9093. Tebufenozide

Nomenclature

CAS number: 112410-23-8
3,5-Dimethylbenzoic acid 1-(1,1-dimethylethyl)-2-(4-ethylbenzoyl)hydrazide; N-tert-butyl-N′-(4-ethylbenzoyl)-3,5-dimethylbenzoylhydrazide; RH-5992; Confirm (Dow AgroSci.); Mimic (Dow AgroSci.).
C22H28N2O2; mol wt 352.47.
C 74.97%, H 8.01%, N 7.95%, O 9.08%.

Description and references

Synthetic nonsteroidal ecdysone agonist causing premature molting; novel insect growth regulator specific to lepidopteran species. Prepn: A. C. Hsu, H. E. Aller, AU 64289; eidem, US 4985461 (1986, 1991 both to Rohm & Haas). Properties and field evaluation: J. J. Heller et al., Brighton Crop Prot. Conf. - Pests Dis. 1992, 59. Determn by LC in environmental samples: K. M. S. Sundaram et al., J. AOAC Int. 76, 668 (1993); by GC and LC in formulations: idem, et al., J. Chromatogr. A 687, 323 (1994). Soil adsorption: idem, J. Environ. Sci. Health B29, 415 (1994). Insecticidal activity: G. Smagghe, D. Degheele, Pestic. Sci. 42, 85 (1994). Mechanism of action: A. Retnakaran et al., Insect Biochem. Mol. Biol. 25, 109 (1995). Aquatic toxicology: D. P. Kreutzweiser et al., Ecotoxicol. Environ. Saf. 28, 14 (1994). Review of biological activity and use: H. Oberlander et al., Arch. Insect Biochem. Physiol. 28, 209-223 (1995).

Chemical structure

Properties

mp 191°. Also reported as mp 186-188° (Sundaram, 1081). Vapor pressure (25°): 3 × 108 mm Hg. Also reported as vapor pressure (25°): 1.7 × 106 mm Hg (Sundaram, 415). Soly (25°): 0.83 μg/ml water. Partition coefficient (octanol/water): 32000. LD50 orally in rats, mice: >5000 mg/kg; dermally in rats: >5000 mg/kg; LD50 in honey bees (96 hr, contact): >234 μg/bee; LC50 in mallard duck (8-day dietary): >5000 mg/kg; LC50 in rainbow trout (96 hr): 5.7 mg/l (Heller).

Use

Insecticide.