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Keywords = moth sex pheromones

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11 pages, 1040 KiB  
Article
A Concise Asymmetric Synthesis of Sex Pheromone of Euproctis pseudoconspersa (Strand) and Its Enantiomer
by Biyu An, Shengli Liu, Jianan Wang, Dan Liu, Qinghua Bian and Jiangchun Zhong
Molecules 2025, 30(12), 2494; https://doi.org/10.3390/molecules30122494 - 6 Jun 2025
Viewed by 464
Abstract
The tea tussock moth, Euproctis pseudoconspersa (Strand), is a serious pest, and its sex pheromone is (R)-10,14-dimethylpentadecyl isobutyrate. A new and concise asymmetric synthesis of the sex pheromone and its enantiomer was accomplished. The chiral methyl of the pheromone was introduced [...] Read more.
The tea tussock moth, Euproctis pseudoconspersa (Strand), is a serious pest, and its sex pheromone is (R)-10,14-dimethylpentadecyl isobutyrate. A new and concise asymmetric synthesis of the sex pheromone and its enantiomer was accomplished. The chiral methyl of the pheromone was introduced by Evans’s template, while the extension of the carbon chain was achieved through Li2CuCl4-catalyzed coupling of chiral tosylate with Grignard reagent. Full article
(This article belongs to the Special Issue Synthesis of Bioactive Compounds, 3rd Edition)
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31 pages, 469 KiB  
Review
What Can We Learn from Dissecting Tortricid Females About the Efficacy of Mating Disruption Programs?
by Alan Lee Knight, Michele Preti and Esteban Basoalto
Insects 2025, 16(3), 248; https://doi.org/10.3390/insects16030248 - 28 Feb 2025
Viewed by 877
Abstract
Female mating success for the tortricids codling moth (CM), Cydia pomonella, Oriental fruit moth (OFM), Grapholita molesta, European grape vine moth (EGVM), Lobesia botrana, and five leafroller (LR) species under various mating disruption (MD) programs was reviewed at a time [...] Read more.
Female mating success for the tortricids codling moth (CM), Cydia pomonella, Oriental fruit moth (OFM), Grapholita molesta, European grape vine moth (EGVM), Lobesia botrana, and five leafroller (LR) species under various mating disruption (MD) programs was reviewed at a time when new dual sex lures can provide alternative tools to assess female mating. Previous reliance on passive assessments such as tethering and virgin female-baited traps with laboratory moths are at odds with active trapping methods of wild moths. Additive factors such as delayed mating, adjustments in female behaviors, and greater levels of natural control may or may not contribute to the apparent success of MD. Current MD programs are not based solely on research, as economics and commercialization require some compromise. The complete sex pheromone blend is not always used. A delay in mating has been reported from the field with one study and suggested that reductions in fecundity would likely be minimal. There is no evidence that MD works better with low population densities. MD is an established technology, but the new dual sex lures are showing that the density of mated females is rather high. Efforts to improve the efficacy of MD are ongoing with a small cadre of researchers. Full article
15 pages, 12775 KiB  
Article
Transcriptome Profiling of Euproctis pseudoconspersa Reveals Candidate Olfactory Genes for Type III Sex Pheromone Detection
by Xiangzhi Zhang, Shunsi Li, Zongxiu Luo, Xiaoming Cai, Lei Bian, Chunli Xiu, Nanxia Fu, Naiyong Liu, Zhengqun Zhang and Zhaoqun Li
Int. J. Mol. Sci. 2025, 26(4), 1405; https://doi.org/10.3390/ijms26041405 - 7 Feb 2025
Cited by 1 | Viewed by 813
Abstract
The tea tussock moth (Euproctis pseudoconspersa) is a common tea plantation pest with Type III sex pheromone components (SPCs). However, the olfactory genes involved in the perception of Type III SPCs remain unknown. To identify the olfactory genes involved in E [...] Read more.
