JPH0586788B2 - - Google Patents

Info

Publication number: JPH0586788B2
Authority: JP; Japan
Prior art keywords: pyran; dihydro; trimethyl; methyl; compound
Prior art date: 1986-02-26
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

Application number

JP3915586A

Other languages

English (en)

Japanese (ja)

Other versions

JPS62198674A (ja

Inventor

Hisashi Kodama

Keiko Mochizuki

Masahiro Kono

Akio Oonishi

Mikio Ono

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Fuji Flavor Co Ltd

Japan Tobacco Inc

Original Assignee

Fuji Flavor Co Ltd

Japan Tobacco Inc

Priority date (The priority date 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 date listed.)

1986-02-26

Filing date

1986-02-26

Publication date

1993-12-14

1986-02-26 Application filed by Fuji Flavor Co Ltd, Japan Tobacco Inc filed Critical Fuji Flavor Co Ltd

1986-02-26 Priority to JP3915586A priority Critical patent/JPS62198674A/ja

1986-03-26 Priority to EP86104205A priority patent/EP0197443B1/en

1986-03-26 Priority to DE8686104205T priority patent/DE3663944D1/de

1986-03-27 Priority to US06/844,598 priority patent/US4782168A/en

1986-03-27 Priority to CA000505262A priority patent/CA1261859A/en

1987-09-02 Publication of JPS62198674A publication Critical patent/JPS62198674A/ja

1993-12-14 Publication of JPH0586788B2 publication Critical patent/JPH0586788B2/ja

