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  1. 1. Heterocyclic Sulfur Compounds 737 Carboxin Uses : fungicide, cereals, maize, cotton, peanuts, soyabeans Trade names: Vitavax (Uniroyal) Type : oxathiin, amide Synthes is : I ---- C ~ C ..~.. C--. 0...,--. C~ 0 I N O II i i / c----c----c~ c-- N !II t o aceto acetanilide diketene aniline sulfuryl S02C12 chloride O II t i c---c------c---c--- N/ I II t o I--e- l I Ott KOH ~0-~-~'-~I I me rcap to ethanol 0 II I t C - - C - - C - - C - - N/ I Ii f C1 o NaOHI /~ -C- I ,~ // C C O /x C / carboxin
  2. 2. 738 Pesticides Synthesis Handbook alternate route : o I I fl --C--C--C--C I II I I i 0 O--C--C-- I I O + S02C12-----@ --c--c--c--c + o I o--c--c- w I ethyl aceto sul furyl acetate chloride Ho--cl--cI-c'SH I I KOH 0 s I // --C--C--C--C 0 O--C--C-- I i I-c- --C-- tOH I -C- I o% ~= C--C 0 / S c~ / c / SOCI 2 thionyl chloride NaOH I -e- l O C ~-=//o/ .o I I C / / N aniline I -e- l O ,,/,U / carboxin