Yeni Potansiyel Oksadiazol Türevlerinin Tetranychus urticae Koch (Prostigmata:Tetranychidae)'de Akarisidal Aktiveleri

Abstract

Tetranychus urticae Koch, 1836 (Prostigmata: Tetranychidae) birçok pestisite dayanıklılık gösterdiği rapor edilen kozmopolit bir türdür. Bu sorunu önleme yöntemlerinden biri yeni etken madde gruplarının keşfidir. Yeni etken madde keşfinin maliyet ve zaman açısından önemli dezavantajları olması araştırmacıları mevcut etken maddelerde değişiklik yapmaya yöneltmiştir. Etoxazole, bazı önemli zararlı akar türlerine karşı etkili olduğu bildirilen bir etken maddedir. Bu nedenle çeşitli maddelerle türevlendirme çalışmaları yapılmaktadır. Bu çalışmada, kimyasal yapıları değiştirilebilen oxidazole grubuna bağlı hedef moleküller, biyoizosterizm yaklaşımı kullanılarak oxazoline halkasının oksadiazole ile değiştirilmesi ve halkanın C-2 ve C-4 pozisyonlarına ikame edilmiş fenil halkaları eklenmesiyle tasarlanmıştır. Yedi etken maddenin (3a, 3b, 3c, 3d, 3e, 3f, 3g) T. urticae'nin nimf dönemleri üzerindeki toksik etkileri incelendiğinde, etoxazole uygulanan kontrol grubundan sonra sırasıyla en yüksek toksik etkiler %66, %64 ve %58 oranlarında 3b, 3a ve 3g etken maddelerinde tespit edilmiştir. Yumurta dönemindeki toksik etkiler incelendiğinde ise 3a grubunun benzer toksik etki gösterdiği, diğer etkin maddelerin ise nispeten daha düşük toksik etki gösterdiği belirlenmiştir. Sonuç olarak T. urticae'nin farklı dönemlerinde etkili olan oxidazole grubu bileşiklerin türevlerinin varlığı bu zararlının kontrolünde umut verici bir yaklaşım olarak görünmektedir.

Keywords

• Tetranychus urticae
• etoxazole
• oxadiazole
• akarisit

Acaricidal Activities of New Potential Oxadiazole Derivatives on Tetranychus urticae Koch (Prostigmata:Tetranychidae)

Abstract

Tetranychus urticae Koch, 1836 (Prostigmata: Tetranychidae) is a cosmopolitan species known for its resistance to many pesticides. One strategy to address this challenge is the discovery of new groups of active substances. However, the high cost and time required for discovering new molecules have prompted researchers to focus on modifying existing active substances. Etoxazole is an active ingredient reported to be effective against several economically important mite species. Therefore, derivatization studies have been carried out using this compound as a lead structure. In the present study, target molecules containing modifiable oxadiazole groups were designed through a bioisosterism approach, in which the oxazoline ring was replaced with an oxadiazole ring, and substituted phenyl groups were introduced at the C-2 and C-4 positions. When the toxic effects of seven synthesized active substances (3a, 3b, 3c, 3d, 3e, 3f, and 3g) were tested against the nymphal stages of T. urticae, the highest mortality rates were observed with compounds 3b, 3a, and 3g (66%, 64%, and 58%, respectively), following the etoxazole-treated control group. At the egg stage, compound 3a exhibited toxic effects comparable to etoxazole, whereas the remaining derivatives displayed relatively lower levels of activity. In conclusion, the findings indicate that derivatives of the oxadiazole group, showing stage-specific activity against T. urticae, represent a promising approach for the development of new control strategies against this pest.

