Oxadiazolone compound, weeding composition and application of oxadiazolone compound and weeding composition

Abstract

The invention provides an oxadiazolone compound, a weeding composition and application of the oxadiazolone compound and the weeding composition. The position between sulfonyl and C1 on a benzene ring of the benzoyl compound is substituted by the oxadiazolone group shown in the formula (a) to obtain the oxadiazolone compound, and the oxadiazolone compound not only has unexpected high herbicidal activity to various weeds, but also is relatively safe to various crops such as corn, rice and the like. Experimental results show that the compound provided by the invention has good herbicidal activity, can effectively control barnyard grass, digitaria sanguinalis, piemarker and other weeds at a low dosage, obtains a good herbicidal effect, and is safe to crops.

Description

Oxadiazolone compounds, herbicidal compositions and uses thereof

[0001] Cross-references

[0002] This application claims priority to the Chinese patent application filed on November 17, 2023, with application number 202311532732.0 and invention name “Oxadiazolone compounds, herbicidal compositions and uses thereof”, the entire contents of which are incorporated herein by reference. Technical Field

[0003] The present application relates to the technical field of herbicides, and in particular to an oxadiazolone compound, a herbicidal composition and uses thereof. Background Art

[0004] Studies have found that benzoyl compounds have herbicidal activity, and their structural modification and transformation can further improve their herbicidal activity. However, compounds with high herbicidal activity have low safety for crops. Therefore, obtaining compounds with both high herbicidal activity and high crop safety is one of the current research trends in benzoyl herbicides. Summary of the Invention

[0005] Purpose of the Invention

[0006] 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. The oxadiazolone compound provided in the present application has high herbicidal activity and crop safety.

[0007] Solution

[0008] The present application provides an oxadiazolone compound represented by formula (I) or its tautomer:

[0009] In formula (I), R1 and R2 are independently selected from C1-C6 alkyl or C3-C6 cycloalkyl groups which are unsubstituted or substituted by 1 to 3 groups independently selected from the following groups: halogen, nitro, C1-C6 alkyl, halogenated C1-C6 alkyl, C1-C6 alkoxy or halogenated C1-C6 alkoxy;

[0010] Q is selected from the structure represented by Q1, Q2 or Q3:

[0011] wherein A1, A2, A3, A4 and A5 are independently selected from O or S;

[0012] R3 and R 10independently selected from hydrogen, C1-C6 alkyl, C3-C6 cycloalkyl, C1-C6 alkoxy, phenyl or benzyl, which are unsubstituted or substituted by 1-3 groups independently selected from the following groups: halogen, nitro, C1-C6 alkyl, halo-substituted C1-C6 alkyl, C1-C6 alkoxy, halo-substituted C1-C6 alkoxy, phenyl or halo-substituted phenyl;

[0013] n is an integer from 1 to 6;

[0014] R4 is selected from hydrogen, halogen, C1-C6 alkyl, C3-C6 cycloalkyl or C1-C6 alkoxy which is unsubstituted or substituted by 1 to 3 groups independently selected from the following groups: halogen, nitro, C1-C6 alkyl, halogenated C1-C6 alkyl, C1-C6 alkoxy or halogenated C1-C6 alkoxy;

[0015] R5 is selected from hydrogen, C1-C6 alkyl or C3-C6 cycloalkyl which is unsubstituted or substituted by 1 to 3 groups independently selected from the following groups: halogen, nitro, C1-C6 alkyl, halogenated C1-C6 alkyl, C1-C6 alkoxy or halogenated C1-C6 alkoxy;

[0016] R6 is selected from hydrogen, the structure represented by formula (1), C1-C6 alkyl, C3-C6 cycloalkyl, C3-C8 heterocycloalkyl, which is unsubstituted or substituted by 1-3 groups independently selected from the following groups: halogen, nitro, C1-C6 alkyl, halogenated C1-C6 alkyl, C1-C6 alkoxy, or halogenated C1-C6 alkoxy;

[0017] In formula (1), A6 is selected from N or CR9, and R9 is selected from hydrogen, C1-C6 alkyl, C3-C6 cycloalkyl, or C1-C6 alkoxy, which is unsubstituted or substituted by 1 to 3 groups independently selected from the following groups: halogen, nitro, C1-C6 alkyl, halogenated C1-C6 alkyl, C1-C6 alkoxy, or halogenated C1-C6 alkoxy;

[0018] R7 and R8 are independently selected from hydrogen, C1-C6 alkyl, C3-C6 cycloalkyl or C1-C6 alkoxy which is unsubstituted or substituted by 1-3 groups independently selected from the following groups: halogen, nitro, C1-C6 alkyl, halogenated C1-C6 alkyl, C1-C6 alkoxy or halogenated C1-C6 alkoxy; R7 and R8 are not H at the same time;

[0019] Alternatively, R7, R8 and A6 where they are located form a C3-C8 ring that is unsubstituted or substituted by 1 to 3 groups independently selected from the following groups and contains 0 to 3 heteroatoms: halogen, nitro, C1-C6 alkyl, C3-C6 cycloalkyl, halogenated C1-C6 alkyl, C1-C6 alkoxy or halogenated C1-C6 alkoxy; the heteroatoms are selected from oxygen, sulfur or nitrogen.

[0020] The applicant has discovered that oxadiazolone compounds obtained by replacing the position between the sulfonyl group and Cl on the benzene ring of benzoyl compounds with a group of formula (a) not only have excellent herbicidal activity against various weeds, but are also relatively safe for various crops such as corn and rice:

[0021] group.

[0022] In some specific implementations, in formula (I), R1 and R2 are independently selected from C1-C4 alkyl or C3-C6 cycloalkyl, which are unsubstituted or substituted with 1-3 groups independently selected from the following groups: halogen, nitro, C1-C4 alkyl, halogenated C1-C4 alkyl, C1-C4 alkoxy or halogenated C1-C4 alkoxy; in some specific implementations, R1 and R2 are independently selected from -CH3, -CH2CH3, -CH2CH2CH3, -CH(CH 3)2, -C(CH3)3, -CH2CH2CH2CH3, -CF3, -CH2CF3, -CH2CH2CF3, -CH(CF3)2, -C(CF3)3, -CHCH3CF3, -C(CH3)2CF3 or CCH2(CF3)2; in some specific implementations, R1 is selected from methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl or tert-butyl; R2 is selected from methyl, ethyl, n-propyl, tert-butyl or trifluoromethyl.

[0023] In some specific implementations, Q is selected from the structure shown in Q1:

[0024] Wherein, A1 and A2 are independently selected from O or S. In some specific implementations, A1 and A2 are both O.

[0025] In the Q1 structure, R3 is preferably selected from hydrogen, C1-C4 alkyl, which is unsubstituted or substituted by 1 to 3 groups independently selected from the following groups: C3-C6 cycloalkyl, C1-C4 alkoxy, phenyl or benzyl: halogen, nitro, C1-C4 alkyl, halogenated C1-C4 alkyl, C1-C4 alkoxy, halogenated C1-C4 alkoxy, phenyl or halogenated phenyl; in some specific implementations, R3 is selected from hydrogen, C1-C4 alkyl, phenyl, which is unsubstituted or substituted by 1 to 3 halogens, or benzyl, which is unsubstituted or substituted by 1 to 3 halogens; in some specific implementations, 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.

[0026] In the Q1 structure, n is the number of substituents R3, which is an integer from 1 to 6, and can be 1, 2, 3, 4, 5 or 6, and is preferably 1, 2 or 3.

[0027] In some specific implementations, Q is selected from the structure shown in Q2:

[0028] In the Q2 structure, A3 is selected from O or S. In some specific implementations, A3 is O.

[0029] In the Q2 structure, R4 is preferably selected from hydrogen, halogen, C1-C4 alkyl, C3-C6 cycloalkyl, or C1-C4 alkoxy, which is unsubstituted or substituted with 1-3 groups independently selected from the following groups: halogen, nitro, C1-C4 alkyl, halogenated C1-C4 alkyl, C1-C4 alkoxy, or halogenated C1-C4 alkoxy. In some specific embodiments, R4 is selected from hydrogen, halogen, C1-C4 alkyl, halogenated C1-C4 alkyl, C3-C6 cycloalkyl, or C1-C4 alkoxy. In some specific embodiments, R4 is selected from hydrogen, chlorine, C1-C4 alkyl, or C3-C6 cycloalkyl. In some specific embodiments, R4 is selected from hydrogen, methyl, ethyl, isopropyl, or cyclopropyl.

[0030] In the Q2 structure, R5 is preferably selected from hydrogen, C1-C4 alkyl or C3-C6 cycloalkyl which is unsubstituted or substituted by 1 to 3 groups independently selected from the following groups: halogen, nitro, C1-C4 alkyl, halogenated C1-C4 alkyl, C1-C4 alkoxy or halogenated C1-C4 alkoxy; in some specific implementations, R5 is selected from hydrogen, C1-C4 alkyl, halogenated C1-C4 alkyl or C3-C6 cycloalkyl; in some specific implementations, R5 is selected from methyl, ethyl or cyclopropyl.

[0031] In the Q2 structure, R6 is preferably selected from hydrogen, the structure shown in formula (1), a C1-C4 alkyl group that is unsubstituted or substituted by 1 to 3 groups independently selected from the following groups: halogen, nitro, C1-C4 alkyl group, halogenated C1-C4 alkyl group, C1-C4 alkoxy group or halogenated C1-C4 alkoxy group; in some specific implementations, R6 is selected from hydrogen, the structure shown in formula (1), a C1-C4 alkyl group, a C3-C6 cycloalkyl group, a C3-C8 heterocycloalkyl group or a halogenated C1-C4 alkyl group.

[0032] In formula (1), A6 is selected from N or CR9, and R9 is selected from hydrogen, C1-C6 alkyl, C3-C6 cycloalkyl, or C1-C6 alkoxy, which is unsubstituted or substituted with 1-3 groups independently selected from the following groups: halogen, nitro, C1-C6 alkyl, halogenated C1-C6 alkyl, C1-C6 alkoxy, or halogenated 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.

[0033] In formula (1), R7 and R8 are independently selected from hydrogen, C1-C6 alkyl, C3-C6 cycloalkyl, or C1-C6 alkoxy, which is unsubstituted or substituted with 1-3 groups independently selected from the following groups: halogen, nitro, C1-C6 alkyl, halogenated C1-C6 alkyl, C1-C6 alkoxy, or halogenated C1-C6 alkoxy; in some specific embodiments, 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 embodiments, 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 H at the same time.

[0034] In formula (1), R7 and R8 preferably form a C3-C8 ring with their A6, which is unsubstituted or substituted by 1-3 groups independently selected from the following groups, and contains 1-3 heteroatoms: halogen, nitro, C1-C4 alkyl, C3-C6 cycloalkyl, halogenated C1-C4 alkyl, C1-C4 alkoxy, or halogenated C1-C4 alkoxy; the heteroatoms are selected from oxygen, sulfur, or nitrogen. In some specific implementations, R7 and R8 preferably form a heterocyclic ring, pyrazole ring, furan ring, tetrahydrofuran ring, thiophene ring, or tetrahydrothiophene ring with their A6, which is unsubstituted or substituted by 1-3 groups independently selected from the following groups: halogen, nitro, C1-C4 alkyl, C3-C6 cycloalkyl, halogenated C1-C4 alkyl, C1-C4 alkoxy, or halogenated C1-C4 alkoxy. In some specific implementations, R7 and R8 preferably form a ring with A6 where they are located as shown in the following structure:

[0035] Among them, R 1 、R 3 、R 4 、R 6R is independently selected from hydrogen, halogen, C1-C4 alkyl, halogenated C1-C4 alkyl or C3-C6 cycloalkyl, preferably selected from hydrogen, chlorine, trifluoromethyl, methyl, ethyl, isopropyl or cyclopropyl. 2 、R 5 、R 7 Independently selected from hydrogen, C1-C4 alkyl, halogenated C1-C4 alkyl or C3-C6 cycloalkyl, preferably selected from hydrogen, methyl, ethyl or cyclopropyl.

[0036] In some specific implementations, R6 is preferably selected from the following structures:

[0037] Among them, R 1 、R 3 、R 4 、R 6 R is independently selected from hydrogen, halogen, C1-C4 alkyl, halogenated C1-C4 alkyl or C3-C6 cycloalkyl; preferably selected from hydrogen, chlorine, trifluoromethyl, methyl, ethyl, isopropyl or cyclopropyl. 2 、R 5 、R 7 Independently selected from hydrogen, C1-C4 alkyl, halogenated C1-C4 alkyl or C3-C6 cycloalkyl, preferably selected from hydrogen, methyl, ethyl or cyclopropyl.

[0038] In some specific implementations, Q is selected from the structure shown in Q3:

[0039] In the Q3 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.

[0040] In the Q3 structure, R 10 is preferably selected from hydrogen, C1-C4 alkyl, C3-C6 cycloalkyl, C1-C4 alkoxy, phenyl or benzyl, which are unsubstituted or substituted by 1-3 groups independently selected from the following groups: halogen, nitro, C1-C4 alkyl, halogenated C1-C4 alkyl, C1-C4 alkoxy, halogenated C1-C4 alkoxy, phenyl or halogenated phenyl; in some specific implementations, R 10 is selected from hydrogen, C1-C4 alkyl, phenyl which is unsubstituted or substituted by 1-3 halogens, or benzyl which is unsubstituted or substituted by 1-3 halogens; 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. In some specific implementations, R 10Selected from H, -CH3, -CH2CH3, -CH2CH2CH3, -CH(CH3)2, -C(CH3)3, -CH2CH2CH2CH3, phenyl, chlorophenyl, dichlorophenyl, C6H5CH2-, C6H4ClCH2- or C6H3Cl2CH2-.

[0041] In some specific implementations, Q is selected from the structure shown in Q1-1:

[0042] R3 is selected from H, C1-C4 alkyl or C1-C4 halogenated alkyl.

[0043] In some specific implementations, Q is selected from the structure shown in Q3-1:

[0044] R 10 Selected from H, C1-C4 alkyl, C1-C4 haloalkyl, phenyl, halophenyl, C1-C4 alkyl substituted with phenyl or C1-C4 alkyl substituted with halophenyl.

[0045] In some specific implementations, Q is selected from the structure shown in Q2-1:

[0046] X1 is selected from C or N, X2 is selected from C, N, O or S, and X1 and X2 are not C at the same time;

[0047] R 11 is selected from H, halogen, C1-C4 alkyl, C3-C6 cycloalkyl or C1-C4 haloalkyl; in some specific implementations, R 11 Selected from H, CH3, CF3, -CH2CH 3、 Cyclopropyl or Cl.

[0048] m is a substituent R 11 The number of is an integer from 1 to 3;

[0049] R4 is selected from hydrogen, halogen, C1-C4 alkyl, halogenated C1-C4 alkyl, C3-C6 cycloalkyl, halogenated C3-C6 cycloalkyl, C1-C4 alkoxy, halogenated C1-C4 alkoxy;

[0050] R5 is selected from hydrogen, C1-C4 alkyl or halogenated C1-C4 alkyl.

