AU2003240349B2 - Insect repellents - Google Patents
Insect repellents Download PDFInfo
- Publication number
- AU2003240349B2 AU2003240349B2 AU2003240349A AU2003240349A AU2003240349B2 AU 2003240349 B2 AU2003240349 B2 AU 2003240349B2 AU 2003240349 A AU2003240349 A AU 2003240349A AU 2003240349 A AU2003240349 A AU 2003240349A AU 2003240349 B2 AU2003240349 B2 AU 2003240349B2
- Authority
- AU
- Australia
- Prior art keywords
- menthyl ester
- ester
- carbamic acid
- group
- compound
- 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
- 239000000077 insect repellent Substances 0.000 title claims description 22
- 150000001875 compounds Chemical class 0.000 claims description 57
- 239000000203 mixture Substances 0.000 claims description 39
- 241000238631 Hexapoda Species 0.000 claims description 19
- -1 amino- Chemical class 0.000 claims description 10
- 229910052757 nitrogen Inorganic materials 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- 125000005842 heteroatom Chemical group 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 7
- 229910052717 sulfur Inorganic materials 0.000 claims description 7
- 125000001931 aliphatic group Chemical group 0.000 claims description 6
- 125000003118 aryl group Chemical group 0.000 claims description 6
- 150000002148 esters Chemical class 0.000 claims description 6
- 125000001072 heteroaryl group Chemical group 0.000 claims description 6
- 239000002917 insecticide Substances 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- 239000003205 fragrance Substances 0.000 claims description 5
- IEVVHMTWFAUOKJ-UHFFFAOYSA-N (5-methyl-2-propan-2-ylcyclohexyl) n,n-diethylcarbamate Chemical compound CCN(CC)C(=O)OC1CC(C)CCC1C(C)C IEVVHMTWFAUOKJ-UHFFFAOYSA-N 0.000 claims description 4
- OGWAITVDDYTMRF-UHFFFAOYSA-N (5-methyl-2-propan-2-ylcyclohexyl) n-(2-methylpropyl)carbamate Chemical compound CC(C)CNC(=O)OC1CC(C)CCC1C(C)C OGWAITVDDYTMRF-UHFFFAOYSA-N 0.000 claims description 4
- 239000004615 ingredient Substances 0.000 claims description 4
- OSMGKYGOMMKPIY-UHFFFAOYSA-N (5-methyl-2-propan-2-ylcyclohexyl) morpholine-4-carboxylate Chemical compound CC(C)C1CCC(C)CC1OC(=O)N1CCOCC1 OSMGKYGOMMKPIY-UHFFFAOYSA-N 0.000 claims description 3
- JPMPMMKIDZNAEX-UHFFFAOYSA-N (5-methyl-2-propan-2-ylcyclohexyl) n-butylcarbamate Chemical compound CCCCNC(=O)OC1CC(C)CCC1C(C)C JPMPMMKIDZNAEX-UHFFFAOYSA-N 0.000 claims description 3
- MFECVIRCZJLBCY-UHFFFAOYSA-N (5-methyl-2-propan-2-ylcyclohexyl) n-methylcarbamate Chemical compound CNC(=O)OC1CC(C)CCC1C(C)C MFECVIRCZJLBCY-UHFFFAOYSA-N 0.000 claims description 3
- CDPKAQDTIGYJOH-UHFFFAOYSA-N 3-[(5-methyl-2-propan-2-ylcyclohexyl)oxycarbonylamino]propanoic acid Chemical compound CC(C)C1CCC(C)CC1OC(=O)NCCC(O)=O CDPKAQDTIGYJOH-UHFFFAOYSA-N 0.000 claims description 3
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000003368 amide group Chemical group 0.000 claims description 3
- 125000004104 aryloxy group Chemical group 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
- 230000001846 repelling effect Effects 0.000 claims description 3
- HDPFJNHRRLYGLW-UHFFFAOYSA-N (5-methyl-2-propan-2-ylcyclohexyl) n-phenylcarbamate Chemical compound CC(C)C1CCC(C)CC1OC(=O)NC1=CC=CC=C1 HDPFJNHRRLYGLW-UHFFFAOYSA-N 0.000 claims description 2
- ZMBIWMANKXBTLA-UHFFFAOYSA-N (5-methyl-2-propan-2-ylcyclohexyl) piperidine-1-carboxylate Chemical compound CC(C)C1CCC(C)CC1OC(=O)N1CCCCC1 ZMBIWMANKXBTLA-UHFFFAOYSA-N 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 239000000758 substrate Substances 0.000 claims description 2
- JQFDIOKZPWALRI-UHFFFAOYSA-N (5-methyl-2-propan-2-ylcyclohexyl) n-ethylcarbamate Chemical compound CCNC(=O)OC1CC(C)CCC1C(C)C JQFDIOKZPWALRI-UHFFFAOYSA-N 0.000 claims 1
