2-Amino-5-keto-pyrimidine derivatives and the use thereof for controlling undesired plant growth

Abstract

What are described are compounds of the general formula (I) and agrochemically acceptable salts thereof

##STR00001##

and the use thereof in the crop protection sector.

Claims

1. A compound of formula (I) ##STR00015## And/or an agrochemically acceptable salt thereof in which R.sup.1 is selected from the group consisting of (C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-haloalkyl, (C.sub.1-C.sub.6)-alkylcarbonyl-(C.sub.1-C.sub.4)-alkyl; (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.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; tri-(C.sub.1-C.sub.6)-alkylsilyl-(C.sub.2-C.sub.6)-alkynyl, di-(C.sub.1-C.sub.6)-alkylsilyl-(C.sub.2-C.sub.6)-alkynyl, mono-(C.sub.1-C.sub.6)-alkylsilyl-(C.sub.2-C.sub.6)-alkynyl; phenylsilyl-(C.sub.2-C.sub.6)-alkynyl; (C.sub.6-C.sub.14)-aryl which may be substituted in the aryl moiety in each case by halogen, (C.sub.1-C.sub.6)-alkyl and/or (C.sub.1-C.sub.6)-haloalkyl; (C.sub.6-C.sub.14)-aryl-(C.sub.1-C.sub.6)-alkyl; aminocarbonyl-(C.sub.1-C.sub.6)-alkyl; (C.sub.1-C.sub.6)-alkoxy-(C.sub.1-C.sub.6)-alkyl; (C.sub.3-C.sub.8)-cycloalkyl which may optionally be substituted in the cycloalkyl radical by (C.sub.1-C.sub.6)-alkyl and/or halogen; (C.sub.3-C.sub.8)-cycloalkyl-(C.sub.1-C.sub.6)-alkyl, (C.sub.3-C.sub.8)-cycloalkyl-(C.sub.1-C.sub.6)-haloalkyl (C.sub.3-C.sub.8)-cycloalkenyl, (C.sub.3-C.sub.85)-cycloalkenyl-(C.sub.1-C.sub.6)-alkyl, (C.sub.3-C.sub.8)-cycloalkenyl-(C.sub.1-C.sub.6)-haloalkyl, hydroxy-(C.sub.1-C.sub.6)-alkyl, cyano-(C.sub.1-C.sub.6)-alkyl; (C.sub.1-C.sub.6)-alkylsulfonyl-(C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-alkylthio-(C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-alkylsulfinyl-(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)-haloalkylthio-(C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-haloalkylsulfinyl-(C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-alkylsulfonyl-(C.sub.1-C.sub.6)-haloalkyl, (C.sub.1-C.sub.6)-alkylthio-(C.sub.1-C.sub.6)-haloalkyl, (C.sub.1-C.sub.6)-alkylsulfinyl-(C.sub.1-C.sub.6)-haloalkyl, (C.sub.1-C.sub.6)-haloalkylsulfonyl-(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)-haloalkylsulfinyl-(C.sub.1-C.sub.6)-haloalkyl, and R.sup.2a and R.sup.2b are each independently selected from the group consisting of hydrogen, halogen, hydroxyl, cyano, nitro, C(O)OH, C(O)NH.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.1-C.sub.6)-haloalkylcarbonyl, (C.sub.1-C.sub.6)-alkylcarbonyloxy, (C.sub.1-C.sub.6)-haloalkylcarbonyloxy, (C.sub.1-C.sub.6)-alkylcarbonyl-(C.sub.1-C.sub.4)-alkyl; (C.sub.1-C.sub.6)-alkoxy, (C.sub.1-C.sub.6)-haloalkoxy, (C.sub.1-C.sub.6)-alkoxycarbonyl, (C.sub.1-C.sub.6)-haloalkoxycarbonyl, (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.2-C.sub.6)-alkenyl, (C.sub.2-C.sub.6)-haloalkenyl, (C.sub.2-C.sub.6)-alkenylcarbonyl, (C.sub.2-C.sub.6)-haloalkenylcarbonyl, (C.sub.2-C.sub.6)-alkenyloxy, (C.sub.2-C.sub.6)-haloalkenyloxy, (C.sub.2-C.sub.6)-alkenyloxycarbonyl, (C.sub.2-C.sub.6)-haloalkenyloxycarbonyl; (C.sub.2-C.sub.6)-alkynyl, (C.sub.2-C.sub.6)-haloalkynyl, (C.sub.2-C.sub.6)-alkynylcarbonyl, (C.sub.2-C.sub.6)-haloalkynylcarbonyl, (C.sub.2-C.sub.6)-alkynyloxy, (C.sub.2-C.sub.6)-haloalkynyloxy, (C.sub.2-C.sub.6)-alkynyloxycarbonyl, (C.sub.2-C.sub.6)-haloalkynyloxycarbonyl; tri-(C.sub.1-C.sub.6)-alkylsilyl-(C.sub.2-C.sub.6)-alkynyl, di-(C.sub.1-C.sub.6)-alkylsilyl-(C.sub.2-C.sub.6)-alkynyl, mono-(C.sub.1-C.sub.6)-alkylsilyl-(C.sub.2-C.sub.6)-alkynyl; phenylsilyl-(C.sub.2-C.sub.6)-alkynyl; (C.sub.6-C.sub.14)-aryl, (C.sub.6-C.sub.14)-aryloxy, (C.sub.6-C.sub.14)-arylcarbonyl and (C.sub.6-C.sub.14)-aryloxycarbonyl, each of which may be substituted in the aryl moiety by halogen, (C.sub.1-C.sub.6)-alkyl and/or (C.sub.1-C.sub.6)-haloalkyl; (C.sub.6-C.sub.14)-aryl-(C.sub.1-C.sub.6)-alkyl, (C.sub.6-C.sub.14)-aryl-(C.sub.1-C.sub.6)-alkoxy, (C.sub.6-C.sub.14)-aryl-(C.sub.1-C.sub.6)-alkylcarbonyl, (C.sub.6-C.sub.14)-aryl-(C.sub.1-C.sub.6)-alkylcarbonyloxy, (C.sub.6-C.sub.14)-aryl-(C.sub.1-C.sub.6)-alkoxycarbonyl, (C.sub.6-C.sub.14)-aryl-(C.sub.1-C.sub.6)-alkoxycarbonyloxy; aminocarbonyl-(C.sub.1-C.sub.6)-alkyl, di-(C.sub.1-C.sub.6)-alkylaminocarbonyl-(C.sub.1-C.sub.6)-alkyl; N((C.sub.1-C.sub.6)-haloalkanoyl)-aminocarbonyl, mono-((C.sub.6-C.sub.14)-aryl)-aminocarbonyl, di-((C.sub.6-C.sub.14)-aryl)-aminocarbonyl; (C.sub.1-C.sub.6)-alkoxy-(C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-alkoxy-(C.sub.1-C.sub.6)-alkoxy, (C.sub.1-C.sub.6)-alkoxycarbonyl-(C.sub.1-C.sub.6)-alkoxy; (C.sub.3-C.sub.8)-cycloalkyl which may optionally be substituted in the cycloalkyl radical by (C.sub.1-C.sub.6)-alkyl and/or halogen; (C.sub.3-C.sub.8)-cycloalkoxy, (C.sub.3-C.sub.8)-cycloalkyl-(C.sub.1-C.sub.6)-alkyl, (C.sub.3-C.sub.8)-cycloalkyl-(C.sub.1-C.sub.6)-haloalkyl, (C.sub.3-C.sub.8)-cycloalkyl-(C.sub.1-C.sub.6)-alkoxy, (C.sub.3-C.sub.8)-cycloalkyl-(C.sub.1-C.sub.6)-haloalkoxy, (C.sub.3-C.sub.8)-cycloalkylcarbonyl, (C.sub.3-C.sub.8)-cycloalkoxycarbonyl, (C.sub.3-C.sub.8)-cycloalkyl-(C.sub.1-C.sub.6)-alkylcarbonyl, (C.sub.3-C.sub.8)-cycloalkyl-(C.sub.1-C.sub.6)-haloalkylcarbonyl, (C.sub.3-C.sub.8)-cycloalkyl-(C.sub.1-C.sub.6)-alkoxycarbonyl, (C.sub.3-C.sub.8)-cycloalkyl-(C.sub.1-C.sub.6)-haloalkoxycarbonyl, (C.sub.3-C.sub.8)-cycloalkylcarbonyloxy, (C.sub.3-C.sub.8)-cycloalkoxycarbonyloxy, (C.sub.3-C.sub.8)-cycloalkyl-(C.sub.1-C.sub.6)-alkylcarbonyloxy, (C.sub.3-C.sub.8)-cycloalkyl-(C.sub.1-C.sub.6)-haloalkylcarbonyloxy, (C.sub.3-C.sub.8)-cycloalkyl-(C.sub.1-C.sub.6)-alkoxycarbonyloxy, (C.sub.3-C.sub.8)-cycloalkyl-(C.sub.1-C.sub.6)-haloalkoxycarbonyloxy; (C.sub.3-C.sub.8)-cycloalkenyl, (C.sub.3-C.sub.8)-cycloalkenyloxy, (C.sub.3-C.sub.8)-cycloalkenyl-(C.sub.1-C.sub.6)-alkyl, (C.sub.3-C.sub.8)-cycloalkenyl-(C.sub.1-C.sub.6)-haloalkyl, (C.sub.3-C.sub.8)-cycloalkenyl-(C.sub.1-C.sub.6)-alkoxy, (C.sub.3-C.sub.8)-cycloalkenyl-(C.sub.1-C.sub.6)-haloalkoxy, (C.sub.3-C.sub.8)-cycloalkenylcarbonyl, (C.sub.3-C.sub.8)-cycloalkenyloxycarbonyl, (C.sub.3-C.sub.8)-cycloalkenyl-(C.sub.1-C.sub.6)-alkylcarbonyl, (C.sub.3-C.sub.8)-cycloalkenyl-(C.sub.1-C.sub.6)-haloalkylcarbonyl, (C.sub.3-C.sub.8)-cycloalkenyl-(C.sub.1-C.sub.6)-alkoxycarbonyl, (C.sub.3-C.sub.8)-cycloalkenyl-(C.sub.1-C.sub.6)-haloalkoxycarbonyl, (C.sub.3-C.sub.8)-cycloalkenylcarbonyloxy, (C.sub.3-C.sub.8)-cycloalkenyloxycarbonyloxy, (C.sub.3-C.sub.8)-cycloalkenyl-(C.sub.1-C.sub.6)-alkylcarbonyloxy, (C.sub.3-C.sub.8)-cycloalkenyl-(C.sub.1-C.sub.6)-haloalkylcarbonyloxy, (C.sub.3-C.sub.8)-cycloalkenyl-(C.sub.1-C.sub.6)-alkoxycarbonyloxy, (C.sub.3-C.sub.8)-cycloalkenyl-(C.sub.1-C.sub.6)-haloalkoxycarbonyloxy; hydroxy-(C.sub.1-C.sub.6)-alkyl, hydroxy-(C.sub.1-C.sub.6)-alkoxy, cyano-(C.sub.1-C.sub.6)-alkoxy, cyano-(C.sub.1-C.sub.6)-alkyl; (C.sub.1-C.sub.6)-alkylsulfonyl, (C.sub.1-C.sub.6)-alkylthio, (C.sub.1-C.sub.6)-alkylsulfinyl, (C.sub.1-C.sub.6)-haloalkylsulfonyl, (C.sub.1-C.sub.6)-haloalkylthio, (C.sub.1-C.sub.6)-haloalkylsulfinyl, (C.sub.1-C.sub.6)-alkylsulfonyl-(C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-alkylthio-(C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-alkylsulfinyl-(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)-haloalkylthio-(C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-haloalkylsulfinyl-(C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-alkylsulfonyl-(C.sub.1-C.sub.6)-haloalkyl, (C.sub.1-C.sub.6)-alkylthio-(C.sub.1-C.sub.6)-haloalkyl, (C.sub.1-C.sub.6)-alkylsulfinyl-(C.sub.1-C.sub.6)-haloalkyl, (C.sub.1-C.sub.6)-haloalkylsulfonyl-(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)-haloalkylsulfinyl-(C.sub.1-C.sub.6)-haloalkyl, (C.sub.1-C.sub.6)-alkylsulfonyloxy, (C.sub.1-C.sub.6)-haloalkylsulfonyloxy, (C.sub.1-C.sub.6)-alkylthiocarbonyl, (C.sub.1-C.sub.6)-haloalkylthiocarbonyl, (C.sub.1-C.sub.6)-alkylthiocarbonyloxy, (C.sub.1-C.sub.6)-haloalkylthiocarbonyloxy, (C.sub.1-C.sub.6)-alkylthio-(C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-alkylthio-(C.sub.1-C.sub.6)-alkoxy, (C.sub.1-C.sub.6)-alkylthio-(C.sub.1-C.sub.6)-alkylcarbonyl, (C.sub.1-C.sub.6)-alkylthio-(C.sub.1-C.sub.6)-alkylcarbonyloxy; (C.sub.4-C.sub.14)-arylsulfonyl, (C.sub.6-C.sub.14)-arylthio, (C.sub.6-C.sub.14)-arylsulfinyl, (C.sub.3-C.sub.8)-cycloalkylthio, (C.sub.3-C.sub.8)-alkenylthio, (C.sub.3-C.sub.8)-cycloalkenylthio, (C.sub.3-C.sub.6)-alkynylthio; and R.sup.1 and R.sup.2a may be joined to one another via a bond so as to form, together with carbon 4 (or carbon 6) and 5 of the pyrimidine and the carbonyl group in the 5 position of the pyrimidine, a 5- to 7-membered partly hydrogenated carbo- or heterocycle which may also be substituted; R.sup.3 is selected from the group consisting of hydrogen, (C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-alkoxy, (C.sub.1-C.sub.6)-alkoxy-(C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-alkoxycarbonyl and aminocarbonyl; R.sup.4 and R.sup.5 are each independently selected from the group consisting of hydrogen, (C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-haloalkyl, hydroxyl, (C.sub.1-C.sub.6)-alkoxy and (C.sub.1-C.sub.6)-haloalkoxy; or the R.sup.4 and R.sup.5 radicals together with the carbon atom to which they are bonded form a three- to seven-membered ring; and R.sup.6 and R.sup.7 are each independently selected from the group consisting of hydrogen, (C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-haloalkyl, (C.sub.1-C.sub.6)-alkoxy, (C.sub.1-C.sub.6)-haloalkoxy, (C.sub.6-C.sub.14)-aryl, (C.sub.6-C.sub.14)-aryloxy, (C.sub.6-C.sub.14)-arylcarbonyl and (C.sub.6-C.sub.14)-aryloxycarbonyl; or the R.sup.6 and R.sup.7 radicals together form a (C.sub.1-C.sub.7)-alkylene group which may contain one or more oxygen and/or sulfur atoms, where the (C.sub.1-C.sub.7)-alkylene group may be mono- or polysubstituted by halogen and the respective halogen substituents may be the same or different, and n is the serial number 0, 1 or 2 and R.sup.8, R.sup.9, R.sup.10 and R.sup.11 are each independently selected from the group consisting of hydrogen, halogen, cyano, C(O)OH, C(O)NH.sub.2, (C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-alkylcarbonyl, (C.sub.1-C.sub.6)-alkyloxycarbonyl, (C.sub.1-C.sub.6)-alkylaminocarbonyl, (C.sub.1-C.sub.6)-dialkylaminocarbonyl, (C.sub.1-C.sub.6)-haloalkyl, (C.sub.1-C.sub.6)-alkoxy, (C.sub.1-C.sub.6)-haloalkoxy, (C.sub.2-C.sub.6)-alkenyl, (C.sub.2-C.sub.6)-alkynyl, (C.sub.2-C.sub.6)-haloalkynyl, (C.sub.2-C.sub.6)-alkynylcarbonyl, (C.sub.2-C.sub.6)-haloalkynylcarbonyl, (C.sub.2-C.sub.6)-alkynyloxy, (C.sub.2-C.sub.6)-haloalkynyloxy, (C.sub.2-C.sub.6)-alkynyloxycarbonyl and (C.sub.2-C.sub.6)-haloalkynyloxycarbonyl and nitro; X is a bond (if n=1 or n=2), CH.sub.2, O, S, carbonyl, NH, CR.sup.12R.sup.13 and NR.sup.14 or CH.sub.2O, CH.sub.2S, where the carbon atom in the two latter groups is bonded to the aromatic moiety and the heteroatom O or S to the partly hydrogenated amine moiety; and R.sup.12 and R.sup.13 are each independently selected from the group consisting of hydrogen, (C.sub.1-C.sub.6)-alkyl and (C.sub.1-C.sub.6)-haloalkyl; and R.sup.14 is selected from the group consisting of hydrogen, (C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-haloalkyl.

