NO811241L - Nye terpenderivater, fremgangsmaate ved fremstilling av disse derivater og insekticid middel inneholdende disse - Google Patents
Nye terpenderivater, fremgangsmaate ved fremstilling av disse derivater og insekticid middel inneholdende disseInfo
- Publication number
- NO811241L NO811241L NO811241A NO811241A NO811241L NO 811241 L NO811241 L NO 811241L NO 811241 A NO811241 A NO 811241A NO 811241 A NO811241 A NO 811241A NO 811241 L NO811241 L NO 811241L
- Authority
- NO
- Norway
- Prior art keywords
- general formula
- preparation
- compounds
- oxo
- compound
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 title claims description 56
- 238000000034 method Methods 0.000 title claims description 21
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 50
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 17
- 239000001257 hydrogen Substances 0.000 claims abstract description 17
- 239000004480 active ingredient Substances 0.000 claims abstract description 14
- 239000002917 insecticide Substances 0.000 claims abstract description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 10
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 7
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 6
- 239000001301 oxygen Substances 0.000 claims abstract description 6
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 6
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims abstract description 4
- 150000002431 hydrogen Chemical group 0.000 claims abstract description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract 2
- 150000001875 compounds Chemical class 0.000 claims description 86
- 150000003505 terpenes Chemical class 0.000 claims description 12
- 235000007586 terpenes Nutrition 0.000 claims description 12
- -1 cyclopentanonyl group Chemical group 0.000 claims description 11
- 239000002253 acid Substances 0.000 claims description 10
- 230000003197 catalytic effect Effects 0.000 claims description 5
- 150000001861 citronellal derivatives Chemical class 0.000 claims description 5
- 238000003379 elimination reaction Methods 0.000 claims description 5
- HNPPYGKOZVDFPP-UHFFFAOYSA-N ethyl 5-hydroxy-11-methoxy-7,11-dimethyl-3-oxododecanoate Chemical group CCOC(=O)CC(=O)CC(O)CC(C)CCCC(C)(C)OC HNPPYGKOZVDFPP-UHFFFAOYSA-N 0.000 claims description 5
- 229910000102 alkali metal hydride Inorganic materials 0.000 claims description 4
- 150000008046 alkali metal hydrides Chemical class 0.000 claims description 4
- 239000003085 diluting agent Substances 0.000 claims description 3
- 239000002949 juvenile hormone Substances 0.000 claims description 3
- ZNANBQGHTXLKGD-UHFFFAOYSA-N propan-2-yl 5-hydroxy-11-methoxy-7,11-dimethyl-3-oxododecanoate Chemical compound COC(C)(C)CCCC(C)CC(O)CC(=O)CC(=O)OC(C)C ZNANBQGHTXLKGD-UHFFFAOYSA-N 0.000 claims description 3
- 125000001539 acetonyl group Chemical group [H]C([H])([H])C(=O)C([H])([H])* 0.000 claims description 2
- 239000000654 additive Substances 0.000 claims description 2
- JTVKJQZXVDOQSU-UHFFFAOYSA-N tert-butyl 5-hydroxy-11-methoxy-7,11-dimethyl-3-oxododecanoate Chemical compound COC(C)(C)CCCC(C)CC(O)CC(=O)CC(=O)OC(C)(C)C JTVKJQZXVDOQSU-UHFFFAOYSA-N 0.000 claims description 2
- 239000012050 conventional carrier Substances 0.000 claims 1
- PAWGRNGPMLVJQH-ZHACJKMWSA-N trans-2-dodecenoic acid Chemical compound CCCCCCCCC\C=C\C(O)=O PAWGRNGPMLVJQH-ZHACJKMWSA-N 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 abstract description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract description 3
- 241000779819 Syncarpia glomulifera Species 0.000 abstract 2
- 239000001739 pinus spp. Substances 0.000 abstract 2
- 229940036248 turpentine Drugs 0.000 abstract 2
- 239000000243 solution Substances 0.000 description 68
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 47
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 40
- 239000011541 reaction mixture Substances 0.000 description 39
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 38
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 37
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 28
