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The antimicrobial agent pramanicin ( 1 ), and a related fatty acid ( 6 ), were isolated from a corn-based solid or a lactose-containing liquid fermentation of a sterile fungus found growing in grass. The structures of these compounds were determined by a variety of spectral means including UV, IR, and NMR spectroscopy, as well as mass spectrometry. A number of chemical derivatives are also presented here. Pramanicin represents a new class of antimicrobial agents containing a highly functionalized head group and functionalized fatty side chain

Seven unconjugated allenic anilides with the allenic moiety situated at the 3, 4 position were synthesized and evaluated for acaricidal activity against Boophilus microplus (Canestrinii). The order of toxicity (% adult mortality) of the anilides against adult B. microplus at 0.5 μg tick−1 was: N-(3-chloro-4-methyl-phenyl)-5-methylhexa-3, 4-dienamide, (I) = N-(4-bromophenyl)-5-methylhexa-3, 4-dienamide(III)(100%) > N-(4-bromophenyl)-deca-3, 4-dienamide (VI)(68%) > N-(3, 4-dichlorophenyl)-5-methylhexa-3, 4-dienamide (II) (32.3%) > N-(3, 4-dichlorophenyl)-5-methylhepta-3, 4-dienamide (IV) (28%) > N-(3-chloro-4-methylphenyl)-5-ethylhepta-3, 4-dienamide (VII) (24%) > N-(4-bromophenyl)-5-methylhepta-3, 4-dienamide (V) (20%). Comparison of the relative potencies (in parenthesis) at 1.5 μg tick−1 of the anilides with three commercial acaricides: pyrenone, lindane and carbaryl, revealed the following orders of activities: in comparison with pyrenone: pyrenone = I = II (1) > VI(0.93) > II (0.67) > IV (0.55) > VII (0.46) > VI (0.37); in comparison with lindane: I = HI (6.06) > VI (5.65) > II (4.04) > IV (3.36) > VII (2.76) > V (2.39) > lindane (1.0). All anilides were more toxic than carbaryl which gave no mortality at 1.5 μg tick−1. The need for developing more effective control agents for B. microplus is highlighted by the high levels of resistance found in some Jamaican populations of the pest. Resistance of the orders of 31- to 227-fold had been reported against lindane and between 15- and 67-fold to carbaryl.