N-methylbis(2,4-xylyliminomethyl)amine

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

C₁₉H₂₃N₃

White/pale yellow crystalline solid. 

86-88 ºC 

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

 1.128 (20 ºC) 

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

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. 

5.5 (25 ℃, pH 5.8

4.2, weak base 

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

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

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.

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

Incompatible with alkaline materials, parathion, and others.

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

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

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

LC50 (6 h) for rats 65 mg/l air. 

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. 

(JMPR) 0.01 mg/kg b.w. [1998]. 

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

Xn; R22 

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

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.  

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

EC50 for Selenastrum capricornutum >12 mg/l.

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

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

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. 

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

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