AU2003214243B2 - Dihydronepetalactone as insect repellent - Google Patents
Dihydronepetalactone as insect repellent Download PDFInfo
- Publication number
- AU2003214243B2 AU2003214243B2 AU2003214243A AU2003214243A AU2003214243B2 AU 2003214243 B2 AU2003214243 B2 AU 2003214243B2 AU 2003214243 A AU2003214243 A AU 2003214243A AU 2003214243 A AU2003214243 A AU 2003214243A AU 2003214243 B2 AU2003214243 B2 AU 2003214243B2
- Authority
- AU
- Australia
- Prior art keywords
- oil
- dihydronepetalactone
- insect
- host
- repellent
- 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.)
- Ceased
Links
- LSRNBGXEEKNZHN-UHFFFAOYSA-N Dihydronepetalactone Chemical compound O=C1OCC(C)C2C1C(C)CC2 LSRNBGXEEKNZHN-UHFFFAOYSA-N 0.000 title claims description 138
- 239000000077 insect repellent Substances 0.000 title claims description 79
- 239000000203 mixture Substances 0.000 claims description 123
- 241000238631 Hexapoda Species 0.000 claims description 65
- 239000003921 oil Substances 0.000 claims description 48
- 235000019198 oils Nutrition 0.000 claims description 48
- 150000001875 compounds Chemical class 0.000 claims description 34
- 241000255925 Diptera Species 0.000 claims description 30
- 238000000034 method Methods 0.000 claims description 30
- -1 dihydronepetalactone compound Chemical class 0.000 claims description 23
- 239000004480 active ingredient Substances 0.000 claims description 22
- 239000003205 fragrance Substances 0.000 claims description 17
- 239000007787 solid Substances 0.000 claims description 13
- 229920000642 polymer Polymers 0.000 claims description 8
- 239000007921 spray Substances 0.000 claims description 8
- 241000282414 Homo sapiens Species 0.000 claims description 7
- 241001465754 Metazoa Species 0.000 claims description 7
- 239000000499 gel Substances 0.000 claims description 7
- 102000004169 proteins and genes Human genes 0.000 claims description 7
- 108090000623 proteins and genes Proteins 0.000 claims description 7
- XMGQYMWWDOXHJM-UHFFFAOYSA-N limonene Chemical compound CC(=C)C1CCC(C)=CC1 XMGQYMWWDOXHJM-UHFFFAOYSA-N 0.000 claims description 6
- OSWPMRLSEDHDFF-UHFFFAOYSA-N methyl salicylate Chemical compound COC(=O)C1=CC=CC=C1O OSWPMRLSEDHDFF-UHFFFAOYSA-N 0.000 claims description 6
- 230000001846 repelling effect Effects 0.000 claims description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 6
- 239000004166 Lanolin Substances 0.000 claims description 4
- 241001674048 Phthiraptera Species 0.000 claims description 4
- 239000002671 adjuvant Substances 0.000 claims description 4
- 239000010632 citronella oil Substances 0.000 claims description 4
- NEHNMFOYXAPHSD-UHFFFAOYSA-N citronellal Chemical compound O=CCC(C)CCC=C(C)C NEHNMFOYXAPHSD-UHFFFAOYSA-N 0.000 claims description 4
- QMVPMAAFGQKVCJ-UHFFFAOYSA-N citronellol Chemical compound OCCC(C)CCC=C(C)C QMVPMAAFGQKVCJ-UHFFFAOYSA-N 0.000 claims description 4
- 229940039717 lanolin Drugs 0.000 claims description 4
- 235000019388 lanolin Nutrition 0.000 claims description 4
- ZMQAAUBTXCXRIC-UHFFFAOYSA-N safrole Chemical compound C=CCC1=CC=C2OCOC2=C1 ZMQAAUBTXCXRIC-UHFFFAOYSA-N 0.000 claims description 4
- 239000000344 soap Substances 0.000 claims description 4
- 241000258242 Siphonaptera Species 0.000 claims description 3
- 241000331598 Trombiculidae Species 0.000 claims description 3
- 239000003963 antioxidant agent Substances 0.000 claims description 3
- 235000006708 antioxidants Nutrition 0.000 claims description 3
- 239000004927 clay Substances 0.000 claims description 3
- 239000006071 cream Substances 0.000 claims description 3
- 239000006260 foam Substances 0.000 claims description 3
- 239000006210 lotion Substances 0.000 claims description 3
- 239000002674 ointment Substances 0.000 claims description 3
- 239000003381 stabilizer Substances 0.000 claims description 3
- NOOLISFMXDJSKH-UTLUCORTSA-N (+)-Neomenthol Chemical compound CC(C)[C@@H]1CC[C@@H](C)C[C@@H]1O NOOLISFMXDJSKH-UTLUCORTSA-N 0.000 claims description 2
- QMVPMAAFGQKVCJ-SNVBAGLBSA-N (R)-(+)-citronellol Natural products OCC[C@H](C)CCC=C(C)C QMVPMAAFGQKVCJ-SNVBAGLBSA-N 0.000 claims description 2
- 235000002961 Aloe barbadensis Nutrition 0.000 claims description 2
- 244000144927 Aloe barbadensis Species 0.000 claims description 2
- 244000144725 Amygdalus communis Species 0.000 claims description 2
- 235000011437 Amygdalus communis Nutrition 0.000 claims description 2
- 240000007087 Apium graveolens Species 0.000 claims description 2
- 235000015849 Apium graveolens Dulce Group Nutrition 0.000 claims description 2
- 235000010591 Appio Nutrition 0.000 claims description 2
- 235000002566 Capsicum Nutrition 0.000 claims description 2
- 235000005747 Carum carvi Nutrition 0.000 claims description 2
- 240000000467 Carum carvi Species 0.000 claims description 2
- 235000005976 Citrus sinensis Nutrition 0.000 claims description 2
- 240000002319 Citrus sinensis Species 0.000 claims description 2
- 235000007129 Cuminum cyminum Nutrition 0.000 claims description 2
- 244000304337 Cuminum cyminum Species 0.000 claims description 2
- NOOLISFMXDJSKH-UHFFFAOYSA-N DL-menthol Natural products CC(C)C1CCC(C)CC1O NOOLISFMXDJSKH-UHFFFAOYSA-N 0.000 claims description 2
- 240000002943 Elettaria cardamomum Species 0.000 claims description 2
- GYCKQBWUSACYIF-UHFFFAOYSA-N Ethyl salicylate Chemical compound CCOC(=O)C1=CC=CC=C1O GYCKQBWUSACYIF-UHFFFAOYSA-N 0.000 claims description 2
- 235000019501 Lemon oil Nutrition 0.000 claims description 2
- 235000006679 Mentha X verticillata Nutrition 0.000 claims description 2
- 235000002899 Mentha suaveolens Nutrition 0.000 claims description 2
- 235000001636 Mentha x rotundifolia Nutrition 0.000 claims description 2
- 239000006002 Pepper Substances 0.000 claims description 2
- 235000016761 Piper aduncum Nutrition 0.000 claims description 2
- 240000003889 Piper guineense Species 0.000 claims description 2
- 235000017804 Piper guineense Nutrition 0.000 claims description 2
- 235000008184 Piper nigrum Nutrition 0.000 claims description 2
- 239000004965 Silica aerogel Substances 0.000 claims description 2
- 235000020224 almond Nutrition 0.000 claims description 2
- 235000011399 aloe vera Nutrition 0.000 claims description 2
- 239000010617 anise oil Substances 0.000 claims description 2
- 239000012298 atmosphere Substances 0.000 claims description 2
- 229960000892 attapulgite Drugs 0.000 claims description 2
- 239000010619 basil oil Substances 0.000 claims description 2
- 229940018006 basil oil Drugs 0.000 claims description 2
- 239000010620 bay oil Substances 0.000 claims description 2
- 239000000440 bentonite Substances 0.000 claims description 2
- 229910000278 bentonite Inorganic materials 0.000 claims description 2
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 claims description 2
- JGQFVRIQXUFPAH-UHFFFAOYSA-N beta-citronellol Natural products OCCC(C)CCCC(C)=C JGQFVRIQXUFPAH-UHFFFAOYSA-N 0.000 claims description 2
- WHGYBXFWUBPSRW-FOUAGVGXSA-N beta-cyclodextrin Chemical compound OC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)CO)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1CO WHGYBXFWUBPSRW-FOUAGVGXSA-N 0.000 claims description 2
