JPH0212463B2 - - Google Patents
Info
- Publication number
- JPH0212463B2 JPH0212463B2 JP59255202A JP25520284A JPH0212463B2 JP H0212463 B2 JPH0212463 B2 JP H0212463B2 JP 59255202 A JP59255202 A JP 59255202A JP 25520284 A JP25520284 A JP 25520284A JP H0212463 B2 JPH0212463 B2 JP H0212463B2
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- tetradecenoate
- mixture
- column
- purified
- 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.)
- Expired - Lifetime
Links
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims description 6
- WAFYJSDEQGSUTH-UHFFFAOYSA-N methyl tetradec-5-enoate Chemical compound CCCCCCCCC=CCCCC(=O)OC WAFYJSDEQGSUTH-UHFFFAOYSA-N 0.000 claims description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 3
- AYMUQTNXKPEMLM-UHFFFAOYSA-N 1-bromononane Chemical compound CCCCCCCCCBr AYMUQTNXKPEMLM-UHFFFAOYSA-N 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- RAVVJKCSZXAIQP-UHFFFAOYSA-N methyl 5-bromopentanoate Chemical compound COC(=O)CCCCBr RAVVJKCSZXAIQP-UHFFFAOYSA-N 0.000 claims description 2
- NJXRQGKTLWXMID-UHFFFAOYSA-M nonyl(triphenyl)phosphanium;bromide Chemical compound [Br-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(CCCCCCCCC)C1=CC=CC=C1 NJXRQGKTLWXMID-UHFFFAOYSA-M 0.000 claims description 2
- YBTZROCKNUIONO-UHFFFAOYSA-N methyl 5-oxopentanoate Chemical compound COC(=O)CCCC=O YBTZROCKNUIONO-UHFFFAOYSA-N 0.000 claims 2
- MHWZOGBPWJSNRX-UHFFFAOYSA-N CCCCCCCCCC(C=CC=C1)=C1P(C1=CC=CC=C1)C1=CC=CC=C1.Br Chemical compound CCCCCCCCCC(C=CC=C1)=C1P(C1=CC=CC=C1)C1=CC=CC=C1.Br MHWZOGBPWJSNRX-UHFFFAOYSA-N 0.000 claims 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 15
- 239000000203 mixture Substances 0.000 description 12
- 241000254173 Coleoptera Species 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- 241000238631 Hexapoda Species 0.000 description 7
- 239000000877 Sex Attractant Substances 0.000 description 7
- 241000607479 Yersinia pestis Species 0.000 description 7
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- XGQJZNCFDLXSIJ-UHFFFAOYSA-N pentadecanal Chemical compound CCCCCCCCCCCCCCC=O XGQJZNCFDLXSIJ-UHFFFAOYSA-N 0.000 description 6
- 239000005667 attractant Substances 0.000 description 5
- 230000031902 chemoattractant activity Effects 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- WAFYJSDEQGSUTH-KHPPLWFESA-N methyl (z)-tetradec-5-enoate Chemical group CCCCCCCC\C=C/CCCC(=O)OC WAFYJSDEQGSUTH-KHPPLWFESA-N 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 229920000742 Cotton Polymers 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
- 239000013543 active substance Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 241000894007 species Species 0.000 description 4
- FKHIFSZMMVMEQY-UHFFFAOYSA-N talc Chemical compound [Mg+2].[O-][Si]([O-])=O FKHIFSZMMVMEQY-UHFFFAOYSA-N 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 239000004480 active ingredient Substances 0.000 description 3
- 239000012876 carrier material Substances 0.000 description 3
- 238000004440 column chromatography Methods 0.000 description 3
- 230000003247 decreasing effect Effects 0.000 description 3
- 235000019387 fatty acid methyl ester Nutrition 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 239000002917 insecticide Substances 0.000 description 3
- 239000004033 plastic Substances 0.000 description 3
- IAGBQBDKOCVGCC-UHFFFAOYSA-N (E)-Ac-7-Tetradecen-1-o Natural products CCCCCCCCC=CCCCCOC(C)=O IAGBQBDKOCVGCC-UHFFFAOYSA-N 0.000 description 2
- IAGBQBDKOCVGCC-KHPPLWFESA-N 5Z-Tetradecenyl acetate Chemical compound CCCCCCCC\C=C/CCCCOC(C)=O IAGBQBDKOCVGCC-KHPPLWFESA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- 241000519878 Anomala rufocuprea Species 0.000 description 2
- 244000068988 Glycine max Species 0.000 description 2
- 235000010469 Glycine max Nutrition 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 230000004071 biological effect Effects 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 239000012634 fragment Substances 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- -1 lithium aluminum hydride Chemical compound 0.000 description 2
