Halogen-containing compounds, herbicidal composition containing the same as an active ingredient, and intermediary compounds therefor

BACKGROUND OF THE INVENTION
1. Field of the Invention
This invention relates to novel halogen-containing compounds, a herbicidal composition containing the same as an active ingredient and intermediary compounds therefor. More specifically, this invention relates to pyrimidine ring or triazine ring-containing halogenated carboxylic acid derivatives, a herbicidal composition, and halogen-containing cycloalkanes useful as an intermediate therefor.
2. Description of the Prior Art
Alkanoic acids containing a pyrimidine ring or triazine ring, and herbicides containing the same as an effective ingredient are proposed, for example, in European Patent No. 346789-A and Japanese Laid-Open Patent Publication No. 85262/90.
However, compounds disclosed in the above known literatures are still not sufficiently satisfying in the points of herbicidal spectrum, the amount of such a compound to be applied, selectivity, etc.

SUMMARY OF THE INVENTION AND DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS OF THE INVENTION
Thus, the present inventors intensely studied for developing compounds having a broader herbicidal spectrum and a higher herbicidal effect than those of the compounds disclosed in the above known literatures, and as a result it was found that halogen-containing compounds wherein the (cyclo) alkanecarboxylic acid (or its derivative) part whose specific position is halogenated and the pyrimidine ring part or triazine ring part having a substituent at the specific position bind through an oxygen atom, sulfur atom or group --OCH.sub.2 -- are novel, and that these compounds exhibit an excellent herbicidal activity on perennial weeds as well as annual weeds and further exhibit high safety on some kinds of cultivation crops.
Thus according to this invention, are provided halogen-containing compounds represented by the following formula (I) and their salts. ##STR2## wherein
X represents a halogen atom,
W represents an oxygen atom, sulfur atom or group --OCH.sub.2 --,
Z.sup.1 and Z .sup.2 each represent a nitrogen atom or group CH, but when Z.sup.1 is a nitrogen atom, Z.sup.2 represents a nitrogen atom or group CH and when Z.sup.1 is a group CH, Z.sup.2 represents a nitrogen atom,
R.sup.1 and R.sup.2 each independently represent either a hydrogen atom, halogen atom or mono- or dilower alkyl-substituted amino, or a lower alkyl, lower alkoxy or lower alkylthio each of which may be substituted with a halogen atom,
R.sup.3 and R.sup.4 each independently represent a hydrogen atom, halogen atom, hydroxycarbonyl, lower alkoxycarbonyl, lower alkyl, lower alkenyl, lower alkynyl, aryl or aralkyl, or R.sup.3 and R.sup.4 form together with the carbon atoms to which they bind respectively a 5- to 8-membered carbon ring or heterocycle and these rings may optionally be substituted with one or the same or different two of hydroxy, lower alkyl, lower alkenyl, alkenyl, lower alkynyl, lower alkoxy, lower alkoxycarbonyl, carbonyl, lower alkylcarbonyloxy and a group=0, and may have unsaturated bond(s) therein,
R.sup.5 represents a hydrogen atom or lower alkyl group, or may form together with part of R.sup.3 a double bond, A represents an oxygen atom, sulfur atom or group=N-B wherein B represents hydroxy or lower alkylcarbonyloxy, or lower alkoxy optionally substituted with hydroxycarbonyl or lower alkoxycarbonyl, and
Y either represents a hydrogen atom, a hydroxy, a mercapto, or
a lower alkoxy, lower alkenoxy, lower alkynoxy, lower alkylthio, aryloxy, aralkyloxy, arylthio, aralkylthio, lower cycloalkoxy, lower cycloalkenyloxy, pyridylthio, furylmethyloxy, furylthio or thienyloxy each optionally substituted with a halogen atom, hydroxy, lower alkyl, lower alkoxy, lower alkylthio, lower alkoxycarbonyl, lower alkylcarbonyl, cyano, nitro or azido, or
an azido, a trilower alkyl-substituted silyloxy or an imidooxy. represents a group ##STR3## wherein
R.sup.6 and R.sup.7 each independently represent a hydrogen atom, lower alkyl, lower alkoxy, aryl or aralkyl, or R.sup.6 and R.sup.7 may form together with the carbon atom to which they bind a lower cycloalkane ring, and
R.sup.8 and R.sup.9 each independently represent a hydrogen atom, a hydroxy, a lower alkyl, a lower alkenyl, a lower alkynyl, a lower alkoxy, a lower alkylcarbonyloxy, a cyano, a lower alkylsulfonyl optionally substituted with a halogen atom, a lower alkyl substituted with lower alkoxycarbonyl, a lower alkyl substituted with hydroxycarbonyl, a lower alkoxy substituted with lower alkoxycarbonyl, a lower alkoxy substituted with hydroxycarbonyl, or
an aryl, aralkyl, aryloxy, aralkyloxy, arylcarbonyloxy, pyridyl, ##STR4## (wherein Z.sup.3 represents an oxygen atom, group CH or sulfur atom, Z.sup.4 represents a nitrogen atom or group CH, Z.sup.1 and Z.sup.2 are as defined above, and m represents an integer of 0 or 1) each optionally substituted with a halogen atom, hydroxy, lower alkyl, lower alkoxy, lower alkyl substituted with halogen atom(s), cyano, nitro, amino, mono- or diloweralkyl-substituted amino or lower alkoxycarbonyl, (wherein R.sup.10 and R.sup.11 each represent a hydrogen atom, a lower alkyl, a lower alkoxycarbonyl, a lower alkyl substituted with lower alkoxycarbonyl, a lower alkyl substituted with hydroxycarbonyl, or an aryl, aralkyl, pyridyl or benzothiazolyl each optionally substituted with a halogen atom, lower alkyl, lower alkyl substituted with a halogen atom, lower alkoxy, cyano, amino or nitro)].
There are described below specific examples of the atom and groups in the definition of X, R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6, R.sup.7, R.sup.8, R.sup.9, R.sup.10, R.sup.11, A and Y in the above general formula (I) of this invention.
Halogen atom
Fluorine, chlorine, bromine or iodine
Lower alkyl group
Lower alkyl group having 5 or less carbon atoms such as, for example, a methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl sec-butyl, tert-butyl, n-pentyl, isopentyl, neopentyl or tert-pentyl group
Lower alkyl group substituted with halogen atom(s)
Lower alkyl group substituted with 1 to 3 halogen atoms such as, for example, a monochloromethyl, a tricloromethyl trifluoromethyl group
Lower alkoxy group
Lower alkoxy group having 5 or less carbon atoms such as, for example, a methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, sec-butoxy or tertbutoxy group
Lower alkoxy group substituted with halogen atom(s)
Lower alkoxy group having 5 or less carbon atoms substituted with 1 to 3 halogen atoms such as, for example, a difluoromethoxy, trifluoromethoxy, 2-chloroethoxy, 2,2-dichloroethoxy, 2,2,2-trichloroethoxy, 2-bromoethoxy, 2-fluoroethoxy, 2,2,2-trifluoroethoxy or 3-bromopropoxy group
Lower alkylthio group
Lower alkylthio group having 5 or less carbon atoms such as, for example, a methylthio, ethylthio, n-propylthio, isopropylthio, n-butylthio, sec-butylthio, isobutylthio or tert-butylthio group
Lower alkylthio group substituted with halogen atom(s)
Lower alkyl thio group having 5 or less carbon atoms substituted with 1 to 3 halogen atoms such as a difluoromethylthio, trifluoromethylthio, 2-chloroethylthio, 2,2-dichloroethylthio, 2,2,2-trichloroethylthio, 2-bromoethylthio, 2-fluoroethylthio, 2,2,2-trifluoroethylthio or 3-bromopropylthio group
Mono- or dilower alkyl-substituted amino group
Mono or dilower alkyl-substituted amino group whose alkyl part has 5 or less carbon atoms such as, for example, a methylamino, ethylamino, n-propylamino, isopropylamino, n-butylamino, sec-butylamino, isobutylamino, tert-butylamino, dimethylamino, diethylamino, di-n-propylamino, diisopropylamino, ethylmethylamino or methylpropylamino group
Lower alkylcarbonyloxy group
Carbonyloxy group to which a lower alkyl group having 5 or less carbon atoms binds such as, for example, a methylcarbonyloxy, ethylcarbonyloxy, n-propylcarbonyloxy, isopropylcarbonyloxy, n-butylcarbonyloxy, isobutylcarbonyloxy, sec-butylcarbonyloxy or tertbutylcarbonyloxy group
Lower alkoxy group substituted with a lower alkoxycarbonyl group
Lower alkoxy group having 5 or less carbon atoms substituted with a carbonyl group to which a lower alkoxy group having 5 or less carbon atoms bind such as, for example, a methoxycarbonylmethoxy, ethoxycarbonylmethoxy, n-propoxycarbonylmethoxy, isopropoxycarbonylmethoxy, n-butoxycarbonylmethoxy, isobutoxycarbonylmethoxy, sec-butoxycarbonylmethoxy, tert-butoxycarbonylmethoxy, 1-methoxycarbonyl-ethoxy, 1-ethoxycarbonylethoxy, 1-n-propoxycarbonyl-ethoxy, 1-isopropoxycarbonylethoxy, 1-n-butoxycarbonyl-ethoxy, 1-isobutoxycarbonylethoxy, 1-sec-butoxycarbonyl-ethoxy or 1-tert-butoxycarbonyl-ethoxy group
Lower alkoxy group substituted with hydroxy
Lower alkoxy group having 5 or less carbon atoms substituted with a hydroxyl group such as, for example, a 2-hydroxyethoxy, 2-hydroxypropoxy, 3-hydroxypropoxy, 2-hydroxybutoxy, 3-hydroxybutoxy or 4-hydroxybutoxy group
Lower alkoxy group substituted with a hydroxycarbonyl group
Lower alkoxy group having 5 or less carbon atoms substituted with a hydroxycarbonyl group such as, for example, a hydroxycarbonylmethoxy or 1-hydroxycarbonyl-ethoxy group
Lower alkoxycarbonyl group
Lower alkoxycarbonyl group whose alkyl part has 5 or less carbon atoms such as, for example, a methoxycarbonyl, ethoxycarbonyl, n-propoxycarbonyl, isopropoxycarbonyl, sec-butoxycarbonyl or tert-butoxycarbonyl group
Lower alkenyl group
Lower alkenyl group having 5 or less carbon atoms such as, for example, an allyl, 2-methyl-2-propenyl, 2-butenyl, 3-butenyl or 3-methyl-2-butenyl group
Lower alkynyl group
Lower alkynyl group having 5 or less carbon atoms such as, for example, a 2-propynyl, 2-butynyl or 3-butynyl group
Lower alkylcarbonyl group
Lower alkylcarbonyl group whose alkyl part has or less carbon atoms such as, for example, a methylcarbonyl, ethylcarbonyl, n-propylcarbonyl, isopropylcarbonyl, n-butylcarbonyl, isobutylcarbonyl, secbutylcarbonyl or tert-butylcarbonyl group
Optionally substituted aryl group
Optionally substituted aryl group such as, for example, a phenyl, 2-methylphenyl, 3-methylphenyl, 4-methylphenyl, 2-chlorophenyl, 3-chlorophenyl, 4-chlorophenyl, 2-bromophenyl, 3-bromophenyl, 4-bromophenyl, 2-fluorophenyl, 3-fluorophenyl, 4-fluorophenyl, 2-nitrophenyl, 3-nitrophenyl, 4-nitrophenyl, 2-methoxyphenyl, 3-methoxyphenyl, 4-methoxyphenyl, 2-trifluoromethylphenyl, 3-trifluoromethylphenyl, 4-trifluoromethylphenyl, 2-aminophenyl, 3-aminophenyl, 4-aminophenyl, 2-hydroxyphenyl, 3-hydroxyphenyl, 2,3-dimethylphenyl, 2,4-dimethylphenyl, 2,5-dimethylphenyl, 2,6-dimethylphenyl, 3,4-dimethylphenyl, 3,5-dimethylphenyl, 2,3-dichlorophenyl, 2,4-dichlorophenyl, 2,5-dichlorophenyl, 2,6-dichlorophenyl, 3,4-dichlorophenyl, 3,5-dichlorophenyl, 2,4-dinitrophenyl, 2,6-dinitrophenyl, 3,4-dinitrophenyl, 3,5-dinitrophenyl, 2,3,5-trichlorophenyl, 2,4,6-trichlorophenyl, 1-naphthyl or 2-naphthyl group
Optionally substituted aralkyl group
Optionally substituted aralkyl group such as, for example, a benzyl, 2-bromobenzyl, 3-bromobenzyl, 4-bromobenzyl, 2-chlorobenzyl, 3-chlorobenzyl, 4-chlorobenzyl, 2-fluorobenzyl, 3-fluorobenzyl, 4-fluorobenzyl, 2-methoxybenzyl, 3-methoxybenzyl, 4-methoxybenzyl, 2-methylbenzyl, 3-methylbenzyl, 4-methylbenzyl, 2-nitrobenzyl, 3-nitrobenzyl or 4-nitrobenzyl group
Lower alkenyloxy group
Lower alkenyloxy group having 5 or less carbon atoms such as, for example, a vinyloxy, allyloxy, 3-butenyloxy, 1-methyl-2-propenoxy or 2-methyl-2-propenyloxy group
Lower alkynyloxy group
Lower alkynyloxy group having 5 or less carbon atoms such as, for example, a 2-propynyloxy, 1-methyl-2-propynyloxy, 2-butynyloxy or 3-butynyloxy group
Optionally substituted aryloxy group
Optionally substituted aryloxy group such as, for example, a phenoxy, naphthoxy, 2-bromophenoxy, 3-chlorophenoxy, 4-chlorophenoxy, 2-methylphenoxy, 3-bromophenoxy, 4-bromophenoxy, 2-chlorophenoxy, 3-methylphenoxy, 4-methylphenoxy, 2-methoxyphenoxy, 3-methoxyphenoxy, 4-methoxyphenoxy, 2-nitrophenoxy, 3-nitrophenoxy of 4-nitrophenoxy group
Optionally substituted aralkyloxy group
Optionally substituted aralkyloxy group such as, for example, a benzyloxy, 2-bromobenzyloxy, 3-bromobenzyloxy, 4-bromobenzyloxy, 2-chlorobenzyloxy, 3-chlorobenzyloxy, 4-chlorobenzyloxy, 2-fluorobenzyloxy, 3-fluorobenzyloxy, 4-fluorobenzyloxy, 2-methoxybenzyloxy, 3-methoxybenzyloxy, 4-methoxybenzyloxy, 2-methylbenzyloxy, 3-methylbenzyloxy, 4-methylbenzyloxy, 2-nitrobenzyloxy, 3-nitrobenzyloxy, 4-nitrobenzyloxy, 2,4-dinitrobenzyloxy, 3,4-dinitrobenzyloxy,3,5-dinitrobenzyloxy or 2,4,6-trimethylbenzyloxy group
Optionally substituted arylthio group
Optionally substituted arylthio group such as, for example a phenylthio, 2-bromophenylthio, 3-bromophenylthio, 4-bromophenylthio, 2-chlorophenylthio, 3-chlorophenylthio, 4-chlorophenylthio, 4-fluorophenylthio, 2-methoxyphenylthio, 3-methoxyphenylthio, 4-methoxyphenylthio, 4-methylphenylthio or 4-nitrophenylthio group
Optionally substituted aralkylthio group
Optionally substituted aralkyl thio group such as, for example, a benzylthio, 2-, 3- or 4-bromobenzylthio, 2-,3- or 4-chlorobenzylthio, 2-, 3- or 4-fluorobenzylthio, 2-, 3- or 4-methoxybenzylthio, 2-, 3- or 4-methylbenzylthio, or 3- or 4-nitrobenzylthio group
Optionally substituted pyridylthio group
Optionally substituted pyridylthio group such as, for example, a pyridyl-2-thio or 5-nitropyridyl2-thio
Lower cycloalkoxy group
For example, a cyclopropyloxy, cyclobutoxy, cyclopentyloxy or cyclohexyloxy group
Lower cycloalkenyloxy group
For example, a 2-cyclopentenyloxy, 2-cyclohexenyloxy or 3-cyclohexenyloxy group
Furylmethyloxy group
For example, a 2-furylmethyloxy or 3-furylmethyloxy group
Furylmethylthio group
For example, a 2-furylmethylthio or 3-furylmethylthio group
Thienylmethyloxy group
For example, a 2-thienylmethyloxy or 3-thienylmethyloxy group
Lower alkylsulfonyl group optionally substituted with halogen atom(S)
Lower alkylsulfonyl group having 5 or less carbon atoms optionally substituted with 1 to 3 halogen atoms such as, for example, a methanesulfonyl, ethanesulfonyl, 1-propanesulfonyl, 2-propanesulfonyl, 1-butanesulfonyl, trichloromethanesulfonyl, trifluoromethanesulfonyl or 2,2,2-trifluoromethanesulfonyl group
5- to 8- membered carbon ring or heterocycle ring optionally containing hetero atom(s)
Carbon ring or heterocycle ring such as, for example a cyclopentane ring, cyclohexane ring, cycloheptane ring, cyclooctane ring, cyclopentene ring, cyclohexene ring, cyclooctane ring, tetrahydrofuran ring, tetrahydropyran ring, thiolane ring, thiane ring, pyrrolidine or piperidine ring
Optionally substituted arylcarbonyloxy group
Optionally substituted arylcarbonyloxy group such as, for example, a phenylcarbonyloxy, 2-chlorophenylcarbonyloxy, 3-chlorophenylcarbonyloxy, 4-chlorophenylcarbonyloxy, 2-trifluoromethylphenylcarbonyloxy, 3-trifluoromethylphenylcarbonyloxy, 4-trifluoromethylphenylcarbonyloxy, 2,4-dichlorophenylcarbonyloxy, 2,6-dichlorophenylcarbonyloxy, 3,4-dichlorophenylcarbonyloxy, 3,5-dichlorophenylcarbonyloxy or 2,4-dichloro-3-methylphenylcarbonyloxy group
Optionally substituted benzothiazolyl group
Optionally substituted benzothiazonyl group such as, for example, a benzothiazol-2-yl or 6-nitrobenzothiazol-2-yl group
Groups not specifically mentioned as examples of the above groups can be selected by optioned combination based on the above atoms and groups or according to the common sense of this field.
When Y in the above formula (I) of the invention is a hydroxyl group, its salts are included in the compounds of the invention. Preferably, its salts are usually agriculturally acceptable salts, and examples thereof are alkali metal, ammonium and lower alkylammonium salts such as sodium, potassium, ammonium, isopropylammonium, triethylammonium salts.
One of the characteristics of the halogen-containing compounds of this invention is that X in the formula (I) is a halogen atom. Due to the fact that X is a halogen atom, the compounds of the invention have a stronger herbicidal activity than the compounds wherein X is a hydrogen atom.
Although X in the formula (I) represents a fluorine atom, chlorine atom, bromine atom or iodine atom, X is preferably a fluorine atom or chlorine atom, most preferably a fluorine atom.
Another characteristic of the compounds of the invention is that the compounds have a group ##STR5## This group can specifically be classified into the following three groups: ##STR6## Among these three groups, preferred are ##STR7## and particularly preferred is ##STR8##
Atoms or groups preferred as R.sup.1 and R.sup.2 in the above three groups vary depending on whether the skeleton is pyrimidine or tryazine. Namely in case of ##STR9## it is preferred that either both R.sup.1 and R.sup.2 are lower alkoxy, R.sup.1 is lower alkoxy and R.sup.2 is a halogen atom, or R.sup.1 is a halogen atom and R.sup.2 is lower alkoxy. In case of ##STR10## it is preferred that both R.sup.1 and R.sup.2 are lower alkoxy. Further, in case of ##STR11## it is preferred that R.sup.1 is lower alkylthio and R.sup.2 is a halogen atom particularly a chlorine atom.
Preferred as the compounds of the invention are those wherein R.sup.3 and R.sup.4 in the formula (I) are each independently lower alkyl, lower alkenyl, lower alkynyl or aralkyl, or R.sup.3 and R.sup.4 combine to form a cyclopentane ring or cyclohexane ring. Further, it is preferred that A in the general formula (I) is an oxygen atom or sulfur atom rather than a group=N-B.
Further, it is preferred that W is an oxygen atom or sulfur atom among an oxygen atom, sulfur atom and group --OCH.sub.2 --, and an oxygen atom is particularly preferred.
It is most preferred that R.sup.5 is a hydrogen atom.
Further, Y is preferably hydroxy, mercapto, lower alkoxy, lower alkenyloxy, lower alkynyloxy, a group ##STR12## (wherein R.sup.6 and R.sup.7 are as defined in the formula (I)) or a group ##STR13## (wherein either R.sup.8 and R.sup.9 is a hydrogen atom), particularly preferably hydroxy, lower alkoxy, lower alkenyloxy, lower alkynyloxy or a group ##STR14## (wherein R.sup.6 and R.sup.7 are as defined in the formula (I)),
Preferred examples of the halogen-containing compounds of the invention represented by the formula (I) are set forth in the following (1) to (6).
(1) Halogen-containing compounds represented by the following formula (I)-i ##STR15## wherein R.sup.1, R.sup.2, R.sup.3, R.sup.4, X, Y and W are as defined in the general formula (I)
(2) Halogen-containing compounds represented by the following (I)-ii ##STR16## wherein R.sup.1, R.sup.2, R.sup.3, R.sup.4, X, Y and W are as defined in the formula (I)
(3) Halogen-containing compounds represented by the following general formula (I)-iii ##STR17## wherein R.sup.1, R.sup.2, R.sup.3, R.sup.4, X, Y and W are as defined in the formula (I)
(4) Halogen-containing compounds represented by the following general formula (I)-iv ##STR18## wherein R.sup.1, R.sup.2, Z.sup.1, Z.sup.2, X, Y and W are as defined in the general formula (I), and R.sup.3' and R.sup.4' form together with the carbon atoms to which they bind a 5- to 8-membered carbon ring or heterocycle optionally containing hetero atom(s), and these rings may optionally be substituted with one or the same or different two of hydroxy, lower alkyl, lower alkylthio, lower alkanyl, lower alkynyl, lower alkoxy, lower alkoxycarbonyl, lower alkylcarbonyloxy and a group=0
(5) Halogen-containing compounds represented by the following formula (I)-v ##STR19## wherein R.sup.1, R.sup.2, Z.sup.1, Z.sup.2, X, Y and W are as defined in the formula (I), and n represents 0, 1, 2 or 3
(6) Halogen-containing compounds represented by the following formula (I)-vi ##STR20## wherein R.sup.1, R.sup.2, Y and W are as defined in the formula (I), and R.sup.3" and R.sup.4" each independently represent a hydrogen atom, halogen atom, hydroxycarbonyl, lower alkoxycarbonyl, lower alkyl, lower alkenyl, lower alkynyl, aryl or aralkyl.
In the compounds of the formula (I)-vi, it is preferred that R.sup.3" and R.sup.4" are each independently a lower alkyl, lower alkenyl, lower alkynyl or aralkyl.
According to the researches by the present inventors, it was found that halogen-containing compounds represented by the above general formula (I) are novel and have a strong herbicidal activity on many kinds of weeds.
Thus according to this invention is provided a herbicidal composition which comprises a halogen-containing compound represented by the formula (I) as an active ingredient and agriculturally and horticulturally acceptable diluent(s) or carrier(s).
Further according to this invention is provided a method for exterminating weeds or preventing the generation or growth of weeds.
The herbicide composition and its application method of the invention are detailedly described later.
According to the investigation by the present inventors, it was revealed that the halogen-containing cyclic compounds of the following formula (II) are novel which can become part of the synthetic intermediates of the halogen-containing compounds of this invention having a herbicidal activity. These halogen-containing cyclic compounds (II) are encompassed in the invention, too.
Namely, according to this invention are provided halogen-containing cyclic compounds represented by the following formula (II) ##STR21## wherein
X, A and Y are as defined in the formula (I),
W' represents an oxygen atom or sulfur atom,
R.sup.3' and R.sup.4' form together with the carbon atoms to which they bind respectively a 5- to 8-membered carbon ring or heterocyclic ring optionally containing hetero atom(s), and these rings may optionally be substituted with one or the same or different two of hydroxy, lower alkyl, lower alkenyl, lower alkynyl, lower alkoxy, lower alkoxycarbonyl, lower alkylcarbonyloxy and a group=0, and may unsaturated bond(s) therein,
R.sup.5 represents a hydrogen atom or lower alkyl group, or R.sup.5 may form together with part of R.sup.3 a double bond, and
V represents a hydrogen atom, a lower alkyl, a lower alkylcarbonyl, a lower alkylsulfonyl or an aralkyl, arylcarbonyl or arylsulfonyl each optionally substituted with a halogen atom, hydroxy, nitro, cyano, lower alkyl, lower alkoxy, halogen-substituted lower alkyl, halogen-substituted lower alkoxy, amino, or mono- or dilower alkyl-substituted amino.
The halogen-containing cyclic compounds of the invention represented by the formula (II) have their characteristics in that they have a halogen atom as X and R.sup.3' and R.sup.4' may form together with the carbon atoms to which they bind a 5- to 8-membered carbon ring or heterocycle optionally containing hetero atom(s).
In the formula (II) X is a fluorine atom, chlorine atom, bromine atom or iodine atom, preferably a fluorine atom or chlorine atom, particularly preferably a fluorine atom.
Specific examples of the 5- to 8-membered carbon ring or heterocycle which R.sup.3' and R.sup.4' combine to form are a cyclopentane ring, a cyclohexane ring, a cycloheptane ring, a cyclooctane ring, a cyclopentene ring, a cyclohexene ring, cycloheptene ring, a cyclooctene ring, a tetrahydrofuran ring, a tetrahydropyran ring a thiolane ring, a thiane ring, a pyrrolidine ring, a piperidine ring, etc., but the cyclopentane ring and cyclohexane ring are particularly preferred among them.
Further in the formula (II), A, Y and R.sup.5 are as defined in the formula (I), and the abovementioned preferred ones in the general formula (I) are likewise preferred.
Further in the formula (II) W' is an oxygen atom or sulfur atom and an oxygen atom is preferred.
Further in the formula (II) V is a hydrogen atom, lower alkyl, lower alkylcarbonyl, lower alkyl-sulfonyl aralkyl, arylcarbonyl or arylsulfonyl. The aromatic nucleus of the aralkyl, arylcarbonyl, and arylsulfonyl among them may optionally be substituted with at least one of halogen atom(s), hydroxy, nitro, cyano, lower alkyl, lower alkoxy, halogen-substituted lower alkyl, halogen-substituted lower alkoxy, amino and mono- or dilower alkyl-substituted amino. Preferred as V are a hydrogen atom, aralkyl and arylcarbonyl.
Preferred examples of the compounds of the invention represented by the formula (II) include halogen-containing cyclic compounds represented by the following formula (II)-1 ##STR22## wherein X, Y, W' and V are as defined in the formula (II), and n represents 0, 1, 2 or 3, preferably 0 or 1.
The compound of this invention may exist a number of different stereoisomeric forms according to a number of asymmetric carbon(s). For example, when two carbon atoms to which R.sup.3 and R.sup.4 bind respectively are both the asymmetric carbons, the compound of this invention may include four stereoisomeric forms (cisform, trans-form erythro-form or threo-form) about its two asynmetric carbons. And, further, these isomers may include a dextrorotatory, levorotatory or racemie form.
It should be understood the compound of this invention encompasses all these stereoisomers.
Specific compounds included in the halogen-containing compounds of the invention represented by the formula (I) are examplified in Tables 1 to 7. NMR analysis values and/or physical data measured on some of the halogen-containing compounds are shown in Tables 8 to 13.
Specific compounds included in the halogen-containing cyclic compounds of the invention represented by the formula (II) are examplified in Tables 14 to 15. NMR analysis value and/or physical data measured on some of the halogen-containing cyclic compounds are shown in Table 16.
The meanings of the abbreviations in Tables 1 to 7 and Tables 14 to 15 are as follows.
Ph means a phenyl group.
Ph in Ph-2Cl, Ph-2-OCH.sub.3, Ph-2NO.sub.2, Ph-2-OC.sub.2 H.sub.5 Ph-2CF.sub.3, Ph-3Cl, Ph-3-OCH.sub.3, Ph-3NO.sub.2, Ph-3-OC.sub.2 H.sub.5, Ph-3CF.sub.3, Ph-4Cl, Ph-4-OCH , Ph-4NO.sub.2, Ph-4-OC.sub.2 H.sub.5, Ph-4CF.sub.3, Ph-2Br, Ph-2CH.sub.3, Ph-3Br, Ph-3CH.sub.3, Ph-4Br, Ph-4CH.sub.3, etc. means a phenyl group, the figure part in the "2Cl" etc. following Ph means the substitution position on the phenyl ring, and Cl, OCH.sub.3, NO.sub.2, OC.sub.2 H.sub.5, CF.sub.3, Br, CH.sub.3, etc. mean substituents at the substition position.
Ph-2,4-DiCl means a 2,4-dichlorophenyl group, Ph-2,6-DiCl means a 2,6-dichlorophenyl group, Ph-3,4-DiCl means a 3,4-dichlorophenyl group and Ph-3,5-DiCl means a 3,5-dichlorophenyl group.
Ph-2,4 DiCl-3CH.sub.3 means a 2,4-dichloro-3-methylphenyl group.
Succinimidyl means a 2,5-dioxo-1-pyrrolidinyl group.
O--N.dbd.C(--(C.sub.2 H.sub.5).sub.5 --) means a group ##STR23## and C(--(C.sub.2 H.sub.5 --) means a cyclohexyl group.
The 2-thiadiazolyl of NH-2-thiadiazolyl means a 1,3,4-thiadiazol-2-yl group and the 2-thiadiazolvl-5-CF.sub.3 in NH-2-thiadiazolyl-5-CF.sub.3 means a 5-trifluoromethyl1,3,4-thiadiazol-2-yl group
Cis, trans, erythro or threo means relative configuration about two substituents located at two adjacent asymmetric carbons of the corresponding compound.
Rac, + or - means racemic, dextrorotatory or levorotatory form respectively.
Mixture means mixture of racemic storeoisomers.
Further, the expressions such as axial methyl group, equatorial methyl group and equatorial t-butyl group in the compound Nos. 1276a to 1295a in Table 8 mean the orientation of each alkyl group when these alkyl groups exist on the ring of the respective compounds. ##STR24##
