CH644356A5 - 4-phenylthioalkansulfonanilide sowie diese verbindungen enthaltende mittel zur regulierung des pflanzenwachstums. - Google Patents
4-phenylthioalkansulfonanilide sowie diese verbindungen enthaltende mittel zur regulierung des pflanzenwachstums. Download PDFInfo
- Publication number
- CH644356A5 CH644356A5 CH67980A CH67980A CH644356A5 CH 644356 A5 CH644356 A5 CH 644356A5 CH 67980 A CH67980 A CH 67980A CH 67980 A CH67980 A CH 67980A CH 644356 A5 CH644356 A5 CH 644356A5
- Authority
- CH
- Switzerland
- Prior art keywords
- halogen atom
- formula
- compounds
- salts
- hydrogen
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims description 47
- 230000008635 plant growth Effects 0.000 title claims description 9
- 230000001105 regulatory effect Effects 0.000 title claims description 5
- 150000003839 salts Chemical class 0.000 claims description 26
- 238000000034 method Methods 0.000 claims description 24
- 241000196324 Embryophyta Species 0.000 claims description 21
- 125000005843 halogen group Chemical group 0.000 claims description 12
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 claims description 12
- 230000008569 process Effects 0.000 claims description 10
- 239000002904 solvent Substances 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 claims description 7
- 125000006372 monohalo methyl group Chemical group 0.000 claims description 6
- 239000003795 chemical substances by application Substances 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- TZQVSGOOKNNDFU-UHFFFAOYSA-N 4-phenylsulfanylaniline Chemical class C1=CC(N)=CC=C1SC1=CC=CC=C1 TZQVSGOOKNNDFU-UHFFFAOYSA-N 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 239000004480 active ingredient Substances 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 36
- 239000000243 solution Substances 0.000 description 25
- 239000007787 solid Substances 0.000 description 20
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- 238000006243 chemical reaction Methods 0.000 description 11
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- 239000000047 product Substances 0.000 description 11
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- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
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- 239000012359 Methanesulfonyl chloride Substances 0.000 description 2
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- 239000007868 Raney catalyst Substances 0.000 description 2
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 2
- 229910000564 Raney nickel Inorganic materials 0.000 description 2
- 235000017016 Setaria faberi Nutrition 0.000 description 2
- 241001355178 Setaria faberi Species 0.000 description 2
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- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 125000001931 aliphatic group Chemical class 0.000 description 2
- YCOXTKKNXUZSKD-UHFFFAOYSA-N as-o-xylenol Natural products CC1=CC=C(O)C=C1C YCOXTKKNXUZSKD-UHFFFAOYSA-N 0.000 description 2
- FFBHFFJDDLITSX-UHFFFAOYSA-N benzyl N-[2-hydroxy-4-(3-oxomorpholin-4-yl)phenyl]carbamate Chemical compound OC1=C(NC(=O)OCC2=CC=CC=C2)C=CC(=C1)N1CCOCC1=O FFBHFFJDDLITSX-UHFFFAOYSA-N 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- KQDDQXNVESLJNO-UHFFFAOYSA-N chloromethanesulfonyl chloride Chemical compound ClCS(Cl)(=O)=O KQDDQXNVESLJNO-UHFFFAOYSA-N 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
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- REBXONLCWPJVRV-UHFFFAOYSA-N oxido-(4-phenylphenyl)-sulfanylideneazanium Chemical compound C1=CC([N+](=S)[O-])=CC=C1C1=CC=CC=C1 REBXONLCWPJVRV-UHFFFAOYSA-N 0.000 description 2
