Aminopyrazinones and aminotriazinones

Details Aminopyrazinones and aminotriazinones Aminopyrazinones and aminotriazinones

1989-07-25

1990-04-24

Shen, Cecilia

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

Organic compounds

Four or more ring nitrogens in the bicyclo ring system

544405, 544408, 71 92, 71 93, C07D25308, A01N 4348, A01N 4364

Patent

active

049202235

ABSTRACT:
Aminopyrazinones and aminotriazinones of the formula I ##STR1## and the salts of these compounds with amines, alkali metal or alkaline earth metal bases or quaternary ammonium bases have good pre- and post-emergent selective herbicidal and growth-regulating properties. In this formula, E is nitrogen or .dbd.CR.sup.4 --, R.sup.1 is C.sub.1 -C.sub.4 -alkyl, R.sup.2 is hydrogen, C.sub.1 -C.sub.3 -alkyl, C.sub.1 -C.sub.3 -halogenoalkyl, C.sub.1 -C.sub.3 -alkoxy, C.sub.1 -C.sub.3 -halogenoalkoxy, C.sub.1 -C.sub.3 -alkylthio, C.sub.1 -C.sub.3 -alkylsulfinyl, C.sub.1 -C.sub.2 -alkoxyethoxy, C.sub.1 -C.sub.3 -alkylsulfonyl, halogen or --NR.sup.5 R.sup.6, R.sup.3 is hydrogen or C.sub.1 -C.sub.3 -alkyl and Q is a group ##STR2## in which R.sup.4 is hydrogen, C.sub.1 -C.sub.3 -alkyl, C.sub.1 -C.sub.3 -halogenoalkyl, C.sub.1 -C.sub.3 -alkoxy, cyclopropyl, C.sub.1 -C.sub.3 -halogenoalkoxy, C.sub.1 -C.sub.3 -alkylthio, C.sub.2 -C.sub.4 -alkoxyalkyl, C.sub.3 -C.sub.5 -dialkoxymethyl, halogen or --NR.sup.5 R.sup.6, R.sup.5 and R.sup.6 independently of one another are hydrogen or C.sub.1 -C.sub.3 -alkyl, X is oxygen or sulfur and A is a group ##STR3## in which Y is oxygen, sulfur, --CH.dbd.CH--, --NR.sup.9 -- or --CR.sup.10 .dbd.N--, R.sup.7 is hydrogen, halogen, C.sub.1 -C.sub.3 -alkyl, C.sub.1 -C.sub.3 -alkoxy, nitro or trifluoromethyl, R.sup.8 is hydrogen, halogen, C.sub.1 -C.sub.3 -alkyl, C.sub.1 -C.sub.3 -alkoxy, nitro, --C.tbd.CH, or one of the groups ##STR4## R.sup.9 and R.sup.10 independently of one another are hydrogen, C.sub.1 -C.sub.3 -alkyl or C.sub.2 -C.sub.4 -alkenyl, R.sup.11 is hydrogen, C.sub.1 -C.sub.3 -alkyl, C.sub.1 -C.sub.3 -halogenoalkyl, C.sub.3 -C.sub.6 -cycloalkyl or C.sub.2 -C.sub.4 -alkoxyalkyl, R.sup.12 is C.sub.1 -C.sub.6 -alkoxy, C.sub.3 -C.sub.6 -alkenyloxy, C.sub.3 -C.sub.6 -alkinyloxy, C.sub.2 -C.sub.6 -halogenoalkoxy, C.sub.1 -C.sub.4 -cyanoalkoxy, C.sub.1 -C.sub.6 -alkylthio, C.sub.3 -C.sub.6 -alkenylthio, C.sub.3 -C.sub.6 -alkinylthio, C.sub.5 -C.sub.6 -cycloalkoxy, C.sub.2 -C.sub.6 -alkoxyalkoxy or --NR.sup.16 R.sup.17, R.sup.13 is hydrogen, C.sub.1 -C.sub.3 -alkyl or C.sub.3 -C.sub.4 -alkenyl, R.sup.14 is hydrogens C.sub.1 -C.sub.3 -alkyl, C.sub.1 -C.sub.3 -cyanoalkyl or C.sub.1 -C.sub.3 -alkoxy, R.sup.15 is C.sub.3 -C.sub.6 -alkinyl, C.sub.2 -C.sub.6 -alkenyl, C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.4 -halogenoalkyl, C.sub. 2 -C.sub.4 -halogenoalkenyl or C.sub.1 -C.sub.4 -alkyl, subsituted by cyano, methoxy, ethoxy, nitro, C.sub.1 -C.sub.4 -alkoxycarbonyl, methylthio, ethylthio, methylsulfonyl or ethylsulfonyl; or C.sub.3 -C.sub.4 -alkenyl substituted by nitro, cyano, methoxy or ethoxy, R.sup.16 is hydrogen, C.sub.1 -C.sub.3 -alkyl or C.sub.3 -C.sub.4 -alkenyl, R.sup.17 is hydrogen, C.sub.1 -C.sub.3 -alkyl, C.sub.1 -C.sub.3 -cyanoalkyl or C.sub.1 -C.sub.3 -alkoxy, R.sup.18 is C.sub.1 -C.sub.3 -alkyl and C.sub.1 -C.sub.3 -halogenoalkyl, W is oxygen or sulfur, Z is oxygen, sulfur, --SO-- or --SO.sub.2 -- and m is the number zero or one.

REFERENCES:
patent: 4443245 (1984-04-01), Meyer et al.
patent: 4514212 (1985-04-01), Meyer et al.
patent: 4561878 (1985-12-01), Meyer et al.
Neunhoeffer et al., Chem. Abst. 100-174740q (1984).
Meyer et al., Chem. Abst. 102-132065j (1985).
Boehner et al., Chem. Abst. 109-93074j (1988).

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