[0051] In some specific implementations, the compound is selected from the following:

[0052] Compound 1: Q is selected from the structure shown in Q1-1, R1=CH3, R2=CH3, R3=H;

[0053] Compound 2: Q is selected from the structure shown in Q1-1, R1=CH3, R2=CH2CH3, R3=H;

[0054] Compound 3: Q is selected from the structure shown in Q1-1, R1=CH3, R2=CH2CH2CH3, R3=H;

[0055] Compound 4: Q is selected from the structure shown in Q1-1, R1=CH3, R2=C(CH3)3, R3=H;

[0056] Compound 5: Q is selected from the structure shown in Q1-1, R1=CH3, R2=CF3, R3=H;

[0057] Compound 6: Q is selected from the structure shown in Q1-1, R1=CH2CH3, R2=CH3, R3=H;

[0058] Compound 7: Q is selected from the structure shown in Q1-1, R1=CH2CH3, R2=CH2CH3, R3=H;

[0059] Compound 8: Q is selected from the structure shown in Q1-1, R1=CH2CH3, R2=CH2CH2CH3, R3=H;

[0060] Compound 9: Q is selected from the structure shown in Q1-1, R1=CH2CH3, R2=C(CH3)3, R3=H;

[0061] Compound 10: Q is selected from the structure shown in Q1-1, R1=CH2CH3, R2=CF3, R3=H;

[0062] Compound 11: Q is selected from the structure shown in Q1-1, R1=CH2CH2CH3, R2=CH3, R3=H;

[0063] Compound 12: Q is selected from the structure shown in Q1-1, R1=CH2CH2CH3, R2=CH2CH3, R3=H;

[0064] Compound 13: Q is selected from the structure shown in Q1-1, R1=CH2CH2CH3, R2=CH2CH2CH3, R3=H;

[0065] Compound 14: Q is selected from the structure shown in Q1-1, R1=CH2CH2CH3, R2=C(CH3)3, R3=H;

[0066] Compound 15: Q is selected from the structure shown in Q1-1, R1=CH2CH2CH3, R2=CF3, R3=H;

[0067] Compound 16: Q is selected from the structure shown in Q1-1, R1=CH(CH3)2, R2=CH3, R3=H;

[0068] Compound 17: Q is selected from the structure shown in Q1-1, R1=CH(CH3)2, R2=CH2CH3, R3=H;

[0069] Compound 18: Q is selected from the structure shown in Q1-1, R1=CH(CH3)2, R2=CH2CH2CH3, R3=H;

[0070] Compound 19: Q is selected from the structure shown in Q1-1, R1=CH(CH3)2, R2=C(CH3)3, R3=H;

[0071] Compound 20: Q is selected from the structure shown in Q1-1, R1=CH(CH3)2, R2=CF3, R3=H;

[0072] Compound 21: Q is selected from the structure shown in Q1-1, R1=CH2CH2CH2CH3, R2=CH3, R3=H;

[0073] Compound 22: Q is selected from the structure shown in Q1-1, R1=CH2CH2CH2CH3, R2=CH2CH3, R3=H;

[0074] Compound 23: Q is selected from the structure shown in Q1-1, R1=CH2CH2CH2CH3, R2=CH2CH2CH3, R3=H;

[0075] Compound 24: Q is selected from the structure shown in Q1-1, R1=CH2CH2CH2CH3, R2=C(CH3)3, R3=H;

[0076] Compound 25: Q is selected from the structure shown in Q1-1, R1=CH2CH2CH2CH3, R2=CF3, R3=H;

[0077] Compound 26: Q is selected from the structure shown in Q1-1, R1=C(CH3)3, R2=CH3, R3=H;

[0078] Compound 27: Q is selected from the structure shown in Q1-1, R1=C(CH3)3, R2=CH2CH3, R3=H;

[0079] Compound 28: Q is selected from the structure shown in Q1-1, R1=C(CH3)3, R2=CH2CH2CH3, R3=H;

[0080] Compound 29: Q is selected from the structure shown in Q1-1, R1=C(CH3)3, R2=C(CH3)3, R3=H;

[0081] Compound 30: Q is selected from the structure shown in Q1-1, R1=C(CH3)3, R2=CF3, R3=H;

[0082] Compound 31: Q is selected from the structure shown in Q3, R1=CH3, R2=CH3, A4=O, A5=O, R 10 =CH3;

[0083] Compound 32: Q is selected from the structure shown in Q3, R1=CH3, R2=CH3, A4=O, A5=O, R 10 =CH2CH3;

[0084] Compound 33: Q is selected from the structure shown in Q3, R1=CH3, R2=CH3, A4=O, A5=O, R 10 =CH2CH2CH3;

[0085] Compound 34: Q is selected from the structure shown in Q3, R1=CH3, R2=CH3, A4=O, A5=O, R 10 =CH(CH3)2;

[0086] Compound 35: Q is selected from the structure shown in Q3, R1=CH3, R2=CH3, A4=O, A5=O, R 10 =CH2CH2CH2CH3;

[0087] Compound 36: Q is selected from the structure shown in Q3, R1=CH3, R2=CH3, A4=O, A5=O, R 10 =C(CH3)3;

[0088] Compound 37: Q is selected from the structure shown in Q3, R1=CH3, R2=CH3, A4=O, A5=O,

[0089] Compound 38: Q is selected from the structure shown in Q3, R1=CH3, R2=CH3, A4=O, A5=O,

[0090] Compound 39: Q is selected from the structure shown in Q3, R1=CH3, R2=CH3, A4=O, A5=O,

[0091] Compound 40: Q is selected from the structure shown in Q3, R1=CH3, R2=CH3, A4=O, A5=O,

[0092] Compound 41: Q is selected from the structure shown in Q3, R1=CH3, R2=CH3, A4=O, A5=O,

[0093] Compound 42: Q is selected from the structure shown in Q3, R1=CH3, R2=CH3, A4=O, A5=O,

[0094] Compound 43: Q is selected from the structure shown in Q3, R1=CH3, R2=CH3, A4=O, A5=O,

[0095] Compound 44: Q is selected from the structure shown in Q3, R1=CH3, R2=CH3, A4=O, A5=S, R 10 =CH3;

[0096] Compound 45: Q is selected from the structure shown in Q3, R1=CH3, R2=CH3, A4=O, A5=S, R 10 =CH2CH3;

[0097] Compound 46: Q is selected from the structure shown in Q3, R1=CH3, R2=CH3, A4=O, A5=S, R 10 =CH2CH2CH3;

[0098] Compound 47: Q is selected from the structure shown in Q3, R1=CH3, R2=CH3, A4=O, A5=S, R 10 =CH(CH3)2;

[0099] Compound 48: Q is selected from the structure shown in Q3, R1=CH3, R2=CH3, A4=O, A5=S, R 10 =CH2CH2CH2CH3;

[0100] Compound 49: Q is selected from the structure shown in Q3, R1=CH3, R2=CH3, A4=O, A5=S, R 10 =C(CH3)3;

[0101] Compound 50: Q is selected from the structure shown in Q3, R1=CH3, R2=CH3, A4=O, A5=S,

[0102] Compound 51: Q is selected from the structure shown in Q3, R1=CH3, R2=CH3, A4=O, A5=S,

[0103] Compound 52: Q is selected from the structure shown in Q3, R1=CH3, R2=CH3, A4=O, A5=S,

[0104] Compound 53: Q is selected from the structure shown in Q3, R1=CH3, R2=CH3, A4=O, A5=S,

[0105] Compound 54: Q is selected from the structure shown in Q3, R1=CH3, R2=CH3, A4=O, A5=S,

[0106] Compound 55: Q is selected from the structure shown in Q3, R1=CH3, R2=CH3, A4=O, A5=S,

[0107] Compound 56: Q is selected from the structure shown in Q2, A3=O, R1=CH3, R2=CH3, R4=H, R5=CH3, R6=H;

[0108] Compound 57: Q is selected from the structure shown in Q2, A3=O, R1=CH3, R2=CH3, R4=H, R5=CH2CH3, R6=H;

[0109] Compound 58: Q is selected from the structure shown in Q2, A3=O, R1=CH3, R2=CH3, R4=CH3, R5=CH3, R6=H;

[0110] Compound 59: Q is selected from the structure shown in Q2, A3=O, R1=CH3, R2=CH3, R4=CH3, R5=CH2CH3, R6=H;

[0111] Compound 60: Q is selected from the structure shown in Q2, A3=O, R1=CH3, R2=CH3, R4=CH2CH3, R5=CH3, R6=H;

[0112] Compound 61: Q is selected from the structure shown in Q2, A3=O, R1=CH3, R2=CH3, R4=CH2CH3, R5=CH2CH3, R6=H;

[0113] Compound 62: Q is selected from the structure shown in Q2, A3=O, R1=CH3, R2=CH3, R4=CH2CH2CH3, R5=CH3, R6=H;

[0114] Compound 63: Q is selected from the structure shown in Q2, A3=O, R1=CH3, R2=CH3, R4=CH2CH2CH3, R5=CH2CH3, R6=H;

[0115] Compound 64: Q is selected from the structure shown in Q2, A3=O, R1=CH3, R2=CH3, R4=CH(CH3)2, R5=CH3, R6=H;

[0116] Compound 65: Q is selected from the structure shown in Q2, A3=O, R1=CH3, R2=CH3, R4=CH(CH3)2, R5=CH2CH3, R6=H;

[0117] Compound 66: Q is selected from the structure shown in Q2, A3=O, R1=CH3, R2=CH3, R4=CF3, R5=CH3, R6=H;

[0118] Compound 67: Q is selected from the structure shown in Q2, A3=O, R1=CH3, R2=CH3, R4=CF3, R5=CH2CH3, R6=H;

[0119] Compound 68: Q is selected from the structure shown in Q2, A3=O, R1=CH3, R2=CH3, R5=CH3,R6=H;

[0120] Compound 69: Q is selected from the structure shown in Q2, A3=O, R1=CH3, R2=CH3, R5=CH2CH3,R6=H;

[0121] Compound 70: Q is selected from the structure shown in Q2, A3=O, R1=CH2CH3, R2=CH3, R4=H, R5=CH3, R6=H;

[0122] Compound 71: Q is selected from the structure shown in Q2, A3=O, R1=CH2CH3, R2=CH3, R4=H, R5=CH2CH3, R6=H;

[0123] Compound 72: Q is selected from the structure shown in Q2, A3=O, R1=CH2CH3, R2=CH3, R4=CH3, R5=CH3, R6=H;

[0124] Compound 73: Q is selected from the structure shown in Q2, A3=O, R1=CH2CH3, R2=CH3, R4=CH3, R5=CH2CH3, R6=H;

[0125] Compound 74: Q is selected from the structure shown in Q2, A3=O, R1=CH2CH3, R2=CH3, R4=CH2CH3, R5=CH3, R6=H;

[0126] Compound 75: Q is selected from the structure shown in Q2, A3=O, R1=CH2CH3, R2=CH3, R4=CH2CH3, R5=CH2CH3, R6=H;

[0127] Compound 76: Q is selected from the structure shown in Q2, A3=O, R1=CH2CH3, R2=CH3, R4=CH2CH2CH3, R5=CH3, R6=H;

[0128] Compound 77: Q is selected from the structure shown in Q2, A3=O, R1=CH2CH3, R2=CH3, R4=CH2CH2CH3, R5=CH2CH3, R6=H;

[0129] Compound 78: Q is selected from the structure shown in Q2, A3=O, R1=CH2CH3, R2=CH3, R4=CH(CH3)2, R5=CH3, R6=H;

[0130] Compound 79: Q is selected from the structure shown in Q2, A3=O, R1=CH2CH3, R2=CH3, R4=CH(CH3)2, R5=CH2CH3, R6=H;

[0131] Compound 80: Q is selected from the structure shown in Q2, A3=O, R1=CH2CH3, R2=CH3, R4=CF3, R5=CH3, R6=H;

[0132] Compound 81: Q is selected from the structure shown in Q2, A3=O, R1=CH2CH3, R2=CH3, R4=CF3, R5=CH2CH3, R6=H;

[0133] Compound 82: Q is selected from the structure shown in Q2, A3=O, R1=CH2CH3, R2=CH3, R5=CH3,R6=H;

[0134] Compound 83: Q is selected from the structure shown in Q2, A3=O, R1=CH2CH3, R2=CH3, R5=CH2CH3,R6=H;

[0135] Compound 84: Q is selected from the structure shown in Q2, A3=O, R1=CH2CH2CH3, R2=CH3, R4=H, R5=CH3, R6=H;

[0136] Compound 85: Q is selected from the structure shown in Q2, A3=O, R1=CH2CH2CH3, R2=CH3, R4=H, R5=CH2CH3, R6=H;

[0137] Compound 86: Q is selected from the structure shown in Q2, A3=O, R1=CH2CH2CH3, R2=CH3, R4=CH3, R5=CH3, R6=H;

[0138] Compound 87: Q is selected from the structure shown in Q2, A3=O, R1=CH2CH2CH3, R2=CH3, R4=CH3, R5=CH2CH3, R6=H;

[0139] Compound 88: Q is selected from the structure shown in Q2, A3=O, R1=CH2CH2CH3, R2=CH3, R4=CH2CH3, R5=CH3, R6=H;

[0140] Compound 89: Q is selected from the structure shown in Q2, A3=O, R1=CH2CH2CH3, R2=CH3, R4=CH2CH3, R5=CH2CH3, R6=H;

[0141] Compound 90: Q is selected from the structure shown in Q2, A3=O, R1=CH2CH2CH3, R2=CH3, R4=CH2CH2CH3, R5=CH3, R6=H;

[0142] Compound 91: Q is selected from the structure shown in Q2, A3=O, R1=CH2CH2CH3, R2=CH3, R4=CH2CH2CH3, R5=CH2CH3, R6=H;

[0143] Compound 92: Q is selected from the structure shown in Q2, A3=O, R1=CH2CH2CH3, R2=CH3, R4=CH(CH3)2, R5=CH3, R6=H;

[0144] Compound 93: Q is selected from the structure shown in Q2, A3=O, R1=CH2CH2CH3, R2=CH3, R4=CH(CH3)2, R5=CH2CH3, R6=H;

[0145] Compound 94: Q is selected from the structure shown in Q2, A3=O, R1=CH2CH2CH3, R2=CH3, R4=CF3, R5=CH3, R6=H;

[0146] Compound 95: Q is selected from the structure shown in Q2, A3=O, R1=CH2CH2CH3, R2=CH3, R4=CF3, R5=CH2CH3, R6=H;

[0147] Compound 96: Q is selected from the structure shown in Q2, A3=O, R1=CH2CH2CH3, R2=CH3, R5=CH3,R6=H;

[0148] Compound 97: Q is selected from the structure shown in Q2, A3=O, R1=CH2CH2CH3, R2=CH3, R5=CH2CH3,R6=H;

[0149] Compound 98: Q is selected from the structure shown in Q2, A3=O, R1=CH(CH3)2, R2=CH3, R4=H, R5=CH3, R6=H;

