CA2386800A1

CA2386800A1 - Alkylamino-1,3,5-triazines, process for their preparation and their use as herbicides and plant growth regulators

Info

Publication number: CA2386800A1
Application number: CA002386800A
Authority: CA
Inventors: Hartmut Ahrens; Lothar Willms; Klemens Minn; Jurgen Zindel; Jens Hollander; Wolfgang Giencke; Klaus Lorenz; Hermann Bieringer; Thomas Auler; Felix Thurwachter
Original assignee: Individual
Current assignee: Bayer CropScience AG
Priority date: 1999-10-08
Filing date: 2000-09-27
Publication date: 2001-04-19
Also published as: CO5231183A1; EP1222178A1; DE19948450A1; WO2001027093A1; BR0014853A; AU7422100A; AR025963A1

Abstract

The invention relates to alkyl-amino-1,3,5-triazines, to a method for producing them and to their use as herbicides and as plant growth regulators.
Compounds of formula (I), wherein R1, R2, R3, R4, R5, R6, R7, R8 and A have the meanings given in claim n~1, and their salts are suitable for use as herbicides and plant growth regulators. Said compounds of formula (I) are produced according to the method provided in claim n~8.

Description

Alkylamino-1,3,5-triazines, process for their preparation and their use as herbicides and plant growth regulators The invention relates to the technical field of crop protection agents, such as herbicides and plant growth regulators, in particular herbicides for the selective control of harmful plants in crops of useful plants.
It is known that 4-amino-2-[N-(1-arylalkyl)amino]-1,3,5-triazines which are optionally substituted in the 6 position on the triazine ring by optionally halogenated hydrocarbon "" groups or other groups, and their derivatives, have herbicidal and plant-growth-regulating properties; cf., for example, US-A-3816419, US-A-5290754 (WO-A-90/9378, EP-A-0411153), W095/06642, WO-A-97/31904, W098/15536, W098I42684, WO-A-99/18100, WO-A-99/19309, WO-A-99/37627, W099/46249, JP-A-62,298,577, JP-A-62,294,669, EP-A-0191496 and literature cited therein.
Some of the known active compounds have, when used, disadvantages, such as insufficient herbicidal activity against harmful plants, too limited a spectrum of harmful plants which can be controlled with an active compound, or insufficient selectivity in crops of useful plants. Other active compounds cannot be prepared economically on an industrial scale, owing to reagents or precursors which are difficult to obtain, or they have insufficient chemical stability.
It is therefore desirable to provide alternative active compounds which can, if appropriate, advantageously, be employed as herbicides or plant-growth regulators.
The present invention provides compounds of the formula (I) and salts thereof R~

N ~ N R3 R6 (I) A N N
R2 R8 R~
in which A a group of the formula NRaRb, in which Ra and Rb, independently of one another, are hydrogen, formyl or else aminocarbonyl or else amino(thiocarbonyl) or (C~-C~p)alkyl, (C2-C~Q)alkenyl, (C2-C~p)alkynyl, (C~-C~p)alkylsulfinyl, (C~-C~p)alkyl-sulfonyl, (C~-C~p)alkoxy, [(C~-C~p)alkyl]carbonyl, [(C~-C~p)alkoxy]-carbonyl or else N-mono[(C~-C~p)alkyl]aminocarbonyl or else N,N-di[(C~-C~p)alkyl]aminocarbonyl or else [(C~-C~p)alkylthio]carbonyl or else [(C~-C~p)alkyl](thiocarbonyl) or else [(C~-C~p)alkoxy] (thiocarbonyl) or else N-mono[(C~-C~p)alkyl]amino(thiocarbonyl) or else N,N-di[(C~-C~0)-alkyl]amino(thiocarbonyl) or else [(C~-C~p)alkylthio](thiocarbonyl), where ,,., each of the 16 last-mentioned radicals is unsubstituted or substituted, preferably unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C~-C4)alkoxy, (C~-Cq.)haloalkoxy, (C~-C4)hydroxyalkoxy and (C~-Cq,)alkoxy-(C~-Cq.)alkoxy, or are (C3-Cg)cycloalkyl, (C5-Cg)cycloalkenyl, (C3-Cg)cycloalkoxy, (C5-Cg)cycloalkenyloxy, phenyl, phenoxy, phenylamino, phenylcarbonyl or else naphthylcarbonyl or phenylsulfonyl, heterocyclyl, heterocyclyloxy, heterocyclylamino, heterocyclylcarbonyl or heterocyclylsulfonyl, where each of the 15 last-mentioned radicals is unsubstituted or substituted, preferably unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, cyano, hydroxyl, (C~-C4)alkyl, (C~-C4)haloalkyl, (C~-C4)hydroxyalkyl, (C~-C4)alkoxy-(C~-C4)alkyl, (C~-C4)alkoxy, (C~-C4)haloalkoxy, (C~-C4)hydroxyalkoxy and (C1-C4)alkoxy-(C1-C4)alkoxy and heterocyclyl in the radicals mentioned is in each case heterocyclyl having 3 to 9 ring atoms, 1 to 4 of which are hetero ring atoms selected from the group consisting of N, O and S, or one of the radicals Ra and Rb is as defined above and the other of the radicals Ra and Rb is a group of the formula NR'R", where R' and R", independently of one another, are H or (C~-C6)alkyl which is .~ unsubstituted or substituted, preferably unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, hydroxyl, (C~-C4)alkoxy, (C1-C4)haloalkoxy, (C1-C4)hydroxyalkoxy and (C1-C4)alkoxy-(C1-C4)alkoxy, or R' and R" together are straight-chain (C2-C5)alkylene which is unsubstituted or substituted by one or more radicals selected from the group consisting of (C~-C4)alkyl, (C~-C4)alkoxy and (C1-C4)alkoxy-(C~-C4)alkyl, or Ra and Rb together are (C~-C~p)alkylidene which is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, ,,.~, cyano, (Ct-C4)alkoxy, (C~-C4)haloalkoxy and (Ct-C4)alkylthio, or NRaRb together are a heterocyclyl radical which is attached to the nitrogen atom and has 3 to 6 ring atoms and, in addition to the nitrogen atom as hetero ring atom, optionally contains 1 to 3 further hetero ring atoms selected from the group consisting of N, O and S, where the heterocycle is unsubstituted or substituted, preferably unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, cyano, hydroxyl, (C~-C4)alkyl, (C~-C4)haloalkyl, (C1-C4)hydroxyalkyl, (C~-C4)alkoxy, (C~-C4)haloalkoxy, (C~-C4)hydroxyalkoxy, (C~-C4)alkoxy-(C~-C4)alkoxy, (C~-C4)alkoxy-(C~-C4)alkyl and oxo, or A is (C1-Cg)alkyl, (C2-Cg)alkenyl, (C2-Cg)alkynyl, (Cg-Cs)cycloalkyl or (C5-Cg)cycloalkenyl, where each of the 5 last-mentioned radicals is unsubstituted or substituted, preferably unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C~-C4)alkoxy, (Ct-C4)haloalkoxy, (C~-C4)alkylthio, (C1-C4)alkoxy-(C~-C4)alkoxy and, in the case of cyclic radicals, also (C~-C4)alkyl, (C1-C4)haloalkyl and (C~-C4)alkoxy-(C~-C4)alkyl, and R~ is hydroxyl, or (C~-C~p)alkyl, which is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, hydroxyl, cyano, nitro, thiocyanato, formyl, amino, (C1-C4)alkoxy, (C~-C4)haloalkoxy, (C2-C4)alkenyloxy, (C2-C4)haloalkenyloxy, (C2-C4)alkynyloxy, (C2-C4)haloalkynyloxy, N-mono(C~-C4)alkylamino, N,N-di(C1-C4)alkylamino, (C~-C4)alkylthio, (C1-C4)alkylsulfinyl, (C~-C4)haloalkylsulfinyl, (C~-C4)alkylsulfonyl, (C~-C4)haloalkylsulfonyl, [(C~-C4)alkyl]carbonyl, [(C~-C4)haloalkyl]carbonyl, [(C~-C4)alkoxy]carbonyl, (C3-C9)cycloalkyl, (C5-Cg)cycloalkenyl, phenyl and heterocyclyl, where each of the 4 last-mentioned radicals is unsubstituted or '"'~ substituted, preferably unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, cyano, hydroxyl, (C~-C4)alkyl, (C~-C4)haloalkyl, (C2-C4)alkenyl, (C2-C4)haloalkenyl, (C2-C4)alkynyl, (C2-C4)haloalkynyl, (Ct-C4)alkoxy, (C~-C4)haloalkoxy and (Ct-C4)alkylthio, and heterocyclyl in the 5 last-mentioned radicals contains in each case 3 to 9 ring atoms, 1 to 4 of which are hetero ring atoms selected from the group consisting of N, O and S, or is [(C~-Cg)alkyl]carbonyl, [(C~-Cg)alkoxy]carbonyl, (C~-Cg)alkylsulfinyl or (C1-C4)alkylsulfonyl, where each of the 4 last-mentioned radicals is unsubstituted or substituted, preferably unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C1-C4)alkoxy, (C~-C4)haloalkoxy and (C1-C4)alkylthio, or is (C3-Cg)cycloalkyl, which is unsubstituted or substituted, (Cs-Cs)cycloalkenyl, which is unsubstituted or substituted, where preferably each of the two last-5 mentioned cyclic radicals is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, cyano, (C~-C4)alkyl, (C1-C4)haloalkyl, (C2-C4)alkenyl, (C2-C4)alkynyl, (Ct-C4)alkoxy, (C~-C4)haloalkoxy and (C1-C4)alkylthio, ~"" where the radical Rt , including substituents, preferably has 1 to 30 cartaon atoms, in particular 1 to 20 carbon atoms, R2 is H or formyl, (C1-C~p)alkyl, (C2-C~p)alkenyl, (C2-C~p)alkynyl, (C1-C~p)alkylsulfinyl, (C~-C~p)alkylsulfonyl, (Ct-C~p)alkoxy, [(C~-C~p)alkyl]carbonyl, [(C~-C~p)alkoxy]carbonyl, where each of the 8 last-mentioned radicals is unsubstituted or substituted, preferably unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (Ct-C4)alkoxy, (C~-C4)haloalkoxy and (Ct-C4)hydroxyalkoxy and also (C~-C4)alkoxy-(C1-C4)alkoxy, or ,,~.. is (Cg-C6)cycloalkyl, (C5-Cs)cycloalkenyl, (C3-C6)cycloalkoxy, (C5-Cg)cycloalkenyloxy, phenyl, phenoxy, phenylamino, phenylcarbonyl, phenylsulfonyl, heterocyclyl, heterocyclyloxy, heterocyclylamino, heterocyclylcarbonyl or heterocyclylsulfonyl, where each of the 14 last-mentioned radicals is unsubstituted or substituted and heterocyclyl in the 5 last-mentioned radicals preferably contains in each case 3 to 9 ring atoms, 1 to 4 of which are hetero ring atoms selected from the group consisting of N, O and S, where preferably each of the 14 radicals mentioned is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, cyano, hydroxyl, (C~-C4)alkyl, (C~-C4)haloalkyl, (C~-C4)hydroxyalkyl, (C~-C4)alkoxy, (C~-C4)haloalkoxy and (C~-C4)hydroxyalkoxy and also (C~-C4)alkoxy-(C~-C4)alkoxy, or is a group of the formula NR°Rd, where R° and Rd, independently of one another, are H, formyl, (C~-Cg)alkyl, (C2-C6)alkenyl, (C2-Cg)alkynyl, (C~-Cg)alkylsulfinyl, (C~-Cg)alkylsulfonyl, (C~-Cg)alkoxy, [(C~-Cg)alkyl]carbonyl or [(C~-Cg)alkoxy]carbonyl, where each of the 8 last-mentioned groups is unsubstituted or substituted, preferably unsubstituted or substituted by one or more radicals selected from the group consisting halogen, hydroxyl, (C~-C4)alkoxy, (C~-C4)haloalkoxy, (C~-C4)hydroxyalkoxy and (C~-C4)alkoxy-(C~-C4)alkoxy, or R~ and Rd together are straight-chain (C2-C5)alkylene, which is unsubstituted or substituted by one or more radicals selected from the group consisting of (C~-C4)alkyl, (C~-C4)alkoxy, (C~-C4)alkoxy-(C~-C4)alkyl and oxo, R3 is halogen, CN, N02, SCN or a radical of the formula -X~-A~, where X~ is a direct bond or a divalent group of the formula -O-, -S(O)p-, -S(O)p-O-, -O-S(O)p-, -CO-, -O-CO-, -CO-O-, -S-CO-, -CO-S-, -S-CS-, -CS-S-, -O-CO-O-, -NR~ -, -O-NR~-, -NR~-O-, -NR~-CO-, -CO-NR~-, -O-CO-NR~- or -NR~-CO-O-, in which in each case p is the integer 0, 1 '""~ or 2 and R~ is hydrogen, (C~-Cg)alkyl, (C2-Cg)alkenyl, (C2-Cg)alkynyl, phenyl, phenyl-(C~-Cg)alkyl, (C3-Cg)cycloalkyl or [(C~-Cg)alkyl]carbonyl, and A~ is hydrogen, (C~-C~p)alkyl, (C2-C~p)alkenyl, (C2-C~p)alkynyl, (C3-Cg)cycloalkyl, (C5-Cg)cycloalkenyl, phenyl or heterocyclyl having 3 to 9 ring atoms and 1 to 4 hetero ring atoms selected from the group consisting of N, O and S, where each of the 7 last-mentioned radicals is unsubstituted or substituted, preferably unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, cyano, hydroxyl, (C~-C4)alkyl, (C3-Cg)cycloalkyl, (C~-C4)alkoxy, (C~-C4)haloalkoxy and (C~-C4)hydroxyalkoxy and, in the case of cyclic radicals, also (C~-C4)haloalkyl, (C~-C4)alkoxy-(C~-C4)alkyl and (C~-C4)hydroxyalkyl and, including substituents, has preferably up to 20 carbon atoms, each of the radicals R4, R5, R6, R' and R8, independently of one another, is halogen, nitro, cyano, thiocyanato or a radical of the formula -X2-A2, where X2 is a direct bond or a divalent group of the formula -O-, -S(O)q-, -S(O)q-O-, -O -S(O)q-, -S(O)q-NR'-, -NR'-S(O)q-, -CO-, -O-CO-, -CO-O-, -S-CO-, -CO-S-, -S-CS-, -CS-S-, -O-CO-O-, -NR' -, -O-NR'-, -NR'-O-, -NR'-CO-, -CO-NR'-, -O-CO-NR'- or -NR'-CO-O-, in which in each case q is the integer 0, 1 or 2 and R' is hydrogen, amino, substituted amino, (C~-Cg)alkyl, (C2-Cg)alkenyl, (C2-Cg)alkynyl, phenyl, phenyl-(C~-Cg)alkyl, phenylcarbonyl, (C3-Cg)cycloalkyl, (C5-Cg)cycloalkenyl, [(C~-Cg)alkyl]carbonyl, (C~-Cg)alkylsulfonyl, (C~-Cg)alkylsulfinyl, phenylsulfonyl or phenylsulfinyl, where each of the 13 last-mentioned radicals is unsubstituted or substituted, preferably unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, cyano, hydroxyl, (C~-C4)alkyl, (C~-C4)alkoxy, (C~-C4)haloalkoxy and (C~-C4)hydroxyalkoxy and, in the case of cyclic "~ radicals, also (C~-C4)haloalkyl, (C~-C4)alkoxy-(C~-C4)alkyl and (C~-C4)hydroxyalkyl, and A2 is hydrogen, (C~-C~p)alkyl, (C2-C~p)alkenyl, (C2-C~p)alkynyl, (C3-Cg)cycloalkyl, (C~-Cg)cycloalkenyl, phenyl or heterocyclyl, where each of the 7 last-mentioned radicals is unsubstituted or substituted, preferably unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, cyano, hydroxyl, amino, mercapto, aminocarbonyl, mono- and di(C~-Cg)alkylamino, mono- and diarylamino, N-(C~-Cg)alkyl-N-arylamino, mono- and diacylamino, N-(C~-Cg)alkyl-N-acylamino, N-aryl-N-acylamino, (C~-Cg)alkoxy, (C~-Cg)alkylthio, (C~-Cg)alkylsulfonyl, (C~-Cg)alkylsulfinyl, [(C~-C5)alkyl]carbonyl, [(C~-C5)alkoxy]carbonyl, [(C~-Cg)alkyl]carbonyloxy, (Cg-Cg)cycloalkyl, (Cg-Cg)cycloalkoxy, (C3-Cg)cycloalkylcarbonyl, (C3-Cg)cycloalkylcarbonyloxy, phenyl, phenoxy, phenylthio, phenylcarbonyl, phenylcarbonyloxy, heterocyclyl, heterocyclyloxy, heterocyclylthio, heterocyclylcarbonyl, heterocycly~arbonyloxy and, in the case of cyclic radicals, also (C~-Cg)alkyl, where each of the 31 last-mentioned radicals is unsubstituted or substituted, preferably unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, cyano, hydroxyl, amino, mono- and di(C~-Cg)alkylamino, mono- and di-arylamino, N-(C~-Cg)alkyl-N-arylamino, mono- and di-(C~-Cg)acylamino, N-(Ct-Cg)alkyl-N-acylamino, (C~-Cg)alkoxy, (C~-Cg)alkylthio, (Cg-Cg)cycloalkyl, (Cg-Cg)cycloalkoxy, phenyl, phenoxy and phenylthio and, in the case of cyclic radicals, also (C1-Cg)alkyl, (C1-C6)haloalkyl and (C~-C4)alkoxy-(C1-Cs)alkyl and where heterocyclyl in A2 in each case contains 3 to 9 ring atoms and 1 to 4 hetero ring atoms selected from the group consisting of '"~"' N, O and S, and where A2, including substituents, has preferably up to 20 carbon atoms, or two adjacent radicals from the group consisting of R4, R5, R6, R' and Rg together with the carbon atoms of the phenyl ring to which they are attached form a fused ring having 4 to 6 ring atoms which is carbocyclic or contains 1 to 3 hetero ring atoms from the group consisting of N, O and S and which is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C1-C6)alkyl, iC~-Cg)haloalkyl, (C2-Cg)alkenyl, (C2-Cg)alkynyl, (C~-Cg)alkoxy, [(C~-Cg)haloalkoxy, (C1-Cg)alkyl]carbonyl, [(C1-Cg)alkoxyJcarbonyl, (C~-Cg)alkylsulfonyl and (C1-Cg)alkylsulfinyl, where at least two radicals, preferably 2 or 3 radicals, in particular 2 radicals, selected from the group consisting of R4, R5, R6, R' and R$ are different from hydrogen, except for compounds of the formula (I) and salts thereof in which A is NH2, R1 is a radical of the formula -C(CH3)(X*)(R*), in which X* = halogen and R* =
H, CHg or C2H5, R2 is H, R3 is CHg, R5 is CH3 or OCH3, R6 is CH3 or OCH3 and R4, R' and Re are each H.
The last-mentioned compounds (I), which are excluded, are already known from US-A-5290754 (VIIO-A-90/9378, EP-A-0411153).
Unless defined otherwise, divalent radicals, for example X~ - -CO-NR~-, are defined such that in the composed groups, for example -X1-A~, the bond of the divalent radical linked to the group A~ is the bond which is written on the right in the formula for the divalent radical, i.e. -X~-A1 is a group of the formula -CO-NR~-A1; this applies correspondingly to analogous divalent radicals.
The invention also provides all stereoisomers which are embraced by the formula (I), and mixtures thereof. Such compounds of the formula (I) contain one or more asymmetrically substituted carbon atoms or else double bonds, which are not specifically mentioned in the general formulae (I). The possible stereoisomers, which are defined by their specific steric form, such as enantiomers, diastereomers, including Z and E isomers, are all embraced by the formula (I) and can be obtained by customary methods from mixtures of the stereoisomers or else be prepared by stereoselective reactions in combination with the use of stereochemically pure or enriched starting materials. Of particular interest are also the stereoisomers which 5 result from the asymmetrically substituted carbon atom to which the group R3 is attached, if R3 is not hydrogen. The isomers which are R- and S-configured at this center, which represent enantiomers, if no further asymmetrically substituted carbon atom is present in the molecule of the formula (I), therefore also form part of the subject matter of the invention. In general, the biological activities of these R and S
10 isomers are not identical, but in the individual case, depending on the species of harmful plant and the crop, one of the isomers has a higher herbicidal action or selectivity.
If compounds of the formula (I) are also capable of forming tautomers whose structure is formally not represented or included in the formula (1), these tautomers are nevertheless embraced by the definition of the compounds of the formula (I) according to the invention.
The compounds of the formula (I) can form salts by addition of a suitable inorganic or organic acid, such as, for example, HCI, HBr, H2S04 or HN03, but also oxalic acid or sulfonic acids, to a basic group, such as, for example, amino or alkylamino.
Suitable substituents which are present in deprotonated form, such as, for example, sulfonic acids or carboxylic acids, can form inner salts with groups which for their part can be protonated, such as amino groups. Salts can also be formed by replacing the hydrogen of suitable substituents, such as, for example, sulfonic acids or carboxylic acids, by an agriculturally suitable cation. These salts are, for example, metal salts, in particular alkali metal salts or alkaline earth metal salts, in particular sodium salts and potassium salts, or else ammonium salts or salts with organic amines.
In the formula (I) and all the formulae hereinbelow, the radicals alkyl, alkoxy, haloalkyl, haloalkoxy, alkylamino and alkylthio and the corresponding unsaturated and/or substituted radicals can in each case be straight-chain or branched in the carbon skeleton. Unless specifically mentioned otherwise, the lower carbon skeletons, for example with 1 to 6 carbon atoms or in the case of unsaturated groups with 2 to 6 carbon atoms are preferred for these radicals. Alkyl radicals, also in the composed meanings, such as alkoxy, haloalkyl, and the like, are, for example, methyl, ethyl, n- or isopropyl, n-, i-, t- or 2-butyl, pentyls, hexyls, such as n-hexyl, isohexyl and 1,3-dimethylbutyl, heptyls, such as n-heptyl, 1-methylhexyl and 1,4-dimethylpentyl;
alkenyl and alkynyl radicals have the meaning of the possible unsaturated radicals which correspond to the alkyl radicals; alkenyl is, for example, allyl, 1-methylprop-2-en-1-yl, 2-methylprop-2-en-1-yl, but-2-en-1-yl, but-3-en-1-yl, 1-methyl-but-3-en-1-yl and 1-methyl-but-2-en-1-yl; alkynyl is, for example, propargyl, but-2-yn-1-yl, but-3-yn-1-yl, 1-methylbut-3-yn-1-yl.
Alkylidene, for example in the form (C~-C~p)alkylidene, is the radical of a straight-chain or branched alkane which is attached via a double bond, the position of the binding site not yet being fixed. In the case of a branched alkane, the only possible positions are, of course, those where two hydrogen atoms can be replaced by the double bond;
examples of radicals are =CH2, =CH-CH3, =C(CH3)-CHg, =C(CH3)-C2H5 or =C(C2H5)-C2H5.
Cycloalkyl is a carbocyclic saturated ring system having preferably 3-8 carbon atoms, for example cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl. In the case of substituted cycloalkyl, this includes cyclic systems with substituents, where the A.., substitutents are attached to the cycloalkyl radical via a double bond, for example an alkylidene group such as methylidene. Substituted cycloalkyl also includes polycyclic aliphatic systems, such as, for example, bicyclo[1.1.0]butan-1-yl, bicyclo[1.1.0]butan-2-y1, bicyclo[2.1.0]pentan-1-yl, bicyclo[2.1.0]pentan-2-yl, bicyclo[2.1.0]pentan-5-yl, adamantan-1-yl and adamantan-2-yl.
Cycloalkenyl is a carbocyclic non-aromatic, partially unsaturated ring system having preferably 4-8 carbon atoms, for example 1-cyclobutenyl, 2-cyclobutenyl, 1-cyclopentenyl, 2-cyclopentenyl, 3-cyclopentenyl, or 1-cyclohexenyl, 2-cyclohexenyl, 3-cyclohexenyl, 1,3-cyclohexadienyl or 1,4-cyclohexadienyl. For substituted cycloalkenyl, the illustrations for substituted cycloalkyl apply correspondingly.