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
- 239000002904 solvent Substances 0.000 description 26
- 239000000203 mixture Substances 0.000 description 25
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
- 238000004440 column chromatography Methods 0.000 description 23
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 21
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 21
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 21
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 20
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 20
- 238000004458 analytical method Methods 0.000 description 18
- 230000002829 reductive effect Effects 0.000 description 18
- 239000003795 chemical substances by application Substances 0.000 description 17
- 239000011780 sodium chloride Substances 0.000 description 17
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 14
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 13
- 241000238631 Hexapoda Species 0.000 description 11
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 11
- 229910000104 sodium hydride Inorganic materials 0.000 description 11
- 239000012312 sodium hydride Substances 0.000 description 11
- 239000000839 emulsion Substances 0.000 description 10
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 10
- 235000019341 magnesium sulphate Nutrition 0.000 description 10
- 239000003921 oil Substances 0.000 description 10
- 235000019198 oils Nutrition 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- 239000000725 suspension Substances 0.000 description 10
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 9
- 229960004217 benzyl alcohol Drugs 0.000 description 9
- 239000000284 extract Substances 0.000 description 9
- 239000004533 oil dispersion Substances 0.000 description 9
- 239000000126 substance Substances 0.000 description 9
- WRMNZCZEMHIOCP-UHFFFAOYSA-N 2-phenylethanol Chemical compound OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 description 8
- 239000012300 argon atmosphere Substances 0.000 description 8
- IDWULKZGRNHZNR-UHFFFAOYSA-N 7-methoxy-3,7-dimethyloctanal Chemical compound COC(C)(C)CCCC(C)CC=O IDWULKZGRNHZNR-UHFFFAOYSA-N 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
- 238000002474 experimental method Methods 0.000 description 7
- 239000008187 granular material Substances 0.000 description 7
- 239000007921 spray Substances 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- 239000012141 concentrate Substances 0.000 description 6
- 235000008504 concentrate Nutrition 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 5
- TXHIDIHEXDFONW-UHFFFAOYSA-N benzene;propan-2-one Chemical compound CC(C)=O.C1=CC=CC=C1 TXHIDIHEXDFONW-UHFFFAOYSA-N 0.000 description 5
- 239000000969 carrier Substances 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 238000011161 development Methods 0.000 description 5
- 230000018109 developmental process Effects 0.000 description 5
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 5
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 5
- 229910052500 inorganic mineral Inorganic materials 0.000 description 5
- 239000010410 layer Substances 0.000 description 5
- 235000010755 mineral Nutrition 0.000 description 5
- GVIIRWAJDFKJMJ-UHFFFAOYSA-N propan-2-yl 3-oxobutanoate Chemical compound CC(C)OC(=O)CC(C)=O GVIIRWAJDFKJMJ-UHFFFAOYSA-N 0.000 description 5
- 229920006395 saturated elastomer Polymers 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 239000000314 lubricant Substances 0.000 description 4
- DVSDBMFJEQPWNO-UHFFFAOYSA-N methyllithium Chemical compound C[Li] DVSDBMFJEQPWNO-UHFFFAOYSA-N 0.000 description 4
- 239000011707 mineral Substances 0.000 description 4
- 159000000000 sodium salts Chemical class 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- OMQHDIHZSDEIFH-UHFFFAOYSA-N 3-Acetyldihydro-2(3H)-furanone Chemical compound CC(=O)C1CCOC1=O OMQHDIHZSDEIFH-UHFFFAOYSA-N 0.000 description 3
