituted or substituted components. R 11 Each of these independently represents hydrogen, halogen, cyano, NH2, unsubstituted or R-substituted. 13 Arbitrarily substituted C1-C6 alkyl groups, unsubstituted or R 14Arbitrarily substituted C3-C6 cycloalkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 alkoxy, C1-C6 alkoxy-C1-C3 alkyl, C1-C6 alkyl carbonyl amino;

[0119] R 12 Each of these can be independently represented as C1-C6 alkyl, C3-C6 cycloalkyl, C1-C6 alkoxy-C1-C3 alkyl, phenyl, and benzyloxy-C1-C3 alkyl.

[0120] R 13 R 14 Each of these can independently represent halogen, cyano, C1-C6 alkyl, and phenyl groups;

[0121] Q represents cyano group, cyano C1-C3 alkyl group, and N(R) group, respectively. 51 )2,-(C1-C3)alkyl-N(R 51 )2,-(C1-C3)alkyl-N + (R 51 )3, CON(R) 51 )2,-(C1-C3)alkyl-CON(R 51 )2, OR 52 ,-(C1-C3)alkyl-OR 52 COR 52 ,-(C1-C3)alkyl-COR 52 ,-(C1-C3)alkyl-COOR 52 ,-(C1-C3)alkyl-OCOR 52 ,Si(R 52 )3,-(C1-C3)alkyl-O-Si(R 52 )3,-(C1-C3)alkyl-ON=C(R 52 2,-(C1-C3)alkyl-S(O) m -(C1-C6)alkyl, C1-C6alkyl, halo-C1-C6alkyl, C2-C6alkenyl, C2-C6ynyl, halo-C2-C6alkenyl, halo-C2-C6ynyl, unsubstituted or substituted C3-C6 cycloalkyl, C3-C6 cycloalkyl-C1-C3alkyl, unsubstituted or substituted heterocyclic, phenyl, heteroaryl, heterocyclic C1-C3alkyl, phenyl C1-C3alkyl, heteroaryl C1-C3alkyl;

[0122] R 51 Each of these can be independently represented as hydrogen, C1-C6 alkyl, or halo-C1-C6 alkyl.

[0123] R 52Each of these can be independently represented as hydrogen, C1-C6 alkyl groups with or without halogens, phenyl, phenyl-C1-C3 alkyl groups, or heteroaryl groups.

[0124] Y can independently represent hydrogen, C1-C6 alkyl with or without halogen, C2-C6 alkenyl, C2-C6 alkynyl, cyanoC1-C3 alkyl, C1-C6 alkyl carbonyl, benzyl, phenyl carbonyl, heterocyclic carbonyl, heteroaryl carbonyl, C1-C6 alkyloxy carbonyl, and -(C1-C3)alkyl-O-(C=O)-O-(C1-C6)alkyl;

[0125] r represents 2;

[0126] m represents 0, 1, or 2;

[0127] Wherein, the "heterocyclic group" refers to The term "heteroaryl" refers to The aforementioned group is unsubstituted or substituted by at least one group selected from C1-C6 alkyl groups; R' represents C1-C6 alkyl.

[0128] The R-configuration compound of the present invention, based on the content of stereoisomers having R and S configurations at the stated position (*), has a stereochemical purity of 60-100% (R), preferably 70-100% (R), more preferably 80-100% (R), further preferably 90-100% (R), and even more preferably 95-100% (R). Wherein, "stereochemical purity" refers to the percentage of the amount of the stereoisomer relative to the total amount of stereoisomers having a chiral center.

[0129] Furthermore, the salts mentioned are those commonly used in pesticides, for example, they can be formulated as metal salts, amine salts, sulfonium salts, or phosphorus salts. These salts are also included in this invention whenever they are used as herbicides for agricultural or horticultural purposes. In this invention, the salts of the compounds are preferably in the form of their respective alkali metal salts, alkaline earth metal salts, or ammonium salts (such as dimethylammonium salt, triethanolamine salt, isopropylamine salt, choline, etc.), more preferably in the form of their respective alkali metal salts, more preferably in the form of their respective sodium or potassium salts, and most preferably in the form of their respective sodium salts.

[0130] Solvates of the compounds of this invention are also included in this invention.

[0131] Unless otherwise specified, the technical terms used in this invention, whether used alone or in compound terms, refer to a "heterocyclic group" having, for example, 0, 1, or 2 oxo groups. The term "aryl" refers to, for example, phenyl, naphthyl, ... The term "heteroaryl" refers to an aromatic cyclic group containing, for example, 3 to 6 (3, 4, 5, 6) ring atoms and which can also be fused through a benzo[a] ring, wherein 1 to 4 (1, 2, 3, 4) heteroatoms in the ring atoms are selected from oxygen, nitrogen, and sulfur, for example... The aforementioned groups are unsubstituted or selected from halogens, nitro, amino, cyano, cyanothio, cyanoalkyl, mercapto, hydroxy, hydroxyalkyl, carboxyl, formyl, trialkylsilyl, dialkylphosphonyl, unsubstituted or substituted heterocyclic groups, heterocyclic alkyl groups, aryl, arylalkyl, heteroaryl or heteroarylalkyl, alkyl groups containing or not containing halogens, alkenyl, ynyl, cycloalkyl, cycloalkenyl, cycloalkylalkyl, alkyl-substituted cycloalkyl, OR", SR", -alkyl-OR", -O-alkyl-OR", -alkyl-SR", COR", -alkyl-COR", -O-alkyl-COR", COOR", -alkyl-COOR". The amino, aminocarbonyl, aminocarbonylalkyl, or aminosulfonyl group is substituted by at least one (e.g., 1, 2, 3, 4, or 5) of an amino group, aminocarbonyl, aminocarbonylalkyl, or aminosulfonyl group selected from one or two of the R, COR, SO2R, or OR groups, with or without halogen, or the two adjacent substitution positions are connected to the -OCH2CH2-, -OCH2O-, -OCH2CH2O-, or -CH=CH-CH=CH- group to form a ring;

[0132] "R" can independently represent alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl, and unsubstituted or substituted heterocyclic, heterocyclic alkyl, aryl, arylalkyl, heteroaryl or heteroarylalkyl.

[0133] Preferably, the aforementioned group is unsubstituted or selected from halogen, nitro, amino, cyano, cyanothio, cyanoC1-C6 alkyl, mercapto, hydroxy, hydroxyC1-C6 alkyl, carboxyl, formyl, triC1-C6 alkylsilyl, diC1-C6 alkylphosphono, unsubstituted or substituted heterocyclic group, heterocyclic C1-C6 alkyl, aryl, arylC1-C6 alkyl, heteroaryl or heteroarylC1-C6 alkyl, with or without halogenation. Halogenated C1-C6 alkyl, C2-C6 alkenyl, C2-C6 ynyl, C3-C6 cycloalkyl, C3-C6 cycloalkenyl, C3-C6 cycloalkyl C1-C6 alkyl, C1-C6 alkyl-substituted C3-C6 cycloalkyl, OR”, SR”, -(C1-C6)alkyl-OR”, -O-(C1-C6)alkyl-OR”, -(C1-C6)alkyl-SR”, COR”, -(C1-C 6) Alkyl-COR”, -O-(C1-C6)alkyl-COR”, COOR”, -(C1-C6)alkyl-COOR”, -O-(C1-C6)alkyl-COOR”, COSR”, SOR”, SO2R”, -O-SO2R”, -(C1-C6)alkyl-SO2R”, OCOR”, -(C1-C6)alkyl-OCOR” or SCOR” is substituted by at least one (e.g., 1, 2, 3, 4 or 5) of an amino, aminocarbonyl, aminocarbonyl C1-C6 alkyl or aminosulfonyl group selected from one or two of R”, COR”, SO2R” or OR” containing or not containing halogen, or two adjacent substitution positions are connected to -OCH2CH2-, -OCH2O-, -OCH2CH2O- or -CH=CH-CH=CH- group to form a ring;

[0134] "R" can independently represent C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl-C1-C6 alkyl, C3-C6 cycloalkenyl, and unsubstituted or substituted heterocyclic groups, heterocyclic C1-C6 alkyl groups, aryl, aryl C1-C6 alkyl groups, heteroaryl or heteroaryl C1-C6 alkyl groups.

