benzoylurea derivatives, a novel class of herbizides [1]

[1] Ciba-Geigy Res. Discl. 351, 442-7; Chem Abstr. 119 : 271113.


Chitin Synthesis Inhibitors [2] , [3]

Some insect growth regulators inhibit the formation of the chitinous insect exoskeleton and thus produce a critical biochemical lesion at the time of molting, pupation, or ecdysis.
Diflubenzuron [35367-38-5], N-{[(4-chlorophenyl)amino]carbonyl}-2,6-difluorobenzamide, mp 239 °C, is soluble in water to 0.3 mg/L and has an LD50 (rat, oral) of > 4 640 mg/kg. Diflubenzuron is the best known compound with the same general structure that inhibits the synthesis of chitin and is thus very specific for the control of arthropods. Diflubenzuron is an ovicide and a slow-acting broad-spectrum insecticide.


[2] L. C. Post, B. J. deJong, W. R. Vincent, Pestic. Biochem. Physiol. 4 (1974) 473.C. A. Hendrick in J. L. Coats (ed.): Insecticide Mode of Action, Academic Press, New York 1982, p. 315.


Flufenoxuron [101463-69-8], 1-[-4-(2-chloro-a,a,a-trifluoro-p-tolyloxy)-2-fluorophenyl]-3-(2,6-difluorobenzoyl)urea, C21H11ClF6N2O3, Mr 488.8, mp 169 – 172 °C, is a colorless crystalline solid which is practically insoluble in water and moderately soluble in acetone, xylene, dichloromethane [20, p. 568].


Flufenoxuron is produced by reaction of 2-fluoro-4-hydroxyaniline in potassium hydroxide-containing dimethyl sulfoxide with 3,4-dichlorotrifluoromethyltoluene to give the corresponding phenoxyaniline, which is treated with 2,6-difluorophenyl isocyanate [88].
Flufenoxuron is a chitin synthesis inhibitor and insect and acarid growth regulator with contact and stomach action. It is used for control of immature stages of many phytophagous mites and insect pests on pome fruits, vines, citrus fruits, tea, cotton, maize, vegetables, ornamentals, etc.
Trade Name. Cascade (Cyanamid).

[20, p. 568] C. D. S. Tomlin: The Pesticide Manual, 11th ed., British Crop Protection Council, 1997.


Flufenoxuron [101463-69-8]

LD50 (rat, oral) > 3000 mg/kg [20, p. 568]
LD50 (rat, dermal) > 2000 mg/kg [20, p. 568]
LD50 (mouse, dermal) > 2000 mg/kg [20, p. 568]
LC50 (rat, 4-h inhalation) 5 mg/L air [20, p. 568]
Rabbit: nonirritating to skin and eyes [20, p. 568]
NOEL/NOAEL:

Subchronic.



Rat (90-day feed): ca. 3.3 mg kg*–1 d*–1 [20, p. 568]
Mouse (90-day feed):ca. 7.1 mg kg*–1 d*–1 [20, p. 568]
Dog (one-year feed): ca. 2.5 mg kg–1 d–1 [20, p. 568]


[20, p. 568] C. D. S. Tomlin: The Pesticide Manual, 11th ed., British Crop Protection Council, 1997.


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