Oxadiazolone compounds, herbicidal compositions and uses thereof

Abstract

The present application provides oxadiazolone compounds, herbicidal compositions, and uses thereof. The present application provides an oxadiazolone compound by substituting an oxadiazolone group represented by formula (a) at the position between the sulfonyl group and Cl on the benzene ring of a benzoyl compound, thereby obtaining an oxadiazolone compound. The oxadiazolone compound not only has unexpectedly high herbicidal activity against a variety of weeds, but is also relatively safe for a variety of crops, such as corn and rice. Experimental results have shown that the compound provided herein has relatively good herbicidal activity and can effectively control weeds, such as barnyard grass, crabgrass, and velvetleaf, at low doses, achieving good herbicidal efficacy while remaining relatively safe for crops.

Description

CROSS-REFERENCE TO RELATED APPLICATIONS

[0001] This application claims priority to a Chinese patent application filed on November 17, 2023, bearing application number 202311532732.0 and entitled "Oxadiazolone compounds, herbicidal compositions and uses thereof," the entire contents of which are incorporated herein by reference. [Technical Field]

[0002] The present application relates to the technical field of herbicides, and in particular to oxadiazolone compounds, herbicidal compositions and uses thereof. [Background technology]

[0003] Previous research has shown that benzoyl compounds have herbicidal activity, and that their herbicidal activity can be further improved by structural modification or alteration. However, compounds with high herbicidal activity have relatively low crop safety. Therefore, one of the current research trends in benzoyl herbicides is to obtain compounds that combine high herbicidal activity and high crop safety. Summary of the Invention [Problem to be solved by the invention]

[0004] In view of this, the technical problem to be solved by the present application is to provide an oxadiazolone compound, a composition containing the same, and uses thereof, and the oxadiazolone compound provided in the present application has high herbicidal activity and crop safety. [Means for solving the problem]

[0005] The present application provides an oxadiazolone compound represented by formula (I) or a tautomer thereof. [ka] In formula (I), R1 and R2 are independently selected from a C1-C6 alkyl group or a C3-C6 cycloalkyl group that is unsubstituted or substituted with 1 to 3 groups independently selected from a halogen, a nitro group, a C1-C6 alkyl group, a halogenated C1-C6 alkyl group, a C1-C6 alkoxy group, or a halogenated C1-C6 alkoxy group; Q is selected from the structures represented by Q1, Q2, or Q3; TIFF2025539307000002.tif25170 wherein A1, A2, A3, A4, and A5 are independently selected from O or S; R3 and R 10 are independently selected from hydrogen, an unsubstituted or halogen, a nitro group, a C1-C6 alkyl group substituted by 1 to 3 groups independently selected from a C1-C6 alkyl group, a halogenated C1-C6 alkyl group, a C1-C6 alkoxy group, a halogenated C1-C6 alkoxy group, a phenyl group, or a halogenated phenyl group, a C3-C6 cycloalkyl group, a C1-C6 alkoxy group, a phenyl group, or a benzyl group; n is an integer from 1 to 6, R4 is selected from hydrogen, halogen, unsubstituted or halogen, a nitro group, a C1-C6 alkyl group, a halogenated C1-C6 alkyl group, a C1-C6 alkoxy group, or a C1-C6 alkyl group substituted with 1 to 3 groups independently selected from halogen, a nitro group, a C1-C6 alkyl group, a halogenated C1-C6 alkyl group, a C1-C6 alkoxy group, or a halogenated C1-C6 alkoxy group, a C3-C6 cycloalkyl group, or a C1-C6 alkoxy group; R5 is selected from hydrogen, unsubstituted or halogen, a nitro group, a C1-C6 alkyl group, a halogenated C1-C6 alkyl group, a C1-C6 alkoxy group, and a C3-C6 cycloalkyl group substituted with 1 to 3 groups independently selected from halogen, a nitro group, a C1-C6 alkyl group, a halogenated C1-C6 alkyl group, a C1-C6 alkoxy group, and a halogenated C1-C6 alkoxy group; R6 is selected from hydrogen, a structure represented by formula (1), an unsubstituted or halogen-substituted C1-C6 alkyl group, a nitro group, a C1-C6 alkyl group, a halogenated C1-C6 alkyl group, a C1-C6 alkoxy group, or a C1-C6 alkoxy group, a C3-C6 cycloalkyl group, and a C3-C8 heterocyclic alkyl group; [ka] In formula (1), A6 is selected from N or CR9, and R9 is selected from hydrogen, an unsubstituted or halogen, a nitro group, a C1-C6 alkyl group, a halogenated C1-C6 alkyl group, a C1-C6 alkoxy group, or a halogenated C1-C6 alkoxy group, a C3-C6 cycloalkyl group, or a C1-C6 alkoxy group; R7 and R8 are independently selected from hydrogen, unsubstituted or halogen, a nitro group, a C1-C6 alkyl group, a halogenated C1-C6 alkyl group, a C1-C6 alkoxy group, or a C1-C6 alkyl group substituted with 1 to 3 groups independently selected from halogenated C1-C6 alkoxy groups, a C3-C6 cycloalkyl group, or a C1-C6 alkoxy group, and R7 and R8 are not simultaneously H; Alternatively, R7 and R8 together with A6 where they are located form a C3-C8 ring containing 0-3 heteroatoms, which is unsubstituted or substituted with 1-3 groups independently selected from a halogen, a nitro group, a C1-C6 alkyl group, a C3-C6 cycloalkyl group, a halogenated C1-C6 alkyl group, a C1-C6 alkoxy group, or a halogenated C1-C6 alkoxy group, and the heteroatoms are selected from oxygen, sulfur, or nitrogen.

[0006] The present applicant has discovered that oxadiazolone compounds obtained by substituting the group of formula (a) at the position between the sulfonyl group and Cl on the benzene ring of a benzoyl compound not only have excellent herbicidal activity against a variety of weeds, but are also relatively safe for a variety of crops such as corn and rice. [ka]

[0007] In some specific implementations, in formula (I), R1 and R2 are independently selected from a C1-C4 alkyl group or a C3-C6 cycloalkyl group that are unsubstituted or substituted with 1 to 3 groups independently selected from a halogen, a nitro group, a C1-C4 alkyl group, a halogenated C1-C4 alkyl group, a C1-C4 alkoxy group, or a halogenated C1-C4 alkoxy group; in some specific implementations, R1 and R2 are independently selected from -CH3, -CH2CH3, -CH2CH2CH3, -CH(CH3)2, - In some specific implementations, R1 is selected from a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, or a tert-butyl group; and R2 is selected from a methyl group, an ethyl group, an n-propyl group, a tert-butyl group, or a trifluoromethyl group.

[0008] In some specific implementations, Q is selected from the structure denoted by Q1, TIFF2025539307000005.tif22170 where A1 and A2 are independently selected from O or S. In some specific implementations, A1 and A2 are both O.

[0009] In the Q1 structure, R3 is preferably selected from hydrogen, unsubstituted or halogen, nitro, C1-C4 alkyl, halogenated C1-C4 alkyl, C1-C4 alkoxy, halogenated C1-C4 alkoxy, phenyl, or halogenated phenyl, C3-C6 cycloalkyl, C1-C4 alkoxy, phenyl, or benzyl; in some specific embodiments, R3 is selected from hydrogen, C1-C4 alkyl, phenyl, or benzyl; in some specific embodiments, R3 is selected from hydrogen, methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, tert-butyl, phenyl, p-chlorophenyl, 2,4-dichlorophenyl, benzyl, p-chlorobenzyl, or 2,4-dichlorobenzyl.

[0010] In the Q1 structure, n is the number of substituents R3 and is an integer of 1 to 6, and may be 1, 2, 3, 4, 5, or 6, and is preferably 1, 2, or 3.

[0011] In some specific implementations, Q is selected from the structure shown in Q2, In the TIFF2025539307000006.tif20170Q2 structure, A3 is selected from O or S. In some specific implementations, A3 is O.

[0012] In the Q2 structure, R4 is preferably selected from hydrogen, halogen, unsubstituted or substituted with 1 to 3 groups independently selected from halogen, nitro, C1-C4 alkyl, halogenated C1-C4 alkyl, C1-C4 alkoxy, or halogenated C1-C4 alkoxy, C3-C6 cycloalkyl, or C1-C4 alkoxy. In some specific implementations, R4 is selected from hydrogen, halogen, C1-C4 alkyl, halogenated C1-C4 alkyl, C3-C6 cycloalkyl, or C1-C4 alkoxy. In some specific implementations, R4 is selected from hydrogen, chlorine, C1-C4 alkyl, or C3-C6 cycloalkyl. In some specific implementations, R4 is selected from hydrogen, methyl, ethyl, isopropyl, or cyclopropyl.

[0013] In the Q2 structure, R5 is preferably selected from hydrogen, a C1-C4 alkyl group or a C3-C6 cycloalkyl group that is unsubstituted or substituted with 1 to 3 groups independently selected from a halogen, a nitro group, a C1-C4 alkyl group, a halogenated C1-C4 alkyl group, a C1-C4 alkoxy group, or a halogenated C1-C4 alkoxy group; in some specific implementations, R5 is selected from hydrogen, a C1-C4 alkyl group, a halogenated C1-C4 alkyl group, or a C3-C6 cycloalkyl group; in some specific implementations, R5 is selected from a methyl group, an ethyl group, or a cyclopropyl group.

[0014] In the Q2 structure, R6 is preferably selected from hydrogen, the structure represented by formula (1), a C1-C4 alkyl group unsubstituted or substituted with 1 to 3 groups independently selected from halogen, a nitro group, a C1-C4 alkyl group, a halogenated C1-C4 alkyl group, a C1-C4 alkoxy group, or a halogenated C1-C4 alkoxy group, a C3-C6 cycloalkyl group, or a C3-C8 heterocyclic alkyl group; and in some specific implementations, R6 is selected from hydrogen, the structure represented by formula (1), a C1-C4 alkyl group, a C3-C6 cycloalkyl group, a C3-C8 heterocyclic alkyl group, or a halogenated C1-C4 alkyl group. [ka]

[0015] In formula (1), A6 is selected from N or CR9, and R9 is selected from hydrogen, unsubstituted or substituted with 1 to 3 groups independently selected from halogen, nitro, C1-C6 alkyl, halogenated C1-C6 alkyl, C1-C6 alkoxy, or halogenated C1-C6 alkoxy, C3-C6 cycloalkyl, or C1-C6 alkoxy. In some specific implementations, R9 is selected from hydrogen, C1-C4 alkyl, C3-C6 cycloalkyl, C1-C4 alkoxy, halogenated C1-C4 alkyl, or halogenated C1-C4 alkoxy. In some specific implementations, R9 is selected from methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, or tert-butyl.

[0016] In formula (1), R7 and R8 are independently selected from hydrogen, unsubstituted or halogen, nitro, C1-C6 alkyl, halogenated C1-C6 alkyl, C1-C6 alkoxy, or halogenated C1-C6 alkoxy; C3-C6 cycloalkyl, or C1-C6 alkoxy; and in some specific implementations, R7 and R8 are independently selected from hydrogen, C1-C4 alkyl, C3-C6 cycloalkyl, C1-C4 alkoxy, halogenated C1-C4 alkyl, or halogenated C1-C4 alkoxy. In some specific implementations, R7 and R8 are independently selected from methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, or tert-butoxy. In formula (1), R7 and R8 are not simultaneously H.

[0017] In formula (1), R7 and R8 preferably form a C3-C8 ring containing one to three heteroatoms, unsubstituted or substituted with one to three groups independently selected from halogen, nitro, C1-C4 alkyl, C3-C6 cycloalkyl, halogenated C1-C4 alkyl, C1-C4 alkoxy, or halogenated C1-C4 alkoxy, where the heteroatoms are selected from oxygen, sulfur, or nitrogen. In some specific embodiments, R7 and R8 preferably form a heterocycle, unsubstituted or substituted with one to three groups independently selected from halogen, nitro, C1-C4 alkyl, C3-C6 cycloalkyl, halogenated C1-C4 alkyl, C1-C4 alkoxy, or halogenated C1-C4 alkoxy, selected from a pyrazole ring, a furan ring, a tetrahydrofuran ring, a thiophene ring, or a tetrahydrothiophene ring, where the heteroatoms are selected from oxygen, sulfur, or nitrogen. In some specific embodiments, R7 and R8 preferably form a ring with A6 where they are located, as shown in the following structure: TIFF2025539307000008.tif35170 where R1 , R 3 , R 4 , R 6 are independently selected from hydrogen, halogen, a C1-C4 alkyl group, a halogenated C1-C4 alkyl group, or a C3-C6 cycloalkyl group, and are preferably selected from hydrogen, chlorine, a trifluoromethyl group, a methyl group, an ethyl group, an isopropyl group, or a cyclopropyl group. 2 , R 5 , R 7 are independently selected from hydrogen, a C1-C4 alkyl group, a halogenated C1-C4 alkyl group, or a C3-C6 cycloalkyl group, and preferably selected from hydrogen, a methyl group, an ethyl group, or a cyclopropyl group.

[0018] In some specific implementations, R6 is preferably selected from the following structures: TIFF2025539307000009.tif50170

[0019] where R 1 , R 3 , R 4 , R 6 are independently selected from hydrogen, halogen, a C1-C4 alkyl group, a halogenated C1-C4 alkyl group, or a C3-C6 cycloalkyl group, and are preferably selected from hydrogen, chlorine, a trifluoromethyl group, a methyl group, an ethyl group, an isopropyl group, or a cyclopropyl group. 2 , R 5 , R 7 are independently selected from hydrogen, a C1-C4 alkyl group, a halogenated C1-C4 alkyl group, or a C3-C6 cycloalkyl group, and preferably selected from hydrogen, a methyl group, an ethyl group, or a cyclopropyl group.

[0020] In some specific implementations, Q is selected from the structure shown in Q3, In the TIFF2025539307000010.tif18170Q3 structure, A4 and A5 are independently selected from O or S; in some specific implementations, A4 is selected from O and A5 is selected from O or S.

[0021] In the Q3 structure, R 10 is preferably selected from hydrogen, unsubstituted or halogen, nitro group, C1-C4 alkyl group, halogenated C1-C4 alkyl group, C1-C4 alkoxy group, halogenated C1-C4 alkoxy group, phenyl group or halogenated phenyl group, C3-C6 cycloalkyl group, C1-C4 alkoxy group, phenyl group or benzyl group, and in some specific implementations, R 10 is selected from hydrogen, a C1-C4 alkyl group, a phenyl group unsubstituted or substituted with 1-3 halogens, or a benzyl group unsubstituted or substituted with 1-3 halogens, and in some specific implementations, R 10 is selected from hydrogen, methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, tert-butyl, phenyl, p-chlorophenyl, 2,4-dichlorophenyl, benzyl, p-chlorobenzyl, or 2,4-dichlorobenzyl. 10 is selected from H, -CH3, -CH2CH3, -CH2CH2CH3, -CH(CH3)2, -C(CH3)3, -CH2CH2CH2CH3, a phenyl group, a chlorophenyl group, a dichlorophenyl group, C6H5CH2-, C6H4ClCH2- or C6H3Cl2CH2-.

[0022] In some specific implementations, Q is selected from the structure shown as Q1-1, TIFF2025539307000011.tif22170R3 is selected from H, a C1 to C4 alkyl group, or a C1 to C4 halogenated alkyl group.

[0023] In some specific implementations, Q is selected from the structure shown in Q3-1, TIFF2025539307000012.tif18170R 10is selected from H, a C1 to C4 alkyl group, a C1 to C4 halogenated alkyl group, a phenyl group, a halogenated phenyl group, a C1 to C4 alkyl group substituted with a phenyl group, or a C1 to C4 alkyl group substituted with a halogenated phenyl group.

[0024] In some specific implementations, Q is selected from the structure shown in Q2-1, TIFF2025539307000013.tif22170X1 is selected from C or N, X2 is selected from C, N, O or S, and X1 and X2 are not both C, R 11 is selected from H, halogen, a C1-C4 alkyl group, a C3-C6 cycloalkyl group, or a C1-C4 halogenated alkyl group, and in some specific implementations, R 11 are H, CH3, CF3, -CH2CH 3、 It is selected from a cyclopropyl group or Cl. m is a substituent R 11 is an integer between 1 and 3, R4 is selected from hydrogen, halogen, C1-C4 alkyl groups, halogenated C1-C4 alkyl groups, C3-C6 cycloalkyl groups, halogenated C3-C6 cycloalkyl groups, C1-C4 alkoxy groups, and halogenated C1-C4 alkoxy groups; R5 is selected from hydrogen, a C1-C4 alkyl group or a halogenated C1-C4 alkyl group.

