JP2005082559A5 - - Google Patents
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- Publication number
- JP2005082559A5 JP2005082559A5 JP2003318779A JP2003318779A JP2005082559A5 JP 2005082559 A5 JP2005082559 A5 JP 2005082559A5 JP 2003318779 A JP2003318779 A JP 2003318779A JP 2003318779 A JP2003318779 A JP 2003318779A JP 2005082559 A5 JP2005082559 A5 JP 2005082559A5
- Authority
- JP
- Japan
- Prior art keywords
- beetle
- long
- sex
- stimulant
- horned
- 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.)
- Granted
Links
- 150000001875 compounds Chemical class 0.000 claims description 66
- 241000254173 Coleoptera Species 0.000 claims description 47
- 241000244615 Ergates faber Species 0.000 claims description 35
- 239000004480 active ingredient Substances 0.000 claims description 33
- 239000000463 material Substances 0.000 claims description 26
- COKUIQKSCLYMNN-UHFFFAOYSA-N 4-methyloctacosane Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCC(C)CCC COKUIQKSCLYMNN-UHFFFAOYSA-N 0.000 claims description 20
- BJQWYEJQWHSSCJ-UHFFFAOYSA-N Heptacosane Natural products CCCCCCCCCCCCCCCCCCCCCCCCCCC BJQWYEJQWHSSCJ-UHFFFAOYSA-N 0.000 claims description 20
- OLTHARGIAFTREU-UHFFFAOYSA-N 9-methylnonacosane Chemical compound CCCCCCCCCCCCCCCCCCCCC(C)CCCCCCCC OLTHARGIAFTREU-UHFFFAOYSA-N 0.000 claims description 13
- 230000000749 insecticidal effect Effects 0.000 claims description 13
- IGGUPRCHHJZPBS-UHFFFAOYSA-N nonacosane Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCCC IGGUPRCHHJZPBS-UHFFFAOYSA-N 0.000 claims description 13
- 239000002038 ethyl acetate fraction Substances 0.000 claims description 11
- UPXMLPKPQMWALZ-UHFFFAOYSA-N 15-methylhentriacontane Chemical compound CCCCCCCCCCCCCCCCC(C)CCCCCCCCCCCCCC UPXMLPKPQMWALZ-UHFFFAOYSA-N 0.000 claims description 10
- RWVONPYEUYBBJH-UHFFFAOYSA-N 4-methylhexacosane Chemical compound CCCCCCCCCCCCCCCCCCCCCCC(C)CCC RWVONPYEUYBBJH-UHFFFAOYSA-N 0.000 claims description 9
- OKQGOONCABNXHR-UHFFFAOYSA-N 15-methyltritriacontane Chemical compound CCCCCCCCCCCCCCCCCCC(C)CCCCCCCCCCCCCC OKQGOONCABNXHR-UHFFFAOYSA-N 0.000 claims description 8
- RLCPPUWUVWSWRU-UHFFFAOYSA-N 9-methylheptacosane Chemical compound CCCCCCCCCCCCCCCCCCC(C)CCCCCCCC RLCPPUWUVWSWRU-UHFFFAOYSA-N 0.000 claims description 8
- BDRZUARQSWNWBO-UHFFFAOYSA-N heptacosan-10-one Chemical compound CCCCCCCCCCCCCCCCCC(=O)CCCCCCCCC BDRZUARQSWNWBO-UHFFFAOYSA-N 0.000 claims description 8
- 239000011521 glass Substances 0.000 claims description 7
- IEMOMXGXBOVRLW-HDXUUTQWSA-N (18z,21z)-heptacosa-18,21-dien-10-one Chemical compound CCCCCCCCCC(=O)CCCCCCC\C=C/C\C=C/CCCCC IEMOMXGXBOVRLW-HDXUUTQWSA-N 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 239000004744 fabric Substances 0.000 claims description 5
- 239000007903 gelatin capsule Substances 0.000 claims description 5
- 239000002184 metal Substances 0.000 claims description 5
- MLKYJOAUVPJTPH-BBDKIWCZSA-N (18z,21z,24z)-heptacosa-18,21,24-trien-10-one Chemical compound CCCCCCCCCC(=O)CCCCCCC\C=C/C\C=C/C\C=C/CC MLKYJOAUVPJTPH-BBDKIWCZSA-N 0.000 claims description 3
- 229940125904 compound 1 Drugs 0.000 claims description 3
- 239000000284 extract Substances 0.000 claims description 3
- 230000001568 sexual effect Effects 0.000 claims description 3
- 241001174997 Lymexylon navale Species 0.000 claims description 2
- 241000255925 Diptera Species 0.000 claims 1
- 241000276707 Tilapia Species 0.000 claims 1
- 239000012259 ether extract Substances 0.000 claims 1
- VSDSMPLLDJUGIM-UHFFFAOYSA-N heptacos-18-en-10-one Chemical compound CCCCCCCCCC(=O)CCCCCCCC=CCCCCCCCC VSDSMPLLDJUGIM-UHFFFAOYSA-N 0.000 claims 1
- 239000000077 insect repellent Substances 0.000 claims 1
- 239000013543 active substance Substances 0.000 description 29
