Chiral sulfur oxide-containing arylformamide compounds or salts thereof, preparation method, herbicidal compositions and their uses

Abstract

The present invention relates to the technical field of pesticides, and in particular to an arylformamide compound containing a chiral sulfur oxide or its salt, a preparation method, a herbicidal composition and its use. The arylformamide compound containing a chiral sulfur oxide or its salt has the following structural formula: [Formula 1] JPEG2022553987000168.jpg32165Z1 and Z2 each independently represent nitro, halogen, cyano, or the like; X is unsubstituted or substituted [Case 2] JPEG2022553987000169.jpg28165 Unsubstituted or substituted [C3] JPEG2022553987000170.jpg24165 Unsubstituted or substituted [C4] JPEG2022553987000171.jpg28165 Unsubstituted or substituted [C5] JPEG2022553987000172.jpg19166 Unsubstituted or substituted [C6] JPEG2022553987000173.jpg25166 Unsubstituted or substituted [C7] JPEG2022553987000174.jpg27166 Unsubstituted or substituted [C8] JPEG2022553987000175.jpg16165; Q represents halogen, cyano, cyanoalkyl, nitro, or the like; Y represents hydrogen, etc.; The compounds have the advantages of excellent herbicidal activity, higher crop safety, and excellent selectivity, especially against major crops such as wheat, rice, and corn.

Description

[Technical Field]

[0001] The present invention belongs to the field of agrochemicals, and more particularly to arylformamide compounds containing chiral sulfur oxides or their salts, methods for preparing them, herbicidal compositions, and their uses. [Background technology]

[0002] Weed inhibition and control are crucial steps in achieving highly efficient agricultural processes. A wide variety of herbicides are available on the market, and for example, WO2014086746A1, WO2016146561A1, WO2017144402A1, WO2012028579A1, etc., disclose specific arylcarboxamides and their use as herbicides. However, due to the continued expansion of the market, weed resistance, the lifespan of chemicals, and the economic efficiency of chemicals, and further due to the market's increasing focus on the serious emergence of resistance, particularly to mainstream herbicides (e.g., herbicides with ALS inhibitory mechanisms such as Penoxsulam, Bispyribac-sodium, and Nicosulfuron; herbicides with ACCe-based inhibitory mechanisms such as Cyhalofop-butyl, Clethodim, and Quizalofop-p-ethyl; and glyphosate), crops such as wheat, corn, rice, cotton, and soybeans face serious challenges, and there is a shortage of effective chemicals to control resistant weeds. Therefore, scientists are required to continuously research and develop new herbicides that are highly efficient, safe, and economical, with various modes of action.

[0003] Furthermore, many chiral herbicides have expanded into the market, including aryloxyphenoxypropionic acid herbicides such as quizalopop-p-ethyl, fluazifop-p-butyl, cyhalofop-butyl, metamihop, and phenoxaprop-p-ethyl, aryloxypropionic acid herbicides containing MCPA propionic acid and 2,4-D propionic acid, and chloroamide herbicides containing S-methrachlor. This expansion of chiral herbicides has significantly reduced the use of ineffective isomers and improved environmental safety. However, no sulfur-containing chiral herbicides are currently on the market. Surprisingly, this application discovers an arylcarboxamide compound, a sulfur-containing chiral herbicide, which is believed to have significant commercial value. [Overview of the Initiative]

[0004] According to the present invention, arylformamide compounds containing chiral sulfur oxides or their salts, methods for preparation, herbicidal compositions and their uses are provided, and these compounds have the advantages of excellent herbicidal activity, higher crop safety, and good selectivity for major crops in particular such as wheat, rice, and maize.

[0005] The technical solutions employed in this invention are as follows:

[0006] According to the present invention, an arylformamide compound or a salt thereof containing a chiral sulfur oxide having the following structural formula is provided: [ka] [In the formula, Z1 and Z2 are each independently halogen-containing or halogen-free groups selected from nitro, halogen, cyano, formyl, thiocyano, sulfhydryl, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, cycloalkylalkyl and cycloalkenylalkyl, 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 , -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 , -NR 4 R 5 , -NH-alkyl-NR 4 R 5 , -alkyl-OR1 ,-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 , [ka] P(O)(OR 6 )2, CH2P(O)(OR 6 )2, -SO2NR 4 R 5 -alkyl-S(O) m R 2 , represents -alkyl-CN, aryl, heteroaryl, heterocyclyl, arylalkyl, heteroarylalkyl or heterocyclylalkyl; R 1 , R 3 , R 4 and R 5 Each of these independently represents hydrogen, aryl, arylalkyl, heteroaryl, heteroarylalkyl, alkyl, alkyl halogenated, alkenyl, alkenyl halogenated, alkynyl, alkynyl halogenated, cycloalkyl, cycloalkyl halogenated, alkoxyalkyl, and cycloalkylalkyl, while the last 10 groups listed above represent cyano, halogen, nitro, thiocyano, OR 7 , S(O) m R 9 , NR 7 R 8 , NR 8 Ure 7 COR 7 , OCOR7 、SCOR 7 、NR 8 COR 7 、CO2R 7 、COSR 7 、CONR 7 R 8 and is substituted with an s group selected from the group consisting of alkoxyalkoxycarbonyl; R 2 independently represents aryl, arylalkyl, heteroaryl, heteroarylalkyl, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, and the last five groups each represent cyano, halogen, nitro, thiocyanato, 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 and is substituted with an s group selected from the group consisting of alkoxyalkoxycarbonyl; およびアルコキシアルコキシカルボニルからなる群から選択されるs基で置換されており; substituted with an s group selected from the group consisting of alkoxyalkoxycarbonyl; R 6 independently represents methyl or ethyl; R 7 and R 8 each independently represents hydrogen, alkyl, alkenyl or alkynyl; R 9 independently represents alkyl, alkenyl or alkynyl; X each represents unsubstituted or substituted

