FR2351943A1 - 2-(Dihalovinyl) cyclopropane carboxylate insecticides prodn. - by reacting alkenol and orthoformate, addition of carbon tetrahalide, basic cyclisation and dehydrohalogenation - Google Patents
2-(Dihalovinyl) cyclopropane carboxylate insecticides prodn. - by reacting alkenol and orthoformate, addition of carbon tetrahalide, basic cyclisation and dehydrohalogenationInfo
- Publication number
- FR2351943A1 FR2351943A1 FR7639508A FR7639508A FR2351943A1 FR 2351943 A1 FR2351943 A1 FR 2351943A1 FR 7639508 A FR7639508 A FR 7639508A FR 7639508 A FR7639508 A FR 7639508A FR 2351943 A1 FR2351943 A1 FR 2351943A1
- Authority
- FR
- France
- Prior art keywords
- lower alkyl
- insecticides
- reacting
- addition
- dihalovinyl
- 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.)
- Granted
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/32—Compounds having groups or 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
- C07C43/14—Unsaturated ethers
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/03—Preparation of carboxylic acid esters by reacting an ester group with a hydroxy group
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/27—Preparation of carboxylic acid esters from ortho-esters
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
- C07C67/317—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by splitting-off hydrogen or functional groups; by hydrogenolysis of functional groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
- C07C67/333—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton
- C07C67/343—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/62—Halogen-containing esters
- C07C69/65—Halogen-containing esters of unsaturated acids
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Cyclopropanecarboxylates of formula (I), are prepd. by reacting alkenols (II) with orthoesters (III) to give unsatd. esters, (IV), which, opt. after transesterification to (V), are subjected to CX4 addition to give (VI) and these dehydrohalogenated with base. (R is R1 or R8; R1 is lower alkyl; R2 and R3 are H, lower alkyl or cycloalkyl, phenyl or aralkyl; or R2 and R3 are together 2C alkylene or where one of them is not H the other can be lower alkoxycarbonyl or alkanoyl, aroyl, di (lower alkyl)amido or CN; R7 is H, lower alkyl ro cycloalkyl, phenyl or aralkyl; R8 is a gp. of formula (VII) R9 is H or CN; R10 is H, lower alkyl, phenoxy, benzyl or phenylmercapto; R11 is H or lower alkyl; R12 is O, S or vinylene; X is halo). The final stage proceeds via intermediates X, Y and Z which give (I) on further loss of HX (I) have insecticides and are prepd. more easily and in higher yields than by known processes. The prod. contain 50-90% of the more active trans isomers. Specif. claimed are (I) where X is Cl, R2 and R3 are CH3 and R is ethyl or 3-phenoxybenzyl.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP13663174A JPS5165734A (en) | 1974-11-30 | 1974-11-30 | SHIKUROPUROPANKARUBONSANESUTERUO SEIZOSURU HOHO |
JP50028606A JPS5817451B2 (en) | 1975-03-11 | 1975-03-11 | Production method of γ↓-chloro↓-δ↓-unsaturated carboxylic acid ester |
Publications (2)
Publication Number | Publication Date |
---|---|
FR2351943A1 true FR2351943A1 (en) | 1977-12-16 |
FR2351943B1 FR2351943B1 (en) | 1979-07-20 |
Family
ID=26366748
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
FR7639508A Granted FR2351943A1 (en) | 1974-11-30 | 1976-12-29 | 2-(Dihalovinyl) cyclopropane carboxylate insecticides prodn. - by reacting alkenol and orthoformate, addition of carbon tetrahalide, basic cyclisation and dehydrohalogenation |
Country Status (1)
Country | Link |
---|---|
FR (1) | FR2351943A1 (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2341553A1 (en) * | 1976-02-19 | 1977-09-16 | Bayer Ag | PROCESS FOR THE PRODUCTION OF 2,2-DIMETHYL-3- (2 ', 2'-DICHLOROVINYL) -CYCLOPROPANE-1-CARBOXYLIC ACID |
-
1976
- 1976-12-29 FR FR7639508A patent/FR2351943A1/en active Granted
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2341553A1 (en) * | 1976-02-19 | 1977-09-16 | Bayer Ag | PROCESS FOR THE PRODUCTION OF 2,2-DIMETHYL-3- (2 ', 2'-DICHLOROVINYL) -CYCLOPROPANE-1-CARBOXYLIC ACID |
Also Published As
Publication number | Publication date |
---|---|
FR2351943B1 (en) | 1979-07-20 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
GB1367207A (en) | Polyacrylates of n-hetercyclic componds,processes for their manu facture and use | |
YU197389A (en) | Process for preparing 7-substituted-hept-6-enoic and heptanoic acids and their derivatives and intermediates | |
FR2351946A1 (en) | 2-(Dihalovinyl) cyclopropane carboxylate insecticides prodn. - by reacting alkenol and orthoformate, addition of carbon tetrahalide, basic cyclisation and dehydrohalogenation | |
FR2351943A1 (en) | 2-(Dihalovinyl) cyclopropane carboxylate insecticides prodn. - by reacting alkenol and orthoformate, addition of carbon tetrahalide, basic cyclisation and dehydrohalogenation | |
FR2351944A1 (en) | 2-(Dihalovinyl) cyclopropane carboxylate insecticides prodn. - by reacting alkenol and orthoformate, addition of carbon tetrahalide, basic cyclisation and dehydrohalogenation | |
GB1409323A (en) | Process for the manufacture of oxo compounds | |
ES338638A1 (en) | New substituted phenylacetic esters, their production and compositions containing them | |
GB1437662A (en) | Cholenic acid derivative | |
GB1066117A (en) | Process for the manufacture of cyanoacetic acid esters | |
GB928157A (en) | Polymers having a high regularity of structure, obtained from esters containing a non-terminal double bond and process for preparing same | |
FR2302992A1 (en) | Prepn. of individual farnesylacetic acid (esters) geometric isomers - by rectification of isomer mixts. obtd. from nerolidol | |
GB1269400A (en) | alpha-IMIDOACRYLATES HAVING INSECTICIDAL ACTIVITY | |
ES8107150A1 (en) | Fluoro-substituted oxyalkenyl-cyclopropane-carboxylic acid esters, process for their production, intermediates therefor, their production, insecticides and acaricides that contain the final products, their preparation and use. | |
ES451982A1 (en) | Antibacterial 3-phosphono penams | |
GB1063444A (en) | Carboxyalkylmercaptomethyl siloxanes and their production | |
ES8203821A1 (en) | 3-(Chloro-3,3,4,4,4-pentafluoro-1-butenyl)-2,2-dimethylcyclopropanecarboxylic acid esters, process for their preparation and their use in insecticides. | |
GB831837A (en) | New esters of hyponitrous acid and their preparation | |
ES336700A1 (en) | 1-(alpha-methoxycyclopentoxy) methyl-2-methyl-3-ethyl-4-phenyl-4-cyclohexene | |
ES372066A1 (en) | Process for preparing substituted lactones | |
FR2202072A1 (en) | Benzophenone ether derivs - useful as pesticides | |
GB1361685A (en) | N- 1-alken-1-yl- casbamyl chlorides and their production | |
GB1296088A (en) | ||
GB1443992A (en) | Process for the manufacture of polyene compounds | |
GB1000522A (en) | Novel esters and their use as perfumery components | |
Nazarov et al. | Structural orientation in the diene condensations of 2-alkyl-1, 3-butadienes with unsymmetrical dienophiles |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
ST | Notification of lapse |