UN PROCEDIMIENTO PARA LA PREPARACION DE UN COMPUESTO DE 3- FLUORALQUIL-DELTA CUADRADO-1, 2, 4-TRIAZOLIN-4-0 1-IL-VINIL-FOSFATO-1-0 4-SUSTITUIDO.

摘要

1390475 Unsaturated phosphates containing a 1,2,4-triazolin ring ELI LILLY & CO 3 July 1973 [19 July 1972 (2)] 31745/73 Headings C2P and C2C [Also in Division C5] The invention comprises compounds of the general formula wherein R8 is R4 or is the group A which is R9 is R10 or the group A with one and only one of R8 and R9 being the group A, X is O or S, R1 and R2 are independently Cl, Br, C 1 -C 2 alkyl or H, R3 is H, F, Cl, CF 3 or CHF 2 , R4 is C 1 -C 4 alkyl, C 3 -C 8 cycloalkyl or C 3 -C 4 alkenyl, R5 is C 1 -C 4 alkyl, the R5 radicals being identical, and R10 is R4, C 2 -C 6 dialkylamino, or wherein R6 and R7 are independently H, C 1 -C 4 alkyl or phenyl optionally monosubstituted with C 1 -C 3 alkyl, C 1 -C 3 alkoxy, halo, or C 1 -C 3 haloalkyl. They may be obtained by reacting wherein one n is zero and the other is 1 with an appropriately substituted acetic acid in the presence of dicyclohexylcarbodiimide or with an appropriately substituted acetyl chlorine in the presence of a base, and then reacting the product with an appropriate trialkyl phosphite. The products have pesticidal properties and may be used as active ingredients in pesticidal compositions of conventional type. The triazolin-5-thione compounds of Formula II may be obtained by ring closure of an appropriately 1,4 or 1,2-disubstituted thiosemicarbazide in basic aqueous solution and the triazolin-5-one compounds may be obtained either (a) by methylation of a triazolin-5-thione followed by oxidation of the resulting intermediate (III) with H 2 O 2 , or (b) by ring closure of an appropriately substituted semicarbazide by fusion. Examples are given for the production of 4 - methyl - 3 - trifluoromethyl - #2 - 1,2,4- triazolin - 5 - thione and the corresponding 5- one compound and 1-methyl-3-trifluoromethyl- #2 - 1,2,4 - triazolin - 5 - thione and the corresponding 5-one compound. Other compounds of Formula (II) obtainable in a similar manner are also specified. 4 - Methyl - 1 - trifluoroacetyl thiosemicarbazide is obtained by reacting trifluoroacetyl fluoride with 4-methylthiosemicarbazide in methylene chloride in the presence of pyridine. 4 - Methyl - 3 - trifluoromethyl - 5 - methylthio- 1H -1,2,4 - triazole is obtained by reacting the corresponding substituted #2-1,2,4-triazoline-5- thione dissolved in methanol with NaOCH 3 and then with methyl iodide. The analogous 1- methyl - 3 - trifluoromethyl - 5 - methylthio - 1H- 1,2,4-triazole is obtained similarly from the corresponding-5-thione.