NO116567B - - Google Patents
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- Publication number
- NO116567B NO116567B NO66164608A NO16460866A NO116567B NO 116567 B NO116567 B NO 116567B NO 66164608 A NO66164608 A NO 66164608A NO 16460866 A NO16460866 A NO 16460866A NO 116567 B NO116567 B NO 116567B
- Authority
- NO
- Norway
- Prior art keywords
- propyne
- carbamate
- iodo
- methyl
- hydrogen
- Prior art date
Links
- -1 5-pyrazolyl residue Chemical group 0.000 claims description 25
- 239000002917 insecticide Substances 0.000 claims description 17
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims description 11
- 150000001875 compounds Chemical class 0.000 claims description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims description 11
- 239000001257 hydrogen Substances 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 150000002431 hydrogen Chemical class 0.000 claims description 7
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- CVXBEEMKQHEXEN-UHFFFAOYSA-N carbaryl Chemical compound C1=CC=C2C(OC(=O)NC)=CC=CC2=C1 CVXBEEMKQHEXEN-UHFFFAOYSA-N 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 125000001624 naphthyl group Chemical group 0.000 claims description 4
- 125000003282 alkyl amino group Chemical group 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical group C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 2
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 2
- YNEVBPNZHBAYOA-UHFFFAOYSA-N Mexacarbate Chemical compound CNC(=O)OC1=CC(C)=C(N(C)C)C(C)=C1 YNEVBPNZHBAYOA-UHFFFAOYSA-N 0.000 claims description 2
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical class [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 2
- 239000004480 active ingredient Substances 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 125000004434 sulfur atom Chemical group 0.000 claims description 2
- 125000005277 alkyl imino group Chemical group 0.000 claims 1
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 14
- 241000255925 Diptera Species 0.000 description 13
- 230000000749 insecticidal effect Effects 0.000 description 10
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 241000238631 Hexapoda Species 0.000 description 5
- 239000013543 active substance Substances 0.000 description 4
- 239000012141 concentrate Substances 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 230000002195 synergetic effect Effects 0.000 description 4
- OTYZDIRNFDVXFG-UHFFFAOYSA-N (2-butylphenyl) n-methylcarbamate Chemical compound CCCCC1=CC=CC=C1OC(=O)NC OTYZDIRNFDVXFG-UHFFFAOYSA-N 0.000 description 3
- 241000254173 Coleoptera Species 0.000 description 3
- 241000255777 Lepidoptera Species 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
- 241000257226 Muscidae Species 0.000 description 3
- 241000255588 Tephritidae Species 0.000 description 3
- 150000002170 ethers Chemical class 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 241000255601 Drosophila melanogaster Species 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- ISFRDFNARBTUQD-UHFFFAOYSA-N [1-nitro-1-(1-nitro-1-phenylprop-2-ynoxy)prop-2-ynyl]benzene Chemical compound [N+](=O)([O-])C(C#C)(C1=CC=CC=C1)OC(C#C)([N+](=O)[O-])C1=CC=CC=C1 ISFRDFNARBTUQD-UHFFFAOYSA-N 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 235000021186 dishes Nutrition 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000003995 emulsifying agent Substances 0.000 description 2
