Cyromazine

Cyromazine

NOMENCLATURE
Common name cyromazine (BSI, draft E-ISO, (f) draft F-ISO, ANSI)
IUPAC name N-cyclopropyl-1,3,5-triazine-2,4,6-triamine
Chemical Abstracts name N-cyclopropyl-1,3,5-triazine-2,4,6-triamine
CAS RN [66215-27-8] Development codes CGA 72 662 (Ciba-Geigy) Official codes OMS 2014

PHYSICAL CHEMISTRY
Mol. wt. 166.2 M.f. C6H10N6 Form Colourless crystals. M.p. 224.9 °C V.p. 4.48 ´ 10-4 mPa (25 ºC) (OECD 104) KOW logP = -0.061 (pH 7.0) (OECD 107) Henry 5.8 ´ 10-9 Pa m3 mol-1 (calc.) S.g./density 1.35 (20 ºC) Solubility In water 13 g/l (OECD 105) (pH 7.1, 25 ºC). In methanol 22, isopropanol 2.5, acetone 1.7, n-octanol 1.2, dichloromethane 0.25, toluene 0.015, hexane 0.0002 (all in g/kg, 20 ºC). Stability Stable up to 310 ºC. Stable to hydrolysis for 28 days at up to 70 ºC. pKa 5.22, weak base

COMMERCIALISATION
History Insect growth regulator reported by R. D. Hall et al. (J. Econ. Entomol., 1980, 73, 564) and by R. E. Williams et al. (Poultry Sci., 1980, 59, 2207). Introduced as an insecticide by Ciba-Geigy AG (now Syngenta AG). Patents GB 1587573; BE 857896 Manufacturers Gilmore; Sannong; Syngenta

APPLICATIONS
Biochemistry Chitin synthesis inhibitor. Mode of action Insect growth regulator with contact action, which interferes with moulting and pupation. When used on plants, action is systemic: applied to the leaves, it exhibits a strong translaminar effect; applied to the soil, it is taken up by the roots and translocated acropetally. Uses Control of Diptera larvae in chicken manure by feeding to the poultry or treating the breeding sites. Also used to control flies on animals. Used as a foliar spray to control leaf miners (Liriomyza spp.) in vegetables (e.g. celery, melons, tomatoes, lettuce), mushrooms, potatoes and ornamentals, at 75-225 g/ha; also used at 190-450 g/ha in drench or drip irrigation