2-alkyl-or-aryl-substituted-2-(pyrimidinyl-or-traizinyl-oxy(or-thio))-acotic acid derivatives, process for preparation, and use as herbicides or plant-growth regulators

Abstract

Pyrimidinyl- or triazinyloxy- (or -thio)-carboxylic acid derivatives, processes for their preparation, and their use as herbicides or plant growth regulatorsCompounds of the formula (I) ##STR1## in which A is ##STR2## and R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6, X and Y are as defined in claim 1 are suitable as selective herbicides and plant growth regulators.

Description

It is known that pyrimidinyloxy(thio)- and triazinyloxy(thio)-carboxylic acid derivatives have herbicidal and plant-growth-regulating properties (see EP-A-0,347,811, EP-A-0,409,369 (CA-A-2,021,486), EP-A-0,409,368 (CA-A-2,021,486), EP-A-400,741). However, some of the known active substances of this structural type have disadvantages when used, for example insufficient selectivity in important crops.

Novel pyrimidinyloxy(thio)- and triazinyloxy(thio)-carboxylic acid derivatives which have advantageous herbicidal properties have now been found.

The invention relates to compounds of the formula (I) ##STR3## in which

A is a radical of the formula ##STR4##

X is O or S,

Y is N or CH,

R.sup.1 and R.sup.2 independently of one another are hydrogen, alkyl, alkoxy, alkylthio, halogen, haloalkoxy, amino, alkylamino or dialkylamino,

R.sup.3 is an aliphatic, araliphatic or aromatic radical of the formula ##STR5##

R.sup.5 is alkyl, alkenyl or alkynyl, the three last-mentioned radicals independently of one another being unsubstituted or mono- or polysubstituted by radicals selected from the group comprising alkoxy, alkylthio, amino, alkylamino, dialkylamino, nitro, halogen, phenyl and substituted phenyl, or

cycloalkyl or cycloalkenyl, the two last-mentioned radicals independently of one another being unsubstituted or mono- or polysubstituted by radicals selected from the group comprising alkyl, alkoxy, alkylthio, amino, alkylamino, dialkylamino, nitro, halogen, phenyl and substituted phenyl or a radical of the formula ##STR6##

R.sup.6 is hydrogen or alkyl,

R.sup.7 is hydrogen, halogen, alkyl which is unsubstituted or substituted by one or more radicals selected from the group comprising halogen, hydroxyl, alkoxy and alkylthio, or is cycloalkyl, hydroxyl, cyano, thienyl, naphthyl or dihydronaphthyl, the three last-mentioned radicals being unsubstituted or substituted, or is a radical of the formula ##STR7##

R.sup.13 is hydrogen, halogen, nitro, alkyl, haloalkyl, alkoxy, alkylsulfonyl, alkylsulfinyl or alkylthio,

R.sup.8 and R.sup.9 independently of one another are hydrogen or alkyl, or R.sup.8 and R.sup.9 together with the carbon atom linking them form a 3- to 6-membered ring which can contain an oxygen atom and be substituted by one or more alkyl groups,

R.sup.10 radicals independently of one another are hydrogen or alkyl, or R.sup.10 together with R.sup.12 and the ethylene group linking them are a cyclopentene or cyclohexene ring which is unsubstituted or substituted by one or more alkyl groups,

R.sup.11 is hydrogen or alkyl,

R.sup.12 is alkyl, phenyl or substituted phenyl, or R.sup.12 together with R.sup.10 and the ethylene group linking them are a cyclopentene or cyclohexene ring which is unsubstituted or substituted by one or more alkyl groups,

D.sup.1 to D.sup.6 independently of one another are O, S or NR.sup.14,

R.sup.14 is hydrogen, alkyl or phenyl,

n is an integer from 0 to 4, preferably 0 to 3,

m is an integer from 0 to 3, preferably 0 or 1,

o is an integer from 0 to 2, preferably 0 or 1,

P is an integer from 0 to 2, preferably 0 or 1,

Z independently of one another are halogen, alkyl, haloalkyl, alkoxy, haloalkoxy, alkylthio, amino, alkylamino, dialkyl amino, nitro, phenyl or substituted phenyl,

R.sup.4 is an alkoxy radical which is substituted by alkenyloxy, alkynyloxy, cycloalkyloxy, cyclo alkenyloxy, benzyloxy, benzylthio, (R*).sub.3 Si or (R*).sub.3 SiO, in which the radicals R* independently of one another are alkyl, alkenyl or alkynyl, aryl or substituted aryl, or by cyano, nitro, alkylcarbonyl, alkenylcarbonyl, alkynyl carbonyl, cycloalkylcarbonyl, alkylsulfonyl, alkylsulfinyl, dialkylphosphinyl, dialkyl phosphonyl, dialkylphosphoryl, pyridyl or substituted pyridyl, or

R.sup.4 is the radical of 5- or 6-membered cyclic lactone or R.sup.4 is a radical of the formula --D.sup.7 --CR.sup.15 R.sup.16 --D.sup.8 --L --NR.sup.32 --SO.sub.2 --R.sup.33 --NR.sup.34 --O--R.sup.35 --NR--N.dbd.CR.sup.21 R.sup.22 or ##STR8##

D.sup.7 is O, S or NR.sup.14,

D.sup.8 is a direct bond or a saturated or unsaturated hydrocarbon group, preferably a direct bond, CH.sub.2, CH(CH.sub.3) or C(CH.sub.3).sub.2,

R.sup.15 and R.sup.16 independently of one another are hydrogen, alkyl, alkenyl, alkynyl, aryl, substituted aryl, benzyl, alkoxy, alkenyloxy, alkynyloxy, aryloxy or substituted aryloxy,

L is an acid derivative radical of the formula

--CO--O--R.sup.17 --CO--S--R.sup.18 --CO--NR.sup.19 R.sup.20 --CO--O--N.dbd.CR.sup.21 R.sup.22 --CO--N.dbd.CR.sup.21 R.sup.22 --O--CO--R.sup.23 --S--CO--R.sup.23 --NR.sup.14 --CO--R.sup.23 ##STR9##

R.sup.17 and R.sup.18 are hydrogen, alkyl, alkenyl or alkynyl, the 3 last-mentioned radicals being unsubstituted or substituted by one or more radicals selected from the group comprising halogen, or are cycloalkyl, cycloalkenyl, benzyl, phenyl or substituted phenyl,

R.sup.19 and R.sup.20 independently of one another are hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, benzyl, phenyl or substituted phenyl, or together with the nitrogen atom linking them are a heterocyclic 3- to 7-membered ring which, besides the nitrogen atom, can additionally contain hetero atoms selected from the group comprising N, O and S,

R.sup.21 and R.sup.22 independently of one another are hydrogen, alkyl, alkenyl or alkynyl, or together with the carbon atom linking them are a carbocylic 4- to 8-membered radical,

R.sup.23 is hydrogen, alkyl, cycloalkyl, phenyl or substituted phenyl,

R.sup.24 is alkyl, alkenyl or alkynyl, the 3 last-mentioned radicals being unsubstituted or substituted by one or more radicals selected from the group comprising halogen, alkoxy, alkenyloxy and alkynyloxy, or are cycloalkyl, cycloalkenyl, alkanoyl, alkoxycarbonyl, benzyl, benzoxycarbonyl, phenyl or benzoyl, the 4 last-mentioned radicals being unsubstituted or substituted,

R.sup.25 is hydrogen, alkyl, alkanoyl, alkoxycarbonyl, alkenyloxycarbonyl, alkynyloxycarbonyl, phenyl or substituted phenyl,

R.sup.26 is hydrogen, alkyl, alkenyl or alkynyl, the 3 last-mentioned radicals being unsubstituted or substituted by one or more radicals selected from the group comprising halogen,

R.sup.27 and R.sup.28 independently of one another are hydrogen, alkyl, alkanoyl, alkoxycarbonyl, alkenyloxycarbonyl, alkynyloxycarbonyl, phenyl or substituted phenyl,

R.sup.29, R.sup.30 and R.sup.31 independently of one another are alkyl, alkenyl or alkynyl, phenyl or substituted phenyl,

R.sup.32 is hydrogen, alkyl, alkenyl, alkynyl, aryl or aralkyl,

R.sup.33 is alkyl, aryl, substituted aryl, aralkyl or substituted aralkyl,

R.sup.34 is hydrogen, alkyl, alkenyl, alkynyl, aryl or aralkyl and

R.sup.35 is hydrogen, alkyl, alkenyl, alkynyl, aryl or aralkyl.

In formula (I) and hereinafter, 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. Unless specifically indicated, preferred radicals are those where the carbon atom chains or carbon skeletons have 1 to 4 carbon atoms, or, in the case of unsaturated groups, 2 to 4 carbon atoms. Alkyl radicals, also in the composite meanings such as alkoxy, haloalkyl and the like, are methyl, ethyl, n- or i-propyl, n-, i-, t- or 2-butyl; alkenyl and alkynyl radicals have the meaning of the unsaturated radicals which are possible and which correspond to the alkyl radicals, such as 2-propenyl, 2- or 3-butenyl, 2-propynyl, and 2- or 3-butynyl. Halogen is fluorine, chlorine, bromine or iodine, haloalkyl is alkyl which is substituted by one or more atoms selected from the group comprising halogen; haloalkyl is, for example, CF.sub.3, CHF.sub.2, CH.sub.2 CF.sub.3. The same applies analogously to haloalkenyl, haloalkoxy and other halogen-substituted radicals. Aryl is, for example, phenyl, naphthyl, tetrahydronaphthyl, indenyl, indanyl, pentalenyl, fluorenyl and the like, preferably phenyl; aryloxy denotes the corresponding oxy radicals, preferably phenoxy. Heteroaryl, or heteroaryl in heteroaryloxy, denotes, for example, pyridyl, pyrimidyl, pyridazyl, thienyl, furyl, pyrrolyl, pyrazolyl and imidazolyl, preferably pyridyl and thienyl, but also bicyclic or polycyclic aromatic or araliphatic compounds. Optionally substituted aryl, aryloxy, heteroaryl, heteraryloxy, phenyl, phenoxy, benzyl and benzyloxy as well as bicyclic radicals having aromatic moieties preferably denote in each case the corresponding unsubstituted radical or denote a substituted radical derived therefrom, the substituents being, for example, one or more, preferably 1, 2 or 3, radicals selected from the group comprising halogen, alkyl, haloalkyl, alkoxy, haloalkoxy, nitro, cyano, alkoxycarbonyl, alkylcarbonyl, alkanoyl, carbamoyl, mono- and dialkylaminocarbonyl, mono- and dialkylamino, alkylsulfinyl and alkylsulfonyl and, in the case of radicals having carbon atoms, those having 1 to 4 carbon atoms, in particular 1 or 2, are preferred. Preferred substituents are, as a rule, those selected from the group comprising halogen, such as fluorine or chlorine, C.sub.1 -C.sub.4 -alkyl, preferably methyl or ethyl, C.sub.1 -C.sub.4 -haloalkyl, preferably trifluoromethyl, C.sub.1 -C.sub.4 -alkoxy, preferably methoxy or ethoxy, C.sub.1 -C.sub.1 -haloalkoxy, nitro and cyano. Methyl, methoxy and chlorine are particularly preferred.

Examples of silicon-containing radicals R.sup.4 are trialkylsilylalkoxy, aryldialkylsilylalkoxy, diarylalkylsilylalkoxy, trialkylsilylalkenyloxy, aryldialkylsilylalkenyloxy, diarylalkylsilylalkenyloxy, trialkylsilylalkynyloxy, aryldialkylsilylalkynyloxy, diarylalkylsilylalkynyloxy, trialkylsilyloxy, aryldialkylsilyloxy, diarylalkylsilyloxy.

The invention also relates to all stereoisomers and their mixtures which come under the formula (I) but are not specifically defined.

Particularly interesting compounds of the formula (I) according to the invention are those in which

R.sup.1, R.sup.2 independently of one another are C.sub.1 -C.sub.1 -alkyl, C.sub.1 -C.sub.1 -alkoxy, halogen, C.sub.1 -C.sub.1 -haloalkoxy, C.sub.1 -C.sub.1 -alkylamino or di-(C.sub.1 -C.sub.1 -alkyl)amino, preferably methyl, methoxy, chlorine or methylamino, in particular one of the two radicals being methoxy and the other radical being methyl, methoxy, chlorine or methylamino.

Other compounds of the formula (I) according to the invention which are of particular interest are those in which

A is a radical of the formula --CHR.sup.3 --CO--R.sup.4,

R.sup.3 is an aliphatic, araliphatic or aromatic radical of the formula --CR.sup.7 R.sup.8 R.sup.9 or phenyl, pyridyl or thienyl, where the 3 last-mentioned radicals are unsubstituted or substituted by 1 to 3 radicals Z,

R.sup.7 is hydrogen, halogen, C.sub.1 -C.sub.4 -alkyl, phenyl or benzyl, preferably hydrogen or methyl,

R.sup.8 and R.sup.9 independently of one another are hydrogen or C.sub.1 -C.sub.4 -alkyl, or R.sup.8 and R.sup.9 together with the carbon atom linking them are a 5- or 6-membered ring and

Z independently of one another are halogen, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkoxy, C.sub.1 -C.sub.4 alkylthio, C.sub.1 -C.sub.4 -alkylamino, di-(C.sub.1 -C.sub.4 -alkyl) amino or nitro.

