59609-49-3

Usage

Uses

Used in Agricultural Industry:
Ethyl 3-(2,2-dichlorovinyl)-2,2-dimethyl-1-cyclopropanecarboxylate is used as an insecticide for protecting crops from damage caused by various pests, including insects and mites. Its strong insecticidal properties make it an effective solution in controlling these agricultural threats.

InChI:InChI=1/C10H14Cl2O2/c1-4-14-9(13)8-6(5-7(11)12)10(8,2)3/h5-6,8H,4H2,1-3H3

Upstream product

• 623-73-4 diazoacetic acid ethyl ester 
• 55667-43-1 1,1-dichloro-4-methyl-penta-1,3-diene 
• 72800-48-7 1,1,1-trichloro-4-methyl-3-penten-2-ol 
• 107-86-8 3,3-dimethyl acrylaldehyde 
• 866-23-9 diethyl (trichloromethyl)phosphonate 
• 66692-75-9 ethyl 3-formyl-2,2-dimethylcyclopropanecarboxylate 
• 1608-26-0 Hexamethylphosphorous triamide 
• 3167-62-2 diethyl (dichloromethyl)phosphonate 
• 865-47-4 potassium tert-butylate 
• 66395-60-6 2,2-dimethyl-3-(β,β-dichlorovinyl)-cyclobutanone 
• 55701-05-8 3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylic acid 
• 59609-50-6 ethyl 2-(2,2-dichlorovinyl)-3,3-dimethyl-1-ethoxycarbonylcyclopropanecarboxylate 
• 67-68-5 dimethyl sulfoxide 
• 65771-92-8 3-methyl-3-chloro-2-(2',2'-dichlorovinyl)-butanecarboxylic acid ethyl ester 

Downstream Products

• 55667-40-8 trans-permethrin acid 
• 59042-49-8 cis-permethrinic acid 
• 52314-67-7 permethric acid chloride 
• 55701-05-8 3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylic acid 

Relevant academic research and scientific papers

ASYMMETRIC SYNTHESIS OF CYCLOPROPANE CARBOXYLATES: CATALYSIS OF DIAZOACETATE REACTIONS BY COPPER(II) SCHIFF BASE COMPLEXES DERIVED FROM α-AMINO ACIDS

The asymmetric synthesis of cyclopropane carboxylates, which are intermediates in the synthesis of photostable pyrethroid insecticides, by catalysed reaction of ethyl dizaoacetate with halo-olefins is described.Using chiral copper(II) Schiff base complexes derived from L-phenylalanine and aromatic aldehydes as catalysts, both the degree and direction of optical induction were found to depend upon the olefin.Unexpectedly, in several reactions there was marked stereoselectivity at C(3), rather than C(1), of the cyclopropanes.This novel pattern of selectivity is interpreted in terms of carbene transfer from a metal-carbene intermediate in which a chiral ligand controls the orientation of an approaching olefin.

A Practical and Efficient Synthesis of Fluorinated Pyrethroids. cis-3-(2-Chloro--3,3,3-trifluoro-1-propenyl)-2,2-dimethylcyclopropanecarboxylates

A practical and efficient route to fluorinated pyrethroids has been developed which involves the selective formation of the cis-cyclopropane ring using intramolecular alkylation of the haloaldehyde and a novel transformation of the aldehydes to the corresponding esters via the cyanohydrins.

Cyclopropanation process

A process for producing a cyclopropane derivative comprising contacting a diazo compound and an olefinically unsaturated compound in the presence of a catalytic amount of copper cation-exchanged perfluorinated ion exchange polymer is disclosed.

Process for the preparation of 1,1-dichloro-alkenes

A process for the preparation of a 1,1-dichloro-alkene of the formula STR1 in which R1 is hydrogen, or an optionally substituted alkyl, alkenyl, alkinyl, cycloalkyl, aralkyl, aralkenyl or aryl radical, and R2 is an optionally substituted alkyl, alkenyl, alkinyl, cycloalkyl, aralkyl, aralkenyl or aryl radical, or R1 and R2 together form an optionally branched and/or optionally benzo-fused hydrocarbon chain, comprising reacting a carbonyl compound of the formula STR2 with a trichloromethanephosphonic acid ester of the formula STR3 in which R3 each individually is an alkyl or phenyl radical, or together are alkanediyl, in the presence of at least an equimolar amount of magnesium. Advantageously, R1 is hydrogen, R2 is a C2 to C5 alkenyl radical or a radical of the formula STR4 Z is a cyano, acetal, carboxyl or C1 to C4 alkoxycarbonyl radical, or a radical of the formula COOM, and M is sodium or potassium, R3 each individually is a C1 to C4 alkyl or phenyl radical, or the two radicals R3 together are C2 to C5 alkanediyl, about 0.95 to 1.4 moles of the trichloromethanephosphonic acid ester and about 1.5 to 4 moles of magnesium are employed per mole of the carbonyl compound, and the reaction is carried out at a temperature between about 0° and 150° C. in a polar aprotic solvent. The products are known intermediates, especially for insecticides.