[0025] In some specific implementations, the compound is selected from the following compounds: Compound 1: Q is selected from the structure represented by Q1-1, R1=CH3, R2=CH3, R3=H, Compound 2: Q is selected from the structure represented by Q1-1, R1 = CH3, R2 = CH2CH3, R3 = H, Compound 3: Q is selected from the structure represented by Q1-1, R1 = CH3, R2 = CH2CH2CH3, R3 = H, Compound 4: Q is selected from the structure represented by Q1-1, R1 = CH3, R2 = C(CH3)3, R3 = H, Compound 5: Q is selected from the structure represented by Q1-1, R1=CH3, R2=CF3, R3=H, Compound 6: Q is selected from the structure represented by Q1-1, R1 = CH2CH3, R2 = CH3, R3 = H, Compound 7: Q is selected from the structure represented by Q1-1, R1 = CH2CH3, R2 = CH2CH3, R3 = H, Compound 8: Q is selected from the structure represented by Q1-1, R1 = CH2CH3, R2 = CH2CH2CH3, R3 = H, Compound 9: Q is selected from the structure represented by Q1-1, R1 = CH2CH3, R2 = C(CH3)3, R3 = H, Compound 10: Q is selected from the structure represented by Q1-1, R1 = CH2CH3, R2 = CF3, R3 = H, Compound 11: Q is selected from the structure represented by Q1-1, R1 = CH2CH2CH3, R2 = CH3, R3 = H, Compound 12: Q is selected from the structure represented by Q1-1, R1 = CH2CH2CH3, R2 = CH2CH3, R3 = H, Compound 13: Q is selected from the structure represented by Q1-1, R1 = CH2CH2CH3, R2 = CH2CH2CH3, R3 = H, Compound 14: Q is selected from the structure represented by Q1-1, R1 = CH2CH2CH3, R2 = C(CH3)3, R3 = H, Compound 15: Q is selected from the structure represented by Q1-1, R1 = CH2CH2CH3, R2 = CF3, R3 = H, Compound 16: Q is selected from the structure represented by Q1-1, R1 = CH(CH3)2, R2 = CH3, R3 = H, Compound 17: Q is selected from the structure represented by Q1-1, R1 = CH(CH3)2, R2 = CH2CH3, R3 = H, Compound 18: Q is selected from the structure represented by Q1-1, R1 = CH(CH3)2, R2 = CH2CH2CH3, R3 = H, Compound 19: Q is selected from the structure represented by Q1-1, R1 = CH(CH3)2, R2 = C(CH3)3, R3 = H, Compound 20: Q is selected from the structure represented by Q1-1, R1 = CH(CH3)2, R2 = CF3, R3 = H, Compound 21: Q is selected from the structure represented by Q1-1, R1 = CH2CH2CH2CH3, R2 = CH3, R3 = H, Compound 22: Q is selected from the structure represented by Q1-1, R1 = CH2CH2CH2CH3, R2 = CH2CH3, R3 = H, Compound 23: Q is selected from the structure represented by Q1-1, R1 = CH2CH2CH2CH3, R2 = CH2CH2CH3, R3 = H, Compound 24: Q is selected from the structure represented by Q1-1, R1 = CH2CH2CH2CH3, R2 = C(CH3)3, R3 = H, Compound 25: Q is selected from the structure represented by Q1-1, R1 = CH2CH2CH2CH3, R2 = CF3, R3 = H, Compound 26: Q is selected from the structure represented by Q1-1, R1 = C(CH3)3, R2 = CH3, R3 = H, Compound 27: Q is selected from the structure represented by Q1-1, R1 = C(CH3)3, R2 = CH2CH3, R3 = H, Compound 28: Q is selected from the structure represented by Q1-1, R1 = C(CH3)3, R2 = CH2CH2CH3, R3 = H, Compound 29: Q is selected from the structure represented by Q1-1, R1 = C(CH3)3, R2 = C(CH3)3, R3 = H, Compound 30: Q is selected from the structure represented by Q1-1, R1 = C(CH3)3, R2 = CF3, R3 = H, Compound 31: Q is selected from the structure represented by Q3, R1=CH3, R2=CH3, A4=O, A5=O, R 10 =CH3, Compound 32: Q is selected from the structure represented by Q3, R1=CH3, R2=CH3, A4=O, A5=O, R 10 =CH2CH3, Compound 33: Q is selected from the structure represented by Q3, R1=CH3, R2=CH3, A4=O, A5=O, R 10 =CH2CH2CH3, Compound 34: Q is selected from the structure represented by Q3, R1=CH3, R2=CH3, A4=O, A5=O, R 10 =CH(CH3)2, Compound 35: Q is selected from the structure represented by Q3, R1=CH3, R2=CH3, A4=O, A5=O, R 10 =CH2CH2CH2CH3, Compound 36: Q is selected from the structure represented by Q3, R1=CH3, R2=CH3, A4=O, A5=O, R 10 =C(CH3)3, Compound 37: Q is selected from the structure represented by Q3, R1=CH3, R2=CH3, A4=O, A5=O, R 10 = TIFF2025539307000014.tif12170, Compound 38: Q is selected from the structure represented by Q3, R1=CH3, R2=CH3, A4=O, A5=O, R 10 = TIFF2025539307000015.tif13170, Compound 39: Q is selected from the structure represented by Q3, R1=CH3, R2=CH3, A4=O, A5=O, R 10 = TIFF2025539307000016.tif18170, Compound 40: Q is selected from the structure represented by Q3, R1=CH3, R2=CH3, A4=O, A5=O, R 10 = TIFF2025539307000017.tif14170, Compound 41: Q is selected from the structure represented by Q3, R1=CH3, R2=CH3, A4=O, A5=O, R 10 = TIFF2025539307000018.tif15170, Compound 42: Q is selected from the structure represented by Q3, R1=CH3, R2=CH3, A4=O, A5=O, R 10 = TIFF2025539307000019.tif18170, Compound 43: Q is selected from the structure represented by Q3, R1=CH3, R2=CH3, A4=O, A5=O, R 10 = TIFF2025539307000020.tif11170, Compound 44: Q is selected from the structure represented by Q3, R1 = CH3, R2 = CH3, A4 = O, A5 = S, R 10 =CH3, Compound 45: Q is selected from the structure represented by Q3, R1 = CH3, R2 = CH3, A4 = O, A5 = S, R 10 =CH2CH3, Compound 46: Q is selected from the structure represented by Q3, R1 = CH3, R2 = CH3, A4 = O, A5 = S, R 10 =CH2CH2CH3, Compound 47: Q is selected from the structure represented by Q3, R1 = CH3, R2 = CH3, A4 = O, A5 = S, R 10 =CH(CH3)2, Compound 48: Q is selected from the structure represented by Q3, R1 = CH3, R2 = CH3, A4 = O, A5 = S, R 10 =CH2CH2CH2CH3, Compound 49: Q is selected from the structure represented by Q3, R1 = CH3, R2 = CH3, A4 = O, A5 = S, R 10 =C(CH3)3, Compound 50: Q is selected from the structure represented by Q3, R1 = CH3, R2 = CH3, A4 = O, A5 = S, R 10 = TIFF2025539307000021.tif12170, Compound 51: Q is selected from the structure represented by Q3, R1 = CH3, R2 = CH3, A4 = O, A5 = S, R 10 = TIFF2025539307000022.tif13170, Compound 52: Q is selected from the structure represented by Q3, R1 = CH3, R2 = CH3, A4 = O, A5 = S, R 10 = TIFF2025539307000023.tif18170, Compound 53: Q is selected from the structure represented by Q3, R1 = CH3, R2 = CH3, A4 = O, A5 = S, R 10 = TIFF2025539307000024.tif14170, Compound 54: Q is selected from the structure represented by Q3, R1 = CH3, R2 = CH3, A4 = O, A5 = S, R 10 = TIFF2025539307000025.tif15170, Compound 55: Q is selected from the structure represented by Q3, R1 = CH3, R2 = CH3, A4 = O, A5 = S, R 10 = TIFF2025539307000026.tif18170, Compound 56: Q is selected from the structure represented by Q2, A3=O, R1=CH3, R2=CH3, R4=H, R5=CH3, R6=H, Compound 57: Q is selected from the structure represented by Q2, A3=O, R1=CH3, R2=CH3, R4=H, R5=CH2CH3, R6=H, Compound 58: Q is selected from the structure represented by Q2, A3=O, R1=CH3, R2=CH3, R4=CH3, R5=CH3, R6=H, Compound 59: Q is selected from the structure represented by Q2, A3=O, R1=CH3, R2=CH3, R4=CH3, R5=CH2CH3, R6=H, Compound 60: Q is selected from the structure represented by Q2, A3=O, R1=CH3, R2=CH3, R4=CH2CH3, R5=CH3, R6=H, Compound 61: Q is selected from the structure represented by Q2, A3=O, R1=CH3, R2=CH3, R4=CH2CH3, R5=CH2CH3, R6=H, Compound 62: Q is selected from the structure represented by Q2, A3=O, R1=CH3, R2=CH3, R4=CH2CH2CH3, R5=CH3, R6=H, Compound 63: Q is selected from the structure represented by Q2, A3=O, R1=CH3, R2=CH3, R4=CH2CH2CH3, R5=CH2CH3, R6=H, Compound 64: Q is selected from the structure represented by Q2, A3=O, R1=CH3, R2=CH3, R4=CH(CH3)2, R5=CH3, R6=H, Compound 65: Q is selected from the structure represented by Q2, A3=O, R1=CH3, R2=CH3, R4=CH(CH3)2, R5=CH2CH3, R6=H, Compound 66: Q is selected from the structure represented by Q2, A3=O, R1=CH3, R2=CH3, R4=CF3, R5=CH3, R6=H, Compound 67: Q is selected from the structure represented by Q2, A3=O, R1=CH3, R2=CH3, R4=CF3, R5=CH2CH3, R6=H, Compound 68: Q is selected from the structure represented by Q2, A3=O, R1=CH3, R2=CH3, R4= TIFF2025539307000027.tif6170, R5=CH3, R6=H, Compound 69: Q is selected from the structure represented by Q2, A3=O, R1=CH3, R2=CH3, R4= TIFF2025539307000028.tif6170, R5=CH2CH3, R6=H, Compound 70: Q is selected from the structure represented by Q2, A3=O, R1=CH2CH3, R2=CH3, R4=H, R5=CH3, R6=H, Compound 71: Q is selected from the structure represented by Q2, A3=O, R1=CH2CH3, R2=CH3, R4=H, R5=CH2CH3, R6=H, Compound 72: Q is selected from the structure represented by Q2, A3=O, R1=CH2CH3, R2=CH3, R4=CH3, R5=CH3, R6=H, Compound 73: Q is selected from the structure represented by Q2, A3=O, R1=CH2CH3, R2=CH3, R4=CH3, R5=CH2CH3, R6=H, Compound 74: Q is selected from the structure represented by Q2, A3=O, R1=CH2CH3, R2=CH3, R4=CH2CH3, R5=CH3, R6=H, Compound 75: Q is selected from the structure represented by Q2, A3=O, R1=CH2CH3, R2=CH3, R4=CH2CH3, R5=CH2CH3, R6=H, Compound 76: Q is selected from the structure represented by Q2, A3=O, R1=CH2CH3, R2=CH3, R4=CH2CH2CH3, R5=CH3, R6=H, Compound 77: Q is selected from the structure represented by Q2, A3=O, R1=CH2CH3, R2=CH3, R4=CH2CH2CH3, R5=CH2CH3, R6=H, Compound 78: Q is selected from the structure represented by Q2, A3=O, R1=CH2CH3, R2=CH3, R4=CH(CH3)2, R5=CH3, R6=H, Compound 79: Q is selected from the structure represented by Q2, A3=O, R1=CH2CH3, R2=CH3, R4=CH(CH3)2, R5=CH2CH3, R6=H, Compound 80: Q is selected from the structure represented by Q2, A3=O, R1=CH2CH3, R2=CH3, R4=CF3, R5=CH3, R6=H, Compound 81: Q is selected from the structure represented by Q2, A3=O, R1=CH2CH3, R2=CH3, R4=CF3, R5=CH2CH3, R6=H, Compound 82: Q is selected from the structure represented by Q2, A3=O, R1=CH2CH3, R2=CH3, R4= TIFF2025539307000029.tif6170, R5=CH3, R6=H, Compound 83: Q is selected from the structure represented by Q2, A3=O, R1=CH2CH3, R2=CH3, R4= TIFF2025539307000030.tif6170, R5=CH2CH3, R6=H, Compound 84: Q is selected from the structure represented by Q2, A3=O, R1=CH2CH2CH3, R2=CH3, R4=H, R5=CH3, R6=H, Compound 85: Q is selected from the structure represented by Q2, A3=O, R1=CH2CH2CH3, R2=CH3, R4=H, R5=CH2CH3, R6=H, Compound 86: Q is selected from the structure represented by Q2, A3=O, R1=CH2CH2CH3, R2=CH3, R4=CH3, R5=CH3, R6=H, Compound 87: Q is selected from the structure represented by Q2, A3=O, R1=CH2CH2CH3, R2=CH3, R4=CH3, R5=CH2CH3, R6=H, Compound 88: Q is selected from the structure represented by Q2, A3=O, R1=CH2CH2CH3, R2=CH3, R4=CH2CH3, R5=CH3, R6=H, Compound 89: Q is selected from the structure represented by Q2, A3=O, R1=CH2CH2CH3, R2=CH3, R4=CH2CH3, R5=CH2CH3, R6=H, Compound 90: Q is selected from the structure represented by Q2, A3=O, R1=CH2CH2CH3, R2=CH3, R4=CH2CH2CH3, R5=CH3, R6=H, Compound 91: Q is selected from the structure represented by Q2, A3=O, R1=CH2CH2CH3, R2=CH3, R4=CH2CH2CH3, R5=CH2CH3, R6=H, Compound 92: Q is selected from the structure represented by Q2, A3=O, R1=CH2CH2CH3, R2=CH3, R4=CH(CH3)2, R5=CH3, R6=H, Compound 93: Q is selected from the structure represented by Q2, A3=O, R1=CH2CH2CH3, R2=CH3, R4=CH(CH3)2, R5=CH2CH3, R6=H, Compound 94: Q is selected from the structure represented by Q2, A3=O, R1=CH2CH2CH3, R2=CH3, R4=CF3, R5=CH3, R6=H, Compound 95: Q is selected from the structure represented by Q2, A3=O, R1=CH2CH2CH3, R2=CH3, R4=CF3, R5=CH2CH3, R6=H, Compound 96: Q is selected from the structure represented by Q2, A3=O, R1=CH2CH2CH3, R2=CH3, R4= TIFF2025539307000031.tif6170, R5=CH3, R6=H, Compound 97: Q is selected from the structure represented by Q2, A3=O, R1=CH2CH2CH3, R2=CH3, R4= TIFF2025539307000032.tif6170, R5=CH2CH3, R6=H, Compound 98: Q is selected from the structure represented by Q2, A3=O, R1=CH(CH3)2, R2=CH3, R4=H, R5=CH3, R6=H, Compound 99: Q is selected from the structure represented by Q2, A3=O, R1=CH(CH3)2, R2=CH3, R4=H, R5=CH2CH3, R6=H, Compound 100: Q is selected from the structure represented by Q2, A3=O, R1=CH(CH3)2, R2=CH3, R4=CH3, R5=CH3, R6=H, Compound 101: Q is selected from the structure represented by Q2, A3=O, R1=CH(CH3)2, R2=CH3, R4=CH3, R5=CH2CH3, R6=H, Compound 102: Q is selected from the structure represented by Q2, A3=O, R1=CH(CH3)2, R2=CH3, R4=CH2CH3, R5=CH3, R6=H, Compound 103: Q is selected from the structure represented by Q2, A3=O, R1=CH(CH3)2, R2=CH3, R4=CH2CH3, R5=CH2CH3, R6=H, Compound 104: Q is selected from the structure represented by Q2, A3=O, R1=CH(CH3)2, R2=CH3, R4=CH2CH2CH3, R5=CH3, R6=H, Compound 105: Q is selected from the structure represented by Q2, A3=O, R1=CH(CH3)2, R2=CH3, R4=CH2CH2CH3, R5=CH2CH3, R6=H, Compound 106: Q is selected from the structure represented by Q2, A3=O, R1=CH(CH3)2, R2=CH3, R4=CH(CH3)2, R5=CH3, R6=H, Compound 107: Q is selected from the structure represented by Q2, A3=O, R1=CH(CH3)2, R2=CH3, R4=CH(CH3)2, R5=CH2CH3, R6=H, Compound 108: Q is selected from the structure represented by Q2, A3=O, R1=CH(CH3)2, R2=CH3, R4=CF3, R5=CH3, R6=H, Compound 109: Q is selected from the structure represented by Q2, A3=O, R1=CH(CH3)2, R2=CH3, R4=CF3, R5=CH2CH3, R6=H, Compound 110: Q is selected from the structure represented by Q2, A3=O, R1=CH(CH3)2, R2=CH3, R4= TIFF2025539307000033.tif6170, R5=CH3, R6=H, Compound 111: Q is selected from the structure represented by Q2, A3=O, R1=CH(CH3)2, R2=CH3, R4= TIFF2025539307000034.tif6170, R5=CH2CH3, R6=H, Compound 112: Q is selected from the structure represented by Q2, A3=O, R1=CH2CH2CH2CH3, R2=CH3, R4=H, R5=CH3, R6=H, Compound 113: Q is selected from the structure represented by Q2, A3=O, R1=CH2CH2CH2CH3, R2=CH3, R4=H, R5=CH2CH3, R6=H, Compound 114: Q is selected from the structure represented by Q2, A3=O, R1=CH2CH2CH2CH3, R2=CH3, R4=CH3, R5=CH3, R6=H, Compound 115: Q is selected from the structure represented by Q2, A3=O, R1=CH2CH2CH2CH3, R2=CH3, R4=CH3, R5=CH2CH3, R6=H, Compound 116: Q is selected from the structure represented by Q2, A3=O, R1=CH2CH2CH2CH3, R2=CH3, R4=CH2CH3, R5=CH3, R6=H, Compound 117: Q is selected from the structure represented by Q2, A3=O, R1=CH2CH2CH2CH3, R2=CH3, R4=CH2CH3, R5=CH2CH3, R6=H, Compound 118: Q is selected from the structure represented by Q2, A3=O, R1=CH2CH2CH2CH3, R2=CH3, R4=CH2CH2CH3, R5=CH3, R6=H, Compound 119: Q is selected from the structure represented by Q2, A3=O, R1=CH2CH2CH2CH3, R2=CH3, R4=CH2CH2CH3, R5=CH2CH3, R6=H, Compound 120: Q is selected from the structure represented by Q2, A3=O, R1=CH2CH2CH2CH3, R2=CH3, R4=CH(CH3)2, R5=CH3, R6=H, Compound 121: Q is selected from the structure represented by Q2, A3=O, R1=CH2CH2CH2CH3, R2=CH3, R4=CH(CH3)2, R5=CH2CH3, R6=H, Compound 122: Q is selected from the structure represented by Q2, A3=O, R1=CH2CH2CH2CH3, R2=CH3, R4=CF3, R5=CH3, R6=H, Compound 123: Q is selected from the structure represented by Q2, A3=O, R1=CH2CH2CH2CH3, R2=CH3, R4=CF3, R5=CH2CH3, R6=H, Compound 124: Q is selected from the structure represented by Q2, A3=O, R1=CH2CH2CH2CH3, R2=CH3, R4= TIFF2025539307000035.tif6170, R5=CH3, R6=H, Compound 125: Q is selected from the structure represented by Q2, A3=O, R1=CH2CH2CH2CH3, R2=CH3, R4= TIFF2025539307000036.tif6170, R5=CH2CH3, R6=H, Compound 126: Q is selected from the structure represented by Q2, A3=O, R1=C(CH3)3, R2=CH3, R4=H, R5=CH3, R6=H, Compound 127: Q is selected from the structure represented by Q2, A3=O, R1=C(CH3)3, R2=CH3, R4=H, R5=CH2CH3, R6=H, Compound 128: Q is selected from the structure represented by Q2, A3=O, R1=C(CH3)3, R2=CH3, R4=CH3, R5=CH3, R6=H, Compound 129: Q is selected from the structure represented by Q2, A3=O, R1=C(CH3)3, R2=CH3, R4=CH3, R5=CH2CH3, R6=H, Compound 130: Q is selected from the structure represented by Q2, A3=O, R1=C(CH3)3, R2=CH3, R4=CH2CH3, R5=CH3, R6=H, Compound 131: Q is selected from the structure represented by Q2, A3=O, R1=C(CH3)3, R2=CH3, R4=CH2CH3, R5=CH2CH3, R6=H, Compound 132: Q is selected from the structure represented by Q2, A3=O, R1=C(CH3)3, R2=CH3, R4=CH2CH2CH3, R5=CH3, R6=H, Compound 133: Q is selected from the structure represented by Q2, A3=O, R1=C(CH3)3, R2=CH3, R4=CH2CH2CH3, R5=CH2CH3, R6=H, Compound 134: Q is selected from the structure represented by Q2, A3=O, R1=C(CH3)3, R2=CH3, R4=CH(CH3)2, R5=CH3, R6=H, Compound 135: Q is selected from the structure represented by Q2, A3=O, R1=C(CH3)3, R2=CH3, R4=CH(CH3)2, R5=CH2CH3, R6=H, Compound 136: Q is selected from the structure represented by Q2, A3=O, R1=C(CH3)3, R2=CH3, R4=CF3, R5=CH3, R6=H, Compound 137: Q is selected from the structure represented by Q2, A3=O, R1=C(CH3)3, R2=CH3, R4=CF3, R5=CH2CH3, R6=H, Compound 138: Q is selected from the structure represented by Q2, A3=O, R1=C(CH3)3, R2=CH3, R4= TIFF2025539307000037.tif6170, R5=CH3, R6=H, Compound 139: Q is selected from the structure represented by Q2, A3=O, R1=C(CH3)3, R2=CH3, R4= TIFF2025539307000038.tif6170, R5=CH2CH3, R6=H, Compound 140: Q is selected from the structure represented by Q2, A3=S, R1=CH3, R2=CH3, R4=CH3, R5=CH3, R6=(CH3CH2)2NCO, Compound 141: Q is selected from the structure represented by Q2, A3=O, R1=CH3, R2=CH3, R4=CH3, R5=CH3, R6=(CH3CH2CH2)2NCO, Compound 142: Q is selected from the structure represented by Q2, A3=O, R1=CH2CH3, R2=CH3, R4=CH3, R5=CH3, R6=(CH3CH2CH2)2NCO, Compound 143: Q is selected from the structure represented by Q2, A3=O, R1=CH(CH3)2, R2=CH3, R4=CH3, R5=CH3, R6=(CH3CH2CH2)2NCO, Compound 144: Q is selected from the structure represented by Q2, A3=O, R1=CH3, R2=CH3, R4= TIFF2025539307000039.tif6170, R5=CH3, R6=(CH3CH2CH2)2NCO, Compound 145: Q is selected from the structure represented by Q2, A3=S, R1=CH3, R2=CH3, R4=CH3, R5=CH3, R6=(CH3OCH2CH2)2NCO, Compound 146: Q is selected from the structure represented by Q2, A3=S, R1=CH3, R2=CH3, R4=CH3, R5=CH3, R6= TIFF2025539307000040.tif15170, Compound 