The tea tussock moth (Euproctis pseudoconspersa) is a common tea plantation pest with Type III sex pheromone components (SPCs). However, the olfactory genes involved in the perception of Type III SPCs remain unknown. To identify the olfactory genes involved in E. pseudoconspersa olfactory perception, we sequenced the transcriptomes of different tissues from male and female moths. We identified 27 chemosensory proteins, 39 odorant-binding proteins (OBPs), 28 ionotropic receptors (IRs), and 67 odorant receptors (ORs). Phylogenetic and antennal abundance analyses showed that EpseOR12, EpseOR13, EpseOR15, EpseOR16, and EpseOR18 belonged to the pheromone receptor clades of Type II moths, with predominant expression in male antennae. Besides these EpseORs, EpseOR14 and EpseOR32 were two of the most abundant EpseORs in male antennae, where they were predominantly expressed. Four pheromone-binding proteins (PBPs) were identified, with higher expression in male antennae. EpseORs and EpsePBPs may be involved in Type III SPC detection. Additionally, a few EpseOBPs, EpseIRs, and EpseORs were predominantly expressed in either male or female antennae. These genes may play important roles in olfaction and may be involved in detecting host plant volatiles and pheromones. These results provide a foundation for further exploration of the molecular mechanisms of E. pseudoconspersa olfaction. Full article
(This article belongs to the Section Molecular Genetics and Genomics)
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19 pages, 3989 KiB  
Article
Factors Impacting the Use of an Allelochemical Lure in Pome Fruit for Cydia pomonella (L.) Monitoring
by Alan Lee Knight, Michele Preti and Esteban Basoalto
Insects 2025, 16(2), 172; https://doi.org/10.3390/insects16020172 - 6 Feb 2025
Cited by 1 | Viewed by 914
Abstract
A four-component blend comprising pear ester, DMNT, linalool oxide, and acetic acid (CM4K) was identified as a potent allelochemical lure for both sexes of codling moth (CM), Cydia pomonella (L.). Studies conducted from 2020 to 2022 in Washington State (USA) examined factors which [...] Read more.
A four-component blend comprising pear ester, DMNT, linalool oxide, and acetic acid (CM4K) was identified as a potent allelochemical lure for both sexes of codling moth (CM), Cydia pomonella (L.). Studies conducted from 2020 to 2022 in Washington State (USA) examined factors which could impact the lure’s relative performance. The CM4K lure was effective across a range of mating disruption programs and was equally attractive in monitoring wild and sterile CM. The lure remained attractive for at least 10 weeks. Total catch in traps baited with the CM4K was significantly less impacted than a sex pheromone lure located near mating disruption dispensers and female catches were largely unaffected. Traps with the CM4K lure caught significantly more females and fewer males when placed near clusters of fruits in a trellised orchard. Two factors were found to significantly impact the relative performance of the CM4K to sex pheromone lures: the CM4K lure was only equivalent to sex pheromone lures in pear MD orchards, and apple and pear orchards with vigorous weed growth. This is the first report of a monitoring lure for a tortricid moth being negatively impacted by the background odor of non-host weed species present within an orchard. Full article
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8 pages, 1005 KiB  
Article
First Report of a Migratory Pest, the Fall Armyworm, Spodoptera frugiperda (JE Smith, 1797) (Lepidoptera, Noctuidae) from Bulgaria
by Szabolcs Szanyi, Marek Barta, Dimitar Velchev, Stoyan Beshkov, Stephen Mumford, Ivaylo Todorov, Antal Nagy, Zoltán Varga, Miklós Tóth and Teodora Toshova
Insects 2025, 16(2), 134; https://doi.org/10.3390/insects16020134 - 30 Jan 2025
Viewed by 1343
Abstract
The first occurrence of an invasive pest species, the fall armyworm (Spodoptera frugiperda, Lepidoptera: Noctuidae), in Bulgaria is reported. Different trapping methods (black light trap, traps baited with semiochemical lures, and food attractants) were used to study Noctuidae assemblages in Bulgaria in [...] Read more.
