Substituted 1-aryl-2-napthoylamines and their use as microbicide

Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Heterocyclic carbon compounds containing a hetero ring...

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514212, 514319, 514321, 514422, 514423, 514452, 514463, 514464, 514465, 540450, 540480, 540483, 540607, 546205, 546206, 546197, 548526, 548539, 544 584, 544161, 544176, 544248, 544377, 544391, 549441, 564 74, 564172, C07D23304, C07D21106, C07D29510, A61K 3140, A61K 31445, A61K 3155

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049686771

ABSTRACT:
1-Aryl-2-naphthoylamines of formula I are described ##STR1## wherein R.sub.1 is halogen, nitro, cyano, C.sub.1 -C.sub.6 alkyl that is unsubstituted or mono- or poly-substituted by halogen and/or C.sub.1 -C.sub.3 alkoxy, or is C.sub.3 -C.sub.6 cycloalkyl, OR.sub.4, NR.sub.5 R.sub.6, CO2R.sub.5, CONR.sub.5 R.sub.6 or NHCOR.sub.7, or wherein two adjacent positions in the nucleus are bridged by a methylenedioxy or ethylenedioxy group that is unsubstituted or mono- or poly-substituted by fluorine, wherein further R.sub.4 is hydrogen or C.sub.1 -C.sub.6 alkyl that is unsubstituted or substituted by C.sub.1 -C.sub.3 alkoxy or mono- or poly-substituted by halogen, or is C.sub.3 -C.sub.4 alkenyl, 2-propynyl, 3-halo-2-propynyl, ##STR2## or COR.sub.7, each of R.sub.5 and R.sub.6, independently of the other, is H or C.sub.1 -C.sub.4 alkyl, R.sub.7 is C.sub.1 -C.sub.4 alkyl and Z is O or NH, a and b denote the number of occupied positions in the respective 6-membered ring, and a is a number from 1 to 3 and b is a number from 0 to 3, the individual groups R.sub.1 being identical or different when the sum of a and b is greater than 1, X is O, S or NH, each of R.sub.2 and R.sub.3, independently of the other, is C.sub.1 -C.sub.6 alkyl that is unsubstituted or substituted by C.sub.1 -C.sub.4 alkoxy, halogen or by cyano, or is C.sub.3 -C.sub.7 cycloalkyl, C.sub.3 -C.sub.7 alkenyl or the radical ##STR3## wherein n is 0 or 1, or R.sub.2 and R.sub.3 are also together a C.sub.4 -C.sub.7 alkylene chain that together with the nitrogen atom may form a heterocycle that is unsubstituted or mono- or di-substituted by C.sub.1 -C.sub.4 alkyl, it being possible for one of the methylene groups in this chain to be replaced by O, S or NR.sub.7, and for R.sub.2 also to be hydrogen.
The compounds of formula I have microbicidal activity and can be used advantageously for plant protection.

REFERENCES:
patent: 4499094 (1985-02-01), Dubroeucq et al.
Indian J. Pharm. Sci., 47(1), 12-15 (1985).
J. Chem. Soc. Perkin Trans. I, 1360-1366 (1978).
Chem. Abstract, vol. 110:1352494 (1989), Curtze et al., DE 3,710,717.

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