147: Q is selected from the structure represented by Q2, A3=S, R1=CH3, R2=CH3, R4=CH3, R5=CH3, R6= TIFF2025539307000041.tif19170, Compound 148: Q is selected from the structure represented by Q2, A3=S, R1=CH3, R2=CH3, R4=CH3, R5=CH3, R6= TIFF2025539307000042.tif20170, Compound 149: Q is selected from the structure represented by Q2, A3=O, R1=CH3, R2=CH3, R4=CH3, R5=CH3, R6= TIFF2025539307000043.tif20170, Compound 150: Q is selected from the structure represented by Q2, A3=O, R1=CH2CH3, R2=CH3, R4=CH3, R5=CH3, R6= TIFF2025539307000044.tif20170, Compound 151: Q is selected from the structure represented by Q2, A3=O, R1=CH(CH3)2, R2=CH3, R4=CH3, R5=CH3, R6= TIFF2025539307000045.tif20170, Compound 152: Q is selected from the structure represented by Q2, A3=O, R1=CH3, R2=CH3, R4= TIFF2025539307000046.tif6170, R5=CH3, R6= TIFF2025539307000047.tif20170, Compound 153: Q is selected from the structure represented by Q2, A3=O, R1=CH2CH3, R2=CH3, R4= TIFF2025539307000048.tif6170, R5=CH3, R6= TIFF2025539307000049.tif20170, Compound 154: Q is selected from the structure represented by Q2, A3=O, R1=CH3, R2=CH3, R4=CH3, R5=CH3, R6= TIFF2025539307000050.tif20170, Compound 155: Q is selected from the structure represented by Q2, A3=O, R1=CH2CH3, R2=CH3, R4=CH3, R5=CH3, R6= TIFF2025539307000051.tif20170, Compound 156: Q is selected from the structure represented by Q2, A3=O, R1=CH2CH2CH3, R2=CH3, R4=CH3, R5=CH3, R6= TIFF2025539307000052.tif20170, Compound 157: Q is selected from the structure represented by Q2, A3=O, R1=CH(CH3)2, R2=CH3, R4=CH3, R5=CH3, R6= TIFF2025539307000053.tif20170, Compound 158: Q is selected from the structure represented by Q2, A3=O, R1=CH3, R2=CH3, R4=H, R5=CH3, R6= TIFF2025539307000054.tif20170, Compound 159: Q is selected from the structure represented by Q2, A3=O, R1=CH2CH3, R2=CH3, R4=H, R5=CH3, R6= TIFF2025539307000055.tif20170, Compound 160: Q is selected from the structure represented by Q2, A3=O, R1=CH2CH2CH3, R2=CH3, R4=H, R5=CH3, R6= TIFF2025539307000056.tif20170, Compound 161: Q is selected from the structure represented by Q2, A3=O, R1=CH(CH3)2, R2=CH3, R4=H, R5=CH3, R6= TIFF2025539307000057.tif20170, Compound 162: Q is selected from the structure represented by Q2, A3=O, R1=CH3, R2=CH3, R4= TIFF2025539307000058.tif6170, R5=CH3, R6= TIFF2025539307000059.tif20170, Compound 163: Q is selected from the structure represented by Q2, A3=O, R1=CH2CH3, R2=CH3, R4= TIFF2025539307000060.tif6170, R5=CH3, R6= TIFF2025539307000061.tif20170, Compound 164: Q is selected from the structure represented by Q2, A3=O, R1=CH2CH2CH3, R2=CH3, R4= TIFF2025539307000062.tif6170, R5=CH3, R6= TIFF2025539307000063.tif20170, Compound 165: Q is selected from the structure represented by Q2, A3=O, R1=CH(CH3)2, R2=CH3, R4= TIFF2025539307000064.tif6170, R5=CH3, R6= TIFF2025539307000065.tif20170, Compound 166: Q is selected from the structure represented by Q2, A3=O, R1=CH3, R2=CH3, R4=CH3, R5=CH3, R6= TIFF2025539307000066.tif25170, Compound 167: Q is selected from the structure represented by Q2, A3=O, R1=CH2CH3, R2=CH3, R4=CH3, R5=CH3, R6= TIFF2025539307000067.tif25170, Compound 168: Q is selected from the structure represented by Q2, A3=O, R1=CH2CH2CH3, R2=CH3, R4=CH3, R5=CH3, R6= TIFF2025539307000068.tif25170, Compound 169: Q is selected from the structure represented by Q2, A3=O, R1=CH(CH3)2, R2=CH3, R4=CH3, R5=CH3, R6= TIFF2025539307000069.tif25170, Compound 170: Q is selected from the structure represented by Q2, A3=O, R1=CH3, R2=CH3, R4=H, R5=CH3, R6= TIFF2025539307000070.tif25170, Compound 171: Q is selected from the structure represented by Q2, A3=O, R1=CH2CH3, R2=CH3, R4=H, R5=CH3, R6= TIFF2025539307000071.tif25170, Compound 172: Q is selected from the structure represented by Q2, A3=O, R1=CH2CH2CH3, R2=CH3, R4=H, R5=CH3, R6= TIFF2025539307000072.tif25170, Compound 173: Q is selected from the structure represented by Q2, A3=O, R1=CH(CH3)2, R2=CH3, R4=H, R5=CH3, R6= TIFF2025539307000073.tif25170, Compound 174: Q is selected from the structure represented by Q2, A3=O, R1=CH3, R2=CH3, R4= TIFF2025539307000074.tif6170, R5=CH3, R6= TIFF2025539307000075.tif25170, Compound 175: Q is selected from the structure represented by Q2, A3=O, R1=CH2CH3, R2=CH3, R4= TIFF2025539307000076.tif6170, R5=CH3, R6= TIFF2025539307000077.tif25170, Compound 176: Q is selected from the structure represented by Q2, A3=O, R1=CH2CH2CH3, R2=CH3, R4= TIFF2025539307000078.tif6170, R5=CH3, R6= TIFF2025539307000079.tif25170, Compound 177: Q is selected from the structure represented by Q2, A3=O, R1=CH(CH3)2, R2=CH3, R4= TIFF2025539307000080.tif6170, R5=CH3, R6= TIFF2025539307000081.tif25170, Compound 178: Q is selected from the structure represented by Q2, A3=O, R1=CH3, R2=CH3, R4=CH3, R5=CH3, R6= TIFF2025539307000082.tif19170, Compound 179: Q is selected from the structure represented by Q2, A3=O, R1=CH2CH2CH3, R2=CH3, R4=CH3, R5=CH3, R6= TIFF2025539307000083.tif19170, Compound 180: Q is selected from the structure represented by Q2, A3=O, R1=CH3, R2=CH3, R4=H, R5=CH3, R6= TIFF2025539307000084.tif19170, Compound 181: Q is selected from the structure represented by Q2, A3=O, R1=CH2CH2CH3, R2=CH3, R4=H, R5=CH3, R6= TIFF2025539307000085.tif19170, Compound 182: Q is selected from the structure represented by Q2, A3=O, R1=CH3, R2=CH3, R4= TIFF2025539307000086.tif6170, R5=CH3, R6= TIFF2025539307000087.tif19170, Compound 183: Q is selected from the structure represented by Q2, A3=O, R1=CH2CH2CH3, R2=CH3, R4= TIFF2025539307000088.tif6170, R5=CH3, R6= TIFF2025539307000089.tif19170, Compound 184: Q is selected from the structure represented by Q2, A3=O, R1=CH2CH3, R2=CH3, R4=CH3, R5=CH3, R6= TIFF2025539307000090.tif25170, Compound 185: Q is selected from the structure represented by Q2, A3=O, R1=CH(CH3)2, R2=CH3, R4=CH3, R5=CH3, R6= TIFF2025539307000091.tif25170, Compound 186: Q is selected from the structure represented by Q2, A3=O, R1=CH2CH3, R2=CH3, R4=H, R5=CH3, R6= TIFF2025539307000092.tif25170, Compound 187: Q is selected from the structure represented by Q2, A3=O, R1=CH(CH3)2, R2=CH3, R4=H, R5=CH3, R6= TIFF2025539307000093.tif25170, Compound 188: Q is selected from the structure represented by Q2, A3=O, R1=CH2CH3, R2=CH3, R4= TIFF2025539307000094.tif6170, R5=CH3, R6= TIFF2025539307000095.tif25170, Compound 189: Q is selected from the structure represented by Q2, A3=O, R1=CH(CH3)2, R2=CH3, R4= TIFF2025539307000096.tif6170, R5=CH3, R6= TIFF2025539307000097.tif25170, Compound 190: Q is selected from the structure represented by Q2, A3=O, R1=CH2CH3, R2=CH3, R4=CH3, R5=CH2CH3, R6= TIFF2025539307000098.tif24170, Compound 191: Q is selected from the structure represented by Q2, A3=O, R1=CH3, R2=CH3, R4=H, R5=CH2CH3, R6= TIFF2025539307000099.tif24170, Compound 192: Q is selected from the structure represented by Q2, A3=O, R1=CH2CH2CH3, R2=CH3, R4= TIFF2025539307000100.tif6170, R5=CH2CH3, R6= TIFF2025539307000101.tif23170, Compound 193: Q is selected from the structure represented by Q2, A3=O, R1=CH(CH3)2, R2=CH3, R4= TIFF2025539307000102.tif6170, R5=CH2CH3, R6= TIFF2025539307000103.tif23170, Compound 194: Q is selected from the structure represented by Q2, A3=O, R1=CH3, R2=CH3, R4=CH3, R5=CH3, R6= TIFF2025539307000104.tif20170, Compound 195: Q is selected from the structure represented by Q2, A3=O, R1=CH2CH3, R2=CH3, R4=CH3, R5=CH3, R6= TIFF2025539307000105.tif20170, Compound 196: Q is selected from the structure represented by Q2, A3=O, R1=CH2CH2CH3, R2=CH3, R4=CH3, R5=CH3, R6= TIFF2025539307000106.tif20170, Compound 197: Q is selected from the structure represented by Q2, A3=O, R1=CH(CH3)2, R2=CH3, R4=CH3, R5=CH3, R6= TIFF2025539307000107.tif20170, Compound 198: Q is selected from the structure represented by Q2, A3=O, R1=CH3, R2=CH3, R4=H, R5=CH3, R6= TIFF2025539307000108.tif20170, Compound 199: Q is selected from the structure represented by Q2, A3=O, R1=CH2CH3, R2=CH3, R4=H, R5=CH3, R6= TIFF2025539307000109.tif20170, Compound 200: Q is selected from the structure represented by Q2, A3=O, R1=CH(CH3)2, R2=CH3, R4=H, R5=CH3, R6= TIFF2025539307000110.tif20170, Compound 201: Q is selected from the structure represented by Q2, A3=O, R1=CH3, R2=CH3, R4= TIFF2025539307000111.tif6170, R5=CH3, R6= TIFF2025539307000112.tif20170, Compound 202: Q is selected from the structure represented by Q2, A3=O, R1=CH2CH3, R2=CH3, R4= TIFF2025539307000113.tif6170, R5=CH3, R6= TIFF2025539307000114.tif20170, Compound 203: Q is selected from the structure represented by Q2, A3=O, R1=CH(CH3)2, R2=CH3, R4= TIFF2025539307000115.tif6170, R5=CH3, R6= TIFF2025539307000116.tif20170, Compound 204: Q is selected from the structure represented by Q2, A3=O, R1=CH3, R2=CH3, R4=CH3, R5=CH3, R6= TIFF2025539307000117.tif25170, Compound 205: Q is selected from the structure represented by Q2, A3=O, R1=CH2CH3, R2=CH3, R4=CH3, R5=CH3, R6= TIFF2025539307000118.tif25170, Compound 206: Q is selected from the structure represented by Q2, A3=O, R1=CH(CH3)2, R2=CH3, R4=CH3, R5=CH3, R6= TIFF2025539307000119.tif25170, Compound 207: Q is selected from the structure represented by Q2, A3=O, R1=CH3, R2=CH3, R4=H, R5=CH3, R6= TIFF2025539307000120.tif25170, Compound 208: Q is selected from the structure represented by Q2, A3=O, R1=CH2CH3, R2=CH3, R4=H, R5=CH3, R6= TIFF2025539307000121.tif25170, Compound 209: Q is selected from the structure represented by Q2, A3=O, R1=CH2CH2CH3, R2=CH3, R4=H, R5=CH3, R6= TIFF2025539307000122.tif25170, Compound 210: Q is selected from the structure represented by Q2, A3=O, R1=CH(CH3)2, R2=CH3, R4=H, R5=CH3, R6= TIFF2025539307000123.tif25170, Compound 211: Q is selected from the structure represented by Q2, A3=O, R1=CH2CH3, R2=CH3, R4= TIFF2025539307000124.tif6170, R5=CH3, R6= TIFF2025539307000125.tif25170, Compound 212: Q is selected from the structure represented by Q2, A3=O, R1=CH(CH3)2, R2=CH3, R4= TIFF2025539307000126.tif6170, R5=CH3, R6= TIFF2025539307000127.tif25170, Compound 213: Q is selected from the structure represented by Q2, A3=O, R1=CH3, R2=CH3, R4=CH3, R5=CH3, R6= TIFF2025539307000128.tif20170, Compound 214: Q is selected from the structure represented by Q2, A3=O, R1=CH2CH3, R2=CH3, R4=CH3, R5=CH3, R6= TIFF2025539307000129.tif20170, Compound 215: Q is selected from the structure represented by Q2, A3=O, R1=CH(CH3)2, R2=CH3, R4=CH3, R5=CH3, R6= TIFF2025539307000130.tif20170, Compound 216: Q is selected from the structure represented by Q2, A3=O, R1=CH3, R2=CH3, R4= TIFF2025539307000131.tif6170, R5=CH3, R6= TIFF2025539307000132.tif20170, Compound 217: Q is selected from the structure represented by Q2, A3=O, R1=CH(CH3)2, R2=CH3, R4= TIFF2025539307000133.tif6170, R5=CH3, R6= TIFF2025539307000134.tif20170, Compound 218: Q is selected from the structure represented by Q2, A3=O, R1=CH3, R2=CH3, R4=CH3, R5=CH3, R6= TIFF2025539307000135.tif19170, Compound 219: Q is selected from the structure represented by Q2, A3=O, R1=CH2CH3, R2=CH3, R4=CH3, R5=CH3, R6= TIFF2025539307000136.tif19170, Compound 220: Q is selected from the structure represented by Q2, A3=O, R1=CH(CH3)2, R2=CH3, R4=CH3, R5=CH3, R6= TIFF2025539307000137.tif19170, Compound 221: Q is selected from the structure represented by Q2, A3=O, R1=CH3, R2=CH3, R4= TIFF2025539307000138.tif6170, R5=CH3, R6= TIFF2025539307000139.tif19170, Compound 222: Q is selected from the structure represented by Q2, A3=O, R1=CH(CH3)2, R2=CH3, R4= TIFF2025539307000140.tif6170, R5=CH3, R6= TIFF2025539307000141.tif19170, Compound 223: Q is selected from the structure represented by Q2, A3=O, R1=CH3, R2=CH3, R4=CH3, R5=CH3, R6= TIFF2025539307000142.tif18170, Compound 224: Q is selected from the structure represented by Q2, A3=O, R1=CH2CH3, R2=CH3, R4=CH3, R5=CH3, R6= TIFF2025539307000143.tif18170, Compound 225: Q is selected from the structure represented by Q2, A3=O, R1=CH(CH3)2, R2=CH3, R4=CH3, R5=CH3, R6= TIFF2025539307000144.tif18170, Compound 226: Q is selected from the structure represented by Q2, A3=O, R1=CH(CH3)2, R2=CH3, R4= TIFF2025539307000145.tif6170, R5=CH3, R6= TIFF2025539307000146.tif18170, Compound 227: Q is selected from the structure represented by Q2, A3=O, R1=CH3, R2=CH3, R4=CH3, R5=CH3, R6= TIFF2025539307000147.tif24170, Compound 228: Q is selected from the structure represented by Q2, A3=O, R1=CH2CH3, R2=CH3, R4=CH3, R5=CH3, R6= TIFF2025539307000148.tif24170, Compound 229: Q is selected from the structure represented by Q2, A3=O, R1=CH(CH3)2, R2=CH3, R4=CH3, R5=CH3, R6= TIFF2025539307000149.tif24170, Compound 230: Q is selected from the structure represented by Q2, A3=O, R1=CH(CH3)2, R2=CH3, R4= TIFF2025539307000150.tif6170, R5=CH3, R6= TIFF2025539307000151.tif24170, Compound 231: Q is selected from the structure represented by Q2, A3=O, R1=CH3, R2=CH3, R4=CH3, R5=CH3, R6= TIFF2025539307000152.tif16170, Compound 232: Q is selected from the structure represented by Q2, A3=S, R1=CH3, R2=CH3, R4=CH3, R5=CH3, R6= TIFF2025539307000153.tif16170, Compound 233: Q is selected from the structure represented by Q2, A3=O, R1=CH2CH3, R2=CH3, R4=CH3, R5=CH3, R6= TIFF2025539307000154.tif16170, Compound 234: Q is selected from the structure represented by Q2, A3=O, R1=CH(CH3)2, R2=CH3, R4=CH3, R5=CH3, R6= TIFF2025539307000155.tif16170, Compound 235: Q is selected from the structure represented by Q2, A3=O, R1=CH3, R2=CH3, R4= TIFF2025539307000156.tif6170, R5=CH3, R6= TIFF2025539307000157.tif16170, Compound 236: Q is selected from the structure represented by Q2, A3=O, R1=CH2CH3, R2=CH3, R4= TIFF2025539307000158.tif6170, R5=CH3, R6= TIFF2025539307000159.tif16170, Compound 237: Q is selected from the structure represented by Q2, A3=O, R1=CH(CH3)2, R2=CH3, R4= TIFF2025539307000160.tif6170, R5=CH3, R6= TIFF2025539307000161.tif16170, Compound 238: Q is selected from the structure represented by Q2, A3=O, R1=CH3, R2=CH3, R4=CH3, R5=CH3, R6= TIFF2025539307000162.tif16170, Compound 239: Q is selected from the structure represented by Q2, A3=O, R1=CH2CH3, R2=CH3, R4=CH3, R5=CH3, R6= TIFF2025539307000163.tif16170, Compound 240: Q is selected from the structure represented by Q2, A3=O, R1=CH(CH3)2, R2=CH3, R4=CH3, R5=CH3, R6= TIFF2025539307000164.tif16170, Compound 241: Q is selected from the structure represented by Q2, A3=O, R1=CH3, R2=CH3, R4= TIFF2025539307000165.tif6170, R5=CH3, R6= TIFF2025539307000166.tif16170, Compound 242: Q is selected from the structure represented by Q2, A3=O, R1=CH2CH3, R2=CH3, R4= TIFF2025539307000167.tif6170, R5=CH3, R6= TIFF2025539307000168.tif16170, Compound 243: Q is selected from the structure represented by Q2, A3=O, R1=CH(CH3)2, R2=CH3, R4= TIFF2025539307000169.tif6170, R5=CH3, R6= TIFF2025539307000170.tif16170, Compound 244: Q is selected from the structure represented by Q2, A3=O, R1=CH3, R2=CH3, R4=CH3, R5=CH3, R6= TIFF2025539307000171.tif14170, Compound 245: Q is selected from the structure represented by Q2, A3=S, R1=CH3, R2=CH3, R4=CH3, R5=CH3, R6= TIFF2025539307000172.tif14170, Compound 246: Q is selected from the structure represented by Q2, A3=O, R1=CH(CH3)2, R2=CH3, R4=CH3, R5=CH3, R6= TIFF2025539307000173.tif14170, Compound 247: Q is selected from the structure represented by Q2, A3=O, R1=CH3, R2=CH3, R4= TIFF2025539307000174.tif6170, R5=CH3, R6= TIFF2025539307000175.tif14170, Compound 248: Q is selected from the structure represented by Q2, A3=O, R1=CH2CH3, R2=CH3, R4= TIFF2025539307000176.tif6170, R5=CH3, R6= TIFF2025539307000177.tif14170, Compound 249: Q is selected from the structure represented by Q2, A3=O, R1=CH(CH3)2, R2=CH3, R4= TIFF2025539307000178.tif6170, R5=CH3, R6= TIFF2025539307000179.tif14170, Compound 250: Q is selected from the structure represented by Q2, A3=O, R1=CH3, R2=CH3, R4=CH3, R5=CH3, R6= TIFF2025539307000180.tif14170, Compound 251: Q is selected from the structure represented by Q2, A3=O, R1=CH(CH3)2, R2=CH3, R4=CH3, R5=CH3, R6= TIFF2025539307000181.tif14170, Compound 252: Q is selected from the structure represented by Q2, A3=O, R1=CH3, R2=CH3, R4= TIFF2025539307000182.tif6170, R5=CH3, R6= TIFF2025539307000183.tif14170, Compound 253: Q is selected from the structure represented by Q2, A3=O, R1=CH2CH3, R2=CH3, R4= TIFF2025539307000184.tif6170, R5=CH3, R6= TIFF2025539307000185.tif14170, Compound 254: Q is selected from the structure represented by Q2, A3=O, R1=CH(CH3)2, R2=CH3, R4= TIFF2025539307000186.tif6170, R5=CH3, R6= TIFF2025539307000187.tif14170, Compound 255: Q is selected from the structure represented by Q2, A3=O, R1=CH3, R2=CH3, R4=CH3, R5=CH3, R6= TIFF2025539307000188.tif18170, Compound 256: Q is selected from the structure represented by Q2, A3=S, R1=CH3, R2=CH3, R4=CH3, R5=CH3, R6= TIFF2025539307000189.tif18170, Compound 257: Q is selected from the structure represented by Q2, A3=O, R1=CH(CH3)2, R2=CH3, R4=CH3, R5=CH3, R6= TIFF2025539307000190.tif18170, Compound 258: Q is selected from the structure represented by Q2, A3=O, R1=CH3, R2=CH3, R4= TIFF2025539307000191.tif6170, R5=CH3, R6= TIFF2025539307000192.tif18170, Compound 259: Q is selected from the structure represented by Q2, A3=O, R1=CH2CH3, R2=CH3, R4= TIFF2025539307000193.tif6170, R5=CH3, R6= TIFF2025539307000194.tif18170, Compound 260: Q is selected from the structure represented by Q2, A3=O, R1=CH(CH3)2, R2=CH3, R4= TIFF2025539307000195.tif6170, R5=CH3, R6= The file is TIFF2025539307000196.tif18170.

