KR830002698A - 제초제 및 화학중간체 제조방법 - Google Patents
제초제 및 화학중간체 제조방법 Download PDFInfo
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- KR830002698A KR830002698A KR1019800001833A KR800001833A KR830002698A KR 830002698 A KR830002698 A KR 830002698A KR 1019800001833 A KR1019800001833 A KR 1019800001833A KR 800001833 A KR800001833 A KR 800001833A KR 830002698 A KR830002698 A KR 830002698A
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- 239000004009 herbicide Substances 0.000 title claims 2
- 239000000126 substance Substances 0.000 title claims 2
- 239000000543 intermediate Substances 0.000 title 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 32
- 239000001257 hydrogen Substances 0.000 claims 32
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 25
- 239000000460 chlorine Substances 0.000 claims 23
- 229910052801 chlorine Inorganic materials 0.000 claims 20
- 150000001875 compounds Chemical class 0.000 claims 14
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 13
- -1 2 Chemical class 0.000 claims 12
- 125000000217 alkyl group Chemical group 0.000 claims 11
- 125000004093 cyano group Chemical group *C#N 0.000 claims 10
- 125000004432 carbon atom Chemical group C* 0.000 claims 9
- 125000001309 chloro group Chemical group Cl* 0.000 claims 9
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 7
- 229910052736 halogen Inorganic materials 0.000 claims 6
- 150000002367 halogens Chemical class 0.000 claims 6
- 150000002431 hydrogen Chemical class 0.000 claims 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 5
- 238000004519 manufacturing process Methods 0.000 claims 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 3
- 230000002363 herbicidal effect Effects 0.000 claims 3
- 238000000034 method Methods 0.000 claims 3
- KXKVLQRXCPHEJC-UHFFFAOYSA-N methyl acetate Chemical compound COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 claims 3
- 150000003839 salts Chemical class 0.000 claims 3
- 241000196324 Embryophyta Species 0.000 claims 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Substances CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims 2
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 125000003277 amino group Chemical group 0.000 claims 1
- 150000003863 ammonium salts Chemical class 0.000 claims 1
- 150000007942 carboxylates Chemical class 0.000 claims 1
- DOBRDRYODQBAMW-UHFFFAOYSA-N copper(i) cyanide Chemical compound [Cu+].N#[C-] DOBRDRYODQBAMW-UHFFFAOYSA-N 0.000 claims 1
- 238000006193 diazotization reaction Methods 0.000 claims 1
- 230000026030 halogenation Effects 0.000 claims 1
- 238000005658 halogenation reaction Methods 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 150000002500 ions Chemical class 0.000 claims 1
- 238000006396 nitration reaction Methods 0.000 claims 1
- 150000002923 oximes Chemical class 0.000 claims 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 claims 1
- 229910001414 potassium ion Inorganic materials 0.000 claims 1
- 229910001415 sodium ion Inorganic materials 0.000 claims 1
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- C07C249/00—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C249/04—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton of oximes
- C07C249/12—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton of oximes by reactions not involving the formation of oxyimino groups
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
- C07C49/84—Ketones containing a keto group bound to a six-membered aromatic ring containing ether groups, groups, groups, or groups
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- 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
- A01N35/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical
- A01N35/04—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical containing aldehyde or keto groups, or thio analogues thereof, directly attached to an aromatic ring system, e.g. acetophenone; Derivatives thereof, e.g. acetals
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- 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
