Intermediates for the preparation of phenylsulfonylurea herbicides and plant growth regulators

The invention relates to the technical field of herbicides and plant growth regulators, especially herbicides for the selective control of gramineous and other weeds in crops.
It is known that phenylsulfonylureas which are substituted by heterocycles and carry on the phenyl ring an amino group which may be functionalized possess herbicidal and plant growth-regulating properties (EP-A-1 515, U.S. Pat. Nos. 4,892,946; 4,981,509; EP-A-116 518, U.S. Pat. Nos. 4,664,695 and 4,632,695).
It has now been found that, surprisingly, certain phenylsulfonylureas substituted by heterocycles are particularly highly suitable as herbicides or plant growth regulators.
The present invention relates to compounds of the formula (I) or salts thereof ##STR3## in which R.sup.1 is C.sub.1 -C.sub.6 -alkyl, C.sub.2 -C.sub.6 -alkenyl, C.sub.2 -C.sub.6 -alkynyl, the 3 latter radicals independently of one another being unsubstituted or substituted by one or more radicals from the group comprising halogen, C.sub.1 -C.sub.4 -alkoxy, CONH.sub.2, C.sub.1 -C.sub.4 -alkylthio, CN, CHO, (C.sub.1 -C.sub.6 -alkyl)carbonyl, (C.sub.3 -C.sub.6 -cycloalkyl)carbonyl, C.sub.1 -C.sub.4 -alkylsulfonyl, carboxyl, (C.sub.1 -C.sub.4 -alkoxy)carbonyl, (C.sub.2 -C.sub.4 -alkenyloxy)carbonyl, (C.sub.2 -C.sub.4 -alkynyloxy)carbonyl, NO.sub.2, NH.sub.2, mono- and di-(C.sub.1 -C.sub.6)-alkylamino,
R.sup.2 is CO--R.sup.5, COO--R.sup.6, CO--SR.sup.7, CO--NR.sup.8 R.sup.9, CS--NR.sup.10 R.sup.11, CS--OR.sup.12, CS--SR.sup.13, SO.sub.2 R.sup.14, SO.sub.2 NR.sup.15 R.sup.16,
R.sup.3 is COR.sup.17, CO--OR.sup.18, CO--NR.sup.19 R.sup.20, CO--SR.sup.21, CO--O--N.dbd.CR.sup.22 R.sup.23, CSR.sup.24, CSSR.sup.25, CS--OR.sup.26, CS--NR.sup.27 R.sup.28, C(.dbd.NR.sup.29)R.sup.30,
R.sup.4 is H, C.sub.1 -C.sub.6 -alkyl, C.sub.2 -C.sub.6 -alkenyl, C.sub.2 -C.sub.6 -alkynyl, the 3 latter radicals independently of one another being unsubstituted or substituted by one or more halogen radicals,
R.sup.5 is H, C.sub.1 -C.sub.6 -alkyl, C.sub.2 -C.sub.6 -alkenyl, C.sub.2 -C.sub.6 -alkynyl, the three latter radicals independently of one another being unsubstituted or substituted by one or more radicals from the group comprising halogen, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -alkylthio and NR.sup.31 R.sup.32, or unsubstituted or substituted C.sub.3 -C.sub.8 -cycloalkyl, unsubstituted or substituted phenyl, unsubstituted or substituted heteroaryl or phenyl-C.sub.1 -C.sub.4 -alkyl which is unsubstituted or substituted on the phenyl ring,
R.sup.6 is C.sub.1 -C.sub.6 -alkyl, C.sub.2 -C.sub.6 -alkenyl, C.sub.2 -C.sub.6 -alkynyl, the three latter radicals independently of one another being unsubstituted or substituted by one or more radicals from the group comprising halogen, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -alkylthio and NR.sup.31 R.sup.32, or C.sub.3 -C.sub.6 -cycloalkyl which is unsubstituted or substituted by one or more radicals from the group comprising halogen, C.sub.1 -C.sub.4 -alkyl and C.sub.1 -C.sub.4 -alkoxy, or C.sub.3 -C.sub.6 -cycloalkyl-C.sub.1 -C.sub.3 -alkyl,
R.sup.7 is analogous to R.sup.6
R.sup.8 is H, C.sub.1 -C.sub.6 -alkyl, C.sub.2 -C.sub.6 -alkenyl, C.sub.2 -C.sub.6 -alkynyl, the 3 latter radicals independently of one another being unsubstituted or substituted by one or more radicals from the group comprising halogen, or (C.sub.1 -C.sub.6 -alkoxy)carbonyl or C.sub.1 -C.sub.4 -alkoxy,
R.sup.9 is H, C.sub.1 -C.sub.6 -alkyl, C.sub.2 -C.sub.6 -alkenyl, C.sub.2 -C.sub.6 -alkynyl, the 3 latter radicals independently of one another being unsubstituted or substituted by one or more radicals from the group comprising halogen, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -alkylthio and NR.sup.31 R.sup.32, or CO--R.sup.33, CO--OR.sup.34, CO--NR.sup.35 R.sup.36, CS--NR.sup.35 R.sup.36, CS--R.sup.33 or CS--OR.sup.34, or
R.sup.8, R.sup.9 taken together are a divalent radical of the formula --(CH.sub.2).sub.4 --, --(CH.sub.2).sub.5 --, --CH.sub.2 CH.sub.2 --O--CH.sub.2 CH.sub.2 --, --CH.sub.2 CH.sub.2 NHCH.sub.2 CH.sub.2 --, the 4 latter radicals being unsubstituted or substituted by C.sub.1 -C.sub.4 -alkyl,
R.sup.10 is analogous to R.sup.8,
R.sup.11 is analogous to R.sup.9,
R.sup.12 is analogous to R.sup.6,
R.sup.13 is analogous to R.sup.6,
R.sup.14 is C.sub.1 -C.sub.6 -alkyl, C.sub.2 -C.sub.6 -alkenyl, C.sub.2 -C.sub.6 -alkynyl, the three latter radicals independently of one another being unsubstituted or substituted by one or more radicals from the group comprising halogen, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -alkylthio and NR.sup.31 R.sup.32,
R.sup.15 is analogous to R.sup.8,
R.sup.16 is H, C.sub.1 -C.sub.6 -alkyl, C.sub.2 -C.sub.6 -alkenyl, C.sub.2 -C.sub.6 -alkynyl, the 3 latter radicals independently of one another being unsubstituted or substituted by one or more halogen radicals,
R.sup.17 is analogous to R.sup.5,
R.sup.18 is C.sub.1 -C.sub.6 -alkyl, C.sub.2 -C.sub.6 -alkenyl, C.sub.2 -C.sub.6 -alkynyl, the three latter radicals independently of one another being unsubstituted or substituted by one or more radicals from the group comprising halogen, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -alkylthio and NR.sup.31 R.sup.32, or C.sub.3 -C.sub.6 -cycloalkyl which is unsubstituted or substituted by one or more radicals from the group comprising halogen, C.sub.1 -C.sub.4 -alkyl and C.sub.1 -C.sub.4 -alkoxy, or C.sub.3 -C.sub.6 -cycloalkyl-C.sub.1 -C.sub.3 -alkyl or H,
R.sup.19 is analogous to R.sup.8,
R.sup.20 is analogous to R.sup.9,
R.sup.21 is analogous to R.sup.18,
R.sup.22 is H, C.sub.1 -C.sub.4 -alkyl, C.sub.3 -C.sub.5 -alkenyl or C.sub.3 -C.sub.5 -alkynyl,
R.sup.23 is H, C.sub.1 -C.sub.4 -alkyl, C.sub.3 -C.sub.5 -alkenyl or C.sub.3 -C.sub.5 -alkynyl,
R.sup.24 is analogous to R.sup.17,
R.sup.25 is analogous to R.sup.18,
R.sup.26 is analogous to R.sup.18,
R.sup.27 is analogous to R.sup.8,
R.sup.28 is analogous to R.sup.9,
R.sup.29 is H, OH, NH.sub.2, NHR.sup.37, N(R.sup.37).sub.2, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.2 -C.sub.4 -alkenyl or C.sub.2 -C.sub.4 -alkynyl, the 4 latter radicals independently of one another being unsubstituted or substituted by one or more radicals from the group comprising halogen, C.sub.1 -C.sub.3 -alkoxy and C.sub.1 -C.sub.3 -alkylthio,
R.sup.30 is H, C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.6 -alkoxy, C.sub.2 -C.sub.6 -alkenyl, C.sub.2 -C.sub.6 -alkynyl, the four latter radicals independently of one another being unsubstituted or substituted by one or more radicals from the group comprising halogen, C.sub.1 -C.sub.3 -alkoxy and C.sub.1 -C.sub.3 -alkylthio,
each R.sup.31 independently of the others is H, C.sub.1 -C.sub.4 -alkyl, (C.sub.1 -C.sub.4 -alkyl)carbonyl, (C.sub.1 -C.sub.4 -alkoxy)carbonyl or CHO,
each R.sup.32 independently of the others is H or C.sub.1 -C.sub.4 -alkyl,
R.sup.33 is analogous to R.sup.5,
R.sup.34 is analogous to R.sup.6,
R.sup.35, R.sup.36 independently of one another are H, C.sub.1 -C.sub.6 -alkyl, C.sub.2 -C.sub.6 -alkenyl, C.sub.2 -C.sub.6 -alkynyl, the 3 latter radicals independently of one another being unsubstituted or substituted by one or more halogen radicals,
R.sup.37 is C.sub.1 -C.sub.4 -alkyl, C.sub.2 -C.sub.4 -alkenyl or C.sub.2 -C.sub.4 -alkynyl, the three radicals mentioned, independently of one another, being unsubstituted or substituted by one or more radicals from the group comprising halogen, C.sub.1 -C.sub.4 -alkoxy and C.sub.1 -C.sub.4 -alkylthio,
W is O or S,
X and Y independently of one another are hydrogen, halogen, C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.6 -alkoxy or C.sub.1 -C.sub.6 -alkylthio, the three latter radicals being unsubstituted or substituted by one or more radicals from the group comprising halogen, C.sub.1 -C.sub.4 -alkoxy and C.sub.1 -C.sub.4 -alkylthio, or mono- or di-(C.sub.1 -C.sub.4 -alkyl)amino, C.sub.3 -C.sub.6 -cycloalkyl, C.sub.3 -C.sub.5 -alkenyl, C.sub.3 -C.sub.5 -alkenyloxy or C.sub.3 -C.sub.5 -alkynyloxy, and
Z is CH or N.
In the formula (I) and below, each of the radicals alkyl, alkoxy, haloalkyl, haloalkoxy, alkylamino and alkylthio, and the corresponding unsaturated and/or substituted radicals may be straight-chain or branched in the carbon structure. If not indicated specifically, the carbon structures having from 1 to 4 carbon atoms or, in the case of unsaturated groups, having from 2 to 4 carbon atoms are preferred for these radicals. Examples of alkyl radicals, including those in the composite definitions such as alkoxy, haloalkyl etc., are methyl, ethyl, n- or i-propyl, n-, i-, t- or 2-butyl, pentyls, hexyls such as n-hexyl, i-hexyl and 1,3-dimethylbutyl, heptyls such as n-heptyl, 1-methylhexyl and 1,4-dimethylpentyl; alkenyl and alkynyl radicals have the meaning of the unsaturated radicals corresponding, where possible, to the alkyl radicals, examples of alkenyl are allyl, 1-methylprop-2-en-1-yl, 2-methylprop-2-en-1-yl, but-2-en-1-yl, but-3-en-1-yl, 1-methylbut-3-en-1-yl, 1-methylbut-2-en-1-yl and 1-methylbut-2-en-1-yl; examples of alkynyl are propargyl, but-2 -yn-1-yl, but-3-yn-1-yl and 1-methylbut-3-yn-1-yl.
Halogen is fluorine, chlorine, bromine or iodine. Haloalkyl, haloalkenyl and haloalkynyl are respectively alkyl, alkenyl and alkynyl which are partially or completely substituted by halogen, preferably by fluorine, chlorine and/or bromine and in particular by fluorine or chlorine; examples are CF.sub.3, CHF.sub.2, CH.sub.2 F, CF.sub.3 CF.sub.2, CH.sub.2 FCHCl, CCl.sub.3, CHCl.sub.2, CH.sub.2 CH.sub.2 Cl; examples of haloalkoxy are OCF.sub.3, OCHF.sub.2, OCH.sub.2 F, CF.sub.3 CF.sub.2 O, OCH.sub.2 CF.sub.3 and OCH.sub.2 CH.sub.2 Cl. This applies correspondingly to haloalkenyl and other halo-substituted radicals.
Aryl is a mono-, bi- or polycyclic aromatic system, for example phenyl, naphthyl, tetrahydronaphthyl, indenyl, indanyl, pentalenyl, fluorenyl and the like, preferably phenyl; aryloxy preferably comprises the oxy radicals corresponding to the aryl radicals mentioned, in particular phenoxy. Heteroaryl is a mono-, bi- or polycyclic aromatic system in which at least 1 ring contains one or more heteroatoms, for example pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, thienyl, thiazolyl, oxazolyl, furyl, pyrrolyl, pyrazolyl and imidazolyl, but also bicyclic or polycyclic aromatic or araliphatic compounds, e.g. quinolinyl, benzoxazolyl etc.
A substituted aryl, heteroaryl, phenyl, benzyl or substituted bicyclic radical containing aromatic structures is, for example, a substituted radical derived from the unsubstituted parent structure, examples of substituents being one or more radicals, preferably 1, 2 or 3 radicals from the group comprising halogen, alkyl, haloalkyl, alkoxy, haloalkoxy, alkylthio, hydroxyl, amino, nitro, cyano, alkoxycarbonyl, alkylcarbonyl, formyl, carbamoyl, mono- and dialkylaminocarbonyl, mono- and dialkylamino, alkylsulfinyl and alkylsulfonyl and, in the case of radicals containing carbon atoms, those having from 1 to 4 carbon atoms, in particular 1 or 2 carbon atoms, being preferred. Preferred substituents in general are those from the group comprising halogen, e.g. fluorine and 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.4 -haloalkoxy, nitro and cyano. Particularly preferred substituents are methyl, methoxy and chlorine.
Substituted or unsubstituted phenyl is, for example, phenyl which is unsubstituted or substituted once or more than once, preferably up to three times, by identical or different radicals from the group comprising 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 and nitro, e.g. o-, m- and p-tolyl, dimethylphenyls, 2-, 3- and 4-chlorophenyl, 2,3,4-trifluoro- and -trichlorophenyl, 2,4-, 3,5-, 2,5- and 2,3-dichlorophenyl, o-, m- and p-methoxyphenyl.
A heteroaromatic radical preferably has 5 or 6 members and contains 1, 2 or 3 heteroatoms, preferably from the group comprising N, O and S. The radical may be benzofused. Suitable radicals are those such as oxiranyl, pyrrolidinyl, piperidyl, dioxolanyl, pyrazolyl, morpholyl, furyl, tetrahydrofuryl, indolyl, quinolinyl, pyrimidyl, azepinyl, imidazolyl, triazolyl, thienyl and oxazolyl.
The invention also relates to all the stereoisomers encompassed by formula (I), and mixtures thereof. These compounds of the formula (I) contain one or more asymmetric carbon atoms or double bonds which are not indicated specifically in the formula (I). Formula (I) encompasses all the stereoisomers defined by their specific spatial orientation, such as enantiomers, diastereomers, Z- and E-isomers, all of which can be prepared by conventional methods from mixtures of the stereoisomers or else by stereoselective reactions in combination with the use of stereochemically pure starting substances.
The compounds of the formula (I) may form salts in which the hydrogen of the --SO.sub.2 --NH-- group or else another acidic hydrogen atom (e.g. from COOH etc.) is replaced by a cation which is suitable for agriculture. Examples of these salts are metal salts, in particular alkali metal or alkaline earth metal salts, or else ammonium salts or salts with organic amines. The formation of a salt can also take place by the addition of an acid to basic groups such as amino and alkylamino. Suitable acids in this respect are strong inorganic and organic acids, for example HCl, HBr, H.sub.2 SO.sub.4 or HNO.sub.3.
Primarily for reasons of greater herbicidal activity, improved selectivity and/or increased ease of preparation, compounds of the formula (I) or salts thereof of particular interest are those in which
R.sup.1 is C.sub.1-C.sub.4 -alkyl, C.sub.2 -C.sub.4 -alkenyl or C.sub.2 -C.sub.4 -alkynyl, preferably C.sub.1 -C.sub.4 -alkyl, allyl or propargyl, or
R.sup.2 is CO--R.sup.5, COOR.sup.6, CO--NR.sup.8 R.sup.9, CS--NR.sup.10 R.sup.11, SO.sub.2 R.sup.14 or SO.sub.2 NR.sup.15 R.sup.16, or
R.sup.3 is COR.sup.17, COOR.sup.18, CONR.sup.19 R.sup.20 or CO--ON.dbd.CR.sup.22 R.sup.23, preferably COOR.sup.18, or
R.sup.4 is H or C.sub.1 -C.sub.4 -alkyl, preferaby H or methyl, or
R.sup.5 is H, C.sub.1 -C.sub.6 -alkyl which is unsubstituted or substituted by one or more radicals from the group comprising halogen, or by C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -alkylthio or NR.sup.31 R.sup.32, or C.sub.3 -C.sub.6 -cycloalkyl, unsubstituted or substituted phenyl, unsubstituted or substituted benzyl or unsubstituted or substituted heteroaryl, preferably H, C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.4 -haloalkyl, cyclopropyl, cyclopentyl, cyclohexyl, phenyl or heteroaryl, the two latter radicals being unsubstituted or substituted by one or more radicals from the group comprising C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy and halogen, or
R.sup.6 is C.sub.1 -C.sub.6 -alkyl, C.sub.2 -C.sub.6 -alkenyl, C.sub.2 -C.sub.6 -alkynyl, C.sub.1 -C.sub.6 -haloalkyl or C.sub.3 -C.sub.6 -cycloalkyl, preferably C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -haloalkyl, allyl, propargyl or C.sub.3 -C.sub.6 -cycloalkyl, or
R.sup.7 is C.sub.1 -C.sub.4 -alkyl,
R.sup.8 is hydrogen, C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.4 -haloalkyl. C.sub.1 -C.sub.4 -alkoxy or (C.sub.1 -C.sub.4 -alkoxy)carbonyl,
R.sup.9 is hydrogen, C.sub.1 -C.sub.6 -alkyl which is unsubstituted or substituted by one or more radicals from the group comprising halogen, C.sub.1 -C.sub.4 -alkoxy and NR.sup.31 R.sup.32, or CO--R.sup.33, CO--OR.sup.34 or CO--NR.sup.35 R.sup.36, or
R.sup.8 and R.sup.9 taken together are a divalent radical of the formula --(CH.sub.2).sub.4 --, --(CH.sub.2).sub.5 -- or --CH.sub.2 CH.sub.2 --O--CH.sub.2 CH.sub.2 --, or
R.sup.14 is C.sub.1 -C.sub.6 -alkyl or C.sub.1 -C.sub.6 -haloalkyl, preferably C.sub.1 -C.sub.4 -alkyl or C.sub.1 -C.sub.4 -haloalkyl, or
R.sup.15, R.sup.16 independently of one another are hydrogen or C.sub.1 -C.sub.4 -alkyl, or
R.sup.17 is hydrogen or C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -haloalkyl, C.sub.3 -C.sub.6 -cycloalkyl, phenyl or heteroaryl, the two latter radicals being unsubstituted or substituted, or
R.sup.18 is hydrogen, C.sub.1 -C.sub.4 -alkyl, C.sub.2 -C.sub.6 -alkenyl or C.sub.2 -C.sub.6 -alkynyl, the 3 latter radicals being unsubstituted or substituted by one or more radicals from the group comprising halogen, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -alkylthio and NR.sup.31 R.sup.32, or C.sub.3 -C.sub.6 -cycloalkyl or C.sub.3 -C.sub.6 -cycloalkyl-C.sub.1 -C.sub.3 -alkyl, or
R.sup.22 is hydrogen or C.sub.1 -C.sub.2 -alkyl, or
R.sup.23 is hydrogen or C.sub.1 -C.sub.2 -alkyl, or
R.sup.29 is hydrogen, hydroxyl, amino, NHCH.sub.3, N(CH.sub.3).sub.2, C.sub.1 -C.sub.4 -alkyl or C.sub.1 -C.sub.4 -alkoxy,
R.sup.30 is hydrogen or C.sub.1 -C.sub.4 -alkyl, or
each R.sup.31 independently of the others is H or C.sub.1 -C.sub.4 -alkyl, or
each R.sup.32 independently of the others is H or C.sub.1 -C.sub.4 -alkyl, or
R.sup.33 is hydrogen, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -haloalkyl, C.sub.3 -C.sub.6 -cycloalkyl or phenyl which is unsubstituted or substituted by one or more radicals from the group comprising halogen, C.sub.1 -C.sub.4 -alkyl and C.sub.1 -C.sub.4 -alkoxy, or
R.sup.34 is C.sub.1 -C.sub.4 -alkyl, allyl, propargyl or cycloalkyl, or
R.sup.35 is hydrogen or C.sub.1 -C.sub.4 -alkyl, or
R.sup.36 is hydrogen or C.sub.1 -C.sub.4 -alkyl, or
X is 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 -alkylthio, halogen or mono- or di-(C.sub.1 -C.sub.2 -alkyl)amino, preferably methyl, ethyl, methoxy, ethoxy, methylthio, ethylthio, chlorine, NHCH.sub.3 or N(CH.sub.3).sub.2, or
Y is C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkyl or C.sub.1 -C.sub.4 -alkylthio, preferably methyl, ethyl, methoxy or ethoxy,
or preferably those compounds of the formula (I) or salts thereof in which two or more of the particular or preferred definitions mentioned above for the radicals R.sup.1 to R.sup.36 in formula (I) are present in combination.
Preferred compounds of the formula (I) or salts thereof are those in which
R.sup.1 is methyl, ethyl, n-propyl, i-propyl or allyl,
R.sup.2 is CO--R.sup.5, COOR.sup.6, CO--NR.sup.8 R.sup.9, CS--NR.sup.10 R.sup.11, SO.sub.2 R.sup.14 or SO.sub.2 NR.sup.15 R.sup.16,
R.sup.5 is H, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.2 -haloalkyl, cyclopropyl, phenyl, benzyl or heteroaryl having 5 or 6 ring atoms, the 3 latter radicals being unsubstituted or substituted by one or more halogen atoms,
R.sup.6 is C.sub.1 -C.sub.4 -alkyl, allyl, propargyl or cyclopropyl,
R.sup.8 is H, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -haloalkyl or (C.sub.1 -C.sub.4 -alkoxy)carbonyl,
R.sup.9 is H or C.sub.1 -C.sub.4 -alkyl,
R.sup.10 is H or C.sub.1 -C.sub.4 -alkyl,
R.sup.11 is H or C.sub.1 -C.sub.4 -alkyl,
R.sup.14 is C.sub.1 -C.sub.4 -alkyl,
R.sup.15 is H or C.sub.1 -C.sub.4 -alkyl and
R.sup.16 is H or C.sub.1 -C.sub.4 -alkyl.
R.sup.5 is particularly preferably H, CH.sub.3, C.sub.2 H.sub.5, n- or i-C.sub.3 H.sub.7, n-, i-, t- or 2-butyl, n-pentyl, CF.sub.3, CH.sub.2 Cl, CHCl.sub.2, CCl.sub.3, CH.sub.2 Br, CH.sub.2 CCl.sub.3, cyclopropyl, phenyl, thienyl, furyl or pyridyl, in which case the 4 latter radicals may be substituted by from 1 to 3 halogen atoms.
The present invention also relates to processes for the preparation of the compounds of the formula (I) according to the invention or salts thereof, which comprises
a) reacting a compound of the formula (II) ##STR4## with a heterocyclic carbamate of the formula (III) ##STR5## in which R* is unsubstituted or substituted phenyl or C.sub.1 -C.sub.4 -alkyl, or
b) reacting a sulfonyl isocyanate of the formula (IV) ##STR6## with an amino heterocycle of the formula (V) ##STR7## or c) reacting a compound of the formula (II) with a (thio)isocyanate of the formula (X) ##STR8## in the presence of a base, the radicals R.sup.1 to R.sup.4, W, X, Y and Z in the above formulae (II) to (V) and (X) being as defined in formula (I) and, in the case of variants a) and b), the compounds initially obtained being those of the formula (I) in which W=O.
The reaction of the compounds of the formulae (II) and (III) is preferably carried out base-catalyzed in an inert organic solvent, for example dichloromethane, acetonitrile, dioxane or THF, at temperatures between 0.degree. C., preferably 20.degree. C., and the boiling point of the solvent. Examples of the base used are organic amine bases, such as 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU), especially when R*=(substituted) phenyl (cf. EP-A-44 807), or trimethylaluminum or triethylaluminum, the latter especially when R*=alkyl (cf. EP-A-166 516).
The sulfonamides (II) and the sulfonyl isocyanates (IV) are new compounds. They and their preparation are also subjects of the invention.
The compounds of the formula (II) are obtained, for example, starting from compounds of the formula (VI) ##STR9## in which R.sup.1, R.sup.2 and R.sup.3 are as defined in formula (I), by reaction with a strong acid (cf. in this respect WO 89/10921).
Examples of suitable strong acids are mineral acids, such as H.sub.2 SO.sub.4 or HCl, or strong organic acids such as trifluoroacetic acid. The elimination of the tert-butyl protective group is carried out, for example, at temperatures from -20.degree. C. to the respective reflux temperature of the reaction mixture, preferably at 0.degree. C. The reaction can be carried out without solvent or else in an inert solvent, for example dichloromethane or trichloromethane.