- 239000006172 buffering agent Substances 0.000 claims description 2
- 235000005300 cardamomo Nutrition 0.000 claims description 2
- 239000010627 cedar oil Substances 0.000 claims description 2
- 239000001913 cellulose Substances 0.000 claims description 2
- 229920002678 cellulose Polymers 0.000 claims description 2
- 239000010628 chamomile oil Substances 0.000 claims description 2
- 235000019480 chamomile oil Nutrition 0.000 claims description 2
- 239000002738 chelating agent Substances 0.000 claims description 2
- 239000010630 cinnamon oil Substances 0.000 claims description 2
- 235000000983 citronellal Nutrition 0.000 claims description 2
- 229930003633 citronellal Natural products 0.000 claims description 2
- 235000000484 citronellol Nutrition 0.000 claims description 2
- 239000001279 citrus aurantifolia swingle expressed oil Substances 0.000 claims description 2
- 229910052570 clay Inorganic materials 0.000 claims description 2
- 239000010634 clove oil Substances 0.000 claims description 2
- 239000003086 colorant Substances 0.000 claims description 2
- 238000013270 controlled release Methods 0.000 claims description 2
- 239000010636 coriander oil Substances 0.000 claims description 2
- 239000002781 deodorant agent Substances 0.000 claims description 2
- 239000010621 dill oil Substances 0.000 claims description 2
- 239000003974 emollient agent Substances 0.000 claims description 2
- 229940005667 ethyl salicylate Drugs 0.000 claims description 2
- 239000010642 eucalyptus oil Substances 0.000 claims description 2
- 229940044949 eucalyptus oil Drugs 0.000 claims description 2
- 210000003746 feather Anatomy 0.000 claims description 2
- 239000010643 fennel seed oil Substances 0.000 claims description 2
- 239000003349 gelling agent Substances 0.000 claims description 2
- 239000010649 ginger oil Substances 0.000 claims description 2
- 239000010651 grapefruit oil Substances 0.000 claims description 2
- 239000010501 lemon oil Substances 0.000 claims description 2
- 235000001510 limonene Nutrition 0.000 claims description 2
- 229940087305 limonene Drugs 0.000 claims description 2
- 239000001525 mentha piperita l. herb oil Substances 0.000 claims description 2
- 239000001683 mentha spicata herb oil Substances 0.000 claims description 2
- 229940041616 menthol Drugs 0.000 claims description 2
- 229960001047 methyl salicylate Drugs 0.000 claims description 2
- 239000010445 mica Substances 0.000 claims description 2
- 229910052618 mica group Inorganic materials 0.000 claims description 2
- 239000010502 orange oil Substances 0.000 claims description 2
- 229910052625 palygorskite Inorganic materials 0.000 claims description 2
- 239000010663 parsley oil Substances 0.000 claims description 2
- 235000019477 peppermint oil Nutrition 0.000 claims description 2
- 244000144977 poultry Species 0.000 claims description 2
- 239000003755 preservative agent Substances 0.000 claims description 2
- LZFIOSVZIQOVFW-UHFFFAOYSA-N propyl 2-hydroxybenzoate Chemical compound CCCOC(=O)C1=CC=CC=C1O LZFIOSVZIQOVFW-UHFFFAOYSA-N 0.000 claims description 2
- 239000010453 quartz Substances 0.000 claims description 2
- 239000002453 shampoo Substances 0.000 claims description 2
- 235000019721 spearmint oil Nutrition 0.000 claims description 2
- 239000004094 surface-active agent Substances 0.000 claims description 2
- 229920005613 synthetic organic polymer Polymers 0.000 claims description 2
- 239000000454 talc Substances 0.000 claims description 2
- 229910052623 talc Inorganic materials 0.000 claims description 2
- 239000002562 thickening agent Substances 0.000 claims description 2
- 239000010678 thyme oil Substances 0.000 claims description 2
- 239000010681 turmeric oil Substances 0.000 claims description 2
- 239000001993 wax Substances 0.000 claims description 2
- 239000009637 wintergreen oil Substances 0.000 claims description 2
- 241000220317 Rosa Species 0.000 claims 1
- 239000003380 propellant Substances 0.000 claims 1
- 239000005871 repellent Substances 0.000 description 68
- 230000002940 repellent Effects 0.000 description 68
- ZDKZHVNKFOXMND-UHFFFAOYSA-N cis-Nepetalactone Natural products O=C1OC=C(C)C2C1C(C)CC2 ZDKZHVNKFOXMND-UHFFFAOYSA-N 0.000 description 41
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 39
- 239000000126 substance Substances 0.000 description 30
- ZDKZHVNKFOXMND-NBEYISGCSA-N cis-trans-nepetalactone Chemical compound O=C1OC=C(C)[C@@H]2[C@H]1[C@@H](C)CC2 ZDKZHVNKFOXMND-NBEYISGCSA-N 0.000 description 28
- 230000000694 effects Effects 0.000 description 26
- 241000196324 Embryophyta Species 0.000 description 24
- 239000000341 volatile oil Substances 0.000 description 18
- 238000001704 evaporation Methods 0.000 description 16
- 230000008020 evaporation Effects 0.000 description 16
- 239000007788 liquid Substances 0.000 description 16
- 239000000463 material Substances 0.000 description 15
- 239000012528 membrane Substances 0.000 description 14
- 239000000047 product Substances 0.000 description 14
- ZDKZHVNKFOXMND-ZQARSLAVSA-N trans-cis-nepetalactone Chemical compound O=C1OC=C(C)[C@@H]2[C@@H]1[C@@H](C)CC2 ZDKZHVNKFOXMND-ZQARSLAVSA-N 0.000 description 14
- 239000000969 carrier Substances 0.000 description 13
- 238000005984 hydrogenation reaction Methods 0.000 description 13
- 235000010679 Nepeta cataria Nutrition 0.000 description 12
- 240000009215 Nepeta cataria Species 0.000 description 11
- 238000004458 analytical method Methods 0.000 description 11
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 11
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 238000009472 formulation Methods 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- 238000012360 testing method Methods 0.000 description 9
- 241001529733 Nepeta Species 0.000 description 8
- 150000001298 alcohols Chemical class 0.000 description 8
- 238000002474 experimental method Methods 0.000 description 8
- 238000004519 manufacturing process Methods 0.000 description 8
- 239000013641 positive control Substances 0.000 description 8
- 241000607479 Yersinia pestis Species 0.000 description 7
- 235000019645 odor Nutrition 0.000 description 7
- 239000000523 sample Substances 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 241000238876 Acari Species 0.000 description 6
- NIQCNGHVCWTJSM-UHFFFAOYSA-N Dimethyl phthalate Chemical compound COC(=O)C1=CC=CC=C1C(=O)OC NIQCNGHVCWTJSM-UHFFFAOYSA-N 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- 241000257303 Hymenoptera Species 0.000 description 6
- 235000013305 food Nutrition 0.000 description 6
- 230000008569 process Effects 0.000 description 6
- 230000000699 topical effect Effects 0.000 description 6
- RWLALWYNXFYRGW-UHFFFAOYSA-N 2-Ethyl-1,3-hexanediol Chemical compound CCCC(O)C(CC)CO RWLALWYNXFYRGW-UHFFFAOYSA-N 0.000 description 5
- 241000256118 Aedes aegypti Species 0.000 description 5
- 230000003190 augmentative effect Effects 0.000 description 5
