ALBERT D. SWENSEN AND WARREN E. WEAVER
4060
Vol. 70
[CONTRIBUTION FROM TIfB; CHEMISTRY DIVISIONOF THE NAVALRESEARCH LABORATORY]
Organic Fungicides. III. The Preparation of Some apDichloroacetamides BY ALBERT D. S ~ N S E AND N ' WARREN E. WEAVER
The previous papers of this series described the preparation of a-bromoacetyl and a-bromopropionyl derivatives of a number of aliphatic amines2 In order to investigate systematically the fungicidal activit.y of the a-halo amides, the synthesis of similar a,a-dichloroacetamides was undertaken.
The lower members of the series possess a camphoraceous odor and exhibited no lachrymatory or other irritating properties. The N-methyl and N-ethyl compounds were recrystallized from water; the other solids from water and ethanol. All the compounds were white when pure.
TABLE 1
O R
H
I
~,~-DICHLOROACETAMIDES, Cl-C-C-N
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cI1 !tI' These substances were all prepared by Method I except the first three members of the Series, which were prepared by Method 11. Yield, B. p.,= M. p MR Nitrogen % * %
OC. 72 98 HCH176 97 CHICHIH77 104 CZHK85 100 CZHKCZHK89 111 Hn-CaHi81 87 n-CaHin-CaHiH45 iso-CaH7iso-C~H762 75 iso-CaHi87 93 HCHzs CH-CHzH74 88 n-GHr 78 109 n-CaHir n-OHp H71 87 i SO-CIHO iso-CtHr 58 92 ISO-CIHOH59 91 CHsCHzCH(CHa)CH:CHL!H ( CHs) . 57 101 CHaCHzCH(CHd77 95 Hn-CrHr 78 121 n-CsHr *
