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Journal articles on the topic 'Pheromone synthesis'

Author: Grafiati

Published: 5 June 2025

Last updated: 24 June 2025

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1

Mori, Kenji. "Recent results in the synthesis of ecologically important bioregulators." Pure and Applied Chemistry 73, no. 3 (2001): 601–6. http://dx.doi.org/10.1351/pac200173030601.

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Absolute configuration was established for the following semiochemicals: (S)-polyzonimine (1), (S)-9-methylgermacrene-B (2) and (1S,3S,7R)-3-methyl-a-himachalene (3). The stereoisomers of 2,6-dimethylheptane-1,7-diol monotetrahydropyranyl ether served as useful building blocks for the synthesis of syn- or anti-1,5-dimethylated aliphatic pheromones such as 4 and 5. Synthesis of analogs of the Israeli pine bast scale pheromone 6, which exhibits both pheromonal and kairomonal activities, enabled us to find a strong pheromone mimic 7 without any kairomonal activity.

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2

Balykina, E. B., V. E. Glebov, D. A. Korzh, et al. "Development of a pheromone preparation for the detection and monitoring of boxwood moth Cydalima perspectalis Walker." Bulletin of the State Nikitsky Botanical Gardens, no. 134 (April 9, 2020): 138–43. http://dx.doi.org/10.36305/0513-1634-2020-134-138-143.

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The results of field tests of different variants of synthetic pheromone blends and pheromone dispenser developed by the Department of synthesis and application of pheromones of the FSFI " All-Russia Plant Quarantine Center" for identification and monitoring boxwood moth is a dangerous invasive pest of boxwood in the Republic of the Crimea; the optimal material of the pheromone’s carrier is determined, the effective ratio and dosage are proposed.

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3

Song, Xue, Yabei Xu, Sainan Zhang, et al. "Identification and Expression Analysis of the FAD Gene Family in Anoplophora glabripennis (Coleoptera: Cerambycidae) Based on Genome-Wide Data." Forests 15, no. 4 (2024): 690. http://dx.doi.org/10.3390/f15040690.

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Pheromones play an important role in mate choice in insects, and pheromone synthesis pathways are potential targets for the control of harmful insects, among which desaturation is of great significance in pheromone structural diversity. However, little is known about the desaturase genes regulating pheromone synthesis in Coleoptera. In this study, taking the internationally significant pest Anoplophora glabripennis as a research object, we identified 6 AglaFAD genes, all of which were mapped to the endoplasmic reticulum and shared a highly similar distribution of conserved domains. A phylogenetic analysis showed that AglaFAD1–2 and AglaFAD3–6 exerted desaturation at different positions of the acyl chain, respectively. In regard to the expression levels of these six AglaFADs in both sexes, six tissues and three developmental stages were analyzed by qPCR. Combined with the chemical composition of the female pheromones that have been identified, two candidate genes, AglaFAD2 and AglaFAD5, which are specifically expressed in females, were screened, showing higher expression levels before mating and significantly decreasing after mating. It is speculated that they may be involved in the biosynthesis of contact pheromones in females. These results provide a basis for detailed functional studies of candidate genes in insect pheromone synthesis.

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M H, Suchithra Kumari, Dharna Bisen, Jayant J P, Himanshu Sekhar Behera, Barinderjit Singh, and Amit Lohar. "Insect Behaviour Modulation Using Pheromones: Trends and Applications." UTTAR PRADESH JOURNAL OF ZOOLOGY 46, no. 11 (2025): 175–85. https://doi.org/10.56557/upjoz/2025/v46i115017.

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Pheromones are chemical signals secreted by insects that influence the behavior of conspecifics, playing a pivotal role in communication related to mating, aggregation, foraging, and defense. This review explores the advances in understanding insect behavioral modulation through pheromones, with a focus on contemporary trends and real-world applications. Emphasis is placed on the ecological functions of various pheromone types, mechanisms of detection, and behavioral outcomes. Emerging technologies in pheromone synthesis, controlled release systems, and gene-editing for pheromone production are also discussed. Practical applications such as mating disruption, mass trapping, lure-and-kill strategies, and integrated pest management (IPM) highlight the potential of pheromones in sustainable agriculture. The paper further outlines challenges including pheromone degradation, species-specificity, and resistance. By integrating ecological insights with biotechnological innovations, pheromone-based approaches offer a promising, eco-friendly alternative to conventional insecticides, reducing environmental impact while enhancing crop protection.

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5

Khandayataray, P., M. K. Murthy, D. Samal, and G. Gurusubramanian. "Sustainable Integrated Pest Management using Pheromones: Types, Synthesis, Mechanism of Action and Applications." Research Journal of Biotechnology 19, no. 2 (2023): 140–57. http://dx.doi.org/10.25303/1902rjbt1400157.

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Integrated pest management (IPM) strategies have been developed to combat the health, environmental and organismal adverse effects of conventional pesticides. It is possible to control agricultural and forestry pests by using insect pheromones. Recently, pheromone research has been influenced significantly by advances in agriculture as well as in technical aspects. Pheromone research is discussed in this review including synthesis, mechanism and application in integrated pest management. Moreover, the synthesis of certain chiral, racemic, monoolefinic and poly-olefinic pheromones has evolved a standard method for the manufacture of similar compounds. IPM is concluded with an in-depth discussion of pheromones' role in IPM. Further, it provides faster directions to organic chemists and entomologists in the development of eco-friendly tools. Future green agriculture will depend heavily on pheromones for its sustainability.

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6

Zeng, Fangfang, Haixin Jiang, Haoqi Xu, Ruotong Shen, and Dianxuan Wang. "Comparative Transcriptomics Analysis Reveals Rusty Grain Beetle’s Aggregation Pheromone Biosynthesis Mechanism in Response to Starvation." Insects 15, no. 2 (2024): 137. http://dx.doi.org/10.3390/insects15020137.

