Abstract:
To develop new fungicides with phloem mobility, a series of
N-phenylaminopyrimidine acid and amino acid derivatives were designed and synthesized. All target compounds were characterized by
1H NMR,
13C NMR and HRMS. The antifungal activities of all target compounds were tested
in vitro and the phloem mobility were assayed in the castor bean seedling system. The results of the antifungal activity showed that most of the target compounds exhibited good antifungal activities against
Bortrytis cinerea,
Colletotrichum gloeosporioides,
Sclerotinia sclerotiorum,
Bipolaris maydis and
Phytophthora parasitica at a concentration of 50 μg/mL. In particular,
6b(L),
6c(L) and
6d(L) showed an inhibition rate of more than 60% against
B. cinerea, which was equivalent to that of the commercial fungicide pyrimethanil (60.78%). Among them, compound
6b(L) showed the best antifungal activity, with an EC
50 value of 19.96 μg/mL, superior to pyrimethanil (38.82 μg/mL). Furthermore,
5a, 6b(D), 5d(D),
5e(L) and
5j(L) showed excellent antifungal activities against
S. sclerotiorum, with the inhibition rates of more than 80%. The results of the phloem mobility test showed that the amino acidification of pyrimethanil was effective in endowing the target compound with phloem mobility, among which
methyl (6-methyl-2-(phenylamino) pyrimidine-4-carbonyl)-D-alanine showed the best phloem mobility. When the concentration of
methyl (6-methyl-2-(phenylamino)pyrimidine-4-carbonyl)-D-alanine in incubation solution was 50 μg/mL, the concentration was 22.28 μg/mL in phloem sap after 2-4 h. Meanwhile, it was also found that
N-phenylaminopyrimidine acid and
L-amino acid derivatives were easily hydrolyzed to release the precursor
N-phenylaminopyrimidine acid after being absorbed by castor bean cotyledons, but
N-phenylaminopyrimidine acid and
D-amino acid derivatives weren't hydrolyzed. In this study, some new fungicide candidates with both good antifungal activity and phloem mobility were successfully obtained, which can provide a basis for the development of new phloem mobility fungicides.