Abstract:
Antifungal carbinols, particularly α-styryl carbinols, and the corresponding epoxy carbinols are provided. These carbinol compounds have the formula: ##STR1## or a pharmaceutically or agriculturally suitable salt thereof wherein E is a bond or an oxygen atom with the proviso that when E is oxygen; R, R 1  are not halogen; and 
     L, A, B, Q, R 2 , R 3 , R 4  and n are as defined in the specification.

Description:
CROSS-REFERENCE 
     This application is a continuation-in-part of copending application Ser. No. 042,541, filed Apr. 29, 1987, which in turn is a continuation-in-part of application Ser. No. 877,525, filed June 23, 1986, both abandoned. 
    
    
     FIELD OF THE INVENTION 
     This invention relates to antifungal carbinols, particularly α-styryl carbinols, and the corresponding epoxy carbinols, pharmaceutical and agricultural compositions containing them, processes for preparing them and methods of using them as antifungal agents in mammals and plants. 
     BACKGROUND INCLUDING PRIOR ART 
     Systemic fungal infections are of increasing importance because of continued and expanded use of immunosuppressive therapies, antimicrobial therapies and indwelling catheters. Currently there are limited therapies available to treat such fungal infections. Amphotericin B remains the drug of choice because it has the widest spectrum of antifungal activity of any systemic antifungal drug, however its utility is limited by its toxicity. Because of the potential seriousness of its toxic effects, intravenous use of amphotericin B is primarily for patients with progressive, potentially fatal infections in which the patient is hospitalized during the course of therapy. Thus, there is a continuing need to develop safer and more effective drugs which are useful for the treatment of fungal infections. 
     Plant pathogenic fungi and other disease incitants also cause extensive losses in crops annually. While there are commercially available materials used to control many plant diseases, further improvement in this art is needed if full food and fiber production is to be realized. 
     There are a large number of patent and literature reference in the area of azole antifungal drugs and plant disease control agents. Most pertinent to the α-styryl carbinol compounds of this invention are the following references: 
     B. Sugavanam in U.S. Pat. No. 4,507,140 issued Mar. 26, 1985 discloses fungicidal or plant growth regulating β-styryl triazoles or imidazoles, amongst others of the formula: ##STR2## where R 1  is CH═CH--X; --C.tbd.C--X or --CH 2  --CH 2  --X; 
     X is substituted aryl, aralkyl, or heterocycle; 
     R 2  is alkyl, cycloalkyl, or optionally substituted aryl; 
     Z is OR 3  ; 
     R 3  is H, acetyl; 
     Y is --N-- or --CH--. 
     German Patent No. 3,018,865, published May 16, 1980 discloses antimycotic agents of the formula: ##STR3## where amongst others R is alkyl, optionally substituted cycloalkyl or optionally substituted phenyl radical; 
     X is N, or a CH group; 
     Y is --OCH 2  --, --CH 2  CH 2  -- or CH═CH; 
     Z is halogen, alkyl, cycloalkyl, alkoxy, alkythio, etc. 
     German Patent No. 3,314,548-A, published Apr. 21, 1983 discloses substituted 1-hydroxy-ethyl-triazole derivatives of the formula: ##STR4## where amongst others R is alkyl, cycloalkyl or phenyl optionally substituted; 
     X is --OCH 2  --, --SCH 2  --, --(CH 2 ) p  or --CH═CH--; 
     Z is halogen, alkyl, alkoxy, alkylthio, haloalkyl, haloalkoxy, or haloalkylthio; 
     m and p are 0, 1 and 2. 
     The compounds are antimycotics for treating dermatophytomycoses and systemic mycoses caused e.g., by Candida sp., Aspergillus sp., Trichophyton sp. 
     The above three references, which pertain to β-styryl azoles, are believed to be the most relevant. The β-styryl azole analog of one of the preferred compounds of the instant invention was prepared and found to be significantly less active. 
     European Patent Application No. 114,487 which published Aug. 1, 1984 discloses azolylethanol derivatives of the formula: ##STR5## 
     Where amongst others R 1  and R 2  which may be the same or different are hydrogen, alkyl, cycloalkyl, alkenyl, heterocyclyl aryl, or aralkyl optionally substituted; W is N or CH; and X is C═O. The compounds have fungicidal activity and plant growth regulating activity. 
     European Patent No. 117,578-A, published Feb. 23, 1984 discloses heterocyclic-hydroxy-alkyl alkyl ketone(s) and analogues of the formula: ##STR6## where A is CO amongst others; 
     Q is imidazoyl or 1H-- or 4H-1,2,4-triazol-1-yl; 
     R 1  is H, 1-5C alkyl, or 1-8C acyl; 
     R 2  and R 3  are 1-5C alkyl, 3-6C cycloalkyl, 2-6C alkenyl, benzyl (optionally substituted by 1-3 halogen), pyridyl, furyl, thienyl, or phenyl optionally substituted by 1-3 halogen, 1-3 alkyl, or 1-3C alkoxy. 
     Belgian Patent No. 900,594-A published Sept. 22, 1983 discloses 1-phenyl-1-azolyl-hydroxyethyl cycloalkane derivatives of the formula: ##STR7## where R 1  and R 2  ═H, halo, NO 2 , lower alkyl, alkenyl, alkynyl, alkoxy or alkylthio (all optionally substituted by 1 or more halo), or optionally substituted phenyl or phenoxy; 
     R 3  =H or lower alkyl; 
     R 4  and R 5  =H or halo; 
     Y=CH or N; 
     A=2-7C alkylene; 
     n=0 or 1. 
     The compounds are useful as agricultural fungicides and antimycotics. 
     None of the cited references nor any known references suggest the novel antifungal compounds of this invention. 
     SUMMARY OF THE INVENTION 
     According to the present invention compounds are provided having the formula: ##STR8## or a pharmaceutically or agriculturally suitable salt thereof wherein E is a bond or an oxygen atom with the proviso that when E is oxygen; R, R 1  are not halogen; 
     A is perfluoroalkyl of 1-8 carbon atoms, N(CH 3 ) 2 , OH, naphthyl optionally substituted with a total of 1-3 substituents each of which is independently selected from halogen and CF 3 , ##STR9##  optionally substituted with 1 or 2 methyl groups, phenyl optionally substituted with a total of 1-3 substituents each of which is independently selected from: 
     halogen, alkyl of 1-4 carbon atoms, haloalkyl of 1-4 carbon atoms, alkoxy of 1-4 carbon atoms, and with no more than one group selected from: 
     haloalkoxy of 1-4 carbon atoms, CN, CO 2  R 14 , CH═NOR 14 , S(O) m  R 5 , R 6 , 2-,3-, or 4-pyridyl or an N-oxide thereof, imidazol-1-yl, 1,2,4-triazol-1-yl, and ##STR10## optionally substituted with 1 or 2 methyl groups,  or a heterocycle selected from imidazol-1-yl, 1,2,4-triazol-1-yl, 2-or 3-thienyl, and 2-,3-, or 4-pyridyl or an N-oxide thereof, optionally substituted with one or two substituents each of which is independently selected from: 
     halogen, alkyl of 1-4 carbon atoms, CF 3 , alkoxy of 1-4 carbon atoms, haloalkoxy of 1-4 carbon atoms, and S(O) m  R 5  ; 
     B is alkyl of 1-8 carbon atoms, naphthyl, biphenyl, ##STR11##  perfluoralkyl of 1-8 carbon atoms, phenyl optionally substituted with 1-3 substituents each of which is independently selected from: halogen, alkyl of 1-4 carbon atoms, haloalkyl of 1-4 carbon atoms, alkoxy of 1-4 carbon atoms, and with no more than one group selected from haloalkoxy of 1-4 carbon atoms, CN, CO 2  R 14 , CH═NOR 14 , S(O) m  R 5 , 2-,3-,4-pyridyl or an N oxide thereof, 
      benzyl optionally substituted on the phenyl ring with halogen or alkyl of 1-4 carbon atoms, or optionally α-substituted with 1 or 2 methyl groups, or 
      a heterocycle selected from 2-or 3-thienyl, and 2-,3-, or 4-pyridyl, said heterocycles being optionally substituted with one or two substituents each of which is independently selected from: 
     halogen, alkyl of 1-4 carbon atoms, haloalkoxy of 1-4 carbon atoms, CF 3 , or S(O) m  R 5  ; 
     Q is H, halogen, S(O) m  R 11 , ##STR12##  CO 2  R 13 , SCN, SSR 12 , or SH or its corresponding disulfide, provided however that when Q is other than H, then n is O, R, R 1 , and R 4  are independently H or CH 3 , R 3  is H, and A and B are each phenyl optionally substituted with from 1-3 substituents each of which is independently halogen, CH 3 , CF 3 , OCH 3  or S(O) m  R 5  ; 
     L is CH or N with the proviso that when L=CH then Q=H; 
     n is 0-4 with the proviso that when A is ##STR13##  N(CH 3 ) 2 , or OH, then n is other than O; m each occurrence is 0, 1 or 2; 
     X is C, NR 10 , or O; 
     R and R 1  independently are H, alkyl of 1-4 carbon atoms, halogen, or phenyl, or taken together form cycloalkyl of 3-7 carbon atoms; 
     R 2  is H, allyl, propargyl, alkyl of 1-4 carbon atoms, ##STR14##  or haloalkyl of 1-4 carbon atoms; R 3  and R 4  independently are H, F, or alkyl of 1-4 carbon atoms; 
     R 5  is alkyl of 1-4 carbon atoms; 
     R 6  is phenyl optionally substituted with a total of 1-3 substituents each of which is independently selected from halogen and CF 3  ; 
     R 7  is alkyl of 1-4 carbon atoms, phenyl, or benzyl; 
     R 8  and R 9  independently are H, alkyl or 1-4 carbon atoms, phenyl or benzyl; 
     R 10  is H, alkyl of 1-4 carbon atoms, or acetyl; 
     R 11  is alkyl of 1-4 carbon atoms, haloalkyl of 1-2 carbon atoms, CH 2  CN, CH 2  SCN, CH(CH 3 )CN, CH 2  CO 2  CH 3 , or CH 2  CO 2  CH 2  CH 3  ; 
     R 12  is alkyl of 1-4 carbon atoms, allyl, phenyl optionally substituted with 1-2 substituents each of which is independently halogen, CH 3 , or OCH 3 , or benzyl optionally substituted with 1-2 substituents each of which is independently halogen, CH 3 , or OCH 3  ; 
     R 13  is H, or alkyl or 1-4 carbon atoms; and 
     R 14  is alkyl of 1-4 carbon atoms. 
     Also provided are pharmaceutical compositions comprising a suitable pharmaceutical carrier and a therapeutically effective amount of a compound of Formula (I) or its pharmaceutically suitable salt and methods of using the compounds of Formula (I) as antifungal agents. 
     This invention further provides agricultural compositions comprising a compound of Formula (I) or its agriculturally suitable salt together with an agriculturally acceptable diluent or carrier and a method of controlling fungal diseases in plants. 
     Certain compounds of this invention are useful as herbicides and plant growth regulants. This invention, therefore, also relates to the herbicidal composition of these compounds and their method of use as herbicides. 
     The herbicidal compounds are those of Formula (I) wherein: 
     E is a bond; 
     L is N; 
     A is perfluoralkyl of 1-4 carbon atoms, naphthyl optionally substituted with a total of 1-2 substituents each of which is independently selected from halogen and CF 3 , ##STR15##  optionally substituted with 1 or 2 methyl groups, phenyl optionally substituted with a total of 1-3 substitutents each of which is independently selected from: 
     halogen, alkyl or 1-3 carbon atoms, haloalkyl of 1-3 carbon atoms, alkoxy of 1-3 carbon atoms, and with no more than one group selected form: 
     haloalkoxy of 1-3 carbon atoms, CN, CO 2  R 14 , CH═NOR 14 , R 6 , 2-,3-,or 4-pyridyl, or an N-oxide thereof, imidazol-1-yl, 1,2,4-triazol-1-yl, and ##STR16## optionally substituted with 1 or 2 methyl groups,  or a heterocycle selected from imidazol-1-yl, 1,2,4-triazol-1-yl, 2-or 3-thienyl, and 2-,3-, or 4-pyridyl, said heterocycles being optionally substituted with one or two substituents each of which is independently selected from: 
     halogen, alkyl of 1-2 carbon atoms, and CF 3  ; 
     B is alkyl of 1-4 carbon atoms, naphthyl, perfluoroalkyl of 1-4 carbon toms, phenyl optionally substituted with 1-2 substituents each of which is independently selected from: halogen, alkyl of 1-3 carbon atoms, haloalkyl of 1-3 carbon atoms, alkoxy of 1-3 carbon atoms, and with no more than one group selected from haloalkoxy of 1-3 carbon atoms, and CN, 
     benzyl optionally substituted on the phenyl ring with halogen or alkyl of 1-3 carbon atoms, or optionally α-substituted with 1 or 2 methyl groups, or 
     a heterocycle selected from 2-or 3-thienyl, and 2-,3-,or 4-pyridyl, said heterocycles being optionally substituted with one or two substituents each of which is independently selected from: 
     halogen, alkyl of 1-3 carbon atoms, or CF 3  ; 
     Q is H, halogen, S(O) m  R 11 , ##STR17##  CO 2  R 13 , SCN, SSR 12 , or SH or its corresponding disulfide, provided however that when Q is other than H, then n is O, R, R 1 , and R 4  are independently H or CH 3 , R 3  is H, and A and B are each phenyl optionally substituted with from 1-3 substituents each of which is independently halogen, CH 3 , CF 3 , or OCH 3  ; 
     n is 0-2 with the proviso that when A is ##STR18## then n is other that O; m each occurrence is 0, 1 or 2; 
     X is C, NR 10 , or O; 
     R and R 1  independently are H, alkyl of 1-2 carbon atoms, halogen, or phenyl, or taken together form cycloalkyl of 3-6 carbon atoms; 
     R 2  is H, allyl, propargyl, alkyl of 1-2 carbon atoms, ##STR19##  or haloalkyl of 1-4 carbon atoms; R 3  and R 4  independently are H, F, or alkyl of 1-2 carbon atoms; 
     R 6  is phenyl optionally substituted with a total of 1-3 substituents each of which is independently selected from halogen and CF 3  ; 
     R 7  is alkyl of 1-2 carbon atoms, phenyl or benzyl. 
     R 8  and R 9  independently are H, alkyl of 1-2 carbon atoms, phenyl or benzyl; 
     R 10  is H, alkyl of 1-2 carbon atoms, or acetyl; 
     R 11  is alkyl of 1-2 carbon atoms, haloalkyl of 1-2 carbon atoms, CH 2  CN, CH 2  SCN, CH(CH 3 )CN, CH 2  CO 2  CH 3 , or CH 2  CO 2  CH 2  CH 3  ; 
     R 12  is alkyl of 1-2 carbon atoms, allyl, phenyl optionally substituted with 1-2 substituents each of which is independently halogen, CH 3 , or OCH 3 , or benzyl optionally substituted with 1-2 substituents each of which is independently halogen, CH 3 , or OCH 3  ; and 
     R 13  is H, or alkyl of 1-2 carbon atoms. 
     Further provided are processes for the preparation of the aforesaid compounds, which processes are described hereinafter. 
     Additionally provided are novel intermediates having the formulas (II) and (IIa) shown below: ##STR20## wherein A, B, R, R 1 , R 3 , R 4  and n are as defined above, except that R 3 , R 4  are not F and not both alkyl. 
     PREFERRED EMBODIMENTS 
     Preferred compounds are the α-styryl compounds of formula (I) (E is a bond) where: 
     (1) n=0, or 1; and/or 
     (2) R 3  and R 4  independently are H, CH 3 , or F. 
     More preferred compounds are preferred compounds where: 
     (1) A, and B independently are phenyl optionally substituted with from 1-3 substituents each of which is halogen, alkyl or 1-4 carbon atoms, haloalkyl or 1-4 carbon atoms, alkoxy of 1-4 carbon atoms, or S(O) m  R 5  ; and/or 
     (2) n=0; and/or 
     (3) R and R 1  independently are H, CH 3  or halogen; and/or 
     (4) R 2  =H, alkyl of 1-4 carbon atoms, allyl, or propargyl; and/or 
     (5) Q is H, I, SH. 
     Most preferred compounds are more preferred compounds where: 
     (1) A and B independently are phenyl optionally substituted with from 1-3 halogen atoms, CH 3 , OCH 3 , CF 3 , or SCH 3  ; and/or; 
     (2) R, R 1 , R 2 , R 3 , R 4  and Q are all H. 
     Specifically preferred because of their biological activity are the following compounds or salts thereof: 
     (a) 2-(4-Fluorophenyl)-3-phenyl-1-(1H-1,2,4-triazol-1-yl)-3-buten-2-ol; and the (S) enantiomer thereof. 
     (b) 2,3-Bis(4-fluorophenyl)-1-(1H-1,2,4-triazol-1-yl)-3-buten-2-ol; and the (S) enantiomer thereof. 
     (c) 2-(2,4-Dichlorophenyl)-3-(4-chlorophenyl)-1-(1H-1,2,4-triazol-1-yl)-3-buten-2-ol; and the (S) enantiomer thereof. 
     (d) 2-(4-Chlorophenyl)-3-(2-chlorophenyl)-1-(1H-1,2,4-triazol-1-yl)-3-buten-2-ol; and the (S) enantiomer thereof; 
     (e) 2-(2,4-Dichlorophenyl)-3-(3-fluorophenyl)-1-(1H-1,2,4-triazol-1-yl)-3-buten-2-ol; and the (S) enantiomer thereof. 
     (f) 2-(2-Chlorophenyl)-3-(2-chlorophenyl)-1-(1H-1,2,4-triazol-1-yl)-3-buten-2-ol; and the (S) enantiomer thereof. 
     (g) 2-(2,4-Dichlorophenyl)-3-(3-chlorophenyl)-1-(1H-1,2,4-triazol-1-yl)-3-buten-2-ol; and the (S) enantiomer thereof. 
     (h) 2-(4-Fluorophenyl)-3-(4-trifluoromethylphenyl)-1-(1H-1,2,4-triazol-1-yl)-3-buten-2-ol; and the (S) enantiomer thereof. 
     (i) 2-(2,4-Dichlorophenyl)-3-phenyl-1-(1H-1,2,4-triazol-1-yl)-3-buten-2-ol; and the (S) enantiomer thereof. 
     (j) 2-(3,4-Dichlorophenyl)-3-(4-fluorophenyl)-1-(1H-1,2,4-triazol-1-yl)-3-buten-2-ol; and the (S) enantiomer thereof. 
     (k) 2-(4-Chlorophenyl)-3-(3-chlorophenyl)-1-(1H-1,2,4-triazol-1-yl)-3-buten-2-ol; and the (S) enantiomer thereof. 
     (l) 2-(4-Fluorophenyl)-3-(2,4-difluorophenyl)-1-(1H-1,2,4-triazol-1-yl)-3-buten-2-ol; and the (S) enantiomer thereof. 
     (m) 2-(2,4-Difluorophenyl)-3-(2-chlorophenyl)-(1H-1,2,4-triazol-1-yl)-3-buten-2-ol; and the (S) enantiomer thereof. 
     (n) 2-(2,4-Dichlorophenyl)-3-(2-chlorophenyl)-1-(1H-1,2,4-triazol-1-yl)-3-buten-2-ol; and the (S) enantiomer thereof. 
     (o) 2-(2,4-Difluorophenyl)-3-phenyl)-1-(1H-imidazol-1-yl)-3-buten-2-ol; and the (S) enantiomer thereof. 
     (p) 2-(2,4-Difluorophenyl)-3-(4-fluorophenyl)-1-(1H-imidazol-1-yl)-3-buten-2-ol; and the (S) enantiomer thereof. 
     (q) 2-(2,4-Difluorophenyl)-3-(2-chlorophenyl)-1-(1H-imidazol-1-yl)-3-buten-2-ol; and the (S) enantiomer thereof. 
     (r) 2-(2,4-Difluorophenyl)-3-phenyl-1-(1H-1,2,4-triazol-1-yl)-3-buten-2-ol; and the (S) enantiomer thereof. 
     (s) 2-(2,4-Difluorophenyl)-3-(4-fluorophenyl)-1-(1H-1,2,4-triazol-1-yl)-3-buten-2-ol; and the (S) enantiomer thereof. 
     (t) 2-(2-Fluorophenyl)-3-(4-fluorophenyl)-1-(1H-1,2,4-triazol-1yl)-3-buten-2-ol; and the (S) enantiomer thereof. 
     (u) 2-(2-Fluorophenyl)-3-(4-chlorophenyl)-1-(1H-1,2,4-triazol-1-yl)-3-buten-2-ol; and the (S) enantiomer thereof. 
     (v) 2-(2,4-Difluorophenyl)-3-(4-chlorophenyl)-1-(1H-1,2,4-triazol-1-yl)-3-buten-2-ol; and the (S) enantiomer thereof. 
     (w) 2-(2-Chlorophenyl)-3-(4-fluorophenyl)-1-(1H-1,2,4-triazol-1-yl)-3-buten-2-ol; and the (S) enantiomer thereof. 
     (x) 2-(4-Chlorophenyl)-3-phenyl-1-(1H-1,2,4-triazol-1yl)-3-buten-2-ol; and the (S) enantiomer thereof. 
     All of the compounds within the scope of this invention are active in either pharmaceutical or agricultural fungicidal assays or agricultural herbicidal assays. Thus, it should be recognized that there are compounds which are not always active in both assays as is shown with some compounds in the Examples. Of the above listed specifically preferred compounds, compounds (a)-(r) or their salts are preferred for pharmaceutical uses and compounds (r)-(x) or their salts are preferred for agricultural uses. 
    
    
     DETAILED DESCRIPTION OF THE INVENTION 
     Synthesis 
     The novel compounds of Formula (I) can be prepared using the reactions and techniques described in this section. The reactions are usually performed in a solvent appropriate to the reagents and materials employed, and suitable for the transformation being effected. In some cases functional groups on the starting materials may need to be protected by standard protecting groups reported in the chemical literature which are well known to one skilled in the art. 
     In some cases, substituents on the starting materials may be incompatible with some of the reaction conditions required in some of the methods described. Such restrictions to the substituents which are compatible with the reaction conditions will be readily apparent to one skilled in the art and alternative methods described must then be used. 
     The compounds of the present invention can contain at least one chiral center and as such can exist as two individual isomers or as a racemic mixture of both. This invention relates to the (S) isomer, as well as to racemic mixtures containing both isomers. 
     For the purposes of this invention, the (S)-isomer of compounds of Formula (I) is intended to mean compounds of the configuration depicted: ##STR21## 
     When a single chiral center is present the resolution can be performed by reacting the compound with a chiral strong acid (e.g. substituted camphorsulfonic acids) in a suitable solvent (e.g. acetonitrile) or mixture of solvents (e.g. 3/1 etheracetone). This reaction is carried out at a temperature between 25° C. to 100° C., preferably at the reflux temperature of the solvent(s) employed. The reaction produces two diastereomeric adducts that can be separated by fractional crystallization. The adduct can then be cleaved in basic medium (e.g. sat. NaHCO 3 , sat. Na 2  CO 3 ) to give the resolved product. 
     The compounds of Formula I, where E is a bond, R 2  and Q are H and R 3 , R 4  are not F and not both alkyl, can be prepared by contacting an oxirane of Formula (II) or a halohydrin of Formula (IIa), or a mixture of (II) or (IIa) with imidazole or triazole or a corresponding alkali metal salt (preferably the Na +  or K +  salt) in a suitable solvent (Scheme I). ##STR22## 
     When imidazole or triazole is used, an acid acceptor, such as potassium carbonate, sodium methoxide or sodium hydride, is added to the reaction mixture. Suitable inert solvents include polar, aprotic solvents such as dimethylformamide (DMF), dimethylsulfoxide (DMSO) and ethereal solvents such as tetrahydrofuran (THF). Non-polar solvents, such as toluene, may be used if a phase transfer catalyst, such as tetrabutylammonium bromide, is added. The reaction is carried out at a temperature in the range of 10° to 150° C., preferably from 50° to 120° C., for a period of 0.25 to 24 hours. It is recognized that varying amounts of the 4H-1,2,4-triazol-4-yl isomers of Formula (I) may be formed when triazole is used in the above reaction. The isomers can be separated, if desired, using standard separation techniques, e.g., chromatography. 
     The 4H-1,2,4-triazol-4-yl isomers of Formula (I) can be converted to the compounds of Formula (I) by isomerization with base as described in EP No. 143384A2, or by heating with 2-100 mol % of oxiranes of Formula (II), halohydrins of Formula (IIa), reactive alkyl or benzyl bromides or iodides, such as benzyl bromide or methyl iodide, or commercial oxiranes such as styrene oxide, at temperatures of 100°-200° C.; preferably, in a polar aprotic solvent such as DMF, or a non-polar solvent such as one of the xylenes. 
     The oxiranes of Formula (II) can be prepared using one or both of the following methods; (Scheme 2). In the first, vinyl organometallic reagents, e.g., vinyl Grignard reagents, of Formula (III) are allowed to react with haloketones of Formula (IV) in the presence of ethereal solvents, such as THF or diethyl ether, at a temperature ranging from -90° to 60° C., preferably -10° to 50° C., for 0.5 to 24 hours. Depending on the reaction conditions and the value of X in the haloketone starting material (IV), the product may be an oxirane (II), a halohydrin (IIa) or a mixture of (II) and (IIa). If desired, the halohydrins (IIa) may be converted to oxiranes (II) by treatment with base, e.g., potassium hydride (KH), in a solvent such as THF. ##STR23## 
     In the second method, keto-oxiranes of formula (V) are olefinated with, for example, Wittig reagents, which provide epoxy-olefins of Formula (II). 
     Unsaturated ketones of Formula (VII) can be converted to epoxy-olefins (II) by treatment with dimethylsulfonium methylide. The enones (VII) can be prepared by treatment of ketones of Formula (VI) with carbonyl compounds and appropriate catalysts (Scheme 3). ##STR24## 
     Unsaturated ketones of Formula (VIII) can be converted to epoxyketones (V) using basic hydrogen peroxide. Olefination of (V), as described above, provides epoxyolefins (II) (Scheme 4). ##STR25## 
     The vinyl organometallics of Formula (III) are prepared using standard procedures from the corresponding chlorides, bromides or iodides. The haloolefins, the haloketones of Formula (IV), the ketooxiranes of Formula (V) and the ketones of Formula (VI) are known, or can be prepared using methods known to one skilled in the art. 
     Compounds of Formula (I) can also be prepared by olefination of ketones (IX) with, for example, Wittig reagents (Scheme 5). Ketones of Formula (IX) where R 2 , R 3  and R 4  =H are known (EP No. 117578A). ##STR26## 
     Compounds of general Formula (I) where R 3  and/or R 4  ≠H can be made as shown in Scheme 6 by reacting ketones of general Formula (X) with the appropriate organometallic reagent (e.g. Grignard reagent, organolithium reagent). The ketones (X) are prepared by conventional methods from the corresponding α-haloketones (IV) (see e.g. EP No. 0044605, UK No. 2099818A, UK No. 146224, EP No. 1337718, and EP No. 0153803). ##STR27## 
     Compounds of Formula (I) where A=(heterocycle)-phenyl can be prepared from appropriately substituted precursors using the methods described above, or by using substitution reactions on (I) wherein A is halophenyl. For example, compounds of Formula (I) where A is (pyridyl)phenyl can be prepared by treatment of (I), wherein A is bromophenyl or iodophenyl, with the appropriate pyridylstannanes in the presence of palladium catalysts (see Tetrahedron Letters, 27, 4407, 1986). Copper assisted displacement of halogen (Tetrahedron, 40, 1433, 1984) with heterocyclic nucleophiles provides compounds of Formula (I) where A is for example 1-imidazolylphenyl. 
     In some cases, it may be desirable to begin with compounds of Formula I, wherein A is aminophenyl, and construct the heterocyclic ring using X(CH 2  CH 2  Cl) 2  (see ES 8603-473-A). 
     The compounds of Formula (I) where Q≠H and L=N can be prepared as shown in Scheme 7. Metalation of (I), Q=H with strong base provides the 5-metalated triazoles (Ia) (See Heterocycles, 23, 1645-1649, 1985). When R 2  is H, 2 equivalents of base are required. Typical conditions involve treatment of a solution of (I) in THF at -70° with n-butyllithium for 15-30 minutes. Where the metalated triazole (Ia) is less soluble than (I), the addition of co-solvents, such as dimethylpropyleneurea (DMPU) may be beneficial. ##STR28## 
     The treatment of (Ia) with electrophiles gives a wide variety of (I) where Q≠H. Electrophiles of relevance to the present invention include halogenating agents, sulfur, disulfides, carbon dioxide, dimethylamides and sulfur dioxide followed by alkyl halides. Subsequent functionalization, using methods known to one skilled in the art, provide other compounds of Formula (I) wherein Q≠H. For example, the treatment of (I), where Q is SH with isocyanates or phthalimidosulfides provides thiocarbamates (I); ##STR29## or disulfides (I; Q=SSR 12 ), respectively. 
     The compounds of general Formula (I) where E is oxygen can be prepared by oxidation of compounds of general Formula (I) where E is a bond provided that R, R 1  ≠halogen using methods described in the literature (Scheme 8): ##STR30## 
     Suitable reagents which can effect this oxidation, depending on the nature of the substituents, include peracids such as m-chloroperbenzoic acid; hydroperoxides such as tert-butyl hydroperoxide in the presence of an appropriate catalyst such as vanadium acetonylacetonate; or hydrogen peroxide. Alternatively, the transformation can be effected by first forming the halohydrin with a hypohalous acid such as hypobromous acid and then reacting the intermediate halohydrin with a proton acceptor such as potassium tert-butoxide. 
     It will be noted by those skilled in the art that, depending on the nature of the compound to be oxidized, a mixture of diastereomers can be obtained. This can be controlled through selection of appropriate oxidation methods or, alternatively, the resulting mixture of diastereomers can be separated in a conventional manner (e.g. chromatography, fractional crystallization). 
     Compounds of Formula (I) where R 2  is H can be alkylated, acylated and carbamoylated, using standard procedures, to prepare functional derivatives of the alcohol moiety. 
     The compounds of this invention and their preparation can be understood further by the following examples, but should not constitute a limitation thereof. In these examples, unless otherwise indicated, all temperatures are in degrees centigrade and parts and percentages are by weight. 
     Nuclear magnetic resonance (nmr) spectra were obtained in CDCl 3  solution, unless otherwise noted. Abbreviations for nmr spectra are s=singlet, d=doublet, t=triplet, q=quartet, m=multiplet; peak positions are reported as parts per million downfield from tetramethylsilane. 
     EXAMPLE 1 
     PART A: 2-(4-Fluorophenyl)-2-[1-(4-fluorophenyl)-ethenyl]oxirane 
     PROCESS 1: Grignard addition to an α-Haloketone 
     To a 25° solution of Grignard reagent prepared from 6.0 g (0.030 mol) of 1-bromo-4&#39;-fluorostyrene and 0.85 g (0.035 mol) of magnesium turnings in 60 mL of THR was added a solution of 5.2 g (0.030 mol) of 2-chloro-4&#39;-fluoroacetophenone in 10 mL of THF. The solution was stirred for 2 hours at 25°. Saturated aqueous NH 4  Cl (10 mL) was added, the aqueous layer was extracted with 1:1 Et 2  O/hexane and the combined organic layers were washed with brine, dried over MgSO 4  and evaporated to give 10.2 g of an amber oil. Analysis by NMR (CDCl 3 ) indicated that the desired oxirane was the major product: δ3.1, 3.3 (two d, epoxide protons; 5.5, 5.8 (two s, vinyl protons). The material was of sufficient purity to be used in the next step. 
     PROCESS 2: Olefination of 2-(4-Fluorophenyl)-2-(4-fluorobenzoyl)oxirane 
     To a suspension of 4.3 g (0.012 mol) of methyltriphenylphosphonium bromide in 15 mL of THF cooled to -70° was added 8.4 mL (0.013 mol) of 1.55M n-butyllithium over 3 min., keeping the temperature at less than -55°. The resulting yellow suspension was allowed to warm to 0° over 10 min, and was then treated with 2.6 g (0.010 mol) of 2-(4-fluorophenyl)-2-(4-fluorobenzoyl)oxirane in 5 mL of THF. The light-brown suspension was stirred for 6 hours at 25°. Standard workup gave 3.4 g of crude product which was flash chromatographed (Et 2  O) to give 1.7 g of the desired product, which was of sufficient purity to be used in the next step. NMR (CDCl 3 ) δ3.1 (d): 3.3 (d); 5.5 (s); 5.8 (s). 
     PART B: 2,3-Bis (4-Fluorophenyl)-1-(1H-1,2,4-triazol-1-yl)-3buten-2-ol 
     A mixture of 10.2 g (0.040 mol) of crude 2-(4-fluorophenyl)-2-[1-(4-fluorophenylethenyl]oxirane and 7.0 g (0.065 mol) of potassium triazole in 60 mL of DMF was heated at 60° overnight, then cooled and poured into 100 mL of 1:1 Et 2  O/hexanes. After washing the organic layer three times with H 2  O and once with brine, a precipitate formed in the organic layer. Filtering gave 4.8 g of a brown solid which was recrystallized from 500 mL of cyclohexane to yield 2.5 g of a light-tan powder, mp 136°-137°: NMR (CDCl 3 ) δ1.7 (br s, OH); 4.7 (q, 2H); 5.3(S,1H); 5.5 (s,1H); 6.8-7.1 (m, 6H); 7.4 (m, 2H); 7.8 (s, 1H); 7.9 (s, 1H); IR (nujol) 3120 (br), 1900, 1600, 1505, 1220, 1139, 835 cm -1 . 
     The compounds shown in Table 1 were prepared or can be prepared by the method described hereinabove. 
     In the tables, Ph means phenyl and substituted aryl groups are abbreviated, e.g., 4-F-Ph is 4-fluorophenyl, 2,4-Cl 2  -Ph is 2,4-dichlorophenyl and 2-thienyl is thiophen-2-yl. 
     