2. A compound of formula (I) and/or salt as claimed in claim 1, wherein the compound 1-[2-[(7-methoxy-2,2-dimethylchroman-4-yl)amino]-4-methylpyrimidin-5-yl)ethanone having the empirical formula C.sub.19H.sub.23N.sub.3O.sub.3 is excluded.

3. A compound of formula (I) and/or salt as claimed in claim 1, wherein R.sup.1 is selected from the group consisting of (C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-haloalkyl, (C.sub.1-C.sub.6)-alkoxy, (C.sub.1-C.sub.6)-alkoxy-(C.sub.1-C.sub.6)-alkyl, (C.sub.3-C.sub.8)-cycloalkyl, (C.sub.3-C.sub.8)-cycloalkyl-(C.sub.1-C.sub.6)-alkyl or (C.sub.3-C.sub.8)-cycloalkyl-(C.sub.1-C.sub.6)-haloalkyl, where the cycloalkyl radical in each case is unsubstituted or substituted by (C.sub.1-C.sub.6)-alkyl and/or halogen.

4. A compound of formula (I) and/or salt as claimed in claim 1, wherein the R.sup.2a and R.sup.2b radicals are each independently selected from the group consisting of hydrogen, (C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-haloalkyl, (C.sub.1-C.sub.6)-alkoxy, (C.sub.1-C.sub.6)-alkoxy-(C.sub.1-C.sub.6)-alkyl, (C.sub.3-C.sub.8)-cycloalkyl, (C.sub.3-C.sub.8)-cycloalkyl-(C.sub.1-C.sub.6)-alkyl or (C.sub.3-C.sub.8)-cycloalkyl-(C.sub.1-C.sub.6)-haloalkyl, where the cycloalkyl radical in each case is unsubstituted or substituted by (C.sub.1-C.sub.6)-alkyl and/or halogen.

5. A compound of formula (I) and/or salt as claimed in claim 1, wherein the radical R.sup.3 is selected from the group consisting of hydrogen, (C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-alkoxy, (C.sub.1-C.sub.6)-alkoxy-(C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-alkoxycarbonyl and aminocarbonyl.

6. A compound of formula (I) and/or salt as claimed in claim 1, wherein the R.sup.4 and R.sup.5 radicals are each independently selected from the group consisting of hydrogen, hydroxyl, (C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-alkylphenyl and (C.sub.1-C.sub.6)-alkoxy.

7. A compound of formula (I) and/or salt as claimed in, wherein the R.sup.6 and R.sup.7 radicals are each independently selected from the group consisting of hydrogen, (C.sub.1-C.sub.6)-alkyl and (C.sub.6-C.sub.14)-aryl.

8. A compound of formula (I) and/or salt as claimed in claim 1, wherein the R.sup.8 radical is selected from the group consisting of hydrogen, halogen, (C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-alkoxy and (C.sub.6-C.sub.14)-aryl.

9. A compound of formula (I) and/or salt as claimed in claim 1, wherein the R.sup.9 radical is selected from the group consisting of hydrogen, halogen, (C.sub.1-C.sub.6)-alkyl and (C.sub.1-C.sub.6)-alkoxy.

10. A compound of formula (I) and/or salt as claimed in claim 1, wherein the R.sup.10 radical is selected from the group consisting of hydrogen, halogen, cyano, aminocarbonyl, hydroxycarbonyl, (C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-haloalkyl, (C.sub.1-C.sub.6)-alkoxy, (C.sub.2-C.sub.6)-alkenyl, (C.sub.2-C.sub.6)-alkynyl, (C.sub.1-C.sub.6)-alkyl-(C.sub.2-C.sub.6)-alkynyl, hydroxy-(C.sub.1-C.sub.6)-alkyl-(C.sub.2-C.sub.6)-alkynyl, (C.sub.1-C.sub.6)-alkoxy-(C.sub.2-C.sub.6)-alkynyl and aryl-(C.sub.2-C.sub.6)-alkynyl.

11. A compound of formula (I) and/or salt as claimed in claim 1, wherein the R.sup.11 radical is selected from the group consisting of hydrogen and (C.sub.1-C.sub.6)-alkyl.

12. A compound of formula (I) and/or salt as claimed in claim 1, wherein the X radical is selected from the group consisting of O, S, carbonyl, CH.sub.2, NH, N(C.sub.1-C.sub.6)alkyl, CH(C.sub.1-C.sub.6)alkyl, di-(C.sub.1-C.sub.6)-alkylalkylene, O(C.sub.1-C.sub.7)alkylene, S(C.sub.1-C.sub.7)alkylene, (C.sub.1-C.sub.6)alkylamino, or in which X is a chemical bond.

13. A compound of formula (I) and/or salt as claimed in claim 1, wherein the R.sup.1 and R.sup.2a radicals together with carbons 4 and 5 of the pyrimidine and the carbonyl group in the 5 position of the pyrimidine give a 5- to 7-membered partly hydrogenated carbo- or heterocycle in which the heteroatoms are selected from the group consisting of oxygen and sulfur, where a sulfoxide group or a sulfonyl group may be present in place of the sulfur, and the carbo- or heterocycle is unsubstituted or at least monosubstituted and where the substituents are selected from the group consisting of (C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-haloalkyl, aryl, especially phenyl (C.sub.6H.sub.5) which is unsubstituted or at least monosubstituted by fluorine, chlorine, bromine or iodine, and (C.sub.1-C.sub.6)-cycloalkyl.

14. A compound of formula (I) and/or salt as claimed in claim 1, wherein the R.sup.9 and R.sup.10 radicals are joined by a OCH.sub.2O group to form a ring.

15. A compound of formula (I) ##STR00016## And/or salt as claimed in claim 1, wherein the chiral carbon atom indicated by (*) has (R) configuration.

16. A compound of formula (I) ##STR00017## And/or salt as claimed in claim 1, wherein the chiral carbon atom indicated by (*) has (R) configuration and the chiral carbon atom indicated by (**) has (S) configuration.

17. A process for preparing one or more compounds of formula (I) and/or one or more agrochemically acceptable salts thereof and/or one or more agrochemically acceptable quaternized nitrogen derivatives thereof ##STR00018## in which the R.sup.1 to R.sup.11 and X radicals are R.sup.1 is selected from the group consisting of (C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-haloalkyl, (C.sub.1-C.sub.6)-alkylcarbonyl-(C.sub.1-C.sub.4)-alkyl; (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.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: tri-(C.sub.1-C.sub.6)-alkylsilyl-(C.sub.2-C.sub.6)-alkynyl, di-(C.sub.1-C.sub.6)-alkylsilyl-(C.sub.2-C.sub.6)-alkynyl, mono-(C.sub.1-C.sub.6)-alkylsilyl-(C.sub.2-C.sub.6)-alkynyl; phenylsilyl-(C.sub.2-C.sub.6)-alkynyl; (C.sub.6-C.sub.14)-aryl which may be substituted in the aryl moiety in each case by halogen, (C.sub.1-C.sub.6)-alkyl and/or (C.sub.1-C.sub.6)-haloalkyl; (C.sub.6-C.sub.14)-aryl-(C.sub.1-C.sub.6)-alkyl; aminocarbonyl-(C.sub.1-C.sub.6)-alkyl; (C.sub.1-C.sub.6)-alkoxy-(C.sub.1-C.sub.6)-alkyl, (C.sub.3-C.sub.8)-cycloalkyl which may optionally be substituted in the cycloalkyl radical by (C.sub.1-C.sub.6)-alkyl and/or halogen: (C.sub.3-C.sub.8)-cycloalkyl-(C.sub.1-C.sub.6)-alkyl, (C.sub.3-C.sub.8)-cycloalkyl-(C.sub.1-C.sub.6)-haloalkyl (C.sub.3-C.sub.8)-cycloalkenyl, (C.sub.3-C.sub.8)-cycloalkenyl-(C.sub.1-C.sub.6)-alkyl, (C.sub.3-C.sub.8)-cycloalkenyl-(C.sub.1-C.sub.6)-haloalkyl, hydroxy-(C.sub.1-C.sub.6)-alkyl, cyano-(C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-alkylsulfonyl-(C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-alkylthio-(C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-alkylsulfinyl-(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)-haloalkylthio-(C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-haloalkyl sulfinyl-(C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-alkylsulfonyl-(C.sub.1-C.sub.6)-haloalkyl, (C.sub.1-C.sub.6)-alkylthio-(C.sub.1-C.sub.6)-haloalkyl, (C.sub.1-C.sub.6)-alkylsulfinyl-(C.sub.1-C.sub.6)-haloalkyl, (C.sub.1-C.sub.6)-haloalkylsulfonyl-(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)-haloalkylsulfinyl-(C.sub.1-C.sub.6)-haloalkyl, and R.sup.2 and R.sup.2b are each independently selected from the group consisting of hydrogen, halogen, hydroxyl, cyano, nitro, C(O)OH, C(O)NH.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.1-C.sub.6)-haloalkylcarbonyl, (C.sub.1-C.sub.6)-alkylcarbonyloxy, (C.sub.1-C.sub.6)-haloalkylcarbonyloxy, (C.sub.1-C.sub.6)-alkylcarbonyl-(C.sub.1-C.sub.4)-alkyl, (C.sub.1-C.sub.6)-alkoxy, (C.sub.1-C.sub.6)-haloalkoxy, (C.sub.1-C.sub.6)-alkoxycarbonyl, (C.sub.1-C.sub.6)-haloalkoxycarbonyl, (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.2-C.sub.6)-alkenyl, (C.sub.2-C.sub.6)-haloalkenyl, (C.sub.2-C.sub.6)-alkenylcarbonyl, (C.sub.2-C.sub.6)-haloalkenylcarbonyl, (C.sub.2-C.sub.6)-alkenyloxy, (C.sub.2-C.sub.6)-haloalkenyloxy, (C.sub.2-C.sub.6)-alkenyloxycarbonyl, (C.sub.2-C.sub.6)-haloalkenyloxycarbonyl; (C.sub.2-C.sub.6)-alkynyl, (C.sub.2-C.sub.6)-haloalkynyl, (C.sub.2-C.sub.6)-alkynylcarbonyl, (C.sub.2-C.sub.6)-haloalkynylcarbonyl, (C.sub.2-C.sub.6)-alkynyloxy, (C.sub.2-C.sub.6)-haloalkynyloxy, (C.sub.2-C.sub.6)-alkynyloxycarbonyl, (C.sub.2-C.sub.6)-haloalkynyloxycarbonyl; tri-(C.sub.1-C.sub.6)-alkylsilyl-(C.sub.2-C.sub.6)-alkynyl, di-(C.sub.1-C.sub.6)-alkylsilyl-(C.sub.2-C.sub.6)-alkynyl, mono-(C.sub.1-C.sub.6)-alkylsilyl-(C.sub.2-C.sub.6)-alkynyl; phenylsilyl-(C.sub.2-C.sub.6)-alkynyl; (C.sub.6-C.sub.14)-aryl, (C.sub.6-C.sub.14)-aryloxy, (C.sub.6-C.sub.14)-arylcarbonyl and (C.sub.6-C.sub.14)-aryloxycarbonyl, each of which may be substituted in the aryl moiety by halogen, (C.sub.1-C.sub.6)-alkyl and/or (C.sub.1-C.sub.6)-haloalkyl; (C.sub.6-C.sub.14)-aryl-(C.sub.1-C.sub.6)-alkyl, (C.sub.6-C.sub.14)-aryl-(C.sub.1-C.sub.6)-alkoxy, (C.sub.6-C.sub.14)-aryl-(C.sub.1-C.sub.6)-alkylcarbonyl, (C.sub.6-C.sub.14)-aryl-(C.sub.1-C.sub.6)-alkylcarbonyloxy, (C.sub.6-C.sub.14)-aryl-(C.sub.1-C.sub.6)-alkoxycarbonyl, (C.sub.6-C.sub.14)-aryl-(C.sub.1-C.sub.6)-alkoxycarbonyloxy; aminocarbonyl-(C.sub.1-C.sub.6)-alkyl, di-(C.sub.1-C.sub.6)-alkylaminocarbonyl-(C.sub.1-C.sub.6)-alkyl, N((C.sub.1-C.sub.6)-haloalkanoyl)-aminocarbonyl, mono-((C.sub.6-C.sub.14)-aryl)-aminocarbonyl, di-((C.sub.6-C.sub.14)-aryl)-aminocarbonyl; (C.sub.1-C.sub.6)-alkoxy-(C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-alkoxy-(C.sub.1-C.sub.6)-alkoxy, (C.sub.1-C.sub.6)-alkoxycarbonyl-(C.sub.1-C.sub.6)-alkoxy; (C.sub.3-C.sub.8)-cycloalkyl which may optionally be substituted in the cycloalkyl radical by (C.sub.1-C.sub.6)-alkyl and/or halogen: (C.sub.3-C.sub.8)-cycloalkoxy, (C.sub.3-C.sub.8)-cycloalkyl-(C.sub.1-C.sub.6)-alkyl, (C.sub.3-C.sub.8)-cycloalkyl-(C.sub.1-C.sub.6)-haloalkyl, (C.sub.3-C.sub.8)-cycloalkyl-(C.sub.1-C.sub.6)-alkoxy, (C.sub.3-C.sub.8)-cycloalkyl-(C.sub.1-C.sub.6)-haloalkoxy, (C.sub.3-C.sub.8)-cycloalkylcarbonyl, (C.sub.3-C.sub.8)-cycloalkoxycarbonyl, (C.sub.3-C.sub.8)-cycloalkyl-(C.sub.1-C.sub.6)-alkylcarbonyl, (C.sub.3-C.sub.8)-cycloalkyl-(C.sub.1-C.sub.6)-haloalkylcarbonyl, (C.sub.3-C.sub.8)-cycloalkyl-(C.sub.1-C.sub.6)-alkoxycarbonyl, (C.sub.3-C.sub.8)-cycloalkyl-(C.sub.1-C.sub.6)-haloalkoxycarbonyl, (C.sub.3-C.sub.8)-cycloalkylcarbonyloxy, (C.sub.3-C.sub.8)-cycloalkoxycarbonyloxy, (C.sub.3-C.sub.8)-cycloalkyl-(C.sub.1-C.sub.6)-alkylcarbonyloxy, (C.sub.3-C.sub.8)-cycloalkyl-(C.sub.1-C.sub.6)-haloalkylcarbonyloxy, (C.sub.3-C.sub.8) cycloalkyl-(C.sub.1-C.sub.6)-alkoxycarbonyloxy, (C.sub.3-C.sub.8)-cycloalkyl-(C.sub.1-C.sub.6)-haloalkoxycarbonyloxy, (C.sub.3-C.sub.8)-cycloalkenyl, (C.sub.3-C.sub.8)-cycloalkenyloxy, (C.sub.3-C.sub.8)-cycloalkenyl-(C.sub.1-C.sub.6)-alkyl, (C.sub.3-C.sub.8)-cycloalkenyl-(C.sub.1-C.sub.6)-haloalkyl, (C.sub.3-C.sub.8)-cycloalkenyl-(C.sub.1-C.sub.6)-alkoxy, (C.sub.3-C.sub.8)-cycloalkenyl-(C.sub.1-C.sub.6)-haloalkoxy, (C.sub.3-C.sub.8)-cycloalkenylcarbonyl, (C.sub.3-C.sub.8)-cycloalkenyloxycarbonyl, (C.sub.3-C.sub.8)-cycloalkenyl-(C.sub.1-C.sub.6)-alkylcarbonyl, (C.sub.3-C.sub.8)-cycloalkenyl-(C.sub.1-C.sub.6)-haloalkylcarbonyl, (C.sub.3-C.sub.8)-cycloalkenyl-(C.sub.1-C.sub.6)-alkoxycarbonyl, (C.sub.3-C.sub.8)-cycloalkenyl-(C.sub.1-C.sub.6)-haloalkoxycarbonyl, (C.sub.3-C.sub.8)-cycloalkenylcarbonyloxy, (C.sub.3-C.sub.8)-cycloalkenyloxycarbonyloxy, (C.sub.3-C.sub.8)-cycloalkenyl-(C.sub.1-C.sub.6)-alkylcarbonyloxy, (C.sub.3-C.sub.8)-cycloalkenyl-(C.sub.1-C.sub.6)-haloalkylcarbonyloxy, (C.sub.3-C.sub.8)-cycloalkenyl-(C.sub.1-C.sub.6)-alkoxycarbonyloxy, (C.sub.3-C.sub.8) cycloalkenyl-(C.sub.1-C.sub.6)-haloalkoxycarbonyloxy; hydroxy-(C.sub.1-C.sub.6)-alkyl, hydroxy-(C.sub.1-C.sub.6)-alkoxy, cyano-(C.sub.1-C.sub.6)-alkoxy, cyano-(C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-alkylsulfonyl, (C.sub.1-C.sub.6)-alkylthio, (C.sub.1-C.sub.6)-alkylsulfinyl, (C.sub.1-C.sub.6)-haloalkyl sulfonyl, (C.sub.1-C.sub.6)-haloalkylthio, (C.sub.1-C.sub.6)-haloalkylsulfinyl, (C.sub.1-C.sub.6)-alkylsulfonyl-(C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-alkylthio-(C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-alkylsulfinyl-(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)-haloalkylthio-(C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-haloalkylsulfinyl-(C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-alkylsulfonyl-(C.sub.1-C.sub.6)-haloalkyl, (C.sub.1-C.sub.6)-alkylthio-(C.sub.1-C.sub.6)-haloalkyl, (C.sub.1-C.sub.6)-alkylsulfinyl-(C.sub.1-C.sub.6)-haloalkyl, (C.sub.1-C.sub.6)-haloalkylsulfonyl-(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)-haloalkylsulfinyl-(C.sub.1-C.sub.6)-haloalkyl, (C.sub.1-C.sub.6)-alkylsulfonyloxy, (C.sub.1-C.sub.6)-haloalkylsulfonyloxy, (C.sub.1-C.sub.6)-alkylthiocarbonyl, (C.sub.1-C.sub.6)-haloalkylthiocarbonyl, (C.sub.1-C.sub.6)-alkylthiocarbonyloxy, (C.sub.1-C.sub.6)-haloalkylthiocarbonyloxy, (C.sub.1-C.sub.6)-alkylthio-(C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-alkylthio-(C.sub.1-C.sub.6)-alkoxy, (C.sub.1-C.sub.6)-alkylthio-(C.sub.1-C.sub.6)-alkylcarbonyl, (C.sub.1-C.sub.6)-alkylthio-(C.sub.1-C.sub.6)-alkylcarbonyloxy: (C.sub.4-C.sub.14)-arylsulfonyl, (C.sub.6-C.sub.14)-arylthio, (C.sub.6-C.sub.14)-arylsulfinyl, (C.sub.3-C.sub.8)-cycloalkylthio, (C.sub.3-C.sub.8)-alkenylthio, (C.sub.3-C.sub.8)-cycloalkenylthio, (C.sub.3-C.sub.6)-alkynylthio, and R.sup.1 and R.sup.2a may be joined to one another via a bond so as to form, together with carbon 4 (or carbon 6) and 5 of the pyrimidine and the carbonyl group in the 5 position of the pyrimidine, a 5- to 7-membered partly hydrogenated carbo- or heterocycle which may also be substituted; R.sup.3 is selected from the group consisting of hydrogen, (C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-alkoxy, (C.sub.1-C.sub.6)-alkoxy-(C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-alkoxycarbonyl and aminocarbonyl; R.sup.4 and R.sup.5 are each independently selected from the group consisting of hydrogen, (C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-haloalkyl, hydroxyl, (C.sub.1-C.sub.6)-alkoxy and (C.sub.1-C.sub.6)-haloalkoxy; or the R.sup.4 and R.sup.5 radicals together with the carbon atom to which they are bonded form a three- to seven-membered ring; and R.sup.6 and R.sup.7 are each independently selected from the group consisting of hydrogen, (C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-haloalkyl, (C.sub.1-C.sub.6)-alkoxy, (C.sub.1-C.sub.6)-haloalkoxy, (C.sub.6-C.sub.14)-aryl, (C.sub.6-C.sub.14)-aryloxy, (C.sub.6-C.sub.14)-arylcarbonyl and (C.sub.6-C.sub.14)-aryloxycarbonyl; or the R.sup.6 and R.sup.7 radicals together form a (C.sub.1-C.sub.7)-alkylene group which may contain one or more oxygen and/or sulfur atoms, where the (C.sub.1-C.sub.7)-alkylene group may be mono- or polysubstituted by halogen and the respective halogen substituents may be the same or different, and n is the serial number 0, 1 or 2 and R.sup.8, R.sup.9, R.sup.10 and R.sup.11 are each independently selected from the group consisting of hydrogen, halogen, cyano, C(O)OH, C(O)NH.sub.2, (C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-alkylcarbonyl, (C.sub.1-C.sub.6)-alkyloxycarbonyl, (C.sub.1-C.sub.6)-alkylaminocarbonyl, (C.sub.1-C.sub.6)-dialkylaminocarbonyl, (C.sub.1-C.sub.6)-haloalkyl, (C.sub.1-C.sub.6)-alkoxy, (C.sub.1-C.sub.6)-haloalkoxy, (C.sub.2-C.sub.6)-alkenyl, (C.sub.2-C.sub.6)-alkynyl, (C.sub.2-C.sub.6)-haloalkynyl, (C.sub.2-C.sub.6)-alkynylcarbonyl, (C.sub.2-C.sub.6)-haloalkynylcarbonyl, (C.sub.2-C.sub.6)-alkynyloxy, (C.sub.2-C.sub.6)-haloalkynyloxy, (C.sub.2-C.sub.6)-alkynyloxycarbonyl and (C.sub.2-C.sub.6)-haloalkynyloxycarbonyl and nitro; X is a bond (if n=1 or n=2), CH.sub.2, O, S, carbonyl, NH, CR.sup.12R.sup.13 and NR.sup.14 or CH.sub.2O, CH.sub.2S, where the carbon atom in the two latter groups is bonded to the aromatic moiety and the heteroatom O or S to the partly hydrogenated amine moiety; and R.sup.12 and R.sup.13 are each independently selected from the group consisting of hydrogen, (C.sub.1-C.sub.6)-alkyl and (C.sub.1-C.sub.6)-haloalkyl; and R.sup.14 is selected from the group consisting of hydrogen, (C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-haloalkyl Said process comprising reacting a compound of formula (II) ##STR00019## wherein Z.sup.1 is an exchangeable radical or a leaving group, with an amine of formula (III) or with an acid addition salt of an amine of formula (III) ##STR00020##