The first occurrence of an invasive pest species, the fall armyworm (Spodoptera frugiperda, Lepidoptera: Noctuidae), in Bulgaria is reported. Different trapping methods (black light trap, traps baited with semiochemical lures, and food attractants) were used to study Noctuidae assemblages in Bulgaria in 2023. Two males of S. frugiperda were caught with sex pheromone traps in maize fields in Knezha, northern Bulgaria, in early November 2023. Additionally, three moths were attracted by black light traps (early November 2023) and one moth by a food lure applied on a tree trunk at the end of October 2023 in the municipalities of Parvomay and Chirpan, southern Bulgaria, respectively. The identification of S. frugiperda was confirmed using morphological and molecular methods. Full article
(This article belongs to the Special Issue Travelers on the Wind: Migratory Insects as Emerging Research Models)
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18 pages, 7697 KiB  
Article
Tissue Expression and Characterization of Eogystia hippophaecolus (Lepidoptera: Cossidae) Odorant Receptors
by Chunyan Chen, Yiming Niu, Sainan Zhang, Sanhe Liu, Xiangbo Lin, Shixiang Zong and Jing Tao
Forests 2025, 16(1), 98; https://doi.org/10.3390/f16010098 - 9 Jan 2025
Viewed by 719
Abstract
Eogystia hippophaecolus (Hua, Chou, Fang et Chen) is a drilling pest that damages sea buckthorn, leading to substantial ecological and economic losses in areas where sea buckthorn is cultivated in China. Pheromone lures are widely used to monitor and trap male moths; however, [...] Read more.
Eogystia hippophaecolus (Hua, Chou, Fang et Chen) is a drilling pest that damages sea buckthorn, leading to substantial ecological and economic losses in areas where sea buckthorn is cultivated in China. Pheromone lures are widely used to monitor and trap male moths; however, the olfactory recognition mechanisms in male moths require further investigation. In this study, we characterized odorant receptor genes using phylogenetics, gene expression, sequence analyses and molecular docking. A phylogenetic analysis using the maximum likelihood method revealed that odorant receptor co-receptor (EhipOrco) genes clustered with other lepidopteran Orco genes, while pheromone receptor (EhipPR) genes clustered with other lepidopteran PR genes, suggesting that these genes have similar functions. The expression levels of 27 odorant receptor (EhipOR) genes in five tissues of male adults were analyzed using qPCR. Nine EhipOR genes were specifically expressed in the antennae, while several EhipOR genes were highly expressed in the head, feet, and external genitalia. As determined using molecular docking, EhipPR1–3 bound strongly to the primary sex pheromone components of E. hippophaecolus. Additionally, EhipPR1–3 demonstrated a strong binding affinity for longifolene among sea buckthorn volatiles. This study provides a foundation for future functional research on EhipORs and the olfactory recognition mechanisms of E. hippophaecolus. Full article
(This article belongs to the Section Forest Health)
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13 pages, 3185 KiB  
Article
Characterization of a Novel Male Pheromone Compound in Leucoptera sinuella (Lepidoptera: Lyonetiidae) and Its Role in Courtship Behavior
by Laura Sánchez-Aros, Abel F. O. Queiroz, Jorge Guajardo, Wilson Barros-Parada, Glenn P. Svensson and Jan Bergmann
Insects 2025, 16(1), 32; https://doi.org/10.3390/insects16010032 - 31 Dec 2024
Viewed by 923
Abstract
The poplar moth, Leucoptera sinuella (Lepidoptera: Lyonetiidae), is widely distributed across Europe, Asia, and parts of Africa. It was first identified in Chile in 2015 and has since become a significant pest in the agricultural sector. Additionally, economic losses are further aggravated by [...] Read more.
