Herbicidal pyrimidine compounds
11178871 · 2021-11-23
Assignee
Inventors
- Florian Vogt (Ludwigshafen, DE)
- Matthias Witschel (Ludwigshafen, DE)
- Tobias Seiser (Limburgerhof, DE)
- Veronica Lopez Carrillo (Ludwigshafen, DE)
- Thomas Seitz (Ludwigshafen, DE)
- Gerd Kraemer (Limburgerhof, DE)
- Klaus Kreuz (Limburgerhof, DE)
- Trevor William Newton (Limburgerhof, DE)
- Klaus Reinhard (Limburgerhof, DE)
- Doreen Schachtschabel (Limburgerhof, DE)
Cpc classification
C07D413/04
CHEMISTRY; METALLURGY
C07D405/06
CHEMISTRY; METALLURGY
A01N43/82
HUMAN NECESSITIES
C07D239/26
CHEMISTRY; METALLURGY
C07D409/04
CHEMISTRY; METALLURGY
C07D405/04
CHEMISTRY; METALLURGY
A01N43/80
HUMAN NECESSITIES
C07D403/04
CHEMISTRY; METALLURGY
C07D413/06
CHEMISTRY; METALLURGY
C07D417/04
CHEMISTRY; METALLURGY
International classification
C07D403/04
CHEMISTRY; METALLURGY
A01N43/82
HUMAN NECESSITIES
A01N43/80
HUMAN NECESSITIES
C07D405/04
CHEMISTRY; METALLURGY
C07D413/06
CHEMISTRY; METALLURGY
C07D413/04
CHEMISTRY; METALLURGY
C07D417/04
CHEMISTRY; METALLURGY
C07D239/26
CHEMISTRY; METALLURGY
C07D409/04
CHEMISTRY; METALLURGY
Abstract
The present invention relates to the use of pyrimidine compounds of formula (I), ##STR00001## or their agriculturally acceptable salts or derivatives as herbicides, wherein the variables are defined according to the description, specific pyrimidine compounds of formula (I), compositions comprising them and their use as herbicides, i.e. for controlling harmful plants, and also a method for controlling unwanted vegetation which comprises allowing a herbicidal effective amount of at least one pyrimidine compounds of the formula (I) to act on plants, their seed and/or their habitat.
Claims
1. The pyrimidine compound of formula (I), ##STR00327## wherein R.sup.1 is C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkyl, HO—C.sub.1-C.sub.6-alkyl, C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-haloalkenyl, C.sub.2-C.sub.6-alkynyl, C.sub.3-C.sub.6-haloalkynyl, C.sub.1-C.sub.6-alkoxy-C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-alkoxy, C.sub.3-C.sub.6-alkenyloxy, C.sub.3-C.sub.6-haloalkenyloxy, C.sub.3-C.sub.6-alkynyloxy, C.sub.3-C.sub.6-haloalkynyloxy, C.sub.1-C.sub.6-haloalkoxy, C.sub.3-C.sub.6-cycloalkoxy, C.sub.3-C.sub.6-halocycloalkoxy, C.sub.3-C.sub.6-cycloalkenyloxy, C.sub.3-C.sub.6-halocycloalkenyloxy, C.sub.1-C.sub.6-alkylthio, C.sub.1-C.sub.6-haloalkylthio, (C.sub.1-C.sub.6-alkyl)amino, di(C.sub.1-C.sub.6-alkyl)amino, C.sub.1-C.sub.6-alkylsulfinyl, C.sub.1-C.sub.6-alkylsulfonyl, C.sub.3-C.sub.6-cycloalkyl, C.sub.3-C.sub.6-cycloalkenyl, C.sub.3-C.sub.6-halocycloalkyl, C.sub.3-C.sub.6-halocycloalkenyl, [1-(C.sub.1-C.sub.6-alkyl)]-C.sub.3-C.sub.6-cycloalkyl, [1-(C.sub.2-C.sub.6-alkenyl)]-C.sub.3-C.sub.6-cycloalkyl, [1-(C.sub.2-C.sub.6-alkynyl)]-C.sub.3-C.sub.6-cycloalkyl, [1-(C.sub.1-C.sub.6-haloalkyl)]-C.sub.3-C.sub.6-cycloalkyl, [1-(C.sub.2-C.sub.6-haloalkenyl)]-C.sub.3-C.sub.6-cycloalkyl, [1-(C.sub.3-C.sub.6-haloalkynyl)]-C.sub.3-C.sub.6-cycloalkyl, C.sub.3-C.sub.6-cycloalkyl-C.sub.1-C.sub.6-alkyl, C.sub.3-C.sub.6-cycloalkyl-C.sub.1-C.sub.6-haloalkyl, C.sub.3-C.sub.6-cycloalkyl-C.sub.1-C.sub.6-alkoxy, C.sub.3-C.sub.6-cycloalkyl-C.sub.1-C.sub.6-haloalkoxy, or 3- to 6-membered heterocyclyl; wherein the cyclic groups of R.sup.1 are unsubstituted or substituted by R.sup.a; R.sup.a is halogen, CN, NO.sub.2, C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkyl, C.sub.1-C.sub.6-alkoxy, or C.sub.1-C.sub.6-haloalkoxy; R.sup.2 is C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkyl, C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-haloalkenyl, C.sub.1-C.sub.6-alkoxy-C.sub.2-C.sub.6-alkenyl, C.sub.1-C.sub.6-alkoxy-C.sub.2-C.sub.6-haloalkenyl, C.sub.1-C.sub.6-haloalkoxy-C.sub.2-C.sub.6-alkenyl, C.sub.1-C.sub.6-haloalkoxy-C.sub.2-C.sub.6-haloalkenyl, C.sub.2-C.sub.6-alkynyl, C.sub.2-C.sub.6-haloalkynyl, C.sub.1-C.sub.6-alkoxy-C.sub.2-C.sub.6-alkynyl, C.sub.1-C.sub.6-alkoxy-C.sub.3-C.sub.6-haloalkynyl, C.sub.1-C.sub.6-haloalkoxy-C.sub.2-C.sub.6-alkynyl, C.sub.1-C.sub.6-haloalkoxy-C.sub.3-C.sub.6-haloalkynyl, C.sub.3-C.sub.6-cycloalkyl, C.sub.3-C.sub.6-halocycloalkyl, C.sub.3-C.sub.6-cycloalkenyl, C.sub.3-C.sub.6-halocycloalkenyl, C.sub.3-C.sub.6-cycloalkyl-C.sub.1-C.sub.6-alkyl, C.sub.3-C.sub.6-cycloalkyl-C.sub.1-C.sub.6-haloalkyl, C.sub.3-C.sub.6-halocycloalkyl-C.sub.1-C.sub.6-alkyl, C.sub.3-C.sub.6-halocycloalkyl-C.sub.1-C.sub.6-haloalkyl, C.sub.3-C.sub.6-cycloalkenyl- C.sub.1-C.sub.6-alkyl, C.sub.3-C.sub.6-cycloalkenyl-C.sub.1-C.sub.6-haloalkyl, C.sub.3-C.sub.6-halocycloalkenyl- C.sub.1-C.sub.6-alkyl, C.sub.3-C.sub.6-halocycloalkenyl- C.sub.1-C.sub.6-haloalkyl, C.sub.3-C.sub.6-cycloalkyl-C.sub.2-C.sub.6-alkenyl, C.sub.3-C.sub.6-cycloalkyl-C.sub.2-C.sub.6-haloalkenyl, C.sub.3-C.sub.6-halocycloalkyl-C.sub.2-C.sub.6-alkenyl, C.sub.3-C.sub.6-halocycloalkyl-C.sub.2-C.sub.6-haloalkenyl, C.sub.3-C.sub.6-cycloalkenyl- C.sub.2-C.sub.6-alkenyl, C.sub.3-C.sub.6-cycloalkenyl- C.sub.2-C.sub.6-haloalkenyl, C.sub.3-C.sub.6-halocycloalkenyl- C.sub.2-C.sub.6-alkenyl, C.sub.3-C.sub.6-halocycloalkenyl- C.sub.2-C.sub.6-haloalkenyl, C.sub.3-C.sub.6-cycloalkyl-C.sub.2-C.sub.6-alkynyl, C.sub.3-C.sub.6-cycloalkyl-C.sub.3-C.sub.6-haloalkynyl, C.sub.3-C.sub.6-halocycloalkyl-C.sub.2-C.sub.6-alkynyl, C.sub.3-C.sub.6-halocycloalkyl-C.sub.3-C.sub.6-haloalkynyl, C.sub.3-C.sub.6-cycloalkenyl-C.sub.2-C.sub.6-alkynyl, C.sub.3-C.sub.6-cycloalkenyl-C.sub.3-C.sub.6-haloalkynyl, C.sub.3-C.sub.6-halocycloalkenyl-C.sub.2-C.sub.6-alkynyl, C.sub.3-C.sub.6-halocycloalkenyl-C.sub.3-C.sub.6-haloalkynyl, C.sub.3-C.sub.6-cycloalkyl-C.sub.1-C.sub.6-alkylidenyl, C.sub.3-C.sub.6-cycloalkyl-C.sub.2-C.sub.6-haloalkylidenyl, C.sub.3-C.sub.6-halocycloalkyl-C.sub.1-C.sub.6-alkylidenyl, C.sub.3-C.sub.6-halocycloalkyl-C.sub.2-C.sub.6-haloalkylidenyl, C.sub.3-C.sub.6-cycloalkenyl-C.sub.1-C.sub.6-alkylidenyl, C.sub.3-C.sub.6-cycloalkenyl-C.sub.2-C.sub.6-haloalkylidenyl, C.sub.3-C.sub.6-halocycloalkenyl-C.sub.1-C.sub.6-alkylidenyl, C.sub.3-C.sub.6-halocycloalkenyl-C.sub.2-C.sub.6-haloalkylidenyl, heterocyclyl-C.sub.1-C.sub.6-alkylidenyl, heterocyclyl-C.sub.1-C.sub.6-haloalkylidenyl, C.sub.3-C.sub.6-hydroxycycloalkyl-C.sub.1-C.sub.6-alkyl, C.sub.3-C.sub.6-hydroxycycloalkyl-C.sub.1-C.sub.6-haloalkyl, C.sub.3-C.sub.6-hydroxycycloalkenyl-C.sub.1-C.sub.6-alkyl, C.sub.3-C.sub.6-hydroxycycloalkenyl-C.sub.1-C.sub.6-haloalkyl, C.sub.1-C.sub.6-hydroxyalkyl, C.sub.2-C.sub.6-hydroxyhaloalkyl, C.sub.3-C.sub.6-hydroxyalkenyl, C.sub.3-C.sub.6-hydroxyhaloalkenyl, C.sub.3-C.sub.6-hydroxyalkynyl, C.sub.4-C.sub.6-hydroxyhaloalkynyl, C.sub.3-C.sub.6-hydroxycycloalkyl, C.sub.3-C.sub.6-hydroxyhalocycloalkyl, C.sub.3-C.sub.6-hydroxycycloalkenyl, C.sub.3-C.sub.6-hydroxyhalocycloalkenyl, C.sub.3-C.sub.6-cycloalkyl-C.sub.1-C.sub.6-hydroxyalkyl, C.sub.3-C.sub.6-cycloalkyl-C.sub.2-C.sub.6-hydroxyhaloalkyl, C.sub.3-C.sub.6-halocycloalkyl-C.sub.1-C.sub.6-hydroxyalkyl, C.sub.3-C.sub.6-halocycloalkyl-C.sub.2-C.sub.6-hydroxyhaloalkyl, C.sub.3-C.sub.6-cycloalkenyl-C.sub.1-C.sub.6-hydroxyalkyl, C.sub.3-C.sub.6-cycloalkenyl-C.sub.2-C.sub.6-hydroxyhaloalkyl, C.sub.3-C.sub.6-halocycloalkenyl-C.sub.1-C.sub.6-hydroxyalkylC.sub.3-C.sub.6-halocycloalkenyl-C.sub.2-C.sub.6-hydroxyhaloalkyl, C.sub.3-C.sub.6-cycloalkyl-C.sub.3-C.sub.6-hydroxyalkenyl, C.sub.3-C.sub.6-cycloalkyl-C.sub.3-C.sub.6-hydroxyhaloalkenyl, C.sub.3-C.sub.6-halocycloalkyl-C.sub.3-C.sub.6-hydroxyalkenyl, C.sub.3-C.sub.6-halocycloalkyl-C.sub.3-C.sub.6-hydroxyhaloalkenyl, C.sub.3-C.sub.6-cycloalkenyl-C.sub.3-C.sub.6-hydroxyalkenyl, C.sub.3-C.sub.6-cycloalkenyl-C.sub.3-C.sub.6-hydroxyhaloalkenyl, C.sub.3-C.sub.6-halocycloalkenyl-C.sub.3-C.sub.6-hydroxyalkenyl, C.sub.3-C.sub.6-halocycloalkenyl-C.sub.3-C.sub.6-hydroxyhaloalkenyl, C.sub.3-C.sub.6-cycloalkyl-C.sub.3-C.sub.6-hydroxyalkynyl, C.sub.3-C.sub.6-halocycloalkyl-C.sub.3-C.sub.6-hydroxyalkynyl, C.sub.3-C.sub.6-cycloalkenyl-C.sub.3-C.sub.6-hydroxyalkynyl, C.sub.3-C.sub.6-halocycloalkenyl-C.sub.3-C.sub.6-hydroxyalkynyl, C.sub.3-C.sub.6-cycloalkyl-C.sub.2-C.sub.6-hydroxyalkylidenyl, C.sub.3-C.sub.6-halocycloalkyl-C.sub.2-C.sub.6-hydroxyalkylidenyl, C.sub.3-C.sub.6-cycloalkenyl-C.sub.2-C.sub.6-hydroxyalkylidenyl, C.sub.3-C.sub.6-halocycloalkyl-C.sub.2-C.sub.6-hydroxyalkylidenyl, heterocyclyl-C.sub.2-C.sub.6-hydroxyalkylidenyl, hydroxy-carbonyl-C.sub.1-C.sub.6-hydroxyalkyl, hydroxycarbonyl-C.sub.1-C.sub.6-alkyl, hydroxycarbonyl-C.sub.1-C.sub.6-haloalkyl, C.sub.1-C.sub.6-alkoxycarbonyl-C.sub.1-C.sub.6-hydroxyalkyl, C.sub.1-C.sub.6-haloalkoxycarbonyl-C.sub.1-C.sub.6-hydroxyalkyl, C.sub.1-C.sub.6-alkoxycarbonyl-C.sub.1-C.sub.6-haloalkyl, C.sub.1-C.sub.6-haloalkoxycarbonyl-C.sub.1-C.sub.6-haloalkyl, C.sub.1-C.sub.6-alkoxycarbonyl-C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkoxycarbonyl-C.sub.1-C.sub.6-alkyl, C.sub.3-C.sub.6-hydroxycycloalkyl-C.sub.1-C.sub.6-hydroxyalkyl, C.sub.3-C.sub.6-hydroxycycloalkenyl-C.sub.1-C.sub.6-hydroxyalkyl, C.sub.3-C.sub.6-hydroxycycloalkyl-C.sub.3-C.sub.6-hydroxyalkenyl, C.sub.3-C.sub.6-hydroxycycloalkenyl-C.sub.3-C.sub.6-hydroxyalkenyl, C.sub.3-C.sub.6-hydroxycycloalkyl-C.sub.3-C.sub.6-hydroxyalkynyl, C.sub.3-C.sub.6-hydroxycycloalkenyl-C.sub.3-C.sub.6-hydroxyalkenyl, C.sub.2-C.sub.6-dihydroxyalkyl, C.sub.3-C.sub.6-dihydroxyhaloalkyl, C.sub.4-C.sub.6-dihydroxyalkenyl, C.sub.4-C.sub.6-dihydroxyhaloalkenyl, C.sub.4-C.sub.6-dihydroxyalkynyl, C.sub.5-C.sub.6-dihydroxyhaloalkynyl, C.sub.4-C.sub.6-dihydroxycycloalkyl, C.sub.4-C.sub.6-dihydroxyhalocycloalkyl, C.sub.4-C.sub.6-dihydroxycycloalkenyl, C.sub.4-C.sub.6-dihydroxyhalocycloalkenyl, C.sub.3-C.sub.6-cycloalkyl-C.sub.2-C.sub.6-dihydroxyalkyl, C.sub.3-C.sub.6-halocycloalkyl-C.sub.2-C.sub.6-dihydroxyalkyl, C.sub.3-C.sub.6-cycloalkenyl-C.sub.2-C.sub.6-dihydroxyalkyl, C.sub.3-C.sub.6-halocycloalkenyl-C.sub.2-C.sub.6-dihydroxyalkyl, C.sub.3-C.sub.6-cycloalkyl-C.sub.3-C.sub.6-dihydroxyalkenyl, C.sub.3-C.sub.6-halocycloalkyl-C.sub.3-C.sub.6-dihydroxyalkenyl, C.sub.3-C.sub.6-cycloalkenyl-C.sub.3-C.sub.6-dihydroxyalkenyl, C.sub.3-C.sub.6-halocycloalkenyl-C.sub.3-C.sub.6-dihydroxyalkenyl, C.sub.3-C.sub.6-cycloalkyl-C.sub.4-C.sub.6-dihydroxyalkynyl, C.sub.3-C.sub.6-halocycloalkyl-C.sub.4-C.sub.6-dihydroxyalkynyl, C.sub.3-C.sub.6-cycloalkenyl-C.sub.4-C.sub.6-dihydroxyalkynyl, C.sub.3-C.sub.6-halocycloalkyl-C.sub.4-C.sub.6-dihydroxyalkynyl, C.sub.3-C.sub.6-cycloalkyl-C.sub.3-C.sub.6-dihydroxyalkylidenyl, C.sub.3-C.sub.6-halocycloalkyl-C.sub.3-C.sub.6-dihydroxyalkylidenyl, heterocyclyl-C.sub.3-C.sub.6-dihydroxyalkylidenyl, hydroxycarbonyl-C.sub.2-C.sub.6-dihydroxyalkyl, hydroxycarbonyl-C.sub.3-C.sub.6-dihydroxyhaloalkyl, C.sub.1-C.sub.6-alkoxycarbonyl-C.sub.2-C.sub.6-dihydroxyalkyl, C.sub.1-C.sub.6-haloalkoxycarbonyl-C.sub.2-C.sub.6-dihydroxyalkyl, C.sub.1-C.sub.6-haloalkoxycarbonyl-C.sub.3-C.sub.6-dihydroxyhaloalkyl, C.sub.3-C.sub.6-dihydroxycycloalkyl-C.sub.1-C.sub.6-alkyl, C.sub.3-C.sub.6-dihydroxycycloalkyl-C.sub.1-C.sub.6-haloalkyl, C.sub.3-C.sub.6-dihydroxycycloalkyl-C.sub.2-C.sub.6-alkenyl, C.sub.3-C.sub.6-dihydroxycycloalkyl-C.sub.2-C.sub.6-haloalkenyl, C.sub.3-C.sub.6-dihydroxycycloalkyl-C.sub.2-C.sub.6-alkynyl, C.sub.3-C.sub.6-dihydroxycycloalkyl-C.sub.3-C.sub.6-haloalkynyl, C.sub.1-C.sub.6-alkylcarbonyl-C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkylcarbonyl-C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-alkylcarbonyl-C.sub.1-C.sub.6-haloalkyl, C.sub.1-C.sub.6-haloalkylcarbonyl-C.sub.1-C.sub.6-haloalkyl, hydroxycarbonyl-C.sub.2-C.sub.6-alkenyl, hydroxycarbonyl-C.sub.2-C.sub.6-haloalkenyl, C.sub.1-C.sub.6-alkoxycarbonyl-C.sub.2-C.sub.6-alkenyl, C.sub.1-C.sub.6-haloalkoxycarbonyl-C.sub.2-C.sub.6-alkenyl, C.sub.1-C.sub.6-alkoxycarbonyl-C.sub.2-C.sub.6-haloalkenyl, C.sub.1-C.sub.6-haloalkoxycarbonyl-C.sub.2-C.sub.6-haloalkenyl, hydroxycarbonyl-C.sub.2-C.sub.6-alkynyl, hydroxycarbonyl-C.sub.3-C.sub.6-haloalkynyl, C.sub.1-C.sub.6-alkoxycarbonyl-C.sub.2-C.sub.6-alkynyl, C.sub.1-C.sub.6-haloalkoxycarbonyl-C.sub.2-C.sub.6-alkynyl, C.sub.1-C.sub.6-alkoxycarbonyl-C.sub.3-C.sub.6-halo-alkynyl, C.sub.1-C.sub.6-haloalkoxycarbonyl-C.sub.3-C.sub.6-haloalkynyl, C.sub.1-C.sub.6-cyanoalkyl, C.sub.2-C.sub.6-cyanohaloalkyl, C.sub.1-C.sub.6-dicyanoalkyl, C.sub.2-C.sub.6-dicyanohaloalkyl, di(hydroxycarbonyl)-C.sub.1-C.sub.6-alkyl, di(hydroxycarbonyl)-C.sub.1-C.sub.6-haloalkyl, di(C.sub.1-C.sub.6-alkoxycarbonyl)-C.sub.1-C.sub.6-alkyl, di(C.sub.1-C.sub.6-haloalkoxycarbonyl)-C.sub.1-C.sub.6-alkyl, di(C.sub.1-C.sub.6-alkoxycarbonyl)-C.sub.1-C.sub.6-haloalkyl, di(C.sub.1-C.sub.6-haloalkoxycarbonyl)-C.sub.1-C.sub.6-haloalkyl, di(C.sub.1-C.sub.6-alkoxyl)phosphoryl-C.sub.1-C.sub.6-alkyl, di(C.sub.1-C.sub.6-haloalkoxyl)phosphoryl-C.sub.1-C.sub.6-alkyl, di(C.sub.1-C.sub.6-alkoxyl)phosphoryl-C.sub.1-C.sub.6-haloalkyl, di(C.sub.1-C.sub.6-haloalkoxyl)phosphoryl-C.sub.1-C.sub.6-haloalkyl, phosphoryl-C.sub.1-C.sub.6-alkyl, phosphoryl-C.sub.1-C.sub.6-haloalkyl, di[di(C.sub.1-C.sub.6-alkoxyl)phosphoryl-)]C.sub.1-C.sub.6-alkyl, di[di(C.sub.1-C.sub.6-haloalkoxyl)phosphoryl-)]C.sub.1-C.sub.6-alkyl, di[di(C.sub.1-C.sub.6-alkoxyl)phosphoryl-)]C.sub.1-C.sub.6-haloalkyl, di[di(C.sub.1-C.sub.6-haloalkoxyl)phosphoryl-)]C.sub.1-C.sub.6-haloalkyl, diphosphoryl-C.sub.1-C.sub.6-alkyl, diphosphoryl-C.sub.1-C.sub.6-haloalkyl, C.sub.1-C.sub.6-alkylthio-C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkylthio-C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-alkylthio-C.sub.1-C.sub.6-haloalkyl, C.sub.1-C.sub.6-haloalkylthio-C.sub.1-C.sub.6-haloalkyl, C.sub.1-C.sub.6-alkylsulfinly-C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkylsulfinly-C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-alkylsulfinly-C.sub.1-C.sub.6-haloalkyl, C.sub.1-C.sub.6-haloalkylsulfinly-C.sub.1-C.sub.6-haloalkyl, C.sub.1-C.sub.6-alkylsulfonyl-C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkylsulfonyl-C.sub.1-C.sub.6-haloalkyl, phenyl, 5-, 6- or 9 membered heteroaryl, 3- to 6-membered heterocyclyl, (C.sub.1-C.sub.6-alkyl)carbonylaminocarbonyl, (C.sub.2-C.sub.6-alkenyl)carbo-nylamino-carbonyl, (C.sub.3-C.sub.6-alkynyl)carbonylaminocarbonyl, (C.sub.1-C.sub.6-haloalkyl)carbo-nylaminocarbonyl, (C.sub.2-C.sub.6-haloalkenyl)carbonylaminocarbonyl, (C.sub.3-C.sub.6-haloalkynyl)car-bonylaminocarbonyl, phenylcarbonylaminocarbonyl, (C.sub.3-C.sub.6-cycloalkyl)carbonylaminocarbonyl, [(C.sub.1-C.sub.6-alkyl)amino]carbonylaminocarbonyl, or [di(C.sub.1-C.sub.6-alkyl)amino]carbonylaminocarbonyl, heterocyclylcarbonylaminocarbonyl, heteroarylcarbonylaminocarbonyl, phenylcarbonylaminocarbonyl; wherein OH groups of R.sup.2 are unsubstituted or substituted by R.sup.b; cyclic groups of R.sup.2 are unsubstituted or substituted by R.sup.c; and acyclic aliphatic groups of R.sup.2 are unsubstituted or substituted by R.sup.d; R.sup.b is C.sub.1-C.sub.6-alkyl, C.sub.3-C.sub.6-alkenyl, C.sub.3-C.sub.6-haloalkenyl, C.sub.3-C.sub.6-alkynyl, C.sub.3-C.sub.6-haloalkynyl, C.sub.3-C.sub.6-cycloalkyl, C.sub.3-C.sub.6-halocycloalkyl, C.sub.4-C.sub.6-cycloalkenyl, C.sub.3-C.sub.6-halocycloalkenyl, C.sub.1-C.sub.6-alkoxycarbonyl-C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkoxycarbonyl-C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-alkoxycarbonyl-C.sub.1-C.sub.6-haloalkyl, C.sub.1-C.sub.6-haloalkoxycarbonyl-C.sub.1-C.sub.6-haloalkyl, C.sub.1-C.sub.6-alkylcarbonyl, C.sub.1-C.sub.6-haloalkylcarbonyl, hydroxycarbonyl-C.sub.1-C.sub.6-alkyl, hydroxycarbonyl-C.sub.1-C.sub.6-haloalkyl, C.sub.1-C.sub.6-alkyloxycarbonyl, C.sub.1-C.sub.6-haloalkyloxycarbonyl, C.sub.1-C.sub.6-alkylthiocarbonyl, C.sub.1-C.sub.6-haloalkylthiocarbonyl, C.sub.1-C.sub.6-alkylaminocarbonyl, C.sub.1-C.sub.6-haloalkylaminocarbonyl, C.sub.1-C.sub.6-dialkylaminocarbonyl, C.sub.1-C.sub.6-dihaloalkylaminocarbonyl, C.sub.1-C.sub.6-alkylsulfonyl, C.sub.1-C.sub.6-haloalkylsulfonyl, C.sub.1-C.sub.6-haloalkoxy-C.sub.1-C.sub.6-haloalkyl, phenyl-C.sub.1-C.sub.6-alkyl, or phenyl-C.sub.1-C.sub.6-haloalkyl; R.sup.c is halogen, CN, NO.sub.2, C.sub.1-C.sub.6-haloalkyl, OH, C.sub.1-C.sub.6-alkoxy, C.sub.1-C.sub.6-haloalkoxy, C.sub.1-C.sub.6-alkylsulfinyl, or C.sub.1-C.sub.6-alkylsulfonyl; R.sup.d is phenyl, 5- or 6-membered heteroaryl, or 3- to 6-membered heterocyclyl; wherein the substituent R.sup.d is unsubstituted or substituted by R.sup.e; R.sup.e is halogen, CN, NO.sub.2, C.sub.1-C.sub.6-haloalkyl, OH, C.sub.1-C.sub.6-alkoxy, C.sub.1-C.sub.6-haloalkoxy, C.sub.1-C.sub.6-alkylsulfonyl; R.sup.3 is halogen, CN, NO.sub.2, C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkyl, C.sub.1-C.sub.6-alkylcarbonyl, C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-haloalkenyl, C.sub.2-C.sub.6-alkynyl, C.sub.2-C.sub.6-haloalkynyl, C.sub.1-C.sub.6-alkoxy, C.sub.1-C.sub.6-halo-alkoxy, C.sub.3-C.sub.6-alkenyloxy, C.sub.3-C.sub.6-haloalkenyloxy, C.sub.3-C.sub.6-alkynyloxy, C.sub.3-C.sub.6-haloalkynyloxy, C.sub.1-C.sub.6-alkoxy-C.sub.1-C.sub.6-alkoxy, hydroxycarbonyl, C.sub.1-C.sub.6-alkoxycarbonyl, C.sub.1-C.sub.6-alkylthio, C.sub.1-C.sub.6-haloalkylthio, NH.sub.2, (C.sub.1-C.sub.6-alkyl)amino, di(C.sub.1-C.sub.6-alkyl)amino, (C.sub.1-C.sub.6-alkyl)sulfinyl, (C.sub.1-C.sub.6-alkyl)sulfonyl, C.sub.3-C.sub.6-cycloalkyl, (C.sub.3-C.sub.6-cycloalkyl)oxy or phenyl; wherein the cyclic groups of R.sup.3 are unsubstituted or substituted by substituents R.sup.a; R.sup.4, R.sup.5, R.sup.6 and R.sup.7 independently of one another are H, halogen, CN, NO.sub.2, C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkyl, C.sub.1-C.sub.6-alkylcarbonyl, C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-haloalkenyl, C.sub.2-C.sub.6-alkynyl, C.sub.2-C.sub.6-haloalkynyl, C.sub.1-C.sub.6-alkoxy, C.sub.1-C.sub.6-haloalkoxy, C.sub.3-C.sub.6-alkenyloxy, C.sub.3-C.sub.6-haloalkenyloxy, C.sub.3-C.sub.6-alkynyloxy, C.sub.3-C.sub.6-haloalkynyloxy, C.sub.1-C.sub.6-alkoxy-C.sub.1-C.sub.6-alkoxy, hydroxycarbonyl, C.sub.1-C.sub.6-alkoxycarbonyl, C.sub.1-C.sub.6-alkylthio, C.sub.1-C.sub.6-haloalkylthio, NH.sub.2, (C.sub.1-C.sub.6-alkyl)amino, di(C.sub.1-C.sub.6-alkyl)amino, (C.sub.1-C.sub.6-alkyl)sulfinyl, (C.sub.1-C.sub.6-alkyl)sulfonyl, C.sub.3-C.sub.6-cycloalkyl, (C.sub.3-C.sub.6-cycloalkyl)oxy or phenyl; wherein the cyclic groups of R.sup.4 R.sup.5, R.sup.6 and R.sup.7 are unsubstituted or substituted by R.sup.a; or an agriculturally acceptable salt, amide, ester, or thioester of the pyrimidine compound of formula (I); with the exception of 5-(2-bromophenyl)-2-cyclopropyl-4-methyl-pyrimidine; 5-(2-bromophenyl)-2-ethyl-4- methyl-pyrimidine; and 5-(2-bromophenyl)-2-methoxy-4- methyl-pyrimidine.
