Hexaconazole

Hexaconazole
Names
	Systematic IUPAC name 2-(2,4-Dichlorophenyl)-1-(1H-1,2,4-triazol-1-yl)hexan-2-ol
Identifiers
CAS Number	79983-71-4 ;
3D model (JSmol)	Interactive image; Interactive image;
Beilstein Reference	8328399
ChemSpider	59833 ; 21173802 (S) ;
ECHA InfoCard	100.101.232
EC Number	413-050-7;
KEGG	C18466 ;
MeSH	Hexaconazole
PubChem CID	66461; 37888330 (R); 37888329 (S);
RTECS number	XZ4803200;
UN number	3077
CompTox Dashboard (EPA)	DTXSID4034653 ;
	InChI InChI=1S/C14H17Cl2N3O/c1-2-3-6-14(20,8-19-10-17-9-18-19)12-5-4-11(15)7-13(12)16/h4-5,7,9-10,20H,2-3,6,8H2,1H3 Key: STMIIPIFODONDC-UHFFFAOYSA-N ;
	SMILES CCCCC(O)(Cn1cncn1)c1ccc(Cl)cc1Cl; CCCCC(O)(CN1C=NC=N1)C1=CC=C(Cl)C=C1Cl;
Properties
Chemical formula	C14H17Cl2N3O
Molar mass	314.21 g·mol−1
Appearance	White crystalline solid
Melting point	111 °C (232 °F; 384 K)
Hazards
	GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H302, H317, H411
Precautionary statements	P273, P280
	Lethal dose or concentration (LD, LC):
LD50 (median dose)	6071 mg/kg (oral, female rat)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Hexaconazole is a systemic fungicide used for the control of many fungi particularly Ascomycetes and Basidiomycetes.

Nomenclature

Common name hexaconazole (BSI, ANSI, draft E-ISO, (m) draft F-ISO) IUPAC name (RS)-2-(2,4-dichlorophenyl)-1-(1H-1,2,4-triazol-1-yl)hexan-2-ol Chemical Abstracts name (?-a-butyl-a-(2,4-dichlorophenyl)-1H-1,2,4-triazole-1-ethanol) CAS RN [79983-71-4] Development codes PP523; ICIA0523 (both ICI)

Chemistry

Composition Tech. is >85% pure. Mol. wt. 314.2 M.f. C14H17Cl2N3O Form White, crystalline solid. M.p. 110-112 °C V.p. 0.018 mPa (20 °C) KOW logP = 3.9 (20 °C) Henry 3.33 ´ 10-4 Pa m3 mol-1 (calc.) S.g./density 1.29 g/cm3 (25 °C) Solubility In water 0.017 g/l (20 °C). In dichloromethane 336, methanol 246, acetone 164, ethyl acetate 120, toluene 59, hexane 0.8 (all in g/l, 20 °C). Stability Stable for at least 6 years at ambient temperatures. Stable to hydrolysis and photolysis in water. Formulations stable in sales containers for 6 months at 50 °C, and 2 years at ambient temperature.

Commericalisation

History Fungicide introduced by ICI Agrochemicals (now Syngenta AG) and first marketed in 1986. Manufacturers Rallis; Sannong; Sharda; Syngenta

Applications

Biochemistry Inhibits ergosterol biosynthesis (steroid demethylation inhibitor). Mode of action Systemic fungicide with protective and curative action. Uses Control of many fungi, particularly Ascomycetes and Basidiomycetes, e.g. Podosphaera leucotricha and Venturia inaequalis on apples, Guignardia bidwellii and Uncinula necator on vines, Hemileia vastatrix on coffee, and Cercospora spp. on peanuts, at 15-250 g/ha. Also used on bananas, cucurbits, peppers and other crops. Phytotoxicity Non-phytotoxic when used as directed. Some injury noted on McIntosh apples. Formulation types OL; SC; SG. Selected products: 'Anvil' (fruit) (Syngenta); 'Planete' (cereals) (Syngenta); 'Canvil' (Vapco); 'Contaf' (Rallis); 'Elexa' (Cequisa); 'Force' (Devidayal); mixtures: 'Columbia' (+ fenpropidin) (Syngenta)

Analysis

Product by glc and FID. Residues by glc with either NPD, thermionic or ECD detection. See K. J. Harradine et al., in Comp. Anal. Profiles, Chapt. 2.

Mammalian toxicology

Reviews FAO/WHO 59, 61 (see part 2 of the Bibliography). Oral Acute oral LD50 for male rats 2189, female rats 6071 mg/kg. Skin and eye Acute percutaneous LD50 for rats >2000 mg/kg. Mild irritant to eyes; non-irritating to skin (rabbits). Moderate skin sensitiser (guinea pigs). Inhalation LC50 (4 h) for rats >5.9 mg/l. NOEL NOAEL (2 y) for rats 10 mg/kg diet; NOAEL (2 y) for mice 40 mg/kg diet. ADI (JMPR) 0.005 mg/kg b.w. [1990]. Other Non-mutagenic. Toxicity class WHO (a.i.) U; EPA (formulation) IV EC classification Xn; R22| R43| N; R51, R53

Ecotoxicology

Birds Acute oral LD50 for mallard ducks >4000 mg/kg. Fish LC50 (96 h) for rainbow trout 3.4, mirror carp 5.94, sheepshead minnow 5.4 mg/l. Daphnia LC50 (48 h) 2.9 mg/l. Bees Acute oral and contact LD50 for honeybees >0.1 mg/bee. Worms LC50 (14 d) 414 mg/kg.

Enviromental fate

Animals Readily excreted by mammals, with no significant retention in organs or tissues. Plants For details of the metabolism of hexaconazole in cereals, see M. W. Skidmore et al., Br. Crop Prot. Conf. - Pests Dis., 1990, 3, 1035-1040. Soil/Environment Rapidly degraded in soils in laboratory tests.

References

^ ^a ^b Hexaconazole, Crop Protection Dictionary, Farm Chemicals International

External links

Hexaconazole chemdata

[CPD-1] Hexaconazole, Crop Protection Dictionary, Farm Chemicals International

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