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Diflubenzuron

From Wikipedia, the free encyclopedia
Diflubenzuron
Names
Preferred IUPAC name
N-[(4-Chlorophenyl)carbamoyl]-2,6-difluorobenzamide
Other names
Dimilin
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.047.740 Edit this at Wikidata
KEGG
UNII
  • InChI=1S/C14H9ClF2N2O2/c15-8-4-6-9(7-5-8)18-14(21)19-13(20)12-10(16)2-1-3-11(12)17/h1-7H,(H2,18,19,20,21) checkY
    Key: QQQYTWIFVNKMRW-UHFFFAOYSA-N checkY
  • Clc2ccc(NC(=O)NC(=O)c1c(F)cccc1F)cc2
Properties[1]
C14H9ClF2N2O2
Molar mass 310.68 g·mol−1
0.08 mg/L
Solubility in other solvents DMSO: 12 g/100 g
Acetone 0.615 g/100 g
Methanol: 0.09 g/100 g
Pharmacology
QP53BC02 (WHO)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkYX markN ?)

Diflubenzuron is an insecticide of the benzoylurea class.[2] It is used in forest management and on field crops[3] to selectively control insect pests, particularly forest tent caterpillar moths, boll weevils, gypsy moths, and other types of moths.[1] It is a widely used larvicide in India for control of mosquito larvae by public health authorities. Diflubenzuron is recommended by the WHO Pesticide Evaluation Scheme for use against mosquitos.[4]

Mechanism of action

[edit]

The mechanism of action of diflubenzuron involves inhibiting the production of chitin which is used by an insect to build its exoskeleton. It triggers insect larvae to molt early without a properly formed exoskeleton, resulting in the death of the larvae.

Mammalian toxicity

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Diflubenzuron has been evaluated by the United States Environmental Protection Agency (EPA), and it is classified as non-carcinogenic. 4-Chloroaniline, a metabolite of diflubenzuron which has been classified as a carcinogen, is produced after diflubenzuron has been ingested. The small amount converted to 4-chloroaniline after ingestion is not sufficient to cause cancer.[5]

Commercial uses

[edit]

Diflubenzuron is used in many products for various purposes.

Dimilin was the first product sold with diflubenzuron as active ingredient. It is still sold as wettable powder (WP-25 ) and various concentrations as suspension concentrate (SC). It is used on a wide variety of crops and target insects.[6]

Micromite (UPL corporation) is sold in two formulations: water dispersible granules (WGS) containing 80% diflubenzuron, and an emulsifiable concentrate (EC) containing 22% diflubenzuron. It is used on a wide variety of crops and target insects.[7]

Adept (OHP, Inc.) is sold as a 25% wettable powder (WP) formulation for ornamental crops in greenhouses. It is used for the control of fungus gnats, shore flies, armyworms, leafminers and suppression of whiteflies.[8][9][10]

Device (Arysta LifeScience) for vector control.[11]

Clarifly (Central Garden & Pet)[12] and JustiFly (Champion).[13] are feed-through cattle treatments to control horn flies and face flies. Vigilante, formulated as a bolus for this purposeis no longer sold.

References

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  1. 1 2 https://extoxnet.orst.edu/pips/difluben.htm Diflubenzuron Pesticide Information Profile], Extension Toxicology Network
  2. ↑ 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
  3. ↑ Johnson, Douglas (2016). "Insecticide Recommendations for Soybeans - 2016" (PDF). Cooperative Extension Service. University of Kentucky: College of Agriculture, Food and Environment. Archived from the original (PDF) on 9 March 2016. Retrieved 16 February 2016.
  4. ↑ Zaim, M. (6 March 2006). "Report of the ninth WHOPES working group meeting, WHO/HQ, Geneva, 5–9 December 2005". World Health Organisation. Retrieved 11 September 2026.
  5. ↑ "Reregistration Eligibility Decision Diflubenzuron" (PDF). Environmental Protection Agency. Retrieved 16 November 2016.
  6. ↑ "RESTRICTED USE PESTICIDE: Dimilin 2L" (PDF). UNITED STATES ENVIRONMENTAL PROTECTION AGENCY. Retrieved 22 September 2027. {{cite web}}: Check date values in: |access-date= (help)
  7. ↑ "Micromite 2L Insecticide" (PDF). UPL corporation. Retrieved 22 September 2026.
  8. ↑ "Adept® Insect Growth Regulator". OHP, Inc. Retrieved 22 September 2026.
  9. ↑ "ADEPT Insect Growth Regulator" (PDF).
  10. ↑ "Adept label" (PDF).
  11. ↑ "Device 25WP". World Health Organisation. Retrieved 22 September 2026.
  12. ↑ "Feed-Through Fly Control". Central Garden & Pet Company. Retrieved 22 September 2026.
  13. ↑ "JustiFly 0.67% Diflubenzuron Larvicide Premix". drugs.com. Retrieved 22 September 2026.
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