R.sup.3 is preferably isopropyl, 2,2-dimethyl-ethyl or cyclopentyl.

Other compounds of the formula (I) according to the invention which are of particular interest are those in which

A is a radical of the formula ##STR10##

R.sup.5 is C.sub.1 -C.sub.4 -alkyl, C.sub.2 -C.sub.1 -alkenyl or C.sub.2 -C.sub.4 -alkynyl, cyclohexyl, cyclopentyl, phenyl, pyridyl or thienyl, where the 3 last-mentioned radicals are unsubstituted or substituted by 1 to 3 radicals Z,

R.sup.6 is hydrogen or C.sub.1 -C.sub.4 -alkyl and

Z independently of one another are halogen, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkoxy, C.sub.1 -C.sub.4 -alkylthio, C.sub.1 -C.sub.4 -alkylamino, di-(C.sub.1 -C.sub.4 -alkyl)amino or nitro.

Other compounds of the formula (I) according to the invention which are of particular interest are those in which

R.sup.4 is a C.sub.1 -C.sub.4 -alkoxy radical which is substituted by C.sub.2 -C.sub.1 -alkenyloxy, C.sub.2 -C.sub.4 -alkynyloxy, cyclohexyloxy, cyclohexenyloxy, cyclopentyloxy, cyclopentenyloxy, benzyloxy, benzylthio, (R*).sub.3 Si or (R*).sub.3 SiO, in which the radicals R* independently of one another are C.sub.1 -C.sub.4 -alkyl, C.sub.2 -C.sub.4 -alkenyl, C.sub.2 -C.sub.4 -alkynyl or phenyl, or by cyano, nitro, (C.sub.1 -C.sub.4 -alkyl)-carbonyl, C.sub.1 -C.sub.4 -alkylsulfonyl, C.sub.1 -C.sub.4 -alkylsulfinyl, di-(C.sub.1 -C.sub.4 -alkyl)-phosphinyl, di-(C.sub.1 -C.sub.1 -alkyl)-phosphonyl, di-(C.sub.1 -C.sub.1 -alkyl) -phosphoryl or pyridyl, or

R.sup.4 is the radical of a 5- or 6-membered cyclic lactone bonded to the remaining moiety in the .alpha.-position relative to the carbonyl group, or R.sup.4 is a radical of the formula ##STR11##

D.sup.7 is O, S, NH, methylamino or ethylamino,

D.sup.8 is a direct bond,

R.sup.15 and R.sup.16 independently of one another are hydrogen, C.sub.1 -C.sub.1 -alkyl, C.sub.2 -C.sub.4 -alkenyl, C.sub.2 -C.sub.4 -alkynyl, phenyl or benzyl, preferably hydrogen or methyl,

L is an acid derivative radical of the formula

--CO--O--R.sup.17 --CO--S--R.sup.18 --CO--NR.sup.19 R.sup.22 --CO--O--N.dbd.CR.sup.21 R.sup.22 --CO--N.dbd.CR.sup.21 R.sup.22 --O--CO--R.sup.23 --S--CO--R.sup.23 --NR.sup.14 --CO--R.sup.23 ##STR12##

R.sup.17 is hydrogen, C.sub.2 -C.sub.4 -alkenyl or C.sub.2 -C.sub.4 -alkynyl, cyclohexyl, cyclopentyl, cyclohexenyl, cyclopentenyl, benzyl, phenyl or substituted phenyl,

R.sup.18 is hydrogen, C.sub.1 -C.sub.4 -alkyl, C.sub.2 -C.sub.1 -alkenyl or C.sub.2 -C.sub.4 -alkynyl, cyclohexyl, cyclopentyl, cyclohexenyl, cyclopentenyl, benzyl, phenyl or substituted phenyl,

R.sup.19 and R.sup.20 independently of one another are hydrogen, C.sub.1 -C.sub.4 -alkyl, C.sub.2 -C.sub.4 -alkenyl, C.sub.2 -C.sub.4 -alkynyl, cyclohexyl, cyclopentyl, benzyl, phenyl or substituted phenyl, or, together with the nitrogen atom linking them, a heterocyclic 5- or 6-membered ring which, besides the nitrogen atom, can additionally contain an oxygen atom as hetero atom,

R.sup.21 and R.sup.22 independently of one another are C.sub.1 -C.sub.4 -alkyl, C.sub.2 -C.sub.1 -alkenyl or C.sub.2 -C.sub.4 -alkynyl or, together with the carbon atom linking them, a carbocylic 5- to 6-membered radical,

R.sup.23 is hydrogen, C.sub.1 -C.sub.4 -alkyl, cyclohexyl, cyclopentyl, phenyl or substituted phenyl,

R.sup.24 is C.sub.1 -C.sub.4 -alkyl, C.sub.2 -C.sub.4 -alkenyl or C.sub.2 -C.sub.4 -alkynyl, where the 3 last-mentioned radicals are unsubstituted or substituted by one or more radicals selected from the group comprising halogen or C.sub.1 -C.sub.4 -alkoxy, or is C.sub.1 -C.sub.4 -alkanoyl, (C.sub.1 -C.sub.4 -alkoxy) -carbonyl, benzyl, benzoxycarbonyl, phenyl or benzoyl, the 4 last-mentioned radicals being unsubstituted or substituted by C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, halogen or nitro,

R.sup.25 is hydrogen or C.sub.1 -C.sub.4 -alkyl,

R.sup.26 is hydrogen, C.sub.1 -C.sub.4 -alkyl, C.sub.2 -C.sub.4 -alkenyl or C.sub.2 -C.sub.4 -alkynyl, where the 3 last-mentioned radicals are unsubstituted or substituted by one or more radicals selected from the group comprising halogen,

R.sup.27, and R.sup.28 independently of one another are hydrogen or C.sub.1 -C.sub.4 -alkyl and

R.sup.29, R.sup.30 and R.sup.31 independently of one another are C.sub.1 -C.sub.4 -alkyl, C.sub.2 -C.sub.4 -alkenyl or C.sub.2 -C.sub.4 -alkynyl, phenyl or substituted phenyl.

Preferred compounds of the formula (I) according to the invention are those in which

R.sup.4 is a C.sub.1 -C.sub.4 -alkoxy radical which is substituted by allyl, propargyl, (R*).sub.3 Si or (R*).sub.3 SiO, in which the radicals R* independently of one another are methyl, ethyl or phenyl, or by cyano, C.sub.1 -C.sub.4 -alkylsulfonyl, C.sub.1 -C.sub.4 -alkylsulfinyl, di-(C.sub.1 -C.sub.4 -alkyl)-phosphinyl, di-(C.sub.1 -C.sub.4 -alkyl)-phosphonyl, di-(C.sub.1 -C.sub.4 -alkyl)-phosphoryl or pyridyl, or

R.sup.4 is the radical of a 5-membered cyclic lactone bonded to the remaining moiety in the .alpha.-position relative to the carbonyl group, or R.sup.4 is a radical of the formula --D.sup.7 --CR.sup.15 R.sup.16 --D.sup.8 --L or ##STR13##

D.sup.7 is O, S or NH,

D.sup.8 is a direct bond,

R.sup.15 and R.sup.16 independently of one another are hydrogen or methyl,

L is an acid derivative radical of the formula

--CO--O--R.sup.17 --CO--S--R.sup.18 --CO--N.dbd.CR.sup.21 R.sup.22 --CO--O--N.dbd.CR.sup.21 R.sup.22 ##STR14##

R.sup.17 is hydrogen, C.sub.2 -C.sub.4 -alkenyl or C.sub.2 -C.sub.4 -alkynyl, benzyl or phenyl,

R.sup.18 is hydrogen, C.sub.1 -C.sub.4 -alkyl, C.sub.2 -C.sub.4 -alkenyl or C.sub.2 -C.sub.4 -alkynyl, benzyl or phenyl,

R.sup.19 and R.sup.20 independently of one another are hydrogen, C.sub.1 -C.sub.4 -alkyl, C.sub.2 -C.sub.4 -alkenyl, C.sub.2 -C.sub.4 -alkynyl, cyclohexyl, cyclopentyl, benzyl, phenyl or substituted phenyl, or, together with the nitrogen atom linking them, a heterocyclic 5- or 6-membered ring which, besides the nitrogen atom, can additionally contain an oxygen atom as hetero atom,

R.sup.24 is C.sub.1 -C.sub.4 -alkyl where the last-mentioned radical is unsubstituted or substituted by one or more radicals selected from the group comprising halogen or C.sub.1 -C.sub.4 -alkoxy, or is C.sub.1 -C.sub.4 -alkanoyl, (C.sub.1 -C.sub.4 -alkoxy)-carbonyl, benzyl, benzoxycarbonyl, phenyl or benzoyl, where the 4 last-mentioned radicals are unsubstituted or substituted by C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, halogen or nitro,

R.sup.25 is hydrogen or C.sub.1 -C.sub.4 -alkyl,

R.sup.26 is hydrogen, C.sub.1 -C.sub.4 -alkyl, C.sub.2 -C.sub.4 -alkenyl or C.sub.2 -C.sub.4 -alkynyl,

R.sup.27 and R.sup.28 independently of one another are hydrogen or C.sub.1 -C.sub.4 -alkyl and

R.sup.29, R.sup.30 and R.sup.31 independently of one another are C.sub.1 -C.sub.4 -alkyl, C.sub.2 -C.sub.4 -alkenyl or C.sub.2 -C.sub.4 -alkynyl or phenyl.

Other preferred compounds of the formula (I) according to the invention are those in which the individual radicals and groups contain two or more of the radicals or groups mentioned above as being preferred.

The present invention furthermore relates to the process for the preparation of compounds of the formula I, which comprises

(a) if A is a radical of the formula --CHR.sup.3 --CO--R.sup.4, reacting a compound of the formula (II) ##STR15## in which R.sup.3, R.sup.4 and X are as defined in formula (I), with a compound of the formula (III) ##STR16## in which NUC.sup.1 is a leaving group, for example selected from the group comprising halogen, alkylsulfonyl, benzylsulfonyl and substituted benzylsulfonyl, and R.sup.1, R.sup.2 and Y are as defined in formula (I),

in the presence of an inorganic or organic base,

(b) if A is a radical of the formula --CHR.sup.3 --CO--R.sup.4, reacting a compound of the formula (IV) ##STR17## in which NUC.sup.2 is a leaving group, for example selected from the group comprising halogen and methylsulfonyloxy, and R.sup.3 and R.sup.4 are as defined in formula (I),

with a compound of the formula (V) ##STR18## in which R.sup.1, R.sup.2, X and Y are as defined in formula (I), in the presence of an inorganic or organic base,

(c) if A is the group ##STR19## reacting a compound of the formula (VI) ##STR20## in which

R.sup.1, R.sup.2, R.sup.4, X and Y are as defined in formula (I), with an aldehyde or ketone of the formula (VII)

R.sup.5 --CO--R.sup.6 (VII) in which R.sup.5 and R.sup.6 are as defined in formula (I), in the presence of a suitable inorganic or organic base, (d) if A is a radical of the formula --CHR.sup.3 --CO--R.sup.4, reacting a compound of the formula (VI) mentioned under (c) with a halogen compound of the formula (VIII) R.sup.3 --Hal (VIII) in which Hal is chlorine, bromine or iodine and R.sup.3 is as defined in formula (I), in the presence of an inorganic or organic base, or

(e) reacting a compound of the formula (IX) or (X) ##STR21## in which R.sup.1, R.sup.2, R.sup.3, R.sup.5, R.sup.6, X and Y are as defined in formula (I) and D* is O, S or NR.sup.14 where R.sup.14 is H, alkyl or phenyl, with a halogen compound of the formula (XI)

R.degree.--Hal (XI) in which R.degree. is defined such that R.degree.--D*-- has the meaning of R.sup.4 in formula (I), in the presence of an inorganic or organic base, or

(f) reacting a compound of the formula (IX) or (X) in which D* is an oxygen atom with thionyl chloride, oxalyl chloride, chlorocarbonate, carbonyldiimidazole or dicyclohexylcarbodiimide/4-N,N-dimethyl aminopyridine in a manner known per se to give an activated carboxylic acid derivative, and reacting the latter with a compound of the formula (XII)

R.sup.4 --H in the presence of an inorganic or organic base.

Bases which are suitable for the reactions (a) to (e) are, for example, inorganic bases from the group comprising the alkali metal carbonates, such as Na.sub.2 CO.sub.3, K.sub.2 CO.sub.3, NaHCO.sub.3 or KHCO.sub.3, alkali metal hydrides, such as NaH and KH, and alkali metal fluoride, such as KF, or organic bases such as triethylamine or DBU (1,8-diazabicyclo[5.4.0]undec-7-ene).

As a rule, it is expedient to carry out these reactions in the presence of a solvent, for example using a solvent such as toluene, xylene, diethylethane, diglyme, monoglyme, tetrahydrofuran, dioxane, dimethylformamide, N,N-dimethylacetamide, dimethyl sulfoxide or acetonitrile.

