5-Ethoxy-3-trichloromethyl-1,2,4-thiadiazol

The excellent pesticidal and fungicidal properties of 5-ethoxy-3-trichloromethyl-1,2,4-thiadiazole (363) are well known <82AHC(32)285). It is a commercial product and is marketed under a variety of names of which Terrazole is the most common. Since 1984, a variety of 1,2,4-thiadiazole derivatives have been found to possess fungicidal activity. Thus, compounds such as (364), (365), and (366) and... 

Ethoxyquin Ethoxyquine. See 6-Ethoxy-1,2-dihydro-2,2,4-trimethylquinoline Ethoxysilane. See Ethyl silicate 5-Ethoxy-3-trichloromethyl-1,2,4-thiadiazole. 

Terracoat (mixture of 5-ethoxy-3-(trichloromethyl)-1,2,4-thiadiazole with pentachloronitrobenzene) Molecular formula C5H5CI3N2OS. C5CI5NO2 Text Descriptor MX... 

Ethoxy-3-trichloromethyl-l,2,4-thiadiazole has excellent pesticidal and fungicidal properties. It is a commercial product, whose most common trade name is Terrazole. 

Chemical Name 5-ethoxy-3-(trichloromethyl)-l,2,4-thiadiazole ethyl 3-trichloromethyl-l,2,4-thiadiazolyl ether Uses as fungicide for control of Phytophthora and Pythium spp. in cotton, ornamentals, vegetables, groundnuts, cucurbits, tomatoes, and other crops also used as a nitrification inhibitor in maize, cotton and wheat. 

In a variation of this synthesis, the amidine is N-halogenated prior to its condensation with an isothiocyanate ester the resulting IV-haloimidoyl-thioureas (238) are readily cyclized to 239 by alkalis. By employing bromine in conjunction with methylene chloride-aqueous alkali as the reaction medium, the reaction may be performed in one operation. 3-Trichloromethyl-5-(substituted)amino-l,2,4-thiadiazoles have been produced by this method.187 The use of potassium ethyl xanthate similarly yields the 5-ethoxy analogs (240 e.g., R = CC13, R1 = Et) directly, with elimination of the elements of hydrogen sulfide.188... 

The preparation of 5-ethoxy-3-trichloromethyl-l,2,4-thiadiazole was first reported3,471 in 1962, and its excellent pesticidal properties publicized shortly afterwards 472 Since then its effectiveness and usefulness as a systemic soil fungicide have been proved in a large number of trials. It has become firmly established in agricultural practice, and is known under a variety of commercial names,473,474 Terrazole being the most common. Numerous... 

Ethoxy-3-trichloromethyl-l,2,4-thiadiazole (Registry No. 2593-15-9) appears in the Literature under the following names OM-2424, Terrazole, Truban, ETMT, Terracoat L 21, Koban, Aaterra, Etridiazole, Ethazole, Pansoil (Japan), Echlomezole (Japan). 

Mixtures of 5-ethoxy-3-trichloromethyl-l,2,4-thiadiazole and pentachloronitrobenzene (Registry No. 8065-61-0) are named Terracoat, Terrachlor-Super X. Other mixtures have been used less frequently. 

Terrazole 1,2,4-Thiadiazole, 6-ethoxy-3-(trichloromethyl)- C5H5CI3N2OS 2693-16-9 247.630 19.9 96 I.6O335 ... 

Although the 1,2,4-thiazole moiety does not occur in natural products, many synthetic derivatives are biologically active and are used as insecticides, fungicides, herbicides and antibacterials. For instance, 5-ethoxy-3-trichloromethyl-l,2,4-thiadiazole (etridiazole) is used to combat or prevent fungal infestation of plants, fruit, cotton, seeds and soil [149]. 

Biological Activity.—5-Ethoxy-3-(trichloromethyl)-l,2,4-thiadiazole controls root rot (caused by Phytophthora cinnamomi) in plants such as Chamaecyparis lawsoniana and Eucalyptus marginata. ... 

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