         TABLE 1  ##STR31##  Ex. No. A B n R R.sup.1 R.sup.2 R.sup.3 R.sup.4 M.P.°C.   1 4-FPh 4-FPh 0 H H H H H 136-137            (HCl salt 182-184) 2 4-FPh 2,4-Cl.sub.2 Ph 0 H H H H H 139-143 3 4-FPh 4-ClPh 0 H H H H H (oil).sup.a 4 4-FPh 2,4-F.sub.2Ph 0 H H H H H   102-103.5 5 4-FPh 4-CF.sub.3Ph 0 H H H H H 6 4-FPh -n-C.sub.4 H.sub.9 0 H H H H H 72-73 7 4-FPh -n-C.sub.4 F.sub.9 0 H H H H H 8 2-FPh Ph 0 H H H H H 9 2-FPh 2-FPh 0 H H H H H 89-93 10 2-FPh 4-FPh 0 H H H H H (oil).sup.b 11 2-FPh 2,4-F.sub.2Ph 0 H H H H H 121-122 12 2-FPh 2-ClPh 0 H H H H H 13 2-FPh 4-ClPh 0 H H H H H 116-117 14 2-FPh 2,4-Cl.sub. 2Ph 0 H H H H H 115-116 15 3-FPh 4-FPh 0 H H H H H 106-109 16 3-FPh 2,4-Cl.sub.2Ph 0 H H H H H 145-147 17 3-FPh 4-ClPh 0 H H H H H 101-102 18 3-FPh 2,4-F.sub.2Ph 0 H H H H H 92-93 19 3-FPh 4-CF.sub.3Ph 0 H H H H H 20 3-FPh -n-C.sub.4 H.sub.9 0 H H H H H 21 3-FPh -n-C.sub. 4 F.sub.9 0 H H H H H 22 3-FPh Ph 0 H H H H H 23 3-FPh 2-FPh 0 H H H H H 122-124 24 3-FPh 2-ClPh 0 H H H H H 25 4-ClPh 4-FPh 0 H H H H H 110-115 26 4-ClPh 2,4-Cl.sub.2Ph 0 H H H H H 89-91          (HCl salt 184-190) 27 4-ClPh 4-ClPh 0 H H H H H 132-135 28 4-ClPh 2,4-F.sub.2Ph 0 H H H H H   124-125.5 29 4-ClPh 4-CF.sub.3Ph 0 H H H H H 30 4-ClPh -n-C.sub.4 H.sub.9 0 H H H H H 31 4-ClPh -n-C.sub.4 F.sub.9 0 H H H H H 32 2-ClPh 4-FPh 0 H H H H H (oil).sup.c 33 2-ClPh 2,4-Cl.sub.2Ph 0 H H H H H 150-152 (HCl salt 124-127) 34 2-ClPh 4-ClPh 0 H H H H H 153-154 HNO.sub.3 salt 138-141          (HCl salt 175-180) H.sub.2 SO.sub.4 salt 180-182           H.sub.3 PO.sub.4 salt 158-160 35 2-ClPh 2,4-F.sub.2Ph 0 H H H H H 128-129 H.sub.2 SO.sub.4 salt 184-187   (HCl salt 156-161) HNO.sub.3 salt 158-159           H.sub.3 PO.sub.4 salt 141-143 36 2-ClPh 4-CF.sub.3Ph 0 H H H H H 37 2-ClPh -n-C.sub.4 H.sub.9 0 H H H H H 38 2-ClPh -n-C.sub.4 F.sub.9 0 H H H H H 39 3-ClPh 4-FPh 0 H H H H H   95-96.5 40 3-ClPh 2,4-Cl.sub.2Ph 0 H H H H H 144-146 41 3-ClPh 4-ClPh 0 H H H H H 112-115 42 3-ClPh 2,4-F.sub.2Ph 0 H H H H H 115-116 43 3-ClPh 4-CF.sub.3Ph 0 H H H H H 44 3-ClPh -n-C.sub.4  H.sub.9 0 H H H H H 45 3-ClPh -n-C.sub.4 F.sub.9 0 H H H H H 46 3-ClPh Ph 0 H H H H H 47 3-ClPh 2-FPh 0 H H H H H 91-93 48 3-ClPh 2-ClPh 0 H H H H H 49 Ph 4-FPh 0 H H H H H 125-126 50 Ph 2,4-Cl.sub.2Ph 0 H H H H H 117-120 51 Ph 4-ClPh 0 H H H H H 111 52 Ph 2,4-F.sub.2Ph 0 H H H H H 119.5-122            (HCl salt 152-154) 53 Ph 4-CF.sub.3Ph 0 H H H H H 54 Ph -n-C.sub.4 H.sub.9 0 H H H H H 55 Ph -n-C.sub.4 F.sub.9 0 H H H H H 56 2-CF.sub.3Ph Ph 0 H H H H H (oil).sup.r 57 2-CF.sub.3Ph 2-FPh 0 H H H H H 127.5-130   58 2-CF.sub.3Ph 2-ClPh 0 H H H H H 152-156 59 3-CF.sub.3Ph Ph 0 H H H H H 101-103 60 3-CF.sub.3Ph 2-FPh 0 H H H H H (oil).sup.s 61 3-CF.sub.3Ph  2-ClPh 0 H H H H H 101-104 62 4-CF.sub.3Ph Ph 0 H H H H H 63 4-CF.sub.3P h 2-FPh 0 H H H H H 64 4-CF.sub.3Ph 2-ClPh 0 H H H H H 65 4-CF.sub.3Ph 4-FPh 0 H H H H H 152-154 66 4-CF.sub.3Ph 2,4-Cl.sub.2Ph 0 H H H H H (oil).sup.t 67 4-CF.sub.3Ph 4-ClPh 0 H H H H H 144-145 68 4-CF.sub.3Ph 2,4-F.sub.2Ph 0 H H H H H 69 4-CF.sub.3Ph 4-CF.sub.3Ph 0 H H H H H 70 4-CF.sub.3Ph -n-C.sub.4 H.sub.9 0 H H H H H 71 4-CF.sub.3 Ph -n-C.sub.4 H.sub.9 0 H H H H H 72 2-BrPh Ph 0 H H H H H 73 2-BrPh 2-FPh 0 H H H H H 74 2-BrPh 4-FPh 0 H H H H H 75 2-BrPh 2,4-F.sub.2Ph 0 H H H H H 76 2-BrPh 2-ClPh 0 H H H H H 77 2-BrPh 4-ClPh 0 H H H H H 78 2-BrPh 2,4-Cl.sub.2Ph 0 H H H H H 79 3-BrPh Ph 0 H H H H H 80 3-BrPh 2-FPh 0 H H H H H 81 3-BrPh 2-ClPh 0 H H H H H 82 4-BrPh Ph 0 H H H H H 83 4-BrPh 2-FPh 0 H H H H H 84 4-BrPh 2-ClPh 0 H H H H H 123-126 85 4-BrPh 4-FPh 0 H H H H H (oil).sup.d 86 4-BrPh 2,4-Cl.sub.2Ph 0 H H H H H 87 4-BrPh     P 4-Clh 0 H H H H H 145-148 88 4-BrPh 2,4-F.sub.2Ph 0 H H H H H 123-125 89 4-BrPh 4-CF.sub.3Ph 0 H H H H H 90 4-BrPh -n-C.sub.4 H.sub.9 0 H H H H H 91 4-BrPh -n-C.sub.4 F.sub.9 0 H H H H H 92 2,4-F.sub.2Ph Ph 0 H H H H H 93 2,4-F.sub.2Ph 2-FPh 0 H H H H H 106-108 94 2,4-F.sub.2Ph 4-FPh 0 H H H H H 100-103 95 2,4-F.sub.2Ph 2,4-F.sub.2Ph 0 H H H H H 116-120 96 2,4-F.sub.2Ph 2-ClPh 0 H H H H H 97 2,4-F.sub.2Ph 4-ClPh 0 H H H H H 98 2,4-F.sub.2Ph 2,4-Cl.sub.2Ph 0 H H H H H 99 2,4-Cl.sub.2Ph 4-FPh 0 H H H H H (oil).sup.e 100 2,4-Cl.sub.2Ph 2,4-Cl.sub.2Ph 0 H H H H H 75-78 101 2,4-Cl.sub.2Ph 4-ClPh 0 H H H H H 60-62 102 2,4-Cl.sub.2Ph 2,4-F.sub.2Ph 0 H H H H H 106-109 103 2,4-Cl.sub.2Ph 4-CF.sub.3Ph 0 H H H H H 104 2,4-Cl.sub.2Ph -n-C.sub.4 H.sub.9 0 H H H H H 105 2,4-Cl.sub.2Ph -n-C.sub.4 F.sub.9 0 H H H H H 106 2,4-Cl.sub.2Ph Ph 0 H H H H H 45-54 107 2,4-Cl.sub.2Ph 2-FPh 0 H H H H H 68-73 108 2,4-Cl.sub.2Ph 2-ClPh 0 H H H H H (oil).sup.u 109 3,4-Cl.sub.2Ph Ph 0 H H H H H 110 3,4-Cl.sub.2Ph 2-FPh 0 H H H H H 111 3,4-Cl.sub.2Ph 2-ClPh 0 H H H H H 112 4-.sub.-t-BuP h Ph 0 H H H H H 113 4-.sub.-t-BuPh 2-FPh 0 H H H H H 114 4-.sub.-t-BuPh 4-FPh 0 H H H H H 110-113 115 4-.sub.-t-BuPh 2,4-F.sub.2Ph 0 H H H H H 116 4-.sub.-t-BuPh 2-ClPh 0 H H H H H 117 4-.sub.-t-BuPh 4-ClPh 0 H H H H H (oil).sup.f 118 4-.sub.-t-BuPh 2,4-Cl.sub.2Ph 0 H H H H H 119 2-CH.sub.3 SPh Ph 0 H H H H H 120 2-CH.sub.3 SPh 2-FPh 0 H H H H H 121 2-CH.sub.3 SPh 4-FPh 0 H H H H H 122 2-CH.sub.3 SPh 2,4-F.sub.2Ph 0 H H H H H 123 2-CH.sub.3 SPh 2-ClPh 0 H H H H H 124 2-CH.sub.3 SPh 4-ClPh 0 H H H H H 125 2-CH.sub.3 SPh 2,4-Cl.sub.2Ph 0 H H H H H 126 2-CH.sub.3 S(O)Ph Ph 0 H H H H H 127 2-CH.sub.3 S(O)Ph 2-FPh 0 H H H H H 128 2-CH.sub.3 S(O)Ph 4-FPh 0 H H H H H 129 2-CH.sub.3 S(O)Ph 2,4-F.sub.2Ph 0 H H H H H 130 2-CH.sub.3 S(O)Ph 2-ClPh 0 H H H H H 131 2-CH.sub.3 S(O)Ph 4-ClPh 0 H H H H H 132 2-CH.sub.3 S(O)Ph 2,4-Cl.sub.2 Ph 0 H H H H H 133 2-CH.sub.3 S(O).sub.2Ph Ph 0 H H H H H 134 2-CH.sub.3  S(O).sub.2Ph 2-FPh 0 H H H H H 135 2-CH.sub.3 S(O).sub.2Ph 4-FPh 0 H H H H H 136 2-CH.sub.3  S(O).sub.2Ph 2,4-F.sub.2Ph 0 H H H H H 137 2-CH.sub.3 S(O).sub.2Ph 2-ClPh 0 H H H H H 138 2-CH.sub.3 S(O).sub.2Ph 4-ClPh 0 H H H H H 139 2-CH.sub.3 S(O).sub.2Ph 2,4-Cl.sub.2Ph 0 H H H H H 140 3-CH.sub.3 SPh Ph 0 H H H H H 141 3-CH.sub.3 SPh 2-FPh 0 H H H H H 142 3-CH.sub.3 SPh 4-FPh 0 H H H H H 143 3-CH.sub.3 SPh 2,4-F.sub.2Ph 0 H H H H H 144 3-CH.sub.3 SPh 2-ClPh 0 H H H H H 145 3-CH.sub.3 SPh 4-ClPh 0 H H H H H 146 3-CH.sub.3 SPh 2,4-Cl.sub.2Ph 0 H H H H H 147 3-CH.sub.3 S(O)Ph Ph 0 H H H H H 148 3-CH.sub.3 S(O)Ph 2-FPh 0 H H H H H 149 3-CH.sub.3 S(O)Ph 4-FPh 0 H H H H H 150 3-CH.sub.3 S(O)Ph 2,4-F.sub.2Ph 0 H H H H H 151 3-CH.sub.3 S(O)Ph 2-ClPh 0 H H H H H 152 3-CH.sub.3 S(O)Ph 4-ClPh 0 H H H H H 153 3-CH.sub.3 S(O)Ph 2,4-Cl.sub.2Ph 0 H H H H H 154 3-CH.sub.3 S(O)Ph Ph 0 H H H H H 155 3-CH.sub.3 S(O).sub.2Ph 2-FPh 0 H H H H H 156 3-CH.sub.3 S(O).sub.2Ph 4-FPh 0 H H H H H 157 3-CH.sub.3 S(O).sub.2Ph 2,4-F.sub.2Ph 0 H H H H H 158 3-CH.sub.3 S(O).sub.2Ph 2-ClPh 0 H H H H H 159 3-CH.sub.3 S(O).sub.2Ph 4-ClPh 0 H H H H H 160 3-CH.sub.3  S(O).sub.2Ph 2,4-Cl.sub.2Ph 0 H H H H H 161 4-CH.sub.3 SPh Ph 0 H H H H H 162 4-CH.sub.3 SPh 2-FPh 0 H H H H H 163 4-CH.sub.3 SPh 4-FPh 0 H H H H H 140-142 164 4-CH.sub.3 SPh 2,4-F.sub.2Ph 0 H H H H H 81-83 165 4-CH.sub.3 SPh 2-ClPh 0 H H H H H 166 4-CH.sub.3 SPh 4-ClPh 0 H H H H H 167 4-CH.sub.3 SPh 2,4-Cl.sub.2Ph 0 H H H H H 168 4-CH.sub.3 S(O)Ph Ph 0 H H H H H 169 4-CH.sub.3 S(O)Ph 2-FPh 0 H H H H H 170 4-CH.sub.3 S(O)Ph 4-FPh 0 H H H H H 81-84 171 4-CH.sub.3 S(O)Ph 2,4-F.sub.2Ph 0 H H H H H 131-134 172 4-CH.sub.3 S(O)Ph 2-ClPh 0 H H H H H 173 4-CH.sub.3 S(O)Ph 4-ClPh 0 H H H H H 174 4-CH.sub.3 S(O)Ph 2,4-Cl.sub.2Ph 0 H H H H H 175 4-CH.sub.3 S(O).sub.2Ph Ph 0 H H H H H 176 4-CH.sub.3 S(O).sub.2Ph 2-FPh 0 H H H H H 177 4-CH.sub.3 S(O).sub.2Ph 4-FPh 0 H H H H H 135 178 4-CH.sub.3 S(O).sub.2Ph 2,4-F.sub.2Ph 0 H H H H H 179 4-CH.sub.3 S(O).sub.2Ph 2-ClPh 0 H H H H H 180 4-CH.sub.3 S(O).sub.2Ph 4-ClPh 0 H H H H H 181 4-CH.sub.3 S(O).sub.2Ph 2,4-Cl.sub.2Ph 0 H H H H H 182 3--n-BuS(O)Ph 4-FPh 0 H H H H H 183 3--n-BuS(O)Ph 2,4-F.sub.2Ph 0 H H H H H 184 3--n-BuS(O)Ph 4-ClPh 0 H H H H H 185 3--n-BuS(O)Ph 2-4-Cl.sub.2Ph  0 H H H H H 186 2-CF.sub.3 OPh Ph 0 H H H H H 187 2-CF.sub.3 OPh 2-FPh 0 H H H H H 188 2-CF.sub. 3 OPh 4-FPh 0 H H H H H 189 2-CF.sub.3 OPh 2,4-F.sub.2Ph 0 H H H H H 190 2-CF.sub.3 OPh 2-ClPh 0 H H H H H 191 2-CF.sub.3 OPh 4-ClPh 0 H H H H H 192 2-CF.sub.3 OPh 2,4-Cl.sub.2Ph 0 H H H H H 193 3-CF.sub.3 OPh Ph 0 H H H H H 194 3-CF.sub.3 OPh 2-FPh 0 H H H H H 195 3-CF.sub.3 OPh 4-FPh 0 H H H H H 196 3-CF.sub.3                P  OPh 2,4-F.sub.2h 0 H H H H H 197 3-CF.sub.3 OPh 2-ClPh 0 H H H H H 198 3-CF.sub.3 OPh 4-ClPh 0 H H H H H 199 3-CF.sub.3 OPh 2,4-Cl.sub.2Ph 0 H H H H H 200 4-CF.sub.3 OPh Ph 0 H H H H H 201 4-CF.sub.3 OPh 2-FPh 0 H H H H H 202 4-CF.sub.3 OPh 4-FPh 0 H H H H H 203 4-CF.sub.3                P  OPh 2,4-F.sub.2h 0 H H H H H 204 4-CF.sub.3 OPh 2-ClPh 0 H H H H H 205 4-CF.sub.3 OPh 4-ClPh 0 H H H H H 206 4-CF.sub.3 OPh 2,4-Cl.sub.2Ph 0 H H H H H 207 4-F-1-naphthyl 2-FPh 0 H H H H H 208 1-naphthyl 4-FPh 0 H H H H H 104-106 209 1-naphthyl 2,4-F.sub.2Ph 0 H H H H H 210 1-naphthyl 2-ClPh 0 H H H H H 211 2-Cl-1-naphthyl 4-ClPh 0 H H H H H 212 1-naphthyl 2,4-Cl.sub.2Ph 0 H H H H H 213 2-naphthyl 2-FPh 0 H H H H H 214 2-naphthy l 4-FPh 0 H H H H H 215 2-naphthyl 2,4-F.sub.2Ph 0 H H H H H 216 2-naphthyl 2-Cl 0 H H H H H 217 1-Cl-2-naphthyl 4-ClPh 0 H H H H H 218 2-naphthyl 2,4-Cl.sub.2Ph 0 H H H H H 219 2-thienyl Ph 0 H H H H H 220 2-thienyl 2-FPh 0 H H H H H 221 2-thienyl 4-FPh 0 H H H H H 222 2-thienyl  2,4-F.sub.2Ph 0 H H H H H 223 2-thienyl 2-ClPh 0 H H H H H 224 2-thienyl  4-ClPh 0 H H H H H 225 2-thienyl 2,4-Cl.sub.2Ph 0 H H H H H 226 3-thienyl Ph 0 H H H H H 227 3-thienyl 2-FPh 0 H H H H H 228 3-thienyl 4-FPh 0 H H H H H 229 3-thienyl 2,4-F.sub.2Ph 0 H H H H H 230 3-thienyl 2-ClPh 0 H H H H H 231 3-thienyl 4-ClPh 0 H H H H H 232 3-thienyl 2,4-Cl.sub.2Ph 0 H H H H H 233 2-Cl-3-thienyl Ph 0 H H H H H 234 2-Cl-3-thienyl 2-FPh 0 H H H H H 235 2-Cl-3-thienyl 2-ClPh 0 H H H H H 236 5-Cl-2-thienyl Ph 0 H H H H H 237 5-Cl-2-thienyl 2-FPh 0 H H H H H 238 5-Cl-2-thienyl 2-ClPh 0 H H H H H 239 2,5-Cl.sub.2 -3-thienyl Ph 0 H H H H H 240 2,5-Cl.sub.2 -3-thienyl 2-FPh 0 H H H H H 241 2,5-Cl.sub.2 -3-thienyl 4-FPh 0 H H H H H 242 2,5-Cl.sub.2 -3-thienyl 2,4-F.sub.2Ph 0 H H H H H 243 2,5-Cl.sub.2  -3-thienyl 2-ClPh 0 H H H H H 244 2,5-Cl.sub.2 -3-thienyl 4-ClPh 0 H H H H H 245 2,5-Cl.sub.2 -3-thienyl 2,4-Cl.sub.2Ph 0 H H H H H 246 5-bromo-2-thienyl Ph 0 H H H H H 247 5-bromo-2-thienyl 2-FPh 0 H H H H H 248 5-bromo-2-thienyl 4-FPh 0 H H H H H 249 5-bromo-2-thienyl 2,4-F.sub.2P h 0 H H H H H 250 5-bromo-2-thienyl 2-ClPh 0 H H H H H 251 5-bromo-2-thie nyl 4-ClPh 0 H H H H H 252 5-bromo-2-thienyl 2,4-Cl.sub.2Ph 0 H H H H H 253 2-pyridyl Ph 0 H H H H H 254 2-pyridyl 2-FPh 0 H H H H H 255 2-pyridyl 2-ClPh 0 H H H H H 256 3-pyridyl Ph 0 H H H H H 257 3-pyridyl 2-FPh 0 H H H H H 258 3-pyridyl 2-ClPh 0 H H H H H 259 4-pyridyl Ph 0 H H H H H 260 4-pyridyl 2-F Ph 0 H H H H H 261 4-pyridyl 2-ClPh 0 H H H H H 262 5-Cl-2-pyridyl Ph 0 H H H H H 263 5-Cl-2-pyridyl 2-FPh 0 H H H H H 264 5-Cl-2-pyridyl 2-ClPh 0 H H H H H 265 2-Cl-3-pyridyl Ph 0 H H H H H 266 2-Cl-3-pyridyl 2-FPh 0 H H H H H 267 2-Cl-3-pyridyl 4-FPh 0 H H H H H 268 2-Cl-3-pyridyl 2,4-F.sub.2Ph 0 H H H H H 142-143 269 2-Cl-3-pyridyl  2-ClPh 0 H H H H H 270 2-Cl-3-pyridyl 4-ClPh 0 H H H H H 140-145 271 2-Cl-3-pyridyl 2,4-Cl.sub.2Ph 0 H H H H H 272 3-Cl-2-pyridyl Ph 0 H H H H H 273 3-Cl-2-pyridyl 2-FPh 0 H H H H H 274 3-Cl-2-pyridyl 4-FPh 0 H H H H H 275 3-Cl-2-pyridyl 2,4-F.sub.2Ph 0 H H H H H 276 3-Cl-2-pyridyl 2-ClPh 0 H H H H H 277 3-Cl-2-pyridyl 4-ClPh 0 H H H H H 278 3-Cl-2-pyrid yl 2,4-Cl.sub.2Ph 0 H H H H H 279 6-Cl-3-pyridyl Ph 0 H H H H H 280 6-Cl-3-pyridyl 2-FPh 0 H H H H H 281 6-Cl-3-pyridyl 4-FPh 0 H H H H H 282 6-Cl-3-pyridyl 2,4-F.sub.2Ph 0 H H H H H 283 6-Cl-3-pyridyl 2-ClPh 0 H H H H H 284 6-Cl-3-pyridyl 4-ClPh 0 H H H H H 285 6-Cl-3-pyridyl 2,4-Cl.sub.2Ph 0 H H H H H 286 Ph 4-FPh 0 H CH.sub.3 H H H 108-111 287 Ph 4-FPh 0 H F H H H 288 Ph 4-FPh 0 H Cl H H H 289 Ph 4-FPh 0 H Br H H H 2 90 Ph 4-FPh 0 (CH.sub.2).sub.2 H H H 291 Ph 4-FPh 0 H Ph H H H (oil).sup. g  292 Ph 4-FPh 0 CH.sub.3 CH.sub.3 H H H 293 Ph 4-FPh 0 F F H H H 294 Ph 4-FPh 0 Cl Cl H H H 295 4-FPh 4-FPh 0 H CH.sub.3 H H H 296 4-FPh 4-F Ph 0 H F H H H 297 4-FPh 4-FPh 0 H Cl H H H 298 4-FPh 4-FPh 0 H Br H H H 299 4-FPh 4-FPh 0 (CH.sub.2).sub.2 H H H 300 4-FPh 4-FPh 0 CH.sub.3 CH.sub.3 H H H 301 4-FPh 4-FPh 0 F F H H H 302 4-FPh 4-FPh 0 Cl Cl H H H 303 4-ClPh 2,4-Cl.sub.2Ph 0 H CH.sub.3 H H H 304 4-ClPh 2,4-Cl.sub.2Ph 0 H F H H H 305 4-ClPh 2,4-Cl.sub.2Ph 0 H Cl H H H 306 4-ClPh 2,4-Cl.sub.2P h 0 H Br H H H 307 4-ClPh 2,4-Cl.sub.2Ph 0 (CH.sub.2).sub.2 H H H 308 4-ClPh 2,4-Cl.sub.2Ph 0 CH.sub.3 CH.sub.3 H H H 309 4-ClPh 2,4-Cl.sub.2Ph  0 F F H H H 310 4-ClPh 2,4-Cl.sub.2Ph 0 Cl Cl H H H 311 2-ClPh 4-ClPh 0 H CH.sub.3 H H H 312 2-ClPh 4-ClPh 0 H F H H H 313 2-ClPh 4-ClPh 0 H Cl H H H 314 2-ClPh 4-ClPh 0 H Br H H H 315 2-ClPh 4-ClPh 0 (CH.sub.2).sub.2  H H H 316 2-ClPh 4-ClPh 0 CH.sub.3 CH.sub.3 H H H 317 2-ClPh 4-ClPh 0 F F H H H 318 2-ClPh 4-ClPh 0 Cl Cl H H H 319 4-FPh 4-FPh 0 H C.sub.2 H.sub.5 H H H 320 4-FPh 4-FPh 0 H .sub.-i-C.sub.3 H.sub.7 H H H 321 4-FPh 4-FPh 0 H -n-C.sub.4 H.sub.9 H H H 322 4-FPh 4-FPh 0 H Ph H H H 323 4-FPh 4-FPh 0 CH.sub.3  .sub.-t-C.sub.4 H.sub.9 H H H 324 4-FPh 4-FPh 0 CH.sub.3 Ph H H H 325 4-FPh 4-FPh 0 H I H H H 326 4-FPh 4-FPh 0 CH.sub.3 F H H H 327 4-FPh 4-FPh 0 CH.sub.3 Cl H H H 328 4-FPh 4-FPh 0 Br Br H H H 329 4-FPh 4-FPh 0 (CH.sub.2).sub.3 H H H 330 4-FPh 4-FPh 0 (CH.sub.2).sub.4 H H H 331 4-FPh 4-FPh 0 (CH.sub.2).sub.5 H H H 332 4-FPh 4-FPh 0 (CH.sub.2).sub.6 H H H 333 4-CH.sub.3Ph 4-FPh 0 H CH.sub.3 H  H H   334 4-FPh 4-FPh 1 H CH.sub.3 H H H 335 4-ClPh 4-FPh 4 H CH.sub.3 H H H 336 -n-C.sub.4  F.sub.9 4-FPh 0 H CH.sub. 3 H H H 337 (CH.sub.3).sub.2 N 4-FPh 1 H CH.sub.3 H H H 338 5-Cl-thiophen-2-yl 4-FPh 0 H CH.sub.3 H H H 339 2-Cl-thiophen-3-yl 4-FPh 0 H CH.sub.3 H H H 340 1-imidazoyl 4-FPh 0 H CH.sub.3 H H H 341 1,2,4-triazol-1-yl 4-FPh 0 H CH.sub.3 H H H 342 5-chloro-2-pyridyl 4-FPh 0 H CH.sub.3 H H H 343 4-FPh -n-C.sub.4 H.sub.9 0 H CH.sub.3 H H H 344 4-FPh .sub.-t-C.sub.4 H.sub.9 0 H CH.sub.3 H H H 345 4-FPh -n-C.sub.4 F.sub.9 0 H CH.sub.3 H H H 346 4-CH.sub.3Ph 4-FPh 0 H F H H H 347 4-FPh 4-FPh 1 H F H H H 348 4-ClPh 4-FPh 4 H F H H H 349 -n-C.sub.4 F.sub.9 4-FPh 0 H F H H H 350 (CH.sub.3).sub.2 N 4-FPh 1 H F H H H 351 5-Cl-thiophen-2-yl 4-FPh 0 H F H H H 352 2-Cl-thiophen-2-yl    P 4-Fh 0 H F H H H 353 1-imidazoyl 4-FPh 0 H F H H H 354 1,2,4-triazol-1-yl  4-FPh 0 H F H H H 355 5-Cl-2-pyridyl 4-FPh 0 H F H H H 356 4-FPh -n-C.sub.4 H.sub.9 0 H F H H H 357 4-FPh .sub.-C.sub.4 H.sub.9 0 H F H H H 358 4-FPh -n-C.sub.4 F.sub.9 0 H F H H H 359 4-FPh 4-FPh 0 H H CH.sub.3 H H (oil).sup.h 360 4-FPh 4-FPh 0 H H CH.sub.2 CHCH.sub.2 H H (oil).sup.i 361 4-FPh 4-FPh 0 H H COCH.sub.3 H H (oil).sup.j 362 4-FPh 4-FPh 0 H H CO.sub.2 CH.sub.3 H H 363 4-FPh 4-FPh 0 H H CONHCH.sub.3 H H 164-167 364 4-FPh 4-FPh 0 H H CONH-, nBu H H 365 4-FPh 4-FPh 0 H H CONHPh H H 366 4-FPh 4-F Ph 0 H H CONH-(4-FPh) H H 367 4-FPh 4-FPh 0 H H CON(CH.sub.3).sub.2 H H 368 2-ClPh 4-ClPh 0 H H CH.sub.3 H H 369 2-ClPh 4-ClPh 0 H H CH.sub.2 CHCH.sub.2 H H 370 2-ClPh 4-ClPh 0 H H COCH.sub.3 H H 371 2-ClPh 4-ClPh 0 H H CO.sub.2 CH.sub.3 H H 372 2-ClPh 4-ClPh 0 H H CONHCH.sub.3 H H 373 2-ClPh 4-ClPh 0 H H CONH-nBu H H 374 2-ClPh 4-ClPh 0 H H CONHPh H H 375 2-ClPh 4-ClPh 0 H H CONH-(4-FPh) H H 376     P 2-Clh 4-ClPh 0 H H CON(CH.sub.3).sub.2 H H 377 4-ClPh 2,4-Cl.sub.2Ph 0 H H CH.sub.3 H H 378 4-ClPh 2,4-Cl.sub.2Ph 0 H H CH.sub.2 CHCH.sub.2 H H 379 4-ClPh 2,4-Cl.sub.2Ph 0 H H COCH.sub.3 H H 380 4-ClPh 2,4-Cl.sub.2Ph 0 H H CO.sub.2 CH.sub.3 H H 381 4-ClPh 2,4-Cl.sub.2Ph 0 H H CONHCH.sub.3 H H 382 4-ClPh 2,4-Cl.sub.2Ph 0 H H CONH-nBu H H 383 4-ClPh 2,4-Cl.sub.2P h 0 H H CONHPh H H 384 4-ClPh 2,4-Cl.sub.2Ph 0 H H CONH(4-FPh) H H 385 4-ClPh 2,4-Cl.sub.2Ph 0 H H CON(CH.sub.3).sub.2 H H 386 Ph 4-FPh 0 H H CH.sub.3 H H 387 Ph 4-FPh 0 H H CH.sub.2 CHCH.sub.2 H H 388 Ph 4-FPh 0 H H COCH.sub.3 H H 389 Ph 4-FPh 0 H H CO.sub.2 CH.sub.3 H H 390 Ph 4-FPh 0 H H CONHCH.sub.3 H H 391 Ph 4-FPh 0 H H CONH-nBu H H 392 Ph 4-FPh 0 H H CONHPh H H 393 Ph 4-FPh 0 H H CONH(4-FPh) H H 394 Ph 4-FPh 0 H H CON(CH.sub.3).sub.2 H H 395 4-FPh 4-FPh 0 H H C.sub.2 H.sub.5 H H 396    P 4-Fh 4-FPh 0 H H  .sub.-i-C.sub.3 H.sub.7 H H 397 4-FPh 4-FPh 0 H H -n-C.sub.4 H.sub.9 H H 398 4-FPh 4-FPh 0 H H COC.sub.2 H.sub.5 H H 399 4-FPh 4-FPh 0 H H CO.sub.-tC.sub.4 H.sub.9 H H 400 4-FPh 4-FPh 0 H H COPh H H 401 4-FPh 4-FPh 0 H H COCH.sub.2 Ph H H 402 4-FPh 4-FPh 0 H H CONH.sub.2 H H 403 4-FPh 4-FPh 0 H H CONH.sub.-iC.sub.3 H.sub.7 H H 404 4-FPh 4-FPh 0 H H CONHCH.sub.2  Ph H H 405 4-FPh 4-FPh 0 H H CON(CH.sub.3)Ph H H 406 4-FPh 4-FPh 0 H H CONH(4-ClPh) H H 407 4-FPh 4-FPh 0 H H CONH(4-CH.sub.3Ph) H H 408 4-FPh 4-FPh 0 H H CONH(4-CH.sub.3Ph) H H 409 4-FPh 4-FPh 0 H H CONH(3-CF.sub.3P h) H H 410 4-FPh 4-FPh 0 H H CONH(4-NO.sub.2Ph) H H 411 4-FPh 4-FPh 0 H H CONH(2-CH.sub.3Ph) H H 412 4-FPh 4-FPh 0 H H CONH(2,4-F.sub.2Ph) H H 413 4-FPh 4-FPh 0 H H CONH(2,4-Cl.sub.2Ph) H H 414 4-FPh 4-FPh 0 H H CO.sub.2 C.sub.2 H.sub.5 H H 415 4-FPh 4-FPh 0 H H CO.sub.2-nC.sub.4 H.sub.9 H H 416 4-FPh 4-FPh 0 H H CO.sub.2.sub.-tC.sub.4 H.sub.9 H H 417 4-FPh 4-FPh 0 H H CO.sub.2 CH.sub.2 Ph H H 418 4-FPh 4-FPh 0 H H CO.sub.2 Ph H H 419 4-FPh 4-FPh 0 H H CF.sub.2 H H H 420 4-FPh 4-FPh 0 H H CH.sub.2 CF.sub.3 H H 421 4-FPh 4-FPh 0 H H CH.sub.2 CH.sub.2 CH.sub.2 F H H 422 4-FPh 4-FPh 0 H H CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 Cl H H 423 Ph 2,4-F.sub.2Ph 0 H H CH.sub.2CCH H H 424 Ph 4-ClPh 0 H H CH.sub.2CC H H H 425 4-FPh 2-FPh 0 H H CH.sub.2CCH H H 426 4-FPh 2-FPh 0 H H CH.sub.2CCH H H CHCl salt 184-187) 427 4-FPh 2,4-F.sub.2Ph 0 H H         CC CH.sub.2H H H 428 4-FPh 2-ClPh 0 H H CH.sub.2CCH H H 429 2-ClPh 2,4-F.sub .2Ph 0 H H CH.sub.2CCH H H 68-70 430 2-ClPh 4-ClPh 0 H H CH.sub.2CCH H H 108-111 431 4-ClPh 2-FPh 0 H H CH.sub.2C CH H H 432 4-ClPh 2,4-F.sub.2Ph 0 H H CH.sub.2CCH H H 433 4-FPh 4-FPh 1 H H H H H 434 4-FPh 4-FPh 2 H H H H H 435 4-FPh 4-FPh 3 H H H H H 436 4-FPh 4-FPh 4 H H H H H 437 2-ClPh 4-ClPh 1 H H H H H 438 2-ClPh 4-ClPh 2 H H H H H 439 2-ClPh 4-ClPh 3 H H H H H 440 2-ClPh 4-ClPh 4 H H H H H 441 4-ClPh 2,4-Cl.sub.2Ph 1 H H H H H 442 4-ClPh 2,4-Cl.sub.2Ph 2 H H H H H 443 4-ClPh 2,4-Cl.sub.2Ph 3 H H H H H 444 4-ClPh 2,4-Cl.sub.2Ph 4 H H H H H 445 Ph 4-FPh 1 H H H H H 446 Ph 4-FPh 2 H H H H H 447 OH 4-ClPh 1 H H H H H (oil).sup.k 448 OH Ph 1 H H H H H  94-100 449 OH 2,4-Cl.sub.2Ph 1 H H H H H 166-168 450 OH 4-FPh 1 H H H H H 115-116 451 OH 4-BrPh 1 H H H H H (foam).sup.1 452 OH 4-PhPh 1 H H H H H 140-143 453 (CH.sub.3).sub.2 N 2,4-Cl.sub.2Ph 1 H H H H H 104-107 454 (CH.sub.3).sub.2 N 4-FPh 1 H H H H H (oil).sup.m 455 (CH.sub.3).sub.2 N 4-BrPh 1 H H H H H (oil).sup.n 456 (CH.sub.3).sub.2 N 4-PhPh 1 H H H H H (oil).sup.o 457 1-imidazoyl 4-FPh 1 H H H H H 458 1-imidazoyl 4-FPh 2 H H H H H 459 1-imidazoyl 4-FPh 3 H H H H H 460 1-imidazoyl 4-FPh 4 H H H H H 461 1H-1,2,4-triazol-1-yl 4-FPh 1 H H H H H 462 1H-1,2,4-triazol-1-yl 4-FPh 2 H H H H H 463 1H-1,2,4-triazol-1-yl 4-FPh 3 H H H H H 464 1H-1,2,4-triazol-1-yl 4-FPh 4 H H H H H 465 1H-1,2,4-triazol-1-yl 2,4-Cl.sub.2Ph 1 H H H H H 466 1H-1,2,4-triazol-1-y l 2,4-Cl.sub.2Ph 2 H H H H H 467 1-imidazoyl 2,4-Cl.sub.2Ph 1 H H H H H 468 1-piperidyl Ph 1 H H H H H 469 1-piperidyl 2-FPh 1 H H H H H 470 1-piperidyl 4-FPh 1 H H H H H 471 1-piperidyl 2,4-F.sub.2Ph 1 H H H H H 472 1-piperidyl 2-ClPh 1 H H H H H 473 1-piperidyl 4-ClPh 1 H H H H H 474 1-piperidyl 2,4-Cl.sub.2Ph 1 H H H H H 475 2,6-(CH.sub.3).sub.2 -1-morpholinyl Ph 1 H H H H H 476 2,6-(CH.sub.3).sub.2 -1-morpholinyl    P 2-Fh 1 H H H H H 477 2,6-(CH.sub.3).sub.2 -1-morpholinyl 4-FPh 1 H H H H H 97-99 478 2,6-(CH.sub.3).sub.2 -1-morpholinyl 2,4-F.sub.2Ph 1 H H H H H 479 2,6-(CH.sub.3).sub.2 -1-morpholinyl 2-ClPh 1 H H H H H 480 2,6-(CH.sub.3).sub.2 -1-morpholinyl 4-ClPh 1 H H H H H 481 2,6-(CH.sub. 3).sub.2 -1-morpholinyl 2,4-Cl.sub.2Ph 1 H H H H H 482 4-CH.sub.3 -1-piperazinyl Ph 1 H H H H H 483 4-CH.sub.3 -1-piperazinyl 2-FPh 1 H H H H H 484 4-CH.sub.3 -1-piperazinyl 4-FPh 1 H H H H H 485 4-CH.sub.3 -1-piperazinyl 2,4-F.sub.2Ph 1 H H H H H 486 4-CH.sub.3 -1-piperazinyl 2-ClPh 1 H H H H H 487 4-CH.sub.3 -1-piperazinyl 4-ClPh 1 H H H H H 488 4-CH.sub.3  -1-piperazinyl 2,4-Cl.sub.2Ph 1 H H H H H 489 4--n-Bu-1-piperazinyl Ph 1 H H H H H 490 4--n-Bu-1-piperazinyl 2-FPh 1 H H H H H 491 4--n-Bu-1-pip erazinyl 4-FPh 1 H H H H H 492 4--n-Bu-1-piperazinyl 2,4-F.sub.2Ph 1 H H H H H 493 4--n-Bu-1-piperazinyl 2-ClPh 1 H H H H H 494 4--n-Bu-1-piperazi nyl 4-ClPh 1 H H H H H 495 4--n-Bu-1-piperazinyl 2,4-Cl.sub.2Ph 1 H H H H H 496 4-acetyl-1-piperazinyl Ph 1 H H H H H 497 4-acetyl-1-piperazinyl 2-FPh 1 H H H H H 498 4-acetyl-1-piperazinyl 4-FPh 1 H H H H H 499 4-acetyl-1-piperazinyl 2,4-F.sub.2Ph 1 H H H H H 500 4-acetyl-1-piperazin yl 2-ClPh 1 H H H H H 501 4-acetyl-1-piperazinyl 4-ClPh 1 H H H H H 502 4-acetyl-1-piperazinyl 2,4-Cl.sub.2Ph 1 H H H H H 503 2-(2-pyridyl)-Ph 4-FPh 0 H H H H H 504 2-(3-pyridyl)-Ph 4-FPh 0 H H H H H 505 2-(4-pyridyl )-Ph 4-FPh 0 H H H H H 506 3-(2-pyridyl)-Ph 4-FPh 0 H H H H H 507 3-(3-pyridyl)-Ph 4-FPh 0 H H H H H 508 3-(4-pyridyl)-Ph 4-FPh 0 H H H H H 509 4-(2-pyridyl)-Ph 4-FPh 0 H H H H H 510 4-(3-pyridyl)-Ph 4-FPh 0 H H H H H 511 4-(4-pyridyl)-Ph 4-FPh 0 H H H H H 512 2-(1H-1,2,4-triazol-1- yl)-Ph 4-FPh 0 H H H H H 513 3-(1H-1,2,4-triazol-1-yl)-Ph 4-FPh 0 H H H H H 514 4-(1H-1,2,4-triazol-1-yl)-Ph 4-FPh 0 H H H H H 515 2-(imidazol-1- yl)-Ph 4-FPh 0 H H H H H 516 3-(imidazol-1-yl)-Ph 4-FPh 0 H H H H H 517 4-(imidazol-1-yl)-Ph 4-FPh 0 H H H H H 518 2-(4-methylpiperazin-1-yl)-Ph 4-FPh 0 H H H H H 519 3-(4-methylpiperazin-1-yl)-Ph 4-FPh 0 H H H H H 520 4-(4-methylpiperazin-1-yl)-Ph 4-FPh 0 H H H H H 521 2-(4-acetylpipera zin-1-yl)-Ph 4-FPh 0 H H H H H 522 3-(4-acetylpiperazin-1-yl)-Ph 4-FPh 0 H H H H H 523 4-(4-acetylpiperazin-1-yl)-Ph 4-FPh 0 H H H H H 524 2-(2-pyridyl)-Ph 2,4-F.sub.2Ph 0 H H H H H 525 2-(3-pyridyl)-Ph 2,4-F.sub .2Ph 0 H H H H H 526 2-(4-pyridyl)-Ph 2,4-F.sub.2Ph 0 H H H H H 527 3-(2-pyridyl)-Ph 2,4-F.sub.2Ph 0 H H H H H 528 3-(3-pyridyl)-Ph 2,4-F.sub .2Ph 0 H H H H H (Foam).sup.am 529 3-(4-pyridyl)-Ph 2,4-F.sub.2Ph 0 H H H H H 530 4-(2-pyridyl)-Ph 2,4-F.sub.2Ph 0 H H H H H 531 4-(3-pyridyl)-Ph  2,4-F.sub.2Ph 0 H H H H H (Foam).sup.an 532 4-(4-pyridyl)-Ph 2,4-F.sub.2P h 0 H H H H H 533 2-(1H-1,2,4-triazol-1-yl)-Ph 2,4-F.sub.2Ph 0 H H H H H 534 3-(1H-1,2,4-triazol-1-yl)-Ph 2,4-F.sub.2Ph 0 H H H H H 535 4-(1H-1,2, 4-triazol-1-yl)-Ph 2,4-F.sub.2Ph 0 H H H H H 536 2-(imidazol-1-yl)-Ph 2,4-F.sub.2Ph 0 H H H H H 537 3-(imidazol-1-yl)-Ph 2,4-F.sub.2Ph 0 H H H H H 538 4-(imidazol-1-yl)-Ph 2,4-F.sub.2Ph 0 H H H H H 539 2-(4-methylpip erazin-2-yl)-Ph 2,4-F.sub.2Ph 0 H H H H H 540 3-(4-methylpiperazin-2-yl)- Ph 2,4-F.sub.2Ph 0 H H H H H 541 4-(4-methylpiperazin-2-yl)-Ph 2,4-F.sub. 2Ph 0 H H H H H 542 2-(4-acetylpiperazin-1-yl)-Ph 2,4-F.sub.2Ph 0 H H H H H 543 3-(4-acetylpiperazin-1-yl)-Ph 2,4-F.sub.2Ph 0 H H H H H 544 4-(4-acetylpiperazin-1-yl)-Ph 2,4-F.sub.2Ph 0 H H H H H 545 2-Cl-3-(3-pyr idyl)-Ph 2,4-F.sub.2Ph 0 H H H H H 546 2-(2-pyridyl)-Ph 4-ClPh 0 H H H H H 547 2-(3-pyridyl)-Ph 4-ClPh 0 H H H H H 548 2-(4-pyridyl)-Ph 4-ClPh 0 H H H H H 549 3-(2-pyridyl)-Ph 4-ClPh 0 H H H H H 550 3-(3-pyridyl)-Ph 4-ClPh 0 H H H H H 551 3-(4-pyridyl)-Ph 4-ClPh 0 H H H H H 552 4-(2-pyrid yl)-Ph 4-ClPh 0 H H H H H 553 4-(3-pyridyl)-Ph 4-ClPh 0 H H H H H 554 4-(4-pyridyl)-Ph 4-ClPh 0 H H H H H 555 2-(1H-1,2,4-triazol-1-yl)-Ph     P 4-Clh 0 H H H H H 556 3-(1H-1,2,4-triazol-1-yl)-Ph 4-ClPh 0 H H H H H 557 4-(1H-1,2,4-triazol-1-yl)-Ph 4-ClPh 0 H H H H H 558 2-(imidazol-1-yl) -Ph 4-ClPh 0 H H H H H 559 3-(imidazol-1-yl)-Ph 4-ClPh 0 H H H H H 560 4-(imidazol-1-yl)-Ph 4-ClPh 0 H H H H H 561 2-(4-methylpiperazin-1-yl)-Ph  4-ClPh 0 H H H H H 562 3-(4-methylpiperazin-1-yl)-Ph 4-ClPh 0 H H H H H 563 4-(4-methylpiperazin-1-yl)-Ph 4-ClPh 0 H H H H H 564 2-(4-acetylpiper azin-1-yl)-Ph 4-ClPh 0 H H H H H 565 2-(4-acetylpiperazin-1-yl)-Ph 4-ClPh 0 H H H H H 566 4-(4-acetylpiperazin-1-yl)-Ph 4-ClPh 0 H H H H H 567 2-Cl-3-(3-pyridyl)-Ph 4-ClPh 0 H H H H H 568 2-(2-pyridyl)-Ph 2,4-Cl.sub.2Ph 0 H H H H H 569 2-(3-pyridyl)-Ph 2,4-Cl.sub.2Ph 0 H H H H H 570 2-(4-pyridyl)-Ph 2,4-Cl.sub.2Ph 0 H H H H H 571 3-(2-pyridyl)-Ph 2,4-Cl.sub.2Ph 0 H H H H H 572 3-(3-pyridyl)-Ph 2,4-Cl.sub.2Ph 0 H H H H H 573 3-(4-pyridyl)-Ph 2,4-Cl.sub.2Ph 0 H H H H H 574 4-(2-pyridyl)-Ph 2,4-Cl.sub.2Ph 0 H H H H H 575 4-(3-pyridyl)-Ph 2,4-Cl.sub.2Ph 0 H H H H H 576 4-(4-pyridyl)-Ph 2,4-Cl.sub.2Ph 0 H H H H H 577 2-(1H-1,2,4-triazol -1-yl)-Ph 2,4-Cl.sub.2Ph 0 H H H H H 578 3-(1H-1,2,4-triazol-1-yl)-Ph 2,4-Cl.sub.2Ph 0 H H H H H 579 4-(1H-1,2,4-triazol-1-yl)-Ph 2,4-Cl.sub.2P h 0 H H H H H 580 2-(imidazol-1-yl)-Ph 2,4-Cl.sub.2Ph 0 H H H H H 581 3-(imidazol-1-yl)-Ph 2,4-Cl.sub.2Ph 0 H H H H H 582 4-(imidazol-1-yl)-Ph 2,4-Cl.sub.2Ph 0 H H H H H 583 2-(4-methylpiperazin-1-yl)-Ph 2,4-Cl.sub.2P h 0 H H H H H 584 3-(4-methylpiperazin-1-yl)-Ph 2,4-Cl.sub.2Ph 0 H H H H H 585 4-(4-methylpiperazin-1-yl)-Ph 2,4-Cl.sub.2Ph 0 H H H H H 586 2-(4-acetylpiperazin-1-yl)-Ph 2,4-Cl.sub.2Ph 0 H H H H H 587 3-(4-acetylp iperazin-1-yl)-Ph 2,4-Cl.sub.2Ph 0 H H H H H 588 4-(4-acetylpiperazin-1-y l)-Ph 2,4-Cl.sub.2Ph 0 H H H H H 589 2-Cl-3-(3-pyridyl)-Ph 2,4-Cl.sub.2Ph  0 H H H H H 590 3-(morpholin-1-yl)-Ph 2,4-F.sub.2Ph 0 H H H H H 591 3-(2,6-dimethyl-morpholin-1-yl)-Ph 2,4-F.sub.2Ph 0 H H H H H 592 4-( -n-butyl-piperazin-1-yl)-Ph 2,4-F.sub.2Ph 0 H H H H H 593 4-(piperidi n-1-yl)-Ph 2,4-F.sub.2Ph 0 H H H H H 594 Ph 2-FPh 0 H H H H H (oil).sup.p  (HCl salt 190-195) 595 Ph 3-FPh 0 H H H H H 596 Ph 2-ClPh 0 H H H H H 78-80 597 Ph 3-ClPh 0 H H H H H 598 Ph 4-Br-Ph 0 H H H H H 92-95 599 Ph 4-IPh 0 H H H H H 600 Ph 3,4-F.sub.2Ph 0 H H H H H 601 Ph 3,4-Cl.sub.2Ph 0 H H H H H 602 Ph 2,6-Cl.sub.2Ph 0 H H H H H 603 Ph 3,5-Cl.sub.2Ph 0 H H H H H 142-144 604 Ph 2-Cl(4-F)-Ph 0 H H H H H 605 Ph 3-Cl(4-F)-Ph 0 H H H H H 199-124 (dec.) 606 Ph 2,4,6-Cl.sub.3Ph 0 H H H H H 607 Ph 2-F(4-Cl)-Ph 0 H H H H H 608 Ph Ph 0 H H H H H 130-133 609 Ph 4-CH.sub.3P h 0 H H H H H 610 Ph 3-CH.sub.3Ph 0 H H H H H 611 Ph 2-CH.sub.3Ph 0 H H H H H 160.5-163   612 Ph 2-CF.sub.3Ph 0 H H H H H 613 Ph 3-CF.sub.3Ph 0 H H H H H 614 Ph 2-Cl-3-thienyl 0 H H H H H 615 Ph 2-F(4-CF.sub.3)-Ph 0 H H H H H 616 Ph 4-CH.sub.3 OPh 0 H H H H H 617 Ph 5-Cl-2-pyridyl 0 H H H H H 618 Ph 5-Cl-2-thienyl 0 H H H H H 88-90 619 Ph .sub.-s-C.sub.4 H.sub.9 0 H H H H H 620 2-ClPh 2-FPh 0 H H H H H 118-119 621 2-ClPh 3-FPh 0 H H H H H 622 2-ClPh 2-ClPh 0 H H H H H 149-150 623 2-ClPh 3-ClPh 0 H H H H H 624 2-ClPh 4-BrPh 0 H H H H H 151-152 625 2-ClPh 4-IPh 0 H H H H H 626 2-ClPh 3,4-F.sub.2 Ph 0 H H H H H 627 2-ClPh 3,4-Cl.sub.2Ph 0 H H H H H   122-123.5 628 2-ClPh 2,6-Cl.sub.2Ph 0 H H H H H 629 2-ClPh 2-Cl(4-F)-Ph 0 H H H H H 630 2-ClPh 2,4,6-Cl.sub.3Ph 0 H H H H H 631 2-ClPh 2-F(4-Cl)-Ph 0 H H H H H 632 2-ClPh Ph 0 H H H H H 633 2-ClPh 4-CH.sub.3Ph 0 H H H H H 634 2-ClPh 3-CH.sub.3Ph 0 H H H H H 635 2-ClPh 2-CH.sub.3Ph 0 H H H H H 636 2-ClPh 2-CF.sub.3Ph 0 H H H H H 637 2-ClPh 3-CF.sub.3Ph 0 H H H H H 638 2-ClPh 2-F(4-CF.sub.3)-Ph 0 H H H H H 639 2-ClPh 4-CH.sub.3 OPh 0 H H H H H 640 2-ClPh 5-Cl-2-pyridyl 0 H H H H H 641 2-ClPh 5-Cl-2-thienyl 0 H H H H H (oil).sup.v 642 2-ClPh 2-Cl-3-thienyl 0 H H H H H 643 2-ClPh .sub.-s-C.sub.4 H.sub.9 0 H H H H H 644 4-FPh 2-FPh 0 H H H H H 96-97 645 4-FPh 3-FPh 0 H H H H H 646 4-FPh 2-ClPh 0 H H H H H 116-119 647 4-FPh 3-ClPh 0 H H H H H 648 4-FPh 4-BrPh 0 H H H H H 114-116 649 4-FPh 4-IPh 0 H H H H H 650 4-FPh 3,4-F.sub.2Ph 0 H H H H H 651 4-FPh 3,4-Cl.sub.2Ph 0 H H H H H 98-99 652 4-FPh 2,6-Cl.sub.2Ph 0 H H H H H 653 4-FPh 2-Cl(4-F)-Ph 0 H H H H H 128-130 654 4-FPh 2,4,6-Cl.sub.3Ph 0 H H H H H 655 4-FPh 2-F(4-Cl)-Ph 0 H H H H H 656 4-FPh Ph 0 H H H H H 124-125 657 4-FPh 4-PhPh 0 H H H H H 116-119 658 4-FPh 4-CH.sub.3Ph 0 H H H H H 145-147 659 4-FPh 2-CH.sub.3Ph  0 H H H H H 145-149 660 4-FPh 2-CF.sub.3Ph 0 H H H H H 661 4-FPh 3-CF.sub.3Ph 0 H H H H H 121-122 662 4-FPh 2-F(4-CF.sub.3)-Ph 0 H H H H H 663 4-FPh 4-CH.sub.3 OPh 0 H H H H H 112-114 664 4-FPh 5-Cl-2-pyridyl 0 H H H H H 665 4-FPh 5-Cl-2-thienyl 0 H H H H H 114-115 666 4-FPh 2-Cl-3-thienyl 0 H H H H H 667 4-FPh .sub.-i-C.sub.3 H.sub.7 0 H H H H H 74-75 668 4-FPh C.sub.2 H.sub.5 0 H H H H H (oil).sup.q 669 4-ClPh 2-FPh 0 H H H H H 130-131 670 4-ClPh 3-FPh 0 H H H H H 671 4-ClPh 2-ClPh 0 H H H H H 137-139 672 4-ClPh 3-ClPh 0 H H H H H 673 4-ClPh 4-BrPh 0 H H H H H 121-123 674 4-ClPh 4-I Ph 0 H H H H H 675 4-ClPh 3,4-Cl.sub.2Ph 0 H H H H H 107-198 676 4-ClPh 2,6-Cl.sub.2Ph 0 H H H H H 677 4-ClPh 2-Cl(4-F)- Ph 0 H H H H H 678 4-ClPh 2,4,6-Cl.sub.3Ph 0 H H H H H 679 4-ClPh 2-F(4-Cl)-Ph 0 H H H H H 680 4-ClPh Ph 0 H H H H H 681 4-ClPh 4-CH.sub.3P h 0 H H H H H 682 4-ClPh 3-CH.sub.3Ph 0 H H H H H 683 4-ClPh 2-CH.sub.3Ph  0 H H H H H 684 4-ClPh 2-CF.sub.3Ph 0 H H H H H 685 4-ClPh 3-CF.sub.3Ph 0 H H H H H 103-104 686 4-ClPh 2-F(4-CF.sub.3)-Ph 0 H H H H H 687 4-ClPh 4-CH.sub.3 OPh 0 H H H H H 688 4-ClPh 5-Cl-2-pyridyl 0 H H H H H 689     P 4-Clh 5-Cl-2-thienyl 0 H H H H H (oil).sup.w 690 4-ClPh 2-Cl-3-thienyl 0 H H H H H 691 4-ClPh .sub.-s-C.sub.4 H.sub.9 0 H H H H H  692 4-FPh  ##STR32##  0 H H H H H  693 4-FPh .sub.-t-butyl 0 H H H H H 694 4-FPh -n-hexyl 0 H H H H H 695 4-FPh -n-heptyl 0 H H H H H 696 4-FPh 2,4-(CH.sub.3).sub.2Ph 0 H H H H H 148-149 697 4-FPh C.sub.6 F.sub.13 0 H H H H H 698 4-FPh C.sub.8 F.sub.17 0 H H H H H 699 4-FPh 4-pyridyl 0 H H H H H 175-178 700 4-FPh 2-pyridyl 0 H H H H H 701 4-FPh 2-thienyl 0 H H H H H 702 4-FPh    n 4---BuPh 0 H H H H H 703 4-FPh 4--n-BuOPh 0 H H H H H 704 4-FPh 5-CF.sub. 3 -pyrid-2-yl 0 H H H H H 705 4-FPh 5-MeSO.sub.2 -2-thienyl 0 H H H H H 706 4-C.sub.2 H.sub.5Ph 4-FPh 0 H H H H H 707 4-(-n-BuO)-Ph 4-FPh 0 H H H H H 708 2-CH.sub.3 SO.sub.2 -imidazol-1-yl 4-FPh 0 H H H H H 709 5-CH.sub.3 -1,2,4-triazol-1-yl 4-FPh 0 H H H H H 710 C.sub.6 F.sub.13    P 4-Fh 0 H H H H H 711 C.sub.8  F.sub.17 4-FPh 0 H H H H H 712 2-Cl-3-(3-pyridyl)-Ph 4-FPh 0 H H H H H 713 2-CF.sub.3 -imidazol-1-yl 4-FPh 0 H H H H H 714 4-(.sub.