Keywords

• Tetranychus urticae
• etoxazole
• oxadiazole
• acaricide

References

1. Agrawal A.A., 2000. Host‐range evolution: adaptation and trade‐offs in fitness of mites on alternative hosts. Ecology, 81 (2), 500-508.
2. Assouguem A., Kara M., Mechchate H., Korkmaz Y.B., Benmessaoud S., Ramzi A., Abdullah K.R., Noman O.M., Farah A., Lazraq A., 2022. Current situation of Tetranychus urticae (Acari: Tetranychidae) in Northern Africa: The sustainable control methods and priorities for future research. Sustainability, 14 (4), 2395.
3. Attia S., Grissa K.L., Lognay G., Bitume E., Hance T., Mailleux A.C., 2013. A review of the major biological approaches to control the worldwide pest Tetranychus urticae (Acari: Tetranychidae) with special reference to natural pesticides: Biological approaches to control Tetranychus urticae. Journal of Pest Science, 86 (3), 361-386.
4. Ay R., Sökeli E., Karaca I., Gürkan M.O., 2005. Response to some acaricides of the two-spotted spider mite (Tetranychus urticae Koch) from protected vegetables in Isparta. Turkish Journal of Agriculture and Forestry, 29 (3), 165-171.
5. Chen Y., Tian J., Tan Y., Liu Y., Wang Q., 2024. Design, synthesis, and acaricidal activity of 2, 5-Diphenyl-1, 3-oxazoline compounds. Molecules, 29 (17), 4149.
6. Chen S., Zhang Y., Liu Y., Wang Q., 2021. Highly efficient synthesis and acaricidal and insecticidal activities of novel oxazolines with N-heterocyclic substituents. Journal of Agricultural and Food Chemistry, 69 (12), 3601-3606.
7. Chen S., Zhang Y., Liu Y., Wang Q., 2019. Design, synthesis, acaricidal activities, and structure–activity relationship studies of novel oxazolines containing sulfonate moieties. Journal of Agricultural and Food Chemistry, 67 (49), 13544-13549.
8. Dai H., Chen J., Li G., Ge S., Shi Y., Fang Y., Ling Y., 2017. Design, synthesis, and bioactivities of novel oxadiazole-substituted pyrazole oximes. Bioorganic & Medicinal Chemistry Letters, 27 (4), 950-953.