[0026] The compounds of formula I of the present application or their tautomers have herbicidal activity and can be used in agriculture to control a wide variety of weeds.

[0027] The present application further provides the use of the oxadiazolone compounds or tautomers thereof described in the above technical solutions in controlling weeds.

[0028] In some specific implementations, the weeds are one or more selected from broadleaf weeds or grass weeds.

[0029] In some specific implementations, the weed is one or more selected from velvetleaf, Solanum nigrum (nightshade), crabgrass, and barnyard grass.

[0030] The present application further provides a herbicidal composition, comprising the oxadiazolone compound or its tautomer described in the above technical solution and an adjuvant. The present application does not particularly limit the selection of the adjuvant, and the appropriate adjuvant may be selected depending on the required formulation. The compound of general formula I or its tautomer is used as the active ingredient, and its content by weight percentage may be 0.1 to 99%, preferably 0.5 to 50%.

[0031] The herbicidal composition of the present application can be applied in various formulations. The compound of the present application is usually formulated by dissolving or dispersing it in a carrier so that it can be easily dispersed when used as a herbicide. For example, these chemical formulations can be formulated as wettable powders, emulsifiable concentrates, etc. Therefore, these compositions contain at least one liquid or solid carrier, and usually require the addition of an appropriate surfactant.

[0032] The present application further provides a method for controlling weeds, comprising applying to crops the herbicidal composition described in the above technical solution.

[0033] Specifically, the present application involves applying a herbicidally effective amount of the herbicidal composition of the present application to the weeds, the area where the weeds grow, or the surface of the growth medium. An effective amount is suitably 1 gram to 1,000 grams per hectare, and preferably 10 to 500 grams per hectare. For certain applications, the herbicidal composition of the present application may also contain one or more other herbicides, which can provide additional benefits and effects. [Effects of the Invention]

[0034] The present applicant has substituted the position between the sulfonyl group and Cl on the benzene ring of a benzoyl compound with an oxadiazolone group represented by formula (a), thereby obtaining an oxadiazolone compound, which not only has unexpectedly high herbicidal activity against a variety of weeds, but is also relatively safe for a variety of crops, such as corn and rice. Experimental results have shown that the compound provided herein has relatively good herbicidal activity and can effectively control weeds, such as barnyard grass, crabgrass, and velvetleaf, at low doses, achieving good herbicidal effect while at the same time being relatively safe for crops. [ka] DETAILED DESCRIPTION OF THE INVENTION

[0035] In order to clarify the objectives, technical solutions and advantages of the embodiments of the present application, the following clearly and completely describes the technical solutions in the embodiments of the present application, and it is obvious that the described embodiments are only some of the embodiments of the present application, not all of the embodiments, and all other embodiments obtained by those skilled in the art based on the embodiments of the present application without any creative work fall within the scope of protection of the present application.

[0036] In addition, in order to better explain the present application, many specific details are provided in the following specific embodiments. As will be understood by those skilled in the art, the present application can be similarly implemented without specific details. In some examples, materials, elements, methods, means, etc. that are well known to those skilled in the art are not described in detail, but are used to emphasize the gist of the present application.

[0037] In this application, the terms used are generally defined as follows: Halogen: refers to fluorine, chlorine, bromine or iodine. Alkyl group: a straight-chain or branched alkyl group, such as a methyl group, an ethyl group, a propyl group, an isopropyl group, an n-butyl group or a tert-butyl group. Cycloalkyl group: A substituted or unsubstituted cyclic alkyl group, such as a cyclopropyl group, a cyclopentyl group, or a cyclohexyl group, with a methyl group, halogen, or the like as a substituent. Halogenated alkyl group: A linear or branched alkyl group in which some or all of the hydrogen atoms on the alkyl group may be substituted with halogen atoms, such as a chloromethoxy group, a dichloromethoxy group, a trichloromethoxy group, a fluoromethoxy group, a difluoromethoxy group, or a trifluoromethyl group. Alkoxy group: A straight or branched alkyl group attached to the structure via an oxygen atom. Halogenated alkoxy group: A linear or branched alkoxy group in which some or all of the hydrogen atoms on the alkoxy group may be substituted with halogen atoms, such as a chloromethoxy group, a dichloromethoxy group, a trichloromethoxy group, a fluoromethoxy group, a difluoromethoxy group, or a trifluoromethoxy group. Alkylamino group: A straight or branched alkyl group is attached to the structure via a nitrogen atom. Halogenated alkylamino group: A linear or branched alkylamino group, in which some or all of the hydrogen atoms on the alkylamino group may be substituted with halogen atoms. Cycloalkylamino group: A substituted or unsubstituted cyclic alkylamino group that is attached to the structure via a nitrogen atom, such as a cyclopentylamino group or a cyclohexylamino group. Heterocycle: A cyclic hydrocarbon containing a heteroatom such as N, O, or S in the ring. Examples include furan, thiophene, morpholine, cyclohexaneimine, pyrazole, or piperidine. Heterocyclic amino group: A heterocyclic ring is attached to the structure via a nitrogen atom. Tautomers: structural isomers with different energies that can be interconverted via a low energy barrier. If tautomers are possible (e.g., in a solution), chemical equilibrium of tautomers can be achieved. For example, proton tautomers include interconversions via proton transfer, such as keto-enol isomerization and imine-enamine isomerization. In this application, keto-enol tautomerization occurs depending on external conditions (e.g., solvent, pH, etc.).

[0038] Some compounds of the present application can be explained using the specific compounds shown in Tables 1, 2 and 3, but the present application is not limited to these compounds.

[0039] [Table 1] Specific compounds 1 to 30 [ka] TIFF2025539307000199.tif160170

[0040] [Table 2] Specific compounds 31 to 55 [ka] TIFF2025539307000201.tif193170

[0041] [Table 3] Specific compounds 56-260 [ka] JPEG2025539307000203.jpg200170TIFF2025539307000204.tif192170TIFF2025539307000205.t if196170TIFF2025539307000206.tif186170TIFF2025539307000207.tif196170TIFF20255393070 00208.tif182170TIFF2025539307000209.tif182170TIFF2025539307000210.tif188170TIFF202 5539307000211.tif183170TIFF2025539307000212.tif194170TIFF2025539307000213.tif179170

[0042] The molecular formulas, mass spectra, nuclear magnetic hydrogen spectra and carbon spectrum data of some compounds are shown in Table 4. [Table 4] Molecular formulas, mass spectra, nuclear magnetic hydrogen spectra, and carbon spectrum data for some compounds TIFF2025539307000214.tif188170TIFF2025539307000215.tif194170TIFF2025539307000216.tif181170TIFF2025539307000217.tif194170TIFF2025539307000218.tif207170TIFF2025539307000219.tif182170TIFF2025539307000220.tif174170TIFF2025539307000221.tif186170TIFF2025539307000222.tif202170TIFF2025539307000223.tif182170TIFF2025539307000224.tif191170TIFF2025539307000225.tif212170TIFF2025539307000226.tif180170TIFF2025539307000227.tif191170TIFF2025539307000228.tif211170TIFF2025539307000229.tif206170TIFF2025539307000230.tif202170TIFF2025539307000231.tif202170TIFF2025539307000232.tif211170TIFF2025539307000233.tif202170TIFF2025539307000234.tif197170TIFF2025539307000235.tif211170TIFF2025539307000236.tif210170TIFF2025539307000237.tif211170TIFF2025539307000238.tif210170TIFF2025539307000239.tif173170TIFF2025539307000240.tif184170TIFF2025539307000241.tif197170TIFF2025539307000242.tif202170TIFF2025539307000243.tif187170TIFF2025539307000244.tif202170TIFF2025539307000245.tif181170TIFF2025539307000246.tif181170TIFF2025539307000247.tif196170TIFF2025539307000248.tif206170TIFF2025539307000249.tif206170TIFF2025539307000250.tif21 1170TIFF2025539307000251.tif176170TIFF2025539307000252.tif211170TIFF2025539307000253.tif184170TIFF2025539307000254.tif210170.

[0043] The compound of the present invention represented by the general formula (I-3) can be prepared by the following method. [ka] In the above formula, the compound of general formula II and R 10 A5H is reacted with a base and a suitable solvent at a temperature between -10°C and the boiling point for 0.5 to 24 hours to obtain a compound of general formula I-3. The suitable solvent is selected from acetonitrile, DMF, HMPA, dimethyl sulfoxide, tetrahydrofuran, etc. The suitable base is selected from sodium hydrogen carbonate, sodium carbonate, potassium carbonate, triethylamine, etc.

[0044] The method for preparing the compound of general formula II is as follows. [ka] In the above formula, the compound of general formula III is reacted with a suitable chlorinating reagent at a temperature between 0°C and the boiling point for 0.5 to 4 hours to obtain the compound of general formula II, where the suitable chlorinating reagent is selected from thionyl chloride, oxalyl chloride, phosphorus trichloride, etc.

[0045] The method for preparing the compound of general formula III is as follows. [ka] In the above scheme, the compound of general formula IV is reacted with a base and a catalyst in a suitable solvent at a temperature between -10°C and the boiling point for 0.5 to 24 hours to obtain the compound of general formula III. Suitable solvents include dichloromethane, 1,2-dichloroethane, chloroform, carbon tetrachloride, benzene, toluene, ethyl acetate, acetonitrile, tetrahydrofuran, dioxane, N,N-dimethylformamide, and dimethyl sulfoxide. Suitable bases include sodium carbonate, potassium carbonate, and triethylamine. Suitable catalysts include sodium carbonate, potassium carbonate, and acetone cyanohydrin.

[0046] The method for preparing the compound of general formula IV is as follows. [ka] In the formula, the compound of formula V is first reacted with an acid halide reagent in a suitable solvent at a temperature between -10°C and the boiling point of the solvent for 0.5 to 24 hours to obtain the corresponding acid chloride. The acid halide reagent is selected from oxalyl chloride, thionyl chloride, phosphorus oxychloride, phosphorus trichloride, or solid phosgene, and the suitable solvent is selected from dichloromethane, 1,2-dichloroethane, chloroform, carbon tetrachloride, benzene, toluene, acetonitrile, tetrahydrofuran, or dioxane. The corresponding acid chloride thus prepared is reacted in the presence of a suitable base in the same or a different solvent, 1,3-cyclohexanedione, at a temperature between -10°C and the boiling point of the corresponding solvent for 0.5 to 24 hours to obtain the compound of formula IV. The suitable base is selected from triethylamine, pyridine, sodium carbonate, potassium carbonate, sodium methoxide, or potassium tert-butoxide.

[0047] The method for preparing the compound of formula V is as follows. [ka] Compounds of general formula VI (see "Nohyaku" (Pesticides), 2017, 56(5):326-327, 379: Synthesis of cyclic sulfoketones for cornfield herbicides) and compounds of general formula VII (commercially available products) were reacted in the presence of a suitable solvent and base at a temperature ranging from 0°C to the boiling point of the solvent for 0.5 to 24 hours to obtain compounds of general formula V. Suitable solvents include acetonitrile, N,N-dimethylformamide, dimethyl sulfoxide, methanol, ethanol, isopropyl alcohol, and the like. Suitable bases include sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium methoxide, potassium tert-butoxide, and the like.

[0048] The compound of formula I-2 can be prepared as follows. [ka] In the above formula, the compound of formula VIII and the compound of formula R6Cl are reacted in a suitable solvent under the action of a base for 0.5-24 hours to obtain the compound of formula I-2. Suitable solvents include dichloromethane, 1,2-dichloroethane, chloroform, carbon tetrachloride, benzene, toluene, acetonitrile, tetrahydrofuran, and dioxane. Suitable bases include sodium carbonate, potassium carbonate, and triethylamine.

[0049] Taking A3 as an example, the preparation method of the compound of general formula VIII is as follows: [ka] The reaction conditions for preparing the compound of formula VIII from the compound of formula V and the compound of formula IX refer to the reaction conditions for preparing the compound of formula III from the compound of formula IV, and the details are omitted here.

[0050] The compounds of formula I-1 and formula III are tautomers depending on environmental conditions, for example, keto-enol tautomers occur depending on the solvent, pH, etc.

[0051] The herbicidal compositions, oxadiazolone compounds and uses thereof provided in the present application will be further described below with reference to examples.

