The pyrethrins and related compounds part XL— structure-activity relationships of pyrethroidal esters with acyclic side chains in the alcohol component against resistant strains of housefly (Musca domestica)

Activities of a range of pyrethroidal esters, incorporating structural variations in all regions of the acid and alcohol components, have been measured against two fully characterised and homozygous resistant strains of Musca domestica (kdr and super-kdr). The results, limited in this paper to esters of alcohols with acyclic side chains, show the same level of uniform resistance as the kdr strain observed previously, across a range of acid and alcohol variations. Against the super-kdr strain, in contrast to the cyclic side chain set, resistance factors are barely higher than for the kdr strain. Against super-kdr flies, some dependence of resistance factor on the position of the side chain substituent was detected. Polyfluorobenzyl esters confer particularly low resistance factors.     

The microimmersion bioassay: A novel method for the topical application of pesticides to spider mites

A novel and versatile method is described for measuring the contact activity of acaricides against spider mites. The microimmersion (MI) bioassay involves drawing batches of 25 mites into small pipette tips under vacuum, immersing them for 30 s in 35 μ1 of a test solution, and then confining the treated subjects on clean foliage in holding cells. Evaluations of amitraz, bifenthrin, chlorpyrifos and dicofol against susceptible strains of Tetranychus urticae Koch showed the MI bioassay to be equally applicable to formulated and technical acaricides (the latter dissolved in acetone + distilled water; 20 + 80 by volume), and to give LC₅₀ values that corresponded well with those from a conventional residual bioassay. The most important difference between bioassay methods was the consistently greater slope of probit lines from MI tests. Results were not highly sensitive to varying the immersion period between 15 and 60 s, and low control mortality was observed with ethanol or acetone concentrations of up to 500 ml litre^?1, and surfactant concentrations of up to 10 g litre^?1. The potential of this method for assessing the relative toxicity of both fast- and slow-acting acaricides, screening small quantities of experimental compounds for acaricidal activity, and improving the laboratory procedure for selection and characterization of acaricide resistance is discussed.     

Second Oestrus Synchronization and Precocious Embryo Viability after Puberty Induction in Gilts by the Use of Gonadotrophin Treatment

The use of exogenous gonadotrophins in puberty inducement and ovulation synchronization is a technique that has a positive influence on the management of swine. The purpose of this study was to verify the effects of a second gonadotrophin treatment [equine chorionic gonadotrophin (eCG) and luteinizing hormone (LH), intramuscularly (i.m.)] upon the second oestrus synchronization and fertility in gilts. Seventy-one NAIMA (Pen Ar Lan) gilts had their first oestrus (puberty inducement) induced by a hormonal treatment (eCG and LH). Then, they were randomly distributed into two treatments, with (T1) and without (C) gonadotrophin treatment at the second oestrus. The animals were fed with a single ration (16% of crude protein and 3286.73 kcal ME/kg), and timed artificial insemination performed at the second oestrus. Gilts were slaughtered for embryo recovery and ovary examination about 5 days after insemination. There was no evidence of a difference in the percentage of the second oestrus expression (T1 - 90.90% and C - 86.84%), the duration of the oestrus cycle (T1 - 19.62 +/- 0.82 days and C - 19.67 +/- 4.14 days), the percentage of follicular cysts (T1 - 15.15% and C - 18.42%) and number of ovulations (T1 - 14.60 +/- 5.7 and C - 13.23 +/- 4.8) between treatments (p > 0.05). However, the hormonal treatment (T1) showed minor oestrus dispersion and embryo viability (T1 - 8.4 +/- 5.6 and C - 11.2 +/- 4.6) (p < 0.05). These results indicate that the better synchronization and expression of the second oestrus when using gonadotrophins (eCG and LH) is followed by a lower embryo viability, which is probably the consequence of the heterogeneous follicle recruitment during the injection of eCG.     