Halogen is, for example, fluorine, chlorine, bromine or iodine. Haloalkyl, -alkenyl and -alkynyl are alkyl, alkenyl and alkynyl, respectively, which are partially or fully substituted by halogen, preferably by fluorine, chlorine and/or bromine, in particular by fluorine or chlorine, for example, monohaloalkyl, perhaloalkyl, CFg, CHF2, CH2F, CF3CF2, CH2FCHC1, CCIg, CHCI2, CH2CH2C1; haloalkoxy is, for example, OCFg, OCHF2, OCH2F, CF3CF20, OCH2CF3 and OCH2CH2CI; this applies correspondingly to haloalkenyl and other halogen-substituted radicals.
Aryl is a mono-, bi- or polycyclic aromatic system, for example phenyl, naphthyl, ",~"10 tetrahydronaphthyl, indenyl, indanyl, pentalenyl, fluorenyl and the like, preferably phenyl.
A heterocyclic radical or ring (heterocyclyi) can be saturated, unsaturated or heteroaromatic; unless defined otherwise, it preferably contains one or more, in particular 1, 2 or 3, heteroatoms in the heterocyclic ring, preferably selected from the group consisting of N, O and S; it is preferably an aliphatic heterocyclyl radical having 3 to 7 ring atoms or a heteroaromatic radical having 5 or 6 ring atoms. The heterocyclic radical can, for example, be a heteroaromatic radical or ring (heteroaryl), such as, for example, a mono-, bi- or polycyclic aromatic system, in which at least 1 ring contains one or more heteroatoms. It is preferably a heteroaromatic ring having one heteroatom selected from the group consisting of N, O and S, for example pyridyl, pyrrolyl, thienyl or furyl; furthermore, preferably, it is a corresponding heteroaromatic ring having 2 or 3 heteroatoms, for example pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, thiazolyl, thiadiazolyl, oxazolyl, isoxazolyl, pyrazolyl, imidazolyl and triazolyl.
Furthermore preferably, it is a partially or fully hydrogenated heterocyclic radical having one heteroatom selected from the group consisting of N, O and S, for example oxiranyl, oxetanyl, oxolanyl (= tetrahydrofuryl), oxanyl, pyrrolidyl or piperidyl.
Furthermore preferably, it is a partially or fully hydrogenated heterocyclic radical having 2 heteroatoms selected from the group consisting of N, O and S, for example piperazinyl, dioxolanyl, oxazolinyl, isoxazolinyl, oxazolidinyl, isoxazolidinyl and morpholinyl.
Possible substituents for a substituted heterocyclic radical are the substituents mentioned further below, and addit'ronally also oxo. The oxo group can also be present at the hetero ring atoms which can exist in different oxidation states, for example at N
and S.
Substituted radicals, such as a substituted alkyl, alkenyl, alkynyl, aryl, phenyl, benryl, heterocyclyl and heteroaryl radical, are, for example, a substituted radical derived from the unsubstituted skeleton, where the substituents are, for example, one or more, preferably 1, 2 or 3, radicals selected from the group consisting of halogen, alkoxy, haloalkoxy, alkylthio, hydroxyl, amino, nitro, carboxyl, cyano, azido, alkoxycarbonyl, alkylcarbonyl, formyl, carbamoyl, mono- and dialkylaminocarbonyl, substituted amino, such as acylamino, mono- and dialkylamino, and alkylsulfinyl, haloalkylsulfinyl, ,,,." alkylsulfonyl, haloalkylsulfonyl and, in the case of cyclic radicals, also alkyl, haloalkyl alkylthioalkyl, alkoxyalkyl, optionally substituted mono- and dialkylaminoalkyl and hydroxyalkyl; the term "substituted radicals", such as substituted alkyl and the like, includes as substituents, in addition to the saturated hydrocarbon-containing radicals mentioned, the corresponding unsaturated aliphatic and aromatic radicals, such as unsubstituted or substituted alkenyl, alkynyl, alkenyloxy, alkynyloxy, phenyl, phenoxy etc. Substituted cyclic radicals having aliphatic moieties in the ring include cyclic systems having substituents which are attached to the ring via a double bond, for example those substituted by an alkylidene group, such as methylidene or ethylidene.
Among the radicals with carbon atoms, preference is given to those having 1 to carbon atoms, in particular 1 or 2 carbon atoms. In general, preference is given to substituents selected from the group consisting of halogen, for example fluorine and chlorine, (C~-C4)alkyl, preferably methyl or ethyl, (C~-C4)haloalkyl, preferably trifluoromethyl, (C~-C4)alkoxy, preferably methoxy or ethoxy, (C~-C4)haloalkoxy, nitro and cyano. Particular preference is given here to the substituents methyl, methoxy, fluorine and chlorine.
Substituted amino, such as mono- or disubstituted amino, is a radical from the group of the substituted amino radicals which are N-substituted, for example, by one or two identical or different radicals selected from the group consisting of alkyl, alkoxy, acyl and aryl; preferably mono- and dialkylamino, mono- and diarylamino, acylamino, N-alkyl-N-arylamino, N-alkyl-N-acylamino and N-heterocycles; preference is given to alkyl radicals having 1 to 4 carbon atoms; aryl is preferably phenyl or substituted phenyl; for acyl, the definition mentioned further below applies, preferably (C1-C4)alkanoyl. This applies correspondingly to substituted hydroxylamino or hydrazino.
Unsubstituted or substituted phenyl is preferably phenyl which is unsubstituted or mono- or polysubstituted, preferably up to trisubstituted, by identical or different radicals selected from the group consisting of halogen, (C1-C4)alkyl, (C~-C4)alkoxy, (C1-C4)haloalkyl, (C~-C4)haloalkoxy and nitro, for example o-, m- and p-tolyl, dimethylphenyls, 2-, 3- and 4-chlorophenyl, 2-, 3- and 4-trifluoro- and -trichlorophenyl, X10 2,4-, 3,5-, 2,5- and 2,3-dichlorophenyl, o-, m- and p-methoxyphenyl.
Acyl is a radical of an organic acid which is formally formed by removing a hydroxyl group from the acid function, where the organic radical in the acid can also be attached to the acid function via a heteroatom. Examples of aryl are the radical -CO-R
of a carboxylic acid HO-CO-R and radicals of acids derived therefrom, such as thiocarbonic acid, unsubstituted or N-substituted iminocarboxylic acids or the radical of carbonic monoesters, N-substituted carbamic acid, sulfonic acids, sulfinic acids, N-substituted sulfonamide acids, phosphonic acids, phosphinic acids.
Acyl is, for example, formyl, alkylcarbonyl, such as [(C1-C4)alkyl]carbonyl, phenylcarbonyl, alkyloxycarbonyl, phenyloxycarbonyl, benzyloxycarbonyl, ''' alkylsulfonyl, alkylsulfinyl, N-alkyl-1-iminoalkyl and other radicals of organic acids. The radicals can in each case be further substituted in the alkyl or phenyl moiety, for example in the alkyl moiety by one or more radicals selected from the group consisting of halogen, alkoxy, phenyl and phenoxy; examples of substituents in the phenyl moiety are the substituents which have already been mentioned further above generally for substituted phenyl.
Acyl is preferably an acyl radical in the more restricted sense, i.e. a radical of an organic acid where the acid group is directly attached to the carbon atom of an organic radical, for example formyl, alkylcarbonyl, such as acetyl or [(C1-C4)alkyl]carbonyl, phenylcarbonyl, alkylsulfonyl, alkylsulfinyl and other radicals of organic acids.
In particular for reasons of better herbicidal activity, better selectivity and/or easier preparation, the novel compounds of the formula (I) mentioned or their salts of particular interest are those in which individual radicals have one of the preferred meanings already mentioned or mentioned hereinbelow, or, in particular, those, in which one or more of the preferred meanings already mentioned or mentioned 5 hereinbelow are combined.
Of interest are, for example, compounds of the formula (I) according to the invention or salts thereof in which A is a group of the formula NRaRb, in which ~ 10 Ra and R~, independently of one another, are hydrogen, formyl or else aminocarbonyl or else amino(thiocarbonyl) or (C1-Cg)alkyl, (C2-Cg)alkenyl, (C2-Cs)alkynyl, (C~-Cs)alkylsulfinyl, (C~-C6)alkylsulfonyl, (C~-Cg)alkoxy, [(C~-Cg)alkyl]carbonyl, [(C~-Cg)alkoxy]carbonyl or else N-mono[ (C1-Cg)alkyl]aminocarbonyl or else N,N-15 di[(C1-Cg)alkyl]aminocarbonyl or else [(C~-C6)alkylthio]carbonyl or else [(C1-Cg)alkyl](thiocarbonyl) or else [(C1-Cg)alkoxy] (thiocarbonyl) or else N-mono[(C~-Cg)alkyl]amino(thiocarbonyl) or else N,N-di[(C~-C6)alkyl]amino(thiocarbonyl) or else [(C~-Cg)alkylthio](thiocarbonyl), where each of the 16 last-mentioned radicals is unsubstituted or substituted, preferably unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C~-C4)alkoxy, (C~-C4)haloalkoxy, (C~-C4)hydroxyalkoxy and (C~-C4)alkoxy-(C~-C4)alkoxy, or are (C3-C6)cycloalkyl, (C3-Cg)cycloalkoxy, phenyl, phenoxy, phenylamino, phenylcarbonyl or else naphthylcarbonyl or phenylsulfonyl, heterocyclyl, heterocyclyloxy, heterocyclylamino, heterocyclylcarbonyl, heterocyclylsulfonyl, where each of the 13 last-mentioned radicals is unsubstituted or substituted, preferably unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, cyano, (C~-C4)alkyl, (C~-C4)haloalkyl, (C~-C4)alkoxy-(C~-C4)alkyl, (C~-C4)alkoxy, (C~-C4)haloalkoxy and (C~-C4)alkoxy-(C~-C4)alkoxy, and heterocyclyl in the radicals mentioned is in each case heterocyclyl having 3 to 9 ring atoms, 1 to 3 of which are hetero ring atoms selected from the group consisting of N, O and S, or one of the radicals Ra and Rb is as defined above and the other of the radicals Ra and Rb is a group of the formula NR'R", where R' and R", independently of one another, are H or (C1-C4)alkyl, which is unsubstituted or substituted, preferably unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C~-C4)alkoxy, (C~-C4)haloalkoxy and (C~-C4)alkoxy-(C~-C4)alkoxy, or R' and R" together are straight-chain (C2-C5)alkylene, which is unsubstituted or substituted by one or more radicals selected from the group consisting of (C~-C4)alkyl, (C1-C4)alkoxy and (C~-C4)alkoxy-(C~-C4)alkyl, or Ra and Rb together are (C~-Cg)alkylidene, which is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, cyano, (C~-C4)alkoxy, (C~-C4)haloalkoxy and (C1-C4)alkylthio, or NRaRb together are a heterocyclyl radical which is attached to the nitrogen atom and has 3 to 6 ring atoms and, in addition to the nitrogen atom as hetero ring atom, optionally contains 1 to 3 further hetero ring atoms selected from the group consisting of N, O and S, where the heterocycle is unsubstituted or substituted, preferably unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, cyano, (C~-C4)alkyl, (C~-C4)haloalkyl, (C1-C4)alkoxy, (C~-C4)haloalkoxy, (C~-C4)alkoxy-(C~-C4)alkoxy and (C~-C4)alkoxy-(C1-C4)alkyl, or A is (C~-C4)alkyl, (C2-C4)alkenyl, (C2-C4)alkynyl or (C3-C4)cycloalkyl, where each of the 4 last-mentioned radicals is unsubstituted or substituted, preferably unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C~-C4)alkoxy, (C~-C4)haloalkoxy, (C1-C4)alkylthio, (C~-C4)alkoxy-(C1-C4)alkoxy and, in the case of cyclic radicals, also (C~-C4)alkyl, (C1-C4)haloalkyl and (C~-C4)alkoxy-(C1-C4)alkyl, preferably (C~-C3)alkyl, in particular methyl.
Preference is given to compounds of the formula (I) according to the invention or salts thereof in which A is a group of the formula NRaRb, in which Ra is hydrogen or (C~-C4)alkyl and Rb is hydrogen or formyl, or else aminocarbonyl or else amino(thiocarbonyl) or (C~-C4)alkyl, (C~-C4)alkylsulfonyl, [(C~-C4)alkyl]carbonyl or [(C~-C4)alkoxy]carbonyl, where each of the 4 last-mentioned radicals is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen and (Ct-C4)alkoxy, or is (Cg-Cg)cycloalkyl, phenyl, phenoxy, phenylthio, phenylcarbonyl, phenylsulfonyl, where each of the 6 last-mentioned radicals is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C1-C4)alkyl, (C~-C4)haloalkyl, (C~-C4)alkoxy, (C~-C4)haloalkoxy, (C~-C4)alkoxy-(C~-C4)alkyl and (C~-C4)alkoxy-(C~-C4)alkoxy, preferably H, CHO, CO-CH3, CO-C6H5, S02CH3 or S02C2H5, or Ra and Rb together are (C~-C4)alkylidene, which is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, cyano, (C~-C2)alkoxy, (C~-C2)haloalkoxy and (C~-C2)alkylthio, or NRaRb together are a saturated heterocyclyl radical having 5 or 6 ring atoms which, in addition to the nitrogen atom as hetero ring atom, optionally contains 1 to 3 further hetero ring atoms selected from the group consisting of N, O and S, where the heterocycle is unsubstituted or substituted by one or more radicals selected from the group consisting of (C~-C4)alkyl, (C~-C4)haloalkyl, (C~-C4)alkoxy and (C~-C4)haloalkoxy, (C~-C4)alkoxy-(C~-C4)alkyl and (C~-C4)alkoxy-(C~-C4)alkoxy, preferably (C~-C4)alkyl and (C1-C4)alkoxy.
Of interest are, for example, also compounds of the formula (I) according to the invention and salts thereof in which R1 is (C~-Cg)alkyl, which is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, hydroxyl, cyano, nitro, thiocyanato, formyl or else amino, (C1-C4)alkoxy, (C~-C4)haloalkoxy or else N-mono(C~-C4)alkylamino or else N,N-di(C1-C4)alkylamino or (C~-C4)alkylthio, (C~-C4)alkylsulfonyl, (C~-C4)haloalkylsulfonyl, [(C~-C4)alkyl]carbonyl, [(C~-C4)haloalkyl]carbonyl, [(C~-C4)alkoxy]carbonyl, (C3-C9)cycloalkyl, phenyl and heterocyclyl, where each of the 3 last-mentioned radicals is unsubstituted or substituted, preferably unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, cyano, hydroxyl, (C~-C4)alkyl, (C1-C4)haloalkyl, (C~-C4)alkoxy, (C1-C4)haloalkoxy and (C~-C4)alkylthio, and where heterocyclyl in each case preferably contains 3 to 9 ring atoms, 1 to 4 of which are hetero ring atoms selected from the group consisting of N, O and S, or is [(C1-Cg)alkyl)carbonyl, [(C~-Cg)alkoxy]carbonyl or (C~-C4)alkylsulfonyl, where each of the 3 last-mentioned radicals is unsubstituted or substituted, preferably unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C~-C4)alkoxy, (C~-C4)haloalkoxy and (C~-C4)alkylthio, or is (C3-Cg)cycloalkyl, which is unsubstituted or substituted, preferably unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C1-C4)alkyl, (Ct-C4)haloalkyl, (C1-C4)alkoxy, (C~-C4)haloalkoxy and (C~-C4)alkylthio.

Preference is given to compounds of the formula (I) according to the invention or salts thereof in which R~ is (C~-C4)alkyl, such as, for example, methyl, ethyl, n-propyl and isopropyl, or (C~-C4)haloalkyl, such as, for example, 1-fluoroisopropyl, 1-fluoroethyl, 1-fluoropropyl, CF3 and CCI3, or cyclopropyl, cyclobutyl, cyciopentyt, cyclohexyl, 1-methylcyclopropyi, 1-methylcyclobutyl, 1-methylcyclopentyl, 1-methylcyclohexyl or benzyl.
Of interest are, for example, also compounds of the formula (I) according to the invention or salts thereof in which ~~ 10 R2 is H or formyl, (Ct-C4)alkyl, (C2-C4)alkenyl, (C2-C4)alkynyl, (C~-C4)alkylsulfinyl, (Ct-C4)alkylsulfonyl, (C~-C4)alkoxy, [(C~-C4)alkyl]carbonyl, [(Ct-C4)alkoxy]carbonyl, where each of the 8 last-mentioned radicals is unsubstituted or substituted, preferably unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C1-C4)alkoxy and (Ct-C4)haloalkoxy, or (C3-Cg)cycloalkyt, (C3-Cg)cycloalkoxy, phenyl, phenoxy, phenylcarbonyl, phenylsulfonyl, heterocyclyi, heterocyclyloxy, heterocyclylcarbonyl or heterocyclylsulfonyl, where each of the 10 last-mentioned radicals is unsubstituted or substituted and heterocyclyl in the 3 last-mentioned radicals in each case preferably contains 3 to 9 ring atoms, 1 to 4 of which are hetero ring atoms selected from the group consisting of N, O and S, where preferably each of the 10 radicals mentioned is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, cyano, (C~-C4)alkyl, (C~-C4)haloalkyl, (C~-C4)alkoxy and (C~-C4)haloalkoxy, or is a group of the formula NR°Rd, where R~ and Rd, independently of one another, are H, formyl, (C~-C4)alkyl, (C~-C4)alkylsulfonyl, (C~-C4)alkoxy, [(C1-C4)aikyl]carbonyl or [(C~-C4)alkoxyJcarbonyl, where each of the 5 last-mentioned groups is unsubstituted or substituted, preferably unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C~-C4)alkoxy, (C~-C4)haloalkoxy and (C~-C4)alkoxy-(C~-C4)alkoxy, or R° and Rd together are straight-chain (C2-C5)alkylene, which is unsubstituted or substituted by one or more radicals selected from the group consisting of 5 (C~-C4)alkyl, (C~-C4)alkoxy, (C~-C4)alkoxy-(C~-C4)alkyl and oxo.
Preference is given to compounds of the formula (I) according to the invention or salts thereof in which R2 is hydrogen, formyl, (C~-C4)alkyl, (C~-C4)haloalkyl, (C~-C4)alkylsulfonyl, (C~-C4)haloalkylsulfonyl, (C~-C4)alkoxy, (C1-Cq.)haloalkoxy, 10 [(C~-C4)alkyl]carbonyl, [(C~-C4)haloalkyl]carbonyl, [(C1-C4)alkoxy]carbonyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, phenyl, phenylcarbonyl or phenylsulfonyl.
Of interest are, for example, also compounds of the formula (I) according to the 15 invention or salts thereof in which R3 is halogen, CN, N02, SCN or a radical of the formula -X~-A1, where X~ is a direct bond or a divalent group of the formula -O-, -S(O)p-, -S(O)p-O-, -O-S(O)p-, -CO-, -O-CO-, -CO-O-, -S-CO-, -CO-S-, -S-CS-, -CS-S-, -O-CO-O-, -N R~ -, -O-N R~-, -N R~-O-, -N R~-CO-, -CO-N R~-, 20 -O-CO-NR~- or -NR~-CO-O-, preferably -O-, -S(O)p-, -CO-, -O-CO-, -CO-O-, -S-CO-, -CO-S-, -NR~ -, -O-NR~-, -NR~-O-, -NR~-CO-, -CO-NR~-, -O-CO-NR~- or -NR~-CO-O-, in which in each case p is the integer 0, 1 or 2 and R~ is hydrogen, (C~-Cq.)alkyl, (C2-C4)alkenyl, (C2-C4)alkynyl, phenyl, phenyl-(C~-CZ)alkyl, (C3-Cg)cycloalkyl or [(C~-C4)alkyl]carbonyl, and A~ is hydrogen, (C~-Cg)alkyl, (C2-Cg)alkenyl, (C2-Cg)alkynyl, (C3-Cg)cycloalkyl, phenyl or heterocyclyl having 3 to 9 ring atoms and 1 to 3 hetero ring atoms selected from the group consisting of N, O and S, where each of the 6 last-mentioned radicals is unsubstituted or substituted, preferably unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, cyano, (C~-C4)alkyl, (C3-Cg)cycloalkyl, (C~-C4)alkoxy, (C~-C4)haloalkoxy, (C~-C4)alkylthio and, in the case of cyclic radicals, also (C~-C4)haloalkyl and (C~-C4)alkoxy-(C~-C4)alkyl and, including substituents, has preferably up to 16 carbon atoms.
Preference is given to compounds (I) and salts thereof in which R3 is H, (C~-C4)alkyl, preferably methyl or ethyl, or cyclopropyl, cyclobutyl, ,~ 10 cyclopentyl, cyclohexyl or phenyl, where each of the 8 last-mentioned radicals is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen and (C~-C2)alkoxy and, in the case of cyclic radicals, also (C~-C2)alkyl, (C~-C2)haloalkyl and (C~-C4)alkoxy-(C~-C4)alkyl.
Of interest are, for example, also compounds of the formula (I) according to the invention or salts thereof in which each of the radicals R4, R5, R6, R' and R8, independently of one another, is halogen, nitro, cyano, thiocyanato or a radical of the formula -X2-A2, where X2 is a direct bond or a divalent group of the formula -O-, -S(O)q-, -S(O)q-O-, -O-S(O)q-, -S(O)q-NR'-, -NR'-S(O)q-, -CO-, -O-CO-, -CO-O-, -S-CO-, -CO-S-, -S-CS-, -CS-S-, -O-CO-O-, -NR' -, -O-NR'-, -NR'-O-, -NR'-CO-, -CO-NR'-, -O-CO-NR'- or -NR'-CO-O-, preferably -O-, -S(O)q-, -S(O)q-O-, -S(O)q-NR'-, -NR'-S(O)q-, -CO-, -O-CO-, -CO-O-, -S-CO-, -CO-S-, -NR' -, -O-NR'-, -NR'-O-, -NR'-CO-, -CO-NR'-, -O-CO-NR'- or -NR'-CO-O-, in which in each case q is the integer 0, 1 or 2 and Rr, independently of one another, is in each case hydrogen, amino, mono- or di(C~-C4)alkylamino, mono- or di(C~-C4)arylamino, N-(C~-C4)alkyl-N-arylamino, (C~-C4)alkyl, (C2-C4)alkenyl, (C2-C4)alkynyl, phenyl, phenyl(C~-C4)alkyl, phenylcarbonyl, (C3-Cg)cycloalkyl, {C5-C6)cycloalkenyl, [(Ct-C4)alkyl]carbonyl, (C~-C4)alkylsulfonyl, (C1-C4)alkylsulfinyl, phenylsulfonyl or phenylsulfinyl, where each of the 18 last-mentioned radicals is unsubstituted or substituted, preferably unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, cyano, (C1-C4)alkyl, (C~-C4)alkoxy, (C~-C4)haloalkoxy and, in the case of cyclic radicals, also (C1-C4)haloalkyl and (C1-C4)alkoxy-(C~-C4)alkyl, and ,~.,. A2 is hydrogen, (C1-Cg)alkyl, (C2-Cg)alkenyl, (C2-Cg)alkynyl, (Cg-Cg)cycloalkyl, (C5-Cg)cycloalkenyl, phenyl or heterocyclyl having 3 to 6 ring atoms and 1 to 3 hetero ring atoms selected from the group consisting of N, O and S, where each of the 7 last-mentioned radicals are unsubstituted or substituted, preferably unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, cyano, hydroxyl, amino or else mercapto or aminocarbonyl, mono- and di(C1-C4)alkylamino, mono- and diphenylamino, N-(C1-C4)alkyl-N-phenylamino, mono- and di[(C~-C4)alkanoyl]amino, mono- and di-[(C1-C4)alkylsulfonyl]amino, N-{C~-C4)alkyl-N-[(C1-C4)alkanoyl]amino, °"~ (C~-C4)alkyl-N-[(C~-C4)alkylsulfonyl]amino, N-phenyl-N-[(C~-C4)alkanoyl]amino, N-phenyl-N-[(C~-C4)alkylsulfonyl]amino, (C~-C4)alkoxy, (C1-C4)alkylthio, (C~-C4)alkylsulfonyl, (C~-C4)alkylsulfinyl, [(C1-C4)alkyl]carbonyl, [(C~-C4)alkoxy]carbonyl, [(C1-C4)alkyl]carbonyloxy, (Cg-Cg)cycloalkyl, (Cg-Cg)cycloalkoxy, (Cg-Cg)cycloalkylcarbonyl, (Cg-Cg)cycloalkylcarbonyloxy, phenyl, phenoxy, phenylthio, phenylcarbonyl, phenylcarbonyloxy, heterocyclyl, heterocyclyloxy, heterocyclylthio, heterocyclylcarbonyl, heterocyclylcarbonyloxy and, in the case of cyclic radicals, also (C1-Cg)alkyl, where each of the 35 last-mentioned radicals is unsubstituted or substituted, preferably unsubstituted or substituted by one or more of the radicals selected from the group consisting of halogen, cyano, hydroxyl, amino, mono- and di(C~-C4)alkylamino, mono-and di-phenylamino, N-(C~-C4)alkyl-N-phenylamino, (C~-C4)alkoxy, (C~-C4)alkylthio, (C3-Cg)cycloalkyl, (C3-C6)cycloalkoxy, phenyl, phenoxy and phenylthio and, in the case of cyclic radicals, also (C~-C4)alkyl, (C~-C4)haloalkyl and (C~-C4)alkoxy-(Ct-C4)alkyl, and A2, including substituents, has preferably up to 16 carbon atoms, or two adjacent radicals from the group consisting of R4, R5, R6, R' and R8 together with the carbon atoms of the phenyl ring to which they are attached form a fused ring having 4 to 6 ring atoms which is carbocyclic or contains 1 to 3 hetero ring atoms selected from the group consisting of N, O and S and which is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C~-C4)alkyl, (C2-C4)alkenyl, (C2-C4)alkynyl, [(C1-C4)alkyl]carbonyl, (C~-Cs)alkoxy, [(C1-C4)alkoxy]carbonyl, '°'~ (C~-C4)alkylsulfonyl and (C~-C4)alkylsulfinyl, where at least two radicals, preferably 2 or 3 radicals, in particular 2 radicals, from the group consisting of R4, R5, R6, R' and R8 are different from hydrogen.
Preference is also given, for example, to compounds of the formula (I) according to the invention or salts thereof in which each of the radicals R4, R5, R6, R' and R8, independently of one another, is hydrogen, halogen, hydroxyl, amino, vitro, formyl, aminocarbonyl, carboxyl, cyano, thiocyanato or else aminosulfonyl or (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)alkylthio, (C1-C4)alkylsulfonyl, (C1-C4)alkylsulfinyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-Cg)alkylcarbonyl, (C1-Cg)alkoxycarbonyl, (C1-Cg)alkylcarbonyloxy, mono- or di-[(C1-C4)alkyl]amino, mono- and diphenylamino, N-(C1-C4)alkyl-N-phenylamino or else mono- or di[(C1-C4)alkyl]aminosulfonyl, mono- or di[(C1-Cg)alkanoyl]amino, N-[(C1-Cg)alkanoyl]-N-[(C1-C4)alkyl]amino, N-phenyl-N-[(C~-C4)alkanoyl]amino, mono- or di[(C1-Cg)alkylsulfonyl]amino, N-[(C1-Cg)alkylsulfonyl]-N-[(C1-C4)alkyl]amino, N-phenyl-N-[(C~-C4)alkylsulfonyl]amino, where each of the 24 last-mentioned radicals is substituted by one or more radicals selected from the group consisting of halogen, vitro, amino, mono-and di[(C1-C4)alkyl]amino, mono- and diphenylamino, N-(C1-C4)alkyl-N-phenylamino, hydroxyl, cyano, (C1-C4)alkoxy or else mercapto or (C1-C4)alkylthio, (C1-C4)haloalkoxy, (C1-C4)alkylcarbonyl, (C1-C4)alkoxycarbonyl, (C3-Cg)cycloalkyl, (C3-Cg)cycloalkylcarbonyl, (C3-Cg)cycloalkylcarbonyloxy, phenyl, phenoxy, phenylthio, phenylcarbonyl, phenoxycarbonyl, phenylcarbonyloxy, phenylsulfonyl, where the 7 last-mentioned radicals are unsubstituted or optionally substituted in the phenyl radical, or is (C3-Cg)cycloalkyl, (C3-Cg)cycloalkoxy, (C3-Cg)cycloalkylcarbonyl, phenyl, phenoxy, phenylthio, phenylcarbonyl, phenoxycarbonyl, phenylcarbonyloxy or phenylsulfonyl, heterocyclyl, heterocyclyloxy, heterocyclylthio, heterocyclylcarbonyl, heterocyclylcarbonyloxy, where each of the 14 last-mentioned radicals is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, vitro, amino, (C1-C4)alkyl, mono- and di{(C1-C4)alkyl]amino, mono- and di-phenylamino, N-(C1-C4)alkyl-N-phenylamino, hydroxyl, cyano, (C1-C4)alkoxy, (C1-C4)alkylthio, (C1-C4)haloalkoxy, (C1-C4)alkylcarbonyl, (C1-C4)alkoxycarbonyl.
Preference is also given, for example, to compounds of the formula (I) according to the invention or salts thereof in which each of the radicals R4, R5, R6, R' and R8, independently of one another, is (C1-Cg)alkoxy-(C1-Cg)alkyl, (C1-Cg)alkylthio-(C1-C6)alkyl, aminocarbonyl-(C1-C4)alkyl, amino-(C1-C4)alkyl, mono- and di[(C1-C4)alkyl]amino-(C1-C4)alkyl, (C3-Cg)-cycloalkyl-(C1-C4)alkyl, (C3-Cg)-cycloalkyl-(C1-C4)alkenyl, (C3-Cg)cycloalkyl-(C1-C4)alkynyl, (C1-C6)alkylcarbonyl-(C1-Cg)alkyl, (C1-Cg)alkoxycarbonyl-(C1-Cg)alkyl, (C1-Cg)alkylcarbonyloxy-(C 1-Cg)-alkyl, (C1-Cg)cycloalkoxy-(C 1-Cq,)alkyl, (C3-5 Cg)cycloalkylcarbonyl-(C1-C4)alkyl, (C1-Cg)alkoxycarbonyl-(C1-Cg)alkyl, (C1-Cg)alkyicarbonyioxy-(C1-Cg)-alkyl, (C1-Cg)cycloalkoxy-(C1-C4)alkyl, (C3-Cg)cycloalkylcarbonyl-(C1-C4)alkyl, mono- or di(C1-Cg)alkanoylamino-(C1-C4)alkyl, mono- and di[(C1-C4)alkylsulfonyl]amino-(C1-C,~)alkyl, N-(Ct-C4)alkyl-N-[(C1-C4)alkanoyl]amino-(C1-C4)alkyl, (C~-C4)alkyl-N-[(C~-C4)alkylsulfonyl]amino-10 (C1-C4)alkyl, N-phenyl-N-[(C~-C4)aikanoyl]amino-(C1-C4)alkyl, N-phenyl-N-[(Ct-C4)alkylsulfonyl]amino-(C1-C4)alkyl, phenoxy-(C1-Cg)-alkyl, phenylcarbonyl-(C1-Cg)aikyl, phenyloxycarbonyl-(C1-Cg)aikyl, phenylcarbonyloxy(C1-C4)alkyl, phenyl(C1-Cg)alkyl, phenyl(C1-Cg)alkenyl, phenyl-(C1-Cg)alkynyl, heterocyclyl(C1-Cg)alkyl, heterocyclyloxy(C1-Cg)alkyl, heterocyclylthio(C1-Cg}alkyl, heterocyclylsulfonyl(C1-15 Cg)alkyl, heterocyclylamino(C1-Cg)alkyl or one of the 38 last-mentioned radicals which is substituted by one or more radicals selected from the group consisting of halogen, hydroxyl, vitro, cyano, (C1-Cg)alkyl, (C1-Cg}alkoxy, (C1-Cg)alkylthio, (C1-C4)alkylsulfonyl, (C1-Cg)haloalkyl and (C1-Cg)haloalkoxy.
20 Furthermore preferably, each of the radicals R4, R5, R6, R' and R8, independently of one another, is hydrogen, halogen, hydroxyl, amino, vitro, formyl, carboxyl, cyano, (C1-Cg)alkyl, (C1-C4)alkoxy, halo(C1-C4)alkyl, halo(C1-C4)alkoxy, hydroxy(C1-C4)alkyl, hydroxy(G1-C4)alkoxy, (C1-C4)alkoxy-(C1-C4)alkyl, halo(C1-C,~)alkoxy-(C1-C4)alkyl, halo(C1-C4)aikoxy-(C1-Cq,)alkoxy, (C1-C4)alkoxy-(C1-C4)alkoxy, 25 (C3-Cg)cycloalkyl, halo(C3-Cg)cycloalkyl, (C2-C4)alkenyl, halo(C2-C4)alkenyl, (C2-C4)alkynyl, halo(C2-C4)alkynyl, (C1-C4)alkylcarbonyl, (C1-C4)alkoxycarbonyl or else (C1-C4)alkylsulfonyl or else (C1-C~)alkylsulfinyf or else (C1-C4)alkylaminosulfonyl or else di[(C1-C4)alkyl]aminosulfonyl or (C1-C4)alkylcarbonyl-(C1-C4)alkyl, (C1-C4)alkylcarbonyloxy, (C1-C4)alkylthio(C1-C4)alkyl, mercapto(C1-C4)alkyl, amino(C1-C4)alkyl, (C1-Cq,)alkylamino, (C1-C4)alkylamino-(C1-C4)alkyl, di[(C1-Cq,)-alkyl]amino, di((C1-C4)-alkyl]amino-(C1-C4)alkyl, (C1-C4)alkanoylamino, (C1-C4)alkylsulfonylamino, di[(C1-C4)alkanoyl]amino, di[(C1-C4)alkylsulfonyl]amino or phenyl, phenoxy, phenylcarbonyl, phenoxycarbonyl, phenylcarbonyloxy, phenoxy(C1-C4)alkyl, phenylcarbonyl(C1-C4)alkyl, phenyl(C1-C4)alkyl or one of the 8 last-mentioned radicals which is substituted in the phenyl moiety by one or more radicals selected from the group consisting of halogen, (C1-C4)alkyl, (C1-C4)alkoxy, (C1-C4)haloalkyl and (C1-C4)haloalkoxy and also hydroxyl.

