New fluorinated derivatives as esterase inhibitors. Synthesis,hydration and crossed specificity studies

A variety of new fluorinated chemicals have been prepared for the first time and tested as inhibitors of esterases, one of the main enzymes involved in pheromone catabolism, in two economically important pests, the Egyptian armyworm Spodoptera littoralis (SL) and the Mediterranean corn borer Sesamia nonagrioides (SN). Using the respective major component of the pheromone as substrate, the K(m) and V(max) of the antennal esterase of both insects resulted to be 5.66 x 10(-4) M and 8.47 x 10(-6) Mmin(-1) for SL and 1.61 x 10(-7) M and 1.25 x 10(-7) Mmin(-1) for SN, pointing out that SN esterase has a higher affinity for its corresponding substrate than SL. In general, the trifluoromethyl ketones (TFMKs) exhibited higher inhibitory potency than the corresponding difluoromethyl ketones (DFMKs) or difluoroaldehydes (DFAs). The compounds appeared to hydrate differently in aqueous solution, the extent of hydration following the order: alpha,alpha-DFMKs相似文献   

Reduction of damage by the Mediterranean corn borer, Sesamia nonagrioides, and the European corn borer, Ostrinia nubilalis, in maize fields by a trifluoromethyl ketone pheromone analog

Large‐scale field experiments on the Mediterranean corn borer, Sesamia nonagrioides Lefèbvre (Lepidoptera: Noctuidae), were carried out in 2004–2006 on maize [Zea mays L. (Poaceae)] fields using (Z)‐11‐hexadecenyl trifluoromethyl ketone, an antagonist analog of the pheromone of this species, to evaluate a possible reduction of damage caused by this pest. The effect of the treatments on the European corn borer, Ostrinia nubilalis Hübner (Lepidoptera: Crambidae), a sympatric species, was also determined. Evaluation of the success of the experiments was assessed by counting (i) the number of males caught by pheromone traps in treated and untreated fields, (ii) the number of plants attacked by both insects in both plots, and (iii) the number of larvae present in infested plants in both fields. Effectiveness of the treatment was high for the second generation of the Mediterranean corn borer, the most harmful to the crop (86–90% reduction in the number of plants attacked and 67–98% reduction in the number of larvae per plant in treated fields in comparison to untreated fields), and moderate for the third generation (reduction of 41–71% and 33–77%, respectively). Treatments were also effective for the second generation of the European corn borer (61–75% reduction in the number of plants attacked, 58–78% reduction in the number of larvae found per plant) as well as for the third generation (69–97% and 70–98% reduction, respectively). By plotting the amount of the antagonist remaining on the dispensers after 40–45 days of exposure with time, the mean release rate of the compound was calculated to be 2.2%/day in 2004, 1.95%/day in 2005, and 2.1%/day in 2006, with 26% of the initial compound remaining after 20 days of experimentation. The emission rate appears to cover the flight of the most damaging second generation of both insects. Prospects of using trifluoromethyl ketones as new potential agents for pest control are also outlined.     

Monitoring of European corn borer with pheromone-baited traps: review of trapping system basics and remaining problems

Since the identification of female European corn borer, Ostrinia nubilalis (Hübner) pheromone, pheromone-baited traps have been regarded as a promising tool to monitor populations of this pest. This article reviews the literature produced on this topic since the 1970s. Its aim is to provide extension entomologists and other researchers with all the necessary information to establish an efficient trapping procedure for this moth. The different pheromone races of the European corn borer are described, and research results relating to the optimization of pheromone blend, pheromone bait, trap design, and trap placement are summarized followed by a state-of-the-art summary of data comparing blacklight trap and pheromone-baited trap techniques to monitor European corn borer flight. Finally, we identify the information required to definitively validate/invalidate the pheromone-baited traps as an efficient decision support tool in European corn borer control.     