- A01N35/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical
- A01N35/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical at least one of the bonds to hetero atoms is to nitrogen
- A01N35/10—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical at least one of the bonds to hetero atoms is to nitrogen containing a carbon-to-nitrogen double bond
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- 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
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/36—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids
- A01N37/38—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids having at least one oxygen or sulfur atom attached to an aromatic ring system
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- 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
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/44—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids
- A01N37/50—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids the nitrogen atom being doubly bound to the carbon skeleton
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/44—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by —CHO groups
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/45—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by at least one doubly—bound oxygen atom, not being part of a —CHO group
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C251/32—Oximes
- C07C251/50—Oximes having oxygen atoms of oxyimino groups bound to carbon atoms of substituted hydrocarbon radicals
- C07C251/60—Oximes having oxygen atoms of oxyimino groups bound to carbon atoms of substituted hydrocarbon radicals of hydrocarbon radicals substituted by carboxyl groups
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/48—Preparation of compounds having groups
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/51—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition
- C07C45/511—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of singly bound oxygen functional groups to >C = O groups
- C07C45/515—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of singly bound oxygen functional groups to >C = O groups the singly bound functional group being an acetalised, ketalised hemi-acetalised, or hemi-ketalised hydroxyl group
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- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
- C07C45/70—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction with functional groups containing oxygen only in singly bound form
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- C07C47/575—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings containing ether groups, groups, groups, or groups
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Abstract
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Claims (46)
- (1)화학식(Ⅲ)의 옥심과 화학식 X-CH2(R1)-CO-OR2(R2:알킬기)의 카르복실레이트와 반응시키며, 필요에 따라서는 화학식(Ⅰ)의 화합물(R2:알킬기)을 가수분해시켜 상응하는 화합물(R2:수소)로 전환시키던지, 필요에 따라서는 화학식(Ⅰ)의 화합물(R2:수소)과 가용성 이온 R2을 가지는 염기와 반응시켜 상응하는 염을 제조함을 특징으로 하는 화학실(Ⅰ)을 가지는 화합물 제조방법.
- 단, 화학식(Ⅰ)과 화학식(Ⅲ)에 있어서
- X : 니트로기 (-NO2), 할로겐 또는 시아노기(-CN),
- Y: 수소 또는 염소(Cl)
- Z: Y가 염소일때는 염소
- Y사 염소 또는 수소일때는 수소
- R: 수소 또는 탄수원자수가 3까지인 알킬기.
- R1: 수소 또는 메틸기
- R2: 수소, 탄소원자수가 10까지인 알킬기 또는 가용성 염이온.
- (2) 화학식(Ⅱ)의 화합물(X:수소)를 할로겐화반응 또는 니트로화반응시켜 화학식(Ⅱ)를 가지는 상응하는 화합물(X:할로겐 또는 니트로기)로 제조하여 필요에 따라서는 X를 시아노기로 하는 화합물로 제조하고 화학식(Ⅱ)의 화합물(X:니트로기)을 환원시켜 X를 아미노기로 하는 상응하는 화합물로 제조하여 CuCN으로 처리하여 디아조화반응을 시켜 화학식(Ⅱ)의 화합물을 제조하는 방법.
- 단, 화학식(Ⅱ)에 있어서,
- X: 니트로기(-NO2), 할로겐 또는 시아노기(-CN),
- Y: 수소 또는 염소
- Z: ① Y가 염소일때는 염소
- ② Y가 염소 또는 수소일 때는 수소
- R: 수소 또는 탄소원자수가 3까지인 알킬기.
- (3) 청구범위 (2)의 화학식(Ⅱ)을 가지는 화합물과 히드록실아민 또는 산부가염을 반응시킴을 특징으로하는 화학식(Ⅲ)의 화합물 제조방법.
- 단, 화학식(Ⅱ)는 청구범위 ②와 같고, 화학식(Ⅲ)에 있어서는
- X: 니트로기(-NO2), 할로겐 또는 시아노기(-CN0),
- Y: 수소 또는 염소
- Z: ① Y가 염소일때는 염소
- ② Y가 염소 또는 수소일 때는 수소
- R: 수소 또는 탄소원자수가 3까지인 알킬기.
- (4) 화학식(Ⅰ), (Ⅱ) 또는 (Ⅲ)을 가지는 최소한 한가지 화합물을 제초유효량 만큼 사용함을 특징으로한 제초 조성물.