Furthermore preferably, each of the radicals R4, R5, R6, R' and R8, independently of one another, is hydrogen, hydroxyl, amino, nitro, formyl, carboxyl, cyano, fluorine, chlorine, bromine, iodine, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, t-butyl, sec-butyl, methoxy, ethoxy, n-propoxy, isopropoxy, CF3, CHF2, CH2F, CCIg, OCHF2, OCFg, OCH2F, CH2NH2, CH2CH2NH2, CH20H, CH2CH20H, CH2SH, CH2CH2SH, OCH2CH20H, OCH(CH3)OH, CH20CH3, CH20C2H5, CH2CH20CH3, CH2CH20C2H5, OCH20CH3, OCH20C2H5, OCH2CH20CHg, OCH2CH20C2H5, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, 1-fluorocyclopropyl, vinyl, allyl, prop-1-enyl, 1-methyl-prop-1-enyl, 1-ethyl-prop-1-enyl, but-1-enyl, but-2-en-1-yl, but-3-en-1-yl, z0 ethynyl, propargyl, prop-1-yn-1-yl, but-1-yn-1-yl, but-2-yn-1-yl, but-3-yn-1-yl, 1-methyl-prop-1-yn-1-yl, acetyl, propionyl, propylcarbonyl, methylsulfonyl, ethylsulfonyl, methylsulfinyl, ethylsulfinyl, aminosulfonyl, methylaminosulfonyl, ethylaminosulfonyl;
propylaminosulfonyl, isopropylaminosulfonyl, dimethylaminosulfonyl, diethylaminosulfonyl, methoxycarbonyl, ethoxycarbonyl, methoxycarbonyloxy, ethoxycarbonyloxy, methoxycarbonylmethyl, ethoxycarbonylmethyl, methoxycarbonyloxymethyl, ethoxycarbonyloxymethyl, methylthio, ethylthio, propylthio, methylthiomethyl, ethylthiomethyl, methylthioethyl, ethylthioethyl, methylamino, ethylamino, propylamino, isopropylamino, dimethylamino, diethylamino, methylaminomethyl, ethylaminomethyl, dimethylaminomethyl, diethylaminoethyl, formylamino, acetylamino, formylaminomethyl, formylaminoethyl, methylsulfonylamino, ethylsulfonylamino, dimethylsulfonylamino, diethylsulfonylamino, methylsulfonylaminomethyl, ethylsulfonylaminomethyl, dimethylsulfonylaminomethyl, diethylsulfonylaminomethyl, phenyl, phenoxy, phenylcarbonyl, phenoxycarbonyl, phenylcarbonyloxy, phenoxymethyl, phenoxyethyl, phenylcarbonylmethyl, phenylcarbonylethyl, phenylmethyl (benzyl), phenylethyl (phenethyl) or one of the 11 last-mentioned radicals which is substituted in the phenyl moiety by one or more radicals selected from the group consisting of halogen, (C1-C4)alkyl, (C1-C4)alkoxy, (C1-C4)haloalkyl, (C1-C4)haloalkoxy and hydroxyl.
Of particular interest are compounds of the formula (I) and salts thereof in which R~ is methyl which is unsubstituted or substituted as mentioned above.
Of particular interest are also compounds of the formula (I) according to the invention and salts thereof in which R~ is (C~-C~p)alkyl which is unsubstituted or substituted by substituents according to the invention other than halogen.
Of particular interest are also compounds of the formula (I) according to the invention and salts thereof in which R~ is different from unsubstituted or substituted (Ct-C~ p)alkyl.
Of particular interest are also compounds of the formula (I) according to the invention and salts thereof in which R5, R6, R~ and R8 are each different from (C1-C~p)alkyl or (C~ -C~ p)alkoxy.
Of particular interest are also compounds of the formula (I) according to the invention and salts thereof in which R3 is different from methyl, i.e., for example, (C2-C1p)alkyl, which is unsubstituted, or (C~-C~p)alkyl, which is substituted, or one of the other definitions according to the invention of R3.
The present invention also provides processes for preparing the compounds of the formula (I) or salts thereof, which comprise a) reacting a compound of the formula (II), R~ - Fu (II) in which Fu is a functional group selected from the group consisting of the carboxylic esters, carboxylic orthoesters, carbonyl chlorides, carboxamides, carboxylic anhydrides and trichloromethyl with a biguanide of the formula (III) or an acid addition salt thereof A~N~N ~ R5 (111) H
R2 8 ~ / 6 R Y 'R

or b) reacting a compound of the formula (IV), N_ \ N
,~~, (IV) ~N~Z~
A
in which Z~ is an exchangeable radical or a leaving group, for example chlorine, trichloromethyl, (C~-C4)alkylsulfonyl and unsubstituted or substituted phenyl-24 (C~-C4)alkylsulfonyl or (C~-C4)alkylphenylsulfonyl, with a suitable amine of the formula (V) or an acid addition salt thereof RJ (V) R Q ~ ~ Q6 R~
where in the formulae (II), (III), (IV) and (V) the radicals Rt, R2, R3, R4, R5, R6, R', R8 and A are as defined in formula (I).
The compounds of the formula (II) and (III) are preferably reacted base-catalyzed in an inert organic solvent, such as, for example, tetrahydrofuran (THF), dioxane, acetonitrile, dimethylformamide (DMF), methanol and ethanol, at temperatures between -10°C and the boiling point of the solvent, preferably at from 20°C to 60°C; if acid addition salts of the formula (III) are used, these are generally liberated in situ with the aid of a base. Suitable bases or basic catalysts are alkali metal hydroxides, alkali metal hydrides, alkali metal carbonates, alkali metal alkoxides, alkaline earth metal hydroxides, alkaline earth metal hydrides, alkaline earth metal carbonates or organic bases, such as triethylamine or 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU).
The base in question is employed, for example, in the range from 0.1 to 3 molar equivalents, based on the compound of the formula (III). Based on the compound of the formula (III), the compound of the formula (II) can be employed, for example, in '~ equimolar amounts or in an excess of up to 2 molar equivalents. In principle, the corresponding processes are known from the literature (compare: Comprehensive Heterocyclic Chemistry, A.R. Katritzky, C.W. Rees, Pergamon Press, Oxford, New York, 1984, Vol.3; Part 2B; ISBN 0-08-030703-5, p.290).
The compounds of the formulae (IV) and (V) are preferably reacted base-catalyzed in an inert organic solvent, such as, for example, THF, dioxane, acetonitrile, DMF, methanol and ethanol, at temperatures between -10°C and the boiling point of the solvent or solvent mixture in question, preferably at from 20°C to 60°C, in particular at from 30°C to 80°C, where the compound (V), if it is employed as acid addition salt, is, if appropriate, liberated in situ using a base. Suitable bases or basic catalysts are alkali metal hydroxides, alkali metal hydrides, alkali metal carbonates, alkali metal alkoxides, alkaline earth metal hydroxides, alkaline earth metal hydrides, alkaline earth metal carbonates or organic bases such as triethylamine or 1,8-diaza-bicyclo[5.4.0]undec-7-ene (DBU). The base in question is generally employed in the range from 1 to 3 molar equivalents, based on the compound of the formula (IV), and 5 the compound of the formula (IV) can be employed, for example, in equimolar amounts or in an excess of up to 2 molar equivalents, based on the compound of the formula (V). In principle, the corresponding processes are known from the literature (cf.
Comprehensive Heterocyclic Chemistry, A.R. Katritzky, C.W. Rees, Pergamon Press, Oxford, New York, 1984, Vol.3; Part 2B; ISBN 0-08-030703-5, p. 482).
,,~,.. The starting materials of the formulae (II), (III), (IV) and (V) are either commercially available, or they can be prepared by or analogously to processes known from the literature. Some of the compounds of the formulae (III) are novel, and they also form part of the subject matter of the invention. The compounds can also be prepared, for example, by one of the processes described below.
The compound of the formula (IV), or a direct precursor thereof, can be prepared, for example, as follows:
1. Reaction of a compound of the formula (II) with an amidinothiourea derivative of the formula (VI), NH
~ Z 2 (VI) N~S~
H
in which Z2 is (C~-C4)alkyl or phenyl(C~-C4)alkyl and A is as defined in formula (I) gives compounds of the formula (IV) in which Z1 - -SZ2.
2. Reaction of amidine of the formula (VII) or an acid addition salt thereof H2N-CRS=NH (VII) ' 31 in which R1 is as defined in formula (I) with a N-cyanodithioiminocarbonate of the formula (VIII), NC-N=C(S-Z3)2 (VIII) in which Z3 is (C~-C4)alkyl or phenyl(C~-C4)alkyl gives compounds of the formula (IV) in which Z~ - -S-Z3.
3. Reaction of an alkali metal dicyanamide with a carboxylic acid derivative of the "~10 formula (II) mentioned gives compounds of the formula (IV) in which Z~ =
NH2, 4. Reaction of trichloroacetonitrile with a nitrite of the formula (IX), R1 - CN (IX) in which R~ is as defined in formula (I) initially gives compounds of the formula (X), R~
N_ \ N X
( ) Z~N~Z~
in which Z~ and Z4 are each CCI3 which, by subsequent reaction with compounds of the formula H-A (A is as defined in formula (I)), gives compounds of the formula (IV) in which Z1 = CCIg.
The substituted phenyl alkyl amines of the formula (V) required as starting materials are known and/or can be prepared by processes known per se. For example, the corresponding aromatic ketone can be reductively aminated directly to the amine, for example by reaction with sodium cyanoborohydride and ammonium acetate or with a mixture of ammonium formate and formic acid followed by cleavage of the amide, or the ketone is converted into an advantageous derivative, for example an oxime, which is then reduced to the amine (cf. JP 11035536; JP 11043470; J. Am. Chem. Soc.
1983, 105, 1578; Synthesis 1980, 695).
The reaction of the carboxylic acid derivatives of the formula (II) with the amidinothiourea derivatives of the formula (VI) is preferably carried out base-catalyzed in an organic solvent, such as, for example, acetone, THF, dioxane, acetonitrile, DMF, methanol, ethanol, at temperatures from -10°C to the boiling point of the solvent, preferably at from 0°C to 20°C. However, the reaction can also be carried out in water ,,.,. or in aqueous solvent mixtures with one or more of the abovementioned organic solvents. If (VI) is employed as acid addition salt, it can, if appropriate, be liberated in situ using a base. Suitable bases or basic catalysts are alkali metal hydroxides, alkali metal hydrides, alkali metal carbonates, alkali metal alkoxides, alkaline earth metal hydroxides, alkaline earth metal hydrides, alkaline earth metal carbonates or organic bases, such as triethylamine or 1,8-diazabicyclo[5.4.OJundec-7-ene (DBU). The base in question is, for example, employed in the range from 1 to 3 molar equivalents, based on the compound of the formula (VI). Compounds of the formula (II) and (VI) can be employed, for example, in equimolar amounts, or with an excess of up to molar equivalents of the compound of the formula (II). In principle, the corresponding processes are known from the literature (compare: H. Eilingsfeld, H.
Scheuermann, Chem. Ber.; 1967, 100, 1874); the corresponding intermediates of the formula (IV) are novel.
The reaction of the amidines of the formula (VII) with the N-cyanodithioiminocarbonates of the formula (VIII) is preferably carried out base-catalyzed in an inert organic solvent, such as, for example, acetonitrile, DMF, dimethylacetamide (DMA), N-methylpyrrolidone (NMP), methanol and ethanol, at temperatures from -10°C to the boiling point of the solvent, preferably at from 20°C to 80°C. If (VII) is employed as acid addition salt, it can, if appropriate, be liberated in situ using a base. Suitable bases or basic catalysts are alkali metal hydroxides, alkali metal hydrides, alkali metal carbonates, alkali metal alkoxides, alkaline earth metal hydroxides, alkaline earth metal hydrides, alkaline earth metal carbonates or organic bases, such as triethylamine or 1,8-diazabicyclo[5.4.OJundec-7-ene (DBU). The base in question is employed, for example, in the range from 1 to 3 molar equivalents, based on the compound of the formula (VIII), and compounds of the formulae (VII) and (VIII) can generally be employed in equimolar amounts or with an excess of two molar equivalents of the compound of the formula (II). In principle, the corresponding processes are known from the literature (compare: T.A. Riley, W.J. Henney, N.K.
Dalley, B.E. Wilson, R.K. Robins; J. Heterocyclic Chem.; 1986, 23 (6), 1706-1714); the corresponding intermediates of the formula (IV) are novel.
Intermediates of the formula (X) where Z1 = chlorine can be prepared by reacting alkali metal dicyanamide with a carboxylic acid derivative of the formula (II), Fu then '"'"~"" preferably being the functional group carbonyl chloride or carboxamide. The reaction of the reaction components is carried out, for example, acid-catalyzed in an inert organic solvent, such as, for example, toluene, chlorobenzene, chlorinated hydrocarbons, at temperatures between -10°C and the boiling point of the solvent, preferably at from 20°C to 80°C, where the intermediates formed can be chlorinated in situ using a suitable chlorinating agent, such as, for example, phosphorus oxychloride.
Suitable acids are, for example, hydrohalic acids, such as HCI, or else Lewis acids, such as, for example, AICI3 or BF3 (compare US-A-5095113, DuPont).
Intermediates of the formula (X) where Z1, Z4 = trihalomethyl can be prepared by reacting the corresponding trihaloacetonitriles with a carbonitrile of the formula (IX).
The reaction of the reaction components is carried out, for example, acid-catalyzed in an inert organic solvent, such as, for example, toluene, chlorobenzene, chlorinated hydrocarbons, at temperatures between -40°C and the boiling point of the solvent, preferably at from -10°C to 30°C. Suitable acids are, for example, hydrohalic acids, such as HCI, or else Lewis acids, such as, for example, AICIg or BF3 (cf.
EP-A-130939, Ciba Geigy).
Intermediates of the formula (IV), in which Z~ _ (C~-C4)alkylmercapto or unsubstituted phenyl(C~-C4)alkylmercapto, can be converted in an inert organic solvent, such as, for example toluene, chlorobenzene, chlorinated hydrocarbons or others, at temperatures between -40°C and the boiling point of the solvent, preferably at from 20°C to 80°C, with a suitable chlorinating agent, such as, for example elemental chlorine or phosphorus oxychloride, into more reactive chlorotriazines of the formula (IV), in which Z~ = CI (cf. J.K. Chakrabarti, D.E. Tupper; Tetrahedron 1975, 31(16), 1879-1882).
Intermediates of the formula (IV), in which Z~ _ (C~-C4)alkylmercapto or unsubstituted or substituted phenyl(C~-Cq,)alkylmercapto or (C1-C4)alkylphenylthio, can be oxidized in a suitable solvent, such as, for example, chlorinated hydrocarbons, acetic acid, water, alcohols, acetone or mixtures thereof at temperatures between 0°C and the boiling point of the solvent, preferably at from 20°C to 80°C, with a suitable oxidizing agent, such as, for example, m-chloroperbenzoic acid, hydrogen peroxide, potassium x.10 peroxomonosulfate (compare: T.A. Riley, W.J. Henney, N.K. Dalley, B.E.
Wilson, R.K.
Robins; J. Heterocyclic Chem.; 1986, 23 (6), 1706-1714).
The following acids are suitable for preparing the acid addition salts of the compounds of the formula (I): hydrohalic acids, such as hydrochloric acid or hydrobromic acid, furthermore phosphoric acid, nitric acid, sulfuric acid, mono- or bifunctional carboxylic acids and hydroxycarboxylic acids, such as acetic acid, malefic acid, succinic acid, fumaric acid, tartaric acid, citric acid, salicylic acid, sorbic acid or lactic acid, and also sulfonic acids, such as p-toluenesulfonic acid and 1,5-naphthalenedisulfonic acid. The acid addition compounds of the formula (I) can be obtained in a simple manner by the customary methods for forming salts, for example by dissolving a compound of the formula (I) in a suitable organic solvent, such as, for example, methanol, acetone, methylene chloride or benzene, and adding the acid at temperatures from 0 to 100°C, and they can be isolated in a known manner, for example by filtration, and, if appropriate, purified by washing with an inert organic solvent.
The base addition salts of the compounds of the formula (I) are preferably prepared in inert polar solvents, such as, for example, water, methanol or acetone, at temperatures from 0 to 100°C. Examples of bases which are suitable for the preparation of the salts according to the invention are alkali metal carbonates, such as potassium carbonate, alkali metal hydroxides and alkaline earth metal hydroxides, for example NaOH
or KOH, alkali metal hydrides and alkaline earth metal hydrides, for example NaH, alkali metal alkoxides and alkaline earth metal alkoxides, for example sodium methoxide or potassium tert-butoxide, or ammonia or ethanolamine.

Solvents referred to as "inert solvents" in the above process variants are to be understood as meaning in each case solvents which are inert under the reaction conditions in question, but which need not be inert under all reaction conditions.

A collection of compounds (I) which can be synthesized by the abovementioned process may also be prepared in a parallel manner where the process may be carried out manually, partially automated or fully automated. In this case, it is possible to automate the procedure of the reaction, the work-up or the purification of the products 10 or of the intermediates. In total, this is to be understood as meaning a procedure as is described, for example, by S. H. DeWitt in "Annual Reports in Combinatorial Chemistry and Molecular Diversity: Automated Synthesis", Volume 1, Verlag Escom, 1997, pages 69 to 77.
15 A number of commercially available apparatuses as are offered by, for example, Stem Corporation, Woodrolfe Road, Tollesbury, Essex, CM9 8SE, England and H+P
t_abortechnik GmbH, Bruckmannring 28, 85764 Oberschlei(3heim, Germany may be used for the parallel procedure of the reaction and work-up. For the parallel purification of compounds (I), or of intermediates obtained during the preparation, use may be 20 made, inter alia, of chromatography apparatuses, for example those from ISCO, Inc., 4700 Superior Street, Lincoln, NE 68504, USA. The apparatuses mentioned lead to a modular procedure in which the individual process steps are automated, but manual operations have to be performed between the process steps. This can be avoided by employing semi-integrated or fully integrated automation systems where the 25 automation modules in question are operated by, for example, robots. Such automation systems can be obtained, for example, from Zymark Corporation, Zymark Center, Hopkinton, MA 01748, USA.
In addition to the methods described here, compounds (I) may be prepared in part or 30 fully by solid-phase-supported methods. For this purpose, individual intermediate steps or all intermediate steps of the synthesis or of a synthesis adapted to suit the procedure in question are bound to a synthetic resin. Solid-phase-supported synthesis methods are described extensively in the specialist literature, for example Barry A.
Bunin in "The Combinatorial Index", Verlag Academic Press, 1998.

3s The use of solid-phase-supported synthesis methods permits a series of protocols which are known from the literature and which, in turn, can be performed manually or in an automated manner. For example, the "tea-bag method" (Houghten, US
4,631,211; Houghten et al., Proc. Natl. Acad. Sci, 1985, 82, 5131-5135), in which products from IRORI, 11149 North Torrey Pines Road, La Jolla, CA 92037, USA, are employed, may be partially automated. The automation of solid-phase-supported parallel synthesis is performed successfully, for example, by apparatuses from Argonaut Technologies, Inc., 887 Industrial Road, San Carlos, CA 94070, USA or MultiSynTech GmbH, Wullener Feld 4, 58454 Witten, Germany.
The preparation methods described here give compounds (I) in the form of collections of substances known as libraries. The present invention also relates to libraries of the compounds (I) which contain at least two compounds (I) and their intermediates.
The compounds of the formula (I) according to the invention and their salts, hereinbelow together referred to as compounds of the formula (I) (according to the invention), have excellent herbicidal activity against a broad spectrum of economically important monocotyledonous and dicotyledonous harmful plants. The active compounds also act efficiently on perennial weeds which produce shoots from rhizomes, root stocks or other perennial organs and which are difficult to control. In this context, it is generally immaterial whether the substances are applied pre-sowing, pre-emergence or post-emergence.
Specifically, examples may be mentioned of some representatives of the monocotyledonous and dicotyledonous weed flora which can be controlled by the compounds according to the invention, without these being a restriction to certain species.
Examples of weed species on which the active compounds act efficiently are, from amongst the monocotyledons, Avena, Lolium, Alopecurus, Phalaris, Echinochloa, Digitaria, Setaria and also Cyperus species from the annual sector and, from amongst the perennial species, Agropyron, Cynodon, tmperata and Sorghum, and also perennial Cyperus species.
In the case of the dicotyledonous weed species, the spectrum of act'ron extends to species such as, for example, Galium, Viola, Veronica, Lamium, Stellaria, Amaranthus, Sinapis, Ipomoea, Matricaria, Abutilon and Sida from amongst the annuals, and Convolvulus, Cirsium, Rumex and Artemisia in the case of the perennial weeds.
The active compounds according to the invention also effect outstanding control of harmful plants which occur under the specific conditions of rice-growing such as, for example, Sagittaria, Alisma, Eleocharis, Scirpus and ~Cyperus.
If the compounds according to the invention are applied to the soil surface prior to germination, then the weed seedlings are either prevented completely from emerging, or the weeds grow until they have reached the cotyledon stage but then their growth stops, and, eventually, after three to four weeks have elapsed, they die completely.
If the active compounds are applied post-emergence to the green parts of the plants, growth also stops drastically a very short time after the treatment and the weed plants remain at the developmental stage of the point in time of application, or they die completely after a certain time, so that in this manner competition from the weeds, which is harmful to the crop plants, is eliminated at a very early point in time and in a sustained manner.
Although the compounds according to the invention have an excellent herbicidal activity against monocotyledonous and dicotyledonous weeds, crop plants of economically important crops, for example wheat, barley, rye, rice, corn, sugar beet, cotton and soya, are not damaged at all, or only to a negligible extent. For these reasons, the present compounds are highly suitable for selectively controlling undesired plant growth in plantings of agriculturally useful plants.
In addition, the substances according to the invention have outstanding growth-regulating properties in crop plants. They engage in the plant metabolism in a regulating manner and can thus be employed for the targeted control of plant constituents and for facilitating harvesting, such as for example by provoking desiccation and stunted growth. Furthermore, they are also suitable for generally regulating and inhibiting undesirable vegetative growth, without destroying the plants in the process. Inhibition of vegetative growth plays an important role in many monocotyledonous and dicotyledonous crops because lodging can be reduced hereby, or prevented completely.

Owing to their herbicidal and plant-growth-regulatory properties, the active compounds can also be employed for controlling harmful plants in crops of known or still to be developed genetically engineered plants. The transgenic plants generally have particularly advantageous properties, for example resistance to certain pesticides, in particular certain herbicides, resistance to plant diseases or causative organisms of plant diseases, such as certain insects or microorganisms such as fungi, bacteria or viruses. Other particular properties relate, for example, to the quantity, quality, storage stability, composition and to specific ingredients of the harvested product.
Thus, transgenic plants having an increased starch content or a modified quality of the starch or those having a different fatty acid composition of the harvested product are known.
The use of the compounds of the formula (I) according to the invention or their salts in economically important transgenic crops of useful and ornamental plants, for example of cereals, such as wheat, barley, rye, oats, millet, rice, manioc and corn, or else in crops of sugar beet, cotton, soya, oilseed rape, potato, tomato, pea and other vegetable species is preferred.
The compounds of the formula (i) can preferably be used as herbicides in crops of useful plants which are resistant or which have been made resistant by genetic engineering toward the phytotoxic effects of the herbicides.
Conventional ways of preparing novel plants which have modified properties compared to known plants comprise, for example, traditional breeding methods and the generation of mutants. Alternatively, novel plants having modified properties can be produced with the aid of genetic engineering methods (see, for example, EP-A-0221044, EP-A-0131624). For example, there have been described several cases of genetically engineered changes in crop plants in order to modify the starch synthesized in the plants (for example WO 92111376, WO 92114827 and WO 91/19806), transgenic crop plants which are resistant to certain herbicides of the glufosinate-type (cf., for example, EP-A-0242236, EP-A-0242246) or glyphosate-type (WO 92100377), or of the sulfonylurea-type (EP-A-0257993, US-A-5013659), transgenic crop plants, for example cotton, having the ability to produce Bacillus thuringiensis toxins (Bt toxins) which impart resistance to certain pests to the plants (EP-A-0142924, EP-A-0193259), transgenic crop plants having a modified fatty acid composition (WO 91/13972).
Numerous molecular biological techniques which allow the preparation of novel transgenic plants having modified properties are known in principle; see, for example, Sambrook et al., 1989, Molecular Cloning, A Laboratory Manual, 2nd ed. Cold Spring Harbor Laboratory Press, Cold Spring Harbor, NY; or Winnacker "Gene and Klone"
[Genes and Clones], VCH Weinheim, 2nd edition 1996, or Christou, "Trends in Plant ,~.,. Science" 1 (1996) 423-431 ).
In order to carry out such genetic engineering manipulations, it is possible to introduce nucleic acid molecules into plasmids which allow a mutagenesis or a change in the sequence to occur by recombination of DNA sequences. Using the abovementioned standard processes it is possible, for example, to exchange bases, to remove partial sequences or to add natural or synthetic sequences. To link the DNA fragments with each other, it is possible to attach adaptors or linkers to the fragments.
Plant cells having a reduced activity of a gene product can be prepared, for example, by expressing at least one appropriate antisense-RNA, a sense-RNA to achieve a cosuppression effect, or by expressing at least one appropriately constructed ribozyme which specifically cleaves transcripts of the abovementioned gene product.
To this end, it is possible to employ both DNA molecules which comprise the entire coding sequence of a gene product including any flanking sequences that may be present, and DNA molecules which comprise only parts of the coding sequence, it being necessary for these parts to be long enough to cause an antisense effect in the cells. It is also possible to use DNA sequences which have a high degree of homology to the coding sequences of a gene product but which are not entirely identical.
When expressing nucleic acid molecules in plants, the synthesized protein can be localized in any desired compartment of the plant cell. However, to achieve localization in a certain compartment, it is, for example, possible to link the coding region with DNA

sequences which ensure localization in a certain compartment. Such sequences are known to the person skilled in the art (see, for example, Braun et al., EMBO
J. 11 (1992), 3219-3227; Wolter et al., Proc. Natl. Acad. Sci. USA 85 (1988), 846-850;
Sonnewald et al., Plant J. 1 (1991 ), 95-106).

The transgenic plant cells can be regenerated to whole plants using known techniques. The transgenic plants can in principle be plants of any desired plant species, i.e. both monocotyledonous and dicotyledonous plants.
10 In this manner, it is possible to obtain transgenic plants which have modified properties ,~", by overexpression, suppression or inhibition of homologous (= natural) genes or gene sequences or by expression of heterologous (= foreign) genes or gene sequences.
The compounds (I) according to the invention can preferably be used in transgenic 15 crops which are resistant to herbicides selected from the group consisting of the sulfonylureas, imidazolinones, glufosinate-ammonium or glyphosate-isopropylammonium and analogous active compounds.
When using the active compounds according to the invention in transgenic crops, in 20 addition to the effects against harmful plants which can be observed in other crops, there are frequently effects which are specific for the application in the respective transgenic crop, for example a modified or specifically broadened spectrum of weeds which can be controlled, modified application rates which can be used for the application, preferably good combinability with the herbicides to which the transgenic 25 crop is resistant, and an effect on the growth and the yield of the transgenic crop plants.
The invention therefore also provides for the use of the compounds (1) according to the invention as herbicides for controlling harmful plants in transgenic crop plants.
The compounds according to the invention can be applied in the customary formulations in the form of wettable powders, emulsifiable concentrates, sprayable solutions, dusts or granules. The invention therefore also provides herbicidal and plant-growth-regulating compositions comprising compounds of the formula (I).

The compounds of the formula (I) can be formulated in various ways depending on the prevailing biological andlor chemico-physical parameters. Examples of suitable formulation options are: wettable powders {WP), water-soluble powders (SP), water-soluble concentrates, emulsifiable concentrates (EC), emulsions (EW), such as oil-in-water and water-in-oil emulsions, sprayable solutions, suspension concentrates (SC), oil- or water-based dispersions, oil-miscible solutions, capsule suspensions (CS), dusts (DP), seed-dressing compositions, granules for broadcasting and soil application, granules (GR) in the form of microgranules, spray granules, coating granules and adsorption granules, water-dispersible granules (WG), water-soluble ",~,, granules (SG), ULV formulations, microcapsules and waxes.
These individual formulation types are known in principle and are described, for example, in Winnacker-Kuchler, "Chemische Technologic" [Chemical Technology], Volume 7, C. Hauser Verlag Munich, 4th edition 1986; Wade van Valkenburg, "Pesticide Formulations", Marcel Dekker, N.Y., 1973; K. Martens, "Spray Drying"
Handbook, 3rd ed. 1979, G. Goodwin Ltd. London.
The necessary formulation auxiliaries, such as inert materials, surfactants, solvents and other additives, are likewise known and are described, for example, in:
Watkins, "Handbook of Insecticide Dust Diluents and Carriers", 2nd ed., Darland Books, Caldwell N.J., H.v. Olphen, "Introduction to Clay Colloid Chemistry"; 2nd ed., J. Wiiey & Sons, N.Y.; C. Marsden, "Solvents Guide"; 2nd ed., Interscience, N.Y. 1963;
McCutcheon's "Detergents and Emulsifiers Annual", MC Publ. Corp., Ridgewood N.J.;
Sisley and Wood, "Encyclopedia of Surface Active Agents", Chem. Publ. Co.
Inc., N.Y.
1964; Schonfeldt, "Grenzflachenaktive Athylenoxidaddukte" [Surface-active ethylene oxide adducts], Wiss. Verlagsgesell., Stuttgart 1976; Winnacker-Kiachler, "Chemische Technologic" [Chemical Technology], Volume 7, C. Hauser Verlag Munich, 4th edition 1986.
Based on these formulations it is also possible to produce combinations with other pesticidally active substances, for example insecticides, acaricides, herbicides and fungicides, and also with safeners, fertilizers andlor growth regulators, for example in the form of a ready-mix or tank mix.