It can also be advantageous to carry out the reactions in the presence of catalysts, for example crown ethers or N,N,N',N', -tetramethylenediamine

Suitable bases for reaction (f) are, for example, alkali metals such as sodium or potassium, alkali metal carbonates, such as K.sub.2 CO.sub.3, Na.sub.2 CO.sub.3, NaHCO.sub.3 or KHCO.sub.3, alkali metal hydrides and alkaline earth metal hydrides such as NaH, KH or CaH.sub.2, alkali metal hydroxides such as KOH or NaOH, or organic bases such as triethylamine. Solvents which can be employed in this reaction are hydrocarbons such as n-heptane, benzene, toluene or xylene, halogenated hydrocarbons such as CH.sub.2 Cl.sub.2, CHCl.sub.3, CCl.sub.4 and chlorobenzene, alcohols such as CH.sub.3 OH, C.sub.2 H.sub.50 H or 2-propanol, ethers such as diethyl ether, dioxane and tetrahydrofuran (THF), ketones such as acetone or methyl ethyl ketone, esters such as ethyl acetate, aprotic polar solvents such as dimethylformamide (DMF), N,N-dimethylacetamide, dimethyl sulfoxide (DMSO), acetonitrile and water.

The starting materials of the formulae II-XII are known or can be synthesized analogously to known processes (cf. literature: EP-A-347,811, EP-A-409,369 (CA-A-2,021,486), EP-A-409,368 (CA-A-2,021,486), EP-A-400,741).

The compounds of the formula (I) according to the invention have an excellent herbicidal activity against a broad range of economical important monocotyledon and dicotyledon harmful plants. The active substances also act efficiently on perennial weeds which produce shoots from rhizomes, rootstocks or other perennial organs and which are difficult to control. In this context, it does not matter whether the substances are applied before sowing, pre-emergence or post-emergence.

Specifically, examples may be mentioned of some representatives of the monocotyledon and dicotyledon 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 substance acts 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, Imperata and Sorghum, and also perennial Cyperus species.

In the case of the dicotyledon weed species, the range of action extends to species such as, for example, Galium, Viola, Veronica, Lamium, Stellaria, Amaranthus, Sinapis, Ipomoea, Matricaria, Abutilon and Sida from amongst the annuals, and to Convolvulus, Cirsium, Rumex and Artemisia in the case of the perennial weeds.

The active substances according to the invention equally effect outstanding control of weeds 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 before 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, eventially, after three or four weeks have elapsed, they die completely.

If the active substances are applied post-emergence to the green parts of the plants, growth equally stops drastically a very short time after the treatment and the weed plants remain at the growth stage of the time of application, or they die completely after a certain time, so that in this manner competition by the weeds, which is harmful to the crop plants, is eliminated at a very early stage and in a sustained manner.

Although the compounds according to the invention have an excellent herbicidal activity against mono- and dicotyledon weeds, crop plants of economically important crops such as, for example, wheat, barley, rye, rice, maize, sugarbeet, 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 for agricultural purposes.

In addition, the substances according to the invention have excellent 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 undesired vegetative growth without simultaneously destroying the plants. Inhibition of the vegetative growth plays an important role in many monocotyledon and dicotyledon crops because lodging can be hereby reduced, or prevented completely.

The compounds according to the invention can be applied in the form of wettable powders, emulsifiable concentrates, sprayable solutions, dusts or granules, in the conventional preparations.

The compounds of the formula (I) can be formulated in various ways, depending on the prevailing biological and/or chemicophysical parameters. Examples of possible formulations which are suitable are: wettable powders (WP), emulsifiable concentrates (EC), concentrated emulsions (EW), for example oil-in-water or water-in-oil emulsions, sprayable solutions or emulsions, dispersions on an oil or water basis (SC), dusts (DP), seed-dressing agents, granules (G) such as granules for soil application and for broadcasting (FG), water-dispersible granules (WDG), ULV formulations, microcapsules or waxes.

These individual formulation types are known in principle and are described, for example, in: Winnacker-Kuchler, "Chemische Technologie" [Chemical Technology], Volume 7, C. Hauser Verlag Munich, 4th Ed. 1986; van Valkenburg, "Pesticides Formulations", Marcel Dekker N.Y., 2nd Ed. 1972-73; 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 also known and 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. Wiley and Sons, N.Y.; Marsden, "Solvents Guide", 2nd Ed., Interscience, N.Y. 1950; 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, "GrenzflaMchenaktive Athylenoxidaddukte" [Surface-Active Ethylene Oxide Adducts], Wiss. Verlagsgesell., Stuttgart 1976; Winnacker-Kuchler, "Chemische Technologie" [Chemical Technology], Volume 7, C. Hauser Verlag Munich, 4th Ed. 1986.

Wettable powders are preparations which are uniformly dispersible in water and which, besides the active substance and a diluent or inert substance, also contain wetting agents, for example polyoxyethylated alkylphenols, polyoxethylated fatty alcohols, alkane- or alkylarylsulfonates and fatty alcohol polyglycol ether sulfates, and dispersing agents, for example sodium ligninsulfonates, sodium 2,2'-dinaphthylmethane-6,6'-disulfonate, sodium dibutylnaphthalinesulfonate, or else sodium oleylmethyltaurinate.

Emulsifiable concentrates can be prepared by dissolving the active substance in an organic solvent, for example cyclohexanone, xylene or else higher-boiling aromatics or hydrocarbons, with the addition of one or more emulsifiers. Emulsifiers which can be used are, for example: calcium salts of alkylarylsulfonic acids, such as calcium dodecylbenzenesulfonate, fatty alcohol polyglycol ether sulfates or non-ionic emulsifiers such as fatty acid polyglycol esters, alkylaryl polyglycol ethers, fatty alcohol polyglycol ethers, propylene oxide/ethylene oxide condensation products (for example block polymers), fatty alcohol/propylene oxide/ethylene oxide condensation products, sorbitan fatty acid esters, polyoxyethylene sorbitan fatty acid esters or polyoxethylene sorbitol esters.

Dusts are obtained by grinding the active substance with finely divided solid substances, for example talc, natural clays, such as kaolin, bentonite and pyrophylite, or diatomaceous earths.

Granules such as granules for soil application or broadcasting, or water-dispersible granules, can be produced either by spraying the active substance onto adsorptive, granulated inert material or by applying active substance concentrates onto the surface of carriers such as sand, kaolinites or granulated inert material by means of binders, for example polyvinyl alcohol, sodium polyacrylate or alternatively mineral oils. Suitable active substances can also be granulated in the manner which is conventional for the production of fertilizer granules, if desired in a mixture with fertilizers.

Plate granules, fluidized-bed granules, extruded granules and spray granules can be produced by the customary processes; 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 et seq.; "Perry's Chemical Engineer's Handbook", 5th Ed., McGraw-Hill, New York 1973, p. 8-57.

For further information on the formulation of crop protection agents 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.

As a rule, the agrochemical preparations contain 0.1 to 99 percent by weight, in particular 0.1 to 95% by weight, of active substance of the formula (I).

In wettable powders, for example, the active substance concentration is approximately 10 to 90% by weight; the remainder to 100% is composed of customary formulation components. In the case of emulsifiable concentrates, the active substance concentration can be approximately 1 to 80, preferably 5 to 80, % by weight. Formulations in the form of dusts contain 1 to 30, preferably, in most cases, 5 to 20, % by weight of active substance, sprayable solutions approximately 0.2 to 25, preferably 2 to 20, % by weight of active substance. In the case of water-dispersible granules, the active substance content depends partly on whether the active compound is in solid or liquid form and on which granulation auxiliaries, fillers etc., are used.

In general, the content in the case of the water-dispersible granules is between 10 and 90% by weight.

In addition, the active substance formulations mentioned contain, if appropriate, the adhesives, wetting agents, dispersing agents, emulsifiers, penetrants, solvents, fillers or carriers which are conventional in each case.

Based on these formulations, it is also possible to prepare combinations with other pesticidally active substances, fertilizers and/or growth regulators, for example in the form of a readymix or a tank mix. Examples of active substances which can be used as components in the combinations with the active substances according to the invention are known active substances as are described, for example, in Weed Research 26, 441-445 (1986), or "The Pesticide Manual", 9th edition, The British Crop Protection Council, 1990/91, Bracknell, England, and in the literature cited therein. The following active substances may be mentioned, for example, as herbicides which are known from the literature and which can be combined with the compounds of the formula (I) (note: either the "common name" of the International Organization for Standardization (ISO) or the chemical name of the compounds is mentioned, if appropriate together with a customary code number): acetochlor; acifluorfen; aclonifen; AKH 7088, i.e. [[[1-[5-[2-chloro-4-(trifluoromethyl)-phenoxy]-2-nitrophenyl]-2-methoxyethylidene]-amino]-oxy]-acetic acid and methyl [[[1-[5-[2-chloro-4-(trifluoromethyl)-phenoxy]-2-nitrophenyl]-2-methoxyethylidene]-amino]-oxy]-acetate; alachlor; alloxydim; ametryn; amidosulfuron; amitrol; AMS, i.e. ammonium sulfamate; anilofos; asulam; atrazin; aziprotryn; barban; BAS 516 H, i.e. 5-fluoro-2-phenyl-4H-3,1-benzoxazin-4-one; benazolin; benfluralin; benfuresate; bensulfuron-methyl; bensulide; bentazone; benzofenap; benzofluor; benzoylprop-ethyl; benzthiazuron; bialaphos; bifenox; bromacil; bromobutide; bromofenoxim; bromoxynil; bromuron; buminafos; busoxinone; butachlor; butamifos; butenachlor; buthidazole; butralin; butylate; carbetamide; CDAA, i.e. 2-chloro-N,N-di-2-propenylacetamide; CDEC, i.e. 2-chloroallyl diethyldithiocarbamate; CGA 184927, i.e. 2-[4-[(5-chloro-3-fluoro-2-pyridinyl)oxy]phenoxy]propanoic acid and its 2-propynyl ester; chlomethoxyfen; chloramben; chlorazifop-butyl, pirifenopbutyl; chlorbromuron; chlorbufam; chlorfenac; chlorflurecol-methyl; chloridazon; chlorimuron ethyl; chlornitrofen; chlorotoluron; chloroxuron; chlorpropham; chlorsulfuron; chlorthal-dimethyl; chlorthiamid; cinmethylin; cinosulfuron; clethodim; clomazone; clomeprop; cloproxydim; clopyralid; cyanazine; cycloate; cycloxydim; cycluron; cyperquat; cyprazine; cyprazole; 2,4-DB; dalapon; desmediphan; desmetryne; di-allate; dicamba; dichlobenil; dichlorprop; diclofop-methyl; diethatyl; difenoxuron; difenzoquat; diflufenican; dimefuron; dimethachlor; dimethametryn; dimethazone, clomazon; dimethipin; dimetrasulfuron, cinosulfuron, dinitramine; dinoseb; dinoterb; dephenamid; dipropetryne; diquat; dithiopyr; diuron; DNOC; eglinazine-ethyl; EL 177, i.e. 5-cyano-1-(1,1-dimethylethyl)-N-methyl-3H-pyrazole-4-carboxamide; endothal; EPTC; esprocarb; ethalfluralin; ethametsulfuron-methyl; ethidimuron; ethiozine; ethofumesate; F5231, i.e. N-[2-chloro-4-fluoro-5-[4-(3-fluoropropyl)-4,5-dihydro-5-oxo-1H-tetrazol-1-yl]phenyl]ethanesulfonamide; F6285, i.e. 1-[5-(N-methylsulfonyl)amino-2,4-dichlorophenyl]-3-methyl-4-difluoromethyl-1,2,4-triazol-5-one; fenoprop; fenoxan, s. clomazon; fenoxaprop-ethyl; fenuron; flamprop-methyl; flazasulfuron; fluazifop and its ester derivatives; fluchloralin; flumetsulam; N-[2,6-difluorophenyl]-5-methyl-(1,2,4)-triazolo[1,5a]pyrimidine-2-sulfonamide; flumeturon; flumipropyn; fluorodifen; fluoroglycofen-ethyl; fluridone; flurochloridone; fluroxypyr; flurtamone; fomesafen; fosamine; furyloxyfen; glufosinate; glyphosate; halosafen; haloxyfop and its ester derivatives; hexazinone; Hw 52, i.e. N-(2,3-dichlorophenyl)-4-(ethoxymethoxy)benzamide; imazamethabenzmethyl; imazapyr; imazaquin; imazethamethapyr; imazethapyr; imazosulfuron; ioxynil, isocarbamide; isopropalin; isoproturon; isouron; isoxaben; isoxapyrifop; karbutilate; lactofen; lenacil; linuron; MCPA; MCPB; mecoprop; mefenacet; mefluidid, metamitrol; metazachlor; methabenzthiazuron; metham; methazole; methoxyphenone; methyldymron; metobromuron; metolachlor; 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; nittalin; nitrofen; nitrofluorfen; norflurazon; orbencarb; oryzalin; oxadiazon; oxyfluorfen; paraquat; pebulate; pendimethalin; perfluidone; phenmedipham; phenisopham; phenmedipham; picloram; piperophos; piributicarb; pirifenop-butyl; pretilachlor; primisulfuron-methyl; procyazine; prodiamine; profluralin; proglinazine-ethyl; prometon; prometryn; propachlor; propanil, propaquizafop and its ester derivatives; propazine; propham; propyzamide; prosulfalin; prosulfocarb; prynachlor; pyrazolinate; pyrazon; pyrazosulfuron-ethyl; pyrazoxyfen; pyridate; quinchlorac; quinmerac; quinofop and its ester derivatives, quizaolofop and its ester derivatives, quizalofop-ethyl; quizalofop-p-tefuryl; renriduron; dymron; S 275, i.e. 2-[4-chloro-2-fluoro-5-(2-propynyloxy)-phenyl]-4,5,6,7-tetrahydro-2H-indazole; S 482, i.e. 2-[7-fluoro-3,4-dihydro-3-oxo-4-(2-propynyl)-2H-1,4-benzoaxazin-6-yl]-4,5,6,7-tetrahydro-1H-isoindole-1,3(2H)-dione; secbumeton; sethoxydim; siduron; simazine; simetryn; SN 106279, i.e. 2-[[7-[2-chloro-4-(trifluoro-methyl)-phenoxy]-2-naphthalenyl]-oxy]propanoic acid and its methyl ester; sulfometuron-methyl; sulfazuron; flazasulfuron; TCA; tebutam; tebuthiuron; terbacil; terbucarb; terbuchlor; terbumeton; terbuthylazine; terbutryn; TFH 450, i.e. N,N-diethyl-3-[(2-ethyl-6-methylphenyl)-sulfonyl]-1H-1,2,4-triazole-1-carboxamide; thiazafluron; thifensulfuron-methyl; thiobencarb; tiocarbazil; tralkoxydim; tri-allate; triasulfuron; triazofenamide; tribenuron-methyl; triclopyr; tridiphane; trietazine; trifluralin; trimeturon; vernolate; WL 110547, i.e. 5-phenoxy-1-[3-(trifluoromethyl)-phenyl]-1H-tetrazole.

