FR2351944A1 - 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
- FR2351944A1 FR2351944A1 FR7639509A FR7639509A FR2351944A1 FR 2351944 A1 FR2351944 A1 FR 2351944A1 FR 7639509 A FR7639509 A FR 7639509A FR 7639509 A FR7639509 A FR 7639509A FR 2351944 A1 FR2351944 A1 FR 2351944A1
- 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.)
- Withdrawn
Links
- 239000002917 insecticide Substances 0.000 title abstract 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 title 1
- 229910052799 carbon Inorganic materials 0.000 title 1
- YMGUBTXCNDTFJI-UHFFFAOYSA-M cyclopropanecarboxylate Chemical compound [O-]C(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-M 0.000 title 1
- 238000006704 dehydrohalogenation reaction Methods 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 abstract 6
- -1 phenoxy, benzyl Chemical group 0.000 abstract 3
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 2
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 abstract 1
- 125000002947 alkylene group Chemical group 0.000 abstract 1
- 125000003368 amide group Chemical group 0.000 abstract 1
- 125000003435 aroyl group Chemical group 0.000 abstract 1
- 125000001589 carboacyl group Chemical group 0.000 abstract 1
- YMGUBTXCNDTFJI-UHFFFAOYSA-N cyclopropanecarboxylic acid Chemical class OC(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-N 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 125000005678 ethenylene group Chemical group [H]C([*:1])=C([H])[*:2] 0.000 abstract 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- 125000001475 halogen functional group Chemical group 0.000 abstract 1
- 239000000543 intermediate Substances 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 150000002905 orthoesters Chemical class 0.000 abstract 1
- 238000005809 transesterification reaction Methods 0.000 abstract 1
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 |
|---|---|---|---|
| JP50021857A JPS5198248A (en) | 1975-02-24 | 1975-02-24 | |
| JP50028606A JPS5817451B2 (en) | 1975-03-11 | 1975-03-11 | Production method of γ↓-chloro↓-δ↓-unsaturated carboxylic acid ester |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| FR2351944A1 true FR2351944A1 (en) | 1977-12-16 |
Family
ID=26358980
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR7639509A Withdrawn FR2351944A1 (en) | 1975-02-24 | 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) | FR2351944A1 (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 FR7639509A patent/FR2351944A1/en not_active Withdrawn
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 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| ST | Notification of lapse |