TY - JOUR
T1 - Preparation, proton and carbon‐13 structure determination, and fungicidal activity of chlorinated 1‐arylamino‐1H‐pyrrole‐2,5‐diones
AU - Yaroslavskym, Carmela
AU - Bracha, Peretz
AU - Glaser, Robert
PY - 1989/1/1
Y1 - 1989/1/1
N2 - 1‐(2′,4′‐dichloro)phenylamino‐1H‐pyrrole‐2,5‐dione and 1‐(2′,4′,6′‐trichloro)phenylamino‐1H‐pyrrole‐2,5‐dione were prepared via direct chlorination of 2‐phenyl‐3‐oxo‐6‐hydroxy‐2H‐pyridazine. Both pmr and mass spectroscopy clearly showed that dichloro substitution occurred in the aromatic moiety and not in the vinylic region of the molecule. The former method showed that pyridiazine‐ to pyrrole‐ring isomerization had occurred already at the level of dichlorination. The identical 2′,4′‐dichlorophenyl and 2′,4′,6′‐trichlorophenylpyr‐rolediones were also prepared by reaction of maleic anhydride with the appropriate arylhydrazine. Similar 2′,4‐dichlorophenyl and 2′,4′,6′‐trichlorophenyl analogues were prepared using dichloromaleic anhydride. Cmr spectroscopic techniques were used for pyridazine‐/pyrrole‐ring stereochemical assignment of products derived from dichloromaleic anhydride. 1‐(2′,4′‐dichloro)phenylamino‐1H‐pyrrole‐2,5‐dione and the trichloro‐phenyl analogue were shown to exhibit fungicidal activity in both in‐vivo and in‐vitro assays.
AB - 1‐(2′,4′‐dichloro)phenylamino‐1H‐pyrrole‐2,5‐dione and 1‐(2′,4′,6′‐trichloro)phenylamino‐1H‐pyrrole‐2,5‐dione were prepared via direct chlorination of 2‐phenyl‐3‐oxo‐6‐hydroxy‐2H‐pyridazine. Both pmr and mass spectroscopy clearly showed that dichloro substitution occurred in the aromatic moiety and not in the vinylic region of the molecule. The former method showed that pyridiazine‐ to pyrrole‐ring isomerization had occurred already at the level of dichlorination. The identical 2′,4′‐dichlorophenyl and 2′,4′,6′‐trichlorophenylpyr‐rolediones were also prepared by reaction of maleic anhydride with the appropriate arylhydrazine. Similar 2′,4‐dichlorophenyl and 2′,4′,6′‐trichlorophenyl analogues were prepared using dichloromaleic anhydride. Cmr spectroscopic techniques were used for pyridazine‐/pyrrole‐ring stereochemical assignment of products derived from dichloromaleic anhydride. 1‐(2′,4′‐dichloro)phenylamino‐1H‐pyrrole‐2,5‐dione and the trichloro‐phenyl analogue were shown to exhibit fungicidal activity in both in‐vivo and in‐vitro assays.
UR - http://www.scopus.com/inward/record.url?scp=0024949421&partnerID=8YFLogxK
U2 - 10.1002/jhet.5570260626
DO - 10.1002/jhet.5570260626
M3 - Article
AN - SCOPUS:0024949421
SN - 0022-152X
VL - 26
SP - 1649
EP - 1654
JO - Journal of Heterocyclic Chemistry
JF - Journal of Heterocyclic Chemistry
IS - 6
ER -