- RCKGVDDTPDZBFZ-UHFFFAOYSA-N (5-methyl-2-propan-2-ylcyclohexyl) pyrrolidine-1-carboxylate Chemical compound CC(C)C1CCC(C)CC1OC(=O)N1CCCC1 RCKGVDDTPDZBFZ-UHFFFAOYSA-N 0.000 claims 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 21
- 241001674044 Blattodea Species 0.000 description 12
- 230000008878 coupling Effects 0.000 description 10
- 238000010168 coupling process Methods 0.000 description 10
- 238000005859 coupling reaction Methods 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 239000000047 product Substances 0.000 description 8
- 238000005160 1H NMR spectroscopy Methods 0.000 description 7
- 230000000694 effects Effects 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 241000238657 Blattella germanica Species 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 239000002304 perfume Substances 0.000 description 5
- 239000005871 repellent Substances 0.000 description 5
- 230000002940 repellent Effects 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- NIQCNGHVCWTJSM-UHFFFAOYSA-N Dimethyl phthalate Chemical compound COC(=O)C1=CC=CC=C1C(=O)OC NIQCNGHVCWTJSM-UHFFFAOYSA-N 0.000 description 4
- 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 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 230000005923 long-lasting effect Effects 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- NOOLISFMXDJSKH-KXUCPTDWSA-N (-)-Menthol Chemical compound CC(C)[C@@H]1CC[C@@H](C)C[C@H]1O NOOLISFMXDJSKH-KXUCPTDWSA-N 0.000 description 3
- SLIAVDGEVKKHIC-UHFFFAOYSA-N (5-methyl-2-propan-2-ylcyclohexyl) carbamate Chemical class CC(C)C1CCC(C)CC1OC(N)=O SLIAVDGEVKKHIC-UHFFFAOYSA-N 0.000 description 3
- 241000255925 Diptera Species 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- 229960001673 diethyltoluamide Drugs 0.000 description 3
- 244000144972 livestock Species 0.000 description 3
- 239000000344 soap Substances 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 241000238876 Acari Species 0.000 description 2
- NOOLISFMXDJSKH-UHFFFAOYSA-N DL-menthol Natural products CC(C)C1CCC(C)CC1O NOOLISFMXDJSKH-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- 201000006353 Filariasis Diseases 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 241000257303 Hymenoptera Species 0.000 description 2
- 206010061217 Infestation Diseases 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- 244000302151 Myroxylon pereirae Species 0.000 description 2
- 235000014150 Myroxylon pereirae Nutrition 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 244000007731 Tolu balsam tree Species 0.000 description 2
- 235000007423 Tolu balsam tree Nutrition 0.000 description 2
- 241000256856 Vespidae Species 0.000 description 2
- 241000607479 Yersinia pestis Species 0.000 description 2
- ZDKZHVNKFOXMND-UHFFFAOYSA-N cis-Nepetalactone Natural products O=C1OC=C(C)C2C1C(C)CC2 ZDKZHVNKFOXMND-UHFFFAOYSA-N 0.000 description 2
- 239000010632 citronella oil Substances 0.000 description 2
- FLKPEMZONWLCSK-UHFFFAOYSA-N diethyl phthalate Chemical compound CCOC(=O)C1=CC=CC=C1C(=O)OCC FLKPEMZONWLCSK-UHFFFAOYSA-N 0.000 description 2
- FBSAITBEAPNWJG-UHFFFAOYSA-N dimethyl phthalate Natural products CC(=O)OC1=CC=CC=C1OC(C)=O FBSAITBEAPNWJG-UHFFFAOYSA-N 0.000 description 2
- 229960001826 dimethylphthalate Drugs 0.000 description 2
- 206010014599 encephalitis Diseases 0.000 description 2
- 239000004744 fabric Substances 0.000 description 2
- 239000000796 flavoring agent Substances 0.000 description 2
- 235000019634 flavors Nutrition 0.000 description 2
