Review on stored grain insect pheromones

Akasaka K, Tamogami S, Beeman RW, Mori K. 2011. Pheromone synthesis. Part 245: Synthesis and chromatographic analysis of the four stereoisomers of 4,8-dimethyldecanal, the male aggregation pheromone of the red flour beetle, Tribolium castaneum. Tetrahedron 67(1).

Arthur FH, Campbell JF, Toews MD. 2014. Distribution, abundance, and seasonal patterns of stored product beetles in a commercial food storage facility. Journal of Stored Products Research 56.

Ashworth JR. 1993. The biology of Lasioderma serricorne. Journal of Stored Products Research 29(4).

Athanassiou CG, Kavallieratos NG, Trematerra P. 2006. Responses of Sitophilus oryzae (Coleoptera: Curculionidae) and Tribolium confusum (Coleoptera: Tenebrionidae) to traps baited with pheromones and food volatiles. European Journal of Entomology 103(2). https://doi.org /10.14411/eje.2006.050

Awater-Salendo S, Schulz H, Hilker M, Fürstenau B. 2020. The Importance of Methyl-Branched Cuticular Hydrocarbons for Successful Host Recognition by the Larval Ectoparasitoid Holepyris sylvanidis. Journal of Chemical Ecology 46(11-12). https://doi.org/10.1007/s10886-020-01227-w

Badanyan SO, Makaryan GM, Ovanesyan AL, Panosyan GA. 2001. (2E)-4,4-dimethoxy-2-butenal in the synthesis of conjugated dienes and dienals. Russian Journal of Organic Chemistry 37(5). https://doi.org/10.1023/A:1012479213224

Bandara HMDS, Wijayaratne LKW, Egodawatta WCP, Morrison WR. 2021. Orientation of Tribolium castaneum (Coleoptera: Tenebrionidae) adults to 4,8-dimethyldecanal, kairomone and botanical oils following ambient, low, or high temperature exposure. Journal of Stored Products Research, 94, 101893. https://doi.org

Barak A V, Burkholder WE. 1985. A versatile and effective trap for detecting and monitoring stored-product coleoptera. Agriculture, Ecosystems & Environment 12(3). https://doi.org/https://doi.org

Barak AV, Burkholder WE, Faustini DL. 1990. Factors Affecting the Design of Traps for Stored-Product Insects. Journal of the Kansas Entomological Society 63(4), 466-485.

Birkinshaw LA, Hodges RJ, Addo S. 2004. Flight behaviour of Prostephanus truncatus and Teretrius nigrescens demonstrated by a cheap and simple pheromone-baited trap designed to segregate catches with time. Journal of Stored Products Research 40(2). https://doi.org/10.1016/S0022-474X(02)00094-2

Bloch Qazi MC, Boake CRB, Lewis SM. 1998. The femoral setiferous glands of Tribolium castaneum males and production of the pheromone 4,8-dimethyldecanal. Entomologia Experimentalis et Applicata, 89(3). https://doi.org/10.1046/j.1570-7458.1998.00414.x

Boake CR. 1985. Genetic consequences of mate choice: a quantitative genetic method for testing sexual selection theory. Science (New York, N.Y.) 227(4690). https://doi.org/10.1126/science.227.46

Buckman KA, Campbell JF. 2013. How varying pest and trap densities affect Tribolium castaneum capture in pheromone traps. Entomologia Experimentalis et Applicata 146(3). https://doi.org/ 10.1111/eea.12039

Burkholder WE, Boush GM. 1974. Pheromones in Stored Product Insect Trapping and Pathogen Dissemination. EPPO Bulletin 4(4). https://doi.org/ 10.1111/j.1365-2338.1974.tb02393.x

Butenandt A, Beckmann R, Hecker E. 1961. Über den Sexuallockstoff des Seidenspinners, I: Der biologische Test und die Isolierung des reinen Sexuallockstoffes Bombykol. Hoppe-Seyler’s Zeitschrift Fur Physiologische Chemie 324(1). https://doi.org/10.1515/bchm2.1961.324.1.71

Campbell JF, Arbogast RT. 2004. Stored-product insects in a flour mill: Population dynamics and response to fumigation treatments. Entomologia Experimentalis et Applicata 112(3).