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- 239000003337 fertilizer Substances 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 229960002442 glucosamine Drugs 0.000 description 1
- 230000012010 growth Effects 0.000 description 1
- 229910001385 heavy metal Inorganic materials 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 229910017053 inorganic salt Inorganic materials 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 159000000014 iron salts Chemical class 0.000 description 1
- 238000003973 irrigation Methods 0.000 description 1
- 230000002262 irrigation Effects 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 159000000003 magnesium salts Chemical class 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- ZGEGCLOFRBLKSE-UHFFFAOYSA-N methylene hexane Natural products CCCCCC=C ZGEGCLOFRBLKSE-UHFFFAOYSA-N 0.000 description 1
- 235000019713 millet Nutrition 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- BMLIZLVNXIYGCK-UHFFFAOYSA-N monuron Chemical compound CN(C)C(=O)NC1=CC=C(Cl)C=C1 BMLIZLVNXIYGCK-UHFFFAOYSA-N 0.000 description 1
- 239000005645 nematicide Substances 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- FIKAKWIAUPDISJ-UHFFFAOYSA-L paraquat dichloride Chemical compound [Cl-].[Cl-].C1=C[N+](C)=CC=C1C1=CC=[N+](C)C=C1 FIKAKWIAUPDISJ-UHFFFAOYSA-L 0.000 description 1
- 239000013459 phenoxy herbicide Substances 0.000 description 1
- 239000005648 plant growth regulator Substances 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- ODCWYMIRDDJXKW-UHFFFAOYSA-N simazine Chemical compound CCNC1=NC(Cl)=NC(NCC)=N1 ODCWYMIRDDJXKW-UHFFFAOYSA-N 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- HYHCSLBZRBJJCH-UHFFFAOYSA-M sodium hydrosulfide Chemical compound [Na+].[SH-] HYHCSLBZRBJJCH-UHFFFAOYSA-M 0.000 description 1
- VGTPCRGMBIAPIM-UHFFFAOYSA-M sodium thiocyanate Chemical compound [Na+].[S-]C#N VGTPCRGMBIAPIM-UHFFFAOYSA-M 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 230000007480 spreading Effects 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 125000005031 thiocyano group Chemical group S(C#N)* 0.000 description 1
- 239000011573 trace mineral Substances 0.000 description 1
- 235000013619 trace mineral Nutrition 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Classifications
-
- 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
- A01N41/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom
- A01N41/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom containing a sulfur-to-oxygen double bond
- A01N41/10—Sulfones; Sulfoxides
-
- 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
- A01N41/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom
- A01N41/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom containing a sulfur-to-oxygen double bond
- A01N41/04—Sulfonic acids; Derivatives thereof
- A01N41/06—Sulfonic acid amides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Dentistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Plant Pathology (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US702679A | 1979-01-29 | 1979-01-29 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH644356A5 true CH644356A5 (de) | 1984-07-31 |
Family
ID=21723794
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH67980A CH644356A5 (de) | 1979-01-29 | 1980-01-28 | 4-phenylthioalkansulfonanilide sowie diese verbindungen enthaltende mittel zur regulierung des pflanzenwachstums. |
Country Status (14)
| Country | Link |
|---|---|
| JP (1) | JPS55129264A (enExample) |
| AR (2) | AR222206A1 (enExample) |
| AU (1) | AU533016B2 (enExample) |
| BE (1) | BE881404A (enExample) |
| BR (1) | BR8000534A (enExample) |
| CA (1) | CA1134385A (enExample) |
| CH (1) | CH644356A5 (enExample) |
| DE (1) | DE3002905A1 (enExample) |
| FR (1) | FR2447369B1 (enExample) |