2. The pyrimidine compound of formula (I) according to claim 1, wherein R.sup.1 is C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-alkoxy, C.sub.1-C.sub.6-haloalkoxy, C.sub.3-C.sub.6-alkenyloxy, C.sub.3-C.sub.6-haloalkenyloxy, C.sub.3-C.sub.6-alkynyloxy, C.sub.4-C.sub.6-haloalkynyloxy, C.sub.1-C.sub.6-alkylthio, or C.sub.3-C.sub.6-cycloalkyl wherein cycloalkyl is unsubstituted.
3. The pyrimidine compound of formula (I) according to claim 1, wherein R.sup.2 C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-haloalkenyl, C.sub.1-C.sub.6-alkoxy-C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-alkynyl, C.sub.3-C.sub.6-cycloalkenyl, C.sub.3-C.sub.6-cycloalkenyl-C.sub.1-C.sub.6-alkyl, C.sub.3-C.sub.6-cycloalkyl-C.sub.1-C.sub.6-alkylidenyl, C.sub.3-C.sub.6-halocycloalkyl-C.sub.1-C.sub.6-alkylidenyl, C.sub.3-C.sub.6-cycloalkenyl-C.sub.1-C.sub.6-alkylidenyl, C.sub.3-C.sub.6-hydroxycycloalkyl-C.sub.1-C.sub.6-alkyl, C.sub.3-C.sub.6-hydroxycycloalkenyl-C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-hydroxyalkyl, C.sub.3-C.sub.6-cycloalkyl-C.sub.2-C.sub.6-hydroxyalkylidenyl, hydroxycarbonyl-C.sub.1-C.sub.6-alkyl, hydroxycarbonyl-C.sub.1-C.sub.6-haloalkyl, C.sub.1-C.sub.6-alkoxycarbonyl-C.sub.1-C.sub.6-alkyl, C.sub.3-C.sub.6-hydroxycycloalkyl-C.sub.1-C.sub.6-hydroxyalkyl, C.sub.2-C.sub.6-dihydroxyalkyl, C.sub.3-C.sub.6-cycloalkyl-C.sub.3-C.sub.6-dihydroxyalkylidenyl, hydroxycarbonyl-C.sub.2-C.sub.6-dihydroxyalkyl, C.sub.1-C.sub.6-alkoxycarbonyl-C.sub.2-C.sub.6-dihydroxyalkyl, C.sub.1-C.sub.6-dicyanoalkyl, 5- or 6-membered heteroaryl, or (C.sub.1-C.sub.6-alkyl)carbonylaminocarbonyl; wherein OH groups of R.sup.2 are unsubstituted or substituted by R.sup.b, cyclic groups of R.sup.2 are unsubstituted or substituted by R.sup.c, and acyclic aliphatic groups of R.sup.2 are unsubstituted or substituted by R.sup.d; R.sup.b is C.sub.1-C.sub.6-alkyl, C.sub.3-C.sub.6-alkenyl, C.sub.3-C.sub.6-haloalkenyl, C.sub.3-C.sub.6-alkynyl, C.sub.3-C.sub.6-haloalkynyl, C.sub.3-C.sub.6-cycloalkyl, C.sub.3-C.sub.6-halocycloalkyl, C.sub.4-C.sub.6-cycloalkenyl, C.sub.3-C.sub.6-halocycloalkenyl, C.sub.1-C.sub.6-alkoxycarbonyl-C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkoxycarbonyl-C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-alkoxycarbonyl-C.sub.1-C.sub.6-haloalkyl, C.sub.1-C.sub.6-haloalkoxycarbonyl-C.sub.1-C.sub.6-haloalkyl, C.sub.1-C.sub.6-alkylcarbonyl, C.sub.1-C.sub.6-haloalkylcarbonyl, hydroxycarbonyl-C.sub.1-C.sub.6-alkyl, hydroxycarbonyl-C.sub.1-C.sub.6-haloalkyl, C.sub.1-C.sub.6-alkyloxycarbonyl, C.sub.1-C.sub.6-haloalkyloxycarbonyl, C.sub.1-C.sub.6-alkylthiocarbonyl, C.sub.1-C.sub.6-haloalkylthiocarbonyl, C.sub.1-C.sub.6-alkylaminocarbonyl, C.sub.1-C.sub.6-haloalkylaminocarbonyl, C.sub.1-C.sub.6-dialkylaminocarbonyl, C.sub.1-C.sub.6-dihaloalkylaminocarbonyl, C.sub.1-C.sub.6-alkylsulfonyl, C.sub.1-C.sub.6-haloalkylsulfonyl, C.sub.1-C.sub.6-haloalkoxy-C.sub.1-C.sub.6-haloalkyl, phenyl-C.sub.1-C.sub.6-alkyl, or phenyl-C.sub.1-C.sub.6-haloalkyl; R.sup.c is halogen, CN, NO.sub.2, C.sub.1-C.sub.6-haloalkyl, OH, C.sub.1-C.sub.6-alkoxy, C.sub.1-C.sub.6-haloalkoxy, C.sub.1-C.sub.6-alkylsulfinyl, or C.sub.1-C.sub.6-alkylsulfonyl; R.sup.d is phenyl, 5- or 6-membered heteroaryl, or 3- to 6-membered heterocyclyl; wherein the substituent R.sup.d is unsubstituted or substituted by R.sup.e; R.sup.e is halogen, CN, NO.sub.2, C.sub.1-C.sub.6-haloalkyl, OH, C.sub.1-C.sub.6-alkoxy, C.sub.1-C.sub.6-haloalkoxy, C.sub.1-C.sub.6-alkylsulfonyl.
4. The pyrimidine compound of formula (I) according to claim 1, wherein R.sup.3 is halogen, CN, NO.sub.2, C.sub.1-C.sub.6-alkoxy, or C.sub.3-C.sub.6-cycloalkyl; R.sup.4 is H, halogen, CN, C.sub.1-C.sub.6-haloalkyl, or C.sub.1-C.sub.6-alkoxy; R.sup.5 is H, halogen, CN, C.sub.1-C.sub.6-haloalkyl, or C.sub.1-C.sub.6-alkoxy; R.sup.6 is H, halogen, C.sub.1-C.sub.6-alkyl, or C.sub.1-C.sub.6-haloalkyl; R.sup.7 is H, halogen, CN, C.sub.1-C.sub.6-alkyl, or C.sub.1-C.sub.6-alkoxy.
5. The pyrimidine compound of formula (I) according to claim 1, wherein R.sup.1 is c-C.sub.3H.sub.5; R.sup.2 is C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-haloalkenyl, C.sub.1-C.sub.6-alkoxy-C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-alkynyl, C.sub.3-C.sub.6-cycloalkenyl, C.sub.3-C.sub.6-cycloalkenyl-C.sub.1-C.sub.6-alkyl, C.sub.3-C.sub.6-cycloalkyl-C.sub.1-C.sub.6-alkylidenyl, C.sub.3-C.sub.6-halocycloalkyl-C.sub.1-C.sub.6-alkylidenyl, C.sub.3-C.sub.6-cycloalkenyl-C.sub.1-C.sub.6-alkylidenyl, C.sub.3-C.sub.6-hydroxycycloalkyl-C.sub.1-C.sub.6-alkyl, C.sub.3-C.sub.6-hydroxycycloalkenyl-C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-hydroxyalkyl, C.sub.3-C.sub.6-cycloalkyl-C.sub.2-C.sub.6-hydroxyalkylidenyl, hydroxycarbonyl-C.sub.1-C.sub.6-alkyl, hydroxycarbonyl-C.sub.1-C.sub.6-haloalkyl, C.sub.1-C.sub.6-alkoxycarbonyl-C.sub.1-C.sub.6-alkyl, C.sub.3-C.sub.6-hydroxycycloalkyl-C.sub.1-C.sub.6-hydroxyalkyl, C.sub.2-C.sub.6-dihydroxyalkyl, C.sub.3-C.sub.6-cycloalkyl-C.sub.3-C.sub.6-dihydroxyalkylidenyl, hydroxycarbonyl-C.sub.2-C.sub.6-dihydroxyalkyl, C.sub.1-C.sub.6-alkoxycarbonyl-C.sub.2-C.sub.6-dihydroxyalkyl, C.sub.1-C.sub.6-dicyanoalkyl, 5- or 6-membered heteroaryl, or (C.sub.1-C.sub.6-alkyl)carbonylaminocarbonyl; wherein OH groups of R.sup.2 are unsubstituted or substituted by R.sup.b, cyclic groups of R.sup.2 are unsubstituted or substituted by R.sup.c, and acyclic aliphatic groups of R.sup.2 are unsubstituted or substituted by R.sup.d; R.sup.b is C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkyl, C.sub.3-C.sub.6-alkenyl, C.sub.3-C.sub.6-haloalkenyl, C.sub.3-C.sub.6-alkynyl, C.sub.3-C.sub.6-haloalkynyl, C.sub.3-C.sub.6-cycloalkyl, C.sub.3-C.sub.6-halocycloalkyl, C.sub.4-C.sub.6-cycloalkenyl, C.sub.3-C.sub.6-halocycloalkenyl, C.sub.1-C.sub.6-alkoxycarbonyl-C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkoxycarbonyl-C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-alkoxycarbonyl-C.sub.1-C.sub.6-haloalkyl, C.sub.1-C.sub.6-haloalkoxycarbonyl-C.sub.1-C.sub.6-haloalkyl, C.sub.1-C.sub.6-alkylcarbonyl, C.sub.1-C.sub.6-haloalkylcarbonyl, hydroxycarbonyl-C.sub.1-C.sub.6-alkyl, hydroxycarbonyl-C.sub.1-C.sub.6-haloalkyl, C.sub.1-C.sub.6-alkyloxycarbonyl, C.sub.1-C.sub.6-haloalkyloxycarbonyl, C.sub.1-C.sub.6-alkylthiocarbonyl, C.sub.1-C.sub.6-haloalkylthiocarbonyl, C.sub.1-C.sub.6-alkylaminocarbonyl, C.sub.1-C.sub.6-haloalkylaminocarbonyl, C.sub.1-C.sub.6-dialkylaminocarbonyl, C.sub.1-C.sub.6-dihaloalkylaminocarbonyl, C.sub.1-C.sub.6-alkylsulfonyl, C.sub.1-C.sub.6-haloalkylsulfonyl, C.sub.1-C.sub.6-alkoxy-C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkoxy-C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-alkoxy-C.sub.1-C.sub.6-haloalkyl, C.sub.1-C.sub.6-haloalkoxy-C.sub.1-C.sub.6-haloalkyl, phenyl-C.sub.1-C.sub.6-alkyl, or phenyl-C.sub.1-C.sub.6-haloalkyl; R.sup.c is halogen, CN, NO.sub.2, C.sub.1-C.sub.6-haloalkyl, OH, C.sub.1-C.sub.6-alkoxy, C.sub.1-C.sub.6-haloalkoxy, C.sub.1-C.sub.6-alkylsulfinyl, or C.sub.1-C.sub.6-alkylsulfonyl; R.sup.d is phenyl, 5- or 6-membered heteroaryl, or 3- to 6-membered heterocyclyl; wherein the substituent R.sup.d is unsubstituted or substituted by R.sup.e; R.sup.e is halogen, CN, NO.sub.2, C.sub.1-C.sub.6-haloalkyl, OH, C.sub.1-C.sub.6-alkoxy, C.sub.1-C.sub.6-haloalkoxy, C.sub.1-C.sub.6-alkylsulfonyl; R.sup.3 is Cl, Br, I, CH.sub.3, CF.sub.3, or CF.sub.2H; R.sup.4 is H; R.sup.5 is H or F; R.sup.6 is H, F, CF.sub.3, Cl, or Br; R.sup.7 is H or F.
6. The pyrimidine compound of formula (I) according to claim 1 which corresponds to formula I.K, ##STR00328## wherein X and Y independently are selected from H, CH.sub.3, C.sub.2H.sub.5, n-propyl, iso-propyl, iso-butyl, n-butyl, 2-butyl, t-butyl, OH, OCH.sub.3, SCH.sub.3, S(O)CH.sub.3, S(O).sub.2CH.sub.3, CN, F, C.sub.1, Br, I, CH.sub.2CF.sub.3, CF.sub.2CF.sub.3, CF.sub.2CH.sub.3, CF.sub.3, CF.sub.2H, OCF.sub.2H, and OCF.sub.3; R.sup.1 is c-C.sub.3H.sub.5; R.sup.3 is Cl, Br, I, CH.sub.3, CF.sub.3, or CF.sub.2H; R.sup.5 is H or F; R.sup.6 is H, F, CF.sub.3, Cl, or Br; R.sup.7 is H or F.
7. A herbicidal mixture comprising: A) at least one compound of formula I, including agriculturally acceptable salts or derivatives of the pyrimidine compound of formula (I) having an acidic functionality, one pyrimidine compound of formula (I), ##STR00329## wherein: R.sup.1 is C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkyl, HO—C.sub.1-C.sub.6-alkyl, C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-haloalkenyl, C.sub.2-C.sub.6-alkynyl, C.sub.3-C.sub.6-haloalkynyl, C.sub.1-C.sub.6-alkoxy-C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-alkoxy, C.sub.3-C.sub.6-alkenyloxy, C.sub.3-C.sub.6-haloalkenyloxy, C.sub.3-C.sub.6-alkynyloxy, C.sub.3-C.sub.6-haloalkynyloxy, C.sub.1-C.sub.6-haloalkoxy, C.sub.3-C.sub.6-cycloalkoxy, C.sub.3-C.sub.6-halocycloalkoxy, C.sub.3-C.sub.6-cycloalkenyloxy, C.sub.3-C.sub.6-halocycloalkenyloxy, C.sub.1-C.sub.6-alkylthio, C.sub.1-C.sub.6-haloalkylthio, (C.sub.1-C.sub.6-alkyl)amino, di(C.sub.1-C.sub.6-alkyl)amino, C.sub.1-C.sub.6-alkylsulfinyl, C.sub.1-C.sub.6-alkylsulfonyl, C.sub.3-C.sub.6-cycloalkyl, C.sub.3-C.sub.6-cycloalkenyl, C.sub.3-C.sub.6-halocycloalkyl, C.sub.3-C.sub.6-halocycloalkenyl, [1-(C.sub.1-C.sub.6-alkyl)]-C.sub.3-C.sub.6-cycloalkyl, [1-(C.sub.2-C.sub.6-alkenyl)]-C.sub.3-C.sub.6-cycloalkyl, [1-(C.sub.2-C.sub.6-alkynyl)]-C.sub.3-C.sub.6-cycloalkyl, [1-(C.sub.1-C.sub.6-haloalkyl)]-C.sub.3-C.sub.6-cycloalkyl, [1-(C.sub.2-C.sub.6-haloalkenyl)]-C.sub.3-C.sub.6-cycloalkyl, [1-(C.sub.3-C.sub.6-haloalkynyl)]-C.sub.3-C.sub.6-cycloalkyl, C.sub.3-C.sub.6-cycloalkyl-C.sub.1-C.sub.6-alkyl, C.sub.3-C.sub.6-cycloalkyl-C.sub.1-C.sub.6-haloalkyl, C.sub.3-C.sub.6-cycloalkyl-C.sub.1-C.sub.6-alkoxy, C.sub.3-C.sub.6-cycloalkyl-C.sub.1-C.sub.6-haloalkoxy, or 3- to 6-membered heterocyclyl; wherein the cyclic groups of R.sup.1 are unsubstituted or substituted by R.sup.a; R.sup.2 is C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkyl, C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-haloalkenyl, C.sub.1-C.sub.6-alkoxy-C.sub.2-C.sub.6-alkenyl, C.sub.1-C.sub.6-alkoxy-C.sub.2-C.sub.6-haloalkenyl, C.sub.1-C.sub.6-haloalkoxy-C.sub.2-C.sub.6-alkenyl, C.sub.1-C.sub.6-haloalkoxy-C.sub.2-C.sub.6-haloalkenyl, C.sub.2-C.sub.6-alkynyl, C.sub.2-C.sub.6-haloalkynyl, C.sub.1-C.sub.6-alkoxy-C.sub.2-C.sub.6-alkynyl, C.sub.1-C.sub.6-alkoxy-C.sub.3-C.sub.6-haloalkynyl, C.sub.1-C.sub.6-haloalkoxy-C.sub.2-C.sub.6-alkynyl, C.sub.1-C.sub.6-haloalkoxy-C.sub.3-C.sub.6-haloalkynyl, C.sub.3-C.sub.6-cycloalkyl, C.sub.3-C.sub.6-halocycloalkyl, C.sub.3-C.sub.6-cycloalkenyl, C.sub.3-C.sub.6-halocycloalkenyl, C.sub.3-C.sub.6-cycloalkyl-C.sub.1-C.sub.6-alkyl, C.sub.3-C.sub.6-cycloalkyl-C.sub.1-C.sub.6-haloalkyl, C.sub.3-C.sub.6-halocycloalkyl-C.sub.1-C.sub.6-alkyl, C.sub.3-C.sub.6-halocycloalkyl-C.sub.1-C.sub.6-haloalkyl, C.sub.3-C.sub.6-cycloalkenyl- C.sub.1-C.sub.6-alkyl, C.sub.3-C.sub.6-cycloalkenyl-C.sub.1-C.sub.6-haloalkyl, C.sub.3-C.sub.6-halocycloalkenyl- C.sub.1-C.sub.6-alkyl, C.sub.3-C.sub.6-halocycloalkenyl- C.sub.1-C.sub.6-haloalkyl, C.sub.3-C.sub.6-cycloalkyl-C.sub.2-C.sub.6-alkenyl, C.sub.3-C.sub.6-cycloalkyl-C.sub.2-C.sub.6-haloalkenyl, C.sub.3-C.sub.6-halocycloalkyl-C.sub.2-C.sub.6-alkenyl, C.sub.3-C.sub.6-halocycloalkyl-C.sub.2-C.sub.6-haloalkenyl, C.sub.3-C.sub.6-cycloalkenyl- C.sub.2-C.sub.6-alkenyl, C.sub.3-C.sub.6-cycloalkenyl- C.sub.2-C.sub.6-haloalkenyl, C.sub.3-C.sub.6-halocycloalkenyl- C.sub.2-C.sub.6-alkenyl, C.sub.3-C.sub.6-halocycloalkenyl- C.sub.2-C.sub.6-haloalkenyl, C.sub.3-C.sub.6-cycloalkyl-C.sub.2-C.sub.6-alkynyl, C.sub.3-C.sub.6-cycloalkyl-C.sub.3-C.sub.6-haloalkynyl, C.sub.3-C.sub.6-halocycloalkyl-C.sub.2-C.sub.6-alkynyl, C.sub.3-C.sub.6-halocycloalkyl-C.sub.3-C.sub.6-haloalkynyl, C.sub.3-C.sub.6-cycloalkenyl-C.sub.2-C.sub.6-alkynyl, C.sub.3-C.sub.6-cycloalkenyl-C.sub.3-C.sub.6-haloalkynyl, C.sub.3-C.sub.6-halocycloalkenyl-C.sub.2-C.sub.6-alkynyl, C.sub.3-C.sub.6-halocycloalkenyl-C.sub.3-C.sub.6-haloalkynyl, C.sub.3-C.sub.6-cycloalkyl-C.sub.1-C.sub.6-alkylidenyl, C.sub.3-C.sub.6-cycloalkyl-C.sub.2-C.sub.6-haloalkylidenyl, C.sub.3-C.sub.6-halocycloalkyl-C.sub.1-C.sub.6-alkylidenyl, C.sub.3-C.sub.6-halocycloalkyl-C.sub.2-C.sub.6-haloalkylidenyl, C.sub.3-C.sub.6-cycloalkenyl-C.sub.1-C.sub.6-alkylidenyl, C.sub.3-C.sub.6-cycloalkenyl-C.sub.2-C.sub.6-haloalkylidenyl, C.sub.3-C.sub.6-halocycloalkenyl-C.sub.1-C.sub.6-alkylidenyl, C.sub.3-C.sub.6-halocycloalkenyl-C.sub.2-C.sub.6-haloalkylidenyl, heterocyclyl-C.sub.1-C.sub.6-alkylidenyl, heterocyclyl-C.sub.1-C.sub.6-haloalkylidenyl, C.sub.3-C.sub.6-hydroxycycloalkyl-C.sub.1-C.sub.6-alkyl, C.sub.3-C.sub.6-hydroxycycloalkyl-C.sub.1-C.sub.6-haloalkyl, C.sub.3-C.sub.6-hydroxycycloalkenyl-C.sub.1-C.sub.6-alkyl, C.sub.3-C.sub.6-hydroxycycloalkenyl-C.sub.1-C.sub.6-haloalkyl, C.sub.1-C.sub.6-hydroxyalkyl, C.sub.2-C.sub.6-hydroxyhaloalkyl, C.sub.3-C.sub.6-hydroxyalkenyl, C.sub.3-C.sub.6-hydroxyhaloalkenyl, C.sub.3-C.sub.6-hydroxyalkynyl, C.sub.4-C.sub.6-hydroxyhaloalkynyl, C.sub.3-C.sub.6-hydroxycycloalkyl, C.sub.3-C.sub.6-hydroxyhalocycloalkyl, C.sub.3-C.sub.6-hydroxycycloalkenyl, C.sub.3-C.sub.6-hydroxyhalocycloalkenyl, C.sub.3-C.sub.6-cycloalkyl-C.sub.1-C.sub.6-hydroxyalkyl, C.sub.3-C.sub.6-cycloalkyl-C.sub.2-C.sub.6-hydroxyhaloalkyl, C.sub.3-C.sub.6-halocycloalkyl-C.sub.1-C.sub.6-hydroxyalkyl, C.sub.3-C.sub.6-halocycloalkyl-C.sub.2-C.sub.6-hydroxyhaloalkyl, C.sub.3-C.sub.6-cycloalkenyl-C.sub.1-C.sub.6-hydroxyalkyl, C.sub.3-C.sub.6-cycloalkenyl-C.sub.2-C.sub.6-hydroxyhaloalkyl, C.sub.3-C.sub.6-halocycloalkenyl-C.sub.1-C.sub.6-hydroxyalkylC.sub.3-C.sub.6-halocycloalkenyl-C.sub.2-C.sub.6-hydroxyhaloalkyl, C.sub.3-C.sub.6-cycloalkyl-C.sub.3-C.sub.6-hydroxyalkenyl, C.sub.3-C.sub.6-cycloalkyl-C.sub.3-C.sub.6-hydroxyhaloalkenyl, C.sub.3-C.sub.6-halocycloalkyl-C.sub.3-C.sub.6-hydroxyalkenyl, C.sub.3-C.sub.6-halocycloalkyl-C.sub.3-C.sub.6-hydroxyhaloalkenyl, C.sub.3-C.sub.6-cycloalkenyl-C.sub.3-C.sub.6-hydroxyalkenyl, C.sub.3-C.sub.6-cycloalkenyl-C.sub.3-C.sub.6-hydroxyhaloalkenyl, C.sub.3-C.sub.6-halocycloalkenyl-C.sub.3-C.sub.6-hydroxyalkenyl, C.sub.3-C.sub.6-halocycloalkenyl-C.sub.3-C.sub.6-hydroxyhaloalkenyl, C.sub.3-C.sub.6-cycloalkyl-C.sub.3-C.sub.6-hydroxyalkynyl, C.sub.3-C.sub.6-halocycloalkyl-C.sub.3-C.sub.6-hydroxyalkynyl, C.sub.3-C.sub.6-cycloalkenyl-C.sub.3-C.sub.6-hydroxyalkynyl, C.sub.3-C.sub.6-halocycloalkenyl-C.sub.3-C.sub.6-hydroxyalkynyl, C.sub.3-C.sub.6-cycloalkyl-C.sub.2-C.sub.6-hydroxyalkylidenyl, C.sub.3-C.sub.6-halocycloalkyl-C.sub.2-C.sub.6-hydroxyalkylidenyl, C.sub.3-C.sub.6-cycloalkenyl-C.sub.2-C.sub.6-hydroxyalkylidenyl, C.sub.3-C.sub.6-halocycloalkyl-C.sub.2-C.sub.6-hydroxyalkylidenyl, heterocyclyl-C.sub.2-C.sub.6-hydroxyalkylidenyl, hydroxy-carbonyl-C.sub.1-C.sub.6-hydroxyalkyl, hydroxycarbonyl-C.sub.1-C.sub.6-alkyl, hydroxycarbonyl-C.sub.1-C.sub.6-haloalkyl, C.sub.1-C.sub.6-alkoxycarbonyl-C.sub.1-C.sub.6-hydroxyalkyl, C.sub.1-C.sub.6-haloalkoxycarbonyl-C.sub.1-C.sub.6-hydroxyalkyl, C.sub.1-C.sub.6-alkoxycarbonyl-C.sub.1-C.sub.6-haloalkyl, C.sub.1-C.sub.6-haloalkoxycarbonyl-C.sub.1-C.sub.6-haloalkyl, C.sub.1-C.sub.6-alkoxycarbonyl-C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkoxycarbonyl-C.sub.1-C.sub.6-alkyl, C.sub.3-C.sub.6-hydroxycycloalkyl-C.sub.1-C.sub.6-hydroxyalkyl, C.sub.3-C.sub.6-hydroxycycloalkenyl-C.sub.1-C.sub.6-hydroxyalkyl, C.sub.3-C.sub.6-hydroxycycloalkyl-C.sub.3-C.sub.6-hydroxyalkenyl, C.sub.3-C.sub.6-hydroxycycloalkenyl-C.sub.3-C.sub.6-hydroxyalkenyl, C.sub.3-C.sub.6-hydroxycycloalkyl-C.sub.3-C.sub.6-hydroxyalkynyl, C.sub.3-C.sub.6-hydroxycycloalkenyl-C.sub.3-C.sub.6-hydroxyalkenyl, C.sub.2-C.sub.6-dihydroxyalkyl, C.sub.3-C.sub.6-dihydroxyhaloalkyl, C.sub.4-C.sub.6-dihydroxyalkenyl, C.sub.4-C.sub.6-dihydroxyhaloalkenyl, C.sub.4-C.sub.6-dihydroxyalkynyl, C.sub.6-C.sub.6-dihydroxyhaloalkynyl, C.sub.4-C.sub.6-dihydroxycycloalkyl, C.sub.4-C.sub.6-dihydroxyhalocycloalkyl, C.sub.4-C.sub.6-dihydroxycycloalkenyl, C.sub.4-C.sub.6-dihydroxyhalocycloalkenyl, C.sub.3-C.sub.6-cycloalkyl-C.sub.2-C.sub.6-dihydroxyalkyl, C.sub.3-C.sub.6-halocycloalkyl-C.sub.2-C.sub.6-dihydroxyalkyl, C.sub.3-C.sub.6-cycloalkenyl-C.sub.2-C.sub.6-dihydroxyalkyl, C.sub.3-C.sub.6-halocycloalkenyl-C.sub.2-C.sub.6-dihydroxyalkyl, C.sub.3-C.sub.6-cycloalkyl-C.sub.3-C.sub.6-dihydroxyalkenyl, C.sub.3-C.sub.6-halocycloalkyl-C.sub.3-C.sub.6-dihydroxyalkenyl, C.sub.3-C.sub.6-cycloalkenyl-C.sub.3-C.sub.6-dihydroxyalkenyl, C.sub.3-C.sub.6-halocycloalkenyl-C.sub.3-C.sub.6-dihydroxyalkenyl, C.sub.3-C.sub.6-cycloalkyl-C.sub.4-C.sub.6-dihydroxyalkynyl, C.sub.3-C.sub.6-halocycloalkyl-C.sub.4-C.sub.6-dihydroxyalkynyl, C.sub.3-C.sub.6-cycloalkenyl-C.sub.4-C.sub.6-dihydroxyalkynyl, C.sub.3-C.sub.6-halocycloalkyl-C.sub.4-C.sub.6-dihydroxyalkynyl, C.sub.3-C.sub.6-cycloalkyl-C.sub.3-C.sub.6-dihydroxyalkylidenyl, C.sub.3-C.sub.6-halocycloalkyl-C.sub.3-C.sub.6-dihydroxyalkylidenyl, heterocyclyl-C.sub.3-C.sub.6-dihydroxyalkylidenyl, hydroxycarbonyl-C.sub.2-C.sub.6-dihydroxyalkyl, hydroxycarbonyl-C.sub.3-C.sub.6-dihydroxyhaloalkyl, C.sub.1-C.sub.6-alkoxycarbonyl-C.sub.2-C.sub.6-dihydroxyalkyl, C.sub.1-C.sub.6-haloalkoxycarbonyl-C.sub.2-C.sub.6-dihydroxyalkyl, C.sub.1-C.sub.6-haloalkoxycarbonyl-C.sub.3-C.sub.6-dihydroxyhaloalkyl, C.sub.3-C.sub.6-dihydroxycycloalkyl-C.sub.1-C.sub.6-alkyl, C.sub.3-C.sub.6-dihydroxycycloalkyl-C.sub.1-C.sub.6-haloalkyl, C.sub.3-C.sub.6-dihydroxycycloalkyl-C.sub.2-C.sub.6-alkenyl, C.sub.3-C.sub.6-dihydroxycycloalkyl-C.sub.2-C.sub.6-haloalkenyl, C.sub.3-C.sub.6-dihydroxycycloalkyl-C.sub.2-C.sub.6-alkynyl, C.sub.3-C.sub.6-dihydroxycycloalkyl-C.sub.3-C.sub.6-haloalkynyl, C.sub.1-C.sub.6-alkylcarbonyl-C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkylcarbonyl-C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-alkylcarbonyl-C.sub.1-C.sub.6-haloalkyl, C.sub.1-C.sub.6-haloalkylcarbonyl-C.sub.1-C.sub.6-haloalkyl, hydroxycarbonyl-C.sub.2-C.sub.6-alkenyl, hydroxycarbonyl-C.sub.2-C.sub.6-haloalkenyl, C.sub.1-C.sub.6-alkoxycarbonyl-C.sub.2-C.sub.6-alkenyl, C.sub.1-C.sub.6-haloalkoxycarbonyl-C.sub.2-C.sub.6-alkenyl, C.sub.1-C.sub.6-alkoxycarbonyl-C.sub.2-C.sub.6-haloalkenyl, C.sub.1-C.sub.6-haloalkoxycarbonyl-C.sub.2-C.sub.6-haloalkenyl, hydroxycarbonyl-C.sub.2-C.sub.6-alkynyl, hydroxycarbonyl-C.sub.3-C.sub.6-haloalkynyl, C.sub.1-C.sub.6-alkoxycarbonyl-C.sub.2-C.sub.6-alkynyl, C.sub.1-C.sub.6-haloalkoxycarbonyl-C.sub.2-C.sub.6-alkynyl, C.sub.1-C.sub.6-alkoxycarbonyl-C.sub.3-C.sub.6-halo-alkynyl, C.sub.1-C.sub.6-haloalkoxycarbonyl-C.sub.3-C.sub.6-haloalkynyl, C.sub.1-C.sub.6-cyanoalkyl, C.sub.2-C.sub.6-cyanohaloalkyl, C.sub.1-C.sub.6-dicyanoalkyl, C.sub.2-C.sub.6-dicyanohaloalkyl, di(hydroxycarbonyl)-C.sub.1-C.sub.6-alkyl, di(hydroxycarbonyl)-C.sub.1-C.sub.6-haloalkyl, di(C.sub.1-C.sub.6-alkoxycarbonyl)-C.sub.1-C.sub.6-alkyl, di(C.sub.1-C.sub.6-haloalkoxycarbonyl)-C.sub.1-C.sub.6-alkyl, di(C.sub.1-C.sub.6-alkoxycarbonyl)-C.sub.1-C.sub.6-haloalkyl, di(C.sub.1-C.sub.6-haloalkoxycarbonyl)-C.sub.1-C.sub.6-haloalkyl, di(C.sub.1-C.sub.6-alkoxyl)phosphoryl-C.sub.1-C.sub.6-alkyl, di(C.sub.1-C.sub.6-haloalkoxyl)phosphoryl-C.sub.1-C.sub.6-alkyl, di(C.sub.1-C.sub.6-alkoxyl)phosphoryl-C.sub.1-C.sub.6-haloalkyl, di(C.sub.1-C.sub.6-haloalkoxyl)phosphoryl-C.sub.1-C.sub.6-haloalkyl, phosphoryl-C.sub.1-C.sub.6-alkyl, phosphoryl-C.sub.1-C.sub.6-haloalkyl, di[di(C.sub.1-C.sub.6-alkoxyl)phosphoryl-)]C.sub.1-C.sub.6-alkyl, di[di(C.sub.1-C.sub.6-haloalkoxyl)phosphoryl-)]C.sub.1-C.sub.6-alkyl, di[di(C.sub.1-C.sub.6-alkoxyl)phosphoryl-)]C.sub.1-C.sub.6-haloalkyl, di[di(C.sub.1-C.sub.6-haloalkoxyl)phosphoryl-)]C.sub.1-C.sub.6-haloalkyl, diphosphoryl-C.sub.1-C.sub.6-alkyl, diphosphoryl-C.sub.1-C.sub.6-haloalkyl, C.sub.1-C.sub.6-alkylthio-C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkylthio-C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-alkylthio-C.sub.1-C.sub.6-haloalkyl, C.sub.1-C.sub.6-haloalkylthio-C.sub.1-C.sub.6-haloalkyl, C.sub.1-C.sub.6-alkylsulfinly-C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkylsulfinly-C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-alkylsulfinly-C.sub.1-C.sub.6-haloalkyl, C.sub.1-C.sub.6-haloalkylsulfinly-C.sub.1-C.sub.6-haloalkyl, C.sub.1-C.sub.6-alkylsulfonyl-C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkylsulfonyl-C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkylsulfonyl-C.sub.1-C.sub.6-haloalkyl, phenyl, 5-, 6- or 9 membered heteroaryl, 3- to 6-membered heterocyclyl, (C.sub.1-C.sub.6-alkyl)carbonylaminocarbonyl, (C.sub.2-C.sub.6-alkenyl)carbo-nylamino-carbonyl, (C.sub.3-C.sub.6-alkynyl)carbonylaminocarbonyl, (C.sub.1-C.sub.6-haloalkyl)carbo-nylaminocarbonyl, (C.sub.2-C.sub.6-haloalkenyl)carbonylaminocarbonyl, (C.sub.3-C.sub.6-haloalkynyl)car-bonylaminocarbonyl, phenylcarbonylaminocarbonyl, (C.sub.3-C.sub.6-cycloalkyl)carbonylaminocarbonyl, [(C.sub.1-C.sub.6-alkyl)amino]carbonylaminocarbonyl, or [di(C.sub.1-C.sub.6-alkyl)amino]carbonylaminocarbonyl, heterocyclylcarbonylaminocarbonyl, heteroarylcarbonylaminocarbonyl, phenylcarbonylaminocarbonyl; wherein OH groups of R.sup.2 are unsubstituted or substituted by R.sup.b; cyclic groups of R.sup.2 are unsubstituted or substituted by R.sup.c; and acyclic aliphatic groups of R.sup.2 are unsubstituted or substituted by R.sup.d; R.sup.b is C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkyl, C.sub.3-C.sub.6-alkenyl, C.sub.3-C.sub.6-haloalkenyl, C.sub.3-C.sub.6-alkynyl, C.sub.3-C.sub.6-haloalkynyl, C.sub.3-C.sub.6-cycloalkyl, C.sub.3-C.sub.6-halocycloalkyl, C.sub.4-C.sub.6-cycloalkenyl, C.sub.3-C.sub.6-halocycloalkenyl, C.sub.1-C.sub.6-alkoxycarbonyl-C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkoxycarbonyl-C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-alkoxycarbonyl-C.sub.1-C.sub.6-haloalkyl, C.sub.1-C.sub.6-haloalkoxycarbonyl-C.sub.1-C.sub.6-haloalkyl, C.sub.1-C.sub.6-alkylcarbonyl, C.sub.1-C.sub.6-haloalkylcarbonyl, hydroxycarbonyl-C.sub.1-C.sub.6-alkyl, hydroxycarbonyl-C.sub.1-C.sub.6-haloalkyl, C.sub.1-C.sub.6-alkyloxycarbonyl, C.sub.1-C.sub.6-haloalkyloxycarbonyl, C.sub.1-C.sub.6-alkylthiocarbonyl, C.sub.1-C.sub.6-haloalkylthiocarbonyl, C.sub.1-C.sub.6-alkylaminocarbonyl, C.sub.1-C.sub.6-haloalkylaminocarbonyl, C.sub.1-C.sub.6-dialkylaminocarbonyl, C.sub.1-C.sub.6-dihaloalkylaminocarbonyl, C.sub.1-C.sub.6-alkylsulfonyl, C.sub.1-C.sub.6-haloalkylsulfonyl, C.sub.1-C.sub.6-alkoxy-C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkoxy-C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-alkoxy-C.sub.1-C.sub.6-haloalkyl, C.sub.1-C.sub.6-haloalkoxy-C.sub.1-C.sub.6-haloalkyl, phenyl-C.sub.1-C.sub.6-alkyl, or phenyl-C.sub.1-C.sub.6-haloalkyl; R.sup.c is halogen, CN, NO.sub.2, C.sub.1-C.sub.6-haloalkyl, OH, C.sub.1-C.sub.6-alkoxy, C.sub.1-C.sub.6-haloalkoxy, C.sub.1-C.sub.6-alkylsulfinyl, or C.sub.1-C.sub.6-alkylsulfonyl; R.sup.d is phenyl, 5- or 6-membered heteroaryl, or 3- to 6-membered heterocyclyl; wherein the substituent R.sup.d is unsubstituted or substituted by R.sup.e; R.sup.e is halogen, CN, NO.sub.2, C.sub.1-C.sub.6-haloalkyl, OH, C.sub.1-C.sub.6-alkoxy, C.sub.1-C.sub.6-haloalkoxy, C.sub.1-C.sub.6-alkylsulfonyl; R.sup.3 is halogen, CN, NO.sub.2, C.sub.1-C.sub.6-alkylcarbonyl, C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-haloalkenyl, C.sub.2-C.sub.6-alkynyl, C.sub.2-C.sub.6-haloalkynyl, C.sub.1-C.sub.6-alkoxy, C.sub.1-C.sub.6-halo-alkoxy, C.sub.3-C.sub.6-alkenyloxy, C.sub.3-C.sub.6-haloalkenyloxy, C.sub.3-C.sub.6-alkynyloxy, C.sub.3-C.sub.6-haloalkynyloxy, C.sub.1-C.sub.6-alkoxy-C.sub.1-C.sub.6-alkoxy, hydroxycarbonyl, C.sub.1-C.sub.6-alkoxycarbonyl, C.sub.1-C.sub.6-haloalkylthio, NH.sub.2, (C.sub.1-C.sub.6-alkyl)amino, di(C.sub.1-C.sub.6-alkyl)amino, (C.sub.1-C.sub.6-alkyl)sulfinyl, (C.sub.1-C.sub.6-alkyl)sulfonyl, C.sub.3-C.sub.6-cycloalkyl, (C.sub.3-C.sub.6-cycloalkyl)oxy or phenyl; wherein the cyclic groups of R.sup.3 are unsubstituted or substituted by substituents R.sup.a; R.sup.4, R.sup.5, R.sup.6 and R.sup.7 independently of one another are H, halogen, CN, NO.sub.2, C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkyl, C.sub.1-C.sub.6-alkylcarbonyl, C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-haloalkenyl, C.sub.2-C.sub.6-alkynyl, C.sub.2-C.sub.6-haloalkynyl, C.sub.1-C.sub.6-alkoxy, C.sub.1-C.sub.6-haloalkoxy, C.sub.3-C.sub.6-alkenyloxy, C.sub.3-C.sub.6-haloalkenyloxy, C.sub.3-C.sub.6-alkynyloxy, C.sub.3-C.sub.6-haloalkynyloxy, C.sub.1-C.sub.6-alkoxy-C.sub.1-C.sub.6-alkoxy, hydroxycarbonyl, C.sub.1-C.sub.6-alkoxycarbonyl, C.sub.1-C.sub.6-alkylthio, C.sub.1-C.sub.6-haloalkylthio, NH.sub.2, (C.sub.1-C.sub.6-alkyl)amino, di(C.sub.1-C.sub.6-alkyl)amino, (C.sub.1-C.sub.6-alkyl)sulfinyl, (C.sub.1-C.sub.6-alkyl)sulfonyl, C.sub.3-C.sub.6-cycloalkyl, (C.sub.3-C.sub.6-cycloalkyl)oxy or phenyl; wherein the cyclic groups of R.sup.4 R.sup.5, R.sup.6 and R.sup.7 are unsubstituted or substituted by R.sup.a; R.sup.a is halogen, CN, NO.sub.2, C.sub.1-C.sub.6-alkoxy, or C.sub.1-C.sub.6-haloalkoxy; or an agriculturally acceptable salt, amide, ester, or thioester of the pyrimidine compound of formula (I), and B) herbicides of class b1) to b15): b1) lipid biosynthesis inhibitors; b2) acetolactate synthase inhibitors (ALS inhibitors); b3) photosynthesis inhibitors; b4) protoporphyrinogen-IX oxidase inhibitors, b5) bleacher herbicides; b6) enolpyruvyl shikimate 3-phosphate synthase inhibitors (EPSP inhibitors); b7) glutamine synthetase inhibitors; b8) 7,8-dihydropteroate synthase inhibitors (DHP inhibitors); b9) mitosis inhibitors; b10) inhibitors of the synthesis of very long chain fatty acids (VLCFA inhibitors); b11) cellulose biosynthesis inhibitors; b12) decoupler herbicides; b13) auxinic herbicides; b14) auxin transport inhibitors; and b15) other herbicides selected from the group consisting of bromobutide, chlorflurenol, chlorflurenol-methyl, cinmethylin, cumyluron, dalapon, dazomet, difenzoquat, difenzoquat-metilsulfate, dimethipin, DSMA, dymron, endothal and its salts, etobenzanid, flamprop, flamprop-isopropyl, flamprop-methyl, flamprop-M-isopropyl, flamprop-M-methyl, flurenol, flurenol-butyl, flurprimidol, fosamine, fosamine-ammonium, indanofan, indaziflam, maleic hydrazide, mefluidide, metam, methiozolin (CAS 403640-27-7), methyl azide, methyl bromide, methyl-dymron, methyl iodide, MSMA, oleic acid, oxaziclomefone, pelargonic acid, pyributicarb, quinoclamine, triaziflam, tridiphane and 6-chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinol, and its salts and esters; including their agriculturally acceptable salts or derivatives.
8. The composition according to claim 7, wherein the composition comprises at least one herbicide B selected from herbicides of class b1, b2, b3, b4, b5, b6, b9, b10, b13 and b14.
9. The composition according to claim 7, wherein the weight ratio of component A to component B is in the range of from 1:500 to 500:1.
10. A herbicidal composition comprising a herbicidally active amount of at least one compound of formula (I) or an agriculturally acceptable salt or derivative of the pyrimidine compound of formula (I) having an acidic functionality one pyrimidine compound of formula (I), ##STR00330## wherein: R.sup.1 is C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkyl, HO—C.sub.1-C.sub.6-alkyl, C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-haloalkenyl, C.sub.2-C.sub.6-alkynyl, C.sub.3-C.sub.6-haloalkynyl, C.sub.1-C.sub.6-alkoxy-C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-alkoxy, C.sub.3-C.sub.6-alkenyloxy, C.sub.3-C.sub.6-haloalkenyloxy, C.sub.3-C.sub.6-alkynyloxy, C.sub.3-C.sub.6-haloalkynyloxy, C.sub.1-C.sub.6-haloalkoxy, C.sub.3-C.sub.6-cycloalkoxy, C.sub.3-C.sub.6-halocycloalkoxy, C.sub.3-C.sub.6-cycloalkenyloxy, C.sub.3-C.sub.6-halocycloalkenyloxy, C.sub.1-C.sub.6-alkylthio, C.sub.1-C.sub.6-haloalkylthio, (C.sub.1-C.sub.6-alkyl)amino, di(C.sub.1-C.sub.6-alkyl)amino, C.sub.1-C.sub.6-alkylsulfinyl, C.sub.1-C.sub.6-alkylsulfonyl, C.sub.3-C.sub.6-cycloalkyl, C.sub.3-C.sub.6-cycloalkenyl, C.sub.3-C.sub.6-halocycloalkyl, C.sub.3-C.sub.6-halocycloalkenyl, [1-(C.sub.1-C.sub.6-alkyl)]-C.sub.3-C.sub.6-cycloalkyl, [1-(C.sub.2-C.sub.6-alkenyl)]-C.sub.3-C.sub.6-cycloalkyl, [1-(C.sub.2-C.sub.6-alkynyl)]-C.sub.3-C.sub.6-cycloalkyl, [1-(C.sub.1-C.sub.6-haloalkyl)]-C.sub.3-C.sub.6-cycloalkyl, [1-(C.sub.2-C.sub.6-haloalkenyl)]-C.sub.3-C.sub.6-cycloalkyl, [1-(C.sub.3-C.sub.6-haloalkynyl)]-C.sub.3-C.sub.6-cycloalkyl, C.sub.3-C.sub.6-cycloalkyl-C.sub.1-C.sub.6-alkyl, C.sub.3-C.sub.6-cycloalkyl-C.sub.1-C.sub.6-haloalkyl, C.sub.3-C.sub.6-cycloalkyl-C.sub.1-C.sub.6-alkoxy, C.sub.3-C.sub.6-cycloalkyl-C.sub.1-C.sub.6-haloalkoxy, phenyl, or 3- to 6-membered heterocyclyl; wherein the cyclic groups of R.sup.1 are unsubstituted or substituted by R.sup.a; R.sup.2 is C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkyl, C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-haloalkenyl, C.sub.1-C.sub.6-alkoxy-C.sub.2-C.sub.6-alkenyl, C.sub.1-C.sub.6-alkoxy-C.sub.2-C.sub.6-haloalkenyl, C.sub.1-C.sub.6-haloalkoxy-C.sub.2-C.sub.6-alkenyl, C.sub.1-C.sub.6-haloalkoxy-C.sub.2-C.sub.6-haloalkenyl, C.sub.2-C.sub.6-alkynyl, C.sub.2-C.sub.6-haloalkynyl, C.sub.1-C.sub.6-alkoxy-C.sub.2-C.sub.6-alkynyl, C.sub.1-C.sub.6-alkoxy-C.sub.3-C.sub.6-haloalkynyl, C.sub.1-C.sub.6-haloalkoxy-C.sub.2-C.sub.6-alkynyl, C.sub.1-C.sub.6-haloalkoxy-C.sub.3-C.sub.6-haloalkynyl, C.sub.3-C.sub.6-cycloalkyl, C.sub.3-C.sub.6-halocycloalkyl, C.sub.3-C.sub.6-cycloalkenyl, C.sub.3-C.sub.6-halocycloalkenyl, C.sub.3-C.sub.6-cycloalkyl-C.sub.1-C.sub.6-alkyl, C.sub.3-C.sub.6-cycloalkyl-C.sub.1-C.sub.6-haloalkyl, C.sub.3-C.sub.6-halocycloalkyl-C.sub.1-C.sub.6-alkyl, C.sub.3-C.sub.6-halocycloalkyl-C.sub.1-C.sub.6-haloalkyl, C.sub.3-C.sub.6-cycloalkenyl- C.sub.1-C.sub.6-alkyl, C.sub.3-C.sub.6-cycloalkenyl-C.sub.1-C.sub.6-haloalkyl, C.sub.3-C.sub.6-halocycloalkenyl- C.sub.1-C.sub.6-alkyl, C.sub.3-C.sub.6-halocycloalkenyl- C.sub.1-C.sub.6-haloalkyl, C.sub.3-C.sub.6-cycloalkyl-C.sub.2-C.sub.6-alkenyl, C.sub.3-C.sub.6-cycloalkyl-C.sub.2-C.sub.6-haloalkenyl, C.sub.3-C.sub.6-halocycloalkyl-C.sub.2-C.sub.6-alkenyl, C.sub.3-C.sub.6-halocycloalkyl-C.sub.2-C.sub.6-haloalkenyl, C.sub.3-C.sub.6-cycloalkenyl- C.sub.2-C.sub.6-alkenyl, C.sub.3-C.sub.6-cycloalkenyl- C.sub.2-C.sub.6-haloalkenyl, C.sub.3-C.sub.6-halocycloalkenyl- C.sub.2-C.sub.6-alkenyl, C.sub.3-C.sub.6-halocycloalkenyl- C.sub.2-C.sub.6-haloalkenyl, C.sub.3-C.sub.6-cycloalkyl-C.sub.2-C.sub.6-alkynyl, C.sub.3-C.sub.6-cycloalkyl-C.sub.3-C.sub.6-haloalkynyl, C.sub.3-C.sub.6-halocycloalkyl-C.sub.2-C.sub.6-alkynyl, C.sub.3-C.sub.6-halocycloalkyl-C.sub.3-C.sub.6-haloalkynyl, C.sub.3-C.sub.6-cycloalkenyl-C.sub.2-C.sub.6-alkynyl, C.sub.3-C.sub.6-cycloalkenyl-C.sub.3-C.sub.6-haloalkynyl, C.sub.3-C.sub.6-halocycloalkenyl-C.sub.2-C.sub.6-alkynyl, C.sub.3-C.sub.6-halocycloalkenyl-C.sub.3-C.sub.6-haloalkynyl, C.sub.3-C.sub.6-cycloalkyl-C.sub.1-C.sub.6-alkylidenyl, C.sub.3-C.sub.6-cycloalkyl-C.sub.2-C.sub.6-haloalkylidenyl, C.sub.3-C.sub.6-halocycloalkyl-C.sub.1-C.sub.6-alkylidenyl, C.sub.3-C.sub.6-halocycloalkyl-C.sub.2-C.sub.6-haloalkylidenyl, C.sub.3-C.sub.6-cycloalkenyl-C.sub.1-C.sub.6-alkylidenyl, C.sub.3-C.sub.6-cycloalkenyl-C.sub.2-C.sub.6-haloalkylidenyl, C.sub.3-C.sub.6-halocycloalkenyl-C.sub.1-C.sub.6-alkylidenyl, C.sub.3-C.sub.6-halocycloalkenyl-C.sub.2-C.sub.6-haloalkylidenyl, heterocyclyl-C.sub.1-C.sub.6-alkylidenyl, heterocyclyl-C.sub.1-C.sub.6-haloalkylidenyl, C.sub.3-C.sub.6-hydroxycycloalkyl-C.sub.1-C.sub.6-alkyl, C.sub.3-C.sub.6-hydroxycycloalkyl-C.sub.1-C.sub.6-haloalkyl, C.sub.3-C.sub.6-hydroxycycloalkenyl-C.sub.1-C.sub.6-alkyl, C.sub.3-C.sub.6-hydroxycycloalkenyl-C.sub.1-C.sub.6-haloalkyl, C.sub.1-C.sub.6-hydroxyalkyl, C.sub.2-C.sub.6-hydroxyhaloalkyl, C.sub.3-C.sub.6-hydroxyalkenyl, C.sub.3-C.sub.6-hydroxyhaloalkenyl, C.sub.3-C.sub.6-hydroxyalkynyl, C.sub.4-C.sub.6-hydroxyhaloalkynyl, C.sub.3-C.sub.6-hydroxycycloalkyl, C.sub.3-C.sub.6-hydroxyhalocycloalkyl, C.sub.3-C.sub.6-hydroxycycloalkenyl, C.sub.3-C.sub.6-hydroxyhalocycloalkenyl, C.sub.3-C.sub.6-cycloalkyl-C.sub.1-C.sub.6-hydroxyalkyl, C.sub.3-C.sub.6-cycloalkyl-C.sub.2-C.sub.6-hydroxyhaloalkyl, C.sub.3-C.sub.6-halocycloalkyl-C.sub.1-C.sub.6-hydroxyalkyl, C.sub.3-C.sub.6-halocycloalkyl-C.sub.2-C.sub.6-hydroxyhaloalkyl, C.sub.3-C.sub.6-cycloalkenyl-C.sub.1-C.sub.6-hydroxyalkyl, C.sub.3-C.sub.6-cycloalkenyl-C.sub.2-C.sub.6-hydroxyhaloalkyl, C.sub.3-C.sub.6-halocycloalkenyl-C.sub.1-C.sub.6-hydroxyalkylC.sub.3-C.sub.6-halocycloalkenyl-C.sub.2-C.sub.6-hydroxyhaloalkyl, C.sub.3-C.sub.6-cycloalkyl-C.sub.3-C.sub.6-hydroxyalkenyl, C.sub.3-C.sub.6-cycloalkyl-C.sub.3-C.sub.6-hydroxyhaloalkenyl, C.sub.3-C.sub.6-halocycloalkyl-C.sub.3-C.sub.6-hydroxyalkenyl, C.sub.3-C.sub.6-halocycloalkyl-C.sub.3-C.sub.6-hydroxyhaloalkenyl, C.sub.3-C.sub.6-cycloalkenyl-C.sub.3-C.sub.6-hydroxyalkenyl, C.sub.3-C.sub.6-cycloalkenyl-C.sub.3-C.sub.6-hydroxyhaloalkenyl, C.sub.3-C.sub.6-halocycloalkenyl-C.sub.3-C.sub.6-hydroxyalkenyl, C.sub.3-C.sub.6-halocycloalkenyl-C.sub.3-C.sub.6-hydroxyhaloalkenyl, C.sub.3-C.sub.6-cycloalkyl-C.sub.3-C.sub.6-hydroxyalkynyl, C.sub.3-C.sub.6-halocycloalkyl-C.sub.3-C.sub.6-hydroxyalkynyl, C.sub.3-C.sub.6-cycloalkenyl-C.sub.3-C.sub.6-hydroxyalkynyl, C.sub.3-C.sub.6-halocycloalkenyl-C.sub.3-C.sub.6-hydroxyalkynyl, C.sub.3-C.sub.6-cycloalkyl-C.sub.2-C.sub.6-hydroxyalkylidenyl, C.sub.3-C.sub.6-halocycloalkyl-C.sub.2-C.sub.6-hydroxyalkylidenyl, C.sub.3-C.sub.6-cycloalkenyl-C.sub.2-C.sub.6-hydroxyalkylidenyl, C.sub.3-C.sub.6-halocycloalkyl-C.sub.2-C.sub.6-hydroxyalkylidenyl, heterocyclyl-C.sub.2-C.sub.6-hydroxyalkylidenyl, hydroxy-carbonyl-C.sub.1-C.sub.6-hydroxyalkyl, hydroxycarbonyl-C.sub.1-C.sub.6-alkyl, hydroxycarbonyl-C.sub.1-C.sub.6-haloalkyl, C.sub.1-C.sub.6-alkoxycarbonyl-C.sub.1-C.sub.6-hydroxyalkyl, C.sub.1-C.sub.6-haloalkoxycarbonyl-C.sub.1-C.sub.6-hydroxyalkyl, C.sub.1-C.sub.6-alkoxycarbonyl-C.sub.1-C.sub.6-haloalkyl, C.sub.1-C.sub.6-haloalkoxycarbonyl-C.sub.1-C.sub.6-haloalkyl, C.sub.1-C.sub.6-alkoxycarbonyl-C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkoxycarbonyl-C.sub.1-C.sub.6-alkyl, C.sub.3-C.sub.6-hydroxycycloalkyl-C.sub.1-C.sub.6-hydroxyalkyl, C.sub.3-C.sub.6-hydroxycycloalkenyl-C.sub.1-C.sub.6-hydroxyalkyl, C.sub.3-C.sub.6-hydroxycycloalkyl-C.sub.3-C.sub.6-hydroxyalkenyl, C.sub.3-C.sub.6-hydroxycycloalkenyl-C.sub.3-C.sub.6-hydroxyalkenyl, C.sub.3-C.sub.6-hydroxycycloalkyl-C.sub.3-C.sub.6-hydroxyalkynyl, C.sub.3-C.sub.6-hydroxycycloalkenyl-C.sub.3-C.sub.6-hydroxyalkenyl, C.sub.2-C.sub.6-dihydroxyalkyl, C.sub.3-C.sub.6-dihydroxyhaloalkyl, C.sub.4-C.sub.6-dihydroxyalkenyl, C.sub.4-C.sub.6-dihydroxyhaloalkenyl, C.sub.4-C.sub.6-dihydroxyalkynyl, C.sub.5-C.sub.6-dihydroxyhaloalkynyl, C.sub.4-C.sub.6-dihydroxycycloalkyl, C.sub.4-C.sub.6-dihydroxyhalocycloalkyl, C.sub.4-C.sub.6-dihydroxycycloalkenyl, C.sub.4-C.sub.6-dihydroxyhalocycloalkenyl, C.sub.3-C.sub.6-cycloalkyl-C.sub.2-C.sub.6-dihydroxyalkyl, C.sub.3-C.sub.6-halocycloalkyl-C.sub.2-C.sub.6-dihydroxyalkyl, C.sub.3-C.sub.6-cycloalkenyl-C.sub.2-C.sub.6-dihydroxyalkyl, C.sub.3-C.sub.6-halocycloalkenyl-C.sub.2-C.sub.6-dihydroxyalkyl, C.sub.3-C.sub.6-cycloalkyl-C.sub.3-C.sub.6-dihydroxyalkenyl, C.sub.3-C.sub.6-halocycloalkyl-C.sub.3-C.sub.6-dihydroxyalkenyl, C.sub.3-C.sub.6-cycloalkenyl-C.sub.3-C.sub.6-dihydroxyalkenyl, C.sub.3-C.sub.6-halocycloalkenyl-C.sub.3-C.sub.6-dihydroxyalkenyl, C.sub.3-C.sub.6-cycloalkyl-C.sub.4-C.sub.6-dihydroxyalkynyl, C.sub.3-C.sub.6-halocycloalkyl-C.sub.4-C.sub.6-dihydroxyalkynyl, C.sub.3-C.sub.6-cycloalkenyl-C.sub.4-C.sub.6-dihydroxyalkynyl, C.sub.3-C.sub.6-halocycloalkyl-C.sub.4-C.sub.6-dihydroxyalkynyl, C.sub.3-C.sub.6-cycloalkyl-C.sub.3-C.sub.6-dihydroxyalkylidenyl, C.sub.3-C.sub.6-halocycloalkyl-C.sub.3-C.sub.6-dihydroxyalkylidenyl, heterocyclyl-C.sub.3-C.sub.6-dihydroxyalkylidenyl, hydroxycarbonyl-C.sub.2-C.sub.6-dihydroxyalkyl, hydroxycarbonyl-C.sub.3-C.sub.6-dihydroxyhaloalkyl, C.sub.1-C.sub.6-alkoxycarbonyl-C.sub.2-C.sub.6-dihydroxyalkyl, C.sub.1-C.sub.6-haloalkoxycarbonyl-C.sub.2-C.sub.6-dihydroxyalkyl, C.sub.1-C.sub.6-haloalkoxycarbonyl-C.sub.3-C.sub.6-dihydroxyhaloalkyl, C.sub.3-C.sub.6-dihydroxycycloalkyl-C.sub.1-C.sub.6-alkyl, C.sub.3-C.sub.6-dihydroxycycloalkyl-C.sub.1-C.sub.6-haloalkyl, C.sub.3-C.sub.6-dihydroxycycloalkyl-C.sub.2-C.sub.6-alkenyl, C.sub.3-C.sub.6-dihydroxycycloalkyl-C.sub.2-C.sub.6-haloalkenyl, C.sub.3-C.sub.6-dihydroxycycloalkyl-C.sub.2-C.sub.6-alkynyl, C.sub.3-C.sub.6-dihydroxycycloalkyl-C.sub.3-C.sub.6-haloalkynyl, C.sub.1-C.sub.6-alkylcarbonyl-C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkylcarbonyl-C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-alkylcarbonyl-C.sub.1-C.sub.6-haloalkyl, C.sub.1-C.sub.6-haloalkylcarbonyl-C.sub.1-C.sub.6-haloalkyl, hydroxycarbonyl-C.sub.2-C.sub.6-alkenyl, hydroxycarbonyl-C.sub.2-C.sub.6-haloalkenyl, C.sub.1-C.sub.6-alkoxycarbonyl-C.sub.2-C.sub.6-alkenyl, C.sub.1-C.sub.6-haloalkoxycarbonyl-C.sub.2-C.sub.6-alkenyl, C.sub.1-C.sub.6-alkoxycarbonyl-C.sub.2-C.sub.6-haloalkenyl, C.sub.1-C.sub.6-haloalkoxycarbonyl-C.sub.2-C.sub.6-haloalkenyl, hydroxycarbonyl-C.sub.2-C.sub.6-alkynyl, hydroxycarbonyl-C.sub.3-C.sub.6-haloalkynyl, C.sub.1-C.sub.6-alkoxycarbonyl-C.sub.2-C.sub.6-alkynyl, C.sub.1-C.sub.6-haloalkoxycarbonyl-C.sub.2-C.sub.6-alkynyl, C.sub.1-C.sub.6-alkoxycarbonyl-C.sub.3-C.sub.6-halo-alkynyl, C.sub.1-C.sub.6-haloalkoxycarbonyl-C.sub.3-C.sub.6-haloalkynyl, C.sub.1-C.sub.6-cyanoalkyl, C.sub.2-C.sub.6-cyanohaloalkyl, C.sub.1-C.sub.6-dicyanoalkyl, C.sub.2-C.sub.6-dicyanohaloalkyl, di(hydroxycarbonyl)-C.sub.1-C.sub.6-alkyl, di(hydroxycarbonyl)-C.sub.1-C.sub.6-haloalkyl, di(C.sub.1-C.sub.6-alkoxycarbonyl)-C.sub.1-C.sub.6-alkyl, di(C.sub.1-C.sub.6-haloalkoxycarbonyl)-C.sub.1-C.sub.6-alkyl, di(C.sub.1-C.sub.6-alkoxycarbonyl)-C.sub.1-C.sub.6-haloalkyl, di(C.sub.1-C.sub.6-haloalkoxycarbonyl)-C.sub.1-C.sub.6-haloalkyl, di(C.sub.1-C.sub.6-alkoxyl)phosphoryl-C.sub.1-C.sub.6-alkyl, di(C.sub.1-C.sub.6-haloalkoxyl)phosphoryl-C.sub.1-C.sub.6-alkyl, di(C.sub.1-C.sub.6-alkoxyl)phosphoryl-C.sub.1-C.sub.6-haloalkyl, di(C.sub.1-C.sub.6-haloalkoxyl)phosphoryl-C.sub.1-C.sub.6-haloalkyl, phosphoryl-C.sub.1-C.sub.6-alkyl, phosphoryl-C.sub.1-C.sub.6-haloalkyl, di[di(C.sub.1-C.sub.6-alkoxyl)phosphoryl-)]C.sub.1-C.sub.6-alkyl, di[di(C.sub.1-C.sub.6-haloalkoxyl)phosphoryl-)]C.sub.1-C.sub.6-alkyl, di[di(C.sub.1-C.sub.6-alkoxyl)phosphoryl-)]C.sub.1-C.sub.6-haloalkyl, di[di(C.sub.1-C.sub.6-haloalkoxyl)phosphoryl-)]C.sub.1-C.sub.6-haloalkyl, diphosphoryl-C.sub.1-C.sub.6-alkyl, diphosphoryl-C.sub.1-C.sub.6-haloalkyl, alkyl, C.sub.1-C.sub.6-haloalkylsulfinly-C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkylsulfinly-C.sub.1-C.sub.6-haloalkyl, C.sub.1-C.sub.6-haloalkylsulfonyl-C.sub.1-C.sub.6-haloalkyl, phenyl, 5-, 6- or 9 membered heteroaryl, 3- to 6-membered heterocyclyl, (C.sub.1-C.sub.6-alkyl)carbonylaminocarbonyl, (C.sub.2-C.sub.6-alkenyl)carbo-nylamino-carbonyl, (C.sub.3-C.sub.6-alkynyl)carbonylaminocarbonyl, (C.sub.1-C.sub.6-haloalkyl)carbo-nylaminocarbonyl, (C.sub.2-C.sub.6-haloalkenyl)carbonylaminocarbonyl, (C.sub.3-C.sub.6-haloalkynyl)car-bonylaminocarbonyl, phenylcarbonylaminocarbonyl, (C.sub.3-C.sub.6-cycloalkyl)carbonylaminocarbonyl, [(C.sub.1-C.sub.6-alkyl)amino]carbonylaminocarbonyl, or [di(C.sub.1-C.sub.6-alkyl)amino]carbonylaminocarbonyl, heterocyclylcarbonylaminocarbonyl, heteroarylcarbonylaminocarbonyl, phenylcarbonylaminocarbonyl; wherein OH groups of R.sup.2 are unsubstituted or substituted by R.sup.b; cyclic groups of R.sup.2 are unsubstituted or substituted by R.sup.c; and acyclic aliphatic groups of R.sup.2 are unsubstituted or substituted by R.sup.d; R.sup.b is C.sub.1-C.sub.6-alkyl, C.sub.3-C.sub.6-alkenyl, C.sub.3-C.sub.6-haloalkenyl, C.sub.3-C.sub.6-alkynyl, C.sub.3-C.sub.6-haloalkynyl, C.sub.3-C.sub.6-cycloalkyl, C.sub.3-C.sub.6-halocycloalkyl, C.sub.4-C.sub.6-cycloalkenyl, C.sub.3-C.sub.6-halocycloalkenyl, C.sub.1-C.sub.6-alkoxycarbonyl-C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkoxycarbonyl-C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-alkoxycarbonyl-C.sub.1-C.sub.6-haloalkyl, C.sub.1-C.sub.6-haloalkoxycarbonyl-C.sub.1-C.sub.6-haloalkyl, alkylcarbonyl, C.sub.1-C.sub.6-haloalkylcarbonyl, hydroxycarbonyl-C.sub.1-C.sub.6-alkyl, hydroxycarbonyl-C.sub.1-C.sub.6-haloalkyl, C.sub.1-C.sub.6-alkyloxycarbonyl, C.sub.1-C.sub.6-haloalkyloxycarbonyl, C.sub.1-C.sub.6-alkylthiocarbonyl, C.sub.1-C.sub.6-haloalkylthiocarbonyl, C.sub.1-C.sub.6-alkylaminocarbonyl, C.sub.1-C.sub.6-haloalkylaminocarbonyl, C.sub.1-C.sub.6-dialkylaminocarbonyl, C.sub.1-C.sub.6-dihaloalkylaminocarbonyl, C.sub.1-C.sub.6-alkylsulfonyl, C.sub.1-C.sub.6-haloalkylsulfonyl, C.sub.1-C.sub.6-haloalkoxy-C.sub.1-C.sub.6-haloalkyl, phenyl-C.sub.1-C.sub.6-alkyl, or phenyl-C.sub.1-C.sub.6-haloalkyl; R.sup.c is halogen, CN, NO.sub.2, C.sub.1-C.sub.6-haloalkyl, OH, C.sub.1-C.sub.6-alkoxy, C.sub.1-C.sub.6-haloalkoxy, C.sub.1-C.sub.6-alkylsulfinyl, or C.sub.1-C.sub.6-alkylsulfonyl; R.sup.d is phenyl, 5- or 6-membered heteroaryl, or 3- to 6-membered heterocyclyl; wherein the substituent R.sup.d is unsubstituted or substituted by R.sup.e; R.sup.e is halogen, CN, NO.sub.2, C.sub.1-C.sub.6-haloalkyl, OH, C.sub.1-C.sub.6-alkoxy, C.sub.1-C.sub.6-haloalkoxy, C.sub.1-C.sub.6-alkylsulfonyl; R.sup.3 is halogen, CN, NO.sub.2, C.sub.1-C.sub.6-alkylcarbonyl, C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-haloalkenyl, C.sub.2-C.sub.6-alkynyl, C.sub.2-C.sub.6-haloalkynyl, C.sub.1-C.sub.6-alkoxy, C.sub.1-C.sub.6-halo-alkoxy, C.sub.3-C.sub.6-alkenyloxy, C.sub.3-C.sub.6-haloalkenyloxy, C.sub.3-C.sub.6-alkynyloxy, C.sub.3-C.sub.6-haloalkynyloxy, C.sub.1-C.sub.6-alkoxy-C.sub.1-C.sub.6-alkoxy, hydroxycarbonyl, C.sub.1-C.sub.6-alkoxycarbonyl, C.sub.1-C.sub.6-haloalkylthio, NH.sub.2, (C.sub.1-C.sub.6-alkyl)amino, di(C.sub.1-C.sub.6-alkyl)amino, (C.sub.1-C.sub.6-alkyl)sulfinyl, (C.sub.1-C.sub.6-alkyl)sulfonyl, C.sub.3-C.sub.6-cycloalkyl, (C.sub.3-C.sub.6-cycloalkyl)oxy or phenyl; wherein the cyclic groups of R.sup.3 are unsubstituted or substituted by substituents R.sup.a; R.sup.4, R.sup.5, R.sup.6 and R.sup.7 independently of one another are H, halogen, CN, NO.sub.2, C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkyl, C.sub.1-C.sub.6-alkylcarbonyl, C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-haloalkenyl, C.sub.2-C.sub.6-alkynyl, C.sub.2-C.sub.6-haloalkynyl, C.sub.1-C.sub.6-alkoxy, C.sub.1-C.sub.6-haloalkoxy, C.sub.3-C.sub.6-alkenyloxy, C.sub.3-C.sub.6-haloalkenyloxy, C.sub.3-C.sub.6-alkynyloxy, C.sub.3-C.sub.6-haloalkynyloxy, C.sub.1-C.sub.6-alkoxy-C.sub.1-C.sub.6-alkoxy, hydroxycarbonyl, C.sub.1-C.sub.6-alkoxycarbonyl, C.sub.1-C.sub.6-haloalkylthio, NH.sub.2, (C.sub.1-C.sub.6-alkyl)amino, di(C.sub.1-C.sub.6-alkyl)amino, (C.sub.1-C.sub.6-alkyl)sulfinyl, (C.sub.1-C.sub.6-alkyl)sulfonyl, C.sub.3-C.sub.6-cycloalkyl, (C.sub.3-C.sub.6-cycloalkyl)oxy or phenyl; wherein the cyclic groups of R.sup.4 R.sup.5, R.sup.6 and R.sup.7 are unsubstituted or substituted by R.sup.a; R.sup.a is halogen, CN, NO.sub.2, C.sub.1-C.sub.6-alkoxy, or C.sub.6-haloalkoxy; or an agriculturally acceptable salt, amide, ester, or thioester of the pyrimidine compound of formula (I), and at least one inert liquid and/or solid carrier and, if appropriate, at least one surface-active substance.
11. A composition comprising the composition according to claim 10, further comprising a safener.
12. A method of controlling undesired vegetation, which comprises allowing a herbicidal active amount of at least one pyrimidine compound of formula (I), ##STR00331## wherein: R.sup.1 is C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkyl, HO—C.sub.1-C.sub.6-alkyl, C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-haloalkenyl, C.sub.2-C.sub.6-alkynyl, C.sub.3-C.sub.6-haloalkynyl, C.sub.1-C.sub.6-alkoxy-C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-alkoxy, C.sub.3-C.sub.6-alkenyloxy, C.sub.3-C.sub.6-haloalkenyloxy, C.sub.3-C.sub.6-alkynyloxy, C.sub.3-C.sub.6-haloalkynyloxy, C.sub.1-C.sub.6-haloalkoxy, C.sub.3-C.sub.6-cycloalkoxy, C.sub.3-C.sub.6-halocycloalkoxy, C.sub.3-C.sub.6-cycloalkenyloxy, C.sub.3-C.sub.6-halocycloalkenyloxy, C.sub.1-C.sub.6-alkylthio, C.sub.1-C.sub.6-haloalkylthio, (C.sub.1-C.sub.6-alkyl)amino, di(C.sub.1-C.sub.6-alkyl)amino, C.sub.1-C.sub.6-alkylsulfinyl, C.sub.1-C.sub.6-alkylsulfonyl, C.sub.3-C.sub.6-cycloalkyl, C.sub.3-C.sub.6-cycloalkenyl, C.sub.3-C.sub.6-halocycloalkyl, C.sub.3-C.sub.6-halocycloalkenyl, [1-(C.sub.1-C.sub.6-alkyl)]-C.sub.3-C.sub.6-cycloalkyl, [1-(C.sub.2-C.sub.6-alkenyl)]-C.sub.3-C.sub.6-cycloalkyl, [1-(C.sub.2-C.sub.6-alkynyl)]-C.sub.3-C.sub.6-cycloalkyl, [1-(C.sub.1-C.sub.6-haloalkyl)]-C.sub.3-C.sub.6-cycloalkyl, [1-(C.sub.2-C.sub.6-haloalkenyl)]-C.sub.3-C.sub.6-cycloalkyl, [1-(C.sub.3-C.sub.6-haloalkynyl)]-C.sub.3-C.sub.6-cycloalkyl, C.sub.3-C.sub.6-cycloalkyl-C.sub.1-C.sub.6-alkyl, C.sub.3-C.sub.6-cycloalkyl-C.sub.1-C.sub.6-haloalkyl, C.sub.3-C.sub.6-cycloalkyl-C.sub.1-C.sub.6-alkoxy, C.sub.3-C.sub.6-cycloalkyl-C.sub.1-C.sub.6-haloalkoxy, phenyl, or 3- to 6-membered heterocyclyl; wherein the cyclic groups of R.sup.1 are unsubstituted or substituted by R.sup.a; R.sup.2 is C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkyl, C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-haloalkenyl, C.sub.1-C.sub.6-alkoxy-C.sub.2-C.sub.6-alkenyl, C.sub.1-C.sub.6-alkoxy-C.sub.2-C.sub.6-haloalkenyl, C.sub.1-C.sub.6-haloalkoxy-C.sub.2-C.sub.6-alkenyl, C.sub.1-C.sub.6-haloalkoxy-C.sub.2-C.sub.6-haloalkenyl, C.sub.2-C.sub.6-alkynyl, C.sub.2-C.sub.6-haloalkynyl, C.sub.1-C.sub.6-alkoxy-C.sub.2-C.sub.6-alkynyl, C.sub.1-C.sub.6-alkoxy-C.sub.3-C.sub.6-haloalkynyl, C.sub.1-C.sub.6-haloalkoxy-C.sub.2-C.sub.6-alkynyl, C.sub.1-C.sub.6-haloalkoxy-C.sub.3-C.sub.6-haloalkynyl, C.sub.3-C.sub.6-cycloalkyl, C.sub.3-C.sub.6-halocycloalkyl, C.sub.3-C.sub.6-cycloalkenyl, C.sub.3-C.sub.6-halocycloalkenyl, C.sub.3-C.sub.6-cycloalkyl-C.sub.1-C.sub.6-alkyl, C.sub.3-C.sub.6-cycloalkyl-C.sub.1-C.sub.6-haloalkyl, C.sub.3-C.sub.6-halocycloalkyl-C.sub.1-C.sub.6-alkyl, C.sub.3-C.sub.6-halocycloalkyl-C.sub.1-C.sub.6-haloalkyl, C.sub.3-C.sub.6-cycloalkenyl- C.sub.1-C.sub.6-alkyl, C.sub.3-C.sub.6-cycloalkenyl-C.sub.1-C.sub.6-haloalkyl, C.sub.3-C.sub.6-halocycloalkenyl- C.sub.1-C.sub.6-alkyl, C.sub.3-C.sub.6-halocycloalkenyl- C.sub.1-C.sub.6-haloalkyl, C.sub.3-C.sub.6-cycloalkyl-C.sub.2-C.sub.6-alkenyl, C.sub.3-C.sub.6-cycloalkyl-C.sub.2-C.sub.6-haloalkenyl, C.sub.3-C.sub.6-halocycloalkyl-C.sub.2-C.sub.6-alkenyl, C.sub.3-C.sub.6-halocycloalkyl-C.sub.2-C.sub.6-haloalkenyl, C.sub.3-C.sub.6-cycloalkenyl- C.sub.2-C.sub.6-alkenyl, C.sub.3-C.sub.6-cycloalkenyl- C.sub.2-C.sub.6-haloalkenyl, C.sub.3-C.sub.6-halocycloalkenyl- C.sub.2-C.sub.6-alkenyl, C.sub.3-C.sub.6-halocycloalkenyl- C.sub.2-C.sub.6-haloalkenyl, C.sub.3-C.sub.6-cycloalkyl-C.sub.2-C.sub.6-alkynyl, C.sub.3-C.sub.6-cycloalkyl-C.sub.3-C.sub.6-haloalkynyl, C.sub.3-C.sub.6-halocycloalkyl-C.sub.2-C.sub.6-alkynyl, C.sub.3-C.sub.6-halocycloalkyl-C.sub.3-C.sub.6-haloalkynyl, C.sub.3-C.sub.6-cycloalkenyl-C.sub.2-C.sub.6-alkynyl, C.sub.3-C.sub.6-cycloalkenyl-C.sub.3-C.sub.6-haloalkynyl, C.sub.3-C.sub.6-halocycloalkenyl-C.sub.2-C.sub.6-alkynyl, C.sub.3-C.sub.6-halocycloalkenyl-C.sub.3-C.sub.6-haloalkynyl, C.sub.3-C.sub.6-cycloalkyl-C.sub.1-C.sub.6-alkylidenyl, C.sub.3-C.sub.6-cycloalkyl-C.sub.2-C.sub.6-haloalkylidenyl, C.sub.3-C.sub.6-halocycloalkyl-C.sub.1-C.sub.6-alkylidenyl, C.sub.3-C.sub.6-halocycloalkyl-C.sub.2-C.sub.6-haloalkylidenyl, C.sub.3-C.sub.6-cycloalkenyl-C.sub.1-C.sub.6-alkylidenyl, C.sub.3-C.sub.6-cycloalkenyl-C.sub.2-C.sub.6-haloalkylidenyl, C.sub.3-C.sub.6-halocycloalkenyl-C.sub.1-C.sub.6-alkylidenyl, C.sub.3-C.sub.6-halocycloalkenyl-C.sub.2-C.sub.6-haloalkylidenyl, heterocyclyl-C.sub.1-C.sub.6-alkylidenyl, heterocyclyl-C.sub.1-C.sub.6-haloalkylidenyl, C.sub.3-C.sub.6-hydroxycycloalkyl-C.sub.1-C.sub.6-alkyl, C.sub.3-C.sub.6-hydroxycycloalkyl-C.sub.1-C.sub.6-haloalkyl, C.sub.3-C.sub.6-hydroxycycloalkenyl-C.sub.1-C.sub.6-alkyl, C.sub.3-C.sub.6-hydroxycycloalkenyl-C.sub.1-C.sub.6-haloalkyl, C.sub.1-C.sub.6-hydroxyalkyl, C.sub.2-C.sub.6-hydroxyhaloalkyl, C.sub.3-C.sub.6-hydroxyalkenyl, C.sub.3-C.sub.6-hydroxyhaloalkenyl, C.sub.3-C.sub.6-hydroxyalkynyl, C.sub.4-C.sub.6-hydroxyhaloalkynyl, C.sub.3-C.sub.6-hydroxycycloalkyl, C.sub.3-C.sub.6-hydroxyhalocycloalkyl, C.sub.3-C.sub.6-hydroxycycloalkenyl, C.sub.3-C.sub.6-hydroxyhalocycloalkenyl, C.sub.3-C.sub.6-cycloalkyl-C.sub.1-C.sub.6-hydroxyalkyl, C.sub.3-C.sub.6-cycloalkyl-C.sub.2-C.sub.6-hydroxyhaloalkyl, C.sub.3-C.sub.6-halocycloalkyl-C.sub.1-C.sub.6-hydroxyalkyl, C.sub.3-C.sub.6-halocycloalkyl-C.sub.2-C.sub.6-hydroxyhaloalkyl, C.sub.3-C.sub.6-cycloalkenyl-C.sub.1-C.sub.6-hydroxyalkyl, C.sub.3-C.sub.6-cycloalkenyl-C.sub.2-C.sub.6-hydroxyhaloalkyl, C.sub.3-C.sub.6-halocycloalkenyl-C.sub.1-C.sub.6-hydroxyalkylC.sub.3-C.sub.6-halocycloalkenyl-C.sub.2-C.sub.6-hydroxyhaloalkyl, C.sub.3-C.sub.6-cycloalkyl-C.sub.3-C.sub.6-hydroxyalkenyl, C.sub.3-C.sub.6-cycloalkyl-C.sub.3-C.sub.6-hydroxyhaloalkenyl, C.sub.3-C.sub.6-halocycloalkyl-C.sub.3-C.sub.6-hydroxyalkenyl, C.sub.3-C.sub.6-halocycloalkyl-C.sub.3-C.sub.6-hydroxyhaloalkenyl, C.sub.3-C.sub.6-cycloalkenyl-C.sub.3-C.sub.6-hydroxyalkenyl, C.sub.3-C.sub.6-cycloalkenyl-C.sub.3-C.sub.6-hydroxyhaloalkenyl, C.sub.3-C.sub.6-halocycloalkenyl-C.sub.3-C.sub.6-hydroxyalkenyl, C.sub.3-C.sub.6-halocycloalkenyl-C.sub.3-C.sub.6-hydroxyhaloalkenyl, C.sub.3-C.sub.6-cycloalkyl-C.sub.3-C.sub.6-hydroxyalkynyl, C.sub.3-C.sub.6-halocycloalkyl-C.sub.3-C.sub.6-hydroxyalkynyl, C.sub.3-C.sub.6-cycloalkenyl-C.sub.3-C.sub.6-hydroxyalkynyl, C.sub.3-C.sub.6-halocycloalkenyl-C.sub.3-C.sub.6-hydroxyalkynyl, C.sub.3-C.sub.6-cycloalkyl-C.sub.2-C.sub.6-hydroxyalkylidenyl, C.sub.3-C.sub.6-halocycloalkyl-C.sub.2-C.sub.6-hydroxyalkylidenyl, C.sub.3-C.sub.6-cycloalkenyl-C.sub.2-C.sub.6-hydroxyalkylidenyl, C.sub.3-C.sub.6-halocycloalkyl-C.sub.2-C.sub.6-hydroxyalkylidenyl, heterocyclyl-C.sub.2-C.sub.6-hydroxyalkylidenyl, hydroxy-carbonyl-C.sub.1-C.sub.6-hydroxyalkyl, hydroxycarbonyl-C.sub.1-C.sub.6-alkyl, hydroxycarbonyl-C.sub.1-C.sub.6-haloalkyl, C.sub.1-C.sub.6-alkoxycarbonyl-C.sub.1-C.sub.6-hydroxyalkyl, C.sub.1-C.sub.6-haloalkoxycarbonyl-C.sub.1-C.sub.6-hydroxyalkyl, C.sub.1-C.sub.6-alkoxycarbonyl-C.sub.1-C.sub.6-haloalkyl, C.sub.1-C.sub.6-haloalkoxycarbonyl-C.sub.1-C.sub.6-haloalkyl, C.sub.1-C.sub.6-alkoxycarbonyl-C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkoxycarbonyl-C.sub.1-C.sub.6-alkyl, C.sub.3-C.sub.6-hydroxycycloalkyl-C.sub.1-C.sub.6-hydroxyalkyl, C.sub.3-C.sub.6-hydroxycycloalkenyl-C.sub.1-C.sub.6-hydroxyalkyl, C.sub.3-C.sub.6-hydroxycycloalkyl-C.sub.3-C.sub.6-hydroxyalkenyl, C.sub.3-C.sub.6-hydroxycycloalkenyl-C.sub.3-C.sub.6-hydroxyalkenyl, C.sub.3-C.sub.6-hydroxycycloalkyl-C.sub.3-C.sub.6-hydroxyalkynyl, C.sub.3-C.sub.6-hydroxycycloalkenyl-C.sub.3-C.sub.6-hydroxyalkenyl, C.sub.2-C.sub.6-dihydroxyalkyl, C.sub.3-C.sub.6-dihydroxyhaloalkyl, C.sub.4-C.sub.6-dihydroxyalkenyl, C.sub.4-C.sub.6-dihydroxyhaloalkenyl, C.sub.4-C.sub.6-dihydroxyalkynyl, C.sub.5-C.sub.6-dihydroxyhaloalkynyl, C.sub.4-C.sub.6-dihydroxycycloalkyl, C.sub.4-C.sub.6-dihydroxyhalocycloalkyl, C.sub.4-C.sub.6-dihydroxycycloalkenyl, C.sub.4-C.sub.6-dihydroxyhalocycloalkenyl, C.sub.3-C.sub.6-cycloalkyl-C.sub.2-C.sub.6-dihydroxyalkyl, C.sub.3-C.sub.6-halocycloalkyl-C.sub.2-C.sub.6-dihydroxyalkyl, C.sub.3-C.sub.6-cycloalkenyl-C.sub.2-C.sub.6-dihydroxyalkyl, C.sub.3-C.sub.6-halocycloalkenyl-C.sub.2-C.sub.6-dihydroxyalkyl, C.sub.3-C.sub.6-cycloalkyl-C.sub.3-C.sub.6-dihydroxyalkenyl, C.sub.3-C.sub.6-halocycloalkyl-C.sub.3-C.sub.6-dihydroxyalkenyl, C.sub.3-C.sub.6-cycloalkenyl-C.sub.3-C.sub.6-dihydroxyalkenyl, C.sub.3-C.sub.6-halocycloalkenyl-C.sub.3-C.sub.6-dihydroxyalkenyl, C.sub.3-C.sub.6-cycloalkyl-C.sub.4-C.sub.6-dihydroxyalkynyl, C.sub.3-C.sub.6-halocycloalkyl-C.sub.4-C.sub.6-dihydroxyalkynyl, C.sub.3-C.sub.6-cycloalkenyl-C.sub.4-C.sub.6-dihydroxyalkynyl, C.sub.3-C.sub.6-halocycloalkyl-C.sub.4-C.sub.6-dihydroxyalkynyl, C.sub.3-C.sub.6-cycloalkyl-C.sub.3-C.sub.6-dihydroxyalkylidenyl, C.sub.3-C.sub.6-halocycloalkyl-C.sub.3-C.sub.6-dihydroxyalkylidenyl, heterocyclyl-C.sub.3-C.sub.6-dihydroxyalkylidenyl, hydroxycarbonyl-C.sub.2-C.sub.6-dihydroxyalkyl, hydroxycarbonyl-C.sub.3-C.sub.6-dihydroxyhaloalkyl, C.sub.1-C.sub.6-alkoxycarbonyl-C.sub.2-C.sub.6-dihydroxyalkyl, C.sub.1-C.sub.6-haloalkoxycarbonyl-C.sub.2-C.sub.6-dihydroxyalkyl, C.sub.1-C.sub.6-haloalkoxycarbonyl-C.sub.3-C.sub.6-dihydroxyhaloalkyl, C.sub.3-C.sub.6-dihydroxycycloalkyl-C.sub.1-C.sub.6-alkyl, C.sub.3-C.sub.6-dihydroxycycloalkyl-C.sub.1-C.sub.6-haloalkyl, C.sub.3-C.sub.6-dihydroxycycloalkyl-C.sub.2-C.sub.6-alkenyl, C.sub.3-C.sub.6-dihydroxycycloalkyl-C.sub.2-C.sub.6-haloalkenyl, C.sub.3-C.sub.6-dihydroxycycloalkyl-C.sub.2-C.sub.6-alkynyl, C.sub.3-C.sub.6-dihydroxycycloalkyl-C.sub.3-C.sub.6-haloalkynyl, C.sub.1-C.sub.6-alkylcarbonyl-C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkylcarbonyl-C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-alkylcarbonyl-C.sub.1-C.sub.6-haloalkyl, C.sub.1-C.sub.6-haloalkylcarbonyl-C.sub.1-C.sub.6-haloalkyl, hydroxycarbonyl-C.sub.2-C.sub.6-alkenyl, hydroxycarbonyl-C.sub.2-C.sub.6-haloalkenyl, C.sub.1-C.sub.6-alkoxycarbonyl-C.sub.2-C.sub.6-alkenyl, C.sub.1-C.sub.6-haloalkoxycarbonyl-C.sub.2-C.sub.6-alkenyl, C.sub.1-C.sub.6-alkoxycarbonyl-C.sub.2-C.sub.6-haloalkenyl, C.sub.1-C.sub.6-haloalkoxycarbonyl-C.sub.2-C.sub.6-haloalkenyl, hydroxycarbonyl-C.sub.2-C.sub.6-alkynyl, hydroxycarbonyl-C.sub.3-C.sub.6-haloalkynyl, C.sub.1-C.sub.6-alkoxycarbonyl-C.sub.2-C.sub.6-alkynyl, C.sub.1-C.sub.6-haloalkoxycarbonyl-C.sub.2-C.sub.6-alkynyl, C.sub.1-C.sub.6-alkoxycarbonyl-C.sub.3-C.sub.6-halo-alkynyl, C.sub.1-C.sub.6-haloalkoxycarbonyl-C.sub.3-C.sub.6-haloalkynyl, C.sub.1-C.sub.6-cyanoalkyl, C.sub.2-C.sub.6-cyanohaloalkyl, C.sub.1-C.sub.6-dicyanoalkyl, C.sub.2-C.sub.6-dicyanohaloalkyl, di(hydroxycarbonyl)-C.sub.1-C.sub.6-alkyl, di(hydroxycarbonyl)-C.sub.1-C.sub.6-haloalkyl, di(C.sub.1-C.sub.6-alkoxycarbonyl)-C.sub.1-C.sub.6-alkyl, di(C.sub.1-C.sub.6-haloalkoxycarbonyl)-C.sub.1-C.sub.6-alkyl, di(C.sub.1-C.sub.6-alkoxycarbonyl)-C.sub.1-C.sub.6-haloalkyl, di(C.sub.1-C.sub.6-haloalkoxycarbonyl)-C.sub.1-C.sub.6-haloalkyl, di(C.sub.1-C.sub.6-alkoxyl)phosphoryl-C.sub.1-C.sub.6-alkyl, di(C.sub.1-C.sub.6-haloalkoxyl)phosphoryl-C.sub.1-C.sub.6-alkyl, di(C.sub.1-C.sub.6-alkoxyl)phosphoryl-C.sub.1-C.sub.6-haloalkyl, di(C.sub.1-C.sub.6-haloalkoxyl)phosphoryl-C.sub.1-C.sub.6-haloalkyl, phosphoryl-C.sub.1-C.sub.6-alkyl, phosphoryl-C.sub.1-C.sub.6-haloalkyl, di[di(C.sub.1-C.sub.6-alkoxyl)phosphoryl-)]C.sub.1-C.sub.6-alkyl, di[di(C.sub.1-C.sub.6-haloalkoxyl)phosphoryl-)]C.sub.1-C.sub.6-alkyl, di[di(C.sub.1-C.sub.6-alkoxyl)phosphoryl-)]C.sub.1-C.sub.6-haloalkyl, di[di(C.sub.1-C.sub.6-haloalkoxyl)phosphoryl-)]C.sub.1-C.sub.6-haloalkyl, diphosphoryl-C.sub.1-C.sub.6-alkyl, diphosphoryl-C.sub.1-C.sub.6-haloalkyl, C.sub.1-C.sub.6-alkylthio-C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkylthio-C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-alkylthio-C.sub.1-C.sub.6-haloalkyl, C.sub.1-C.sub.6-haloalkylthio-C.sub.1-C.sub.6-haloalkyl, C.sub.1-C.sub.6-alkylsulfinly-C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkylsulfinly-C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-alkylsulfinly-C.sub.1-C.sub.6-haloalkyl, C.sub.1-C.sub.6-haloalkylsulfinly-C.sub.1-C.sub.6-haloalkyl, C.sub.1-C.sub.6-alkylsulfonyl-C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkylsulfonyl-C.sub.1-C.sub.6-haloalkyl, phenyl, 5-, 6- or 9 membered heteroaryl, 3- to 6-membered heterocyclyl, (C.sub.1-C.sub.6-alkyl)carbonylaminocarbonyl, (C.sub.2-C.sub.6-alkenyl)carbo-nylamino-carbonyl, (C.sub.3-C.sub.6-alkynyl)carbonylaminocarbonyl, (C.sub.1-C.sub.6-haloalkyl)carbo-nylaminocarbonyl, (C.sub.2-C.sub.6-haloalkenyl)carbonylaminocarbonyl, (C.sub.3-C.sub.6-haloalkynyl)car-bonylaminocarbonyl, phenylcarbonylaminocarbonyl, (C.sub.3-C.sub.6-cycloalkyl)carbonylaminocarbonyl, [(C.sub.1-C.sub.6-alkyl)amino]carbonylaminocarbonyl, or [di(C.sub.1-C.sub.6-alkyl)amino]carbonylaminocarbonyl, heterocyclylcarbonylaminocarbonyl, heteroarylcarbonylaminocarbonyl, phenylcarbonylaminocarbonyl; wherein OH groups of R.sup.2 are unsubstituted or substituted by R.sup.b; cyclic groups of R.sup.2 are unsubstituted or substituted by R.sup.c; and acyclic aliphatic groups of R.sup.2 are unsubstituted or substituted by R.sup.d; R.sup.b is C.sub.1-C.sub.6-alkyl, C.sub.3-C.sub.6-alkenyl, C.sub.3-C.sub.6-haloalkenyl, C.sub.3-C.sub.6-alkynyl, C.sub.3-C.sub.6-haloalkynyl, C.sub.3-C.sub.6-cycloalkyl, C.sub.3-C.sub.6-halocycloalkyl, C.sub.4-C.sub.6-cycloalkenyl, C.sub.3-C.sub.6-halocycloalkenyl, C.sub.1-C.sub.6-alkoxycarbonyl-C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkoxycarbonyl-C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-alkoxycarbonyl-C.sub.1-C.sub.6-haloalkyl, C.sub.1-C.sub.6-haloalkoxycarbonyl-C.sub.1-C.sub.6-haloalkyl, C.sub.1-C.sub.6-alkylcarbonyl, C.sub.1-C.sub.6-haloalkylcarbonyl, hydroxycarbonyl-C.sub.1-C.sub.6-alkyl, hydroxycarbonyl-C.sub.1-C.sub.6-haloalkyl, C.sub.1-C.sub.6-alkyloxycarbonyl, C.sub.1-C.sub.6-haloalkyloxycarbonyl, C.sub.1-C.sub.6-alkylthiocarbonyl, C.sub.1-C.sub.6-haloalkylthiocarbonyl, C.sub.1-C.sub.6-alkylaminocarbonyl, C.sub.1-C.sub.6-haloalkylaminocarbonyl, C.sub.1-C.sub.6-dialkylaminocarbonyl, C.sub.1-C.sub.6-dihaloalkylaminocarbonyl, C.sub.1-C.sub.6-alkylsulfonyl, C.sub.1-C.sub.6-haloalkylsulfonyl, C.sub.1-C.sub.6-haloalkoxy-C.sub.1-C.sub.6-haloalkyl, phenyl-C.sub.1-C.sub.6-alkyl, or phenyl-C.sub.1-C.sub.6-haloalkyl; R.sup.c is halogen, CN, NO.sub.2, C.sub.1-C.sub.6-haloalkyl, OH, C.sub.1-C.sub.6-alkoxy, C.sub.1-C.sub.6-haloalkoxy, C.sub.1-C.sub.6-alkylsulfinyl, or C.sub.1-C.sub.6-alkylsulfonyl; R.sup.d is phenyl, 5- or 6-membered heteroaryl, or 3- to 6-membered heterocyclyl; wherein the substituent R.sup.d is unsubstituted or substituted by R.sup.e; R.sup.e is halogen, CN, NO.sub.2, C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkyl, OH, C.sub.1-C.sub.6-alkoxy, C.sub.1-C.sub.6-haloalkoxy, C.sub.1-C.sub.6-alkylsulfonyl; R.sup.3 is halogen, CN, NO.sub.2, C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkyl, C.sub.1-C.sub.6-alkylcarbonyl, C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-haloalkenyl, C.sub.2-C.sub.6-alkynyl, C.sub.2-C.sub.6-haloalkynyl, C.sub.1-C.sub.6-alkoxy, C.sub.1-C.sub.6-halo-alkoxy, C.sub.3-C.sub.6-alkenyloxy, C.sub.3-C.sub.6-haloalkenyloxy, C.sub.3-C.sub.6-alkynyloxy, C.sub.3-C.sub.6-haloalkynyloxy, C.sub.1-C.sub.6-alkoxy-C.sub.1-C.sub.6-alkoxy, hydroxycarbonyl, C.sub.1-C.sub.6-alkoxycarbonyl, C.sub.1-C.sub.6-haloalkylthio, NH.sub.2, (C.sub.1-C.sub.6-alkyl)amino, di(C.sub.1-C.sub.6-alkyl)amino, (C.sub.1-C.sub.6-alkyl)sulfinyl, (C.sub.1-C.sub.6-alkyl)sulfonyl, C.sub.3-C.sub.6-cycloalkyl, (C.sub.3-C.sub.6-cycloalkyl)oxy or phenyl; wherein the cyclic groups of R.sup.3 are unsubstituted or substituted by substituents R.sup.a; R.sup.4, R.sup.5, R.sup.6 and R.sup.7 independently of one another are H, halogen, CN, NO.sub.2, C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkyl, C.sub.1-C.sub.6-alkylcarbonyl, C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-haloalkenyl, C.sub.2-C.sub.6-alkynyl, C.sub.2-C.sub.6-haloalkynyl, C.sub.1-C.sub.6-alkoxy, C.sub.1-C.sub.6-haloalkoxy, C.sub.3-C.sub.6-alkenyloxy, C.sub.3-C.sub.6-haloalkenyloxy, C.sub.3-C.sub.6-alkynyloxy, C.sub.3-C.sub.6-haloalkynyloxy, C.sub.1-C.sub.6-alkoxy-C.sub.1-C.sub.6-alkoxy, hydroxycarbonyl, C.sub.1-C.sub.6-alkoxycarbonyl, C.sub.1-C.sub.6-alkylthio, C.sub.1-C.sub.6-haloalkylthio, NH.sub.2, (C.sub.1-C.sub.6-alkyl)amino, di(C.sub.1-C.sub.6-alkyl)amino, (C.sub.1-C.sub.6-alkyl)sulfinyl, (C.sub.1-C.sub.6-alkyl)sulfonyl, C.sub.3-C.sub.6-cycloalkyl, (C.sub.3-C.sub.6-cycloalkyl)oxy or phenyl; wherein the cyclic groups of R.sup.4 R.sup.5, R.sup.6 and R.sup.7 are unsubstituted or substituted by R.sup.a; R.sup.a is halogen, CN, NO.sub.2, C.sub.1-C.sub.6-haloalkyl, C.sub.1-C.sub.6-alkoxy, or C.sub.1-C.sub.6-haloalkoxy; or an agriculturally acceptable salt, amide, ester, or thioester of the pyrimidine compound of formula (I), to act on plants, their environment or on seed.
13. The method of claim 12, wherein R.sup.1 is C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-alkoxy, C.sub.1-C.sub.6-haloalkoxy, C.sub.3-C.sub.6-alkenyloxy, C.sub.3-C.sub.6-haloalkenyloxy, C.sub.3-C.sub.6-alkynyloxy, C.sub.4-C.sub.6-haloalkynyloxy, C.sub.1-C.sub.6-alkylthio, or C.sub.3-C.sub.6-cycloalkyl, wherein the cycloalkyl substituent is unsubstituted; R.sup.2 is C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-haloalkenyl, C.sub.1-C.sub.6-alkoxy-C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-alkynyl, C.sub.3-C.sub.6-cycloalkenyl, C.sub.3-C.sub.6-cycloalkenyl-C.sub.1-C.sub.6-alkyl, C.sub.3-C.sub.6-cycloalkyl-C.sub.1-C.sub.6-alkylidenyl, C.sub.3-C.sub.6-halocycloalkyl-C.sub.1-C.sub.6-alkylidenyl, C.sub.3-C.sub.6-cycloalkenyl-C.sub.1-C.sub.6-alkylidenyl, C.sub.3-C.sub.6-hydroxycycloalkyl-C.sub.1-C.sub.6-alkyl, C.sub.3-C.sub.6-hydroxycycloalkenyl-C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-hydroxyalkyl, C.sub.3-C.sub.6-cycloalkyl-C.sub.2-C.sub.6-hydroxyalkylidenyl, hydroxycarbonyl-C.sub.1-C.sub.6-alkyl, hydroxycarbonyl-C.sub.1-C.sub.6-haloalkyl, C.sub.1-C.sub.6-alkoxycarbonyl-C.sub.1-C.sub.6-alkyl, C.sub.3-C.sub.6-hydroxycycloalkyl-C.sub.1-C.sub.6-hydroxyalkyl, C.sub.2-C.sub.6-dihydroxyalkyl, C.sub.3-C.sub.6-cycloalkyl-C.sub.3-C.sub.6-dihydroxyalkylidenyl, hydroxycarbonyl-C.sub.2-C.sub.6-dihydroxyalkyl, C.sub.1-C.sub.6-alkoxycarbonyl-C.sub.2-C.sub.6-dihydroxyalkyl, C.sub.1-C.sub.6-dicyanoalkyl, 5- or 6-membered heteroaryl, or (C.sub.1-C.sub.6-alkyl)carbonylaminocarbonyl; wherein OH groups of R.sup.2 are unsubstituted or substituted by R.sup.b, cyclic groups of R.sup.2 are unsubstituted or substituted by R.sup.c, and acyclic aliphatic groups of R.sup.2 are unsubstituted or substituted by R.sup.d; R.sup.b is C.sub.1-C.sub.6-alkyl, C.sub.3-C.sub.6-alkenyl, C.sub.3-C.sub.6-haloalkenyl, C.sub.3-C.sub.6-alkynyl, C.sub.3-C.sub.6-haloalkynyl, C.sub.3-C.sub.6-cycloalkyl, C.sub.3-C.sub.6-halocycloalkyl, C.sub.4-C.sub.6-cycloalkenyl, C.sub.3-C.sub.6-halocycloalkenyl, C.sub.1-C.sub.6-alkoxycarbonyl-C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkoxycarbonyl-C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-alkoxycarbonyl-C.sub.1-C.sub.6-haloalkyl, C.sub.1-C.sub.6-haloalkoxycarbonyl-C.sub.1-C.sub.6-haloalkyl, C.sub.1-C.sub.6-alkylcarbonyl, C.sub.1-C.sub.6-haloalkylcarbonyl, hydroxycarbonyl-C.sub.1-C.sub.6-alkyl, hydroxycarbonyl-C.sub.1-C.sub.6-haloalkyl, C.sub.1-C.sub.6-alkyloxycarbonyl, C.sub.1-C.sub.6-haloalkyloxycarbonyl, C.sub.1-C.sub.6-alkylthiocarbonyl, C.sub.1-C.sub.6-haloalkylthiocarbonyl, C.sub.1-C.sub.6-alkylaminocarbonyl, C.sub.1-C.sub.6-haloalkylaminocarbonyl, C.sub.1-C.sub.6-dialkylaminocarbonyl, C.sub.1-C.sub.6-dihaloalkylaminocarbonyl, C.sub.1-C.sub.6-alkylsulfonyl, C.sub.1-C.sub.6-haloalkylsulfonyl, C.sub.1-C.sub.6-haloalkoxy-C.sub.1-C.sub.6-haloalkyl, phenyl-C.sub.1-C.sub.6-alkyl, or phenyl-C.sub.1-C.sub.6-haloalkyl; R.sup.c is halogen, CN, NO.sub.2, C.sub.1-C.sub.6-haloalkyl, OH, C.sub.1-C.sub.6-alkoxy, C.sub.1-C.sub.6-haloalkoxy, C.sub.1-C.sub.6-alkylsulfinyl, or C.sub.1-C.sub.6-alkylsulfonyl; R.sup.d is phenyl, 5- or 6-membered heteroaryl, or 3- to 6-membered heterocyclyl; wherein the substituent R.sup.d is unsubstituted or substituted by R.sup.e; R.sup.e is halogen, CN, NO.sub.2, C.sub.1-C.sub.6-haloalkyl, OH, C.sub.1-C.sub.6-alkoxy, C.sub.1-C.sub.6-haloalkoxy, C.sub.1-C.sub.6-alkylsulfonyl; R.sup.3 is halogen, CN, NO.sub.2, C.sub.1-C.sub.6-alkoxy or C.sub.3-C.sub.6-cycloalkyl; R.sup.4 is H, halogen, CN, C.sub.1-C.sub.6-haloalkyl or C.sub.1-C.sub.6-alkoxy; R.sup.5 is H, halogen, CN, C.sub.1-C.sub.6-haloalkyl or C.sub.1-C.sub.6-alkoxy; R.sup.6 is H, halogen, C.sub.1-C.sub.6-alkyl or C.sub.1-C.sub.6-haloalkyl; R.sup.7 is H, halogen, CN, C.sub.1-C.sub.6-alkyl or C.sub.1-C.sub.6-alkoxy.
14. The method of claim 12, wherein the variables R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6 and R.sup.7 are as defined in claim 12, R.sup.1 is C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkyl, HO—C.sub.1-C.sub.6-alkyl, C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-haloalkenyl, C.sub.2-C.sub.6-alkynyl, C.sub.3-C.sub.6-haloalkynyl, C.sub.1-C.sub.6-alkoxy-C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-alkoxy, C.sub.3-C.sub.6-alkenyloxy, C.sub.3-C.sub.6-haloalkenyloxy, C.sub.3-C.sub.6-alkynyloxy, C.sub.3-C.sub.6-haloalkynyloxy, C.sub.1-C.sub.6-haloalkoxy, C.sub.3-C.sub.6-cycloalkoxy, C.sub.3-C.sub.6-halocycloalkoxy, C.sub.3-C.sub.6-cycloalkenyloxy, C.sub.3-C.sub.6-halocycloalkenyloxy, C.sub.1-C.sub.6-alkylthio, C.sub.1-C.sub.6-haloalkylthio, (C.sub.1-C.sub.6-alkyl)amino, di(C.sub.1-C.sub.6-alkyl)amino, C.sub.1-C.sub.6-alkylsulfinyl, C.sub.1-C.sub.6-alkylsulfonyl, C.sub.3-C.sub.6-cycloalkyl, C.sub.3-C.sub.6-cycloalkenyl, C.sub.3-C.sub.6-halocycloalkyl, C.sub.3-C.sub.6-halocycloalkenyl, [1-(C.sub.1-C.sub.6-alkyl)]-C.sub.3-C.sub.6-cycloalkyl, [1-(C.sub.2-C.sub.6-alkenyl)]-C.sub.3-C.sub.6-cycloalkyl, [1-(C.sub.2-C.sub.6-alkynyl)]-C.sub.3-C.sub.6-cycloalkyl, [1-(C.sub.1-C.sub.6-haloalkyl)]-C.sub.3-C.sub.6-cycloalkyl, [1-(C.sub.2-C.sub.6-haloalkenyl)]-C.sub.3-C.sub.6-cycloalkyl, [1-(C.sub.3-C.sub.6-haloalkynyl)]-C.sub.3-C.sub.6-cycloalkyl, C.sub.3-C.sub.6-cycloalkyl-C.sub.1-C.sub.6-alkyl, C.sub.3-C.sub.6-cycloalkyl-C.sub.1-C.sub.6-haloalkyl, C.sub.3-C.sub.6-cycloalkyl-C.sub.1-C.sub.6-alkoxy, C.sub.3-C.sub.6-cycloalkyl-C.sub.1-C.sub.6-haloalkoxy, or 3- to 6-membered heterocyclyl; wherein the cyclic groups of R.sup.1 are unsubstituted or substituted by R.sup.a; R.sup.a is halogen, CN, NO.sub.2, C.sub.1-C.sub.6-alkoxy, or C.sub.1-C.sub.6-haloalkoxy; including agriculturally acceptable salts, amides, esters, or thioester of the pyrimidine compound of formula (I); with the exception of 5-(2-bromophenyl)-2-cyclopropyl-4-methyl-pyrimidine; 5-(2-bromophenyl)-2-ethyl-4- methyl-pyrimidine; and 5-(2-bromophenyl)-2-methoxy-4- methyl-pyrimidine.
15. The method of claim 12, wherein R.sup.1 is C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-alkoxy, C.sub.1-C.sub.6-haloalkoxy, C.sub.3-C.sub.6-alkenyloxy, C.sub.3-C.sub.6-haloalkenyloxy, C.sub.3-C.sub.6-alkynyloxy, C.sub.4-C.sub.6-haloalkynyloxy, C.sub.1-C.sub.6-alkylthio, or C.sub.3-C.sub.6-cycloalkyl wherein cycloalkyl is unsubstituted.