- 239000000470 constituent Substances 0.000 description 5
- 230000006378 damage Effects 0.000 description 5
- 229930195733 hydrocarbon Natural products 0.000 description 5
- 239000004615 ingredient Substances 0.000 description 5
- 150000002576 ketones Chemical class 0.000 description 5
- 150000002596 lactones Chemical class 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 229930003658 monoterpene Natural products 0.000 description 5
- 230000001473 noxious effect Effects 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- LSRNBGXEEKNZHN-RBXMUDONSA-N (4r,4ar,7s,7ar)-4,7-dimethyl-4,4a,5,6,7,7a-hexahydro-3h-cyclopenta[c]pyran-1-one Chemical compound [C@@H]1([C@H](COC2=O)C)[C@H]2[C@@H](C)CC1 LSRNBGXEEKNZHN-RBXMUDONSA-N 0.000 description 4
- 241001674044 Blattodea Species 0.000 description 4
- YUXIBTJKHLUKBD-UHFFFAOYSA-N Dibutyl succinate Chemical compound CCCCOC(=O)CCC(=O)OCCCC YUXIBTJKHLUKBD-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 241000257226 Muscidae Species 0.000 description 4
- 238000005481 NMR spectroscopy Methods 0.000 description 4
- 150000001299 aldehydes Chemical class 0.000 description 4
- 125000001931 aliphatic group Chemical group 0.000 description 4
- SESFRYSPDFLNCH-UHFFFAOYSA-N benzyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OCC1=CC=CC=C1 SESFRYSPDFLNCH-UHFFFAOYSA-N 0.000 description 4
- 239000002775 capsule Substances 0.000 description 4
- DOIRQSBPFJWKBE-UHFFFAOYSA-N dibutyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 4
- IITCWRFYJWUUPC-UHFFFAOYSA-N dipropyl pyridine-2,5-dicarboxylate Chemical compound CCCOC(=O)C1=CC=C(C(=O)OCCC)N=C1 IITCWRFYJWUUPC-UHFFFAOYSA-N 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 229940060367 inert ingredients Drugs 0.000 description 4
- 150000002500 ions Chemical class 0.000 description 4
- 150000002894 organic compounds Chemical class 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- 238000001228 spectrum Methods 0.000 description 4
- 238000001256 steam distillation Methods 0.000 description 4
- 235000007586 terpenes Nutrition 0.000 description 4
- HMCYXRFNNOPPPR-JLIMGVALSA-N (1s,2s,5r)-2-methyl-5-[(2s)-1-oxopropan-2-yl]cyclopentane-1-carbaldehyde Chemical compound O=C[C@@H](C)[C@H]1CC[C@H](C)[C@@H]1C=O HMCYXRFNNOPPPR-JLIMGVALSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- 241000282412 Homo Species 0.000 description 3
- MMOXZBCLCQITDF-UHFFFAOYSA-N N,N-diethyl-m-toluamide Chemical compound CCN(CC)C(=O)C1=CC=CC(C)=C1 MMOXZBCLCQITDF-UHFFFAOYSA-N 0.000 description 3
- 241000533333 Nepeta racemosa Species 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- FAMPSKZZVDUYOS-UHFFFAOYSA-N alpha-Caryophyllene Natural products CC1=CCC(C)(C)C=CCC(C)=CCC1 FAMPSKZZVDUYOS-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000001460 carbon-13 nuclear magnetic resonance spectrum Methods 0.000 description 3
- 230000008859 change Effects 0.000 description 3
- ZDKZHVNKFOXMND-XVYDVKMFSA-N cis-cis-nepetalactone Chemical compound O=C1OC=C(C)[C@H]2[C@@H]1[C@@H](C)CC2 ZDKZHVNKFOXMND-XVYDVKMFSA-N 0.000 description 3
- 230000008878 coupling Effects 0.000 description 3
- 238000010168 coupling process Methods 0.000 description 3
- 238000005859 coupling reaction Methods 0.000 description 3
- HMCYXRFNNOPPPR-UHFFFAOYSA-N delta-Iridodial Natural products O=CC(C)C1CCC(C)C1C=O HMCYXRFNNOPPPR-UHFFFAOYSA-N 0.000 description 3
- FBSAITBEAPNWJG-UHFFFAOYSA-N dimethyl phthalate Natural products CC(=O)OC1=CC=CC=C1OC(C)=O FBSAITBEAPNWJG-UHFFFAOYSA-N 0.000 description 3
- 229960001826 dimethylphthalate Drugs 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 238000009826 distribution Methods 0.000 description 3
- 239000000428 dust Substances 0.000 description 3
- 238000013401 experimental design Methods 0.000 description 3
- 239000000284 extract Substances 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- 239000004744 fabric Substances 0.000 description 3
- 239000010408 film Substances 0.000 description 3
- 238000004508 fractional distillation Methods 0.000 description 3
- 150000002430 hydrocarbons Chemical class 0.000 description 3
- 239000002917 insecticide Substances 0.000 description 3
- LYEFRAMOOLOUKA-UHFFFAOYSA-N isoepiiridomyrmecin Natural products C1OC(=O)C(C)C2C1C(C)CC2 LYEFRAMOOLOUKA-UHFFFAOYSA-N 0.000 description 3
- 238000001819 mass spectrum Methods 0.000 description 3
- OJGPEAXUHQRLNC-UHFFFAOYSA-N nepetalactol Natural products OC1OC=C(C)C2C1C(C)CC2 OJGPEAXUHQRLNC-UHFFFAOYSA-N 0.000 description 3
- 230000035515 penetration Effects 0.000 description 3
- 239000002304 perfume Substances 0.000 description 3
- 235000019271 petrolatum Nutrition 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- 230000028327 secretion Effects 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000000638 solvent extraction Methods 0.000 description 3
- 231100000331 toxic Toxicity 0.000 description 3
- 230000002588 toxic effect Effects 0.000 description 3
- LYEFRAMOOLOUKA-XGEHTFHBSA-N (4s,4ar,7r,7as)-4,7-dimethyl-4,4a,5,6,7,7a-hexahydro-1h-cyclopenta[c]pyran-3-one Chemical compound [C@H]1([C@@H](C(=O)OC2)C)[C@@H]2[C@H](C)CC1 LYEFRAMOOLOUKA-XGEHTFHBSA-N 0.000 description 2
- LSRNBGXEEKNZHN-JQCXWYLXSA-N (4s,4ar,7s,7ar)-4,7-dimethyl-4,4a,5,6,7,7a-hexahydro-3h-cyclopenta[c]pyran-1-one Chemical compound [C@@H]1([C@@H](COC2=O)C)[C@H]2[C@@H](C)CC1 LSRNBGXEEKNZHN-JQCXWYLXSA-N 0.000 description 2
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 2
- DSKYSDCYIODJPC-UHFFFAOYSA-N 2-butyl-2-ethylpropane-1,3-diol Chemical compound CCCCC(CC)(CO)CO DSKYSDCYIODJPC-UHFFFAOYSA-N 0.000 description 2
- AAIBYZBZXNWTPP-UHFFFAOYSA-N 2-phenylcyclohexan-1-ol Chemical compound OC1CCCCC1C1=CC=CC=C1 AAIBYZBZXNWTPP-UHFFFAOYSA-N 0.000 description 2
- XNYGOEGATLFFOX-UHFFFAOYSA-N 4,5a,6,9,9a,9b-hexahydro-1h-dibenzofuran-4a-carbaldehyde Chemical compound C12CC=CCC2OC2(C=O)C1CC=CC2 XNYGOEGATLFFOX-UHFFFAOYSA-N 0.000 description 2
- 241000256111 Aedes <genus> Species 0.000 description 2
- 241000283690 Bos taurus Species 0.000 description 2
- 241001388466 Bruchus rufimanus Species 0.000 description 2
- 241000254171 Curculionidae Species 0.000 description 2
- XTJFFFGAUHQWII-UHFFFAOYSA-N Dibutyl adipate Chemical compound CCCCOC(=O)CCCCC(=O)OCCCC XTJFFFGAUHQWII-UHFFFAOYSA-N 0.000 description 2
- 241000520382 Iridomyrmex Species 0.000 description 2
- 241000256602 Isoptera Species 0.000 description 2
- 241000207923 Lamiaceae Species 0.000 description 2
- 244000165082 Lavanda vera Species 0.000 description 2
- 241001124553 Lepismatidae Species 0.000 description 2
- 244000062730 Melissa officinalis Species 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- 241000131095 Oniscidea Species 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- 244000124853 Perilla frutescens Species 0.000 description 2
- 239000004264 Petrolatum Substances 0.000 description 2
- 241000256103 Simuliidae Species 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- 241000256856 Vespidae Species 0.000 description 2
- 239000011149 active material Substances 0.000 description 2
