Saturated and monofluoro analogs of the oriental fruit fly attractant methyl eugenol show reduced genotoxic activities in yeast.

Methyl eugenol, is a commercially used fruit fly attractant and a suspected carcinogen. Several phenylpropenes, including methyl eugenol and the known carcinogen safrole, score negative in the Salmonella assay but score positive in the yeast DEL assay that selects for intrachromosomal recombination events in the yeast Saccharomyces cerevisiae. In an attempt to dissociate the beneficial properties of methyl eugenol from its genotoxic properties, saturated or fluorinated analogs were evaluated for their ability to induce intrachromosomal (DEL) recombination in yeast. Field tests have previously shown that all of the analogs used have appreciable properties as fruit fly attractants. The analogs 1,2-dimethoxy-4-ethylbenzene, 1,2-dimethoxy-4-(2-fluoro-2-propenyl)benzene, 1,2-dimethoxy-4-(2-fluoroethyl)benzene and 1,2-dimethoxy-4-(3-fluoro-2-propenyl)benzene all showed reduced toxicity and reduced recombinagenicity in yeast compared to methyl eugenol. These results confirm the validity of fluorination and/or removal of the 2-propenyl moiety in reducing the toxicity and recombinagenicity of methyl eugenol derivatives.

Rapid high-performance liquid chromatography method to quantitate elaterinide in juice and reconstituted residues from a bitter mutant of hawkesbury watermelon.

A C(18) reversed-phase HPLC method has been developed to analyze the concentration of 2-O-beta-D-glycopyranosyl-cucurbitacin E (synonym, elaterinide) in juice or reconstituted residues of juice derived from a bitter mutant of Hawkesbury watermelon, Citrullus lanatus (Thunb.) Matsum. & Nakai. The method requires only two steps (homogenation and filtration) for sample preparation prior to column injection and, thus, is amenable to processing large numbers of test samples. Percent elaterinide in juice samples from whole fruit, processed in various ways, ranged from 0.0230 to 0.0808%. Error differences in percent elaterinide for repetitive analyses within the same lot of juice ranged from 1.2 to 5.6%.

Substituted 2,4,6-triamino-1,3,5-thiadiazinium salts: a new heteroaromatic system.

PIP: 10 new 1,3,5-thiadiazinium iodides were synthesized, in an attempt to find insect sterilants related to hexamethylmelamine and 3,5-bis(dimethylamino)-1,2,4-ditiazolium bromide. The thiadiazinium ring was formed by reacting dithiazolium with ammonia forming amidinothiourea, then condensing it with thiophosgene. Synthesis and NMR spectra of several substituents are discussed, but no biologic tests were reported.^ieng

Susceptibility of laboratory-reared northern fowl mites, Ornithonyssus sylviarum (Acari: Macronyssidae), to selected acaricides.

Toxicity was determined for 15 acaricides against a laboratory strain of northern fowl mites, Ornithonyssus sylviarum (Canestrini and Fanzago). Adult females were exposed to residues on filter paper for 24 h. Three organophosphorous compounds (monocrotophos, cythioate, and famphur) were more toxic to the northern fowl mite than was carbaryl, the most commonly used pesticide in the poultry industry. The other tested compounds were less toxic to the mite than was carbaryl. Four of these, not used previously for northern fowl mite control, had low LC50's for northern fowl mites:aldicarb (0.46); pirimiphos-methyl (0.73); exo, exo-2,8-dichloro-4-thiatricyclo[3.2.1.0.]octane-4-oxide (AI3-63182) (0.87); and diazinon (2.48).

Attractiveness to mexican fruit flies of combinations of acetic acid with ammonium/amino attractants with emphasis on effects of hunger.

