IL43269A - Preparation of tetradeca-9,11-dienyl acetate and compositions containing it for controlling insects - Google Patents
Preparation of tetradeca-9,11-dienyl acetate and compositions containing it for controlling insectsInfo
- Publication number
- IL43269A IL43269A IL43269A IL4326973A IL43269A IL 43269 A IL43269 A IL 43269A IL 43269 A IL43269 A IL 43269A IL 4326973 A IL4326973 A IL 4326973A IL 43269 A IL43269 A IL 43269A
- Authority
- IL
- Israel
- Prior art keywords
- tetradeca
- acetate
- cis
- trans
- dienyl
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims 18
- 241000238631 Hexapoda Species 0.000 title claims 9
- RFEQLTBBKNKGGJ-UHFFFAOYSA-N tetradeca-9,11-dienyl acetate Chemical compound CCC=CC=CCCCCCCCCOC(C)=O RFEQLTBBKNKGGJ-UHFFFAOYSA-N 0.000 title claims 4
- 238000000034 method Methods 0.000 claims 38
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims 15
- 241000894007 species Species 0.000 claims 11
- 230000021736 acetylation Effects 0.000 claims 8
- 238000006640 acetylation reaction Methods 0.000 claims 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 6
- 239000003054 catalyst Substances 0.000 claims 6
- 150000001875 compounds Chemical class 0.000 claims 6
- 239000000877 Sex Attractant Substances 0.000 claims 5
- 241000256250 Spodoptera littoralis Species 0.000 claims 5
- 241000985245 Spodoptera litura Species 0.000 claims 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims 4
- 150000007522 mineralic acids Chemical class 0.000 claims 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims 3
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims 3
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 claims 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 2
- 101150065749 Churc1 gene Proteins 0.000 claims 2
- 241000012186 Litura Species 0.000 claims 2
- 102100038239 Protein Churchill Human genes 0.000 claims 2
- 241000256248 Spodoptera Species 0.000 claims 2
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 claims 2
- 239000012346 acetyl chloride Substances 0.000 claims 2
- 125000000217 alkyl group Chemical group 0.000 claims 2
- 125000005843 halogen group Chemical group 0.000 claims 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- 230000007062 hydrolysis Effects 0.000 claims 2
- 238000006460 hydrolysis reaction Methods 0.000 claims 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 2
- ZZGJZGSVLNSDPG-UHFFFAOYSA-N tetradeca-9,12-dienyl acetate Chemical compound CC=CCC=CCCCCCCCCOC(C)=O ZZGJZGSVLNSDPG-UHFFFAOYSA-N 0.000 claims 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims 1
- AHPPBLXNBUAWCQ-VOTSOKGWSA-N [(11e)-tetradeca-11,13-dien-4-yl] acetate Chemical compound CCCC(OC(C)=O)CCCCCC\C=C\C=C AHPPBLXNBUAWCQ-VOTSOKGWSA-N 0.000 claims 1
- UCTLHLZWKJIXJI-LXIBVNSESA-N [(3s,8r,9s,10r,13s,14s)-17-chloro-16-formyl-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15-decahydro-1h-cyclopenta[a]phenanthren-3-yl] acetate Chemical compound C([C@@H]12)C[C@]3(C)C(Cl)=C(C=O)C[C@H]3[C@@H]1CC=C1[C@]2(C)CC[C@H](OC(=O)C)C1 UCTLHLZWKJIXJI-LXIBVNSESA-N 0.000 claims 1
- 150000001242 acetic acid derivatives Chemical class 0.000 claims 1
- 150000004791 alkyl magnesium halides Chemical class 0.000 claims 1
- 150000008064 anhydrides Chemical class 0.000 claims 1
- 150000004820 halides Chemical class 0.000 claims 1
- 238000005984 hydrogenation reaction Methods 0.000 claims 1
- 238000011835 investigation Methods 0.000 claims 1
- 229910052740 iodine Inorganic materials 0.000 claims 1
- 239000011630 iodine Substances 0.000 claims 1
- FRIJBUGBVQZNTB-UHFFFAOYSA-M magnesium;ethane;bromide Chemical group [Mg+2].[Br-].[CH2-]C FRIJBUGBVQZNTB-UHFFFAOYSA-M 0.000 claims 1
- YYROPELSRYBVMQ-UHFFFAOYSA-N p-toluenesulfonyl chloride Substances CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 claims 1
- 230000002195 synergetic effect Effects 0.000 claims 1
- MGGFVUDHXXJTRI-UHFFFAOYSA-N tetradec-11-en-9-ynyl acetate Chemical compound CCC=CC#CCCCCCCCCOC(C)=O MGGFVUDHXXJTRI-UHFFFAOYSA-N 0.000 claims 1
- -1 trans-9-tetradecen-11-ynyl acetate Chemical compound 0.000 claims 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims 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 (2)
| Publication Number | Publication Date |
|---|---|
| IL43269A0 IL43269A0 (en) | 1973-11-28 |
| IL43269A true IL43269A (en) | 1976-06-30 |
Family
ID=12919098
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL43269A IL43269A (en) | 1973-05-14 | 1973-09-19 | Preparation of tetradeca-9,11-dienyl acetate and compositions containing it for controlling 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) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1092258B (it) * | 1977-09-14 | 1985-07-06 | Montedison Spa | Processo per preparare composti alifatici contenenti due doppi legami coniugati ci-cis e cis-trans e sua applicazione in una sintesi del cis,trans-9,11-tetradecadienil-acetato |
| 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 |
| 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 |
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
Also Published As
| Publication number | Publication date |
|---|---|
| DE2406259A1 (de) | 1974-12-05 |
| GB1435621A (en) | 1976-05-12 |
| 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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