Monitoring of the European corn borer (Lepidoptera: Crambidae) in central Maine

Pheromone trap types and within-field trap locations were compared for their effectiveness in monitoring the flight activity of European corn borer, Ostrinia nubilalis (Hübner), and its relationship to egg mass density and crop damage in sweet corn in central Maine from 1995 to 1996. The use of both 3:97 Z:E-11-tetradecenyl acetate and 97:3 Z:E-11 tetradecenyl acetate pheromone blends confirmed that European corn borer in central Maine is attracted to both pheromone lure types. European corn borer moths were captured predominantly with the E-lure type than with the Z-lure type in both years. The Scentry Heliothis trap was more effective than the Multi-Pher trap, but similar to the pheromone-baited water pan trap for monitoring European corn borer flights. With the Scentry Heliothis trap, the grassy border and 1st corn rows were the best locations for moth capture during the early flight period, but during the peak flight period, traps located in the middle of the field caught the most moths. Corn damage was recorded before moth captures in some sites and before egg mass counts in others, indicating poor efficacy of traps for early flights. Significant and positive correlations were found between moth captures in the midfield location and egg mass counts, and corn leaf damage, and between egg mass counts and corn leaf damage. However, low coefficients of variation suggest that pheromone trap captures were not good predictors of European corn borer leaf damage in sweet corn.     

Oriented flight responses of female Mediterranean fruit flies to calling males, odor of calling males, and a synthetic pheromone blend

Male Mediterranean fruit flies,Ceratitis capitata (Wiedemann), produce volatile chemicals thought to be attractive sex pheromones. We demonstrated for the first time that male odor elicits upwind flight and zigzagging upwind flight patterns in mature unmated females. Such flight patterns indicate the mechanisms involved in female location of the pheromone source and arrival at that source. Similar female oriented upwind flight responses occurred with a three component blend comprised of ethyl-(E)-octenoate, geranyl acetate, andE,E-alpha farnesene. These findings clarify the role of male sex pheromone in mate-location strategies in this species and provide new bioassay criteria for evaluating attraction responses to male pheromone and synthetic blends.     

Pheromone binding proteins in the European and Asian corn borers: no protein change associated with pheromone differences.

Pheromone binding proteins (PBPs) are thought to play a role in the recognition of sex pheromone in male moth antennae. By binding selectively to different components of pheromone blends, these PBPs could play a role in differentiating between structurally related compounds. In this study we have characterized the pheromone binding proteins of two pheromone strains of the European corn borer (Ostrinia nubilalis) and also the closely related Asian corn borer (O. furnacalis). We have been able to detect only one PBP gene, which encodes a mature protein that is identical in amino acid sequence in individuals from different pheromone strains and different species. This result suggests that the PBP is not detecting differences between the two isomeric compounds of the European corn borer pheromone or the difference in double bond position between the pheromone molecules of the European and Asian corn borers.     

Sex pheromone blend discrimination in two races and hybrids of the European corn borer moth, Ostrinia nubilalis

Abstract. The response specificity of males of two races, and hybrids, of the European corn borer moth, to a large series of doses/ratios of E- and Z11-14:OAc, was determined in a sustained-flight tunnel. For both races an area of peak response was determined, which included the natural ratio eliciting peak levels of source contact, and other treatments eliciting response profiles over the behavioural sequence not significantly different from the peak. Consistent with studies on other moth species response specificity was controlled by two threshold effects, one affecting locking-on to odour plumes of lower doses and off-ratios containing lower proportions of the E or Z isomer than the natural blend, and the other resulting in arrestment of upwind flight to higher doses and off-ratios containing higher proportions of the E or Z isomer man the natural blend. A comparison of the size of the areas of peak response showed that males of the univoltine Z race (UZ) using a 3:97 E:Z mix displayed greater specificity and sensitivity than did males of the bivoltine E race (BE) responding to a 99:1 E:Z pheromone mix. At doses higher than those eliciting peak response (<100 μg) response specificity was lower for both races, but especially for the BE race, with increased levels of upwind flight and source contact occurring to off-ratios. Finally, consistent with a previous behaviour/genetic study on this species, F₁ hybrid males displayed peak levels of source contact not only to their natural isomer ratio (65:35 E:Z), but also to an expanded range of doses of ratios ranging from 2% to 98% E.     