-i-PrO)-Ph 4-FPh 0 H H H H H 715 4-IPh 4-FPh 0 H H H H H 716 3,4-F.sub.2Ph 4-FPh 0 H H H H H 717 3,4-Cl.sub.2Ph 4-FPh 0 H H H H H 718 2,6-Cl.sub.2Ph 4-FPh 0 H H H H H 719 2-Cl(4-F)-Ph 4-FPh 0 H H H H H 720 2,4,6-Cl.sub.3Ph 4-FPh 0 H H H H H 721 4-CH.sub.3Ph 4-FPh 0 H H H H H 119-120 722 3-CH.sub.3Ph 4-FPh 0 H H H H H 723 2-CH.sub.3Ph 4-FPh 0 H H H H H 181-184 724 2-CF.sub.3Ph 4-FPh 0 H H H H H 110-112 725 3-CF.sub.3Ph 4-FPh 0 H H H H H 106-108 726 4-CH.sub.3 OPh 4-FPh 0 H H H H H 109-111 727 2,3-Cl.sub.2Ph 4-FPh 0 H H H H H 728 3,5-Cl.sub.2Ph 4-FPh 0 H H H H H 729 2,5-Cl.sub.2Ph 4-FPh 0 H H H H H 730 3-BrPh 4-FPh 0 H H H H H 91-93 731 4-EtOPh 4-FPh 0 H H H H H 732 2,4-(CH.sub.3).sub.2Ph 4-FPh 0 H H H H H 733 2,4,6-(CH.sub.3).sub.3Ph 4-FPh 0 H H H H H 734 4-PhPh 4-FPh 0 H H H H H 735 5-Cl-2-thienyl 4-FPh 0 H H H H H 736 2-Cl-3-thienyl 4-FPh 0 H H H H H 737 1-imidazoyl 4-FPh 0 H H H H H 738 1H-1,2,4-triazoly  4-FPh 0 H H H H H 739 2-pyridyl 4-FPh 0 H H H H H 740 5-Cl-pyrid-2-yl 4-FPh 0 H H H H H 741 3-pyridyl 4-FPh 0 H H H H H 742 4-pyridyl 4-FPh 0 H H H H H 743 -n-C.sub.4                                                 P  F.sub.9 4-FPh 0 H H H H H 744 4-IPh 2,4-Cl.sub.2h 0 H H H H H 745 3,4-F.sub.2Ph 2,4-Cl.sub.2Ph 0 H H H H H 746 3,4-Cl.sub.2Ph 2,4-Cl.sub.2P h 0 H H H H H 747 2,6-Cl.sub.2Ph 2,4-Cl.sub.2Ph 0 H H H H H 748 2-Cl(4-F) -Ph 2,4-Cl.sub.2Ph 0 H H H H H 749 2,4,6-Cl.sub.3Ph 2,4-Cl.sub.2Ph 0 H H H H H 750 4-CH.sub.3Ph 2,4-Cl.sub.2Ph 0 H H H H H 751 3-CH.sub.3Ph 2,4-Cl.sub.2Ph 0 H H H H H 752 2-CH.sub.3Ph 2,4-Cl.sub.2Ph 0 H H H H H 753 2-CF.sub.3 Ph 2,4-Cl.sub.2Ph 0 H H H H H 133-137 754 3-CF.sub.3Ph 2,4-Cl.sub.2Ph 0 H H H H H 77-84 755 4-CH.sub.3 OPh 2,4-Cl.sub.2Ph 0 H H H H H 756 2,3-Cl.sub.2Ph 2,4-Cl.sub.2Ph 0 H H H H H 757 3,5-Cl.sub.2Ph 2,4-Cl.sub.2Ph 0 H H H H H 758 2,5-Cl.sub.2Ph 2,4-Cl.sub.2Ph 0 H H H H H 759 3-BrPh 2,4-Cl.sub.2Ph 0 H H H H H 171-173 760 4-EtOPh 2,4-Cl.sub.2Ph 0 H H H H H 761 2,4-(CH.sub.3).sub.2Ph 2,4-Cl.sub.2Ph 0 H H H H H 762 2,4,6-(CH.sub.3).sub.3Ph 2,4-Cl.sub.2Ph 0 H H H H H 763 4-PhPh 2,4-Cl.sub .2Ph 0 H H H H H 764 5-Cl-2-thienyl 2,4-Cl.sub.2Ph 0 H H H H H 765 2-Cl-3-thienyl 2,4-Cl.sub.2Ph 0 H H H H H 766 1-imidazoyl 2,4-Cl.sub.2Ph 0 H H H H H 767 1H-1,2,4-triazoyl-1-yl 2,4-Cl.sub.2Ph 0 H H H H H 768 2-pyridyl 2,4-Cl.sub.2Ph 0 H H H H H 769 5-Cl-pyrid-2-yl 2,4-Cl.sub.2Ph 0 H H H H H 770 3-pyridyl 2,4-Cl.sub.2Ph 0 H H H H H 771 4-pyridyl 2,4-Cl.sub.2Ph 0 H H H H H 772 -n-C.sub.4 F.sub.9 2,4-Cl.sub.2Ph 0 H H H H H 773 4-IPh 4-ClPh 0 H H H H H 774 3,4-F.sub.2Ph 4-ClPh 0 H H H H H 775 3,4-Cl.sub.2Ph 4-ClPh 0 H H H H H 776 2,6-Cl.sub.2Ph 4-ClPh 0 H H H H H 777 2-Cl(4-F)-Ph 4-ClPh 0 H H H H H 778 2,4,6-Cl.sub.3Ph 4-ClPh 0 H H H H H 779 4-CH.sub.3Ph 4-ClPh 0 H H H H H 780 3-CH.sub.3Ph 4-ClPh 0 H H H H H 781 2-CH.sub.3Ph 4-ClPh 0 H H H H H 782 2-CF.sub.3Ph 4-ClPh 0 H H H H H 43-49 783 3-CF.sub.3Ph 4-ClPh 0 H H H H H 109-112 784 4-CH.sub.3 OPh 4-ClPh 0 H H H H H 111-113 785 2,3-Cl.sub.2Ph 4-ClPh 0 H H H H H 786 3,5-Cl.sub.2Ph 4-ClPh 0 H H H H H 787 2,5-Cl.sub.2Ph 4-ClPh 0 H H H H H 788 3-BrPh 4-ClPh 0 H H H H H 119-121 789 4-EtOPh 4-ClPh 0 H H H H H 790 2,4-(CH.sub.3).sub.2Ph 4-ClPh 0 H H H H H 791 2,4,6-(CH.sub.3).sub.3Ph 4-ClPh 0 H H H H H 792 4-PhPh 4-ClPh 0 H H H H H 793 5-Cl-2-thienyl 4-ClPh 0 H H H H H 794 2-Cl-3-thienyl 4-ClPh 0 H H H H H 795 1-imidazoyl 4-ClPh 0 H H H H H 796 1H-1,2,4-triazoly-1-yl 4-ClPh 0 H H H H H 797 2-pyridyl 4-ClPh 0 H H H H H 798 5-Cl-pyrid-2-yl 4-ClPh 0 H H H H H 799 3-pyridyl 4-ClPh 0 H H H H H 800 4-pyridyl 4-ClPh 0 H H H H H (oil).sup.a f 801 -n-C.sub.4 F.sub.9 4-ClPh 0 H H H H H 802 4-IPh 2,4-F.sub.2Ph 0 H H H H H 803 3,4-F.sub.2Ph 2,4-F.sub.2Ph 0 H H H H H 804 3,4-Cl.sub.2Ph 2,4-F.sub.2Ph 0 H H H H H 805 2,6-Cl.sub.2Ph 2,4-F.sub.2Ph 0 H H H H H 806 2-Cl(4-F)-Ph 2,4-F.sub.2Ph 0 H H H H H 807 2,4,6-Cl.sub.3Ph 2,4-F.sub .2Ph 0 H H H H H 808 4-CH.sub.3Ph 2,4-F.sub.2Ph 0 H H H H H 129-130.5 809 3-CH.sub.3Ph 2,4-F.sub.2Ph 0 H H H H H 810 2-CH.sub.3Ph 2,4-F.sub.2Ph  0 H H H H H 811 2-CF.sub.3Ph 2,4-F.sub.2Ph 0 H H H H H 113-116 812 3-CF.sub.3Ph 2,4-F.sub.2Ph 0 H H H H H 123-124 813 4-CH.sub.3 OPh 2,4-F.sub.2Ph 0 H H H H H 88-89 814 2,3-Cl.sub.2Ph 2,4-F.sub.2Ph 0 H H H H H 815 3,5-Cl.sub.2Ph 2,4-F.sub.2Ph 0 H H H H H 173-175 816 2,5-Cl.sub.2P h 2,4-F.sub.2Ph 0 H H H H H 817 3-BrPh 2,4-F.sub.2Ph 0 H H H H H 103-107 818 4-EtOPh 2,4-F.sub.2Ph 0 H H H H H 819 2,4-(CH.sub.3).sub.2Ph 2,4-F.sub.2Ph 0 H H H H H 820 2,4,6-(CH.sub.3).sub.3Ph 2,4-F.sub.2Ph 0 H H H H H 821 4-PhPh 2,4-F.sub.2Ph 0 H H H H H 822 5-Cl-2-thienyl 2,4-F.sub .2Ph 0 H H H H H 823 2-Cl-3-thienyl 2,4-F.sub.2Ph 0 H H H H H 824 1-imidazoyl 2,4-F.sub.2Ph 0 H H H H H 825 1H-1,2,4-triazoyl-1-yl 2,4-F.sub.2Ph 0 H H H H H 826 2-pyridyl 2,4-F.sub.2Ph 0 H H H H H 827 5-Cl-pyrid-2-yl 2,4-F.sub.2Ph 0 H H H H H 828 3-pyridyl 2,4-F.sub.2Ph 0 H H H H H 829 4-pyridyl 2,4-F.sub.2Ph 0 H H H H H 830 -n-C.sub.4 F.sub.9 2,4-F.sub.2Ph 0 H H H H H 831 2-FPh 4-BrPh 0 H H H H H 832 3-FPh 4-BrPh 0 H H H H H 833 3-ClPh 4-BrPh 0 H H H H H 834 4-BrPh 4-BrPh 0 H H H H H 835 2,4-F.sub.2Ph 4-BrPh 0 H H H H H 836 2,4-Cl.sub.2Ph 4-BrPh 0 H H H H H 837 2-CF.sub.3Ph 4-BrPh 0 H H H H H 838 3-CF.sub.3Ph 4-BrPh 0 H H H H H 839 4-CF.sub.3Ph 4-BrPh 0 H H H H H 840 2-FPh 4-IPh 0 H H H H H 841    P 3-Fh 4-IPh 0 H H H H H 842 3-ClPh 4-IPh 0 H H H H H 843 4-BrPh 4-IPh 0 H H H H H 844 2,4-F.sub.2Ph 4-IPh 0 H H H H H 845 2,4-Cl.sub.2Ph 4-IPh 0 H H H H H 846 2-CF.sub.3Ph 4-IPh 0 H H H H H 847 3-CF.sub.3Ph 4-IPh 0 H H H H H 848 4-CF.sub.3Ph 4-IPh 0 H H H H H 849 2-FPh 2-CH.sub.3Ph 0 H H H H H 850 3-FPh 2-CH.sub.3Ph 0 H H H H H 851 3-ClPh 2-CH.sub.3Ph 0 H H H H H 852 4-BrPh 2-CH.sub.3Ph 0 H H H H H 853 2,4-F.sub.2Ph 2-CH.sub.3Ph 0 H H H H H 854 2,4-Cl.sub.2Ph 2-CH.sub.3Ph 0 H H H H H 855 2-CF.sub.3Ph 2-CH.sub.3Ph 0 H H H H H 856 3-CF.sub.3Ph 2-CH.sub.3Ph 0 H H H H H 857 4-CF.sub.3Ph 2-CH.sub.3Ph 0 H H H H H 858 4-(4-FPh)-Ph 4-FPh 0 H H H H H 859 4-(2-ClPh)-Ph 4-ClPh 0 H H H H H 860 3-(3-CF.sub.3Ph)-Ph 2,4-F.sub.2P h 0 H H H H H 861 3-(2,4-F.sub.2Ph)-Ph 2,4-Cl.sub.2Ph 0 H H H H H 862 2,4-F.sub.2Ph 4-CH.sub.3Ph 0 H H H H H 863 4-CH.sub.3Ph 4-CH.sub.3Ph 0 H H H H H 178-181.5 864 2-CF.sub.3Ph 4-CH.sub.3Ph 0 H H H H H 865 3-CF.sub. 3Ph 4-CH.sub.3Ph 0 H H H H H 866 4-CF.sub.3Ph 4-CH.sub.3Ph 0 H H H H H 867 2-FPh 4-CH.sub.3 OPh 0 H H H H H 868 3-FPh 4-CH.sub.3 OPh 0 H H H H H 869 4-ClPh 4-CH.sub.3 OPh 0 H H H H H 870 4-BrPh 4-CH.sub.3 OPh 0 H H H H H 871 2,4-F.sub.2Ph 4-CH.sub.3 OPh 0 H H H H H 872 2,4-Cl.sub.2Ph 4-CH.sub.3 OPh 0 H H H H H 873 2-CF.sub.3Ph 4-CH.sub.3 OPh 0 H H H H H 874 3-CF.sub.3Ph 4-CH.sub.3 OPh 0 H H H H H 875 4-CF.sub.3Ph 4-CH.sub.3  P Oh 0 H H H H H 876 Ph 2-CH.sub.3 OPh 0 H H H H H 877 2-FPh 2-CH.sub.3 OPh 0 H H H H H 878 3-FPh 2-CH.sub.3  OPh 0 H H H H H 879 4-FPh 2-CH.sub.3 OPh 0 H H H H H 56-70 (138- 139.5 .H.sub.2 C.sub.2 O.sub.4) 880 2,4-F.sub.2Ph 2-CH.sub.3 OPh 0 H H H H H 881 2-ClPh 2-CH.sub.3 OPh 0 H H H H H 882 3-ClPh 2-CH.sub.3 OPh 0 H H H H H 883 4-ClPh 2-CH.sub.3 OPh 0 H H H H H 884 2,4-Cl.sub.2Ph 2-CH.sub.3 OPh 0 H H H H H 885 4-BrPh 2-CH.sub.3 OPh 0 H H H H H 886 2-CF.sub.3Ph 2-CH.sub.3 OPh 0 H H H H H 887 3-CF.sub.3Ph 2-CH.sub.3 OPh 0 H H H H H 888 4-CF.sub.3Ph 2-CH.sub.3  OPh 0 H H H H H 889 Ph 4-CF.sub.3 OPh 0 H H H H H 890 2-FPh 4-CF.sub.3  P Oh 0 H H H H H 891 3-FPh 4-CF.sub.3 OPh 0 H H H H H 892 4-FPh 4-CF.sub.3 OPh 0 H H H H H 893 2,4-F.sub.2Ph 4-CF.sub.3 OPh 0 H H H H H 894 2-ClPh 4-CF.sub.3 OPh 0 H H H H H 895 3-ClPh 4-CF.sub.3 OPh 0 H H H H H 896     P 4-Clh 4-CF.sub.3 OPh 0 H H H H H 897 2,4-Cl.sub.2Ph 4-CF.sub.3 OPh 0 H H H H H 898 4-BrPh 4-CF.sub.3 OPh 0 H H H H H 899 2-CF.sub.3Ph 4-CF.sub.3  P Oh 0 H H H H H 900 3-CF.sub.3Ph 4-CF.sub.3                               P  OPh 0 H H H H H 901 4-CF.sub.3h 4-CF.sub.3 OPh 0 H H H H H 902 2-FPh 3,4-Cl.sub.2Ph 0 H H H H H 903 3-FPh 3,4-Cl.sub.2Ph 0 H H H H H 904 2,4-F.sub.2Ph 3,4-Cl.sub.2Ph 0 H H H H H 905 3-ClPh 3,4-Cl.sub.2Ph 0 H H H H H 110-11 906 2,4-Cl.sub.2Ph 3,4-Cl.sub.2Ph 0 H H H H H 907 4-BrPh 3,4-Cl.sub.2Ph 0 H H H H H 908 2-CF.sub.3Ph 3,4-Cl.sub.2Ph 0 H H H H H 909 3-CF.sub.3Ph 3,4-Cl.sub.2Ph 0 H H H H H 910 4-CF.sub.3Ph 3,4-Cl.sub.2P h 0 H H H H H 911 Ph 2,5-F.sub.2Ph 0 H H H H H 912 2-FPh 2,5-F.sub.2Ph 0 H H H H H 913 3-FPh 2,5-F.sub.2Ph 0 H H H H H 914 4-FPh 2,5-F.sub.2Ph 0 H H H H H 915 2,4-F.sub.2Ph 2,5-F.sub.2Ph 0 H H H H H 916 2-ClPh 2,5-F.sub.2Ph 0 H H H H H 917 3-ClPh 2,5-F.sub.2Ph 0 H H H H H 918 4-ClPh 2,5-F.sub.2Ph 0 H H H H H 919 2,4-Cl.sub.2Ph 2,5-F.sub.2Ph 0 H H H H H 920 4-BrPh 2,5-F.sub.2Ph 0 H H H H H 921 2-CF.sub.3Ph 2,5-F.sub.2Ph  0 H H H H H 922 3-CF.sub.3Ph 2,5-F.sub.2Ph 0 H H H H H 923 4-CF.sub.3Ph 2,5-F.sub.2Ph 0 H H H H H 924 Ph 2,5-Cl.sub.2Ph 0 H H H H H 925 2-FPh 2,5-Cl.sub.2Ph 0 H H H H H 926 3-FPh 2,5-Cl.sub.2Ph 0 H H H H H 927 4-FPh 2,5-Cl.sub.2Ph 0 H H H H H 928 2,4-F.sub.2Ph 2,5-Cl.sub.2Ph 0 H H H H H 929 2-ClPh 2,5-Cl.sub.2Ph 0 H H H H H 930 3-ClPh 2,5-Cl.sub.2Ph 0 H H H H H 931 4-ClPh 2,5-Cl.sub.2Ph 0 H H H H H 932 2,4-Cl.sub.2Ph 2,5-Cl.sub.2Ph 0 H H H H H 933 4-BrPh 2,5-Cl.sub.2Ph 0 H H H H H 934 2-CF.sub.3Ph 2,5-Cl.sub.2Ph 0 H H H H H 935 3-CF.sub.3Ph 2,5-Cl.sub.2Ph 0 H H H H H 936 4-CF.sub.3Ph 2,5-Cl.sub.2Ph 0 H H H H H 937 Ph 2,4,6-F.su b.3Ph 0 H H H H H 938 2-FPh 2,4,6-F.sub.3Ph 0 H H H H H 939 3-FPh 2,4,6-F.sub.3Ph 0 H H H H H 940 4-FPh 2,4,6-F.sub.3Ph 0 H H H H H 941 2,4-F.sub.2Ph 2,4,6-F.sub.3Ph 0 H H H H H 942 2-Cl Ph 2,4,6-F.sub.3Ph 0 H H H H H 943 3-ClPh 2,4,6-F.sub.3Ph 0 H H H H H 944 4-ClPh 2,4,6-F.sub.3P h 0 H H H H H 945 2,4-Cl.sub.2Ph 2,4,6-F.sub.3Ph 0 H H H H H 946 4-BrPh 2,4,6-F.sub.3Ph 0 H H H H H 947 2-CF.sub.3Ph 2,4,6-F.sub.3Ph 0 H H H H H 948 3-CF.sub.3Ph 2,4,6-F.sub.3Ph 0 H H H H H 949 4-CF.sub.3Ph 2,4,6-F.sub .3Ph 0 H H H H H 950 Ph 2,4,5-F.sub.3Ph 0 H H H H H 951 2-FPh 2,4,5-F.sub .3Ph 0 H H H H H 952 3-FPh 2,4,5-F.sub.3Ph 0 H H H H H 953 4-FPh 2.4.5-F.sub.3Ph 0 H H H H H 954 2,4-F.sub.2Ph 2,4,5-F.sub.3Ph 0 H H H H H 955 2-ClPh 2,4,5-F.sub.3Ph 0 H H H H H 956 3-ClPh 2,4,5-F.sub.3Ph 0 H H H H H 957 4-ClPh 2,4,5-F.sub.3Ph 0 H H H H H 958 2,4-Cl.sub.2Ph 2,4,5-F.sub. 3Ph 0 H H H H H 959 4-BrPh 2,4,5-F.sub.3Ph 0 H H H H H 960 2-CF.sub.3Ph 2,4,5-F.sub.3Ph 0 H H H H H 961 3-CF.sub.3Ph 2,4,5-F.sub.3Ph  0 H H H H H 962 4-CF.sub.3Ph 2,4,5-F.sub.3Ph 0 H H H H H 963 2-FPh 2-Cl-4-FPh 0 H H H H H 964 3-FPh 2-Cl-4-FPh 0 H H H H H 965 2,4-F.sub.2Ph  2-Cl-4-FPh 0 H H H H H 966 3-ClPh 2-Cl-4-FPh 0 H H H H H 967 2,4-Cl.sub. 2Ph 2-Cl-4-FPh 0 H H H H H 968 4-BrPh 2-Cl-4-FPh 0 H H H H H 969 2-CF.sub.3Ph 2-Cl-4-FPh 0 H H H H H 970 3-CF.sub.3Ph 2-Cl-4-FPh 0 H H H H H 971 4-CF.sub.3Ph 2-Cl-4-FPh 0 H H H H H 972 Ph 4-F-1-naphthyl 0 H H H H H 973 2-FPh 1-naphthyl 0 H H H H H 974 3-FPh 1-naphthyl 0 H H H H H 975 4-FPh 1-naphthyl 0 H H H H H 976 2,4-F.sub.2Ph 1-naphthyl 0 H H H H H 977 2-ClPh 1-naphthyl 0 H H H H H 978 3-ClPh 1-naphthyl 0 H H H H H 979 4-ClPh 1-naphthyl 0 H H H H H 980 2,4-Cl.sub.2Ph 1-naphthyl 0 H H H H H 981 4-BrPh 1-naphthyl 0 H H H H H 982 2-CF.sub.3Ph 1-naphthyl 0 H H H H H 983 3-CF.sub.3Ph 1-naphthyl 0 H H H H H 984 4-CF.sub.3Ph 1-naphthyl  0 H H H H H 985 Ph 6-Cl-2-naphthyl 0 H H H H H 986 2-FPh 2-naphthyl 0 H H H H H 987 3-FPh 2-naphthyl 0 H H H H H 988 4-FPh 2-naphthyl 0 H H H H H 989 2,4-F.sub.2Ph 2-naphthyl 0 H H H H H 990 2-ClPh 2-naphthyl 0 H H H H H 991 3-ClPh 2-naphthyl 0 H H H H H 992 4-ClPh 2-naphthyl 0 H H H H H 993 2,4,-Cl.sub.2Ph 2-naphthyl 0 H H H H H 994 4-BrPh 2-naphthyl 0 H H H H H 995 2-CF.sub. 3Ph 2-naphthyl 0 H H H H H 996 3-CF.sub.3Ph 2-naphthyl 0 H H H H H 997 4-CF.sub.3Ph 2-naphthyl 0 H H H H H 998 Ph PhCH.sub.2 0 H H H H H 999 2-FPh PhCH.sub.2 0 H H H H H 1000 3-FPh PhCH.sub.2 0 H H H H H 1001 4-FPh PhCH.sub.2 0 H H H H H 1002 2,4-F.sub.2Ph PhCH.sub.2 0 H H H H H 1003 2-ClPh PhCH.sub.2 0 H H H H H 1004 3-ClPh PhCH.sub.2 0 H H H H H 1005 4-ClPh PhCH.sub.2 0 H H H H H 1006 2,4-Cl.sub.2Ph PhCH.sub.2 0 H H H H H 1007 4-BrPh PhCH.sub.2 0 H H H H H 1008 2-CF.sub.3Ph PhCH.sub.2 0 H H H H H 1009 3-CF.sub.3Ph PhCH.sub.2 0 H H H H H 1010 4-CF.sub.3Ph PhCH.sub.2 0 H H H H H 1011 Ph PhCH(CH.sub.3) 0 H H H H H 1012 2-FPh PhCH(CH.sub.3) 0 H H H H H 1013 3-FPh PhCH(CH.sub.3) 0 H H H H H 1014 4-FPh PhCH(CH.sub.3) 0 H H H H H 1015 2,4-F.sub.2Ph PhCH(CH.sub. 3) 0 H H H H H 1016 2-ClPh PhCH(CH.sub.3) 0 H H H H H 1017 3-ClPh PhCH(CH.sub.3) 0 H H H H H 1018 4-ClPh PhCH(CH.sub.3) 0 H H H H H 1019 2.4-Cl.sub.2Ph PhCH(CH.sub.3) 0 H H H H H 1020 4-BrPh PhCH(CH.sub.3) 0 H H H H H 1021 2-CF.sub.3Ph PhCH(CH.sub.3) 0 H H H H H 1022 3-CF.sub.3Ph PhCH(CH.sub.3) 0 H H H H H 1023 4-CF.sub.3Ph PhCH(CH.sub.3) 0 H H H H H 1024 Ph PhC(CH.sub.3).sub.2 0 H H H H H 1025 2-FPh PhC(CH.sub.3).sub.2 0 H H H H H 1026 3-FPh PhC(CH.sub.3).sub.2 0 H H H H H 1027 4-FPh PhC(CH.su b.3).sub.2 0 H H H H H 1028 2,4-F.sub.2Ph PhC(CH.sub.3).sub.2 0 H H H H H 1029 2-ClPh PhC(CH.sub.3).sub.2 0 H H H H H 1030 3-ClPh PhC(CH.sub.3).s ub.2 0 H H H H H 1031 4-ClPh PhC(CH.sub.3).sub.2 0 H H H H H 1032 2,4-Cl.sub.2Ph PhC(CH.sub.3).sub.2 0 H H H H H 1033 4-BrPh PhC(CH.sub.3). sub.2 0 H H H H H 1034 2-CF.sub.3Ph PhC(CH.sub.3).sub.2 0 H H H H H 1035 3-CF.sub.3Ph PhC(CH.sub.3).sub.2 0 H H H H H 1036 4-CF.sub.3Ph PhC(CH.sub .3).sub.2 0 H H H H H 1037 Ph 4-ClPhC(CH.sub.3).sub.2 0 H H H H H 1038 2-FPh 4-ClPhC(CH.sub.3).sub.2 0 H H H H H 1039 3-FPh 4-ClPhC(CH.sub.3).su b.2 0 H H H H H 1040 4-FPh 4-ClPhC(CH.sub.3).sub.2 0 H H H H H (oil).sup. x 1041 2,4-F.sub. 2Ph 4-ClPhC(CH.sub.3).sub.2 0 H H H H H 1042 2-ClPh 4-ClPhC(CH.sub.3).sub.2 0 H H H H H 1043 3-ClPh 4-ClPhC(CH.sub.3).sub.2 0 H H H H H 1044 4-ClPh 4-ClPhC(CH.sub.3).sub.2 0 H H H H H 1045 2,4-Cl.sub.2Ph 4-ClPhC(CH.sub.3).sub.2 0 H H H H H 1046 4-BrPh 4-ClPhC(CH .sub.3).sub.2 0 H H H H H 1047 2-CF.sub.3Ph 4-ClPhC(CH.sub.3).sub.2 0 H H H H H 1048 3-CF.sub.3Ph 4-ClPhC(CH.sub.3).sub.2 0 H H H H H 1049 4-CF.sub.3Ph 4-ClPhC(CH.sub.3).sub.2 0 H H H H H 1050 Ph 2-thienyl 0 H H H H H 127-129 1051 2-FPh 2-thienyl 0 H H H H H 1052 3-FPh 2-thienyl 0 H H H H H 1053 4-FPh 2-thienyl 0 H H H H H 125-134 1054 2,4-F.sub.2Ph 2-thienyl 0 H H H H H 1055 2-ClPh 2-thienyl 0 H H H H H 1056 3-ClPh 2-thienyl 0 H H H H H 110 1057 4-ClPh 2-thienyl 0 H H H H H 141-143 1058 2,4-Cl.sub.2Ph 2-thienyl 0 H H H H H (oil).sup.y 1059 4-BrPh 2-thienyl 0 H H H H H 1060 2-CF.sub.3Ph 2-thienyl 0 H H H H H 1061 3-CF.sub.3Ph 2-thienyl 0 H H H H H 1062 4-CF.sub.3Ph 2-thienyl 0 H H H H H 1063 Ph 3-thienyl 0 H H H H H 1064 2-FPh 3-thienyl 0 H H H H H 1065 3-FPh 3-thienyl 0 H H H H H 1066 4-FPh 3-thienyl 0 H H H H H 1067 2,4-F.sub.2Ph  3-thienyl 0 H H H H H 1068 2-ClPh 3-thienyl 0 H H H H H 1069 3-ClPh 3-thienyl 0 H H H H H 1070 4-ClPh 3-thienyl 0 H H H H H 1071 2,4-Cl.sub.2P h 3-thienyl 0 H H H H H 1072 4-BrPh 3-thienyl 0 H H H H H 1073 2-CF.sub.3P h 3-thienyl 0 H H H H H 1074 3-CF.sub.3Ph 3-thienyl 0 H H H H H 1075 4-CF.sub.3Ph 3-thienyl 0 H H H H H 1076 2-FPh 2-Cl-3-thienyl 0 H H H H H 1077 3-FPh 2-Cl-3-thienyl 0 H H H H H 1078 2,4-F.sub.2Ph 2-Cl-3-thienyl 0 H H H H H 1079 3-ClPh 2-Cl-3-thienyl 0 H H H H H 1080 2,4-Cl.sub.2Ph 2-Cl-3-thienyl 0 H H H H H 1081 4-BrPh 2-Cl-3-thienyl 0 H H H H H 1082 2-CF.sub.3Ph 2-Cl-3-thienyl 0 H H H H H 1083 3-CF.sub.3Ph 2-Cl-3-thienyl 0 H H H H H 1084 4-CF.sub.3Ph 2-Cl-3-thienyl 0 H H H H H 1085 2-FPh 5-Cl-2-thienyl 0 H H H H H 1086 3-FPh 5-Cl-2-thienyl 0 H H H H H 1087 2,4-F.sub.2Ph 5-Cl-2-thienyl 0 H H H H H 1088 3-ClPh 5-Cl-2-thienyl 0 H H H H H 111-112 1089 2,4-Cl.sub.2Ph 5-Cl-2-thienyl 0 H H H H H 103-106 1090 4-BrPh 5-Cl-2-thienyl 0 H H H H H 1091 2-CF.sub.3Ph 5-Cl-2-thienyl 0 H H H H H 1092 3-CF.sub.3Ph 5-Cl-2-thienyl 0 H H H H H (oil).sup.z 1093 4-CF.sub.3Ph 5-Cl-2-thienyl 0 H H H H H 1094 Ph 2,5-Cl.sub.2 -3-thienyl 0 H H H H H (oil).sup.aa 1095 2-FPh 2,5-Cl.sub.2 -3-thienyl 0 H H H H H 1096 3-FPh 2,5-Cl.sub.2 -3-thienyl 0 H H H H H 1097 4-FPh 2,5-Cl.sub.2  -3-thienyl 0 H H H H H 60-62 1098 2,4-F.sub.2Ph 2,5-Cl.sub.2 -3-thienyl 0 H H H H H 1099 2-ClPh 2,5-Cl.sub.2 -3-thienyl 0 H H H H H (oil).sup.ab 1100 3-ClPh 2,5-Cl.sub.2 -3-thienyl 0 H H H H H 54-57 1101 4-ClPh 2,5-Cl.sub.2 -3-thienyl 0 H H H H H (oil).sup.ac 1102 2,4-Cl.sub.2Ph 2,5-Cl.sub.2  -3-thienyl 0 H H H H H (oil).sup.ad 1103 4-BrPh 2,5-Cl.sub.2 -3-thienyl 0 H H H H H 1104 2-CF.sub.3Ph 2,5-Cl.sub.2 -3-thienyl 0 H H H H H 1105 3-CF.sub.3Ph 2,5-Cl.sub.2 -3-thienyl 0 H H H H H (oil).sup.ae 1106 4-CF.sub.3Ph 2,5-Cl.sub.2  -3-thienyl 0 H H H H H 1107 Ph 5-bromo-2-thienyl 0 H H H H H 1108 2-FPh 5-bromo-2-thienyl 0 H H H H H 1109 3-FPh 5-bromo-2-thienyl 0 H H H H H 1110 4-FPh 5-bromo-2-thienyl 0 H H H H H 1111 2,4-F.sub.2Ph 5-bromo-2-thi enyl 0 H H H H H 1112 2-ClPh 5-bromo-2-thienyl 0 H H H H H 1113 3-ClPh 5-bromo-2-thienyl 0 H H H H H 1114 4-ClPh 5-bromo-2-thienyl 0 H H H H H 1115 2,4-Cl.sub.2Ph 5-bromo-2-thienyl 0 H H H H H 1116 4-BrPh 5-bromo-2-t hienyl 0 H H H H H 1117 2-CF.sub.3Ph 5-bromo-2-thienyl 0 H H H H H 1118 3-CF.sub.3 -Ph 5-bromo-2-thienyl 0 H H H H H 1119 4-CF.sub.3 -Ph 5-bromo-2-thienyl 0 H H H H H 1120 Ph 2-pyridyl 0 H H H H H 1121 2-F-Ph 2-pyridyl 0 H H H H H 1122 3-F-Ph 2-pyridyl 0 H H H H H 1123 2,4-F.sub.2P h 2-pyridyl 0 H H H H H 1124 2-Cl-Ph 2-pyridyl 0 H H H H H 1125 3-Cl-Ph 2-pyridyl 0 H H H H H 1126 4-Cl-Ph 2-pyridyl 0 H H H H H 1127 2,4-Cl.sub. 2Ph 2-pyridyl 0 H H H H H 1128 4-Br-Ph 2-pyridyl 0 H H H H H 1129 2-CF.sub.3Ph 2-pyridyl 0 H H H H H 1130 3-CF.sub.3Ph 2-pyridyl 0 H H H H H 1131 4-CF.sub.3Ph 2-pyridyl 0 H H H H H 1132 Ph 3-pyridyl 0 H H H H H 1133 2-F-Ph 2-pyridyl 0 H H H H H 1134 3-F-Ph 3-pyridyl 0 H H H H H 1135 4-F-Ph 3-pyridyl 0 H H H H H 1136 2,4-F.sub.2 -Ph 3-pyridyl 0 H H H H H 1137 2-Cl-Ph 3-pyridyl 0 H H H H H 1138 3-Cl-Ph 3-pyridyl 0 H H H H H 1139 4-Cl-Ph 3-pyridyl 0 H H H H H 1140 2,4-Cl.sub.2 -Ph 3-pyridyl 0 H H H H H 1141 4-Br-Ph 3-pyridyl 0 H H H H H 1142 2-CF.sub.3 -Ph 3-pyridyl 0 H H H H H 1143 3-CF.sub.3 -Ph 3-pyridyl 0 H H H H H 1144 4-CF.sub.3Ph 3-pyridyl 0 H H H H H 1145 Ph 4-pyridyl 0 H H H H H 1146 2-F-Ph 4-pyridyl  0 H H H H H 1147 3-F-Ph 4-pyridyl 0 H H H H H 1148 2,4-F.sub.2Ph 4-pyridyl 0 H H H H H 1149 2-Cl-Ph 4-pyridyl 0 H H H H H 1150 3-Cl-Ph 4-pyridyl 0 H H H H H 1151 4-Cl-Ph 4-pyridyl 0 H H H H H 1152 2,4-Cl.sub. 2Ph 4-pyridyl 0 H H H H H 1153 4-Br-Ph 4-pyridyl 0 H H H H H 1154 2-CF.sub.3Ph 4-pyridyl 0 H H H H H 1155 3-CF.sub.3Ph 4-pyridyl 0 H H H H H 1156 4-CF.sub.3Ph 4-pyridyl 0 H H H H H 1157 Ph 2-Cl-3-pyridyl 0 H H H H H 1158 2-F-Ph 2-Cl-3-pyridyl 0 H H H H H 1159 3-F-Ph 2-Cl-3-pyridyl 0 H H H H H 1160 4-F-Ph 2-Cl-3-pyridyl 0 H H H H H 1161 2,4-F.sub.2Ph 2-Cl-3-pyridyl 0 H H H H H 1162 2-Cl-Ph 2-Cl-3-pyridyl 0 H H H H H 1163 3-Cl-Ph 2-Cl-3-pyridyl 0 H H H H H 1164 4-Cl-Ph 2-Cl-3-pyridyl 0 H H H H H 1165 2,4-Cl.sub.2Ph 2-Cl-3-pyridyl 0 H H H H H 1166 4-Br-Ph 2-Cl-3-pyri dyl 0 H H H H H 1167 2-CF.sub.3Ph 2-Cl-3-pyridyl 0 H H H H H 1168 3-CF.sub.3Ph 2-Cl-3-pyridyl 0 H H H H H 1169 4-CF.sub. 3Ph 2-Cl-3-pyridyl  0 H H H H H 1170 Ph 3-Cl-2-pyridyl 0 H H H H H 1171 2-F-Ph 3-Cl-2-pyridy l 0 H H H H H 1172 3-F-Ph 3-Cl-2-pyridyl 0 H H H H H 1173 4-F-Ph 3-Cl-2-pyridyl 0 H H H H H 1174 2,4-F.sub.2Ph 3-Cl-2-pyridyl 0 H H H H H 1175 2-Cl-Ph 3-Cl-2-pyridyl 0 H H H H H 1176 3-Cl-Ph 3-Cl-2-pyridyl 0 H H H H H 1177 4-Cl-Ph 3-Cl-2-pyridyl 0 H H H H H 1178 2,4-Cl.sub.2Ph 3-Cl-2-pyridyl 0 H H H H H 1179 4-Br-Ph 3-Cl-2-pyridyl 0 H H H H H 1180 2-CF.sub.3Ph 3-Cl-2-pyridyl 0 H H H H H 1181 3-CF.sub.3Ph 3-Cl-2-pyridyl 0 H H H H H 1182 4-CF.sub.3Ph 3-Cl-2-pyridyl 0 H H H H H 1183 2-F-Ph 5-Cl-2-pyridyl 0 H H H H H 1184 3-F-Ph 5-Cl-2-pyridyl 0 H H H H H 1185 2,4-F-Ph 5-Cl-2-pyridyl 0 H H H H H 1186 3-Cl-Ph 5-Cl-2-pyridyl 0 H H H H H 1187 2,4-Cl.sub.2Ph 5-Cl-2-pyridyl 0 H H H H H 1188 4-Br-Ph 5-Cl-2-py ridyl 0 H H H H H 1189 2-CF.sub.3Ph 5-Cl-2-pyridyl 0 H H H H H 1190 3-CF.sub.3 Ph 5-Cl-2-pyridyl 0 H H H H H 1191 4-CF.sub.3Ph 5-Cl-2-pyridyl  0 H H H H H 1192 Ph 6-Cl-3-pyridyl 0 H H H H H 1193 2-F-Ph 6-Cl-3-pyridy l 0 H H H H H 1194 3-F-Ph 6-Cl-3-pyridyl 0 H H H H H 1195 4-F-Ph 6-Cl-3-pyridyl 0 H H H H H 1196 2,4-F.sub.2Ph 6-Cl-3-pyridyl 0 H H H H H 1197 2-Cl-Ph 6-Cl-3-pyridyl 0 H H H H H 1198 3-Cl-Ph 6-Cl-3-pyridyl 0 H H H H H 1199 4-Cl-Ph 6-Cl-3-pyridyl 0 H H H H H 1200 2,4-Cl.sub.2Ph 6-Cl-3-pyridyl 0 H H H H H 1201 4-Br-Ph 6-Cl-3-pyridyl 0 H H H H H 1202 2-CF.sub.3Ph 6-Cl-3-pyridyl 0 H H H H H 1203 3-CF.sub.3Ph 6-Cl-3-pyridyl 0 H H H H H 1204 4-CF.sub.3Ph 6-Cl-3-pyridyl 0 H H H H H 1205 2-thienyl 2-thienyl 0 H H H H H 1206 3-thienyl 2-thienyl 0 H H H H H 1207 2-Cl-3-th ienyl 2-thienyl 0 H H H H H 1208 5-Cl-2-thienyl 2-thienyl 0 H H H H H 1209 2,5-Cl.sub.2 -3-thienyl 2-thienyl 0 H H H H H 1210 2-thienyl 3-thienyl 0 H H H H H 1211 3-thienyl 3-thienyl 0 H H H H H 1212 2-Cl-3-th ienyl 3-thienyl 0 H H H H H 1213 5-Cl-2-thienyl 3-thienyl 0 H H H H H 1214 2,5-Cl.sub.2  -thienyl 3-thienyl 0 H H H H H 1215 2-thienyl 2-Cl-3-thienyl 0 H H H H H 1216 3-thienyl 2-Cl-3-thienyl 0 H H H H H 1217 2-Cl-3-thienyl 2-Cl-3-th ienyl 0 H H H H H 1218 5-Cl-2-thienyl 2-Cl-3-thienyl 0 H H H H H 1219 2,5-Cl.sub.2 -3-thienyl 2-Cl-3-thienyl 0 H H H H H 1220 2-thienyl 5-Cl-3-thienyl 0 H H H H H 1221 3-thienyl 5-Cl-3-thienyl 0 H H H H H 1222 2-Cl-3-thienyl 5-Cl-3-thienyl 0 H H H H H 1223 5-Cl-2-thienyl 5-Cl-3-thienyl 0 H H H H H 1224 2,5-Cl.sub.2 -3-thienyl 5-Cl-3-thienyl 0 H H H H H 1225 2-thienyl 2,5-Cl.sub.2 -3-thienyl 0 H H H H H 1226 3-thienyl 2,5-Cl.sub.2 -3-thienyl 0 H H H H H 1227 2-Cl-3-thienyl 2,5-Cl.sub.2 -3-thienyl 0 H H H H H 1228 5-Cl-2-thienyl 2,5-Cl.sub.2 -3-thienyl 0 H H H H H 1229 2,5-Cl.sub.2 -3-thienyl 2,5-Cl.sub.2 -3-thienyl 0 H H H H H 1230 thienyl 5-F-2-thienyl 0 H H H H H 1231 3-pyridyl 5-Cl-2-pyridyl 0 H H H H H 1232 5-Cl-2-pyridyl 5-Cl-2-pyridyl 0 H H H H H 1233 4-pyridyl 5-Cl-2-pyridyl 0 H H H H H 1234 2-Cl-3-pyridyl  5-Cl-2-pyridyl 0 H H H H H 1235 2-pyridyl 5-Cl-2-pyridyl 0 H H H H H 1236 4-F-Ph 4-F-Ph 0 H H H C.sub.2 H.sub.5 H 1237 4-F-Ph 4-F-Ph 0 H H H  n --C.sub.3 H.sub.7 H 1238 4-F-Ph 4-F-Ph 0 H H H -n-C.sub.4 H.sub.9 H 1239 4-F-Ph 4-F-Ph 0 H H H .sub.-i-C.sub.3 H.sub.7 H 1240 4-F-Ph 4-F-Ph 0 H H H .sub.-s-C.sub.4 H.sub.9 H 1241 2-Cl-Ph 4-Cl-Ph 0 H H H C.sub.2 H.sub.5 H 1242 2-Cl-Ph 4-Cl-Ph 0 H H H -n-C.sub.3 H.sub.7 H 1243 2-Cl-Ph 4-Cl-Ph 0 H H H -n-C.sub.4  H.sub.9 H 1244 2-Cl-Ph 4-Cl-Ph 0 H H H .sub.-i-C.sub.3 H.sub.7 H 1245 2-Cl-Ph 4-Cl-Ph 0 H H H .sub.-s-C.sub.4  H.sub.9 H 1246 4-Cl-Ph 2,4-Cl.sub.2 -Ph 0 H H H C.sub.2 H.sub.5 H 1247 4-Cl-Ph 2,4-Cl.sub.2 -Ph 0 H H H .sub.-n-C.sub.3 H.sub.7 H 1248 4-Cl-Ph 2,4-Cl.sub.2 -Ph 0 H H H .sub.-n-C.sub.4  H.sub.9 H 1249 4-Cl-Ph 2,4-Cl.sub.2 -Ph 0 H H H .sub.-i-C.sub.3 H.sub.7 H 1250 4-Cl-Ph 2,4-Cl.sub.2 -Ph 0 H H H .sub.-s-C.sub.4 H.sub.9 H 1251 Ph 4-F-Ph 0 H H H C.sub.2 H.sub.5 H 1252 Ph 4-F-Ph 0 H H H -n-C.sub.3 H.sub.7 H 1253 Ph 4-F-Ph 0 H H H -n-C.sub.4 H.sub.9 H 1254 Ph 4-F-Ph 0 H H H .sub.-i-C.sub.3 H.sub.7 H 1255 Ph 4-F-Ph 0 H H H .sub.-s-C.sub.4 H.sub.9 H 1256 4-F-Ph 4-F-Ph 0 H H H CH.sub.3 H 1257 4-F-Ph 4-F-Ph 0 H H H CH.sub.3 CH.sub.3 1258 4-F-Ph 4-F-Ph 0 H H H F H 166-167 1259 4-F-Ph 4-F-Ph 0 H H H F CH.sub.3 1260 4-F-Ph 4-F-Ph 0 H H H F F 145-147 1261 4-Cl-Ph 2,4-Cl.sub.2Ph 0 H H H CH.sub.3 H 1262 4-Cl-Ph 2,4-Cl.sub.2Ph 0 H H H CH.sub.3 CH.sub.3 1263 4-Cl-Ph 2,4-Cl.sub.2Ph 0 H H H F H 1264 4-Cl-Ph 2,4-Cl.sub.2Ph 0 H H H F CH.sub.3 1265 4-Cl-Ph 2,4-Cl.sub.2Ph 0 H H H F F 1266 2-Cl-Ph 4-Cl-Ph 0 H H H CH.sub.3 H 1267 2-Cl-Ph 4-Cl-Ph 0 H H H CH.sub.3 CH.sub.3 1268 2-Cl-Ph 4-Cl-Ph 0 H H H F H 1269 2-Cl-Ph 4-Cl-Ph 0 H H H F CH.sub.3 1270 2-Cl-Ph 4-Cl-Ph 0 H H H F F 1271 Ph 4-F-Ph 0 H H H CH.sub.3 H 1272 Ph 4-F-Ph 0 H H H CH.sub.3 CH.sub.3 1273 Ph 4-F-Ph 0 H H H F H 1274 Ph 4-F-Ph 0 H H H F CH.sub.3 1275 Ph 4-F-Ph 0 H H H F F 1997 Ph 4-.sub.-t-Bu-Ph 0 H H H H H 112-114 1998 4-F-Ph 2,6-F.sub.2 -Ph 0 H H H H H 110-116 1999 4-F-Ph 3-CH.sub.3 -4-Cl-Ph 0 H H H H H 127.5-129   2000 4-F-Ph 4-.sub.-t-BuPh 0 H H H H H 105-107 2001 4-F-Ph 4-CN-Ph 0 H H H H H 137-139 2002 4-F-Ph CF.sub.3 0 H H H H H (oil).sup.ag 2003 2-CF.sub.3Ph 3-CF.sub.3Ph 0 H H H H H (oil).sup.ah 2004 4-CH.sub.3Ph 2-F-Ph 0 H H H H H 115-118 2005 4-CH.sub.3Ph 2-Cl-4-F-Ph 0 H H H H H 111-116 2006 Ph 2,4-F.sub.2Ph 0 H H CH.sub.3 H H 67-72 2007 Ph 4-Cl-Ph 0 H H CH.sub.3 H H 110.5-111   2008 4-F-Ph 2-F-Ph 0 H H CH.sub.3 H H 67-72 2009 4-F-Ph 2,4-F.sub.2 -Ph 0 H H CH.sub.3 H H (oil).sup.ai 2010 2-Cl-3-pyridyl, N-oxide 4-Cl-Ph 0 H H H H H (HCl salt).sup.aj 2011 4-Cl-3-pyridyl 2,4-F.sub.2 -Ph 0 H H H H H (oil).sup.ak 2012 4-Cl-3-pyridyl 4-Cl-Ph 0 H H H H H 172-174 2013 4-Cl-3-pyridyl 2,4-Cl.sub.2 -Ph 0 H H H H H (oil).sup.al 2014 4-CH.sub.3 S-3-1 pyridyl 4-Cl-Ph 0 H H H H H 138-140 2015 2-Cl-4-pyridyl 4-Cl-Ph 0 H H H H H (2HCl salt 170-175) 2016 2-CH.sub.3 -Ph 2-Cl-4-F-Ph 0 H H H H .sup.a NMR: (CDCl.sub.3) δ 4.70 (q, J=14Hz, 2H), 4.90 (s, 1H), 5.40 (s, 1H), 5.55 (s, 1H), 6.8-7.0 (m, 4H), 7.2-7.4 (m, 4H), 7.8 (bs, 2H). .sup.b NMR: (CDCl.sub.3) δ 4.8 (q, 2H), 5.2 (s, 1H), 5.3 (s,1H), 5. (s, 1H), 6.9-7.6 (m, 8H), 7.8 (s, 1H), 8.1 (s, 1H). .sup.c NMR: (CDCl.sub.3) δ 4.70 (q, J=13Hz, 2H), 4.85 (s, 1H), 5.35 (s, 1H), 5.55 (s, 1H), 6.85-7.4 (m, 8H), 7.7 (s, H), 7.9 (s, 1H). .sup.d NMR: (CDCl.sub.3) δ 4.60 (q, J=12Hz, 2H), 5.0 (s, 1H), 5.40 (s, 1H), 5.55 (s, 1H), 6.8 (1/2 of ABq, J=10Hz, 2H), 7.00 (m, 2H), 7.3 (1/2 of ABq, J=10Hz, 2H), 7.45 (m, 2H), 7.80 (s, 1H), 7.85 (s, 1H). .sup.e NMR: (CDCl.sub.3) δ 4.6, 4.8 (ABq, J=14Hz, 2H), 4.9 (br s, 3H), 5.3 (s, 1H), 5.6 (s, 1H), 6.8 (d, 1H), 7.0 (m, 3H), 7.4 (m, 3H), 7.8 (s, 1H), 7.9 (s, 1H). .sup.f NMR: (CDCl.sub.3) δ 1.3 (s, 9H), 4.7 (q, 2H), 4.6 (s, 1H), 5.0 (s, 1H), 5.4 (s, 1H), 6.8-7.4 (9H), 7.8 (s, 1H). .sup.g NMR: (CDCl.sub.3) δ 4.7, 4.8 (ABq, J=12Hz, 2H), 6.7-7.5 (m, 14H), 7.9 (s, 1H), 8.0 (s, 1H). .sup.h NMR: (CDCl.sub.3) δ 3.45 (s, 3H), 4.75 (ABq, J=18Hz, 14Hz, 2H), 4.6 (m, 2H), 6.8-7.0 (m, 4H), 7.05-7.25 (m, 4H), 8.0 (s, 1H), 8.25 (s, 1H). .sup.i NMR: (CDCl.sub.3) δ 4.0 (dd, 14, 4Hz, 1H), 4.3 (dd, 14, 4Hz, 1H), 4.6 (d, 13Hz, 1H), 4.9 (d, 13Hz, 1H), 5.1 (d, 1H), 5.3 (d, 1H), 5.55 (s, 1H), 5.60 (s, 1H), 5.85 (m, 1H), 6.8-7.0 (m, 4H), 7.05-7.2 (m, 4H), 8.05 (s, 1H), 8.25 (s, 1H). .sup.j NMR: (CDCl.sub.3) δ 1.90 (s, 3H), 4.80 (1/2 of ABq, J=14Hz, 1H), 5.65 (1/2 of ABq, J= 14Hz, 1H), 5.55 (s, 1H), 5.60 (s, 1H), 6.75-7.0 (m, 4H), 7.0-7.2 (t, 2H), 7.25-7.4 (m, 2H), 7.35 (s, 1H), 7.85 (s, 1H). .sup.k NMR: (CDCl.sub.3) δ 4.03, 4.11 (ABq, J=11Hz, 2H), 4.25 (s, 1H, OH), 4.39 (s, 1H, OH), 4.54, 4.81 (ABq, J=14Hz, 2H), 5.31, 5.33 (2 sharp s, 1H each), 7.25-7.40 (m, 4H), 7.71 (s, 1H), 8.03 (s, 1H). .sup.l NMR: (CDCl.sub.3) δ 2.03 (s, 1H, OH), 4.0-4.2 (m, 2H), 4.57, 4.85 (ABq, J=15Hz, 2H), 5.3-5.35 (m, 2H), 5.7-5.9 (broad s, 1H, OH), 7.3-7.6 (m, 4H), 7.75 (s, 1H), 8.11 (s, 1H). .sup.m NMR: (CDCl.sub.3) δ 2.10 (s, 6H), 2.52, 3.03 (ABq, J=12Hz, 2H), 4.41, 4.78 (ABq, J=15Hz, 2H), 5.19 (s, 1H), 5.50 (s, 1H), 6.9-7.2 (m 2H), 7.4-7.6 (m, 2H), 7.80 (s, 1H), 8.36 (s, 1H). .sup.n NMR: (CDCl.sub.3) δ 2.11 (s, 6H), 2.61, 3.11 (ABq, J=12Hz, 2H), 4.50, 4.90 (ABq, J=13Hz, 2H), 5.13 (s, 1H), 5.50 (s, 1H), 7.50 (s, 4H), 7.86 (s, 1H), 8.14 (s, 1H). .sup.o NMR: (CDCl.sub.3) δ 2.13 (s, 3H), 2.19 (s, 3H), 2.5-3.1 (m, 2H), 4.44, 4.85 (ABq, J=14Hz, 2H), 5.0-5.5 (m, 2H), 7.3-7.8 (m, 9H), 7.97 (s, 1H), 8.32 (s, 1H, OH), 8.50 (s, 1H). .sup.p NMR: (CDCl.sub.3) δ 4.6 (d, 1/2 of ABq, 1H), 4.9 (d, 1/2 of ABq, 1H), 5.0 (s, 1H), 5.3 (two s, 2H), 6.9-7.6 (m, 9H), 7.8 (two s, 2H). .sup.q NMR: (CDCl.sub.3) δ 1.0 (t, 3H), 1.2 (s, 1H), 1.6 (m, 2H), 4.2 (ABq, 2H), 5.1 (s, 1H), 5.4 (s, 1H), 6.9-7.1 (m, 4H), 7.9 (s, 1H), 8. (s, 1H). .sup.r NMR: (CDCl.sub.3) δ 4.6 (AB, 2H), 4.6 (d, 1H), 5.3 (s, 1H), 5.5 (s, 1H), 7.2 (m, 1H), 7.6 (m, 7H), 7.7 (m, 1H), 7.7 (s, 1H), 7.8 (s, 1H). .sup.s NMR: (CDCl.sub.3) δ 4.6 (1/2 of AB, J=13, 1H), 5.0 (1/2 of AB, J=13, 1H), 5.2 (s, 1H), 5.3 (s, 1H), 5.4 (s, 1H), 7.0 (m, 2H), 7.2 (m 1H), 7.4 (m, 5H), 7.8 (s, 1H), 7.82 (s, 1H). .sup.t NMR: (CDCl.sub.3) δ 4.6 (1/2 of ABq, 1H), 5.3 (s), 5.4 (1/2 of ABq + s + br, 4H total), 7.1 (m, 1H), 7.3 (m, 1H), 7.5 (m, 5H), 7.8 (s 2H). .sup.u NMR: (CDCl.sub.3) δ 4.4 (1/2 of AB, 1H), 5.7 (1/2 of AB, 1H) 5.1 (s, 1H), 5.3 (s, 1H), 5.4 (s, 1H), 7.2 (m, 3H), 7.3 (m, 2H), 7.4 (d, 1H), 7.6 (m, 1H), 7.7 (s, 1H), 7.9 (s, 1H). .sup.v NMR: (CDCl.sub.3) δ 4.4 (s, 2H), 4.8 (s, 1H) 5.1 (s, 1H), 5. (s, 1H), 6.3 (d, 1H), 6.5 (d, 1H), 6.8-7.2 (m, 4H), 7.6 (s, 1H), 7.7 (s, 1H). .sup.w NMR: (CDCl.sub.3) δ 4.7 (dd, 2H), 5.4 (s, 1H), 5.6 (s, 1H), 6.7 (d, 1H), 7.0 (d, 1H), 7.2 (m), 8.0 (s, 1H), 8.2 (s, 1H). .sup.x NMR: (CDCl.sub.3) δ 1.6 (two s, 6H total), 4.3 (1/2 of ABq, 1H), 4.6 (1/2 of ABq, 1H), 5.0 (d, 1H), 5.2 (d, 1H), 5.3 (s, 1H), 6.7-7.6 (m, 8H), 7.9 (s, 1H), 8.1 (s, 1H). .sup.y NMR: (CDCl.sub.3 ) δ 4.7 (s, 2H), 5.3 (s, 1H), 5.8 (s, 1H), 6.9 (m, 3H), 7.1 (m, 1H), 7.2 (m, 1H), 7.4 (s, 1H), 7.9 (s, 1H), 8.1 (s, 1H). .sup.z NMR: (CDCl.sub.3) δ 4.6 (dd, 2H), 5.2 (s, 1H), 5.4 (s, 1H), 5.6 (s, 1H), 6.7 (d, 1H), 6.8 (d, 1H), 7.4-7.6 (m, 4H), 7.9 (s, 1H), 7.9 (s, 1H). .sup.aa NMR: (CDCl.sub.3) δ 4.6 (d, 1H), 5.0 (d, 1H), 5.2 (s, 1H), 5.34 (s, 1H), 5.4 (s, 1H), 6.8 (s, 1H), 7.2 (m, 5H), 7.9 (s, 2H). .sup.ab NMR: (CDCl.sub.3) δ 4.4 (d, 1H), 5.3 (d, 1H), 5.3 (s, 1H), 5.6 (s, 1H), 6.8 (s, 1H), 7.2-7.4 (m, 4H), 7.8 (s, 1H), 8.1 (s, 1H). .sup.ac NMR: (CDCl.sub.3) δ 4.6 (d, 1H), 5.1 (d, 1H), 5.3 (s, 1H), 5.35 (s, 1H), 5.45 (s, 1H), 6.8 (s, 1H), 7.2 (m, 4H), 7.9 (s, 1H), 8.1 (s 1H). .sup.ad NMR: (CDCl.sub.3) δ 4.6 (d, 1H), 5.3 (d, 1H), 5.3 (s, 1H), 5.6 (s, 1H), 6.8 (s, 1H), 7.2 (m, 2H), 7.4 (s, 1H), 7.9 (s, 1H), 8.1 (s, 1H). .sup.af NMR: (CDCl.sub.3) δ 4.7 (bs, 1H), 4.9 (bs, 1H), 5.33 (2s, 2H), 6.75 (d, 2H), 7.12 (m, 4H), 7.45 (s, 1H), 7.83 (s, 1H), 8.00 (s, 1H) 8.33 (d, 2H). .sup.ag NMR: (CDCl.sub.3) δ 4.6 (s, 2H), 5.4 (s, 1H), 5.5 (s, 1H), 5.8 (s, 1H), 6.8-7.0 (m, 3H), 7.3-7.4 (m, 1H), 8.0, 8.1 (two s, 2H). .sup.ah NMR: (CDCl.sub.3) δ 4.6 (ABq, 2H), 5.2 (s, OH), 5.3 (s, 1H) 5.4 (s, 1H), 7.1-7.7 (m, 8H), 7.7 (s, 1H), 7.8 (s, 1H). .sup.ai NMR: (CDCl.sub.3) δ 3.6 (s, 3H), 4.7-5.0 (ABq, 2H), 5.4 (s, 1H), 5.7 (s, 1H), 6.6-7.2 (m), 7.7 (s, 1H), 7.8 (s, 1H). .sup.aj NMR: (free base, CDCl.sub.3) δ 4.77 (s, 2H), 5.27 (s, 1H), 5.33 (s, 1H), 5.73 (s, 1H), 6.72 (d, 1H), 7.00 (t, 1H), 7.32 (ABq, 4H), 7.77 (s, 1H), 8.13 (s, 1H), 8.18 (d, 1H). .sup.ak NMR: (CDCl.sub.3) δ 4.63 (d, 1H), 5.03 (d, 1H), 5.30 (s, 1H), 5.42 (s, 1H), 5.50 (s, 1H), 6.75 (m, 2H), 7.23 (d, 1H), 7.43 (q, 1H) 7.67 (dd, 1H), 7.83 (s, 1H), 7.88 (s, 1H), 8.28 (d, 1H). .sup.al NMR: (CDCl.sub.3) δ 4.67 (d, 1H), 5.40 (s, 1H), 5.46 (s, 1H), 5.45 (d, 2H), 7.00-7.27 (m, 3H), 7.43 (d, 1H), 7.67-7.83 (m, 3H), 8.33 (d, 1H). .sup.am NMR: (CDCl.sub.3) δ 4.7 (1/2 of ABq, 1H), 5.0 (1/2 of ABq, 1H), 5.3 (s, 2H), 6.0 (s, 1H), 6.8 (m, 2H), 7.3-7.6 (m, 6H), 7.7 (s, 1H), 7.8 (d, 1H), 8.0 (s, 1H), 8.6 (d, 1H), 8.7 (s, 1H). .sup.an NMR: (CDCl.sub.3) δ 4.6 (1/2 of ABq, 1H), 5.0 (1/2 of ABq, 1H), 5.2-5.3 (three s, 3H), 6.8 (m, 2H), 7.5 (m, 6H), 7.8 (m, 3H), 8.6 (d 1H), 8.8 (s, 1H). 
    
