HERBICIDALLY ACTIVE SUBSTITUTED PHENYLPYRIMIDINE HYDRAZIDES
20220033363 · 2022-02-03
Inventors
- Birgit KUHN (Kelkheim, DE)
- Stefan Schnatterer (Hattersheim, DE)
- Dirk Schmutzler (Hattersheim, DE)
- Elisabeth ASMUS (Hoesbach, DE)
- Anu Bheemaiah Machettira (Frankfurt am Main, DE)
- Elmar Gatzweiler (Bad Nauheim, DE)
- Christopher Hugh Rosinger (Hofheim, GB)
Cpc classification
A01N51/00
HUMAN NECESSITIES
C07D405/12
CHEMISTRY; METALLURGY
A01N47/28
HUMAN NECESSITIES
A01N47/34
HUMAN NECESSITIES
C07D403/12
CHEMISTRY; METALLURGY
C07D401/12
CHEMISTRY; METALLURGY
C07D417/12
CHEMISTRY; METALLURGY
A01N25/32
HUMAN NECESSITIES
C07D413/12
CHEMISTRY; METALLURGY
International classification
C07D239/28
CHEMISTRY; METALLURGY
A01N25/32
HUMAN NECESSITIES
A01N47/28
HUMAN NECESSITIES
A01N47/34
HUMAN NECESSITIES
A01N51/00
HUMAN NECESSITIES
C07D401/12
CHEMISTRY; METALLURGY
C07D403/12
CHEMISTRY; METALLURGY
Abstract
The invention relates to substituted phenylpyrimidine hydrazides of the general formula (I) and their agrochemically acceptable salts
##STR00001##
and to their use in the crop protection sector.
In formula (I), the substituent R.sup.2 represents a hydrazine group. The substituents R.sup.1 and R.sup.3 to R.sup.7 represent radicals such as hydrogen, halogen, amino, nitro and alkyl.
Claims
1. A compound of formula (I) ##STR00026## And/or an agrochemically acceptable salt thereof, in which the symbols and indices have the following meanings: R.sup.1 represents (C.sub.3-C.sub.6)-cycloalkyl, (C.sub.3-C.sub.6)-cycloalkenyl or heterocyclyl, where these three aforementioned radicals are each substituted by s radicals from the group consisting of halogen, (C.sub.1-C.sub.6)-alkyl, halo-(C.sub.1-C.sub.6)-alkyl, (C.sub.2-C.sub.6)-alkenyl, halo-(C.sub.2-C.sub.6)-alkenyl, (C.sub.2-C.sub.6)-alkynyl, halo-(C.sub.3-C.sub.6)-alkynyl, (C.sub.3-C.sub.6)-cycloalkyl, halo-(C.sub.3-C.sub.6)-cycloalkyl, (C.sub.3-C.sub.6)-cycloalkenyl, halo-(C.sub.3-C.sub.6)-cycloalkenyl, (C.sub.3-C.sub.6)-cycloalkyl-(C.sub.1-C.sub.6)-alkyl, (C.sub.3-C.sub.6)-cycloalkenyl-(C.sub.1-C.sub.6)-alkyl, halo-(C.sub.3-C.sub.6)-cycloalkyl-(C.sub.1-C.sub.6)-alkyl, halo-(C.sub.3-C.sub.6)-cycloalkenyl-(C.sub.1-C.sub.6)-alkyl, R.sup.8(O)C, R.sup.8O(O)C, (R.sup.8).sub.2N(O)C, R.sup.8O, (R.sup.8).sub.2N, R.sup.9(O).sub.nS, phenyl, heteroaryl, heterocyclyl, phenyl-(C.sub.1-C.sub.6)-alkyl, heteroaryl-(C.sub.1-C.sub.6)-alkyl and heterocyclyl-(C.sub.1-C.sub.6)-alkyl, where the six latter radicals are substituted by m radicals from the group consisting of (C.sub.1-C.sub.6)-alkyl, halo-(C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-alkoxy, halo-(C.sub.1-C.sub.6)-alkoxy and halogen, and where cycloalkyl, cycloalkenyl and heterocyclyl each independently bear n oxo groups, R.sup.2 represents (R.sup.17) (R.sup.18) N(R.sup.19)N, or R.sup.2 represents R.sup.17R.sup.18C═N—(R.sup.19)N, R.sup.3, R.sup.4, R.sup.5, R.sup.6 and R.sup.7 each independently represent hydrogen, nitro, halogen, cyano, thiocyano, (C.sub.1-C.sub.6)-alkyl, halo-(C.sub.1-C.sub.6)-alkyl, (C.sub.2-C.sub.6)-alkenyl, halo-(C.sub.2-C.sub.6)-alkenyl, (C.sub.2-C.sub.6)-alkynyl, halo-(C.sub.3-C.sub.6)-alkynyl, (C.sub.3-C.sub.6)-cycloalkyl, halo-(C.sub.3-C.sub.6)-cycloalkyl, (C.sub.3-C.sub.6)-cycloalkyl-(C.sub.1-C.sub.6)-alkyl, halo-(C.sub.3-C.sub.6)-cycloalkyl-(C.sub.1-C.sub.6)-alkyl, R.sup.8(O)C, R.sup.8(R.sup.8ON═)C, R.sup.8O(O)C, (R.sup.8).sub.2N(O)C, R.sup.8(R.sup.8O)N(O)C, (R.sup.8).sub.2N(R.sup.8)N(O)C, R.sup.8(O)C(R.sup.8)N(O)C, R.sup.9O(O)C(R.sup.8)N(O)C, (R.sup.8).sub.2N(O)C(R.sup.8)N(O)C, R.sup.9(O).sub.2S(R.sup.8)N(O)C, R.sup.8O(O).sub.2S(R.sup.8)N(O)C, (R.sup.8).sub.2N(O).sub.2S(R.sup.8)N(O)C, R.sup.8O, R.sup.8(O)CO, R.sup.9(O).sub.2SO, R.sup.9O(O)CO, (R.sup.8).sub.2N(O)CO, (R.sup.8).sub.2N, R.sup.8(O)C(R.sup.8)N, R.sup.9(O).sub.2S(R.sup.8)N, R.sup.9O(O)C(R.sup.8)N, (R.sup.8).sub.2N(O)C(R.sup.8)N, R.sup.8O(O).sub.2S(R.sup.8)N, (R.sup.8).sub.2N(O).sub.2S(R.sup.8)N, R.sup.9(O).sub.nS, R.sup.8O(O).sub.2S, (R.sup.8).sub.2N(O).sub.2S, R.sup.8(O)C(R.sup.8)N(O).sub.2S, R.sup.9O(O)C(R.sup.8)N(O).sub.2S, (R.sup.8).sub.2N(O)C(R.sup.8)N(O).sub.2S, (R.sup.12O).sub.2(O)P, R.sup.8(O)C—(C.sub.1-C.sub.6)-alkyl, R.sup.8O(O)C—(C.sub.1-C.sub.6)-alkyl, (R.sup.8).sub.2N(O)C—(C.sub.1-C.sub.6)-alkyl, (R.sup.8O)(R.sup.8)N(O)C—(C.sub.1-C.sub.6)-alkyl, (R.sup.8).sub.2N(R.sup.8)N(O)C—(C.sub.1-C.sub.6)-alkyl, R.sup.8(O)C(R.sup.8)N(O)C—(C.sub.1-C.sub.6)-alkyl, R.sup.9O(O)C(R.sup.8)N(O)C—(C.sub.1-C.sub.6)-alkyl, (R.sup.8).sub.2N(O)C(R.sup.8)N(O)C—(C.sub.1-C.sub.6)-alkyl, R.sup.9(O).sub.2S(R.sup.8)N(O)C—(C.sub.1-C.sub.6)-alkyl, R.sup.8O(O).sub.2S(R.sup.8)N(O)C—(C.sub.1-C.sub.6)-alkyl, (R.sup.8).sub.2N(O).sub.2S(R.sup.8)N(O)C—(C.sub.1-C.sub.6)-alkyl, NC—(C.sub.1-C.sub.6)-alkyl, R.sup.8O—(C.sub.1-C.sub.6)-alkyl, R.sup.8(O)CO—(C.sub.1-C.sub.6)-alkyl, R.sup.9(O).sub.2SO—(C.sub.1-C.sub.6)-alkyl, R.sup.9O(O)CO—(C.sub.1-C.sub.6)-alkyl, (R.sup.8).sub.2N(O)CO—(C.sub.1-C.sub.6)-alkyl, (R.sup.8).sub.2N—(C.sub.1-C.sub.6)-alkyl, R.sup.8(O)C(R.sup.8)N—(C.sub.1-C.sub.6)-alkyl, R.sup.9(O).sub.2S(R.sup.8)N—(C.sub.1-C.sub.6)-alkyl, R.sup.9O(O)C(R.sup.8)N—(C.sub.1-C.sub.6)-alkyl, (R.sup.8).sub.2N(O)C(R.sup.8)N—(C.sub.1-C.sub.6)-alkyl, R.sup.8O(O).sub.2S(R.sup.8)N—(C.sub.1-C.sub.6)-alkyl, (R.sup.8).sub.2N(O).sub.2S(R.sup.8)N—(C.sub.1-C.sub.6)-alkyl, R.sup.9(O).sub.nS—(C.sub.1-C.sub.6)-alkyl, R.sup.8O(O).sub.2S—(C.sub.1-C.sub.6)-alkyl, (R.sup.8).sub.2N(O).sub.2S—(C.sub.1-C.sub.6)-alkyl, R.sup.8(O)C(R.sup.8)N(O).sub.2S—(C.sub.1-C.sub.6)-alkyl, R.sup.9O(O)C(R.sup.8)N(O).sub.2S—(C.sub.1-C.sub.6)-alkyl, (R.sup.8).sub.2N(O)C(R.sup.8)N(O).sub.2S—(C.sub.1-C.sub.6)-alkyl, (R.sup.12O).sub.2(O)P—(C.sub.1-C.sub.6)-alkyl, phenyl, heteroaryl, heterocyclyl, phenyl-(C.sub.1-C.sub.6)-alkyl, heteroaryl-(C.sub.1-C.sub.6)-alkyl or heterocyclyl-(C.sub.1-C.sub.6)-alkyl, where the six latter radicals are each substituted by m radicals from the group consisting of nitro, halogen, cyano, thiocyano, (C.sub.1-C.sub.6)-alkyl, halo-(C.sub.1-C.sub.6)-alkyl, (C.sub.3-C.sub.6)-cycloalkyl, R.sup.8O(O)C, (R.sup.8).sub.2N(O)C, R.sup.8O, (R.sup.8).sub.2N, R.sup.9(O).sub.nS, R.sup.8O(O).sub.2S, (R.sup.8).sub.2N(O).sub.2S and R.sup.8O—(C.sub.1-C.sub.6)-alkyl, and where cycloalkyl and heterocyclyl each independently bear n oxo groups, R.sup.8 represents hydrogen, (C.sub.1-C.sub.6)-alkyl, (C.sub.2-C.sub.6)-alkenyl, (C.sub.2-C.sub.6)-alkynyl, (C.sub.3-C.sub.6)-cycloalkyl, (C.sub.3-C.sub.6)-cycloalkenyl, (C.sub.3-C.sub.6)-cycloalkyl-(C.sub.1-C.sub.6)-alkyl, (C.sub.3-C.sub.6)-cycloalkenyl-(C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-alkyl-O—(C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-alkyl-O—(C.sub.1-C.sub.6)-alkyl-O—(C.sub.1-C.sub.6)-alkyl, (C.sub.3-C.sub.6)-cycloalkyl-(C.sub.1-C.sub.6)-alkyl-O—(C.sub.1-C.sub.6)-alkyl, (C.sub.3-C.sub.6)-cycloalkenyl-(C.sub.1-C.sub.6)-alkyl-O—(C.sub.1-C.sub.6)-alkyl or (C.sub.1-C.sub.6)-alkylthio-(C.sub.1-C.sub.6)-alkyl, where the twelve latter radicals bear s halogens, or R.sup.8 represents phenyl, phenyl-(C.sub.1-C.sub.6)-alkyl, heteroaryl, heteroaryl-(C.sub.1-C.sub.6)-alkyl, heterocyclyl, heterocyclyl-(C.sub.1-C.sub.6)-alkyl, phenyl-O—(C.sub.1-C.sub.6)-alkyl, heteroaryl-O—(C.sub.1-C.sub.6)-alkyl, heterocyclyl-O—(C.sub.1-C.sub.6)-alkyl, phenyl-N(R.sup.10)—(C.sub.1-C.sub.6)-alkyl, heteroaryl-N(R.sup.10)—(C.sub.1-C.sub.6)-alkyl, heterocyclyl-N(R.sup.10)—(C.sub.1-C.sub.6)-alkyl, phenyl-S(O).sub.n—(C.sub.1-C.sub.6)-alkyl, heteroaryl-S(O).sub.n—(C.sub.1-C.sub.6)-alkyl or heterocyclyl-S(O).sub.n—(C.sub.1-C.sub.6)-alkyl, where the radicals are each substituted by m radicals from the group consisting of nitro, halogen, cyano, thiocyano, (C.sub.1-C.sub.6)-alkyl, halo-(C.sub.1-C.sub.6)-alkyl, (C.sub.3-C.sub.6)-cycloalkyl, (C.sub.3-C.sub.6)-cycloalkenyl, R.sup.10O(O)C, (R.sup.10).sub.2N(O)C, R.sup.10O, (R.sup.10).sub.2N, R.sup.11(O).sub.nS, R.sup.10O(O).sub.2S, (R.sup.10).sub.2N(O).sub.2S and R.sup.10O—(C.sub.1-C.sub.6)-alkyl, and where (C.sub.3-C.sub.6)-cycloalkyl, (C.sub.3-C.sub.6)-cycloalkenyl and heterocyclyl each independently bear n oxo groups, or the R.sup.8 radicals form a ring with the heteroatom or with the heteroatoms via which they are bonded, specifically a heterocyclyl, heterocyclenyl, heteroaryl, arylheterocyclyl, arylheterocyclenyl, heteroarylheterocyclyl, heteroarylheterocyclenyl, heterocyclylheteroaryl or heterocyclenylheteroaryl, where each of these rings in turn is substituted by m radicals from the group consisting of nitro, halogen, cyano, thiocyano, (C.sub.1-C.sub.6)-alkyl, halo-(C.sub.1-C.sub.6)-alkyl, (C.sub.3-C.sub.6)-cycloalkyl, (C.sub.3-C.sub.6)-cycloalkenyl, R.sup.10O(O)C, (R.sup.10).sub.2N(O)C, R.sup.10O, (R.sup.10).sub.2N, R.sup.11(O).sub.nS, R.sup.10O(O).sub.2S, (R.sup.10).sub.2N(O).sub.2S and R.sup.10O—(C.sub.1-C.sub.6)-alkyl and oxo, R.sup.9 represents (C.sub.1-C.sub.6)-alkyl, (C.sub.2-C.sub.6)-alkenyl, (C.sub.2-C.sub.6)-alkynyl, (C.sub.3-C.sub.6)-cycloalkyl, (C.sub.3-C.sub.6)-cycloalkenyl, (C.sub.3-C.sub.6)-cycloalkyl-(C.sub.1-C.sub.6)-alkyl, (C.sub.3-C.sub.6)-cycloalkenyl-(C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-alkyl-O—(C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-alkyl-O—(C.sub.1-C.sub.6)-alkyl-O—(C.sub.1-C.sub.6)-alkyl, (C.sub.3-C.sub.6)-cycloalkyl-(C.sub.1-C.sub.6)-alkyl-O—(C.sub.1-C.sub.6)-alkyl, (C.sub.3-C.sub.6)-cycloalkenyl-(C.sub.1-C.sub.6)-alkyl-O—(C.sub.1-C.sub.6)-alkyl or (C.sub.1-C.sub.6)-alkylthio-(C.sub.1-C.sub.6)-alkyl, where the radicals bear s halogens, or R.sup.9 represents phenyl, phenyl-(C.sub.1-C.sub.6)-alkyl, heteroaryl, heteroaryl-(C.sub.1-C.sub.6)-alkyl, heterocyclyl, heterocyclyl-(C.sub.1-C.sub.6)-alkyl, phenyl-O—(C.sub.1-C.sub.6)-alkyl, heteroaryl-O—(C.sub.1-C.sub.6)-alkyl, heterocyclyl-O—(C.sub.1-C.sub.6)-alkyl, phenyl-N(R.sup.10)—(C.sub.1-C.sub.6)-alkyl, heteroaryl-N(R.sup.10)—(C.sub.1-C.sub.6)-alkyl, heterocyclyl-N(R.sup.10)—(C.sub.1-C.sub.6)-alkyl, phenyl-S(O).sub.n—(C.sub.1-C.sub.6)-alkyl, heteroaryl-S(O).sub.n—(C.sub.1-C.sub.6)-alkyl or heterocyclyl-S(O).sub.n—(C.sub.1-C.sub.6)-alkyl, where the radicals are each substituted by m radicals from the group consisting of nitro, halogen, cyano, thiocyano, (C.sub.1-C.sub.6)-alkyl, halo-(C.sub.1-C.sub.6)-alkyl, (C.sub.3-C.sub.6)-cycloalkyl, (C.sub.3-C.sub.6)-cycloalkenyl, R.sup.10O(O)C, (R.sup.10).sub.2N(O)C, R.sup.10O, (R.sup.10).sub.2N, R.sup.11(O).sub.nS, R.sup.10O(O).sub.2S, (R.sup.10).sub.2N(O).sub.2S and R.sup.10O—(C.sub.1-C.sub.6)-alkyl, and where (C.sub.3-C.sub.6)-cycloalkyl, (C.sub.3-C.sub.6)-cycloalkenyl and heterocyclyl each independently bear n oxo groups, R.sup.10 represents hydrogen, (C.sub.1-C.sub.6)-alkyl, halo-(C.sub.1-C.sub.6)-alkyl, (C.sub.2-C.sub.6)-alkenyl, (C.sub.2-C.sub.6)-alkynyl, (C.sub.3-C.sub.6)-cycloalkyl, (C.sub.3-C.sub.6)-cycloalkyl-(C.sub.1-C.sub.6)-alkyl or phenyl, R.sup.11 represents (C.sub.1-C.sub.6)-alkyl, halo-(C.sub.1-C.sub.6)-alkyl, (C.sub.2-C.sub.6)-alkenyl, (C.sub.2-C.sub.6)-alkynyl, (C.sub.3-C.sub.6)-cycloalkyl, (C.sub.3-C.sub.6)-cycloalkyl-(C.sub.1-C.sub.6)-alkyl or phenyl, R.sup.12 represents hydrogen or (C.sub.1-C.sub.4)-alkyl, R.sup.13 represents hydrogen, (C.sub.1-C.sub.6)-alkyl, (C.sub.2-C.sub.6)-alkenyl, (C.sub.2-C.sub.6)-alkynyl, (C.sub.3-C.sub.6)-cycloalkyl, (C.sub.3-C.sub.6)-cycloalkenyl, (C.sub.3-C.sub.6)-cycloalkyl-(C.sub.1-C.sub.6)-alkyl, (C.sub.3-C.sub.6)-cycloalkenyl-(C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-alkyl-O—(C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-alkyl-O—(C.sub.1-C.sub.6)-alkyl-O—(C.sub.1-C.sub.6)-alkyl, (C.sub.3-C.sub.6)-cycloalkyl-(C.sub.1-C.sub.6)-alkyl-O—(C.sub.1-C.sub.6)-alkyl, (C.sub.3-C.sub.6)-cycloalkenyl-(C.sub.1-C.sub.6)-alkyl-O—(C.sub.1-C.sub.6)-alkyl or (C.sub.1-C.sub.6)-alkylthio-(C.sub.1-C.sub.6)-alkyl, where the twelve latter radicals are substituted by s radicals from the group consisting of