Hexaflumuron

Description

Hexaflumuron is a benzoylphenyl urea-type insecticide and is the common name for N-(((3,5- dichloro-4-(1,1,2,2-tetrafluoro-ethoxy)phenyl)amino)carbonyl)-2,6-difluorobenzamide. It the active ingredient in several termite control products registered to Dow AgroSciences LLC, a wholly owned subsidiary of The Dow Chemical Company. Hexaflumuron was the first active ingredient to be registered with the U.S. Environmental Protection Agency (EPA) as a reduced-risk pesticide. A reduced-risk pesticide is one that the EPA believes has low impact on human health, low toxicity to non-target organisms, and low potential for groundwater contamination. Hexaflumuron’s mode of action is to inhibit chitin synthesis. Termites produce chitin to form or maintain an exoskeleton.
Hexaflumuron is an odorless white solid that is formulated into low-concentration solid briquettes that are contained within tamper-resistant bait stations. Formulated hexaflumuron briquettes contain about 0.5% of the active ingredient, with the balance comprised almost entirely of cellulose.
Hexaflumuron formulations have been marketed under the trade names RECRUIT® AG termite bait, SHATTER*termite bait, SENTRI*TECH, RECRUTE® Pro, Hex-Pro(TM) Termite Baiting System, Sentricon(TM) IG Termite Bait, Sentricon(TM) AG Termite Bait, Sentricon® Termite Colony Elimination System.

Chemical properties

White solid or powder. The commercial product may be an emulsifiable concentrate.

The Uses of Hexaflumuron

Hexaflumuron is an benzoylphenylurea based chitin synthesis inhibitor used against Ephestia figulilella.

The Uses of Hexaflumuron

Hexaflumuron is used for the control of larvae of Lepidoptera, Coleoptera, Homoptera and Diptera on top fruit, cotton and vegetables. It is also used in forestry.

What are the applications of Application

Hexaflumuron is an insect growth regulator (IGR) that works by interfering with chitin synthesis

Definition

ChEBI: An N-acylurea that is urea in which a hydrogen attached to one of the nitrogens is replaced by a 2,6-difluorobenzoyl group, while a hycrogen attached to the other nitorgen is replaced by a 3,5-dichloro-4-(1,1,2,2-tetrafluoroethoxy)phenyl group.

Potential Exposure

Hexaflumuron is a benzoyl urea insecti cide, termiticide and insect growth regulator (IGR) that inhi bits an insect’s growth through chitin synthesis, which termites need to form an exoskeleton. It is used to impregnate termite bait. Worldwide, there are more than 20 suppliers/ manufacturers; most are in the United States Not currently registered for agricultural use in some EU countries.

Metabolic pathway

Although there is limited dormation on the metabolism of hexaflumuron in the open literature, there is a useful summary provided by Dow Agrosciences (Anon). Metabolic pathways are shown in Scheme 1.

Shipping

UN3077 Environmentally hazardous substances, solid, n.o.s., Hazard class: 9; Labels: 9-Miscellaneous haz ardous material, Technical Name Required.

Degradation

Hexaflumuron is stable to hydrolysis at pH 5.0 (25°C) over 33 days and hydrolysis at pH 7.0 is slow (6% in 33 days). However, hydrolysis at pH 9.0 was more rapid (DT₅₀ 21-23 days). Alkaline hydrolysis followed two separate routes, namely the formation of 2,6-difluorobenzoic acid (2) and 3,5-dichloro-4-( 1,1,2,2-tetrafluoroethoxy)phenylurea (3) and a slower reaction to form 2,6-difluorobenzamide (4) and 3,5-dichloro-4-( 1,1,2,2- tetrafluoroethoxy)anilhe (5).
When [¹⁴C-aniline] and [¹⁴C-benzoyl]hexaflumuron were irradiated in sterile aqueous buffer at pH 5, the DT₅₀ was approximately 6.3 days. The major photolysis product from the benzoyl label was 4 (96% of the applied radioactivity) and from the aniline label was 3,5-dichloro-4- hydroxyaniline (6). The latter comprised 35% of the applied radioactivity and a further 60% was released as ¹⁴CO₂ from the aniline label indicating extensive ring-opening.

Incompatibilities

Decomposes in temperatures above 275 C. Irritating or toxic fumes or gases in a fire

Waste Disposal

Do not discharge into drains or sewers. Dispose of waste material as hazardous waste using a licensed disposal contractor to an approved land fill. Consult with environmental regulatory agencies for guidance on acceptable disposal practices. Incineration with effluent gas scrubbing is recommended. Containers must be disposed of properly by following package label directions or by contacting your local or federal environmental control agency, or by contacting your regional EPA office.