- 239000000126 substance Substances 0.000 description 28
- 0 CC(CC1CC2CC2)C(*)([C@@](C)C(C2CC2)[C@@]2C3C2)C1(C1CC1)C3(*)C1**1 Chemical compound CC(CC1CC2CC2)C(*)([C@@](C)C(C2CC2)[C@@]2C3C2)C1(C1CC1)C3(*)C1**1 0.000 description 27
- 230000000694 effects Effects 0.000 description 22
- 241000607479 Yersinia pestis Species 0.000 description 13
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 13
- 238000001228 spectrum Methods 0.000 description 13
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- 239000002243 precursor Substances 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 238000005481 NMR spectroscopy Methods 0.000 description 9
- 229930195733 hydrocarbon Natural products 0.000 description 9
- 150000002430 hydrocarbons Chemical class 0.000 description 9
- 239000003016 pheromone Substances 0.000 description 9
- VSDSMPLLDJUGIM-PFONDFGASA-N (z)-heptacos-18-en-10-one Chemical compound CCCCCCCCCC(=O)CCCCCCC\C=C/CCCCCCCC VSDSMPLLDJUGIM-PFONDFGASA-N 0.000 description 6
- 230000000844 anti-bacterial effect Effects 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 150000002576 ketones Chemical class 0.000 description 6
- 150000002611 lead compounds Chemical class 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- 239000002917 insecticide Substances 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 241000238631 Hexapoda Species 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 229940126214 compound 3 Drugs 0.000 description 4
- 238000004128 high performance liquid chromatography Methods 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 239000000021 stimulant Substances 0.000 description 4
- 230000004936 stimulating effect Effects 0.000 description 4
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 3
- 239000000877 Sex Attractant Substances 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 235000019441 ethanol Nutrition 0.000 description 3
- 239000002044 hexane fraction Substances 0.000 description 3
- 238000002955 isolation Methods 0.000 description 3
- 239000005871 repellent Substances 0.000 description 3
- 230000002940 repellent Effects 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- ILFPCMXTASDZKM-YFKPBYRVSA-N (1s)-2-methylidene-3-oxocyclopentane-1-carboxylic acid Chemical compound OC(=O)[C@H]1CCC(=O)C1=C ILFPCMXTASDZKM-YFKPBYRVSA-N 0.000 description 2
- SPZXGRZMQWESTC-UHFFFAOYSA-N 3,3a,4,5,6,6a-hexahydro-1h-cyclopenta[c]furan Chemical group C1OCC2CCCC21 SPZXGRZMQWESTC-UHFFFAOYSA-N 0.000 description 2
- 241000196324 Embryophyta Species 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 239000003905 agrochemical Substances 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 230000003115 biocidal effect Effects 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 229940125782 compound 2 Drugs 0.000 description 2
- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 238000011835 investigation Methods 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 230000001681 protective effect Effects 0.000 description 2
- 230000010539 reproductive behavior Effects 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- ILFPCMXTASDZKM-UHFFFAOYSA-N sarkomycin Natural products OC(=O)C1CCC(=O)C1=C ILFPCMXTASDZKM-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- -1 (18Z Chemical compound 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- 241000751139 Beauveria bassiana Species 0.000 description 1
- JGUCQXWFKVVIFK-ALCCZGGFSA-N CC(C1)C#C/C1=C/S Chemical compound CC(C1)C#C/C1=C/S JGUCQXWFKVVIFK-ALCCZGGFSA-N 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 1