Chemical formula

[0007] Preferably, Z1 and Z2 are each independently halogen-containing or halogen-free groups selected from nitro, halogen, cyano, formyl, thiocyano, sulfhydryl, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkenyl, C3-C8 cycloalkyl-C1-C6 alkyl and C3-C8 cycloalkenyl-C1-C6 alkyl, OR 1 COR 1 COOR 1 , OCOR 1 OCOOR 1 , NR 3 SO2R 2OSO2R 2 , S(O) m R 2 , NR 3 COR 1 , NR 3 COOR 1 , C(O)NR 3 Ure 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 , [ka] P(O)(OR 6 )2, CH2P(O)(OR 6 )2, -SO2NR 4 R 5 -(C1-C6 alkyl)-S(O) m R 2 , represents -(C1-C6 alkyl)-CN, aryl, heteroaryl, heterocyclyl, aryl-C1-C6 alkyl, heteroaryl-C1-C6 alkyl or heterocyclyl-C1-C6 alkyl; R 1 , R 3 , R 4 and R 5Each of these 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 alkynyl, halogenated C2-C8 alkynyl, C3-C8 cycloalkyl, halogenated C3-C8 cycloalkyl, C1-C8 alkoxy-C1-C6 alkyl, and C3-C8 cycloalkyl-C1-C6 alkyl, and the last 10 groups above each represent cyano, halogen, nitro, thiocyano, OR 7 , S(O) m R 9 , NR 7 R 8 , NR 8 Ure 7 COR 7 , OCOR 7 SCOR 7 , NR 8 COR 7 CO2R 7 COSR 7 CONR 7 R 8 and are substituted with an s group selected from the group consisting of C1-C8 alkoxy-C1-C6 alkoxycarbonyl groups; R 2 These independently represent aryl, aryl-C1-C6 alkyl, heteroaryl, heteroaryl-C1-C6 alkyl, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, and C3-C8 cycloalkyl-C1-C6 alkyl, with the last five groups above representing cyano, halogen, nitro, thiocyano, and OR, respectively. 7 , S(O) m R 9 , NR 7 R 8 , NR 8 Ure 7 COR 7 , OCOR 7 SCOR 7 , NR 8 COR 7 CO2R 7 COSR 7 CONR 7 R8 and are substituted with an s group selected from the group consisting of C1-C8 alkoxy-C1-C6 alkoxycarbonyl groups; R 6 These independently represent methyl or ethyl; R 7 and R 8 Each of these independently represents hydrogen, a C1-C8 alkyl group, a C2-C8 alkenyl group, or a C2-C8 alkynyl group; R 9 These independently represent C1-C8 alkyl, C2-C8 alkenyl, or C2-C8 alkynyl; X is either unsubstituted or substituted. [ka] It represents; R 11 These are independently hydrogen, halogen, cyano, nitro, unsubstituted or R 13 Substituted C1-C8 alkyl, unsubstituted or R 14 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, represents heterocyclyl, heterocyclyl-C1-C6 alkyl, heterocyclyloxy, heterocyclylcarbonyl, aryl, aryl-C1-C6 alkyl, aryloxy, arylcarbonyl, heteroaryl, heteroaryl-C1-C6 alkyl, heteroaryloxy, heteroarylcarbonyl; R 12 These are independently hydrogen, unsubstituted or R 18 Represents C1-C8 alkyl, C3-C8 cycloalkyl, halogenated C3-C8 cycloalkyl, C2-C8 alkenyl, halogenated C2-C8 alkenyl, C2-C8 alkynyl, halogenated C2-C8 alkynyl, C3-C8 cycloalkenyl, or aryl substituted with; or M is R 11 and R 12 formed by [ka] If R is -(CH2)4- or -CH=CH-CH=CH-, 12 The nitrogen atom bonded to R 11 The bonded carbon atoms together form a six-membered ring; R 15 These are independent, non-substituted or R 21 This represents a C1-C8 alkyl group substituted with a substituent selected from C3-C8 cycloalkyl, halogenated C3-C8 cycloalkyl, C2-C8 alkenyl, halogenated C2-C8 alkenyl, C2-C8 alkynyl, halogenated C2-C8 alkynyl, C3-C8 cycloalkenyl, or phenyl; R 16 The terms independently represent C1-C8 alkyl, halogenated C1-C8 alkyl, C3-C8 cycloalkyl, C2-C8 alkenyl, halogenated C2-C8 alkenyl, C2-C8 alkynyl, halogenated C2-C8 alkynyl, or C3-C8 cycloalkenyl; R 21 These are independently halogens, cyano, C3-C8 cycloalkyl, hydroxy, sulfhydryl, C1-C8 alkoxy, and C(O)R 22carboxyl, C1-C8 alkoxycarbonyl, C1-C8 alkoxy-C1-C6 alkoxycarbonyl, -S(O) m C1-C8 alkyl, heteroaryl, heterocyclyl, or unsubstituted or R 23 Represents phenyl substituted with one or more (e.g., 1, 2, 3, 4, or 5) groups independently selected from; R 17 and R 22 Each of these is independently hydrogen, C1-C8 alkyl, or N(R) 24 )R 25 It represents; R 23 These are independently halogen, cyano, nitro, C1-C8 alkyl, unsubstituted or R 31 Substituted C1-C8 alkyl, C3-C8 cycloalkyl, halogenated C3-C8 cycloalkyl, C2-C8 alkenyl, halogenated C2-C8 alkenyl, C2-C8 alkynyl, halogenated C2-C8 alkynyl, C3-C8 cycloalkenyl, C1-C8 alkylcarbonyl, C3-C8 cycloalkylcarbonyl, halogenated C1-C8 alkylcarbonyl, halogenated C3-C8 cycloalkylcarbonyl, C1-C8 alkoxycarbonyl, halogenated C1-C8 alkoxycarbonyl, C1-C8 alkylaminocarbonyl, halogenated C1-C8 alkylaminocarbonyl, bis(C1-C8 alkyl)aminocarbonyl, OR 32 , S(O) m R 33 , represents C1-C8 alkylaminosulfonyl, bis(C1-C8 alkyl)aminosulfonyl, NH2, C1-C8 alkylamino, bis(C1-C8 alkyl)amino, aryl, heteroaryl, heterocyclyl; R 24 and R 25 Each of these independently represents hydrogen, a C1-C8 alkyl group, or a phenyl group; or R 24 and R 25 A C2-C8 alkylidene chain is formed by R 24 and R 25The bonded nitrogen atoms together form a 3-7 membered ring, and the C2-C8 alkylidene chain optionally contains one O, S, S(O), S(O)2, NH, or N-alkyl group, and is optionally substituted with an oxo group or a thio group; R 13 , R 14 , R 18 and R 31 These are, independently, halogen, cyano, nitro, carboxyl, C1-C8 alkoxycarbonyl, C1-C8 alkoxy-C1-C6 alkoxycarbonyl, and S(O) m R 41 , OR 42 , represents C1-C8 alkyl, halogenated C1-C8 alkyl, C2-C8 alkenyl, halogenated C2-C8 alkenyl, C2-C8 alkynyl, halogenated C2-C8 alkynyl, aryl, heteroaryl or heterocyclyl; R 32 The terms independently represent hydrogen, C1-C8 alkyl, halogenated C1-C8 alkyl, C3-C8 cycloalkyl, halogenated C3-C8 cycloalkyl, C2-C8 alkenyl, halogenated C2-C8 alkenyl, C2-C8 alkynyl, halogenated C2-C8 alkynyl, or C3-C8 cycloalkenyl; R 33 The terms independently represent C1-C8 alkyl, halogenated C1-C8 alkyl, C3-C8 cycloalkyl, C2-C8 alkenyl, halogenated C2-C8 alkenyl, C2-C8 alkynyl, halogenated C2-C8 alkynyl, or C3-C8 cycloalkenyl; R 41 and R 42 Each of these independently represents hydrogen, C1-C8 alkyl, halogenated C1-C8 alkyl, C3-C8 cycloalkyl, halogenated C3-C8 cycloalkyl, C2-C8 alkenyl, halogenated C2-C8 alkenyl, C2-C8 alkynyl, halogenated C2-C8 alkynyl, C3-C8 cycloalkenyl, phenyl, or benzyl; Q is a 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, 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 halogenated, cyano, C3-C8 cycloalkyl, C1-C8 alkylcarbonyl, C1-C8 alkoxycarbonyl, C1-C8 alkoxy, C1-C8 alkylsulfanyl, C1-C8 alkylsulfinyl, C1-C8 alkylsulfonyl or tri(C1-C8 alkyl)silyl, substituted with at least one group (e.g., 1 group, 2 groups, 3 groups, 4 groups, 5 groups) selected from C1-C8 alkyl, halogenated C1-C8 alkyl; unsubstituted or halogenated, cyano, C3-C8 cycloalkyl, C1-C8 alkylcarbonyl, C1-C8 alkoxy, C1-C8 alkylsulfanyl, C1-C8 alkylsulfinyl, or tri(C1-C8 alkyl)silyl. Represents a C2-C8 alkynyl group or C3-C8 cycloalkyl or C3-C8 cycloalkyl-C1-C6 alkyl group that is unsubstituted or substituted with at least one group selected from C1-C8 alkyl, halogen, or phenyl (e.g., one group, two groups, three groups, four groups, five groups); and represents an unsubstituted or substituted heterocyclyl, aryl, heteroaryl, heterocyclyl-C1-C6 alkyl, aryl-C1-C6 alkyl, or heteroaryl-C1-C6 alkyl group; Y is hydrogen, OR 54 , SR54 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 This represents halogen-free or halogen-containing C1-C8 alkyl, halogen-free or halogen-containing C2-C8 alkenyl, halogen-free or halogen-containing C2-C8 alkynyl, halogen-free or halogen-containing C3-C8 cycloalkyl, unsubstituted or substituted aryl-C1-C6 alkyl, or unsubstituted or substituted heteroaryl-C1-C6 alkyl; R 57 These are independently halogen-free or halogen-containing C2-C8 alkenyls, halogen-free or halogen-containing C2-C8 alkynyls, halogen-free or halogen-containing C3-C8 cycloalkyls, 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 or -O-(C=O)-N(R 63 ) represents 2; R 52 , R 54 and R 61Each of these independently represents hydrogen, halogen-free or halogen-containing C1-C8 alkyl, halogen-free or halogen-containing C2-C8 alkenyl, halogen-free or halogen-containing C2-C8 alkynyl, halogen-free or halogen-containing C3-C8 cycloalkyl, halogen-free or halogen-containing C3-C8 cycloalkyl-C1-C6 alkyl, halogen-free or halogen-containing C3-C8 cycloalkenyl, halogen-free or halogen-containing C1-C8 alkoxy-C1-C6 alkyl, unsubstituted or substituted heterocyclyl, unsubstituted or substituted heterocyclyl-C1-C6 alkyl, unsubstituted or substituted heterocyclyloxy-C1-C6 alkyl, unsubstituted or substituted aryl, unsubstituted or substituted aryl-C1-C6 alkyl, unsubstituted or substituted aryloxy-C1-C6 alkyl, unsubstituted or substituted heteroaryl, unsubstituted or substituted heteroaryl-C1-C6 alkyl, or unsubstituted or substituted heteroaryloxy-C1-C6 alkyl; R 53 and R 62 Each of these independently represents a halogen-free or halogen-containing C1-C8 alkyl, a halogen-free or halogen-containing C2-C8 alkenyl, a halogen-free or halogen-containing C2-C8 alkynyl, a halogen-free or halogen-containing C3-C8 cycloalkyl, a halogen-free or halogen-containing C3-C8 cycloalkyl-C1-C6 alkyl, a halogen-free or halogen-containing C3-C8 cycloalkenyl, a halogen-free or halogen-containing C1-C8 alkoxy-C1-C6 alkyl, an unsubstituted or substituted heterocyclyl, an unsubstituted or substituted heterocyclyl-C1-C6 alkyl, an unsubstituted or substituted aryl, an unsubstituted or substituted aryl-C1-C6 alkyl, an unsubstituted or substituted heteroaryl, or an unsubstituted or substituted heteroaryl-C1-C6 alkyl; R 51 , R 55 , R 56 , R 63 and R 64These are independently hydrogen, nitro, C1-C8 alkoxyaminocarbonyl, tri(C1-C8 alkyl)silyl, di(C1-C8 alkyl)phosphonyl, 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-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, arylcal Bonyl, arylsulfonyl, heteroaryl, heteroaryl-C1-C6 alkyl, heteroaryloxy, heteroaryloxy-C1-C6 alkyl, heteroaryl-C1-C6 alkyloxy, heteroarylcarbonyl, heteroarylsulfonyl, heterocyclyl, heterocyclyl-C1-C6 alkyl, heterocyclyloxy, heterocyclyloxy-C1-C6 alkyl, heterocyclyl-C1-C6 alkyloxy, heterocyclylcarbonyl, heterocyclylsulfonyl, -(C1-C6 alkyl)-NR 21 -aryl, -(C1-C6 alkyl)-NR 21 -heteroaryl or -(C1-C6 alkyl)-NR 21 - Represents heterocyclyl, and the last 35 groups above are each independently cyano, halogen, nitro, cyanothio, OR 71 , S(O) m R 72 , N(R 71 )2, NR 71 Ure 71 COR 71 , OCOR 71 SCOR 72 , NR71 COR 71 , NR 71 SO2R 72 CO2R 71 COSR 71 CON(R 71 ) Substituted with 0, 1, 2, or 3 groups selected from the group consisting of 2 and C1-C8 alkoxy-C1-C6 alkoxycarbonyl groups; R 71 These independently represent hydrogen, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, or C3-C8 cycloalkyl-C1-C6 alkyl; R 72 These independently represent C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, or C3-C8 cycloalkyl-C1-C6 alkyl; r represents 0, 1, or 2; m independently represents 0, 1, or 2; n independently represents either 0 or 1; 's' can independently represent 0, 1, 2, or 3.

[0008] More preferably, Z1 and Z2 are each independently a halogen-containing group or a halogen-free group selected from nitro, halogen, cyano, formyl, thiocyano, sulfhydryl, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkenyl, C3-C6 cycloalkyl-C1-C3 alkyl and C3-C6 cycloalkenyl-C1-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 Ure1 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)R 1 -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)-NR3 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 、

Chemical formula

[0009] More preferably, Z1 represents a halogen (e.g., fluorine or chlorine), cyano, C1-C6 alkyl (e.g., methyl), C1-C6 alkoxy (e.g., methoxy), C1-C6 alkoxy-C1-C6 alkoxy, C1-C6 alkoxy-C1-C6 alkylsulfanyl, or C1-C6 alkylsulfanyl (e.g., methylsulfanyl); Z2 represents a halogen, a C1-C6 alkyl, a halogenated C1-C6 alkyl (e.g., trifluoromethyl or difluoromethyl), or a C1-C6 alkylsulfonyl (e.g., methylsulfonyl); X is independent, [ka] It represents; R 11 '' independently represents hydrogen, C1-C6 alkyl, or C3-C6 cycloalkyl; R12 These independently represent hydrogen, C1-C6 alkyl, or C1-C6 alkoxy-C1-C3 alkyl; Q is independently cyano, cyanoC1-C3 alkyl, -(C1-C3 alkyl)-N(R 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 - Represents (C1-C6 alkyl), C1-C8 alkyl, halogenated C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, halogenated C2-C6 alkenyl, C3-C6 cycloalkyl-C1-C3 alkyl, unsubstituted or substituted heterocyclyl, unsubstituted or substituted heterocyclyl C1-C3 alkyl, unsubstituted or substituted heteroaryl-C1-C3 alkyl, or unsubstituted or substituted phenyl-C1-C3 alkyl; R 51 '' independently represents hydrogen or a C1-C6 alkyl group; R 52 '' independently represents hydrogen, C1-C6 alkyl, halogenated C1-C6 alkyl, phenyl-C1-C3 alkyl, or heteroaryl; Y independently represents hydrogen, C2-C6 alkynyl, C1-C6 alkylcarbonyl, heteroarylcarbonyl, C1-C6 alkoxycarbonyl, or -(C1-C3 alkyl)-O-(C=O)-O-(C1-C6 alkyl); r represents 0, 1, or 2; m represents 0, 1, or 2; The above heterocyclines [ka] Pointing to: The above heteroaryl is [ka] referring to; The above groups are either unsubstituted or substituted with at least one group selected from C1-C6 alkyl groups (e.g., one group, two groups, three groups, four groups, five groups); R' represents a C1-C6 alkyl group.

