Oxadiazolone compounds, herbicidal compositions and uses thereof
By substituting the oxadiazole group between the sulfonyl group and Cl on the benzoyl ring of the benzoyl compound, the problem of insufficient crop safety in the prior art is solved, and the consideration of high herbicide activity and high crop safety is achieved.
Patent Information
- Application Number
- CN202410841092.X
- Authority / Receiving Office
- CN · China
- Patent Type
- Patents(China)
- Current Assignee / Owner
- Filing Date
- 2023-11-17
- Publication Date
- 2025-02-28
- Estimated Expiration
- 2043-11-17
AI Technical Summary
The existing benzoyl herbicides have low crop safety when their herbicide activity is high, making it difficult to take into account both high herbicide activity and high crop safety.
Substitution of the group of formula (a) is obtained by using the position between the sulfonyl group and Cl on the benzoyl compound to obtain a oxadiazole compound, which improves herbicidal activity and reduces its toxicity to the crop.
It has achieved excellent herbicidal activity for a variety of weeds, and is safer for crops such as corn and rice, and has the ability to effectively control weeds at low doses.
Smart Images
Figure BDA0004914465420000011 
Figure BDA0004914465420000012 
Figure BDA0004914465420000021
Abstract
Description
[0001] This application is a divisional application of the invention patent application with the invention name of "Oxadiazolone compounds, herbicidal compositions and uses thereof" and application number "202311532732.0". Technical Field
[0002] The present invention relates to the technical field of herbicides, and in particular to an oxadiazolone compound, a herbicidal composition and uses thereof. Background Art
[0003] 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 of benzoyl herbicides. Summary of the invention
[0004] In view of this, the technical problem to be solved by the present invention is to provide an oxadiazolone compound, a composition containing the same and uses thereof. The oxadiazolone compound provided by the present invention has high herbicidal activity and crop safety.
[0005] The present invention provides an oxadiazolone compound or its tautomer represented by formula (I):
[0006]
[0007] In formula (I), R 1 and R 2 independently selected from unsubstituted or substituted by 1 to 3 groups independently selected from the following C 1 ~C 6 Alkyl or C 3 ~C 6 Cycloalkyl: halogen, nitro, C 1 ~C 6 Alkyl, halogenated C 1 ~C 6 Alkyl, C 1 ~C 6 Alkoxy or halogenated C 1 ~C 6 Alkoxyl groups;
[0008] Q is selected from the structure shown by Q1, Q2 or Q3:
[0009]
[0010] Among them, A 1 , A 2 , A 3 , A 4 and A 5Independently selected from O or S;
[0011] R 3 and R 10 independently selected from hydrogen, unsubstituted or substituted by 1 to 3 groups independently selected from the following C 1 ~C 6 Alkyl, C 3 ~C 6 Cycloalkyl, C 1 ~C 6 Alkoxy, phenyl or benzyl: halogen, nitro, C 1 ~C 6 Alkyl, halogenated C 1 ~C 6 Alkyl, C 1 ~C 6 Alkoxy, halogenated C 1 ~C 6 an alkoxy group, a phenyl group or a halogenated phenyl group;
[0012] n is an integer from 1 to 6;
[0013] R 4 is selected from hydrogen, halogen, unsubstituted or substituted by 1 to 3 groups independently selected from the following C 1 ~C 6 Alkyl, C 3 ~C 6 Cycloalkyl or C 1 ~C 6 Alkoxy: halogen, nitro, C 1 ~C 6 Alkyl, halogenated C 1 ~C 6 Alkyl, C 1 ~C 6 Alkoxy or halogenated C 1 ~C 6 Alkoxy;
[0014] R 5 is selected from hydrogen, unsubstituted or substituted by 1 to 3 groups independently selected from the following C 1 ~C 6 Alkyl or C 3 ~C 6 Cycloalkyl: halogen, nitro, C 1 ~C 6 Alkyl, halogenated C 1 ~C 6 Alkyl, C 1 ~C 6 Alkoxy or halogenated C 1 ~C 6 Alkoxy;
[0015] R6 is selected from hydrogen, a structure represented by formula (1), unsubstituted or substituted by 1 to 3 groups independently selected from the following C 1 ~C 6 Alkyl, C 3 ~C 6 Cycloalkyl, C 3 ~C 8 Heterocycloalkyl: halogen, nitro, C 1 ~C 6 Alkyl, halogenated C 1 ~C 6 Alkyl, C 1 ~C 6 Alkoxy or halogenated C 1 ~C 6 Alkoxy;
[0016]
[0017] In formula (1), A 6 Select from N or CR 9 , R 9 is selected from hydrogen, unsubstituted or substituted by 1 to 3 groups independently selected from the following C 1 ~C 6 Alkyl, C 3 ~C 6 Cycloalkyl or C 1 ~C 6 Alkoxy: halogen, nitro, C 1 ~C 6 Alkyl, halogenated C 1 ~C 6 Alkyl, C 1 ~C 6 Alkoxy or halogenated C 1 ~C 6 Alkoxy;
[0018] R 7 and R 8 independently selected from hydrogen, unsubstituted or substituted by 1 to 3 groups independently selected from the following C 1 ~C 6 Alkyl, C 3 ~C 6 Cycloalkyl or C 1 ~C 6 Alkoxy: halogen, nitro, C 1 ~C 6 Alkyl, halogenated C 1 ~C 6 Alkyl, C 1 ~C 6 Alkoxy or halogenated C 1 ~C 6Alkoxy; R 7 and R 8 Not at the same time H;
[0019] Or, R 7 , R 8 With its A 6 Forming a C which is unsubstituted or substituted by 1 to 3 groups independently selected from the following groups and contains 0 to 3 heteroatoms 3 ~C 8 Ring: halogen, nitro, C 1 ~C 6 Alkyl, C 3 ~C 6 Cycloalkyl, halogenated C 1 ~C 6 Alkyl, C 1 ~C 6 Alkoxy or halogenated C 1 ~C 6 The heteroatom is selected from oxygen, sulfur or nitrogen.
[0020] The applicant has found that the oxadiazolone compounds obtained by replacing the position between the sulfonyl group and Cl on the benzene ring of the benzoyl compound with a group of formula (a) not only have excellent herbicidal activity against a variety of weeds, but are also relatively safe for a variety of crops such as corn and rice:
[0021] Group.
[0022] In some specific implementations, in formula (I), R 1 and R 2 independently selected from unsubstituted or substituted by 1 to 3 groups independently selected from the following C 1 ~C 4 Alkyl or C 3 ~C 6 Cycloalkyl: halogen, nitro, C 1 ~C 4 Alkyl, halogenated C 1 ~C 4 Alkyl, C 1 ~C 4 Alkoxy or halogenated C 1 ~C 4 In some specific implementations, R 1 and R 2 Independently selected from -CH 3 、-CH 2 CH 3 、-CH 2 CH 2 CH 3 、-CH(CH 3 )2 、-C(CH 3 ) 3 、-CH 2 CH 2 CH 2 CH 3 , -CF 3 、-CH 2 CF 3 、-CH 2 CH 2 CF 3 、-CH(CF 3 ) 2 ,-C(CF 3 ) 3 、-CHCH 3 CF 3 、-C(CH 3 ) 2 CF 3 or CCH 2 (CF 3 ) 2 ; In some specific implementations, R 1 is selected from methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl or tert-butyl; R 2 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]
[0025] Among them, A 1 , A 2 are independently selected from O or S. In some specific implementations, A 1 , A 2 All are O.
[0026] In the Q1 structure, R 3 Preferably, it is selected from hydrogen, unsubstituted or substituted by 1 to 3 groups independently selected from the following C 1 ~C 4 Alkyl, C 3 ~C 6 Cycloalkyl, C 1 ~C 4 Alkoxy, phenyl or benzyl: halogen, nitro, C 1 ~C 4 Alkyl, halogenated C 1 ~C 4 Alkyl, C 1 ~C 4 Alkoxy, halogenated C 1 ~C4 alkoxy, phenyl or halogenated phenyl; in some specific implementations, R 3 is selected from hydrogen, C1-C4 alkyl, unsubstituted or substituted by 1-3 halogen phenyl, or unsubstituted or substituted by 1-3 halogen benzyl; in some specific implementations, R 3 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.
[0027] In the Q1 structure, n is a substituent R 3 The number is an integer from 1 to 6, and can be 1, 2, 3, 4, 5 or 6, and is preferably 1, 2 or 3.
[0028] In some specific implementations, Q is selected from the structure shown in Q2:
[0029]
[0030] In the Q2 structure, A 3 is selected from O or S. In some specific implementations, A 3 is O.
[0031] In the Q2 structure, R 4 Preferably, it is selected from hydrogen, halogen, unsubstituted or substituted by 1 to 3 groups independently selected from the following C 1 ~C 4 Alkyl, C 3 ~C 6 Cycloalkyl or C 1 ~C 4 Alkoxy: halogen, nitro, C 1 ~C 4 Alkyl, halogenated C 1 ~C 4 Alkyl, C 1 ~C 4 Alkoxy or halogenated C 1 ~C 4 In some specific implementations, R 4 is selected from hydrogen, halogen, C1-C4 alkyl, halogenated C1-C4 alkyl, C3-C6 cycloalkyl or C1-C4 alkoxy. 4 is selected from hydrogen, chlorine, C1-C4 alkyl or C3-C6 cycloalkyl. In some specific implementations, R 4 is selected from hydrogen, methyl, ethyl, isopropyl or cyclopropyl.
[0032] In the Q2 structure, R 5Preferably, it is selected from hydrogen, unsubstituted or substituted by 1 to 3 groups independently selected from the following C 1 ~C 4 Alkyl or C 3 ~C 6 Cycloalkyl: halogen, nitro, C 1 ~C 4 Alkyl, halogenated C 1 ~C 4 Alkyl, C 1 ~C 4 Alkoxy or halogenated C 1 ~C 4 In some specific implementations, R 5 is selected from hydrogen, C1-C4 alkyl, halogenated C1-C4 alkyl or C3-C6 cycloalkyl; in some specific implementations, R 5 Selected from methyl, ethyl or cyclopropyl.
[0033] In the Q2 structure, R 6 Preferably, it is selected from hydrogen, a structure represented by formula (1), unsubstituted or substituted by 1 to 3 groups independently selected from the following C 1 ~C 4 Alkyl, C 3 ~C 6 Cycloalkyl, C 3 ~C 8 Heterocycloalkyl: halogen, nitro, C 1 ~C 4 Alkyl, halogenated C 1 ~C 4 Alkyl, C 1 ~C 4 Alkoxy or halogenated C 1 ~C 4 In some specific implementations, R 6 is selected from hydrogen, the structure represented by formula (1), C 1 ~C 4 Alkyl, C 3 ~C 6 Cycloalkyl, C 3 ~C 8 Heterocycloalkyl or halogenated C 1 ~C 4 of alkyl.
[0034]
[0035] In formula (1), A 6 Select from N or CR 9 , R 9 is selected from hydrogen, unsubstituted or substituted by 1 to 3 groups independently selected from the following C 1 ~C6 Alkyl, C 3 ~C 6 Cycloalkyl or C 1 ~C 6 Alkoxy: halogen, nitro, C 1 ~C 6 Alkyl, halogenated C 1 ~C 6 Alkyl, C 1 ~C 6 Alkoxy or halogenated C 1 ~C 6 In some specific implementations, R 9 Selected from hydrogen, C 1 ~C 4 Alkyl, C 3 ~C 6 Cycloalkyl, C 1 ~C 4 Alkoxy, halogenated C 1 ~C 4 Alkyl or halogenated C 1 ~C 4 In some specific implementations, R 9 is selected from methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl or tert-butyl.
[0036] In formula (1), R 7 and R 8 independently selected from hydrogen, unsubstituted or substituted by 1 to 3 groups independently selected from the following C 1 ~C 6 Alkyl, C 3 ~C 6 Cycloalkyl or C 1 ~C 6 Alkoxy: halogen, nitro, C 1 ~C 6 Alkyl, halogenated C 1 ~C 6 Alkyl, C 1 ~C 6 Alkoxy or halogenated C 1 ~C 6 In some specific implementations, R 7 and R 8 are independently selected from hydrogen, C 1 ~C 4 Alkyl, C 3 ~C 6 Cycloalkyl, C 1 ~C 4 Alkoxy, halogenated C 1 ~C 4Alkyl or halogenated C 1 ~C 4 In some specific implementations, R 7 and R 8 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. 7 and R 8 Not H at the same time.
[0037] In formula (1), R 7 , R 8 Preferably with its A 6 Forming a C which is unsubstituted or substituted by 1 to 3 groups independently selected from the following groups and contains 1 to 3 heteroatoms 3 ~C 8 Ring: halogen, nitro, C 1 ~C 4 Alkyl, C 3 ~C 6 Cycloalkyl, halogenated C 1 ~C 4 Alkyl, C 1 ~C 4 Alkoxy or halogenated C 1 ~C 4 wherein the heteroatom is selected from oxygen, sulfur or nitrogen. In some specific implementations, R 7 , R 8 Preferably with its A 6 to form a heterocyclic ring, pyrazole ring, furan ring, tetrahydrofuran ring, thiophene ring or tetrahydrothiophene ring which is unsubstituted or substituted by 1 to 3 groups independently selected from the following groups: halogen, nitro, C 1 ~C 4 Alkyl, C 3 ~C 6 Cycloalkyl, halogenated C 1 ~C 4 Alkyl, C 1 ~C 4 Alkoxy or halogenated C 1 ~C 4 In some specific implementations, R 7 , R 8 Preferably with its A 6 This forms a ring as shown in the following structure:
[0038]
[0039] Among them, R 1 , R 3 , R 4 , R6 are independently selected from hydrogen, halogen, C 1 ~C 4 Alkyl, halogenated C 1 ~C 4 Alkyl or C 3 ~C 6 The cycloalkyl group is preferably selected from hydrogen, chlorine, trifluoromethyl, methyl, ethyl, isopropyl or cyclopropyl. 2 , R 5 , R 7 are independently selected from hydrogen, C 1 ~C 4 Alkyl, halogenated C 1 ~C 4 Alkyl or C 3 ~C 6 The cycloalkyl group is preferably selected from hydrogen, methyl, ethyl or cyclopropyl.
[0040] In some specific implementations, R 6 Preferably selected from the following structures:
[0041]
[0042] 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.
[0043] In some specific implementations, Q is selected from the structure shown in Q3:
[0044]
[0045] In the Q3 structure, A 4 and A 5 are independently selected from O or S; in some specific implementations, A 4 Selected from O, A 5 Select from O or S.
[0046] In the Q3 structure, R 10 Preferably, it is selected from hydrogen, unsubstituted or substituted by 1 to 3 groups independently selected from the following C 1 ~C 4 Alkyl, C 3~C 6 Cycloalkyl, C 1 ~C 4 Alkoxy, phenyl or benzyl: halogen, nitro, C 1 ~C 4 Alkyl, halogenated C 1 ~C 4 Alkyl, C 1 ~C 4 Alkoxy, halogenated C 1 ~C 4 alkoxy, phenyl or halogenated phenyl; in some specific implementations, R 10 is selected from hydrogen, C1-C4 alkyl, unsubstituted or substituted by 1-3 halogen phenyl, or unsubstituted or substituted by 1-3 halogen benzyl; 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 10 Selected from H, -CH 3 、-CH 2 CH 3 、-CH 2 CH 2 CH 3 、-CH(CH 3 ) 2 、-C(CH 3 ) 3 、-CH 2 CH 2 CH 2 CH 3 , phenyl, chlorophenyl, dichlorophenyl, C 6 H 5 CH 2 -、C 6 H 4 CHCl 2 - or C 6 H 3 Cl 2 CH 2 -.
[0047] In some specific implementations, Q is selected from the structure shown in Q1-1:
[0048]
[0049] R 3 Selected from H, C 1 ~C 4 Alkyl or C 1 ~C 4 of a halogenated alkyl group.
[0050] In some specific implementations, Q is selected from the structure shown in Q3-1:
[0051]
[0052] R 10 Selected from H, C 1 ~C 4 Alkyl, C 1 ~C 4 haloalkyl, phenyl, halophenyl, phenyl substituted C 1 ~C 4 Alkyl or halophenyl substituted C 1 ~C 4 of alkyl.
[0053] In some specific implementations, Q is selected from the structure shown in Q2-1:
[0054]
[0055] X 1 Selected from C or N, X 2 is selected from C, N, O or S, X 1 and X 2 Not at the same time, it is C;
[0056] R 11 Selected from H, halogen, C 1 ~C 4 Alkyl, C 3 -C 6 Cycloalkyl or C 1 ~C 4 In some specific implementations, R 11 Selected from H, CH 3 CF 3 、-CH 2 CH 3、 Cyclopropyl or Cl.
[0057] m is a substituent R 11 The number of is an integer from 1 to 3;
[0058] R 4 Selected from hydrogen, halogen, C 1 ~C 4 Alkyl, halogenated C 1 ~C 4 Alkyl, C 3 ~C 6 Cycloalkyl, halogenated C 3 ~C 6 Cycloalkyl, C 1 ~C 4Alkoxy, halogenated C 1 ~C 4 Alkoxyl groups;
[0059] R 5 Selected from hydrogen, C 1 ~C 4 Alkyl or halogenated C 1 ~C 4 of alkyl.