nitro, halogen, cyano, thiocyano, (C.sub.1-C.sub.6)-alkyl, halo-(C.sub.1-C.sub.6)-alkyl, (C.sub.3-C.sub.6)-cycloalkyl, (C.sub.3-C.sub.6)-cycloalkenyl, R.sup.10O(O)C, (R.sup.10).sub.2N(O)C, R.sup.10O, (R.sup.10).sub.2N, R.sup.11(O).sub.nS, R.sup.10O(O).sub.2S, (R.sup.10).sub.2N(O).sub.2S and R.sup.10O—(C.sub.1-C.sub.6)-alkyl and oxo, or R.sup.13 represents phenyl, phenyl-(C.sub.1-C.sub.6)-alkyl, heteroaryl, heteroaryl-(C.sub.1-C.sub.6)-alkyl, heterocyclyl, heterocyclyl-(C.sub.1-C.sub.6)-alkyl, phenyl-O—(C.sub.1-C.sub.6)-alkyl, heteroaryl-O—(C.sub.1-C.sub.6)-alkyl, heterocyclyl-O—(C.sub.1-C.sub.6)-alkyl, phenyl-N(R.sup.10)—(C.sub.1-C.sub.6)-alkyl, heteroaryl-N(R.sup.10)—(C.sub.1-C.sub.6)-alkyl, heterocyclyl-N(R.sup.10)—(C.sub.1-C.sub.6)-alkyl, phenyl-S(O).sub.n—(C.sub.1-C.sub.6)-alkyl, heteroaryl-S(O).sub.n—(C.sub.1-C.sub.6)-alkyl or heterocyclyl-S(O).sub.n—(C.sub.1-C.sub.6)-alkyl, where the radicals are each substituted by m radicals from the group consisting of nitro, halogen, cyano, thiocyano, (C.sub.1-C.sub.6)-alkyl, halo-(C.sub.1-C.sub.6)-alkyl, (C.sub.3-C.sub.6)-cycloalkyl, (C.sub.3-C.sub.6)-cycloalkenyl, R.sup.10O(O)C, (R.sup.10).sub.2N(O)C, R.sup.10O, (R.sup.10).sub.2N, R.sup.11(O).sub.nS, R.sup.10O(O).sub.2S, (R.sup.10).sub.2N(O).sub.2S and R.sup.10O—(C.sub.1-C.sub.6)-alkyl, and where (C.sub.3-C.sub.6)-cycloalkyl, (C.sub.3-C.sub.6)-cycloalkenyl and heterocyclyl each independently bear n oxo groups, R.sup.14 represents (C.sub.1-C.sub.6)-alkyl, (C.sub.2-C.sub.6)-alkenyl, (C.sub.2-C.sub.6)-alkynyl, (C.sub.3-C.sub.6)-cycloalkyl, (C.sub.3-C.sub.6)-cycloalkenyl, (C.sub.3-C.sub.6)-cycloalkyl-(C.sub.1-C.sub.6)-alkyl, (C.sub.3-C.sub.6)-cycloalkenyl-(C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-alkyl-O—(C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-alkyl-O—(C.sub.1-C.sub.6)-alkyl-O—(C.sub.1-C.sub.6)-alkyl, (C.sub.3-C.sub.6)-cycloalkyl-(C.sub.1-C.sub.6)-alkyl-O—(C.sub.1-C.sub.6)-alkyl, (C.sub.3-C.sub.6)-cycloalkenyl-(C.sub.1-C.sub.6)-alkyl-O—(C.sub.1-C.sub.6)-alkyl or (C.sub.1-C.sub.6)-alkylthio-(C.sub.1-C.sub.6)-alkyl, where the 12 latter radicals are substituted by s radicals from the group consisting of nitro, halogen, cyano, thiocyano, (C.sub.1-C.sub.6)-alkyl, halo-(C.sub.1-C.sub.6)-alkyl, (C.sub.3-C.sub.6)-cycloalkyl, (C.sub.3-C.sub.6)-cycloalkenyl, R.sup.10O(O)C, (R.sup.10).sub.2N(O)C, R.sup.10O, (R.sup.10).sub.2N, R.sup.11(O).sub.nS, R.sup.10O(O).sub.2S, (R.sup.10).sub.2N(O).sub.2S and R.sup.10O—(C.sub.1-C.sub.6)-alkyl and oxo, or R.sup.14 represents phenyl, phenyl-(C.sub.1-C.sub.6)-alkyl, heteroaryl, heteroaryl-(C.sub.1-C.sub.6)-alkyl, heterocyclyl, heterocyclyl-(C.sub.1-C.sub.6)-alkyl, phenyl-O—(C.sub.1-C.sub.6)-alkyl, heteroaryl-O—(C.sub.1-C.sub.6)-alkyl, heterocyclyl-O—(C.sub.1-C.sub.6)-alkyl, phenyl-N(R.sup.10)—(C.sub.1-C.sub.6)-alkyl, heteroaryl-N(R.sup.10)—(C.sub.1-C.sub.6)-alkyl, heterocyclyl-N(R.sup.10)—(C.sub.1-C.sub.6)-alkyl, phenyl-S(O).sub.n—(C.sub.1-C.sub.6)-alkyl, heteroaryl-S(O).sub.n—(C.sub.1-C.sub.6)-alkyl or heterocyclyl-S(O).sub.n—(C.sub.1-C.sub.6)-alkyl, where the radicals are each substituted by m radicals from the group consisting of nitro, halogen, cyano, thiocyano, (C.sub.1-C.sub.6)-alkyl, halo-(C.sub.1-C.sub.6)-alkyl, (C.sub.3-C.sub.6)-cycloalkyl, (C.sub.3-C.sub.6)-cycloalkenyl, R.sup.10O(O)C, (R.sup.10).sub.2N(O)C, R.sup.10O, (R.sup.10).sub.2N, R.sup.11(O).sub.nS, R.sup.10O(O).sub.2S, (R.sup.10).sub.2N(O).sub.2S and R.sup.10O—(C.sub.1-C.sub.6)-alkyl, and where (C.sub.3-C.sub.6)-cycloalkyl, (C.sub.3-C.sub.6)-cycloalkenyl and heterocyclyl each independently bear n oxo groups, R.sup.17 and R.sup.18 and R.sup.19 independently represent R.sup.13 or R.sup.14S(O).sub.2, (R.sup.13).sub.2NS(O).sub.2, R.sup.13OS(O).sub.2, R.sup.13C(O), (R.sup.13).sub.2NC(O), (R.sup.13).sub.2NC(S), R.sup.13OC(O), R.sup.13OC(O)C(O), (R.sup.13).sub.2NC(O)C(O), or the (R.sup.17 and R.sup.18) or (R.sup.17 and R.sup.19) radicals form a ring with the carbon atom, or with the heteroatom or with the heteroatoms via which they are bonded, specifically a cycloalkyl, cycloalkenyl, heterocyclyl, heterocyclenyl, heteroaryl, arylheterocyclyl, arylheterocyclenyl, heteroarylheterocyclyl, heteroarylheterocyclenyl, heterocyclylheteroaryl or heterocyclenylheteroaryl, where each of these rings in turn is substituted by m radicals from the group consisting of nitro, halogen, cyano, thiocyano, (C.sub.1-C.sub.6)-alkyl, halo-(C.sub.1-C.sub.6)-alkyl, (C.sub.3-C.sub.6)-cycloalkyl, (C.sub.3-C.sub.6)-cycloalkenyl, R.sup.10O(O)C, (R.sup.10).sub.2N(O)C, R.sup.10O, (R.sup.10).sub.2N, R.sup.11(O).sub.nS, R.sup.10O(O).sub.2S, (R.sup.10).sub.2N(O).sub.2S and R.sup.10O—(C.sub.1-C.sub.6)-alkyl and oxo, m represents 0, 1, 2, 3, 4 or 5, n represents 0, 1 or 2, s represents 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10 or 11.
2. The compound of formula (I) and/or salt as claimed in claim 1, in which R.sup.1 represents (C.sub.3-C.sub.6)-cycloalkyl, (C.sub.3-C.sub.6)-cycloalkenyl or heterocyclyl, where these three radicals are each substituted by s radicals from the group consisting of halogen, (C.sub.1-C.sub.6)-alkyl and halo-(C.sub.1-C.sub.6)-alkyl and where cycloalkyl, cycloalkenyl and heterocyclyl each independently bear n oxo groups, R.sup.2 represents (R.sup.17) (R.sup.18) N(R.sup.19)N, or R.sup.2 represents R.sup.17R.sup.18C═N—(R.sup.19)N, R.sup.3, R.sup.4, R.sup.5, R.sup.6 and R.sup.7 each independently represent hydrogen, nitro, halogen, cyano, (C.sub.1-C.sub.6)-alkyl, halo-(C.sub.1-C.sub.6)-alkyl, (C.sub.2-C.sub.6)-alkenyl, (C.sub.2-C.sub.6)-alkynyl, (C.sub.3-C.sub.6)-cycloalkyl, halo-(C.sub.3-C.sub.6)-cycloalkyl, (C.sub.3-C.sub.6)-cycloalkyl-(C.sub.1-C.sub.6)-alkyl, halo-(C.sub.3-C.sub.6)-cycloalkyl-(C.sub.1-C.sub.6)-alkyl, R.sup.8(O)C, R.sup.8(R.sup.8ON═)C, R.sup.8O(O)C, (R.sup.8).sub.2N(O)C, R.sup.8O, (R.sup.8).sub.2N, R.sup.8(O)C(R.sup.8)N, R.sup.9(O).sub.2S(R.sup.8)N, R.sup.9O(O)C(R.sup.8)N, (R.sup.8).sub.2N(O)C(R.sup.8)N, R.sup.9(O).sub.nS, R.sup.8O(O).sub.2S, (R.sup.8).sub.2N(O).sub.2S, (R.sup.12O).sub.2(O)P, R.sup.8(O)C—(C.sub.1-C.sub.6)-alkyl, R.sup.8O(O)C—(C.sub.1-C.sub.6)-alkyl, (R.sup.8).sub.2N(O)C—(C.sub.1-C.sub.6)-alkyl, NC—(C.sub.1-C.sub.6)-alkyl, R.sup.8O—(C.sub.1-C.sub.6)-alkyl, (R.sup.8).sub.2N—(C.sub.1-C.sub.6)-alkyl, R.sup.8(O)C(R.sup.8)N—(C.sub.1-C.sub.6)-alkyl, R.sup.9(O).sub.2S(R.sup.8)N—(C.sub.1-C.sub.6)-alkyl, R.sup.9O(O)C(R.sup.8)N—(C.sub.1-C.sub.6)-alkyl, (R.sup.8).sub.2N(O)C(R.sup.8)N—(C.sub.1-C.sub.6)-alkyl, R.sup.9(O).sub.nS—(C.sub.1-C.sub.6)-alkyl, R.sup.8O(O).sub.2S—(C.sub.1-C.sub.6)-alkyl, (R.sup.8).sub.2N(O).sub.2S—(C.sub.1-C.sub.6)-alkyl, (R.sup.12O).sub.2(O)P—(C.sub.1-C.sub.6)-alkyl, phenyl, heteroaryl, heterocyclyl, phenyl-(C.sub.1-C.sub.6)-alkyl, heteroaryl-(C.sub.1-C.sub.6)-alkyl, heterocyclyl-(C.sub.1-C.sub.6)-alkyl, where the six latter radicals are each substituted by m radicals from the group consisting of nitro, halogen, cyano, (C.sub.1-C.sub.6)-alkyl, halo-(C.sub.1-C.sub.6)-alkyl, R.sup.8O, (R.sup.8).sub.2N, R.sup.9(O).sub.nS, R.sup.8O(O).sub.2S, (R.sup.8).sub.2N(O).sub.2S and R.sup.8O—(C.sub.1-C.sub.6)-alkyl, and where heterocyclyl bears n oxo groups, R.sup.8 represents hydrogen, (C.sub.1-C.sub.6)-alkyl, (C.sub.2-C.sub.6)-alkenyl, (C.sub.2-C.sub.6)-alkynyl, (C.sub.3-C.sub.6)-cycloalkyl, (C.sub.3-C.sub.6)-cycloalkenyl, (C.sub.3-C.sub.6)-cycloalkyl-(C.sub.1-C.sub.6)-alkyl, (C.sub.3-C.sub.6)-cycloalkenyl-(C.sub.1-C.sub.6)-alkyl, where the seven latter radicals bear s halogens, or R.sup.8 represents phenyl, phenyl-(C.sub.1-C.sub.6)-alkyl, heteroaryl, heteroaryl-(C.sub.1-C.sub.6)-alkyl, heterocyclyl, heterocyclyl-(C.sub.1-C.sub.6)-alkyl, phenyl-O—(C.sub.1-C.sub.6)-alkyl, heteroaryl-O—(C.sub.1-C.sub.6)-alkyl, heterocyclyl-O—(C.sub.1-C.sub.6)-alkyl, phenyl-N(R.sup.10)—(C.sub.1-C.sub.6)-alkyl, heteroaryl-N(R.sup.10)—(C.sub.1-C.sub.6)-alkyl, heterocyclyl-N(R.sup.10)—(C.sub.1-C.sub.6)-alkyl, phenyl-S(O).sub.n—(C.sub.1-C.sub.6)-alkyl, heteroaryl-S(O).sub.n—(C.sub.1-C.sub.6)-alkyl or heterocyclyl-S(O).sub.n—(C.sub.1-C.sub.6)-alkyl, where the radicals are each substituted by m radicals from the group consisting of nitro, halogen, cyano, (C.sub.1-C.sub.6)-alkyl, halo-(C.sub.1-C.sub.6)-alkyl, (C.sub.3-C.sub.6)-cycloalkyl, (C.sub.3-C.sub.6)-cycloalkenyl, R.sup.10O(O)C, (R.sup.10).sub.2N(O)C, R.sup.10O, (R.sup.10).sub.2N, R.sup.11(O).sub.nS, R.sup.10O(O).sub.2S, (R.sup.10).sub.2N(O).sub.2S and R.sup.10O—(C.sub.1-C.sub.6)-alkyl, and where (C.sub.3-C.sub.6)-cycloalkyl, (C.sub.3-C.sub.6)-cycloalkenyl and heterocyclyl each independently bear n oxo groups, or the R.sup.8 radicals form a ring with the heteroatom or with the heteroatoms via which they are bonded, specifically a heterocyclyl, heterocyclenyl, heteroaryl, arylheterocyclyl, arylheterocyclenyl, heteroarylheterocyclyl, heteroarylheterocyclenyl, heterocyclylheteroaryl or heterocyclenylheteroaryl, where each of these rings in turn is substituted by m radicals from the group consisting of nitro, halogen, cyano, thiocyano, (C.sub.1-C.sub.6)-alkyl, halo-(C.sub.1-C.sub.6)-alkyl, (C.sub.3-C.sub.6)-cycloalkyl, (C.sub.3-C.sub.6)-cycloalkenyl, R.sup.10O(O)C, (R.sup.10).sub.2N(O)C, R.sup.10O, (R.sup.10).sub.2N, R.sup.11(O).sub.nS, R.sup.10O(O).sub.2S, (R.sup.10).sub.2N(O).sub.2S and R.sup.10O—(C.sub.1-C.sub.6)-alkyl and oxo, R.sup.9 represents (C.sub.1-C.sub.6)-alkyl, (C.sub.3-C.sub.6)-cycloalkyl-(C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-alkyl-O—(C.sub.1-C.sub.6)-alkyl, (C.sub.3-C.sub.6)-cycloalkyl-(C.sub.1-C.sub.6)-alkyl-O—(C.sub.1-C.sub.6)-alkyl, phenyl, phenyl-(C.sub.1-C.sub.6)-alkyl, heteroaryl, heteroaryl-(C.sub.1-C.sub.6)-alkyl, heterocyclyl, heterocyclyl-(C.sub.1-C.sub.6)-alkyl, phenyl-O—(C.sub.1-C.sub.6)-alkyl, heteroaryl-O—(C.sub.1-C.sub.6)-alkyl or heterocyclyl-O—(C.sub.1-C.sub.6)-alkyl, where the nine latter radicals are each substituted by m radicals from the group consisting of nitro, halogen, (C.sub.1-C.sub.6)-alkyl, halo-(C.sub.1-C.sub.6)-alkyl, R.sup.10O(O)C, (R.sup.10).sub.2N(O)C, R.sup.10O, (R.sup.10).sub.2N, R.sup.11(O).sub.nS and R.sup.10O—(C.sub.1-C.sub.6)-alkyl, and where heterocyclyl bears n oxo groups, R.sup.10 represents hydrogen or (C.sub.1-C.sub.6)-alkyl, R.sup.11 represents (C.sub.1-C.sub.6)-alkyl, R.sup.12 represents (C.sub.1-C.sub.4)-alkyl, R.sup.13 represents hydrogen, (C.sub.1-C.sub.6)-alkyl, (C.sub.2-C.sub.6)-alkenyl, (C.sub.2-C.sub.6)-alkynyl, (C.sub.3-C.sub.6)-cycloalkyl, (C.sub.3-C.sub.6)-cycloalkenyl, (C.sub.3-C.sub.6)-cycloalkyl-(C.sub.1-C.sub.6)-alkyl, (C.sub.3-C.sub.6)-cycloalkenyl-(C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-alkyl-O—(C.sub.1-C.sub.6)-alkyl, where the eight latter radicals are substituted by s radicals from the group consisting of nitro, halogen, cyano, (C.sub.1-C.sub.6)-alkyl, halo-(C.sub.1-C.sub.6)-alkyl, (C.sub.3-C.sub.6)-cycloalkyl, (C.sub.3-C.sub.6)-cycloalkenyl, R.sup.10O(O)C, (R.sup.10).sub.2N(O)C, R.sup.10O, (R.sup.10).sub.2N, R.sup.11(O).sub.nS, R.sup.10O(O).sub.2S, (R.sup.10).sub.2N(O).sub.2S and R.sup.10O—(C.sub.1-C.sub.6)-alkyl and oxo, or R.sup.13 represents phenyl, phenyl-(C.sub.1-C.sub.6)-alkyl, heteroaryl, heteroaryl-(C.sub.1-C.sub.6)-alkyl, heterocyclyl, heterocyclyl-(C.sub.1-C.sub.6)-alkyl, phenyl-O—(C.sub.1-C.sub.6)-alkyl, heteroaryl-O—(C.sub.1-C.sub.6)-alkyl, heterocyclyl-O—(C.sub.1-C.sub.6)-alkyl, phenyl-N(R.sup.10)—(C.sub.1-C.sub.6)-alkyl, heteroaryl-N(R.sup.10)—(C.sub.1-C.sub.6)-alkyl, heterocyclyl-N(R.sup.10)—(C.sub.1-C.sub.6)-alkyl, phenyl-S(O).sub.n—(C.sub.1-C.sub.6)-alkyl, heteroaryl-S(O).sub.n—(C.sub.1-C.sub.6)-alkyl or heterocyclyl-S(O).sub.n—(C.sub.1-C.sub.6)-alkyl, where the radicals are each substituted by m radicals from the group consisting of nitro, halogen, cyano, (C.sub.1-C.sub.6)-alkyl, halo-(C.sub.1-C.sub.6)-alkyl, (C.sub.3-C.sub.6)-cycloalkyl, (C.sub.3-C.sub.6)-cycloalkenyl, R.sup.10O(O)C, (R.sup.10).sub.2N(O)C, R.sup.10O, (R.sup.10).sub.2N, R.sup.11(O).sub.nS, R.sup.10O(O).sub.2S, (R.sup.10).sub.2N(O).sub.2S