The compounds of the formula (VI) are obtained, for example, from the compounds of the formula (VI')-which corresponds to the formula (VI) but in which R.sup.2 =H-by reaction with suitable electrophiles such as acid chlorides, acid anhydrides, isocyanates, thioisocyanates, sulfonyl chlorides or amidosulfonyl chlorides (cf. in this respect: A. L. J. Beckniter in J. Zabicky, "The Chemistry of Amides", pp. 73-185, Interscience, New York, 1970, E. J. Corey et al., Tetrahedron Lett. 1978, 1051; H. J. Saunders, R. J. Slocombe, Chem. Rev. 43, 203 (1948); S. Ozaki, Chem. Rev. 72, 457, 469 (1972); G. zolB, Arzneim.-Forsch. 33, 2 (1983); Houben-Weyl-Hagemann, "Methoden der organischen Chemie [Methods of Organic Chemistry]", 4th edition, vol. E4, p. 485 ff., Thieme verlag Stuttgart, 1983; J. Golinsky, M. Mahosza, Synthesis 1978, 823; Houben-Weyl-Muller, "Methoden der organischen Ghemie", 4th edition, vol. IX, pp. 338-400 and 605-622, Thieme Verlag Stuttgart, 1955; Houben-Weyl-Klarmann, "Methoden der organischen Chemie", 4th edition, vol. E 11/2, pp. 1020-22, Thieme Verlag Stuttgart, 1985; S. Krishnamurthey, Tetrahedron Lett. 23, 3315 (1982)).
The N-monosubstituted aminobenzene derivatives, for example N-alkylaminobenzene derivatives, which are required for this purpose, of the formula (VI') (see formula (VI), R.sup.2 =H) are obtained by monoalkylation of the anilines of the formula (VI") (=formula (VI), R.sup.1 =H and R.sup.2 =H) by standard methods. For example, the N-acylation of the anilines of the formula (VI") with carboxylic acid chlorides or carboxylic acid anhydrides gives the corresponding N-acyl-anilines. The subsequent reduction of the acylamino group to the analogous N-monosubstituted amino group, e.g. alkylamino group (see above) using suitable reducing agents, for example borane/dimethyl sulfide complex, gives the aniline derivatives of the formula (VI') (=formula (VI), R.sup.2 =H) in very good yields; see S. Krishnamurthey, Tetrahedron Leet. 23, 3315 (1982).
The aniline derivatives mentioned of the formula (VI') (=formula (VI), R.sup.1 and R.sup.2 =H) are obtained by methods known from the literature, by reduction of the nitro group in compounds (VII), for example by hydrogenation with hydrogen in the presence of a suitable catalyst, as Pd/C or Raney nickel, or by reduction with iron in a medium acidified with acetic acid. (cf. in this respect: H. Berrie, G. T. Neuhold, F. S. Spring, J. Chem, Soc. 1952, 2042; M. Freifelder, "Catalytic Hydrogenation in Organic Synthesis: Procedures and Commentary", J. Wiley and Sons, New York (1978) chapter 5).
The aromatic sulfonamides of the formula (VII) can be obtained from the sulfonic acids of the formula (VIII). ##STR10##
The sulfonic acid group in compounds (VIII) is first converted to the sulfonyl chlorides, for example by standard methods such as the reaction of phosphorus oxychloride or thionyl chloride with potassium salts of the corresponding sulfonic acids in inert solvents such as acetonitrile and/or sulfolane, or without solvent, by heating at reflux (cf. Houben-Weyl-Klamann, "Methoden der organischen Chemie", 4th edition, vol. E XI/2, pp. 1067-1073, Thieme Verlag Stuttgart, 1985).
The formation of sulfonamide from the sulfonyl chlorides using tert-butylamine in ethanol gives the compounds (VII) in good yields (cf. analogous reactions in WO 89/10921).
The sulfonic acids of the formula (VIII) can be prepared from 2-methyl-5-nitrobenzenesulfonic acid, which is available commercially.
The substituent R.sup.3 is introduced by oxidation of the methyl group of 2-methyl-5-nitrobenzenesulfonic acid using standard methods, such as the reaction with potassium permanganate to give the carboxyl group, followed if desired by derivatization, for example esterification or amidation (cf. in this respect: Houben-Weyl-Falbe: "Methoden der organischen Chemie", 4th edition, vol. E V/1, Thieme Verlag Stuttgart, 1985, pp. 199-202).
A wide variation in the radical R.sup.3 can be obtained using a range of standard reactions:
Carboxylic acid amides are obtainable by reacting acid anhydrides or acid chlorides with amines (cf. in this respect: A. L. J. Beckwith in J. Zabicky, "The Chemistry of Amides", pp. 73-185, Interscience, New York 1970).
Thiocarboxylic acid S-esters can be prepared from carboxylic acids and thiols with carbonyl activation, for example using diphenylphosphinyl chloride (cf. in this respect: D. Scholz, D. Eigner, Monatsh. Chemie 110, 759 (1979), S. Yamada et al., J. Org. Chem. 39, 3302 (1974)).
Thiocarboxylic acid O-esters can be prepared by reacting carboxylic acid esters with suitable reagents, for example P.sub.4 S.sub.10 (cf. in this respect: S. O. Lauresson et al., Bull. Soc. Chim. Belg. 87, 293 (1978); T. Nishiwak et al., Chem. Lett. 1980, 401).
Thiocarboxylic acid amides are obtained from carboxylic acid amides by "sulfurization", for example with phosphorus pentasulfide (Houben-Weyl-Falbe, "Methoden der organischen Chemie", 4th edition, vol. E 5/2, pp. 1242-1247 (and literature cited therein), Thieme Verlag Stuttgart, 1985).
Aldehydes can be synthesized from carboxylic acids or esters using a range of reducing agents (Houben-Weyl-Falbe, "Methoden der organischen Chemie", 4th edition, vol. E 3, p. 418 ff., Thieme Verlag Stuttgart, 1983).
Functionalized aldehyde derivatives, for example oximes, oxime ethers, hydrazones etc., can be obtained from the aldehydes by condensation with the corresponding amines (cf. in this respect: Houben-Weyl-Muller, "Methoden der organischen Chemie", 4th edition, vol. 7/1, pp. 453-474, Thieme Verlag Stuttgart, 1954).
N-Alkoxy-carboxylic acid imide esters can be prepared from hydroxamic acid bromide derivatives and alcoholates (E. C. Tayler, F. Kienzle, J. Org. Chem. 36, 233 (1971).
Carboxylic acid imide esters can be obtained from carboxylic acid chloride imides and corresponding alcoholates (cf. in this respect: H. Bohme, O. Muller, Chem. Ber. 98, 1450 (1965); G. Bock, Chem. Ber. 100, 2870 (1967).
O-Acyl oximes can be prepared, for example, by reacting carboxylic acid anhydrides with ketoximes (cf. in this respect: S. Bittner, Y. Knobler, M. Frankel, Tetrahedron Lett. 1965, 95).
Hydroxamic acid amides can be obtained by reacting hydroxamic acid chloride derivatives with amines (cf. in this respect: Houben-Weyl-Muller, "Methoden der organischen Chemie", 4th edition, vol. 10/4, p. 209 ff., Thieme Verlag Stuttgart, 1968).
Alternatively, the sulfonamides of the formula (II) in which R.sup.1 and R.sup.2 are not H can be obtained by aminolysis of the corresponding sulfonyl chlorides of the formula (IXb) ##STR11## which in turn are readily obtainable from the sulfonic acids (IXa) by the standard methods mentioned (see abovementioned reactions of (VIII) to (VII)).
The compounds (IXa) can in turn be obtained from the nitrobenzenesulfonic acid (VIII) by the sequence of reactions
(1) reduction by analogy with reduction of (VII),
(2) N-alkylation and
(3) N-acylation,
the latter being as described in the preparation of (VI).
The carbamates of the formula (III) which are required for the reaction of compounds (II) by variant a) are known from the literature or can be prepared by analogy with known processes (cf. EP-A-70 804 or U.S. Pat. No. 4,480,101).
The compounds of the formulae (IV) and (V) which can be employed for the process variants b) can also be prepared from the abovementioned compounds of the formulae (III) and (VIII) and their precursors by, or by analogy with, methods which are known in general terms.
The phenylsulfonyl isocyanates of the formula (IV) can be prepared for example, by analogy with the processes from EP-A-184 385 starting from compounds of the formula (II) and using, for example, phosgene.
The reaction of the compounds (IV) with the amino heterocycles of the formula (V) is preferably carried out in inert aprotic solvents, for example dioxane, acetonitrile or tetrahydrofuran, at temperatures between 0.degree. C. and the boiling temperature of the solvent.
The (thio) isocyanates of the formula (X) can be prepared by methods known from the literature (cf. EP-A-232 067, EP-A-166 516).
The reaction of compounds of the formula (X) with sulfonamides of the formula (II) is carried out at temperatures of between -10.degree. C. and +10.degree. C., preferably between +20.degree. and +80.degree. C., in an inert aprotic solvent, for example acetone or acetonitrile, in the presence of a suitable base such as triethylamine or potassium carbonate.
The salts of the compounds of the formula (I) are preferably prepared in inert solvents such as water, methanol, acetone, dichloromethane, tetrahydrofuran, toluene or heptane, at temperatures from 0.degree. to 100.degree. C. Examples of bases suitable for the preparation of the salts according to the invention are alkali metal carbonates, such as potassium carbonate, alkali metal and alkaline earth metal hydroxides, ammonia or a suitable amine base, such as triethylamine or ethanolamine. Examples of acids suitable for salt formation are HCl, HBr, H.sub.2 SO.sub.4 or HNO.sub.3.
The inert solvents referred to in the abovementioned process variants are in each case solvents which are inert under the respective reaction conditions, but which are not necessarily inert under any reaction conditions.
The compounds of the formula (I) according to the invention or their salts have an excellent herbicidal activity against a broad range of economically important monocotyledon and dicotyledon harmful plants. The active substances 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 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 the mention intending 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 Convolvulus, Cirsium, Rumex and Artemisia in the case of the perennial weeds.
The active substances according to the invention likewise 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, eventually, after three to four weeks have elapsed, they die completely.
If the active substances are applied post-emergence on the green parts of the plants, growth likewise stops drastically a very short time after the treatment and the weed plants remain at the growth stage of the point in 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 point in time and in a sustained manner.
Even though the compounds according to the invention have an excellent herbicidal activity against monocotyledon and dicotyledon weeds, crop plants of economically important crops, such as, for example, wheat, barley, rye, rice, maize, sugar beet, cotton and soya, are damaged not at all, or only to a negligible extent. For these reasons, the present compounds are highly suitable for selectively controlling unwanted plant growth in agricultural crop plants.
In addition, the substances according to the invention exhibit outstanding growth-regulatory properties in crop plants. They intervene to regulate the plant metabolism and can therefore be employed so as to have a specific influence on substances contained in plants, and for facilitating harvesting, for example by initiating desiccation and growth compression. Furthermore, they are also suitable for the general control and inhibition of unwanted vegetative growth, without killing off the plants in the process. Inhibition of vegetative growth plays an important role in many monocotyledon and dicotyledon crops, since it can reduce or completely prevent lodging.
The compounds according to the invention can be used in the form of wettable powders, emulsifiable concentrates, sprayable solutions, dusting agents or granules in the conventional formulations. The invention therefore also relates to herbicidal and plant growth-regulating agents comprising compounds of the formula (I) or salts thereof.
The compounds of the formula (I) or salts thereof can be formulated in a variety of ways, as predetermined by the biological and/or chemicophysical parameters. The following possibilities are therefore suitable for formulation: 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), dispersions on an oil or water base, oil-miscible solutions, capsule suspensions (CS), dusting agents (DP) seed-dressing agents, granules for scattering and soil application, granules (GR) in the form of microgranules, sprayable granules, coated 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 Technologie [Chemical Technology]", Volume 7, C. Hauser Verlag Munich, 4th Ed., 1986; Wade van Valkenburg, "Pesticide Formulations", Mercel Dekker N.Y., 1973; K. Martens, "Spray Drying" Handbook, 3rd Ed. 1979, G. Goodwin Ltd. London.
The formulation auxiliaries required, such as inert materials, surfactants, solvents and other additives, are likewise known and are described, for example, in: Watkins, "Handbook of Insecticide Dust Diluent and Carriers", 2nd Ed., Darland Books, Caldwell N.J., H. v. Olphen, "Introduction to Clay Colloid Chemistry", 2nd Ed., J. Wiley & 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-Kuchler, "Chemische Technologie [Chemical Technology]", Volume 7, C. Hauser Verlag Munich, 4th Ed. 1986.
Combinations with other pesticidally active substances, such as insecticides, acaricides, herbicides, fungicides, safeners, fertilizers and/or growth regulators may also be prepared on the basis of these formulations, for example in the form of a ready-to-use formulation or as a tank mix.
Wettable powders are preparations which are uniformly dispersible in water and which, besides the active substance, also contain surfactants of ionic and/or nonionic type (wetting agents, dispersants), for example polyethoxylated alkylphenols, polyethoxylated fatty alcohols, polyethoxylated fatty amines, fatty alcohol polyglycol ether sulfates, alkanesulfonates, alkylbenzenesulfonates, sodium ligninsulfonate, sodium 2,2'-dinaphthylmethane-6,6'-disulfonate, sodium dibutylnaphthalenesulfonate, or alternatively sodium oleoylmethyltaurinate, in addition to a diluent or inert substance. The wettable powders are prepared by finely grinding the herbicidal active substances, for example, in conventional apparatus such as hammer mills, blower mills and air-jet mills, and mixing them simultaneously or subsequently with the formulation auxiliaries.
Emulsifiable concentrates are prepared by dissolving the active substance in an organic solvent, for example butanol, cyclohexanone, dimethylformamide, xylene and also higher-boiling aromatic compounds or hydrocarbons or mixtures of the organic solvents, with the addition of one or more surfactants of ionic and/or nonionic type (emulsifiers). Examples of emulsifiers which can be used are: calcium salts of an alkylarylsulfonic acid 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, such as sorbitan fatty acid esters or polyoxyethylene sorbitan esters, such as polyoxyethylene sorbitan fatty esters.
Dusting agents are obtained by grinding the active substance with finely divided solid substances, for example talc or natural clays, such as kaolin, bentonite, pyrophyllite or diatomaceous earth.
Suspension concentrates may be based on water or oil. They can be prepared by, for example, wet grinding using conventional bead mills with the possible addition of surfactants as already mentioned, for example, above for the other types of formulation.
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, surfactants, for example as already listed above for the other types of formulation.
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.
Water-dispersible granules are generally prepared by conventional methods such as spray-drying, fluidized-bed granulation, plate granulation, mixing using high-speed mixers and extrusion without solid inert material.
The agrochemical formulations generally contain from 0.1 to 99% by weight and in particular from 0.1 to 95% by weight of active substance of the formula (I) or salts thereof.
The concentration of active substance in wettable powders is, for example, about 10 to 90% by weight; the remainder to 100% by weight is composed of conventional formulation components. In the case of emulsifiable concentrates, the concentration of active substance can be about 1 to 90, preferably 5 to 80% by weight. Formulations in the form of dusts usually contain 1 to 30, preferably 5 to 20% by weight of active substance, sprayable solutions about 0.05 to 80, preferably 2 to 50% by weight. In the case of water-dispersible granules, the active substance content depends partly on whether the active compound is liquid or solid and on which granulation auxiliaries, fillers etc. are used. In the case of the water-dispersible granules, the content of active substance is, for example, between 1 and 95% by weight and preferably between 10 and 80% by weight.
In addition, the active substance formulations mentioned contain, if appropriate, the adhesives, wetting agents, dispersants, emulsifiers, penetrants, preservatives, frost protectors and solvents, fillers, carriers and colorants, antifoams, evaporation inhibitors and agents influencing the pH and the visocity which are conventional in each case.
Combination partners which can be employed for the active substances according to the invention in mixed formulations or as a tank mix are, for example, known active substances as described in, for example, Weed Research 26, 441-445 (1986), or "The Pesticide Manual", 9th edition, The British Crop Protection Council, 1990/91, Bracknell, England, and the literature quoted therein. Examples of herbicides known from the literature which can be combined with the compounds of the formula (I) are the following active substances (note: the compounds are either given by their common name in accordance with the International Organization for Standardization (ISO) or by the chemical name, together if appropriate with a common 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 its methyl ester; 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; pirifenop-butyl; chlorbromuron; chlorbufam; chlorfenac; chlorflurecol-methyl; chloridazon; chlorimuron ethyl; chlornitrofen; chlorotoluron; chloroxuron; chlorpropham; chlorsulfuron; chlorthaldimethyl; chlorthiamid; cinmethylin; cinosulfuron; clethodim; clomazone; clomeprop; cloproxydim; clopyralid; cyanazine; cycloate; cycloxydim; cycluron; cyperquat; cyprazine; cyprazole; 2,4-DB; dalapon; desmediphan; desmetryn; di-allate; dicamba; dichlobenil; dichlorprop; diclofop-methyl; diethatyl; difenoxuron; difenzoquat; diflufenican; dimefuron; dimethachlor; dimethametryn; dimethazone; clomazon; dimethipin; dimetrasulfuron, cinosulfuron; dinitramine; dinoseb; dinoterb; diphenamid; dipropetryn; 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; ethafluralin; ethametsulfuron-methyl; ethidimuron; ethiozin; 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]pyrimidin-2-sulfonamide; flumeturon; flumipropyn; fluorodifen; fluoroglycofen-ethyl; fluridone; flurochloridone; fluroxypyr; flurtamone; fomesafen; fosamine; furyloxyfen; glufosinate; glyphosate; halosaten; haloxyfop and its ester derivatives; hexazinone; Hw 52, i.e. N-(2,3-dichlorophenyl)-4-(ethoxymethoxy)benzamide; imazamethabenzmethyl; imazapyr; imazaquin; imazethamethapyr; imazethapyr; imazosulfuron; ioxynil; isocarbamid; isopropalin; isoproturon; isouron; isoxaben; isoxapyrifop; karbutilate; lactofen; lenacil; linuron; MCPA; MCPB; mecoprop; mefenacet; mefluidid; metamitron; 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; nitralin; nitrofen; nitrofluorfen; norflurazon; orbencarb; oryzalin; oxadiazon; oxyfluorfen; paraquat; pebulate; pendimethalin; perfluidone; 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; quinclorac; quinmerac; quinofop and its ester derivatives, quizalofop and its ester derivatives; quizalofopethyl; 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-benzoxazin-6-yl]-4,5,6,7-tetrahydro-1H-isoindole-1,3(3H)-dione; secbumeton; sethoxydim; siduron; simazine; simetryn; SN 106279, i.e. 2-[[7-[2-chloro-4-(trifluoromethyl)phenoxy]-2-naphthyl]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; thiazafluoron; thifensulfuron-methyl; thiobencarb; tiocarbazil; tralkoxydim; tri-allate; triasulfuron; triazofenamide; tribenuronmethyl; triclopyr; tridiphane; trietazine; trifluralin; trimeturon; vernolate; WL 110547, i.e. 5-phenoxy-1-[3-(trifluoromethyl)phenyl]-1 H-tetrazole.
For use, the formulations, present in commercially available form, are diluted, if appropriate, in a customary manner, for example using water in the case of wettable powders, emulsifiable concentrates, dispersions and water-dispersible granules and then applied to plants, plant parts or agriculturally or industrially utilized soil, on which the plants are located, or in which they grow or are present as seed. Preparations in the form of dusts or granules for soil application and scattering, and also sprayable solutions, are usually not further diluted with other inert substances before use.
The application rate required for the compounds of the formula I varies with the external conditions, such as, inter alia, temperature, humidity, and the nature of the herbicide used. It can vary within wide limits, for example between 0.001 and 10.0 kg/ha or more of active substance; preferably, however, it is between 0.005 and 5 kg/ha.

