Experimental evaluation and structure–activity relationship analysis of bridged-ring terpenoid derivatives as novel Blattella germanica repellent

References

• M.R. Fakoorziba, F. Eghbal, J. Hassanzadeh, and M.D. Moemenbellah-Fard, Cockroaches (Periplaneta americana and Blattella germanica) as potential vectors of the pathogenic bacteria found in nosocomial infections, Ann. Trop. Med. Parasitol. 104 (2010), pp. 521–528. doi:10.1179/136485910X12786389891326.
   PubMed Web of Science ®Google Scholar
• A. Sheih, W.C. Parks, and S.F. Ziegler, GM-CSF produced by the airway epithelium is required for sensitization to cockroach allergen, Mucosal. Immunol. 10 (2017), pp. 705–715. doi:10.1038/mi.2016.90.
   PubMed Web of Science ®Google Scholar
• Z. Wen and J.G. Scott, Cross-resistance to imidacloprid in strains of German cockroach (Blattella germanica) and house fly (Musca domestica), Pestic. Sci. 49 (1997), pp. 367–371. doi:10.1002/(SICI)1096-9063(199704)49:4<367::AID-PS542>3.0.CO;2-L.
   Google Scholar
• S.M. Valles and R.J. Brenner, Variation in hydramethylnon susceptibility among insecticide-resistant German cockroaches (Blattodea: Blattellidae), J. Econ. Entomol. 92 (1999), pp. 617–623. doi:10.1093/jee/92.3.617.
   Web of Science ®Google Scholar
• A. Salehzadeh, Z. Darvish, and Z. Darvish, The efficacy of baits containing abamectin, dinotefuran, imidacloprid and pyriproxyfen+abamectin against (Blattella germanica L.) (Blattaria: Blattellidae), the German cockroach, Afr. Entomol. 28 (2020), pp. 225–237. doi:10.4001/003.028.0225.
   Web of Science ®Google Scholar
• D.D. Biehler, Pests in the City: Flies, Bedbugs, Cockroaches, and Rats, University of Washington Press, Washington, 2013.
   Google Scholar
• M. Debboun and D. Strickman, Insect repellents and associated personal protection for a reduction in human disease, Med. Vet. Entomol. 27 (2013), pp. 1–9. doi:10.1111/j.1365-2915.2012.01020.x.
   PubMed Web of Science ®Google Scholar
• J.H. Diaz, Chemical and plant-based insect repellents: Efficacy, safety, and toxicity, Wild. Environ. Med. 27 (2016), pp. 153–163. doi:10.1016/j.wem.2015.11.007.
   PubMed Web of Science ®Google Scholar
• Z. Syed and W.S. Leal, Mosquitoes smell and avoid the insect repellent DEET, Proc. Nat. Acad. Sci. 105 (2008), pp. 13598–13603. doi:10.1073/pnas.0805312105.
   PubMed Web of Science ®Google Scholar
• E.N. Weeks, G. Wasserberg, J.L. Logan, J. Agneessens, S.A. Stewart, and S. Dewhirst, Efficacy of the insect repellent IR3535 on the sand fly Phlebotomus papatasi in human volunteers, J. Vector. Ecol. 44 (2019), pp. 290–292. doi:10.1111/jvec.12362.
   PubMed Web of Science ®Google Scholar
• K. Karunamoorthi and S. Sabesan, Laboratory evaluation of dimethyl phthalate treated wristbands against three predominant mosquito (Diptera: Culicidae) vectors of disease, Eur. Rev. Med. Pharmacol. 14 (2010), pp. 443–448.
   PubMed Web of Science ®Google Scholar
• K. Huang, D. Zhang, J. Ren, R. Dong, and H. Wu, Screening of the repellent activity of 12 essential oils against adult German cockroach (Dictyoptera: Blattellidae): Preparation of a sustained release repellent agent of binary oil-γ-cd and its repellency in a small container, J. Econ. Entomol. 113 (2020), pp. 2171–2178. doi:10.1093/jee/toaa162.
   PubMed Web of Science ®Google Scholar
• C. Yoon, S.H. Kang, J.O. Yang, D.J. Noh, P. Indiragandhi, and G.H. Kim, Repellent activity of citrus oils against the cockroaches Blattella germanica, Periplaneta americana and P. fuliginosa, J. Pestic. Sci. 34 (2009), pp. 77–88. doi:10.1584/jpestics.G07-30.
   Web of Science ®Google Scholar
• H.R. Lee, G.H. Kim, W.S. Choi, and I.K. Park, Repellent activity of Apiaceae plant essential oils and their constituents against adult German cockroaches, J. Econ. Entomol. 110 (2017), pp. 552–557. doi:10.1093/jee/tow290.