18. The process as claimed in claim 17, wherein the exchangeable radical or the leaving group Z.sup.1 is fluorine, chlorine, bromine, iodine, a (C.sub.1-C.sub.4)-alkylsulfanyl or a (C.sub.1-C.sub.4)-alkylsulfinyl or a (C.sub.1-C.sub.4)-alkylsulfonyl, an unsubstituted or substituted phenyl-(C.sub.1-C.sub.4)-alkylsulfonyl or a (C.sub.1-C.sub.4)-alkylphenylsulfonyl.

19. A process for preparing compounds of formula (I) and/or agrochemically acceptable salts thereof and/or agrochemically acceptable quaternized nitrogen derivatives thereof ##STR00021## in which the R.sup.1 to R.sup.11 and X radicals are R.sup.1 is selected from the group consisting of (C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-haloalkyl, (C.sub.1-C.sub.6)-alkylcarbonyl-(C.sub.1-C.sub.4)-alkyl; (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.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: tri-(C.sub.1-C.sub.6)-alkylsilyl-(C.sub.2-C.sub.6)-alkynyl, di-(C.sub.1-C.sub.6)-alkylsilyl-(C.sub.2-C.sub.6)-alkynyl, mono-(C.sub.1-C.sub.6)-alkylsilyl-(C.sub.2-C.sub.6)-alkynyl; phenylsilyl-(C.sub.2-C.sub.6)-alkynyl; (C.sub.6-C.sub.14)-aryl which may be substituted in the aryl moiety in each case by halogen, (C.sub.1-C.sub.6)-alkyl and/or (C.sub.1-C.sub.6)-haloalkyl; (C.sub.6-C.sub.14)-aryl-(C.sub.1-C.sub.6)-alkyl; aminocarbonyl-(C.sub.1-C.sub.6)-alkyl; (C.sub.1-C.sub.6)-alkoxy-(C.sub.1-C.sub.6)-alkyl, (C.sub.3-C.sub.8)-cycloalkyl which may optionally be substituted in the cycloalkyl radical by (C.sub.1-C.sub.6)-alkyl and/or halogen: (C.sub.3-C.sub.8)-cycloalkyl-(C.sub.1-C.sub.6)-alkyl, (C.sub.3-C.sub.8)-cycloalkyl-(C.sub.1-C.sub.6)-haloalkyl (C.sub.3-C.sub.8)-cycloalkenyl, (C.sub.3-C.sub.8)-cycloalkenyl-(C.sub.1-C.sub.6)-alkyl, (C.sub.3-C.sub.8)-cycloalkenyl-(C.sub.1-C.sub.6)-haloalkyl, hydroxy-(C.sub.1-C.sub.6)-alkyl, cyano-(C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-alkylsulfonyl-(C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-alkylthio-(C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-alkylsulfinyl-(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)-haloalkylthio-(C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-haloalkyl sulfinyl-(C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-alkylsulfonyl-(C.sub.1-C.sub.6)-haloalkyl, (C.sub.1-C.sub.6)-alkylthio-(C.sub.1-C.sub.6)-haloalkyl, (C.sub.1-C.sub.6)-alkylsulfinyl-(C.sub.1-C.sub.6)-haloalkyl, (C.sub.1-C.sub.6)-haloalkylsulfonyl-(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)-haloalkylsulfinyl-(C.sub.1-C.sub.6)-haloalkyl, and R.sup.2 and R.sup.2b are each independently selected from the group consisting of hydrogen, halogen, hydroxyl, cyano, nitro, C(O)OH, C(O)NH.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.1-C.sub.6)-haloalkylcarbonyl, (C.sub.1-C.sub.6)-alkylcarbonyloxy, (C.sub.1-C.sub.6)-haloalkylcarbonyloxy, (C.sub.1-C.sub.6)-alkylcarbonyl-(C.sub.1-C.sub.4)-alkyl, (C.sub.1-C.sub.6)-alkoxy, (C.sub.1-C.sub.6)-haloalkoxy, (C.sub.1-C.sub.6)-alkoxycarbonyl, (C.sub.1-C.sub.6)-haloalkoxycarbonyl, (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.2-C.sub.6)-alkenyl, (C.sub.2-C.sub.6)-haloalkenyl, (C.sub.2-C.sub.6)-alkenylcarbonyl, (C.sub.2-C.sub.6)-haloalkenylcarbonyl, (C.sub.2-C.sub.6)-alkenyloxy, (C.sub.2-C.sub.6)-haloalkenyloxy, (C.sub.2-C.sub.6)-alkenyloxycarbonyl, (C.sub.2-C.sub.6)-haloalkenyloxycarbonyl; (C.sub.2-C.sub.6)-alkynyl, (C.sub.2-C.sub.6)-haloalkynyl, (C.sub.2-C.sub.6)-alkynylcarbonyl, (C.sub.2-C.sub.6)-haloalkynylcarbonyl, (C.sub.2-C.sub.6)-alkynyloxy, (C.sub.2-C.sub.6)-haloalkynyloxy, (C.sub.2-C.sub.6)-alkynyloxycarbonyl, (C.sub.2-C.sub.6)-haloalkynyloxycarbonyl; tri-(C.sub.1-C.sub.6)-alkylsilyl-(C.sub.2-C.sub.6)-alkynyl, di-(C.sub.1-C.sub.6)-alkylsilyl-(C.sub.2-C.sub.6)-alkynyl, mono-(C.sub.1-C.sub.6)-alkylsilyl-(C.sub.2-C.sub.6)-alkynyl; phenylsilyl-(C.sub.2-C.sub.6)-alkynyl; (C.sub.6-C.sub.14)-aryl, (C.sub.6-C.sub.14)-aryloxy, (C.sub.6-C.sub.14)-arylcarbonyl and (C.sub.6-C.sub.14)-aryloxycarbonyl, each of which may be substituted in the aryl moiety by halogen, (C.sub.1-C.sub.6)-alkyl and/or (C.sub.1-C.sub.6)-haloalkyl; (C.sub.6-C.sub.14)-aryl-(C.sub.1-C.sub.6)-alkyl, (C.sub.6-C.sub.14)-aryl-(C.sub.1-C.sub.6)-alkoxy, (C.sub.6-C.sub.14)-aryl-(C.sub.1-C.sub.6)-alkylcarbonyl, (C.sub.6-C.sub.14)-aryl-(C.sub.1-C.sub.6)-alkylcarbonyloxy, (C.sub.6-C.sub.14)-aryl-(C.sub.1-C.sub.6)-alkoxycarbonyl, (C.sub.6-C.sub.14)-aryl-(C.sub.1-C.sub.6)-alkoxycarbonyloxy; aminocarbonyl-(C.sub.1-C.sub.6)-alkyl, di-(C.sub.1-C.sub.6)-alkylaminocarbonyl-(C.sub.1-C.sub.6)-alkyl, N((C.sub.1-C.sub.6)-haloalkanoyl)-aminocarbonyl, mono-((C.sub.6-C.sub.14)-aryl)-aminocarbonyl, di-((C.sub.6-C.sub.14)-aryl)-aminocarbonyl; (C.sub.1-C.sub.6)-alkoxy-(C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-alkoxy-(C.sub.1-C.sub.6)-alkoxy, (C.sub.1-C.sub.6)-alkoxycarbonyl-(C.sub.1-C.sub.6)-alkoxy; (C.sub.3-C.sub.8)-cycloalkyl which may optionally be substituted in the cycloalkyl radical by (C.sub.1-C.sub.6)-alkyl and/or halogen: (C.sub.3-C.sub.8)-cycloalkoxy, (C.sub.3-C.sub.8)-cycloalkyl-(C.sub.1-C.sub.6)-alkyl, (C.sub.3-C.sub.8)-cycloalkyl-(C.sub.1-C.sub.6)-haloalkyl, (C.sub.3-C.sub.8)-cycloalkyl-(C.sub.1-C.sub.6)-alkoxy, (C.sub.3-C.sub.8)-cycloalkyl-(C.sub.1-C.sub.6)-haloalkoxy, (C.sub.3-C.sub.8)-cycloalkylcarbonyl, (C.sub.3-C.sub.8)-cycloalkoxycarbonyl, (C.sub.3-C.sub.8)-cycloalkyl-(C.sub.1-C.sub.6)-alkylcarbonyl, (C.sub.3-C.sub.8)-cycloalkyl-(C.sub.1-C.sub.6)-haloalkylcarbonyl, (C.sub.3-C.sub.8)-cycloalkyl-(C.sub.1-C.sub.6)-alkoxycarbonyl, (C.sub.3-C.sub.8)-cycloalkyl-(C.sub.1-C.sub.6)-haloalkoxycarbonyl, (C.sub.3-C.sub.8)-cycloalkylcarbonyloxy, (C.sub.3-C.sub.8)-cycloalkoxycarbonyloxy, (C.sub.3-C.sub.8)-cycloalkyl-(C.sub.1-C.sub.6)-alkylcarbonyloxy, (C.sub.3-C.sub.8)-cycloalkyl-(C.sub.1-C.sub.6)-haloalkylcarbonyloxy, (C.sub.3-C.sub.8) cycloalkyl-(C.sub.1-C.sub.6)-alkoxycarbonyloxy, (C.sub.3-C.sub.8)-cycloalkyl-(C.sub.1-C.sub.6)-haloalkoxycarbonyloxy, (C.sub.3-C.sub.8)-cycloalkenyl, (C.sub.3-C.sub.8)-cycloalkenyloxy, (C.sub.3-C.sub.8)-cycloalkenyl-(C.sub.1-C.sub.6)-alkyl, (C.sub.3-C.sub.8)-cycloalkenyl-(C.sub.1-C.sub.6)-haloalkyl, (C.sub.3-C.sub.8)-cycloalkenyl-(C.sub.1-C.sub.6)-alkoxy, (C.sub.3-C.sub.8)-cycloalkenyl-(C.sub.1-C.sub.6)-haloalkoxy, (C.sub.3-C.sub.8)-cycloalkenylcarbonyl, (C.sub.3-C.sub.8)-cycloalkenyloxycarbonyl, (C.sub.3-C.sub.8)-cycloalkenyl-(C.sub.1-C.sub.6)-alkylcarbonyl, (C.sub.3-C.sub.8)-cycloalkenyl-(C.sub.1-C.sub.6)-haloalkylcarbonyl, (C.sub.3-C.sub.8)-cycloalkenyl-(C.sub.1-C.sub.6)-alkoxycarbonyl, (C.sub.3-C.sub.8)-cycloalkenyl-(C.sub.1-C.sub.6)-haloalkoxycarbonyl, (C.sub.3-C.sub.8)-cycloalkenylcarbonyloxy, (C.sub.3-C.sub.8)-cycloalkenyloxycarbonyloxy, (C.sub.3-C.sub.8)-cycloalkenyl-(C.sub.1-C.sub.6)-alkylcarbonyloxy, (C.sub.3-C.sub.8)-cycloalkenyl-(C.sub.1-C.sub.6)-haloalkylcarbonyloxy, (C.sub.3-C.sub.8)-cycloalkenyl-(C.sub.1-C.sub.6)-alkoxycarbonyloxy, (C.sub.3-C.sub.8) cycloalkenyl-(C.sub.1-C.sub.6)-haloalkoxycarbonyloxy; hydroxy-(C.sub.1-C.sub.6)-alkyl, hydroxy-(C.sub.1-C.sub.6)-alkoxy, cyano-(C.sub.1-C.sub.6)-alkoxy, cyano-(C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-alkylsulfonyl, (C.sub.1-C.sub.6)-alkylthio, (C.sub.1-C.sub.6)-alkylsulfinyl, (C.sub.1-C.sub.6)-haloalkyl sulfonyl, (C.sub.1-C.sub.6)-haloalkylthio, (C.sub.1-C.sub.6)-haloalkylsulfinyl, (C.sub.1-C.sub.6)-alkylsulfonyl-(C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-alkylthio-(C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-alkylsulfinyl-(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)-haloalkylthio-(C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-haloalkylsulfinyl-(C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-alkylsulfonyl-(C.sub.1-C.sub.6)-haloalkyl, (C.sub.1-C.sub.6)-alkylthio-(C.sub.1-C.sub.6)-haloalkyl, (C.sub.1-C.sub.6)-alkylsulfinyl-(C.sub.1-C.sub.6)-haloalkyl, (C.sub.1-C.sub.6)-haloalkylsulfonyl-(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)-haloalkylsulfinyl-(C.sub.1-C.sub.6)-haloalkyl, (C.sub.1-C.sub.6)-alkylsulfonyloxy, (C.sub.1-C.sub.6)-haloalkylsulfonyloxy, (C.sub.1-C.sub.6)-alkyithiocarbonyl, (C.sub.1-C.sub.6)-haloalkylthiocarbonyl, (C.sub.1-C.sub.6)-alkylthiocarbonyloxy, (C.sub.1-C.sub.6)-haloalkylthiocarbonyloxy, (C.sub.1-C.sub.6)-alkylthio-(C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-alkylthio-(C.sub.1-C.sub.6)-alkoxy, (C.sub.1-C.sub.6)-alkylthio-(C.sub.1-C.sub.6)-alkylcarbonyl, (C.sub.1-C.sub.6)-alkylthio-(C.sub.1-C.sub.6)-alkylcarbonyloxy: (C.sub.4-C.sub.14)-arylsulfonyl, (C.sub.6-C.sub.14)-arylthio, (C.sub.6-C.sub.14)-arylsulfinyl, (C.sub.3-C.sub.8)-cycloalkylthio, (C.sub.3-C.sub.8)-alkenylthio, (C.sub.3-C.sub.8)-cycloalkenylthio, (C.sub.3-C.sub.6)-alkynylthio, and R.sup.1 and R.sup.2a may be joined to one another via a bond so as to form, together with carbon 4 (or carbon 6) and 5 of the pyrimidine and the carbonyl group in the 5 position of the pyrimidine, a 5- to 7-membered partly hydrogenated carbo- or heterocycle which may also be substituted; R.sup.3 is selected from the group consisting of hydrogen, (C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-alkoxy, (C.sub.1-C.sub.6)-alkoxy-(C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-alkoxycarbonyl and aminocarbonyl; R.sup.4 and R.sup.5 are each independently selected from the group consisting of hydrogen, (C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-haloalkyl, hydroxyl, (C.sub.1-C.sub.6)-alkoxy and (C.sub.1-C.sub.6)-haloalkoxy; or the R.sup.4 and R.sup.5 radicals together with the carbon atom to which they are bonded form a three- to seven-membered ring; and R.sup.6 and R.sup.7 are each independently selected from the group consisting of hydrogen, (C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-haloalkyl, (C.sub.1-C.sub.6)-alkoxy, (C.sub.1-C.sub.6)-haloalkoxy, (C.sub.6-C.sub.14)-aryl, (C.sub.6-C.sub.14)-aryloxy, (C.sub.6-C.sub.14)-arylcarbonyl and (C.sub.6-C.sub.14)-aryloxycarbonyl; or the R.sup.6 and R.sup.7 radicals together form a (C.sub.1-C.sub.7)-alkylene group which may contain one or more oxygen and/or sulfur atoms, where the (C.sub.1-C.sub.7)-alkylene group may be mono- or polysubstituted by halogen and the respective halogen substituents may be the same or different, and n is the serial number 0, 1 or 2 and R.sup.8, R.sup.9, R.sup.10 and R.sup.11 are each independently selected from the group consisting of hydrogen, halogen, cyano, C(O)OH, C(O)NH.sub.2, (C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-alkylcarbonyl, (C.sub.1-C.sub.6)-alkyloxycarbonyl, (C.sub.1-C.sub.6)-alkylaminocarbonyl, (C.sub.1-C.sub.6)-dialkylaminocarbonyl, (C.sub.1-C.sub.6)-haloalkyl, (C.sub.1-C.sub.6)-alkoxy, (C.sub.1-C.sub.6)-haloalkoxy, (C.sub.2-C.sub.6)-alkenyl, (C.sub.2-C.sub.6)-alkynyl, (C.sub.2-C.sub.6)-haloalkynyl, (C.sub.2-C.sub.6)-alkynylcarbonyl, (C.sub.2-C.sub.6)-haloalkynylcarbonyl, (C.sub.2-C.sub.6)-alkynyloxy, (C.sub.2-C.sub.6)-haloalkynyloxy, (C.sub.2-C.sub.6)-alkynyloxycarbonyl and (C.sub.2-C.sub.6)-haloalkynyloxycarbonyl and nitro; X is a bond (if n=1 or n=2), CH.sub.2, O, S, carbonyl, NH, CR.sup.12R.sup.13 and NR.sup.14 or CH.sub.2O, CH.sub.2S, where the carbon atom in the two latter groups is bonded to the aromatic moiety and the heteroatom O or S to the partly hydrogenated amine moiety; and R.sup.12 and R.sup.13 are each independently selected from the group consisting of hydrogen, (C.sub.1-C.sub.6)-alkyl and (C.sub.1-C.sub.6)-haloalkyl, and R.sup.14 is selected from the group consisting of hydrogen, (C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-haloalkyl said process comprising condensing an amidine of the (IV) type or an acid addition salt thereof ##STR00022## with a ketone of the formula (V) ##STR00023## in which the Z.sup.3 radical is a (C.sub.1-C.sub.6)-alkoxy or di-(C.sub.1-C.sub.6)-alkylamino.

20. A herbicidal composition or plant growth-regulating composition, comprising one or more compounds of formula (I) and/or one or more salts thereof as claimed in claim 1.

21. A method of controlling harmful plants or of regulating the growth of plants, comprising applying an effective amount of one or more compounds of formula (I) or one or more salts thereof as claimed in claim 1 to one or more plants, plant parts, plant seeds or an area under cultivation.

22. A product comprising one or more compounds of formula (I) or one or more salts thereof as claimed in claim 1 as herbicides or as plant growth regulators.

23. The product as claimed in claim 22, wherein the one or more compounds of formula (I) or one or more salts thereof are adapted in said product to be used to control harmful plants or to regulate the growth of plants in crops of useful plants or ornamental plants.

24. The product as claimed in claim 23, wherein the crop plants are transgenic crop plants.

Description

A. SYNTHESIS EXAMPLES

1-{2-[(1R)-1,2,3,4-tetrahydronaphthalen-1-ylamino]pyrimidin-5-yl}ethanone (ex.:1.3)

[0280] 2.50 g (10.3 mmol) of 2-chloro-5-iodopyrimidine, 1.99 g (13.5 mmol) of (1R)-1,2,3,4-tetrahydronaphthalen-1-amine and 4.34 g (20.7 mmol) of dicyclohexylethylamine in 4.0 mL of 1-methyl-2-pyrrolidone are heated to 160 C. in a closed cuvette in the microwave for 90 minutes (Biotage Initiator, http://www.biotage.com/product-page/biotage-initiator). The crude mixture thus obtained is applied to silica gel and purified by column chromatography with heptane/ethyl acetate as the eluent. Concentration affords 4.00 g of 5-iodo-N-[(1R)-1,2,3,4-tetrahydronaphthalen-1-yl]pyrimidin-2-amine (in waxy form) (98% yield at 90% purity).

[0281] 2.00 g (5.12 mmol) of 5-iodo-N-[(1R)-1,2,3,4-tetrahydronaphthalen-1-yl]pyrimidin-2-amine (90% purity), 1.07 g (10.2 mmol) of trimethylsilylacetylene, 0.05 g (0.07 mol) of bis(triphenylphosphine)palladium(II) chloride, 0.02 g (0.10 mol) of copper(I) iodide and 2.18 g (20.4 mol) of triethylamine in 3.0 mL of N,N-dimethylformamide are stirred at 70 C. for 6 hours. The crude mixture thus obtained is applied to silica gel and purified by column chromatography with heptane/ethyl acetate as the eluent. Concentration affords 1.30 g of N-[(1R)-1,2,3,4-tetrahydronaphthalen-1-yl]-5-[(trimethylsilyl)ethynyl]pyrimidin-2-amine (in waxy form) (75% yield at 95% purity).

[0282] 1.30 g (4.04 mmol) of N-[(1R)-1,2,3,4-tetrahydronaphthalen-1-yl]-5-[(trimethylsilyl)ethynyl]pyrimidin-2-amine, 0.139 g (0.81 mmol) of 4-toluenesulfonic acid and 8.69 g (188.6 mol) of ethanol are heated to 120 C. in a closed cuvette in the microwave for 30 minutes (Biotage Initiator, http://www.biotage.com/product-page/biotage-initiator). The crude mixture thus obtained is applied to silica gel and purified by column chromatography with heptane/ethyl acetate as the eluent. Concentration affords 0.80 g of 1-{2-[(1R)-1,2,3,4-tetrahydronaphthalen-1-ylamino]pyrimidin-5-yl}ethanone (solid, m.p.: 128.2 C.) (70% yield at 95% purity).

1-{4-methyl-2-[(1R)-1,2,3,4-tetrahydronaphthalen-1-ylamino]pyrimidin-5-yl}ethanone (ex.:1.10)

Method A:

[0283] 1.00 g (5.17 mmol) of 2-chloro-5-bromopyrimidine, 1.17 g (7.24 mmol) of (1R,2S)-2,6-dimethyl-2,3-dihydro-1H-inden-1-amine and 2.14 g (15.5 mmol) of potassium carbonate in 2.5 mL of 1-methyl-2-pyrrolidone are heated to 180 C. in a closed cuvette in the microwave for 180 minutes (Biotage Initiator, http://www.biotage.com/product-page/biotage-initiator). The crude mixture thus obtained is applied to silica gel and purified by column chromatography with heptane/ethyl acetate as the eluent. Concentration affords 1.39 g of 5-bromo-N-[(1R,2S)-2,6-dimethyl-2,3-dihydro-1H-inden-1-yl]pyrimidin-2-amine (in waxy form) (80% yield at 95% purity).

Method B:

[0284] 2.5 g (12.9 mmol) of 2-chloro-5-bromopyrimidine, 2.50 g (15.5 mmol) of (1R,2S)-2,6-dimethyl-2,3-dihydro-1H-inden-1-amine and 2.61 g (25.8 mmol) of triethylamine in 6 mL of dioxane are heated to 120 C. in a closed cuvette in the microwave for 120 minutes (http://www.biotage.com/product-page/biotage-initiator). The crude mixture thus obtained is applied to silica gel and purified by column chromatography with heptane/ethyl acetate as the eluent. Concentration affords 3.30 g of 5-bromo-N-[(1R,2S)-2,6-dimethyl-2,3-dihydro-1H-inden-1-yl]pyrimidin-2-amine (in waxy form) (68% yield at 85% purity).

[0285] 0.80 g (2.51 mmol) of 5-bromo-N-[(1R,2S)-2,6-dimethyl-2,3-dihydro-1H-inden-1-yl]pyrimidin-2-amine, 0.49 g (5.03 mmol) of trimethylsilylacetylene, 0.1 g (0.14 mol) of bis(triphenylphosphine)palladium(II) chloride, 0.02 g (0.10 mol) of copper(I) iodide and 1.45 g (13.6 mol) of triethylamine are stirred at 80 C. for 8 hours. The crude mixture thus obtained is applied to silica gel and purified by column chromatography with heptane/ethyl acetate as the eluent. Concentration affords 0.88 g of N-[(1R,2S)-2,6-dimethyl-2,3-dihydro-1H-inden-1-yl]-5-[(trimethylsilyl)ethynyl]pyrimidin-2-amine (in waxy form) (99% yield at 95% purity).