[0052] Example 1 Synthesis of Compound 1 (1) Synthesis of 2-chloro-3-[(5-methyl-2-oxo-1,3,4-oxadiazol-3(2H)yl)methyl)]-4-methanesulfonylbenzoic acid [ka] A reaction flask was charged with 3-bromomethyl-2-chloro-4-methanesulfonylbenzoic acid (6.5 g, 20 mmol), 5-methyl-1,3,4-oxadiazol-2(3H)-one (2 g, 20 mmol), potassium carbonate (4.1 g, 30 mmol), and acetonitrile (60 mL). The mixture was heated and refluxed for 3 hours. The solvent was removed by distillation under reduced pressure, and water (30 mL) was added. While stirring, the pH was adjusted to 2-3 with 10% diluted hydrochloric acid. White crystals were gradually precipitated, which were suction filtered and dried to obtain 4.8 g of a white solid, with a yield of 70%. (2) 2-chloro-3-[(5-methyl-2-oxo-1,3,4-oxadiazol-3(2H)yl)methyl)]-4-methanesulfonylbenzoic acid (3-oxocyclohex-1-ene) ester [ka] A reaction flask was charged with 2-chloro-3-[(5-methyl-2-oxo-1,3,4-oxadiazol-3(2H)yl)methyl]-4-methanesulfonylbenzoic acid (6.9 g, 20 mmol) and toluene (50 mL). Thionyl chloride (14.3 g, 120 mmol) was slowly added, and the mixture was heated to reflux for 4 hours. The solvent and excess thionyl chloride were removed under reduced pressure. Dichloromethane (60 mL), 1,3-cyclohexanedione (2.3 g, 20.5 mmol), and triethylamine (3.2 g, 32 mmol) were added dropwise. The mixture was stirred at room temperature for 1 hour. Water (50 mL) was added, and the aqueous phase was extracted twice with dichloromethane (30 mL). The oil phases were combined, and the solvent was removed by distillation to yield 8.3 g of a pale yellow solid, which was used directly in the next step. (3) Synthesis of Compound 1 (2-{2-chloro-3-[(5-methyl-2-oxo-1,3,4-oxadiazol-3(2H)yl)methyl]-4-methanesulfonylbenzoyl}-1,3-cyclohexanedione) [ka] Add dichloromethane (60 mL), triethylamine (2.4 g, 24 mmol), and 2 drops of acetone cyanohydrin to a reaction flask. Add 8.3 g of the solid obtained in the previous step and stir at room temperature overnight. Add water (60 mL) and stir for 0.5 hours. Adjust the pH to 7-8 with 10% dilute hydrochloric acid. Extract the aqueous phase twice with ethyl acetate (60 mL). Combine the organic phases, wash with saturated brine (60 mL), dry over anhydrous magnesium sulfate, and remove the solvent under reduced pressure to obtain 8.1 g of a pale yellow solid with a purity of 97%.

[0053] Example 2 Synthesis of Compound 53 (1) 3-{2-chloro-3-[(2-chloro-6-oxocyclohexane-1-alkenyl)carbonyl]-6-(methanesulfonyl)benzyl}-5-methyl-1,3,4-oxadiazole-2(3H)-alkane [ka] Into a reaction flask were added 2-{2-chloro-3-[(5-methyl-2-oxo-1,3,4-oxadiazol-3(2H)yl)methyl]-4-methanesulfonylbenzoyl}-1,3-cyclohexanedione (8.8 g, 20 mmol) and dichloromethane (50 mL), and thionyl chloride (4.7 g, 40 mmol) was slowly added. The mixture was stirred at room temperature for 4 hours, and the solvent and excess thionyl chloride were removed under reduced pressure to obtain 8.2 g of a yellow solid with a purity of 96%. (2) Synthesis of Compound 53 (3-{2-chloro-3-[(2-benzylthio-6-oxocyclohexane-1-alkenyl)carbonyl]-6-(methanesulfonyl)benzyl}-5-methyl-1,3,4-oxadiazole-2(3H)-alkane) [ka] Into a 100ml four-neck flask, 3-{2-chloro-3-[(2-chloro-6-oxocyclohexane-1-alkenyl)carbonyl]-6-(methanesulfonyl)benzyl}-5-methyl-1,3,4-oxadiazole-2(3H)-alkane (6 grams, 13 mmol), 30 grams of HMPA, 1.6 grams of benzyl mercaptan were added, and the mixture was stirred uniformly. The temperature was lowered to 0°C, and 0.38 grams of sodium hydrogen was gradually added in batches to the four-neck flask. The raw material reaction was measured until the sample was complete, and the pH was adjusted to 3 with acidic water. The mixture was extracted with ethyl acetate, and the ethyl acetate phase was collected and rotary evaporated under negative pressure to obtain the crude product. The mixture was stirred overnight in dichloromethane-sodium bicarbonate aqueous solution, and the dichloromethane phase was collected and rotary evaporated to obtain 5.6 grams of a yellow solid, with a purity of 90%.

[0054] Example 3 Synthesis of Compound 100 (1) Synthesis of 2-chloro-3-[(5-methyl-2-oxo-1,3,4-oxadiazol-3(2H)yl)methyl)]-4-isopropylsulfonylbenzoic acid [ka] A reaction flask was charged with 3-bromomethyl-2-chloro-4-isopropylsulfonylbenzoic acid (14.2 g, 40 mmol), 5-methyl-1,3,4-oxadiazol-2(3H)-one (4 g, 40 mmol), 30% sodium hydroxide solution (8 g, 60 mmol), and ethanol (100 mL). The mixture was heated and refluxed for 3 hours, the solvent was removed by distillation under reduced pressure, water (50 mL) was added, and the pH was adjusted to 2-3 with 10% diluted hydrochloric acid while stirring. White crystals were gradually precipitated, which were suction filtered and dried to obtain 12 g of a white solid, with a yield of 80%. (2) Synthesis of 2-chloro-3-[(5-methyl-2-oxo-1,3,4-oxadiazol-3(2H)yl)methyl]-4-isopropylsulfonylbenzoic acid (1,3-dimethylpyrazol-5-yl) ester [ka] A reaction flask was charged with 2-chloro-3-[(5-methyl-2-oxo-1,3,4-oxadiazol-3(2H)yl)methyl]-4-isopropylsulfonylbenzoic acid (7.5 g, 20 mmol) and dichloroethane (50 mL). Oxalyl chloride (7.6 g, 60 mmol) was slowly added, and the mixture was heated to reflux for 4 hours. The solvent and excess oxalyl chloride were removed under reduced pressure. Dichloroethane (60 mL) and 1,3-dimethyl-5-hydroxypyrazole (2.3 g, 20.5 mmol) were added, and triethylamine (3.2 g, 32 mmol) was added dropwise. The mixture was stirred at room temperature for 1 hour. Water (50 mL) was added, and the aqueous phase was extracted twice with dichloroethane (30 mL). The oil phases were combined, the solvent was removed, and the residue was purified by column chromatography to obtain 6.1 g of a pale yellow solid in 65% yield. (3) Synthesis of Compound 100 (1,3-dimethyl-4-{2-chloro-3-[(5-methyl-2-oxo-1,3,4-oxadiazol-3(2H)yl)methyl]-4-isopropylsulfonylbenzoyl}-5-hydroxypyrazole) [ka] 2-Chloro-3-[(5-methyl-2-oxo-1,3,4-oxadiazol-3(2H)yl)methyl]-4-isopropylsulfonylbenzoic acid (1,3-dimethylpyrazol-5-yl) ester (6.1 g, 13 mmol), dichloromethane (100 mL), triethylamine (1.9 g, 19 mmol), and acetone cyanohydrin (2 mL) were added to a reaction flask and reacted at room temperature for 12 hours. The reaction mixture was extracted with water (60 mL), stirred for 0.5 hours, and the pH was adjusted to 2-3 with 10% dilute hydrochloric acid. The aqueous phase was extracted twice with ethyl acetate (100 mL * 2). The organic phases were combined, washed with saturated brine (60 mL), dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure to obtain 5.8 g of a pale yellow solid. The yield was 96%.

[0055] Example 4 Synthesis of Compound 171 [ka] A reaction flask was charged with 1-methyl-3-trifluoromethyl-4-pyrazolecarboxylic acid (4.5 g, 23 mmol) and dichloroethane (80 mL). Thionyl chloride (7.1 g, 60 mmol) was slowly added, and the mixture was heated under reflux for 4 hours. The solvent and excess thionyl chloride were distilled off under reduced pressure. Dichloroethane (80 mL), 3-{2-chloro-3-[(1-methyl-5-hydroxy-1H-pyrazol-4-yl)carbonyl]-6-ethanesulfonylbenzyl}-5-methyl-1,3,4-oxadiazol-2(3H)-one (7.2 g, 15.8 mmol) were added, and triethylamine (3 g, 30 mmol) was added dropwise. The mixture was stirred at room temperature for 1 hour, and water (50 mL) was added. The aqueous phase was extracted twice with dichloroethane (30 mL * 2). The oil phases were combined, washed with saturated brine (60 ml), dried over anhydrous magnesium sulfate, the solvent was removed under reduced pressure, and the residue was separated by column chromatography to obtain 10.1 g of a solid, with a yield of 70%.

[0056] Example 5 Measurement of herbicidal activity Seeds of broadleaf weeds (velvetleaf and nightshade) or grass weeds (crabgrass and barnyard grass) were sown in plastic cups containing nutrient soil. After sowing, the seeds were covered with soil, tamped down, watered, and then cultivated in a greenhouse according to conventional methods. The weeds were treated by spraying the foliage after they reached the 2- to 3-leaf stage. Each test compound of the present invention was dissolved in acetone, followed by the addition of polysorbate 80. The solution was diluted with a certain amount of water to a certain solubility and sprayed on the plants using a spray tower. The test was repeated three times. After air-drying in the shade, the weeds were placed in a greenhouse and maintained according to conventional methods. The growth and development of the weeds were observed, and the control effect of the test compound on the weeds was visually observed periodically. The results were expressed as 0 to 100%, with "0" indicating no control effect and "100%" indicating complete destruction or significant control.

[0057] Test results show that the compounds of general formula I generally have high control effects against broadleaf weeds and grass weeds. Among some of the tested compounds, for example, compounds 1, 5, 6, 11, 16, 32, 45, 46, 47, 49, 51, 53, 58, 154, 166, 194, 215, 223, 224, 227, 228, 231, 233, 238, 244, 246, and 250, showed relatively good control effects against crabgrass when applied at a rate of 300 g ai / ha, with the control effects all being greater than 80%. For example, compounds 1, 5, 32, 56, 58, 59, 68, 72, 82, 96, 100, 149, 150, 152, 153, 154, 166, 194, 201, 215, 223, 224, 227, 228, 233, and 238 showed relatively good control effects against crabgrass when applied at a rate of 300 g ai / ha. ai / ha, the control effect was relatively good against barnyardgrass, and all of the control effects were greater than 80%. For example, compounds 1, 5, 48, 53, 58, 68, 72, 96, 100, 150, 152, 154, 166, 171, 178, 180, 182, 185, 187, 190, 201, 215, 223, 224, 225, 226, 227, 228, 230, 231, 233, 235, 236, 238, 240, 241, 242, 243, 244, 245, 246, 248, 249, 250, 251, 252, 253 and 254 were applied at a dose of 300g. At ai / ha, it has relatively good control effects against velvetleaf and nightshade, and the control effects are both greater than 90%.

[0058] Based on the above test method, compounds 1, 32, 49, 166, 194, 201, 204, 218, 224, and 228 were selected and tested for herbicidal activity simultaneously with control compounds A, B, and C. The activity data against velvetleaf, nightshade, crabgrass, and barnyard grass are shown in Table 5, which also shows the test results for the compounds provided in the examples of this application against seedling weeds (weeds after emergence).

[0059] Table 5: Seedling weed test results for compounds provided in the examples of this application TIFF2025539307000271.tif255170TIFF2025539307000272.tif27170

[0060] Here, the control compound A is as follows: [ka] Control Compound B is as follows: [ka] Control Compound C is as follows: [ka]

[0061] As can be seen from Table 5, compared with the control compounds A, B and C, compounds 1, 32, 49, 166, 194, 201, 204, 218, 224 and compound 228 provided herein all have good herbicidal activity against velvetleaf, nightshade, crabgrass, barnyard grass and the like at different doses.

[0062] Example 6: Measurement of the safety of corn and rice Corn and rice seeds were sown in plastic cups containing nutrient soil. After sowing, the seeds were covered with soil, pressed down, and watered. They were then cultivated in a greenhouse according to standard methods. The plants were sprayed on the stems and leaves at the 2-3 leaf stage. Each test compound was dissolved in acetone, followed by the addition of polysorbate 80. The solution was diluted with a certain amount of water to a certain solubility, and sprayed on the plants using a spray tower. The test was repeated three times. After air-drying in the shade, the corn and rice plants were placed in a greenhouse and maintained according to standard methods. The growth and development of the corn and rice plants were observed, and the safety of the test compounds on the corn and rice plants was periodically visually inspected. The safety ranking scale was expressed as 0-100%, with "0" indicating no damage to the plants and "100%" indicating complete or significant damage to the plants. Some test results are shown in Table 6, which shows the safety test results for the compounds provided in the examples of this application on corn and rice.

[0063] [Table 6] Safety test results for compounds provided in the examples of this application on corn and rice TIFF2025539307000276.tif206170

[0064] Control Compound A is as follows: [ka] Control Compound B is as follows: [ka] Control Compound C is as follows: [ka]

[0065] As can be seen from Table 6, compared with the control compounds A, B and C, compounds 6, 58, 100, 201, 224, 228 and compound 233 provided herein do not have significant inhibitory effects on corn and rice at different doses.

[0066] Finally, it should be noted that the above embodiments are only for illustrating the technical solutions of the present application, and are not limiting thereof, and although the present application has been described in detail with reference to the above embodiments, those skilled in the art will understand that the technical solutions described in the above embodiments can still be modified or some technical features thereof can be equivalently substituted, and these modifications or substitutions will not cause the essence of the corresponding technical solutions to deviate from the spirit and scope of the technical solutions of the present application. [Industrial Applicability]

[0067] The present applicant has substituted the position between the sulfonyl group and Cl on the benzene ring of a benzoyl compound with an oxadiazolone group represented by formula (a), thereby obtaining an oxadiazolone compound, which not only has unexpectedly high herbicidal activity against a variety of weeds, but is also relatively safe for a variety of crops, such as corn and rice. Experimental results have shown that the compound provided herein has relatively good herbicidal activity and can effectively control weeds, such as barnyard grass, crabgrass, and velvetleaf, at low doses, achieving good herbicidal effect while at the same time being relatively safe for crops.

Claims

1. An oxadiazolone compound represented by formula (I) or a tautomer thereof. 【Chemistry 1】 (In formula (I), R １ and R ２ are independently unsubstituted or halogen, nitro group, C １ ~C ６ Alkyl groups, halogenated C １ ~C ６ alkyl group of C １ ~C ６ Alkoxy group or halogenated C １ ~C ６ C substituted with 1 to 3 groups independently selected from alkoxy groups １ ~C ６ or an alkyl group of C ３ ~C ６ and selected from the cycloalkyl groups Q is selected from the structures represented by Q1, Q2, or Q3; 【change】 Here, A １ , A ２ , A ３ , A ４ and A ５ are independently selected from O or S; R ３ and R １０ are independently hydrogen, unsubstituted or halogen, a nitro group, C １ ~C ６ Alkyl groups, halogenated C １ ~C ６ alkyl group of C １ ~C ６ Alkoxy groups, halogenated C １ ~C ６ C substituted with 1 to 3 groups independently selected from alkoxy groups, phenyl groups, and halogenated phenyl groups １ ~C ６ alkyl group of C ３ ~C ６ a cycloalkyl group of C １ ~C ６ an alkoxy group, a phenyl group, or a benzyl group; n is an integer from 1 to 6, R ４ is hydrogen, halogen, unsubstituted or halogen, nitro group, C １ ~C ６ Alkyl groups, halogenated C １ ~C ６ alkyl group of C １ ~C ６ Alkoxy group or halogenated C １ ~C ６ C substituted with 1 to 3 groups independently selected from alkoxy groups １ ~C ６ alkyl group of C ３ ~C ６ or a cycloalkyl group of C １ ~C ６ and selected from the alkoxy groups R ５ is hydrogen, unsubstituted or halogen, a nitro group, C １ ~C ６ Alkyl groups, halogenated C １ ~C ６ alkyl group of C １ ~C ６ Alkoxy group or halogenated C １ ~C ６ C substituted with 1 to 3 groups independently selected from alkoxy groups １ ~C ６ or an alkyl group of C ３ ~C ６ and selected from the cycloalkyl groups R ６ is hydrogen, a structure represented by formula (1), unsubstituted or halogen, a nitro group, C １ ~C ６ Alkyl groups, halogenated C １ ~C ６ alkyl group of C １ ~C ６ Alkoxy group or halogenated C １ ~C ６ C substituted with 1 to 3 groups independently selected from alkoxy groups １ ~C ６ alkyl group of C ３ ~C ６ and a C3 to C8 heterocyclic alkyl group; 【Chemistry 2】 In formula (1), A ６ is N or CR ９ Selected from R ９ is hydrogen, unsubstituted or halogen, a nitro group, C １ ~C ６ Alkyl groups, halogenated C １ ~C ６ alkyl group of C １ ~C ６ Alkoxy group or halogenated C １ ~C ６ C substituted with 1 to 3 groups independently selected from alkoxy groups １ ~C ６ alkyl group of C ３ ~C ６ or a cycloalkyl group of C １ ~C ６ and selected from the alkoxy groups R ７ and R ８ are independently hydrogen, unsubstituted or halogen, a nitro group, C １ ~C ６ Alkyl groups, halogenated C １ ~C ６ alkyl group of C １ ~C ６ Alkoxy group or halogenated C １ ~C ６ C substituted with 1 to 3 groups independently selected from alkoxy groups １ ~C ６ alkyl group of C ３ ~C ６ or a cycloalkyl group of C １ ~C ６ and R ７ and R ８ are not simultaneously H, Or, R ７ , R ８ is the A where it is located ６ and unsubstituted or halogen, nitro group, C １ ~C ６ alkyl group of C ３ ~C ６ Cycloalkyl groups of halogenated C １ ~C ６ alkyl group of C １ ~C ６ Alkoxy group or halogenated C １ ~C ６ C containing 0 to 3 heteroatoms, substituted with 1 to 3 groups independently selected from alkoxy groups ３ ~C ８ wherein the heteroatom is selected from oxygen, sulfur, or nitrogen.