Synthesis and insecticidal activity of lipophilic amides. Part 4: The effect of substituents on the phenyl group of 6-phenylhexa-2,4-dienamides

Substituted phenylacetaldehydes, made by homologation of the benzaldehydes by Wittig condensation with a methoxymethylene ylid, were condensed under Wadsworth-Emmons conditions to give the substituted N-(2-methylpropyl)-6-phenylhexa-2,4-dienamides. Electron withdrawing substituents favoured the formation of the unwanted 3,5-diene isomer. Insecticidal activity was lowered by most substituents examined, but was retained or even enhanced by halogen atoms at the m- or p-positions. At the m-position, activity decreased as size of halogen increased.     

The pyrethrins and related compounds. Part XLII:Structure–activity relationships in fluoro-olefin non-ester pyrethroids

A series of compounds containing fluorine atoms in place of hydrogen in olefinic non-ester pyrethroids has been synthesised using a route based on novel intermediates, ie 2-fluoroallyl acetates, which are coupled with aryl Grignard reagents, and tested against several insect species. In most cases, after introduction of fluorine at the olefinic position, the activity remains high in both the 1-aryl-1-(3-arylprop-2-enyl)cyclopropane and the (1-aryl-4-arylbut-2-enyl)cyclopropane series. In particular, the former series have potential as soil insecticides, because in tests against Diabrotica balteata, activities were high, and dose-transferability factors were increased by the introduction of fluorine. © 1999 Society of Chemical Industry     

Milk Progesterone Profile at and after Artificial Insemination in Repeat-Breeding Cows: Effects on Conception Rate and Embryonic Death

The aim of this study was to investigate whether the skim milk progesterone concentrations at artificial insemination (AI) and day of rise of post-ovulatory progesterone concentration thereafter affect the conception and embryonic death rates in repeat-breeding cows. Milk samples were obtained from 96 repeat-breeding cows that failed to conceive to three or more AIs. The samples were taken from the cows at the day of AI and three times/week until day 45 post-AI. Skim milk was obtained after centrifugation and used for progesterone assay. The cows with a progesterone concentration more than 0.5 ng/ml at AI showed a significantly higher incidence of late embryonic death than those having a progesterone concentration<0.5 ng/ml at AI (p<0.01). As the progesterone level at insemination rose, conception rate declined. A negative correlation was shown between conception rate and skim milk progesterone level at AI. Of 56 cows showing a rise of progesterone to 1 ng/ml or more within 6 days after AI, 28 cows (50%) conceived. On the contrary, only eight of 39 cows (20.5%) conceived when the progesterone rose up to 1 ng/ml after day 6 post-AI. We concluded that increased progesterone concentration at the time of AI and delayed rise of progesterone post-AI might lead to decrease in fertility in repeat-breeding cows.     

Pathological Conditions of the Reproductive Organs of Male Stray Dogs in the Tropics: Prevalence, Risk Factors, Morphological Findings and Testosterone Concentrations

The objective of this study was to estimate the prevalence of and risk factors for pathological conditions of the reproductive organs in stray dogs under tropical conditions. Three hundred and eighteen dogs were examined post-mortem in the period from 1 July 2002 to 30 June 2003. Before killing, a blood sample (from the cephalic vein) for testosterone assay was taken. Pathological conditions of the reproductive organs were found in 135 of the dogs (42.5%) and in 175 of the testes (64.8%). The most frequent pathologies found were testicular degeneration, cryptorchidism, testicular hypoplasia and testicular tumours (in 15.1%, 6.6%, 6.6% and 5.4% of the dogs and 15.1, 4.6, 6.0 and 3.5 of the testes, respectively). Transmissible venereal tumour (TVT) was seen in 5.4% of the dogs. Testicular degeneration was more common in old dogs and underweight dogs (p < 0.05). Testicular tumours were 14.3 times more common in cryptorchid dogs. Age was another important factor for the development of testicular tumours (p < 0.05). Lower levels of testosterone concentration (p < 0.05) were observed in dogs with advanced testicular degeneration (0.7 +/- 0.8 nM), dogs with hypoplastic testicles (0.8 +/- 0.9 nM) and dogs with one degenerated and one retained testis or with bilateral cryptorchidism (1.2 +/- 0.9 nM) compared to dogs with one or two normal testes (7.0 +/- 5.5 nM). Testicular volume and weight were significantly lower in degenerated, hypoplastic and retained testes compared with the contralateral normal testis. Some spermatogenic activity was found in three of the retained testes, producing oligozoospermic smears with a high percentage of sperm abnormalities. No comparable epidemiological data about male pathological conditions of the reproductive organs in the dog is available. The prevalence found in this study, yet, appears high.     