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Pheromones are the basis of insect aggregation, mating, and other behaviors. Cucujoid grain beetles produce macrocyclic lactones as aggregation pheromones, yet research on their biosynthesis at the molecular level remains limited. The rusty grain beetle, C. ferrugineus, is an important economic species in China. Although two aggregation pheromone components have been identified, their suspected biosynthesis via the MVA pathway and the FAS pathway lacks molecular elucidation. Previous evidence supports that starvation affects the production of aggregation pheromones. Therefore, we constructed comparative transcriptome libraries of pheromone production sites in C. ferrugineus under starvation stress and identified genes related to pheromone biosynthesis and hormone regulation. A total of 2665 genes were significantly differentially expressed, of which 2029 genes were down-regulated in starved beetles. Putative C. ferrugineus genes directly involved in pheromone biosynthesis were identified, as well as some genes related to the juvenile hormone (JH) pathway and the insulin pathway, both of which were depressed in the starved beetles, suggesting possible functions in pheromone biosynthesis and regulation. The identification of genes involved in macrolide lactone biosynthesis in vivo holds great significance, aiding in the elucidation of the synthesis and regulatory mechanisms of cucujoid grain beetle pheromones.

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7

Rajchard, J. "Sex pheromones in amphibians: a review ." Veterinární Medicína 50, No. 9 (2012): 385–89. http://dx.doi.org/10.17221/5637-vetmed.

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Amphibians are interesting animals, very often kept by aquarists and vivarists. Their ability of intraspecific chemical signalization belongs to very interesting biological features. The skin glands of anurans secrete various biologically active compounds. The pheromones are peptides consisting of various numbers of amino acid residues and their synthesis is regulated by hormones (e.g. prolactin and androgens). Similarly, the responsiveness of the vomeronasal epithelium to some of these compounds is enhanced by some hormonal substances (prolactin and oestrogen). Hypophyseal hormones, arginine vasotocin and gonadotropin-releasing hormone are involved in the humoral regulation of pheromone discharge. The storage of some compounds with pheromonal activity in a biologically inactive form was also proved. The pheromones have an important role in sexual relationships. These chemosignals increase female receptivity and are probably involved in the mate choice. The courtship pheromone signals may be conserved across related species. Chemosignals play an important role in female attraction and/or territorial announcement. In addition to sex pheromones, various neuropeptides, antimicrobial and other biologically active peptides were found in skin glands of these amphibians. The infochemical system can be disturbed by a chemical influence in the environment.

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8

Morales, Juan Enrique Tacoronte, María Teresa Cabrera Pedroso, Kenia Silvana Holguín García, and Andrea Cevallos Camacho. "A Simple and Sustainable Synthetic Lab-Protocol for Obtaining Racemic Dominicalure-Aggregation Pheromone of the Grain Beetle Rhyzopertha dominica F. (Coleoptera, Bostrichidae)." Chemistry Proceedings 3, no. 1 (2020): 130. http://dx.doi.org/10.3390/ecsoc-24-08284.

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The pheromones constitute a decisive component in the strategies for the conservation of stored foods. In Ecuador, several studies are developing, under eco sustainable conditions, on synthetic pheromones and their applicability in the control of species Rhyzopertha dominica, which causes severe damage in stored grains. Previously reported information details the use of expensive reagents for carrying out the synthesis of the aggregation pheromone of this species. Using propionic and isobutiric aldehydes as starting substrates by means of aldolic condensation, selective oxidation with Ag2O-methanol of monoenic aldehydes, treatment with SOCl2, and esterification with 2-pentanol, the respective components of the racemic aggregation pheromone of this species were synthesized.

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9

Sharma, Madan L., and Sadhana Verma. "Stereoselective synthesis of (Z)-7-octadecenyl isovalerate, a sex pheromone of Euproctis similis xanthocampa." Collection of Czechoslovak Chemical Communications 56, no. 9 (1991): 1916–18. http://dx.doi.org/10.1135/cccc19911916.

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I simple stereoselective synthesis of (Z)-7-octadecen-1-yl isovalerate (I), a sex pheromone of Euproctis similis xanthocampa has been achieved trough an unambiguous route. The isovalerate type of sex pheromones was discovered in Limantxiidase for the first time.

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10

Umezawa, Taiki, Misaki Hara, Nana Kinoshita-Terauchi, and Fuyuhiko Matsuda. "Enantioselective Total Synthesis of Multifidene, a Sex Pheromone of Brown Algae." Organics 3, no. 3 (2022): 187–95. http://dx.doi.org/10.3390/org3030015.

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The total synthesis of multifidene, a sex pheromone found in brown algae, is described. The synthesis features the highly enantioselective and diastereoselective addition reaction of an aldehyde to a nitroolefin in the presence of a Hayashi–Jørgensen catalyst and a Nef reaction initiated by visible light irradiation. These key reactions enabled the 11-step synthesis from commercially available compounds. The synthetic pheromones are examined with gametes.

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11

Warsito, Warsito, Edi Priyo Utomo, Achmad Ashadi, and Satriyo Santosa. "THE USE OF GRIGNARD REAGENT IN PHEROMONE SYNTHESIS FOR PALM WEEVIL (Rhynchorus, Sp)." Indonesian Journal of Chemistry 3, no. 3 (2010): 141–44. http://dx.doi.org/10.22146/ijc.21878.

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In an integrated controlling system of palm weevil, using of synthetic feromoid is strickly needed. The research is aimed to synthesize pheromone which secreted by the weevil, e.g. 4-methyl-5-nonanol (R. ferrugineus) and 3-methyl-4-octanol (R. schach) through Grignard reagent which formed in situ. The synthesis was proceded by retrosynthesis to determine the precursor, valeraldehyde. The precursor was reacted with Grignard reagent of sec-amyl magnesium bromide (R. ferrugenieus) and sec-butyl magnesium bromide (R. shach) which made in situ. Characterization of the synthetic molecular pheromone was performed by Gas Chromatography-mass spectroscopy and Fourier Transformed Infra Red. The bioassay of the molecule was carried out by olfactometer. The result showed that the conversion of the reactions were 51.28% (4-methyl-5-nonanol) and 85.90% (3-methyl-4-octanol). The character of physico-chemical and bioactivity of the synthetic pheromone are identic with natural pheromones. Keywords: palm weevil, pheromone, grignard reagent

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12

Noorbakhsh, Saeede, Babak Heidary Alizadeh, Moosa Saber, and Hossein Farazmand. "Improved Synthesis of (Z,E)-9,11,13-Tetradecatrienal, the Sex Pheromone of the Carob Moth Apomyelois (=Ectomyelois) Ceratoniae (Lepidoptera: Pyralidae)." Journal of Chemical Research 41, no. 4 (2017): 199–201. http://dx.doi.org/10.3184/174751917x14894997017450.