- 239000003242 anti bacterial agent Substances 0.000 description 2
- WURBFLDFSFBTLW-UHFFFAOYSA-N benzil Chemical compound C=1C=CC=CC=1C(=O)C(=O)C1=CC=CC=C1 WURBFLDFSFBTLW-UHFFFAOYSA-N 0.000 description 2
- 229960002903 benzyl benzoate Drugs 0.000 description 2
- 125000002619 bicyclic group Chemical group 0.000 description 2
- 239000008280 blood Substances 0.000 description 2
- 210000004369 blood Anatomy 0.000 description 2
- QLHULAHOXSSASE-UHFFFAOYSA-N butan-2-yl 2-(2-hydroxyethyl)piperidine-1-carboxylate Chemical compound CCC(C)OC(=O)N1CCCCC1CCO QLHULAHOXSSASE-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 2
- 230000002950 deficient Effects 0.000 description 2
- 229940100539 dibutyl adipate Drugs 0.000 description 2
- VGQLNJWOULYVFV-SPJNRGJMSA-N dimethylcarbate Chemical compound C1[C@H]2C=C[C@@H]1[C@H](C(=O)OC)[C@@H]2C(=O)OC VGQLNJWOULYVFV-SPJNRGJMSA-N 0.000 description 2
- 229960004118 dimethylcarbate Drugs 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 239000003995 emulsifying agent Substances 0.000 description 2
- 230000002708 enhancing effect Effects 0.000 description 2
- 230000001747 exhibiting effect Effects 0.000 description 2
- 239000012467 final product Substances 0.000 description 2
- 239000000796 flavoring agent Substances 0.000 description 2
- 235000019634 flavors Nutrition 0.000 description 2
- 235000013312 flour Nutrition 0.000 description 2
- 238000005755 formation reaction Methods 0.000 description 2
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 238000003306 harvesting Methods 0.000 description 2
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- 230000001965 increasing effect Effects 0.000 description 2
- 229910003480 inorganic solid Inorganic materials 0.000 description 2
- 230000000749 insecticidal effect Effects 0.000 description 2
- 239000002480 mineral oil Substances 0.000 description 2
- 235000010446 mineral oil Nutrition 0.000 description 2
- ZWDZJRRQSXLOQR-UHFFFAOYSA-N n-butyl-n-phenylacetamide Chemical compound CCCCN(C(C)=O)C1=CC=CC=C1 ZWDZJRRQSXLOQR-UHFFFAOYSA-N 0.000 description 2
- 229930014626 natural product Natural products 0.000 description 2
- VKCYHJWLYTUGCC-UHFFFAOYSA-N nonan-2-one Chemical compound CCCCCCCC(C)=O VKCYHJWLYTUGCC-UHFFFAOYSA-N 0.000 description 2
- BBNYLDSWVXSNOQ-UHFFFAOYSA-N oxolane-2-carbaldehyde Chemical compound O=CC1CCCO1 BBNYLDSWVXSNOQ-UHFFFAOYSA-N 0.000 description 2
- LMXFTMYMHGYJEI-UHFFFAOYSA-N p-menthane-3,8-diol Chemical compound CC1CCC(C(C)(C)O)C(O)C1 LMXFTMYMHGYJEI-UHFFFAOYSA-N 0.000 description 2
- 229930006948 p-menthane-3,8-diol Natural products 0.000 description 2
- 239000000123 paper Substances 0.000 description 2
- 239000012188 paraffin wax Substances 0.000 description 2
- 239000000575 pesticide Substances 0.000 description 2
- 229940066842 petrolatum Drugs 0.000 description 2
- 239000003209 petroleum derivative Substances 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 239000002574 poison Substances 0.000 description 2
- 231100000614 poison Toxicity 0.000 description 2
- 229920001296 polysiloxane Polymers 0.000 description 2
- 239000013014 purified material Substances 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 239000011343 solid material Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 241000894007 species Species 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 230000001502 supplementing effect Effects 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 239000003784 tall oil Substances 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- GRWFGVWFFZKLTI-UHFFFAOYSA-N α-pinene Chemical compound CC1=CCC2C(C)(C)C1C2 GRWFGVWFFZKLTI-UHFFFAOYSA-N 0.000 description 2
- NPNUFJAVOOONJE-ZIAGYGMSSA-N β-(E)-Caryophyllene Chemical compound C1CC(C)=CCCC(=C)[C@H]2CC(C)(C)[C@@H]21 NPNUFJAVOOONJE-ZIAGYGMSSA-N 0.000 description 2
- SNICXCGAKADSCV-JTQLQIEISA-N (-)-Nicotine Chemical compound CN1CCC[C@H]1C1=CC=CN=C1 SNICXCGAKADSCV-JTQLQIEISA-N 0.000 description 1
- LSRNBGXEEKNZHN-MAUMQABQSA-N (4r,4ar,7s,7as)-4,7-dimethyl-4,4a,5,6,7,7a-hexahydro-3h-cyclopenta[c]pyran-1-one Chemical compound [C@@H]1([C@H](COC2=O)C)[C@@H]2[C@@H](C)CC1 LSRNBGXEEKNZHN-MAUMQABQSA-N 0.000 description 1
- LSRNBGXEEKNZHN-KDXUFGMBSA-N (4s,4ar,7s,7as)-4,7-dimethyl-4,4a,5,6,7,7a-hexahydro-3h-cyclopenta[c]pyran-1-one Chemical compound [C@@H]1([C@@H](COC2=O)C)[C@@H]2[C@@H](C)CC1 LSRNBGXEEKNZHN-KDXUFGMBSA-N 0.000 description 1
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
- LQIAZOCLNBBZQK-UHFFFAOYSA-N 1-(1,2-Diphosphanylethyl)pyrrolidin-2-one Chemical compound PCC(P)N1CCCC1=O LQIAZOCLNBBZQK-UHFFFAOYSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- GRWFGVWFFZKLTI-IUCAKERBSA-N 1S,5S-(-)-alpha-Pinene Natural products CC1=CC[C@@H]2C(C)(C)[C@H]1C2 GRWFGVWFFZKLTI-IUCAKERBSA-N 0.000 description 1
- 238000005084 2D-nuclear magnetic resonance Methods 0.000 description 1
- NVEQFIOZRFFVFW-UHFFFAOYSA-N 9-epi-beta-caryophyllene oxide Natural products C=C1CCC2OC2(C)CCC2C(C)(C)CC21 NVEQFIOZRFFVFW-UHFFFAOYSA-N 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- 241000238657 Blattella germanica Species 0.000 description 1
- 241000282472 Canis lupus familiaris Species 0.000 description 1
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
- 206010053567 Coagulopathies Diseases 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 244000166675 Cymbopogon nardus Species 0.000 description 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
- HEBKCHPVOIAQTA-QWWZWVQMSA-N D-arabinitol Chemical compound OC[C@@H](O)C(O)[C@H](O)CO HEBKCHPVOIAQTA-QWWZWVQMSA-N 0.000 description 1
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
- YVGGHNCTFXOJCH-UHFFFAOYSA-N DDT Chemical compound C1=CC(Cl)=CC=C1C(C(Cl)(Cl)Cl)C1=CC=C(Cl)C=C1 YVGGHNCTFXOJCH-UHFFFAOYSA-N 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- 239000004386 Erythritol Substances 0.000 description 1
- UNXHWFMMPAWVPI-UHFFFAOYSA-N Erythritol Natural products OCC(O)C(O)CO UNXHWFMMPAWVPI-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 208000006877 Insect Bites and Stings Diseases 0.000 description 1
- LYEFRAMOOLOUKA-RBXMUDONSA-N Iridomyrmecin Chemical compound [C@@H]1([C@@H](C(=O)OC2)C)[C@H]2[C@@H](C)CC1 LYEFRAMOOLOUKA-RBXMUDONSA-N 0.000 description 1
- 244000032014 Java citronella Species 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- 235000002997 Lavandula Nutrition 0.000 description 1
- 235000010663 Lavandula angustifolia Nutrition 0.000 description 1
- 235000010654 Melissa officinalis Nutrition 0.000 description 1
- 239000005662 Paraffin oil Substances 0.000 description 1
- 235000004347 Perilla Nutrition 0.000 description 1
- 235000004348 Perilla frutescens Nutrition 0.000 description 1
- 240000002505 Pogostemon cablin Species 0.000 description 1
- 235000011751 Pogostemon cablin Nutrition 0.000 description 1
- 208000005374 Poisoning Diseases 0.000 description 1
- 229920001131 Pulp (paper) Polymers 0.000 description 1
- 241000382353 Pupa Species 0.000 description 1
- 230000002292 Radical scavenging effect Effects 0.000 description 1
- 206010040880 Skin irritation Diseases 0.000 description 1