- 230000014759 maintenance of location Effects 0.000 description 2
- 238000004949 mass spectrometry Methods 0.000 description 2
- 238000001819 mass spectrum Methods 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- PMOIAJVKYNVHQE-UHFFFAOYSA-N phosphanium;bromide Chemical compound [PH4+].[Br-] PMOIAJVKYNVHQE-UHFFFAOYSA-N 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- ILVXOBCQQYKLDS-UHFFFAOYSA-N pyridine N-oxide Chemical compound [O-][N+]1=CC=CC=C1 ILVXOBCQQYKLDS-UHFFFAOYSA-N 0.000 description 2
- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 2
- 229910000104 sodium hydride Inorganic materials 0.000 description 2
- 239000002689 soil Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- TWADJGWUKGOPFG-UHFFFAOYSA-N 2-methoxy-5-methyl-1,3-diphenylbenzene Chemical compound COC1=C(C=2C=CC=CC=2)C=C(C)C=C1C1=CC=CC=C1 TWADJGWUKGOPFG-UHFFFAOYSA-N 0.000 description 1
- AFGUVBVUFZMJMX-MDZDMXLPSA-N 5-Tetradecenoic acid Chemical compound CCCCCCCC\C=C\CCCC(O)=O AFGUVBVUFZMJMX-MDZDMXLPSA-N 0.000 description 1
- 230000005526 G1 to G0 transition Effects 0.000 description 1
- 244000043261 Hevea brasiliensis Species 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 230000021736 acetylation Effects 0.000 description 1
- 238000006640 acetylation reaction Methods 0.000 description 1
- 239000003463 adsorbent Substances 0.000 description 1
- 239000003708 ampul Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 238000000451 chemical ionisation Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 244000037666 field crops Species 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 239000002035 hexane extract Substances 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000001282 iso-butane Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000007758 mating behavior Effects 0.000 description 1
- CKTWGIPZKUEHIY-BUHFOSPRSA-N methyl (E)-tetradec-2-enoate Chemical compound CCCCCCCCCCC\C=C\C(=O)OC CKTWGIPZKUEHIY-BUHFOSPRSA-N 0.000 description 1
- QCZPJJIXHJSOMY-UHFFFAOYSA-N methyl 2-hydroxypentanoate Chemical compound CCCC(O)C(=O)OC QCZPJJIXHJSOMY-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 229920003052 natural elastomer Polymers 0.000 description 1
- 229920001194 natural rubber Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000012495 reaction gas Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910001961 silver nitrate Inorganic materials 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 229920003051 synthetic elastomer Polymers 0.000 description 1
- 229920001059 synthetic polymer Polymers 0.000 description 1
- 239000005061 synthetic rubber Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000009423 ventilation Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP25520284A JPS61134348A (ja) | 1984-12-03 | 1984-12-03 | ５―テトラデセン酸メチルの製造法 |
| JP18740889A JPH02243606A (ja) | 1984-12-03 | 1989-07-21 | ５―テトラデセン酸メチルを有効成分とする昆虫誘引剤 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP25520284A JPS61134348A (ja) | 1984-12-03 | 1984-12-03 | ５―テトラデセン酸メチルの製造法 |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP18740889A Division JPH02243606A (ja) | 1984-12-03 | 1989-07-21 | ５―テトラデセン酸メチルを有効成分とする昆虫誘引剤 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS61134348A JPS61134348A (ja) | 1986-06-21 |
| JPH0212463B2 true JPH0212463B2 (cs) | 1990-03-20 |
Family
ID=17275437
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP25520284A Granted JPS61134348A (ja) | 1984-12-03 | 1984-12-03 | ５―テトラデセン酸メチルの製造法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS61134348A (cs) |
-
1984
- 1984-12-03 JP JP25520284A patent/JPS61134348A/ja active Granted
Non-Patent Citations (3)
| Title |
|---|
| CHEM.PHYS.LIPIDS=1976 * |
| CHEM.PHYS.LIPIDS=1977 * |
| J.AGR.FOOD CHEM=1970 * |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS61134348A (ja) | 1986-06-21 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EXPY | Cancellation because of completion of term |