DE2102539A1 - Neue Phenylather - Google Patents
Neue PhenylatherInfo
- Publication number
- DE2102539A1 DE2102539A1 DE19712102539 DE2102539A DE2102539A1 DE 2102539 A1 DE2102539 A1 DE 2102539A1 DE 19712102539 DE19712102539 DE 19712102539 DE 2102539 A DE2102539 A DE 2102539A DE 2102539 A1 DE2102539 A1 DE 2102539A1
- Authority
- DE
- Germany
- Prior art keywords
- formula
- compounds according
- chlorine
- stands
- compounds
- 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.)
- Pending
Links
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical class C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims description 12
- 241000238631 Hexapoda Species 0.000 claims description 10
- 125000003342 alkenyl group Chemical group 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 5
- 229910052801 chlorine Inorganic materials 0.000 claims description 5
- 239000000460 chlorine Substances 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 229940100198 alkylating agent Drugs 0.000 claims description 4
- 239000002168 alkylating agent Substances 0.000 claims description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
- 229910052794 bromium Inorganic materials 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- 150000002989 phenols Chemical class 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- 229910052731 fluorine Inorganic materials 0.000 claims 2
- 239000011737 fluorine Substances 0.000 claims 2
- 125000001246 bromo group Chemical group Br* 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 13
- -1 potassium carbonate or alkali metal alkoxide Chemical class 0.000 description 9
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 230000000366 juvenile effect Effects 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- JSCUZAYKVZXKQE-JXMROGBWSA-N (2e)-1-bromo-3,7-dimethylocta-2,6-diene Chemical compound CC(C)=CCC\C(C)=C\CBr JSCUZAYKVZXKQE-JXMROGBWSA-N 0.000 description 2
- BTJIUGUIPKRLHP-UHFFFAOYSA-N 4-nitrophenol Chemical compound OC1=CC=C([N+]([O-])=O)C=C1 BTJIUGUIPKRLHP-UHFFFAOYSA-N 0.000 description 2
- QPKCDMXLSDFCQD-UHFFFAOYSA-N 8-bromo-2,6-dimethyloct-2-ene Chemical compound BrCCC(C)CCC=C(C)C QPKCDMXLSDFCQD-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 241000255925 Diptera Species 0.000 description 2
- 241000258937 Hemiptera Species 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 238000006735 epoxidation reaction Methods 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 150000002500 ions Chemical class 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
- 238000001819 mass spectrum Methods 0.000 description 2
- 230000029052 metamorphosis Effects 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- MFJMZOUFSWSBNV-UHFFFAOYSA-N 1-chloro-2-(2-chlorophenoxy)benzene Chemical compound ClC1=CC=CC=C1OC1=CC=CC=C1Cl MFJMZOUFSWSBNV-UHFFFAOYSA-N 0.000 description 1
- MWAGUKZCDDRDCS-UHFFFAOYSA-N 1-nitro-4-(4-nitrophenoxy)benzene Chemical compound C1=CC([N+](=O)[O-])=CC=C1OC1=CC=C([N+]([O-])=O)C=C1 MWAGUKZCDDRDCS-UHFFFAOYSA-N 0.000 description 1
- WWGQHTJIFOQAOC-UHFFFAOYSA-N 2,3,5-trichlorophenol Chemical compound OC1=CC(Cl)=CC(Cl)=C1Cl WWGQHTJIFOQAOC-UHFFFAOYSA-N 0.000 description 1
- UMPSXRYVXUPCOS-UHFFFAOYSA-N 2,3-dichlorophenol Chemical compound OC1=CC=CC(Cl)=C1Cl UMPSXRYVXUPCOS-UHFFFAOYSA-N 0.000 description 1
- LHJGJYXLEPZJPM-UHFFFAOYSA-N 2,4,5-trichlorophenol Chemical compound OC1=CC(Cl)=C(Cl)C=C1Cl LHJGJYXLEPZJPM-UHFFFAOYSA-N 0.000 description 1
- LINPIYWFGCPVIE-UHFFFAOYSA-N 2,4,6-trichlorophenol Chemical compound OC1=C(Cl)C=C(Cl)C=C1Cl LINPIYWFGCPVIE-UHFFFAOYSA-N 0.000 description 1
- UFBJCMHMOXMLKC-UHFFFAOYSA-N 2,4-dinitrophenol Chemical compound OC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O UFBJCMHMOXMLKC-UHFFFAOYSA-N 0.000 description 1
- GLVYLTSKTCWWJR-UHFFFAOYSA-N 2-carbonoperoxoylbenzoic acid Chemical compound OOC(=O)C1=CC=CC=C1C(O)=O GLVYLTSKTCWWJR-UHFFFAOYSA-N 0.000 description 1
- AKLOLDQYWQAREW-UHFFFAOYSA-N 3,4-dinitrophenol Chemical compound OC1=CC=C([N+]([O-])=O)C([N+]([O-])=O)=C1 AKLOLDQYWQAREW-UHFFFAOYSA-N 0.000 description 1
- WXNZTHHGJRFXKQ-UHFFFAOYSA-N 4-chlorophenol Chemical compound OC1=CC=C(Cl)C=C1 WXNZTHHGJRFXKQ-UHFFFAOYSA-N 0.000 description 1
- DCIPFSYBGTWYCR-UHFFFAOYSA-N 5847-59-6 Chemical compound OC1=CC=C([N+]([O-])=O)C=C1Br DCIPFSYBGTWYCR-UHFFFAOYSA-N 0.000 description 1
- 241001124076 Aphididae Species 0.000 description 1
- 241001674044 Blattodea Species 0.000 description 1
- 241000254173 Coleoptera Species 0.000 description 1
- 241001513837 Dermestes maculatus Species 0.000 description 1
