KR920018032A - 벤젠술포닐우레아 유도체 - Google Patents
벤젠술포닐우레아 유도체 Download PDFInfo
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- KR920018032A KR920018032A KR1019910003704A KR910003704A KR920018032A KR 920018032 A KR920018032 A KR 920018032A KR 1019910003704 A KR1019910003704 A KR 1019910003704A KR 910003704 A KR910003704 A KR 910003704A KR 920018032 A KR920018032 A KR 920018032A
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- compound
- general formula
- alkyl
- benzenesulfonamide
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- GHDLZGOOOLEJKI-UHFFFAOYSA-N benzenesulfonylurea Chemical class NC(=O)NS(=O)(=O)C1=CC=CC=C1 GHDLZGOOOLEJKI-UHFFFAOYSA-N 0.000 title claims 5
- 150000001875 compounds Chemical class 0.000 claims 29
- -1 C 1 -C 3 alkoxy Chemical group 0.000 claims 7
- 125000000217 alkyl group Chemical group 0.000 claims 7
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 7
- 229910052799 carbon Inorganic materials 0.000 claims 5
- 229910052739 hydrogen Inorganic materials 0.000 claims 5
- 125000003545 alkoxy group Chemical group 0.000 claims 4
- 229910052736 halogen Inorganic materials 0.000 claims 4
- 150000002367 halogens Chemical class 0.000 claims 4
- 229910052760 oxygen Inorganic materials 0.000 claims 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 4
- KHBQMWCZKVMBLN-IDEBNGHGSA-N benzenesulfonamide Chemical group NS(=O)(=O)[13C]1=[13CH][13CH]=[13CH][13CH]=[13CH]1 KHBQMWCZKVMBLN-IDEBNGHGSA-N 0.000 claims 3
- 125000004438 haloalkoxy group Chemical group 0.000 claims 3
- 239000000203 mixture Substances 0.000 claims 3
- 229910052717 sulfur Inorganic materials 0.000 claims 3
- 125000006559 (C1-C3) alkylamino group Chemical group 0.000 claims 2
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims 2
- 239000004480 active ingredient Substances 0.000 claims 2
- 229910052794 bromium Inorganic materials 0.000 claims 2
- 229910052801 chlorine Inorganic materials 0.000 claims 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 2
- 229910052731 fluorine Inorganic materials 0.000 claims 2
- 230000002363 herbicidal effect Effects 0.000 claims 2
- 229910052740 iodine Inorganic materials 0.000 claims 2
- 125000006677 (C1-C3) haloalkoxy group Chemical group 0.000 claims 1
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims 1
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims 1
- OYXIWFKYYOGTLP-UHFFFAOYSA-N 1-[2-(2-fluoro-1-hydroxypropyl)phenyl]sulfonyl-3-(4-methoxy-6-methylpyrimidin-2-yl)urea Chemical compound COC1=CC(C)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)C(O)C(C)F)=N1 OYXIWFKYYOGTLP-UHFFFAOYSA-N 0.000 claims 1