A) Chemical Examples
a) 2-Carboxy-nitrobenzenesulfonic acid 400.0 g (2.53 mol) of potassium permanganate are added in portions at 80.degree. C. over a period of 2 h to a solution of 106.0 g (0.40 mol) of 2-methyl-5-nitrobenzenesulfonic acid and 80.0 g (0.58 mol) of potassium carbonate in 1300 ml of water. The reaction temperature is maintained at between 80.degree. and 95.degree. C. After stirring for a further 4 h, the solid formed is filtered off. The filtrate is acidified with concentrated hydrochloric acid (pH=1). The colorless 2-carboxy-5-nitrobenzenesulfonic acid which has precipitated is filtered off with suction through a Buchner funnel and dried at about 50.degree. C./100 torr (82.0 g; 83.7% of theory). Melting point: >300.degree. C.
b) 2-Methoxycarboxy-5-nitrobenzenesulfonic acid
A suspension of 190.0 g (0.77 mol) of 2-carboxy-5-nitrobenzenesulfonic acid, 10 ml of DMF and 250 ml (3.43 mol) of thionyl chloride is heated at boiling for 3 h. After separating off the insoluble constituents by filtration, the filtrate is concentrated. 200 ml (4.94 mol) of methanol are added to the residue which results. When addition is complete the reaction mixture is cooled to 0.degree. C. The solid which precipitates is filtered off and dried. 70.9 g (35.3% of theory) of colorless, crystalline 2-methoxycarbonyl-5-nitrobenzenesulfonic acid (m.p.: 92.degree.-94.degree. C.) are thus obtained. By distilling off the volatile components from the mother liquor, a second fraction (62.5 g, 31.1% of theory) is obtained.
c) 2-Methoxycarbonyl-5-nitrobenzenesulfonyl chloride
A solution of 17.3 g (0.27 mol) of potassium hydroxide (88% strength) and 100 ml of methanol is added carefully with vigorous stirring to a solution of 70.9 g (0.27 mol) of 2-methoxycarbonyl-5-nitrobenzenesulfonic acid in 300 ml of methanol. The mixture is cooled to 0.degree. C. and the salt which is precipitated is filtered off, dried and then suspended in 150 ml of sulfolane, 150 ml of acetonitrile and 10 ml of dimethylformamide. After the dropwise addition of 100 ml (1.07 mol) of phosphorus oxychloride, the mixture is heated at boiling for 2.5 h. The reaction mixture is then poured into ice-water. The 2-methoxycarbonyl-5-nitrobenzenesulfonyl chloride (60.1 g, 70% of theory) which has precipitated is filtered off with suction through a Buchner funnel and freed from traces of solvent under reduced pressure. Melting point: 86.degree.-88.degree. C.
d) N-tert-Butyl-2-methoxycarbonyl-5-nitrobenzenesulfonamide
50 ml (0.48 mol) of tert-butylamine are slowly added dropwise at 0.degree. C. to a solution of 34.4 g (0.12 mol) of 2-methoxycarbonyl-5-nitrobenzenesulfonyl chloride in 200 ml of ethyl acetate and 250 ml of ethanol. The reaction solution is then stirred for a further 10 min at room temperature. After the addition of 500 ml of water, a colorless solid crystallizes out. It is filtered off and dried to give 28.1 g (89% of theory) of N-tert-butyl-2-methoxycarbonyl-5-nitrobenzenesulfonyl chloride. m.p.: 121.degree.-124.degree. C.
e) N-tert-Butyl-5-amino-2-methoxycarbonylbenzenesulfonamide
25.08 g (0.079 mol) of N-tert-butyl-2-methoxycarbonyl-5-nitrobenzenesulfonamide are dissolved in 1000 ml of MeOH. 0.50 g of Pd-C (10%) is added and the mixture is shaken under a hydrogen atmosphere (1 atm) until the uptake of hydrogen has finished. The catalyst is separated off and the solvent is removed by distillation. The residue is induced to crystallize by stirring with a little ethyl acetate. The resulting N-tert-butyl-5-amino-2-methoxycarbonylbenzenesulfonamide (18.3 g; 80.9% of theory) melts at 193.degree. C.
f) N-tert-Butyl-5-formylamino-2-methoxycarbonylbenzenesulfonamide
6.5 ml of formic acid are carefully added at 0.degree. C. to 13 ml of acetic anhydride. The mixture is subsequently heated at 50.degree.-60.degree. C. for 2 h. A solution of 16.0 g (0.056 mol) of N-tert-butyl-5-amino-2-methoxycarbonylbenzenesulfonamide in 50 ml of DMF is then added dropwise at 0.degree. C. The cooling bath is removed and the mixture is stirred for a further 4 h at room temperature. The reaction mixture is then taken up in 800 ml of ethyl acetate and washed with three times 150 ml of water. The organic phase is dried over magnesium sulfate, the solvent is distilled off, and the residue is recrystallized from ethyl acetate/n-heptane. The product is N-tert-butyl-5-formylamino-2-methoxycarbonylbenzenesulfonamide (14.23 g, 82% of theory) which melts at 113.degree.-114.degree. C.
g) N-tert-Butyl-2-methoxycarbonyl-5-methylaminobenzenesulfonamide
9.92 g (0.032 mol) of N-tert-butyl-5-formylamino-2-methoxycarbonylbenzenesulfonamide are dissolved in 50 ml of CHCl.sub.3, and then 5 ml (0.053 mol) of boranedimethyl sulfide complex are added at 0.degree. C. After 1 h at 0.degree. C. and 3 h at room temperature the reaction mixture is cooled to 0.degree. C. 30 ml of methanol are added and the mixture is washed with water. The organic phase is dried over magnesium sulfate, the solvent is removed by distillation, and 9.23 g (98% of theory) of N-tert-butyl-2-methoxycarbonyl-5-methylaminobenzenesulfonamide are obtained. m.p.: 120.degree.-124.degree. C.
h) N-tert-Butyl-5-[N-(ethoxycarbonylaminothiocarbonyl)methylamino]-2-methoxycarbonylbenzenesulfonamide
1.20 g (4.0 mmol) of N-tert-butyl-2-methoxycarbonyl-5-methylaminobenzenesulfonamide is dissolved in 5 ml of anhydrous DMF, and 0.60 g (4.3 mmol) of 95% strength ethoxycarbonyl isothiocyanate is added. After 3 h at room temperature the mixture is taken up in ethyl acetate and washed with 1N hydrochloric acid and water. The organic phase is dried over magnesium sulfate and the solvent is removed by distillation. The residue is taken up in a little ethyl acetate and precipitated with heptane at -25.degree. C. The precipitate is filtered off with suction and dried to give 1.29 g (75% of theory) of colorless N-tert-butyl-5-[N-(ethoxycarbonylaminothiocarbonyl)methylamino]-2-methoxycarbonylbenzenesulfonamide. m.p.: 110.degree. C.
i) 5-[N-(Ethoxycarbonylaminothiocarbonyl)methylamino]-2-methoxycarbonylbenzenesulfonamide
1.05 g (2.4 mmol) of N-tert-butyl-5-[N-(ethoxycarbonylaminothiocarbonyl)methylamino]-2-methoxycarbonylbenzenesulfonamide is stirred for 18 h in 15 ml of trifluoroacetic acid at room temperature. Volatile components are then removed by distillation at 12 torr/50.degree. C. The residue is suspended in toluene. The suspension is again concentrated at 12 torr/50.degree. C. to give a highly viscous residue (0.85 g, 93% of theory) which is reacted directly without further purification to give the corresponding sulfonylurea (cf. Example j).
j) N-[(4,6-Dimethoxypyrimidin-2-yl)aminocarbonyl]-5-[N-(ethoxycarbonylaminothiocarbonyl)methylamino]-2-methoxycarbonylbenzenesulfonamide (see tabular Example 2192)
1.2 ml of DBU is added to a suspension of 0.69 g (1.84 mmol) of 5-[N-(ethoxycarbonylaminothiocarbonyl)methylamino]-2-methoxycarbonylbenzenesulfonamide and 0.55 g (1.99 mmol) of 4,6-dimethoxy-2-phenoxycarbonylaminopyrimidine in 5 ml of acetonitrile. The mixture is stirred for 17 h at room temperature and the solvent is then removed by distillation. The residue is taken up in water and washed with diethyl ether. The aqueous phase is acidified with concentrated hydrochloric acid (pH=1) and produces a colorless precipitate, which is filtered off and induced to crystallize by stirring with a little methanol. The resulting product is 0.61 g (60% of theory) of N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-5-[N-(ethoxycarbonylaminothiocarbonyl)methylamino]-2-methoxycarbonylbenzenesulfonamide. m.p.: 144.degree.-145.degree. C.
k) 5-[N-(Acetylmethylamino)-N-(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-2-methoxycarbonylbenzenesulfonamide (see Table 1, Example 89)
0.45 ml of DBU is added to a mixture of 0.75 g (2.6 mmol) of 5-(N-acetylmethylamino)-2-methoxycarbonylbenzenesulfonamide and 0.73 g (2.6 mmol) of 4,6-dimethoxy-2-(phenoxycarbonylamino)pyrimidine in 10 ml of CH.sub.3 CN. The mixture is worked up in analogy to Example j) to give 0.59 g of the desired sulfonylurea, m.p.: 197.degree. C.
l) 2-Methoxycarbonyl-5-(N-methoxycarbonyl-N-methylamino)benzenesulfonyl isocyanate
5.0 g of 2-methoxycarbonyl-5-(N-methoxycarbonyl-N-methylamino)benzenesulfonamide are suspended in 17 ml of 1,2-dichloroethane. 4 ml of thionyl chloride are added and the reaction mixture is heated at boiling for 5 h. The reaction mixture is cooled to room temperature, 0.3 ml of pyridine is added, phosgene is passed into the reaction mixture, and the solution is heated at reflux for 4 h. The reaction mixture is concentrated to give 6.3 g of an oil which is employed directly in the subsequent reaction (Examples m, n, o).
m) 2-Methoxycarbonyl-5-(N-methoxycarbonyl-N-methylamino)-N-[(4,6-dimethylpyrimidin-2-yl)aminocarbonyl]benzenesulfonamide (see Table 1, Example 1,183)
A solution of 2.1 g of 2-methoxycarbonyl-5-(N-methoxycarbonylmethylamino)benzenesulfonyl isocyanate (Example 1)) in 20 ml of dichloroethane is added to a solution of 0.8 g of 2-amino-4,6-dimethylpyrimidine in 20 ml of dichloroethane. The reaction mixture is stirred for 8 h at 40.degree. C. and then concentrated. The residue is induced to form the product by stirring intensively and successively with 1N hydrochloric acid and methanol, to give 0.47 g of the desired sulfonylurea as a solid foam:
.sup.1 H NMR (DMSO, 80 MHz): .delta. (ppm)=2.5 (s, 6H, 2 CH.sub.3), 3.3 (s, 3H, N--CH.sub.3), 3.7 (s, 3H, O--CH.sub.3), 3.9 (s, 3H, OCH.sub.3), 7.0 (s, 1H, H.sub.pyrimidine), 7.8 (s, 2H, 3-H and 4H), 8.1 (s, 1H, 6-H), 10.6 (s, 1H, NH), 13.3 (s, 1H, SO.sub.2 -NH).
n) N-[(4-Chloro-6-methoxypyrimidin-2-yl)aminocarbonyl]-2-methoxycarbonyl-5-(N-methoxycarbonyl-N-methylamino)benzenesulfonamide (see Table 1, Example 1,185)
By analogy with Example m), 0.9 g of 2-amino-4-chloro-6-methoxypyrimidine is reacted with 2.1 g of 2-methoxycarbonyl-5-(N-methoxycarbonyl-N-methylamino)benzenesulfonyl isocyanate (Example 1)). Yield: 0.45 g of the desired sulfonylurea as a solid foam:
.sup.1 H NMR (DMSO, 80 MHz): .delta. (ppm)=3.3 (s, 3H, N-CH.sub.3), 3.7 (s, 3H, O--CH.sub.3), 3.8 (s, 3H, O--CH.sub.3), 4.0 (s, 3H, O--CH.sub.3), 6.8 (s, 1H, H.sub.pyrimidine), 7.7 (s, 2H, 3-H and 4-H), 10.9 (s, 1H, NH), 12.0 (s, 1H, SO.sub.2 -NH).
o) N-[N-(4-Methoxy-6-methyltriazin-2-yl)aminocarbonyl]-2-methoxcarbonyl-5-(N-methoxycarbonyl-N-methylamino)benzenesulfonamide (see Table 1, Example 1,180)
By analogy with Example m), 0.85 g of 2-amino-4-methoxy-6-methyltriazine is reacted with 2.1 g of 2-methoxycarbonyl-5-(N-methoxycarbonyl-N-methylamino)benzenesulfonyl isocyanate (Example 1)). Yield: 0.47 g of the desired sulfonylurea as a solid foam:
.sup.1 H NMR (DMSO, 80 MHz): .delta. (ppm)=2.4 (s, 3H, CH.sub.3), 3.3 (s, 3H, N--CH.sub.3), 3.7 (s, 3H, OCH.sub.3), 3.8 (s, 3H, OCH.sub.3), 4.0 (s, 3H, O--CH.sub.3), 7.8 (s, 2H, 3-H, 4-H), 8.1 (s, 1H, 6-H), 11.0 (s, 1H, NH), 12.3 (s, 14, SO.sub.2 NH).
The remainder of the compounds described in Table 1 are obtained in a manner analogous to Examples a) to o).
The following abbreviations are used in Table 1:
No.=Example number
m.p.=solidification point (melting point) in .degree.C
Me=methyl
Et=ethyl
Pr=n-propyl
n-Pr=n-propyl
i-Pr=i-propyl
c-Pr=cyclopropyl
Bu=butyl
Ph=phenyl.
TABLE 1__________________________________________________________________________ ##STR12##No. R.sup.1 R.sup.2 R.sup.3 R.sup.4 X Y Z m.p.__________________________________________________________________________ 1 Me COCH.sub.2 OMe CO.sub.2 Me H OMe OMe CH 2 Et " " " " " " 3 Me COCH.sub.2 NHCO.sub.2 " " " " " Me 4 Me COCH.sub.2 SMe " " " " " 5 " " " Me " " " 6 " " " H OMe Me N 7 " " " " Me Me CH 8 Et " " " " " " 9 " " " " OMe " N 10 " " " " OMe OMe N 11 Me CHO " " OMe OMe CH 177-182 12 " " " " OMe OMe N 13 " " " " OMe Me N 14 " " " " OMe Me CH 15 " " " " NMe.sub.2 OCH.sub.2 CF.sub.3 N 16 " " " " Me Me CH 17 " " " " Me Me N 18 " " " " Cl OMe CH 19 " " " Me OMe OMe CH 20 " " " Me OMe Me N 21 " " CO.sub.2 Et H OMe OMe CH 22 " " " " OMe Cl CH 23 " " " " Me Me CH 24 " " " " OMe Me N 25 " " " " NMe.sub.2 OCH.sub.2 CF.sub.3 N 26 " " " Me OMe OMe CH 27 " " " Me OMe Me N 28 " " CO.sub.2 -n-Pr H OMe OMe CH 29 " " " " OMe OMe N 30 " " " " OMe Me N 31 " " " " Me Me CH 32 " " " " OMe Cl CH 33 " " " Me Me OMe N 34 " " " Me OMe OMe CH 35 Me CHO CO.sub.2 -i-Pr H OMe OMe CH 36 " " " " OMe OMe N 37 " " " " OMe Me N 38 " " " " OMe Cl CH 39 " " " " Me Me CH 40 " " " " SMe NEt.sub.2 N 41 " " CO.sub.2 -i-Pr Me OMe Me N 42 " " " Me OMe OMe CH 43 Me CHO CO.sub.2 -Allyl H OMe OMe CH 44 Et CHO CO.sub.2 Me H OMe OMe CH 45 " " " " OMe Me N 46 " " " " Me Me CH 47 " " " " Cl OMe CH 48 " " " Me OMe OMe CH 49 " " " Me OMe Me N 50 " " CO.sub.2 Et H OMe OMe CH 51 " " " " OMe Me CH 52 " " " " Cl OMe CH 53 " " " " OMe Me N 54 " " " Me OMe OMe CH 55 " " " Me OMe Me N 56 " " CO.sub.2 -n-Pr H OMe OMe CH 57 " " " " OMe Me N 58 " " " " OMe Cl CH 59 " " " " Me Me CH 60 " " " Me OMe OMe CH 61 " " " Me OMe Me N 62 " " CO.sub.2 -i-Pr H OMe OMe CH 63 " " " " OMe Me N 64 " " " " Me Me CH 65 " " " Me OMe Me N 66 n-Pr CHO CO.sub.2 Me H OMe OMe CH 67 " " " " OMe Cl CH 68 " " " " Me Me CH 69 " " " " OMe Me N 70 " " " Me OMe OMe CH 71 " " " Me OMe Me N 72 n-Pr " CO.sub.2 Et H OMe Me N 73 " " " " OMe OMe CH 74 " " " " Me Me CH 75 " " CO.sub.2 n-Pr " OMe OMe CH 76 i-Pr " CO.sub.2 Me H OMe OMe CH 77 " " " " OMe Me N 78 " " " " Me Me CH 79 " " " " Cl OMe N 80 " " " Me OMe Me N 81 " " " Me OMe OMe CH 82 Allyl " CO.sub.2 Me H OMe OMe CH 83 " " " " OMe Cl CH 84 " " " " Me Me CH 85 " " " " OMe Me N 86 " " CO.sub.2 Et " OMe OMe CH 87 " " CO.sub.2 n-Pr " OMe OMe CH 88 " " CO.sub.2 i-Pr " OMe OMe CH 89 Me COCH.sub.3 CO.sub.2 Me " OMe OMe CH 197.degree. C. 90 " " " " OMe OMe N 91 " " " " OMe Me N 92 " " " " OMe Me CH 93 " " " " NMe.sub.2 OCH.sub.2 CF.sub.3 N 94 " " " " Me Me CH 95 " " " " Me Me N 96 " " " " Cl OMe CH 97 " " " Me OMe OMe CH 98 " " " Me OMe Me N 99 " " CO.sub.2 Et H OMe OMe CH100 " " " " OMe Cl CH101 " " " " Me Me CH102 " " " " OMe Me N103 " " " " NMe.sub.2 OCH.sub.2 CF.sub.3 N104 " " " Me OMe OMe CH105 " " " Me OMe Me N106 " " CO.sub.2 -n-Pr H OMe OMe CH107 " " " " OMe OMe N "108 " " " " OMe Me N109 " " " " Me Me CH110 " " " " OMe Cl CH111 " " " Me Me OMe N112 " " " Me OMe OMe CH113 Me COCH.sub.3 CO.sub.2 -i-Pr H OMe OMe CH114 " " " " OMe OMe N115 " " " " OMe Me N116 " " " " OMe Cl CH117 " " " " Me Me CH118 " " " " SMe NEt.sub.2 N119 " " CO.sub.2 -i-Pr Me OMe Me N120 " " " Me OMe OMe CH121 Me COCH.sub.3 CO.sub.2 -Allyl H OMe OMe CH122 Et " CO.sub.2 Me H OMe OMe CH123 " " " " OMe Me N124 " " " " Me Me CH125 " " " " Cl OMe CH126 " " " Me OMe OMe CH127 " " " Me OMe Me N128 " " CO.sub.2 Et H OMe OMe CH129 " " " " OMe Me CH130 " " " " Cl OMe CH131 " " " " OMe Me N132 " " " Me OMe OMe CH133 " " " Me OMe Me N134 " " CO.sub.2 -n-Pr H OMe OMe CH135 " " " " OMe Me N136 " " " " OMe Cl CH137 " " " " Me Me CH138 " " " Me OMe OMe CH139 " " " Me OMe Me N140 " " CO.sub.2 -i-Pr H OMe OMe CH141 " " " " OMe Me N142 " " " " Me Me CH143 " " " Me OMe Me N144 n-Pr COCH.sub.3 CO.sub.2 Me H OMe OMe CH 160.degree. C.145 " " " " OMe Cl CH146 " " " " Me Me CH147 " " " " OMe Me N148 " " " Me OMe OMe CH149 " " " Me OMe Me N150 n-Pr " CO.sub.2 Et H OMe Me N151 " " " " OMe OMe CH152 " " " " Me Me CH153 " " CO.sub.2 -n-Pr " OMe OMe CH154 i-Pr " CO.sub.2 Me H OMe OMe CH155 " " " " OMe Me N156 " " " " Me Me CH157 " " " " Cl OMe N158 " " " Me OMe Me N159 " " " Me OMe OMe CH160 Allyl " CO.sub.2 Me H OMe OMe CH161 " " " " OMe Cl CH162 " " " " Me Me CH163 " " " " OMe Me N164 " " CO.sub.2 Et H OMe OMe CH165 " " CO.sub.2 -n-Pr " OMe OMe CH166 " " CO.sub.2 -i-Pr " OMe OMe CH167 Me COCH.sub.2 CH.sub.3 CO.sub.2 Me H OMe OMe CH168 " " " " OMe OMe N169 " " " " SMe Me N170 " " " " OMe Me N171 " " " " OMe Me CH172 " " " " NMe.sub.2 OCH.sub.2 CF.sub.3 N173 " " " " Me Me CH174 " " " " Me Me N175 " " " " Cl OMe CH176 " " " Me OMe OMe CH177 " " CO.sub.2 Me Me OMe Me N178 " " CO.sub.2 Et H OMe OMe CH179 " " " " OMe Cl CH180 " " " " Me Me CH181 " " " " OMe Me N182 " " " " NMe.sub.2 OCH.sub.2 CF.sub.3 N183 " " " Me OMe OMe CH184 " " " Me OMe Me N185 " " CO.sub.2 -n-Pr H OMe OMe CH186 " " " " OMe OMe N187 " " " " OMe Me N188 " " " " Me Me CH189 " " " " OMe Cl CH190 " " " Me Me OMe N191 " " " " OMe OMe CH192 Me COCH.sub.2 CH.sub.3 CO.sub.2 -i-Pr H OMe OMe CH201 Et " CO.sub.2 -Me H OMe OMe CH202 " " " " OMe Me N203 " " " " Me Me CH204 " " " " Cl OMe CH205 " " " Me OMe OMe CH206 " " " " OMe Me N207 " " CO.sub.2 Et H OMe OMe CH193 " " " " OMe OMe N194 " " " " OMe Me N195 " " " " OMe Cl CH196 " " " " Me Me CH197 " " " " SMe NEt.sub.2 N198 " " " Me OMe Me N199 " " " " OMe OMe CH200 Me COCH.sub.2 CH.sub.3 CO.sub.2 -Allyl H OMe OMe CH208 " " " " OMe Me CH209 " " " " Cl OMe CH210 " " " " OMe Me N211 " " " Me OMe OMe CH212 " " " " " Me N213 " " CO.sub.2 -n-Pr H OMe OMe CH214 " " " " OMe Me N215 " " " " OMe Cl CH216 " " " " Me Me CH217 " " " Me OMe OMe CH218 " " " " OMe Me N219 " " CO.sub.2 -i-Pr H OMe OMe CH220 " " " " OMe Me N221 " " " " Me