Flufenoxuron

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Flufenoxuron
Names
Preferred IUPAC name
N-({4-[2-Chloro-4-(trifluoromethyl)phenoxy]-2-fluorophenyl}carbamoyl)-2,6-difluorobenzamide
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard Lua error in Module:Wikidata at line 880: attempt to index field 'wikibase' (a nil value). Lua error in Module:Wikidata at line 880: attempt to index field 'wikibase' (a nil value).Lua error in Module:EditAtWikidata at line 29: attempt to index field 'wikibase' (a nil value).
EC Number
  • 417-680-3
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KEGG
UNII
  • {{#property:P3117}}Lua error in Module:EditAtWikidata at line 29: attempt to index field 'wikibase' (a nil value).
  • InChI=1S/C21H11ClF6N2O3/c22-12-8-10(21(26,27)28)4-7-17(12)33-11-5-6-16(15(25)9-11)29-20(32)30-19(31)18-13(23)2-1-3-14(18)24/h1-9H,(H2,29,30,31,32)
    Key: RYLHNOVXKPXDIP-UHFFFAOYSA-N
  • C1=CC(=C(C(=C1)F)C(=O)NC(=O)NC2=C(C=C(C=C2)OC3=C(C=C(C=C3)C(F)(F)F)Cl)F)F
Properties
C21H11ClF6N2O3
Molar mass 488.77 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Flufenoxuron is an insecticide that belongs to the benzoylurea chitin synthesis inhibitor group, which also includes diflubenzuron, triflumuron, and lufenuron.[1][2]

Application

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caterpillar of agrotis ipsilon

Flufenoxuron is used as an insecticide primarily on citrus plants, cotton, grape, tea and soybean.[3]

Due to the development of resistance in some cases, the effects of chlorfluazuron and flufenoxuron on selected developmental and reproductive parameters of the agrotis ipsilon were examined in a study. It was found that chlorfluazuron and flufenoxuron can accelerate vitellogenesis (yolk formation during oocyte development) in the ypsilon owl.[4]

Synthesis

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The multi-step synthesis of flufenoxuron is described in the following reaction sequence:[3]

synthesis of flufenoxuron
synthesis of flufenoxuron

Trade name

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A plant protection product containing the active ingredient flufenoxuron is marketed under the trade name Cascade[3].

Authorization

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No plant protection products containing this active ingredient are authorized in Germany or in the EU.[2]

Properties

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Flufenoxuron is a white crystalline powder. It has low solubility in water, is not flammable, and is not an oxidizer.[1]

Toxicology and safety

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Flufenoxuron toxicity to humans and other mammals is low,[1] but it has a potentially high bioaccumulation in fish despite its low water solubility.[5]

References

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  1. ^ a b c Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).
  2. ^ a b Entry on Flufenoxuron. at: Römpp Online. Georg Thieme Verlag, retrieved {{{Datum}}}.
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