The poplar moth, Leucoptera sinuella (Lepidoptera: Lyonetiidae), is widely distributed across Europe, Asia, and parts of Africa. It was first identified in Chile in 2015 and has since become a significant pest in the agricultural sector. Additionally, economic losses are further aggravated by the presence of L. sinuella pupae in nearby fruit orchards. This study investigated the presence of a male-produced sex pheromone in L. sinuella, focusing on the hairpencil (HP) glands, which are known as dissemination structures for male pheromones in lepidopterans. Male HP glands were solvent-extracted and analyzed by gas chromatography–mass spectrometry. Chemical microderivatization and comparisons of mass spectra and retention indices of natural compounds with synthetic standards led to the identification of two compounds: (Z)-3-decenyl hexanoate (the major component) and (Z)-3-decen-1-ol (a minor component). Although electrophysiological assays did not show detectable antennal responses to (Z)-3-decenyl hexanoate, behavioral bioassays demonstrated its role as a short-range courtship signal in L. sinuella. Males with ablated hairpencils exhibited significantly reduced courtship success compared to controls; however, exposure of females to synthetic (Z)-3-decenyl hexanoate or HP extract restored male courtship success. To our knowledge, (Z)-3-decenyl hexanoate has not been previously reported as a sex pheromone component in any insect species, making this discovery an intriguing addition to the diversity of chemical communication in insects. Full article
(This article belongs to the Section Insect Pest and Vector Management)
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15 pages, 14402 KiB  
Article
Pheromone-Binding Protein 1 Performs a Dual Function for Intra- and Intersexual Signaling in a Moth
by Yidi Zhan, Jiahui Zhang, Mengxian Xu, Frederic Francis and Yong Liu
Int. J. Mol. Sci. 2024, 25(23), 13125; https://doi.org/10.3390/ijms252313125 - 6 Dec 2024
Cited by 2 | Viewed by 1016
Abstract
Moths use pheromones to ensure intraspecific communication. Nevertheless, few studies are focused on both intra- and intersexual communication based on pheromone recognition. Pheromone-binding proteins (PBPs) are generally believed pivotal for male moths in recognizing female pheromones. Our research revealed that PBP1 of Agriphila [...] Read more.
Moths use pheromones to ensure intraspecific communication. Nevertheless, few studies are focused on both intra- and intersexual communication based on pheromone recognition. Pheromone-binding proteins (PBPs) are generally believed pivotal for male moths in recognizing female pheromones. Our research revealed that PBP1 of Agriphila aeneociliella (AaenPBP1) serves a dual function in both intra- and intersexual pheromone recognition. Here, a total of 20 odorant-binding protein (OBP) family genes from A. aeneociliella were identified and subjected to transcriptional analysis. Among these, AaenPBP1 was primarily highly expressed in the antennae. Competitive fluorescence binding assays and molecular docking analyses demonstrated that AaenPBP1 exhibits a strong binding affinity for the female sex pheromone (Z)-9-Hexadecenyl acetate and the male pheromone 1-Nonanal. Notably, hydrogen bonds were observed between Ser56 and the ligands. The analysis of pheromone components and PBPs in lepidopteran lineage suggested that their strong and precise interactions, shaped by coevolution, may play a crucial role in facilitating reproductive isolation in moths. Our findings provide valuable insight into the functional significance of PBPs in invertebrates and support the development of behavioral regulation tools as part of an integrated pest management strategy targeting crambid pests. Full article
(This article belongs to the Special Issue Molecular Signalling in Multitrophic Systems Involving Arthropods)
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17 pages, 7585 KiB  
Article
The Dynamics of Pheromone Release in Two Passive Dispensers Commonly Used for Mating Disruption in the Control of Lobesia botrana and Eupoecilia ambiguella in Vineyards
by Marta Corbetta, Luca Bricchi, Vittorio Rossi and Giorgia Fedele
Insects 2024, 15(12), 962; https://doi.org/10.3390/insects15120962 - 3 Dec 2024
Cited by 1 | Viewed by 1431
Abstract
Background: Mating disruption (MD) is a worthwhile technique for the control of Lobesia botrana and Eupoecilia ambiguella in central Europe and Mediterranean areas. MD efficacy is affected by the pheromone release (PR), which in turn is influenced by environmental conditions. Methods: The effect [...] Read more.