[0010] In another preferred embodiment of the present invention, Z1 represents a halogen, C1-C6 alkoxy, or C1-C6 alkylsulfanyl; Z2 represents C1-C6 alkyl, halogenated C1-C6 alkyl, or C1-C6 alkylsulfonyl; X is independent, each being either unsubstituted or substituted. [ka] It represents; R 11 These are independently hydrogen, halogen, cyano, NH2, unsubstituted or R 13 C1-C6 alkyl groups substituted with substituents selected from, unsubstituted or R 14 Represents C3-C6 cycloalkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 alkoxy, C1-C6 alkoxy, C1-C3 alkyl, or C1-C6 alkylcarbonylamino substituted with substituents selected from; R 12 These independently represent C1-C6 alkyl, C3-C6 cycloalkyl, C1-C6 alkoxy-C1-C3 alkyl, phenyl, or benzyloxy-C1-C3 alkyl; R 13 , R 14 Each of these independently represents a halogen, cyano, C1-C6 alkyl, or phenyl; Q is independently cyano, cyano C1-C3 alkyl, 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, 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-C6 alkyl, halogenated C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, halogenated C2-C6 alkenyl, halogenated C2-C6 alkynyl; unsubstituted or substituted with at least one group selected from C1-C6 alkyl, halogen, and phenyl, representing C3-C6 cycloalkyl or C3-C6 cycloalkyl-C1-C3 alkyl; unsubstituted or substituted heterocyclyl, phenyl, heteroaryl, heterocyclyl-C1-C3 alkyl, phenyl-C1-C3 alkyl, or heteroaryl-C1-C3 alkyl; R 51 '' independently represents hydrogen, C1-C6 alkyl, or halogenated C1-C6 alkyl; R 52 These independently represent hydrogen, halogen-free or halogen-containing C1-C6 alkyl, phenyl, phenyl-C1-C3 alkyl, or heteroaryl; Y independently represents hydrogen, halogen-free or halogen-containing C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, cyano-C1-C3 alkyl, C1-C6 alkylcarbonyl, benzyl, phenylcarbonyl, heterocyclylcarbonyl, heteroarylcarbonyl, C1-C6 alkyloxycarbonyl, or -(C1-C3 alkyl)-O-(C=O)-O-(C1-C6 alkyl); r represents 2; m represents 0, 1, or 2; The above "heterocycline" is [ka] The above "heteroaryl" refers to [ka] This refers to the above group, which is either unsubstituted or substituted with at least one group selected from C1-C6 alkyl groups; R' represents a C1-C6 alkyl group.

[0011] The R-configuration compound of the present invention is at position ( * The product has a stereochemical purity of 60-100%(R), preferably 70-100%(R), more preferably 80-100%(R), even more preferably 90-100%(R), and even more preferably 95-100%(R), relative to the content of stereoisomers having R and S configurations. Here, "stereochemical purity" refers to the percentage of the amount of the stereoisomers in the total amount of stereoisomers having chiral centers.

[0012] Furthermore, the salts are those commonly used in pesticides, such as metal salts, amine salts, sulfonium salts, and phosphonium salts. When these salts are used as herbicides for agricultural and horticultural purposes, they are also included in the present invention. In the present invention, the salts of the compounds are preferably in the form of alkali metal salts, alkaline earth metal salts, or ammonium salts (dimethylammonium salt, triethyl alcohol ammonium salt, isopropylamine salt, choline, etc.), preferably in the form of alkali metal salts, more preferably in the form of sodium salts or potassium salts, and most preferably in the form of sodium salts.

[0013] Solvates of the compounds of the present invention are also included in the present invention.

[0014] Herein, unless otherwise specified, the technical terms used in relation to the present invention, whether used alone or as part of a compound word, are not limited to "heterocyclyl," but include, for example, heterocyclyl having 0, 1, or 2 oxo groups. [ka] This includes; the “aryl” of the present invention is not limited to phenyl, naphthyl, [ka] This includes; "heteroaryl" can be an aromatic cyclic group having, for example, 3 to 6 (e.g., 3, 4, 5, or 6) ring atoms that can fuse with a benzo ring, and 1 to 4 (e.g., 1, 2, 3, or 4) ring heteroatoms selected from the group consisting of oxygen, nitrogen, and sulfur, for example [ka] The above groups are unsubstituted or halogen, nitro, amino, cyano, thiocyano, cyanoalkyl, sulfhydryl, hydroxy, hydroxyalkyl, carboxyl, formyl, trialkylsilyl, dialkylphosphonyl; unsubstituted or substituted heterocyclyl, heterocyclylalkyl, aryl, arylalkyl, heteroaryl or heteroarylalkyl; halogen-containing or halogen-free alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, cycloalkylalkyl, alkyl-substituted cycloalkyl, OR'', SR'', -alkyl-OR'', -O-alkyl-OR'', -alkyl-SR'', COR'', -alkyl-COR'', -O-alkyl-COR'', COOR'', -alkyl -COOR'', -O-alkyl-COOR'', COSR'', SOR'', SO2R'', -O-SO2R'', -alkyl-SO2R'', OCOR'', -alkyl-OCOR'' or SCOR'' groups; substituted with at least one (e.g., 1, 2, 3, 4, 5) amino, aminocarbonyl, aminocarbonylalkyl or aminosulfonyl groups, which are substituted with one or two groups selected from halogen-containing or halogen-free R'', COR'', SO2R'' or OR'' groups; or two adjacent substitutedable positions of the above "heterocyclyl", "aryl", or "heteroaryl" groups are linked by -OCH2CH2-, -OCH2O-, -OCH2CH2O- or -CH=CH-CH=CH- groups to form a ring; R'' independently represents alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl; unsubstituted or substituted heterocyclyl, heterocyclylalkyl, aryl, arylalkyl, heteroaryl, or heteroarylalkyl.

[0015] Preferably, the above groups are unsubstituted or halogen, nitro, amino, cyano, thiocyano, cyanoC1-C6 alkyl, sulfhydryl, hydroxy, hydroxyC1-C6 alkyl, carboxyl, formyl, tri(C1-C6 alkyl)silyl, di(C1-C6 alkyl)phosphonyl; unsubstituted or substituted heterocyclyl, heterocyclyl-C1-C6 alkyl, aryl, aryl-C1-C6 alkyl, heteroaryl , heteroaryl-C1-C6 alkyl; halogen-containing or halogen-free C1-C6 alkyl, 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'', COSR'', SOR' C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkenyl, C3-C6 cycloalkyl-C1-C6 alkyl, C3-C6 cycloalkyl; halogen-containing or halogen-free R'', COR'', SO2R'' ) substituted with one or two groups selected from OR'', or substituted with at least one group selected from amino, aminocarbonyl, aminocarbonyl-C1-C6 alkyl, or aminosulfonyl groups (e.g., 1, 2, 3, 4, or 5 groups); or two adjacent substituted positions of the above groups are linked by -OCH2CH2-, -OCH2O-, -OCH2CH2O-, or -CH=CH-CH=CH- groups to form a ring; R'' independently represents C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl-C1-C6 alkyl, C3-C6 cycloalkenyl; unsubstituted or substituted heterocyclyl, heterocyclyl-C1-C6 alkyl, aryl, aryl-C1-C6 alkyl, heteroaryl, heteroaryl-C1-C6 alkyl.

[0016] More preferably, the "heterocyclyl" has 0, 1, or 2 oxo groups. [ka] It refers to; "aryl" is, for example, phenyl, naphthyl, [ka] This refers to; "heteroaryl" is, for example, [ka] This refers to; the above groups are either unsubstituted or substituted with at least one group (e.g., 1, 2, 3, 4, or 5 groups) selected from halogen, nitro, amino, cyano, thiocyano, cyanoC1-C6 alkyl, sulfhydryl, hydroxy, hydroxyC1-C6 alkyl, carboxyl, or formyl; or unsubstituted or substituted with at least one group (e.g., 1, 2, 3, 4, or 5 groups) selected from halogen, hydroxy, nitro, cyano, amino, carboxyl, halogen-containing or halogen-free C1-C6 alkyl, halogen-containing or halogen-free C2-C6 alkenyl, halogen-containing or halogen-free C2-C6 alkynyl, halogen-containing or halogen-free C3-C6 cycloalkyl, halogen-containing or halogen-free C1-C6 alkoxy, halogen-containing or halogen-free C1-C6 alkoxycarbonyl, halogen-containing or halogen-free C1-C6 alkylacyl, halogen-containing or halogen-free C1-C6 alkylacyloxy, halogen-containing or halogen-free C1-C6 alkylamino, or halogen-containing or halogen-free C1-C6 alkylsulfonyl. [ka] Phenyl or benzyl group; halogen-containing or halogen-free C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl-C1-C6 alkyl, C3-C6 cycloalkyl substituted with C1-C6 alkyl, 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'', COSR'', SOR'', SO2R'' -O-SO2R'', -(C1-C6)alkyl-SO2R'', OCOR'', -(C1-C6)alkyl-OCOR'' or SCOR'' group; substituted with at least one (e.g., 1, 2, 3, 4, 5) amino, aminocarbonyl or aminosulfonyl groups substituted with one or two groups selected from halogen-containing or halogen-free R'', COR'', SO2R'' or OR''; or two adjacent substituted positions of the above "heterocyclyl", "aryl", or "heteroaryl" group are bonded to -OCH2CH2-, -OCH2O-, -OCH2CH2O- or -CH=CH-CH=CH- groups to form a ring; R' is independently hydrogen, nitro, hydroxy, amino; halogen-containing or halogen-free C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkenyl, C3-C6 cycloalkyl-C1-C6 alkyl, [ka] C1-C6 alkoxy, C2-C6 alkenyloxy, C2-C6 alkynyloxy, C3-C6 cycloalkyloxy, C1-C6 alkoxy-C1-C6 alkyl, C1-C6 alkoxycarbonyl, C1-C6 alkylsulfanylcarbonyl, C1-C6 alkylsulfonyl, C1-C6 alkylsulfonyl-C1-C6 alkyl, C1-C6 alkylcarbonyl, C1-C6 alkylcarbonylC1-C6 alkyl, C1-C6 alkylacyloxy, C1-C6 alkylamino, C1-C6 alkylaminocarbonyl, C1-C6 alkoxyaminocarbonyl, C1-C6 alkoxycarbonyl-C1-C6 alkyl, C1-C6 alkylaminocarbonyl-C1-C6 alkyl, tri(C1-C6 alkyl)silyl or di(C1-C6 alkyl)phosphonyl; unsubstituted Represents phenyl or benzyl substituted with at least one group (e.g., 1, 2, 3, 4, or 5 groups) selected from halogens, hydroxy, nitro, cyano, amino, carboxyl, halogen-containing or halogen-free C1-C6 alkylhalogens, halogen-containing or halogen-free C2-C6 alkenyls, halogen-containing or halogen-free C2-C6 alkynyls, halogen-containing or halogen-free C3-C6 cycloalkyls, halogen-containing or halogen-free C1-C6 alkoxys, halogen-containing or halogen-free C1-C6 alkoxycarbonyls, halogen-containing or halogen-free C1-C6 alkylacyls, halogen-containing or halogen-free C1-C6 alkylacyloxys, halogen-containing or halogen-free C1-C6 alkylaminos, or halogen-containing or halogen-free C1-C6 alkylsulfonyls; R'' independently includes C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl-C1-C6 alkyl, C3-C6 cycloalkenyl; and unsubstituted or halogen-containing or halogen-free C1-C6 alkyl, halogen-containing or halogen-free C2-C6 alkenyl, halogen-containing or halogen-free C2-C6 alkynyl, halogen-containing or halogen-free Substituted with at least one group (e.g., 1, 2, 3, 4, or 5 groups) selected from halogen-containing C3-C6 cycloalkyl, halogen-containing or halogen-free C1-C6 alkoxy, halogen-containing or halogen-free C1-C6 alkoxycarbonyl, halogen-containing or halogen-free C1-C6 alkylacyl, halogen-containing or halogen-free C1-C6 alkylacyloxy, halogen-containing or halogen-free C1-C6 alkylamino, or halogen-containing or halogen-free C1-C6 alkylsulfonyl. [ka] Represents phenyl or benzyl.

