Substituted benzoyl (hetero)cyclic diones 机翻标题: 暂无翻译,请尝试点击翻译按钮。

公开号/公开日
US5801120 A 1998-09-01 [US5801120] / 1998-09-01
申请号/申请日
1989US-07411086 / 1989-09-22
发明人
LEE SHY-FUH;NISHIZAKA TAKASHI;KOMATSUBARA KENICHI;
申请人
SANDOZ;
主分类号
IPC分类号
A01N-035/06A01N-041/04A01N-041/10A01N-043/54A01N-043/90C07C-045/54C07C-045/67C07C-049/792C07C-049/813C07C-049/835C07C-049/84C07C-201/12C07C-205/45C07C-205/58C07C-309/66C07C-317/24C07C-323/22C07D-493/08
摘要
(US5801120) Substituted aryl or heteroaryl in particular benzoyl bicycloalkanediones and related compounds, intermediates therefor, synthesis thereof, and the use of said diones for the control of weeds.
机翻摘要
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地址
代理人
代理机构
;
优先权号
1988US-07182534 1988-04-18 1989HU-0001707 1989-04-10 1989US-07411086 1989-09-22
主权利要求
(US5801120) What is claimed is: 1.  A compound having the formula I  (Chemical Structure image '13' not included in text)  wherein, Ar is selected from the groups  (Chemical Structure image '14' not included in text)   X is oxygen, sulfur or C1-4 alkylene;  each of R1, R2, R3, R4, R9 and R10 is, independently, hydrogen, C1-8 alkyl or COOR16 ; R5 is C1-8 -alkyl, optionally substituted with one to six halogen atoms;  C1-8 alkoxy, optionally substituted with one to six halogen atoms;  C1-8 alkylcarbonyl;  C1-8 alkoxycarbonyl;  NR13 R14 ;  On S(O)n,R12 ;  NR15 SO2 R12 ;  halogen;  cyano;  or nitro; each of R6 and R7 is independently hydrogen or selected from the values of R5 ;  or R6 and R7 together form the group --Y--W--Z--; R8 is hydrogen, C1-8 alkyl, optionally substituted C1-8 alkylcarbonyl, optionally substituted C1-8 alkoxycarbonyl, C(O)NR13 R14, C1-8 alkylsulfonyl, P(O)--((OR11)2, R13 P(O)OR11 or optionally substituted benzoyl or a salt forming moiety; R11 is C1-8 alkyl; R12 is C1-8 alkyl, optionally substituted with one to six halogen atoms; each of R13, R14, R15 and R16 is, independently, hydrogen or C1-8 alkyl; each of R17 and R18 is independently hydrogen, halogen, or C1-8 alkyl optionally substituted with one to six halogen atoms;  or R17 and R18 together form an oxo group; each of R19 and R20 is, independently, hydrogen, halogen, or C1-8 alkyl optionally substituted with one to six halogen atoms; W is --(CR17 R18)t --(CR19 R20)t,-- or SO2 ; each of Y and Z is independently oxygen, sulfur, SO2, C.dbd.O or CR15 R16 ;  with the proviso that Y and Z are attached to adjacent carbons; n is zero or one; n' is zero, one or two; q is zero, one or two; t is one or two;  and t' is zero or one. 14. A method for selectively controlling weeds in rice which comprises applying to the weeds or their locus a herbicidally effective amount of a compound according to claim 1. 2. A compound according to claim 1 wherein R8 is hydrogen, C1-8 alkyl, C1-8 alkylcarbonyl, C1-8 alkoxycarbonyl, C(O)NR13 R14, C1-8 alkylsulfonyl, P(O)--(OR11)2, R13 P(O)OR11 or benzoyl. 3. A compound according to claim 1 wherein R8 is optionally substituted C1-8 alkylcarbonyl, optionally substituted C1-8 alkoxycarbonyl or optionally substituted benzoyl or is an ammonium salt derived from an amine of formula X  (Chemical Structure image '15' not included in text)  wherein each of R21, R22 and R23 represents independently hydrogen, C1-16 alkyl optionally substituted by one or more hydroxy groups, C2-4 alkenyl or R21 and R22 form together a C2-5 alkylene group which may optionally be interrupted by oxygen. 4. A compound according to claim 1 wherein Ar is the group  (Chemical Structure image '16' not included in text)  5.  A compound according to claim 4 wherein X is oxygen or C1-3 alkyl, q is one, and each of R1, R2, R3, R4, R9 and R10 is independently hydrogen or C1-4 alkyl. 6. A compound according to claim 5 wherein R5 is C1-4 alkyl optionally substituted with one to three halogen atoms, --(O)n --S(O)n,C1-4 alkyl, halogen, or nitro. 7. A compound according to claim 6 wherein R5 is methyl, CF3, bromo, chloro, nitro or OSO2 CH3 and R8 is hydrogen, C1-4 alkyl, C4-8 alkylcarbonyl or benzoyl. 