Impact of (Z)-7-dodecenol and turbulence on pheromone-mediated flight manoeuvres of male Trichoplusia ni

Abstract. Turbulence and chemical noise are two factors which may influence pheromone-mediated flight manoeuvres of a moth in natural habitats. In this study, the effects of turbulence and the behavioural antagonist (Z)-7-dodecenol on flight manoeuvres of male Trichoplusia ni (Hübner) were evaluated in a wind tunnel. Male moths increase airspeed and course angles when turbulence is increased. This leads to significant increases in the length of flight tracks, but significant reductions in the time taken to reach a pheromone source. In less disturbed pheromone plumes, distributions of course angles and track angles of male T.ni show a prominent peak centred about 0° relative to the upwind direction, indicating that moths can temporarily steer directly upwind toward a pheromone source.
When (Z)-7-dodecenol is released 10 cm upwind of a pheromone source to form an overlapping plume downwind, course angles, airspeeds and ground-speeds of male T.ni are reduced significantly compared with those in uncon-taminated pheromone plumes. This results in a longer flight time to reach a pheromone source. The decrease in flight speed would decrease the rate of contact with filaments, and thereby perhaps allow the moth to detect uncon-taminated pheromone filaments independently from filaments containing the behavioural antagonist.     

Mapping of QTL for resistance to the Mediterranean corn borer attack using the intermated B73 × Mo17 (IBM) population of maize

The Mediterranean corn borer or pink stem borer (MCB, Sesamia nonagrioides Lefebvre) causes important yield losses as a consequence of stalk tunneling and direct kernel damage. B73 and Mo17 are the source of the most commercial valuable maize inbred lines in temperate zones, while the intermated B73 × Mo17 (IBM) population is an invaluable source for QTL identification. However, no or few experiments have been carried out to detect QTL for corn borer resistance in the B73 × Mo17 population. The objective of this work was to locate QTL for resistance to stem tunneling and kernel damage by MCB in the IBM population. We detected a QTL for kernel damage at bin 8.05, although the effect was small and two QTL for stalk tunneling at bins 1.06 and 9.04 in which the additive effects were 4 cm, approximately. The two QTL detected for MCB resistance were close to other QTL consistently found for European corn borer (ECB, Ostrinia nubilalis Hübner) resistance, indicating mechanisms of resistance common to both pests or gene clusters controlling resistance to different plagues. The precise mapping achieved with the IBM population will facilitate the QTL pyramiding and the positional cloning of the detected QTL.     

Pheromone-blend discrimination by European corn borer moths with inter-race and inter-sex antennal transplants

Transplantation of larval antennal imaginal disks between the pheromone races of the European corn borer moth produced males and females of one race with male antennal phenotypes of the race using the opposite pheromone blend. All of the adults with transplanted antennal disks that exhibited a pheromone-mediated response in the flight tunnel did so with the pheromone blend of the recipient's race, even though the respective males and females possessed male antennae of the opposite race. Our results support the conclusion that male antennal response type is not a determining factor in pheromone-blend discrimination in male moths. Accepted: 13 November 1998     

Evidence of olfactory antagonistic imposition as a facilitator of evolutionary shifts in pheromone blend usage in Ostrinia spp. (Lepidoptera: Crambidae)

Olfactory receptor neuron (ORN) response was measured to assess why some males ("rare males") of the Asian corn borer (ACB), Ostrinia furnacalis, have a broad behavioral response to fly upwind to both the ACB and the European corn borer (ECB), Ostrinia nubilalis, pheromone blends. We performed single-sensillum electrophysiological recordings on ACB males that had been behaviorally assessed for upwind flight response to the ACB blend [60:40 (Z)-12-tetradecenyl acetate (Z12-14:OAc) to (E)-12-tetradecenyl acetate (E12-14:OAc)], as well as to ECB (Z-strain) and ECB (E-strain) blends [3:97 and 99:1 (Z)-11-tetradecenyl acetate (Z11-14:OAc) to (E)-11-tetradecenyl acetate (E11-14:OAc)]. Sensilla from all types of males had large- and small-spike-sized ORNs responding strongly to Z12- or E12-14:OAc, but weakly to Z11- and E11-14:OAc. In the majority of males ("normal males") that flew upwind only to the ACB blend, Z11-14:OAc elicited responses in an intermediate spike-sized ORN associated with behavioral antagonism that is mainly tuned to (Z)-9-tetradecenyl acetate (Z9-14:OAc). In the rare-type ACB males that flew to both the ACB and ECB pheromone blends, Z11-14:OAc did not stimulate this ORN. Increased responsiveness to ancestral pheromone components by ORNs associated with behavioral antagonism could be instrumental in reproductive character displacement, or in reinforcement and reproductive isolation during speciation by helping to increase assortative mating between males and females in derived populations that use novel sex pheromone blends.     