[0060] In some specific implementations, the compound is selected from the following:
[0061] Compound 1: Q is selected from the structure shown in Q1-1, R 1 =CH 3 , R 2 =CH 3 , R 3 =H;
[0062] Compound 2: Q is selected from the structure shown in Q1-1, R 1 =CH 3 , R 2 =CH 2 CH 3 , R 3 =H;
[0063] Compound 3: Q is selected from the structure shown in Q1-1, R 1 =CH 3 , R 2 =CH 2 CH 2 CH 3 , R 3 =H;
[0064] Compound 4: Q is selected from the structure shown in Q1-1, R 1 =CH 3 , R 2 =C(CH 3 ) 3 , R 3 =H;
[0065] Compound 5: Q is selected from the structure shown in Q1-1, R 1 =CH 3 , R 2 =CF 3 , R 3 =H;
[0066] Compound 6: Q is selected from the structure shown in Q1-1, R 1 =CH 2 CH 3 , R 2 =CH 3 , R3 =H;
[0067] Compound 7: Q is selected from the structure shown in Q1-1, R 1 =CH 2 CH 3 , R 2 =CH 2 CH 3 , R 3 =H;
[0068] Compound 8: Q is selected from the structure shown in Q1-1, R 1 =CH 2 CH 3 , R 2 =CH 2 CH 2 CH 3 , R 3 =H;
[0069] Compound 9: Q is selected from the structure shown in Q1-1, R 1 =CH 2 CH 3 , R 2 =C(CH 3 ) 3 , R 3 =H;
[0070] Compound 10: Q is selected from the structure shown in Q1-1, R 1 =CH 2 CH 3 , R 2 =CF 3 , R 3 =H;
[0071] Compound 11: Q is selected from the structure shown in Q1-1, R 1 =CH 2 CH 2 CH 3 , R 2 =CH 3 , R 3 =H;
[0072] Compound 12: Q is selected from the structure shown in Q1-1, R 1 =CH 2 CH 2 CH 3 , R 2 =CH 2 CH 3 , R 3 =H;
[0073] Compound 13: Q is selected from the structure shown in Q1-1, R1 =CH 2 CH 2 CH 3 , R 2 =CH 2 CH 2 CH 3 , R 3 =H;
[0074] Compound 14: Q is selected from the structure shown in Q1-1, R 1 =CH 2 CH 2 CH 3 , R 2 =C(CH 3 ) 3 , R 3 =H;
[0075] Compound 15: Q is selected from the structure shown in Q1-1, R 1 =CH 2 CH 2 CH 3 , R 2 =CF 3 , R 3 =H;
[0076] Compound 16: Q is selected from the structure shown in Q1-1, R 1 =CH(CH 3 ) 2 , R 2 =CH 3 , R 3 =H;
[0077] Compound 17: Q is selected from the structure shown in Q1-1, R 1 =CH(CH 3 ) 2 , R 2 =CH 2 CH 3 , R 3 =H;
[0078] Compound 18: Q is selected from the structure shown in Q1-1, R 1 =CH(CH 3 ) 2 , R 2 =CH 2 CH 2 CH 3 , R 3 =H;
[0079] Compound 19: Q is selected from the structure shown in Q1-1, R 1 =CH(CH3 ) 2 , R 2 =C(CH 3 ) 3 , R 3 =H;
[0080] Compound 20: Q is selected from the structure shown in Q1-1, R 1 =CH(CH 3 ) 2 , R 2 =CF 3 , R 3 =H;
[0081] Compound 21: Q is selected from the structure shown in Q1-1, R 1 =CH 2 CH 2 CH 2 CH 3 , R 2 =CH 3 , R 3 =H;
[0082] Compound 22: Q is selected from the structure shown in Q1-1, R 1 =CH 2 CH 2 CH 2 CH 3 , R 2 =CH 2 CH 3 , R 3 =H;
[0083] Compound 23: Q is selected from the structure shown in Q1-1, R 1 =CH 2 CH 2 CH 2 CH 3 , R 2 =CH 2 CH 2 CH 3 , R 3 =H;
[0084] Compound 24: Q is selected from the structure shown in Q1-1, R 1 =CH 2 CH 2 CH 2 CH 3 , R 2 =C(CH 3 ) 3 , R 3 =H;
[0085] Compound 25: Q is selected from the structure shown in Q1-1, R 1 =CH 2 CH 2 CH 2 CH 3 , R 2 =CF 3 , R 3 =H;
[0086] Compound 26: Q is selected from the structure shown in Q1-1, R 1 =C(CH 3 ) 3 , R 2 =CH 3 , R 3 =H;
[0087] Compound 27: Q is selected from the structure shown in Q1-1, R 1 =C(CH 3 ) 3 , R 2 =CH 2 CH 3 , R 3 =H;
[0088] Compound 28: Q is selected from the structure shown in Q1-1, R 1 =C(CH 3 ) 3 , R 2 =CH 2 CH 2 CH 3 , R 3 =H;
[0089] Compound 29: Q is selected from the structure shown in Q1-1, R 1 =C(CH 3 ) 3 , R 2 =C(CH 3 ) 3 , R 3 =H;
[0090] Compound 30: Q is selected from the structure shown in Q1-1, R 1 =C(CH 3 ) 3 , R 2 =CF 3 , R 3 =H;
[0091] Compound 31: Q is selected from the structure shown in Q3, R 1 =CH 3 , R 2 =CH3 , A 4 =O,A 5 =O,R 10 =CH 3 ;
[0092] Compound 32: Q is selected from the structure shown in Q3, R 1 =CH 3 , R 2 =CH 3 , A 4 =O,A 5 =O,R 10 =CH 2 CH 3 ;
[0093] Compound 33: Q is selected from the structure shown in Q3, R 1 =CH 3 , R 2 =CH 3 , A 4 =O,A 5 =O,R 10 =CH 2 CH 2 CH 3 ;
[0094] Compound 34: Q is selected from the structure shown in Q3, R 1 =CH 3 , R 2 =CH 3 , A 4 =O,A 5 =O,R 10 =CH(CH 3 ) 2 ;
[0095] Compound 35: Q is selected from the structure shown in Q3, R 1 =CH 3 , R 2 =CH 3 , A 4 =O,A 5 =O,R 10 =CH 2 CH 2 CH 2 CH 3 ;
[0096] Compound 36: Q is selected from the structure shown in Q3, R 1 =CH 3 , R 2 =CH 3 , A 4 =O,A 5=O,R 10 =C(CH 3 ) 3 ;
[0097] Compound 37: Q is selected from the structure shown in Q3, R 1 =CH 3 , R 2 =CH 3 , A 4 =O,A 5 =O,
[0098] Compound 38: Q is selected from the structure shown in Q3, R 1 =CH 3 , R 2 =CH 3 , A 4 =O,A 5 =O,
[0099] Compound 39: Q is selected from the structure shown in Q3, R 1 =CH 3 , R 2 =CH 3 , A 4 =O,A 5 =O,
[0100] Compound 40: Q is selected from the structure shown in Q3, R 1 =CH 3 , R 2 =CH 3 , A 4 =O,A 5 =O,
[0101] Compound 41: Q is selected from the structure shown in Q3, R 1 =CH 3 , R 2 =CH 3 , A 4 =O,A 5 =O,
[0102] Compound 42: Q is selected from the structure shown in Q3, R 1 =CH 3 , R 2 =CH 3 , A 4 =O,A 5 =O,
[0103] Compound 43: Q is selected from the structure shown in Q3, R 1 =CH 3 , R 2 =CH 3 , A 4 =O,A 5 =O,
[0104] Compound 44: Q is selected from the structure shown in Q3, R 1 =CH 3 , R 2 =CH 3 , A 4 =O,A 5 =S, R 10 =CH 3 ;
[0105] Compound 45: Q is selected from the structure shown in Q3, R 1 =CH 3 , R 2 =CH 3 , A 4 =O,A 5 =S, R 10 =CH 2 CH 3 ;
[0106] Compound 46: Q is selected from the structure shown in Q3, R 1 =CH 3 , R 2 =CH 3 , A 4 =O,A 5 =S, R 10 =CH 2 CH 2 CH 3 ;
[0107] Compound 47: Q is selected from the structure shown in Q3, R 1 =CH 3 , R 2 =CH 3 , A 4 =O,A 5 =S, R 10 =CH(CH 3 ) 2 ;
[0108] Compound 48: Q is selected from the structure shown in Q3, R 1 =CH 3 , R 2 =CH 3 , A 4 =O,A5 =S, R 10 =CH 2 CH 2 CH 2 CH 3 ;
[0109] Compound 49: Q is selected from the structure shown in Q3, R 1 =CH 3 , R 2 =CH 3 , A 4 =O,A 5 =S, R 10 =C(CH 3 ) 3 ;
[0110] Compound 50: Q is selected from the structure shown in Q3, R 1 =CH 3 , R 2 =CH 3 , A 4 =O,A 5 =S,
[0111] Compound 51: Q is selected from the structure shown in Q3, R 1 =CH 3 , R 2 =CH 3 , A 4 =O,A 5 =S,
[0112] Compound 52: Q is selected from the structure shown in Q3, R 1 =CH 3 , R 2 =CH 3 , A 4 =O,A 5 =S,
[0113] Compound 53: Q is selected from the structure shown in Q3, R 1 =CH 3 , R 2 =CH 3 , A 4 =O,A 5 =S,
[0114] Compound 54: Q is selected from the structure shown in Q3, R 1 =CH 3 , R 2 =CH 3 , A 4=O,A 5 =S,
[0115] Compound 55: Q is selected from the structure shown in Q3, R 1 =CH 3 , R 2 =CH 3 , A 4 =O,A 5 =S,
[0116] Compound 56: Q is selected from the structure shown in Q2, A 3 =O,R 1 =CH 3 , R 2 =CH 3 , R 4 =H, R 5 =CH 3 , R 6 =H;
[0117] Compound 57: Q is selected from the structure shown in Q2, A 3 =O,R 1 =CH 3 , R 2 =CH 3 , R 4 =H, R 5 =CH 2 CH 3 , R 6 =H;
[0118] Compound 58: Q is selected from the structure shown in Q2, A 3 =O,R 1 =CH 3 , R 2 =CH 3 , R 4 =CH 3 , R 5 =CH 3 , R 6 =H;
[0119] Compound 59: Q is selected from the structure shown in Q2, A 3 =O,R 1 =CH 3 , R 2 =CH 3 , R 4 =CH 3 , R 5 =CH 2 CH 3 , R 6 =H;
[0120] Compound 60: Q is selected from the structure shown in Q2, A 3 =O,R 1 =CH 3 , R 2 =CH 3 , R 4 =CH 2 CH 3 , R 5 =CH 3 , R 6 =H;
[0121] Compound 61: Q is selected from the structure shown in Q2, A 3 =O,R 1 =CH 3 , R 2 =CH 3 , R 4 =CH 2 CH 3 , R 5 =CH 2 CH 3 , R 6 =H;
[0122] Compound 62: Q is selected from the structure shown in Q2, A 3 =O,R 1 =CH 3 , R 2 =CH 3 , R 4 =CH 2 CH 2 CH 3 , R 5 =CH 3 , R 6 =H;
[0123] Compound 63: Q is selected from the structure shown in Q2, A 3 =O,R 1 =CH 3 , R 2 =CH 3 , R 4 =CH 2 CH 2 CH 3 , R 5 =CH 2 CH 3 , R 6 =H;
[0124] Compound 64: Q is selected from the structure shown in Q2, A 3 =O,R 1 =CH3 , R 2 =CH 3 , R 4 =CH(CH 3 ) 2 , R 5 =CH 3 , R 6 =H;
[0125] Compound 65: Q is selected from the structure shown in Q2, A 3 =O,R 1 =CH 3 , R 2 =CH 3 , R 4 =CH(CH 3 ) 2 , R 5 =CH 2 CH 3 , R 6 =H;
[0126] Compound 66: Q is selected from the structure shown in Q2, A 3 =O,R 1 =CH 3 , R 2 =CH 3 , R 4 =CF 3 , R 5 =CH 3 , R 6 =H;
[0127] Compound 67: Q is selected from the structure shown in Q2, A 3 =O,R 1 =CH 3 , R 2 =CH 3 , R 4 =CF 3 , R 5 =CH 2 CH 3 , R 6 =H;
[0128] Compound 68: Q is selected from the structure shown in Q2, A 3 =O,R 1 =CH 3 , R 2 =CH 3 , R 5 =CH 3 , R 6 =H;
[0129] Compound 69: Q is selected from the structure shown in Q2, A 3 =O,R 1 =CH 3 , R 2 =CH 3 , R 5 =CH 2 CH 3 , R 6 =H;
[0130] Compound 70: Q is selected from the structure shown in Q2, A 3 =O,R 1 =CH 2 CH 3 , R 2 =CH 3 , R 4 =H, R 5 =CH 3 , R 6 =H;
[0131] Compound 71: Q is selected from the structure shown in Q2, A 3 =O,R 1 =CH 2 CH 3 , R 2 =CH 3 , R 4 =H, R 5 =CH 2 CH 3 , R 6 =H;
[0132] Compound 72: Q is selected from the structure shown in Q2, A 3 =O,R 1 =CH 2 CH 3 , R 2 =CH 3 , R 4 =CH 3 , R 5 =CH 3 , R 6 =H;
[0133] Compound 73: Q is selected from the structure shown in Q2, A 3 =O,R 1 =CH 2 CH 3 , R 2 =CH 3 , R 4 =CH 3 , R 5 =CH2 CH 3 , R 6 =H;
[0134] Compound 74: Q is selected from the structure shown in Q2, A 3 =O,R 1 =CH 2 CH 3 , R 2 =CH 3 , R 4 =CH 2 CH 3 , R 5 =CH 3 , R 6 =H;
[0135] Compound 75: Q is selected from the structure shown in Q2, A 3 =O,R 1 =CH 2 CH 3 , R 2 =CH 3 , R 4 =CH 2 CH 3 , R 5 =CH 2 CH 3 , R 6 =H;
[0136] Compound 76: Q is selected from the structure shown in Q2, A 3 =O,R 1 =CH 2 CH 3 , R 2 =CH 3 , R 4 =CH 2 CH 2 CH 3 , R 5 =CH 3 , R 6 =H;
[0137] Compound 77: Q is selected from the structure shown in Q2, A 3 =O,R 1 =CH 2 CH 3 , R 2 =CH 3 , R 4 =CH 2 CH 2 CH 3 , R 5 =CH 2 CH3 , R 6 =H;
[0138] Compound 78: Q is selected from the structure shown in Q2, A 3 =O,R 1 =CH 2 CH 3 , R 2 =CH 3 , R 4 =CH(CH 3 ) 2 , R 5 =CH 3 , R 6 =H;
[0139] Compound 79: Q is selected from the structure shown in Q2, A 3 =O,R 1 =CH 2 CH 3 , R 2 =CH 3 , R 4 =CH(CH 3 ) 2 , R 5 =CH 2 CH 3 , R 6 =H;
[0140] Compound 80: Q is selected from the structure shown in Q2, A 3 =O,R 1 =CH 2 CH 3 , R 2 =CH 3 , R 4 =CF 3 , R 5 =CH 3 , R 6 =H;
[0141] Compound 81: Q is selected from the structure shown in Q2, A 3 =O,R 1 =CH 2 CH 3 , R 2 =CH 3 , R 4 =CF 3 , R 5 =CH 2 CH 3 , R 6 =H;
[0142] Compound 82: Q is selected from the structure shown in Q2, A3 =O,R 1 =CH 2 CH 3 , R 2 =CH 3 , R 5 =CH 3 , R 6 =H;
[0143] Compound 83: Q is selected from the structure shown in Q2, A 3 =O,R 1 =CH 2 CH 3 , R 2 =CH 3 , R 5 =CH 2 CH 3 , R 6 =H;
[0144] Compound 84: Q is selected from the structure shown in Q2, A 3 =O,R 1 =CH 2 CH 2 CH 3 , R 2 =CH 3 , R 4 =H, R 5 =CH 3 , R 6 =H;
[0145] Compound 85: Q is selected from the structure shown in Q2, A 3 =O,R 1 =CH 2 CH 2 CH 3 , R 2 =CH 3 , R 4 =H, R 5 =CH 2 CH 3 , R 6 =H;
[0146] Compound 86: Q is selected from the structure shown in Q2, A 3 =O,R 1 =CH 2 CH 2 CH 3 , R 2 =CH 3 , R 4 =CH 3 , R5 =CH 3 , R 6 =H;
[0147] Compound 87: Q is selected from the structure shown in Q2, A 3 =O,R 1 =CH 2 CH 2 CH 3 , R 2 =CH 3 , R 4 =CH 3 , R 5 =CH 2 CH 3 , R 6 =H;
[0148] Compound 88: Q is selected from the structure shown in Q2, A 3 =O,R 1 =CH 2 CH 2 CH 3 , R 2 =CH 3 , R 4 =CH 2 CH 3 , R 5 =CH 3 , R 6 =H;
[0149] Compound 89: Q is selected from the structure shown in Q2, A 3 =O,R 1 =CH 2 CH 2 CH 3 , R 2 =CH 3 , R 4 =CH 2 CH 3 , R 5 =CH 2 CH 3 , R 6 =H;
[0150] Compound 90: Q is selected from the structure shown in Q2, A 3 =O,R 1 =CH 2 CH 2 CH 3 , R 2 =CH 3 , R 4 =CH 2 CH 2 CH3 , R 5 =CH 3 , R 6 =H;
[0151] Compound 91: Q is selected from the structure shown in Q2, A 3 =O,R 1 =CH 2 CH 2 CH 3 , R 2 =CH 3 , R 4 =CH 2 CH 2 CH 3 , R 5 =CH 2 CH 3 , R 6 =H;
[0152] Compound 92: Q is selected from the structure shown in Q2, A 3 =O,R 1 =CH 2 CH 2 CH 3 , R 2 =CH 3 , R 4 =CH(CH 3 ) 2 , R 5 =CH 3 , R 6 =H;
[0153] Compound 93: Q is selected from the structure shown in Q2, A 3 =O,R 1 =CH 2 CH 2 CH 3 , R 2 =CH 3 , R 4 =CH(CH 3 ) 2 , R 5 =CH 2 CH 3 , R 6 =H;
[0154] Compound 94: Q is selected from the structure shown in Q2, A 3 =O,R 1 =CH 2 CH 2 CH 3 , R 2 =CH 3 , R4 =CF 3 , R 5 =CH 3 , R 6 =H;
[0155] Compound 95: Q is selected from the structure shown in Q2, A 3 =O,R 1 =CH 2 CH 2 CH 3 , R 2 =CH 3 , R 4 =CF 3 , R 5 =CH 2 CH 3 , R 6 =H;
[0156] Compound 96: Q is selected from the structure shown in Q2, A 3 =O,R 1 =CH 2 CH 2 CH 3 , R 2 =CH 3 , R 5 =CH 3 , R 6 =H;
[0157] Compound 97: Q is selected from the structure shown in Q2, A 3 =O,R 1 =CH 2 CH 2 CH 3 , R 2 =CH 3 , R 5 =CH 2 CH 3 , R 6 =H;
[0158] Compound 98: Q is selected from the structure shown in Q2, A 3 =O,R 1 =CH(CH 3 ) 2 , R 2 =CH 3 , R 4 =H, R 5 =CH 3 , R 6 =H;
[0159] Compound 99: Q is selected from the structure shown in Q2, A 3 =O,R 1 =CH(CH 3 ) 2 , R 2 =CH 3 , R 4 =H, R 5 =CH 2 CH 3 , R 6 =H;
[0160] Compound 100: Q is selected from the structure shown in Q2, A 3 =O,R 1 =CH(CH 3 ) 2 , R 2 =CH 3 , R 4 =CH 3 , R 5 =CH 3 , R 6 =H;
[0161] Compound 101: Q is selected from the structure shown in Q2, A 3 =O,R 1 =CH(CH 3 ) 2 , R 2 =CH 3 , R 4 =CH 3 , R 5 =CH 2 CH 3 , R 6 =H;
[0162] Compound 102: Q is selected from the structure shown in Q2, A 3 =O,R 1 =CH(CH 3 ) 2 , R 2 =CH 3 , R 4 =CH 2 CH 3 , R 5 =CH 3 , R 6 =H;
[0163] Compound 103: Q is selected from the structure shown in Q2, A 3 =O,R 1 =CH(CH 3 ) 2 , R 2=CH 3 , R 4 =CH 2 CH 3 , R 5 =CH 2 CH 3 , R 6 =H;
[0164] Compound 104: Q is selected from the structure shown in Q2, A 3 =O,R 1 =CH(CH 3 ) 2 , R 2 =CH 3 , R 4 =CH 2 CH 2 CH 3 , R 5 =CH 3 , R 6 =H;
[0165] Compound 105: Q is selected from the structure shown in Q2, A 3 =O,R 1 =CH(CH 3 ) 2 , R 2 =CH 3 , R 4 =CH 2 CH 2 CH 3 , R 5 =CH 2 CH 3 , R 6 =H;
[0166] Compound 106: Q is selected from the structure shown in Q2, A 3 =O,R 1 =CH(CH 3 ) 2 , R 2 =CH 3 , R 4 =CH(CH 3 ) 2 , R 5 =CH 3 , R 6 =H;
[0167] Compound 107: Q is selected from the structure shown in Q2, A 3 =O,R 1 =CH(CH 3 ) 2 , R 2 =CH3 , R 4 =CH(CH 3 ) 2 , R 5 =CH 2 CH 3 , R 6 =H;
[0168] Compound 108: Q is selected from the structure shown in Q2, A 3 =O,R 1 =CH(CH 3 ) 2 , R 2 =CH 3 , R 4 =CF 3 , R 5 =CH 3 , R 6 =H;
[0169] Compound 109: Q is selected from the structure shown in Q2, A 3 =O,R 1 =CH(CH 3 ) 2 , R 2 =CH 3 , R 4 =CF 3 , R 5 =CH 2 CH 3 , R 6 =H;
[0170] Compound 110: Q is selected from the structure shown in Q2, A 3 =O,R 1 =CH(CH 3 ) 2 , R 2 =CH 3 , R 5 =CH 3 , R 6 =H;
[0171] Compound 111: Q is selected from the structure shown in Q2, A 3 =O,R 1 =CH(CH 3 ) 2 , R 2 =CH 3 , R 5 =CH 2 CH 3 , R 6 =H;
[0172] Compound 112: Q is selected from the structure shown in Q2, A 3 =O,R 1 =CH 2 CH 2 CH 2 CH 3 , R 2 =CH 3 , R 4 =H, R 5 =CH 3 , R 6 =H;
[0173] Compound 113: Q is selected from the structure shown in Q2, A 3 =O,R 1 =CH 2 CH 2 CH 2 CH 3 , R 2 =CH 3 , R 4 =H, R 5 =CH 2 CH 3 , R 6 =H;
[0174] Compound 114: Q is selected from the structure shown in Q2, A 3 =O,R 1 =CH 2 CH 2 CH 2 CH 3 , R 2 =CH 3 , R 4 =CH 3 , R 5 =CH 3 , R 6 =H;
[0175] Compound 115: Q is selected from the structure shown in Q2, A 3 =O,R 1 =CH 2 CH 2 CH 2 CH 3 , R 2 =CH 3 , R 4 =CH 3 , R 5 =CH 2 CH 3 , R 6 =H;
[0176] Compound 116: Q is selected from the structure shown in Q2, A 3 =O,R 1 =CH 2 CH 2 CH 2 CH 3 , R 2 =CH 3 , R 4 =CH 2 CH 3 , R 5 =CH 3 , R 6 =H;
[0177] Compound 117: Q is selected from the structure shown in Q2, A 3 =O,R 1 =CH 2 CH 2 CH 2 CH 3 , R 2 =CH 3 , R 4 =CH 2 CH 3 , R 5 =CH 2 CH 3 , R 6 =H;
[0178] Compound 118: Q is selected from the structure shown in Q2, A 3 =O,R 1 =CH 2 CH 2 CH 2 CH 3 , R 2 =CH 3 , R 4 =CH 2 CH 2 CH 3 , R 5 =CH 3 , R 6 =H;
[0179] Compound 119: Q is selected from the structure shown in Q2, A 3 =O,R 1 =CH 2 CH 2 CH 2 CH 3 , R 2 =CH 3 , R 4 =CH 2 CH2 CH 3 , R 5 =CH 2 CH 3 , R 6 =H;
[0180] Compound 120: Q is selected from the structure shown in Q2, A 3 =O,R 1 =CH 2 CH 2 CH 2 CH 3 , R 2 =CH 3 , R 4 =CH(CH 3 ) 2 , R 5 =CH 3 , R 6 =H;
[0181] Compound 121: Q is selected from the structure shown in Q2, A 3 =O,R 1 =CH 2 CH 2 CH 2 CH 3 , R 2 =CH 3 , R 4 =CH(CH 3 ) 2 , R 5 =CH 2 CH 3 , R 6 =H;
[0182] Compound 122: Q is selected from the structure shown in Q2, A 3 =O,R 1 =CH 2 CH 2 CH 2 CH 3 , R 2 =CH 3 , R 4 =CF 3 , R 5 =CH 3 , R 6 =H;
[0183] Compound 123: Q is selected from the structure shown in Q2, A 3 =O,R 1 =CH 2 CH 2 CH 2CH 3 , R 2 =CH 3 , R 4 =CF 3 , R 5 =CH 2 CH 3 , R 6 =H;
[0184] Compound 124: Q is selected from the structure shown in Q2, A 3 =O,R 1 =CH 2 CH 2 CH 2 CH 3 , R 2 =CH 3 , R 5 =CH 3 , R 6 =H;
[0185] Compound 125: Q is selected from the structure shown in Q2, A 3 =O,R 1 =CH 2 CH 2 CH 2 CH 3 , R 2 =CH 3 , R 5 =CH 2 CH 3 , R 6 =H;
[0186] Compound 126: Q is selected from the structure shown in Q2, A 3 =O,R 1 =C(CH 3 ) 3 , R 2 =CH 3 , R 4 =H, R 5 =CH 3 , R 6 =H;
[0187] Compound 127: Q is selected from the structure shown in Q2, A 3 =O,R 1 =C(CH 3 ) 3 , R 2 =CH 3 , R 4 =H, R 5 =CH2 CH 3 , R 6 =H;
[0188] Compound 128: Q is selected from the structure shown in Q2, A 3 =O,R 1 =C(CH 3 ) 3 , R 2 =CH 3 , R 4 =CH 3 , R 5 =CH 3 , R 6 =H;
[0189] Compound 129: Q is selected from the structure shown in Q2, A 3 =O,R 1 =C(CH 3 ) 3 , R 2 =CH 3 , R 4 =CH 3 , R 5 =CH 2 CH 3 , R 6 =H;
[0190] Compound 130: Q is selected from the structure shown in Q2, A 3 =O,R 1 =C(CH 3 ) 3 , R 2 =CH 3 , R 4 =CH 2 CH 3 , R 5 =CH 3 , R 6 =H;