[0150] Compound 99: Q is selected from the structure shown in Q2, A3=O, R1=CH(CH3)2, R2=CH3, R4=H, R5=CH2CH3, R6=H;

[0151] Compound 100: Q is selected from the structure shown in Q2, A3=O, R1=CH(CH3)2, R2=CH3, R4=CH3, R5=CH3, R6=H;

[0152] Compound 101: Q is selected from the structure shown in Q2, A3=O, R1=CH(CH3)2, R2=CH3, R4=CH3, R5=CH2CH3, R6=H;

[0153] Compound 102: Q is selected from the structure shown in Q2, A3=O, R1=CH(CH3)2, R2=CH3, R4=CH2CH3, R5=CH3, R6=H;

[0154] Compound 103: Q is selected from the structure shown in Q2, A3=O, R1=CH(CH3)2, R2=CH3, R4=CH2CH3, R5=CH2CH3, R6=H;

[0155] Compound 104: Q is selected from the structure shown in Q2, A3=O, R1=CH(CH3)2, R2=CH3, R4=CH2CH2CH3, R5=CH3, R6=H;

[0156] Compound 105: Q is selected from the structure shown in Q2, A3=O, R1=CH(CH3)2, R2=CH3, R4=CH2CH2CH3, R5=CH2CH3, R6=H;

[0157] Compound 106: Q is selected from the structure shown in Q2, A3=O, R1=CH(CH3)2, R2=CH3, R4=CH(CH3)2, R5=CH3, R6=H;

[0158] Compound 107: Q is selected from the structure shown in Q2, A3=O, R1=CH(CH3)2, R2=CH3, R4=CH(CH3)2, R5=CH2CH3, R6=H;

[0159] Compound 108: Q is selected from the structure shown in Q2, A3=O, R1=CH(CH3)2, R2=CH3, R4=CF3, R5=CH3, R6=H;

[0160] Compound 109: Q is selected from the structure shown in Q2, A3=O, R1=CH(CH3)2, R2=CH3, R4=CF3, R5=CH2CH3, R6=H;

[0161] Compound 110: Q is selected from the structure shown in Q2, A3=O, R1=CH(CH3)2, R2=CH3, R5=CH3,R6=H;

[0162] Compound 111: Q is selected from the structure shown in Q2, A3=O, R1=CH(CH3)2, R2=CH3, R5=CH2CH3,R6=H;

[0163] Compound 112: Q is selected from the structure shown in Q2, A3=O, R1=CH2CH2CH2CH3, R2=CH3, R4=H, R5=CH3, R6=H;

[0164] Compound 113: Q is selected from the structure shown in Q2, A3=O, R1=CH2CH2CH2CH3, R2=CH3, R4=H, R5=CH2CH3, R6=H;

[0165] Compound 114: Q is selected from the structure shown in Q2, A3=O, R1=CH2CH2CH2CH3, R2=CH3, R4=CH3, R5=CH3, R6=H;

[0166] Compound 115: Q is selected from the structure shown in Q2, A3=O, R1=CH2CH2CH2CH3, R2=CH3, R4=CH3, R5=CH2CH3, R6=H;

[0167] Compound 116: Q is selected from the structure shown in Q2, A3=O, R1=CH2CH2CH2CH3, R2=CH3, R4=CH2CH3, R5=CH3, R6=H;

[0168] Compound 117: Q is selected from the structure shown in Q2, A3=O, R1=CH2CH2CH2CH3, R2=CH3, R4=CH2CH3, R5=CH2CH3, R6=H;

[0169] Compound 118: Q is selected from the structure shown in Q2, A3=O, R1=CH2CH2CH2CH3, R2=CH3, R4=CH2CH2CH3, R5=CH3, R6=H;

[0170] Compound 119: Q is selected from the structure shown in Q2, A3=O, R1=CH2CH2CH2CH3, R2=CH3, R4=CH2CH2CH3, R5=CH2CH3, R6=H;

[0171] Compound 120: Q is selected from the structure shown in Q2, A3=O, R1=CH2CH2CH2CH3, R2=CH3, R4=CH(CH3)2, R5=CH3, R6=H;

[0172] Compound 121: Q is selected from the structure shown in Q2, A3=O, R1=CH2CH2CH2CH3, R2=CH3, R4=CH(CH3)2, R5=CH2CH3, R6=H;

[0173] Compound 122: Q is selected from the structure shown in Q2, A3=O, R1=CH2CH2CH2CH3, R2=CH3, R4=CF3, R5=CH3, R6=H;

[0174] Compound 123: Q is selected from the structure shown in Q2, A3=O, R1=CH2CH2CH2CH3, R2=CH3, R4=CF3, R5=CH2CH3, R6=H;

[0175] Compound 124: Q is selected from the structure shown in Q2, A3=O, R1=CH2CH2CH2CH3, R2=CH3, R5=CH3,R6=H;

[0176] Compound 125: Q is selected from the structure shown in Q2, A3=O, R1=CH2CH2CH2CH3, R2=CH3, R5=CH2CH3,R6=H;

[0177] Compound 126: Q is selected from the structure shown in Q2, A3=O, R1=C(CH3)3, R2=CH3, R4=H, R5=CH3, R6=H;

[0178] Compound 127: Q is selected from the structure shown in Q2, A3=O, R1=C(CH3)3, R2=CH3, R4=H, R5=CH2CH3, R6=H;

[0179] Compound 128: Q is selected from the structure shown in Q2, A3=O, R1=C(CH3)3, R2=CH3, R4=CH3, R5=CH3, R6=H;

[0180] Compound 129: Q is selected from the structure shown in Q2, A3=O, R1=C(CH3)3, R2=CH3, R4=CH3, R5=CH2CH3, R6=H;

[0181] Compound 130: Q is selected from the structure shown in Q2, A3=O, R1=C(CH3)3, R2=CH3, R4=CH2CH3, R5=CH3, R6=H;

[0182] Compound 131: Q is selected from the structure shown in Q2, A3=O, R1=C(CH3)3, R2=CH3, R4=CH2CH3, R5=CH2CH3, R6=H;

[0183] Compound 132: Q is selected from the structure shown in Q2, A3=O, R1=C(CH3)3, R2=CH3, R4=CH2CH2CH3, R5=CH3, R6=H;

[0184] Compound 133: Q is selected from the structure shown in Q2, A3=O, R1=C(CH3)3, R2=CH3, R4=CH2CH2CH3, R5=CH2CH3, R6=H;

[0185] Compound 134: Q is selected from the structure shown in Q2, A3=O, R1=C(CH3)3, R2=CH3, R4=CH(CH3)2, R5=CH3, R6=H;

[0186] Compound 135: Q is selected from the structure shown in Q2, A3=O, R1=C(CH3)3, R2=CH3, R4=CH(CH3)2, R5=CH2CH3, R6=H;

[0187] Compound 136: Q is selected from the structure shown in Q2, A3=O, R1=C(CH3)3, R2=CH3, R4=CF3, R5=CH3, R6=H;

[0188] Compound 137: Q is selected from the structure shown in Q2, A3=O, R1=C(CH3)3, R2=CH3, R4=CF3, R5=CH2CH3, R6=H;

[0189] Compound 138: Q is selected from the structure shown in Q2, A3=O, R1=C(CH3)3, R2=CH3, R5=CH3,R6=H;

[0190] Compound 139: Q is selected from the structure shown in Q2, A3=O, R1=C(CH3)3, R2=CH3, R5=CH2CH3,R6=H;

[0191] Compound 140: Q is selected from the structure shown in Q2, A3=S, R1=CH3, R2=CH3, R4=CH3, R5=CH3, R6=(CH3CH2)2NCO;

[0192] Compound 141: Q is selected from the structure shown in Q2, A3=O, R1=CH3, R2=CH3, R4=CH3, R5=CH3, R6=(CH3CH2CH2)2NCO;

[0193] Compound 142: Q is selected from the structure shown in Q2, A3=O, R1=CH2CH3, R2=CH3, R4=CH3, R5=CH3, R6=(CH3CH2CH2)2NCO;

[0194] Compound 143: Q is selected from the structure shown in Q2, A3=O, R1=CH(CH3)2, R2=CH3, R4=CH3, R5=CH3, R6=(CH3CH2CH2)2NCO;

[0195] Compound 144: Q is selected from the structure shown in Q2, A3=O, R1=CH3, R2=CH3, R5=CH3, R6=(CH3CH2CH2)2NCO;

[0196] Compound 145: Q is selected from the structure shown in Q2, A3=S, R1=CH3, R2=CH3, R4=CH3, R5=CH3, R6=(CH3OCH2CH2)2NCO;

[0197] Compound 146: Q is selected from the structure shown in Q2, A3=S, R1=CH3, R2=CH3, R4=CH3, R5=CH3,

[0198] Compound 147: Q is selected from the structure shown in Q2, A3=S, R1=CH3, R2=CH3, R4=CH3, R5=CH3,

[0199] Compound 148: Q is selected from the structure shown in Q2, A3=S, R1=CH3, R2=CH3, R4=CH3, R5=CH3,

[0200] Compound 149: Q is selected from the structure shown in Q2, A3=O, R1=CH3, R2=CH3, R4=CH3, R5=CH3,

[0201] Compound 150: Q is selected from the structure shown in Q2, A3=O, R1=CH2CH3, R2=CH3, R4=CH3, R5=CH3,

[0202] Compound 151: Q is selected from the structure shown in Q2, A3=O, R1=CH(CH3)2, R2=CH3, R4=CH3, R5=CH3,

[0203] Compound 152: Q is selected from the structure shown in Q2, A3=O, R1=CH3, R2=CH3, R5=CH3,

[0204] Compound 153: Q is selected from the structure shown in Q2, A3=O, R1=CH2CH3, R2=CH3, R5=CH3,

[0205] Compound 154: Q is selected from the structure shown in Q2, A3=O, R1=CH3, R2=CH3, R4=CH3, R5=CH3,

[0206] Compound 155: Q is selected from the structure shown in Q2, A3=O, R1=CH2CH3, R2=CH3, R4=CH3, R5=CH3,

[0207] Compound 156: Q is selected from the structure shown in Q2, A3=O, R1=CH2CH2CH3, R2=CH3, R4=CH3, R5=CH3,

[0208] Compound 157: Q is selected from the structure shown in Q2, A3=O, R1=CH(CH3)2, R2=CH3, R4=CH3, R5=CH3,

[0209] Compound 158: Q is selected from the structure shown in Q2, A3=O, R1=CH3, R2=CH3, R4=H, R5=CH3,

[0210] Compound 159: Q is selected from the structure shown in Q2, A3=O, R1=CH2CH3, R2=CH3, R4=H, R5=CH3,

[0211] Compound 160: Q is selected from the structure shown in Q2, A3=O, R1=CH2CH2CH3, R2=CH3, R4=H, R5=CH3,

[0212] Compound 161: Q is selected from the structure shown in Q2, A3=O, R1=CH(CH3)2, R2=CH3, R4=H, R5=CH3,

[0213] Compound 162: Q is selected from the structure shown in Q2, A3=O, R1=CH3, R2=CH3, R5=CH3,

[0214] Compound 163: Q is selected from the structure shown in Q2, A3=O, R1=CH2CH3, R2=CH3, R5=CH3,

[0215] Compound 164: Q is selected from the structure shown in Q2, A3=O, R1=CH2CH2CH3, R2=CH3, R5=CH3,

[0216] Compound 165: Q is selected from the structure shown in Q2, A3=O, R1=CH(CH3)2, R2=CH3, R5=CH3,

[0217] Compound 166: Q is selected from the structure shown in Q2, A3=O, R1=CH3, R2=CH3, R4=CH3, R5=CH3,

[0218] Compound 167: Q is selected from the structure shown in Q2, A3=O, R1=CH2CH3, R2=CH3, R4=CH3, R5=CH3,

[0219] Compound 168: Q is selected from the structure shown in Q2, A3=O, R1=CH2CH2CH3, R2=CH3, R4=CH3, R5=CH3,

[0220] Compound 169: Q is selected from the structure shown in Q2, A3=O, R1=CH(CH3)2, R2=CH3, R4=CH3, R5=CH3,

[0221] Compound 170: Q is selected from the structure shown in Q2, A3=O, R1=CH3, R2=CH3, R4=H, R5=CH3,

[0222] Compound 171: Q is selected from the structure shown in Q2, A3=O, R1=CH2CH3, R2=CH3, R4=H, R5=CH3,

[0223] Compound 172: Q is selected from the structure shown in Q2, A3=O, R1=CH2CH2CH3, R2=CH3, R4=H, R5=CH3,

[0224] Compound 173: Q is selected from the structure shown in Q2, A3=O, R1=CH(CH3)2, R2=CH3, R4=H, R5=CH3,

[0225] Compound 174: Q is selected from the structure shown in Q2, A3=O, R1=CH3, R2=CH3, R5=CH3,

[0226] Compound 175: Q is selected from the structure shown in Q2, A3=O, R1=CH2CH3, R2=CH3, R5=CH3,

[0227] Compound 176: Q is selected from the structure shown in Q2, A3=O, R1=CH2CH2CH3, R2=CH3, R5=CH3,

[0228] Compound 177: Q is selected from the structure shown in Q2, A3=O, R1=CH(CH3)2, R2=CH3, R5=CH3,

[0229] Compound 178: Q is selected from the structure shown in Q2, A3=O, R1=CH3, R2=CH3, R4=CH3, R5=CH3,

[0230] Compound 179: Q is selected from the structure shown in Q2, A3=O, R1=CH2CH2CH3, R2=CH3, R4=CH3, R5=CH3,

[0231] Compound 180: Q is selected from the structure shown in Q2, A3=O, R1=CH3, R2=CH3, R4=H, R5=CH3,

[0232] Compound 181: Q is selected from the structure shown in Q2, A3=O, R1=CH2CH2CH3, R2=CH3, R4=H, R5=CH3,

[0233] Compound 182: Q is selected from the structure shown in Q2, A3=O, R1=CH3, R2=CH3, R5=CH3,

[0234] Compound 183: Q is selected from the structure shown in Q2, A3=O, R1=CH2CH2CH3, R2=CH3, R5=CH3,

[0235] Compound 184: Q is selected from the structure shown in Q2, A3=O, R1=CH2CH3, R2=CH3, R4=CH3, R5=CH3,

[0236] Compound 185: Q is selected from the structure shown in Q2, A3=O, R1=CH(CH3)2, R2=CH3, R4=CH3, R5=CH3,

[0237] Compound 186: Q is selected from the structure shown in Q2, A3=O, R1=CH2CH3, R2=CH3, R4=H, R5=CH3,

[0238] Compound 187: Q is selected from the structure shown in Q2, A3=O, R1=CH(CH3)2, R2=CH3, R4=H, R5=CH3,

[0239] Compound 188: Q is selected from the structure shown in Q2, A3=O, R1=CH2CH3, R2=CH3, R5=CH3,

[0240] Compound 189: Q is selected from the structure shown in Q2, A3=O, R1=CH(CH3)2, R2=CH3, R5=CH3,