[0135] More preferably, the "heterocyclic group" refers to a group having, for example, 0, 1, or 2 oxo groups. The term "aryl" refers to, for example, phenyl, naphthyl, ... The term "heteroaryl" refers to, for example... The aforementioned groups are unsubstituted or substituted by at least one (e.g., 1, 2, 3, 4, or 5) groups selected from halogen, nitro, amino, cyano, cyanothio, cyanoC1-C6 alkyl, mercapto, hydroxy, hydroxyC1-C6 alkyl, carboxyl, formyl, unsubstituted or substituted by at least one (e.g., 1, 2, 3, 4, or 5) groups selected from halogen, hydroxy, nitro, cyano, amino, carboxyl, and halogen-containing or non-halogenated groups (C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C1-C6 alkoxy, C1-C6 alkoxycarbonyl, C1-C6 alkyl acyl, C1-C6 alkyl acyloxy, C1-C6 alkylamino, or C1-C6 alkyl sulfonyl). Phenyl or benzyl, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C6 alkyl, C1-C6 alkyl-substituted C3-C6 cycloalkyl, OR”, SR”, -(C1-C6)alkyl-OR”, -O-(C1-C6)alkyl-OR”, -(C1-C6)alkyl-SR”, COR”, -(C1-C6)alkyl-COR”, -O-(C1-C6)alkyl-COR”, COOR”, -(C1-C6)alkyl-COOR”, -O-(C1-C6)alkyl-COOR”, -O-(C1-C6)alkyl-CO OR”, COSR”, SOR”, SO2R”, -O-SO2R”, -(C1-C6)alkyl-SO2R”, OCOR”, -(C1-C6)alkyl-OCOR” or SCOR” are substituted by at least one (e.g., 1, 2, 3, 4, 5) of an amino, aminocarbonyl or aminosulfonyl group selected from one or two groups of R”, COR”, SO2R” or OR” with or without halogen, or two adjacent substitution positions are linked to -OCH2CH2-, -OCH2O-, -OCH2CH2O- or -CH=CH-CH=CH- groups to form a ring;

[0136] R' independently represents hydrogen, nitro, hydroxyl, amino, and C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkenyl, C3-C6 cycloalkyl, C1-C6 alkyl, with or without halogen. C1-C6 alkoxy, C2-C6 alkenyloxy, C2-C6 alkynyloxy, C3-C6 cycloalkyloxy, C1-C6 alkoxy C1-C6 alkyl, C1-C6 alkoxy carbonyl, C1-C6 alkylthiocarbonyl, C1-C6 alkylsulfonyl, C1-C6 alkylsulfonyl C1-C6 alkyl, C1-C6 alkyl carbonyl, C1-C6 alkyl carbonyl C1-C6 alkyl, C1-C6 alkylacyloxy, C1-C6 alkylamino, C1-C6 alkylamino carbonyl, C1-C6 alkoxyamino carbonyl, C1-C6 alkoxy carbonyl C1-C6 alkyl, C1-C 6-alkylaminocarbonyl C1-C6 alkyl, triC1-C6 alkylsilyl or diC1-C6 alkylphosphonoyl, and phenyl or benzyl groups unsubstituted or substituted by at least one (e.g., 1, 2, 3, 4, 5) of a group selected from halogen, hydroxyl, nitro, cyano, amino, carboxyl, or containing or not containing halogen (C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C1-C6 alkoxy, C1-C6 alkoxycarbonyl, C1-C6 alkylacyl, C1-C6 alkylacyloxy, C1-C6 alkylamino or C1-C6 alkylsulfonyl);

[0137] "R" independently represents, respectively, at least one (e.g., 1, 2, 3, 4, or 5) groups selected from C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C1-C6 alkyl, C3-C6 cycloalkyl, and alkyl groups (C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C1-C6 alkoxy, C1-C6 alkoxycarbonyl, C1-C6 alkylacyl, C1-C6 alkylacyloxy, C1-C6 alkylamino, or C1-C6 alkylsulfonyl). Phenyl or benzyl.

[0138] In the definitions of compounds shown in the above general formulas and in all the following structural formulas, the technical terms used, whether alone or in compound terms, represent the following substituents: alkyl groups having more than two carbon atoms can be straight-chain or branched. For example, the compound term "-alkyl-OR". 1The alkyl group can be -CH2-, -CH2CH2-, -CH(CH3)-, -C(CH3)2-, etc. The alkyl group is, for example, C1 alkyl-methyl; C2 alkyl-ethyl; C3 alkyl-propyl such as n-propyl or isopropyl; C4 alkyl-butyl such as n-butyl, isobutyl, tert-butyl, or 2-butyl; C5 alkyl-pentyl such as n-pentyl; C6 alkyl-hexyl such as n-hexyl, isohexyl, and 1,3-dimethylbutyl. Similarly, the alkenyl group is, for example, allyl, 1-methylprop-2-en-1-yl, 2-methylprop-2-en-1-yl, but-2-en-1-yl, but-3-en-1-yl, 1-methylbut-3- -en-1-yl and 1-methylbut-2-en-1-yl. Alkynes are, for example, propargyl, but-2-yn-1-yl, but-3-yn-1-yl, and 1-methylbut-3-yn-1-yl. Multiple bonds: At least one (e.g., 1, 2, or 3) multiple bonds can be in any position in each unsaturated group. Cycloalkyl: A carbocyclic saturated ring system having, for example, three to six carbon atoms, such as cyclopropyl, cyclobutyl, cyclopentyl, or cyclohexyl. Similarly, cycloalkenyl: A monocyclic alkenyl having, for example, three to six carbon ring members, such as cyclopropenyl, cyclobutenyl, cyclopentenyl, and cyclohexenyl, wherein the double bond can be in any position. Halogens: Fluorine, chlorine, bromine, or iodine.

[0139] If a group is substituted by another group, this should be understood to mean that the group is substituted by one or more identical or different groups selected from those groups mentioned. Furthermore, the identical or different substitution characters contained in the identical or different substituents are chosen independently and may be identical or different. This also applies to ring systems formed from different atoms and units. Meanwhile, the scope of the claims excludes compounds that are chemically unstable under standard conditions, as known to those skilled in the art.

[0140] Furthermore, unless otherwise specified, in this invention, the foregoing qualifiers of multiple parallel substituents (separated by "," or "or") have a limiting effect on each subsequent substituent. For example, in "alkyl, alkenyl, ynyl, cycloalkyl, cycloalkenyl, cycloalkylalkyl, or cycloalkenylalkyl which are free from or contain halogens," the phrase "free from or contain halogens" limits each subsequent group "alkyl," "alkenyl," "ynyl," "cycloalkyl," "cycloalkenyl," "cycloalkylalkyl," or "cycloalkenylalkyl." "Alkylamino" refers to an amino group that is mono- or di-substituted by an alkyl group; other substituted amino groups are defined similarly. Groups without a specific connection position (including heterocyclic, aryl, and heteroaryl groups) can be connected at any position, including positions connected to C or N. If it is substituted, the substituent can also be substituted at any position, as long as it conforms to the rules of chemical bond connection. For example, a heteroaryl group substituted by one methyl group. Can represent wait.

[0141] Enantiomers can be obtained from mixtures prepared by conventional separation methods, such as chromatographic separation. They can also be selectively prepared using stereoselective reactions and optically active starting materials and / or auxiliaries.

[0142] In one specific embodiment, the method for preparing the arylformamide compound containing a chiral sulfur oxide or its salt includes the following steps:

[0143] (1) Using compounds as shown in general formula I' Compounds of general formula I are prepared by liquid phase separation (e.g., chiral HPLC resolution); or,

[0144] (2) Using compounds as shown in general formula I” Compounds of general formula I were prepared in the presence of peroxides (such as H2O2) and Jacobsen catalysts.

[0145] Preferably, the reaction (2) is carried out in the presence of a solvent selected from at least one of methanol, ethanol, isopropanol, acetonitrile, dichloroethane, DMF, DMSO, dioxane, dichloromethane, or ethyl acetate.

[0146] A herbicidal composition comprising (i) the arylformamide compound containing a chiral sulfur oxide or a salt thereof; preferably, further comprising (ii) one or more additional herbicides and / or safeners; more preferably, further comprising (iii) an agriculturally acceptable formulation adjuvant.

[0147] A method for controlling weeds includes applying a herbicidal effective amount of at least one of the said chiral sulfur oxide-containing arylformamide compounds or their salts, or the said herbicide composition, to plants or weedy areas.

[0148] The use of at least one of the chiral sulfur oxide-containing aryl formamide compounds or their salts, or the herbicide composition thereof, in controlling weeds, preferably, the use of the chiral sulfur oxide-containing aryl formamide compounds or their salts in controlling weeds in useful crops, wherein the useful crops are transgenic crops or crops treated with genome editing technology.

[0149] For many economically important monocotyledonous and dicotyledonous pests, the compounds of Formula I of this invention exhibit outstanding herbicidal activity. The active substances of this invention are also effective against perennial weeds that grow from rhizomes, stems, or other perennial organs and are difficult to control. In this regard, it is generally not important whether the substance is used before sowing, before germination, or after germination. Representative examples of monocotyledonous and dicotyledonous weed populations that can be controlled by the compounds of this invention are specifically mentioned, without limiting the specific species. Examples of weed species to which the active substances are effective include monocotyledons: annuals of *Oat*, *Rye*, *Grass*, *Alopecurus*, *Fararis*, *Barnyardgrass*, *Digitaria*, *Setaria*, and *Sedge*, and perennials of *Agrostis*, *Bermudagrass*, *Imperata*, and *Sorghum*, as well as perennials of *Sedge*.

