FI64736C - Insektsattraherande komposition foer hannar av saedesbroddfly och foerfarande foer framstaellning av dess aktiva komponenter - Google Patents
Insektsattraherande komposition foer hannar av saedesbroddfly och foerfarande foer framstaellning av dess aktiva komponenter Download PDFInfo
- Publication number
- FI64736C FI64736C FI804017A FI804017A FI64736C FI 64736 C FI64736 C FI 64736C FI 804017 A FI804017 A FI 804017A FI 804017 A FI804017 A FI 804017A FI 64736 C FI64736 C FI 64736C
- Authority
- FI
- Finland
- Prior art keywords
- acetate
- formula
- compound
- dodeken
- general formula
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims description 40
- 238000000034 method Methods 0.000 claims description 39
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 34
- 150000001875 compounds Chemical class 0.000 claims description 32
- 239000004480 active ingredient Substances 0.000 claims description 17
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims description 16
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 14
- 238000002360 preparation method Methods 0.000 claims description 14
- -1 lithium aluminum hydride Chemical compound 0.000 claims description 12
- HGBOYTHUEUWSSQ-UHFFFAOYSA-N pentanal Chemical compound CCCCC=O HGBOYTHUEUWSSQ-UHFFFAOYSA-N 0.000 claims description 12
- 239000002904 solvent Substances 0.000 claims description 12
- 239000011541 reaction mixture Substances 0.000 claims description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 9
- 241000218475 Agrotis segetum Species 0.000 claims description 9
- 241000282472 Canis lupus familiaris Species 0.000 claims description 7
- 241000238631 Hexapoda Species 0.000 claims description 7
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 6
- 239000007788 liquid Substances 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- ALSTYHKOOCGGFT-KTKRTIGZSA-N (9Z)-octadecen-1-ol Chemical compound CCCCCCCC\C=C/CCCCCCCCO ALSTYHKOOCGGFT-KTKRTIGZSA-N 0.000 claims description 5
- 239000002775 capsule Substances 0.000 claims description 5
- ALSTYHKOOCGGFT-UHFFFAOYSA-N cis-oleyl alcohol Natural products CCCCCCCCC=CCCCCCCCCO ALSTYHKOOCGGFT-UHFFFAOYSA-N 0.000 claims description 5
- 239000012442 inert solvent Substances 0.000 claims description 5
- 230000013011 mating Effects 0.000 claims description 5
- 239000003960 organic solvent Substances 0.000 claims description 5
- 241000881711 Acipenser sturio Species 0.000 claims description 4
- 241000555745 Sciuridae Species 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 239000002418 insect attractant Substances 0.000 claims description 4
- 239000012280 lithium aluminium hydride Substances 0.000 claims description 4
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 3
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims description 3
- 230000021736 acetylation Effects 0.000 claims description 3
- 238000006640 acetylation reaction Methods 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 3
- KHIWWQKSHDUIBK-UHFFFAOYSA-N periodic acid Chemical compound OI(=O)(=O)=O KHIWWQKSHDUIBK-UHFFFAOYSA-N 0.000 claims description 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 2
- 239000012080 ambient air Substances 0.000 claims description 2
- 239000002131 composite material Substances 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims description 2
- 239000002516 radical scavenger Substances 0.000 claims description 2
- 239000012312 sodium hydride Substances 0.000 claims description 2
- 229910000104 sodium hydride Inorganic materials 0.000 claims description 2
- 239000012439 solid excipient Substances 0.000 claims description 2
- FAPGZYWJMFBPEU-UHFFFAOYSA-N 8-(3-octyloxiran-2-yl)octyl acetate Chemical compound CCCCCCCCC1OC1CCCCCCCCOC(C)=O FAPGZYWJMFBPEU-UHFFFAOYSA-N 0.000 claims 1
- 241000238017 Astacoidea Species 0.000 claims 1