- 단, 화학식(Ⅰ), (Ⅱ) 또는 (Ⅲ)에 있어서
- X : 니트로기 (-NO2), 할로겐 또는 시아노기(-CN),
- Y: 수소 또는 염소(Cl)
- Z: ① Y가 염소일때는 염소
- ② Y사 염소 또는 수소일때는 수소
- R: 수소 또는 탄수원자수가 3까지인 알킬기.
- R1: 수소 또는 메틸기
- R2: 수소, 탄소원자수가 10까지인 알킬기 또는 가용성 염이온.
- (5) 화학식(I)을 가지는 화합물을 제초유효량 사용하여 잡초에 접촉시킴을 특징으로 하는 잡초방제방법.
- 단, 화학식(Ⅰ)에 있어서
- X : 니트로기 (-NO2), 할로겐 또는 시아노기(-CN),
- Y: 수소 또는 염소(Cl)
- Z: ① Y가 염소일때는 염소
- ② Y사 염소 또는 수소일때는 수소
- R: 수소 또는 탄수원자수가 3까지인 알킬기.
- R1: 수소 또는 메틸기
- R2: 수소, 탄소원자수가 10까지인 알킬기 또는 가용성 염이온.
- (6) 화학식(I)에 있어서 R을 수소 또는 메틸기로 함을 특징으로 하는 청구범위 1-5항에 기재된 조성물 또는 그의 제조방법.
- (7) 화학식(I)에 있어서 R2를 수소, 탄소원자수가 4까지인 알킬기, 나트륨이온, 칼륨이온 또는 암모늄 이온으로 함을 특징으로 하는 청구범위 제 6항에 기재된 조성물 또는 그의 제조방법.
- (8) 화학식(I)에 있어서Z를 수소로 하고 Y를 클로로(-Cl )로 함을 특징으로 하는 청구범위 제 1-7항에 기재된 조성물 또는 그의 제조방법.
- (9) 화학식(I)을 가지는 화합물로서는 5-(2-클로로-4-트리플루오로메틸페녹시)-2-클로로벤즈알도옥심-0-(아세트산, 메틸에스테르), 5-(2-클로로-4-트리플루오로메틸페녹시)-2-클로로벤즈알도옥심-0-(2-프로피온산, 메틸에스테르), 5-(2-클로로-4-트리플루오로메틸페녹시)-2-클로로아세토페논옥심-0-(아세트산, 메틸에스테르), 5-(2-클로로-4-트리플루오로메틸페녹시)-2-클로로아세토페논옥심-0-(2-프로피온산, 메틸에스테르), 5-(2-클로로-4-트리플루오로메틸페녹시)-2-시아노벤즈알도옥심-0-(아세트산, 메틸에스테르), 5-(2-클로로-4-트리플루오로메틸페녹시)-2-시아노벤즈알도옥심-0-(2-프로피온산, 메틸에스레르), 5-(2-클로로-4-트리플루오로메틸페녹시)-2-시아노아세토페논옥심-0-(아세트산, 메틸에스레르), 5-(2-클로로-4-트리플루오로메틸페녹시)-2-시아노아세토페논옥심-0-(2-프로피온산, 메틸에스레르) 같은 것과 5-(2-클로로-4-트리플루오로메틸페녹시)-2-니트로아세토페논옥심-0-(2-프로피온산) 또는 5-(2-클로로-4-트리플루오로메틸페녹시)-2-니트로아세토페논옥심-o-아세토페논의 나트륨염 ; 칼륨염 또는 암모늄염 같은 가용성염의 형태를 특징으로 하는 청구범위 제 1-5항에 기재된 제조방법 또는 그의 조성물.
- ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US3804379A | 1979-05-11 | 1979-05-11 | |
US38043 | 1979-05-11 | ||
US136171 | 1980-04-15 | ||
US06/136,171 US4344789A (en) | 1979-05-11 | 1980-04-15 | Acids and esters of 5-(2-optionally substituted-4-trifluoromethyl-6-optionally substituted phenoxy)-2-nitro, -halo, or-cyano alpha substituted phenyl carboxy oximes, and method of controlling weeds with them |
Publications (2)
Publication Number | Publication Date |
---|---|
KR830002698A true KR830002698A (ko) | 1983-05-30 |
KR840001968B1 KR840001968B1 (ko) | 1984-10-26 |
Family
ID=26714792
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
KR1019800001833A KR840001968B1 (ko) | 1979-05-11 | 1980-05-09 | 옥심 유도체의 제조방법 |
Country Status (33)
Country | Link |
---|---|
US (1) | US4344789A (ko) |
KR (1) | KR840001968B1 (ko) |
AR (1) | AR230986A1 (ko) |
AT (1) | AT366883B (ko) |
AU (1) | AU526031B2 (ko) |
BG (1) | BG38333A3 (ko) |
BR (1) | BR8002850A (ko) |
CA (1) | CA1236851C (ko) |
CH (2) | CH652385A5 (ko) |
CS (1) | CS221909B2 (ko) |
DD (1) | DD151861A5 (ko) |
DE (2) | DE3017795A1 (ko) |
DK (1) | DK203980A (ko) |
EG (1) | EG14625A (ko) |
ES (1) | ES8104212A1 (ko) |
FI (1) | FI71731C (ko) |
FR (3) | FR2456087A1 (ko) |
GB (2) | GB2049695B (ko) |
GR (1) | GR67695B (ko) |
HU (1) | HU183134B (ko) |
IE (1) | IE49793B1 (ko) |
IL (1) | IL59958A (ko) |
IT (1) | IT1133087B (ko) |
LU (1) | LU82433A1 (ko) |
NL (1) | NL181430C (ko) |
NO (1) | NO149587C (ko) |
PH (1) | PH16450A (ko) |
PL (1) | PL134026B1 (ko) |
PT (1) | PT71222A (ko) |
RO (1) | RO79871A (ko) |
SE (1) | SE8003512L (ko) |
SU (1) | SU1005656A3 (ko) |
YU (1) | YU42506B (ko) |
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US4633000A (en) * | 1980-02-01 | 1986-12-30 | Rhone Poulenc Agrochimie | 2-nitro-5-(substituted-phenoxy) phenylalkanone oxime and imine derivatives as herbicides |
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DE3044810A1 (de) * | 1980-11-28 | 1982-07-01 | Bayer Ag, 5090 Leverkusen | Substituierte phenoxyzimtsaeurederivate, verfahren zu deren herstellung und deren verwendung als herbizide, sowie zwischenprodukte und deren herstellung |
US4509970A (en) * | 1981-12-17 | 1985-04-09 | Zoecon Corporation | Substituted phenylphosphinyloxy- and phosphinylthio-iminocarboxylates useful for the control of weeds |
DE3220526A1 (de) * | 1982-06-01 | 1983-12-01 | Bayer Ag, 5090 Leverkusen | Trifluormethylphenoxy-phenyl-derivate, verfahren zu ihrer herstellung und ihre verwendung als herbizide |
DK416583A (da) * | 1982-10-06 | 1984-04-07 | Hoffmann La Roche | Benzoesyrederivater med herbicid virkning |
US4504671A (en) * | 1982-10-15 | 1985-03-12 | Ppg Industries, Inc. | Method for preparing aldoxime or ketoxime-O-alkanoic acid |
US4900862A (en) * | 1983-03-28 | 1990-02-13 | American Cyanamid Company | Herbicidally active substituted diphenyl ether oxime derivatives |
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FR2549047B1 (fr) * | 1983-07-12 | 1986-03-21 | Rhone Poulenc Agrochimie | Nouveaux herbicides derives d'acides aryloxybenzenes carbonimides |