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(Z,E)-9,11,13-Tetradecatrienal is a sex pheromone component emitted by virgin females of the Carob Moth Apomyelois ceratoniae Zeller (Lepidoptera: Pyralidae) which is an important pest of Iranian pomegranate fruits. Chemical control of this pest is not possible and biological methods with pheromones are used. The synthesis of the major component of the sex pheromone was achieved in fewer steps and with lower cost than previously. (Z,E)-9,11,13-Tetradecatrienal was synthesised by four steps with 59% overall yield. The coupling of a conjugated dienynol intermediate from E-1,2-dichloroethylene with vinyl magnesium bromide was achieved in good yield and followed by reduction of dienynol with activated zinc in THF-H2O and oxidation gave the aldehyde of the sex pheromone.

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13

La Terza, Antonietta, Nicoleta Dobri, Claudio Alimenti, Adriana Vallesi, and Pierangelo Luporini. "The water-borne protein signals (pheromones) of the Antarctic ciliated protozoan Euplotes nobilii: structure of the gene coding for the En-6 pheromoneThis article is one of a selection of papers in the Special Issue on Polar and Alpine Microbiology." Canadian Journal of Microbiology 55, no. 1 (2009): 57–62. http://dx.doi.org/10.1139/w08-122.

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The marine Antarctic ciliate, Euplotes nobilii , secretes a family of water-borne signal proteins, denoted as pheromones, which control vegetative proliferation and mating in the cell. Based on the knowledge of the amino acid sequences of a set of these pheromones isolated from the culture supernatant of wild-type strains, we designed probes to identify their encoding genes in the cell somatic nucleus (macronucleus). The full-length gene of the pheromone En-6 was determined and found to contain an open-reading frame specific for the synthesis of the En-6 cytoplasmic precursor (pre-pro-En-6), which requires 2 proteolytic cleavages to remove the signal peptide (pre) and the prosegment before secretion of the mature protein. In contrast to the sequence variability that distinguishes the secreted pheromones, the pre- and pro-sequences appear to be tightly conserved and useful for the construction of probes to clone every other E. nobilii pheromone gene. Potential intron sequences in the coding region of the En-6 gene imply the synthesis of more En-6 isoforms.

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14

Sun, Zhi-Feng, Hao Liu, Yi-Fan Li, et al. "The Asymmetric Total Synthesis of the Female-Produced Sex Pheromone of the Tea Tussock Moth." Molecules 29, no. 16 (2024): 3866. http://dx.doi.org/10.3390/molecules29163866.

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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.

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15

Takuya, Tashiro, and Mori Kenji. "Pheromone synthesis. Part-209 : Synthesis of candidate structures for homosesquiterpene alcohols found as a putative sex pheromone from the sandfly Lutzomyia lichyi." Journal of Indian Chemical Society Vol. 77, Nov-Dec 2000 (2000): 617–19. https://doi.org/10.5281/zenodo.5869624.

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Department of Chemistry, Faculty of Science, Science University of Tokyo, Kagurazaka 1-3, Shinjuku-ku, Tokyo 162-8601, Japan <em>Fax : </em>81-3-3235-2214 <em>Manuscript received 13 October 2000</em> Racemic and diastereomeric mixture of three homosesquiterpene alcohols 2, 3 and 4 were synthesized from a raceme and diastereomeric mixture of 3-methyl-a-himachalene (1) or from its synthetic precursor, 2-nor-ketone (5). These alcohols 2, 3 and 4 exhibited mass spectra not identical with those reported for the homosesquiterpene alcohols found as a putative sex pheromone in the hexane extract of the male sandfly <em>Lutzomyia lichyi.</em>

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16

Melnik, Kristina, Christopher Grimm, Johannes Wittbrodt, Joachim Ruther, and Stefan Schulz. "Enantioselective synthesis and determination of the absolute configuration of the male sex pheromone of the parasitoid wasp Urolepis rufipes." Organic & Biomolecular Chemistry 18, no. 18 (2020): 3463–65. http://dx.doi.org/10.1039/d0ob00614a.

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The parasitoid wasp Urolepis rufipes uses terminally oxidized dihydrolinalool as a sex pheromone. The absolute configuration of the active enantiomer was established as 2S,6S by synthesis and its pheromonal activity was proven in a bioassay.

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17

Le, Thanh C., and Kamlesh R. Chauhan. "Simple and Short Synthesis of Trans-(R)-Nerolidol, a Pheromone Component of Fruit Spotting Bug." Natural Product Communications 9, no. 3 (2014): 1934578X1400900. http://dx.doi.org/10.1177/1934578x1400900302.

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A three-step synthesis of enantiomerically pure ( R) and ( S)- trans nerolidol from commercially available E, E-fanesol is described. Trans nerolidol is an abundant sesquiterpene in many plant species, almost enantiomerically pure; however, the configuration of chirality is S. There is no natural resource for R-trans nerolidol, which has recently been identified as a pheromone component of the fruit spotting bug Amblypelta lutescens. The simple syntheses reported here will make enantiomerically pure R- and S-trans nerolidol and homologues available for further research and ultimately for use in integrated pest management strategies comprising pheromones.

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18

Wyatt, Tristram D. "The search for human pheromones: the lost decades and the necessity of returning to first principles." Proceedings of the Royal Society B: Biological Sciences 282, no. 1804 (2015): 20142994. http://dx.doi.org/10.1098/rspb.2014.2994.

