Hexaflumuron Chemical Properties

Melting point:

197-199°

Density 

1.4069 (estimate)

vapor pressure 

5.9 x l0^-5 Pa (25 °C)

storage temp. 

Sealed in dry,2-8°C

solubility 

DMF: 10 mg/ml,DMSO: 10 mg/ml,DMSO:PBS(pH 7.2) (1:2): 0.3 mg/ml

form 

Solid

Water Solubility 

2.7 x l0^-22 mg l^-1 (18 °C)

pka

8.54±0.46(Predicted)

color 

Off-white to light yellow

BRN 

8168725

Stability:

Stable. Incompatible with strong oxidizing agents.

InChIKey

RGNPBRKPHBKNKX-UHFFFAOYSA-N

CAS DataBase Reference

86479-06-3(CAS DataBase Reference)

EPA Substance Registry System

Hexaflumuron (86479-06-3)

Safety Information

Hazard Codes 

N

Risk Statements 

50/53

Safety Statements 

60-61

RIDADR 

UN 3077

WGK Germany 

2

RTECS 

CV3800000

HazardClass 

9

PackingGroup 

III

Hazardous Substances Data

86479-06-3(Hazardous Substances Data)

Toxicity

LD50 oral in rat: > 5gm/kg

Hexaflumuron Usage And Synthesis

Description

Hexaflumuron is a termite pesticide, the first “reduced-risk pesticide” registered by the US EPA. Unlike traditional methods, it is regurgitated at the nest – allowing it to be applied in environmentally-friendly baiting stations, rather than liquid chemical barriers. It is an Insect Growth Regulator (IGR), acting on the synthesis of chitin, the main component of the exoskeleton. Its clearance and metabolism is slow, allowing for a high degree of bioconcentration. It can be used against subterranean termite colonies for wood structures including buildings, fences, trees, decking, and more, to control Reticulitermes, Coptotermes, and Heterotemes.

mechanism of action

Hexaflumuron is an insect growth regulator (IGR) that works by inhibiting the insect’s growth. It interferes with chitin synthesis, which termites need to form a new exoskeleton.
Hexaflumuron is part of a pest monitoring system and is used selectively only in baiting stations where termite activity is present and only when the activity continues. Termites are social insects that share food and feeding sites. Foraging termites recruit nestmates to feeding sites by leaving a pheromone trail to the site, allowing the entire nest to feed on the bait containing hexaflumuron.
Pest control operators use hexaflumuron as part of aboveground and underground baiting systems. They place it in a tamper-resistant bait station where foraging termites consume it.

uses

Hexaflumuron is used to control subterranean termite colonies. It is used in above-ground and inground bait stations as part of termite monitoring and control programs. Target sites include buildings, fences, utility poles, decking, landscape plantings, trees, and other wood structures that can be damaged by termite foraging and feeding. Hexaflumuron products are used only by licensed pest management professionals.
Hexaflumuron is registered by the U.S. Environmental Protection Agency (EPA) for use as termite bait. End-use termite bait formulations containing hexaflumuron are registered and sold in more than 25 countries including Australia, Brazil, China, France, Japan, Spain, and the United States. Formulations are packaged into bait stations for in-ground installation around structures and in stations for above-ground installation.

toxicity

Animals
Hexaflumuron has a low toxicity when fed to rats in laboratory studies. See boxes on LD50,Laboratory Testing box and Toxicity Categories.
Laboratory tests indicate hexaflumuron is nonirritating to the skin and eyes of rabbits.
Humans
Scientists do not consider hexaflumuron a skin sensitizer.

reference

http://msdssearch.dow.com/PublishedLiteratureDOWCOM/dh_091b/0901b8038091b652.pdf?filepath=productsafety/pdfs/noreg/233-00932.pdf&fromPage=GetDoc
http://npic.orst.edu/factsheets/hexgen.pdf
http://www.doityourselftermitecontrol.com/chemical-termite-treatments.html
https://www.caymanchem.com/product/18598
http://dissemination.echa.europa.eu/Biocides/ActiveSubstances/1314-18/1314-18_Assessment_Report.pdf
https://npic.orst.edu/factsheets/archive/hextech.pdf
https://www.epestcontrol.com/images/Products/labels/hexaflumeroninfosheet.pdf

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.

Uses

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

Uses

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.

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.

Hexaflumuron(86479-06-3)Related Product Information

• Pyrethrins
• Dimefluthrin
• Glycine
• Phenylhydrazine
• ALTRENOGEST
• PHENYL VALERATE
• PYRAZOPHOS
• 4-(1,1,2,2-TETRAFLUOROETHOXY)ANILINE
• 3,5-Dichloro-4-(1,1,2,2-tetrafluoroethoxy)aniline
• 4-Amino-2,6-dichlorophenol
• Diflubenzuron W.P.
• Diflubenzuron
• METOXURON-MONOMETHYL
• 3-CHLORO-4-DIFLUOROMETHOXY-PHENYLAMINE
• 1-(3,5-dichlorophenyl)-3-methylurea
• 3-CHLORO-4-ETHOXYANILINE
• (2,6-Difluoro-benzyl)-urea
• Hexaflumuron