Insecticidal activity of the pyrethrins and related compounds. VII. Insecticidal dihalovinyl analogues of cis and trans chrysanthemates

Eighteen esters of resolved cis- and trans-3-(2,2-difluoro, -dichloro or -dibromovinyl)-2,2-dimethylcyclopropanecarboxylic acids with 5-benzyl-3-furylmethyl, 3-phenoxybenzyl and α-cyano-3-phenoxybenzyl alcohols were prepared and evaluated for insecticidal activity against Musca domestica L. and Phaedon cochleariae Fab. Chlorine and bromine substituted esters are more active, in general, than those with fluorine, and in the most active esters, the cis isomer is more effective than the trans.     

Changes in cross-resistance patterns of houseflies selected with natural pyrethrins or resmethrin (5-benzyl-3-furylmethyl (±)-cis-trans-chrysanthemate)

A pyrethrins-resistant strain of houseflies, 213ab, previously selected with a 1:10 (by wt.) mixture of natural pyrethrins and piperonyl butoxide, was further selected either with natural pyrethrins alone (strain NPR) or with resmethrin (strain 104). After 50 generations the two populations differed in their resistance to the natural and synthetic esters. Both were resistant to all pyrethroids. Part of strain NPR was immune and very much more resistant than strain 104 to the natural pyrethrins and allethrin, but it was only 2–3 times more resistant than strain 104 against the new synthetic esters resmethrin (5-benzyl-3-furylmethyl (±)-cis-trans-chrysanthemate), bio-resmethrin (5-benzyl-3-furylmethyl (+)-trans-chrysanthemate), pyresmethrin (5-benzyl-3-furylmethyl pyrethrate) and 5B2Me3FC (5-benzyl-2-methyl-3-furylmethyl (±)-cis-trans-chrysanthemate). Pretreatment of both strains with sesamex diminished but did not eliminate resistance. Synergism was greater in strain NPR, especially with natural pyrethrins and allethrin. Both strains had great resistance to DDT indicating that resistance to DDT and pyrethroids is linked. Differences in resistance to different compounds suggest that at least three factors can confer resistance, one of which, pen, delays penetration and two others involve detoxication, one py a on the acid side of the ester linkage and the other, py b, on the alcohol side. Natural pyrethrins and resmethrin select for different groupings of these factors. Treatment with resmethrin does not select for py b presumably because this mechanism cannot attack the resmethrin molecule. Similarly when piperonyl butoxide is added to the natural pyrethrins py b is inhibited and so removed from selection pressure. Under these conditions, the strain produced contains the same factors as one selected by resmethrin and so shows the same small resistance to natural pyrethrins alone.     

Genetics of resistance of pyrethroid-selected houseflies,Musca domestica L.

Four resistance factors were isolated genetically from the NPR strain of houseflies (Musca domestica L.), which resists natural pyrethrins, and were characterised toxicologically. The four factors were : pen, which reduces the rate of penetration of insecticides through the cuticle; kdr-NPR, a general pyrethroid resistance mechanism unaffected by the synergist sesamex; py-ses, a mechanism of resistance to natural pyrethrins that can be suppressed by sesamex; and py-ex, a factor that gives strong resistance to synergised natural pyrethrins and to the new synthetic esters, e.g. resmethrin, but little or none to natural pyrethrins alone.