KR840006228A - N-치환된 우레아의 제조방법 - Google Patents
N-치환된 우레아의 제조방법 Download PDFInfo
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- KR840006228A KR840006228A KR1019830004110A KR830004110A KR840006228A KR 840006228 A KR840006228 A KR 840006228A KR 1019830004110 A KR1019830004110 A KR 1019830004110A KR 830004110 A KR830004110 A KR 830004110A KR 840006228 A KR840006228 A KR 840006228A
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- Prior art keywords
- alkyl
- hydrogen
- formula
- alkoxy
- haloalkyl
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- 238000000034 method Methods 0.000 title claims 16
- -1 N-substituted urea Chemical class 0.000 title claims 9
- 125000000217 alkyl group Chemical group 0.000 claims 24
- 239000001257 hydrogen Substances 0.000 claims 17
- 229910052739 hydrogen Inorganic materials 0.000 claims 17
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 9
- 125000003545 alkoxy group Chemical group 0.000 claims 8
- 150000002431 hydrogen Chemical class 0.000 claims 8
- 125000003342 alkenyl group Chemical group 0.000 claims 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 6
- 125000004432 carbon atom Chemical group C* 0.000 claims 6
- 150000001875 compounds Chemical class 0.000 claims 6
- 229910052736 halogen Inorganic materials 0.000 claims 6
- 150000002367 halogens Chemical class 0.000 claims 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 6
- 229910052760 oxygen Inorganic materials 0.000 claims 6
- 239000001301 oxygen Substances 0.000 claims 6
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 4
- 229910052717 sulfur Chemical group 0.000 claims 4
- 239000011593 sulfur Chemical group 0.000 claims 4
- 125000006583 (C1-C3) haloalkyl group Chemical group 0.000 claims 3
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 3
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims 3
- 150000001412 amines Chemical class 0.000 claims 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 3
- 229910052794 bromium Inorganic materials 0.000 claims 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims 3
- 229910052731 fluorine Inorganic materials 0.000 claims 3
- 239000011737 fluorine Substances 0.000 claims 3
- 125000001424 substituent group Chemical group 0.000 claims 3
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 3
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims 2
- KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 claims 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims 2
- OBASDBHRXUCXKQ-UHFFFAOYSA-N [F].[Br] Chemical compound [F].[Br] OBASDBHRXUCXKQ-UHFFFAOYSA-N 0.000 claims 2
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 claims 2
- 229910052783 alkali metal Inorganic materials 0.000 claims 2
- 150000001340 alkali metals Chemical group 0.000 claims 2
- 125000003277 amino group Chemical group 0.000 claims 2
- 239000004202 carbamide Substances 0.000 claims 2
- 239000003054 catalyst Substances 0.000 claims 2
- 239000000460 chlorine Substances 0.000 claims 2
- 125000005843 halogen group Chemical group 0.000 claims 2
- 229910052763 palladium Inorganic materials 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims 2
- 125000005017 substituted alkenyl group Chemical group 0.000 claims 2
- 125000004317 1,3,5-triazin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=N1 0.000 claims 1