- 235000013312 flour Nutrition 0.000 description 2
- 235000013305 food Nutrition 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 238000011200 topical administration Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- NNJPGOLRFBJNIW-HNNXBMFYSA-N (-)-demecolcine Chemical compound C1=C(OC)C(=O)C=C2[C@@H](NC)CCC3=CC(OC)=C(OC)C(OC)=C3C2=C1 NNJPGOLRFBJNIW-HNNXBMFYSA-N 0.000 description 1
- YRIHKKNMJAKBPN-UHFFFAOYSA-N (2-aminophenyl)-methylcarbamic acid Chemical compound OC(=O)N(C)C1=CC=CC=C1N YRIHKKNMJAKBPN-UHFFFAOYSA-N 0.000 description 1
- OZKIGSRXFXRIRK-UHFFFAOYSA-N (4-ethylphenyl)-methylcarbamic acid Chemical compound C(C)C1=CC=C(N(C(O)=O)C)C=C1 OZKIGSRXFXRIRK-UHFFFAOYSA-N 0.000 description 1
- LSHNYKWWYJXHSU-UHFFFAOYSA-N 1h-pyrazol-5-yl carbamate Chemical class NC(=O)OC=1C=CNN=1 LSHNYKWWYJXHSU-UHFFFAOYSA-N 0.000 description 1
- HSQFVBWFPBKHEB-UHFFFAOYSA-N 2,3,4-trichlorophenol Chemical compound OC1=CC=C(Cl)C(Cl)=C1Cl HSQFVBWFPBKHEB-UHFFFAOYSA-N 0.000 description 1
- XGCHAIDDPMFRLJ-UHFFFAOYSA-N 2,3,6-trichlorophenol Chemical compound OC1=C(Cl)C=CC(Cl)=C1Cl XGCHAIDDPMFRLJ-UHFFFAOYSA-N 0.000 description 1
- QGRKONUHHGBHRB-UHFFFAOYSA-N 2,3-dichlorobenzenethiol Chemical compound SC1=CC=CC(Cl)=C1Cl QGRKONUHHGBHRB-UHFFFAOYSA-N 0.000 description 1
- OKZBZIALAKCGTJ-UHFFFAOYSA-N 2,4-dichloro-1-prop-2-ynoxynaphthalene Chemical compound C1=CC=CC2=C(OCC#C)C(Cl)=CC(Cl)=C21 OKZBZIALAKCGTJ-UHFFFAOYSA-N 0.000 description 1
- YAESYRWEEVNLOA-UHFFFAOYSA-N 4-chloro-2-nitrobenzenethiol Chemical compound [O-][N+](=O)C1=CC(Cl)=CC=C1S YAESYRWEEVNLOA-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- 206010002091 Anaesthesia Diseases 0.000 description 1
- NWLZUNOZAOJBJN-UHFFFAOYSA-N CN(C)C1=CC=C(N(C)C(O)=O)C=C1C Chemical compound CN(C)C1=CC=C(N(C)C(O)=O)C=C1C NWLZUNOZAOJBJN-UHFFFAOYSA-N 0.000 description 1
- 235000008733 Citrus aurantifolia Nutrition 0.000 description 1
- VDYNBBYNSBUSRY-UHFFFAOYSA-N ClC1=C(C=CC(=C1)Cl)C(C#C)OC(C#C)C1=C(C=C(C=C1)Cl)Cl Chemical class ClC1=C(C=CC(=C1)Cl)C(C#C)OC(C#C)C1=C(C=C(C=C1)Cl)Cl VDYNBBYNSBUSRY-UHFFFAOYSA-N 0.000 description 1
- 241000894428 Gonioctena fornicata Species 0.000 description 1
- 241000506680 Haemulon melanurum Species 0.000 description 1
- 241001508566 Hypera postica Species 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- 240000007594 Oryza sativa Species 0.000 description 1
- 235000007164 Oryza sativa Nutrition 0.000 description 1
- 206010033799 Paralysis Diseases 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- DTAPQAJKAFRNJB-UHFFFAOYSA-N Promecarb Chemical compound CNC(=O)OC1=CC(C)=CC(C(C)C)=C1 DTAPQAJKAFRNJB-UHFFFAOYSA-N 0.000 description 1
- 235000011941 Tilia x europaea Nutrition 0.000 description 1
- 241000254112 Tribolium confusum Species 0.000 description 1
- 241000255993 Trichoplusia ni Species 0.000 description 1
