Process for producing 1-[2-(2,4-dichlorophenyl)-pentyl]-1H-1,2,4

Details Process for producing 1-[2-(2,4-dichlorophenyl)-pentyl]-1H-1,2,4 Process for producing 1-[2-(2,4-dichlorophenyl)-pentyl]-1H-1,2,4

1983-06-16

1985-12-03

Rollins, Alton D.

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

560 34, 564 34, 564 36, 564149, 564151, 564251, 564313, C07D24908

Patent

active

045567174

ABSTRACT:
1-[2-(2,4-Dichlorophenyl)-pentyl]-1H-1,2,4-triazole can be produced, in a novel, simple, economical and isomer-free form, by reacting 2-(2,4-dichlorophenyl)-valeronitrile, in the presence of hydrogen, an acid and a hydrogenation catalyst, with a compound H.sub.2 N--NH--R to a compound of the formula ##STR1## hydrogenating the compound (III) catalytically to a compound ##STR2## hydrolysing compounds (IV) wherein R is not hydrogen, and converting the compounds (IV) wherein R=H, or salts thereof, with formamide and/or [3-(dimethylamino)-2-azaprop-2-en-1-ylidene]-dimethylammonium chloride, into 1-[2-(2,4-dichlorophenyl)-pentyl]-1H-1,2,4-triazole, or converting compounds (IV) wherein R=--COR', with aqueous formic acid, into the corresponding N,N'-bisformyl derivatives, and reacting these with formamide, optionally in the presence of NH.sub.3, to 1-[2-(2,4-dichlorophenyl)-pentyl]-1H-1,2,4-triazole. R in the formulae is hydrogen, --CHO, --COR', --COOR' or --CONH.sub.2, and R' is C.sub.1 -C.sub.4 -alkyl, benzyl or phenyl.
1-[2-(2,4-Dichlorophenyl)-pentyl]-1H-1,2,4-triazole exhibits fungicidal activity, and can be used to control phytopathogenic fungi.

REFERENCES:
patent: 2885399 (1959-05-01), Omietanski
patent: 2909567 (1959-10-01), Rudner
patent: 3197474 (1965-07-01), Biel
patent: 3197501 (1965-07-01), Biel
patent: 3213138 (1965-10-01), Biel
patent: 3359316 (1967-12-01), Biel
Elderfield, Heterocyclic Compounds, vol. 7, (New York, 1961), pp. 433-434, 440-441.
Pleininger et al., Chem. Ber., 88, 1956 (1955).

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