DE2511713C3 - Diels-Alder Addukte von Pentachlor-1-azacydopentadien und sie enthaltende insektizide Mittel - Google Patents
Diels-Alder Addukte von Pentachlor-1-azacydopentadien und sie enthaltende insektizide MittelInfo
- Publication number
- DE2511713C3 DE2511713C3 DE2511713A DE2511713A DE2511713C3 DE 2511713 C3 DE2511713 C3 DE 2511713C3 DE 2511713 A DE2511713 A DE 2511713A DE 2511713 A DE2511713 A DE 2511713A DE 2511713 C3 DE2511713 C3 DE 2511713C3
- Authority
- DE
- Germany
- Prior art keywords
- diels
- pentachloro
- compound
- azacydopentadiene
- insecticides
- 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
- 238000005698 Diels-Alder reaction Methods 0.000 title claims description 3
- 239000002917 insecticide Substances 0.000 title description 17
- WIDRTZBFYMLWCZ-UHFFFAOYSA-N 2,2,3,4,5-pentachloropyrrole Chemical compound ClC1=NC(Cl)(Cl)C(Cl)=C1Cl WIDRTZBFYMLWCZ-UHFFFAOYSA-N 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 description 25
- 239000000460 chlorine Substances 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- 230000000694 effects Effects 0.000 description 8
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 241001674048 Phthiraptera Species 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 210000002268 wool Anatomy 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 241000517324 Pediculidae Species 0.000 description 4
- 241000607479 Yersinia pestis Species 0.000 description 4
- 208000028454 lice infestation Diseases 0.000 description 4
- 231100000331 toxic Toxicity 0.000 description 4
- 230000002588 toxic effect Effects 0.000 description 4
- 241001674044 Blattodea Species 0.000 description 3
- 241000256113 Culicidae Species 0.000 description 3
- 241000238631 Hexapoda Species 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 241000255925 Diptera Species 0.000 description 2
- 241000305186 Persectania ewingii Species 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 125000001246 bromo group Chemical group Br* 0.000 description 2
- 239000012876 carrier material Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 125000000753 cycloalkyl group Chemical group 0.000 description 2
- DFBKLUNHFCTMDC-PICURKEMSA-N dieldrin Chemical compound C([C@H]1[C@H]2[C@@]3(Cl)C(Cl)=C([C@]([C@H]22)(Cl)C3(Cl)Cl)Cl)[C@H]2[C@@H]2[C@H]1O2 DFBKLUNHFCTMDC-PICURKEMSA-N 0.000 description 2
- 229950006824 dieldrin Drugs 0.000 description 2
- NGPMUTDCEIKKFM-UHFFFAOYSA-N dieldrin Natural products CC1=C(Cl)C2(Cl)C3C4CC(C5OC45)C3C1(Cl)C2(Cl)Cl NGPMUTDCEIKKFM-UHFFFAOYSA-N 0.000 description 2
- 230000000749 insecticidal effect Effects 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- SJYNFBVQFBRSIB-UHFFFAOYSA-N norbornadiene Chemical compound C1=CC2C=CC1C2 SJYNFBVQFBRSIB-UHFFFAOYSA-N 0.000 description 2
- 125000004430 oxygen atom Chemical group O* 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 231100000419 toxicity Toxicity 0.000 description 2
- 230000001988 toxicity Effects 0.000 description 2
- RWBPZWYPNNSWNR-UHFFFAOYSA-N 4,5,6,9,9-pentachloro-2,2a,6,6a,7,7a-hexahydro-1ah-2,7:3,6-dimethanooxireno[g]quinoline Chemical compound C12N(C3(Cl)Cl)C(Cl)=C(Cl)C3(Cl)C2C2CC1C1C2O1 RWBPZWYPNNSWNR-UHFFFAOYSA-N 0.000 description 1
- 241000256186 Anopheles <genus> Species 0.000 description 1
- 244000045232 Canavalia ensiformis Species 0.000 description 1
- 238000006117 Diels-Alder cycloaddition reaction Methods 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- 241000257303 Hymenoptera Species 0.000 description 1
- 241000256602 Isoptera Species 0.000 description 1
- 239000005949 Malathion Substances 0.000 description 1
- 241000517306 Pediculus humanus corporis Species 0.000 description 1
- 235000010617 Phaseolus lunatus Nutrition 0.000 description 1
- 208000005374 Poisoning Diseases 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 238000007259 addition reaction Methods 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000012490 blank solution Substances 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 210000003169 central nervous system Anatomy 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 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 1
- BIWJNBZANLAXMG-UHFFFAOYSA-N chlordane Chemical compound ClC1=C(Cl)C2(Cl)C3CC(Cl)C(Cl)C3C1(Cl)C2(Cl)Cl BIWJNBZANLAXMG-UHFFFAOYSA-N 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 238000006352 cycloaddition reaction Methods 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- JXSJBGJIGXNWCI-UHFFFAOYSA-N diethyl 2-[(dimethoxyphosphorothioyl)thio]succinate Chemical compound CCOC(=O)CC(SP(=S)(OC)OC)C(=O)OCC JXSJBGJIGXNWCI-UHFFFAOYSA-N 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 210000000609 ganglia Anatomy 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 230000002147 killing effect Effects 0.000 description 1