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JPH01233203A (ja) * | 1988-03-12 | 1989-09-19 | Mitsubishi Petrochem Co Ltd | 除草剤組成物 |
GB9013352D0 (en) * | 1990-06-14 | 1990-08-08 | Ici Plc | Herbicidal compounds |
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-
1980
- 1980-04-15 US US06/136,171 patent/US4344789A/en not_active Expired - Lifetime
- 1980-04-23 FI FI801303A patent/FI71731C/fi not_active IP Right Cessation
- 1980-04-30 IL IL59958A patent/IL59958A/xx unknown
- 1980-04-30 GR GR61817A patent/GR67695B/el unknown
- 1980-05-01 CA CA 351078 patent/CA1236851C/en not_active Expired
- 1980-05-07 YU YU1210/80A patent/YU42506B/xx unknown
- 1980-05-07 PL PL1980224072A patent/PL134026B1/pl unknown
- 1980-05-08 SU SU802924049A patent/SU1005656A3/ru active
- 1980-05-08 CS CS803251A patent/CS221909B2/cs unknown
- 1980-05-09 KR KR1019800001833A patent/KR840001968B1/ko active
- 1980-05-09 AT AT0248480A patent/AT366883B/de not_active IP Right Cessation
- 1980-05-09 IE IE961/80A patent/IE49793B1/en unknown
- 1980-05-09 ES ES491327A patent/ES8104212A1/es not_active Expired
- 1980-05-09 NO NO801373A patent/NO149587C/no unknown
- 1980-05-09 NL NLAANVRAGE8002681,A patent/NL181430C/xx not_active IP Right Cessation
- 1980-05-09 BG BG8047703A patent/BG38333A3/xx unknown
- 1980-05-09 CH CH2818/84A patent/CH652385A5/fr not_active IP Right Cessation
- 1980-05-09 DE DE19803017795 patent/DE3017795A1/de active Granted
- 1980-05-09 IT IT67734/80A patent/IT1133087B/it active
- 1980-05-09 AR AR280959A patent/AR230986A1/es active
- 1980-05-09 DE DE3051060A patent/DE3051060C2/de not_active Expired
- 1980-05-09 FR FR8010536A patent/FR2456087A1/fr active Granted
- 1980-05-09 HU HU801162A patent/HU183134B/hu not_active IP Right Cessation
- 1980-05-09 SE SE8003512A patent/SE8003512L/xx not_active Application Discontinuation
- 1980-05-09 AU AU58268/80A patent/AU526031B2/en not_active Ceased
- 1980-05-09 DK DK203980A patent/DK203980A/da not_active Application Discontinuation
- 1980-05-09 PT PT71222A patent/PT71222A/pt unknown
- 1980-05-09 BR BR8002850A patent/BR8002850A/pt unknown
- 1980-05-09 LU LU82433A patent/LU82433A1/fr unknown
- 1980-05-09 PH PH24000A patent/PH16450A/en unknown
- 1980-05-09 CH CH366780A patent/CH644588A5/fr not_active IP Right Cessation
- 1980-05-10 RO RO80101093A patent/RO79871A/ro unknown
- 1980-05-10 EG EG80290A patent/EG14625A/xx active
- 1980-05-12 GB GB8015658A patent/GB2049695B/en not_active Expired
- 1980-05-12 DD DD80221034A patent/DD151861A5/de not_active IP Right Cessation
- 1980-08-06 FR FR8017417A patent/FR2456085A1/fr not_active Withdrawn
- 1980-08-06 FR FR8017418A patent/FR2456088A1/fr active Granted
-
1983
- 1983-01-14 GB GB08300942A patent/GB2120233B/en not_active Expired
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
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KR20040012102A (ko) * | 2002-08-01 | 2004-02-11 | 이동수 | 부드럽고 가벼운 편사의 제조방법 |
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