Status Granted legal-status Critical Current

Links

GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 claims description 5
101150065749 Churc1 gene Proteins 0.000 claims description 5
102100038239 Protein Churchill Human genes 0.000 claims description 5
UIFJGMGRKBEFOU-UHFFFAOYSA-N 2,3,5-trimethyl-2,3-dihydropyran-4-one Chemical class CC1OC=C(C)C(=O)C1C UIFJGMGRKBEFOU-UHFFFAOYSA-N 0.000 claims description 3
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
OSFBJERFMQCEQY-UHFFFAOYSA-N propylidene Chemical compound [CH]CC OSFBJERFMQCEQY-UHFFFAOYSA-N 0.000 claims description 2
239000004480 active ingredient Substances 0.000 claims 1
150000001875 compounds Chemical class 0.000 description 33
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 20
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
239000000877 Sex Attractant Substances 0.000 description 11
241000254173 Coleoptera Species 0.000 description 10
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
241000238631 Hexapoda Species 0.000 description 9
241000607479 Yersinia pestis Species 0.000 description 9
238000006243 chemical reaction Methods 0.000 description 9
238000004458 analytical method Methods 0.000 description 8
230000000694 effects Effects 0.000 description 8
238000001819 mass spectrum Methods 0.000 description 8
PYOKUURKVVELLB-UHFFFAOYSA-N trimethyl orthoformate Chemical compound COC(OC)OC PYOKUURKVVELLB-UHFFFAOYSA-N 0.000 description 8
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
238000000862 absorption spectrum Methods 0.000 description 7
-1 dimethoxymethyl Chemical group 0.000 description 7
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 6
238000004519 manufacturing process Methods 0.000 description 5
AZAKUWBBRWFVEW-UHFFFAOYSA-N 2,3,5-trimethyl-6-(3-oxopentan-2-yl)-2,3-dihydropyran-4-one Chemical compound CCC(=O)C(C)C1=C(C)C(=O)C(C)C(C)O1 AZAKUWBBRWFVEW-UHFFFAOYSA-N 0.000 description 4
CVQUWLDCFXOXEN-UHFFFAOYSA-N Pyran-4-one Chemical compound O=C1C=COC=C1 CVQUWLDCFXOXEN-UHFFFAOYSA-N 0.000 description 4
239000000853 adhesive Substances 0.000 description 4
230000001070 adhesive effect Effects 0.000 description 4
WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 4
230000007758 mating behavior Effects 0.000 description 4
JNMIXMFEVJHFNY-UHFFFAOYSA-M methyl(triphenyl)phosphanium;iodide Chemical compound [I-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(C)C1=CC=CC=C1 JNMIXMFEVJHFNY-UHFFFAOYSA-M 0.000 description 4
239000000203 mixture Substances 0.000 description 4
239000000575 pesticide Substances 0.000 description 4
239000011541 reaction mixture Substances 0.000 description 4
JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 4
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 3
239000003795 chemical substances by application Substances 0.000 description 3
238000001816 cooling Methods 0.000 description 3
239000003205 fragrance Substances 0.000 description 3
239000011777 magnesium Substances 0.000 description 3
229910052749 magnesium Inorganic materials 0.000 description 3
238000000034 method Methods 0.000 description 3
239000012279 sodium borohydride Substances 0.000 description 3
229910000033 sodium borohydride Inorganic materials 0.000 description 3
238000001228 spectrum Methods 0.000 description 3
238000003756 stirring Methods 0.000 description 3
UEHAJMRYWWCZJG-UHFFFAOYSA-N 6-(1,1-diethoxypropyl)-2,3,5-trimethyl-2,3-dihydropyran-4-one Chemical compound CCOC(CC)(OCC)C1=C(C)C(=O)C(C)C(C)O1 UEHAJMRYWWCZJG-UHFFFAOYSA-N 0.000 description 2
WZBKAFKZRBOKEP-UHFFFAOYSA-N 6-(1-hydroxypropyl)-2,3,5-trimethyl-2,3-dihydropyran-4-one Chemical compound CCC(O)C1=C(C)C(=O)C(C)C(C)O1 WZBKAFKZRBOKEP-UHFFFAOYSA-N 0.000 description 2
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
229910015900 BF3 Inorganic materials 0.000 description 2
239000004743 Polypropylene Substances 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 2
239000012346 acetyl chloride Substances 0.000 description 2
238000009835 boiling Methods 0.000 description 2
GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 description 2
239000003638 chemical reducing agent Substances 0.000 description 2
150000002170 ethers Chemical class 0.000 description 2
SLAFUPJSGFVWPP-UHFFFAOYSA-M ethyl(triphenyl)phosphanium;iodide Chemical compound [I-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(CC)C1=CC=CC=C1 SLAFUPJSGFVWPP-UHFFFAOYSA-M 0.000 description 2
238000002474 experimental method Methods 0.000 description 2
235000013305 food Nutrition 0.000 description 2
FRIJBUGBVQZNTB-UHFFFAOYSA-M magnesium;ethane;bromide Chemical compound [Mg+2].[Br-].[CH2-]C FRIJBUGBVQZNTB-UHFFFAOYSA-M 0.000 description 2
238000004949 mass spectrometry Methods 0.000 description 2
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
229920001155 polypropylene Polymers 0.000 description 2
125000004368 propenyl group Chemical group C(=CC)* 0.000 description 2
239000007921 spray Substances 0.000 description 2
239000000126 substance Substances 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
235000005074 zinc chloride Nutrition 0.000 description 2