Me CH222 " " " Me OMe Me N223 n-Pr COCH.sub.2 CH.sub.3 CO.sub.2 Me H OMe OMe CH224 " " " " OMe Cl CH225 " " " " Me Me CH226 " " " " OMe Me N227 " " " Me OMe OMe CH228 " " " Me OMe Me N229 n-Pr " CO.sub.2 Et H OMe Me N230 " " " " OMe OMe CH231 " " " " Me Me CH232 " " CO.sub.2 -n-Pr " OMe OMe CH233 i-Pr " CO.sub.2 Me H OMe OMe CH234 " " " " OMe Me N235 " " " " Me Me CH236 " " " " Cl OMe N237 " " " Me OMe Me N238 " " " Me OMe OMe CH239 Allyl " CO.sub.2 Me H OMe OMe CH240 " " " " OMe Cl CH241 " " " " Me Me CH242 " " " " OMe Me N243 " " CO.sub.2 Et H OMe OMe CH244 " " CO.sub.2 -n-Pr " OMe OMe CH245 " " CO.sub.2 -i-Pr " OMe OMe CH246 Me CO-n-Pr CO.sub.2 Me H OMe OMe CH247 " " " " OMe OMe N248 " " " " OMe Me N249 " " " " OMe Me CH250 " " " " NMe.sub.2 OCH.sub.2 CF.sub.3 N251 " " " " Me Me CH252 " " " " Me Me N253 " " " " Cl OMe CH254 " " " Me OMe OMe CH255 " " " Me OMe Me N256 " " CO.sub.2 Et H OMe OMe CH257 " " " " OMe Cl CH258 " " " " Me Me CH259 " " " " OMe Me N260 " " " " NMe.sub.2 OCH.sub.2 CF.sub.3 N261 " " " Me OMe OMe CH262 " " " Me OMe Me N263 " " CO.sub.2 -n-Pr H OMe OMe N264 " " " " OMe OMe CH265 Me CO-n-Pr CO.sub.2 -n-Pr H OMe OMe CH266 " " " " OMe OMe N267 " " " " OMe Cl CH268 " " " Me Me OMe N269 " " " Me OMe OMe CH270 Me CO-n-Pr CO.sub.2 -i-Pr H OMe OMe CH271 " " " " OMe OMe N272 " " " " OMe Me N273 " " " " OMe Cl CH274 " " " " Me Me CH275 " " " " SMe NEt.sub.2 N276 " " CO.sub.2 -i-Pr Me OMe Me N277 " " " Me OMe OMe CH278 Me " CO.sub.2 -Allyl H OMe OMe CH279 Et " CO.sub.2 Me H OMe OMe CH280 " " " " OMe Me N281 " " " " Me Me CH282 " " " " Cl OMe CH283 " " " Me OMe OMe CH284 " " " Me OMe Me N285 " " CO.sub.2 Et H OMe OMe CH286 " " " " OMe Me CH287 " " " " Cl OMe CH288 " " " " OMe Me N289 " " " Me OMe OMe CH290 " " " Me OMe Me N291 " " CO.sub.2 -n-Pr H OMe OMe CH292 " " " " OMe Me N293 " " " " OMe Cl CH294 " " " " Me Me CH295 " " " Me OMe OMe CH296 " " " Me OMe Me N297 " " CO.sub.2 -i-Pr H OMe OMe CH298 " " " " OMe Me N299 n-Pr CO-n-Pr CO.sub.2Me H OMe OMe CH300 " " " " OMe Cl CH301 " " " " Me Me CH302 " " " " OMe Me N303 " " " Me OMe OMe CH304 " " " Me OMe Me N305 n-Pr " CO.sub.2 Et H OMe Me N306 " " " " OMe OMe CH307 " " " " Me Me CH308 " " CO.sub.2 -n-Pr " OMe OMe CH309 i-Pr " CO.sub.2 Me H OMe OMe CH310 " " " " OMe Me N311 " " " " Me Me CH312 " " " " Cl OMe N313 " " " Me OMe Me N314 " " " Me OMe OMe CH315 Allyl " CO.sub.2Me H OMe OMe CH316 " " " " OMe Cl CH317 " " " " Me Me CH318 " " " " OMe Me N319 " " CO.sub.2 Et H OMe OMe CH320 " " CO.sub.2 -n-Pr " OMe OMe CH321 " " CO.sub.2 -i-Pr " OMe OMe CH322 Me CO-i-Pr CO.sub.2Me H OMe OMe CH323 " " " " OMe OMe N324 " " " " " Me N325 " " " " " " CH326 " " " " NMe.sub.2 OCH.sub.2 CF.sub.3 N327 " " " " Me Me CH328 " " " " Me Me N329 " " " " Cl OMe CH330 " " " Me OMe OMe CH331 " " " " " Me N332 " " CO.sub.2Et H OMe OMe CH333 " " " " " Cl CH334 " " " " Me Me CH335 " " " " OMe Me N336 " " " " NMe.sub.2 OCH.sub.2 CF.sub.3 N337 " " " Me OMe OMe CH338 " " " " OMe Me N339 " " CO.sub.2 -n-Pr H OMe OMe CH340 " " " " " " N341 " " " " OMe Me N342 " " " " Me Me CH343 " " " " OMe Cl CH344 " " " Me Me OMe N345 " " " " OMe OMe CH346 Me CO-i-Pr CO.sub.2 -i-Pr H OMe OMe CH347 " " " " " " N348 " " " " OMe Me N349 " " " " OMe Cl CH350 " " " " Me Me CH351 " " " " SMe NEt.sub.2 N352 " " CO.sub.2 -i-Pr Me OMe Me N353 " " " " OMe OMe CH354 Me COCHMe.sub.2 CH.sub.2 CHCH.sub.2 H OMe OMe CH355 Et " CO.sub.2Me H OMe OMe CH356 " " " H OMe Me N357 " " " " Me Me CH358 " " " " Cl OMe CH359 " " " Me OMe OMe CH360 " " " " OMe Me N361 " " CO.sub.2Et H OMe OMe CH362 " " " " OMe Me CH363 " " " " Cl OMe CH364 " " " " OMe Me N365 " " " Me OMe OMe CH366 " " " " " Me N367 " " CO.sub.2 -n-Pr H OMe OMe CH368 " " " " OMe Me N369 " " " " OMe Cl CH370 " " " " Me Me CH371 " " " Me OMe OMe CH372 " " " " OMe Me N373 " " CO.sub.2 -i-Pr H OMe OMe CH374 " " " " OMe Me N375 " " " " Me Me CH376 " " " Me OMe Me N377 n-Pr CO-i-Pr CO.sub.2Me H OMe OMe CH378 " " " " " Cl CH379 " " " " Me Me CH380 " " " " OMe Me N381 " " " Me OMe OMe CH382 " " " " OMe Me N383 n-Pr " CO.sub.2Et H " Me N384 " " " " " OMe CH385 " " " " Me Me CH386 " " CO.sub.2 -n-Pr " OMe OMe CH387 i-Pr " CO.sub.2Me H OMe OMe CH388 " " " " OMe Me N389 " " " " Me Me CH390 " " " " Cl OMe N391 " " " Me OMe Me N392 " " " " " OMe CH393 Allyl " CO.sub.2Me H OMe OMe CH394 " " " " " Cl CH395 " " " " Me Me CH396 " " " " OMe Me N397 " " CO.sub.2Et H OMe OMe CH398 " " CO.sub.2 -n-Pr " OMe OMe CH399 " " CO.sub.2 -i-Pr " " " "400 Me CO-t-Bu CO.sub.2Me H OMe OMe CH401 " " " " " OMe N402 " " " " " Me N403 " " " " " " CH404 " " " " NMe.sub.2 OCH.sub.2 CF.sub.3 N405 " " " " Me Me CH406 " " " " " " N407 " " " " Cl OMe CH408 " " " Me OMe OMe CH409 " " " " " Me N410 " " CO.sub.2Et H OMe OMe CH411 " " " " " Cl CH412 " " " " Me Me CH413 " " " " OMe Me N414 " " " " NMe.sub.2 OCH.sub.2 CF.sub.3 N415 " " " Me OMe OMe CH416 " " " " OMe Me N417 " " CO.sub.2 -n-Pr H OMe OMe CH418 " " " " " " N419 " " " " OMe Me N420 " " " " Me Me CH421 " " " " OMe Cl CH422 " " " Me Me OMe N423 " " " " OMe OMe CH424 Me CO-t-Bu CO.sub.2 -i-Pr H OMe OMe CH425 " " " " " " N426 " " " " H Me N427 " " " " OMe Cl CH428 " " " " Me Me CH429 " " " " SMe NEt.sub.2 N430 " " CO.sub.2 -i-Pr Me OMe Me N431 " " " Et OMe OMe CH432 Me " CO.sub.2 -Allyl H OMe OMe CH433 Et " CO.sub.2Me H OMe OMe CH434 " " " H OMe Me N435 " " " " Me Me CH436 " " " " Cl OMe CH437 " " " Me OMe OMe CH438 " " " " OMe Me N439 " " CO.sub.2Et H OMe OMe CH440 " " " " OMe Me CH441 " " " " Cl OMe CH442 " " " " OMe Me N443 " " " Me OMe OMe CH444 " " " " " Me N445 " " CO.sub.2 -n-Pr H OMe OMe CH446 " " " " OMe Me N447 " " " " OMe Cl CH448 " " " " Me Me CH449 " " " Me OMe OMe CH450 " " " " OMe Me N451 " " CO.sub.2 -iPr H OMe OMe CH452 " " " " OMe Me N453 " " " " Me Me CH454 " " " Me OMe Me N455 n-Pr CO-t-Bu CO.sub.2Me H OMe OMe CH456 " " " " OMe Cl CH457 " " " " Me Me CH458 " " " " OMe Me N459 " " " Me OMe OMe CH460 n-Pr " CO.sub.2Et Me OMe Me N461 n-Pr " CO.sub.2Et H OMe Me N462 " " " " OMe OMe CH463 " " " " Me Me CH464 i-Pr " CO.sub.2Me " OMe OMe CH465 i-Pr " " Me OMe OMe CH466 " " " H OMe Me N467 " " " " Me Me CH468 " " " " Cl OMe N469 " " " Me OMe Me N470 Allyl " " H OMe OMe CH471 " " " H OMe Cl CH472 " " " " OMe Me N473 " " " " Me Me CH474 " " CO.sub.2Et H OMe OMe CH475 " " CO.sub.2 -n-Pr H OMe OMe CH476 " " CO.sub.2 -i-Pr H OMe OMe CH477 Me CO-c-Propyl CO.sub.2Me H OMe OMe CH 161.degree. C.478 " " " " " OMe N479 " " " " " Me N480 " " " " " " CH481 " " " " NMe.sub.2 OCH.sub.2 CF.sub.3 N482 " " " " Me Me CH483 " " " " " " N484 " " " " Cl OMe CH485 " " " Me OMe OMe CH486 " " " " " Me N48 " " CO.sub.2Et H OMe OMe CH488 " " " " " Cl CH489 " " " " Me Me CH490 " " " " OMe Me N491 " " " " NMe.sub.2 OCH.sub.2 CF.sub.3 N492 " " " Me OMe OMe CH493 " " " " OMe Me N494 " " CO.sub.2 -n-Pr H OMe OMe CH495 " " " " " " N496 " " " " OMe Me N497 " " " " Me Me CH498 " " " " OMe Cl CH499 " " " Me Me OMe N500 " " " " OMe OMe CH501 Me CO-c-Propyl CO.sub.2 -i-Pr H OMe OMe CH502 " " " " " " N503 " " " " OMe Me N504 " " " " OMe Cl CH505 " " " " Me Me CH506 " " " " SMe NEt.sub.2 N507 " " CO.sub.2 -i-Pr Me OMe Me N508 " " " " OMe OMe CH509 Me " CO.sub.2 -Allyl H OMe OMe CH510 Et " CO.sub.2Me H OMe OMe CH511 " " " H OMe Me N512 " " " " Me Me CH513 " " " " Cl OMe CH514 " " " Me OMe OMe CH515 " " " " OMe Me N516 " " CO.sub.2Et H OMe OMe CH517 " " " " Me Me CH518 " " " " Cl OMe CH519 " " " " OMe Me N520 " " " Me OMe OMe CH521 " " " " " Me N522 " " CO.sub.2 -n-Pr H OMe OMe CH523 " " " " OMe Me N524 " " " " OMe Cl CH525 " " " " Me Me CH526 " " " Me OMe OMe CH527 " " " " OMe Me N528 " " CO.sub.2 -i-Pr H OMe OMe CH529 " " " " OMe Me N530 " " " " Me Me CH531 " " " Me OMe Me N532 n-Pr CO-c-Propyl CO.sub.2Me H OMe OMe CH533 " " " " " Cl CH534 " " " " Me Me CH535 " " " " OMe Me N536 " " " Me OMe OMe CH537 " " " " OMe Me N538 n-Pr " CO.sub.2Et H " " N539 " " " " " OMe CH540 " " " " Me Me CH541 " " CO.sub.2 -n-Pr " OMe OMe CH542 i-Pr " CO.sub.2Me H OMe OMe CH543 " " " " OMe Me N544 " " " " Me Me CH545 " " " " Cl OMe N546 " " " Me OMe Me N547 " " " " " OMe CH548 Allyl " CO.sub.2Me H OMe OMe CH549 " " " " " Cl CH550 " " " " Me Me CH551 " " " " OMe Me N552 " " CO.sub.2Et H OMe OMe CH553 " " CO.sub.2 -n-Pr H OMe OMe CH554 " " CO.sub.2 -i-Pr H OMe OMe CH555 Me CO-n-C.sub.5 H.sub.11 CO.sub.2Me H OMe OMe CH556 " " " " OMe OMe N557 " " " " " Me N558 " " " " " " CH559 " " " " NMe.sub.2 OCH.sub.2 CF.sub.3 N560 " " " " Me Me CH561 " " " " " " N562 " " " " Cl OMe CH563 " " " Me OMe OMe CH564 " " " " " Me N565 " " CO.sub.2Et H OMe OMe CH566 " " " " " Cl CH567 " " " " Me Me CH568 " " " " OMe Me N569 " " " " NMe.sub.2 OCH.sub.2 CF.sub.3 N570 " " " Me OMe OMe CH571 " " " " OMe Me N572 " " CO.sub.2 -n-Pr H OMe OMe CH573 " " " " " " N574 " " " " OMe Me N575 " " " " Me Me CH576 " " " " OMe Cl CH577 " " " Me Me OMe N578 " " " " OMe OMe CH579 Me CO-n-C.sub.5 H.sub.11 CO.sub.2 -i-Pr H OMe OMe CH580 " " " " " " N581 " " " " H Me N582 " " " " OMe Cl CH583 " " " " Me Me CH584 " " " " SMe NEt.sub.2 N585 " " CO.sub.2 -i-Pr Me OMe Me N586 " " " " OMe OMe CH587 Me " CO.sub.2 -Allyl H OMe OMe CH588 Et " CO.sub.2Me H OMe OMe CH589 " " " H OMe Me N590 " " " " Me Me CH591 " " " " Cl OMe CH592 " " " Me OMe OMe CH593 " " " " OMe Me N594 " " CO.sub.2Et H OMe OMe CH595 " " " " OMe Me CH596 " " " " Cl OMe CH597 " " " " OMe Me N598 " " " Me OMe OMe CH599 " " " " " Me N600 " " CO.sub.2 -n-Pr H OMe OMe CH601 " " " " OMe Me N602 " " " " OMe Cl CH603 " " " " Me Me CH604 " " " Me OMe OMe CH605 " " " " OMe Me N606 " " CO.sub.2 -i-Pr H OMe OMe CH607 " " " " OMe Me N608 " " " " Me Me CH609 " " " Me OMe Me N610 n-Pr CO-n-C.sub.5 H.sub.11 CO.sub.2Me H OMe OMe CH611 " " " " " Cl CH612 " " " " Me Me CH613 " " " " OMe Me N614 " " " Me OMe OMe CH615 " " " " OMe Me N616 n-Pr " CO.sub.2Et H OMe Me N617 " " " " " OMe CH618 " " " " Me Me CH619 " " CO.sub.2 -n-Pr " OMe OMe CH620 i-Pr " CO.sub.2Me H OMe OMe CH621 " " " " OMe Me N622 " " " " Me Me CH623 " " " " Cl OMe N624 " " " Me OMe N625 " " " " " OMe CH626 Allyl " CO.sub.2Me H OMe OMe CH627 " " " " " Cl CH628 " " " " Me Me CH629 " " " " OMe Me N630 " " CO.sub.2Et H OMe OMe CH631 " " CO.sub.2 -n-Pr " " " CH632 " " CO.sub.2 -i-Pr " " " "633 Me COCHMeEt CO.sub.2Me H OMe OMe CH634 " " " " " OMe N635 " " " " " Me N636 " " " " " " CH637 " " " " NMe.sub.2 OCH.sub.2 CF.sub.3 N638 " " " " Me Me CH639 " " " " " " N640 " " " " Cl OMe CH641 " " " Me OMe OMe CH642 " " " " " Me N643 " " CO.sub.2Et H OMe OMe CH644 " " " " " Cl CH645 " " " " Me Me CH646 " " " " OMe Me N647 " " " " NMe.sub.2 OCH.sub.2 CF.sub.3 N648 " " " Me OMe OMe CH649 " " " " OMe Me N650 " " CO.sub.2 -n-Pr H OMe OMe CH651 " " " " " " N652 " " " " OMe Me N653 " " " " Me Me CH654 " " " " OMe Cl CH655 " " " Me Me OMe N656 " " " " OMe OMe CH657 Me COCHMeEt CO.sub.2 -i-Pr H OMe OMe CH658 " " " " " " N659 " " " " OMe Me N660 " " " " OMe Cl CH661 " " " " Me Me CH662 " " " " SMe NEt.sub.2 N663 " " CO.sub.2 -i-Pr Me OMe Me N664 " " " " OMe OMe CH665 Me " CO.sub.2 -Allyl H OMe OMe CH666 Et " CO.sub.2Me H OMe OMe CH667 " " " H OMe Me N668 " " " " Me Me CH669 " " " " Cl OMe CH670 " " " Me OMe OMe CH671 " " " " OMe Me N672 " " CO.sub.2Et H OMe OMe CH673 " " " " OMe Me CH674 " " " " Cl OMe CH675 " " " " OMe Me N676 " " " Me OMe OMe CH677 " " " " " Me N678 " " CO.sub.2 -n-Pr H OMe OMe CH679 " " " " OMe Me N680 " " " " OMe Cl CH681 " " " " Me Me CH682 " " " Me OMe OMe CH683 " " " " OMe Me N684 " " CO.sub.2 -i-Pr H OMe OMe CH685 " " " " OMe Me N686 " " " " Me Me CH687 " " " Me OMe Me N688 n-Pr COCHMeEt CO.sub.2Me H OMe OMe CH689 " " " " " Cl CH690 " " " " Me Me CH691 " " " " OMe Me N692 " " " Me OMe OMe CH693 " " " " OMe Me N694 n-Pr " CO.sub.2Et H " " N695 " " " " " OMe CH696 " " " " Me Me CH697 " " CO.sub.2 -n-Pr " OMe OMe CH698 i-Pr " CO.sub.2Me H OMe OMe CH699 " " " " OMe Me N700 " " " " Me Me CH701 " " " " Cl OMe N702 " " " Me OMe Me N703 " " " " " OMe CH704 Allyl " CO.sub.2Me H OMe OMe CH705 " " " " " Cl CH706 " " " " Me Me CH707 " " " " OMe Me N708 " " CO.sub.2Et H OMe OMe CH709 " " CO.sub.2 -n-Pr " " " CH710 " " CO.sub.2 -i-Pr " " " CH711 Me ##STR13## CO.sub.2Me H OMe OMe CH712 " " " " OMe OMe N713 " " " " " Me N714 " " " " " " CH715 " " " " NMe.sub.2 OCH.sub.2 CF.sub.3 N716 " " " " Me Me CH717 " " " " " " N718 " " " " Cl OMe CH719 " " " Me OMe OMe CH720 " " " " " Me N721 " " CO.sub.2Et H OMe OMe CH722 " " " " " Cl CH723 " " " " Me Me CH724 " " " " OMe Me N725 " " " " NMe.sub.2 OCH.sub.2 CF.sub.3 N726 " " " Me OMe OMe CH727 " " " " OMe Me N728 " " CO.sub.2 -n-Pr H OMe OMe CH729 " " " " " " N730 " " " " OMe Me N731 " " " " Me Me CH732 " " " " OMe Cl CH733 " " " Me Me OMe N734 " " " " OMe OMe CH735 Me ##STR14## CO.sub.2 -i-Pr H OMe OMe CH736 " " " " " " N737 " " " " OMe Me N738 " " " " OMe Cl CH739 " " " " Me Me CH740 " " " " SMe NEt.sub.2 N741 " " CO.sub.2 -i-Pr Me OMe Me N742 " " " " OMe OMe CH743 Me " CO.sub.2 -Allyl H OMe OMe CH744 Et " CO.sub.2Me H OMe OMe CH745 " " " H OMe Me N746 " " " " Me Me CH747 " " " " Cl OMe CH748 " " " Me OMe OMe CH749 " " " " OMe Me N750 " " CO.sub.2Et H OMe OMe CH751 " " " " OMe Me CH752 " " " " Cl OMe CH753 " " " " OMe Me N754 " " " Me OMe OMe CH755 " " " " " Me N756 " " CO.sub.2 -n-Pr H OMe OMe CH757 " " " " OMe Me N758 " " " " OMe Cl CH759 " " " " Me Me CH760 " " " Me OMe OMe CH761 " " " " OMe Me N762 " " CO.sub.2 -i-Pr H OMe OMe CH763 " " " " OMe Me N764 " " " " Me Me CH765 " " " Me OMe Me N766 n-Pr ##STR15## CO.sub.2Me H OMe OMe CH767 " " " " " Cl CH768 " " " " Me Me CH769 " " " " OMe Me N770 " " " Me OMe OMe CH771 " " " " OMe Me N772 n-Pr " CO.sub.2Et H OMe OMe N773 " " " " " OMe CH774 " " " " Me Me CH775 " " CO.sub.2 -n-Pr " OMe OMe CH776 i-Pr " CO.sub.2Me H OMe OMe CH777 " " " " OMe Me N778 " " " " Me Me CH779 " " " " Cl OMe N780 " " " Me OMe Me N781 " " " " " OMe CH782 Allyl " CO.sub.2Me H OMe OMe CH783 " " " " Cl CH784 " " " " Me Me CH785 " " " " OMe Me N786 " " CO.sub.2Et H OMe OMe CH787 " " CO.sub.2 -n-Pr " " " "788 " " CO.sub.2 -i-pr " " " "789 Me ##STR16## CO.sub.2 Me H OMe OMe CH790 " " " " " OMe N791 " " " " " Me N792 " " " " " " CH793 " " " " NMe.sub.2 OCH.sub.2 CF.sub.3 N794 " " " " Me Me CH795 " " " " " " N796 " " " " Cl OMe CH797 " " " Me OMe OMe CH798 " " " " " Me N799 " " CO.sub.2Et H OMe OMe CH800 " " " " " Cl CH801 " " " " Me Me CH802 " " " " OMe Me N803 " " " " NMe.sub.2 OCH.sub.2 CF.sub.3 N804 " " " Me OMe OMe CH805 " " " " OMe Me N806 " " CO.sub.2 -n-Pr H OMe OMe CH807 " " " " " " N808 " " " " OMe Me N809 " " " " Me Me CH810 " " " " OMe Cl CH811 " " " Me Me OMe N812 " " " " OMe OMe CH813 Me " CO.sub.2 -i-Pr H OMe OMe CH814 " " " " " " N815 " " " " OMe Me N816 " " " " OMe Cl CH817 " " " " Me Me CH818 " " " " SMe NEt.sub.2 N819 " " CO.sub.2 -i-Pr Me OMe Me N820 " " " " OMe OMe CH821 Me " CO.sub.2 -Allyl H OMe OMe CH822 Et " CO.sub.2Me H OMe OMe CH823 " " " H OMe Me N824 " " " " Me Me CH825 " " " " Cl OMe CH826 " " " Me OMe OMe CH827 " " " " OMe Me N828 " " CO.sub.2Et H OMe OMe CH829 " " " " OMe Me CH830 " " " " Cl OMe CH831 " " " " OMe Me N832 " " " Me OMe OMe CH833 " " " " " Me N834 " " CO.sub.2 -n-Pr H OMe OMe CH835 " " " " OMe Me N836 " " " " OMe Cl CH837 " " " " Me Me CH838 " " " Me OMe OMe CH839 " " " " OMe Me N840 " " CO.sub.2 -i-Pr H OMe OMe CH841 " " " " OMe Me N842 " " " " Me Me CH843 " " " Me OMe Me N844 n-Pr " CO.sub.2Me H OMe OMe CH845 " " " " " Cl CH846 " " " " Me Me CH847 " " " " OMe Me N848 " " " Me OMe OMe CH849 " " " " OMe Me N850 n-Pr " CO.sub.2Et H " " N851 " " " " " OMe CH852 " " " " Me Me CH853 " " CO.sub.2 -n-Pr " OMe OMe CH854 i-Pr " CO.sub.2Me H OMe OMe CH855 " " " " OMe Me N856 " " " " Me Me CH857 " " " " Cl OMe N858 " " " Me OMe Me N859 " " " " " OMe CH860 Allyl " CO.sub.2Me H OMe OMe CH861 " " " " " Cl CH862 " " " " Me Me CH863 " " " " OMe Me N864 " " CO.sub.2Et H OMe OMe CH865 " " CO.sub.2 -n-Pr H OMe OMe CH__________________________________________________________________________