[0241] Compound 190: Q is selected from the structure shown in Q2, A3=O, R1=CH2CH3, R2=CH3, R4=CH3, R5=CH2CH3,

[0242] Compound 191: Q is selected from the structure shown in Q2, A3=O, R1=CH3, R2=CH3, R4=H, R5=CH2CH3,

[0243] Compound 192: Q is selected from the structure shown in Q2, A3=O, R1=CH2CH2CH3, R2=CH3, R5=CH2CH3,

[0244] Compound 193: Q is selected from the structure shown in Q2, A3=O, R1=CH(CH3)2, R2=CH3, R5=CH2CH3,

[0245] Compound 194: Q is selected from the structure shown in Q2, A3=O, R1=CH3, R2=CH3, R4=CH3, R5=CH3,

[0246] Compound 195: Q is selected from the structure shown in Q2, A3=O, R1=CH2CH3, R2=CH3, R4=CH3, R5=CH3,

[0247] Compound 196: Q is selected from the structure shown in Q2, A3=O, R1=CH2CH2CH3, R2=CH3, R4=CH3, R5=CH3,

[0248] Compound 197: Q is selected from the structure shown in Q2, A3=O, R1=CH(CH3)2, R2=CH3, R4=CH3, R5=CH3,

[0249] Compound 198: Q is selected from the structure shown in Q2, A3=O, R1=CH3, R2=CH3, R4=H, R5=CH3,

[0250] Compound 199: Q is selected from the structure shown in Q2, A3=O, R1=CH2CH3, R2=CH3, R4=H, R5=CH3,

[0251] Compound 200: Q is selected from the structure shown in Q2, A3=O, R1=CH(CH3)2, R2=CH3, R4=H, R5=CH3,

[0252] Compound 201: Q is selected from the structure shown in Q2, A3=O, R1=CH3, R2=CH3, R5=CH3,

[0253] Compound 202: Q is selected from the structure shown in Q2, A3=O, R1=CH2CH3, R2=CH3, R5=CH3,

[0254] Compound 203: Q is selected from the structure shown in Q2, A3=O, R1=CH(CH3)2, R2=CH3, R5=CH3,

[0255] Compound 204: Q is selected from the structure shown in Q2, A3=O, R1=CH3, R2=CH3, R4=CH3, R5=CH3,

[0256] Compound 205: Q is selected from the structure shown in Q2, A3=O, R1=CH2CH3, R2=CH3, R4=CH3, R5=CH3,

[0257] Compound 206: Q is selected from the structure shown in Q2, A3=O, R1=CH(CH3)2, R2=CH3, R4=CH3, R5=CH3,

[0258] Compound 207: Q is selected from the structure shown in Q2, A3=O, R1=CH3, R2=CH3, R4=H, R5=CH3,

[0259] Compound 208: Q is selected from the structure shown in Q2, A3=O, R1=CH2CH3, R2=CH3, R4=H, R5=CH3,

[0260] Compound 209: Q is selected from the structure shown in Q2, A3=O, R1=CH2CH2CH3, R2=CH3, R4=H, R5=CH3,

[0261] Compound 210: Q is selected from the structure shown in Q2, A3=O, R1=CH(CH3)2, R2=CH3, R4=H, R5=CH3,

[0262] Compound 211: Q is selected from the structure shown in Q2, A3=O, R1=CH2CH3, R2=CH3, R5=CH3,

[0263] Compound 212: Q is selected from the structure shown in Q2, A3=O, R1=CH(CH3)2, R2=CH3, R5=CH3,

[0264] Compound 213: Q is selected from the structure shown in Q2, A3=O, R1=CH3, R2=CH3, R4=CH3, R5=CH3,

[0265] Compound 214: Q is selected from the structure shown in Q2, A3=O, R1=CH2CH3, R2=CH3, R4=CH3, R5=CH3,

[0266] Compound 215: Q is selected from the structure shown in Q2, A3=O, R1=CH(CH3)2, R2=CH3, R4=CH3, R5=CH3,

[0267] Compound 216: Q is selected from the structure shown in Q2, A3=O, R1=CH3, R2=CH3, R5=CH3,

[0268] Compound 217: Q is selected from the structure shown in Q2, A3=O, R1=CH(CH3)2, R2=CH3, R5=CH3,

[0269] Compound 218: Q is selected from the structure shown in Q2, A3=O, R1=CH3, R2=CH3, R4=CH3, R5=CH3,

[0270] Compound 219: Q is selected from the structure shown in Q2, A3=O, R1=CH2CH3, R2=CH3, R4=CH3, R5=CH3,

[0271] Compound 220: Q is selected from the structure shown in Q2, A3=O, R1=CH(CH3)2, R2=CH3, R4=CH3, R5=CH3,

[0272] Compound 221: Q is selected from the structure shown in Q2, A3=O, R1=CH3, R2=CH3, R5=CH3,

[0273] Compound 222: Q is selected from the structure shown in Q2, A3=O, R1=CH(CH3)2, R2=CH3, R5=CH3,

[0274] Compound 223: Q is selected from the structure shown in Q2, A3=O, R1=CH3, R2=CH3, R4=CH3, R5=CH3,

[0275] Compound 224: Q is selected from the structure shown in Q2, A3=O, R1=CH2CH3, R2=CH3, R4=CH3, R5=CH3,

[0276] Compound 225: Q is selected from the structure shown in Q2, A3=O, R1=CH(CH3)2, R2=CH3, R4=CH3, R5=CH3,

[0277] Compound 226: Q is selected from the structure shown in Q2, A3=O, R1=CH(CH3)2, R2=CH3, R5=CH3,

[0278] Compound 227: Q is selected from the structure shown in Q2, A3=O, R1=CH3, R2=CH3, R4=CH3, R5=CH3,

[0279] Compound 228: Q is selected from the structure shown in Q2, A3=O, R1=CH2CH3, R2=CH3, R4=CH3, R5=CH3,

[0280] Compound 229: Q is selected from the structure shown in Q2, A3=O, R1=CH(CH3)2, R2=CH3, R4=CH3, R5=CH3,

[0281] Compound 230: Q is selected from the structure shown in Q2, A3=O, R1=CH(CH3)2, R2=CH3, R5=CH3,

[0282] Compound 231: Q is selected from the structure shown in Q2, A3=O, R1=CH3, R2=CH3, R4=CH3, R5=CH3,

[0283] Compound 232: Q is selected from the structure shown in Q2, A3=S, R1=CH3, R2=CH3, R4=CH3, R5=CH3,

[0284] Compound 233: Q is selected from the structure shown in Q2, A3=O, R1=CH2CH3, R2=CH3, R4=CH3, R5=CH3,

[0285] Compound 234: Q is selected from the structure shown in Q2, A3=O, R1=CH(CH3)2, R2=CH3, R4=CH3, R5=CH3,

[0286] Compound 235: Q is selected from the structure shown in Q2, A3=O, R1=CH3, R2=CH3, R5=CH3,

[0287] Compound 236: Q is selected from the structure shown in Q2, A3=O, R1=CH2CH3, R2=CH3, R5=CH3,

[0288] Compound 237: Q is selected from the structure shown in Q2, A3=O, R1=CH(CH3)2, R2=CH3, R5=CH3,

[0289] Compound 238: Q is selected from the structure shown in Q2, A3=O, R1=CH3, R2=CH3, R4=CH3, R5=CH3,

[0290] Compound 239: Q is selected from the structure shown in Q2, A3=O, R1=CH2CH3, R2=CH3, R4=CH3, R5=CH3,

[0291] Compound 240: Q is selected from the structure shown in Q2, A3=O, R1=CH(CH3)2, R2=CH3, R4=CH3, R5=CH3,

[0292] Compound 241: Q is selected from the structure shown in Q2, A3=O, R1=CH3, R2=CH3, R5=CH3,

[0293] Compound 242: Q is selected from the structure shown in Q2, A3=O, R1=CH2CH3, R2=CH3, R5=CH3,

[0294] Compound 243: Q is selected from the structure shown in Q2, A3=O, R1=CH(CH3)2, R2=CH3, R5=CH3,

[0295] Compound 244: Q is selected from the structure shown in Q2, A3=O, R1=CH3, R2=CH3, R4=CH3, R5=CH3,

[0296] Compound 245: Q is selected from the structure shown in Q2, A3=S, R1=CH3, R2=CH3, R4=CH3, R5=CH3,

[0297] Compound 246: Q is selected from the structure shown in Q2, A3=O, R1=CH(CH3)2, R2=CH3, R4=CH3, R5=CH3,

[0298] Compound 247: Q is selected from the structure shown in Q2, A3=O, R1=CH3, R2=CH3, R5=CH3,

[0299] Compound 248: Q is selected from the structure shown in Q2, A3=O, R1=CH2CH3, R2=CH3, R5=CH3,

[0300] Compound 249: Q is selected from the structure shown in Q2, A3=O, R1=CH(CH3)2, R2=CH3, R5=CH3,

[0301] Compound 250: Q is selected from the structure shown in Q2, A3=O, R1=CH3, R2=CH3, R4=CH3, R5=CH3,

[0302] Compound 251: Q is selected from the structure shown in Q2, A3=O, R1=CH(CH3)2, R2=CH3, R4=CH3, R5=CH3,

[0303] Compound 252: Q is selected from the structure shown in Q2, A3=O, R1=CH3, R2=CH3, R5=CH3,

[0304] Compound 253: Q is selected from the structure shown in Q2, A3=O, R1=CH2CH3, R2=CH3, R5=CH3,

[0305] Compound 254: Q is selected from the structure shown in Q2, A3=O, R1=CH(CH3)2, R2=CH3, R5=CH3,

[0306] Compound 255: Q is selected from the structure shown in Q2, A3=O, R1=CH3, R2=CH3, R4=CH3, R5=CH3,

[0307] Compound 256: Q is selected from the structure shown in Q2, A3=S, R1=CH3, R2=CH3, R4=CH3, R5=CH3,

[0308] Compound 257: Q is selected from the structure shown in Q2, A3=O, R1=CH(CH3)2, R2=CH3, R4=CH3, R5=CH3,

[0309] Compound 258: Q is selected from the structure shown in Q2, A3=O, R1=CH3, R2=CH3, R5=CH3,

[0310] Compound 259: Q is selected from the structure shown in Q2, A3=O, R1=CH2CH3, R2=CH3, R5=CH3,

[0311] Compound 260: Q is selected from the structure shown in Q2, A3=O, R1=CH(CH3)2, R2=CH3, R5=CH3,

[0312] The compound of formula I or its tautomer of the present application has herbicidal activity and can be used to control various weeds in agriculture.

[0313] The present application also provides the use of the oxadiazolone compounds or their tautomers described in the above technical solution in controlling weeds.

[0314] In some specific implementations, the weeds are selected from one or more of broadleaf weeds or grass weeds.

[0315] In some specific implementations, the weeds are selected from one or more of velvetleaf, nightshade, crabgrass, and barnyard grass.

[0316] This application also provides a herbicidal composition comprising the oxadiazolone compound or its tautomer described in the above technical solution and an excipient. The application does not specifically limit the choice of excipient; the appropriate excipient may be selected based on the desired dosage form. The compound of formula I or its tautomer as the active ingredient may be present in an amount of 0.1 to 99% by weight, preferably 0.5 to 50% by weight.

[0317] The herbicidal compositions of the present application can be applied in a variety of formulations. Typically, the compounds of the present application are dissolved or dispersed in a carrier to prepare formulations that facilitate dispersion when used as herbicides. For example, these chemical formulations can be formulated as wettable powders or emulsifiable concentrates. Therefore, these compositions require at least one liquid or solid carrier, and typically require the addition of a suitable surfactant.

[0318] The present application also provides a method for controlling weeds, comprising: applying the herbicidal composition described in the above technical solution to crops.

[0319] Specifically, the present application applies a herbicidally effective amount of the herbicidal composition of the present application to the weeds or to the surface of the locus or growth medium where the weeds grow. A more suitable effective dose is 1 to 1000 grams per hectare, with a preferred effective dose being 10 to 500 grams per hectare. For certain applications, one or more other herbicides may be added to the herbicidal composition of the present application to produce additional advantages and effects. Beneficial effects

[0320] The applicant has substituted the sulfonyl group and Cl group on the benzene ring of a benzoyl compound with an oxadiazolone group represented by formula (a), resulting in an oxadiazolone compound that not only exhibits unexpectedly high herbicidal activity against a variety of weeds but is also relatively safe for crops such as corn and rice. Experimental results demonstrate that the compound provided by this application exhibits strong herbicidal activity, effectively controlling weeds such as barnyardgrass, crabgrass, and velvetleaf at low doses, achieving excellent weed control while remaining relatively safe for crops.

[0321] group. DETAILED DESCRIPTION

[0322] To make the purpose, technical solutions, and advantages of the embodiments of this application more clear, the technical solutions in the embodiments of this application will be clearly and completely described below. Obviously, the described embodiments are part of the embodiments of this application, not all of them. Based on the embodiments of this application, all other embodiments obtained by ordinary technicians in this field without making creative efforts are within the scope of protection of this application.

[0323] In addition, in order to better illustrate the present application, numerous specific details are provided in the following detailed description. It should be understood by those skilled in the art that the present application can be implemented without certain specific details. In some embodiments, raw materials, components, methods, means, etc. well known to those skilled in the art are not described in detail in order to highlight the main purpose of the present application.

[0324] In this application, the terms used are generally defined as follows:

[0325] Halogen: refers to fluorine, chlorine, bromine or iodine.

[0326] Alkyl: a straight-chain or branched alkyl group, such as methyl, ethyl, propyl, isopropyl, n-butyl or tert-butyl.

[0327] Cycloalkyl: a substituted or unsubstituted cyclic alkyl group, such as cyclopropyl, cyclopentyl or cyclohexyl, with substituents such as methyl, halogen, etc.

[0328] Haloalkyl: a straight-chain or branched alkyl group, in which the hydrogen atoms may be partially or completely replaced by halogen atoms, for example, chloromethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl or trifluoromethyl.

[0329] Alkoxy: A straight or branched chain alkyl group attached to the structure via an oxygen atom.

[0330] Haloalkoxy refers to a straight-chain or branched alkoxy group, in which the hydrogen atoms may be partially or completely replaced by halogen atoms, for example, chloromethoxy, dichloromethoxy, trichloromethoxy, fluoromethoxy, difluoromethoxy or trifluoromethoxy.

[0331] Alkylamino: A straight or branched chain alkyl group is attached to the structure via a nitrogen atom.

[0332] Haloalkylamino refers to a straight-chain or branched alkylamino group, in which the hydrogen atoms may be partially or completely substituted by halogen atoms.

[0333] Cycloalkylamino: A substituted or unsubstituted cyclic alkylamino group attached to the structure via the nitrogen atom, for example, cyclopentylamino or cyclohexylamino.

[0334] Heterocycle: A cyclic hydrocarbon containing heteroatoms such as N, O, or S. Examples include furan, thiophene, morpholine, cycloheximide, pyrazole, and piperidine.