[0017] In the definitions of compounds represented by the above formula and all of the following structural formulas, the technical terms used, whether used alone or as part of a compound word, represent the following substituents: an alkyl group having three or more carbon atoms may be linear or branched. For example, the compound word "-alkyl-OR 1The alkyl group in " can be -CH2-, -CH2CH2-, -CH(CH3)-, -C(CH3)2-, etc. Alkyls include, 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, alkenyls include, for example, allyl, 1-methylprop-2-en-1-yl, 2-methylprop-2-en-1-yl, buto-2-en-1-yl, butyl-3-en-1-yl, 1-methylbuto-3-en-1-yl and 1-methylbuto-2-en-1-yl. Alkynnyls are, for example, propargyl, buto-2-in-1-yl, buto-3-in-1-yl, and 1-methylbuto-3-in-1-yl. At least one (e.g., 1, 2, or 3) multiple bonds can be present at any position on each unsaturated group. Cycloalkyls are carbocyclic saturated ring systems having 3 to 6 carbon atoms, such as cyclopropyl, cyclobutyl, cyclopentyl, or cyclohexyl. Similarly, cycloalkenyls are monocycloalkenyls having 3 to 6 carbon ring members, such as cyclopropenyl, cyclobutenyl, cyclopentenyl, and cyclohexenyl, where double bonds can be present at any position. Halogens are fluorine, chlorine, bromine, or iodine.

[0018] When a group is substituted with another group, this should be understood to mean that the group is substituted with one or more groups, which are identical or different groups selected from the group mentioned. Furthermore, the identical or different substitutional letters in the identical or different substituents are selected independently and may be identical or different. This also applies to ring systems formed with different atoms and units. On the other hand, compounds that are chemically unstable under standard conditions known to those skilled in the art are excluded from the claims.

[0019] Furthermore, unless otherwise specifically defined, the limiting markers in the parallel substituents of the present invention (separated by "," or "or"), such as "halogen-containing or halogen-free alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, cycloalkylalkyl or cycloalkenylalkyl," have a limiting effect on each substituent, and "halogen-containing or halogen-free" means that it has a limiting effect on each group "alkyl," "alkenyl," "alkynyl," "cycloalkyl," "cycloalkenyl," "cycloalkylalkyl," or "cycloalkenylalkyl"; "alkylamino" refers to an amino group that is monosubstituted or disubstituted with an alkyl group, and other substituted amino groups are defined similarly; groups whose bonding site is not specified (including heterocyclic, aryl, heteroaryl, etc.) can be bonded to any site including a C or N site; and if substituted, the substituent can be substituted at any site as long as it satisfies valence bond theory. For example, heteroaryl [ka] If it is substituted with one methyl group, [ka] These are possible.

[0020] Enantiomers can be obtained from mixtures prepared by conventional separation methods, such as chromatographic separation. Enantiomers can also be selectively prepared using stereoselective reactions with optically active starting materials and / or auxiliary materials.

[0021] In a particular embodiment, a method for preparing an arylformamide compound containing a chiral sulfur oxide or a salt thereof includes the following steps: (1) The compound of formula I, formula I' [ka] A process of obtaining the compound by liquid-phase separation (chiral HPLC separation, etc.); or (2) Compound I of formula I'' in the presence of a peroxide (H2O2, etc.) and a Jacobsen catalyst [ka] A process of preparing using [a specific method / tool].

[0022] Preferably, reaction (2) is carried out in the presence of a solvent; the solvent is at least one of methanol, ethanol, isopropanol, acetonitrile, dichloroethane, DMF, DMSO, dioxane, dichloromethane, or ethyl acetate.

[0023] The present invention provides a herbicide composition comprising (i) an arylformamide compound containing a chiral sulfur oxide or a salt thereof; preferably (ii) further comprising one or more additional herbicides and / or safety agents; and more preferably (iii) further comprising a pesticide-acceptable formulation aid.

[0024] The present invention provides a method for controlling weeds, comprising applying at least one arylformamide compound containing a chiral sulfur oxide or a salt thereof, or at least one herbicide composition, to a plant or weed area in an effective herbicidal amount.

[0025] The present invention provides the use of at least one arylformamide compound containing a chiral sulfur oxide or a salt thereof, or the above-mentioned herbicide composition, for the control of weeds, preferably the arylformamide compound containing a chiral sulfur oxide or a salt thereof, for inhibiting and / or controlling weeds of a useful crop, wherein the useful crop is a transgenic crop or a crop treated by gene editing technology.

[0026] The compounds of Formula I of the present invention have excellent herbicidal activity against a wide range of economically important monocotyledonous and dicotyledonous weeds. The active compounds also efficiently act on perennial weeds that are difficult to control, as they produce shoots from rhizomes, rootstocks, or other perennial organs. In this specification, it is not generally important whether the substance is applied before sowing, before germination, or after germination. Specifically, we can refer to several representative examples of monocotyledonous and dicotyledonous weed flora that can be controlled by the compounds of the present invention, without being limited to specific species. Examples of weed species in which the active compounds act efficiently include monocotyledonous species of the genera Avena, Lolium, Alopecurus, Phalaris, Echinochloa, Digitaria, and Setaria, as well as annual species of the genus Cyperus, and perennial species of Agropyron, Cynodon, Imperata, and Sorghum, as well as perennial species of Cyperus.

[0027] In the case of dicotyledonous weed species, the scope of its effects extends to, for example, annual plants such as Galium, Viola, Veronica, Lamium, Stellaria, Amaranthus, Sinapis, Ipomoea, Sida, Matricaria, and Abutilon, as well as perennial weeds such as Convolvulus, Cirsium, and Rumex. The active compounds of the present invention also have an effect on the excellent control of harmful plants that occur under certain rice cultivation conditions, such as Echinochloa, Sagittaria, Alisma, Eleocharis, Scirpus, and Cyperus. When the compounds of the present invention are applied to the soil surface before germination, the emergence of weed seedlings is completely inhibited, or the weeds grow until they reach the cotyledon stage, after which their growth stops, and they eventually die completely after 3-4 weeks. In particular, the compounds of the present invention exhibit excellent activity against Apera spica venti, Chenopodium album, Lamium purpureum, Polygonum convul ​​vulus, Stellaria media, Veronica hederifolia, Veronica persica, Viola tricolor, and the species of Amaranthus, Galium, and Kochia.

[0028] The compounds of the present invention have excellent herbicidal activity against monocotyledonous and dicotyledonous weeds, but cause little to no damage to economically important crop plants such as wheat, barley, rye, rice, maize, sugarcane, cotton, and soybeans. In particular, the compounds of the present invention have excellent compatibility with cereals such as wheat, barley, and maize, especially wheat. For these reasons, the compounds of the present invention are very suitable for selectively controlling the growth of undesirable plants in agricultural or ornamental plantings.

[0029] These active compounds can also be used to control harmful plants in crops of known or undeveloped genetically modified plants due to their herbicidal properties. Transgenic plants generally possess particularly advantageous properties, such as resistance to certain pesticides, especially certain herbicides, or resistance to plant diseases or pathogens, such as certain insects or fungi, bacteria, or viruses. Other specific properties relate to, for example, quantity, quality, storage stability, composition, and specific components of the harvested product. Thus, transgenic plants with increased starch content or altered starch quality, or transgenic plants with different fatty acid compositions in the harvested product are known.

[0030] The use of compounds of Formula I of the present invention or salts thereof is preferred in economically important transgenic crops of useful plants and ornamental plants, such as wheat, barley, rye, oats, millet, rice, cassava, and maize, or in crops of sugarcane, cotton, soybeans, rapeseed, potatoes, tomatoes, peas, and other vegetable species. Compounds of Formula I can preferably be used as herbicides in crops of useful plants that are resistant to the phytotoxic effects of herbicides or to which resistance has been conferred by genetic engineering.

[0031] Conventional methods for creating novel plants with modified characteristics compared to known plants include, for example, conventional breeding methods and the generation of mutants. Alternatively, novel plants with modified characteristics can be generated with the help of genetic engineering methods (see, for example, EP-A0221044 and EP-A0131624). For example, several cases are described: - Genetic modifications in crop plants to alter the starch synthesized by plants (see, for example, WO92 / 11376, WO92 / 14827, WO91 / 19806), - Transgenic crop plants resistant to certain glufosinate-type (see, e.g., EP-A0242236, EP-A0242246), glyphosate-type (WO92 / 00377), or sulfonylurea-type (EP-A0257993, U.S. Patent No. 5,013,659A) herbicides, - Transgenic crop plants capable of producing Bacillus thuringiensis toxin (Bt toxin) that confers resistance to specific pests to plants, such as cotton (EP-A0142924, EP-A0193259), - Transgenic crop plants with altered fatty acid composition (WO91 / 13972).

[0032] Many molecular biological techniques that enable the creation of novel transgenic plants with modified characteristics are known in principle; for example, Sambrook et al., 1989, Molecular Cloning, A Laboratory Manual, 2nd ed. Cold Spring Harbor Laboratory Press, Cold Spring Harbor, NY; or Winnacker “Gene und Klone” [Genes and Clones], VCH Weinheim, 2nd edition 1996; or Christou, “Trends in Plant Science” 1 (1996) 423-431). To perform such genetic engineering operations, it is possible to introduce nucleic acid molecules into plasmids that allow mutagenesis or sequence changes to occur through DNA sequence recombination. Using the standard processes described above, it is possible, for example, to substitute bases, delete partial sequences, or add natural or synthetic sequences. Adapters or linkers can be attached to DNA fragments to join them together.

[0033] Plant cells in which the activity of the gene product is reduced can be prepared, for example, by expressing at least one appropriate antisense RNA, a sense RNA to achieve a co-repression effect, or by expressing at least one appropriately constructed ribozyme that specifically cleaves the transcript of the gene product.

[0034] For this purpose, it is possible to use both DNA molecules containing the entire coding sequence of the gene product, including any potentially existing contiguous sequences, and DNA molecules containing only a portion of the coding sequence, provided that these portions are long enough to produce an antisense effect within the cell. It is also possible to use DNA sequences that have a high degree of homology to the coding sequence of the gene product, but are not completely identical.

[0035] When nucleic acid molecules are expressed in plants, the synthesized proteins can be localized to any desired compartment of the plant cell. However, to achieve localization in a specific compartment, it is possible, for example, to ligate a DNA sequence with a coding region that ensures localization in that specific compartment. Such sequences are known to those skilled in the art (see, for example, Braun et al., EMBO J. 11 (1992), 3219-3227; Wolter et al., Proc. Natl. Acad. Sci. USA 85 (1988), 846-850; Sonnewald et al., Plant J. 1 (1991), 95-106).

[0036] Transgenic plant cells can be regenerated into whole plants using known techniques. Transgenic plants can, in principle, be any desired plant species, i.e., both monocots and dicots. In this way, transgenic plants with modified characteristics can be obtained by overexpression, repression, or inhibition of homologous (=natural) genes or gene sequences, or by expression of heterologous (=foreign) genes or gene sequences.

[0037] When the active compounds of the present invention are used in transgenic crops, in addition to the effects on harmful plants that may be observed in other crops, effects specific to the application in each transgenic crop are frequently induced, such as alteration or particularly expansion of the spectrum of controllable weeds, changes in the amount that can be used for application, preferably good coherence with herbicides resistant to transgenic crops, and effects on the growth and yield of transgenic crop plants. Therefore, the present invention provides for the use of the compounds of the present invention as herbicides for controlling harmful plants in transgenic crop plants.

[0038] Furthermore, the substances of the present invention possess outstanding growth-regulating properties in crops. They are involved in plant metabolism in a regulatory manner and can be used for targeted control of plant components and to facilitate harvesting, for example, by inducing drought and growth inhibition. Moreover, they are also suitable for generally regulating and inhibiting undesirable vegetative growth without destroying the plant in the process. Since inhibition of vegetative growth can reduce or completely prevent lodging, inhibition of vegetative growth plays an important role in many monocots and dicots.