- 229940041616 menthol Drugs 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 239000002453 shampoo Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 239000001993 wax Substances 0.000 description 2
- KIUPCUCGVCGPPA-UHFFFAOYSA-N (5-methyl-2-propan-2-ylcyclohexyl) carbonochloridate Chemical compound CC(C)C1CCC(C)CC1OC(Cl)=O KIUPCUCGVCGPPA-UHFFFAOYSA-N 0.000 description 1
- DSSYKIVIOFKYAU-XCBNKYQSSA-N (R)-camphor Chemical compound C1C[C@@]2(C)C(=O)C[C@@H]1C2(C)C DSSYKIVIOFKYAU-XCBNKYQSSA-N 0.000 description 1
- ODHCTXKNWHHXJC-VKHMYHEASA-N 5-oxo-L-proline Chemical compound OC(=O)[C@@H]1CCC(=O)N1 ODHCTXKNWHHXJC-VKHMYHEASA-N 0.000 description 1
- 241000256111 Aedes <genus> Species 0.000 description 1
- 241000256118 Aedes aegypti Species 0.000 description 1
- 241000256186 Anopheles <genus> Species 0.000 description 1
- 241000239223 Arachnida Species 0.000 description 1
- 241000239290 Araneae Species 0.000 description 1
- 241000238658 Blattella Species 0.000 description 1
- 101150041968 CDC13 gene Proteins 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 1
- 241000723346 Cinnamomum camphora Species 0.000 description 1
- 241000256054 Culex <genus> Species 0.000 description 1
- 208000001490 Dengue Diseases 0.000 description 1
- 206010012310 Dengue fever Diseases 0.000 description 1
- 206010052804 Drug tolerance Diseases 0.000 description 1
- 206010014612 Encephalitis viral Diseases 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 244000166124 Eucalyptus globulus Species 0.000 description 1
- 229920006358 Fluon Polymers 0.000 description 1
- 241000282412 Homo Species 0.000 description 1
- 241001124553 Lepismatidae Species 0.000 description 1
- 229920000877 Melamine resin Polymers 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- JLNGEXDJAQASHD-UHFFFAOYSA-N N,N-Diethylbenzamide Chemical compound CCN(CC)C(=O)C1=CC=CC=C1 JLNGEXDJAQASHD-UHFFFAOYSA-N 0.000 description 1
- 240000009215 Nepeta cataria Species 0.000 description 1
- 235000010679 Nepeta cataria Nutrition 0.000 description 1
- 241000258242 Siphonaptera Species 0.000 description 1
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 1
- 208000003152 Yellow Fever Diseases 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
- 239000004599 antimicrobial Substances 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 235000006708 antioxidants Nutrition 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 238000004166 bioassay Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 229960000846 camphor Drugs 0.000 description 1
- 229930008380 camphor Natural products 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- FZFAMSAMCHXGEF-UHFFFAOYSA-N chloro formate Chemical group ClOC=O FZFAMSAMCHXGEF-UHFFFAOYSA-N 0.000 description 1
- AOGYCOYQMAVAFD-UHFFFAOYSA-N chlorocarbonic acid Chemical class OC(Cl)=O AOGYCOYQMAVAFD-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000012790 confirmation Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 239000010639 cypress oil Substances 0.000 description 1
- 208000025729 dengue disease Diseases 0.000 description 1
- 239000002781 deodorant agent Substances 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000003292 diminished effect Effects 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 230000008029 eradication Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- KWBIXTIBYFUAGV-UHFFFAOYSA-N ethylcarbamic acid Chemical compound CCNC(O)=O KWBIXTIBYFUAGV-UHFFFAOYSA-N 0.000 description 1
- 239000010642 eucalyptus oil Substances 0.000 description 1
- 229940044949 eucalyptus oil Drugs 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 239000003925 fat Substances 0.000 description 1