and R.sup.10O—(C.sub.1-C.sub.6)-alkyl, and where (C.sub.3-C.sub.6)-cycloalkyl, (C.sub.3-C.sub.6)-cycloalkenyl and heterocyclyl each independently bear n oxo groups, R.sup.14 represents (C.sub.1-C.sub.6)-alkyl, (C.sub.2-C.sub.6)-alkenyl, (C.sub.2-C.sub.6)-alkynyl, (C.sub.3-C.sub.6)-cycloalkyl, (C.sub.3-C.sub.6)-cycloalkenyl, (C.sub.3-C.sub.6)-cycloalkyl-(C.sub.1-C.sub.6)-alkyl, (C.sub.3-C.sub.6)-cycloalkenyl-(C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-alkyl-O—(C.sub.1-C.sub.6)-alkyl, where the eight latter radicals are substituted by s radicals from the group consisting of nitro, halogen, cyano, (C.sub.1-C.sub.6)-alkyl, halo-(C.sub.1-C.sub.6)-alkyl, (C.sub.3-C.sub.6)-cycloalkyl, (C.sub.3-C.sub.6)-cycloalkenyl, R.sup.10O(O)C, (R.sup.10).sub.2N(O)C, R.sup.10O, (R.sup.10).sub.2N, R.sup.11(O).sub.nS, R.sup.10O(O).sub.2S, (R.sup.10).sub.2N(O).sub.2S and R.sup.10O—(C.sub.1-C.sub.6)-alkyl and oxo, or R.sup.14 represents phenyl, phenyl-(C.sub.1-C.sub.6)-alkyl, heteroaryl, heteroaryl-(C.sub.1-C.sub.6)-alkyl, heterocyclyl, heterocyclyl-(C.sub.1-C.sub.6)-alkyl, phenyl-O—(C.sub.1-C.sub.6)-alkyl, heteroaryl-O—(C.sub.1-C.sub.6)-alkyl, heterocyclyl-O—(C.sub.1-C.sub.6)-alkyl, phenyl-N(R.sup.10)—(C.sub.1-C.sub.6)-alkyl, heteroaryl-N(R.sup.10)—(C.sub.1-C.sub.6)-alkyl, heterocyclyl-N(R.sup.10)—(C.sub.1-C.sub.6)-alkyl, phenyl-S(O).sub.n—(C.sub.1-C.sub.6)-alkyl, heteroaryl-S(O).sub.n—(C.sub.1-C.sub.6)-alkyl or heterocyclyl-S(O).sub.n—(C.sub.1-C.sub.6)-alkyl, where the radicals are each substituted by m radicals from the group consisting of nitro, halogen, cyano, (C.sub.1-C.sub.6)-alkyl, halo-(C.sub.1-C.sub.6)-alkyl, (C.sub.3-C.sub.6)-cycloalkyl, (C.sub.3-C.sub.6)-cycloalkenyl, R.sup.10O(O)C, (R.sup.10).sub.2N(O)C, R.sup.10O, (R.sup.10).sub.2N, R.sup.11(O).sub.nS, R.sup.10O(O).sub.2S, (R.sup.10).sub.2N(O).sub.2S and R.sup.10O—(C.sub.1-C.sub.6)-alkyl, and where (C.sub.3-C.sub.6)-cycloalkyl, (C.sub.3-C.sub.6)-cycloalkenyl and heterocyclyl each independently bear n oxo groups, R.sup.17, R.sup.18 and R.sup.19 independently represent R.sup.13 or R.sup.14S(O).sub.2, (R.sup.13).sub.2NS(O).sub.2, R.sup.13O S(O).sub.2, R.sup.13C(O), (R.sup.13).sub.2NC(O), (R.sup.13).sub.2NC(S), R.sup.13OC(O), R.sup.13OC(O)C(O), (R.sup.13).sub.2NC(O)C(O) or the (R.sup.17 and R.sup.18) or (R.sup.17 and R.sup.19) radicals form a ring with the carbon atom, or with the heteroatom or with the heteroatoms via which they are bonded, specifically a cycloalkyl, cycloalkenyl, heterocyclyl, heterocyclenyl, heteroaryl, arylheterocyclyl, arylheterocyclenyl, heteroarylheterocyclyl, heteroarylheterocyclenyl, heterocyclylheteroaryl or heterocyclenylheteroaryl, where each of these rings in turn is substituted by m radicals from the group consisting of nitro, halogen, cyano, (C.sub.1-C.sub.6)-alkyl, halo-(C.sub.1-C.sub.6)-alkyl, (C.sub.3-C.sub.6)-cycloalkyl, (C.sub.3-C.sub.6)-cycloalkenyl, R.sup.10O(O)C, (R.sup.10).sub.2N(O)C, R.sup.10O, (R.sup.10).sub.2N, R.sup.11(O).sub.nS, R.sup.10O(O).sub.2S, (R.sup.10).sub.2N(O).sub.2S and R.sup.10O—(C.sub.1-C.sub.6)-alkyl and oxo, m represents 0 or 1, 2, 3, 4 or 5, n represents 0, 1 or 2, s represents 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10 or 11.
3. The compound of formula (I) and/or salt as claimed in claim 1, in which R.sup.1 represents (C.sub.3-C.sub.6)-cycloalkyl, where this cycloalkyl group is substituted by s radicals from the group consisting of halogen, (C.sub.1-C.sub.6)-alkyl and halo-(C.sub.1-C.sub.6)-alkyl, R.sup.2 represents (R.sup.17) (R.sup.18) N(R.sup.19)N or R.sup.17R.sup.18C═N—(R.sup.19)N, R.sup.3, R.sup.4, R.sup.5, R.sup.6 and R.sup.7 each independently represent hydrogen, nitro, halogen, cyano, (C.sub.1-C.sub.6)-alkyl, halo-(C.sub.1-C.sub.6)-alkyl, (C.sub.3-C.sub.6)-cycloalkyl, R.sup.8O(O)C, R.sup.8O or R.sup.9(O).sub.nS, R.sup.8 represents hydrogen, (C.sub.1-C.sub.6)-alkyl, (C.sub.2-C.sub.6)-alkenyl, (C.sub.2-C.sub.6)-alkynyl, (C.sub.3-C.sub.6)-cycloalkyl, (C.sub.3-C.sub.6)-cycloalkenyl, (C.sub.3-C.sub.6)-cycloalkyl-(C.sub.1-C.sub.6)-alkyl, (C.sub.3-C.sub.6)-cycloalkenyl-(C.sub.1-C.sub.6)-alkyl, where the seven latter radicals bear s halogens, or R.sup.8 represents phenyl, phenyl-(C.sub.1-C.sub.6)-alkyl, heteroaryl, heteroaryl-(C.sub.1-C.sub.6)-alkyl, heterocyclyl, heterocyclyl-(C.sub.1-C.sub.6)-alkyl, phenyl-O—(C.sub.1-C.sub.6)-alkyl, heteroaryl-O—(C.sub.1-C.sub.6)-alkyl, heterocyclyl-O—(C.sub.1-C.sub.6)-alkyl, phenyl-N(R.sup.10)—(C.sub.1-C.sub.6)-alkyl, heteroaryl-N(R.sup.10)—(C.sub.1-C.sub.6)-alkyl, heterocyclyl-N(R.sup.10)—(C.sub.1-C.sub.6)-alkyl, phenyl-S(O).sub.n—(C.sub.1-C.sub.6)-alkyl, heteroaryl-S(O).sub.n—(C.sub.1-C.sub.6)-alkyl or heterocyclyl-S(O).sub.n—(C.sub.1-C.sub.6)-alkyl, where the radicals are each substituted by m radicals from the group consisting of nitro, halogen, cyano, (C.sub.1-C.sub.6)-alkyl, halo-(C.sub.1-C.sub.6)-alkyl, (C.sub.3-C.sub.6)-cycloalkyl, (C.sub.3-C.sub.6)-cycloalkenyl, R.sup.10O(O)C, (R.sup.10).sub.2N(O)C, R.sup.10O, (R.sup.10).sub.2N, R.sup.11(O).sub.nS, R.sup.10O(O).sub.2S, (R.sup.10).sub.2N(O).sub.2S and R.sup.10O—(C.sub.1-C.sub.6)-alkyl, and where (C.sub.3-C.sub.6)-cycloalkyl, (C.sub.3-C.sub.6)-cycloalkenyl and heterocyclyl each independently bear n oxo groups, or the R.sup.8 radicals form a ring with the heteroatom or with the heteroatoms via which they are bonded, specifically a heterocyclyl, heterocyclenyl, heteroaryl, arylheterocyclyl, arylheterocyclenyl, heteroarylheterocyclyl, heteroarylheterocyclenyl, heterocyclylheteroaryl or heterocyclenylheteroaryl, where each of these rings in turn is substituted by m radicals from the group consisting of nitro, halogen, cyano, (C.sub.1-C.sub.6)-alkyl, halo-(C.sub.1-C.sub.6)-alkyl, (C.sub.3-C.sub.6)-cycloalkyl, (C.sub.3-C.sub.6)-cycloalkenyl, R.sup.10O(O)C, (R.sup.10).sub.2N(O)C, R.sup.10O, (R.sup.10).sub.2N, R.sup.11(O).sub.nS, R.sup.10O(O).sub.2S, (R.sup.10).sub.2N(O).sub.2S and R.sup.10O—(C.sub.1-C.sub.6)-alkyl and oxo, R.sup.9 represents (C.sub.1-C.sub.6)-alkyl, (C.sub.3-C.sub.6)-cycloalkyl-(C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-alkyl-O—(C.sub.1-C.sub.6)-alkyl, (C.sub.3-C.sub.6)-cycloalkyl-(C.sub.1-C.sub.6)-alkyl-O—(C.sub.1-C.sub.6)-alkyl, phenyl, phenyl-(C.sub.1-C.sub.6)-alkyl, heteroaryl, heteroaryl-(C.sub.1-C.sub.6)-alkyl, heterocyclyl, heterocyclyl-(C.sub.1-C.sub.6)-alkyl, phenyl-O—(C.sub.1-C.sub.6)-alkyl, heteroaryl-O—(C.sub.1-C.sub.6)-alkyl or heterocyclyl-O—(C.sub.1-C.sub.6)-alkyl, where the nine latter radicals are each substituted by m radicals from the group consisting of nitro, halogen, (C.sub.1-C.sub.6)-alkyl, halo-(C.sub.1-C.sub.6)-alkyl, R.sup.10O(O)C, (R.sup.10).sub.2N(O)C, R.sup.10O, (R.sup.10).sub.2N, R.sup.11(O).sub.nS and R.sup.10O—(C.sub.1-C.sub.6)-alkyl, and where heterocyclyl bears n oxo groups, R.sup.10 represents hydrogen or (C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-haloalkyl R.sup.11 represents (C.sub.1-C.sub.6)-alkyl, R.sup.12 represents (C.sub.1-C.sub.4)-alkyl, R.sup.13 represents hydrogen, (C.sub.1-C.sub.6)-alkyl, (C.sub.2-C.sub.6)-alkenyl, (C.sub.2-C.sub.6)-alkynyl, (C.sub.3-C.sub.6)-cycloalkyl, (C.sub.3-C.sub.6)-cycloalkenyl, (C.sub.3-C.sub.6)-cycloalkyl-(C.sub.1-C.sub.6)-alkyl, (C.sub.3-C.sub.6)-cycloalkenyl-(C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-alkyl-O—(C.sub.1-C.sub.6)-alkyl, where the eight latter radicals are substituted by s radicals from the group consisting of nitro, halogen, cyano, (C.sub.1-C.sub.6)-alkyl, halo-(C.sub.1-C.sub.6)-alkyl, (C.sub.3-C.sub.6)-cycloalkyl, (C.sub.3-C.sub.6)-cycloalkenyl, R.sup.10O(O)C, (R.sup.10).sub.2N(O)C, R.sup.10O, (R.sup.10).sub.2N, R.sup.11(O).sub.nS, R.sup.10O(O).sub.2S, (R.sup.10).sub.2N(O).sub.2S and R.sup.10O—(C.sub.1-C.sub.6)-alkyl and oxo bear, or R.sup.13 represents phenyl, phenyl-(C.sub.1-C.sub.6)-alkyl, heteroaryl, heteroaryl-(C.sub.1-C.sub.6)-alkyl, heterocyclyl, heterocyclyl-(C.sub.1-C.sub.6)-alkyl, phenyl-O—(C.sub.1-C.sub.6)-alkyl, heteroaryl-O—(C.sub.1-C.sub.6)-alkyl, heterocyclyl-O—(C.sub.1-C.sub.6)-alkyl, phenyl-N(R.sup.10)—(C.sub.1-C.sub.6)-alkyl, heteroaryl-N(R.sup.10)—(C.sub.1-C.sub.6)-alkyl, heterocyclyl-N(R.sup.10)—(C.sub.1-C.sub.6)-alkyl, phenyl-S(O).sub.n—(C.sub.1-C.sub.6)-alkyl, heteroaryl-S(O).sub.n—(C.sub.1-C.sub.6)-alkyl or heterocyclyl-S(O).sub.n—(C.sub.1-C.sub.6)-alkyl, where the radicals are each substituted by m radicals from the group consisting of nitro, halogen, cyano, (C.sub.1-C.sub.6)-alkyl, halo-(C.sub.1-C.sub.6)-alkyl, (C.sub.3-C.sub.6)-cycloalkyl, (C.sub.3-C.sub.6)-cycloalkenyl, R.sup.10O(O)C, (R.sup.10).sub.2N(O)C, R.sup.10O, (R.sup.10).sub.2N, R.sup.11(O).sub.nS, R.sup.10O(O).sub.2S, (R.sup.10).sub.2N(O).sub.2S and R.sup.10O—(C.sub.1-C.sub.6)-alkyl, and where (C.sub.3-C.sub.6)-cycloalkyl, (C.sub.3-C.sub.6)-cycloalkenyl and heterocyclyl each independently bear n oxo groups, R.sup.14 represents (C.sub.1-C.sub.6)-alkyl, (C.sub.2-C.sub.6)-alkenyl, (C.sub.2-C.sub.6)-alkynyl, (C.sub.3-C.sub.6)-cycloalkyl, (C.sub.3-C.sub.6)-cycloalkenyl, (C.sub.3-C.sub.6)-cycloalkyl-(C.sub.1-C.sub.6)-alkyl, (C.sub.3-C.sub.6)-cycloalkenyl-(C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-alkyl-O—(C.sub.1-C.sub.6)-alkyl, where the eight latter radicals are substituted by s radicals from the group consisting of nitro, halogen, cyano, (C.sub.1-C.sub.6)-alkyl, halo-(C.sub.1-C.sub.6)-alkyl, (C.sub.3-C.sub.6)-cycloalkyl, (C.sub.3-C.sub.6)-cycloalkenyl, R.sup.10O(O)C, (R.sup.10).sub.2N(O)C, R.sup.10O, (R.sup.10).sub.2N, R.sup.11(O).sub.nS, R.sup.10O(O).sub.2S, (R.sup.10).sub.2N(O).sub.2S and R.sup.10O—(C.sub.1-C.sub.6)-alkyl and oxo bear, or R.sup.14 represents phenyl, phenyl-(C.sub.1-C.sub.6)-alkyl, heteroaryl, heteroaryl-(C.sub.1-C.sub.6)-alkyl, heterocyclyl, heterocyclyl-(C.sub.1-C.sub.6)-alkyl, phenyl-O—(C.sub.1-C.sub.6)-alkyl, heteroaryl-O—(C.sub.1-C.sub.6)-alkyl, heterocyclyl-O—(C.sub.1-C.sub.6)-alkyl, phenyl-N(R.sup.10)—(C.sub.1-C.sub.6)-alkyl, heteroaryl-N(R.sup.10)—(C.sub.1-C.sub.6)-alkyl, heterocyclyl-N(R.sup.10)—(C.sub.1-C.sub.6)-alkyl, phenyl-S(O).sub.n—(C.sub.1-C.sub.6)-alkyl, heteroaryl-S(O).sub.n—(C.sub.1-C.sub.6)-alkyl or heterocyclyl-S(O).sub.n—(C.sub.1-C.sub.6)-alkyl, where the radicals are each substituted by m radicals from the group consisting of nitro, halogen, cyano, (C.sub.1-C.sub.6)-alkyl, halo-(C.sub.1-C.sub.6)-alkyl, (C.sub.3-C.sub.6)-cycloalkyl, (C.sub.3-C.sub.6)-cycloalkenyl, R.sup.10O(O)C, (R.sup.10).sub.2N(O)C, R.sup.10O, (R.sup.10).sub.2N, R.sup.11(O).sub.nS, R.sup.10O(O).sub.2S, (R.sup.10).sub.2N(O).sub.2S and R.sup.10O—(C.sub.1-C.sub.6)-alkyl, and where (C.sub.3-C.sub.6)-cycloalkyl, (C.sub.3-C.sub.6)-cycloalkenyl and heterocyclyl each independently bear n oxo groups, R.sup.17, R.sup.18 and R.sup.19 independently represent R.sup.13 or R.sup.14S(O).sub.2, (R.sup.13).sub.2NS(O).sub.2, R.sup.13O S(O).sub.2, R.sup.13C(O), (R.sup.13).sub.2NC(O), (R.sup.13).sub.2NC(S), R.sup.13OC(O), R.sup.13OC(O)C(O), (R.sup.13).sub.2NC(O)C(O), or the (R.sup.17 and R.sup.18) or (R.sup.17 and R.sup.19) radicals form a ring with the carbon atom, or with the heteroatom or with the heteroatoms via which they are bonded, specifically a cycloalkyl, cycloalkenyl, heterocyclyl, heterocyclenyl, heteroaryl, arylheterocyclyl, arylheterocyclenyl, heteroarylheterocyclyl, heteroarylheterocyclenyl, heterocyclylheteroaryl or heterocyclenylheteroaryl, where each of these rings in turn is substituted by m radicals from the group consisting of nitro, halogen, cyano, thiocyano, (C.sub.1-C.sub.6)-alkyl, halo-(C.sub.1-C.sub.6)-alkyl, (C.sub.3-C.sub.6)-cycloalkyl, (C.sub.3-C.sub.6)-cycloalkenyl, R.sup.10O(O)C, (R.sup.10).sub.2N(O)C, R.sup.10O, (R.sup.10).sub.2N, R.sup.11(O).sub.nS, R.sup.10O(O).sub.2S, (R.sup.10).sub.2N(O).sub.2S and R.sup.10O—(C.sub.1-C.sub.6)-alkyl and oxo, m represents 0 or 1, 2, 3, 4 or 5, n represents 0, 1 or 2, s represents 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10 or 11.