[0039] The compounds of the present invention can be applied to conventional formulations in the form of wetting powders, emulsifying concentrates, spray solutions, powders, or granules. Accordingly, the present invention provides herbicide compositions comprising the compound of formula I. The compound of formula I can be formulated in various ways depending on general biological and / or chemophysical parameters. Examples of suitable formulation options include: wetting powder (WP), water-soluble powder (SP), water-soluble concentrate, emulsifying concentrate (EC), emulsions (EW) such as oil-in-water and water-in-oil emulsions, spray solutions, suspension concentrates (SC), oil dispersions (OD), oily or aqueous dispersions, oil-miscible solutions, powders (DP), capsule suspensions (CS), seed dressing compositions, granules for spraying and soil application, microgranules, spray granules, coating granules and adsorbent granules, water-dispersible granules (WG), water-soluble granules (SG), etc., ULV formulations, microcapsules, and waxes. These individual formulation types are publicly known in principle and are described, for example, in Winnacker-Kuchler, “Chemische Technologie” [Chemical Technology], Volume 7, C. Hauser Verlag Munich, 4th Edition 1986; Wade van Valkenburg, “Pesticide Formulations”, Marcel Dekker, NY, 1973; and K. Martens, “Spray Drying” Handbook, 3rd Ed. 1979, G. Goodwin Ltd. London.

[0040] The use of necessary compounding aids such as inert materials, surfactants, solvents, and other additives is also an act, for example, Watkins, “Handbook of Insecticide Dust Diluents and Carriers”, 2nd Ed., Darland Books; Caldwell NJ, H. v. Olphen, “Introduction to Clay Colloid Chemistry”, 2nd Ed., J. Wiley & Sons, NY; C. Marsden, “Solvents Guide”, 2nd Ed., Interscience, NY 1963; McCutcheon's “Detergents and Emulsifiers Annual”, MC Publ. Corp., Ridgewood NJ; Sisley and Wood, “Encyclopedia of Surface Active Agents”, Chem. Publ. Co. Inc., NY 1964; Schonfeldt, “Grenzfluchenaktive Athylenoxidaddkte” [Surface-active ethylene oxide adducts], Wiss. This information is found in Verlagagesell. Stuttgart 1976; Winnacker-Kuchler, “Chemische Technologie” [Chemical Technology], Volume 7, C. Hauser Verlag Munich, 4th Edition 1986.

[0041] The wettable powder is a preparation that can be uniformly dispersed in water and contains, in addition to the active compound and diluent or inert substance, ionic and / or nonionic type surfactants (wetting agents, dispersants), such as polyethoxylated alkylphenols, polyethoxylated fatty alcohols, polyethoxylated fatty amines, fatty alcohol polyglycol ether sulfates, alkanesulfonates, alkylbenzene sulfonates, sodium ligninsulfonate, sodium 2,2'-dinaphthylmethane-6,6'-disulfonate, sodium dibutinaphthalenesulfonate, or sodium oleoylmethyltaurate. To prepare the wettable powder, the herbicidal active compound is finely ground using conventional equipment such as a hammer mill, fan mill, and air jet mill, and mixed simultaneously with or after the compounding aids.

[0042] Emulsifying concentrates are prepared by dissolving the active compound in an organic solvent, such as butanol, cyclohexanone, dimethylformamide, xylene, or other relatively high-boiling aromatic compounds or hydrocarbons or a mixture of solvents, along with the addition of one or more ionic and / or nonionic surfactants (emulsifiers). Examples of emulsifiers that can be used include calcium alkylaryl sulfonates such as calcium dodecylbenzenesulfonate, or nonionic emulsifiers such as fatty acid polyglycol esters, alkylaryl polyglycol ethers, fatty alcohol polyglycol ethers, propylene oxide-ethylene oxide condensate products, alkyl polyethers, sorbitan esters, such as sorbitan fatty acid esters or polyoxyethylene sorbitan esters, such as polyoxyethylene sorbitan fatty acid esters.

[0043] The powder is obtained by grinding the active compound together with a finely ground solid material such as talc, kaolin, bentonite, pyrophyllite, or diatomaceous earth. The suspension concentrate may be aqueous or oily. They can be prepared, for example, by wet grinding using a commercially conventional bead mill, with or without the addition of surfactants, as described above, in the case of other formulation types.

[0044] Emulsions, such as oil-in-water emulsions (EWs), can be prepared by a stirrer, colloidal mill, and / or static mixer, for example, in the case of other formulation types, using, for example, aqueous organic solvents and, if necessary, the surfactants described above.

[0045] Granules can be prepared by spraying the active compound onto an adsorbent granular inert material, or by coating the surface of a carrier such as sand, kaolinite, or granular inert material with an adhesive binder, such as polyvinyl alcohol, sodium polyacrylate, or other mineral oil. Suitable active compounds can also be granulated as a mixture with fertilizer, if necessary, by methods commonly used for the preparation of fertilizer granules. Water-dispersible granules are generally prepared by conventional processes such as spray drying, fluidized bed granulation, disc granulation, mixing with high-speed mixers, and extrusion without the use of solid inert materials.

[0046] For the preparation of discs, fluidized beds, extruders, and spray granules, see, for example, “Spray-Drying Handbook” 3rd ed. 1979, G. Goodwin Ltd., London; JE Browning, “Agglomeration”, Chemical and Engineering 1967, pages 147 ff.; “Perry's Chemical Engineer's Handbook”, 5th Ed., McGraw-Hill, New York 1973, pp. 8-57. For further details on the formulation of crop protection products, see, for example, GC Klingman, “Weed Control as a Science”, John Wiley and Sons Inc., New York, 1961, pages 81-96 and JD Freyer, SA Evans, “Weed Control Handbook”, 5th Ed., Blackwell Scientific Publications, Oxford, 1968, pages 101-103.

[0047] Pesticide formulations generally contain 0.1 to 99% by weight, particularly 0.1 to 95% by weight, of the active compound of formula I. In wet powders, the concentration of the active compound is, for example, about 10 to 99% by weight, with the remainder being 100% by weight of commonly used formulation components. In emulsified concentrates, the concentration of the active compound is about 1 to 90% by weight, preferably 5 to 80% by weight. Formulations in powder form contain 1 to 30% by weight of the active compound, preferably most commonly 5 to 20% by weight, while spray solutions contain about 0.05 to 80% by weight, preferably 2 to 50% by weight of the active compound. In the case of water-dispersible granules, the content of the active compound depends in part on whether the active compound is in liquid or solid form, and on the granulation aids, fillers, etc., used. In water-dispersible granules, the content of the active compound is, for example, 1 to 95% by weight, preferably 10 to 80% by weight.

[0048] Furthermore, the active compound formulation may include tackifiers, wetting agents, dispersants, emulsifiers, penetrants, preservatives, antifreezes, solvents, fillers, carriers, colorants, defoamers, evaporation inhibitors, and pH and viscosity modifiers, as commonly used in each case.

[0049] Based on these formulations, combinations with other pesticide-active substances, such as insecticides, acaricides, herbicides, and fungicides, as well as combinations with safety agents, fertilizers, and / or growth regulators, such as ready-mixes or tank mixes, can be manufactured.

