N-aminopyridone derivatives and their use as herbicides

Plant protecting and regulating compositions – Plant growth regulating compositions – Organic active compound containing

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5462837, 546300, 549323, 549324, 549325, C07D21198, C07D21389, C07C 5948, A01N 4340

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060280336

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BRIEF SUMMARY
The present invention relates to N-aminopyridone derivatives of the formula I: ##STR2## where the substituents have the following meanings: R.sup.1 -R.sup.5 can be identical or different substituents: (CH.sub.2).sub.m SO.sub.n R.sup.16, ZCOR.sup.17, NR.sup.20 SO.sub.n R.sup.13, OSO.sub.n R.sup.13, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -alkylamino, C.sub.1 -C.sub.3 -dialkylamino, C.sub.2 -C.sub.4 -alkenyl, C.sub.2 -C.sub.4 -alkynyl, it being possible for the carbon radicals to be unbranched or branched and to -have attached to them in each case one to five halogen atoms and/or one to two of the following groups: alkoxy, alkylthio, cyano, nitro; having five ring members, it being possible for the ring carbon atom to be substituted by one to two halogen atoms; -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxyalkyl, C.sub.1 -C.sub.4 -haloalkyl; -cycloalkyl, (CH.sub.2).sub.m SO.sub.n R.sup.16, C.sub.2 -C.sub.4 -alkynyl, C.sub.2 -C.sub.4 -alkenyl, it being possible for the carbon radicals to be unbranched or branched and to have attached to them in each case one to five halogen atoms and/or one to two of the following groups: alkoxy, alkylthio, nitro, cyano; to it one to three of the following radicals: halogen, nitro, cyano, unbranched or branched C.sub.1 -C.sub.3 -alkyl, C.sub.1 -C.sub.3 -alkoxyalkyl or C.sub.1 -C.sub.3 -haloalkyl, OCN, SCN; following substituents: halogen, nitro, cyano, unbranched or branched: C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -alkoxyalkyl, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -alkylamino, C.sub.1 -C.sub.4 -dialkylamino, C.sub.1 -C.sub.4 -alkylcarbonyloxyalkyl, OCN, SF.sub.5, SCN, (CH.sub.2).sub.m SO.sub.n R.sup.16, NSO.sub.n R.sup.13, OSO.sub.n R.sup.13, ZCOR.sup.17 ; ##STR3## a 5-membered saturated, unsaturated or aromatic heterocycle having one to four nitrogen atoms or one to three nitrogen atoms and additionally one sulfur or oxygen atom in the ring, which can have attached to it one to three halogen atoms and/or one to three of the following radicals: nitro, cyano, alkyl, alkoxy, alkylthio, haloalkyl, haloalkoxy, ZCOR.sup.17 ; halogen atoms and/or one to three of the following radicals: nitro, cyano, alkyl, alkoxy, alkylthio, haloalkyl, haloalkoxy, ZCOR.sup.17 ; four nitrogen atoms or one to three nitrogen atoms and additionally one sulfur or oxygen atom in the ring, which can have attached to it one to three halogen atoms and/or one to three of the following radicals: nitro, cyano, alkyl, alkoxy, alkylthio, haloalkyl, haloalkoxy, ZCOR.sup.17 ; -cycloalkyl. by two identical or different substituents R.sup.14 ; by the radicals R.sup.23 and R.sup.24 ; R.sup.11 and R.sup.12 are part of a 5- or 6-membered saturated, unsaturated or aromatic heterocycle which is bonded via nitrogen and has one to four nitrogen atoms or one to three nitrogen atoms and additionally one sulfur or oxygen atom in the ring, which has attached to it one to three halogen atoms and/or one to three of the following radicals: oxo, nitro, cyano, alkyl, alkoxy, alkylthio, haloalkyl, haloalkoxy; possible for the carbon radicals to be unbranched or branched and to have attached to them in each case one to five halogen atoms and/or one to two of the following groups: alkoxy, alkylthio, cyano, nitro; -cycloalkyl, C.sub.2 -C.sub.6 -alkynyl, C.sub.2 -C.sub.6 -alkenyl, it being possible for the carbon radicals to be unbranched or branched and to have attached to them in each case one to five halogen atoms and/or one to two of the following groups: OH, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -alkoxyalkyl, alkylthio, cyano, substituted or unsubstituted phenyl, nitro, ZCOR.sup.17 ; following substituents: halogen, nitro, cyano, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -alkoxyalkyl, C.sub.1 -C.sub.4 -alkylamino, C.sub.1 -C.sub.4 -dialkylamino, it being possible for the alkyl radicals to be unbranched or branched, OCN, SCN, OH, (CH.sub.2).sub.m SO.sub.n R.sup.16, NSO.sub.n R.sup.13, OSO.sub.n R.sup.13, ZCOR.sup.

REFERENCES:
patent: 4152136 (1979-05-01), Taylor
patent: 5234895 (1993-08-01), Felix
Synthesis, No. 10, 1974, p. 717-719.
Pat. Abst. of Japan, vol. 6, No. 44 (C-095), Mar. 19, 1982 (English abstract of JP 56 161348).
Organic Synthesis, Voll. I vol II. 1946, pp. 81-83, XP002009451.
Cignarella, Eur. J. Med. Chem., 30, 9, 1995, pp. 721-726.

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