Norman F. Janes

Agropine, a new amino acid derivative from crown gall tumours

Abstract Agropine, an unusual compound produced in plant tumours was shown by mass spectrometry and proton and carbon-13 nmr spectroscopy to be a bicyclic derivative of glutamic acid and a hexitol sugar.

The pyrethrins and related compounds. Part XVIII. Insecticidal 2,2-dimethylcyclopropanecarboxylates with new unsaturated 3-substituents

Fifty new esters related to the insecticide bioresmethrin [5-benzyl-3-furylmethyl (1R,3R)-2,2-dimethyl-3-(2-methylprop-1-enyl) cyclopropanecarboxylate], having various groups in place of the 2-methylprop-1-enyl side chain, have been synthesised. cis- and trans-3-Formyl-2,2-dimethylcyclopropanecarboxylic esters are obtained by ozonolysis of the corresponding chrysanthemates. Wittig and other reactions with these esters then give the required products. 5-Benzyl-3-furylmethyl esters are obtained by transesterification or via acids obtained by cleavage of t-butyl esters under mild conditions.

An isomer of hydroxydiazinon formed by metabolism in sheep.

Four sheep were dosed with diazinon (800 or iO00 mg/kg) by stomach tube. One was killed after 48 hours and its tissues extracted with acetone. Urine was collected from the others for 3 days after dosing and extracted with ethanol-free chloroform. The tissue extract, purified by column chromatography and tic as described previously (2), except that elution of the column was continued with I:I acetone-chloroform to desorb the new metabolite, gave a sample of (Ic) which was still impure. The metabolite (Ic) was also recovered from the urine extract (after drying) by adsorption on a column of silica gel (Brockman grade II) and elution with 1:40 methanol-chloroform. Repeated tic with 1:4 acetone-hexane and 2:3 ethyl acetate-hexane gave a product pure enough for spectroscopic identification.

The pyrethrins and related compounds. Part 21. Carbon-13 nuclear magnetic resonance spectra of synthetic pyrethroids

The 13C n.m.r. spectra of a range of synthetic pyrethroids are assigned. Spectra of esters are generally similar to the combined spectra of the component acids and alcohols, and shifts show consistent trends with changes in substituent and stereochemistry, modified in some cases by small through-space effects between distant groups.