   PubMed Web of Science ®Google Scholar
• U. Thavara, A. Tawatsin, P. Bhakdeenuan, P. Wongsinkongman, T. Boonruad, and J. Bansiddhi, Repellent activity of essential oils against cockroaches (dictyoptera: Blattidae, blattellidae, and blaberidae) in Thailand, Se. Asian. J. Trop Med. 38 (2007), pp. 663–673. https://www.tm.mahidol.ac.th/seameo/2007_38_4/10-4056.pdf.
   PubMedGoogle Scholar
• R. Rahayu, A. Darmis, and R. Jannatan, Potency of Papaya Leaf (Carica papaya L.) as toxicant and repellent against German cockroach (Blattella germanica L.), Pak, Pak. J. Biol. Sci. 23 (2020), pp. 126–131. doi:10.3923/pjbs.2020.126.1311.
   PubMedGoogle Scholar
• Z.L. Liu, M. Yu, and X.M. Li, Repellent activity of eight essential oils of Chinese medicinal herbs to Blattella germanica L, Rec, Nat. Prod. 5 (2011), pp. 176–183. https://www.acgpubs.org/doc/2018080616271423-RNP-1006-252.pdf.
   Google Scholar
• P.J. Robbins and M.G. Cherniack, Review of the biodistribution and toxicity of the insect repellent N,N -diethyl- m -toluamide (DEET), J. Toxicol. Env. Health A 18 (1986), pp. 503–525. doi:10.1080/15287398609530891.
   PubMed Web of Science ®Google Scholar
• M.S. Fradin, Mosquitoes and mosquito repellents: A clinician’s guide, Ann. Intern. Med. 128 (1998), pp. 931–940. doi:10.7326/0003-4819-128-11-199806010-00013.
   PubMed Web of Science ®Google Scholar
• G. Koren, D. Matsui, and B. Bailey, DEET-based insect repellents: Safety implications for children and pregnant and lactating women, Can. Med. Assoc. J. 169 (2003), pp. 209–212. doi:10.3906/biy-1412-88.
   PubMed Web of Science ®Google Scholar
• S.L. Liao, Y. Liu, and H.Y. Si, Hydronopylformamides: Modification of the naturally occurring compound (-)-β-pinene to produce insect repellent candidates against Blattella germanica, Molecules 22 (2017), pp. 1004. doi:10.3390/molecules22061004.
   PubMed Web of Science ®Google Scholar
• V.V. Costa, H. Bayahia, and E.F. Kozhevnikova, Highly active and recyclable metal oxide catalysts for the Prins condensation of biorenewable feedstocks, Chem. Cat. Chem. 6 (2014), pp. 2134–2139. doi:10.1002/cctc.201402160.
   Google Scholar
• L.H. Zhao, Z.Q. Xiao, J.Z. Chen, and Z.D. Wang, A study on synthesis of hydronopol (in Chinese), Chem. World. 53 (2012), pp. 163–168. doi:10.19500/j.cnki.0367-6358.2012.03.011.
   Google Scholar
• L.H. Zhao, X.L. Liu, Z.Q. Xiao, J.Z. Chen, and Z.D. Wang, The synthesis and structural analysis for hydronopol and its carboxylic ethers, J. Jiangxi Normal Uni. (Nat. Sci. Ed.) (in Chinese). 36 (2012), pp. 12–15. doi:10.16357/j.cnki.1000-5862.2012.01.004.
   Google Scholar
• L.H. Zhao, Z.Q. Xiao, J.Z. Chen, Z.D. Wang, G.R. Fan, and S.X. Chen, Synthesis and structural analysis of hydronopol and its halides (in Chinese), Chem. Ind. For. Prod. 32 (2012), pp. 39–42.
   Google Scholar
• L.H. Zhao, X.L. Liu, Z.Q. Xiao, J.Z. Chen, and Z.D. Wang, Synthesis and identification of hydronopol and its alkyl ethers (in Chinese), Chem. Res. Appl. 24 (2012), pp. 123–126.
   Google Scholar
• L.H. Zhao, X.L. Liu, Z.Q. Xiao, J.Z. Chen, and Z.D. Wang, Synthesis of hydronopoic acid and its acid amide (in Chinese, Chem. Res. Appl. 25 (2013), pp. 245–248.
   Google Scholar
• Y. Liu, Z.Q. Xiao, P.Y. Lu, J.Z. Chen, Z.D. Wang, and G.R. Fan, Synthesis and structural analysis of hydronopyl formic acid and its esters (in Chinese, Chem. Ind. For. Prod. 33 (2013), pp. 57–61.