[0335] Heterocyclic amino: The heterocyclic ring is attached to the structure through the nitrogen atom.

[0336] Tautomers: refer to structural isomers with different energies that can be converted into each other through a low energy barrier. If tautomerism is possible (such as in solution), chemical equilibrium of the tautomers can be achieved. For example, proton tautomers include interconversions through proton migration, such as keto-enol isomerization and imine-enamine isomerization. In this application, keto-enol interconversion occurs depending on external conditions (such as solvent, pH, etc.).

[0337] Some of the compounds of the present application can be illustrated by the specific compounds listed in Table 1, Table 2 and Table 3, but the present application is not limited to these compounds.

[0338] Table 1 Specific compounds 1 to 30

[0339] Table 2 Specific compounds 31 to 55

[0340] Table 3 Specific compounds 56-260

[0341] The molecular formula, mass spectrum, nuclear magnetic hydrogen spectrum and carbon spectrum data of some compounds are shown in Table 4:

[0342] Table 4 Molecular formula, mass spectrum, H NMR spectrum and C NMR spectrum data of some compounds

[0343] The compound of the general formula (I-3) of the present application can be prepared by the following method:

[0344] In the above formula, the compound of formula II and R 10 A5H is reacted in a base and a suitable solvent at a temperature between -10°C and boiling point for 0.5 to 24 hours to obtain a compound of formula I-3. The suitable solvent is selected from acetonitrile, DMF, HMPA, dimethyl sulfoxide, or tetrahydrofuran. The suitable base is selected from sodium hydrogen phosphate, sodium carbonate, potassium carbonate, or triethylamine.

[0345] The preparation method of the compound of formula II is as follows:

[0346] The compound of formula III in the above formula is reacted with a suitable chlorinating agent at 0°C to boiling point for 0.5 to 4 hours to obtain the compound of formula II. The suitable chlorinating agent is selected from thionyl chloride, oxalyl chloride or phosphorus trichloride.

[0347] The preparation method of the compound of formula III is as follows:

[0348] In the above formula, 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, or dimethyl sulfoxide. Suitable bases include sodium carbonate, potassium carbonate, or triethylamine. Suitable catalysts include sodium carbonate, potassium carbonate, or acetone cyanohydrin.

[0349] The preparation method of the compound of formula IV is as follows:

[0350] In the formula, the compound of formula V is first reacted with an acyl 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 produce the corresponding acyl chloride. The acyl 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 acyl chloride produced above is then reacted with 1,3-cyclohexanedione in the same or different solvent in the presence of a suitable base at a temperature between -10°C and the boiling point of the corresponding solvent for 0.5 to 24 hours to produce the compound of formula IV. The suitable base is selected from triethylamine, pyridine, sodium carbonate, potassium carbonate, sodium methoxide, or potassium tert-butoxide.

[0351] The preparation method of the compound of formula V is as follows:

[0352] The compound of formula VI (see Synthesis of cornfield herbicide tampronone in Pesticides, 2017, 56(5): 326-327, 379) and the compound of formula VII (commercially available product) are reacted in the presence of a suitable solvent and a base at a temperature of 0°C to the boiling point of the suitable solvent for 0.5 to 24 hours to obtain the compound of formula V. The suitable solvent is selected from acetonitrile, N,N-dimethylformamide, dimethyl sulfoxide, methanol, ethanol or isopropanol. The suitable base is selected from sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium methoxide or potassium tert-butoxide.

[0353] The preparation method of the compound of formula I-2 is as follows:

[0354] The compound of formula VIII in the above formula is reacted with the compound of formula R6Cl in a suitable solvent under the action of a base for 0.5 to 24 hours to obtain the compound of formula I-2. The suitable solvent is selected from dichloromethane, 1,2-dichloroethane, chloroform, carbon tetrachloride, benzene, toluene, acetonitrile, tetrahydrofuran, or dioxane. The suitable base is selected from sodium carbonate, potassium carbonate, or triethylamine.

[0355] Taking A3 as O as an example, the preparation method of the compound of formula VIII is as follows:

[0356] The reaction conditions for preparing the compound of formula VIII from the compound of formula V and formula IX refer to the reaction conditions for preparing the compound of formula III from formula IV, which will not be repeated in this application.

[0357] The compound of formula I-1 and the compound of formula III are tautomers due to different environmental conditions, for example, keto-enol interconversion occurs due to solvent, pH, etc.

[0358] The herbicidal composition, oxadiazolone compounds and uses thereof provided in the present application are further described below with reference to the examples.

[0359] Example 1 Synthesis of Compound 1

[0360] (1) Synthesis of 2-chloro-3-[(5-methyl-2-oxo-1,3,4-oxadiazol-3(2H)yl)methyl]-4-methylsulfonylbenzoic acid

[0361] 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) were added to a reaction flask. The temperature was raised to reflux for 3 hours. The solvent was evaporated under reduced pressure. Water (30 ml) was added with stirring and the pH was adjusted to 2-3 with 10% dilute hydrochloric acid. White crystals slowly precipitated, which were filtered and dried to obtain 4.8 g of white solid with a yield of 70%.

[0362] (2) 2-Chloro-3-[(5-methyl-2-oxo-1,3,4-oxadiazol-3(2H)yl)methyl]-4-methanesulfonylbenzoate (3-oxocyclohex-1-ene)

[0363] To a reaction flask, 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) were added, followed by the slow addition of thionyl chloride (14.3 g, 120 mmol). The mixture was heated at reflux for 4 hours. The solvent and excess thionyl chloride were evaporated under reduced pressure, followed by the addition of dichloromethane (60 mL) and 1,3-cyclohexanedione (2.3 g, 20.5 mmol). Triethylamine (3.2 g, 32 mmol) was then added dropwise. The mixture was stirred at room temperature for 1 hour, followed by the addition of water (50 mL). The aqueous phase was extracted twice with dichloromethane (30 mL x 2). The oily phases were combined and the solvent evaporated to yield 8.3 g of a light yellow solid, which was used directly in the next step.

[0364] (3) Synthesis of Compound 1 (2-{2-chloro-3-[(5-methyl-2-oxo-1,3,4-oxadiazol-3(2H)yl)methyl]-4-methylsulfonylbenzoyl}-1,3-cyclohexanedione)

[0365] To the reaction flask were added dichloromethane (60 ml), triethylamine (2.4 g, 24 mmol), and 2 drops of acetone cyanohydrin. 8.3 g of the solid obtained in the previous step was added and stirred at room temperature overnight. Water (60 ml) was added and stirred for half an hour. The pH was adjusted to 7-8 with 10% dilute hydrochloric acid. The aqueous phase was extracted twice with ethyl acetate (60 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 8.1 g of a light yellow solid with a purity of 97%.

[0366] Example 2 Synthesis of Compound 53

[0367] (1) 3-{2-chloro-3-[(2-chloro-6-oxocyclohex-1-enyl)carbonyl]-6-(methylsulfonyl)benzyl}-5-methyl-1,3,4-oxadiazol-2(3H)-ol

[0368] To a reaction flask were added 2-{2-chloro-3-[(5-methyl-2-oxo-1,3,4-oxadiazol-3(2H)yl)methyl]-4-methylsulfonylbenzoyl}-1,3-cyclohexanedione (8.8 g, 20 mmol) and dichloromethane (50 ml). Then, thionyl chloride (4.7 g, 40 mmol) was slowly added. The mixture was stirred at room temperature for 4 hours. The solvent and excess thionyl chloride were evaporated under reduced pressure to obtain 8.2 g of a yellow solid with a purity of 96%.

[0369] (2) Synthesis of Compound 53 (3-{2-chloro-3-[(2-benzylthio-6-oxocyclohex-1-enyl)carbonyl]-6-(methylsulfonyl)benzyl}-5-methyl-1,3,4-oxadiazol-2(3H)-alkane)

[0370] A 100 ml four-necked flask was added with 3-{2-chloro-3-[(2-chloro-6-oxocyclohex-1-enyl)carbonyl]-6-(methylsulfonyl)benzyl}-5-methyl-1,3,4-oxadiazol-2(3H)-alkane (6 g, 13 mmol), 30 g HMPA, and 1.6 g benzyl mercaptan. The mixture was stirred evenly and cooled to 0°C. 0.38 g of sodium hydrogen hydride was slowly added to the four-necked flask in batches. The sample was measured until the reaction of the raw materials was completed. The pH value was adjusted to 3 with acid water, and the mixture was extracted with ethyl acetate. The ethyl acetate phase was collected and rotary evaporated under reduced pressure to obtain a crude product. The product was stirred overnight with a dichloromethane and sodium bicarbonate aqueous solution. The dichloromethane phase was collected and rotary evaporated to obtain 5.6 g of a yellow solid with a purity of 90%.

[0371] Example 3 Synthesis of Compound 100

[0372] (1) Synthesis of 2-chloro-3-[(5-methyl-2-oxo-1,3,4-oxadiazol-3(2H)yl)methyl]-4-isopropylsulfonylbenzoic acid

[0373] To a reaction flask were added 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 temperature was raised to reflux for 3 hours, and the solvent was evaporated under reduced pressure. Water (50 ml) was added with stirring, and the pH value was adjusted to 2-3 with 10% dilute hydrochloric acid. White crystals slowly precipitated, which were filtered and dried to obtain 12 g of a white solid with a yield of 80%.

[0374] (2) Synthesis of 2-chloro-3-[(5-methyl-2-oxo-1,3,4-oxadiazol-3(2H)yl)methyl]-4-isopropylsulfonylbenzoate (1,3-dimethylpyrazol-5-yl)

[0375] To a reaction flask, 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) were added, followed by the slow addition of oxalyl chloride (7.6 g, 60 mmol). The mixture was heated under reflux for 4 hours. The solvent and excess oxalyl chloride were evaporated under reduced pressure, followed by the addition of dichloroethane (60 mL) and 1,3-dimethyl-5-hydroxypyrazole (2.3 g, 20.5 mmol). Triethylamine (3.2 g, 32 mmol) was then added dropwise. The mixture was stirred at room temperature for 1 hour, followed by the addition of water (50 mL). The aqueous phase was extracted twice with dichloroethane (30 mL x 2). The combined oily phases were evaporated, the solvent evaporated, and the residue was separated by column chromatography to yield 6.1 g of a light yellow solid, a 65% yield.

[0376] (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)

[0377] To a reaction flask were added 2-chloro-3-[(5-methyl-2-oxo-1,3,4-oxadiazol-3(2H)yl)methyl)]-4-isopropylsulfonylbenzoate (6.1 g, 13 mmol), dichloromethane (100 ml), triethylamine (1.9 g, 19 mmol), and acetone cyanohydrin (2 ml). The mixture was reacted at room temperature for 12 hours. Water (60 ml) was added to the reaction solution for extraction, and the mixture was stirred for half an hour. The pH value 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 light yellow solid with a yield of 96%.

[0378] Example 4 Synthesis of Compound 171

[0379] To a reaction flask were added 1-methyl-3-trifluoromethyl-4-pyrazolecarboxylic acid (4.5 g, 23 mmol) and dichloroethane (80 ml), and thionyl chloride (7.1 g, 60 mmol) was slowly added. The mixture was heated under reflux for 4 hours. The solvent and excess thionyl chloride were evaporated under reduced pressure, and dichloroethane (80 ml) and 3-{2-chloro-3-[(1-methyl-5-hydroxy-1H-pyrazol-4-yl)carbonyl]-6-ethylsulfonylbenzyl}-5-methyl-1,3,4-oxadiazol-2(3H)-one (7.2 g, 15.8 mmol) were added. Triethylamine (3 g, 30 mmol) was added dropwise, and 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*2). The oil phases were combined, washed with saturated brine (60 ml), dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was separated by column chromatography to obtain 10.1 g of solid (yield 70%).

[0380] Example 5 Determination of herbicidal activity

[0381] Broadleaf weeds (Abelmoschus flax, Solanum nigrum) or grass weeds (Digitaria sanguinea, Echinochloa crus-galli) were sown in plastic cups filled with nutrient soil. After sowing, the seeds were covered with soil, suppressed, and watered, and then cultured in a greenhouse according to conventional methods. After the weeds reached the 2-3 leaf stage, the stems and leaves were sprayed. The test compounds of the present application were dissolved in acetone, and then Tween 80 was added. 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 natural drying in the shade, the plants were placed in a greenhouse and managed according to conventional methods. The growth and development of the weeds were observed, and the control effect of the test agents on the weeds was regularly visually inspected. The control effect was expressed as 0-100%, with "0" representing no control effect and "100%" representing complete kill or severe inhibition.

[0382] The test results show that the compound of general formula I generally has a high control effect on broad-leaved weeds and grass weeds. Among some of the tested compounds, such as 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, when applied at a rate of 300 g a.i. / ha, the control effect was 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 had a good control effect on crabgrass when applied at a rate of 300 g a.i. / ha. ai / ha, the 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 had good control effects on velvetleaf and nightshade at an application rate of 300 g ai / ha, with control effects of more than 90%.

[0383] According to the above test method, compounds 1, 32, 49, 166, 194, 201, 204, 218, 224, and 228 were selected and tested for herbicidal activity together with control compounds A, B, and C. The activity data on velvetleaf, Solanum nigrum, crabgrass, and barnyard grass are shown in Table 5. Table 5 shows the post-emergence weed test results of the compounds provided in the Examples of the present application.

[0384] Table 5 Post-emergence weed test results of the compounds provided in the examples of this application

[0385] Wherein, the control compound A is:

[0386] The control compound B is:

[0387] The control compound C is:

[0388] As shown in 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 in the present application have good herbicidal activity against velvetleaf, Solanum nigrum, crabgrass, barnyard grass, etc. at different dosages.

[0389] Example 6 Determination of safety of corn and rice

[0390] Corn and rice seeds were sown in plastic cups filled with nutrient soil, covered with soil, pressed, and watered, and then cultured in a greenhouse according to conventional methods. After the crops reached the 2-3 leaf stage, the stems and leaves were sprayed. The test compounds of the present application were dissolved in acetone, and then Tween 80 was added. The solution was diluted with a certain amount of water to form a solution of a certain solubility and sprayed on the plants using a spray tower. The test was repeated 3 times. After natural drying in the shade, the plants were placed in a greenhouse and managed according to conventional methods. The growth and development of corn and rice were observed, and the safety of the test agents on corn and rice was visually inspected regularly. Safety grading standard: expressed as 0-100%, with "0" representing no damage to the crop and "100%" representing complete killing or severe inhibition of the crop. Some test results are shown in Table 6, which shows the corn and rice safety test results of the compounds provided in the examples of the present application.

[0391] Table 6 Corn and rice safety test results of the compounds provided in the examples of this application

[0392] The control compound A is:

[0393] The control compound B is:

[0394] The control compound C is:

[0395] As shown in Table 6, compared with the control compounds A, B and C, compounds 6, 58, 100, 201, 224, 228 and compound 233 provided in the present application had no obvious inhibitory effect on corn and rice at different doses.