[0050] Suitable active compounds that can be combined with the active compound of the present invention in mixed formulations or formulations for container mixing are, for example, known compounds described in the World Herbicide New Product Technology Handbook, China Agricultural Science and Farming Techniques Press, 2010.9 and the literature cited therein. For example, the following active compounds can be listed as herbicides that can be combined with the compound of formula I (Note: Compounds are named by their "common name" or chemical name by the International Organization for Standardization (ISO), along with a commonly used code number, where appropriate): acetochlor, butachlor, alachlor, propisochlor, metlachlor, s-metlachlor, pretilachlor, propachlor, etachlor, napropamide, R-left-handed napropamide Pamide, propanil, mefenacet, difenamide, diflufenican, etaprochlor, beflubutamide, bromobutide, dimethenamide, dimethenamide-P, etobenzanide, flufenacet, tenylchlor, metazachlor, isoxaben, flamprop-M-methyl, flamprop-M-propyl, alidocrol, petoxamide, chloranocryl, cyprazine, mefluidide, monalide, delacrol, prinachlor, te Lubuchlor, xylacrol, dimethachlor, cisanilide, trimexachlor, clomeprop, propizamide, pentanocrol, carbetamide, benzoylprop-ethyl, ciprazole, butenacrol, tebutam, benzipram, mogulton, diclofluanilide, naproanilide, dietatyl-ethyl, naptalam, flufenacet, benzadox, chlorthiamide, chlorophthalimide, isocarbamide, picolinafene Atrazine, Simazine, Promethrin, Cyanatrin, Simetrin, Ametrin, Propazine, Dipropetrin, SSH-108, Terbutrin, Terbutyrazine, Triaziflam, Ciprazine, Proglinadine, Trietadine, Prometon, Simeton, Adiprothrin, Desmethrin, Dimethametrin, Procyazin, Mesoprazine, Sebutyrazine, Sebumethrin, Terbumethrin, Metoprothrin, Cyanatrin, Ipazine, ChlorfazineAtlaton, pendimethalin, eglinadin, cyanuric acid, indadiflame, chlorsulfuron, metosulfuron-methyl, bensulfuron-methyl, chlorimulon-ethyl, tribeuron-methyl, thifensulfuron-methyl, pyrazosulfuron-ethyl, mesosulfuron, iodosulfuron-methylsodium, forumsulfuron, cinosulfuron, triasulfuron, sulfomethane-methyl, nicosulfuron, etamethosulfuron-methyl, amidesulfuron, ethoxysulfuron, cyclosulfamuron, limsulfuron, azimsulfuron Flazasulfuron, Monosulfuron, Monosulfuron-ester, Flucarbazone-sodium, Flupyrusulfuron-methyl, Halosulfuron-methyl, Oxasulfuron, Imazosulfuron, Primisulfuron, Propoxycarbazone, Prosulfuron, Sulfosulfuron, Trifloxysulfuron, Triflusulfuron-methyl, Tritosulfuron, Methosulfuron-methylsodium, Flucetosulfuron, HNPC-C, Orthosulfamuron, Propyrisulfuron, Metazosulfuron, Acifluorphen, Homesaphen, Lactofen, Flu Ologricofen, oxyfluorphen, chlornitrofen, acroniphen, ethoxyphen-ethyl, bifenox, nitrofluorphen, clomethoxyfen, fluorodiphen, fluoronitrofen, furyloxyfen, nitrofen, TOPE, DMNP, PPG1013, AKH-7088, halosaphen, chlortolurone, isoproturone, linulone, diuron, dimuron, fluomethurone, benzthiazurone, metabenzthiazurone, cumylon, ethidimuron, isouron, tebuthiuron, buturon, chlorbromurone, Methyl dimuron, phenobenzuron, SK-85, metobromulone, metoxron, afesin, monulone, sideuron, fenuron, fluothiurone, nevron, chloroxurone, norulone, isonorolone, 3-cyclooctyl-1, thiazflurone, tebuthiurone, diphenoxurone, paraflurone, methylaminetribnyl, carbchylate, trimethurone, dimeflon, monisourone, anislon, methirone, chloretulone, tetraflurone, fenmedifam, fenmedifam-ethyl, desmedifam, aslam, terbucarb,Burban, Profam, Chlorprofam, Lomate, Swep, Chlorbufam, Carboxazole, Chlorprocarb, Phenaslam, BCPC, CPPC, Carvaslam, Butyrate, Benchiocarb, Vernolate, Molinate, Trilate, Dimepiperate, Esprocarb, Pyributicarb, Cycloate, Avadex, EPTC, Ethiolate, Olbencarb, Peblate, Prosulfocarb, Thiocarbasil, CDEC, Dimexano, Isopolinate, Methiobencarb, 2,4-D-Butyl Ester, MCPA-Na, 2,4-D Isooctyl ester, MCPA isooctyl ester, 2,4-D sodium salt, 2,4-dimethylamine salt, MCPA-thioethyl, MCPA, 2,4-D propionic acid, high 2,4-D propionate, 2,4-D butyric acid, MCPA propionic acid, MCPA propionate, MCPA butyric acid, 2,4,5-D, 2,4,5-D propionic acid, 2,4,5-D butyric acid, MCPA amine salt, dicamba, ervon, chlorfenac, sezon, TBA, chloramben, methoxy-TBA, diclofop-methyl, fluadifop-butyl, fluadifop-p-butyl Haloxyfop-methyl, Haloxyfop-P, Quizalofop-ethyl, Quizalofop-p-ethyl, Phenoxaprop-ethyl, Phenoxaprop-p-ethyl, Propacizafop, Cyhalofop-butyl, Metamihop, Clodinafop-propargyl, Fentiaprop-ethyl, Chloroadifop-propynyl, Popenate-methyl, Triphopsim, Isoxapyrhop, Paraquat, Diquat, Oryzalin, Etalfluralin, Isoproparin, Nitralin, Profluralin, Prodinamin, Benfluralin, Fluchloralin, Di Nitramina, Diproparin, Chlornidine, Metalproparin, Dinoprop, Glyphosate, Anirofos, Glufosinate Ammonium, Amiprophos-Methyl, Sulfosate, Piperofos, Vialafos-Sodium, Benslide, Butamifos, Focarb, 2,4-DEP, H-9201, Zytron, Imazapyr, Imazetapir, Imazakine, Imazamox, Imazamox Ammonium Salt, Imazapick, Imazametabenz-Methyl, Fluroxypil, Fluroxypil Isooctyl Ester, Clopyralide, Pichloram, Triclopil, Dithiopil,Haloxydine, 3,5,6-trichloro-2-pyridinol, thiazopil, flulidone, aminopyralide, diflufenzopil, triclopil-butotyl, cliodinate, cethoxydime, cretoxydime, cycloxidime, alloxidime, crefoxydime, butroxidime, tralcoxidime, tepraloxidime, butidazole, metrivudine, hexazinone, metamitron, ethiodin, ametridione, amivudine, bromoxynil, bromoxynyl octanoate, ioxinyl octanoate, ioxinil, diclobenyl, diphenatril, py Laclonil, Chloroxynil, Iodobonyl, Flumezuram, Florasuram, Penoxuram, Methosuram, Chloransuram-methyl, Diclosuram, Pyroxyuram, Benfresate, Bispiribac-sodium, Pyribenzoxime, Pyriphthalide, Pyriminobac-methyl, Pyrithiobac-sodium, Benzobisilone, Mesotrione, Sulcotrione, Tempotrione, Tefuryltrione, Bicyclopyrone, Ketodopyradox, Isoxaflutol, Cromazon, Phenoxasulfone, Methiozoline, Fluazolate, Pyaflufen-ethyl Pyrazolinate, diphenzoquat, pyrazoxifen, benzofenap, nipiraclofen, pyrasulfol, topramesone, pyroxasulfone, caffenstrol, flupoxam, aminotriazole, amicarbazone, azaphenidine, carfentrazone-ethyl, sulfentrazone, bencarbazone, benzufenizone, butafenacil, bromacil, isocyl, lenacyl, terbacil, flupropacil, sinidone-ethyl, flumicrolac-pentyl, flumioxazine, propizamide, MK-129, flumazine, pentac Lolophenol, Dinoseb, Dinoterb, Dinoterb Acetate, Dinosam, DNOC, Chloronitrophen, Medinoterb Acetate, Dinophenate, Oxaziargyl, Oxadiazone, Pentoxazone, Flufenacet, Fluthiaset-methyl, Phentrazamide, Flufenpyr-ethyl, Pyrazone, Brompyrazone, Metoflurazone, Kusakira, Dimidazone, Oxapirazone, Norflurazone, Pyridafol, Quinclorac, Kinmelac, Bentazone, Piridate, Oxadiclomefone, Benazoline, Chromazon, Symmethilin,ZJ0702, pyribanebenzupropyl, indanophan, sodium chlorate, darapon, trichloroacetic acid, monochloroacetic acid, hexachloroacetone, flupropanate, cyperquat, bromophenoxime, epronaz, metasol, flurtamon, benfresate, etofmesate, thiochlorim, chlortal, fluorochloridone, taburon, acrolein, benthranil, tridiphan, chlorfenpropmethyl, tidiarizoimine, phenisophan, busoxynone, methoxyphenone, saflufenacil, clasifos, chloropon, allorac, dieatamquat, etonipromide, iprimidum, ibufencarbazone, thiencarbazone-methyl, pyrimisulfan, chlorflurazole, triphopindan, sulgulica Pin, Prosulfarin, Cambenziclor, Aminocyclopyracrol, Rodetanyl, Benoxacol, Fenchlorim, Flurazole, Fenchlorazole-ethyl, Croquintoceto-mexyl, Oxavethrinyl, MG / 9, Siometrinyl, DKA-24, Mefenpyr-diethyl, Frillazole, Fluxophenim, Isoxadifen-ethyl, Dichlormid, Ha Roxifen-methyl, DOW Florpyraxifene, UBH-509, D489, LS82-556, KPP-300, NC-324, NC-330, KH-218, DPX-N8189, SC-0744, DOWCO535, DK-8910, V-53482, PP-600, MBH-001, KIH-9201, ET-751, KIH-6127, and KIH-2023.

[0051] In this specification, where abbreviations for the general term of active compounds are used, they include, in each case, esters and salts, as well as isomers, in particular optical isomers, and especially one or more commercial forms. Where a general name indicates an ester or salt, it also includes, in each case, other esters and salts, free acids and neutral compounds, as well as isomers, in particular optical isomers, and especially one or more commercial forms. The chemical name given to a compound means at least one compound included in the general name, and generally preferred compounds. In the case of sulfamides such as sulfonylurea, the salts also include salts formed by exchanging a hydrogen atom with a cation of the sulfonamide group. For example, 2,4-D or 2,4-D butyrate derivatives include, but are limited to, salts of 2,4-D or 2,4-D butyrate such as sodium salt, potassium salt, dimethylammonium salt, triethanolammonium salt, isopropylamine salt, and choline salt, and esters of 2,4-D or 2,4-D butyrate such as methyl ester, ethyl ester, butyl ester, and isooctyl ester; MCPA derivatives include, but are not limited to, MCPA sodium salt, potassium salt, dimethylammonium salt, isopropylamine salt, and MCPA methyl ester, ethyl ester, isooctyl ester, and ethyl thioester.

[0052] For use, commercially available formulations are, where appropriate, diluted in a conventional manner, for example, with water in the case of wet powders, emulsified concentrates, dispersions, and water-dispersible granules. Products in the form of powders, soil application and spray granules, and spray solutions are not usually further diluted with other inert substances before use. The required amount of compound of formula I varies depending on external conditions such as temperature and humidity, and the properties of the herbicide used. It can vary within a wide range, for example, 0.001 to 1.0 kg / ha or more of the active substance, preferably 0.005 to 750 g / ha, and particularly 0.005 to 500 g / ha.

[0053] Specific forms for carrying out the present invention The following embodiments are used to illustrate the present invention in detail and should not be construed as any limitation to the invention. The scope of the invention is described through the claims.

[0054] Considering the economics, diversity, and biological activity of the compounds, the inventors have preferably synthesized several compounds, some of which are listed in Tables 1 and 2 below. The structures and information of specific compounds are shown in Tables 1 and 2. The compounds in Tables 1 and 2 are listed not for limiting purposes, but to further illustrate the invention. Those skilled in the art should not construed as limiting the subject matter of the invention to the following compounds. [Table 1] JPEG2022553987000032.jpg235166JPEG2022553987000033.jpg235166JPEG2022553987000034.jpg234165JPEG2022553987000035.jpg236166JPEG2022553987000036.jpg238166JPEG2022553987000037.jpg234165JPEG2022553987000038.jpg229166JPEG2022553987000039.jpg235166JPEG2022553987000040.jpg230166JPEG2022553987000041.jpg232166JPEG2022553987000042.jpg227166JPEG2022553987000043.jpg236166JPEG2022553987000044.jpg233165JPEG2022553987000045.jpg233166JPEG2022553987000046.jpg237165JPEG2022553987000047.jpg238166JPEG2022553987000048.jpg234166JPEG2022553987000049.jpg237165JPEG2022553987000050.jpg235165JPEG2022553987000051.jpg235166JPEG2022553987000052.jpg234166JPEG2022553987000053.jpg238166JPEG2022553987000054.jpg225165JPEG2022553987000055.jpg225166JPEG2022553987000056.jpg229166JPEG2022553987000057.jpg228166JPEG2022553987000058.jpg238165JPEG2022553987000059.jpg239166JPEG2022553987000060.jpg226165JPEG2022553987000061.jpg231165JPEG2022553987000062.jpg237165JPEG2022553987000063.jpg235165JPEG2022553987000064.jpg232166JPEG2022553987000065.jpg236166JPEG2022553987000066.jpg233165JPEG2022553987000067.jpg234165JPEG2022553987000068.jpg234166JPEG2022553987000069.jpg238166JPEG2022553987000070.jpg234165JPEG2022553987000071.jpg233166JPEG2022553987000072.jpg235166JPEG2022553987000073.jpg234166JPEG2022553987000074.jpg234166JPEG2022553987000075.jpg235165JPEG2022553987000076.jpg235166JPEG2022553987000077.jpg235165JPEG2022553987000078.jpg232165JPEG2022553987000079.jpg234165JPEG2022553987000080.jpg233166JPEG2022553987000081.jpg231166JPEG2022553987000082.jpg239165JPEG2022553987000083.jpg237166JPEG2022553987000084.jpg231166JPEG2022553987000085.jpg232166JPEG2022553987000086.jpg77166.

[0055]

Table 2

[0056] Methods for preparing the compounds of the present invention are described in detail in the following programs and embodiments. Materials are commercially available, reported in the literature, or prepared by known methods shown in the routes. Those skilled in the art should understand that the compounds of the present invention may also be synthesized by other synthetic routes. Details of the materials and reaction conditions in the synthetic routes are described in the following text, but can be readily substituted with other similar materials and conditions. For example, isomers of compounds produced by modifying the preparation methods of the present invention are included in the scope of the present invention. Furthermore, the preparation methods described below can be further modified in accordance with the disclosure of the present invention by using common chemical methods known to those skilled in the art, such as appropriate protection of groups in the reaction process.

[0057] The following application methods can be used to further understand the preparation methods of the present invention. Specific materials, classifications, and conditions are intended to further illustrate the present invention and are not intended to limit its reasonable scope. The reagents for the synthetic compounds listed in the table below can be purchased commercially or readily prepared by those skilled in the art.

[0058] Representative examples of compounds are listed below, and the synthesis methods for other compounds are similar, so they will not be explained in detail here.

