JPS631300B2 - - Google Patents
Info
- Publication number
- JPS631300B2 JPS631300B2 JP54077623A JP7762379A JPS631300B2 JP S631300 B2 JPS631300 B2 JP S631300B2 JP 54077623 A JP54077623 A JP 54077623A JP 7762379 A JP7762379 A JP 7762379A JP S631300 B2 JPS631300 B2 JP S631300B2
- Authority
- JP
- Japan
- Prior art keywords
- carbon
- general formula
- here
- following general
- same
- 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
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 claims description 34
- 150000001875 compounds Chemical class 0.000 claims description 25
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 20
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 16
- 229910052801 chlorine Inorganic materials 0.000 claims description 13
- 239000000203 mixture Substances 0.000 claims description 11
- 239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 10
- 238000004519 manufacturing process Methods 0.000 claims description 10
- 229910052731 fluorine Inorganic materials 0.000 claims description 9
- 241000607479 Yersinia pestis Species 0.000 claims description 7
- IQJCJNWUQCTSBB-UHFFFAOYSA-N 1,4-bis(5-chloropent-4-ynoxy)benzene Chemical compound ClC#CCCCOC1=CC=C(OCCCC#CCl)C=C1 IQJCJNWUQCTSBB-UHFFFAOYSA-N 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 5
- LYALJRUXUYBQHA-UHFFFAOYSA-N 1-(5,5-dichloropent-4-enoxy)-4-[(4-methylphenyl)methoxy]benzene Chemical group C1=CC(C)=CC=C1COC1=CC=C(OCCCC=C(Cl)Cl)C=C1 LYALJRUXUYBQHA-UHFFFAOYSA-N 0.000 claims description 4
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 4
- 229910052794 bromium Inorganic materials 0.000 claims description 4
- BYBDXJRBVAZYNO-UHFFFAOYSA-N 1-(5,5-dichloropent-4-enoxy)-4-phenoxybenzene Chemical compound C1=CC(OCCCC=C(Cl)Cl)=CC=C1OC1=CC=CC=C1 BYBDXJRBVAZYNO-UHFFFAOYSA-N 0.000 claims description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 229910052740 iodine Inorganic materials 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 206010061217 Infestation Diseases 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 3
- NJRVQXAOVMPYSD-UHFFFAOYSA-N 1,4-bis(5,5-dichloropent-4-enoxy)benzene Chemical compound ClC(Cl)=CCCCOC1=CC=C(OCCCC=C(Cl)Cl)C=C1 NJRVQXAOVMPYSD-UHFFFAOYSA-N 0.000 claims 1
- YYRGGOGFJVSOSJ-UHFFFAOYSA-N 1,4-bis(5,5-difluoropent-4-enoxy)benzene Chemical compound FC(=CCCCOC1=CC=C(C=C1)OCCCC=C(F)F)F YYRGGOGFJVSOSJ-UHFFFAOYSA-N 0.000 claims 1
- XVPURBDFBRMKLI-UHFFFAOYSA-N 1,4-bis(5-chloro-5-fluoropent-4-enoxy)benzene Chemical compound ClC(=CCCCOC1=CC=C(C=C1)OCCCC=C(Cl)F)F XVPURBDFBRMKLI-UHFFFAOYSA-N 0.000 claims 1
- GYINVKUFEYYUBI-UHFFFAOYSA-N 1-(5,5-dichloropent-4-enoxy)-4-phenylmethoxybenzene Chemical compound C1=CC(OCCCC=C(Cl)Cl)=CC=C1OCC1=CC=CC=C1 GYINVKUFEYYUBI-UHFFFAOYSA-N 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 claims 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 claims 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims 1
- 125000001246 bromo group Chemical group Br* 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 230000009545 invasion Effects 0.000 claims 1
- 125000002346 iodo group Chemical group I* 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 230000000694 effects Effects 0.000 description 8
- 238000000034 method Methods 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- 235000013601 eggs Nutrition 0.000 description 6
- 229910052739 hydrogen Inorganic materials 0.000 description 6
- 239000001257 hydrogen Substances 0.000 description 6
- 239000002949 juvenile hormone Substances 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 150000002431 hydrogen Chemical class 0.000 description 5
- 229930014550 juvenile hormone Natural products 0.000 description 5
- 150000003633 juvenile hormone derivatives Chemical class 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- ZSBDGXGICLIJGD-UHFFFAOYSA-N 4-phenoxyphenol Chemical compound C1=CC(O)=CC=C1OC1=CC=CC=C1 ZSBDGXGICLIJGD-UHFFFAOYSA-N 0.000 description 4
- 241000239290 Araneae Species 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 230000003054 hormonal effect Effects 0.000 description 4
- -1 hydroquinone ethers Chemical class 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- 241000256111 Aedes <genus> Species 0.000 description 3
- 241001060517 Dicranolaius bellulus Species 0.000 description 3
- 230000000895 acaricidal effect Effects 0.000 description 3
- 150000001447 alkali salts Chemical class 0.000 description 3
- 238000006704 dehydrohalogenation reaction Methods 0.000 description 3
- 241000894007 species Species 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 150000003505 terpenes Chemical group 0.000 description 3
- NGSBBMWYTNYYSI-UHFFFAOYSA-N 1,5-dichloropent-1-yne Chemical compound ClCCCC#CCl NGSBBMWYTNYYSI-UHFFFAOYSA-N 0.000 description 2
- UGBCWXMJTSSSNL-UHFFFAOYSA-N 4-(5,5-dichloropent-4-enoxy)phenol Chemical compound OC1=CC=C(OCCCC=C(Cl)Cl)C=C1 UGBCWXMJTSSSNL-UHFFFAOYSA-N 0.000 description 2