- XRMDCWJNPDVAFI-UHFFFAOYSA-N 2,2,6,6-tetramethyl-1-oxopiperidin-1-ium-4-ol Chemical compound CC1(C)CC(O)CC(C)(C)[N+]1=O XRMDCWJNPDVAFI-UHFFFAOYSA-N 0.000 claims 1
- BPMDVTSQTBAEOV-UHFFFAOYSA-N 2-(1-chloro-3-oxobutan-2-yl)benzenesulfonamide Chemical compound CC(=O)C(CCl)C1=CC=CC=C1S(N)(=O)=O BPMDVTSQTBAEOV-UHFFFAOYSA-N 0.000 claims 1
- HEOIJEJJYPHDDK-UHFFFAOYSA-N 2-(1-fluoro-3-oxobutan-2-yl)benzenesulfonamide Chemical compound CC(=O)C(CF)C1=CC=CC=C1S(N)(=O)=O HEOIJEJJYPHDDK-UHFFFAOYSA-N 0.000 claims 1
- HIYQMFBHZJDKBE-UHFFFAOYSA-N 2-(1-fluoro-4-oxopentan-3-yl)benzenesulfonamide Chemical compound FCCC(C(=O)C)C1=CC=CC=C1S(N)(=O)=O HIYQMFBHZJDKBE-UHFFFAOYSA-N 0.000 claims 1
- OQQZQUKTXPOOJF-UHFFFAOYSA-N 2-(2-fluoro-4-oxopentan-3-yl)benzenesulfonamide Chemical compound CC(F)C(C(C)=O)C1=CC=CC=C1S(N)(=O)=O OQQZQUKTXPOOJF-UHFFFAOYSA-N 0.000 claims 1
- 206010011703 Cyanosis Diseases 0.000 claims 1
- 241000196324 Embryophyta Species 0.000 claims 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 239000003513 alkali Substances 0.000 claims 1
- 125000004414 alkyl thio group Chemical group 0.000 claims 1
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 125000004093 cyano group Chemical group *C#N 0.000 claims 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 1
- 125000001188 haloalkyl group Chemical group 0.000 claims 1
- 239000004009 herbicide Substances 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- 239000000575 pesticide Substances 0.000 claims 1
- 125000006239 protecting group Chemical group 0.000 claims 1
- 230000001172 regenerating effect Effects 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 238000005507 spraying Methods 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D521/00—Heterocyclic compounds containing unspecified hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
- A01N47/36—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the group >N—CO—N< directly attached to at least one heterocyclic ring; Thio analogues thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/22—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound oxygen atoms
- C07C311/29—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound oxygen atoms having the sulfur atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Agronomy & Crop Science (AREA)
- General Health & Medical Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Abstract
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Description
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Claims (25)