[0191] Compound 131: Q is selected from the structure shown in Q2, A 3 =O,R 1 =C(CH 3 ) 3 , R 2 =CH 3 , R 4 =CH 2 CH 3 , R 5 =CH 2 CH 3 , R 6 =H;
[0192] Compound 132: Q is selected from the structure shown in Q2, A 3 =O,R 1 =C(CH 3 ) 3 , R 2 =CH 3 , R 4 =CH 2 CH 2 CH 3 , R 5 =CH 3 , R 6 =H;
[0193] Compound 133: Q is selected from the structure shown in Q2, A 3 =O,R 1 =C(CH 3 ) 3 , R 2 =CH 3 , R 4 =CH 2 CH 2 CH 3 , R 5 =CH 2 CH 3 , R 6 =H;
[0194] Compound 134: Q is selected from the structure shown in Q2, A 3 =O,R 1 =C(CH 3 ) 3 , R 2 =CH 3 , R 4 =CH(CH 3 ) 2 , R 5 =CH 3 , R 6 =H;
[0195] Compound 135: Q is selected from the structure shown in Q2, A 3 =O,R 1 =C(CH 3 ) 3 , R 2 =CH 3 , R 4 =CH(CH 3 ) 2 , R 5 =CH 2 CH 3 , R 6 =H;
[0196] Compound 136: Q is selected from the structure shown in Q2, A 3 =O,R 1 =C(CH 3 ) 3 , R 2 =CH 3 , R 4 =CF 3 , R 5 =CH 3 , R 6 =H;
[0197] Compound 137: Q is selected from the structure shown in Q2, A 3 =O,R 1 =C(CH 3 ) 3 , R 2 =CH 3 , R 4 =CF 3 , R 5 =CH 2 CH 3 , R 6 =H;
[0198] Compound 138: Q is selected from the structure shown in Q2, A 3 =O,R 1 =C(CH 3 ) 3 , R 2 =CH 3 , R 5 =CH 3 , R 6 =H;
[0199] Compound 139: Q is selected from the structure shown in Q2, A 3 =O,R 1 =C(CH 3 ) 3 , R 2 =CH 3 , R 5 =CH 2 CH 3 , R 6 =H;
[0200] Compound 140: Q is selected from the structure shown in Q2, A 3 =S, R 1 =CH 3 , R 2 =CH 3 , R 4 =CH 3 , R5 =CH 3 , R 6 =(CH 3 CH 2 ) 2 NCO;
[0201] Compound 141: Q is selected from the structure shown in Q2, A 3 =O,R 1 =CH 3 , R 2 =CH 3 , R 4 =CH 3 , R 5 =CH 3 , R 6 =(CH 3 CH 2 CH 2 ) 2 NCO;
[0202] Compound 142: Q is selected from the structure shown in Q2, A 3 =O,R 1 =CH 2 CH 3 , R 2 =CH 3 , R 4 =CH 3 , R 5 =CH 3 , R 6 =(CH 3 CH 2 CH 2 ) 2 NCO;
[0203] Compound 143: Q is selected from the structure shown in Q2, A 3 =O,R 1 =CH(CH 3 ) 2 , R 2 =CH 3 , R 4 =CH 3 , R 5 =CH 3 , R 6 =(CH 3 CH 2 CH 2 ) 2 NCO;
[0204] Compound 144: Q is selected from the structure shown in Q2, A 3 =O,R 1 =CH3 , R 2 =CH 3 , R 5 =CH 3 , R 6 =(CH 3 CH 2 CH 2 ) 2 NCO;
[0205] Compound 145: Q is selected from the structure shown in Q2, A 3 =S, R 1 =CH 3 , R 2 =CH 3 , R 4 =CH 3 , R 5 =CH 3 , R 6 =(CH 3 OCH 2 CH 2 ) 2 NCO;
[0206] Compound 146: Q is selected from the structure shown in Q2, A 3 =S, R 1 =CH 3 , R 2 =CH 3 , R 4 =CH 3 , R 5 =CH 3 ,
[0207]
[0208] Compound 147: Q is selected from the structure shown in Q2, A 3 =S, R 1 =CH 3 , R 2 =CH 3 , R 4 =CH 3 , R 5 =CH 3 ,
[0209]
[0210] Compound 148: Q is selected from the structure shown in Q2, A 3 =S, R 1 =CH 3 , R 2 =CH 3, R 4 =CH 3 , R 5 =CH 3 ,
[0211]
[0212] Compound 149: Q is selected from the structure shown in Q2, A 3 =O,R 1 =CH 3 , R 2 =CH 3 , R 4 =CH 3 , R 5 =CH 3 ,
[0213]
[0214] Compound 150: Q is selected from the structure shown in Q2, A 3 =O,R 1 =CH 2 CH 3 , R 2 =CH 3 , R 4 =CH 3 , R 5 =CH 3 ,
[0215]
[0216] Compound 151: Q is selected from the structure shown in Q2, A 3 =O,R 1 =CH(CH 3 ) 2 , R 2 =CH 3 , R 4 =CH 3 , R 5 =CH 3 ,
[0217]
[0218] Compound 152: Q is selected from the structure shown in Q2, A 3 =O,R 1 =CH 3 , R 2 =CH 3 , R 5 =CH 3 ,
[0219]
[0220] Compound 153: Q is selected from the structure shown in Q2, A 3 =O,R 1 =CH 2 CH 3 , R 2 =CH 3 , R 5 =CH 3 ,
[0221]
[0222] Compound 154: Q is selected from the structure shown in Q2, A 3 =O,R 1 =CH 3 , R 2 =CH 3 , R 4 =CH 3 , R 5 =CH 3 ,
[0223]
[0224] Compound 155: Q is selected from the structure shown in Q2, A 3 =O,R 1 =CH 2 CH 3 , R 2 =CH 3 , R 4 =CH 3 , R 5 =CH 3 ,
[0225]
[0226] Compound 156: Q is selected from the structure shown in Q2, A 3 =O,R 1 =CH 2 CH 2 CH 3 , R 2 =CH 3 , R 4 =CH 3 , R 5 =CH 3 ,
[0227]
[0228] Compound 157: Q is selected from the structure shown in Q2, A3 =O,R 1 =CH(CH 3 ) 2 , R 2 =CH 3 , R 4 =CH 3 , R 5 =CH 3 ,
[0229]
[0230] Compound 158: Q is selected from the structure shown in Q2, A 3 =O,R 1 =CH 3 , R 2 =CH 3 , R 4 =H, R 5 =CH 3 ,
[0231]
[0232] Compound 159: Q is selected from the structure shown in Q2, A 3 =O,R 1 =CH 2 CH 3 , R 2 =CH 3 , R 4 =H, R 5 =CH 3 ,
[0233]
[0234] Compound 160: Q is selected from the structure shown in Q2, A 3 =O,R 1 =CH 2 CH 2 CH 3 , R 2 =CH 3 , R 4 =H, R 5 =CH 3 ,
[0235]
[0236] Compound 161: Q is selected from the structure shown in Q2, A 3 =O,R 1 =CH(CH 3 ) 2 , R 2 =CH3 , R 4 =H, R 5 =CH 3 ,
[0237]
[0238] Compound 162: Q is selected from the structure shown in Q2, A 3 =O,R 1 =CH 3 , R 2 =CH 3 , R 5 =CH 3 ,
[0239]
[0240] Compound 163: Q is selected from the structure shown in Q2, A 3 =O,R 1 =CH 2 CH 3 , R 2 =CH 3 , R 5 =CH 3 ,
[0241]
[0242] Compound 164: Q is selected from the structure shown in Q2, A 3 =O,R 1 =CH 2 CH 2 CH 3 , R 2 =CH 3 ,
[0243] Compound 165: Q is selected from the structure shown in Q2, A 3 =O,R 1 =CH(CH 3 ) 2 , R 2 =CH 3 , R 5 =CH 3 ,
[0244]
[0245] Compound 166: Q is selected from the structure shown in Q2, A 3 =O,R 1=CH 3 , R 2 =CH 3 , R 4 =CH 3 , R 5 =CH 3 ,
[0246]
[0247] Compound 167: Q is selected from the structure shown in Q2, A 3 =O,R 1 =CH 2 CH 3 , R 2 =CH 3 , R 4 =CH 3 , R 5 =CH 3 ,
[0248]
[0249] Compound 168: Q is selected from the structure shown in Q2, A 3 =O,R 1 =CH 2 CH 2 CH 3 , R 2 =CH 3 , R 4 =CH 3 , R 5 =CH 3 ,
[0250]
[0251] Compound 169: Q is selected from the structure shown in Q2, A 3 =O,R 1 =CH(CH 3 ) 2 , R 2 =CH 3 , R 4 =CH 3 , R 5 =CH 3 ,
[0252]
[0253] Compound 170: Q is selected from the structure shown in Q2, A 3 =O,R 1 =CH 3 , R 2 =CH3 , R 4 =H, R 5 =CH 3 ,
[0254]
[0255] Compound 171: Q is selected from the structure shown in Q2, A 3 =O,R 1 =CH 2 CH 3 , R 2 =CH 3 , R 4 =H, R 5 =CH 3 ,
[0256] Compound 172: Q is selected from the structure shown in Q2, A 3 =O,R 1 =CH 2 CH 2 CH 3 , R 2 =CH 3 , R 4 =H, R 5 =CH 3 ,
[0257] Compound 173: Q is selected from the structure shown in Q2, A 3 =O,R 1 =CH(CH 3 ) 2 , R 2 =CH 3 , R 4 =H, R 5 =CH 3 ,
[0258] Compound 174: Q is selected from the structure shown in Q2, A 3 =O,R 1 =CH 3 , R 2 =CH 3 , R 5 =CH 3 ,
[0259] Compound 175: Q is selected from the structure shown in Q2, A 3 =O,R 1 =CH 2 CH 3 , R2 =CH 3 , R 5 =CH 3 ,
[0260] Compound 176: Q is selected from the structure shown in Q2, A 3 =O,R 1 =CH 2 CH 2 CH 3 , R 2 =CH 3 , R 5 =CH 3 ,
[0261] Compound 177: Q is selected from the structure shown in Q2, A 3 =O,R 1 =CH(CH 3 ) 2 , R 2 =CH 3 , R 5 =CH 3 ,
[0262] Compound 178: Q is selected from the structure shown in Q2, A 3 =O,R 1 =CH 3 , R 2 =CH 3 , R 4 =CH 3 , R 5 =CH 3 ,
[0263]
[0264] Compound 179: Q is selected from the structure shown in Q2, A 3 =O,R 1 =CH 2 CH 2 CH 3 , R 2 =CH 3 , R 4 =CH 3 , R 5 =CH 3 ,
[0265] Compound 180: Q is selected from the structure shown in Q2, A 3=O,R 1 =CH 3 , R 2 =CH 3 , R 4 =H, R 5 =CH 3 ,
[0266]
[0267] Compound 181: Q is selected from the structure shown in Q2, A 3 =O,R 1 =CH 2 CH 2 CH 3 , R 2 =CH 3 , R 4 =H, R 5 =CH 3 ,
[0268] Compound 182: Q is selected from the structure shown in Q2, A 3 =O,R 1 =CH 3 , R 2 =CH 3 , R 5 =CH 3 ,
[0269] Compound 183: Q is selected from the structure shown in Q2, A 3 =O,R 1 =CH 2 CH 2 CH 3 , R 2 =CH 3 , R 5 =CH 3 ,
[0270] Compound 184: Q is selected from the structure shown in Q2, A 3 =O,R 1 =CH 2 CH 3 , R 2 =CH 3 , R 4 =CH 3 , R 5 =CH 3 ,
[0271] Compound 185: Q is selected from the structure shown in Q2, A 3 =O,R 1 =CH(CH 3 ) 2 , R 2 =CH 3 , R 4 =CH 3 , R 5 =CH 3 ,
[0272] Compound 186: Q is selected from the structure shown in Q2, A 3 =O,R 1 =CH 2 CH 3 , R 2 =CH 3 , R 4 =H, R 5 =CH 3 ,
[0273] Compound 187: Q is selected from the structure shown in Q2, A 3 =O,R 1 =CH(CH 3 ) 2 , R 2 =CH 3 , R 4 =H, R 5 =CH 3 ,
[0274] Compound 188: Q is selected from the structure shown in Q2, A 3 =O,R 1 =CH 2 CH 3 , R 2 =CH 3 , R 5 =CH 3 ,
[0275] Compound 189: Q is selected from the structure shown in Q2, A 3 =O,R 1 =CH(CH 3 ) 2 , R 2 =CH 3 , R 5 =CH 3 ,
[0276] Compound 190: Q is selected from the structure shown in Q2, A 3 =O,R 1 =CH 2 CH 3 , R 2 =CH 3 , R 4 =CH 3 , R 5 =CH2CH 3 ,
[0277] Compound 191: Q is selected from the structure shown in Q2, A 3 =O,R 1 =CH 3 , R 2 =CH 3 , R 4 =H, R 5 =CH 2 CH 3 ,
[0278] Compound 192: Q is selected from the structure shown in Q2, A 3 =O,R 1 =CH 2 CH 2 CH 3 , R 2 =CH 3 , R 5 =CH 2 CH 3 ,
[0279] Compound 193: Q is selected from the structure shown in Q2, A 3 =O,R 1 =CH(CH 3 ) 2 , R 2 =CH 3 , R 5 =CH 2 CH 3 , Compound 194: Q is selected from the structure shown in Q2, A 3 =O,R 1 =CH 3 , R 2 =CH 3 , R 4 =CH 3 , R 5 =CH 3 ,
[0280]
[0281] Compound 195: Q is selected from the structure shown in Q2, A 3 =O,R 1 =CH 2 CH 3 , R 2 =CH 3 , R 4 =CH 3 , R 5 =CH 3 ,
[0282]
[0283] Compound 196: Q is selected from the structure shown in Q2, A 3 =O,R 1 =CH 2 CH 2 CH 3 , R 2 =CH 3 , R 4 =CH 3 , R 5 =CH 3 ,
[0284]
[0285] Compound 197: Q is selected from the structure shown in Q2, A 3 =O,R 1 =CH(CH 3 ) 2 , R 2 =CH 3 , R 4 =CH 3 , R 5 =CH 3 ,
[0286]
[0287] Compound 198: Q is selected from the structure shown in Q2, A 3 =O,R 1 =CH 3 , R 2 =CH 3 , R 4 =H, R 5 =CH 3 ,
[0288]
[0289] Compound 199: Q is selected from the structure shown in Q2, A 3 =O,R 1 =CH 2 CH 3 , R 2 =CH 3 , R 4 =H, R 5 =CH 3 ,
[0290]
[0291] Compound 200: Q is selected from the structure shown in Q2, A 3 =O,R 1 =CH(CH 3 ) 2 , R 2 =CH 3 , R 4 =H, R 5 =CH 3 ,
[0292]
[0293] Compound 201: Q is selected from the structure shown in Q2, A 3 =O,R 1 =CH 3 , R 2 =CH 3 , R 5 =CH 3 ,
[0294]
[0295] Compound 202: Q is selected from the structure shown in Q2, A 3 =O,R 1 =CH 2 CH 3 , R 2 =CH 3 , R 5 =CH 3 ,
[0296]
[0297] Compound 203: Q is selected from the structure shown in Q2, A 3 =O,R 1 =CH(CH 3 ) 2 , R 2 =CH 3, R 5 =CH 3 ,
[0298]
[0299] Compound 204: Q is selected from the structure shown in Q2, A 3 =O,R 1 =CH 3 , R 2 =CH 3 , R 4 =CH 3 , R 5 =CH 3 ,
[0300]
[0301] Compound 205: Q is selected from the structure shown in Q2, A 3 =O,R 1 =CH 2 CH 3 , R 2 =CH 3 , R 4 =CH 3 , R 5 =CH 3 ,
[0302]
[0303] Compound 206: Q is selected from the structure shown in Q2, A 3 =O,R 1 =CH(CH 3 ) 2 , R 2 =CH 3 , R 4 =CH 3 , R 5 =CH 3 ,
[0304]
[0305] Compound 207: Q is selected from the structure shown in Q2, A 3 =O,R 1 =CH 3 , R 2 =CH 3 , R 4 =H, R 5 =CH 3 ,
[0306]
[0307] Compound 208: Q is selected from the structure shown in Q2, A 3 =O,R 1 =CH 2 CH 3 , R 2 =CH 3 , R 4 =H, R 5 =CH 3 ,
[0308]
[0309] Compound 209: Q is selected from the structure shown in Q2, A 3 =O,R 1 =CH 2 CH 2 CH 3 , R 2 =CH 3 , R 4 =H, R 5 =CH 3 ,
[0310]
[0311] Compound 210: Q is selected from the structure shown in Q2, A 3 =O,R 1 =CH(CH 3 ) 2 , R 2 =CH 3 , R 4 =H, R 5 =CH 3 ,
[0312]
[0313] Compound 211: Q is selected from the structure shown in Q2, A 3 =O,R 1 =CH 2 CH 3 , R 2 =CH 3 , R 5 =CH 3 ,
[0314]
[0315] Compound 212: Q is selected from the structure shown in Q2, A 3 =O,R 1 =CH(CH3 ) 2 , R 2 =CH 3 , R 5 =CH 3 ,
[0316]
[0317] Compound 213: Q is selected from the structure shown in Q2, A 3 =O,R 1 =CH 3 , R 2 =CH 3 , R 4 =CH 3 , R 5 =CH 3 ,
[0318]
[0319] Compound 214: Q is selected from the structure shown in Q2, A 3 =O,R 1 =CH 2 CH 3 , R 2 =CH 3 , R 4 =CH 3 , R 5 =CH 3 ,
[0320]
[0321] Compound 215: Q is selected from the structure shown in Q2, A 3 =O,R 1 =CH(CH 3 ) 2 , R 2 =CH 3 , R 4 =CH 3 , R 5 =CH 3 ,
[0322]
[0323] Compound 216: Q is selected from the structure shown in Q2, A 3 =O,R 1 =CH 3 , R 2 =CH 3 , R 5 =CH3 ,
[0324]
[0325] Compound 217: Q is selected from the structure shown in Q2, A 3 =O,R 1 =CH(CH 3 ) 2 , R 2 =CH 3 , R 5 =CH 3 ,
[0326]
[0327] Compound 218: Q is selected from the structure shown in Q2, A 3 =O,R 1 =CH 3 , R 2 =CH 3 , R 4 =CH 3 , R 5 =CH 3 ,
[0328]
[0329] Compound 219: Q is selected from the structure shown in Q2, A 3 =O,R 1 =CH 2 CH 3 , R 2 =CH 3 , R 4 =CH 3 , R 5 =CH 3 ,
[0330]
[0331] Compound 220: Q is selected from the structure shown in Q2, A 3 =O,R 1 =CH(CH 3 ) 2 , R 2 =CH 3 , R 4 =CH 3 , R 5 =CH 3 ,
[0332]
[0333] Compound 221: Q is selected from the structure shown in Q2, A 3 =O,R 1 =CH 3 , R 2 =CH 3 , R 5 =CH 3 ,
[0334]
[0335] Compound 222: Q is selected from the structure shown in Q2, A 3 =O,R 1 =CH(CH 3 ) 2 , R 2 =CH 3 , R 5 =CH 3 ,
[0336]
[0337] Compound 223: Q is selected from the structure shown in Q2, A 3 =O,R 1 =CH 3 , R 2 =CH 3 , R 4 =CH 3 , R 5 =CH 3 ,
[0338]
[0339] Compound 224: Q is selected from the structure shown in Q2, A 3 =O,R 1 =CH 2 CH 3 , R 2 =CH 3 , R 4 =CH 3 , R 5 =CH 3 ,
[0340]
[0341] Compound 225: Q is selected from the structure shown in Q2, A 3 =O,R 1 =CH(CH 3 ) 2 , R 2=CH 3 , R 4 =CH 3 , R 5 =CH 3 ,
[0342]
[0343] Compound 226: Q is selected from the structure shown in Q2, A 3 =O,R 1 =CH(CH 3 ) 2 , R 2 =CH 3 , R 5 =CH 3 ,
[0344]
[0345] Compound 227: Q is selected from the structure shown in Q2, A 3 =O,R 1 =CH 3 , R 2 =CH 3 , R 4 =CH 3 , R 5 =CH 3 ,
[0346]
[0347] Compound 228: Q is selected from the structure shown in Q2, A 3 =O,R 1 =CH 2 CH 3 , R 2 =CH 3 , R 4 =CH 3 , R 5 =CH 3 ,
[0348]
[0349] Compound 229: Q is selected from the structure shown in Q2, A 3 =O,R 1 =CH(CH 3 ) 2 , R 2 =CH 3 , R 4 =CH 3 , R 5 =CH3 ,
[0350]
[0351] Compound 230: Q is selected from the structure shown in Q2, A 3 =O,R 1 =CH(CH 3 ) 2 , R 2 =CH 3 , R 5 =CH 3 ,
[0352]
[0353] Compound 231: Q is selected from the structure shown in Q2, A 3 =O,R 1 =CH 3 , R 2 =CH 3 , R 4 =CH 3 , R 5 =CH 3 ,
[0354]
[0355] Compound 232: Q is selected from the structure shown in Q2, A 3 =S, R 1 =CH 3 , R 2 =CH 3 , R 4 =CH 3 , R 5 =CH 3 ,
[0356]
[0357] Compound 233: Q is selected from the structure shown in Q2, A 3 =O,R 1 =CH 2 CH 3 , R 2 =CH 3 , R 4 =CH 3 , R 5 =CH 3 ,
[0358]
[0359] Compound 234: Q is selected from the structure shown in Q2, A 3 =O,R 1 =CH(CH 3 ) 2 , R 2 =CH 3 , R 4 =CH 3 , R 5 =CH 3 ,
[0360]
[0361] Compound 235: Q is selected from the structure shown in Q2, A 3 =O,R 1 =CH 3 , R 2 =CH 3 , R 5 =CH 3 ,
[0362]
[0363] Compound 236: Q is selected from the structure shown in Q2, A 3 =O,R 1 =CH 2 CH 3 , R 2 =CH 3 , R 5 =CH 3 ,
[0364]
[0365] Compound 237: Q is selected from the structure shown in Q2, A 3 =O,R 1 =CH(CH 3 ) 2 , R 2 =CH 3 , R 5 =CH 3 ,
[0366]
[0367] Compound 238: Q is selected from the structure shown in Q2, A 3 =O,R 1 =CH 3 , R 2 =CH 3 , R 4=CH 3 , R 5 =CH 3 ,
[0368]
[0369] Compound 239: Q is selected from the structure shown in Q2, A 3 =O,R 1 =CH 2 CH 3 , R 2 =CH 3 , R 4 =CH 3 , R 5 =CH 3 ,
[0370]
[0371] Compound 240: Q is selected from the structure shown in Q2, A 3 =O,R 1 =CH(CH 3 ) 2 , R 2 =CH 3 , R 4 =CH 3 , R 5 =CH 3 ,
[0372]
[0373] Compound 241: Q is selected from the structure shown in Q2, A 3 =O,R 1 =CH 3 , R 2 =CH 3 , R 5 =CH 3 ,
[0374]
[0375] Compound 242: Q is selected from the structure shown in Q2, A 3 =O,R 1 =CH 2 CH 3 , R 2 =CH 3 , R 5 =CH 3 ,
[0376]
[0377] Compound 243: Q is selected from the structure shown in Q2, A 3 =O,R 1 =CH(CH 3 ) 2 , R 2 =CH 3 , R 5 =CH 3 ,
[0378]
[0379] Compound 244: Q is selected from the structure shown in Q2, A 3 =O,R 1 =CH 3 , R 2 =CH 3 , R 4 =CH 3 , R 5 =CH 3 ,
[0380]
[0381] Compound 245: Q is selected from the structure shown in Q2, A 3 =S, R 1 =CH 3 , R 2 =CH 3 , R 4 =CH 3 , R 5 =CH 3 ,
[0382]
[0383] Compound 246: Q is selected from the structure shown in Q2, A 3 =O,R 1 =CH(CH 3 ) 2 , R 2 =CH 3 , R 4 =CH 3 , R 5 =CH 3 ,
[0384]
[0385] Compound 247: Q is selected from the structure shown in Q2, A 3 =O,R 1 =CH 3, R 2 =CH 3 , R 5 =CH 3 ,
[0386]
[0387] Compound 248: Q is selected from the structure shown in Q2, A 3 =O,R 1 =CH 2 CH 3 , R 2 =CH 3 , R 5 =CH 3 ,
[0388]
[0389] Compound 249: Q is selected from the structure shown in Q2, A 3 =O,R 1 =CH(CH 3 ) 2 , R 2 =CH 3 , R 5 =CH 3 ,
[0390]
[0391] Compound 250: Q is selected from the structure shown in Q2, A 3 =O,R 1 =CH 3 , R 2 =CH 3 , R 4 =CH 3 , R 5 =CH 3 ,
[0392]
[0393] Compound 251: Q is selected from the structure shown in Q2, A 3 =O,R 1 =CH(CH 3 ) 2 , R 2 =CH 3 , R 4 =CH 3 , R 5 =CH 3 ,
[0394]
[0395] Compound 252: Q is selected from the structure shown in Q2, A 3 =O,R 1 =CH 3 , R 2 =CH 3 , R 5 =CH 3 ,
[0396]
[0397] Compound 253: Q is selected from the structure shown in Q2, A 3 =O,R 1 =CH 2 CH 3 , R 2 =CH 3 , R 5 =CH 3 ,
[0398]
[0399] Compound 254: Q is selected from the structure shown in Q2, A 3 =O,R 1 =CH(CH 3 ) 2 , R 2 =CH 3 , R 5 =CH 3 ,
[0400]
[0401] Compound 255: Q is selected from the structure shown in Q2, A 3 =O,R 1 =CH 3 , R 2 =CH 3 , R 4 =CH 3 , R 5 =CH 3 ,
[0402]
[0403] Compound 256: Q is selected from the structure shown in Q2, A 3 =S, R 1 =CH 3 , R2 =CH 3 , R 4 =CH 3 , R 5 =CH 3 ,
[0404]
[0405] Compound 257: Q is selected from the structure shown in Q2, A 3 =O,R 1 =CH(CH 3 ) 2 , R 2 =CH 3 , R 4 =CH 3 , R 5 =CH 3 ,
[0406]
[0407] Compound 258: Q is selected from the structure shown in Q2, A 3 =O,R 1 =CH 3 , R 2 =CH 3 , R 5 =CH 3 ,
[0408]
[0409] Compound 259: Q is selected from the structure shown in Q2, A 3 =O,R 1 =CH 2 CH 3 , R 2 =CH 3 , R 5 =CH 3 ,
[0410]
[0411] Compound 260: Q is selected from the structure shown in Q2, A 3 =O,R 1 =CH(CH 3 ) 2 , R 2 =CH 3 , R 5 =CH 3 ,
[0412] The compound of formula I or its tautomer has herbicidal activity and can be used to control various weeds in agriculture.
