EP0000936A1 - Indan-4-yl-N-alkyl-carbaminsäureester, Verfahren zu ihrer Herstellung sowie ihre Verwendung als Pflanzenschutzmittel - Google Patents
Indan-4-yl-N-alkyl-carbaminsäureester, Verfahren zu ihrer Herstellung sowie ihre Verwendung als Pflanzenschutzmittel Download PDFInfo
- Publication number
- EP0000936A1 EP0000936A1 EP78100706A EP78100706A EP0000936A1 EP 0000936 A1 EP0000936 A1 EP 0000936A1 EP 78100706 A EP78100706 A EP 78100706A EP 78100706 A EP78100706 A EP 78100706A EP 0000936 A1 EP0000936 A1 EP 0000936A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- alkyl
- spp
- carbamic acid
- indan
- hydroxy
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 1
- 241000255626 Tabanus <genus> Species 0.000 description 1
- 241000254109 Tenebrio molitor Species 0.000 description 1
- 241001454294 Tetranychus Species 0.000 description 1
- 241000511627 Tipula paludosa Species 0.000 description 1
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 1
- 241001238451 Tortrix viridana Species 0.000 description 1
- 241000255993 Trichoplusia ni Species 0.000 description 1
- 241000267823 Trogoderma Species 0.000 description 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical group ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
- 235000013447 Xanthosoma atrovirens Nutrition 0.000 description 1
- 240000001781 Xanthosoma sagittifolium Species 0.000 description 1
- 241000353223 Xenopsylla cheopis Species 0.000 description 1
- 241001466337 Yponomeuta Species 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- HFVAFDPGUJEFBQ-UHFFFAOYSA-M alizarin red S Chemical compound [Na+].O=C1C2=CC=CC=C2C(=O)C2=C1C=C(S([O-])(=O)=O)C(O)=C2O HFVAFDPGUJEFBQ-UHFFFAOYSA-M 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 150000008055 alkyl aryl sulfonates Chemical class 0.000 description 1
- 150000008051 alkyl sulfates Chemical class 0.000 description 1
- 229940045714 alkyl sulfonate alkylating agent Drugs 0.000 description 1
- 150000008052 alkyl sulfonates Chemical class 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 229960000892 attapulgite Drugs 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- 239000001273 butane Substances 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 150000008422 chlorobenzenes Chemical class 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 239000008199 coating composition Substances 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O GUJOJGAPFQRJSV-UHFFFAOYSA-N 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 239000010459 dolomite Substances 0.000 description 1
- 229910000514 dolomite Inorganic materials 0.000 description 1
- 238000010410 dusting Methods 0.000 description 1
- 238000005538 encapsulation Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000012173 estrus Effects 0.000 description 1
- WUDNUHPRLBTKOJ-UHFFFAOYSA-N ethyl isocyanate Chemical compound CCN=C=O WUDNUHPRLBTKOJ-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- 231100000162 fungitoxic Toxicity 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 239000001023 inorganic pigment Substances 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 238000006317 isomerization reaction Methods 0.000 description 1
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 229920000126 latex Polymers 0.000 description 1
- 229920005610 lignin Polymers 0.000 description 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical class [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
- 239000004579 marble Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- DTDRXKHXTWUPQY-UHFFFAOYSA-N methyl-(1,1,5,6-tetramethyl-2,3-dihydroinden-4-yl)carbamic acid Chemical compound CC1(CCC2=C(C(=C(C=C12)C)C)N(C(O)=O)C)C DTDRXKHXTWUPQY-UHFFFAOYSA-N 0.000 description 1
- LHXQFBLBIZSHLJ-UHFFFAOYSA-N methyl-(1,1,5-trimethyl-2,3-dihydroinden-4-yl)carbamic acid Chemical compound CC1(CCC2=C(C(=CC=C12)C)N(C(O)=O)C)C LHXQFBLBIZSHLJ-UHFFFAOYSA-N 0.000 description 1
- UFEJKYYYVXYMMS-UHFFFAOYSA-N methylcarbamic acid Chemical class CNC(O)=O UFEJKYYYVXYMMS-UHFFFAOYSA-N 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 239000011733 molybdenum Substances 0.000 description 1
- 229910052901 montmorillonite Inorganic materials 0.000 description 1
- 230000000877 morphologic effect Effects 0.000 description 1
- 230000004660 morphological change Effects 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- HNHVTXYLRVGMHD-UHFFFAOYSA-N n-butyl isocyanate Chemical compound CCCCN=C=O HNHVTXYLRVGMHD-UHFFFAOYSA-N 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- 229920005615 natural polymer Polymers 0.000 description 1
- JCXJVPUVTGWSNB-UHFFFAOYSA-N nitrogen dioxide Inorganic materials O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 229910052625 palygorskite Inorganic materials 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 239000003531 protein hydrolysate Substances 0.000 description 1
- 239000008262 pumice Substances 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229910052624 sepiolite Inorganic materials 0.000 description 1
- 235000019355 sepiolite Nutrition 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 230000000391 smoking effect Effects 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 229920001059 synthetic polymer Polymers 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 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
- 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
- A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
- A01N47/22—O-Aryl or S-Aryl esters thereof
Definitions
- N-methyl-carbamic acid esters of 4-hydroxy-indanes are insecticidal (compare DT-AS 1 249 261 (Le A 10 048) or US Pat. No. 3,597,472 and DT-OS 1 768 555 (Le A 11 471) or US Pat. No. 3,712,915).