- 다음 일반식(Ⅰ)로 표시도는 벤젠 술포닐 우레아 유도체.상기식에서 R1은 H, C1-C3할로알킬, 할로겐, CN, 니트로, C1-C3알콕시, C1-C3할로알콕시, SO2NRⅠRⅡ, C1-C3알칼치오, C1-C3알킬술피닐, C1-C3알킬술포닐, SCHF2, NH2, NH2CH2N(Me)2, C1-C2알킬로서, C1-C|2알콕시, C1-C2할로알콕시, SH, SCH3, CN 또는 OH로 치환된 것; 또는 CO2RⅢ; 여기서 RⅠ은 H, C1-C4알킬, C|2-C3시아노알킬, 메톡시, 또는 에톡시; RⅡ은 H, C1-C4알킬, C3-C4알케닐,; 또는 RⅠ과 RⅡ가 동시에 연결되어, -(CH2)3-, -(CH2)4)-, -(CH2)5)-, -CH|2CH2OCH2CH2-인 것, RⅢ은 C1-C|4알킬, C3-C4알케닐, C3-C4알키닐, C1-C4알킬포서 할로겐, 시아노가 1~3개 치환된것, C5-C6싸이클로알킬, C4-C7싸이클로알킬 또는 C2-C4알콕시, R2는 C|1-C6알킬로써, 1~3개의 하로겐이 치환된것, R3는 H 또는 CH3, W는 O 또는 S, A는 A1, A2, A3, A4, A5, A6, 또는 A7 로서 아래와 같다.여기서, X는 C1-C4알킬, C1-C4알콕시, C1-C|4할로알콕시, C1-C4할로알킬, C1-C4할로알킬치오, C1-C4알킬치오, 히로겐, C2-C5알콕시알킬, C|2-C5알콕시알콕시, 아미노, C1-C3알킬아미노, 디(C1-C3알킬)아미노, 또는 C3-C5의 싸이클로알킬, Y는 H, C1-C4알킬, C1-C4알콕시, C1-C4할로알콕시, C|1-C4할로알킬치오, C1-C4알킬치오, C2-C5알콕시알킬, C2-C5알콕시알콕시, 아미노, C1-C3알킬아미노, 디(C|1-C3알킬)아미노, C3-C4알케닐옥시, C3-C4알키닐옥시, C2-C5알킬치오알킬, C1-C4할로알킬, C2-C4알키닐, 아지도, 시나오, C2-C5알킬술피닐알킬, C2-C5알킬술포닐알킬, CH|2OH, C3-C5싸이클로알킬, C3-C5싸이클로알콕시,m은 2 또는 3, L1과 L2는 독립적으로 O 또는 S, R4과 R5는 독립적으로 C1-C2알킬, R6는 H 또는 CH3, Z는 CH, N, CCH 또는 CC2H5, Y|1는 O 또는 CH2, X'는 CH3, OCH3, OC2H5, 또는 OCHF2, Y2는 CH3CH|2CH3, OCH3, OCH2CH3, SCH3또는 SCH|2CH3, X2는 CH3CH2CH3, 또는 CH2CF3, Y3는 H 또는 CH3, X3는 CH3, 또는 OCH3, Y4는 CH3, OCH3, OC2H5,CH2OCH3, 또는 Cl, X4는 CH3, OCH3, OC2H5,CH2OCH3, 또는 Cl, 그리고 그들의 농업적으로 적절한 염을 말한다. 단 (1) X가 Cl, Br, F, I이면, Z는 CH이고 Y는 OCH3, OC2H5, NCH3(OCH3), NH3, NHCH3N(CH|3)3, 또는 OCHF2,이다. (2) X 또는 Y가 OCHF2,이면 Z는 CH이다. (3)X4와 Y4가 동시에 Cl은 아니다. (4)W가 S이면, R3는 H,A,는 A1이고, Z는 CH 또는 N이고, Y는 CH3, OCH3, OCH2CH3,CH2OCH3, C2H5, CF3, SCH3, OCH2CH≡CH|2,OCH2C≡CH,OCH2CH2OCH3CH(OCH3)2또는이다. (5) X와 Y의 합친 탄소원자 총수가 4이상이면 R2의 탄소수는 4이거나 그 이하이다.
- 제 1 항에 있어서, W는 O, R3는 H인 화합물.
- 제 1 항에 있어서, R1는 할로겐, C1-C2알킬, C1-C2알콕시, C1-C2할로알킬, C1-C2알킬치오 또는 할로알콕시, CH2CN 중에서 선택되노; X는 C1-C2알킬, C1-C2알콕시, Cl, Br, F, I, OCHF2, OCH2CH2F, OCH2CHF2, OCH|2CF3, CH2Cl 또는 CH2Br중에서 선택되고; Y는 C1-C2알킬, C1-C2알콕시, CH2OCH3,CH2OCH2CH3,NHCH3, N(OCH3)CH3, N(CH3)2, CF3, SCH3, OCH2CH≡CH2,OCH2C≡CH,OCH2CH2OCH2, CH2SCH3,OCHF2, OCF2Br, SCHF2, 싸이클로프로필, C≡CH 또는 C≡C-CH이고, R|4, R5는 C1-C2알킬이고, R6는 H 또는 CH3이고; L1, L|2는 O 또는 S, m은 2 또는 3인 화합물.
- 제 1 항에 있어서, A는 A1, Z는 CH이고, X는 CH3, C2H5, OCH|3, OCH2CH3, Cl 또는 OCHF2,이고, Y는 CH3,OCH3, OC2H5, C|2H5, CH2OCH3, CH(OCH3)2또는 싸이클로프로필인 화합물.
- 제 1 항에 있어서, R2는 CH2F, CH2CH2F, CHFCH3, CH2Cl, CH2Br, CHCl2, CHFCl, CH2CH2Cl, CHClCH3, CHF2, CHClCH2Cl, CHFCH|2F 또는 CH2CHF2,인 화합물.
- 제 1 항에 있어서, 상기 일반식(Ⅰ)은 2-(1-히드록시-2-플루오로메틸)-N-[(4,6-디메톨시피리미딘-2-일)아미노카보닐]-벤젠술폰아미드인 화합물.
- 제 1 항에 있어서, 상기 일반식(Ⅰ)은 2-(1-히드록시-2-플루오로메틸)-N-[(4-메톨시-6-메틸피리미딘-2-일)아미노카보닐]-벤젠술폰아미드인 화합물.
- 제 1 항에 있어서, 상기 일반식(Ⅰ)은 2-(1-히드록시-2-플루오로메틸)-N-[(4,6-디메킬피리미딘-2-일)아미노카보닐]-벤젠술폰아미드인 화합물.
- 제 1 항에 있어서, 상기 일반식(Ⅰ)은 2-(1-히드록시-2-플루오로프로필)-N-[(4,6-디메톨시피리미딘-2-일)아미노카보닐]-벤젠술폰아미드인 화합물.