[0150] Regarding dicotyledonous weed species, its effects can be extended to annual species such as *Galium aparine*, *Viola*, *Veronica*, *Sesamum indicum*, *Stellaria*, *Amaranthus*, *Sinapis*, *Ipomoea*, *Heliotropium*, *Chaenomeles*, and *Abutilon*, and perennial weeds such as *Convolvulus*, *Thistle*, *Rumex*, and *Artemisia*. The active substances of this invention effectively control harmful plants such as barnyard grass, *Sagittaria*, *Alisma*, *Eupatorium*, *Sedum*, and *Sedge* under the undetermined condition of rice sowing. If the compounds of this invention are applied to the soil surface before germination, weed seedlings can be completely prevented before they emerge, or growth can be stopped when the weeds develop cotyledons, eventually leading to their complete death after three to four weeks. The compounds of this invention exhibit particularly excellent activity against the following plants: *Apira*, *Sesamum indicum*, *Polygonum cuspidatum*, *Stellaria*, *Veronica ivy*, *Veronica arabiculata*, *Viola tricolor* and *Amaranthus*, *Galium aparine*, and *Kochia scoparia*.

[0151] While the compounds of this invention exhibit excellent herbicidal activity against both monocot and dicot weeds, they cause little to no damage to important economic crops such as wheat, barley, rye, rice, corn, sugar beets, cotton, and soybeans. They are particularly compatible with cereal crops, such as wheat, barley, and corn, especially wheat. Therefore, the compounds of this invention are highly suitable for the selective control of unwanted plants in agricultural or ornamental crops.

[0152] Due to their herbicidal properties, these active substances can be used to control harmful plants in known or future genetically engineered plant cultivation. Transgenic plants typically possess superior traits, such as resistance to specific insecticides, particularly specific herbicides, and resistance to plant diseases or pathogenic microorganisms, such as specific insects or fungi, bacteria, or viruses. Other specific traits relate to conditions such as quantity, quality, storage stability, composition, and special components of the product. Thus, it is known that transgenic plant products have increased starch content or improved starch quality or different fatty acid compositions.

[0153] The compounds of Formula I of the present invention, or salts thereof, are preferably used in the cultivation of economically important genetically modified crops and ornamental plants, such as cereals, including wheat, barley, rye, oats, millet, rice, cassava, and corn, or in the cultivation of sugar beets, cotton, soybeans, rapeseed, potatoes, tomatoes, peas, and other vegetable plants. The compounds of Formula I are preferably used as herbicides for the cultivation of useful plants that are resistant or have been genetically engineered to resist the toxic effects of the herbicides.

[0154] Traditional methods for breeding plants with improved morphology compared to known plants include, for example, conventional mating methods and mutant breeding. In other words, new plants with improved traits can be obtained using genetic engineering methods (see, for example, EP-0221044 A, EP-0131624 A). Several methods have been described, for example:

[0155] - To improve starch synthesis in plants, genetic engineering is used to modify crop plants (e.g., WO 92 / 11376, WO92 / 14827, WO 91 / 19806);

[0156] - Transgenic crop plants resistant to specific herbicides, such as glufosinate-methyl (e.g., EP-0242236A, EP-0242246 A), glyphosate-based herbicides (WO 92 / 00377), or sulfonylurea herbicides (EP-0257993A, US-5013659 A);

[0157] - For example, genetically modified cotton plants can produce Bt toxins, which can defend against certain pests (EP-0142924A, EP-0193259A).

[0158] - A genetically modified crop plant with improved fatty acid composition (WO91 / 13972).

[0159] Many molecular biotechnologies for preparing transgenic plants with improved traits are known (see, for example, Sambrook et al., 1989, Molecular Amplification, Laboratory Manual, 2nd ed., Cold Spring Harbor Laboratory, Cold Spring Harbor, New York; or Winnacker, “Gene and Cloning,” VCH Weinheim, 2nd ed., 1996; or Christou, “Trends in Plant Science,” 1 (1996) 423-431). To perform genetic engineering operations, nucleic acid molecules may be introduced into plasmids, resulting in mutations or sequence alterations through DNA sequence recombination. Using standard methods, such as exchanging substrates, removing portions of the sequence, or adding natural or synthetic sequences, can be employed. To link DNA fragments together, it is possible to attach conjugates or linkers to the fragments.

[0160] Plant cells containing reduced-activity gene products can be prepared by methods such as expressing at least one appropriate antisense RNA or sense RNA to achieve co-inhibition, or by expressing at least one appropriately constructed ribozyme that specifically cleaves the transcript of the aforementioned gene product.

[0161] For this purpose, it is possible to use a DNA molecule containing the entire coding sequence of the gene product, including any possible flanking sequences, or a DNA molecule containing only a portion of the coding sequence, which must be long enough to achieve an antisense effect in the cell. Alternatively, a sequence that is highly homologous to but not identical to the coding sequence of the gene product can also be used.

[0162] When nucleic acid molecules are expressed in plants, the synthesized proteins can be localized in any desired plant cell compartment. However, to localize in a specific compartment, it is possible, for example, to link the coding region to a DNA sequence to ensure localization at a specific location. These sequences are known to those skilled in the art (see, for example, Braun et al., EMBO J.11 (1992) 3219-3227; Wolter et al., Proc. Natl. Acad. Sci. USA 85 (1988), 846-850; Sonnewald et al. Plant J.1 (1991), 95-106).

[0163] Using known techniques, transgenic plant cells can be recombined into the entire plant. Transgenic plants can be any desired plant variety, i.e., monocots and dicots. In this way, it is possible to obtain transgenic plants with improved traits by overexpressing, inhibiting or suppressing homologous (=natural) genes or gene sequences, or by expressing heterologous (=external) genes or gene sequences.

[0164] When the active substances of this invention are used on genetically modified crops, in addition to the inhibitory effect on harmful plants observed in other crops, they often exhibit specific effects on the corresponding genetically modified crops. For example, they can improve or expand the range of weed control, improve the application rate, preferably combine the herbicide resistance of the genetically modified crop with the performance of the herbicide, and affect the growth and yield of the genetically modified crop. Therefore, this invention also provides the use of the compounds as herbicides to control harmful plants in genetically modified crop plants.

[0165] Furthermore, the compounds of this invention can significantly regulate crop growth. By modulating plant metabolism, these compounds can be used to directionally control plant components and promote harvesting, for example, by causing plant drying and dwarfing. They are also suitable for regulating and inhibiting unwanted plant growth without disrupting crop growth. Inhibiting plant growth plays a crucial role in many monocot and dicot crops because it can reduce or completely prevent lodging.

[0166] The compounds of the present invention can be applied using common formulations, including wettable powders, concentrated emulsions, sprayable solutions, powders, or granules. Thus, the present invention also provides herbicide compositions comprising compounds of formula I. Compounds of formula I can be formulated in various ways depending on typical biological and / or chemical physical parameters. Examples of suitable formulation choices include: wettable powders (WP), water-soluble powders (SP), water-soluble concentrates, concentrated emulsions (EC), emulsions such as oil dispersed in water and water dispersed in oil (EW), sprayable solutions, suspension concentrates (SC), dispersible oil suspensions (OD), suspensions diluted with oil or water, solutions miscible with oil, powders (DP), capsule suspensions (CS), seeddressing compositions, granules for broadcasting and soil application, spray granules, coating granules and absorbent granules, water-dispersible granules (WG), water-soluble granules (SG), ULV (ultra-low volume) formulations, microcapsules, and wax products. These individual formulation types are known and described in the following literature, for example, Winnacker-Küchler, “Chemische Techonologie” [Chemical Processes], Vol. 7, C. Hauser Verlag Munich, 4th ed. 1986; Wade van Valkenburg, “Pesticide Formulations”, Marcel Dekker, NY, 1973; K. Martens, “Spray Drying” Handbook, 3rd ed. 1979, G. Goodwin Ltd. London.

[0167] Necessary formulation adjuvants, such as inert substances, surfactants, solvents, and other additives, are also known and described in the following documents, for example, Watkins's "Handbook of Powder Diluents, Insecticides, and Carriers," 2nd ed., Darland, Caldwell, NJ; Hv01phen's "Introduction to Clay Colloid Chemistry," 2nd ed., J. Wiley and Sons, NY; C. Marsden's "Solvent Guide," 2nd ed., Interscience, NY 1963; McCutcheon's "Annual Report on Detergents and Emulsifiers," MC Publishing, Ridgewood, NJ; Sisley and Wood, "Encyclopedia of Surfactants," Chemical Publishing, NY 1964; of [Ethylene oxide adduct surfactants], Wiss. Verlagagesell. Stuttgart 1976; Winnacker-Küchler's "Chemische Technologie" [Chemical Processes], Vol. 7, C. Hauser Verlag Munich, 4th edition 1986.