4. The compound of formula (I) and/or salt as claimed in claim 1, in which R.sup.1 represents cyclopropyl, where the cyclopropyl group is substituted by s radicals from the group consisting of halogen, (C.sub.1-C.sub.6)-alkyl and halo-(C.sub.1-C.sub.6)-alkyl, R.sup.2 represents (R.sup.17) (R.sup.18) N(R.sup.19)N or R.sup.17R.sup.18C═N—(R.sup.19)N, R.sup.3 represents hydrogen, cyano, fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, difluoromethyl, cyclopropyl, hydroxycarbonyl, methoxycarbonyl, ethoxycarbonyl, methoxy, ethoxy, methylsulfanyl, methylsulfinyl or methylsulfonyl, R.sup.4, R.sup.5, R.sup.6 and R.sup.7 each independently represent hydrogen, cyano, fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, difluoromethyl, cyclopropyl, hydroxycarbonyl, methoxycarbonyl, ethoxycarbonyl, methoxy, ethoxy, methylsulfanyl, methylsulfinyl or methylsulfonyl, R.sup.8 represents hydrogen, (C.sub.1-C.sub.6)-alkyl, (C.sub.2-C.sub.6)-alkenyl, (C.sub.2-C.sub.6)-alkynyl, (C.sub.3-C.sub.6)-cycloalkyl, (C.sub.3-C.sub.6)-cycloalkenyl, (C.sub.3-C.sub.6)-cycloalkyl-(C.sub.1-C.sub.6)-alkyl, (C.sub.3-C.sub.6)-cycloalkenyl-(C.sub.1-C.sub.6)-alkyl, where the seven latter radicals bear s halogens, or R.sup.8 represents phenyl, phenyl-(C.sub.1-C.sub.6)-alkyl, heteroaryl, heteroaryl-(C.sub.1-C.sub.6)-alkyl, heterocyclyl, heterocyclyl-(C.sub.1-C.sub.6)-alkyl, phenyl-O—(C.sub.1-C.sub.6)-alkyl, heteroaryl-O—(C.sub.1-C.sub.6)-alkyl, heterocyclyl-O—(C.sub.1-C.sub.6)-alkyl, phenyl-N(R.sup.10)—(C.sub.1-C.sub.6)-alkyl, heteroaryl-N(R.sup.10)—(C.sub.1-C.sub.6)-alkyl, heterocyclyl-N(R.sup.10)—(C.sub.1-C.sub.6)-alkyl, where the radicals are each substituted by m radicals from the group consisting of nitro, halogen, cyano, (C.sub.1-C.sub.6)-alkyl, halo-(C.sub.1-C.sub.6)-alkyl, (C.sub.3-C.sub.6)-cycloalkyl, (C.sub.3-C.sub.6)-cycloalkenyl, R.sup.10O(O)C, (R.sup.10).sub.2N(O)C, R.sup.10O, (R.sup.10).sub.2N, R.sup.11(O).sub.nS, R.sup.10O(O).sub.2S, (R.sup.10).sub.2N(O).sub.2S and R.sup.10O—(C.sub.1-C.sub.6)-alkyl, and where (C.sub.3-C.sub.6)-cycloalkyl, (C.sub.3-C.sub.6)-cycloalkenyl and heterocyclyl each independently bear n oxo groups, or the R.sup.8 radicals form a ring with the heteroatom or with the heteroatoms via which they are bonded, specifically a heterocyclyl, heterocyclenyl, heteroaryl, arylheterocyclyl, arylheterocyclenyl, heteroarylheterocyclyl, heteroarylheterocyclenyl, heterocyclylheteroaryl or heterocyclenylheteroaryl, where each of these rings in turn is substituted by m radicals from the group consisting of nitro, halogen, cyano, (C.sub.1-C.sub.6)-alkyl, halo-(C.sub.1-C.sub.6)-alkyl, (C.sub.3-C.sub.6)-cycloalkyl, (C.sub.3-C.sub.6)-cycloalkenyl, R.sup.10O(O)C, (R.sup.10).sub.2N(O)C, R.sup.10O, (R.sup.10).sub.2N, R.sup.11(O).sub.nS, R.sup.10O(O).sub.2S, (R.sup.10).sub.2N(O).sub.2S and R.sup.10O—(C.sub.1-C.sub.6)-alkyl and oxo, R.sup.9 represents (C.sub.1-C.sub.6)-alkyl, (C.sub.3-C.sub.6)-cycloalkyl-(C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-alkyl-O—(C.sub.1-C.sub.6)-alkyl, (C.sub.3-C.sub.6)-cycloalkyl-(C.sub.1-C.sub.6)-alkyl-O—(C.sub.1-C.sub.6)-alkyl, phenyl, phenyl-(C.sub.1-C.sub.6)-alkyl, heteroaryl, heteroaryl-(C.sub.1-C.sub.6)-alkyl, heterocyclyl, heterocyclyl-(C.sub.1-C.sub.6)-alkyl, phenyl-O—(C.sub.1-C.sub.6)-alkyl, heteroaryl-O—(C.sub.1-C.sub.6)-alkyl or heterocyclyl-O—(C.sub.1-C.sub.6)-alkyl, where the nine latter radicals are each substituted by m radicals from the group consisting of nitro, halogen, (C.sub.1-C.sub.6)-alkyl, halo-(C.sub.1-C.sub.6)-alkyl, R.sup.10O(O)C, (R.sup.10).sub.2N(O)C, R.sup.10O, (R.sup.10).sub.2N, R.sup.11(O).sub.nS and R.sup.10O—(C.sub.1-C.sub.6)-alkyl, and where heterocyclyl bears n oxo groups, R.sup.10 represents hydrogen or (C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-haloalkyl R.sup.11 represents (C.sub.1-C.sub.6)-alkyl, R.sup.12 represents (C.sub.1-C.sub.4)-alkyl, R.sup.13 represents hydrogen, (C.sub.1-C.sub.6)-alkyl, (C.sub.2-C.sub.6)-alkenyl, (C.sub.2-C.sub.6)-alkynyl, (C.sub.3-C.sub.6)-cycloalkyl, (C.sub.3-C.sub.6)-cycloalkenyl, (C.sub.3-C.sub.6)-cycloalkyl-(C.sub.1-C.sub.6)-alkyl, (C.sub.3-C.sub.6)-cycloalkenyl-(C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-alkyl-O—(C.sub.1-C.sub.6)-alkyl, where the eight latter radicals are substituted by s radicals from the group consisting of nitro, halogen, cyano, (C.sub.1-C.sub.6)-alkyl, halo-(C.sub.1-C.sub.6)-alkyl, (C.sub.3-C.sub.6)-cycloalkyl, (C.sub.3-C.sub.6)-cycloalkenyl, R.sup.10O(O)C, (R.sup.10).sub.2N(O)C, R.sup.10O, (R.sup.10).sub.2N, R.sup.11(O).sub.nS, R.sup.10O(O).sub.2S, (R.sup.10).sub.2N(O).sub.2S and R.sup.10O—(C.sub.1-C.sub.6)-alkyl and oxo, or R.sup.13 represents phenyl, phenyl-(C.sub.1-C.sub.6)-alkyl, heteroaryl, heteroaryl-(C.sub.1-C.sub.6)-alkyl, heterocyclyl, heterocyclyl-(C.sub.1-C.sub.6)-alkyl, phenyl-O—(C.sub.1-C.sub.6)-alkyl, heteroaryl-O—(C.sub.1-C.sub.6)-alkyl, heterocyclyl-O—(C.sub.1-C.sub.6)-alkyl, phenyl-N(R.sup.10)—(C.sub.1-C.sub.6)-alkyl, heteroaryl-N(R.sup.10)—(C.sub.1-C.sub.6)-alkyl, heterocyclyl-N(R.sup.10)—(C.sub.1-C.sub.6)-alkyl, where the radicals are each substituted by m radicals from the group consisting of nitro, halogen, cyano, (C.sub.1-C.sub.6)-alkyl, halo-(C.sub.1-C.sub.6)-alkyl, (C.sub.3-C.sub.6)-cycloalkyl, (C.sub.3-C.sub.6)-cycloalkenyl, R.sup.10O(O)C, (R.sup.10).sub.2N(O)C, R.sup.10O, (R.sup.10).sub.2N, R.sup.11(O).sub.nS, R.sup.10O(O).sub.2S, (R.sup.10).sub.2N(O).sub.2S and R.sup.10O—(C.sub.1-C.sub.6)-alkyl, and where (C.sub.3-C.sub.6)-cycloalkyl, (C.sub.3-C.sub.6)-cycloalkenyl and heterocyclyl each independently bear n oxo groups, R.sup.14 represents (C.sub.1-C.sub.6)-alkyl, (C.sub.2-C.sub.6)-alkenyl, (C.sub.2-C.sub.6)-alkynyl, (C.sub.3-C.sub.6)-cycloalkyl, (C.sub.3-C.sub.6)-cycloalkenyl, (C.sub.3-C.sub.6)-cycloalkyl-(C.sub.1-C.sub.6)-alkyl, (C.sub.3-C.sub.6)-cycloalkenyl-(C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-alkyl-O—(C.sub.1-C.sub.6)-alkyl, where the eight latter radicals are substituted by s radicals from the group consisting of nitro, halogen, cyano, (C.sub.1-C.sub.6)-alkyl, halo-(C.sub.1-C.sub.6)-alkyl, (C.sub.3-C.sub.6)-cycloalkyl, (C.sub.3-C.sub.6)-cycloalkenyl, R.sup.10O(O)C, (R.sup.10).sub.2N(O)C, R.sup.10O, (R.sup.10).sub.2N, R.sup.11(O).sub.nS, R.sup.10O(O).sub.2S, (R.sup.10).sub.2N(O).sub.2S and R.sup.10O—(C.sub.1-C.sub.6)-alkyl and oxo, or R.sup.14 represents phenyl, phenyl-(C.sub.1-C.sub.6)-alkyl, heteroaryl, heteroaryl-(C.sub.1-C.sub.6)-alkyl, heterocyclyl, heterocyclyl-(C.sub.1-C.sub.6)-alkyl, phenyl-O—(C.sub.1-C.sub.6)-alkyl, heteroaryl-O—(C.sub.1-C.sub.6)-alkyl, heterocyclyl-O—(C.sub.1-C.sub.6)-alkyl, phenyl-N(R.sup.10)—(C.sub.1-C.sub.6)-alkyl, heteroaryl-N(R.sup.10)—(C.sub.1-C.sub.6)-alkyl, heterocyclyl-N(R.sup.10)—(C.sub.1-C.sub.6)-alkyl, where the radicals are each substituted by m radicals from the group consisting of nitro, halogen, cyano, (C.sub.1-C.sub.6)-alkyl, halo-(C.sub.1-C.sub.6)-alkyl, (C.sub.3-C.sub.6)-cycloalkyl, (C.sub.3-C.sub.6)-cycloalkenyl, R.sup.10O(O)C, (R.sup.10).sub.2N(O)C, R.sup.10O, (R.sup.10).sub.2N, R.sub.11(O).sub.nS, R.sup.10O(O).sub.2S, (R.sup.10).sub.2N(O).sub.2S and R.sup.10O—(C.sub.1-C.sub.6)-alkyl, and where (C.sub.3-C.sub.6)-cycloalkyl, (C.sub.3-C.sub.6)-cycloalkenyl and heterocyclyl each independently bear n oxo groups, R.sup.17 and R.sup.18 independently represent R.sup.13 or R.sup.14S(O).sub.2, (R.sup.13).sub.2NS(O).sub.2, R.sup.13O S(O).sub.2, R.sup.13C(O), (R.sup.13).sub.2NC(O), (R.sup.13).sub.2NC(S), R.sup.13O C(O), R.sup.13O C(O)C(O), (R.sup.13).sub.2NC(O)C(O), or the R.sup.17 and R.sup.18 radicals form a ring with the carbon atom, or with the heteroatom via which they are bonded, specifically a cycloalkyl, cycloalkenyl, heterocyclyl, heterocyclenyl, heteroaryl, arylheterocyclyl, arylheterocyclenyl, heteroarylheterocyclyl, heteroarylheterocyclenyl, heterocyclylheteroaryl or heterocyclenylheteroaryl, where each of these rings in turn is substituted by m radicals from the group consisting of nitro, halogen, cyano, (C.sub.1-C.sub.6)-alkyl, halo-(C.sub.1-C.sub.6)-alkyl, (C.sub.3-C.sub.6)-cycloalkyl, (C.sub.3-C.sub.6)-cycloalkenyl, R.sup.10O(O)C, (R.sup.10).sub.2N(O)C, R.sup.10O, (R.sup.10).sub.2N, R.sup.11(O).sub.nS, R.sup.10O(O).sub.2S, (R.sup.10).sub.2N(O).sub.2S and R.sup.10O—(C.sub.1-C.sub.6)-alkyl and oxo, R.sup.19 represents hydrogen or (C.sub.1-C.sub.6)-alkyl, m represents 0, 1, 2 or 3, n represents 0, 1 or 2, s represents 0, 1, 2, 3, 4 or 5.
