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Benzoylurea insecticide

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Class of insecticide
Chemical structure ofdiflubenzuron, a commonly used benzoylurea insecticide

Benzoylureas (BPUs) are chemicalderivatives ofN-benzoyl-N-phenylurea, which are used asinsecticides.[1] They do not directly kill the insect, but disrupt moulting and egg hatch, and thus act asinsect growth regulators. They act by inhibitingchitin synthase,[2] preventing the formation ofchitin in the insect's body.

The insecticidal activity of the BPUs was discovered serendipitiously at Phillips-Duphar who commericaliseddiflubenzuron in 1975.[1] Since then, many BPUs were commercialised by many companies. BPUs accounted for 3% of the $ 18.4 billion world insecticide market in 2018.[3] Lufenuron, was the largest selling BPU in 2016, selling for $ 112 million.[4]

BPUs are active against many types of insect pests, (e.g. lepidoptera coleoptera, diptera) in agriculture,[1][5] as well as being used against termites and animal health pests such as fleas.[6]

TheInsecticide Resistance Action Committee (IRAC) lists the following BPUs, which are classified in IRAC group 15:[7]bistrifluron,chlorfluazuron,diflubenzuron,flucycloxuron,flufenoxuron,hexaflumuron,lufenuron,novaluron,noviflumuron,teflubenzuron, andtriflumuron. Many older BPUs are no longer in use.[1][5]

Mammalian and environmental toxicity

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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.[8]

BPUs  have low acute toxicity against bees, low to moderate toxicity to fish, but high toxicity to aquatic invertebrates and crustaceans.[1]

BPUs have various rates of degradation in the environment. Some older BPUs have high persistance and are no longer sold.[1]Flufenoxuron was shown tobioaccumulate and was banned in the EU in 2011.[9]

References

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  1. ^abcdefSun, 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)
  2. ^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.
  3. ^Sparks, Thomas C. (14 February 2024)."Insecticide mixtures—uses, benefits and considerations".Pest Management Science.doi:10.1002/ps.7980.PMID 38356314 – via Wiley.
  4. ^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.
  5. ^abPener, 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.
  6. ^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.Open access icon
  7. ^"The IRAC Mode of Action Classification Online".Insecticide Resistance Action Committee. Retrieved5 June 2024.
  8. ^Guidelines for Drinking‑water Quality (4th ed.). Switzerland: World Health Organization. 2017. pp. 435–436.ISBN 978-92-4-154995-0.
  9. ^Commission Implementing Regulation (EU) No 942/2011 of 22 September 2011 concerning the non-approval of the active substance flufenoxuron
Carbamates
Inorganic compounds
Insect growth regulators
Neonicotinoids
Organochlorides
Organophosphorus
Pyrethroids
Diamides
Other chemicals
Metabolites
Biopesticides
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