- DSJLHASGCALWKR-UHFFFAOYSA-N 1-(4,6-dimethoxy-1,3,5-triazin-2-yl)-3-[2-(3,3,3-trifluoroprop-1-enyl)phenyl]sulfonylurea Chemical compound COC1=NC(OC)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)C=CC(F)(F)F)=N1 DSJLHASGCALWKR-UHFFFAOYSA-N 0.000 claims 1
- HEGVBFAIMLQBHM-UHFFFAOYSA-N 1-(4-methoxy-6-methyl-1,3,5-triazin-2-yl)-3-[2-(3,3,3-trifluoroprop-1-enyl)phenyl]sulfonylurea Chemical compound COC1=NC(C)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)C=CC(F)(F)F)=N1 HEGVBFAIMLQBHM-UHFFFAOYSA-N 0.000 claims 1
- WFRWCLKPIVBOQX-UHFFFAOYSA-N 1-(benzenesulfonyl)-3-(triazin-4-yl)urea Chemical compound C=1C=CC=CC=1S(=O)(=O)NC(=O)NC1=CC=NN=N1 WFRWCLKPIVBOQX-UHFFFAOYSA-N 0.000 claims 1
- UJJQRJPAQKUPAQ-UHFFFAOYSA-N 1-(benzenesulfonyl)-3-pyrimidin-2-ylurea Chemical compound C=1C=CC=CC=1S(=O)(=O)NC(=O)NC1=NC=CC=N1 UJJQRJPAQKUPAQ-UHFFFAOYSA-N 0.000 claims 1
- CUQZZAFDEXJZEX-UHFFFAOYSA-N 2-(3,3,3-trifluoroprop-1-enyl)benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1C=CC(F)(F)F CUQZZAFDEXJZEX-UHFFFAOYSA-N 0.000 claims 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims 1
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- 150000005325 alkali earth metal hydroxides Chemical class 0.000 claims 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims 1
- 150000001336 alkenes Chemical group 0.000 claims 1
- 150000001408 amides Chemical class 0.000 claims 1
- 229910021529 ammonia Inorganic materials 0.000 claims 1
- 239000002585 base Substances 0.000 claims 1
- ALZKZGUTVJXYEF-UHFFFAOYSA-N benzenesulfonylcarbamic acid Chemical compound OC(=O)NS(=O)(=O)C1=CC=CC=C1 ALZKZGUTVJXYEF-UHFFFAOYSA-N 0.000 claims 1
- MZJUGRUTVANEDW-UHFFFAOYSA-N bromine fluoride Chemical group BrF MZJUGRUTVANEDW-UHFFFAOYSA-N 0.000 claims 1
- 125000001246 bromo group Chemical group Br* 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- ATDGTVJJHBUTRL-UHFFFAOYSA-N cyanogen bromide Chemical compound BrC#N ATDGTVJJHBUTRL-UHFFFAOYSA-N 0.000 claims 1
- 239000012954 diazonium Substances 0.000 claims 1
- 150000001989 diazonium salts Chemical class 0.000 claims 1
- 238000006193 diazotization reaction Methods 0.000 claims 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- 125000004438 haloalkoxy group Chemical group 0.000 claims 1
- 125000001188 haloalkyl group Chemical group 0.000 claims 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims 1
- 229910052740 iodine Inorganic materials 0.000 claims 1
- 239000011630 iodine Substances 0.000 claims 1
- 239000012948 isocyanate Substances 0.000 claims 1
- 150000002513 isocyanates Chemical class 0.000 claims 1
- 150000002540 isothiocyanates Chemical class 0.000 claims 1
- 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 claims 1
- 125000004674 methylcarbonyl group Chemical group CC(=O)* 0.000 claims 1
- UJYAZVSPFMJCLW-UHFFFAOYSA-N n-(oxomethylidene)benzenesulfonamide Chemical compound O=C=NS(=O)(=O)C1=CC=CC=C1 UJYAZVSPFMJCLW-UHFFFAOYSA-N 0.000 claims 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 1
- VSCGRMUDBNQJNB-UHFFFAOYSA-N pyrimidin-2-ylcarbamic acid Chemical compound OC(=O)NC1=NC=CC=N1 VSCGRMUDBNQJNB-UHFFFAOYSA-N 0.000 claims 1
- 125000001453 quaternary ammonium group Chemical group 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid Chemical compound NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 claims 1
