Cycloxaprid

Last updated
Cycloxaprid
Cycloxaprid.svg
Names
IUPAC name
(1S,8R)-5-[(6-chloropyridin-3-yl)methyl]-7-nitro-11-oxa-2,5-diazatricyclo[6.2.1.02,6]undec-6-ene
Other names
  • Cycloxaprid
  • (5S,8R)-1-[(6-chloro-3-pyridinyl)methyl]-2,3,5,6,7,8-hexahydro-9-nitro-5,8-Epoxy-1H-imidazo[1,2-a]azepine
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
PubChem CID
  • InChI=1S/C14H15ClN4O3/c15-11-3-1-9(7-16-11)8-17-5-6-18-12-4-2-10(22-12)13(14(17)18)19(20)21/h1,3,7,10,12H,2,4-6,8H2/t10-,12+/m1/s1
    Key: NDHXMRFNYMNBKO-PWSUYJOCSA-N
  • C1C[C@H]2N3CCN(C3=C([C@@H]1O2)[N+](=O)[O-])CC4=CN=C(C=C4)Cl
Properties
C14H15ClN4O3
Molar mass 322.75 g·mol−1
Hazards
GHS labelling:
GHS-pictogram-exclam.svg GHS-pictogram-silhouette.svg GHS-pictogram-pollu.svg
Warning
H302, H312, H315, H319, H332, H351, H410
P273, P280, P301+P312, P305+P351+P338, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Cycloxaprid is a neonicotinoid insecticide derived from the (nitromethylene)imidazole (NMI) analogue of imidacloprid. First reported in 2008., [1] it is a novel insecticide developed to control pests that have developed resistance to imidacloprid, particularly targeting lepidopteran pests and whiteflies in rice cultivation. Currently, limited information is available regarding its environmental impact, ecotoxicology, or effects on human health. [2]

Contents

Chemistry

Cycloxaprid is distinguished by its unique chemical structure, featuring a nitro substituent in the cis-configuration, unlike other commercialized neonicotinoids which have the nitro group in the trans-configuration. It has demonstrated significant efficacy against insecticide-resistant pests, particularly showing 50-fold higher activity against imidacloprid-resistant brown planthopper compared to imidacloprid itself. This enhanced effectiveness against resistant pests makes it a promising alternative in pest management strategies, especially in contexts where repeated imidacloprid applications have led to resistance development. [3]

Neonicotinoids represent the most commonly used class of insecticides globally, valued for their effectiveness against a wide spectrum of insect pests, particularly those in the orders Coleoptera, Diptera, and Lepidoptera. [4] Their applications span both agricultural crop protection and animal health, with common usage methods including plant, soil, and seed treatments. [5] However, ecological concerns have emerged regarding their environmental impact. [6] [7] Studies have documented that imidacloprid, a prominent neonicotinoid, can adversely affect various non-target organisms. [8] These effects include impacts on pollinators and beneficial arthropods, manifesting in behavioral changes, population decline, reduced reproductive success, and increased mortality. Research has also revealed broader ecological consequences, including negative effects on aquatic macroinvertebrates, plankton, crayfish, and mollusks. Furthermore, studies have identified ecosystem-level impacts, such as disruption of songbird migration patterns and decreases in fishery productivity. These findings have motivated the development of alternative insecticides that maintain pest control efficacy while reducing environmental impact.

Mechanism of action

Cycloxaprid’s mode of action was initially believed to be analogous to that of imidacloprid, likely impacting nicotinic acetylcholine receptors [9] [10] [11] However, the exact mode of action is not fully understood. [12] [13] [14]