Wettable powders are preparations which are uniformly dispersible in water and which, in addition to the active compound and as well as a diluent or inert substance, also contain surfactants of ionic and/or nonionic type (wetting agents, dispersants), for example polyethoxylated alkyl phenols, polyethoxylated fatty alcohols, polyethoxylated fatty amines, fatty alcohol polyglycol ethersulfates, alkanesulfonates, alkylbenzenesulfonates, sodium ligninsulfonate, sodium 2,2'-dinaphthylmethane-6,6'-disulfonate, sodium dibutylnaphthalenesulfonate or else sodium oleoylmethyltaurinate.
To prepare the wettable powders, the herbicidally active compounds are finely ground, for example in customary apparatuses such as hammer mills, fan mills and air-jet mills, '""' and are mixed simultaneously or subsequently with the formulation auxiliaries.
Emulsifiable concentrates are prepared by dissolving the active compound in an organic solvent, for example butanol, cyclohexanone, dimethylformamide, xylene or else relatively high-boiling aromatics or hydrocarbons or mixtures of the organic solvents, with the addition of one or more surfactants of ionic andlor nonionic type (emulsifiers). Examples of emulsifiers which can be used are calcium alkylarylsulfonates, such as Ca dodecylbenzenesulfonate, or nonionic emulsifiers, such as fatty acid polyglycol esters, alkylaryl polyglycol ethers, fatty alcohol polyglycol ethers, propylene oxide-ethylene oxide condensation products, alkyl polyethers, sorbitan esters, for example sorbitan fatty acid esters or polyoxyethylene sorbitan ..~. esters, for example polyoxyethylene sorbitan fatty acid esters.
Dusts are obtained by grinding the active compound with finely divided solid substances, for example talc, natural clays, such as kaolin, bentonite and pyrophyllite, or diatomaceous earth.
Suspension concentrates can be water- or oil-based. They can be prepared, for example, by wet milling using commercially customary bead mills, with or without the addition of surfactants as already mentioned above, for example, in the case of the other formulation types.
Emulsions, for example oil-in-water emulsions (EW), can be prepared for example by means of stirrers, colloid mills and/or static mixers using aqueous organic solvents and, if desired, surtactants as already mentioned above, for example, in the case of the other formulation types.
Granules can be prepared either by spraying the active compound onto adsorptive, granulated inert material or by applying active-compound concentrates to the surface of carriers such as sand, kaolinites or granulated inert material, by means of adhesive binders, for example polyvinyl alcohol, sodium polyacrylate or else mineral oils.
Suitable active compounds can also be granulated in the manner which is customary for the preparation of fertilizer granules, if desired as a mixture with fertilizers.
f"" Water-dispersible granules are generally prepared by the customary processes, such as spray-drying, fluidized-bed granulation, disk granulation, mixing using high-speed mixers, and extrusion without solid inert material. For the preparation of disk, fluidized-bed, extruder and spray granules, see for example processes in "Spray-Drying Handbook" 3rd ed. 1979, G. Goodwin Ltd., London; J.E. Browning, "Agglomeration", Chemical and Engineering 1967, pages 147 ff; "ferry's Chemical Engineer's Hand-book", 5th ed., McGraw-Hill, New York 1973, pp. 8-57.
For further details on the formulation of crop protection products, see for example G.C. Klingman, "Weed Control as a Science", John Wiley and Sons., Inc., New York, 1961, pages 81-96 and J.D. Freyer, S.A. Evans, "Weed Control Handbook", 5th ed., ,,.., Blackwell Scientific Publications, Oxford, 1968, pages 101-103.
The agrochemical formulations generally contain from 0.1 to 99% by weight, in particular from 0.1 to 95% by weight, of active compound of the formula (I).
In wettable powders the concentration of active compound is, for example, from about 10 to 90% by weight, the remainder to 100% by weight consisting of customary formulation constituents. In emulsifiable concentrates the concentration of active compound can be from about 1 to 90%, preferably from 5 to 80%, by weight.
Formulations in the form of dusts contain from 1 to 30% by weight of active compound, preferably most commonly from 5 to 20% by weight of active compound, while sprayable solutions contain from about 0.05 to 80%, preferably from 2 to 50%, by weight of active compound. In the case of water-dispersible granules, the content of active compound depends partly on whether the active compound is in lipuid or solid form and on the granulation auxiliaries, fillers, etc. that are used. In water-dispersible granules the content of active compound, for example, is between 1 and 95% by weight, preferably between 10 and 80% by weight.
In addition, said formulations of active compound may comprise the tackifiers, wetting agents, dispersants, emulsifiers, penetrants, preservatives, antifreeze agents, solvents, fillers, carriers, colorants, antifoams, evaporation inhibitors and pH and viscosity regulators which are customary in each case.
The compounds of the formula (I) or their salts can be used as such or combined in ~"'" the form of their preparations (formulations) with other pesticidally active compounds, such as, for example, insecticides, acaricides, nematicides, herbicides, fungicides, safeners, fertilizers andlor growth regulators, for example as finished formulations or tank mixes.
Suitable active compounds which can be combined with the active compounds according to the invention in mixed formulations or in a tank mix are, for example, known active compounds, as described, for example, in Weed Research 26, 441-(1986), or in "The Pesticide Manual", 10th edition, The British Crop Protection Council and the Royal Soc. of Chemistry, 1994, and in the literature cited therein.
For example, the following active compounds may be mentioned as herbicides or plant-growth ,,,~.~" regulators which are known from the literature and which can be combined with the compounds of the formula (I) (note: the compounds are either referred to by the "common name" in accordance with the International Organization for Standardization (ISO) or by the chemical names, if appropriate together with a customary code number):
acetochlor; acifluorfen(-sodium); aclonifen; AKH 7088, i.e. [[[1-[5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrophenyl]-2-methoxyethylidene]amino]oxy]acetic acid and its methyl ester; alachlor; alloxydim(-sodium); ametryn; amidochlor, amidosulfuron;
amitrol; AMS, i.e. ammonium sulfamate; anilofos; asulam; atrazine; azafenidin;
azimsulfuron (DPX-A8947); aziprotryn; barban; BAS 516 H, i.e. 5-fluoro-2-phenyl-4H-3,1-benzoxazin-4-one; beflubutamid; benazolin(-ethyl); benfluralin;
benfuresate;
bensulfuron(-methyl); bensulide; bentazone; benzobicyclone; benzofenap;
benzofluor;
benzoylprop(-ethyl); benzthiazuron; bialaphos; bifenox; bispyribac(-sodium);
bromacil;

bromobutide; bromofenoxim; bromoxynil; bromuron; buminafos; busoxinone;
butachlor; butafenacil; butamifos; butenachlor; buthidazole; butralin;
butroxydim;
butylate; cafenstrole (CH-900); carbetamide; cafentrazone(-ethyl) (ICI-A0051 );
caloxydim, CDAA, i.e. 2-chloro-N,N-di-2-propenylacetamide; CDEC, i.e. 2-chloroallyl 5 diethyldithiocarbamate; chlomethoxyfen; chloramben; chlorazifop-butyl;
chlormesulon (ICI-A0051 ); chlorbromuron; chlorbufam; chlorfenac; chlorflurecol-methyl;
chloridazon;
chlorimuron(-ethyl); chlornitrofen; chlorotoluron; chloroxuron; chlorpropham;
chlorsulfuron; chlorthal-dimethyl; chlorthiamid; chlortoluron, cinmethylin;
cinosulfuron;
clethodim; cinidon(-methyl), clefoxydim, clodinafop and its ester derivatives (for 10 example clodinafop-propargyl); clomazone; clomeprop; cloproxydim;
clopyralid;
clopyrasulfuron(-methyl); cloransulam(-methyl); cumyluron (JC 940); cyanazine;
cycloate; cyclosulfamuron (AC 104); cycloxydim; cycluron; cyhalofop and its ester derivatives (for example butyl-ester DEH-112); cyperquat; cyprazine;
cyprazole;
daimuron; 2,4-D; 2,4-DB; dalapon; desmedipham; desmetryn; di-allate; dicamba;
15 dichlobenil; dichlorprop; diclofop and its esters such as diclofop-methyl;
diclosulam, diethatyl(-ethyl); difenoxuron; difenzoquat; diflufenican; diflufenzopyr;
dimefuron;
dimepiperate; dimethachlor; dimethametryn; dimethenamid (SAN-582H);
dimethazone, dimexyflam, dimethipin; dimetrasulfuron, dinitramine; dinoseb; dinoterb;
diphenamid;
dipropetryn; diquat; dithiopyr; diuron; DNOC; eglinazine-ethyl; EL 77, i.e. 5-cyano-20 1-(1,1-dimethylethyl)-N-methyl-1 H-pyrazole-4-carboxamide; endothal;
epoprodan, EPTC; esprocarb; ethalfluralin; ethametsulfuron-methyl; ethidimuron; ethiozin;
ethofumesate; ethoxysulfuron, etobenzanid (NW 52); F5231, i.e. N-[2-chloro-4-fluoro-5-[4-(3-fluoropropyl)-4,5-dihydro-5-oxo-1 H-tetrazol-1-yl]-phenyl]ethanesulfonamide;
ethoxyfen and its esters (for example ethyl ester, HN-252); fenoprop; fenoxan, 25 fenoxaprop and fenoxaprop-P and their esters, for example fenoxaprop-P-ethyl and fenoxaprop-ethyl; fenoxydim; fentrazamide; fenuron; flamprop(-methyl or -isopropyl or -isopropyl-L); flazasulfuron; floazulate, florasulam; fluazifop and fluazifop-P and their esters, for example fluazifop-butyl and fluazifop-P-butyl; flucarbazone(-sodium);
fluchloralin; flumetsulam; flumeturon; flumiclorac(-pentyl); flumioxazin (S-482);
30 flumipropyn; fluometuron; fluorochloridone, fluorodifen; fluoroglycofen(-ethyl);
flupoxam (KNW-739); flupropacil CUBIC-4243); flupyrsulfuron(-methyl, or -sodium);
flurenol(-butyl); fluridone; flurochloridone; fluroxypyr(-meptyl);
flurprimidol, flurtamone;
fluthiacet(-methyl); fluthiamide; fomesafen; fosamine; furyloxyfen;
glufosinate(-ammonium); glyphosate(-isopropylammonium); halosafen; halosulfuron(-methyl) and its esters (for example the methyl ester, NC-319); haloxyfop and its esters;
haloxyfop-P (= R-haloxyfop) and its esters; hexazinone; imazamethabenz(-methyl);
imazapyr;
imazaquin and salts such as the ammonium salts; imazamethapyr; imazamox;
imazapic, imazethamethapyr; imazethapyr, imazosulfuron; indanofan; ioxynil;
isocarbamid; isopropalin; isoproturon; isouron; isoxaben; isoxachlortole;
isoxaflutole;
isoxapyrifop; karbutilate; lactofen; lenacil; linuron; MCPA; MCPB; mecoprop;
mefenacet; mefluidid; mesotrione; metamitron; metazachlor; methabenzthiazuron;
metham; methazole; methoxyphenone; methyldymron; metabenzuron, methobenzuron; metobromuron; (alpha-)metolachlor; metosulam (XRD 511 );
metoxuron; metribuzin; metsulfuron-methyl; MH; molinate; monalide;
monocarbamide dihydrogensulfate; monolinuron; monuron; MT 128, i.e. 6-chloro-N-(3-chloro-2-propenyl)-5-methyl-N-phenyl-3-pyridazinamine; MT 5950, i.e. N-[3-chloro-4-(1-methylethyl)-phenyl]-2-methylpentanamide; naproanilide; napropamide; naptalam;
NC
310, i.e. 4-(2,4-dichlorobenzoyl)-1-methyl-5-benzyloxypyrazole; neburon;
nicosulfuron;
nipyraclophen; nitralin; nitrofen; nitrofluorfen; norflurazon; orbencarb;
oryzalin;
oxadiargyl (RP-020630); oxadiazone; oxasulfuron; oxaciclomefone; oxyfluorfen;
paraquat; pebulate; pelargonic acid; pendimethalin; pentoxazone; perfluidone;
phenisopham; phenmedipham; picloram; picolinafen; piperophos; piributicarb;
pirifenop-butyl; pretilachlor; primisulfuron(-methyl); procarbazone(-sodium);
procyazine; prodiamine; profluralin; proglinazine(-ethyl); prometon;
prometryn;
propachlor; propanil; propaquizafop and its esters; propazine; propham;
propisochlor;
propyzamide; prosulfalin; prosulfocarb; prosulfuron (CGA-152005); prynachlor;
pyroflufen(-ethyl); pyrazolinate; pyrazon; pyrazosulfuron(-ethyl);
pyrazoxyfen;
pyribenzoxim; pyributicarb; pyridafoi; pyridate; pyriminobac(-methyl);
pyrithiobac(-sodium) (ICIH-2031 ); pyroxofop and its esters (for example propargyl ester);
quinclorac;
quinmerac; quinoclamine, quinofop and its ester derivatives, quizalofop and quizalofop-P and their ester derivatives, for example quizalofop-ethyl;
quizalofop-P-tefuryl and -ethyl; renriduron; rimsulfuron (DPX-E 9636); S 275, i.e. 2-[4-chloro-2-fluoro-5-(2-propynyloxy)phenyl]-4,5,6,7-tetrahydro-2H-indazole;
secbumeton;
sethoxydim; siduron; simazine; simetryn; SN 106279, i.e. 2-[[7-[2-chloro-4-(trifluoromethyl)phenoxy]-2-naphthalenyl]oxy]propanoic acid and its methyl ester;
sulcotrione; sulfentrazone (FMC-97285, F-6285); sulfazuron; sulfometuron(-methyl);
sulfosate (ICI-A0224); sulfosulfuron; TCA; tebutam (GCP-5544); tebuthiuron;
tepraloxydim; terbacil; terbucarb; terbuchlor; terbumeton; terbuthylazine;
terbutryn;

TFH 450, i.e. N,N-diethyl-3-[(2-ethyl-6-methylphenyl)sulfonyl]-1 H-1,2,4-triazole-1-carboxamide; thenylchlor (NSK-850); thiafluamide; thiazafluron;
thiazopyr (Mon-13200); thidiazimin (SN-24085); thifensulfuron(-methyl); thiobencarb;
tiocarbazil;
tralkoxydim; tri-allate; triasulfuron; triaziflam; triazofenamide; tribenuron(-methyl);
triclopyr; tridiphane; trietazine; trifluralin; triflusulfuron and esters (e.g. methyl ester, DPX-66037); trimeturon; tritosulfuron; tsitodef; vernolate; WL 110547, i.e. 5-phenoxy-1-[3-(trifluoromethyl)phenyl]-1H-tetrazole; UBH-509; D-489; LS 82-556; KPP-300;
NC-324; NC-330; KH-218; DPX-N8189; SC-0774; DOWCO-535; DK-8910; V-53482;
PP-600; MBH-001; KIH-9201; ET-751; KIH-6127 and KIH-2023.
,~ Of particular interest is the selective control of harmful plants in crops of useful and ornamental plants. Although the compounds (I) according to the invention have very good to satisfactory selectivity in a large number of crops, it is possible in principle that phytotoxicity in the crop plants can occur in some crops and, in particular, when the compounds (I) are mixed with other herbicides which are less selective. In this respect, combinations of the compounds (I) according to the invention which contain the compounds (I), or their combinations with other herbicides or pesticides, and safeners are of particular interest. The safeners, which are employed in such amounts that they act as antidotes, reduce the phytotoxic side effects of the herbicides/pesticides used, for example in economically important crops such as cereals (wheat, barley, rye, corn, rice, millet), sugar beet, sugar cane, oilseed rape, cotton and soya, preferably cereal.
,""" Suitable safeners for the compounds (I) and their combinations with other pesticides are, for example, the following groups of compounds:
a) Compounds of the type of dichlorophenylpyrazoline-3-carboxylic acid, preferably compounds such as ethyl 1-(2,4-dichlorophenyl)-5-(ethoxycarbonyl)-5-methyl-2-pyrazoline-3-carboxylate (S1-1 ) ("mefenpyr-diethyl", PM, pp. 781-782), and related compounds, as described in W O 91 /07874, b) Derivatives of dichlorophenylpyrazole carboxylic acid, preferably compounds such as ethyl 1-(2,4-dichlorophenyl)-5-methylpyrazole-3-carboxylate (S1-2), ethyl 1-(2,4-dichlorophenyl)-5-isopropylpyrazole-3-carboxylate (S1-3), ethyl 1-(2,4-dichlorophenyl)-5-( 1,1-dimethylethyl)pyrazole-3-carboxylate (S 1-4), ethyl 1-(2,4-dichlorophenyl)-5-phenylpyrazole-3-carboxylate (S1-5) and related compounds as described in EP-A-333 131 and EP-A-269 806.
c) Compounds of the type of the triazolecarboxylic acids, preferably compounds such as fenchlorazole(ethyl ester), i.e. ethyl 1-(2,4-dichlorophenyl)-5-trichloromethyl-(1H)-1,2,4-triazole-3-carboxylate (S1-6) and related compounds as described in EP-A-174 562 and EP-A-346 620.
d) Compounds of the type of the 5-benzyl- or 5-phenyl-2-isoxazoline-3-carboxylic acid, or the 5,5-Biphenyl-2-isoxazoline-3-carboxylic acid, preferably compounds such as ethyl 5-(2,4-dichlorobenzyl)-2-isoxazoline-3-carboxylate {S1-7) or ethyl 5-phenyl-2-isoxazoline-3-carboxylate (S1-8) and related compounds, as described in WO 91108202, or ethyl 5,5-Biphenyl-2-isoxazolinecarboxylate (S1-°~' 9) ("isoxadifen-ethyl") or its n-propyl ester (S1-10) or ethyl 5-(4-fluorophenyl)-5-phenyl-2-isoxazoline-3-carboxylate (S1-11), as described in the German patent application (V110-A-95/07897).
e) Compounds of the type of the 8-quinolineoxyacetic acid (S2), preferably 1-methylhex-1-yl (5-chloro-8-quinolineoxy) acetate (common name "cloquintocet-mexyl" (S2-1 ) (see PM, pp. 263-264) 1,3-dimethylbut-1-yl (5-chloro-8-quinolineoxy)acetate (S2-2), 4-allyloxybutyl (5-chloro-8-quinolineoxy)acetate (S2-3), 1-allyloxyprop-2-yl (5-chloro-8-quinolineoxy)acetate (S2-4), ethyl (5-chloro-8-quinolineoxy)acetate (S2-5), methyl (5-chloro-8-quinolineoxy)acetate (S2-6), ,,~., allyl (5-chloro-8-quinolineoxy)acetate (S2-7), 2-(2-propylideneiminoxy)-1-ethyl (5-chloro-8-quinolineoxy)acetate (S2-8), 2-oxoprop-1-yl (5-chloro-8-quinolineoxy)acetate (S2-9) and related compounds, as described in EP-A-86 750, EP-A-94 349 and EP-A-191 736 or EP-A-0 492 366.
f) Compounds of the type of the (5-chloro-8-quinolineoxy)malonic acid, preferably compounds such as diethyl (5-chloro-8-quinolineoxy)malonate, diallyl (5-chloro-8-quinolineoxy)malonate, methyl ethyl (5-chloro-8-quinolineoxy)malonate and related compounds, as described in EP-A-0 582 198.
g) Active compounds of the type of the phenoxyacetic or -propionic acid derivatives or the aromatic carboxylic acids, such as, for example, 2,4-dichlorophenoxyacetic acid (esters) (2,4-D), 4-chloro-2-methylphenoxypropionic esters (mecoprop), MCPA or 3,6-dichloro-2-methoxybenzoic acid (esters) (dicamba).
h) Active compounds of the type of the pyrimidines, which are used as soil-acting safeners in rice, such as, for example, "fenclorim" (PM, pp. 512-511 ) (= 4,6-dichloro-2-phenylpyrimidine), which is known as safener for pretilachlor in sown rice, i) Active compounds of the type of the dichloroacetamides, which are frequently used as pre-emergent safeners (soil-acting safeners), such as, for example, "dichlormid" (PM, pp. 363-364) (= N,N-diallyl-2,2-dichloroacetamide), "R-29148" (= 3-dichloroacetyl-2,2,5-trimethyl-1,3-oxazolidine from Stauffer), "benoxacor" (PM, pp. 102-103) (= 4-dichloroacetyl-3,4-dihydro-3-methyl-2H-1,4-benzoxazine), "PPG-1292" (= N-allyl-N-[(1,3-dioxolan-2-yl)methyl]dichloroacetamide from PPG
Industries), "DK-24" (= N-allyl-N-[(allylaminocarbonyl)methyl]dichloroacetamide from Sagro-Chem), "AD-67" or "MON 4660" (= 3-dichloroacetyl-1-oxa-3-aza-spiro[4,5]decane from Nitrokemia or Monsanto), "diclonon" or "BAS145138" or "l.AB145138" (= 3-dichloroacetyl-2,5,5-trimethyl-1,3-diazabicyclo[4.3.0]nonane from BASF' and "furilazol" or "MON 13900" (see PM, 637-638) (_ (RS)-3-dichloroacetyl-5-(2-",.., furyl)-2,2-dimethyloxazolidine) j) Active compounds of the type of the dichloroacetone derivatives, such as, for example, "MG 191" (CAS-Reg. No. 96420-72-3) (= 2-dichloromethyl-2-methyl-1,3-dioxolane from Nitrokemia), which is known as safener for corn, k) Active compounds of the type of the oxyimino compounds, which are known as seed dressings, such as, for example, "oxabetrinil" (PM, pp. 902-903) (_ (Z)-1,3-dioxolan-2-ylmethoxy-imino(phenyl)acetonitrile), which is known as seed dressing safener for millet against metolachlor damage, "fluxofenim" (PM, pp. 613-614) (= 1-(4-chlorophenyl)-2,2,2-trifluoro-l-ethanone O-(1,3-dioxolan-2-ylmethyl) oxime), which is known as seed dressing safener for millet against metolachlor damage, "cyometrinil" or "-CGA-43089" (PM, p. 1304) (_ (Z)-cyanomethoxyimino(phenyl)acetonitrile), which is known as seed dressing safener for millet against metolachlor damage, I) Active compounds of the type of the thiazolecarboxylic esters, which are known 5 as seed dressings, such as, for example, "flurazol" (PM, pp. 590-591 ) (= benzyl 2-chloro-4-trifluoromethyl-1,3-thiazole-5-carboxylate), which is known as seed dressing safener for millet against alachlor and metolachlor damage, m) Active compounds of the type of the naphthalenedicarboxylic acid derivatives, 10 which are known as seed dressings, such as, for example, "naphthalic anhydride" (PM, p. 1342) (= 1,8-naphthalenedicarboxylic anhydride), which is known as seed dressing safener for corn against thiocarbamate herbicide damage, n) Active compounds of the type of the chromanacetic acid derivatives, such as, 15 for example, "CL 304415" (CAS-Reg. No. 31541-57-8) (= 2-(4-carboxychroman-4-yl)acetic acid from American Cyanamid), which is known as safener for com against imidazolinone damage, o) Active compounds which, in addition to a herbidical action against harmful 20 plants, also have safener action in crop plants such as rice, such as, for example, ,,~.. "dimepiperate" or "MY-93" (PM, pp. 404-405) (= S-1-methyl-1-phenylethyl piperidine-1-thiocarboxylate), which is known as safener for rice against the herbicide molinate, 25 "daimuron" or "SK 23" (PM, p. 330) (= 1-(1-methyl-1-phenylethyl)-3-p-tolylurea), which is known as safener for rice against the herbicide imazosulfuron, "cumyluron" _ "JC-940" (= 3-(2-chlorophenylmethyl)-1-(1-methyl-1-phenylethyl)urea, see JP-A-60087254), which is known as safener for rice against damage by some herbicides, 30 "methoxyphenon" or "NK 049" (= 3,3'-dimethyl-4-methoxybenzophenone), which is known as safener for rice against damage by some herbicides, "CSB" (= 1-bromo-4-(chloromethylsulfonyl)benzene) (CAS-Reg. No. 54091-06-4 from Kumiai), which is known as safener against damage ~y some herbicides in rice p) N-Acylsulfonamides of the formula (S3) and salts thereof, R2 Ra R I O ~ / (R5)m ' -N
~ N \ / o (~) (R3)n as described in WO-A-97145016, ., q) Acylsulfamoylbenzoamides of the formula (S4), if appropriate also in salt form, O
_ O O
II \
\ ~ S N , (RS)m O
(R3)n Ra as described in the International Application No. PCT/EP98106097, and r) Compounds of the formula (S5), R' W
RZ ~ ~E)m Q2 /G (S5) as described in WO-A 98/13 361, including the stereoisomers and the salts used in agriculture.
Among the safeners mentioned, (S1-1) and (S1-9) and (S2-1), in particular (S1-1) and (S1-9), are of particular interest.
Some of the safeners are already known as herbicides and consequently show, in addition to the herbicidal action against harmful plants, also protective action in connection with crop plants.
The ratios by weight of herbicide (mixture) to safener generally depend on the application rate of the herbicide and the efficacy of the safener in question and can vary within wide limits, for example in the range from 200:1 to 1:200, preferably 100:1 to 1:100, in particular 20:1 to 1:20. Analogously to the compounds (I) or their mixtures, the safeners can be formulated with other herbicides/pesticides and be provided and used as ready-mix or tank mix with the herbicides.
For use, the herbicide or herbicide safener formulations which are present in commercially available form are, if appropriate, diluted in the customary manner, for example using water in the case of wettable powders, emulsifiable concentrates, dispersions and water-dispersible granules. Preparations in the form of dusts, granules ,.- for soil application or broadcasting and sprayable solutions are usually not further diluted with other inert substances prior to use.
The application rate of the compounds of the formula (I) required varies with the external conditions, such as temperature, humidity, the nature of the herbicide used and the like. It can vary within wide limits, for example between 0.001 and 10.0 kg/ha or more of active substance, but it is preferably between 0.005 and 5 kg/ha, in particular between 0.01 and 1 kg/ha of active substance.
In the examples below, the amounts (including percentages) are based on weight, unless specifically defined otherwise.
A. Chemical Examples (A1) 2-Amino-4-[1-(4-fluoro-3-methoxyphenyl)ethyl]amino-6-isopropyl-1,3,5-triazine 0.35 g (2.1 mmol) of 1-(4-fluoro-3-methoxyphenyl)ethylamine, 0.34 g (2.0 mmol) of 2-amino-4-chloro-6-isopropyl-1,3,5-triazine and 0.29 g (2.1 mmol) of potassium carbonate were initially charged in 20 ml of acetonitrile, and the mixture was heated at 79°C for 8 h. Using a rotary evaporator, the solvent was removed from the reaction mixture, and the residue was taken up in water and extracted with ethyl acetate. The combined organic phases were dried and filtered, and the solvent was distilled off using a rotary evaporator. The residue was purified chromatographically, giving 0.45 g (1.47 mmol, 73.7% yield) of the desired product as a solid of melting point 110-113°C.