Campbell JF, Mullen MA, Dowdy AK. 2002. Monitoring stored product pests in food processing plants with pheromone trapping, contour mapping, and mark recapture. Journal of Economic Entomology, 95(5). https://doi.org/10.1603/0022-0

Campbell JF, Mullen MA. 2004 Distribution and dispersal behavior of Trogoderma variabile and Plodia interpunctella outside a food processing plant. Journal of Economic Entomology 97(4).

Campbell JF. 2012. Attraction of walking Tribolium castaneum adults to traps. Journal of Stored Products Research 51. https://doi.org/10.1016 /j.jspr.2012.

Campbell JF. 2013. Influence of landscape pattern in flour residue amount and distribution on Tribolium castaneum (Herbst) response to traps baited with pheromone and kairomone. Journal of Stored Products Research 52. https://doi.org/

Campos M, Phillips TW. 2013. Laboratory evaluation of attract-and-kill formulations against the Indianmeal moth, Plodia interpunctella (Hübner) (Lepidoptera: Pyralidae). Journal of Stored Products Research 52. https://doi.org/10.1016/j.jspr.

Campos M, Phillips TW. 2014. Attract-and-kill and other pheromone-based methods to suppress populations of the Indianmeal moth (Lepidoptera: Pyralidae). Journal of Economic Entomology 107(1). https://doi.org/10.1603/EC13451

Carvalho MO, Faro A, Subramanyam B. 2013. Insect population distribution and density estimates in a large rice mill in Portugal – A pilot study. Journal of Stored Products Research 52.

Castañé C, Agustí N, Estal P del, Riudavets J. 2020. Survey of Trogoderma spp. in Spanish mills and warehouses. Journal of Stored Products Research 88. https://doi.org/10.1016/j.jspr.2020.101661

Chambers J, Morgan CP, White PR, Mori K, Finnegan DE, Pinniger DB. 1990. Rust-red grain beetle,Cryptolestes ferrugineus, and flat grain beetle,Cryptolestes pusillus: Antennal and behavioral responses to synthetic components of their aggregation pheromones. Journal of Chemical Ecology 16(12). https://doi.org/10.1007/ BF00

Chambers J, Van Wyk CB, White PR, Gerrard CM, Mori K. 1996. Grain weevil,Sitophilus granarius (L.): Antennal and behavioral responses to male-produced volatiles. Journal of Chemical Ecology 22(9). https://doi.org/10.1007/BF02272404

Cheskis BA, Lebedeva KV, Moiseenkov AM. 1988. Effective synthesis of (4R,8R)- and (4R,8S)-enantiomers of 4,8-dimethyldecanal, the aggregation pheromone of the beatles Tribolium confusum and Tribolium castaneum. Institute of Organic Chemistry 4, 865-871.

Cheskis BA, Moiseenkov AM, Shpiro NA, Stashina GA, Zhulin VM. 1990a. Stereochemically controlled synthesis of racemic sitophilate, the aggregational pheromone of the grain weevil. Bulletin of the Academy of Sciences of the USSR Division of Chemical Science 39(4). https://doi.org/10.1007 /BF00960333

Cheskis BA, Shpiro NA, Moiseenkov AM. 1990b. Synthesis of ferrulactone I and its dimer. Bulletin of the Academy of Sciences of the USSR Division of Chemical Science 38(11). https://doi.org/10.1007/BF01168095

Cheskis BA, Shpiro NA, Moiseenkov AM. 1993. Effective synthesis of femrrulactone II based on the use of 2-carhoxyethyltriphenylphosphonium bromide. Russian Chemical Bulletin 42(4). https://doi.org/10.1007/BF00704022

Chiluwal K, Kim J, Bae S Do, Maharjan R, Park CG. 2017. Attractiveness of male azuki bean beetle to the synthetic blends of 2E- and 2Z-homofarnesals. Journal of Asia-Pacific Entomology 20(4). https://doi.org/10.1016/j.aspen.2017.09.003

Chiluwal K, Kim J, Bae S Do, Roh GH, Park CG. 2018. Methyl salicylate and trans-anethole affect the pheromonal activity of homofarnesal, the female sex pheromone of azuki bean beetle. Entomological Research 48(5). https://doi.org/10.1111/1748-

Collins LE, Bryning GP, Wakefield ME, Chambers J, Cox PD. 2007. Progress towards a multi-species lure: Identification of components of food volatiles as attractants for three storage beetles. Journal of Stored Products Research 43(1). https://doi.org /10.1016/j.jspr.2005.10.001

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Cork A, Hall DR, Hodges RJ, Pickett JA. 1991. Identification of major component of male-produced aggregation pheromone of larger grain borer, Prostephanus truncatus (Horn) (Coleoptera: Bostrichidae). Journal of Chemical Ecology 17(4).