References

  1. ↑ Shao, Xusheng; Zhang, Wenwen; Peng, Yanqing; Li, Zhong; Tian, Zhongzhen; Qian, Xuhong (2008-12-15). "cis-Nitromethylene neonicotinoids as new nicotinic family: Synthesis, structural diversity, and insecticidal evaluation of hexahydroimidazo[1,2-α]pyridine" . Bioorganic & Medicinal Chemistry Letters. 18 (24): 6513–6516. doi:10.1016/j.bmcl.2008.10.048. ISSN   0960-894X. PMID   18951786.
  2. ↑ Hertfordshire, University of. "Cycloxaprid". sitem.herts.ac.uk. Retrieved 2024-11-09.
  3. ↑ Cui, Li; Qi, Haoliang; Yang, Daibin; Yuan, Huizhu; Rui, Changhui (2016-09-01). "Cycloxaprid: A novel cis-nitromethylene neonicotinoid insecticide to control imidacloprid-resistant cotton aphid (Aphis gossypii)" . Pesticide Biochemistry and Physiology. Insecticide Toxicology in China. 132: 96–101. Bibcode:2016PBioP.132...96C. doi:10.1016/j.pestbp.2016.02.005. ISSN   0048-3575. PMID   27521919.
  4. ↑ Jeschke, Peter; Nauen, Ralf; Schindler, Michael; Elbert, Alfred (2011-04-13). "Overview of the Status and Global Strategy for Neonicotinoids" . Journal of Agricultural and Food Chemistry. 59 (7): 2897–2908. Bibcode:2011JAFC...59.2897J. doi:10.1021/jf101303g. ISSN   0021-8561. PMID   20565065.
  5. ↑ Elbert, Alfred; Haas, Matthias; Springer, Bernd; Thielert, Wolfgang; Nauen, Ralf (November 2008). "Applied aspects of neonicotinoid uses in crop protection" . Pest Management Science. 64 (11): 1099–1105. doi:10.1002/ps.1616. ISSN   1526-498X. PMID   18561166.
  6. ↑ Hladik, Michelle L.; Main, Anson R.; Goulson, Dave (2018-03-20). "Environmental Risks and Challenges Associated with Neonicotinoid Insecticides". Environmental Science & Technology. 52 (6): 3329–3335. Bibcode:2018EnST...52.3329H. doi:10.1021/acs.est.7b06388. ISSN   0013-936X. PMID   29481746.
  7. ↑ Main, Anson R.; Webb, Elisabeth B.; Goyne, Keith W.; Mengel, Doreen (July 2018). "Neonicotinoid insecticides negatively affect performance measures of non-target terrestrial arthropods: a meta-analysis" . Ecological Applications. 28 (5): 1232–1244. Bibcode:2018EcoAp..28.1232M. doi:10.1002/eap.1723. ISSN   1051-0761. PMID   29603486.
  8. ↑ Kobashi, Koji; Harada, Takaaki; Adachi, Yoshihiro; Mori, Miho; Ihara, Makoto; Hayasaka, Daisuke (2017-04-01). "Comparative ecotoxicity of imidacloprid and dinotefuran to aquatic insects in rice mesocosms" . Ecotoxicology and Environmental Safety. 138: 122–129. Bibcode:2017EcoES.138..122K. doi:10.1016/j.ecoenv.2016.12.025. ISSN   0147-6513. PMID   28040617.
  9. ↑ Shao, Xusheng; Swenson, Tami L.; Casida, John E. (2013-08-21). "Cycloxaprid Insecticide: Nicotinic Acetylcholine Receptor Binding Site and Metabolism" . Journal of Agricultural and Food Chemistry. 61 (33): 7883–7888. Bibcode:2013JAFC...61.7883S. doi:10.1021/jf4030695. ISSN   0021-8561. PMID   23889077.
  10. ↑ Ohno, Ikuya; Tomizawa, Motohiro; Durkin, Kathleen A.; Naruse, Yuji; Casida, John E.; Kagabu, Shinzo (2009-03-16). "Molecular Features of Neonicotinoid Pharmacophore Variants Interacting with the Insect Nicotinic Receptor" . Chemical Research in Toxicology. 22 (3): 476–482. doi:10.1021/tx800430e. ISSN   0893-228X. PMID   19178134.
  11. ↑ Talley, Todd T.; Harel, Michal; Hibbs, Ryan E.; Radić, Zoran; Tomizawa, Motohiro; Casida, John E.; Taylor, Palmer (2008-05-27). "Atomic interactions of neonicotinoid agonists with AChBP: Molecular recognition of the distinctive electronegative pharmacophore". Proceedings of the National Academy of Sciences. 105 (21): 7606–7611. Bibcode:2008PNAS..105.7606T. doi: 10.1073/pnas.0802197105 . ISSN   0027-8424. PMC   2396707 . PMID   18477694.
  12. ↑ Cui, Li; Sun, Lina; Yang, Daibin; Yan, Xiaojing; Yuan, Huizhu (November 2012). "Effects of cycloxaprid, a novel cis -nitromethylene neonicotinoid insecticide, on the feeding behaviour of Sitobion avenae" . Pest Management Science. 68 (11): 1484–1491. doi:10.1002/ps.3333. ISSN   1526-498X. PMID   22707457.
  13. ↑ Chang, Xiaoli; Yuan, Yongda; Zhang, Tianshu; Wang, Dongsheng; Du, Xingbin; Wu, Xiangwen; Chen, Haixia; Chen, Yaozhong; Jiao, Yuetong; Teng, Haiyuan (2015). "The Toxicity and Detoxifying Mechanism of Cycloxaprid and Buprofezin in Controlling Sogatella furcifera (Homoptera: Delphacidae)". Journal of Insect Science. 15 (1): 98. doi:10.1093/jisesa/iev077. ISSN   1536-2442. PMC   4677492 . PMID   26175461.
  14. ↑ Zhang, Yixi; Xu, Xiaoyong; Bao, Haibo; Shao, Xusheng; Li, Zhong; Liu, Zewen (January 2019). "The binding properties of cycloxaprid on insect native nAChRs partially explain the low cross-resistance with imidacloprid in Nilaparvata lugens". Pest Management Science. 75 (1): 246–251. doi:10.1002/ps.5108. ISSN   1526-498X. PMID   29877026.
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