2. Q is selected from the structures represented by Q1-1; R ３ is H, C １ ~C ４ or an alkyl group of C １ ~C ４ and wherein the halogenated alkyl group is selected from the group consisting of R １ and R ２ is independently C １ ~C ４ alkyl group of C ３ ~C ６ or a cycloalkyl group of C １ ~C ４ and wherein the halogenated alkyl group is selected from the group consisting of Or, Q is selected from the structures represented by Q3-1; R １０ is H, C １ ~C ４ alkyl group of C １ ~C ４ halogenated alkyl groups, phenyl groups, halogenated phenyl groups, phenyl-substituted C １ ~C ４ C alkyl group or halogenated phenyl group substituted １ ~C ４ and selected from the alkyl groups R １ and R ２ is independently C １ ~C ４ alkyl group of C ３ ~C ６ or a cycloalkyl group of C １ ~C ４ and wherein the halogenated alkyl group is selected from the group consisting of Or, Q is selected from the structures represented by Q2-1; X １ is selected from C or N, and X ２ is selected from C, N, O or S, and X １ and X ２ are not simultaneously C, R １１ is H, halogen, C １ ~C ４ alkyl group of C ３ ~C ６ or a cycloalkyl group of C １ ~C ４ and wherein the halogenated alkyl group is selected from the group consisting of m is an integer from 1 to 3, R ４ is hydrogen, halogen, C １ ~C ４ Alkyl groups, halogenated C １ ~C ４ alkyl group of C ３ ~C ６ Cycloalkyl groups of halogenated C ３ ~C ６ a cycloalkyl group of C １ ~C ４ Alkoxy groups, halogenated C １ ~C ４ and selected from the alkoxy groups R ５ is hydrogen, C １ ~C ４ Alkyl group or halogenated C １ ~C ４ and selected from the alkyl groups R １ and R ２ is independently C １ ~C ４ alkyl group of C ３ ~C ６ or a cycloalkyl group of C １ ~C ４ 2. The oxadiazolone compound or a tautomer thereof according to claim 1, wherein the halogenated alkyl group is selected from the group consisting of:

3. R １ and R ２ are independently —CH ３ , -CH ２ CH ３ , -CH ２ CH ２ CH ３ , -CH(CH ３ ) ２ , -C(CH ３ ) ３ , -CH ２ CH ２ CH ２ CH ３ , -CF ３ , -CH ２ CF ３ , -CH ２ CH ２ CF ３ , -CH(CF ３ ) ２ , -C(CF ３ ) ３ , -CHCH ３ CF ３ , -C(CH ３ ) ２ CF ３ or CCH ２ (CF ３ ) ２ 3. The oxadiazolone compound or a tautomer thereof according to claim 2, wherein the compound is selected from the group consisting of:

4. R １０ is H, -CH ３ , -CH ２ CH ３ , -CH ２ CH ２ CH ３ , -CH(CH ３ ) ２ , -C(CH ３ ) ３ , -CH ２ CH ２ CH ２ CH ３ , phenyl group, chlorophenyl group, dichlorophenyl group, C ６ H ５ CH ２ -, C ６ H ４ ClCH ２ - or C ６ H ３ Cl ２ CH ２ Selected from - R １１ is H, CH ３ , C.F. ３ , -CH ２ CH ３、 4. The oxadiazolone compound or a tautomer thereof according to claim 3, wherein the oxadiazolone group is selected from a cyclopropyl group and Cl.

5. R ６ is selected from hydrogen or a structure represented by formula (1), 【Transformation 3】 In formula (1), A ６ is selected from N, and R ７ and R ８ are independently hydrogen, C １ -C4 alkyl groups, halogenated C １ ~C ４ alkyl group of C ３ ~C ６ a cycloalkyl group of C １ ~C ４ Alkoxy group or halogenated C １ ~C ４ and R ７ and R ８ are not simultaneously H, Or, A ６ is selected from N or C, R ７ , R ８ is the A where it is located ６ and unsubstituted or halogen, nitro group, C １ ~C ４ Alkyl groups, halogenated C １ ~C ４ alkyl group of C １ ~C ４ Alkoxy group or halogenated C １ ~C ４ C containing 1 to 3 heteroatoms, substituted with 1 to 3 groups independently selected from alkoxy groups ３ ~C ８ 2. The oxadiazolone compound or a tautomer thereof according to claim 1, wherein the heteroatom is selected from oxygen, sulfur, and nitrogen.

6. R ６ is selected from the following structures: Here, R １ , R ３ , R ４ , R ６ are independently selected from hydrogen, halogen, a C1-C4 alkyl group, a halogenated C1-C4 alkyl group, or a C3-C6 cycloalkyl group; R ２ , R ５ , R ７ are independently selected from hydrogen, a C1-C4 alkyl group, a halogenated C1-C4 alkyl group, or a C3-C6 cycloalkyl group.

