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A series of routes are described for the synthesis of new potential insecticides which are symmetrical or asymmetrical similogs of 2,5-Bis (dichloropheny1)-1,3,4-oxadiazole and its precursor diacyl hydrazine. Also two new aromatic nucleophilic substitution reactions are discussed. Activated aryl halides are reacted with fluorinated alkoxide anions. In all cases, substitution of the halogen by a fluoroalkoxy group was observed, and activated aryl halides are reacted with HMPA as an N, N-dimethyl aminating agent. In all cases, substitution of the halogen by a dimethyl amino group was observed. The effect of the activating group and the leaving group is described and a possible mechanism is proposed. All compounds synthesized are characterized and identifies by NMR, IR and /or mass spectroscopy.

This report discusses the research conducted in two areas: the synthesis of potential insecticides and the investigation of vinamidinium and azavinamidinium salt chemistry. Firstly, four classes of compounds were synthesized and characterized in the investigation of new potential insecticides. These classes of compounds include a-formamidine methyl esters, amidines, diacylhydrazines and 2,5-disubstituted-1,3,4-oxadiazoles and were characterized via NMR and infrared spectroscopy. This account also reveals and discusses the experimental conditions and procedures necessary for the preparation of these potential insecticides. Secondly, the reaction of [ 3-(dimethyl amino)-2-azaprop-2-en-1-ylidene] dimethyl ammonium chloride (Gold's Reagent) with nucleophiles such as activated (nitro) methylene compounds was examined in hopes of obtaining a more economical process for the production of indoles. Optimum reaction conditions were determined to an extent with regard to solvent, base and temperature. In addition, the reduction of vinamidinium salts was examined using numerous reducing agents; however, only sodium borohydride and sodium cyanoborohydride were found to yield unique products, that is, N,N-dimethylallylic amines and 2-aryl-3-cyanoenamines, respectively. Hence, this report also discloses the experimental conditions and procedures responsible for the novel synthesis of these products, and offers a probable mechanism for their formation. Finally, this report briefly explains the data, and offers recommendations for further research.

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The light stability of 0,0-diethyl-0-(4-ethylthiophenyl)phosphorothioate, a parent structure of a new class of fibre-reactive organophosphorus insectproofing agents for use on wool textiles was extensively examined. The rate of degradation of 0,0-diethyl-0-(4-ethylthiophenyl)phosphoro-thioate in polar and non-polar solution and on wool upon irradiation by simulated sunlight was investigated using high performance liquid chromatography.. The major photodegradation products in each case were correlated with the HPLC retention times of synthetically prepared compounds. The main product formed was the sulphoxide, 0,0-diethyl-O-(4-ethylsulphinylphenyl)phosphorothioate, whose insecticidal activity against the major textile pests was shown to be similar to that of the parent compound. In polar solution a polar product which could not be identified was formed. Both 4-ethylsulphinylphenol and 4-ethyIsulphony1-phenol were found on wool but not in solution. The effect of various ultraviolet stabilizers on the rate of photodegradation of 0,0-diethyl-0-(4-ethylthiophenyl)phosphorothioate was also examined. Ultraviolet absorbers of the 2-hydroxybenzophenone and 2-hydroxybenzotriazole classes conferred the best protection in each case. However, on wool typical wool dyes applied at conventional levels were also effective.

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