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As humans are mammals, it is possible, perhaps even probable, that we have pheromones. However, there is no robust bioassay-led evidence for the widely published claims that four steroid molecules are human pheromones: androstenone, androstenol, androstadienone and estratetraenol. In the absence of sound reasons to test the molecules, positive results in studies need to be treated with scepticism as these are highly likely to be false positives. Common problems include small sample sizes, an overestimate of effect size (as no effect can be expected), positive publication bias and lack of replication. Instead, if we are to find human pheromones, we need to treat ourselves as if we were a newly discovered mammal, and use the rigorous methods already proven successful in pheromone research on other species. Establishing a pheromone relies on demonstration of an odour-mediated behavioural or physiological response, identification and synthesis of the bioactive molecule(s), followed by bioassay confirmation of activity. Likely sources include our sebaceous glands. Comparison of secretions from adult and pre-pubertal humans may highlight potential molecules involved in sexual behaviour. One of the most promising human pheromone leads is a nipple secretion from the areola glands produced by all lactating mothers, which stimulates suckling by any baby not just their own.

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19

Wang, Qing-Hai, Xing Gao, Hong-Song Yu, Ze Zhang, and Quan-You Yu. "Exploring the Terminal Pathway of Sex Pheromone Biosynthesis and Metabolism in the Silkworm." Insects 12, no. 12 (2021): 1062. http://dx.doi.org/10.3390/insects12121062.

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Sex pheromones are vital to sexual communication and reproduction in insects. Although some key enzymes in pheromone production have been well studied, information on genes involved in the terminal pathway is limited. The domestic silkworm employs a pheromone blend containing (E,Z)-10,12-hexadecadienol (bombykol) and analogous (E,Z)-10,12-hexadecadienal (bombykal); whereas, its wild ancestor B. mandarina uses only bombykol. The two closely related moths might be a good model for exploring the genes involved in aldehyde pheromone synthesis and metabolism. By deep sequencing and analyzing the sex pheromone gland (PG) transcriptomes; we identified 116 candidate genes that may be related to pheromone biosynthesis, metabolism, and chemoreception. Spatiotemporal expression profiles and differentially expressed analysis revealed that four alcohol oxidases (BmorAO1; 2; 3; and 4); one aldehyde reductase (BmorAR1); and one aldehyde oxidase (BmorAOX5) might be involved in the terminal pathway. Phylogenetic analysis showed that, except for BmorAO3 and MsexAO3, AOs did not show a conversed orthologous relationship among moths; whereas, ARs and AOXs were phylogenetically conserved. This study provides crucial candidates for further functional elucidation, and which may be utilized as potential targets to disrupt sexual communication in other moth pests.

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20

Rajkhowa, Abhigyan, Monimala Saikia, Dipankar Brahma, et al. "Chemical Communication between Male and Female Sex of Bombyx mori." Archives of Current Research International 24, no. 6 (2024): 37–47. http://dx.doi.org/10.9734/acri/2024/v24i6762.

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Communication involves the systematic and symbolic exchange of information between entities. In insects, the most significant form of communication occurs between members of the same species. Silkworms primarily utilize pheromones for communication. Bombykol, the sex pheromone released by the female silk moth Bombyx mori, was first extracted by Adolf Butenandt. The biosynthesis of bombykol occurs in the pheromone gland, where various enzymes and genes participate in the biosynthesis process through an influx of extracellular Ca2+. Bombykol-sensitive ORNs are located on the antennae of male moths, which perceive the bombykol released by female moths. These ORNs are so sensitive that even a single pheromone molecule can generate an electric signal in the male moth. Once the male moth detects the bombykol molecule, the Pheromone Binding Protein plays a crucial role in enabling it to bind to the receptor without disruption. Mori, B. The substance is rapidly eliminated from its receptor site and rendered inactive by phenomenol-degrading enzymes and alcohol oxidase genes. Numerous studies and tests conducted on B. mori's sex pheromone have yielded important insights into the molecular and genetic aspects for the chemical interactions with male and female silkworms, which including the synthesis, behavioral reaction, and the perception of bombykol.

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21

Lu, Zhengchang, Wei Liu, Hongyu Pan, and Dawei Zhang. "Design, Synthesis, and Biological Evaluation of the Sex Pheromone of the Asian Corn Borer, Ostrinia furnacalis (Guenée)." Journal of Chemistry 2018 (2018): 1–7. http://dx.doi.org/10.1155/2018/1520939.

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A convenient total synthesis of (Z)-12-tetradecenyl acetate (1a) and (E)-12-tetradecenyl acetate (1b), which are the sex pheromones of Ostrinia furnacalis (Guenée), has been achieved. The target mixture molecules, of a cis-to-trans-isomer ratio of 27 to 73, were synthesized in 40% overall yield and through [13C + 1C] synthetic strategy in five steps from commercially available and cheap industrial brassylic acid as key starting material. The electroantennogram (EAG) responses of synthetic sex pheromone to ACB male moths were conducted. The results showed that the target mixture molecules were found to have a good activity and displayed significantly stronger EAG responses ranging from 10 to 1000 μg, and the optimized stimulating dosage of the activity of synthetic sex pheromone to ACB males is 10 μg. Compared with the existing routes, this synthetic approach is operationally simple, good-yielding, and cost-effective, which could serve as a basis for developing the techniques of sex pheromone mass trapping or mating disruption and providing an environmentally benign method to control ACB pests.

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22

Miller, David, François Bilodeau, and Robert H. Burnell. "Stereoselective syntheses of isomers of 3,7-dimethylnonadecane, a sex pheromone of the alfalfa blotch leafminer (Agromyza frontella (Rondani))." Canadian Journal of Chemistry 69, no. 7 (1991): 1100–1106. http://dx.doi.org/10.1139/v91-163.

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Two related stereoselective syntheses of 3,7-dimethylnonadecane, a sex pheromone of the alfalfa leafminer, are described to show that pulegone can serve as a useful starting material for the preparation of chiral aliphatic isoprenoid compounds. The schemes are designed to place the stereogenic center of pulegone at C.3 in one synthesis and at C.7 in the other so that the optical properties of the products can be compared with one another and with the values calculated using Brewster's rules. Key words: chiral hydrocarbons, stereoselective synthesis, pheromone, Agromyza frontella.