5. The compound of formula (I) and/or salt as claimed in claim 1, in which R.sup.1 represents cyclopropyl, R.sup.2 represents (R.sup.17) (R.sup.18) N(R.sup.19)N or R.sup.17R.sup.18C═N—(R.sup.19)N, R.sup.3 represents cyano, fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, difluoromethyl, cyclopropyl, hydroxycarbonyl, methoxycarbonyl, ethoxycarbonyl, methoxy, ethoxy, methylsulfanyl, methylsulfinyl or methylsulfonyl, R.sup.4, R.sup.5, R.sup.6 and R.sup.7 each independently represent hydrogen, cyano, fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, difluoromethyl, cyclopropyl, hydroxycarbonyl, methoxycarbonyl, ethoxycarbonyl, methoxy, ethoxy, methylsulfanyl, methylsulfinyl or methylsulfonyl, R.sup.8 represents hydrogen, (C.sub.1-C.sub.6)-alkyl, (C.sub.2-C.sub.6)-alkenyl and (C.sub.3-C.sub.6)-cycloalkyl, where the three latter radicals bear s halogens, or R.sup.8 represents phenyl, phenyl-(C.sub.1-C.sub.6)-alkyl, heteroaryl, heteroaryl-(C.sub.1-C.sub.6)-alkyl, heterocyclyl, heterocyclyl-(C.sub.1-C.sub.6)-alkyl, where the radicals are each substituted by m radicals from the group consisting of nitro, halogen, cyano, (C.sub.1-C.sub.6)-alkyl, halo-(C.sub.1-C.sub.6)-alkyl, (C.sub.3-C.sub.6)-cycloalkyl, (C.sub.3-C.sub.6)-cycloalkenyl, R.sup.10O(O)C, (R.sup.10).sub.2N(O)C, R.sup.10O, (R.sup.10).sub.2N, R.sup.11(O).sub.nS, R.sup.10O(O).sub.2S, (R.sup.10).sub.2N(O).sub.2S and R.sup.10O—(C.sub.1-C.sub.6)-alkyl, and where (C.sub.3-C.sub.6)-cycloalkyl, (C.sub.3-C.sub.6)-cycloalkenyl and heterocyclyl each independently bear n oxo groups, or the R.sup.8 radicals form a ring with the heteroatom or with the heteroatoms via which they are bonded, specifically a heterocyclyl, heterocyclenyl, heteroaryl, arylheterocyclyl, arylheterocyclenyl, heteroarylheterocyclyl, heteroarylheterocyclenyl, heterocyclylheteroaryl or heterocyclenylheteroaryl, where each of these rings in turn is substituted by m radicals from the group consisting of nitro, halogen, cyano, (C.sub.1-C.sub.6)-alkyl, halo-(C.sub.1-C.sub.6)-alkyl, (C.sub.3-C.sub.6)-cycloalkyl, (C.sub.3-C.sub.6)-cycloalkenyl, R.sup.10O(O)C, (R.sup.10).sub.2N(O)C, R.sup.10O, (R.sup.10).sub.2N, R.sup.11(O).sub.nS, R.sup.10O(O).sub.2S, (R.sup.10).sub.2N(O).sub.2S and R.sup.10O—(C.sub.1-C.sub.6)-alkyl and oxo, R.sup.9 represents (C.sub.1-C.sub.6)-alkyl, phenyl, phenyl-(C.sub.1-C.sub.6)-alkyl, heteroaryl, heteroaryl-(C.sub.1-C.sub.6)-alkyl, heterocyclyl, heterocyclyl-(C.sub.1-C.sub.6)-alkyl, where the seven latter radicals are each substituted by m radicals from the group consisting of nitro, halogen, (C.sub.1-C.sub.6)-alkyl, halo-(C.sub.1-C.sub.6)-alkyl, R.sup.10O(O)C, (R.sup.10).sub.2N(O)C, R.sup.10O, (R.sup.10).sub.2N, R.sup.11(O).sub.nS and R.sup.10O—(C.sub.1-C.sub.6)-alkyl, and where heterocyclyl bears n oxo groups, R.sup.10 represents hydrogen or (C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-haloalkyl R.sup.11 represents (C.sub.1-C.sub.6)-alkyl, R.sup.12 represents (C.sub.1-C.sub.4)-alkyl, R.sup.13 represents hydrogen, (C.sub.1-C.sub.6)-alkyl, (C.sub.2-C.sub.6)-alkenyl, (C.sub.2-C.sub.6)-alkynyl, (C.sub.3-C.sub.6)-cycloalkyl, (C.sub.3-C.sub.6)-cycloalkenyl, (C.sub.3-C.sub.6)-cycloalkyl-(C.sub.1-C.sub.6)-alkyl, (C.sub.3-C.sub.6)-cycloalkenyl-(C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-alkyl-O—(C.sub.1-C.sub.6)-alkyl, where the eight latter radicals are substituted by s radicals from the group consisting of nitro, halogen, cyano, (C.sub.1-C.sub.6)-alkyl, halo-(C.sub.1-C.sub.6)-alkyl, (C.sub.3-C.sub.6)-cycloalkyl, (C.sub.3-C.sub.6)-cycloalkenyl, R.sup.10O(O)C, (R.sup.10).sub.2N(O)C, R.sup.10O, (R.sup.10).sub.2N, R.sup.11(O).sub.nS, R.sup.10O(O).sub.2S, (R.sup.10).sub.2N(O).sub.2S and R.sup.10O—(C.sub.1-C.sub.6)-alkyl and oxo, or represents phenyl, phenyl-(C.sub.1-C.sub.6)-alkyl, heteroaryl, heteroaryl-(C.sub.1-C.sub.6)-alkyl, heterocyclyl, heterocyclyl-(C.sub.1-C.sub.6)-alkyl, phenyl-O—(C.sub.1-C.sub.6)-alkyl, heteroaryl-O—(C.sub.1-C.sub.6)-alkyl, heterocyclyl-O—(C.sub.1-C.sub.6)-alkyl, phenyl-N(R.sup.10)—(C.sub.1-C.sub.6)-alkyl, heteroaryl-N(R.sup.10)—(C.sub.1-C.sub.6)-alkyl, heterocyclyl-N(R.sup.10)—(C.sub.1-C.sub.6)-alkyl, where the radicals are each substituted by m radicals from the group consisting of nitro, halogen, cyano, (C.sub.1-C.sub.6)-alkyl, halo-(C.sub.1-C.sub.6)-alkyl, (C.sub.3-C.sub.6)-cycloalkyl, (C.sub.3-C.sub.6)-cycloalkenyl, R.sup.10O(O)C, (R.sup.10).sub.2N(O)C, R.sup.10O, (R.sup.10).sub.2N, R.sup.11(O).sub.nS, R.sup.10O(O).sub.2S, (R.sup.10).sub.2N(O).sub.2S and R.sup.10O—(C.sub.1-C.sub.6)-alkyl, and where (C.sub.3-C.sub.6)-cycloalkyl, (C.sub.3-C.sub.6)-cycloalkenyl and heterocyclyl each independently bear n oxo groups, or the R.sup.13 radicals form a ring with the heteroatom or with the heteroatoms via which they are bonded, specifically a heterocyclyl, heterocyclenyl, heteroaryl, arylheterocyclyl, arylheterocyclenyl, heteroarylheterocyclyl, heteroarylheterocyclenyl, heterocyclylheteroaryl or heterocyclenylheteroaryl, where each of these rings in turn is substituted by m radicals from the group consisting of nitro, halogen, cyano, (C.sub.1-C.sub.6)-alkyl, halo-(C.sub.1-C.sub.6)-alkyl, (C.sub.3-C.sub.6)-cycloalkyl, (C.sub.3-C.sub.6)-cycloalkenyl, R.sup.10O(O)C, (R.sup.10).sub.2N(O)C, R.sup.10O, (R.sup.10).sub.2N, R.sup.11(O).sub.nS, R.sup.10O(O).sub.2S, (R.sup.10).sub.2N(O).sub.2S and R.sup.10O—(C.sub.1-C.sub.6)-alkyl and oxo, R.sup.14 represents (C.sub.1-C.sub.6)-alkyl, (C.sub.2-C.sub.6)-alkenyl, (C.sub.2-C.sub.6)-alkynyl, (C.sub.3-C.sub.6)-cycloalkyl, (C.sub.3-C.sub.6)-cycloalkenyl, (C.sub.3-C.sub.6)-cycloalkyl-(C.sub.1-C.sub.6)-alkyl, (C.sub.3-C.sub.6)-cycloalkenyl-(C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-alkyl-O—(C.sub.1-C.sub.6)-alkyl, where the eight latter radicals are substituted by s radicals from the group consisting of nitro, halogen, cyano, (C.sub.1-C.sub.6)-alkyl, halo-(C.sub.1-C.sub.6)-alkyl, (C.sub.3-C.sub.6)-cycloalkyl, (C.sub.3-C.sub.6)-cycloalkenyl, R.sup.10O(O)C, (R.sup.10).sub.2N(O)C, R.sup.10O, (R.sup.10).sub.2N, R.sup.11(O).sub.nS, R.sup.10O(O).sub.2S, (R.sup.10).sub.2N(O).sub.2S and R.sup.10O—(C.sub.1-C.sub.6)-alkyl and oxo, or R.sup.14 represents phenyl, phenyl-(C.sub.1-C.sub.6)-alkyl, heteroaryl, heteroaryl-(C.sub.1-C.sub.6)-alkyl, heterocyclyl, heterocyclyl-(C.sub.1-C.sub.6)-alkyl, phenyl-O—(C.sub.1-C.sub.6)-alkyl, heteroaryl-O—(C.sub.1-C.sub.6)-alkyl, heterocyclyl-O—(C.sub.1-C.sub.6)-alkyl, phenyl-N(R.sup.10)—(C.sub.1-C.sub.6)-alkyl, heteroaryl-N(R.sup.10)—(C.sub.1-C.sub.6)-alkyl, heterocyclyl-N(R.sup.10)—(C.sub.1-C.sub.6)-alkyl, where the radicals are each substituted by m radicals from the group consisting of nitro, halogen, cyano, (C.sub.1-C.sub.6)-alkyl, halo-(C.sub.1-C.sub.6)-alkyl, (C.sub.3-C.sub.6)-cycloalkyl, (C.sub.3-C.sub.6)-cycloalkenyl, R.sup.10O(O)C, (R.sup.10).sub.2N(O)C, R.sup.10O, (R.sup.10).sub.2N, R.sup.11(O).sub.nS, R.sup.10O(O).sub.2S, (R.sup.10).sub.2N(O).sub.2S and R.sup.10O—(C.sub.1-C.sub.6)-alkyl, and where (C.sub.3-C.sub.6)-cycloalkyl, (C.sub.3-C.sub.6)-cycloalkenyl and heterocyclyl each independently bear n oxo groups, R.sup.17 and R.sup.18 independently represent R.sup.13 or R.sup.14S(O).sub.2, (R.sup.13).sub.2NS(O).sub.2, R.sup.13OS(O).sub.2, R.sup.13C(O), (R.sup.13).sub.2NC(O), (R.sup.13).sub.2NC(S), R.sup.13OC(O)C(O), (R.sup.13).sub.2NC(O)C(O), or the R.sup.17 and R.sup.18 radicals form a ring with the heteroatom via which they are bonded, specifically a heterocyclyl, heterocyclenyl, heteroaryl, arylheterocyclyl, arylheterocyclenyl, heteroarylheterocyclyl, heteroarylheterocyclenyl, heterocyclylheteroaryl or heterocyclenylheteroaryl, where each of these rings in turn is substituted by m radicals from the group consisting of nitro, halogen, cyano, (C.sub.1-C.sub.6)-alkyl, halo-(C.sub.1-C.sub.6)-alkyl, (C.sub.3-C.sub.6)-cycloalkyl, (C.sub.3-C.sub.6)-cycloalkenyl, R.sup.10O(O)C, (R.sup.10).sub.2N(O)C, R.sup.10O, (R.sup.10).sub.2N, R.sup.11(O).sub.nS, R.sup.10O(O).sub.2S, (R.sup.10).sub.2N(O).sub.2S and R.sup.10O—(C.sub.1-C.sub.6)-alkyl and oxo, R.sup.19 represents hydrogen or (C.sub.1-C.sub.6)-alkyl, m represents 0, 1, 2 or 3, n represents 0, 1 or 2, s represents 0, 1, 2, 3, 4 or 5.
6. An herbicidal composition comprising at least one compound of formula (I) and/or salt as claimed in claim 1 mixed with one or more formulation auxiliaries.
7. The herbicidal composition as claimed in claim 6, comprising at least one further pesticidally active substance selected from the group consisting of insecticides, acaricides, herbicides, fungicides, safeners and growth regulators.
8. A method for controlling one or more unwanted plants, comprising applying an effective amount of at least one compound of formula (I) and/or salt as claimed in claim 1 or of an herbicidal composition thereof to the plants and/or to a site of unwanted vegetation.
9. A product comprising the compound of formula (I) and/or salt as claimed in claim 1 or an herbicidal composition thereof for controlling one or more unwanted plants.
10. The product as claimed in claim 9, wherein the compound of formula (I) and/or salt is used for controlling one or more unwanted plants in one or more crops of one or more useful plants.
11. The product as claimed in claim 10, wherein the useful plants are transgenic useful plants.
Description
A. CHEMICAL EXAMPLES
Preparation of 5-(2-chlorophenyl)-2-cyclopropyl-N-methylpyrimidine-4-carbohydrazide (Example I-500)
[0476] To an initial charge of 200 mg (0.728 mmol) of 5-(2-chlorophenyl)-2-cyclopropylpyrimidine-4-carboxylic acid, 173 mg (2.184 mmol) of pyridine, 221 mg (2.184 mmol) of triethylamine and 67.0 mg (1.456 mmol) of methylhydrazine in 5 ml of acetonitrile under nitrogen is added 695 mg (1.095 mmol) of a 50% T3P solution in THF, and the mixture is heated under reflux for 5 h. After the reaction has ended, the mixture is cooled to room temperature, diluted with water, treated with 291 mg (7.281 mmol) of a 6N NaOH solution and extracted with ethyl acetate, and the organic phase is dried over sodium sulfate.
[0477] Purification using silica gel affords 134 mg (58% yield) of the desired product as a colorless resin.
[0478] .sup.1H-NMR (CDCl.sub.3, 400 MHz): 8.62, 8.60 (2s, 1H); 7.5-7.3 (m, 4H); 4.4, 3.75 (2bs, 2H), 3.09, 3.02 (2s, 3H); 2.34 (m, 1H); 1.26-1.1 (m, 4H).
Preparation of 5-(2-chlorophenyl)-2-cyclopropyl-N′,N′-dimethylpyrimidine-4-carbohydrazide (Example I-501)
[0479] To an initial charge of 250.0 mg (0.910 mmol) of 5-(2-chlorophenyl)-2-cyclopropylpyrimidine-4-carboxylic acid, 216.0 mg (2.730 mmol) of pyridine, 276.0 mg (2.730 mmol) of triethylamine and 109.0 mg (1.820 mmol) of 1,1-dimethylhydrazine in 5 ml of acetonitrile under nitrogen is added 869 mg (1.365 mmol) of a 50% T3P solution in THF, and the mixture is heated under reflux for 5 h. After the reaction has ended, the mixture is cooled to room temperature, diluted with water, treated with 364 mg (9.101 mmol) of a 6N NaOH solution and extracted with ethyl acetate, and the organic phase is dried over sodium sulfate.
[0480] Purification using silica gel affords 150 mg (93% yield) of the desired product as a yellowish resin.
[0481] For NMR data see above (NMR peak list)
Preparation of tert-butyl 2-{[5-(2-chlorophenyl)-2-cyclopropylpyrimidin-4-yl]carbonyl}-1-methylhydrazinecarboxylate (Example I-548)
[0482] Analogously to the above method, 250.0 mg (0.910 mmol) of 5-(2-chlorophenyl)-2-cyclopropylpyrimidine-4-carboxylic acid, 691 mg (8.737 mmol) of pyridine, 884 mg (8.737 mmol) of triethylamine and 511.0 mg (3.495 mmol) of tert-butyl 1-methylhydrazinecarboxylate in 15 ml of acetonitrile and 2.780 g (4.368 mmol) of a 50% T3P solution in THF are used to obtain, after reflux for 5 h, 1.130 g (92% yield) of a solid after workup and column chromatography.
[0483] .sup.1H-NMR (CDCl.sub.3, 400 MHz): 8.63 (d, 1H); 8.58 (s, 1H), 8.18 (d, 1H); 7.7.-7.2 (m, 5H), 6.79 (m, 2H); 6.69 (d, 1H); 2.42 (m, 1H); 1.30-1.15 (m, 4H).
Preparation of 5-(2-chlorophenyl)-2-cyclopropyl-N′-(pyridin-2-yl)pyrimidine-4-carbohydrazide (Example I-510)
[0484] Analogously to the above method, 200.0 mg (0.910 mmol) of 5-(2-chlorophenyl)-2-cyclopropylpyrimidine-4-carboxylic acid, 173.0 mg (2.184 mmol) of pyridine, 221.0 mg (2.184 mmol) of triethylamine and 87.0 mg (0.801 mmol) of 2-hydrazinopyridine in 3 ml of acetonitrile and 695 mg (1.092 mmol) of a 50% T3P solution in THF are used to obtain, after reflux for 5 h, 230 mg (76% yield; 90% purity) of a resin after workup and column chromatography.
[0485] For NMR data see above (NMR peak list)
Preparation of N′-acetyl-5-(2-chlorophenyl)-2-cyclopropyl-N′-(pyridin-2-yl)pyrimidine-4-carbohydrazide (Example I-513)
[0486] 170.0 mg (0.465 mmol) of 5-(2-chlorophenyl)-2-cyclopropyl-N′-(pyridin-2-yl)pyrimidine-4-carbohydrazide (example I-510) is dissolved in 3 ml of acetonitrile under nitrogen, 74.0 mg (0.929 mmol) of pyridine and then 142.0 mg (1.394 mmol) of acetic anhydride are added, and the mixture is stirred at room temperature for 48 h. This is followed by addition of water and 112 mg (2.788 mol) of sodium hydroxide, and extraction with ethyl acetate. Drying over sodium sulfate affords 73.0 mg (33% yield; 85% purity) of a yellow resin.
[0487] For NMR data see above (NMR peak list)
Preparation of 5-(2-chloro-6-methoxyphenyl)-2-cyclopropylpyrimidine-4-carbohydrazide (Example I-3349)
[0488] For this purpose, 10.7 mg (0.034 mmol) of methyl 5-(2-chloro-6-methoxyphenyl)-2-cyclopropylpyrimidine-4-carboxylate is heated at reflux with 2.546 mg (0.050 mmol) of hydrazine hydrate in 1 ml of methanol for 3.5 h. After the reaction has ended, the mixture is cooled down to room temperature and diluted with water, methanol is distilled off under reduced pressure, and the aqueous phase is extracted repeatedly with ethyl acetate. Drying over sodium sulfate affords 8.50 mg (76% yield) of the above compound.
[0489] For NMR data see above (NMR peak list)
Preparation of 5-(2-chlorophenyl)-2-(1-methylcyclopropyl)pyrimidine-4-carbohydrazide (Example I-560)
[0490] For this purpose, 160.0 mg (0.528 mmol) of methyl 5-(2-chlorophenyl)-2-(1-methylcyclopropyl)pyrimidine-4-carboxylate is heated at reflux with 40.085 mg (0.793 mmol) of hydrazine hydrate in 5 ml of methanol for 2.0 h. After the reaction has ended, the mixture is cooled down to room temperature and diluted with water, methanol is distilled off under reduced pressure, and the aqueous phase is extracted repeatedly with ethyl acetate. Drying over sodium sulfate affords 137 mg (81% yield) of the above compound.
[0491] For NMR data see above (NMR peak list)
Preparation of 5-(2-chlorophenyl)-2-cyclopropyl-N′-(tetrahydro-4H-pyran-4-ylidene)pyrimidine-4-carbohydrazide (Example I-559)
[0492] For this purpose, 160.0 mg (0.528 mmol) of 5-(2-chlorophenyl)-2-cyclopropylpyrimidine-4-carbohydrazide (I-497) is reacted with 78.0 mg (0.779 mmol) of tetrahydro-4H-pyran-4-one in 4 ml of acetonitrile and 16.0 mg (0.260 mmol) of acetic acid at room temperature over the course of 16 h. After the reaction has ended, the mixture is diluted with ethyl acetate and water, and washed with 42.0 mg (1.039 mmol) of sodium hydroxide and with water. Drying over sodium sulfate affords 160 mg (62% yield; 75% purity) of the above compound.
