Tebuconazole

TC & FORMULATION: 97%TC, 430G/L SC, 6%FS, 25%EC, 25%EW, 80%WP

Structure Formula  

NOMENCLATURE

Common name tebuconazole (BSI, draft E-ISO)

IUPAC name (RS)-1-p-chlorophenyl-4,4-dimethyl-3-(1H-1,2,4-triazol-1-ylmethyl)pentan-3-ol 

Chemical Abstracts name (?-a-[2-(4-chlorophenyl)ethyl]-a-(1,1-dimethylethyl)-1H-1,2,4-triazole-1-ethanol 

Other names fenetrazole*; terbuconazole*; terbutrazole*; ethyltrianol*  CAS RN [107534-96-3]  EEC no. ELINCS: 403-640-2 

PHYSICAL CHEMISTRY

Composition Racemate.  Mol. wt. 307.8  M.f. C16H22ClN3O  Form Colourless crystals; (tech., colourless to light brown powder).  M.p. 105 ºC  V.p. 1.7 ´ 10-3 mPa (20 ºC) (OECD 104)  KOW logP = 3.7 (20 °C)  Henry 1 ´ 10-5 Pa m3 mol-1 (20 °C)  S.g./density 1.25 (26 °C)  Solubility In water 36 mg/l (pH 5-9, 20 ºC). In dichloromethane >200, isopropanol, toluene 50-100, hexane <0.1 (all in g/l, 20 ºC).  Stability Stable to elevated temperatures, and to photolysis and hydrolysis in pure water, under sterile conditions; hydrolysis DT50 >1 y (pH 4-9, 22 °C). See also Environmental Fate. 

APPLICATIONS

Biochemistry Steroid demethylation (ergosterol biosynthesis) inhibitor.  Mode of action Systemic fungicide with protective, curative, and eradicant action. Rapidly absorbed into the vegetative parts of the plant, with translocation principally acropetally.  Uses As a seed dressing, tebuconazole is effective against various smut and bunt diseases of cereals such as Tilletia spp., Ustilago spp., and Urocystis spp., also against Septoria nodorum (seed-borne), at 1-3 g/dt seed; and Sphacelotheca reiliana in maize, at 7.5 g/dt seed. As a spray, tebuconazole controls numerous pathogens in various crops including: rust species (Puccinia spp.) at 125-250 g/ha, powdery mildew (Erysiphe graminis) at 200-250 g/ha, scald (Rhynchosporium secalis) at 200-312 g/ha, Septoria spp. at 200-250 g/ha, Pyrenophora spp. at 200-312 g/ha, Cochliobolus sativus at 150-200 g/ha, and head scab (Fusarium spp.) at 188-250 g/ha, in cereals; leaf spots (Mycosphaerella spp.) at 125-250 g/ha, leaf rust (Puccinia arachidis) at 125 g/ha, and Sclerotium rolfsii at 200-250 g/ha, in peanuts; black leaf streak (Mycosphaerella fijiensis) at 100 g/ha, in bananas; stem rot (Sclerotinia sclerotiorum) at 250-375 g/ha, Alternaria spp. at 150-250 g/ha, stem canker (Leptosphaeria maculans) at 250 g/ha, and Pyrenopeziza brassicae at 125-250 g/ha, in oilseed rape; blister blight (Exobasidium vexans) at 25 g/ha, in tea; Phakopsora pachyrhizi at 100-150 g/ha, in soya beans; Monilinia spp. at 12.5-18.8 g/100 l, powdery mildew (Podosphaera leucotricha) at 10.0-12.5 g/100 l, Sphaerotheca pannosa at 12.5-18.8 g/100 l, scab (Venturia spp.) at 7.5-10.0 g/100 l, white rot in apples (Botryosphaeria dothidea) at 25 g/100 l, in pome and stone fruit; powdery mildew (Uncinula necator) at 100 g/ha, in grapevines; rust (Hemileia vastatrix) at 125-250 g/ha, berry spot disease (Cercospora coffeicola) at 188-250 g/ha, and American leaf disease (Mycena citricolor) at 125-188 g/ha, in coffee; white rot (Sclerotium cepivorum) at 250-375 g/ha, and purple blotch (Alternaria porri) at 125-250 g/ha, in bulb vegetables; leaf spot (Phaeoisariopsis griseola) at 250 g/ha, in beans; early blight (Alternaria solani) at 150-200 g/ha, in tomatoes and potatoes. Phytotoxicity Good plant compatibility in most crops with any formulation, and achieved in more sensitive crops by appropriate formulations, e.g. WP, WG or SC.  Formulation types DS; EC; ES; EW; FS; GF; SC; SE; WG; WP; WS.

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