- JZQLNAXBRXIMAI-UHFFFAOYSA-N 4-(3-hydroxy-9-methoxy-5,9-dimethyldecanoyl)oxolan-2-one Chemical compound COC(C)(C)CCCC(C)CC(O)CC(=O)C1COC(=O)C1 JZQLNAXBRXIMAI-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000003463 adsorbent Substances 0.000 description 3
- KSTSKZBJCVLLKS-UHFFFAOYSA-N benzene;propan-2-ol Chemical compound CC(C)O.C1=CC=CC=C1 KSTSKZBJCVLLKS-UHFFFAOYSA-N 0.000 description 3
- 235000014113 dietary fatty acids Nutrition 0.000 description 3
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
- 239000002270 dispersing agent Substances 0.000 description 3
- 239000003995 emulsifying agent Substances 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 239000000194 fatty acid Substances 0.000 description 3
- 229930195729 fatty acid Natural products 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- VVNXEADCOVSAER-UHFFFAOYSA-N lithium sodium Chemical compound [Li].[Na] VVNXEADCOVSAER-UHFFFAOYSA-N 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 239000002689 soil Substances 0.000 description 3
- 239000004094 surface-active agent Substances 0.000 description 3
- 239000000375 suspending agent Substances 0.000 description 3
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 2
- 239000001266 2,3-dihydroxypropyl 3-oxododecanoate Substances 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- 239000005995 Aluminium silicate Substances 0.000 description 2
- 240000007124 Brassica oleracea Species 0.000 description 2
- 235000003899 Brassica oleracea var acephala Nutrition 0.000 description 2
- 235000011301 Brassica oleracea var capitata Nutrition 0.000 description 2
- 235000001169 Brassica oleracea var oleracea Nutrition 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- 241000196324 Embryophyta Species 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 241000255969 Pieris brassicae Species 0.000 description 2
- 241000382353 Pupa Species 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 239000000853 adhesive Substances 0.000 description 2
- 230000001070 adhesive effect Effects 0.000 description 2
- 239000000443 aerosol Substances 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 235000012211 aluminium silicate Nutrition 0.000 description 2
- 125000000129 anionic group Chemical group 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- RTEXIPZMMDUXMR-UHFFFAOYSA-N benzene;ethyl acetate Chemical compound CCOC(C)=O.C1=CC=CC=C1 RTEXIPZMMDUXMR-UHFFFAOYSA-N 0.000 description 2
- MDHYEMXUFSJLGV-UHFFFAOYSA-N beta-phenethyl acetate Natural products CC(=O)OCCC1=CC=CC=C1 MDHYEMXUFSJLGV-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 239000001913 cellulose Substances 0.000 description 2
- 229920002678 cellulose Polymers 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- NEHNMFOYXAPHSD-UHFFFAOYSA-N citronellal Chemical compound O=CCC(C)CCC=C(C)C NEHNMFOYXAPHSD-UHFFFAOYSA-N 0.000 description 2
- 239000004927 clay Substances 0.000 description 2
- 238000012937 correction Methods 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- SWXVUIWOUIDPGS-UHFFFAOYSA-N diacetone alcohol Chemical compound CC(=O)CC(C)(C)O SWXVUIWOUIDPGS-UHFFFAOYSA-N 0.000 description 2
- 125000005265 dialkylamine group Chemical group 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- FPRRTKZIOOBMJU-UHFFFAOYSA-N ethyl 5-hydroxy-7,11-dimethyl-3-oxododecanoate Chemical compound CCOC(=O)CC(=O)CC(O)CC(C)CCCC(C)C FPRRTKZIOOBMJU-UHFFFAOYSA-N 0.000 description 2
- XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 description 2
- 150000004665 fatty acids Chemical class 0.000 description 2
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 2
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 229910052744 lithium Inorganic materials 0.000 description 2
- 150000002642 lithium compounds Chemical class 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 239000002480 mineral oil Substances 0.000 description 2
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 230000036961 partial effect Effects 0.000 description 2
- 230000035515 penetration Effects 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 238000003825 pressing Methods 0.000 description 2