- 241000238876 Acari Species 0.000 description 2
- 244000046052 Phaseolus vulgaris Species 0.000 description 2
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 2
- 241000254109 Tenebrio molitor Species 0.000 description 2
- 241001454293 Tetranychus urticae Species 0.000 description 2
- 230000002159 abnormal effect Effects 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 230000004071 biological effect Effects 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 229960001760 dimethyl sulfoxide Drugs 0.000 description 2
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical class C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 230000001747 exhibiting effect Effects 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 235000015097 nutrients Nutrition 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 2
- VZEWJVRACUZHQR-UHFFFAOYSA-N 1,1,1,5-tetrachloropentane Chemical compound ClCCCCC(Cl)(Cl)Cl VZEWJVRACUZHQR-UHFFFAOYSA-N 0.000 description 1
- WIBRQEFYLKNRTM-UHFFFAOYSA-N 1,1,5-trichloropent-1-ene Chemical compound ClCCCC=C(Cl)Cl WIBRQEFYLKNRTM-UHFFFAOYSA-N 0.000 description 1
- DMHZDOTYAVHSEH-UHFFFAOYSA-N 1-(chloromethyl)-4-methylbenzene Chemical compound CC1=CC=C(CCl)C=C1 DMHZDOTYAVHSEH-UHFFFAOYSA-N 0.000 description 1
- 241000256118 Aedes aegypti Species 0.000 description 1
- 241000254173 Coleoptera Species 0.000 description 1
- 241001127120 Dysdercus fasciatus Species 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 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
- OWYWGLHRNBIFJP-UHFFFAOYSA-N Ipazine Chemical compound CCN(CC)C1=NC(Cl)=NC(NC(C)C)=N1 OWYWGLHRNBIFJP-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 241000382353 Pupa Species 0.000 description 1
- 241001454295 Tetranychidae Species 0.000 description 1
- 150000007824 aliphatic compounds Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000003651 drinking water Substances 0.000 description 1
- 235000020188 drinking water Nutrition 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- 238000006266 etherification reaction Methods 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000005556 hormone Substances 0.000 description 1
- 229940088597 hormone Drugs 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 230000000366 juvenile effect Effects 0.000 description 1
- 230000001418 larval effect Effects 0.000 description 1
- 230000036244 malformation Effects 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
Classifications
-
- 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
- A01N31/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic oxygen or sulfur compounds
- A01N31/08—Oxygen or sulfur directly attached to an aromatic ring system
- A01N31/16—Oxygen or sulfur directly attached to an aromatic ring system with two or more oxygen or sulfur atoms directly attached to the same aromatic ring system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
- C07C43/225—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring containing halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
- C07C43/23—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring containing hydroxy or O-metal groups
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth 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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT24794/78A IT1096582B (it) | 1978-06-21 | 1978-06-21 | Dieteri idrochinonici aventi attivita' ormonica giovanile e acaricida |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5511577A JPS5511577A (en) | 1980-01-26 |
| JPS631300B2 true JPS631300B2 (enrdf_load_stackoverflow) | 1988-01-12 |
Family
ID=11214759
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP7762379A Granted JPS5511577A (en) | 1978-06-21 | 1979-06-21 | Hydroquinone diether having young hormone activity and miticide activity |
Country Status (3)
| Country | Link |
|---|---|
| JP (1) | JPS5511577A (enrdf_load_stackoverflow) |
| BE (1) | BE877164A (enrdf_load_stackoverflow) |
| IT (1) | IT1096582B (enrdf_load_stackoverflow) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2023591B (en) * | 1978-06-21 | 1982-10-06 | Montedison Spa | Hydroquinone diethers having a juvenile hormonic and acaricide activity |
| IT1190667B (it) * | 1982-01-22 | 1988-02-24 | Montedison Spa | Metodo di lotta contro infestazioni di formiche |
| DE3125059A1 (de) * | 1981-06-26 | 1983-01-05 | Bayer Ag, 5090 Leverkusen | Dioxybenzoletherderivate, diese enthaltende arzneimittel, verfahren zu ihrer herstellung und ihre verwendung |
-
1978
- 1978-06-21 IT IT24794/78A patent/IT1096582B/it active
-
1979
- 1979-06-21 BE BE0/195880A patent/BE877164A/fr not_active IP Right Cessation
- 1979-06-21 JP JP7762379A patent/JPS5511577A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5511577A (en) | 1980-01-26 |
| IT1096582B (it) | 1985-08-26 |
| BE877164A (fr) | 1979-12-21 |
| IT7824794A0 (it) | 1978-06-21 |
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