Method of producing cyclopropanecarboxylic acids and esters

Novel γ-lactone derivatives are provided. These lactone derivatives, when reacted with hydrogen halide in alcohol, yield γ-halogeno-δ-unsaturated carboxylic acid esters. This ring-opening process is useful for the purpose of increasing the yield of pyrethrin analogs which are of value as insecticides and agricultural chemicals. Thus, the γ-lactone derivatives by-produced in the production process for dihalogenovinyl chrysanthemumates are caused to undergo ring-opening reaction to yield the corresponding γ-halogeno-δ-unsaturated carboxylic acid esters which are important intermediates for said pyrethrin analogs.

Preparation of 1,1-dihalogeno-alkenes

In the preparation of a 1,1-dihalogenoalkene of the formula STR1 in which R1 is a hydrogen atom or an optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, aralkyl, aralkenyl or aryl radical, and R2 is an optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, aralkyl, aralkenyl or aryl radical, or R1 and R2 together form an optionally branched and/or optionally benzo-fused hydrocarbon chain, and X1 and X2 each independently is a halogen atom, wherein a carbonyl compound of the formula STR2 is reacted with a trihalogenoacetate of the formula STR3 in which X3 is a halogen atom, and M≈ is an alkali metal ion or one equivalent of an alkaline earth metal ion, in the presence of an approximately equimolar amount of a phosphorus-containing compound, the improvement which comprises employing as said phosphorus-containing compound a phosphorous acid trialkyl ester or a phosphorous acid triamide and effecting the reaction at a temperature between about 0° and 200° C. A preferred end product is STR4 and the preferred phosphorus-containing compound is trimethyl phosphite, triethyl phosphite, tripropyl phosphite or phosphorous acid tris-dimethyl-amide.

TRANSITION METAL CATALYZED REACTIONS OF DIAZOESTERS; CYCLOPROPANATION OF DIENES AND TRIENES

The regioselectivity of the cyclopropanation of polyenes by cycloaddition of carbenes generated by catalysed decomposition of diazoesters in the presence of Rh, Pd and Cu catalyst can be controlled to some extent by selecting proper rection parameters.For a particular diene, the regioselectivity depends both on the catalyst and on the nature of the double-bond (conjugation, substitution).The cyclopropanation of trienes containing both a conjugated diene system and an isolated double bond is reported as an application of these reactions.The practical interest of the present study is further demonstrated by the synthesis of a pyrethroid precursor by the rhodium(II) carboxylates catalyzed-cyclopropanations of 1,1-dichloro-4-methyl-1,3-pentadiene.

Process for the preparation of 1,1-dichloro-alkenes

A process for the preparation of a 1,1-dichloroalkene of the formula STR1 in which R1 is hydrogen, or an optionally substituted alkyl, alkenyl, alkinyl, cycloalkyl, aralkyl, aralkenyl or aryl radical, and R2 is an optionally substituted alkyl, alkenyl, alkinyl, cycloalkyl, aralkyl, aralkenyl or aryl radical, or R1 and R2 together form an optionally branched and/or optionally benzo-fused hydrocarbon chain, comprising reacting a carbonyl compound of the formula STR2 with a trichloromethanephosphonic acid ester of the formula STR3 in which R3 each individually is an alkyl or phenyl radical, or the two radicals R3 together are alkanediyl, in the presence of at least an equimolar amount of a phosphorous acid triamide of the formula in which R4 each independently is an alkyl radical, or the two radicals R4 together are alkanediyl. Advantageously, R1 is hydrogen, R2 a C2 to C5 alkenyl radical, or a radical of the formula STR4 Z is a cyano, acetyl, carboxyl or C1 to C4 alkoxycarbonyl radical, or a radical of the formula --COOM, M is sodium or potassium, and R3 each individually is a C1 to C4 alkyl or phenyl radical, or the two radicals R3 together are C2 to C5 alkandiyl, the phosphorous acid triamide is phosphorous acid tris-dimethylamide or tris-diethylamide, about 0.94 to 1.1 moles of each of trichloromethanephosphonic acid ester and of the phosphorous acid triamide are employed per mole of the carbonyl compound, and the reaction is effected at about 10° to 100° C. in a polar aprotic solvent.

Process for the preparation of cyclopropane carboxylic acid esters

3-(Halogenovinyl- or propenyl-)-2,2-dimethyl cyclopropane-1-carboxylic acid esters, which are precursors of, or may themselves be, pyrethroid insecticides, are prepared by the reaction of certain halogenopentadienes with an alkyl diazoacetate in the presence of a catalyst which is a transition metal complex of certain chiral Schiff bases, which catalysts tend to increase the yield of preferred cis IR isomer relative to the other possible isomers.