     EXAMPLES 1276 and 1267a 
     Preparation of the (S)-enantiomer of Example 49 
     The compound of Example 49 (1.5 g) and 1.5 g of l-α-bromocamphor-π-sulfonic acid was dissolved in 75 ml of acetonitrile and refluxed for 2 hours. The solution was allowed to cool to ambient temperature and stand for 14 hours. Filtration of the resulting solids followed by recrystallization from an additional portion of acetonitrile, yielded 1.28 g of white solid, mp 216°-217°; [α] D   25  =-104° (C=1; DMSO). 
     The acetonitrile can be evaporated to yield the adduct having a (+)- rotation (Example 1276a). This compound can be recrystallized from an ether/acetone mixture to yield a solid, that on treatment with aqueous NaHCO 3  yields material identical by NMR to that of Example 49. 
     The solid was suspended in 50 ml of saturated NaHCO 3  solution and stirred vigorously until the evolution of gas ceased (1-2 hours). The mixture was extracted twice with 50 ml of CHCl 3 . The organic layers were combined, washed with brine, dried over Na 2  SO 4  and the solvent removed in vacuo. This yielded 750 mg of a white solid (Example 1276) having an &#39;H NMR identical to that of the compound of Example 49, mp=82°-83°; [α] D   25  =-62° (C=1; CHCl 3 ). 
     These compounds and other compounds which were resolved as described above are shown in Table 2. 
     