Ammonium acetate was more attractive than other ammonium salts to Mexican fruit flies (Anastrepha ludens) in an orchard test. We hypothesized that acetic acid enhanced the attractiveness of ammonia in the orchard test and that acetic acid may similarly enhance attractiveness of AMPu, an attractant consisting of a mixture of ammonium bicarbonate or ammonium carbonate, methylamine HCl, and putrescine. In laboratory experiments, acetic acid was attractive to flies deprived of either yeast hydrolysate or both sugar and yeast hydrolysate but not to flies fed both sugar and yeast hydrolysate. AMPu/acetic acid combinations were more attractive than AMPu alone to flies deprived of both sugar and yeast hydrolysate but not to flies fed sugar, regardless of yeast hydrolysate deprivation status. Acetic acid is the first attractant found that has become more attractive with both sugar and protein deprivation in studies withA. ludens. It is also the first that has enhanced the attractiveness of another attractant type. In orchard tests, yellow sticky panels baited with either AMPu or 17 mg of acetic acid were at least six times more attractive than unbaited panels. However, panels baited with both acetic acid (17-68 mg) and AMPu were less attractive than AMPu alone. These results differed from the laboratory data in which combinations were never less attractive than AMPu alone.

Isolation and identification of a compound from soybean cyst nematode,Heterodera glycines, with sex pheromone activity.

A single compound with sex pheromone activity was isolated from the female soybean cyst nematode,Heterodera glycines, by a sequence of four high-performance liquid chromatographic steps and identified as vanillic acid by a combination of ultraviolet spectroscopy and chromatography. The structure was confirmed by gas chromatography-mass spectrometry. Both attractancy and coiling behavior in male soybean cyst nematode were elicited by authentic vanillic acid.

Trans-ceralure isomers: Differences in attraction for mediterranean fruit fly,Ceratitis capitata (Wied.) (diptera: Tephritidae).

Differences in attractiveness of four individualtrans isomers of ceralure (CRL) [ethyl 4- (and 5-) iodo-trans-2-methylcyclohexane-1-carboxylate] for male Mediterranean fruit fly,Ceratitis capitata (Wiedemann), were investigated. One of the isomers, CRL-B1 (ethylcis-5-iodo-trans-2-methylcyclohexane-1-carboxylate) was significantly superior to the three othertrans-CRL isomers, CRL, trimedlure (TML) [1,1-dimethylethyl 4- (and 5-) chloro-trans-2-methylcyclohexane-1-carboxylate], and TML-C (1,1-dimethylethyl-cis-4-chloro-trans-2-methylcyclohexane-1-carboxylate) on an equal weight basis.

Synthesis of attractants for oriental fruit flyDacus dorsalis Hendel using a catalytic organocopper coupling reaction.

A general synthetic approach to various catechol derivatives was developed using a copper-catalyzed cross-coupling reaction of 1,2-dimethoxy-4-brornomethyl, 1-ethoxy-2-methoxy-4-bromomethyl- and 2-ethoxy-1-methoxy-4-bromomethylbenzenes with Grignard reagents. Dilithium tetrachlorocuprate was an acceptable catalyst in the dimethoxy series, whereas copper(I) iodide in THF-HMPA was a superior catalyst in all cases due to decreased side reactions, i.e., reduction and reductive coupling. Methyl-substituted analogs of methyl eugenol, a potent attractant of Oriental fruit fly,Dacus dorsalis Hendel, were synthesized by this method and evaluated for attractancy in field tests.

Quantitative structure-activity relationships (QSAR) of trimedlure isomers.

Trimedlure (tert-butyl 4- and 5-chloro-cis- andtrans-2-methylcyclohexane-1-carboxylate), a mixture of eight isomers, is used as an attractant for detecting and monitoring the male Mediterranean fruit fly. This paper reports the quantitative structure-activity relationship (QSAR), via CHEMX, of the eight purified isomers (racemic mixtures) of trimedlure. The relationship between structure and attractiveness is demonstrated by utilizing male medfly field catch on day 0 of the individual isomers vs. several molecular descriptors: volume, surface area, a torsion angle, and an interatomic distance.