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims 1
- XSYLPIPLYOCKKP-UHFFFAOYSA-N triazin-4-ylcarbamic acid Chemical compound OC(=O)NC1=CC=NN=N1 XSYLPIPLYOCKKP-UHFFFAOYSA-N 0.000 claims 1
- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C335/00—Thioureas, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C335/04—Derivatives of thiourea
- C07C335/16—Derivatives of thiourea having nitrogen atoms of thiourea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
-
- 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
- C07C311/65—N-sulfonylisocyanates
-
- 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
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides 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
- C07C311/15—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings
- C07C311/16—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the sulfonamide groups bound to hydrogen atoms or to an acyclic carbon atom
-
- 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
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/47—One nitrogen atom and one oxygen or sulfur atom, e.g. cytosine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D521/00—Heterocyclic compounds containing unspecified hetero rings
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- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Wood Science & Technology (AREA)
- Environmental Sciences (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Zoology (AREA)
- Pest Control & Pesticides (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Saccharide Compounds (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
- Lubricants (AREA)
Abstract
내용 없음
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (17)
- 하기식(Ⅱ)의 페닐설폰아미드와 하기 식(Ⅲ)의 N-피리미디닐카르바메이트 혼은 N-트리아지닐카르바메이트와 반응시키고, 하기식(Ⅵ)의 페닐설포닐이소시아내이트 혹은 페닐설포닐 이소티아시아 내이트와 하기식(Ⅴ)의 아민과 반응시키고, 하기식(Ⅱ)의 설포아미드와 하기식(Ⅵ)의 이소시아내이트 혹은 이소티오시아 내이트를 반응시키고, 하기식(Ⅶ)의 N-페닐설포닐-카르바메이트와 하기식(Ⅴ)의 아민을 반응시키고, 제조된 우레아를 아미드, 알카리 금속수산화물 혹은 알카리토금속 수산화기 혹은 사차암모늄 염기가 반응시켜서 염으로 전환시키는 단계로 구성되는 하기식(Ⅰ)의 N-페닐설포닐-N'-피리미디닐 우레아 혹은 N-페닐설포닐-N'-트리아지닐우레아의 제조법.상기 식에서, R1은 수소, 할로겐, 니트로, 아미노, C1-5알킬, C1-1할로알킬 또는 -Q-R7-COOR8또는 -(CO)n-NR9R10이고, R2는 수소, C1-4알킬, C1-4알콕시, C1-4알킬티오 C1-4할로알킬, C1-4할로알콕시, 할로겐 또는 알콕시알킬(4미만의 탄소 원자를 함유하는)이고 R3는 1개이상의 불소나 브롬원자로 치환되었거나 또는 1개이상의 히드록실, 시아노, 니트로, -(Y)mCO(Z)nR8, -SO2NR11R12, -S(O)p- C1-3할로알킬, -S(O)n-C-3-알킬기의 치환된 그리고 1개이상의 염소원자로부가 치환되기도 한 C2-10알케닐이고, R4는 C1-3알킬, C1-3할로알킬, C1-3알콕시 또는 C1-3할로알콕시이고, R5는 수소, 할로겐,- NR13R14, C1-5알킬, C1-3할로알킬, C1-3알콕시 또는 C1-2할로 알콕이고, R6는 수소, C1-3알킬 또는 C1-3알콕시이고, X는 산소나 황이고, E는 질소나 메틴기이고, R7는 할로겐이나 C1-3알콕시로 치환된 C1-4알킬, 또는 C3-5알케닐, R8은 C1-4알킬, C1-4할로알킬 또는 C1-4알콕시알킬이고, R9,R10,R11,R12,R13및 R14다른 각 독립기로서 수소나 C1-3알킬이고, Q는 산소, 황, 설피닐이나 설포닐기이고, Y는 산소, 황 또는 -NR16이고, R16은 수소나 C1-3알킬이고, Z는 산소, 황 또는 -NR17이고, R17은 수소나 C1-3알킬이고, m및 n은 각각 0이나 1이고, P는 0.1 또는 2임.
- 제1항에 있어서, X는 산소인 방법.
- 제1항에 있어서, R4와 R5는 함게 4탄소원자 이하인 방법.
- 제1항에 있어서, R6는 수소인 방법.
- 제1항에 있어서, R1과 R2는 수소인 방법.
- 제1항에 있어서, R3는 페닐핵에 올레핀기가 부가되는 치환된 알케닐기인 방법.
- 제1항에 있어서, R3는 설포닐기에 2위치에 있는 방법.
- 제6항에 있어서, 치환된 알케닐기가 2-4 탄소원자인 방법.
- 제6항에 있어서, 알케닐기의 치환체가 불소, 브롬, 니트로, 시아노, 메톡시, 에톡시카르보닐, 메틸카르보닐, 히드록실, 아세톡시, 메틸설포닐, 트리플루오로메틸설포닐, 트리플루오로메틸설설피닐 혹은 디메틸설파오일로 구성된 그룹에서 선택되는 방법.