TABLE 3 Compound No. R.sup.3 R.sup.4 W Y Q R.sup.1 R.sup.2 Remarks 3001 (CH.sub.2).sub.3 O H Q.sub.2 OCH.sub.3 OCH.sub.3 3002 (CH.sub.2).sub.3 O OH Q.sub.2 OCH.sub.3 OCH.sub.3 3003a (CH.sub.2).sub.3 O OCH.sub.3 Q.sub.2 O CH.sub.3 OCH.sub.3 cis 3003b (CH.sub.2).sub.3 O OCH.sub.3 Q.sub.2 OCH.sub.3 OCH.sub.3 trans 3004 (CH.sub.2).sub.3 O OC.sub.2 H.sub.5 Q.sub.2 OCH.sub.3 OCH.sub.3 3005 (CH.sub.2).sub.3 O O-n-C.sub.3 H.sub.7 Q.sub.2 C OH.sub.3 OCH.sub.3 3006 (CH.sub.2).sub.3 O O-i-C.sub.3 H.sub.7 Q.sub.2 OCH.sub.3 OCH.sub.3 3007 (CH.sub.2).sub.3 O O-n-C.sub.4 H.sub.9 Q.sub.2 C OH.sub.3 OCH.sub.3 3008 (CH.sub.2).sub.3 O O-i-C.sub.4 H.sub.9 Q.sub.2 OCH.sub.3 OCH.sub.3 3009 (CH.sub.2).sub.3 O O-s-C.sub.4 H.sub.9 Q.sub.2 C OH.sub.3 OCH.sub.3 3010 (CH.sub.2).sub.3 O O-t-C.sub.4 H.sub.9 Q.sub.2 OCH.sub.3 OCH.sub.3 3011 (CH.sub.2).sub.3 O O(CH.sub.2).sub.2Cl Q.sub.2 C OH.sub.3 OCH.sub.3 3012 (CH.sub.2).sub.3 O OCH.sub.2 SCH.sub.3 Q.sub.2 OCH.sub.3 OCH.sub.3 3013 (CH.sub.2).sub.3 O OCH.sub.2Ph Q.sub.2 OCH.sub.3 OCH.sub.3 3014 (CH.sub.2).sub.3 O OPh Q.sub.2 OCH.sub.3 OCH.sub.3 3015 (CH.sub.2).sub.3 O OPh-2Cl Q.sub.2 OCH.sub.3 OCH.sub.3 3016 (CH.sub.2).su b.3 O OCH.sub.2CHCH.sub.2 Q.sub.2 OCH.sub.3 OCH.sub.3 3017 (CH.sub.2).sub .3 O OCH.sub.2CCH Q.sub.2 OCH.sub.3 OCH.sub.3 3018 (CH.sub.2).sub.3 O OCH.sub.2OC.sub.2 H.sub.5 Q.sub.2 OCH.sub.3 OCH.sub.3 3019 (CH.sub.2).sub.3 O H Q.sub.2 Cl OCH.sub.3 3020 (CH.sub.2).sub.3 O OH Q.sub.2 Cl OCH.sub.3 3021 (CH.sub.2).sub.3 O OCH.sub.3 Q.sub.2 Cl OCH.sub.3 3022 (CH.sub.2).sub.3 O OC.sub. 2 H.sub.5 Q.sub.2 Cl OCH.sub.3 3023 (CH.sub.2).sub.3 O O-n-C.sub.3 H.sub.7 Q.sub.2 Cl OCH.sub.3 3024 (CH.sub.2).sub.3 O O-i-C.sub.3 H.sub.7 Q.sub.2 Cl OCH.sub.3 3025 (CH.sub.2).sub.3 O O-n-C.sub.4 H.sub.9 Q.sub.2 Cl OCH.sub.3 3026 (CH.sub.2).sub.3 O O-i-C.sub.4 H.sub.9 Q.sub.2 Cl OCH.sub.3 3027 (CH.sub.2).sub.3 O O-s-C.sub.4 H.sub.9 Q.sub.2 Cl OCH.sub.3 3028 (CH.sub.2).sub.3 O O-t-C.sub.4 H.sub.9 Q.sub.2 Cl OCH.sub.3 3029 (CH.sub.2).sub.3 O O(CH.sub.2).sub.2Cl Q.sub.2 Cl OCH.sub.3 3030 (CH.sub.2).sub.3 O OCH.sub.2SCH.sub.3 Q.sub.2 Cl OCH.sub.3 3031 (CH.sub.2).sub.3 O OCH.sub.2P h Q.sub.2 Cl OCH.sub.3 3032 (CH.sub.2).sub.3 O OPh Q.sub.2 Cl OCH.sub.3 3033 (CH.sub.2).sub.3 O O Ph-2Cl Q.sub.2 Cl OCH.sub.3 3034 (CH.sub.2).sub .3 O OCH.sub.2CHCH.sub.2 Q.sub.2 Cl OCH.sub.3 3035 (CH.sub.2).sub.3 O OCH.sub.2CCH Q.sub.2 Cl OCH.sub.3 3036 (CH.sub.2).sub.3 O OCH.sub.2OC.sub .2 H.sub.5 Q.sub.2 Cl OCH.sub.3 3037 (CH.sub.2).sub.3 O H Q.sub.2 OCH.sub.3 OC.sub.2 H.sub.5 3038 (CH.sub.2).sub.3 O OH Q.sub.2 OCH.sub.3 C O.sub.2 H.sub.5 3039 (CH.sub.2).sub.3 O OCH.sub.3 Q.sub.2 OCH.sub.3 OC.sub.2 H.sub.5 3040 (CH.sub.2).sub.3 O OC.sub.2 H.sub.5 Q.sub.2 OCH.sub.3 OC.sub.2 H.sub.5 3041 (CH.sub.2).sub.3 O O-n-C.sub.3 H.sub.7 Q.sub.2 OCH.sub.3 OC.sub.2 H.sub.5 3042 (CH.sub.2).sub.3 O O-i-C.sub.3 H.sub.7 Q.sub.2 OCH.sub.3 OC.sub. 2 H.sub.5 3043 (CH.sub.2).sub.3 O O-n-C.sub.4 H.sub.9 Q.sub.2 OCH.sub.3 OC.sub.2 H.sub.5 3044 (CH.sub.2).sub.3 O O-i-C.sub.4 H.sub.9 Q.sub.2 OCH.sub.3 OC.sub.2 H.sub.5 3045 (CH.sub.2).sub.3 O O-s-C.sub.4 H.sub.9 Q.sub.2 OCH.sub.3 OC.sub.2 H.sub.5 3046 (CH.sub.2).sub.3 O O-t-C.sub.4 H.sub.9 Q.sub.2 OCH.sub.3 OC.sub.2 H.sub.5 3047 (CH.sub.2).sub.3 O O(CH.sub.2).sub.2Cl Q.sub.2 OCH.sub.3 OC.sub.2 H.sub.5 3048 (CH.sub.2).sub.3 O OCH.sub.2SCH.sub.3 Q.sub.2 OCH.sub.3 OC.sub.2 H.sub.5 3049 (CH.sub.2).sub.3 O OCH.sub.2Ph Q.sub.2 OCH.sub.3 OC.sub.2 H.sub.5 3050 (CH.sub.2).sub.3 O OPh Q.sub.2 OCH.sub.3 OC.sub.2 H.sub.5 3051 (CH.sub.2).sub.3 O OPh-2Cl Q.sub.2 OCH.sub.3 OC.sub.2 H.sub. 5 3052 (CH.sub.2).sub.3 O OCH.sub.2CHCH.sub.2 Q.sub.2 OCH.sub.3 OC.sub.2 H.sub.5 3053 (CH.sub.2).sub.3 O OCH.sub.2CCH Q.sub.2 C OH.sub.3 OC.sub.2 H.sub.5 3054 (CH.sub.2).sub.3 O OCH.sub.2OC.sub.2 H.sub.5 Q.sub.2 OCH.sub.3 OC.sub.2 H.sub.5 3055 (CH.sub.2).sub.3 O H Q.sub.2 OC.sub.2 H.sub.5 OC.sub.2 H.sub.5 3056 (CH.sub.2).sub.3 O OH Q.sub.2 OC.sub.2 H.sub.5 OC.sub.2 H.sub.5 3057 (CH.sub.2).sub.3 O OCH.sub.3 Q.sub.2 OC.sub.2 H.sub.5 OC.sub.2 H.sub.5 3058 (CH.sub.2).sub.3 O OC.sub.2 H.sub.5 Q.sub.2 OC.sub.2 H.sub.5 OC.sub.2 H.sub.5 3059 (CH.sub.2).sub.3 O O-n-C.sub.3 H.sub.7 Q.sub.2 OC.sub.2 H.sub.5 OC.sub.2 H.sub.5 3060 (CH.sub. 2).sub.3 O O-i-C.sub.3 H.sub.7 Q.sub.2 OC.sub.2 H.sub.5 OC.sub.2 H.sub.5 3061 (CH.sub.2).sub.3 O O-n-C.sub.4 H.sub.9 Q.sub.2 OC.sub.2 H.sub.5 OC.sub.2 H.sub.5 3062 (CH.sub.2).sub.3 O O-i-C.sub.4 H.sub.9 Q.sub.2 OC.sub.2 H.sub.5 OC.sub.2 H.sub.5 3063 (CH.sub.2).sub.3 O O-s-C.sub.4 H.sub.9 Q.sub.2 OC.sub.2 H.sub.5 OC.sub.2 H.sub.5 3064 (CH.sub.2).sub.3 O O-t-C.sub.4 H.sub.9 Q.sub.2 OC.sub.2 H.sub.5 OC.sub.2 H.sub.5 3065 (CH.sub.2).sub.3 O O(CH.sub.2).sub.2Cl Q.sub.2 OC.sub.2 H.sub.5 OC.sub.2 H.sub.5 3066 (CH.sub.2).sub.3 O OCH.sub.2SCH.sub.3 Q.sub.2 OC.sub.2 H.sub.5 OC.sub.2 H.sub.5 3067 (CH.sub.2).sub.3 O OCH.sub.2Ph Q.sub.2 OC.sub.2 H.sub.5 OC.sub.2 H.sub.5 3068 (CH.sub.2).sub.3 O OPh Q.sub.2 OC.sub.2 H.sub.5 OC.sub.2 H.sub.5 3069 (CH.sub.2).sub.3 O OPh-2Cl Q.sub.2 OC.sub.2 H.sub.5 OC.sub.2 H.sub.5 3070 (CH.sub.2).sub.3 O OCH.sub.2CHCH.sub.2 Q.sub.2 OC.sub.2 H.sub.5 OC.sub.2 H.sub.5 3071 (CH.sub.2).sub.3 O OCH.sub.2CCH Q.sub.2 OC.sub.2 H.sub.5 OC.sub.2 H.sub.5 3072 (CH.sub.2).sub.3 O OCH.sub.2OC.sub.2 H.sub.5 Q.sub.2 OC.sub.2 H.sub.5 OC.sub.2 H.sub.5 3073 (CH.sub.2).sub.3 O OCH.sub.2CCH Q.sub.2 OCH.sub.3 OC.sub.2 H.sub.5 3074 (CH.sub.2).sub.3 O OCH.sub.2OC.sub.2 H.sub.5 Q.sub.2 OCH.sub.3 OC.sub.2 H.sub.5 3075 (CH.sub.2).sub.3 O H Q.sub.3 SCH.sub.3 Cl 3076 (CH.sub.2).sub.3 O OH Q.sub.3 SCH.sub.3 Cl 3077a (CH.sub.2).sub. 3 O OCH.sub.3 Q.sub.3 SCH.sub.3 Cl cis 3077b (CH.sub.2).sub.3 O OCH.sub.3 Q.sub.3 SCH.sub.3 Cl trans 3078 (CH.sub.2).sub.3 O OC.sub.2 H.sub.5 Q.sub.3 SCH.sub.3 Cl 3079 (CH.sub.2).sub.3 O O-n-C.sub.3 H.sub.7 Q.sub.3 SCH.sub.3 Cl 3080 (CH.sub.2).sub.3 O O-i-C.sub.3 H.sub.7 Q.sub.3 SCH.sub.3 Cl 3081 (CH.sub.2).sub.3 O O-n-C.sub.4 H.sub.9 Q.sub.3 SCH.sub.3 Cl 3082 (CH.sub.2).sub.3 O O-i-C.sub.4 H.sub.9 Q.sub.3 SCH.sub.3 Cl 3083 (CH.sub.2).sub.3 O O-s-C.sub.4 H.sub.9 Q.sub.3 SCH.sub.3 Cl 3084 (CH.sub.2).sub.3 O O-t-C.sub.4 H.sub.9 Q.sub.3 SCH.sub.3 Cl 3085 (CH.sub.2).sub.3 O O(CH.sub.2).sub.2Cl Q.sub.3 SCH.sub.3 Cl 3086 (CH.sub.2 ).sub.3 O OCH.sub.2SCH.sub.3 Q.sub.3 SCH.sub.3 Cl 3087 (CH.sub.2).sub.3 O OCH.sub.2Ph Q.sub.3 SCH.sub.3 Cl 3088 (CH.sub.2).sub.3 O OPh Q.sub.3 SCH.sub.3 Cl 3089 (CH.sub.2).sub.3 O OPh-2Cl Q.sub.3 SCH.sub.3 Cl 3090 (CH.sub.2).sub.3 O OCH.sub.2CHCH.sub.2 Q.sub.3 SCH.sub.3 Cl 3091 (CH.sub.2).sub.3 O OCH.sub.2CCH Q.sub.3 SCH.sub.3 Cl 3092 (CH.sub.2).sub.3 O OCH.sub.2OC.sub.2 H.sub.5 Q.sub.3 SCH.sub.3 Cl 3093 (CH.sub.2).sub.3 O H Q.sub.3 SCH.sub.3 OCH.sub.3 3094a ( CH.sub.2).sub.3 O OH Q.sub.3 SCH.sub.3 OCH.sub.3 cis 3094b (CH.sub.2).sub .3 O OH Q.sub.3 SCH.sub.3 OCH.sub.3 trans 3095a (CH.sub.2).sub.3 O OC.sub.2 H.sub.5 Q.sub.3 SCH.sub.3 OCH.sub.3 cis 3095b (CH.sub.2).sub.3 O OC.sub.2 H.sub.5 Q.sub.3 SCH.sub.3 OCH.sub.3 trans 3096 (CH.sub.2).sub.3 O O-n-C.sub.3 H.sub.7 Q.sub.3 SCH.sub.3 OCH.sub.3 3097 (CH.sub.2).sub.3 O O-i-C.sub.3 H.sub.7 Q.sub.3 SCH.sub.3 OCH.sub.3 3098 (CH.sub.2).sub.3 O O-n-C.sub.4 H.sub.9 Q.sub.3 SCH.sub.3 OCH.sub.3 3099 (CH.sub.2).sub.3 O O-i-C.sub.4 H.sub.9 Q.sub.3 SCH.sub.3 OCH.sub.3 3100 (CH.sub.2).sub.3 O O-s-C.sub.4 H.sub.9 Q.sub.3 SCH.sub.3 OCH.sub.3 3101 (CH.sub.2).sub.3 O O-t-C.sub.4 H.sub.9 Q.sub.3 SCH.sub.3 OCH.sub.3 3102 (CH.sub.2).sub.3 O ( OCH.sub.2).sub.2Cl Q.sub.3 SCH.sub.3 OCH.sub.3 3103 (CH.sub.2).sub.3 O OCH.sub.2 SCH.sub.3 Q.sub.3 SCH.sub.3 OCH.sub.3 3104 (CH.sub.2).sub.3 O OCH.sub.2Ph Q.sub.3 SCH.sub.3 OCH.sub.3 3105 (CH.sub.2).sub.3 O OPh Q.sub.3 SCH.sub.3 OCH.sub.3 3106 (CH.sub.2).sub.3 O OPh-2Cl Q.sub.3 SCH.sub.3 OCH.sub.3 3107 (CH.sub.2).sub.3 O OCH.sub.2CHCH.sub.2 Q.sub.3 C SH.sub.3 OCH.sub.3 3108 (CH.sub.2).sub.3 O OCH.sub.2CCH Q.sub.3 SCH.sub.3 OCH.sub.3 3109 (CH.sub.2).sub.3 O OCH.sub.2OC.sub.2 H.sub.5 Q.sub.3 SCH.sub.3 OCH.sub.3 3110 (CH.sub.2).sub.3 O H Q.sub.3 SO.sub.2 CH.sub.3 Cl 3111 (CH.sub.2).sub.3 O OH Q.sub.3 SO.sub.2 CH.sub.3 Cl 3112 (CH.sub.2).sub.3 O OCH.sub.3 Q.sub.3 SO.sub.2 CH.sub.3 Cl 3113 (CH.sub.2).sub.3 O OC.sub.2 H.sub.5 Q.sub.3 SO.sub.2 CH.sub.3 Cl 3114 (CH.sub.2).sub.3 O O-n-C.sub.3 H.sub.7 Q.sub.3 SO.sub.2 CH.sub.3 Cl 3115 (CH.sub.2).sub.3 O O-i-C.sub.3 H.sub.7 Q.sub.3 SO.sub.2 CH.sub.3 Cl 3116 (CH.sub.2).sub.3 O O-n-C.sub.4 H.sub.9 Q.sub.3 SO.sub.2 CH.sub.3 Cl 3117 (CH.sub.2).sub.3 O O-i-C.sub.4 H.sub.9 Q.sub.3 SO.sub.2 CH.sub.3 Cl 3118 (CH.sub.2).sub.3 O O-s-C.sub.4 H.sub.9 Q.sub.3 SO.sub.2 CH.sub.3 Cl 3119 (CH.sub.2).sub.3 O O-t-C.sub.4 .sub.9 Q.sub.3 SO.sub.2 CH.sub.3 Cl 3120 (CH.sub.2).sub.3 O O(CH.sub.2).sub.2Cl Q.sub.3 SO.sub.2 CH.sub.3 Cl 3121 (CH.sub.2).sub.3 O OCH.sub.2SCH.sub.3 Q.sub.3 SO.sub.2 CH.sub.3 Cl 3122 (CH.sub.2).sub.3 O OCH.sub.2Ph Q.sub.3 SO.sub.2 CH.sub.3 Cl 3123 (CH.sub.2).sub.3 O OPh Q.sub.3 SO.sub.2 CH.sub.3 Cl 3124 (CH.sub.2).sub.3 O OPh-2Cl Q.sub.3 SO.sub.2 CH.sub.3 Cl 3125 (CH.sub.2).sub.3 O OCH.sub.2CHCH.sub.2 Q.sub.3 SO.sub.2 CH.sub.3 Cl 3126 (CH.sub.2).sub.3 O OCH.sub.2CCH Q.sub.3 SO.sub.2 CH.sub.3 Cl 3127 (CH.sub.2).sub.3 O OCH.sub.2OC.sub.2 H.sub.5 Q.sub.3 SO.sub.2 CH.sub.3 Cl 3128 (CH.sub.2).sub.3 O H Q.sub.3 SO.sub.2 CH.sub.3 OCH.sub.3 3129 (CH.sub.2).sub.3 O OH Q.sub.3 SO.sub.2 CH.sub.3 OCH.sub.3 3130 (CH.sub.2).sub.3 O OCH.sub.3 Q.sub.3 SO.sub.2 CH.sub.3 OCH.sub.3 3131 (CH.sub.2).sub.3 O OC.sub.2 H.sub.5 Q.sub.3 SO.sub.2 CH.sub.3 OCH.sub.3 3133 (CH.sub.2).sub.3 O O-n-C.sub.3 H.sub.7 Q.sub.3 SO.sub.2 CH.sub.3 OCH.sub.3 3134 (CH.sub.2).sub.3 O O-i-C.sub.3 H.sub.7 Q.sub.3 SO.sub.2 CH.sub.3 O CH.sub.3 3135 (CH.sub.2).sub.3 O O-n-C.sub.4 H.sub.9 Q.sub.3 SO.sub.2 CH.sub.3 OCH.sub.3 3136 (CH.sub.2).sub.3 O O-i-C.sub.4 H.sub.9 Q.sub.3 SO.sub.2 CH.sub.3 OCH.sub.3 3137 (CH.sub.2).sub.3 O O-s-C.sub.4 H.sub.9 Q.sub.3 SO.sub.2 CH.sub.3 OCH.sub.3 3138 (CH.sub.2).sub.3 O O-t-C.sub.4 H.sub.9 Q.sub.3 SO.sub.2 CH.sub.3 OCH.sub.3 3139 (CH.sub.2).sub.3 O O(CH.sub.2).sub.2Cl Q.sub.3 SO.sub.2 CH.sub.3 OCH.sub.3 3140 (CH.sub.2).sub.3 O OCH.sub.2SCH.sub.3 Q.sub.3 SO.sub.2 CH.sub.3 OCH.sub.3 3141 (CH.sub.2).sub.3 O OCH.sub.2Ph Q.sub.3 SO.sub.2 CH.sub.3 OCH.sub.3 3142 (CH.sub.2).sub.3 O OPh Q.sub.3 SO.sub.2 CH.sub.3 OCH.sub.3 3143 (CH.sub.2).sub.3 O OPh-2Cl Q.sub.3 SO.sub.2 CH.sub.3 OCH.sub.3 3144 (CH.sub.2).sub.3 O O CH.sub.2CHCH.sub.2 Q.sub.3 SO.sub.2 CH.sub.3 OCH.sub.3 3145 (CH.sub.2).sub.3 O OCH.sub.2CCH Q.sub.3 SO.sub.2 CH.sub.3 OCH.sub.3 3146 (CH.sub.2).sub.3 O OCH.sub.2OC.sub.2 H.sub.5 Q.sub.3 SO.sub.2 CH.sub.3 OCH.sub.3 3147 (CH.sub.2).sub.3 O H Q.sub.3 OCH.sub.3 Cl 3148 (CH.sub.2).sub.3 O OH Q.sub.3 OCH.sub.3 Cl 3149 (CH.sub.2).sub.3 O OCH.sub.3 Q.sub.3 OCH.sub.3 Cl 3150 (CH.sub.2).sub.3 O OC.sub.2 H.sub.5 Q.sub.3 OCH.sub.3 Cl 3151 (CH.sub.2).sub.3 O O-n-C.sub.3 H.sub.7 Q.sub.3 OCH.sub.3 Cl 3152 (CH.sub.2).sub.3 O O-i-C.sub.3 H.sub.7 Q.sub.3 OCH.sub.3 Cl 3153 (CH.sub.2).sub.3 O O-n-C.sub.4 H.sub.9 Q.sub.3 OCH.sub.3 Cl 3154 (CH.sub.2).sub.3 O O-i-C.sub.4 H.sub.9 Q.sub.3 OCH.sub.3 Cl 3155 (CH.sub.2).sub.3 O O-s-C.sub.4 H.sub.9 Q.sub.3 OCH.sub.3 Cl 3156 (CH.sub.2).sub.3 O O-t-C.sub.4 H.sub.9 Q.sub.3 OCH.sub.3 Cl 3157 (CH.sub.2).sub.3 O O(CH.sub.2).sub.2Cl Q.sub.3 OCH.sub.3 Cl 3158 (CH.sub.2).sub.3 O OCH.sub.2S CH.sub.3 Q.sub.3 OCH.sub.3 Cl 3159 (CH.sub.2).sub.3 O OCH.sub.2Ph Q.sub.3 OCH.sub.3 Cl 3160 (CH.sub.2).sub.3 O OPh Q.sub.3 OCH.sub.3 Cl 3161 (CH.sub.2).sub.3 O OPh-2Cl Q.sub.3 OCH.sub.3 Cl 3162 (CH.sub.2).sub.3 O OCH.sub.2CHCH.sub.2 Q.sub.3 OCH.sub.3 Cl 3163 (CH.sub.2).sub.3 O OCH.sub.2CCH Q.sub.3 OCH.sub.3 Cl 3164 (CH.sub.2).sub.3 O OCH.sub.2OC.sub.2 H.sub.5 Q.sub. 3 C OH.sub.3 Cl 3165 (CH.sub.2).sub.3 O H Q.sub.3 OCH.sub.3 OCH.sub.3 3166 (CH.sub.2).sub.3 O OH Q.sub.3 OCH.sub.3 OCH.sub.3 3167 (CH.sub.2).sub.3 O OCH.sub.3 Q.sub.3 OCH.sub.3 OCH.sub.3 3168 (CH.sub.2).sub.3 O OC.sub.2 H.sub.5 Q.sub.3 OCH.sub.3 OCH.sub.3 3169 (CH.sub.2).sub.3 O O-n-C.sub.3 H.sub.7 Q.sub.3 OCH.sub.3 OCH.sub.3 3170 (CH.sub.2).sub.3 O O-i-C.sub.3 H.sub.7 Q.sub.3 OCH.sub.3 OCH.sub.3 3171 (CH.sub.2).sub.3 O O-n-C.sub.4 H.sub.9 Q.sub.3 OCH.sub.3 OCH.sub.3 3172 (CH.sub.2).sub.3 O O-i-C.sub.4 H.sub.9 Q.sub.3 OCH.sub.3 OCH.sub.3 3173 (CH.sub.2).sub.3 O O-s-C.sub.4 H.sub.9 Q.sub.3 OCH.sub.3 OCH.sub.3 3174 (CH.sub.2).sub.3 O O-t-C.sub.4 H.sub.9 Q.sub.3 OCH.sub.3 OCH.sub.3 3175 (CH.sub.2).sub.3 O O(CH.sub.2).s ub.2Cl Q.sub.3 OCH.sub.3 OCH.sub.3 3176 (CH.sub.2).sub.3 O OCH.sub.2SCH.s ub.3 Q.sub.3 OCH.sub.3 OCH.sub.3 3177 (CH.sub.2).sub.3 O OCH.sub.2Ph Q.sub.3 OCH.sub.3 OCH.sub.3 3178 (CH.sub.2).sub.3 O OPh Q.sub.3 OCH.sub.3 OCH.sub.3 3179 (CH.sub.2).sub.3 O OPh-2Cl Q.sub.3 OCH.sub.3 OCH.sub.3 3180 (CH.sub.2).sub.3 O OCH.sub.2CHCH.sub.2 Q.sub.3 OCH.sub.3 OCH.sub.3 3181 (CH.sub.2).sub.3 O OCH.sub.2CCH Q.sub.3 OCH.sub.3 OCH.sub.3 3182 (CH.sub.2).sub.3 O OCH.sub.2OC.sub.2 H.sub.5 Q.sub.3 OCH.sub.3 OCH.sub.3 3183 (CH.sub.2).sub.3 O H Q.sub.3 N(CH.sub.3).sub.2 Cl 3184 (CH.sub.2).su b.3 O OH Q.sub.3 N(CH.sub.3).sub.2 Cl 3185 (CH.sub.2).sub.3 O OCH.sub.3 Q.sub.3 N(CH.sub.3).sub.2 Cl 3186 (CH.sub.2).sub.3 O OC.sub.2 H.sub.5 Q.sub.3 N(CH.sub.3).sub.2 Cl 3187 (CH.sub.2).sub.3 O O-n-C.sub.3 H.sub.7 Q.sub.3 N(CH.sub.3).sub.2 Cl 3188 (CH.sub.2).sub.3 O O-i-C.sub.3 H.sub.7 Q.sub.3 N(CH.sub.3).sub.2 Cl 3189 (CH.sub.2).sub.3 O O-n-C.sub.4 H.sub.9 Q.sub.3 N(CH.sub.3).sub.2 Cl 3190 (CH.sub.2).sub.3 O O-i-C.sub.4 H.sub.9 Q.sub.3 N(CH.sub.3).sub.2 Cl 3191 (CH.sub.2).sub.3 O O-s-C.sub.4 H.sub.9 Q.sub.3 N(CH.sub.3).sub.2 Cl 3192 (CH.sub.2).sub.3 O O-t-C.sub.4 H.sub.9 Q.sub.3 N(CH.sub.3).sub.2 Cl 3193 (CH.sub.2).sub.3 O O(CH.sub.2).sub.2Cl Q.sub.3 N(CH.sub.3).sub.2 Cl 3194 (CH.sub.2).sub.3 O OCH.sub.2SCH.sub.3 Q.sub.3 N(CH.sub.3).sub.2 Cl 3195 (CH.sub.2).sub.3 O OCH.sub.2Ph Q.sub.3 N(CH.sub.3).sub.2 Cl 3196 (CH.sub.2).sub.3 O OPh Q.sub.3 N(CH.sub.3).sub. 2 Cl 3197 (CH.sub.2).sub.3 O OPh-2Cl Q.sub.3 N(CH.sub.3).sub.2 Cl 3198 (CH.sub.2).sub.3 O OCH.sub.2CHCH.sub.2 Q.sub.3 N(CH.sub.3).sub.2 Cl 3199 ( CH.sub.2).sub.3 O OCH.sub.2CCH Q.sub.3 N(CH.sub.3).sub.2 Cl 3200 (CH.sub.2).sub.3 O OCH.sub.2OC.sub.2 H.sub.5 Q.sub.3 N(CH.sub.3).sub.2 Cl 3201 (CH.sub.2).sub.3 O H Q.sub.3 N(CH.sub.3).sub.2 OCH.sub.3 3202 (CH.sub.2).sub.3 O OH Q.sub.3 N(CH.sub.3).sub.2 OCH.sub.3 3203 (CH.sub.2) .sub.3 O OCH.sub.3 Q.sub.3 N(CH.sub.3).sub.2 OCH.sub.3 3204 (CH.sub.2).su b.3 O OC.sub.2 H.sub.5 Q.sub.3 N(CH.sub.3 ).sub.2 OCH.sub.3 3205 (CH.sub.2).sub.3 O O-n-C.sub.3 H.sub.7 Q.sub.3 N(CH.sub.3).sub.2 OCH.sub.3 3206 (CH.sub.2).sub.3 O O-i-C.sub.3 H.sub.7 Q.sub.3 N(CH.sub.3).sub.2 OCH.sub.3 3207 (CH.sub.2).sub.3 O O-n-C.sub.4 H.sub.9 Q.sub.3 N(CH.sub.3).sub.2 OCH.sub.3 3208 (CH.sub.2).sub.3 O O-i-C.sub.4 H.sub.9 Q.sub.3 N(CH.sub.3).sub.2 OCH.sub.3 3209 (CH.sub.2).sub.3 O O-s-C.sub.4 H.sub.9 Q.sub.3 N(CH.sub.3).sub.2 OCH.sub.3 3210 (CH.sub.2).sub.3 O O-t-C.sub.4 H.sub.9 Q.sub.3 N(CH.sub.3).sub.2 OCH.sub.3 3211 (CH.sub.2).sub.3 O O(CH.sub.2).sub.2Cl Q.sub.3 N(CH.sub.3).sub.2 OCH.sub.3 3212 (CH.sub.2).s ub.3 O OCH.sub.2SCH.sub.3 Q.sub.3 N(CH.sub.3).sub.2 OCH.sub.3 3213 (CH.sub.2).sub.3 O OCH.sub.2Ph Q.sub.3 N(CH.sub.3).sub.2 OCH.sub.3 3214 (CH.sub.2).sub.3 O OPh Q.sub.3 N(CH.sub.3).sub.2 OCH.sub.3 3215 (CH.sub.2).sub.3 O OPh-2Cl Q.sub.3 N(CH.sub.3).sub.2 OCH.sub.3 3216 (CH.sub.2).sub.3 O OCH.sub.2CHCH.sub.2 Q.sub.3 N(CH.sub.3).sub.2 OCH.sub.3 3217 (CH.sub.2).sub.3 O OCH.sub.2CCH Q.sub.3 N(CH.sub.3).sub.2 OCH.sub.3 3218 (CH.sub.2).sub.3 O OCH.sub.2OC.sub.2 H.sub.5 Q.sub.3 N(CH.sub.3).sub.2 OCH.sub.3 3219 (CH.sub.2).sub.4 O H Q.sub.3 N(CH.sub.3) .sub.2 OCH.sub.3 3220 (CH.sub.2).sub.4 O OH Q.sub.3 N(CH.sub.3).sub.2 OCH.sub.3 3221 (CH.sub.2).sub.4 O OCH.sub.3 Q.sub.3 N(CH.sub.3).sub.2 OCH.sub.3 3222 (CH.sub.2).sub.4 O OC.sub.2 H.sub.5 Q.sub.3 N(CH.sub.3).sub.2 OCH.sub.3 3223 (CH.sub.2).sub.4 O O-n-C.sub.3 H.sub.7 Q.sub.3 N(CH.sub.3).sub.2 OCH.sub.3 3224 (CH.sub.2).sub.4 O O-i-C.sub.3 H.sub.7 Q.sub.3 N(CH.sub.3).sub.2 OCH.sub.3 3225 (CH.sub.2).sub.4 O O-n-C.sub.4 H.sub.9 Q.sub.3 N(CH.sub.3).sub.2 OCH.sub.3 3226 (CH.sub.2).sub.4 O O-i-C.sub.4 H.sub.9 Q.sub.3 N(CH.sub.3).sub.2 OCH.sub.3 3227 (CH.sub.2).sub.4 O O-s-C.sub.4 H.sub.9 Q.sub.3 N(CH.sub.3).sub.2 OCH.sub.3 3228 (CH.sub.2).sub.4 O O-t-C.sub.4 H.sub.9 Q.sub.3 N(CH.sub.3).sub.2 OCH.sub.3 3229 (CH.sub.2).sub.4 O O(CH.sub.2).sub.2Cl Q.sub.3 N(CH.sub.3).sub.2 OCH.sub.3 3230 (CH.sub.2).s ub.4 O OCH.sub.2SCH.sub.3 Q.sub.3 N(CH.sub.3).sub.2 OCH.sub.3 3231 (CH.sub.2).sub.4 O OCH.sub.2Ph Q.sub.3 N(CH.sub.3).sub.2 OCH.sub.3 3232 (CH.sub.2).sub.4 O OPh Q.sub.3 N(CH.sub.3 ).sub.2 OCH.sub.3 3233 (CH.sub.2).sub.4 O OPh-2Cl Q.sub.3 N(CH.sub.3).sub.2 OCH.sub.3 3234 (CH.sub.2).sub.4 O OCH.sub.2CHCH.sub.2 Q.sub.3 N(CH.sub.3).sub.2 OCH.sub.3 3235 (CH.sub.2).sub.4 O OCH.sub.2CCH Q.sub.3 N(CH.sub.3).sub.2 OCH.sub.3 3236 (CH.sub.2).sub.4 O OCH.sub.2OC.sub.2 H.sub.5 Q.sub.3 N(CH.sub.3).sub.2 OCH.sub.3 3237 (CH.sub.2).sub.4 O H Q.sub.3 Cl OCH.sub.3 3238 (CH.sub.2).sub.4 O OH Q.sub.3 Cl OCH.sub.3 3239 (CH.sub.2) .sub.4 O OCH.sub.3 Q.sub.3 Cl OCH.sub.3 3240 (CH.sub.2).sub.4 O OC.sub.2 H.sub.5 Q.sub.3 Cl OCH.sub.3 3241 (CH.sub.2).sub.4 O O-n-C.sub.3 H.sub.7 Q.sub.3 Cl OCH.sub.3 3242 (CH.sub.2).sub.4 O O-i-C.sub.3 H.sub.7 Q.sub. 3 Cl OCH.sub.3 3243 (CH.sub.2).sub.4 O O-n-C.sub.4 H.sub.9 Q.sub.3 Cl OCH.sub.3 3244 (CH.sub.2).sub.4 O O-i-C.sub.4 H.sub.9 Q.sub.3 Cl OCH.sub.3 3245 (CH.sub.2).sub.4 O O-s-C.sub.4 H.sub.9 Q.sub.3 Cl OCH.sub.3 3246 (CH.sub.2).sub.4 O O-t-C.sub.4 H.sub.9 Q.sub.3 Cl OCH.sub.3 3247 (CH.sub.2).sub.4 O O(CH.sub.2).sub.2Cl Q.sub.3 Cl OCH.sub.3 3248 (CH.sub.2).sub.4 O OCH.sub.2SCH.sub.3 Q.sub.3 Cl OCH.sub.3 3249 (CH.sub.2).sub.4 O OCH.sub.2Ph Q.sub.3 Cl OCH.sub.3 3250 (CH.sub.2) .sub.4 O OPh Q.sub.3 Cl OCH.sub.3 3251 (CH.sub.2).sub.4 O OPh-2Cl Q.sub.3 Cl OCH.sub.3 3252 (CH.sub.2).sub.4 O OCH.sub.2CHCH.sub.2 Q.sub.3 Cl OCH.sub.3 3253 (CH.sub.2).sub.4 O OCH.sub.2C CH Q.sub.2 Cl OCH.sub.3 3254 (CH.sub.2).sub.4 O OCH.sub.2OC.sub.2 H.sub.5 Q.sub.2 Cl OCH.sub.3 3255 (CH.sub.2).sub.4 O H Q.sub.2 OCH.sub.3 OC.sub.2 H.sub.5 3256 (CH.sub.2).sub.4 O OH Q.sub.2 OCH.sub.3 OC.sub.2 H.sub.5 3257 (CH.sub.2).sub.4 O OCH.sub.3 Q.sub.2 OCH.sub.3 OC.sub.2 H.sub.5 3258 (CH.sub.2).sub.4 O OC.sub.2 H.sub.5 Q.sub.2 OCH.sub.3 OC.sub.2 H.sub.5 3259 (CH.sub.2).sub.4 O O-n-C.sub.3 H.sub.7 Q.sub.2 OCH.sub.3 OC.sub.2 H.sub.5 3260 (CH.sub.2).sub.4 O O-i-C.sub.3 H.sub.7 Q.sub.2 OCH.sub.3 OC.sub.2 H.sub.5 3261 (CH.sub.2).sub.4 O O-n-C.sub.4 H.sub.9 Q.sub.2 OCH.sub.3 OC.sub.2 H.sub.5 3262 (CH.sub.2).sub.4 O O-i-C.sub.4 H.sub.9 Q.sub.2 O CH.sub.3 OC.sub.2 H.sub.5 3263 (CH.sub.2).sub.4 O O-s-C.sub.4 H.sub.9 Q.sub.2 OCH.sub.3 OC.sub.2 H.sub.5 3264 (CH.sub.2).sub.4 O O-t-C.sub.4 H.sub.9 Q.sub.2 OCH.sub.3 OC.sub.2 H.sub.5 3265 (CH.sub.2).sub.4 O O(CH.sub.2).sub.2Cl Q.sub.2 OCH.sub.3 OC.sub.2 H.sub.5 3266 (CH.sub.2).sub.4 O OCH.sub.2SCH.sub.3 Q.sub.2 OCH.sub.3 OC.sub.2 H.sub.5 3267 (CH.sub.2).sub.4 O OCH.sub.2Ph Q.sub.2 OCH.sub.3 OC.sub.2 H.sub.5 3268 (CH.sub.2).sub.4 O OPh Q.sub.2 OCH.sub.3 OC.sub.2 H.sub.5 3269 (CH.sub.2).sub.4 O OPh-2Cl Q.sub.2 OCH.sub.3 OC.sub.2 H.sub.5 3270 (CH.sub.2).sub.4 O OCH.sub.2CHCH.sub.2 Q.sub.2 OCH.sub.3 OC.sub.2 H.sub.5 3271 (CH.sub.2).sub.4 O OCH.sub.2C CH Q.sub.2 OCH.sub.3 OC.sub.2 H.sub.5 3272 (CH.sub.2).sub.4 O OCH.sub.2OC.sub.2 H.sub.5 Q.sub.2 OCH.sub.3 OC.sub.2 H.sub.5 3273 (CH.sub.2).sub.4 O H Q.sub.2 OC.sub.2 H.sub.5 OC.sub.2 H.sub.5 3274 (CH.sub.2).sub.4 O OH Q.sub.2 OC.sub.2 H.sub.5 OC.sub.2 H.sub.5 3275 (CH.sub.2).sub.4 O OCH.sub.3 Q.sub.2 OC.sub.2 H.sub.5 OC.sub.2 H.sub.5 3276 (CH.sub.2).sub.4 O OC.sub.2 H.sub.5 Q.sub.2 OC.sub.2 H.sub.5 OC.sub.2 H.sub.5 3277 (CH.sub.2).sub.4 O O-n-C.sub.3 H.sub.7 Q.sub.2 OC.sub.2 H.sub.5 OC.sub.2 H.sub.5 3278 (CH.sub.2).sub.4 O O-i-C.sub.3 H.sub.7 Q.sub.2 OC.sub.2 H.sub.5 OC.sub.2 H.sub.5 3279 (CH.sub.2).sub.4 O O-n-C.sub.4 H.sub.9 Q.sub.2 OC.sub.2 H.sub.5 OC.sub.2 H.sub.5 3280 (CH.sub.2).sub.4 O O-i-C.sub.4 H.sub.9 Q.sub.2 OC.sub.2 H.sub.5 OC.sub.2 H.sub.5 3281 (CH.sub.2).sub.4 O O-s-C.sub.4 H.sub.9 Q.sub.2 OC.sub.2 H.sub.5 OC.sub.2 H.sub.5 3282 (CH.sub.2).sub.4 O O-t-C.sub.4 H.sub.9 Q.sub.2 OC.sub.2 H.sub.5 OC.sub.2 H.sub.5 3283 (CH.sub.2).sub.4 O O(CH.sub.2).sub.2Cl Q.sub.2 OC.sub.2 H.sub.5 OC.sub.2 H.sub.5 3284 (CH.sub.2).sub.4 O OCH.sub.2SCH.sub.3 Q.sub.2 OC.sub.2 H.sub.5 OC.sub.2 H.sub.5 3285 (CH.sub.2).sub.4 O OCH.sub.2Ph Q.sub.2 OC.sub.2 H.sub.5 OC.sub.2 H.sub.5 3286 (CH.sub.2).sub.4 O OPh Q.sub.2 OC.sub.2 H.sub.5 OC.sub.2 H.sub.5 3287 (CH.sub.2).sub.4 O OPh-2Cl Q.sub.2 OC.sub.2 H.sub.5 OC.sub.2 H.sub.5 3288 (CH.sub. 2).sub.4 O OCH.sub.2CHCH.sub.2 Q.sub.2 OC.sub.2 H.sub.5 OC.sub.2 H.sub.5 3289 (CH.sub.2).sub.4 O OCH.sub.2CCH Q.sub.2 OC.sub.2 H.sub.5 OC.sub.2 H.sub.5 3290 (CH.sub.2).sub.4 O OCH.sub.2OC.sub.2 H.sub.5 Q.sub.2 OC.sub.2 H.sub.5 OC.sub.2 H.sub.5 3291 (CH.sub.2).sub.4 O H Q.sub.3 SCH.sub.3 Cl 3292a (CH.sub.2).sub.4 O OH Q.sub.3 SCH.sub.3 Cl cis 3292b (CH.sub.2).sub.4 O OH Q.sub.3 SCH.sub.3 Cl trans 3293a (CH.sub.2).sub.4 O OCH.sub.3 Q.sub.3 SCH.sub.3 Cl cis 3293b (CH.sub.2).sub.4 O OCH.sub.3 Q.sub.3 SCH.sub.3 Cl trans 3294a (CH.sub.2).sub.4 O OC.sub.2 H.sub.5 Q.sub.3 SCH.sub.3 Cl cis 3294b (CH.sub.2).sub.4 O OC.sub.2 H.sub. 5 Q.sub.3 SCH.sub.3 Cl trans 3295 (CH.sub.2).sub.4 O O-n-C.sub.3 H.sub.7 Q.sub.3 SCH.sub.3 Cl 3296 (CH.sub.2).sub.4 O O-i-C.sub.3 H.sub.7 Q.sub.3 SCH.sub.3 Cl 3297 (CH.sub.2).sub.4 O O-n-C.sub.4 H.sub.9 Q.sub.3 SCH.sub.3 Cl 3298 (CH.sub.2).sub.4 O O-i-C.sub.4 H.sub.9 Q.sub.3 SCH.sub.3 Cl 3299 (CH.sub.2).sub.4 O O-s-C.sub.4 H.sub.9 Q.sub.3 SCH.sub.3 Cl 3300 (CH.sub.2).sub.4 O O-t-C.sub.4 H.sub.9 Q.sub.3 SCH.sub.3 Cl 3301 (CH.sub.2).sub.4 O O(CH.sub.2).sub.2Cl Q.sub.3 SCH.sub.3 Cl 3302 (CH.sub.2).sub.4 O OCH.sub.2SCH.sub.3 Q.sub.3 SCH.sub.3 Cl 3303 (CH.sub.2).sub.4 O OCH.sub.2Ph Q.sub.3 SCH.sub.3 Cl 3304 (CH.sub.2).sub.4 O OPh Q.sub.3 SCH.sub.3 Cl 3305 (CH.sub.2).sub.4 O OPh-2Cl Q.sub.3 SCH.sub.3 Cl 3306 (CH.sub.2).sub.4 O OCH.sub.2CHCH.sub.2 Q.sub.3 SCH.sub.3 Cl 3307 (CH.sub.2).sub.4 O OCH.sub.2CCH Q.sub.3 SCH.sub.3 Cl 3308 (CH.sub.2).sub.4 O OCH.sub.2OC.sub.2 H.sub.5 Q.sub.3 SCH.sub.3 Cl 3309 (CH.sub.2).sub.4 O H Q.sub.3 SCH.sub.3 OCH.sub.3 3310a ( CH.sub.2).sub.4 O OH Q.sub.3 SCH.sub.3 OCH.sub.3 cis 3310b (CH.sub.2).sub .4 O OH Q.sub.3 SCH.sub.3 OCH.sub.3 trans 3311 (CH.sub.2).sub.4 O OCH.sub.3 Q.sub.3 SCH.sub.3 OCH.sub.3 3312a (CH.sub.2).sub.4 O OC.sub.2 H.sub.5 Q.sub.3 SCH.sub.3 OCH.sub.3 cis 3312b (CH.sub.2).sub.4 O OC.sub.2 H.sub.5 Q.sub.3 SCH.sub.3 OCH.sub.3 trans 3313 (CH.sub.2).sub.4 O O-n-C.sub.3 H.sub.7 Q.sub.3 SCH.sub.3 OCH.sub.3 3314 (CH.sub.2).sub.4 O O-i-C.sub.3 H.sub.7 Q.sub.3 SCH.sub.3 OCH.sub.3 3315 (CH.sub.2).sub.4 O O-n-C.sub.4 H.sub.9 Q.sub.3 SCH.sub.3 OCH.sub.3 3316 (CH.sub.2).sub.4 O O-i-C.sub.4 H.sub.9 Q.sub.3 SCH.sub.3 OCH.sub.3 3317 (CH.sub.2).sub.4 O O-s-C.sub.4 H.sub.9 Q.sub.3 SCH.sub.3 OCH.sub.3 3318 (CH.sub.2).sub.4 O O-t-C.sub.4 H.sub.9 Q.sub.3 SCH.sub.3 OCH.sub.3 3319 (CH.sub.2).sub.4 O O(CH.sub.2).sub.2Cl Q.sub.3 SCH.sub.3 OCH.sub.3 3320 (CH.sub.2).sub.4 O OCH.sub.2SCH.sub.3 Q.sub.3 SCH.sub.3 OCH.sub.3 3321 (CH.sub.2).sub.4 O OCH.sub.2Ph Q.sub.3 SCH.sub.3 OCH.sub.3 3322 (CH.sub.2).sub.4 O OPh Q.sub.3 SCH.sub.3 OCH.sub.3 3323 (CH.sub.2).sub.4 O OPh-2Cl Q.sub.3 SCH.sub.3 OCH.sub.3 3324 (CH.sub.2).sub.4 O OCH.sub.2CHCH.sub.2 Q.sub.3 C SH.sub.3 OCH.sub.3 3325 (CH.sub.2).sub.4 O OCH.sub.2CCH Q.sub.3 SCH.sub.3 OCH.sub.3 3326 (CH.sub.2).sub.4 O OCH.sub.2OC.sub.2 H.sub.5 Q.sub.3 SCH.sub.3 OCH.sub.3 3327 (CH.sub.2).sub.4 O H Q.sub.3 SO.sub.2 CH.sub.3 Cl 3328 (CH.sub.2).sub.4 O OH Q.sub.3 SO.sub.2 CH.sub.3 Cl 3329 (CH.sub.2).sub.4 O OCH.sub.3 Q.sub.3 SO.sub.2 CH.sub.3 Cl 3330a (CH.sub.2).sub.4 O OC.sub.2 H.sub.5 Q.sub.3 SO.sub.2 CH.sub.3 Cl cis 3330b (CH.sub.2).sub.4 O OC.sub.2 H.sub.5 Q.sub.3 SO.sub.2 CH.sub.3 Cl trans 3331 (CH.sub.2).sub.4 O O-n-C.sub.3 H.sub.7 Q.sub.3 SO.sub.2 CH.sub.3 Cl 3332 (CH.sub.2).sub.4 O O-i-C.sub.3 H.sub.7 Q.sub.3 SO.sub.2 CH.sub.3 Cl 3333 (CH.sub.2).sub.4 O O-n-C.sub.4 H.sub.9 Q.sub.3 SO.sub.2 CH.sub.3 Cl 3334 (CH.sub.2).sub.4 O O-i-C.sub.4 H.sub.9 Q.sub.3 SO.sub.2 CH.sub.3 Cl 3335 (CH.sub.2).sub.4 O O-s-C.sub.4 H.sub.9 Q.sub.3 SO.sub.2 CH.sub.3 Cl 3336 (CH.sub.2).sub.4 O O-t-C.sub.4 H.sub.9 Q.sub.3 SO.sub.2 CH.sub.3 Cl 3337 (CH.sub.2).sub.4 O O(CH.sub.2).sub.2Cl Q.sub.3 SO.sub.2 CH.sub.3 Cl 3338 (CH.sub.2).sub.4 O OCH.sub.2SCH.sub.3 Q.sub.3 SO.sub.2 CH.sub.3 Cl 3339 (CH.sub.2).sub.4 O OCH.sub.2Ph Q.sub.3 SO.sub.2 CH.sub.3 Cl 3340 (CH.sub.2).sub.4 O OPh Q.sub.3 SO.sub.2 CH.sub.3 Cl 3341 (CH.sub.2).sub.4 O OPh-2Cl Q.sub.3 SO.sub.2 CH.sub.3 Cl 3342 (CH.sub.2).sub.4 O OCH.sub.2 CHCH.sub.2 Q.sub.3 SO.sub.2 CH.sub.3 Cl 3343 (CH.sub.2).sub.4 O OCH.sub.2CCH Q.sub.3 SO.sub.2 CH.sub.3 Cl 3344 (CH.sub.2).sub.4 O OCH.sub.2OC.sub.2 H.sub.5 Q.sub.3 SO.sub.2 CH.sub.3 Cl 3345 (CH.sub.2).sub.4 O H Q.sub.3 SO.sub.2 CH.sub.3 OCH.sub.3 3346 (CH.sub.2).sub.4 O OH Q.sub.3 SO.sub.2 CH.sub.3 OCH.sub.3 3347 (CH.sub.2).sub.4 O OCH.sub.3 Q.sub.3 SO.sub.2 CH.sub.3 OCH.sub.3 3348 (CH.sub.2).sub.4 O OC.sub.2 H.sub.5 Q.sub.3 SO.sub.2 CH.sub.3 OCH.sub.3 3349 (CH.sub.2).sub.4 O O-n-C.sub.3 H.sub.7 Q.sub.3 SO.sub.2 CH.sub.3 OCH.sub.3 3350 (CH.sub.2).sub.4 O O-i-C.sub.3 H.sub.7 Q.sub.3 SO.sub.2 CH.sub.3 OCH.sub.3 3351 (CH.sub.2).sub.4 O O-n-C.sub.4 H.sub.9 Q.sub.3 SO.sub.2 CH.sub.3 OCH.sub.3 3352 (CH.sub.2).sub.4 O O-i-C.sub.4 H.sub.9 Q.sub.3 SO.sub.2 CH.sub.3 OCH.sub.3 3353 (CH.sub.2).sub.4 O O-s-C.sub.4 H.sub.9 Q.sub.3 SO.sub.2 CH.sub.3 OCH.sub.3 3354 (CH.sub.2).sub.4 O O-t-C.sub.4 H.sub.9 Q.sub.3 SO.sub.2 CH.sub.3 OCH.sub.3 3355 (CH.sub.2).sub.4 O O(CH.sub.2).sub.2Cl Q.sub.3 SO.sub.2 CH.sub.3 OCH.sub.3 3356 (CH.sub.2).sub.4 O OCH.sub.2SCH.sub.3 Q.sub.3 SO.sub.2 CH.sub.3 OCH.sub.3 3357 (CH.sub.2).sub.4 O OCH.sub.2Ph Q.sub.3 SO.sub.2 CH.sub.3 OCH.sub.3 3358 (CH.sub.2).sub.4 O OPh Q.sub.3 SO.sub.2 CH.sub.3 OCH.sub.3 3359 (CH.sub.2).sub.4 O OPh-2Cl Q.sub.3 SO.sub.2 CH.sub.3 OCH.sub.3 3360 (CH.sub.2).sub.4 O OCH.sub.2CHCH.sub.2 Q.sub.3 SO.sub.2 CH.sub.3 OCH.sub.3 3361 (CH.sub.2).sub.4 O OCH.sub.2CCH Q.sub.3 SO.sub.2 CH.sub.3 OCH.sub.3 3362 (CH.sub.2).sub.4 O OCH.sub.2OC.sub.2 H.sub.5 Q.sub.3 SO.sub.2 CH.sub.3 OCH.sub.3 3363 (CH.sub.2).sub.4 O H Q.sub.3 OCH.sub.3 Cl 3364 (CH.sub.2).sub.4 O OH Q.sub.3 OCH.sub.3 Cl 3365 (CH.sub.2).sub.4 O OCH.sub.3 Q.sub.3 OCH.sub.3 Cl 3366a (CH.sub.2).s ub.4 O OC.sub.2 H.sub.5 Q.sub.3 OCH.sub.3 Cl cis 3366b (CH.sub.2).sub.4 O OC.sub.2 H.sub.5 Q.sub.3 OCH.sub.3 Cl trans 3367 (CH.sub.2).sub.4 O O-n-C.sub.3 H.sub.7 Q.sub.3 OCH.sub.3 Cl 3368 (CH.sub.2).sub.4 O O-i-C.sub.3 H.sub.7 Q.sub.3 OCH.sub.3 Cl 3369 (CH.sub.2).sub.4 O O-n-C.sub.4 H.sub.9 Q.sub.3 OCH.sub.3 Cl 3370 (CH.sub.2).sub.4 O O-i-C.sub. 4 H.sub.9 Q.sub.3 OCH.sub.3 Cl 3371 (CH.sub.2).sub.4 O O-s-C.sub.4 H.sub.9 Q.sub.3 OCH.sub.3 Cl 3372 (CH.sub.2).sub.4 O O-t-C.sub.4 H.sub.9 Q.sub.3 OCH.sub.3 Cl 3373 (CH.sub.2).sub.4 O O(CH.sub.2).sub.2Cl Q.sub.3 OCH.sub.3 Cl 3374 (CH.sub.2).sub.4 O OCH.sub.2SCH.sub.3 Q.sub.3 OCH.sub.3 Cl 3375 (CH.sub.2).sub.4 O OCH.sub.2P h Q.sub.3 OCH.sub.3 Cl 3376 (CH.sub.2).sub.4 O OPh Q.sub.3 OCH.sub.3 Cl 3377 (CH.sub.2).sub.4 O OPh-2Cl Q.sub.3 OCH.sub.3 Cl 3378 (CH.sub.2).sub. 4 O OCH.sub.2CHCH.sub.2 Q.sub.3 OCH.sub.3 Cl 3379a (CH.sub.2).sub.4 O OCH.sub.2CCH Q.sub.3 OCH.sub.3 Cl cis 3379b (CH.sub.2).sub.4 O OCH.sub.2CC H Q.sub.3 OCH.sub.3 Cl trans 3380 (CH.sub.2).sub.4 O OCH.sub.2OC.sub.2 H.sub.5 Q.sub.3 OCH.sub.3 Cl 3381 (CH.sub.2).sub.4 O H Q.sub.3 OCH.sub.3 OCH.sub.3 3382 (CH.sub.2).sub.4 O OH Q.sub.3 OCH.sub.3 OCH.sub.3 3383 (CH.sub.2).sub.4 O OCH.sub.3 Q.sub.3 OCH.sub.3 OCH.sub.3 3384 (CH.sub.2). sub.4 O OC.sub.2 H.sub.5 Q.sub.3 OCH.sub.3 OCH.sub.3 3385 (CH.sub.2).sub.4 O O-n-C.sub.3 H.sub.7 Q.sub.3 OCH.sub.3 OCH.sub.3 3386 (CH.sub.2).sub.4 O O-i-C.sub.3 H.sub.7 Q.sub.3 OCH.sub.3 OCH.sub.3 3387 (CH.sub.2).sub.4 O O-n-C.sub.4 H.sub.9 Q.sub.3 OCH.sub.3 OCH.sub.3 3388 (CH.sub.2).sub.4 O O-i-C.sub.4 H.sub.9 Q.sub.3 OCH.sub.3 OCH.sub.3 3389 (CH.sub.2).sub.4 O O-s-C.sub.4 H.sub. 9 Q.sub.3 OCH.sub.3 OCH.sub.3 3390 (CH.sub.2).sub.4 O O-t-C.sub.4 H.sub.9 Q.sub.3 OCH.sub.3 OCH.sub.3 3391 (CH.sub.2).sub.4 O O(CH.sub.2).s ub.2Cl Q.sub.3 OCH.sub.3 OCH.sub.3 3392 (CH.sub.2).sub.4 O OCH.sub.2SCH.s ub.3 Q.sub.3 OCH.sub.3 OCH.sub.3 3393 (CH.sub.2).sub.4 O OCH.sub.2Ph Q.sub.3 OCH.sub.3 OCH.sub.3 3394 (CH.sub.2).sub.4 O OPh Q.sub.3 OCH.sub.3 OCH.sub.3 3395 (CH.sub.2).sub.4 O OPh-2Cl Q.sub.3 OCH.sub.3 OCH.sub.3 3396 (CH.sub.2).sub.4 O OCH.sub.2CHCH.sub.2 Q.sub.3 OCH.sub.3 OCH.sub.3 3397 (CH.sub.2).sub.4 O OCH.sub.2CCH Q.sub.3 OCH.sub.3 OCH.sub.3 3398 (CH.sub.2).sub.4 O OCH.sub.2OC.sub.2 H.sub.5 Q.sub.3 O CH.sub.3 OCH.sub.3 3399 (CH.sub.2).sub.4 O H Q.sub.3 N(CH.sub.3).sub.2 Cl 3400 (CH.sub.2).sub.4 O OH Q.sub.3 N(CH.sub.3).sub.2 Cl 3401 (CH.sub.2).sub.4 O OCH.sub.3 Q.sub.3 N(CH.sub.3).sub.2 Cl 3402 (CH.sub.2).sub.4 O OC.sub.2 H.sub.5 Q.sub.3 N(CH.sub.3).sub.2 Cl 3403 (CH.sub.2).sub.4 O O-n-C.sub.3 H.sub.7 Q.sub.3 N(CH.sub.3).sub.2 Cl 3404 ( CH.sub.2).sub.4 O O-i-C.sub.3 H.sub.7 Q.sub.3 N(CH.sub.3).sub.2 Cl 3405 (CH.sub.2).sub.4 O O-n-C.sub.4 H.sub.9 Q.sub.3 N(CH.sub.3).sub.2 Cl 3406 ( CH.sub.2).sub.4 O O-i-C.sub.4 H.sub.9 Q.sub.3 N(CH.sub.3).sub.2 Cl 3407 (CH.sub.2).sub.4 O O-s-C.sub.4 H.sub.9 Q.sub.3 N(CH.sub.3).sub.2 Cl 3408 ( CH.sub.2).sub.4 O O-t-C.sub.4 H.sub.9 Q.sub.3 N(CH.sub.3).sub.2 Cl 3409 (CH.sub.2).sub.4 O O(CH.sub.2 ).sub.2Cl Q.sub.3 N(CH.sub.3).sub.2 Cl 3410 (CH.sub.2).sub.4 O OCH.sub.2SCH.sub.3 Q.sub.3 OCH.sub.3 OCH.sub.3 3411 (CH.sub.2).sub.4 O OCH.sub.2Ph Q.sub.3 N(CH.sub.3).sub.2 Cl 3412 (CH.sub.2).sub.4 O OPh Q.sub.3 N(CH.sub.3).sub.2 Cl 3413 (CH.sub.2).sub.4 O OPh-2Cl Q.sub.3 N(CH.sub.3).sub.2 Cl 3414 (CH.sub.2).sub.4 O OCH.sub.2C HCH.sub.2 Q.sub.3 N(CH.sub.3).sub.2 Cl 3415 (CH.sub.2).sub.4 O OCH.sub.2CC H Q.sub.3 N(CH.sub.3).sub.2 Cl 3416 (CH.sub.2).sub.4 O OCH.sub.2OC.sub.2 H.sub.5 Q.sub.3 N(CH.sub.3).sub.2 Cl 3417 (CH.sub.2).sub.4 O H Q.sub.3 N(CH.sub.3).sub.2 OCH.sub.3 3418 (CH.sub.2).sub.4 O OH Q.sub.3 N(CH.sub.3 ).sub.2 OCH.sub.3 3419 (CH.sub.2).sub.4 O OCH.sub.3 Q.sub.3 N(CH.sub.3). sub.2 OCH.sub.3 3420 (CH.sub.2).sub.4 O OC.sub.2 H.sub.5 Q.sub.3 N(CH.sub.3).sub.2 OCH.sub.3 3421 (CH.sub.2).sub.4 O O-n-C.sub.3 H.sub.7 Q.sub.3 N(CH.sub.3).sub.2 OCH.sub.3 3422 (CH.sub.2).sub.4 O O-i-C.sub.3 H.sub.7 Q.sub.3 N(CH.sub.3).sub.2 OCH.sub.3 3422 (CH.sub.2).sub.4 O O-n-C.sub.4 H.sub.9 Q.sub.3 N(CH.sub.3).sub.2 OCH.sub.3 3424 (CH.sub.2).sub.4 O O-i-C.sub.4 H.sub.9 Q.sub.3 N(CH.sub.3).sub.2 OCH.sub.3 3425 (CH.sub.2).sub.4 O O-s-C.sub.4 H.sub.9 Q.sub.3 N(CH.sub.3).sub.2 OCH.sub.3 3426 (CH.sub.2).sub.4 O O-t-C.sub.4 H.sub.9 Q.sub.3 N(CH.sub.3).sub.2 OCH.sub.3 3427 (CH.sub.2).sub.4 O O(CH.sub.2).sub.2Cl Q.sub.3 N(CH.sub.3).sub.2 OCH.sub.3 3428 (CH.sub.2).s ub.4 O OCH.sub.2SCH.sub.3 Q.sub. 3 N(CH.sub.3).sub.2 OCH.sub.3 3429 (CH.sub.2).sub.4 O OCH.sub.2Ph Q.sub.3 N(CH.sub.3).sub.2 OCH.sub.3 3430 (CH.sub.2).sub.4 O OPh Q.sub.3 N(CH.sub.3).sub.2 OCH.sub.3 3431 (CH.sub.2 ).sub.4 O OPh-2Cl Q.sub.3 N(CH.sub.3).sub.2 OCH.sub.3 3432 (CH.sub.2).sub .4 O OCH.sub.2CHCH.sub.2 Q.sub.3 N(CH.sub.3).sub.2 OCH.sub.3 3433 (CH.sub.2).sub.4 O OCH.sub.2CCH Q.sub.3 N(CH.sub.3).sub.2 OCH.sub.3 3434 ( CH.sub.2).sub.4 O OCH.sub.2OC.sub.2 H.sub.5 Q.sub.3 N(CH.sub.3).sub.2 OCH.sub.3 ##STR25##