[0286] 0.32 g (0.95 mmol) of N-[(1R,2S)-2,6-dimethyl-2,3-dihydro-1H-inden-1-yl]-5-[(trimethylsilyl)ethynyl]pyrimidin-2-amine, 0.03 g (0.19 mmol) of 4-toluenesulfonic acid and 1.58 g (34.3 mol) of ethanol are heated to 120 C. in a closed cuvette in the microwave for 30 minutes (Biotage Initiator, http://www.biotage.com/product-page/biotage-initiator). The crude mixture thus obtained is applied to silica gel and purified by column chromatography with heptane/ethyl acetate as the eluent. Concentration affords 0.16 g of N-[(1R,2S)-2,6-dimethyl-2,3-dihydro-1H-inden-1-yl]-5-[(trimethylsilyl)ethynyl]pyrimidin-2-amine (solid; m.p. 127.5 C.) (58% yield at 95% purity).

1-{4-methyl-2-[(1R)-1,2,3,4-tetrahydronaphthalen-1-ylamino]pyrimidin-5-yl}ethanone (ex.:1.82)

[0287] 0.20 g (1.10 mmol) of 1-(4-methyl-2-methylsulfanylpyrimidin-5-yl)ethanone and 0.485 g (3.30 mmol) of (1R)-1,2,3,4-tetrahydronaphthalen-1-amine in 1.5 mL of 1-methyl-2-pyrrolidone are heated to 180 C. in a closed cuvette in the microwave for 180 minutes (Biotage Initiator, http://www.biotage.com/product-page/biotage-initiator). The crude mixture thus obtained is applied to silica gel and purified by column chromatography with heptane/ethyl acetate as the eluent. Concentration affords 0.037 g of 1-{4-methyl-2-[(1R)-1,2,3,4-tetrahydronaphthalen-1-ylamino]pyrimidin-5-yl}ethanone (in waxy form) (11% yield at 95% purity).

1-[2-(3,4-Dihydro-2H-chromen-4-ylamino)-4-methylpyrimidin-5-yl]ethanone (ex.:1.83)

[0288] 0.22 g (1.21 mmol) of 1-[4-methyl-2-(methylsulfanyl)pyrimidin-5-yl]ethanone is initially charged in 7 mL of dichloromethane and cooled down to about 0-5 C., then 0.428 g (1.81 mmol) of meta-chloroperbenzoic acid (73%) is added while stirring. The mixture is then stirred for 2 hours and allowed to come to room temperature (about 20 C.) within that period. Subsequently, 0.252 g (1.69 mmol) of 3,4-dihydro-2H-chromen-4-amine and 0.643 g (6.04 mmol) of triethylamine are added. This reaction mixture is stirred at room temperature for about 3 hours and left to stand overnight. The crude mixture thus obtained is applied to silica gel and purified by column chromatography with heptane/ethyl acetate as the eluent. Concentration affords 0.191 g of 1-[2-(3,4-dihydro-2H-chromen-4-ylamino)-4-methylpyrimidin-5-yl]ethanone (solid, m.p.: 170.6 C.) (53% yield at 95% purity).

7,7-dimethyl-2-[(1R)-1,2,3,4-tetrahydronaphthalen-1-ylamino]-7,8-dihydroquinazolin-5(6H)-one (ex.:2.25)

[0289] 2.00 g (14.2 mmol) of dimedone, 1.70 g (14.2 mmol) of N,N-dimethylformamide dimethyl acetal, 1.70 g (14.2 mmol) of dicyclohexylmethylamine and 2.00 g (7.14 mmol) of S-methylisothiourea sulfate in 5 mL of 1-methyl-2-pyrrolidone are heated to 180 C. in a closed cuvette in the microwave for 100 minutes. The crude mixture thus obtained is applied to silica gel and purified by column chromatography with heptane/ethyl acetate as the eluent. Concentration affords 1.35 g of 7,7-dimethyl-2-(methylsulfanyl)-7,8-dihydroquinazolin-5(6H)-one (solid) (40% yield at 95% purity).

[0290] 0.18 g (0.87 mmol) of 7,7-dimethyl-2-(methylsulfanyl)-7,8-dihydroquinazolin-5(6H)-one is initially charged in 4 mL of dichloromethane and cooled down to about 0-5 C., then 0.383 g (1.61 mmol) of meta-chloroperbenzoic acid (73%) is added while stirring. The mixture is then stirred for 2 hours and allowed to come to room temperature (about 20 C.) within that period. Subsequently, 0.179 g (1.21 mmol) of (1R)-1,2,3,4-tetrahydronaphthalen-1-amine and 0.431 g (4.04 mmol) of triethylamine are added. This reaction mixture is stirred at room temperature for about 3 hours and left to stand overnight. The crude mixture thus obtained is applied to silica gel and purified by column chromatography with heptane/ethyl acetate as the eluent. Concentration affords 0.252 g of 7,7-dimethyl-2-[(1R)-1,2,3,4-tetrahydronaphthalen-1-ylamino]-7,8-dihydroquinazolin-5(6H)-one (in waxy form) (92% yield at 95% purity).