- 125000006519 CCH3 Chemical group 0.000 claims 1
- 239000003586 protic polar solvent Substances 0.000 claims 1
- 229940095068 tetradecene Drugs 0.000 claims 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 36
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 11
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 10
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 10
- 239000003016 pheromone Substances 0.000 description 10
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 230000000694 effects Effects 0.000 description 9
- 239000013543 active substance Substances 0.000 description 7
- 239000003570 air Substances 0.000 description 6
- 239000005662 Paraffin oil Substances 0.000 description 5
- 241000607479 Yersinia pestis Species 0.000 description 5
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 5
- 235000019341 magnesium sulphate Nutrition 0.000 description 5
- 238000004949 mass spectrometry Methods 0.000 description 5
- 239000011780 sodium chloride Substances 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 239000012071 phase Substances 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000004698 Polyethylene Substances 0.000 description 3
- 239000000877 Sex Attractant Substances 0.000 description 3
- 235000019486 Sunflower oil Nutrition 0.000 description 3
- 239000005667 attractant Substances 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 239000012153 distilled water Substances 0.000 description 3
- 229920001971 elastomer Polymers 0.000 description 3
- 239000002917 insecticide Substances 0.000 description 3
- 229920000573 polyethylene Polymers 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 239000002600 sunflower oil Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- ZQSQIJOUWCCXAJ-UHFFFAOYSA-M (6-methoxy-6-oxohexyl)-triphenylphosphanium;bromide Chemical compound [Br-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(CCCCCC(=O)OC)C1=CC=CC=C1 ZQSQIJOUWCCXAJ-UHFFFAOYSA-M 0.000 description 2
- MTRYLAXNDGUFAK-UHFFFAOYSA-N 9-ethoxy-9-oxononanoic acid Chemical compound CCOC(=O)CCCCCCCC(O)=O MTRYLAXNDGUFAK-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 2
- 239000012346 acetyl chloride Substances 0.000 description 2
- 239000012300 argon atmosphere Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 230000031902 chemoattractant activity Effects 0.000 description 2
- 238000011109 contamination Methods 0.000 description 2
- DMEGYFMYUHOHGS-UHFFFAOYSA-N cycloheptane Chemical compound C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 2
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 2
- 230000007613 environmental effect Effects 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000012467 final product Substances 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 239000003292 glue Substances 0.000 description 2
- 238000005470 impregnation Methods 0.000 description 2
- 239000003350 kerosene Substances 0.000 description 2
- 230000000422 nocturnal effect Effects 0.000 description 2
- GYHFUZHODSMOHU-UHFFFAOYSA-N nonanal Chemical compound CCCCCCCCC=O GYHFUZHODSMOHU-UHFFFAOYSA-N 0.000 description 2
- 239000002420 orchard Substances 0.000 description 2
- 150000004714 phosphonium salts Chemical class 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 2
- 241000894007 species Species 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- WAEWJBWJSRGWFY-UHFFFAOYSA-N 2,3-dioctyloxirane Chemical compound CCCCCCCCC1OC1CCCCCCCC WAEWJBWJSRGWFY-UHFFFAOYSA-N 0.000 description 1
- HXGLPUATJSLAMX-UHFFFAOYSA-N 2-oct-7-enyl-3-octyloxirane Chemical compound CCCCCCCCC1OC1CCCCCCC=C HXGLPUATJSLAMX-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
- IGNBKLCFKTYIRI-UHFFFAOYSA-N 7-chloroheptanoic acid Chemical compound OC(=O)CCCCCCCl IGNBKLCFKTYIRI-UHFFFAOYSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- LIOHXTBHAXATAT-UHFFFAOYSA-N 9-oxononyl acetate Chemical compound CC(=O)OCCCCCCCCC=O LIOHXTBHAXATAT-UHFFFAOYSA-N 0.000 description 1
