CH564007A5 - - Google Patents
Info
- Publication number
- CH564007A5 CH564007A5 CH1918971A CH1918971A CH564007A5 CH 564007 A5 CH564007 A5 CH 564007A5 CH 1918971 A CH1918971 A CH 1918971A CH 1918971 A CH1918971 A CH 1918971A CH 564007 A5 CH564007 A5 CH 564007A5
- Authority
- CH
- Switzerland
- Prior art keywords
- benzene
- larvae
- methylenedioxy
- ethyl
- mixture
- Prior art date
Links
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 37
- -1 4-ethyl-8-methyldecyl Chemical group 0.000 claims description 27
- 150000001875 compounds Chemical class 0.000 claims description 27
- 238000000034 method Methods 0.000 claims description 27
- 239000000203 mixture Substances 0.000 claims description 20
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 14
- LUSZGTFNYDARNI-UHFFFAOYSA-N Sesamol Chemical compound OC1=CC=C2OCOC2=C1 LUSZGTFNYDARNI-UHFFFAOYSA-N 0.000 claims description 14
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 14
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 11
- 241000238631 Hexapoda Species 0.000 claims description 11
- 239000002904 solvent Substances 0.000 claims description 11
- 238000002474 experimental method Methods 0.000 claims description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 9
- 239000003795 chemical substances by application Substances 0.000 claims description 9
- 241000238421 Arthropoda Species 0.000 claims description 8
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 claims description 8
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 claims description 8
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 claims description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 8
- 230000012010 growth Effects 0.000 claims description 6
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 claims description 6
- 239000011541 reaction mixture Substances 0.000 claims description 5
- OCCHAUQOGMSORW-UHFFFAOYSA-N 5-(4,8-dimethyldecoxy)-1,3-benzodioxole Chemical compound CCC(C)CCCC(C)CCCOC1=CC=C2OCOC2=C1 OCCHAUQOGMSORW-UHFFFAOYSA-N 0.000 claims description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 claims description 4
- 150000001350 alkyl halides Chemical class 0.000 claims description 4
- 238000009835 boiling Methods 0.000 claims description 4
- 150000001793 charged compounds Chemical class 0.000 claims description 4
- 238000004440 column chromatography Methods 0.000 claims description 4
- 230000001419 dependent effect Effects 0.000 claims description 4
- 239000012259 ether extract Substances 0.000 claims description 4
- 230000001418 larval effect Effects 0.000 claims description 4
- 238000001819 mass spectrum Methods 0.000 claims description 4
- 230000029052 metamorphosis Effects 0.000 claims description 4
- 238000001228 spectrum Methods 0.000 claims description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
- 229910052794 bromium Inorganic materials 0.000 claims description 3
- 239000000460 chlorine Substances 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- FTNJQNQLEGKTGD-UHFFFAOYSA-N 1,3-benzodioxole Chemical compound C1=CC=C2OCOC2=C1 FTNJQNQLEGKTGD-UHFFFAOYSA-N 0.000 claims description 2
- BFPQIDVNBMPFOW-UHFFFAOYSA-N 1-bromo-4,8-dimethyldecane Chemical compound CC(CCCBr)CCCC(CC)C BFPQIDVNBMPFOW-UHFFFAOYSA-N 0.000 claims description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 2
- OSDJVDOQMMHJPA-UHFFFAOYSA-N C(C)C(CCCOC1=CC2=C(C=C1)OCO2)CCCC(CC)C Chemical compound C(C)C(CCCOC1=CC2=C(C=C1)OCO2)CCCC(CC)C OSDJVDOQMMHJPA-UHFFFAOYSA-N 0.000 claims description 2
- JKNAPGTZQSJRBS-UHFFFAOYSA-N CC(CCCOC1=CC2=C(C=C1)OCO2)CCCCCC Chemical compound CC(CCCOC1=CC2=C(C=C1)OCO2)CCCCCC JKNAPGTZQSJRBS-UHFFFAOYSA-N 0.000 claims description 2
- 241000254109 Tenebrio molitor Species 0.000 claims description 2
- 239000012876 carrier material Substances 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 230000018109 developmental process Effects 0.000 claims description 2
- 238000004821 distillation Methods 0.000 claims description 2
- 235000013601 eggs Nutrition 0.000 claims description 2
- 238000001704 evaporation Methods 0.000 claims description 2
- 230000008020 evaporation Effects 0.000 claims description 2
- 239000000284 extract Substances 0.000 claims description 2
- 238000000605 extraction Methods 0.000 claims description 2
- 230000004720 fertilization Effects 0.000 claims description 2
- 230000007773 growth pattern Effects 0.000 claims description 2
- 230000010354 integration Effects 0.000 claims description 2
- 239000011630 iodine Chemical group 0.000 claims description 2
- 229910052740 iodine Chemical group 0.000 claims description 2
- 230000009571 larval growth Effects 0.000 claims description 2
- HCWCAKKEBCNQJP-UHFFFAOYSA-N magnesium orthosilicate Chemical class [Mg+2].[Mg+2].[O-][Si]([O-])([O-])[O-] HCWCAKKEBCNQJP-UHFFFAOYSA-N 0.000 claims description 2
- 239000012299 nitrogen atmosphere Substances 0.000 claims description 2
- 239000000725 suspension Substances 0.000 claims description 2
- 239000000376 reactant Substances 0.000 description 7
- 239000002585 base Substances 0.000 description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
- 239000012429 reaction media Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 241000238814 Orthoptera Species 0.000 description 2
- 230000000366 juvenile effect Effects 0.000 description 2
- 229930014550 juvenile hormone Natural products 0.000 description 2
- 239000002949 juvenile hormone Substances 0.000 description 2
- 150000003633 juvenile hormone derivatives Chemical class 0.000 description 2
- 229930191400 juvenile hormones Natural products 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 230000035800 maturation Effects 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 230000001105 regulatory effect Effects 0.000 description 2