- 241001425472 Dysdercus cingulatus Species 0.000 description 1
- 241001454728 Gelechiidae Species 0.000 description 1
- 241001464731 Graphosoma italicum Species 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 241000255777 Lepidoptera Species 0.000 description 1
- 241000258912 Lygaeidae Species 0.000 description 1
- 241001414825 Miridae Species 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 241000255893 Pyralidae Species 0.000 description 1
- 241001510071 Pyrrhocoridae Species 0.000 description 1
- 241001502122 Pyrrhocoris apterus Species 0.000 description 1
- 241000254109 Tenebrio molitor Species 0.000 description 1
- 241000254107 Tenebrionidae Species 0.000 description 1
- 230000003187 abdominal effect Effects 0.000 description 1
- 230000002159 abnormal effect Effects 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000010410 dusting Methods 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 239000002418 insect attractant Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 230000007653 larval development Effects 0.000 description 1
- 230000001418 larval effect Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000004660 morphological change Effects 0.000 description 1
- 239000000025 natural resin Substances 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 150000004967 organic peroxy acids Chemical class 0.000 description 1
- 230000001766 physiological effect Effects 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
- C07D303/18—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by etherified hydroxyl radicals
- C07D303/20—Ethers with hydroxy compounds containing no oxirane rings
- C07D303/22—Ethers with hydroxy compounds containing no oxirane rings with monohydroxy compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Epoxy Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS652A CS151875B1 (enExample) | 1970-01-29 | 1970-01-29 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2102539A1 true DE2102539A1 (de) | 1971-08-05 |
Family
ID=5339010
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19712102539 Pending DE2102539A1 (de) | 1970-01-29 | 1971-01-20 | Neue Phenylather |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US3711519A (enExample) |
| AU (1) | AU2430671A (enExample) |
| CS (1) | CS151875B1 (enExample) |
| DE (1) | DE2102539A1 (enExample) |
| FR (1) | FR2076978A5 (enExample) |
| NL (1) | NL7100558A (enExample) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3970758A (en) * | 1969-04-10 | 1976-07-20 | Stauffer Chemical Company | Certain geranyl phenyl ethers and their epoxides and their use in controlling insects |
| US4001339A (en) * | 1969-04-30 | 1977-01-04 | Hoffmann-La Roche Inc. | Phenyl derivatives |
| US3879429A (en) * | 1969-04-30 | 1975-04-22 | Hoffmann La Roche | Phenyl derivatives |
| US3888987A (en) * | 1971-11-04 | 1975-06-10 | Stauffer Chemical Co | Derivatives of certain geranyl phenyl ethers and their use in controlling insects |
| US3998855A (en) * | 1972-01-14 | 1976-12-21 | Ciba-Geigy Corporation | Epoxyalkoxy substituted benzophenones |
| US3953607A (en) * | 1973-03-21 | 1976-04-27 | The United States Of America As Represented By The Secretary Of Agriculture | Method of controlling insects using 7-ethoxy-1-(p-ethylphenoxy)-3,7-dimethyl-2-octene |
| US3873724A (en) * | 1973-03-21 | 1975-03-25 | Us Agriculture | Method for disrupting normal insect maturation |
| US3934033A (en) * | 1973-03-21 | 1976-01-20 | The United States Of America As Represented By The Secretary Of Agriculture | Method for distrupting normal insect maturation |
| US3968252A (en) * | 1973-07-05 | 1976-07-06 | Stauffer Chemical Company | Derivatives of certain geranyl phenyl ethers and their use in controlling insects |
| US4051262A (en) * | 1975-05-19 | 1977-09-27 | Stauffer Chemical Company | Certain geranyl phenyl ethers and their epoxides and their use in controlling insects |
-
1970
- 1970-01-29 CS CS652A patent/CS151875B1/cs unknown
-
1971
- 1971-01-13 AU AU24306/71A patent/AU2430671A/en not_active Expired
- 1971-01-15 NL NL7100558A patent/NL7100558A/xx unknown
- 1971-01-20 DE DE19712102539 patent/DE2102539A1/de active Pending
- 1971-01-22 US US00109024A patent/US3711519A/en not_active Expired - Lifetime
- 1971-01-26 FR FR7102442A patent/FR2076978A5/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| CS151875B1 (enExample) | 1973-11-19 |
| FR2076978A5 (enExample) | 1971-10-15 |
| US3711519A (en) | 1973-01-16 |
| AU2430671A (en) | 1972-07-20 |
| NL7100558A (enExample) | 1971-08-02 |
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