- 241000238421 Arthropoda Species 0.000 description 1
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 1
- 241000219310 Beta vulgaris subsp. vulgaris Species 0.000 description 1
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 1
- 241000282465 Canis Species 0.000 description 1
- GZZPOFFXKUVNSW-UHFFFAOYSA-N Dodecenoic acid Natural products OC(=O)CCCCCCCCCC=C GZZPOFFXKUVNSW-UHFFFAOYSA-N 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 241000272190 Falco peregrinus Species 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 244000061176 Nicotiana tabacum Species 0.000 description 1
- 235000002637 Nicotiana tabacum Nutrition 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical class OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 1
- 241000399256 Pteromyini Species 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
- 235000021536 Sugar beet Nutrition 0.000 description 1
- 241000287436 Turdus merula Species 0.000 description 1
- 241000251539 Vertebrata <Metazoa> Species 0.000 description 1
- 238000007239 Wittig reaction Methods 0.000 description 1
- LDPLIHVYUJTDKY-UHFFFAOYSA-N [O-]C(=O)CCCCC[P+](c1ccccc1)(c1ccccc1)c1ccccc1 Chemical compound [O-]C(=O)CCCCC[P+](c1ccccc1)(c1ccccc1)c1ccccc1 LDPLIHVYUJTDKY-UHFFFAOYSA-N 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 229960004217 benzyl alcohol Drugs 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 239000013065 commercial product Substances 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- 238000009429 electrical wiring Methods 0.000 description 1
- 150000002084 enol ethers Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 230000001976 improved effect Effects 0.000 description 1
- 230000000749 insecticidal effect Effects 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910052987 metal hydride Inorganic materials 0.000 description 1
- 150000004681 metal hydrides Chemical class 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 239000003094 microcapsule Substances 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 230000009965 odorless effect Effects 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 238000005949 ozonolysis reaction Methods 0.000 description 1
- VAUKWMSXUKODHR-UHFFFAOYSA-M pentyl(triphenyl)phosphanium;bromide Chemical compound [Br-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(CCCCC)C1=CC=CC=C1 VAUKWMSXUKODHR-UHFFFAOYSA-M 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000001850 reproductive effect Effects 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- WRIKHQLVHPKCJU-UHFFFAOYSA-N sodium bis(trimethylsilyl)amide Chemical compound C[Si](C)(C)N([Na])[Si](C)(C)C WRIKHQLVHPKCJU-UHFFFAOYSA-N 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000010265 sodium sulphite Nutrition 0.000 description 1
- 230000004936 stimulating effect Effects 0.000 description 1
- 239000011885 synergistic combination Substances 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 230000003442 weekly effect Effects 0.000 description 1
- 238000003466 welding Methods 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
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/02—Saturated carboxylic acids or thio analogues thereof; Derivatives thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
- C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
- C07C29/147—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of carboxylic acids or derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/08—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/28—Preparation of carboxylic acid esters by modifying the hydroxylic moiety of the ester, such modification not being an introduction of an ester group