TABLE 5__________________________________________________________________________Compound No. R.sup.3 R.sup.4 X Y Remarks__________________________________________________________________________5001 H CH.sub.3 F OH rac5002 H CH.sub.3 F OCH.sub.35003 H CH.sub.3 F OC.sub.2 H.sub.5 rac5004 H CH.sub.3 F O(CH.sub.2).sub.2Cl5005 H CH.sub.3 F OCH.sub.2SCH.sub.35006 H CH.sub.3 F OCH.sub.2 -Ph5007 H CH.sub.3 F O-Ph5008 H CH.sub.3 F OCH.sub.2CHCH.sub.25009 H CH.sub.3 F OCH.sub.2CCH5010 H CH.sub.3 F OCH.sub.2OC.sub.2 H.sub.55011 H CH.sub.3 F NH.sub.25012 H CH.sub.3 F NHCH.sub. 35013 H CH.sub.3 F N(CH.sub.3)-Ph5014 H CH.sub.3 F NHOH5015 H CH.sub.3 F N(CH.sub.3)OH5016 H CH.sub.3 F NHOCH.sub.35017 H CH.sub.3 F NHOCH.sub.2CHCH.sub.25018 H CH.sub.3 F NHOCH.sub.2CCH5019 H CH.sub.3 F NHOCH.sub.2 -Ph5020 H CH.sub.3 F NHOCH.sub.2CO.sub.2CH.sub.35021 H CH.sub.3 F NHN(CH.sub.3).sub.25022 H CH.sub.3 F NH-2-pyridyl5023 H CH.sub.3 F N(CH.sub.3).sub.25024 H CH.sub.3 F N.sub.35025 H CH.sub.3 F SCH.sub.35026 H CH.sub.3 F S-i-C.sub.3 H.sub.75027 H C.sub.2 H.sub.5 F OH5028 H C.sub.2 H.sub.5 F OCH.sub.35029 H C.sub.2 H.sub.5 F OC.sub.2 H.sub.55030 H C.sub.2 H.sub.5 F O(CH.sub.2).sub.2Cl5031 H C.sub.2 H.sub.5 F OCH.sub.2SCH.sub.35032 H C.sub.2 H.sub.5 F OCH.sub.2 -Ph5033 H C.sub.2 H.sub.5 F O-Ph5034 H C.sub.2 H.sub.5 F OCH.sub.2CHCH.sub.25035 H C.sub.2 H.sub.5 F OCH.sub.2CCH5036 H C.sub.2 H.sub.5 F NH.sub.25037 H C.sub.2 H.sub.5 F NHCH.sub.35038 H C.sub.2 H.sub.5 F N(CH.sub.3)-Ph5039 H C.sub.2 H.sub.5 F NHOH5040 H C.sub.2 H.sub.5 F N(CH.sub.3)OH5041 H C.sub.2 H.sub.5 F NHOCH.sub.35042 H C.sub.2 H.sub.5 F NHOCH.sub.2CHCH.sub.25043 H C.sub.2 H.sub.5 F NHOCH.sub.2CCH5044 H C.sub.2 H.sub.5 F NHOCH.sub.2 -Ph5045 H C.sub.2 H.sub.5 F NHOCH.sub.2CO.sub.2CH.sub.35046 H C.sub.2 H.sub.5 F NHN(CH.sub.3).sub.25047 H C.sub.2 H.sub.5 F NH-2-pyridyl5048 H C.sub.2 H.sub.5 F N(CH.sub.3).sub. 25049 H C.sub.2 H.sub.5 F N.sub.35050 H C.sub.2 H.sub.5 F SCH.sub.35051 H C.sub.2 H.sub.5 F S-i-C.sub.3 H.sub.75052 H C.sub.3 H.sub.7 F OH5053 H C.sub.3 H.sub.7 F OCH.sub.35054 H C.sub.3 H.sub.7 F OC.sub.2 H.sub.55055 H C.sub.3 H.sub.7 F O(CH.sub.2).sub.2Cl5056 H C.sub.3 H.sub.7 F OCH.sub.2SCH.sub.35057 H C.sub.3 H.sub.7 F OCH.sub.2 -Ph5058 H C.sub.3 H.sub.7 F O-Ph5059 H C.sub.3 H.sub.7 F OCH.sub.2CHCH.sub.25060 H C.sub.3 H.sub.7 F OCH.sub.2CCH5061 H C.sub.3 H.sub.7 F OCH.sub.2OC.sub.2 H.sub.55062 H C.sub.3 H.sub.7 F NH.sub.25063 H C.sub.3 H.sub.7 F NHCH.sub.35064 H C.sub.3 H.sub.7 F N(CH.sub.3)-Ph5065 H C.sub.3 H.sub.7 F NHOH5066 H C.sub.3 H.sub.7 F N(CH.sub.3)OH5067 H C.sub.3 H.sub.7 F NHOCH.sub.35068 H C.sub.3 H.sub.7 F NHOCH.sub.2CHCH.sub.25069 H C.sub.3 H.sub.7 F NHOCH.sub.2CCH5070 H C.sub.3 H.sub.7 F NHOCH.sub.2 -Ph5071 H C.sub.3 H.sub.7 F NHOCH.sub.2CO.sub.2CH.sub.35072 H C.sub.3 H.sub.7 F NHN(CH.sub.3).sub.25073 H C.sub.3 H.sub.7 F NH-2-pyridyl5074 H C.sub.3 H.sub.7 F N(CH.sub.3).sub.25075 H C.sub.3 H.sub.7 F N.sub.35076 H C.sub.3 H.sub.7 F SCH.sub.35077 H C.sub.3 H.sub.7 F S-i-C.sub.3 H.sub.75078 H i-C.sub.3 H.sub.7 F OH5079 H i-C.sub.3 H.sub.7 F OCH.sub.35080 H i-C.sub.3 H.sub.7 F OC.sub.2 H.sub.55081 H i-C.sub.3 H.sub.7 F O(CH.sub.2).sub.2Cl5082 H i-C.sub.3 H.sub.7 F OCH.sub.2SCH.sub.35083 H i-C.sub.3 H.sub. 7 F OCH.sub.2 -Ph5084 H i-C.sub.3 H.sub.7 F O-Ph5085 H i-C.sub.3 H.sub.7 F OCH.sub.2CHCH.sub.25086 H i-C.sub.3 H.sub.7 F OCH.sub.2CCH5087 H i-C.sub.3 H.sub.7 F OCH.sub.2OC.sub.2 H.sub.55088 H i-C.sub.3 H.sub.7 F NH.sub.25089 H i-C.sub.3 H.sub.7 F NHCH.sub.35090 H i-C.sub.3 H.sub.7 F N(CH.sub.3)-Ph5091 H i-C.sub.3 H.sub.7 F NHOH5092 H i-C.sub.3 H.sub.7 F N(CH.sub.3)OH5093 H i-C.sub.3 H.sub.7 F NHOCH.sub.35094 H i-C.sub.3 H.sub.7 F NHOCH.sub.2CHCH.sub.25095 H i-C.sub.3 H.sub.7 F NHOCH.sub.2CCH5096 H i-C.sub.3 H.sub.7 F NHOCH.sub.2 -Ph5097 H i-C.sub.3 H.sub.7 F NHOCH.sub.2CO.sub.2CH.sub.35098 H i-C.sub.3 H.sub.7 F NHN(CH.sub.3).sub.25099 H i-C.sub.3 H.sub.7 F NH-2-pyridyl5100 H i-C.sub.3 H.sub.7 F N(CH.sub.3).sub.25101 H i-C.sub.3 H.sub.7 F N.sub.35102 H i-C.sub.3 H.sub.7 F SCH.sub.35103 H i-C.sub.3 H.sub.7 F S-i-C.sub.3 H.sub.75104 CH.sub.3 H F OH5105 CH.sub.3 H F OCH.sub.35106 CH.sub.3 H F OC.sub.2 H.sub.55107 CH.sub.3 H F O(CH.sub.2).sub.2Cl5108 CH.sub.3 H F OCH.sub.2SCH.sub.35109 CH.sub.3 H F OCH.sub.2 -Ph5110 CH.sub.3 H F O-Ph5111 CH.sub.3 H F OCH.sub.2CHCH.sub.25112 CH.sub.3 H F OCH.sub.2CCH5113 CH.sub.3 H F OCH.sub.2OC.sub.2 H.sub.55114 CH.sub.3 H F NH.sub.25115 CH.sub.3 H F NHCH.sub.35116 CH.sub.3 H F N(CH.sub.3)-Ph5117 CH.sub.3 H F NHOH5118 CH.sub.3 H F N(CH.sub.3)OH5119 CH.sub.3 H F NHOCH.sub.35120 CH.sub.3 H F NHOCH.sub.2CHCH.sub.25121 CH.sub.3 H F NHOCH.sub.2CCH5122 CH.sub.3 H F NHOCH.sub.2 -Ph5123 CH.sub.3 H F NHOCH.sub.2CO.sub.2CH.sub.35124 CH.sub.3 H F NHN(CH.sub.3).sub.25125 CH.sub.3 H F NH-2-pyridyl5126 CH.sub.3 H F N(CH.sub.3).sub.25127 CH.sub.3 H F N.sub.35128 CH.sub.3 H F SCH.sub.35129 CH.sub.3 H F S-i-C.sub.3 H.sub.75130 CH.sub.3 F F OH rac5131 CH.sub.3 F F OCH.sub.3 rac5132 CH.sub.3 F F OC.sub.2 H.sub.5 rac5133 CH.sub.3 F F O(CH.sub.2).sub.2Cl5134 CH.sub.3 F F OCH.sub.2SCH.sub.35135 CH.sub.3 F F OCH.sub.2 -Ph5136 CH.sub.3 F F O-Ph5137 CH.sub.3 F F OCH.sub.2CHCH.sub.25138 CH.sub.3 F F OCH.sub.2CCH5139 CH.sub.3 F F OCH.sub.2OC.sub.2 H.sub.55140 CH.sub.3 F F NH.sub.25141 CH.sub.3 F F NHCH.sub.35142 CH.sub.3 F F N(CH.sub.3)-Ph5143 CH.sub.3 F F NHOH5144 CH.sub.3 F F N(CH.sub.3)OH5145 CH.sub.3 F F NHOCH.sub.35146 CH.sub.3 F F NHOCH.sub.2CHCH.sub.25147 CH.sub.3 F F NHOCH.sub.2CCH5148 CH.sub.3 F F NHOCH.sub.2 -Ph5149 CH.sub.3 F F NHOCH.sub.2CO.sub.2CH.sub.35150 CH.sub.3 F F NHN(CH.sub.3).sub.25151 CH.sub.3 F F NH-2-pyridyl5152 CH.sub.3 F F N(CH.sub.3).sub.25153 CH.sub.3 F F N.sub.35154 CH.sub.3 F F SCH.sub.35155 CH.sub.3 F F S-i-C.sub.3 H.sub.75156a CH.sub.3 CH.sub.3 F OH erythro5156b CH.sub.3 CH.sub.3 F OH threo5157a CH.sub.3 CH.sub.3 F OCH.sub.3 erythro5157b CH.sub.3 CH.sub.3 F OCH.sub.3 threo5158a CH.sub. 3 CH.sub.3 F OC.sub.2 H.sub.5 erythro5158b CH.sub.3 CH.sub.3 F OC.sub.2 H.sub.5 threo5159 CH.sub.3 CH.sub.3 F O(CH.sub.2).sub.2Cl5160 CH.sub.3 CH.sub.3 F OCH.sub.2SCH.sub.35161 CH.sub.3 CH.sub.3 F OCH.sub.2 -Ph5162 CH.sub.3 CH.sub.3 F O-Ph5163 CH.sub.3 CH.sub.3 F OCH.sub.2CHCH.sub.25164 CH.sub.3 CH.sub.3 F OCH.sub.2CCH5165 CH.sub.3 CH.sub.3 F OCH.sub.2OC.sub.2 H.sub.55166 CH.sub.3 CH.sub.3 F NH.sub.25167 CH.sub.3 CH.sub.3 F NHCH.sub.35168 CH.sub.3 CH.sub.3 F N(CH.sub.3)-Ph5169 CH.sub.3 CH.sub.3 F NHOH5170 CH.sub.3 CH.sub.3 F N(CH.sub.3)OH5171 CH.sub.3 CH.sub.3 F NHOCH.sub.35172 CH.sub.3 CH.sub.3 F NHOCH.sub.2CHCH.sub.25173 CH.sub.3 CH.sub.3 F NHOCH.sub.2CCH5174 CH.sub.3 CH.sub.3 F NHOCH.sub.2 -Ph5175 CH.sub.3 CH.sub.3 F NHOCH.sub.2CO.sub.2CH.sub.35176 CH.sub.3 CH.sub.3 F NHN(CH.sub.3).sub.25177 CH.sub.3 CH.sub.3 F NH-2-pyridyl5178a CH.sub.3 CH.sub.3 F N(CH.sub.3).sub.2 erythro5178b CH.sub.3 CH.sub.3 F N(CH.sub.3).sub.2 threo5179 CH.sub.3 CH.sub.3 F N.sub.35180 CH.sub.3 CH.sub.3 F SCH.sub.35181a CH.sub.3 CH.sub.3 F S-i-C.sub.3 H.sub.7 erythro5181b CH.sub.3 CH.sub.3 F S-i-C.sub.3 H.sub.7 threo5182a CH.sub.3 C.sub.2 H.sub.5 F OH erythro5182b CH.sub.3 C.sub.2 H.sub.5 F OH threo5183 CH.sub.3 C.sub.2 H.sub.5 F OCH.sub.35184a CH.sub.3 C.sub.2 H.sub.5 F OC.sub.2 H.sub.5 erythro5184b CH.sub.3 C.sub.2 H.sub.5 F OC.sub.2 H.sub.5 threo5185 CH.sub.3 C.sub.2 H.sub.5 F O(CH.sub.2).sub.2Cl5186 CH.sub.3 C.sub.2 H.sub.5 F OCH.sub.2SCH.sub.35187 CH.sub.3 C.sub.2 H.sub.5 F OCH.sub.2 -Ph5188 CH.sub.3 C.sub.2 H.sub.5 F O-Ph5189 CH.sub.3 C.sub.2 H.sub.5 F OCH.sub.2CHCH.sub.25190 CH.sub.3 C.sub.2 H.sub.5 F OCH.sub.2CCH5191 CH.sub.3 C.sub.2 H.sub.5 F OCH.sub.2OC.sub.2 H.sub.55192 CH.sub.3 C.sub.2 H.sub.5 F NH.sub.25193 CH.sub.3 C.sub.2 H.sub.5 F NHCH.sub.35194 CH.sub.3 C.sub.2 H.sub.5 F N(CH.sub.3)-Ph5195 CH.sub.3 C.sub.2 H.sub.5 F NHOH5196 CH.sub.3 C.sub.2 H.sub.5 F N(CH.sub.3)OH5197 CH.sub.3 C.sub.2 H.sub.5 F NHOCH.sub.35198 CH.sub.3 C.sub.2 H.sub.5 F NHOCH.sub.2CHCH.sub.25199 CH.sub.3 C.sub.2 H.sub.5 F NHOCH.sub.2CCH5200 CH.sub.3 C.sub.2 H.sub.5 F NHOCH.sub.2 -Ph5201 CH.sub.3 C.sub.2 H.sub.5 F NHOCH.sub.2CO.sub.2CH.sub.35202 CH.sub.3 C.sub.2 H.sub. 5 F NHN(CH.sub.3).sub.25203 CH.sub.3 C.sub.2 H.sub.5 F NH-2-pyridyl5204 CH.sub.3 C.sub.2 H.sub.5 F N(CH.sub.3).sub.25205 CH.sub.3 C.sub.2 H.sub.5 F N.sub.35206 CH.sub.3 C.sub.2 H.sub.5 F SCH.sub.35207 CH.sub.3 C.sub.2 H.sub.5 F S-i-C.sub.3 H.sub.75208 CH.sub.3 n-C.sub.3 H.sub.7 F OH5209 CH.sub.3 n-C.sub.3 H.sub.7 F OCH.sub.35210 CH.sub.3 n-C.sub.3 H.sub.7 F OC.sub.2 H.sub.55211 CH.sub.3 n-C.sub.3 H.sub.7 F O(CH.sub.2).sub.2Cl5212 CH.sub.3 n-C.sub.3 H.sub.7 F OCH.sub.2SCH.sub.35213 CH.sub.3 n-C.sub.3 H.sub.7 F OCH.sub.2 -Ph5214 CH.sub.3 n-C.sub.3 H.sub.7 F O-Ph5215 CH.sub.3 n-C.sub.3 H.sub.7 F OCH.sub.2CHCH.sub.25216 CH.sub.3 n-C.sub.3 H.sub.7 F OCH.sub.2CCH5217 CH.sub.3 n-C.sub.3 H.sub.7 F OCH.sub.2OC.sub.2 H.sub.55218 CH.sub.3 n-C.sub.3 H.sub.7 F NH.sub.25219 CH.sub.3 n-C.sub.3 H.sub.7 F NHCH.sub.35220 CH.sub.3 n-C.sub.3 H.sub.7 F N(CH.sub.3)-Ph5221 CH.sub.3 n-C.sub.3 H.sub.7 F NHOH5222 CH.sub.3 n-C.sub.3 H.sub.7 F N(CH.sub.3)OH5223 CH.sub.3 n-C.sub.3 H.sub.7 F NHOCH.sub.35224 CH.sub.3 n-C.sub.3 H.sub.7 F NHOCH.sub.2CHCH.sub.25225 CH.sub.3 n-C.sub.3 H.sub.7 F NHOCH.sub.2CCH5226 CH.sub.3 n-C.sub.3 H.sub.7 F NHOCH.sub.2 -Ph5227 CH.sub.3 n-C.sub.3 H.sub.7 F NHOCH.sub.2CO.sub.2CH.sub.35228 CH.sub.3 n-C.sub.3 H.sub.7 F NHN(CH.sub.3).sub.25229 CH.sub.3 n-C.sub.3 H.sub.7 F NH-2-pyridyl5230 CH.sub.3 n-C.sub.3 H.sub.7 F N(CH.sub.3).sub.25231 CH.sub.3 n-C.sub.3 H.sub.7 F N.sub.35232 CH.sub.3 n-C.sub.3 H.sub.7 F SCH.sub.35233 CH.sub.3 n-C.sub.3 H.sub.7 F S-i-C.sub.3 H.sub.75234 CH.sub.3 i-C.sub.3 H.sub.7 F OH5235 CH.sub.3 i-C.sub.3 H.sub.7 F OCH.sub.35236 CH.sub.3 i-C.sub.3 H.sub.7 F OC.sub.2 H.sub.55237 CH.sub.3 i-C.sub.3 H.sub.7 F O(CH.sub.2).sub.2Cl5238 CH.sub.3 i-C.sub.3 H.sub.7 F OCH.sub.2SCH.sub.35239 CH.sub.3 i-C.sub.3 H.sub.7 F OCH.sub.2 -Ph5240 CH.sub.3 i-C.sub.3 H.sub.7 F O-Ph5241 CH.sub.3 i-C.sub.3 H.sub.7 F OCH.sub.2CHCH.sub.25242 CH.sub.3 i-C.sub.3 H.sub.7 F OCH.sub.2CCH5243 CH.sub.3 i-C.sub.3 H.sub.7 F OCH.sub.2OC.sub.2 H.sub.55244 CH.sub.3 i-C.sub.3 H.sub.7 F NH.sub.25245 CH.sub.3 i-C.sub.3 H.sub.7 F NHCH.sub.35246 CH.sub.3 i-C.sub.3 H.sub.7 F N(CH.sub.3)-Ph5247 CH.sub.3 i-C.sub.3 H.sub.7 F NHOH5248 CH.sub.3 i-C.sub.3 H.sub.7 F N(CH.sub.3)OH5249 CH.sub.3 i-C.sub.3 H.sub.7 F NHOCH.sub.35250 CH.sub.3 i-C.sub.3 H.sub.7 F NHOCH.sub.2CHCH.sub.25251 CH.sub.3 i-C.sub.3 H.sub.7 F NHOCH.sub.2CCH5252 CH.sub.3 i-C.sub.3 H.sub.7 F NHOCH.sub.2 -Ph5253 CH.sub.3 i-C.sub.3 H.sub.7 F NHOCH.sub.2CO.sub.2CH.sub.35254 CH.sub.3 i-C.sub.3 H.sub.7 F NHN(CH.sub.3).sub.25255 CH.sub.3 i-C.sub.3 H.sub.7 F NH-2-pyridyl5256 CH.sub.3 i-C.sub.3 H.sub.7 F N(CH.sub.3).sub.25257 CH.sub.3 i-C.sub.3 H.sub.7 F N.sub.35258 CH.sub.3 i-C.sub.3 H.sub.7 F SCH.sub.35259 CH.sub.3 i-C.sub.3 H.sub.7 F S-i-C.sub.3 H.sub.75260a CH.sub.3 CH.sub.2CHCH.sub.2 F OH erythro5260b CH.sub.3 CH.sub.2CHCH.sub.2 F OH threo5261a CH.sub.3 CH.sub.2CHCH.sub.2 F OCH.sub.3 erythro5261b CH.sub.3 CH.sub.2CHCH.sub.2 F OCH.sub.3 threo5262a CH.sub.3 CH.sub.2CHCH.sub.2 F OC.sub.2 H.sub.5 erythro5262b CH.sub.3 CH.sub.2CHCH.sub.2 F OC.sub.2 H.sub.5 threo5263 CH.sub.3 CH.sub.2CHCH.sub.2 F O(CH.sub.2).sub.2Cl5264 CH.sub.3 CH.sub.2CHCH.sub.2 F OCH.sub.2SCH.sub.35265 CH.sub.3 CH.sub.2CHCH.sub.2 F OCH.sub.2 -Ph5266 CH.sub.3 CH.sub.2CHCH.sub.2 F O-Ph5267 CH.sub.3 CH.sub.2CHCH.sub.2 F OCH.sub.2CHCH.sub.25268 CH.sub.3 CH.sub.2CHCH.sub.2 F OCH.sub.2CCH5269 CH.sub.3 CH.sub.2CHCH.sub.2 F OCH.sub.2OC.sub.2 H.sub.55270 CH.sub.3 CH.sub.2CHCH.sub.2 F NH.sub.25271 CH.sub.3 CH.sub.2CHCH.sub.2 F NHCH.sub.35272 CH.sub.3 CH.sub.2CHCH.sub.2 F N(CH.sub.3)-Ph5273 CH.sub.3 CH.sub.2CHCH.sub.2 F NHOH5274 CH.sub.3 CH.sub.2CHCH.sub.2 F N(CH.sub.3)OH5275 CH.sub.3 CH.sub.2CHCH.sub.2 F NHOCH.sub.35276 CH.sub.3 CH.sub.2CHCH.sub.2 F NHOCH.sub.2 CHCH.sub.25277 CH.sub.3 CH.sub.2CHCH.sub.2 F NHOCH.sub.2CCH5278 CH.sub.3 CH.sub.2CHCH.sub.2 F NHOCH.sub.2 -Ph5279 CH.sub.3 CH.sub.2CHCH.sub.2 F NHOCH.sub.2CO.sub.2CH.sub.35280 CH.sub.3 CH.sub.2CHCH.sub.2 F NHN(CH.sub.3).sub.25281 CH.sub.3 CH.sub.2CHCH.sub.2 F NH-2-pyridyl5282 CH.sub.3 CH.sub.2CHCH.sub.2 F N(CH.sub.3).sub.25283 CH.sub.3 CH.sub.2CHCH.sub.2 F N.sub.35284 CH.sub.3 CH.sub.2CHCH.sub.2 F SCH.sub.35285 CH.sub.3 CH.sub.2CHCH.sub.2 F S-i-C.sub.3 H.sub.75286a CH.sub.3 CH.sub.2CCH F OH erythro5286b CH.sub.3 CH.sub.2CCH F OH threo5287a CH.sub.3 CH.sub.2CCH F OCH.sub.3 erythro5287b CH.sub.3 CH.sub.2C CH F OCH.sub.3 threo5288a CH.sub.3 CH.sub.2CCH F OC.sub.2 H.sub.5 erythro5288b CH.sub.3 CH.sub.2CCH F OC.sub.2 H.sub.5 threo5289 CH.sub.3 CH.sub.2CCH F O(CH.sub.2).sub.2Cl5290 CH.sub.3 CH.sub.2CCH F OCH.sub.2SCH.sub.35291 CH.sub.3 CH.sub.2CCH F OCH.sub.2 -Ph5292 CH.sub.3 CH.sub.2CCH F O-Ph5293 CH.sub.3 CH.sub.2CCH F OCH.sub.2CHCH.sub.25294 CH.sub.3 CH.sub.2CCH F OCH.sub.2CCH5295 CH.sub.3 CH.sub.2 CCH F OCH.sub.2OC.sub.2 H.sub.55296 CH.sub.3 CH.sub.2CCH F NH.sub.25297 CH.sub.3 CH.sub.2CCH F NHCH.sub.35298 CH.sub.3 CH.sub.2CCH F N(CH.sub.3)-Ph5299 CH.sub.3 CH.sub.2CCH F NHOH5300 CH.sub.3 CH.sub.2CCH F N(CH.sub.3)OH5301 CH.sub.3 CH.sub.2CCH F NHOCH.sub.35302 CH.sub.3 CH.sub.2CCH F NHOCH.sub.2CHCH.sub.25303 CH.sub.3 CH.sub.2CCH F NHOCH.sub.2CCH5304 CH.sub.3 CH.sub. 2CCH F NHOCH.sub.2 -Ph5305 CH.sub.3 CH.sub.2CCH F NHOCH.sub.2CO.sub.2CH.sub.35306 CH.sub.3 CH.sub.2CCH F NHN(CH.sub.3).sub.25307 CH.sub.3 CH.sub.2CCH F NH-2-pyridyl5308 CH.sub.3 CH.sub.2CCH F N(CH.sub.3).sub.25309 CH.sub.3 CH.sub.2CCH F N.sub.35310 CH.sub.3 CH.sub.2CCH F SCH.sub.35311 CH.sub.3 CH.sub.2CCH F S-i-C.sub.3 H.sub.75312a CH.sub.3 CH.sub.2 -Ph F OH erythro5312b CH.sub.3 CH.sub.2 -Ph F OH threo5313a CH.sub.3 CH.sub.2 -Ph F OCH.sub.3 erythro5313b CH.sub.3 CH.sub.2 -Ph F OCH.sub.3 threo5314a CH.sub.3 CH.sub.2 -Ph F OC.sub.2 H.sub.5 erythro5314b CH.sub.3 CH.sub.2 -Ph F OC.sub.2 H.sub.5 threo5315 CH.sub.3 CH.sub.2 -Ph F O(CH.sub.2).sub.2Cl5316 CH.sub.3 CH.sub.2 -Ph F OCH.sub.2SCH.sub.35317 CH.sub.3 CH.sub.2 -Ph F OCH.sub.2 -Ph5318 CH.sub.3 CH.sub.2 -Ph F O-Ph5319 CH.sub.3 CH.sub.2 -Ph F OCH.sub.2CHCH.sub.25320 CH.sub.3 CH.sub.2 -Ph F OCH.sub.2CCH5321 CH.sub.3 CH.sub.2 -Ph F OCH.sub.2OC.sub.2 H.sub.55322 CH.sub.3 CH.sub.2 -Ph F NH.sub.25323 CH.sub.3 CH.sub.2 -Ph F NHCH.sub.35324 CH.sub.3 CH.sub.2 -Ph F N(CH.sub.3)-Ph5325 CH.sub.3 CH.sub.2 -Ph F NHOH5326 CH.sub.3 CH.sub.2 -Ph F N(CH.sub.3)OH5327 CH.sub.3 CH.sub.2 -Ph F NHOCH.sub.35328 CH.sub.3 CH.sub.2 -Ph F NHOCH.sub.2CHCH.sub.25329 CH.sub. 3 CH.sub.2 -Ph F NHOCH.sub.2CCH5330 CH.sub.3 CH.sub.2 -Ph F NHOCH.sub.2 -Ph5331 CH.sub.3 CH.sub.2 -Ph F NHOCH.sub.2CO.sub.2CH.sub.35332 CH.sub.3 CH.sub.2 -Ph F NHN(CH.sub.3).sub.25333 CH.sub.3 CH.sub.2 -Ph F NH-2-pyridyl5334 CH.sub.3 CH.sub.2 -Ph F N(CH.sub.3).sub.25335 CH.sub.3 CH.sub.2 -Ph F N.sub.35336 CH.sub.3 Ph F SCH.sub.35337 CH.sub.3 Ph F S-i-C.sub.3 H.sub.75338 CH.sub.3 Ph F OH5339 CH.sub.3 Ph F OCH.sub.35340 CH.sub.3 Ph F OC.sub.2 H.sub.55341 CH.sub.3 Ph F O(CH.sub.2).sub.2Cl5342 CH.sub.3 Ph F OCH.sub.2SCH.sub.35343 CH.sub.3 Ph F OCH.sub.2 -Ph5344 CH.sub.3 Ph F O-Ph5345 CH.sub.3 Ph F OCH.sub.2CHCH.sub.25346 CH.sub.3 Ph F OCH.sub.2CCH5347 CH.sub.3 Ph F OCH.sub.2OC.sub.2 H.sub.55348 CH.sub.3 Ph F NH.sub.25349 CH.sub.3 Ph F NHCH.sub.35350 CH.sub.3 Ph F N(CH.sub.3)-Ph5351 CH.sub.3 Ph F NHOH5352 CH.sub.3 Ph F N(CH.sub.3)OH5353 CH.sub.3 Ph F NHOCH.sub.35354 CH.sub.3 Ph F NHOCH.sub.2CHCH.sub.25355 CH.sub.3 Ph F NHOCH.sub.2CCH5356 CH.sub.3 Ph F NHOCH.sub.2 -Ph5357 CH.sub.3 Ph F NHOCH.sub.2CO.sub.2CH.sub.35358 CH.sub.3 Ph F NHN(CH.sub.3).sub.25359 CH.sub.3 Ph F NH-2-pyridyl5360 CH.sub.3 Ph F N(CH.sub.3).sub.25361 CH.sub.3 Ph F N.sub.35362 CH.sub.3 Ph F SCH.sub.35363 CH.sub.3 Ph F S-i-C.sub.3 H.sub.75364 C.sub.2 H.sub.5 H F OH5365 C.sub.2 H.sub.5 H F OCH.sub.35366 C.sub.2 H.sub.5 H F OC.sub.2 H.sub.55367 C.sub.2 H.sub.5 H F O(CH.sub.2 ).sub.2Cl5368 C.sub.2 H.sub.5 H F OCH.sub.2SCH.sub.35369 C.sub.2 H.sub.5 H F OCH.sub.2 -Ph5370 C.sub.2 H.sub.5 H F O-Ph5371 C.sub.2 H.sub.5 H F OCH.sub.2CHCH.sub.25372 C.sub.2 H.sub.5 H F OCH.sub.2CCH5373 C.sub.2 H.sub.5 H F OCH.sub.2OC.sub.2 H.sub.55374 C.sub.2 H.sub.5 H F NH.sub.25375 C.sub.2 H.sub.5 H F NHCH.sub.35376 C.sub.2 H.sub.5 H F N(CH.sub.3)-Ph5377 C.sub.2 H.sub.5 H F NHOH5378 C.sub.2 H.sub.5 H F N(CH.sub.3)OH5379 C.sub.2 H.sub.5 H F NHOCH.sub.35380 C.sub.2 H.sub.5 H F NHOCH.sub.2CHCH.sub.25381 C.sub.2 H.sub.5 H F NHOCH.sub.2CCH5382 C.sub.2 H.sub.5 H F NHOCH.sub.2 -Ph5383 C.sub.2 H.sub.5 H F NH OCH.sub.2CO.sub.2CH.sub.35384 C.sub.2 H.sub.5 H F NHN(CH.sub.3).sub.25385 C.sub.2 H.sub.5 H F NH-2-pyridyl5386 C.sub.2 H.sub.5 H F N(CH.sub.3).sub.25387 C.sub.2 H.sub.5 H F N.sub.35388 C.sub.2 H.sub.5 H F SCH.sub.35389 C.sub.2 H.sub.5 H F S-i-C.sub.3 H.sub.75390 C.sub.2 H.sub.5 CH.sub.3 F OH5391 C.sub.2 H.sub.5 CH.sub.3 F OCH.sub.35392 C.sub.2 H.sub.5 CH.sub.3 F OC.sub.2 H.sub.55393 C.sub.2 H.sub.5 CH.sub.3 F O(CH.sub.2).sub.2Cl5394 C.sub.2 H.sub.5 CH.sub.3 F OCH.sub.2SCH.sub.35395 C.sub.2 H.sub.5 CH.sub.3 F OCH.sub.2 -Ph5396 C.sub.2 H.sub.5 CH.sub.3 F O-Ph5397 C.sub.2 H.sub.5 CH.sub.3 F OCH.sub.2CHCH.sub.25398 C.sub.2 H.sub.5 CH.sub.3 F OCH.sub.2CCH5399 C.sub.2 H.sub.5 CH.sub.3 F OCH.sub.2OC.sub.2 H.sub.55400 C.sub.2 H.sub.5 CH.sub.3 F NH.sub.25401 C.sub.2 H.sub.5 CH.sub.3 F NHCH.sub.35402 C.sub.2 H.sub.5 CH.sub.3 F N(CH.sub.3)-Ph5403 C.sub.2 H.sub.5 CH.sub.3 F NHOH5404 C.sub.2 H.sub.5 CH.sub.3 F N(CH.sub.3)OH5405 C.sub.2 H.sub.5 CH.sub.3 F NHOCH.sub.35406 C.sub.2 H.sub.5 CH.sub.3 F NHOCH.sub.2CHCH.sub.25407 C.sub.2 H.sub.5 CH.sub.3 F NHOCH.sub.2CCH5408 C.sub.2 H.sub.5 CH.sub.3 F NHOCH.sub.2 -Ph5409 C.sub.2 H.sub.5 CH.sub.3 F NHOCH.sub.2CO.sub.2CH.sub.35410 C.sub.2 H.sub.5 CH.sub.3 F NHN(CH.sub.3).sub.25411 C.sub.2 H.sub.5 CH.sub.3 F NH-2-pyridyl5412 C.sub.2 H.sub.5 CH.sub.3 F N(CH.sub.3).sub.25413 C.sub.2 H.sub.5 CH.sub.3 F N.sub.35414 C.sub.2 H.sub.5 CH.sub.3 F SCH.sub.35415 C.sub.2 H.sub.5 CH.sub.3 F S-i-C.sub.3 H.sub.75416 C.sub.2 H.sub.5 C.sub.2 H.sub.5 F OH5417 C.sub.2 H.sub.5 C.sub.2 H.sub.5 F OCH.sub.35418 C.sub.2 H.sub.5 C.sub.2 H.sub.5 F OC.sub.2 H.sub.55419 C.sub.2 H.sub.5 C.sub.2 H.sub.5 F O(CH.sub.2).sub.2Cl5420 C.sub.2 H.sub.5 C.sub.2 H.sub.5 F OCH.sub.2SCH.sub.35421 C.sub.2 H.sub.5 C.sub.2 H.sub.5 F OCH.sub.2 -Ph5422 C.sub.2 H.sub.5 C.sub.2 H.sub.5 F O-Ph5423 C.sub.2 H.sub.5 C.sub.2 H.sub.5 F OCH.sub.2CHCH.sub.25424 C.sub.2 H.sub.5 C.sub.2 H.sub.5 F OCH.sub.2CCH5425 C.sub.2 H.sub.5 C.sub.2 H.sub.5 F OCH.sub.2OC.sub.2 H.sub.55426 C.sub.2 H.sub.5 C.sub.2 H.sub.5 F NH.sub.25427 C.sub.2 H.sub.5 C.sub.2 H.sub.5 F NHCH.sub.35428 C.sub.2 H.sub.5 C.sub.2 H.sub.5 F N(CH.sub.3)-Ph5429 C.sub.2 H.sub.5 C.sub. 2 H.sub.5 F NHOH5430 C.sub.2 H.sub.5 C.sub.2 H.sub.5 F N(CH.sub.3)OH5431 C.sub.2 H.sub.5 C.sub.2 H.sub.5 F NHOCH.sub.35432 C.sub.2 H.sub.5 C.sub.2 H.sub.5 F NHOCH.sub.2CHCH.sub.25433 C.sub.2 H.sub.5 C.sub.2 H.sub.5 F NHOCH.sub.2CCH5434 C.sub.2 H.sub.5 C.sub.2 H.sub.5 F NHOCH.sub.2 -Ph5435 C.sub.2 H.sub.5 C.sub.2 H.sub.5 F NHOCH.sub.2CO.sub.2CH.sub.35436 C.sub.2 H.sub.5 C.sub.2 H.sub.5 F NHN(CH.sub.3).sub.25437 C.sub.2 H.sub.5 C.sub.2 H.sub.5 F NH-2-pyridyl5438 C.sub.2 H.sub.5 C.sub.2 H.sub.5 F N(CH.sub.3).sub.25439 C.sub.2 H.sub.5 C.sub.2 H.sub.5 F N.sub.35440 C.sub.2 H.sub.5 C.sub.2 H.sub.5 F SCH.sub.35441 C.sub.2 H.sub.5 C.sub.2 H.sub.5 F S-i-C.sub.3 H.sub.75442 C.sub.2 H.sub.5 n-C.sub.3 H.sub.7 F OH5443 C.sub.2 H.sub.5 n-C.sub.3 H.sub.7 F OCH.sub.35444 C.sub.2 H.sub.5 n-C.sub.3 H.sub.7 F OC.sub.2 H.sub.55445 C.sub.2 H.sub.5 n-C.sub.3 H.sub.7 F O(CH.sub.2).sub.2Cl5446 C.sub.2 H.sub.5 n-C.sub.3 H.sub.7 F OCH.sub.2SCH.sub.35447 C.sub.2 H.sub.5 n-C.sub.3 H.sub.7 F OCH.sub.2 -Ph5448 C.sub.2 H.sub.5 n-C.sub.3 H.sub.7 F O-Ph5449 C.sub.2 H.sub.5 n-C.sub.3 H.sub.7 F OCH.sub.2CHCH.sub.25450 C.sub.2 H.sub.5 n-C.sub.3 H.sub.7 F OCH.sub.2CCH5451 C.sub.2 H.sub.5 n-C.sub.3 H.sub.7 F OCH.sub.2OC.sub.2 H.sub.55452 C.sub.2 H.sub.5 n-C.sub.3 H.sub.7 F NH.sub.25453 C.sub.2 H.sub.5 n-C.sub.3 H.sub.7 F NHCH.sub.35454 C.sub.2 H.sub.5 n-C.sub.3 H.sub.7 F N(CH.sub.3)-Ph5455 C.sub.2 H.sub.5 n-C.sub.3 H.sub.7 F NHOH5456 C.sub.2 H.sub.5 n-C.sub.3 H.sub. 7 F N(CH.sub.3)OH5457 C.sub.2 H.sub.5 n-C.sub.3 H.sub.7 F NHOCH.sub.35458 C.sub.2 H.sub.5 n-C.sub.3 H.sub.7 F NHOCH.sub.2CHCH.sub.25459 C.sub.2 H.sub.5 n-C.sub.3 H.sub.7 F NHOCH.sub.2CCH5460 C.sub.2 H.sub.5 n-C.sub.3 H.sub.7 F NHOCH.sub.2 -Ph5461 C.sub.2 H.sub.5 n-C.sub.3 H.sub.7 F NHOCH.sub.2CO.sub.2CH.sub.35462 C.sub.2 H.sub.5 n-C.sub.3 H.sub.7 F NHN(CH.sub.3).sub.25463 C.sub.2 H.sub.5 n-C.sub.3 H.sub.7 F NH-2-pyridyl5464 C.sub.2 H.sub.5 n-C.sub.3 H.sub.7 F N(CH.sub.3).sub.25465 C.sub.2 H.sub.5 n-C.sub.3 H.sub.7 F N.sub.35466 C.sub.2 H.sub.5 n-C.sub.3 H.sub.7 F SCH.sub.35467 C.sub.2 H.sub.5 n-C.sub.3 H.sub.7 F S-i-C.sub.3 H.sub.75468 C.sub.2 H.sub.5 i-C.sub.3 H.sub.7 F OH5469 C.sub.2 H.sub.5 i-C.sub.3 H.sub.7 F OCH.sub.35470 C.sub. 2 H.sub.5 i-C.sub.3 H.sub.7 F OC.sub.2 H.sub.55471 C.sub.2 H.sub.5 i-C.sub.3 H.sub.7 F O(CH.sub.2).sub.2Cl5472 C.sub.2 H.sub.5 i-C.sub.3 H.sub.7 F OCH.sub.2SCH.sub.35473 C.sub.2 H.sub.5 i-C.sub.3 H.sub.7 F OCH.sub.2 -Ph5474 C.sub.2 H.sub.5 i-C.sub.3 H.sub.7 F O-Ph5475 C.sub.2 H.sub.5 i-C.sub.3 H.sub.7 F OCH.sub.2CHCH.sub.25476 C.sub.2 H.sub.5 i-C.sub.3 H.sub.7 F OCH.sub.2CCH5477 C.sub.2 H.sub.5 i-C.sub.3 H.sub.7 F OCH.sub.2OC.sub.2 H.sub.55478 C.sub.2 H.sub.5 i-C.sub.3 H.sub.7 F NH.sub.25479 C.sub.2 H.sub.5 i-C.sub.3 H.sub.7 F NHCH.sub.35480 C.sub.2 H.sub.5 i-C.sub.3 H.sub.7 F N(CH.sub.3)-Ph5481 C.sub.2 H.sub.5 i-C.sub.3 H.sub.7 F NHOH5482 C.sub.2 H.sub.5 i-C.sub.3 H.sub.7 F N(CH.sub.3)OH5483 C.sub.2 H.sub.5 i-C.sub.3 H.sub. 7 F NHOCH.sub.35484 C.sub.2 H.sub.5 i-C.sub.3 H.sub.7 F NHOCH.sub.2CHCH.sub.25485 C.sub.2 H.sub.5 i-C.sub.3 H.sub.7 F NHOCH.sub.2CCH5486 C.sub.2 H.sub.5 i-C.sub.3 H.sub.7 F NHOCH.sub.2 -Ph5487 C.sub.2 H.sub.5 i-C.sub.3 H.sub.7 F NHOCH.sub.2CO.sub.2CH.sub.35488 C.sub.2 H.sub.5 i-C.sub.3 H.sub.7 F NHN(CH.sub.3).sub.25489 C.sub.2 H.sub.5 i-C.sub.3 H.sub.7 F NH-2-pyridyl5490 C.sub.2 H.sub.5 i-C.sub.3 H.sub.7 F N(CH.sub.3).sub.25491 C.sub.2 H.sub.5 i-C.sub.3 H.sub.7 F N.sub.35492 C.sub.2 H.sub.5 i-C.sub.3 H.sub.7 F SCH.sub.35493 C.sub.2 H.sub.5 i-C.sub.3 H.sub.7 F S-i-C.sub.3 H.sub.75494 n-C.sub.3 H.sub.7 H F OH5495 n-C.sub.3 H.sub.7 H F OCH.sub.35496 n-C.sub.3 H.sub.7 H F OC.sub.2 H.sub.55497 n-C.sub.3 H.sub.7 H F O(CH.sub.2 ).sub.2Cl5498 n-C.sub.3 H.sub.7 H F OCH.sub.2SCH.sub.35499 n-C.sub.3 H.sub.7 H F OCH.sub.2 -Ph5500 n-C.sub.3 H.sub.7 H F O-Ph5501 n-C.sub.3 H.sub.7 H F OCH.sub.2CHCH.sub.25502 n-C.sub.3 H.sub.7 H F OCH.sub.2CCH5503 n-C.sub.3 H.sub.7 H F OCH.sub.2OC.sub.2 H.sub.55504 n-C.sub.3 H.sub.7 H F NH.sub.25505 n-C.sub.3 H.sub.7 H F NHCH.sub.35506 n-C.sub.3 H.sub.7 H F N(CH.sub.3)-Ph5507 n-C.sub.3 H.sub.7 H F NHOH5508 n-C.sub.3 H.sub.7 H F N(CH.sub.3)OH5509 n-C.sub.3 H.sub.7 H F NHOCH.sub.35510 n-C.sub.3 H.sub.7 H F NHOCH.sub.2CHCH.sub.25511 n-C.sub.3 H.sub.7 H F NHOCH.sub.2CCH5512 n-C.sub.3 H.sub.7 H F NHOCH.sub.2 -Ph5513 n-C.sub.3 H.sub.7 H F NH OCH.sub.2CO.sub.2CH.sub.35514 n-C.sub.3 H.sub.7 H F NHN(CH.sub.3).sub.25515 n-C.sub.3 H.sub.7 H F NH-2-pyridyl5516 n-C.sub.3 H.sub.7 H F N(CH.sub.3).sub.25517 n-C.sub.3 H.sub.7 H F N.sub.35518 n-C.sub.3 H.sub.7 H F SCH.sub.35519 n-C.sub.3 H.sub.7 H F S-i-C.sub.3 H.sub.75520 n-C.sub.3 H.sub.7 F F OH rac5521 n-C.sub.3 H.sub.7 F F OCH.sub.3 rac5522 n-C.sub.3 H.sub.7 F F OCH.sub.3 rac5523 n-C.sub.3 H.sub.7 F F OC.sub.2 H.sub.55524 n-C.sub.3 H.sub.7 F F O(CH.sub.2).sub.2Cl5525 n-C.sub.3 H.sub.7 F F OCH.sub.2SCH.sub.35526 n-C.sub.3 H.sub.7 F F OCH.sub.2 -Ph5527 n-C.sub.3 H.sub.7 F F O-Ph5528 n-C.sub.3 H.sub.7 F F OCH.sub.2CHCH.sub.25529 n-C.sub.3 H.sub.7 F F OCH.sub.2CCH5530 n-C.sub.3 H.sub.7 F F OCH.sub.2 OC.sub.2 H.sub.55531 n-C.sub.3 H.sub.7 F F NH.sub.25532 n-C.sub.3 H.sub.7 F F NHCH.sub.35533 n-C.sub.3 H.sub.7 F F N(CH.sub.3)-Ph5534 n-C.sub.3 H.sub.7 F F NHOH5535 n-C.sub.3 H.sub.7 F F N(CH.sub.3)OH5536 n-C.sub.3 H.sub.7 F F NHOCH.sub.35537 n-C.sub.3 H.sub.7 F F NHOCH.sub.2CHCH.sub.25538 n-C.sub.3 H.sub.7 F F NHOCH.sub.2CCH5539 n-C.sub.3 H.sub.7 F F NHOCH.sub.2 -Ph5540 n-C.sub.3 H.sub.7 F F NHOCH.sub.2CO.sub.2CH.sub.35541 n-C.sub.3 H.sub.7 F F NHN(CH.sub.3).sub.25542 n-C.sub.3 H.sub.7 F F NH-2-pyridyl5543 n-C.sub.3 H.sub.7 F F N(CH.sub.3).sub.25544 n-C.sub.3 H.sub.7 F F N.sub.35545 n-C.sub.3 H.sub.7 F F SCH.sub.35546 n-C.sub.3 H.sub.7 F F S-i-C.sub.3 H.sub.75547 n-C.sub.3 H.sub.7 CH.sub.3 F OH5548 n-C.sub. 3 H.sub.7 CH.sub.3 F OCH.sub.35549 n-C.sub.3 H.sub.7 CH.sub.3 F OC.sub.2 H.sub.55550 n-C.sub.3 H.sub.7 CH.sub.3 F O(CH.sub.2).sub.2Cl5551 n-C.sub.3 H.sub.7 CH.sub.3 F OCH.sub.2SCH.sub.35552 n-C.sub.3 H.sub.7 CH.sub.3 F OCH.sub.2 -Ph5553 n-C.sub.3 H.sub.7 CH.sub.3 F O-Ph5554 n-C.sub.3 H.sub.7 CH.sub.3 F OCH.sub.2CHCH.sub.25555 n-C.sub.3 H.sub.7 CH.sub.3 F OCH.sub.2CCH5556 n-C.sub.3 H.sub.7 CH.sub.3 F OCH.sub.2OC.sub.2 H.sub.55557 n-C.sub.3 H.sub.7 CH.sub.3 F NH.sub.25558 n-C.sub.3 H.sub.7 CH.sub.3 F NHCH.sub.35559 n-C.sub.3 H.sub.7 CH.sub.3 F N(CH.sub.3)-Ph5560 n-C.sub.3 H.sub.7 CH.sub.3 F NHOH5561 n-C.sub.3 H.sub.7 CH.sub.3 F N(CH.sub.3)OH5562 n-C.sub.3 H.sub.7 CH.sub.3 F NHOCH.sub.35563 n-C.sub.3 H.sub.7 CH.sub.3 F NHOCH.sub. 2CHCH.sub.25564 n-C.sub.3 H.sub.7 CH.sub.3 F NHOCH.sub.2CCH5565 n-C.sub.3 H.sub.7 CH.sub.3 F NHOCH.sub.2 -Ph5566 n-C.sub.3 H.sub.7 CH.sub.3 F NHOCH.sub.2CO.sub.2CH.sub.35567 n-C.sub.3 H.sub.7 CH.sub.3 F NHN(CH.sub.3).sub.25568 n-C.sub.3 H.sub.7 CH.sub.3 F NH-2-pyridyl5569 n-C.sub.3 H.sub.7 CH.sub.3 F N(CH.sub.3).sub.25570 n-C.sub.3 H.sub.7 CH.sub.3 F N.sub.35571 n-C.sub.3 H.sub.7 CH.sub.3 F SCH.sub.35572 n-C.sub.3 H.sub.7 CH.sub.3 F S-i-C.sub.3 H.sub.75573 n-C.sub.3 H.sub.7 C.sub.2 H.sub.5 F OH5574 n-C.sub.3 H.sub.7 C.sub.2 H.sub.5 F OCH.sub.35575 n-C.sub.3 H.sub.7 C.sub.2 H.sub.5 F OC.sub.2 H.sub.55576 n-C.sub.3 H.sub.7 C.sub.2 H.sub.5 F O(CH.sub.2).sub.2Cl5577 n-C.sub.3 H.sub.7 C.sub.2 H.sub.5 F OCH.sub.2SCH.sub.35578 n-C.sub.3 H.sub.7 C.sub. 2 H.sub.5 F OCH.sub.2 -Ph5579 n-C.sub.3 H.sub.7 C.sub.2 H.sub.5 F O-Ph5580 n-C.sub.3 H.sub.7 C.sub.2 H.sub.5 F OCH.sub.2CHCH.sub.25581 n-C.sub.3 H.sub.7 C.sub.2 H.sub.5 F OCH.sub.2CCH5582 n-C.sub.3 H.sub.7 C.sub.2 H.sub.5 F OCH.sub.2OC.sub.2 H.sub.55583 n-C.sub.3 H.sub.7 C.sub.2 H.sub.5 F NH.sub.25584 n-C.sub.3 H.sub.7 C.sub.2 H.sub.5 F NHCH.sub.35585 n-C.sub.3 H.sub.7 C.sub.2 H.sub.5 F N(CH.sub.3)-Ph5586 n-C.sub.3 H.sub.7 C.sub.2 H.sub.5 F NHOH5587 n-C.sub.3 H.sub.7 C.sub.2 H.sub.5 F N(CH.sub.3)OH5588 n-C.sub.3 H.sub.7 C.sub.2 H.sub.5 F NHOCH.sub.35589 n-C.sub.3 H.sub.7 C.sub.2 H.sub.5 F NHOCH.sub.2CHCH.sub.25590 n-C.sub.3 H.sub.7 C.sub.2 H.sub.5 F NHOCH.sub.2CCH5591 n-C.sub.3 H.sub.7 C.sub.2 H.sub.5 F NHOCH.sub.2 -Ph5592 n-C.sub.3 H.sub.7 C.sub.2 H.sub.5 F NHOCH.sub.2CO.sub.2CH.sub.35593 n-C.sub.3 H.sub.7 C.sub.2 H.sub.5 F NHN(CH.sub.3).sub.25594 n-C.sub.3 H.sub.7 C.sub.2 H.sub.5 F NH-2-pyridyl5595 n-C.sub.3 H.sub.7 C.sub.2 H.sub.5 F N(CH.sub.3).sub.25596 n-C.sub.3 H.sub.7 C.sub.2 H.sub.5 F N.sub.35597 n-C.sub.3 H.sub.7 C.sub.2 H.sub.5 F SCH.sub.35598 n-C.sub.3 H.sub.7 C.sub.2 H.sub.5 F S-i-C.sub.3 H.sub.75599 i-C.sub.3 H.sub.7 H F OH5600 i-C.sub.3 H.sub.7 H F OCH.sub.35601 i-C.sub.3 H.sub.7 H F OC.sub.2 H.sub.55602 i-C.sub.3 H.sub.7 H F O(CH.sub.2).sub.2Cl5603 i-C.sub.3 H.sub.7 H F OCH.sub.2SCH.sub.35604 i-C.sub.3 H.sub.7 H F OCH.sub.2 -Ph5605 i-C.sub.3 H.sub.7 H F O-Ph5606 i-C.sub.3 H.sub.7 H F OCH.sub.2CHCH.sub.25607 i-C.sub.3 H.sub.7 H F OCH.sub.2CCH5608 i-C.sub.3 H.sub.7 H F OCH.sub.2OC.sub.2 H.sub.55609 i-C.sub.3 H.sub.7 H F NH.sub.25610 i-C.sub.3 H.sub.7 H F NHCH.sub.35611 i-C.sub.3 H.sub.7 H F N(CH.sub.3)-Ph5612 i-C.sub.3 H.sub.7 H F NHOH5613 i-C.sub.3 H.sub.7 H F N(CH.sub.3)OH5614 i-C.sub.3 H.sub.7 H F NHOCH.sub.35615 i-C.sub.3 H.sub.7 H F NHOCH.sub.2CHCH.sub.25616 i-C.sub.3 H.sub.7 H F NHOCH.sub.2CCH5617 i-C.sub.3 H.sub.7 H F NHOCH.sub.2 -Ph5618 i-C.sub.3 H.sub.7 H F NHOCH.sub.2CO.sub.2CH.sub.35619 i-C.sub.3 H.sub.7 H F NHN(CH.sub.3).sub.25620 i-C.sub.3 H.sub.7 H F NH-2-pyridyl5621 i-C.sub.3 H.sub.7 H F N(CH.sub.3).sub.25622 i-C.sub.3 H.sub.7 H F N.sub.35623 i-C.sub.3 H.sub. 7 H F SCH.sub.35624 i-C.sub.3 H.sub.7 H F S-i-C.sub.3 H.sub.75625 i-C.sub.3 H.sub.7 F F OH rac5626 i-C.sub.3 H.sub.7 F F OCH.sub.3 rac5627 i-C.sub.3 H.sub.7 F F OC.sub.2 H.sub.5 rac5628 i-C.sub.3 H.sub.7 F F O(CH.sub.2).sub.2Cl5629 i-C.sub.3 H.sub.7 F F OCH.sub.2SCH.sub.35630 i-C.sub.3 H.sub.7 F F OCH.sub.2 -Ph5631 i-C.sub.3 H.sub.7 F F O-Ph5632 i-C.sub.3 H.sub.7 F F OCH.sub.2CHCH.sub.25633 i-C.sub.3 H.sub.7 F F OCH.sub.2CCH5634 i-C.sub.3 H.sub.7 F F OCH.sub.2OC.sub.2 H.sub.55635 i-C.sub.3 H.sub.7 F F NH.sub.25636 i-C.sub.3 H.sub.7 F F NHCH.sub.35637 i-C.sub.3 H.sub.7 F F N(CH.sub.3)-Ph5638 i-C.sub.3 H.sub.7 F F NHOH5639 i-C.sub.3 H.sub.7 F F N(CH.sub.3)OH5640 i-C.sub.3 H.sub.7 F F NHOCH.sub.35641 i-C.sub.3 H.sub.7 F F NHOCH.sub.2CHCH.sub.25642 i-C.sub.3 H.sub.7 F F NHOCH.sub.2CCH5643 i-C.sub.3 H.sub.7 F F NHOCH.sub.2 -Ph5644 i-C.sub.3 H.sub.7 F F NHOCH.sub.2CO.sub.2CH.sub.35645 i-C.sub.3 H.sub.7 F F NHN(CH.sub.3).sub.25646 i-C.sub.3 H.sub.7 F F NH-2-pyridyl5647 i-C.sub.3 H.sub.7 F F N(CH.sub.3).sub.25648 i-C.sub.3 H.sub.7 F F N.sub.35649 i-C.sub.3 H.sub.7 F F SCH.sub.35650 i-C.sub.3 H.sub.7 F F S-i-C.sub.3 H.sub.75651a i-C.sub.3 H.sub.7 CH.sub.3 F OH erythro5651b i-C.sub.3 H.sub.7 CH.sub.3 F OH threo5652 i-C.sub.3 H.sub.7 CH.sub.3 F OCH.sub.35653a i-C.sub.3 H.sub.7 CH.sub.3 F OC.sub.2 H.sub.5 erythro5653b i-C.sub.3 H.sub.7 CH.sub.3 F OC.sub.2 H.sub.5 threo5654 i-C.sub.3 H.sub.7 CH.sub.3 F O(CH.sub.2).sub.2 Cl5655 i-C.sub.3 H.sub.7 CH.sub.3 F OCH.sub.2SCH.sub.35656 i-C.sub.3 H.sub.7 CH.sub.3 F OCH.sub.2 -Ph5657 i-C.sub.3 H.sub.7 CH.sub.3 F O-Ph5658 i-C.sub.3 H.sub.7 CH.sub.3 F OCH.sub.2CHCH.sub.25659 i-C.sub.3 H.sub.7 CH.sub.3 F OCH.sub.2CCH5660 i-C.sub.3 H.sub.7 CH.sub.3 F OCH.sub.2OC.sub.2 H.sub.55661 i-C.sub.3 H.sub.7 CH.sub.3 F NH.sub.25662 i-C.sub.3 H.sub.7 CH.sub.3 F NHCH.sub.35663 i-C.sub.3 H.sub.7 CH.sub.3 F N(CH.sub.3)-Ph5664 i-C.sub.3 H.sub.7 CH.sub.3 F NHOH5665 i-C.sub.3 H.sub.7 CH.sub.3 F N(CH.sub.3)OH5666 i-C.sub.3 H.sub.7 CH.sub.3 F NHOCH.sub.35667 i-C.sub.3 H.sub.7 CH.sub.3 F NHOCH.sub.2CHCH.sub.25668 i-C.sub.3 H.sub.7 CH.sub.3 F NHOCH.sub.2CCH5669 i-C.sub.3 H.sub.7 CH.sub.3 F NHOCH.sub.2 -Ph5670 i-C.sub.3 H.sub.7 CH.sub.3 F NHOCH.sub.2CO.sub.2CH.sub.35671 i-C.sub.3 H.sub.7 CH.sub.3 F NHN(CH.sub.3).sub.25672 i-C.sub.3 H.sub.7 CH.sub.3 F NH-2-pyridyl5673 i-C.sub.3 H.sub.7 CH.sub.3 F N(CH.sub.3).sub.25674 i-C.sub.3 H.sub.7 CH.sub.3 F N.sub.35675 i-C.sub.3 H.sub.7 CH.sub.3 F SCH.sub.35676 i-C.sub.3 H.sub.7 CH.sub.3 F S-i-C.sub.3 H.sub.75677 i-C.sub.3 H.sub.7 C.sub.2 H.sub.5 F OH5678 i-C.sub.3 H.sub.7 C.sub.2 H.sub.5 F OCH.sub.35679 i-C.sub.3 H.sub.7 C.sub.2 H.sub.5 F OC.sub.2 H.sub.55680 i-C.sub.3 H.sub.7 C.sub.2 H.sub.5 F O(CH.sub.2).sub.2Cl5681 i-C.sub.3 H.sub.7 C.sub.2 H.sub.5 F OCH.sub.2SCH.sub.35682 i-C.sub.3 H.sub.7 C.sub.2 H.sub.5 F OCH.sub.2 -Ph5683 i-C.sub.3 H.sub.7 C.sub.2 H.sub.5 F O-Ph5684 i-C.sub.3 H.sub.7 C.sub.2 H.sub.5 F OCH.sub.2CHCH.sub.25685 i-C.sub.3 H.sub.7 C.sub.2 H.sub.5 F OCH.sub.2CCH5686 i-C.sub.3 H.sub.7 C.sub.2 H.sub.5 F OCH.sub.2OC.sub.2 H.sub.55687 i-C.sub.3 H.sub.7 C.sub.2 H.sub.5 F NH.sub.25688 i-C.sub.3 H.sub.7 C.sub.2 H.sub.5 F NHCH.sub.35689 i-C.sub.3 H.sub.7 C.sub.2 H.sub.5 F N(CH.sub.3)-Ph5690 i-C.sub.3 H.sub.7 C.sub.2 H.sub.5 F NHOH5691 i-C.sub.3 H.sub.7 C.sub.2 H.sub.5 F N(CH.sub.3)OH5692 i-C.sub.3 H.sub.7 C.sub.2 H.sub.5 F NHOCH.sub.35693 i-C.sub.3 H.sub.7 C.sub.2 H.sub.5 F NHOCH.sub.2CHCH.sub.25694 i-C.sub.3 H.sub.7 C.sub.2 H.sub.5 F NHOCH.sub.2CCH5695 i-C.sub.3 H.sub.7 C.sub.2 H.sub.5 F NHOCH.sub.2 -Ph5696 i-C.sub.3 H.sub.7 C.sub.2 H.sub.5 F NHOCH.sub.2CO.sub.2CH.sub.35697 i-C.sub.3 H.sub.7 C.sub.2 H.sub.5 F NHN(CH.sub.3).sub.25698 i-C.sub.3 H.sub.7 C.sub.2 H.sub.5 F NH-2-pyridyl5699 i-C.sub.3 H.sub.7 C.sub.2 H.sub.5 F N(CH.sub.3).sub.25700 i-C.sub.3 H.sub.7 C.sub.2 H.sub.5 F N.sub.35701 i-C.sub.3 H.sub.7 C.sub.2 H.sub.5 F SCH.sub.35702 i-C.sub.3 H.sub.7 C.sub.2 H.sub.5 F S-i-C.sub.3 H.sub.75703 n-C.sub.4 H.sub.9 H F OH5704 n-C.sub.4 H.sub.9 H F OCH.sub.35705 n-C.sub.4 H.sub.9 H F OC.sub.2 H.sub.55706 n-C.sub.4 H.sub.9 H F O(CH.sub.2).sub.2Cl5707 n-C.sub.4 H.sub.9 H F OCH.sub.2SCH.sub.35708 n-C.sub.4 H.sub.9 H F OCH.sub.2 -Ph5709 n-C.sub.4 H.sub.9 H F OPh5710 n-C.sub.4 H.sub.9 H F OCH.sub.2CHCH.sub.25711 n-C.sub.4 H.sub.9 H F OCH.sub.2CCH5712 n-C.sub.4 H.sub.9 H F