__________________________________________________________________________No. R.sup.1 R.sup.2 R.sup.3 R.sup.4 X Y Z m.p.__________________________________________________________________________866 " " CO.sub.2 -i-Pr " " " CH867 Me ##STR17## CO.sub.2 Me H OMe OMe CH868 " " " " " OMe N869 " " " " " Me N870 " " " " " " CH871 " " " " NMe.sub.2 OCH.sub.2 CF.sub.3 N872 " " " " Me Me CH873 " " " " " Cl N874 " " " " Cl OMe CH875 " " " Me OMe OMe CH876 " " " " " Me N877 " " CO.sub.2 Et H OMe OMe CH878 " " " " " Cl CH879 " " " " Me Me CH880 " " " " OMe Me N881 " " " " NMe.sub.2 OCH.sub.2 CF.sub.3 N882 " " " Me OMe OMe CH883 " " " " OMe Me N884 " " CO.sub.2 -n-Pr H OMe OMe CH885 " " " " " " N886 " " " " OMe Me N887 " " " " Me Me CH888 " " " " OMe Cl CH889 " " " Me Me OMe N890 " " " " OMe OMe CH891 Me " CO.sub.2 -i-Pr H OMe OMe CH892 " " " " " " N893 " " " " H Me N894 " " " " OMe Cl CH895 " " " " Me Me CH896 " " " " SMe NEt.sub.2 N897 " " CO.sub.2 -i-Pr Me OMe Me N898 " " " " OMe OMe CH899 Me " CO.sub.2 -Allyl H OMe OMe CH900 Et " CO.sub.2 Me H OMe OMe CH901 " " " H OMe Me N902 " " " " Me Me CH903 " " " " Cl OMe CH904 " " " Me OMe OMe CH905 " " " " OMe Me N906 " " CO.sub.2 Et H OMe OMe CH907 " " " " OMe Me CH908 " " " " Cl OMe CH909 " " " " OMe Me N910 " " " Me OMe OMe CH911 " " " " " Me N912 " " CO.sub.2 -n-Pr H OMe OMe CH913 " " " " OMe Me N914 " " " " OMe Cl CH915 " " " " Me Me CH916 " " " Me OMe OMe CH917 " " " " OMe Me N918 " " CO.sub.2 -i-Pr H OMe OMe CH919 " " " " OMe Me N920 " " " " Me Me CH921 " " " Me OMe Me N922 n-Pr " CO.sub.2 Me H OMe OMe CH923 " " " " " Cl CH924 " " " " Me Me CH925 " " " " OMe Me N926 " " " Me OMe OMe CH927 " " " " OMe Me N928 n-Pr " CO.sub.2 Et H " " N929 " " " " " OMe CH930 " " " " Me Me CH931 " " CO.sub.2 -n-Pr " OMe OMe CH932 i-Pr " CO.sub.2 Me H OMe OMe CH933 " " " " OMe Me N934 " " " " Me Me CH935 " " " " Cl OMe N936 " " " Me OMe Me N937 " " " " " OMe CH938 Allyl " CO.sub.2 Me H OMe OMe CH939 " " " " " Cl CH940 " " " " Me Me CH941 " " " " OMe Me N942 " " CO.sub.2 Et H OMe OMe CH943 " " CO.sub.2 -n-Pr " " " CH944 " " CO.sub.2 -i-Pr " " " "945 Me ##STR18## CO.sub.2 Me H OMe OMe CH946 " " " " " OMe N947 " " " " " Me N948 " " " " " " CH949 " " " " NMe.sub.2 OCH.sub.2 CF.sub.3 N950 " " " " Me Me CH951 " " " " " " N952 " " " " Cl OMe CH953 " " " Me OMe OMe CH954 " " " " " Me N955 " " CO.sub.2 Et H OMe OMe CH956 " " " " " Cl CH957 " " " " Me Me CH958 " " " " OMe Me N959 " " " " NMe.sub.2 OCH.sub.2 CF.sub.3 N960 " " " Me OMe OMO CH961 " " " " OMe Me N962 " " CO.sub.2 -n-Pr H OMe OMe CH963 " " " " " " N964 " " " " OMe Me N965 " " " " Me Me CH966 " " " " OMe Cl CH967 " " " Me Me OMe N968 " " " " OMe OMe CH969 Me ##STR19## CO.sub.2 -i-Pr H OMe OMe CH970 " " " " " " N971 " " " " H Me N972 " " " " OMe Cl CH973 " " " " Me Me CH974 " " " " SMe NEt.sub.2 N975 " " CO.sub.2 -i-Pr Me OMe Me N976 " " " " OMe OMe CH977 Me " CO.sub.2 -Allyl H OMe OMe CH978 Et " CO.sub.2 Me H OMe OMe CH979 " " " H OMe Me N980 " " " " Me Me CH981 " " " " Cl OMe CH982 " " " Me OMe OMe CH983 " " " " OMe Me N984 " " CO.sub.2 Et H OMe OMe CH985 " " " " OMe Me CH986 " " " " Cl OMe CH987 " " " " OMe Me N988 " " " Me OMe OMe CH989 " " " " " Me N990 " " CO.sub.2 -n-Pr H OMe OMe CH991 " " " " OMe Me N992 " " " " OMe Cl CH993 " " " " Me Me CH994 " " " Me OMO OMe CH995 " " " " OMO Me N996 " " CO.sub.2 -i-Pr H OMe OMe CH997 " " " " OMe Me N998 " " " " Me Me CH999 " " " Me OMe Me N1.000 n-Pr " CO.sub.2 Me H OMe OMe CH1.001 " " " " " Cl CH1.002 " " " " Me Me CH1.003 " " " " OMe Me N1.004 " " " Me OMe OMe CH1.005 " " " " OMe Me N1.006 n-Pr " CO.sub.2 Et H " " N1.007 " " " " Cl OMe CH1.008 " " " " Me Me CH1.009 " " CO.sub.2 -n-Pr OMe OMe CH1.010 i-Pr " CO.sub.2 Me H OMe OMe CH1.011 " " " " OMe Me N1.012 " " " " Me Me CH1.013 " " " " Cl OMe N1.014 " " " Me OMe Me N1.015 " " " " " OMe CH1.016 Allyl " CO.sub.2 Me H OMe OMe CH1.017 " " " " " Cl CH1.018 " " " " Me Me CH1.019 " " " " OMe Me N1.020 " " CO.sub.2 Et H OMe OMe CH1.021 " " CO.sub.2 -n-Pr " " " CH1.022 " " CO.sub.2 -i-Pr " " " CH1.023 Me COPh CO.sub.2 Me H OMe OMe CH1.024 " " " " " OMe N1.025 " " " " " Me N1.026 " " " " OMe " CH1.027 " " " " NMe.sub.2 OCH.sub.2 CF.sub.3 N1.028 " " " " Me Me CH1.029 " " " " " " N1.030 " " " " Cl OMO CH1.031 " " " Me OMe OMe CH1.032 " " " " " Me N1.033 " " CO.sub.2 Et H OMe OMe CH1.034 " " " " " Cl CH1.035 " " " " Me Me CH1.036 " " " " OMe Me N1.037 " " " " NMe.sub.2 OCH.sub.2 CF.sub.3 N1.038 " " " Me OMe OMe CH1.039 " " " " OMe Me N1.040 " " CO.sub.2 -n-Pr H OMe OMe CH1.041 " " " " " " N1.042 " " " " OMe Me N1.043 " " " " Me Me CH1.044 " " " " OMe Cl CH1.045 " " " Me Me OMe N1.046 " " " " OMe OMO CH1.047 Me COPh CO.sub.2 -i-Pr OMe OMe OMe CH1.048 " " " " " " N1.049 " " " " OMe Me N1.050 " " " " OMe Cl CH1.051 " " " " Me Me CH1.052 " " " " SMe NEt.sub.2 N1.053 " " CO.sub.2 -i-Pr Me OMe Me N1.054 " " " " OMe OMe CH1.055 Me " CO.sub.2 -Allyl H OMe OMe CH1.056 Et " CO.sub.2 Me H OMe OMe CH1.057 " " " H OMe Me N1.058 " " " " Me Me CH1.059 " " " " Cl OMe CH1.060 " " " Me OMe OMe CH1.061 " " " " OMe Me N1.062 " " CO.sub.2 Et H OMe OMe CH1.063 " " " " OMe Me CH1.064 " " " " Cl OMe CH1.065 " " " " OMe Me N1.066 " " " Me OMe OMe CH1.067 " " " " " Me N1.068 " " CO.sub.2 -n-Pr H OMe OMe CH1.069 " " " " OMe Me N1.070 " " " " OMe Cl CH1.071 " " " " Me Me CH1.072 " " " Me OMe OMe CH1.073 " " " " OMe Me N1.074 " " CO.sub.2 -i-Pr H OMe OMe CH1.075 " " " " OMe Me N1.076 " " " Me OMe Me N1.077 n-Pr COPh CO.sub.2 Me H OMe OMO CH1.078 " " " " " Cl CH1.079 " " " " Me Me CH1.080 " " " " OMe Me N1.081 " " " Me OMe OMe CH1.082 " " " " OMe Me N1.083 n-Pr " CO.sub.2 Et H " " N1.084 " " " " " OMe CH1.085 " " " " Me Me CH1.086 " " CO.sub.2 -n-Pr " OMe OMe CH1.087 i-Pr " CO.sub.2 Me H OMe OMe CH1.088 " " " " OMe Me N1.089 " " " " Me Me CH1.090 " " " " Cl OMe N1.091 " " " Me OMe Me N1.092 " " " " " OMe CH1.093 Allyl " CO.sub.2 Me H OMe OMe CH1.094 " " " " " Cl CH1.095 " " " " Me Me CH1.096 " " " " OMe Me N1.097 " " CO.sub.2 Et H OMe OMe CH1.098 " " CO.sub.2 -n-Pr H OMe OMe CH1.099 " " CO.sub.2 -i-Pr " " " CH1.100 Me ##STR20## CO.sub.2 Me H OMe OMe CH1.101 " " " " " OMe N1.102 " " " " " Me N1.103 " " " " " " CH1.104 " " " " NMe.sub.2 OCH.sub.2 CF.sub.3 N1.105 " " " " Me Me CH1.106 " " " " " " N1.107 " " " " Cl OMe CH1.108 " " " Me OMe OMe CH1.109 " " " " " Me N1.110 " " CO.sub.2 -El H OMe OMe CH1.111 " " " " " Cl CH1.112 " " " " Me Me CH1.113 " " " " OMe Me N1.114 " " " " NMe.sub.2 OCH.sub.2 CF.sub.3 N1.115 " " " Me OMe OMe CH1.116 " " " " OMe Me N1.117 " " CO.sub.2 -n-Pr H OMe OMe CH1.118 " " " " " " N1.119 " " " " OMe Me N1.120 " " " " Me Me CH1.121 " " " " OMe Cl CH1.122 " " " Me Me OMe N1.123 " " " " OMe OMe CH1.124 Me " CO.sub.2 -i-PT H OMe OMe CH1.125 " " " " " " N1.126 " " " " H Me N1.127 " " " " OMe Cl CH1.128 " " " " Me Me CH1.129 " " " " SMe NEt.sub.2 N1.130 " " CO.sub.2 -i-Pr Me OMe Me N1.131 " " " " OMe OMe CH1.132 Me " CO.sub.2 -Allyl H OMe OMO CH1.133 Et " CO.sub.2 Me H OMe OMe CH1.134 " " " H OMe Me N1.135 " " " " Me Me CH1.136 " " " " Cl OMe CH1.137 " " " Me OMe OMe CH1.138 " " " " OMe Me N1.139 " " CO.sub.2 Et H OMe OMe CH1.140 " " " " OMe Me CH1.141 " " " " Cl OMe CH1.142 " " " " OMe Me N1.143 " " " Me OMe OMe CH1.144 " " " " " Me N1.145 " " CO.sub.2 -n-Pr H OMe OMe CH1.146 " " " " OMe Me N1.147 " " " " OMe Cl CH1.148 " " " " Me Me CH1.149 " " " Me OMe OMe CH1.150 " " " Me OMe Me N1.151 " " CO.sub.2 -i-Pr H OMe OMS CH1.152 " " " " OMe Me N1.153 " " " " Me Me CH1.154 " " " Me OMe Me N1.155 n-Pr ##STR21## CO.sub.2 Me H OMe OMe CH1.156 " " " " " Cl CH1.157 " " " " Me Me cm1.158 " " " " OMe Me N1.159 " " " Me OMe OMe CH1.160 " " " " OMe Me N1.161 n-Pr " CO.sub.2 Et H OMe Me N1.162 " " " " " OMe CH1.163 " " " " Me Me CH1.164 " " CO.sub.2 -n-Pr " OMe OMe CH1.165 i-Pr " CO.sub.2 Me H OMe OMe CH1.166 " " " " OMe Me N1.167 " " " " Me Me CH1.168 " " " " Cl OMe N1.169 " " " Me OMe Me N1.170 " " " " " OMe CH1.171 Allyl " CO.sub.2 Me H OMe OMe CH1.172 " " " " " Cl CH1.173 " " " " Me Me CH1.174 " " " " OMe Me N1.175 " " CO.sub.2 -Et H OMe OMe CH1.176 " " CO.sub.2 -n-Pr " OMe OMe CH1.177 " " CO.sub.2 -i-pr H OMe OMe CH1.178 Me COOMe CO.sub.2 -M8 H OMe OMS CH 128.degree. C.1.179 " " " " " OMe N1.180 " " " " " Me N s. Bsp. o)1.181 " " " " " " CH 89-1011.182 " " " " NM3.sub.2 OCH.sub.2 CF.sub.3 N1.183 " " " " Me Me CH s. Bsp. m)1.184 " " " " " " N1.185 " " " " Cl OMe CH s. Bsp. n)1.186 " " " Me OMe OMe CH 150-1541.187 " " " " " Me N1.188 " " CO.sub.2 Et H OMe OMe CH1.189 " " " " " Cl CH1.190 " " " " Me Me CH1.191 " " " " OMe Me N1.192 " " " " NMe.sub.2 OCH.sub.2 CF.sub.3 N1.193 " " " Me OMe OMe CH1.194 " " " " OMe Me N1.195 " " CO.sub.2 -n-Pr H OMe OMe CH1.196 " " " " " " N1.197 " " " " OMe Me N1.198 " " " " Me Me CH1.199 " " " " OMe Cl CH1.200 " " " Me Me OMe N1.201 " " " " OMe OMe CH1.202 Me COOMe CO.sub.2 -i-Pr H OMe OMe CH1.203 " " " " " " N1.204 " " " " OMe Me N1.205 " " " " OMe Cl CH1.206 " " " " Me Me CH1.207 " " " " SMe NEt.sub.2 N1.208 " " CO.sub.2 -i-Pr Me OMe Me N1.209 " " " " OMe OMe CH1.210 Me " CO.sub.2 -Allyl H OMe OMe CH1.211 Et " CO.sub.2 Me H OMe OMe CH1.212 " " " H OMe Me N1.213 " " " " Me Me CH1.214 " " " " Cl OMS CH1.215 " " " Me OMe OMe CH1.216 " " " " OMe Me N1.217 " " CO.sub. 2 Et H OMe OMe CH1.218 " " " " OMe Me CH1.219 " " " " Cl OMe CH1.220 " " " " OMe Me N1.221 " " " Me OMe OMe CH1.222 " " " " " Me N1.223 " " CO.sub.2 -n-Pr H OMe OMe CH1.224 " " " " OMe Me N1.225 " " " " OMe Cl CH1.226 " " " " Me Me CH1.227 " " " Me OMe OMe CH1.228 " " " " OMe Me N1.229 " " CO.sub.2 -i-Pr H OMe OMe CH1.230 " " " " OMe Me N1.231 " " " " Me Me CH1.232 " " " Me OMe Me N1.233 n-Pr COOMe CO.sub.2 Me H OMe OMe CH1.234 " " " " " Cl CH1.235 " " " " Me Me CH1.236 " " " " OMe Me N1.237 " " " Me OMe OMe CH1.238 " " " " OMe Me N1.239 n-Pr " CO.sub.2 Et H OMe Me N1.240 " " " " " OMe CH1.241 " " " " Me Me CH1.242 " " CO.sub.2 -n-Pr " OMe OMe CH1.243 i-Pr " CO.sub.2 Me H OMe OMe CH1.244 " " " " OMe Me N1.245 " " " " Me Me CH1.246 " " " " Cl OMe N1.247 " " " Me OMe Me N1.248 " " " " " OMe CH1.249 Allyl " CO.sub.2 Me H OMe OMe CH1.250 " " " " " Cl CH1.251 " " " " Me Me CH1.252 " " " " OMe Me N1.253 " " CO.sub.2 Et H OMe OMe CH1.254 " " CO.sub.2 -n-Pr " " " "1.255 " " CO.sub.2 -i-Pr " " " CH1.256 Me COOEt CO.sub.2 Me H OMe OMe CH1.257 " " " " " OMe N1.258 " " " " " Me N1.259 " " " " " " CH1.260 " " " " NMe.sub.2 OCH.sub.2 CF.sub.3 N1.261 " " " " Me Me CH1.262 " " " " " " N1.263 " " " " Cl OMe CH1.264 " " " Me OMe OMe CH1.265 " " " " " Me N1.266 " " CO.sub.2 Et H OMe OMe CH1.267 " " " " " Cl CH1.268 " " " " Me Me CH1.269 " " " " OMe Me N1.270 " " " " NMe.sub.2 OCH.sub.2 CF.sub.3 N1.271 " " " Me OMe OMe CH1.272 " " " " OMe Me N1.273 " " CO.sub.2 -n-Pr H OMe OMe CH1.274 " " " " " " N1.275 " " " " OMe Me N1.276 " " " " Me Me CH1.277 " " " " OMe Cl CH1.278 " " " Me Me OMe N1.279 " " " " OMe OMe CH1.280 Me COOEt CO.sub.2 -i-Pr H OMe OMe CH1.281 " " " " " " N1.282 " " " " OMe Me N1.283 " " " " OMe Cl CH1.284 " " " " Me Me CH1.285 " " " " SMe NEt.sub.2 N1.286 " " CO.sub.2 -i-Pr Me OMe Me N1.287 " " " " OMe OMe CH1.288 Me " CO.sub.2 -Allyl H OMe OMe CH1.289 Et " CO.sub.2 Me H OMe OMe CH1.290 " " " H OMe Me N1.291 " " " " Me Me CH1.292 " " " " Cl OMe CH1.293 " " " Me OMe OMe CH1.294 " " " " OMe Me N1.295 " " CO.sub.2 Et H OMe OMe CH1.296 " " " " OMe Me CH1.297 " " " " Cl OMe CH1.298 " " " " OMe Me N1.299 " " " Me OMe OMe CH1.300 " " " " " Me N1.301 " " CO.sub.2 -n-Pr H OMe OMe CH1.302 " " " " OMe Me N1.303 " " " " OMe Cl CH1.304 " " " " Me Me CH1.305 " " " Me OMe OMe CH1.306 " " " " OMe Me N1.307 " " CO.sub.2 -i-Pr H OMe OMe CH1.308 " " " " OMe Me N1.309 " " " " Me Me CH1.310 " " " Me OMe Me N1.311 n-Pr CO.OEt CO.sub.2 Me H OMe OMe CH1.312 " " " " " Cl CH1.313 " " " " Me Me CH1.314 " " " " OMe Me N1.315 " " " Me OMe OMe CH1.316 " " " " OMe Me N1.317 n-Pr " CO.sub.2 Et H " " N1.318 " " " " " OMe CH1.319 " " " " Me Me CH1.320 " " CO.sub.2 -n-Pr " OMe OMe CH1.321 i-Pr " CO.sub.2 Me H OMe OMe CH1.322 " " " " OMe Me N1.323 " " " " Me Me CH1.324 " " " " Cl OMe N1.325 " " " Me OMe Me N1.326 " " " " " OMe CH1.327 Allyl " CO.sub.2 Me H OMe OMe CH1.328 " " " " " Cl CH1.329 " " " " Me Me CH1.330 " " " " OMe Me N1.331 " " CO.sub.2 Et H OMe OMe CH1.332 " " CO.sub.2 -n-Pr H OMe OMe CH1.333 " " CO.sub.2 -i-Pr " " " "1.334 Me COO-i-Pr CO.sub.2 Me H OMe OMe CH1.335 " " " " " OMe N1.336 " " " " " Me N1.337 " " " " " " CH1.338 " " " " NMe.sub.2 OCH.sub.2 CF.sub.3 N1.339 " " " " Me Me CH1.340 " " " " " " N1.341 " " " " Cl OMe CH1.342 " " " Me OMe OMe CH1.343 " " " " " Me N1.344 " " CO.sub.2 Et H OMe OMe CH1.345 " " " " " Cl CH1.346 " " " " Me Me CH1.347 " " " " OMe Me N1.348 " " " " NMe.sub.2 OCH.sub.2 CF.sub.3 N1.349 " " " Me OMe OMe CH1.350 " " " " OMe Me N1.351 " " CO.sub.2 -n-Pr H OMe OMe CH1.352 " " " " " " N1.353 " " " " OMe Me N1.354 " " " " Me Me CH1.355 " " " " OMe Cl CH1.356 " " " Me Me OMe N1.357 " " " " OMe OMe CH1.358 Me COO-i-Pr CO.sub.2 -i-Pr H OMe OMe CH1.359 " " " " " " N1.360 " " " " H Me N1.361 " " " " OMe Cl CH1.362 " " " " Me Me CH1.363 " " " " SMe NEt.sub.2 N1.364 " " CO.sub.2 -i-Pr Me OMe Me N1.365 " " " " OMe OMe CH1.366 Me " CO.sub.2 -Allyl H OMe OMe CH1.367 Et " CO.sub.2 Me H OMe OMe CH1.368 " " " H OMe Me N1.369 " " " " Me Me CH1.370 " " " " Cl OMe CH1.371 " " " Me OMe OMe CH1.372 " " " " OMe Me N1.373 " " CO.sub.2 Et H OMe OMe CH1.374 " " " " OMe Me CH1.375 " " " " Cl OMe CH1.376 " " " " OMe Me N1.377 " " " Me OMe OMe CH1.378 " " " " " Me N1.379 " " CO.sub.2 -n-Pr H OMe OMe CH1.380 " " " " OMe Me N1.381 " " " " OMe Cl CH1.382 " " " " Me Me CH1.383 " " " Me OMe OMe CH1.384 " " " " OMe Me N1.385 " " CO.sub.2 -i-Pr H OMe OMe CH1.386 " " " " OMe Me N1.387 " " " " Me Me CH1.388 " " " Me OMe Me N1.389 n-Pr COO-i-Pr CO.sub.2 Me H OMe OMe CH1.390 " " " " " Cl CH1.391 " " " " Me Me CH1.392 " " " " OMe Me N1.393 " " " Me OMe OMe CH1.394 " " " " OMe Me N1.395 n-Pr " CO.sub.2 Et H " " N1.396 " " " " " OMe CH1.397 " " " " Me Me CH1.398 " " CO.sub.2 -n-Pr " OMe OMe CH1.399 i-Pr " CO.sub.2 Me H OMe OMe CH1.400 " " " " OMe Me N1.401 " " " " Me Me CH1.402 " " " " Cl OMe N1.403 " " " Me OMe Me N1.404 " " " " " OMe CH1.405 Allyl " CO.sub.2 Me H OMe OMe CH1.406 " " " " " Cl CH1.407 " " " " Me Me CH1.408 " " " " OMe Me N1.409 " " CO.sub.2 Et H OMe OMe CH1.410 " " CO.sub.2 -n-Pr " " " CH1.411 " " CO.sub.2 -i-Pr " " " CH1.412 Me COO-n-Pr CO.sub.2 Me H OMe OMe CH1.413 " " " " " OMe N1.414 " " " " " Me N1.415 " " " " " " CH1.416 " " " " NMe.sub.2 OCH.sub.2 CF.sub.3 N1.417 " " " " Me Me CH1.418 " " " " " " N1.419 " " " " Cl OMe CH1.420 " " " Me OMe OMe CH1.421 " " " " " Me N1.422 " " CO.sub.2 Et H OMe OMe CH1.423 " " " " " Cl CH1.424 " " " " Me Me CH1.425 " " " " OMe Me N1.426 " " " " NMe.sub.2 OCH.sub.2 CF.sub.3 N1.427 " " " Me OMe OMe CH1.428 " " " " OMe Me N1.429 " " CO.sub.2 -n-Pr H OMe OMe CH1.430 " " " " " " N1.431 " " " " OMe Me N1.432 " " " " Me Me CH1.433 " " " " OMe Cl CH1.434 " " " Me Me OMe N1.435 " " " " OMe OMe CH1.436 Me COO-n-Pr CO.sub.2 -i-Pr H OMe OMe CH1.437 " " " " " " N1.438 " " " " OMe Me N1.439 " " " " OMe Cl CH1.440 " " " " Me Me CH1.441 " " " " SMe NEt.sub.2 N1.442 " " CO.sub.2 -i-Pr Me OMe Me N1.443 " " " " OMe OMe CH1.444 Me " CO.sub.2 -Allyi H OMe OMe CH1.445 Et " CO.sub.2 Me H OMe OMe CH1.446 " " " H OMe Me N1.447 " " " " Me Me CH1.448 " " " " Cl OMe CH1.449 " " " Me OMe OMe CH1.450 " " " " OMe Me N1.451 " " CO.sub.2 Et H OMe OMe CH1.452 " " " " OMe Me CH1.453 " " " " Cl OMe CH1.454 " " " " OMe Me N1.455 " " " Me OMe OMe CH1.456 " " " " " Me N1.457 " " CO.sub.2 -n-Pr H OMe OMe CH1.458 " " " " OMe Me N1.459 " " " " OMe Cl CH1.460 " " " " Me Me CH1.461 " " " Me OMe OMe CH1.462 " " " " OMe Me N1.463 " " CO.sub.2 -i-Pr H OMe OMe CH1.464 " " " " OMe Me N1.465 " " " " Me Me CH1.466 " " " Me OMe Me N1.467 n-Pr COO-n-Pr CO.sub.2 Me H OMe OMe CH1.468 " " " " " Cl CH1.469 " " " " Me Me CH1.470 " " " " OMe Me N1.471 " " " Me OMe OMe CH1.472 " " " " OMe Me N1.473 n-Pr " CO.sub. 2 Et H " " N1.474 " " " " " OMe CH1.475 " " " " Me Me CH1.476 " " CO.sub.2 -n-Pr " OMe OMe CH1.477 i-Pr " CO.sub.2 Me H OMe OMe CH1.478 " " " " OMe Me N1.479 " " " " Me Me CH1.480 " " " " Cl OMe N1.481 " " " Me OMe Me N1.482 " " " " " OMe CH1.483 Allyl " CO.sub.2 Me H OMe OMe CH1.484 " " " " " Cl CH1.485 " " " " Me Me CH1.486 " " " " OMe Me N1.487 " " CO.sub.2 Et H OMe OMe CH1.488 " " CO.sub.2 -n-Pr " " " CH1.489 " " CO.sub.2 -i-Pr " " " CH1.490 Me COO-allyl CO.sub.2 Me H OMe OMe CH1.491 " " " " " OMe N1.492 " " " " " Me N1.493 " " " " " " CH1.494 " " " " NMe.sub.2 OCH.sub.2 CF.sub.3 N1.495 " " " " Me Me CH1.496 " " " " " " N1.497 " " " " Cl OMe CH1.498 " " " Me OMe OMe CH1.499 " " " " " Me N1.500 " " CO.sub.2 Et H OMe OMe CH1.501 " " " " " Cl CH1.502 " " " " Me Me CH1.503 " " " " OMe Me N1.504 " " " " NMe.sub.2 OCH.sub.2 CF.sub.3 N1.505 " " " Me OMe OMe CH1.506 " " " " OMe Me N1.507 " " CO.sub.2 -n-Pr H OMe OMe CH1.508 " " " " " " N1.509 " " " " OMe Me N1.510 " " " " Me Me CH1.511 " " " " OMe Cl CH1.512 " " " Me Me OMe N1.513 " " " " OMe OMe CH1.514 Me COO-allyl CO.sub.2 -i-Pr H OMe OMe CH1.515 " " " " " " N1.516 " " " " H Me N1.517 " " " " OMe Cl CH1.518 " " " " Me Me CH1.519 " " " " SMe NEt.sub.2 N1.520 " " CO.sub.2 -i-Pr Me OMe Me N1.521 " " " " OMe OMe CH1.522 Me " CO.sub.2 -Allyl H OMe OMe CH1.523 Et " CO.sub.2 Me H OMe OMe CH1.524 " " " H OMe Me N1.525 " " " " Me Me CH1.526 " " " " Cl OMe CH1.527 " " " Me OMe OMe CH1.528 " " " " OMe Me N1.529 " " CO.sub.2 Et H OMe OMe CH1.530 " " " " OMG Me CH1.531 " " " " Cl OMe CH1.532 " " " " OMe Me N1.533 " " " Me OMe OMe CH1.534 " " " " " Me N1.535 " " CO.sub.2 -n-Pr H OMe OMe CH1.536 " " " " OMe Me N1.537 " " " " OMe Cl CH1.538 " " " " Me Me CH1.539 " " " Me OMe OMe CH1.540 " " " " OMe Me N1.541 " " CO.sub.2 -i-Pr H OMe OMe CH1.542 " " " " OMe Me N1.543 " " " " Me Me CH1.544 " " " Me OMe Me N1.545 n-Pr COO-allyl CO.sub.2 Me H OMe OMe CH1.546 " " " " " Cl CH1.547 " " " " Me Me CH1.548 " " " " OMe Me N1.549 " " " Me OMe OMe CH1.550 " " " " OMe Me N1.551 n-Pr " CO.sub.2 Et H " " N1.552 " " " " " OMe CH1.553 " " " " Me Me CH1.554 " " CO.sub.2 -n-Pr " OMe OMe CH1.555 i-Pr " CO.sub.2 Me H OMe OMe CH1.556 " " " " OMe Me N1.557 " " " " Me Me CH1.558 " " " " Cl OMe N1.559 " " " Me OMe Me N1.560 " " " " " OMe