- C07C67/293—Preparation of carboxylic acid esters by modifying the hydroxylic moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
- C07C67/333—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton
- C07C67/343—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/38—Compounds containing oxirane rings with hydrocarbon radicals, substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D303/40—Compounds containing oxirane rings with hydrocarbon radicals, substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals by ester radicals
- C07D303/42—Acyclic compounds having a chain of seven or more carbon atoms, e.g. epoxidised fats
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Dentistry (AREA)
- Engineering & Computer Science (AREA)
- Plant Pathology (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- General Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pain & Pain Management (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Rheumatology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU79EE2721A HU184622B (en) | 1979-12-29 | 1979-12-29 | Process for preparing 7/z/-dodecen-1-yl-acetate |
| HUEE002721 | 1979-12-29 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI804017L FI804017L (fi) | 1981-06-30 |
| FI64736B FI64736B (fi) | 1983-09-30 |
| FI64736C true FI64736C (fi) | 1984-01-10 |
Family
ID=10995885
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI804017A FI64736C (fi) | 1979-12-29 | 1980-12-23 | Insektsattraherande komposition foer hannar av saedesbroddfly och foerfarande foer framstaellning av dess aktiva komponenter |
Country Status (20)
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS57139005A (en) * | 1981-02-19 | 1982-08-27 | Otsuka Pharmaceut Co Ltd | Composition disturbing communication between insect pests |
| HU187779B (en) * | 1982-08-10 | 1986-02-28 | Egyt Gyogyszervegyeszeti Gyar,Hu | Composition for enticing turnip moth males |
| GR860221B (en) * | 1985-02-15 | 1986-05-22 | Basf Ag | Vineyards insecticidal means and method therefor |
| US4837358A (en) * | 1986-02-26 | 1989-06-06 | Phillips Petroleum Company | Preparation of 9-alkenyl ester compounds |
| US4696676A (en) * | 1986-06-27 | 1987-09-29 | International Flavors & Fragrances Inc. | Use of 1-nonen-3-ol for repelling insects |
| US4693890A (en) * | 1986-06-27 | 1987-09-15 | International Flavors & Fragrances Inc. | Use of 1-nonen-3-ol for repelling insects |
| US4759228A (en) * | 1987-01-09 | 1988-07-26 | International Flavors & Fragrances Inc. | Process for determination of repellency and attractancy |
| US4940831A (en) * | 1989-02-15 | 1990-07-10 | Phillips Petroleum Company | Purification of cis-olefins |
| WO1992009199A1 (en) * | 1990-11-23 | 1992-06-11 | Kansas State University Research Foundation | Method of attracting male hessian flies |
| CN107836450A (zh) * | 2017-11-06 | 2018-03-27 | 中国农业科学院植物保护研究所 | 一种大地老虎性诱剂的制备方法及应用 |
-
1978
- 1978-12-28 SU SU782893651A patent/SU999973A3/ru active
-
1979
- 1979-12-29 HU HU79EE2721A patent/HU184622B/hu unknown
-
1980
- 1980-12-18 DD DD80226261A patent/DD155383A5/de unknown
- 1980-12-18 SE SE8008943A patent/SE8008943L/xx not_active Application Discontinuation
- 1980-12-22 NL NL8006957A patent/NL8006957A/nl not_active Application Discontinuation
- 1980-12-22 BE BE1/10086A patent/BE886800A/fr not_active IP Right Cessation
- 1980-12-22 CS CS809198A patent/CS226420B2/cs unknown
- 1980-12-23 FI FI804017A patent/FI64736C/fi not_active IP Right Cessation
- 1980-12-23 DK DK553780A patent/DK553780A/da not_active Application Discontinuation
- 1980-12-23 FR FR8027288A patent/FR2472340A1/fr active Granted
- 1980-12-24 US US06/220,113 patent/US4364931A/en not_active Expired - Lifetime
- 1980-12-24 CH CH956580A patent/CH646034A5/de not_active IP Right Cessation
- 1980-12-24 ES ES498615A patent/ES8205744A1/es not_active Expired