(A2) 2-[1-(4-Chloro-3-methylphenyl)ethyl]amino-4-methyl-6-trichloromethyl-1,3,5-triazine 0.45 g (2.7 mmol) of 1-(4-chloro-3-methylphenyl)ethylamine and 0.87 g (2.7 mmol) of 2-methyl-4,6-bis(trichloromethyl)-1,3,5-triazine were initially charged in 20 ml of acetonitrile, and the mixture was heated at 70-75°C for 5 h. Using a rotary evaporator, the solvent was removed from the reaction mixture, the residue was taken up in ethyl acetate and water and the aqueous phase was then extracted twice with ethyl acetate.
The combined organic phases were dried and filtered, and the solvent was distilled off -. using a rotary evaporator. The residue was purified chromatographically, giving 0.62 g (1.63 mmol, 60.4% yield) of the desired produced as an oil.
(A3) Synthesis of 1-(3-bromo-4-fluorophenyl)ethylamine 9.5 g (43.8 mmol) of 3-bromo-4-fluoroacetophenone, 14.35 g (0.23 mol) of ammonium formate and 2.3 g (43.0 mmol) of 86% strength formic acid were heated at 160°C, with removal of water, for 5 h, and 0.75 g (14.0 mmol) of 86% strength formic acid were added after 3 h. The reaction mixture was taken up in water and diethyl ether, the aqueous phase was extracted twice with diethyl ether and the solvent was removed from the combined organic phases using a rotary evaporator. The residue was mixed with 10 ml of concentrated hydrochloric acid and heated under reflux for 2 h.
The content was taken up in water and the aqueous phase was extracted twice with ethyl acetate. With ice-cooling, the aqueous phase was made alkaline using 5 M
aqueous potassium hydroxide solution and again extracted twice with ethyl acetate. The two organic phases which were separated off last were combined and dried over magnesium sulfate, and the solvent was removed from the filtrate using a rotary evaporator. This gave 7.25 g (76% yield) of the desired product as an oil.
(A4) Synthesis of 2-amino-4-cyclobutyl-6-trichloromethyl-1,3,5-triazine At 0°C, a solution of 7.90 g (67 mmol) of cyclobutane carbonyl chloride in 25 ml of diethyl ether was added dropwise to a solution of 11.3 g (56 mmol) of trichloromethylimidoylguanide in 25 ml of diethyl ether. After 30 minutes at 0°C, 8.28 g (78 mmol) of triethylamine were added dropwise. The reaction mixture was then heated under reflux for 10 minutes. For work-up, the content was taken up in water, the aqueous phase was extracted with ethyl acetate, the combined organic phases were dried and the solvent was removed from the filtrate using a rotary evaporator.
Recrystallization gave 6 g (38.4% yield) of the desired product.
(A5) Synthesis of 2-amino-4-cyclobutyl-6-(3,5-dichlorobenzyl)amino-1,3,5-triazine 2.6 g (10 mmol) of 2-amino-4-cyclobutyl-6-trichloromethyl-1,3,5-triazine and 1.71 g (10 mmol) of 3,5-dichlorobenzylamine in 5 ml of N,N-dimethylformamide were heated "~ at 130°C for 2 h. The reaction mixture was fractionated chromatographically, giving 3.1 g (88.6% yield) of the desired product.
The compounds described in Tables 1 to 10 below are obtained according to or analogously to Examples A1 to A5 above or the methods described further above in a general manner. The abbreviations used in the tables are:
Me - CH3 - methyl (also in composed radicals, such as methylthio (SMe or -SMe or MeS-), methylsulfonyl (S02Me), dimethylamino (NMe2) etc.) ,,.... Ac - COCH3 - acetyl Bzl - CH2CgH5 - benzyl (n-)Bu - (n-)C4H9 - n-butyl t-Bu - tertiary butyl Et - C2H5 - ethyl (n-)Pr, i-Pr, c-Pr = (n-), i-, c-CgH~ = n-propyl, isopropyl and cyclopropyl, respectively (n-)Pen = n-pentyl Ph - phenyl Phys. data - Physical data; if a number is given, this number means the melting point in °C; "resin" or "oil" refers to the consistency of the non-crystalline compound obtained.
Table 1: Compounds of the formula (1 ) N N R
R6 (1) H
No. R3 R4 RS R6 R' R8 Phys.
data 5 CH3 i-Pr H Bzl H H

6 CH3 F H F H H Oil "" 8 CH3 Br H F H H

9 CH3 I H t-Bu H H

10 CH3 CH3 H OBzI H H

11 CH3 CF3 H OPh H H

12 CH3 OH H N02 H H Resin 13 CH3 OCH3 H NH2 H H Resin 14 CH3 CH20Me H C6H5 H H

15 CH3 F ~ H NHCOMe H H Resin 16 CH3 CI ', NHCHO H H Resin H

17 CH3 Br H N(S02Me)2H H Resin 18 CH3 I H NHSOZMe H H Resin ss No. R3 R4 R5 Rs R' Re Phys.
data 22 CH3 OCH3 H S02NHMe H H

26 CH3 Br H CH2NMe2 H H

30 CH3 CH2NMe2 H F H H

31 CH3 CH2S-Me H F H H

39 CH3 CH20CH3 H H N(CH3)2 H

42 CH3 Br H H S02CH3 H

46 CH3 H CH3 CI H H ~5 No. R3 R4 RS R6 R' Re Phys.
data 48 CH3 H CH3 F H H Oil 49 CH3 H OCH3 F H H Oil 51 CH3 H NH2 F H H Oil 52 CH3 H N(CH3)2 F H H

56 CH3 H N(S02Me)2F H H

56 CH3 H NHS02Me F H H

57 CH3 H SMe F H H

58 CH3 H SOMe F H H

6o CH3 H S02NHMe F H H

61 CH3 H S02NMez F H H

63 CH3 H NHCOMe SOZNH2 H H

,"", 64 CH3 H CH20CH3 F H H

66 CH3 H CH2NMe2 F H H

67 CH3 H F F H H Oil 68 CH3 H CI F H H Oil CH3 H Br F H H Resin 71 CH3 H F c-Pr H H Resin ?2 CH3 H F Bzl H H fiesin 73 CH3 H F CH=CH2 H H Resin 74 CH3 H F C---CH H H flesin No. R3 R4 RS Rs R' R8 Phys.
data 75 CH3 H F H F H Oil 76 CH3 F H CI F H Oil 77 CHFMe H OMe Br H H Resin 78 CHFMe H Me Br H H Resin 79 CHFMe H N02 Br H H Resin 8o CHFMe H NHZ Br H H Resin 81 CHFMe H N02 CI H H Resin r-82 CHFMe H NH2 CI H H Resin 83 CHFMe H OMe F H H Resin 84 CHFMe H N02 F H H Resin 86 CHFMe H NH2 F H H Resin 86 CHFMe OMe H F H H Resin 87 CHFMe F H F H H Resin 8B CHFMe F H H H F Resin 8A CHFMe H F H F H Resin 90 CHFMe H F F H H Resin 91 CHFMe H Me F H H Resin ,,.,..
92 CH3 H F CI H H Resin 93 CH3 H CH3 H N02 H Resin 94 CH3 H CF3 H NH2 H Resin CH3 H OH H N(CH3)2 H Resin 96 CH3 H OCH3 H NHCOCH3 H Resin 97 CH3 H CH3 H N02 H Resin 98 CH3 H CF3 H NH2 H Resin 99 CH3 H OH H N(CH3)z H Resin 100 CH3 H OCH3 H NHCOCH3 H Resin 101 CH3 H N02 H NHCHO H Resin 102 CH3 H NHZ H N(S02Me)2 H Resin No. R3 R4 _ Rs R6 R, RB Phys.
data 103 CH3 H N(CH3)2 H NHSOZMe H Resin 106 CH3 H N(SOZMe)2H Br H

107 CH3 H NHS02Me H I H

108 CH3 H SMe H CH3 H

109 CH3 H SOMe H CF3 H

,,..,. 110 CH3 H S02NH2 H OH H

111 CH3 H S02NHMe H OCH3 H

112 CH3 H S02NMe2 H SCH3 H

115 CH3 H F H S02NHMe H

116 CH3 H CI H S02NMe2 H

117 CH3 H Br H S02CH3 H

,"~",e 12D CH3 CH3 F H CI H

127 CH3 F H F F H Oil 6~
No. R3 R' RS Rs R' Rs Phys.
data 131 CH3 CH3 F F F CH3 Resin 135 CH3 H -CMe2-(CH2)2-CMe2- H H 64 136 CH3 H -(CH2)4- H H Resin 137 CH3 H -(CHZ)3- H H Resin 13B H H C! CI H H 186 13A CH3 H OCH3 OCH3 H H Resin 140 CH3 H CI H CH=CHEt H

141 CH3 H CI H C =CEt H

142 CH3 H CI H Ph H

144 CH3 H CI -(CH2)4- H

145 CH3 H CI -O(CH2)20- H Resin 146 CH3 H CI -OCH20- H Resin 147 CzH5 CH3 H CH3 H H

150 C2H5 H NMe2 CI H H

151 C2H5 H SOzCH3 CH3 H H

152 CH3 H CH3 Br H H

154 C~!-15 H CH3 F H H Resin 156 C~I-15 H CH3 CI H H

156 C~I-15 H CH3 Br H H

~5'l C~I-15 H CH3 I H H

158 C~hi5 H F F H H Resin No. R3 R4 RS Rs R' R8 Phys.
data 9 C~iS H F H F H Resin 180 c-Pr H OMe Br H H Resin 161 c-Pr H Me Br H H Resin 162 c-Pr H N02 Br H H Resin 163 c-Pr H NH2 Br H H Resin 164 c-Pr H N02 CI H H Resin 166 c-Pr H NH2 CI H H Resin 6 c-Pr H OMe F H H Resin 167 c-Pr H N02 F H H Resin 168 c-Pr H NH2 F H H Resin 169 c-Pr OMe H F H H Resin 170 c-Pr F H F H H Resin 171 c-Pr F H H H F Resin 172 c-Pr H Me F H H Resin 173 c-Pr H F F H H Resin 174 c-Pr H F H F H Resin 175 Me H CH3 CH20CH3 H H

176 Me H F CH20CH3 H H

177 Me H CI CH20CH3 H H

178 Me H Br CH20CH3 H H

9 Me H CH3 CHzSCH3 H H

180 Me H F CH2SCH3 H H

181 Me H CI CH2SCH3 H H

182 Me H Br CH2SCH3 H H

183 Me H CH3 CH2NMe2 H H

184 Me H F CH2NMe2 H H

X85 Me H CI CH2NMe2 H H

186 Me H Br CH2NMe2 H H

No. R3 R4 R5 Rs R' Rg Phys.
data 187 Me H CI CH3 H H

188 Me H Br CH3 H H

192 C2H5 H Br CH20CH3 H H

,~ 194 CZHS H F CH2SCH3 H H

196 C2H5 H Br CH2SCH3 H H

197 C2H5 H CH3 CH2NMe2 H H

198 CZHS H F CH2NMe2 H H

199 C2H5 H CI CH2NMe2 H H

200 C2H5 H Br CH2NMe2 H H

202 C2H5 H Br CH3 H H

Table 2: Compounds of the formula (2) C2Hs R4 R5 N N R
H N" ~ R6 N N
R g R7 No. R3 R4 R5 Rs R' R8 Phys.
data 208 CH3 i-Pr H CH2C6H5 H H

209 CH3 F H F H H Oil 211 CH3 Br H F H H

212 CH3 1 H C(CH3)3 H H

213 CH3 CH3 H OCH2CsH5 H H

214 CH3 CF3 H OCsHS H H

215 CH3 OH H N02 H H Resin 216 CH3 OCH3 H NH2 H H Resin 218 CH3 F H NHCOCH3 H H Resin 219 CH3 CI H NHCHO H H Resin 220 CH3 Br H N(S02CH3}2H H Resin 221 CH3 I H NHS02CH3 H H Resin No. R3 R4 RS R6 R' Rs Phys.
data 226 CH3 CH20Me H F H H

229 CH3 Br H CH2N(CH3)2H H

233 CH3 CH2NMe2 H F H H

234 CH3 CH2SMe H F H H

""'~"' 239 CH3 CF3 H H CH20CH3 H

242 CH3 CH20Me H H N(CH3)2 H Resin 245 CH3 Br H H S02CH3 H

No. R3 R4 R5 Rs R' R8 Phys.
data 251 CH3 H CH3 F H H Oil 254 CH3 H NH2 F H H Oil 256 CH3 H N(CH3)2 F H H

25-!CH3 H NHCHO F H H

258 CH3 H N(S02Me)2F H H

2a~ CH3 H NHSOZMe F H H

260 CH3 H SMe F H H

261 CH3 H SOMe F H H

263 CH3 H SOZNHMe F H H

a64 CH3 H S02NMe2 F H H

'"~' 266 CH3 H S02CH3 F H H

268 CH3 H CH2NMe2 F H H

27n CH3 H F F H H Oil 272 CH3 H Br F H H 47 274 CH3 H F c-Pr H H Resin No. R3 R4 RS Rs R' Re Phys.
data CH3 H F Bzl H H Resin 276 CH3 H F CH=CH2 H H Resin 2T7 CH3 H F C---CH H H Resin 278 CH3 H F H F H Oil z7g CH3 F H CI F H 85 2gp CHFMe H OMe Br H H Resin 281 CHFMe H Me Br H H Resin CHFMe H N02 Br H H Resin CHFMe H NH2 Br H H Resin 284 CHFMe H NOZ CI H H Resin 2g5 CHFMe H NH2 CI H H Resin 286 CHFMe H OMe F H H Resin 287 CHFMe H NOZ F H H Resin CHFMe H NHZ F H H Resin 2gg CHFMe OMe H F H H Resin 2gp CHFMe F H F H H Resin 291 CHFMe F H H H F Resin 292 CHFMe H F H F H Resin 293 CHFMe H F F H H Resin 294 CHFMe H Me F H H Resin 295 CH3 H F CI H H Resin 296 CH3 H CH3 H N02 H Resin 297 CH3 H CF3 H NH2 H Resin 298 CH3 H OH H N(CH3)2 H Resin 299 CH3 H OCH3 H NHCOCH3 H Resin 300 CH3 H N02 H NHCHO H Resin No. R3 R4 R5 R6 R' R8 Phys.
data 301 CH3 H NH2 H N(S02Me)2H Resin 302 CH3 H N(CH3)2 H NHS02CH3 H Resin 306 CH3 H N(S02Me)zH Br H

306 CH3 H NHS02Me H I H

307 CH3 H SMe H CH3 H

308 CH3 H SOMe H CF3 H

310 CH3 H SOZNHMe H OCH3 H

311 CH3 H SOZNMe2 H SCH3 H

315 CH3 H CI H S02NMe2 H

316 CH3 H Br H S02CH3 H

32'1 CH3 OCH3 CH3 H H F

32;i CH3 H F F F H

s$
No. R3 R4 RS R6 R' Re Phys.
data -(CH2)3- CH3 H Resin 336 CH3 H -C(CH3)2-(CH2)2-C(CH3)2- H H 64 336 CH3 H -(CH2)a- H H 60 338 CH3 H CI H CH=CHEt H

339 CH3 H CI H C ~CEt H

340 CH3 H CI H Ph H

342 CH3 H CI -(CH2)a- H

343 CH3 H CI -O(CH2)20- H

344 CH3 H CI -OCH20- H Resin 348 C2H5 H N(CH3)2 CI H H

360 Me H Me Br H H

351 Me H Me I H H

352 Et H Me F H H Resin No. R3 R4 Rs Rs R~ H8 Phys.
data 363 Et H Me CI H H

~4 Et H Me Br H H

356 Et H Me I H H

C~I-IS H F F H H Resin 367 C~I-15 H F H F H Resin c-Pr H OMe Br H H Resin 3gg c-Pr H Me Br H H Resin c-Pr H N02 Br H H Resin 361 c-Pr H NH2 Br H H Resin 362 c-Pr H N02 CI H H Resin c-Pr H NH2 CI H H Resin 364 c-Pr H OMe F H H Resin ~,5 c-Pr H N02 F H H Resin c-Pr H NH2 F H H Resin c-Pr OMe H F H H Resin ~g c-Pr F H F H H Resin '"~'' 369 c-Pr F H H H F Resin 37ipc-Pr H Me F H H Resin 371 c-Pr H F F H H Resin 372 c-Pr H F H F H Resin 373 Me H Me CH20Me H H

374 Me H F CH20Me H H

375 Me H CI CH20Me H H

3716Me H Br CH20Me H H

377 Me H CH3 CH2SMe H H

378 Me H F CH2SMe H H

No. R3 R4 RS R6 R~ Re phys.
data 379 Me H CI CH2SMe H H

380 Me H Br CH2SMe H H

381 Me H CH3 CH2NMe2 H H

382 Me H F CH2NMe2 H H

383 Me H CI CHzNMe2 H H

384 Me H Br CH2NMe2 H H

386 Me H CI CH3 H H

",a 386 Me H Br CH3 H H

3l37C2H5 H CH3 CHZOCH3 H H

3B0 C2H5 H Br CH20CH3 H H

3AfiC2H5 H CI CH2SCH3 H H

394 CpHg H Br CH2SCH3 H H

"""' 3A5 C2H5 H CH3 CH2NMe2 H H

3A6 CZHS H F CH2NMe2 H H

397 C2H5 H CI CH2NMe2 H H

3AE C2H5 H Br CH2NMe2 H H

400 C2H5 H Br CH3 H H

Table 3: Compounds of the formula (3) N ~ N R3 R6 (3) H o8 No. R3 R4 R5 Rs R' Re Phys.
" data 403 CH3 CF3 H F H H Oil 406 CH3 i-Pr2 H CH2CeH5 H H

407 CH3 F H F H H Oil 409 CH3 Br H F H H

,,,.", 410 CH3 I H C(CH3)3 H H

413 CH3 OH H NOZ H H Resin 414 CH3 OCH3 H NHz H H Resin 415 CH3 CH20Me CsHS H H
' H

416 CH3 F H NHCOCH3 H H Resin 417 CH3 CI H NHCHO H H Resin 418 CH3 Br I H N(S02Me)2H H Resin ~

419 CH3 I ; H NHS02CH3 H H Resin No. R3 R4 R5 R6 R' Re Phys.
data 424 CH3 CH20Me H F H H

427 CH3 Br H CH2NMe2 H H

42B CH3 1 H CHzSCH3 H H

431 CH3 CH2NMe2 H F H H

432 CH3 CH2SMe H F H H

~ 436 CH3 CH3 H H CH3 H

440 CH3 CH20Me H H N(CH3)2 H Resin 443 CH3 Br H H SOZCH3 H

No. R3 R4 R5 R6 R' R$ Phys.
data 447 CH3 H CH3 CI H H Oil 449 CH3 H CH3 F H H Oil 452 CH3 H NH2 F H H Oil 453 CH3 H N(CH3)2 F H H

456 CH3 H N(S02Me)2F H H

458 CH3 H SMe F H H

45g CH3 H SOMe F H H

'~'~ 462 CH3 H S02NMe2 F H H

466 CH3 H CH2NMe2 F H H

46B CH3 H F F H H Oil 470 CH3 H Br F H H Oil No. R3 R4 RS Rs R' Re Phys.
data 472 CH3 H F c-Pr H H Resin 473 CH3 H F Bzl H H Resin 474 CH3 H F CH=CHZ H H Resin 4~ CH3 H F C---CH H H Resin 476 CH3 H F H F H Oil 477 CH3 F H CI F H Oil 47g CHFMe H OMe Br H H Resin ' 47g CHFMe H Me Br H H Resin 480 CHFMe H N02 Br H H Resin CHFMe H NH2 Br H H Resin 482 CHFMe H NOz CI H H Resin 483 CHFMe H NH2 CI H H Resin 484 CHFMe H OMe F H H Resin 485 CHFMe H N02 F H H Resin CHFMe H NH2 F H H Resin 487 CHFMe OMe H F H H Resin ,.~.. a~g CHFMe F H F H H Resin 489 CHFMe F H H H F Resin 490 CHFMe H F H F H Resin 491 CHFMe H F F H H Resin 492 CHFMe H Me F H H Resin qg3 CH3 H F CI H H Resin 494 CH3 H CH3 H NOZ H Resin 495 CH3 H CF3 H NH2 H Resin 496 CH3 H OH H N(CH3)2 H Resin 497 CH3 H OCH3 H NHCOCH3 H Resin No. R3 R4 R5 R6 R' R$ Phys.
data 498 CH3 H N02 H NHCHO H Resin 499 CH3 H NH2 H N(S02Me)2H Resin 500 CH3 H N(CH3)2 H NHS02Me H Resin 503 CH3 H N(S02Me)2H Br H

509 CH3 H S02NMez H SCH3 H

512 CH3 H F H S02NHMe H

513 CH3 H CI H S02NMe2 H

'~ 514 CH3 H Br H S02CH3 H

No. R3 R4 R5 R6 R' R8 Phys.
data 524 CH3 F H F F H Oil 532 CH3 H -(CH2)4- H H Resin 533 CH3 H CI H CH=CHEt H

534 CH3 H CI H C =CEt H

535 CH3 H CI H CsHs H

537 CH3 H CI -(CHZ)a- H

538 CH3 H CI -O(CH2)20- H

"' 540 C2H5 CH3 H CH3 H H

542 CZH5 CH3 H CI H H Resin 543 C2H5 H N(CH3)2 CI H H Resin 544 C2H5 H S02CH3 CH3 H H Resin 545 Me H Me Br H H

546 Me H Me I H H

547 Et H Me F H H fiesin 548 Et H Me CI H H

549 Et H Me Br H H

No. R3 R4 R5 R6 R' R8 Phys.
data 560 Et H Me 1 H H

C~I-i5 H F F H H Resin 562 C~I-IS H F H F H Resin c-Pr H OMe Br H H Resin c-Pr H Me Br H H Resin c-Pr H N02 Br H H Resin c-Pr H NH2 Br H H Resin 557 c-Pr H N02 CI H H Resin c-Pr H NH2 CI H H Resin c-Pr H OMe F H H Resin c-Pr H N02 F H H Resin c-Pr H NH2 F H H Resin c-Pr OMe H F H H Resin c-Pr F H F H H Resin c-Pr F H H H F Resin c-Pr H Me F H H Resin ~""w ~ c-Pr H F F H H Resin c-Pr H F H F H Resin 568 Me H Me CH20CH3 H H

569 Me H F CHZOCH3 H H

51n Me H CI CH20CH3 H H

571 Me H Br CH20CH3 H H

6T2 Me H CH3 CH2SCH3 H H

573 Me H F CH2SCH3 H H

574 Me H CI CH2SCH3 H H

575 Me H Br CH2SCH3 H H

No. R3 R4 R5 R6 R' R8 Phys.
data 576 Me H CH3 CHZNMe2 H H

5?T Me H F CH2NMe2 H H

578 Me H CI CH2NMe2 H H

579 Me H Br CHZNMe2 H H

590 Me H CI CH3 H H

5s1 Me H Br CH3 H H

"~ 583 C2H5 H F CH20CH3 H H

585 C2H5 H Br CH20CH3 H H

589 CZHS H Br CH2SCH3 H H

56o CZHS H CH3 CH2NMe2 H H

591 CZHS H F CHZNMe2 H H

"""' See C2H5 H CI CHZNMe2 H H

5A3 C2H5 H Br CH2NMe2 H H

595 C2H5 H Br CH3 H H

yes CZHS H F CH3 H H

Table 4: Compounds of the formula (4) N ~ N R3 R6 (4) H o s R7 _ Rs R4 - R5 Rs R' Ra Phys.
No. data 600 CH3 OCH3 H F H H Oil 601 CH3 i-Pr H CHzCeHS H H

60r2 CH3 F H F H H Oil 607 CH3 CH3 H OCH2CeH5 H H

608 CH3 CF3 H OCsHS H H

609 CH3 OH H NOZ H H Resin 610 CH3 OCH3 H NHZ H H Resin 611 CH3 CHZOMe H CsHS H H

612 CH3 F H NHCOCH3 H H Resin 613 CH3 CI H NHCHO H H Resin 614 CH3 Br H N(SOZCH3)2H H Resin No. R3 R4 RS R6 R' R8 Phys.
data 615 CH3 I H NHS02CH3 H H Resin 620 CH3 CH20Me H F H H

6zi CH3 Br H CH2N(CH3)2H H

624 CH3 I H CHzSCH3 H H

627 CH3 CH2NMe2 H F H H

628 CH3 CHZSMe H F H H

'"'"' 631 CH3 F CF3 H H H

636 CH3 CH20Me H H N(CH3)2 H Resin 639 CH3 Br H H S02CH3 H

No. R3 R4 RS R6 R' RB Phys.
data 643 CH3 H CH3 CI H H Oil '~ 648 CH3 H NH2 F H H Oil 649 CH3 H N(CH3)2 F H H

662 CH3 H N(SOZCH3)2F H H

668 CH3 H S02N(CH3)2F H H

662 CH3 H CH2N(CH3)2F H H

666 CH3 H CI F H H Oil 666 CH3 H Br F H H 61 No. R3 R4 R5 Rs R' RB Phys.
data Egg CH3 H F c-Pr H H Resin Egg CH3 H F Bzl H H Resin 67p CH3 H F CH=CH2 H H Resin 671 CH3 H F C---CH H H Resin CH3 H F H F H Oil g73 CH3 F H CI F H Oil _ 674 CHFMe H OMe Br H H Resin CHFMe H Me Br H H Resin CHFMe H N02 Br H H Resin 677 CHFMe H NH2 Br H H Resin 67g CHFMe H N02 CI H H Resin CHFMe H NH2 CI H H Resin CHFMe H OMe F H H Resin CHFMe H N02 F H H Resin 682 CHFMe H NH2 F H H Resin "" 683 CHFMe OMe H F H H Resin CHFMe F H F H H Resin 686 CHFMe F H H H F Resin Egg CHFMe H F H F H Resin 687 CHFMe H F F H H Resin CHFMe H Me F H H Resin Egg CH3 H F CI H H Resin 690 CH3 H CH3 H N02 H Resin CH3 H CF3 H NHz H Resin 692 CH3 H OH H N(CH3)2 H Resin No. R3 R4 R5 R6 R' Rg Phys.
data 6g3 CH3 H OCH3 H NHCOCH3 H Resin 6A4 CH3 H N02 H NHCHO H Resin 6A5 CH3 H NH2 H N(S02CH3)2H Resin 696 CH3 H N(CH3)2 H NHS02CH3 H Resin 6A9 CH3 H N(S02CH3)2H Br H

70Ci CH3 H S02NH2 H OH H

706 CH3 H SOZN(CH3)2H SCH3 H

'"~ 709 CH3 H CI H S02N(CH3)2H

710 CH3 H Br H S02CH3 H

714 CH3 OCH3 CI H F H Oil 718 CH3 CI H ~ F OCH3 H Oil No. R3 R4 RS R6 R' Re Phys.
data 72a CH3 F H F F H

7?2 CH3 F F CI CHI H

728 CH3 H CI H CH=CHEt H

729 CH3 H CI H C =CEt H

730 CH3 H CI H CsHS H

732 CH3 H CI -(CH2)4- H

733 CH3 H CI -O(CH2)20- H

"~ 735 Et CH3 H CH3 H H

736 Et F H CH3 H H

737 Et CH3 H CI H H

738 Et H N(CH3)2 CI H H Resin 739 Et H S02CH3 CH3 H H

740 Me H Me Br H H

741 Me H Me I H H

742 Et H Me F H H Resin 743 Et H Me CI H H

744 Et H Me Br H H

No. R3 R4 RS Rs R' R8 Phys.
data 745 Et H Me I H H

746 C~I-IS H F F H H Resin 747 C~I-15 H F H F H Resin 748 c-Pr H OMe Br H H Resin 749 c-Pr H Me Br H H Resin 750 c-Pr H N02 Br H H Resin 751 c-Pr H NH2 Br H H Resin "~ 752 c-Pr H N02 CI H H Resin 753 c-Pr H NH2 CI H H Resin '754 c-Pr H OMe F H H Resin 756 c-Pr H N02 F H H Resin 756 c-Pr H NH2 F H H Resin 757 c-Pr OMe H F H H Resin 758 c-Pr F H F H H Resin 7gg c-Pr F H H H F Resin 760 c-Pr H Me F H H Resin 761 c-Pr H F F H H Resin 762 c-Pr H F H F H Resin 763 Me H Me CH20CH3 H H

764 Me H F CH20CH3 H H

766 Me H CI CH20CH3 H H

766 Me H Br CH20CH3 H H

767 Me H CH3 CH2SCH3 H H

768 Me H F CH2SCH3 H H

769 Me H CI CH2SCH3 H H

770 Me H Br CH2SCH3 H H

No. R3 R4 R5 R6 R' RB Phys.
data 771 Me H CH3 CH2N(CH3)2H H

772 Me H F CH2N(CH3)2H H

773 Me H CI CH2N(CH3)2H H

774 Me H Br CH2N(CH3)2H H

775 Me H CI CH3 H H

776 Me H Br CH3 H H

777 Et H CH3 CH20CH3 H H

778 Et H F CH20CH3 H H

779 Et H CI CH20CH3 H H

780 Et H Br CH20CH3 H H

781 Et H CH3 CH2SCH3 H H

782 Et H F CH2SCH3 H H

783 Et H CI CH2SCH3 H H

784 Et H Br CH2SCH3 H H

786 Et H CH3 CHzN(CH3)ZH H

786 Et H F CH2N(CH3)2H H

''~ 787 Et H CI CH2N(CH3)2H H

788 Et H Br CHZN(CH3)2H H

789 Et H CI CH3 H H

790 Et H Br CH3 H H

T91 Et H F CH3 H H

Table 5: Compounds of the formula (5) F

N ~ N R3 R 6 (5) H Rg No. R3 R R5 R6 R' RS Phys.
,,~" data 79a CH3 CF3 H F H H 68 796 CH3 OCH3 H F H H Oil 796 CH3 i-Pr H CH2CsH5 H H

799 CH3 Br H F H H

800 CH3 I H C(CH3)3 H H

ern CH3 CH3 H OCH2C6H5 H H

802 CH3 CF3 H OCsHS H H

80(3 CH3 OH H N02 H H

805 CH3 CH20Me H C6H5 H H

808 CH3 Br H N(S02Me)2 H H

No. R3 R RS Rs R' R8 Phys.
data 814 CH3 CHZOMe H F H H

817 CH3 Br H CH2NMeZ H H

821 CH3 CHZNMe2 H F H H

822 CH3 CH2SMe H F H H

82<i CH3 CH3 F H H H

-" 826 CH3 CH3 H H CH3 H

830 CH3 CH20Me H H N(CH3)2 H Resin 833 CH3 Br H H S02CH3 H

No. R3 R4 RS R6 R' Re Phys.
data 840 CH3 H OCH3 F H H Oil 842 CH3 H NH2 F H H Oil 843 CH3 H N(CH3)2 F H H

846 CH3 H N(S02Me)2F H H

852 CH3 H S02NMe2 F H H

85,3 CH3 H S02CH3 F H H

856 CH3 H CH2NMe2 F H H

869 CH3 H CI F H H Oil 860 CH3 H Br F H H 62 No. R3 R4 R5 R6 R' R8 Phys.
data 862 CH3 H F c-Pr H H Resin 863 CH3 H F Bzl H H Resin 864 CH3 H F CH=CH2 H H Resin 866 CH3 H F C---CH H H Resin 866 CH3 H F H F H Oil 867 CH3 F H CI F H Oil ,....
868 CFHMe H OMe Br H H Resin 869 CFHMe H Me Br H H Resin 8710 CFHMe H N02 Br H H Resin 87~ CFHMe H NH2 Br H H Resin 872 CFHMe H N02 CI H H Resin 873 CFHMe H NH2 CI H H Resin 874 CFHMe H OMe F H H Resin 875 CFHMe H NO2 F H H Resin 876 CFHMe H NH2 F H H Resin 877 CFHMe OMe H F H H Resin 878 CFHMe F H F H H Resin 879 CFHMe F H H H F Resin 880 CFHMe H F H F H Resin 881 CFHMe H F F H H Resin 882 CFHMe H Me F H H Resin 883 CH3 H F CI H H Resin 884 CH3 H CH3 H N02 H Resin 8~ CH3 H CF3 H NH2 H Resin 886 CH3 H OH H N(CH3)2 H Resin 887 CH3 H OCH3 H NHCOCH3 H Resin No. R3 R4 RS R6 R' R$ Phys.
data 888 CH3 H N02 H NHCHO H Resin 889 CH3 H NH2 H N(S02CH3)2H Resin 880 CH3 H N(CH3)2 H NHS02CH3 H Resin 89Ci CH3 H N(S02Me)2H Br H