Background: Mating disruption (MD) is a worthwhile technique for the control of Lobesia botrana and Eupoecilia ambiguella in central Europe and Mediterranean areas. MD efficacy is affected by the pheromone release (PR), which in turn is influenced by environmental conditions. Methods: The effect of weather conditions on PR was evaluated under four different fields in northern Italy. The PR of two commercial types of MD passive dispensers was correlated with different variables. Results: For both dispensers, the temperature and vapor pressure deficit explained PR in vineyards with diverse weather conditions better than time. The effect of temperature was not linear, and any temperature increase at high temperatures accelerated the PRR more than proportionally. One dispenser type showed a non-linear release trend of the pheromone emission in field conditions with respect to the considered variables; further, the stepwise regression pointed out the importance of the dichotomous variable associated with the vineyard for increasing the goodness-of-fit. Conclusions: The equations developed in this work are dispenser-dependent and can provide information on the PR during the season for each dispenser type, as influenced by weather conditions. These equations could serve as an input for a pheromone concentration model to predict concentrations based on meteorological conditions. Full article
(This article belongs to the Special Issue Advances in Chemical Ecology of Plant–Insect Interactions)
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19 pages, 6868 KiB  
Article
Functional Role of Odorant-Binding Proteins in Response to Sex Pheromone Component Z8-14:Ac in Grapholita molesta (Busck)
by Yuqing Luo, Xiulin Chen, Shiyan Xu, Boliao Li, Kun Luo and Guangwei Li
Insects 2024, 15(12), 918; https://doi.org/10.3390/insects15120918 - 25 Nov 2024
Cited by 2 | Viewed by 1072
Abstract
The plum fruit moth (PFM), Grapholita funebrana, and the oriental fruit moth (OFM), G. molesta, are closely related fruit moth species that severely damage fruit trees in Rosaceae. Both species share common primary sex pheromone components Z8-12:Ac and E8-12:Ac. The secondary [...] Read more.
The plum fruit moth (PFM), Grapholita funebrana, and the oriental fruit moth (OFM), G. molesta, are closely related fruit moth species that severely damage fruit trees in Rosaceae. Both species share common primary sex pheromone components Z8-12:Ac and E8-12:Ac. The secondary sex pheromone components of PFMs consist of Z8-12:OH, Z8-14:Ac, and Z10-14:Ac, while those of OFMs include Z8-12:OH and 12:OH. Previous researchers have proved that the inclusion of Z8-14:Ac and Z10-14:Ac did not augment PFM catches but inhibited OFM catches in orchards in Europe, thereby maintaining the species-specificity of the PFM sex attractant. However, which of these components, Z8-14:Ac or Z10-14:Ac, plays the major role in inhibiting OFM attraction remains unclear. In the current study, electroantennogram (EAG) assays indicated that both OFM and PFM males exhibited a moderate EAG response to Z8-14:Ac and Z10-14:Ac. Rubber septa loaded with varying ratios of Z8-14:Ac (1% to 30%) or Z10-14:Ac (5% to 110%) combined with a constant dose of Z8-12:Ac and E8-12:Ac produced diverse trapping effects. Sex attractants containing Z8-14:Ac did not significantly affect the trapping of PFM males but drastically reduced the capture of OFM males, with the reduction reaching up to 96.54%. Attractants containing more than 10% of Z10-14:Ac simultaneously reduced the number of OFM and PFM males captured. Z8-14:Ac was indispensable for maintaining the specificity of sex pheromones. Fluorescence competitive binding assays of recombinant GmolPBP2 showed the lowest Ki value (0.66 ± 0.02 μM) among the PBPs/GOBPs from OFMs, suggesting that it is the most likely target for Z8-14:Ac. Molecular dynamic simulation and site-directed mutagenesis assays confirmed that the Phe12 residue, which forms a π–alkyl interaction with Z8-14:Ac, was crucial for GmolPBP2 binding to Z8-14:Ac. In conclusion, Z8-14:Ac is vital to the specificity of PFM sex pheromones inhibiting OFM attractants when added to Z8-12:Ac and E8-12:Ac. This could be potentially used to develop species-specific sex attractants for the PFM. Full article
(This article belongs to the Special Issue New Advances in Insect Chemical Adaptation)
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12 pages, 2154 KiB  
Article
Attraction of the Indian Meal Moth Plodia interpunctella (Lepidoptera: Pyralidae) to Commercially Available Vegetable Oils: Implications in Integrated Pest Management
by Junyan Liu, Zhuoer Yu, Xiong Zhao He, Guoxin Zhou, Mengbo Guo and Jianyu Deng
Agriculture 2024, 14(9), 1526; https://doi.org/10.3390/agriculture14091526 - 4 Sep 2024
Cited by 1 | Viewed by 1814
Abstract
The Indian meal moth, Plodia interpunctella, poses a significant threat to global agricultural products. Although pheromone-based technologies show promise for P. interpunctella management, limitations such as single-sex targeting necessitate exploring complementary strategies. Vegetable-based oils represent a potential alternative but their efficacy, sex-specificity, [...] Read more.
