IL27756A - Preparation and use of polychloro ketoalkenoic acids and their corresponding lactones - Google Patents
Preparation and use of polychloro ketoalkenoic acids and their corresponding lactonesInfo
- Publication number
- IL27756A IL27756A IL27756A IL2775667A IL27756A IL 27756 A IL27756 A IL 27756A IL 27756 A IL27756 A IL 27756A IL 2775667 A IL2775667 A IL 2775667A IL 27756 A IL27756 A IL 27756A
- Authority
- IL
- Israel
- Prior art keywords
- keto
- acid
- lactone
- reaction
- temperature
- Prior art date
Links
- 239000002253 acid Substances 0.000 title claims description 23
- 150000002596 lactones Chemical class 0.000 title claims description 14
- 150000007513 acids Chemical class 0.000 title claims description 10
- 238000002360 preparation method Methods 0.000 title description 3
- JOOXCMJARBKPKM-UHFFFAOYSA-N 4-oxopentanoic acid Chemical compound CC(=O)CCC(O)=O JOOXCMJARBKPKM-UHFFFAOYSA-N 0.000 claims description 40
- 150000001875 compounds Chemical class 0.000 claims description 23
- 229940040102 levulinic acid Drugs 0.000 claims description 20
- 238000000034 method Methods 0.000 claims description 20
- RRLHZVASKJLNFJ-UHFFFAOYSA-N 2,3,5,5,5-pentachloro-4-oxopent-2-enoic acid Chemical compound OC(=O)C(Cl)=C(Cl)C(=O)C(Cl)(Cl)Cl RRLHZVASKJLNFJ-UHFFFAOYSA-N 0.000 claims description 13
- 238000006243 chemical reaction Methods 0.000 claims description 12
- 230000002363 herbicidal effect Effects 0.000 claims description 12
- -1 phenyl ester Chemical class 0.000 claims description 11
- 150000002148 esters Chemical class 0.000 claims description 9
- 239000000203 mixture Substances 0.000 claims description 9
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 8
- 239000004009 herbicide Substances 0.000 claims description 8
- 150000008064 anhydrides Chemical class 0.000 claims description 7
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 238000006356 dehydrogenation reaction Methods 0.000 claims description 5
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 4
- 150000001266 acyl halides Chemical class 0.000 claims description 4
- 150000001408 amides Chemical class 0.000 claims description 4
- 230000003115 biocidal effect Effects 0.000 claims description 4
- 239000007858 starting material Substances 0.000 claims description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
- 239000000417 fungicide Substances 0.000 claims description 3
- 230000035484 reaction time Effects 0.000 claims description 3
- MGAXYKDBRBNWKT-UHFFFAOYSA-N (5-oxooxolan-2-yl)methyl 4-methylbenzenesulfonate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)OCC1OC(=O)CC1 MGAXYKDBRBNWKT-UHFFFAOYSA-N 0.000 claims description 2
- 230000000855 fungicidal effect Effects 0.000 claims description 2
- 125000000468 ketone group Chemical group 0.000 claims description 2
- 239000000575 pesticide Substances 0.000 claims description 2
- 150000001263 acyl chlorides Chemical class 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 239000000460 chlorine Substances 0.000 description 15
- 229910052801 chlorine Inorganic materials 0.000 description 15
- 230000012010 growth Effects 0.000 description 14
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 13
- 238000005660 chlorination reaction Methods 0.000 description 12
- 229920000742 Cotton Polymers 0.000 description 8
- 244000299507 Gossypium hirsutum Species 0.000 description 8
- 241000196324 Embryophyta Species 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 230000000749 insecticidal effect Effects 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 240000008067 Cucumis sativus Species 0.000 description 5
- 235000007688 Lycopersicon esculentum Nutrition 0.000 description 5
- 244000046052 Phaseolus vulgaris Species 0.000 description 5
- 241000220259 Raphanus Species 0.000 description 5
- 235000006140 Raphanus sativus var sativus Nutrition 0.000 description 5
- 240000003768 Solanum lycopersicum Species 0.000 description 5
- 240000008042 Zea mays Species 0.000 description 5
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 5
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 5
- 235000005822 corn Nutrition 0.000 description 5
- 235000010799 Cucumis sativus var sativus Nutrition 0.000 description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
- 230000002053 acidogenic effect Effects 0.000 description 4
- 238000010790 dilution Methods 0.000 description 4
- 239000012895 dilution Substances 0.000 description 4
- 235000016068 Berberis vulgaris Nutrition 0.000 description 3
- 241000335053 Beta vulgaris Species 0.000 description 3
- 102100028524 Lysosomal protective protein Human genes 0.000 description 3
- 101710162021 Lysosomal protective protein Proteins 0.000 description 3
- 241000209140 Triticum Species 0.000 description 3
- 235000021307 Triticum Nutrition 0.000 description 3
- 125000002252 acyl group Chemical group 0.000 description 3
- 230000002421 anti-septic effect Effects 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 239000002917 insecticide Substances 0.000 description 3
- 150000004715 keto acids Chemical class 0.000 description 3
- 235000021332 kidney beans Nutrition 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- GMEONFUTDYJSNV-UHFFFAOYSA-N Ethyl levulinate Chemical compound CCOC(=O)CCC(C)=O GMEONFUTDYJSNV-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 229930194542 Keto Natural products 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- 230000000844 anti-bacterial effect Effects 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- BIWJNBZANLAXMG-YQELWRJZSA-N chloordaan Chemical compound ClC1=C(Cl)[C@@]2(Cl)C3CC(Cl)C(Cl)C3[C@]1(Cl)C2(Cl)Cl BIWJNBZANLAXMG-YQELWRJZSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 230000035613 defoliation Effects 0.000 description 2