16. The method of claim 12, wherein R.sup.2 C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-haloalkenyl, C.sub.1-C.sub.6-alkoxy-C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-alkynyl, C.sub.3-C.sub.6-cycloalkenyl, C.sub.3-C.sub.6-cycloalkenyl-C.sub.1-C.sub.6-alkyl, C.sub.3-C.sub.6-cycloalkyl-C.sub.1-C.sub.6-alkylidenyl, C.sub.3-C.sub.6-halocycloalkyl-C.sub.1-C.sub.6-alkylidenyl, C.sub.3-C.sub.6-cycloalkenyl-C.sub.1-C.sub.6-alkylidenyl, C.sub.3-C.sub.6-hydroxycycloalkyl-C.sub.1-C.sub.6-alkyl, C.sub.3-C.sub.6-hydroxycycloalkenyl-C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-hydroxyalkyl, C.sub.3-C.sub.6-cycloalkyl-C.sub.2-C.sub.6-hydroxyalkylidenyl, hydroxycarbonyl-C.sub.1-C.sub.6-alkyl, hydroxycarbonyl-C.sub.1-C.sub.6-haloalkyl, C.sub.1-C.sub.6-alkoxycarbonyl-C.sub.1-C.sub.6-alkyl, C.sub.3-C.sub.6-hydroxycycloalkyl-C.sub.1-C.sub.6-hydroxyalkyl, C.sub.2-C.sub.6-dihydroxyalkyl, C.sub.3-C.sub.6-cycloalkyl-C.sub.3-C.sub.6-dihydroxyalkylidenyl, hydroxycarbonyl-C.sub.2-C.sub.6-dihydroxyalkyl, C.sub.1-C.sub.6-alkoxycarbonyl-C.sub.2-C.sub.6-dihydroxyalkyl, C.sub.1-C.sub.6-dicyanoalkyl, 5- or 6-membered heteroaryl, or (C.sub.1-C.sub.6-alkyl)carbonylaminocarbonyl; wherein OH groups of R.sup.2 are unsubstituted or substituted by R.sup.b, cyclic groups of R.sup.2 are unsubstituted or substituted by R.sup.c, and acyclic aliphatic groups of R.sup.2 are unsubstituted or substituted by R.sup.d; R.sup.b is C.sub.1-C.sub.6-alkyl, C.sub.3-C.sub.6-alkenyl, C.sub.3-C.sub.6-haloalkenyl, C.sub.3-C.sub.6-alkynyl, C.sub.3-C.sub.6-haloalkynyl, C.sub.3-C.sub.6-cycloalkyl, C.sub.3-C.sub.6-halocycloalkyl, C.sub.4-C.sub.6-cycloalkenyl, C.sub.3-C.sub.6-halocycloalkenyl, C.sub.1-C.sub.6-alkoxycarbonyl-C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkoxycarbonyl-C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-alkoxycarbonyl-C.sub.1-C.sub.6-haloalkyl, C.sub.1-C.sub.6-haloalkoxycarbonyl-C.sub.1-C.sub.6-haloalkyl, C.sub.1-C.sub.6-alkylcarbonyl, C.sub.1-C.sub.6-haloalkylcarbonyl, hydroxycarbonyl-C.sub.1-C.sub.6-alkyl, hydroxycarbonyl-C.sub.1-C.sub.6-haloalkyl, C.sub.1-C.sub.6-alkyloxycarbonyl, C.sub.1-C.sub.6-haloalkyloxycarbonyl, C.sub.1-C.sub.6-alkylthiocarbonyl, C.sub.1-C.sub.6-haloalkylthiocarbonyl, C.sub.1-C.sub.6-alkylaminocarbonyl, C.sub.1-C.sub.6-haloalkylaminocarbonyl, C.sub.1-C.sub.6-dialkylaminocarbonyl, C.sub.1-C.sub.6-dihaloalkylaminocarbonyl, C.sub.1-C.sub.6-alkylsulfonyl, C.sub.1-C.sub.6-haloalkylsulfonyl, C.sub.1-C.sub.6-haloalkoxy-C.sub.1-C.sub.6-haloalkyl, phenyl-C.sub.1-C.sub.6-alkyl, or phenyl-C.sub.1-C.sub.6-haloalkyl; R.sup.c is halogen, CN, NO.sub.2, C.sub.1-C.sub.6-haloalkyl, OH, C.sub.1-C.sub.6-alkoxy, C.sub.1-C.sub.6-haloalkoxy, C.sub.1-C.sub.6-alkylsulfinyl, or C.sub.1-C.sub.6-alkylsulfonyl; R.sup.d is phenyl, 5- or 6-membered heteroaryl, or 3- to 6-membered heterocyclyl; wherein the substituent R.sup.d is unsubstituted or substituted by R.sup.e; R.sup.e is halogen, CN, NO.sub.2, C.sub.1-C.sub.6-haloalkyl, OH, C.sub.1-C.sub.6-alkoxy, C.sub.1-C.sub.6-haloalkoxy, C.sub.1-C.sub.6-alkylsulfonyl.
17. The method of claim 12, wherein R.sup.3 is halogen, CN, NO.sub.2, C.sub.1-C.sub.6-alkoxy, or C.sub.3-C.sub.6-cycloalkyl; R.sup.4 is H, halogen, CN, C.sub.1-C.sub.6-haloalkyl, or C.sub.1-C.sub.6-alkoxy; R.sup.5 is H, halogen, CN, C.sub.1-C.sub.6-haloalkyl, or C.sub.1-C.sub.6-alkoxy; R.sup.6 is H, halogen, C.sub.1-C.sub.6-alkyl, or C.sub.1-C.sub.6-haloalkyl; R.sup.7 is H, halogen, CN, C.sub.1-C.sub.6-alkyl, or C.sub.1-C.sub.6-alkoxy.
18. The method of claim 12, wherein R.sup.1 is c-C.sub.3H.sub.5; R.sup.2 is C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-haloalkenyl, C.sub.1-C.sub.6-alkoxy-C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-alkynyl, C.sub.3-C.sub.6-cycloalkenyl, C.sub.3-C.sub.6-cycloalkenyl-C.sub.1-C.sub.6-alkyl, C.sub.3-C.sub.6-cycloalkyl-C.sub.1-C.sub.6-alkylidenyl, C.sub.3-C.sub.6-halocycloalkyl-C.sub.1-C.sub.6-alkylidenyl, C.sub.3-C.sub.6-cycloalkenyl-C.sub.1-C.sub.6-alkylidenyl, C.sub.3-C.sub.6-hydroxycycloalkyl-C.sub.1-C.sub.6-alkyl, C.sub.3-C.sub.6-hydroxycycloalkenyl-C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-hydroxyalkyl, C.sub.3-C.sub.6-cycloalkyl-C.sub.2-C.sub.6-hydroxyalkylidenyl, hydroxycarbonyl-C.sub.1-C.sub.6-alkyl, hydroxycarbonyl-C.sub.1-C.sub.6-haloalkyl, C.sub.1-C.sub.6-alkoxycarbonyl-C.sub.1-C.sub.6-alkyl, C.sub.3-C.sub.6-hydroxycycloalkyl-C.sub.1-C.sub.6-hydroxyalkyl, C.sub.2-C.sub.6-dihydroxyalkyl, C.sub.3-C.sub.6-cycloalkyl-C.sub.3-C.sub.6-dihydroxyalkylidenyl, hydroxycarbonyl-C.sub.2-C.sub.6-dihydroxyalkyl, C.sub.1-C.sub.6-alkoxycarbonyl-C.sub.2-C.sub.6-dihydroxyalkyl, C.sub.1-C.sub.6-dicyanoalkyl, 5- or 6-membered heteroaryl, or (C.sub.1-C.sub.6-alkyl)carbonylaminocarbonyl; wherein OH groups of R.sup.2 are unsubstituted or substituted by R.sup.b, cyclic groups of R.sup.2 are unsubstituted or substituted by R.sup.c, and acyclic aliphatic groups of R.sup.2 are unsubstituted or substituted by R.sup.d; R.sup.b is C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkyl, C.sub.3-C.sub.6-alkenyl, C.sub.3-C.sub.6-haloalkenyl, C.sub.3-C.sub.6-alkynyl, C.sub.3-C.sub.6-haloalkynyl, C.sub.3-C.sub.6-cycloalkyl, C.sub.3-C.sub.6-halocycloalkyl, C.sub.4-C.sub.6-cycloalkenyl, C.sub.3-C.sub.6-halocycloalkenyl, C.sub.1-C.sub.6-alkoxycarbonyl-C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkoxycarbonyl-C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-alkoxycarbonyl-C.sub.1-C.sub.6-haloalkyl, C.sub.1-C.sub.6-haloalkoxycarbonyl-C.sub.1-C.sub.6-haloalkyl, C.sub.1-C.sub.6-alkylcarbonyl, C.sub.1-C.sub.6-haloalkylcarbonyl, hydroxycarbonyl-C.sub.1-C.sub.6-alkyl, hydroxycarbonyl-C.sub.1-C.sub.6-haloalkyl, C.sub.1-C.sub.6-alkyloxycarbonyl, C.sub.1-C.sub.6-haloalkyloxycarbonyl, C.sub.1-C.sub.6-alkylthiocarbonyl, C.sub.1-C.sub.6-haloalkylthiocarbonyl, C.sub.1-C.sub.6-alkylaminocarbonyl, C.sub.1-C.sub.6-haloalkylaminocarbonyl, C.sub.1-C.sub.6-dialkylaminocarbonyl, C.sub.1-C.sub.6-dihaloalkylaminocarbonyl, C.sub.1-C.sub.6-alkylsulfonyl, C.sub.1-C.sub.6-haloalkylsulfonyl, C.sub.1-C.sub.6-alkoxy-C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkoxy-C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-alkoxy-C.sub.1-C.sub.6-haloalkyl, C.sub.1-C.sub.6-haloalkoxy-C.sub.1-C.sub.6-haloalkyl, phenyl-C.sub.1-C.sub.6-alkyl, or phenyl-C.sub.1-C.sub.6-haloalkyl; R.sup.c is halogen, CN, NO.sub.2, C.sub.1-C.sub.6-haloalkyl, OH, C.sub.1-C.sub.6-alkoxy, C.sub.1-C.sub.6-haloalkoxy, C.sub.1-C.sub.6-alkylsulfinyl, or C.sub.1-C.sub.6-alkylsulfonyl; R.sup.d is phenyl, 5- or 6-membered heteroaryl, or 3- to 6-membered heterocyclyl; wherein the substituent R.sup.d is unsubstituted or substituted by R.sup.e; R.sup.e is halogen, CN, NO.sub.2, C.sub.1-C.sub.6-haloalkyl, OH, C.sub.1-C.sub.6-alkoxy, C.sub.1-C.sub.6-haloalkoxy, C.sub.1-C.sub.6-alkylsulfonyl; R.sup.3 is Cl, Br, I, CH.sub.3, CF.sub.3, or CF.sub.2H; R.sup.4 is H; R.sup.5 is H or F; R.sup.6 is H, F, CF.sub.3, Cl, or Br; R.sup.7 is H or F.
19. The method of claim 12, wherein the compound of formula (I) corresponds to formula I.K, ##STR00332## wherein X and Y independently are selected from H, CHs, C.sub.2H.sub.5, n-propyl, iso-propyl, iso-butyl, n-butyl, 2-butyl, t-butyl, OH, OCH.sub.3, SCH.sub.3, S(O)CH.sub.3, S(O).sub.2CH.sub.3, CN, F, C.sub.1, Br, I, CH.sub.2CF.sub.3, CF.sub.2CF.sub.3, CF.sub.2CH.sub.3, CF.sub.3, CF.sub.2H, OCF.sub.2H, and OCF.sub.3; R.sup.1 is c-C.sub.3H.sub.5; R.sup.3 is Cl, Br, I, CHs, CF.sub.3, or CF.sub.2H; R.sup.5 is H or F; R.sup.6 is H, F, CF.sub.3, Cl, or Br; R.sup.7 is H or F.
20. A method of controlling undesired vegetation, which comprises allowing a herbicidal active amount of the composition of claim 10 to act on plants, their environment or on seed.
21. A method of controlling undesired vegetation, which comprises allowing a herbicidal active amount of the composition of claim 11 to act on plants, their environment or on seed.
Description
A PREPARATION EXAMPLES
Example 1: 3-[5-(2-chlorophenyl)-2-cyclopropyl-pyrimidin-4-yl]-2-OH-propanoic acid
1.1 5-(2-chlorophenyl)-2-cyclopropyl-4-CH.SUB.3.-pyrimidine
(1) A solution of 1-(2-Chlorophenyl)-2-propanone (31 g) in dimethylformamiddimethylacetal (60 mL) was stirred for 2 h at 125° C. TLC showed that the SM was consumed (PE:EtOAc=1:1). The mixture was concentrated to give (E)-3-(2-chlorophenyl)-4-(dimethylamino)but-3-en-2-one (41 g, 99.5%) as a yellow oil and used directly without purification. To a solution of the crude (E)-3-(2-chlorophenyl)-4-(dimethylamino)but-3-en-2-one (33.6 g) in EtOH (600 mL) was added cyclopropanecarboxamidine hydrochloride (45 g) and t-BuOK (42 g). The resulting mixture was stirred for 16 h at 90° C. TLC (PE:EtOAc=3:1) showed that the SM was consumed. The mixture was filtered, and the filtrate was concentrated, purified by column (gradient EtOAc: PE=from 0:1 to 1:10) to give 5-(2-chlorophenyl)-2-cyclopropyl-4-CH.sub.3-pyrimidine (29 g, 79.23%) as a yellow oil.
(2) .sup.1H NMR CDCl3 400 MHz: δ: 1.04-1.11 (m, 2H); 1.16-1.23 (m, 2H); 2.19-2.36 (m, 1H); 2.3 (s, 3H); 7.17-7.23 (m, 1H) 7.30-7.41 (m, 2H) 7.43-7.56 (m, 1H) 8.28 (s, 1H).
1.2 ethyl 3-[5-(2-chlorophenyl)-2-cyclopropyl-pyrimidin-4-yl]-2-OH-propanoate
(3) To a solution of 5-(2-chlorophenyl)-2-cyclopropyl-4-CH.sub.3-pyrimidine (3 g) in THF (60 mL) was added LDA (8 mL) dropwise at −78° C. 10 min later, glyoxalic acid ethylester (1.6 g) in THF was added dropwise. The mixture was stirred at −78° C. for 1 h. aq. NH.sub.4Cl (60 mL) was added. The mixture was extracted with EtOAc, dried over Na.sub.2SO.sub.4 and concentrated. The crude was purified by column (PE:EtOAc=50:1 to 2:1) to give ethyl 3-[5-(2-chlorophenyl)-2-cyclopropyl-pyrimidin-4-yl]-2-OH-propanoate (3 g, 47.2%) as a yellow oil.
(4) .sup.1H NMR: CDCl.sub.3 400 MHz δ ppm 1.11-1.19 (m, 4H); 1.23 (m, 3H); 2.19-2.34 (m, 1H); 2.89-3.06 (m, 1H); 3.08-3.17 (m, 1H); 4.10-4.27 (m, 3H); 4.32-4.41 (m, 1H); 4.46-4.55 (m, 1H); 4.58-4.70 (m, 1H); 7.20-7.26 (m, 1H); 7.33-7.42 (m, 2H); 7.51 (d, 1H); 8.35 (s, 1H).
1.3 3-[5-(2-chlorophenyl)-2-cyclopropyl-pyrimidin-4-yl]-2-OH-propanoic acid
(5) A solution of ethyl 3-[5-(2-chlorophenyl)-2-cyclopropyl-pyrimidin-4-yl]-2-OH-propanoate (1 g) in MeOH (30 ml) and THF (30 mL) and H.sub.2O (10 mL) was cooled to 0° C. Then LiOH.H.sub.2O (0.36 g) in H.sub.2O was added. The mixture was stirred at 20° C. for 15 h. The mixture was concentrated. The residue was adjusted to pH=2-3 with 1N HCl, and extracted with EtOAc. The organic layer was dried over Na.sub.2SO.sub.4 and concentrated. The crude product was purified by prep-HPLC to give 3-[5-(2-chlorophenyl)-2-cyclopropyl-pyrimidin-4-yl]-2-OH-propanoic acid (0.6 g, 66.7%) as a yellow oil.
(6) .sup.1H NMR: CDCl.sub.3 400 MHz δ ppm 1.36 (m, 4H); 2.44 (m, 1H); 3.06-3.38 (m, 2H); 4.55 (m, 1H); 7.29 (m, 1H); 7.39-7.51 (m, 2H); 7.53-7.60 (m, 1H); 8.60 (s, 1H); 9.06 (br. s., 1H).
Example 2 1-[5-(2-chlorophenyl)-2-cyclopropyl-pyrimidin-4-yl]-2-CH.SUB.3.-propane-1,2-diol
2.11-[5-(2-chlorophenyl)-2-cyclopropyl-pyrimidin-4-yl]-2-CH.SUB.3.-propan-2-ol
(7) To a solution of 5-(2-chlorophenyl)-2-cyclopropyl-4-CH.sub.3-pyrimidine (1.3 g) in THF (30 mL) was added 2M LDA solution in THF (3.5 mL) dropwise at −78° C. 10 min later, CH.sub.3COCH.sub.3 (0.4 g) in THF was added dropwise. Then the mixture was stirred at −78° C. for 1 h. aq. NH.sub.4Cl (30 mL) was added. The mixture was extracted with EtOAc, dried over Na.sub.2SO.sub.4 and concentrated. The crude product was purified by column chromatography (PE:EtOAc=50:1 to 5:1) to give 1-[5-(2-chlorophenyl)-2-cyclopropyl-pyrimidin-4-yl]-2-CH.sub.3-propan-2-ol (1.1 g, 68.8%) as a yellow oil.
(8) .sup.1H NMR: CDCl.sub.3 400 MHz δ ppm 1.09 (s, 3H); 1.14-1.22 (m, 5H); 2.24-2.38 (m, 1H); 2.54-2.66 (m, 1H); 2.69-2.79 (m, 1H); 6.08 (s, 1H); 7.18 (m, 1H); 7.32-7.45 (m, 2H); 7.52 (m, 1H); 8.37 (s, 1H).
2.2 5-(2-chlorophenyl)-2-cyclopropyl-4-(2-CH.SUB.3.-prop-1-enyl)pyrimidine
(9) To a solution of 1-[5-(2-chlorophenyl)-2-cyclopropyl-pyrimidin-4-yl]-2-CH.sub.3-propan-2-ol (1.1 g) in toluene (30 mL) was added PPTS (0.18 g). The mixture was stirred at 100° C. for 10 h. Brine (30 mL) was added. Then the mixture was extracted with EtOAc, dried over Na.sub.2SO.sub.4 and concentrated. The crude was purified by column (PE:EtOAc=50:1 to 30:1) to give 5-(2-chlorophenyl)-2-cyclopropyl-4-(2-CH.sub.3-prop-1-enyl)pyrimidine (0.8 g, 81.6%) as a yellow oil.
2.3 1-[5-(2-chlorophenyl)-2-cyclopropyl-pyrimidin-4-yl]-2-CH.SUB.3.-propane-1,2-diol
(10) To a solution of 5-(2-chlorophenyl)-2-cyclopropyl-4-(2-CH.sub.3-prop-1-enyl)pyrimidine (0.45 g) in THF (10 mL) was added NMO (0.35 g) and K.sub.2OsO.sub.4.2H.sub.2O (0.049 g). Then the mixture was stirred at 30° C. for 12 h. The mixture was concentrated in vacuum. The crude product was purified by column chromatography (PE:EtOAc=50:1 to 5:1) to give -[5-(2-chlorophenyl)-2-cyclopropyl-pyrimidin-4-yl]-2-CH.sub.3-propane-1,2-diol (0.2 g, 41.9%) as a yellow oil.
(11) .sup.1H NMR: CDCl.sub.3 400 MHz δ ppm (2 rotamers) 0.95-1.33 (m, 2×10 H); 2.38-2.55 (m, 2×1 H); 4.33 (s, 1H); 4.35 (s, 1H); 5.86 (br, 2×2 H); 7.23 (m, 2×1 H); 7.39-7.47 (m, 2×2 H); 7.54 7.58 (m, 2×1 H); 8.52-8.66 (s, 1H); 8.68-8.69 (s, 1H).
Example 3 methyl 2-[5-(2-chlorophenyl)-2-cyclopropyl-pyrimidin-4-yl]-2-OH-propanoate
3.1 5-(2-chlorophenyl)-2-cyclopropyl-pyrimidine
(12) To a solution of 5-bromo-2-cyclopropyl-pyrimidine (5.3 g) in dry dioxane (40 ml) was added 2-chloro-phenylboronic acid (8.5 g), K.sub.2CO.sub.3 (7.4 g) and Pd(dppf)Cl.sub.2.xCH.sub.2Cl.sub.2 (550 mg) under N.sub.2. The resulting mixture was heated at 100° C. overnight. Then the mixture was diluted with water, extracted with EtOAc. The combined organic layers were washed with brine, dried over anhydrous Na.sub.2SO.sub.4, filtered and concentrated to give crude product (8 g), which was purified by column (PE:EtOAc=5:1) to afford 5-(2-chlorophenyl)-2-cyclopropyl-pyrimidine (4 g, 60%).
(13) .sup.1H NMR: CDCl.sub.3 400 MHz δ 8.69 (s, 2H), 7.2-7.6 (m, 4H), 2.35 (br s, 1H), 1.05-1.30 (m, 4H).
3.2 methyl 2-[5-(2-chlorophenyl)-2-cyclopropyl-pyrimidin-4-yl]-2-OH-propanoate
(14) To a solution of 2,2,6,6-tetramethylpiperidine (1.6 g) in dry THF (50 mL) was added dropwise n-BuLi (10.8 mL) at −78° C. under N.sub.2. The resulting mixture was stirred at −78° C. for 1 h. Then 5-(2-chlorophenyl)-2-cyclopropyl-pyrimidine (1 g) in 10 mL THF was added dropwised at −78° C. After stirred for 5 min, methlypyruvate (2.2 g) was added. The mixture was stirred while warming from −78° C. to room temperature. Then aq. NH.sub.4Cl was added at 0° C. The mixture was extracted with EtOAc. The combined organic layers were washed with saturated brine, dried over anhydrous Na.sub.2SO.sub.4, filtered, concentrated and purified by column chromatography (PE:EtOAc=10:1) to give methyl 2-[5-(2-chlorophenyl)-2-cyclopropyl-pyrimidin-4-yl]-2-OH-propanoate (200 mg, 14%) as a white solid.
(15) .sup.1H NMR: MeOD 400 MHz (2 rotamers) δ 8.35 (s, 1H), 8.29 (s, 1H), 7.2-7.5 (m, 2×4 H), 3.66 3.73 (2s, 2×3H), 2.18-2.38 (m, 2×1 H), 1.63 (s, 3H), 1.53 (s, 3H), 1.06-1.25 (m, 2×4 H).
Example 4: 5-(2-chlorophenyl)-2-cyclopropyl-4-(3-CH.SUB.3.-2-furyl)pyrimidine
4.1 a 2-(2-chlorophenyl)-1-(3-CH.SUB.3.-2-furyl)ethanone
(16) To a solution of N-methoxy-N,3-dimethyl-furan-2-carboxamide (1.5 g) in dry THF (60 mL) under Argon is added at −78° C. chloro-[(2-chlorophenyl)-CH.sub.3]magnesium (CAS 29874-00-8) drop wise. The reaction mixture is stirred for 1 h at −78° C. warmed to room temperature and stirred for 16 h. The reaction was quenched with brine (60 mL), extracted with ethyl acetate, dried and concentrated. The product was purified by column chromatography (gradient cyclohexane/ethyl acetate=from 1:0 to 3:2) to give 2-(2-chlorophenyl)-1-(3-CH.sub.3-2-furyl)ethanone (1.05 g, 50.5%).
(17) .sup.1H NMR CDCl3 400 MHz: δ 7.46-7.36 (m, 2H), 7.30-7.19 (m, 3H), 6.41 (d, J=1.7 Hz, 1H), 4.33 (s, 2H), 2.39 (s, 3H).
4.1 b 2-(2-chlorophenyl)-1-(3-CH.SUB.3.-2-furyl)ethanone
(18) To a suspension of NaH (60%, 1.61 g) in dry DMF (60 mL) under Argon is added at −10° C. 2-(3-CH.sub.3-2-furyl)-2-morpholino-acetonitrile (7.6 g). The reaction is stirred for 30 min. followed by addition of a solution of 1-(bromomethyl)-2-chloro-benzene (6.88 g) in dry DMF. The reaction is warmed to room temperature and stirred for 16 h. The mixture is poured into a saturated aq. ammonium chloride solution, extracted with ethyl acetate, washed with water and aq. LiCl solution (10%), dried and concentrated. The residue is dissolved in a mixture of methanol and water (7:3) and CuSO.sub.4 (16.7 g) is added. The reaction mixture is stirred for 1.5 h at 60° C. After concentration of the mixture, water is added, the mixture is extracted with ethyl acetate, washed with saturated aq. sodium sulfite solution and brine, dried and concentrated. The product is purified by column chromatography (gradient cyclohexane/ethyl acetate=from 1:0 to 3:2) to give 2-(2-chlorophenyl)-1-(3-CH.sub.3-2-furyl)ethanone (5.0 g, 63.6%).
(19) .sup.1H NMR CDCl3 400 MHz: δ 7.46-7.36 (m, 2H), 7.30-7.19 (m, 3H), 6.41 (d, J=1.7 Hz, 1H), 4.33 (s, 2H), 2.39 (s, 3H).
4.2 2-(2-chlorophenyl)-3-(dimethylamino)-1-(3-CH.SUB.3.-2-furyl)prop-2-en-1-one
(20) A solution of 2-(2-chlorophenyl)-1-(3-CH.sub.3-2-furyl)ethanone (1.05 g) in dimethylformamidedimethylacetal (6 mL) was stirred for 16 h at 65° C. TLC showed that the SM was consumed. The mixture was concentrated and purified by column chromatography (gradient cyclohexane/ethyl acetate=from 1:0 to 1:9) to give 2-(2-chlorophenyl)-3-(dimethylamino)-1-(3-CH.sub.3-2-furyl)prop-2-en-1-one (700 mg, 54.0%).
(21) .sup.1H NMR CDCl3 400 MHz: δ 7.68 (s, 1H), 7.42-7.34 (m, 1H), 7.29-7.16 (m, 3H), 7.13 (d, J=1.7 Hz, 1H), 6.25 (d, J=1.7 Hz, 1H), 2.78 (s, 6H), 2.32 (s, 3H).
4.3 5-(2-chlorophenyl)-2-cyclopropyl-4-(3-C H.SUB.3.-2-furyl)pyrimidine
(22) To a solution of 2-(2-chlorophenyl)-3-(dimethylamino)-1-(3-CH.sub.3-2-furyl)prop-2-en-1-one (4.9 g) in EtOH (100 mL) was added cyclopropanecarboxamidine hydrochloride (2.24 g) and NaOEt (21%, 6.93 g). The resulting mixture was stirred for 16 h at reflux. TLC (PE:EtOAc=3:1) showed that the SM was consumed. The mixture was filtered, and the filtrate was concentrated, purified by column (gradient EtOAc: PE=from 0:1 to 1:0) to give 5-(2-chlorophenyl)-2-cyclopropyl-4-CH.sub.3-pyrimidine (4.0 g, 73%) as a yellow solid.
(23) .sup.1H NMR CDCl3 400 MHz: δ 8.38 (s, 1H), 7.52-7.36 (m, 1H), 7.37-7.17 (m, 3H), 7.05 (d, J=1.7 Hz, 1H), 6.27 (d, J=1.7 Hz, 1H), 2.43 (s, 3H), 2.37-2.28 (m, 1H), 1.27-1.21 (m, 2H), 1.14-1.08 (m, 2H).
Example 5: N-acetyl-5-(2-chlorophenyl)-2-cyclopropyl-pyrimidine-4-carboxamide
5.1 5-Bromo-2-cyclopropyl-pyrimidine-4-carboxylic acid
(24) NaH (60% purity, 41.9 g) is added in portions to EtOH (800 mL) at 0° C. The resulting mixture is warmed to ambient temperature and the cyclopropanecarboxamidine hydrochlorid (93.5 g) is added in portions. The reaction is warmed to 50° C. and maintained at this temperature for 0.5 h and then cooled to ambient temperature before mucobromic acid (100 g) is added in EtOH while keeping the internal temperature below 55° C. The mixture is allowed to cool to ambient temperature and stirred for additional 16 h. All solid components are removed by filtration and the resulting solution is concentrated under reduced pressure. Aq. HCl (1 mol/L) is added, the aqueous phase is washed with EtOAc (3×), the combined organic extracts are dried over MgSO4 and the solid parts removed by filtration. The residue is concentrated under reduced pressure and the resulting solid titrated with (iPr).sub.2O. The solids are collected by filtration and dried yielding the title compound (68.0 g, yield 72%) as a colorless solid.
(25) 1H NMR (400 MHz, CDCl.sub.3): δ=8.91 (s, 1H), 2.38-2.26 (m, 1H), 1.34-1.14 (m, 4H) ppm; MS (ESI) m/z 244.9 [M+H+].