OCH.sub.2OC.sub.2 H.sub.55713 n-C.sub.4 H.sub.9 H F NH.sub.25714 n-C.sub.4 H.sub.9 H F NHCH.sub.35715 n-C.sub.4 H.sub.9 H F N(CH.sub.3)-Ph5716 n-C.sub.4 H.sub.9 H F NHOH5717 n-C.sub.4 H.sub.9 H F N(CH.sub.3)OH5718 n-C.sub.4 H.sub.9 H F NHOCH.sub.35719 n-C.sub.4 H.sub.9 H F NHOCH.sub.2CHCH.sub.25720 n-C.sub.4 H.sub.9 H F NHOCH.sub.2CCH5721 n-C.sub.4 H.sub.9 H F NHOCH.sub.2 -Ph5722 n-C.sub.4 H.sub.9 H F NHOCH.sub.2CO.sub.2CH.sub.35723 n-C.sub.4 H.sub.9 H F NHN(CH.sub.3).sub.25724 n-C.sub.4 H.sub.9 H F NH-2-pyridyl5725 n-C.sub.4 H.sub.9 H F N(CH.sub.3).sub.25726 n-C.sub.4 H.sub.9 H F N.sub.35727 n-C.sub.4 H.sub.9 H F SCH.sub.35728 n-C.sub.4 H.sub.9 H F S-i-C.sub.3 H.sub.75729 n-C.sub.4 H.sub.9 CH.sub.3 F OH5730 n-C.sub.4 H.sub.9 CH.sub.3 F OCH.sub.35731 n-C.sub.4 H.sub.9 CH.sub.3 F OC.sub.2 H.sub.55732 n-C.sub.4 H.sub.9 CH.sub.3 F O(CH.sub.2).sub.2Cl5733 n-C.sub.4 H.sub.9 CH.sub.3 F OCH.sub.2SCH.sub.35734 n-C.sub.4 H.sub.9 CH.sub.3 F OCH.sub.2 -Ph5735 n-C.sub.4 H.sub.9 CH.sub.3 F O-Ph5736 n-C.sub.4 H.sub.9 CH.sub.3 F OCH.sub.2CHCH.sub.25737 n-C.sub.4 H.sub.9 CH.sub.3 F OCH.sub.2CCH5738 n-C.sub.4 H.sub.9 CH.sub.3 F OCH.sub.2OC.sub.2 H.sub.55739 n-C.sub.4 H.sub.9 CH.sub.3 F NH.sub.25740 n-C.sub.4 H.sub.9 CH.sub.3 F NHCH.sub.35741 n-C.sub.4 H.sub.9 CH.sub.3 F N(CH.sub.3)-Ph5742 n-C.sub.4 H.sub.9 CH.sub.3 F NHOH5743 n-C.sub.4 H.sub.9 CH.sub.3 F N(CH.sub.3)OH5744 n-C.sub.4 H.sub.9 CH.sub.3 F NHOCH.sub.35745 n-C.sub.4 H.sub.9 CH.sub.3 F NHOCH.sub.2CHCH.sub.25746 n-C.sub. 4 H.sub.9 CH.sub.3 F NHOCH.sub.2CCH5747 n-C.sub.4 H.sub.9 CH.sub.3 F NHOCH.sub.2 -Ph5748 n-C.sub.4 H.sub.9 CH.sub.3 F NHOCH.sub.2CO.sub.2CH.sub.35749 n-C.sub.4 H.sub.9 CH.sub.3 F NHN(CH.sub.3).sub.25750 n-C.sub.4 H.sub.9 CH.sub.3 F NH-2-pyridyl5751 n-C.sub.4 H.sub.9 CH.sub.3 F N(CH.sub.3).sub.25752 n-C.sub.4 H.sub.9 CH.sub.3 F N.sub.35753 n-C.sub.4 H.sub.9 CH.sub.3 F SCH.sub.35754 n-C.sub.4 H.sub.9 CH.sub.3 F S-i-C.sub.3 H.sub.75755 Ph H F OH5756 Ph H F OCH.sub.35757 Ph H F OC.sub.2 H.sub.55758 Ph H F O(CH.sub.2).sub.2Cl5759 Ph H F OCH.sub.2SCH.sub.35760 Ph H F OCH.sub.2 -Ph5761 Ph H F O-Ph5762 Ph H F OCH.sub.2CHCH.sub.25763 Ph H F OCH.sub.2CCH5764 Ph H F OCH.sub.2OC.sub.2 H.sub.55765 Ph H F NH.sub.25766 Ph H F NHCH.sub.35767 Ph H F N(CH.sub.3)-Ph5768 Ph H F NHOH5769 Ph H F N(CH.sub.3)OH5770 Ph H F NHOCH.sub.35771 Ph H F NHOCH.sub.2CHCH.sub.25772 Ph H F NHOCH.sub.2CCH5773 Ph H F NHOCH.sub.2 -Ph5774 Ph H F NHOCH.sub.2CO.sub.2CH.sub.35775 Ph H F NHN(CH.sub.3).sub.25776 Ph H F NH-2-pyridyl5777 Ph H F N(CH.sub.3).sub.25778 Ph H F N.sub.35779 Ph H F SCH.sub.35780 Ph H F S-i-C.sub.3 H.sub.75781a Ph CH.sub.3 F OH erythro5781b Ph CH.sub.3 F OH threo5782 Ph CH.sub.3 F OCH.sub.35783a Ph CH.sub.3 F OC.sub.2 H.sub.5 erythro5783b Ph CH.sub.3 F OC.sub.2 H.sub.5 threo5784 Ph CH.sub.3 F O(CH.sub.2).sub. 2Cl5785 Ph CH.sub.3 F OCH.sub.2SCH.sub.35786 Ph CH.sub.3 F OCH.sub.2 -Ph5787 Ph CH.sub.3 F O-Ph5788 Ph CH.sub.3 F OCH.sub.2CHCH.sub.25789 Ph CH.sub.3 F OCH.sub.2CCH5790 Ph CH.sub.3 F OCH.sub.2OC.sub.2 H.sub.55791 Ph CH.sub.3 F NH.sub.25792 Ph CH.sub.3 F NHCH.sub.35793 Ph CH.sub.3 F N(CH.sub.3)-Ph5794 Ph CH.sub.3 F NHOH5795 Ph CH.sub.3 F N(CH.sub.3)OH5796 Ph CH.sub.3 F NHOCH.sub.35797 Ph CH.sub.3 F NHOCH.sub.2CHCH.sub.25798 Ph CH.sub.3 F NHOCH.sub.2CCH5799 Ph CH.sub.3 F NHOCH.sub.2Ph5800 Ph CH.sub.3 F NHOCH.sub.2CO.sub.2CH.sub.35801 Ph CH.sub.3 F NHN(CH.sub.3).sub.25802 Ph CH.sub.3 F NH-2-pyridyl5803 Ph CH.sub.3 F N(CH.sub.3).sub.25804 Ph CH.sub.3 F N.sub.35805 Ph CH.sub.3 F SCH.sub.35806 Ph CH.sub.3 F S-i-C.sub.3 H.sub.75807 CF.sub.3 F F OH rac5808 CF.sub.3 F F OCH.sub.3 rac5809 CF.sub.3 F F OC.sub.2 H.sub.5 rac5810 CF.sub.3 F F O(CH.sub.2).sub.2Cl5811 CF.sub.3 F F OCH.sub.2SCH.sub.35812 CF.sub.3 F F OCH.sub.2 -Ph5813 CF.sub.3 F F O-Ph5814 CF.sub.3 F F OCH.sub.2CHCH.sub.25815 CF.sub.3 F F OCH.sub.2CCH5816 CF.sub.3 F F OCH.sub.2OC.sub.2 H.sub.55817 CF.sub.3 F F NH.sub.25818 CF.sub.3 F F NHCH.sub.35819 CF.sub.3 F F N(CH.sub.3)-Ph5820 CF.sub.3 F F NHOH5821 CF.sub.3 F F N(CH.sub.3)OH5822 CF.sub.3 F F NHOCH.sub.35823 CF.sub.3 F F NHOCH.sub.2CHCH.sub.25824 CF.sub.3 F F NHOCH.sub.2C CH5825 CF.sub.3 F F NHOCH.sub.2 -Ph5826 CF.sub.3 F F NHOCH.sub.2CO.sub.2CH.sub.35827 CF.sub.3 F F NHN(CH.sub.3).sub.25828 CF.sub.3 F F NH-2-pyridyl5829 CF.sub.3 F F N(CH.sub.3).sub.25830 CF.sub.3 F F N.sub.35831 CF.sub.3 F F SCH.sub.35832 CF.sub.3 F F S-i-C.sub.3 H.sub.75833 CF.sub.3 CH.sub.3 F OH mixture5834 CF.sub.3 CH.sub.3 F OCH.sub.35835 CF.sub.3 CH.sub.3 F OC.sub.2 H.sub.5 mixture5836 CF.sub.3 CH.sub.3 F O(CH.sub.2).sub.2Cl5837 CF.sub.3 CH.sub.3 F OCH.sub.2SCH.sub.35838 CF.sub.3 CH.sub.3 F OCH.sub.2 -Ph5839 CF.sub.3 CH.sub.3 F O-Ph5840 CF.sub.3 CH.sub.3 F OCH.sub.2CHCH.sub.25841 CF.sub.3 CH.sub.3 F OCH.sub.2CCH5842 CF.sub.3 CH.sub.3 F OCH.sub.2OC.sub.2 H.sub.55843 CF.sub. 3 CH.sub.3 F NH.sub.25844 CF.sub.3 CH.sub.3 F NHCH.sub.35845 CF.sub.3 CH.sub.3 F N(CH.sub.3)-Ph5846 CF.sub.3 CH.sub.3 F NHOH5847 CF.sub.3 CH.sub.3 F N(CH.sub.3)OH5848 CF.sub.3 CH.sub.3 F NHOCH.sub.35849 CF.sub.3 CH.sub.3 F NHOCH.sub.2CHCH.sub.25850 CF.sub.3 CH.sub.3 F NHOCH.sub.2CCH5851 CF.sub.3 CH.sub.3 F NHOCH.sub.2 -Ph5852 CF.sub.3 CH.sub.3 F NHOCH.sub.2CO.sub.2CH.sub.35853 CF.sub.3 CH.sub.3 F NHN(CH.sub.3).sub.25854 CF.sub.3 CH.sub.3 F NH-2-pyridyl5855 CF.sub.3 CH.sub.3 F N(CH.sub.3).sub.25856 CF.sub.3 CH.sub.3 F N.sub.35857 CF.sub.3 CH.sub.3 F SCH.sub.35858 CF.sub.3 CH.sub.3 F S-i-C.sub.3 H.sub.75859 CF.sub.3 CH.sub.2CHCH.sub.2 F OH5860 CF.sub.3 CH.sub.2CHCH.sub.2 F OCH.sub.35861 CF.sub.3 CH.sub.2CHCH.sub.2 F OC.sub.2 H.sub.55862 CF.sub.3 CH.sub.2CHCH.sub.2 F O(CH.sub.2).sub.2Cl5863 CF.sub.3 CH.sub.2CHCH.sub.2 F OCH.sub.2SCH.sub.35864 CF.sub.3 CH.sub.2CHCH.sub.2 F OCH.sub.2 -Ph5865 CF.sub.3 CH.sub.2CHCH.sub.2 F O-Ph5866 CF.sub.3 CH.sub.2CHCH.sub.2 F OCH.sub.2CHCH.sub.25867 CF.sub.3 CH.sub.2CHCH.sub.2 F OCH.sub.2CCH5868 CF.sub.3 CH.sub.2CHCH.sub.2 F OCH.sub.2OC.sub.2 H.sub.55869 CF.sub.3 CH.sub.2CHCH.sub.2 F NH.sub.25870 CF.sub.3 CH.sub.2CHCH.sub.2 F NHCH.sub.35871 CF.sub.3 CH.sub.2CHCH.sub.2 F N(CH.sub.3)-Ph5872 CF.sub.3 CH.sub.2CHCH.sub.2 F NHOH5873 CF.sub.3 CH.sub.2CHCH.sub.2 F N(CH.sub.3)OH5874 CF.sub.3 CH.sub.2CHCH.sub.2 F NHOCH.sub.35875 CF.sub.3 CH.sub.2CHCH.sub.2 F NHOCH.sub.2CHCH.sub.25876 CF.sub. 3 CH.sub.2CHCH.sub.2 F NHOCH.sub.2CCH5877 CF.sub.3 CH.sub.2CHCH.sub.2 F NHOCH.sub.2 -Ph5878 CF.sub.3 CH.sub.2CHCH.sub.2 F NHOCH.sub.2CO.sub.2CH.sub.35879 CF.sub.3 CH.sub.2CHCH.sub.2 F NHN(CH.sub.3).sub.25880 CF.sub.3 CH.sub.2CHCH.sub.2 F NH-2-pyridyl5881 CF.sub.3 CH.sub.2CHCH.sub.2 F N(CH.sub.3).sub.25882 CF.sub.3 CH.sub.2CHCH.sub.2 F N.sub.35883 CF.sub.3 CH.sub.2CHCH.sub.2 F SCH.sub.35884 CF.sub.3 CH.sub.2CHCH.sub.2 F S-i-C.sub.3 H.sub.75885 CF.sub.3 CH.sub.2CCH F OH5886 CF.sub.3 CH.sub.2CCH F OCH.sub.35887 CF.sub.3 CH.sub.2CCH F OC.sub.2 H.sub.55888 CF.sub.3 CH.sub.2C CH F O(CH.sub.2).sub.2Cl5889 CF.sub.3 CH.sub.2CCH F OCH.sub.2SCH.sub.35890 CF.sub.3 CH.sub.2CCH F OCH.sub.2 -Ph5891 CF.sub.3 CH.sub.2CCH F O-Ph5892 CF.sub.3 CH.sub.2CCH F OCH.sub.2CHCH.sub.25893 CF.sub.3 CH.sub.2CCH F OCH.sub.2CCH5894 CF.sub.3 CH.sub.2CCH F OCH.sub.2OC.sub.2 H.sub.55895 CF.sub.3 CH.sub.2CCH F NH.sub.25896 CF.sub.3 CH.sub.2CCH F NHCH.sub.35897 CF.sub.3 CH.sub.2C CH F N(CH.sub.3)-Ph5898 CF.sub.3 CH.sub.2CCH F NHOH5899 CF.sub.3 CH.sub.2CCH F N(CH.sub.3)OH5900 CF.sub.3 CH.sub.2CCH F NHOCH.sub.35901 CF.sub.3 CH.sub.2CCH F NHOCH.sub.2CHCH.sub.25902 CF.sub.3 CH.sub.2CCH F NHOCH.sub.2CCH5903 CF.sub.3 CH.sub.2CCH F NHOCH.sub.2 -Ph5904 CF.sub.3 CH.sub.2CCH F NHOCH.sub.2CO.sub.2CH.sub.35905 CF.sub.3 CH.sub.2CCH F NHN(CH.sub.3).sub.25906 CF.sub.3 CH.sub.2 CCH F NH-2-pyridyl5907 CF.sub.3 CH.sub.2CCH F N(CH.sub.3).sub.25908 CF.sub.3 CH.sub.2CCH F N.sub.35909 CF.sub.3 CH.sub.2CCH F SCH.sub.35910 CF.sub.3 CH.sub.2CCH F S-i-C.sub.3 H.sub.75911 CF.sub.3 CH.sub.2 -Ph F OH5912 CF.sub.3 CH.sub.2 -Ph F OCH.sub.35913 CF.sub.3 CH.sub.2 -Ph F OC.sub.2 H.sub.55914 CF.sub.3 CH.sub.2 -Ph F O(CH.sub.2).sub.2Cl5915 CF.sub.3 CH.sub.2 -Ph F OCH.sub.2SCH.sub.35916 CF.sub.3 CH.sub.2 -Ph F OCH.sub.2 -Ph5917 CF.sub.3 CH.sub.2 -Ph F O-Ph5918 CF.sub.3 CH.sub.2 -Ph F OCH.sub.2CHCH.sub.25919 CF.sub.3 CH.sub.2 -Ph F OCH.sub.2C CH5920 CF.sub.3 CH.sub.2 -Ph F OCH.sub.2OC.sub.2 H.sub.55921 CF.sub.3 CH.sub.2 -Ph F NH.sub.25922 CF.sub.3 CH.sub.2 -Ph F NHCH.sub.35923 CF.sub.3 CH.sub.2 -Ph F N(CH.sub.3)-Ph5924 CF.sub.3 CH.sub.2 -Ph F NHOH5925 CF.sub.3 CH.sub.2 -Ph F N(CH.sub.3)OH5926 CF.sub.3 CH.sub.2 -Ph F NHOCH.sub.35927 CF.sub.3 CH.sub.2 -Ph F NHOCH.sub.2CHCH.sub.25928 CF.sub.3 CH.sub.2 -Ph F NHOCH.sub.2CCH5929 CF.sub.3 CH.sub.2 -Ph F NHOCH.sub.2 -Ph5930 CF.sub.3 CH.sub.2 -Ph F NHOCH.sub.2CO.sub.2CH.sub.35931 CF.sub.3 CH.sub.2 -Ph F NHN(CH.sub.3).sub.25932 CF.sub.3 CH.sub.2 -Ph F NH-2-pyridyl5933 CF.sub.3 CH.sub.2 -Ph F N(CH.sub.3).sub.25934 CF.sub.3 CH.sub.2 -Ph F N.sub.35935 CF.sub.3 CH.sub.2 -Ph F SCH.sub.35936 CF.sub.3 CH.sub.2 -Ph F S-i-C.sub.3 H.sub.75937 CH.sub.3 CF.sub.3 F OH5938 CH.sub.3 CF.sub.3 F OH5939 CH.sub.3 CF.sub.3 F OCH.sub.35940 CH.sub.3 CF.sub.3 F OCH.sub.35941 CH.sub.3 CF.sub.3 F OC.sub.2 H.sub.55942 CH.sub.3 CF.sub.3 F OC.sub.2 H.sub.55943 CH.sub.3 CF.sub.3 F O(CH.sub.2).sub.2Cl5944 CH.sub.3 CF.sub.3 F OCH.sub.2SCH.sub.35945 CH.sub.3 CF.sub.3 F OCH.sub.2 -Ph5946 CH.sub.3 CF.sub.3 F O-Ph5947 CH.sub.3 CF.sub.3 F OCH.sub.2CHCH.sub.25948 CH.sub.3 CF.sub.3 F OCH.sub.2CCH5949 CH.sub.3 CF.sub.3 F OCH.sub.2OC.sub.2 H.sub.55950 CH.sub.3 CF.sub.3 F NH.sub.25951 CH.sub.3 CF.sub.3 F NHCH.sub.35952 CH.sub.3 CF.sub.3 F N(CH.sub.3)-Ph5953 CH.sub.3 CF.sub.3 F NHOH5954 CH.sub.3 CF.sub.3 F N(CH.sub.3)OH5955 CH.sub.3 CF.sub.3 F NHOCH.sub.35956 CH.sub.3 CF.sub.3 F NHOCH.sub.2CHCH.sub.25957 CH.sub.3 CF.sub.3 F NHOCH.sub.2CCH5958 CH.sub.3 CF.sub.3 F NHOCH.sub.2 -Ph5959 CH.sub.3 CF.sub.3 F NHOCH.sub.2CO.sub.2CH.sub.35960 CH.sub.3 CF.sub.3 F NHN(CH.sub.3).sub.25961 CH.sub.3 CF.sub.3 F NH-2-pyridyl5962 CH.sub.3 CF.sub.3 F N(CH.sub.3).sub.25963 CH.sub.3 CF.sub.3 F SCH.sub.35964 CH.sub.3 CF.sub.3 F S-i-C.sub.3 H.sub.75965 CO.sub.2 H CH.sub.3 F OH mixture5966 CO.sub.2CH.sub.3 CH.sub.3 F OCH.sub.35967 CO.sub.2C.sub.2 H.sub.5 CH.sub.3 F OC.sub.2 H.sub.5 mixture__________________________________________________________________________
TABLE 6__________________________________________________________________________ ##STR26##CompoundNo. R.sub.3 R.sub.4 X Y Remarks__________________________________________________________________________6001 CH.sub.2 OCH.sub.2 F OH mixture6002 CH.sub.2 OCH.sub.2 F OCH.sub.36003 CH.sub.2 OCH.sub.2 F OC.sub.2 H.sub.5 mixture6004 CH.sub.2 OCH.sub.2 F O-i-C.sub.3 H.sub.76005 CH.sub.2 OCH.sub.2 F O(CH.sub.2).sub.2 Cl6006 CH.sub.2 OCH.sub.2 F OCH.sub.2 SCH.sub.36007 CH.sub.2 OCH.sub.2 F OCH.sub.2 Ph6008 CH.sub.2 OCH.sub.2 F OPh6009 CH.sub.2 OCH.sub.2 F OCH.sub.2 CHCH.sub.26010 CH.sub.2 OCH.sub.2 F OCH.sub.2 CCH6011 CH.sub.2 OCH.sub.2 F OCH.sub.2 OC.sub.2 H.sub.56012 CH.sub.2 OCH.sub.2 F NH.sub.26013 CH.sub.2 OCH.sub.2 F NHCH.sub.36014 CH.sub.2 OCH.sub.2 F N(CH.sub.3)Ph6015 CH.sub.2 OCH.sub.2 F NHOH6016 CH.sub.2 OCH.sub.2 F N(CH.sub.3)OH6017 CH.sub.2 OCH.sub.2 F NHOCH.sub.36018 CH.sub.2 OCH.sub.2 F NHOCH.sub.2 CHCH.sub.26019 CH.sub.2 OCH.sub.2 F NHOCH.sub.2 CCH6020 CH.sub.2 OCH.sub.2 F NH OCH.sub.2 Ph6021 CH.sub.2 OCH.sub.2 F NHOCH.sub.2 CO.sub.2 CH.sub.36022 CH.sub.2 OCH.sub.2 F NHN(CH.sub.3).sub.26023 CH.sub.2 OCH.sub.2 F NH-2-pyridyl6024 CH.sub.2 OCH.sub.2 F NH-2-thiadiazoly6025 CH.sub.2 OCH.sub.2 F N.sub.36026 CH.sub.2 OCH.sub.2 F SCH.sub.36027 CH.sub.2 OCH.sub.2 F SC.sub.2 H.sub.56028 (CH.sub.2).sub.2 O F OH6029 (CH.sub.2).sub.2 O F OCH.sub.36030 (CH.sub.2).sub.2 O F OC.sub.2 H.sub.56031 (CH.sub.2).sub.2 O F O-i-C.sub.3 H.sub.76032 (CH.sub.2).sub.2 O F O(CH.sub.2).sub.2Cl6033 (CH.sub.2).sub.2 O F OCH.sub.2 SCH.sub.36034 (CH.sub.2).sub. 2 O F OCH.sub.2 Ph6035 (CH.sub.2).sub.2 O F OPh6036 (CH.sub.2).sub.2 O F OCH.sub.2 CHCH.sub.26037 (CH.sub.2).sub.2 O F OCH.sub.2 CCH6038 (CH.sub.2).sub.2 O F OCH.sub.2 OC.sub.2 H.sub.56039 (CH.sub.2).sub.2 O F NH.sub.26040 (CH.sub.2).sub.2 O F NHCH.sub.36041 (CH.sub.2).sub.2 O F N(CH.sub.3)Ph6042 (CH.sub.2).sub.2 O F NHOH6043 (CH.sub.2).sub.2 O F N(CH.sub.3)OH6044 (CH.sub.2).sub.2 O F NHOCH.sub.36045 (CH.sub.2).sub.2 O F NHOCH.sub.2 CHCH.sub.26046 (CH.sub.2).sub.2 O F NHOCHCCH6047 (CH.sub.2).sub.2 O F NHOCH.sub.2 Ph6048 (CH.sub.2).sub.2 O F NHOCH.sub.2 CO.sub.2 CH.sub.36049 (CH.sub.2).sub.2 O F NHN(CH.sub.3).sub.26050 (CH.sub.2).sub.2 O F NH-2-pyridyl6051 (CH.sub.2).sub.2 O F NH-2-thiadiazoly6052 (CH.sub.2).sub.2 O F N.sub.36053 (CH.sub.2).sub.2 O F SCH.sub.36054 (CH.sub.2).sub.2 O F SC.sub.2 H.sub.56055 CH.sub.2 O(CH.sub.2).sub.2 F OH6056 CH.sub.2 O(CH.sub.2).sub.2 F OCH.sub.36057 CH.sub.2 O(CH.sub.2).sub.2 F OC.sub.2 H.sub.56058 CH.sub.2 O(CH.sub.2).sub.2 F O-i-C.sub.3 H.sub.76059 CH.sub.2 O(CH.sub.2).sub.2 F O(CH.sub.2).sub.2 Cl6060 CH.sub.2 O(CH.sub.2).sub.2 F OCH.sub.2 SCH.sub.36061 CH.sub.2 O(CH.sub.2).sub.2 F OCH.sub.2 Ph6062 CH.sub.2 O(CH.sub.2).sub.2 F OPh6063 CH.sub.2 O(CH.sub.2).sub.2 F OCH.sub.2 CHCH.sub.26064 CH.sub.2 O(CH.sub.2).sub.2 F OCH.sub.2 CCH6065 CH.sub.2 O(CH.sub.2).sub.2 F OCH.sub.2 OC.sub.2 H.sub.56066 CH.sub.2 O(CH.sub.2).sub.2 F NH.sub.26067 CH.sub.2 O(CH.sub.2).sub.2 F NHCH.sub.36068 CH.sub.2 O(CH.sub.2).sub.2 F N(CH.sub.3)Ph6069 CH.sub.2 O(CH.sub.2).sub.2 F NHOH6070 CH.sub.2 O(CH.sub.2).sub.2 F N(CH.sub.3)OH6071 CH.sub.2 O(CH.sub.2).sub.2 F NHOCH.sub.36072 CH.sub.2 O(CH.sub. 2).sub.2 F NHOCH.sub.2 CHCH.sub.26073 CH.sub.2 O(CH.sub.2).sub.2 F NHOCH.sub.2 CCH6074 CH.sub.2 O(CH.sub.2).sub.2 F NHOCH.sub.2 Ph6075 CH.sub.2 O(CH.sub.2).sub.2 F NHOCH.sub.2 CO.sub.2 CH.sub.36076 CH.sub.2 O(CH.sub.2).sub.2 F NHN(CH.sub.3).sub.26077 CH.sub.2 O(CH.sub.2).sub.2 F NH-2-pyridyl6078 CH.sub.2 O(CH.sub.2).sub.2 F NH-2-thiadiazoly6079 CH.sub.2 O(CH.sub.2).sub.2 F N.sub.36080 CH.sub.2 O(CH.sub.2).sub.2 F SCH.sub.36081 CH.sub.2 O(CH.sub.2).sub.2 F SC.sub.2 H.sub.56082a (CH.sub.2).sub.2 OCH.sub.2 F OH cis6082b (CH.sub.2).sub.2 OCH.sub.2 F OH trans6083 (CH.sub.2).sub.2 OCH.sub.2 F OCH.sub.36084a (CH.sub.2).sub.2 OCH.sub.2 F OC.sub.2 H.sub.5 cis6084b (CH.sub.2).sub.2 OCH.sub.2 F OC.sub.2 H.sub.5 trans6085a (CH.sub.2).sub.2 OCH.sub.2 F O-i-C.sub.3 H.sub.7 cis6085b (CH.sub.2).sub.2 OCH.sub.2 F O-i-C.sub.3 H.sub.7 trans6086 (CH.sub.2).sub.2 OCH.sub.2 F O(CH.sub.2).sub.2 Cl6087 (CH.sub.2).sub.2 OCH.sub.2 F OCH.sub.2 SCH.sub.36088 (CH.sub.2).sub.2 OCH.sub.2 F OCH.sub.2 Ph6089 (CH.sub.2).sub.2 OCH.sub.2 F OPh6090a (CH.sub.2).sub.2 OCH.sub.2 F OCH.sub.2 CHCH.sub.2 cis6090b (CH.sub.2).sub.2 OCH.sub.2 F OCH.sub. 2 CHCH.sub.2 trans6091a (CH.sub.2).sub.2 OCH.sub.2 F OCH.sub.2 CCH cis6091b (CH.sub.2).sub.2 OCH.sub.2 F OCH.sub.2 CCH trans6092 (CH.sub.2).sub.2 OCH.sub.2 F OCH.sub.2 OC.sub.2 H.sub.56093 (CH.sub.2).sub.2 OCH.sub.2 F NH.sub.26094 (CH.sub.2).sub.2 OCH.sub.2 F NHCH.sub.36095 (CH.sub.2).sub.2 OCH.sub.2 F N(CH.sub.3)Ph6096 (CH.sub.2).sub.2 OCH.sub.2 F NHOH6097 (CH.sub.2).sub.2 OCH.sub.2 F N(CH.sub.3)OH6098 (CH.sub.2).sub.2 OCH.sub.2 F NHOCH.sub.36099 (CH.sub.2).sub.2 OCH.sub.2 F NHOCH.sub.2 CHCH.sub.26100 (CH.sub.2).sub.2 OCH.sub.2 F NHO CH.sub.2 CCH6101 (CH.sub.2).sub.2 OCH.sub.2 F NHOCH.sub.2 Ph6102 (CH.sub.2).sub.2 OCH.sub.2 F NHOCH.sub.2 CO.sub.2 CH.sub.36103 (CH.sub.2).sub.2 OCH.sub.2 F NHN(CH.sub.3).sub.26104 (CH.sub.2).sub.2 OCH.sub.2 F NH-2-pyridyl6105 (CH.sub.2).sub.2 OCH.sub.2 F NH-2-thiadiazoly6106 (CH.sub.2).sub.2 OCH.sub.2 F N.sub.36107 (CH.sub.2).sub.2 OCH.sub.2 F SCH.sub.36108 (CH.sub.2).sub.2 OCH.sub.2 F SC.sub.2 H.sub.56109 (CH.sub.2).sub.3 O F OH6110 (CH.sub.2).sub.3 O F OCH.sub.36111 (CH.sub.2).sub.3 O F OC.sub.2 H.sub.56112 (CH.sub.2).sub.3 O F O-i-C.sub.3 H.sub.76113 (CH.sub.2).sub. 3 O F O(CH.sub.2).sub.2 Cl6114 (CH.sub.2).sub.3 O F OCH.sub.2 SCH.sub.36115 (CH.sub.2).sub.3 O F OCH.sub.2 Ph6116 (CH.sub.2).sub.3 O F OPh6117 (CH.sub.2).sub.3 O F OCH.sub.2 CHCH.sub.26118 (CH.sub.2).sub.3 O F OCH.sub.2 CCH6119 (CH.sub.2).sub.3 O F OCH.sub.2 OC.sub.2 H.sub.56120 (CH.sub.2).sub.3 O F NH.sub.26121 (CH.sub.2).sub.3 O F NHCH.sub.36122 (CH.sub.2).sub.3 O F N(CH.sub.3)Ph6123 (CH.sub.2).sub.3 O F NHOH6124 (CH.sub.2).sub.3 O F N(CH.sub.3)OH6125 (CH.sub.2).sub.3 O F NHOCH.sub.36126 (CH.sub.2).sub.3 O F NHOCH.sub. 2 CHCH.sub.26127 (CH.sub.2).sub.3 O F NHOCH.sub.2 CCH6128 (CH.sub.2).sub.3 O F NHOCH.sub.2 Ph6129 (CH.sub.2).sub.3 O F NHOCH.sub.2 CO.sub.2 CH.sub.36130 (CH.sub.2).sub.3 O F NHN(CH.sub.3).sub.26131 (CH.sub.2).sub.3 O F NH-2-pyridyl6132 (CH.sub.2).sub.3 O F NH-2-thiadiazoly6133 (CH.sub.2).sub.3 O F N.sub.36134 (CH.sub.2).sub.3 O F SCH.sub.36135 (CH.sub.2).sub.3 O F SC.sub.2 H.sub.56136a CH.sub.2 SCH.sub.2 F OH cis6136b CH.sub.2 SCH.sub.2 F OH trans6137a CH.sub.2 SCH.sub.2 F OCH.sub.3 cis6137b CH.sub.2 SCH.sub.2 F OCH.sub.3 trans6138 CH.sub.2 SCH.sub.2 F OC.sub.2 H.sub.56139 CH.sub.2 SCH.sub.2 F O-i-C.sub.3 H.sub.76140 CH.sub.2 SCH.sub.2 F O(CH.sub.2).sub.2Cl6141 CH.sub.2 SCH.sub.2 F OCH.sub.2 SCH.sub.36142 CH.sub.2 SCH.sub.2 F OCH.sub.2 Ph6143 CH.sub.2 SCH.sub.2 F OPh6144 CH.sub.2 SCH.sub.2 F OCH.sub.2 CHCH.sub.26145 CH.sub.2 SCH.sub.2 F OCH.sub.2 CCH6146 CH.sub.2 SCH.sub.2 F OCH.sub.2 OC.sub.2 H.sub.56147 CH.sub.2 SCH.sub.2 F NH.sub.26148 CH.sub.2 SCH.sub.2 F NHCH.sub.36149 CH.sub.2 SCH.sub.2 F N(CH.sub.3)Ph6150 CH.sub.2 SCH.sub.2 F NHOH6151 CH.sub.2 SCH.sub.2 F N(CH.sub.3)OH6152 CH.sub.2 SCH.sub.2 F NHOCH.sub.36153 CH.sub.2 SCH.sub.2 F NHOCH.sub.2 CHCH.sub.26154 CH.sub.2 SCH.sub.2 F NHOCH.sub.2 CCH6155 CH.sub.2 SCH.sub.2 F NHOCH.sub.2 Ph6156 CH.sub.2 SCH.sub.2 F NHOCH.sub.2 CO.sub.2 CH.sub.36157 CH.sub.2 SCH.sub.2 F NHN(CH.sub.3).sub.26158 CH.sub.2 SCH.sub.2 F NH-2-pyridyl6159 CH.sub.2 SCH.sub.2 F NH-2-tiadiazoly6160 CH.sub.2 SCH.sub.2 F N.sub.36161 CH.sub.2 SCH.sub.2 F SCH.sub.36162 CH.sub.2 SCH.sub.2 F SC.sub.2 H.sub.56163 (CH.sub.2).sub.2 S F OH6164 (CH.sub.2).sub.2 S F OC.sub.2 H.sub.56165 (CH.sub.2).sub.2 S F O-i-C.sub.3 H.sub.76166 (CH.sub.2).sub.2 S F O(CH.sub.2).sub.2 Cl6167 (CH.sub.2).sub.2 S F OCH.sub.2 SCH.sub.36168 (CH.sub.2).sub.2 S F OCH.sub.2 Ph6169 (CH.sub.2).sub.2 S F OPh6170 (CH.sub.2).sub.2 S F OCH.sub.2 CHCH.sub.26171 (CH.sub.2).sub.2 S F OCH.sub.2 CCH6172 (CH.sub.2).sub.2 S F OCH.sub.2 OC.sub.2 H.sub.56173 (CH.sub.2).sub.2 S F NH.sub.26174 (CH.sub.2).sub.2 S F NHCH.sub.36175 (CH.sub.2).sub.2 S F N(CH.sub.3)Ph6176 (CH.sub.2).sub.2 S F NHOH6177 (CH.sub.2 ).sub.2 S F N(CH.sub.3)OH6178 (CH.sub.2).sub.2 S F NHOCH.sub.36179 (CH.sub.2).sub.2 S F NHOCH.sub.2 CHCH.sub.26180 (CH.sub.2).sub.2 S F NHOCH.sub.2 CCH6181 (CH.sub.2).sub.2 S F NHOCH.sub.2 Ph6182 (CH.sub.2).sub.2 S F NHOCH.sub.2 CO.sub.2 CH.sub.36183 (CH.sub.2).sub.2 S F NHN(CH.sub.3).sub.26184 (CH.sub.2).sub.2 S F NH-2-pyridyl6185 (CH.sub.2).sub.2 S F NH-2-thiadiazoly6186 (CH.sub.2).sub.2 S F N.sub.36187 (CH.sub.2).sub.2 S F SCH.sub.36188 (CH.sub.2).sub.2 S F SC.sub.2 H.sub.56189 CH.sub.2 S(CH.sub.2).sub.2 F OH6190 CH.sub.2 S(CH.sub.2).sub.2 F O CH.sub.36191 CH.sub.2 S(CH.sub.2).sub.2 F OC.sub.2 H.sub.56192 CH.sub.2 S(CH.sub.2).sub.2 F O-i-C.sub.3 H.sub.76193 CH.sub.2 S(CH.sub.2).sub.2 F O(CH.sub.2).sub.2 Cl6194 CH.sub.2 S(CH.sub.2).sub.2 F OCH.sub.2 SCH.sub.36195 CH.sub.2 S(CH.sub.2).sub.2 F OCH.sub.2 Ph6196 CH.sub.2 S(CH.sub.2).sub.2 F OPh6197 CH.sub.2 S(CH.sub.2).sub.2 F OCH.sub.2 CHCH.sub.26198 CH.sub.2 S(CH.sub.2).sub.2 F OCH.sub.2 CCH6199 CH.sub.2 S(CH.sub.2).sub.2 F OCH.sub.2 OC.sub.2 H.sub.56200 CH.sub.2 S(CH.sub.2).sub.2 F NH.sub.26201 CH.sub.2 S(CH.sub.2).sub.2 F NH CH.sub.36202 CH.sub.2 S(CH.sub.2).sub.2 F N(CH.sub.3)Ph6203 CH.sub.2 S(CH.sub.2).sub.2 F NHOH6204 CH.sub.2 S(CH.sub.2).sub.2 F N(CH.sub.3)OH6205 CH.sub.2 S(CH.sub.2).sub.2 F NHOCH.sub.36206 CH.sub.2 S(CH.sub.2).sub.2 F NHOCH.sub.2CHCH.sub.26207 CH.sub.2 S(CH.sub.2).sub.2 F NHOCH.sub.2 CCH6208 CH.sub.2 S(CH.sub.2).sub.2 F NHOCH.sub.2 Ph6209 CH.sub.2 S(CH.sub.2).sub.2 F NHOCH.sub.2 CO.sub.2 CH.sub.36210 CH.sub.2 S(CH.sub.2).sub.2 F NHN(CH.sub.3).sub.26211 CH.sub.2 S(CH.sub.2).sub.2 F NH-2-pyridyl6212 CH.sub.2 S(CH.sub.2).sub.2 F NH-2-thiadiazoly6213 CH.sub.2 S (CH.sub.2).sub.2 F N.sub.36214 CH.sub.2 S(CH.sub.2).sub.2 F SCH.sub.36215 CH.sub.2 SO(CH.sub.2).sub.2 F SC.sub.2 H.sub.56216a (CH.sub.2).sub.2 SCH.sub.2 F OH cis6216b (CH.sub.2).sub.2 SCH.sub.2 F OH trans6217a (CH.sub.2).sub.2 SCH.sub.2 F OCH.sub.3 cis6217b (CH.sub.2).sub.2 SCH.sub.2 F OCH.sub.3 trans6218 (CH.sub.2).sub.2 SCH.sub.2 F OC.sub.2 H.sub.56219 (CH.sub.2).sub.2 SCH.sub.2 F O-i-C.sub.3 H.sub.76220 (CH.sub.2).sub.2 SCH.sub.2 F O(CH.sub.2).sub.2Cl6221 (CH.sub.2).sub.2 SCH.sub.2 F OCH.sub.2 SCH.sub.36222 (CH.sub.2).sub.2 SCH.sub.2 F OCH.sub.2 Ph6223 (CH.sub.2).sub.2 SCH.sub.2 F OPh6224 (CH.sub.2).sub.2 SCH.sub.2 F OCH.sub.2 CHCH.sub.26225 (CH.sub.2).sub.2 SCH.sub.2 F OCH.sub.2 CCH6226 (CH.sub.2).sub.2 SCH.sub.2 F OCH.sub.2 OC.sub.2 H.sub.56227 (CH.sub.2).sub.2 SCH.sub.2 F NH.sub.26228 (CH.sub.2).sub.2 SCH.sub.2 F NHCH.sub.36229 (CH.sub.2).sub.2 SCH.sub.2 F N(CH.sub.3)Ph6230 (CH.sub.2).sub.2 SCH.sub.2 F NHOH6231 (CH.sub.2).sub.2 SCH.sub.2 F N(CH.sub.3)OH6232 (CH.sub.2).sub.2 SCH.sub.2 F NHOCH.sub.36233 (CH.sub.2).sub.2 SCH.sub.2 F NHOCH.sub.2 CHCH.sub.26234 (CH.sub.2).sub.2 S CH.sub.2 F NHOCH.sub.2 CCH6235 (CH.sub.2).sub.2 SCH.sub.2 F NHOCH.sub.2 Ph6236 (CH.sub.2).sub.2 SCH.sub.2 F NHOCH.sub.2 CO.sub.2 CH.sub.36237 (CH.sub.2).sub.2 SCH.sub.2 F NHN(CH.sub.3).sub.26238 (CH.sub.2).sub.2 SCH.sub.2 F NH-2-pyridyl6239 (CH.sub.2).sub.2 SCH.sub.2 F NH-2-thiadiazoly6240 (CH.sub.2).sub.2 SCH.sub.2 F N.sub.36241 (CH.sub.2).sub.2 SCH.sub.2 F SCH.sub.36242 (CH.sub.2).sub.2 SCH.sub.2 F SC.sub.2 H.sub.56243 (CH.sub.2).sub.3 S F OH6244 (CH.sub.2).sub.3 S F OCH.sub.36245 (CH.sub.2).sub.3 S F OC.sub.2 H.sub.56246 (CH.sub.2).sub.3 S F O-i-C.sub.3 H.sub.76247 (CH.sub.2).sub.3 S F O(CH.sub.2).sub.2 Cl6248 (CH.sub.2).sub.3 S F OCH.sub.2 SCH.sub.36249 (CH.sub.2).sub.3 S F OCH.sub.2 Ph6250 (CH.sub.2).sub.3 S F OPh6251 (CH.sub.2).sub.3 S F OCH.sub.2 CHCH.sub.26252 (CH.sub.2).sub.3 S F OCH.sub.2 CCH6253 (CH.sub.2).sub.3 S F OCH.sub.2 OC.sub.2 H.sub.56254 (CH.sub.2).sub.3 S F NH.sub.26255 (CH.sub.2).sub.3 S F NHCH.sub.36256 (CH.sub.2).sub.3 S F N(CH.sub.3)Ph6257 (CH.sub.2).sub.3 S F NHOH6258 (CH.sub.2).sub.3 S F N(CH.sub.3)OH6259 (CH.sub.2).sub.3 S F NHOCH.sub.36260 (CH.sub.2).sub.3 S F NHOCH.sub.2 CHCH.sub.26261 (CH.sub.2).sub.3 S F NHOCH.sub.2 CCH6262 (CH.sub.2).sub.3 S F NHOCH.sub.2 Ph6263 (CH.sub.2).sub.3 S F NHOCH.sub.2 CO.sub.2 CH.sub.36264 (CH.sub.2).sub.3 S F NHN(CH.sub.3).sub.26265 (CH.sub.2).sub.3 S F NH-2-pyridyl6266 (CH.sub.2).sub.3 S F NH-2-thiadiazoly6267 (CH.sub.2).sub.3 S F N.sub.36268 (CH.sub.2).sub.3 S F SCH.sub.36269 (CH.sub.2).sub.3 S F SC.sub.2 H.sub.56270 CH.sub.2 NCH.sub.2 F OH6271 CH.sub.2 NHCH.sub.2 F OCH.sub.36272 CH.sub.2 NHCH.sub.2 F OC.sub.2 H.sub.56273 CH.sub.2 NHCH.sub.2 F O-i-C.sub.3 H.sub.76274 CH.sub.2 NHCH.sub.2 F O(CH.sub.2).sub.2 Cl6275 CH.sub.2 NHCH.sub.2 F OCH.sub.2 SCH.sub.36276 CH.sub.2 NHCH.sub.2 F OCH.sub.2 Ph6277 CH.sub.2 NHCH.sub.2 F OPh6278 CH.sub.2 NHCH.sub.2 F OCH.sub.2 CHCH.sub.26279 CH.sub.2 NHCH.sub.2 F OCH.sub.2 CCH6280 CH.sub.2 NHCH.sub.2 F OCH.sub.2 OC.sub.2 H.sub.56281 CH.sub.2 NHCH.sub.2 F NH.sub.26282 CH.sub.2 NHCH.sub.2 F NHCH.sub.36283 CH.sub.2 NHCH.sub.2 F N(CH.sub.3)Ph6284 CH.sub.2 NHCH.sub.2 F NHOH6285 CH.sub.2 NHCH.sub.2 F N(CH.sub.3)OH6286 CH.sub.2 NHCH.sub.2 F NHOCH.sub. 36287 CH.sub.2 NHCH.sub.2 F NHOCH.sub.2 CHCH.sub.26288 CH.sub.2 NHCH.sub.2 F NHOCH.sub.2CCH6289 CH.sub.2 NHCH.sub.2 F NHOCH.sub.2 Ph6290 CH.sub.2 NHCH.sub.2 F NHOCH.sub.2 CO.sub.2 CH.sub.36291 CH.sub.2 NHCH.sub.2 F NHN(CH.sub.3).sub.26292 CH.sub.2 NHCH.sub.2 F NH-2-pyridyl6293 CH.sub.2 NHCH.sub.2 F NH-2-thiadiazoly6294 CH.sub.2 NHCH.sub.2 F N.sub.36295 CH.sub.2 NHCH.sub.2 F SCH.sub.36296 CH.sub.2 NHCH.sub.2 F SC.sub.2 H.sub.56297 (CH.sub.2).sub.2 NH F OH6298 (CH.sub.2).sub.2 NH F OCH.sub.36299 (CH.sub.2).sub.2 NH F OC.sub.2 H.sub.56300 (CH.sub.2).sub.2 NH F O-i-C.sub.3 H.sub.76301 (CH.sub.2).sub.2 NH F O(CH.sub.2).sub.2 Cl6302 (CH.sub.2).sub.2 NH F OCH.sub.2 SCH.sub.36303 (CH.sub.2).sub.2 NH F OCH.sub.2 Ph6304 (CH.sub.2).sub.2 NH F OPh6305 (CH.sub.2).sub.2 NH F OCH.sub.2 CHCH.sub.26306 (CH.sub.2).sub.2 NH F OCH.sub.2 CCH6307 (CH.sub.2).sub.2 NH F OCH.sub.2 OC.sub.2 H.sub.56308 (CH.sub.2).sub.2 NH F NH.sub.26309 (CH.sub.2).sub.2 NH F NHCH.sub.36310 (CH.sub.2).sub.2 NH F N(CH.sub.3)Ph6311 (CH.sub.2).sub.2 NH F NHOH6312 (CH.sub.2).sub.2 NH F N(CH.sub.3)OH6313 (CH.sub.2).sub.2 NH F NHOCH.sub.36314 (CH.sub.2).sub.2 NH F NHOCH.sub.2 CHCH.sub.26315 (CH.sub.2).sub.2 NH F NHOCH.sub.2 CCH6316 (CH.sub.2).sub.2 NH F NHOCH.sub.2 Ph6317 (CH.sub.2).sub.2 NH F NHOCH.sub.2 CO.sub.2 CH.sub.36318 (CH.sub.2).sub.2 NH F NHN(CH.sub.3).sub.26319 (CH.sub.2).sub.2 NH F NH-2-pyridyl6320 (CH.sub.2).sub.2 NH F NH-2-thiadiazoly6321 (CH.sub.2).sub.2 NH F N.sub.36322 (CH.sub.2).sub.2 NH F SCH.sub.36323 (CH.sub.2).sub.2 NH F SC.sub.2 H.sub.56324 CH.sub.2 NH(CH.sub.2).sub.2 F OH6325 CH.sub.2 NH(CH.sub.2).sub.2 F OCH.sub.36326 CH.sub.2 NH(CH.sub.2).sub.2 F OC.sub.2 H.sub.56327 CH.sub.2 NH(CH.sub.2).sub.2 F O-i-C.sub.3 H.sub.76328 CH.sub.2 NH(CH.sub.2).sub.2 F O(CH.sub.2).sub.2 Cl6329 CH.sub.2 NH(CH.sub.2).sub.2 F OCH.sub.2 SCH.sub.36330 CH.sub.2 NH(CH.sub.2).sub.2 F OCH.sub.2 Ph6331 CH.sub.2 NH(CH.sub.2).sub.2 F OPh6332 CH.sub.2 NH(CH.sub.2).sub.2 F OCH.sub.2 CHCH.sub.26333 CH.sub.2 NH(CH.sub.2).sub.2 F OCH.sub.2 CCH6334 CH.sub.2 NH(CH.sub.2).sub.2 F OCH.sub.2 OC.sub.2 H.sub.56335 CH.sub.2 NH(CH.sub.2).sub.2 F NH.sub.26336 CH.sub.2 NH(CH.sub.2).sub.2 F NHCH.sub.36337 CH.sub.2 NH(CH.sub.2).sub.2 F N(CH.sub.3)Ph6338 CH.sub.2 NH(CH.sub.2).sub.2 F NHOH6339 CH.sub.2 NH(CH.sub.2).sub.2 F N(CH.sub.3)OH6340 CH.sub.2 NH(CH.sub.2).sub.2 F NHOCH.sub.36341 CH.sub.2 NH(CH.sub.2).sub.2 F NHOCH.sub.2 CHCH.sub.26342 CH.sub.2 NH(CH.sub.2).sub.2 F NHOCH.sub.2 CCH6343 CH.sub.2 NH(CH.sub.2).sub.2 F NHOCH.sub.2 Ph6344 CH.sub.2 NH(CH.sub.2).sub.2 F NHOCH.sub.2 CO.sub.2 CH.sub.36345 CH.sub.2 NH(CH.sub.2).sub.2 F NHN(CH.sub.3).sub.26346 CH.sub.2 NH(CH.sub.2).sub.2 F NH-2-pyridyl6347 CH.sub.2 NH(CH.sub.2).sub.2 F NH-2-thiadiazoly6348 CH.sub.2 NH(CH.sub.2).sub.2 F N.sub.36349 CH.sub.2 NH(CH.sub.2).sub.2 F SCH.sub.36350 CH.sub.2 NH(CH.sub.2).sub.2 F SC.sub.2 H.sub.56351 (CH.sub.2).sub.2 NHCH.sub.2 F OH6352 (CH.sub.2).sub.2 NHCH.sub.2 F OCH.sub.36353 (CH.sub.2).sub.2 NHCH.sub.2 F OC.sub.2 H.sub.56354 (CH.sub.2).sub.2 NHCH.sub.2 F O-i-C.sub.3 H.sub.76355 (CH.sub.2).sub.2 NHCH.sub.2 F O(CH.sub.2).sub.2 Cl6356 (CH.sub.2).sub.2 NHCH.sub.2 F OCH.sub.2 SCH.sub.36357 (CH.sub.2).sub.2 NHCH.sub.2 F OCH.sub.2 Ph6358 (CH.sub.2).sub.2 NHCH.sub.2 F OPh6359 (CH.sub.2).sub.2 NHCH.sub.2 F OCH.sub.2 CHCH.sub.26360 (CH.sub.2).sub.2 NH CH.sub.2 F OCH.sub.2 CCH6361 (CH.sub.2).sub.2 NHCH.sub.2 F OCH.sub.2 OC.sub.2 H.sub.56362 (CH.sub.2).sub.2 NHCH.sub.2 F NH.sub.26363 (CH.sub.2).sub.2 NHCH.sub.2 F NHCH.sub.36364 (CH.sub.2).sub.2 NHCH.sub.2 F N(CH.sub.3)Ph6365 (CH.sub.2).sub.2 NHCH.sub.2 F NHOH6366 (CH.sub.2).sub.2 NHCH.sub.2 F N(CH.sub.3)OH6367 (CH.sub.2).sub.2 NHCH.sub.2 F NHOCH.sub.36368 (CH.sub.2).sub.2 NHCH.sub.2 F NHOCH.sub.2 CHCH.sub.26369 (CH.sub.2).sub.2 NHCH.sub.2 F NHOCH.sub.2 CCH6370 (CH.sub.2).sub.2 NHCH.sub.2 F NHOCH.sub.2 Ph6371 (CH.sub.2).sub.2 NHCH.sub.2 F NHOCH.sub.2 CO.sub.2 CH.sub.36372 (CH.sub.2).sub.2 NHCH.sub.2 F NHN(CH.sub.3).sub.26373 (CH.sub.2).sub.2 NHCH.sub.2 F NH-2-pyridyl6374 (CH.sub.2).sub.2 NHCH.sub.2 F NH-2-thiadiazoly6375 (CH.sub.2).sub.2 NHCH.sub.2 F N.sub.36376 (CH.sub.2).sub.2 NHCH.sub.2 F SCH.sub.36377 (CH.sub.2).sub.2 NHCH.sub.2 F SC.sub.2 H.sub.56378 (CH.sub.2).sub.3 NH F OH6379 (CH.sub.2).sub.3 NH F OCH.sub.36380 (CH.sub.2).sub.3 NH F OC.sub.2 H.sub.56381 (CH.sub.2).sub.3 NH F O-i-C.sub.3 H.sub.76382 (CH.sub.2).sub.3 NH F O(CH.sub.2).sub.2 Cl6383 (CH.sub.2).sub.3 NH F OCH.sub.2 SCH.sub.36384 (CH.sub.2).sub.3 NH F OCH.sub.2 Ph6385 (CH.sub.2).sub.3 NH F OPh6386 (CH.sub.2).sub.3 NH F OCH.sub.2 CHCH.sub.26387 (CH.sub.2).sub.3 NH F OCH.sub.2 CCH6388 (CH.sub.2).sub.3 NH F OCH.sub.2 OC.sub.2 H.sub.56389 (CH.sub.2).sub.3 NH F NH.sub.26390 (CH.sub.2).sub.3 NH F NHCH.sub.36391 (CH.sub.2).sub.3 NH F N(CH.sub.3)Ph6392 (CH.sub.2).sub.3 NH F NHOH6393 (CH.sub.2).sub.3 NH F N(CH.sub.3)OH6394 (CH.sub.2).sub.3 NH F NHOCH.sub.36395 (CH.sub.2).sub.3 NH F NHOCH.sub.2 CHCH.sub.26396 (CH.sub.2).sub.3 NH F NHOCH.sub.2 CCH6397 (CH.sub.2).sub.3 NH F NHOCH.sub. 2 Ph6398 (CH.sub.2).sub.3 NH F NHOCH.sub.2 CO.sub.2 CH.sub.36399 (CH.sub.2).sub.3 NH F NHN(CH.sub.3).sub.26400 (CH.sub.2).sub.3 NH F NH-2-pyridyl6401 (CH.sub.2).sub.3 NH F NH-2-thiadiazoly6402 (CH.sub.2).sub.3 NH F N.sub.36403 (CH.sub.2).sub.3 NH F SCH.sub.36404 (CH.sub.2).sub.3 NH F SC.sub.2 H.sub.56405 CH.sub.2 N(CO.sub.2 CH.sub.3)(CH.sub.2).sub.2 F OH6406 CH.sub.2 N(CO.sub.2 CH.sub.3)(CH.sub.2).sub.2 F OCH.sub.36407 CH.sub.2 N(CO.sub.2 CH.sub.3)(CH.sub.2).sub.2 F OC.sub.2 H.sub.56408 CH.sub.2 N(CO.sub.2 CH.sub.3)(CH.sub.2).sub.2 F O-i-C.sub.3 H.sub.76409 CH.sub.2 N(CO.sub.2 CH.sub.3)(CH.sub.2).sub.2 F O(CH.sub.2).sub. 2 Cl6410 CH.sub.2 N(CO.sub.2 CH.sub.3)(CH.sub.2).sub.2 F OCH.sub.2 SCH.sub.36411 CH.sub.2 N(CO.sub.2 CH.sub.3)(CH.sub.2).sub.2 F OCH.sub.2 Ph6412 CH.sub.2 N(CO.sub.2 CH.sub.3)(CH.sub.2).sub.2 F OPh6413 CH.sub.2 N(CO.sub.2 CH.sub.3)(CH.sub.2).sub.2 F OCH.sub.2 CHCH.sub.26414 CH.sub.2 N(CO.sub.2 CH.sub.3)(CH.sub.2).sub.2 F OCH.sub.2 CCH6415 CH.sub.2 N(CO.sub.2 CH.sub.3)(CH.sub.2).sub.2 F OCH.sub.2 OC.sub.2 H.sub.56416 CH.sub.2 N(CO.sub.2 CH.sub.3)(CH.sub.2).sub.2 F NH.sub.26417 CH.sub.2 N(CO.sub.2 CH.sub.3)(CH.sub.2).sub.2 F NHCH.sub.36418 CH.sub.2 N(CO.sub.2 CH.sub.3)(CH.sub.2).sub.2 F N(CH.sub.3)Ph6419 CH.sub.2 N(CO.sub.2 CH.sub.3)(CH.sub.2).sub.2 F NHOH6420 CH.sub.2 N(CO.sub.2 CH.sub.3)(CH.sub.2).sub.2 F N(CH.sub.3)OH6421 CH.sub.2 N(CO.sub.2 CH.sub.3)(CH.sub.2).sub.2 F NHOCH.sub.36422 CH.sub.2 N(CO.sub.2 CH.sub.3)(CH.sub.2).sub.2 F NHOCH.sub.2 CHCH.sub.26423 CH.sub.2 N(CO.sub.2 CH.sub.3)(CH.sub.2).sub.2 F NHOCH.sub.2 CCH6424 CH.sub.2 N(CO.sub.2 CH.sub.3)(CH.sub.2).sub.2 F NHOCH.sub.2 Ph6425 CH.sub.2 N(CO.sub.2 CH.sub.3)(CH.sub.2).sub.2 F NHOCH.sub.2 CO.sub.2 CH.sub.36426 CH.sub.2 N(CO.sub.2 CH.sub.3)(CH.sub.2).sub.2 F NHN(CH.sub.3).sub.26427 CH.sub.2 N(CO.sub.2 CH.sub.3)(CH.sub.2).sub.2 F NH-2-pyridyl6428 CH.sub.2 N(CO.sub.2 CH.sub.3)(CH.sub.2).sub.2 F NH-2-thiadiazoly6429 CH.sub.2 N(CO.sub.2 CH.sub.3)(CH.sub.2).sub.2 F N.sub.36430 CH.sub.2 N(CO.sub.2 CH.sub.3)(CH.sub.2).sub.2 F