- 제9항에 있어서, 알케닐기의 치환체가 불소 브롬, 히드록실, 시아노 혹은 아세톡시에서 선택되는 방법.
- 제1항에 있어서, X가 산소이고, R1,R2및 R6는 수소이고, R4와 R5는 함께 4 탄소원자이하이고, R3는 설포닐기의 2위치에 있으며 페닐핵에 올핀부가 되는 C2-4알케닐기이며, 불소 브롬, 니트로, 시아노메톡시, 아세톡시, 메톡시카르보닐, 에톡시카르보닐, 히드록시, 트리플루오로설포닐, 트리플루오로메틸설피닐, 메틸설포닐 혹은 디메틸설파오일로 치환되는 C2-4알케닐기인 방법.
- 제11항에 있어서, 알케닐기의 치환체가 불소, 시아노, 브롬, 히드록실 혹은 아세톡시에서 선택되는 방법.
- 제1항에 있어서, N-[2-(3,3,3-트리플루오로-1-프로펜-1-일)페닐설포닐]-N'-(4-메톡시-6-메틸-1,3,5-트리아진-2-일)우레아, N-[2-(3,3,3-트리플루오로-1-프로펜-1-일)페닐설포닐]-N'-(4,6-디메톡시-1,3,5-트리아진-2-일)우레아 및 N-[2-(2-브로모비닐)페닐설포닐]-N'-[4-메톡시-6-메틸-1,3,5-트리아진-2-일)우레아의 제조방법.
- 하기식(Ⅷ)의 아민을 디아조화하에 하기식(Ⅸ)의 디아조늄염을 제조하고, 하기식(ⅩI)는 화합물과 필라듐 촉매하에 반응시켯 하기식(ⅩI)의 화합물을 제조하고, 염화티오님 혹은 PCI5로 처리하여 염화하고, 이것을 암모니아로 처리하여 하기식(Ⅱa)를 제조하는 방법.상기식에서, T는 히드록실, OMCl,-NC, 또는 NHT4; M은 알칼리금속원자, M1은 알칼리금속원자; R1'는 수소, 할로겐, C1-5알킬, C1-4할로알킬, C1-4알콕시, 또는 -NO2; R2'는 수소, 할로겐, C1-4알킬, C1-4할로알킬, C1-4알콕기, C1-4할로알콕시 또는 탄소원자 4미만의 알콕시알킬; R3'는 -C(T1)=C(T2XT3)기;T1은 수소, C1-4알킬, 시아노 또는 COO-C1-4알킬;T2는 -COOR8-CONR9R10, -CH2COOR8, CH2C1-4-알콕시, CH(C1-4알킬) C1-4알콕시, -CH2CN, -CH2OCOCH3-CH(C1-4알킬)-OC-CH3, -S(O)qC1-3알킬, -S(O)qC1-3할로알킬; q는 0.1 또는 2, -CORf, -CH2CH(COOR8)2또는 1개이상의 불소나브롬원자로 치환된 C1-8알킬; T3는 수소, -COO-C1-4알킬 또는 할로겐원자로 치환되지 않은 C1-5알킬; T4는 수소, -CONH-C1-4알킬, -CONH-C1-4알킬 또는 -COO-페닐; 알킬기를 T1,T2및 T3는 8개미만의 탄소원자를 함유하며, R8, R9및 R10은 식(Ⅰ)과 같고, 조건부로 R1, R2,T1및 T3가 수소이고, 가 아미노기라면 T2는 -COO-C1-4알킬이 아니다. T'는 OH, OM 또는T"는 OM임.
- 제14항에 있어서, T1과 T2, 특히 T1은 수소이고 T는 아미노기인 방법.
- 제14항에 있어서, 2-(3,3,3-트리플루오로-1-프로펜-1-일)페닐설폰아미드 혹은 2-(2-브로비모닐)페닐설폰아미드인 방법.