[0059] 1. Synthesis of Compound 3 (1) Compound a (3 g, 16 mmol, 1.0 equivalent) and NaOH (0.72 g, 18 mmol, 1.1 equivalent) were sequentially added to 30 ml of DMF, and then compound n-PrSH (1.28 g, 16.8 mmol, 1.05 equivalent) was added dropwise at 0°C, and the reaction mixture was stirred at 0°C for 1 hour. LCMS analysis showed that the reaction of the starting materials was largely complete when a large new peak appeared. The reaction mixture was poured into 30 ml of water, the mixture was separated, the aqueous phase was extracted once with 50 ml of ethyl acetate, the resulting organic phase was washed three times with saturated brine (50 ml), dried, evaporated to dryness under reduced pressure, and separated by column chromatography to obtain compound 3-1 (3.6 g, yield 91%) (colorless oil). [ka]

[0060] (2) Compound 3-1 (3.1 g, 13 mmol, 1.0 equivalent) was added to 30 ml of THF, then n-BuLi (6.42 ml, 2.5 M, 16 mmol, 1.2 equivalents) was slowly added at -78°C, the reaction solution was stirred at -78°C for 0.5 hours, CO2 was slowly supplied for 10 minutes, and then the reaction solution was slowly warmed to room temperature. The product was detected by LC-MS. 20 ml of water was poured into the reaction solution to separate the mixture, the aqueous phase was extracted once with 30 ml of ethyl acetate, the obtained aqueous phase was gradually adjusted to pH=4~5 with concentrated hydrochloric acid, filtered, and dried to obtain compound 3-2 (3.2 g, yield 87%) (white solid). [ka]

[0061] (3) Compound 3-2 (3.1 g, 11 mmol, 1.0 equivalent), compound b (1.66 g, 16.8 mmol, 1.5 equivalents), and DMAP (0.13 g, 1.1 mmol, 0.1 equivalents) were sequentially added to 30 ml of pyridine. Then, SOCl2 (2.0 g, 16.8 mmol, 1.5 equivalents) was slowly added at 0°C, and the reaction solution was stirred at room temperature for 3 hours. The product was detected by LC-MS. Pyridine was concentrated and removed, and then 30 ml of water was added to the reaction solution to separate the mixture. The aqueous phase was extracted three times with 30 ml of ethyl acetate, and the resulting organic phase was washed three times with saturated brine (50 ml), dried, evaporated to dryness under reduced pressure, and separated by column chromatography to obtain compound 3-3 (2.5 g, yield 63%) (white solid). [ka]

[0062] (4) Compound 3-3 (1 g, 2.8 mmol, 1.0 equivalent) and compound c (0.54 g, 3.1 mmol, 1.1 equivalent) were successively added to 10 mL of dichloromethane. The reaction solution was then stirred at room temperature for 1 hour. The product was detected by LC-MS, indicating that the reaction of the materials was largely complete. The reaction solution was poured into 10 mL of water, the reaction was stopped with sodium bisulfite, and the mixture was separated. The aqueous phase was extracted three times with 30 mL of dichloromethane, the resulting organic phase was washed once with saturated brine (30 mL), dried, evaporated to dryness under reduced pressure, and separated by column chromatography to obtain compound 3-racemic compound (0.85 g, yield 82%) (grayish-white solid). [ka]

[0063] (5) Compound 3-racemic compound (0.5 g, purity 98%) was dissolved and separated by chiral HPLC (column: CHIRALPAK IG; column size: 3 cm × 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 min), then concentrated, and 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 determined by single crystal diffraction. [ka]

[0064] 2. Synthesis of Compound 306 (1) Compound a was dissolved in five times the volume of DMF solution, one equivalent of sodium hydroxide was added, the temperature was controlled to 5°C, and 1.05 equivalents of ethanethiol were added dropwise, and the mixture was reacted for 2 hours. After completing in-process control, 20 times the volume of water was added, and the mixture was extracted twice with five times the volume of methyl tert-butyl ether. The combined organic phase was dried under reduced pressure and purified by column chromatography to obtain product 306-1 in 93% yield. [ka]

[0065] (2) Product 306-1 was dissolved in 10 times the volume of tetrahydrofuran solution, the temperature was controlled to -65°C for nitrogen protection, 1.05 equivalents of n-butyllithium solution were added dropwise, and the mixture was stirred for 30 minutes. After 5 minutes of carbon dioxide gas injection, in-process quality control was completed and the reaction was stopped by adding 5 times the volume of water. The tetrahydrofuran solution was removed under vacuum and extracted once with ethyl acetate. The pH of the aqueous phase was adjusted to 2-3 with 1M hydrochloric acid, the solid was precipitated, filtered, and dried to obtain product 306-2 in 88% yield. [ka]

[0066] (3) Product 306-2 was dissolved in 10 times the volume of dichloromethane solution, and 1.1 equivalents of CDI were added; after stirring for 30 minutes, 1.05 equivalents of b and 1.05 equivalents of DBU were added, and the mixture was stirred at room temperature for 5 hours. After completing in-process quality control, the organic phase was recovered by washing with 5 times the volume of water, and then the organic phase was washed with 5 times the volume of 1 M hydrochloric acid aqueous solution, dried and concentrated under reduced pressure to obtain product 306-3 in 80% yield. [ka]

[0067] (4) Product 306-3 was dissolved in five times the volume of DMF solution, three equivalents of sodium methanol solution were added, the temperature was raised to 80°C, and the mixture was reacted for 1 hour. After completing in-process quality control, twenty times the volume of water was added, and the mixture was extracted twice with five times the volume of dichloromethane. The organic phase was dried under reduced pressure and purified by reverse-phase chromatography to obtain product 306-4 in 75% yield. [ka]

[0068] (5) Product 306-4 was dissolved in 10 times the volume of dichloromethane, 1.0 equivalent of C was added, and the mixture was stirred at room temperature for 30 minutes. After completing in-process quality control, the reaction was stopped using sodium bisulfite solution. After removing the dichloromethane, the reaction product was purified by reverse-phase chromatography to obtain product 306-racemic compound in 85% yield. [ka]

[0069] (6) Compound 306-racemic compound (0.3 g, 95% purity) was dissolved and separated by chiral HPLC (column: CHIRALPAK IE; column size: 2 cm × 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 min), and then concentrated to obtain white solids 306-S (0.09 g, Rt = 6.02 min, 98.9% ee, 95% purity) and 306 (0.08 g, Rt = 8.87 min, 99.2% ee, 97% purity). [ka]

[0070] 3. Synthesis of Compound 548 (1) Compound 306-3 was synthesized as described in (2) above. Compound 306-3 (10 g, 29 mmol, 1.0 equivalent) and m-CPBA (6.4 g, 31 mmol, 85% purity, 1.1 equivalent) were successively added to 200 ml of DCM, and the mixture was reacted at 0°C for 0.5 hours. Subsequently, LC-MS detection confirmed that the material had disappeared and the product was the main peak. Saturated sodium bisulfite solution was added to the reaction solution to suppress excess oxides, and the reactants were concentrated and separated by column chromatography to obtain product 548-1 (9.0 g, yield 86%) (white solid). [ka]

[0071] (2) Product 548-1 (2.5 g, 6.8 mmol, 1.0 equivalent) and MeSNa (2.4 g, 34 mmol, 5.0 equivalents) were added to 40 mL of DMF, and the reaction solution was heated at 60°C for 2 hours. LC-MS detection confirmed that the material was largely consumed and the main peak was the product. The product was filtered using a syringe, purified by reverse-phase column chromatography, and concentrated to obtain the white solid product 548-racemic compound (1.2 g, yield 44.6%) (white solid). [ka]

[0072] (3) The product 548-racemic mixture (0.5 g, 98% purity) was dissolved and separated by chiral HPLC (column: CHIRALPAK IG; column size: 3 cm × 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 min), and then concentrated white solids 548-S (0.21 g, Rt = 10.11 min, 100% ee, 98% purity) and 548 (0.18 g, Rt = 31.12 min, 99% ee, 96% purity) were obtained. [ka]

[0073] 4. Synthesis of Compound 637 (1) 637-1 (10 g, 70.4 mmol, 1.0 equivalent) was added to 100 ml of DCM, and then DAST (22.7 g, 140.8 mmol, 2 equivalents) was added dropwise to the reaction mixture at 0°C. After the addition was complete, the reaction mixture was stirred at 20°C for 16 hours. LC-MS detection confirmed that the material had been largely consumed and that a major new peak had appeared. The reaction mixture was poured into 100 ml of saturated NaHCO3 aqueous solution, and the reaction mixture was extracted and separated. The organic phase was washed three times with 100 ml of saturated brine and dried under low temperature and reduced pressure. The crude product was purified by column chromatography using petroleum ether as the eluent, and concentrated to obtain 637-2 (5 g, yield 43%) (colorless liquid). [ka]

[0074] (2) 637-2 (5 g, 30.5 mmol, 1.0 equivalent) and NaOH (1.34 g, 33.55 mmol, 1.1 equivalent) were continuously added to 50 ml of DMF, and then 637-3 (2.55 g, 33.55 mmol, 1.1 equivalent) was added dropwise to the reaction mixture at 0°C. After the addition was complete, the reaction mixture was stirred at 0°C for 3 hours. LC-MS detection confirmed that the material had been largely consumed and that a major new peak had appeared. The reaction mixture was poured into 50 ml of water, then 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 dried under reduced pressure. The crude product was purified by column chromatography using petroleum ether as the eluent, concentrated to obtain 637-4 (4 g, yield 60%) (colorless liquid). [ka]

[0075] (3) 637-4 (4 g, 18.2 mmol, 1.0 equivalent) was added to 50 ml of THF, and then n-BuLi (9.5 mL, 23.66 mmol, 1.3 equivalents) was added dropwise to the reaction mixture at -78°C. After addition, the reaction mixture was stirred at -78°C for 0.5 hours, and then solid dry ice was gradually added. After addition, the reaction solution was gradually warmed to room temperature. The presence of the product was confirmed by LC-MS detection. The reaction solution was poured into 50 ml of water to stop the reaction, and concentrated to remove THF. The aqueous phase was then extracted once with ethyl acetate (50 ml), the pH was adjusted to 1-2 with concentrated hydrochloric acid, the solid was precipitated and filtered, and the filter cake was dried to obtain 637-5 (1.5 g, yield 31%) (yellow solid). [ka]

[0076] (4) 637-5 (1.5 g, 5.7 mmol, 1.0 equivalent) and CDI (1.1 g, 6.27 mmol, 1.1 equivalent) were added to 20 ml of DCM. The reaction was carried out at 0°C for 1 hour, and then DBU (0.95 g, 6.27 mmol, 1.1 equivalent) and b (0.627 g, 6.27 mmol, 1.1 equivalent) were successively added to the reaction solution. The reaction solution was gradually warmed to room temperature and then carried out for 8 hours. The presence of the product was confirmed by LC-MS detection. 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 anhydrous sodium sulfate, concentrated, and purified by column chromatography to obtain 637-6 (1.2 g, yield 61%) (white solid). [ka]

[0077] (5) 637-6 (1.2 g, 3.5 mmol, 1.0 equivalent) and m-CPBA (0.78 g, 3.85 mmol, 1.1 equivalent) were continuously added to 20 ml of DCM. The reaction mixture was allowed to react at 0°C for 0.5 hours, and then LC-MS detection was performed to confirm that the material had disappeared and the product was the main peak. Saturated sodium bisulfite solution was added to the reaction solution to suppress excess oxides, and then the reaction solution was concentrated. The crude product was purified by column chromatography to obtain 637-7 (0.7 g, yield 54%) (white solid). [ka]

[0078] (6) 637-6 (0.6 g, 1.7 mmol, 1.0 equivalent), H2O2 (1.97 g, 17.4 mmol, 10 equivalents), and catalyst I (CAS: 135620-04-1, 35 mg) were sequentially added to 10 ml of isopropanol. The reaction mixture was allowed to react at 0°C for 12 hours, and then the appearance of the product peak was confirmed by LC-MS detection. Saturated sodium bisulfite solution was added to the reaction solution to suppress excess oxides, and then the reaction solution was concentrated. The crude product was purified by column chromatography and crystallized with ethyl acetate and ethanol to obtain 637 (0.15 g, yield 24%, ee=95%, purity 95%) (white solid). [ka]

[0079] Bioactivity assessment: The criteria for activity levels (i.e., growth control rates) related to damage to harmful plants are as follows: Level 5: Growth control rate exceeding 85%; Level 4: Growth control rate between 60% and 85%; Level 3: Growth control rate of 40% to less than 60%; Level 2: Growth control rate of 20% to less than 40%; Level 1: Growth control rate of 5% to less than 20%; Level 0: Growth control rate of less than 5%.