[0413] The present invention also provides use of the oxadiazolone compound or its tautomer described in the above technical solution in preventing and controlling weeds.
[0414] In some specific implementations, the weeds are selected from one or more of broadleaf weeds or grass weeds.
[0415] In some specific implementations, the weeds are selected from one or more of velvetleaf, nightshade, crabgrass and barnyard grass.
[0416] The present invention also provides a herbicidal composition, comprising the oxadiazolone compound or its tautomer as described in the above technical solution and an adjuvant. The present application has no special restrictions on the selection of the adjuvant, and the corresponding adjuvant can be selected according to the desired dosage form. The compound of formula I or its tautomer as the active ingredient can have a weight percentage content of 0.1 to 99%, preferably 0.5 to 50%.
[0417] The herbicidal composition of the present invention can be applied in the form of a variety of formulations. The compound of the present invention is usually dissolved or dispersed in a carrier to prepare a formulation so that it is easier to disperse when used as a herbicide. For example, these chemical formulations can be made into wettable powders or emulsifiable concentrates. Therefore, in these compositions, at least one liquid or solid carrier is added, and it is usually necessary to add a suitable surfactant.
[0418] The present invention also provides a method for controlling weeds, comprising:
[0419] The herbicidal composition described in the above technical solution is applied to crops.
[0420] Specifically, the present invention applies a herbicidal effective amount of the herbicidal composition of the present invention to the weeds or the surface of the site where the weeds grow or the growth medium thereof. A more suitable effective dose is 1 gram to 1000 grams per hectare, and a preferred effective dose is 10 to 500 grams per hectare. For certain applications, one or more other herbicides may be added to the herbicidal composition of the present invention, thereby producing additional advantages and effects.
[0421] The applicant replaces the position between the sulfonyl group and Cl on the benzene ring of the benzoyl compound with an oxadiazolone group shown in formula (a) to obtain an oxadiazolone compound, which not only has unexpectedly high herbicidal activity against a variety of weeds, but is also relatively safe for a variety of crops such as corn and rice. Experimental results show that the compound provided by the present invention has good herbicidal activity, can effectively control weeds such as barnyard grass, crabgrass, and ramie at a low dose, obtains a good herbicidal effect, and is relatively safe for crops.
[0422] Group. DETAILED DESCRIPTION
[0423] In this application, the terms used are generally defined as follows:
[0424] Halogen: refers to fluorine, chlorine, bromine or iodine.
[0425] Alkyl: a straight-chain or branched alkyl group, for example, methyl, ethyl, propyl, isopropyl, n-butyl or tert-butyl.
[0426] Cycloalkyl: a substituted or unsubstituted cyclic alkyl group, such as cyclopropyl, cyclopentyl or cyclohexyl, with substituents such as methyl, halogen, etc.
[0427] Haloalkyl: a straight or branched chain 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.
[0428] Alkoxy: A straight or branched chain alkyl group attached to the structure via an oxygen atom.
[0429] Haloalkoxy: 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.
[0430] Alkylamino: A straight or branched chain alkyl group is attached to the structure via a nitrogen atom.
[0431] The haloalkylamino group refers to a straight-chain or branched alkylamino group, in which the hydrogen atoms may be partially or completely substituted by halogen atoms.
[0432] Cycloalkylamino: A substituted or unsubstituted cyclic alkylamino group attached to the structure via a nitrogen atom, such as cyclopentylamino or cyclohexylamino.
[0433] Heterocycle: A cyclic hydrocarbon containing heteroatoms such as N, O or S in the ring. Examples include furan, thiophene, morpholine, cycloheximide, pyrazole or piperidine.
[0434] Heterocyclic Amino: The heterocyclic ring is attached to the structure through the nitrogen atom.
[0435] Tautomers: refer to structural isomers with different energies that can be converted into each other through a low energy barrier. If tautomers are possible (such as in solution), chemical equilibrium of tautomers can be achieved. For example, proton tautomers include interconversions through proton migration, such as keto-enol isomerization and imine-enamine isomerization. In the present invention, depending on external conditions (such as solvent, pH, etc.), there is keto-enol interconversion.
[0436] Some of the compounds of the present invention can be illustrated by the specific compounds listed in Table 1, Table 2 and Table 3, but the present invention is not limited to these compounds.
[0437] Table 1 Specific compounds 1 to 30
[0438]
[0439]
[0440]
[0441] Table 2 Specific compounds 31 to 55
[0442]
[0443]
[0444]
[0445] Table 3 Specific compounds 56 to 260
[0446]
[0447]
[0448]
[0449]
[0450]
[0451]
[0452]
[0453]
[0454]
[0455]
[0456]
[0457]
[0458]
[0459] The 1H-NMR (400MHz, CDCl3 / CD3CN) data of some compounds are as follows:
[0460] Compound 1: 8.16 (d, J = 8.2 Hz, 1H), 7.35 (d, J = 8.2 Hz, 1H), 5.57 (s, 2H), 3.35 (t, J = 15.0 Hz, 3H), 2.82 (t, J = 6.5 Hz, 2H), 2.43 (t, J = 6.5 Hz, 2H), 2.19 (t, J = 15.0 Hz, 3H), 2.08 (q, J = 6.4 Hz, 2H).
[0461] Compound 5: 8.17 (d, J = 8.0 Hz, 1H), 7.40 (d, J = 8.0 Hz, 1H), 5.74 (s, 2H), 3.30 (t, J = 15.1 Hz, 3H), 2.83 (t, J = 6.5 Hz, 2H), 2.42 (t, J = 6.5 Hz, 2H), 2.10-2.04 (m, 2H).
[0462] Compound 6: 8.14-8.08 (m, 1H), 7.37-7.32 (m, 1H), 5.62 (d, J = 67.3 Hz, 2H), 3.53-3.42 (m, 2H), 2.87-2.77 (m, 2H), 2.52-2.35 (m, 2H), 2.17 (d, J = 4.1 Hz, 3H), 2.12-2.01 (m, 2H),
[0463] 1.37-1.30 (m, 3H).
[0464] Compound 9: 8.12 (d, J = 8.2 Hz, 1H), 7.35 (d, J = 8.0 Hz, 1H), 5.58 (d, J = 11.8 Hz, 2H), 3.58 (td, J = 14.6, 7.2 Hz, 2H), 2.87-2.78 (m, 2H), 2.40 (t, J = 6.5 Hz, 2H), 2.11-2.02 (m, 2H), 1.30 (t, J = 7.4 Hz, 3H), 1.22 (s, 9H).
[0465] Compound 10: 8.15-8.09 (m, 1H), 7.42-7.36 (m, 1H), 5.82-5.58 (m, 2H), 3.40 (td, J=14.9, 7.5 Hz, 2H), 2.88-2.76 (m, 2H), 2.47-2.36 (m, 2H), 2.12-2.01 (m, 2H), 1.37-1.29 (m, 3H).
[0466] Compound 11: 8.11 (d, J = 8.2 Hz, 1H), 7.34 (d, J = 8.2 Hz, 1H), 5.53 (s, 2H), 3.43 (t, J = 8.1 Hz, 2H), 2.82 (t, J = 6.3 Hz, 2H), 2.42 (t, J = 6.6 Hz, 2H), 2.21-2.14 (m, 3H), 2.10-2.03 (m, 2H), 1.81-1.75 (m, 2H), 1.07-0.99 (m, 3H).
[0467] Compound 16: 8.09 (d, J = 8.2 Hz, 1H), 7.34 (d, J = 8.2 Hz, 1H), 5.49 (s, ·2H), 3.67 (t, J = 6.7 Hz, 1H), 2.82 (t, J = 6.3 Hz, 2H), 2.42 (t, J = 6.5 Hz, 2H), 2.17 (t, J = 15.0 Hz, 3H), 2.06 (t, J = 6.5 Hz, 2H), 1.36 (d, J = 6.9 Hz, 6H).
[0468] Compound 21: 8.14-8.08 (m, 1H), 7.37-7.31 (m, 1H), 5.75-5.54 (m, 2H), 3.46-3.37 (m, 2H), 2.86-2.78 (m, 2H), 2.48-2.37 (m, 2H), 2.18-2.16 (m, 3H), 2.10-2.03 (m, 2H), 1.78-1.70 (m, 2H), 1.44 (td, J=14.8, 7.4 Hz, 2H), 0.97-0.90 (m, 3H).
[0469] Compound 26: 8.06 (dd, J = 15.0, 6.7 Hz, 1H), 7.37-7.31 (m, 1H), 5.47 (t, J = 53.0 Hz, 2H), 2.87-2.76 (m, 2H), 2.48-2.37 (m, 2H), 2.16 (s, 3H), 2.09-2.01 (m, 2H), 1.39 (s, 9H).
[0470] Compound 45: 8.06 (d, J = 8.2 Hz, 1H), 7.47-7.41 (m, 1H), 5.48 (s, 2H), 3.26 (s, 3H), 2.95-2.86 (m, 4H), 2.38-2.35 (m, 2H), 2.10 (t, J = 4.0 Hz, 3H), 2.07-2.01 (m, 2H), 1.31 (t, J = 7.4 Hz, 3H).
[0471] Compound 46: 8.05-8.09 (1H), 7.47-7.51 (1H), 5.46-5.50 (2H), 3.48-3.57 (1H), 3.24-3.27 (3H), 2.88-2.94 (2H), 2.34-2.41 (2H), 2.09-2.11 (3H), 2.00-2.08 (2H), 1.30-1.35 (6H).
[0472] Compound 47: 8.02-8.14 (1H), 7.35-7.55 (1H), 5.42-5.55 (2H), 3.22-3.33 (3H), 2.78-2.97 (4H), 2.28-2.45 (2H), 2.07-2.13 (3H), 1.96-2.07 (2H), 1.57-1.76 (2H), 0.92-1.09 (3H).
[0473] Compound 48: 8.04-8.09 (1H), 7.42-7.46 (1H), 5.45-5.50 (2H), 3.23-3.27 (3H), 2.83-2.91 (4H), 2.33-2.39 (2H), 2.08-2.11 (3H), 1.99-2.08 (2H), 1.56-1.65 (2H), 1.38-1.46 (2H), 0.86-0.93 (3H).
[0474] Compound 49: 8.07 (d, J = 8.2 Hz, 1H), 7.64 (d, J = 8.2 Hz, 1H), 5.50 (s, 2H), 3.26 (s, 3H), 2.89 (t, J = 5.9 Hz, 2H), 2.42 (t, J = 6.6 Hz, 2H), 2.10 (s, 3H), 2.08-2.04 (m, 2H), 1.36 (d, J = 2.2 Hz, 9H).
[0475] Compound 51: 8.10 (d, J = 8.2 Hz, 1H), 7.50 (d, J = 8.2 Hz, 1H), 7.43-7.37 (m, 4H), 5.50 (s, 2H), 3.27 (s, 3H), 2.39-2.32 (m, 4H), 2.11 (s, 3H), 1.91-1.84 (m, 2H).
[0476] Compound 53: 8.05 (d, J = 8.2 Hz, 1H), 7.42 (d, J = 8.2 Hz, 1H), 7.29-7.24 (m, 5H), 5.47 (s, 2H), 4.12 (s, 2H), 3.25 (s, 3H), 2.89 (t, J = 6.0 Hz, 2H), 2.35 (t, J = 6.7 Hz, 2H), 2.09 (d, J = 4.4 Hz, 3H), 2.04-1.98 (m, 2H).
[0477] Compound 56: 8.18 (d, J = 8.2 Hz, 1H), 7.68 (d, J = 8.2 Hz, 1H), 7.25 (s, 1H), 5.48 (s, 2H), 3.62 (s, 3H), 3.31 (s, 3H), 2.14 (s, 3H).
[0478] Compound 57: 8.18 (d, J = 8.2 Hz, 1H), 7.70-7.66 (m, 1H), 7.27 (s, 1H), 5.49 (s, 2H), 4.01 (td, J = 14.8, 7.5 Hz, 2H), 3.31 (s, 3H), 2.14 (t, J = 4.0 Hz, 3H), 1.36 (t, J = 7.3 Hz, 3H).
[0479] Compound 58: 8.24 (t, J = 4.1 Hz, 1H), 7.53 (d, J = 8.0 Hz, 1H), 5.60 (s, 2H), 3.65 (s, 3H), 3.35 (s, 3H), 2.19 (s, 3H), 1.67 (s, 3H).
[0480] Compound 59: 8.24 (d, J = 8.2 Hz, 1H), 7.53 (d, J = 8.2 Hz, 1H), 5.64-5.58 (m, 2H), 4.01 (q, J = 7.2 Hz, 2H), 3.34 (d, J = 6.9 Hz, 3H), 2.17 (d, J = 7.7 Hz, 3H), 1.67 (s, 3H), 1.43 (t, J = 7.3 Hz, 3H).
[0481] Compound 60: 8.24 (d, J = 8.0 Hz, 1H), 7.54 (d, J = 8.0 Hz, 1H), 5.60 (s, 2H), 3.74 (s, 1H), 3.66 (d, J = 4.9 Hz, 3H), 3.35 (d, J = 3.0 Hz, 3H), 2.19 (s, 3H), 1.99 (d, J = 7.1 Hz, 2H), 0.92 (t, J = 7.4 Hz, 3H).
[0482] Compound 68: 8.18 (d, J = 8.0 Hz, 1H), 7.66 (d, J = 8.2 Hz, 1H), 5.48 (s, 2H), 3.53 (d, J = 11.3 Hz, 3H), 3.28 (s, 3H), 2.12 (s, 3H), 0.93 (s, 1H), 0.58 (d, J = 2.7 Hz, 2H), 0.36 (d, J = 5.2 Hz, 2H).
[0483] Compound 69: 8.18 (d, J = 8.2 Hz, 1H), 7.66 (d, J = 8.2 Hz, 1H), 5.52-5.44 (m, 2H), 3.91 (q, J = 7.3 Hz, 2H), 3.79 (d, J = 14.8 Hz, 1H), 3.32-3.25 (m, 3H), 2.16-2.08 (m, 3H), 1.29 (td, J = 14.8, 7.3 Hz, 3H), 1.00-0.98 (m, 1H), 0.59 (d, J = 4.4 Hz, 2H), 0.37 (d, J = 6.6 Hz, 2H).
[0484] Compound 70: 8.13 (d, J = 8.0 Hz, 1H), 7.67 (d, J = 8.0 Hz, 1H), 7.26 (s, 1H), 5.44 (d, J = 6.0 Hz, 2H), 3.62 (s, 3H), 3.47-3.41 (m, 2H), 2.13 (d, J = 5.5 Hz, 3H), 1.25-1.19 (m, 3H).
[0485] Compound 71: 8.13 (d, J = 8.2 Hz, 1H), 7.67 (d, J = 8.2 Hz, 1H), 7.27 (s, 1H), 5.72 (s, 1H), 5.45 (t, J = 3.4 Hz, 2H), 4.01 (q, J = 7.2 Hz, 2H), 2.14-2.12 (m, 3H), 1.73-1.64 (m, 2H), 1.36 (q, J = 7.3 Hz, 3H), 1.03-0.95 (m, 3H).
[0486] Compound 72: 8.19 (d, J = 8.2 Hz, 1H), 7.52 (d, J = 8.2 Hz, 1H), 5.56 (s, 2H), 3.65 (s, 3H), 3.44 (t, J = 7.4 Hz, 2H), 2.17 (s, 3H), 1.65 (s, 3H), 1.33 (t, J = 7.3 Hz, 3H).
[0487] Compound 73: 8.14 (d, J = 8.2 Hz, 1H), 7.60 (d, J = 8.0 Hz, 1H), 5.45 (d, J = 3.8 Hz, 2H), 3.93 (q, J = 7.2 Hz, 2H), 3.42 (q, J = 7.4 Hz, 2H), 2.16-2.08 (m, 3H), 1.61 (s, 3H), 1.32 (t, J = 7.1 Hz, 3H), 1.24-1.17 (m, 3H).
[0488] Compound 78: 8.18 (d, J = 8.0 Hz, 1H), 7.54 (d, J = 8.0 Hz, 1H), 5.56 (s, 2H), 3.66 (s, 3H), 3.47 (q, J = 7.4 Hz, 2H), 2.18 (s, 3H), 2.14 (s, 1H), 1.34-1.30 (m, 3H), 0.96 (d, J = 6.9 Hz, 6H).
[0489] Compound 82: 8.18 (d, J = 8.2 Hz, 1H), 7.59 (d, J = 8.0 Hz, 1H), 5.55 (s, 2H), 5.31 (s, 0H), 3.61 (s, 3H), 3.45 (d, J = 7.4 Hz, 2H), 2.17 (s, 3H), 1.32 (t, J = 7.4 Hz, 3H), 0.89 (s, 1H), 0.71 (s, 2H), 0.41 (dd, J = 8.2, 2.2 Hz, 2H).
[0490] Compound 83: 8.14 (d, J = 8.2 Hz, 1H), 7.66 (d, J = 8.0 Hz, 1H), 5.45 (t, J = 6.0 Hz, 2H), 3.90 (q, J = 7.3 Hz, 2H), 3.81 (s, 1H), 3.41 (q, J = 7.4 Hz, 2H), 2.15-2.08 (m, 3H), 1.34-1.26 (m, 3H), 1.24-1.16 (m, 3H), 0.97 (t, J = 4.5 Hz, 1H), 0.59 (d, J = 4.7 Hz, 2H), 0.37-0.35 (m, 2H).