8. A compound according to claim 7 wherein R6 is in the 3-position and is hydrogen, methoxy, chloro or OSO2 CH3, and R7 is in the 4-position and is methoxy, CF3, bromo, chloro, nitro, OSO2 R12 or NHSO2 R12 where R12 is methyl, CH2 Cl or CF3. 9. A compound according to claim 8 wherein X is oxygen or methylene, and each of R1, R2, R3, R4, R9 and R10 is independently hydrogen, methyl or ethyl. 10. A compound according to claim 4 wherein X is CH2, q is 1 or 2, R9 and R10 are hydrogen, R5 is nitro or chloro, R6 is hydrogen and R7 is fluoro, chloro, bromo, S--C1-4 alkyl, SO2 --C1-4 alkyl, OSO2 --C1-4 alkyl. 11. A compound according to claim 10 wherein R8 is hydrogen. 12. An agricultural composition comprising an effective amount of a compound according to claim 1 together with an agriculturally acceptable carrier. 13. A method for the control of weeds which comprises applying to the weed or its locus an herbicidally effective amount of a compound according to claim 1. 15. A compound according to claim 2 wherein R8 is other than hydrogen or a salt forming moiety. 16. A compound according to claim 2 wherein R7 is R12 SO2 O. 17. A compound according to claim 2 wherein R6 +R7 is a methylene dioxy group. 18. A compound according to claim 2 wherein q is 2. 19. A compound according to claim 4 wherein X is CH2 R1, R2, R3 and R4 are hydrogen R5 is methyl, CF3, C1-3 alkylsulfonyl, C1-3 alkylsulfonoxy, chloro, bromo or nitro R6 is hydrogen or together with R7 methylenedioxy R7 is chloro, fluoro, bromo, C1-4 alkylthio, C1-3 alkylsulfonyl or C1-3 alkylsulfonyloxy, or together with R6 methylenedioxy R9 and R10 are independently hydrogen or C1-3 alkyl q is one or two. 20. A compound according to claim 19 wherein R8 is hydrogen or a salt forming moiety. 21. A compound according to claim 19 wherein R8 is other than hydrogen or a salt forming moiety. 22. A compound according to claim 4 wherein R1, R2, R3, R4, R6, R8 and R9 are hydrogen, R5 is nitro, R7 is 4-chloro, R10 is hydrogen or methyl and X is CH2 or C(CH3)2. 23. An agricultural composition comprising an effective amount of a compound according to claim 2 together with an agriculturally acceptable carrier. 24. A herbicidal composition comprising a herbicidally active 3-(substituted benzoyl)-3:2:1-bicyclooctan-2,4-dione or a salt thereof and an inert carrier. 25. A herbicidal composition comprising a herbicidally active compound according to claim 2 and an inert carrier therefor. 26. A herbicidal composition comprising a herbicidally active compound according to claim 22 and an inert carrier therefor. 27. A method for the control of weeds which comprises applying to the weed or its locus a herbicidally effective amount of a compound of formula I according to claim 2. 28. The method of controlling undesirable vegetation comprising applying to the area where control is desired a herbicidally effective amount of a compound according to claim 2. 29. The method of controlling undesirable vegetation comprising applying to the area where control is desired a herbicidally effective amount of a compound according to claim 22. 30. The method of controlling undesirable vegetation comprising applying to the area where control is desired, a herbicidal composition comprising a herbicidally active 3-(substituted benzoyl)-3:2:1-bicyclooctan-2,4-dione or its salt and an inert carrier therefor. 31. The method of controlling undesirable vegetation comprising applying to the area where control is desired, a herbicidal composition comprising a herbicidally active compound according to claim 2. 32. The method of controlling undesirable vegetation comprising applying to the area where control is desired, a herbicidal composition comprising a herbicidally active compound according to claim 22. 