7. selected from the following compounds: Compound 1: Q is selected from the structures represented by Q1-1, and R １ =CH ３ , R ２ =CH ３ , R ３ = H, Compound 2: Q is selected from the structures represented by Q1-1, and R １ =CH ３ , R ２ =CH ２ CH ３ , R ３ = H, Compound 3: Q is selected from the structures represented by Q1-1, and R １ =CH ３ , R ２ =CH ２ CH ２ CH ３ , R ３ = H, Compound 4: Q is selected from the structures represented by Q1-1, and R １ =CH ３ , R ２ =C(CH ３ ) ３ , R ３ = H, Compound 5: Q is selected from the structures represented by Q1-1, and R １ =CH ３ , R ２ =CF ３ , R ３ = H, Compound 6: Q is selected from the structures represented by Q1-1, and R １ =CH ２ CH ３ , R ２ =CH ３ , R ３ = H, Compound 7: Q is selected from the structures represented by Q1-1, and R １ =CH ２ CH ３ , R ２ =CH ２ CH ３ , R ３ = H, Compound 8: Q is selected from the structures represented by Q1-1, and R １ =CH ２ CH ３ , R ２ =CH ２ CH ２ CH ３ , R ３ = H, Compound 9: Q is selected from the structures represented by Q1-1, and R １ =CH ２ CH ３ , R ２ =C(CH ３ ) ３ , R ３ = H, Compound 10: Q is selected from the structures represented by Q1-1, and R １ =CH ２ CH ３ , R ２ =CF ３ , R ３ = H, Compound 11: Q is selected from the structures represented by Q1-1, and R １ =CH ２ CH ２ CH ３ , R ２ =CH ３ , R ３ = H, Compound 12: Q is selected from the structures represented by Q1-1, and R １ =CH ２ CH ２ CH ３ , R ２ =CH ２ CH ３ , R ３ = H, Compound 13: Q is selected from the structures represented by Q1-1, and R １ =CH ２ CH ２ CH ３ , R ２ =CH ２ CH ２ CH ３ , R ３ = H, Compound 14: Q is selected from the structures represented by Q1-1, and R １ =CH ２ CH ２ CH ３ , R ２ =C(CH ３ ) ３ , R ３ = H, Compound 15: Q is selected from the structures represented by Q1-1, and R １ =CH ２ CH ２ CH ３ , R ２ =CF ３ , R ３ = H, Compound 16: Q is selected from the structures represented by Q1-1, and R １ =CH(CH ３ ) ２ , R ２ =CH ３ , R ３ = H, Compound 17: Q is selected from the structures represented by Q1-1, and R １ =CH(CH ３ ) ２ , R ２ =CH ２ CH ３ , R ３ = H, Compound 18: Q is selected from the structures represented by Q1-1, and R １ =CH(CH ３ ) ２ , R ２ =CH ２ CH ２ CH ３ , R ３ = H, Compound 19: Q is selected from the structures represented by Q1-1, and R １ =CH(CH ３ ) ２ , R ２ =C(CH ３ ) ３ , R ３ = H, Compound 20: Q is selected from the structures represented by Q1-1, and R １ =CH(CH ３ ) ２ , R ２ =CF ３ , R ３ = H, Compound 21: Q is selected from the structures represented by Q1-1, and R １ =CH ２ CH ２ CH ２ CH ３ , R ２ =CH ３ , R ３ = H, Compound 22: Q is selected from the structures represented by Q1-1, and R １ =CH ２ CH ２ CH ２ CH ３ , R ２ =CH ２ CH ３ , R ３ = H, Compound 23: Q is selected from the structures represented by Q1-1, and R １ =CH ２ CH ２ CH ２ CH ３ , R ２ =CH ２ CH ２ CH ３ , R ３ = H, Compound 24: Q is selected from the structures represented by Q1-1, and R １ =CH ２ CH ２ CH ２ CH ３ , R ２ =C(CH ３ ) ３ , R ３ = H, Compound 25: Q is selected from the structures represented by Q1-1, and R １ =CH ２ CH ２ CH ２ CH ３ , R ２ =CF ３ , R ３ = H, Compound 26: Q is selected from the structures represented by Q1-1, and R １ =C(CH ３ ) ３ , R ２ =CH ３ , R ３ = H, Compound 27: Q is selected from the structures represented by Q1-1, and R １ =C(CH ３ ) ３ , R ２ =CH ２ CH ３ , R ３ = H, Compound 28: Q is selected from the structures represented by Q1-1, and R １ =C(CH ３ ) ３ , R ２ =CH ２ CH ２ CH ３ , R ３ = H, Compound 29: Q is selected from the structures represented by Q1-1, and R １ =C(CH ３ ) ３ , R ２ =C(CH ３ ) ３ , R ３ = H, Compound 30: Q is selected from the structures represented by Q1-1, and R １ =C(CH ３ ) ３ , R ２ =CF ３ , R ３ = H, Compound 31: Q is selected from the structures represented by Q3, and R １ =CH ３ , R ２ =CH ３ , A ４ = O, A ５ = O, R １０ =CH ３ , Compound 32: Q is selected from the structures represented by Q3, and R １ =CH ３ , R ２ =CH ３ , A ４ = O, A ５ = O, R １０ =CH ２ CH ３ , Compound 33: Q is selected from the structures represented by Q3, and R １ =CH ３ , R ２ =CH ３ , A ４ = O, A ５ = O, R １０ =CH ２ CH ２ CH ３ , Compound 34: Q is selected from the structures represented by Q3, and R １ =CH ３ , R ２ =CH ３ , A ４ = O, A ５ = O, R １０ =CH(CH ３ ) ２ , Compound 35: Q is selected from the structures represented by Q3, and R １ =CH ３ , R ２ =CH ３ , A ４ = O, A ５ = O, R １０ =CH ２ CH ２ CH ２ CH ３ , Compound 36: Q is selected from the structures represented by Q3, and R １ =CH ３ , R ２ =CH ３ , A ４ = O, A ５ = O, R １０ =C(CH ３ ) ３ , Compound 37: Q is selected from the structures represented by Q3, and R １ =CH ３ , R ２ =CH ３ , A ４ = O, A ５ = O, R １０ = 、 Compound 38: Q is selected from the structures represented by Q3, and R １ =CH ３ , R ２ =CH ３ , A ４ = O, A ５ = O, R １０ = 、 Compound 39: Q is selected from the structures represented by Q3, and R １ =CH ３ , R ２ =CH ３ , A ４ = O, A ５ = O, R １０ = 、 Compound 40: Q is selected from the structures represented by Q3, and R １ =CH ３ , R ２ =CH ３ , A ４ = O, A ５ = O, R １０ = 、 Compound 41: Q is selected from the structures represented by Q3, and R １ =CH ３ , R ２ =CH ３ , A ４ = O, A ５ = O, R １０ = 、 Compound 42: Q is selected from the structures represented by Q3, and R １ =CH ３ , R ２ =CH ３ , A ４ = O, A ５ = O, R １０ = 、 Compound 43: Q is selected from the structures represented by Q3, and R １ =CH ３ , R ２ =CH ３ , A ４ = O, A ５ = O, R １０ = 、 Compound 44: Q is selected from the structures represented by Q3, and R １ =CH ３ , R ２ =CH ３ , A ４ = O, A ５ = S, R １０ =CH ３ , Compound 45: Q is selected from the structures represented by Q3, and R １ =CH ３ , R ２ =CH ３ , A ４ = O, A ５ = S, R １０ =CH ２ CH ３ , Compound 46: Q is selected from the structures represented by Q3, and R １ =CH ３ , R ２ =CH ３ , A ４ = O, A ５ = S, R １０ =CH ２ CH ２ CH ３ , Compound 47: Q is selected from the structures represented by Q3, and R １ =CH ３ , R ２ =CH ３ , A ４ = O, A ５ = S, R １０ =CH(CH ３ ) ２ , Compound 48: Q is selected from the structures represented by Q3, and R １ =CH ３ , R ２ =CH ３ , A ４ = O, A ５ = S, R １０ =CH ２ CH ２ CH ２ CH ３ , Compound 49: Q is selected from the structures represented by Q3, and R １ =CH ３ , R ２ =CH ３ , A ４ = O, A ５ = S, R １０ =C(CH ３ ) ３ , Compound 50: Q is selected from the structures represented by Q3, and R １ =CH ３ , R ２ =CH ３ , A ４ = O, A ５ = S, R １０ = 、 Compound 51: Q is selected from the structures represented by Q3, and R １ =CH ３ , R ２ =CH ３ , A ４ = O, A ５ = S, R １０ = 、 Compound 52: Q is selected from the structures represented by Q3, and R １ =CH ３ , R ２ =CH ３ , A ４ = O, A ５ = S, R １０ = 、 Compound 53: Q is selected from the structures represented by Q3, and R １ =CH ３ , R ２ =CH ３ , A ４ = O, A ５ = S, R １０ = 、 Compound 54: Q is selected from the structures represented by Q3, and R １ =CH ３ , R ２ =CH ３ , A ４ = O, A ５ = S, R １０ = 、 Compound 55: Q is selected from the structures represented by Q3, and R １ =CH ３ , R ２ =CH ３ , A ４ = O, A ５ = S, R １０ = 、 Compound 56: Q is selected from the structures represented by Q2, and A ３ = O, R １ =CH ３ , R ２ =CH ３ , R ４ = H, R ５ =CH ３ , R ６ = H, Compound 57: Q is selected from the structures represented by Q2, and A ３ = O, R １ =CH ３ , R ２ =CH ３ , R ４ = H, R ５ =CH ２ CH ３ , R ６ = H, Compound 58: Q is selected from the structures represented by Q2, and A ３ = O, R １ =CH ３ , R ２ =CH ３ , R ４ =CH ３ , R ５ =CH ３ , R ６ = H, Compound 59: Q is selected from the structures represented by Q2, and A ３ = O, R １ =CH ３ , R ２ =CH ３ , R ４ =CH ３ , R ５ =CH ２ CH ３ , R ６ = H, Compound 60: Q is selected from the structures represented by Q2, and A ３ = O, R １ =CH ３ , R ２ =CH ３ , R ４ =CH ２ CH ３ , R ５ =CH ３ , R ６ = H, Compound 61: Q is selected from the structures represented by Q2, and A ３ = O, R １ =CH ３ , R ２ =CH ３ , R ４ =CH ２ CH ３ , R ５ =CH ２ CH ３ , R ６ = H, Compound 62: Q is selected from the structures represented by Q2, and A ３ = O, R １ =CH ３ , R ２ =CH ３ , R ４ =CH ２ CH ２ CH ３ , R ５ =CH ３ , R ６ = H, Compound 63: Q is selected from the structures represented by Q2, and A ３ = O, R １ =CH ３ , R ２ =CH ３ , R ４ =CH ２ CH ２ CH ３ , R ５ =CH ２ CH ３ , R ６ = H, Compound 64: Q is selected from the structures represented by Q2, and A ３ = O, R １ =CH ３ , R ２ =CH ３ , R ４ =CH(CH ３ ) ２ , R ５ =CH ３ , R ６ = H, Compound 65: Q is selected from the structures represented by Q2, and A ３ = O, R １ =CH ３ , R ２ =CH ３ , R ４ =CH(CH ３ ) ２ , R ５ =CH ２ CH ３ , R ６ = H, Compound 66: Q is selected from the structures represented by Q2, and A ３ = O, R １ =CH ３ , R ２ =CH ３ , R ４ =CF ３ , R ５ =CH ３ , R ６ = H, Compound 67: Q is selected from the structures represented by Q2, and A ３ = O, R １ =CH ３ , R ２ =CH ３ , R ４ =CF ３ , R ５ =CH ２ CH ３ , R ６ = H, Compound 68: Q is selected from the structures represented by Q2, and A ３ = O, R １ =CH ３ , R ２ =CH ３ , R ４ = 、R ５ =CH ３ 、R ６ =H、 Compound 69: Q is selected from the structures represented by Q2, and A ３ = O, R １ =CH ３ , R ２ =CH ３ , R ４ = 、R ５ =CH ２ CH ３ 、R ６ =H、 Compound 70: Q is selected from the structures represented by Q2, and A ３ = O, R １ =CH ２ CH ３ , R ２ =CH ３ , R ４ = H, R ５ =CH ３ , R ６ = H, Compound 71: Q is selected from the structures represented by Q2, and A ３ = O, R １ =CH ２ CH ３ , R ２ =CH ３ , R ４ = H, R ５ =CH ２ CH ３ , R ６ = H, Compound 72: Q is selected from the structures represented by Q2, and A ３ = O, R １ =CH ２ CH ３ , R ２ =CH ３ , R ４ =CH ３ , R ５ =CH ３ , R ６ = H, Compound 73: Q is selected from the structures represented by Q2, and A ３ = O, R １ =CH ２ CH ３ , R ２ =CH ３ , R ４ =CH ３ , R ５ =CH ２ CH ３ , R ６ = H, Compound 74: Q is selected from the structures represented by Q2, and A ３ = O, R １ =CH ２ CH ３ , R ２ =CH ３ , R ４ =CH ２ CH ３ , R ５ =CH ３ , R ６ = H, Compound 75: Q is selected from the structures represented by Q2, and A ３ = O, R １ =CH ２ CH ３ , R ２ =CH ３ , R ４ =CH ２ CH ３ , R ５ =CH ２ CH ３ , R ６ = H, Compound 76: Q is selected from the structures represented by Q2, and A ３ = O, R １ =CH ２ CH ３ , R ２ =CH ３ , R ４ =CH ２ CH ２ CH ３ , R ５ =CH ３ , R ６ = H, Compound 77: Q is selected from the structures represented by Q2, and A ３ = O, R １ =CH ２ CH ３ , R ２ =CH ３ , R ４ =CH ２ CH ２ CH ３ , R ５ =CH ２ CH ３ , R ６ = H, Compound 78: Q is selected from the structures represented by Q2, and A ３ = O, R １ =CH ２ CH ３ , R ２ =CH ３ , R ４ =CH(CH ３ ) ２ , R ５ =CH ３ , R ６ = H, Compound 79: Q is selected from the structures represented by Q2, and A ３ = O, R １ =CH ２ CH ３ , R ２ =CH ３ , R ４ =CH(CH ３ ) ２ , R ５ =CH ２ CH ３ , R ６ = H, Compound 80: Q is selected from the structures represented by Q2, and A ３ = O, R １ =CH ２ CH ３ , R ２ =CH ３ , R ４ =CF ３ , R ５ =CH ３ , R ６ = H, Compound 81: Q is selected from the structures represented by Q2, and A ３ = O, R １ =CH ２ CH ３ , R ２ =CH ３ , R ４ =CF ３ , R ５ =CH ２ CH ３ , R ６ = H, Compound 82: Q is selected from the structures represented by Q2, and A ３ = O, R １ =CH ２ CH ３ , R ２ =CH ３ , R ４ = 、R ５ =CH ３ 、R ６ =H、 Compound 83: Q is selected from the structures represented by Q2, and A ３ = O, R １ =CH ２ CH ３ , R ２ =CH ３ , R ４ = 、R ５ =CH ２ CH ３ 、R ６ =H、 Compound 84: Q is selected from the structures represented by Q2, and A ３ = O, R １ =CH ２ CH ２ CH ３ , R ２ =CH ３ , R ４ = H, R ５ =CH ３ , R ６ = H, Compound 85: Q is selected from the structures represented by Q2, and A ３ = O, R １ =CH ２ CH ２ CH ３ , R ２ =CH ３ , R ４ = H, R ５ =CH ２ CH ３ , R ６ = H, Compound 86: Q is selected from the structures represented by Q2, and A ３ = O, R １ =CH ２ CH ２ CH ３ , R ２ =CH ３ , R ４ =CH ３ , R ５ =CH ３ , R ６ = H, Compound 87: Q is selected from the structures represented by Q2, and A ３ = O, R １ =CH ２ CH ２ CH ３ , R ２ =CH ３ , R ４ =CH ３ , R ５ =CH ２ CH ３ , R ６ = H, Compound 88: Q is selected from the structures represented by Q2, and A ３ = O, R １ =CH ２ CH ２ CH ３ , R ２ =CH ３ , R ４ =CH ２ CH ３ , R ５ =CH ３ , R ６ = H, Compound 89: Q is selected from the structures represented by Q2, and A ３ = O, R １ =CH ２ CH ２ CH ３ , R ２ =CH ３ , R ４ =CH ２ CH ３ , R ５ =CH ２ CH ３ , R ６ = H, Compound 90: Q is selected from the structures represented by Q2, and A ３ = O, R １ =CH ２ CH ２ CH ３ , R ２ =CH ３ , R ４ =CH ２ CH ２ CH ３ , R ５ =CH ３ , R ６ = H, Compound 91: Q is selected from the structures represented by Q2, and A ３ = O, R １ =CH ２ CH ２ CH ３ , R ２ =CH ３ , R ４ =CH ２ CH ２ CH ３ , R ５ =CH ２ CH ３ , R ６ = H, Compound 92: Q is selected from the structures represented by Q2, and A ３ = O, R １ =CH ２ CH ２ CH ３ , R ２ =CH ３ , R ４ =CH(CH ３ ) ２ , R ５ =CH ３ , R ６ = H, Compound 93: Q is selected from the structures represented by Q2, and A ３ = O, R １ =CH ２ CH ２ CH ３ , R ２ =CH ３ , R ４ =CH(CH ３ ) ２ , R ５ =CH ２ CH ３ , R ６ = H, Compound 94: Q is selected from the structures represented by Q2, and A ３ = O, R １ =CH ２ CH ２ CH ３ , R ２ =CH ３ , R ４ =CF ３ , R ５ =CH ３ , R ６ = H, Compound 95: Q is selected from the structures represented by Q2, and A ３ = O, R １ =CH ２ CH ２ CH ３ , R ２ =CH ３ , R ４ =CF ３ , R ５ =CH ２ CH ３ , R ６ = H, Compound 96: Q is selected from the structures represented by Q2, and A ３ = O, R １ =CH ２ CH ２ CH ３ , R ２ =CH ３ , R ４ = 、R ５ =CH ３ 、R ６ =H、 Compound 97: Q is selected from the structures represented by Q2, and A ３ = O, R １ =CH ２ CH ２ CH ３ , R ２ =CH ３ , R ４ = 、R ５ =CH ２ CH ３ 、R ６ =H、 Compound 98: Q is selected from the structures represented by Q2, and A ３ = O, R １ =CH(CH ３ ) ２ , R ２ =CH ３ , R ４ = H, R ５ =CH ３ , R ６ = H, Compound 99: Q is selected from the structures represented by Q2, and A ３ = O, R １ =CH(CH ３ ) ２ , R ２ =CH ３ , R ４ = H, R ５ =CH ２ CH ３ , R ６ = H, Compound 100: Q is selected from the structures represented by Q2, and A ３ = O, R １ =CH(CH ３ ) ２ , R ２ =CH ３ , R ４ =CH ３ , R ５ =CH ３ , R ６ = H, Compound 101: Q is selected from the structures represented by Q2, and A ３ = O, R １ =CH(CH ３ ) ２ , R ２ =CH ３ , R ４ =CH ３ , R ５ =CH ２ CH ３ , R ６ = H, Compound 102: Q is selected from the structures represented by Q2, and A ３ = O, R １ =CH(CH ３ ) ２ , R ２ =CH ３ , R ４ =CH ２ CH ３ , R ５ =CH ３ , R ６ = H, Compound 103: Q is selected from the structures represented by Q2, and A ３ = O, R １ =CH(CH ３ ) ２ , R ２ =CH ３ , R ４ =CH ２ CH ３ , R ５ =CH ２ CH ３ , R ６ = H, Compound 104: Q is selected from the structures represented by Q2, and A ３ = O, R １ =CH(CH ３ ) ２ , R ２ =CH ３ , R ４ =CH ２ CH ２ CH ３ , R ５ =CH ３ , R ６ = H, Compound 105: Q is selected from the structures represented by Q2, and A ３ = O, R １ =CH(CH ３ ) ２ , R ２ =CH ３ , R ４ =CH ２ CH ２ CH ３ , R ５ =CH ２ CH ３ , R ６ = H, Compound 106: Q is selected from the structures represented by Q2, and A ３ = O, R １ =CH(CH ３ ) ２ , R ２ =CH ３ , R ４ =CH(CH ３ ) ２ , R ５ =CH ３ , R ６ = H, Compound 107: Q is selected from the structures represented by Q2, and A ３ = O, R １ =CH(CH ３ ) ２ , R ２ =CH ３ , R ４ =CH(CH ３ ) ２ , R ５ =CH ２ CH ３ , R ６ = H, Compound 108: Q is selected from the structures represented by Q2, and A ３ = O, R １ =CH(CH ３ ) ２ , R ２ =CH ３ , R ４ =CF ３ , R ５ =CH ３ , R ６ = H, Compound 109: Q is selected from the structures represented by Q2, and A ３ = O, R １ =CH(CH ３ ) ２ , R ２ =CH ３ , R ４ =CF ３ , R ５ =CH ２ CH ３ , R ６ = H, Compound 110: Q is selected from the structures represented by Q2, and A ３ = O, R １ =CH(CH ３ ) ２ , R ２ =CH ３ , R ４ = 、R ５ =CH ３ 、R ６ =H、 Compound 111: Q is selected from the structures represented by Q2, and A ３ = O, R １ =CH(CH ３ ) ２ , R ２ =CH ３ , R ４ = 、R ５ =CH ２ CH ３ 、R ６ =H、 Compound 112: Q is selected from the structures represented by Q2, and A ３ = O, R １ =CH ２ CH ２ CH ２ CH ３ , R ２ =CH ３ , R ４ = H, R ５ =CH ３ , R ６ = H, Compound 113: Q is selected from the structures represented by Q2, and A ３ = O, R １ =CH ２ CH ２ CH ２ CH ３ , R ２ =CH ３ , R ４ = H, R ５ =CH ２ CH ３ , R ６ = H, Compound 114: Q is selected from the structures represented by Q2, and A ３ = O, R １ =CH ２ CH ２ CH ２ CH ３ , R ２ =CH ３ , R ４ =CH ３ , R ５ =CH ３ , R ６ = H, Compound 115: Q is selected from the structures represented by Q2, and A ３ = O, R １ =CH ２ CH ２ CH ２ CH ３ , R ２ =CH ３ , R ４ =CH ３ , R ５ =CH ２ CH ３ , R ６ = H, Compound 116: Q is selected from the structures represented by Q2, and A ３ = O, R １ =CH ２ CH ２ CH ２ CH ３ , R ２ =CH ３ , R ４ =CH ２ CH ３ , R ５ =CH ３ , R ６ = H, Compound 117: Q is selected from the structures represented by Q2, and A ３ = O, R １ =CH ２ CH ２ CH ２ CH ３ , R ２ =CH ３ , R ４ =CH ２ CH ３ , R ５ =CH ２ CH ３ , R ６ = H, Compound 118: Q is selected from the structures represented by Q2, and A ３ = O, R １ =CH ２ CH ２ CH ２ CH ３ , R ２ =CH ３ , R ４ =CH ２ CH ２ CH ３ , R ５ =CH ３ , R ６ = H, Compound 119: Q is selected from the structures represented by Q2, and A ３ = O, R １ =CH ２ CH ２ CH ２ CH ３ , R ２ =CH ３ , R ４ =CH ２ CH ２ CH ３ , R ５ =CH ２ CH ３ , R ６ = H, Compound 120: Q is selected from the structures represented by Q2, and A ３ = O, R １ =CH ２ CH ２ CH ２ CH ３ , R ２ =CH ３ , R ４ =CH(CH ３ ) ２ , R ５ =CH ３ , R ６ = H, Compound 121: Q is selected from the structures represented by Q2, and A ３ = O, R １ =CH ２ CH ２ CH ２ CH ３ , R ２ =CH ３ , R ４ =CH(CH ３ ) ２ , R ５ =CH ２ CH ３ , R ６ = H, Compound 122: Q is selected from the structures represented by Q2, and A ３ = O, R １ =CH ２ CH ２ CH ２ CH ３ , R ２ =CH ３ , R ４ =CF ３ , R ５ =CH ３ , R ６ = H, Compound 123: Q is selected from the structures represented by Q2, and A ３ = O, R １ =CH ２ CH ２ CH ２ CH ３ , R ２ =CH ３ , R ４ =CF ３ , R ５ =CH ２ CH ３ , R ６ = H, Compound 124: Q is selected from the structures represented by Q2, and A ３ = O, R １ =CH ２ CH ２ CH ２ CH ３ , R ２ =CH ３ , R ４ = 、R ５ =CH ３ 、R ６ =H、 Compound 125: Q is selected from the structures represented by Q2, and A ３ = O, R １ =CH ２ CH ２ CH ２ CH ３ , R ２ =CH ３ , R ４ = 、R ５ =CH ２ CH ３ 、R ６ =H、 Compound 126: Q is selected from the structures represented by Q2, and A ３ = O, R １ =C(CH ３ ) ３ , R ２ =CH ３ , R ４ = H, R ５ =CH ３ , R ６ = H, Compound 127: Q is selected from the structures represented by Q2, and A ３ = O, R １ =C(CH ３ ) ３ , R ２ =CH ３ , R ４ = H, R ５ =CH ２ CH ３ , R ６ = H, Compound 128: Q is selected from the structures represented by Q2, and A ３ = O, R １ =C(CH ３ ) ３ , R ２ =CH ３ , R ４ =CH ３ , R ５ =CH ３ , R ６ = H, Compound 129: Q is selected from the structures represented by Q2, and A ３ = O, R １ =C(CH ３ ) ３ , R ２ =CH ３ , R ４ =CH ３ , R ５ =CH ２ CH ３ , R ６ = H, Compound 130: Q is selected from the structures represented by Q2, and A ３ = O, R １ =C(CH ３ ) ３ , R ２ =CH ３ , R ４ =CH ２ CH ３ , R ５ =CH ３ , R ６ = H, Compound 131: Q is selected from the structures represented by Q2, and A ３ = O, R １ =C(CH ３ ) ３ , R ２ =CH ３ , R ４ =CH ２ CH ３ , R ５ =CH ２ CH ３ , R ６ = H, Compound 132: Q is selected from the structures represented by Q2, and A ３ = O, R １ =C(CH ３ ) ３ , R ２ =CH ３ , R ４ =CH ２ CH ２ CH ３ , R ５ =CH ３ , R ６ = H, Compound 133: Q is selected from the structures represented by Q2, and A ３ = O, R １ =C(CH ３ ) ３ , R ２ =CH ３ , R ４ =CH ２ CH ２ CH ３ , R ５ =CH ２ CH ３ , R ６ = H, Compound 134: Q is selected from the