The Indian meal moth, Plodia interpunctella, poses a significant threat to global agricultural products. Although pheromone-based technologies show promise for P. interpunctella management, limitations such as single-sex targeting necessitate exploring complementary strategies. Vegetable-based oils represent a potential alternative but their efficacy, sex-specificity, and interaction with sex pheromones remain unclear. To address these questions, we first examined the attraction of P. interpunctella female and male adults to 10 commercially available vegetable oils in semi-field conditions. Sesame, olive, and blended oils were the most attractive, capturing significantly more adults compared to other oils. We then evaluated the effectiveness of these three attractive oils and their combinations with P. interpunctella sex pheromones in a grain warehouse. Traps baited with these oils captured significantly more females and males compared to control traps without attractants; however, the addition of sex pheromones did not improve male capture and significantly reduced female capture, suggesting an inhibitory effect. Finally, we demonstrated that female mating status (mated vs. virgin) did not influence the attractiveness of traps baited with these effective oils. Our findings highlight the potential of standalone traps baited with blended, olive, or sesame oil as a practical, economic, and effective management strategy for P. interpunctella in storage facilities. Full article
(This article belongs to the Section Crop Protection, Diseases, Pests and Weeds)
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12 pages, 2232 KiB  
Article
Physiological Status of Rice Leaf-Roller Cnaphalocrocis medinalis (Lepidoptera: Crambidae) Adults Trapped by Sex Pheromone and Floral Odor
by Jianfei Lu, Xiaoming Yao, Ying Shen, Caroline Du, Qianshuang Guo and Yongjun Du
Insects 2024, 15(9), 637; https://doi.org/10.3390/insects15090637 - 25 Aug 2024
Viewed by 1576
Abstract
The rice leaf-roller Cnaphalocrocis medinalis is an important migratory pest of rice. We conducted a study to determine the physiological status of adults trapped by a sex pheromone and floral odor. In the immigrant group, the number of males trapped by the floral [...] Read more.
The rice leaf-roller Cnaphalocrocis medinalis is an important migratory pest of rice. We conducted a study to determine the physiological status of adults trapped by a sex pheromone and floral odor. In the immigrant group, the number of males trapped by the floral odor was greater than the number caught by sex pheromone trapping. The volume of testes was similar in the above two trapping methods but was smaller than in the sweep net method. The ovary developmental grade, mating rate, and number of matings of females caught in floral odor trap were higher than in those caught in the sweep net. In the local breeding group, the number of males trapped by sex pheromones was greater than the number trapped by the floral odor. The volume of testes was smaller in the floral odor trap compared to the pheromone trap group, with the largest in the sweep net group. The ovarian developmental grade, mating rate, and number of matings of females were significantly higher in the floral odor trap group than in the sweep net group. In the emigrant group, the adult olfactory response to the sex pheromone and floral odor was low. The volume of testes was larger in the sweep net group compared to the moths caught by floral odor trapping. The number of eggs laid by female immigrants trapped by the floral odor and sweep net was similar, while the number in the local breeding group was greater in moths caught with the sweep net in comparison with those caught by the floral odor trap. The difference in egg hatchability between the two trapping methods in both immigrants and local breedings was not significant. Full article
(This article belongs to the Special Issue Recent Advances in Migrant Insect Pests)
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10 pages, 2078 KiB  
Article
The Asymmetric Total Synthesis of the Female-Produced Sex Pheromone of the Tea Tussock Moth
by Zhi-Feng Sun, Hao Liu, Yi-Fan Li, Yan-Ping Duan, Ling-Xia Jin, Xiao-Hui Ji, Hui-Ping Dai and Jiu-Fu Lu
Molecules 2024, 29(16), 3866; https://doi.org/10.3390/molecules29163866 - 15 Aug 2024
Cited by 4 | Viewed by 1128
Abstract
The tea tussock moth is a pest that damages tea leaves, affecting the quality and yield of tea and causing huge economic losses. The efficient asymmetric total synthesis of the sex pheromone of the tea tussock moth was achieved using commercially available starting [...] Read more.