- N-trichloromethylthio-tetrahydrophthalimide has strong fungicidal properties (see Science, 115, 84 (1952)).
- this active ingredient which is important in practice and is known worldwide, has only a protective activity.
- the plants are sprayed with the spray liquid which has been prepared in the above-mentioned manner until it drips. Then the plants come back into the greenhouse.
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2739192 | 1977-08-31 | ||
| DE19772739192 DE2739192A1 (de) | 1977-08-31 | 1977-08-31 | Indan-4-yl-n-alkyl-carbaminsaeureester, verfahren zu ihrer herstellung sowie ihre verwendung als pflanzenschutzmittel |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| EP0000936A1 true EP0000936A1 (de) | 1979-03-07 |
Family
ID=6017748
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP78100706A Withdrawn EP0000936A1 (de) | 1977-08-31 | 1978-08-21 | Indan-4-yl-N-alkyl-carbaminsäureester, Verfahren zu ihrer Herstellung sowie ihre Verwendung als Pflanzenschutzmittel |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US4316912A (cs) |
| EP (1) | EP0000936A1 (cs) |
| JP (1) | JPS5446756A (cs) |
| AT (1) | ATA631878A (cs) |
| AU (1) | AU3943378A (cs) |
| BR (1) | BR7805616A (cs) |
| CS (1) | CS199219B2 (cs) |
| DD (1) | DD138143A5 (cs) |
| DE (1) | DE2739192A1 (cs) |
| DK (1) | DK384378A (cs) |
| IL (1) | IL55443A0 (cs) |
| IT (1) | IT7827110A0 (cs) |
| PL (1) | PL110898B1 (cs) |
| ZA (1) | ZA784947B (cs) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5666075A (en) * | 1995-04-13 | 1997-09-09 | Hewlett-Packard Company | Electronic circuit comprising a comparator |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3002202A1 (de) * | 1980-01-22 | 1981-08-06 | Bayer Ag, 5090 Leverkusen | Indan-4-yl-n-alkyl-carbaminsaeureester, verfahren zu ihrer herstellung sowie ihre verwendung als fungizide |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1249261B (de) * | 1966-06-18 | 1967-09-07 | Farbenfabriken Bayer Aktiengesellschaft, Leverkusen | Verfahren zur Herstellung von Indanyl-N-methylcarbaminsäureestern |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3084096A (en) * | 1955-08-29 | 1963-04-02 | Union Carbide Corp | Indanyl n-methyl carbamate |
| US2870057A (en) * | 1957-11-26 | 1959-01-20 | Gulf Research Development Co | 4- or 5-indanyl n-methyl carbamate |
| IL32061A (en) * | 1968-05-25 | 1972-08-30 | Bayer Ag | Indanyl-n-methylcarbamic acid esters,their preparation and use for pest control |
-
1977
- 1977-08-31 DE DE19772739192 patent/DE2739192A1/de active Pending
-
1978
- 1978-08-21 EP EP78100706A patent/EP0000936A1/de not_active Withdrawn
- 1978-08-25 DD DD78207489A patent/DD138143A5/xx unknown
- 1978-08-29 IT IT7827110A patent/IT7827110A0/it unknown
- 1978-08-29 IL IL7855443A patent/IL55443A0/xx unknown
- 1978-08-29 JP JP10450078A patent/JPS5446756A/ja active Pending
- 1978-08-30 BR BR7805616A patent/BR7805616A/pt unknown
- 1978-08-30 ZA ZA00784947A patent/ZA784947B/xx unknown
- 1978-08-30 CS CS785627A patent/CS199219B2/cs unknown
- 1978-08-30 DK DK384378A patent/DK384378A/da unknown
- 1978-08-30 PL PL1978209289A patent/PL110898B1/pl unknown
- 1978-08-31 AT AT631878A patent/ATA631878A/de not_active Application Discontinuation
- 1978-08-31 AU AU39433/78A patent/AU3943378A/en active Pending
-
1980
- 1980-02-19 US US06/122,159 patent/US4316912A/en not_active Expired - Lifetime
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1249261B (de) * | 1966-06-18 | 1967-09-07 | Farbenfabriken Bayer Aktiengesellschaft, Leverkusen | Verfahren zur Herstellung von Indanyl-N-methylcarbaminsäureestern |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5666075A (en) * | 1995-04-13 | 1997-09-09 | Hewlett-Packard Company | Electronic circuit comprising a comparator |
Also Published As
| Publication number | Publication date |
|---|---|
| CS199219B2 (en) | 1980-07-31 |
| JPS5446756A (en) | 1979-04-12 |
| US4316912A (en) | 1982-02-23 |
| BR7805616A (pt) | 1979-04-10 |
| IL55443A0 (en) | 1978-10-31 |
| DE2739192A1 (de) | 1979-03-08 |
| DK384378A (da) | 1979-03-01 |
| IT7827110A0 (it) | 1978-08-29 |
| PL209289A1 (pl) | 1979-06-04 |
| AU3943378A (en) | 1980-03-06 |
| ATA631878A (de) | 1980-03-15 |
| ZA784947B (en) | 1979-08-29 |
| PL110898B1 (en) | 1980-08-30 |
| DD138143A5 (de) | 1979-10-17 |
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Inventor name: BRANDES, WILHELM, DR. Inventor name: GROTKOPP, DETLEF, DR. Inventor name: SCHEINPFLUG, HANS, DR. Inventor name: ROESSLER, PETER, DR. Inventor name: WEDEMEYER, DR. |