5.2 Methyl 5-bromo-2-cyclopropyl-pyrimidine-4-carboxylate
(26) 5-Bromo-2-cyclopropyl-pyrimidine-4-carboxylic acid (91.0 g) is dissolved in MeOH (1200 mL) and conc. sulfuric acid (20 mL) is added dropwise at ambient temperature. The reaction is heated to reflux and stirred for 16 h. The resulting mixture is cooled to ambient temperature and neutralized with aq. sat. NaHCO.sub.3. The residue is parted between EtOAc and aq. sat. NaHCO.sub.3, the phases are separated, the aq. phase is extracted with EtOAc and the combined organics are dried over MgSO.sub.4. Solid parts are removed by filtration and the organic phase is concentrated under reduced pressure. Column chromatography of the resulting crude product (ISCO-CombiFlash Rf, cyclohexane/EtOAc) yields the title compound (1.48 g, yield 63%) as a colorless solid.
(27) .sup.1H NMR (400 MHz, CDCl.sub.3): δ=8.74 (s, 1H), 4.01 (s, 3H), 2.33-2.22 (m, 1H), 1.21-1.06 (m, 4H) ppm; MS (ESI) m/z 246.9 [M+H+].
5.3 methyl 5-(2-chlorophenyl)-2-cyclopropyl-pyrimidine-4-carboxylate
(28) A mixture of methyl 5-bromo-2-cyclopropyl-pyrimidine-4-carboxylate (8.00 g), 2-(chlorophenyl)boronic acid (5.11 g), K.sub.3PO.sub.4 (8.89 g) and PdCl.sub.2dppf (4.19 g) in dioxane (120 mL) and water is heated under reflux under an atmosphere of argon for 5 h. Water and EtOAc are added, the phases are separated and organic phase is dried over MgSO.sub.4. The solids are removed via filtration and resulting solution is concentrated under reduced pressure. Column chromatography of the crude product (ISCO-CombiFlash Rf) yields the title compound (3.00 g, yield 48%).
(29) .sup.1H NMR (400 MHz, CDCl.sub.3): δ 8.60 (s, 1H), 7.52-7.44 (m, 1H), 7.49-7.47 (m, 1H), 7.39-7.34 (m, 2H), 7.26-7.24 (m, 1H), 3.79 (s, 3H), 2.45-2.39 (m, 1H), 1.28-1.24 (m, 2H), 1.19-1.14 (m, 2H) ppm; MS (ESI) m/z 289.1 [M+H+].
5.4 5-(2-chlorophenyl)-2-cyclopropyl-pyrimidine-4-carboxylic acid
(30) Methyl 5-(2-chlorophenyl)-2-cyclopropyl-pyrimidine-4-carboxylate (3.00 g) is dissolved in THF and lithiumhydroxid (373 mg) followed by water until the base is completely dissolved. The resulting mixture is stirred for 2 hours at ambient temperature; the volatiles are removed under reduced pressure and the remains are then acidified to pH=1-2 with aqueous hydrochloric acid. The aq. phase is extracted with EtOAc and the combined organics are dried over MgSO.sub.4. Solid parts are removed by filtration and the organic phase is concentrated under reduced pressure yielding the title compound (2.00 g, yield 70%) as a colorless solid.
(31) .sup.1H NMR (400 MHz, CDCl.sub.3): δ 10.94 (brs, 1H), 8.67 (s, 1H), 7.51-7.49 (m, 1H), 7.42-7.35 (m, 1H), 7.24-7.22 (m, 1H), 2.45-2.39 (m, 1H), 1.29-1.22 (m, 4H) ppm; MS (ESI) m/z 275.0 [M+H+].
5.5: 5-(2-chlorophenyl)-2-cyclopropyl-pyrimidine-4-carboxamide
(32) To a solution of 5-(2-chlorophenyl)-2-cyclopropyl-pyrimidine-4-carboxylic acid (1.0 g) in DCM (15 mL) are added DMF (2 drops) and oxalyl chloride (924 mg) and the mixture is stirred for 16 h at room temperature. This mixture is added to a mixture of a 2 M solution of ammonia in dioxane (3.64 mL) and triethylamine (1.11 mL) in DCM (10 mL). The combined mixtures are stirred for 16 h at room temperature. After addition of water the mixture was stirred for 5 minutes and separated. The organic phase was concentrated and purified by column chromatography yielding 5-(2-chlorophenyl)-2-cyclopropyl-pyrimidine-4-carboxamide (696 mg 70%).
(33) .sup.1H NMR (400 MHz, Chloroform-d) δ 8.67 (s, 1H), 7.52-7.47 (m, 1H), 7.43-7.31 (m, 2H), 7.25-7.20 (m, 1H), 2.48-2.35 (m, 1H), 1.34-1.21 (m, 4H).
5.6: N-acetyl-5-(2-chlorophenyl)-2-cyclopropyl-pyrimidine-4-carboxamide
(34) To a solution of 5-(2-chlorophenyl)-2-cyclopropyl-pyrimidine-4-carboxamide (230 mg) in dry THF (10 mL) is added a 1M solution of LiHMDS in THF (0.84 mL) at −20° C. After stirring for 10 min. at −20° C. acetic anhydride (129 mg) is added and the reaction is warmed to room temperature and stirred for 16 h. Water is added, the aq. phase is extracted with ethyl acetate. The combined organic extracts are washed with water and brine, dried and concentrated. Purification by column chromatography (gradient EtOAc:CH=from 0:1 to 1:4) yielded N-acetyl-5-(2-chlorophenyl)-2-cyclopropyl-pyrimidine-4-carboxamide (30 mg, 11%).
(35) .sup.1H NMR (400 MHz, Chloroform-d) δ 10.25 (s, 1H), 8.60 (d, J=0.9 Hz, 1H), 7.56-7.45 (m, 1H), 7.45-7.34 (m, 2H), 7.33-7.18 (m, 1H), 2.48 (s, 3H), 2.44-2.36 (m, 1H), 1.32-1.19 (m, 6H).
Example 6: ethyl 2-[5-(2-chlorophenyl)-2-methoxy-pyrimidin-4-yl]acetate
(36) To a solution of 5-(2-chlorophenyl)-2-methoxy-4-CH.sub.3-pyrimidine (1.0 g) in dry THF (25 mL) is added a 1 M solution of LiHMDS (8.52 mL) at 0° C. and the mixture is stirred for 30 min. at 0° C. To this mixture is added diethylcarbonate (2.11 g) and the mixture is slowly warmed to room temperature and stirred for 22 h. Saturated aq. Ammonium chloride solution is added and the mixtures is extracted 3 times with ethyl acetate. The organic phase was concentrated and purified by column chromatography yielding ethyl 2-[5-(2-chlorophenyl)-2-methoxy-pyrimidin-4-yl]acetate (900 mg, 95% purity, 65% yield).
(37) .sup.1H NMR DMSO-d6 500 MHz: 8.48 (s, 1H), 7.65-7.60 (m, 1H), 7.53-7.43 (m, 2H), 7.42-7.37 (m, 1H), 4.01-3.90 (m, 5H), 3.71-3.50 (m, 2H), 1.07 (t, J=7.1 Hz, 3H).
Example 7: methyl 2-[5-(2-bromophenyl)-2-cyclopropyl-pyrimidin-4-yl]-2-CH.SUB.3.-propanoate
(38) To a solution of methyl 2-[5-(2-bromophenyl)-2-cyclopropyl-pyrimidin-4-yl]acetate (800 mg) in dry THF (30 mL) is added iodomethane (1.31 g) at −78° C., followed by addition of potassium tert-butanolate (776 mg). The mixture is stirred for 1 h at −78° C. The mixture is slowly warmed to room temperature and stirred for 65 h at room temperature. Reaction control shows conversion to mono- and di-methyl product. Another portion of Iodomethane (1.31 g) and potassium tert-butanolate (776 mg) is added and the mixture is stirred 16 h at room temperature. After addition of water, the mixture is extracted with ethyl acetate, washed with saturated aq. sodium bicarbonate solution, dried and concentrated. The product is purified by column chromatography to give methyl 2-[5-(2-bromophenyl)-2-cyclopropyl-pyrimidin-4-yl]-2-CH.sub.3-propanoate (210 mg, 24.3%).
(39) .sup.1H NMR (400 MHz, Chloroform-d) δ 8.22 (s, 1H), 7.68 (dd, J=7.9, 1.3 Hz, 1H), 7.34 (td, J=7.5, 1.3 Hz, 1H), 7.30-7.22 (m, 1H), 7.19 (dd, J=7.5, 1.8 Hz, 1H), 3.48 (s, 3H), 2.33-2.24 (m, 1H), 1.48 (s, 3H), 1.37 (s, 3H), 1.23-1.14 (m, 2H), 1.15-1.04 (m, 2H).
Example 7: [5-(2-Chlorophenyl)-2-cyclopropyl-pyrimidin-4-yl]methanol
(40) DIBAlH (1 N in THF, 38.8 mL) is added dropwise to a solution of methyl 5-(2-chlorophenyl)-2-cyclopropyl-pyrimidine-4-carboxylate (5.60 g) in THF (50 mL) at 0° C. Upon completion of the addition the reaction mixture is warmed to ambient temperature and stirred for 2 h. EtOAc (50 mL) is slowly added and the mixture is stirred for 15 min before aq. NaOH (2 mol/L) is added at 0° C. until the phases are clear. The phases are separated and the aq. phase is extracted with EtOAc (2×). The combined organics are dried over MgSO.sub.4, solid parts are removed by filtration and the organic phase is concentrated under reduced pressure yielding the title compound (4.00 g, yield 79%).
(41) .sup.1H NMR (400 MHz, CDCl.sub.3): δ 8.36 (s, 1H), 7.53-7.51 (m, 1H), 7.42-7.34 (m, 2H), 7.21-7.17 (m, 1H), 4.46 (d, J=22.0 Hz, 2H), 2.42-2.35 (m, 1H), 1.27-1.23 (m, 2H), 1.20-1.15 (m, 2H) ppm; MS (ESI) m/z 261.0 [M+H+].
Example 8: 2-[5-(2-chloro-4-fluorophenyl)-2-cyclopropyl-pyrimidin-4-yl]propan-2-ol
(42) MeMgBr (3N in Et.sub.2O, 2.18 mL) is added dropwise to a solution of methyl 5-(2-chlorophenyl)-2-cyclopropyl-pyrimidine-4-carboxylate (1.00 g) in Et.sub.2O (20 mL) at −20° C. Upon completion of the addition the reaction mixture is warmed to 0° C. and stirred for 1 h. EtOAc and aq. sat. NH.sub.4Cl is added and the phases are separated. The organic phase is dried over MgSO.sub.4, solid parts are removed by filtration and the organic phase is concentrated under reduced pressure. Purification by column chromatography (ISCO-CombiFlash Rf, reversed phase, MeCN/water)) yields the title compound (810 mg, 95%) as a colorless oil.
(43) .sup.1H NMR (400 MHz, DMSO-d.sub.6): δ 8.22 (s, 1H), 7.48 (dd, J=9.0, 2.6 Hz, 1H), 7.40 (dd, J=8.6, 6.3 Hz, 1H), 7.23 (td, J=8.6, 2.6 Hz, 1H), 4.84 (s, 1H), 2.33-2.17 (m, 1H), 1.37 (s, 3H), 1.35 (s, 3H), 1.13-0.98 (m, 4H) ppm; MS (ESI) m/z 307.0 [M+H+].
Example 9: 1-[5-(2-chlorophenyl)-2-cyclopropyl-pyrimidin-4-yl]ethanol
9.1: 5-(2-chlorophenyl)-2-cyclopropyl-pyrimidine-4-carbaldehyde
(44) A mixture of [5-(2-Chlorophenyl)-2-cyclopropyl-pyrimidin-4-yl]methanol (2.00 g) and MnO.sub.2 (8.00 g) in chloroform (20 mL) are heated under reflux for 16 h. Solid parts are removed by filtration and the organic phase is concentrated under reduced pressure. Purification by column chromatography (ISCO-CombiFlash Rf, cyclohexane/EtOAc) yields the title compound (1.50 g, 76%).
(45) .sup.1H NMR (400 MHz, CDCl.sub.3): δ 9.95 (s, 1H), 8.64 (s, 1H), 7.51-7.48 (m, 1H), 7.44-7.36 (m, 2H), 7.26-7.24 (m, 1H), 2.48-2.41 (m, 1H), (tt, J=8.1, 4.8 Hz, 1H), 1.31-1.26 (m, 2H), 1.23-1.17 (m, 2H) ppm; MS (ESI) m/z 259.0 [M+H+].
9.2: 1-[5-(2-chlorophenyl)-2-cyclopropyl-pyrimidin-4-yl]ethanol
(46) MeMgBr (3N in Et.sub.2O, 33.4 mL) is added dropwise to a solution of 5-(2-chlorophenyl)-2-cyclopropyl-pyrimidine-4-carbaldehyde (23.6 g) in Et.sub.2O (200 mL) at −10° C. Upon completion of the addition the reaction mixture is warmed to 25° C. and stirred for 1 h. EtOAc and aq. sat. NH.sub.4Cl are added and the phases are separated. The organic phase is dried over MgSO.sub.4, solid parts are removed by filtration and the organic phase is concentrated under reduced pressure. Purification by column chromatography (ISCO-CombiFlash Rf, reversed phase, MeCN/water)) yields the title compound (17.9 g, 68%) as a colorless oil.
(47) .sup.1H NMR (400 MHz, CDCl.sub.3, 2 rotamers): δ 8.37 (s, 1H), 8.31 (s, 1H), 7.55-7.50 (m, 2H), 7.42-7.33 (m, 4H), 7.25-7.16 (m, 2H), 4.79-4.69 (m, 1H), 4.36-4.33 (m, 1H), 2.38-2.32 (m, 2H), 1.25-1.22 (m, 4H), 1.18-1.12 (m, 10H) ppm; MS (ESI) m/z 275.0 [M+H+].
Example 10: 5-(2-chlorophenyl)-2-cyclopropyl-4-(1-methoxyethyl)pyrimidine
(48) NaH (21.2 mg) is added to a solution of 1-[5-(2-chlorophenyl)-2-cyclopropyl-pyrimidin-4-yl]ethanol (210 mg) in DMF (5 mL) at 0° C. The mixture is warmed to 25° C. and stirred for 30 min before MeI (52.6 μL) is added. The reaction is stirred for 2 h at 25° C. Water and EtOAc are and the phases are separated. The organic phase is dried over MgSO.sub.4, solid parts are removed by filtration and the organic phase is concentrated under reduced pressure. Purification by column chromatography (ISCO-CombiFlash Rf, reversed phase, MeCN/water)) yields the title compound (80.0 mg, 36%) as a colorless oil.
(49) .sup.1H NMR (400 MHz, CDCl.sub.3, 2 rotamers): δ 8.46 (s, 1H), 8.33 (s, 1H), 7.65-7.60 (m, 2H), 7.53-7.39 (m, 6H), 4.15-4.08 (m, 2H), 3.00 (s, 3H), 2.93 (s, 3H), 2.31-2.25 (m, 2H), 1.34 (d, J=XX Hz, 3H), 1.25 (d, J=6.4 Hz, 3H), 1.12-1.05 (m, 8H) ppm; MS (ESI) m/z 289.0 [M+H+].
(50) Below listed are the meaning of abbreviations used in preparation process above.
(51) CH cyclohexane
(52) EtOH ethanol
(53) DCM dichloromethane
(54) DMF dimethylformamide
(55) PE petrol ether
(56) TLC thin layer chromatography
(57) EtOAc ethylacetate
(58) SM starting material
(59) LDA lithium diisopropylamide
(60) LiHMDS lithium bis(trimethylsilyl)amide
(61) MeOH methanol
(62) NaHMDS sodium bis(trimethylsilyl)amide
(63) TH F tetrahydrofuran
(64) Prep-HPLC preparative high pressure liquid chromatography
(65) NMO N-methylmorpholine-N-oxide
(66) PPTS pyridinium p-tolouolsulfonate
(67) LAH Lithium aluminium hydride
(68) DIBAlH Diisobutylaluminium hydride
(69) PCC Pyridinium Chlorochromate.
(70) With appropriate modification of the starting materials, the procedures given in the synthesis examples below were used to obtain further compounds of formula I. The compounds obtained in this manner are listed in the Table X that follows, together with physical data.
(71) The products shown below were characterized by melting point determination, by the masses ([m/z]) or retention time (RT; [min.]) determined by HPLC-MS or HPLC spectrometry.
(72) HPLC-MS=high performance liquid chromatography-coupled mass spectrometry; HPLC methods:
(73) Method: Column: Phenomenex Kinetex 1.7 μm XB-C18 100A; 50×2.1 mm; mobile phase: A: water+0.1% trifluoroacetic acid (TFA); B: acetonitrile+0.1% TFA; gradient: 5-100% B in 1.50 minutes; 100% B 0.25 min; flow: 0.8-1.0 ml/min in 1.51 minutes at 60° C. MS: quadrupole electrospray ionization, 80 V (positive mode).
(74) ##STR00041##
(75) TABLE-US-00006 TABLE X HPLC/MS, HPLC/MS, Ex. R.sup.1 R.sup.2 R.sup.3 R.sup.4 R.sup.5 R.sup.6 R.sup.7 R.sub.t [min] m/z Ex. 1 c-C.sub.3H.sub.5
B USE EXAMPLES
(76) The herbicidal activity of the pyrimidine compounds of formula (I) was demonstrated by the following greenhouse experiments:
(77) The culture containers used were plastic flowerpots containing loamy sand with approximately 3.0% of humus as the substrate. The seeds of the test plants were sown separately for each species.
(78) For the pre-emergence treatment, the active ingredients, which had been suspended or emulsified in water, were applied directly after sowing by means of finely distributing nozzles. The containers were irrigated gently to promote germination and growth and subsequently covered with transparent plastic hoods until the plants had rooted. This cover caused uniform germination of the test plants, unless this had been impaired by the active ingredients.
(79) For the post-emergence treatment, the test plants were first grown to a height of 3 to 15 cm, depending on the plant habit, and only then treated with the active ingredients which had been suspended or emulsified in water. For this purpose, the test plants were either sown directly and grown in the same containers, or they were first grown separately as seedlings and transplanted into the test containers a few days prior to treatment.
(80) Depending on the species, the plants were kept at 10-25° C. or 20-35° C., respectively.
(81) The test period extended over 2 to 4 weeks. During this time, the plants were tended, and their response to the individual treatments was evaluated.
(82) Evaluation was carried out using a scale from 0 to 100. 100 means no emergence of the plants, or complete destruction of at least the aerial moieties, and 0 means no damage, or normal course of growth. A good herbicidal activity is given at values of at least 70 and a very good herbicidal activity is given at values of at least 85.
(83) The plants used in the greenhouse experiments were of the following species:
(84) TABLE-US-00007 Bayer code Scientific name ABUTH Abutilon theophrasti ALOMY Alopecurus myosuroides AMARE Amaranthus retroflexus APESV Apera spica-venti AVEFA Avena fatua ECHCG Echinocloa crus-galli SETVI Setaria viridis SETFA Setaria faberi POAAN Poa annua AGSST Agrostis stolonifera LOLMU Lolium multiflorum POLCO Polygonum convolvulus MATIN Matricaria inodora AGSST Agrostis stolonifera CHEAL Chenopodium album
(85) At an application rate of 1000 g/ha, Ex.1 applied by the post-emergence method showed very good herbicidal activity against ALOMY, and good herbicidal activity against AVEFA and ECHCG, and applied by the pre-emergence method showed very good herbicidal activity against APESV and ECHCG.
(86) At an application rate of 1000 g/ha, Ex.2 applied by the post-emergence method showed very good herbicidal activity against AVEFA and ALOMY, and good herbicidal activity against ECHCG, and applied by the pre-emergence method showed very good herbicidal activity against APESV and ECHCG.
(87) At an application rate of 2000 g/ha, Ex.4 applied by the post-emergence method showed very good herbicidal activity against SETVI, AVEFA and ALOMY, and applied by the pre-emergence method showed very good herbicidal activity against AGSST, APESV and ECHCG.
(88) At an application rate of 1819 g/ha, Ex.5 applied by the post-emergence method showed very good herbicidal activity against SETVI, AVEFA and ALOMY, and applied by the pre-emergence method showed very good herbicidal activity against APESV and ECHCG.
(89) At an application rate of 2000 g/ha, Ex.6 applied by the post-emergence method showed very good herbicidal activity against ECHCG and APESV, and applied by the pre-emergence method showed very good herbicidal activity against ECHCG and APESV.
(90) At an application rate of 2000 g/ha, Ex.7 applied by the post-emergence method showed good herbicidal activity against SETVI.
(91) At an application rate of 2000 g/ha, Ex.8 applied by the post-emergence method showed very good herbicidal activity against MATIN, ABUTH and AMARE.
(92) At an application rate of 1856 g/ha, Ex.9 applied by the post-emergence method showed very good herbicidal activity against ECHCG, AVEFA and ALOMY, and applied by the pre-emergence method showed very good herbicidal activity against APESV, and good herbicidal activity against ECHCG.
(93) At an application rate of 2000 g/ha, Ex.10 applied by the post-emergence method showed very good herbicidal activity against SETVI, ABUTH and AMARE, and applied by the pre-emergence method showed very good herbicidal activity against AGSST, MATIN and SETFA.
(94) At an application rate of 2000 g/ha, Ex.11 applied by the pre-emergence method showed very good herbicidal activity against SETFA and good herbicidal activity against ECHCG.
(95) At an application rate of 250 g/ha, Ex.13 applied by the post-emergence method showed very good herbicidal activity against ALOMY, ECHCG and POLCO, and applied by the pre-emergence method showed very good herbicidal activity against APESV.
(96) At an application rate of 250 g/ha, Ex.14 applied by the post-emergence method showed good herbicidal activity against LOLMU, and applied by the pre-emergence method showed very good herbicidal activity against APESV.
(97) At an application rate of 1000 g/ha, Ex.15 applied by the post-emergence method showed very good herbicidal activity against AVEFA and ALOMY, and good herbicidal activity against AMARE, and applied by the pre-emergence method showed very good herbicidal activity against APESV and ECHCG.
(98) At an application rate of 2000 g/ha, Ex.16 applied by the post-emergence method showed good herbicidal activity against AMARE, and applied by the pre-emergence method showed very good herbicidal activity against SETFA.
(99) At an application rate of 2000 g/ha, Ex.17 applied by the pre-emergence method showed very good herbicidal activity against AGSST, ECHCG and SETFA. At an application rate of 2000 g/ha, example 19 applied by the post-emergence method showed very good herbicidal activity against AMARE and ABUTH.
(100) At an application rate of 2000 g/ha, Ex.20 applied by the post-emergence method showed good herbicidal activity against AMARE and MATIN, and applied by the pre-emergence method showed good herbicidal activity against ECHCG.
(101) At an application rate of 1000 g/ha, Ex.21 applied by the post-emergence method showed very good herbicidal activity against ALOMY, and applied by the pre-emergence method showed very good herbicidal activity against APESV.
(102) At an application rate of 1000 g/ha, Ex.22 applied by the post-emergence method showed very good herbicidal activity against ALOMY, AVEFA and ECHCG, and applied by the pre-emergence method showed very good herbicidal activity against APESV.
(103) At an application rate of 2000 g/ha, Ex.24 applied by the post-emergence method showed very good herbicidal activity against ECHCG and SETVI, and applied by the pre-emergence method showed very good herbicidal activity against ECHCG and APESV.
(104) At an application rate of 2000 g/ha, Ex.25 applied by the post-emergence method showed very good herbicidal activity against MATIN, and applied by the pre-emergence method showed very good herbicidal activity against AGSST and POAAN.
(105) At an application rate of 2000 g/ha, Ex.26 applied by the post-emergence method showed very good herbicidal activity against ECHCG and ALOMY, and applied by the pre-emergence method showed very good herbicidal activity against APESV and ECHCG.
(106) At an application rate of 2000 g/ha, Ex.27 applied by the post-emergence method showed very good herbicidal activity against AMARE, ECHCG and ALOMY, and applied by the pre-emergence method showed very good herbicidal activity against AGSST, ECHCG and APESV.
(107) At an application rate of 1163 g/ha, Ex.28 applied by the post-emergence method, showed very good herbicidal activity against AMARE, and good herbicidal activity against ABUTH.
(108) At an application rate of 2000 g/ha, Ex.29 applied by the post-emergence method showed very good herbicidal activity against MATIN and AMARE.
(109) At an application rate of 2000 g/ha, Ex.30 applied by the post-emergence method showed very good herbicidal activity against SETVI and ALOMY, and applied by the pre-emergence method showed very good herbicidal activity against ECHCG and APESV.
(110) At an application rate of 2000 g/ha, Ex.31 applied by the post-emergence method showed very good herbicidal activity against SETVI and ALOMY, and applied by the pre-emergence method showed very good herbicidal activity against ECHCG and APESV.
(111) At an application rate of 2000 g/ha, Ex.32 applied by the post-emergence method, showed very good herbicidal activity against ALOMY, AVEFA and ECHCG, and applied by the pre-emergence method showed very good herbicidal activity against ECHCG and APESV.
(112) At an application rate of 2000 g/ha, Ex.33 applied by the post-emergence method showed good herbicidal activity against SETVI.
(113) At an application rate of 2000 g/ha, Ex.34 applied by the post-emergence method showed very good herbicidal activity against ECHCG, and good herbicidal activity against ALOMY, and applied by the pre-emergence method showed very good herbicidal activity against APESV, and good herbicidal activity against ECHCG.
(114) At an application rate of 2000 g/ha, Ex.35 applied by the post-emergence method showed very good herbicidal activity against AMARE, ECHCG and ALOMY, and applied by the pre-emergence method showed very good herbicidal activity against AGSST, ECHCG and APESV.
(115) At an application rate of 2000 g/ha, Ex.36 applied by the post-emergence method showed very good herbicidal activity against MATIN, and applied by the pre-emergence method showed very good herbicidal activity against AGSST and POAAN.
(116) At an application rate of 2000 g/ha, Ex.37 applied by the pre-emergence method showed good herbicidal activity against SETFA.
(117) At an application rate of 1000 g/ha, Ex.38 applied by the post-emergence method showed good herbicidal activity against SETVI.
(118) At an application rate of 2000 g/ha, Ex.39 applied by the post-emergence method showed very good herbicidal activity against AMARE and ABUTH, and applied by the pre-emergence method showed very good herbicidal activity against SETVI.
(119) At an application rate of 2000 g/ha, Ex.40 applied by the post-emergence method showed very good herbicidal activity against AVEFA and ALOMY, and applied by the pre-emergence method showed very good herbicidal activity against ECHCG and APESV.
(120) At an application rate of 2000 g/ha, Ex.41 applied by the post-emergence method showed very good herbicidal activity against MATIN and ALOMY.
(121) At an application rate of 1000 g/ha, Ex.42 applied by the post-emergence method showed very good herbicidal activity against SETVI.
(122) At an application rate of 1000 g/ha, Ex.44 applied by the post-emergence method showed very good herbicidal activity against AVEFA and ECHCG.
(123) At an application rate of 1000 g/ha, Ex.47 applied by the post-emergence method showed very good herbicidal activity against AMARE.
(124) At an application rate of 1000 g/ha, Ex.49 applied by the post-emergence method showed very good herbicidal activity against ALOMY and SETVI, and good herbicidal activity against ECHCG, and applied by the pre-emergence method showed good herbicidal activity against APESV and ECHCG.
(125) At an application rate of 500 g/ha, Ex.50 applied by the post-emergence method showed very good herbicidal activity against AMARE and SETVI.
(126) At an application rate of 1000 g/ha, Ex.51 applied by the post-emergence method showed very good herbicidal activity against SETVI.
(127) At an application rate of 1000 g/ha, Ex.52 applied by the post-emergence method showed very good herbicidal activity against SETVI.
(128) At an application rate of 1000 g/ha, Ex.54 applied by the post-emergence method showed very good herbicidal activity against AVEFA and ECHCG, and applied by the pre-emergence method showed very good herbicidal activity against APESV.
(129) At an application rate of 1000 g/ha, Ex.55 applied by the post-emergence method showed very good herbicidal activity against SETVI and AMARE.
(130) At an application rate of 1000 g/ha, Ex.58 applied by the post-emergence method showed very good herbicidal activity against SETVI, and good herbicidal activity against AVEFA.