For use, the formulations present in commercially available form are diluted, if appropriate, in a conventional manner, for example using water in the case of wettable powders, emulsifiable concentrates, dispersions and water-dispersible granules. Preparations in the form of dust and granules for soil application or broadcasting and also sprayable solutions are usually not diluted with other inert substances before use.

The application rate of the compounds of the formula (I) required varies with the external conditions, such as temperature, humidity, and the nature of the herbicide used, amongst other factors. It can vary within wide limits, for example between 0,005 and 10.0 kg/ha or more of active ingredient, but it is preferably between 0.01 and 5 kg/ha.

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 ligninsulfonate and 1 part by weight of sodium oleoylmethyltaurinate as wetting and dispersion agent, and grinding the mixture on 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 (.RTM.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 approximately 255 to above 277.degree. 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 cyclohexane as solvent and 10 parts by weight of oxethylated nonylphenol as emulsifier.

e) Water-dispersible granules are obtained by mixing

______________________________________75 parts by weight of a compound of the formula (I),10 parts by weight of calcium ligninsulfonate, 5 parts by weight of sodium lauryl sulfate, 3 parts by weight of polyvinyl alcohol and 7 parts by weight 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

______________________________________25 parts by weight of a compound of the formula (I), 5 parts by weight of sodium 2,2'-dinaphthylmethane- 6,6'-disulfonate, 2 parts by weight of sodium oleoylmethyltaurinate, 1 part by weight of polyvinyl alcohol,17 parts by weight of calcium carbonate and50 parts by weight of water______________________________________ in a colloid mill, subsequently grinding the mixture in a bead mill and atomizing and drying the resulting suspension in a spray tower by means ofa single-substance nozzle.

CHEMICAL EXAMPLES

(Benzyloxycarbonyl)methyl 2-(4,6-dimethoxypyrimidinyl-2-oxy)-3-methylbutanoate (Ex. 61)

0.91 g (15.6 mmol) of potassium fluoride is added with stirring at room temperature to a solution of 4 g (15.6 mmol) of 2-(4,6-dimethoxypyrimidinyl-2-oxy)-3-methylbutanoic acid and 3.58 g (15.6 mmol) of benzyl bromoacetate in 25 ml of dimethylformamide. After stirringat 90.degree. C. for 10 hours, the reaction solution is poured into ice-water and the mixture is extracted with ethyl acetate. Evaporation on a rotary evaporator yields 5.19 g of the title compound (Ex. 61) in the form of a colorless oil.

(Trimethylsilyl)methyl 2-(4,6-dimethoxypyrimidinyl-2-oxy)-3-methylbutanoate(Ex. 391)

2.41 g (11.7 mmol) of dicyclohexylcarbodiimide are added dropwise with stirring at 20.degree. C. to a solution of 3 g (11.7 mmol) of 2-(4,6-dimethoxypyrimidinyl-2-oxy)-3-methylbutanoic acid, 1.22 g (11.7 mmol) of trimethylsilylmethanol and 0.05 g of 4-dimethylaminopyridine in 25 ml of CH.sub.2 Cl.sub.2. After stirring at room temperature for 12 hours followed by column filtration, 2.9 g of the title compound (Ex. 391)are obtained in the form of a colorless oil.

The remaining compounds of Table I below are obtained analogously to the above-described examples and process variants.