TABLE-US-00004 TABLE 3 (physicochemical characterization of selected synthesis examples) Compound Description 1.3 solid, m.p.: 128-129 C.; logp (HCOOH): 2.51; 8.65 + 8.80 (2s, 1H, Pyr-6H); 1.4 oily; logp (HCOOH): 2.03; 1H-NMR (CDCL.sub.3, 400 MHZ, in ppm): 2.15 (m, 1H, 1H from CH.sub.2); 2.25 (s, 3H, CH.sub.3); 2.30 (m, 1H, 1H from CH.sub.2); 2.40 (s, 3H, CH.sub.3); 4.30 (m, 2H, 2H from CH.sub.2O); 5.35 (br, 1H, CH); 6.70 (br, 1H, NH); 6.90-7.00 (m, 2H, ArH); 7.20-7.35 (m, 2H, ArH); 8.20 + 8.90 (2s, 2H, Pyr-4H, Pyr-6H); 1.7 solid; m.p.: 167-168 C.; logp (HCOOH): 2.54; 1H-NMR (CDCl.sub.3, 400 MHZ, in ppm): 2.15 (m, 1H, 1H from CH.sub.2); 2.25 (s, 3H, CH.sub.3); 2.30 (m, 1H, 1H from CH.sub.2); 2.45 (s, 3H, CH.sub.3); 4.25 (m, 2H, 2H from CH.sub.2O); 5.35 (br, 1H, CH); 6.80-6,90 (m, 1H, ArH); 7.10-7.20 (m, 2H, ArH); 7.25 (br, 1H, NH); 8.15 + 8.90 (2s, 2H, Pyr-4H, Pyr-6H); 1.8 solid; m.p.: 181-182 C.; logp (HCOOH): 2.94; 1H-NMR (CDCl.sub.3, 400 MHZ, in ppm): 2.15 (m, 1H, 1H from CH.sub.2); 2.20 (s, 3H, CH.sub.3); 2.25 (s, 3H, CH.sub.3); 2.30 (m, 1H, 1H from CH.sub.3); 2.45 (s, 3H, CH.sub.3); 4.25 (m, 2H, 2H from CH.sub.3O); 5.25 (br, 1H, CH); 6.80 (br, 1H, NH); 6,90 (m, 2H, ArH); 8.45 + 8.90 (2s, 2H, Pyr-4H, Pyr-6H); 1.10 solid; m.p.: 127-128 C.; logp (HCOOH): 2.99; 1H-NMR (CDCl.sub.3, 400 MHZ, in ppm): 1.25 (d, 3H, CH.sub.3); 1.70 (m, 2H, 2H from CH.sub.2); 1.95 (m, 2H, 2H from CH.sub.2); 2.45 (m, 3H, CH.sub.3); 2.85 (m, 1H, 1H from CH); 5.35 (br, 1H, CH); 5.90 (br, 1H, NH); 6.95-7.10 (m, 3H, ArH); 8.80 + 8.90 (2s, 1H, Pyr-6H); 1.20 oily; logp (HCOOH): 2.93; 1H-NMR (CDCl.sub.3, 400 MHZ, in ppm): 1.05 (d, 3H, CH.sub.3); 2.30 (s, 3H, CH.sub.3); 2.35 (m, 1H, 1H from CH.sub.2); 2.45 (m, 3H, CH.sub.3); 2.50 (m, 1H, 1H from CH.sub.2); 3.05 (m, 1H, 1H from CH); 5.15 (br, 1H, CH); 6.30 (br, 1H, NH); 7.05- 7.30 (m, 4H, ArH); 8.60 + 8.90 (2s, 1H, Pyr-6H); 1.26 solid; logp (HCOOH): 3.56; 1H-NMR (CDCl.sub.3, 400 MHZ, in ppm): 1.20 (d, 3H, CH.sub.3); 2.30 (m, 3H, CH.sub.3); 2.35 (m, 1H, 1H from CH.sub.2); 2.50 (m, 3H, CH.sub.3); 2.55 (m, 1H, 1H from CH.sub.2); 2.70 (m, 3H, CH.sub.3); 3.05 (m, 1H, 1H from CH); 5.35 (br, 1H, CH); 5.90 (br, 1H, NH); 6.95-7.10 (m, 3H, ArH); 8.65 + 8.80 (2s, 1H, Pyr-6H); 1.65 solid; logp (HCOOH): 2.93; 1H-NMR (CDCl.sub.3, 400 MHZ, in ppm): 2.20 (m, 1H, 1H from CH.sub.2); 2.45 (s, 3H, CH.sub.3); 2.65 (m, 1H, 1H from CH.sub.2); 2.70 (s, 3H, CH.sub.3); 3.10 (m, 2H, 2H from CH.sub.2S); 5.45 (br, 1H, CH); 5.90 (br, 1H, NH); 6,90-7.20 (m, 3H, ArH); 8.65 + 8.80 (1s, 1H, Pyr-6H); 1.82 solid; logp (HCOOH): 3.03; 1H-NMR (CDCl.sub.3, 400 MHZ, in ppm): 1.95 (m, 3H, 2H from CH.sub.2, 1H from CH.sub.2); 2.10 (m, 1H, 1H from CH.sub.2); 2.50 (m, 3H, CH.sub.3); 2.65 + 2.,75 (2s, 3H, CH.sub.3); 2.85 (m, 2H, 2H from CH.sub.2); 5.40 (br, 1H, CH); 6.20 (br, 1H, NH); 7.10-7.30 (m, 4H, ArH); 8.60 + 8.80 (2s, 1H, Pyr-6H); 1.83 solid; m.p.: 170.6 C.; logp (HCOOH): 2.44; 1H-NMR (CDCl.sub.3, 400 MHZ, in ppm): 2.15 (m, 1H, 1H from CH.sub.2); 2.30 (m, 1H, 1H from CH.sub.2); 2.50 (br, 3H, CH.sub.3); 2.65 (br, 3H, CH.sub.3); 4.25 (m, 2H, 2H from CH.sub.2O); 5.35 (br, 1H, CH); 5.80 + 6.40 (br, 1H, NH); 6.90 (m, 2H, ArH); 7.20-7.30 (m, 2H, ArH); 8.40 + 8.80 (2s, 1H, Pyr-6H); 1.85 oily; logp (HCOOH): 4,65; 1H-NMR (CDCl.sub.3, 400 MHZ, in ppm): 0,95 (t, 3H, CH.sub.3); 1.25 (d, 3H, CH.sub.3); 1,40 (m, 2H, 2H from CH.sub.2); 1,75 (m, 2H, 2H from CH.sub.2); 2.30 (s, 3H, CH.sub.3); 2.35 (m, 1H, 1H from CH.sub.2); 2.55 (m, 1H, 1H from CH.sub.2); 2.70 (m, 3H, CH.sub.3); 2,80 (m, 2H, 2H from CH.sub.2); 3.05 (m, 1H, 1H from CH); 5.35 (br, 1H, CH); 5.80 (br, 1H, NH); 6.95-7.10 (m, 3H, ArH); 8.80 + 8.95 (2s, 2H, Pyr-4H, Pyr-6H); 1.86 oily; logp (HCOOH): 4,14; 1H-NMR (CDCl.sub.3, 400 MHZ, in ppm): 0,20 (m, 2H, 2H from CH.sub.2 in Cyclpropyl); 0,60 (m, 2H, 2H from CH.sub.2 in Cyclpropyl); 1,10 (m, 1H, 1H from CH in Cyclpropyl); 1.25 (d, 3H, CH.sub.3); 2.30 (s, 3H, CH.sub.3); 2.35 (m, 1H, 1H from CH.sub.2); 2.55 (m, 1H, 1H from CH.sub.2); 2.75 (m, 2H, CH.sub.2); 3.05 (m, 1H, 1H from CH); 5.35 (br, 1H, CH); 5.90 (br, 1H, NH); 6.95-7.10 (m, 3H, ArH); 8.75 + 8.90 (2s, 2H, Pyr-4H, Pyr-6H); 1.87 solid; m.p.: 127,2C.; logp (HCOOH): 3,12; 1H-NMR (CDCl.sub.3, 400 MHZ, in ppm): 2.15 (m, 1H, 1H from CH.sub.2); ); 2.20 (s, 3H, CH.sub.3); 2.30 (m, 1H, 1H from CH.sub.2); 2.50 (br, 3H, CH.sub.3); 2.65 (br, 3H, CH.sub.3); 4.25 (m, 2H, 2H from CH.sub.2O); 5.35 (br, 1H, CH); 5.60 + 5.90 (br, 1H, NH); 6.80 (m, 2H, ArH); 8.60 + 8.90 (2s, 1H, Pyr-6H); 1.88 solid; m.p.: 128,3 C.; logp (HCOOH): 3,10; 1H-NMR (CDCl.sub.3, 400 MHZ, in ppm): 1.90 (m, 3H, 1H from CH.sub.2, 2H from CH.sub.2); 2.15 (m, 1H, 1H from CH.sub.2); 2.50 (br, 3H, CH.sub.3); 2.65 (br, 3H, CH.sub.3); 2,85 (m, 2H, 2H from CH.sub.2); 5.35 (br, 1H, CH); 5.60 (br, 1H, NH); 6.85 (m, 2H, ArH); 7.30 (m, 1H, ArH); 8.60 + 8.85 (2s, 1H, Pyr-6H); 1.89 solid; logp (HCOOH): 2,80; 1H-NMR (CDCl.sub.3, 400 MHZ, in ppm: 1,90 (m, 1H, 1H from CH.sub.2); 2.50 (s, 3H, CH.sub.3); 2.65 (br, 4H, CH.sub.3, 1H from CH.sub.2); 2.90 (m, 1H, 1H from CH.sub.2); 3.00 (m, 1H, 1H from CH); 5.65 (br, 1H, CH); 5.75 (br, 1H, NH); 7.10-7.3 (m, 4H, ArH); 8.70 + 8.90 (1s, 1H, Pyr-6H); 1.90 solid; m.p.: 111,5 C.; logp (HCOOH): 2,43; 1H-NMR (CDCl.sub.3, 400 MHZ, in ppm: 1,95 (m, 1H, 1H from CH.sub.2); 2.50 (s, 3H, CH.sub.3); 2.75 (m, 1H, 1H from CH.sub.2); 2.90 (m, 1H, 1H from CH.sub.2); 3.10 (m, 1H, 1H from CH); 5.75 (m, 1H, CH); 6,30 (br, 1H, NH); 6,95-7.25 (m, 3H, ArH); 8.65 + 8.95 (2s, 2H, Pyr-4H, Pyr-6H); 1.91 solid; m.p.: 130,9 C.; logp (HCOOH): 3,90; 1H-NMR (CDCl.sub.3, 400 MHZ, in ppm: 1,20 (d, 6H, 2*CH.sub.3); 1,90 (m, 1H, 1H from CH.sub.2); 2.50 (s, 3H, CH.sub.3); 2.65 (br, 4H, CH.sub.3, 1H from CH.sub.2); 2.90 (m, 2H, 1H from CH.sub.2, 1H from CH(CH.sub.3).sub.2); 3.00 (m, 1H, 1H from CH); 5.65 (br, 1H, CH); 5.75 (br, 1H, NH); 7.10-7.25 (m, 3H, ArH); 8.60 + 8.85 (1s, 1H, Pyr-6H); 1.92 solid; m.p.: 134.0 C.; logp (HCOOH): 2,93; 1H-NMR (CDCl.sub.3, 400 MHZ, in ppm): 1.90 (m, 3H, 1H from CH.sub.2, 2H from CH.sub.2); 2.10 (m, 1H, 1H from CH.sub.2); 2.50 (br, 3H, CH.sub.3); 2.65 (br, 3H, CH.sub.3); 2,85 (m, 2H, 2H from CH.sub.2); 3,80 (s, 3H, OCH.sub.3); 5.35 (br, 1H, CH); 5.60 (br, 1H, NH); 6.75 (d, 1H, ArH); 6.85 (m, 1H, ArH); 7.25 (m, 1H, ArH); 8.60 + 8.80 (2s, 1H, Pyr-6H); 1.93 solid; m.p.: 194,2 C.; logp (HCOOH): 3,14; 1H-NMR (CDCl.sub.3, 400 MHZ, in ppm: 2.15 (br, 3H, CH.sub.3); 2.25 (br, 3H, CH.sub.3); 2.50 (br, 3H, CH.sub.3); 2.65 (br, 3H, CH.sub.3); 4,40 (m, 1H, 1H from CH.sub.2); 4,80 (m, 1H, 1H from CH.sub.2); 5.65 (br, 2H, CH, NH); 6.75 (d, 1H, ArH); 7,10 (d, 1H, ArH); 8.60 + 8.85 (1s, 1H, Pyr-6H); 1.94 solid; m.p.: 157,8 C.; logp (HCOOH): 3,48; 1H-NMR (CDCl.sub.3, 400 MHZ, in ppm): 1,20 (d, 6H, 2*CH.sub.3); 2.15 (m, 1H, 1H from CH.sub.2); ); 2.30 (m, 1H, 1H from CH.sub.2); 2.50 (br, 3H, CH.sub.3); 2.65 (br, 3H, CH.sub.3); 4.25 (m, 2H, 2H from CH.sub.2O); 5.35 (br, 1H, CH); 5.60 + 5.90 (br, 1H, NH); 6.80 (m, 1H, ArH); 7,10 (m, 2H, ArH); 8.60 + 8.85 (2s, 1H, Pyr-6H); 1.95 solid; m.p.: 153.0 C.; logp (HCOOH): 3,45; 1H-NMR (CDCl.sub.3, 400 MHZ, in ppm): 1.90 (m, 3H, 1H from CH.sub.2, 2H from CH.sub.2); 2.05 (m, 1H, 1H from CH.sub.2); 2.20 (s, 3H, CH.sub.3); 2.25 (s, 3H, CH.sub.3); 2.50 (s, 3H, CH.sub.3); 2,75 (m, 2H, 2H from CH.sub.2); 5.35 (m, 1H, CH); 6,30 (br, 1H, NH); 6.95 (d, 1H, ArH); 7,00 (d, 1H, ArH); 8.60 + 8.90 (2s, 2H, Pyr-4H, Pyr-6H); 1.96 solid; m.p.: 183,5 C.; logp (HCOOH): 3,12; 1H-NMR (CDCl.sub.3, 400 MHZ, in ppm): 1,35 (s, 3H, CH.sub.3); 1,45 (s, 3H, CH.sub.3); 1,80 (m, 1H, 1H from CH.sub.2); ); 2.30 (m, 1H, 1H from CH.sub.2); 2.50 (br, 3H, CH.sub.3); 2.65 (br, 3H, CH.sub.3); 3,75 (s, 3H, OCH.sub.3; 5.45 (br, 1H, CH); 5.55 + 5.75 (br, 1H, NH); 6.40 (s, 1H, ArH); 6.50 (m, 1H, ArH); 7,15 (m, 1H, ArH); 8.60 + 8.85 (2s, 1H, Pyr-6H); 2.13 oily; logp (HCOOH): 3.03; 1H-NMR (CDCl.sub.3, 400 MHZ, in ppm): 1.95 (m, 3H, 2H from CH.sub.2, 1H from CH.sub.2); 2.15 (m, 3H, 2H from CH.sub.2, 1H from CH.sub.2); 2.55 (m, 2H, 2H from CH.sub.2); 2.70-2,90 (m, 4H, 2H from CH.sub.2, 2H from CH.sub.2); 5.45 (br, 1H, CH); 5.80 + 5.90 (br, 1H, NH); 6,95 (m, 1H, ArH); 7.15 (m, 2H, ArH); 8.80 + 8,85 (2s, 1H, Pyr-6H); 2.19 oily; logp (HCOOH): 2,29; 1H-NMR (CDCl.sub.3, 400 MHZ, in ppm): 2.15 (m, 3H, 2H from CH.sub.2, 1H from CH.sub.2); 2.30 (m, 1H, 1H from CH.sub.2); 2.55 (m, 2H, 2H from CH.sub.2); 2.70-2,90 (m, 2H, 2H from CH.sub.2); 4,30-4,45 (m, 2H, 2H from CH.sub.2); 5.45 (m, 1H, CH); 5.80 + 5.90 (br, 1H, NH); 6,95 (m, 1H, ArH); 7.05 (m, 2H, ArH); 8.80 + 8,85 (2s, 1H, Pyr-6H); 2.23 solid; m.p.: 137.4 C.; logp (HCOOH): 2.93; 1H-NMR (CDCl.sub.3, 400 MHZ, in ppm): 1.95 (m, 3H, 2H from CH.sub.2, 1H from CH.sub.2); 2.15 (m, 3H, 2H from CH.sub.2, 1H from CH.sub.2); 2.55 (m, 2H, 2H from CH.sub.2); 2.80-3.00 (m, 4H, 2H from CH.sub.2, 2H from CH.sub.2); 5.45 (br, 1H, CH); 5.80 + 5.90 (br, 1H, NH); 7.10-7.30 (m, 4H, ArH); 8.80 + 9.00 (2s, 1H, Pyr-6H); 2.25 oily; logp (HCOOH): 3.71; 1H-NMR (CDCl.sub.3, 400 MHZ, in ppm): 1.10 (m, 6H, 2*CH.sub.3); 1.95 (m, 3H, 2H from CH.sub.2, 1H from CH.sub.2); 2.15 (m, 1H, 1H from CH.sub.2); 2.45 (s, 2H, 2H from CH.sub.2); 2.65 + 2.80 (2s, 2H, 2H from CH.sub.2); 2.85 (m, 2H, 2H from CH.sub.2); 5.45 (br, 1H, CH); 5.80 (br, 1H, NH); 7.10-7.30 (m, 4H, ArH); 8.80 + 8.95 (2s, 1H, Pyr-6H); 2.26 oily; logp (HCOOH): 3.45; 1H-NMR (CDCl.sub.3, 400 MHZ, in ppm): 1.15 (m, 3H, CH.sub.3); 1.95 (m, 3H, 2H from CH.sub.2, 1H from CH.sub.2); 2.15 (m, 1H, 1H from CH.sub.2); 2.25-2.85 (m, 7H); 5.45 (br, 1H, CH); 5.80 + 5.90 (2br, 1H, NH); 7.10-7.30 (m, 4H, ArH); 8.75 + 8.95 (2s, 1H, Pyr-6H); 2.34 oily; logp (HCOOH): 3.37; 1H-NMR (CDCl.sub.3, 400 MHZ, in ppm): 2.38 oily; logp (HCOOH): 4.84; 1H-NMR (CDCl.sub.3, 400 MHZ, in ppm): 1,85 (m, 1H, 1H from CH.sub.2); 2.15 (m, 2H, CH.sub.2); 2.30 (m, 3H, 3H from CH.sub.3); 2.55 (m, 2H, 2H from CH.sub.2); 2.80 + 2.85 (m, 4H, 2*2H from CH.sub.2); 5.70 (br, 2H, 1H from CH, 1H from NH); 7,05-7.20 (m, 3H, ArH); 8.80 + 8.95 (2s, 1H, Pyr-6H); 2.41 oily; logp (HCOOH): 3.21; 1H-NMR (CDCl.sub.3, 400 MHZ, in ppm): 1.95 (m, 1H, 1H from CH.sub.2); 2.15 (m, 2H, 2H from CH.sub.2); 2.55 (m, 2H, 2H from CH.sub.2); 2.65 (m, 2H, 2H from CH.sub.2); 2.70 (m, 1H, 1H from CH.sub.2); 2.90 (m, 2H, 2H from CH.sub.2); 3.05 (m, 1H, 1H from CH.sub.2); 5.70 (br, 1H, CH); 5.85 + 5.95 (br, 1H, NH); 7.15-7.35 (m, 4H, ArH); 8.65 + 8,95 (2s, 1H, Pyr-6H); 2.43 solid; logp (HCOOH): 3.45; 1H-NMR (CDCl.sub.3, 400 MHZ, in ppm): 1.25 (t, 3H, CH.sub.3); 2.15 (m, 2H, CH.sub.2); 2.30 (m, 4H, 3H from CH.sub.3, 1H from CH.sub.2); 2.55 (m, 3H, 1H from CH.sub.2, 2H from CH.sub.2); 2.80 + 2.85 (2m, 2H, 2H from CH.sub.2); 3.05 (m, 1H, 1H from CH); 5.40 (br, 1H, CH); 6.00 (br, 1H, NH); 6.95-7.10 (m, 3H, ArH); 8.80 + 8.95 (2s, 1H, Pyr-6H); 2.44 oily; logp (HCOOH): 3.90; 2.45 oily; logp (HCOOH): 4.23; 1H-NMR (CDCl.sub.3, 400 MHZ, in ppm): 1.10 (m, 6H, 2*CH.sub.3); 1.25 (t, 3H, CH.sub.3); 2.30 (m + s, 4H, 3H, CH.sub.3, 1H from CH.sub.2); 2.45 (s, 2H, 2H from CH.sub.2); 2.55 (m, 1H, 1H from CH.sub.2); 2.70 + 2.80 (2s, 2H, 2H from CH.sub.2); 3.05 (m, 1H, 1H from CH.sub.2); 5.40 (t, 1H, CH); 5.70 (br, 1H, NH); 7.00-7.15 (m, 3H, ArH); 8.80 + 8.95 (2s, 1H, Pyr-6H); 2.46 oily; logp (HCOOH): 3.24; 1H-NMR (CDCl.sub.3, 400 MHZ, in ppm): 1.25 (t, 3H, CH.sub.3); 2.30 (m + s, 4H, 3H, CH.sub.3, 1H from CH.sub.2); 2.50 (m, 2H, 1H from CHCF.sub.3,.sub.