- CCRLXHZFPQPXOQ-UHFFFAOYSA-N propan-2-yl 5-hydroxy-7,11-dimethyl-3-oxododecanoate Chemical compound CC(C)CCCC(C)CC(O)CC(=O)CC(=O)OC(C)C CCRLXHZFPQPXOQ-UHFFFAOYSA-N 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 239000012266 salt solution Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 239000000454 talc Substances 0.000 description 2
- 229910052623 talc Inorganic materials 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 230000000699 topical effect Effects 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- UCSIFMPORANABL-SNVBAGLBSA-N (3r)-3,7-dimethyloctanal Chemical compound CC(C)CCC[C@@H](C)CC=O UCSIFMPORANABL-SNVBAGLBSA-N 0.000 description 1
- ALSTYHKOOCGGFT-KTKRTIGZSA-N (9Z)-octadecen-1-ol Chemical compound CCCCCCCC\C=C/CCCCCCCCO ALSTYHKOOCGGFT-KTKRTIGZSA-N 0.000 description 1
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- QGLWBTPVKHMVHM-KTKRTIGZSA-N (z)-octadec-9-en-1-amine Chemical compound CCCCCCCC\C=C/CCCCCCCCN QGLWBTPVKHMVHM-KTKRTIGZSA-N 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- KYCZRSVIJUQOAJ-UHFFFAOYSA-N 1-butylnaphthalene;sulfuric acid Chemical compound OS(O)(=O)=O.C1=CC=C2C(CCCC)=CC=CC2=C1 KYCZRSVIJUQOAJ-UHFFFAOYSA-N 0.000 description 1
- QAQSNXHKHKONNS-UHFFFAOYSA-N 1-ethyl-2-hydroxy-4-methyl-6-oxopyridine-3-carboxamide Chemical compound CCN1C(O)=C(C(N)=O)C(C)=CC1=O QAQSNXHKHKONNS-UHFFFAOYSA-N 0.000 description 1
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 1
- ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 2,3-dimethylbutane Chemical group CC(C)C(C)C ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 0.000 description 1
- CBQDTCDOVVBGMN-UHFFFAOYSA-N 2-methyl-3-octylphenol Chemical compound CCCCCCCCC1=CC=CC(O)=C1C CBQDTCDOVVBGMN-UHFFFAOYSA-N 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- UCSIFMPORANABL-UHFFFAOYSA-N 3,7-dimethyloctanal Chemical compound CC(C)CCCC(C)CC=O UCSIFMPORANABL-UHFFFAOYSA-N 0.000 description 1
- BTXXTMOWISPQSJ-UHFFFAOYSA-N 4,4,4-trifluorobutan-2-one Chemical class CC(=O)CC(F)(F)F BTXXTMOWISPQSJ-UHFFFAOYSA-N 0.000 description 1
- MKYBQIZDMIHLOK-VYPFIWODSA-N 4-[(e)-1,9-dimethoxy-5,9-dimethyldec-2-enylidene]oxolan-2-one Chemical compound COC(C)(C)CCCC(C)C/C=C/C(OC)=C1COC(=O)C1 MKYBQIZDMIHLOK-VYPFIWODSA-N 0.000 description 1
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- JDAURTQTYLOMSZ-WEVVVXLNSA-N 4-[(e)-9-methoxy-5,9-dimethyldec-2-enoyl]oxolan-2-one Chemical compound COC(C)(C)CCCC(C)C\C=C\C(=O)C1COC(=O)C1 JDAURTQTYLOMSZ-WEVVVXLNSA-N 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/26—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D307/30—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member 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 ring carbon atoms
- C07D307/32—Oxygen atoms
- C07D307/33—Oxygen atoms in position 2, the oxygen atom being in its keto or unsubstituted enol form
-
- 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
- A01N49/00—Biocides, pest repellants or attractants, or plant growth regulators, containing compounds containing the group, wherein m+n>=1, both X together may also mean —Y— or a direct carbon-to-carbon bond, and the carbon atoms marked with an asterisk are not part of any ring system other than that which may be formed by the atoms X, the carbon atoms in square brackets being part of any acyclic or cyclic structure, or the group, wherein A means a carbon atom or Y, n>=0, and not more than one of these carbon atoms being a member of the same ring system, e.g. juvenile insect hormones or mimics thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three 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, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D307/58—One oxygen atom, e.g. butenolide
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Plant Pathology (AREA)
- Zoology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Pest Control & Pesticides (AREA)
- Environmental Sciences (AREA)
- Insects & Arthropods (AREA)