                                           TABLE 2__________________________________________________________________________ ##STR33##Ex.No.   A        B        n R R.sup.1                         R.sup.2                           R.sup.3                             R.sup.4                               M.P. °C.                                    [α].sub.D.sup.25__________________________________________________________________________1276  ##STR34##           ##STR35##                   O H H H H H  82-83                                    -62°1276a.sup.(1)  ##STR36##           ##STR37##                   O H H H H H  83-84                                    +60°1277.sup.(2)  ##STR38##           ##STR39##                   O H H H H H  60-61 (HCl salt 181-184                                    -67°1277a.sup.(1), (2)  ##STR40##           ##STR41##                   O H H H H H  60-62                                    +66°__________________________________________________________________________ *denotes chiral center .sup.(1) substitute dα-bromocamphor-π-sulfonic acid .sup.(2) use a 3 parts ether  1 part acetone mixture as solvent. 
    
     EXAMPLE 1278 
     Preparation of 2-(4-fluorophenyl)-3-phenyl-1(5-mercapto-1H-1,2,4-triazol-1-yl)-3-buten-1-ol 
     To a solution of 1.24 g (0.004 mol) of 2-(4-fluorophenyl)-3-phenyl-1-(1H-1,2,4-triazol-1-yl)-3-buten-2-ol in 15 mL of THF at -70° was added 5.2 mL (0.008 mol) of a 1.55M solution of n-butyllithium in hexanes over 5 minutes. After 30 minutes, 0.13 g (0.004 mol) of sulfur was added and the reaction mixture was allowed to warm to room temperature over 1 h, then quenched with 8 mL of 1N HCl. After pouring into saturated NH 4  Cl, the mixture was extracted with 2× ether and the combined organic layers were washed with brine, dried over Na 2  SO 4  and evaporated. The crude product was purified by flash chromatography using 2:13:85 methanol/ether/methylene chloride to give 0.85 g of the title compound, m.p. 54°-58°: NMR (CDCl 3 ) δ4.7 (ABq, 2H), 5.0 (s, 1H, OH), 5.3 (s, 1H, vinyl), 5.5 (s, 1H, vinyl), 7.0 (m, 4H), 7.2 (m, 3H), 7.5 (m, 2H), 7.7 (s, 1H, triazole proton), 12.5 (brs, 1H, SH); IR (methylene chloride) 3500-3000 (br), 1590, 1500, 1465, 1230, 1162, 1109, 825 cm -1  ; MS: highest m/e 341. 
     The compound shown in Table 3 with E being a bond were prepared or can be prepared by the methods described above. 
     