- 1H from CH.sub.2); 2.70-3.10 (m, 5H, 1H from CH.sub.2, 2H from CH.sub.2, 2H from CH.sub.2); 5.35 (m, 1H, CH); 5.70 (br, 1H, NH); 7.00-7.15 (m, 3H, ArH); 8.85 + 8.95 (2s, 1H, Pyr-6H); 2.50 oily; logp (HCOOH): 4.86; 1H-NMR (CDCl.sub.3, 400 MHZ, in ppm): 1.25 (t, 3H, CH.sub.3); 2.30 (m + s, 4H, 3H, CH.sub.3, 1H from CH.sub.2); 2.50 (m, 1H, 1H from CH.sub.2); 2.85 (m, 2H, 2H from CH.sub.2); 3.10 (m, 3H, 1H from CH.sub.2, 2H from CH.sub.2); 3.85 (m, 1H, 1H from CHPh); 5.35 (m, 1H, CH); 5.80 (br, 1H, NH); 7.00-7.30 (m, 7H, ArH); 8.85 + 9.00 (2s, 1H, Pyr-6H); 2.52 oily; logp (HCOOH): 4.87; 1H-NMR (CDCl.sub.3, 400 MHZ, in ppm): 1.25 (t, 3H, CH.sub.3); 2.30 (m + s, 4H, 3H, CH.sub.3, 1H from CH.sub.2); 2.50 (m, 1H, 1H from CH.sub.2); 2.70-2.90 (m, 2H, 2H from CH.sub.2); 3.10 (m, 3H, 1H from CH.sub.2, 2H from CH.sub.2); 3.50 (m, 1H, 1H from CHPh), 5.35 (m, 1H, CH); 5.80 (br, 1H, NH); 7.00-7.30 (m, 7H, ArH); 8.85 + 9.00 (2s, 1H, Pyr-6H); 2.84 oily; logp (HCOOH): 2.75; 1H-NMR (CDCl.sub.3, 400 MHZ, in ppm): 2.15 (m, 3H, 2H from CH.sub.2, 1H from CH.sub.2); ); 2.25 (m, 1H, 1H from CH.sub.2); 2.55 (q, 2H, 2H from CH.sub.2); 2.70-2.85 (m, 2H, 2H from CH.sub.2); 4.25 (m, 1H, 1H from CH.sub.2O); 4.40 (m, 1H, 1H from CH.sub.2O; 5.70 (br, 1H, CH); 5.85 (br, 1H, NH); 6.80 (m, 1H, ArH); 7,10 (m, 1H, ArH); 7,20 (m, 1H, ArH); 8.70 + 8.90 (2s, 1H, Pyr-6H); 2.91 oily; logp (HCOOH): 2.62; 1H-NMR (CDCl.sub.3, 400 MHZ, in ppm): 1.25 (m, 1H, 1H from CH.sub.2); 1.90 (m, 1H, 1H from CH.sub.2); 2.15 (m, 2H, CH.sub.2); 2.55 (q, 2H, 2H from CH.sub.2); 2.70 (m, 1H, 1H from CH.sub.2); 2.80-3.05 (m, 3H, 2H from CH.sub.2, 1H from CH.sub.2); 5.70 (br, 2H, CH, NH); 7.15-7.30 (m, 4H, ArH); 8.80 + 8.95 (2s, 1H, Pyr-6H); 2.92 oily; logp (HCOOH): 4.05; 1H-NMR (CDCl.sub.3, 400 MHZ, in ppm): 1.95 (m, 3H, 2H from CH.sub.2, 1H from CH.sub.2); 2.15 (m, 1H, 1H from CH.sub.2); 2.70-2.90 (m, 5H, 2*2H from CH.sub.2, 1H from CH.sub.2); 3.00-3.15 (m, 2H, 2*1H from CH.sub.2); 3.50 (m, 1H, 1H from CHPh), 5.45 (m, 1H, CH); 5.85 (br, 1H, NH); 7.00-7.30 (m, 7H, ArH); 8.85 + 9.00 (2s, 1H, Pyr-6H); 2.93 oily; logp (HCOOH): 4.38; 1H-NMR (CDCl.sub.3, 400 MHZ, in ppm): 1.95 (m, 3H, 2H from CH.sub.2, 1H from CH.sub.2); 2.15 (m, 1H, 1H from CH.sub.2); 2.70-2.90 (m, 5H, 2*2H from CH.sub.2, 1H from CH.sub.2); 3.00-3.15 (m, 2H, 2*1H from CH.sub.2); 3.75 (m, 1H, 1H from CHPh), 5.45 (m, 1H, CH); 5.95 (br, 1H, NH); 7.00-7.30 (m, 7H, ArH); 8.85 + 9.00 (2s, 1H, Pyr-6H); 2.94 oily; logp (HCOOH): 2.97; 1H-NMR (CDCl.sub.3, 400 MHZ, in ppm): 1.10 (s, 6H, 2*CH.sub.3); 2.15 (m, 1H, 1H from CH.sub.2); 2.30 (m, 1H, 1H from CH.sub.2); 2.45 (s, 2H, 2H from CH.sub.2);, 2.65 (m, 1H, 1H from CH.sub.2); 2.80 (m, 1H, 1H from CH.sub.2); 4.25 (m, 2H, 2H from CH.sub.2O); 5.35 (m, 1H, CH); 5.85 (br, 1H, NH); 6.90 (m, 2H, ArH); 7.25 (m, 2H, ArH); 8.80 + 8.95 (2s, 1H, Pyr-6H); 2.95 oily; logp (HCOOH): 4.02; 1H-NMR (CDCl.sub.3, 400 MHZ, in ppm): 1.10 (s + d, 9H, 2*CH.sub.3, CH.sub.3); 1.75 (m, 1H, 1H from CH.sub.2); 1.95 (m, 2H, 21H from CH.sub.2); 2.45 (s, 2H, 2H from CH.sub.2); 2.65 (m, 1H, 1H from CH.sub.2); 2.75 (m, 1H, 1H from CH.sub.2); 2.85 (s, 2H, 2H from CH.sub.2); 5.15 (m, 1H, CH); 5.65 (br, 1H, NH); 7.05-7.30 (m, 4H, ArH); 8.80 + 8.95 (2s, 1H, Pyr-6H); 2.96 oily; logp (HCOOH): 3.71; 1H-NMR (CDCl.sub.3, 400 MHZ, in ppm): ): 1.95 (m, 3H, 2H from CH.sub.2, 1H from CH.sub.2); 2.15 (m, 1H, 1H from CH.sub.2); 2.60 (m, 1H, 1H from CH.sub.2); 2.75-3.15 (m, 7H, 3*2H from CH.sub.2, 1H from CH.sub.2); 5.40 (m, 1H, CH); 5.95 (br, 1H, NH); 7.05-7.30 (m, 4H, ArH); 8.80 + 9.00 (2s, 1H, Pyr-6H); 2.97 oily; logp (HCOOH): 3.26; 1H-NMR (CDCl.sub.3, 400 MHZ, in ppm): ): 1.25 (t, 3H, CH.sub.3); 2.30 (m + s, 4H, 3H, CH.sub.3, 1H from CH.sub.2); 2.55 (m, 1H, 1H from CH.sub.2); 3.10 (m, 3H, 1H from CH.sub.2); 4.30 (s, 2H, 2H from CH.sub.2O); 4.65 (s, 1H, 2H from CH.sub.2); 4.75 (s, 1H, 2H from CH.sub.2); 5.40 (m, 1H, CH); 5.85 (br, 1H, NH); 7.00-7.15 (m, 3H, ArH); 8.85-8.95 (2s, 1H, Pyr-6H); 2.99 oily; logp (HCOOH): 4.86; 1H-NMR (CDCl.sub.3, 400 MHZ, in ppm): ): 1.25 (t, 3H, CH.sub.3); 1.50 (m, 2H, 2H from CH.sub.2); 1.70 (m, 2H, 2H from CH.sub.2); 2.30 (m + s, 4H, 3H, CH.sub.3, 1H from CH.sub.2); 2.55 (m, 3H, 1H from CH.sub.2, 2H from CH.sub.2); 2.85 (m, 2H, 2H from CH.sub.2); 3.10 (m, 3H, 1H from CH.sub.2); 5.40 (m, 1H, CH); 5.65 (br, 1H, NH); 7.00-7.15 (m, 3H, ArH); 8.85 + 8.95 (2s, 1H, Pyr-6H); 2.100 solid; m.p.: 168.4 C.; logp (HCOOH): 2.80; 1H-NMR (CDCl.sub.3, 400 MHZ, in ppm): 2.15 (m, 3H, 2H from CH.sub.2, 1H from CH.sub.2); ); 2.20 (s, 3H, 3H from CH.sub.3); 2.25 (m, 1H, 1H from CH.sub.2); 2.55 (q, 2H, 2H from CH.sub.2); 2.70-2.85 (m, 2H, 2H from CH.sub.2); 4.25 (m, 1H, 1H from CH.sub.2O); 4.35 (m, 1H, 1H from CH.sub.2O); 5.70 (br, 1H, CH); 5.95 (br, 1H, NH); 6.80 (m, 1H, ArH); 7,10 (m, 2H, ArH); 8.80 + 8.95 (2s, 1H, Pyr-6H); 2.101 oily; logp (HCOOH): 3.00; 1H-NMR (CDCl.sub.3, 400 MHZ, in ppm): 1.90 (m, 7H, 1H from CH.sub.2, 3*2H from CH.sub.2); 2.35 (br, 3H, CH.sub.3); 2.70 (m, s, 3H, 1H from CH.sub.2, 2H from CH.sub.2); 2.80-3.05 (m, 4H, 2*2H from CH.sub.2); 5.65 (br, 2H, 1H from CH, 1H from NH); 6.85 (m, 2H, ArH); 7.25 (m, 1H, ArH); 8.80 + 8.95 (2s, 1H, Pyr-6H); 2.102 oily; 2.103 oily; 2.104 oily; 2.105 oily; logp (HCOOH): 4.14; 1H-NMR (CDCl.sub.3, 400 MHZ, in ppm): ): 1.25 (t, 3H, CH.sub.3); 1.50 (m, 2H, 2H from CH.sub.2); 1.70 (m, 2H, 2H from CH.sub.2); 2.30 (m + s, 4H, 3H, CH.sub.3, 1H from CH.sub.2); 2.55 (m, 3H, 1H from CH.sub.2, 2H from CH.sub.2); 2.85 (m, 2H, 2H from CH.sub.2); 3.10 (m, 3H, 1H from CH.sub.2); 5.40 (m, 1H, CH); 5.65 (br, 1H, NH); 7.05-7.15 (m, 3H, ArH) ; 8.80 + 8.95 (2s, 1H, Pyr-6H); 2.106 oily; logp (HCOOH): 3.90; 1H-NMR (CDCl.sub.3, 400 MHZ, in ppm): 0.95 (t, 3H, CH.sub.3); 1.80 (m, 1H, 1H from CH.sub.2); 2.15 (m, 3H, 2H from CH.sub.2, 1H from CH.sub.2), 2.30 (br, 3H, CH.sub.3); 2.50-2,60 (m, 3H, 1H from CH.sub.2, 2H from CH.sub.2), 2.80 (m, 2H, 2H from CH.sub.2); 3.05 (m, 1H, 1H from CH.sub.2); 5.50 (br, 1H, 1H from CH), 5.50 (br, 1H, 1H from NH); 7,00-7,15 (m, 3H, ArH); 8.80 + 8.95 (2s, 1H, Pyr-6H); 2.107 oily; logp (HCOOH): 3.83; 1H-NMR (CDCl.sub.3, 400 MHZ, in ppm): 1.20 (d, 6H, 2*CH.sub.3); 1.90 (m, 1H, 1H from CH.sub.2); 2.10 (m, 2H, 2H from CH.sub.2); 2.60 (m, 2H, 2H from CH.sub.2); 2.70 (m, 2H, 2H from CH.sub.2); 2.80-3.00 (m, 4H, 1H from CH(CH.sub.3).sub.2, 1H from CH.sub.2, 2H from CH.sub.2); 5.65 (br, 2H, 1H from CH) 5.80 (br, 1H, 1H from NH); 7.10- 7.25 (m, 3H, ArH); 8.80 + 8.95 (2s, 1H, Pyr-6H); 2.108 oily; logp (HCOOH): 3.58; 1H-NMR (CDCl.sub.3, 400 MHZ, in ppm): 1.25 (d, 3H, CH.sub.3); 2.15 (m, 2H, 2H from CH.sub.2); 2.55 (m, 3H, 1H from CH.sub.2, 2H from CH.sub.2); 2.70 (m, 2H, 2H from CH.sub.2); 3.10 (m, 1H, 1H from CH.sub.2); 5.35 (br, 2H, 1H from CH) 5.80 (br, 1H, 1H from NH); 7.20-7.25 (m, 3H, ArH) 8.80 + 8.95 (2s, 1H, Pyr-6H); 2.109 solid; m.p.: 151,3 C.; logp (HCOOH): 2.83; 1H-NMR (CDCl.sub.3, 400 MHZ, in ppm): 1.90 (m, 3H, 1H from CH.sub.2, 2H from CH.sub.2); 2.10 (m, 3H, 1H from CH.sub.2, 2H from CH.sub.2); 2.55 (m, 2H, 2H from CH.sub.2); 2.80-2.95 (m, 4H, 2*2H from CH.sub.2); 3.80 (s, 3H, OCH.sub.3), 5.40 (br, 1H, 1H from CH), 5.70 (br, 1H, 1H from NH); 6.65 (m, 1H, ArH), 6.75 (m, 1H, ArH); 7.20 (m, 1H, ArH); 8.80 + 8.95 (2s, 1H, Pyr-6H); 2.110 oily; logp (HCOOH): 3.98 2.111 oily; logp (HCOOH): 3.37; 1H-NMR (CDCl.sub.3, 400 MHZ, in ppm): 1.35 (d, 3H, 3H from CH.sub.3), 1.65 (m, 1H, 1H from CH.sub.2); 2.10 (m, 4H, 2*1H from CH.sub.2, 2H from CH.sub.2); 2.55 (m, 2H, 2H from CH.sub.2); 2.75-2.95 (m, 4H, 2*2H from CH.sub.2); 5.40 (br, 1H, 1H from CH), 5.80 (br, 1H, 1H from NH); 7.10-7.35 (m, 4H, ArH), 8.80 + 8.95 (2s, 1H, Pyr-6H); 2.112 oily; logp (HCOOH): 4.51; 1H-NMR (CDCl.sub.3, 400 MHZ, in ppm):, 1,50 und 1.70 (br, je 4H, je 2*2H from CH.sub.2); 1.90 (m, 1H, 1H from CH.sub.2); 2.30 (s, 3H, CH.sub.3), 2.55 (m, 2H, 2H from CH.sub.2); 2.70 (m, 2H, 2*1H from CH.sub.2); 2.80-2.95 (m, 3H, 3*1H from CH.sub.2); 5.70 (br, 1H, 1H from CH), 5.90 (br, 1H, 1H from NH); 7.10-7.20 (m, 3H, ArH), 8.80 + 8.95 (2s, 1H, Pyr-6H); 2.113 solid; m.p.: 168.2 C.; logp (HCOOH): 3,41; 1H-NMR (CDCl.sub.3, 400 MHZ, in ppm): 1.20 (d, 6H, 2*3H from CH(CH.sub.3).sub.2), 2.15 (m, 3H, 2H from CH.sub.2, 1H from CH.sub.2); ); 2.25 (m, 1H, 1H from CH.sub.2); 2.55 (m, 2H, 2H from CH.sub.2); 2.70-2.85 (m, 3H, 1H from CH.sub.2, 2H from CH.sub.2); 4.25 (m, 1H, 1H from CH.sub.2O); 4.30 (m, 1H, 1H from CH.sub.2O); 5.30 (br, 1H, CH); 5.90 (br, 1H, NH); 6.80 (m, 1H, ArH); 7,10 (m, 2H, ArH); 8.80 + 8.95 (2s, 1H, Pyr-6H); 2.114 oily; logp (HCOOH): 2.77; 1H-NMR (CDCl.sub.3, 400 MHZ, in ppm): 2.10 (m, 2H, 2H from CH.sub.2); 2.20 (m, 1H, 1H from CH.sub.2); 2.40 (m, 1H, 1H from CH.sub.2); 2.60 (m, 2H, 2H from CH.sub.2); 2.75-2.95 (m, 2H, 2*1H from CH.sub.2), 3.00-3.15 (m, 2H, 2*1H from CH.sub.2); 5.40 (br, 1H, 1H from CH), 5.90 und 6.15 (br, 1H, 1H from NH); 6.90 (m, 1H, ArH), 7.05 (m, 1H, ArH); 7.15 (m, 1H, ArH); 8.80 + 8.95 (2s, 1H, Pyr-6H); 2.115 oily; 2.116 solid; m.p.: 141.6 C.; logp (HCOOH): 2.90; 1H-NMR (CDCl.sub.3, 400 MHZ, in ppm): 1.40 und 1.45 (s, 2*3H, 2*3H from CH.sub.3), 1.80 ( m, 1H, 1H from CH.sub.2); 2.15 (m, 2H, 2H from CH.sub.2); 2.30 (m, 1H, 1H from CH.sub.2); 2.55 (m, 2H, 2H from CH.sub.2); 2.70-2.85 (m, 2H,.sub., 2H from CH.sub.2); 5.40 (br, 1H, CH); 5.60 (br, 1H, NH); 6.40 (m, 1H, ArH); 6.50 (m, 1H, ArH); 7.15 (m, 1H, ArH); 8.80 + 8.95 (2s, 1H, Pyr-6H); 2.117 oily; logp (HCOOH): 2.52; 1H-NMR (CDCl.sub.3, 400 MHZ, in ppm): 2.10 (m, 2H, 2H from CH.sub.2); 2.30 (s, 3H, 3H from CH.sub.3); 2.60 (m, 2H, 2H from CH.sub.2); 2.75-2.95 (m, 2H, 2*1H from CH.sub.2), 4.25 (m, 1H, 1H from CH.sub.2); 4.80 (m, 1H, 1H from CH.sub.2); 5.75 (br, 1H, 1H from CH), 5.80 (br, 1H, 1H from NH); 6.80 (m, 1H, ArH), 7.05 (m, 1H, ArH); 7.15 (m, 1H, ArH); 8.80 + 8.95 (2s, 1H, Pyr-6H); 2.118 oily; logp (HCOOH): 4.51; 1H-NMR (CDCl.sub.3, 400 MHZ, in ppm): 1.25 (d, 3H, 3H from CH.sub.3); 1.85-2.00 (m, 6H, 3*2H from CH.sub.2); 2.30 (s, m, 4H, 3H from CH.sub.3, 1H from CH.sub.2); 2.50 (m, 1H, 1H from CH.sub.2); 2.70 (s, 2H, 2H from CH.sub.2); 2.90 (2s, 2H, 2H from CH.sub.2); 3,05 (m, 1H, 1H from CH.sub.2), 5.40 (br, 1H, 1H from CH), 5.70 (br, 1H, 1H from NH); 7,00-7,15 (m, 3H, ArH), 8.80 + 8.95 (2s, 1H, Pyr-6H);

