GB1436621A - Aromatic alkyl ethers and thioethers and their use in insecticidal and acaricidal compositions - Google Patents
Aromatic alkyl ethers and thioethers and their use in insecticidal and acaricidal compositionsInfo
- Publication number
- GB1436621A GB1436621A GB2882273A GB2882273A GB1436621A GB 1436621 A GB1436621 A GB 1436621A GB 2882273 A GB2882273 A GB 2882273A GB 2882273 A GB2882273 A GB 2882273A GB 1436621 A GB1436621 A GB 1436621A
- Authority
- GB
- United Kingdom
- Prior art keywords
- formula
- compound
- bromo
- alkyl
- isopentyloxy
- 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
- -1 Aromatic alkyl ethers Chemical class 0.000 title abstract 2
- 230000000895 acaricidal effect Effects 0.000 title abstract 2
- 150000003568 thioethers Chemical class 0.000 title abstract 2
- 230000000749 insecticidal effect Effects 0.000 title 1
- 239000000203 mixture Substances 0.000 title 1
- 150000001875 compounds Chemical class 0.000 abstract 22
- 125000000217 alkyl group Chemical group 0.000 abstract 7
- 239000002253 acid Substances 0.000 abstract 6
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 abstract 4
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 abstract 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 abstract 4
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 4
- 229910000104 sodium hydride Inorganic materials 0.000 abstract 4
- 239000012312 sodium hydride Substances 0.000 abstract 4
- 229910052799 carbon Inorganic materials 0.000 abstract 3
- ULTHEAFYOOPTTB-UHFFFAOYSA-N 1,4-dibromobutane Chemical compound BrCCCCBr ULTHEAFYOOPTTB-UHFFFAOYSA-N 0.000 abstract 2
- UTLCXFYPJRYKLD-UHFFFAOYSA-N 1-(4-bromobutoxy)-3-methylbutane Chemical compound CC(C)CCOCCCCBr UTLCXFYPJRYKLD-UHFFFAOYSA-N 0.000 abstract 2
- JAUSEOYIDXDKLA-UHFFFAOYSA-N 4-(3-methylbutoxy)butan-1-ol Chemical compound CC(C)CCOCCCCO JAUSEOYIDXDKLA-UHFFFAOYSA-N 0.000 abstract 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 abstract 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 2
- 125000003342 alkenyl group Chemical group 0.000 abstract 2
- 125000000304 alkynyl group Chemical group 0.000 abstract 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 abstract 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 abstract 2
- DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-UHFFFAOYSA-N 0.000 abstract 2
- KYXVWWDJGOJMER-UHFFFAOYSA-N 1-(4-bromobutoxy)-4-methylsulfanylbenzene Chemical compound CSC1=CC=C(OCCCCBr)C=C1 KYXVWWDJGOJMER-UHFFFAOYSA-N 0.000 abstract 1
- ANZIXUWUHQXQFI-UHFFFAOYSA-N 1-bromo-1-propan-2-yloxyhexane Chemical compound CCCCCC(Br)OC(C)C ANZIXUWUHQXQFI-UHFFFAOYSA-N 0.000 abstract 1
- YXZFFTJAHVMMLF-UHFFFAOYSA-N 1-bromo-3-methylbutane Chemical compound CC(C)CCBr YXZFFTJAHVMMLF-UHFFFAOYSA-N 0.000 abstract 1
- WVRIKFXUCRGTGI-UHFFFAOYSA-N 1-bromo-6-(3-methylbutoxy)hexane Chemical compound CC(C)CCOCCCCCCBr WVRIKFXUCRGTGI-UHFFFAOYSA-N 0.000 abstract 1
- CSGOVVXCRLXRDS-UHFFFAOYSA-N 1-bromo-6-[4-(3-methylbutoxy)butoxy]hexane Chemical compound CC(C)CCOCCCCOCCCCCCBr CSGOVVXCRLXRDS-UHFFFAOYSA-N 0.000 abstract 1
- HCDWXULPAMKFOU-UHFFFAOYSA-N 2-(1,3-benzodioxol-5-ylmethylsulfanyl)ethanol Chemical compound OCCSCC1=CC=C2OCOC2=C1 HCDWXULPAMKFOU-UHFFFAOYSA-N 0.000 abstract 1
- QASBCTGZKABPKX-UHFFFAOYSA-N 4-(methylsulfanyl)phenol Chemical compound CSC1=CC=C(O)C=C1 QASBCTGZKABPKX-UHFFFAOYSA-N 0.000 abstract 1
- OYVUCQVIHYMROV-UHFFFAOYSA-N 4-propan-2-yloxybutan-1-ol Chemical compound CC(C)OCCCCO OYVUCQVIHYMROV-UHFFFAOYSA-N 0.000 abstract 1
- UNYHRXLMTSXVIB-UHFFFAOYSA-N 5-(bromomethyl)-1,3-benzodioxole Chemical compound BrCC1=CC=C2OCOC2=C1 UNYHRXLMTSXVIB-UHFFFAOYSA-N 0.000 abstract 1
- CPFHEVYJRPAAAY-UHFFFAOYSA-N 6-(3-methylbutoxy)hexan-1-ol Chemical compound CC(C)CCOCCCCCCO CPFHEVYJRPAAAY-UHFFFAOYSA-N 0.000 abstract 1
- JHFWBLIBTOSSOA-UHFFFAOYSA-N 6-[4-(3-methylbutoxy)butoxy]hexan-1-ol Chemical compound CC(C)CCOCCCCOCCCCCCO JHFWBLIBTOSSOA-UHFFFAOYSA-N 0.000 abstract 1
- QYYMIAMZSVSARL-UHFFFAOYSA-N 6-[6-(3-methylbutoxy)hexoxy]hexan-1-ol Chemical compound CC(C)CCOCCCCCCOCCCCCCO QYYMIAMZSVSARL-UHFFFAOYSA-N 0.000 abstract 1
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 abstract 1
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 abstract 1
- 239000000642 acaricide Substances 0.000 abstract 1