                                           TABLE 3*__________________________________________________________________________ ##STR42##Ex.No. A      B      R R.sup.1                 R.sup.2                   R.sup.4                     Q             M.P. °C.__________________________________________________________________________1278    Ph     4-FPh  H H H H SH            54-581279    Ph     Ph     H H H H SH1280    Ph     2-FPh  H H H H SH1281    Ph     2-ClPh H H H H SH1282    Ph     4-ClPh H H H H SH1283    Ph     2,4-F.sub.2Ph             H H H H SH1284    Ph     2,4-Cl.sub.2Ph             H H H H SH1285    2-FPh  Ph     H H H H SH1286    2-FPh  2-FPh  H H H H SH1287    2-FPh  4-FPh  H H H H SH1288    2-FPh  2-ClPh H H H H SH1289    2-FPh  4-ClPh H H H H SH1290    2-FPh  2,4-F.sub.2Ph             H H H H SH1291    2-FPh  2,4-Cl.sub.2Ph             H H H H SH1292    3-FPh  Ph     H H H H SH1293    3-FPh  2-FPh  H H H H SH1294    3-FPh  4-FPh  H H H H SH1295    3-FPh  2-ClPh H H H H SH1296    3-FPh  4-ClPh H H H H SH1297    3-FPh  2,4-F.sub.2Ph             H H H H SH1298    3-FPh  2,4-Cl.sub.2Ph             H H H H SH1299    4-FPh  Ph     H H H H SH1300    4-FPh  2-FPh  H H H H SH            144.5-1481301    4-FPh  4-FPh  H H H H SH1302    4-FPh  2-ClPh H H H H SH1303    4-FPh  4-ClPh H H H H SH1304    4-FPh  2,4-F.sub.2Ph             H H H H SH            (foam).sup.a1305    4-FPh  2,4-Cl.sub.2Ph             H H H H SH1306    2-ClPh Ph     H H H H SH1307    2-Cl Ph      2-FPh  H H H H SH1308    2-ClPh 4-FPh  H H H H SH1309    2-ClPh 2-ClPh H H H H SH1310    2-ClPh 4-ClPh H H H H SH1311    2-ClPh 2,4-F.sub.2Ph             H H H H SH1312    2-ClPh 2,4-Cl.sub.2Ph             H H H H SH1313    3-ClPh Ph     H H H H SH1314    3-ClPh 2-FPh  H H H H SH1315    3-ClPh 4-FPh  H H H H SH1316    3-ClPh 2-ClPh H H H H SH1317    3-ClPh 4-ClPh H H H H SH1318    3-ClPh 2,4-F.sub.2Ph             H H H H SH1319    3-ClPh 2,4-Cl.sub.2Ph             H H H H SH1320    4-ClPh Ph     H H H H SH1321    4-ClPh 2-FPh  H H H H SH1322    4-ClPh 4-FPh  H H H H SH1323    4-ClPh 2-ClPh H H H H SH1324    4-ClPh 4-ClPh H H H H SH1325    4-ClPh 2,4-F.sub.2Ph             H H H H SH1326    4-ClPh 2,4-Cl.sub.2Ph             H H H H SH1327    2-CF.sub.3Ph      Ph     H H H H SH1328    2-CF.sub.3Ph      2-FPh  H H H H SH1329    2-CF.sub.3Ph      4-FPh  H H H H SH1330    2-CF.sub.3Ph      2-ClPh H H H H SH1331    2-CF.sub.3Ph      4-ClPh H H H H SH1332    2-CF.sub.3Ph      2,4-F.sub.2Ph             H H H H SH1333    2-CF.sub.3Ph      2,4-Cl.sub.2Ph             H H H H SH1334    4-CF.sub.3Ph      Ph     H H H H SH1335    4-CF.sub.3Ph      2-FPh  H H H H SH1336    4-CF.sub.3Ph      4-FPh  H H H H SH1337    4-CF.sub.3Ph      2-ClPh H H H H SH1338    4-CF.sub.3Ph      4-ClPh H H H H SH1339    4-CF.sub.3Ph      2,4-F.sub.2Ph             H H H H SH1340    4-CF.sub.3Ph      2,4-Cl.sub.2Ph             H H H H SH1341    2,4-F.sub.2Ph      Ph     H H H H SH1342    2,4-F.sub.2Ph      2-FPh  H H H H SH1343    2,4-F.sub.2Ph      4-FPh  H H H H SH1344    2,4-F.sub.2Ph      2-ClPh H H H H SH1345    2,4-F.sub.2Ph      4-ClPh H H H H SH1346    2,4-F.sub.2Ph      2,4-F.sub.2Ph             H H H H SH1347    2,4-F.sub.2Ph      2,4-Cl.sub.2Ph             H H H H SH1348    2,4-Cl.sub.2Ph      Ph     H H H H SH1349    2,4-Cl.sub.2Ph      2-FPh  H H H H SH1350    2,4-Cl.sub.2Ph      4-FPh  H H H H SH1351    2,4-Cl.sub.2Ph      2-ClPh H H H H SH1352    2,4-Cl.sub.2Ph      4-ClPh H H H H SH1353    2,4-Cl.sub.2Ph      2,4-F.sub.2Ph             H H H H SH1354    2,4-Cl.sub.2Ph      2,4-Cl.sub.2Ph             H H H H SH1355    Ph     Ph     H H H H I1356    Ph     2-FPh  H H H H I1357    Ph     4-FPh  H H H H I1358    Ph     2-ClPh H H H H I1359    Ph     4-ClPh H H H H I1360    Ph     2,4-F.sub.2Ph             H H H H I1361    Ph     2,4-Cl.sub.2Ph             H H H H I1362    2-FPh  Ph     H H H H I1363    2-FPh  2-FPh  H H H H I1364    2-FPh  4-FPh  H H H H I1365    2-FPh  2-ClPh H H H H I1366    2-FPh  4-ClPh H H H H I1367    2-FPh  2,4-F.sub.2Ph             H H H H I1368    2-FPh  2,4-Cl.sub.2Ph             H H H H I1369    3-FPh  Ph     H H H H I1370    3-FPh  2-FPh  H H H H I1371    3-FPh  4-FPh  H H H H I1372    3-FPh  2-ClPh H H H H I1373    3-FPh  4-ClPh H H H H I1374    3-FPh  2,4-F.sub.2Ph             H H H H I1375    3-FPh  2,4-Cl.sub.2Ph             H H H H I1376    4-FPh  Ph     H H H H I1377    4-FPh  2-FPh  H H H H I               96-97.51378    4-FPh  4-FPh  H H H H I1379    4-FPh  2-ClPh H H H H I1380    4-FPh  4-ClPh H H H H I1381    4-FPh  2,4-F.sub.2Ph             H H H H I             (foam).sup.b1382    4-FPh  2,4-Cl.sub.2Ph             H H H H I1383    2-ClPh Ph     H H H H I1384    2-ClPh 2-FPh  H H H H I1385    2-ClPh 4-FPh  H H H H I1386    2-ClPh 2-ClPh H H H H I1387    2-ClPh 4-ClPh H H H H I1388    2-ClPh 2,4-F.sub.2Ph             H H H H I1389    2-ClPh 2,4-Cl.sub.2Ph             H H H H I1390    3-ClPh Ph     H H H H I1391    3-ClPh 2-FPh  H H H H I1392    3-ClPh 4-FPh  H H H H I1393    3-ClPh 2-ClPh H H H H I1394    3-ClPh 4-ClPh H H H H I1395    3-ClPh 2,4-F.sub.2Ph             H H H H I1396    3-ClPh 2,4-Cl.sub.2Ph             H H H H I1397    4-ClPh Ph     H H H H I1398    4-ClPh 2-FPh  H H H H I1399    4-ClPh 4-FPh  H H H H I1400    4-ClPh 2-ClPh H H H H I1401    4-ClPh 4-ClPh H H H H I1402    4-ClPh 2,4-F.sub.2Ph             H H H H I1403    4-ClPh 2,4-Cl.sub.2Ph             H H H H I1404    2-CF.sub.3Ph      Ph     H H H H I1405    2-CF.sub.3Ph      2-FPh  H H H H I1406    2-CF.sub.3Ph      4-FPh  H H H H I1407    2-CF.sub.3Ph      2-ClPh H H H H I1408    2-CF.sub.3Ph      4-ClPh H H H H I1409    2-CF.sub.3Ph      2,4-F.sub.2Ph             H H H H I1410    2-CF.sub.3Ph      2,4-Cl.sub.2Ph             H H H H I1411    4-CF.sub.3Ph      Ph     H H H H I1412    4-CF.sub.3Ph      2-FPh  H H H H I1413    4-CF.sub.3Ph      4-FPh  H H H H I1414    4-CF.sub.3Ph      2-ClPh H H H H I1415    4-CF.sub.3Ph      4-ClPh H H H H I1416    4-CF.sub.3Ph      2,4-F.sub.2Ph             H H H H I1417    4-CF.sub.3Ph      2,4-Cl.sub.2Ph             H H H H I1418    2,4-F.sub.2Ph      Ph     H H H H I1419    2,4-F.sub.2Ph      2-FPh  H H H H I1420    2,4-F.sub.2Ph      4-FPh  H H H H I1421    2,4-F.sub. 2Ph      2-ClPh H H H H I1422    2,4-F.sub.2Ph      4-ClPh H H H H I1423    2,4-F.sub.2Ph      2,4-F.sub.2Ph             H H H H I1424    2,4-F.sub.2Ph      2,4-Cl.sub.2Ph             H H H H I1425    2,4-Cl.sub.2Ph      Ph     H H H H I1426    2,4-Cl.sub.2Ph      2-FPh  H H H H I1427    2,4-Cl.sub.2Ph      4-FPh  H H H H I1428    2,4-Cl.sub.2Ph      2-ClPh H H H H I1429    2,4-Cl.sub.2Ph      4-ClPh H H H H I1430    2,4-Cl.sub.2Ph      2,4-F.sub.2Ph             H H H H I1431    2,4-Cl.sub.2Ph      2,4-Cl.sub.2Ph             H H H H I1432    Ph     2,4-F.sub.2Ph             H H H H SS1433    4-FPh  2-FPh  H H H H SS1434    4-FPh  2,4-F.sub.2Ph             H H H H SS1435    Ph     2,4-F.sub.2Ph             H H H H SSCH.sub.31436    4-FPh  2-FPh  H H H H SSCH.sub.31437    4-FPh  2,4-F.sub.2Ph             H H H H SSCH.sub.31438    Ph     2,4-F.sub. 2Ph             H H H H                      ##STR43##1439    4-FPh  2-FPh  H H H H                      ##STR44##1440    4-FPh  2,4-F.sub.2Ph             H H H H                      ##STR45##1441    Ph     2,4-F.sub.2Ph             H H H H                      ##STR46##1442    4-FPh  2-FPh  H H H H                      ##STR47##1443    4-FPh  2,4-F.sub.2Ph             H H H H                      ##STR48##1444    Ph     2,4-F.sub.2Ph             H H H H Cl1445    4-FPh  2-FPh  H H H H Cl1446    4-FPh  2,4-F.sub.2Ph             H H H H Cl1447    Ph     2,4-F.sub.2Ph             H H H H CHO1448    4-FPh  2-FPh  H H H H CHO1449    4-FPh  2,4-F.sub.2Ph             H H H H CHO1450    Ph     2,4-F.sub.2Ph             H H H H SCH.sub.2 CN1451    4-FPh  2-FPh  H H H H SCH.sub.2 CN  oil.sup.c1452    4-FPh  2,4-F.sub.2 Ph             H H H H SCH.sub.2 CN1453    Ph     2,4-F.sub.2Ph             H H H H SCH.sub.2 SCN1454    4-FPh  2-FPh  H H H H SCH.sub.2 SCN1455    4-FPh  2,4-F.sub.2Ph             H H H H SCH.sub.2 SCN1456    Ph     2,4-F.sub.2Ph             H H H H SCCl.sub.31457    4-FPh  2-FPh  H H H H SCCl.sub.31458    4-FPh  2,4-F.sub.2Ph             H H H H SCCl.sub.31459    Ph     4-FPh  H H H H S -n-Bu       semi-solid.sup.d1460    4-FPh  2-FPh  H H H H F1461    4-FPh  4-FPh  H H H H Br1462    4-FPh  2-FPh  H H H H                      ##STR49##1463    4-FPh  2-FPh  H H H H                      ##STR50##1464    4-FPh  2-FPh  H H H H                      ##STR51##1465    4-FPh  2-FPh  H H H H                      ##STR52##1466    4-FPh  2-F Ph H H H H SCF.sub.2 H1467    4-FPh  2-FPh  H H H H SCF.sub.2 CF.sub.2 H1468*    4-FPh  2-FPh  H H H H                      ##STR53##    (oil).sup.e1469*    4-FPh  2-FPh  H H H H                      ##STR54##    (oil).sup.f1470    4-FPh  2-FPh  H H H H                      ##STR55##1471    4-FPh  2-FPh  H H H H                      ##STR56##1472    4-FPh  2-FPh  H H H H                      ##STR57##1473    4-FPh  2-FPh  H H H H                      ##STR58##1474    4-FPh  2-FPh  H H H H                      ##STR59##1475    4-FPh  2-FPh  H H H H                      ##STR60##1476    4-FPh  2-FPh  H H H H                      ##STR61##1477    4-FPh  2-FPh  H H H H                      ##STR62##1478    4-FPh  2-FPh  H H H H                      ##STR63##1479    4-FPh  2-FPh  H H H H                      ##STR64##1480    4-FPh  2-FPh  H H H H                      ##STR65##1481    4-FPh  2-FPh  H H H H                      ##STR66##1482    4-FPh  2-FPh  H H H H                      ##STR67##1483    4-FPh  2-FPh  H H H H SCN1484    4-FPh  2-FPh  H H H H SSCH.sub.2 Ph1485    4-FPh  2-FPh  H H H H SS-allyl1486    4-FPh  2-FPh  H H H H SSPh__________________________________________________________________________ *All compounds in this table are compounds in which E is a bond except 1468 and 1469 in which E is an oxygen atom. .sup.a NMR: (CDCl.sub.3) δ 4.9 (s, 2H); 5.1 (s, 1H); 5.2 (s, 1H); 5.3 (s, 1H); 6.7 (m, 2H); 6.9 (m, 2H); 7.2 (m, 2H); 7.5 (m, 1H); 7.6 (s, 1H); 12.2 (brs, 1H). .sup.b NMR: (CDCl.sub.3) δ 4.7 (ABq, 2H); 5.3 (s, 2H); 5.8 (s, 1H); 6.7 (m, 2H); 6.9 (m, 2H); 7.3 (m, 2H); 7.5 (m, 1H); 7.8 (s, 1H). .sup.c NMR: (CDCl.sub.3) δ 3.8 (ABq, 2H); 4.7 (ABq, 2H); 5.2 (s, 1H); 5.3 (two s, 2H); 6.9-7.2 (m, 4H); 7.2-7.4 (m, 3H); 7.5 (m, 1H); 7.8 (s, 1H). .sup.d NMR: (CDCl.sub.3) δ 0.92 (t, 3H); 1.4-1.7 (m, 4H); 3.1 (t, 2H); 4.5 (ABq, 2H); 5.4 (two s, 2H); 5.8 (s, 1H); 7.0 (m, 4H); 7.2 (m, 3H); 7.5 (m, 2H); 7.8 (s, 1H). .sup.e NMR: (CDCl.sub.3) δ 2.7-3.5 (m, 2H); 4.3 (s, 1H); 4.4 (m, 2H); 5.2 (m, 2H); 6.8-7.4 (m, 8H); 7.9 (m, 1H). .sup.f NMR: (CDCl.sub.3) δ 2.7-3.4 (m, 2H); 4.2 (d, 1H); 4.5 (ABq, 2H); 5.3 (m, 2H); 6.8-7.4 (m, 8H); 7.9 (d, 1H). 
    
     EXAMPLE 1487 
     Preparation of 2,3-bis(4-fluorophenyl)-1-(1H-1,2,4-triazol-1-yl)-3,4-epoxy-2-butanol 
     2,3-Bis(4-fluorophenyl)-1-(1H-1,2,4-triazol-1-yl)-3-butene-2-ol (1.0 g) was dissolved in 50 ml of anhydrous benzene and stirred under nitrogen. To this solution was added 0.012 g of vanadium acetonylacetonate. The solution was then refluxed and tert-butyl hydroperoxide (0.44 g dissolved in 5 ml of anhydrous benzene) was added dropwise over 10 minutes. The reaction was refluxed for one additional hour and then cooled to ambient temperature. The benzene was removed in vacuo and the residue chromatographed on silica gel (2% MeOH/CH 2  Cl 2 ). This yielded a total of 650 mg of diastereomeric products in a 3:1 ratio. Further chromatography resulted in the separation of the diastereomers. The major isomer was a waxy white solid. NMR (CDCl 3  /TMS) δ2.60 (d, J=6 Hz, 1H); 3.48 (d, J=6 Hz, 1H); 4.70 (q, J=7 Hz, 2H); 5.25 (s, 1H); 6.8-7.3 (m, 8H); 7.55 (s, 1H); 7.90 (s, 1H). 
     The minor isomer was an amorphous white solid. NMR (CDCl 3  /TMS) δ2.55 (d, J=6H, 1H); 2.75 (d, J=6 Hz, 1H); 4.80, (q, J=7 Hz); 5.0 (s, 1H); 6.85-7.10 (m, 4H); 7.15-7.45 (m, 4H); 7.80 (s, 1H); 8.05 (s, 1H). 
     The epoxides shown in Table 4 were prepared or can be prepared by the method described in Example 1487. 
     