SCH.sub.36431 CH.sub.2 N(CO.sub.2 CH.sub.3)(CH.sub.2).sub.2 F SC.sub.2 H.sub.56432 CH.sub.2 N(COCH.sub.3)(CH.sub.2).sub.2 F OH6433 CH.sub.2 N(COCH.sub.3)(CH.sub.2).sub.2 F OCH.sub.36434 CH.sub.2 N(COCH.sub.3)(CH.sub.2).sub.2 F OC.sub.2 H.sub.56435 CH.sub.2 N(COCH.sub.3)(CH.sub.2).sub.2 F O-i-C.sub.3 H.sub.76436 CH.sub.2 N(COCH.sub.3)(CH.sub.2).sub.2 F O(CH.sub.2).sub.2 Cl6437 CH.sub.2 N(COCH.sub.3)(CH.sub.2).sub.2 F OCH.sub.2 SCH.sub.36438 CH.sub.2 N(COCH.sub.3)(CH.sub.2 ).sub.2 F OCH.sub.2 Ph6439 CH.sub.2 N(COCH.sub.3)(CH.sub.2).sub.2 F OPh6440 CH.sub.2 N(COCH.sub.3)(CH.sub.2).sub.2 F OCH.sub.2 CHCH.sub.26441 CH.sub.2 N(COCH.sub.3)(CH.sub.2).sub.2 F OCH.sub.2 CCH6442 CH.sub.2 N(COCH.sub.3)(CH.sub.2).sub.2 F OCH.sub.2 OC.sub.2 H.sub.56443 CH.sub.2 N(COCH.sub.3)(CH.sub.2).sub.2 F NH.sub.26444 CH.sub.2 N(COCH.sub.3)(CH.sub.2).sub.2 F NHCH.sub.36445 CH.sub.2 N(COCH.sub.3)(CH.sub.2).sub.2 F N(CH.sub.3)Ph6446 CH.sub.2 N(COCH.sub.3)(CH.sub.2).sub.2 F NHOH6447 CH.sub.2 N(COCH.sub.3)(CH.sub.2).sub.2 F N(CH.sub.3)OH6448 CH.sub.2 N(COCH.sub.3)(CH.sub.2 ).sub.2 F NHOCH.sub.36449 CH.sub.2 N(COCH.sub.3)(CH.sub.2).sub.2 F NHOCH.sub.2 CHCH.sub.26450 CH.sub.2 N(COCH.sub.3)(CH.sub.2).sub.2 F NHOCH.sub.2 CCH6451 CH.sub.2 N(COCH.sub.3)(CH.sub.2).sub.2 F NHOCH.sub.2 Ph6452 CH.sub.2 N(COCH.sub.3)(CH.sub.2).sub.2 F NHOCH.sub.2 CO.sub.2 CH.sub.36453 CH.sub.2 N(COCH.sub.3)(CH.sub.2).sub.2 F NHN(CH.sub.3).sub.26454 CH.sub.2 N(COCH.sub.3)(CH.sub.2).sub.2 F NH-2-pyridyl6455 CH.sub.2 N(COCH.sub.3)(CH.sub.2).sub.2 F NH-2-thiadiazoly6456 CH.sub.2 N(COCH.sub.3)(CH.sub.2).sub.2 F N.sub.36457 CH.sub.2 N(COCH.sub.3)(CH.sub.2).sub.2 F SCH.sub.36458 CH.sub.2 N(COCH.sub.3)(CH.sub.2).sub.2 F SC.sub.2 H.sub.56459a (CH.sub.2).sub.2 N(CO.sub.2 CH.sub.3)CH.sub.2 F OH cis6459b (CH.sub.2).sub.2 N(CO.sub.2 CH.sub.3)CH.sub.2 F OH trans6460a (CH.sub.2).sub.2 N(CO.sub.2 CH.sub.3)CH.sub.2 F OCH.sub.3 cis6460b (CH.sub.2).sub.2 N(CO.sub.2 CH.sub.3)CH.sub.2 F OCH.sub.3 trans6461 (CH.sub.2).sub.2 N(CO.sub.2 CH.sub.3)CH.sub.2 F OC.sub.2 H.sub.56462 (CH.sub.2).sub.2 N(CO.sub.2 CH.sub.3)CH.sub.2 F O-i-C.sub.3 H.sub.76463 (CH.sub.2).sub.2 N(CO.sub.2 CH.sub.3)CH.sub.2 F O(CH.sub.2).sub.2 Cl6464 (CH.sub.2).sub.2 N(CO.sub.2 CH.sub.3)CH.sub.2 F OCH.sub.2 SCH.sub.36465 (CH.sub.2).sub.2 N(CO.sub.2 CH.sub.3)CH.sub.2 F OCH.sub.2 Ph6466 (CH.sub.2).sub.2 N(CO.sub.2 CH.sub.3)CH.sub.2 F OPh6467 (CH.sub.2).sub.2 N(CO.sub.2 CH.sub.3)CH.sub.2 F OCH.sub.2 CHCH.sub.26468 (CH.sub.2).sub.2 N(CO.sub.2 CH.sub.3)CH.sub.2 F OCH.sub.2 CCH6469 (CH.sub.2).sub.2 N(CO.sub.2 CH.sub.3)CH.sub.2 F OCH.sub.2 OC.sub.2 H.sub.56470 (CH.sub.2).sub.2 N(CO.sub.2 CH.sub.3)CH.sub.2 F NH.sub.26471 (CH.sub.2).sub.2 N(CO.sub.2 CH.sub.3)CH.sub.2 F NHCH.sub.36472 (CH.sub.2).sub.2 N(CO.sub.2 CH.sub.3)CH.sub.2 F N(CH.sub.3)Ph6473 (CH.sub.2).sub.2 N(CO.sub.2 CH.sub.3)CH.sub.2 F NHOH6474 (CH.sub.2).sub.2 N(CO.sub.2 CH.sub.3)CH.sub.2 F N(CH.sub.3)OH6475 (CH.sub.2).sub.2 N(CO.sub.2 CH.sub.3)CH.sub.2 F NHOCH.sub.36476 (CH.sub.2).sub.2 N(CO.sub.2 CH.sub.3)CH.sub.2 F NHOCH.sub.2 CHCH.sub.26477 (CH.sub.2).sub.2 N(CO.sub.2 CH.sub.3)CH.sub.2 F NHOCH.sub.2 CCH6478 (CH.sub.2).sub.2 N(CO.sub.2 CH.sub.3)CH.sub.2 F NHOCH.sub.2 Ph6479 (CH.sub.2).sub.2 N(CO.sub.2 CH.sub.3)CH.sub.2 F NHOCH.sub.2 CO.sub.2 CH.sub.36480 (CH.sub.2).sub.2 N(CO.sub.2 CH.sub.3)CH.sub.2 F NHN(CH.sub.3).sub.26481 (CH.sub.2).sub.2 N(CO.sub.2 CH.sub.3)CH.sub.2 F NH-2-pyridyl6482 (CH.sub.2).sub.2 N(CO.sub.2 CH.sub.3)CH.sub.2 F NH-2-thiadiazoly6483 (CH.sub.2).sub.2 N(CO.sub.2 CH.sub.3)CH.sub.2 F N.sub.36484 (CH.sub.2).sub.2 N(CO.sub.2 CH.sub.3)CH.sub.2 F S CH.sub.36485 (CH.sub.2).sub.2 N(CO.sub.2 CH.sub.3)CH.sub.2 F SC.sub.2 H.sub.56486 (CH.sub.2).sub.2 N(COCH.sub.3)CH.sub.2 F OH6487 (CH.sub.2).sub.2 N(COCH.sub.3)CH.sub.2 F OCH.sub.36488 (CH.sub.2).sub.2 N(COCH.sub.3)CH.sub.2 F OC.sub.2 H.sub.56489 (CH.sub.2).sub.2 N(COCH.sub.3)CH.sub.2 F O-i-C.sub.3 H.sub.76490 (CH.sub.2).sub.2 N(COCH.sub.3)CH.sub.2 F O(CH.sub.2).sub.2 Cl6491 (CH.sub.2).sub.2 N(COCH.sub.3)CH.sub.2 F OCH.sub.2 SCH.sub.36492 (CH.sub.2).sub.2 N(COCH.sub.3)CH.sub.2 F OCH.sub.2 Ph6493 (CH.sub.2).sub.2 N(COCH.sub.3)CH.sub.2 F OPh6494 (CH.sub.2).sub.2 N(COCH.sub.3)CH.sub.2 F OCH.sub.2 CHCH.sub.26495 (CH.sub.2).sub.2 N(COCH.sub.3)CH.sub.2 F OCH.sub.2 CCH6496 (CH.sub.2).sub.2 N(COCH.sub.3)CH.sub.2 F OCH.sub.2 OC.sub.2 H.sub.56497 (CH.sub.2).sub.2 N(COCH.sub.3)CH.sub.2 F NH.sub.26498 (CH.sub.2).sub.2 N(COCH.sub.3)CH.sub.2 F NHCH.sub.36499 (CH.sub.2).sub.2 N(COCH.sub.3)CH.sub.2 F N(CH.sub.3)Ph6500 (CH.sub.2).sub.2 N(COCH.sub.3)CH.sub.2 F NHOH6501 (CH.sub.2).sub.2 N(COCH.sub.3)CH.sub.2 F N(CH.sub.3)OH6502 (CH.sub.2).sub.2 N(COCH.sub.3)CH.sub.2 F NHOCH.sub.36503 (CH.sub.2).sub.2 N(COCH.sub.3)CH.sub.2 F NHOCH.sub.2 CHCH.sub.26504 (CH.sub.2).sub.2 N(COCH.sub.3)CH.sub.2 F NHOCH.sub.2 CCH6505 (CH.sub.2).sub.2 N(COCH.sub.3)CH.sub.2 F NHOCH.sub.2 Ph6506 (CH.sub.2).sub.2 N(COCH.sub.3)CH.sub.2 F NHOCH.sub.2 CO.sub.2 CH.sub.36507 (CH.sub.2).sub.2 N(COCH.sub.3)CH.sub.2 F NHN(CH.sub.3).sub.26508 (CH.sub.2).sub.2 N(COCH.sub.3)CH.sub.2 F NH-2-pyridyl6509 (CH.sub.2).sub.2 N(COCH.sub.3)CH.sub.2 F NH-2-thiadiazoly6510 (CH.sub.2).sub.2 N(COCH.sub.3)CH.sub.2 F N.sub.36511 (CH.sub.2).sub.2 N(COCH.sub.3)CH.sub.2 F SCH.sub.36512 (CH.sub.2).sub.2 N(COCH.sub.3)CH.sub.2 F SC.sub.2 H.sub.56513 (CH.sub.2).sub.3 N(CO.sub.2 CH.sub.3) F OH6514 (CH.sub.2).sub.3 N(CO.sub.2 CH.sub.3) F OCH.sub.36515 (CH.sub.2).sub.3 N(CO.sub.2 CH.sub.3) F OC.sub. 2 H.sub.56516 (CH.sub.2).sub.3 N(CO.sub.2 CH.sub.3) F O-i-C.sub.3 H.sub.76517 (CH.sub.2).sub.3 N(CO.sub.2 CH.sub.3) F O(CH.sub.2).sub.2 Cl6518 (CH.sub.2).sub.3 N(CO.sub.2 CH.sub.3) F OCH.sub.2 SCH.sub.36519 (CH.sub.2).sub.3 N(CO.sub.2 CH.sub.3) F OCH.sub.2 Ph6520 (CH.sub.2).sub.3 N(CO.sub.2 CH.sub.3) F OPh6521 (CH.sub.2).sub.3 N(CO.sub.2 CH.sub.3) F OCH.sub.2 CHCH.sub.26522 (CH.sub.2).sub.3 N(CO.sub.2 CH.sub.3) F OCH.sub.2 CCH6523 (CH.sub.2).sub.3 N(CO.sub.2 CH.sub.3) F OCH.sub.2 OC.sub.2 H.sub.56524 (CH.sub.2).sub.3 N(CO.sub.2 CH.sub.3) F NH.sub.26525 (CH.sub.2).sub.3 N(CO.sub.2 CH.sub.3) F NHCH.sub.36526 (CH.sub.2).sub. 3 N(CO.sub.2 CH.sub.3) F N(CH.sub.3)Ph6527 (CH.sub.2).sub.3 N(CO.sub.2 CH.sub.3) F NHOH6528 (CH.sub.2).sub.3 N(CO.sub.2 CH.sub.3) F N(CH.sub.3)OH6529 (CH.sub.2).sub.3 N(CO.sub.2 CH.sub.3) F NHOCH.sub.36530 (CH.sub.2).sub.3 N(CO.sub.2 CH.sub.3) F NHOCH.sub.2 CHCH.sub.26531 (CH.sub.2).sub.3 N(CO.sub.2 CH.sub.3) F NHOCH.sub.2 CCH6532 (CH.sub.2).sub.3 N(CO.sub.2 CH.sub.3) F NHOCH.sub.2 Ph6533 (CH.sub.2).sub.3 N(CO.sub.2 CH.sub.3) F NHOCH.sub.2 CO.sub.2 CH.sub.36534 (CH.sub.2).sub.3 N(CO.sub.2 CH.sub.3) F NHN(CH.sub.3).sub.26535 (CH.sub.2).sub.3 N(CO.sub.2 CH.sub.3) F NH-2-pyridyl6536 (CH.sub.2).sub.3 N(CO.sub.2 CH.sub.3) F NH-2-thiadiazoly6537 (CH.sub.2).sub.3 N(CO.sub.2 CH.sub.3) F N.sub.36538 (CH.sub.2).sub.3 N(CO.sub.2 CH.sub.3) F SCH.sub.36539 (CH.sub.2).sub.3 N(CO.sub.2 CH.sub.3) F SC.sub.2 H.sub.56540 (CH.sub.2).sub.3 N(COCH.sub.3) F OH6541 (CH.sub.2).sub.3 N(COCH.sub.3) F OCH.sub.36542 (CH.sub.2).sub.3 N(COCH.sub.3) F OC.sub.2 H.sub.56543 (CH.sub.2).sub.3 N(COCH.sub.3) F O-i-C.sub.3 H.sub.76544 (CH.sub.2).sub.3 N(COCH.sub.3) F O(CH.sub.2).sub.2 Cl6545 (CH.sub.2).sub.3 N(COCH.sub.3) F OCH.sub.2 SCH.sub.36546 (CH.sub.2).sub.3 N(COCH.sub.3) F OCH.sub.2 Ph6547 (CH.sub.2).sub.3 N(COCH.sub.3) F OPh6548 (CH.sub.2).sub.3 N(COCH.sub.3) F OCH.sub.2 CHCH.sub. 26549 (CH.sub.2).sub.3 N(COCH.sub.3) F OCH.sub.2 CCH6550 (CH.sub.2).sub.3 N(COCH.sub.3) F OCH.sub.2 OC.sub.2 H.sub.56551 (CH.sub.2).sub.3 N(COCH.sub.3) F NH.sub.26552 (CH.sub.2).sub.3 N(COCH.sub.3) F NHCH.sub.36553 (CH.sub.2).sub.3 N(COCH.sub.3) F N(CH.sub.3)Ph6554 (CH.sub.2).sub.3 N(COCH.sub.3) F NHOH6555 (CH.sub.2).sub.3 N(COCH.sub.3) F N(CH.sub.3)OH6556 (CH.sub.2).sub.3 N(COCH.sub.3) F NHOCH.sub.36557 (CH.sub.2).sub.3 N(COCH.sub.3) F NHOCH.sub.2 CHCH.sub.26558 (CH.sub.2).sub.3 N(COCH.sub.3) F NHOCH.sub.2 CCH6559 (CH.sub.2).sub.3 N(COCH.sub.3) F NHOCH.sub.2 Ph6560 (CH.sub.2).sub.3 N(COCH.sub.3) F NHOCH.sub.2 CO.sub.2 CH.sub.36561 (CH.sub.2).sub.3 N(COCH.sub.3) F NHN(CH.sub.3).sub.26562 (CH.sub.2).sub.3 N(COCH.sub.3) F NH-2-pyridyl6563 (CH.sub.2).sub.3 N(COCH.sub.3) F NH-2-thiadiazoly6564 (CH.sub.2).sub.3 N(COCH.sub.3) F N.sub.36565 (CH.sub.2).sub.3 N(COCH.sub.3) F SCH.sub.36566 (CH.sub.2).sub.3 N(COCH.sub.3) F SC.sub.2 H.sub.5__________________________________________________________________________
TABLE 7__________________________________________________________________________ ##STR27##CompoundNo. R.sup.5 R.sup.3 R.sup.4 X W Y Remarks__________________________________________________________________________7001 CH(CH.sub.2).sub.3 F S H7002 CH(CH.sub.2).sub.3 F S OH7003 CH(CH.sub.2).sub.3 F S OCH.sub.37004 CH(CH.sub.2).sub.3 F S OC.sub.2 H.sub.57005 CH(CH.sub.2).sub.3 F S O-n-C.sub.3 H.sub.77006 CH(CH.sub.2).sub.3 F S O-i-C.sub.3 H.sub.77007 CH(CH.sub.2).sub.3 F S O-n-C.sub.4 H.sub.97008 CH(CH.sub.2).sub.3 F S O-i-C.sub.4 H.sub. 97009 CH(CH.sub.2).sub.3 F S O-s-C.sub.4 H.sub.97010 CH(CH.sub.2).sub.3 F S O-t-C.sub.4 H.sub.97011 CH(CH.sub.2).sub.3 F S O(CH.sub.2).sub.2Cl7012 CH(CH.sub.2).sub.3 F S OCH.sub.2SCH.sub.37013 CH(CH.sub.2).sub.3 F S OCH.sub.2Ph7014 CH(CH.sub.2).sub.3 F S OPh7015 CH(CH.sub.2).sub.3 F S OCH.sub.2CHCH.sub.27016 CH(CH.sub.2).sub.3 F S OCH.sub.2CCH7017 CH(CH.sub.2).sub.3 F S OCH.sub.2OC.sub.2 H.sub.57018 CH.sub.3 (CH.sub.2).sub.4 F O OH7019 CH.sub.3 (CH.sub.2).sub.4 F O OCH.sub.37020 CH.sub.3 (CH.sub.2).sub.4 F O OC.sub.2 H.sub.57021 CH.sub.3 CH.sub. 3 CH.sub.3 F O OH7022 CH.sub.3 CH.sub.3 CH.sub.3 F O OCH.sub.37023 CH.sub.3 CH.sub.3 CH.sub.3 F O OC.sub.2 H.sub.57024 CHCH.sub.3 CH.sub.3 F O OH7025 CHCH.sub.3 CH.sub.3 F O OCH.sub.37026 CHCH.sub.3 CH.sub.3 F O OCH.sub.3__________________________________________________________________________
TABLE 8__________________________________________________________________________Compound .sup.1 H-NMR(.delta. ppm, CDCl.sub.3)No. and/or Physical data__________________________________________________________________________1002a mp 77-79.degree. C.1002a1 [.alpha.].sub.D.sup.30 =+18.5.degree. (C=0.029, iPrOH) (60% enantiomeric excess)1002a2 [.alpha.].sub.D.sup.30 =-14.2.degree. (c=0.049, iPrOH) (70% enantiomeric excess)1002b mp 122-124.degree. C.1002b1 [.alpha.].sub.D.sup.30 =+36.6.degree. (c=0.071, iPrOH) (99% enantiomeric excess)1002b2 [.alpha.].sub.D.sup.30 =-38.6.degree. (c=0.083, iPrOH) (87% enantiomeric excess)1003a 1.7-2.73(6H, m), 3.55(3H, s), 3.88(6H, s), 5.23-5.57(1H, m), 5.63(1H, s)1003b 1.53-2.77(6H, m), 3.71(3H, s), 3.87(6H, s), 5.3-5.76(1H, m), 5.63(1H, s)1004b 1.22(3H, t, J=7Hz), 1.53-2.69(6H, m), 3.88(6H, s), 4.17(2H, q, J=7Hz), 5.27-5.90(1H, m), 5.63(1H, s) mp 39.4-42.0.degree. C.1006a 1.08(3H, d, J=6Hz), 1.17(3H, d, J=6Hz), 1.74-2.74(6H, m), 3.91(6H, s), 4.92(1H, sep, J=6Hz), 5.66(1H, s), 5.27-5.86(1H, m)1006b 1.16(3H, d, J=6.2Hz), 1.26(3H, d, J=6.2Hz), 1.51-2.68(6H, m), 3.89(6H, s), 5.03(1H, sep), 5.66(1H, s), 5.31-5.95(1H, m)1007b 0.67-2.67(13H, m), 3.90(6H, s), 4.12(2H, t, J=6Hz), 5.33-5.92(1H, m), 5.66((1H, s)1009b 0.67-1.33(6H, m), 1.43-2.57(8H, m), 3.90(6H, s), 4.67-5.13(1H, m), 5.33-5.93(1H.m), 5.67(1H, s)1010a 1.37(9H, s), 1.67-2.67(6H, m), 3.92(6H, s), 5.67(1H, s), 5.23-5.82(1H, m) mp 77.0-79.9.degree. C.1010b 1.43(9H, s), 1.53-2.58(6H, m), 3.89(6H, s), 5.38-5.93(1H, m), 5.66(1H, s)1011a 1.70-2.77(6H, m), 3.60(2H, t, J=6Hz), 3.90(6H, s), 4.25(2H, t, J=6Hz), 5.69(1H, s), 5.30-5.87(1H, m)1011b 1.41-2.74(6H, m), 3.63(2H, t, J=6Hz), 3.87(6H, s), 4.37(2H, t, J=6Hz), 5.64(1H, s), 5.26-6.01(1H, m)1012a 2.14(3H, s), 1.73-2.73(6H, m), 3.88(6H, s), 5.02(2H, s)5.63(1H, s) 5.27-5.79(1H, m)1012b 2.17(3H, s), 1.53-2.70(6H, m), 3.89(6H, s), 5.17(2H, s), 5.66(1H, s) 5.32-5.90(1H, m)1013a 1.60-2.67(6H, m), 3.85(6H, s), 4.91(1H, s), 5.00(1H, s), 5.33-5.83 (1H, m), 5.62(1H, s), 7.24(5H, s)1013b 1.64-2.67(6H, m), 3.69(6H, s), 5.16(2H, s)5.62(1H, s), 5.34-5.92 (1H, m), 7.07-7.42(5H, m)1023a 1.69-2.79(6H, m), 3.92(6H, s), 5.69(1H, s), 5.42-5.97(1H, m), 6.64-7.45(5H, m)1023b 1.60-2.82(6H, m), 3.81(6H, s), 5.37-6.03(1H, m), 5.66(1H, s), 6.83-7.50(5H, m) mp.53.0-55.5.degree. C.1024a 1.67-2.77(6H, m), 3.93(6H, s), 5.72(1H, s), 5.43-6.03(1H, m), 6.87-7.53(4H, m)1024b 1.70-2.91(6H, m), 3.89(6H, s), 5.46-6.13(1H, m), 5.70(1H, s), 6.93-7.50(5H, m)1033a 1.70-2.67(6H, m), 3.89(6H, s), 4.33-4.55(2H, m), 4.97-5.41(2H, m), 5.67(1H, s), 5.43-6.03(2H, m)1033b 1.83-2.70(6H, m), 3.88(6H, s), 4.53-4.73(2H, m), 5.00-5.42(2H, m), 5.61(1H, s), 5.50-6.10(2H, m)1034a 2.35(1H, t, J=2.4Hz), 1.53-2.77(6H, m), 3.93(6H, s), 4.52(2H, d, J=2.4Hz), 5.64(1H, s), 5.30-5.80(1H, m)1034b 1.64-2.57(6H, m), 2.43(1H, t, J=2.4Hz), 3.88(6H, s), 4.72(2H, d, J=2.4Hz), 5.30-5.87(1H, m), 5.64(1H, s)1038b white powder1039b white powder1040b white powder1041b white powder1042b 1.40-2.67(6H, m), 1.70(3H, s), 1.77(3H, s), 3.91(6H, s), 5.37-5.97(1H, m), 5.67(1H, s)1043b 1.37-2.64(6H, m), 1.70(3H, s), 3.89(6H, s), 4.54(2H, s), 4.90(2H, bs) 5.30-5.95(1H, m), 5.63(1H, s)1069a 1.67-2.67(6H, m), 3.89(6H, s), 5.57(1H, s), 5.40-5.90(1H, m), 7.17-7.77(5H, m), 8.11(1H, s) mp 114.0-115.5.degree. C.1069b 1.47-2.80(6H, m), 3.87(6H, s), 5.62(1H, s), 5.34-6.07(1H, m), 7.14-7.80(5H, m), 8.26(1H, s)1075a 1.26(3H, t, J=7Hz), 2.00(3H, s), 1.66-2.53(6H, m), 3.88(6H, s), 4.11(2H, q, J=7Hz), 5.62(1H, s), 5.29-5.79(1H, m)1076b 1.57-2.60(6H, m), 2.82(4H, s), 3.86(6H, s), 5.67(1H, s), 5.43-6.03(1H, m)1081 0.93 and 1.02(3H, d, J=3.6Hz and J=2Hz), 1.02-2.63(5H, m), 3.71 (6H, s), 4.78-5.62(1H, m), 5.51(1H, s)1082 1.06-1.39(6H, m), 1.43-2.9(5H, m), 3.9(6H, s), 3.87-4.47(2H, m) 4.92-5.77(1H, m), 5.65(1H, s)1180a mp 179-181.degree. C.1180a1 [.alpha.].sub.D.sup.30 =+71.6.degree. (c=0.046, iPrOH) (96% enantiomeric excess)1180a2 [.alpha.].sub.D.sup.30 =-63.5.degree. (c=0.060, iPrOH) (86% enantiomeric excess)1180b mp 157.5-160.degree. C.1180b1 [.alpha.].sub.D.sup.30 =+5.0.degree. (c=0.092, iPrOH) (100% enantiomeric excess)1180b2 [.alpha.].sub.D.sup.30 =-5.0.degree. (c=0.10, iPrOH) (100% enantiomeric excess)1181a 1.0-2.67(8H, m), 3.63(3H, s), 3.88(6H, s), 5.43-5.77(1H, m), 5.77(1H, s)1181b 1.0-2.5(8H, m), 3.67(3H, s), 3.88(6H, s), 5.42-5.73(1H, m), 5.63 (1H, s)1182a 1.17(3H, t, J=7Hz), 1.30-2.30(8H, m), 3.90(6H, s), 4.10(2H, q, J=7Hz), 5.22-5.70(1H, m), 5.65(1H, s)1182b 1.17(3H, t, J=7Hz), 1.33-2.42(8H, m), 3.90(6H, s), 4.15(2H, q, J=7Hz), 5.02-5.42(1H, m), 5.63(1H, s) mp 107.5-110.0.degree. C.1183b 0.85(3H, t, J=6.4Hz), 1.19-2.38(11H, m), 3.89(6H, s), 4.05(2H, t, J=6.4Hz), 5.04-5.75(1H, m), 5.63(1H, s) mp 69.6-71.3.degree. C.1184a 1.12(3H, d, J=6Hz), 1.15(3H, d, J=6Hz), 1.37-2.27(8H, m), 3.87(6H, s), 4.95(1H, sep, J=6Hz), 5.50-5.80(1H, m), 5.83(1H, s)1184b 1.12(3H, d, J=6Hz), 1.18(3H, d, J=6Hz), 1.37-2.37(8H, m), 3.88(6H, s), 5.0(1H, sep, J=6Hz), 5.07-5.40(1H, m), 5.63(1H, s)1185b 0.60-2.40(15H, m), 3.93(6H, s), 4.10(2H, t, J=6Hz), 5.06-5.83(1H, m), 5.66(1H, s)1186b 0.85(6H, d, J=6Hz), 1.20-2.47(9H, m), 3.89(1H, d, J=6Hz), 3.90(1H, d, J=6Hz), 3.90(6H, s), 5.03-5.80(1H, m), 5.63(1H, s) mp 56.3-57.0.degree. C.1187b 0.70-1, 25(6H, m), 1.36-2.36(10H, m), 3.89(6H, s), 4.70-5.76(2H, m), 5.66(1H, s)1188b 1.33(9H, s), 1.40-2.33(8H, m), 3.87(6H, s), 5.00-5.35(1H, m), 5.63(1H, s) mp 143.5-146.5.degree. C.1189a 1.33-2.30(8H, m), 3.60(2H, t, J=6Hz), 3.90(6H, s), 4.30(2H, t, J=6Hz), 5.23-5.70(1H, m), 5.67(1H, s)1189b 1.07-2.57(8H, m), 3.47-3.80(2H, m), 3.88(6H, s), 4.23-4.53(2H, m), 5.00-5.53(1H, m), 5.65(1H, s)1190a 1.23-2.33(8H, m), 2.17(3H, s), 3.90(6H, s), 5.10(1H, s), 5.17(1H, s) 5.32-5.63(1H, m), 5.67(1H, s)1190b 1.00-2.33(8H, m), 2.13(3H, s), 3.90(6H, s), 5.17(2H, s), 5.27-5.53 (1H, m), 5.67(1H, s)1191a 1.10-2.38(8H, m), 3.85(6H, s), 4.93(1H, d, J=12Hz), 5.17(1H, d, J=12Hz) 5.30-5.72(1H, m), 5.62(1H, s), 7.20(5H, s)1191b 1.10-2.43(8H, m), 3.83(6H, s), 5.05(1H, d, J=12Hz), 5.15(1H, d, J=12Hz), 5.23-5.80(1H, m), 5.62(1H, s), 7.18(5H, s)1201a 1.17-3.07(8H, m), 3.90(6H, s), 5.40-5.83(1H, m), 5.67(1H, s), 6.77-7.67(5H, m)1201b 1.17-2.73(8H, m), 3.90(6H, s), 5.07-5.57(1H, m), 5.87(1H, s), 6.73-7.73(5H, m) mp 129.0-131.6.degree. C.1202a 1.17-2.50(8H, m), 3.90(6H, s), 5.33-5.83(1H, m), 5.68(1H, s), 6.73-7.57(4H, m)1202b 1.17-2.73(8H, m), 3.90(6H, s), 5.17-6.00(1H, m), 5.70(1H, s), 6.77-7.60(4H, m) mp 137.5-139.5.degree. C.1211a 1.12-2.35(8H, m), 3.88(6H, s), 4.33-4.63(2H, m), 4.93- 5.43(2H, m), 5.63(1H, s), 5.52-6.17(2H, m)1211b 1.00-2.50(8H, m), 3.90(6H, s), 4.32-4.62(2H, m), 4.97-5.43(2H, m), 5.63(1H, s), 5.47-6.13(2H, m) mp 41.0-42.5.degree. C.1212a 0.77-2.33(8H, m), 2.40(1H, t, J=2Hz), 3.93(6H, s), 4.63(2H, d, J=2Hz) 5.33-5.77(1H, m), 5.67(1H, s)1212b 1.33-2.50(8H, m), 2.35(1H, t, J=2Hz), 3.90(6H, s), 4.65(2H, d, J=2Hz) 5.07-5.57(1H, m), 5.97(1H, s)1215b white powder1216b white powder1220b 1.69(3H, s), 1.72(3H, s), 1.13-2.43(8H, m), 3.89(6H, s), 5.06-5.79(1H, m), 5.66(1H, s) mp 109.3-112.1.degree. C.1222b 1.10-2.44(12H, m), 3.89(6H, s), 4.50-5.00(1H, m), 5.05-5.84(1H, m), 5.64(1H, s) mp 74.4-76.2.degree. C.1223b 1.06-2.42(14H, m), 3.91(6H, s), 4.11(2H, q, J=6.6Hz), 4.84-5.89((2H, m), 5.65(1H, s)1224b 0.93-2.53(8H, m), 1.23(3H, t, J=7Hz), 3.90(6H, s), 4.17(2H, q, J=7Hz), 4.63(2H, s), 5.05-5.87(1H, m), 5.67(1H, s) mp 81.6-84.6.degree. C.1225b 1.39-2.46(8H, m), 2.13(3H, s), 3.88(6H, s), 4.63(2H, s), 5.08-5.82(1H, m), 5.67(1H, s) mp 106.6-107.9.degree. C.1226b 1.20-2.41(8H, m), 3.88(6H, s), 4.48(2H, q, J=8Hz, ), 5.06-5.81(1H, m), 5.65(1H, s) mp 75.1-77.4.degree. C.1227b 1.27-2.41(8H, m), 3.88(6H, s), 4.74(2H, s), 5.00-5.75(1H, m) 5.66(1H, s) mp 94.7-96.2.degree. C.1228b 1.34-2.46(8H, m), 3.91(6H, s), 4.69(2H, s), 5.33(1H, s), 5.46(1H, s) 5.09-5.81(1H, m), 5.67(1H, s) mp 52.3-54.8.degree. C.1229b 1.16-2.41(8H, m), 3.86(6H, s), 4.54(2H, dd, J=8Hz, 12Hz), 5.00-5.78(1H, m), 5.65(1H, s), 5.78-6.42(2H, m) mp 59.3-61.6.degree. C.1230b 1.12-2.39(8H, m), 3.91(6H, s), 4.62(2H, q, J=2.4Hz), 5.09-5.84(1H, m), 5.65(1H, s)1231b 1.13-2.38(8H, m), 3.89(6H, s), 5.03(1H, s), 5.08(1H, s), 5.17-5.83(1H, s), 5.66(1H, s), 6.26(2H, m), 7.25(1H, m)1232b 1.21-2.49(9H, m), 2.44(2H, dt, J=3Hz, 6.4Hz), 3.90(6H, s), 4.21(2H, t, J=6.4Hz), 5.04-5.76(1H, m), 5.66(1H, s)1233b 1.19-2.36(16H, m), 3.92(6H, s), 5.00-5.76(1H, m), 5.17(1H, m), 5.67(1H, s) mp 91.5-93.9.degree. C.1234b 1.33-2.40(8H, m), 3.37(2H, t, J=6Hz), 3.88(6H, s), 4.37(2H, t, J=6Hz), 5.02-5.37(1H, m), 5.63(1H, s)1235b 1.24-2.41(8H, m), 3.29-3.58(2H, m), 3.89(6H, s), 4.24(2H, t, J=6Hz), 5.05-5.78(1H, m), 5.65(1H, s)1236b 1.40-2.42(18H, m), 3.90(6H, s), 4.58-5.00(1H, m), 5.08-5.82(1H, m), 5.66(1H, s)1237b 0.09-0.65(4H, m), 0.72-1.30(1H, m), 1.32-2.42(8H, m), 3.89(6H, s), 3.99(2H, d, J=2Hz), 5.09-5.85(1H, m), 5.65(1H, s) mp 73.6-75.5.degree. C.1238b 1.00-2.40(11H, m), 3.92(6H, s), 4.30-4.77(2H, m), 5.00-6.03(3H, m), 5.67(1H, s)1239b 1.03-2.43(14H, m), 3.90(6H, s), 4.37-4.75(2H, m), 4.93-5.83(2H, m), 5.65(1H, s)1240b 0.77-2.50(8H, m), 3.87(6H, s), 4.73(2H, s), 4.90-5.87(1H, m), 5.63(1H, s)1241b 1.10-2.63(8H, m), 3.80(6H, s), 4.60-4.83(2H, m), 4.93-5.77(1H, m), 5.57(1H, s), 6.08(1H, dt, J=16Hz, 6Hz), 6.52(1H, d, J=16Hz), 7.23(5H, s) mp.71.2-73.2.degree. C.1242b 0.93-2.57(8H, m), 3.33(3H, s), 3.37(3H, s), 4.02(6H, s), 5.07-5.97(1H, m) 4.22(1H, d, J=6Hz), 4.23(1H, d, J=6Hz), 4.58(1H, dd, J=6Hz, 6Hz), 5.78(1H, s) mp 68.6-70.0.degree. C.1243b 1.17-2.40(8H, m), 3.91(6H, s), 4.11(2H, s), 4.47-4.69(1H, m), 4.81-5.01(1H, m), 5.10-5.84(1H, m), 5.68(1H, s) mp 108.7-111.1.degree. C.1244b 1.28-2.33(14H, m), 3.87(6H, s), 5.06-6.03(4H, m), 5.62(1H, s)1245b 1.17-2.37(8H, m), 3.86(6H, s), 5.00-5.77(1H, m), 5.20(1H, s), 5.26(1H, s), 5.61(1H, s), 6.70-7.33(3H, m)1246b 1.10(3H, t, J=7Hz), 1.10-2.87(8H, m), 3.55(2H, q, J=7Hz), 3.87(6H, s), 4.87-5.78(1H, m), 5.27(2H, s), 5.63(1H, s)1247b 0.73-2.57(8H, m), 3.87(6H, s), 4.90-5.53(1H, m), 5.67(1H, s), 7.23-7.80(5H, m), 8.33(1H, s) mp 128.5-129.0.degree. C.1248b 0.93-2.60(8H, m), 1.97(3H, s), 2.00(3H, s), 3.88(6H, s), 5.03-5.83(1H, m), 5.63(1H, s)1249b 0.85-2.58(10H, m), 1.12(3H, t, J=7Hz), 1.95(3H, s), 3.88(6H, s), 5.05-5.85(1H, m), 5.65(1H, s) mp 89.4-91.3.degree. C.1250b 0.73-2.57(16H, m), O.93(6H, t, J=7Hz), 3.90(6H, s), 5.00-5.87(1H, m), 5.63(1H, s)1251b 0.95-2.63(8H, m), 1.24(6H, d, J=7Hz), 1.27(6H, d, J=7Hz), 2.75(1H, sep, J=7Hz), 2.98(1H, sep, J=7Hz), 3.95(6H, s), 4.88-5.90(1H, m), 5.73(1H, s) mp 133.2-135.9.degree. C.1252b 0.93-2.87(18H, m), 3.87(6H, s), 4.87-5.83(1H, m), 5.63(1H, s) mp 106.3-108.6.degree. C.1253b 0.93-2.46(8H, m), 1.29(3H, t, J=6.4Hz), 2.02(3H, s), 3.89(6H, s), 4.14(2H, q, J=6.4Hz), 5.06-5.76(1H, m), 5.60(1H, s) mp 93.2-95.5.degree. C.1276a 0.90(3H, d, J=7Hz), 1.05-2.81(7H, m), 3.87(6H, s), 5.29-5.68(1H, m), 5.62(1H, s), 8.12(1H, s) (axial methyl group)1276b 0.77-1.22(3H, m), 1.2-2.47(7H, m), 3.87(6H, s), 5.0-5.73(1H, m), 5.63(1H, s) (equatrial methyl group)1278a 0.93(3H, d, J=6.4Hz), 1.07(3H, t, J=7.2Hz), 1.27-2.49(7H, m), 3.88- 4.12(2H, m), 3.9(6H, s), 5.55-5.61(1H, m), 5.68(1H, s) (axial methyl group)1278b 1.03(3H, d, J=4.4Hz), 1.12-2.27(7H, m), 3.9(6H, s), 4.26-4.43(2H, m) 5.41-5.49(1H, m), 5.68(1H, s) (equatrial methyl group)1295a 0.95(9H, s), 1.08(3H, t, J=7Hz), 0.78-2.55(7H, m), 3.88(6H, s), 4.0 (2H, q, J=7Hz), 5.35-5.74(1H, m), 5.64(1H, s) (equatrial t-butyl group)1411a 1.40-2.83(10H, m), 3.88(6H, s), 4.18(1H, s), 4.82-5.62(1H, m), 5.67(1H, s) mp 177.5-179.0.degree. C.1411b 1.43-2.52(10H, m), 3.87(6H, s), 5.02-5.63(1H, m), 5.65(1H, s), 7.58(1H, s) mp 113.0-115.5.degree. C.1412a 1.15-2.70(10H, m), 3.85(3H, s), 3.88(6H, s), 5.08-5.93(1H, m), 5.67(1H, s)1412b 1.47-2.47(10H, m), 3.70(3H, s), 3.87(6H, s), 5.08-5.78(1H, m), 5.63(1H, s) mp 85.5-86.0.degree. C.1413a 1.27-2.73(10H, m), 1.32(3H, t, J=7Hz), 3.88(6H, s), 4.30(2H, q, J=7Hz), 5.03-5.56(1H, m), 5.65(1H, s)1413b 1.57-2.43(10H, m), 1.17(3H, t, J=7Hz), 3.90(6H, s), 4.17(2H, q, J=7Hz), 5.07-5.43(1H, m), 5.43(1H, s)1427a 1.35-2.40(12H, m), 3.88(6H, s), 4.63(1H, s), 5.53-6.00(1H, m), 5.68(1H, s) mp 179-180.5.degree. C.1428a 1.0-2.77(12H, m), 3.83(3H, s), 3.90(6H, s), 5.07-6.02(1H, m), 5.48(1H, s) mp 90.5-92.0.degree. C.1454b 1.42-2.47(8H, m), 3.88(6H, s), 5.20-5.80(1H, m), 5.65(1H, S) 7.15(1H, s)1455b 1.18(3H, t, J=7.0Hz), 1.33-2.37(8H, m), 3.90(6H, s), 4.13(2H, q, J=7.0Hz), 5.52-5.82(1H, m), 5.65(1H, s)1467b 1.07-2.40(8H, m), 2.42(1H, t, J=2.5Hz), 3.91(6H, s), 4.71(2H, d, J=2.5Hz), 5.57-5.85(1H, m), 5.67(1H, s)1496 1.1-3.3(9H, m), 3.75(3H, s), 3.90(6H, s), 5.78(1H, s)1563a 1.35-2.73(6H, m), 3.93(6H, s), 4.03-4.77(1H, m), 4.63(2H, s), 5.9 (1H, s), 7.67(1H, s)1563b 1,35-2.82(6H, m), 3.9(6H, s), 3.93-4.79(1H, m), 4.62(2H, s), 5.9(1H, s) 8.9(1H, s)1564b 1.3-2.58(6H, m), 3.77(3H, s), 3.93(6H, s), 4.04-4.79(1H, m), 4.55(2H, s), 5.87(1H, s)1580a 1.11-2.75(8H, m), 3.59-4.86(1H, m), 3.92(6H, s), 4.71(2H, d, J=8Hz), 5.88(1H, s)1580b 1.08-2.37(8H, m), 3.52-4.38(1H, m) 3.88(6H, s), 4.75(2H, s) 5.81 (1H, s)1582a 0.95-2.73(8H, m), 1.28(3H, t, J=7Hz), 3.57-4.72(1H, m), 3.9(6H, s), 4.21(2H, q, J=7Hz), 4.57(2H, s), 5.9(1H, s)1582b 0.8-2.36(8H, m), 1.28(3H, t,J=7Hz), 3.55-4.83(1H, m), 3.91(6H, s), 4.2(2H, q, J=7Hz), 4.52(2H, s), 5.88(1H, s)__________________________________________________________________________
TABLE 9__________________________________________________________________________Compound .sup.1 H-NMR(.delta. ppm, CDCl.sub.3)No. and/or Physical data__________________________________________________________________________2021a 6.16(1H, s), 5.3-5.8(1H, m), 3.91(3H, s), 3.54(3H, s), 2.29 (3H, s), 1.6-2.5(6H, m)2021b 6.16(1H, s), 5.3-5.8(1H, m), 3.91(3H, s), 3.75(3H, s), 2.32 (3H, s), 1.6-2.5(6H, m)2039 5.84(1H .times. 2, s), 5.1-5.6(1H .times. 2, m), 3.94(3H .times. 2, s), 3.80(3H, s), 3.66(3H, s), 1.4-2.5(6H .times. 2, 2)2057a 6.34(1H, s), 5.3-5.8(1H, m), 3.92(3H, s), 3.59(3H, s), 1.7-2.2(6H, m)2057b 6.33(1H, s), 5.3-5.8(1H, m), 3.92(3H, s), 3.77(3H, s), 1.7-2.5(6H, m)2058a 6.35(1H, s), 5.3-5.7(1H, m), 4.11(2H, q, J=7Hz), 3.93(3H, s), 1.5-2.3(8H, m), 1.21(3H, t, J=7Hz)2093a 6.32(1H, s), 5.3-5.7(1H, m), 4.34(2H, q, J=7Hz), 3.63(3H, s), 1.7-2.5(6H, m), 1.37(3H, t, J=7Hz)2093b 6.32(1H, s), 5.2-5.7(1H, m), 4.35(2H, q, J=7Hz), 3.81(3H, s), 1.6-2.6(6H, m), 1.36(3H, t, J=7Hz)2111a 5.3-5.7(1H, m), 5.64(1H, s), 4.34(2H, q, J=7Hz), 3.88(3H, s), 3.56(3H, s), 1.6-2.5(6H, m), 1.34(3H, t, J=7Hz)2111b 5.3-5.7(1H, m), 5.63(1H, s), 4.20(2H, q, J=7Hz), 3.88(3H, s), 3.74(3H, s), 1.6-2.5(6H, m), 1.34(3H, t, J=7Hz)2128b 5.61(1H, s), 5.2-5.6(1H, m), 4.28(4H, q, J=7Hz), 1.7-2.5 (6H, m), 1.34(6H, t, J=7Hz)2129a 5.3-5.7(1H, m), 5.58(1H, s), 4.29(4H, q, J=7Hz), 3.55(3H, s), 1.6-2.5(6H, m), 1.34(6H, t, J=7Hz)2129b 5.3-5.7(1H, m), 5.57(1H, s), 4.25(4H, q, J=7Hz), 3.72(3H, s), 1.6-2.5(6H, m), 1.34(6H, t, J=7Hz)2142b 5.0-5.9(4H, m), 5.61(1H, s), 4.61(2H, m), 4.27(4H, q, J=7Hz), 1.6-2.5(6H, m), 1.35(6H, t, J=7Hz)2143b 5.2-5.7(1H, m), 5.61(1H, s), 4.75(2H, d, J=2Hz), 4.26(4H, q, J=7Hz), 2.44(1H, t, J=2Hz), 1.5-2.4(6H, m), 1.34(6H, t, J=7Hz)2147a 5.3-5.7(1H, m), 5.62(1H, s), 4.22(4H, t, J=6Hz), 3.60(3H, s), 1.2-2, 4(10H, m), 1.01(6H, t, J=7Hz)2147b 5.3-5.8(1H, m), 5.60(1H, s), 4.16(4H, t, J=6Hz), 3.73(3H, s), 1.3-2.6(10H, m), 0.98(6H, t, J=7Hz) mp 40-40.5.degree. C.2164a 5.3-5.6(1H, m), 5.55(1H, s), 5.20(2H, sep, J=6Hz), 1.7-2.6 (6H, m), 1.32(12H, d, J=6Hz)2164b 5.54(1H, s), 5.1-5.4(1H, m), 5.17(2H, sep, J=6Hz), 1.7-2.6 (6H, m), 1.29(12H, d, J=6Hz)2165a 5.3-5.7(1H, m), 5.54(1H, s), 5.24(2H, sep, J=6Hz), 3.61(3H, s), 1.6-2.5(6H, m), 1.32(12H, d, J=6Hz)2165b 5.3-5.6(1H, m), 5.55(1H, s), 5.29(2H, sep, J=6Hz), 3.74(3H, s), 1.6-2.5(6H, m), 1.36(12H, d, J=6Hz) mp 66-67.degree. C.2183b 7.38(2H, t, J.sub.CF =82Hz), 6.02(1H, s), 5.2-5.7(1H, m), 3.77(3H, s), 1.6-2.7(6H, m)2344a 6.34(1H, s), 5.10-5.60(1H, m), 3.95(3H, s), 1.26-2.30(8H, m)2344b 6.32(1H, s), 5.00-5.70(1H, m), 3.92(3H, s), 1.25-2.45(8H, m)2345a 6.34(1H, s), 5.25-5.65(1H, m), 3.96(3H.s), 3.70(3H, s), 1. 30-2.30 (8H, m)2345b 6.37(1H, s), 5.1-5.8(1H, m), 3.95(3H, s), 3.74(3H, s), 1.4-2.3(8H, m)2346a 6.32(1H, s), 5.3-5.6(1H, m), 4.12(2H, q, J=7Hz), 3.94(3H, s), 1.4-2.3(8H, m), 1.21(3H, t, J=7Hz)2346b 6.32(1H, s), 5.1-5.8(1H, m), 4.14(2H, q, J=7Hz), 3.91(3H, s), 1.4-2.3(8H, m), 1.17(3H, t, J=7Hz)2348a 6.34(1H, s), 5.30-5.65(1H, m), 4.97(1H, sep, J=7Hz), 3.93(3H, s), 1.40-2.30(8H, m), 1.17(3H, d, J=7Hz), 1.15(3H, d, J=7Hz)2351a 6.31(1H, s), 4.65- 5.70(2H, m), 3.92(6H, s), 0.63-2.24(16H, m)2351b 6.34(1H, s), 4.66-5.85(2H, m), 3.93(6H, s), 0.49-2.29(16H, m)2353a 6.34(1H, s), 5.26-5.62(1H, m), 4.10-4.42(2H, m), 3.93(6H, s), 3.57(2H, t, J= 7Hz), 1.17-2.35(8H, m)2380a 6.33(1H, s), 5.2-5.5(1H, m), 4.28(2H, q, J=7Hz), 1.6-2.3 (8H, m), 1.37(3H, t, J=7Hz)2382a 6.31(1H, s), 5.3-5.7(1H, m), 4.37(2H, q, J=7Hz), 4.13(2H, q, J=7Hz), 1.5-2.3(8H, m), 1.37(3H, t, J=7Hz), 1.15(3H, t, J=7Hz)2382b 6.28(1H, s), 5.0-5.5(1H, m), 4.37(2H, q, J=7Hz), 4.14(2H, q, J=7Hz), 1.5-2.3(8H, m), 1.34(3H, t, J=7Hz), 1.16(3H, t, J=7Hz)2416a 5.4-5.7(1H, m), 5.61(1H, s), 4.27(4H, q, J=7Hz), 1.5-2.3 (8H, m), 1.33(6H, t) mp 136.5-137.5.degree. C.2418a 5.58(1H, s), 5.3-5.6(1H, m), 4.28(4H, q, J=7Hz), 4.07(1H, q, J=7Hz), 4.04(1H, q, J=7Hz), 1.5-1.9(8H, m), 1.34(6H, t, J=7Hz), 1.14(3H, t, J=7Hz)2418b 5.4-5.7(1H, m), 5.60(1H, s), 4.29(4H, q, J=7Hz), 4.12(2H, q, J=7Hz), 1.5-2.3(8H, m), 1.33(6H, t, J=7Hz), 1.14(3H, t, J=7Hz)2434b 5.64(1H, s), 5.0-5.5(1H, m), 4.17(4H, t, J=6Hz), 1.3- 2.1 (12H, m), 0.98(6H, t, J=7Hz)2436a 5.4-5.7(1H, m), 5.59(1H, s), 4.17(4H, t, J=6Hz), 4.09(2H, q, J=7Hz), 1.2-2.3(12H, m), 1.15(3H, t, J=7Hz), 0.98(6H, t, J=7Hz)2436b 5.62(1H, s), 5.0-5.5(1H, m), 4.22(4H, t, J=6Hz), 4.15(2H, q, J=7Hz), 1.3-2.3(12H, m), 1.17(3H, t, J=7Hz), 0.98(6H, t, J=7Hz)2489a 6.16(1H, s), 5.25-5.70(1H, m), 3.91(3H, s), 3.65(3H, s), 2.49(3H, s), 1.37-2.25(8H, m)2508a 6.81(1H, s), 5.30-5.70(1H, s), 4.17(1H, q, J=7Hz), 4.10(1H, q, J=7Hz), 2.51(3H, s), 1.40-2.25(8H, m), 1.19(3H, t, J=7Hz)2508b 6.79(1H, s), 5.10-5.70(1H, m), 4.16(2H, q, J=7Hz), 2.52(3H, s), 1.20(3H, t, J=7Hz), 1.40-2.35(8H, m)2560a 5.30(1H, s), 5.25-5.60(1H, m), 4.05(1H, q, J=7Hz), 4.01(1H, q, J=7Hz), 2.99(6H, s), 1.35-2.20(8H, m), 1.13(3H, t, J=7Hz)2560b 5.33(1H, s), 5.10-5.65(1H, m), 4.12(2H, q, J=7Hz), 3.88(3H, s), 3.01(6H, s), 1.40-2.30(8H, m), 1.16(3H, t, J=7Hz)__________________________________________________________________________
TABLE 10__________________________________________________________________________Compound .sup.1 H-NMR(.delta. ppm, CDCl.sub.3)No. and/or Physical data__________________________________________________________________________3003a 5.4-5.9(1H, m), 4.00(6H, s), 3.68(3H, s), 1.7-2.6(6H, m)3003b 5.4-5.9(1H, m), 4.00(6H, s), 3.72(3H, s), 1.7-2.6(6H, m)3077a 6.29(1H, s), 5.3-5.9(1H, m), 3.68(3H, s), 2.49(3H, s), 1.6-2.6(6H, m)3077b 6.42(1H, s), 5.3-5.9(1H, m), 3.81(3H, s), 2.49(3H, s), 1.7-2.6(6H, m)3292b 6.35(1H, s), 5.4-5.9(1H, m), 2.49(3H, s), 1.3-2.4(8H, m)3294a 6.36(1H, s), 5.3-5.7(1H, m), 4.16(2H, q, J=7Hz), 2.49(3H, s), 1.4-2.2(8H, m), 1.22(3H, t, J=7Hz)3294b 6.39(1H, s), 5.1-5.9(1H, m), 4.17(2H, q, J=7Hz), 2.51(3H, s), 1.3-2.4(8H, m), 1.19(3H, t, J=7Hz)3310a 5.70(1H, s), 5.25-5.75(1H, m), 3.90(3H, s), 2.52(3H, s), 1.25-2.30(8H, m)3312b 5.69(1H, s), 5.05-5.70(1H, m), 4.15(2H, q, J=7Hz), 3.89(3H, s), 2.50(3H, s), 1.20-2.35(8H, m), 1.16(3H, t)3330a 6.83(1H, s), 5.30-5.55(1H.m), 4.22(2H.q.J=7Hz), 3.33(3H, s), 1.30-2.40(m, 8H), 1.28(3H, t)3366a 6.38(1H, s), 5.20-5.70(1H, m), 3.96(3H, s), 3.73(3H, s), 1.20-2.30(8H, m)3379a 6.30(1H, s), 5.25-5.65(1H, m), 4.64(2H, d, J=3Hz), 3.93(3H, s), 2.36(1H, t, J=3Hz), 1.25-2.45(8H, m)3379b 6.38(1H, s), 5.15- 5.80(1H, m), 4.69(2H, d, J=3Hz), 4.00(3H, s), 2.38(1H, t, J=3Hz), 1.26-2.60(8H, m)__________________________________________________________________________