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23

Zhou, Yun, Jianan Wang, Beijing Tian, et al. "Asymmetric Synthesis of Three Alkenyl Epoxides: Crafting the Sex Pheromones of the Elm Spanworm and the Painted Apple Moth." Molecules 29, no. 9 (2024): 2136. http://dx.doi.org/10.3390/molecules29092136.

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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.

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24

Yakovleva, Marina Petrovna, Valentina Afanasievna Vydrina, Nailya Mavletzyanovna Ishmuratova, and Gumer Yusupovich Ishmuratov. "OPTICALLY ACTIVE PINE SEX PHEROMONE SAWS: SYNTHESIS AND BIOLOGICAL ACTIVITY." chemistry of plant raw material, no. 2 (June 12, 2024): 26–54. https://doi.org/10.14258/jcprm.20240312696.

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The most dangerous pest for coniferous trees, by right, can be called pine sawflies of the genera Diprion, Neodiprion and Gilpinia (Diprionidae) – insects that can cause tremendous harm to plants or even destroy them. Scots pines suffer the most from the pest, especially at the age of 20–40, however, ornamental plant species are often subject to mass attack by insects. The review article presents mechanical, biological and chemical methods of combating pine sawflies, the main part of the review is devoted to the use of the sex pheromone of males of these pests, namely, identification methods (isolation, physicochemical methods of analysis, electrophysiological experiments and field tests) of pine sawfly pheromone, stereoisomeric 3,7-dimethylpentadecan-1-ol (diprionol) acetate and propionate, and presents a list of publications on known syntheses of their racemic compounds forms, methods for controlling insect pests are described and all known chemical syntheses of possible stereomers of diprionol and its esters are presented individually or in a mixture with various degrees of optical purity. The review includes the following chapters: Introduction; The structure of the pine sawfly pheromone and its biological activity; Synthesis of stereoisomers of pine sawfly pheromone; Conclusion. The review includes 93 literature references.

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25

Tupec, Michal, Aleš Buček, Irena Valterová, and Iva Pichová. "Biotechnological potential of insect fatty acid-modifying enzymes." Zeitschrift für Naturforschung C 72, no. 9-10 (2017): 387–403. http://dx.doi.org/10.1515/znc-2017-0031.

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AbstractThere are more than one million described insect species. This species richness is reflected in the diversity of insect metabolic processes. In particular, biosynthesis of secondary metabolites, such as defensive compounds and chemical signals, encompasses an extraordinarily wide range of chemicals that are generally unparalleled among natural products from other organisms. Insect genomes, transcriptomes and proteomes thus offer a valuable resource for discovery of novel enzymes with potential for biotechnological applications. Here, we focus on fatty acid (FA) metabolism-related enzymes, notably the fatty acyl desaturases and fatty acyl reductases involved in the biosynthesis of FA-derived pheromones. Research on insect pheromone-biosynthetic enzymes, which exhibit diverse enzymatic properties, has the potential to broaden the understanding of enzyme specificity determinants and contribute to engineering of enzymes with desired properties for biotechnological production of FA derivatives. Additionally, the application of such pheromone-biosynthetic enzymes represents an environmentally friendly and economic alternative to the chemical synthesis of pheromones that are used in insect pest management strategies.

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Qu, Cheng, Zhiwei Kang, Biyun Zhang, et al. "Genome-Wide Identification and Expression Profiling of Candidate Sex Pheromone Biosynthesis Genes in the Fall Armyworm (Spodoptera frugiperda)." Insects 13, no. 12 (2022): 1078. http://dx.doi.org/10.3390/insects13121078.

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Spodoptera frugiperda is an agricultural pest causing substantial damage and losses to commercial crops. Sex pheromones are critical for successful mating in Lepidoptera and have been used for monitoring and control of many pest species. The sex pheromone of S. frugiperda is known, but the genes involved in its biosynthesis have not been identified. We systematically studied 99 candidate sex pheromone genes in the genome of S. frugiperda including 1 acetyl-CoA carboxylase (ACC), 11 fatty acid synthases (FASs), 17 desaturases (DESs), 4 fatty acid transport proteins (FATPs), 29 fatty acyl-CoA reductases (FARs), 17 acetyl-CoA acetyltransferases (ACTs), 5 acyl-CoA dehydrogenase (ACDs), 3 enoyl-CoA hydratases (ECHs), 3 hydroxyacyl-CoA dehydrogenases (HCDs), 6 ethyl-CoA thiolases (KCTs), and 3 acyl-CoA-binding proteins (ACBPs). Based on the comparative transcriptome results, we found 22 candidate sex pheromone biosynthesis genes predominately expressed in pheromone glands (PGs) than abdomens without PGs including SfruFAS4, SfruFATP3, SfruACD5, SfruKCT3, SfruDES2, SfruDES5, SfruDES11, SfruDES13, SfruFAR1, SfruFAR2, SfruFAR3, SfruFAR6, SfruFAR7, SfruFAR8, SfruFAR9, SfruFAR10, SfruFAR11, SfruFAR14, SfruFAR16, SfruFAR29, SfruACT6, and SfruACT10. A combination of phylogenetic and tissue-specific transcriptomic analyses indicated that SfruDES5, SfruDES11, SfruFAR2, SfruFAR3, and SfruFAR9 may be key genes involved in the sex pheromone synthesis of S. frugiperda. Our results could provide a theoretical basis for understanding the molecular mechanisms of sex pheromone biosynthesis in S. frugiperda, and also provide new targets for developing novel pest control methods based on disrupting sexual communication.

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Wang, Xueyang, Jianan Wang, Fengbo Ma, Qinghua Bian, Min Wang, and Jiangchun Zhong. "Asymmetric Synthesis of Contact Sex Pheromone of Tetropium fuscum and Its Enantiomer." Molecules 27, no. 20 (2022): 6897. http://dx.doi.org/10.3390/molecules27206897.