[0168] Wettable powders are uniformly dispersible in water and, in addition to the active ingredient, include diluents or inert substances, ionic and nonionic surfactants (wetting agents, dispersants), such as polyethoxyalkylphenols, polyethoxy fatty alcohols, polyoxyethyl aliphatic amines, fatty alcohol polyethylene glycol ether sulfates, alkyl sulfonates, alkyl phenyl sulfonates, sodium lignosulfonate, sodium 2,2'-dinaphthylmethane-6,6'-disulfonate, sodium dibutylnaphthalenesulfonate, or sodium oleoylmethyl taurate. To prepare wettable powders, the active ingredient of the herbicide is finely ground, for example using common equipment such as hammer mills, fan mills, and jet mills, while adjuvants are mixed in simultaneously or sequentially.

[0169] Concentrated emulsions are prepared by dissolving active ingredients in an organic solvent, such as butanol, cyclohexanone, dimethylformamide, xylene, or a mixture of higher-boiling aromatic compounds or hydrocarbons, and then adding one or more ionic and / or nonionic surfactants (emulsifiers). Examples of emulsifiers that can be used include, for example, calcium alkylaryl sulfonate of calcium dodecylbenzenesulfonate, or nonionic emulsifiers such as fatty acid polyethylene glycol esters, alkyl aromatic polyethylene glycol ethers, fatty alcohol polyethylene glycol ethers, propylene oxide-ethylene oxide condensation products, alkyl polyethers, sorbitan esters such as sorbitan fatty acid esters, or polyethylene oxide sorbitan esters such as polyethylene oxide sorbitan fatty acid esters.

[0170] The active substance and finely ground solid material are ground to obtain a powder. The solid material may be talc, natural clay such as kaolin, bentonite, and pyrophyllite, or diatomaceous earth. A water- or oil-based suspension may be prepared, for example, by wet grinding using a commercially available glass bead mill, with or without the addition of a surfactant of the other formulation type mentioned above.

[0171] Emulsions, such as oil-in-water (EW) emulsions, can be prepared using an aqueous organic solvent, a stirrer, a colloid mill, and / or a static mixer, and if necessary, by adding a surfactant of another formulation type as described above.

[0172] Granules can be prepared by spraying the active material onto an adsorbent and granulating it using an inert material, or by concentrating the active material onto the surface of a carrier such as sand or kaolinite and granulating it using a binder such as polyvinyl alcohol, sodium polyacrylate, or mineral oil. Suitable active materials can be granulated using methods for preparing fertilizer granules, and fertilizers can be mixed in if necessary. Aqueous suspension granules can be prepared using conventional methods such as spray-drying, fluidized bed granulation, disc granulation, mixing using a high-speed mixer, and extrusion without solid inert material.

[0173] For methods of preparing granules using grinding discs, fluidized beds, extruders, and spraying, see the following processes, for example, “Spray Drying Handbook,” 3rd edition, 1979, G. Goodwin Ltd., London; J.E. Browning, “Agglomeration,” Chemicals and Engineering, 1967, 147ff; and “Perry’s Chemical Engineer’s Handbook,” 5th edition, McGraw-Hill, New York, 1973, 8–57. For information on formulations of crop protection products, see, for example, G.K. C. Lingman, “Weed Control as a Science,” John Wiley and Sons, New York, 1961, 81–96; and JD. F. Greyer, SAEvans, “Weed Control Handbook,” 5th edition, Blackwell Scientific Rublications, Oxford University Press, 1968, 101–103.

[0174] Agricultural chemical formulations typically contain 0.1% to 99%, particularly 0.1% to 95%, of active ingredient Formula I by weight. The concentration of active ingredient in wettable powders is, for example, from about 10% to 99% by weight, with the usual formulation components constituting the remainder to 100% by weight. The concentration of active ingredient in concentrated emulsions can be from about 1% to 90% by weight, preferably 5% to 80%. Powder formulations contain 1% to 30% active ingredient by weight, typically preferably 5% to 20% by weight; however, sprayable solutions contain about 0.05% to 80% by weight, preferably 2% to 50% by weight. The content of active ingredient in aqueous suspension granules depends primarily on whether the active ingredient is liquid or solid, and on the adjuvants, fillers, etc., used during granulation. The content of active ingredient in aqueous suspension granules is, for example, between 1% and 95% by weight, preferably between 10% and 80% by weight.

[0175] The formulation of the active substance may also include thickeners, wetting agents, dispersants, emulsifiers, penetrants, preservatives, antifreeze agents, solvents, fillers, carriers, colorants, defoamers, evaporation inhibitors, and pH and viscosity adjusters that are commonly used in all cases.

[0176] Based on these formulations, they may also be mixed with other insecticidal active substances such as insecticides, acaricides, herbicides and fungicides, or with safeners, fertilizers and / or plant growth regulators. The mixing method may be pre-mixed or bottled.