TABLE I__________________________________________________________________________Compounds of the formula Ia ##STR22## (Ia)" ##STR23## (Ia)Ex. m.p.(.degree.C.)No. R.sup.1 R.sup.2 X Y R.sup.3 R.sup.4 or [n].sub.D.sup.20__________________________________________________________________________1 OCH.sub.3 OCH.sub.3 O CH i-C.sub.3 H.sub.7 OCH.sub.2 COOCH.sub.2 CHCH.sub.2 522 Cl " " " " "3 CH.sub.3 " " " " "4 NHCH.sub.3 " " " " "5 OCH.sub.3 " S " " "6 Cl " " " " "7 CH.sub.3 " " " " "8 NHCH.sub.3 " " " " "9 OCH.sub.3 " " N " "10 " " O " " "11 " " " CH t-C.sub.4 H.sub.9 "12 Cl " " " " "13 CH.sub.3 " " " " "14 NHCH.sub.3 " " " " "15 OCH.sub.3 " " " " "16 Cl " " " " "17 CH.sub.3 " " " " "18 NHCH.sub.3 " " " " "19 OCH.sub.3 " " N " "20 " " O " " "21 " " " CH cyclopentyl " 56-5722 Cl " " " " "23 CH.sub.3 " " " " "24 NHCH.sub.3 " " " " "25 OCH.sub.3 " S " " "26 Cl " " " " "27 CH.sub.3 " " " " "28 NHCH.sub.3 " " " " "29 OCH.sub.3 " " N " "30 " " O " " "31 OCH.sub.3 OCH.sub.3 O CH i-C.sub.3 H.sub.7 OCH.sub.2 COOCH.sub.2 CCH 9832 Cl " " " " "33 CH.sub.3 " " " " "34 NHCH.sub.3 " " " " "35 OCH.sub.3 " S " " "36 Cl " " " " "37 CH.sub.3 " " " " "38 NHCH.sub.3 " " " " "39 OCH.sub.3 " " N " "40 " " O " " "41 " " " " t-C.sub.4 H.sub.9 "42 Cl " " " " "43 CH.sub.3 " " " " "44 NHCH.sub.3 " " " " "45 OCH.sub.3 " " " " "46 Cl " " " " "47 CH.sub.3 " " " " "48 NHCH.sub.3 " " " " "49 OCH.sub.3 " " N " "50 " " O " " "51 " " " CH cyclopentyl " 81-8252 Cl " " " " "53 CH.sub.3 " " " " "54 NHCH.sub.3 " " " " "55 OCH.sub.3 " S " " "56 Cl " " " " "57 CH.sub.3 " " " " "58 NHCH.sub.3 " " " " "59 OCH.sub.3 " " N " "60 " " O " " "61 OCH.sub.3 OCH.sub.3 O CH i-C.sub.3 H.sub.7 OCH.sub.2 COOCH.sub.2 Ph oil62 Cl " " " " "63 CH.sub.3 " " " " "64 NHCH.sub.3 " " " " "65 OCH.sub.3 " S " " "66 Cl " " " " "67 CH.sub.3 " " " " "68 NHCH.sub.3 " " " " "69 OCH.sub.3 " " N " "70 " " O " " "71 " " " " t-Bu "72 Cl " " " " "73 CH.sub.3 " " " " "74 NHCH.sub.3 " " " " "75 OCH.sub.3 " " " " "76 Cl " " " " "77 CH.sub.3 " " " " "78 NHCH.sub.3 " " " " "79 OCH.sub.3 " " N " "80 " " O " " "81 " " " CH cyclopentyl " 66-6882 Cl " " " " "83 CH.sub.3 " " " " "84 NHCH.sub.3 " " " " "85 OCH.sub.3 " S " " "86 Cl " " " " "87 CH.sub.3 " " " " "88 NHCH.sub.3 " " " " "89 OCH.sub.3 " " N " "90 " " O " " "91 OCH.sub.3 OCH.sub. 3 O CH i-C.sub.3 H.sub.7 OCH.sub.2 COSCH.sub.392 Cl " " " " "93 CH.sub.3 " " " " "94 NHCH.sub.3 " " " " "95 OCH.sub.3 " S " " "96 Cl " " " " "97 CH.sub.3 " " " " "98 NHCH.sub.3 " " " " "99 OCH.sub.3 " " N " "100 " " O " " "101 " " " " t-Bu "102 Cl " " " " "103 CH.sub.3 " " " " "104 NHCH.sub.3 " " " " "105 OCH.sub.3 " " " " "106 Cl " " " " "107 CH.sub.3 " " " " "108 NHCH.sub.3 " " " " "109 OCH.sub.3 " " N " "110 " " O " " "111 " " " CH cyclopentyl "112 Cl " " " " "113 CH.sub.3 " " " " "114 NHCH.sub.3 " " " " "115 OCH.sub.3 " S " " "116 Cl " " " " "117 CH.sub.3 " " " " "118 NHCH.sub.3 " " " " "119 OCH.sub.3 " " N " "120 " " O " " "121 OCH.sub.3 OCH.sub.3 O CH i-C.sub.3 H.sub.7 OCH.sub.2 COSC.sub.2 H.sub.5122 Cl " " " " "123 CH.sub.3 " " " " "124 NHCH.sub.3 " " " " "125 OCH.sub.3 " S " " "126 Cl " " " " "127 CH.sub.3 " " " " "128 NHCH.sub.3 " " " " "129 OCH.sub.3 " " N " "130 " " O " " "131 " " " " t-Bu "132 Cl " " " " "133 CH.sub.3 " " " " "134 NHCH.sub.3 " " " " "135 OCH.sub.3 " " " " "136 Cl " " " " "137 CH.sub.3 " " " " "138 NHCH.sub.3 " " " " "139 OCH.sub.3 " " N " "140 " " O " " "141 " " " CH cyclopentyl "142 Cl " " " " "143 CH.sub.3 " " " " "144 NHCH.sub.3 " " " " "145 OCH.sub.3 " S " " "146 Cl " " " " "147 CH.sub.3 " " " " "148 NHCH.sub.3 " " " " "149 OCH.sub.3 " " N " "150 " " O " " "151 OCH.sub.3 OCH.sub.3 O CH i-C.sub.3 H.sub.7 OCH.sub.2 COSCH.sub.2 Ph152 Cl " " " " "153 CH.sub.3 " " " " "154 NHCH.sub.3 " " " " "155 OCH.sub.3 " S " " "156 Cl " " " " "157 CH.sub.3 " " " " "158 NHCH.sub.3 " " " " "159 OCH.sub.3 " " N " "160 " " O " " "161 " " " " t-Bu "162 Cl " " " " "163 CH.sub.3 " " " " "164 NHCH.sub. 3 " " " " "165 OCH.sub.3 " " " " "166 Cl " " " " "167 CH.sub.3 " " " " "168 NHCH.sub.3 " " " " "169 OCH.sub.3 " " N " "170 " " O " " "171 " " " CH cyclopentyl "172 Cl " " " " "173 CH.sub.3 " " " " "174 NHCH.sub.3 " " " " "175 OCH.sub.3 " S " " "176 Cl " " " " "177 CH.sub.3 " " " " "178 NHCH.sub.3 " " " " "179 OCH.sub.3 " " N " "180 " " O " " "181 OCH.sub.3 OCH.sub.3 O CH i-C.sub.3 H.sub.7 OCH(CH.sub.3)COOCH.sub.2 CHCH.sub.2182 Cl " " " " "183 CH.sub.3 " " " " "184 NHCH.sub.3 " " " " "185 OCH.sub.3 " S " " "186 Cl " " " " "187 CH.sub.3 " " " " "188 NHCH.sub.3 " " " " "189 OCH.sub.3 " " N " "190 " " O " " "191 " " " " t-C.sub.4 H.sub.9 "192 Cl " " " " "193 CH.sub.3 " " " " "194 NHCH.sub.3 " " " " "195 OCH.sub.3 " " " " "196 Cl " " " " "197 CH.sub.3 " " " " "198 NHCH.sub.3 " " " " "199 OCH.sub.3 " " N " "200 " " O " " "201 " " " CH cyclopentyl " 62-64202 Cl " " " " "203 CH.sub.3 " " " " "204 NHCH.sub.3 " " " " "205 OCH.sub.3 " S " " "206 Cl " " " " "207 CH.sub.3 " " " " "208 NHCH.sub.3 " " " " "209 OCH.sub.3 " " N " "210 " " O " " "211 OCH.sub.3 OCH.sub.3 O CH i-C.sub.3 H.sub.7 OCH(CH.sub.3)COOCH.sub.2 CCH 85212 Cl " " " " "213 CH.sub.3 " " " " "214 NHCH.sub.3 " " " " "215 OCH.sub.3 " S " " "216 Cl " " " " "217 CH.sub.3 " " " " "218 NHCH.sub.3 " " " " "219 OCH.sub.3 " " N " "220 " " O " " "221 " " " " t-Bu "222 Cl " " " " "223 CH.sub.3 " " " " "224 NHCH.sub.3 " " " " "225 OCH.sub.3 " " " " "226 Cl " " " " "227 CH.sub.3 " " " " "228 NHCH.sub.3 " " " " "229 OCH.sub.3 " " N " "230 " " O " " "231 " " " CH cyclopentyl " oil232 Cl " " " " "233 CH.sub.3 " " " " "234 NHCH.sub.3 " " " " "235 OCH.sub.3 " S " " "236 Cl " " " " "237 CH.sub.3 " " " " "238 NHCH.sub.3 " " " " "239 OCH.sub.3 " " N " "240 " " O " " "241 OCH.sub.3 OCH.sub.3 O CH i-C.sub.3 H.sub.7 OCH(CH.sub.3)COOCH.sub.2 Ph242 Cl " " " " "243 CH.sub.3 " " " " "244 NHCH.sub.3 " " " " "245 OCH.sub.3 " S " " "246 Cl " " " " "247 CH.sub.3 " " " " "248 NHCH.sub.3 " " " " "249 OCH.sub.3 " " N " "250 " " O " " "251 " " " " t-Bu "252 Cl " " " " "253 CH.sub.3 " " " " "254 NHCH.sub.3 " " " " "255 OCH.sub.3 " " " " "256 Cl " " " " "257 CH.sub.3 " " " " "258 NHCH.sub.3 " " " " "259 OCH.sub.3 " " N " "260 " " O " " "261 " " " CH cyclopentyl "262 Cl " " " " "263 CH.sub.3 " " " " "264 NHCH.sub.3 " " " " "265 OCH.sub.3 " S " " "266 Cl " " " " "267 CH.sub.3 " " " " "268 NHCH.sub.3 " " " " "269 OCH.sub.3 " " N " "270 " " O " " "271 OCH.sub.3 OCH.sub.3 O CH i-C.sub.3 H.sub.7 OCH(CH.sub.3)COSCH.sub.3272 Cl " " " " "273 CH.sub.3 " " " " "274 NHCH.sub.3 " " " " "275 OCH.sub.3 " S " " "276 Cl " " " " "277 CH.sub.3 " " " " "278 NHCH.sub.3 " " " " "279 OCH.sub.3 " " N " "280 " " O " " "281 " " " " t-Bu "282 Cl " " " " "283 CH.sub.3 " " " " "284 NHCH.sub.3 " " " " "285 OCH.sub.3 " " " " "286 Cl " " " " "287 CH.sub.3 " " " " "288 NHCH.sub.3 " " " " "289 OCH.sub.3 " " N " "290 " " O " " "291 " " " CH cyclopentyl "292 Cl " " " " "293 CH.sub.3 " " " " "294 NHCH.sub.3 " " " " "295 OCH.sub.3 " S " " "296 Cl " " " " "297 CH.sub.3 " " " " "298 NHCH.sub.3 " " " " "299 OCH.sub.3 " " N " "300 " " O " " "301 OCH.sub.3 OCH.sub.3 O CH i-C.sub.3 H.sub.7 OCH(CH.sub.3)COSC.sub.2 H.sub.5302 Cl " " " " "303 CH.sub.3 " " " " "304 NHCH.sub.3 " " " " "305 OCH.sub.3 " S " " "306 Cl " " " " "307 CH.sub.3 " " " " "308 NHCH.sub.3 " " " " "309 OCH.sub.3 " " N " "310 " " O " " "311 " " " " t-Bu "312 Cl " " " " "313 CH.sub.3 " " " " "314 NHCH.sub.3 " " " " "315 OCH.sub.3 " " " " "316 Cl " " " " "317 CH.sub.3 " " " " "318 NHCH.sub.3 " " " " "319 OCH.sub.3 " " N " "320 " " O " " "321 " " " CH cyclopentyl "322 Cl " " " " "323 CH.sub.3 " " " " "324 NHCH.sub.3 " " " " "325 OCH.sub.3 " S " " "326 Cl " " " " "327 CH.sub.3 " " " " "328 NHCH.sub.3 " " " " "329 OCH.sub.3 " " N " "330 " " O " " "331 OCH.sub.3 OCH.sub.3 O CH i-C.sub.3 H.sub.7 OCH(CH.sub.2)COSCH.sub.2 Ph332 Cl " " " " "333 CH.sub.3 " " " " "334 NHCH.sub.3 " " " " "335 OCH.sub.3 " S " " "336 Cl " " " " "337 CH.sub.3 " " " " "338 NHCH.sub.3 " " " " "339 OCH.sub.3 " " N " "340 " " O " " "341 " " " " t-Bu "342 Cl " " " " "343 CH.sub.3 " " " " "344 NHCH.sub.3 " " " " "345 OCH.sub.3 " " " " " "346 Cl " " " " "347 CH.sub.3 " " " " "348 NHCH.sub.3 " " " " "349 OCH.sub.3 " " N " "350 " " O " " "351 " " " CH cyclopentyl "352 Cl " " " " "353 CH.sub.3 " " " " "354 NHCH.sub.3 " " " " "355 OCH.sub.3 " S " " "356 Cl " " " " "357 CH.sub.3 " " " " "358 NHCH.sub.3 " " " " "359 OCH.sub.3 " " N " "360 " " O " " "361 OCH.sub.3 OCH.sub.3 O CH i-C.sub.3 H.sub.7 ##STR24## 131362 Cl " " " " "363 CH.sub.3 " " " " "364 NHCH.sub.3 " " " " "365 OCH.sub.3 " S " " "366 Cl " " " " "367 CH.sub.3 " " " " "368 NHCH.sub.3 " " " " "369 OCH.sub.3 " " N " "370 " " O " " "371 " " " " t-Bu "372 Cl " " " " "373 CH.sub.3 " " " " "374 NHCH.sub.3 " " " " "375 OCH.sub.3 " " " " "376 Cl " " " " "377 CH.sub.3 " " " " "378 NHCH.sub.3 " " " " "379 OCH.sub.3 " " N " "380 " " O " " "381 " " " CH cyclopentyl "382 Cl " " " " "383 CH.sub.3 " " " " "384 NHCH.sub.3 " " " " "385 OCH.sub.3 " S " " "386 Cl " " " "387 CH.sub.3 " " " " "388 NHCH.sub.3 " " " " "389 OCH.sub.3 " " N " "390 " " O " " "391 OCH.sub.3 OCH.sub.3 O CH i-C.sub.3 H.sub.7 OCH.sub.2 Si(CH.sub.3).sub.3 oil392 Cl " " " " "393 CH.sub.3 " " " " "394 NHCH.sub.3 " " " " "395 OCH.sub.3 " S " " "396 Cl " " " " "397 CH.sub.3 " " " " "398 NHCH.sub.3 " " " " "399 OCH.sub.3 " " N " "400 " " O " " "401 " " " " t-Bu "402 Cl " " " " "403 CH.sub.3 " " " " "404 NHCH.sub.3 " " " " "405 OCH.sub.3 " " " " "406 Cl " " " " "407 CH.sub.3 " " " " "408 NHCH.sub.3 " " " " "409 OCH.sub.3 " " N " "410 " " O " " " "411 " " " CH cyclopentyl "412 Cl " " " " "413 CH.sub.3 " " " " "414 NHCH.sub.3 " " " " "415 OCH.sub.3 " S " " "416 Cl " " " " "417 CH.sub.3 " " " " "418 NHCH.sub.3 " " " " "419 OCH.sub.3 " " N " "420 " " O " " " "421 OCH.sub.3 OCH.sub.3 O CH i-C.sub.3 H.sub.7 pyrid-2-ylmethoxy422 Cl " " " " "423 CH.sub.3 " " " " "424 NHCH.sub.3 " " " " "425 OCH.sub.3 " S " " "426 Cl " " " " "427 CH.sub.3 " " " " "428 NHCH.sub.3 " " " " "429 OCH.sub.3 " " N " "430 " " O " " "431 " " " " t-Bu "432 Cl " " " " "433 CH.sub.3 " " " " "434 NHCH.sub.3 " " " " "435 OCH.sub.3 " " " " "436 Cl " " " " "437 CH.sub.3 " " " " "438 NHCH.sub.3 " " " " "439 OCH.sub.3 " " N " "440 " " O " " "441 " " " CH cyclopentyl " 88-90442 Cl " " " " "443 CH.sub.3 " " " " "444 NHCH.sub.3 " " " " "445 OCH.sub.3 " S " " "446 Cl " " " " "447 CH.sub.3 " " " " "448 NHCH.sub.3 " " " " "449 OCH.sub.3 " " N " "450 " " O " " "451 OCH.sub.3 OCH.sub.3 O CH i-C.sub.3 H.sub.7 pyrid-3-ylmethoxy452 Cl " " " " "453 CH.sub.3 " " " " "454 NHCH.sub.3 " " " " "455 OCH.sub.3 " S " " "456 Cl " " " " "457 CH.sub.3 " " " " "458 NHCH.sub.3 " " " " "459 OCH.sub.3 " " N " "460 " " O " " "461 " " " " t-Bu "462 Cl " " " " "463 CH.sub.3 " " " " "464 NHCH.sub.3 " " " " "465 OCH.sub.3 " " " " "466 Cl " " " " "467 CH.sub.3 " " " " "468 NHCH.sub.3 " " " " "469 OCH.sub.3 " " N " "470 " " O " " "471 " " " CH cyclopentyl "472 Cl " " " " "473 CH.sub.3 " " " " "474 NHCH.sub.3 " " " " "475 OCH.sub.3 " S " " "476 Cl " " " " "477 CH.sub.3 " " " " "478 NHCH.sub.3 " " " " "479 OCH.sub.3 " " N " "480 " " O " " "481 OCH.sub.3 OCH.sub.3 O CH i-C.sub.3 H.sub.7 OCH.sub.2 P(O)(CH.sub.3).sub.2482 Cl " " " " "483 CH.sub.3 " " " " "484 NHCH.sub.3 " " " " "485 OCH.sub.3 " S " " "486 Cl " " " " "487 CH.sub.3 " " " " "488 NHCH.sub.3 " " " " "489 OCH.sub.3 " " N " "490 " " O " " "491 " " " " t-Bu "492 Cl " " " " "493 CH.sub.3 " " " " "494 NHCH.sub.3 " " " " "495 OCH.sub.3 " " " " "496 Cl " " " " "497 CH.sub.3 " " " " "498 NHCH.sub.3 " " " " "499 OCH.sub.3 " " N " "500 " " O " " "501 " " " CH cyclopentyl " oil502 Cl " " " " "503 CH.sub.3 " " " " "504 NHCH.sub.3 " " " " "505 OCH.sub.3 " S " " "506 Cl " " " " "507 CH.sub.3 " " " " "508 NHCH.sub.3 " " " " "509 OCH.sub.3 " " N " "510 " " O " " "511 OCH.sub.3 OCH.sub.3 O CH i-C.sub. 3 H.sub.7 OSi(CH.sub.3).sub.2 (t-Bu) oil512 Cl " " " " "513 CH.sub.3 " " " " "514 NHCH.sub.3 " " " " "515 OCH.sub.3 " S " " "516 Cl " " " " "517 CH.sub.3 " " " " "518 NHCH.sub.3 " " " " "519 OCH.sub.3 " " N " "520 " " O " " "521 " " " " t-Bu "522 Cl " " " " "523 CH.sub.3 " " " " "524 NHCH.sub.3 " " " " "525 OCH.sub.3 " " " " "526 Cl " " " " "527 CH.sub.3 " " " " "528 NHCH.sub.3 " " " " "529 OCH.sub.3 " " N " "530 " " O " " "531 " " " CH cyclopentyl "532 Cl " " " " "533 CH.sub.3 " " " " "534 NHCH.sub.3 " " " " "535 OCH.sub.3 " S " " "536 Cl " " " " "537 CH.sub.3 " " " " "538 NHCH.sub.3 " " " " "539 OCH.sub.3 " " N " "540 " " O " " "541 OCH.sub.3 OCH.sub.3 O CH i-C.sub.3 H.sub.7 OSi(i-Pr).sub.3 1.4800542 Cl " " " " "543 CH.sub.3 " " " " "544 NHCH.sub.3 " " " " "545 OCH.sub.3 " S " " "546 Cl " " " " "547 CH.sub.3 " " " " "548 NHCH.sub.3 " " " " "549 OCH.sub.3 " " N " "550 " " O " " "551 " " " " t-Bu "552 Cl " " " " "553 CH.sub.3 " " " " "554 NHCH.sub.3 " " " " "555 OCH.sub. 3 " " " " "556 Cl " " " " "557 CH.sub.3 " " " " "558 NHCH.sub.3 " " " " "559 OCH.sub.3 " " N " "560 " " O " " "561 " " " CH cyclopentyl "562 Cl " " " " "563 CH.sub.3 " " " " "564 NHCH.sub.3 " " " " "565 OCH.sub.3 " S " " "566 Cl " " " " "567 CH.sub.3 " " " " "568 NHCH.sub.3 " " " " "569 OCH.sub.3 " " N " "570 " " O " " "571 OCH.sub.3 OCH.sub.3 O CH i-C.sub.3 H.sub.7 OCH.sub.2 C(OCH.sub.3)CHCOOCH.sub.3 77-78572 Cl " " " " "573 