B. FORMULATION EXAMPLES

[0291] a) A dusting product is obtained by mixing 10 parts by weight of a compound of the formula (I) and/or salts thereof and 90 parts by weight of talc as an inert substance and comminuting the mixture in a hammer mill. [0292] b) A readily water-dispersible, wettable powder is obtained by mixing 25 parts by weight of a compound of the formula (I) and/or salts thereof, 64 parts by weight of kaolin-containing quartz as an inert substance, 10 parts by weight of potassium lignosulfonate and 1 part by weight of sodium oleoylmethyltaurate as a wetting agent and dispersant, and grinding the mixture in a pinned-disk mill. [0293] c) A readily water-dispersible dispersion concentrate is obtained by mixing parts by weight of a compound of the formula (I) and/or salts thereof with 6 parts by weight of alkylphenol polyglycol ether (Triton X 207), 3 parts by weight of isotridecanol polyglycol ether (8 EO) and 71 parts by weight of paraffinic mineral oil (boiling range for example about 255 to above 277 C.), and grinding the mixture in a friction ball mill to a fineness of below 5 microns. [0294] d) An emulsifiable concentrate is obtained from 15 parts by weight of a compound of the formula (I) and/or salts thereof, 75 parts by weight of cyclohexanone as a solvent and 10 parts by weight of ethoxylated nonylphenol as an emulsifier. [0295] e) Water-dispersible granules are obtained by mixing [0296] 75 parts by weight of a compound of the formula (I) and/or salts thereof, [0297] 10 parts by weight of calcium lignosulfonate, [0298] 5 parts by weight of sodium lauryl sulfate, [0299] 3 parts by weight of polyvinyl alcohol and [0300] 7 parts by weight of kaolin, [0301] grinding the mixture in a pinned-disk mill, and granulating the powder in a fluidized bed by spray application of water as a granulating liquid. [0302] f) Water-dispersible granules are also obtained by homogenizing and precomminuting, in a colloid mill, [0303] 25 parts by weight of a compound of the formula (I) and/or salts thereof, [0304] 5 parts by weight of sodium 2,2-dinaphthylmethane-6,6-disulfonate [0305] 2 parts by weight of sodium oleoylmethyltaurate, [0306] 1 part by weight of polyvinyl alcohol [0307] 17 parts by weight of calcium carbonate and [0308] 50 parts by weight of water, [0309] then grinding the mixture in a bead mill and atomizing and drying the resulting suspension in a spray tower by means of a one-phase nozzle.