9. Das S.K. 2016. Screening of bioactive compounds for development of new pesticides: a mini review. Universal Journal of Agricultural Research 4 (1), 15-20.
10. Denholm I., Rowland M.W., 1992. Tactics for managing pesticide resistance in arthropods: theory and practice. Annual Review of Entomology, 37, 91-112.
11. Grbić, M., Van Leeuwen T., Clark R.M., Rombauts S., Rouzé P., Grbić V., Osborne E.J., Dermauw W., Ngoc P.C.T., Ortego F., Hernández-Crespo P., Diaz I., Martinez M., Navajas M., Sucena E., Magalhães S., Nagy L., Pace R.M., Djuranović S., Smagghe G., Iga M., Christiaens O., Veenstra J.A., Ewer J., Mancilla Villalobos R., Hutter J.L., HudsonS.D., Velez M., Yi S.V., Zeng J., Pires-daSilva A., Roch F., Cazaux M., Navarro M., Zhurov V., Acevedo G., Bjelica A., Fawcett J.A., Bonnet E., Martens C., Baele G., Lothar Wissler L., Sanchez-Rodriguez A., Tirry L., Blais C., Demeestere K., Henz S.R., Gregory T.R., Mathieu J., Verdon L., Farinelli L., Schmutz J., Lindquist E., Feyereisen R., Van de Peer Y., 2011. The genome of Tetranychus urticae reveals herbivorous pest adaptations. Nature, 479 (7374), 487-492.
12. Jiang B., Jin X., Dong Y., Guo B., Cui L., Deng X., Zhang L., Yang Q., Li Y., Yang X., Smagghe G., 2020. Design, synthesis, and biological activity of novel heptacyclic pyrazolamide derivatives: a new candidate of dual-target insect growth regulators. Journal of Agricultural and Food Chemistry, 68 (23), 6347-6354.
13. Jutsum A.R., Heaney S.P., Perrin B.M., Wege P.J., 1998. Pesticide resistance: assessment of risk and the development and implementation of effective management strategies. Pesticide Science, 54 (4), 435-446.
14. Khanahmadi M., Pakravan P., Hemati A., Azandaryani M.N., Ghamari E., 2017. Fumigant toxicity of Artemisia haussknechtii essential oil and its nano-encapsulated form. Pharma, 2, 1776-1783.
15. Kim Y.J., Lee S.H., Lee S.W., Ahn Y.J., 2004. Fenpyroximate resistance in Tetranychus urticae (Acari: Tetranychidae): cross‐resistance and biochemical resistance mechanisms. Pest Management Science: formerly Pesticide Science, 60 (10), 1001-1006.
16. Li Y., Li C., Zheng Y., Wei X., Ma Q., Wei P., Ma Q., Wei P., Liu Y., Qin Y., Yang N., Sun Y., Ling Y., Yang X., Wang Q., 2014. Design, synthesis, acaricidal activity, and mechanism of oxazoline derivatives containing an oxime ether moiety. Journal of Agricultural and Food Chemistry, 62 (14), 3064-3072.
17. Li Y., Yang N., Wei X., Ling Y., Yang X., Wang Q., 2014. Evaluation of etoxazole against insects and acari in vegetables in China. Journal of Insect Science, 14 (1), 104.
18. Lima L.M., Barreiro E.J., 2005. Bioisosterism: a useful strategy for molecular modification and drug design. Current Medicinal Chemistry, 12 (1), 23-49.
19. Liu Q., Zhu R., Gao S., Ma S.H., Tang H.J., Yang J.J., Diao Y., Wang H., Zhu H.J., 2017. Structure‐based bioisosterism design, synthesis, insecticidal activity and structure–activity relationship (SAR) of anthranilic diamide analogues containing 1, 2, 4‐oxadiazole rings. Pest Management Science, 73 (5), 917-924.
20. Mermer A., Faiz O., Demirbas A., Demirbas N., Alagumuthu M., Arumugam S., 2019. Piperazine-azole-fluoroquinolone hybrids: Conventional and microwave irradiated synthesis, biological activity screening and molecular docking studies. Bioorganic Chemistry, 85, 308-318.
21. Nauen R., Smagghe G., 2006. Mode of action of etoxazole. Pest Management Science: formerly Pesticide Science, 62 (5), 379-382.
22. Opit, G.P., Nechols J.R., Margolies D.C., 2004. Biological control of twospotted spider mites, Tetranychus urticae Koch (Acari: Tetranychidae), using Phytoseiulus persimilis Athias-Henriot (Acari: Phytoseidae) on ivy geranium: assessment of predator release ratios. Biological Control, 29 (3), 445-452.
23. Ozdemir S.B., Demirbas N., Cebeci Y.U., Bayrak H., Mermer A., Ceylan S., DemirbasA., 2017. Synthesis and antimicrobial activities of hybrid heterocyclic molecules based on 1-(4-fluorophenyl) piperazine skeleton. Letters in Drug Design & Discovery, 14 (9), 1014-1034.
24. Patani G.A., LaVoie E.J., 1996. Bioisosterism: a rational approach in drug design. Chemical Reviews, 96 (8), 3147-3176.
25. Rincón R.A., Rodríguez D., Coy-Barrera E., 2019. Botanicals against Tetranychus urticae Koch under laboratory conditions: A survey of alternatives for controlling pest mites. Plants, 8 (8), 272.