TABLE 11__________________________________________________________________________Compound .sup.1 H-NMR(.delta. ppm, CDCl.sub.3)No. and/or Physica1 data__________________________________________________________________________4001b 1.61-2.73(6H, m), 3.90(6H, s), 5.63(1H, s), 5.27-5.90(1H, m), 5.90-6.57(2H, br) mp 163.2-165.0.degree. C.4002b 1.54-1.70(6H, m), 3.79(3H, d, J=5Hz), 3.90(6H, s), 5.64(1H, s), 5.27-5.97(1H, m), 6.20-6.67(1H, bs) mp 129.0-131.5.degree. C.4003a 1.01(3H, t, J=7Hz), 1.60-2.50(6H, m), 3.20(2H, q, J=7Hz), 3.90(6H, s), 5.63(1H, s), 5.20-5.84(1H, m), 6.22(1H, bs) mp 118.3-119.5.degree. C.4003b 1.06(3H, t, J=7.6Hz), 1.53-2.70(6H, m), 3.26(2H, q, J=7.6Hz), 3.92(6H, s), 5.64(1H, s), 5.30-5.96(1H, m), 6.45(1H, bs)4009a 1.25(9H, s), 1.50-2.50(6H, m), 3.90(6H, s), 5.65(1H, s), 5.17-5.83(1H, m), 6.00(1H, bs)4009b 1.28(9H, s), 1.61-2.68(6H, m), 3.94(6H, s), 5.64(1H, s), 5.31-6.0(1H, m), 6.23(1H, bs)4010b 1.67-2.67(6H, m), 2.73-3.20(6H, m), 3.87(6H, s), 5.62(1H, s), 5.47-6.05(1H, m)4013b 1.57-2.73(6H, m), 3.81(6H, s), 5.61(1H, s), 5.40-6.03(1H, m), 7.00-7.63(5H, m), 7.88-8.23(1H, bs) mp 154.0-157.5.degree. C.4035b 1.64-2.72(6H, m), 3.88(6H, s), 5.30-6.00(1H, m), 5.61(1H, s), 9.09(1H, bs)4036b 1.63-2.87(6H, m), 3.38(3H, d, J=3Hz), 3.88(6H, s), 5.73(1H, s), 5.40-6.00(1H, m), 8.17-8.55(1H, bs) mp 124.0-127.5.degree. C.4037b 1.59-2.82(6H, m), 3.67(3H, s), 3.92(6H, s), 5.66(1H, s), 5.29-5.99 (1H, m), 5.29-5.99(1H, m), 8.96-9.24(1H, bs) mp 114.5-117.5.degree. C.4040b 1.65-2.75(6H, m), 3.91(6H, s), 4.80(2H, s), 5.31-5.98(1H, m), 5.68 (1H, s), 7.21-7.40(5H, m), 8.80(1H, bs)4048b 1.70-2.77(6H, m), 3.76(3H, s)3.94(6H, s), 4.41(2H, s), 5.70(1H, s), 5.33-6.00(1H, m), 9.43-9.73(1H, bs) mp 68.0-70.2.degree. C.4071b 1.68-2.72(6H, m), 2.48(6H, s), 3.91(6H, s), 5.65(1H, s), 5.35-6.05 (1H, s), 7.05-7.18(1H, m)4079b 1.61-2.69(6H, m), 3.89(6H, s), 5.66(1H, s), 5.33-5.89(1H, m)4095b 1.67-2.57(6H, m), 3.63(3H, s), 3.90(6H, s), 4.49(2H, s), 5.65(1H, s), 5.47-6.14(1H, m), 7.72(1H, bs)4096b 1.56-2.59(6H, m), 3.69(3H, s), 3.92(6H, s), 4.10(3H, s), 4.44(2H, s), 5.66(1H, s), 5.39-5.92(1H, m) mp 72.5-74.0.degree. C.4228a 1.08(3H, t, J=7Hz), 1.71-2.55(6H, m), 2.74(2H, q, J=7Hz), 3.92(6H, s), 5.61(1H, s), 5.33-5.85(1H, m)4228b 1.20(3H, t, J=7.6Hz), 1.60-2.56(6H, m), 2.77(2H, q, J= 7.6Hz), 3.90(6H, s), 5.65(1H, s), 5.30-5.90(1H, m)4230a 1.11(3H, d, J=8Hz), 1.24(3H, d, J=8Hz), 1.62-2.75(6H, m), 3.48(1H, sep, J=8Hz), 3.59(6H, s), 5.64(1H, s), 5.32-5.88(1H, m)4230b 1.20(3H, d, J=7Hz), 1.30(3H, d, J=7Hz), 1.67-2.53(6H, m), 3.50(1H, sep, J=7Hz), 3.88(6H, s), 5.63(1H, s), 5.33-5.90(1H, m)4234b 1.41(9H, s), 1.97-2.83(6H, m), 3.88(6H, s), 5.62(1H, s), 5.37-5.95(1H, m) mp 81.5-83.2.degree. C.4239a 1.72-2.72(6H, m), 3.93(6H, s), 5.65(1H, s), 5.40-5.93(1H, m), 7.03-7.77(3H, m), 8.52(1H, m) mp 92.0-94.5.degree. C.4239b 1.54-2.70(6H, m), 3.75(6H, s), 5.66(1H, s), 5.30-5.90(1H, m), 7.05-7.84(3H, m), 8.57(1H, m)4275b 1.00-2.83(8H, m), 3.90(6H, s), 4.93-5.83(1H, m), 5.63(1H, s), 6.00(1H, bs), 6.53(1H, bs)4276a 1.00-2.67(8H, m), 2.87(3H, d, J=6Hz), 3.90(6H, s), 4.97-5.63 (1H, m), 5.68(1H, s), 6.50(1H, bs) mp 147.2-149.5.degree. C.4276b 1.02-2.65(8H, m), 2.82(3H, d, J=6Hz), 3.90(6H, s), 4.95-5.85(1H, m), 5.65(1H, s), 6.53(1H, bs)4277a 1.22(3H, t, J=7Hz), 1.32-2.50(8H, m), 3.17(1H, q, J=7Hz), 3.28(1H, q, J=7Hz), 3.87(6H, s), 4.87-5.60(1H, m), 5.63(1H, s), 6.43(1H, bs) mp 99.5-100.5.degree. C.4277b 1.07(3H, t, J=6Hz), 1.17-2.48(8H, m), 3.15(1H, q, J=6Hz), 3.27(1H, q, J=6Hz), 3.87(1H, s), 4.92-5.37(1H, m), 5.60(1H, s), 6.47(1H, bs) mp 130.5-133.5.degree. C.4283a 1.40(9H, s), 1.52-2.52(8H, m), 3.88(6H, s), 5.02-5.48(1H, m), 5.65(1H, s), 6.15(1H, bs)4283b 1.28(9H, s), 1.37-2.53(8H, m), 3.87(6H, s), 4.93-5.33(1H, m), 5.62(1H, s), 6.30(1H, bs)4287b 1.10-2.70(8H, m), 3.87(6H, s), 5.03-5.97(1H, m), 5.60(1H, s), 6.87-7.70(5H, m), 7.87-8.53(1H, m) mp 189.9-193.6.degree. C.4293b 1.35(3H, t, J=7Hz), 1.41-2.53(8H, m), 3.87(6H, s), 3.95(2H, q, J=7Hz), 5.00-5.93(1H, m), 5.58(1H, s), 6.74(2H, d, J=9Hz), 7.32(2H, d, J=9Hz), 8.09(1H, bs) mp 152.5-155.3.degree. C.4295b 1.32-2.53(8H, m), 3.90(6H, s), 5.07-5.90(1H, m), 5.62(1H, s), 7.27-7.95(4H, m), 8.43(1H, m)4297b 1.16-2.40(8H, m), 3.26(3H, s), 3.93(6H, s), 5.13-5.86(1H, m), 5.68(1H, s), 7.13-7.53(5H, m)4305b 1.31-2.41(8H, m), 3.88(6H, s), 4.33(1H, s), 4.42(1H, s), 5.05-5.81 (1H, m), 5.63(1H, s), 6.17(2H, m), 7.22(1H, m)4309b 1.25-2.38(8H, m), 3.85(6H, s), 5.00-5.73(1H, m), 5.61(1H, s), 9.22(1H, bs) mp 184.2-187.4.degree. C.4311b 1.26-2.48(8H, m), 3.68(3H, s), 3.92(6H, s), 5.05-5.81(1H, m), 5.68(1H, s), 9.32(1H, bs)4314b 1.20-2.40(8H, m), 3.87(6H, s), 4.76(1H, s), 4.78(1H, s), 5.00-5.77 (1H, m), 5.64(1H, s), 7.20-7.53(5H, m), 8.88(1H, bs)4322b 1.33-2.80(8H, m), 3.83(3H, s), 3.92(6H, s), 4.43(2H, s), 5.00-5.93 (1H, m), 5.72(1H, s), 9.67(1H, bs)4325b 1.30-2.50(8H, m), 2.22(3H, s), 3.92(6H, s), 5.03-5.83(1H, m), 5.68(1H, s), 9.98(1H, bs) mp 158.2-160.3.degree. C.4332b 1.28(9H, s), 1.44-2.44(8H, m), 3.91(6H, s), 5.01-5.74(1H, m), 5.65(1H, s), 9.78(1H, bs) mp 170.6-173.9.degree. C.4344b 1.33-2.57(8H, m), 2.47(3H, s), 3.90(6H, s), 5.03-5.80(1H, m), 5.63(1H, s), 7.25(1H, d, J=8Hz), 7.62(1H, d, J=8Hz) mp 166.1-168.3.degree. C.4346b 1.21(3H, t, J=7.8Hz), 1.38-2.48(8H, m), 3.91(6H, s), 4.14(2H, q, J= 7.8Hz), 5.10-5.91(1H, m), 5.67(1H, s), 6.98(1H, bs), 8.55(1H, bs)4347b 1.27(3H, t, J=7Hz), 1.19-2.47(8H, m), 3.04(3H, s), 3.37(3H, s), 3.86(6H, s), 4.13(2H, q, J=7Hz), 4.99-5.84(1H, m), 5.62(1H, s)4348b 1.27(3H, t, J=7Hz), 1.33-2.76(8H, m), 3.55(2H, s), 3.92(6H, s), 4.19(2H, q, J=7Hz), 5.01-5.79(1H, m), 5.67(1H, s), 8.33(1H, bs) mp 116.8-118.5.degree. C.4350b 1.26(3H, t, J=6.6Hz), 1.32-2.52(8H, m), 3.86(6H, s), 3.82-4.44 (4H, m), 5.06-5.82(1H, m), 5.63(1H, s), 7.09(1H, bs) mp 159.1-161.3.degree. C.4351b 0.73(6H, t, J=7Hz), 1.33-2.70(12H, m), 3.74(3H, s), 3.90(6H, s), 4.95-5.76(1H, m), 5.63(1H, s), 7.45(1H, bs) mp 106.2-108.7.degree. C.4352b 1.22-2.43(8H, m), 3.91(6H, s), 4.92-5.75(1H, m), 5.66(1H, s),4353b 1.43-2.46(8H, m), 3.85(6H, s), 5.12-5.86(1H, m), 5.57(1H, s), 6.90(1H, d, J=3.6Hz), 7.58(1H, d, J=3.6Hz), 10.96(1H, bs) mp 181.0-181.3.degree. C.4354b 1.34-2.37(8H, m), 3.83(6H, s), 5.14-5.74(1H, m), 5.57(1H, s), 8.76(1H, s) mp 215.2-215.8.degree. C.4355b 1.40-2.50(8H, m), 3.86(6H, s), 5.00-5.83(1H, m), 5.59(1H, s), mp 164.2-165.0.degree. C.4356b 1.36-2.49(8H, m), 3.83(6H, s), 5.00-5.91(1H, m), 5.56(1H, s), 6.81-7.11(1H, m), 7.39-7.78(1H, m), 7.93-8.31(2H, m), 8.78(1H, bs) mp 148.6-149.2.degree. C.4358b 1.37-2.40(8H, m), 3.84(6H, s), 5.00-5.83(1H, m), 5.56(1H, s), 7.20-7.51(2H, m), 8.25-8.58(2H, m) mp 145.1-148.5.degree. C.4359b 1.14-2.44(14H, m), 2.48-2.91(4H, m), 3.90(6H, s), 5.01-5.81(1H, m), 5.66(1H, s), 7.25(1H, bs) mp 182.2-183.0.degree. C.4360b 1.40-2.67(8H, m), 3.88(6H, s), 5.05-5.91(1H, m), 5.59(1H, s), 7.03-7.99(4H, m), 10.15(1H, bs)4361b 1.33-2.46(8H, m), 3.89(6H, s), 5.01-5.76(1H, m), 5.64(1H, s), 6.53-6.79(2H, m), 7.11-7.44(1H, m), 7.96-8.13(1H, m) mp 196.5-198.9.degree. C.4379b 1.25-2.63(8H, m), 3.88(6H, s), 5.01-5.84(1H, m), 5.68(1H, s), 7.30(2H, bs) mp 189.1-192.6.degree. C.4396b 1.04-2.38(8H, m), 3.47(3H, s), 3.49(3H, s), 3.91(6H, s), 5.68(1H, s), 5.76-5.79(1H, m)4500a 1.17(3H, t, J=7Hz), 1.35-2.23(8H, m), 2.82(2H, q, J=7Hz), 3.87(6H, s), 5.20-5.67(1H, m), 5.62(1H, s)4500b 1.13(3H, t, J=7Hz), 1.37-2.37(8H, m), 2.82(2H, q, J=7Hz), 3.90(6H, s), 4.97-5.40(1H, m), 5.63(1H, s) mp 75.0-77.0.degree. C.4502b 1.15(3H, d, J=7Hz), 1.27(3H, d, J=7Hz), 1.33-2.04(8H, m), 3.52(1H, sep, J=7Hz), 3.90(6H, s), 4.97-5.37(1H, m), 5.60(1H, s) mp 82.0-83.0.degree. C.4506a 1.42(9H, s), 1.47-2.23(8H, m), 3.90(6H, s), 5.27-5.70(1H, m), 5.63(1H, s)4508b 1.20-2.37(8H, m), 3.87(6H, m), 4.03(2H, s), 5.03-5.87(1H, m), 5.63(1H, s), 7.10(5H, s)4511a 1.30-2.35(8H, m), 3.90(6H, s), 5.13-5.82(1H, m), 5.70(1H, s), 7.17-8.00(3H, m), 8.58(1H, m)4511b 1.00-2.50(8H, m), 3.87(6H, s), 4.90-5.60(1H, m), 5.67(1H, s), 7.00-7.87(3H, m), 8.40-8.73(1H, m) mp 115.0-118.5.degree. C.4512b 0.86-2.36(8H, m), 3.86(6H, s), 4.05(2H, s), 5.06-5.81(1H, m), 5.63(1H, s), 6.00-6.34(2H, m), 7.15-7.36(1H, m)4526b 1.04-2.18(8H, m), 1.17(3H, d, J=7Hz), 1.26(3H, d, J=7Hz), 3.43-3.47 (1H, m), 3.91(6H, s), 5.63-5.67(1H, m), 5.67(1H, s)4556b 1.08-2.78(8H, m), 3.73(1H, s), 3.93(6H, s), 5.10-5.82(1H, m), 5.68(1H, s)4558a 0.87-3.03(8H, m), 1.27(3H, t, J=7Hz), 4.00(6H, s), 4.17(1H, q, J=7Hz), 4.23(1H, q, J=7Hz), 5.37-5.80(1H, m), 5.77(1H, s)4558b 1.00-2.60(8H, m), 1.23(3H, t, J=7Hz), 3.97(6H, s), 4.22(2H, q, J=7Hz), 5.03-5.87(1H, m), 5.73(1H, s)__________________________________________________________________________
TABLE 12__________________________________________________________________________Compound .sup.1 H-NMR(.delta. ppm, CDCl.sub.3)No. and/or Physica1 data__________________________________________________________________________5001 1.68(3H, d, J=21Hz), 3.87(6H, s), 4.62(2H, d, J=21Hz), 5.67(1H, s), 8.55(1H, s) mp 120.0-122.50.degree. C.5003 1.3(3H, t, J=7Hz), 1.68(3H, d, J=21Hz), 3.92(6H, s), 4.28(2H, q, J=7Hz), 4.67(2H, d, J=21Hz), 5.7(1H, s)5130 1.54(3H, d, J=7Hz), 3.9(6H, s), 5.23-6.02(1H, m), 5.72(1H, s), 11(1H, s) mp 124.0-126.0.degree. C.5132 1.25(3H, t, J=7Hz), 1.52(3H, d, J=6.4Hz), 3.95(6H, s), 4.28(2H, q, J=7Hz 5.33-6.13(1H, m), 5.75(1H, s) mp 36.0-37.0.degree. C.5156a 1.48(3H, d, J=6.4Hz), 1.7(3H, d, J=20Hz), 3.95(6H, s), 5.26-5.98(1H, m) 5.73(1H, s) mp 129.0-130.0.degree. C.5156b 1.45(3H, d, J=6Hz), 1.63(3H, d, J=21.2Hz), 3.88(6H, s), 5.08-5.87(1H, s), 5.67(1H, s), 10.6(1H, s) mp 141.5-144.2.degree. C.5157b 1.44(3H, d, J=6Hz), 1.63(3H, d, J=21Hz), 3.73(3H, s), 3.9(6H, s) 5.12-5.9(1H, m), 5.67(1H, S) mp 94.7-97.1.degree. C.5158a 1.4(3H, t, J=7Hz), 1.38(3H, d, J=6Hz), 1.63(3H, d, J=20.2Hz), 3.92(6H, s), 4.24(2H, q, J=7Hz), 5.2-5.97(1H, m), 5.68(1H, s)5158b 1.22(3H, t, J=7Hz), 1.45(3H, d, J=6Hz), 1.61(3H, d, J=21.6Hz), 3.93(6H, s), 4.22(2H, q, J=7Hz), 5.03-5.88(1H, m), 5.67(1H, s) mp 49.8-51.0.degree. C.5178b 1.43(3H, d, J=6Hz), 1.63(3H, d, J=22Hz), 2.70-3.57(6H, m), 3.88(6H, s), 5.22-6.13(1H, m), 5.65(1H, s)5181b 1.25(3H, d, J=6Hz), 1.3(3H, d, J=6Hz), 1.44(3H, d, J=6Hz), 1.55(3H, d, J=21Hz), 3.55-3.6(1H, m), 3.9(6H, s), 5.5-5.59(1H, m), 5.69(1H, s)5182a 1.03(3H, t, J=7Hz), 1.53(3H, d, J=4.4Hz), 1.63-2.53(2H, m), 3.93(6H, s) 5.05-6.03(1H, m), 5.72(1H, s), 9.38(1H, s) mp 147.0-148.5.degree. C.5182b 0.97(3H, t, J=7Hz), 1.44(3H, d, J=6Hz), 1.5-2.31(2H, m), 3.88(6H, s), 5.12-5.84(1H, m), 5.68(1H, s), 8.87(1H, s) mp 81.5-82.5.degree. C.5184a 0.94(3H, t, J=7.3Hz), 1.32(3H, t, J=7Hz), 1.38(3H, d, J=6Hz), 1.48-2.45(2H, m), 3.91(6H, s), 4.27(2H, q, J=7Hz), 5.07-5.98(1H, s), 5.68(1H, s)5260a 1.47(3H, d, J=6.4Hz), 2.33-3.07(2H, m), 3.92(6H, s), 4.94-5.35(2H, m), 5.35-6.02(1H, m), 5.35-6, 02(1H, m), 5.72(1H, s), 8.2(1H, s) mp 148.0-150.5.degree. C.5260b 1.47(3H, d, J=6.4Hz), 2.23-3.03(2H, m), 3.88(6H, s), 4.86-5.43(2H, m) 5.33-6.23(1H, m), 5.33-6, 23(1H, m), 5.70(1H, s), 9.37(1H, s) mp 106.0-109.0.degree. C.5262a 1.28(3H, t, J=7Hz), 1.39(3H, d, J=6.4Hz), 2.1-3.3(2H, m), 3.88(6H, s) 4.23(2H, q, J=7Hz), 4.83-5.27(2H, m, ), 5.27-6.13(1H, m), 5.27-6.13(1H, m), 5.97(1H, s)5262b 1.19(3H, t, J=7Hz), 1.43(3H, d, J=6.4Hz), 2.33-3.01(2H, m), 3.85(6H, s) 4.15(2H, q, J=7Hz), 4.82-5.30(2H, m, ), 5.3-6.15(1H, m), 5.30-6.15(1H, m), 5.62(1H, s)5286a 1.47(3H, d, J=6Hz), 1.95-2.27(1H, m), 2.6--3.43(2H, m), 3.93(6H, s) 5.23-6.1(1H, m), 5.75(1H, s) mp 164.5-165.0.degree. C.5286b 1.47(3H, d, J=6Hz), 2, 28-2.39(1H, m), 2.58-3.43(2H, m), 3.93(6H, s) 5.27-6.02(1H, m), 5.75(1H, s) mp 139.0-142.0.degree. C.5288a 1.33(3H, t, J=7Hz), 1.43(3H, d, J=6Hz), 1.93-2.1(1H, m), 2.57-3.2(2H, m, ), 3.91(6H, s), 4.31(2H, q, J=7Hz), 5.2-6.03(1H, m), 5.68(1H, s)5288b 1.25(3H, t, J=7Hz), 1.45(3H, d, J=6Hz), 1.93-2.14(1H, m), 2.50-3.23(2H, m, ), 3.91(6H, s), 4.27(2H, q, J=7Hz), 5.2-5-98(1H, m), 5.67(1H, s) mp 91.7-94.0.degree. C.5312a 1.48(3H, d, J=6Hz), 2.6-3.62(2H, m), 3.87(6H, s), 5.3-6.07(1H, m), 5.72(1H, s), 7.21(5H, s), 8.37(1H, s) mp 79.1-80.3.degree. C.5312b 1.06(3H, d, J=6Hz), 2.42-3.11(2H, m), 3.38(6H, s), 4.72-5.4(1H, m), 5.23(1H, s), 6.75(5H, s), 7.68(1H, s) mp 112.0-113.5.degree. C.5314a 1.05(3H, t, J=7Hz), 1.43(3H, d, J=6.4Hz), 2.37-3.67(2H, m), 3.93(6H, s), 3.95(2H, q, J=7Hz), 5.22-6.05(1H, m), 5.85(1H, s), 7.18(5H, s) mp 48.0-48.5.degree. C.5314b 1.02(3H, t, J=7Hz), 1.52(3H, d, J=6.4Hz), 3.37-3.5 (2H, m), 3.85(6H, s), 3.98(2H, q, J=7Hz), 5.2 -5.96(1H, m), 5.65(1H, s), 7.16(5H, s) mp 81.4-83.3.degree. C.5520 0.58-1.03(3H, m), 0.98-2.05(4H, m), 3.8(6H, s), 5.37-5.97(1H, m), 5.62(1H, s), 9.2(1H, s) mp 105.0-106.0.degree. C.5523 0.47-1.23(3H, m), 0.47-2.06(4H, m), 1.13(3H, t, J=7Hz), 3.85(6H, s), 4.13(2H, q, J=7Hz), 5.33-6.1(1H, m), 5.63(1H, s)5625 0.75-1.42(6H, m), 1.90-2.57(1H, m), 3.89(6H, s), 5.26-5.9(1H, m), 5.7(1H, s), 7.51(1H, s)5627 0.73-1.47(6H, m), 1.18(3H, t, J=7Hz), 1.93-2.7(1H, m), 3.9(6H, s), 4.15(2H, q, J=7Hz), 5.3-5.91(1H, m), 5.66(1H, s)5651a 1.04(6H, d, J=7Hz), 1.6(3H, d, J=21.8Hz), 1.77-2.43(1H, m), 3.95(6H, s), 5.35-5.97(1H, m), 5.71(1H, s), 10.8(1H, s) mp 103.0-105.0.degree. C.5651b 1.05(6H, d, J=7Hz), 1.66(3H, d, J=21.4Hz), 2.07-2.48(1H, m), 3.88(6H, s), 5.28-5.80(1H, m), 5.67(1H, s), 10.6(1H, s) mp 118.0-121.5.degree. C.5653a 0.65-1.38(6H, m), 1.3(3H, t, J=7Hz), 1.55(3H, d, J=22Hz) 1.9-2.42(1H, m), 3.93(6H, s), 4.23(2H, q, J=7Hz), 5.35-5.93(1H, m) 5.68(1H, s)5653b 1.08(6H, d, J=7Hz), 1.12(3H, t, J=7Hz), 1.63(3H, d, J=21.2Hz) 1.95-2.46(1H, m), 3.94(6H, s), 4.1(2H, q, J=7Hz), 5.3-5.8(1H, m) 5.66(1H, s)5781a 1.77(3H, d, J=21.6Hz), 3.8(6H, s), 5.62(1H, s), 6.27(1H, d, J=21Hz), 7.0-7.67(5H, m) mp 148.0-149.5.degree. C.5781b 1.47(3H, d, J=21Hz), 3.81(6H, s), 6.2(1H, d, J=24.4Hz), 7.16-7.67(5H, m), 10.7(1H, s) mp 113.0-114.0.degree. C.5783a 1.13(3H, t, J=7Hz), 1.74(3H, d, J=21.4Hz), 3.87(6H, s), 4.12(2H, q, J=7Hz), 5.62(1H, s), 6.27(1H, d, J=21.4Hz), 7.07-7.64(5H, m)5783b 1.23(3H, t, J=7Hz), 1.45(3H, d, J=20.8Hz), 3.79(6H, s), 4.23(2H, q, J=7Hz), 5.56(1H, s), 6.15(1H, d, J=24Hz), 7.05-7.62(5H, m) mp 97.6-99.8.degree. C.5833 1.48-1.98(3H, m), 3.88 and 3.92(6H, s), 5.72 and 5.78(1H, s) 8.27(1H, s)5835 1.06-1.44(3H, m), 1.46-2.03(3H, m), 3.94(6H, s), 3.95-4.48(2H, m), 5.77 and 5.79(1H, s), 5.87-6.72(1H, m)5965 1.42(3H, d, J=22.6Hz), 3.53(6H, s), 4.92(2H, s), 5.03-5.7(1H, s), 5.41(1H, s) mp 186.5-189.0.degree. C.5967 1.23(3H, t, J=7Hz), 1.31(3H, t, J=7Hz), 1.79(3H, d, J=21.4Hz), 3.88(6H, s), 4.24(2H, q, J=7Hz), 4.31(2H, q, J=7Hz), 5.03-6.02(1H, m), 5.72(1H, s) mp 63.7-64.8.degree. C.__________________________________________________________________________
TABLE 13__________________________________________________________________________Compound .sup.1 H-NMR(.delta. ppm, CDCl.sub.3)No. and/or Physical data__________________________________________________________________________6001 3.93(6H, s), 4.12-4.36(4H, .m), 5.64-5.69(1H, m), 5.77(1H, s)6002 3.22-4.52(4H, m), 3.81(3H, s), 3.85(6H, s), 5.42-5.94(1H, m), 5.7(1H, s)6082a 1.95-2.43(2H, m), 3.3-4.6(4H, m), 3.88(6H, s), 5.25-5.72(1H, m), 5.67(1H, s), 7.68(1H, s)6082b 1.9-2.4(2H, m), 3.28-4.43(4H, m), 3.87(6H, s), 5.07-5.92(1H, m), 5.68(1H, s), 7.42(1H, s)6084a 1.14(3H, t, J=7.2Hz), 2.01-2.33(2H, m), 3.79-4.32(4H, m), 3.91(6H, S) 4.07(2H, q, J=7.2Hz), 5.61-5.63(1H, m), 5.72(1H, s)6084b 1.19(3H, t, J=7.2Hz), 2.21-2.28(2H, m), 3.6-4.21(4H, m), 3.91(6H, S) 4.05(2H, q, J=7.2Hz), 5.6-5.72(1H, m), 5.71(1H, s)6085b 1, 1(3H, d, J=1.6Hz), 1.2(3H, d, J=1.6Hz), 1.8-2.47(2H, m), 3.3-4.4(4H, m), 3.88(6H, s), 4.75-6.0(2H, m), 5.67(1H, s)6090b 1.87-2.47(2H, m), 3.32-4.27(4H, m), 4.38-4.72(2H, m), 3.90(6H, s), 4.92-6.05(4H, m), 5.68(1H, s)6091b 1.83-2.48(2H, m), 2.25-2.48(1H, m), 3.28-4.43(4H, m), 3.9(6H, s), 4.53- 4.75(2H, m), 5.18-6.0(1H, m), 5.67(1H, s)6136b 2.83-3.8(4H, m), 3.9(6H, s), 5.02-6.04(1H, m), 5.7(1H, s), 8.48(1H, s)6137a 3.15-3.88(4H, m), 3.68(3H, s), 3.91(6H, s), 5.71(1H, s), 5.82-6.1(1H, s)6137b 2.87-4.4(4H, m), 3.69(3H, s), 3.9(6H, s), 5.72(1H, s), 5.28-6.05(1H, s)6216a 2.12-3.73(6H, m), 3.85(6H, s), 5.23-5.77(1H, m), 5.65(1H, s), 6.77(1H, s)6217a 2.34-3.7(6H, m), 3.67(3H, s), 3.9(6H, s), 5.59-5.62(1H, m), 5.72(1H, s)6217b 2.26-3.7(6H, m), 3.78(3H, s), 3.92(6H, s), 5.49-5.57(1H, m), 5.72(1H, s)6459a 1.83-2.34(2H, m), 2.67-4.77(4H, m), 3.72(3H, s), 3.9(6H, s), 5.35-5.8(1H, m), 5.72(1H, s)6459b 1.67-2.34(2H, m), 2.45-4.93(4H, m), 3.67(3H, s), 3.88(6H, s), 5.08-5.9(1H, m), 5.69(1H, s), 9.3(1H, s)6460a 1.78-2.29(2H, m), 3.0-4.67(4H, m), 3.63(3H, s), 3.7(3H, s), 3.88(6H, s) 5.4-5.77(1H, m), 5.68(1H, s)6460b 1.73-2.35(2H, m), 2.67-4.77(4H, m), 3.72(3H, s), 3.72(3H, s), 3.9(6H, s) 5.03-5.9(1H, m), 5.68(1H, s)7004 1.23(3H, t, J=7Hz), 1.58-2.62(6H, m), 3.83(6H, s), 4.17(2H, q, J=7Hz), 5.69(1H, s), 5.82-6.06(1H, m)__________________________________________________________________________
TABLE 14__________________________________________________________________________ ##STR28##CompoundNo. n X W' Y V Remarks__________________________________________________________________________ 1 0 F O OH H 2a 0 F O OCH.sub.3 H cis 2b 0 F O OCH.sub.3 H trans 3a 0 F O OCH.sub.3 COCH.sub.3 cis 3b 0 F O OCH.sub.3 COCH.sub.3 trans 4a 0 F O OCH.sub.3 COPh cis 4b 0 F O OCH.sub.3 COPh trans 5a 0 F O OCH.sub.3 Ms cis 5b 0 F O OCH.sub.3 Ms trans 6a 0 F O OCH.sub.3 Ts cis 6b 0 F O OCH.sub.3 Ts trans 7 0 F O OC.sub.2 H.sub.5 H 8 0 F O OC.sub.2 H.sub. 5 COCH.sub.3 9 0 F O OC.sub.2 H.sub.5 COPh 10 0 F O OC.sub.2 H.sub.5 Ms 11 0 F O OC.sub.2 H.sub.5 Ts 12a 0 F O OH CH.sub.3 cis 12b 0 F O OH CH.sub.3 trans 13a 0 F O OCH.sub.3 CH.sub.3 cis 13b 0 F O OCH.sub.3 CH.sub.3 trans 14 0 F O OC.sub.2 H.sub.5 CH.sub.3 15 0 F O O-n-C.sub.3 H.sub.7 CH.sub.3 16 0 F O O-i-C.sub.3 H.sub.7 CH.sub.3 17 0 F O O-n-C.sub.4 H.sub.9 CH.sub.3 18 0 F O O-i-C.sub.4 H.sub.9 CH.sub.3 19 0 F O O-s-C.sub.4 H.sub.9 CH.sub.3 20a 0 F O O-t-C.sub.4 H.sub.9 CH.sub.3 cis 20b 0 F O O-t-C.sub.4 H.sub.9 CH.sub.3 trans 21 0 F O NH.sub.2 CH.sub.3 22 0 F O NHCH.sub.3 CH.sub.3 23a 0 F O NHC.sub.2 H.sub.5 CH.sub.3 cis 23b 0 F O NHC.sub.2 H.sub.5 CH.sub.3 trans 24 0 F O NH-n-C.sub.3 H.sub.7 CH.sub.3 25 0 F O NH-i-C.sub.3 H.sub.7 CH.sub.3 26 0 F O NH-n-C.sub.4 H.sub.9 CH.sub.3 27 0 F O NH-i-C.sub.4 H.sub.9 CH.sub.3 28 0 F O NH-s-C.sub.4 H.sub.9 CH.sub.3 29a 0 F O NH-t-C.sub.4 H.sub.9 CH.sub.3 cis 29b 0 F O NH-t-C.sub.4 H.sub.9 CH.sub.3 trans 30a 0 F O N(CH.sub.3).sub.2 CH.sub.3 cis 30b 0 F O N(CH.sub.3).sub.2 CH.sub.3 trans 31 0 F O SCH.sub.3 CH.sub.3 32a 0 F O SC.sub.2 H.sub.5 CH.sub.3 cis 32b 0 F O SC.sub.2 H.sub.5 CH.sub.3 trans 33 0 F O S-n-C.sub.3 H.sub.7 CH.sub.3 34 0 F O S-i-C.sub.3 H.sub.7 CH.sub.3 35 0 F O S-n-C.sub.4 H.sub.9 CH.sub.3 36 0 F O S-i-C.sub.4 H.sub.9 CH.sub.3 37 0 F O S-s-C.sub.4 H.sub.9 CH.sub.3 38a 0 F O S-t-C.sub.4 H.sub.9 CH.sub.3 cis 38b 0 F O S-t-C.sub.4 H.sub.9 CH.sub.3 trans 39a 0 F O OH CH.sub.2 Ph cis 39b 0 F O OH CH.sub.2 Ph trans 40a 0 F O OCH.sub.3 CH.sub.2 Ph cis 40b 0 F O OCH.sub.3 CH.sub.2 Ph trans 41 0 F O OC.sub.2 H.sub.5 CH.sub.2 Ph 42 0 F O O-n-C.sub.3 H.sub.7 CH.sub.2 Ph 43 0 F O O-i-C.sub.3 H.sub.7 CH.sub.2 Ph 44 0 F O O-n-C.sub.4 H.sub.9 CH.sub.2 Ph 45 0 F O O-i-C.sub.4 H.sub.9 CH.sub.2 Ph 46 0 F O O-s-C.sub.4 H.sub.9 CH.sub.2 Ph 47 0 F O O-t-C.sub.4 H.sub.9 CH.sub.2 Ph 48a 0 F O OCH.sub.2 Ph CH.sub.2 Ph cis 48b 0 F O OCH.sub.2 Ph CH.sub.2 Ph trans 49 0 F O NH.sub.2 CH.sub.2 Ph 50 0 F O NHCH.sub.3 CH.sub.2 Ph 51 0 F O NHC.sub.2 H.sub.5 CH.sub.2 Ph 52 0 F O NH-n-C.sub.3 H.sub.7 CH.sub.2 Ph 53 0 F O NH-i-C.sub.3 H.sub.7 CH.sub.2 Ph 54 0 F O NH-n-C.sub.4 H.sub.9 CH.sub.2 Ph 55 0 F O NH-i-C.sub.4 H.sub.9 CH.sub.2 Ph 56 0 F O NH-s-C.sub.4 H.sub.9 CH.sub.2 Ph 57 0 F O NH-t-C.sub.4 H.sub.9 CH.sub.2 Ph 58 0 F O N(CH.sub.3).sub.2 CH.sub.2 Ph 59 0 F O SCH.sub.3 CH.sub.2 Ph 60 0 F O SC.sub.2 H.sub.5 CH.sub.2 Ph 61 0 F O S-n-C.sub.3 H.sub.7 CH.sub.2 Ph 62 0 F O S-i-C.sub.3 H.sub.7 CH.sub.2 Ph 63 0 F O S-n-C.sub.4 H.sub.9 CH.sub.2 Ph 64 0 F O S-i-C.sub.4 H.sub.9 CH.sub.2 Ph 65 0 F O S-s-C.sub.4 H.sub.9 CH.sub.2 Ph 66 0 F O S-t-C.sub.4 H.sub.9 CH.sub.2 Ph 67 1 F O OH H 68 1 F O OCH.sub.3 H 69 1 F O OCH.sub.3 COCH.sub.3 70 1 F O OCH.sub.3 COPh 71 1 F O OCH.sub.3 Ms 72 1 F O OCH.sub.3 Ts 73a 1 F O OC.sub.2 H.sub.5 H cis 73b 1 F O OC.sub.2 H.sub.5 H trans 74a 1 F O OC.sub.2 H.sub.5 COCH.sub.3 cis 74b 1 F O OC.sub.2 H.sub.5 COCH.sub.3 trans 75a 1 F O OC.sub.2 H.sub.5 COPh cis 75b 1 F O OC.sub.2 H.sub.5 COPh trans 76a 1 F O OC.sub.2 H.sub.5 Ms cis 76b 1 F O OC.sub.2 H.sub.5 Ms trans 77a 1 F O OC.sub.2 H.sub.5 Ts cis 77b 1 F O OC.sub.2 H.sub.5 Ts trans 78 1 F O OH CH.sub.3 79 1 F O OCH.sub.3 CH.sub.3 80a 1 F O OC.sub.2 H.sub.5 CH.sub.3 cis 80b 1 F O OC.sub.3 H.sub.5 CH.sub.3 trans 81 1 F O O-n-C.sub.3 H.sub.7 CH.sub.3 82 1 F O O-i-C.sub.3 H.sub.7 CH.sub.3 83 1 F O O-n-C.sub.4 H.sub.9 CH.sub.3 84 1 F O O-i-C.sub.4 H.sub.9 CH.sub.3 85 1 F O O-s-C.sub.4 H.sub.9 CH.sub.3 86 1 F O O-t-C.sub.4 H.sub.9 CH.sub.3 87 1 F O NH.sub.2 CH.sub.3 88 1 F O NHCH.sub.3 CH.sub.3 89 1 F O NHC.sub.2 H.sub.5 CH.sub.3 90 1 F O NH-n-C.sub.3 H.sub.7 CH.sub.3 91 1 F O NH-i-C.sub.3 H.sub.7 CH.sub.3 92 1 F O NH-n-C.sub.4 H.sub.9 CH.sub.3 93 1 F O NH-i-C.sub.4 H.sub.9 CH.sub.3 94 1 F O NH-s-C.sub.4 H.sub.9 CH.sub.3 95 1 F O NH-t-C.sub.4 H.sub.9 CH.sub.3 96 1 F O N(CH.sub.3).sub.2 CH.sub.3 97 1 F O SCH.sub.3 CH.sub.3 98 1 F O SC.sub.2 H.sub.5 CH.sub.3 99 1 F O S-n-C.sub.3 H.sub.7 CH.sub.3100 1 F O S-i-C.sub.3 H.sub.7 CH.sub.3101 1 F O S-n-C.sub.4 H.sub.9 CH.sub.3102 1 F O S-i-C.sub.4 H.sub.9 CH.sub.3103 1 F O S-s-C.sub.4 H.sub.9 CH.sub.3104 1 F O S-t-C.sub.4 H.sub.9 CH.sub.3105a 1 F O OH CH.sub.2 Ph cis105b 1 F O OH CH.sub.2 Ph trans106 1 F O OCH.sub.3 CH.sub.2 Ph107a 1 F O OC.sub.2 H.sub.5 CH.sub.2 Ph cis107b 1 F O OC.sub.2 H.sub.5 CH.sub.2 Ph trans108 1 F O O-n-C.sub.3 H.sub.7 CH.sub.2 Ph109 1 F O O-i-C.sub.3 H.sub.7 CH.sub.2 Ph110 1 F O O-n-C.sub.4 H.sub.9 CH.sub.2 Ph111 1 F O O-i-C.sub.4 H.sub.9 CH.sub.2 Ph112 1 F O O-s-C.sub.4 H.sub.9 CH.sub.2 Ph113 1 F O O-t-C.sub.4 H.sub.9 CH.sub.2 Ph114 1 F O O CH.sub.2 Ph CH.sub.2 Ph115 1 F O NH.sub.2 CH.sub.2 Ph116 1 F O NHCH.sub.3 CH.sub.2 Ph117a 1 F O NHC.sub.2 H.sub.5 CH.sub.2 Ph cis117b 1 F O NHC.sub.2 H.sub.5 CH.sub.2 Ph trans118 1 F O NH-n-C.sub.3 H.sub.7 CH.sub.2 Ph119 1 F O NH-i-C.sub.3 H.sub.7 CH.sub.2 Ph120 1 F O NH-n-C.sub.4 H.sub.9 CH.sub.2 Ph121 1 F O NH-i-C.sub.4 H.sub.9 CH.sub.2 Ph122 1 F O NH-s-C.sub.4 H.sub.9 CH.sub.2 Ph123a 1 F O NH-t-C.sub.4 H.sub.9 CH.sub.2 Ph cis123b 1 F O NH-t-C.sub.4 H.sub.9 CH.sub.2 Ph trans124 1 F O N(CH.sub.3).sub.2 CH.sub.2 Ph125 1 F O SCH.sub.3 CH.sub.2 Ph126 1 F O SC.sub.2 H.sub.5 CH.sub.2 Ph127 1 F O S-n-C.sub.3 H.sub.7 CH.sub.2 Ph128 1 F O S-i-C.sub.3 H.sub.7 CH.sub.2 Ph129 1 F O S-n-C.sub.4 H.sub.9 CH.sub.2 Ph130 1 F O S-i-C.sub.4 H.sub.9 CH.sub.2 Ph131 1 F O S-s-C.sub.4 H.sub.9 CH.sub.2 Ph132 1 F O S-t-C.sub.4 H.sub.9 CH.sub.2 Ph133 2 F O OH H134a 2 F O OCH.sub.3 H cis134b 2 F O OCH.sub.3 H trans135 2 F O OCH.sub.3 COCH.sub.3136 2 F O OCH.sub.3 COPh137 2 F O OCH.sub.3 Ms138 2 F O OCH.sub.3 Ts139 2 F O OC.sub.2 H.sub.5 H140 2 F O OC.sub.2 H.sub.5 COCH.sub.3141 2 F O OC.sub.2 H.sub.5 COPh142 2 F O OC.sub.2 H.sub.5 Ms143 2 F O OC.sub.2 H.sub.5 Ts144 2 F O OH CH.sub.2 Ph145 2 F O OCH.sub.3 CH.sub.2 Ph146 2 F O OC.sub.2 H.sub.5 CH.sub.2 Ph147 3 F O OH H148 3 F O OCH.sub.3 H149 3 F O OCH.sub.3 COCH.sub.3150 3 F O OCH.sub.3 COPh151 3 F O OCH.sub.3 Ms152 3 F O OCH.sub.3 Ts153 3 F O OC.sub.2 H.sub.5 H154 3 F O OC.sub.2 H.sub.5 COCH.sub.3155 3 F O OC.sub.2 H.sub.5 COPh156 3 F O OC.sub.2 H.sub.5 Ms157 3 F O OC.sub.2 H.sub.5 Ts158 3 F O OH CH.sub.2 Ph159 3 F O OCH.sub.3 CH.sub.2 Ph160 3 F O OC.sub.2 H.sub.5 CH.sub.2 Ph161 0 F S OH H162 0 F S OCH.sub.3 H163 1 F S OH H164 1 F S OCH.sub.3 H165 0 Cl O OH H166 0 Cl O OC.sub.2 H.sub.5 H167 1 Cl O OH H168 1 Cl O OC.sub.2 H.sub.5 H169 1 Br O OC.sub.2 H.sub.5 H__________________________________________________________________________
TABLE 15__________________________________________________________________________ ##STR29##CompoundNo. R.sup.3' R.sup.4' X Y W' V__________________________________________________________________________201 CH(CH.sub.3)(CH.sub.2).sub.2 F OH O H202 CH(CH.sub.3)(CH.sub.2).sub.2 F OC.sub.2 H.sub.5 O H203 C(CH.sub.3).sub.2(CH.sub.2).sub.2 F OH O H204 C(CH.sub.3).sub.2(CH.sub.2).sub.2 F OC.sub.2 H.sub.5 O H205 (CH.sub.2).sub.2C(CH.sub.3).sub.2 F OH O H206 (CH.sub.2).sub.2C(CH.sub.3).sub.2 F OC.sub.2 H.sub.5 O H207 (CH.sub.2).sub.2CH(CH.sub.3)CH.sub.2 F OH O H208 (CH.sub.2).sub.2CH(CH.sub.3)CH.sub. 2 F OC.sub.2 H.sub.5 O H209 (CH.sub.2).sub.2CH(t-C.sub.4 H.sub.9)CH.sub.2 F OH O H210 (CH.sub.2).sub.2CH(t-C.sub.4 H.sub.9)CH.sub.2 F OC.sub.2 H.sub.5 O H211 C(CH.sub.3).sub.2(CH.sub.2).sub.3 F OH O H212 C(CH.sub.3).sub.2(CH.sub.2).sub.3 F OC.sub.2 H.sub.5 O H213 (CH.sub.2).sub.3C(CH.sub.3).sub.2 F OH O H214 (CH.sub.2).sub.3C(CH.sub.3).sub.2 F OC.sub.2 H.sub.5 O H215 (CH.sub.2).sub.3CH(OH) F OH O H216 (CH.sub.2).sub.3CH(OH) F OC.sub.2 H.sub.5 O H217 (CH.sub.2).sub.3CH(OCH.sub.3) F OH O H218 (CH.sub.2).sub.3CH(OCH.sub.3) F OC.sub.2 H.sub.5 O H219 (CH.sub.2).sub.3C(O) F OH O H220 (CH.sub.2).sub.3C(O) F OC.sub.2 H.sub.5 O H221 (CH.sub.2).sub.2CH(OH)CH.sub.2 F OH O H222 (CH.sub.2).sub.2CH(OH)CH.sub.2 F OC.sub.2 H.sub.5 O H223 (CH.sub.2).sub.2CH(OCH.sub.3)CH.sub.2 F OH O H224 (CH.sub.2).sub.2CH(OCH.sub.3)CH.sub.2 F OC.sub.2 H.sub.5 O H225 (CH.sub.2).sub.2C(O)CH.sub.2 F OH O H226 (CH.sub.2).sub.2C(O)CH.sub.2 F OC.sub.2 H.sub.5 O H227 (CH.sub.2).sub.2O F OH O H228 (CH.sub.2).sub.2O F OCH.sub.3 O H229 (CH.sub.2).sub.2S F OH O H230 (CH.sub.2).sub.2S F OCH.sub.3 O H231 CH.sub.2OCH.sub.2 F OH O H232 CH.sub.2OCH.sub.2 F OCH.sub.3 O H233 CH.sub.2SCH.sub.2 F OH O H234 CH.sub. 2SCH.sub.2 F OCH.sub.3 O H235 (CH.sub.2).sub.3O F OH O H236 (CH.sub.2).sub.3O F OC.sub.2 H.sub.5 O H237 (CH.sub.2).sub.3S F OH O H238 (CH.sub.2).sub.3S F OC.sub.2 H.sub.5 O H239 (CH.sub.2).sub.3N(CO.sub.2 CH.sub.3) F OH O H240 (CH.sub.2).sub.3N(CO.sub.2 CH.sub.3) F OC.sub.2 H.sub.5 O H241 (CH.sub.2).sub.2OCH.sub.2 F OH O H242 (CH.sub.2).sub.2OCH.sub.2 F OC.sub.2 H.sub.5 O H243 (CH.sub.2).sub.2SCH.sub.2 F OH O H244 (CH.sub.2).sub.2SCH.sub.2 F OCH.sub.3 O H245 (CH.sub.2).sub.2N(CO.sub.2 CH.sub.3)CH.sub.2 F OH O H246 (CH.sub.2).sub.2N(CO.sub.2 CH.sub.3)CH.sub.2 F OCH.sub.3 O H247 CH.sub.2O(CH.sub.2).sub.2 F OH O H248 CH.sub.2O(CH.sub.2).sub.2 F OC.sub.2 H.sub.5 O H249 CH.sub.2S(CH.sub.2).sub.2 F OH O H250 CH.sub.2S(CH.sub.2).sub.2 F OC.sub.2 H.sub.5 O H251 CH.sub.2N(CO.sub.2 CH.sub.3)(CH.sub.2).sub.2 F OH O H252 CH.sub.2N(CO.sub.2 CH.sub.3)(CH.sub.2).sub.2 F OC.sub.2 H.sub.5 O H__________________________________________________________________________
TABLE 16______________________________________Com-poundNo. .sup.1 H-NMR (.delta. ppm, CDCl.sub.3) and/or physical______________________________________ data2a 1.33-3.03(6H, m), 3.82(3H, s), 4.07-4.60(1H, m) Mass/m/Z=162 (M.sup.+)2b 1.30-2.90(6H, m), 3.80(3H, s), 4.03-4.63(1H, m)3a 1.50-2.93(6H, m), 2.02(3H, s), 3.77(3H, s), 5.00-5.50(1H, m), Mass/m/Z=204(M.sup.+)3b 1.37-2.73(6H, m), 2.03(3H, s), 3.77(3H, s), 4.80-5.47(1H, m), Mass/m/Z=204(M.sup.+)4a 1.47-3.03(6H, m)3, 73(3H, s), 5.20-5.73(1H, m), 7.20-8.22(5H, m)4b 1.37-2.77(6H, m), 3.80(3H, s), 5.03-5.77(1H, m), 7.22-8.25(5H, m)5a 1.52-2.63(6H, m), 3.00(3H, s), 3.81(3H, s), 4.80-5.28(1H, m)5b 1.38-2.63(6H, m), 3.01(3H, s), 3.82(3H, s) 4.63-5.47(1H, m)6a 1.37-2.37(6H, m), 2.46(3H, s), 3.70(3H, s) 4.27-5.17(1H, m), 7.00-8, 20(5H, m)6b 1.30-2.37(6H, m), 2.43(3H, s), 3.63(3H, s), 3.93-5.00(1H, m), 6.93-7.93(5H, m)12a 1.43-2.80(6H, m), 3.40(3H, s), 3.63-4.57(1H, m) 8.90(1H, s)12b 1.43-2.60(6H, m), 3.43(3H, s), 3.77-4.67(1H, m) 8.47(1H, s)13a 1.50-2.82(6H, m), 3.31(3H, s), 3.80(3H, s) 3.90-4.55(1H, m), Mass/m/Z= 176(M.sup.+)13b 1.42-2.68(6H, m), 3.35(3H, s), 3.80(3H, s), 4.03-5.00(1H, m)20a 1.47-2.80(6H, m), 1.53(9H, s), 3.37(3H, s), 3.57-4.37(1H, m)23b 1.17(3H, t, J=6.6Hz), 1.50-2.70(6H, m), 3.36(2H, q, J=6.6Hz), 3.37(3H, s), 3.72-4.53(1H, m)29a 1.43-2.57(6H, m), 1.39(9H, s), 3.37(3H, s), 3.83-4.28(1H, m), Mass/m/Z=217(M.sup.+)29b Mass/m/Z=217(M.sup.+)30a Mass/m/Z=189(M.sup.+)30b 1.43-2.60(6H, m), 2.60-3.12(6H, m), 3.39(3H, s), 3.93-4.57(1H, m), Mass/m/Z=189(M.sup.+)32a 1.33-2.62(6H, m), 1.28(3H, t, J=7.0Hz), 2.93(2H, q, J=7.0Hz), 3.35(3H, s), 3.57-4.30(1H, m), Mass/m/Z=206(M.sup.+)32b Mass/m/Z=206(M.sup.+)38b 1.30-2.60(6H, m), 1.48(9H, s), 3.33(3H, s), 3.42-4.37(1H, m)39a 1.48-2.80(6H, m), 3.80-4.38(1H, m), 4.58(2H, s), 7.25(5H, s), 7.87(1H, s)39b 1.50-2.65(6H, m), 4.00-4.47(1H, m), 4.57(2H, s), 7.33(5H, s), 7.55(1H, s)40a 1.57-2.87(6H, m), 3.75(3H, s), 3.90-4.40(1H, m), 4.45(2H, s), 7.23(5H, s)40b 1.59-2.43(6H, m), 3.75(3H, s), 3.77-4.43(1H, M), 4.50(2H, s), 7.25(5H, s), Mass/m/Z=252(M.sup.+)48b 1.47-2.57(6H, m), 4.40(2H, s), 5.18(2H, s), 7.20(5H, s), 7.29(5H, s)73a 1.33(3H, t, J=7Hz), 1, 10-2.50(8H, m), 2.83-3.17(1H, bs), 3.67-4.17(1H, m), 4.23(2H, q, J=7Hz), Mass/m/Z=190(m.sup.+)73b Mass/m/Z=190(M.sup.+)74a 1.28(3H, t, J=7Hz), 1.33-2.13(8H, m), 2.03(3H, s), 4.20(2H, q, J=7Hz), 4.87-5.32(1H, m)74b 1.27(3H, t, J=7Hz), 1.17-2.23(8H, m), 2.02(3H, s), 4.18(2H, q, J=7Hz), 4.70-5.30(1H, m)75a 1.18(3H, t, J=7Hz), 1.37-2.28(8H, m), 4.17(2H, q, J=7Hz), 5.13-5.57(1H, m), 7.17-7.70(3H, m), 7.80-8.23(2H, m), Mass/m/Z=294(M.sup.+)75b 1.12(3H, t.J=7Hz), 1.18-2.38(8H, m), 4.12(2H, q, J=7Hz), 4.85-5.62(1H, m), 7.07-7.62((3H, m), 7.70-8.20(2H, m), Mass/m/Z=294(M.sup.+)76a 1.32(3H, t, J=7Hz), 1.28-2.52(8H, m), 3.00(3H, s), 4.25(2, t, J=7Hz), 4.48-5.05(1H, m)76b 1.30(3H, t, J=7Hz), 1.30-2.33(8H, m), 2.95(3H, s), 4.23(2H, q, J=7Hz), 4.53-5.37(1H, m)77a 1.23(3H, t, J=7Hz), 1.18-2.22(8H, m), 2.42(3H, s), 4.08(2H, q, J=7Hz), 4.50-4.93(1H, m), 6.90-7.37(2H, m), 7.56-7.88(2H, m), Mass/m/Z=344(M.sup.+)77b 1.22(3H, t, J=7Hz), 1.20-2.33(8H, m), 2.40(3H, m), 4.03(2H, q, J=7Hz), 4.50-5.30(1H, m), 6.95-7.37(2H, m), 7.53-7.83(2H, m), Mass/m/Z=344(M.sup.+)80a Mass/m/Z=204(M.sup.+)80b Mass/m/Z=204(M.sup.+)105a 0.80-2.85(8H, m), 3.28-4.12(iH, m), 4.60(1H, s), 7.27(5H, s)107b 1.25(3H, t, J=7Hz), 1.23-2.30(8H, m), 3.23-4.00(1H, m), 4.18(2H, q, J=7Hz), 4.43(1H, q, J=12Hz), 4.60(1H, q, J=12Hz, ), 7.23(5H, s)117a 1.10(3H, t, J=7Hz), O.72-2.45(8H, m), 2.95-4.00(3H, m), 4.60(2H, s), 6.08-6.77(1, bs), 7.27(5H, s)123a 0.88-2.50(8H, m), 1.32(9H, s), 3.23-3.97(1H, m), 4.60(2H, s), 5.93-6.53(1H, bs), 7.27(5H, s)134a 0.98-2.62(10H, m), 3.80(3H, s), 3.88-4.35(1H,m)134b 1.18-2.75(10H, m), 3.78(3H, s), 3.90-4.40(1H, m)153 1.35-2.87(12H, m), 1.30(3H, t, J=7.0Hz), 3.80-4.40(1H, m), 4.25(2H,q, J=7.0Hz)164 Mass/m/Z=192(M.sup.+)168 0.84-3.02(8H, m), 1.3(3H, t, J=7Hz), 3.25-4.48(1H.m), 4.25(2H, q, J=7Hz242 1.3(3H, t.J=7Hz), 1.5-217(2H, m), 2.17, 2.67(1H, m), 3.22-4.53(5H, m) 4.24(2H, q, J=7Hz)ppm______________________________________
Process for synthesis of compound represented by the formula (II) ##STR30## (wherein R.sup.3', R.sup.4', X, A and Y are as defined hereinbefore, and W' represents an oxygen atom or sulfur atom).