Olfactory neuron responsiveness and pheromone blend preference in hybrids between Ostrinia furnacalis and Ostrinia nubilalis (Lepidoptera: Crambidae)

The olfactory receptor neuron (ORN) and behavioral responses of hybrids between the Asian corn borer (ACB), Ostrinia furnacalis, and the E-strain European corn borer (ECB(E)), Ostrinia nubilalis were examined and compared to the parental populations. In hybrids and both parents, the large-spike-size ORN was capable of responding to all four pheromone components of ACB and ECB, despite differences in which compounds elicited the greatest spike frequency in each population. There was a small-spiking ORN more narrowly tuned to the minor pheromone components in both ACB and ECB(E). In hybrids the homologous small-spiking ORN was tuned primarily to the ECB(E) minor pheromone component, with some responsiveness to the ACB minor component. Both species and all the hybrids had an intermediate spike-size ORN tuned primarily to their common behavioral antagonist. Dominance of responsiveness to the ECB(E) versus the ACB minor pheromone component on the small-spiking ORN may explain the greater tendency of hybrids to fly upwind to the ECB(E) pheromone blend than the ACB blend. This finding points toward a distinct evolutionary role for this ORN in allowing a pheromone shift.     

Sex pheromone of the Asian corn borer moth

By 1975, insect sex pheromones had been identified from 60 species (1) of moths (Lepidoptera), and nearly all of the 40 compounds involved had been found to be mono- or di-unsaturated C₁₀ to C₁₈ straight-chain aldehydes, alcohols, or acetates, and the sites of olefinic unsaturation were, with one exception (2), at odd-numbered positions in the carbon chain. Since that time, many more lepidopteran pheromone components have been identified, and mono-unsaturated compounds with unsaturation at even-numbered positions in the carbon chain remain extremely rare (3–6). However, in females of $\text{Ostrinia furnacalis}$ (Guenee), called the Asian corn borer, we have discovered another mono-olefinic lepidopteran sex pheromone that has the site of unsaturation at ab even carbon position. Females of this corn-pest species produce a $\text{ca}$. 1:1 geometric mixture of ($\text{Z}$)- and ($\text{E}$)- 12-tetradecen-1-o1 acetate to attract and sexually stimulate males. On the other hand, the nearest taxonomic relative (7) of the Asian corn borer, the European corn borer, $\text{Ostrinia nubilalis}$ (Hübner), uses a mixture of ($\text{Z}$)- and ($\text{E}$)-11-tetradecen-1-o1 acetate as its sex pheromone (8). Biochemical explanation of the paucity of monounsaturated moth sex pheromones with olefinic sites at even numbered carbon positions remains to be elucidated.     

Insights into genome differentiation: pheromone-binding protein variation and population history in the European corn borer (Ostrinia nubilalis)

Examination of sequence variation at nuclear loci can give insights into population history and gene flow that cannot be derived from other commonly used molecular markers, such as allozymes. Here, we report on sequence variation at a single nuclear locus, the pheromone-binding protein (PBP) locus, in the European corn borer (Ostrinia nubilalis). The European corn borer has been divided into three races in New York State on the basis of differences in pheromone communication and life history. Previous allozyme data have suggested that there is a small but significant amount of genetic differentiation between these races. The PBP does not appear to be involved in the pheromone differences between these races. Examination of variation at the PBP locus in the three races reveals no fixed differences between races despite high levels of polymorphism. There also appears to have been considerable recombination in the history of the pheromone-binding protein alleles. Observation of both recombination between alleles and lack of significant nucleotide or insertion/deletion divergence between races leads us to suggest that these populations are either recently diverged or have continued to exchange genetic material subsequent to divergence in pheromone communication and life history.     

Trifluoromethyl ketones as inhibitors of the processionary moth sex pheromone

Aliphatic and aromatic trifluoromethyl ketones have been evaluatedin the laboratory and in the field as inhibitors of the pheromoneresponse of the processionary moth Thaumetopoea pityocampa males.Among them, two compounds, (Z)-l, l, l-trifluoro-15-octadecen-13-yn-2-oneand (Z)-l, l, l-trifluoro-16-nonadeceo-14-yn-2-one, are closelyrelated analogs of the natural pheromone (Z)-13-hexadecen-11-ynylacetate. In the laboratory experiments, carried out by pre-exposureof males to vapors of the chemicals,     