[0177] Suitable active substances that can be mixed with the active substances of the present invention in compound formulations or tank-mixed formulations include, for example, known substances in the "World Encyclopedia of New Pesticide Varieties Technology", China Agricultural Science and Technology Press, 2010.9 and the literature cited herein. For example, the following herbicidal active substances can be mixed with mixtures of Formula I (Note: the name of the compound, either the common name according to the International Organization for Standardization (ISO) or the chemical name, with a code where appropriate): acetochlor, butachlor, metolachlor, isopropachlor, isopropachlor, succinyl-metolachlor, propachlor, chlorpyrifos, chlorpyrifos, naphthalenepropanoyl-methyl, R-L-naphthalenepropanoyl-methyl, propachlor, benzylthiamethoxam, bisbenzylthiamethoxam, pyrifluquinazon, chlorpyrifos, flubutyroxychlor, brobutyroxychlor, dimethoate, high-efficiency dimethoate, ethoxybenzyl-methyl, flubutyroxychlor, methoxythiamethoxam, pyrifluquinazon, isoxachlor, high-efficiency methylparaben, high-efficiency methylparaben. Acetaminophen, clethodim, butyrazosulfuron, cyprochloraz, flusulfuron, heptanosulfuron, isobutyrazosulfuron, propyzamide, terbutyrazosulfuron, methylparaben, metolachlor, methylcyclohexane, chlorpyrifos, propyzamide, pendimethalin, carbaryl, succinylmethrin, tricyclomethrin, butyrazosulfuron, succinylmethrin, bensulfuron-methyl, naphthylmethrin, acetochlor, naphthylmethrin, thiamethoxam, pyrimethanil, bensulfuron-methyl, chlorpyrifos, butyrazosulfuron, flupyrazole, atrazine, simazine, promethazine, cypermethrin, cypermethrin, atrazine, pyrazosulfuron, isopropazine, flumethrin, terbutyraz, terbutyraz, triazine flumethrin, cyprochlorazine, glyphosate, chlorpyrifos Phosphatidylcholine, Simazine, Ziziphus jujuba, Dichlorvos, Isoamyl acetate, Cyprodinil, Atrazine, Butyraz, Butyraz, Terbutaline, Methoxypropazine, Cypermethrin, Herbicides, Clonazine, Atrazine, Methoxypropazine, Glycyrrhizin, Cyanobacterium trioxide, Indaziflam, Greensulfuron, Methsulfuron-methyl, Benzylsulfuron, Chlorpyrifos, Bensulfuron-methyl, Thisulfuron-methyl, Pyrimisulfuron-methyl, Methiosulfuron-methyl, Sodium formamide sulfuron, Ethersulfuron-methyl, Etherbensulfuron-methyl, Methsulfuron-methyl, Nicosulfuron-methyl, Aminosulfuron-methyl, Acylsulfuron-methyl, Ethoxysulfuron-methyl, Cyprosulfuron-methyl, Sulfadiazine, Tetraazolidinylsulfuron, Pyrimisulfuron, Monosulfuron-methyl, Fluazolidinylsulfuron, Flupyrimisulfuron, Flupyrimisulfuron, Epimethrin Sulfuric acid, pyrazosulfuron, flusulfuron, propanil, trifluprosulfuron, sulfonylsulfuron, trifluralin, flusulfanil, trifluralin, mesosulfuron sodium salt, flupyrsulfuron, thiosulfuron, pyrimethanil, propyrisulfuron, pyrazosulfuron, trifluralin, flusulfanilamide, quizalofop-p-ethyl, ethoxysulfuron, glufosinate, bensulfuron, chlorfluazuron ethyl, methylfluzoxystrobin, trifluralin, methoxysulfuron, trifluralin, flufenoxuron, flufenoxuron, oxysulfuron, metolachlor, sulfadiazine, flufenoxuron, oxysulfuron, metolachlor, flufenoxuron, flufenoxuron, halosafen, chlormequat chloride, isoproturon, linuron, diuronSaprolegnia, fluroxypyr, bensulfuron, methyl bensulfuron, bensulfuron, sulfothiamethoxam, isoxaflutole, terbutaline, clodinafop-methyl, chlorobromosulfuron, methyl methoxysulfuron, methyl methoxysulfuron, bromosulfuron, methoxysulfuron, chlorpyrifos, metribuzin, cycloroxysulfuron, felsulfuron, flusulfuron, glufosinate, fensulfuron, cyproconazole, thiamethoxam, fensulfuron, chlorpyrifos, methamidophos, thiamethoxam, trimethourea, oxazolium, Monisouron, Anisuron, Methiuron, Chloreturon, tetraflufenozide, betaine, betaine-ethyl, betaine, sulfonamide, terbutaline, fensulfuron-methyl, fensulfuron-methyl, fensulfuron-methyl, fensulfuron-methyl, chlorpyrifos, carboxazo le, Chlorprocarb, Fenasulam, BCPC, CPPC, Carbasulam, Butyrazosulfan, Clethodim, Metrazine, Clethodim, Wild Grass, Permethrin, Clethodim, Barnyardgrass, Cypermethrin, Oat Grass, Dimethoate, Ethylmethazine, Methiobencarb, Clethodim, Benzoate, Methiobencarb, Thionylmethazine, Methiobencarb, 2,4-D Butyl Acetate, 2,4-D Sodium Chloride, 2,4-D Isooctyl Acetate, 2,4-D Sodium Salt, 2,4-D Dimethylamine Salt, 2,4-D Chlorethyl Thiate, 2,4-D Chloride, 2,4-D Propionic Acid, High 2,4-D Propionate, 2,4-D Butyric Acid, 2,4-D Chlorpropionic Acid, 2,4-D Propionate 2,4,5-chlorobutyric acid, 2,4,5-propylpropionic acid, 2,4,5-propylbutyric acid, 2,4,5-chloromethacin, MCPA, dicamba, quizalofop-p-ethyl, cyhalofop-p-ethyl, quizalofop-p-ethyl, quizalofop-p-ethyl, quizalofop-p-ethyl, quizalofop-p-ethyl, quizalofop-p-ethyl, quizalofop-p-ethyl, quizalofop-p-ethyl, quizalofop-p-ethyl, quizalofop-p-ethyl, quizalofop-p-ethyl, cyhalofop-p-ethyl, quizalofop-p-ethyl, quizalofop-p-ethyl, quizalofop-p-ethyl, quizalofop-p-ethyl, quizalofop-p-ethyl, quizalofop-p-ethyl, quizalofop-p-ethyl, quizalofop-p-ethyl, quizalofop-p-ethyl, quizalofop-p-ethyl, quizalofop-p-ethyl, quizalofop-p-ethyl, quizalofop-p-ethyl, quizalofop-p-ethyl, quizalofop-p-ethyl, quizalofop-p-ethyl, quizalofop-p-ethyl, quizalofop-p-ethyl, quizalofop-p-ethyl, quizalofop-p-ethyl, quizalofop-p-ethyl, quizalofop-p-ethyl, quizalofop-p-ethyl, quizalofop-p-ethyl, quizalofop-p-ethyl In, proponitrophenol, glyphosate, barnyardphos, glufosinate, methyl parathion, glyphosate, piperazine, diammonium phosphate, dimethoate, phosmet, fenpropathrin, fenpropathrin, fenpropathrin, dimethoate, fenpropathrin, imidacloprid, imidacloprid acetic acid, imidacloprid quinolinic acid, methoxymethylene, methoxymethylene ammonium salt, imidacloprid acetic acid, imidacloprid, clopyralid, clopyralid isooctyl ester, dichloropyridine acid, aminopyridine acid, trichloropyridine acid, fluthion, haloxypyridine, trichloropyridine phenol, thiamethoxam, flupyridine, clopyralid, flupyridine hydrazone, trichloropyridine butoxyethyl ester, cliodinate, clethodim, thiamethoxam, quizalofop-p-ethyl, cyclobenzanone, butenazine, oxadiazine, pyranazine, buthidazole, cyproconazoleAmetridione, Amibuzin, bromobenzonitrile, octanoyl bromobenzonitrile, octanoyl iodobenzonitrile, iodobenzonitrile, diphenylacetonitrile, bispyribac-sodium, hydroxybispyribac-sodium, Iodobonil, pyrimisulfuron-methyl, diflubenzuron, penoxsulam, sulfadiazine, chlorpyrifos-sulfuron-methyl, dichlorvos-sulfuron-methyl, flumethrin, bispyribac-sodium, pyrimisulfuron-methyl, pyrimisulfuron-methyl, pyrimisulfuron-methyl, bispyribac-sodium, nicosulfuron-methyl, sulfadiazine, Tembotrione, Tefuryltrione, Bicyclopyrone, Ketodpiradox, isoxasulfuron-methyl, isoxasulfuron-methyl, Fenoxasulfone, M ethiozolin, isopropalazine, pyrazosulfuron, pyrazosulfuron, pyrazosulfuron, bensulfuron, pyrazosulfuron, pyrazosulfuron, pyrazosulfuron, pyrazosulfuron, flumetsulam, pyrazosulfuron, pyrazosulfuron, flumethrin, pyrazosulfuron, flupropacil, pyrazosulfuron, pyrazosulfuron, pyrazosulfuron, flupropacil ... Herbicides, fluazinam, methyl methacrylate, tetrazolium chlorpyrifos, flupyridamole, chlorpyrifos, bromochlor, dimethomorph, pyrazosulfuron, cyprodinil, pyrazosulfuron, pyrazosulfuron, pyrazosulfuron, pyrazosulfuron, cyprodinil, pyrazosulfuron, bentazon, pyrazosulfuron, oxadiazon, cyprodinil, isoxadiazon, cyprodinil, isopropyl methoxysulfuron, cyprodinil, indicarb, sodium chlorate Herbicides, trichloroacetic acid, monochloroacetic acid, hexachloroacetone, tetrafluoropropionic acid, forage grass, bromophenol oxime, triazole sulfonate, methomyl, furazolidone, furazolidone, ethoxysulfuron, pyrimethanil, chlorpyrifos, flurfluthrin, barnyardgrass, acrolein, bensulfuron-methyl, metribuzin, oat ester, thiamethoxam, styracil, hydroxylone, methoxybenzone, pyrimethanil, chlorpyrifos, trichloropropionic acid, Al orac, Diethamquat, Etnipromid, Iprymidam, Ipfencarbazone, Thiencarbazone-methyl, Pyrimisulfan, Chlorflurazole, Tripropindan, Sulglycapin, methylsulfuron, Cambendichlor, Cyproterinic acid, Thiamethoxam, cypermethrin, cypermethrin, cypermethrin, cypermethrin, cypermethrin, cypermethrin, cypermethrin, pyrazole cypermethrin, furazolidone, oxadiazon, bis(oxazolyl)acrylic acid, dichloropropenylamine, fluorochloropyridinium, DOW fluorochloropyridinium, UBH-509D489,LS 82-556, KPP-300, NC-324, NC-330, KH-218, DPX-N8189, SC-0744, DOWCO535, D K-8910, V-53482, PP-600, MBH-001, KIH-9201, ET-751, KIH-6127 and KIH-2023. ,

[0178] In the context of this specification, if the abbreviation of the common name of the active compound is used, it includes, in each case, all conventional derivatives, such as esters and salts, and isomers, particularly optical isomers, especially one or more commercially available forms. If the common name indicates an ester or salt, it also includes, in each case, all other conventional derivatives, such as other esters and salts, free acids and neutral compounds, and isomers, particularly optical isomers, especially one or more commercially available forms. The chemical name of the compound given indicates at least one compound covered by the common name, which is generally preferred. In the case of sulfonamides such as sulfonylureas, the salt also includes salts formed by the exchange of hydrogen atoms in the sulfonamide group with a cation. For example, 2,4-D or 2,4-D butyric acid derivatives include, but are not limited to: 2,4-D or 2,4-D butyrate salts such as sodium salt, potassium salt, dimethylammonium salt, triethanolamine salt, isopropylamine salt, choline, etc., and 2,4-D or 2,4-D butyrate esters such as methyl ester, ethyl ester, butyl ester, isooctyl ester, etc.; 2,4-methylchloro derivatives include, but are not limited to: 2,4-methylchloro sodium salt, potassium salt, dimethylammonium salt, isopropylamine salt, etc., and 2,4-methylchloro methyl ester, ethyl ester, isooctyl ester, ethyl thioester, etc.

[0179] When used, commercially available formulations should be diluted in a common manner if necessary, such as with water for wettable powders, concentrated emulsions, suspensions, and granules suspended in water. Powders, granules for soil application, or solutions for broadcasting and spraying generally do not require further dilution with an inert substance before use. The required dosage of Formula I compound varies with external conditions, such as temperature, humidity, and the nature of the herbicide used. It can vary considerably, for example, from 0.001 to 1.0 kg / ha, or more active ingredient, but is preferably from 0.005 to 750 g / ha, particularly from 0.005 to 500 g / ha. Detailed Implementation

[0180] The following examples are for illustrative purposes only and should not be construed as limiting the invention in any way. The scope of protection of this invention is defined by the claims.

