GB1435621A - Tetra-deca-9,11-dienyl acetate and sex attractant composi tions thereof for insects - Google Patents
Tetra-deca-9,11-dienyl acetate and sex attractant composi tions thereof for insectsInfo
- Publication number
- GB1435621A GB1435621A GB5108373A GB5108373A GB1435621A GB 1435621 A GB1435621 A GB 1435621A GB 5108373 A GB5108373 A GB 5108373A GB 5108373 A GB5108373 A GB 5108373A GB 1435621 A GB1435621 A GB 1435621A
- Authority
- GB
- United Kingdom
- Prior art keywords
- cis
- isomers
- trans
- bromo
- give
- 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
Links
- 239000000203 mixture Substances 0.000 title abstract 5
- RFEQLTBBKNKGGJ-UHFFFAOYSA-N tetradeca-9,11-dienyl acetate Chemical compound CCC=CC=CCCCCCCCCOC(C)=O RFEQLTBBKNKGGJ-UHFFFAOYSA-N 0.000 title abstract 3
- 241000238631 Hexapoda Species 0.000 title abstract 2
- 239000000877 Sex Attractant Substances 0.000 title abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 5
- 238000000034 method Methods 0.000 abstract 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 abstract 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 3
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 abstract 2
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N Butyraldehyde Chemical compound CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 abstract 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 2
- KDKYADYSIPSCCQ-UHFFFAOYSA-N but-1-yne Chemical compound CCC#C KDKYADYSIPSCCQ-UHFFFAOYSA-N 0.000 abstract 2
- 239000003054 catalyst Substances 0.000 abstract 2
- 238000004817 gas chromatography Methods 0.000 abstract 2
- 238000005984 hydrogenation reaction Methods 0.000 abstract 2
- 238000000926 separation method Methods 0.000 abstract 2
- 125000006527 (C1-C5) alkyl group Chemical group 0.000 abstract 1
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 abstract 1
- MMXRRNUXCHUHOE-UHFFFAOYSA-N 7-bromoheptan-1-ol Chemical compound OCCCCCCCBr MMXRRNUXCHUHOE-UHFFFAOYSA-N 0.000 abstract 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 abstract 1
- GPKLMZVFOHHTDT-UHFFFAOYSA-N BrCCCCCCCCO.C(CCCCCCC)(O)O.C(CCCCCCC(=O)O)(=O)O Chemical compound BrCCCCCCCCO.C(CCCCCCC)(O)O.C(CCCCCCC(=O)O)(=O)O GPKLMZVFOHHTDT-UHFFFAOYSA-N 0.000 abstract 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 abstract 1
- 239000012346 acetyl chloride Substances 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 150000004791 alkyl magnesium halides Chemical class 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- SXCBDZAEHILGLM-UHFFFAOYSA-N heptane-1,7-diol Chemical compound OCCCCCCCO SXCBDZAEHILGLM-UHFFFAOYSA-N 0.000 abstract 1
- 229910052740 iodine Inorganic materials 0.000 abstract 1
- 239000011630 iodine Substances 0.000 abstract 1
- 150000007522 mineralic acids Chemical class 0.000 abstract 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract 1
- JBYXPOFIGCOSSB-UQGDGPGGSA-N rumenic acid Chemical class CCCCCC\C=C/C=C/CCCCCCCC(O)=O JBYXPOFIGCOSSB-UQGDGPGGSA-N 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- 125000004187 tetrahydropyran-2-yl group Chemical group [H]C1([H])OC([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 abstract 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 abstract 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 abstract 1
- HGBOYTHUEUWSSQ-UHFFFAOYSA-N valeric aldehyde Natural products CCCCC=O HGBOYTHUEUWSSQ-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D309/08—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D309/10—Oxygen atoms
- C07D309/12—Oxygen atoms only hydrogen atoms and one oxygen atom directly attached to ring carbon atoms, e.g. tetrahydropyranyl ethers
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/36—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions with formation of hydroxy groups, which may occur via intermediates being derivatives of hydroxy, e.g. O-metal
- C07C29/38—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions with formation of hydroxy groups, which may occur via intermediates being derivatives of hydroxy, e.g. O-metal by reaction with aldehydes or ketones
- C07C29/42—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions with formation of hydroxy groups, which may occur via intermediates being derivatives of hydroxy, e.g. O-metal by reaction with aldehydes or ketones with compounds containing triple carbon-to-carbon bonds, e.g. with metal-alkynes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/28—Preparation of carboxylic acid esters by modifying the hydroxylic moiety of the ester, such modification not being an introduction of an ester group