[0396] Finally, it should be noted that the above embodiments are only used to illustrate the technical solutions of the present application, rather than to limit them. Although the present application has been described in detail with reference to the aforementioned embodiments, those skilled in the art should understand that they can still modify the technical solutions described in the aforementioned embodiments, or make equivalent replacements for some of the technical features therein. However, these modifications or replacements do not deviate the essence of the corresponding technical solutions from the spirit and scope of the technical solutions of the present application. Industrial Applicability

[0397] The applicant has substituted the sulfonyl group and Cl group on the benzene ring of a benzoyl compound with an oxadiazolone group represented by formula (a), resulting in an oxadiazolone compound that not only exhibits unexpectedly high herbicidal activity against a variety of weeds but is also relatively safe for crops such as corn and rice. Experimental results demonstrate that the compound provided by this application exhibits strong herbicidal activity, effectively controlling weeds such as barnyardgrass, crabgrass, and velvetleaf at low doses, achieving excellent weed control while remaining relatively safe for crops.

Claims

1. An oxadiazolone compound represented by formula (I) or its tautomer: In formula (I), R1 and R2 are independently selected from C1-C6 alkyl or C3-C6 cycloalkyl groups which are unsubstituted or substituted by 1 to 3 groups independently selected from the following groups: halogen, nitro, C1-C6 alkyl, halogenated C1-C6 alkyl, C1-C6 alkoxy or halogenated C1-C6 alkoxy; Q is selected from the structure shown by Q1, Q2 or Q3: in, A1, A2, A3, A4 and A5 are independently selected from O or S; R3 and R 10 independently selected from hydrogen, C1-C6 alkyl, C3-C6 cycloalkyl, C1-C6 alkoxy, phenyl or benzyl, which is unsubstituted or substituted by 1 to 3 groups independently selected from the following groups: halogen, nitro, C1-C6 alkyl, halogenated C1-C6 alkyl, C1-C6 alkoxy, halogenated C1-C6 alkoxy, phenyl or halogenated phenyl; n is an integer from 1 to 6; R4 is selected from hydrogen, halogen, C1-C6 alkyl, C3-C6 cycloalkyl or C1-C6 alkoxy which is unsubstituted or substituted by 1 to 3 groups independently selected from the following groups: halogen, nitro, C1-C6 alkyl, halogenated C1-C6 alkyl, C1-C6 alkoxy or halogenated C1-C6 alkoxy; R5 is selected from hydrogen, C1-C6 alkyl or C3-C6 cycloalkyl which is unsubstituted or substituted by 1 to 3 groups independently selected from the following groups: halogen, nitro, C1-C6 alkyl, halogenated C1-C6 alkyl, C1-C6 alkoxy or halogenated C1-C6 alkoxy; R6 is selected from hydrogen, the structure represented by formula (1), C1-C6 alkyl, C3-C6 cycloalkyl, C3-C8 heterocycloalkyl which is unsubstituted or substituted by 1-3 groups independently selected from the following groups: halogen, nitro, C1-C6 alkyl, halogenated C1-C6 alkyl, C1-C6 alkoxy or halogenated C1-C6 alkoxy; In formula (1), A6 is selected from N or CR9, and R9 is selected from hydrogen, C1-C6 alkyl, C3-C6 cycloalkyl or C1-C6 alkoxy which is unsubstituted or substituted by 1 to 3 groups independently selected from the following groups: halogen, nitro, C1-C6 alkyl, halogenated C1-C6 alkyl, C1-C6 alkoxy or halogenated C1-C6 alkoxy; R7 and R8 are independently selected from hydrogen, C1-C6 alkyl, C3-C6 cycloalkyl or C1-C6 alkoxy which is unsubstituted or substituted by 1-3 groups independently selected from the following groups: halogen, nitro, C1-C6 alkyl, halogenated C1-C6 alkyl, C1-C6 alkoxy or halogenated C1-C6 alkoxy; R7 and R8 are not H at the same time; Alternatively, R7, R8 and A6 where they are located form a C3-C8 ring that is unsubstituted or substituted by 1 to 3 groups independently selected from the following groups and contains 0 to 3 heteroatoms: halogen, nitro, C1-C6 alkyl, C3-C6 cycloalkyl, halogenated C1-C6 alkyl, C1-C6 alkoxy or halogenated C1-C6 alkoxy; the heteroatoms are selected from oxygen, sulfur or nitrogen.

2. The oxadiazolone compound or its tautomer according to claim 1, characterized in that: Q is selected from the structure shown in Q1-1: R3 is selected from H, C1-C4 alkyl or C1-C4 haloalkyl; R1 and R2 are independently selected from C1-C4 alkyl, C3-C6 cycloalkyl or C1-C4 haloalkyl; or, Q is selected from the structure shown in Q3-1: R 10 Selected from H, C1-C4 alkyl, C1-C4 haloalkyl, phenyl, halophenyl, C1-C4 alkyl substituted with phenyl or C1-C4 alkyl substituted with halophenyl; R1 and R2 are independently selected from C1-C4 alkyl, C3-C6 cycloalkyl or C1-C4 haloalkyl; or, Q is selected from the structure shown in Q2-1: X1 is selected from C or N, X2 is selected from C, N, O or S, and X1 and X2 are not C at the same time; R 11 Selected from H, halogen, C1-C4 alkyl, C3-C6 cycloalkyl or C1-C4 haloalkyl; m is an integer from 1 to 3; R4 is selected from hydrogen, halogen, C1-C4 alkyl, halogenated C1-C4 alkyl, C3-C6 cycloalkyl, halogenated C3-C6 cycloalkyl, C1-C4 alkoxy, halogenated C1-C4 alkoxy; R5 is selected from hydrogen, C1-C4 alkyl or halogenated C1-C4 alkyl; R1 and R2 are independently selected from C1-C4 alkyl, C3-C6 cycloalkyl or C1-C4 haloalkyl.

3. The oxadiazolone compound or its tautomer according to claim 2, characterized in that: R1 and R2 are independently selected from -CH3, -CH2CH3, -CH2CH2CH3, -CH(CH3)2, -C(CH3)3, -CH2CH2CH2CH3, -CF3, -CH2CF3, -CH2CH2CF3, -CH(CF3)2, -C(CF3)3, -CHCH3CF3, -C(CH3)2CF3 or CCH2(CF3)2.

4. The oxadiazolone compound or its tautomer according to claim 3, characterized in that: R 10 Selected from H, -CH3, -CH2CH3, -CH2CH2CH3, -CH(CH3)2, -C(CH3)3, -CH2CH2CH2CH3, phenyl, chlorophenyl, dichlorophenyl, C6H5CH2-, C6H4ClCH2- or C6H3Cl2CH2-; R 11 Selected from H, CH3, CF3, -CH2CH 3、 Cyclopropyl or Cl.

5. The oxadiazolone compound or its tautomer according to claim 1, characterized in that: R6 is selected from hydrogen or the structure shown in formula (1): In formula (1), A6 is selected from N, R7 and R8 are independently selected from hydrogen, C1-C4 alkyl, halogenated C1-C4 alkyl, C3-C6 cycloalkyl, C1-C4 alkoxy or halogenated C1-C4 alkoxy; R7 and R8 are not H at the same time; Alternatively, A6 is selected from N or C, and R7, R8 and A6 form a C3-C8 ring which is unsubstituted or substituted by 1-3 groups independently selected from the following groups and contains 1-3 heteroatoms: halogen, nitro, C1-C4 alkyl, halogenated C1-C4 alkyl, C1-C4 alkoxy or halogenated C1-C4 alkoxy; the heteroatom is selected from oxygen, sulfur or nitrogen.

6. The oxadiazolone compound or its tautomer according to claim 5, characterized in that: R6 is selected from the following structures: Among them, R 1 , R 3 , R 4 , R 6 Independently selected from hydrogen, halogen, C1-C4 alkyl, halogenated C1-C4 alkyl or C3-C6 cycloalkyl; R 2 , R 5 , R 7 Independently selected from hydrogen, C1-C4 alkyl, halogenated C1-C4 alkyl or C3-C6 cycloalkyl.