- 제14항에 있어서, R1과 R2'가 브롬 혹은 요오드인 경우 하기식(ⅩⅡ)의 화합물과 식(Ⅹ)의 화합물을 팔라듐 촉매하에 반응시켜서 제조하는 방법.상기식에서, R1',R2' 및 T4는 식(Ⅱa)에 정의한 대로이고, D는 브롬 혹은 요오드임.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR1019900019331A KR920004189B1 (ko) | 1982-09-01 | 1990-11-28 | 신규의 페닐설폰류 화합물의 제조방법 |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH5201/82-0 | 1982-09-01 | ||
| CH520182 | 1982-09-01 | ||
| CH5201/82 | 1982-09-01 |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019900019331A Division KR920004189B1 (ko) | 1982-09-01 | 1990-11-28 | 신규의 페닐설폰류 화합물의 제조방법 |
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| Publication Number | Publication Date |
|---|---|
| KR840006228A true KR840006228A (ko) | 1984-11-22 |
| KR910005411B1 KR910005411B1 (ko) | 1991-07-29 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019830004110A KR910005411B1 (ko) | 1982-09-01 | 1983-09-01 | N-치환된 우레아의 제조방법 |
| KR1019900019331A KR920004189B1 (ko) | 1982-09-01 | 1990-11-28 | 신규의 페닐설폰류 화합물의 제조방법 |
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| Application Number | Title | Priority Date | Filing Date |
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| KR1019900019331A KR920004189B1 (ko) | 1982-09-01 | 1990-11-28 | 신규의 페닐설폰류 화합물의 제조방법 |
Country Status (18)
| Country | Link |
|---|---|
| US (3) | US4780125A (ko) |
| EP (2) | EP0102925B1 (ko) |
| JP (2) | JPH0613485B2 (ko) |
| KR (2) | KR910005411B1 (ko) |
| AT (2) | ATE65496T1 (ko) |
| AU (2) | AU567688B2 (ko) |
| BR (1) | BR8304727A (ko) |
| CA (1) | CA1223010A (ko) |
| CS (1) | CS257771B2 (ko) |
| CY (1) | CY1591A (ko) |
| DE (2) | DE3382358D1 (ko) |
| ES (1) | ES8505353A1 (ko) |
| HU (1) | HU192155B (ko) |
| IL (1) | IL69597A (ko) |
| PH (1) | PH21853A (ko) |
| RO (1) | RO87621A (ko) |
| SU (1) | SU1223827A3 (ko) |
| ZA (1) | ZA836449B (ko) |
Families Citing this family (30)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4780125A (en) * | 1982-09-01 | 1988-10-25 | Ciba-Geigy Corporation | N-phenylsulfonyl-N'-triazinylureas |
| BR8304878A (pt) * | 1982-09-10 | 1984-04-24 | Du Pont | Composto e processo para sua preparacao:composicao adequada e processo para controlar o crescimento de vegetacao indesejada |
| ATE62104T1 (de) * | 1984-04-11 | 1991-04-15 | Ciba Geigy Ag | Verfahren zur selektiven unkrautbekaempfung in nutzpflanzenkulturen. |
| US4981509A (en) * | 1984-05-24 | 1991-01-01 | E. I. Du Pont De Nemours And Company | Herbicidal sulfonamides |
| HU193933B (en) * | 1984-06-08 | 1987-12-28 | Nitrokemia Ipartelepek | Herbicide or plant growth stimulating agent comprising beta-cyclodextrin complex of benzolsulphonylurea derivative and process for preparing the active substances |
| EP0169815B1 (de) * | 1984-07-26 | 1988-11-02 | Ciba-Geigy Ag | N-Arylsulfonyl-N'-triazinyl- und -pyrimidinylharnstoffe |
| US4820337A (en) * | 1984-08-30 | 1989-04-11 | Bayer Aktiengesellschaft | 1-(2-oxyaminosulphonylphenylsulphonyl)-3-triazinyl-ureas |
| DE3518876A1 (de) * | 1984-08-30 | 1986-03-13 | Bayer Ag, 5090 Leverkusen | 1-(2-oxyaminosulfonylphenylsulfonyl)-3-heteroaryl-harnstoffe |