[0491] Compound 84: 8.13 (d, J = 8.2 Hz, 1H), 7.67 (d, J = 8.0 Hz, 1H), 7.25 (s, 1H), 5.45 (s, 2H), 3.62 (s, 3H), 3.44-3.40 (m, 2H), 2.14 (s, 3H), 1.71-1.63 (m, 2H), 0.99 (t, J = 7.4 Hz, 3H).
[0492] Compound 85: 8.66-8.38 (m, 1H), 8.18 (d, J = 8.2 Hz, 1H), 7.63 (d, J = 8.2 Hz, 1H), 5.58 (s, 2H), 4.09 (q, J = 7.2 Hz, 2H), 3.47-3.43 (m, 2H), 2.20 (s, 3H), 1.83-1.73 (m, 2H), 1.46 (t, J = 7.1 Hz, 3H), 1.05 (t, J = 7.4 Hz, 3H).
[0493] Compound 86: 8.19 (d, J = 8.0 Hz, 1H), 7.51 (d, J = 8.0 Hz, 1H), 5.56 (s, 2H), 3.64 (s, 3H), 3.41 (t, J = 7.8 Hz, 2H), 2.21-2.13 (m, 3H), 1.79-1.73 (m, 2H), 1.67 (d, J = 15.1 Hz, 3H), 1.04 (t, J = 7.4 Hz, 3H).
[0494] Compound 87: 8.17-8.11 (m, 1H), 7.63-7.57 (m, 1H), 5.48-5.41 (m, 2H), 3.98-3.87 (m, 2H), 3.44-3.35 (m, 2H), 2.14-2.11 (m, 3H), 1.73-1.62 (m, 3H), 1.60 (s, 2H), 1.36-1.28 (m, 3H), 1.01-0.94 (m, 3H).
[0495] Compound 89: 8.21-8.15 (m, 1H), 7.55-7.50 (m, 1H), 5.55 (d, J = 14.8 Hz, 2H), 4.02 (td, J = 14.7, 7.6 Hz, 2H), 3.48-3.40 (m, 2H), 2.17 (d, J = 4.1 Hz, 3H), 2.05-1.89 (m, 2H), 1.75 (d, J = 6.9 Hz, 2H), 1.47-1.40 (m, 3H), 1.08-1.00 (m, 3H), 0.93-0.86 (m, 3H).
[0496] Compound 96: 8.17 (d, J = 8.0 Hz, 1H), 7.57 (d, J = 8.0 Hz, 1H), 5.56 (s, 2H), 3.61 (s, 3H), 3.41 (t, J = 7.7 Hz, 2H), 2.17 (s, 3H), 1.74 (d, J = 7.4 Hz, 2H), 1.03 (t, J = 7.4 Hz, 3H), 0.87-0.85 (m, 1H), 0.71 (s, 2H), 0.41 (dd, J = 8.2, 2.2 Hz, 2H).
[0497] Compound 97: 8.14(dd,J=15.0,6.7Hz,1H),7.66(dd,J=14.8,6.9Hz,1H),5.45(s,2H),3.91(td,J=14.7,7.6Hz,2H),3.41-3.37(m,2H),2 .11(t,J=4.0Hz,3H),1.68-1.58(m,2H),1.34-1.27(m,3H),1.00-0.91(m,4H),0.60(q,J=4.9Hz,2H),0.36(dd,J=8.2,2.2Hz,2H).
[0498] Compound 98: 8.11 (d, J = 8.2 Hz, 1H), 7.67 (d, J = 8.0 Hz, 1H), 7.26 (s, 1H), 5.42 (d, J = 3.6 Hz, 2H), 3.67 (q, J = 6.8 Hz, 1H), 3.62 (s, 3H), 2.13 (s, 3H), 1.28 (d, J = 6.6 Hz, 6H).
[0499] Compound 99: 8.14-8.09 (m, 1H), 7.70-7.64 (m, 1H), 7.29 (q, J = 14.9 Hz, 1H), 5.42 (d, J = 7.1 Hz, 2H), 4.01 (td, J = 14.7, 7.6 Hz, 2H), 3.69-3.62 (m, 1H), 2.13-2.12 (m, 3H), 1.37-1.33 (m, 3H), 1.31-1.27 (m, 6H).
[0500] Compound 100: 8.13 (d, J = 8.0 Hz, 1H), 7.59 (d, J = 8.0 Hz, 1H), 5.45-5.41 (m, 2H), 3.61 (q, J = 6.9 Hz, 1H), 3.54 (s, 3H), 2.13-2.11 (m, 3H), 1.60 (s, 3H), 1.30-1.24 (m, 6H).
[0501] Compound 101: 8.13 (d, J = 8.2 Hz, 1H), 7.60 (d, J = 8.0 Hz, 1H), 5.44 (d, J = 11.0 Hz, 2H), 3.93 (q, J = 7.2 Hz, 2H), 3.62 (t, J = 6.7 Hz, 1H), 2.11 (t, J = 15.0 Hz, 3H), 1.60 (s, 3H),
[0502] 1.34-1.30(m,3H),1.25(dd,J=15.1,6.9Hz,6H).
[0503] Compound 105: 8.19-8.15 (m, 1H), 7.53 (d, J = 8.2 Hz, 1H), 5.53 (t, J = 14.8 Hz, 2H), 4.02 (q, J = 7.3 Hz, 2H), 3.69-3.62 (m, 1H), 2.17 (t, J = 15.0 Hz, 3H), 2.12-2.05 (m, 1H), 1.48-1.29 (m, 9H), 0.95 (td, J = 14.8, 6.9 Hz, 6H).
[0504] Compound 110: 8.11 (d, J = 8.0 Hz, 1H), 7.64 (d, J = 8.0 Hz, 1H), 5.41 (d, J = 4.4 Hz, 2H), 4.06-4.66 (1H), 3.65-3.58 (m, 1H), 3.51 (s, 3H), 2.11 (d, J = 3.0 Hz, 3H), 1.28-1.20 (m, 6H), 0.91 (s, 1H), 0.58 (s, 2H), 0.34 (d, J = 5.8 Hz, 2H).
[0505] Compound 111: 8.16 (dd, J = 15.0, 6.7 Hz, 1H), 7.60-7.56 (m, 1H), 5.52 (t, J = 15.0 Hz, 2H), 4.02-3.95 (m, 2H), 3.67-3.60 (m, 1H), 2.16 (s, 3H), 1.42-1.35 (m, 9H), 0.92-0.86 (m, 1H), 0.71 (s, 2H), 0.40 (dd, J = 8.2, 2.2 Hz, 2H).
[0506] Compound 112: 8.13 (d, J = 8.0 Hz, 1H), 7.67 (d, J = 8.0 Hz, 1H), 7.25 (s, 1H), 5.57-6.04 (1H), 5.45 (d, J = 1.9 Hz, 2H), 3.62 (s, 3H), 3.46-3.42 (m, 2H), 2.13 (s, 3H), 1.66-1.62 (m, 2H), 1.41 (q, J = 7.4 Hz, 2H), 0.90 (t, J = 7.3 Hz, 3H).
[0507] Compound 113: 8.13 (d, J = 8.0 Hz, 1H), 7.68 (d, J = 8.0 Hz, 1H), 7.27 (s, 1H), 5.46 (s, 2H), 4.01 (td, J = 14.8, 7.5 Hz, 2H), 3.46-3.40 (m, 2H), 2.13-2.11 (m, 3H), 1.70-1.58 (m, 2H),
[0508] 1.46-1.38(m,2H),1.36(t,J=7.3Hz,3H),0.91(q,J=7.5Hz,3H).
[0509] Compound 114: 8.19 (d, J = 8.0 Hz, 1H), 7.51 (d, J = 8.0 Hz, 1H), 5.57 (s, 2H), 3.64 (t, J = 15.0 Hz, 3H), 3.42 (t, J = 8.0 Hz, 2H), 2.16 (t, J = 15.1 Hz, 3H), 1.71 (t, J = 7.3 Hz, 2H), 1.63 (d, J = 14.8 Hz, 3H), 1.43 (q, J = 7.5 Hz, 2H), 0.93 (t, J = 7.4 Hz, 3H).
[0510] Compound 115: 8.14 (dd, J = 15.0, 7.0 Hz, 1H), 7.60 (dd, J = 14.8, 6.9 Hz, 1H), 5.45 (t, J = 14.8 Hz, 2H), 3.93 (qd, J = 14.8, 7.2 Hz, 2H), 3.47-3.35 (m, 2H), 2.11 (t, J = 4.1 Hz, 3H), 1.69-1.56 (m, 5H), 1.43-1.36 (m, 2H), 1.34-1.27 (m, 3H), 0.92-0.84 (m, 3H).
[0511] Compound 124: 8.17 (t, J = 4.1 Hz, 1H), 7.58-7.56 (m, 1H), 5.56 (s, 2H), 3.61 (s, 3H), 3.43 (t, J = 8.0 Hz, 2H), 2.16 (d, J = 4.4 Hz, 3H), 1.73-1.65 (m, 2H), 1.43 (td, J = 15.0, 7.5 Hz, 2H), 0.92 (t, J = 7.3 Hz, 3H), 0.89-0.82 (m, 1H), 0.78-0.72 (m, 2H), 0.41 (dd, J = 8.2, 2.2 Hz, 2H).
[0512] Compound 125: 8.14 (d, J = 8.2 Hz, 1H), 7.66 (d, J = 8.2 Hz, 1H), 5.45 (s, 2H), 3.91 (q, J = 7.3 Hz, 2H), 3.41 (t, J = 8.0 Hz, 2H), 2.11 (s, 3H), 1.60-1.54 (m, 2H), 1.43-1.35 (m, 2H), 1.33-1.28 (m, 3H), 0.88 (td, J = 14.9, 7.4 Hz, 4H), 0.60 (s, 2H), 0.34 (d, J = 6.0 Hz, 2H).
[0513] Compound 126: 8.09 (t, J = 4.1 Hz, 1H), 7.67 (d, J = 8.0 Hz, 1H), 7.27 (s, 1H), 5.44 (s, 2H), 3.62 (s, 3H), 2.13 (d, J = 3.6 Hz, 3H), 1.34 (s, 9H).
[0514] Compound 127: 8.11-8.07 (m, 1H), 7.69-7.64 (m, 1H), 7.31-7.26 (m, 1H), 5.44-5.41 (m, 2H), 4.05-3.97 (m, 2H), 2.15-2.11 (m, 3H), 1.38-1.32 (m, 12H).
[0515] Compound 128: 8.09 (d, J = 8.2 Hz, 1H), 7.57 (d, J = 8.0 Hz, 1H), 5.49 (d, J = 1.4 Hz, 2H), 3.45 (s, 3H), 2.16 (s, 3H), 2.11 (d, J = 2.5 Hz, 2H), 1.37 (s, 9H).
[0516] Compound 129: 8.09 (d, J = 8.2 Hz, 1H), 7.58 (d, J = 8.2 Hz, 1H), 5.49 (s, 2H), 3.88 (q, J = 7.2 Hz, 2H), 2.16 (t, J = 3.6 Hz, 3H), 2.12 (s, 3H), 1.37-1.34 (m, 9H), 1.30 (t, J = 7.1 Hz, 3H).
[0517] Compound 138: 8.12-8.10 (m, 1H), 7.57 (d, J = 8.2 Hz, 1H), 5.63-5.34 (m, 2H), 3.61 (s, 3H), 2.13 (t, J = 4.1 Hz, 3H), 1.38 (s, 9H), 0.97-0.90 (m, 1H), 0.67 (s, 2H), 0.41-0.34 (m, 2H).
[0518] Compound 139: 8.15-8.04 (m, 1H), 7.65 (d, J = 8.2 Hz, 1H), 5.49 (t, J = 15.0 Hz, 2H),
[0519] 3.95-3.84(m,2H),2.19-2.10(m,3H),1.74-1.59(m,1H),1.37(s,9H),1.28(t,J=7.1Hz,3H),0.83-0.72(m,2H),0.57(d,J=53.0Hz,2H).
[0520] Compound 141: 8.07 (d, J = 8.0 Hz, 1H), 7.43 (d, J = 8.0 Hz, 1H), 5.50 (s, 2H), 3.52 (s, 3H), 3.29 (s, 3H), 3.04-3.00 (m, 2H), 2.77 (t, J = 7.6 Hz, 2H), 2.21 (s, 3H), 2.11 (d, J = 2.7 Hz, 3H), 1.43 (td, J = 14.7, 7.2 Hz, 4H), 0.83-0.78 (m, 6H).
[0521] Compound 142: 8.02 (d, J = 8.2 Hz, 1H), 7.42 (d, J = 8.0 Hz, 1H), 5.46 (s, 2H), 3.52 (s, 3H), 3.41 (q, J = 7.4 Hz, 2H), 3.04-3.00 (m, 2H), 2.77 (t, J = 7.7 Hz, 2H), 2.20 (s, 3H), 2.09 (s, 3H), 1.44 (td, J = 14.6, 7.4 Hz, 4H), 1.27-1.24 (m, 3H), 0.84-0.78 (m, 6H).
[0522] Compound 143: 8.03-7.98 (m, 1H), 7.44-7.38 (m, 1H), 5.46-5.39 (m, 2H), 3.67-3.60 (m, 1H), 3.53 (d, J = 8.5 Hz, 3H), 3.04-2.99 (m, 2H), 2.78 (q, J = 7.4 Hz, 2H), 2.25-2.17 (m, 3H),
[0523] 2.11-2.08(m,3H),1.44(qd,J=15.1,7.6Hz,4H),1.33-1.27(m,6H),0.82(qd,J=7.5,3.9Hz,6H).
[0524] Compound 144: 8.07 (d, J = 8.0 Hz, 1H), 7.47 (d, J = 8.2 Hz, 1H), 5.50 (s, 2H), 3.50 (s, 3H), 3.28 (s, 3H), 3.05 (t, J = 7.7 Hz, 2H), 2.85 (t, J = 7.6 Hz, 2H), 2.10 (s, 3H), 1.94-1.89 (m, 1H), 1.50-1.42 (m, 4H), 0.86-0.78 (m, 10H).
[0525] Compound 149: 8.09 (d, J = 8.0 Hz, 1H), 7.47 (d, J = 8.0 Hz, 1H), 5.57-5.53 (m, 2H), 3.56 (s, 3H), 3.33 (s, 3H), 3.24-3.17 (m, 2H), 3.06-2.95 (m, 2H), 2.34-2.29 (m, 3H), 2.14 (s, 3H),
[0526] 1.64-1.49(m,8H).
[0527] Compound 150: 8.01 (t, J = 4.1 Hz, 1H), 7.42 (d, J = 8.0 Hz, 1H), 5.46 (t, J = 14.4 Hz, 2H), 3.53 (s, 3H), 3.44-3.39 (m, 2H), 3.20 (t, J = 5.9 Hz, 2H), 3.02-2.92 (m, 2H), 2.29 (s, 3H), 2.11 (d, J = 7.4 Hz, 3H), 1.66-1.46 (m, 8H), 1.26 (t, J = 7.4 Hz, 3H).
[0528] Compound 151: 7.99 (t, J = 4.0 Hz, 1H), 7.41 (d, J = 8.0 Hz, 1H), 5.43 (t, J = 14.8 Hz, 2H), 3.67-3.60 (m, 1H), 3.52 (s, 3H), 3.27-3.19 (m, 2H), 2.97 (t, J = 5.4 Hz, 2H), 2.29 (s, 3H), 2.08 (d, J = 4.1 Hz, 3H), 1.61-1.46 (m, 8H), 1.30 (d, J = 6.6 Hz, 6H).
[0529] Compound 152: 8.06 (d, J = 8.2 Hz, 1H), 7.47 (d, J = 8.2 Hz, 1H), 5.51 (s, 2H), 3.49 (s, 3H), 3.45-3.33 (m, 1H), 3.29 (s, 3H), 3.26-3.21 (m, 2H), 3.02 (t, J = 5.6 Hz, 2H), 2.11 (s, 3H),
[0530] 1.65-1.47(m,8H),0.87-0.83(m,2H),0.76-0.71(m,2H).
[0531] Compound 153: 8.01 (d, J = 8.0 Hz, 1H), 7.46 (d, J = 8.2 Hz, 1H), 5.46 (s, 2H), 3.49 (s, 3H), 3.41 (q, J = 7.4 Hz, 2H), 3.23 (t, J = 5.9 Hz, 2H), 3.03 (t, J = 5.6 Hz, 2H), 2.09 (s, 4H), 1.61-1.44 (m, 8H), 1.26 (t, J = 7.4 Hz, 3H), 0.87-0.83 (m, 2H), 0.76-0.71 (m, 2H).
[0532] Compound 154: 7.93 (td, J = 15.0, 8.2 Hz, 1H), 7.47-7.33 (m, 2H), 5.55-5.31 (m, 2H),
[0533] 3.86-3.79(m,3H),3.63-3.54(m,3H),3.28-3.18(m,3H),2.49-2.41(m,3H),2.39-2.28(m,3H),2.19-2.10(m,3H).
[0534] Compound 155: 7.90 (d, J = 8.2 Hz, 1H), 7.44 (s, 1H), 7.40 (d, J = 8.2 Hz, 1H), 5.34 (s, 2H), 3.86 (s, 3H), 3.61 (s, 3H), 3.36 (q, J = 7.3 Hz, 2H), 2.47 (s, 3H), 2.39 (s, 3H), 2.16 (s, 3H), 1.26 (t, J = 7.4 Hz, 3H).
[0535] Compound 156: 7.90-7.79 (m, 1H), 7.42-7.29 (m, 2H), 5.53-5.27 (m, 2H), 3.89-3.74 (m, 3H), 3.63-3.51 (m, 3H), 3.43-3.23 (m, 2H), 2.50-2.40 (m, 3H), 2.38-2.25 (m, 3H), 2.16-2.08 (m, 3H), 1.72-1.57 (m, 2H), 1.03-0.90 (m, 3H).
[0536] Compound 157: 7.87 (dd, J = 15.1, 6.9 Hz, 1H), 7.43 (s, 1H), 7.41-7.36 (m, 1H), 5.34-5.31 (m, 2H), 3.87 (s, 3H), 3.60 (s, 3H), 3.58-3.49 (m, 1H), 2.47 (s, 3H), 2.39 (s, 3H), 2.15 (t, J = 4.2 Hz, 3H), 1.34-1.25 (m, 6H).
[0537] Compound 158: 7.99 (d, J = 8.2 Hz, 1H), 7.74 (s, 1H), 7.63 (s, 1H), 7.43 (d, J = 8.2 Hz, 1H), 5.38 (s, 2H), 3.82 (s, 3H), 3.66 (s, 3H), 3.22 (s, 3H), 2.36 (s, 3H), 2.11 (s, 3H).
[0538] Compound 159: 7.99 (d, J = 8.2 Hz, 1H), 7.82 (s, 1H), 7.67 (s, 1H), 7.49 (d, J = 8.2 Hz, 1H), 5.41 (s, 2H), 3.89 (s, 3H), 3.72 (s, 3H), 3.40 (q, J = 7.4 Hz, 2H), 2.43 (d, J = 6.6 Hz, 3H),
[0539] 2.17-2.15(m,3H),1.29(t,J=7.4Hz,3H).
[0540] Compound 160: 7.99 (d, J = 8.2 Hz, 1H), 7.83 (s, 1H), 7.66 (s, 1H), 7.48 (d, J = 8.0 Hz, 1H), 5.41 (s, 2H), 3.89 (s, 3H), 3.72 (s, 3H), 3.38-3.34 (m, 2H), 2.44 (s, 3H), 2.17 (d, J = 4.4 Hz, 3H), 1.71 (q, J = 7.8 Hz, 2H), 1.01 (t, J = 7.4 Hz, 3H).
[0541] Compound 161: 7.98-7.87 (m, 1H), 7.83-7.77 (m, 1H), 7.63-7.59 (m, 1H), 7.49-7.41 (m, 1H), 5.40-5.31 (m, 2H), 3.88-3.84 (m, 3H), 3.69 (t, J = 15.0 Hz, 3H), 3.60-3.55 (m, 1H), 2.43-2.36 (m, 3H), 2.16-2.11 (m, 3H), 1.32-1.26 (m, 6H).
[0542] Compound 162: 7.97 (dd, J = 15.1, 6.9 Hz, 1H), 7.47 (d, J = 4.3 Hz, 1H), 7.46-7.43 (m, 1H), 5.46-5.34 (m, 2H), 3.86 (d, J = 5.2 Hz, 3H), 3.56 (s, 3H), 3.25 (d, J = 4.7 Hz, 3H), 2.47-2.40 (m, 1H), 2.38 (s, 3H), 2.16 (d, J = 4.4 Hz, 3H), 1.03-0.97 (m, 2H), 0.95-0.89 (m, 2H).
[0543] Compound 163: 7.88 (d, J = 8.2 Hz, 1H), 7.67 (s, 1H), 7.48 (d, J = 8.2 Hz, 1H), 5.30 (s, 2H), 3.77 (s, 3H), 3.49 (s, 3H), 3.31 (d, J = 7.4 Hz, 2H), 2.42-2.50 (1H), 2.27 (s, 3H), 2.13 (d, J = 1.9 Hz, 3H), 1.14 (t, J = 7.3 Hz, 3H), 0.93-0.90 (m, 4H).
[0544] Compound 164: 7.88 (d, J = 8.0 Hz, 1H), 7.67 (s, 1H), 7.48 (d, J = 8.2 Hz, 1H), 5.32 (d, J = 14.8 Hz, 2H), 3.77 (s, 3H), 3.49 (d, J = 4.1 Hz, 3H), 3.31-3.27 (m, 2H), 2.49-2.42 (m, 1H), 2.28 (d, J = 5.2 Hz, 3H), 2.12 (d, J = 4.4 Hz, 3H), 1.63-1.53 (m, 2H), 0.97-0.92 (m, 4H), 0.91 (t, J = 2.3 Hz, 3H).