                                           TABLE 4__________________________________________________________________________ ##STR68##Ex.No.   A           B         n  R   R.sup.1                               R.sup.2 R.sup.3                                          R.sup.4                                              M.P.°C.__________________________________________________________________________1487   4-FPh       4-FPh     0  H   H   H       H  H   53-551488   4-FPh       2,4-Cl.sub.2Ph                    0  H   H   H       H  H1489   4-FPh       4-ClPh    0  H   H   H       H  H1490   4-FPh       2,4-F.sub.2Ph                    0  H   H   H       H  H   (semi-solid).sup.a1491   4-FPh       4-CF.sub.3Ph                    0  H   H   H       H  H1492   4-FPh       2-FPh     0  H   H   H       H  H   (110-119)1493   4-FPh       2-ClPh    0  H   H   H       H  H1494   4-FPh        -n-C.sub.4 F.sub.9                    0  H   H   H       H  H1495   3-FPh       4-FPh     0  H   H   H       H  H1496   3-FPh       2,4-Cl.sub.2Ph                    0  H   H   H       H  H1497   3-FPh       4-ClPh    0  H   H   H       H  H1498   3-FPh       2,4-F.sub.2Ph                    0  H   H   H       H  H1499   3-FPh       4-CF.sub.3Ph                    0  H   H   H       H  H1500   3-FPh       2-FPh     0  H   H   H       H  H1501   3-FPh       2-ClPh    0  H   H   H       H  H1502   3-FPh        -n-C.sub.4 F.sub.9                    0  H   H   H       H  H1503   4-ClPh      4-FPh     0  H   H   H       H  H1504   4-ClPh      2,4-Cl.sub.2Ph                    0  H   H   H       H  H1505   4-ClPh      4-ClPh    0  H   H   H       H  H1506   4-ClPh      2,4-F.sub.2Ph                    0  H   H   H       H  H1507   4-ClPh      4-CF.sub.3Ph                    0  H   H   H       H  H1508   4-ClPh      2-FPh     0  H   H   H       H  H1509   4-ClPh      2-ClPh    0  H   H   H       H  H1510   4-ClPh       -n-C.sub.4 F.sub.9                    0  H   H   H       H  H1511   2-ClPh      4-FPh     0  H   H   H       H  H1512   2-ClPh      2,4-Cl.sub.2Ph                    0  H   H   H       H  H1513   2-ClPh      4-ClPh    0  H   H   H       H  H   149-150 Low R.sub.f                                              isomer                                              141-143 High R.sub.f                                              isomer1514   2-ClPh      2,4-F.sub.2Ph                    0  H   H   H       H  H   138-140 Isomer A                                              152-156 Isomer B1515   2-ClPh      4-CF.sub.3Ph                    0  H   H   H       H  H1516   2-ClPh      2-FPh     0  H   H   H       H  H1517   2-ClPh      2-ClPh    0  H   H   H       H  H1518   2-ClPh       -n-C.sub.4 F.sub.9                    0  H   H   H       H  H1519   3-ClPh      4-FPh     0  H   H   H       H  H1520   3-ClPh      2,4-Cl.sub.2Ph                    0  H   H   H       H  H1521   3-ClPh      4-ClPh    0  H   H   H       H  H1522   3-ClPh      2,4-F.sub.2Ph                    0  H   H   H       H  H1523   3-ClPh      4-CF.sub.3Ph                    0  H   H   H       H  H1524   3-ClPh      2-FPh     0  H   H   H       H  H1525   3-ClPh      2-ClPh    0  H   H   H       H  H1526   3-ClPh       -n-C.sub.4 F.sub.9                    0  H   H   H       H  H1527   Ph          4-FPh     0  H   H   H       H  H   88-941528   Ph          2,4-Cl.sub.2Ph                    0  H   H   H       H  H1529   Ph          4-ClPh    0  H   H   H       H  H   156-1581530   Ph          2,4-F.sub.2Ph                    0  H   H   H       H  H   87-90 Low R.sub.f                                              isomer                                              148-150 High R.sub.f                                              isomer1531   Ph          4-CF.sub.3Ph                    0  H   H   H       H  H1532   Ph          2-FPh     0  H   H   H       H  H1533   Ph          2-ClPh    0  H   H   H       H  H1534   Ph           -n-C.sub.4 F.sub.9                    0  H   H   H       H  H1535   4-CF.sub.3Ph          4-FPh     0  H   H   H       H  H1536   4-CF.sub.3Ph          2,4-Cl.sub.2Ph                    0  H   H   H       H  H1537   4-CF.sub.3Ph          4-ClPh    0  H   H   H       H  H1538   4-CF.sub.3Ph          2,4-F.sub.2Ph                    0  H   H   H       H  H1539   4-CF.sub.3Ph          4-CF.sub.3Ph                    0  H   H   H       H  H1540   4-CF.sub.3Ph          2-FPh     0  H   H   H       H  H1541   4-CF.sub.3Ph          2-ClPh    0  H   H   H       H  H1542   4-CF.sub.3Ph           -n-C.sub.4 F.sub.9                    0  H   H   H       H  H1543   4-BrPh      4-FPh     0  H   H   H       H  H1544   4-BrPh      2,4-Cl.sub.2Ph                    0  H   H   H       H  H1545   4-BrPh      4-ClPh    0  H   H   H       H  H1546   4-BrPh      2,4-F.sub.2Ph                    0  H   H   H       H  H1547   4-BrPh      4-CF.sub.3Ph                    0  H   H   H       H  H1548   4-BrPh      2-FPh     0  H   H   H       H  H1549   4-BrPh      2-ClPh    0  H   H   H       H  H1550   4-BrPh       -n-C.sub.4 F.sub.9                    0  H   H   H       H  H1551   2,4-Cl.sub.2Ph          4-FPh     0  H   H   H       H  H1552   2,4-Cl.sub.2Ph          2,4-Cl.sub.2Ph                    0  H   H   H       H  H1553   2,4-Cl.sub.2Ph          4-ClPh    0  H   H   H       H  H1554   2,4-Cl.sub.2Ph          2,4-F.sub.2Ph                    0  H   H   H       H  H1555   2,4-Cl.sub.2Ph          4-CF.sub.3Ph                    0  H   H   H       H  H1556   2,4-Cl.sub.2Ph          2-FPh     0  H   H   H       H  H1557   2,4-Cl.sub.2Ph          2-ClPh    0  H   H   H       H  H1558   2,4-Cl.sub.2Ph           -n-C.sub.4 F.sub.9                    0  H   H   H       H  H1559   2-FPh       4-FPh     0  H   H   H       H  H1560   2-FPh       2,4-Cl.sub.2Ph                    0  H   H   H       H  H1561   2-FPh       4-ClPh    0  H   H   H       H  H1562   2-FPh       2,4-F.sub.2Ph                    0  H   H   H       H  H1563   2-FPh       4-CF.sub.3Ph                    0  H   H   H       H  H1564   2-FPh       2-FPh     0  H   H   H       H  H1565   2-FPh       2-ClPh    0  H   H   H       H  H1566   2-FPh        -n-C.sub.4 F.sub.9                    0  H   H   H       H  H1567   2,4-F.sub.2Ph          4-FPh     0  H   H   H       H  H1568   2,4-F.sub.2Ph          2,4-Cl.sub.2Ph                    0  H   H   H       H  H1569   2,4-F.sub.2Ph          4-ClPh    0  H   H   H       H  H1570   2,4-F.sub.2Ph          2,4-F.sub.2Ph                    0  H   H   H       H  H1571   2,4-F.sub.2Ph          4-CF.sub.3Ph                    0  H   H   H       H  H1572   2,4-F.sub.2Ph          2-FPh     0  H   H   H       H  H1573   2,4-F.sub.2Ph          2-ClPh    0  H   H   H       H  H1574   2,4-F.sub.2Ph           -n-C.sub.4 F.sub.9                    0  H   H   H       H  H1575   Ph          4-FPh     0  H   CH.sub.3                               H       H  H1576   Ph          4-FPh     0  (CH.sub.2).sub.2                               H       H  H1577   Ph          4-FPh     0  CH.sub.3                           CH.sub.3                               H       H  H1578   4-FPh       4-FPh     0  H   CH.sub.3                               H       H  H1579   4-FPh       4-FPh     0  (CH.sub.2).sub.2                               H       H  H1580   4-FPh       4-FPh     0  CH.sub.3                           CH.sub.3                               H       H  H1581   4-ClPh      2,4-Cl.sub.2Ph                    0  H   CH.sub.3                               H       H  H1582   4-ClPh      2,4-Cl.sub.2Ph                    0  (CH.sub.2).sub.2                               H       H  H1583   4-ClPh      2,4-Cl.sub.2Ph                    0  CH.sub.3                           CH.sub.3                               H       H  H1584   2-ClPh      4-ClPh    0  H   CH.sub.3                               H       H  H1585   2-ClPh      4-ClPh    0  (CH.sub.2).sub.2                               H       H  H1586   2-ClPh      4-ClPh    0  CH.sub.3                           CH.sub.3                               H       H  H1587   4-FPh       4-FPh     0  H   C.sub.2 H.sub.5                               H       H  H1588   4-FPh       4-FPh     0  H    .sub.-i-C.sub.3 H.sub.7                               H       H  H1589   4-FPh       4-FPh     0  H    -n-C.sub.4 H.sub.9                               H       H  H1590   4-FPh       4-FPh     0  H   Ph  H       H  H1591   4-FPh       4-FPh     0  H    .sub.-t-C.sub.4 H.sub.9                               H       H  H1592   4-FPh       4-FPh     0  H   Ph  H       H  H1593   4-FPh       4-FPh     0  CH.sub.3                            .sub.-t-C.sub.4 H.sub.9                               H       H  H1594   4-FPh       4-FPh     0  CH.sub.3                           Ph  H       H  H1595   4-FPh       4-FPh     0  (CH.sub.2).sub.3                               H       H  H1596   4-FPh       4-FPh     0  (CH.sub.2).sub.4                               H       H  H1597   4-FPh       4-FPh     0  (CH.sub.2).sub.5                               H       H  H1598   4-FPh       4-FPh     0  (CH.sub.2).sub.6                               H       H  H1599   4-CH.sub.3Ph          4-FPh     0  H   CH.sub.3                               H       H  H1600   4-FPh       4-FPh     1  H   CH.sub.3                               H       H  H1601   4-ClPh      4-FPh     4  H   CH.sub.3                               H       H  H1602    -n-C.sub.4 F.sub.9          4-FPh     0  H   CH.sub.3                               H       H  H1603   (CH.sub.3).sub.2 N          4-FPh     1  H   CH.sub.3                               H       H  H1604   5-Cl-2-thienyl          4-FPh     0  H   CH.sub.3                               H       H  H1605   2-Cl-3-thienyl          4-FPh     0  H   CH.sub.3                               H       H  H1606   1-imidazoyl 4-FPh     0  H   CH.sub.3                               H       H  H1607   4-FPh       4-FPh     0  H   H   CH.sub. 3                                       H  H1608   4-FPh       4-FPh     0  H   H   CH.sub.2 CHCH.sub.2                                       H  H1609   4-FPh       4-FPh     0  H   H   COCH.sub.3                                       H  H1610   4-FPh       4-FPh     0  H   H   CO.sub.2 CH.sub.3                                       H  H1611   4-CF.sub.3 OPh          4-FPh     0  H   H   H       H  H1612   2-ClPh      4-ClPh    0  H   H   CH.sub.3                                       H  H1613   2-ClPh      4-ClPh    0  H   H   CH.sub.2 CHCH.sub.2                                       H  H1614   2-ClPh      4-ClPh    0  H   H   COCH.sub.3                                       H  H1615   2-ClPh      4-ClPh    0  H   H   CO.sub.2 CH.sub.3                                       H  H1616   4-ClPh      2,4-Cl.sub.2Ph                    0  H   H   CH.sub.3                                       H  H1617   4-ClPh      2,4-Cl.sub.2Ph                    0  H   H   CH.sub.2 CHCH.sub.2                                       H  H1618   4-ClPh      2,4-Cl.sub.2Ph                    0  H   H   COCH.sub.3                                       H  H1619   4-ClPh      2,4-Cl.sub.2Ph                    0  H   H   CO.sub.2 CH.sub.3                                       H  H1620   Ph          4-FPh     0  H   H   CH.sub.3                                       H  H1621   Ph          4-FPh     0  H   H   CH.sub.2 CHCH.sub.2                                       H  H1622   Ph          4-FPh     0  H   H   COCH.sub. 3                                       H  H1623   Ph          4-FPh     0  H   H   CO.sub.2 CH.sub.3                                       H  H1624   OH          2,4-Cl.sub.2Ph                    2  H   H   H       H  H1625   OH          2,4-Cl.sub.2Ph                    3  H   H   H       H  H1626   OH          2,4-Cl.sub.2Ph                    4  H   H   H       H  H1627   1-imidazoyl 2,4-Cl.sub.2Ph                    1  H   H   H       H  H1628   1-imidazoyl 2,4-Cl.sub.2Ph                    2  H   H   H       H  H1629   1-imidazoyl 4-FPh     3  H   H   H       H  H1630   1-imidazoyl 4-FPh     4  H   H   H       H  H1631   1H-1,2,4-triazoyl-1-yl          4-FPh     1  H   H   H       H  H1632   1H-1,2,4-triazoyl-1-yl          4-FPh     2  H   H   H       H  H1633   1H-1,2,4-triazoyl-1-yl          4-FPh     3  H   H   H       H  H1634   1H-1,2,4-triazoyl-1-yl          4-FPh     4  H   H   H       H  H1635   1H-1,2,4-triazoyl-1-yl          2,4-Cl.sub.2Ph                    1  H   H   H       H  H1636   Ph          2,5-F.sub.2Ph                    0  H   H   H       H  H1637   Ph          3-FPh     0  H   H   H       H  H1638   Ph          2,5-Cl.sub.2Ph                    0  H   H   H       H  H1639   Ph          3-ClPh    0  H   H   H       H  H1640   Ph          4-BrPh    0  H   H   H       H  H1641   Ph          4-IPh     0  H   H   H       H  H1642   Ph          3,4-F.sub.2Ph                    0  H   H   H       H  H1643   Ph          3,4-Cl.sub.2Ph                    0  H   H   H       H  H1644   Ph          2,6-Cl.sub.2Ph                    0  H   H   H       H  H1645   Ph          2-Cl(4-F)Ph                    0  H   H   H       H  H1646   Ph          2,4,6-Cl.sub.3Ph                    0  H   H   H       H  H1647   Ph          2-F(4-Cl)Ph                    0  H   H   H       H  H1648   Ph          Ph        0  H   H   H       H  H1649   Ph          4-CH.sub.3Ph                    0  H   H   H       H  H1650   Ph          3-CH.sub.3Ph                    0  H   H   H       H  H1651   Ph          2-CH.sub.3Ph                    0  H   H   H       H  H1652   Ph          2-CF.sub.3Ph                    0  H   H   H       H  H1653   Ph          3-CF.sub.3Ph                    0  H   H   H       H  H1654   Ph          2-F(4-CF.sub.3)Ph                    0  H   H   H       H  H1655   Ph          4-CH.sub.3 OPh                    0  H   H   H       H  H1656   Ph          5-Cl-2-pyridyl                    0  H   H   H       H  H1657   Ph          5-Cl-2-thienyl                    0  H   H   H       H  H1658   Ph          2-Cl-3-thienyl                    0  H   H   H       H  H1659   Ph           .sub.-s-C.sub.4 H.sub.9                    0  H   H   H       H  H1660   2-ClPh      2,5-F.sub.2Ph                    0  H   H   H       H  H1661   2-ClPh      3-FPh     0  H   H   H       H  H1662   2-ClPh      2,5-Cl.sub.2Ph                    0  H   H   H       H  H1663   2-ClPh      3-ClPh    0  H   H   H       H  H1664   2-ClPh      4-BrPh    0  H   H   H       H  H1665   2-ClPh      4-IPh     0  H   H   H       H  H1666   2-ClPh      3,4-F.sub.2Ph                    0  H   H   H       H  H1667   2-ClPh      3,4-Cl.sub.2Ph                    0  H   H   H       H  H1668   2-ClPh      2,6-Cl.sub.2Ph                    0  H   H   H       H  H1669   2-ClPh      2-Cl(4-F)Ph                    0  H   H   H       H  H1670   2-ClPh      2,4,6-Cl.sub.3Ph                    0  H   H   H       H  H1671   2-ClPh      2-F(4-Cl)Ph                    0  H   H   H       H  H1672   2-ClPh      Ph        0  H   H   H       H  H1673   2-ClPh      4-CH.sub.3Ph                    0  H   H   H       H  H1674   2-ClPh      3-CH.sub.3Ph                    0  H   H   H       H  H1675   2-ClPh      2-CH.sub.3Ph                    0  H   H   H       H  H1676   2-ClPh      2-CF.sub.3Ph                    0  H   H   H       H  H1677   2-ClPh      3-CF.sub. 3Ph                    0  H   H   H       H  H1678   2-ClPh      2-F(4-CF.sub.3)Ph                    0  H   H   H       H  H1679   2-ClPh      4-CH.sub.3 OPh                    0  H   H   H       H  H1680   2-ClPh      5-Cl-2-pyridyl                    0  H   H   H       H  H1681   2-ClPh      5-Cl-2-thienyl                    0  H   H   H       H  H1682   2-ClPh      2-Cl-3-thienyl                    0  H   H   H       H  H1683   3-ClPh      2,5-F.sub.2Ph                    0  H   H   H       H  H1684   3-ClPh      2,5-Cl.sub.2Ph                    0  H   H   H       H  H1685   4-FPh       2,5-F.sub.2Ph                    0  H   H   H       H  H1686   4-FPh       3-FPh     0  H   H   H       H  H1687   4-FPh       2,5-Cl.sub.2Ph                    0  H   H   H       H  H1688   4-FPh       3-ClPh    0  H   H   H       H  H1689   4-FPh       4-BrPh    0  H   H   H       H  H1690   4-FPh       4-IPh     0  H   H   H       H  H1691   4-FPh       3,4-F.sub.2Ph                    0  H   H   H       H  H1692   4-FPh       3,4-Cl.sub.2Ph                    0  H   H   H       H  H1693   4-FPh       2,6-Cl.sub.2Ph                    0  H   H   H       H  H1694   4-FPh       2-Cl(4-F)Ph                    0  H   H   H       H  H1695   4-FPh       2,4,6-Cl.sub.3Ph                    0  H   H   H       H  H1696   4-FPh       2-F(4-Cl)Ph                    0  H   H   H       H  H1697   4-FPh       Ph        0  H   H   H       H  H1698   4-FPh       4-CH.sub.3Ph                    0  H   H   H       H  H1699   4-FPh       3-CH.sub.3Ph                    0  H   H   H       H  H1700   4-FPh       2-CH.sub.3Ph                    0  H   H   H       H  H1701   4-FPh       2-CF.sub.3Ph                    0  H   H   H       H  H1702   4-FPh       3-CF.sub.3Ph                    0  H   H   H       H  H1703   4-FPh       2-F(4-CF.sub.3)Ph                    0  H   H   H       H  H1704   4-FPh       4-CH.sub.3 OPh                    0  H   H   H       H  H1705   4-FPh       5-Cl-2-pyridyl                    0  H   H   H       H  H1706   4-FPh       2-Cl-3-thienyl                    0  H   H   H       H  H1707   4-FPh       5-Cl-2-thienyl                    0  H   H   H       H  H1708   3-FPh       2,5-Cl.sub.2Ph                    0  H   H   H       H  H1709   3-FPh       2,5-F.sub.2Ph                    0  H   H   H       H  H1710   4-ClPh      2,5-F.sub.2Ph                    0  H   H   H       H  H1711   4-ClPh      3-FPh     0  H   H   H       H  H1712   4-ClPh      2,5-Cl.sub.2Ph                    0  H   H   H       H  H1713   4-ClPh      3-ClPh    0  H   H   H       H  H1714   4-ClPh      4-BrPh    0  H   H   H       H  H1715   4-ClPh      4-IPh     0  H   H   H       H  H1716   4-ClPh      3,4-F.sub.2Ph                    0  H   H   H       H  H1717   4-ClPh      3,4-Cl.sub.2Ph                    0  H   H   H       H  H1718   4-ClPh      2,6-Cl.sub.2Ph                    0  H   H   H       H  H1719   4-ClPh      2-Cl(4-F)Ph                    0  H   H   H       H  H1720   4-ClPh      2,4,6-Cl.sub.3Ph                    0  H   H   H       H  H1721   4-ClPh      2-F(4-Cl)Ph                    0  H   H   H       H  H1722   4-ClPh      Ph        0  H   H   H       H  H1723   4-ClPh      4-CH.sub.3Ph                    0  H   H   H       H  H1724   4-ClPh      3-CH.sub.3Ph                    0  H   H   H       H  H1725   4-ClPh      2-CH.sub.3Ph                    0  H   H   H       H  H1726   4-ClPh      2-CF.sub.3Ph                    0  H   H   H       H  H1727   4-ClPh      3-CF.sub.3Ph                    0  H   H   H       H  H1728   4-ClPh      2-F(4-CF.sub.3)Ph                    0  H   H   H       H  H1729   4-ClPh      4-CH.sub.3 OPh                    0  H   H   H       H  H1730   4-ClPh      5-Cl-2-pyridyl                    0  H   H   H       H  H1731   4-ClPh      5-Cl-2-thienyl                    0  H   H   H       H  H1732   4-ClPh      2-Cl-3-thienyl                    0  H   H   H       H  H1733   4-ClPh           ##STR69##                    0  H   H   H       H  H1734   4-ClPh       .sub.-t-butyl                    0  H   H   H       H  H1735   4-ClPh       -n-hexyl 0  H   H   H       H  H1736   4-ClPh       -n-heptyl                    0  H   H   H       H  H1737   4-ClPh       -n-octyl 0  H   H   H       H  H1738   4-ClPh      C.sub.6 F.sub.13                    0  H   H   H       H  H1739   4-ClPh      C.sub.8 F.sub.17                    0  H   H   H       H  H1740   4-ClPh      4-pyridyl 0  H   H   H       H  H1741   4-ClPh      2-pyridyl 0  H   H   H       H  H1742   4-ClPh      2-thienyl 0  H   H   H       H  H1743   4-ClPh      4- -n-BuPh                    0  H   H   H       H  H1744   4-ClPh      4-  -n-BuOPh                    0  H   H   H       H  H1745   4-ClPh      5-CF.sub.3 -2-pyridyl                    0  H   H   H       H  H1746   4-ClPh      5-CH.sub.3 SO.sub.2 -2-                    0  H   H   H       H  H          thienyl1747   4-C.sub.2 H.sub.5Ph          4-FPh     0  H   H   H       H  H1748   4-( -n-BuO)Ph          4-FPh     0  H   H   H       H  H1749   2-CH.sub.3 SO.sub.2 -imida-          4-FPh     0  H   H   H       H  H   zol-1-yl1750   5-CH.sub.3 S-1,2,4-          4-FPh     0  H   H   H       H  H   triazol-1-yl1751   C.sub.6 F.sub.13          4-FPh     0  H   H   H       H  H1752   C.sub.8 F.sub.17          4-FPh     0  H   H   H       H  H1753   3-CH.sub.3 OPh          4-FPh     0  H   H   H       H  H1754   2-CF.sub.3 -imidazol-1-yl          4-FPh     0  H   H   H       H  H1755   4-( .sub.-i-C.sub.3 H.sub.7 O)Ph          4-FPh     0  H   H   H       H  H1756   4-IPh       4-FPh     0  H   H   H       H  H1757   3,4-F.sub.2Ph          4-FPh     0  H   H   H       H  H1758   3,4-Cl.sub.2Ph          4-F Ph    0  H   H   H       H  H1759   2,6-Cl.sub.2Ph          4-FPh     0  H   H   H       H  H1760   2-Cl(4-F)Ph 4-FPh     0  H   H   H       H  H1761   2,4,6-Cl.sub.3Ph          4-FPh     0  H   H   H       H  H1762   4-CH.sub.3Ph          4-FPh     0  H   H   H       H  H1763   3-CH.sub.3Ph          4-FPh     0  H   H   H       H  H1764   2-CH.sub.3Ph          4-FPh     0  H   H   H       H  H1765   2-CF.sub.3Ph          4-FPh     0  H   H   H       H  H1766   3-CF.sub.3Ph          4-FPh     0  H   H   H       H  H1767   4-CH.sub.3 OPh          4-FPh     0  H   H   H       H  H1768   2,3-Cl.sub.2Ph          4-FPh     0  H   H   H       H  H1769   3,5-Cl.sub.2Ph          4-FPh     0  H   H   H       H  H1770   2,5-Cl.sub.2Ph          4-FPh     0  H   H   H       H  H1771   3-BrPh      4-FPh     0  H   H   H       H  H1772   4-C.sub.2 H.sub.5 OPh          4-FPh     0  H   H   H       H  H1773   2,4-(CH.sub.3).sub.2Ph          4-FPh     0  H   H   H       H  H1774   2,4,6-(CH.sub.3).sub.3Ph          4-FPh     0  H   H   H       H  H1775   4-PhPh      4-FPh     0  H   H   H       H  H1776   5-Cl-2-thienyl          4-FPh     0  H   H   H       H  H1777   2-Cl-3-thienyl          4-FPh     0  H   H   H       H  H1778   1-imidazoyl 4-FPh     0  H   H   H       H  H1779   1H-1,2,4-triazoyl-1-yl          4-FPh     0  H   H   H       H  H1780   2-pyridyl   4-FPh     0  H   H   H       H  H1781   5-Cl-2-pyridyl          4-FPh     0  H   H   H       H  H1782   3-pyridyl   4-FPh     0  H   H   H       H  H1783   4-pyridyl   4-FPh     0  H   H   H       H  H1784    -n-C.sub.4 F.sub.9          4-FPh     0  H   H   H       H  H1785   4-IPh       2,4-Cl.sub.2Ph                    0  H   H   H       H  H1786   3,4-F.sub.2Ph          2,4-Cl.sub.2Ph                    0  H   H   H       H  H1787   3,4-Cl.sub.2Ph          2,4-Cl.sub.2Ph                    0  H   H   H       H  H1788   2,6-Cl.sub.2Ph          2,4-Cl.sub.2Ph                    0  H   H   H       H  H1789   2-Cl(4-F)Ph 2,4-Cl.sub.2Ph                    0  H   H   H       H  H1790   2,4,6-Cl.sub.3Ph          2,4-Cl.sub.2Ph                    0  H   H   H       H  H1791   4-CH.sub.3Ph          2,4-Cl.sub.2Ph                    0  H   H   H       H  H1792   3-CH.sub.3Ph          2,4-Cl.sub.2Ph                    0  H   H   H       H  H1793   2-CH.sub.3Ph          2,4-Cl.sub.2Ph                    0  H   H   H       H  H1794   2-CF.sub.3Ph          2,4-Cl.sub.2Ph                    0  H   H   H       H  H1795   3-CF.sub.3Ph          2,4-Cl.sub.2Ph                    0  H   H   H       H  H1796   4-CH.sub.3 OPh          2,4-Cl.sub.2Ph                    0  H   H   H       H  H1797   2,3-Cl.sub.2Ph          2,4-Cl.sub.2Ph                    0  H   H   H       H  H1798   3,5-Cl.sub.2Ph          2,4-Cl.sub.2Ph                    0  H   H   H       H  H1799   2,5-Cl.sub.2Ph          2,4-Cl.sub.2Ph                    0  H   H   H       H  H1800   3-BrPh      2,4-Cl.sub.2Ph                    0  H   H   H       H  H1801   4-C.sub.2 H.sub.5 OPh          2,4-Cl.sub.2Ph                    0  H   H   H       H  H1802   2,4-(CH.sub.3).sub.2Ph          2,4-Cl.sub.2Ph                    0  H   H   H       H  H1803   2,4,6-(CH.sub.3).sub.3Ph          2,4-Cl.sub.2Ph                    0  H   H   H       H  H1804   4-PhPh      2,4-Cl.sub.2Ph                    0  H   H   H       H  H1805   5-Cl-2-thienyl          2,4-Cl.sub.2Ph                    0  H   H   H       H  H1806   2-Cl-3-thienyl          2,4-Cl.sub.2Ph                    0  H   H   H       H  H1807   1-imidazoyl 2,4-Cl.sub.2Ph                    0  H   H   H       H  H1808   1H-1,2,4-triazoyl-1-yl          2,4-Cl.sub.2Ph                    0  H   H   H       H  H1809   2-pyridyl   2,4-Cl.sub.2Ph                    0  H   H   H       H  H1810   5-Cl-2-pyridyl          2,4-Cl.sub.2Ph                    0  H   H   H       H  H1811   3-pyridyl   2,4-Cl.sub.2Ph                    0  H   H   H       H  H1812   4-pyridyl   2,4-Cl.sub.2Ph                    0  H   H   H       H  H1813    -n-C.sub.4 F.sub.9          2,4-Cl.sub.2Ph                    0  H   H   H       H  H1814   4-IPh       4-ClPh    0  H   H   H       H  H1815   3,4-F.sub.2Ph          4-ClPh    0  H   H   H       H  H1816   3,4-Cl.sub.2Ph          4-ClPh    0  H   H   H       H  H1817   2,6-Cl.sub.2Ph          4-ClPh    0  H   H   H       H  H1818   2-Cl(4-F)Ph 4-ClPh    0  H   H   H       H  H1819   2,4,6-Cl.sub.3Ph          4-ClPh    0  H   H   H       H  H1820   4-CH.sub.3Ph          4-ClPh    0  H   H   H       H  H1821   3-CH.sub.3Ph          4-ClPh    0  H   H   H       H  H1822   2-CH.sub.3Ph          4-ClPh    0  H   H   H       H  H1823   2-CF.sub.3Ph          4-ClPh    0  H   H   H       H  H1824   3-CF.sub.3Ph          4-ClPh    0  H   H   H       H  H1825   4-CH.sub.3 OPh          4-ClPh    0  H   H   H       H  H1826   2,3-Cl.sub.2Ph          4-ClPh    0  H   H   H       H  H1827   3,5-Cl.sub.2Ph          4-ClPh    0  H   H   H       H  H1828   2,5-Cl.sub.2Ph          4-ClPh    0  H   H   H       H  H1829   3-BrPh      4-ClPh    0  H   H   H       H  H1830   4-EtOPh     4-ClPh    0  H   H   H       H  H1831   2,4-(CH.sub.3).sub.2Ph          4-ClPh    0  H   H   H       H  H1832   2,4,6-(CH.sub.3).sub.3Ph          4-ClPh    0  H   H   H       H  H1833   4-PhPh      4-ClPh    0  H   H   H       H  H1834   5-Cl-2-thienyl          4-ClPh    0  H   H   H       H  H1835   2-Cl-3-thienyl          4-ClPh    0  H   H   H       H  H1836   1-imidazoyl 4-ClPh    0  H   H   H       H  H1837   1H-1,2,4-triazoyl-1-yl          4-ClPh    0  H   H   H       H  H1838   2-pyridyl   4-ClPh    0  H   H   H       H  H1839   5-Cl-2-pyridyl          4-ClPh    0  H   H   H       H  H1840   3-pyridyl   4-ClPh    0  H   H   H       H  H1841   4-pyridyl   4-ClPh    0  H   H   H       H  H1842    -n-C.sub.4 F.sub.9          4-ClPh    0  H   H   H       H  H1843   4-IPh       2,4-F.sub.2Ph                    0  H   H   H       H  H1844   3,4-F.sub.2Ph          2,4-F.sub.2Ph                    0  H   H   H       H  H1845   3,4-Cl.sub.2Ph          2,4-F.sub.2Ph                    0  H   H   H       H  H1846   2,6-Cl.sub.2Ph          2,4-F.sub.2Ph                    0  H   H   H       H  H1847   2-Cl(4-F)Ph 2,4-F.sub.2Ph                    0  H   H   H       H  H1848   2,4,6-Cl.sub.3Ph          2,4-F.sub.2Ph                    0  H   H   H       H  H1849   4-CH.sub.3Ph          2,4-F.sub.2Ph                    0  H   H   H       H  H1850   3-CH.sub.3Ph          2,4-F.sub.2Ph                    0  H   H   H       H  H1851   2-CH.sub.3Ph          2,4-F.sub.2Ph                    0  H   H   H       H  H1852   2-CF.sub.3Ph          2,4-F.sub.2Ph                    0  H   H   H       H  H1853   3-CF.sub.3Ph          2,4-F.sub.2Ph                    0  H   H   H       H  H1854   4-CH.sub.3 OPh          2,4-F.sub.2Ph                    0  H   H   H       H  H1855   2,3-Cl.sub.2Ph          2,4-F.sub.2Ph                    0  H   H   H       H  H1856   3,5-Cl.sub.2Ph          2,4-F.sub.2Ph                    0  H   H   H       H  H1857   2,5-Cl.sub.2Ph          2,4-F.sub.2Ph                    0  H   H   H       H  H1858   3-BrPh      2,4-F.sub.2Ph                    0  H   H   H       H  H1859   4-C.sub.2 H.sub.5 OPh          2,4-F.sub.2Ph                    0  H   H   H       H  H1860   2,4-(CH.sub.3).sub.2Ph          2,4-F.sub.2Ph                    0  H   H   H       H  H1861   2,4,6-(CH.sub.3).sub.3Ph          2,4-F.sub.2Ph                    0  H   H   H       H  H1862   4-PhPh      2,4-F.sub.2Ph                    0  H   H   H       H  H1863   5-Cl-2-thienyl          2,4-F.sub.2Ph                    0  H   H   H       H  H1864   2-Cl-3-thienyl          2,4-F.sub.2Ph                    0  H   H   H       H  H1865   1-imidazoyl 2,4-F.sub.2Ph                    0  H   H   H       H  H1866   1H-1,2,4-triazoyl-1-yl          2,4-F.sub.2Ph                    0  H   H   H       H  H1867   2-pyridyl   2,4-F.sub.2Ph                    0  H   H   H       H  H1868   5-Cl-2-pyridyl          2,4-F.sub.2Ph                    0  H   H   H       H  H1869   3-pyridyl   2,4-F.sub.2Ph                    0  H   H   H       H  H1870   4-pyridyl   2,4-F.sub.2Ph                    0  H   H   H       H  H1871    -n-C.sub.4 F.sub.9          2,4-F.sub.2Ph                    0  H   H   H       H  H1872   4-FPh       4-FPh     0  H   H   H       CH.sub. 3                                          H1873   4-FPh       4-FPh     0  H   H   H       CH.sub.3                                          CH.sub.31874   4-FPh       4-FPh     0  H   H   H       F  H1875   4-FPh       4-FPh     0  H   H   H       F  CH.sub.31876   4-FPh       4-FPh     0  H   H   H       F  F1877   4-ClPh      2,4-Cl.sub.2Ph                    0  H   H   H       CH.sub.3                                          H1878   4-ClPh      2,4-Cl.sub.2Ph                    0  H   H   H       CH.sub.3                                          CH.sub.31879   4-ClPh      2,4-Cl.sub.2Ph                    0  H   H   H       F  H1880   4-ClPh      2,4-Cl.sub.2Ph                    0  H   H   H       F  CH.sub.31881   4-ClPh      2,4-Cl.sub.2Ph                    0  H   H   H       F  F1882   2-ClPh      4-ClPh    0  H   H   H       CH.sub.3                                          H1883   2-ClPh      4-ClPh    0  H   H   H       CH.sub.3                                          CH.sub.31884   2-ClPh      4-ClPh    0  H   H   H       F  H1885   2-ClPh      4-ClPh    0  H   H   H       F  CH.sub.31886   2-ClPh      4-ClPh    0  H   H   H       F  F1887   Ph          4-FPh     0  H   H   H       CH.sub.3                                          H1888   Ph          4-FPh     0  H   H   H       CH.sub.3                                          CH.sub.31889   Ph          4-FPh     0  H   H   H       F  H1890   Ph          4-FPh     0  H   H   H       F  CH.sub.31891   Ph          4-FPh     0  H   H   H       F  F__________________________________________________________________________ .sup.a NMR: (CDCl.sub.3) δ 2.7 (m, 2H), 4.4 (1/2 of ABq, J = 12, 1H), 4.9 (1/2 of ABq, J = 12, 1H), 5.0 (br s, 1H, 0H), 6.7 (m, 2H), 7.0 (m, 2H), 7.4 (m, 3H), 7.8 (s, 1H), 8.0 (s, 1H). 
    
     EXAMPLE 1930 
     2-(2,4-Difluorophenyl)-3-(2-chlorophenyl)-1-(1H-1,2,4-imidazol-1-yl)-3-buten-2-ol 
     A mixture of 10.2 g (0.035 mol) of 2-(2,4-difluorophenyl)-2-[1-(2-chlorophenyl)ethenyl]oxirane; 6.20 g (0.091 mol) of imidazole and 12.44 g (0.091 mol) of potassium carbonate in 100 mL of DMSO was heated overnight at 100°, then cooled and poured into 800 mL of H 2  O. The aqueous mixture was extracted with 4×500 mL Et 2  O, and the organic extracts were washed with water (2×) and brine, dried over MgSO 4  and evaporated to give 7.8 g of a yellow-brown solid. Flash chromatography and trituration with Et 2  O gave 4.0 g of a white powder, mp 139°-142°: NMR: (CDCl 3 ) δ3.9 (br, OH), 4.2 (1/2 of ABq, 1H), 4.7 (1/2 of ABq, 1H, CH 2  -imidazole), 5.3 (s, 1H, vinyl), 5.5 (s, 1H, vinyl), 6.7 (m, 4 H), 7.0-7.5 (m, 6H); IR (nujol) 3400-2600 (br), 1614, 1512, 1501, 1111, 1075, 852, 819, 768, 743, 623 cm -1 . 
     The compounds shown in Table 4A were prepared or can be prepared by the methods described above. 
     
                                           TABLE 4A__________________________________________________________________________ ##STR70##Ex.No.   A      B       n R  R.sup.1                     R.sup.2                        R.sup.3                           R.sup.4                             M.P. °C.__________________________________________________________________________1892   Ph     Ph      0 H  H  H  H1893   Ph     2-FPh   0 H  H  H  H1894   Ph     4-FPh   0 H  H  H  H    (oil).sup.a1895   Ph     2,4-F.sub.2Ph             0 H  H  H  H    157-1581896   Ph     2-ClPh  0 H  H  H  H1897   Ph     4-ClPh  0 H  H  H  H1898   Ph     2,4-Cl.sub.2Ph             0 H  H  H  H1899   2-FPh  Ph      0 H  H  H  H1900   2-FPh  2-FPh   0 H  H  H  H1901   2-FPh  4-FPh   0 H  H  H  H1902   2-FPh  2,4-F.sub.2Ph             0 H  H  H  H1903   2-FPh  2-ClPh  0 H  H  H  H1904   2-FPh  4-ClPh  0 H  H  H  H1905   2-FPh  2,4-Cl.sub.2Ph             0 H  H  H  H1906   3-FPh  Ph      0 H  H  H  H1907   3-FPh  2-FPh   0 H  H  H  H1908   3-FPh  4-FPh   0 H  H  H  H1909   3-FPh  2,4-F.sub.2Ph             0 H  H  H  H1910   3-FPh  2-ClPh  0 H  H  H  H1911   3-FPh  4-ClPh  0 H  H  H  H1912   3-FPh  2,4-Cl.sub.2Ph             0 H  H  H  H1913   4-FPh  Ph      0 H  H  H  H1914   4-FPh  2-FPh   0 H  H  H  H    159-1601915   4-FPh  4-FPh   0 H  H  H  H    175-1771916   4-FPh  2,4-F.sub.2Ph             0 H  H  H  H    194-1971917   4-FPh  2-ClPh  0 H  H  H  H1918   4-FPh  4-ClPh  0 H  H  H  H1919   4-FPh  2,4-Cl.sub.2Ph             0 H  H  H  H    200-215 (60%                             pure)1920   2,4-F.sub.2Ph     Ph      0 H  H  H  H1921   2,4-F.sub.2Ph     2-FPh   0 H  H  H  H1922   2,4-F.sub.2Ph     4-FPh   0 H  H  H  H1923   2,4-F.sub.2Ph     2,4-F.sub.2Ph             0 H  H  H  H1924   2,4-F.sub.2Ph     2-ClPh  0 H  H  H  H1925   2,4-F.sub.2Ph     4-ClPh  0 H  H  H  H1926   2,4-F.sub.2Ph     2,4-Cl.sub.2Ph             0 H  H  H  H1927   2-ClPh Ph      0 H  H  H  H1928   2-ClPh 2-FPh   0 H  H  H  H1929   2-ClPh 4-FPh   0 H  H  H  H1930   2-ClPh 2,4-F.sub.2Ph             0 H  H  H  H    139-142                             (HCl salt                             215-217)1931   2-ClPh 2-ClPh  0 H  H  H  H1932   2-ClPh 4-ClPh  0 H  H  H  H    160-162                             (HCl salt                             170-173)1933   2-ClPh 2,4-Cl.sub.2 Ph             0 H  H  H  H1934   3-ClPh Ph      0 H  H  H  H  H1935   3-ClPh 2-FPh   0 H  H  H  H  H1936   3-ClPh 4-FPh   0 H  H  H  H  H1937   3-ClPh 2,4-F.sub.2Ph             0 H  H  H  H  H1938   3-ClPh 2-ClPh  0 H  H  H  H  H1939   3-ClPh 4-ClPh  0 H  H  H  H  H1940   3-ClPh 2,4-Cl.sub.2Ph             0 H  H  H  H  H1941   4-ClPh Ph      0 H  H  H  H  H1942   4-ClPh 2-FPh   0 H  H  H  H  H1943   4-ClPh 4-FPh   0 H  H  H  H  H1944   4-ClPh 2,4-F.sub.2Ph             0 H  H  H  H  H1945   4-ClPh 2-ClPh  0 H  H  H  H  H1946   4-ClPh 4-ClPh  0 H  H  H  H  H 179-1811947   4-ClPh 2,4-Cl.sub.2Ph             0 H  H  H  H  H1948   2,4-Cl.sub.2Ph     Ph      0 H  H  H  H  H1949   2,4-Cl.sub.2Ph     2-FPh   0 H  H  H  H  H1950   2,4-Cl.sub.2Ph     4-FPh   0 H  H  H  H  H1951   2,4-Cl.sub.2Ph     2,4-F.sub.2Ph             0 H  H  H  H  H1952   2,4-Cl.sub.2Ph     2-ClPh  0 H  H  H  H  H1953   2,4-Cl.sub.2Ph     4-ClPh  0 H  H  H  H  H1954   2,4-Cl.sub.2Ph     2,4-Cl.sub.2Ph             0 H  H  H  H  H1955   2-BrPh Ph      0 H  H  H  H  H1956   2-BrPh 2-FPh   0 H  H  H  H  H1957   2-BrPh 4-FPh   0 H  H  H  H  H1958   2-BrPh 2,4-F.sub.2Ph             0 H  H  H  H  H1959   2-BrPh 2-ClPh  0 H  H  H  H  H1960   2-BrPh 4-ClPh  0 H  H  H  H  H1961   2-BrPh 2,4-Cl.sub.2Ph             0 H  H  H  H  H1962   3-BrPh Ph      0 H  H  H  H  H1963   3-BrPh 2-FPh   0 H  H  H  H  H1964   3-BrPh 4-FPh   0 H  H  H  H  H1965   3-BrPh 2,4-F.sub.2Ph             0 H  H  H  H  H1966   3-BrPh 2-ClPh  0 H  H  H  H  H1967   3-BrPh 4-ClPh  0 H  H  H  H  H1968   3-BrPh 2,4-Cl.sub.2Ph             0 H  H  H  H  H1969   4-BrPh Ph      0 H  H  H  H  H1970   4-BrPh 2-FPh   0 H  H  H  H  H1971   4-BrPh 4-FPh   0 H  H  H  H  H1972   4-BrPh 2,4-F.sub.2Ph             0 H  H  H  H  H1973   4-BrPh 2-ClPh  0 H  H  H  H  H1974   4-BrPh 4-ClPh  0 H  H  H  H  H1975   4-BrPh 2,4-Cl.sub.2Ph             0 H  H  H  H  H1976   2-CF.sub.3Ph     Ph      0 H  H  H  H  H 177-1791977   2-CF.sub.3Ph     2-FPh   0 H  H  H  H  H 185-1871978   2-CF.sub.3Ph     4-FPh   0 H  H  H  H  H 170-1721979   2-CF.sub.3Ph     2,4-F.sub.2Ph             0 H  H  H  H  H1980   2-CF.sub.3Ph     2-ClPh  0 H  H  H  H  H1981   2-CF.sub.3Ph     4-ClPh  0 H  H  H  H  H 159-1611982   2-CF.sub.3Ph     2,4-Cl.sub.2Ph             0 H  H  H  H  H1983   3-CF.sub.3Ph     Ph      0 H  H  H  H  H1984   3-CF.sub.3Ph     2-FPh   0 H  H  H  H  H1985   3-CF.sub.3Ph     4-FPh   0 H  H  H  H  H1986   3-CF.sub.3Ph     2,4-F.sub.2Ph             0 H  H  H  H  H1987   3-CF.sub.3Ph     2-ClPh  0 H  H  H  H  H1988   3-CF.sub.3Ph     4-ClPh  0 H  H  H  H  H1989   3-CF.sub.3Ph     2,4-Cl.sub.2Ph             0 H  H  H  H  H1990   4-CF.sub.3Ph     Ph      0 H  H  H  H  H1991   4-CF.sub.3Ph     2-FPh   0 H  H  H  H  H1992   4-CF.sub.3Ph     4-FPh   0 H  H  H  H  H1993   4-CF.sub.3Ph     2,4-F.sub.2Ph             0 H  H  H  H  H1994   4-CF.sub.3Ph     2-ClPh  0 H  H  H  H  H1995   4-CF.sub.3Ph     4-ClPh  0 H  H  H  H  H1996   4-CF.sub.3Ph     2,4-Cl.sub.2Ph             0 H  H  H  H  H__________________________________________________________________________ 
    
     Pharmaceutical Utility 
     In vitro activity (Table 5) is expressed in terms of the minimal inhibitory concentration (MIC) of the test compound which inhibits the growth of yeasts and fungi. 
     The target organisms, Candida albicans ATCC 11651 and Aspergillus fumigatus ATCC 28214 are standardized, [V. Bezjek, J. Clinical Micro., 21 509-512 (1984)] to a concentration of 10 7  organisms/ml maintained at -70° until use. Test compounds are solubilized in dimethyl sulfoxide (DMSO) and diluted in Eagle&#39;s Minimum Essential Medium (EMEM) broth to achieve a final concentration of 200 μg/ml. Stock solutions of standard antifungal agents are stored at -71° and diluted in EMEM as required. 
     The in vitro assay utilizes a microtiter broth dilution technique [L. Polonelli and G. Morace, Mycopathologia, 86, 21-28 (1984)]and C. Hughes, et al. Antimicrob. Ag. and Chemo., 25, 560-562(1984)]. Test compounds are serially diluted in EMEM to give graded concentrations ranging from 100 to 0.4 μg/ml. The appropriate wells are inoculated with the required organism (C. albicans at 1×10 4  organisms/ml and A. fumigatus at 5×10 5  organism/ml) and the assay incubated at 30° for 24 hours. The extent of fungal growth is determined at an optical density equal to 540 nm using a scanning spectrophotometer (Flow® MCC) and MIC values, representing the minimal concentration of a compound which inhibited growth, are determined, [V. Grenta, et al. Antimicrob. Ag. and Chemo., 22, 151-153 (1982)]. 
     The in vivo activity of test compounds is based on the percent (%) survival of infected animals receiving test or standard agent compared to that in an infected untreated group (Table 6). The in vivo assays are chronic systemic infections lethal to mice within 7 days post infection, [J. Barnes, et al. Lab Investigation, 49 460-467 (1963), and T. Rogers and E. Balish, Infection and Immunity, 14 33-38 (1976)]. 
     Candida albicans ATCC 11651, from a frozen stock culture (10 9  organisms/ml) maintained at -70°, is diluted in saline to 1×10 7  organisms/ml and 0.2 ml inoculated intravenously (caudal vein) into 20.0 gm CF-1 female mice (Charles River). 
     Test compounds are routinely solubilized in 0.25% (w/v) methylcellulose (Methocel®) but for those compounds difficult to solubilize 10% (w/v) Emulophor® (EL620 GAF Corp.) is used. The standard antifungal agents, amphotericin B (Fungizone®) in water and ketoconazole (Nizoral®) in Methocel®, are administered at 1.0 mg/kg/day and 150 mg/kg/day, respectively. 
     In a primary assay, mice (10 per group) are infected with C. albicans, and receive test compounds at 50 or 150 mg/kg/day via the subcutaneous route. Animals are dosed with the test compound at 1 and 6 post-infection and then once daily for the next three days. Survival of mice in each group is recorded for 21 days. 
     Compounds which protect ≧70% of the infected animals for 14 days at a dose 150 mg/kg/day or less are viewed as active. 
     