239000011592 zinc chloride Substances 0.000 description 2
SEPPVOUBHWNCAW-FNORWQNLSA-N (E)-4-oxonon-2-enal Chemical class CCCCCC(=O)\C=C\C=O SEPPVOUBHWNCAW-FNORWQNLSA-N 0.000 description 1
MEKOFIRRDATTAG-UHFFFAOYSA-N 2,2,5,8-tetramethyl-3,4-dihydrochromen-6-ol Chemical compound C1CC(C)(C)OC2=C1C(C)=C(O)C=C2C MEKOFIRRDATTAG-UHFFFAOYSA-N 0.000 description 1
XNIRJJUVFFMFPY-UHFFFAOYSA-N 2,3,5-trimethyl-6-pent-2-en-2-yl-2,3-dihydropyran-4-one Chemical compound CCC=C(C)C1=C(C)C(=O)C(C)C(C)O1 XNIRJJUVFFMFPY-UHFFFAOYSA-N 0.000 description 1
UDNYCVDWZAFFJR-UHFFFAOYSA-N 2,3,5-trimethyl-6-propanoyl-2,3-dihydropyran-4-one Chemical compound CCC(=O)C1=C(C)C(=O)C(C)C(C)O1 UDNYCVDWZAFFJR-UHFFFAOYSA-N 0.000 description 1
PYNCUTAJKAXSJJ-UHFFFAOYSA-N 2,3,5-trimethylpyran-4-one Chemical class CC1=COC(C)=C(C)C1=O PYNCUTAJKAXSJJ-UHFFFAOYSA-N 0.000 description 1
NEIFEOBTYDRANW-UHFFFAOYSA-N 2-(2,3,5-trimethyl-4-oxo-2,3-dihydropyran-6-yl)propan-2-yl acetate Chemical compound CC1OC(C(C)(C)OC(C)=O)=C(C)C(=O)C1C NEIFEOBTYDRANW-UHFFFAOYSA-N 0.000 description 1
YMEWNPYFMQAHJX-UHFFFAOYSA-N 2-acetylpyran-4-one Chemical compound CC(=O)C1=CC(=O)C=CO1 YMEWNPYFMQAHJX-UHFFFAOYSA-N 0.000 description 1
PKQAHZPFLTXYJB-UHFFFAOYSA-N 2-ethylpyran-4-one Chemical compound CCC1=CC(=O)C=CO1 PKQAHZPFLTXYJB-UHFFFAOYSA-N 0.000 description 1
GILYMBNQNAUVLP-UHFFFAOYSA-N 6-(1,1-dimethoxypropyl)-2,3,5-trimethyl-2,3-dihydropyran-4-one Chemical compound CCC(OC)(OC)C1=C(C)C(=O)C(C)C(C)O1 GILYMBNQNAUVLP-UHFFFAOYSA-N 0.000 description 1
YRFWCFFOAWYPSH-UHFFFAOYSA-N 6-(2-bromopropanoyl)-2,3,5-trimethyl-2,3-dihydropyran-4-one Chemical compound CC(Br)C(=O)C1=C(C)C(=O)C(C)C(C)O1 YRFWCFFOAWYPSH-UHFFFAOYSA-N 0.000 description 1
GJCFOZLMBMFYPM-UHFFFAOYSA-N 6-but-1-enyl-2,3,5-trimethyl-2,3-dihydropyran-4-one Chemical compound CCC=CC1=C(C)C(=O)C(C)C(C)O1 GJCFOZLMBMFYPM-UHFFFAOYSA-N 0.000 description 1
CNHRMHNDQSMEGZ-UHFFFAOYSA-N 6-ethyl-2,3,5-trimethyl-2,3-dihydropyran-4-one Chemical compound CCC1=C(C)C(=O)C(C)C(C)O1 CNHRMHNDQSMEGZ-UHFFFAOYSA-N 0.000 description 1
241000208340 Araliaceae Species 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical class CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 1
235000005035 Panax pseudoginseng ssp. pseudoginseng Nutrition 0.000 description 1
235000003140 Panax quinquefolius Nutrition 0.000 description 1
XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 1
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical class C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 1
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
239000012345 acetylating agent Substances 0.000 description 1
230000000397 acetylating effect Effects 0.000 description 1
238000006640 acetylation reaction Methods 0.000 description 1
125000003172 aldehyde group Chemical group 0.000 description 1
229910052786 argon Inorganic materials 0.000 description 1
239000012298 atmosphere Substances 0.000 description 1
235000015895 biscuits Nutrition 0.000 description 1
235000008429 bread Nutrition 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
238000004891 communication Methods 0.000 description 1
238000012937 correction Methods 0.000 description 1
235000005911 diet Nutrition 0.000 description 1
230000037213 diet Effects 0.000 description 1
235000013601 eggs Nutrition 0.000 description 1
239000000835 fiber Substances 0.000 description 1
WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 1
239000002316 fumigant Substances 0.000 description 1
235000008434 ginseng Nutrition 0.000 description 1
235000008216 herbs Nutrition 0.000 description 1
238000004896 high resolution mass spectrometry Methods 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
239000005457 ice water Substances 0.000 description 1
238000002329 infrared spectrum Methods 0.000 description 1
239000003112 inhibitor Substances 0.000 description 1
239000002917 insecticide Substances 0.000 description 1
239000007788 liquid Substances 0.000 description 1
229940102396 methyl bromide Drugs 0.000 description 1
AZFQCTBZOPUVOW-UHFFFAOYSA-N methyl(triphenyl)phosphanium Chemical class C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(C)C1=CC=CC=C1 AZFQCTBZOPUVOW-UHFFFAOYSA-N 0.000 description 1
238000002156 mixing Methods 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
230000035699 permeability Effects 0.000 description 1
239000003016 pheromone Substances 0.000 description 1
239000000843 powder Substances 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
238000011160 research Methods 0.000 description 1
230000001568 sexual effect Effects 0.000 description 1
238000010898 silica gel chromatography Methods 0.000 description 1
HYEKBBUUXFWKKZ-UHFFFAOYSA-K sodium;zinc;trichloride Chemical compound [Na+].[Cl-].[Cl-].[Cl-].[Zn+2] HYEKBBUUXFWKKZ-UHFFFAOYSA-K 0.000 description 1
238000005507 spraying Methods 0.000 description 1
230000002194 synthesizing effect Effects 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
230000002588 toxic effect Effects 0.000 description 1
GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
239000011701 zinc Substances 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1