[0493] For NMR data see above (NMR peak list)
Preparation of 5-(2-chlorophenyl)-2-cyclopropyl-N′-(pyridin-2-ylcarbonyl)pyrimidine-4-carbohydrazide (Example I-527)
[0494] For this purpose, 150.0 mg (0.520 mmol) of 5-(2-chlorophenyl)-2-cyclopropylpyrimidine-4-carbohydrazide (I-497) are reacted with 70.0 mg (0.571 mg) of pyridine-2-carboxylic acid analogously to the above method (T3P coupling) in 3 ml. Workup and drying under reduced pressure affords 196 mg (86% yield; 90% purity) of a yellowish solid.
[0495] .sup.1H-NMR (CDCl.sub.3, 400 MHz): 8.62 (d, 1H); 8.51 (d, 1H), 8.15 (d, 1H); 7.86 (t, 1H), 7.50-7.20 (m, 7H), 2.43 (m, 1H); 1.33-1.21 (m, 4H).
Preparation of 5-(2-chlorophenyl)-2-cyclopropyl-N′-formylpyrimidine-4-carbohydrazide (Example I-516)
[0496] Analogously to the above method, 100.0 mg (0.364 mmol) of 5-(2-chlorophenyl)-2-cyclopropylpyrimidine-4-carboxylic acid, 86.0 mg (1.092 mmol) of pyridine, 111.0 mg (1.092 mmol) of triethylamine and 28.0 mg (0.473 mmol) of formohydrazide in 3 ml of acetonitrile and 347 g (0.546 mmol) of a 50% T3P solution in THF are used to obtain, after reflux for 5 h, 70.0 mg (55% yield; 90% purity) of an oil after workup and column chromatography.
[0497] .sup.1H-NMR (CDCl.sub.3, 400 MHz): 10.0 (bs, 1H), 9.25 (bs, 1H), 8.58 (s, 1H); 7.75 (s, 1H), 7.45 (d, 1H), 7.40-7.20 (m, 3H), 2.38 (m, 1H); 1.35-1.20 (m, 4H).
Preparation of ethyl 2-{[5-(2-chloro-4-fluorophenyl)-2-cyclopropylpyrimidin-4-yl]carbonyl}hydrazinecarboxylate (Example I-2591)
[0498] 73.0 mg (0.249 mmol) of 5-(2-chloro-4-fluorophenyl)-2-cyclopropylpyrimidine-4-carboxylic acid are dissolved in 2 ml of dichloromethane under nitrogen, 85.81 mg (0.848 mmol) of triethylamine and then 238.07 mg (0.374 mmol) of 50% solution of T3P in THF are added, and the mixture is cooled to 0° C. and reacted with 31.16 mg (0.299 mmol) of ethylhydrazine carboxylate. After stirring at room temperature for 16 h, the mixture is diluted with dichloromethane and washed with pH 5 buffer and then with water, and the organic phase is dried over sodium sulfate. 55.2 mg (56% yield) of the desired product is obtained as a yellowish oil.
[0499] For NMR data see above (NMR peak list)
Preparation of 2-{[5-(2-chlorophenyl)-2-cyclopropylpyrimidin-4-yl]carbonyl}-N-ethylhydrazinecarboxamide (Example I-552)
[0500] For this purpose, 115.0 mg (0.398 mmol) of 5-(2-chlorophenyl)-2-cyclopropylpyrimidine-4-carbohydrazide (I-497) and 32.0 mg (0.398 mmol) of pyridine are dissolved in 4 ml of dichloromethane under nitrogen, and reacted with 31.0 mg (0.438 mmol) of ethyl isocyanate at room temperature over the course of 120 h. After the reaction has ended, the mixture is freed of the solvent under reduced pressure. 155 mg (quantitative; 95% purity) of a colorless solid is obtained.
[0501] For NMR data see above (NMR peak list)
B. FORMULATION EXAMPLES
[0502] 1. Dusting Products
[0503] A dusting product is obtained by mixing 10 parts by weight of a compound of the formula (I) and 90 parts by weight of talc as an inert substance and comminuting the mixture in a hammer mill.
[0504] 2. Dispersible Powder
[0505] A readily water-dispersible wettable powder is obtained by mixing 25 parts by weight of a compound of the formula (I), 64 parts by weight of kaolin-containing quartz as an inert substance, 10 parts by weight of potassium lignosulfonate and 1 part by weight of sodium oleoylmethyltaurate as a wetting agent and dispersant, and grinding the mixture in a pinned-disk mill.
[0506] 3. Dispersion Concentrate
[0507] A readily water-dispersible dispersion concentrate is obtained by mixing 20 parts by weight of a compound of the formula (I), 6 parts by weight of alkylphenol polyglycol ether (*Triton X 207), 3 parts by weight of isotridecanol polyglycol ether (8 EO) and 71 parts by weight of paraffinic mineral oil (boiling range for example about 255 to more than 277° C.) and grinding the mixture in a friction ball mill to a fineness of below 5 microns.
[0508] 4. Emulsifiable Concentrate
[0509] An emulsifiable concentrate is obtained from 15 parts by weight of a compound of the formula (I), 75 parts by weight of cyclohexanone as a solvent and 10 parts by weight of ethoxylated nonylphenol as an emulsifier.
[0510] 5. Water-Dispersible Granules
[0511] Water-dispersible granules are obtained by mixing
[0512] 75 parts by weight of a compound of the formula (I),
[0513] 10 ″ of calcium lignosulfonate,
[0514] 5 ″ of sodium laurylsulfate,
[0515] 3 ″ of polyvinyl alcohol and
[0516] 7 ″ of kaolin,
[0517] grinding the mixture in a pinned-disk mill, and granulating the powder in a fluidized bed by spray application of water as a granulating liquid.
[0518] Water-dispersible granules are also obtained by homogenizing and precomminuting, in a colloid mill,
[0519] 25 parts by weight of a compound of the formula (I),
[0520] 5 ″ of sodium 2,2′-dinaphthylmethane-6,6′-disulfonate,
[0521] 2 ″ of sodium oleoylmethyltaurinate,
[0522] 1 ″ polyvinyl alcohol,
[0523] 17 ″ of calcium carbonate and
[0524] 50 ″ of water,
[0525] then grinding the mixture in a bead mill and atomizing and drying the suspension thus obtained in a spray tower by means of a one-phase nozzle.
C. BIOLOGICAL EXAMPLES
[0526] Trial Descriptions
[0527] In the tables below, the following abbreviations are used:
TABLE-US-00003 ABUTH: Abutilon theophrast AGSTE: Agrostis tenuis ALOMY: Alopecurus myosuroides AMARE: Amaranthus retroflexus AVEFA: Avena fatua DIGSA: Digitaria sanguinalis ECHCG: Echinochloa crus-galli HORMU: Hordeum murinum KCHSC: Kochia scoparia MATCH: Matricaria chamonilla LOLRI: Lolium rigidum POAAN: Poa annua MATIN: Matricaria inodora STEME: Stellaria media POLCO: Polygonum convolvulus SETVI: Setaria viridis VERPE: Veronica persica
[0528] Method A: Herbicidal Post-Emergence Action
[0529] Seeds of mono- and dicotyledonous weed plants are placed in plastic pots in sandy loam soil (twin sowing with one species each of mono- or dicotyledonous weed plants per pot), covered with soil and cultivated in a greenhouse under controlled growth conditions. 2 to 3 weeks after sowing, the test plants are treated at the one-leaf stage. The compounds of the invention, formulated in the form of wettable powders (WP) or as emulsion concentrates (EC), are applied to the green parts of the plants as aqueous suspension or emulsion with addition of 0.5% additive at a water application rate equivalent to 600 liters per hectare. After the test plants have been kept in the greenhouse under optimum growth conditions for about 3 weeks, the activity of the preparations is rated visually in comparison to untreated controls. For example, 100% activity=the plants have died, 0% activity=like control plants.
TABLE-US-00004 TABLE A1-1 Post-emergence action at 1280 g/ha against ALOMY Example Dosage number [g/ha] ALOMY I-503 1280 100 I-2853 1280 100 I-3597 1280 100 I-3858 1280 100 I-3850 1280 100 I-2171 1280 100 I-2912 1280 90 I-2205 1280 100 I-2176 1280 100 I-3101 1280 100 I-3861 1280 90 I-3136 1280 90 I-2601 1280 100 I-4376 1280 100 I-2869 1280 100 I-1957 1280 100 I-678 1280 90 I-502 1280 100 I-602 1280 100 I-610 1280 90 I-595 1280 100 I-575 1280 90 I-565 1280 100 I-570 1280 100 I-577 1280 100 I-1964 1280 100 I-3879 1280 100 I-2173 1280 100 I-584 1280 100 I-571 1280 100 I-551 1280 100 I-529 1280 100 I-612 1280 100 I-594 1280 100 I-554 1280 100 I-566 1280 100 I-600 1280 100 I-576 1280 100
TABLE-US-00005 TABLE A1-2 Post-emergence action at 320 g/ha against ALOMY Example Dosage number [g/ha] ALOMY I-577 320 100 I-554 320 100 I-565 320 100 I-594 320 90 I-3101 320 100 I-503 320 100 I-502 320 100 I-584 320 90 I-2176 320 100 I-2205 320 100 I-2853 320 100 I-602 320 100 I-570 320 100 I-576 320 100 I-3597 320 90 I-2173 320 100 I-2171 320 100 I-529 320 100 I-2601 320 100 I-571 320 100 I-2869 320 90 I-3850 320 90 I-610 320 90
TABLE-US-00006 TABLE A2-1 Post-emergence action at 1280 g/ha against DIGSA Example Dosage number [g/ha] DIGSA I-2853 1280 100 I-3101 1280 100 I-3136 1280 90 I-502 1280 100 I-565 1280 90 I-570 1280 100 I-2173 1280 100 I-584 1280 90 I-551 1280 90 I-594 1280 100 I-554 1280 100 I-566 1280 90 I-576 1280 90
TABLE-US-00007 TABLE A2-2 Post-emergence action at 320 g/ha against DIGSA Example Dosage number [g/ha] DIGSA I-554 320 100 I-565 320 90 I-3101 320 100 I-2853 320 100
TABLE-US-00008 TABLE A3-1 Post-emergence action at 1280 g/ha against ECHCG Example Dosage number [g/ha] ECHCG I-001 1280 100 I-2543 1280 100 I-2591 1280 90 I-1923 1280 100 I-507 1280 100 I-2059 1280 100 I-2596 1280 90 I-2583 1280 90 I-2562 1280 90 I-2549 1280 90 I-2550 1280 90 I-503 1280 100 I-504 1280 90 I-557 1280 90 I-2853 1280 100 I-3597 1280 100 I-3858 1280 100 I-2171 1280 100 I-2896 1280 90 I-2895 1280 90 I-2858 1280 90 I-2887 1280 90 I-2866 1280 90 I-2205 1280 100 I-2228 1280 90 I-2176 1280 100 I-3101 1280 100 I-3861 1280 90 I-3136 1280 90 I-3383 1280 90 I-2601 1280 90 I-2869 1280 90 I-1957 1280 90 I-656 1280 100 I-502 1280 100 I-602 1280 90 I-610 1280 100 I-595 1280 100 I-575 1280 90 I-565 1280 100 I-570 1280 90 I-577 1280 90 I-3879 1280 90 I-2173 1280 90 I-584 1280 100 I-497 1280 100 I-518 1280 90 I-516 1280 100 I-532 1280 100 I-510 1280 90 I-511 1280 100 I-513 1280 100 I-2791 1280 100 I-521 1280 90 I-551 1280 90 I-543 1280 90 I-501 1280 100 I-548 1280 90 I-527 1280 90 I-552 1280 100 I-525 1280 90 I-530 1280 90 I-559 1280 90 I-2605 1280 90 I-538 1280 100 I-535 1280 90 I-594 1280 100 I-554 1280 100 I-566 1280 100 I-600 1280 100
TABLE-US-00009 TABLE A3-2 Post-emergence action at 320 g/ha against ECHCG Example Dosage number [g/ha] ECHCG I-577 320 90 I-554 320 100 I-565 320 100 I-594 320 90 I-3101 320 100 I-503 320 100 I-502 320 100 I-584 320 100 I-2176 320 90 I-2205 320 100 I-2895 320 90 I-566 320 100 I-518 320 90 I-2059 320 100 I-516 320 90 I-595 320 100 I-532 320 100 I-2550 320 90 I-510 320 90 I-559 320 90 I-3597 320 100 I-501 320 100 I-2173 320 90 I-2171 320 100 I-535 320 90 I-538 320 100 I-2583 320 90 I-511 320 90 I-513 320 100 I-552 320 90 I-3879 320 90 I-507 320 90 I-2596 320 90 I-504 320 90 I-3858 320 100 I-2791 320 90 I-001 320 90
TABLE-US-00010 TABLE A4-1 Post-emergence action at 1280 g/ha against LOLRI Example Dosage number [g/ha] LOLRI I-2543 1280 100 I-1923 1280 100 I-2059 1280 100 I-2596 1280 90 I-2583 1280 100 I-2562 1280 100 I-2549 1280 100 I-2550 1280 100 I-503 1280 100 I-504 1280 90 I-2853 1280 100 I-3858 1280 90 I-2171 1280 90 I-2896 1280 100 I-2895 1280 100 I-2858 1280 100 I-2887 1280 100 I-2866 1280 90 I-2205 1280 100 I-2185 1280 90 I-2228 1280 90 I-2176 1280 100 I-3101 1280 100 I-3136 1280 100 I-2602 1280 90 I-4375 1280 90 I-4376 1280 100 I-2869 1280 90 I-1957 1280 100 I-502 1280 100 I-602 1280 100 I-610 1280 100 I-595 1280 90 I-565 1280 100 I-570 1280 100 I-577 1280 100 I-1964 1280 100 I-1967 1280 90 I-2173 1280 100 I-584 1280 100 I-571 1280 100 I-497 1280 100 I-518 1280 100 I-516 1280 90 I-532 1280 100 I-510 1280 90 I-511 1280 100 I-513 1280 100 I-500 1280 90 I-521 1280 100 I-551 1280 90 I-545 1280 90 I-543 1280 90 I-501 1280 100 I-527 1280 100 I-552 1280 90 I-528 1280 100 I-559 1280 100 I-539 1280 90 I-2605 1280 90 I-529 1280 90 I-538 1280 100 I-535 1280 100 I-612 1280 90 I-594 1280 100 I-554 1280 100 I-566 1280 100 I-600 1280 90 I-576 1280 100
TABLE-US-00011 TABLE A4-2 Post-emergence action at 320 g/ha against LOLRI Example Dosage number [g/ha] LOLRI I-577 320 100 I-554 320 100 I-565 320 100 I-594 320 100 I-3101 320 90 I-503 320 100 I-502 320 100 I-584 320 100 I-2205 320 90 I-2853 320 90 I-527 320 100 I-2895 320 90 I-566 320 100 I-518 320 90 I-602 320 90 I-2059 320 90 I-595 320 90 I-570 320 100 I-532 320 90 I-2550 320 100 I-510 320 90 I-559 320 90 I-576 320 100 I-501 320 100 I-535 320 90 I-2228 320 90 I-2562 320 90 I-543 320 90 I-528 320 90 I-511 320 90 I-2896 320 90 I-2858 320 90 I-2887 320 90 I-552 320 90 I-521 320 100
TABLE-US-00012 TABLE A5-1 Post-emergence action at 1280 g/ha against POANN Example Dosage number [g/ha] POAAN I-001 1280 100 I-2543 1280 100 I-2591 1280 100 I-1923 1280 100 I-506 1280 90 I-507 1280 100 I-2059 1280 100 I-2596 1280 100 I-2583 1280 100 I-2562 1280 100 I-2549 1280 100 I-2550 1280 100 I-503 1280 100 I-504 1280 100 I-557 1280 100 I-3845 1280 100 I-4341 1280 90 I-2853 1280 100 I-3597 1280 100 I-3858 1280 100 I-3850 1280 100 I-2171 1280 100 I-2912 1280 100 I-2896 1280 100 I-2895 1280 100 I-2858 1280 100 I-2887 1280 100 I-2866 1280 100 I-2867 1280 100 I-2205 1280 100 I-2185 1280 100 I-2228 1280 100 I-2176 1280 100 I-3101 1280 100 I-3861 1280 100 I-3136 1280 100 I-3383 1280 100 I-2602 1280 100 I-2601 1280 100 I-4375 1280 100 I-4376 1280 100 I-2869 1280 100 I-1957 1280 100 I-502 1280 100 I-602 1280 100 I-610 1280 100 I-595 1280 100 I-575 1280 100 I-565 1280 100 I-570 1280 100 I-577 1280 100 I-1964 1280 100 I-1944 1280 100 I-1967 1280 100 I-3879 1280 100 I-2173 1280 100 I-584 1280 100 I-571 1280 100 I-497 1280 100 I-546 1280 100 I-518 1280 100 I-516 1280 100 I-510 1280 100 I-511 1280 100 I-513 1280 100 I-2791 1280 100 I-500 1280 100 I-521 1280 100 I-551 1280 100 I-545 1280 100 I-543 1280 100 I-501 1280 100 I-544 1280 100 I-523 1280 100 I-548 1280 90 I-527 1280 100 I-552 1280 100 I-525 1280 100 I-530 1280 90 I-528 1280 100 I-526 1280 100 I-559 1280 100 I-539 1280 100 I-519 1280 100 I-2605 1280 100 I-2481 1280 100 I-529 1280 100 I-538 1280 100 I-535 1280 100 I-594 1280 100 I-554 1280 100 I-581 1280 100 I-566 1280 100 I-600 1280 100 I-576 1280 100