- C07C67/283—Preparation of carboxylic acid esters by modifying the hydroxylic moiety of the ester, such modification not being an introduction of an ester group by hydrogenation of unsaturated carbon-to-carbon bonds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/28—Preparation of carboxylic acid esters by modifying the hydroxylic moiety of the ester, such modification not being an introduction of an ester group
- C07C67/293—Preparation of carboxylic acid esters by modifying the hydroxylic moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/48—Separation; Purification; Stabilisation; Use of additives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/02—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen
- C07C69/12—Acetic acid esters
- C07C69/14—Acetic acid esters of monohydroxylic compounds
- C07C69/145—Acetic acid esters of monohydroxylic compounds of unsaturated alcohols
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/09—Geometrical isomers
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP5259473A JPS537503B2 (enrdf_load_stackoverflow) | 1973-05-14 | 1973-05-14 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1435621A true GB1435621A (en) | 1976-05-12 |
Family
ID=12919098
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB5108373A Expired GB1435621A (en) | 1973-05-14 | 1973-11-02 | Tetra-deca-9,11-dienyl acetate and sex attractant composi tions thereof for insects |
Country Status (9)
| Country | Link |
|---|---|
| JP (1) | JPS537503B2 (enrdf_load_stackoverflow) |
| CA (1) | CA1024522A (enrdf_load_stackoverflow) |
| CH (2) | CH605594A5 (enrdf_load_stackoverflow) |
| DE (1) | DE2406259B2 (enrdf_load_stackoverflow) |
| EG (1) | EG12459A (enrdf_load_stackoverflow) |
| FR (1) | FR2229678B1 (enrdf_load_stackoverflow) |
| GB (1) | GB1435621A (enrdf_load_stackoverflow) |
| IL (1) | IL43269A (enrdf_load_stackoverflow) |
| NL (1) | NL168494C (enrdf_load_stackoverflow) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2839762A1 (de) * | 1977-09-14 | 1979-03-22 | Montedison Spa | Verfahren zur herstellung aliphatischer verbindungen mit zwei konjugierten cis,cis- oder cis,trans-doppelbindungen |
| CN116267931A (zh) * | 2023-05-12 | 2023-06-23 | 中国农业科学院草原研究所 | 1,4-丁二醇-二甲基丙烯酸酯作为六斑平颜蚜蝇性引诱剂的应用 |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1992009199A1 (en) * | 1990-11-23 | 1992-06-11 | Kansas State University Research Foundation | Method of attracting male hessian flies |
| CZ301579B6 (cs) * | 2005-11-04 | 2010-04-21 | Ústav organické chemie a biochemie, Akademie ved CR | Prostredek pro kontrolu motýla zavíjece Euzophera batangensis a jeho použití |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1387462A (fr) * | 1963-02-08 | 1965-01-29 | Bayer Ag | Procédé de production de diènes conjugués cis, trans |
-
1973
- 1973-05-14 JP JP5259473A patent/JPS537503B2/ja not_active Expired
- 1973-09-19 IL IL43269A patent/IL43269A/en unknown
- 1973-10-12 CA CA183,240A patent/CA1024522A/en not_active Expired
- 1973-10-29 FR FR7338497A patent/FR2229678B1/fr not_active Expired
- 1973-10-31 NL NLAANVRAGE7314949,A patent/NL168494C/xx not_active IP Right Cessation
- 1973-11-02 GB GB5108373A patent/GB1435621A/en not_active Expired
- 1973-12-24 EG EG483/73A patent/EG12459A/xx active
-
1974
- 1974-02-09 DE DE19742406259 patent/DE2406259B2/de active Granted
- 1974-04-17 CH CH83377A patent/CH605594A5/xx not_active IP Right Cessation
- 1974-04-17 CH CH83277A patent/CH605593A5/xx not_active IP Right Cessation
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2839762A1 (de) * | 1977-09-14 | 1979-03-22 | Montedison Spa | Verfahren zur herstellung aliphatischer verbindungen mit zwei konjugierten cis,cis- oder cis,trans-doppelbindungen |
| FR2403327A1 (fr) * | 1977-09-14 | 1979-04-13 | Montedison Spa | Procede de preparation de composes aliphatiques contenant deux doubles liaisons conjuguees |
| CN116267931A (zh) * | 2023-05-12 | 2023-06-23 | 中国农业科学院草原研究所 | 1,4-丁二醇-二甲基丙烯酸酯作为六斑平颜蚜蝇性引诱剂的应用 |
| CN116267931B (zh) * | 2023-05-12 | 2023-07-21 | 中国农业科学院草原研究所 | 1,4-丁二醇-二甲基丙烯酸酯作为六斑平颜蚜蝇性引诱剂的应用 |
Also Published As
| Publication number | Publication date |
|---|---|
| IL43269A (en) | 1976-06-30 |
| DE2406259A1 (de) | 1974-12-05 |
| IL43269A0 (en) | 1973-11-28 |
| FR2229678B1 (enrdf_load_stackoverflow) | 1978-11-17 |
| EG12459A (en) | 1979-12-31 |
| JPS537503B2 (enrdf_load_stackoverflow) | 1978-03-18 |
| NL168494C (nl) | 1982-04-16 |
| CA1024522A (en) | 1978-01-17 |
| CH605594A5 (enrdf_load_stackoverflow) | 1978-09-29 |
| FR2229678A1 (enrdf_load_stackoverflow) | 1974-12-13 |
| NL168494B (nl) | 1981-11-16 |
| JPS504248A (enrdf_load_stackoverflow) | 1975-01-17 |
| CH605593A5 (enrdf_load_stackoverflow) | 1978-09-29 |
| NL7314949A (enrdf_load_stackoverflow) | 1974-11-18 |
| DE2406259B2 (de) | 1976-12-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| PE20 | Patent expired after termination of 20 years |
Effective date: 19931101 |