- 239000001148 ferula galbaniflua oil terpeneless Substances 0.000 description 1
- 229920002313 fluoropolymer Polymers 0.000 description 1
- 239000004811 fluoropolymer Substances 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- IVJISJACKSSFGE-UHFFFAOYSA-N formaldehyde;1,3,5-triazine-2,4,6-triamine Chemical compound O=C.NC1=NC(N)=NC(N)=N1 IVJISJACKSSFGE-UHFFFAOYSA-N 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 230000026781 habituation Effects 0.000 description 1
- 231100000206 health hazard Toxicity 0.000 description 1
- 239000003752 hydrotrope Substances 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000006193 liquid solution Substances 0.000 description 1
- 239000006210 lotion Substances 0.000 description 1
- 201000004792 malaria Diseases 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000001105 regulatory effect Effects 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
- 230000035945 sensitivity Effects 0.000 description 1
- 239000002884 skin cream Substances 0.000 description 1
- 238000002791 soaking Methods 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 230000000475 sunscreen effect Effects 0.000 description 1
- 239000000516 sunscreening agent Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 201000002498 viral encephalitis Diseases 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 238000010626 work up procedure 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
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
- A01N47/20—N-Aryl derivatives thereof
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
- A01N47/18—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing a —O—CO—N< group, or a thio analogue thereof, directly attached to a heterocyclic or cycloaliphatic ring
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Dentistry (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Agronomy & Crop Science (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB0214342.8 | 2002-06-21 | ||
| GBGB0214342.8A GB0214342D0 (en) | 2002-06-21 | 2002-06-21 | Insect repellents |
| PCT/CH2003/000403 WO2004000023A1 (en) | 2002-06-21 | 2003-06-20 | Insect repellents |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU2003240349A1 AU2003240349A1 (en) | 2004-01-06 |
| AU2003240349B2 true AU2003240349B2 (en) | 2008-03-06 |
Family
ID=9939035
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2003240349A Ceased AU2003240349B2 (en) | 2002-06-21 | 2003-06-20 | Insect repellents |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US20060063764A1 (https=) |
| EP (1) | EP1515610A1 (https=) |
| JP (1) | JP2006504638A (https=) |
| CN (1) | CN100338034C (https=) |
| AU (1) | AU2003240349B2 (https=) |
| BR (1) | BR0312156A (https=) |
| GB (1) | GB0214342D0 (https=) |
| MX (1) | MXPA04012203A (https=) |
| WO (1) | WO2004000023A1 (https=) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MXPA05010888A (es) * | 2003-04-14 | 2005-11-25 | Givaudan Sa | Carbamatos usados como fragancias. |
| EP2064959B1 (de) * | 2007-10-31 | 2012-07-25 | Symrise AG | Aromatische Neo-Menthylamide als Geschmacksstoffe |
| US8911715B2 (en) * | 2008-05-30 | 2014-12-16 | Symrise Ag | L-menthyl-N-(2-hydroxyphenyl)carbamate |
| EP2135516B1 (de) * | 2008-06-13 | 2012-08-15 | Symrise AG | Neo-Menthylderivate als Geschmacksstoffe |
| EP3115045B1 (de) | 2008-08-26 | 2020-08-12 | Basf Se | Nachweis und verwendung niedermolekularer modulatoren des kälte-menthol-rezeptors trpm8 |
| JP5550717B2 (ja) * | 2009-04-01 | 2014-07-16 | コルゲート・パーモリブ・カンパニー | メントール誘導体ならびに口腔活性剤および全身活性剤としてのそれらの使用 |
| DE102010002558A1 (de) | 2009-11-20 | 2011-06-01 | Symrise Ag | Verwendung physiologischer Kühlwirkstoffe und Mittel enthaltend solche Wirkstoffe |