26. Rioja C., Zhurov V., Bruinsma K., Grbic M., Grbic V., 2017. Plant-herbivore interactions: a case of an extreme generalist, the two-spotted spider mite Tetranychus urticae. Molecular Plant-Microbe Interactions, 30 (12), 935-945.
27. Romanov-Michailidis F., Rovis T., 2015. Natural polarity inverted. Nature, 523 (7561), 417-418.
28. Sato M.E., Da Silva M.Z., Raga A., Cangani K. G., Veronez B., Nicastro R.L., 2011. Spiromesifen toxicity to the spider mite Tetranychus urticae and selectivity to the predator Neoseiulus californicus. Phytoparasitica, 39 (5), 437-445.
29. Shao X., Fu H., Xu X., Xu X., Liu Z., Li Z., Qian X., 2010. Divalent and oxabridged neonicotinoids constructed by dialdehydes and nitromethylene analogues of imidacloprid: design, synthesis, crystal structure, and insecticidal activities. Journal of Agricultural and Food Chemistry, 58 (5), 2696-2702.
30. Sparks T.C., Storer N., Porter A., Slater R., Nauen R., 2021. Insecticide resistance management and industry: the origins and evolution of the I nsecticide R esistance A ction C ommittee (IRAC) and the mode of action classification scheme. Pest Management Science, 77 (6), 2609-2619.
31. Suzuki J., Ishida T., Kikuchi Y., Ito Y., Morikawa C., Tsukidate Y., Tanji I., Ota Y., TodaK., 2002. Synthesis and activity of novel acaricidal/ınsecticidal 2, 4-Diphenyl-1, 3-oxazolines. Journal of Pesticide Science, 27 (1), 1-8.
32. Suzuki J., Ishida T., Shibuya, I., Toda K., 2001. Development of a new acaricide, etoxazole. Journal of Pesticide Science, 26 (2), 215-223.
33. Tian Q., Du T., Xu A., Li Y., 2024. Design, synthesis, and 3D-QASR of oxazoline derivatives containing an S–S moiety as potential acaricide. Journal of Agricultural and Food Chemistry, 72 (43), 23727-23735.
34. Van Leeuwen T., Tirry L., Yamamoto A., Nauen R., Dermauw W., 2015. The economic importance of acaricides in the control of phytophagous mites and an update on recent acaricide mode of action research. Pesticide Biochemistry and Physiology, 121, 12-21.
35. Van Leeuwen T., Van Pottelberge S., Tirry,L., 2006. Biochemical analysis of a chlorfenapyr‐selected resistant strain of Tetranychus urticae Koch. Pest Management Science: Formerly Pesticide Science, 62 (5), 425-433.
36. Vitaku E., Smith D.T., Njardarson J.T., 2014. Analysis of the structural diversity, substitution patterns, and frequency of nitrogen heterocycles among US FDA approved pharmaceuticals: miniperspective. Journal of Medicinal Chemistry, 57 (24), 10257-10274.
37. Wagener M., Lommerse J.P., 2006. The quest for bioisosteric replacements. Journal of Chemical Information and Modeling, 46 (2), 677-685.
38. Wu M., Zhang Y., Tian T., Xu D., Wu Q., Xie W., ZhangY., Crickmore N., Guo Z., Wang S. 2023. Assessment of the role of an ABCC transporter TuMRP1 in the toxicity of abamectin to Tetranychus urticae. Pesticide Biochemistry and Physiology, 195 105543.
39. Yu X., Liu Y., Li Y., Wang Q., 2015. Design, synthesis, and acaricidal/insecticidal activities of oxazoline derivatives containing a sulfur ether moiety. Journal of Agricultural and Food Chemistry, 63 (44), 9690-9695.
40. Zhang W., 2017. Mesoionic pyrido [1, 2-a] pyrimidinone insecticides: from discovery to triflumezopyrim and dicloromezotiaz. Accounts of Chemical Research, 50 (9), 2381-2388.
41. Zhang Y., Chen Y., Xun X., Chen S., Liu Y., Wang Q., 2022. Design, synthesis, acaricidal activities, and structure–activity relationship studies of oxazolines containing ether moieties. Journal of Agricultural and Food Chemistry, 70 (42), 13538-13544.
42. Zhang S., Luo Y., He L.Q., Liu Z.J., Jiang A.Q., Yang Y.H., Zhu H.L., 2013. Synthesis, biological evaluation, and molecular docking studies of novel 1, 3, 4-oxadiazole derivatives possessing benzotriazole moiety as FAK inhibitors with anticancer activity. Bioorganic & Medicinal Chemistry, 21 (13), 3723-3729.
43. Ziyaev A.A., Ismailova D.S., 2017. Biological activity of 5-(2, 3, 4-Pyridyl)-1, 3, 4-oxadiazol-2-thiones and their derivatives. World Journal of Pharmaceutical Research, 6 (4), 52-77.
44. Zu G., Gan X., Xie D., Yang H., Zhang A., Li S., Hu D., Song B., 2020. Design, synthesis, and anti-ToCV activity of novel 4 (3 H)-quinazolinone derivatives bearing dithioacetal moiety. Journal of Agricultural and Food Chemistry, 68 (20), 5539-5544.