- 125000003302 alkenyloxy group Chemical group 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000005115 alkyl carbamoyl group Chemical group 0.000 abstract 1
- 125000004448 alkyl carbonyl group Chemical group 0.000 abstract 1
- 125000004414 alkyl thio group Chemical group 0.000 abstract 1
- 239000011230 binding agent Substances 0.000 abstract 1
- 239000001273 butane Substances 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 abstract 1
- 239000002917 insecticide Substances 0.000 abstract 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract 1
- 229910052708 sodium Inorganic materials 0.000 abstract 1
- 239000011734 sodium Substances 0.000 abstract 1
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/03—Ethers having all ether-oxygen atoms bound to acyclic carbon atoms
- C07C43/04—Saturated ethers
- C07C43/12—Saturated ethers containing halogen
- C07C43/126—Saturated ethers containing halogen having more than one ether bond
-
- 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
- C07C43/205—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring the aromatic ring being a non-condensed ring
- C07C43/2055—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring the aromatic ring being a non-condensed ring containing more than one ether bond
-
- 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
- C07C43/215—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring having unsaturation outside the six-membered aromatic rings
-
- 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
- C07D317/50—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to atoms of the carbocyclic ring
- C07D317/54—Radicals substituted by oxygen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH952072 | 1972-06-23 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1436621A true GB1436621A (en) | 1976-05-19 |
Family
ID=4352843
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2882273A Expired GB1436621A (en) | 1972-06-23 | 1973-06-18 | Aromatic alkyl ethers and thioethers and their use in insecticidal and acaricidal compositions |
Country Status (14)
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3144760C2 (de) * | 1981-11-11 | 1989-06-08 | W. Schlafhorst & Co, 4050 Mönchengladbach | Verfahren und Vorrichtung zum Steuern des Anspinnvorgangs bei einer Offenend-Rotorspinnmaschine |
| US5098477A (en) * | 1988-12-14 | 1992-03-24 | Ciba-Geigy Corporation | Inks, particularly for ink printing |
-
1973
- 1973-06-18 GB GB2882273A patent/GB1436621A/en not_active Expired
- 1973-06-21 CS CS4463A patent/CS172397B2/cs unknown
- 1973-06-21 FR FR7322692A patent/FR2198919B1/fr not_active Expired
- 1973-06-21 SU SU1938803A patent/SU541428A3/ru active
- 1973-06-21 DD DD177594*A patent/DD110748A5/xx unknown
- 1973-06-21 DD DD171729A patent/DD107897A5/xx unknown
- 1973-06-21 IL IL42578A patent/IL42578A0/xx unknown
- 1973-06-21 HU HUSA2504A patent/HU169387B/hu unknown
- 1973-06-22 IT IT50967/73A patent/IT989674B/it active
- 1973-06-22 ZA ZA00734248A patent/ZA734248B/xx unknown
- 1973-06-22 BR BR4646/73A patent/BR7304646D0/pt unknown
- 1973-06-22 DE DE2331719A patent/DE2331719A1/de active Pending
- 1973-06-22 ES ES73416170A patent/ES416170A1/es not_active Expired
- 1973-06-23 JP JP48071217A patent/JPS5214295B2/ja not_active Expired
- 1973-06-25 AU AU57318/73A patent/AU5731873A/en not_active Expired
-
1976
- 1976-03-11 JP JP51026967A patent/JPS51125033A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| FR2198919B1 (enrdf_load_stackoverflow) | 1977-05-13 |
| SU541428A3 (ru) | 1976-12-30 |
| BR7304646D0 (pt) | 1974-08-29 |
| CS172397B2 (enrdf_load_stackoverflow) | 1976-12-29 |
| DD110748A5 (enrdf_load_stackoverflow) | 1975-01-12 |
| FR2198919A1 (enrdf_load_stackoverflow) | 1974-04-05 |
| JPS50100232A (enrdf_load_stackoverflow) | 1975-08-08 |
| IT989674B (it) | 1975-06-10 |
| AU5731873A (en) | 1975-01-09 |
| ZA734248B (en) | 1975-02-26 |
| DD107897A5 (enrdf_load_stackoverflow) | 1974-08-20 |
| JPS5214295B2 (enrdf_load_stackoverflow) | 1977-04-20 |
| IL42578A0 (en) | 1973-08-29 |
| ES416170A1 (es) | 1976-07-01 |
| JPS51125033A (en) | 1976-11-01 |
| DE2331719A1 (de) | 1974-01-10 |
| HU169387B (enrdf_load_stackoverflow) | 1976-11-28 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| PLNP | Patent lapsed through nonpayment of renewal fees |