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Tetropium fuscum is a harmful forest pest and attacks spruces. The contact sex pheromone of this pest, (S)-11-methyl-heptacosane, and its enantiomer were synthesized via Evans’ chiral auxiliaries. The key steps of this approach included acylation of carboxylic acid, diastereoselective methylation of oxazolidinone amide, and Wittig coupling of the aldehyde with chiral phosphonium salt. The synthetic pheromones would have potential utility in the control of this pest.

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28

Silva, Weliton D., Lawrence M. Hanks, Jean Carlos S. Alvarez, et al. "Variations on a Theme: Two Structural Motifs Create Species-Specific Pheromone Channels for Multiple Species of South American Cerambycid Beetles." Insects 11, no. 4 (2020): 222. http://dx.doi.org/10.3390/insects11040222.

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We describe the identification, synthesis, and field-testing of aggregation-sex pheromones, or likely pheromone candidates, of seven species of South American cerambycid beetles in the subfamily Cerambycinae, of the tribes Eburiini and Neoibidionini. Analyses of extracts of volatiles released by adult males revealed that Eburodacrys dubitata White produce 11-methyltridecanal, whereas the males of Eburodacrys assimilis Gounelle, Eburodacrys flexuosa Gounelle, and Eburodacrys lenkoi Napp and Martins produce blends of this compound, along with its analog 10-methyldodecanal. In contrast, males of Compsibidion graphicum (Thomson) and Compsibidion sommeri (Thomson) produce blends of 10-methyldodecanal and its corresponding alcohol 10-methyldodecanol. The results from field bioassays with synthetic compounds showed that each species was specifically attracted to traps containing their reconstructed pheromone blend. However, E. assimilis was not trapped, possibly due to inhibition by non-natural enantiomers in the racemic test compounds. During the trials for the Compsibidion species, adults of another cerambycid species, Tetraopidion mucoriferum (Thomson), were captured in significant numbers in traps baited with 10-methyldodecanol, suggesting that this compound is a pheromone component for this species. This study demonstrates another case of conservation of pheromone structures within South American cerambycid species. It also highlights how blends of closely related structures, differing only in chain length or functional group, make the evolution of species-specific pheromone channels possible.

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Ponmanickam, Ponnirul, Gnanasekaran Jebamercy, Govindaraju Archunan та Soundrapandian Kannan. "Detection of α2u-globulin in rat pup preputial gland by MALDI-TOF mass spectrometry". Current Zoology 55, № 4 (2009): 296–300. http://dx.doi.org/10.1093/czoolo/55.4.296.

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Abstract The α2u-globulin, a soluble protein identified in the urine and preputial gland of adult male rat is reported to be pheromone carrier. The pup preputial gland plays a significant role in chemical communication for mother-young interaction; however, the presence of a pheromone-carrying protein in the pup preputial gland has not been confirmed. Therefore, the present study was carried out to identify the α2u-globulin in the pup preputial gland by Matrix Assisted Laser Desorption Ionization Time of Flight mass spectrometry (MALDI-TOF). The preputial glands of prepubertal rats were subjected to one-dimensional SDS-PAGE. In-gel trypsin digestion of a 18 kDa band was carried out and analyzed by MALDI-TOF. The results of a MASCOT search showed the presence of α2u-globulin in the 18 kDa band. In contrast to the report of the synthesis of this protein only in adult rats, the identification of this protein in pup preputial gland is significant. The results suggest that synthesis of α2u-globulin in the rat preputial gland starts in the prepubertal stage itself. In prepubertal rats, the preputial gland is a source of pheromone for performing anogenital licking behaviour by the mother rat. Since α2u-globulin belongs to the lipocalin (ligand carrier) family, it might carry the volatile for processing pheromonal communication in mother-pup bonding in rat.

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30

HIROSATO, TAKIKAWA, TAMAGAWA HIDEKI, and MORI KENJI. "Pheromone Synthesis. Part-189. Synthesis of the Enantiomers of 6-Methyl-3-nonanone, the Female-produced Sex Pheromone of Caddisfly, Hesperophylax occidentalis." Journal of Indian Chemical Society Vol. 74, Nov-Dec 1997 (1997): 855–57. https://doi.org/10.5281/zenodo.5900350.

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Department of Chemistry, Faculty of Science, Science University of Tokyo, Kagurazaka 1-3, Shmjuku-ku, Tokyo 162, Japan <em>Manuscript received 27 August 1997</em> Both the enantiomers of 6-methyl-3-nonanone (1), the female-produced sex pheromone of the caddisfly (<em>Hesperophylax occidentalis</em>) have been synthesized by starting from the enantiomers of citronellaI (2).

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31

An, Biyu, Shengli Liu, Jianan Wang, Dan Liu, Qinghua Bian, and Jiangchun Zhong. "A Concise Asymmetric Synthesis of Sex Pheromone of Euproctis pseudoconspersa (Strand) and Its Enantiomer." Molecules 30, no. 12 (2025): 2494. https://doi.org/10.3390/molecules30122494.

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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.

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32

Mori, Kenji. "Organic Synthesis in Pheromone Science." Molecules 10, no. 9 (2005): 1023–47. http://dx.doi.org/10.3390/10091023.

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33

Mori, K. "Recent results in pheromone synthesis." Pure and Applied Chemistry 68, no. 11 (1996): 2111–18. http://dx.doi.org/10.1351/pac199668112111.

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34

Mori, Kenji, and Masaharu Ishikura. "Pheromone Synthesis, CXVII Synthesis of Sitophilate, the Aggregation Pheromone ofSitophilus granarius L., and Its Antipode." Liebigs Annalen der Chemie 1989, no. 12 (1989): 1263–65. http://dx.doi.org/10.1002/jlac.1989198902101.

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35

NISHIMURA, Y., and K. MORI. "ChemInform Abstract: Pheromone Synthesis. Part 188. A New Synthesis of (-)-Frontalin, the Bark Beetle Pheromone." ChemInform 29, no. 24 (2010): no. http://dx.doi.org/10.1002/chin.199824203.

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36

Wu, Zhongtao, Manuel Jäger, Jeffrey Buter, and Adriaan J. Minnaard. "A protecting group-free synthesis of the Colorado potato beetle pheromone." Beilstein Journal of Organic Chemistry 9 (November 6, 2013): 2374–77. http://dx.doi.org/10.3762/bjoc.9.273.