CH.sub.3 " " " " "574 NHCH.sub.3 " " " " "575 OCH.sub.3 " S " " "576 Cl " " " " "577 CH.sub.3 " " " " "578 NHCH.sub.3 " " " " "579 OCH.sub.3 " " N " "580 " " O " " "581 " " " " t-Bu "582 Cl " " " " "583 CH.sub.3 " " " " "584 NHCH.sub.3 " " " " "585 OCH.sub.3 " " " " "586 Cl " " " " "587 CH.sub.3 " " " " "588 NHCH.sub.3 " " " " "589 OCH.sub.3 " " N " "590 " " O " " "591 " " " CH cyclopentyl " 72-74592 Cl " " " " "593 CH.sub.3 " " " " "594 NHCH.sub.3 " " " " "595 OCH.sub.3 " S " " "596 Cl " " " " "597 CH.sub.3 " " " " "598 NHCH.sub.3 " " " " "599 OCH.sub.3 " " N " "600 " " O " " "601 OCH.sub.3 OCH.sub.3 O CH i-C.sub.3 H.sub.7 OCH.sub.2 COOCH.sub.2 COOCH.sub.3 oil602 Cl " " " " "603 CH.sub.3 " " " " "604 NHCH.sub.3 " " " " "605 OCH.sub.3 " S " " "606 Cl " " " " "607 CH.sub.3 " " " " "608 NHCH.sub.3 " " " " "609 OCH.sub.3 " " N " "610 " " O " " "611 " " " " t-Bu "612 Cl " " " " "613 CH.sub.3 " " " " "614 NHCH.sub.3 " " " " "615 OCH.sub.3 " " " " "616 Cl " " " " "617 CH.sub.3 " " " " "618 NHCH.sub.3 " " " " "619 OCH.sub.3 " " N " "620 " " O " " "621 " " " CH cyclopentyl " 72-74622 Cl " " " " "623 CH.sub.3 " " " " "624 NHCH.sub.3 " " " " "625 OCH.sub.3 " S " " "626 Cl " " " " "627 CH.sub.3 " " " " "628 NHCH.sub.3 " " " " "629 OCH.sub.3 " " N " "630 " " O " " "631 OCH.sub.3 OCH.sub.3 O CH i-C.sub.3 H.sub.7 OCH.sub.2 SO.sub.2 CH.sub.3 108-110632 Cl " " " " "633 CH.sub.3 " " " " "634 NHCH.sub.3 " " " " "635 OCH.sub.3 " S " " "636 Cl " " " " "637 CH.sub.3 " " " " "638 NHCH.sub.3 " " " " "639 OCH.sub.3 " " N " "640 " " O " " "641 " " " " t-Bu "642 Cl " " " " "643 CH.sub.3 " " " " "644 NHCH.sub.3 " " " " "645 OCH.sub.3 " " " " "646 Cl " " " " "647 CH.sub.3 " " " " "648 NHCH.sub.3 " " " " "649 OCH.sub.3 " " N " "650 " " O " " "651 " " " CH cyclopentyl "652 Cl " " " " "653 CH.sub.3 " " " " "654 NHCH.sub.3 " " " " "655 OCH.sub.3 " S " " "656 Cl " " " " "657 CH.sub.3 " " " " "658 NHCH.sub.3 " " " " "659 OCH.sub.3 " " N " "660 " " O " " "661 OCH.sub.3 OCH.sub.3 O CH i-C.sub.3 H.sub.7 OCH.sub.2 S(O)CH.sub.2 CH.sub.3662 Cl " " " " "663 CH.sub.3 " " " " "664 NHCH.sub.3 " " " " "665 OCH.sub.3 " S " " "666 Cl " " " " "667 CH.sub.3 " " " " "668 NHCH.sub.3 " " " " "669 OCH.sub.3 " " N " "670 " " O " " "671 " " " " t-Bu "672 Cl " " " " "673 CH.sub.3 " " " " "674 NHCH.sub.3 " " " " "675 OCH.sub.3 " S " " "676 Cl " " " " "677 CH.sub.3 " " " " "678 NHCH.sub.3 " " " " "679 OCH.sub.3 " " N " "680 " " O " " "681 " " " CH cyclopentyl "682 Cl " " " " "683 CH.sub.3 " " " " "684 NHCH.sub.3 " " " " "685 OCH.sub.3 " S " " "686 Cl " " " " "687 CH.sub.3 " " " " "688 NHCH.sub.3 " " " " "689 OCH.sub.3 " " N " "690 " " O " " "691 OCH.sub.3 OCH.sub.3 O CH i-C.sub.3 H.sub.7 OCH.sub.2 SOCH.sub.3 76-78692 Cl " " " " "693 CH.sub.3 " " " " "694 NHCH.sub.3 " " " " "695 OCH.sub.3 " S " " "696 Cl " " " " "697 CH.sub.3 " " " " "698 NHCH.sub.3 " " " " "699 OCH.sub.3 " " N " "700 " " O " " "701 " " " " t-Bu "702 Cl " " " " "703 CH.sub.3 " " " " "704 NHCH.sub.3 " " " " "705 OCH.sub.3 " " " " "706 Cl " " " " "707 CH.sub.3 " " " " "708 NHCH.sub.3 " " " " "709 OCH.sub.3 " " N " "710 " " O " " "711 " " " CH cyclopentyl "712 Cl " " " " "713 CH.sub.3 " " " " "714 NHCH.sub.3 " " " " "715 OCH.sub.3 " S " " "716 Cl " " " " "717 CH.sub.3 " " " " "718 NHCH.sub.3 " " " " "719 OCH.sub.3 " " N " "720 " " O " " "721 OCH.sub.3 OCH.sub.3 O CH i-C.sub.3 H.sub.7 OCH.sub.2 SO.sub.2 C.sub.2 H.sub.5722 Cl " " " " "723 CH.sub.3 " " " " "724 NHCH.sub.3 " " " " "725 OCH.sub.3 " S " " "726 Cl " " " " "727 CH.sub.3 " " " " "728 NHCH.sub.3 " " " " "729 OCH.sub.3 " " N " "730 " " O " " "731 " " " " t-Bu "732 Cl " " " " "733 CH.sub.3 " " " " "734 NHCH.sub.3 " " " " "735 OCH.sub.3 " " " " "736 Cl " " " " "737 CH.sub.3 " " " " "738 NHCH.sub.3 " " " " "739 OCH.sub.3 " " N " "740 " " O " " "741 " " " CH cyclopentyl "742 Cl " " " " "743 CH.sub.3 " " " " "744 NHCH.sub.3 " " " " "745 OCH.sub.3 " S " " "746 Cl " " " " "747 CH.sub.3 " " " " "748 NHCH.sub.3 " " " " "749 OCH.sub.3 " " N " "750 " " O " " "751 OCH.sub.3 OCH.sub.3 O CH i-C.sub.3 H.sub.7 OCH.sub.2 CH.sub.2 SO.sub.2 C.sub.2 H.sub.5752 Cl " " " " "753 CH.sub.3 " " " " "754 NHCH.sub.3 " " " " "755 OCH.sub.3 " S " " "756 Cl " " " " "757 CH.sub.3 " " " " "758 NHCH.sub.3 " " " " "759 OCH.sub.3 " " N " "760 " " O " " "761 " " " " t-Bu "762 Cl " " " " "763 CH.sub.3 " " " " "764 NHCH.sub.3 " " " " "765 OCH.sub.3 " " " " "766 Cl " " " " "767 CH.sub.3 " " " " "768 NHCH.sub.3 " " " " "769 OCH.sub.3 " " N " "770 " " O " " "771 " " " CH cyclopentyl "772 Cl " " " " "773 CH.sub.3 " " " " "774 NHCH.sub.3 " " " " "775 OCH.sub.3 " S " " "776 Cl " " " " "777 CH.sub.3 " " " " "778 NHCH.sub.3 " " " " "779 OCH.sub.3 " " N " "780 " " O " " "781 OCH.sub.3 OCH.sub.3 O CH i-C.sub.3 H.sub.7 OC.sub.3 H.sub.6 OCH.sub.2 CHCH.sub.2782 Cl " " " " "783 CH.sub.3 " " " " "784 NHCH.sub.3 " " " " "785 OCH.sub.3 " S " " "786 Cl " " " " "787 CH.sub.3 " " " " "788 NHCH.sub.3 " " " " "789 OCH.sub.3 " " N " "790 " " O " " "791 " " " " t-Bu "792 Cl " " " " "793 CH.sub.3 " " " " "794 NHCH.sub.3 " " " " "795 OCH.sub.3 " " " " "796 Cl " " " " "797 CH.sub.3 " " " " "798 NHCH.sub.3 " " " " "799 OCH.sub.3 " " N " "800 " " O " " "801 " " " CH cyclopentyl "802 Cl " " " " "803 CH.sub.3 " " " " "804 NHCH.sub.3 " " " " "805 OCH.sub.3 " S " " "806 Cl " " " " "807 CH.sub.3 " " " " "808 NHCH.sub.3 " " " " "809 OCH.sub.3 " " N " "810 " " O " " "811 OCH.sub.3 OCH.sub.3 O CH i-C.sub.3 H.sub.7 OCH.sub.2 CH.sub.2 OCH.sub.2 Ph812 Cl " " " " "813 CH.sub.3 " " " " "814 NHCH.sub.3 " " " " "815 OCH.sub.3 " S " " "816 Cl " " " " "817 CH.sub.3 " " " " "818 NHCH.sub.3 " " " " "819 OCH.sub.3 " " N " "820 " " O " " "821 " " " " t-Bu "822 Cl " " " " "823 CH.sub.3 " " " " "824 NHCH.sub.3 " " " " "825 OCH.sub.3 " " " " "826 Cl " " " " "827 CH.sub.3 " " " " "828 NHCH.sub.3 " " " " "829 OCH.sub.3 " " N " "830 " " O " " "831 " " " CH cyclopentyl "832 Cl " " " " "833 CH.sub.3 " " " " "834 NHCH.sub.3 " " " " "835 OCH.sub.3 " S " " "836 Cl " " " " "837 CH.sub.3 " " " " "838 NHCH.sub.3 " " " " "839 OCH.sub.3 " " N " "840 " " O " " "841 OCH.sub.3 OCH.sub.3 O CH i-C.sub.3 H.sub.7 OCH.sub.2 CH.sub.2 OCH.sub.2 CCH842 Cl " " " " "843 CH.sub.3 " " " " "844 NHCH.sub.3 " " " " "845 OCH.sub.3 " S " " "846 Cl " " " " "847 CH.sub.3 " " " " "848 NHCH.sub.3 " " " " "849 OCH.sub.3 " " N " "850 " " O " " "851 " " " " t-Bu "852 Cl " " " " "853 CH.sub.3 " " " " "854 NHCH.sub.3 " " " " "855 OCH.sub.3 " " " " "856 Cl " " " " "857 CH.sub.3 " " " " "858 NHCH.sub.3 " " " " "859 OCH.sub.3 " " N " "860 " " O " " "861 " " " CH cyclopentyl "862 Cl " " " " "863 CH.sub.3 " " " " "864 NHCH.sub.3 " " " " "865 OCH.sub.3 " S " " "866 Cl " " " " "867 CH.sub.3 " " " " "868 NHCH.sub.3 " " " " "869 OCH.sub.3 " " N " "870 " " O " " "871 OCH.sub.3 OCH.sub.3 O CH i-C.sub.3 H.sub.7 OCH.sub.2 CH(CH.sub.3) OCH.sub.2 CHCH.sub.2 oil872 Cl " " " " "873 CH.sub.3 " " " " "874 NHCH.sub.3 " " " " "875 OCH.sub.3 " S " " "876 Cl " " " " "877 CH.sub.3 " " " " "878 NHCH.sub.3 " " " " "879 OCH.sub.3 " " N " "880 " " O " " "881 " " " " t-Bu "882 Cl " " " " "883 CH.sub.3 " " " " "884 NHCH.sub.3 " " " " "885 OCH.sub.3 " " " " "886 Cl " " " " "887 CH.sub.3 " " " " "888 NHCH.sub.3 " " " " "889 OCH.sub.3 " " N " "890 " " O " " "891 " " " CH cyclopentyl " oil892 Cl " " " " "893 CH.sub.3 " " " " "894 NHCH.sub.3 " " " " "895 OCH.sub.3 " S " " "896 Cl " " " " "897 CH.sub.3 " " " " "898 NHCH.sub.3 " " " " "899 OCH.sub.3 " " N " "900 " " O " " "901 OCH.sub.3 OCH.sub.3 O CH i-C.sub.3 H.sub.7 OC.sub.4 H.sub.8 OCH.sub.2 CHCH.sub.2902 Cl " " " " "903 CH.sub.3 " " " " "904 NHCH.sub.3 " " " " "905 OCH.sub.3 " S " " "906 Cl " " " " "907 CH.sub.3 " " " " "908 NHCH.sub.3 " " " " "909 OCH.sub.3 " " N " "910 " " O " " "911 " " " " t-Bu "912 Cl " " " " "913 CH.sub.3 " " " " "914 NHCH.sub.3 " " " " "915 OCH.sub.3 " " " " "916 Cl " " " " "917 CH.sub.3 " " " " "918 NHCH.sub.3 " " " " "919 OCH.sub.3 " " N " "920 " " O " " "921 " " " CH cyclopentyl "922 Cl " " " " "923 CH.sub.3 " " " " "924 NHCH.sub.3 " " " " "925 OCH.sub.3 " S " " "926 Cl " " " " "927 CH.sub.3 " " " " "928 NHCH.sub.3 " " " " "929 OCH.sub.3 " " N " "930 " " O " " "931 OCH.sub.3 OCH.sub.3 O CH i-C.sub.3 H.sub.7 OCH.sub.2 COONC(CH.sub.3).sub.2932 Cl " " " " "933 CH.sub.3 " " " " "934 NHCH.sub.3 " " " " "935 OCH.sub.3 " S " " "936 Cl " " " " "937 CH.sub.3 " " " " "938 NHCH.sub.3 " " " " "939 OCH.sub.3 " " N " "940 " " O " " "941 " " " " t-Bu "942 Cl " " " " "943 CH.sub.3 " " " " "944 NHCH.sub.3 " " " " "945 OCH.sub.3 " " " " "946 Cl " " " " "947 CH.sub.3 " " " " "948 NHCH.sub.3 " " " " "949 OCH.sub.3 " " N " "950 " " O " " "951 " " " CH cyclopentyl "952 Cl " " " " "953 CH.sub.3 " " " " "954 NHCH.sub.3 " " " " "955 OCH.sub.3 " S " " "956 Cl " " " " "957 CH.sub.3 " " " " "958 NHCH.sub.3 " " " " "959 OCH.sub.3 " " N " "960 " " O " " "961 OCH.sub.3 OCH.sub.3 O CH i-C.sub.3 H.sub.7 OCH(CH.sub.3)CONC(CH.sub.3).sub.2962 Cl " " " " "963 CH.sub.3 " " " " "964 NHCH.sub.3 " " " " "965 OCH.sub.3 " S " " "966 Cl " " " " "967 CH.sub.3 " " " " "968 NHCH.sub.3 " " " " "969 OCH.sub.3 " " N " "970 " " O " " "971 " " " " t-Bu "972 Cl " " " " "973 CH.sub.3 " " " " "974 NHCH.sub.3 " " " " "975 OCH.sub.3 " " " " "976 Cl " " " " "977 CH.sub.3 " " " " "978 NHCH.sub.3 " " " " "979 OCH.sub.3 " " N " "980 " " O " " "981 " " " CH cyclopentyl "982 Cl " " " " "983 CH.sub.3 " " " " "984 NHCH.sub.3 " " " " "985 OCH.sub.3 " S " " "986 Cl " " " " "987 CH.sub.3 " " " " "988 NHCH.sub.3 " " " " "989 OCH.sub.3 " " N " "990 " " O " " "991 OCH.sub.3 OCH.sub.3 O CH i-C.sub.3 H.sub.7 NHCH.sub.2 COOCH.sub.2 CHCH.sub.2992 Cl " " " " "993 CH.sub.3 " " " " "994 NHCH.sub.3 " " " " "995 OCH.sub.3 " S " " "996 Cl " " " " "997 CH.sub.3 " " " " "998 NHCH.sub.3 " " " " "999 OCH.sub.3 " " N " "1000 " " O " " "1001 " " " " t-Bu "1002 Cl " " " " "1003 CH.sub.3 " " " " "1004 NHCH.sub.3 " " " " "1005 OCH.sub.3 " S " " "1006 Cl " " " " "1007 CH.sub.3 " " " " "1008 NHCH.sub.3 " " " " "1009 OCH.sub.3 " " N " "1010 " " O " " "1011 " " " CH cyclopentyl "1012 Cl " " " " "1013 CH.sub.3 " " " " "1014 NHCH.sub.3 " " " " "1015 OCH.sub.3 " S " " "1016 Cl " " " " "1017 CH.sub.3 " " " " "1018 NHCH.sub.3 " " " " "1019 OCH.sub.3 " " N " "1020 " " O " " "1021 OCH.sub.3 OCH.sub.3 O CH i-C.sub.3 H.sub.7 NHCH.sub.2 COOCH.sub.2 CCH1022 Cl " " " " "1023 CH.sub.3 " " " " "1024 NHCH.sub.3 " " " " "1025 OCH.sub.3 " S " " "1026 Cl " " " " "1027 CH.sub.3 " " " " "1028 NHCH.sub.3 " " " " "1029 OCH.sub.3 " " N " "1030 " " O " " "1031 " " " " t-Bu "1032 Cl " " " " "1033 CH.sub.3 " " " " "1034 NHCH.sub.3 " " " " "1035 OCH.sub.3 " " " " "1036 Cl " " " " "1037 CH.sub.3 " " " " "1038 NHCH.sub.3 " " " " "1039 OCH.sub.3 " " N " "1040 " " O " " "1041 " " " CH cyclopentyl "1042 Cl " " " " "1043 CH.sub.3 " " " " "1044 NHCH.sub.3 " " " " "1045 OCH.sub.3 " S " " "1046 Cl " " " " "1047 CH.sub.3 " " " " "1048 NHCH.sub.3 " " " " "1049 OCH.sub.3 " " N " "1050 " " O " " "1051 OCH.sub.3 OCH.sub.3 O CH i-C.sub.3 H.sub.7 NHCH(CH.sub.3)COSCH.sub.2 Ph1052 Cl " " " " "1053 CH.sub.3 " " " " "1054 NHCH.sub.3 " " " " "1055 OCH.sub.3 " S " " "1056 Cl " " " " "1057 CH.sub.3 " " " " "1058 NHCH.sub.3 " " " " "1059 OCH.sub.3 " " N " "1060 " " O " " "1061 " " " " t-Bu "1062 Cl " " " " "1063 CH.sub.3 " " " " "1064 NHCH.sub.3 " " " " "1065 OCH.sub.3 " " " " "1066 Cl " " " " "1067 CH.sub.3 " " " " "1068 NHCH.sub.3 " " " " "1069 OCH.sub.3 " " N " "1070 " " O " " "1071 " " " CH cyclopentyl "1072 Cl " " " " "1073 CH.sub.3 " " " " "1074 NHCH.sub.3 " " " " "1075 OCH.sub.3 " S " " "1076 Cl " " " " "1077 CH.sub.3 " " " " "1078 NHCH.sub.3 " " " " "1079 OCH.sub.3 " " N " "1080 " " O " " "1081 OCH.sub.3 OCH.sub.3 O CH i-C.sub.3 H.sub.7 OCH(t-Bu)(CN) 90-921082 Cl " " " " "1083 CH.sub.3 " " " " "1084 NHCH.sub.3 " " " " "1085 OCH.sub.3 " S " " "1086 Cl " " " " "1087 CH.sub.3 " " " " "1088 NHCH.sub.3 " " " " "1089 OCH.sub.3 " " N " "1090 " " O " " "1091 " " " " t-Bu "1092 Cl " " " " "1093 CH.sub.3 " " " " "1094 NHCH.sub.3 " " " " "1095 OCH.sub.3 " " " " "1096 Cl " " " " "1097 CH.sub.3 " " " " "1098 NHCH.sub.3 " " " " "1099 OCH.sub.3 " " N " "1100 " " O " " "1101 " " " CH cyclopentyl "1102 Cl " " " " "1103 CH.sub.3 " " " " "1104 NHCH.sub. 3 " " " " "1105 OCH.sub.3 " S " " "1106 Cl " " " " "1107 CH.sub.3 " " " " "1108 NHCH.sub.3 " " " " "1109 OCH.sub.3 " " N " "1110 " " O " " "1111 OCH.sub.3 OCH.sub.3 O CH i-C.sub.3 H.sub.7 OCH(CH.sub.3)CN1112 Cl " " " " "1113 CH.sub.3 " " " " "1114 NHCH.sub.3 " " " " "1115 OCH.sub.3 " S " " "1116 Cl " " " " "1117 CH.sub.3 " " " " "1118 NHCH.sub.3 " " " " "1119 OCH.sub.3 " " N " "1120 " " O " " "1121 " " " " t-Bu "1122 Cl " " " " "1123 CH.sub.3 " " " " "1124 NHCH.sub.3 " " " " "1125 OCH.sub.3 " " " " "1126 Cl " " " " "1127 CH.sub.3 " " " " "1128 NHCH.sub.3 " " " " "1129 OCH.sub.3 " " N " "1130 " " O " " "1131 " " " CH cyclopentyl "1132 Cl " " " " "1133 CH.sub.3 " " " " "1134 NHCH.sub.3 " " " " "1135 OCH.sub.3 " S " " "1136 Cl " " " " "1137 CH.sub.3 " " " " "1138 NHCH.sub.3 " " " " "1139 OCH.sub.3 " " N " "1140 OCH.sub.3 OCH.sub.3 O N cyclopentyl OCH(CH.sub.3)CN1141 " " " CH i-Pr ##STR25## Ol__________________________________________________________________________Note: In Table I, Ph = phenyl, Pr = propyl and Bu = butyl.