- 제 1 항에 있어서, 상기 일반식(Ⅰ)은 2-(1-히드록시-2-플루오로프로필)-N-[(4-메톡시-6-메틸피리미딘-2-일)아미노카보닐]-벤젠술폰아미드인 화합물.
- 제 1 항에 있어서, 상기 일반식(Ⅰ)은 2-(1-히드록시-2-플루오로프로필)-N-[(4,6-디메톨시피리미딘-2-일)아미노카보닐]-벤젠술폰아미드인 화합물.
- 제 1 항에 있어서, 상기 일반식(Ⅰ)은 2-(1-히드록시-2-클로로에틸)-N-[(4,6-디메톨시피리미딘-2-일)아미노카보닐]-벤젠술폰아미드인 화합물.
- 제 1 항에 있어서, 상기 일반식(Ⅰ)은 2-(1-히드록시-2-클로로에틸)-N-[(4-메톡시-6-메틸피리미딘-2-일)아미노카보닐]-벤젠술폰아미드인 화합물.
- 제 1 항에 있어서, 상기 일반식(Ⅰ)은 2-(1-히드록시-2-클로로에틸)-N-[(4,6-디메톨시피리미딘-2-일)아미노카보닐]-벤젠술폰아미드인 화합물.
- 다음 일반식(Ⅱ)로 표시되는 상기 일반식(Ⅰ)의 중간체화합물.여기서, R1, R2, R3, W 및 A는 제 1 항에서 정의한 바와 같다.
- 제 15 항에 있어서, R1은 H, R2은 CH2F, CHF2, CH2Cl, CHFCH3, CH2,CH2F, R3은 H, W는 O, A는 A1인 화합물.
- 다음 일반식(Ⅳ)로 표시되는 상기 일반식(Ⅰ)의 중간체화합물.여기서, R1, R2, 는 제 1 항에의 정의와 같고, Ac는 아세틸 및 산, 알칼리 또는 그외의 조건하에서 히드록시기를 재새성시킬수 있는 보호기를 나타낸다.
- 제 17 항에 있어서, R1은 H, R2은 CH2F, CH2Cl, CHFCH|3, CH2CHF,CHClCH3, CHF2,인 화합물.
- 제 17 항에 있어서, 상기 일반식(Ⅳ)의 화합물은 2-(1-아세틸-2-플루오로에틸)-벤젠술폰아미드인 화합물.
- 제 17 항에 있어서, 상기 일반식(Ⅳ)의 화합물은 2-(1-아세틸-2-플루오로프로필)-벤젠술폰아미드인 화합물.
- 제 17 항에 있어서, 상기 일반식(Ⅳ)의 화합물은 2-(1-아세틸-3-플루오로프로필)-벤젠술폰아미드인 화합물.
- 제 17 항에 있어서, 상기 일반식(Ⅳ)의 화합물은 2-(1-아세틸-2-클로로에틸)-벤젠술폰아미드인 화합물.
- 다음 일반식(Ⅰ)로 표시되는 벤젠술포닐우레아 유도체중 적어도 어느 하나의 화합물을 유효성분으로 함유하는 제초제 조성물.상기 식에서, R1, R2, R3, w, A는 각각 상기 정의한 바와 같다.
- 다음 일반식 (Ⅰ)로 표시되는 벤젠술포닐우레아 유도체중 적어도 어느 하나의 화합물의 유효량을 살포하여 잡초를 제거하는 방법.상기 식에서, R1, R2, R3, w, A는 각각 상기 정의한 바와 같다.
- 다음 일반식 (Ⅰ)로 표시되는 벤젠술포닐우레아 유도체중 적어도 어느 하나를 유효성분으로 하는 화합물과 이와 혼합하여 사용할수 있는 농약으로 구성된 제초제 혼합조성물.상기 식에서, R1, R2, R3, w, A는 각각 상기 정의한 바와 같다.※ 참고사항 : 최초출원 내용에 의하여 공개되는 것임.