~4 CH3 H NHS02CH3 H I H

eAB CH3 H S02NHCH3 H OCH3 H

CH3 H SOZNMe2 H SCH3 H

90o CH3 H S02CH3 H SOCH3 H

903 CH3 H CI H S02N(CH3)ZH

904 CH3 H Br H S02CH3 H

No. R3 R4 RS R6 R' R$ Phys.
data 922 CH3 H CI H CH=CHet H

92;3 CH3 H CI H C =CEt H

9p4 CH3 H CI H C6H5 H

9~i CH3 H CI H CN H

926 CH3 H CI -(CH2)4- H

9127 CH3 H CI -O(CH2}20- H

928 CH3 H CI -OCH20- H Resin 931 CzHs CH3 H CI H H

902 CZHS H N(CH3)2 CI H H

93;i C2H5 H SOZCH3 CH3 H H

934 Me H Me Br H H

936 Me H Me I H H

906 Et H Me F H H Resin 937 Et H Me CI H H

938 Et H Me Br H H

939 Et H Me I H H

No. R3 R4 RS Rs R' R8 Phys.
data 940 C~I-IS H F F H H Resin 941 CzHS H F H F H Resin 942 c-Pr H OMe Br H H Resin 943 c-Pr H Me Br H H Resin 944 c-Pr H N02 Br H H Resin 945 c-Pr H NH2 Br H H Resin 946 c-Pr H N02 CI H H Resin 947 c-Pr H NH2 Cl H H Resin 948 c-Pr H OMe F H H Resin 949 c-Pr H N02 F H H Resin 950 c-Pr H NHZ F H H Resin 951 c-Pr OMe H F H H Resin 952 c-Pr F H F H H Resin 953 c-Pr F H H H F Resin 954 c-Pr H Me F H H Resin 955 c-Pr H F F H H Resin 956 c-Pr H F H F H Resin 957 Me H Me CH20CH3 H H

968 Me H F CH20CH3 H H

959 Me H CI CH20CH3 H H

960 Me H Br CH20CH3 H H

961 Me H CH3 CHZSCH3 H H

962 Me H F CH2SCH3 H H

963 Me H CI CH2SCH3 H H

964 Me H Br CH2SCH3 H H

966 Me H CH3 CH2NMe2 H H

No. R3 R' R5 R6 R' R8 Phys.
data 966 Me H F CH2NMe2 H H

967 Me H CI CH2NMez H H

968 Me H Br CH2NMe2 H H

968 Et H CI CH3 H H

970 Me H Br CH3 H H

9r71 Et H CH3 CH20CH3 H H

972 Et H F CH20CH3 H H

9T3 Et H CI CH20CH3 H H

974 Et H Br CH20CH3 H H

975 Et H CH3 CH2SCH3 H H

976 Et H F CH2SCH3 H H

977 Et H CI CH2SCH3 H H

978 Et H Br CH2SCH3 H H

979 Et H CH3 CH2NMe2 H H

980 Et H F CH2NMe2 H H

981 Et H CI CH2NMe2 H H

982 Et H Br CH2NMe2 H H

983 Et H CI CH3 H H

984 Et H Br CH3 H H

98,5 Et H F CH3 H H

Table 6: Compounds of the formula (6) F

N ~ N R3 H N' _N' _ R6 (6) N
No. R3 R4 R5 R6 R' R8 Phys.
data 989 CH3 OCH3 H F H H Oil 990 CH3 i-Pr H CHZCBHS H H

991 CH3 F H F H H Oil 99;i CH3 Br H F H H

~"' 994 CH3 I H C(CH3)3 H H
l 997 CH3 OH H NOZ H H Resin 998 CH3 OCH3 H NHZ H H Resin 999 CH3 CHZOMe H C6H5 H H

1000 CH3 F H NHCOCH3 H H Resin I

1001 CH3 CI H NHCHO H H Resin 1002 CH3 Br H N(S02Me)2H H Resin 1003 CH3 I H NHS02CH3 H H Resin No. R3 R4 R5 R6 R' Re Phys.
data 1008 CH3 CH20Me H F H H

1011 CH3 Br H CH2NMe2 H H

1015 CH3 CH2NMe2 H F H H

1016 CH3 CH2SMe H F H H

10e4 CH3 CH20Me H H N(CH3)2 H Resin 1027 CH3 Br H H S02CH3 H

No. R3 R RS Rs R' R8 Phys.
data 1033 CH3 H CH3 F H H Oil 1034 CH3 H OCH3 F H H Oil 1036 CH3 H NH2 F H H Oil 1037 CH3 H N(CH3)2 F H H

1040 CH3 H N(S02Me)2F H H

1042 CH3 H SMe F H H

1043 CH3 H SOMe F H H

1046 CH3 H S02NMe2 F H H

1050 CH3 H CH2NMe2 F H H

1053 CH3 H CI F H H Oil 1064 CH3 H Br F H H 132 No. R3 R R5 R6 R' Re Phys.
data X056 CH3 H F c-Pr H H Resin 1057 CH3 H F CHzC6H5 H H Resin X058 CH3 H F CH=CH2 H H Resin CH3 H F C---CH H H Resin 1062 CHFMe H OMe Br H H Resin 1063 CHFMe H Me . Br H H Resin 1064 CHFMe H N02 Br H H Resin 1066 CHFMe H NH2 Br H H Resin 1066 CHFMe H N02 CI H H Resin 1067 CHFMe H NH2 CI H H Resin 1068 CHFMe H OMe F H H Resin 1069 CHFMe H N02 F H H Resin 1070 CHFMe H NHZ F H H Resin 1071 CHFMe OMe H F H H flesin ~0'T2 CHFMe F H F H H Resin 1073 CHFMe F H H H F Resin 1074 CHFMe H F H F H Resin t075 CHFMe H F F H H Resin 1076 CHFMe H Me F H H Resin 1077 CH3 H F CI H H Resin 1078 CH3 H CH3 H N02 H Resin CH3 H CF3 H NH2 H Resin 1060 CH3 H OH H N(CH3)2 H Resin CH3 H OCH3 H NHCOCH3 H Resin No. R3 R4 RS R6 R' RB Phys.
data 1082 CH3 H NOZ H NHCHO H Resin 1083 CH3 H NH2 H N(S02Me)2H Resin 1084 CH3 H N(CH3)2 H NHS02CH3 H Resin 1087 CH3 H N(S02Me)2H Br H

1089 CH3 H SMe H ~ CH3 H

1090 CH3 H SOMe H CF3 H

1093 CH3 H SOZNMe2 H SCH3 H

109~t CH3 H S02CH3 H SOCH3 H

1097 CH3 H CI H S02NMe2 H

loeB CH3 H Br H SOZCH3 H

1099 CH3 H I H C~HS H

11~ CH3 OCH3 CI H F H Oil No. R3 R4 R5 Rs R' R8 Phys.
data 1116 H H CI CI H H Resin 1117 CH3 H -(CHZ)3- H H Resin 1118 CH3 H CI H CH=CHEt H

1119 CH3 H CI H C =CEt H

1120 CH3 H CI H CsHs H

1122 CH3 H CI -(CH2)4- H

1123 CH3 H CI -O(CHZ)20- H

1128 C2H5 H N(CH3)2 CI H H

1130 Me H Me Br H H

1131 Me H Me I H H

1132 Et H Me F H H Resin 1133 Et H Me CI H H

No. R3 R4 RS R6 R' R8 Phys.
data 1134 E H Me Br H H

Et H Me I H H

1136 C~I-IS H F F H H Resin 1137 CzHS H F H F H Resin t138 c-Pr H OMe Br H H Resin 1139 c-Pr H Me Br H H Resin 1140 c-Pr H N02 Br H H Resin 1141 c-Pr H NH2 Br H H Resin 1142 c-Pr H N02 CI H H Resin 1143 c-Pr H NH2 CI H H Resin 1144 c-Pr H OMe F H H Resin 1145 c-Pr H N02 F H H Resin 1146 c-Pr H NH2 F H H Resin 1147 c-Pr OMe H F H H Resin 1148 c-Pr F H F H H Resin 1149 c-Pr F H H H F Resin 1150 c-Pr H Me F H H Resin 1151 c-Pr H F F H H Resin 1152 c-Pr H F H F H Resin 1153 Me H Me CH20CH3 H H

1154 Me H F CHZOCH3 H H

1155 Me H CI CH20CH3 H H

1156 Me H Br CHZOCH3 H H

1157 Me H CH3 CH2SCH3 H H

1158 Me H F CH2SCH3 H H

1159 Me H CI CH2SCH3 H H

No. R3 R4 RS R6 R' R8 Phys.
data 1160 Me H Br CH2SCH3 H H

1161 Me H CH3 CH2NMe2 H H

1162 Me H F CH2NMe2 H H

1163 Me H CI CHZNMe2 H H

1164 Me H Br CH2NMe2 H H

Me H CI CH3 H H

1166 Me H Br CH3 H H

1170 C2H5 H Br CH20CH3 H H

1174 C2H5 H Br CH2SCH3 H H

1175 C2H5 H CH3 CH2NMe2 H H

1176 CZHS H F CH2NMe2 H H

1177 C2H5 H CI CHZNMe2 H H

1178 C2H5 H Br CH2NMe2 H H

1180 C2H5 H Br CH3 H H

Table 7: Compounds of the formula (7) N ~ N R3 R6 (7) No. R3 R4 R5 R6 R' R$ Phys.
'""~' data 1182 CH3 CH3 H F H H Resin 1186 CH3 i-Pr H CH2CsH5 H H

.. 1189 CH3 Br H F H H

1190 CH3 I H i-Pr H H

1191 CH3 CH3 H OCH2Ph H H

1192 CH3 CF3 H OPh H H

1193 CH3 OH H NOz H H Resin 1194 CH3 OCH3 H NHZ H H Resin 1195 CH3 CHzOMe H Ph H H
I

1196 CH3 F H NHCOMe H H Resin 1197 CH3 CI H NHCHO H H Resin 1198 CH3 Br H N(S02Me)2H H Resin ~

No. R3 R4 RS R6 R' RB Phys.
data 1199CH3 I H NHS02Me H H Resin 1200CH3 CH3 H SMe H H

1201CH3 CF3 H SOMe H H

120ciCH3 OCH3 H SOZNHMe H H

1204CH3 CH20Me H F H H

1207CH3 Br H CH2NMe2 H H

1211CH3 CH2NMe2 H F H H

1212CH3 CH2SMe H F H H

1220CH3 CH20Me H H N(CH3)2 H Resin 1223CH3 Br H H S02CH3 H

No. R3 R4 RS R6 R' Re Phys.
data 1233 CH3 H N(CH3)2 F H H

1236 CH3 H N(S02CH3)2F H H

1238 CH3 H SMe F H H

1239 CH3 H SOMe F H H

1240 CH3 H SOzNH2 F H H

"~ 1241 CH3 H SOZNHCH3 F H H

1242 CH3 H S02N(CH3)2F H H

1246 CH3 H CHZN(CH3)2F H H

1250 CH3 H Br F H H

No. R3 R4 RS R6 R' R$ Phys.
data 1252 CH3 H F c-Pr H H Resin 1253 CH3 H F CH2CsH5 H H Resin 1254 CH3 H F CH=CH2 H H Resin 1256 CH3 H F C---CH H H Resin 1256 CH3 H F H F H Oil 1257 CH3 F H CI F H Oil 1258 CHFMe H OMe Br H H Resin 1299 CHFMe H Me Br H H Resin 1260 CHFMe H N02 Br H H Resin 1261 CHFMe H NH2 Br H H Resin 1262 CHFMe H N02 CI H H Resin 128'iCHFMe H NH2 CI H H Resin 1264 CHFMe H OMe F H H Resin 1266 CHFMe H N02 F H H Resin 1286 CHFMe H NHZ F H H Resin 1267 CHFMe OMe H F H H Resin 1268 CHFMe F H F H H Resin 1269 CHFMe F H H H F Resin 12'l~CHFMe H F H F H Resin 1271 CHFMe H F F H H Resin 1272 CHFMe H Me F H H Resin 1273 CH3 H F CI H H Resin 1274 CH3 H CH3 H NOZ H Resin 1275 CH3 H CF3 H NH2 H Resin 1276 CH3 H OH H N(CH3)2 H Resin No. R3 R4 RS R6 R' R8 Phys.
data 1277 CH3 H OCH3 H NHCOCH3 H Resin 1278 CH3 H N02 H NHCHO H Resin 1279 CH3 H NH2 H N(SOZCH3)2 H Resin 1280 CH3 H NMe2 H NHS02CH3 H Resin 1283 CH3 H N(S02Me)2 H Br H

1284 CH3 H NHSOzMe H I H

1286 CH3 H SMe H CH3 H

1286 CH3 H SOMe H CF3 H

1288 CH3 H S02NHMe H OCH3 H

1289 CH3 H S02NMe2 H SCH3 H

1292 CH3 H F H SOzNHCH3 H

1293 CH3 H CI H S02N(CH3)2 H

1294 CH3 H Br H S02CH3 H

No. R3 R4 RS R6 R' Re Phys.
data 1312 CH3 H CI H GH=CHEt H

1313 CH3 H CI H C =CEt H

1316 CH3 H CI -(CH2)a-1317 CH3 H CI -O(CH2)20-"w 1319 C2H5 CH3 H CH3 H H Resin 1320 C2H5 F H CH3 H H Resin 1321 C2H5 CH3 H CI H H Resin 1322 C2H5 H N(CH3)2 CI H H Resin 1323 C2H5 H S02CH3 CH3 H H Resin 1324 Me H CHI Br H H

1325 Me H CHI I H H

1326 Et H CHI F H H Resin 1327 Et H CHI CI H H

1328 Et H CHI Br H H

No. R3 R4 R5 R6 R' R8 Phys.
data 1329 Et H CHI I H H

1330 Et H CH3 CH20CH3 H H

1331 CzFiS H F F H H Resin 1332 C~i-15 H F H F H Resin 1333 c-Pr H OMe Br H H Resin 1334 c-Pr H Me Br H H Resin 1336 c-Pr H N02 Br H H Resin 1336 c-Pr H NH2 Br H H Resin 1337 c-Pr H N02 CI H H Resin 1338 c-Pr H NH2 CI H H Resin 133A c-Pr H OMe F H H Resin 1340 c-Pr H N02 F H H Resin 1341 c-Pr H NH2 F H H Resin 1342 c-Pr OMe H F H H Resin 1343 c-Pr F H F H H Resin 1344 c-Pr F H H H F Resin '~ X345 c-Pr H Me F H H Resin 1346 c-Pr H F F H H Resin 1347 c-Pr H F H F H Resin 1348 Me H F CH2OCH3 H H

1349 Me H CI CH20CH3 H H

1360 Me H Br CH20CH3 H H

X361 Me H CH3 CH2SCH3 H H

1352 Me H F CHZSCH3 H H

1353 Me H CI CH2SCH3 H H

1364 Me H Br CH2SCH3 H H

No. R3 R4 RS R6 R7 Re phys.
data 1x56Me H CH3 CH2NMe2 H H

1366Me H F CH2NMe2 H H

1367Me H CI CH2NMe2 H H

1368Me H Br CH2NMe2 H H

1368Me H CI CH3 H H

1360Me H Br CH3 H H

1364CZHS H Br CH20CH3 H H

1368C2H5 H Br CH2SCH3 H H

1369C2H5 H CH3 CH2NMe2 H H

137DC2H5 H F CHZNMe2 H H

'" 1371C2H5 H CI CH2NMez H H

1372C2H5 H Br CH2NMe2 H H

1373CzHs H CI CH3 H H

1374C2H5 H Br CH3 H H

Table 8: Compounds of the formula (8) F ~ Ra R5 N ~ N R3 R6 ($) No. R3 R4 R5 R6 R' R8 Phys.
data 1376 CH3 CH3 H F H H Resin 1380 CH3 i-Pr H CH2CgH5 H H

1383 CH3 Br H F H H

'~" 1384 CH3 I H i-Pr H H

1385 CH3 CH3 H OCHZPh H H

1386 CH3 CF3 H OPh H H

1387 CH3 OH H NOZ H H Resin 1388 CH3 OCH3 H NHZ H H Resin 1389 CH3 CH20Me H Ph H H

139o CH3 F H NHCOMe H H Resin 1391 CH3 CI H NHCHO H H Resin 1392 CH3 Br H N(S02Me)2 H H Resin 1393 CH3 I H NHSOZMe H H Resin ~

No. R3 R4 R5 R6 R' R8 Phys.
data 1394 CH3 CH3 H SMe H H

1395 CH3 CF3 H SOMe H H

1397 CH3 OCH3 H S02NHMe H H

1398 CH3 CH20Me H F H H

1401 CH3 Br H CH2N(CH3)2H H

140p CH3 I H CHZSCH3 H H

140(3CH3 CH3 H F H H

1406 CH3 CH2NMe2 H F H H

1406 CH3 CH2SMe H F H H

1414 CH3 CH20Me H H N(CH3)2 H Resin 1417 CH3 Br H H S02CH3 H

No. R3 R4 RS Rs R' Re Phys.
data ..

, . 1427 CH3 H N(CH3)2 F H H

1430 CH3 H N(S02CH3)2F H H

1432 CH3 H SMe F H H

1433 CH3 H SOMe F H H

'~' 1436 CH3 H S02N(CH3)2F H H

1440 CH3 H CHZN(CH3)2F H H

1444 CH3 H Br F H H

No. R3 R4 RS R6 R' Re Phys.
data 1446 CH3 H F c-Pr H H Resin 1447 CH3 H F CH2CsH5 H H Resin 1448 CH3 H F CH=CH2 H H Resin 1449 CH3 H F C---CH H H Resin 1450 CH3 H F H F H Oil 1451 CH3 F H CI F H Oil 1452 CHFMe H OMe Br H H Resin 1453 CHFMe H Me Br H H Resin 1454 CHFMe H N02 Br H H Resin 1456 CHFMe H NH2 Br H H Resin 1456 CHFMe H N02 C1 H H Resin 1457 CHFMe H NHZ CI H H Resin 1458 CHFMe H OMe F H H Resin 1499 CHFMe H N02 F H H Resin 1460 CHFMe H NH2 F H H Resin 1461 CHFMe OMe H F H H Resin 1462 CHFMe F H F H H Resin 1463 CHFMe F H H H F Resin 1464 CHFMe H F H F H Resin 1466 CHFMe H F F H H Resin 1466 CHFMe H Me F H H Resin 1467 CH3 H F CI H H Resin 1468 CH3 H CH3 H N02 H Resin 1469 CH3 H CF3 H NH2 H Resin X470 CH3 H OH H N(CH3)2 H Resin 1471 CH3 H OCH3 H NHCOCH3 H Resin No. R3 R4 R5 R6 R' RB Phys.
data t472 CH3 H N02 H NHCHO H Resin 1473 CH3 H NH2 H N(SOZCH3)2 H Resin t474 CH3 H NMe2 H NHS02CH3 H Resin 1477 CH3 H N(S02Me)2 H Br H

t478 CH3 H NHS02Me H I H

t479 CH3 H SCH3 H CH3 H

t480 CH3 H SOCH3 H CF3 H

t482 CH3 H S02NHMe H OCH3 H

1483 CH3 H S02NMe2 H SCH3 H

t484 CH3 H S02CH3 H SOCH3 H

t48,5 CH3 H CH20CH3 H S02NH2 H

t486 CH3 H F H S02NHCH3 H

1487 CH3 H CI H S02N(CH3)2 H

""~ 1488 CH3 H Br H SOZCH3 H

t489 CH3 H I H CzHS H

t491 CH3 CH3 F H CI H

t493 CH3 OCH3 CH3 H H F

t494 CH3 CI H F H CI

t495 CH3 H F F F H

t496 CH3 CI H F OCH3 H

No. R3 R4 RS Rs R' R8 Phys.
data 1506 CH3 H CI H CH=CHC2H5 H

1507 CH3 H CI H C =CC2H5 H

1508 CH3 H CI H CsHs H

1510 CH3 H CI -(CH2)a-1511 CH3 H CI -O(CH2)20-1513 C2H5 CH3 H CH3 H H Resin '""' 1514 C2H5 F H CH3 H H Resin 1515 C2H5 CH3 H CI H H Resin 1516 C2H5 H N(CH3)2 CI H H Resin 1517 C2H5 H S02CH3 CH3 H H Resin 1518 Me H Me Br H H

1519 Me H Me I H H

152D Et H Me F H H Resin 15e1 Et H Me CI H H

1522 Et H Me Br H H

l5zi Et H Me I H H

No. R3 R4 RS Rs R' Ra Phys.
data 1524 C~I-IS H F F H H Resin X525 C~I-15 H F H F H Resin 1526 c-Pr H OMe Br H H Resin 1527 c-Pr H Me Br H H Resin t528 c-Pr H N02 Br H H Resin t529 c-Pr H NH2 Br H H Resin 1530 c-Pr H N02 CI H H Resin .., 1531 c-Pr H NH2 CI H H Resin 1532 c-Pr H OMe F H H Resin 1533 c-Pr H NO2 F H H Resin 1534 c-Pr H NH2 F H H Resin 1536 c-Pr OMe H F H H Resin 1536 c-Pr F H F H H Resin 1537 c-Pr F H H H F Resin 1538 c-Pr H Me F H H Resin 1539 c-Pr H F F H H Resin 1540 c-Pr H F H F H Resin 1541 Me H Me CH20CH3 H H

1542 Me H F CH20CH3 H H

1543 Me H CI CH20CH3 H H

1544 Me H Br CH20CH3 H H

1545 Me H CH3 CH2SCH3 H H

1546 Me H F CH2SCH3 H H

1547 Me H CI CH2SCH3 H H

1548 Me H Br CH2SCH3 H H

1549 Me H CH3 CH2N(CH3)2H H

No. R3 R4 R5 R6 R' RB Phys.
data 1560 Me H F CH2N(CH3)2H H

1561 Me H CL CH2N(CH3)2H H

1562 Me H Br CH2N(CH3)2H H

1563 Me H CI CH3 H H

1564 Me H Br CH3 H H

1568 C2H5 H Br CH20CH3 H H

1562 CZHS H Br CH2SCH3 H H

1563 C2H5 H CH3 CH2N(CH3)2H H

1564 C2H5 H F CHZN(CH3)2H H

15~ C2H5 H CI CH2N(CH3)2H H

"""~ 1566 C2H5 H Br CH2N(CH3)2H H

1568 C2H5 H Br CH3 H H

Table 9 below refers to the formula (9) N ~ N R3 R6 (9) No. R' R2R3 R R5 R6 R' R8 Phys.
data 1571 CF3 H CH3 CI H F OCH3 H Oil 1575 c-Bu H CH3 H NMe2 CI H H

1576 c-Bu H CH3 H NMe2 S-Me H H

1577 c-Bu H CH3 H CH3 F H H

1578 c-Bu H H H CI H CI H Resin """"" 1579 c-Pen H CH3 H NMe2 CI H H

1580 c-Pen H CH3 H NMe2 S-Me H H Resin 1581 c-Pen H CH3 H CH3 F H H

1582 c-Hex H CH3 H NMe2 CI H H

1583 c-Hex H CH3 H NMe2 S-Me H H Resin 1584 c-Hex H CH3 H CH3 F H H

1585 CHMe- H CH3 H CH3 OCH3 H H Resin Ph(4-OH) 1586 t-Bu H CH3 H CH3 OCH3 H H Resin 1587 t-Bu H CH3 H OCH3 OCH3 H H Oil No. R' R2 R3 R4 R5 Rs R' R8 Phys.
data 1588 1-Me-c-PrH CH20-(3,5-H CI F H H 128 Me2-Ph) 1589 n-Pen H CH3 H OCH3 OCH3 H H Resin 1580 Bzl H CH3 H OCH3 OCH3 H H Resin ~ ~

Table 10 below refers to the formula (I) N N R
R6 (I) A N N
R2 R8 R~
No. A R' R2 R3 R4 R5 Re R' R8 Phys.
data 1591 NHZ CH3 CH3 CH3 H SMe H CH3 H

,,... 15A2 NHZ CH3 Ac CH3 H SMe H CH3 H

15ec3NHZ CH3 SOZMe CH3 H SMe H CH3 H

1594 NH2 CH3 c-Pr CH3 H SMe H CH3 H

1595 NHAc CH3 H CH3 H SMe H CH3 H Resin 15A6 NHAc CH3 H CH3 CF3 H SCH3 H H Resin 15A7 NHAc MeCHF H CH3 H OMe Br H H Resin 15A8 NHAc MeCHF H CH3 H Me Br H H Resin X599 NHAc MeCHF H CH3 H N02 Br H H Resin 1600 NHAc MeCHF H CH3 H NH2 Br H H Resin 1601 NHAc MeCHF H CH3 H N02 CI H H Resin No. A R' R2 R3 R4 RS R6 R' R8 Phys.
data 160e NHAc MeCHF H CH3 H NH2 CI H H Resin l6ociNHAc MeCHF H CH3 H OMe F H H Resin 1604 NHAc MeCHF H CH3 H N02 F H H Resin 1605 NHAc MeCHF H CH3 H NH2 F H H Resin 1606 NHAc MeCHF H CH3 OMe H F H H Resin 1607 NHAc MeCHF H CH3 F H F H H Resin 1608 NHAc MeCHF H CH3 F H H H F Resin "",, 1609 NHAc MeCHF H CH3 H CH3 F H H Resin 1610 NHAc MeCHF H CH3 H F F H H Resin 1611 NHAc MeCHF H CH3 H F H F H Resin 1612 NHAc EtCHF H CH3 H OMe Br H H Resin 1613 NHAc EtCHF H CH3 H Me Br H H Resin 1614 NHAc EtCHF H CH3 H N02 Br H H Resin 1615 NHAc EtCHF H CH3 H NH2 Br H H Resin 1616 NHAc EtCHF H CH3 H N02 CI H H Resin 1617 NHAc EtCHF H CH3 H NH2 CI H H Resin "'" 1618 NHAc EtCHF H CH3 H OMe F H H Resin 1619 NHAc EtCHF H CH3 H N02 F H H Resin lGdO NHAc EtCHF H CH3 H NH2 F H H Resin 1621 NHAc EtCHF H CH3 OMe H F H H Resin 1622 NHAc EtCHF H CH3 F H F H H Resin 162;1NHAc EtCHF H CH3 F H H H F Resin 1624 NHAc EtCHF H CH3 H CH3 F H H Resin 1625 NHAc EtCHF H CH3 H F F H H Resin 1626 NHAc EtCHF H CH3 H F H F H Resin 1627 H2NCONH MeCHF H CH3 H OMe Br H H Resin No. A R' R2 R3 R4 R5 R6 R' Rg Phys.
data 1628 H2NCONH MeCHF H CH3 H Me Br H H Resin 1629 H2NCONH MeCHF H CH3 H N02 Br H H Resin 1630 H2NCONH MeCHF H CH3 H NH2 Br H H Resin 1631 H2NCONH MeCHF H CH3 H N02 CI H H Resin 1632 H2NCONH MeCHF H CH3 H NHZ CI H H Resin 1633 H2NCONH MeCHF H CH3 H OMe F H H Resin 1634 H2NCONH MeCHF H CH3 H N02 F H H Resin 1635 H2NCONH MeCHF H CH3 H NH2 F H H Resin 1636 H2NCONH MeCHF H CH3 OMe H F H H Resin 1637 H2NCONH MeCHF H CH3 F H F H H Resin X638 H2NCONH MeCHF H CH3 F H H H F Resin 1639 H2NCONH MeCHF H CH3 H CH3 F H H Resin o H2NCONH MeCHF H CH3 H F F H H Resin 1641 H2NCONH MeCHF H CH3 H F H F H Resin 1642 H2NCONH EtCHF H CH3 H OMe Br H H Resin 1643 H2NCONH EtCHF H CH3 H Me Br H H Resin '~ 1644 H2NCONH EtCHF H CH3 H N02 Br H H Resin 1645 H2NCONH EtCHF H CH3 H NH2 Br H H Resin 1646 H2NCONH EtCHF H CH3 H N02 CI H H Resin X647 H2NCONH EtCHF H CH3 H NH2 CI H H Resin 1648 H2NCONH EtCHF H CH3 H OMe F H H Resin 1649 H2NCONH EtCHF H CH3 H N02 F H H Resin 1650 H2NCONH EtCHF H CH3 H NH2 F H H Resin H2NCONH EtCHF H CH3 OMe H F H H Resin 1652 H2NCONH EtCHF H CH3 F H F H H Resin 1663 H2NCONH EtCHF H CH3 F H H H F Resin No. A R' R2 R3 R4 RS R6 R' R8 Phys.
data 1664H2NCONH EtCHF H CH3 H CH3 F H H Resin 1665H2NCONH EtCHF H CH3 H F F H H Resin 1666H2NCONH EtCHF H CH3 H F H F H Resin 1667H2NCSNH MeCHF H CH3 H OMe Br H H Resin 1668H2NCSNH MeCHF H CH3 H Me Br H H Resin 166AH2NCSNH MeCHF H CH3 H N02 Br H H Resin 1660H2NCSNH MeCHF H CH3 H NH2 Br H H Resin 1661H2NCSNH MeCHF H CH3 H N02 CI H H Resin 1662H2NCSNH MeCHF H CH3 H NH2 CI H H Resin X663H2NCSNH MeCHF H CH3 H OMe F H H Resin 1664H2NCSNH MeCHF H CH3 H N02 F H H Resin 16E~H2NCSNH MeCHF H CH3 H NH2 F H H Resin 1666H2NCSNH MeCHF H CH3 OMe H F H H Resin 1667HZNCSNH MeCHF H CH3 F H F H H Resin 1668H2NCSNH MeCHF H CH3 F H H H F Resin 1668H2NCSNH MeCHF H CH3 H CH3 F H H Resin 1670HZNCSNH MeCHF H CH3 H F F H H Resin 1671H2NCSNH MeCHF H CH3 H F H F H Resin 1672HZNCSNH EtCHF H CH3 H OMe Br H H Resin 1673H2NCSNH EtCHF H CH3 H Me Br H H Resin 1674H2NCSNH EtCHF H CH3 H N02 Br H H Resin 1675H2NCSNH EtCHF H CH3 H NH2 Br H H Resin 16716H2NCSNH EtCHF H CH3 H N02 CI H H Resin 1677HZNCSNH EtCHF H CH3 H NH2 CI H H Resin X678HZNCSNH EtCHF H CH3 H OMe F H H Resin 16T9H2NCSNH EtCHF H CH3 H N02 F H H Resin No. A R' R2 R3 R4 RS Rs R' R8 Phys.
data X680 H2NCSNH EtCHF H CH3 H NH2 F H H Resin 1681 H2NCSNH EtCHF H CH3 OMe H F H H Resin 1682 H2NCSNH EtCHF H CH3 F H F H H Resin X683 HZNCSNH EtCHF H CH3 F H H H F Resin 1684 H2NCSNH EtCHF H CH3 H CH3 F H H Resin 1685 H2NCSNH EtCHF H CH3 H F F H H Resin 1686 H2NCSNH EtCHF H CH3 H F H F H Resin 1687 NH-S02Me CH3 H CH3 H SMe H CH3 H Resin X688 NH-S02Me CH3 H CH3 CF3 H SMe H H Resin 166A N=C(Me)OMeCH3 H CH3 CF3 H SMe H H Resin 1680 N=C(Me)OEtCH3 H CH3 CF3 H SMe H H Resin 1691 N=C(Me)SMeCH3 H CH3 CF3 H SMe H H Resin 1~2 N=CMe2 CH3 H CH3 CF3 H SMe H H Resin 1693 NH2 C2H5 CH3 CH3 H SMe H CH3 H