structures represented by Q2, and A ３ = O, R １ =C(CH ３ ) ３ , R ２ =CH ３ , R ４ =CH(CH ３ ) ２ , R ５ =CH ３ , R ６ = H, Compound 135: Q is selected from the structures represented by Q2, and A ３ = O, R １ =C(CH ３ ) ３ , R ２ =CH ３ , R ４ =CH(CH ３ ) ２ , R ５ =CH ２ CH ３ , R ６ = H, Compound 136: Q is selected from the structures represented by Q2, and A ３ = O, R １ =C(CH ３ ) ３ , R ２ =CH ３ , R ４ =CF ３ , R ５ =CH ３ , R ６ = H, Compound 137: Q is selected from the structures represented by Q2, and A ３ = O, R １ =C(CH ３ ) ３ , R ２ =CH ３ , R ４ =CF ３ , R ５ =CH ２ CH ３ , R ６ = H, Compound 138: Q is selected from the structures represented by Q2, and A ３ = O, R １ =C(CH ３ ) ３ , R ２ =CH ３ , R ４ = 、R ５ =CH ３ 、R ６ =H、 Compound 139: Q is selected from the structures represented by Q2, and A ３ = O, R １ =C(CH ３ ) ３ , R ２ =CH ３ , R ４ = 、R ５ =CH ２ CH ３ 、R ６ =H、 Compound 140: Q is selected from the structures represented by Q2, and A ３ = S, R １ =CH ３ , R ２ =CH ３ , R ４ =CH ３ , R ５ =CH ３ , R ６ = (CH ３ CH ２ ) ２ NCO, Compound 141: Q is selected from the structures represented by Q2, and A ３ = O, R １ =CH ３ , R ２ =CH ３ , R ４ =CH ３ , R ５ =CH ３ , R ６ = (CH ３ CH ２ CH ２ ) ２ NCO, Compound 142: Q is selected from the structures represented by Q2, and A ３ = O, R １ =CH ２ CH ３ , R ２ =CH ３ , R ４ =CH ３ , R ５ =CH ３ , R ６ = (CH ３ CH ２ CH ２ ) ２ NCO, Compound 143: Q is selected from the structures represented by Q2, and A ３ = O, R １ =CH(CH ３ ) ２ , R ２ =CH ３ , R ４ =CH ３ , R ５ =CH ３ , R ６ = (CH ３ CH ２ CH ２ ) ２ NCO, Compound 144: Q is selected from the structures represented by Q2, and A ３ = O, R １ =CH ３ , R ２ =CH ３ , R ４ = 、R ５ =CH ３ 、R ６ =(CH ３ CH ２ CH ２ ) ２ NCO、 Compound 145: Q is selected from the structures represented by Q2, and A ３ = S, R １ =CH ３ , R ２ =CH ３ , R ４ =CH ３ , R ５ =CH ３ , R ６ = (CH ３ OCH ２ CH ２ ) ２ NCO, Compound 146: Q is selected from the structures represented by Q2, and A ３ = S, R １ =CH ３ , R ２ =CH ３ , R ４ =CH ３ , R ５ =CH ３ , R ６ = 、 Compound 147: Q is selected from the structures represented by Q2, and A ３ = S, R １ =CH ３ , R ２ =CH ３ , R ４ =CH ３ , R ５ =CH ３ , R ６ = 、 Compound 148: Q is selected from the structures represented by Q2, and A ３ = S, R １ =CH ３ , R ２ =CH ３ , R ４ =CH ３ , R ５ =CH ３ , R ６ = 、 Compound 149: Q is selected from the structures represented by Q2, and A ３ = O, R １ =CH ３ , R ２ =CH ３ , R ４ =CH ３ , R ５ =CH ３ , R ６ = 、 Compound 150: Q is selected from the structures represented by Q2, and A ３ = O, R １ =CH ２ CH ３ , R ２ =CH ３ , R ４ =CH ３ , R ５ =CH ３ , R ６ = 、 Compound 151: Q is selected from the structures represented by Q2, and A ３ = O, R １ =CH(CH ３ ) ２ , R ２ =CH ３ , R ４ =CH ３ , R ５ =CH ３ , R ６ = 、 Compound 152: Q is selected from the structures represented by Q2, and A ３ = O, R １ =CH ３ , R ２ =CH ３ , R ４ = 、R ５ =CH ３ 、R ６ = 、 Compound 153: Q is selected from the structures represented by Q2, and A ３ = O, R １ =CH ２ CH ３ , R ２ =CH ３ , R ４ = 、R ５ =CH ３ 、R ６ = 、 Compound 154: Q is selected from the structures represented by Q2, and A ３ = O, R １ =CH ３ , R ２ =CH ３ , R ４ =CH ３ , R ５ =CH ３ , R ６ = 、 Compound 155: Q is selected from the structures represented by Q2, and A ３ = O, R １ =CH ２ CH ３ , R ２ =CH ３ , R ４ =CH ３ , R ５ =CH ３ , R ６ = 、 Compound 156: Q is selected from the structures represented by Q2, and A ３ = O, R １ =CH ２ CH ２ CH ３ , R ２ =CH ３ , R ４ =CH ３ , R ５ =CH ３ , R ６ = 、 Compound 157: Q is selected from the structures represented by Q2, and A ３ = O, R １ =CH(CH ３ ) ２ , R ２ =CH ３ , R ４ =CH ３ , R ５ =CH ３ , R ６ = 、 Compound 158: Q is selected from the structures represented by Q2, and A ３ = O, R １ =CH ３ , R ２ =CH ３ , R ４ = H, R ５ =CH ３ , R ６ = 、 Compound 159: Q is selected from the structures represented by Q2, and A ３ = O, R １ =CH ２ CH ３ , R ２ =CH ３ , R ４ = H, R ５ =CH ３ , R ６ = 、 Compound 160: Q is selected from the structures represented by Q2, and A ３ = O, R １ =CH ２ CH ２ CH ３ , R ２ =CH ３ , R ４ = H, R ５ =CH ３ , R ６ = 、 Compound 161: Q is selected from the structures represented by Q2, and A ３ = O, R １ =CH(CH ３ ) ２ , R ２ =CH ３ , R ４ = H, R ５ =CH ３ , R ６ = 、 Compound 162: Q is selected from the structures represented by Q2, and A ３ = O, R １ =CH ３ , R ２ =CH ３ , R ４ = 、R ５ =CH ３ 、R ６ = 、 Compound 163: Q is selected from the structures represented by Q2, and A ３ = O, R １ =CH ２ CH ３ , R ２ =CH ３ , R ４ = 、R ５ =CH ３ 、R ６ = 、 Compound 164: Q is selected from the structures represented by Q2, and A ３ = O, R １ =CH ２ CH ２ CH ３ , R ２ =CH ３ , R ４ = 、R ５ =CH ３ 、R ６ = 、 Compound 165: Q is selected from the structures represented by Q2, and A ３ = O, R １ =CH(CH ３ ) ２ , R ２ =CH ３ , R ４ = 、R ５ =CH ３ 、R ６ = 、 Compound 166: Q is selected from the structures represented by Q2, and A ３ = O, R １ =CH ３ , R ２ =CH ３ , R ４ =CH ３ , R ５ =CH ３ , R ６ = 、 Compound 167: Q is selected from the structures represented by Q2, and A ３ = O, R １ =CH ２ CH ３ , R ２ =CH ３ , R ４ =CH ３ , R ５ =CH ３ , R ６ = 、 Compound 168: Q is selected from the structures represented by Q2, and A ３ = O, R １ =CH ２ CH ２ CH ３ , R ２ =CH ３ , R ４ =CH ３ , R ５ =CH ３ , R ６ = 、 Compound 169: Q is selected from the structures represented by Q2, and A ３ = O, R １ =CH(CH ３ ) ２ , R ２ =CH ３ , R ４ =CH ３ , R ５ =CH ３ , R ６ = 、 Compound 170: Q is selected from the structures represented by Q2, and A ３ = O, R １ =CH ３ , R ２ =CH ３ , R ４ = H, R ５ =CH ３ , R ６ = 、 Compound 171: Q is selected from the structures represented by Q2, and A ３ = O, R １ =CH ２ CH ３ , R ２ =CH ３ , R ４ = H, R ５ =CH ３ , R ６ = 、 Compound 172: Q is selected from the structures represented by Q2, and A ３ = O, R １ =CH ２ CH ２ CH ３ , R ２ =CH ３ , R ４ = H, R ５ =CH ３ , R ６ = 、 Compound 173: Q is selected from the structures represented by Q2, and A ３ = O, R １ =CH(CH ３ ) ２ , R ２ =CH ３ , R ４ = H, R ５ =CH ３ , R ６ = 、 Compound 174: Q is selected from the structures represented by Q2, and A ３ = O, R １ =CH ３ , R ２ =CH ３ , R ４ = 、R ５ =CH ３ 、R ６ = 、 Compound 175: Q is selected from the structures represented by Q2, and A ３ = O, R １ =CH ２ CH ３ , R ２ =CH ３ , R ４ = 、R ５ =CH ３ 、R ６ = 、 Compound 176: Q is selected from the structures represented by Q2, and A ３ = O, R １ =CH ２ CH ２ CH ３ , R ２ =CH ３ , R ４ = 、R ５ =CH ３ 、R ６ = 、 Compound 177: Q is selected from the structures represented by Q2, and A ３ = O, R １ =CH(CH ３ ) ２ , R ２ =CH ３ , R ４ = 、R ５ =CH ３ 、R ６ = 、 Compound 178: Q is selected from the structures represented by Q2, and A ３ = O, R １ =CH ３ , R ２ =CH ３ , R ４ =CH ３ , R ５ =CH ３ , R ６ = 、 Compound 179: Q is selected from the structures represented by Q2, and A ３ = O, R １ =CH ２ CH ２ CH ３ , R ２ =CH ３ , R ４ =CH ３ , R ５ =CH ３ , R ６ = 、 Compound 180: Q is selected from the structures represented by Q2, and A ３ = O, R １ =CH ３ , R ２ =CH ３ , R ４ = H, R ５ =CH ３ , R ６ = 、 Compound 181: Q is selected from the structures represented by Q2, and A ３ = O, R １ =CH ２ CH ２ CH ３ , R ２ =CH ３ , R ４ = H, R ５ =CH ３ , R ６ = 、 Compound 182: Q is selected from the structures represented by Q2, and A ３ = O, R １ =CH ３ , R ２ =CH ３ , R ４ = 、R ５ =CH ３ 、R ６ = 、 Compound 183: Q is selected from the structures represented by Q2, and A ３ = O, R １ =CH ２ CH ２ CH ３ , R ２ =CH ３ , R ４ = 、R ５ =CH ３ 、R ６ = 、 Compound 184: Q is selected from the structures represented by Q2, and A ３ = O, R １ =CH ２ CH ３ , R ２ =CH ３ , R ４ =CH ３ , R ５ =CH ３ , R ６ = 、 Compound 185: Q is selected from the structures represented by Q2, and A ３ = O, R １ =CH(CH ３ ) ２ , R ２ =CH ３ , R ４ =CH ３ , R ５ =CH ３ , R ６ = 、 Compound 186: Q is selected from the structures represented by Q2, and A ３ = O, R １ =CH ２ CH ３ , R ２ =CH ３ , R ４ = H, R ５ =CH ３ , R ６ = 、 Compound 187: Q is selected from the structures represented by Q2, and A ３ = O, R １ =CH(CH ３ ) ２ , R ２ =CH ３ , R ４ = H, R ５ =CH ３ , R ６ = 、 Compound 188: Q is selected from the structures represented by Q2, and A ３ = O, R １ =CH ２ CH ３ , R ２ =CH ３ , R ４ = 、R ５ =CH ３ 、R ６ = 、 Compound 189: Q is selected from the structures represented by Q2, and A ３ = O, R １ =CH(CH ３ ) ２ , R ２ =CH ３ , R ４ = 、R ５ =CH ３ 、R ６ = 、 Compound 190: Q is selected from the structures represented by Q2, and A ３ = O, R １ =CH ２ CH ３ , R ２ =CH ３ , R ４ =CH ３ , R ５ =CH2CH ３ , R ６ = 、 Compound 191: Q is selected from the structures represented by Q2, and A ３ = O, R １ =CH ３ , R ２ =CH ３ , R ４ = H, R ５ =CH ２ CH ３ , R ６ = 、 Compound 192: Q is selected from the structures represented by Q2, and A ３ = O, R １ =CH ２ CH ２ CH ３ , R ２ =CH ３ , R ４ = 、R ５ =CH ２ CH ３ 、R ６ = 、 Compound 193: Q is selected from the structures represented by Q2, and A ３ = O, R １ =CH(CH ３ ) ２ , R ２ =CH ３ , R ４ = 、R ５ =CH ２ CH ３ 、R ６ = 、 Compound 194: Q is selected from the structures represented by Q2, and A ３ = O, R １ =CH ３ , R ２ =CH ３ , R ４ =CH ３ , R ５ =CH ３ , R ６ = 、 Compound 195: Q is selected from the structures represented by Q2, and A ３ = O, R １ =CH ２ CH ３ , R ２ =CH ３ , R ４ =CH ３ , R ５ =CH ３ , R ６ = 、 Compound 196: Q is selected from the structures represented by Q2, and A ３ = O, R １ =CH ２ CH ２ CH ３ , R ２ =CH ３ , R ４ =CH ３ , R ５ =CH ３ , R ６ = 、 Compound 197: Q is selected from the structures represented by Q2, and A ３ = O, R １ =CH(CH ３ ) ２ , R ２ =CH ３ , R ４ =CH ３ , R ５ =CH ３ , R ６ = 、 Compound 198: Q is selected from the structures represented by Q2, and A ３ = O, R １ =CH ３ , R ２ =CH ３ , R ４ = H, R ５ =CH ３ , R ６ = 、 Compound 199: Q is selected from the structures represented by Q2, and A ３ = O, R １ =CH ２ CH ３ , R ２ =CH ３ , R ４ = H, R ５ =CH ３ , R ６ = 、 Compound 200: Q is selected from the structures represented by Q2, and A ３ = O, R １ =CH(CH ３ ) ２ , R ２ =CH ３ , R ４ = H, R ５ =CH ３ , R ６ = 、 Compound 201: Q is selected from the structures represented by Q2, and A ３ = O, R １ =CH ３ , R ２ =CH ３ , R ４ = 、R ５ =CH ３ 、R ６ = 、 Compound 202: Q is selected from the structures represented by Q2, and A ３ = O, R １ =CH ２ CH ３ , R ２ =CH ３ , R ４ = 、R ５ =CH ３ 、R ６ = 、 Compound 203: Q is selected from the structures represented by Q2, and A ３ = O, R １ =CH(CH ３ ) ２ , R ２ =CH ３ , R ４ = 、R ５ =CH ３ 、R ６ = 、 Compound 204: Q is selected from the structures represented by Q2, and A ３ = O, R １ =CH ３ , R ２ =CH ３ , R ４ =CH ３ , R ５ =CH ３ , R ６ = 、 Compound 205: Q is selected from the structures represented by Q2, and A ３ = O, R １ =CH ２ CH ３ , R ２ =CH ３ , R ４ =CH ３ , R ５ =CH ３ , R ６ = 、 Compound 206: Q is selected from the structures represented by Q2, and A ３ = O, R １ =CH(CH ３ ) ２ , R ２ =CH ３ , R ４ =CH ３ , R ５ =CH ３ , R ６ = 、 Compound 207: Q is selected from the structures represented by Q2, and A ３ = O, R １ =CH ３ , R ２ =CH ３ , R ４ = H, R ５ =CH ３ , R ６ = 、 Compound 208: Q is selected from the structures represented by Q2, and A ３ = O, R １ =CH ２ CH ３ , R ２ =CH ３ , R ４ = H, R ５ =CH ３ , R ６ = 、 Compound 209: Q is selected from the structures represented by Q2, and A ３ = O, R １ =CH ２ CH ２ CH ３ , R ２ =CH ３ , R ４ = H, R ５ =CH ３ , R ６ = 、 Compound 210: Q is selected from the structures represented by Q2, and A ３ = O, R １ =CH(CH ３ ) ２ , R ２ =CH ３ , R ４ = H, R ５ =CH ３ , R ６ = 、 Compound 211: Q is selected from the structures represented by Q2, and A ３ = O, R １ =CH ２ CH ３ , R ２ =CH ３ , R ４ = 、R ５ =CH ３ 、R ６ = 、 Compound 212: Q is selected from the structures represented by Q2, and A ３ = O, R １ =CH(CH ３ ) ２ , R ２ =CH ３ , R ４ = 、R ５ =CH ３ 、R ６ = 、 Compound 213: Q is selected from the structures represented by Q2, and A ３ = O, R １ =CH ３ , R ２ =CH ３ , R ４ =CH ３ , R ５ =CH ３ , R ６ = 、 Compound 214: Q is selected from the structures represented by Q2, and A ３ = O, R １ =CH ２ CH ３ , R ２ =CH ３ , R ４ =CH ３ , R ５ =CH ３ , R ６ = 、 Compound 215: Q is selected from the structures represented by Q2, and A ３ = O, R １ =CH(CH ３ ) ２ , R ２ =CH ３ , R ４ =CH ３ , R ５ =CH ３ , R ６ = 、 Compound 216: Q is selected from the structures represented by Q2, and A ３ = O, R １ =CH ３ , R ２ =CH ３ , R ４ = 、R ５ =CH ３ 、R ６ = 、 Compound 217: Q is selected from the structures represented by Q2, and A ３ = O, R １ =CH(CH ３ ) ２ , R ２ =CH ３ , R ４ = 、R ５ =CH ３ 、R ６ = 、 Compound 218: Q is selected from the structures represented by Q2, and A ３ = O, R １ =CH ３ , R ２ =CH ３ , R ４ =CH ３ , R ５ =CH ３ , R ６ = 、 Compound 219: Q is selected from the structures represented by Q2, and A ３ = O, R １ =CH ２ CH ３ , R ２ =CH ３ , R ４ =CH ３ , R ５ =CH ３ , R ６ = 、 Compound 220: Q is selected from the structures represented by Q2, and A ３ = O, R １ =CH(CH ３ ) ２ , R ２ =CH ３ , R ４ =CH ３ , R ５ =CH ３ , R ６ = 、 Compound 221: Q is selected from the structures represented by Q2, and A ３ = O, R １ =CH ３ , R ２ =CH ３ , R ４ = 、R ５ =CH ３ 、R ６ = 、 Compound 222: Q is selected from the structures represented by Q2, and A ３ = O, R １ =CH(CH ３ ) ２ , R ２ =CH ３ , R ４ = 、R ５ =CH ３ 、R ６ = 、 Compound 223: Q is selected from the structures represented by Q2, and A ３ = O, R １ =CH ３ , R ２ =CH ３ , R ４ =CH ３ , R ５ =CH ３ , R ６ = 、 Compound 224: Q is selected from the structures represented by Q2, and A ３ = O, R １ =CH ２ CH ３ , R ２ =CH ３ , R ４ =CH ３ , R ５ =CH ３ , R ６ = 、 Compound 225: Q is selected from the structures represented by Q2, and A ３ = O, R １ =CH(CH ３ ) ２ , R ２ =CH ３ , R ４ =CH ３ , R ５ =CH ３ , R ６ = 、 Compound 226: Q is selected from the structures represented by Q2, and A ３ = O, R １ =CH(CH ３ ) ２ , R ２ =CH ３ , R ４ = 、R ５ =CH ３ 、R ６ = 、 Compound 227: Q is selected from the structures represented by Q2, and A ３ = O, R １ =CH ３ , R ２ =CH ３ , R ４ =CH ３ , R ５ =CH ３ , R ６ = 、 Compound 228: Q is selected from the structures represented by Q2, and A ３ = O, R １ =CH ２ CH ３ , R ２ =CH ３ , R ４ =CH ３ , R ５ =CH ３ , R ６ = 、 Compound 229: Q is selected from the structures represented by Q2, and A ３ = O, R １ =CH(CH ３ ) ２ , R ２ =CH ３ , R ４ =CH ３ , R ５ =CH ３ , R ６ = 、 Compound 230: Q is selected from the structures represented by Q2, and A ３ = O, R １ =CH(CH ３ ) ２ , R ２ =CH ３ , R ４ = 、R ５ =CH ３ 、R ６ = 、 Compound 231: Q is selected from the structures represented by Q2, and A ３ = O, R １ =CH ３ , R ２ =CH ３ , R ４ =CH ３ , R ５ =CH ３ , R ６ = 、 Compound 232: Q is selected from the structures represented by Q2, and A ３ = S, R １ =CH ３ , R ２ =CH ３ , R ４ =CH ３ , R ５ =CH ３ , R ６ = 、 Compound 233: Q is selected from the structures represented by Q2, and A ３ = O, R １ =CH ２ CH ３ , R ２ =CH ３ , R ４ =CH ３ , R ５ =CH ３ , R ６ = 、 Compound 234: Q is selected from the structures represented by Q2, and A ３ = O, R １ =CH(CH ３ ) ２ , R ２ =CH ３ , R ４ =CH ３ , R ５ =CH ３ , R ６ = 、 Compound 235: Q is selected from the structures represented by Q2, and A ３ = O, R １ =CH ３ , R ２ =CH ３ , R ４ = 、R ５ =CH ３ 、R ６ = 、 Compound 236: Q is selected from the structures represented by Q2, and A ３ = O, R １ =CH ２ CH ３ , R ２ =CH ３ , R ４ = 、R ５ =CH ３ 、R ６ = 、 Compound 237: Q is selected from the structures represented by Q2, and A ３ = O, R １ =CH(CH ３ ) ２ , R ２ =CH ３ , R ４ = 、R ５ =CH ３ 、R ６ = 、 Compound 238: Q is selected from the structures represented by Q2, and A ３ = O, R １ =CH ３ , R ２ =CH ３ , R ４ =CH ３ , R ５ =CH ３ , R ６ = 、 Compound 239: Q is selected from the structures represented by Q2, and A ３ = O, R １ =CH ２ CH ３ , R ２ =CH ３ , R ４ =CH ３ , R ５ =CH ３ , R ６ = 、 Compound 240: Q is selected from the structures represented by Q2, and A ３ = O, R １ =CH(CH ３ ) ２ , R ２ =CH ３ , R ４ =CH ３ , R ５ =CH ３ , R ６ = 、 Compound 241: Q is selected from the structures represented by Q2, and A ３ = O, R １ =CH ３ , R ２ =CH ３ , R ４ = 、R ５ =CH ３ 、R ６ = 、 Compound 242: Q is selected from the structures represented by Q2, and A ３ = O, R １ =CH ２ CH ３ , R ２ =CH ３ , R ４ = 、R ５ =CH ３ 、R ６ = 、 Compound 243: Q is selected from the structures represented by Q2, and A ３ = O, R １ =CH(CH ３ ) ２ , R ２ =CH ３ , R ４ = 、R ５ =CH ３ 、R ６ = 、 Compound 244: Q is selected from the structures represented by Q2, and A ３ = O, R １ =CH ３ , R ２ =CH ３ , R ４ =CH ３ , R ５ =CH ３ , R ６ = 、 Compound 245: Q is selected from the structures represented by Q2, and A ３ = S, R １ =CH ３ , R ２ =CH ３ , R ４ =CH ３ , R ５ =CH ３ , R ６ = 、 Compound 246: Q is selected from the structures represented by Q2, and A ３ = O, R １ =CH(CH ３ ) ２ , R ２ =CH ３ , R ４ =CH ３ , R ５ =CH ３ , R ６ = 、 Compound 247: Q is selected from the structures represented by Q2, and A ３ = O, R １ =CH ３ , R ２ =CH ３ , R ４ = 、R ５ =CH ３ 、R ６ = 、 Compound 248: Q is selected from the structures represented by Q2, and A ３ = O, R １ =CH ２ CH ３ , R ２ =CH ３ , R ４ = 、R ５ =CH ３ 、R ６ = 、 Compound 249: Q is selected from the structures represented by Q2, and A ３ = O, R １ =CH(CH ３ ) ２ , R ２ =CH ３ , R ４ = 、R ５ =CH ３ 、R ６ = 、 Compound 250: Q is selected from the structures represented by Q2, and A ３ = O, R １ =CH ３ , R ２ =CH ３ , R ４ =CH ３ , R ５ =CH ３ , R ６ = 、 Compound 251: Q is selected from the structures represented by Q2, and A ３ = O, R １ =CH(CH ３ ) ２ , R ２ =CH ３ , R ４ =CH ３ , R ５ =CH ３ , R ６ = 、 Compound 252: Q is selected from the structures represented by Q2, and A ３ = O, R １ =CH ３ , R ２ =CH ３ , R ４ = 、R ５ =CH ３ 、R ６ = 、 Compound 253: Q is selected from the structures represented by Q2, and A ３ = O, R １ =CH ２ CH ３ , R ２ =CH ３ , R ４ = 、R ５ =CH ３ 、R ６ = 、 Compound 254: Q is selected from the structures represented by Q2, and A ３ = O, R １ =CH(CH ３ ) ２ , R ２ =CH ３ , R ４ = 、R ５ =CH ３ 、R ６ = 、 Compound 255: Q is selected from the structures represented by Q2, and A ３ = O, R １ =CH ３ , R ２ =CH ３ , R ４ =CH ３ , R ５ =CH ３ , R ６ = 、 Compound 256: Q is selected from the structures represented by Q2, and A ３ = S, R １ =CH ３ , R ２ =CH ３ , R ４ =CH ３ , R ５ =CH ３ , R ６ = 、 Compound 257: Q is selected from the structures represented by Q2, and A ３ = O, R １ =CH(CH ３ ) ２ , R ２ =CH ３ , R ４ =CH ３ , R ５ =CH ３ , R ６ = 、 Compound 258: Q is selected from the structures represented by Q2, and A ３ = O, R １ =CH ３ , R ２ =CH ３ , R ４ = 、R ５ =CH ３ 、R ６ = 、 Compound 259: Q is selected from the structures represented by Q2, and A ３ = O, R １ =CH ２ CH ３ , R ２ =CH ３ , R ４ = 、R ５ =CH ３ 、R ６ = 、 Compound 260: Q is selected from the structures represented by Q2, and A ３ = O, R １ =CH(CH ３ ) ２ , R ２ =CH ３ , R ４ = 、R ５ =CH ３ 、R ６ = 2. The oxadiazolone compound or a tautomer thereof according to claim 1, wherein:

8. 8. Use of the oxadiazolone compound or its tautomer according to any one of claims 1 to 7 in weed control.

9. 9. The use according to claim 8, wherein the weeds are one or more species selected from broadleaf weeds and grass weeds.

10. A herbicidal composition comprising the oxadiazolone compound or a tautomer thereof according to any one of claims 1 to 7 and an adjuvant.

11. A method for controlling weeds, comprising applying to a crop the herbicidal composition of claim 10.

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