[0545] Compound 165: 7.93-7.77 (m, 1H), 7.50-7.42 (m, 1H), 7.38 (dd, J=15.0, 8.1 Hz, 1H), 5.39-5.28 (m, 2H), 3.88-3.80 (m, 3H), 3.60-3.49 (m, 4H), 2.46-2.33 (m, 4H), 2.16-2.09 (m, 3H), 1.33-1.22 (m, 6H), 1.02-0.94 (m, 2H), 0.93-0.82 (m, 2H).
[0546] Compound 166: 7.84 (d, J = 8.0 Hz, 1H), 7.71 (s, 1H), 7.37-7.33 (m, 1H), 5.34 (s, 2H), 3.92 (s, 3H), 3.54 (s, 3H), 3.18 (s, 3H), 2.39 (d, J = 7.6 Hz, 3H), 2.11-2.08 (m, 3H).
[0547] Compound 167: 7.78 (d, J = 8.2 Hz, 1H), 7.69 (s, 1H), 7.33 (d, J = 8.0 Hz, 1H), 5.31 (t, J = 13.9 Hz, 2H), 3.93 (s, 3H), 3.54 (s, 3H), 3.29 (q, J = 7.3 Hz, 2H), 2.40 (s, 3H), 2.10 (d, J = 2.7 Hz, 3H), 1.19 (t, J = 7.4 Hz, 3H).
[0548] Compound 168: 7.78 (t, J = 4.0 Hz, 1H), 7.67 (s, 1H), 7.32 (d, J = 8.2 Hz, 1H), 5.31 (t, J = 14.0 Hz, 2H), 3.92 (s, 3H), 3.54 (s, 3H), 3.25 (t, J = 8.0 Hz, 2H), 2.40 (s, 3H), 1.73-1.53 (m, 3H), 1.31-1.16 (m, 2H), 0.93 (t, J = 7.4 Hz, 3H).
[0549] Compound 169: 7.75 (d, J = 8.0 Hz, 1H), 7.71 (d, J = 7.4 Hz, 1H), 7.32 (dd, J = 15.1, 6.9 Hz, 1H), 5.35-5.28 (m, 2H), 3.94 (d, J = 8.5 Hz, 3H), 3.54 (s, 3H), 3.51-3.44 (m, 1H), 2.40 (s, 3H), 2.09 (s, 3H), 1.23 (d, J = 6.3 Hz, 6H).
[0550] Compound 170: 8.02 (d, J = 8.2 Hz, 1H), 7.96 (s, 1H), 7.79 (s, 1H), 7.49 (d, J = 8.2 Hz, 1H), 5.47 (s, 2H), 4.01 (s, 3H), 3.73 (d, J = 4.1 Hz, 3H), 3.28 (d, J = 2.7 Hz, 3H), 2.17 (d, J = 2.5 Hz, 3H).
[0551] Compound 171: 7.96 (s, 1H), 7.83 (s, 1H), 7.49 (d, J = 8.0 Hz, 1H), 5.44 (s, 2H), 4.14 (d, J = 1.9 Hz, 1H), 4.03 (s, 2H), 4.02 (s, 3H), 3.73 (s, 3H), 3.40 (q, J = 7.4 Hz, 2H), 2.17 (s, 3H), 1.29 (t, J = 7.4 Hz, 3H).
[0552] Compound 172: 7.90-7.87 (m, 2H), 7.76 (s, 1H), 7.40 (d, J = 8.2 Hz, 1H), 5.37 (s, 2H), 3.95 (s, 3H), 3.66 (s, 3H), 3.30-3.26 (m, 2H), 2.09 (d, J = 3.6 Hz, 3H), 1.67-1.62 (m, 2H), 0.96-0.92 (m, 3H).
[0553] Compound 173: 7.87-7.84 (m, 2H), 7.78 (s, 1H), 7.40-7.38 (m, 1H), 5.33 (s, 2H), 3.95 (s, 3H), 3.66 (s, 3H), 3.55-3.47 (m, 1H), 2.09 (s, 3H), 1.27-1.24 (m, 6H).
[0554] Compound 174: 7.94-7.90 (m, 1H), 7.79 (s, 1H), 7.46-7.43 (m, 1H), 5.43 (s, 2H), 3.99 (s, 3H), 3.57 (s, 3H), 3.26 (s, 3H), 2.35 (dd, J=21.3, 4.8 Hz, 1H), 2.17 (s, 3H), 1.00-0.96 (m, 2H), 0.95-0.87 (m, 2H).
[0555] Compound 175: 7.84 (dd, J = 8.1, 3.2 Hz, 1H), 7.76 (s, 1H), 7.41 (d, J = 8.2 Hz, 1H), 5.36 (s, 2H), 3.97 (d, J = 4.7 Hz, 3H), 3.54 (s, 3H), 3.34 (q, J = 7.4 Hz, 2H), 2.47-2.29 (m, 1H), 2.14 (d, J = 2.7 Hz, 3H), 1.24 (t, J = 7.3 Hz, 3H), 1.00-0.94 (m, 2H), 0.93-0.87 (m, 2H).
[0556] Compound 176: 7.98 (s, 1H), 7.87 (d, J = 8.0 Hz, 1H), 7.49 (d, J = 8.0 Hz, 1H), 5.32 (s, 2H), 3.93 (s, 3H), 3.53 (d, J = 15.1 Hz, 3H), 3.31 (t, J = 8.0 Hz, 2H), 2.41 (t, J = 6.5 Hz, 1H), 2.12 (s, 3H), 1.59 (q, J = 7.7 Hz, 2H), 0.95 (t, J = 7.4 Hz, 3H), 0.90 (d, J = 6.3 Hz, 4H).
[0557] Compound 177: 7.82 (dd, J = 15.0, 8.1 Hz, 1H), 7.74 (dd, J = 22.3, 7.1 Hz, 1H), 7.44-7.34 (m, 1H), 5.38-5.29 (m, 2H), 4.04-3.89 (m, 3H), 3.60-3.44 (m, 4H), 2.38 (s, 1H), 2.19-2.07 (m, 3H), 1.26 (dd, J = 21.8, 15.0 Hz, 6H), 1.01-0.92 (m, 2H), 0.91-0.84 (m, 2H).
[0558] Compound 178: 7.90-7.79 (m, 1H), 7.58-7.50 (m, 1H), 7.39-7.28 (m, 1H), 5.60-5.28 (m, 2H), 4.16-4.04 (m, 2H), 3.59 (t, J = 15.0 Hz, 3H), 3.28-3.13 (m, 3H), 2.53-2.45 (m, 3H), 2.41-2.33 (m, 3H), 2.17-2.10 (m, 3H), 1.43-1.36 (m, 3H).
[0559] Compound 179: 7.76 (d, J = 8.0 Hz, 1H), 7.54 (s, 1H), 7.28 (d, J = 8.2 Hz, 1H), 5.24 (d, J = 7.4 Hz, 2H), 4.05 (q, J = 7.3 Hz, 2H), 3.54 (d, J = 4.1 Hz, 3H), 3.25 (t, J = 8.0 Hz, 2H), 2.44 (s, 3H), 2.32 (s, 3H), 2.07 (s, 3H), 1.61-1.55 (m, 2H), 1.35 (t, J = 7.3 Hz, 3H), 0.91 (t, J = 7.4 Hz, 3H).
[0560] Compound 180: 7.90 (d, J = 8.2 Hz, 1H), 7.84 (s, 1H), 7.66 (s, 1H), 7.37 (d, J = 8.2 Hz, 1H), 5.36 (s, 2H), 4.07 (q, J = 7.3 Hz, 2H), 3.65 (s, 3H), 3.19 (s, 3H), 2.38 (s, 3H), 2.09 (s, 3H), 1.37 (t, J = 7.3 Hz, 3H).
[0561] Compound 181: 7.94-7.91 (m, 2H), 7.76 (s, 1H), 7.43 (d, J = 8.2 Hz, 1H), 5.38 (s, 2H), 4.14 (q, J = 7.3 Hz, 2H), 3.73 (d, J = 4.1 Hz, 3H), 3.37-3.33 (m, 2H), 2.45 (s, 3H), 2.16 (d, J = 4.7 Hz, 3H), 1.73-1.63 (m, 2H), 1.44 (t, J = 7.3 Hz, 3H), 1.00 (t, J = 7.4 Hz, 3H).
[0562] Compound 182: 7.82 (d, J = 8.2 Hz, 1H), 7.51 (s, 1H), 7.32 (d, J = 8.2 Hz, 1H), 5.32 (s, 2H), 4.05 (q, J = 7.3 Hz, 2H), 3.49 (s, 3H), 3.16 (s, 3H), 2.49-2.44 (m, 1H), 2.34 (s, 3H), 2.09 (d, J = 3.8 Hz, 3H), 1.36 (q, J = 7.5 Hz, 3H), 0.96-0.92 (m, 2H), 0.91-0.87 (m, 2H).
[0563] Compound 183: 7.77 (d, J = 8.0 Hz, 1H), 7.55 (s, 1H), 7.31 (d, J = 8.0 Hz, 1H), 5.27 (d, J = 1.6 Hz, 2H), 4.05 (q, J = 7.3 Hz, 2H), 3.50 (s, 3H), 3.25 (t, J = 8.0 Hz, 2H), 2.46-2.42 (m, 1H), 2.33 (s, 3H), 2.07 (t, J = 4.0 Hz, 3H), 1.61-1.56 (m, 2H), 1.35 (t, J = 7.3 Hz, 3H), 0.97-0.86 (m, 7H).
[0564] Compound 184: 7.79 (dd, J = 14.8, 6.9 Hz, 1H), 7.69 (t, J = 15.0 Hz, 1H), 7.33-7.27 (m, 1H), 5.45-5.27 (m, 2H), 4.41-4.31 (m, 2H), 3.56 (s, 3H), 3.29 (td, J = 14.9, 7.5 Hz, 2H), 2.37 (t, J = 15.0 Hz, 3H), 2.11-2.07 (m, 3H), 1.44 (q, J = 7.4 Hz, 3H), 1.17 (t, J = 7.3 Hz, 3H).
[0565] Compound 185: 7.78 (d, J = 8.0 Hz, 1H), 7.72 (s, 1H), 7.29 (d, J = 8.0 Hz, 1H), 5.28 (s, 2H), 4.37 (q, J = 7.2 Hz, 2H), 3.56 (s, 3H), 3.54-3.49 (m, 1H), 2.35 (s, 3H), 2.07 (s, 3H), 1.43 (t, J = 7.3 Hz, 3H), 1.20 (d, J = 6.9 Hz, 6H).
[0566] Compound 186: 7.96-7.86 (m, 2H), 7.75-7.65 (m, 1H), 7.46-7.36 (m, 1H), 5.38 (t, J = 15.0 Hz, 2H), 4.44-4.32 (m, 2H), 3.72-3.65 (m, 3H), 3.38-3.29 (m, 2H), 2.13-2.02 (m, 3H), 1.49-1.41 (m, 3H), 1.24-1.17 (m, 3H).
[0567] Compound 187: 7.90 (d, J = 8.0 Hz, 2H), 7.69 (s, 1H), 7.42-7.39 (m, 1H), 5.35 (s, 2H), 4.38 (td, J = 7.5, 6.8 Hz, 2H), 3.68 (s, 3H), 3.58-3.50 (m, 1H), 2.08 (s, 3H), 1.45 (t, J = 7.3 Hz, 3H), 1.24 (d, J = 6.6 Hz, 6H).
[0568] Compound 188: 7.88 (d, J = 8.0 Hz, 1H), 7.79 (s, 1H), 7.42 (d, J = 8.2 Hz, 1H), 5.41 (s, 2H), 4.43 (q, J = 7.2 Hz, 2H), 3.59 (s, 3H), 3.37 (q, J = 7.3 Hz, 2H), 2.32-2.30 (m, 1H), 2.15 (s, 3H), 1.51 (t, J = 7.3 Hz, 3H), 1.25 (t, J = 7.3 Hz, 3H), 1.00-0.96 (m, 2H), 0.93-0.87 (m, 2H).
[0569] Compound 189: 7.80(d,J=8.0Hz,1H),7.75(s,1H),7.34(d,J=8.2Hz,1H),5.30(s,2H),4.37(td,J=7.5,6.9Hz,2H),3.55(d,J=6.6Hz,1H),3.52(d, J=4.9Hz,3H),2.22(t,J=4.8Hz,1H),2.07(t,J=4.7Hz,3H),1.43(t,J=7.3Hz,3H),1.24-1.16(m,6H),0.92-0.85(m,2H),0.85-0.78(m,2H).
[0570] Compound 190: 7.82 (d, J = 8.2 Hz, 1H), 7.35-7.33 (m, 2H), 5.38-5.27 (m, 2H), 3.83-3.76 (m, 5H), 3.31-3.19 (m, 3H), 2.39 (s, 3H), 2.09 (s, 3H), 1.32 (t, J = 7.3 Hz, 3H), 1.22-1.16 (m, 9H).
[0571] Compound 191: 7.99 (d, J = 8.2 Hz, 1H), 7.71 (s, 1H), 7.64 (s, 1H), 7.45 (d, J = 8.0 Hz, 1H), 5.40 (s, 2H), 3.95 (q, J = 7.3 Hz, 2H), 3.82 (s, 3H), 3.35-3.28 (m, 1H), 3.22 (s, 3H), 2.10 (s, 3H), 1.38 (t, J = 7.3 Hz, 3H), 1.23 (d, J = 7.1 Hz, 6H).
[0572] Compound 192: 7.77 (d, J = 8.2 Hz, 1H), 7.56 (s, 1H), 7.33 (d, J = 8.0 Hz, 1H), 5.29 (s, 2H), 4.06 (q, J = 7.3 Hz, 2H), 3.80 (q, J = 7.2 Hz, 2H), 3.25 (t, J = 8.0 Hz, 2H), 2.73 (q, J = 7.5 Hz, 2H) z,2H),2.39(s,1H),2.07(d,J=4.1Hz,3H),1.63-1.53(m,2H),1.39(t,J=7.3Hz,3H ), 1.29 (t, J = 7.3Hz, 3H), 1.13-1.06 (m, 3H), 0.96-0.91 (m, 4H), 0.89-0.83 (m, 3H).
[0573] Compound 193: 7.84-7.79 (m, 1H), 7.67-7.59 (m, 1H), 7.41-7.34 (m, 1H), 5.34-5.30 (m, 2H), 4.10 (td, J = 14.8, 7.5 Hz, 2H), 3.87-3.82 (m, 2H), 3.63-3.53 (m, 1H), 2.78 (td, J = 15.0, 7. 4Hz,2H),2.46-2.32(m,1H),2.13-2.10(m,3H),1.44(t,J=7.3Hz,3H),1.33(t,J=7.3H z, 3H), 1.26-1.20 (m, 6H), 1.14 (t, J = 7.6Hz, 3H), 1.01-0.95 (m, 2H), 0.91-0.85 (m, 2H).
[0574] Compound 194: 7.84 (dd, J = 14.8, 6.9 Hz, 1H), 7.35-7.30 (m, 1H), 5.58-5.27 (m, 2H), 3.78-3.70 (m, 3H), 3.59-3.51 (m, 3H), 3.19 (t, J = 15.0 Hz, 3H), 2.47-2.40 (m, 3H), 2.31-2.24 (m, 3H), 2.12-2.05 (m, 3H).
[0575] Compound 195: 7.87 (d, J = 8.2 Hz, 1H), 7.39 (d, J = 8.2 Hz, 1H), 5.37 (s, 2H), 3.83 (s, 3H), 3.62 (s, 3H), 3.41-3.36 (m, 2H), 2.52 (d, J = 3.0 Hz, 3H), 2.35 (d, J = 10.2 Hz, 3H), 2.14 (s, 3H), 1.25 (t, J = 7.4 Hz, 3H).
[0576] Compound 196: 7.79 (dd, J=14.8, 6.9 Hz, 1H), 7.33-7.28 (m, 1H), 5.45-5.27 (m, 2H), 3.79-3.71 (m, 3H), 3.59-3.51 (m, 3H), 3.29-3.21 (m, 2H), 2.48-2.40 (m, 3H), 2.32-2.25 (m, 3H), 2.11-2.03 (m, 3H), 1.66-1.53 (m, 2H), 0.95-0.88 (m, 3H).
[0577] Compound 197: 7.78 (d, J = 8.2 Hz, 1H), 7.30 (d, J = 8.2 Hz, 1H), 5.27 (s, 2H), 3.76 (s, 3H), 3.57-3.52 (m, 4H), 2.43 (s, 3H), 2.29 (s, 3H), 2.06 (s, 3H), 1.26-1.21 (m, 6H).
[0578] Compound 198: 7.94 (d, J = 8.2 Hz, 1H), 7.81 (s, 1H), 7.41 (d, J = 8.0 Hz, 1H), 5.39 (s, 2H), 3.77 (s, 3H), 3.66 (s, 3H), 3.22 (s, 3H), 2.33 (s, 3H), 2.09 (s, 3H).
[0579] Compound 199: 7.88 (d, J = 8.0 Hz, 1H), 7.83 (s, 1H), 7.39 (d, J = 8.0 Hz, 1H), 5.35 (s, 2H), 3.77 (s, 3H), 3.66 (s, 3H), 3.33 (q, J = 7.3 Hz, 2H), 2.34 (s, 3H), 2.08 (s, 3H), 1.20 (t, J = 7.4 Hz, 3H).
[0580] Compound 200: 7.87 (d, J = 8.2 Hz, 1H), 7.83 (s, 1H), 7.37 (d, J = 8.2 Hz, 1H), 5.31 (s, 2H), 3.77 (s, 3H), 3.66 (s, 3H), 3.60-3.53 (m, 1H), 2.34 (s, 3H), 2.07 (s, 3H), 1.23 (d, J = 6.9 Hz, 6H).
[0581] Compound 201: 7.93 (d, J = 8.0 Hz, 1H), 7.44 (d, J = 8.2 Hz, 1H), 5.42 (s, 2H), 3.82 (s, 3H), 3.57 (d, J = 2.2 Hz, 3H), 3.26 (s, 3H), 2.47 (d, J = 9.6 Hz, 1H), 2.35 (s, 3H), 2.16 (s, 3H),
[0582] 1.01-0.99(m,2H),0.96(td,J=5.4,2.7Hz,2H).
[0583] Compound 202: 7.88-7.82 (m, 1H), 7.42-7.36 (m, 1H), 5.53-5.31 (m, 2H), 3.80 (s, 3H), 3.56 (d, J = 8.7 Hz, 3H), 3.36 (td, J = 14.9, 7.5 Hz, 2H), 2.53-2.41 (m, 1H), 2.33 (s, 3H), 2.14-2.11 (m, 3H), 1.22 (td, J = 7.2, 3.1 Hz, 3H), 1.02-0.96 (m, 2H), 0.95-0.86 (m, 2H).
[0584] Compound 203: 7.79 (d, J = 8.2 Hz, 1H), 7.34 (d, J = 8.0 Hz, 1H), 5.28 (s, 2H), 3.76 (s, 3H), 3.55 (t, J = 7.3 Hz, 1H), 3.50 (s, 3H), 2.43-2.39 (m, 1H), 2.29 (s, 3H), 2.06 (s, 3H), 1.22 (dd, J = 14.8, 8.0 Hz, 6H), 0.94-0.90 (m, 2H), 0.89-0.85 (m, 2H).
[0585] Compound 204: 7.83-7.81 (m, 1H), 7.33 (d, J = 8.2 Hz, 1H), 5.37 (s, 2H), 3.89 (s, 3H), 3.55 (s, 3H), 3.20 (s, 3H), 2.45 (s, 3H), 2.09 (d, J = 7.7 Hz, 3H).
[0586] Compound 205: 7.76 (d, J = 8.2 Hz, 1H), 7.31 (d, J = 8.2 Hz, 1H), 5.40-5.27 (m, 2H), 3.89 (s, 3H), 3.54 (s, 3H), 3.28 (t, J = 8.0 Hz, 2H), 2.45 (s, 3H), 2.06 (d, J = 4.4 Hz, 3H), 1.67-1.59 (m, 2H), 0.92 (t, J = 7.4 Hz, 3H).
[0587] Compound 206: 7.76 (t, J = 4.0 Hz, 1H), 7.30 (d, J = 8.0 Hz, 1H), 5.29 (s, 2H), 3.90 (s, 3H), 3.58-3.54 (m, 4H), 2.45 (s, 3H), 2.06 (s, 3H), 1.27-1.18 (m, 6H).
[0588] Compound 207: 7.92 (d, J = 8.2 Hz, 1H), 7.83 (s, 1H), 7.40 (d, J = 8.0 Hz, 1H), 5.42 (s, 2H), 3.90 (s, 3H), 3.66 (s, 3H), 3.22 (s, 3H), 2.09 (s, 3H).
[0589] Compound 208: 7.92-7.89 (m, 2H), 7.44 (d, J = 8.2 Hz, 1H), 5.42 (s, 2H), 3.96 (s, 3H), 3.71 (s, 3H), 3.39 (q, J = 7.3 Hz, 2H), 2.13 (s, 3H), 1.25 (t, J = 7.3 Hz, 3H).
[0590] Compound 209: 7.86 (d, J = 8.2 Hz, 2H), 7.38 (d, J = 8.2 Hz, 1H), 5.37 (s, 2H), 3.91 (s, 3H), 3.66 (s, 3H), 3.31 (t, J = 8.0 Hz, 2H), 2.08 (s, 3H), 1.66-1.59 (m, 2H), 0.93 (t, J = 7.4 Hz, 3H).
[0591] Compound 210: 7.83-7.89 (2H), 7.36-7.40 (1H), 5.30-5.36 (2H), 3.90-3.93 (3H), 3.64-3.67 (3H), 3.53-3.61 (1H), 2.05-2.09 (3H), 1.21-1.26 (6H).
[0592] Compound 211: 7.78 (d, J = 8.2 Hz, 1H), 7.35 (d, J = 8.2 Hz, 1H), 5.34 (s, 2H), 3.89 (s, 3H), 3.50 (s, 3H), 3.33 (q, J = 7.4 Hz, 2H), 2.46 (t, J = 4.9 Hz, 1H), 2.07 (s, 3H), 1.21-1.16 (m, 3H), 0.96-0.87 (m, 4H).