(131) At an application rate of 1000 g/ha, Ex.59 applied by the post-emergence method showed very good herbicidal activity against SETVI, and good herbicidal activity against ECHCG, and applied by the pre-emergence method showed very good herbicidal activity against ECHCG, and good herbicidal activity against SETFA.
(132) At an application rate of 1000 g/ha, Ex.60 applied by the post-emergence method showed very good herbicidal activity against AVEFA and ALOMY.
(133) At an application rate of 500 g/ha, Ex.62 applied by the post-emergence method showed very good herbicidal activity against SETVI.
(134) At an application rate of 1000 g/ha, Ex.63 applied by the post-emergence method showed very good herbicidal activity against ECHCG.
(135) At an application rate of 2000 g/ha, Ex.65 applied by the post-emergence method showed very good herbicidal activity against AMARE and ECHCG.
(136) At an application rate of 2000 g/ha, Ex.66 applied by the post-emergence method showed very good herbicidal activity against ECHCG.
(137) At an application rate of 2000 g/ha, Ex.67 applied by the post-emergence method showed very good herbicidal activity against ALOMY and AVEFA, and good herbicidal activity against ECHCG, and applied by the pre-emergence method showed very good herbicidal activity against APESV.
(138) At an application rate of 2000 g/ha, Ex.70 applied by the post-emergence method showed very good herbicidal activity against ALOMY and SETVI.
(139) At an application rate of 2000 g/ha, Ex.71 applied by the post-emergence method showed very good herbicidal activity against ALOMY and AVEFA, and good herbicidal activity against ECHCG, and applied by the pre-emergence method showed very good herbicidal activity against ECHCG and APESV.
(140) At an application rate of 2000 g/ha, Ex.73 applied by the post-emergence method showed good herbicidal activity against ALOMY.
(141) At an application rate of 2000 g/ha, Ex.74 applied by the post-emergence method showed very good herbicidal activity against SETVI.
(142) At an application rate of 1000 g/ha, Ex.76 applied by the post-emergence method showed very good herbicidal activity against SETVI, and good herbicidal activity against ALOMY.
(143) At an application rate of 1000 g/ha, Ex.77 applied by the post-emergence method showed very good herbicidal activity against AVEFA and ALOMY.
(144) At an application rate of 1000 g/ha, Ex.78 applied by the post-emergence method showed very good herbicidal activity against SETVI.
(145) At an application rate of 1000 g/ha, Ex.79 applied by the post-emergence method showed very good herbicidal activity against AVEFA and ALOMY.
(146) At an application rate of 1000 g/ha, Ex.81 applied by the post-emergence method showed very good herbicidal activity against AVEFA and ALOMY.
(147) At an application rate of 2000 g/ha, Ex.85 applied by the post-emergence method showed very good herbicidal activity against ABUTH, and good herbicidal activity against AMARE.
(148) At an application rate of 1000 g/ha, Ex.86 applied by the post-emergence method showed very good herbicidal activity against SETVI, and good activity against ABUTH and AMARE, and applied by the pre-emergence method showed good herbicidal activity against APESV.
(149) At an application rate of 2000 g/ha, Ex.87 applied by the post-emergence method showed very good herbicidal activity against ALOMY, and applied by the pre-emergence method showed good herbicidal activity against AMARE.
(150) At an application rate of 2000 g/ha, Ex.88 applied by the post-emergence method showed very good herbicidal activity against SETVI.
(151) At an application rate of 2000 g/ha, Ex.89 applied by the post-emergence method showed very good herbicidal activity against ALOMY, and good activity against AVEFA, and applied by the pre-emergence method showed good herbicidal activity against APESV.
(152) At an application rate of 2000 g/ha, Ex.90 applied by the post-emergence method showed very good herbicidal activity against SETVI.
(153) At an application rate of 2000 g/ha, Ex.92 applied by the post-emergence method showed good herbicidal activity against ALOMY, SETVI and ECHCG.
(154) At an application rate of 2000 g/ha, Ex.93 applied by the post-emergence method showed very good herbicidal activity against ALOMY, AVEFA and ECHCG, and applied by the pre-emergence method showed very good herbicidal activity against APESV and ECHCG.
(155) At an application rate of 2000 g/ha, Ex.94 applied by the post-emergence method showed very good herbicidal activity against ALOMY and AVEFA, and applied by the pre-emergence method showed very good herbicidal activity against APESV.
(156) At an application rate of 2000 g/ha, Ex.95 applied by the post-emergence method showed very good herbicidal activity against ALOMY and ECHCG, and applied by the pre-emergence method showed very good herbicidal activity against APESV.
(157) At an application rate of 1000 g/ha, Ex.96 applied by the post-emergence method showed very good herbicidal activity against SETVI.
(158) At an application rate of 2000 g/ha, Ex.97 applied by the post-emergence method showed very good herbicidal activity against ECHCG, and applied by the pre-emergence method showed very good herbicidal activity against APESV.
(159) At an application rate of 500 g/ha, Ex.98 applied by the post-emergence method showed good herbicidal activity against SETVI.
(160) At an application rate of 2000 g/ha, Ex.99 applied by the post-emergence method showed very good herbicidal activity against SETVI.
(161) At an application rate of 2000 g/ha, Ex.101 applied by the post-emergence method showed very good herbicidal activity against ABUTH, and AMARE.
(162) At an application rate of 2000 g/ha, Ex.102 applied by the post-emergence method showed very good herbicidal activity against ECHCG.
(163) At an application rate of 2000 g/ha, Ex.103 applied by the post-emergence method showed very good herbicidal activity against SETVI.
(164) At an application rate of 2000 g/ha, Ex.104 applied by the post-emergence method showed very good herbicidal activity against ALOMY, and good herbicidal activity against ECHCG, and applied by the pre-emergence method showed very good herbicidal activity against APESV, and good herbicidal activity against ECHCG.
(165) At an application rate of 2000 g/ha, Ex.105 applied by the post-emergence method showed very good herbicidal activity against APESV, and ECHCG, and applied by the pre-emergence method showed very good herbicidal activity against ALOMY, and ECHCG.
(166) At an application rate of 2000 g/ha, Ex.106 applied by the post-emergence method showed very good herbicidal activity against ALOMY, AVEFA, and ECHCG, and applied by the pre-emergence method showed very good herbicidal activity against APESV, and ECHCG.
(167) At an application rate of 500 g/ha, Ex.108 applied by the post-emergence method showed good herbicidal activity against ALOMY, and showed very good herbicidal activity against POLCO.
(168) At an application rate of 1000 g/ha, Ex.110 applied by the post-emergence method showed good herbicidal activity against ECHCG.
(169) At an application rate of 1000 g/ha, Ex. 112 applied by the post-emergence method showed good herbicidal activity against ECHCG.
(170) At an application rate of 500 g/ha, Ex.1 14 applied by the post-emergence method showed very good herbicidal activity against SETVI.
(171) At an application rate of 1000 g/ha, Ex.119 applied by the post-emergence method showed good herbicidal activity against SETVI, and showed very good herbicidal activity against ALOMY.
(172) At an application rate of 1000 g/ha, Ex.120 applied by the post-emergence method showed good herbicidal activity against ALOMY.
(173) At an application rate of 500 g/ha, Ex.121 applied by the post-emergence method showed very good herbicidal activity against LOLMU, ECHCG, POLCO and ALOMY.
(174) At an application rate of 2000 g/ha, Ex.123 applied by the post-emergence method showed good herbicidal activity against SETVI, and very good herbicidal activity against AMARE.
(175) At an application rate of 500 g/ha, Ex.125 applied by the post-emergence method showed very good herbicidal activity against ECHCG.
(176) At an application rate of 2000 g/ha, Ex.126 applied by the post-emergence method showed very good herbicidal activity against ECHCG.
(177) At an application rate of 2000 g/ha, Ex.127 applied by the post-emergence method showed very good herbicidal activity against AMARE.
(178) At an application rate of 2000 g/ha, Ex.128 applied by the post-emergence method showed very good herbicidal activity against AVEFA, and ECHCG, and good herbicidal activity against ALOMY, and applied by the pre-emergence method showed very good herbicidal activity against APESV.
(179) At an application rate of 2000 g/ha, Ex.129 applied by the post-emergence method showed very good herbicidal activity against AMARE, ALOMY, and ECHCG, and applied by the pre-emergence method showed very good herbicidal activity against APESV.
(180) At an application rate of 2000 g/ha, Ex.131 applied by the post-emergence method showed very good herbicidal activity against AMARE, and ECHCG.
(181) At an application rate of 2000 g/ha, Ex.132 applied by the post-emergence method showed very good herbicidal activity against ECHCG, and good herbicidal activity against AMARE.
(182) At an application rate of 500 g/ha, Ex.135 applied by the post-emergence method showed good herbicidal activity against ALOMY.
(183) At an application rate of 1000 g/ha, Ex.141 applied by the post-emergence method showed good herbicidal activity against SETVI.
(184) At an application rate of 2000 g/ha, Ex.143 applied by the post-emergence method showed very good herbicidal activity against ECHCG.
(185) At an application rate of 2000 g/ha, Ex.146 applied by the post-emergence method showed very good herbicidal activity against ABUTH, SETVI and ECHCG, and applied by the pre-emergence method showed very good herbicidal activity against APESV, and ECHCG.
(186) At an application rate of 2000 g/ha, Ex.147 applied by the post-emergence method showed very good herbicidal activity against ALOMY, AVEFA, and ECHCG, and applied by the pre-emergence method showed very good herbicidal activity against APESV, and ECHCG.
(187) At an application rate of 2000 g/ha, Ex.150 applied by the post-emergence method showed very good herbicidal activity against AMARE and ECHCG, and good herbicidal activity against ALOMY, and applied by the pre-emergence method showed very good herbicidal activity against APESV, and good herbicidal activity against ECHCG.
(188) At an application rate of 2000 g/ha, Ex.153 applied by the post-emergence method showed very good herbicidal activity against ALOMY, AVEFA, and ECHCG, and applied by the pre-emergence method showed very good herbicidal activity against APESV, and ECHCG.
(189) At an application rate of 2000 g/ha, Ex.154 applied by the post-emergence method showed very good herbicidal activity against ALOMY, AVEFA, and ECHCG, and applied by the pre-emergence method showed very good herbicidal activity against APESV, and ECHCG.
(190) At an application rate of 2000 g/ha, Ex.155 applied by the post-emergence method showed very good herbicidal activity against ALOMY, and ECHCG.
(191) At an application rate of 2000 g/ha, Ex.157 applied by the post-emergence method showed very good herbicidal activity against ALOMY, AVEFA and ECHCG, and applied by the pre-emergence method showed very good herbicidal activity against APESV, and ECHCG.
(192) At an application rate of 2000 g/ha, Ex.159 applied by the post-emergence method showed very good herbicidal activity against ALOMY and AVEFA, and applied by the pre-emergence method showed good herbicidal activity against APESV, and ECHCG.
(193) At an application rate of 2000 g/ha, Ex.164 applied by the post-emergence method showed very good herbicidal activity against AMARE.
(194) At an application rate of 2000 g/ha, Ex.211 applied by the post-emergence method showed good herbicidal activity against ALOMY and very good herbicidal activity against ECHCG, and applied by the pre-emergence method showed good herbicidal activity against APESV, and POAAN.
(195) At an application rate of 2000 g/ha, Ex.213 applied by the post-emergence method showed very good herbicidal activity against ALOMY, AFEFA and ECHCG, and applied by the pre-emergence method showed good herbicidal activity against APESV, ECHCG and POAAN.
(196) At an application rate of 2000 g/ha, Ex.214 applied by the post-emergence method showed very good herbicidal activity against ALOMY, AMARE and ECHCG, and applied by the pre-emergence method showed good herbicidal activity against APESV and ECHCG, and good herbicidal activity against POAAN.
(197) At an application rate of 2000 g/ha, Ex.215 applied by the post-emergence method showed very good herbicidal activity against ALOMY and applied by the pre-emergence method showed very good herbicidal activity against APESV.
(198) At an application rate of 1000 g/ha, Ex.216 applied by the post-emergence method showed very good herbicidal activity against ALOMY and ECHCG, and applied by the pre-emergence method showed very good herbicidal activity against APESV.
(199) At an application rate of 1000 g/ha, Ex.219 applied by the post-emergence method showed good herbicidal activity against SETVI.
(200) At an application rate of 1000 g/ha, Ex.220 applied by the pre-emergence method showed good herbicidal activity against ECHCG.
(201) At an application rate of 2000 g/ha, Ex.221 applied by the post-emergence method showed very good herbicidal activity against ABUTH, AGSST and ECHCG, and applied by the pre-emergence method showed very good herbicidal activity against APESV, ECHCG and POAAN.
(202) At an application rate of 2000 g/ha, Ex.222 applied by the post-emergence method showed very good herbicidal activity against ABUTH, AMARE and MATIN.
(203) At an application rate of 2000 g/ha, Ex.223 applied by the post-emergence method showed very good herbicidal activity against ABUTH, AMARE and ECHCG, and applied by the pre-emergence method showed very good herbicidal activity against APESV, ECHCG and POAAN.
(204) At an application rate of 2000 g/ha, Ex.224 applied by the post-emergence method showed very good herbicidal activity against ALOMY and ECHCG, and applied by the pre-emergence method showed very good herbicidal activity against APESV and ECHCG.
(205) At an application rate of 2000 g/ha, Ex.225 applied by the post-emergence method showed very good herbicidal activity against ALOMY, AVEFA and ECHCG, and applied by the pre-emergence method showed very good herbicidal activity against APESV, ECHCG and POAAN.
(206) At an application rate of 500 g/ha, Ex.226 applied by the post-emergence method showed very good herbicidal activity against AMARE.
(207) At an application rate of 1000 g/ha, Ex.228 applied by the post-emergence method showed good herbicidal activity against ABUTH and ECHCG, and applied by the pre-emergence method showed very good herbicidal activity against APESV.
(208) At an application rate of 1000 g/ha, Ex.229 applied by the pre-emergence method showed very good herbicidal activity against APESV and good herbicidal activity against AMARE.
(209) At an application rate of 2000 g/ha, Ex.230 applied by the post-emergence method showed good herbicidal activity against MATIN.
(210) At an application rate of 2000 g/ha, Ex.231 applied by the post-emergence method showed very good herbicidal activity against ECHCG and good herbicidal activity against MATIN.
(211) At an application rate of 2000 g/ha, Ex.232 applied by the post-emergence method showed very good herbicidal activity against AMARE.
(212) At an application rate of 2000 g/ha, Ex.233 applied by the pre-emergence method showed very good herbicidal activity against AMARE.
(213) At an application rate of 2000 g/ha, Ex.234 applied by the post-emergence method showed good herbicidal activity against POAAN, and applied by the pre-emergence method showed very good herbicidal activity against APESV.
(214) At an application rate of 2000 g/ha, Ex.236 applied by the post-emergence method showed very good herbicidal activity against ALOMY, AVEFA and ECHCG, and applied by the pre-emergence method showed very good herbicidal activity against APESV and ECHCG.
(215) At an application rate of 2000 g/ha, Ex.237 applied by the post-emergence method showed very good herbicidal activity against ALOMY, AVEFA and ECHCG, and applied by the pre-emergence method showed very good herbicidal activity against APESV and ECHCG.
(216) At an application rate of 2000 g/ha, Ex.238 applied by the post-emergence method showed good herbicidal activity against ALOMY, and very good herbicidal activity against ALOMY, AMARE and ECHCG.
(217) At an application rate of 2000 g/ha, Ex.240 applied by the pre-emergence method showed very good herbicidal activity against APESV and ECHCG.
(218) At an application rate of 2000 g/ha, Ex.241 applied by the post-emergence method showed good herbicidal activity against ECHCG, and applied by the pre-emergence method showed very good herbicidal activity against APESV and POAAN.
(219) At an application rate of 1000 g/ha, Ex.243 applied by the post-emergence method showed very good herbicidal activity against ALOMY, AVEFA and ECHCG, and applied by the pre-emergence method showed very good herbicidal activity against APESV and ECHCG.
(220) At an application rate of 500 g/ha, Ex.244 applied by the post-emergence method showed good herbicidal activity against ALOMY, POAAN, and POLCO, and applied by the pre-emergence method showed very good herbicidal activity against APESV, ECHCG and POAAN.
(221) At an application rate of 1000 g/ha, Ex.245 applied by the post-emergence method showed very good herbicidal activity against ALOMY, AVEFA and ECHCG, and applied by the pre-emergence method showed very good herbicidal activity against APESV and good herbicidal activity against ECHCG.
(222) At an application rate of 500 g/ha, Ex.246 applied by the pre-emergence method showed very good herbicidal activity against AMARE.
(223) At an application rate of 500 g/ha, Ex.247 applied by the post-emergence method showed very good herbicidal activity against ALOMY, AGSST, and AMARE, and applied by the pre-emergence method showed very good herbicidal activity against APESV, ECHCG and POAAN.
(224) At an application rate of 2000 g/ha, Ex.248 applied by the post-emergence method showed very good herbicidal activity against ALOMY, ECHCG, and SETVI, and applied by the pre-emergence method showed very good herbicidal activity against APESV, ECHCG and POAAN.
(225) At an application rate of 2000 g/ha, Ex.250 applied by the post-emergence method showed very good herbicidal activity against ALOMY, AVEFA and ECHCG, and applied by the pre-emergence method showed very good herbicidal activity against APESV and ECHCG.
(226) At an application rate of 500 g/ha, Ex.251 applied by the pre-emergence method showed very good herbicidal activity against AMARE.
(227) At an application rate of 1000 g/ha, Ex.252 applied by the post-emergence method showed very good herbicidal activity against ABUTH.
(228) At an application rate of 1000 g/ha, Ex.253 applied by the post-emergence method showed very good herbicidal activity against ALOMY and AMARE, and good herbicidal activity against ABUTH.
(229) At an application rate of 1000 g/ha, Ex.254 applied by the post-emergence method showed very good herbicidal activity against ECHCG and AMARE, and good herbicidal activity against ALOMY.
(230) At an application rate of 500 g/ha, Ex.255 applied by the post-emergence method showed good herbicidal activity against AMARE.
(231) At an application rate of 2000 g/ha, Ex.256 applied by the post-emergence method showed very good herbicidal activity against ECHCG, and applied by the pre-emergence method showed very good herbicidal activity against APESV and ECHCG.
(232) At an application rate of 2000 g/ha, Ex.257 applied by the post-emergence method showed good herbicidal activity against MATIN.
(233) At an application rate of 2000 g/ha, Ex.259 applied by the post-emergence method showed very good herbicidal activity against ALOMY, POAAN and ECHCG, and applied by the pre-emergence method showed good herbicidal activity against APESV and ECHCG.
(234) At an application rate of 2000 g/ha, Ex.260 applied by the post-emergence method showed very good herbicidal activity against ALOMY, and good herbicidal activity against AVEFA and ECHCG, and applied by the pre-emergence method showed very good herbicidal activity against ECHCG and MATIN, and good herbicidal activity against APESV.
(235) At an application rate of 1000 g/ha, Ex.261 applied by the post-emergence method showed very good herbicidal activity against ALOMY, AVEFA and ECHCG, and applied by the pre-emergence method showed very good herbicidal activity against APESV and ECHCG.
(236) At an application rate of 1000 g/ha, Ex.262 applied by the post-emergence method showed very good herbicidal activity against AMARE, SETVI and ECHCG, and applied by the pre-emergence method showed very good herbicidal activity against APESV and ECHCG.
(237) At an application rate of 1000 g/ha, Ex.263 applied by the post-emergence method showed very good herbicidal activity against ALOMY, AVEFA and ECHCG, and applied by the pre-emergence method showed very good herbicidal activity against APESV and ECHCG.
(238) At an application rate of 500 g/ha, Ex.264 applied by the post-emergence method showed very good herbicidal activity against ALOMY and AVEFA.
(239) At an application rate of 250 g/ha, Ex.265 applied by the post-emergence method showed good herbicidal activity against ALOMY and CHEAL, and very good herbicidal activity against AMARE.
(240) At an application rate of 1000 g/ha, Ex.266 applied by the post-emergence method showed very good herbicidal activity against ALOMY, AMARE and ABUTH, and applied by the pre-emergence method showed very good herbicidal activity against APESV and ECHCG.
(241) At an application rate of 2000 g/ha, Ex.267 applied by the post-emergence method showed very good herbicidal activity against ECHCG, POAAN and ABUTH, and applied by the pre-emergence method showed very good herbicidal activity against POAAN and ECHCG.
(242) At an application rate of 1000 g/ha, Ex.268 applied by the post-emergence method showed very good herbicidal activity against ECHCG, and applied by the pre-emergence method showed very good herbicidal activity against POAAN and ECHCG.
(243) At an application rate of 1000 g/ha, Ex.269 applied by the post-emergence method showed very good herbicidal activity against ECHCG, and applied by the pre-emergence method showed very good herbicidal activity against SETFA.
(244) At an application rate of 1000 g/ha, Ex.270 applied by the post-emergence method showed very good herbicidal activity against ALOMY and ECHCG, and applied by the pre-emergence method showed very good herbicidal activity against APESV and ECHCG.
(245) At an application rate of 1000 g/ha, Ex.271 applied by the post-emergence method showed good herbicidal activity against ECHCG, very good herbicidal activity against SETVI.
(246) At an application rate of 2000 g/ha, Ex.272 applied by the post-emergence method showed very good herbicidal activity against ALOMY, AVEFA and SETVI, and applied by the pre-emergence method showed very good herbicidal activity against APESV and ECHCG.
(247) At an application rate of 1000 g/ha, Ex.273 applied by the post-emergence method showed very good herbicidal activity against ALOMY, AMARE and SETVI, and applied by the pre-emergence method showed very good herbicidal activity against APESV and ECHCG.
(248) At an application rate of 1000 g/ha, Ex.274 applied by the post-emergence method showed very good herbicidal activity against ALOMY and ECHCG, and applied by the pre-emergence method showed very good herbicidal activity against APESV and ECHCG.
(249) At an application rate of 1000 g/ha, Ex.276 applied by the post-emergence method showed very good herbicidal activity against ALOMY, AMARE and ABUTH, and applied by the pre-emergence method showed very good herbicidal activity against APESV.
(250) At an application rate of 1000 g/ha, Ex.277 applied by the post-emergence method showed very good herbicidal activity against ALOMY, SETVI and ECHCG, and applied by the pre-emergence method showed very good herbicidal activity against APESV and ECHCG.
(251) At an application rate of 1000 g/ha, Ex.278 applied by the post-emergence method showed very good herbicidal activity against AMARE, ABUTH and ECHCG, and applied by the pre-emergence method showed very good herbicidal activity against APESV and ECHCG.
(252) At an application rate of 1000 g/ha, Ex.279 applied by the post-emergence method showed very good herbicidal activity against AMARE, ABUTH and ALOMY, and applied by the pre-emergence method showed very good herbicidal activity against APESV and ECHCG.
(253) At an application rate of 2000 g/ha, Ex.281 applied by the post-emergence method showed good herbicidal activity against AMARE, ABUTH and ALOMY, and very good herbicidal activity against ABUTH.
(254) At an application rate of 2000 g/ha, Ex.282 applied by the post-emergence method showed very good herbicidal activity against ALOMY, AVEFA and SETVI, and applied by the pre-emergence method showed very good herbicidal activity against APESV and ECHCG.
(255) At an application rate of 2000 g/ha, Ex.283 applied by the post-emergence method showed very good herbicidal activity against ALOMY, AVEFA and ECHCG, and applied by the pre-emergence method showed very good herbicidal activity against APESV and good herbicidal activity against ECHCG.
(256) At an application rate of 2000 g/ha, Ex.284 applied by the post-emergence method showed very good herbicidal activity against ALOMY, AVEFA and ECHCG, and applied by the pre-emergence method showed very good herbicidal activity against APESV and ECHCG.
(257) At an application rate of 1000 g/ha, Ex.285 applied by the post-emergence method showed very good herbicidal activity against ALOMY, AMARE and ABUTH, and applied by the pre-emergence method showed very good herbicidal activity against APESV and ECHCG.
(258) At an application rate of 1000 g/ha, Ex.286 applied by the post-emergence method showed very good herbicidal activity against ECHCG, AMARE and ABUTH, and applied by the pre-emergence method showed very good herbicidal activity against AMARE, APESV and ECHCG.
(259) At an application rate of 1000 g/ha, Ex.287 applied by the post-emergence method showed very good herbicidal activity against ALOMY, AVEFA and ECHCG, and applied by the pre-emergence method showed very good herbicidal activity against APESV and ECHCG.
(260) At an application rate of 2000 g/ha, Ex.288 applied by the post-emergence method showed very good herbicidal activity against ALOMY.
(261) At an application rate of 2000 g/ha, Ex.289 applied by the post-emergence method showed very good herbicidal activity against ALOMY, AMARE and SETVI, and applied by the pre-emergence method showed very good herbicidal activity against APESV and ECHCG.
(262) At an application rate of 2000 g/ha, Ex.290 applied by the post-emergence method showed very good herbicidal activity against ALOMY, AVEFA and ECHCG, and applied by the pre-emergence method showed very good herbicidal activity against APESV and ECHCG.
(263) At an application rate of 500 g/ha, Ex.291 applied by the post-emergence method showed good herbicidal activity against ALOMY, AVEFA and LOLMU, and applied by the pre-emergence method showed very good herbicidal activity against POAAN, APESV and ECHCG.
(264) At an application rate of 1000 g/ha, Ex.292 applied by the post-emergence method showed very good herbicidal activity against ECHCG and SETVI, and good herbicidal activity against ALOMY, and applied by the pre-emergence method showed very good herbicidal activity against APESV and ECHCG.
(265) At an application rate of 1000 g/ha, Ex.293 applied by the post-emergence method showed good herbicidal activity against ABUTH, and applied by the pre-emergence method showed very good herbicidal activity against SETFA, and good herbicidal activity against ECHCG.
(266) At an application rate of 2000 g/ha, Ex.294 applied by the post-emergence method showed very good herbicidal activity against ALOMY, ABUTH and ECHCG, and applied by the pre-emergence method showed good herbicidal activity against APESV.
(267) At an application rate of 2000 g/ha, Ex.295 applied by the post-emergence method showed very good herbicidal activity against ALOMY and AVEFA, and applied by the pre-emergence method showed very good herbicidal activity against APESV, AMARE and ECHCG.
(268) At an application rate of 1000 g/ha, Ex.296 applied by the post-emergence method showed very good herbicidal activity against ABUTH.
(269) At an application rate of 2000 g/ha, Ex.297 applied by the post-emergence method showed very good herbicidal activity against ALOMY, ECHCG and AVEFA, and applied by the pre-emergence method showed very good herbicidal activity against APESV, and good herbicidal activity against ECHCG and ABUTH.
(270) At an application rate of 1000 g/ha, Ex.309 applied by the post-emergence method showed very good herbicidal activity against ALOMY, ECHCG and AMARE, and very good herbicidal activity against APESV.
(271) At an application rate of 500 g/ha, Ex.310 applied by the post-emergence method showed very good herbicidal activity against ALOMY, AMARE and POLCO, and very good herbicidal activity against ALOMY, ECHCG and APESV.
(272) At an application rate of 500 g/ha, Ex.311 applied by the post-emergence method showed very good herbicidal activity against ALOMY, AMARE and POLCO, and very good herbicidal activity against ALOMY, ECHCG and APESV.
(273) At an application rate of 500 g/ha, Ex.312 applied by the post-emergence method showed very good herbicidal activity against ALOMY, ECHCG and POLCO, and very good herbicidal activity against ALOMY, ECHCG and APESV.
(274) At an application rate of 1000 g/ha, Ex.313 applied by the post-emergence method showed very good herbicidal activity against ALOMY, ECHCG and SETVI, and very good herbicidal activity against ECHCG and APESV.
(275) At an application rate of 1000 g/ha, Ex.314 applied by the post-emergence method showed very good herbicidal activity against AMARE, ECHCG and SETVI, and very good herbicidal activity against ECHCG and APESV.
(276) At an application rate of 2000 g/ha, Ex.315 applied by the post-emergence method showed very good herbicidal activity against AMARE, ECHCG and ALOMY, and very good herbicidal activity against ECHCG and APESV.