性诱剂、赤眼蜂和化学药剂协同防治大豆食心虫的研究

【目的】本文为优化大豆食心虫Leguminirora glycinioorella(Mats.)Obraztsov生物防治策略,探究不同防治策略的最佳防治时期和最佳使用量,最终达到提高防治效率及保护环境的目的。【方法】选取哈尔滨和黑河两个地区进行试验,通过比较不同措施防治大豆食心虫的防治效果,以及在大豆食心虫不同发生期单独使用性诱剂和性诱剂-赤眼蜂协同防治的防治效果,寻找最佳防治方法及最佳防治时期。通过比较在不同配比下性诱剂与化学药剂(敌敌畏)协同防治效果,寻找最适配比。【结果】结果表明:(1)性诱剂-赤眼蜂协同防治效果为60.89%,明显优于单独使用性诱剂或赤眼蜂单独防治大豆食心虫。(2)性诱剂单独使用和性诱剂赤眼蜂协同防治大豆食心虫最佳防治时期都为其盛发期前5 d,防治效果最高可达62.42%和66.08%,其次是盛发期防治,盛发期后5 d防治效果最差。(3)性诱剂-化学药剂协同防治研究发现,从防治效果、经济效益、生态保护等多方面考虑,放每667 m2放1个诱捕器和3/4药量的敌敌畏熏蒸剂效果更佳,与使用化学药剂防治效果差差异不显著,并能减少农药使用量。【结论】研究结果表明,最佳生物防治策略为在大豆食心虫盛发期前5 d利用性诱剂-赤眼蜂协同防治大豆食心虫,每667 m2放1个诱捕器和3/4药量的敌敌畏熏蒸剂,可作为从化学防治向生物防治过渡的防治方法。     

No Linkage between Genes Controlling Female Pheromone Production and Male Pheromone Response in the European Corn Borer, Ostrinia Nubilalis Hubner (Lepidoptera; Pyralidae)

The E and Z pheromonal strains of the European corn borer, Ostrinia nubilalis, are characterized by female production of and male preference for opposite blends of (E)-11-and (Z)-11-tetradecenyl acetate. It is known that the pheromone production is controlled by an autosomal gene and that the males' behavior is determined by a sex-linked gene. A third gene, autosomally inherited, has been shown to determine the organization of the male pheromone receptors. In the present study the linkage relationship between the autosomal genes controlling sex pheromone production and male olfactory sensilla was investigated. A recombination experiment showed unequivocally that the genes determining the variation in pheromone production and male pheromone receptors are not closely linked and are most likely inherited independently.     

用甜玉米粒饲养二化螟实验种群

介绍一种能够继代饲养二化螟Chilo suppressalis(Walker)实验种群的天然饲料---"甜玉米粒"及相应饲养方法。结果显示,甜玉米粒和马蹄的饲养成绩皆不同程度地高于稻苗、甘蔗和田间种群。取食甜玉米粒的幼虫存活率达92.0%,显著高于其余3种天然饲料。平均蛹重为60.7mg,单雌产卵量达197.4,除性比为0.9∶1之外,其重要生物学指标和此前报道的饲养成绩最好的马蹄没有显著差异,但成本更低,且更利于清洗消毒等加工处理,因而更适于在实际生产中大量饲养二化螟实验种群。     

Discrimination by male dogwood borer, Synanthedon scitula (Lepidoptera: Sesiidae), among traps baited with commercially available pheromone lures

The response of male dogwood borer, Synanthedon scitula (Harris) (Lepidoptera: Sesiidae), to four commercially available pheromone lures and to pheromone source concentration was evaluated in field trapping studies in commercial apple orchards in Virginia and West Virginia Male peachtree borer, Synanthedon exitiosa (Say), lesser peachtree borer, Synanthedon pictipes (Grote & Robinson), and lilac borer, Podosesia syringae (Harris), were also captured in traps baited with all lures tested. Among the lures used, the Scenturion dogwood borer lure was the most attractive to and selective for dogwood borer. Male dogwood borer showed a concentration-dependent response to traps baited with different source concentrations of the pheromone from Scenturion. Chemical analyses revealed that all lures contained principally (Z,Z)-3,13-octadecadien-1-ol acetate (ODDA) but that a significantly higher percentage of (Z,E) plus (E,Z)-3,13-ODDA was present in the Scenturion lure, compared with the others. Weekly collections of fresh male and female dogwood borer pupal exuviae from April until October in 2002 and 2003 suggested that traps baited with Scenturion lures significantly underestimated the size of populations in commercial apple orchards.