In the above reaction formula of the Process B-1, a compound represented by the formula (II-a) can be prepared by reacting a halogenated ketone derivative or halogenated thione derivative of the formula (IV) with a reducing agent without any solvents or in the presence of a suitable solvent in the temperature range of -78.degree. C. to the boiling point of the solvent for 1 to 24 hours using a suitable base.
When a solvent is used in this reaction, examples thereof include, for example, alcoholic solvents such as methanol, ethanol and isopropyl alcohol, hydrocarbonic solvents such as benzene, toluene and xylene, halogenated hydrocarbonic solvents such as dichloromethane and chloroform, etherial solvents such as diethyl ether, diisopropyl ether, tetrahydrofuran and 1,4-dioxane, ketonic solvents such as acetone and methyl ethyl ketone, ester solvents such as methyl acetate and ethyl acetate, aprotic polar solvents such as dimethylformamide, dimethylsulfoxide and dimethylacetamide, acetonitrile, water, etc.
Further, examples of the reducing agent include organotin compounds such as triphenyltin hydride, diphenyltin hydride, tri-n-butyltin hydride and di-nbutyltin hydride metal hydrogen complexes and their related compounds such as lithium tri-tert-butylaluminum hydride, sodium borohydride, sodium trimethoxyborohydride, sodium borohydride sulfur, sodium cyanoborohydride, lithium borohydride, calcium triethylborohydride, potassium borohydride, potassium triisopropoxy borohydride, potassium tri-sec-butylborohydride, zinc borohydride, tetramethylammonium borohydride and tetran-butylammonium cyanoborohydride, diborane and borane complexes such as a dimethylamine-borane complex, a trimethylamine-borane borane complex, a triethylamineborane complex, a tert-butylamine-borane complex, a pyridine-borane complex, a dimethylsulfide-borane complex, a morpholine-borane complex and a 1,4-oxathiane-borane complex, aklylborances such as dicylohexylborane and 9-boradicyclo[3,3,1]nonane, metal alkoxides such as aluminum isopropoxide and aluminum tert-butoxide, catalytically hydrogenating catalysts such as palladium carbon, platinum oxide and Raney nickel, etc. ##STR31## (wherein R.sup.3', R.sup.4', R.sup.5, X, A and Y are as defined hereinbefore, and W' represents an oxygen atom or sulfur atom, V' has the same meaning as the above V but a hydrogen atom is excluded, and X' represents a halogen atom).
In the above reaction formula of the Process B-2, a compound represented by the formula (II-c) can be prepared by reacting a halogenated alcohol or thiol derivative of the formula (II-b) with a compound represented by V'-X' without any solvents or in the presence of a suitable solvent in the temperature range of -78.degree. C. to the boiling point of the solvent for 1 to 24 hours using a suitable base.
When a solvent is used in this reaction, examples thereof include, for example, hydrocarbonic solvents such as benzene, toluene and xylene, halogenated hydrocarbonic solvents such as dichloromethane and chloroform, etherial solvents such as diethyl ether, diisopropyl ether, tetrahydrofuran and 1,4-dioxane, ketonic solvents such as acetone and methyl ethyl ketone, ester solvents such as methyl acetate and ethyl acetate, aprotic polar solvents such as dimethylformamide, dimethylsulfoxide and dimethylacetamide, acetonitrile, water, etc.
Further, examples of the base include carbonates such as sodium carbonate and potassium carbonate, metal hydroxides such as sodium hydroxide and potassium hydroxide, metal alcoholates such as sodium methylate and sodium ethylate, alkali metal hydrides such as sodium hydride and potassium hydride, and lithium amides such as lithium diethylaminde, lithium diisopropylamide and lithium bis(trimethylsilyl)amide ##STR32## (wherein R.sup.3', R.sup.4', R.sup.5, X, Y and V' are as defined hereinbefore, W' represents an oxygen atom or sulfur atom and M represents a cation of an alkyl metal or alkaline earth metal).
In the above reaction formula of the Process B-3, a compound represented by the formula (II-d) can be prepared by reacting a compound represented by the formula (II-f) with a suitable base in the presence of a suitable solvent in the temperature range of room temperature to the boiling point of the solvent for 1 to 24 hours. Further, a compound represented by the formula (II-e) can be prepared by treating a compound represented by the formula (II-d) with an acid. Examples of the solvent use in this reaction include alcoholic solvents such as methanol, ethanol and isopropyl alcohol, hydrocarbonic solvents such as benzene, toluene and xylene, halogenated hydrocarbonic solvents such as dichloromethane and chloroform, etherial solvents such as diethyl ether, diisopropyl ether, tetrahydrofuran and 1,4-dioxane, ketonic solvents such as acetone and methyl ethyl ketone, ester solvents such as methyl acetate and ethyl acetate, aprotic polar solvents such as dimethylformamide, dimethylsulfoxide and dimethylacetamide, acetonitrile, water, etc. Further, examples of the base include carbonate salts such as sodium carbonate, potassium carbonate, sodium bicarbonate and potassium bicarbonate, metal hydroxides such as sodium hydroxide and potassium hydroxide, metal alcoholates such as sodium methylate and sodium ethylate, alkali metal hydrides such as sodium hydride and potassium hydride. ##STR33## (wherein R.sup.3', R.sup.4', R.sup.5, X, Y and V' are as defined hereinbefore, and W' represents an oxygen atom or sulfur atom, R' represents a group which is allowed to convert to Y through this reaction and T represents a hydroxyl group, mercapto group, amino group or halogen atom).
In the above reaction formula of the Process B-4, a compound represented by the formula (II-f) can be prepared by reacting a carboxylic acid of the formula (II-e) with a suitable alkyl halide, alcohol mercaptane or amine (R-T) without any solvents or in the presence of a suitable solvent in the temperature range of under ice cooling to the boiling point of the solvent for 1 to 24 hours using a suitable condensing agent. Examples of the solvent use in this reaction include hydrocarbonic solvents such as benzene, toluene and xylene, halogenated hydrocarbonic solvents such as dichloromethane and chloroform, etherial solvents such as diethyl ether, diisopropyl ether, tetrahydrofuran and 1,4-dioxane, ketonic solvents such as acetone and methyl ethyl ketone, ester solvents such as methyl acetate and ethyl acetate, aprotic polar solvents such as dimethylformamide, dimethylsulfoxide and dimethylacetamide, acetonitrile, water, etc.
Further, examples of the condensing agent include, carbonate salts such as sodium carbonate, potassium carbonate, sodium bicarbonate and potassium bicarbonate, metal hydroxides such as sodium hydroxide and potassium hydroxide, metal alcoholates such as sodium methylate and sodium ethylate, alkali metal hydrides such as sodium hydride and potassium hydride, organic bases such as diazabicycloundecene, and dehydrating agents such as dicyclohexylcarbodiimide. ##STR34## (wherein R.sup.3', R.sup.4', R.sup.5, X, Y and V' are as defined hereinbefore, and W' represents an oxygen atom or sulfur atom, and V" represents a lower alkoxycarbonyl group, lower alkylsulfonyl group, or optionally substituted arylsulfonyl group).
In the above reaction formula of the Process B-5, a compound represented by the formula (II-f) can be prepared by reacting a carboxylic acid of the formula (II-e) with a suitable activating agent represented by V"-Cl to give an active intermediate and reacting the intermediate with a corresponding alcohol, amine or thiol in the absence or presence of a catalyst. Examples of the solvent use in the reaction include hydrocarbonic solvents such as benzene, toluene and xylene, halogenated hydrocarbonic solvents such as dichloromethane and chloroform, etherial solvents such as diethyl ether, diisopropyl ether, tetrahydrofuran and 1,4-dioxane, ketonic solvents such as acetone and methyl ethyl ketone, ester solvents such as methyl acetate and ethyl acetate, aprotic polar solvents such as dimethylformamide, dimethylsulfoxide and dimethylacetamide, acetonitrile, water, etc. Examples of the base include organic bases such as pyridine and triethylamine, and examples of the activating agent include alkyl chloroformates such as methyl chloroformate and ethyl chloroformate, arylsulfonyl chloride such as benzenesulfonyl chloride and toluenesulfonyl chloride, etc. Examples of the catalyst include dimethylaminopyridine, 4-pyrrolidinopyridine, etc.
Process for the synthesis of compound represented by the formula (I) ##STR35## (wherein X, A, W, Y, R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, Z.sup.1 and Z.sup.2 are as defined hereinbefore, and U represents a halogen atom, lower alkylsulfonyl group or arylalkylsulfonyl group).
In the above reaction formula of the process A-1, a compound represented by the formula (I') can be prepared by reacting a halogenated alcohol, halogenated thiol or halogenated enethiol derivative of the formula (II) with a substituted pyrimidine or triazine of the formula (III) without any solvents or in the presence of a suitable solvent in the temperature range of -78.degree. C. to the boiling point of the solvent for 1 to 24 hours using a suitable base.
When a solvent is used in this reaction, examples thereof include, for example, hydrocarbonic solvents such as benzene, toluene and xylene, halogenated hydrocarbonic solvents such as dichloromethane and chloroform, etherial solvents such as diethyl ether, diisopropyl ether, tetrahydrofuran and 1,4-dioxane, ketonic solvents such as acetone and methyl ethyl ketone, ester solvents such as methyl acetate and ethyl acetate, aprotic polar solvents such as dimethylformamide, dimethylsulfoxide and dimethylacetamide, acetonitrile, water, etc.
Further, examples of the base include carbonate salts such as sodium carbonate and potassium carbonate, metal hydroxides such as sodium hydroxide and potassium hydroxide, metal alcoholates such as sodium methylate and sodium ethylate, alkali metal hydrides such as sodium hydride and potassium hydride, and lithium amides such as lithium diethylamide, lithium diisopropylamide and lithium bis(trimethylsilyl)amide. ##STR36## wherein X, A, W, Y, R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, Z.sup.1 and Z.sup.2 are as defined hereinbefore, Y.sup.1 represents a lower alkyl, lower alkenyl, lower alkynyl, aryl, aralkyl, lower cycloalkyl, lower cycloalkenyl, pyridyl, furylmethyl, furyl, thienyl or group N ##STR37## (wherein R.sup.6 and R.sup.7 are as defined herein before) each optionally substituted with halogen atom(s), lower alkyl, hydroxyl, lower alkoxy, lower alkythio, lower alkoxycarbonyl, lower alkylcarbonyl, cyano, nitro or azido, and T represents a hydroxyl group, mercapto group or halogen atom].
In the above reaction formula of the Process A-2, a compound represented by the formula (I-b) can be prepared by reacting a carboxylic acid of the formula (I-a) with a compound Y.sup.1 T which has a halogen atom, hydroxyl group or mercapto group in the presence of a suitable condensing agent without any solvents or in the presence of a suitable solvent in the temperature range of under ice cooling to the boiling point of the solvent for 1 to 24 hours. Examples of the solvent used in the reaction include hydrocarbonic solvents such as benzene, toluene and xylene, halogenated hydrocarbonic solvents such as dichloromethane and chloroform, etherial solvents such as diethyl ether, diisopropyl ether, tetrahydrofuran and 1,4-dioxane, ketonic solvents such as acetone and methyl ethyl ketone, ester solvents such as methyl acetate and ethyl acetate, aprotic polar solvents such as dimethylformamide, dimethylsulfoxide and dimethylacetamide, acetonitrile, water, etc. Further, examples of the condensing agent include carbonate salts such as sodium carbonate, potassium carbonate, sodium bicarbonate and potassium bicarbonate, metal hydroxides such as sodium hydroxide and potassium hydroxide, metal alcoholates such as sodium methylate and sodium ethylate, alkali metal hydrides such as sodium hydride and potassium hydride, organic bases such as diazabicycloundecene, and dehydrating and condensing agents such as dicylohexylcarbodiimide. ##STR38## (wherein X, W, Y, R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, Z.sup.1 and Z.sup.2 are as defined hereinbefore, and V represents a lower alkoxycarbony, lower alkylsulfonyl or optionally substituted arylsulfonyl group).
In the above reaction formula of the Process A-3, a compound represented by the formula (I-c) can be prepared by reacting a carboxylic acid of the formula (I-a) with a suitable activating agent represented by V-Cl in the presence of a suitable base to give first an active intermediate and then reacting the intermediate with a corresponding alcohol, amine or thiol in the presence or absence of a catalyst. Examples of the solvent use in the reaction include hydrocarbonic solvents such as benzene, toluene and xylene, halogenated hydrocarbonic solvents such as dichloromethane and chloroform, etherial solvents such as diethyl ether, diisopropyl ether, tetrahydrofuran and 1,4-dioxane, ketonic solvents such as acetone and methyl ethyl ketone, ester solvents such as methyl acetate and ethyl acetate, aprotic polar solvents such as dimethylformamide, dimethylsulfoxide and dimethylacetamide, acetonitrile, water, etc. Examples of the base include organic bases such as pyridine and triethylamine. Examples of the activating agent include alkyl chloroformates such as methyl chloroformate and ethyl chloroformate, and arylsulfonyl chlorides such as benzenesulfonyl chloride and toluenesulfonyl chloride. Examples of the catalyst include dimethylaminopyridine 4-pyrrolidinopyridine, etc. ##STR39## (wherein X, W, Y, R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, Z.sup.1 and Z.sup.2 are as defined hereinbefore, and M represents a cation of an alkali metal or alkaline earth metal).
In the above reaction formula of the Process A-4, a compound represented by the formula (I-f) can be prepared by reacting a compound represented by the formula (I-d) with a suitable base in the presence of a suitable solvent in the temperature range of room temperature to boiling point of the solvent for 1 to 24 hours. Further, a compound represented by the formula (I-a) can be prepared by treating a compound represented by the formula (I-f) with an acid. Examples of the solvent use in the reaction include alcoholic solvents such as methanol, ethanol and isopropyl alcohol, hydrocarbonic solvents such as benzene, toluene and xylene, halogenated hydrocarbonic solvents such as dichloromethane and chloroform, etherial solvents such as diethyl ether, diisopropyl ether, tetrahydrofuran and 1,4-dioxane, ketonic solvents such as acetone and methyl ethyl ketone, ester solvents such as methyl acetate and ethyl acetate, aprotic polar solvents such as dimethylformamide, dimethylsulfoxide and dimethylacetamide, acetonitrile, water, etc. Further, examples of the base include carbonate salts such as sodium carbonate potassium bicarbonate, metal hydroxides such as sodium hydroxide and potassium hydroxide, metal alcoholates such as sodium methylate and sodium ethylate, alkali metal hydrides such as sodium hydride and potassium hydride, etc.
When in the general formula (I) A represents an oxygen atom and Y represents ##STR40## and particularly R.sup.8 represents a hydrogen atom, a substituent R.sup.12 can be introduced by the following process A-5. ##STR41## (wherein X, W, A, Z.sup.1, Z.sup.2, R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.8 and R.sup.9 are as defined hereinbefore, and R.sup.12 represents a lower alkyl group).
In the above reaction formula of the process A-5, a compound represented by the formula (I-h) can be prepared by reacting an amide derivative of the formula (I-g) with an alkylating agent without any solvents or in the presence of a suitable solvent in the temperature range of -78.degree. C. to the boiling point of the solvent for 1 to 48 hours, if necessary using a suitable base.
When a solvent is used in this reaction, examples thereof include, for example, hydrocarbonic solvents such as benzene, toluene and xylene, halogenated hydrocarbonic solvents such as dichloromethane and chloroform, etherial solvents such as diethyl ether, diisopropyl ether, tetrahydrofuran and 1,4-dioxane, ketonic solvents such as acetone and methyl ethyl ketone, ester solvents such as methyl acetate and ethyl acetate, aprotic polar solvents such as dimethylformamide, dimethylsulfoxide and dimethylacetamide, acetonitrile, water, etc. Further, examples of the base include carbonate salts such as sodium hydroxide and potassium hydroxide, metal alcoholates such as sodium methylate and sodium ethylate, alkali metal hydrides such as sodium hydride and potassium hydride, and lithium amides such as lithium diethylamide, lithium diisopropylamide and lithium bis(trimethylsilyl)amide.
Further, examples of the alkylating agent include lower alkyl halides such as methyl iodide, methyl bromide, ethyl iodide and ethyl bromide, diazoalkanes such as diazomethane and diazoethane, sulfonic acid esters such as methyl trifluoromethanesulfonate, ethyl trifluoromethanesulfonate and methyl fluorosulfonate, and alkyloxonium salts such as trimethyloxonium tetrafluroborate and triethyloxonium tetrafluoroborate. ##STR42## (wherein R.sup.3, R.sup.5, R.sup.6, X, W, Z.sup.1, Z.sup.2, R.sup.1 and R.sup.2 are as defined hereinbefore, and E represents an organic amine in the form of a racemic compound or optically active compound).
In the above reaction formula of the Process A-6, a salt of the formula (I-j) can be prepared by reacting a compound of the formula (.+-.)-(I-a) with a suitable organic base E in the presence of a suitable solvent in the temperature range of room temperature to the boiling point of the solvent. This salt can be reconverted to (.+-.)-(I-a) by reaction with a suitable acid.
Further, an optically active salt (I-j) can be prepared by reacting a racemic compound represented by the above formula (.+-.)-(I-a) with a suitable optically active amine E in the presence of a suitable solvent in the temperature range of room temperature to the boiling point of the solvent to give a diasteromer mixture and recrystallizing this mixture in a suitable solvent in the temperature range of room temperature to the boiling point of the solvent, followed by purification. Further, (+)- or (-)- (I-a) can be prepared by decomposing this salt with a suitable acid in the presence of a suitable solvent in the temperature range of room temperature to the boiling point of the solvent.
When a solvent is used in this reaction, examples thereof include hydrocarbonic solvents such as benzene, toluene and xylene, halogenated hydrocarbonic solvents such as dichloromethane and chloroform, etherial solvents such as diethyl ether, diisopropyl ether, tetrahydrofuran and 1,4-dioxane, ketonic solvents such as acetone and methyl ethyl ketone, ester solvents such as methyl acetate and ethyl acetate, aprotic polar solvents such as dimethylformamide, dimethylsulfoxide and dimethylacetamide, alcoholic solvents such as methyl alcohol, ethyl alcohol, n-propyl alcohol, isopropyl alcohol and tert-butyl alcohol, acetonitrile, water, etc.
Further, examples of the amine include ammonia, alkylamines such as methylamine, ethylamine, 1-propylamine, isopropylamine, n-butylamine, sec-butylamine, iso-butylamine, tert-butylamine, n-hexylamine, n-octylamine, n-nonylamine and n-decylamine, and organic amines in (+) form or (-) form such as brucine, cinchonidine, dehydroabiethylamine, 1-phenylethylamine, morphine, deoxyephedrine, strychnine, quinine, amphetamine, threo-2-amino-1-paranitrophenyl-1,3-propanediol and 1-(1-naphthyl)ethylamine.
Further, examples of the acid include mineral acids such as hydrochloric acid, sulfuric acid and phosphoric acid. ##STR43## (wherein R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, X, W, Z.sup.1, Z.sup.2 are as defined hereinbefore).
In the above reaction formula of the Process A-7, a compound represented by the formula (I-i) can be prepared by reacting a compound of the formula (I-a) with a suitable sulfurizing agent without any solvents on in the presence of a suitable solvent in the temperature range of room temperature to the boiling point of the solvent for 1 to 24 hours.
When a solvent is used in this reaction, examples thereof include, for example, hydrocarbonic solvents such as benzene, toluene and xylene, organic bases such as pyridine and triethylamine, halogenated hydrocarbonic solvents such as dichloromethane and chloroform, etherial solvents such as diethyl ether, diisopropyl ether, tetrahydrofuran and 1,4-dioxane, acetonitrile, water, etc.
Further, examples of the sulfurizing agent include Lawesson's reagent, phosphorus pentasulfide, hydrogen sulfide, etc.
EXAMPLE 1
Preparation of 1-fluoro-2-hydroxy-1-cyclopentanecarboxylic acid methyl ester in cis form (compound number 2a)
First, methyl 1-fluoro-2-oxocyclopentanecarboxylate was prepared from methyl 2-oxocyclopentanecarboxylate referring to the process described in Tetrahedron Letters 27 (37), 4465-4468 (1986). Then, 2.3 g (0.032 mol) of trimethylamine-borane complex and 5.0 g (0.031 mol) of the methyl 1-fluoro-2-oxocyclopentanecarboxylate were added to 50 ml of dry diglyme, the resulting solution was cooled to 0.degree. C., and while it as stirred in the stream of nitrogen, 0.8 ml of boron trifluoride etherate was added dropwise. The resulting solution was stirred at room temperature for 1 hour and then poured into a saturated aqueous sodium bicarbonate solution, followed by extraction with ether. The ether layer was washed with water and dried over anhydrous magnesium sulfate, and the solvent was distilled away to obtain 4.5 g (yield: 89%) of the objective methyl 1-fluoro-2-hydroxycyclopentanecarboxylate in cis form (compound number 2a; the substance such that the substituent at the 2-position is supposed to take cis configuration when the methoxycarbonyl group at the 1-position is taken as a standard) which contains almost no the same in trans form.
.sup.1 H-NMR (.delta., CDCl.sub.3): 1.33-3.03 (6H,m), 3.82 (3H,S), 4.07-4.60 (1H,m) ppm
EXAMPLE 2
Preparation of 1-fluoro-2-hydroxy-1-cyclopentanecarboxylic acid methyl ester in trans form (compound number 2b)
3.1 ml (0.031 mol) of dimethylsulfide-borone complex was added to 50 ml of dry tetrahydrofuran at room temperature in the stream of nitrogen. The resulting solution was cooled to 0.degree. C. and 5.0 g (0.031 mol) of 1-fluoro-2-oxocyclopentanecarboxylic acid methyl ester synthesized according to the literature shown in Example 1 was added dropwise. The mixture was stirred at room temperature for 1 hour, the solvent was distilled away under reduced pressure, and the remaining liquid was poured into water, followed by extraction with ethyl acetate. The ethyl acetate layer was washed with water and dried over anhydrous magnesium sulfate, and the solvent was distilled away to obtain 3.7 g (yield: 73%) of a stereoisomer mixture comprising methyl 1-fluoro-2-oxocyclopentanecarboxylate in cis form (compound number 2a; the substance such that the substituent at the 2-position is supposed to take cis configuration when the methoxycarbonyl group at the 1-position is taken as a standard) and same in the trans form (compound 2b; the substance such that the substituent at the 2-position is supposed to take trans configuration when the methoxycarbonyl group at the 1-position is taken at a standard). As a result of analysis by gas chromatography, the formation ratio of cis/trans was 9/91. This mixture was further purified by silica gel column chromatography (developing solvent: hexane/ethyl acetate=10/1) to obtain 3.3 g (yield: 65%) of the objective methyl 1-fluoro-2-hycroxycyclopentanecarboxylate in trans form (compound number 2b).
.sup.1 H-NMR (.delta., CDCl.sub.3): 1.30-2.90 (6H,m), 3.80 (3H,S), 4.03-4.63 (1H,m) ppm
EXAMPLE 3
Preparation of 1-fluoro-2-hydroxy-1-cyclohexanecarboxylic acid ethyl ester cis form and trans form (compound numbers 73a and 73b)
3.1 ml (0.031 mol) of dimethyl sulfide-borone complex was added to 50 ml of dry tetrahydrofuran at room temperature in the stream of nitrogen. The resulting solution was cooled to 0.degree. C. and 5.8 g (0.031 mol) of 1-fluoro-2-oxocyclohexanecarboxylic acid ethyl ester synthesized according to the process of Example 1 was added dropwise. The mixture was stirred at room temperature for 1 hour, the solvent was distilled away under reduced pressure, the remaining liquid was poured into water, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with water and dried over anhydrous magnesium sulfate, and the solvent was distilled away to obtain 4.3 g (yield: 85%) of a stereoisomer mixture comprising 1-fluoro-2-hydroxycyclohexanecarboxylic acid ethyl ester in cis form (compound number 73a; the substance such that the substituent at the 2-position is supposed to take cis configuration when the ethoxycarbonyl group at the 1-position is taken as a standard) and the same in trans form (compound number 73b; the substance such that the substituent at the 2-position is supposed to take trans configuration when the ethoxycarbonyl group at the 1-position is taken as a standard). This mixutre was further purified by silica gel column chromatography (developing solvent: hexane/ethyl acetate=10:1) to obtain 1.6 g (yield: 27.2%) of the objective 1-fluoro-2-hydroxycyclohexanecarboxylic acid ethyl ester in cis form (compound number 73a) and 2.4 g (yield: 40.7%) of the same in trans form (compound number 73b).
EXAMPLE 4
Preparation of 1-fluoro-2-hydroxy-1-cycloheptanecarboxylic acid methyl ester in cis form and trans form (compound numbers 134a and 134b)
First, a raw material 1-fluoro-2-oxocycloheptanecarboxylic acid methyl ester was synthesized as follows referring to the process of the literature shown in Example 1. 0.88 g (22 mmol) of sodium hydride (60% suspension in mineral oil) was added to 45 ml of dry tetrahydrofuran, and while the mixture was stirred in the range of -5.degree. C. to 0.degree. C., 3.4 g (20 mmol) of 2-oxocycloheptanecarboxylic acid methyl ester was added dropwise. At the time when the generation of hydrogen gas ceased, 5.8 g (20 mmol) of N-fluoro-2,4,6-trimethylpyridinium triflate was added, the temperature of the mixture was allowed to get back to room temperature, and stirring was continued for further 2 hours. The tetrahydrofuran was distilled away, the contents were poured into a 1N diluted aqueous hydrochloric acid water, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was thoroughly washed with a diluted aqueous hydrochloric acid solution, and further successively washed with saturated saline, a saturated aqueous sodium bicarbonate solution and saturated saline. After drying with anhydrous magnesium sulfate, the solvent was distilled away to obtain 2.63 g (yield: 70%) of the raw material 1-fluoro-2-oxo-1-cycloheptanecarboxylic acid methyl ester.
25 ml of methanol was cooled to 5.degree. C. and 70 mg (1.8 mmol) of sodium hydroxide and 0.14 g (3.7 mmol) of sodium borohydride were added. To the resulting solution was added dropwise in the range of 5.degree. C. to 10.degree. C. 10 ml of a methanol solution of 2.5 g (13.3 mmol) of the 1-fluoro2-oxo-1-cycloheptanecarboxylic acid methyl ester. After stirring at room temperature for 2 hours, the contents were poured into saturated saline, followed by extraction with ethyl acetate. The extract was successively washed with diluted hydrochloric acid, saline, a saturated sodium bicarbonate solution and saline. The ethyl acetate layer was dried over anhydrous sodium sulfate and the solvent was distilled away to obtain 2.3 g of the crude product. The crude product was purified by silica gel column chromatography (developing solvent: hexane/isopropyl alcohol=99/1) to obtain 1.4 g (yield: 55.4%) of 1-fluoro-2-hydroxycycloheptanecarboxylic acid methyl ester in cis form (compound number 134a; the substance such that the substituent at the 2-position is supposed to take cis configuration when the methoxycarbonyl group at the 1-position is taken as a standard):
.sup.1 H-NMR (.delta., CDCl.sub.3): 0.98-2.62 (10H,m), 3.80 (3H,S), 3.88-4.35 (1H,m) ppm
and 0.6 g (yield: 23.7%) of the same in trans form (compound number 134b; the substance such that the substituent at the 2-position is supposed to take trans configuration when the methoxycarbonyl group at the 1-position is taken as a standard):
.sup.1 H-NMR (.delta., CDCl.sub.3): 1.18-2.75 (10H,m), 3.78 (3H,S), 3.90-4.40 (1H,m) ppm
EXAMPLE 5
Preparation of 1-fluoro-2-hydroxy-1-cyclooctanecarboxylic acid ethyl ester (compound number 153)
2-Oxo-1-cyclooctanecarboxylic acid ethyl ester was synthesized from cyclooctanone according to the process disclosed in Organic Synthesis, collective volume 5, page 198 (1973). The obtained compound was fluorinated and reduced in the same manner as in Example 4 to obtain a mixture of 1-fluoro-2 hydroxycyclooctanecarboxylic acid ethyl ester in cis form (the substance such that the substituent at the 2-position is supposed to take cis configuration when the methoxycarbonyl group at the 1-position is taken as a standard) and the same in trans form (the substance such that the substituent at the 2-position is supposed to take trans configuration when the methoxycarbonyl group at the 1-position is taken as a standard).
.sup.1 H-NMR (.delta., CDCl.sub.3): 1.35-2.87 (12H,m), 1.30 (3H,t,J=7.0Hz), 3.80-4.40 (1H,m), 4.25 (2H q,J=7.0Hz) ppm
EXAMPLE 6
Preparation of 2-acetoxy-1-fluoro-1-cyclopentanecarboxylic acid methyl ester in cis form (compound number 3a)
0.32 g (3 mmol) of acetic anhydride and a catalytic amount of concentrated sulfuric acid were added at room temperature to 0.5 g (3 mmol) of 1-fluoro-2-hydroxycyclopentanecarboxylic acid methyl ester in cis form (compound number 2a) synthesized in Example 1, and the mixture was stirred for 5 hours. The reaction solution was poured into ice water and extracted with ethyl acetate, and the extract was successively washed with saturated saline, a saturated aqueous sodium bicarbonate solution and saturated saline. The ethyl acetate layer was dried over anhydrous magnesium sulfate and the solvent was distilled away to obtain 0.45 g (yield: 72%) of the objective 2-acetoxy-1-fluoro-1-cyclopentanecarboxylic acid methyl ester in cis form (compound number 3a).
.sup.1 H-NMR (.delta., CDCl.sub.3): 1.50-2.93 (6H,m), 2.02 (3H,S), 3.77 (3H,s), 5.00-5.50 (1H,m) ppm
EXAMPLE 7
Preparation of 2-benzoyloxy-1-fluoro-1-cyclopentanecarboxylic acid methyl ester in cis form (compound number 4a)
.045 g (3 mmol) of benzoyl chloride was added under ice cooling to a mixture of 0.5 g (3 mmol) of the 1-fluoro-2-hydroxy-1-cyclopentanecarboxylic acid methyl ester in cis form (compound number 2a) synthesized in Example 1 and 2 ml of pyridine, the temperature of the mixture was brought back to room temperature, and the mixture was stirred for 5 hours. The reaction solution was poured into a diluted aqueous hydrochloric acid solution and extracted with ethyl acetate and the extract was successively washed with saturated saline, a saturated aqueous sodium bicarbonate solution and saturated saline. The ethyl acetate layer was dried over anhydrous magnesium sulfate and the solvent was distilled away to obtain 0.68 g (yield: 84%) of the objective 2-benzoyloxy-1-fluoro-cyclopentanecarboxylic acid methyl ester in cis form (compound number 4a).
.sup.1 H-NMR (.delta., CDCl.sub.3): 1.47-3.03 (6H,m), 3.73 (3H,S), 5.20-5.73 (1H,s), 7.20-8.22 (5H,m) ppm
EXAMPLE 8
Preparation of 1-fluoro-2-methanesulfonyloxy-1-cyclopentanecarboxylic acid methyl ester in cis form (compound number 5a)
0.36 g (3 mmol) of methanesulfonyl chloride was added under ice cooling to a mixture of 0.5 g (3 mmol) of 1-fluoro-2-hydroxy-1-cyclopentanecarboxylic acid methyl ester in cis form (compound number 2a) synthesized in Example 1 and 2 ml of pyridine, and the mixture was stirred at 0.degree. C. for 5 hours. The reaction solution was poured into a ice water and extracted with ether, and the ether layer was washed with cold water. The ether layer was dried over anhydrous magnesium sulfate and the solvent was distilled away to obtain 0.59 g (yield: 80%) of the desired 2-methanesulfonyloxy-1-fluoro-1-cyclopentanecarboxylic acid methyl ester in cis form (compound number 5a).
.sup.1 H-NMR (.delta., CDCl.sub.3): 1.52-2.63 (6H,m), 3.00 (3H,s), 3.81 (3H,s), 4.80-5.28 (1H,m) ppm
EXAMPLE 9
Preparation of 1-fluoro-2-paratoluenesulfonyloxy-1-cyclopentanecarboxylic acid methyl ester in cis form (compound number 6a)
0.56 g (3 mmol) of paratoluenesulfonyl chloride was added under ice cooling to a mixture of 0.5 g (3 mmol) of 1-fluoro-2-hydroxy-1-cyclopentanecarboxylic acid methyl ester in cis form (compound number 2a) synthesized in Example 1 and 2 ml of pyridine, the temperature of the resulting mixture was brought back to room temperature, and mixture was stirred for 5 hours. The reaction solution was poured into a ice water and extracted with ether, and the extract was washed with cold water. The ether layer was dried over anhydrous magnesium sulfate and the solvent was distilled away to obtain 0.77 g (yield: 79%) of the objective 2-paratoluenesulfonyloxy-1-fluoro-1-cyclopentanecarboxylic acid methyl ester in cis form (compound number 6a).
.sup.1 H-NMR (.delta., CDCl.sub.3): 1.37-2.37 (6H,m), 2.46 (3H,s), 3.70 (3H,s), 4.27-5.17 (1H,m), 7.00-8.20 (5H,m) ppm
EXAMPLE 10
Preparation of 1-fluoro-2-methoxy-1-cyclopentanecarboxylic acid methyl ester in trans form (compound number 13b)
0.12 g (3 mmol) of sodium hydride (60% suspension in mineral oil) was added to 5 ml of dry dimethylsulfoxide, and the mixture was cooled to 5.degree. C. To the resulting solution was added dropwise 5 ml of the dimethylsulfoxide solution of 0.5 g (3 mmol) of 1-fluoro-2-hydroxy-1-cyclopentanecarboxylic acid methyl ester in trans form (compound number 2b) synthesized in Example 2, then 0.47 g (3.3 mmol) of methyl iodide was added. The temperature of the mixture was brought back to room temperature, and the mixture was stirred for 2 hours. The reaction solution was poured into a diluted aqueous hydrochloric acid solution and extracted with ethyl acetate, and the extract was successively washed with saturated saline, a saturated aqueous sodium bicarbonate solution and saturated saline. The ethyl acetate layer was dried over anhydrous magnesium sulfate, and the solvent was distilled away to obtain 0.33 g (yield: 62%) of the objective 2-methoxy-1-fluoro-1-cyclopentanecarboxylic acid methyl ester in trans form (compound number 13b).
.sup.1 H-NMR (.delta., CDCl.sub.3): 1.42-2.68 (6H,m), 3.35 (3H,s), 3.80 (3H,s), 4.03-5.00 (1H,m) ppm
EXAMPLE 11
Preparation of 1-fluoro-2-methoxy-1-cyclopentanecarboxylic acid in trans form (compound number 12b)
0.35 g (2 mmol) of 1-fluoro-2-methoxy-1-cyclopentanecarboxylic acid methyl ester in trans form (compound number 13b) synthesized in Example 10 was dissolved in 5 ml of methanol, and 8 ml of a 5% aqueous potassium hydroxide solution was added, and mixture was stirred at room temperature for 2 hours. The reaction solution was poured into a diluted aqueous hydrochloric acid solution and extracted with ether, and ether layer was dried over anhydrous magnesium sulfate, and the solvent was distilled away to obtain 0.26 g (yield: 81%) of the objective 2-methoxy-1-fluoro-1-cyclopentanecarboxylic acid in trans form (compound number 12b).
.sup.1 H-NMR (.delta., CDCl ): 1.43-2.60 (6H,m), 3.43 (3H,s), 3.77-4.67 (1H,m), 8.47 (1H,s) ppm
EXAMPLE 12
Preparation of 1-fluoro-2-methoxy-1-cyclopentanecarboxylic acid tertiary butyl ester in cis form (compound number 20a)
The 1-fluoro-2-hydroxy 1-cyclopentanecarboxylic acid methyl ester in cis form (compound number 2a) synthesized in Example 1 was methylated in the same manner as in Example 10 and further hydrolyzed in the same manner as in Example 11 to obtain 1-fluoro-2-methoxy-1-cyclopentanecarboxylic acid in cis form (compound number 12a). 0.4 g (2.7 mmol) of this carboxylic acid, 0.20 g (2.7 mmol) of tertiary butyl alcohol, 0.56 g (3.7 mmol) of dicyclohexylcarbodiimide and 15 mg of 4,4-dimethylaminopyridine were mixed in 5 ml of ether and stirred at room temperature for 2 hours. The reaction solution was filtered, ether was added to the filtrate, and the mixture was successively washed with a diluted hydrochloric acid solution, saturated saline, a saturated aqueous sodium bicarbonate solution and saturated saline. The ether layer was dried over anhydrous magnesium sulfate, and the solvent was distilled away to obtain 0.31 g (yield: 56%) of the objective 2-methoxy-1-fluoro-1-cyclopentanecarboxylic acid tertiary butyl ester in cis form (compound number 20a).
.sup.1 H-NMR (.delta., CDCl.sub.3): 1.47-2.80 (6H,m), 1.53 (9H,s), 3.37 (3H,s), 3.57-4.37 (1H,m) ppm
EXAMPLE 13
Preparation of 1-fluoro-2-methoxy-1-cyclopentanecarboxylic acid tertiary butylamide in cis form (compound number 29a)
0.4 g (2.7 mmol) of 1-fluoro-2-methoxy-1-cyclopentanecarboxylic acid in cis form (compound number 12a) disclosed in Example 12 and 0.27 g (2.7 mmol) of triethylamine were dissolved in 10 ml of tetrahydrofuran, and the solution was cooled to 0.degree. C. 0.29 g (2.7 mmol) of ethyl chlorocarbonate was added dropwise, the mixture was stirred at 0.degree. C. for 1 hour, 0.24 g (3.2 mmol) of tertiary butylamine was add, and the mixture was further stirred at room temperature for 1 hour. The reaction mixture was poured into water and extracted with ether, and the extract was washed with saturated saline. The ether layer was dried over anhydrous magnesium sulfate, and the solvent was distilled away to obtain 0.3 g (yield: 55%) of the objective 1-fluoro-2-methoxy-1-cyclopentanecarboxylic acid tertiary butylamide in cis form (compound number 29a).
.sup.1 H-NMR (.delta., CDCl.sub.3): 1.43-2.57 (6H,m), 1.39 (9H,s), 3.37 (3H,s), 3.83-4.28 (1H,m) ppm
EXAMPLE 14
Preparation of 1-fluoro-2-methoxy-1-cyclopentanecarboxylic acid tertiary butyl thiol ester in trans form (compound number 38b)
0.4 g (2.7 mmol) of 1-fluoro-2-methoxy-1-cyclopentanecarboxylic acid in trans form (compound number 12b) synthesized in Example 11 and 0.24 g (2.7 mmol) of tertiary butyl thiol were dissolved in 5 ml of ether, 0.56 g (2.7 mmol) of dicyclohexylcarbodiimide and 15 mg of 4,4-dimethylaminopyridine were added, and the mixture was stirred at room temperature for 2 hours. The reaction solution was filtered, ether was added to the filtrate, and the mixture was successively washed with a diluted aqueous hydrochloric acid solution, saturated saline, a saturated aqueous sodium bicarbonate solution and saturated saline. The ether layer was dried over anhydrous magnesium sulfate, and the solvent was distilled away to obtain 0.48 g (yield: 83%) of the objective 2-methoxy-1-fluoro-1-cyclopentanecarboxylic acid tertiary butyl thiol ester in trans form (compound number 38b).
.sup.1 H-NMR (.delta., CDCl.sub.3): 1.30-2.60 (6H,m), 1.48 (9H,s), 3.33 (3H,s), 3.42-4.37 (1H,m) ppm
EXAMPLE 15
Preparation of 2-benzyloxy-1-fluoro-1-cyclohexanecarboxylic acid ethyl ester in trans form (compound number 107b)
0.5 g (3 mmol) of 1-fluoro-2-hydroxy-1-cyclohexanecarboxylic acid ethyl ester in trans form (compound number 73b) synthesized in Example 3 was dissolved in 5 ml of tetrahydrofuran, the mixture was cooled to 0.degree. C., and 0.12 g (3 mmol) of sodium hydride (60% suspension in mineral oil) was added. At the time when the generation of hydrogen gas ceased, 11 mg (3 mmol) of tetra-n-butylammonium iodide and 0.52 g (3 mmol) of benzyl bromide were successively added. After stirring at room temperature for 5 hours, the reaction solution was poured into a diluted aqueous hydrochloric acid solution and extracted with ethyl acetate. The ethyl acetate layer was successively washed with saturated saline, a saturated aqueous sodium bicarbonate solution and saline and dried over anhydrous magnesium sulfate, and the solvent was distilled away to obtain 0.3 g (yield: 36%) of the objective 2-benzyloxy-1-fluoro-1-cyclohexanecarboxylic acid ethyl ester in trans form (compound number 107b).
.sup.1 H-NMR (.delta., CDCl.sub.3): 1.25 (3H,t,J=7Hz), 1.23-2.30 (8H,m), 3.23-4.00 (1H,m), 4.18 (2H,q,J=7Hz), 4.43 (1H,d,J=12Hz), 4.60 (1H,d,J=12Hz), 7.23 (5H,s) ppm
EXAMPLE 16
Preparation of 2-benzyloxy-1-fluoro-1-cyclo hexanecarboxylic acid in cis form (compound number 105a)
The 1-fluoro-2-hydroxy-1-cyclohexanecarboxylic acid ethyl ester in cis form (compound number 73a) synthesized in Example 3 was benzylated in the same manner as in Example 15 to obtain 2-benzyloxy-1-fluoro1-cyclohexanecarboxylic acid ethyl ester in cis form (compound number 107a). The compound hydrolyzed in the same manner as in Example 11 to obtain the objective 2-benzyloxy-1-fluoro-1-cyclohexanecarboxylic acid in cis form (compound number 105a).
.sup.1 H-NMR (.delta., CDCl.sub.3): 0.80-2.85 (8H,m), 3.28-4.12 (1H,m), 4.60 (1H,s), 7.27 (5H,s) ppm
EXAMPLE 17
Preparation of ethyl 1-chloro-2-hydroxy-1-cyclohexanecarboxylate (compound number 168)
First, ethyl 1-chloro-2-oxocyclohexanecarboxylate was prepared from ethyl 2-oxocyclohexanecarboxylate referring to the process described in Organic Synthesis volume 4, page 162. 17 g (0.1 mol) of ethyl 2-oxocyclohexanecarboxylate was dissolved in 50 ml of carbon tetrachloride, and to the solution was added dropwise 14.8 g (0.11 mol) of sulfuryl chloride dissolved in 15 ml of carbon tetrachloride at 0.degree. C. After stirring at room temperature for 2 hours, the reaction solution was poured into 100 ml of ice water, the mixture was extracted three times with 50 ml each of carbon tetrachloride, and the extract was washed twice with 75 ml each of saturated aqueous sodium bicarbonate and once with 75 ml of saturated saline and dried over anhydrous magnesium sulfate. The solvent was distilled away to obtain 18 g (yield: 88%) of ethyl 1-chloro-2-oxocyclohexanecarboxylate. 1.22 ml (2 mmol) of dimethyl sulfide borane was dissolved in 40 ml of tetrahydrofuran, and 2.5 g (12 mmol) of ethyl 1-chloro-2-oxocyclohexanecarboxylate was added dropwise at -5.degree. C. to 0.degree. C. After stirring at 0.degree. C. for 1 hour, the solvent was distilled away under reduced pressure and the reaction solution was poured into 50 ml of ice water. The mixture was extracted three times with 50 ml each of ethyl acetate, and the resulting organic layer was washed once with 75 ml of saturated saline and dried over anhydrous magnesium sulfate. The solvent was distilled away to obtain 2.2 g of a stereoisomer mixture of ethyl 1-chloro-2-hydroxy-1-cyclohexanecarboxylate.