- 241001157802 Staphylinidae Species 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 239000004433 Thermoplastic polyurethane Substances 0.000 description 1
- 241001511571 Trichomyrmex destructor 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
- 210000001015 abdomen Anatomy 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- TTWYZDPBDWHJOR-IDIVVRGQSA-L adenosine triphosphate disodium Chemical compound [Na+].[Na+].C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](COP(O)(=O)OP(O)(=O)OP([O-])([O-])=O)[C@@H](O)[C@H]1O TTWYZDPBDWHJOR-IDIVVRGQSA-L 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 239000002386 air freshener Substances 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 230000000172 allergic effect Effects 0.000 description 1
- 229940061720 alpha hydroxy acid Drugs 0.000 description 1
- 150000001280 alpha hydroxy acids Chemical class 0.000 description 1
- MVNCAPSFBDBCGF-UHFFFAOYSA-N alpha-pinene Natural products CC1=CCC23C1CC2C3(C)C MVNCAPSFBDBCGF-UHFFFAOYSA-N 0.000 description 1
- WUOACPNHFRMFPN-UHFFFAOYSA-N alpha-terpineol Chemical compound CC1=CCC(C(C)(C)O)CC1 WUOACPNHFRMFPN-UHFFFAOYSA-N 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 210000003503 anal sac Anatomy 0.000 description 1
- 229940121363 anti-inflammatory agent Drugs 0.000 description 1
- 239000002260 anti-inflammatory agent Substances 0.000 description 1
- 230000002421 anti-septic effect Effects 0.000 description 1
- 229940088710 antibiotic agent Drugs 0.000 description 1
- 229940125715 antihistaminic agent Drugs 0.000 description 1
- 239000000739 antihistaminic agent Substances 0.000 description 1
- 229940064004 antiseptic throat preparations Drugs 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 239000010692 aromatic oil Substances 0.000 description 1
- 229910052785 arsenic Inorganic materials 0.000 description 1
- RQNWIZPPADIBDY-UHFFFAOYSA-N arsenic atom Chemical compound [As] RQNWIZPPADIBDY-UHFFFAOYSA-N 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 208000010668 atopic eczema Diseases 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- NPNUFJAVOOONJE-UHFFFAOYSA-N beta-cariophyllene Natural products C1CC(C)=CCCC(=C)C2CC(C)(C)C21 NPNUFJAVOOONJE-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 235000011089 carbon dioxide Nutrition 0.000 description 1
- 229940117948 caryophyllene Drugs 0.000 description 1
- NPNUFJAVOOONJE-UONOGXRCSA-N caryophyllene Natural products C1CC(C)=CCCC(=C)[C@@H]2CC(C)(C)[C@@H]21 NPNUFJAVOOONJE-UONOGXRCSA-N 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 229960000541 cetyl alcohol Drugs 0.000 description 1
- 210000000038 chest Anatomy 0.000 description 1
- BIWJNBZANLAXMG-YQELWRJZSA-N chloordaan Chemical compound ClC1=C(Cl)[C@@]2(Cl)C3CC(Cl)C(Cl)C3[C@]1(Cl)C2(Cl)Cl BIWJNBZANLAXMG-YQELWRJZSA-N 0.000 description 1
- 230000035602 clotting Effects 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 229940120693 copper naphthenate Drugs 0.000 description 1
- SEVNKWFHTNVOLD-UHFFFAOYSA-L copper;3-(4-ethylcyclohexyl)propanoate;3-(3-ethylcyclopentyl)propanoate Chemical compound [Cu+2].CCC1CCC(CCC([O-])=O)C1.CCC1CCC(CCC([O-])=O)CC1 SEVNKWFHTNVOLD-UHFFFAOYSA-L 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 239000002178 crystalline material Substances 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- SQIFACVGCPWBQZ-UHFFFAOYSA-N delta-terpineol Natural products CC(C)(O)C1CCC(=C)CC1 SQIFACVGCPWBQZ-UHFFFAOYSA-N 0.000 description 1
- DFBKLUNHFCTMDC-PICURKEMSA-N dieldrin Chemical compound C([C@H]1[C@H]2[C@@]3(Cl)C(Cl)=C([C@]([C@H]22)(Cl)C3(Cl)Cl)Cl)[C@H]2[C@@H]2[C@H]1O2 DFBKLUNHFCTMDC-PICURKEMSA-N 0.000 description 1
- NGPMUTDCEIKKFM-UHFFFAOYSA-N dieldrin Natural products CC1=C(Cl)C2(Cl)C3C4CC(C5OC45)C3C1(Cl)C2(Cl)Cl NGPMUTDCEIKKFM-UHFFFAOYSA-N 0.000 description 1
- 229950006824 dieldrin Drugs 0.000 description 1
- 230000029087 digestion Effects 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000005538 encapsulation Methods 0.000 description 1
- DFBKLUNHFCTMDC-GKRDHZSOSA-N endrin Chemical compound C([C@@H]1[C@H]2[C@@]3(Cl)C(Cl)=C([C@]([C@H]22)(Cl)C3(Cl)Cl)Cl)[C@@H]2[C@H]2[C@@H]1O2 DFBKLUNHFCTMDC-GKRDHZSOSA-N 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000003623 enhancer Substances 0.000 description 1
- UNXHWFMMPAWVPI-ZXZARUISSA-N erythritol Chemical compound OC[C@H](O)[C@H](O)CO UNXHWFMMPAWVPI-ZXZARUISSA-N 0.000 description 1
- 229940009714 erythritol Drugs 0.000 description 1
- 235000019414 erythritol Nutrition 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- YSPVHAUJXLGZHP-UHFFFAOYSA-N ethyl piperidine-1-carboxylate Chemical compound CCOC(=O)N1CCCCC1 YSPVHAUJXLGZHP-UHFFFAOYSA-N 0.000 description 1
- 239000003925 fat Substances 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000000834 fixative Substances 0.000 description 1
- 230000037406 food intake Effects 0.000 description 1
- 239000003517 fume Substances 0.000 description 1
- 239000002316 fumigant Substances 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- JLYXXMFPNIAWKQ-GNIYUCBRSA-N gamma-hexachlorocyclohexane Chemical compound Cl[C@H]1[C@H](Cl)[C@@H](Cl)[C@@H](Cl)[C@H](Cl)[C@H]1Cl JLYXXMFPNIAWKQ-GNIYUCBRSA-N 0.000 description 1
- JLYXXMFPNIAWKQ-UHFFFAOYSA-N gamma-hexachlorocyclohexane Natural products ClC1C(Cl)C(Cl)C(Cl)C(Cl)C1Cl JLYXXMFPNIAWKQ-UHFFFAOYSA-N 0.000 description 1
- BXWQUXUDAGDUOS-UHFFFAOYSA-N gamma-humulene Natural products CC1=CCCC(C)(C)C=CC(=C)CCC1 BXWQUXUDAGDUOS-UHFFFAOYSA-N 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 230000001339 gustatory effect Effects 0.000 description 1
- 210000003128 head Anatomy 0.000 description 1
- 229920001903 high density polyethylene Polymers 0.000 description 1
- 239000004700 high-density polyethylene Substances 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- QBNFBHXQESNSNP-UHFFFAOYSA-N humulene Natural products CC1=CC=CC(C)(C)CC=C(/C)CCC1 QBNFBHXQESNSNP-UHFFFAOYSA-N 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 239000000976 ink Substances 0.000 description 1
- 150000002484 inorganic compounds Chemical class 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 229940033518 insecticides and repellents Drugs 0.000 description 1
- 239000011872 intimate mixture Substances 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 238000002955 isolation Methods 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
- 239000003350 kerosene Substances 0.000 description 1
- 239000004922 lacquer Substances 0.000 description 1
- 150000003951 lactams Chemical class 0.000 description 1
- 239000001102 lavandula vera Substances 0.000 description 1
- 235000018219 lavender Nutrition 0.000 description 1
- 229960002809 lindane Drugs 0.000 description 1
- 229920001684 low density polyethylene Polymers 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 239000004702 low-density polyethylene Substances 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- HEBKCHPVOIAQTA-UHFFFAOYSA-N meso ribitol Natural products OCC(O)C(O)C(O)CO HEBKCHPVOIAQTA-UHFFFAOYSA-N 0.000 description 1