7. The oxadiazolone compound or its tautomer according to claim 1, characterized in that: Selected from the following compounds: Compound 1: Q is selected from the structure shown in Q1-1, R1=CH3, R2=CH3, R3=H; Compound 2: Q is selected from the structure shown in Q1-1, R1=CH3, R2=CH2CH3, R3=H; Compound 3: Q is selected from the structure shown in Q1-1, R1=CH3, R2=CH2CH2CH3, R3=H; Compound 4: Q is selected from the structure shown in Q1-1, R1=CH3, R2=C(CH3)3, R3=H; Compound 5: Q is selected from the structure shown in Q1-1, R1=CH3, R2=CF3, R3=H; Compound 6: Q is selected from the structure shown in Q1-1, R1=CH2CH3, R2=CH3, R3=H; Compound 7: Q is selected from the structure shown in Q1-1, R1=CH2CH3, R2=CH2CH3, R3=H; Compound 8: Q is selected from the structure shown in Q1-1, R1=CH2CH3, R2=CH2CH2CH3, R3=H; Compound 9: Q is selected from the structure shown in Q1-1, R1=CH2CH3, R2=C(CH3)3, R3=H; Compound 10: Q is selected from the structure shown in Q1-1, R1=CH2CH3, R2=CF3, R3=H; Compound 11: Q is selected from the structure shown in Q1-1, R1=CH2CH2CH3, R2=CH3, R3=H; Compound 12: Q is selected from the structure shown in Q1-1, R1=CH2CH2CH3, R2=CH2CH3, R3=H; Compound 13: Q is selected from the structure shown in Q1-1, R1=CH2CH2CH3, R2=CH2CH2CH3, R3=H; Compound 14: Q is selected from the structure shown in Q1-1, R1=CH2CH2CH3, R2=C(CH3)3, R3=H; Compound 15: Q is selected from the structure shown in Q1-1, R1=CH2CH2CH3, R2=CF3, R3=H; Compound 16: Q is selected from the structure shown in Q1-1, R1=CH(CH3)2, R2=CH3, R3=H; Compound 17: Q is selected from the structure shown in Q1-1, R1=CH(CH3)2, R2=CH2CH3, R3=H; Compound 18: Q is selected from the structure shown in Q1-1, R1=CH(CH3)2, R2=CH2CH2CH3, R3=H; Compound 19: Q is selected from the structure shown in Q1-1, R1=CH(CH3)2, R2=C(CH3)3, R3=H; Compound 20: Q is selected from the structure shown in Q1-1, R1=CH(CH3)2, R2=CF3, R3=H; Compound 21: Q is selected from the structure shown in Q1-1, R1=CH2CH2CH2CH3, R2=CH3, R3=H; Compound 22: Q is selected from the structure shown in Q1-1, R1=CH2CH2CH2CH3, R2=CH2CH3, R3=H; Compound 23: Q is selected from the structure shown in Q1-1, R1=CH2CH2CH2CH3, R2=CH2CH2CH3, R3=H; Compound 24: Q is selected from the structure shown in Q1-1, R1=CH2CH2CH2CH3, R2=C(CH3)3, R3=H; Compound 25: Q is selected from the structure shown in Q1-1, R1=CH2CH2CH2CH3, R2=CF3, R3=H; Compound 26: Q is selected from the structure shown in Q1-1, R1=C(CH3)3, R2=CH3, R3=H; Compound 27: Q is selected from the structure shown in Q1-1, R1=C(CH3)3, R2=CH2CH3, R3=H; Compound 28: Q is selected from the structure shown in Q1-1, R1=C(CH3)3, R2=CH2CH2CH3, R3=H; Compound 29: Q is selected from the structure shown in Q1-1, R1=C(CH3)3, R2=C(CH3)3, R3=H; Compound 30: Q is selected from the structure shown in Q1-1, R1=C(CH3)3, R2=CF3, R3=H; Compound 31: Q is selected from the structure shown in Q3, R1=CH3, R2=CH3, A4=O, A5=O, R 10 =CH3; Compound 32: Q is selected from the structure shown in Q3, R1=CH3, R2=CH3, A4=O, A5=O, R 10 =CH2CH3; Compound 33: Q is selected from the structure shown in Q3, R1=CH3, R2=CH3, A4=O, A5=O, R 10 =CH2CH2CH3; Compound 34: Q is selected from the structure shown in Q3, R1=CH3, R2=CH3, A4=O, A5=O, R 10 =CH(CH3)2; Compound 35: Q is selected from the structure shown in Q3, R1=CH3, R2=CH3, A4=O, A5=O, R 10 =CH2CH2CH2CH3; Compound 36: Q is selected from the structure shown in Q3, R1=CH3, R2=CH3, A4=O, A5=O, R 10 =C(CH3)3; Compound 37: Q is selected from the structure shown in Q3, R1=CH3, R2=CH3, A4=O, A5=O, Compound 38: Q is selected from the structure shown in Q3, R1=CH3, R2=CH3, A4=O, A5=O, Compound 39: Q is selected from the structure shown in Q3, R1=CH3, R2=CH3, A4=O, A5=O, Compound 40: Q is selected from the structure shown in Q3, R1=CH3, R2=CH3, A4=O, A5=O, Compound 41: Q is selected from the structure shown in Q3, R1=CH3, R2=CH3, A4=O, A5=O, Compound 42: Q is selected from the structure shown in Q3, R1=CH3, R2=CH3, A4=O, A5=O, Compound 43: Q is selected from the structure shown in Q3, R1=CH3, R2=CH3, A4=O, A5=O, Compound 44: Q is selected from the structure shown in Q3, R1=CH3, R2=CH3, A4=O, A5=S, R 10 =CH3; Compound 45: Q is selected from the structure shown in Q3, R1=CH3, R2=CH3, A4=O, A5=S, R 10 =CH2CH3; Compound 46: Q is selected from the structure shown in Q3, R1=CH3, R2=CH3, A4=O, A5=S, R 10 =CH2CH2CH3; Compound 47: Q is selected from the structure shown in Q3, R1=CH3, R2=CH3, A4=O, A5=S, R 10 =CH(CH3)2; Compound 48: Q is selected from the structure shown in Q3, R1=CH3, R2=CH3, A4=O, A5=S, R 10 =CH2CH2CH2CH3; Compound 49: Q is selected from the structure shown in Q3, R1=CH3, R2=CH3, A4=O, A5=S, R 10 =C(CH3)3; Compound 50: Q is selected from the structure shown in Q3, R1=CH3, R2=CH3, A4=O, A5=S, Compound 51: Q is selected from the structure shown in Q3, R1=CH3, R2=CH3, A4=O, A5=S, Compound 52: Q is selected from the structure shown in Q3, R1=CH3, R2=CH3, A4=O, A5=S, Compound 53: Q is selected from the structure shown in Q3, R1=CH3, R2=CH3, A4=O, A5=S, Compound 54: Q is selected from the structure shown in Q3, R1=CH3, R2=CH3, A4=O, A5=S, Compound 55: Q is selected from the structure shown in Q3, R1=CH3, R2=CH3, A4=O, A5=S, Compound 56: Q is selected from the structure shown in Q2, A3=O, R1=CH3, R2=CH3, R4=H, R5=CH3, R6=H; Compound 57: Q is selected from the structure shown in Q2, A3=O, R1=CH3, R2=CH3, R4=H, R5=CH2CH3, R6=H; Compound 58: Q is selected from the structure shown in Q2, A3=O, R1=CH3, R2=CH3, R4=CH3, R5=CH3, R6=H; Compound 59: Q is selected from the structure shown in Q2, A3=O, R1=CH3, R2=CH3, R4=CH3, R5=CH2CH3, R6=H; Compound 60: Q is selected from the structure shown in Q2, A3=O, R1=CH3, R2=CH3, R4=CH2CH3, R5=CH3, R6=H; Compound 61: Q is selected from the structure shown in Q2, A3=O, R1=CH3, R2=CH3, R4=CH2CH3, R5=CH2CH3, R6=H; Compound 62: Q is selected from the structure shown in Q2, A3=O, R1=CH3, R2=CH3, R4=CH2CH2CH3, R5=CH3, R6=H; Compound 63: Q is selected from the structure shown in Q2, A3=O, R1=CH3, R2=CH3, R4=CH2CH2CH3, R5=CH2CH3, R6=H; Compound 64: Q is selected from the structure shown in Q2, A3=O, R1=CH3, R2=CH3, R4=CH(CH3)2, R5=CH3, R6=H; Compound 65: Q is selected from the structure shown in Q2, A3=O, R1=CH3, R2=CH3, R4=CH(CH3)2, R5=CH2CH3, R6=H; Compound 66: Q is selected from the structure shown in Q2, A3=O, R1=CH3, R2=CH3, R4=CF3, R5=CH3, R6=H; Compound 67: Q is selected from the structure shown in Q2, A3=O, R1=CH3, R2=CH3, R4=CF3, R5=CH2CH3, R6=H; Compound 68: Q is selected from the structure shown in Q2, A3=O, R1=CH3, R2=CH3, R5=CH3,R6=H; Compound 69: Q is selected from the structure shown in Q2, A3=O, R1=CH3, R2=CH3, R5=CH2CH3, R6=H; Compound 70: Q is selected from the structure shown in Q2, A3=O, R1=CH2CH3, R2=CH3, R4=H, R5=CH3, R6=H; Compound 71: Q is selected from the structure shown in Q2, A3=O, R1=CH2CH3, R2=CH3, R4=H, R5=CH2CH3, R6=H; Compound 72: Q is selected from the structure shown in Q2, A3=O, R1=CH2CH3, R2=CH3, R4=CH3, R5=CH3, R6=H; Compound 73: Q is selected from the structure shown in Q2, A3=O, R1=CH2CH3, R2=CH3, R4=CH3, R5=CH2CH3, R6=H; Compound 74: Q is selected from the structure shown in Q2, A3=O, R1=CH2CH3, R2=CH3, R4=CH2CH3, R5=CH3, R6=H; Compound 75: Q is selected from the structure shown in Q2, A3=O, R1=CH2CH3, R2=CH3, R4=CH2CH3, R5=CH2CH3, R6=H; Compound 76: Q is selected from the structure shown in Q2, A3=O, R1=CH2CH3, R2=CH3, R4=CH2CH2CH3, R5=CH3, R6=H; Compound 77: Q is selected from the structure shown in Q2, A3=O, R1=CH2CH3, R2=CH3, R4=CH2CH2CH3, R5=CH2CH3, R6=H; Compound 78: Q is selected from the structure shown in Q2, A3=O, R1=CH2CH3, R2=CH3, R4=CH(CH3)2, R5=CH3, R6=H; Compound 79: Q is selected from the structure shown in Q2, A3=O, R1=CH2CH3, R2=CH3, R4=CH(CH3)2, R5=CH2CH3, R6=H; Compound 80: Q is selected from the structure shown in Q2, A3=O, R1=CH2CH3, R2=CH3, R4=CF3, R5=CH3, R6=H; Compound 81: Q is selected from the structure shown in Q2, A3=O, R1=CH2CH3, R2=CH3, R4=CF3, R5=CH2CH3, R6=H; Compound 82: Q is selected from the structure shown in Q2, A3=O, R1=CH2CH3, R2=CH3, R5=CH3,R6=H; Compound 83: Q is selected from the structure shown in Q2, A3=O, R1=CH2CH3, R2=CH3, R5=CH2CH3, R6=H; Compound 84: Q is selected from the structure shown in Q2, A3=O, R1=CH2CH2CH3, R2=CH3, R4=H, R5=CH3, R6=H; Compound 85: Q is selected from the structure shown in Q2, A3=O, R1=CH2CH2CH3, R2=CH3, R4=H, R5=CH2CH3, R6=H; Compound 86: Q is selected from the structure shown in Q2, A3=O, R1=CH2CH2CH3, R2=CH3, R4=CH3, R5=CH3, R6=H; Compound 87: Q is selected from the structure shown in Q2, A3=O, R1=CH2CH2CH3, R2=CH3, R4=CH3, R5=CH2CH3, R6=H; Compound 88: Q is selected from the structure shown in Q2, A3=O, R1=CH2CH2CH3, R2=CH3, R4=CH2CH3, R5=CH3, R6=H; Compound 89: Q is selected from the structure shown in Q2, A3=O, R1=CH2CH2CH3, R2=CH3, R4=CH2CH3, R5=CH2CH3, R6=H; Compound 90: Q is selected from the structure shown in Q2, A3=O, R1=CH2CH2CH3, R2=CH3, R4=CH2CH2CH3, R5=CH3, R6=H; Compound 91: Q is selected from the structure shown in Q2, A3=O, R1=CH2CH2CH3, R2=CH3, R4=CH2CH2CH3, R5=CH2CH3, R6=H; Compound 92: Q is selected from the structure shown in Q2, A3=O, R1=CH2CH2CH3, R2=CH3, R4=CH(CH3)2, R5=CH3, R6=H; Compound 93: Q is selected from the structure shown in Q2, A3=O, R1=CH2CH2CH3, R2=CH3, R4=CH(CH3)2, R5=CH2CH3, R6=H; Compound 94: Q is selected from the structure shown in Q2, A3=O, R1=CH2CH2CH3, R2=CH3, R4=CF3, R5=CH3, R6=H; Compound 95: Q is selected from the structure shown in Q2, A3=O, R1=CH2CH2CH3, R2=CH3, R4=CF3, R5=CH2CH3, R6=H; Compound 96: Q is selected from the structure shown in Q2, A3=O, R1=CH2CH2CH3, R2=CH3, R5=CH3,R6=H; Compound 97: Q is selected from the structure shown in Q2, A3=O, R1=CH2CH2CH3, R2=CH3, R5=CH2CH3, R6=H; Compound 98: Q is selected from the structure shown in Q2, A3=O, R1=CH(CH3)2, R2=CH3, R4=H, R5=CH3, R6=H; Compound 99: Q is selected from the structure shown in Q2, A3=O, R1=CH(CH3)2, R2=CH3, R4=H, R5=CH2CH3, R6=H; Compound 100: Q is selected from the structure shown in Q2, A3=O, R1=CH(CH3)2, R2=CH3, R4=CH3, R5=CH3, R6=H; Compound 101: Q is selected from the structure shown in Q2, A3=O, R1=CH(CH3)2, R2=CH3, R4=CH3, R5=CH2CH3, R6=H; Compound 102: Q is selected from the structure shown in Q2, A3=O, R1=CH(CH3)2, R2=CH3, R4=CH2CH3, R5=CH3, R6=H; Compound 103: Q is selected from the structure shown in Q2, A3=O, R1=CH(CH3)2, R2=CH3, R4=CH2CH3, R5=CH2CH3, R6=H; Compound 104: Q is selected from the structure shown in Q2, A3=O, R1=CH(CH3)2, R2=CH3, R4=CH2CH2CH3, R5=CH3, R6=H; Compound 105: Q is selected from the structure shown in Q2, A3=O, R1=CH(CH3)2, R2=CH3, R4=CH2CH2CH3, R5=CH2CH3, R6=H; Compound 106: Q is selected from the structure shown in 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 shown in 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 shown in Q2, A3=O, R1=CH(CH3)2, R2=CH3, R4=CF3, R5=CH3, R6=H; Compound 109: Q is selected from the structure shown in Q2, A3=O, R1=CH(CH3)2, R2=CH3, R4=CF3, R5=CH2CH3, R6=H; Compound 110: Q is selected from the structure shown in Q2, A3=O, R1=CH(CH3)2, R2=CH3, R5=CH3,R6=H; Compound 111: Q is selected from the structure shown in Q2, A3=O, R1=CH(CH3)2, R2=CH3, R5=CH2CH3, R6=H; Compound 112: Q is selected from the structure shown in Q2, A3=O, R1=CH2CH2CH2CH3, R2=CH3, R4=H, R5=CH3, R6=H; Compound 113: Q is selected from the structure shown in Q2, A3=O, R1=CH2CH2CH2CH3, R2=CH3, R4=H, R5=CH2CH3, R6=H; Compound 114: Q is selected from the structure shown in Q2, A3=O, R1=CH2CH2CH2CH3, R2=CH3, R4=CH3, R5=CH3, R6=H; Compound 115: Q is selected from the structure shown in Q2, A3=O, R1=CH2CH2CH2CH3, R2=CH3, R4=CH3, R5=CH2CH3, R6=H; Compound 116: Q is selected from the structure shown in Q2, A3=O, R1=CH2CH2CH2CH3, R2=CH3, R4=CH2CH3, R5=CH3, R6=H; Compound 117: Q is selected from the structure shown in Q2, A3=O, R1=CH2CH2CH2CH3, R2=CH3, R4=CH2CH3, R5=CH2CH3, R6=H; Compound 118: Q is selected from the structure shown in Q2, A3=O, R1=CH2CH2CH2CH3, R2=CH3, R4=CH2CH2CH3, R5=CH3, R6=H; Compound 119: Q is selected from the structure shown in Q2, A3=O, R1=CH2CH2CH2CH3, R2=CH3, R4=CH2CH2CH3, R5=CH2CH3, R6=H; Compound 120: Q is selected from the structure shown in Q2, A3=O, R1=CH2CH2CH2CH3, R2=CH3, R4=CH(CH3)2, R5=CH3, R6=H; Compound 121: Q is selected from the structure shown in Q2, A3=O, R1=CH2CH2CH2CH3, R2=CH3, R4=CH(CH3)2, R5=CH2CH3, R6=H; Compound 122: Q is selected from the structure shown in Q2, A3=O, R1=CH2CH2CH2CH3, R2=CH3, R4=CF3, R5=CH3, R6=H; Compound 123: Q is selected from the structure shown in Q2, A3=O, R1=CH2CH2CH2CH3, R2=CH3, R4=CF3, R5=CH2CH3, R6=H; Compound 124: Q is selected from the structure shown in Q2, A3=O, R1=CH2CH2CH2CH3, R2=CH3, R5=CH3,R6=H; Compound 125: Q is selected from the structure shown in Q2, A3=O, R1=CH2CH2CH2CH3, R2=CH3, R5=CH2CH3, R6=H; Compound 126: Q is selected from the structure shown in Q2, A3=O, R1=C(CH3)3, R2=CH3, R4=H, R5=CH3, R6=H; Compound 127: Q is selected from the structure shown in Q2, A3=O, R1=C(CH3)3, R2=CH3, R4=H, R5=CH2CH3, R6=H; Compound 128: Q is selected from the structure shown in Q2, A3=O, R1=C(CH3)3, R2=CH3, R4=CH3, R5=CH3, R6=H; Compound 129: Q is selected from the structure shown in Q2, A3=O, R1=C(CH3)3, R2=CH3, R4=CH3, R5=CH2CH3, R6=H; Compound 130: Q is selected from the structure shown in Q2, A3=O, R1=C(CH3)3, R2=CH3, R4=CH2CH3, R5=CH3, R6=H; Compound 131: Q is