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A novel synthesis of the aggregation pheromone of the Colorado potato beetle, Leptinotarsa decemlineata, has been developed based on a Sharpless asymmetric epoxidation in combination with a chemoselective alcohol oxidation using catalytic [(neocuproine)PdOAc]2OTf2. Employing this approach, the pheromone was synthesized in 3 steps, 80% yield and 86% ee from geraniol.

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37

Conway, Jeremy C., Peter Quayle, Andrew C. Regan, and Christopher J. Urch. "Palladium mediated spiroketal synthesis: application to pheromone synthesis." Tetrahedron 61, no. 50 (2005): 11910–23. http://dx.doi.org/10.1016/j.tet.2005.09.055.

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38

Mori, Kenji, and Kunio Fukamatsu. "Pheromone Synthesis, CXXXVII. A New Synthesis of (+)-Grandisol." Liebigs Annalen der Chemie 1992, no. 5 (1992): 489–93. http://dx.doi.org/10.1002/jlac.199219920187.

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39

Alderdice, Margot, Claude Spino, and Larry Weiler. "The synthesis of the isomeric components of San Jose scale pheromone — an illustration of a stereospecific synthesis of trisubstituted alkenes." Canadian Journal of Chemistry 71, no. 11 (1993): 1955–63. http://dx.doi.org/10.1139/v93-242.

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The three isomeric components of the San Jose scale pheromone, 5–7, have been synthesized from a common β-keto ester intermediate. A study of the alkylation of the dianion of methyl acetoacetate with a series of alkylating agents with the same carbon skeleton has been carried out. The trisubstituted alkenes in 5 and 6 have been synthesized stereospecifically via a copper-catalyzed coupling of a methyl Grignard reagent with the E or Z enol phosphate from the alkylated β-keto ester. In the case of the Z enol derivative, the coupling reaction was carried out on the diethyl- and diphenylphosphates, and the enol triflate. The diethyl enol phosphate gave the highest stereoselectivity. The synthetic pheromones were attractive to San Jose scale in the field.[Formula: see text]

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40

Ishmuratov, Gumer Yu, Marina P. Yakovleva, Valentina A. Vydrina, Evelina R. Nurieva, Nailya M. Ishmuratova, and Marat G. Giniatullin. "TELOMERS OF 1,3-BUTADIENE WITH WATER AND CARBON OXIDE IN DIRECTED SYNTHESIS OF INSECT’S PHEROMONES." IZVESTIYA VYSSHIKH UCHEBNYKH ZAVEDENII KHIMIYA KHIMICHESKAYA TEKHNOLOGIYA 62, no. 10 (2019): 49–60. http://dx.doi.org/10.6060/ivkkt.20196210.5955.

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Insect pheromones fit well into the modern concept of integrated plant protection, the main purpose of which is not the complete destruction of insect pests, but the management of their number without affecting or affecting to a minimum extent all other organisms in the biocenosis. Since pheromones are produced in insect organisms most often in nanogram quantities, the only way to obtain them for practical purposes is through multi-stage chemical synthesis. In connection with the achievements of metal complex catalysis, a number of oligomers, co-oligomers, and telomeres of lower 1,3-dienes of regular structure became available, therefore, the study of the chemo-, stereo-, and regioselective pathways for the conversion of these substrates into practically important low-molecular insect bioregulators is relevant. The author’s review presents the results of studies of the laboratory of insect bioregulators of the Ufa Institute of Chemistry of the Ufa Scientific Center of the Russian Academy of Sciences on the use of available synthetic telomeres of 1,3-butadiene with water and carbon monoxide – 2E,7-octadiene-1-ol and isopropyl-3E,8-nonadienoate, respectively, with E-stereoisomeric purity of not less than 98% in the directed synthesis of mono- and diene components of the acetogenin and macrolide structure of a number of pheromones of economically important harmful insects of the orders Lepidoptera and Coleoptera (sex pheromone of Mediterranean fruit fly Ceratitis capitata, fruit-tree leafroller moth Archips argyrospilus and meadow moth Loxostege sticticalis, Hessian fly Mayetiola destructor, beet moth Scrobipalpa ocellatella, European grapevine moth Lobesia botrana, of females lackey moth Malocosoma neustra L., silkworm Bombyx mori, currant borer moths Synanthedon tipuliformis and wood leopard moth Zeuzera pyrina, the melon fly Dacus cucurbitae, the peach twig borer moths Anarsia lineatella, the turnip moth Agrotis segetum) and 9-oxo-2E-decenoic acid – the multifunctional queen pheromone of the honeybee Apis mellifera L., using at key stages reactions of hydride reduction, hydroboration- or hydroalumination-oxidation, catalyzed cross-coupling, Wittig olefination, etc.

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Takanashi, Shin-Ichi, and Kenji Mori. "Pheromone Synthesis, CLXXIX. Synthesis of Lurlenic Acid and Lurlenol, the Sex Pheromones of the Green FlagellateChlamydomonas." Liebigs Annalen 1997, no. 5 (1997): 825–38. http://dx.doi.org/10.1002/jlac.199719970507.

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42

Buehrer, B. M., and B. Errede. "Coordination of the mating and cell integrity mitogen-activated protein kinase pathways in Saccharomyces cerevisiae." Molecular and Cellular Biology 17, no. 11 (1997): 6517–25. http://dx.doi.org/10.1128/mcb.17.11.6517.