- BZKFMUIJRXWWQK-UHFFFAOYSA-N Cyclopentenone Chemical compound O=C1CCC=C1 BZKFMUIJRXWWQK-UHFFFAOYSA-N 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 241000233866 Fungi Species 0.000 description 1
- 206010024229 Leprosy Diseases 0.000 description 1
- 229930189782 Methylenomycin Natural products 0.000 description 1
- 241000123069 Ocyurus chrysurus Species 0.000 description 1
- 244000115721 Pennisetum typhoides Species 0.000 description 1
- 235000007195 Pennisetum typhoides Nutrition 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 235000006485 Platanus occidentalis Nutrition 0.000 description 1
- 244000268528 Platanus occidentalis Species 0.000 description 1
- 241000149489 Rhipiceridae Species 0.000 description 1
- 235000008515 Setaria glauca Nutrition 0.000 description 1
- 230000003187 abdominal effect Effects 0.000 description 1
- 239000012190 activator Substances 0.000 description 1
- 125000003158 alcohol group Chemical group 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 230000000259 anti-tumor effect Effects 0.000 description 1
- 238000011914 asymmetric synthesis Methods 0.000 description 1
- 230000006399 behavior Effects 0.000 description 1
- 230000000975 bioactive effect Effects 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 238000002983 circular dichroism Methods 0.000 description 1
- 235000020971 citrus fruits Nutrition 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 238000004891 communication Methods 0.000 description 1
- 230000007123 defense Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 235000013601 eggs Nutrition 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 244000053095 fungal pathogen Species 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 239000002085 irritant Substances 0.000 description 1
- 231100000021 irritant Toxicity 0.000 description 1
- 150000002596 lactones Chemical class 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 230000013011 mating Effects 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 239000002728 pyrethroid Substances 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000012916 structural analysis Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- JXTPJDDICSTXJX-UHFFFAOYSA-N triacontane Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCCCC JXTPJDDICSTXJX-UHFFFAOYSA-N 0.000 description 1
- 238000000870 ultraviolet spectroscopy Methods 0.000 description 1
- 125000004417 unsaturated alkyl group Chemical group 0.000 description 1
- 238000004804 winding Methods 0.000 description 1
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2003318779A JP4621904B2 (ja) | 2003-09-10 | 2003-09-10 | 光学活性な３−オキサビシクロ［３．３．０］オクタン骨格を有する化合物およびその使用 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2003318779A JP4621904B2 (ja) | 2003-09-10 | 2003-09-10 | 光学活性な３−オキサビシクロ［３．３．０］オクタン骨格を有する化合物およびその使用 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2005082559A JP2005082559A (ja) | 2005-03-31 |
| JP2005082559A5 true JP2005082559A5 (enExample) | 2006-09-21 |
| JP4621904B2 JP4621904B2 (ja) | 2011-02-02 |
Family
ID=34417966
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2003318779A Expired - Lifetime JP4621904B2 (ja) | 2003-09-10 | 2003-09-10 | 光学活性な３−オキサビシクロ［３．３．０］オクタン骨格を有する化合物およびその使用 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP4621904B2 (enExample) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104328153A (zh) * | 2014-10-13 | 2015-02-04 | 青岛科技大学 | 一种细胞法生产手性烯醇的方法 |
| JP7630155B2 (ja) * | 2020-12-15 | 2025-02-17 | 国立研究開発法人農業・食品産業技術総合研究機構 | カミキリムシ科昆虫の防除方法 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP3079259B2 (ja) * | 1997-09-10 | 2000-08-21 | 農林水産省蚕糸・昆虫農業技術研究所長 | ゴマダラカミキリの性刺激剤 |
-
2003
- 2003-09-10 JP JP2003318779A patent/JP4621904B2/ja not_active Expired - Lifetime
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