| DE3431932A1 (de) * | 1984-08-30 | 1986-03-06 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung von 1-(2-oxyaminosulfonylphenylsulfonyl)-3- heteroaryl-harnstoffen |
| US4566898A (en) * | 1984-09-07 | 1986-01-28 | E. I. Du Pont De Nemours And Company | Herbicidal sulfonamides |
| CA1232273A (en) * | 1984-12-11 | 1988-02-02 | James V. Hay | Herbicidal sulfonamides |
| CA1230120A (en) * | 1985-05-10 | 1987-12-08 | Gerald E. Lepone | Herbicidal o-carbomethoxysulfonylureas |
| US4685955A (en) * | 1985-06-03 | 1987-08-11 | E. I. Du Pont De Nemours And Company | Herbicidal sulfonamides |
| USH386H (en) | 1985-08-27 | 1987-12-01 | E. I. Du Pont De Nemours And Company | Herbicidal sulfonamides |
| US4764207A (en) * | 1986-03-27 | 1988-08-16 | E. I. Dupont De Nemours And Company | Herbicidal sulfonamides |
| US4759792A (en) * | 1986-06-05 | 1988-07-26 | Ciba-Geigy Corporation | Phenylsulfonylureas |
| US5215570A (en) * | 1988-10-20 | 1993-06-01 | Ciba-Geigy Corporation | Sulfamoylphenylureas |
| ES2069050T3 (es) * | 1989-01-11 | 1995-05-01 | Ciba Geigy Ag | Antidotos para mejorar la tolerancia de las plantas de cultivo frente a sustancias activas agroquimicas. |
| IE890149L (en) * | 1989-10-06 | 1990-07-19 | Du Pont | Sulfonylureas |
| MY136106A (en) * | 1990-09-06 | 2008-08-29 | Novartis Ag | Synergistic composition comprising a sulfonylurea anda thiadiazolo (3,4-a)pyridazine and method of selective weed control. |
| EP0512953B1 (de) * | 1991-05-06 | 1995-06-07 | Ciba-Geigy Ag | Verfahren zur Herstellung von Benzolsulfonamiden |
| AU3496493A (en) | 1992-02-21 | 1993-09-13 | Ciba-Geigy Ag | Sulfonylureas as herbicides |
| EP0558448A1 (de) * | 1992-02-26 | 1993-09-01 | Ciba-Geigy Ag | 1,5-Diphenylpyrazol-3-Carbonsäure-Derivate als Antidots für Sulfonylharnstoffherbizide |
| US5508402A (en) * | 1992-08-18 | 1996-04-16 | Ciba-Geigy Corporation | Process for the preparation of N,N'-substituted ureas |
| LT3943B (en) | 1993-12-23 | 1996-05-27 | Ciba Geigy Ag | Remedy for cultured plants protection, use of sulphamoyl-phenyl-carbamides for cultured plant protection, herbicidal preparation, process for preparing sulphamoyl-phenyl-carbamides |
| ATE242208T1 (de) * | 1997-01-29 | 2003-06-15 | Pfizer | Sulfonylharnstoff-derivate und ihre verwendung in der kontrolle der interleukin-1-aktivität |
| DE19748470A1 (de) * | 1997-11-03 | 1999-05-06 | Hoechst Schering Agrevo Gmbh | Carbamoylphenylsulfonylharnstoffe, Verfahren zu ihrer Herstellung und ihre Verwendung als Herbizide und Pflanzenwachstumsregulatoren |
| AU758538B2 (en) | 1998-12-07 | 2003-03-27 | University Of South Carolina Research Foundation | A colorant composition, a polymer nanocomposite comprising the colorant composition and articles produced therefrom |
| US20050281970A1 (en) * | 2004-06-16 | 2005-12-22 | Lamarca Louis J Ii | Lateral liner substrates |
| WO2014018021A1 (en) | 2012-07-24 | 2014-01-30 | Empire Technology Development Llc | Solution phase polydiacetylene synthesis by alkyne metathesis |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL121788C (ko) * | ||||
| DE2224831A1 (de) * | 1972-05-20 | 1973-11-29 | Bayer Ag | Sauer modifizierte terephthalsaeurepolyester |