33. A compound according to claim 1 wherein Ar represents the group  (Chemical Structure image '17' not included in text)  X is CH2 CH2 ;  q is zero; each of R1, R2, R9 and R10 is, independently, hydrogen or C1-4 alkyl; R5 is halogen;  C1-4 alkyl optionally substituted by 1 to 6 halogen atoms;  C1-4 alkoxy optionally substituted by 1 to 6 halogen atoms;  nitro;  cyano;  or OnS(O)n,R12 ; each of R6 and R7 is independently hydrogen;  halogen;  C1-4 alkyl optionally substituted by 1 to 6 halogen atoms, C1-4 alkoxy optionally substituted by 1 to 6 halogen atoms;  cyano;  nitro;  OnS(O)n,R12 ;  NR13 R14 ;  (C1-4 alkyl) carbonyl;  or (C1-4 alkoxy)carbonyl; R8 is hydrogen or a salt forming moiety; R12 is C1-4 alkyl optionally substituted by 1 to 6 halogen atoms; each of R13 and R14 is, independently, hydrogen or C1-4 alkyl; n is zero or one;  and n' is zero, one or two. 34. A compound according to claim 33 wherein each of R1, R2, R9 and R10 is, independently, hydrogen or methyl;  and R5 is chlorine, bromine, methyl, methoxy, nitro, trifluoromethyl or methyl sulfonyl. 35. A compound according to claim 34 wherein each R6 and R7 is independently hydrogen;  chlorine;  fluorine;  bromine;  methyl;  C1-4 alkoxy;  trifluoromethoxy;  cyano;  nitro;  trifluoromethyl;  OnS(O)n,R12, wherein n is zero, n' is 0 or 2 and R12 is methyl, chloromethyl, trifluoromethyl;  ethyl or n-propyl, (C1-4 alkyl)carbonyl and R6 is in the 3-position and R7 is in the 4-position. 36. A compound according to claim 34 wherein R6 is hydrogen and R7 is hydrogen, chlorine, bromine, fluorine, cyano, trifluoromethyl or OnS(O)n,R12 wherein n is zero, n' is 2 and R12 is C1-4 alkyl optionally substituted by 1 to 6 halogen atoms. 37. The method of controlling undesirable vegetation comprising applying to the area where control is desired, an herbicidally effective amount of a compound according to claim 2 wherein Ar represents the group  (Chemical Structure image '18' not included in text)   X is CH2 CH2 ;  q is zero; each of R1, R2, R9 and R10 is, independently, hydrogen or C1-4 alkyl; R5 is halogen;  C1-4 alkyl optionally substituted by 1 to 6 halogen atoms;  C1-4 alkoxy optionally substituted by 1 to 6 halogen atoms;  nitro;  cyano;  or OnS(O)n,R12 ; each of R6 and R7 is independently hydrogen;  halogen;  C1-4 alkyl optionally substituted by 1 to 6 halogen atoms;  C1-4 alkoxy optionally substituted by 1 to 6 halogen atoms;  cyano;  nitro;  OnS(O)n,R12 ;  NR13 R14 ;  (C1-4 alkyl) carbonyl;  or (C1-4 alkoxy)carbonyl; R8 is hydrogen or a salt forming moiety; R12 is C1-4 alkyl optionally substituted by 1 to 6 halogen atoms; each of R13 and R14 is, independently, hydrogen or C1-4 alkyl; n is zero or one;  and n' is zero, one or two. 38. The method according to claim 37 wherein each of R1, R2, R9 and R10 is, independently, hydrogen or methyl;  and R5 is chlorine, bromine, methyl, methoxy, nitro, trifluoromethyl or methyl sulfonyl. 39. The method according to claim 38 wherein each R6 and R7 is independently hydrogen;  chlorine;  fluorine;  bromine;  methyl;  C1-4 alkoxy;  trifluoromethoxy;  cyano;  nitro;  trifluoromethyl;  OnS(O)n,R12 wherein n is zero, n' is 0 or 2 and R12 is methyl, chloromethyl, trifluoromethyl;  ethyl or n-propyl, (C1-4 alkyl)carbonyl and R6 is in the 3-position and R7 is in the 4-position. 40. The method according to claim 38 wherein R6 is hydrogen and R7 is hydrogen, chlorine, bromine, fluorine, cyano, trifluoromethyl or OnS(O)n,R12 wherein n is zero, n' is 2 and R12 is C1-4 alkyl optionally substituted by 1 to 6 halogen atoms. 41. The herbicidal composition of claim 24 wherein Ar represents the group  (Chemical Structure image '19' not included in text)   X is CH2 CH2 ;  q is zero; each of R1, R2, R9 and R10 is, independently, hydrogen or C1-4 alkyl; R5 is halogen;  C1-4 alkyl optionally substituted by 1 to 6 halogen atoms;  C1-4 alkoxy optionally substituted by 1 to 6 halogen atoms;  nitro;  cyano;  OnS(O)n R12 ; each of R6 and R7 is independently hydrogen;  halogen;  C1-4 alkyl optionally substituted by 1 to 6 halogen atoms, C1-4 alkoxy optionally substituted by 1 to 6 halogen atoms;  cyano;  nitro;  OnS(O)n,R12 ;  NR13 R14 ;  (C1-4 alkyl) carbonyl;  or (C1-4 alkoxy)carbonyl; R8 is hydrogen or a salt forming moiety; R12 is C1-4 alkyl optionally substituted by 1 to 6 halogen atoms; each of R13 and R14 is, independently, hydrogen or C1-4 alkyl; n is zero or one;  and n' is zero, one or two. 42. The herbicidal composition of claim 41 wherein each of R1, R2, R9 and R10 is, independently, hydrogen or methyl;  and R5 is chlorine, bromine, methyl, methoxy, nitro, trifluoromethyl or methyl sulfonyl. 