BIOLOGICAL EXAMPLES

The damage to the weed plants, or the crop plant compatibility, was rated using a key in which the effectiveness is expressed by scores from 0 to 5.In this key,

0=no action 1=0 to 20% action or damage 2=20 to 40% action or damage 3=40 to 60% action or damage 4=60 to 80% action or damage 5=80 to 100% action or damage

1. Pre-emergence herbicidal action

Seeds or rhizome pieces of mono- and dicotyledon weed plants were placed inplastic pots containing sandy loam soil and covered with soil. Various dosage rates of the compounds according to the invention formulated in theform of wettable powders or emulsion concentrates were then applied to the surface of the soil cover in the form of an aqueous suspension or emulsionat a water application rate of 600 to 800 l/ha (converted).

After the treatment, the pots were placed in the greenhouse and kept under good growth conditions for the weeds. Optical rating of the plant damage, or inadequate emergence, was effected after the test plants had emerged after a trial time of 3 to 4 weeks in comparison with untreated controls. As shown by the score figures in Table 3, the compounds according to the invention have a good herbicidal pre-emergence activity against a broad range of grass weeds and broad-leaf weeds.

TABLE II______________________________________Pre-emergence actionDosage rate Herbicidal actionEx. No. (kg of a.i./ha) STAL STME ECCR LOMU______________________________________ 31 1.25 5 5 5 5181 0.3 5 5 5 5211 0.3 5 5 5 5 1 0.3 5 5 5 5571 0.3 5 5 5 5361 0.3 5 5 5 5391 0.3 5 5 4 4511 0.3 5 5 5 5______________________________________Abbreviations:STAL = Sinapis alba-STME = Stellaria media-ECCR = Echinochloa crus-galli-LOMU = Lolium multiflorum-a.i. = active ingredient

2. Post-emergence herbicidal action

Seeds or rhizome pieces of mono- and dicotyledon weeds were placed in plastic pots containing sandy loam soil, covered with soil and grown in the greenhouse under good growth conditions. Three weeks after sowing, thetest plants were treated at the three-leaf stage.

Various dosage rates of the compounds according to the invention formulatedas wettable powders or emulsion concentrates were sprayed on the green parts of the plants at a water application rate of 600 to 800 l/ha (converted), and, after the test plants had remained in the greenhouse forapprox. 3 to 4 weeks under ideal growth conditions, the action of the preparations was scored visually in comparison rated with untreated controls.

The compositions according to the invention also have a good herbicidal activity against a broad range of economically important grass weeds and broad-leaf weeds when used post-emergence.

