Benzoylurea Explained

Benzoylureas (BPUs) are chemical derivatives of N-benzoyl--phenylurea, which are used as insecticides.[1] 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,[2] 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.[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,[5] as well as being used against termites and animal health pests such as fleas.[6]

The Insecticide Resistance Action Committee (IRAC) lists the following PBUs, which are classified in IRAC group 15.[7] Bistrifluron, Chlorfluazuron, Diflubenzuron, Flucycloxuron, Flufenoxuron, Hexaflumuron, Lufenuron, Novaluron, Noviflumuron, Teflubenzuron, Triflumuron. Many older BPUs are no longer in use.

3-(Iodoacetamido)-benzoylurea (3-IAABU) is one of several benzoylurea compounds which have been investigated as potential anticancer agents.[8]

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.[9]

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.[10]

Further reading

Notes and References

  1. Sun . Ranfeng . Liu . Chunjuan . Hao . Zhang . Wang . Qingmin . July 13, 2015 . 2015 . Benzoylurea Chitin Synthesis Inhibitors . J. Agric. Food Chem. . 63 . 31 . 6847–6865. 10.1021/acs.jafc.5b02460 . 26168369 .
  2. Douris . Vassilis . Steinbach . Denise . Panteleri . Rafaela . Livadaras . Ioannis . Pickett . John Anthony . Van Leeuwen . Thomas . Nauen . Ralf . Vontas . John . 2016 . Proceedings of the National Academy of Sciences . 2016 . 113 . 51 . 14692–14697. 10.1073/pnas.1618258113 . free . 27930336 . 5187681 .
  3. Sparks . Thomas C. . 14 February 2024 . Insecticide mixtures—uses, benefits and considerations . Pest Management Science . 10.1002/ps.7980 . 38356314 . Wiley.
  4. Book: Jeschke . Peter . Modern Crop Protection Compounds . Witschel . Matthias . Krämer . Wolfgang . Schirmer . Ulrich . Wiley . 2019 . 9783527699261 . 3rd . 25 January 2019 . 1067–1102 . English . Chapter 30: Chitin Biosynthesis.
  5. Pener . Meir Paul . Dhadialla . Tarlochan S. . 2012 . An Overview of Insect Growth Disruptors; Applied Aspects . Advances in Insect Physiology . 43 . 1–162 . 10.1016/B978-0-12-391500-9.00001-2 . 9780123915009 . 0065-2806 . 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 . 10.1051/parasite/2019026 . 1776-1042 . 6492539 . 31041897.
  7. Web site: The IRAC Mode of Action Classification Online . 5 June 2024 . Insecticide Resistance Action Committee.
  8. 3-(Iodoacetamido)-benzoylurea: a novel cancericidal tubulin ligand that inhibits microtubule polymerization, phosphorylates bcl-2, and induces apoptosis in tumor cells . Cancer Research. 58. 23. Jiang . J. D. . Davis . A. S. . 1998-12-01 . 5389–5395 . 9850070 . Middleton . K. . Ling . Y. H. . Perez-Soler . R. . Holland . J. F. . Bekesi . J. G..
  9. Book: Guidelines for Drinking‑water Quality . World Health Organization . 2017 . 978-92-4-154995-0 . 4th . Switzerland . 435–436.
  10. http://eur-lex.europa.eu/LexUriServ/LexUriServ.do?uri=OJ:L:2011:246:0013:0015:EN:PDF Commission Implementing Regulation (EU) No 942/2011 of 22 September 2011 concerning the non-approval of the active substance flufenoxuron

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