43. The herbicidal composition of claim 42 wherein each R6 and R7 is independently hydrogen;  chlorine;  fluorine;  bromine;  methyl;  C1-4 alkoxy;  trifluoromethoxy;  cyano;  nitro;  trifluoromethyl;  OnS(O)n,R12, wherein n is zero, n' is 0 or 2 and R12 is methyl, chloromethyl, trifluoromethyl;  ethyl or n-propyl, (C1-4 alkyl)carbonyl and R6 is in the 3-position and R7 is in the 4-position. 44. The herbicidal composition of claim 43 wherein R6 is hydrogen and R7 is hydrogen, chlorine, bromine, fluorine, cyano, trifluoromethyl or OnS(O)n,R12 wherein n is zero, n' is 2 and R12 is C1-4 alkyl optionally substituted by 1 to 6 halogen atoms.
法律状态
(US5801120) LEGAL DETAILS FOR US5801120  Actual or expected expiration date=2002-10-02    Legal state=DEAD    Status=LAPSED     Event publication date=1989-09-22  Event code=US/APP  Event indicator=Pos  Event type=Examination events  Application details  Application country=US US07411086  Application date=1989-09-22  Standardized application number=1989US-07411086     Event publication date=1989-09-22  Event code=US/EXMR  Event type=Administrative notifications  USPTO Examiner Name Primary Examiner: REAMER, JAMES H    Event publication date=1989-09-22  Event code=US/ART  Event type=Administrative notifications  USPTO Art Group  ART=1614     Event publication date=1989-09-22  Event code=US/DK  Event type=Examination events  Attorney Docket Number Docket Nbr: Z658CIP    Event publication date=1989-09-22  Event code=US/ENT  Event type=Administrative notifications  Entity Status Set to Undiscounted Business Entity Status: UNDISCOUNTED    Event publication date=1989-09-22  Event code=US/AIA  Event type=Administrative notifications  First Inventor File Indicated:  AIA=No     Event publication date=1989-10-10  Event code=US/INCD  Event type=Examination events  Event type=OAO  Notice Mailed--Application Incomplete--Filing Date Assigned    Event publication date=1990-01-09  Event code=US/DOCK  Event indicator=Pos  Event type=Examination events  Case Docketed to Examiner    Event publication date=1990-02-07  Event code=US/RESTREQ  Event type=Examination events  Event type=Corrections  Event type=OAO  Restriction/Election Requirement    Event publication date=1990-05-29  Event code=US/IDS  Event type=Examination events  Event type=OAI  Information Disclosure Statement Filed    Event publication date=1990-05-29  Event code=US/ELC  Event type=Examination events  Event type=OAI  Response to Election / Restriction Filed    Event publication date=1990-05-29  Event code=US/136G  Event type=OAO  Request for Extension of Time - Granted    Event publication date=1990-08-21  Event code=US/CTMS  Event type=Examination events  Event type=OAO  Miscellaneous Action with SSP    Event publication date=1990-09-25  Event code=US/CTNFR  Event type=Examination events  Event type=OAI  Response after Non-Final Action    Event publication date=1991-03-27  Event code=US/CTMS  Event type=Examination events  Event type=OAO  Miscellaneous Action with SSP    Event publication date=1991-09-23  Event code=US/IDS  Event type=Examination events  Event type=OAI  Information Disclosure Statement Filed    Event publication date=1991-09-23  Event code=US/CTNFR  Event type=Examination events  Event type=OAI  Response after Non-Final Action    Event publication date=1991-09-23  Event code=US/136G  Event type=OAO  Request for Extension of Time - Granted    Event publication date=1991-12-11  Event code=US/CTNF  Event type=Examination events  Event type=OA  Event type=OAO  Non-Final Rejection    Event publication date=1992-04-07  Event code=US/ID  Event indicator=Neg  Event type=Opposition and reexamination events  Declaration of Interference    Event publication date=1993-09-29  Event code=US/IDF  Event indicator=Pos  Event type=Opposition and reexamination events  