Synthesis and herbicidal activity of isoindoline-1,3-dione substituted benzoxazinone derivatives containing a carboxylic ester group.

A carboxylic ester group was introduced to three series of isoindolinedione substituted benzoxazinone derivatives. Some of these analogues exhibited good herbicidal activities, and the injury symptoms against weeds included leaf cupping, crinkling, bronzing, and necrosis, typical of protox inhibitor herbicides. Structurally, they were classified as Chemical Group A (4-carboxylic ester group-6-isoindolinyl-benzoxazinones), B (4-carboxylic ester group-7-isoindolinyl-benzoxazinones), and C (4-carboxylic ester group-6- tetrahydroisoindolinyl-benzoxazinones).

3-tert-Butyl-4-oxo-3,4-dihydro-phthalazin-1-yl 3,5-dimethyl-benzoate.

The title compound, C(21)H(22)N(2)O(3), was synthesized by the reaction of tert-butyl-hydrazine with phthalic anhydride and further O-benzoyl-ation of the resulting inter-mediate by 3,5-dimethyl-benzoyl chloride. Inter-molecular C-H⋯O=C inter-actions link the mol-ecules into layers.

Synthesis and herbicidal activity of 2-(7-fluoro-3-oxo- 3,4-dihydro-2H-benzo[b][1,4]oxazin-6-yl)isoindoline-1,3-diones.

The mode of action of 2-(7-fluoro-3-oxo-3,4-dihydro-2H-benzo[b][1,4]oxazin-6-yl)-4,5,6,7-tetrahydro-2H-isoindoline-1,3-diones, including the commercial herbicide flumioxazin, had been identified as inhibition of protoporphyrinogen oxidase (protox). As part of continuous efforts to search for new herbicides with high efficacy, broad-spectrum activity, and safety to crops, flumioxazin and its iodo analogue (B2055) were used as lead compounds for further optimization. Series of novel compounds were prepared by multistep synthetic procedures starting from 5-fluoro-2-nitrophenol.