1694 NH2 C2H5 Ac CH3 H SMe H CH3 H

NH2 C2H5 S02Me CH3 H SMe H CH3 H

'~ t666 NHZ C2H5 c-Pr CH3 H SMe H CH3 H Resin 1697 NHCOCH3 C2H5 H CH3 H SMe H CH3 H

X699 NHS02CH3 C2H5 H CH3 H SMe H CH3 H Resin 1700 NHS02CH3 C2H5 H CH3 CF3 H SMe H H

1701 N=C(Me)OMeC2H5 H CH3 CF3 H SMe H H Resin 170e N=C(Me)OEtC2H5 H CH3 CF3 H SMe H H Resin 1700 N=C(Me)SMeC2H5 H CH3 CF3 H SMe H H Resin X704 N=C(CH3)2 C2H5 H CH3 CF3 H SMe H H Resin ' 1706 NH2 i-Pr CH3 CH3 H SMe H CH3 H

No. A R' R2 R3 R" RS Rs R' Re Phys.
data 1706 NH2 i-Pr Ac CH3 H SMe H CH3 H

1707 NHZ i-Pr SOZMe CH3 H SMe H CH3 H

1708 NHz i-Pr c-Pr CH3 H SMe H CH3 H Resin 17i0ANHCOCH3 i-Pr H CH3 H SMe H CH3 H Resin 1710 NHCOCH3 i-Pr H CH3 CF3 H SMe H H Resin 1711 NHS02CH3 i-Pr H CH3 H SMe H CH3 H Resin 1712 NHSOZCH3 i-Pr H CH3 CF3 H SCH3 H H Resin r~.
1713 N=C(Me)OMe i-Pr H CH3 CF3 H SCH3 H H Resin 1714 N=C(Me)OEt i-Pr H CH3 CF3 H SCH3 H H Resin 1715 N=C(Me)SMe i-Pr H CH3 CF3 H SCH3 H H Resin 1716 N=C(CH3)2 i-Pr H CH3 CF3 H SCH3 H H Resin 1717 NHZ CHFMe CH3 CH3 H SMe H CH3 H

1718 NH2 CHFMe Ac CH3 H SMe H CH3 H

1719 NH2 CHFMe S02Me CH3 H SMe H CH3 H

1720 NH2 CHFMe c-Pr CH3 H SMe H CH3 H Resin 1721 NHCOCH3 CHFMe H CH3 H SMe H CH3 H

""""' 1722 NHCOCH3 CHFMe H CH3 CF3 H SMe H H

1723 NHS02CH3 CHFMe H CH3 H SMe H CH3 H

1724 NHS02CH3 CHFMe H CH3 CF3 H SMe H H

1725 N=C(Me)OMe CHFMe H CH3 CF3 H SMe H H Resin 17x6 N=C(Me)OEt CHFMe H CH3 CF3 H SMe H H Resin 1727 N=C(Me)SMe CHFMe H CH3 CF3 H SMe H H Resin 1728 N=C(CH3)2 CHFMe H CH3 CF3 H SMe H H Resin 1729 NH2 CHFEt CH3 CH3 H SMe H CH3 H

t730 NH2 CHFEt Ac CH3 H SMe H CH3 H

1731 NH2 CHFEt S02Me CH3 H SMe H CH3 H

No. A R' R2 R3 R RS R6 R' Re Phys.
data 1732 NH2 CHFEt c-Pr CH3 H SMe H CH3 H Resin 1733 NHCOCH3 CHFEt H CH3 H SMe H CH3 H

1734 NHCOCH3 CHFEt H CH3 CF3 H SCH3 H H

1736 NHS02CH3 CHFEt H CH3 H SCH~H CH3 H

1736 NHS02CH3 CHFEt H CH3 CF3 H SCH3 H H

1737 N=C(Me)OMeCHFEt H CH3 CF3 H SCH3 H H Resin 1738 N=C(Me)OEtCHFEt H CH3 CF3 H SCH3 H H Resin 1739 N=C(Me)SMeCHFEt H CH3 CF3 H SCH3 H H Resin 1740 N=C(CH3)2 CHFEt H CH3 CF3 H SCH3 H H Resin 1741 NH2 CFMe2 CH3 CH3 H SMe H CH3 H

1742 NH2 CFMe2 Ac CH3 H SMe H CH3 H

1743 NH2 CFMe2 SOzMe CH3 H SMe H CH3 H

1744 NHZ CFMeZ c-Pr CH3 H SMe H CH3 H

1745 NHCOCH3 CFMe2 H CH3 H SMe H CH3 H

1746 NHCOCH3 CFMe2 H CH3 CF3 H SCH3 H H

1747 NHS02CH3 CFMe2 H CH3 H SCH~H CH3 H

1748 NHS02CH3 CFMe2 H CH3 CF3 H SCH3 H H

1749 N=C(Me)OMeCFMe2 H CH3 CF3 H SCH3 H H Resin 1750 N=C(Me)OEtCFMe2 H CH3 CF3 H SCH3 H H Resin 1751 N=C(Me)SMeCFMe2 H CH3 CF3 H SCH3 H H Resin 1752 N=C(CH3)2 CFMez H CH3 CF3 H SCH3 H H Resin 1753 NH2 c-Pr CH3 CH3 H SMe H CH3 H

1754 NH2 c-Pr Ac CH3 H SMe H CH3 H

1756 NH2 c-Pr S02Me CH3 H SMe H CH3 H

1756 NH2 c-Pr c-Pr CH3 H SMe H CH3 H Resin 1757 NHCOCH3 c-Pr H I CH3 H SMe H CH3 H Resin I I ( l I p I I I

No. A R' R2 R3 R4 RS Rs R' Re Phys.
data 1758NHCOCH3 c-Pr H CH3 CF3 H SCH3 H H Resin 1'759NHS02CH3 c-Pr H CH3 H SMe H CH3 H Resin NHS02CH3 c-Pr H CH3 CF3 H SCH3 H H Resin 1761N=C(Me)OMe c-Pr H CH3 CF3 H SCH3 H H Resin 1762N=C(Me)OEt c-Pr H CH3 CF3 H SCH3 H H Resin 1763N=C(Me)SMe c-Pr H CH3 CF3 H SCH3 H H Resin 1764N=C(CH3)2 c-Pr H CH3 CF3 H SCH3 H H Resin 1766NHZ 1-F-c-PrCH3 CH3 H SMe H CH3 H

1766NH2 1-F-c-PrAc CH3 H SMe H CH3 H

1767NH2 1-F-c-PrS02Me CH3 H SMe H CH3 H

1768NH2 1-F-c-Prc-Pr CH3 H SMe H CH3 H

1769NHCOCH3 1-F-c-PrH CH3 H SMe H CH3 H

1770NHCOCH3 1-F-c-PrH CH3 CF3 H SCH3 H H

1771NHS02CH3 1-F-c-PrH CH3 H SMe H CH3 H

1772NHS02CH3 1-F-c-PrH CH3 CF3 H SCHa H H

1773N=C(Me)OMe 1-F-c-PrH CH3 CF3 H SCH3 H H

1774N=C(Me)OEt 1-F-c-PrH CH3 CF3 H SCH3 H H

1775N=C(Me)SMe 1-F-c-PrH CH3 CF3 H SCH3 H H

1776N=C(CH3)2 1-F-c-PrH CH3 CF3 H SCH3 H H

1777CH3 CCI3 H CH3 H Br F H H Oil 1778CH3 CCI3 H CH3 H CH3 CI H H Oil 1779CH3 CGI3 H CH3 F H F H H Oil 1780Et CCI3 H CH3 H Br F H H

1781Et CCI3 H CH3 H CH3 CI H H

1782Et CCI3 H CH3 F H F H H

1783CH3 CFMe2 H CH3 H Br F H H

No. A R' RZ R3 R RS R6 R' R8 Phys.
data 1784 CH3 CFMe2 H CH3 H CH3 CI H H

1786 CH3 CFMe2 H CH3 F H F H H

1786 Et CFMe2 H CH3 H Br F H H

1787 Et CFMe2 H CH3 H CH3 CI H H

1788 Et CFMe2 H CH3 F H F H H

1789 CH3 c-Pr H CH3 H Br F H H

1730 CH3 c-Pr H CH3 H CH3 CI H H

1791 CH3 c-Pr H CH3 F H F H H

1792 i-Pr CCI3 H CH3 H Br F H H

1796 i-Pr CCI3 H CH3 H CH3 CI H H

1794 i-Pr CCI3 H CH3 F H F H H

1796 NHCOCH3 CCI3 H CH3 H Br F H H

1796 NHCOCH3 CCI3 H CH3 H Me CI H H

1798 NHS02Me CCI3 H CH3 H Br F H H

1799 NHS02Me CCI3 H CH3 H Me CI H H

'~ 1800 NHS02Me CCI3 H CH3 F H F H H

B. Formulation examples a) A dust is obtained by mixing 10 parts by weight of a compound of the formula (I) and 90 parts by weight of talc as inert substance and comminuting the mixture in a hammer mill.
b) A wettable powder which is readily dispersible in water is obtained by mixing 25 parts by weight of a compound of the formula (I), 64 parts by weight of kaolin-containing quartz as inert substance, 10 parts by weight of potassium lignosulfonate and 1 part by weight of sodium oleoylmethyltaurinate as wetter ""'' and dispersant and grinding the mixture in a pinned-disk mill.
c) A dispersion concentrate which is readily dispersible in water is obtained by mixing 20 parts by weight of a compound of the formula (I) 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, approx. 255 to above 277°C) and grinding the mixture in a ball mill to a fineness of below 5 microns.
d) An emulsifiable concentrate is obtained from 15 parts by weight of a compound of the formula (I), 75 parts by weight of cyclohexanone as solvent and 10 parts ,~. by weight of ethoxylated nonylphenol as emulsifier.
e) Water-dispersible granules are obtained by mixing 75 parts by weight of a compound of the formula (I), 10 " of calcium lignosulfonate, 5 " of sodium lauryl sulfate, 3 " of polyvinyl alcohol and 7 " of kaolin, grinding the mixture in a pinned-disk mill and granulating the powder in a fluidized bed by spraying on water as granulation liquid.
f) Water-dispersible granules are also obtained by homogenizing and precomminuting, on a colloid mill, 25 parts by weight of a compound of the formula (I), " of sodium 2,2'-dinaphthylmethane-6,6'-disulfonate, 2 " of sodium oleoylmethyltaurinate, 1 part by weight of polyvinyl alcohol, 5 17 parts by weight of calcium carbonate and 50 " of water, subsequently grinding the mixture in a bead mill and atomizing and drying the resulting suspension in a spray tower by means of a single-substance nozzle.
C. Biological examples 1. Pre-emergence effect on weeds Seeds or rhizome pieces of mono and dicotyledonous weed plants are placed in sandy lime soil in plastic pots and covered with soil. The compounds according to the invention which are formulated in the form of wettable powders or emulsion concentrates are then applied to the soil cover in the form of aqueous suspensions or emulsions at an application rate of 600 to 800 I of waterlha (converted), in various dosages.
After the treatment, the pots are placed in a greenhouse and kept under good growth ,,"" conditions for the weeds. After the test plants had emerged, the damage to the plants or the negative effect on the emergence was visually scored after a test period of 3 to 4 weeks by comparison with untreated controls. As shown by the test results, the compounds according to the invention have good herbicidal pre-emergence activity against a broad spectrum of weed grasses and broad-leaved weeds. For example, in the test the compounds of Example Nos. 4, 6, 12, 13, 15, 16, 17, 18, 46, 48, 49, 51, 67, 68, 69, 71-103, 124, 127, 131, 135-139, 145, 146, 158-174, 209, 215, 216, 218, 219, 220, 221, 242, 249, 251, 252, 254, 270, 272, 274-302, 334, 335, 336, 336, 344, 352, 356-371, 403, 407, 413, 414, 416-419, 440, 447, 449, 450, 452, 468, 470, 500, 524, 532, 542, 543, 544, 547, 551-567, 598, 600, 602-606, 609, 610, 612-615, 636, 643, 645, 646, 648, 664, 665, 666, 668-696, 714, 717, 718, 738, 742, 746-762, 793, 795, 830, 839, 840, 842, 859, 860, 862-890, 908, 911, 928, 936, 940-956, 987, 989, 991, 997, 998, 1000-1003, 1024, 1031, 1033, 1034, 1036, 1052-1054, 1056-1084, 1102, 1105, 1109, 1116, 1117, 1132, 1136-1152, 1182, 1193, 1194, 1196-1199, 1220, 1252-1280, 1319-1323, 1326, 1331-1347, 1388, 1389, 1390-1393,1414, 1446-1474, 1513-1517, 1520, 1524-1540, 1570, 1571, 1573, 1574, 1578, 1580, 1583, 1590, 1595-1692, 1696, 1699, 1701-1704, 1708-1715, 1720, 1725-1728, 1732, 1737-1740, 1749-1752, 1756-1764, 1777, 1778 and 1779 (see Tables 1 to 10) have very good herbicidal activity pre-emergence against harmful plants from the group consisting of Alopecurus spp., Apera spp., Poa spp., Echinochloa spp., Setaria spp., Digitaria spp., Chenopodium spp., Matricaria spp., Veronica spp., Viola spp., Stellaria spp., Amaranthus spp. or Solanum spp. at an application rate of 0.5 kg or less of active substance per hectare.
2. Post-emergence effect on weeds Seeds or rhizome pieces of mono- and dicotyledonous weeds are placed in sandy lime soil in plastic pots, covered with soil and grown in a greenhouse under good growth conditions. Three weeks after sowing, the test plants are treated at the three-leaf stage. The compounds according to the invention, formulated as wettable powders or emulsion concentrates, are sprayed, at various dosages, onto the green parts of the plants at an application rate of 600 to 8001 of water/ha (converted). After the test plants had remained in the greenhouse for about 3 to 4 weeks under optimum growth conditions, the effect of the preparations is scored visually by comparison with ,,~,, untreated controls. The agents according to the invention also have good herbicidal activity post-emergence against a broad spectrum of economically important weed grasses and broad-leaved weeds. For example, in the test the compounds of Example Nos. 4, 6, 12, 13, 15, 16, 17, 18, 46, 48, 49, 51, 67, 68, 69, 71-103, 124, 127, 131, 135-139, 145, 146, 158-174, 209, 215, 216, 218, 219, 220, 221, 242, 249, 251, 252, 254, 270, 272, 274-302, 334, 335, 336, 336, 344, 352, 356-371, 403, 407, 4013, 414, 416-419, 440, 447, 449, 450, 452, 468, 470, 472-500, 524, 532, 542, 543, 544, 547, 551-567, 598, 600, 602-606, 609, 610, 612-615, 636, 643, 645, 646, 648, 664, 665, 666, 668-696, 714, 717, 718, 738, 742, 746-762, 793, 795, 830, 839, 840, 842, 859, 860, 862-890, 908, 911, 928, 936, 940-956, 987, 989, 991, 997, 998, 1000-1003, 1024, 1031, 1033, 1034, 1036, 1052-1054, 1056-1084, 1102, 1105, 1109, 1116, 1117, 1132, 1136-1152, 1182, 1193, 1194, 1196-1199, 1220, 1252-1280, 1319-1323, 1326, 1331-1347, 1388, 1389, 1390-1393,1414, 1446-1474, 1513-1517, 1520, 1524-1540, 1570, 1571, 1573, 1574, 1578, 1580, 1583, 1585-1590, 1595-1692, 1696, 1699, 1704, 1708-1715, 1720, 1725-1728, 1732, 1737-1740, 1749-1752, 1756-1764, 1777, 1778 and 1779 (see Tables 1 to 10) have very good herbicidal activity post-emergence against harmful plants from the group consisting of Chenopodium spp., Papaver spp., Polygonum spp., Veronica spp. or Viola spp. at an application rate of 0.5 kg or less of active substance per hectare.
3. Action on harmful plants in rice Transplanted and sown rice and also typical rice weeds (gramineous and broad-,,.~, leafed) are cultivated in closed plastic pots in a greenhouse to the three-leaf stage (Echinochloa crus-galli 1.5-leaf) under paddy rice conditions (height of water: 2-3 cm).
This is followed by treatment with the novel compounds. For this purpose, the formulated active compounds are suspended, dissolved or emulsified in water and applied by pouring them into the dammed water around the test plants in different dosages.
After this treatment, the test plants are set up in the greenhouse under optimum growth conditions and are maintained in this way throughout the test period.
About three weeks after application, evaluation is made by visual scoring of the damage to the plants by comparison with untreated controls. The compounds according to the invention show very good herbicidal activity against harmful plants.
For example, the compounds of Example Nos. 4, 6, 12, 13, 15, 16, 17, 18, 46, 48, 49, 51, 67, 68, 69, 71-103, 124, 127, 131, 135-139, 145, 146, 158-174, 209, 215, 216, 218, 219, 220, 221, 242, 249, 251, 252, 254, 270, 272, 274-302, 334, 335, 336, 336, 344, 352, 356-371, 403, 407, 4013, 414, 416-419, 440, 447, 449, 450, 452, 468, 470, 472-500, 524, 532, 542, 543, 544, 547, 551-567, 598, 600, 602-606, 609, 610, 615, 636, 643, 645, 646, 648, 664, 665, 666, 668-696, 714, 717, 718, 738, 742, 762, 793, 795, 830, 839, 840, 842, 859, 860, 862-890, 908, 911, 928, 936, 940-956, 987, 989, 991, 997, 998, 1000-1003, 1024, 1031, 1033, 1034, 1036, 1052-1054, 1084, 1102, 1105, 1109, 1116, 1117, 1132, 1136-1152, 1182, 1193, 1194, 1196-1199, 1220, 1252-1280, 1319-1323, 1326, 1331-1347, 1388, 1389, 1390-1393,1414, 1446-1474, 1513-1517, 1520, 1524-1540, 1570, 1571, 1573, 1574, 1578, 1580, 1583, 1590, 1595-1692, 1696, 1699, 1701-1704, 1708-1715, 1720, 1725-1728, 1732, 1737-1740, 1749-1752, 1756-1764, 1777, 1778 and 1779 (see Tables 1 to 10) show very good herbicidal activity in the test against harmful plants which are typical for rice crops, for example Cyperus spp., Echinochloa spp., Digitaria spp., Sagitaria spp. and Scirpus spp.
4. Tolerance by crop plants In further greenhouse experiments, seeds of a substantial number of crop plants and weeds are placed in sandy lime soil and covered with soil. Some of the pots are treated immediately as described under Section 1, and the remaining pots are placed in the greenhouse until the plants have developed two to three true leaves and then sprayed with various dosages of the substances of the formula (I) according to the invention, as described under Section 2. Visual scoring four to five weeks after the application and after the plants have been in the greenhouse reveals that the compounds according to the invention left dicotyledonous crops such as soya, cotton, oilseed rape, sugar beet and potatoes unharmed even when high dosages of active ingredient were used by the pre- and post-emergence method. Moreover, some substances also spare Gramineae crops such as barley, wheat, rye, sorghum, com or rice. Some of the compounds of the formula (I) have high selectivity, and they are therefore suitable for controlling undesirable vegetation in agricultural crops.

Claims

Claims:

1. A compound of the formula (I) or a salt thereof in which A is a group of the formula NR a R b, in which R a and R b, independently of one another, are hydrogen, formyl or else aminocarbonyl, amino(thiocarbonyl), (C1-C10)alkyl, (C2-C10)alkenyl, (C2-C10)alkynyl, (C1-C10)alkylsulfinyl, (C1-C10)alkylsulfonyl, (C1-C10)alkoxy, [(C1-C10)alkyl]carbonyl, [(C1-C10)alkoxy]carbonyl, N-mono[(C1-C10)alkyl]aminocarbonyl, N,N-di[(C1-C10)alkyl]-aminocarbonyl, [(C1-C10)alkylthio]carbonyl, [(C1-C10)alkyl](thiocarbonyl), [(C1-C10)alkoxy](thiocarbonyl), N-mono[(C1-C10)alkyl]amino-(thiocarbonyl), N,N-di[(C1-C10)alkyl]amino(thiocarbonyl) or [(C1-C10)alkylthio](thiocarbonyl), where each of the 16 last-mentioned radicals is unsubstituted or substituted, or are (C3-C6)cycloalkyl, (C5-C6)cycloalkenyl, (C3-C6)cycloalkoxy, (C5-C6)cycloalkenyloxy, phenyl, phenoxy, phenylamino, phenylcarbonyl, naphthylcarbonyl, phenylsulfonyl, heterocyclyl, heterocyclyloxy, heterocyclylamino, heterocyclylcarbonyl or heterocyclylsulfonyl, where each of the 15 last-mentioned radicals is unsubstituted or substituted and heterocyclyl in the radicals mentioned is in each case heterocyclyl having 3 to 9 ring atoms, 1 to 4 of which are hetero ring atoms selected from the group consisting of N, O and S, or one of the radicals R a and R b is as defined above and the other of the radicals R a and R b is a group of the formula NR'R", where R' and R", independently of one another, are H or (C1-C6)alkyl which is unsubstituted or substituted, or R' and R" together are straight-chain (C2-C5)alkylene which is unsubstituted or substituted by one or more radicals selected from the group consisting of (C1-C4)alkyl, (C1-C4)alkoxy and (C1-C4)alkoxy-(C1-C4)alkyl, or R a and R b together are (C1-C10)alkylidene which is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, cyano, (C1-C4)alkoxy, (C1-C4)haloalkoxy and (C1-C4)alkylthio, or NR a R b together are a heterocyclyl radical which is attached to the nitrogen atom and has 3 to 6 ring atoms and, in addition to the nitrogen atom as hetero ring atom, optionally contains 1 to 3 further hetero ring atoms selected from the group consisting of N, O and S, where the heterocycle is unsubstituted or substituted, or A is (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C3-C6)cycloalkyl or (C5-C6)cycloalkenyl, where each of the 5 last-mentioned radicals is unsubstituted or substituted, and R1 is hydroxyl or (C1-C10)alkyl, which is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, hydroxyl, cyano, nitro, thiocyanato, formyl, amino, (C1-C4)alkoxy, (C1-C4)haloalkoxy, (C2-C4)alkenyloxy, (C2-C4)haloalkenyloxy, (C2-C4)alkynyloxy, (C2-C4)haloalkynyloxy, N-mono(C1-C4)alkylamino, N,N-di(C1-C4)alkylamino, (C1-C4)alkylthio, (C1-C4)alkylsulfinyl, (C1-C4)haloalkylsulfinyl, (C1-C4)alkylsulfonyl, (C1-C4)haloalkylsulfonyl, [(C1-C4)alkyl]carbonyl, [(C1-C4)haloalkyl]carbonyl, [(C1-C4)alkoxy]carbonyl, (C3-C9)cycloalkyl, (C5-C6)cycloalkenyl, phenyl and heterocyclyl, where each of the 4 last-mentioned radicals is unsubstituted or substituted, or is [(C1-C6)alkyl]carbonyl, [(C1-C6)alkoxy]carbonyl, (C1-C6)alkylsulfinyl or (C1-C4)alkylsulfonyl, where each of the 4 last-mentioned radicals is unsubstituted or substituted, or is (C3-C6)cycloalkyl, which is unsubstituted or substituted, (C5-C6)cycloalkenyl, which is unsubstituted or substituted, R2 is H or formyl, (C1-C10)alkyl, (C2-C10)alkenyl, (C2-C10)alkynyl, (C1-C10)alkylsulfinyl, (C1-C10)alkylsulfonyl, (C1-C10)alkoxy, [(C1-C10)alkyl]carbonyl, [(C1-C10)alkoxy]carbonyl, where each of the 8 last-mentioned radicals is unsubstituted or substituted, or is (C3-C6)cycloalkyl, (C5-C6)cycloalkenyl, (C3-C6)cycloalkoxy, (C5-C6)cycloalkenyloxy, phenyl, phenoxy, phenylamino, phenylcarbonyl, phenylsulfonyl, heterocyclyl, heterocyclyloxy, heterocyclylamino, heterocyclylcarbonyl or heterocyclylsulfonyl, where each of the 14 last-mentioned radicals is unsubstituted or substituted and heterocyclyl in the 5 last-mentioned radicals contains in each case 3 to 9 ring atoms, 1 to 4 of which are hetero ring atoms selected from the group consisting of N, O and S, or is a group of the formula NR c R d, where R c and R d, independently of one another, are H, formyl, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkylsulfinyl, (C1-C6)alkylsulfonyl, (C1-C6)alkoxy, [(C1-C6)alkyl]carbonyl or [(C1-C6)alkoxy]carbonyl, where each of the 8 last-mentioned groups is unsubstituted or substituted, or R c and R d together are straight-chain (C2-C5)alkylene, which is unsubstituted or substituted by one or more radicals selected from the group consisting of (C1-C4)alkyl, (C1-C4)alkoxy, (C1-C4)alkoxy-(C1-C4)alkyl and oxo, R3 is halogen, CN, NO2, SCN or a radical of the formula -X1-A1, where X1 is a direct bond or a divalent group of the formula -O-, -S(O)p-, -S(O)p-O-, -O-S(O)p-, -CO-, -O-CO-, -CO-O-, -S-CO-, -CO-S-, -S-CS-, -CS-S-, -O-CO-O-, -NR O -, -O-NR O-, -NR O-O-, -NR O-CO-, -CO-NR O-, -O-CO-NR O- or -NR O-CO-O-, in which in each case p is the integer 0, 1 or 2 and R O is hydrogen, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, phenyl, phenyl-(C1-C6)alkyl, (C3-C6)cycloalkyl or [(C1-C6)alkyl]carbonyl, and A1 is hydrogen, (C1-C10)alkyl, (C2-C10)alkenyl, (C2-C10)alkynyl, (C3-C6)cycloalkyl, (C5-C6)cycloalkenyl, phenyl or heterocyclyl having 3 to 9 ring atoms and 1 to 4 hetero ring atoms selected from the group consisting of N, O and S, where each of the 7 last-mentioned radicals is unsubstituted or substituted, each of the radicals R4, R5, R6, R7 and R8, independently of one another, is halogen, nitro, cyano, thiocyanato or a radical of the formula -X2-A2, where X2 is a direct bond or a divalent group of the formula -O-, -S(O)q-, -S(O)q-O-, -O-S(O)q-, -S(O)q-NR r-, -NR r-S(O)q-, -CO-, -O-CO-, -CO-O-, -S-CO-, -CO-S-, -S-CS-, -CS-S-, -O-CO-O-, -NR r -, -O-NR r-, -NR r-O-, -NR r-CO-, -CO-NR r-, -O-CO-NR r- or -NR r-CO-O-, in which in each case q is the integer 0, 1 or 2 and R r is hydrogen, amino, substituted amino, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, phenyl, phenyl-(C1-C6)alkyl, phenylcarbonyl, (C3-C6)cycloalkyl, (C5-C6)cycloalkenyl, [(C1-C6)alkyl]carbonyl, (C1-C6)alkylsulfonyl, (C1-C6)alkylsulfinyl, phenylsulfonyl or phenylsulfinyl, where each of the 13 last-mentioned radicals is unsubstituted or substituted, and A2 is hydrogen, (C1-C10)alkyl, (C2-C10)alkenyl, (C2-C10)alkynyl, (C3-C6)cycloalkyl, (C5-C6)cycloalkenyl, phenyl or heterocyclyl, where each of the 7 last-mentioned radicals is unsubstituted or substituted, or two adjacent radicals from the group consisting of R4, R5, R6, R7 and R8 together with the carbon atoms of the phenyl ring to which they are attached form a fused ring having 4 to 6 ring atoms which is carbocyclic or contains 1 to 3 hetero ring atoms from the group consisting of N, O and S and which is unsubstituted or substituted by one or more radicals selected from the group consisting of (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, [(C1-C6)alkyl]carbonyl, [(C1-C6)alkoxy]carbonyl, (C1-C6)alkylsulfonyl and (C1-C6)alkylsulfinyl, where at least two radicals selected from the group consisting of R4, R5, R6, and R8 are different from hydrogen, except for compounds of the formula (I) and salts thereof in which A is NH2, R1 is a radical of the formula -C(CH3)(X*)(R*), in which X* = halogen and R* =
H, CH3 or C2H5, R2 is H, R3 is CH3, R5 is CH3 or OCH3, R6 is CH3 or OCH3 and R4, R7 and R8 are each H.