Interference Decision on Priority - Favorable    Event publication date=1995-04-03  Event code=US/CTNFR  Event type=Examination events  Event type=OAI  Response after Non-Final Action    Event publication date=1995-05-23  Event code=US/CTNF  Event type=Examination events  Event type=OA  Event type=OAO  Non-Final Rejection    Event publication date=1995-10-27  Event code=US/CTNFR  Event type=Examination events  Event type=OAI  Response after Non-Final Action    Event publication date=1996-02-20  Event code=US/CTNF  Event type=Examination events  Event type=OA  Event type=OAO  Non-Final Rejection    Event publication date=1996-05-14  Event code=US/CTNFR  Event type=Examination events  Event type=OAI  Response after Non-Final Action    Event publication date=1996-08-01  Event code=US/CTFR  Event type=Examination events  Event type=OA  Event type=OAO  Final Rejection    Event publication date=1996-11-05  Event code=US/NOAPLF  Event type=APL  Notice of Appeal Filed    Event publication date=1996-12-23  Event code=US/AS  Event type=Change of name or address  Event type=Reassignment  Assignment ASSIGNMENT OF ASSIGNORS INTEREST ASSIGNORS:LEE, SHY-FUH NISHIZAKA, TAKASHI KOMATSUBARA, KENICHI REEL/FRAME:008277/0970 SIGNING DATES FROM 19961105 TO 19961203     Event publication date=1997-03-05  Event code=US/ABNEA  Event indicator=Neg  Event type=Event indicating Not In Force  Event type=OAI  Expressly Abandoned -- During Examination    Event publication date=1997-03-05  Event code=US/136G  Event type=OAO  Request for Extension of Time - Granted    Event publication date=1997-06-03  Event code=US/NOAM  Event indicator=Pos  Event type=Examination events  Event type=OAO  Mail Notice of Allowance    Event publication date=1997-11-21  Event code=US/ISSM  Event indicator=Pos  Event type=Examination events  Event type=OAO  Event type=Restitution or restoration  Issue Notification Mailed    Event publication date=1998-07-27  Event code=US/ISSM  Event indicator=Pos  Event type=Examination events  Event type=OAO  Event type=Restitution or restoration  Issue Notification Mailed    Event publication date=1998-09-01  Event code=US/A  Event indicator=Pos  Event type=Event indicating In Force  Patents Granted before 2001-04-15  Publication country=US  Publication number=US5801120  Publication stage Code=A  Publication date=1998-09-01  Standardized publication number=US5801120     Event publication date=2001-09-11  Event code=US/NMFP  Event type=Payment or non-payment notifications  Publication of First Notice of Maintenance Fees Payable. PAYMENT NOTICE YEAR:  Year of payment of annual fees=3     Event publication date=2002-03-19  Event code=US/REMI  Event type=Administrative notifications  Maintenance fee reminder mailed    Event publication date=2002-09-01  Event code=US/FP  Event indicator=Neg  Event type=Event indicating Not In Force  Event type=Payment or non-payment notifications  Expired due to failure to pay maintenance fee  Effective date of the event=2002-09-01     Event publication date=2002-09-03  Event code=US/LAPS  Event indicator=Neg  Event type=Event indicating Not In Force  Event type=Payment or non-payment notifications  Lapse for failure to pay maintenance fees    Event publication date=2002-10-02  Event code=US/FP  Event indicator=Neg  Event type=Event indicating Not In Force  Event type=Payment or non-payment notifications  Expired due to failure to pay maintenance fee    Event publication date=2002-10-02  Event code=US/EXP  Event indicator=Neg  Event type=Event indicating Not In Force  Patent expired    Event publication date=2005-09-13  Event code=US/NMFP  Event type=Payment or non-payment notifications  Publication of First Notice of Maintenance Fees Payable. PAYMENT NOTICE YEAR:  Year of payment of annual fees=7     Event publication date=2009-09-15  Event code=US/NMFP  Event type=Payment or non-payment notifications  Publication of First Notice of Maintenance Fees Payable. PAYMENT NOTICE YEAR:  Year of payment of annual fees=11
专利类型码
A
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