CH1.561 Allyl " CO.sub.2 Me H OMe OMe CH1.562 " " " " " Cl CH1.563 " " " " Me Me CH1.564 " " " " OMe Me N1.565 " " CO.sub.2 Et H OMe OMe CH1.565 " " CO.sub.2 -n-Pr " " " CH1.567 " " CO.sub.2 -i-Pr " " " CH1.568 Me CONHEt CO.sub.2 Me H OMe OMe CH1.569 " " " " " OMe N1.570 " " " " " Me N1.571 " " " " " " CH1.572 " " " " NMe.sub.2 OCH.sub.2 CF.sub.3 N1.573 " " " " Me Me CH1.574 " " " " " " N1.575 " " " " Cl OMe CH1.576 " " " Me OMe OMe CH1.577 " " " " " Me N1.578 " " CO.sub.2 Et H OMe OMe CH1.579 " " " " " Cl CH1.580 " " " " Me Me CH1.581 " " " " OMe Me N1.582 " " " " NMe.sub.2 OCH.sub.2 CF.sub.3 N1.583 " " " Me OMe OMe CH1.584 " " " " OMe Me N1.585 " " CO.sub.2 -n-Pr H OMe OMe CH1.586 " " " " " " N1.587 " " " " OMe Me N1.588 " " " " Me Me CH1.589 " " " " OMe Cl CH1.590 " " " Me Me OMe N1.591 " " " " OMe OMe CH1.592 Me CO NHEt CO.sub.2 -i-Pr H OMe OMe CH1.593 " " " " " " N1.594 " " " " OMe Me N1.595 " " " " OMe Cl CH1.596 " " " " Me Me CH1.597 " " " " SMe NEt.sub.2 N1.598 " " CO.sub.2 -i-Pr Me OMe Me N1.599 " " " " OMe OMe CH1.600 Me " CO.sub.2 -Allyl H OMe OMe CH1.601 Et " CO.sub.2 Me H OMe OMe CH1.602 " " " H OMe Me N1.603 " " " " Me Me CH1.604 " " " " Cl OMe CH1.605 " " " Me OMe OMe CH1.606 " " " " OMe Me N1.607 " " CO.sub.2 Et H OMe OMe CH1.608 " " " " OMe Me CH1.609 " " " " Cl OMe CH1.610 " " " " OMe Me N1.611 " " " Me OMe OMe CH1.612 " " " " " Me N1.613 " " CO.sub.2 -n-Pr H OMe OMe CH1.614 " " " " OMS Me N1.615 " " " " OMe Cl CH1.616 " " " " Me Me CH1.617 " " " Me OMe OMe CH1.618 " " " " OMe Me N1.619 " " CO.sub.2 -i-Pr H OMe OMe CH1.620 " " " " OMe Me N1.621 " " " " Me Me CH1.622 " " " Me OMe Me N1.623 n-Pr CONHEt CO.sub.2 Me H OMe OMe CH1.624 " " " " " Cl CH1.625 " " " " Me Me CH1.626 " " " " OMe Me N1.627 " " " Me OMe OMe CH1.628 " " " " OMe Me N1.629 n-Pr " CO.sub.2 Et H " " N1.630 " " " " " OMe CH1.631 " " " " Me Me CH1.632 " " CO.sub.2 -n-Pr " OMe OMe CH1.633 i-Pr " CO.sub.2 Me H OMe OMe CH1.634 " " " " OMe Me N1.635 " " " " Me Me CH1.636 " " " " Cl OMe N1.637 " " " Me OMe Me N1.638 " " " " " OMe CH1.639 Allyl " CO.sub.2 Me H OMe OMe CH1.640 " " " " " Cl CH1.641 " " " " Me Me CH1.642 " " " " OMe Me N1.643 " " CO.sub.2 Et H OMe OMe CH1.644 " " CO.sub.2 -n-Pr " " " CH1.645 " " CO.sub.2 -i-Pr " " " CH1.646 Me CONHPr CO.sub.2 Me H " " CH1.647 " " " " " OMe N1.648 " " " " " Me N1.649 " " " " " " CH1.650 " " " " NMe.sub.2 OCH.sub.2 CF.sub.3 N1.651 " " " " Me Me CH1.652 " " " " " " N1.653 " " " " Cl OMS CH1.654 " " " Me OMe OMe CH1.655 " " " " " Me N1.656 " " CO.sub.2 Et H OMe OMe CH1.657 " " " " " Cl CH1.658 " " " " Me Me CH1.659 " " " " OMe Me N1.660 " " " " NMe.sub.2 OCH.sub.2 CF.sub.3 N1.661 " " " Me OMe OMe CH1.662 " " " " OMe Me N1.663 " " CO.sub.2 -n-Pr H OMe OMe CH1.664 " " " " " " N1.665 " " " " OMe Me N1.666 " " " " Me Me CH1.667 " " " " OMe Cl CH1.668 " " " Me Me OMe N1.669 " " " " OMe OMe CH1.670 Me CONHPR CO.sub.2 -i-Pr H OMe OMe CH1.671 " " " " " " N1.672 " " " " OMe Me N1.673 " " " " OMe Cl CH1.674 " " " " Me Me CH1.675 " " " " SMe NEt.sub.2 N1.676 " " CO.sub.2 -i-Pr Me OMe Me N1.677 " " " " OMB OMe CH1.678 Me " CO.sub.2 -Allyl H OMe OMe CH1.679 Et " CO.sub.2 Me H OMe OMe CH1.680 " " " H OMe Me N1.681 " " " " Me Me CH1.682 " " " " Cl OMe CH1.683 " " " Me OMe OMe CH1.684 " " " " OMe Me N1.685 " " CO.sub.2 Et H OMe OMe CH1.686 " " " " OMe Me CH1.687 " " " " Cl OMe CH1.688 " " " " OMe Me N1.689 " " " Me OMe OMe CH1.690 " " " " " Me N1.691 " " CO.sub.2 -n-Pr H OMe OMe CH1.692 " " " " OMe Me N1.693 " " " " OMe Cl CH1.694 " " " " Me Me CH1.695 " " " Me OMe OMe CH1.696 " " " " OMe Me N1.697 " " CO.sub.2 -i-Pr H OMe OMe CH1.698 " " " " OMe Me N1.699 " " " " Me Me CH1.700 " " " Me OMe Me N1.701 n-Pr " CO.sub.2 Me H OMe OMe CH1.702 " " " " " Cl CH1.703 " " " " Me Me CH1.704 " " " " OMe Me N1.705 " " " Me OMe OMe CH1.706 " " " " OMe Me N1.707 n-Pr " CO.sub.2 Et H " " N1.708 " " " " " OMe CH1.709 " " " " Me Me CH1.710 " " CO.sub.2 -n-Pr " OMe OMe CH1.711 i-Pr " CO.sub.2 Me H OMe OMe CH1.712 " " " " OMe Me N1.713 " " " " Me Me CH1.714 " " " " Cl OMe N1.715 " " " Me OMe Me N1.716 " " " " " OMe CH1.717 Allyl " CO.sub.2 Me H OMe OMe CH1.718 " " " " " Cl CH1.719 " " " " Me Me CH1.720 " " " " OMe Me N1.721 " " CO.sub.2 Et H OMe OMe CH__________________________________________________________________________
__________________________________________________________________________No. R.sup.1 R.sup.2 R.sup.3 R.sup.4 X Y Z m.p.__________________________________________________________________________1.722 " " CO.sub.2 -n-Pr " " " CH1.723 " " CO.sub.2 -i-Pr " " " CH1.724 Me CONH-allyl CO.sub.2Me H OMe OMe CH1.725 " " " " " OMe N1.726 " " " " " Me N1.727 " " " " " " CH1.728 " " " " NMe.sub.2 OCH.sub.2 CF.sub.3 N1.729 " " " " Me Me CH1.730 " " " " " " N1.731 " " " " Cl OMe CH1.732 " " " Me OMe OMe CH1.733 " " " " " Me N1.734 " " CO.sub.2Et H OMe OMe CH1.735 " " " " " Cl CH1.736 " " " " Me Me CH1.737 " " " " OMe Me N1.738 " " " " NMe.sub.2 OCH.sub.2 CF.sub.3 N1.739 " " " Me OMe OMe CH1.740 " " " " OMe Me N1.741 " " CO.sub.2 -n-Pr H OMe OMe CH1.742 " " " " " " N1.743 " " " " OMe Me N1.744 " " " " Me Me CH1.745 " " " " OMe Cl CH1.746 " " " Me Me OMe N1.747 " " " " OMe OMe CH1.748 Me CONH-allyl CO.sub.2 -i-Pr H OMe OMe CH1.749 " " " " " " N1.750 " " " " OMe Me N1.751 " " " " OMe Cl CH1.752 " " " " Me Me CH1.753 " " " " SMe NEt.sub.2 N1.754 " " CO.sub.2 -i-Pr Me OMe Me N1.755 " " " " OMe OMe CH1.756 Me " CO.sub.2 -Allyl H OMe OMe CH1.757 Et " CO.sub.2Me H OMe OMe CH1.758 " " " H OMe Me N1.759 " " " " Me Me CH1.760 " " " " Cl OMe CH1.761 " " " Me OMe OMe CH1.762 " " " " OMe Me N1.763 " " CO.sub.2Et H OMe OMe CH1.764 " " " " OMe Me CH1.765 " " " " Cl OMe CH1.766 " " " " OMe Me N1.767 " " " Me OMe OMe CH1.768 " " " " " Me N1.769 " " CO.sub.2 -n-Pr H OMe OMe CH1.770 " " " " OMe Me N1.771 " " " " OMe Cl CH1.772 " " " " Me Me CH1.773 " " " Me OMe OMe CH1.774 " " " " OMe Me N1.775 " " CO.sub.2 -i-Pr H OMe OMe CH1.776 " " " " OMe Me N1.777 " " " " Me Me CH1.778 " " " Me OMe Me N1.779 n-Pr CONH-allyl CO.sub.2Me H OMe OMe CH1.780 " " " " " Cl CH1.781 " " " " Me Me CH1.782 " " " " OMe Me N1.783 " " " Me OMe OMe CH1.784 " " " " OMe Me N1.785 n-Pr " CO.sub.2Et H OMe Me N1.786 " " " " " OMe CH1.787 " " " " Me Me CH1.788 " " CO.sub.2 -n-Pr " OMe OMe CH1.789 i-Pr " CO.sub.2Me H OMe OMe CH1.790 " " " " OMe Me N1.791 " " " " Me Me CH1.792 " " " " Cl OMe N1.793 " " " Me OMe Me N1.794 " " " " " OMe CH1.795 Allyl " CO.sub.2Me H OMe OMe CH1.796 " " " " " Cl CH1.797 " " " " Me Me CH1.798 " " " " OMe Me N1.799 " " CO.sub.2Et H OMe OMe CH1.800 " " CO.sub.2 -n-Pr " " " "1.801 " " CO.sub.2 -i-Pr " " " "1.802 Me CSNHMe CO.sub.2Me H OMe OMe CH1.803 " " " " " OMe N1.804 " " " " " Me N1.805 " " " " " " CH1.806 " " " " NMe.sub.2 OCH.sub.2 CF.sub.3 N1.807 " " " " Me Me CH1.808 " " " " " " N1.809 " " " " Cl OMe CH1.810 " " " Me OMe OMe CH1.811 " " " " " Me N1.812 " " CO.sub.2Et H OMe OMe CH1.813 " " " " " Cl CH1.814 " " " " Me Me CH1.815 " " " " OMe Me N1.816 " " " " NMe.sub.2 OCH.sub.2 CF.sub.3 N1.817 " " " Me OMe OMe CH1.818 " " " " OMe Me N1.819 " " CO.sub.2 -n-Pr H OMe OMe CH1.820 " " " " " " N1.821 " " " " OMe Me N1.822 " " " " Me Me CH1.823 " " " " OMe Cl CH1.824 " " " Me Me OMe N1.825 " " " " OMe OMe CH1.826 Me CSNHMe CO.sub.2 -i-Pr H OMe OMe CH1.827 " " " " " " N1.828 " " " " OMe Me N1.829 " " " " OMe Cl CH1.830 " " " " Me Me CH1.831 " " " " SMe NEt.sub.2 N1.832 " " CO.sub.2 -i-Pr Me OMe Me N1.833 " " " " OMe OMe CH1.834 Me " CO.sub.2 -Allyl H OMe OMe CH1.835 Et " CO.sub.2Me H OMe OMe CH1.836 " " " H OMe Me N1.837 " " " " Me Me CH1.838 " " " " Cl OMe CH1.839 " " " Me OMe OMe CH1.840 " " " " OMe Me N1.841 " " CO.sub.2Et H OMe OMe CH1.842 " " " " OMe Me CH1.843 " " " " Cl OMe CH1.844 " " " " OMe Me N1.845 " " " Me OMe OMe CH1.846 " " " " " Me N1.847 " " CO.sub.2 -n-Pr H OMe OMe CH1.848 " " " " OMe Me N1.849 " " " " OMe Cl CH1.850 " " " " Me Me CH1.851 " " " Me OMe OMe CH1.852 " " " " OMe Me N1.853 " " CO.sub.2 -i-Pr H OMe OMe CH1.854 " " " " OMe Me N1.855 " " " " Me Me CH1.856 " " " Me OMe Me N1.857 n-Pr CSNHMe CO.sub.2Me H OMe OMe CH1.858 " " " " " Cl CH1.859 " " " " Me Me CH1.860 " " " " OMe Me N1.861 " " " Me OMe OMe CH1.862 " " " " OMe Me N1.863 n-Pr " CO.sub.2Et H " " N1.864 " " " " " OMe CH1.865 " " " " Me Me CH1.866 " " CO.sub.2 -n-Pr " OMe OMe CH1.867 i-Pr " CO.sub.2Me H OMe OMe CH1.868 " " " " OMe Me N1.869 " " " " Me Me CH1.870 " " " " Cl OMe N1.871 " " " Me OMe Me N1.872 " " " " " OMe CH1.873 Allyl " CO.sub.2Me H OMe OMe CH1.874 " " " " " Cl CH1.875 " " " " Me Me CH1.876 " " " " OMe Me N1.877 " " CO.sub.2Et H OMe OMe CH1.878 " " CO.sub.2 -n-Pr H OMe OMe CH1.879 " " CO.sub.2 -i-Pr " " " "1.880 Me CSNHEt CO.sub.2Me H OMe OMe CH1.881 " " " " " OMe N1.882 " " " " " Me N1.883 " " " " " " CH1.884 " " " " NMe.sub.2 OCH.sub.2 CF.sub.3 N1.885 " " " " Me Me CH1.886 " " " " " " N1.887 " " " " Cl OMe CH1.888 " " " Me OMe OMe CH1.889 " " " " " Me N1.890 " " CO.sub.2Et H OMe OMe CH1.891 " " " " " Cl CH1.892 " " " " Me Me CH1.893 " " " " OMe Me N1.894 " " " " NMe.sub.2 OCH.sub.2 CF.sub.3 N1.895 " " " Me OMe OMe CH1.896 " " " " OMe Me N1.897 " " CO.sub.2 -n-Pr H OMe OMe CH1.898 " " " " " " N1.899 " " " " OMe Me N1.900 " " " " Me Me CH1.901 " " " " OMe Cl CH1.902 " " " Me Me OMe N1.903 " " " " OMe OMe CH1.904 Me CSNHEt CO.sub.2 -i-Pr H OMe OMe CH1.905 " " " " " " N1.906 " " " " OMe Me N1.907 " " " " OMe Cl CH1.908 " " " " Me Me CH1.909 " " " " SMe NEt.sub.2 N1.910 " " CO.sub.2 -i-Pr Me OMe Me N1.911 " " " " OMe OMe CH1.912 Me " CO.sub.2 -Allyl H OMe OMe CH1.913 Et " CO.sub.2Me H OMe OMe CH1.914 " " " H OMe Me N1.915 " " " " Me Me CH1.916 " " " " Cl OMe CH1.917 " " " Me OMe OMe CH1.918 " " " " OMe Me N1.919 " " CO.sub.2Et H OMe OMe CH1.920 " " " " " Me CH1.921 " " " " Cl OMe CH1.922 " " " " OMe Me N1.923 " " " Me OMe OMe CH1.924 " " " " " Me N1.925 " " CO.sub.2 -n-Pr H OMe OMe CH1.926 " " " " OMe Me N1.927 " " " " OMe Cl CH1.928 " " " " Me Me CH1.929 " " " Me OMe OMe CH1.930 " " " " OMe Me N1.931 " " CO.sub.2 -i-Pr H OMe OMe CH1.932 " " " " OMe Me N1.933 " " " " Me Me CH1.934 " " " Me OMe Me N1.935 n-Pr CSNHEt CO.sub.2Me H OMe OMe CH1.936 " " " " " Cl CH1.937 " " " " Me Me CH1.938 " " " " OMe Me N1.939 " " " Me OMe OMe CH1.940 " " " " OMe Me N1.941 n-Pr " CO.sub.2Et H " " N1.942 " " " " " OMe CH1.943 " " " " Me Me CH1.944 " " CO.sub.2 -n-Pr " OMe OMe CH1.945 i-Pr " CO.sub.2Me H OMe OMe CH1.946 " " " " OMe Me N1.947 " " " " Me Me CH1.948 " " " " Cl OMe N1.949 " " " Me OMe Me N1.950 " " " " " OMe CH1.951 Allyl " CO.sub.2Me H OMe OMe CH1.952 " " " " " Cl CH1.953 " " " " Me Me CH1.954 " " " " OMe Me N1.955 " " CO.sub.2Et H OMe OMe CH1.956 " " CO.sub.2 -n-Pr " " " CH1.957 " " CO.sub.2 -i-Pr " " " CH1.958 Me CSNH-n-Pr CO.sub.2Me H OMe OMe CH1.959 " " " " " OMe N1.960 " " " " " Me N1.961 " " " " " " CH1.962 " " " " NMe.sub.2 OCH.sub.2 CF.sub.3 N1.963 " " " " Me Me CH1.964 " " " " " " N1.965 " " " " Cl OMe CH1.966 " " " Me OMe OMe CH1.967 " " " " " Me N1.968 " " CO.sub.2Et H OMe OMe CH1.969 " " " " " Cl CH1.970 " " " " Me Me CH1.971 " " " " OMe Me N1.972 " " " " NMe.sub.2 OCH.sub.2 CF.sub.3 N1.973 " " " Me OMe OMe CH1.974 " " " " OMe Me N1.975 " " CO.sub.2 -n-Pr H OMe OMe CH1.976 " " " " " " N1.977 " " " " OMe Me N1.978 " " " " Me Me CH1.979 " " " " OMe Cl CH1.980 " " " Me Me OMe N1.981 " " " " OMe OMe CH1.982 Me CSNH-n-Pr CO.sub.2 -i-Pr H OMe OMe CH1.983 " " " " " " N1.984 " " " " OMe Me N1.985 " " " " OMe Cl CH1.986 " " " " Me Me CH1.987 " " " " SMe NEt.sub.2 N1.988 " " CO.sub.2 -i-Pr Me OMe Me N1.989 " " " " OMe OMe CH1.990 Me " CO.sub.2 -Allyl H OMe OMe CH1.991 Et " CO.sub.2Me H OMe OMe CH1.992 " " " H OMe Me N1.993 " " " " Me Me CH1.994 " " " " Cl OMe CH1.995 " " " Me OMe OMe CH1.996 " " " " OMe Me N1.997 " " CO.sub.2Et H OMe OMe CH1.998 " " " " OMe Me CH1.999 " " " " Cl OMe CH2.000 " " " " OMe Me N2.001 " " " Me OMe OMe CH2.002 " " " " " Me N2.003 " " CO.sub.2 -n-Pr H OMe OMe CH2.004 " " " " OMe Me N2.005 " " " " OMe Cl CH2.006 " " " " Me Me CH2.007 " " " Me OMe OMe CH2.008 " " " " OMe Me N2.009 " " CO.sub.2 -i-Pr H OMe OMe CH2.010 " " " " OMe Me N2.011 " " " " Me Me CH2.012 " " " Me OMe Me N2.013 n-Pr CSNH-n-Pr CO.sub.2Me H OMe OMe CH2.014 " " " " " Cl CH2.015 " " " " Me Me CH2.016 " " " " OMe Me N2.017 " " " Me OMe OMe CH2.018 " " " " OMe Me N2.019 n-Pr " CO.sub.2Et H " " N2.020 " " " " " OMe CH2.021 " " " " Me Me CH2.022 " " CO.sub.2 -n-Pr " OMe OMe CH2.023 i-Pr " CO.sub.2Me H " " CH2.024 " " " " " Me N2.025 " " " " Me Me CH2.026 " " " " Cl OMe N2.027 " " " Me OMe Me N2.028 " " " " " OMe CH2.029 Allyl " CO.sub.2Me H OMe OMe CH2.030 " " " " " Cl CH2.031 " " " " Me Me CH2.032 " " " " OMe Me N2.033 " " CO.sub.2Et H OMe OMe CH2.034 " " CO.sub.2 -n-Pr " " " CH2.035 " " CO.sub.2 -i-Pr " " " CH2.036 Me CSNH-i-Pr CO.sub.2Me H OMe OMe CH2.037 " " " " " OMe N2.038 " " " " " Me N2.039 " " " " " " CH2.040 " " " " NMe.sub.2 OCH.sub.2 CF.sub.3 N2.041 " " " " Me Me CH2.042 " " " " " " N2.043 " " " " Cl OMe CH2.044 " " " Me OMe OMe CH2.045 " " " " " Me N2.046 " " CO.sub.2Et H OMe OMe CH2.047 " " " " " Cl CH2.048 " " " " Me Me CH2.049 " " " " OMe Me N2.050 " " " " NMe.sub.2 OCH.sub.2 CF.sub.3 N2.051 " " " Me OMe OMe CH2.052 " " " " OMe Me N2.053 " " CO.sub.2 -n-Pr H OMe OMe CH2.054 " " " " " " N2.055 " " " " OMe Me N2.056 " " " " Me Me CH2.057 " " " " OMe Cl CH2.058 " " " Me Me OMe N2.059 " " " " OMe OMe CH2.060 Me CSNH-i-Pr CO.sub.2 -i-Pr H OMe OMe CH2.061 " " " " " " N2.062 " " " " OMe Me N2.063 " " " " OMe Cl CH2.064 " " " " Me Me CH2.065 " " " " SMe NEt.sub.2 N2.066 " " CO.sub.2 -i-Pr Me OMe Me N2.067 " " " " OMe OMe CH2.068 Me " CO.sub.2 -Allyl H OMe OMe CH2.069 Et " CO.sub.2Me H OMe OMe CH2.070 " " " H OMe Me N2.071 " " " " Me Me CH2.072 " " " " Cl OMe CH2.073 " " " Me OMe OMe CH2.074 " " " " OMe Me N2.075 " " CO.sub.2Et H OMe OMe CH2.076 " " " " OMe Me CH2.077 " " " " Cl OMe CH2.078 " " " " OMe Me N2.079 " " " Me OMe OMe CH2.080 " " " " " Me N2.081 " " CO.sub.2 -n-Pr H OMe OMe CH2.082 " " " " OMe Me N2.083 " " " " OMe Cl CH2.084 " " " " Me Me CH2.085 " " " Me OMe OMe CH2.086 " " " " OMe Me N2.087 " " CO.sub.2 -i-Pr H OMe OMe CH2.088 " " " " OMe Me N2.089 " " " " Me Me CH2.090 " " " Me OMe Me N2.091 n-Pr CSNH-i-Pr CO.sub.2Me H OMe OMe CH2.092 " " " " " Cl CH2.093 " " " " Me Me CH2.094 " " " " OMe Me N2.095 " " " Me OMe OMe CH2.096 " " " " OMe Me N2.097 n-Pr " CO.sub. 2Et H " " N2.098 " " " " " OMe CH2.099 " " " " Me Me CH2.100 " " CO.sub.2 -n-Pr " OMe OMe CH2.101 i-Pr " CO.sub.2Me H OMe OMe CH2.102 " " " " OMe Me N2.103 " " " " Me Me CH2.104 " " " " Cl OMe N2.105 " " " Me OMe Me N2.106 " " " " " OMe CH2.107 Allyl " CO.sub.2Me H OMe OMe CH2.108 " " " " " Cl CH2.109 " " " " Me Me CH2.110 " " " " OMe Me N2.111 " " CO.sub.2Et H OMe OMe CH2.112 " " CO.sub.2 -n-Pr " " " CH2.113 " " CO.sub.2 -i-Pr " " " CH2.114 Me CSNH-allyl CO.sub.2Me H OMe OMe CH2.115 " " " " " OMe N2.116 " " " " " Me N2.117 " " " " " " CH2.118 " " " " NMe.sub.2 OCH.sub.2 CF.sub.3 N2.119 " " " " Me Me CH2.120 " " " " " " N2.121 " " " " Cl OMe CH2.122 " " " Me OMe OMe CH2.123 " " " " " Me N2.124 " " CO.sub.2Et H OMe OMe CH2.125 " " " " " Cl CH2.126 " " " " Me Me CH2.127 " " " " OMe Me N2.128 " " " " NMe.sub.2 OCH.sub.2 CF.sub.3 N2.129 " " " Me OMe OMe CH2.130 " " " " OMe Me N2.131 " " CO.sub.2 -n-Pr H OMe OMe CH2.132 " " " " " " N2.133 " " " " OMe Me N2.134 " " " " Me Me CH2.135 " " " " OMe Cl CH2.136 " " " Me Me OMe N2.137 " " " " OMe OMe CH2.138 Me CSNH-allyl CO.sub.2 -i-Pr H OMe OMe CH2.139 " " " " " " N2.140 " " " " H Me N2.141 " " " " OMe Cl CH2.142 " " " " Me Me CH2.143 " " " " SMe NEt.sub.2 N2.144 " " CO.sub.2 -i-Pr Me OMe Me N2.145 " " " " OMe OMe CH2.146 Me " CO.sub.2 -Allyl H OMe OMe CH2.147 Et " CO.sub.2Me H OMe OMe CH2.148 " " " H OMe Me N2.149 " " " " Me Me CH2.150 " " " " Cl OMe CH2.151 " " " Me OMe OMe CH2.152 " " " " OMe Me N2.153 " " CO.sub.2Et H OMe OMe CH2.154 " " " " OMe Me CH2.155 " " " " Cl OMe CH2.156 " " " " OMe Me N2.157 " " " Me OMe OMe CH2.158 " " " " " Me N2.159 " " CO.sub.2 -n-Pr H OMe OMe CH2.160 " " " " OMe Me N2.161 " " " " OMe Cl CH2.162 " " " " Me Me CH2.163 " " " Me OMe OMe CH2.164 " " " " OMe Me N2.165 " " CO.sub.2 -i-Pr H OMe OMe CH2.166 " " " " OMe Me N2.167 " " " " Me Me CH2.168 " " " Me OMe Me N2.169 n-Pr CSNH-allyl CO.sub.2Me H OMe OMe CH2.170 " " " " " Cl CH2.171 " " " " Me Me CH2.172 " " " " OMe Me N2.173 " " " Me OMe OMe CH2.174 " " " " OMe Me N2.175 n-Pr " CO.sub.2Et H " " N2.176 " " " " " OMe CH2.177 " " " " Me Me CH2.178 " " CO.sub.2 -n-Pr " OMe OMe CH2.179 i-Pr " CO.sub.2Me H OMe OMe CH2.180 " " " " OMe Me N2.181 " " " " Me Me CH2.182 " " " " Cl OMe N2.183 " " " Me OMe Me N2.184 " " " " " OMe CH2.185 Allyl " CO.sub.2Me H OMe OMe CH2.186 " " " " " Cl CH2.187 " " " " Me Me CH2.188 " " " " OMe Me N2.189 " " CO.sub.2Et H OMe OMe CH2.190 " " CO.sub.2 -n-Pr " " " CH2.191 " " CO.sub.2 -i-Pr " " " CH2.192 Me CSNHCO.sub.2 Et CO.sub.2Me H OMe OMe CH 144-145.degree. C.2.193 " " " " " OMe N2.194 " " " " " Me N2.195 " " " " " " CH2.196 " " " " NMe.sub.2 OCH.sub.2 CF.sub.3 N2.197 " " " " Me Me CH2.198 " " " " " " N2.199 " " " " Cl