IL90008A - Mediterranean fly-pulling preparations containing esters of 5-iodo-2-methyl-cyclohexane-carboxylic acid esters and methods of use - Google Patents
Mediterranean fly-pulling preparations containing esters of 5-iodo-2-methyl-cyclohexane-carboxylic acid esters and methods of useInfo
- Publication number
- IL90008A IL90008A IL9000889A IL9000889A IL90008A IL 90008 A IL90008 A IL 90008A IL 9000889 A IL9000889 A IL 9000889A IL 9000889 A IL9000889 A IL 9000889A IL 90008 A IL90008 A IL 90008A
- Authority
- IL
- Israel
- Prior art keywords
- composition
- trifluoroethyl
- iodo
- fruit fly
- methyl
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims description 73
- 241000255579 Ceratitis capitata Species 0.000 title claims description 34
- 239000005667 attractant Substances 0.000 title claims description 24
- 230000031902 chemoattractant activity Effects 0.000 title claims description 15
- 238000000034 method Methods 0.000 title claims description 13
- SMZPBBOXXYYADS-UHFFFAOYSA-N 5-iodo-2-methylcyclohexane-1-carboxylic acid Chemical class CC1CCC(I)CC1C(O)=O SMZPBBOXXYYADS-UHFFFAOYSA-N 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 20
- 125000002346 iodo group Chemical group I* 0.000 claims description 20
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 18
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 16
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 claims description 16
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 9
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 9
- 239000003795 chemical substances by application Substances 0.000 claims description 7
- 239000002917 insecticide Substances 0.000 claims description 3
- 150000002148 esters Chemical class 0.000 description 29
- APMORJJNVZMVQK-UHFFFAOYSA-N tert-butyl 4-chloro-2-methylcyclohexane-1-carboxylate Chemical compound CC1CC(Cl)CCC1C(=O)OC(C)(C)C APMORJJNVZMVQK-UHFFFAOYSA-N 0.000 description 23
- 238000012360 testing method Methods 0.000 description 12
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- 239000002253 acid Substances 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 125000004494 ethyl ester group Chemical group 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 5
- 238000005698 Diels-Alder reaction Methods 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- GKIRPKYJQBWNGO-OCEACIFDSA-N clomifene Chemical group C1=CC(OCCN(CC)CC)=CC=C1C(\C=1C=CC=CC=1)=C(\Cl)C1=CC=CC=C1 GKIRPKYJQBWNGO-OCEACIFDSA-N 0.000 description 3
- 230000002085 persistent effect Effects 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- UTEIUSUWIZICDO-RNFRBKRXSA-N (1r,6r)-6-methylcyclohex-3-ene-1-carboxylic acid Chemical compound C[C@@H]1CC=CC[C@H]1C(O)=O UTEIUSUWIZICDO-RNFRBKRXSA-N 0.000 description 2
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 2
- 235000018330 Macadamia integrifolia Nutrition 0.000 description 2
- 240000000912 Macadamia tetraphylla Species 0.000 description 2
- 235000003800 Macadamia tetraphylla Nutrition 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 241000607479 Yersinia pestis Species 0.000 description 2
- ZZZRZSOTRLRALD-UHFFFAOYSA-N butan-2-yl 4-chloro-2-methylcyclohexane-1-carboxylate;butan-2-yl 5-chloro-2-methylcyclohexane-1-carboxylate Chemical compound CCC(C)OC(=O)C1CCC(Cl)CC1C.CCC(C)OC(=O)C1CC(Cl)CCC1C ZZZRZSOTRLRALD-UHFFFAOYSA-N 0.000 description 2
- AJKDXAOKNSFWAA-UHFFFAOYSA-N butan-2-yl 6-methylcyclohex-3-ene-1-carboxylate Chemical compound CCC(C)OC(=O)C1CC=CCC1C AJKDXAOKNSFWAA-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 238000004508 fractional distillation Methods 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 229910000043 hydrogen iodide Inorganic materials 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 239000002420 orchard Substances 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 230000002688 persistence Effects 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000012266 salt solution Substances 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- 241000506680 Haemulon melanurum Species 0.000 description 1
- 241000238631 Hexapoda Species 0.000 description 1
- 206010061217 Infestation Diseases 0.000 description 1
- PHSPJQZRQAJPPF-UHFFFAOYSA-N N-alpha-Methylhistamine Chemical compound CNCCC1=CN=CN1 PHSPJQZRQAJPPF-UHFFFAOYSA-N 0.000 description 1
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
- 239000002250 absorbent Substances 0.000 description 1
- 230000002745 absorbent Effects 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 238000000540 analysis of variance Methods 0.000 description 1