[0181] Given the economic efficiency and diversity of the compounds, we preferentially synthesized a number of compounds, some of which are listed in Tables 1-2 below. The specific compound structures and corresponding compound information are shown in Tables 1-2. The compounds in Tables 1-2 are only for better illustration of the present invention and do not limit the invention. Those skilled in the art should not interpret this as limiting the scope of the above-mentioned subject matter of the invention to the following compounds.

[0182] Table 1 Structure of Compound I

[0183]

[0184]

[0185]

[0186]

[0187]

[0188]

[0189]

[0190]

[0191]

[0192]

[0193]

[0194]

[0195]

[0196]

[0197]

[0198]

[0199]

[0200]

[0201]

[0202]

[0203]

[0204]

[0205]

[0206]

[0207]

[0208]

[0209]

[0210]

[0211]

[0212]

[0213]

[0214]

[0215]

[0216]

[0217]

[0218]

[0219]

[0220]

[0221]

[0222]

[0223]

[0224]

[0225]

[0226]

[0227]

[0228]

[0229]

[0230]

[0231]

[0232]

[0233]

[0234] Table 2 Compound I 1 HNMR data

[0235]

[0236]

[0237]

[0238]

[0239]

[0240]

[0241]

[0242]

[0243]

[0244]

[0245]

[0246]

[0247]

[0248]

[0249]

[0250]

[0251] Several methods for preparing the compounds of the present invention are described in detail in the following schemes and examples. The raw materials can be commercially available or prepared by methods known in the literature or as detailed in the description. Those skilled in the art will understand that other synthetic routes can also be used to synthesize the compounds of the present invention. Although specific raw materials and conditions in the synthetic routes have been described below, they can be easily replaced with other similar raw materials and conditions. Such variations or modifications to the preparation methods of the present invention, such as various isomers of the compounds, are all included within the scope of the present invention. Furthermore, the preparation methods described below can be further modified according to the disclosure of the present invention using conventional chemical methods well known to those skilled in the art. For example, protecting appropriate groups during the reaction process, etc.

[0252] The following method examples are provided to further illustrate the preparation methods of the present invention. The specific substances, types, and conditions used are intended to further explain the invention and are not intended to limit its reasonable scope. The reagents used in the synthetic compounds shown in the table below are either commercially available or can be easily prepared by those skilled in the art.

[0253] Examples of representative compounds are given below. The synthesis methods of other compounds are similar and will not be described in detail here.

[0254] 1. Synthesis of Compound 3

[0255] (1) Add a (3g, 16mmol, 1.0eq) and NaOH (0.72g, 18mmol, 1.1eq) sequentially to 30 mL of DMF. Then, add n-PrSH (1.28g, 16.8mmol, 1.05eq) dropwise at 0 °C. Stir the reaction mixture at 0 °C for 1 hour. LCMS analysis showed that the starting material had basically reacted completely, with a major new peak. Pour the reaction mixture into 30 mL of water, separate the layers, extract the aqueous phase once with 50 mL of ethyl acetate, wash the organic phase three times with saturated brine (50 mL), dry, evaporate to dryness, and separate by column chromatography to obtain 3-1 (3.6g, 91% yield) (colorless oil).

[0256]

[0257] (2) Add 3-1 (3.1 g, 13 mmol, 1.0 eq) to 30 mL of THF, then slowly add n-BuLi (6.42 mL, 2.5 M, 16 mmol, 1.2 eq) at -78 °C. Stir the reaction mixture at -78 °C for 0.5 hours, then slowly purge with CO2. After 10 min of purging, slowly bring the reaction mixture to room temperature. The product was detected by LCMS. Add 20 mL of water to the reaction mixture, separate the layers, and extract the aqueous phase once with 30 mL of ethyl acetate. Gradually adjust the pH of the aqueous phase to 4-5 with concentrated hydrochloric acid, filter, and dry to obtain 3-2 (3.2 g, 87% yield) (white solid).

[0258]

[0259] (3) 3-2 (3.1 g, 11 mmol, 1.0 eq), b (1.66 g, 16.8 mmol, 1.5 eq), and DMAP (0.13 g, 1.1 mmol, 0.1 eq) were added sequentially to 30 mL of pyridine. Then, SOCl2 (2.0 g, 16.8 mmol, 1.5 eq) was slowly added at 0 °C, and the reaction mixture was stirred at room temperature for 3 hours. The product was detected by LCMS. After concentrating to remove pyridine, 30 mL of water was added to the reaction mixture. The mixture was separated, and the aqueous phase was extracted three times with 30 mL of ethyl acetate. The organic phase was washed three times with saturated brine (50 mL). The mixture was dried, evaporated to dryness, and separated by column chromatography to obtain compound 3-3 (2.5 g, 63% yield) (white solid).

[0260]

[0261] (4) 3-3 (1 g, 2.8 mmol, 1.0 eq) and c (0.54 g, 3.1 mmol, 1.1 eq) were added sequentially to 10 mL of dichloromethane. The reaction mixture was then stirred at room temperature for 1 hour. The product was detected by LCMS, indicating that the reactants had essentially reacted. The reaction mixture was poured into 10 mL of water, quenched with sodium bisulfite, and separated. The aqueous phase was extracted three times with 30 mL of dichloromethane, and the organic phase was washed once with saturated brine (30 mL). The mixture was dried, evaporated to dryness, and separated by column chromatography to obtain the 3-racemic compound (0.85 g, 82% yield) (a grayish-white solid).

[0262]

[0263] (5) The 3-racemate of compound (0.5 g, 98% purity) was separated by chiral HPLC (Column: CHIRALPAK IG; Column Size: 3 cm x 25 cm, 5 μm; Injection: 3.0 ml; Mobile phase: Hex (0.2% FA): IPA = 50:50; Flow rate: 28 ml / min; Wavelength: UV 254 nm; Temperature: 25 °C; Sample solution: 70 mg / ml in EtOH / DCM; Run time = 60 mins) and concentrated. Single crystal diffraction confirmed that the white solid 3 (0.16 g, Rt = 10.51 min, 100% ee, purity 98%) and 3-S (0.13 g, Rt = 30.81 min, 99.8% ee, purity 96%) were obtained.

[0264]

[0265] 2. Synthesis of Compound 306

[0266] (1) Compound a was dissolved in 5 volumes of DMF solution, 1 equivalent of sodium hydroxide was added, the temperature was controlled at 5°C, and 1.05 equivalents of ethanethiol were added dropwise. The reaction was allowed to proceed for 2 hours. After the reaction was completed, 20 volumes of water were added, and the mixture was extracted twice with 5 volumes of methyl tert-butyl ether. The organic phases were combined and stirred dry, and purified by column chromatography to obtain product 306-1, with a yield of 93%.

[0267]

[0268] (2) Dissolve 306-1 in 10 volumes of tetrahydrofuran solution, maintain the temperature at -65°C under nitrogen protection, add 1.05 equivalents of n-butyllithium solution dropwise, and stir for 30 minutes. After purging with carbon dioxide gas for 5 minutes, the reaction is completed under central control. Add 5 volumes of water to quench the reaction. Remove the tetrahydrofuran solution under vacuum, extract once with ethyl acetate, adjust the pH of the aqueous phase to 2-3 with 1M hydrochloric acid, and a solid precipitates. Filter the solid, dry it, and obtain product 306-2 with a yield of 88%.

[0269]

[0270] (3) Dissolve 306-2 in 10 volumes of dichloromethane solution, add 1.1 equivalents of CDI, stir for 30 minutes, then add 1.05 equivalents of b and 1.05 equivalents of DBU, and stir at room temperature for 5 hours. After the intermediate control is completed, wash with 5 volumes of water, collect the organic phase, then wash with 5 volumes of 1M hydrochloric acid aqueous solution, collect the organic phase, dry it, and then evaporate to dryness to obtain product 306-3, with a yield of 80%.

[0271]

[0272] (4) Dissolve 306-3 in 5 volumes of DMF solution, add 3 equivalents of sodium methoxide solution, heat to 80°C, and react for 1 hour. After the reaction is completed, add 20 volumes of water, extract twice with 5 volumes of dichloromethane, evaporate the organic phase to dryness, and purify by reverse phase to obtain product 306-4, with a yield of 75%.

[0273]

[0274] (5) Dissolve 306-4 in 10 volumes of dichloromethane solution, add 1.0 equivalent of c, and stir at room temperature for 30 minutes. After the reaction is completed, quench the reaction with sodium bisulfite aqueous solution, remove the dichloromethane, and then purify by reverse phase to obtain the product 306-racemate, with a yield of 85%.