- VXSIXFKKSNGRRO-MXOVTSAMSA-N [(1s)-2-methyl-4-oxo-3-[(2z)-penta-2,4-dienyl]cyclopent-2-en-1-yl] (1r,3r)-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropane-1-carboxylate;[(1s)-2-methyl-4-oxo-3-[(2z)-penta-2,4-dienyl]cyclopent-2-en-1-yl] (1r,3r)-3-[(e)-3-methoxy-2-methyl-3-oxoprop-1-enyl Chemical class CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)O[C@@H]1C(C)=C(C\C=C/C=C)C(=O)C1.CC1(C)[C@H](/C=C(\C)C(=O)OC)[C@H]1C(=O)O[C@@H]1C(C)=C(C\C=C/C=C)C(=O)C1 VXSIXFKKSNGRRO-MXOVTSAMSA-N 0.000 description 1
- VNWUXBYEGRWYIZ-UHFFFAOYSA-N [4-(dimethylamino)-3,5-dimethylphenyl]-methylcarbamic acid Chemical compound CN(C)C1=C(C)C=C(N(C)C(O)=O)C=C1C VNWUXBYEGRWYIZ-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 230000037005 anaesthesia Effects 0.000 description 1
- 239000000440 bentonite Substances 0.000 description 1
- 229910000278 bentonite Inorganic materials 0.000 description 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000012876 carrier material Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 230000037406 food intake Effects 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 239000010440 gypsum Substances 0.000 description 1
- 229910052602 gypsum Inorganic materials 0.000 description 1
- 230000002140 halogenating effect Effects 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 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
- 231100000225 lethality Toxicity 0.000 description 1
- 239000004571 lime Substances 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- GYKXQTKSWLAUIT-UHFFFAOYSA-N m-cumenyl methylcarbamate Chemical compound CNC(=O)OC1=CC=CC(C(C)C)=C1 GYKXQTKSWLAUIT-UHFFFAOYSA-N 0.000 description 1
- 230000000873 masking effect Effects 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- DZFMIQZOBRPZNJ-UHFFFAOYSA-N methyl-(3-methylphenyl)carbamic acid Chemical compound OC(=O)N(C)C1=CC=CC(C)=C1 DZFMIQZOBRPZNJ-UHFFFAOYSA-N 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 239000010815 organic waste Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- AIQRJSXKXVZCJO-UHFFFAOYSA-N prop-2-ynoxybenzene Chemical class C#CCOC1=CC=CC=C1 AIQRJSXKXVZCJO-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- HYJYGLGUBUDSLJ-UHFFFAOYSA-N pyrethrin Natural products CCC(=O)OC1CC(=C)C2CC3OC3(C)C2C2OC(=O)C(=C)C12 HYJYGLGUBUDSLJ-UHFFFAOYSA-N 0.000 description 1
- 229940070846 pyrethrins Drugs 0.000 description 1
- 239000002728 pyrethroid Substances 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 239000012488 sample solution Substances 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 235000020183 skimmed milk Nutrition 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000011885 synergistic combination Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 210000000115 thoracic cavity Anatomy 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
- C07D317/62—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to atoms of the carbocyclic ring
- C07D317/64—Oxygen atoms
-
- 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
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (11)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US43320965A | 1965-02-16 | 1965-02-16 | |
| US48594765A | 1965-09-08 | 1965-09-08 | |
| US48590465A | 1965-09-08 | 1965-09-08 | |
| US48591165A | 1965-09-08 | 1965-09-08 | |