selected from the structure shown in Q2, A3=O, R1=C(CH3)3, R2=CH3, R4=CH2CH3, R5=CH2CH3, R6=H; Compound 132: Q is selected from the structure shown in Q2, A3=O, R1=C(CH3)3, R2=CH3, R4=CH2CH2CH3, R5=CH3, R6=H; Compound 133: Q is selected from the structure shown in Q2, A3=O, R1=C(CH3)3, R2=CH3, R4=CH2CH2CH3, R5=CH2CH3, R6=H; Compound 134: Q is selected from the structure shown in 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 shown in 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 shown in Q2, A3=O, R1=C(CH3)3, R2=CH3, R4=CF3, R5=CH3, R6=H; Compound 137: Q is selected from the structure shown in Q2, A3=O, R1=C(CH3)3, R2=CH3, R4=CF3, R5=CH2CH3, R6=H; Compound 138: Q is selected from the structure shown in Q2, A3=O, R1=C(CH3)3, R2=CH3, R5=CH3,R6=H; Compound 139: Q is selected from the structure shown in Q2, A3=O, R1=C(CH3)3, R2=CH3, R5=CH2CH3, R6=H; Compound 140: Q is selected from the structure shown in Q2, A3=S, R1=CH3, R2=CH3, R4=CH3, R5=CH3, R6=(CH3CH2)2NCO; Compound 141: Q is selected from the structure shown in Q2, A3=O, R1=CH3, R2=CH3, R4=CH3, R5=CH3, R6=(CH3CH2CH2)2NCO; Compound 142: Q is selected from the structure shown in Q2, A3=O, R1=CH2CH3, R2=CH3, R4=CH3, R5=CH3, R6=(CH3CH2CH2)2NCO; Compound 143: Q is selected from the structure shown in Q2, A3=O, R1=CH(CH3)2, R2=CH3, R4=CH3, R5=CH3, R6=(CH3CH2CH2)2NCO; Compound 144: Q is selected from the structure shown in Q2, A3=O, R1=CH3, R2=CH3, R5=CH3, R6=(CH3CH2CH2)2NCO; Compound 145: Q is selected from the structure shown in Q2, A3=S, R1=CH3, R2=CH3, R4=CH3, R5=CH3, R6=(CH3OCH2CH2)2NCO; Compound 146: Q is selected from the structure shown in Q2, A3=S, R1=CH3, R2=CH3, R4=CH3, R5=CH3, Compound 147: Q is selected from the structure shown in Q2, A3=S, R1=CH3, R2=CH3, R4=CH3, R5=CH3, Compound 148: Q is selected from the structure shown in Q2, A3=S, R1=CH3, R2=CH3, R4=CH3, R5=CH3, Compound 149: Q is selected from the structure shown in Q2, A3=O, R1=CH3, R2=CH3, R4=CH3, R5=CH3, Compound 150: Q is selected from the structure shown in Q2, A3=O, R1=CH2CH3, R2=CH3, R4=CH3, R5=CH3, Compound 151: Q is selected from the structure shown in Q2, A3=O, R1=CH(CH3)2, R2=CH3, R4=CH3, R5=CH3, Compound 152: Q is selected from the structure shown in Q2, A3=O, R1=CH3, R2=CH3, R5=CH3, Compound 153: Q is selected from the structure shown in Q2, A3=O, R1=CH2CH3, R2=CH3, R5=CH3, Compound 154: Q is selected from the structure shown in Q2, A3=O, R1=CH3, R2=CH3, R4=CH3, R5=CH3, Compound 155: Q is selected from the structure shown in Q2, A3=O, R1=CH2CH3, R2=CH3, R4=CH3, R5=CH3, Compound 156: Q is selected from the structure shown in Q2, A3=O, R1=CH2CH2CH3, R2=CH3, R4=CH3, R5=CH3, Compound 157: Q is selected from the structure shown in Q2, A3=O, R1=CH(CH3)2, R2=CH3, R4=CH3, R5=CH3, Compound 158: Q is selected from the structure shown in Q2, A3=O, R1=CH3, R2=CH3, R4=H, R5=CH3, Compound 159: Q is selected from the structure shown in Q2, A3=O, R1=CH2CH3, R2=CH3, R4=H, R5=CH3, Compound 160: Q is selected from the structure shown in Q2, A3=O, R1=CH2CH2CH3, R2=CH3, R4=H, R5=CH3, Compound 161: Q is selected from the structure shown in Q2, A3=O, R1=CH(CH3)2, R2=CH3, R4=H, R5=CH3, Compound 162: Q is selected from the structure shown in Q2, A3=O, R1=CH3, R2=CH3, R5=CH3, Compound 163: Q is selected from the structure shown in Q2, A3=O, R1=CH2CH3, R2=CH3, R5=CH3, Compound 164: Q is selected from the structure shown in Q2, A3=O, R1=CH2CH2CH3, R2=CH3, R5=CH3, Compound 165: Q is selected from the structure shown in Q2, A3=O, R1=CH(CH3)2, R2=CH3, R5=CH3, Compound 166: Q is selected from the structure shown in Q2, A3=O, R1=CH3, R2=CH3, R4=CH3, R5=CH3, Compound 167: Q is selected from the structure shown in Q2, A3=O, R1=CH2CH3, R2=CH3, R4=CH3, R5=CH3, Compound 168: Q is selected from the structure shown in Q2, A3=O, R1=CH2CH2CH3, R2=CH3, R4=CH3, R5=CH3, Compound 169: Q is selected from the structure shown in Q2, A3=O, R1=CH(CH3)2, R2=CH3, R4=CH3, R5=CH3, Compound 170: Q is selected from the structure shown in Q2, A3=O, R1=CH3, R2=CH3, R4=H, R5=CH3, Compound 171: Q is selected from the structure shown in Q2, A3=O, R1=CH2CH3, R2=CH3, R4=H, R5=CH3, Compound 172: Q is selected from the structure shown in Q2, A3=O, R1=CH2CH2CH3, R2=CH3, R4=H, R5=CH3, Compound 173: Q is selected from the structure shown in Q2, A3=O, R1=CH(CH3)2, R2=CH3, R4=H, R5=CH3, Compound 174: Q is selected from the structure shown in Q2, A3=O, R1=CH3, R2=CH3, R5=CH3, Compound 175: Q is selected from the structure shown in Q2, A3=O, R1=CH2CH3, R2=CH3, R5=CH3, Compound 176: Q is selected from the structure shown in Q2, A3=O, R1=CH2CH2CH3, R2=CH3, R5=CH3, Compound 177: Q is selected from the structure shown in Q2, A3=O, R1=CH(CH3)2, R2=CH3, R5=CH3, Compound 178: Q is selected from the structure shown in Q2, A3=O, R1=CH3, R2=CH3, R4=CH3, R5=CH3, Compound 179: Q is selected from the structure shown in Q2, A3=O, R1=CH2CH2CH3, R2=CH3, R4=CH3, R5=CH3, Compound 180: Q is selected from the structure shown in Q2, A3=O, R1=CH3, R2=CH3, R4=H, R5=CH3, Compound 181: Q is selected from the structure shown in Q2, A3=O, R1=CH2CH2CH3, R2=CH3, R4=H, R5=CH3, Compound 182: Q is selected from the structure shown in Q2, A3=O, R1=CH3, R2=CH3, R5=CH3, Compound 183: Q is selected from the structure shown in Q2, A3=O, R1=CH2CH2CH3, R2=CH3, R5=CH3, Compound 184: Q is selected from the structure shown in Q2, A3=O, R1=CH2CH3, R2=CH3, R4=CH3, R5=CH3, Compound 185: Q is selected from the structure shown in Q2, A3=O, R1=CH(CH3)2, R2=CH3, R4=CH3, R5=CH3, Compound 186: Q is selected from the structure shown in Q2, A3=O, R1=CH2CH3, R2=CH3, R4=H, R5=CH3, Compound 187: Q is selected from the structure shown in Q2, A3=O, R1=CH(CH3)2, R2=CH3, R4=H, R5=CH3, Compound 188: Q is selected from the structure shown in Q2, A3=O, R1=CH2CH3, R2=CH3, R5=CH3, Compound 189: Q is selected from the structure shown in Q2, A3=O, R1=CH(CH3)2, R2=CH3, R5=CH3, Compound 190: Q is selected from the structure shown in Q2, A3=O, R1=CH2CH3, R2=CH3, R4=CH3, R5=CH2CH3, Compound 191: Q is selected from the structure shown in Q2, A3=O, R1=CH3, R2=CH3, R4=H, R5=CH2CH3, Compound 192: Q is selected from the structure shown in Q2, A3=O, R1=CH2CH2CH3, R2=CH3, R5=CH2CH3, Compound 193: Q is selected from the structure shown in Q2, A3=O, R1=CH(CH3)2, R2=CH3, R5=CH2CH3, Compound 194: Q is selected from the structure shown in Q2, A3=O, R1=CH3, R2=CH3, R4=CH3, R5=CH3, Compound 195: Q is selected from the structure shown in Q2, A3=O, R1=CH2CH3, R2=CH3, R4=CH3, R5=CH3, Compound 196: Q is selected from the structure shown in Q2, A3=O, R1=CH2CH2CH3, R2=CH3, R4=CH3, R5=CH3, Compound 197: Q is selected from the structure shown in Q2, A3=O, R1=CH(CH3)2, R2=CH3, R4=CH3, R5=CH3, Compound 198: Q is selected from the structure shown in Q2, A3=O, R1=CH3, R2=CH3, R4=H, R5=CH3, Compound 199: Q is selected from the structure shown in Q2, A3=O, R1=CH2CH3, R2=CH3, R4=H, R5=CH3, Compound 200: Q is selected from the structure shown in Q2, A3=O, R1=CH(CH3)2, R2=CH3, R4=H, R5=CH3, Compound 201: Q is selected from the structure shown in Q2, A3=O, R1=CH3, R2=CH3, R5=CH3, Compound 202: Q is selected from the structure shown in Q2, A3=O, R1=CH2CH3, R2=CH3, R5=CH3, Compound 203: Q is selected from the structure shown in Q2, A3=O, R1=CH(CH3)2, R2=CH3, R5=CH3, Compound 204: Q is selected from the structure shown in Q2, A3=O, R1=CH3, R2=CH3, R4=CH3, R5=CH3, Compound 205: Q is selected from the structure shown in Q2, A3=O, R1=CH2CH3, R2=CH3, R4=CH3, R5=CH3, Compound 206: Q is selected from the structure shown in Q2, A3=O, R1=CH(CH3)2, R2=CH3, R4=CH3, R5=CH3, Compound 207: Q is selected from the structure shown in Q2, A3=O, R1=CH3, R2=CH3, R4=H, R5=CH3, Compound 208: Q is selected from the structure shown in Q2, A3=O, R1=CH2CH3, R2=CH3, R4=H, R5=CH3, Compound 209: Q is selected from the structure shown in Q2, A3=O, R1=CH2CH2CH3, R2=CH3, R4=H, R5=CH3, Compound 210: Q is selected from the structure shown in Q2, A3=O, R1=CH(CH3)2, R2=CH3, R4=H, R5=CH3, Compound 211: Q is selected from the structure shown in Q2, A3=O, R1=CH2CH3, R2=CH3, R5=CH3, Compound 212: Q is selected from the structure shown in Q2, A3=O, R1=CH(CH3)2, R2=CH3, R5=CH3, Compound 213: Q is selected from the structure shown in Q2, A3=O, R1=CH3, R2=CH3, R4=CH3, R5=CH3, Compound 214: Q is selected from the structure shown in Q2, A3=O, R1=CH2CH3, R2=CH3, R4=CH3, R5=CH3, Compound 215: Q is selected from the structure shown in Q2, A3=O, R1=CH(CH3)2, R2=CH3, R4=CH3, R5=CH3, Compound 216: Q is selected from the structure shown in Q2, A3=O, R1=CH3, R2=CH3, R5=CH3, Compound 217: Q is selected from the structure shown in Q2, A3=O, R1=CH(CH3)2, R2=CH3, R5=CH3, Compound 218: Q is selected from the structure shown in Q2, A3=O, R1=CH3, R2=CH3, R4=CH3, R5=CH3, Compound 219: Q is selected from the structure shown in Q2, A3=O, R1=CH2CH3, R2=CH3, R4=CH3, R5=CH3, Compound 220: Q is selected from the structure shown in Q2, A3=O, R1=CH(CH3)2, R2=CH3, R4=CH3, R5=CH3, Compound 221: Q is selected from the structure shown in Q2, A3=O, R1=CH3, R2=CH3, R5=CH3, Compound 222: Q is selected from the structure shown in Q2, A3=O, R1=CH(CH3)2, R2=CH3, R5=CH3, Compound 223: Q is selected from the structure shown in Q2, A3=O, R1=CH3, R2=CH3, R4=CH3, R5=CH3, Compound 224: Q is selected from the structure shown in Q2, A3=O, R1=CH2CH3, R2=CH3, R4=CH3, R5=CH3, Compound 225: Q is selected from the structure shown in Q2, A3=O, R1=CH(CH3)2, R2=CH3, R4=CH3, R5=CH3, Compound 226: Q is selected from the structure shown in Q2, A3=O, R1=CH(CH3)2, R2=CH3, R5=CH3, Compound 227: Q is selected from the structure shown in Q2, A3=O, R1=CH3, R2=CH3, R4=CH3, R5=CH3, Compound 228: Q is selected from the structure shown in Q2, A3=O, R1=CH2CH3, R2=CH3, R4=CH3, R5=CH3, Compound 229: Q is selected from the structure shown in Q2, A3=O, R1=CH(CH3)2, R2=CH3, R4=CH3, R5=CH3, Compound 230: Q is selected from the structure shown in Q2, A3=O, R1=CH(CH3)2, R2=CH3, R5=CH3, Compound 231: Q is selected from the structure shown in Q2, A3=O, R1=CH3, R2=CH3, R4=CH3, R5=CH3, Compound 232: Q is selected from the structure shown in Q2, A3=S, R1=CH3, R2=CH3, R4=CH3, R5=CH3, Compound 233: Q is selected from the structure shown in Q2, A3=O, R1=CH2CH3, R2=CH3, R4=CH3, R5=CH3, Compound 234: Q is selected from the structure shown in Q2, A3=O, R1=CH(CH3)2, R2=CH3, R4=CH3, R5=CH3, Compound 235: Q is selected from the structure shown in Q2, A3=O, R1=CH3, R2=CH3, R5=CH3, Compound 236: Q is selected from the structure shown in Q2, A3=O, R1=CH2CH3, R2=CH3, R5=CH3, Compound 237: Q is selected from the structure shown in Q2, A3=O, R1=CH(CH3)2, R2=CH3, R5=CH3, Compound 238: Q is selected from the structure shown in Q2, A3=O, R1=CH3, R2=CH3, R4=CH3, R5=CH3, Compound 239: Q is selected from the structure shown in Q2, A3=O, R1=CH2CH3, R2=CH3, R4=CH3, R5=CH3, Compound 240: Q is selected from the structure shown in Q2, A3=O, R1=CH(CH3)2, R2=CH3, R4=CH3, R5=CH3, Compound 241: Q is selected from the structure shown in Q2, A3=O, R1=CH3, R2=CH3, R5=CH3, Compound 242: Q is selected from the structure shown in Q2, A3=O, R1=CH2CH3, R2=CH3, R5=CH3, Compound 243: Q is selected from the structure shown in Q2, A3=O, R1=CH(CH3)2, R2=CH3, R5=CH3, Compound 244: Q is selected from the structure shown in Q2, A3=O, R1=CH3, R2=CH3, R4=CH3, R5=CH3, Compound 245: Q is selected from the structure shown in Q2, A3=S, R1=CH3, R2=CH3, R4=CH3, R5=CH3, Compound 246: Q is selected from the structure shown in Q2, A3=O, R1=CH(CH3)2, R2=CH3, R4=CH3, R5=CH3, Compound 247: Q is selected from the structure shown in Q2, A3=O, R1=CH3, R2=CH3, R5=CH3, Compound 248: Q is selected from the structure shown in Q2, A3=O, R1=CH2CH3, R2=CH3, R5=CH3, Compound 249: Q is selected from the structure shown in Q2, A3=O, R1=CH(CH3)2, R2=CH3, R5=CH3, Compound 250: Q is selected from the structure shown in Q2, A3=O, R1=CH3, R2=CH3, R4=CH3, R5=CH3, Compound 251: Q is selected from the structure shown in Q2, A3=O, R1=CH(CH3)2, R2=CH3, R4=CH3, R5=CH3, Compound 252: Q is selected from the structure shown in Q2, A3=O, R1=CH3, R2=CH3, R5=CH3, Compound 253: Q is selected from the structure shown in Q2, A3=O, R1=CH2CH3, R2=CH3, R5=CH3, Compound 254: Q is selected from the structure shown in Q2, A3=O, R1=CH(CH3)2, R2=CH3, R5=CH3, Compound 255: Q is selected from the structure shown in Q2, A3=O, R1=CH3, R2=CH3, R4=CH3, R5=CH3, Compound 256: Q is selected from the structure shown in Q2, A3=S, R1=CH3, R2=CH3, R4=CH3, R5=CH3, Compound 257: Q is selected from the structure shown in Q2, A3=O, R1=CH(CH3)2, R2=CH3, R4=CH3, R5=CH3, Compound 258: Q is selected from the structure shown in Q2, A3=O, R1=CH3, R2=CH3, R5=CH3, Compound 259: Q is selected from the structure shown in Q2, A3=O, R1=CH2CH3, R2=CH3, R5=CH3, Compound 260: Q is selected from the structure shown in Q2, A3=O, R1=CH(CH3)2, R2=CH3, R5=CH3, 8. Use of the oxadiazolone compound or its tautomer according to any one of claims 1 to 7 in controlling weeds.

9. The use according to claim 8, characterized in that The weeds are selected from one or more of broadleaf weeds and grass weeds.

10. A herbicidal composition comprising the oxadiazolone compound or its tautomer according to any one of claims 1 to 7 and an auxiliary material.

11. A method for controlling weeds, characterized in that: include: Applying the herbicidal composition according to claim 10 to crops.