Landscapes

Pyrane Compounds (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)

JP3915586A 1985-03-27 1986-02-26 ２，３−ジヒドロ−２，３，５−トリメチル−４ｈ−ピラン−４−オン誘導体およびジンサンシバンムシの性誘引剤 Granted JPS62198674A (ja)

Priority Applications (5)

Application Number	Priority Date	Filing Date	Title
JP3915586A JPS62198674A (ja)	1986-02-26	1986-02-26	２，３−ジヒドロ−２，３，５−トリメチル−４ｈ−ピラン−４−オン誘導体およびジンサンシバンムシの性誘引剤
EP86104205A EP0197443B1 (en)	1985-03-27	1986-03-26	2,3-dihydro-2,3,5-trimethyl-4h-pyran-4-one, derivative and sex attractant for drugstore beetles
DE8686104205T DE3663944D1 (en)	1985-03-27	1986-03-26	2,3-dihydro-2,3,5-trimethyl-4h-pyran-4-one, derivative and sex attractant for drugstore beetles
US06/844,598 US4782168A (en)	1985-03-27	1986-03-27	2,3-dihydro-2,3,5-trimethyl-4H-pyran-4-one derivative and sex attractant for drugstore beetles
CA000505262A CA1261859A (en)	1985-03-27	1986-03-27	2,3-dihydro-2,3,5-trimethyl-4h-pyran-4-one derivative and sex attractant for drugstore beetles

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP3915586A JPS62198674A (ja)	1986-02-26	1986-02-26	２，３−ジヒドロ−２，３，５−トリメチル−４ｈ−ピラン−４−オン誘導体およびジンサンシバンムシの性誘引剤

Publications (2)

Publication Number	Publication Date
JPS62198674A JPS62198674A (ja)	1987-09-02
JPH0586788B2 true JPH0586788B2 (2)	1993-12-14

Family

ID=12545217

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP3915586A Granted JPS62198674A (ja)	1985-03-27	1986-02-26	２，３−ジヒドロ−２，３，５−トリメチル−４ｈ−ピラン−４−オン誘導体およびジンサンシバンムシの性誘引剤

Country Status (1)

Country	Link
JP (1)	JPS62198674A (2)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JP4920290B2 (ja) *	2006-04-18	2012-04-18	富士フレーバー株式会社	２，３−ジヒドロ−２，３，５−トリメチル−６−（１−メチル−２−ブテニル）−４−ｈ−ピラン−４−オンの製造方法およびそれに用いる中間体
JP4941741B2 (ja) *	2007-06-04	2012-05-30	住友電装株式会社	コネクタ
JP4941740B2 (ja) *	2007-06-04	2012-05-30	住友電装株式会社	コネクタ

1986
- 1986-02-26 JP JP3915586A patent/JPS62198674A/ja active Granted

Also Published As

Publication number	Publication date
JPS62198674A (ja)	1987-09-02

Legal Events

Date	Code	Title	Description
2004-11-24	R250	Receipt of annual fees	Free format text: JAPANESE INTERMEDIATE CODE: R250
2005-11-22	R250	Receipt of annual fees	Free format text: JAPANESE INTERMEDIATE CODE: R250
2006-02-26	EXPY	Cancellation because of completion of term

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JP3279818B2 (ja)	2002-04-30	殺虫・殺ダニ剤
KR19990067206A (ko)	1999-08-16	화이트플라이 구제용 화합물
RU2154382C2 (ru)	2000-08-20	Производные нафтохинона, экстракт растительного материала, их использование, фунгицидная, и/или акарицидная, и/или инсектицидная композиция
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JP2823595B2 (ja)	1998-11-11	２，２―ジメチルシクロプロパンカルボン酸のエステル
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