- Agronomy & Crop Science (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Furan Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU8080877A HU180575B (en) | 1980-04-11 | 1980-04-11 | Insecticide compositions containing terpene derivatives and process for producing the terpene derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO811241L true NO811241L (no) | 1981-10-12 |
Family
ID=10951837
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO811241A NO811241L (no) | 1980-04-11 | 1981-04-10 | Nye terpenderivater, fremgangsmaate ved fremstilling av disse derivater og insekticid middel inneholdende disse |
Country Status (20)
| Country | Link |
|---|---|
| US (1) | US4344959A (de) |
| JP (1) | JPS579738A (de) |
| BE (1) | BE888360A (de) |
| CA (1) | CA1177838A (de) |
| DD (2) | DD158081A5 (de) |
| DE (1) | DE3114686A1 (de) |
| DK (1) | DK164881A (de) |
| ES (1) | ES501709A0 (de) |
| FI (1) | FI811120L (de) |
| FR (1) | FR2480278A1 (de) |
| GB (1) | GB2074570B (de) |
| GR (1) | GR74869B (de) |
| HU (1) | HU180575B (de) |
| IL (1) | IL62628A0 (de) |
| IT (1) | IT1211020B (de) |
| NL (1) | NL8101771A (de) |
| NO (1) | NO811241L (de) |
| PL (1) | PL126745B1 (de) |
| SE (1) | SE8102331L (de) |
| YU (1) | YU90181A (de) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5066482A (en) * | 1985-05-13 | 1991-11-19 | Sandoz Ltd. | Compositions and method for controlling cockroaches |
| CN112961127B (zh) * | 2021-02-05 | 2022-12-06 | 云南省烟草公司玉溪市公司 | 一种烟草源活性萜类化合物、制备方法及其应用 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2085652B1 (de) * | 1970-04-30 | 1973-08-10 | Roussel Uclaf | |
| US3700694A (en) * | 1971-06-14 | 1972-10-24 | Zoecon Corp | Insect control |
| US4010170A (en) * | 1975-09-24 | 1977-03-01 | Iowa State University Research Foundation, Inc. | Butenolide synthesis via carbonylation of vinylmercurials |
-
1980
- 1980-04-11 HU HU8080877A patent/HU180575B/hu not_active IP Right Cessation
-
1981
- 1981-04-06 US US06/251,043 patent/US4344959A/en not_active Expired - Fee Related
- 1981-04-07 YU YU00901/81A patent/YU90181A/xx unknown
- 1981-04-09 GB GB8111213A patent/GB2074570B/en not_active Expired
- 1981-04-09 GR GR64653A patent/GR74869B/el unknown
- 1981-04-10 IT IT8121029A patent/IT1211020B/it active
- 1981-04-10 IL IL62628A patent/IL62628A0/xx unknown
- 1981-04-10 ES ES501709A patent/ES501709A0/es active Granted
- 1981-04-10 SE SE8102331A patent/SE8102331L/xx not_active Application Discontinuation
- 1981-04-10 PL PL1981230620A patent/PL126745B1/pl unknown
- 1981-04-10 DD DD81229150A patent/DD158081A5/de not_active IP Right Cessation
- 1981-04-10 CA CA000375204A patent/CA1177838A/en not_active Expired
- 1981-04-10 FR FR8107212A patent/FR2480278A1/fr active Granted
- 1981-04-10 JP JP5306981A patent/JPS579738A/ja active Pending
- 1981-04-10 BE BE1/10200A patent/BE888360A/fr not_active IP Right Cessation
- 1981-04-10 NO NO811241A patent/NO811241L/no unknown
- 1981-04-10 DK DK164881A patent/DK164881A/da not_active Application Discontinuation
- 1981-04-10 NL NL8101771A patent/NL8101771A/nl not_active Application Discontinuation
- 1981-04-10 FI FI811120A patent/FI811120L/fi not_active Application Discontinuation
- 1981-04-10 DD DD81233715A patent/DD202000A5/de not_active IP Right Cessation
- 1981-04-10 DE DE3114686A patent/DE3114686A1/de not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| NL8101771A (nl) | 1981-11-02 |
| ES8307707A1 (es) | 1983-08-01 |
| FR2480278A1 (fr) | 1981-10-16 |
| DE3114686A1 (de) | 1982-01-14 |
| PL230620A1 (de) | 1982-03-29 |
| GB2074570B (en) | 1984-04-18 |
| DD158081A5 (de) | 1982-12-29 |
| GR74869B (de) | 1984-07-12 |
| YU90181A (en) | 1983-10-31 |
| DK164881A (da) | 1981-10-12 |
| PL126745B1 (en) | 1983-08-31 |
| FI811120L (fi) | 1981-10-12 |
| US4344959A (en) | 1982-08-17 |
| BE888360A (fr) | 1981-10-12 |
| IT8121029A0 (it) | 1981-04-10 |
| SE8102331L (sv) | 1981-10-12 |
| DD202000A5 (de) | 1983-08-24 |
| IT1211020B (it) | 1989-09-29 |
| CA1177838A (en) | 1984-11-13 |
| FR2480278B1 (de) | 1984-12-14 |
| IL62628A0 (en) | 1981-06-29 |
| HU180575B (en) | 1983-03-28 |
| JPS579738A (en) | 1982-01-19 |
| ES501709A0 (es) | 1983-08-01 |
| GB2074570A (en) | 1981-11-04 |
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