| US48593465A | 1965-09-08 | 1965-09-08 | |
| US48590865A | 1965-09-08 | 1965-09-08 | |
| US48595165A | 1965-09-08 | 1965-09-08 | |
| US48592265A | 1965-09-08 | 1965-09-08 | |
| US486545A US3362871A (en) | 1965-02-16 | 1965-09-10 | Novel insecticidal carbamate-propar-gylaryl ether compositions |
| US53137166A | 1966-03-03 | 1966-03-03 | |
| DEH0060346 | 1966-08-26 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO116567B true NO116567B (de) | 1969-04-14 |
Family
ID=27581505
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO161707A NO118909B (de) | 1965-02-16 | 1966-02-15 | |
| NO66164608A NO116567B (de) | 1965-02-16 | 1966-09-07 |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO161707A NO118909B (de) | 1965-02-16 | 1966-02-15 |
Country Status (17)
| Country | Link |
|---|---|
| US (3) | US3489805A (de) |
| AT (1) | AT276852B (de) |
| BE (4) | BE676476A (de) |
| BR (2) | BR6677162D0 (de) |
| CH (2) | CH464600A (de) |
| DE (3) | DE1568744A1 (de) |
| DK (3) | DK123165B (de) |
| ES (1) | ES337469A1 (de) |
| FI (2) | FI45951C (de) |
| FR (4) | FR5407M (de) |
| GB (3) | GB1069350A (de) |
| IL (2) | IL25076A (de) |
| IT (3) | IT1053658B (de) |
| MY (2) | MY6800052A (de) |
| NL (5) | NL6601926A (de) |
| NO (2) | NO118909B (de) |
| SE (2) | SE346985B (de) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3524915A (en) * | 1968-09-16 | 1970-08-18 | Hoffmann La Roche | Synergistic insecticidal carbamates with 3,4 - methylenedioxyphenyl-3- halo-2-propynyl ethers |
| BE758735A (fr) * | 1969-11-14 | 1971-05-10 | Hoffmann La Roche | Composes acetyleniques |
| US3946040A (en) * | 1971-03-19 | 1976-03-23 | Hoffmann-La Roche Inc. | Propynyl benzyl ethers |
| US3880999A (en) * | 1971-07-20 | 1975-04-29 | Douglas J Hennessy | Synergistic insecticidal compositions containing benzyl 2-propynyl ethers |
| US3879421A (en) * | 1972-01-17 | 1975-04-22 | Stauffer Chemical Co | Certain methylenedioxyphenyl propynes |
| US4141921A (en) | 1972-02-09 | 1979-02-27 | Ciba-Geigy Corporation | Phenoxyphenyl- and phenoxybenzyl-alkynyl ethers |
| US4153731A (en) | 1973-04-18 | 1979-05-08 | Ciba-Geigy Corporation | Phenoxy (benzyloxy/benzylthio) benzene derivatives |
| US4020111A (en) * | 1973-09-13 | 1977-04-26 | Hennessy Douglas J | Propynyloxy alkyl arene insecticides |
| IT1059127B (it) * | 1976-04-15 | 1982-05-31 | Montedison Spa | Eteri e tioeteri benzilici o feni lici a catena alifatica lineare con terminale alogenato ad attivi ta ormonica giovanile e acaric/da |
| US4191773A (en) * | 1977-11-25 | 1980-03-04 | Hoffmann-La Roche Inc. | Synergistic insecticidal composition |
| JPH0749379B2 (ja) * | 1985-12-27 | 1995-05-31 | 住友化学工業株式会社 | 置換ベンゼン誘導体およびそれを有効成分とする農園芸用殺菌剤 |
| DE3800306A1 (de) * | 1988-01-08 | 1989-07-20 | Basf Ag | Tert.-butylalkinole, verfahren zu ihrer herstellung und deren verwendung |
| EP2289889A1 (de) * | 2009-08-18 | 2011-03-02 | Endura S.p.a. | Substituierte Alkynylphenoxy-Verbindungen und ihre Verwendungen |
| EP3141115A1 (de) | 2015-09-09 | 2017-03-15 | Endura S.p.a. | Substituierte methylendioxybenzyl verbindungen und ihre verwendungen as synergisten |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2942014A (en) * | 1955-12-07 | 1960-06-21 | Monsanto Chemicals | Oxidative coupling process |