[0593] Compound 212: 7.84 (dd, J = 8.1, 3.2 Hz, 1H), 7.44-7.38 (m, 1H), 5.51-5.19 (m, 2H), 3.97 (s, 3H), 3.67-3.61 (m, 1H), 3.58 (d, J = 7.4 Hz, 3H), 2.57-2.46 (m, 1H), 2.13 (d, J = 4.4 Hz, 3H), 1.32 (dd, J = 16.8, 6.6 Hz, 6H), 1.02-0.96 (m, 4H).
[0594] Compound 213: 7.84 (s, 1H), 7.51 (d, J = 8.2 Hz, 1H), 5.26 (d, J = 21.4 Hz, 2H), 3.71 (s, 3H), 3.54 (d, J = 7.4 Hz, 3H), 3.25 (s, 3H), 2.19 (d, J = 7.7 Hz, 3H), 2.02 (s, 3H).
[0595] Compound 214: 7.90-7.79 (m, 1H), 7.36 (td, J = 15.0, 8.0 Hz, 1H), 5.64-5.28 (m, 2H), 3.85 (t, J = 15.0 Hz, 3H), 3.63-3.61 (m, 3H), 3.46-3.31 (m, 2H), 2.53 (q, J = 15.0 Hz, 3H), 2.16-2.08 (m, 3H), 1.23 (t, J = 7.3 Hz, 3H).
[0596] Compound 215: 7.79 (d, J = 8.0 Hz, 1H), 7.30 (d, J = 8.0 Hz, 1H), 5.34 (s, 2H), 3.80 (d, J = 4.4 Hz, 3H), 3.60-3.55 (m, 4H), 2.46 (s, 3H), 2.06 (d, J = 4.1 Hz, 3H), 1.28-1.19 (m, 6H).
[0597] Compound 218: 7.86 (d, J = 8.0 Hz, 1H), 7.54 (s, 1H), 7.33 (d, J = 8.0 Hz, 1H), 5.40 (s, 2H), 3.82 (d, J = 3.0 Hz, 3H), 3.55 (s, 3H), 3.18 (d, J = 2.7 Hz, 3H), 2.42 (s, 3H), 2.10 (t, J = 4.0 Hz, 3H).
[0598] Compound 219: 7.82-7.80 (m, 1H), 7.54 (s, 1H), 7.32 (d, J = 8.0 Hz, 1H), 5.36 (s, 2H), 3.84 (s, 3H), 3.55 (s, 3H), 3.30 (q, J = 7.3 Hz, 2H), 2.42 (s, 3H), 2.09 (d, J = 3.0 Hz, 3H), 1.20 (t, J = 7.4 Hz, 3H).
[0599] Compound 220: 7.78 (d, J = 8.0 Hz, 1H), 7.53 (s, 1H), 7.31 (d, J = 8.2 Hz, 1H), 5.32 (s, 2H), 3.84 (s, 3H), 3.54 (s, 3H), 3.49 (t, J = 6.6 Hz, 1H), 2.41 (s, 3H), 2.09 (s, 3H), 1.23 (d, J = 6.6 Hz, 6H).
[0600] Compound 221: 7.85 (dd, J = 15.1, 6.9 Hz, 1H), 7.67-7.57 (m, 1H), 7.39-7.29 (m, 1H), 5.32 (d, J = 36.6 Hz, 2H), 3.82 (t, J = 15.1 Hz, 3H), 3.51 (t, J = 15.0 Hz, 3H), 3.20 (q, J = 14.9 Hz, 3H), 2.49-2.42 (m, 1H), 2.13-2.05 (m, 3H), 0.98-0.85 (m, 4H).
[0601] Compound 222: 7.79 (d, J = 8.0 Hz, 1H), 7.67 (s, 1H), 7.32 (d, J = 8.0 Hz, 1H), 5.31 (d, J = 21.7 Hz, 2H), 3.83 (s, 3H), 3.58-3.53 (m, 1H), 3.50 (s, 3H), 2.43-2.40 (m, 1H), 2.07 (s, 3H), 1.21 (d, J = 6.6 Hz, 6H), 0.94-0.92 (m, 2H), 0.89 (dt, J = 8.2, 2.6 Hz, 2H).
[0602] Compound 223: 8.03 (d, J = 8.0 Hz, 1H), 7.42 (d, J = 8.2 Hz, 1H), 6.38 (s, 1H), 5.37 (s, 2H), 4.05 (s, 3H), 3.65 (s, 3H), 3.24 (s, 3H), 2.38 (s, 3H), 2.29 (s, 3H), 2.17 (s, 3H).
[0603] Compound 224: 7.98 (d, J = 8.0 Hz, 1H), 7.41 (d, J = 8.0 Hz, 1H), 6.40 (s, 1H), 5.34 (s, 2H), 4.05 (s, 3H), 3.65 (s, 3H), 3.37 (q, J = 7.4 Hz, 2H), 2.36 (s, 3H), 2.30 (s, 3H), 2.16 (s, 3H), 1.26 (t, J = 7.3 Hz, 3H).
[0604] Compound 225: 7.99-7.94 (m, 1H), 7.43-7.38 (m, 1H), 6.43 (t, J = 15.0 Hz, 1H), 5.36-5.27 (m, 2H), 4.06 (s, 3H), 3.65 (s, 3H), 3.63-3.56 (m, 1H), 2.34 (s, 3H), 2.31 (s, 3H), 2.15-2.13 (m, 3H), 1.32-1.26 (m, 6H).
[0605] Compound 226: 7.98 (dd, J = 14.8, 6.9 Hz, 1H), 7.48-7.43 (m, 1H), 6.48 (t, J = 15.0 Hz, 1H), 5.36 (d, J = 14.8 Hz, 2H), 4.09-4.05 (m, 3H), 3.62-3.61 (m, 4H), 2.31 (s, 3H), 2.15-2.12 (m, 3H), 2.05-1.98 (m, 1H), 1.30 (d, J = 6.6 Hz, 6H), 0.97-0.92 (m, 2H), 0.83-0.78 (m, 2H).
[0606] Compound 227: 7.88 (d, J = 8.2 Hz, 1H), 7.38 (d, J = 8.0 Hz, 1H), 6.34 (d, J = 0.5 Hz, 1H), 5.40 (s, 2H), 3.85 (s, 3H), 3.63 (d, J = 9.6 Hz, 3H), 3.21 (s, 3H), 2.56 (s, 3H), 2.29 (d, J = 0.5 Hz, 3H), 2.15 (s, 3H).
[0607] Compound 228: 7.75 (d, J = 8.0 Hz, 1H), 7.30 (d, J = 8.0 Hz, 1H), 6.28 (d, J = 0.5 Hz, 1H), 5.28 (d, J = 6.0 Hz, 2H), 3.78 (s, 3H), 3.55 (s, 3H), 3.26 (q, J = 7.4 Hz, 2H), 2.49 (s, 3H), 2.23 (d, J = 0.5 Hz, 3H), 2.06 (d, J = 4.1 Hz, 3H), 1.15 (t, J = 7.4 Hz, 3H).
[0608] Compound 229: 7.84-7.78 (m, 1H), 7.36 (dd, J = 15.1, 6.9 Hz, 1H), 6.35 (t, J = 14.8 Hz, 1H), 5.45-5.27 (m, 2H), 3.86 (s, 3H), 3.62 (s, 3H), 3.60-3.55 (m, 1H), 2.58-2.51 (m, 3H), 2.32-2.31 (m, 3H), 2.13 (d, J = 4.1 Hz, 3H), 1.24 (t, J = 7.0 Hz, 6H).
[0609] Compound 231: 7.88 (d, J = 8.0 Hz, 1H), 7.58 (q, J = 0.8 Hz, 1H), 7.34 (d, J = 8.2 Hz, 1H), 7.05-7.04 (m, 1H), 6.51 (q, J = 1.7 Hz, 1H), 5.35 (s, 2H), 3.58 (s, 3H), 3.17 (s, 3H), 2.39 (s, 3H), 2.11 (d, J = 5.2 Hz, 3H).
[0610] Compound 233: 7.82 (d, J = 8.0 Hz, 1H), 7.59 (q, J = 0.8 Hz, 1H), 7.33 (d, J = 8.2 Hz, 1H), 7.06 (d, J = 3.6 Hz, 1H), 6.51 (q, J = 1.7 Hz, 1H), 5.31 (s, 2H), 3.58 (s, 3H), 3.32-3.27 (m, 2H), 2.38 (s, 3H), 2.09 (d, J = 5.5 Hz, 3H), 1.19 (q, J = 7.4 Hz, 3H).
[0611] Compound 234: 7.88 (d, J = 8.2 Hz, 1H), 7.67 (q, J = 0.8 Hz, 1H), 7.39 (d, J = 8.0 Hz, 1H), 7.14-7.13 (m, 1H), 6.59 (q, J = 1.7 Hz, 1H), 5.36 (s, 2H), 3.65 (s, 3H), 3.60 (t, J = 6.7 Hz, 1H), 2.44 (s, 3H), 2.17 (d, J = 14.8 Hz, 3H), 1.30-1.26 (m, 6H).
[0612] Compound 235: 7.97 (d, J = 8.2 Hz, 1H), 7.65 (q, J = 0.8 Hz, 1H), 7.45 (d, J = 8.2 Hz, 1H), 7.14 (d, J = 3.6 Hz, 1H), 6.58 (q, J = 1.7 Hz, 1H), 5.43 (s, 2H), 3.61-3.59 (m, 3H), 3.25 (s, 3H), 2.37 (s, 1H), 2.19-2.16 (m, 3H), 1.01-0.97 (m, 2H), 0.93-0.89 (m, 2H).
[0613] Compound 236: 7.94(d,J=8.2Hz,1H),7.79(q,J=0.8Hz,1H),7.53(d,J=8.0Hz,1H),7.24(dd,J=3.6,0.5Hz,1H),6.62(q,J=1.7Hz,1H),5.32(s,2H), 3.54(d,J=5.5Hz,3H),3.31(q,J=7.3Hz,2H),2.18(d,J=2.7Hz,1H),2.13(s,3H),1.14(q,J=7.5Hz,3H),0.87-0.85(m,2H),0.84-0.79(m,2H).
[0614] Compound 237: 7.81 (d, J = 8.2 Hz, 1H), 7.59 (q, J = 0.8 Hz, 1H), 7.32 (d, J = 8.0 Hz, 1H), 7.07 (dd, J = 3.7, 0.7 Hz, 1H), 6.51 (q, J = 1.8 Hz, 1H), 5.29 (t, J = 14.8 Hz, 2H), 3.85 (q, J = 7.2 Hz, 2H), 3.56-3.49 (m, 1H), 2.37 (d, J = 7.4 Hz, 3H), 2.07 (d, J = 4.1 Hz, 3H), 1.37-1.33 (m, 3H), 1.21 (dd, J = 15.0, 8.1 Hz, 6H).
[0615] Compound 238: 7.84 (d, J = 8.0 Hz, 1H), 7.67 (dd, J = 4.9, 1.1 Hz, 1H), 7.55 (dd, J = 3.8, 1.1 Hz, 1H), 7.33 (d, J = 8.2 Hz, 1H), 7.08 (dd, J = 4.9, 3.8 Hz, 1H), 5.27 (s, 2H), 3.58 (s, 3H), 3.12 (s, 3H), 2.43 (s, 3H), 2.09 (s, 3H).
[0616] Compound 239: 7.79 (d, J = 8.0 Hz, 1H), 7.68 (dd, J = 5.1, 1.2 Hz, 1H), 7.56 (dd, J = 3.8, 1.4 Hz, 1H), 7.32 (d, J = 8.2 Hz, 1H), 7.08 (dd, J = 4.9, 3.8 Hz, 1H), 5.24 (s, 2H), 3.58 (s, 3H), 3.25 (q, J = 7.3 Hz, 2H), 2.42 (s, 3H), 2.08 (s, 3H), 1.15 (t, J = 7.3 Hz, 3H).
[0617] Compound 240: 7.84 (d, J = 8.0 Hz, 1H), 7.75 (dd, J = 4.9, 1.4 Hz, 1H), 7.63 (dd, J = 3.8, 1.1 Hz, 1H), 7.38 (d, J = 8.2 Hz, 1H), 7.16 (dd, J = 4.9, 3.8 Hz, 1H), 5.29 (d, J = 8.0 Hz, 2H), 3.66 (d, J = 5.5 Hz, 3H), 3.61-3.56 (m, 1H), 2.48 (s, 3H), 2.14 (s, 3H), 1.26 (d, J = 6.9 Hz, 6H).
[0618] Compound 241: 7.85 (d, J = 8.2 Hz, 1H), 7.66 (dd, J = 4.9, 1.1 Hz, 1H), 7.56 (dd, J = 3.8, 1.1 Hz, 1H), 7.37 (d, J = 8.0 Hz, 1H), 7.07 (dd, J = 4.9, 3.9 Hz, 1H), 5.33-5.25 (m, 2H), 3.53 (s, 3H), 3.12 (s, 3H), 2.43-2.34 (m, 1H), 2.09 (s, 3H), 0.93 (td, J = 5.3, 3.2 Hz, 2H), 0.90-0.85 (m, 2H).
[0619] Compound 242: 7.80 (t, J = 4.0 Hz, 1H), 7.68-7.65 (m, 1H), 7.57 (td, J = 3.9, 1.2 Hz, 1H), 7.37-7.35 (m, 1H), 7.09-7.07 (m, 1H), 5.29-5.26 (m, 2H), 3.53 (s, 3H), 3.25 (q, J = 7.3 Hz, 2H), 2.38-2.31 (m, 1H), 2.07 (t, J = 4.0 Hz, 3H), 1.16 (t, J = 7.4 Hz, 3H), 0.95-0.90 (m, 2H), 0.88-0.83 (m, 2H).
[0620] Compound 243: 7.80-7.77 (m, 1H), 7.68-7.66 (m, 1H), 7.58 (dd, J = 3.8, 1.1 Hz, 1H), 7.35 (dd, J = 8.1, 2.6 Hz, 1H), 7.09 (dd, J = 4.9, 3.8 Hz, 1H), 5.21 (d, J = 14.8 Hz, 2H), 3.53 (d, J = 2.5 Hz, 3H), 3.52-3.47 (m, 1H), 2.36-2.29 (m, 1H), 2.07-2.06 (m, 3H), 1.20-1.16 (m, 6H), 0.95-0.90 (m, 2H), 0.88-0.82 (m, 2H).
[0621] Compound 244: 7.91 (d, J = 8.2 Hz, 1H), 7.83 (q, J = 0.7 Hz, 1H), 7.41 (t, J = 1.6 Hz, 1H), 7.33 (d, J = 8.0 Hz, 1H), 6.45 (q, J = 0.9 Hz, 1H), 5.35 (s, 2H), 3.56 (s, 3H), 3.16 (s, 3H), 2.37 (s, 3H), 2.11 (s, 3H).
[0622] Compound 246: 7.87-7.86 (m, 1H), 7.85-7.83 (m, 1H), 7.42 (t, J = 1.8 Hz, 1H), 7.31 (d, J = 8.2 Hz, 1H), 6.45 (q, J = 0.9 Hz, 1H), 5.27 (s, 2H), 3.56 (s, 3H), 3.54-3.48 (m, 1H), 2.34 (s, 3H), 2.09 (d, J = 3.6 Hz, 3H), 1.22 (dd, J = 15.0, 8.1 Hz, 6H).
[0623] Compound 247: 7.92 (d, J = 8.2 Hz, 1H), 7.86 (q, J = 0.7 Hz, 1H), 7.41 (t, J = 1.6 Hz, 1H), 7.37 (d, J = 8.0 Hz, 1H), 6.48 (q, J = 0.8 Hz, 1H), 5.36 (s, 2H), 3.51 (s, 3H), 3.16 (s, 3H), 2.25-2.21 (m, 1H), 2.11 (s, 3H), 0.92-0.88 (m, 2H), 0.83-0.79 (m, 2H).
[0624] Compound 248: 7.92-7.83 (m, 2H), 7.43-7.40 (m, 1H), 7.39-7.34 (m, 1H), 6.48 (td, J = 15.0, 1.6 Hz, 1H), 5.36-5.27 (m, 2H), 3.52 (t, J = 15.0 Hz, 3H), 3.30 (td, J = 15.0, 7.6 Hz, 2H), 2.25-2.17 (m, 1H), 2.13-2.05 (m, 3H), 1.22-1.15 (m, 3H), 0.95-0.88 (m, 2H), 0.85-0.76 (m, 2H).
[0625] Compound 249: 8.09 (t, J = 1.1 Hz, 1H), 7.92 (d, J = 8.0 Hz, 1H), 7.57 (t, J = 1.8 Hz, 1H), 7.51 (d, J = 8.2 Hz, 1H), 6.63 (q, J = 0.9 Hz, 1H), 5.30 (s, 2H), 3.53 (t, J = 4.1 Hz, 3H), 2.22 (t, J = 5.1 Hz, 1H), 2.13-2.09 (m, 3H), 1.26-1.23 (m, 1H), 1.21-1.14 (m, 6H), 0.88-0.85 (m, 2H), 0.85-0.80 (m, 2H).
[0626] Compound 250: 7.93 (q, J = 1.4 Hz, 1H), 7.85 (dd, J = 14.8, 6.9 Hz, 1H), 7.35-7.29 (m, 2H), 7.17-7.14 (m, 1H), 5.25-5.20 (m, 2H), 3.57 (s, 3H), 3.12 (s, 3H), 2.42 (s, 3H), 2.10 (s, 3H).
[0627] Compound 251: 8.02 (q, J = 1.4 Hz, 1H), 7.84 (d, J = 8.0 Hz, 1H), 7.42-7.38 (m, 2H), 7.23 (dd, J = 5.1, 1.2 Hz, 1H), 5.27 (s, 2H), 3.65 (d, J = 5.8 Hz, 3H), 3.55 (t, J = 6.9 Hz, 1H), 2.46 (s, 3H), 2.16 (d, J = 8.8 Hz, 3H), 1.38-1.33 (m, 1H), 1.29-1.26 (m, 6H).
[0628] Compound 252: 8.00 (q, J = 1.4 Hz, 1H), 7.91 (dd, J = 14.8, 6.9 Hz, 1H), 7.44-7.39 (m, 1H), 7.38-7.35 (m, 1H), 7.23-7.21 (m, 1H), 5.33 (s, 2H), 3.58 (s, 3H), 3.18 (s, 3H), 2.49-2.37 (m, 1H), 2.14 (d, J = 4.4 Hz, 3H), 1.02-0.97 (m, 2H), 0.95-0.89 (m, 2H).
[0629] Compound 253: 8.03 (q, J = 1.4 Hz, 1H), 7.88 (d, J = 8.2 Hz, 1H), 7.43-7.41 (m, 1H), 7.39 (q, J = 2.7 Hz, 1H), 7.26-7.24 (m, 1H), 5.31 (s, 2H), 3.60-3.56 (m, 3H), 3.33 (q, J = 7.4 Hz, 2H), 2.39 (s, 1H), 2.17-2.11 (m, 3H), 1.27-1.20 (m, 3H), 1.02-0.98 (m, 2H), 0.96-0.90 (m, 2H).
[0630] Compound 254: 8.04 (q, J = 1.5 Hz, 1H), 7.86 (d, J = 8.2 Hz, 1H), 7.43-7.38 (m, 2H), 7.26 (dd, J = 5.1, 1.2 Hz, 1H), 5.29 (s, 2H), 3.61-3.58 (m, 3H), 2.37 (s, 1H), 2.15 (d, J = 5.5 Hz, 3H), 1.33 (t, J = 6.2 Hz, 1H), 1.30-1.21 (m, 6H), 1.01-0.98 (m, 2H), 0.95-0.89 (m, 2H).
[0631] The compound of the general formula (I-3) of the present invention can be prepared by the following method:
[0632]
[0633] In the above formula, the compound of general formula II and R 10 A 5 H in a base and a suitable solvent at a temperature of -10°C to 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 sulfide, sodium carbonate, potassium carbonate or triethylamine.
[0634] The preparation method of the compound of formula II is as follows:
[0635]
[0636]
[0637] The compound of general formula III in the above formula reacts with a suitable chlorinating agent at 0°C to boiling point for 0.5 to 4 hours to obtain a compound of general formula II. The suitable chlorinating agent is selected from thionyl chloride, oxalyl chloride or phosphorus trichloride.
[0638] The preparation method of the compound of formula III is as follows:
[0639]
[0640] The compound of general formula IV in the above formula is reacted in a suitable solvent at a temperature of -10°C to boiling point for 0.5 to 24 hours under the action of a base and a catalyst to obtain a compound of general formula III. The suitable solvent is selected from dichloromethane, 1,2-dichloroethane, chloroform, carbon tetrachloride, benzene, toluene, ethyl acetate, acetonitrile, tetrahydrofuran, dioxane, N,N-dimethylformamide or dimethyl sulfoxide. The suitable base is selected from sodium carbonate, potassium carbonate or triethylamine. The suitable catalyst is selected from sodium carbonate, potassium carbonate or acetone cyanohydrin.
[0641] The preparation method of the compound of formula IV is as follows:
[0642]
[0643] In the above formula, the compound of general formula V is first reacted with an acyl halide reagent in a suitable solvent at a temperature of -10°C to the boiling point of a suitable solvent for 0.5 to 24 hours to obtain 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 obtained above is reacted with 1,3-cyclohexanedione in the same or different solvent at a temperature of -10°C to the boiling point of the corresponding solvent for 0.5 to 24 hours to obtain the compound of general formula IV. The suitable base is selected from triethylamine, pyridine, sodium carbonate, potassium carbonate, sodium methoxide or potassium tert-butoxide.
[0644] The preparation method of the compound of formula V is as follows:
[0645]
[0646] The compound of formula VI (refer to "Pesticides", 2017, 56 (5): 326-327, 379 Synthesis of cornfield herbicide cyclosulfone) 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 a suitable solvent for 0.5 to 24 hours to obtain a 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.