- 1980-12-29 DE DE19803049309 patent/DE3049309A1/de not_active Withdrawn
- 1980-12-29 IT IT8026979A patent/IT1195200B/it active
- 1980-12-29 GB GB8041437A patent/GB2066666B/en not_active Expired
- 1980-12-29 PL PL1980228812A patent/PL127039B1/pl unknown
- 1980-12-29 JP JP18941480A patent/JPS56100701A/ja active Pending
- 1980-12-29 CA CA000367601A patent/CA1167763A/en not_active Expired
- 1980-12-29 AT AT0632280A patent/AT367600B/de not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| PL127039B1 (en) | 1983-09-30 |
| PL228812A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1981-12-11 |
| FI804017L (fi) | 1981-06-30 |
| GB2066666A (en) | 1981-07-15 |
| HU184622B (en) | 1984-09-28 |
| GB2066666B (en) | 1983-08-17 |
| FR2472340A1 (fr) | 1981-07-03 |
| ES498615A0 (es) | 1982-07-01 |
| IT8026979A0 (it) | 1980-12-29 |
| ES8205744A1 (es) | 1982-07-01 |
| SE8008943L (sv) | 1981-06-30 |
| SU999973A3 (ru) | 1983-02-23 |
| CH646034A5 (de) | 1984-11-15 |
| BE886800A (fr) | 1981-06-22 |
| CA1167763A (en) | 1984-05-22 |
| FR2472340B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1984-01-27 |
| CS226420B2 (en) | 1984-03-19 |
| ATA632280A (de) | 1981-12-15 |
| DD155383A5 (de) | 1982-06-09 |
| IT1195200B (it) | 1988-10-12 |
| JPS56100701A (en) | 1981-08-12 |
| US4364931A (en) | 1982-12-21 |
| AT367600B (de) | 1982-07-12 |
| NL8006957A (nl) | 1981-08-03 |
| DE3049309A1 (de) | 1981-09-17 |
| FI64736B (fi) | 1983-09-30 |
| DK553780A (da) | 1981-06-30 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US4455441A (en) | Attractant termiticidal compounds, compositions and methods of use therefor | |
| FI64736C (fi) | Insektsattraherande komposition foer hannar av saedesbroddfly och foerfarande foer framstaellning av dess aktiva komponenter | |
| US6207705B1 (en) | Biopesticides related to natural sources | |
| US3636059A (en) | Cyclopentenolone esters | |
| US4075320A (en) | Attractant for ants | |
| US3515730A (en) | Thenyl esters of cyclopropanecarboxylic acids | |
| US4243660A (en) | Composite insect attractant for male cabbage moths and a process for preparing its active agents | |
| US3586712A (en) | Attractant for pink bollworm moths | |
| SU586821A3 (ru) | Способ борьбы с насекомыми и клещами | |
| US3702358A (en) | Cis - 1 - hexadecen-1-ol acetate as an attractant for adult male pink bollworm moths | |
| CA1160240A (en) | 2,3-dihydropyrans, processes for their preparation, and methods for combatting insects therewith | |
| US5053223A (en) | Process and agents for control of white coffee-leaf miners, especially perileucoptera coffeella | |
| FR2570704A1 (fr) | Nouveaux n-alkyl(ene)-n-(o,o-disubstitue-thiophosphoryl)-n',n'-disubstitue-glycine-amides, procede pour leur preparation et acaricide, insecticide et fongicide contenant ces composes comme substance active | |
| US2886485A (en) | 6-bromopiperonyl and 6-chloropiperonyl esters of chrysanthemumic acid as insecticides | |
| US2579299A (en) | Chlorinated isobornyl chloride insecticidal composition | |
| RU1396516C (ru) | Феромон дл листовертки узкокрылой изменчивой CNEPHASIA CHRYSANTHEANA DUP | |
| US4200590A (en) | (6E,10Z)-3,4,7,11-Tetramethyl-6,10-tridecadienal-1 | |
| JP3128592B2 (ja) | ワタヘリクロノメイガの性誘引剤 | |
| JPH02243606A (ja) | ５―テトラデセン酸メチルを有効成分とする昆虫誘引剤 | |
| KR830001227B1 (ko) | 조 밤나방의 성유인 조성물 | |
| US3742097A (en) | Process for preparing diadducts of hydrocarbylthiophosphoric acids | |
| GB1600486A (en) | Long chain unsaturated aldehyde useful as a trailfollowing substances | |
| BE897484A (fr) | Produit composite attirant des insectes, pour les papillons a y-argentes males | |
| SU199783A1 (ru) | Способ получения инсектицидных эфиров хризантемовой или пиретровой кислоты | |
| JPS5998007A (ja) | 昆虫誘引剤 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM | Patent lapsed |
Owner name: E GY T GYOGYSZERVEGYESZETI GYAR |