TABLE-US-00013 TABLE A5-2 Post-emergence action at 320 g/ha against POANN Example Dosage number [g/ha] POAAN I-577 320 100 I-554 320 100 I-565 320 100 I-594 320 90 I-3101 320 90 I-503 320 100 I-502 320 100 I-584 320 100 I-2176 320 100 I-2205 320 100 I-2853 320 100 I-527 320 100 I-2895 320 100 I-566 320 100 I-518 320 100 I-602 320 100 I-2059 320 100 I-516 320 100 I-595 320 100 I-570 320 100 I-532 320 100 I-2550 320 100 I-510 320 100 I-559 320 100 I-576 320 100 I-3597 320 100 I-501 320 100 I-2173 320 100 I-2171 320 100 I-535 320 100 I-2228 320 100 I-538 320 100 I-529 320 100 I-2602 320 100 I-2601 320 100 I-571 320 100 I-2583 320 100 I-2562 320 100 I-543 320 100 I-2869 320 100 I-528 320 100 I-513 320 100 I-3850 320 100 I-610 320 100 I-2896 320 100 I-2858 320 100 I-2887 320 100 I-552 320 100 I-500 320 100 I-521 320 100 I-2543 320 100 I-497 320 100 I-1923 320 100 I-507 320 90 I-2596 320 90 I-581 320 100 I-504 320 100 I-557 320 90 I-3845 320 100 I-3858 320 100 I-2912 320 100 I-2866 320 100 I-2867 320 100 I-2185 320 100 I-3136 320 100 I-3383 320 90 I-4376 320 100 I-519 320 100 I-545 320 100 I-2481 320 100 I-525 320 100 I-600 320 100 I-1967 320 100 I-2591 320 100 I-2549 320 100 I-4375 320 100 I-1957 320 100 I-1964 320 100 I-1944 320 100 I-546 320 100 I-551 320 100 I-530 320 90 I-526 320 100
TABLE-US-00014 TABLE A6 Post-emergence action at 1280 g/ha against SETVI Example Dosage number [g/ha] SETVI I-502 1280 90 I-595 1280 100 I-565 1280 90 I-551 1280 100
TABLE-US-00015 TABLE A7 Post-emergence action at 1280 g/ha against AMARE Example Dosage number [g/ha] AMARE I-2543 1280 100 I-610 1280 90 I-510 1280 100 I-500 1280 100 I-501 1280 100 I-527 1280 100 I-530 1280 90 I-528 1280 100
TABLE-US-00016 TABLE A8-1 Post-emergence action at 1280 g/ha against MATIN Example Dosage number [g/ha] MATIN I-001 1280 90 I-2543 1280 100 I-2059 1280 90 I-2596 1280 90 I-2583 1280 100 I-2562 1280 90 I-2549 1280 90 I-503 1280 100 I-504 1280 90 I-2853 1280 90 I-3858 1280 100 I-2171 1280 90 I-2896 1280 90 I-2205 1280 100 I-2228 1280 90 I-2176 1280 90 I-3101 1280 100 I-2602 1280 90 I-2869 1280 90 I-656 1280 90 I-502 1280 90 I-602 1280 90 I-610 1280 90 I-595 1280 90 I-565 1280 90 I-570 1280 90 I-577 1280 90 I-518 1280 90 I-516 1280 90 I-510 1280 90 I-511 1280 90 I-513 1280 90 I-2791 1280 90 I-500 1280 90 I-545 1280 90 I-501 1280 90 I-527 1280 90 I-552 1280 90 I-528 1280 90 I-539 1280 90 I-519 1280 90 I-538 1280 90 I-535 1280 90 I-594 1280 90 I-554 1280 90 I-566 1280 90 I-576 1280 90
TABLE-US-00017 TABLE A8-2 Post-emergence action at 320 g/ha against MATIN Example Dosage number [g/ha] MATIN I-577 320 90 I-503 320 100 I-2602 320 90 I-2583 320 100 I-2562 320 90 I-500 320 90
TABLE-US-00018 TABLE A9-1 Post-emergence action at 1280 g/ha against STEME Example Dosage number [g/ha] STEME I-001 1280 100 I-2543 1280 100 I-2591 1280 100 I-1923 1280 100 I-506 1280 90 I-507 1280 90 I-2059 1280 100 I-2596 1280 100 I-2562 1280 90 I-2549 1280 100 I-2550 1280 100 I-503 1280 100 I-557 1280 100 I-3845 1280 100 I-4341 1280 100 I-2853 1280 100 I-3597 1280 100 I-3858 1280 90 I-3850 1280 100 I-2171 1280 100 I-2912 1280 100 I-2896 1280 100 I-2895 1280 100 I-2858 1280 100 I-2887 1280 100 I-2866 1280 100 I-2867 1280 100 I-2205 1280 100 I-2185 1280 100 I-2228 1280 100 I-2176 1280 100 I-3101 1280 100 I-3136 1280 100 I-3383 1280 100 I-2602 1280 100 I-2601 1280 100 I-4375 1280 90 I-4376 1280 100 I-2869 1280 100 I-1957 1280 100 I-626 1280 100 I-656 1280 90 I-502 1280 100 I-602 1280 100 I-610 1280 100 I-595 1280 100 I-565 1280 100 I-570 1280 100 I-577 1280 100 I-1964 1280 100 I-1944 1280 100 I-1967 1280 100 I-3879 1280 100 I-2173 1280 100 I-584 1280 100 I-571 1280 100 I-497 1280 100 I-546 1280 100 I-518 1280 100 I-516 1280 100 I-532 1280 100 I-510 1280 100 I-511 1280 100 I-513 1280 100 I-2791 1280 100 I-500 1280 100 I-521 1280 100 I-551 1280 100 I-545 1280 100 I-543 1280 100 I-501 1280 100 I-544 1280 90 I-523 1280 100 I-527 1280 100 I-552 1280 100 I-525 1280 100 I-530 1280 90 I-528 1280 100 I-526 1280 100 I-559 1280 100 I-539 1280 90 I-519 1280 100 I-2605 1280 90 I-2481 1280 100 I-529 1280 100 I-538 1280 100 I-535 1280 100 I-612 1280 100 I-594 1280 100 I-554 1280 100 I-581 1280 100 I-566 1280 100 I-601 1280 100 I-600 1280 100 I-576 1280 100
TABLE-US-00019 TABLE A9-2 Post-emergence action at 320 g/ha against STEME Example Dosage number [g/ha] STEME I-577 320 100 I-554 320 100 I-565 320 100 I-594 320 100 I-3101 320 100 I-503 320 100 I-502 320 100 I-584 320 100 I-2176 320 100 I-2205 320 100 I-2853 320 100 I-527 320 100 I-2895 320 90 I-566 320 100 I-518 320 100 I-602 320 100 I-2059 320 100 I-516 320 90 I-595 320 100 I-570 320 100 I-532 320 90 I-2550 320 90 I-510 320 100 I-559 320 90 I-576 320 100 I-3597 320 100 I-501 320 100 I-2173 320 100 I-2171 320 100 I-535 320 100 I-2228 320 100 I-538 320 100 I-529 320 100 I-2602 320 90 I-2601 320 90 I-571 320 90 I-543 320 100 I-2869 320 90 I-528 320 100 I-511 320 90 I-513 320 100 I-3850 320 100 I-610 320 100 I-2896 320 100 I-2858 320 100 I-2887 320 100 I-500 320 100 I-521 320 100 I-3879 320 100 I-2543 320 100 I-497 320 100 I-1923 320 90 I-581 320 100 I-557 320 100 I-3845 320 100 I-2912 320 100 I-2866 320 100 I-2867 320 100 I-2185 320 100 I-3136 320 100 I-3383 320 100 I-2791 320 100 I-4376 320 90 I-519 320 100 I-545 320 100 I-2481 320 100 I-525 320 90 I-600 320 100 I-1967 320 100 I-626 320 100 I-656 320 90 I-523 320 100 I-612 320 100 I-601 320 100
TABLE-US-00020 TABLE A10 Post-emergence action at 1280 g/ha against VERPE Example Dosage number [g/ha] VERPE I-2912 1280 90 I-2176 1280 90 I-3861 1280 90 I-610 1280 90
TABLE-US-00021 TABLE A11 Post-emergence action at 1280 g/ha against ABUTH Example Dosage number [g/ha] ABUTH I-2583 1280 90 I-516 1280 100 I-528 1280 90 I-566 1280 100
[0530] As the results show, inventive compounds such as, for example, compound nos. I-502, I-1964, I-554, 1-3101, I-656, I-538, I-2549, I-559, I-2550, I-503, I-502, I-595, I-2543, I-500, I-3101, I-001, I-602, I-4341, I-3861, I-610, I-2583, I-516 and other compounds from tables A1-A11 show good herbicidal efficacy against harmful plants in the case of post-emergence treatment. For example, compounds I-502 and I-1964 in the post-emergence method have very good herbicidal action (80% to 100% herbicidal action) against harmful plants such as Alopecurus myosuroides, I-656 and I-538 against Echinochloa crus-galli, I-2549 and I-559 against Lolium rigidum, I-3101 and I-001 against Matricaria inodora, I-2550 and I-503 against Poa annua and I-602 and I-4341 against Stellaria media, and compounds I-554 and I-3101 in the post-emergence method have very good herbicidal action (80% 100% herbicidal action) against harmful plants such as Digitaria sanguinalis, I-502 and I-595 against Setaria viridis, I-2543 and I-500 against Amaranthus retroflexus at an application rate of 1.28 kg of active substance or less per hectare.
[0531] Method B: Herbicidal Pre-Emergence Action
[0532] Seeds of mono- and dicotyledonous weed plants are placed in plastic pots in sandy loam soil (doubly sown with one species each of mono- or dicotyledonous weed plants per pot) and covered with soil. The compounds of the invention, formulated in the form of wettable powders (WP) or as emulsion concentrates (EC), are then applied onto the surface of the covering soil as aqueous suspension or emulsion with addition of 0.5% additive at a water application rate equivalent to 600 liters per hectare. After the treatment, the pots are placed in a greenhouse and kept under good growth conditions for the trial plants. After about 3 weeks, the effect of the preparations is scored visually in comparison with untreated controls as percentages. For example, 100% action=the plants have died, 0% action=like control plants.
TABLE-US-00022 TABLE B1-1 Pre-emergence action at 1280 g/ha against ALOMY Example Dosage number [g/ha] ALOMY I-503 1280 90 I-4341 1280 90 I-2853 1280 100 I-3858 1280 100 I-2171 1280 90 I-2205 1280 100 I-2185 1280 100 I-2176 1280 90 I-3101 1280 100 I-502 1280 100 I-602 1280 100 I-610 1280 90 I-595 1280 90 I-575 1280 90 I-565 1280 90 I-570 1280 100 I-577 1280 90 I-1964 1280 90 I-1967 1280 90 I-2173 1280 90 I-571 1280 90 I-551 1280 100 I-594 1280 100 I-554 1280 90 I-566 1280 90 I-600 1280 90 I-576 1280 90
TABLE-US-00023 TABLE BI-2 Pre-emergence action at 320 g/ha against ALOMY Example Dosage number [g/ha] ALOMY I-554 320 90 I-2173 320 90 I-594 320 90 I-502 320 90 I-2853 320 90 I-610 320 90 I-570 320 100
TABLE-US-00024 TABLE B2-1 Pre-emergence action at 1280 g/ha against DIGSA Example Dosage number [g/ha] DIGSA I-503 1280 90 I-2853 1280 100 I-3597 1280 90 I-3858 1280 100 I-3850 1280 90 I-2171 1280 90 I-2205 1280 90 I-2176 1280 90 I-3101 1280 90 I-3861 1280 90 I-3136 1280 90 I-1957 1280 90 I-678 1280 90 I-502 1280 100 I-602 1280 90 I-610 1280 90 I-595 1280 90 I-575 1280 90 I-565 1280 90 I-577 1280 100 I-1964 1280 90 I-3879 1280 90 I-2173 1280 90 I-584 1280 90 I-571 1280 90 I-551 1280 90 I-529 1280 90 I-594 1280 90 I-554 1280 100 I-581 1280 90 I-566 1280 90 I-600 1280 90 I-576 1280 100
TABLE-US-00025 TABLE B2-2 Pre-emergence action at 320 g/ha against DIGSA Example Dosage number [g/ha] DIGSA I-2173 320 90 I-594 320 90 I-502 320 90 I-3858 320 90 I-576 320 100 I-566 320 90 I-503 320 90 I-529 320 90 I-577 320 90
TABLE-US-00026 TABLE B3-1 Pre-emergence action at 1280 g/ha against ECHCG Example Dosage number [g/ha] EGHCG I-001 1280 90 I-2543 1280 100 I-2591 1280 100 I-1923 1280 100 I-506 1280 100 I-507 1280 100 I-2059 1280 100 I-2596 1280 100 I-2583 1280 100 I-2562 1280 100 I-2549 1280 100 I-2550 1280 100 I-503 1280 100 I-504 1280 100 I-557 1280 90 I-3845 1280 100 I-4341 1280 100 I-2853 1280 100 I-3597 1280 90 I-3858 1280 100 I-3850 1280 100 I-2896 1280 100 I-2895 1280 100 I-2858 1280 90 I-2866 1280 100 I-2867 1280 100 I-2205 1280 100 I-2185 1280 100 I-2228 1280 100 I-2176 1280 90 I-3101 1280 100 I-3861 1280 100 I-3136 1280 100 I-3383 1280 100 I-2601 1280 90 I-4376 1280 90 I-2869 1280 100 I-1957 1280 100 I-626 1280 100 I-678 1280 100 I-656 1280 100 I-502 1280 100 I-602 1280 90 I-610 1280 90 I-595 1280 100 I-575 1280 90 I-565 1280 90 I-570 1280 90 I-577 1280 100 I-1964 1280 90 I-1967 1280 90 I-3879 1280 90 I-2173 1280 90 I-584 1280 90 I-571 1280 90 I-497 1280 100 I-546 1280 100 I-518 1280 100 I-516 1280 100 I-532 1280 100 I-510 1280 100 I-511 1280 100 I-513 1280 100 I-2791 1280 100 I-500 1280 100 I-521 1280 100 I-551 1280 100 I-545 1280 90 I-543 1280 100 I-501 1280 100 I-544 1280 100 I-523 1280 90 I-548 1280 100 I-527 1280 100 I-552 1280 90 I-525 1280 90 I-528 1280 90 I-559 1280 100 I-539 1280 90 I-519 1280 90 I-2605 1280 90 I-2481 1280 100 I-529 1280 90 I-538 1280 100 I-535 1280 100 I-612 1280 100 I-594 1280 100 I-554 1280 90 I-600 1280 90 I-576 1280 90
TABLE-US-00027 TABLE B3-2 Pre-emergence action at 320 g/ha against ECHCG Example Dosage number [g/ha] EGHCG I-554 320 90 I-2173 320 90 I-497 320 100 I-594 320 100 I-502 320 100 I-3858 320 100 I-3845 320 100 I-501 320 100 I-538 320 90 I-535 320 100 I-532 320 100 I-2895 320 100 I-510 320 100 I-511 320 100 I-610 320 90 I-503 320 100 I-504 320 90 I-559 320 90 I-2543 320 100 I-2228 320 90 I-1923 320 100 I-2176 320 90 I-3101 320 100 I-2059 320 100 I-2596 320 100 I-2583 320 100 I-2562 320 100 I-2549 320 100 I-2550 320 90 I-500 320 90 I-529 320 90 I-551 320 100 I-571 320 90 I-527 320 90 I-2896 320 100 I-518 320 90 I-543 320 100 I-2205 320 100 I-548 320 90 I-3861 320 90 I-546 320 100 I-3383 320 100 I-2791 320 100 I-1957 320 90 I-678 320 100 I-656 320 90 I-626 320 90 I-3850 320 90 I-577 320 90 I-2481 320 90 I-612 320 90 I-602 320 90 I-2185 320 90 I-3136 320 90 I-565 320 90
TABLE-US-00028 TABLE B4-1 Pre-emergence action at 1280 g/ha against LOLRI Example Dosage number [g/ha] LOLRI I-2543 1280 100 I-2591 1280 100 I-1923 1280 100 I-506 1280 100 I-507 1280 90 I-2059 1280 100 I-2596 1280 100 I-2583 1280 100 I-2562 1280 90 I-2549 1280 100 I-2550 1280 90 I-503 1280 100 I-504 1280 90 I-557 1280 100 I-3845 1280 90 I-4341 1280 90 I-2853 1280 100 I-3597 1280 90 I-3858 1280 100 I-3850 1280 100 I-2171 1280 100 I-2896 1280 100 I-2895 1280 100 I-2858 1280 100 I-2887 1280 90 I-2866 1280 100 I-2867 1280 100 I-2185 1280 90 I-2228 1280 100 I-2176 1280 100 I-3101 1280 100 I-3861 1280 90 I-3136 1280 90 I-3383 1280 90 I-2601 1280 90 I-4375 1280 90 I-4376 1280 90 I-2869 1280 100 I-1957 1280 90 I-626 1280 90 I-678 1280 100 I-656 1280 90 I-502 1280 100 I-602 1280 100 I-610 1280 100 I-595 1280 100 I-575 1280 100 I-565 1280 90 I-570 1280 100 I-577 1280 90 I-1964 1280 100 I-1944 1280 90 I-1967 1280 100 I-3879 1280 90 I-2173 1280 100 I-584 1280 100 I-571 1280 90 I-497 1280 100 I-546 1280 90 I-518 1280 100 I-516 1280 100 I-532 1280 100 I-510 1280 100 I-511 1280 100 I-513 1280 90 I-2791 1280 90 I-500 1280 100 I-521 1280 100 I-551 1280 100 I-545 1280 100 I-543 1280 100 I-501 1280 100 I-544 1280 90 I-523 1280 100 I-548 1280 90 I-527 1280 100 I-552 1280 90 I-525 1280 100 I-530 1280 90 I-528 1280 100 I-526 1280 100 I-559 1280 100 I-539 1280 90 I-519 1280 100 I-2605 1280 100 I-2481 1280 90 I-529 1280 100 I-538 1280 90 I-535 1280 100 I-612 1280 90 I-594 1280 90 I-554 1280 100 I-581 1280 90 I-566 1280 90 I-601 1280 90 I-600 1280 100 I-576 1280 90
TABLE-US-00029 TABLE B4-2 Pre-emergence action at 320 g/ha against LOLRI Example Dosage number [g/ha] LOLRI I-554 320 100 I-2173 320 90 I-497 320 90 I-594 320 90 I-502 320 100 I-3858 320 90 I-3845 320 90 I-501 320 100 I-2853 320 90 I-576 320 90 I-538 320 90 I-535 320 100 I-566 320 90 I-532 320 100 I-2895 320 100 I-510 320 100 I-511 320 100 I-610 320 100 I-503 320 90 I-504 320 90 I-559 320 100 I-552 320 90 I-2543 320 100 I-2228 320 90 I-1923 320 90 I-2176 320 90 I-3101 320 100 I-2059 320 100 I-2596 320 100 I-2583 320 90 I-2562 320 90 I-2549 320 100 I-2550 320 90 I-2605 320 90 I-500 320 90 I-529 320 100 I-551 320 90 I-571 320 90 I-527 320 90 I-2896 320 100 I-2858 320 100 I-570 320 90 I-518 320 100 I-543 320 100 I-575 320 90 I-523 320 90 I-506 320 90 I-557 320 90 I-1964 320 90 I-525 320 90 I-1967 320 90 I-2887 320 90 I-2866 320 100 I-2867 320 100 I-584 320 100 I-516 320 100 I-521 320 90 I-2869 320 90 I-528 320 90 I-678 320 90 I-519 320 90 I-595 320 90 I-600 320 90