- 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 239000003094 microcapsule Substances 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000003595 mist Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- 150000002773 monoterpene derivatives Chemical class 0.000 description 1
- 235000002577 monoterpenes Nutrition 0.000 description 1
- 229960002715 nicotine Drugs 0.000 description 1
- SNICXCGAKADSCV-UHFFFAOYSA-N nicotine Natural products CN1CCCC1C1=CC=CN=C1 SNICXCGAKADSCV-UHFFFAOYSA-N 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- ZCYXXKJEDCHMGH-UHFFFAOYSA-N nonane Chemical compound CCCC[CH]CCCC ZCYXXKJEDCHMGH-UHFFFAOYSA-N 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 231100000956 nontoxicity Toxicity 0.000 description 1
- BKIMMITUMNQMOS-UHFFFAOYSA-N normal nonane Natural products CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 1
- LCCNCVORNKJIRZ-UHFFFAOYSA-N parathion Chemical compound CCOP(=S)(OCC)OC1=CC=C([N+]([O-])=O)C=C1 LCCNCVORNKJIRZ-UHFFFAOYSA-N 0.000 description 1
- 230000001717 pathogenic effect Effects 0.000 description 1
- 230000002688 persistence Effects 0.000 description 1
- 239000000419 plant extract Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 231100000572 poisoning Toxicity 0.000 description 1
- 230000000607 poisoning effect Effects 0.000 description 1
- 229920001610 polycaprolactone Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000004262 preparative liquid chromatography Methods 0.000 description 1
- 238000012746 preparative thin layer chromatography Methods 0.000 description 1
- 230000002035 prolonged effect Effects 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
- 239000002516 radical scavenger Substances 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 239000010666 rose oil Substances 0.000 description 1
- 235000019719 rose oil Nutrition 0.000 description 1
- 229940080817 rotenone Drugs 0.000 description 1
- JUVIOZPCNVVQFO-UHFFFAOYSA-N rotenone Natural products O1C2=C3CC(C(C)=C)OC3=CC=C2C(=O)C2C1COC1=C2C=C(OC)C(OC)=C1 JUVIOZPCNVVQFO-UHFFFAOYSA-N 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 230000036556 skin irritation Effects 0.000 description 1
- 231100000475 skin irritation Toxicity 0.000 description 1
- 239000001509 sodium citrate Substances 0.000 description 1
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 230000007480 spreading Effects 0.000 description 1
- 238000003892 spreading Methods 0.000 description 1
- 230000004936 stimulating effect Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 239000000516 sunscreening agent Substances 0.000 description 1
- 238000000194 supercritical-fluid extraction Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000035900 sweating Effects 0.000 description 1
- 239000012438 synthetic essential oil Substances 0.000 description 1
- 229940116411 terpineol Drugs 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 229920002803 thermoplastic polyurethane Polymers 0.000 description 1
- 239000012049 topical pharmaceutical composition Substances 0.000 description 1
- 231100000027 toxicology Toxicity 0.000 description 1
- 239000013598 vector Substances 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 235000013343 vitamin Nutrition 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
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
- A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
- A01N43/14—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom six-membered rings
- A01N43/16—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom six-membered rings with oxygen as the ring hetero atom
-
- 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
- A01N65/00—Biocides, pest repellants or attractants, or plant growth regulators containing material from algae, lichens, bryophyta, multi-cellular fungi or plants, or extracts thereof
- A01N65/08—Magnoliopsida [dicotyledons]
- A01N65/22—Lamiaceae or Labiatae [Mint family], e.g. thyme, rosemary, skullcap, selfheal, lavender, perilla, pennyroyal, peppermint or spearmint
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/02—Drugs for dermatological disorders for treating wounds, ulcers, burns, scars, keloids, or the like
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T442/00—Fabric [woven, knitted, or nonwoven textile or cloth, etc.]
- Y10T442/20—Coated or impregnated woven, knit, or nonwoven fabric which is not [a] associated with another preformed layer or fiber layer or, [b] with respect to woven and knit, characterized, respectively, by a particular or differential weave or knit, wherein the coating or impregnation is neither a foamed material nor a free metal or alloy layer
- Y10T442/2525—Coating or impregnation functions biologically [e.g., insect repellent, antiseptic, insecticide, bactericide, etc.]
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Environmental Sciences (AREA)
- Zoology (AREA)
- Wood Science & Technology (AREA)
- Dentistry (AREA)
- Plant Pathology (AREA)
- Agronomy & Crop Science (AREA)
- Natural Medicines & Medicinal Plants (AREA)
- Pest Control & Pesticides (AREA)
- Biotechnology (AREA)
- Microbiology (AREA)
- Mycology (AREA)
- Organic Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Animal Behavior & Ethology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Medicinal Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Chemical & Material Sciences (AREA)
- Dermatology (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Cosmetics (AREA)
- Fats And Perfumes (AREA)
- Medicinal Preparation (AREA)
- Paints Or Removers (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US36614702P | 2002-03-20 | 2002-03-20 | |
| US60/366,147 | 2002-03-20 | ||
| PCT/US2003/008516 WO2003079786A1 (en) | 2002-03-20 | 2003-03-20 | Dihydronepetalactone as insect repellent |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU2003214243A1 AU2003214243A1 (en) | 2003-10-08 |
| AU2003214243B2 true AU2003214243B2 (en) | 2008-02-14 |
Family
ID=28454757
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2003214243A Ceased AU2003214243B2 (en) | 2002-03-20 | 2003-03-20 | Dihydronepetalactone as insect repellent |
Country Status (14)
| Country | Link |
|---|---|
| US (4) | US20030235601A1 (https=) |
| EP (1) | EP1484967B1 (https=) |
| JP (1) | JP2005520837A (https=) |
| KR (1) | KR20040097182A (https=) |
| CN (1) | CN100521939C (https=) |
| AU (1) | AU2003214243B2 (https=) |
| BR (2) | BRPI0308639B1 (https=) |
| CA (1) | CA2479123C (https=) |
| ES (1) | ES2397512T3 (https=) |
| HK (1) | HK1079659A1 (https=) |
| MX (1) | MXPA04008994A (https=) |
| RU (1) | RU2004130863A (https=) |
| WO (1) | WO2003079786A1 (https=) |
| ZA (1) | ZA200406233B (https=) |
Families Citing this family (75)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN100396674C (zh) * | 2002-01-23 | 2008-06-25 | 纳幕尔杜邦公司 | 芳香化合物 |
| US7547793B2 (en) * | 2003-03-19 | 2009-06-16 | E.I. Du Pont De Nemours And Company | Method for making insect repellent composition |
