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14 Fungicides, Agricultural
local systemic activity. It is used mainly for con-
trol of apple scab but also for fruit rot ...
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Ullmann agricultural fungicides p.14

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Ullmann agricultural fungicides p.14

  1. 1. 14 Fungicides, Agricultural local systemic activity. It is used mainly for con- trol of apple scab but also for fruit rot and leaf spot diseases of deciduous fruit and nuts. Trade Names. Cyprex, Venturol, Melprex (Cyanamid, Rhˆone-Poulenc); Dodene (Sipcam). Dithianon [3347-22-6], 5,10-dihydro-5,10- dioxonaphtho-[2,3-b]-1,4-dithiin-2,3-dicarbo- nitrile, C14H4N2O2S2, Mr 296.3, mp 225 ◦ C, vapor pressure 66 µPa at 25 ◦ C, consists of brown crystals which are practically insolu- ble in water and only slightly soluble in organic solvents [9, p. 225], [13, p. 105]. Dithianon is produced by reaction of hy- drogen cyanide with carbon disulfide in di- methylformamide to yield dimercaptomaleic acid dinitrile; this intermediate is then treated with 2,3-dichloronaphthoquinone [40]. Dithianon (announced in 1963) is a protective contactfungicidewithabroadspectrumofactiv- ity against, for example, leaf and fruit spot dis- eases, downy mildew, late blight, anthracnose, and rust. It is relatively expensive and is used on crops (e.g., deciduous fruit trees and coffee) only when it produces significant benefits that are not obtained with cheaper contact fungicides such as dithiocarbamates. Trade Names. Actuan, Delen (Cyanamid); Clus- ter (Barclay). Chlorothalonil [1897-45-6], tetra- chloroisophthalonitrile, C8Cl4N2, Mr 265.9, mp 250 –251 ◦ C, bp 350 ◦ C, vapor pressure 1.3 Pa at 40 ◦ C, consists of colorless crystals which are practically insoluble in water but slightly soluble in organic solvents such as acetone, cy- clohexanone, and xylene [9, p. 120], [13, p. 91], [14, p. 163]. Chlorothalonil is produced by reaction of tetrachloroisophthalyl chloride with ammonia to give the diamide which, on treatment with phos- phorus oxychloride, yields the dinitrile [41]. Chlorothalonil (announced in 1964) has a broad spectrum of activity and is used as a pre- ventative foliar fungicide on a wide range of crops including vegetables, turf, top fruit, cof- fee, groundnuts, and cereals. It is relatively ex- pensive and is usually used on more valuable cultures. Trade Names. Bravo (ISK Biosciences); Da- conil (SDS Biotech, Zeneca, ISK Biosciences). Etridiazole [2593-15-9], 5-ethoxy-3-tri- chloromethyl-1,2,4-thiadiazole,C5H5Cl3N2OS, Mr 247.5, mp 20 ◦ C, bp 95 ◦ C at 0.13 kPa, vapor pressure 13 mPa at room temperature, is a yel- low liquid with a persistent odor; it is practically insoluble in water but soluble in many organic solvents [9, p. 252], [14, p. 219], [15, p. 397]. Etridiazole is produced by reaction of trichloroacetamidine hydrochloride with trichloromethanesulfenyl chloride and then with sodium hydroxide in ethanol [42]. Etridiazole (announced in 1969) is a soil fungicide with preventative and curative prop- erties. It is effective against Phytophthora and Pythium spp. and is used on turf, ornamentals, vegetables, avocados, and other crops. It can be applied to the soil surface or mixed with the soil prior to planting. Trade Name. Terrazole (Uniroyal). Phthalide [27355-22-2], 4,5,6,7-tetra- chlorophthalide, C8H2Cl4O2, Mr 271.9, mp 209 – 210 ◦ C, consists of colorless crystals which are practically insoluble in water and only slightly soluble in organic solvents [9, p. 517], [14, p. 197]. Phthalide is produced by treatment of 1,2- bis(dichloromethyl)-3,4,5,6-tetrachloroben- zene with 75 % sulfuric acid [43].

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