Photochemistry of pesticides, 3: Photolysis of methyl 2-benzimidazolecarbamate (Carbendazim) in the presence of singlet oxygen

The photolysis of methyl 2-benzimidazolecarbamate (Carbendazim, $\text{1}$) in methanol and in the presence of singlet oxygen, was studied. Dimethyl oxalate $\text{4}$, 2-aminobenzimidazole $\text{7}$, benzimidazole $\text{9}$, N,N′-dicarbomethoxyguanidine $\text{13}$, monocarbomethoxyguanidine $\text{14}$, monocarbomethoxyurea $\text{15}$, and 2-guanidinobenzimidazole $\text{17}$, were isolated and identified in this reaction.A mechanism that accounts for the formation of the photoreaction products, is presented.