C. BIOLOGICAL EXAMPLES

Test Description

1. Pre-Emergence Herbicidal Effect and Crop Plant Compatibility

[0310] Seeds of monocotyledonous and dicotyledonous weed plants and crop plants are laid out in wood-fiber pots in sandy loam and covered with soil. The compounds of the invention, formulated in the form of wettable powders (WP) or as emulsion concentrates (EC), are then applied to the surface of the covering soil as aqueous suspension or emulsion at a water application rate equating to 600 to 800 L/ha with addition of 0.2% wetting agent.

[0311] After the treatment, the pots are placed in a greenhouse and kept under good growth conditions for the trial plants. The damage to the trial plants is scored visually after a trial duration of 3 weeks by comparison with untreated controls (herbicidal activity in percent (%): 100% efficacy=the plants have died, 0% efficacy=like control plants).

[0312] In the tables below, the following abbreviations are used:

TABLE-US-00005 Crops: BRSNW: Brassica napus ORYSA: Oryza sativa TRZAS: Triticum aestivum (spring) ZEAMX: Zea mays

TABLE-US-00006 Undesired plants/weeds: ABUTH: Abutilon theophrasti ALOMY: Alopecurus myosuroides AMARE: Amaranthus retroflexus AVEFA: Avena fatua CYPES: Cyperus esculentus ECHCG: Echinochloa crus-galli LOLMU: Lolium multiflorum MATIN: Matricaria inodora PHBPU: Ipomoea purpurea POLCO: Polygonum convolvulus SETVI: Setaria viridis STEME: Stellaria media VERPE: Veronica persica VIOTR: Viola tricolor

TABLE-US-00007 TABLE 4 (pre-emergence efficacy): Ex. No Dosage Unit ORYSA TRZAS ZEAMX ALOMY AVEFA CYPES ECHCG LOLMU 1.3 320 g/ha 20 100 1.3 80 g/ha 20 20 20 80 1.4 320 g/ha 100 100 100 90 1.4 80 g/ha 100 100 80 1.7 320 g/ha 0 20 100 90 100 1.7 80 g/ha 0 0 80 1.8 320 g/ha 0 0 0 90 1.8 80 g/ha 0 0 0 1.10 320 g/ha 20 80 100 100 1.10 80 g/ha 0 0 100 1.20 1280 g/ha 0 1.20 320 g/ha 20 0 1.26 320 g/ha 0 90 80 100 100 1.26 80 g/ha 0 0 90 80 100 80 1.82 320 g/ha 3 0 1.82 80 g/ha 0 0 0 1.83 1280 g/ha 100 90 100 100 1.85 320 g/ha 80 100 90 90 1.85 80 g/ha 90 1.86 320 g/ha 10 10 0 100 1.86 80 g/ha 0 0 0 1.87 320 g/ha 0 10 100 1.87 80 g/ha 0 0 0 1.88 320 g/ha 0 0 1.88 80 g/ha 0 0 0 1.89 320 g/ha 0 0 0 1.89 80 g/ha 0 0 1.90 1280 g/ha 20 0 20 100 80 1.90 320 g/ha 20 0 20 1.92 320 g/ha 0 0 20 1.92 80 g/ha 0 20 2.13 320 g/ha 10 100 90 100 100 100 2.13 80 g/ha 0 0 100 100 2.19 320 g/ha 0 10 100 90 100 100 2.23 320 g/ha 100 90 90 100 100 2.23 80 g/ha 5 0 0 80 80 80 2.25 320 g/ha 0 0 100 2.25 80 g/ha 0 0 0 2.26 320 g/ha 90 90 100 100 2.26 80 g/ha 0 0 80 2.43 320 g/ha 100 100 80 100 100 2.43 80 g/ha 0 20 100 100 100 2.44 320 g/ha 100 80 100 100 2.44 80 g/ha 20 10 80 0 90 100 2.45 320 g/ha 10 90 80 100 100 2.45 80 g/ha 0 10 100 80 2.46 320 g/ha 0 0 90 100 100 2.46 80 g/ha 0 0 90 90 100 2.50 1280 g/ha 0 2.50 320 g/ha 0 2.52 320 g/ha 20 30 10 100 90 2.52 80 g/ha 0 0 0 2.91 320 g/ha 20 20 90 80 100 100 2.92 320 g/ha 20 20 20 100 2.92 80 g/ha 0 0 0 2.93 1280 g/ha 20 0 0 100 2.94 320 g/ha 0 0 0 80 100 90 2.95 80 g/ha 0 0 2.95 320 g/ha 0 0 0 80 2.95 80 g/ha 0 0 0 2.96 320 g/ha 0 0 10 80 100 90 2.96 80 g/ha 0 0 2.97 320 g/ha 20 100 100 100 100 2.97 80 g/ha 10 0 100 100 2.99 320 g/ha 10 20 10 80 100 80 2.99 80 g/ha 0 10 0 2.100 320 g/ha 10 10 80 100 100 2.100 80 g/ha 0 0 100 2.101 320 g/ha 0 10 80 100 100 2.101 80 g/ha 0 10 2.102 320 g/ha 0 0 0 100 100 100 2.102 80 g/ha 0 0 0 2.103 320 g/ha 0 0 0 80 100 90 2.103 80 g/ha 0 0 0 90 2.104 320 g/ha 20 0 90 2.104 80 g/ha 20 0 0 2.117 320 g/ha 0 0 20 2.118 320 g/ha 10 0 90 100 100 2.118 80 g/ha 10 0 0 80 Ex. No SETVI ABUTH AMARE MATIN PHBPU POLCO STEME VERPE VIOTR 1.3 80 100 100 100 90 100 1.3 100 90 80 100 1.4 90 100 100 100 100 100 100 100 1.4 100 100 100 90 100 100 1.7 90 100 100 100 90 100 100 100 1.7 90 80 100 1.8 80 100 100 100 100 1.8 100 1.10 100 80 100 100 100 100 100 1.10 100 100 100 100 100 100 1.20 100 100 100 100 100 100 1.20 90 90 100 100 90 1.26 100 100 100 100 100 100 100 1.26 100 100 100 100 100 100 100 1.82 90 90 80 100 100 100 1.82 90 90 100 100 1.83 100 100 100 100 100 100 100 100 100 1.85 90 100 90 80 100 100 100 1.85 80 80 100 100 100 1.86 100 100 100 100 100 100 1.86 100 100 80 1.87 100 100 100 100 100 100 1.87 80 90 100 1.88 100 100 100 100 90 1.88 80 100 100 1.89 100 100 80 100 100 1.89 100 80 80 90 1.90 100 100 90 100 100 100 1.90 90 100 80 100 1.92 100 100 100 100 1.92 100 100 2.13 100 100 100 100 100 100 2.13 100 100 100 100 100 100 100 2.19 100 100 100 100 100 100 100 2.23 100 100 100 100 100 100 100 2.23 100 100 100 100 100 100 100 2.25 100 100 100 100 100 100 100 2.25 90 90 100 100 100 2.26 90 100 100 100 100 100 100 2.26 100 100 80 90 2.43 100 100 100 100 100 100 100 100 2.43 90 100 100 100 100 100 100 2.44 100 100 100 100 100 100 100 2.44 100 100 90 90 100 100 100 2.45 100 80 100 90 90 100 100 100 100 2.45 100 80 100 90 100 100 100 100 2.46 90 80 100 100 100 100 100 100 2.46 90 90 90 100 100 100 2.50 80 100 100 100 90 2.50 100 100 90 2.52 70 0 100 100 60 100 100 100 2.52 90 100 2.91 100 100 100 100 100 80 100 100 100 2.92 100 100 90 100 100 100 2.92 80 100 100 90 2.93 80 90 100 100 80 2.94 90 100 100 100 100 100 100 2.95 100 90 100 100 90 2.95 100 90 100 100 100 2.95 90 100 100 100 2.96 90 100 90 80 100 100 100 2.96 100 100 100 100 2.97 100 100 100 100 100 100 100 2.97 100 100 100 100 100 100 100 2.99 100 100 100 100 100 100 100 2.99 90 90 90 100 100 2.100 100 90 100 100 90 100 100 100 2.100 100 100 100 90 100 100 100 2.101 100 100 100 100 100 100 100 2.101 100 100 100 100 100 100 2.102 100 100 100 90 100 100 100 2.102 100 80 90 100 100 100 2.103 100 100 100 100 100 2.103 100 100 100 100 2.104 100 100 100 100 100 100 100 2.104 80 100 100 90 2.117 80 100 2.118 100 100 100 100 100 100 100 2.118 100 100 90 100 100 100

[0313] As shown by the results, the compounds of the invention have good herbicidal pre-emergence activity against a broad spectrum of weed grasses and broad-leaved weeds. For example, the compounds from table 1 have very good herbicidal activity against harmful plants such as Avena fatua, Stellaria media, Echinochloa crus-galli, Lolium multiflorum, Setaria viridis, Abutilon theophrasti, Amaranthus retroflexus and Alopecurus myosuroides when applied by the pre-emergence method at an application rate of 1.28 kg or less of active substance per hectare. The compounds of the invention are therefore suitable for control of unwanted plant growth by the pre-emergence method.

2. Post-Emergence Herbicidal Effect and Crop Plant Compatibility

[0314] Seeds of monocotyledonous and dicotyledonous weed and crop plants are laid out in sandy loam in wood-fiber pots, covered with soil and cultivated in a greenhouse under good growth conditions. 2 to 3 weeks after sowing, the test plants are treated at the one-leaf stage. The compounds of the invention, formulated in the form of wettable powders (WP) or as emulsion concentrates (EC), are then sprayed onto the green parts of the plants as aqueous suspension or emulsion at a water application rate equating to 600 to 800 L/ha with addition of 0.2% wetting agent. After the trial plants have been left to stand in a greenhouse under optimal growth conditions for about 3 weeks, the efficacy of the formulations is scored visually in comparison to untreated controls (herbicidal action in percent (%): 100% efficacy=the plants have died, 0% efficacy=like control plants).

TABLE-US-00008 TABLE 5 (post-emergence efficacy): Ex. No Dosage Unit ORYSA TRZAS ZEAMX BRSNW ALOMY AVEFA ECHCG LOLMU 1.10 320 g/ha 90 1.10 80 g/ha 20 1.26 320 g/ha 0 0 90 80 100 80 1.26 80 g/ha 0 0 0 90 1.82 320 g/ha 0 1.85 320 g/ha 20 20 20 90 1.85 80 g/ha 20 10 0 1.86 320 g/ha 0 0 0 1.86 80 g/ha 0 0 0 1.88 320 g/ha 0 20 10 1.88 80 g/ha 0 0 0 2.13 320 g/ha 0 20 90 100 2.13 80 g/ha 0 10 10 90 2.19 320 g/ha 20 20 100 100 2.23 320 g/ha 20 0 100 90 100 2.23 80 g/ha 20 0 0 2.25 320 g/ha 0 20 0 2.25 80 g/ha 0 10 0 2.26 320 g/ha 0 0 0 2.26 80 g/ha 0 0 0 20 2.43 320 g/ha 10 100 90 100 2.43 80 g/ha 10 10 0 90 80 2.44 320 g/ha 0 0 90 100 2.44 80 g/ha 0 0 10 100 2.45 320 g/ha 10 0 80 80 100 100 2.45 80 g/ha 20 10 0 100 2.46 320 g/ha 20 10 0 100 100 2.46 80 g/ha 10 10 0 80 2.52 320 g/ha 0 0 0 2.52 80 g/ha 0 0 0 20 2.91 320 g/ha 0 100 100 2.92 320 g/ha 0 10 0 2.92 80 g/ha 0 0 0 2.94 320 g/ha 0 20 0 2.94 80 g/ha 0 10 0 2.96 320 g/ha 0 20 10 2.96 80 g/ha 0 10 0 2.97 320 g/ha 0 100 100 100 2.97 80 g/ha 0 90 2.99 320 g/ha 0 0 0 80 100 90 2.99 80 g/ha 0 0 0 2.100 320 g/ha 0 20 10 100 100 2.100 80 g/ha 0 10 10 100 2.101 320 g/ha 0 0 0 100 100 2.101 80 g/ha 0 0 0 2.102 320 g/ha 0 0 100 2.102 80 g/ha 0 20 0 2.103 320 g/ha 0 20 0 80 2.103 80 g/ha 0 10 0 2.104 320 g/ha 0 0 0 2.104 80 g/ha 0 0 0 2.118 320 g/ha 0 10 100 80 2.118 80 g/ha 0 0 0 Ex. No SETVI ABUTH AMARE MATIN PHBPU POLCO STEME VERPE VIOTR 1.10 80 90 90 90 80 100 1.10 80 80 90 1.26 90 100 90 90 90 90 1.26 80 90 90 90 1.82 90 1.85 100 80 100 80 1.85 90 90 80 1.86 90 100 100 100 90 1.86 90 100 90 90 1.88 80 100 1.88 90 2.13 100 90 90 100 100 90 90 2.13 90 100 80 2.19 100 100 80 90 100 90 80 2.23 80 100 80 100 100 2.23 80 2.25 100 90 80 100 90 80 2.25 90 90 90 2.26 80 80 90 80 2.26 80 80 90 2.43 80 80 100 80 90 100 100 90 2.43 90 80 90 100 90 2.44 80 100 100 90 100 100 2.44 90 100 90 80 90 2.45 90 100 100 90 100 80 100 100 100 2.45 100 100 90 100 80 90 90 100 2.46 80 100 90 100 90 100 2.46 80 90 100 80 100 2.52 100 80 2.52 100 80 2.91 90 100 100 100 80 100 100 90 2.92 90 80 90 90 2.92 80 80 90 90 2.94 90 80 90 90 100 2.94 90 90 2.96 80 80 100 90 90 2.96 100 90 80 2.97 80 80 100 80 100 90 100 100 100 2.97 80 100 80 80 100 90 2.99 100 100 80 100 90 100 2.99 90 100 80 90 100 2.100 90 100 90 80 100 90 2.100 90 80 100 90 2.101 100 80 80 100 80 2.101 100 100 2.102 100 100 100 100 2.102 80 90 90 80 2.103 100 100 100 80 2.103 80 100 80 80 2.104 80 80 100 100 2.104 80 80 90 90 2.118 80 100 100 90 100 90 100 2.118 90 80 90 100

[0315] As the results show, inventive compounds have good herbicidal post-emergence efficacy against a broad spectrum of weed grasses and broad-leaved weeds. For example, the compounds from table 2 have very good herbicidal activity against harmful plants such as Avena fatua, Stellaria media, Echinochloa crus-galli, Lolium multiflorum, Setaria viridis, Abutilon theophrasti, Amaranthus retroflexus and Alopecurus myosuroides when applied by the post-emergence method at an application rate of 1.28 kg or less of active substance per hectare. The compounds of the invention are therefore suitable for control of unwanted plant growth by the post-emergence method.