- 230000002070 germicidal effect Effects 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 230000000979 retarding effect Effects 0.000 description 2
- 230000001988 toxicity Effects 0.000 description 2
- 231100000419 toxicity Toxicity 0.000 description 2
- KWOHONYYAXGTMN-UHFFFAOYSA-N 2,2-dimethyl-4-oxopentanoic acid Chemical compound CC(=O)CC(C)(C)C(O)=O KWOHONYYAXGTMN-UHFFFAOYSA-N 0.000 description 1
- QHYCCVUJZIPAMP-UHFFFAOYSA-N 2,3,5,5-tetrachloro-4-oxopent-2-enoic acid Chemical compound OC(=O)C(Cl)=C(Cl)C(=O)C(Cl)Cl QHYCCVUJZIPAMP-UHFFFAOYSA-N 0.000 description 1
- 241000238876 Acari Species 0.000 description 1
- 241000228212 Aspergillus Species 0.000 description 1
- 235000007319 Avena orientalis Nutrition 0.000 description 1
- 244000075850 Avena orientalis Species 0.000 description 1
- 241000254173 Coleoptera Species 0.000 description 1
- 235000009849 Cucumis sativus Nutrition 0.000 description 1
- 241000255581 Drosophila <fruit fly, genus> Species 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 241000233866 Fungi Species 0.000 description 1
- 244000068988 Glycine max Species 0.000 description 1
- 235000010469 Glycine max Nutrition 0.000 description 1
- 241000238631 Hexapoda Species 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 235000004431 Linum usitatissimum Nutrition 0.000 description 1
- 240000006240 Linum usitatissimum Species 0.000 description 1
- 241000257159 Musca domestica Species 0.000 description 1
- 241000244206 Nematoda Species 0.000 description 1
- 241000255588 Tephritidae Species 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 238000005903 acid hydrolysis reaction Methods 0.000 description 1
- YIYBQIKDCADOSF-UHFFFAOYSA-N alpha-Butylen-alpha-carbonsaeure Natural products CCC=CC(O)=O YIYBQIKDCADOSF-UHFFFAOYSA-N 0.000 description 1
- 239000003899 bactericide agent Substances 0.000 description 1
- BGLUXFNVVSVEET-UHFFFAOYSA-N beta-angelica lactone Chemical class CC1OC(=O)C=C1 BGLUXFNVVSVEET-UHFFFAOYSA-N 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000012612 commercial material Substances 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 239000002837 defoliant Substances 0.000 description 1
- 150000005690 diesters Chemical class 0.000 description 1
- 230000003292 diminished effect Effects 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 230000035784 germination Effects 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000002440 hydroxy compounds Chemical class 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 230000002147 killing effect Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 235000012054 meals Nutrition 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 230000008635 plant growth Effects 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- YIYBQIKDCADOSF-ONEGZZNKSA-N trans-pent-2-enoic acid Chemical compound CC\C=C\C(O)=O YIYBQIKDCADOSF-ONEGZZNKSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three 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
- C07D307/58—One oxygen atom, e.g. butenolide
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
- C07C51/363—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by introduction of halogen; by substitution of halogen atoms by other halogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (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 |
|---|---|---|---|
| US54109666A | 1966-04-08 | 1966-04-08 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| IL27756A true IL27756A (en) | 1972-08-30 |
Family
ID=24158160
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL27756A IL27756A (en) | 1966-04-08 | 1967-04-07 | Preparation and use of polychloro ketoalkenoic acids and their corresponding lactones |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US3577546A (2) |
| BE (1) | BE696803A (2) |
| DE (1) | DE1618051A1 (2) |
| DK (1) | DK123019B (2) |
| ES (1) | ES338958A1 (2) |
| FR (1) | FR2558M (2) |
| GB (1) | GB1185200A (2) |
| IL (1) | IL27756A (2) |
| NL (1) | NL6704989A (2) |
| SE (1) | SE352620B (2) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN117720633B (zh) * | 2024-02-08 | 2024-05-14 | 鄂尔多斯市中心医院（内蒙古自治区超声影像研究所） | 一种蜱的镇痛蛋白及其编码基因在镇痛中的应用 |
-
1963
- 1963-04-26 FR FR932811A patent/FR2558M/fr active Active
-
1966
- 1966-04-08 US US541096A patent/US3577546A/en not_active Expired - Lifetime
-
1967
- 1967-04-06 DE DE19671618051 patent/DE1618051A1/de active Pending
- 1967-04-06 ES ES338958A patent/ES338958A1/es not_active Expired
- 1967-04-07 BE BE696803D patent/BE696803A/xx unknown
- 1967-04-07 IL IL27756A patent/IL27756A/en unknown
- 1967-04-07 DK DK196067AA patent/DK123019B/da unknown
- 1967-04-07 GB GB05998/67A patent/GB1185200A/en not_active Expired
- 1967-04-07 SE SE04859/67A patent/SE352620B/xx unknown
- 1967-04-07 NL NL6704989A patent/NL6704989A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| BE696803A (2) | 1967-10-09 |
| NL6704989A (2) | 1967-10-09 |
| US3577546A (en) | 1971-05-04 |
| SE352620B (2) | 1973-01-08 |
| FR2558M (fr) | 1964-05-25 |
| ES338958A1 (es) | 1968-09-01 |
| DK123019B (da) | 1972-05-08 |
| GB1185200A (en) | 1970-03-25 |
| DE1618051A1 (de) | 1970-10-22 |
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