[0275]

[0276] (6) The racemic mixture of compound 306 (0.3 g, 95% purity) was separated by chiral HPLC (Column: CHIRALPAK IE; Column Size: 2 cm x 25 cm, 5 μm; Injection: 1.5 ml; Mobile phase: MtBE (0.2% FA): MeOH = 90:10; Flow rate: 20 ml / min; Wavelength: UV 254 nm; Temperature: 25 °C; Sample solution: 20 mg / ml in MeOH / DCM; Run time = 12 mins) and concentrated to obtain white solids 306-S (0.09 g, Rt = 6.02 min, 98.9% ee, purity 95%) and 306 (0.08 g, Rt = 8.87 min, 99.2% ee, purity 97%).

[0277]

[0278] 3. Synthesis of Compound 548

[0279] (1) Following the method described in section 2 above, compound 306-3 was synthesized. Then, 306-3 (10 g, 29 mmol, 1.0 eq) and m-CPBA (6.4 g, 31 mmol, 85% purity, 1.1 eq) were added sequentially to 200 mL of DCM. The reaction solution was then reacted at 0 °C for 0.5 hours. LC-MS analysis showed that the starting material disappeared and the main peak was the product. Excess oxides were quenched by adding saturated sodium bisulfite solution to the reaction solution. The solution was then concentrated, and the crude product was purified by column chromatography to obtain 548-1 (9.0 g, 86% yield) (white solid).

[0280]

[0281] (2) 548-1 (2.5 g, 6.8 mmol, 1.0 eq) and MeSNa (2.4 g, 34 mmol, 5.0 eq) were added to 40 ml of DMF, and the reaction solution was heated at 60 °C for 2 hours. LCMS showed that the starting material had basically reacted completely, and the main peak was the product. After filtration with a syringe, the product was purified by reverse-phase column chromatography. After concentrating the solvent and water, a white solid 548-racemate (1.2 g, 44.6% yield) was obtained (white solid).

[0282]

[0283] (3) The racemic 548 (0.5 g, 98% purity) was separated by chiral HPLC (Column: CHIRALPAK IG; Column Size: 3 cm x 25 cm, 5 μm; Injection: 3.0 ml; Mobile phase: Hex (0.2% FA): IPA = 50:50; Flowrate: 28 ml / min; Wavelength: UV 254 nm; Temperature: 25 °C; Sample solution: 70 mg / ml in EtOH / DCM; Run time = 60 mins) and concentrated to obtain white solids 548-S (0.21 g, Rt = 10.11 min, 100% ee, purity 98%) and 548 (0.18 g, Rt = 31.12 min, 99% ee, purity 96%).

[0284]

[0285] 4. Synthesis of Compound 637

[0286] (1) 637-1 (10 g, 70.4 mmol, 1.0 eq) was added to 100 mL of DCM, and then DAST (22.7 g, 140.8 mmol, 2 eq) was added dropwise to the reaction solution at 0 °C. After the addition was complete, the reaction solution was stirred at 20 °C for 16 hours. LCMS analysis showed that the starting material was almost completely consumed and a major new peak was formed. The reaction solution was poured into 100 mL of saturated NaHCO3 aqueous solution, extracted, and separated. The organic phase was washed three times with saturated brine (100 mL) and evaporated to dryness at low temperature. The crude product was purified by rapid column chromatography with petroleum ether, and after concentration, 637-2 (5 g, 43% yield) (colorless liquid) was obtained.

[0287]

[0288] (2) 637-2 (5 g, 30.5 mmol, 1.0 eq) and NaOH (1.34 g, 33.55 mmol, 1.1 eq) were added sequentially to 50 mL of DMF. Then, 637-3 (2.55 g, 33.55 mmol, 1.1 eq) was added dropwise to the reaction solution at 0 °C. After the addition was complete, the reaction solution was stirred at 0 °C for 3 hours. LCMS analysis showed that the starting material was almost completely consumed and a major new peak was formed. The reaction solution was poured into 50 mL of water, separated, and the aqueous phase was extracted once with 50 mL of ethyl acetate. The organic phase was washed three times with saturated brine (50 mL) and evaporated to dryness. The crude product was rapidly purified by column chromatography with petroleum ether and concentrated to obtain 637-4 (4 g, 60% yield) (colorless liquid).

[0289]

[0290] (3) 637-4 (4 g, 18.2 mmol, 1.0 eq) was added to 50 mL of THF. Then, n-BuLi (9.5 mL, 23.66 mmol, 1.3 eq) was added dropwise to the reaction solution at -78 °C. After the addition was complete, the reaction solution was stirred at -78 °C for 0.5 hours and then dry ice was gradually added. After the addition was complete, the reaction solution was gradually brought to room temperature. The product was detected by LCMS. The reaction solution was quenched in 50 mL of water, concentrated to remove THF, and then the aqueous phase was extracted once with ethyl acetate (50 mL). The pH was adjusted to 1-2 with concentrated hydrochloric acid. A solid precipitated and was filtered. After drying the filter cake, 637-5 (1.5 g, 31% yield) (yellow solid) was obtained.

[0291]

[0292] (4) 637-5 (1.5 g, 5.7 mmol, 1.0 eq) and CDI (1.1 g, 6.27 mmol, 1.1 eq) were added to 20 mL of DCM. The reaction solution was then reacted at 0 °C for 1 hour, followed by the sequential addition of DBU (0.95 g, 6.27 mmol, 1.1 eq) and b (0.627 g, 6.27 mmol, 1.1 eq). The reaction solution was gradually brought to room temperature and reacted for 8 hours. The product was detected by LCMS. The reaction solution was poured into 50 mL of water and extracted three times with dichloromethane (50 mL). The organic phase was then washed once with 4N hydrochloric acid (50 mL), dried over colorless sodium sulfate, concentrated, and purified by column chromatography to obtain 637-6 (1.2 g, 61% yield) (white solid).

[0293]

[0294] (5) 637-6 (1.2 g, 3.5 mmol, 1.0 eq) and m-CPBA (0.78 g, 3.85 mmol, 1.1 eq) were added sequentially to 20 mL of DCM. The reaction solution was then reacted at 0 °C for 0.5 hours. LC-MS analysis showed that the starting material disappeared and the main peak was the product. Excess oxides were quenched by adding saturated sodium bisulfite solution to the reaction solution, and then the solution was concentrated. After purification by column chromatography, 637-7 (0.7 g, 54% yield) (white solid) was obtained.

[0295]

[0296] (6) 637-6 (0.6 g, 1.7 mmol, 1.0 eq), H2O2 (1.97 g, 17.4 mmol, 10 eq), and catalyst I (CAS: 135620-04-1, 35 mg) were added sequentially to 10 mL of isopropanol. After reacting the solution at 0 °C for 12 hours, the product peak was detected by LCMS. Excess oxides were quenched by adding saturated sodium bisulfite solution to the reaction solution, and the solution was concentrated. After purification by column chromatography, the crude product was crystallized from ethyl acetate and ethanol to obtain 637 (0.15 g, 24% yield, ee = 95%, purity 95%) (white solid).

[0297]

[0298] Bioactivity evaluation:

[0299] The activity level standards for harmful plant damage (i.e., growth control rate) are as follows:

[0300] Level 5: Growth control rate is above 85%;

[0301] Level 4: Growth control rate is greater than or equal to 60% and less than 85%;

[0302] Level 3: Growth control rate greater than or equal to 40% and less than 60%;

[0303] Level 2: Growth control rate greater than or equal to 20% and less than 40%;

[0304] Level 1: Growth control rate greater than or equal to 5% and less than 20%;

[0305] Grade 0: Growth control rate is less than 5%.

[0306] The above growth control rates are fresh weight control rates.

[0307] Post-emergence testing experiment: Seeds of monocotyledonous and dicotyledonous weeds (such as shepherd's purse, cleavers, chickweed, barnyard grass, watercress, wild oats, purslane, hard grass, candle grass, wild oats, jointed barnyard grass, wild oats, amaranth, lambsquarters, dayflower, sow thistle, field bindweed, sow thistle, black nightshade, iron amaranth, crabgrass, barnyard grass, foxtail grass, golden foxtail grass, goosegrass, duckweed, arrowhead, firefly rush, nutgrass, sedge, sedge, purslane, purslane, cocklebur, morning glory) and seeds of major crops (wheat, Corn, rice, soybeans, cotton, rapeseed, millet, sorghum, potatoes, sesame, and castor beans were placed in plastic basins filled with soil, then covered with 0.5-2 cm of soil and allowed to grow in a favorable greenhouse environment. Two weeks after sowing, at the two-leaf stage, test plants were treated. The compound of this invention was dissolved in acetone, then Tween 80 was added, and methyl oleate emulsifiable concentrate at 1.5 L / ha was used as a synergist. The solution was diluted with water to a specific concentration and sprayed onto the plants using a spray tower. After application, the plants were incubated in a greenhouse for 15 days. After 15 days, the experimental effect on weeds was statistically analyzed. The compound dosages used were 500, 250, 125, 60, 30, and 15 g / ha, with three replicates, and the average value was taken. Representative data are listed in Table 3.