| US7943160B2 (en) * | 2002-05-09 | 2011-05-17 | Scimetrics Limited Corp. | Pest control methods |
| US20040197362A1 (en) * | 2003-04-04 | 2004-10-07 | Wagner Cassandra Marie | Bugnip |
| EP1667698B1 (en) * | 2003-05-22 | 2009-03-18 | Bioniche Life Sciences Inc. | Insect repellent |
| GB0320351D0 (en) * | 2003-08-29 | 2003-10-01 | Yates Donald H | A preparation against flying insects that bite |
| US20050058681A1 (en) * | 2003-09-12 | 2005-03-17 | Johnson Louis B. | Odorless insect repellant and method of use |
| JP2007521240A (ja) * | 2003-09-18 | 2007-08-02 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー | ジヒドロネペタラクトンを含んでなる昆虫忌避組成物 |
| CN1953971A (zh) * | 2003-11-26 | 2007-04-25 | 纳幕尔杜邦公司 | 二氢假荆芥内酯衍生物及其制备方法 |
| US20050137252A1 (en) * | 2003-12-22 | 2005-06-23 | Scialdone Mark A. | Production of dihydronepetalactone |
| US7341736B2 (en) * | 2004-01-30 | 2008-03-11 | S.C. Johnson & Son, Inc. | Aerosol spray resistant to discoloration |
| US7503675B2 (en) * | 2004-03-03 | 2009-03-17 | S.C. Johnson & Son, Inc. | Combination light device with insect control ingredient emission |
| US20050202106A1 (en) * | 2004-03-09 | 2005-09-15 | Friedrikis Russell R. | Mosquito repellent compositions |
| CA2567246A1 (en) * | 2004-05-20 | 2005-12-01 | Nelson Mandela Metropolitan University | Insect repellent compositions |
| CA2584354C (en) * | 2004-11-03 | 2015-02-24 | E.I. Du Pont De Nemours And Company | Insect repellent compositions comprising dihydronepetalactone, an alcohol and an ester |
| EP1655344A1 (en) * | 2004-11-05 | 2006-05-10 | The Procter & Gamble Company | Polymeric compositions for sustained release of volatile materials |
| US7375239B2 (en) | 2004-12-08 | 2008-05-20 | The United States Of America As Represented By The Secretary Of Agriculture | Methods of separating ZE-nepetalactone and EZ-nepetalactone from catnip oil |
| US20060148842A1 (en) * | 2004-12-29 | 2006-07-06 | Scialdone Mark A | Nepetalactams and N-substituted derivatives thereof |
| JP2008526769A (ja) * | 2004-12-29 | 2008-07-24 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー | ジヒドロネペタラクタムおよびそのｎ−置換誘導体 |
| US20060201391A1 (en) * | 2005-03-09 | 2006-09-14 | Scialdone Mark A | Compositions having sustained-release insect repellency |
| JP2006335724A (ja) * | 2005-06-03 | 2006-12-14 | S T Chem Co Ltd | 防虫剤及び防虫方法 |
| US7741266B2 (en) * | 2005-06-20 | 2010-06-22 | Rotuba Extruders, Inc. | Process for preparing scented cellulosics and products prepared thereby |
| US20070092544A1 (en) * | 2005-08-23 | 2007-04-26 | Mills Matthew A | Natural insect repellant |
| US8236334B2 (en) * | 2005-09-06 | 2012-08-07 | Bass James S | Composition and method for killing insects |
| BRPI0617592A2 (pt) | 2005-09-30 | 2011-08-02 | Du Pont | composto, composição, método para repelir um inseto ou artrópode e processo para a preparação de um composto |
| US20130165506A1 (en) * | 2005-09-30 | 2013-06-27 | E I Du Pont De Nemours And Company | Puleganic acid insect repellent |
| CN101316510A (zh) * | 2005-09-30 | 2008-12-03 | 纳幕尔杜邦公司 | 蒲勒酸昆虫驱避剂 |
| US7261742B2 (en) | 2005-10-13 | 2007-08-28 | S.C. Johnson & Son, Inc. | Method of deodorizing a textile |
| US7407922B2 (en) | 2005-10-13 | 2008-08-05 | S.C. Johnson & Son, Inc. | Deodorizing compositions |
| KR100756397B1 (ko) * | 2006-04-24 | 2007-09-10 | 충북대학교 산학협력단 | 모기 기피용 조성물 |
| CA2648270C (en) * | 2006-05-10 | 2014-07-08 | E.I. Du Pont De Nemours And Company | Formulated tick and insect repellent compositions comprising dihydronepetalactone |
| US7776912B2 (en) * | 2006-06-30 | 2010-08-17 | E.I. Du Pont De Nemours And Company | Acetals of nepetalic acid and method of preparation |
| SI2114911T1 (sl) * | 2006-12-21 | 2015-12-31 | E.I. Du Pont De Nemours And Company | Produkcija dihidronepetalaktona s hidrogeniranjem nepetalaktona |
| BRPI0719453A2 (pt) * | 2006-12-21 | 2014-03-18 | Du Pont | Processo de preparação de óleo de erva dos gatos hidrogenado, processo de preparação de produtos formulados com um óleo de erva dos gatos hidrogenado e óleo de erva dos gatos hidrogenado |
| WO2008079253A1 (en) | 2006-12-21 | 2008-07-03 | E. I. Du Pont De Nemours And Company | Hydrogenation of catmint oil |
| SI2121885T1 (sl) | 2006-12-21 | 2017-10-30 | E.I. Du Pont De Nemours And Company | Parna destilacija mačje mete |
| US9521844B2 (en) | 2006-12-21 | 2016-12-20 | E I Du Pont De Nemours And Company | Solvent addition and removal in the hydrogenation of catmint oil |
| MX2009010488A (es) | 2007-03-28 | 2010-03-15 | Contech Entpr Inc | Compuestos de sulfuro de alilo y composiciones y metodos que utilizan tales compuestos para repeler artropodos hematofagos. |
| US20080274072A1 (en) * | 2007-05-04 | 2008-11-06 | John Manolas | Insect repellants and insecticides |
| KR100754416B1 (ko) * | 2007-05-17 | 2007-08-31 | (주)바이오앤에이치엔티 | 모기 기피제 조성물 |
| DE102007026051A1 (de) * | 2007-05-31 | 2008-12-04 | Beiersdorf Ag | Insektenschutzmittel mit reduzierter Klebrigkeit |
| DE102007026053A1 (de) * | 2007-05-31 | 2008-12-04 | Beiersdorf Ag | Insektenschutzmittel mit guter Hautverträglichkeit |
| US20100140368A1 (en) * | 2007-06-25 | 2010-06-10 | The Dial Corporation | Non-hazardous foaming ant spray based on natural oils, carboxylate salts and optional synergists |
| US8741874B2 (en) * | 2007-11-07 | 2014-06-03 | Bayer Cropscience Lp | Insecticidal compositions with disinfectant |
| CA2705367C (en) | 2007-11-26 | 2016-05-31 | E.I. Du Pont De Nemours And Company | Method for converting trans-cis nepetalactone to cis-trans nepetalactone using molecular sieves |
| US20090246241A1 (en) * | 2008-03-26 | 2009-10-01 | Kathleen Pitt | Animal pest repellant device |
| US8691340B2 (en) | 2008-12-31 | 2014-04-08 | Apinee, Inc. | Preservation of wood, compositions and methods thereof |
| JP5805099B2 (ja) | 2009-11-11 | 2015-11-04 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニーＥ．Ｉ．Ｄｕ Ｐｏｎｔ Ｄｅ Ｎｅｍｏｕｒｓ Ａｎｄ Ｃｏｍｐａｎｙ | イヌハッカ油の回収を向上させる方法 |
| KR101167069B1 (ko) * | 2010-01-14 | 2012-07-27 | 전진바이오팜 주식회사 | 천연물질로 이루어진 야생동물 기피제 조성물 |
| US9878464B1 (en) | 2011-06-30 | 2018-01-30 | Apinee, Inc. | Preservation of cellulosic materials, compositions and methods thereof |
| CN102845416B (zh) * | 2011-07-01 | 2016-08-03 | 大日本除虫菊株式会社 | 芳香性防虫驱虫剂 |
| US8715753B1 (en) | 2011-10-13 | 2014-05-06 | Nadia Kolosova | Formulation for eliminating bedbugs |
| CA2855377C (en) * | 2011-11-09 | 2020-02-25 | Rutgers, The State University Of New Jersey | Bed bug lures |
| US20130209371A1 (en) * | 2012-02-15 | 2013-08-15 | Mark Anthony Willis | Germ Solve Candle |
| KR101349909B1 (ko) * | 2012-08-24 | 2014-01-16 | 한국생산기술연구원 | 함침법에 의한 방충소재 분말의 제조방법 |
| CN103548885A (zh) * | 2013-11-11 | 2014-02-05 | 福建省农业科学院植物保护研究所 | 土荆芥蚊香及其制备方法 |
| US10060074B2 (en) * | 2015-06-05 | 2018-08-28 | Romin Guard Corp. | Pest repellent fabric and fumigant for food |
| CN108697077B (zh) * | 2015-09-25 | 2022-04-19 | 组合块公司 | 多元醇、碳水化合物、核碱基和核苷组合物及其用途 |
| JP2017206493A (ja) * | 2016-05-17 | 2017-11-24 | アース製薬株式会社 | 伸縮性布帛用害虫忌避剤 |
| JP6588879B2 (ja) * | 2016-08-31 | 2019-10-09 | 花王株式会社 | 飛翔害虫忌避剤組成物 |