[0080] The growth control rate mentioned above is the fresh weight control rate.

[0081] Experiment on the weed control effect after germination: Monocotyledonous and dicotyledonous weed seeds (Descurainia sophia, Capsella bursa-pastoris, Galium aparine, Stellaria media, Lithospermum arvense, Rorippa indica, Alopecurus aequalis, Beckmannia syziga, Aegilops tauschii, Phalaris arundinacea, Amaranthus retroflexus, Chenopodiaceae, Commelina communis, Sonchus arvensis, Convolvulus) arvensis), Cirsium setosum, Solanum nigrum, Acalypha australis, Digitaria sanguinalis, Echinochloa crus, Scirpus juncoides, Cyperus rotundus, Cyperus iria, Cyperus difformis, Fimbristylis, Portulaca oleracea, Xanthium sibiricum, Pharbitis Seeds of major crops (wheat, corn, rice, soybeans, cotton, rapeseed, millet, sorghum, potato, and castor bean (ricinus)) were placed in plastic pots filled with soil, covered with 0.5-2 cm of soil, and grown in a good greenhouse environment. Two weeks after sowing, the test plants were treated at the two-leaf stage. Each test compound of the present invention was dissolved in acetone, and then Tween 80 and 1.5 liters / ha of emulsifiable methyl oleate concentrate were added as synergists. The solutions were diluted with a specific amount of water to obtain solutions of specific concentrations, which were then sprayed onto the plants using a spray tower.After application, plants were cultivated in a greenhouse for 15 days, and then the results of the weed control experiment were counted. The dosages of the compound used were 500, 250, 125, 60, 30, and 15 g / ha, and the average value was obtained by repeating the experiment three times. Representative data are shown in Table 3.

[0082] [Table 3] JPEG2022553987000125.jpg232169JPEG2022553987000126.jpg230168JPEG2022553987000127.jpg231169JPEG2022553987000128.jpg230169JPEG2022553987000129.jpg231169JPEG2022553987000130.jpg231169JPEG2022553987000131.jpg230169JPEG2022553987000132.jpg230168JPEG2022553987000133.jpg75169 Comparison experiment: In the absence of clear markers, the test conditions after seedling emergence are the same as described above, and the experimental results are shown in Tables 4-7.

[0083] [Table 4]

[0084] [Table 5]

[0085] Longyang16 is an important cultivar representing long-grain fragrant rice in northeastern China. Long-grain fragrant rice is sensitive to herbicides and is susceptible to damage from drugs, particularly HPPD herbicides such as mesotrione and benzobicilon. Surprisingly, compound 3 (R configuration) showed higher safety against rice (Longyang16) and superior activity against major weeds such as Leptocholus chinensis. However, control compound A (S configuration) was not safe for rice (i.e., caused significant crop damage), showed low activity against major weeds, and was inactive at low doses. The fact that effective forms of aryloxyphenoxypropionic acid herbicides and phenoxypropionic acid herbicides showed high activity against weeds and caused significant crop damage, while ineffective forms showed little activity, was inconsistent with well-known structure-activity correlations.

[0086] Furthermore, the present invention, for example, compounds 2, 4, 8, 17, 20, 26, 40, 52, 54, 67, 69, 80, 166, 184, 205, 248, 261, 617, and 637, showed higher safety to rice and other crops at doses of 125, 60, 30, and 15 g / ha compared to the corresponding racemic compounds or S configurations, and showed better activity against major weeds such as Digitaria sanguinalis and Leptochloa chinensis. [ka] When substituted with other five-membered rings, for example, compounds 379, 380, 382, ​​618, and 856 exhibited superior herbicidal activity and / or crop safety at doses of 125, 60, 30, and 15 g / ha compared to the corresponding racemic compounds or S configurations.

[0087] [Table 6]

[0088] [Table 7] JPEG2022553987000139.jpg221165

[0089] Furthermore, in the present invention, for example, compounds 549, 550, 552, 554, 559, 569, and 865 also have better herbicidal activity and / or crop safety at doses of 120, 48, 30, and 24 g / ha compared to the corresponding racemic compounds or S configurations; for example, compounds 306, 308, 310, 311, 321, 348, 353, and 864 have better herbicidal activity and / or crop safety compared to the corresponding racemic compounds or S configurations; X is [ka] Substituted with other 5-membered rings such as, Z1 is substituted with methyl, Z2 is substituted with methylsulfonyl, or Y is [ka] When replaced, it produces a similar or identical technical effect.

[0090] In conclusion, the R-configuration compound in this application clearly has superior herbicidal activity compared to racemic and S-configuration compounds, while maintaining good crop safety.

[0091] Experiment on the weed effect in the pre-germination stage: Seeds of monocotyledonous and dicotyledonous weeds and major crops (e.g., wheat, maize, rice, soybean, cotton, rapeseed, millet, and sorghum) were placed in plastic pots filled with soil and covered with 0.5-2 cm of soil. The test compounds of the present invention were dissolved in acetone, then Tween 80 was added, and the mixture was diluted with a specific amount of water to a specific concentration, which was then sprayed immediately after sowing. After spraying, the resulting seeds were cultivated in a greenhouse for 4 weeks, and the test results were observed after 3 weeks. The herbicides were observed to be highly effective against weeds, particularly Echinochloa crusgali, Digitaria sanguinalis, and Abutilon theophrasti, with the majority exhibiting excellent efficacy at an application rate of 1000 g / ha. In addition, many compounds showed good selectivity for maize, wheat, rice, soybean, rapeseed, etc.

[0092] This experiment demonstrated that the compounds of the present invention generally have good weed control effects and excellent commercial value against major grass weeds widely found in corn, rice, and wheat fields, particularly those such as Echinochloa crusgali, Digitaria sanguinalis, and Setaria viridis, as well as major broadleaf weeds such as Abutilon theophrasti, Rorippa indica, and Bidens pilosa. In particular, it should be noted that the compounds of the present invention exhibit very high activity against broadleaf weeds resistant to ALS inhibitors, such as Rorippa indica, Descurainia sophia, Capsella bursa-pastoris, Lithospermum arvense, Galium aparine, and Stellaria media.

[0093] Safety evaluation and weed control effectiveness evaluation of transplanted rice in paddy fields: Rice paddy soil was placed in pots measuring 1 / 1,000,000 hectares. Seeds of Echinochloa crusgali, Scirpus juncoides, Bidens tripartita, Sagittaria trifolia, Monochoria vaginalis, and Leptochloa chinensis were sown, gently covered with soil, and then left to stand in a greenhouse with a water level of 0.5-1 cm. Tubers of Sagittaria trifolia were planted the following day or two days later. After that, they were stored with a water level of 3-4 cm. The weeds were treated by uniformly dropping WP or SC aqueous dilutions, prepared according to a general preparation method for the compounds of the present invention, using a pipette. A predetermined effective dose was achieved when Echinochloa crusgali, Scirpus juncoides, Bidens tripartita, Monochoria vaginalis, and Leptochloa chinensis reached the 0.5-leaf stage, and when Sagittaria trifolia reached the primary leaf stage.

[0094] Furthermore, the soil from a paddy field placed in a pot representing 1 / 1,000,000 hectare was leveled, and water was maintained at a depth of 3-4 cm. The following day, rice plants (Japonica rice / Indica rice) at the 3-leaf stage were transplanted at a transplanting depth of 3 cm. Five days after transplanting, the compounds of the present invention were treated in the same manner.

[0095] The reproductive status of Echinochloa crusgali, Scirpus juncoides, Bidens tripartita, Leptochloa chinensis, Sagittaria trifolia, and Monochoria vaginalis was visually observed 14 days after treatment with the compounds of the present invention, as well as the reproductive status of rice 21 days after treatment with the compounds of the present invention. The weed control effect was evaluated on an activity level of 0 to 5. Many compounds showed excellent activity and selectivity.

[0096] [Table 8]

[0097] This experiment demonstrates that the compound of the present invention possesses an anti-ALS inhibitory mechanism, exhibits excellent activity against weeds, which pose a serious challenge in production, and therefore can solve the increasingly serious problem of resistance.

[0098] At the same time, the compounds and compositions of the present invention exhibit good selectivity for many grasses such as Zoysia japonica, Bermuda grass, Tall fescue, Bluegrass, Ryegrass, and Seashore Paspalum, and can control many important grass weeds and broadleaf weeds. These compounds also demonstrated excellent selectivity and commercial value in tests of various herbicide application methods on wheat, corn, rice, sugarcane, soybeans, cotton, oil sunflower, potatoes, fruit trees, and vegetables.

Claims

1. The following compounds: 8 to 9, 12 to 14, 29 to 33, 38, 40, 51, 165, 167, 169, 171, 176, 191 to 192, 196, 199, 203, 204, 206, 216, 223, 307 to 316, 318 to 341, 346 to 349, 351, 353 to 356, 379, 380, 382, ​​383, 428, 476 to 478, 481 to 486, 4 92-493, 496-501, 512-513, 515-518, 527, 529, 531-538, 543-564, 569-570, 573, 595-600, 602-612, 617-620, 622-628, 637, 856 and compounds 864-867, or salts thereof. 【Chemistry 1】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】

2. A method for preparing the chiral sulfur oxide-containing arylformamide compound or a salt thereof according to claim 1, comprising the steps of: (1) reacting a compound of formula I with a compound of formula I' 【Chemistry 31】 by liquid phase separation from a compound of formula (I); or (2) reacting a compound of formula I with a compound of formula I″ in the presence of peroxide and Jacobsen's catalyst. 【Chemistry 32】 The step of preparing [In formulae I′ and I″, groups X, Y, Z １ , Z ２ and Q are defined as in claim 1.

3. The peroxide in the reaction (2) is H ２ O ２ The method for preparing a chiral sulfur oxide-containing arylformamide compound or a salt thereof according to claim 2, wherein the reaction (2) is carried out in the presence of a solvent; and the solvent is at least one of methanol, ethanol, isopropanol, acetonitrile, dichloroethane, DMF, DMSO, dioxane, dichloromethane or ethyl acetate.

4. 13. A herbicidal composition comprising: (i) an arylformamide compound containing a chiral sulfur oxide according to claim 1 or a salt thereof; and (ii) one or more additional herbicides and / or safety agents.

5. 5. The herbicidal composition of claim 4, further comprising (iii) a pesticidally acceptable formulation adjuvant.

6. A method for controlling weeds, comprising applying to a plant or weed locus at least one of the chiral sulfur oxide-containing arylformamide compounds or salts thereof according to claim 1, or at least one of the herbicidal compositions according to claim 4 or 5, in a herbicidally effective amount.

7. 6. Use of at least one of the chiral sulfur oxide-containing arylformamide compounds or salts thereof according to claim 1, or the herbicidal composition according to claim 4 or 5, for controlling weeds.

8. 8. The use according to claim 7, wherein the chiral sulfur oxide-containing arylformamide compound or its salt is used for inhibiting and / or controlling weeds in useful crops, and the useful crops are transgenic crops or crops treated by gene editing technology.

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