.sup.1 H-NMR: 0.84-3.02 (8H,m), 1.3 (3H,t,J=7Hz), 3.25-4.4.8 (1H,m), 4.25 (2H,q,J=7Hz) ppm
EXAMPLE 18
Preparation of methyl 1-fluoro-2-mercapto1-cyclohexanecarboxylate (compound number 164)
First, ethyl 1-fluoro-2-oxocyclohexanecarboxylate was synthesized according to the process described in Example 1. Then, referring to the process described in Comptes Rendus Hebdomadaire des Seances de l'Academie des Sciences Serie C No. 279, pages 529 to 531 (1974), 5.3 g (30 mmol) of this ester was dissolved in 50 ml of methanol was carried out at -78.degree. C. for 2 hours and at -10.degree. C. for 2 hours while hydrogen sulfide and hydrogen chloride were blown into the solution at the same time. The reaction solution was poured into ice water and extracted with ether. The ether layer was washed with saturated saline and the solvent was distilled away to obtain 4.0 g of the crude product of methyl 1-fluoro-2-mercapto-2-cyclohexenecarboxylate. This was dissolved in 30 ml of methanol, 200 mg (5 mmol) of sodium hydroxide was added, and the mixture was cooled to 0.degree. C. 740 mg (20 mmol) of sodium borohydride was added and reaction was carried out at 0.degree. C. for 2 hours. The reaction solution was poured into saturated saline and extracted with ether. The solvent was distilled away and the resulting product was purified by silica gel column chromatography (developing solvent: hexane/ethyl acetate =20/1) to obtain 580 mg (yield: 10 %) of the objective methyl 1-fluoro-2-mercapto-1-cyclohexanecarboxylate.
Mass / M/z=192 (M.sup.+)
EXAMPLE 19
Preparation of 3-ethoxycarbonyl-3-fluoro4-hydroxy-tetrahydro-4H-pyran (compound number 242)
First, 3-ethoxycarbonyl-tetrahydro-4H-pyran4-one was synthesized referring the process described in Japan Laid-Open Patent Publication No. 32080/90. Then this ester was fluorinated in the same manner as in Example 4 to prepare 3-ethoxycarbony-3-fluoro-tetrahydro-4H-pyran-4-one which was then reduced in the same manner as in the same example to prepare 3-ethoxycarbonyl-3-fluoro-4-hydroxytetrahydro-4H-pyran.
.sup.1 H-NMR: 1.3 (3H,t,J=7Hz), 1.5-2.17 (2H,m), 2.17-2.67 (1H,m), 3.22-4.53 (5H,m), 4.24 (2H,q,J=7Hz) ppm
EXAMPLE 20
Preparation of methyl 1-fluoro-2-(4,6-dimethoxypyrimidinyl-2-oxy)-1-cyclopentanecarboxylate in trans form (compound number 1003b)
1.55 g (9.6 mmol) of methyl 1-fluoro-2-hydroxycyclopentanecarboxylate in trans form prepared according to Example 1 was dissolved in 40 ml of dimethylformamide, to the solution were added 0.38 g (9.6 mmol) of sodium hydride (60% suspension in mineral oil) and 2.0 g (9.6 mmol) of 4,6-dimethoxy-2-methylsulfonylpyrimidine, and the mixture was stirred at room temperature for 5 hours. The reaction solution was poured in 150 ml of water and extracted three times with 50 ml each of ethyl acetate, and obtained organic layer was washed with water and dried over anhydrous magnesium sulfate. The solvent was distilled away to obtain 2.6 g of the crude product. This was purified by silica gel chromatography (developing solvent: hexane/ethyl acetate =10/1) to obtain 0.6 g (yield: 20.9%) of a substance supposed to be the desired methyl 1-fluoro-2-(4,6-dimethoxypyrimidinyl-2-oxy)-1-cyclopentanecarboxylate in trans form (compound number 1003b) (wherein the substituent at the 2 -position takes trans configuration when the methoxycarbonyl group at the 1-position is taken as a standard).
.sup.1 H-NMR (.delta., CDCl.sub.3): 1.53-2.77 (m,6H), 3.71 (s,3H), 3.87 (s,6H), 5.3-5.76 (m,1H), 5.63 (s,1H) ppm
EXAMPLE 21
Preparation of ethyl 3-(4,6-dimethoxy-2-fluoro-2-methylbutylate in erythro from and threo form (compound numbers 5158a and 5158b)
First, ethyl 2-fluoro-2-methylacetoacetate was prepared from ethyl 2-methylacetoacetate referring to the process described in Tetrahedron Letters 27 (No. 37), 4456-4468 (1986). This compound was reduced, referring to the process described in Journal of Organic Chemistry 27, 4141 (1962), to prepare a stereoisomer mixture of ethyl 2-fluoro-3-hydroxy-2-methylbutylate. 1.6 g (10 mmol) of this alcohol was dissolved in 40 ml of dimethylformamide, to the solution were added 0.4 g (10 mmol) of sodium hydride (60% suspension in mineral oil) and 2.2 g (10 mmol) of 4,6-dimethoxy-2-methylsulfonylpyrimidine, and the mixture was stirred at room temperature for 3 hours. The reaction solution was poured into 150 ml of water and extracted three times with 50 ml each of ethyl acetate, and the obtained organic layer was washed with water and dried over anhydrous magnesium sulfate. The solvent was distilled to obtain 1.9 g of the crude product. This was purified by silica gel chromatography (developing solvent: hexane/ethyl acetate=10/1) to obtain 0.9 g (yield: 30%) of a substance supposed to be the objective ethyl 3-(4,6-dimethoxypyrimidinyl-2-oxy)-2-fluoro-2-methylbutyrate in erythro form (compound number 5158a),
.sup.1 H-NMR (.delta., CDCl.sub.3): 1.40 (3H,t,J=7.0Hz), 1.38 (3H,d,J=6.0Hz), 1.63 (3H,d,J=20.2Hz), 3.92 (6H,s), 4.24 (2H,d,J=7.0Hz), 5.20-5.97 (1H,m), 5.68 (1H,s) ppm and 0.8 g (yield: 26%) of the same in threo form (compound number 5158b),
.sup.1 H-NMR (.delta., CDCl.sub.3): 1.22 (3H,t,J=7.0Hz), 1.45 (3H,d,J=6.0Hz), 1.61 (3H,d,J=21.6Hz), 3.93 (6H,s), 4.22 (2H,d,J=7.0Hz), 5.03-5.88 (1H,m), 5.67 (1H,s) ppm.
EXAMPLE 22
Preparation of 4-(4,6-dimethoxypyrimidinyl-2-oxy)-3-ethoxycarbonyl-3-fluorotetrahydro-4H-pyran in cis form (compound number 6084a) and in trans form (compound number 6084b)
1.9 g (10 mmol) of a stereoisomer mixture of 3-ethoxycarbonyl-3-fluorotetrahydro-4H-4-hydroxy-pyran prepared in Example 19 was dissolved in 40 ml of dimethylformamide, to the solution were added 0.4 g (10 mmol) of sodium hydride (60% suspension in mineral oil) and 2.2 g (10 mmol) of 4,6-dimethoxy-2-methylsulfonylpyrimidine, and the mixture was stirred at 0.degree. C. for 1 hour and at room temperature for 3 hours. The reaction solution was poured into 150 ml of water and extracted three times with 50 ml each of ethyl acetate, and the resulting organic layer was washed with water and dried over anhydrous magnesium sulfate. The solvent was distilled away to obtain 2.3 g of the crude product. This crude product was purified by silica gel chromatography (developing solvent: hexane/ethyl acetate=10/1) to obtain 1.1 g (yield: 34%) of the objective 4-(4,6-dimethoxypyrimidinyl-2-oxy)-3-ethoxycarbonyl-3-fluorotetrahydro-4H-pyran in cis form (compound number 6084a, the substance such that the substituent at the 2-position is supposed to take trans configuration when the ethoxycarbonyl group at the 1-position is taken as a standard),
.sup.1 H-NMR (.delta., CDCl.sub.3): 1.14 (3H,t,J=7.2Hz), 2.01-2.33 (2H,m), 3.79-4.32 (4H,m), 3.91 (6H,s), 4.07 (2H,q,J=7.2Hz), 5.61-5.63 (1H,m), 5.72 (1H,s) ppm
and 0.78 g (yield: 24%) of the same in trans form (compound number 6084b, the substance such the substituent at the 2-position is supposed to take trans configuration when the ethoxycarbonyl group at the 1-position is taken as a standard),
.sup.1 H-NMR (.delta., CDCl.sub.3): 1.19 (3H,t,J=7.2Hz), 2.21-2.28 (2H,m), 3.6-4.21 (4H,m), 3.91 (6H,s), 4.05 (2H,q,J=7.2Hz), 5.6-5.72 (1H,m), 5.71 (1H,s) ppm.
EXAMPLE 23
Preparation of ethyl 1-chloro-2-(4,6-dimethoxypyrimidinyl-2-oxy)-1-cyclohexanecarbonylate in trans form (compound number 1455b)
2.1 g (10 mmol) of ethyl 1-chloro-2-hydroxy1-cyclohexanecarboxylate synthesized according to Example 17 was dissolved in 30 ml of dimethylformamide, to the solution were added 0.4 g (10 mmol) of sodium hydride (60% suspension in mineral oil) and 2.2 g (10 mmol) of 4,6-dimethoxy-2-methylsulfonylpyrimidine, and the mixture was stirred at room temperature for 2 hours. The reaction solution was poured into 150 ml of water and extracted three times with 50 ml each of ethyl acetate, the obtained organic layer was washed with water and dried over anhydrous magnesium sulfate, and the solvent was distilled away to obtain 2.9 g of the crude product. The crude product was purified by silica gel chromatography (developing solvent: hexane/ethyl acetate=12/1) to obtain 0.33 g (yield: 10%) of a substance (compound number 1455b) supposed to be the objective ethyl 1-chloro-2-(4,6-dimethoxypyrimidinyl-2-oxy)-1-cyclohexanecarbonylate in trans form (wherein the substituent at the 2-position takes trans configuration when the ethoxycarbonyl group at the 1-position is taken as a standard).
EXAMPLE 24
Preparation of methyl 1-fluoro-2-(4,6-dimethoxypyrimidinyl-2-thio)-1-cyclohexanecarboxylate (compound number 1496)
In 10 ml of dimethylformamide were dissolved 192 mg (1 mmol) of methyl 1-fluoro-2-mercaptocyclohexanecarboxylate synthesized according to Example 18 and 218 mg (1 mmol) of 4,6-diethoxy-2-methylsulfonylpyrimidine, to the solution was added 166 mg (1.2 mmol) of potassium carbonate, and the mixture was stirred at room temperature for 5 hours. The reaction solution was poured into water and extracted three times with 30 ml of ethyl acetate, and the obtained organic layer was washed with water and dried over anhydrous magnesium sulfate. The solvent was distilled away to obtain 350 mg of the crude product. This was purified by silica gel chromtography (developing solvent: hexane/ethyl acetate=10/1) to obtain 257 mg (yield: 78%) the objective methyl 1-fluoro-2-(4,6-dimethoxypyrmidinyl-2-thio)-1-cyclohexanecarboxylate (compound number 1496),
.sup.1 H-NMR (.delta., CDCl.sub.3): 5.78 (s,1H), 3.90 (s,6H), 3.75 (s,3H), 1.1-3.3 (m,9H) ppm.
EXAMPLE 25
Preparation of 1-fluoro-2-(4,6-dimethoxypyrimidinyl-2-oxy)-1-cyclopentanecarboxylic acid in trans form (compound number 1002b)
0.6 g (2 mmol) of methyl 1-fluoro-2-(4,6-dimethoxypyrimidinyl-2-oxy)-1-cyclopentanecarboxylate in trans form (compound number 1003b) synthesized according to Example 20 was dissolved in a mixed solution of 5 ml of methanol and 10 ml of water, 0.34 g of potassium hydroxide was added, and the mixture was stirred at 40.degree. C. for 1 hour. The methanol was distilled away, 30 ml of water was added to the reaction solution, and the mixture was acidified with diluted hydrochloric acid and extracted three times with 30 ml each of ethyl acetate. The ethyl acetate layer was dried over anhydrous magnesium sulfate and the solvent was distilled away to obtain 0.27 g (yield: 47.2%) of the desired 1-fluoro2-(4,6-dimethoxypyrimidinyl-2-oxy)-1-cyclopentanecarboxylic acid in trans form (compound number 1002b). Melting point 122.degree.-124.degree. C.
EXAMPLE 26
Preparation of 1-fluoro-2-(4,6-dimethoxypyrimidinyl-2-oxy)-1-cyclohexanecarboxylic acid isopropylamine salt in trans form (compound number 1218b)
Ethyl 1-fluoro-2-hydroxy-cyclohexanecarboxylate synthesized according to Example 3 was converted successively according to the process of Examples 20 and 21 to obtain 1-fluoro-2-(4,6-dimethoxypyrimidinyl-2-oxy)-1-cyclohexanecarboxylic acid in trans form (compound number 1180b). To 5 ml of the ethanol solution of 0.4 g (1.34 mmol) of this compound was added at room temperature 0.88 g (1.5 mmol) of isopropylamine, and the mixture was stirred for 30 minutes and concentrated under reduced pressure to obtain 0.48 g (yield: 99%) of the objective 1-fluoro-2-(4,6-dimethoxypyrimidinyl-2-oxy)1-cyclohexanecarboxylic acid isopropylamine salt in trans form (compound number 1218b).
EXAMPLE 27
Preparation of 1-fluoro-2-(4,6-dimethoxypyrimidinyl-2-oxy) -1-cyclopentanecarboxylic acid isopropyl ester in trans form (compound number 1006b)
0.12 g (1.74 mmol) of isopropyl alcohol was added to 10 ml of an ether solution of 0.5 g (1.74 mmol) of 1-fluoro-2-(4,6-dimethoxypyrimidinyl-2-oxy)-1-cyclopentanecarboxylic acid (compound number 1002b) synthesized according to Example 25, and then 0.4 g (1.93 mmol) of dicyclohexylcarbodiimide and 20 mg of 4,4-dimethylaminopyridine were added at room temperature. After stirring for 2 hours, the reaction solution was filtered and the filtrate was concentrated to obtain the crude product. The crude product was purified by silica gel column chromatography (developing solvent: hexane/ethyl acetate=4/1) to obtain 0.4 g (yield: 70%) of the objective 1-fluoro-2-(4,6-dimethoxypyrimidinyl2-oxy)-1-cyclopentanecarboxylic acid isopropyl ester in trans form (compound number 1006b).
.sup.1 H-NMR (.delta., CDCl.sub.3): 1.16 (3H,d,J=6.2Hz), 1.26 (3H,d,J=6.2Hz), 1.51-2.68 (6H,m), 3.89 (6H,s), 5.03 (1H,sep), 5.66 (1H,s), 5.31-5.95 (1H,m) ppm
EXAMPLE 28
Preparation of 1-fluoro-2-(4,6-dimethoxypyrimidinyl-2-oxy)-1-cyclopentanecarboxylic acid ethanethiol ester in trans form (compound number 4228b)
0.14 ml (1.74 mmol) of ethanethiol was added to 10 ml of an ether solution of 0.5 g (1.74 mmol) of 1-fluoro-2-(4,6-dimethoxypyrimidinyl-2-oxy)-1-cyclopentanecarboxylic acid (compound number 1002b) synthesized according to Example 25, and then 0.4 g (1.93 mmol) of dicyclohexylcarbodiimide and 20 mg of 4,4-dimethylaminopyridine were added at room temperature. After stirring for 2 hours, the reaction solution was filtered and the filtrate was concentrated to obtain the crude product. This was purified by silica gel column chromatography (developing solvent: hexane/ethyl acetate =9/1) to obtain 0.3 g (yield: 52%) of the objective 1-fluoro-2-(4,6-dimethoxypyrimidinyl-2-oxy)-1-cyclopentanecarboxylic acid ethanethiol ester in trans form (compound number 4228b).
EXAMPLE 29
Preparation of N,N-dimethyl, 1-fluoro-2-(4,6-dimethoxypyrimidinyl-2-oxy)-1-cyclopentanecarboxylic amide in trans form (compound number 4010b)
6 ml of an tetrahydrofuran solution of 0.4 g (1.4 mmol) of 1-fluoro-2-(4,6-dimethoxypyrimidinyl-2-oxy)-1-cyclopentanecarboxylic acid (compound number 1002b) was cooled to 0.degree. C., and 0.19 ml (1.4 mmol) of triethylamine and 0.13 ml (1.4 mmol) of ethyl chlorocarbonate were added. After stirring at 0.degree. C. for 1 hour, 0.15 g of a 50% aqueous dimethylamine solution was added and the mixture was further stirred for 2 hours. Water was added to the reaction solution, the mixture was extracted with ether and the ether layer was successively washed with diluted hydrochloric acid and saturated saline. The ether layer was dried over anhydrous sodium sulfate, the solvent was distilled away and the crude product was purified by silica gel column chromatography (developing solvent: hexane/ethyl acetate=1/9) to obtain 0.29 g (yield: 68%) of the objective N,N-dimethyl, 1-fluoro-2-(4,6-dimethoxypyrimidinyl-2-oxy)1-cyclopentanecarboxamide in trans form (compound number 4010b).
.sup.1 H-NMR (.delta., CDCl.sub.3): 1.67-2.67 (6H,m), 2.73-3.20 (6H,m), 3.87 (6H,s), 5.62 (1H,s), 5.47-6.05 (1H,m) ppm
EXAMPLE 30
Preparation of methyl O-methoxycarbonylmethyl-1-fluoro-2-(4,6-dimethoxypyrimidinyl-2-oxy)-1-cyclopentanehydroxymate (compound number 4096b)
0.8 ml of triethylamine was added to 10 ml of a tetrahydrofuran solution of 0.8 g (2.8 mmol) of 1-fluoro-2-(4,6-dimethoxypyrimidinyl-2-oxy)-1-cyclopentanecarboxylic acid (compound number 1002b) synthesized according to Example 25, the mixture was cooled to 0.degree. C., and 0.26 ml (2.8 mmol) of ethyl chloroformate was added dropwise. After stirring for 1 hour, 0.36 g (3.4 mmol) of methyl aminooxyacetate was added and the mixture was further stirred for 2 hours. The reaction solution was poured into saturated saline and extracted with ether, the ether layer was successively washed with a diluted aqueous hydrochloric acid solution and saturated saline and dried over anhydrous sodium sulfate, and the solvent was distilled away to obtain the crude product. This was purified by silica gel column chromatography (developing solvent: hexane/ethyl acetate=4/1) to obtain 0.66 g (yield: 63%) of the objective N-methoxycarbonylmethoxy, 1-fluoro-2-(4,6-dimethoxypyrimidinyl-2-oxy)-1-cyclopentanecarboxamide (compound number 4048b).
.sup.1 H-NMR (.delta., CDCl.sub.3): 1.70-2.77 (6H,m), 3.36 (3H,s), 3.94 (6H,s), 4.41 (2H,s), 5.70 (1H,s), 5.33-6.00 (1H,m), 9.43-9.73 (1H,bs) ppm
Melting point: 68.degree.-70.2.degree. C.
Then, to 10 ml of an ether solution of 0.66 g (1.7 mmol) of this amide (compound number 4048b) was added under ice cooling an ether solution containing 1.5 equivalent amount of diazomethane, and the mixture was stirred for 1 hour. The excessive diazomethane was decomposed by the addition of acetic acid to the reaction solution, the solvent was distilled away, and the resulting crude product was purified by silica gel column chromatography (developing solvent: hexane/ethyl acetate =9/1) to obtain 0.67 g (yield: 97%) of the objective methyl O-methoxycarbonylmethyl-1-fluoro-2-(4,6-dimethoxypyrimidinyl-2-oxy)-1-cyclopentanehydroxymate (compound number 4096b).
.sup.1 H-NMR (.delta., CDCl.sub.3): 1.56-2.59 (6H,m), 3.69 (3H,s), 3.92 (6H,s), 4.10 (3H,s), 4.44 (2H,s), 5.66 (1H,s), 5.39-5.92 (1H,m) ppm
Melting point: 72.degree.-74.0.degree. C.
EXAMPLE 31
Preparation of 1-fluoro-2-(4,6-dimethoxypyrimidinyl-2-oxy)-1-cyclohexanethiocarboxamide in trans form (compound number 4379b)
Ethyl 1-fluoro-2-hydroxy-cyclohexanecarboxylate synthesized in Example 3 was successively converted according to the processes of Examples 20, 21 and 29 to obtain 1-fluoro-2-(4,6-dimethoxypyrimidinyl-2-oxy)-1-cyclohexanecarboxamide acid in trans form (compound number 4275b). To 5 ml of an ethylene glycol dimethyl ether solution of 0.32 g (1.07 mmol) of this compound was added 0.24 g (0.59 mmol) of Lawesson's reagent, and the mixture was refluxed with heating for 2 hours. The reaction solution was cooled to room temperature, poured into water and extracted with chloroform, the chloroform layer was dried over anhydrous sodium sulfate, the solvent was distilled away, and the crude product was purified by silica gel column chromatography (developing solvent: hexane/ethyl acetate=4/1) to obtain 0.05 g (yield: 15%) of the objective 1-fluoro-2-(4,6-dimethoxypyrimidinyl-2-oxy)-1-cyclohexanethiocarboxamide in trans form (compound number 4379b).
.sup.1 H-NMR (.delta., CDCl.sub.3): 1.00-2.83 (8H,m), 3.90 (6H,s), 4.93-5.83 (1H,m), 5,63 (1H,s), 6.00 (1H,bs), 6.53 (1H,bs) ppm
EXAMPLE 32
Preparation of ethyl 2-(4,6-dimethoxypyrimidin-2-yl)-thio-1-fluoro-2-cyclohexenecarboxylate (compound number 7004)
Referring to the process described in Bulletin des Societe Chimiques Belges volume 87, page 223 (1978), 5.4 g (30 mmol) of ethyl 1-fluoro-2-oxocyclohexanecarboxylate was dissolved in 50 ml of toluene, to this was added 6.0 g (15 mmol) of Lawesson's reagent, and reaction was carried out at 100.degree. C. for 5 hours. 100 ml of hexane was added, the precipitate was filtered out and the solvent was distilled away. The filtrate was purified by silica gel column chromatography (developing solvent: hexane / ethyl acetate=15/1) to obtain 1.1 g (yield: 18 % of ethyl 1-fluoro-2-mercapto-2-cyclohexenecarboxylate.
204 mg (1 mmol) of this ethyl 1-fluoro-2-mercaptocyclohexenecarboxylate and 218 mg (1 mmol) of 4,6-dimethoxy-2-methylsulfonylpyrimidine were dissolved in 10 ml of dimethylformamide, 166 mg (1.2 mmol) of potassium carbonate was added to the solution and the mixture was stirred at room temperature for 5 hours. The reaction solution was poured into 50 ml of water and extracted three times with 30 ml each of ethyl acetate, and the obtained organic layer was washed with water and dried over anhydrous magnesium sulfate. The solvent was distilled away to obtain 350 mg of the crude product. The crude product was purified by silica gel column chromatography (hexane: ethyl acetate=9:1) to obtain 240 mg (yield: 70%) of the objective ethyl 2-(4,6-dimethoxypyrimidine-2-yl)-thio-1-fluoro-2-cyclohexcarboxylate (compound number 7004).
EXAMPLE 33
Preparation of (+) and (-)-1-fluoro-2-(4,6-dimethoxypyrimidinyl-2-oxy)-1-cyclopentanecarboxylic acid in trans form (compound numbers 1002 b1 and 1002b2) and their methyl esters (compound numbers 1003bl and 1003b2)
In 40 ml of isopropyl alcohol was dissolved 6.15 g (21.5 mmol) of 1-fluoro-2-(4,6-dimethoxypyrimidinyl-2-oxy)-1-cyclopentanecarboxylic acid (compound number 1002b) synthesized according to Example 25, 7 g (21.5 mmol) of quinine was added, and the formed salt was dissolved under reflux with heating. After being left at room temperature overnight, the reaction solution was filtered to obtain 10.65 g of a salt (named the first crystals). This salt was then twice recrystallized from isopropyl alcohol to obtain 4.4 g of pure quinine salt of (+)-1-fluoro 2-(4,6-dimethoxypyrimidinyl-2-oxy)-1-cyclopentenecarboxylic acid in trans form. 3.54 g of this salt wad dissolved in 40 ml of 1N hydrochloric acid, 50 ml of ether was added and the mixture was stirred for 1 hours. The ether layer was separated and dried over anhydrous magnesium sulfate and the solvent was distilled away to prepare 1.49 g (24.2%) of the objective (+)-1-fluoro-2-(4,6-dimethoxypyrimidinyl-2-oxy)-1-cyclopentanecarboxylic acid in trans form (compound number 1002 bl). [
.alpha.].sub.D =+36.62.degree.
(c=0.071, i-Pr-OH)
The mother liquor after the recrystallization of the first crystalls was then concentrated, and 3.53 g of the deposited the quinine salt of (-)-1-fluoro-2-(4,6-dimethoxypyrimidinyl-2-oxy)-1-cyclopentanecarboxylic acid in trans form (compound number 1002b2) was decomposed in the same manner as above to prepare 1.09 g (17.7%) of the objective (-)-1-fluoro-2-(4,6-dimethoxypyrimidinyl-2-oxy)-1-cyclopentanecarboxylic acid in trans form (compound number 1002b2).
[.alpha.].sub.D.sup.30 =-38.55.degree.
(c=0.083, i-Pr-OH)
1.49 g of the thus obtained optically active carboxylic acid in (+) from (compound number 1002bl) was dissolved in 20 ml of ether, and a necessary amount of an ether solution of diazomethane was added under ice cooling to methylate the carboxylic acid. The excessive diazomethane was decomposed with acetic acid and the solvent was distilled away to obtain 1.5 g (95.6%) of the object (+)-1-fluoro-2-(4,6-dimethoxypyrimidinyl-2-oxy)-1-cyclopentanecarboxylic acid methyl ester in trans form (compound number 1003bl).
Analysis with an optical isomer-separating column (CHIRALCEL OD; manufactured by Daisel Co.) (solvent system: hexane/isopropyl alcohol=9/1, flow rate: 2 ml/min, detection wavelength: 254 nm) revealed that the ester was excessive in antipode by 99%.
Further 1.09 g of (-)-1-fluoro-2-(4,6-dimethoxypyrimidinyl-2-oxy)-1-cyclopentanecarboxylic acid in trans form (compound number 1002b2) was methylated in the same manner as in the (+) form compound to obtain 1.11 g (yield: 96.4%) of (-)-1-fluoro-2-(4,6-dimethoxypyrimidinyl-2-oxy)-1-cyclopentanecarboxylic acid methyl ester in trans form (compound number 1003b2). The analysis of this ester under the same conditions as in the (+) form compound revealed that the ester was excessive in antitope by 86.8%.
The halogen-containing compounds represented by the formula (I) of this invention have an excellent activity as a hebicide. When used as herbicides, the compounds represented by the formula (I) are mixed with agriculturally and forticulturally acceptable carrier(s) or diluent(s), additive(s) and auxiliary(ies) and the like by a method known per se and formulated into preparation forms usually used for pesticides, such as, for example, dusts, granules, wettable powders, emulsifiable concentrate liquids and flowables. Further, other pesticides such as, for example, fungicides, insecticides, acaricides, other herbicides, plant growth regulators, fertilizers or soil-improving agents can be mixed therewith or used together. Particularly by using the compounds represented by the formula (I) in a state such that they are mixed with other herbicides, the amounts of the chemicals to be used can be reduced and labors can be reduced, and further, the enlargement of weeding spectrum due to the synergism of both chemicals and a still higher effect due to potentiation can also be expected.
The following can, for example, be mentioned as specific examples of other herbicides usable in a state such that they are mixed with the compounds of the invention represented by the formula (I) (the words in the parentheses denote common names unless otherwise defined).
Carbamate herbicides
Methyl 3,4-dichlorophenylcarbamate (Swep), isopropyl 3-chlorophenylcarbamate (Chloroproham), S-(p-chlorobenzyl)-N,N-diethylthiocarbamate (Benthiocarb), S-ethyl N,N-hexamethylenethiocarbamate (Molinate), S-(1-methyl-1-phenylethyl) piperidine-1-carbothioate (Dimepiperate), S-benzyl N-ethyl-N-(1,2-dimethylpropyl) thiolcarbamate (Esprocarb), 3-(methoxycarbonylaminophenyl N-(3-methylphenyl) carbamate (Phenmedipham), ethyl 3-phenylcarbamoyloxyphenylcarbamate (Desmedipham), etc.
Urea herbicides
1-(.alpha., .alpha.-Dimethylbenzyl-3-(4-methylphenyl)urea Dymron), 3-(3,4-dichlorophenyl)-1,1-dimethylurea (Diuron), 1,1-dimethyl-3-(.alpha.,.alpha.,.alpha.-trifluoro-m-tolyl)urea (Fluometuron), 3-[4-(4-chlorophenoxy)phenyl)-1,1-dimethylurea (Chloroxuron), 3-(3,4-dichlorophenyl)-1-methoxy-1-methylurea (Linuron), 3-(4-chlorophenyl)-1-methoxy-1-methylurea (Monolinuron), 3-(4-bromo-3-chlorophenyl)-1-methoxy-1-methylurea (Chlorbromron), 1-(,-dimethylbenzyl)-3-(2-chlorobenzyl)urea (Code number JC-940), etc.
Haloaceta amide herbicides
2-Chloro-2',6'-dimethyl-N-methoxymethyla cetanilide (Alachlor), N-butoxymethyl-2-chloro-2',6'-diethlacetanilide (Butachlor), 2-chloro-2',6'-diethyl-N-(2-propoxyethyl) acetanilide (Pretilachlor), 2-chloro-N-isopropylacetanilide (Propachlor), etc.
Amide herbicides
3',4'-Dichloropropionanilide (Propanil), 2-bromo-N-(1,1-dimethylbenzyl)-3,3-dimethylbutanamide (Bromobutide), 2-benzothiazol-2-yloxy-N-methylacetanilide (Mefenacet), N,N-dimethyldiphenylacetamide (Diphenamide), etc.
Dinitrophenyl herbicides
4,6-dinitro-o-cresol (DNOC), 2-tert-butyl-4,6-dinitrophenol (Dinoterb), 2-sec-butyl-4,6-dinitrophenol (Dinoseb), N,N-diethyl-2,6-dinitro-4-trifluoromethyl-m-phenylenediamine (Dinitramine), .alpha.,.alpha.,.alpha.-trifluoro-2,6-dinitro-N,N-dipropyl-p-toluidine (Trifluralin), 4-methyl-sulfonyl-2,6-dinitro-N,N-dipropylaniline (Nitralin), N-(1-ethylpropyl)-2,6-dinitro-3,4-xylidine (Pendi-methalin), etc.
Phenoxy herbicides
2,4-Dichlorophenoxyacetic acid (2,4-D), 2,4,5-trichlorophenoxyacetic acid (2,4,5-T), 4-chloro-o-tolyloxacetic acid (MCPA), 4-(4-chloro-o-tolyloxy) butyric acid (MCPB), 2,4-dichlorophenoxy butyric acid (2,4-DB), 2,(4-chloro-o-tolyloxy) propionic acid (Mecoprop), 2-(2,4-dichlorophenoxy) propionic acid (Dichlorprop), (RS)-2-[4-(2,4-dichlorophenoxy)phenoxy propionic acid (Diclofop) and its esters, (RS)-2-[4-(5-trifluoromethyl-2-pyridyloxy)phenoxy] acid (Fluazifop) and its esters, 2-(2,4-dichloro-3-methylphenoxy) propionanilide (Cromeprop), S-ethyl 4-chloro-2-methylphenoxy-thioacetate (Phenothiol), 2-(2-naphthoxy) propionanilide (Naproanilide), etc.
Carboxylic acid herbicides
2,2-Dichporopropionic acid (Dalapone), trichloroacetic acid (TCA), 2,3,6-trichlorobenzoic acid (2,3,6-TBA), 3,6-dichloro-o-anisic acid (Dicamba), 3-amino-2,5-dichlorobenzoic acid (Chloromben), etc.
Organic phosphorus herbicides
O-Ethyl O-(2-nitro-5-methylphenyl)-N-sec-butyl-phosphoroamidethioate (Butamifos), O,O-diisopropyl S-(2-benzenesulfonylaminoethyl)phosphorodithioeate (SAP), S-(2-methylpiperidin-1-yl)carbonylmethyl O,O-dipropylphosphorodithioate (Piperophos), etc.
Benzonitrile herbicides
2,6-Dichlorobenzonitrile (Dichlobenil), 3,5-dibromo-4-hydroxybenzonitrile (Bromoxynil), 4-hydroxy-3,5-diiodobenzonitrile (Ioxynil), etc.
Diphenyl ether herbicides
2,4-Dichlorophenyl 4-nitrophenyl ether (Nitrofen), 2,4,6-trichlorophenyl 4'-nitrophenyl ether (Chlornitrofen), 2,4-dichlorophenyl 3-methoxy-4-nitrophenyl ether (Chlomethoxynil), methyl 5-(2,4-dichlorophenoxy)-2-nitrobenzoate (Bifenox), 4-nitrophenyl .alpha.,.alpha., -trifluoro-2-nitro-p-tolyl ether (Fluorodifen), 2-chloro-4-trifluoromethylphenyl 3-ethoxy-4-nitrophenyl ether (Oxygluorfen), 5-(2-chloro-.alpha.,.alpha.,.alpha.-trifluoro-p-tolyloxy)-2-nitrobenzoic acid (Acifluorfen), etc.
Triazine herbicides
4-Amino-3-methyl-6-phenyl-1-1,2,4-triazin-5-(4H)-one (Metribuzin), 2-chloro-4,6-bis-(ethylamino)1,3,5-triazine (Simazine), 2-chloro-4-ethylamino-6-isopropylamino-1,3,5-triazine (Atrazine), 2,4-bis(ethylamino)-6-methylthio-1,3,5-triazine (Simetryne), 2,4-bis(isopropylamino)-6-methylthio-1,3,5-ethylamino-6-methylthio-1,3,5-triazone (Dimethametryne), etc.
Sulfonylurea herbicides
2-Chloro-N-4-methoxy-6-methyl-1,3,5-triazin-yl) aminocarbonyl] benzenesulfonamide (Chlorsulfuron), methyl 2-{((4,6-dimethoxypyrimidin-2-yl) aminocabonyl) aminosulfonyl] methyl)benzoate (Bensulfuron methyl), Ethyl 2-[((4-chloro-6-methoxypyrimidin-2-yl) aminocarbonyl)aminosulfonyl)benzoate (Chlorimuron ethyl), etc.
Diazine herbicides
4-(2,4-Dichlorobenzoyl)-1,3-dimethylpyrazol-5-yl-p-toluenesulfonate (Pyrazolate), 1,3-dimethyl-4-(2,4-dichlorobenzoyl)-5-phenacyloxypyrazole (Pyrazoxyfen), 1,3-dimethyl-4-(2,4-dichloro-3-methyl-benzoyl)- 5-(4-methylphenacyloxy) pyrazole (Benzofenap), etc.
Other herbicides
3,6-Dichloropyridine-2-carboxylic acid (Clopyralid), 4-amino-3,5,6-trichloropyridine-2-carboxylic acid (Picloram), 5-amino-4-chloro-2-phenylpyridazin-3(2H)-one (Chloridazon),3-cyclohexyl-1,5,6,7-tetrahydrocyclo pentenopyrimidine-2,4(3H)-dione (Lenacil), 5-bromo-3-sec-butyl-6-methyluracil (Bromacil), 3-tert-butyl-5-chloro-6-methyluracil (Terbacil), 3-isopropyl-(1H)-2,1,3 benzothiadiazin-4(3H)-one 2,2-dioxide (Bentazone), N-1-naphthylphthalamic acid (Naptalam), etc.
As the agriculturally and horticulturally acceptable carrier(s) or dilutent(s) used in the formulation of the compund(s) of this invention alone or in mixing with other herbicide(s) solid or liquid carrier(s) usually used in agriculture is (are) used. Examples of the solid carriers include inorganic matters such as clays represented by the Kaolinite group, montmorillonite group, illite group and attapulgite group, talc, diatom earth, magnesium lime, apatite, zeolite, silicic anhydride and synthesized calcium silicate; vegetable organic matters such as soybean meal, tobacco meal, walnut meal, wheat flour, wood meal, starch and crystalline cellulose; synthetic and natural high molecular compounds such as coumarone resins, petroleum resins, alkyd resins, polyvinyl chloride, polyalkylene glycol, ketone resins, ester gum, copal gum and dammar gun; and further waxes such as carnauba wax and beeswax and urea, etc.
Examples of suitable liquid carriers include paraffin and naphthene hydrocarbons such as kerosene, mineral oil, spindle oil and white oil; aromatic hydrocarbons such as toluene, xylene, ethylbenzene, cumene and methyl naphthalene; ethers such as dioxane and tetrahydrofuran; ketones such as methyl ethyl ketone, diisobutyl ketone, cyclohexanone, acetophenone and isophorone; esters such as ethyl acetate, amyl acetate, ethylene glycol acetate, diethylene glycol acetate, dibutyl maleate and diethyl succinate; alcohols such as methanol, n-hexanol, ethylene glycol, diethylene glycol, cyclohexanol and benzyl alcohol; ether alcohols such as ethylene glycol ethyl ether, ethylene glycol phenyl ether, diethylene glycol ethyl ether and diethylene glycol butyl ether; polar solvents such as dimethylformamide and dimethylsulfoxide; water, etc.
In addition, surfactants and other auxiliaries can be used for purposes of emulsification, dispersion, wetting, spreading, binding, regulation of disintegration, stabilization of the effective ingredient, improvement of fluidity, rust inhibition and the like on the compounds of the invention. Any of nonionic, anionic, cationic and amphoteric surfactants can be used as the surfactants, but usually nonionic and/or anionic compounds are used.
Examples of suitable nonionic surfactants include compounds obtained by addition polymerizing ethylene oxide with a higher alcohol such as lauryl alcohol, stearyl alcohol or oleyl alcohol; compounds obtianed by addition polymerizing ethylene oxide with an alkylphenol such as isooctylphenol or nonylphenol; compounds obtained by addition polymerizing ethylene oxide with an alkylnaphthol such as butylnaphthol or octylnaphthol; compounds obtained by addition polymerizing ethylene oxide with a higher fatty acid such as palmitic acid, stearic acid or oleic acid; higher fatty acid esters of polyhydric alcohols such as sorbitan and compounds obtained by addition polymerizing ethylene oxide with such a higher fatty acid ester; compounds obtained by block addition polymerizing ethylene oxide with propylene oxide; etc.
Examples of suitable anionic surfactants include alkyl sulfate ester salts such as sodium lauryl sulfate and amine salts of oleyl alcohol sulfuric acid ester; alkylsulfonate salts such as sodium 2-ethylhexenesulfonate; arylsulfonate salts such as sodium isopropylnaphthalenesulfonate, sodium methylenebisnaphthalenesulfonate, sodium ligninsulfonate and sodium dodecylbenzenesulfonate; etc.
Further, the herbicide of the invention can contain, for purposes of improving the properties of the preparations and enhancing its herbicidal effect, a high molecular compound such as casein, gelatin, albumin, glue, sodium alginate, carboxymethylcellulose, methyl-cellulose, hydroxyethylcellulose or polyvinyl alcohol and other auxiliaries.
The above carriers and various auxiliaries can be used alone or in combination according to their purposes taking the application forms and places of the preparations into account.
The content of the compound of the invention represented by the formula (I) amount of the active ingredient in the thus obtained preparations varies depending on the preparation form, but is usually 0.1 to 99% by weight, particularly preferably 1 to 80% by weight.
In case of dust, it usually contains 1 to 25% by weight of the effective ingredient compound and the remaining part is the solid carrier.
In case of wettable powder, it usually contains, for example, 25 to 90% by weight of the active ingredient compound and the remaining part is the solid carrier and the dispersing and wetting agents, and if necessary, a protective colloid agent and an antifoaming agent are added.
In case of granules, they usually contain, for example, 1 to 35% by weight of the active ingredient compound and most of the remaining part are the solid carrier, the surfactant, etc. The effective ingredient compound is either uniformly mixed with the solid carrier or uniformly adhering or adsorbed on the surface of the solid carrier, and the diameter of the grains is about 0.2 to 1.5 mm.
In case of emulsifiable concentrate, it usually contains, for example, 5 to 60% by weight of the active ingredient compound and the remaining part is the liquid carrier, and if necessary, a rust inhibitor is added.
In case of flowables, they usually contain, for example 5 to 50% by weight of the active ingredient compound and 3 to 10% by weight of the dispersing and wetting agents, and the remaining part is water, and if necessary, a protective colloid agent, an antiseptic, an antifoaming agent, etc. can be added.
The halogen-containing compounds of the invention represented by the formula (I) can be applied as such or in an optional preparation form as abovementioned.
The herbicide of the invention can be applied for the extermination on control of various weeds from before generation to growth phase growing in paddy fields and farmlands. The amount of the herbicide to be applied is on the order of 0.001 to 5 kg, preferably on the order of 0.01 to 1 kg per 1 ha as the amount of the compound represented by the formula (I) (the amount of the active ingredient), and can appropriately be selected and changed depending on the kind and growth stage of objective weeds, application place, application time, weather, etc.
Several embodiments of preparations wherein the compounds of this invention are used are denoted below. "Part" in the following preparation examples is based on weight.
PREPARATION EXAMPLE 1
Granules
______________________________________Compound number 1182b 5 partsBentonite 40 partsTalc 52 partsSodium lignisulfonate 2 partsPolyoxyethylene alkyl aryl ether 1 part______________________________________
The above components were sufficiently mixed, kneaded with the addition of a suitable amount of water and granuled by a granulator to obtain 100 parts of granules.
PREPARATION EXAMPLE 2
Wettable powder
______________________________________Compound number 1182b 20 partsDiatom earth 60 partsWhite carbon 15 partsSodium lignisulfonate 3 partsSodium dialkylnaphthalenesulfonate 2 parts______________________________________
The above components were mixed, and then uniformly mixed and pulverized by a jet mill to obtain 100 parts of wettable powder.
PREPARATION EXAMPLE 3
Emulsifiable concentrate
______________________________________Compound number 1182b 30 partsXylene 55 partsCyclohexanone 10 partsCalcium dodecylbenzenesulfonate 3 partsPolyoxyethylene alkyl aryl ether 2 parts______________________________________
The above components were uninformly mixed and dissolved to obtain 100 parts of an emulsion.
Herbicides using compounds of this invention could be each prepared according to the above preparation examples.
The halogen-containing compounds of the invention represented by the formula (I) are novel compunds not disclosed in literatures. The compounds of the invention represented by the formula (I) have their characteristic in that they take a structure wherein the .alpha.-halogenated carboxylic acid derivative part having a relatively simple structure and the pyrimidine ring or triazine ring part to which specific substituents bind at the 4-position and 6-position bind through an oxygen atom, sulfur atom or --OCH.sub.2 --, and it is considered that the excellent herbicidal effect is mainfested due to the structural characteristic.
The compounds and herbicide of this invention can exterminate and/or prevent various weeds from before generation to the growth phase which grow in agricultural lands. For example, the compounds and herbicide of the invention can exterminate and/or prevent weeds in paddy fields such as barnyardagrass (Echinochloa crus-galli), Japanese bulrush (Scirpus juncoides), "mizugayatruri"-(cyperus serotinus), monochoria (Monochoria vaginalis), common flase pimpernel (Lindernia pyxidaria), waterwort (Elatine triandra), indian toothcup (Rotala indica), needle spikerush (Eleocharis acicularis) and "urikawa" (segittaria pygmoea), and various weeds in farmlands such as crabgrass (Digitaria sanquinalis), giant foxtail (Setaria faberi), goosegrass (Eleusine indica), ricegrass paspalum (Paspalum orbiculare) water foxtail (Alopecurus aegualis), common chickweed (Stellaria media), various species of Polygonum, various species of Amaranthus, velvetleaf (Abutilon theophrasti), common lambsquarters (Chenopodium album), prickly sida (Sida spinosa), various species of Ipomoea, common cocklebur (Xanthium strumarium), common ragweed (Ambrosia artemisialfolia), sheherd'spurse (Capsella bursa-pastoris), flexuous bittercress (Cardamine flexuosa), hairy beggarticks (Bidens pilosa), catchweed bedstraw (Galium aparine), wild mustard (Brassica kaber), various species of Ipomoea, jimsonweed (Datura stramonium), wild sunflower and wild buckwheat (Polygonum convolvulus). Further, the compounds and herbicide of this invention can be used not only in paddy fields and farmlands but also in fruit farms, lawns, and non-crop lands.
Moreover, the compounds of this invention have selectivity on some kinds of crops, and particularly do not give such phytotoxicity as practically becomes a problem on crops such as cotton, soybean and maize.
The herbicidal effects of the compounds and herbicide of this invention and described below according to test examples.
TEST EXAMPLE 1
Foliar application test in a upland field
Plowed field soil was packed into four-sided port (30.times.30.times.12 cm), a predetermiend amount each of the seeds of the various crops and various weeds shown in Table 17 were sown respectively, and the respective plants were grown in a greenhouse up to 1.5 to 3 leaf stage. Wettable powders were prepared according to Preparation example 2 using the compounds of this invention shown in Table 17 respectively. A dilution of each wettable powder with water was evenly applied on the foliages of each plant in the application amount corresponding to 500 1/ha so that the active ingredient amount indicated in Table 17 was given. 21 days after the application, herbicidal effects on the various weeds and the degree of phytotoxicity on the various crops were evaluated according to the following criterion. The results are shown in Table 17.
______________________________________ Herbicidal effect: Phytotoxicity on crop: weeding rate (%) phytotoxicity rate (%) based on the non- based on the non-Rating treated group control group______________________________________0 0 the same as left1 above - 102 above - 203 above - 304 above - 405 above - 506 above - 607 above - 708 above - 809 above - 9010 above - 100 (withered)______________________________________
TABLE 17__________________________________________________________________________Foliar application test in upland field Amount ofCom- active Herbicidal effect Phytotoxicitypound ingredient barnyard giant slender velvet- tall morning- cock- wild wild soy-No. (g/ha) grass foxtail Amaranth leaf glory lebur mustard sunflower maize bean cotton__________________________________________________________________________1004b 50 10 10 10 10 10 10 10 10 -- -- 04228b 50 10 10 10 10 10 10 10 10 -- -- 01182b 50 10 10 10 10 10 10 10 10 0 -- --1184b 50 10 9 10 10 9 10 10 10 0 -- --1411b 50 -- -- 10 10 9 10 9 10 1 -- --2039 50 10 10 10 10 10 10 10 10 -- -- 02057b 50 10 10 10 10 10 10 10 10 0 -- --3003b 50 10 10 10 10 10 10 10 10 0 0 01187b 50 10 9 10 10 10 10 10 10 0 -- --1234b 50 10 9 10 10 10 10 10 10 1 -- --4512b 50 10 9 10 10 10 10 10 10 1 -- --__________________________________________________________________________
TEST EXAMPLE 2
Pre-emergence soil application test in upland filed
Plowed field soil was packed into four-sided ports (30.times.30.times.12 cm), a predetermined amount each of the seeds of the various crops and various weeds shown in Table 18 were sown respectively, and covered with the soil so that the height of the covering soil became 1 cm. Wettable powders were prepared according to Preparation example 2 using the compounds of this invention shown in Table 18 respectively. A dilution of each wettable powder was evenly applied on the soil surface in the application amount corresponding to 500 1/ha so that the active ingredient amount indicated in Table 18 was given. 21 days after the application, herbicidal effects on the various weeds and the degree of phytotoxicity on the various crops were evaluated according to the criterion in Test example 1. The results are shown in Table 18.
TABLE 18__________________________________________________________________________(Prior-germinating soil application test in upland field) Amount ofCom- active Herbicidal effect Phytotoxicitypound ingredient barnyard giant slender velvet- tall morning- cock- wild wild soy-No. (g/ha) grass foxtail Amaranth leaf glory lebur mustard sunflower maize bean cotton__________________________________________________________________________1004b 100 10 10 10 10 10 10 10 10 -- 0 01006b 100 10 10 10 10 10 10 10 10 -- 0 01010b 100 10 10 10 10 10 10 10 10 -- 0 04228b 100 10 10 10 10 10 10 10 10 -- 0 04230b 100 -- -- 10 10 10 10 10 10 1 0 02039 100 10 10 10 10 10 10 10 10 0 0 02057b 100 10 10 10 10 10 10 10 10 -- 0 07004b 100 10 10 9 10 10 9 10 10 -- 1 --2346b 100 10 10 10 10 9 9 10 -- -- 1 --__________________________________________________________________________
TEST EXAMPLE 3
Nonselective foliar application test
Plowed field soil was packed into foursided pots (30.times.30.times.12 cm), a predetermined amount each of the seeds of the various weeds shown in Table 19 were sown respectively, and the respective plants were grown in a greenhouse up to 1.5 to 3 leaf stage. Wettable powders were prepared according to Preparation example 2 using the compounds of this invention shown in Table 19 respectively. A dilution of each wettable powder with water to which a spreader Surfactant WK (produced by Maruwa Biochemical Co., Ltd.) was added so that the concentraton became 0.25% was evenly applied on the foliages of each plant in the application amount corresponding to 500 1/ha so that the active ingredient amount indicated in Table 19 was given. 21 days after the application, herbicidal effects on the various weeds were evaluated according to the following criterion. The results are shown in Table 19.
______________________________________Evaluation criterion (11 stages) Herbicidal effect: weeding rate (%) based on the non-Rating treated group______________________________________0 01 above - 102 above - 203 above - 304 above - 405 above - 506 above - 607 above - 708 above - 809 above - 9010 above - 100 (withered)______________________________________
TABLE 19__________________________________________________________________________(Nonselective foliar application test) amount ofCom- activepound ingredient barnyard- giant slender velvet- tall morning- cock- wild wild jimson- hairyNo. (g/ha) grass foxtail Amaranth leaf glory lebur mustard sunflower weed beggarticks__________________________________________________________________________1003b 50 10 9 10 10 10 10 10 10 10 101003b2 50 10 10 10 10 10 10 10 10 10 101002b 50 10 10 10 10 10 10 10 10 10 101246b 50 10 9 10 10 10 10 10 10 10 101180b 50 10 10 10 10 10 10 10 10 10 10__________________________________________________________________________
TEST EXAMPLE 4
Nonselective pre-emergence soil application test
Plowed field soil was packed into foursided pots (30.times.30.times.12 cm), a predetermined amount each of the seeds of the various weeds shown in Table 20 were sown respectively, and covered with the soil so that the height of the covering soil became 1 cm. Wettable powders were prepared according to Preparation example 2 using the compounds of this invention shown in Table 20. A dilution of each wettable powder was evenly applied on the soil surface in the application amount coresponding to 500 1/ha so that the active ingredient amount indicated in Table 20 was attained. 21 days after the application, hervicidal effects on the various weeds were evaluated according to the criterion in Test example 3. The results are shown in Table 20.
TABLE 20__________________________________________________________________________(Nonselective prior-germinating soil application test)Com- amount ofpound active barnyard- giant slender velvet- tall morning- cock- wild common hairyNo. ingredient grass foxtail Amaranth leaf glory lebur mustard ragweed beggarticks__________________________________________________________________________1002b 100 10 10 10 10 10 10 10 10 104035b 100 10 10 10 10 10 9 10 10 104048b 100 10 10 10 10 10 9 10 10 104071b 100 10 10 10 10 10 9 10 10 104079b 100 10 10 10 10 10 10 10 10 105156b 100 10 10 10 10 10 8 10 10 10__________________________________________________________________________

Number	Date	Country
2-193807	Jul 1990	JPX
2-193808	Jul 1990	JPX
3-50340	Feb 1991	JPX
3-50523	Feb 1991	JPX
3-118095	Apr 1991	JPX
3-128188	May 1991	JPX
3-128208	May 1991	JPX

Number	Date	Country
249708	Dec 1987	EPX
287079	Oct 1988	EPX
315889	May 1989	EPX
0346789	Dec 1989	EPX
0431707	Jun 1991	EPX
0439243	Jul 1991	EPX
3126691	Jun 1989	JPX
0031266	Feb 1991	JPX

Halogen-containing compounds, herbicidal composition containing the same as an active ingredient, and intermediary compounds therefor

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