Description
Fenoxycarb is a non-neurotoxic carbamate insecticide that acts as an insect growth regulator
via juvenile hormone-like activity. It inhibits terminal development of first instar and newly transformed second instar nymphs of Florida red scale (
C. aonidum) when used at a concentration of 0.0125% AI. Fenoxycarb (5 and 10 mg AI/colony) reduces the colony size index of laboratory colonies of red imported fire ants (
S. invicta) by 93.6 to 95.9% at 8 weeks post-treatment. It is toxic to
D. magna (LC
50 = 0.5 mg a.s./L) and fish including
O. mykiss,
L. macrochirus,
C. carpio,
I. punctatus, and
C. variegatus (LC
50s = 0.66-1.5 mg a.s./L), but is not toxic to rats (LD
50 = >10,000 mg/kg). Fenoxycarb is also an antagonist of α4β40-, α4β2-, α3β4-, and α3β2-containing rat nicotinic acetylcholine receptors (nAChRs; IC
50s = 3, 2.4, 1.8, and 7.6 μM, respectively) but not rat brain acetylcholinesterase (AChE; IC
50 = >1,000 μM).
Chemical Properties
Colorless crystalline
Uses
Fenoxycarb is a carbamate insect growth regulator by preventing immature insects from reaching maturity by mimicking juvenile hormone.
Definition
ChEBI: Fenoxycarb is a carbamate ester that is the O-ethyl carbamate of 2-(4-phenoxyphenoxy)ethylamine. It has a role as a juvenile hormone mimic, an environmental contaminant, a xenobiotic and an insecticide. It is an aromatic ether and a carbamate ester. It is functionally related to a 4-phenoxyphenol.
General Description
White crystalline solid. Selective insecticide.
Air & Water Reactions
Slightly water soluble.
Reactivity Profile
Ethyl 2-(4-phenoxyphenoxy)ethylcarbamate is a carbamate ester. Carbamates are chemically similar to, but more reactive than amides. Like amides they form polymers such as polyurethane resins. Carbamates are incompatible with strong acids and bases, and especially incompatible with strong reducing agents such as hydrides. Flammable gaseous hydrogen is produced by the combination of active metals or nitrides with carbamates. Strongly oxidizing acids, peroxides, and hydroperoxides are incompatible with carbamates.
Flammability and Explosibility
Not classified
Agricultural Uses
Insecticide, Miticide: Fenoxycarb is an insect growth regulator, sex attractant,
or feeding stimulant. It is intended to be used to inhibit
metamorphosis of juvenile insects to the adult stage.
It is used as bait to control a broad spectrum of insects on
olives, vines, fruit, cotton, and stored products. It is used to
control fire ants, cockroaches, mosquitos, beetles, moths,
scale and sucking insects.
Trade name
AWARD; ABG 6215; ACR®-2984 F; ACR®
2913; BASUS®[C]; COMPLY®; ECTOGARD®[C];
ELIMINATOR®[C]; INSEGAR®; LogIC®; LUFOX®;
PICTYL®; PRECISION®; TORUS®[C]; RO 13-5223®;
VARIKILL®
Synthesis
N-chloroethyl carbamate was prepared by reacting cycloethylamine with ethyl chloroformate, and then reacted with phenoxyphenol to obtain Ethyl 2-(4-phenoxyphenoxy)ethylcarbamate.
References
[1] SIMON GRENIER ANNE M G. Fenoxycarb, a fairly new Insect Growth Regulato: review of its effects on insects[J]. Annals of Applied Biology, 1993, 122 2: 369-403. DOI:
10.1111/j.1744-7348.1993.tb04042.x[2] PELEG B. Effect of a new insect growth regulator, RO 13-5223, on hymenopterous parasites of scale insects[C]//19 1. 1983: 0. DOI:
10.1007/bf02372190[3] W. A. BANKS C S L David F Williams. Effectiveness of Fenoxycarb for Control of Red Imported Fire Ants (Hymenoptera: Formicidae)[J]. Journal of Economic Entomology, 1988, 81 1: 83-87. DOI:
10.1093/jee/81.1.83[4] AUTHORITY E F S. Conclusion on the peer review of the pesticide risk assessment of the active substance fenoxycarb[C]//8 12. 2010. DOI:
10.2903/j.efsa.2010.1779