- 238000004166 bioassay Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 230000003559 chemosterilizing effect Effects 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- ZQWPRMPSCMSAJU-UHFFFAOYSA-N cyclohexanecarboxylic acid methyl ester Natural products COC(=O)C1CCCCC1 ZQWPRMPSCMSAJU-UHFFFAOYSA-N 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 239000002274 desiccant Substances 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 230000002140 halogenating effect Effects 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 235000014571 nuts Nutrition 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000002516 radical scavenger Substances 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000003206 sterilizing agent Substances 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- -1 that is Substances 0.000 description 1
- 238000011282 treatment Methods 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C61/00—Compounds having carboxyl groups bound to carbon atoms of rings other than six-membered aromatic rings
- C07C61/15—Saturated compounds containing halogen
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing carboxylic groups or thio analogues thereof, directly attached by the carbon atom to a cycloaliphatic ring; Derivatives thereof
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Dentistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Plant Pathology (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (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 |
|---|---|---|---|
| US07/186,990 US4891217A (en) | 1987-04-27 | 1988-04-27 | Persistant attractants for the mediterranean fruit fly, the method of preparation and method of use |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL90008A0 IL90008A0 (en) | 1989-12-15 |
| IL90008A true IL90008A (en) | 1994-10-21 |
Family
ID=22687160
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL9000889A IL90008A (en) | 1988-04-27 | 1989-04-18 | Mediterranean fly-pulling preparations containing esters of 5-iodo-2-methyl-cyclohexane-carboxylic acid esters and methods of use |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US4891217A (ja) |
| EP (1) | EP0340971B1 (ja) |
| JP (1) | JPH06681B2 (ja) |
| AU (1) | AU612846B2 (ja) |
| BR (1) | BR8907401A (ja) |
| CA (1) | CA1317219C (ja) |
| ES (1) | ES2061985T3 (ja) |
| IL (1) | IL90008A (ja) |
| PT (1) | PT90367B (ja) |
| WO (1) | WO1989010055A1 (ja) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5728394A (en) * | 1994-12-12 | 1998-03-17 | Photodye International, Inc. | Pesticide composition and method for controlling the oriental fruit fly |
| US6375943B1 (en) | 2000-01-14 | 2002-04-23 | The United States Of America As Represented By The Secretary Of Agriculture | Attractant for the mediterranean fruit fly, the method of preparation and method of use |
| DE102005015446A1 (de) * | 2005-04-05 | 2006-10-12 | Merck Patent Gmbh | Synergisten zur Verstärkung der Wirkung von Repellentien |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3016329A (en) * | 1959-08-06 | 1962-01-09 | Beroza Morton | Attractants for the male mediterranean fruit fly |
| US4152422A (en) * | 1978-02-03 | 1979-05-01 | The United States Of America As Represented By The Secretary Of Agriculture | Attractant for male Mediterranean fruit fly |
| US4764366A (en) * | 1987-04-27 | 1988-08-16 | The United States Of America As Represented By The Secretary Of Agriculture | Persistent attractants for the mediteranean fruit fly, the method of preparation and method of use |
-
1988
- 1988-04-27 US US07/186,990 patent/US4891217A/en not_active Expired - Lifetime
-
1989
- 1989-04-14 BR BR898907401A patent/BR8907401A/pt not_active Application Discontinuation
- 1989-04-14 AU AU35783/89A patent/AU612846B2/en not_active Ceased
- 1989-04-14 JP JP1505831A patent/JPH06681B2/ja not_active Expired - Lifetime
- 1989-04-14 WO PCT/US1989/001501 patent/WO1989010055A1/en not_active Ceased
- 1989-04-18 IL IL9000889A patent/IL90008A/en not_active IP Right Cessation
- 1989-04-21 CA CA000597424A patent/CA1317219C/en not_active Expired - Fee Related
- 1989-04-26 PT PT90367A patent/PT90367B/pt not_active IP Right Cessation
- 1989-04-27 ES ES89304244T patent/ES2061985T3/es not_active Expired - Lifetime
- 1989-04-27 EP EP89304244A patent/EP0340971B1/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| EP0340971B1 (en) | 1994-01-19 |
| IL90008A0 (en) | 1989-12-15 |
| WO1989010055A1 (en) | 1989-11-02 |
| JPH03502581A (ja) | 1991-06-13 |
| CA1317219C (en) | 1993-05-04 |
| ES2061985T3 (es) | 1994-12-16 |
| EP0340971A3 (en) | 1991-09-11 |
| BR8907401A (pt) | 1991-04-23 |
| EP0340971A2 (en) | 1989-11-08 |
| PT90367B (pt) | 1991-10-31 |
| AU612846B2 (en) | 1991-07-18 |
| JPH06681B2 (ja) | 1994-01-05 |
| US4891217A (en) | 1990-01-02 |
| AU3578389A (en) | 1989-11-24 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| RH | Patent void |