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Mating pheromone stimulates a mitogen-activated protein (MAP) kinase activation pathway in Saccharomyces cerevisiae that induces cells to differentiate and form projections oriented toward the gradient of pheromone secreted by a mating partner. The polarized growth of mating projections involves new cell wall synthesis, a process that relies on activation of the cell integrity MAP kinase, Mpk1. In this report, we show that Mpk1 activation during pheromone induction requires the transcriptional output of the mating pathway and protein synthesis. Consequently, Mpk1 activation occurs subsequent to the activation of the mating pathway MAP kinase cascade. Additionally, Spa2 and Bni1, a formin family member, are two coil-coil-related proteins that are involved in the timing and other aspects of mating projection formation. Both proteins also affect the timing and extent of Mpk1 activation. This correlation suggests that projection formation comprises part of the pheromone-induced signal that coordinates Mpk1 activation with mating differentiation. Stimulation of Mpk1 activity occurs through the cell integrity phosphorylation cascade and depends on Pkc1 and the redundant MAP/Erk kinases (MEKs), Mkk1 and Mkk2. Surprisingly, Mpk1 activation by pheromone was only partially impaired in cells lacking the MEK kinase Bck1. This Bck1-independent mechanism reveals the existence of an alternative activator of Mkk1/Mkk2 in some strain backgrounds that at least functions under pheromone-induced conditions.

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43

Hoskovec, Michal, David Šaman, and Bohumír Koutek. "A convenient synthesis of 2,13- and 3,13-octadecadienyl acetates, sex pheromone components of the Synanthedon species." Collection of Czechoslovak Chemical Communications 55, no. 9 (1990): 2270–81. http://dx.doi.org/10.1135/cccc19902270.

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The sex pheromone components of several Synanthedon species, 2,13- and 3,13-octadecadienyl acetates (Ic, Id, IIc, IId), have been synthesized following the acetylenic route of chain elongation. Starting from ω-alkyn-1-ols III, the final compounds were constructed in five steps in about 30% overall yields. Transformation of triple bond containing intermediates into the corresponding (Z)- and (E)-olefins was achieved either by hydrogenation over the P2-Ni catalyst or by using a dispersion of sodium in toluene. The title pheromones were generated in more than 97% stereoisomeric purity. 1H and 13C NMR data of all derivatives are included.

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44

Francke, Wittko, Stephan Franke, Jan Bergmann, et al. "Female Sex Pheromone of Cameraria ohridella Desch. and Dim. (Lepidoptera: Gracillariidae): Structure Confirmation, Synthesis and Biological Activity of (8E,10Z)-8,10-tetradecadienal and Some Analogues." Zeitschrift für Naturforschung C 57, no. 7-8 (2002): 739–52. http://dx.doi.org/10.1515/znc-2002-7-832.

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Mass spectrometric investigations confirmed the structure of the female produced sex pheromone of the horse-chestnut leafminer Cameraria ohridella Desch. and Dim. to be (8E,10Z)-8,10-tetradecadienal. Pure samples, prepared in a straightforward synthesis, were highly attractive in field tests and proved to be suitable for monitoring of flight activities and population dynamics. In mixtures with the synthetic pheromone, analogues like 9-tridecynal and 7-dodecynyl formate were shown to reduce trap catches. In electroantennographic experiments, pheromone analogues were less active than the pheromone. 9-Tridecynal was the most EAG active analogue tested, followed by 7-dodecyn-1-yl formate and 7-undecyn-1- yl formate.

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45

Kukovinets, O. S., T. I. Zvereva, V. G. Kasradze, et al. "Novel synthesis of Planococcus citri pheromone." Chemistry of Natural Compounds 42, no. 2 (2006): 216–18. http://dx.doi.org/10.1007/s10600-006-0082-x.

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46

Guangzhong, Guo, Li Zhenyu, Lin Guoqiang, et al. "Identification and synthesis of insect pheromone." Journal of Chemical Ecology 16, no. 3 (1990): 819–26. http://dx.doi.org/10.1007/bf01016492.

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47

Mori, Kenji, and Takuya Tashiro. "Useful Reactions in Modern Pheromone Synthesis." Current Organic Synthesis 1, no. 1 (2004): 11–29. http://dx.doi.org/10.2174/1570179043485466.

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48

SENDA, Shuji, and Kenji MORI. "Pheromone synthesis. Part 99. Synthesis of (-)-invictolide, the pheromone component of the red imported fire ant." Agricultural and Biological Chemistry 51, no. 5 (1987): 1379–84. http://dx.doi.org/10.1271/bbb1961.51.1379.

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49

Yanarateş, Erkan, Yılmaz Yıldırır, and Ali Dişli. "Synthesis of some new derivatives of tick pheromones and investigation of pheromone properties." Biological Diversity and Conservation 12, no. 3 (2019): 132–43. http://dx.doi.org/10.5505/biodicon.2019.43043.

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50

Zhang, D., X. Liu, MA Harley, and JD Hardege. "Uridine-5’-tri-phosphate is a candidate component of the soluble sex pheromone bouquet in a marine shrimp, Lysmata wurdemanni." Marine Ecology Progress Series 640 (April 23, 2020): 139–46. http://dx.doi.org/10.3354/meps13294.

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Characterisation of distance sex pheromones in decapods is challenging, although great efforts have been made in this field in the past 50 yr. In a previous study, we identified a component of the distance (soluble) sex pheromone bouquet of the peppermint shrimp Lysmata wurdemanni as being a uridine-5’-di-phosphate (UDP)-like chemical. However, UDP itself does not elicit the full pre-copulatory ‘approach and follow’ behaviour in peppermint shrimp. Here, we tested the hypothesis that the UDP-like chemical is uridine-5’-tri-phosphate (UTP), a metabolic product of chitin synthesis, and that this is the component of the distance sex pheromone of L. wurdemanni. We ran a series of bioassays to examine whether UDP, UTP or mixtures of the 2 compounds elicit male mating behaviour. Our results showed that male L. wurdemanni responded to UTP by displaying stereotyped courtship behaviour—the same behaviour elicited from males when exposed to water that previously contained moulting females. Combining UTP and UDP did not enhance the intensity of this courtship behaviour. The minimum effective concentration of UTP found to elicit courtship behaviour in the male shrimp was between 10-6 and 10-7 M. HPLC analysis showed the presence of UTP in the moulting water of female shrimp and also the partial conversion of UTP to UDP during the sample preparation procedure. Both the bioassay and chemical analysis results presented in this study suggest that UTP is a component of the distance sex pheromone in L. wurdemanni, and that the major peak in the chromatogram of a L. wurdemanni pheromone identified in previous studies might be a breakdown product of UTP.

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