- 229960000453 malathion Drugs 0.000 description 1
- 210000000653 nervous system Anatomy 0.000 description 1
- 150000002829 nitrogen Chemical class 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- -1 pentachlorophenol-1-azacyclopentadien Chemical compound 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 231100000572 poisoning Toxicity 0.000 description 1
- 230000000607 poisoning effect Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000005180 public health Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000012088 reference solution Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 239000012085 test solution Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/08—Bridged systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US45457674A | 1974-03-25 | 1974-03-25 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2511713A1 DE2511713A1 (de) | 1975-10-09 |
| DE2511713B2 DE2511713B2 (de) | 1979-05-17 |
| DE2511713C3 true DE2511713C3 (de) | 1980-01-10 |
Family
ID=23805181
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2511713A Expired DE2511713C3 (de) | 1974-03-25 | 1975-03-18 | Diels-Alder Addukte von Pentachlor-1-azacydopentadien und sie enthaltende insektizide Mittel |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US4081448A (enExample) |
| JP (1) | JPS50157526A (enExample) |
| AR (1) | AR217037A1 (enExample) |
| BE (1) | BE827123A (enExample) |
| BR (1) | BR7501750A (enExample) |
| CA (1) | CA1048033A (enExample) |
| DE (1) | DE2511713C3 (enExample) |
| ES (1) | ES436006A1 (enExample) |
| FR (1) | FR2304612A1 (enExample) |
| GB (1) | GB1496277A (enExample) |
| IL (1) | IL46848A (enExample) |
| IT (1) | IT1049375B (enExample) |
| NL (1) | NL7503468A (enExample) |
| ZA (1) | ZA751497B (enExample) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2355843A1 (fr) * | 1976-06-23 | 1978-01-20 | Research Corp | Amines polycycliques chlorees utilisables comme insecticides |
| US4228078A (en) * | 1976-09-22 | 1980-10-14 | Research Corporation | Polycyclic chlorinated hydrocarbons containing bridgehead or imino nitrogen |
| US4284563A (en) * | 1978-02-08 | 1981-08-18 | Research Corporation | 9,10,11,12,12-Pentachloro 4,6-dioxa-5-thia-1-aza-tricyclo[7.2.1.02,8 ]d |
| US4322528A (en) * | 1979-01-31 | 1982-03-30 | Research Corporation | Polycyclic chlorinated hydrocarbons containing bridgehead or imino nitrogen |
| US4415704A (en) * | 1980-06-06 | 1983-11-15 | The Goodyear Tire & Rubber Company | Elastomeric interpolymer blends |
| CA3047896C (en) | 2016-12-27 | 2021-11-09 | Nihon Nohyaku Co., Ltd. | 4h-pyrrolopyridine compound or salt thereof, agricultural and horticultural insecticide comprising the compound or the salt, and method for using the insecticide |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3218355A (en) * | 1964-10-28 | 1965-11-16 | Du Pont | Halogenated adamantane derivatives |
-
1975
- 1975-03-11 ZA ZA00751497A patent/ZA751497B/xx unknown
- 1975-03-17 IL IL46848A patent/IL46848A/xx unknown
- 1975-03-18 DE DE2511713A patent/DE2511713C3/de not_active Expired
- 1975-03-20 AR AR258057A patent/AR217037A1/es active
- 1975-03-21 FR FR7508932A patent/FR2304612A1/fr active Granted
- 1975-03-21 CA CA222,754A patent/CA1048033A/en not_active Expired
- 1975-03-21 IT IT21518/75A patent/IT1049375B/it active
- 1975-03-24 BR BR1750/75A patent/BR7501750A/pt unknown
- 1975-03-24 GB GB12100/75A patent/GB1496277A/en not_active Expired
- 1975-03-24 NL NL7503468A patent/NL7503468A/xx not_active Application Discontinuation
- 1975-03-24 JP JP50035276A patent/JPS50157526A/ja active Pending
- 1975-03-25 ES ES436006A patent/ES436006A1/es not_active Expired
- 1975-03-25 BE BE154710A patent/BE827123A/xx unknown
-
1976
- 1976-03-31 US US05/672,322 patent/US4081448A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| US4081448A (en) | 1978-03-28 |
| ZA751497B (en) | 1976-02-25 |
| AR217037A1 (es) | 1980-02-29 |
| IL46848A0 (en) | 1975-05-22 |
| DE2511713B2 (de) | 1979-05-17 |
| DE2511713A1 (de) | 1975-10-09 |
| IT1049375B (it) | 1981-01-20 |
| AU7950175A (en) | 1976-09-30 |
| IL46848A (en) | 1978-07-31 |
| JPS50157526A (enExample) | 1975-12-19 |
| GB1496277A (en) | 1977-12-30 |
| BE827123A (fr) | 1975-07-16 |
| FR2304612B1 (enExample) | 1979-07-06 |
| BR7501750A (pt) | 1975-12-23 |
| FR2304612A1 (fr) | 1976-10-15 |
| CA1048033A (en) | 1979-02-06 |
| NL7503468A (nl) | 1975-09-29 |
| ES436006A1 (es) | 1977-01-01 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OI | Miscellaneous see part 1 | ||
| OI | Miscellaneous see part 1 | ||
| C3 | Grant after two publication steps (3rd publication) | ||
| 8339 | Ceased/non-payment of the annual fee |