| EP2389922A1 (en) | 2010-05-25 | 2011-11-30 | Symrise AG | Cyclohexyl carbamate compounds as anti-ageing actives |
| US20110294876A1 (en) * | 2010-05-25 | 2011-12-01 | Symrise Ag | Cyclohexyl carbamate compounds as anti-ageing actives |
| US9029415B2 (en) | 2010-06-14 | 2015-05-12 | Symrise Ag | Cooling mixtures with an enhanced cooling effect of 5-methyl-2-(propane-2-yl)cyclohexyl-N-ethyloxamate |
| EP2394703B1 (de) | 2010-06-14 | 2015-12-23 | Symrise AG | Kühlmischungen mit verstärkter Kühlwirkung von 5-Methyl-2-(propan-2-yl)cyclohexyl-N-ethyloxamat |
| WO2012083190A1 (en) * | 2010-12-17 | 2012-06-21 | The Rockefeller University | Insect odorant receptor antagonists |
| WO2013041621A1 (de) | 2011-09-20 | 2013-03-28 | Basf Se | Niedermolekulare modulatoren des kälte-menthol-rezeptors trpm8 und deren verwendung |
| WO2014095541A1 (en) | 2012-12-20 | 2014-06-26 | Henkel Ag & Co. Kgaa | Insect repellent cleaning composition |
| EP3675809B1 (de) | 2017-08-31 | 2023-09-27 | Basf Se | Verwendung physiologischer kühlwirkstoffe und mittel enthaltend solche wirkstoffe |
| CN119486725A (zh) | 2022-07-11 | 2025-02-18 | 西姆莱斯有限公司 | (2e)-3-(1,3-苯并二氧杂环戊烯-5-基)-n-苯基-n-(四氢-3-呋喃基)-2-丙烯酰胺的混合物和用途 |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| DE1300725B (de) * | 1962-06-23 | 1969-08-07 | Schering Ag | Insektizide synergistische Gemische |
| DE1792331C3 (de) * | 1962-06-23 | 1974-01-10 | Schering Ag, 1000 Berlin Und 4619 Bergkamen | Insektizide synergistische Gemische. Ausscheidung aus: 1300725 |
| DE1518713B1 (de) * | 1965-07-13 | 1971-01-14 | Degussa | Verfahren zur Herstellung von Terpenestern |
| JPS60199804A (ja) * | 1984-03-26 | 1985-10-09 | Nippon Kayaku Co Ltd | 有害生物忌避剤 |
| US5182305A (en) * | 1986-08-08 | 1993-01-26 | Colgate-Palmolive Co. | N-aryl and n-cycloakyl neoalkanamide insect repellents |
| US5391578A (en) * | 1986-08-08 | 1995-02-21 | Colgate-Palmolive Co. | N-lower alkyl neoalkanamide insect repellents |
| JP2979062B2 (ja) * | 1990-12-26 | 1999-11-15 | 大日本除蟲菊株式会社 | ダニ忌避性寝具 |
| US6150415A (en) * | 1996-08-13 | 2000-11-21 | The Regents Of The University Of California | Epoxide hydrolase complexes and methods therewith |
| GB9820233D0 (en) * | 1998-09-18 | 1998-11-11 | Quest Int | Improvements in or relating to insect repellents |
| BRPI0113421B8 (pt) * | 2000-08-24 | 2016-05-10 | Givaudan Sa | uso de compostos p-mentano carboxamidas n-substituídas como repelente de insetos |
-
2002
- 2002-06-21 GB GBGB0214342.8A patent/GB0214342D0/en not_active Ceased
-
2003
- 2003-06-20 JP JP2004514505A patent/JP2006504638A/ja active Pending
- 2003-06-20 MX MXPA04012203A patent/MXPA04012203A/es active IP Right Grant
- 2003-06-20 US US10/518,730 patent/US20060063764A1/en not_active Abandoned
- 2003-06-20 AU AU2003240349A patent/AU2003240349B2/en not_active Ceased
- 2003-06-20 WO PCT/CH2003/000403 patent/WO2004000023A1/en not_active Ceased
- 2003-06-20 BR BR0312156-9A patent/BR0312156A/pt not_active IP Right Cessation
- 2003-06-20 EP EP03729765A patent/EP1515610A1/en not_active Withdrawn
- 2003-06-20 CN CNB038143895A patent/CN100338034C/zh not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| BR0312156A (pt) | 2005-03-29 |
| CN1662141A (zh) | 2005-08-31 |
| GB0214342D0 (en) | 2002-07-31 |
| WO2004000023A1 (en) | 2003-12-31 |
| AU2003240349A1 (en) | 2004-01-06 |
| CN100338034C (zh) | 2007-09-19 |
| US20060063764A1 (en) | 2006-03-23 |
| MXPA04012203A (es) | 2005-02-25 |
| JP2006504638A (ja) | 2006-02-09 |
| EP1515610A1 (en) | 2005-03-23 |
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