Novel-Z-2-Acylamino-3-monosubstituted propenic acids and their esters and salts of the formula
 wherein R, is, by preference, hydrogen, lower alkyl or a pharmaceutically acceptable cation, R 2 is, by preference, methyl substituted cyclopropyl, (cycloalkyl)alkyl, straight alkyl with more than 4 C-atoms or ramified alkyl and R 3 is, by preference, optionally substituted alkyl, are prepared by reacting compounds of the formula
 with compounds of the formula
 or by acylation of esters of the formula
 with an acid chloride
 and treating the obtained acylated esters to the formula
 with t-butylhypochlorite and sodium methoxide, followed by treatment of the resultant intermediate with anhydrous hydrochloric acid. The novel compounds selectively inhibit the metabolism of dipeptidase (E.C.3.4.13.11) and therefore are useful in combination with antibacterial products, by preference with the thienamycin class of compounds.

Novel Z-2-acylamino-3-monosubstituted propenic acids and their esters and salts, and processes for preparing them

A method for the optical purification of an optically active 2,2-dimethylcyclopropanecarboxamide, a very useful compound as an intermediate for dehydropeptidase I inhibitor, comprises dissolving an optically active mixture of 2,2-dimethylcyclopropanecarboxamide in which either one of the optically active isomers is present in excess, in a solvent with heating, cooling the solution to deposit the racemate, filtering off the racemate and then recovering said optically active isomer from the filtrate. The amount of the solvent used is in the range of from 0.75 to 1.3 times as much as that required for the excess optically active isomer present in said optically active mixture to form a saturated solution at. a temperature at which the racemate crystal is filtered off.

A method for the optical purification of an optically active 2,2-dimethylcyclopropanecarboxylic acid amide

Industrial production of S-2,2-dimethylcyclopropanecarboxamide with a novel recombinant R-amidase from Delftia tsuruhatensis

The enantiomers of 2,2-dimethylcyclopropanecarboxylic acid are separated by salt formation with optically active 1-(3-methoxyphenyl)-ethylamine, fractional crystallization of the diastereomeric salts and subsequent decomposition of the salts with a strong acid.

Process for resolution of racemates of 2,2-dimethylcyclopropanecarboxylic acid

An ester obtained from 2,2-dimethylcyclopropanecarboxylic acid and optically active menthol, represented by the formula, ##STR1## is effectively resolved into diastereomers, which upon hydrolysis give optically active 2,2-dimethylcyclopropanecarboxylic acid Unnecessary diastereomeric ester, remained after resolution, can be epimerized selectively on the acid moiety Combination of the resolution and the epimerization provides an efficient method for production of optically active 2,2-dimethylcyclopropanecarboxylic acid

Menthyl 2,2-dimethylcyclopropanecarboxylate and resolution of the same

1,260,847. Insecticides containing cyclopropane carboxylates. NATIONAL RESEARCH DEVELOPMENT CORP. 2 Dec., 1969 [6 Dec., 1968], No. 58144/68. Heading A5E. [Also in Division C2] An insecticidal composition contains as active ingredient a furylmethyl dialkyl-cyclopropane carboxylate of the formula (I):- wherein one of R 1 and R 2 is a C 1-4 alkyl group and the other is a hydrogen atom, each of R 3 and R 4 is a hydrogen atom or an alkyl, alkenyl or alkadienyl group and Y is an alkyl, alkenyl or alkadienyl group or an aryl or heterocyclic group optionally substituted by an alkyl, alkadienyl, alkenyl or alkoxy group or by halogen atoms. The composition may be in the form of a dust, granular solid, wettable powder, emulsion, emulsifiable concentrate, spray or aerosol or other solid or liquid preparation and may also contain a pyrethrum synergist, e.g. piperonyl butoxide. The active ingredient may be used in admixture with a synthetic pyrethroid having a greater toxicity to houseflies, e.g. furylmethyl esters with chrysanthemumic or pyrethric acids, and these mixtures may be obtained by esterifying a furylmethyl alcohol with a mixture of acids or their derivatives.

Esters of cyclopropane carboxylic acids

Process for preparing pesticidal compounds

Pesticidal propenyl-cyclopropane derivatives

Compounds of the formula (I) which contain between 10 and 27 carbon atoms, and wherein m and n are independently selected from 0, 1 and 2; R is hydrogen, methyl, or ethyl; R is acetylene or contains between 3 and 18 carbon atoms and is a group R , wherein R is a C1-13 non-aromatic hydrocarbyl group, optionally substituted by a cyano or C1-4 carbalkoxy group and/or by one or two hydroxy groups and/or by one to five halo atoms which are the same or different and/or by one to three groups R which are the same or different and each contain one to four hetero atoms, which are the same or different and are chosen from oxygen, sulphur, nitrogen and silicon, 1 to 10 carbon atoms and optionally 1 to 6 fluoro or chloro atoms or R is a 6-membered aromatic ring substituted by cyano and/or by one to three groups R and/or by a group -C IDENTICAL CH, -C IDENTICAL C-R or C IDENTICAL C-halo and/or by one to five halo atoms and/or by one to three C1-4 haloalkyl groups wherein R and R are as hereinbefore defined; R and R are the same or different and are chosen from hydrogen, methyl, trifluoromethyl or cyano; and R is hydrogen or methyl provided that R is not propyl or butyl are described which have pesticidal activity, particularly against arthropod pests. Pesticidal formulations containing the compounds of the formula (I), their use in the control of pests and method for their preparation are also disclosed.

5-t-butyl-1,3-dithiane derivatives

Pesticidal compounds of formula I R.sub.A CR.sub.3 ═CR.sub.4 CHDR.sub.B I in which formula: R A represents a group ArCR 1 R 2 --in which Ar represents a phenyl or naphthyl group optionally substituted by one or more halogen, alkoxy, haloalkoxy, methylenedioxy, C 1 -C 6 alkyl or haloalkyl groups; R 1 and R 2 together with the carbon to which they are attached represent a C 3 -C 6 cycloalkyl group optionally substituted by one or more halogen atoms or C 1 -C 6 alkyl groups. R 3 and R 4 which may be identical or differ, represent hydrogen halogen or C 1 -C 6 alkyl groups and R B represents the residue of an alcohol R B CHDOH in which D is hydrogen or cyano and of which the [1R, cis]2,2-dimethyl-3-(2,2-dibromovinyl) cyclopropane carboxylic ester is significantly insecticidal, the configuration of R A and CHDR B about the double bond being mutually trans, and processes for the production of compounds I, intermediates, pesticidal compositions comprising I, processes for the production thereof, methods for controlling pests, especially rice pests, in which such compounds are utilized and the use of compounds I for the manufacture of a pesticide.

Elliott Michael

Papers

Esters of cyclopropane carboxylic acids

Process for preparing pesticidal compounds

Pesticidal propenyl-cyclopropane derivatives

5-t-butyl-1,3-dithiane derivatives

Phenyl phenoxyphenyl propenyl cyclopropane pesticides