Priority Applications (9)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR1019910003704A KR930009825B1 (ko) | 1991-03-08 | 1991-03-08 | 벤젠술포닐우레아 유도체 |
| PCT/KR1992/000007 WO1992015568A1 (en) | 1991-03-08 | 1992-03-09 | Benzenesulfonylurea derivatives |
| CA002107235A CA2107235C (en) | 1991-03-08 | 1992-03-09 | Benzenesulfonylurea derivatives |
| BR9205739A BR9205739A (pt) | 1991-03-08 | 1992-03-09 | Composto, composto intermediáro, herbicida, método para controlar ervas daninhas, e, composições herbicidas. |
| JP4505613A JP2656383B2 (ja) | 1991-03-08 | 1992-03-09 | ベンゼンスルホニル尿素誘導体 |
| EP92905709A EP0575378A1 (en) | 1991-03-08 | 1992-03-09 | Benzenesulfonylurea derivatives |
| AU13514/92A AU665942B2 (en) | 1991-03-08 | 1992-03-09 | Benzenesulfonylurea derivatives |
| US08/117,076 US5461025A (en) | 1991-03-08 | 1992-03-09 | Benzenesulfonylurea derivatives |
| US08/477,737 US5736628A (en) | 1991-03-08 | 1995-06-07 | Benzenesulfonylurea derivatives |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR1019910003704A KR930009825B1 (ko) | 1991-03-08 | 1991-03-08 | 벤젠술포닐우레아 유도체 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR920018032A true KR920018032A (ko) | 1992-10-21 |
| KR930009825B1 KR930009825B1 (ko) | 1993-10-11 |
Family
ID=19311878
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019910003704A KR930009825B1 (ko) | 1991-03-08 | 1991-03-08 | 벤젠술포닐우레아 유도체 |
Country Status (8)
| Country | Link |
|---|---|
| US (2) | US5461025A (ko) |
| EP (1) | EP0575378A1 (ko) |
| JP (1) | JP2656383B2 (ko) |
| KR (1) | KR930009825B1 (ko) |
| AU (1) | AU665942B2 (ko) |
| BR (1) | BR9205739A (ko) |
| CA (1) | CA2107235C (ko) |
| WO (1) | WO1992015568A1 (ko) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2203011C (en) * | 1994-10-24 | 2001-12-11 | Korea Research Institute Of Chemical Technology | Herbicidal sulfonyl urea derivatives |
| WO1997031913A1 (en) * | 1996-02-27 | 1997-09-04 | Korea Research Institute Of Chemical Technology | Herbicidal sulfonamide derivatives |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ZA814658B (en) * | 1980-07-11 | 1983-02-23 | Du Pont | Herbicidal sulfonamides |
| EP0125205A1 (de) * | 1983-04-13 | 1984-11-14 | Ciba-Geigy Ag | N-Phenylsulfonyl-N'-pyrimidinyl- und -triazinylharnstoffe |
| JPS6216457A (ja) * | 1985-06-12 | 1987-01-24 | イ−・アイ・デユポン・デ・ニモアス・アンド・カンパニ− | 除草剤性スルホンアミド類 |
-
1991
- 1991-03-08 KR KR1019910003704A patent/KR930009825B1/ko not_active IP Right Cessation
-
1992
- 1992-03-09 EP EP92905709A patent/EP0575378A1/en not_active Withdrawn
- 1992-03-09 JP JP4505613A patent/JP2656383B2/ja not_active Expired - Fee Related
- 1992-03-09 AU AU13514/92A patent/AU665942B2/en not_active Ceased
- 1992-03-09 CA CA002107235A patent/CA2107235C/en not_active Expired - Fee Related
- 1992-03-09 US US08/117,076 patent/US5461025A/en not_active Expired - Fee Related
- 1992-03-09 WO PCT/KR1992/000007 patent/WO1992015568A1/en not_active Application Discontinuation
- 1992-03-09 BR BR9205739A patent/BR9205739A/pt not_active Application Discontinuation
-
1995
- 1995-06-07 US US08/477,737 patent/US5736628A/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| BR9205739A (pt) | 1994-11-08 |
| JPH06505254A (ja) | 1994-06-16 |
| CA2107235A1 (en) | 1992-09-09 |
| CA2107235C (en) | 1997-11-04 |
| EP0575378A1 (en) | 1993-12-29 |
| AU1351492A (en) | 1992-10-06 |
| US5736628A (en) | 1998-04-07 |
| JP2656383B2 (ja) | 1997-09-24 |
| US5461025A (en) | 1995-10-24 |
| WO1992015568A1 (en) | 1992-09-17 |
| KR930009825B1 (ko) | 1993-10-11 |
| AU665942B2 (en) | 1996-01-25 |
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