Synthesis and Herbicidal Activity of 1H-1,4-Benzodiazepine-2,5-diones

Abstract

A series of 1H-1,4-benzodiazepine-2,5-diones, which have been found to inhibit photosystem II electron transport, were evaluated for their herbicidal activity. Many of the analogues tested exhibited moderate to good herbicidal activity both preemergence and postemergence. The structure-activity relationships were probed by substitution in both the benzene and diazepine ring. Among the variations investigated, it was found that maximal herbicidal activity was obtained by substitution at C-7 and C-9 in the aromatic portion and by bulky aliphatic substitution at N-4 while leaving N-1, C-6, and C-8 unsubstituted.

Biosynthesis, synthesis, and biological activities of pyrrolobenzodiazepines

“…Some members of the second group, 1,4‐benzodiazepine‐2,5‐ones, have been tested as panxiolytic and anticonvulsant, as well as peptidomimetic inhibitors , . In addition to their medicinal properties, they also possess herbicidal activity . Cyclopenin, the only naturally produced 1,4‐benzodiazepine‐2,5‐one isolated, is particularly interesting as the biosynthetic intermediate of viridicatin, an inhibitor of replication of HIV .…”

“…4,5 In addition to their medicinal properties, they also possess herbicidal activity. 6 Cyclopenin, the only naturally produced 1,4-benzodiazepine-2,5-one isolated, is particularly interesting as the biosynthetic intermediate of viridicatin, 7 an inhibitor of replication of HIV. 8 The naturally produced TLN-4601 (formerly ECO-4601) is the sole member of the dibenzodiazepinones' group, 9 with a broad spectrum of antitumor activity in cancer cells and human xenografts.…”

SYNTHESIS OFN-(MORPHOLINOMETHYL) BENZAMIDES AS MOCLOBEMIDE ANALOGS

“…The synthesis of our analogs started with the classical reaction of substituted benzoyl chlorides 2(a-d) with glycine hydrochloride 8,9 to afford the ethyl esters of hippuric acids 3(a-d) (Scheme 1).…”

Synthesis and Herbicidal Activity of N-Oxide Derivatives

“…Evaluations were conducted until two to three true leaves were present after application (∼2 weeks after treatment). Results of the greenhouse herbicide evaluation were expressed on a 0-4 rating scale (Eussen et al, 1990;Joshi et al, 1990;Karp et al, 1997). The scale is based on the determination of the decreasing of the following parameters: length of first leaf (lfl), aerial weight (aw), and radicular weight (rw) compared to those of an untreated control (with only carrier).…”