| GB (1) | GB2041369B (enExample) |
| IN (1) | IN151746B (enExample) |
| IT (1) | IT1188897B (enExample) |
| NL (1) | NL8000488A (enExample) |
| ZA (1) | ZA80273B (enExample) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4331817A (en) * | 1981-01-16 | 1982-05-25 | Minnesota Mining And Manufacturing Co. | Process for the preparation of 4-arylthioanilines |
| CN103242238B (zh) * | 2013-05-10 | 2016-04-20 | 常州齐晖药业有限公司 | 一种芬苯达唑的制备方法 |
| CN105152994A (zh) * | 2015-09-28 | 2015-12-16 | 浙江汇能动物药品有限公司 | 一种芬苯达唑中间体2-氯-4-苯硫基硝基苯的制备方法 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1188591A (fr) * | 1956-12-08 | 1959-09-23 | Bayer Ag | Agents de protection contre les parasites des matières textiles et contre l'attaque des bactéries et des moisissures |
| US4005141A (en) * | 1972-07-03 | 1977-01-25 | Minnesota Mining And Manufacturing Company | Perfluoroalkylsulfonamidoaryl compounds |
| US3948987A (en) * | 1974-04-19 | 1976-04-06 | Minnesota Mining And Manufacturing Company | Substituted methanesulfonanilides |
| US3996277A (en) * | 1974-11-14 | 1976-12-07 | Minnesota Mining And Manufacturing Company | 4-Methylthio-2-trifluoromethylmethanesulfonanilide and derivatives thereof |
| JPS5934180B2 (ja) * | 1976-01-22 | 1984-08-21 | ミネソタ・マイニング・アンド・アニフアクチユアリング・カンパニ− | 新規４−メチル／２−トリフルオルメチルメタンスルホンアニリド |
| DE2703477A1 (de) * | 1977-01-28 | 1978-08-03 | Bayer Ag | Chlormethansulfonsaeureanilide, verfahren zu ihrer herstellung sowie ihre verwendung als herbizide |
| CA1091695A (en) * | 1977-04-11 | 1980-12-16 | Sharon L. Ruffing | 4-alkylthio-2-trifluoromethylalkane-sulfonanilides and derivatives thereof |
| DE2845997A1 (de) * | 1978-10-23 | 1980-04-30 | Bayer Ag | Pflanzenwachstumsregulierende mittel, verfahren zu ihrer herstellung und ihre verwendung zur regulierung des pflanzenwachstums |
| DE2845996A1 (de) * | 1978-10-23 | 1980-04-30 | Bayer Ag | Herbizide mittel, verfahren zu ihrer herstellung und ihre verwendung zur bekaempfung von unkraeutern |
-
1980
- 1980-01-16 ZA ZA00800273A patent/ZA80273B/xx unknown
- 1980-01-17 CA CA000343895A patent/CA1134385A/en not_active Expired
- 1980-01-22 AR AR279710A patent/AR222206A1/es active
- 1980-01-25 NL NL8000488A patent/NL8000488A/nl not_active Application Discontinuation
- 1980-01-25 AU AU54980/80A patent/AU533016B2/en not_active Ceased
- 1980-01-28 DE DE19803002905 patent/DE3002905A1/de not_active Withdrawn
- 1980-01-28 IN IN99/CAL/80A patent/IN151746B/en unknown
- 1980-01-28 CH CH67980A patent/CH644356A5/de not_active IP Right Cessation
- 1980-01-28 FR FR8001765A patent/FR2447369B1/fr not_active Expired
- 1980-01-28 JP JP868580A patent/JPS55129264A/ja active Pending
- 1980-01-28 IT IT47727/80A patent/IT1188897B/it active
- 1980-01-28 BR BR8000534A patent/BR8000534A/pt not_active IP Right Cessation
- 1980-01-28 AR AR279769A patent/AR223203A1/es active
- 1980-01-28 GB GB8002852A patent/GB2041369B/en not_active Expired
- 1980-01-29 BE BE0/199153A patent/BE881404A/fr not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| FR2447369A1 (fr) | 1980-08-22 |
| AR222206A1 (es) | 1981-04-30 |
| AR223203A1 (es) | 1981-07-31 |
| AU533016B2 (en) | 1983-10-27 |
| BR8000534A (pt) | 1980-10-21 |
| IN151746B (enExample) | 1983-07-23 |
| AU5498080A (en) | 1980-08-07 |
| IT8047727A0 (it) | 1980-01-28 |
| ZA80273B (en) | 1981-03-25 |
| JPS55129264A (en) | 1980-10-06 |
| DE3002905A1 (de) | 1980-07-31 |
| BE881404A (fr) | 1980-07-29 |
| NL8000488A (nl) | 1980-07-31 |
| GB2041369A (en) | 1980-09-10 |
| IT1188897B (it) | 1988-01-28 |
| CA1134385A (en) | 1982-10-26 |
| IT8047727A1 (it) | 1981-07-28 |
| FR2447369B1 (fr) | 1985-08-09 |
| GB2041369B (en) | 1983-05-05 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased | ||
| PL | Patent ceased |