[0308] Table 3 Post-emergence weed test (active ingredient 250 g / ha)

[0309]

[0310]

[0311]

[0312]

[0313]

[0314]

[0315]

[0316]

[0317]

[0318]

[0319] Note: N represents untested.

[0320] Comparative experiment:

[0321] Unless otherwise specified, the post-emergence testing conditions are the same as above, and the experimental results are shown in Table 4-7.

[0322] Table 4. Results of the control experiment (weeds at 4-5 leaf stage 3-4 weeks after sowing, 25 DAA)

[0323]

[0324] Table 5. Results of the control experiment (3-4 weeks after sowing, direct-seeded rice variety Longyang 16 at 1.5-2 leaf stage, weeds at 4-5 leaf stage, 25 DAA)

[0325]

[0326]

[0327] Longyang 16 is a representative cultivar of important long-grain fragrant rice in Northeast China. Long-grain fragrant rice is relatively sensitive to herbicides, especially HPPD-type herbicides such as mesotrione and bicyclobutane, which easily cause phytotoxicity. Surprisingly, compound 3 (R configuration) showed higher safety in rice (Longyang 16) and better activity against key weeds such as *Echinochloa crus-galli*. In contrast, the control compound A (S configuration) was unsafe in rice, causing severe crop phytotoxicity, and showed even lower activity against key weeds, even lacking activity at low doses. This is inconsistent with the structure-activity relationship of well-known aryloxyphenoxypropionic acid herbicides, where the active form of phenoxypropionic acid herbicides exhibits high activity against weeds and severe crop phytotoxicity, while the inactive form shows almost no activity.

[0328] Furthermore, in this invention, for example, compounds 2,4,8,17,20,26,40,52,54,67,69,80,166,184,205,248,261,617,637, at dosages such as 125, 60, 30, and 15 g / ha, showed higher safety to crops such as rice compared to their corresponding racemic or S-configuration, and exhibited better activity against key weeds such as barnyardgrass and Echinochloa crus-galli. Moreover, when X is replaced by other five-membered rings, such as... At dosages such as 125, 60, 30, and 15 g / ha, compounds 379, 380, 382, ​​618, and 856 also exhibit superior herbicidal activity and / or crop safety compared to their racemic or S configurations.

[0329] Table 6 Results of the control experiment

[0330]

[0331]

[0332] Table 7. Results of the control experiment (16DAA)

[0333]

[0334]

[0335] Furthermore, in this invention, for example, compounds 549, 550, 552, 554, 559, 569, and 865, at dosages such as 120, 48, 30, and 24 g / ha, also exhibit superior herbicidal activity and / or crop safety compared to their corresponding racemic or S-configurations; for example, compounds 306, 308, 310, 311, 321, 348, 353, and 864 also exhibit superior herbicidal activity and / or crop safety compared to their corresponding racemic or S-configurations; and when X in the general formula is replaced by other five-membered rings such as... Z1 is replaced with methyl, Z2 with methanesulfonyl, or Y is replaced with... At the same time, they have the same or similar technical effects.

[0336] In summary, the herbicidal activity of the R-configuration compound of this application is significantly better than that of the racemic and S-configuration compounds, and it can maintain excellent crop safety.

[0337] Pre-seeding test experiment:

[0338] Seeds of monocotyledonous and dicotyledonous weeds, as well as seeds of major crops (wheat, corn, rice, soybean, cotton, rapeseed, millet, and sorghum), were placed in plastic basins filled with soil and covered with 0.5-2 cm of soil. The tested compounds of this invention were dissolved in acetone, then Tween 80 was added, and the solution was diluted with water to a specific concentration. The solutions were sprayed immediately after sowing. After application, the plants were incubated in a greenhouse for 4 weeks. Experimental results were observed after 3 weeks. It was found that most of the herbicides of this invention showed excellent efficacy at a dosage of 1000 g / ha, especially against barnyard grass, crabgrass, and velvetleaf, and many compounds exhibited good selectivity for corn, wheat, rice, soybeans, and rapeseed.

[0339] Through experiments, we found that the compounds described in this invention generally exhibit good weed control efficacy, especially against major grass weeds such as barnyard grass, crabgrass, and foxtail grass, which are prevalent in corn, rice, and wheat fields, as well as major broadleaf weeds such as velvetleaf, watercress, and beggar-ticks, demonstrating good commercial value. In particular, we noted extremely high activity against broadleaf weeds resistant to ALS inhibitors, such as watercress, shepherd's purse, shepherd's purse, cleavers, valerian, and chickweed.

[0340] Safety evaluation of transplanted rice and weed control efficacy evaluation in paddy fields:

[0341] After filling 1 / 1,000,000-hectare tanks with paddy field soil, sow seeds of barnyard grass, bulrush, wolfberry, wild arrowhead, duckweed, and purslane, and gently cover them with soil. Then, place the tanks in a greenhouse with water at a depth of 0.5-1 cm. The tubers of wild arrowhead are then planted the next day or two later. The water depth is maintained at 3-4 cm. When the barnyard grass, bulrush, wolfberry, duckweed, and purslane reach 0.5 leaves, and the wild arrowhead reaches the initial leaf stage, a water-diluted solution of the wettable powder or suspension of the compound of this invention, prepared according to conventional formulation methods, is evenly dripped using a pipette to achieve the specified effective ingredient concentration.

[0342] In addition, after filling the 1 / 1,000,000-hectare tank with paddy field soil, the soil is leveled to a water depth of 3-4 cm. The next day, 3-leaf stage rice (japonica / indica) is transplanted at a depth of 3 cm. The compound of the present invention is treated in the same way as described above on the 5th day after transplanting.

[0343] The growth status of barnyard grass, fireweed, wolfberry, goosegrass, arrowhead, and duckweed was observed with the naked eye on day 14 after treatment, and the growth status of rice was observed on day 21 after treatment. The herbicidal effect was evaluated using the above-mentioned activity standard level of 0-5. Many compounds showed excellent activity and selectivity.

[0344] Table 8. Herbicidal effect of the compounds (the dosage of the compounds in this application is 60 g / ha).

[0345]

[0346] Note: The seeds of barnyard grass, fireweed, wolfberry, wild arrowhead, and duck tongue grass were all collected from Heilongjiang, China. After testing, they showed resistance to conventional doses of pyrimisulfuron and penoxsulam.

[0347] This experiment demonstrates that the compound of the present invention exhibits excellent activity against weeds with ALS-inhibiting mechanisms that pose a serious challenge in production, and can solve the increasingly serious resistance problem.

[0348] Furthermore, numerous tests have revealed that the compounds and their compositions described in this invention exhibit excellent selectivity against many grassy lawns, including Zoysia japonica, Bermuda grass, tall fescue, Kentucky bluegrass, ryegrass, and seashore paspalum, effectively controlling many key grassy weeds as well as broadleaf weeds. Tests on wheat, corn, rice, sugarcane, soybeans, cotton, sunflowers, potatoes, fruit trees, and vegetables under different application methods also demonstrated excellent selectivity and commercial value.

Claims

1. An arylformamide compound containing a chiral sulfur oxide or a salt thereof, characterized in that, It is selected from any one of the following compounds: , 。 2. A method for preparing an arylformamide compound containing a chiral sulfur oxide as described in claim 1, characterized in that, Includes the following steps: (1) Using compounds as shown in general formula I' The compound represented by general formula I was obtained by liquid phase separation; or, (2) Using compounds as shown in general formula I'' Compounds of general formula I were prepared in the presence of peroxide and Jacobsen catalyst.

3. The method for preparing arylformamide compounds containing chiral sulfur oxides according to claim 2, characterized in that, In the reaction (2), the peroxide is H2O2; the reaction (2) is carried out in the presence of a solvent.

4. The method for preparing arylformamide compounds containing chiral sulfur oxides according to claim 3, characterized in that, The solvent is selected from at least one of methanol, ethanol, isopropanol, acetonitrile, dichloroethane, DMF, DMSO, dioxane, dichloromethane, or ethyl acetate.

5. A herbicidal composition, characterized in that, Includes (i) arylformamide compounds containing chiral sulfur oxides as described in claim 1, or their salts.

6. The herbicidal composition according to claim 5, characterized in that, It also includes (ii) one or more additional herbicides and / or safeners.

7. The herbicidal composition according to claim 5 or 6, characterized in that, It also includes (iii) agriculturally chemically acceptable formulation adjuvants.

8. A method for controlling weeds, characterized in that, This includes using an effective amount of at least one of the arylformamide compounds containing chiral sulfur oxides as described in claim 1 or a salt thereof, or the herbicidal composition as described in any one of claims 5-7, in a weedy area.

9. Use of at least one of the arylformamide compounds containing chiral sulfur oxides as described in claim 1 or a salt thereof, or the herbicidal composition as described in any one of claims 5-7, in weed control.

10. The use according to claim 9, characterized in that, The arylformamide compounds containing chiral sulfur oxides or their salts are used to control weeds in useful crops, wherein the useful crops are crops treated with genome editing technology.

Images