- 241000894007 species Species 0.000 description 2
- 241000255789 Bombyx mori Species 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- 241000257159 Musca domestica Species 0.000 description 1
- 241000254105 Tenebrio Species 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 238000009395 breeding Methods 0.000 description 1
- 230000001488 breeding effect Effects 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 230000035943 smell Effects 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
-
- 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
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
- A01N43/24—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms
- A01N43/26—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms five-membered rings
- A01N43/28—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms five-membered rings with two hetero atoms in positions 1,3
- A01N43/30—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms five-membered rings with two hetero atoms in positions 1,3 with two oxygen atoms in positions 1,3, condensed with a carbocyclic ring
-
- 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
- A01N49/00—Biocides, pest repellants or attractants, or plant growth regulators, containing compounds containing the group, wherein m+n>=1, both X together may also mean —Y— or a direct carbon-to-carbon bond, and the carbon atoms marked with an asterisk are not part of any ring system other than that which may be formed by the atoms X, the carbon atoms in square brackets being part of any acyclic or cyclic structure, or the group, wherein A means a carbon atom or Y, n>=0, and not more than one of these carbon atoms being a member of the same ring system, e.g. juvenile insect hormones or mimics thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
- C07D317/62—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring 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 atoms of the carbocyclic ring
- C07D317/64—Oxygen atoms
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Plant Pathology (AREA)
- Pest Control & Pesticides (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Insects & Arthropods (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Priority Applications (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CA130220A CA919685A (en) | 1971-03-15 | 1971-12-15 | Ethers having juvenile hormone activity |
| ZA718451A ZA718451B (en) | 1971-03-15 | 1971-12-17 | 4-alkoxy-1,2-methylenedioxybenzenes |
| DE2164746A DE2164746A1 (de) | 1971-03-15 | 1971-12-27 | 4-alkoxy-1,2-methylendioxybenzole |
| CH1918971A CH564007A5 (enrdf_load_stackoverflow) | 1971-03-15 | 1971-12-30 | |
| NL7200264A NL7200264A (enrdf_load_stackoverflow) | 1971-03-15 | 1972-01-07 | |
| FR7200792A FR2167260A1 (en) | 1971-03-15 | 1972-01-11 | 3-alkoxy-1,2-methylene dioxy-benzenes - arthropod growth regulators |
| BE778058A BE778058A (fr) | 1971-03-15 | 1972-01-14 | 4-alcoxy-1,2-methylenedioxy-benzene, leur preparation et leur usage |
Applications Claiming Priority (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US12457071A | 1971-03-15 | 1971-03-15 | |
| CA130220A CA919685A (en) | 1971-03-15 | 1971-12-15 | Ethers having juvenile hormone activity |
| ZA718451A ZA718451B (en) | 1971-03-15 | 1971-12-17 | 4-alkoxy-1,2-methylenedioxybenzenes |
| DE2164746A DE2164746A1 (de) | 1971-03-15 | 1971-12-27 | 4-alkoxy-1,2-methylendioxybenzole |
| CH1918971A CH564007A5 (enrdf_load_stackoverflow) | 1971-03-15 | 1971-12-30 | |
| NL7200264A NL7200264A (enrdf_load_stackoverflow) | 1971-03-15 | 1972-01-07 | |
| FR7200792A FR2167260A1 (en) | 1971-03-15 | 1972-01-11 | 3-alkoxy-1,2-methylene dioxy-benzenes - arthropod growth regulators |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH564007A5 true CH564007A5 (enrdf_load_stackoverflow) | 1975-07-15 |
Family
ID=27560861
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1918971A CH564007A5 (enrdf_load_stackoverflow) | 1971-03-15 | 1971-12-30 |
Country Status (7)
| Country | Link |
|---|---|
| BE (1) | BE778058A (enrdf_load_stackoverflow) |
| CA (1) | CA919685A (enrdf_load_stackoverflow) |
| CH (1) | CH564007A5 (enrdf_load_stackoverflow) |
| DE (1) | DE2164746A1 (enrdf_load_stackoverflow) |
| FR (1) | FR2167260A1 (enrdf_load_stackoverflow) |
| NL (1) | NL7200264A (enrdf_load_stackoverflow) |
| ZA (1) | ZA718451B (enrdf_load_stackoverflow) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2378409A1 (en) * | 1999-07-23 | 2001-02-01 | Bioparken As | Control of crustacean infestation of aquatic animals |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2570971A (en) * | 1970-02-26 | 1972-08-24 | Zoecon Corporation | Compounds and syntheses |
-
1971
- 1971-12-15 CA CA130220A patent/CA919685A/en not_active Expired
- 1971-12-17 ZA ZA718451A patent/ZA718451B/xx unknown
- 1971-12-27 DE DE2164746A patent/DE2164746A1/de active Pending
- 1971-12-30 CH CH1918971A patent/CH564007A5/de not_active IP Right Cessation
-
1972
- 1972-01-07 NL NL7200264A patent/NL7200264A/xx unknown
- 1972-01-11 FR FR7200792A patent/FR2167260A1/fr active Granted
- 1972-01-14 BE BE778058A patent/BE778058A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| ZA718451B (en) | 1972-09-27 |
| BE778058A (fr) | 1972-07-14 |
| DE2164746A1 (de) | 1973-07-12 |
| CA919685A (en) | 1973-01-23 |
| FR2167260B1 (enrdf_load_stackoverflow) | 1976-06-11 |
| NL7200264A (enrdf_load_stackoverflow) | 1973-07-10 |
| FR2167260A1 (en) | 1973-08-24 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased | ||
| PL | Patent ceased |