Czeskis BA, Shpiro NA, Moiseenkovt AM. 1993. Efficient Synthesis of (S,Z)-Dodec-3-en-11 -olide (Ferrulactone II) using 2-Carboxyethyltriphenylphosphonium Bromide. Mendeleev Communications 3(3). https://doi.org /10.1070/MC1993v003n03ABEH000239

Daglish GJ, Ridley AW, Reid R, Walter GH. 2017. Testing the consistency of spatio-temporal patterns of flight activity in the stored grain beetles Tribolium castaneum (Herbst) and Rhyzopertha dominica (F.). Journal of Stored Products Research 72. https://doi.org/10.1016/j.jspr.2017.03.005

de Souza VN, de Oliveira CRF, Matos CHC, de Almeida DKF. 2016. Fumigation toxicity of essential oils against Rhyzopertha dominica (F.) in stored maize grain. Revista Caatinga 29(2). https://doi.org/10.1590/1983-21252016v29n220rc

Dissanayaka DMSK, Sammani AMP, Wijayaratne LKW, Bamunuarachchige TC, Morrison WR. 2020c. Distance and height of attraction by walking and flying beetles to traps with simultaneous use of the aggregation pheromones from Tribolium castaneum (Herbst) (Coleoptera: Tenebrionidae) and Rhyzopertha dominica (F.) (Coleoptera: Bostrychidae). Journal of Stored Products Research 89.

Dissanayaka DMSK, Sammani AMP, Wijayaratne LKW, Rajapakse RHS, Hettiarachchi S, Morrison WR. 2020d. Effects of aggregation pheromone concentration and distance on the trapping of Rhyzopertha dominica (F.) (Coleoptera: Bostrychidae) adults. Journal of Stored Products Research 88. https://doi.org/ 10.1016/j.jspr.2020.101657

Dissanayaka DMSK, Sammani AMP, Wijayaratne LKW. 2018a. Food oils as kairomones for trapping Tribolium castaneum (Herbst) (Coleoptera: Tenebrionidae) adults. Journal of Stored Products Research 79. https://doi.org /10.1016 /j.jspr.2018.09.005

Dissanayaka DMSK, Sammani AMP, Wijayaratne LKW. 2018b. Aggregation pheromone 4,8-dimethyldecanal and kairomone affect the orientation of Tribolium castaneum (Herbst) (Coleoptera: Tenebrionidae) adults. Journal of Stored Products Research 79. https://doi.org /10.1016 /j.jspr.2018.07.005

Dissanayaka DMSK, Sammani AMP, Wijayaratne LKW. 2020a. Orientation of Tribolium castaneum (Herbst) (Coleoptera: Tenebrionidae) adults at various distances to different concentrations of aggregation pheromone 4,8-dimethyldecanal. Journal of Stored Products Research 87. https://doi.org/10.1016/j.jspr. 2020.

Dissanayaka DMSK, Sammani AMP, Wijayaratne LKW. 2020b. Response of different population sizes to traps and effect of spinosad on the trap catch and progeny adult emergence in Tribolium castaneum (Herbst) (Coleoptera: Tenebrionidae). Journal of Stored Products Research 86. https://doi.org/10.1016/j.jspr.2020.101576

Doud CW, Cuperus GW, Kenkel P, Payton ME, Phillips TW. 2021. Trapping Tribolium castaneum (Coleoptera: Tenebrionidae) and other beetles in flourmills: Evaluating fumigation efficacy and estimating population density. Insects 12(2). https://doi.org/10.3390/insects12020144

Dowdy AK, Howard RW, Seitz LM, McGaughey WH. 1993. Response of Rhyzopertha dominica (Coleoptera, Bostrichidae) to its aggregation pheromone and wheat volatiles. Environmental Entomology, 22(5). https://doi.org /10.1093 /ee/22.5.965

