Nomenclature

Type Insecticide
Common name Amitraz
Other name
Iupac name

N-methylbis(2,4-xylyliminomethyl)amine

Formulation type
Formulation TypeOptions
98%TC  
20%EC  
Chemical Abstracts Name

N'-(2,4-dimethylphenyl)-N-[[(2,4-dimethylphenyl)imino]methyl]-N-methylmethanimidamide

CAS RN [33089-61-1]
EEC no 251-375-4
Official code OMS 1820; ENT 27 967
Development code BTS 27 419 (Boots)

Physical Chemistry

M.F.

C19H23N3

Structure M
Mol. wt 293.4
Appearance

White/pale yellow crystalline solid. 

M.p.

86-88 ºC 

B.p.
V.p.

V.p. 0.34 mPa (25 ºC) using clapeyron-clausius analysis 

F.p.
S.g./density

 1.128 (20 ºC) 

Solubility

 In water <0 .1 mg/l (20 ºC). Soluble in most organic solvents; in acetone, toluene, xylene >300 g/l. 

Stability

Hydrolysis DT50 (25 ºC) 2.1 h (pH 5), 22.1 h (pH 7), 25.5 h (pH 9). U.V. light appears to have little effect on stability. 

Henry
KowlogP

5.5 (25 ℃, pH 5.8

Pka

4.2, weak base 

Applications

Biochemistry

Mode of action probably involves an interaction with octopamine receptors in the tick nervous system, causing an increase in nervous activity. 

Mode of Action

Non-systemic, with contact and respiratory action. Expellent action causes ticks to withdraw mouthparts rapidly and fall off the host animal. 

Uses

Control of all stages of tetranychid and eriophyid mites, pear suckers, scale insects, mealybugs, whitefly, aphids, and eggs and first instar larvae of Lepidoptera on pome fruit, citrus fruit, cotton, stone fruit, bush fruit, strawberries, hops, cucurbits, aubergines, capsicums, tomatoes, ornamentals, and some other crops. Also used as an animal ectoparasiticide to control ticks, mites and lice on cattle, dogs, goats, pigs and sheep.

Phytotoxicity

At high temperatures, young capsicums and pears may be injured. 

Compatibility

Incompatible with alkaline materials, parathion, and others.

General details

Mammalian Toxicology

Reviews

FAO/WHO 83, 85 (see part 2 of the Bibliography). 

Oral

Acute oral LD50 for rats 650, mice >1600 mg/kg. 

Skin & Eye

Acute percutaneous LD50 for rabbits >200, rats >1600 mg/kg. 

Inhalation

LC50 (6 h) for rats 65 mg/l air. 

Noel

In 2 y feeding trials, no adverse effect observed in rats receiving 50-200 ppm diet, or in dogs dosed 0.25 mg/kg daily. Human NOEL >0.125 mg/kg daily. 

ADI

(JMPR) 0.01 mg/kg b.w. [1998]. 

Toxicity class

WHO (a.i.) III; EPA (formulation) III

EC hazard

Xn; R22 

Ecotoxicology

Birds

LD50 for bobwhite quail 788 mg/kg. LC50 (8 d) for mallard ducks 7000, Japanese quail 1800 mg/kg. 

Fish

LC50 (96 h) for rainbow trout 0.74, bluegill sunfish 0.45 mg/l. Due to rapid hydrolysis, it is unlikely that this toxicity will be expressed in natural aquatic systems.  

Daphnia

LC50 (48 h) 0.035 mg/l. Due to rapid hydrolysis, it is unlikely that this toxicity will be expressed in natural aquatic systems. 

Algae

EC50 for Selenastrum capricornutum >12 mg/l.

Worms

LC50 (14 d) for earthworms >1000 mg tech./kg. 

Environmental Fate

Plants

Rapidly degraded, mainly to N-(2,4-dimethylphenyl)-N'-methylformamidine and, to a smaller extent, to 2,4-dimethylformanilide. 

Animals

Rapid breakdown leading to excretion as a conjugate of 4-amino-3-methylbenzoic acid and, to a lesser extent, to N-(2,4-dimethylphenyl)-N'-methylformamidine. 

Soil/environment

Rapidly broken down in soil under aerobic conditions (J. Appl. Bacteriol., 1977, 42, 187; ibid. 1978, 44, 383); DT50 in soil <1 d. Degradation occurs more rapidly in acid than in neutral or alkaline soils. Very strongly adsorbed to soil; Koc c. 1000-2000

Miscellaneous

Analysis

Product analysis by glc (CIPAC Handbook, 1995, G, 5-10).

Packing