Benzoylureas (BPUs) are chemical derivatives of N-benzoyl-N′-phenylurea, which are used as insecticides. They do not directly kill the insect, but disrupt moulting and egg hatch, and thus act as insect growth regulators. They act by inhibiting chitin synthase, preventing the formation of chitin in the insect's body.
The insecticidal activity of the BPUs was discovered serendipitiously at Phillips-Duphar who commericalised diflubenzuron in 1975. Since then, many BPUs were commercialised by many companies. BPUs accounted for 3% of the $ 18.4 billion world insecticide market in 2018. Lufenuron, was the largest selling BPU in 2016, selling for $ 112 million.
BPUs are active against many types of insect pests, (e.g. lepidoptera coleoptera, diptera) in agriculture, as well as being used against termites and animal health pests such as fleas.
The Insecticide Resistance Action Committee (IRAC) lists the following BPUs, which are classified in IRAC group 15: bistrifluron, chlorfluazuron, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, teflubenzuron, and triflumuron. Many older BPUs are no longer in use.
Mammalian and environmental toxicity
BPUs have a good mammalian tox profile. Diflubenzuron is considered to be of very low acute toxicity, and is approved by the WHO for treatment of drinking water as a mosquito larvicide.
BPUs have low acute toxicity against bees, low to moderate toxicity to fish, but high toxicity to aquatic invertebrates and crustaceans.
BPUs have various rates of degradation in the environment. Some older BPUs have high persistance and are no longer sold. Flufenoxuron was shown to bioaccumulate and was banned in the EU in 2011.
References
- ^ Sun, Ranfeng; Liu, Chunjuan; Hao, Zhang; Wang, Qingmin (July 13, 2015). "Benzoylurea Chitin Synthesis Inhibitors". J. Agric. Food Chem. 63 (31): 6847–6865. Bibcode:2015JAFC...63.6847S. doi:10.1021/acs.jafc.5b02460. PMID 26168369.
{{cite journal}}: CS1 maint: date and year (link) - Douris, Vassilis; Steinbach, Denise; Panteleri, Rafaela; Livadaras, Ioannis; Pickett, John Anthony; Van Leeuwen, Thomas; Nauen, Ralf; Vontas, John (2016). "2016". Proceedings of the National Academy of Sciences. 113 (51): 14692–14697. doi:10.1073/pnas.1618258113. PMC 5187681. PMID 27930336.
- Sparks, Thomas C. (14 February 2024). "Insecticide mixtures—uses, benefits and considerations". Pest Management Science. doi:10.1002/ps.7980. PMID 38356314 – via Wiley.
- Jeschke, Peter; Witschel, Matthias; Krämer, Wolfgang; Schirmer, Ulrich (2019). "Chapter 30: Chitin Biosynthesis". Modern Crop Protection Compounds (3rd ed.). Wiley (published 25 January 2019). pp. 1067–1102. ISBN 9783527699261.
- ^ Pener, Meir Paul; Dhadialla, Tarlochan S. (2012). "An Overview of Insect Growth Disruptors; Applied Aspects". Advances in Insect Physiology. 43: 1–162. doi:10.1016/B978-0-12-391500-9.00001-2. ISBN 9780123915009. ISSN 0065-2806 – via Elsevier.
- Junquera, Pablo; Hosking, Barry; Gameiro, Marta; Macdonald, Alicia (2019). "Benzoylphenyl ureas as veterinary antiparasitics. An overview and outlook with emphasis on efficacy, usage and resistance". Parasite. 26: 26. doi:10.1051/parasite/2019026. ISSN 1776-1042. PMC 6492539. PMID 31041897.
- "The IRAC Mode of Action Classification Online". Insecticide Resistance Action Committee. Retrieved 5 June 2024.
- Guidelines for Drinking‑water Quality (4th ed.). Switzerland: World Health Organization. 2017. pp. 435–436. ISBN 978-92-4-154995-0.
- Commission Implementing Regulation (EU) No 942/2011 of 22 September 2011 concerning the non-approval of the active substance flufenoxuron