TABLE III______________________________________Post-emergence actionDosage rate Herbicidal actionEx. No. (kg of a.i./ha) STAL STME ECCR LOMU______________________________________ 31 1.25 5 5 5 5181 0.3 5 5 5 5211 0.3 5 4 5 5 1 0.3 5 5 5 5571 0.3 4 4 3 5361 0.3 5 5 5 5391 0.3 5 5 4 4511 0.3 5 5 5 5______________________________________Abbreviations: as in Table II

Claims

1. A compound of the formula (I) ##STR26## in which A is a radical formula ##STR27## X is O or S, Y is CH,

R.sup.1, R.sup.2 independently of one another are C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, halogen, C.sub.1 -C.sub.4 -haloalkoxy, C.sub.1 -C.sub.4 -alkylamino or di-(C.sub.1 -C.sub.4 -alkyl)amino,

R.sup.3 is isopropyl, tert-butyl or cyclopentyl,

R.sup.4 is a C.sub.1 -C.sub.4 -alkoxy radical which is

substituted by C.sub.2 -C.sub.4 -alkenyloxy, C.sub.2 -C.sub.4 -alkinyloxy, cyclohexyloxy, cyclohexenyloxy, cyclopentyloxy, cyclopentenyloxy, benzyloxy, benzylthio, (R*).sub.3 Si or (R*).sub.3 SiO, in which the radicals R* independently of one another are C.sub.1 -C.sub.4 -alkyl, C.sub.2 -C.sub.4 -alkenyl, C.sub.2 -C.sub.4 -alkinyl or phenyl, or by cyano, nitro, (C.sub.1 -C.sub.4 -alkyl)-carbonyl, C.sub.1 -C.sub.4 -alkylsulfonyl, C.sub.1 -C.sub.4 -alkylsulfinyl, di

(C.sub.1 -C.sub.4 -alkyl)-phosphoryl, di-(C.sub.1 -C.sub.4 -alkyl)-phosphonyl, di-(C.sub.1 -C.sub.4 -alkyl)-phosphinyl or pyridyl, or is a radical of a 5- or 6-membered cyclic lactone bonded through the carbon in the .alpha.-position relative to the carbonyl group, or, R.sup.4 is a radical of the formula

--D.sup.7 --CR.sup.15 R.sup.16 --L

in which

D.sup.7 is O, S, NH, methylamino or ethylamino,

R.sup.15, R.sup.16 independently of one another are hydrogen, C.sub.1 -C.sub.4 -alkyl, C.sub.2 -C.sub.4 -alkenyl, C.sub.2 -C.sub.4 -alkinyl, phenyl or benzyl,

L is an acid derivative radical of the formula

--CO--O--R.sup.17

--CO--S--R.sup.18

--CO--NR.sup.19 R.sup.20

--CO--O--N.dbd.CR.sup.21 R.sup.22

--CO--N.dbd.CR.sup.21 R.sup.22

--O--CO--R.sup.23

--S--CO--R.sup.23

--NR.sup.14 --CO--R.sup.23 ##STR28## R.sup.17 is hydrogen, C.sub.2 -C.sub.4 -alkenyl or C.sub.2 -C.sub.4 -alkinyl, cyclohexyl, cyclopentyl, cyclohexenyl, cyclopentenyl, benzyl, phenyl or phenyl substituted by one or more radicals selected from the group consisting of halogen, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -haloalkoxy, nitro and cyano, R.sup.18 is hydrogen , C.sub.1 -C.sub.4 -alkyl, C.sub.2 -C.sub.4 -alkenyl or C.sub.2 -C.sub.4 -alkinyl, cyclohexyl, cyclopentyl, cyclohexenyl, cyclopentenyl, benzyl, phenyl or phenyl substituted by one or more radicals selected from the group consisting of halogen, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 -haloalkoxy, nitro and cyano,

R.sup.19, R.sup.20 independently of one another are hydrogen, C.sub.1 -C.sub.4 -alkyl, C.sub.2 -C.sub.4 -alkenyl, C.sub.2 -C.sub.4 -alkinyl, cyclohexyl, cyclopentyl, benzyl, phenyl or phenyl substituted by one or more radicals selected from the group consisting of halogen, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -haloalkoxy, nitro and cyano, or together with the nitrogen atom linking them, are a heterocyclic 5- or 6-membered ring,

R.sup.21, R.sup.22 independently of one another are C.sub.1 -C.sub.4 -alkyl, C.sub.2 -C.sub.4 -alkenyl or C.sub.2 -C.sub.4 -alkinyl or together with the carbon atom linking them, a carbocyclic 5- or 6- membered ring,

R.sup.23 is hydrogen, C.sub.1 -C.sub.4 -alkyl, cyclohexyl, cyclopentyl, phenyl or phenyl substituted by one or more radicals selected from the group consisting of halogen, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -haloalkoxy, nitro and cyano,

R.sup.24 is C.sub.1 -C.sub.4 -alkyl, C.sub.2 -C.sub.4 -alkenyl or C.sub.2 -C.sub.4 -alkinyl, where the last-mentioned 3 radicals are unsubstituted or substituted by one or more radicals from the group consisting of halogen or C.sub.1 -C.sub.4 -alkoxy, or is C.sub.1 -C.sub.4 -alkanoyl, (C.sub.1 -C.sub.4 -alkoxy)-carbonyl, benzyl, benzoxycarbonyl, phenyl or benzoyl, where the last-membered 4 radicals are unsubstituted or substituted by C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, halogen or nitro,

R.sup.25 hydrogen or C.sub.1 -C.sub.4 -alkyl,

R.sup.26 is hydrogen, C.sub.1 -C.sub.4 -alkyl, C.sub.2 -C.sub.4 -alkenyl or C.sub.2 -C.sub.4 -alkinyl, where the last-mentioned 3 radicals are unsubstituted or substituted by one or more halogen atoms

R.sup.27, R.sup.28 independently of one another are hydrogen or C.sub.1 -C.sub.4 -alkyl, or R.sup.4 is a radical of the formula ##STR29## where R.sup.29, R.sup.30, R.sup.31 independently of one another are C.sub.1 -C.sub.4 -alkyl, C.sub.2 -C.sub.4 -alkenyl C.sub.2 -C.sub.4 -alkinyl, phenyl or phenyl substituted by one or more radicals selected from the group consisting of halogen, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -haloalkoxy, nitro and cyano,

R.sup.5 is C.sub.1 -C.sub.4 -alkyl, C.sub.2 -C.sub.4 -alkenyl or C.sub.2 -C.sub.4 -alkinyl, cyclohexyl, cyclopentyl, phenyl, pyridyl or thienyl, where the 3 last-mentioned radicals are unsubstituted or substituted by 1 to 3 radicals Z,

R.sup.6 is hydrogen or C.sub.1 -C.sub.4 -alkyl, and

Z is halogen, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -haloalkoxy, C.sub.1 -C.sub.4 -alkylthio, C.sub.1 -C.sub.4 -alkylamino, di-(C.sub.1 -C.sub.4 -alkyl)-amino or nitro.

2. A compound as claimed in claim 1 wherein

R.sup.4 is a C.sub.1 -C.sub.4 -alkoxy radical which is substituted by allyloxy, propargyloxy, (R*).sub.3 Si or (R*).sub.3 SiO, in which the radicals R* independently of one another are methyl, ethyl or phenyl, or by C.sub.1 -C.sub.4 -alkylsulfonyl, C.sub.1 -C.sub.4 -alkylsulfinyl, di-(C.sub.1 -C.sub.4 -alkyl)-phosphinyl, di-(C.sub.1 -C.sub.4 -alkyl) -phosphonyl or di-(C.sub.1 -C.sub.4 -alkyl) -phosphoryl, or is a radical of a 5- or 6-membered cyclic lactone bonded through the carbon in the .alpha.-position relative to the carbonyl group, or R.sup.4 is a radical of the formula

--D.sup.7 --CR.sup.15 R.sup.16 --L

D.sup.7 is O, S or NH,

R.sup.15, R.sup.16 independently of one another are hydrogen or methyl,

L is an acid derivative radical of the formula

--CO--O--R.sup.17

--CO--S--R.sup.18

--CO--O--N.dbd.CR.sup.21 R.sup.22

--CO--N.dbd.CR.sup.21 R.sup.22

--O--CO--R.sup.23 ##STR30## R.sup.17 is hydrogen, C.sub.2 -C.sub.4 -alkenyl or C.sub.2 -C.sub.4 alkinyl, benzyl or phenyl, R.sup.18 is hydrogen, C.sub.1 -C.sub.4 -alkyl, C.sub.2 -C.sub.4 -alkenyl or C.sub.2 -C.sub.4 -alkinyl, benzyl or phenyl,

R.sup.19, R.sup.20 independently of one another are hydrogen, C.sub.1 -C.sub.4 -alkyl, C.sub.2 -C.sub.4 -alkenyl, C.sub.2 -C.sub.4 -alkinyl, cyclohexyl, cyclopentyl, benzyl, phenyl or phenyl substituted by one or more radicals selected from the group consisting of halogen, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -haloalkoxy, nitro and cyano, or together with the nitrogen atom linking them, a heterocyclic 5- or 6-membered ring,

R.sup.24 is C.sub.1 -C.sub.4 -alkyl, which is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, and C.sub.1 -C.sub.4 -alkoxy, or is (C.sub.1 -C.sub.4 -alkoxy)-carbonyl, benzyl, benzoxycarbonyl, phenyl or benzoyl, where the last-mentioned 4 radicals are unsubstituted or substituted by C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, halogen or nitro,

R.sup.25 is hydrogen or C.sub.1 -C.sub.4 -alkyl,

R.sup.26 is hydrogen, C.sub.1 -C.sub.4 -alkyl, C.sub.2 -C.sub.4 -alkenyl or C.sub.2 -C.sub.4 -alkinyl, and

R.sup.27, R.sup.28 independently of one another are hydrogen or C.sub.1 -C.sub.4 -alkyl, or R.sup.4 is a radical of the formula ##STR31## where R.sup.29, R.sup.30, R.sup.31 independently of one another are C.sub.1 -C.sub.4 -alkyl, C.sub.2 -C.sub.4 -alkenyl, C.sub.2 -C.sub.4 -alkinyl or phenyl.

3. A compound as claimed in claim 2, wherein

R.sup.4 is a C.sub.1 -C.sub.4 -alkoxyl radical which is substituted by allyloxy, propargyloxy, (R,).sub.3 Si or (R*).sub.3 SiO, in which the radicals R* independently or one another are methyl, ethyl or phenyl, or by C.sub.1 -C.sub.4 -alkysulfonyl, C.sub.1 -C.sub.4 -alkylsulfinyl, di-(C.sub.1 -C.sub.4 -alkyl)-phosphinyl, di-C.sub.1 -C.sub.4 -alkyl)-phosphonyl or di-(C.sub.1 -C.sub.4 -alkyl)-phosphoryl, or is the radical of a 5- or 6-membered cyclic lactone bonded through the carbon in the .alpha.-position relative to the carbonyl group, or R.sup.4 is a radical of the formula

--D--CR.sup.15 R.sup.16 --L

D.sup.7 is O, S or NH,

R.sup.15, R.sup.16 independently of one another are hydrogen or methyl, L is an acid derivative radical of the formula

--CO--O--R.sup.17 ##STR32## R.sup.17 is hydrogen, C.sub.2 -C.sub.4 -alkenyl or C.sub.2 -C.sub.4 -alkinyl, benzyl or phenyl, R.sup.24 is C.sub.1 -C.sub.4 -alkyl, which is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen and C.sub.1 -C.sub.4 -alkoxy, or is (C.sub.1 -C.sub.4 -alkoxy)-carbonyl, benzyl, benzoxycarbonyl, phenyl or benzoyl, where the last-mentioned 4 radicals are unsubstituted or substituted by C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, halogen or nitro,

R.sup.25 is hydrogen or C.sub.1 -C.sub.4 -alkyl,

R.sup.26 is hydrogen, C.sub.1 -C.sub.4 -alkyl, C.sub.2 -C.sub.4 -alkenyl or C.sub.2 -C.sub.4 -alkinyl, and

R.sup.27, R.sup.28 independently of one another are hydrogen or C.sub.1 -C.sub.4 -alkyl.

4. A compound as claimed in claim 3, wherein

X is O,

R.sup.1, R.sup.2 independently of one another are C.sub.1 -C.sub.4 -alkyl or C.sub.1 -C.sub.4 -alkoxy,

R.sup.3 is isopropyl, tert-butyl or cyclopentyl,

R.sup.4 is a C.sub.1 -C.sub.4 -alkoxy radical which is substituted by allyloxy, propargyloxy, (R*).sub.3 Si or (R*).sub.3 SiO, in which the radicals R* independently of one another are methyl or ethyl, or by C.sub.1 -C.sub.4 -alkylsulfonyl, di-(C.sub.1 -C.sub.4 -alkyl)phosphonyl,

or

is 2-oxo-1-oxolan-3-yl

or

is a radical of the formula

--D.sup.7 --CR.sup.15 R.sup.16 --L

D.sup.7 is O,

R.sup.15 , R.sup.16 independently of one another are hydrogen or methyl

L is an acid derivative radical of the formula

CO--O--R.sup.17 ##STR33## R.sup.17 is hydrogen, allyl, propargyl or benzyl, R.sup.24 is C.sub.1 -C.sub.4 -alkyl,

R.sup.25 is hydrogen or C.sub.1 -C.sub.4 -alkyl

R.sup.26 is hydrogen, C.sub.1 -C.sub.4 -alkyl, C.sub.2 -C.sub.4 -alkenyl or C.sub.2 -C.sub.4 -alkinyl, and

R.sup.27, R.sup.28 independently of one another are hydrogen or methyl.

5. A compound as claimed in claim 2, wherein

R.sup.4 is a radical of the formula ##STR34## where R.sup.29, R.sup.30, R.sup.31 independently of one another are C.sub.1 -C.sub.4 -alkyl, C.sub.2 -C.sub.4 -alkenyl, C.sub.2 -C.sub.4 -alkinyl or phenyl.

6. A compound as claimed in claim 2, wherein R.sup.29, R.sup.30, R.sup.31 independently of one another are C.sub.1 -C.sub.4 -alkyl.

7. A herbicidal or plant growth-regulating composition which comprises an effective amount of a compound of formula (I) as defined in claim 1, and conventional formulation auxiliaries.

8. 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 formula (I) as claimed in claim 1, to the plants, seeds of the plants or the area under cultivation.