[0647] The preparation method of the compound of general formula I-2 is as follows:
[0648]
[0649] In the above formula, the compound of general formula VIII and the compound of general formula R 6Cl is reacted in a suitable solvent under the action of a base for 0.5 to 24 hours to obtain a compound of general 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.
[0650] A 3 Taking O as an example, the preparation method of the compound of formula VIII is as follows:
[0651]
[0652] 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 the compound of formula IV, which will not be described in detail in this application.
[0653] The compound of general formula I-1 and the compound of formula III are tautomers due to different environmental conditions, for example, keto-enol tautomerism occurs due to different solvents, pH, etc.
[0654] The herbicidal composition, oxadiazolone compound and use thereof provided by the present invention are further described below with reference to the examples.
[0655] Example 1 Synthesis of Compound 1
[0656] (1) Synthesis of 2-chloro-3-[(5-methyl-2-oxo-1,3,4-oxadiazol-3(2H)yl)methyl)]-4-methanesulfonylbenzoic acid
[0657]
[0658] 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 value 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%.
[0659] (2) 2-Chloro-3-[(5-methyl-2-oxo-1,3,4-oxadiazol-3(2H)yl)methyl)]-4-methanesulfonylbenzoate (3-oxocyclohex-1-ene)
[0660]
[0661] 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 to the reaction flask, and thionyl chloride (14.3 g, 120 mmol) was slowly added. The mixture was heated under reflux for 4 hours, and the solvent and excess thionyl chloride were evaporated under reduced pressure. Dichloromethane (60 ml) and 1,3-cyclohexanedione (2.3 g, 20.5 mmol) were added, and triethylamine (3.2 g, 32 mmol) was added dropwise. The mixture was stirred at room temperature for 1 hour, and water (50 ml) was added. The aqueous phase was extracted twice with dichloromethane (30 ml*2). The oil phases were combined, and the solvent was evaporated to obtain 8.3 g of light yellow solid, which was directly used in the next step.
[0662] (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)
[0663]
[0664] Add dichloromethane (60 ml), triethylamine (2.4 g, 24 mmol), 2 drops of acetone cyanohydrin into the reaction flask, add 8.3 g of the solid obtained in the previous step, stir at room temperature overnight, add water (60 ml) and stir for half an hour, adjust the pH to 7-8 with 10% dilute hydrochloric acid, extract the aqueous phase twice with ethyl acetate (60 ml * 2), combine the organic phases, wash with saturated brine (60 ml), dry over anhydrous magnesium sulfate, and evaporate the solvent under reduced pressure to obtain 8.1 g of light yellow solid with a purity of 97%.
[0665] Example 2 Synthesis of Compound 53
[0666] (1) 3-{2-chloro-3-[(2-chloro-6-oxocyclohex-1-enyl)carbonyl]-6-(methylsulfonyl)benzyl}-5-methyl-1,3,4-oxadiazol-2(3H)-alkane
[0667]
[0668] 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) were added to a reaction flask, and 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%.
[0669] (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)
[0670]
[0671] In a 100 ml four-necked flask, 3-{2-chloro-3-[(2-chloro-6-oxocyclohex-1-enyl)carbonyl]-6-(methylsulfonyl)benzyl}-5-methyl-1,3,4-oxadiazole-2(3H)-alkane (6 g, 13 mmol), 30 g HMPA, and 1.6 g benzyl mercaptan were added and stirred evenly. The temperature was lowered to 0°C, and 0.38 g of sodium hydrogen was slowly added to the four-necked flask in batches. The sample was measured until the reaction of the raw materials was completed, and the pH value was adjusted to 3 with acid water. The mixture was extracted with ethyl acetate, and the ethyl acetate phase was collected and rotary evaporated at a negative pressure to obtain a crude product. The product was stirred overnight with a dichloromethane and sodium bicarbonate aqueous solution, and the dichloromethane phase was collected and rotary evaporated to obtain 5.6 g of a yellow solid with a purity of 90%.
[0672] Example 3 Synthesis of Compound 100
[0673] (1) Synthesis of 2-chloro-3-[(5-methyl-2-oxo-1,3,4-oxadiazol-3(2H)yl)methyl)]-4-isopropylsulfonylbenzoic acid
[0674]
[0675] 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) were added to a reaction flask. The temperature was raised to reflux for 3 hours, and the solvent was evaporated under reduced pressure. Water (50 ml) was added and stirred, 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 white solid with a yield of 80%.
[0676] (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)
[0677]
[0678] 2-Chloro-3-[(5-methyl-2-oxo-1,3,4-oxadiazole-3(2H)yl)methyl)]-4-isopropylsulfonylbenzoic acid (7.5 g, 20 mmol) and dichloroethane (50 ml) were added to the reaction flask, and oxalyl chloride (7.6 g, 60 mmol) was slowly added. The mixture was heated under reflux for 4 hours, and the solvent and excess oxalyl chloride were evaporated under reduced pressure. Dichloroethane (60 ml) and 1,3-dimethyl-5-hydroxypyrazole (2.3 g, 20.5 mmol) were added, and triethylamine (3.2 g, 32 mmol) was added dropwise. The mixture was stirred at room temperature for 1 hour, and water (50 ml) was added. The aqueous phase was extracted twice with dichloroethane (30 ml*2). The oil phases were combined, the solvent was evaporated, and the residue was separated by column chromatography to obtain 6.1 g of light yellow solid, with a yield of 65%.
[0679] (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)
[0680]
[0681] 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), acetone cyanohydrin (2 ml) were added to a reaction flask, and the mixture was reacted at room temperature for 12 hours. Water extraction (60 ml) was added to the reaction solution, and the mixture was stirred for half an hour. The pH value was adjusted to 2-3 with 10% dilute hydrochloric acid, and 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%.
[0682] Example 4 Synthesis of Compound 171
[0683]
[0684] 1-Methyl-3-trifluoromethyl-4-pyrazolecarboxylic acid (4.5 g, 23 mmol) and dichloroethane (80 ml) were added to the reaction flask, 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%).
[0685] Example 5 Determination of herbicidal activity
[0686] Seeds of broadleaf weeds (ramie, nightshade) or grass weeds (crabgrass, barnyard grass) are sown in plastic cups filled with nutrient soil, covered with soil, suppressed, and watered, and then cultured in a greenhouse according to conventional methods. After the weeds reach the 2-3 leaf stage, the stems and leaves are sprayed. The tested compounds of the present invention are dissolved in acetone, and then Tween 80 is added, 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 is repeated 3 times. After natural shade drying, they are placed in a greenhouse and managed according to conventional methods, the growth and development of the weeds are observed, and the control effect of the tested agents on the weeds is regularly visually observed, and expressed as 0-100%, with "0" representing no control effect and "100%" representing complete killing or severe inhibition.
[0687] The test results show that the compounds of general formula I generally have high control effects on broadleaf 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, 231, 233, 238, 244, 246, 250, when applied at a rate of 300 g ai / ha, have good control effects on crabgrass, with the control effects being greater than 80%; such as compounds 1, 5, 32, 56, 58, 59, 68, 72, 82, 96, 100, 149, 150, 152, 153, 154, 166, 194, 215, 223, 224, 227, 233, 238, 244, 246, 250, when applied at a rate of 300 g ai / ha, have good control effects on crabgrass, with the control effects being greater than 80%; ai / ha, it has a good control effect on barnyard grass, and the control effect is greater than 80%; for example, compounds 1, 5, 48, 53, 58, 68, 72, 96, 100, 150, 152, 154, 166, 171, 178, 180, 182, 185, 187, 190, 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 have a good control effect on velvetleaf and nightshade at an application rate of 300 g ai / ha, and the control effect is greater than 90%.
[0688] According to the above test method, compounds 1, 32, 49, 166, 194, 204, 218, 224 and control compounds A, B, and C were selected for herbicidal activity determination. The activity data on velvetleaf, Solanum nigrum, Digitaria tangutica, and Echinochloa crusgalli are shown in Table 4, which shows the post-emergence weed test results of the compounds provided in the examples of the present application.
[0689] Table 4 Post-emergence weed test results of the compounds provided in the examples of this application
[0690]
[0691]
[0692] Wherein, the control compound A is:
[0693]
[0694] The control compound B is:
[0695]
[0696] The control compound C is:
[0697] It can be seen from Table 4 that compared with the control compounds A, B and C, the compounds 1, 32, 49, 166, 194, 204, 218 and compound 224 provided in the present application have good herbicidal activity against velvetleaf, Solanum nigrum, Digitaria tangutica, Echinochloa crusgalli, etc. at different dosages.
[0698] Example 6 Determination of safety of corn and rice
[0699] Corn and rice seeds are 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 crop reaches the 2-3 leaf stage, the stems and leaves are sprayed. The tested compounds of the present invention are dissolved in acetone, and then Tween 80 is added, diluted with a certain amount of water to form a solution of a certain solubility, and sprayed on the plants with a spray tower. The test is repeated 3 times. After natural shade drying, they are placed in a greenhouse and managed according to conventional methods, and the growth and development of corn and rice are observed. The safety of the tested agents on corn and rice is visually inspected regularly. Safety grading standard: 0-100% is used to represent, "0" represents no damage to the crop, and "100%" represents complete killing or severe inhibition of the crop. Some test results are shown in Table 5, which is the corn and rice safety test results of the compounds provided in the examples of the present application.
[0700] Table 5 Corn and rice safety test results of the compounds provided in the examples of this application
[0701]
[0702]
[0703] The control compound A is:
[0704]
[0705] The control compound B is:
[0706]
[0707] The control compound C is:
[0708]
[0709] It can be seen from Table 5 that compared with the control compounds A, B and C, the compounds 6, 58, 100, 224, 228 and compound 233 provided in the present application had no obvious inhibitory effect on corn and rice at different dosages.
[0710] In summary, the general compound of the present invention has excellent herbicidal activity against various agricultural weeds and is safe for various crops including corn and rice.
[0711] The above description is only a preferred specific implementation manner of the present invention, but the protection scope of the present invention is not limited thereto. Any technician familiar with the technical field can make equivalent replacements or changes according to the technical scheme and inventive concept of the present invention within the technical scope disclosed by the present invention, which should be covered by the protection scope of the present invention.
Claims
1. Oxadiazolone compounds represented by formula (I): in, R1 and R2 are independently selected from C1-C6 alkyl or C3-C6 cycloalkyl; A3 is selected from O; R4 is selected from hydrogen, C1-C6 alkyl, C3-C6 cycloalkyl or C1-C6 alkoxy; R5 is selected from C1-C6 alkyl or C3-C6 cycloalkyl; R6 is selected from the structure shown below: 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 is selected from H, halogen, C1-C4 alkyl, C3-C6 cycloalkyl or C1-C4 haloalkyl, and the halogen of the C1-C4 haloalkyl is selected from F substitution; m is an integer of 1-3.
2. The oxadiazolone compound represented by formula (I) according to claim 1, characterized in that: R1 and R2 are independently selected from -CH3, -CH2CH3, -CH2CH2CH3, -CH(CH3)2, -C(CH3)3, -CH2CH2CH2CH3.
3. The oxadiazolone compound of formula (I) according to claim 1, characterized in that Selected from the following compounds: Compound 154: A3 = O, R1 = CH3, R2 = CH3, R4 = CH3, R5 = CH3, Compound 155: A3 = O, R1 = CH2CH3, R2 = CH3, R4 = CH3, R5 = CH3, Compound 156: A3 = O, R1 = CH2CH2CH3, R2 = CH3, R4 = CH3, R5 = CH3, Compound 157: A3 = O, R1 = CH(CH3)2, R2 = CH3, R4 = CH3, R5 = CH3, Compound 158: A3=O, R1=CH3, R2=CH3, R4=H, R5=CH3, Compound 159: A3=O, R1=CH2CH3, R2=CH3, R4=H, R5=CH3, Compound 160: A3 = O, R1 = CH2CH2CH3, R2 = CH3, R4 = H, R5 = CH3, Compound 161: A3=O, R1=CH(CH3)2, R2=CH3, R4=H, R5=CH3, Compound 162: A3=O, R1=CH3, R2=CH3, R5=CH3, Compound 163: A3=O, R1=CH2CH3, R2=CH3, R5=CH3, Compound 164: A3=O, R1=CH2CH2CH3, R2=CH3, R5=CH3, Compound 165: A3=O, R1=CH(CH3)2, R2=CH3, R5=CH3, Compound 166: A3 = O, R1 = CH3, R2 = CH3, R4 = CH3, R5 = CH3, Compound 167: A3 = O, R1 = CH2CH3, R2 = CH3, R4 = CH3, R5 = CH3, Compound 168: A3 = O, R1 = CH2CH2CH3, R2 = CH3, R4 = CH3, R5 = CH3, Compound 169: A3 = O, R1 = CH(CH3)2, R2 = CH3, R4 = CH3, R5 = CH3, Compound 170: A3=O, R1=CH3, R2=CH3, R4=H, R5=CH3, Compound 171: A3=O, R1=CH2CH3, R2=CH3, R4=H, R5=CH3, Compound 172: A3 = O, R1 = CH2CH2CH3, R2 = CH3, R4 = H, R5 = CH3, Compound 173: A3=O, R1=CH(CH3)2, R2=CH3, R4=H, R5=CH3, Compound 174: A3=O, R1=CH3, R2=CH3, R5=CH3, Compound 175: A3=O, R1=CH2CH3, R2=CH3, R5=CH3, Compound 176: A3=O, R1=CH2CH2CH3, R2=CH3, R5=CH3, Compound 177: A3=O, R1=CH(CH3)2, R2=CH3, R5=CH3, Compound 178: A3 = O, R1 = CH3, R2 = CH3, R4 = CH3, R5 = CH3, Compound 179: A3 = O, R1 = CH2CH2CH3, R2 = CH3, R4 = CH3, R5 = CH3, Compound 180: A3=O, R1=CH3, R2=CH3, R4=H, R5=CH3, Compound 181: A3 = O, R1 = CH2CH2CH3, R2 = CH3, R4 = H, R5 = CH3, Compound 182: A3=O, R1=CH3, R2=CH3, R5=CH3, Compound 183: A3=O, R1=CH2CH2CH3, R2=CH3, R5=CH3, Compound 184: A3 = O, R1 = CH2CH3, R2 = CH3, R4 = CH3, R5 = CH3, Compound 185: A3 = O, R1 = CH(CH3)2, R2 = CH3, R4 = CH3, R5 = CH3, Compound 186: A3=O, R1=CH2CH3, R2=CH3, R4=H, R5=CH3, Compound 187: A3=O, R1=CH(CH3)2, R2=CH3, R4=H, R5=CH3, Compound 188: A3=O, R1=CH2CH3, R2=CH3, R5=CH3, Compound 189: A3=O, R1=CH(CH3)2, R2=CH3, R5=CH3, Compound 190: A3 = O, R1 = CH2CH3, R2 = CH3, R4 = CH3, R5 = CH2CH3, Compound 191: A3=O, R1=CH3, R2=CH3, R4=H, R5=CH2CH3, Compound 192: A3=O, R1=CH2CH2CH3, R2=CH3, R5=CH2CH3, Compound 193: A3=O, R1=CH(CH3)2, R2=CH3, R5=CH2CH3, Compound 194: A3 = O, R1 = CH3, R2 = CH3, R4 = CH3, R5 = CH3, Compound 195: A3 = O, R1 = CH2CH3, R2 = CH3, R4 = CH3, R5 = CH3, Compound 196: A3 = O, R1 = CH2CH2CH3, R2 = CH3, R4 = CH3, R5 = CH3, Compound 197: A3 = O, R1 = CH(CH3)2, R2 = CH3, R4 = CH3, R5 = CH3, Compound 198: A3=O, R1=CH3, R2=CH3, R4=H, R5=CH3, Compound 199: A3=O, R1=CH2CH3, R2=CH3, R4=H, R5=CH3, Compound 200: A3=O, R1=CH(CH3)2, R2=CH3, R4=H, R5=CH3, Compound 201: A3=O, R1=CH3, R2=CH3, R5=CH3, Compound 202: A3=O, R1=CH2CH3, R2=CH3, R5=CH3, Compound 203: A3=O, R1=CH(CH3)2, R2=CH3, R5=CH3, Compound 204: A3 = O, R1 = CH3, R2 = CH3, R4 = CH3, R5 = CH3, Compound 205: A3 = O, R1 = CH2CH3, R2 = CH3, R4 = CH3, R5 = CH3, Compound 206: A3 = O, R1 = CH(CH3)2, R2 = CH3, R4 = CH3, R5 = CH3, Compound 207: A3=O, R1=CH3, R2=CH3, R4=H, R5=CH3, Compound 208: A3=O, R1=CH2CH3, R2=CH3, R4=H, R5=CH3, Compound 209: A3 = O, R1 = CH2CH2CH3, R2 = CH3, R4 = H, R5 = CH3, Compound 210: A3=O, R1=CH(CH3)2, R2=CH3, R4=H, R5=CH3, Compound 211: A3=O, R1=CH2CH3, R2=CH3, R5=CH3, Compound 212: A3=O, R1=CH(CH3)2, R2=CH3, R5=CH3, Compound 213: A3 = O, R1 = CH3, R2 = CH3, R4 = CH3, R5 = CH3, Compound 214: A3 = O, R1 = CH2CH3, R2 = CH3, R4 = CH3, R5 = CH3, Compound 215: A3 = O, R1 = CH(CH3)2, R2 = CH3, R4 = CH3, R5 = CH3, Compound 216: A3=O, R1=CH3, R2=CH3, R5=CH3, Compound 217: A3=O, R1=CH(CH3)2, R2=CH3, R5=CH3, Compound 218: A3 = O, R1 = CH3, R2 = CH3, R4 = CH3, R5 = CH3, Compound 219: A3 = O, R1 = CH2CH3, R2 = CH3, R4 = CH3, R5 = CH3, Compound 220: A3 = O, R1 = CH(CH3)2, R2 = CH3, R4 = CH3, R5 = CH3, Compound 221: A3=O, R1=CH3, R2=CH3, R5=CH3, Compound 222: A3=O, R1=CH(CH3)2, R2=CH3, R5=CH3, Compound 223: A3 = O, R1 = CH3, R2 = CH3, R4 = CH3, R5 = CH3, Compound 224: A3 = O, R1 = CH2CH3, R2 = CH3, R4 = CH3, R5 = CH3, Compound 225: A3 = O, R1 = CH(CH3)2, R2 = CH3, R4 = CH3, R5 = CH3, Compound 226: A3=O, R1=CH(CH3)2, R2=CH3, R5=CH3, Compound 227: A3 = O, R1 = CH3, R2 = CH3, R4 = CH3, R5 = CH3, Compound 228: A3 = O, R1 = CH2CH3, R2 = CH3, R4 = CH3, R5 = CH3, Compound 229: A3 = O, R1 = CH(CH3)2, R2 = CH3, R4 = CH3, R5 = CH3, Compound 230: A3=O, R1=CH(CH3)2, R2=CH3, R5=CH3, Compound 231: A3 = O, R1 = CH3, R2 = CH3, R4 = CH3, R5 = CH3, Compound 232: A3 = S, R1 = CH3, R2 = CH3, R4 = CH3, R5 = CH3, Compound 233: A3 = O, R1 = CH2CH3, R2 = CH3, R4 = CH3, R5 = CH3, Compound 234: A3 = O, R1 = CH(CH3)2, R2 = CH3, R4 = CH3, R5 = CH3, Compound 235: A3=O, R1=CH3, R2=CH3, R5=CH3, Compound 236: A3=O, R1=CH2CH3, R2=CH3, R5=CH3, Compound 237: A3=O, R1=CH(CH3)2, R2=CH3, R5=CH3, Compound 238: A3 = O, R1 = CH3, R2 = CH3, R4 = CH3, R5 = CH3, Compound 239: A3 = O, R1 = CH2CH3, R2 = CH3, R4 = CH3, R5 = CH3, Compound 240: A3 = O, R1 = CH(CH3)2, R2 = CH3, R4 = CH3, R5 = CH3, Compound 241: A3=O, R1=CH3, R2=CH3, R5=CH3, Compound 242: A3=O, R1=CH2CH3, R2=CH3, R5=CH3, Compound 243: A3=O, R1=CH(CH3)2, R2=CH3, R5=CH3, Compound 244: A3 = O, R1 = CH3, R2 = CH3, R4 = CH3, R5 = CH3, Compound 245: A3 = S, R1 = CH3, R2 = CH3, R4 = CH3, R5 = CH3, Compound 246: A3 = O, R1 = CH(CH3)2, R2 = CH3, R4 = CH3, R5 = CH3, Compound 247: A3=O, R1=CH3, R2=CH3, R5=CH3, Compound 248: A3=O, R1=CH2CH3, R2=CH3, R5=CH3, Compound 249: A3=O, R1=CH(CH3)2, R2=CH3, R5=CH3, Compound 250: A3 = O, R1 = CH3, R2 = CH3, R4 = CH3, R5 = CH3, Compound 251: A3 = O, R1 = CH(CH3)2, R2 = CH3, R4 = CH3, R5 = CH3, Compound 252: A3=O, R1=CH3, R2=CH3, R5=CH3, Compound 253: A3=O, R1=CH2CH3, R2=CH3, R5=CH3, Compound 254: A3=O, R1=CH(CH3)2, R2=CH3, R5=CH3, 4. An oxadiazolone compound having the following structure, characterized in that: The oxadiazolone compound has the following structure: And the compound is selected from: Compound 1: R1=CH3, R2=CH3; Compound 6: R1=CH2CH3, R2=CH3.
5. Use of the oxadiazolone compound or its tautomer according to any one of claims 1 to 4 in controlling weeds.
6. The use according to claim 5, characterized in that The weeds are selected from one or more of broadleaf weeds and grass weeds.
7. A herbicidal composition comprising the oxadiazolone compound or its tautomer as claimed in any one of claims 1 to 4 and an auxiliary material:
8. A method for controlling weeds, characterized in that: include: Applying the herbicidal composition according to claim 7 to crops.
Citation Information
Patent Citations
type body, especially for typewriters.
CH230277A
Process for sensitizing silver halide emulsions, especially those with a high silver chloride content, by mixtures of sensitizers.
CH230278A
target for target practice
CH30207A
decorated watch box background
CH30217A
watch barrel
CH30219A