OMe CH2.200 " " " Me OMe OMe CH2.201 " " " " " Me N2.202 " " CO.sub.2Et H OMe OMe CH2.203 " " " " " Cl CH2.204 " " " " Me Me CH2.205 " " " " OMe Me N2.206 " " " " NMe.sub.2 OCH.sub.2 CF.sub.3 N2.207 " " " M OMe OMe CH2.208 " " " " OMe Me N2.209 " " CO.sub.2 -n-Pr H OMe OMe CH2.210 " " " " " " N2.211 " " " " OMe OMe N2.212 " " " " Me Me CH2.213 " " " " OMe Cl CH2.214 " " " Me Me OMe N2.215 " " " " OMe OMe CH2.216 Me CSNHCO.sub.2 Et CO.sub.2 -i-Pr H OMe OMe CH2.217 " " " " " " N2.218 " " " " OMe Me N2.219 " " " " OMe Cl CH2.220 " " " " Me Me CH2.221 " " " " SMe NEt.sub.2 N2.222 " " CO.sub.2 -i-Pr Me OMe Me N2.223 " " " " OMe OMe CH2.224 Me " CO.sub.2 -Allyl H OMe OMe CH2.225 Et " CO.sub.2Me H OMe OMe CH2.226 " " " H OMe Me N2.227 " " " " Me Me CH2.228 " " " " Cl OMe CH2.229 " " " Me OMe OMe CH2.230 " " " " OMe Me N2.231 " " CO.sub.2Et H OMe OMe CH2.232 " " " " OMe Me CH2.233 " " " " Cl OMe CH2.234 " " " " OMe Me N2.235 " " " Me OMe OMe CH2.236 " " " " " Me N2.237 " " CO.sub.2 -n-Pr H OMe OMe CH2.238 " " " " OMe Me N2.239 " " " " OMe Cl CH2.240 " " " " Me Me CH2.241 " " " Me OMe OMe CH2.242 " " " " OMe Me N2.243 " " CO.sub.2 -i-Pr H OMe OMe CH2.244 " " " " OMe Me N2.245 " " " " Me Me CH2.246 " " " Me OMe Me N2.247 n-Pr CSNHCO.sub.2 Et CO.sub.2Me H OMe OMe CH2.248 " " " " " Cl CH2.249 " " " " Me Me CH2.250 " " " " OMe Me N2.251 " " " Me OMe OMe CH2.252 " " " " OMe Me N2.253 n-Pr " CO.sub.2Et H " " N2.254 " " " " " OMe CH2.255 " " " " Me Me CH2.256 " " CO.sub.2 -n-Pr " OMe OMe CH2.257 i-Pr " CO.sub.2Me H OMe OMe CH2.258 " " " " OMe Me N2.259 " " " " Me Me CH2.260 " " " " Cl OMe N2.261 " " " Me OMe Me N2.262 " " " " " OMe CH2.263 Allyl " CO.sub.2Me H OMe OMe CH2.264 " " " " " Cl CH2.265 " " " " Me Me CH2.266 " " " " OMe Me N2.267 " " CO.sub.2Et H OMe OMe CH2.268 " " CO.sub.2 -n-Pr H OMe OMe CH2.269 " " CO.sub.2 -i-Pr " " " CH2.270 Me SO.sub.2 NHMe CO.sub.2Me H OMe OMe CH 117-118.degree. C.2.271 " " " " " OMe N2.272 " " " " " Me N2.273 " " " " " " CH2.274 " " " " NMe.sub.2 OCH.sub.2 CF.sub.3 N2.275 " " " " Me Me CH2.276 " " " " " " N2.277 " " " " Cl OMe CH2.278 " " " Me OMe OMe CH2.279 " " " " " Me N2.280 " " CO.sub.2Et H OMe OMe CH2.281 " " " " " Cl CH2.282 " " " " Me Me CH2.283 " " " " OMe Me N2.284 " " " " NMe.sub.2 OCH.sub.2 CF.sub.3 N2.285 " " " Me OMe OMe CH2.286 " " " " OMe Me N2.287 " " CO.sub.2 -n-Pr H OMe OMe CH2.288 " " " " " " N2.289 " " " " OMe Me N2.290 " " " " Me Me CH2.291 " " " " OMe Cl CH2.292 " " " Me Me OMe N2.293 " " " " OMe OMe CH2.294 Me SO.sub.2NHMe CO.sub.2 -i-Pr H OMe OMe CH2.295 " " " " " " N2.296 " " " " OMe Me N2.297 " " " " Me Me CH2.298 " " " " Me Me CH2.299 " " " " SMe NEt.sub.2 N2.300 " " CO.sub.2 -i-Pr Me OMe Me N2.301 " " " " OMe OMe CH2.302 Me " CO.sub.2 -Allyl H OMe OMe CH2.303 Et " CO.sub.2Me H OMe OMe CH2.304 " " " H OMe Me N2.305 " " " " Me Me CH2.306 " " " " Cl OMe CH2.307 " " " Me OMe OMe CH2.308 " " " " OMe Me N2.309 " " CO.sub.2Et H OMe OMe CH2.310 " " " " OMe Me CH2.311 " " " " Cl OMe CH2.312 " " " " OMe Me N2.313 " " " Me OMe OMe CH2.314 " " " " " Me N2.315 " " CO.sub.2 -n-Pr H OMe OMe CH2.316 " " " " OMe Me N2.317 " " " " OMe Cl CH2.318 " " " " Me Me CH2.319 " " " Me OMe OMe CH2.320 " " " " OMe Me N2.321 " " CO.sub.2 -i-Pr H OMe OMe CH2.322 " " " " OMe Me N2.323 " " " " Me Me CH2.324 " " " Me OMe Me N2.325 n-Pr SO.sub.2 NHMe CO.sub.2Me H OMe OMe CH2.326 " " " " " Cl CH2.327 " " " " Me Me CH2.328 " " " " OMe Me N2.329 " " " Me OMe OMe CH2.330 " " " OMe Me N2.331 n-Pr " CO.sub.2Et H " " N2.332 " " " " " OMe CH2.333 " " " " Me Me CH2.334 " " CO.sub.2 -n-Pr " OMe OMe CH2.335 i-Pr " CO.sub.2Me H OMe OMe CH2.336 " " " " OMe Me N2.337 " " " " Me Me CH2.338 " " " " Cl OMe N2.339 " " " Me OMe Me N2.340 " " " " " OMe CH2.341 Allyl " CO.sub.2Me H OMe OMe CH2.342 " " " " " Cl CH2.343 " " " " Me Me CH2.344 " " " " OMe Me N2.345 " " CO.sub.2Et H OMe OMe CH2.346 " " CO.sub.2 -n-Pr H OMe OMe CH2.347 " " CO.sub.2 -i-Pr " " " CH2.348 Me SO.sub.2 NMe.sub.2 CO.sub.2Me H OMe OMe CH2.349 " " " " " OMe N2.350 " " " " " Me N2.351 " " " " " " CH2.352 " " " " NMe.sub.2 OCH.sub.2 CF.sub.3 N2.353 " " " " Me Me CH2.354 " " " " " " N2.355 " " " " Cl OMe CH2.356 " " " Me OMe OMe CH2.357 " " " " " Me N2.358 " " CO.sub.2 Et H OMe OMe CH2.359 " " " " " Cl CH2.360 " " " " Me Me CH2.361 " " " " OMe Me N2.362 " " " " NMe.sub.2 OCH.sub.2 CF.sub.3 N2.363 " " " Me OMe OMe CH2.364 " " " " OMe Me N2.365 " " CO.sub.2 -n-Pr H OMe OMe CH2.366 " " " " " " N2.367 " " " " OMe Me N2.368 " " " " Me Me CH2.369 " " " " OMe Cl CH2.370 " " " Me Me OMe N2.371 " " " " OMe OMe CH2.372 Me SO.sub.2 NMe.sub.2 CO.sub.2 -i-Pr H OMe OMe CH2.373 " " " " " " N2.374 " " " " OMe Me N2.375 " " " " OMe Cl CH2.376 " " " " Me Me CH2.377 " " " " SMe NEt.sub.2 N2.378 " " CO.sub.2 -i-Pr Me OMe Me N2.379 " " " " OMe OMe CH2.380 Me " CO.sub.2 -Allyl H OMe OMe CH2.381 Et " CO.sub.2Me H OMe OMe CH2.382 " " " H OMe Me N2.383 " " " " Me Me CH2.384 " " " " Cl OMe CH2.385 " " " Me OMe OMe CH2.386 " " " " OMe Me N2.387 " " CO.sub.2Et H OMe OMe CH2.388 " " " " OMe Me CH2.389 " " " " Cl OMe CH2.390 " " " " OMe Me N2.391 " " " Me OMe OMe CH2.392 " " " " " Me N2.393 " " CO.sub.2 -n-Pr H OMe OMe CH2.394 " " " " OMe Me N2.395 " " " " OMe Cl CH2.396 " " " " Me Me CH2.397 " " " Me OMe OMe CH2.398 " " " " OMe Me N2.399 " " CO.sub.2 -i-Pr H OMe OMe CH2.400 " " " " OMe Me N2.401 " " " " Me Me CH2.402 " " " Me OMe Me N2.403 n-Pr SO.sub.2 NMe.sub.2 CO.sub.2Me H OMe OMe CH2.404 " " " " " Cl CH2.405 " " " " Me Me CH2.406 " " " " OMe Me N2.407 " " " Me OMe OMe CH2.408 " " " " OMe Me N2.409 n-Pr " CO.sub.2Et H OMe Me N2.410 " " " " " OMe CH2.411 " " " " Me Me CH2.412 " " CO.sub.2 -n-Pr " OMe OMe CH2.413 i-Pr " CO.sub.2Me H OMe OMe CH2.414 " " " " OMe Me N2.415 " " " " Me Me CH2.416 " " " " Cl OMe N2.417 " " " Me OMe Me N2.418 " " " " " OMe CH2.419 Allyl " CO.sub.2Me H OMe OMe CH2.420 " " " " " Cl CH2.421 " " " " Me Me CH2.422 " " " " OMe Me N2.423 " " CO.sub.2Et H OMe OMe CH2.424 " " CO.sub.2 -n-Pr H OMe OMe CH2.425 " " CO.sub.2 -i-Pr " " " CH2.426 Me CHO ##STR22## H OMe OMe CH2.427 " " " H OMe Me N2.428 " " " " Me Me CH2.429 " COCH.sub.3 " " OMe OMe CH2.430 " " " " OMe Me N2.431 " " " " Me Me CH2.432 " COCH.sub.2 CH.sub.3 " " OMe OMe CH2.433 Et CHO " " " " CH2.434 Pr " " " " " CH2.435 Et COCH.sub.3 " " " " CH2.436 Pr " " " " " CH2.437 Et COCH.sub.2 CH.sub.3 " " " " CH2.438 Me ##STR23## " " " " CH2.439 Me CO.sub.2 Me " " " " CH2.440 Et " " " " " CH2.441 Pr " " " " " CH2.442 Me CONHEt " " " " CH2.443 Et " " " " " CH2.444 Pr " " " " " CH2.445 Me CHO ##STR24## H OMe OMe CH2.446 " " " H OMe Me N2.447 " " " " Me Me CH2.448 " COCH.sub.3 " " OMe OMe CH2.449 " " " " OMe Me N2.450 " " " " Me Me CH2.451 " COCH.sub.2 CH.sub.3 " " OMe OMe CH2.452 Et CHO " " " " CH2.453 Pr " " " " " CH2.454 Et COCH.sub.3 " " " " CH2.455 Pr " " " " " CH2.456 Et COCH.sub.2 CH.sub. 3 " " " " CH2.457 Me ##STR25## " " " " CH2.458 Me CO.sub.2 Me " " " " CH2.459 Et " " " " " CH2.460 Pr " " " " " CH2.461 Me CONHEt " " " " CH2.462 Et " " " " " CH2.463 Pr " " " " " CH2.464 Me CHO CO.sub.2NCHMe.sub.2 H OMe OMe CH2.465 " " " H OMe Me N2.466 " " " " Me Me CH2.467 " COCH.sub.3 " " OMe OMe CH2.468 " " " " OMe Me N2.469 " " " " Me Me CH2.470 " COCH.sub. 2 CH.sub.3 " " OMe OMe CH2.471 Et CHO " " " " CH2.472 Pr " " " " " CH2.473 Et COCH.sub.3 " " " " CH2.474 Pr " " " " " CH2.475 Et COCH.sub.2 CH.sub.3 " " " " CH2.476 Me ##STR26## " " " " CH2.477 Me CO.sub.2 Me " " " " CH2.478 Et " " " " " CH2.479 Pr " " " " " CH2.480 Me CONHEt " " " " CH2.481 Et " " " " " CH2.482 Pr " " " " " CH2.483 Me CHO CO.sub.2 CH.sub.2 CH.sub.2 Cl H OMe OMe CH2.484 " " " " OMe Me N2.485 " " " " Me Me CH2.486 " COCH.sub.3 " " OMe OMe CH2.487 " " " " OMe Me N2.488 " " " " Me Me CH2.489 " COCH.sub.2 CH.sub.3 " " OMe OMe CH2.490 Et CHO " " " " "2.491 Pr " " " " " "2.492 Et COCH.sub.3 " " " " "2.493 Pr " " " " " "2.494 Et COCH.sub.2 CH.sub.3 " " " " "2.495 Me ##STR27## " " " " "2.496 Me CO.sub.2 Me " " " " "2.497 Et " " " " " "2.498 Pr " " " " " "2.499 Me CONHEt " " " " "2.500 Et " " " " " "2.501 Pr " " " " " "2.502 Me CHO CO.sub.2 (CH.sub.2).sub.2 OMe H OMe OMe CH2.503 " " " H OMe Me N2.504 " " " " Me Me CH2.505 " COCH.sub.3 " " OMe OMe CH2.506 " " " " OMe Me N2.507 " " " " Me Me CH2.508 " COCH.sub.2 CH.sub.3 " " OMe OMe CH2.509 Et CHO " " " " "2.510 Pr " " " " " "2.511 Et COCH.sub.3 " " " " "2.512 Pr " " " " " "2.513 Et COCH.sub.2 CH.sub.3 " " " " "2.514 Me ##STR28## " " " " "2.515 Me CO.sub.2 Me " " " " "2.516 Et " " " " " "2.517 Pr " " " " " "2.518 Me CONHEt " " " " "2.519 Et " " " " " "2.520 Pr " " " " " "2.521 Me CHO CO.sub.2 CH.sub.2 CCl.sub.3 H OMe OMe CH2.522 " " " H OMe Me N2.523 " " " " Me Me CH2.524 " COCH.sub.3 " " OMe OMe CH2.525 " " " " OMe Me N2.526 " " " " Me Me CH2.527 " COCH.sub.2 CH.sub.3 " " OMe OMe CH2.528 Et CHO " " " " "2.529 Pr " " " " " "2.530 Et COCH.sub.3 " " " " "2.531 Pr " " " " " "2.532 Et COCH.sub.2 CH.sub.3 " " " " "2.533 Me ##STR29## " " " " "2.534 Me CO.sub.2 Me " " " " "2.535 Et " " " " " "2.536 Pr " " " " " "2.537 Me CONHEt " " " " "2.538 Et " " " " " "2.539 Pr " " " " " "__________________________________________________________________________
__________________________________________________________________________No. R.sup.1 R.sup.2 R.sup.3 R.sup.4 X Y Z m.p.__________________________________________________________________________2.540 Me CHO CO.sub.2 CH.sub.2 CCH H OMe OMe CH2.541 " " " H OMe Me N2.542 " " " " Me Me CH2.543 " COCH.sub.3 " " OMe OMe CH2.544 " " " " OMe Me N2.545 " " " " Me Me CH2.546 " COCH.sub.2 CH.sub.3 " " OMe OMe CH2.547 Et CHO " " " " "2.548 Pr " " " " " "2.549 Et COCH.sub.3 " " " " "2.550 Pr " " " " " "2.551 Et COCH.sub.2 CH.sub.3 " " " " "2.552 Me ##STR30## " " " " "2.553 Me CO.sub.2 Me " " " " "2.554 Et " " " " " "2.555 Pr " " " " " "2.556 Me CONHEt " " " " "2.557 Et " " " " " "2.558 Pr " " " " " "2.559 Me SO.sub.2 Et CO.sub.2 Me H OMe OMe CH2.560 " " " " " OMe N2.561 " " " " " Me N2.562 " " " " " " CH2.563 " " " " NMe.sub.2 OCH.sub.2 CF.sub. N2.564 " " " " Me Me CH2.565 " " " " " " N2.566 " " " " Cl OMe CH2.567 " " " Me OMe OMe CH2.568 " " " " " Me N2.569 " " CO.sub.2 Et H OMe OMe CH2.570 " " " " " Cl CH2.571 " " " " Me Me CH2.572 " " " " OMe Me N2.573 " " " " NMe.sub.2 OCH.sub.2 CF.sub.3 N2.574 " " " Me OMe OMe CH2.575 " " " " OMe Me N2.576 " " CO.sub.2 -n-Pr H OMe OMe CH2.577 " " " " " " N2.578 " " " " OMe Me N2.579 " " " " Me Me CH2.580 " " " " OMe Cl CH2.581 " " " Me Me OMe N2.582 " " " " OMe OMe CH2.583 Me SO.sub.2 Et CO.sub.2 -i-Pr H OMe OMe CH2.584 " " " " " " N2.585 " " " " OMe Me N2.586 " " " " OMe Cl CH2.587 " " " " Me Me CH2.588 " " " " SMe NEt.sub.2 N2.589 " " CO.sub.2 -i-Pr Me OMe Me N2.590 " " " " OMe OMe CH2.591 Me " CO.sub.2 -allyl H OMe OMe CH2.592 Et " CO.sub.2 Me H OMe OMe CH2.593 " " " H OMe Me N2.594 " " " " Me Me CH2.595 " " " " Cl OMe CH2.596 " " " Me OMe OMe CH2.597 " " " " OMe Me N2.598 " " CO.sub.2 Et H OMe OMe CH2.599 " " " " OMe Me CH2.600 " " " " Cl OMe CH2.601 " " " " OMe Me N2.602 " " " Me OMe OMe CH2.603 " " " " " Me N2.604 " " CO.sub.2 -n-Pr H OMe OMe CH2.605 " " " " OMe Me N2.606 " " " " OMe Cl CH2.607 " " " " Me Me CH2.608 " " " Me OMe OMe CH2.609 " " " " OMe Me N2.610 " " CO.sub.2 -i-Pr H OMe OMe CH2.611 " " " " OMe Me N2.612 " " " " Me Me CH2.613 " " " Me OMe Me N2.614 n-Pr SO.sub.2 Et CO.sub.2 Me H OMe OMe CH2.615 " " " " " Cl CH2.616 " " " " Me Me CH2.617 " " " " OMe Me N2.618 " " " Me OMe OMe CH2.619 " " " " OMe Me N2.620 n-Pr " CO.sub.2 Et H " " N2.621 " " " " " OMe CH2.622 " " " " Me Me CH2.623 " " CO.sub.2 -n-Pr " OMe OMe CH2.624 i-Pr " CO.sub.2 Me H " " CH2.625 " " " " " Me N2.626 " " " " Me Me CH2.627 " " " " Cl OMe N2.628 " " " Me OMe Me N2.629 " " " " " OMe CH2.630 Allyl " CO.sub.2 Me H OMe OMe CH2.631 " " " " " Cl CH2.632 " " " " Me Me CH2.633 " " " " OMe Me N2.634 " " CO.sub.2Et H OMe OMe CH2.635 " " CO.sub.2 -n-Pr H OMe OMe CH2.636 " " CO.sub.2 -i-Pr " " " CH2.637 Me SO.sub.2 CH.sub.2 Cl CO.sub.2Me H OMe OMe CH2.638 " " " " " OMe N2.639 " " " " " Me N2.640 " " " " " " CH2.641 " " " " NMe.sub.2 OCH.sub.2 CF.sub.3 N2.642 " " " " Me Me CH2.643 " " " " " " N2.644 " " " " Cl OMe CH2.645 " " " Me OMe OMe CH2.646 " " " " " Me N2.647 " " CO.sub.2Et H OMe OMe CH2.648 " " " " " Cl CH2.649 " " " " Me Me CH2.650 " " " " OMe Me N2.651 " " " " NMe.sub.2 OCH.sub.2 CF.sub.3 N2.652 " " " Me OMe OMe CH2.653 " " " " OMe Me N2.654 " " CO.sub.2 -n-Pr H OMe OMe CH2.655 " " " " " " N2.656 " " " " OMe Me N2.657 " " " " Me Me CH2.658 " " " " OMe Cl CH2.659 " " " Me Me OMe N2.660 " " " " OMe OMe CH2.661 Me SO.sub.2 CH.sub.2 Cl CO.sub.2 -i-Pr H OMe OMe CH2.662 " " " " " " N2.663 " " " " OMe Me N2.664 " " " " OMe Cl CH2.665 " " " " Me Me CH2.666 " " " " SMe NEt.sub.2 N2.667 " " CO.sub.2 -i-Pr Me OMe Me N2.668 " " " " OMe OMe CH2.669 Me " CO.sub.2 -Allyl H OMe OMe CH2.670 Et " CO.sub.2Me H OMe OMe CH2.671 " " " H OMe Me N2.672 " " " " Me Me CH2.673 " " " " Cl OMe CH2.674 " " " Me OMe OMe CH2.675 " " " " OMe Me N2.676 " " CO.sub.2Et H OMe OMe CH2.677 " " " " OMe Me CH2.678 " " " " Cl OMe CH2.679 " " " " OMe Me N2.680 " " " Me OMe OMe CH2.681 " " " " " Me N2.682 " " CO.sub.2 -n-Pr H OMe OMe CH2.683 " " " " OMe Me N2.684 " " " " OMe Cl CH2.685 " " " " Me Me CH2.686 " " " Me OMe OMe CH2.687 " " " " " Me N2.688 " " CO.sub.2 i-Pr H OMe OMe CH2.689 " " " " OMe Me N2.690 " " " " Me Me CH2.691 " " " Me OMe Me N2.692 n-Pr SO.sub.2 CH.sub.2 Cl CO.sub.2Me H OMe OMe CH2.693 " " " " " Cl CH2.694 " " " " Me Me CH2.695 " " " " OMe Me N2.696 " " " Me OMe OMe CH2.697 " " " " " Me N2.698 n-Pr " CO.sub.2Et H " " N2.699 " " " " " OMe CH2.700 " " " " Me Me CH2.701 " " CO.sub.2 -n-Pr " OMe OMe CH2.702 i-Pr " CO.sub.2Me H OMe OMe CH2.703 " " " " OMe Me N2.704 " " " " Me Me CH2.705 " " " " Cl OMe N2.706 " " " Me OMe Me N2.707 " " " " " OMe CH2.708 Allyl " CO.sub.2Me H OMe OMe CH2.709 " " " " " Cl CH2.710 " " " " Me Me CH2.711 " " " " OMe Me N2.712 " " CO.sub.2Et H OMe OMe CH2.713 " " CO.sub.2 -n-Pr " " " CH2.714 " " CO.sub.2 -i-Pr " " " CH2.715 Me SO.sub.2 CH.sub.3 CO.sub.2Me H OMe OMe CH 119.degree. C.2.716 " " " " " OMe N2.717 " " " " " Me N2.718 " " " " " " CH2.719 " " " " NMe.sub.2 OCH.sub.2 CF.sub.3 N2.720 " " " " Me Me CH2.721 " " " " " " N2.722 " " " " Cl OMe CH2.723 " " " Me OMe OMe CH2.724 " " " " " Me N2.725 " " CO.sub.2Et H OMe OMe CH2.726 " " " " " Cl CH2.727 " " " " Me Me CH2.728 " " " " OMe Me N2.729 " " " " NMe.sub.2 OCH.sub.2 CF.sub.3 N2.730 " " " Me OMe OMe CH2.731 " " " " OMe Me N2.732 " " CO.sub.2 -n-Pr H OMe OMe CH2.733 " " " " " " N2.734 " " " " OMe Me N2.735 " " " " Me Me CH2.736 " " " " OMe Cl CH2.737 " " " Me Me OMe N2.738 " " " " OMe OMe CH2.739 Me SO.sub.2 Me CO.sub.2 -i-Pr H OMe OMe CH2.740 " " " " " " N2.741 " " " " OMe Me N2.742 " " " " OMe Cl CH2.743 " " " " Me Me CH2.744 " " " " SMe NEt.sub.2 N2.745 " " CO.sub.2 -i-Pr Me OMe Me N2.746 " " " " OMe OMe CH2.747 Me " CO.sub.2 -Allyl H OMe OMe CH2.748 Et " CO.sub.2Me H OMe OMe CH2.749 " " " H OMe Me N2.750 " " " " Me Me CH2.751 " " " " Cl OMe CH2.752 " " " Me OMe OMe CH2.753 " " " " OMe Me N2.754 " " CO.sub.2Et H OMe OMe CH2.755 " " " " OMe Me CH2.756 " " " " Cl OMe CH2.757 " " " " OMe Me N2.758 " " " Me OMe OMe CH2.759 " " " " " Me N2.760 " " CO.sub.2 -n-Pr H OMe OMe CH2.761 " " " " OMe Me N2.762 " " " " OMe Cl CH2.763 " " " " Me Me CH2.764 " " " Me OMe OMe CH2.765 " " " " OMe Me N2.766 " " CO.sub.2 -i-Pr H OMe OMe CH2.767 " " " " OMe Me N2.768 " " " " Me Me CH2.769 " " " Me OMe Me N2.770 n-Pr SO.sub.2 Me CO.sub.2Me H OMe OMe CH2.771 " " " " " Cl CH2.772 " " " " Me Me CH2.773 " " " " OMe Me N2.774 " " " Me OMe OMe CH2.775 " " " " OMe Me N2.776 n-Pr " CO.sub.2Et H " " N2.777 " " " " " OMe CH2.778 " " " " Me Me CH2.779 " " CO.sub.2 -n-Pr " OMe OMe CH2.780 i-Pr " CO.sub.2Me H OMe OMe CH2.781 " " " " OMe Me N2.782 " " " " Me Me CH2.783 " " " " Cl OMe N2.784 " " " Me OMe Me N2.785 " " " " " OMe CH2.786 Allyl " CO.sub.2Me H OMe OMe CH2.787 " " " " " Cl CH2.788 Allyl " CO.sub.2Me H OMe OMe CH2.789 " " " " " Cl CH2.790 " " " " Me Me CH2.791 " " " " OMe Me N2.792 " " CO.sub.2Et H OMe OMe CH2.793 " " CO.sub.2 -n-Pr " " " CH2.794 " " CO.sub.2 -i-Pr " " " CH2.795 Me CONH CO.sub.2Me H OMe OMe CH CH.sub.2 CH.sub.2 Cl2.796 " CONH " " " OMe N CH.sub.2 CH.sub.2 Cl2.797 " CONH " " " Me N CH.sub.2 CH.sub.2 Cl2.798 " CONH " " " " CH CH.sub.2 CH.sub.2 Cl2.799 " CONH " " NMe.sub.2 OCH.sub.2 CF.sub.3 N CH.sub.2 CH.sub.2 Cl2.800 " CONH " " Me Me CH CH.sub.2 CH.sub. 2 Cl2.801 " CONH " " " " N CH.sub.2 CH.sub.2 Cl2.802 " CONH " " Cl OMe CH CH.sub.2 CH.sub.2 Cl2.803 " CONH " Me OMe OMe CH CH.sub.2 CH.sub.2 Cl2.804 " CONH " " " Me N CH.sub.2 CH.sub.2 Cl2.805 " CONH CO.sub.2Et H OMe OMe CH CH.sub.2 CH.sub.2 Cl2.806 " CONH " " " Cl CH CH.sub.2 CH.sub.2 Cl2.807 " CONH " " Me Me CH CH.sub.2 CH.sub.2 Cl2.808 " CONH " " OMe Me N CH.sub.2 CH.sub.2 Cl2.809 " CONH " " NMe.sub.2 OCH.sub.2 CF.sub.3 N CH.sub.2 CH.sub.2 Cl2.810 " CONH " Me OMe OMe CH CH.sub.2 CH.sub.2 Cl2.811 " CONH " " OMe Me N CH.sub.2 CH.sub.2 Cl2.812 " CONH CO.sub.2 -n-Pr H OMe OMe CH CH.sub.2 CH.sub.2 Cl2.813 " CONH " " " " N CH.sub.2 CH.sub.2 