2. A compound of the formula (I) or a salt thereof as claimed in claim 1, wherein A is a group of the formula NR a R b, in which R a and R b, independently of one another, are hydrogen, formyl, aminocarbonyl, amino(thiocarbonyl), (C1-C10)alkyl, (C2-C10)alkenyl, (C2-C10)alkynyl, (C1-C10)alkylsulfinyl, (C1-C10)alkylsulfonyl, (C1-C10)alkoxy, [(C1-C10)alkyl]carbonyl, [(C1-C10)alkoxy]carbonyl, N-mono[(C1-C10)alkyl]aminocarbonyl, N,N-di[(C1-C10)alkyl]aminocarbonyl, [(C1-C10)alkylthio]carbonyl, [(C1-C10)alkyl](thiocarbonyl), [(C1-C10)alkoxy](thiocarbonyl), N-mono[(C1-C10)alkyl]amino(thiocarbonyl), N,N-di[(C1-C10)alkyl]amino(thiocarbonyl) or [(C1-C10)alkylthio)(thiocarbonyl), where each of the 16 last-mentioned radicals is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C1-C4)alkoxy, (C1-C4)haloalkoxy, (C1-C4)hydroxyalkoxy and (C1-C4)alkoxy-(C1-C4)alkoxy, or are (C3-C6)cycloalkyl, (C5-C6)cycloalkenyl, (C3-C6)cycloalkoxy, (C5-C6)cycloalkenyloxy, phenyl, phenoxy, phenylamino, phenylcarbonyl, naphthylcarbonyl, phenylsulfonyl, heterocyclyl, heterocyclyloxy, heterocyclylamino, heterocyclylcarbonyl or heterocyclylsulfonyl, where each of the 15 last-mentioned radicals is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, cyano, hydroxyl, (C1-C4)alkyl, (C1-C4)haloalkyl, (C1-C4)hydroxyalkyl, (C1-C4)alkoxy-(C1-C4)alkyl, (C1-C4)alkoxy, (C1-C4)haloalkoxy, (C1-C4)hydroxyalkoxy and (C1-C4)alkoxy-(C1-C4)alkoxy, and heterocyclyl in the radicals mentioned is in each case heterocyclyl having 3 to 9 ring atoms, 1 to 4 of which are hetero ring atoms selected from the group consisting of N, O and S, or one of the radicals R a and R b is as defined above and the other of the radicals R a and R b is a group of the formula NR'R", where R' and R", independently of one another, are H or (C1-C6)alkyl, which is unsubstituted or substituted, preferably unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, hydroxyl, (C1-C4)alkoxy, (C1-C4)haloalkoxy, (C1-C4)hydroxyalkoxy and (C1-C4)alkoxy-(C1-C4)alkoxy, or R' and R" together are straight-chain (C2-C5)alkylene, which is unsubstituted or substituted by one or more radicals selected from the group consisting of (C1-C4)alkyl, (C1-C4)alkoxy and (C1-C4)alkoxy-(C1-C4)alkyl, or R a and R b together are (C1-C10)alkylidene, which is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, cyano, (C1-C4)alkoxy, (C1-C4)haloalkoxy and (C1-C4)alkylthio, or NR a R b together are a heterocyclyl radical which is attached to the nitrogen atom and has 3 to 6 ring atoms and, in addition to the nitrogen atom as hetero ring atom, optionally contains 1 to 3 further hetero ring atoms selected from the group consisting of N, O and S, where the heterocycle is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, cyano, hydroxyl, (C1-C4)alkyl, (C1-C4)haloalkyl, (C1-C4)hydroxyalkyl, (C1-C4)alkoxy, (C1-C4)haloalkoxy, (C1-C4)hydroxyalkoxy, (C1-C4)alkoxy-(C1-C4)alkoxy, (C1-C4)alkoxy-(C1-C4)alkyl and oxo, or A is (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C3-C6)cycloalkyl or (C5-C6)cycloalkenyl, where each of the 5 last-mentioned radicals is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C1-C4)alkoxy, (C1-C4)haloalkoxy, (C1-C4)alkylthio, (C1-C4)alkoxy-(C1-C4)alkoxy and, in the case of cyclic radicals, also (C1-C4)alkyl, (C1-C4)haloalkyl and (C1-C4)alkoxy-(C1-C4)alkyl, and R1 is hydroxyl or (C1-C10)alkyl, which is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, hydroxyl, cyano, nitro, thiocyanato, formyl, amino, (C1-C4)alkoxy, (C1-C4)haloalkoxy, (C2-C4)alkenyloxy, (C2-C4)haloalkenyloxy, (C2-C4)alkynyloxy, (C2-C4)haloalkynyloxy, N-mono(C1-C4)alkylamino, N,N-di(C1-C4)alkylamino, (C1-C4)alkylthio, (C1-C4)alkylsulfinyl, (C1-C4)haloalkylsulfinyl, (C1-C4)alkylsulfonyl, (C1-C4)haloalkylsulfonyl, [(C1-C4)alkyl]carbonyl, [(C1-C4)haloalkyl]carbonyl, [(C1-C4)alkoxy]carbonyl, (C3-C9)cycloalkyl, (C5-C6)cycloalkenyl, phenyl and heterocyclyl, where each of the 4 last-mentioned radicals is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, cyano, hydroxyl, (C1-C4)alkyl, (C1-C4)haloalkyl, (C2-C4)alkenyl, (C2-C4)haloalkenyl, (C2-C4)alkynyi, (C2-C4)haloalkynyl, (C1-C4)alkoxy, (C1-C4)haloalkoxy and (C1-C4)alkylthio, and heterocyclyl in each case contains 3 to 9 ring atoms, 1 to 4 of which are hetero ring atoms selected from the group consisting of N, O and S, or is [(C1-C6)alkyl]carbonyl, [(C1-C6)alkoxy]carbonyl, (C1-C6)alkylsulfinyl or (C1-C4)alkylsulfonyl, where each of the 4 last-mentioned radicals is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C1-C4)alkoxy, (C1-C4)haloalkoxy and (C1-C4)alkylthio, or is (C3-C6)cycloalkyl or (C5-C6)cycloalkenyl, where each of the two last-mentioned cyclic radicals is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, cyano, (C1-C4)alkyl, (C1-C4)haloalkyl, (C2-C4)alkenyl, (C2-C4)alkynyl, (C1-C4)alkoxy, (C1-C4)haloalkoxy and (C1-C4)alkylthio, where the radical R1, including substituents, has 1 to 30 carbon atoms, R2 is H or formyl, (C1-C10)alkyl, (C2-C10)alkenyl, (C2-C10)alkynyl, (C1-C10)alkylsulfinyl, (C1-C10)alkylsulfonyl, (C1-C10)alkoxy, [(C1-C10)alkyl]carbonyl, [(C1-C10)alkoxy]carbonyl, where each of the 8 last-mentioned radicals is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C1-C4,)alkoxy, (C1-C4)haloalkoxy, (C1-C4)hydroxyalkoxy and (C1-C4)alkoxy-(C1-C4)alkoxy, or is (C3-C6)cycloalkyl, (C5-C6)cycloalkenyl, (C3-C6)cycloalkoxy, (C5-C6)cycloalkenyloxy, phenyl, phenoxy, phenylamino, phenylcarbonyl, phenylsulfonyl, heterocyclyl, heterocyclyloxy, heterocyclylamino, heterocyclylcarbonyl or heterocyclylsulfonyl, where each of the 14 last-mentioned radicals is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, cyano, hydroxyl, (C1-C4)alkyl, (C1-C4)haloalkyl, (C1-C4)hydroxyalkyl, (C1-C4)alkoxy, (C1-C4)haloalkoxy, (C1-C4)hydroxyalkoxy, (C1-C4)alkoxy-(C1-C4)alkoxy, or is a group of the formula NR c R d, where R c and R d, independently of one another, are H, formyl, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkylsulfinyl, (C1-C6)alkylsulfonyl, (C1-C6)alkoxy, [(C1-C6)alkyl]carbonyl or [(C1-C6)alkoxy]carbonyl, where each of the 8 last-mentioned groups is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, hydroxyl, (C1-C4)alkoxy, (C1-C4)haloalkoxy, (C1-C4.)hydroxyalkoxy and (C1-C4)alkoxy-(C1-C4)alkoxy, or R c and R d together are straight-chain (C2-C5)alkylene, which is unsubstituted or substituted by one or more radicals selected from the group consisting of (C1-C4)alkyl, (C1-C4)alkoxy, (C1-C4)alkoxy-(C1-C4)alkyl and oxo, R3 is halogen, CN, NO2, SCN or a radical of the formula -X1-A1, where X1 is a direct bond or a divalent group of the formula -O-, -S(O)p-, -S(O)p-O-, -O-S(O)p-, -CO-, -O-CO-, -CO-O-, -S-CO-, -CO-S-, -S-CS-, -CS-S-, -O-CO-O-, -NR O-, -O-NR O-, -NR O-O-, -NR O-CO-, -CO-NR O-, -O-CO-NR O- or -NR O-CO-O-, in which in each case p is the integer 0, 1 or 2 and R O is hydrogen, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, phenyl, phenyl-(C1-C6)alkyl, (C3-C6)cycloalkyl or [(C1-C6)alkyl]carbonyl, and A1 is hydrogen, (C1-C10)alkyl, (C2-C10)alkenyl, (C2-C10)alkynyl, (C3-C6)cycloalkyl, (C5-C6)cycloalkenyl, phenyl or heterocyclyl having 3 to 9 ring atoms and 1 to 4 hetero ring atoms selected from the group consisting of N, O and S, where each of the 7 last-mentioned radicals is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, cyano, hydroxyl, (C1-C4)alkyl, (C3-C6)cycloalkyl, (C1-C4)alkoxy, (C1-C4)haloalkoxy and (C1-C4)hydroxyalkoxy and, in the case of cyclic radicals, also (C1-C4)haloalkyl, (C1-C4)alkoxy-(C1-C4)alkyl and (C1-C4)hydroxyalkyl and, including substituents, has up to 20 carbon atoms, each of the radicals R4, R5, R6, R7 and R8, independently of one another, is halogen, nitro, cyano, thiocyanato or a radical of the formula -X2-A2, where X2 is a direct bond or a divalent group of the formula -O-, -S(O)q-, -S(O)q-O-, -O-S(O)q-, -S(O)q-NR r-, -NR r-S(O)q-, -CO-, -O-CO-, -CO-O-, -S-CO-, -CO-S-, -S-CS-, -CS-S-, -O-CO-O-, -NR r -, -O-NR r-, -NR r-O-, -NR r-CO-, -CO-NR r-, -O-CO-NR r- or -NR r-CO-O-, in which in each case q is the integer 0, 1 or 2 and R r is hydrogen, amino, substituted amino, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, phenyl, phenyl-(C1-C6)alkyl, phenylcarbonyl, (C3-C6)cycloalkyl, (C5-C6)cycloalkenyl, [(C1-C6)alkyl]carbonyl, (C1-C6)alkylsulfonyl, (C1-C6)alkylsulfinyl, phenylsulfonyl or phenylsulfinyl, where each of the 13 last-mentioned radicals is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, cyano, hydroxyl, (C1-C4)alkyl, (C1-C4)alkoxy, (C1-C4)haloalkoxy and (C1-C4)hydroxyalkoxy and, in the case of cyclic radicals, also (C1-C4)haloalkyl, (C1-C4)alkoxy-(C1-C4)alkyl and (C1-C4)hydroxyalkyl, and A2 is hydrogen, (C1-C10)alkyl, (C2-C10)alkenyl, (C2-C10)alkynyl, (C3-C6)cycloalkyl, (C5-C6)cycloalkenyl, phenyl or heterocyclyl, where each of the 7 last-mentioned radicals is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, cyano, hydroxyl, amino, mercapto, aminocarbonyl, mono- and di(C1-C6)alkylamino, mono- and diarylamino, N-(C1-C6)alkyl-N-aryiamino, mono- and diacylamino, N-(C1-C6)alkyl-N-acylamino, N-arylN-acylamino, (C1-C6)alkoxy, (C1-C6)alkylthio, (C1-C6)alkylsulfonyl, (C1-C6)alkylsulfinyl, [(C1-C5)alkyl]carbonyl, [(C1-C5)alkoxy]carbonyl, [(C3-C6)alkyl]carbonyloxy, (C3-C6)cycloalkyl, (C3-C6)cycloalkoxy, (C3-C6)cycloalkylcarbonyl, (C3-C6)cycloalkylcarbonyloxy, phenyl, phenoxy, phenylthio, phenylcarbonyl, phenylcarbonyloxy, heterocyclyl, heterocyclyloxy, heterocyclylthio, heterocycfylcarbonyl, heterocyclylcarbonyloxy and, in the case of cyclic radicals, also (C1-C6)alkyl, where each of the 31 last-mentioned radicals is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, cyano, hydroxyl, amino, mono- and di(C1-C6)alkylamino, mono- and diarylamino, N-(C1-C6)alkyl-N-arylamino, mono- and di(C1-C6)acylamino, N-(C1-C6)alkyl-N-acyl-amino, (C1-C6)alkoxy, (C1-C6)alkylthio, (C3-C6)cycloalkyl, (C3-C6)cycloalkoxy, phenyl, phenoxy and phenylthio and, in the case of cyclic radicals, also by (C1-C6)alkyl, (C1-C6)haloalkyl and (C1-C4)alkoxy-(C1-C6)alkyl and where heterocyclyl in A2 in each case contains 3 to 9 ring atoms and 1 to 4 hetero ring atoms selected from the group consisting of N, O and S, and A2, including substituents, has up to 20 carbon atoms, or two adjacent radicals from the group consisting of R4, R5, R6, R7 and R8 together with the carbon atoms of the phenyl ring to which they are attached form a fused ring having 4 to 6 ring atoms, which is carbocyclic or contains 1 to 3 hetero ring atoms selected from the group consisting of N, O and S, and which is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C1-C6)alkyl, (C1-C6)haloalkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkoxy, [(C1-C6)alkyl]carbonyl, [(C1-C6)alkoxy]carbonyl, (C1-C6)alkylsulfonyl and (C1-C6)alkylsulfinyl, where at least two radicals, preferably 2 or 3 radicals, in particular 2 radicals, from the group consisting of R4, R5, R6, R7 and R8 are different from hydrogen.

3. A compound of the formula (I) and salts thereof as claimed in claim 1 or 2, wherein A is a group of the formula NR a R b, in which R a and R b, independently of one another, are hydrogen, formyl, aminocarbonyl, amino(thiocarbonyl), (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkylsulfinyl, (C1-C6)alkylsulfonyl, (C1-C6)alkoxy, [(C1-C6)alkyl]carbonyl, [(C1-C6)alkoxy]carbonyl, N-mono[(C1-C6)alkyl]aminocarbonyl, N,N-di[(C1-C6)alkyl]aminocarbonyl, [(C1-Cg)alkylthio]carbonyl, [(C1-C6)alkyl](thiocarbonyl), [(C1-C6)alkoxy](thiocarbonyl), N-mono[(C1-C6)alkyl]amino(thiocarbonyl), N,N-di[(C1-C6)alkyl]amino(thiocarbonyl), [(C1-C6)alkylthio](thiocarbonyl), where each of the 16 last-mentioned radicals is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C1-C4)alkoxy, (C1-C4)haloalkoxy, (C1-C4)hydroxyalkoxy and (C1-C4)alkoxy-(C1-C4)alkoxy, or are (C3-C6)cycloalkyl, (C3-C6)cycloalkoxy, phenyl, phenoxy, phenylamino, phenylcarbonyl, naphthylcarbonyl, phenylsulfonyl, heterocyclyl, heterocyclyloxy, heterocyclylamino, heterocyclylcarbonyl, heterocyclylsulfonyl, where each of the 12 last-mentioned radicals is unsubstituted or substituted by one or more of the radicals selected from the group consisting of halogen, cyano, (C1-C4)alkyl, (C1-C4)haloalkyl, (C1-C4)alkoxy-(C1-C4)alkyl, (C1-C4)alkoxy, (C1-C4)haloalkoxy and (C1-C4)alkoxy-(C1-C4)alkoxy, and heterocyclyl in the radicals mentioned is in each case heterocyclyl having 3 to 9 ring atoms, 1 to 3 of which are hetero ring atoms selected from the group consisting of N, O and S, or one of the radicals R a and R b is as defined above and the other of the radicals R a and R b is a group of the formula NR'R", where R' and R", independently of one another, are H or (C1-C4)alkyl, which is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C1-C4)alkoxy, (C1-C4)haloalkoxy and (C1-C4)alkoxy-(C1-C4)alkoxy, or R' and R" together are straight-chain (C2-C5)alkylene, which is unsubstituted or substituted by one or more radicals selected from the group consisting of (C1-C4)alkyl, (C1-C4)alkoxy and (C1-C4)alkoxy-(C1-C4)alkyl, or R a and R b together are (C1-C6)alkylidene, which is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, cyano, (C1-C4)alkoxy, (C1-C4)haloalkoxy and (C1-C4)alkylthio, or NR a R b together are a heterocyclyl radical which is attached to the nitrogen atom and has 3 to 6 ring atoms and, in addition to the nitrogen atom as hetero ring atom, optionally contains 1 to 3 further hetero ring atoms selected from the group consisting of N, O and S, where the heterocycle is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, cyano, (C1-C4)alkyl, (C1-C4)haloalkyl, (C1-C4)alkoxy, (C1-C4)haloalkoxy, (C1-C4)alkoxy-(C1-C4)alkoxy and (C1-C4)alkoxy-(C1-C4)alkyl, or A is (C1-C4)alkyl, (C2-C4)alkenyl, (C2-C4)alkynyl or (C3-C4)cycloalkyl, where each of the 4 last-mentioned radicals is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C1-C4)alkoxy, (C1-C4)haloalkoxy, (C1-C4)alkylthio, (C1-C4)alkoxy-(C1-C4)alkoxy and, in the case of cyclic radicals, also (C1-C4)alkyl, (C1-C4)haloalkyl and (C1-C4)alkoxy-(C1-C4)alkyl.

4. A compound of the formula (I) and salts thereof as claimed in any of claims 1 to 3, wherein R1 is (C1-C6)alkyl, which is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, hydroxyl, cyano, nitro, thiocyanato, formyl, amino, (C1-C4)alkoxy, (C1-C4)haloalkoxy, N-mono[(C1-C4)alkyl]amino, N,N-di((C1-C4)alkyl]amino, (C1-C4)alkylthio, (C1-C4)alkylsulfonyl, (C1-C4)haloalkylsulfonyl, [(C1-C4)alkyl]carbonyl, [(C1-C4)haloalkyl]carbonyl, [(C1-C4)alkoxy]carbonyl, (C3-C9)cycloalkyl, phenyl and heterocyclyl, where each of the 3 last-mentioned radicals is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, cyano, hydroxyl, (C1-C4)alkyl, (C1-C4)haioalkyl, (C1-C4)alkoxy, (C1-C4)haloalkoxy and (C1-C4)alkylthio and heterocyclyl contains in each case 3 to 9 ring atoms, 1 to 4 of which are hetero ring atoms selected from the group consisting of N, O and S, or is [(C1-C6)alkyl]carbonyl, [(C1-C6)alkoxy]carbonyl or (C1-C4)alkylsulfonyl, where each of the 3 last-mentioned radicals is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C1-C4)alkoxy, (C1-C4)haloalkoxy and (C1-C4)alkylthio, or is (C3-C6)cycloalkyl, which is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C1-C4)alkyl, (C1-C4)haloalkyl, (C1-C4)alkoxy, (C1-C4)haloalkoxy and (C1-C4)alkylthio.

5. A compound of the formula (I) and salts thereof as claimed in any of claims 1 to 4, wherein R2 is H or formyl, (C1-C4)alkyl, (C2-C4)alkenyl, (C2-C4)alkynyl, (C1-C4)alkylsulfinyl, (C1-C4)alkylsulfonyl, (C1-C4)alkoxy, [(C1-C4)alkyl]carbonyl or [(C1-C4)alkoxy]carbonyl, where each of the 8 last-mentioned radicals is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C1-C4)alkoxy and (C1-C4)haloalkoxy, or is (C3-C6)cycloalkyl, (C3-C6)cycloalkoxy, phenyl, phenoxy, phenylcarbonyl, phenylsulfonyl, heterocyclyl, heterocyclyloxy, heterocyclylcarbonyl or heterocyclylsulfonyl, where each of the 10 last-mentioned radicals is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, cyano, (C1-C4)alkyl, (C1-C4)haloalkyl, (C1-C4)alkoxy and (C1-C4)haloalkoxy and heterocyclyl in the radicals mentioned has in each case 3 to 9 ring atoms, 1 to 4 of which are hetero ring atoms selected from the group consisting of N, O and S, or is a group of the formula NR c R d, where R c and R d, independently of one another, are H, formyl, (C1-C4)alkyl, (C1-C4)alkylsulfonyl, (C1-C4)alkoxy, [(C1-C4)alkyl]carbonyl or [(C1-C4)alkoxy]carbonyl, where each of the 5 last-mentioned groups is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C1-C4)alkoxy, (C1-C4)haloalkoxy and (C1-C4)alkoxy-(C1-C4)alkoxy, or R c and R d together are straight-chain (C2-C5)alkylene which is unsubstituted or substituted by one or more radicals selected from the group consisting of (C1-C4)alkyl, (C1-C4)alkoxy, (C1-C4)alkoxy-(C1-C4)alkyl and oxo.

6. A compound of the formula (I) and salts thereof as claimed in any of claims 1 to 5, wherein R3 is halogen, CN, NO2, SCN or a radical of the formula -X1-A1, where X1 is a direct bond or a divalent group of the formula -O-, -S(O)p-, -S(O)p-O-, -O-S(O)p-, -CO-, -O-CO-, -CO-O-, -S-CO-, -CO-S-, -S-CS-, -CS-S-, -O-CO-O-, -NR O -, -O-NR O-, -NR O-O-, -NR O-CO-, -CO-NR O-, -O-CO-NR O- or -NR O-CO-O-, in which in each case p is the integer 0, 1 or 2 and R O is hydrogen, (C1-C4)alkyl, (C2-C4)alkenyl, (C2-C4)alkynyl, phenyl, phenyl-(C1-C2)alkyl, (C3-C6)cycloalkyl or [(C1-C4)alkyl]carbonyl, and A1 is hydrogen, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C3-C6)cycloalkyl, phenyl or heterocyclyl having 3 to 9 ring atoms and 1 to 3 hetero ring atoms selected from the group consisting of N, O and S, where each of the 6 last-mentioned radicals is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, cyano, (C1-C4)alkyl, (C3-C6)cycloalkyl, (C1-C4)alkoxy, (C1-C4)haloalkoxy, (C1-C4)alkylthio and, in the case of cyclic radicals, also (C1-C4)haloalkyl and (C1-C4)alkoxy-(C1-C4)alkyl and, including substituents, has up to 16 carbon atoms.

7. A compound of the formula (I) and salts thereof as claimed in any of claims 1 to 6, wherein each of the radicals R4, R5, R6, R7 and R8, independently of one another, is halogen, nitro, cyano, thiocyanato or a radical of the formula -X2-A2, where X2 is a direct bond or a divalent group of the formula -O-, -S(O)q-, -S(O)q-O-, -O-S(O)q-, -S(O)q -NR r-, -NR r-S(O)q-, -CO-, -O-CO-, -CO-O-, -S-CO-, -CO-S-, -S-CS-, -CS-S-, -O-CO-O-, -NR r-, -O-NR r-, -NR r-O-, -NR r-CO-, -CO-NR r-, -O-CO-NR r- or -NR r-CO-O-, preferably -O-, -S(O)q-, -S(O)q -O-, -S(O)q -NR r-, -NR r-S(O)q-, -CO-, -O-CO-, -CO-O-, -S-CO-, -CO-S-, -NR r-, -O-NR r-, -NR r-O-, -NR r-CO-, -CO-NR r-, -O-CO-NR r- or -NR r-CO-O-, in which in each case q is the integer 0, 1 or 2 and R r, in each case independently of one another, is hydrogen, amino, mono- or di(C1-C4)alkylamino, mono- or di(C1-C4)arylamino, N-(C1-C4)alkyl-N-aryl-amino, (C1-C4)alkyl, (C2-C4)alkenyl, (C2-C4)alkynyl, phenyl, phenyl-(C1-C4)alkyl, phenylcarbonyl, (C3-C6)cycloalkyl, (C5-C6)cycloalkenyl, [(C1-C4)alkyl]carbonyl, (C1-C4)alkylsulfonyl, (C1-C4)alkylsulfinyl, phenylsulfonyl or phenylsulfinyl, where each of the 18 last-mentioned radicals is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, cyano, (C1-C4)alkyl, (C1-C4)alkoxy, (C1-C4)haloalkoxy and, in the case of cyclic radicals, also (C1-C4)haloalkyl and (C1-C4)alkoxy-(C1-C4)alkyl, and A2 is hydrogen, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C3-C6)cycloalkyl, (C5-C6)cycloalkenyl, phenyl or heterocyclyl having 3 to 6 ring atoms and 1 to 3 hetero ring atoms selected from the group consisting of N, O and S, where each of the 7 last-mentioned radicals is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, cyano, hydroxyl, amino or else mercapto or aminocarbonyl, mono- and di(C1-C4)alkylamino, mono- and diphenylamino, N-(C1-C4)alkyl-N-phenylamino, mono- and di[(C1-C4)alkanoyl]amino, mono- and di[(C1-C4)alkylsulfonyl]amino, N-(C1-C4)alkyl-N-[(C1-C4)alkanoyl]amino, (C1-C4)alkyl-N-[(C1-C4)alkylsulfonyl]amino, N-phenyl-N-[(C1-C4)alkanoyl]amino, N-phenyl-N-[(C1-C4)alkylsulfonyl]amino, (C1-C4)alkoxy, (C1-C4)alkylthio, (C1-C4)alkylsulfonyl, (C1-C4)alkylsulfinyl, [(C1-C4)alkyl]carbonyl, [(C1-C4)alkoxy]carbonyl, [(C1-C4)alkyl]carbonyloxy, (C3-C6)cycloalkyl, (C3-C6)cycloalkoxy, (C3-C6)cycloalkylcarbonyl, (C3-C6)cycloalkylcarbonyloxy, phenyl, phenoxy, phenylthio, phenylcarbonyl, phenylcarbonyloxy, heterocyclyl, heterocyclyloxy, heterocyclylthio, heterocyclylcarbonyl, heterocyclylcarbonyloxy and, in the case of cyclic radicals, also (C1-C6)alkyl, where each of the 35 last-mentioned radicals is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, cyano, hydroxyl, amino, mono- and di-(C1-C4)alkylamino, mono- and diphenylamino, N-(C1-C4)alkyl-N-phenylamino, (C1-C4)alkoxy, (C1-C4)alkylthio, (C3-C6)cycloalkyl, (C3-C6)cycloalkoxy, phenyl, phenoxy and phenylthio and, in the case of cyclic radicals, also by (C1-C4)alkyl, (C1-C4)haloalkyl and (C1-C4)alkoxy-(C1-C4)alkyl, and A2, including substituents, has up to 16 carbon atoms, or two adjacent radicals from the group consisting of R4, R5, R6, R7 and R8 together with the carbon atoms of the phenyl ring to which they are attached form a fused ring having 4 to 6 ring atoms, which is carbocyclic or contains 1 to 3 hetero ring atoms selected from the group consisting of N, O and S and which is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C1-C4)alkyl, (C2-C4)alkenyl, (C2-C4)alkynyl, [(C1-C4)alkyl]-carbonyl, (C1-C6)alkoxy, [(C1-C4)alkoxy]carbonyl, (C1-C4)alkylsulfonyl and (C1-C4)alkylsulfinyl, where at least two radicals selected from the group consisting of R4, R5, R6, R7 and R8 are different from hydrogen.

8. A process for preparing the compound of the formula (I) or a salt thereof, as defined in any of claims 1 to 7, which comprises a) reacting a compound of the formula (II), R1 - Fu (II) in which Fu is a functional group selected from the group consisting of the carboxylic esters, carboxylic orthoesters, carbonyl chlorides, carboxamides, carboxylic anhydrides and trichloromethyl with a biguanidide of the formula (III) or an acid addition salt thereof or b) reacting a compound of the formula (IV), in which Z1 is an exchangeable radical or a leaving group with a suitable amine of the formula (V) or an acid addition salt thereof where in the formulae (II), (III), (IV) and (V) the radicals R1, R2, R3, R4, R5, R6, R7, R8 and A are as defined in formula (I).

9. A herbicidal or plant-growth-regulating agent which comprises one or more compounds of the formula (I) or salts thereof as claimed in any of claims 1 to 7 and formulation auxiliaries which are customary in crop protection.

10. A method for controlling harmful plants or for regulating the growth of plants, which comprises applying an effective amount of one or more compounds of the formula (I) or salts thereof as claimed in any of claims 1 to 7 to the plants, to plant seeds or to the area under cultivation.

11. The use of compounds of the formula (I) or salts thereof as claimed in any of claims 1 to 7 as herbicides or plant growth regulators.

12. The use as claimed in claim 11, wherein the compounds of the formula (I) or salts thereof are employed for controlling harmful plants or for regulating growth in crops of useful or ornamental plants.

13. The use as claimed in claim 12, wherein the crop plants are transgenic crop plants.