| CA1082189A (en) * | 1976-04-07 | 1980-07-22 | George Levitt | Herbicidal sulfonamides |
| US4368069A (en) * | 1980-07-11 | 1983-01-11 | E. I. Du Pont De Nemours And Company | Herbicidal sulfonamides |
| CA1330438C (en) * | 1980-07-17 | 1994-06-28 | Willy Meyer | N-phenylsulfonyl-n'-pyrimidinyl-and-triazinylureas |
| DE3260229D1 (en) * | 1981-02-26 | 1984-07-19 | Ciba Geigy Ag | Amphoteric styrene derivatives |
| US4443245A (en) * | 1981-07-13 | 1984-04-17 | Ciba-Geigy Corporation | N-Phenylsulfonyl-N'-triazinylureas |
| US4443243A (en) * | 1981-07-16 | 1984-04-17 | Ciba-Geigy Corporation | N-Phenylsulfonyl-N-triazinylureas |
| US4545811A (en) * | 1981-08-06 | 1985-10-08 | Ciba-Geigy Corporation | N-Phenylsulfonyl-N'-triazinyl-ureas |
| US4780125A (en) * | 1982-09-01 | 1988-10-25 | Ciba-Geigy Corporation | N-phenylsulfonyl-N'-triazinylureas |
| BR8304878A (pt) * | 1982-09-10 | 1984-04-24 | Du Pont | Composto e processo para sua preparacao:composicao adequada e processo para controlar o crescimento de vegetacao indesejada |
| US4552960A (en) * | 1983-06-20 | 1985-11-12 | Eli Lilly And Company | Fungicidal amines |
| US4678502A (en) * | 1983-07-25 | 1987-07-07 | E. I. Du Pont De Nemours And Company | Herbicidal ortho-alkyl- and ortho-alkenyl-substituted benzenesulfonamides |
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1983
- 1983-08-22 US US06/525,366 patent/US4780125A/en not_active Expired - Lifetime
- 1983-08-26 DE DE8787107040T patent/DE3382358D1/de not_active Expired - Lifetime
- 1983-08-26 DE DE8383810386T patent/DE3378211D1/de not_active Expired
- 1983-08-26 EP EP83810386A patent/EP0102925B1/de not_active Expired
- 1983-08-26 AT AT87107040T patent/ATE65496T1/de active
- 1983-08-26 EP EP87107040A patent/EP0248245B1/de not_active Expired - Lifetime
- 1983-08-26 AT AT83810386T patent/ATE37874T1/de active
- 1983-08-29 RO RO83111958A patent/RO87621A/ro unknown
- 1983-08-30 CA CA000435654A patent/CA1223010A/en not_active Expired
- 1983-08-30 SU SU833643052A patent/SU1223827A3/ru active
- 1983-08-30 IL IL69597A patent/IL69597A/xx not_active IP Right Cessation
- 1983-08-30 HU HU833023A patent/HU192155B/hu not_active IP Right Cessation
- 1983-08-31 AU AU18580/83A patent/AU567688B2/en not_active Ceased
- 1983-08-31 BR BR8304727A patent/BR8304727A/pt not_active IP Right Cessation
- 1983-08-31 ZA ZA836449A patent/ZA836449B/xx unknown
- 1983-08-31 PH PH29474A patent/PH21853A/en unknown
- 1983-08-31 ES ES525248A patent/ES8505353A1/es not_active Expired
- 1983-08-31 CS CS836291A patent/CS257771B2/cs unknown
- 1983-09-01 JP JP58159112A patent/JPH0613485B2/ja not_active Expired - Lifetime
- 1983-09-01 KR KR1019830004110A patent/KR910005411B1/ko not_active IP Right Cessation
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1987
- 1987-11-26 AU AU81806/87A patent/AU591000B2/en not_active Ceased
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- 1990-01-12 US US07/464,578 patent/US5041603A/en not_active Expired - Fee Related
- 1990-08-31 JP JP2228521A patent/JPH03188058A/ja active Granted
- 1990-11-28 KR KR1019900019331A patent/KR920004189B1/ko not_active IP Right Cessation
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