   Google Scholar
• M.J. Frisch, G.W. Trucks, and H.B. Schlegel, Gaussian 09, Gaussian. Inc., Wallingford, 2009.
   Google Scholar
• R. Dennington, T. Keith, and J. Millam, Gaussview. Version5, Semichem. Inc, Shawnee Mission, 2009.
   Google Scholar
• M.J.S. Dewar, A.J. Holder, R.D. Dennington, I.D.A. Liotard, D.G. Truhlar, T.A. Keith, J.M. Millam, and C.D. Harris, AMPAC 8 User Manual, Semichem, Inc, Shawnee, 2004.
   Google Scholar
• Z.D. Wang, J. Song, J. Chen, Z. Song, S. Shang, and Z. Jiang, QSAR study of mosquito repellents from terpenoid with a six-member-ring, Bioorg. Med. Chem. Lett. 18 (2008), pp. 2854–2859. doi:10.1016/j.bmcl.2008.03.091.
   PubMed Web of Science ®Google Scholar
• S.L. Liao, J. Song, Z.D. Wang, J. Chen, G. Fan, and Z.Q. Song, Molecular interactions between terpenoid mosquito repellents and human-secreted attractants, Bioorg. Med. Chem. Lett. 24 (2014), pp. 773–779. doi:10.1016/j.bmcl.2013.12.102.
   PubMed Web of Science ®Google Scholar
• P. Ruiz, G. Begluitti, T. Tincher, J. Wheeler, and M. Mumtaz, Prediction of acute mammalian toxicity using QSAR methods: A case study of sulfur mustard and its breakdown products, Molecules 17 (2012), pp. 8982–9001. doi:10.3390/molecules17088982.
   PubMed Web of Science ®Google Scholar
• J. Devillers and H. Devillers, Prediction of acute mammalian toxicity from QSARs and interspecies correlations, SAR QSAR Environ. Res. 20 (2009), pp. 467–500. doi:10.1080/10629360903278651.
   PubMed Web of Science ®Google Scholar
• A.R. Katritzky, D.A. Dobchev, I. Tulp, M. Karelson, and D.A. Carlson, QSAR study of mosquito repellents using Codessa Pro, Bioorg. Med. Chem. Lett. 16 (2006), pp. 2306–2311. doi:10.1016/j.bmcl.2005.11.113.
   PubMed Web of Science ®Google Scholar
• J. Devillers, V. Sartor, and H. Devillers, Predicting mosquito repellents for clothing application from molecular fingerprint-based artificial neural network SAR models, SAR QSAR Environ. Res. 33 (2022), pp. 729–751. doi:10.1080/1062936X.2022.2124014.
   PubMed Web of Science ®Google Scholar
• J. Devillers, V. Sartor, J.P. Doucet, A. Doucet-Panaye, and H. Devillers, In silico prediction of mosquito repellents for clothing application, SAR QSAR Environ. Res. 33 (2022), pp. 239–257. doi:10.1080/1062936X.2022.2062871.
   PubMed Web of Science ®Google Scholar
• J. Song, Z.D. Wang, F. Alexander, J.Z. Han, and Z.K. Jiang, Terpenoid mosquito repellents: A combined DFT and QSAR study, Bioorg. Med. Chem. Lett. 23 (2013), pp. 1245–1248. doi:10.1016/j.bmcl.2013.01.015.
   PubMed Web of Science ®Google Scholar
• A.R. Katritzky, V. Lobanov, and M. Karelson, CODESSA: Reference Manual, University of Florida, Florida, 1994.
   Google Scholar
• A.R. Katritzky, R. Petrukhin, H. Yang, and M. Karelson, CODESSA PRO User’s Manual, University of Florida, Florida, 2002.
   Google Scholar
• H. Liu, X. Yao, and M. Liu, Prediction of gas-phase reduced ion mobility constants (K0) based on the multiple linear regression and projection pursuitregression, Talanta 71 (2007), pp. 258–263. doi:10.1016/j.talanta.2006.03.058.
   PubMed Web of Science ®Google Scholar
• D.T. Stanton and P.C. Jurs, Charged Partial Surface-Area Descriptors for Structure-Property Relationship Studies, Papers of the american chemical society, Washington, 1990.
   Google Scholar
• A.R. Katritzky, V.S. Lobanov, and M. Karelson, Comprehensive descriptors for structural and statistical analysis. 1: Correlations between structure and physical properties of substituted pyridines, Rev. Roum. Chim. 41 (1996), pp. 851–867.
   Web of Science ®Google Scholar