| US2993934A (en) * | 1956-08-08 | 1961-07-25 | Diamond Alkali Co | Derivatives of pentachlorophenol |
| US3009855A (en) * | 1958-08-07 | 1961-11-21 | Union Carbide Corp | Method and composition of destroying insects employing 1-naphthyl n-methyl carbamate |
| US3322813A (en) * | 1962-06-30 | 1967-05-30 | Meiji Seika Kaisha | Halopropargyl aryl ether compounds |
-
1965
- 1965-09-08 US US485904A patent/US3489805A/en not_active Expired - Lifetime
- 1965-09-10 US US486545A patent/US3362871A/en not_active Expired - Lifetime
-
1966
- 1966-01-27 CH CH1146567A patent/CH464600A/de unknown
- 1966-01-29 DE DE19661568744 patent/DE1568744A1/de active Pending
- 1966-01-31 IL IL25076A patent/IL25076A/xx unknown
- 1966-02-11 GB GB6018/66A patent/GB1069350A/en not_active Expired
- 1966-02-14 FR FR49431A patent/FR5407M/fr not_active Expired
- 1966-02-15 NL NL6601926A patent/NL6601926A/xx unknown
- 1966-02-15 NO NO161707A patent/NO118909B/no unknown
- 1966-02-15 BE BE676476D patent/BE676476A/xx unknown
- 1966-02-16 DK DK81166AA patent/DK123165B/da unknown
- 1966-02-16 FI FI660383A patent/FI45951C/fi active
- 1966-02-16 SE SE02009/66A patent/SE346985B/xx unknown
- 1966-02-16 BR BR177162/66A patent/BR6677162D0/pt unknown
- 1966-02-16 IT IT3414/66A patent/IT1053658B/it active
- 1966-03-03 US US531371A patent/US3423428A/en not_active Expired - Lifetime
- 1966-08-23 DE DE19661568780 patent/DE1568780A1/de active Pending
- 1966-08-24 CH CH1223566A patent/CH477815A/de not_active IP Right Cessation
- 1966-08-26 AT AT809466A patent/AT276852B/de not_active IP Right Cessation
- 1966-08-26 DE DE19661542909 patent/DE1542909A1/de active Pending
- 1966-08-29 FR FR74427A patent/FR5694M/fr not_active Expired
- 1966-08-29 IL IL26400A patent/IL26400A/en unknown
- 1966-09-01 BR BR182528/66A patent/BR6682528D0/pt unknown
- 1966-09-02 FR FR75009A patent/FR1510861A/fr not_active Expired
- 1966-09-05 BE BE686416D patent/BE686416A/xx unknown
- 1966-09-05 BE BE686415D patent/BE686415A/xx unknown
- 1966-09-06 GB GB39689/66A patent/GB1102639A/en not_active Expired
- 1966-09-07 NO NO66164608A patent/NO116567B/no unknown
- 1966-09-08 NL NL6612645A patent/NL6612645A/xx unknown
- 1966-09-08 FI FI2343/66A patent/FI43797B/fi active
- 1966-09-08 IT IT20643/66A patent/IT986752B/it active
- 1966-09-08 SE SE12097/66A patent/SE360002B/xx unknown
- 1966-09-08 IT IT20649/66A patent/IT947002B/it active
- 1966-09-08 DK DK462366AA patent/DK116481B/da unknown
- 1966-09-08 NL NL6612647A patent/NL6612647A/xx unknown
- 1966-09-08 NL NL6612646A patent/NL6612646A/xx unknown
-
1967
- 1967-02-13 NL NL6702139A patent/NL6702139A/xx unknown
- 1967-02-22 GB GB8393/67A patent/GB1105848A/en not_active Expired
- 1967-02-28 BE BE694744D patent/BE694744A/xx unknown
- 1967-03-01 FR FR96924A patent/FR1512869A/fr not_active Expired
- 1967-03-02 ES ES337469A patent/ES337469A1/es not_active Expired
-
1968
- 1968-12-31 MY MY196852A patent/MY6800052A/xx unknown
-
1969
- 1969-06-06 DK DK306369AA patent/DK125239B/da unknown
- 1969-12-31 MY MY196968A patent/MY6900068A/xx unknown
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