Dowdy AK, Mullen MA. 1998. Multiple store-product insect pheromone use in pitfall traps. Journal of Stored Products Research 34(1). https://doi.org /10.1016/S0022-474X(97)00018-0

Dowell FE, Dowell CN. 2017. Reducing grain storage losses in developing countries. Quality Assurance and Safety of Crops and Foods 9(1). https://doi.org/10.3920/QAS2016.0897

Duehl AJ, Arbogast RT, Teal PE. 2011. Age and sex related responsiveness of Tribolium castaneum (Coleoptera: Tenebrionidae) in novel behavioral bioassays. Environmental Entomology 40(1). https://doi.org/10.1603/EN10107

Edde PA, Phillips TW, Nansen C, Payton ME. 2006. Flight activity of the lesser grain borer, Rhyzopertha dominica F. (Coleoptera: Bostrichidae), in relation to weather. Environmental Entomology 35(3). https://doi.org/10.1603/0046-225X-35.3.616

Edde PA, Phillips TW, Toews MD. 2005. Responses of Rhyzopertha dominica (Coleoptera: Bostrichidae) to its aggregation pheromones as influenced by trap design, trap height, and habitat. Environmental Entomology 34(6). https://doi.org /10.1603/0046-225X-34.6.1549

Eiras AE, Mafra-Neto A. 2001. Olfatometria aplicada ao estudo do comportamento de insetos. Feromônios de Insetos: Biologia, Química e Emprego No Manejo de Pragas. Ribeirão Preto, Editora Holos 206p, 27-39.

El-Sayed AM, Suckling DM, Wearing CH, Byers JA. 2006. Potential of mass trapping for long-term pest management and eradication of invasive species. In Journal of Economic Entomology 99(5). https://doi.org/10.1093/jee/99.5.1550

EMBRAPA. 2021. Brazilian Agricultura Research Corporation Origin and History of Soy in Brazil. Embrapa Soy. https://www.embrapa.br/en/ soja

Fadamiro HY, Gudrups I, Hodges RJ. 1998. Upwind flight of Prostephanus truncatus is mediated by aggregation pheromone but not food volatiles. Journal of Stored Products Research 34(2–3). https://doi.org/10.1016/S0022-474X(97)00044-1

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Fardisi M, Mason LJ. 2013. Influence of lure (food/sex pheromone) on young mated cigarette beetle (Lasioderma serricorne (F.)) (Coleoptera: Anobiidae) flight initiation. Journal of Stored Products Research 53.

Fargo WS, Cuperus GW, Bonjour EL, Burkholder WE, Clary BL, Payton ME. 1994. Influence of probe trap type and attractants on the capture of four stored-grain Coleoptera. Journal of Stored Products Research 30(3).

Faustini DL, Burkholder WE, Laub RJ. 1981. Sexually dimorphic setiferous sex patch in the male red flour beetle,Tribolium castaneum (Herbst) (Coleoptera: Tenebrionidae): Site of aggregation pheromone production. Journal of Chemical Ecology 7(2). https://doi.org/10.1007/BF00995769

Faustini DL. 1982. Male-porduced aggregation pheromone of the maize weevil. Ecology 9(7), 831-841.

Fedina TY, Lewis SM. 2007. Effect of Tribolium castaneum (Coleoptera: Tenebrionidae) nutritional environment, sex, and mating status on response to commercial pheromone traps. Journal of Economic Entomology 100(6). https://doi.org/10.1603/0022-0493(2007)100[1924:eotcct]2.0.co;2

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Gerken AR, Scully ED, Campbell JF. 2018. Red Flour Beetle (Coleoptera: Tenebrionidae) Response to Volatile Cues Varies With Strain and Behavioral Assay. Environmental Entomology 47(5).

Hagstrum DW, Phillips TW, Cuperus G. 2012. Stored Product Protection. Kansas State University. K-State Research and Extension.

Hagstrum DW, Phillips TW. 2017. Evolution of Stored-Product Entomology: Protecting the World Food Supply. In Annual Review of Entomology 62. https://doi.org/10.1146/annurev-ento-031616-

Hagstrum DW, Subramanyam B. 2006. Fundamentals of stored-product entomology. In D. W. Hagstrum & B. B. T.-F. of S.-P. E. Subramanyam (Eds.), American Associate of Cereal Chemists International. pp. 3-22. AACC International Press. https://doi.org/https://doi.org/10.1016/B978-1-

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