The tea tussock moth is a pest that damages tea leaves, affecting the quality and yield of tea and causing huge economic losses. The efficient asymmetric total synthesis of the sex pheromone of the tea tussock moth was achieved using commercially available starting materials with a 25% overall yield in 11 steps. Moreover, the chiral moiety was introduced by Evans’ template and the key C-C bond construction was accomplished through Julia–Kocienski olefination coupling. The synthetic sex pheromone of the tea tussock moth will facilitate the subsequent assessment and implementation of pheromones as environmentally friendly tools for pest management. Full article
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14 pages, 1511 KiB  
Article
Enantioselective Synthesis of the Active Sex Pheromone Components of the Female Lichen Moth, Lyclene dharma dharma, and Their Enantiomers
by Yun Zhou, Jianan Wang, Yueru Zhang, Xiaochen Fu, Hongqing Xie, Jinlong Han, Jianhua Zhang, Jiangchun Zhong and Chenggang Shan
Molecules 2024, 29(12), 2918; https://doi.org/10.3390/molecules29122918 - 19 Jun 2024
Viewed by 1326
Abstract
The Lichen moth, Lyclene dharma dharma (Arctiidae, Lithosiinae), plays a significant role in forest ecosystem dynamics. A concise and novel method to synthesize the active sex pheromone components, (S)-14-methyloctadecan-2-one ((S)-1), (S)-6-methyloctadecan-2-one (( [...] Read more.
The Lichen moth, Lyclene dharma dharma (Arctiidae, Lithosiinae), plays a significant role in forest ecosystem dynamics. A concise and novel method to synthesize the active sex pheromone components, (S)-14-methyloctadecan-2-one ((S)-1), (S)-6-methyloctadecan-2-one ((S)-2), and their enantiomers has been developed. Key steps in the synthesis include the use of Evans’ chiral auxiliaries, Grignard cross-coupling reactions, hydroboration–oxidation, and Wacker oxidation. The synthesized sex pheromone components hold potential value for studies on communication mechanisms, species identification, and ecological management. Full article
(This article belongs to the Special Issue Synthesis of Bioactive Compounds: Volume II)
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10 pages, 1044 KiB  
Article
Asymmetric Synthesis of Three Alkenyl Epoxides: Crafting the Sex Pheromones of the Elm Spanworm and the Painted Apple Moth
by Yun Zhou, Jianan Wang, Beijing Tian, Yanwei Zhu, Yujuan Zhang, Jinlong Han, Jiangchun Zhong and Chenggang Shan
Molecules 2024, 29(9), 2136; https://doi.org/10.3390/molecules29092136 - 4 May 2024
Viewed by 1642
Abstract
A concise synthesis of the sex pheromones of elm spanworm as well as painted apple moth has been achieved. The key steps were the alkylation of acetylide ion, Sharpless asymmetric epoxidation and Brown’s P2-Ni reduction. This approach provided the sex pheromone of the [...] Read more.
A concise synthesis of the sex pheromones of elm spanworm as well as painted apple moth has been achieved. The key steps were the alkylation of acetylide ion, Sharpless asymmetric epoxidation and Brown’s P2-Ni reduction. This approach provided the sex pheromone of the elm spanworm (1) in 31% total yield and those of the painted apple moth (2, 3) in 26% and 32% total yields. The ee values of three final products were up to 99%. The synthesized pheromones hold promising potential for use in the management and control of these pests. Full article
(This article belongs to the Section Organic Chemistry)
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