TABLE-US-00030 TABLE B5-1 Pre-emergence action at 1280 g/ha against POAAN Example Dosage number [g/ha] POANN I-001 1280 100 I-2543 1280 100 I-2591 1280 100 I-1923 1280 100 I-506 1280 100 I-507 1280 100 I-2059 1280 100 I-2596 1280 100 I-2583 1280 100 I-2562 1280 100 I-2549 1280 100 I-2550 1280 100 I-503 1280 100 I-504 1280 100 I-557 1280 100 I-3845 1280 100 I-4341 1280 90 I-2853 1280 100 I-3597 1280 100 I-3858 1280 100 I-3850 1280 100 I-2171 1280 100 I-2912 1280 90 I-2896 1280 100 I-2895 1280 100 I-2858 1280 100 I-2887 1280 100 I-2866 1280 100 I-2867 1280 100 I-2205 1280 100 I-2185 1280 100 I-2228 1280 100 I-2176 1280 100 I-3101 1280 100 I-3861 1280 100 I-3136 1280 100 I-3383 1280 100 I-2602 1280 100 I-2601 1280 90 I-4375 1280 100 I-4376 1280 100 I-2869 1280 100 I-1957 1280 100 I-626 1280 90 I-678 1280 90 I-656 1280 100 I-502 1280 100 I-602 1280 100 I-610 1280 100 I-595 1280 100 I-575 1280 100 I-565 1280 100 I-570 1280 100 I-577 1280 100 I-1964 1280 100 I-1944 1280 100 I-1967 1280 100 I-3879 1280 100 I-2173 1280 100 I-584 1280 100 I-571 1280 100 I-497 1280 100 I-546 1280 100 I-518 1280 100 I-516 1280 100 I-532 1280 100 I-510 1280 100 I-511 1280 100 I-513 1280 100 I-2791 1280 100 I-500 1280 100 I-521 1280 100 I-551 1280 100 I-545 1280 100 I-543 1280 100 I-501 1280 100 I-544 1280 100 I-523 1280 100 I-548 1280 100 I-527 1280 100 I-552 1280 100 I-525 1280 100 I-530 1280 100 I-528 1280 100 I-526 1280 100 I-559 1280 100 I-539 1280 100 I-519 1280 100 I-2605 1280 100 I-2481 1280 100 I-529 1280 100 I-538 1280 100 I-535 1280 100 I-612 1280 90 I-594 1280 100 I-554 1280 100 I-581 1280 100 I-566 1280 100 I-601 1280 100 I-600 1280 90 I-576 1280 100
TABLE-US-00031 TABLE B5-2 Pre-emergence action at 320 g/ha against POAAN Example Dosage number [g/ha] POAAN I-554 320 100 I-2173 320 100 I-497 320 100 I-594 320 100 I-502 320 90 I-3858 320 100 I-3845 320 100 I-501 320 100 I-2853 320 100 I-576 320 100 I-538 320 100 I-535 320 100 I-566 320 100 I-532 320 100 I-2895 320 100 I-510 320 100 I-511 320 100 I-610 320 100 I-503 320 100 I-504 320 100 I-559 320 100 I-552 320 100 I-2543 320 100 I-2228 320 100 I-1923 320 100 I-2176 320 100 I-3101 320 100 I-2059 320 100 I-2596 320 100 I-2583 320 100 I-2562 320 100 I-2549 320 100 I-2550 320 100 I-2605 320 90 I-500 320 100 I-551 320 90 I-571 320 90 I-527 320 100 I-2896 320 100 I-2858 320 100 I-570 320 100 I-518 320 100 I-543 320 100 I-2205 320 100 I-575 320 100 I-523 320 100 I-506 320 100 I-548 320 100 I-557 320 100 I-1964 320 90 I-525 320 100 I-1967 320 100 I-601 320 100 I-2887 320 100 I-2866 320 100 I-2867 320 100 I-584 320 100 I-3861 320 100 I-546 320 100 I-3383 320 100 I-516 320 100 I-513 320 100 I-2791 320 90 I-521 320 100 I-2869 320 90 I-1957 320 90 I-528 320 100 I-656 320 100 I-519 320 90 I-595 320 100 I-2591 320 100 I-526 320 100 I-539 320 100 I-2912 320 90 I-1944 320 90 I-545 320 100 I-4375 320 100 I-507 320 90 I-544 320 100 I-581 320 90
TABLE-US-00032 TABLE B6 Pre-emergence action at 1280 g/ha against SETVI Example Dosage number [g/ha] SETVI I-2543 1280 90 I-506 1280 90 I-2583 1280 90 I-2562 1280 90 I-503 1280 90 I-504 1280 90 I-3845 1280 90 I-2853 1280 100 I-3858 1280 90 I-2896 1280 100 I-2228 1280 100 I-3101 1280 90 I-3136 1280 100 I-502 1280 90 I-610 1280 90 I-570 1280 100 I-577 1280 100 I-1944 1280 90 I-584 1280 90 I-571 1280 90 I-497 1280 90 I-546 1280 90 I-532 1280 100 I-510 1280 90 I-511 1280 100 I-551 1280 90 I-545 1280 90 I-543 1280 90 I-528 1280 100 I-538 1280 90 I-535 1280 90 I-594 1280 90 I-554 1280 90 I-566 1280 90 I-600 1280 90 I-576 1280 90
TABLE-US-00033 TABLE B7 Pre-emergence action at 1280 g/ha against ABUTH Example Dosage number [g/ha] ABUTH I-2583 1280 90 I-2549 1280 90 I-3858 1280 90 I-2887 1280 90 I-2205 1280 90 I-2228 1280 90 I-4375 1280 90 I-626 1280 90 I-602 1280 90 I-610 1280 90 I-2173 1280 90 I-571 1280 90 I-521 1280 100 I-551 1280 90 I-527 1280 90 I-552 1280 90 I-528 1280 90 I-535 1280 90 I-594 1280 90
TABLE-US-00034 TABLE B8 Pre-emergence action at 1280 g/ha against AMARE Example Dosage number [g/ha] AMARE I-2896 1280 100 I-2858 1280 90 I-2887 1280 100 I-2205 1280 90 I-2228 1280 90 I-4375 1280 90 I-626 1280 90 I-1967 1280 90 I-521 1280 100 I-528 1280 100 I-535 1280 90
TABLE-US-00035 TABLE B9 Pre-emergence action at 1280 g/ha against KCHSC Example Dosage number [g/ha] KCHSC I-3597 1280 90 I-2205 1280 90 I-1957 1280 90 I-577 1280 90
TABLE-US-00036 TABLE B10-1 Pre-emergence action at 1280 g/ha against MATIN Example Dosage number [g/ha] MATIN I-001 1280 100 I-2543 1280 100 I-2591 1280 90 I-1923 1280 100 I-506 1280 100 I-507 1280 90 I-2059 1280 100 I-2596 1280 90 I-2583 1280 100 I-2562 1280 100 I-503 1280 100 I-504 1280 100 I-3845 1280 100 I-4341 1280 90 I-2853 1280 100 I-3597 1280 100 I-3858 1280 100 I-3850 1280 90 I-2171 1280 100 I-2896 1280 100 I-2895 1280 100 I-2858 1280 100 I-2887 1280 100 I-2866 1280 90 I-2867 1280 90 I-2205 1280 100 I-2228 1280 100 I-2176 1280 90 I-3101 1280 100 I-3136 1280 90 I-3383 1280 100 I-4375 1280 100 I-1957 1280 90 I-626 1280 90 I-678 1280 90 I-656 1280 90 I-502 1280 100 I-610 1280 90 I-595 1280 90 I-565 1280 100 I-570 1280 100 I-577 1280 100 I-1964 1280 100 I-1967 1280 100 I-3879 1280 90 I-2173 1280 100 I-584 1280 90 I-571 1280 100 I-497 1280 100 I-546 1280 100 I-518 1280 100 I-516 1280 100 I-532 1280 100 I-510 1280 100 I-511 1280 100 I-513 1280 100 I-2791 1280 90 I-500 1280 100 I-543 1280 100 I-501 1280 100 I-552 1280 100 I-525 1280 100 I-528 1280 100 I-559 1280 100 I-539 1280 100 I-519 1280 90 I-2605 1280 100 I-2481 1280 90 I-538 1280 100 I-535 1280 100 I-594 1280 100 I-554 1280 100 I-581 1280 100 I-566 1280 100 I-601 1280 100 I-576 1280 100
TABLE-US-00037 TABLE B10-2 Pre-emergence action at 320 g/ha against MATIN Example Dosage number [g/ha] MATIN I-554 320 90 I-2173 320 90 I-497 320 100 I-3858 320 90 I-3845 320 90 I-501 320 100 I-2853 320 90 I-576 320 100 I-538 320 100 I-535 320 100 I-566 320 90 I-532 320 100 I-2895 320 90 I-510 320 100 I-511 320 100 I-504 320 100 I-559 320 100 I-552 320 90 I-2605 320 100 I-2858 320 90 I-2205 320 90 I-601 320 90
TABLE-US-00038 TABLE B11-1 Pre-emergence action at 1280 g/ha against STEME Example Dosage number [g/ha] STEME I-001 1280 100 I-2543 1280 100 I-2591 1280 100 I-1923 1280 100 I-506 1280 100 I-507 1280 90 I-2059 1280 100 I-2596 1280 100 I-2583 1280 100 I-2562 1280 100 I-2549 1280 100 I-2550 1280 100 I-503 1280 100 I-504 1280 100 I-557 1280 100 I-3845 1280 100 I-4341 1280 100 I-2853 1280 100 I-3597 1280 100 I-3858 1280 100 I-3850 1280 100 I-2171 1280 100 I-2912 1280 100 I-2896 1280 100 I-2895 1280 100 I-2858 1280 100 I-2887 1280 100 I-2866 1280 100 I-2867 1280 100 I-2205 1280 100 I-2185 1280 100 I-2228 1280 100 I-2176 1280 100 I-3101 1280 100 I-3861 1280 100 I-3136 1280 100 I-3383 1280 100 I-2602 1280 100 I-2601 1280 100 I-4375 1280 100 I-4376 1280 100 I-2869 1280 100 I-1957 1280 100 I-626 1280 100 I-678 1280 100 I-656 1280 100 I-502 1280 100 I-602 1280 100 I-610 1280 100 I-595 1280 100 I-575 1280 100 I-565 1280 100 I-570 1280 100 I-577 1280 100 I-1964 1280 100 I-1944 1280 90 I-1967 1280 100 I-3879 1280 100 I-2173 1280 100 I-584 1280 100 I-571 1280 100 I-497 1280 100 I-546 1280 100 I-518 1280 100 I-516 1280 100 I-532 1280 100 I-510 1280 100 I-511 1280 100 I-513 1280 100 I-2791 1280 100 I-500 1280 100 I-521 1280 100 I-551 1280 100 I-545 1280 100 I-543 1280 100 I-501 1280 100 I-544 1280 100 I-523 1280 100 I-548 1280 100 I-527 1280 100 I-552 1280 100 I-525 1280 100 I-530 1280 90 I-528 1280 100 I-526 1280 100 I-559 1280 100 I-539 1280 100 I-519 1280 100 I-2605 1280 100 I-2481 1280 100 I-529 1280 100 I-538 1280 100 I-535 1280 100 I-612 1280 100 I-594 1280 100 I-554 1280 100 I-581 1280 90 I-566 1280 100 I-601 1280 100 I-600 1280 100 I-576 1280 100
TABLE-US-00039 TABLE B11-2 Pre-emergence action at 320 g/ha against STEME Example Dosage number [g/ha] STEME I-554 320 100 I-2173 320 100 I-497 320 100 I-594 320 100 I-502 320 100 I-3858 320 100 I-3845 320 100 I-501 320 100 I-2853 320 100 I-576 320 100 I-538 320 100 I-535 320 100 I-566 320 100 I-532 320 100 I-2895 320 100 I-510 320 100 I-511 320 100 I-610 320 100 I-503 320 100 I-504 320 100 I-559 320 100 I-552 320 100 I-2543 320 100 I-2228 320 100 I-1923 320 100 I-2176 320 100 I-3101 320 100 I-2059 320 100 I-2596 320 100 I-2583 320 100 I-2562 320 100 I-2549 320 100 I-2550 320 100 I-2605 320 100 I-500 320 100 I-529 320 100 I-551 320 100 I-571 320 100 I-527 320 100 I-2896 320 100 I-2858 320 100 I-570 320 100 I-518 320 100 I-543 320 100 I-2205 320 90 I-575 320 100 I-523 320 100 I-506 320 100 I-548 320 100 I-557 320 100 I-1964 320 100 I-525 320 100 I-1967 320 100 I-601 320 100 I-2887 320 100 I-2866 320 100 I-2867 320 100 I-584 320 100 I-3861 320 100 I-546 320 100 I-3383 320 100 I-516 320 100 I-513 320 100 I-2791 320 100 I-521 320 100 I-2869 320 100 I-1957 320 100 I-528 320 100 I-678 320 100 I-656 320 100 I-519 320 100 I-595 320 100 I-600 320 100 I-2591 320 100 I-626 320 100 I-526 320 90 I-539 320 100 I-3850 320 90 I-2912 320 90 I-1944 320 90 I-2481 320 90 I-545 320 100 I-612 320 100 I-4375 320 100 I-001 320 100 I-4341 320 90
TABLE-US-00040 TABLE B12 Pre-emergence action at 1280 g/ha against VERPE Example Dosage number [g/ha] VERPE I-4341 1280 90 I-2171 1280 100
[0533] As the results show, inventive compounds such as, for example, compounds I-3101, I-502, I-577, I-3858, I-1923, I-506, I-3101, I-570, I-2171, I-507, I-2896, I-2228, I-2173, I-571, I-521, I-528, I-1957, I-3597, I-497, I-2185, I-2228, I-4341, I-2171 and other compounds from tables B1-B12 show good herbicidal efficacy against harmful plants in the case of post-emergence treatment. For example, compounds I-2173 and I-571 in the pre-emergence method have very good herbicidal action (80% to 100% herbicidal action) against harmful plants such as Abutilon theophrast, I-1923 and I-506 against Echinochloa crus-galli, I-3101 and I-570 against Lolium rigidum, I-2171 and I-507 against Poa annua and I-2185 and I-2228 against Stellaria media, at an application rate of 1.28 kg of active substance or less per hectare.
[0534] Method C Herbicidal Early Post-Emergence Action
[0535] Seeds of monocotyledonous or dicotyledonous weed plants are placed in 96-well microtiter plates in quartz sand and grown in a climatized chamber under controlled growth conditions. 5 to 7 days after sowing, the test plants are treated at the cotyledon stage. The compounds of the invention, formulated in the form of emulsion concentrates (EC), are applied with a water application rate of the equivalent of 2200 liters per hectare. After the test plants had been left to stand in the climatized chamber for 9 to 12 days under optimum growth conditions, the effect of the preparations is scored visually in comparison to untreated controls. For example, 100% activity=the plants have died, 0% activity=like control plants.
TABLE-US-00041 TABLE C1 Early post-emergence action at 1280 g/ha against AGSTE Example Dosage number [g/ha] AGSTE I-614 1900 100 I-578 1900 100 I-583 1900 100 I-564 1900 100 I-561 1900 100 I-536 1900 100 I-591 1900 100 I-562 1900 100 I-569 1900 100 I-568 1900 100 I-567 1900 100
TABLE-US-00042 TABLE C2 Early post-emergence action at 1280 g/ha against LOLPE Example Dosage number [g/ha] LOLPE I-1968 1900 100 I-614 1900 100 I-578 1900 100 I-591 1900 100 I-569 1900 100 I-567 1900 100
TABLE-US-00043 TABLE C3 Early post-emergence action at 1280 g/ha against POAAN Example Dosage number [g/ha] POAAN I-1959 1900 100 I-1968 1900 100 I-614 1900 100 I-578 1900 100 I-583 1900 100 I-564 1900 100 I-561 1900 100 I-536 1900 100 I-2977 1900 80 I-512 1900 80 I-591 1900 100 I-562 1900 100 I-569 1900 100 I-568 1900 100 I-567 1900 100
TABLE-US-00044 TABLE C4 Early post-emergence action at 1280 g/ha against MATCH Example Dosage number [g/ha] MATCH I-614 1900 100 I-578 1900 80 I-583 1900 100 I-564 1900 100 I-536 1900 100 I-2977 1900 80 I-562 1900 100 I-569 1900 100 I-568 1900 100 I-567 1900 80
TABLE-US-00045 TABLE C5 Early post-emergence action at 1280 g/ha against STEME Example Dosage number [g/ha] STEME I-614 1900 100 I-578 1900 100 I-583 1900 100 I-564 1900 100 I-2667 1900 100 I-536 1900 100 I-591 1900 80 I-562 1900 80 I-569 1900 80 I-568 1900 100 I-567 1900 80
[0536] As the results show, compounds of the invention, for example compounds I-568, I-567, I-569, I-591, 1-1968, I-614, I-564, I-536, I-2667 and I-536 and other compounds from tables C1-C5, in the early post-emergence method, show very good herbicidal action against harmful plants such as Agrostis capillaris, Echinochloa crus-galli, Lolium perenne, Matricaria chamomilla, Poa annua and Stellaria media, at an application rate of 1900 g of active substance or less per hectare. For example, compounds I-568 and I-567 in the early post-emergence method have very good herbicidal action (80% to 100% herbicidal action) against harmful plants such as Agrostis tenuis, I-569 and I-591 against Lolium rigidum, I-1968 and I-614 against Poa annua, I-564 and I-536 against Matricaria inodora, and I-2667 and I-536 against Stellaria media, at an application rate of 1.28 kg of active substance or less per hectare.
TABLE-US-LTS-00001 LENGTHY TABLES The patent application contains a lengthy table section. A copy of the table is available in electronic form from the USPTO web site (). An electronic copy of the table will also be available from the USPTO upon request and payment of the fee set forth in 37 CFR 1.19(b)(3).