| ES2674263B1 (es) * | 2016-12-28 | 2019-04-02 | Zobele Espana Sa | Producto repelente de insectos |
| US10264787B1 (en) | 2017-11-28 | 2019-04-23 | BIOVECBLOK s.r.l. | Natural mosquito larvicide |
| US10306894B1 (en) | 2017-11-28 | 2019-06-04 | BIOVECBLOK s.r.l. | Natural mosquito repellant |
| BR112020012704A8 (pt) | 2017-12-21 | 2022-03-03 | Zymergen Inc | Nepetalactol oxidorredutases, nepetalactol sintases, e micróbios capazes de produzir nepetalactona |
| CN113226032B (zh) * | 2018-12-28 | 2023-01-03 | 花王株式会社 | 害虫驱避组合物 |
| SI3763212T1 (sl) * | 2019-07-11 | 2022-01-31 | Sanderstrothmann Gmbh | Sestava za odganjanje členonožcev |
| US10966424B1 (en) * | 2019-10-04 | 2021-04-06 | Global Biolife Inc. | Insect repelling composition |
| US12342828B2 (en) | 2020-09-14 | 2025-07-01 | Insight Pharmaceuticals Corporation | Repellant formulation and method |
| KR102349844B1 (ko) * | 2021-08-23 | 2022-01-10 | 한경대학교 산학협력단 | 방충 특성이 향상된 방충 조성물 및 이를 이용한 방충 스크린 |
| WO2023161674A1 (en) * | 2022-02-25 | 2023-08-31 | South Eastern University Of Sri Lanka | Repelling gel formulation comprising mint oil and citronellol, and methods of preparation thereof for management of palm weevils |
| US11653654B1 (en) | 2022-06-09 | 2023-05-23 | S. C. Johnson & Son, Inc. | Water-based insect repellent composition |
| US12295372B1 (en) | 2022-06-09 | 2025-05-13 | S. C. Johnson & Son, Inc. | Oil-based insect repellent composition |
| WO2024186653A2 (en) * | 2023-03-03 | 2024-09-12 | Entomol Products, Llc | Methods for making dihydronepetalactone and applications therefor |
| KR20250116934A (ko) | 2024-01-26 | 2025-08-04 | 국립금오공과대학교 산학협력단 | 네페탈락톤이 유효성분으로 포함된 캣닢 추출물을 함유하는 곤충 기피제 조성물 |
| US12378213B1 (en) | 2024-08-13 | 2025-08-05 | William Allen Boulanger | Process for the hydrogenation of catnip oil |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4869896A (en) | 1984-05-30 | 1989-09-26 | Angus Chemical Company | Potentiated insect repellent composition and method |
| US4663346A (en) * | 1984-05-30 | 1987-05-05 | Angus Chemical Company | Insect repellent |
| CA2042597A1 (en) | 1989-10-05 | 1991-04-06 | Yujiro Kojima | Cat attractant applying method and applicator |
| US5753686A (en) | 1992-09-18 | 1998-05-19 | International Flavors & Fragrances Inc. | Method for repelling fire ants and horn flies and compositions for repelling fire ants and horn flies and acting as anti-feedants for fire ants and horn flies |
| US6524605B1 (en) | 1999-08-06 | 2003-02-25 | Iowa State University Research Foundation, Inc. | Biorational repellents obtained from terpenoids for use against arthropods |
| JP2002145824A (ja) * | 2000-08-30 | 2002-05-22 | Mitsubishi Chemicals Corp | テレフタル酸の水素添加方法 |
| EP1192989A1 (de) * | 2000-09-28 | 2002-04-03 | Degussa AG | Katalysator zur Hydrierung aromatischer Nitroverbindungen |
| US6462015B1 (en) | 2000-11-10 | 2002-10-08 | International Flavors & Fragrances Inc. | Bicyclic lactones, perfumery uses thereof, processes for preparing same and intermediates therefor |
| JP2002316983A (ja) * | 2001-02-16 | 2002-10-31 | Kuraray Co Ltd | ２，５−ジヒドロキシ−１，４−ジオキサンの製造方法 |
| US6906108B2 (en) | 2001-08-17 | 2005-06-14 | Board Of Supervisors Of Louisiana State University And Agricultural And Mechanical College | Extracts of vetiver oil as repellent and toxicant to ants, ticks, and cockroaches |
| CN100396674C (zh) | 2002-01-23 | 2008-06-25 | 纳幕尔杜邦公司 | 芳香化合物 |
| WO2003086069A2 (en) | 2002-04-08 | 2003-10-23 | Jodi Haenke | Materials and methods for controlling wood-boring insects |
-
2003
- 2003-03-19 US US10/392,455 patent/US20030235601A1/en not_active Abandoned
- 2003-03-20 JP JP2003577629A patent/JP2005520837A/ja active Pending
- 2003-03-20 CN CNB038065533A patent/CN100521939C/zh not_active Expired - Lifetime
- 2003-03-20 KR KR10-2004-7014663A patent/KR20040097182A/ko not_active Ceased
- 2003-03-20 EP EP20030711652 patent/EP1484967B1/en not_active Expired - Lifetime
- 2003-03-20 BR BRPI0308639A patent/BRPI0308639B1/pt unknown
- 2003-03-20 ES ES03711652T patent/ES2397512T3/es not_active Expired - Lifetime
- 2003-03-20 WO PCT/US2003/008516 patent/WO2003079786A1/en not_active Ceased
- 2003-03-20 CA CA 2479123 patent/CA2479123C/en not_active Expired - Lifetime
- 2003-03-20 RU RU2004130863/04A patent/RU2004130863A/ru not_active Application Discontinuation
- 2003-03-20 HK HK05112098.1A patent/HK1079659A1/zh unknown
- 2003-03-20 MX MXPA04008994A patent/MXPA04008994A/es unknown
- 2003-03-20 AU AU2003214243A patent/AU2003214243B2/en not_active Ceased
- 2003-03-20 BR BR0308639A patent/BR0308639A/pt active IP Right Grant
-
2004
- 2004-08-04 ZA ZA200406233A patent/ZA200406233B/en unknown
- 2004-10-13 US US10/964,415 patent/US7232844B2/en not_active Expired - Lifetime
- 2004-10-27 US US10/974,863 patent/US20050112166A1/en not_active Abandoned
-
2007
- 2007-06-08 US US11/760,052 patent/US20070231357A1/en not_active Abandoned
Non-Patent Citations (4)
| Title |
|---|
| Cavill, GWK, et al: J.Insect Physiol, Vol.13, 1967, 131-135 * |
| Cavill, GWK, et al: Tetrahedron, Vol.38, 1982 1931-1938 * |
| Jefson, M et al: J. Chemical Ecology, Vol 9 , 1983, 159-180 * |
| Waller, G.R. et al: Proc. Olka. Acad. Sci. 64:49-56, 1984 * |
Also Published As
| Publication number | Publication date |
|---|---|
| BR0308639A (pt) | 2005-02-09 |
| CN1642420A (zh) | 2005-07-20 |
| US20070231357A1 (en) | 2007-10-04 |
| EP1484967A1 (en) | 2004-12-15 |
| AU2003214243A1 (en) | 2003-10-08 |
| MXPA04008994A (es) | 2004-12-07 |
| US7232844B2 (en) | 2007-06-19 |
| RU2004130863A (ru) | 2005-04-10 |
| WO2003079786A1 (en) | 2003-10-02 |
| US20050112166A1 (en) | 2005-05-26 |
| US20050069568A1 (en) | 2005-03-31 |
| CA2479123A1 (en) | 2003-10-02 |
| ZA200406233B (en) | 2006-06-28 |
| ES2397512T3 (es) | 2013-03-07 |
| BRPI0308639B1 (pt) | 2019-08-27 |
| CN100521939C (zh) | 2009-08-05 |
| HK1079659A1 (zh) | 2006-04-13 |
| EP1484967B1 (en) | 2012-10-24 |
| JP2005520837A (ja) | 2005-07-14 |
| US20030235601A1 (en) | 2003-12-25 |
| KR20040097182A (ko) | 2004-11-17 |
| CA2479123C (en) | 2013-02-12 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| AU2003214243B2 (en) | Dihydronepetalactone as insect repellent | |
| US8633325B2 (en) | Method for making insect repellent composition | |
| CA2584354C (en) | Insect repellent compositions comprising dihydronepetalactone, an alcohol and an ester | |
| CA2538363C (en) | Insect repellent compositions comprising dihydronepetalactone | |
| JP2008526770A (ja) | ネペタラクタムおよびそのｎ−置換誘導体 | |
| AU2006297162A2 (en) | Puleganic acid insect repellents | |
| US20040127553A1 (en) | Insect repellent compositions comprising dihydronepetalactone | |
| JP2008526769A (ja) | ジヒドロネペタラクタムおよびそのｎ−置換誘導体 | |
| US20130165506A1 (en) | Puleganic acid insect repellent | |
| KR20060089208A (ko) | 디히드로네페타락톤을 포함하는 방충제 조성물 | |
| US7776912B2 (en) | Acetals of nepetalic acid and method of preparation |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FGA | Letters patent sealed or granted (standard patent) | ||
| MK14 | Patent ceased section 143(a) (annual fees not paid) or expired |