Cl2.814 " CONH " " OMe Me N CH.sub.2 CH.sub.2 Cl2.815 " CONH " " Me Me CH CH.sub.2 CH.sub.2 Cl2.816 " CONH " " OMe Cl CH CH.sub.2 CH.sub.2 Cl2.817 " CONH " Me Me OMe N CH.sub.2 CH.sub.2 Cl2.818 " CONH " " OMe OMe CH CH.sub.2 CH.sub.2 Cl2.819 Me CO CO.sub.2 -i-Pr H OMe OMe CH NHCH.sub.2 CH.sub.2 Cl2.820 " CO " " " " N NHCH.sub.2 CH.sub.2 Cl2.821 " CO " " OMe Me N NHCH.sub.2 CH.sub.2 Cl2.822 " CO " " OMe Cl CH NHCH.sub.2 CH.sub.2 Cl2.823 " CO " " Me Me CH NHCH.sub.2 CH.sub.2 Cl2.824 " CO " " SMe NEt.sub.2 N NHCH.sub.2 CH.sub.2 Cl2.825 " CO CO.sub.2 -i-Pr Me OMe Me N NHCH.sub.2 CH.sub.2 Cl2.826 " CO " " OMe OMe CH NHCH.sub.2 CH.sub.2 Cl2.827 Me CO CO.sub.2 -Allyl H OMe OMe CH NHCH.sub.2 CH.sub.2 Cl2.828 Et CO CO.sub.2Me H OMe OMe CH NHCH.sub.2 CH.sub.2 Cl2.829 " CO " H OMe Me N NHCH.sub.2 CH.sub.2 Cl2.830 " CO " " Me Me CH NHCH.sub.2 CH.sub.2 Cl2.831 " CO " " Cl OMe CH NHCH.sub.2 CH.sub.2 Cl2.832 " CO " Me OMe OMe CH NHCH.sub.2 CH.sub.2 Cl2.833 " CO " " OMe Me N NHCH.sub.2 CH.sub.2 Cl2.834 " CO CO.sub.2Et H OMe OMe CH NHCH.sub.2 CH.sub.2 Cl2.835 " CO " " OMe Me CH NHCH.sub.2 CH.sub.2 Cl2.836 " CO " " Cl OMe CH NHCH.sub.2 CH.sub.2 Cl2.837 " CO " " OMe Me N NHCH.sub.2 CH.sub.2 Cl2.838 " CO " Me OMe OMe CH NHCH.sub. 2 CH.sub.2 Cl2.839 " CO " " " Me N NHCH.sub.2 CH.sub.2 Cl2.840 " CO CO.sub.2 -n-Pr H OMe OMe CH NHCH.sub.2 CH.sub.2 Cl2.841 " CO " H OMe Me N NHCH.sub.2 CH.sub.2 Cl2.842 " CO " " OMe Cl CH NHCH.sub.2 CH.sub.2 Cl2.843 " CO " " Me Me CH NHCH.sub.2 CH.sub.2 Cl2.844 " CO " Me OMe OMe CH NHCH.sub.2 CH.sub.2 Cl2.845 " CO " " OMe Me N NHCH.sub.2 CH.sub.2 Cl2.846 " CO CO.sub.2 -i-Pr H OMe OMe CH NHCH.sub.2 CH.sub.2 Cl2.847 " CO " H OMe Me N NHCH.sub.2 CH.sub.2 Cl2.848 " CO " " Me Me CH NHCH.sub.2 CH.sub.2 Cl2.849 " CO " Me OMe Me N NHCH.sub.2 CH.sub.2 Cl2.850 n-Pr CONH CO.sub.2Me H OMe OMe CH CH.sub.2 CH.sub.2 Cl2.851 " CONH " " " Cl CH CH.sub.2 CH.sub.2 Cl2.852 " CONH " " Me Me CH CH.sub.2 CH.sub.2 Cl2.853 " CONH " " OMe Me N CH.sub.2 CH.sub.2 Cl2.854 " CONH " Me OMe OMe CH CH.sub.2 CH.sub.2 Cl2.855 " CONH " " OMe Me N CH.sub.2 CH.sub.2 Cl2.856 n-Pr CONH CO.sub.2Et H " " N CH.sub.2 CH.sub.2 Cl2.857 " CONH " " " OMe CH CH.sub.2 CH.sub.2 Cl2.858 " CONH " " Me Me CH CH.sub.2 CH.sub.2 Cl2.859 " CONH CO.sub.2 -n-Pr " OMe OMe CH CH.sub.2 CH.sub.2 Cl2.860 i-Pr CONH CO.sub.2Me H OMe OMe CH CH.sub.2 CH.sub.2 Cl2.861 " CONH " " OMe Me N CH.sub.2 CH.sub.2 Cl2.862 " CONH " " Me Me CH CH.sub.2 CH.sub.2 Cl2.863 " CONH " " Cl OMe N CH.sub.2 CH.sub.2 Cl2.864 " CONH " Me OMe Me N CH.sub.2 CH.sub.2 Cl2.865 " CONH " " " OMe CH CH.sub.2 CH.sub.2 Cl2.866 Allyl CONH CO.sub.2Me H OMe OMe CH CH.sub.2 CH.sub.2 Cl2.867 " CONH " " " Cl CH CH.sub.2 CH.sub.2 Cl2.868 " CONH " " Me Me CH CH.sub.2 CH.sub.2 Cl2.869 " CONH " " OMe Me N CH.sub.2 CH.sub.2 Cl2.870 " CONH CO.sub.2Et H OMe OMe CH CH.sub.2 CH.sub.2 Cl2.871 " CONH CO.sub.2 -n-Pr " " " CH CH.sub.2 CH.sub.2 Cl2.872 " CONH CO.sub.2 -i-Pr " " " CH CH.sub.2 CH.sub.2 Cl2.873 Me COOCH.sub.2 CCl.sub.3 CO.sub.2Me H OMe OMe CH2.874 " " " " " OMe N2.875 " " " " " Me N2.876 " " " " " " CH2.877 " " " " NMe.sub.2 OCH.sub.2 CF.sub.3 N2.878 " " " " Me Me CH2.879 " " " " " " N2.880 " " " " Cl OMe CH2.881 " " " Me OMe OMe CH2.882 " " " " " Me N2.883 " " CO.sub.2Et H OMe OMe CH2.884 " " " " " Cl CH2.885 " " " " Me Me CH2.886 " " " " OMe Me N2.887 " " " " NMe.sub.2 OCH.sub.2 CF.sub.3 N2.888 " " " Me OMe OMe CH2.889 " " " " OMe Me N2.890 " " CO.sub.2 -n-Pr H OMe OMe CH2.891 " " " " " " N2.892 " " " " OMe Me N2.893 " " " " Me Me CH2.894 " " " " OMe Cl CH2.895 " " " Me Me OMe N2.896 " " " " OMe OMe CH2.897 Me COOCH.sub.2 CCl.sub.3 CO.sub.2 -i-Pr H OMe OMe CH2.898 " " " " " " N2.899 " " " " OMe Me N2.900 " " " " OMe Cl CH2.901 " " " " Me Me CH2.902 " " " " SMe NEt.sub.2 N2.903 " " CO.sub.2 -i-Pr Me OMe Me N2.904 " " " " OMe OMe CH2.905 Me " CO.sub.2 -Allyl H OMe OMe CH2.906 Et " CO.sub.2Me H OMe OMe CH2.907 " " " H OMe Me N2.908 " " " " Me Me CH2.909 " " " " Cl OMe CH2.910 " " " Me OMe OMe CH2.911 " " " " OMe Me N2.912 " " CO.sub.2Et H OMe OMe CH2.913 " " " " OMe Me CH2.914 " " " " Cl OMe CH2.915 " " " " OMe Me N2.916 " " " Me OMe OMe CH2.917 " " " " " Me N2.918 " " CO.sub.2 -n-Pr H OMe OMe CH2.919 " " " " OMe Me N2.920 " " " " OMe Cl CH2.921 " " " " Me Me CH2.922 " " " Me OMe OMe CH2.923 " " " " OMe Me N2.924 " " CO.sub.2 -i-Pr H OMe OMe CH2.925 " " " " OMe Me N2.926 " " " " Me Me CH2.927 " " " Me OMe Me N2.928 n-Pr COOCH.sub.2 CCl.sub.3 CO.sub.2Me H OMe OMe CH2.929 " " " " " Cl CH2.930 " " " " Me Me CH2.931 " " " " OMe Me N2.932 " " " Me OMe OMe CH2.933 " " " " OMe Me N2.934 n-Pr " CO.sub.2Et H OMe Me N2.935 " " " " " OMe CH2.936 " " " " Me Me CH2.937 " " CO.sub.2 -n-Pr " OMe OMe CH2.938 i-Pr " CO.sub.2Me H OMe OMe CH2.939 " " " " OMe Me N2.940 " " " " Me Me CH2.941 " " " " Cl OMe N2.942 " " " Me OMe Me N2.943 " " " " " OMe CH2.944 Allyl " CO.sub.2Me H OMe OMe CH2.945 " " " " " Cl CH2.946 " " " " Me Me CH2.947 " " " " OMe Me N2.948 " " CO.sub.2Et H OMe OMe CH2.949 " " CO.sub.2 -n-Pr H OMe OMe CH2.950 " " CO.sub.2 -i-Pr " " " CH2.951 Me COCH.sub.2 Br CO.sub.2Me H OMe OMe CH2.952 " " " " " OMe N2.953 " " " " " Me N2.954 " " " " " " CH2.955 " " " " NMe.sub.2 OCH.sub.2 CF.sub.3 N2.956 " " " " Me Me CH2.957 " " " " " " N2.958 " " " " Cl OMe CH2.959 " " " Me OMe OMe CH2.960 " " " " " Me N2.961 " " CO.sub.2Et H OMe OMe CH2.962 " " " " " Cl CH2.963 " " " " Me Me CH2.964 " " " " OMe Me N2.965 " " " " NMe.sub.2 OCH.sub.2 CF.sub.3 N2.966 " " " Me OMe OMe CH2.967 " " " " OMe Me N2.968 " " CO.sub.2 -n-Pr H OMe OMe CH2.969 " " " " " " N2.970 " " " " OMe Me N2.971 " " " " Me Me CH2.972 " " " " OMe Cl CH2.973 " " " Me Me OMe N2.974 " " " " OMe OMe CH2.975 Me COCH.sub.2 Br CO.sub.2 -i-Pr H OMe OMe CH2.976 " " " " " " N2.977 " " " " H Me N2.978 " " " " OMe Cl CH2.979 " " " " Me Me CH2.980 " " " " SMe NEt.sub.2 N2.981 " " CO.sub.2 -i-Pr Me OMe Me N2.982 " " " " OMe OMe CH2.983 Me " CO.sub.2 -Allyl H OMe OMe CH2.984 Et " CO.sub.2Me H OMe OMe CH2.985 " " " H OMe Me N2.986 " " " " Me Me CH2.987 " " " " Cl OMe CH2.988 " " " Me OMe OMe CH2.989 " " " " OMe Me N2.990 " " CO.sub.2Et H OMe OMe CH2.991 " " " " OMe Me CH2.992 " " " " Cl OMe CH2.993 " " " " OMe Me N2.994 " " " Me OMe OMe CH2.995 " " " " " Me N2.996 " " CO.sub.2 -n-Pr H OMe OMe CH2.997 " " " " OMe Me N2.998 " " " " OMe Cl CH2.999 " " " " Me Me CH3.000 " " " Me OMe OMe CH3.001 " " " " OMe Me N3.002 " " CO.sub.2 -i-Pr H OMe OMe CH3.003 " " " " OMe Me N3.004 " " " " Me Me CH3.005 " " " Me OMe Me N3.006 n-Pr COCH.sub.2 Br CO.sub.2Me H OMe OMe CH3.007 " " " " " Cl CH3.008 " " " " Me Me CH3.009 " " " " OMe Me N3.010 " " " Me OMe OMe CH3.011 " " " " OMe Me N3.012 n-Pr " CO.sub.2Et H " " N3.013 " " " " " OMe CH3.014 " " " " Me Me CH3.015 " " CO.sub.2 -n-Pr " OMe OMe CH3.016 i-Pr " CO.sub.2Me H OMe OMe CH3.017 " " " " OMe Me N3.018 " " " " Me Me CH3.019 " " " " Cl OMe N3.020 " " " Me OMe Me N3.021 " " " " " OMe CH3.022 Allyl " CO.sub.2Me H OMe OMe CH3.023 " " " " " Cl CH3.024 " " " " Me Me CH3.025 " " " " OMe Me N3.026 " " CO.sub.2Et H OMe OMe CH3.027 " " CO.sub.2 -n-Pr " " " CH3.028 " " CO.sub.2 -i-Pr " " " CH3.029 Me COCCl.sub.3 CO.sub.2Me H OMe OMe CH3.030 " " " " " OMe N3.031 " " " " " Me N3.032 " " " " " " CH3.033 " " " " NMe.sub.2 OCH.sub.2 CF.sub.3 N3.034 " " " " Me Me CH3.035 " " " " " " N3.036 " " " " Cl OMe CH3.037 " " " Me OMe OMe CH3.038 " " " " " Me N3.039 " " CO.sub.2Et H OMe OMe CH3.040 " " " " " Cl CH3.041 " " " " Me Me CH3.042 " " " " OMe Me N3.043 " " " " NMe.sub.2 OCH.sub.2 CF.sub.3 N3.044 " " " Me OMe OMe CH3.045 " " " " OMe Me N3.046 " " CO.sub.2 -n-Pr H OMe OMe CH3.047 " " " " " " N3.048 " " " " OMe Me N3.049 " " " " Me Me CH3.050 " " " " OMe Cl CH3.051 " " " Me Me OMe N3.052 " " " " OMe OMe CH3.053 Me COCCl.sub.3 CO.sub.2 -i-Pr H OMe OMe CH3.054 " " " " " " N3.055 " " " " OMe Me N3.056 " " " " OMe Cl CH3.057 " " " " Me Me CH3.058 " " " " SMe NEt.sub.2 N3.059 " " CO.sub.2 -i-Pr Me OMe Me N3.060 " " " " OMe OMe CH3.061 Me " CO.sub.2 -Allyl H OMe OMe CH3.062 Et " CO.sub.2Me H OMe OMe CH3.063 " " " H OMe Me N3.064 " " " " Me Me CH3.065 " " " " Cl OMe CH3.066 " " " Me OMe OMe CH3.067 " " " " OMe Me N3.068 " " CO.sub.2Et H OMe OMe CH3.069 " " " " OMe Me CH3.070 " " " " Cl OMe CH3.071 " " " " OMe Me N3.072 " " " Me OMe OMe CH3.073 " " " " " Me N3.074 " " CO.sub.2 -n-Pr H OMe OMe CH3.075 " " " " OMe Me N3.076 " " " " OMe Cl CH3.077 " " " " Me Me CH3.078 " " " Me OMe OMe CH3.079 " " " " OMe Me N3.080 " " CO.sub.2 -i-Pr H OMe OMe CH3.081 " " " " OMe Me N3.082 " " " " Me Me CH3.083 " " " Me OMe Me N3.084 n-Pr COCCl.sub.3 CO.sub.2Me H OMe OMe CH3.085 " " " " " Cl CH3.086 " " " " Me Me CH3.087 " " " " OMe Me N3.088 " " " Me OMe OMe CH3.089 " " " " OMe Me N3.090 n-Pr " CO.sub.2Et H " " N3.091 " " " " " OMe CH3.092 " " " " Me Me CH3.093 " " CO.sub.2 -n-Pr " OMe OMe CH3.094 i-Pr " CO.sub.2Me H OMe OMe CH3.095 " " " " OMe Me N3.096 " " " " Me Me CH3.097 " " " " Cl OMe N3.098 " " " Me OMe Me N3.099 " " " " " OMe CH3.100 Allyl " CO.sub.2Me H OMe OMe CH3.101 " " " " " Cl CH3.102 " " " " Me Me CH3.103 " " " " OMe Me N3.104 " " CO.sub.2Et H OMe OMe CH3.105 " " CO.sub.2 -n-Pr " " " CH3.106 " " CO.sub.2 -i-Pr " " " CH3.107 Me COCHCl.sub.2 CO.sub.2Me H OMe OMe CH3.108 " " " " " OMe N3.109 " " " " " Me N3.110 " " " " " " CH3.111 " " " " NMe.sub.2 OCH.sub.2 CF.sub.3 N3.112 " " " " Me Me CH3.113 " " " " " " N3.114 " " " " Cl OMe CH3.115 " " " Me OMe OMe CH3.116 " " " " " Me N3.117 " " CO.sub.2Et H OMe OMe CH3.118 " " " " " Cl CH3.119 " " " " Me Me CH3.120 " " " " OMe Me N3.121 " " " " NMe.sub.2 OCH.sub.2 CF.sub.3 N3.122 " " " Me OMe OMe CH3.123 " " " " OMe Me N3.124 " " CO.sub.2 -n-Pr H OMe OMe CH3.125 " " " " " " N3.126 " " " " OMe Me N3.127 " " " " Me Me CH3.128 " " " " OMe Cl CH3.129 " " " Me Me OMe N3.130 " " " " OMe OMe CH3.131 Me COCHCl.sub.2 CO.sub.2 -i-Pr H OMe OMe CH3.132 " " " " " " N3.133 " " " " OMe Me N3.134 " " " " OMe Cl CH3.135 " " " " Me Me CH3.136 " " " " SMe NEt.sub.2 N3.137 " " CO.sub.2 -i-Pr Me OMe Me N3.138 " " " " OMe OMe CH3.139 Me " CO.sub.2 -Allyl H OMe OMe CH3.140 Et " CO.sub.2Me H OMe OMe CH3.141 " " " H OMe Me N3.142 " " " " Me Me CH3.143 " " " " Cl OMe CH3.144 " " " Me OMe OMe CH3.145 " " " " OMe Me N3.146 " " CO.sub.2Et H OMe OMe CH3.147 " " " " OMe Me CH3.148 " " " " Cl OMe CH3.149 " " " " OMe Me N3.150 " " " Me OMe OMe CH3.151 " " " " " Me N3.152 " " CO.sub.2 -n-Pr H OMe OMe CH3.153 " " " " OMe Me N3.154 " " " " OMe Cl CH3.155 " " " " Me Me CH3.156 " " " Me OMe OMe CH3.157 " " " " OMe Me N3.158 " " CO.sub.2 -i-Pr H OMe OMe CH3.159 " " " " OMe Me N3.160 " " " " Me Me CH3.161 " " " Me OMe Me N3.162 n-Pr COCHCl.sub.2 CO.sub.2Me H OMe OMe CH3.163 " " " " " Cl CH3.164 " " " " Me Me CH3.165 " " " " OMe Me N3.166 " " " Me OMe OMe CH3.167 " " " " OMe Me N3.168 n-Pr " CO.sub.2Et H " " N3.169 " " " " " OMe CH3.170 " " " " Me Me CH3.171 " " CO.sub.2 -n-Pr " OMe OMe CH3.172 i-Pr " CO.sub.2Me H OMe OMe CH3.173 " " " " OMe Me N3.174 " " " " Me Me CH3.175 " " " " Cl OMe N3.176 " " " Me OMe Me N3.177 " " " " " OMe CH3.178 Allyl " CO.sub.2Me H OMe OMe CH3.179 " " " " " Cl CH3.180 " " " " Me Me CH3.181 " " " " OMe Me N3.182 " " CO.sub.2Et H OMe OMe CH3.183 " " CO.sub.2 -n-Pr " " " CH3.184 " " CO.sub.2 -i-Pr " " " CH3.185 Me COCH.sub.2 Cl CO.sub.2Me H OMe OMe CH3.186 " " " " " OMe N3.187 " " " " " Me N3.188 " " " " " " CH3.189 " " " " NMe.sub.2 OCH.sub.2 CF.sub.3 N3.190 " " " " Me Me CH3.191 " " " " " " N3.192 " " " " Cl OMe CH3.193 " " " Me OMe OMe CH3.194 " " " " " Me N3.195 " " CO.sub.2Et H OMe OMe CH3.196 " " " " " Cl CH3.197 " " " " Me Me CH3.198 " " " " OMe Me N3.199 " " " " NMe.sub.2 OCH.sub.2 CF.sub.3 N3.200 " " " Me OMe OMe Ch3.201 " " " " OMe Me N3.202 " " CO.sub.2 -n-Pr H OMe OMe CH3.203 " " " " " " N3.204 " " " " OMe Me N3.205 " " " " Me Me CH3.206 " " " " OMe Cl CH3.207 " " " Me Me OMe N3.208 " " " " OMe OMe CH3.209 Me COCH.sub.2 Cl CO.sub.2 -i-Pr H OMe OMe CH3.210 " " " " " " N3.211 " " " " OMe Me N3.212 " " " " OMe Cl CH3.213 " " " " Me Me CH3.214 " " " " SMe NEt.sub.2 N3.215 " " CO.sub.2 -i-Pr Me OMe Me N3.216 " " " " OMe OMe CH3.217 Me " CO.sub.2 -Allyl H OMe OMe CH3.218 Et " CO.sub.2Me H OMe OMe CH3.219 " " " H OMe Me N3.220 " " " " Me Me CH3.221 " " " " Cl OMe CH3.222 " " " Me OMe OMe CH3.223 " " " " OMe Me N3.224 " " CO.sub.2Et H OMe OMe CH3.225 " " " " OMe Me CH3.226 " " " " Cl OMe CH3.227 " " " " OMe Me N3.228 " " " Me OMe OMe CH3.229 " " " " " Me N3.230 " " CO.sub.2 -n-Pr H OMe OMe CH3.231 " " " " OMe Me N3.232 " " " " OMe Cl CH3.233 " " " " Me Me CH3.234 " " " Me OMe OMe CH3.235 " " " " OMe Me N3.236 " " CO.sub.2 -i-Pr H OMe OMe CH3.237 " " " " OMe Me N3.238 " " " " Me Me CH3.239 " " " Me OMe Me N3.240 n-Pr COCH.sub.2 Cl CO.sub.2Me H OMe OMe CH3.241 " " " " " Cl CH3.242 " " " " Me Me CH3.243 " " " " OMe Me N3.244 " " " Me OMe OMe CH3.245 " " " " OMe Me N3.246 n-Pr " CO.sub.2Et H " " N3.247 " " " " " OMe CH3.248 " " " " Me Me CH3.249 " " CO.sub.2 -n-Pr " OMe OMe CH3.250 i-Pr " CO.sub.2Me H OMe OMe CH3.251 " " " " OMe Me N3.252 " " " " Me Me CH3.253 " " " " Cl OMe N3.254 " " " Me OMe Me N3.255 " " " " " OMe CH3.256 Allyl " CO.sub.2Me H OMe OMe CH3.257 " " " " " Cl CH3.258 " " " " Me Me CH3.259 " " " " OMe Me N3.260 " " CO.sub.2Et H OMe OMe CH3.261 " " CO.sub.2 -n-Pr " " " CH3.262 " " CO.sub.2 -i-Pr " " " CH3.263 Me COCF.sub.3 CO.sub.2 Me H OMe OMe CH3.264 " " " " " OMe N3.265 " " " " " Me N3.266 " " " " " " CH3.267 " " " " NMe.sub.2 OCH.sub.2 CF.sub.3 N3.268 " " " " Me Me CH3.269 " " " " " " N3.270 " " " " Cl OMe CH3.271 " " " Me OMe OMe CH3.272 " " " " " Me N3.273 " " CO.sub.2Et H OMe OMe CH3.274 " " " " " Cl CH3.275 " " " " Me Me CH3.276 " " " " OMe Me N3.277 " " " " NMe.sub.2 OCH.sub.2 CF.sub.3 N3.278 " " " Me OMe OMe CH3.279 " " " " OMe Me N3.280 " " CO.sub.2 -n-Pr H OMe OMe CH3.281 " " " " " " N3.282 " " " " OMe Me N3.283 " " " " Me Me CH3.284 " " " " OMe Cl CH3.285 " " " Me Me OMe N3.286 " " " " OMe OMe CH3.287 Me COCF.sub.3 CO.sub.2 -i-Pr H OMe OMe CH3.288 " " " " " " N3.289 " " " " OMe Me N3.290 " " " " OMe Cl CH3.291 " " " " Me Me CH3.292 " " " " SMe NEt.sub.2 N3.293 " " CO.sub.2 -i-Pr Me OMe Me N3.294 " " " " OMe OMe CH3.295 Me " CO.sub.2 -Allyl H OMe OMe CH3.296 Et " CO.sub.2Me H OMe OMe CH3.297 " " " H OMe Me N3.298 " " " " Me Me CH3.299 " " " " Cl OMe CH3.300 " " " Me OMe OMe CH3.301 " " " " OMe Me N3.302 " " CO.sub.2Et H OMe OMe CH3.303 " " " " OMe Me CH3.304 " " " " Cl OMe CH3.305 " " " " OMe Me N3.306 " " " Me OMe OMe CH3.307 " " " " " Me N3.308 " " CO.sub.2 -n-Pr H OMe OMe CH3.309 " " " " OMe Me N3.310 " " " " OMe Cl CH3.311 " " " " Me Me CH3.312 " " " Me OMe OMe CH3.313 " " " " OMe Me N3.314 " " CO.sub.2 -i-Pr H OMe OMe CH3.315 " " " " OMe Me N3.316 " " " " Me Me CH3.317 " " " Me OMe Me N3.318 n-Pr COCF.sub.3 CO.sub.2Me H OMe OMe CH3.319 " " " " " Cl CH3.320 " " " " Me Me CH3.321 " " " " OMe Me N3.322 " " " Me OMe OMe CH3.323 " " " " OMe Me N3.324 n-Pr " CO.sub.2Et H " " N3.325 " " " " " OMe CH3.326 " " " " Me Me CH3.327 " " CO.sub.2 -n-Pr " OMe OMe CH3.328 i-Pr " CO.sub.2Me H OMe OMe CH3.329 " " " " OMe Me N3.330 " " " " Me Me CH3.331 " " " " Cl OMe N3.332 " " " Me OMe Me N3.333 " " " " " OMe CH3.334 Allyl " CO.sub.2Me H OMe OMe CH3.335 " " " " " Cl CH3.336 " " " " Me Me CH3.337 " " " " OMe Me N3.338 " " CO.sub.2Et H OMe OMe CH3.339 " " n-Pr " " " CH3.340 " " i-Pr " " " CH3.341 Me COCH.sub.3 CHO " " " CH3.342 " CO.sub.2 CH.sub.3 " " " " CH3.343 " COCH.sub.3 COCH.sub.3 " " " CH3.344 " CO.sub.2 CH.sub.3 " " " " CH3.345 " COCH.sub.3 COS-i-Pr " " " CH3.346 " CO.sub.2 Et " " " " CH3.347 " CHO CONMe.sub.2 " " " CH3.348 " " " " OMe Me N3.349 " COCH.sub.3 " " OMe OMe CH3.350 " " CONH.sub.2 " " " CH3.351 " COCH.sub.3 CSNMe.sub.2 " OMe OMe CH3.352 " CO.sub.2 Et " " " " CH3.353 " COCH.sub.2 CH.sub.3 " " " " CH3.354 " CO.sub.2 Me CSO-i-Pr " " " CH3.355 " CHO " " " " CH3.356 " " C(NNMe.sub.2)H " " " CH3.357 Me COCH.sub.3 C(NOMe)OMe H OMe OMe CH3.358 " CO.sub.2 CH.sub.3 H " " " CH3.359 " CHO " " " " CH3.360 " " C(NOH)H " " " CH3.361 " CO.sub.2 Me " " " " CH3.362 " COCH.sub.3 C(NOMe)H " " " CH3.363 " " CO.sub.2 H " " " CH3.364 " CO.sub.2 Me " " " " CH3.365 " COCH.sub.3 C(NEt)OMe " " " CH3.366 " " C(N-i-Pr)H " " " CH3.367 " CO.sub.2 CH.sub.2 CH.sub.2 Cl COOMe H OMe OMe CH 141-1433.368 " " " H " " CH 123-126__________________________________________________________________________

Number	Name	Date
4632695	Schurter et al.	Dec 1986
4664695	Schurter et al.	May 1987
4892946	Levitt	Jan 1990
4981509	Hillemann	Jan 1991

Number	Date	Country
0001515	May 1983	EPX
0235449	Sep 1987	EPX
0116518	Oct 1987	EPX

Intermediates for the preparation of phenylsulfonylurea herbicides and plant growth regulators

Information

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CPC

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Abstract

Description

Claims

Priority Claims (1)

US Referenced Citations (4)

Foreign Referenced Citations (3)

Non-Patent Literature Citations (2)

Entry
Loev et al, J. Org. Chem., vol. 27 (1962) pp. 2177-2180.
Langmuir, "Formation of Langmuir-Blodgett Films of a Fullerene", 1992, vol. 8, pp. 4-6.