                       TABLE 5______________________________________In Vitro Antifungal Results ##STR71##Example        MIC values (μg/ml)Number         C. albicans                     A. fumigatus______________________________________1                  ≦0.01                         6.31       HCl salt   0.05       12.52                  ≦0.4                         1.63                  ≦0.4                         504                  0.03       0.86                  1.6        2510                 1.6        2515                 0.1        5016                 0.03       6.317                 0.03       12.525                 1.6        2526                 ≦0.4                         12.526      HCl salt   0.03       0.427                 ≦0.4                         12.528                 0.03       1.632                 ≦0.4                         1.633                 0.03       0.0334                 0.03       3.234      HCl salt   0.03       1.635                 0.03       0.135      HCl salt   0.03       ≦0.239                 0.4        2540                 0.4        3.241                 0.4        5042                 0.03       6.347                 0.03       1.649                 0.03       12.550                 0.1        0.851                 0.03       3.252                 0.03       0.452      HCl salt   0.03       0.465                 0.2        10067                 0.03       10085                 ≦0.4                         12.594                 0.4        5099                 0.05       6.3100                0.03       3.2101                0.03       12.5114                0.4        50117                0.4        100163                0.03       12.5164                0.03       1.6170                1.6        100177                3.2        &gt;100208                1.6        50286                0.4        25291                0.2        100359                0.4        50360                0.8        100361                0.8        25363                100        100447                3.2        N.T.449                ≦0.4                         N.T.450                &gt;100       N.T.451                12.5       N.T.452                &gt;100       N.T.453                1.6        &gt;100454                100        &gt;100455                25         N.T.477                &gt;100       N.T.594                0.8        0.8594     HCl salt   0.03       0.4596                0.05       0.4603                0.1        &gt;100605                0.2        100608                0.4        6.3620                0.03       0.05622                0.03       0.1627                0.03       25644                0.03       0.4646                0.03       0.4651                0.8        100656                ≦0.4                         12.5657                0.4        100661                1.6        100667                6.3        25668                0.4        50669                0.03       0.8671                0.03       0.2675                0.1        25685                0.8        100699                50         100721                0.4        12.5724                0.4        0.4726                0.8        6.3815                0.03       &gt;100905                0.04       1001258               1.6        &gt;1001260               0.8        &gt;1001276               0.03       1.61276a              3.2        1001277               0.03       6.31277    HCl salt   0.03       3.21277a              6.3        1001278               ≦0.4                         &gt;1001300               ≦0.4                         6.31377               1.6        1001451               &gt;100       &gt;1001459               &gt;100       &gt;1001487               0.4        6.31527               0.4        6.3StandardsAmphotericin B 0.33 ± 0.2                     1.4 ± 0.5Nystatin       1.3 ± 0 3.0 ± 1.05-Fluorocytosine          0.14 ± 0.1                     5.7 ± 4.0Ketoconazole   ≦0.1                     11.0 ± 5.0Miconazole     ≦0.1                     1.3 ± 0______________________________________ *MIC values of the standard drugs are the mean of five determinations ±  Standard deviation 
    
     
                       TABLE 6______________________________________In Vivo Antifungal Results% Survival (150 mg/kg per day)Primary AssayEx.          DaysNo.          7           14     21______________________________________1            100         100    802            100         100    803            100         100    604            100         50     N.T.6            50          10     010           20          10     015           100         90     6016           100         100    10017           100         90     7025           100         100    5026           100         100    10026 salt      100         90     8027           100         100    10028           100         90     N.T.32           100         90     5033           100         100    10034           100         100    10034 salt      100         100    10035           100         100    9035 salt      100         100    7039           100         80     N.T.40           100         100    N.T.41           100         100    N.T.42           80          80     5047           90          80     3049           100         90     6050           100         90     5051           100         100    8052           100         100    9052 salt      100         100    9055           100         70     5065           100         70     5067           100         100    10085           100         80     7094           100         40     1099           100         100    40100          100         50     30101          100         90     60114          70          10     10117          60          0      0163          90          60     40164          100         80     70208          0           0      0286          100         50     20359          100         80     80360          100         60     40361          100         100    90363          10          0      0453          60          40     30594          70          10     0596          70          60     40603          10          0      0608          100         70     20620          100         100    90622          100         100    100627          0           0      0644          80          70     50646          100         100    70651          100         50     20656          100         90     40657          0           0      0661          50          20     0667          10          0      0668          70          10     0669          100         100    100671          100         100    60675          100         60     0685          30          10     0721          100         30     30724          100         90     40725          90          90     40726          100         80     10905          80          50     201276         100         70     501276a        0           0      01277         100         100    901277a        80          0      01278         0           0      01487         100         100    701527         100         70     20StandardsAmphotericin B        100         100    100Ketoconazole 100         80     50______________________________________ N.T.: Not Tested 
    
     DOSAGE FORMS 
     The antimycotic agents of this invention can be administered by any means that effects contact of the active ingredient with the agent&#39;s site of action in the body. The compounds can be administered by any conventional means available for use in conjunction with pharmaceuticals, either as individual therapeutic agents or in a combination of therapeutic agents. They can be administered alone, but are generally administered with a pharmaceutical carrier selected on the basis of the chosen route of administration and standard pharmaceutical practice. 
     The dosage administered will, of course, vary depending on the use and known factors such as the pharmacodynamic characteristics of the particular agent, and its mode and route of administration: age, health, and weight of the recipient; nature and extent of symptoms, kind of concurrent treatment, frequency of treatment, and the effect desired. 
     Dosage forms (compositions) suitable for administration contain from about 200 milligram to about 2000 milligrams of active ingredient per unit. In these pharmaceutical compositions, the active ingredient will ordinarily be present in an amount of about 0.5-95% by weight based on the total weight of the composition. For use in the treatment of said diseases, a daily dose of active ingredient can be about 10 to 50 milligrams per kilogram of body weight. 
     The composition of the invention may be in a conventional pharmaceutical form suitable for oral administration, for example a tablet, a capsule, an emulsion or an aqueous or oily solution or suspension, or suitable for topical application, for example a cream, ointment or gel. It can also be administered parenterally in sterile liquid dosage forms. 
     Gelatin capsules contain the active ingredient and powdered carriers, such as lactose, starch, cellulose derivatives, magnesium stearate, stearic acid and the like. Similar diluents can be used to make compressed tablets. Both tablets and capsules can be manufactured as sustained release products to provide for continuous release of medication over a period of hours. Compressed tablets can be sugar coated or film coated to mask any unpleasant taste and protect the tablet from the atmosphere, or enteric coated for selective disintegration in the gastrointestinal tract. 
     The pharmaceutical compositions which are ointments, creams and gels can, for example, contain the usual diluents, e.g. animal and vegetable fats, waxes, paraffins, starch, tragacanth, cellulose derivatives, polyethylene glycols, silicones, bentonites, silicic acid, talc and zinc oxide or mixtures of these substances. 
     In general, water, a suitable oil, saline, aqueous dextrose (glucose), and related sugar solutions and glycols such as propylene glycol or polyethylene glycols are suitable carries for parenteral solutions. Solutions for parenteral administration preferably contain a water soluble salt of the active ingredient, suitable stabilizing agents, and if necessary, buffer substances. Antioxidizing agents such as sodium bisulfite, sodium sulfite, or ascorbic acid, either alone or combined, are suitable stabilizing agents. 
     All the pharmaceutical compositions according to the invention can also contain coloring and flavoring to increase patient acceptance. 
     Also used are citric acid and its salts and sodium EDTA. In addition, parenteral solutions can contain preservatives, such as benzalkonium chloride, methyl or propyl-paraben, and chlorobutanol. 
     Suitable pharmaceutical carries are described in Remington&#39;s Pharmaceutical Sciences, A. Osol, a standard reference text in this field. 
     Useful pharmaceutical dosage forms for administration of the compounds of this invention can be illustrated as follows: 
     Capsules 
     A large number of unit capsules are prepared by filling standard two-piece hard gelatin capsules each with 100 milligrams of powdered active ingredient, 150 milligrams of lactose, 50 milligrams of cellulose, and 6 milligrams magnesium stearate. 
     Soft Gelatin Capsules 
     A mixture of active ingredient in a digestable oil such as soybean oil, cottonseed oil or olive oil is prepared and injected by means of a positive displacement pump into gelatin to form soft gelatin capsules containing 100 milligrams of the active ingredient. The capsules are washed and dried. 
     Tablets 
     A large number of tablets are prepared by conventional procedures so that the dosage unit is 100 milligrams of active ingredient, 0.2 milligrams of collodial silicon dioxide, 5 milligrams of magnesium stearate, 275 milligrams of microcrystalline cellulose, 11 milligrams of starch and 98.8 milligrams of lactose. Appropriate coatings may be applied to increase palatability or delay absorption. 
     Injectable 
     A parenteral composition suitable for administration by injection is prepared by stirring 1.5% by weight of active ingredient in 10% by volume propylene glycol. The solution is made to volume with water for injection and sterilized. 
     Suspension 
     An aqueous suspension is prepared for oral administration so that each 5 milliliters contain 100 milligrams of finely divided active ingredient, 100 milligrams of sodium carboxymethyl cellulose, 5 milligrams of sodium benzoate, 1.0 grams of sorbitol solution, U.S.P., and 0.025 milliliters of vanillin. 
     Cream 
     A cream for topical application is prepared by incorporating 100 milligrams of the finely pulverized active ingredient in 5 grams of a cream base which comprises 40% white petrolatum, 3% microcrystalline wax, 10% lanolin, 5% Span® 20, 0.3% Tween® 20 and 41.5% water. 
     Agricultural Formulations 
     The compounds of this invention when used for agricultural purposes will generally be used in formulation with a liquid or solid diluent or with an organic solvent. Useful formulations of the compounds of Formula I can be prepared in conventional ways. They include dusts, granules, pellets, solutions, emulsions, wettable powders, emulsifiable concentrates and the like. Many of these may be applied directly. Sprayable formulations can be extended in suitable media and used at spray volumes of from about one to several hundred liters per hectare. High strength compositions are primarily used as intermediates for further formulation. The formulations, broadly, contain about 1% to 99% by weight of active ingredient(s) and at least one of (a) about 0.1% to 35% surfactant(s) and (b) about 5% to 99% solid or liquid inert diluent(s). More specifically, they will contain these ingredients in the following approximate proportions: 
     
         ______________________________________       Active  Percent of Weight       Ingredient               Diluent(s)                         Surfactant(s)______________________________________Wettable Powders         20-90      0-74     1-10Oil Suspensions,          5-50     40-95     0-35Emulsions, Solutions,(including EmulsifiableConcentrates)Aqueous Suspensions         10-50     40-84     1-20Dusts          1-25     70-99     0-5Granules and Pellets          1-95      5-99     0-15High Strength 90-99      0-10     0-2Compositions______________________________________ 
    
     Lower or higher levels of active ingredient can, of course, be present depending on the intended use and the physical properties of the compound. Higher ratios of surfactant to active ingredient are sometimes desirable, and are achieved by incorporation into the formulation or by tank mixing. 
     Typical solid diluents are described in Watkins, et al., &#34;Handbook of Insecticide Dust Diluents and Carriers&#34;, 2nd Ed., Dorland Books, Caldwell, N.J. The more absorptive diluents are preferred for the wettable powders and the denser ones for dusts. Typical liquid diluents and solvents are described in Marsden, &#34;Solvents Guide,&#34; 2nd Ed., Interscience, New York, 1950. Solubility under 0.1% is preferred for suspension concentrates; solution concentrates are preferably stable against phase separation at 0° C. &#34;McCutcheon&#39;s Detergents and Emulsifiers Annual&#34;, MC Publishing Corp., Ridgewood, N.J., as well as Sisely and Wood, &#34;Encyclopedia of Surface Active Agents&#34;, Chemical Publ. Co., Inc., New York 1964, list surfactants and recommended uses. All formulations can contain minor amounts of additives to reduce foam, caking, corrosion, microbiological growth, etc. Preferably, ingredients should be approved by the U.S. Environmental Protection Agency for the use intended. 
     The methods of making such compositions are well known. Solutions are prepared by simply mixing the ingredients. Fine solid compositions are made by blending and, usually, grinding as in a hammer or fluid energy mill. Suspensions are prepared by wet milling (see, for example, Littler, U.S. Pat. No. 3,060,084). Granules and pellets may be made b spraying the active material upon preformed granular carriers or by agglomeration techniques. See J. E. Browning, &#34;Agglomeration&#34;, Chemical Engineering, Dec. 4, 1967, pp. 147ff. Rnd &#34;Perry&#39;s Chemical Engineer&#39;s Handbook&#34;, 4th Edn., McGraw-Hill, N.Y., 1963, pp. 8-59ff. 
     For further information regarding the art of formulation, see for example: 
     H. M. Loux, U.S. Pat. Nos. 3,235,361, Feb. 15, 1966, Col. 6, Line 16 through Col. 7, Line 19 and Examples 10 though 41. 
     R. W. Luckenbaugh, U.S. Pat. No. 3,309,192, Mar. 14, 1967, Col. 5, Line 43 through Col 7, Line 62 and Examples 8, 12, 15, 39, 41, 52, 53, 58, 132, 138-140, 162-164, 166, 167, 169-192. 
     H. Gysin and E. Knusli, U.S. Pat. No. 2,891,855, June 23, 1959, Col. 3, Line 66 through Col. 5, Line 17 and Examples 1-4. 
     G. C. Klingman, &#34;Weed Control as a Science&#34;, John Wiley and Sons, Inc., New York, 1961, pp. 81-96. 
     J. D. Fryer and S. A. Evans, &#34;Weed Control Handbook&#34;, 5th Edn. Blackwell Scientific Publications, Oxford, 1968, pp. 101-103. 
     Examples of useful formulations of compounds of the present invention are as follows. 
     Wettable Powder 
     
         ______________________________________2-(2,4-difluorophenyl)-3-(4-fluorophenyl)-1-(1H-1,2,4-                       80%triazol-1-yl)-3-buten-1-ol; and the (S) enantiomerthereofsodium alkylnaphthalenesulfonate                       2%sodium ligninsulfonate      2%synthetic amorphous silica  3%kaolinite                   13%______________________________________ 
    
     The ingredients are blended, hammer-milled, reblended and packaged. 
     Granule 
     
         ______________________________________wettable powder of above example                  15%gypsum                 69%potassium sulfate      16%______________________________________ 
    
     The ingredients are blended in a rotating or fluid bed mixer and water sprayed on to accomplish granulation. When most of the material has reached the desired range of 1.0 to 0.42 mm. (U.S.S. No. 18 to 40 sieves), the granules are removed, dried, and screened. Oversize material is crushed to produce additional material in the desired range. 
     High Strength Concentrate 
     
         ______________________________________2-(2-fluorophenyl)-3-(4-fluorophenyl)-1-(1H-1,2,4-                     98.5%triazol-1-yl)-3-buten-2-ol; and the (S) enantiomerthereofsilica aerogel            0.5%synthetic amorphous fine silica                     1.0%______________________________________ 
    
     The ingredients are blended and ground in a hammer-mill to produce a high strength concentrate essentially all passing a U.S.S. No. 50 sieve (0.3 mm openings). This material may then be formulated in a variety of ways. 
     Aqueous Suspensions 
     
         ______________________________________2-(2,4-difluorophenyl)-3-phenyl-1-(1H-1,2,4-                      25%triazol-1-yl)-3-buten-2-ol; and the (S)enantiomer thereofhydrated attapulgite       3%crude calcium ligninsulfonate                      10%sodium dihydrogen phospate 0.5%water                      61.5%______________________________________ 
    
     The ingredients are ground together in a ball, sand, or roller mill until the solid particles have been reduced to diameters under 10 microns. 
     Solution 
     
         ______________________________________2-(2,4-difluorophenyl)-3-(4-chlorophenyl)-l-(1H-                      30%1,2,4-triazol-1-yl)-3-buten-2-ol; and the (S)enantiomer thereofdimethylformamide          70%______________________________________ 
    
     The ingredients are combined and stirred to produce a solution, which can be used for low volume applications. 
     Emulsifiable Concentrate 
     
         ______________________________________2-(2,4-difluorophenyl)-3-(4-fluorophenyl)-1-(1H-                      15%1,2,4-triazol-1-yl)-3-buten-2-ol; and the (S)enantiomer thereofblend of calcium sulfonates                      25%and nonionic surfacantsxylene                     60%______________________________________ 
    
     The ingredients are combined and stirred until the active is dissolved. A fine screen filter is included in packaging operation to insure the absence of any extraneous undissolved material in the product. 
     Utility 
     The compounds of this invention are useful as plant disease control agents. They are effective in controlling a broad spectrum of plant diseases, particularly foliar pathogens of ornamental, vegetable, field, cereal and fruit crops, such as Puccinia recondita, Erysiphe cichoracearum, Erysiphe graminis, Venturia inaequalis, Cercospora arachidicola, and Monilinia fructicola, Rhizoctonia solani, Pyricularia oryzae, Botrytis cinerea, Pseudocercosporella herpotrichlorides, and Cercosporidium personatum. They also control seed pathogens. 
     Disease control is ordinarily accomplished by applying an effective amount of the compound either pre- or post-infection to the portion of the plant to be protected, such as the roots, stems, foliage, fruit, seeds, tubers or bulbs, or to the media (soil or sand) in which the plants to be protected are growing. The compound may also be applied to the seed from which the plants to be protected are to be grown. 
     Rates of application for these compounds can be influenced by many factors of the environment and should be determined under actual use conditions. Foliage can normally be protected when treated at a rate of from less than 1 g/ha to 5000 g/ha of active ingredient. Plants growing in soil treated at a concentration from 0.1 to about 20 kg/ha can be protected from disease. Seed and seedlings can normally be protected when seed is treated at a rate of from 0.06 to about 3 grams per kilogram of seed. 
     The compounds of this invention can be mixed with fungicides, bactericides, acaricides, nematicides, insecticides, or other biologically active compounds in order to achieve desired results with a minimum expenditure of time, effort and material. Amounts of these biologically active materials added for each part by weight of the composition of this invention may vary from 0.05 to 25 parts by weight. Suitable agents of this type are well-known to those skilled in the art. Some are listed below: 
     Fungicides 
     methyl 2-benzimidazolecarbamate (carbendazim) 
     tetramethylthiuram disulfide (thiuram) 
     n-dodecylguanidine acetate (dodine) 
     manganese ethylenebisdithiocarbamate (maneb) 
     1,4-dichloro-2,5-dimethoxybenzene (chloroneb)methyl 
     1-(butylcarbamoyl)-2-benzimidazolecarbamate (benomyl) 
     2-cyano-n-ethylcarbamoyl-2-methoxyiminoacetamide (cymoxanil) 
     N-trichloromethylthiotetrahydrophthalamide (captan) 
     N-trichloromethylthiophthalimide (folpet) 
     dimethyl 4,4&#39;-(o-phenylene)bis(3-thioallophanate)(thiophanate-methyl) 
     2-(thiazol-4-yl)benzimidazole (thiabendazole) 
     aluminum tris(O-ethyl phosphonate)(phosethyl aluminum) 
     tetrachloroisophthalonitrile (chlorothalonil) 
     2,6-dichloro-4-nitroaniline (dichloran) 
     N-(2,6-dimethylphenyl)-N-(methoxyacetyl)alanine methyl ester (metalaxyl) 
     cis-N-[1,1,2,2-tetrachloroethyl)thio]cyclohex-4-ene-1,2-dicarbioximide (captafol) 
     3-(3,5-dichlorophenyl)-N-(1-methylethyl)-2,4-dioxo-1-imidazolidine carboxamide (iprodione) 
     3-(3,5-dichlorophenyl)-5-ethenyl-5-methyl-2,4-oxazolidinedione (vinclozolin) 
     kasugamycin 
     O-ethyl-S,S-diphenylphosphorodithioate(edifenphos) 
     4-(3-(4-(1,1-dimethyl-ethyl)phenyl)-2-ethyl)propyl-2,6-dimethylmorpholine (Fenpropimorph) 
     4-(3-4(1,1-dimethyl-ethyl)phenyl)-2-methyl)propylpiperidine (Fenpropidine) 
     Bactericides 
     tribasic copper sulfate 
     streptomycin sulfate 
     oxytetracycline 
     Acaricides 
     senecioic acid, ester with 2-sec-butyl-4,6-dinitrophenol (binapacryl) 
     6-methyl-1,3-dithiolo[2,3-B]quinonolin-2-one (oxythioquinox) 
     2,2,2-trichloro-1,1-bis(4-chlorophenyl)ethanol(dicofol) 
     bis(pentachloro-2,4-cyclopentadien-1-yl)(dienochlor) 
     tricyclohexyltin hydroxide (cyhexatin) 
     hexakis(2-methyl-2-phenylpropyl)distannoxane (fenbutin oxide) 
     Nematicides 
     2-]diethoxyphosphinylimino]-1,3-diethietane (fosthietan) 
     S-methyl-1-(dimethylcarbamoyl)-N-(methylcarbamoyloxy)thioformimidate(oxamyl 
     S-methyl-1-carbamoyl-N-(methylcarbamoyloxy)thioformimidate 
     N-isopropylphosphoramidic acid, O-ethyl-O&#39;-[4-(methylthio)-m-tholyl]diester (fenamiphos) 
     Insecticides 
     3-hydroxy-N-methylcrotonamide(dimethylphosphate)ester (monocrotophos) 
     methylcarbamic acid, ester with 2,3-dihydro-2,2-dimethyl-7-benzofuranol (carbofuran) 
     O-[2,4,5-trichloro-α-(chloromethyl)benzyl]phosphoric acid, O&#39;,O&#39;-dimethyl ester (tetrachlorvinphos) 
     2-mercaptosuccinic acid, diethyl ester, S-ester with thionophosphoric acid, dimethyl ester (malathion) 
     phosphorothioic acid, O,O-dimethyl, O-p-nitrophenyl ester (methyl parathion) 
     methylcarbamic acid, ester with α-naphthol (carbaryl) 
     methyl N-[[(methylamino)carbonyl]oxy]ethanimidothioate (methomyl) 
     N&#39;-(4-chloro-o-tolyl)-N,N-dimethylformamidine (chlordimeform) 
     O,O-diethyl-O-(2-isopropyl-4-methyl-6-pyrimidyl)phosphorothioate (diazinon) 
     octachlorocamphene (toxaphene) 
     O-ethyl O-p-nitrophenyl phenylphosphonothioate (EPN) 
     cyano(3-phenoxyphenyl)-methyl 4-chloro-α-(1-methylethyl)benzeneacetate (fenvalerate) 
     (3-phenoxyphenyl)methyl (+)-cis,trans-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropanecarboxylate (permethrin) 
     dimethyl N,N&#39;-[thiobis(N-methylimmo)carbonyloxy]]-bis]ethanimidothioate] (thiodicarb) 
     phosphorothiolothionic acid, O-ethyl-O-[4-(methylthio)phenyl]-S-n-propyl ester (sulprofos) α-cyano-3-phenoxybenzyl 3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropane carboxylate (cypermethrin) 
     cyano(3-phenoxyphenyl)methyl 4-(difluoromethoxy)-α0(methylethyl)benzeneacetate (flucythrinate) 
     O,O-diethyl-O-(3,5,6-trichloro-2-pyridyl)phosphorothioate (chlorpyrifos) 
     O,O-dimethyl-S-[(4-oxo-1,2,3-benzotriazin-3-(4H)-yl)-methyl]phosphorodithioate (azinphos-methyl) 
     5,6-dimethyl-2-dimethylamino-4-pyrimidinyl dimethyl carbamate (pirimicarb) 
     S-(N-formyl-N-methylcarbamoylmethyl)-O,O-dimethyl phosphorodithioate (formothion) 
     S-2-(ethylthioethyl)-O,O-dimethyl phosphiorothioate (demeton-S-methyl) 
     α-cyano-3-phenoxybenzyl cis-3-(2,2-dibromovinyl)-2,2-dimethylcyclopropane carboxylate (deltamethrin) 
     cyano(3-phenoxyphenyl)methyl ester of N-(2-chloro-4-trifluoromethylphenyl)alanine (fluvalinate) 
     Test results indicate that the compounds of the present invention are also active preemergent or postemergent herbicides or plant growth regulants. Some of them have utility for broad-spectrum pre- and/or postemergence weed control in areas where complete control of all vegetation is desired, such as around industrial storage areas, parking lots, drive-in theaters, around billboards, highway and railroad structures. Other compounds have utility for selective weed control in crops such as rice, wheat, barley, corn, soybeans, sugarbeets and cotton. Some of the compounds are useful as selective herbicides for rice. They may be used either in direct seeded or transplanted rice. Alternatively, the subject compounds are useful to modify plant growth. 
     The rates of application for the compounds of the invention are determined by a number of factors, including their use as plant growth modifiers or as herbicides, the crop species involved, the types of weeds to be controlled, weather and climate, formulations selected, mode of application, amount of foliage present, etc. In general terms, the subject compounds should be applied at levels of around 0.050 to 20 kg/ha, the lower rates being suggested for use on lighter soils and/or those having a low organic matter content, for plant growth modification or for situations where only short-term persistence is required, such as a herbicide for fallow land. 
     The compounds of the invention may be used in combination with any other commercial herbicide, nonlimiting examples of which are those below: 
     
         ______________________________________        Chemical Name______________________________________Common Nameacifluorfen    5-[2-chloro-4-(trifluoromethyl)-          phenoxy]-2-nitrobenzoic acidacrolein       acroleinalachlor       2-chloro-2&#39;,6&#39;-diethyl-N-          (methoxymethyl)-acetanilideametryn        2-(ethylamino)-4-(isopropylamino)-6-          methylthio)- .sub.- s-triazineamitrole       3-amino- .sub.- s-triazoleAMS            ammonium sulfamateasulam         methyl sulfanilylcarbamateatrazine       2-chloro-4-(ethylamino)-6-          (isopropylamino)- .sub.- s-triazinebarban         4-chloro-2-butynyl  .sub.-- m-          chlorocarbanilatebenefin        N-butyl-N-ethyl-α,α,α-trifluoro-2,6-          dinitro- -p-toluidinebensulide      0,0-diisopropyl phosphorodithioate          S-ester with N-(2-mercaptoethyl)-          benzenesulfonamidebentazon       3-isopropyl-1H-2,1,3-          benzothiadiazin-4(3H)-one 2,2-          dioxidebenzipram      3,5-dimethyl-N-(1-methylethyl)-N-          (phenylmethyl)benzamidebenzoylprop    N-benzoyl-N-(3,4-dichlorophenyl)-DL-          alainebifenox        methyl 5-(2,4-dichlorophenoxy)-2-          nitrobenzoatebromacil       5-bromo-3-sec-butyl-6-methyluracilbromoxynil     3,5-dibromo-4-hydroxybenzonitrilebutachlor      N-(butoxymethyl)-2-chloro-2&#39;,6&#39;-          diethylacetanilidebutam          2,2-dimethyl-N-(1-methylethyl)-N-          (phenylmethyl)propanamidebuthidazole    3-[5-(1,1-dimethylethyl)-1,3,4-          thiadiazol-2-yl]-4-hydroxy-1-          methyl-2-imidazolidinonebutralin       4-(1,1-dimethylethyl)-N-(1-methyl-          propyl)-2,6-dinitrobenzenaminebutylate       S-ethyl-diisobutylthiocarbamatecacodylic acid hydroxydimethylarsine oxidecarbetamide    D-N-ethyllactamide carbanilate          (ester)CDAA           N-N-diallyl-2-chloroacetamideCDEC           2-chloroallyl diethyldithiocarbamatechlorbromuron  3-(4-bromo-3-chlorophenyl)-1-          methoxy-1-methylureachloroxuron    3-[ -p-( -p-chlorophenoxy)phenyl] 9 -1,1-          dimethylureachloropropham  isoproyl  .sub.-- m-chlorocarbanilatechlorsulfuron  2-chloro-N-[(4-methoxy-6-methyl]-          1,3,5-triazin-2-yl)amino-          carbonyl]benzene-sulfonamidechlortoluron   N&#39;-(3-chloro-4-methylphenyl-N&#39;,N&#39;-          dimehylureacisanilide     cis-2,5-dimethyl-N-phenyl-1-          pyrrolidine-carboxamideCMA            calcium methanearsonatecyanazine      2-[[4-chloro-6-(ethylamino)- .sub.- s-          triazin-2-yl]amino]-2-          methylpropionitrilecycloate       S-ethyl N-ethylthiocyclohexane-          carbamatecycluron       3-cyclooctyl-1,1-dimethylureacyperquat      1-methyl-4-phenylpyridiniumcyprazine      2-chloro-4-(cyclopropylamino)-6-          (isopropylamino)- .sub.- s-triazinecyprazole      N-[5-(2-chloro-1,1-dimethylethyl)-          1,3,4-thiadiazol-2-yl]          cyclopropanecarboxamidecypromid       3&#39;,4&#39;-dichlorocyclopropanecar-          boxanilidedalapon        2,2-dichloropropionic aciddazomet        tetrahydro-3,5-dimethyl-2H-1,3,5-          thiadiazine-2-thioneDCPA           dimethyl tetrachloroterephthalatedesmetryn      2-(isopropylamino)-4-(methylamino)-          6-methylthio)- .sub.- s-triazinediallate       S-(2,3-dichloroallyl)diisopropyl-          thiocarbamatedicamba        3,6-dichloro- -o-anisic aciddichlobenil    2,6-dichlorobenzonitriledichlorprop    2-(2,4-dichlorophenoxy)propionic          aciddiclofop       2-[4-(2,4-dichlorophenoxy)phenoxyl]-          propanoic aciddiethatyl      N-(chloroacetyl)-N-(2,6-          diethylphenyl)-glycinedifenzoquat    1,2-dimethyl-3,5-diphenyl-1H-          pyrazoliumdinitramine    N.sup.4,N.sup.4 -diethyl-α,α,α-trifluoro-          3,5-          dinitrotoluene-2,4-diaminedinoseb        2-sec-butyl-4,6-dinitrophenoldiphenamide    N,N-dimethyl-2,2-diphenylacetamidedipropetryn    2-(ethylthio)-4,6-bis(isopropyl-          amino)- .sub.- s-triazinediquat         6,7-dihydrodipyrido[1,2,-α:2&#39;,1&#39;-c]-          pyrazinediium iondiuron         3-(3,4-dichlorophenyl)-1,1-          dimethylureaDSMA           disodium methanearsonateendothall      7-oxabicyclo[2.2.1]heptane-2,3-          dicarboxylic aciderbon          2-(2,4,5-trichlorophenoxy)ethyl 2.2-          dichloropropionateethafluralin   N-ethyl-N-(2-methyl-2-propenyl)-2,6-          dinitro-4-(trifluoromethyl)-          benzenamineethofumesate   (±)-2-ethoxy-2,3-dihydro-3,3-          dimethyl-5-benzofuranyl          methanesulfonatefenac          (2,3,6-trichlorophenyl)acetic acidfenoxaprop     ethyl 2-(4-(6-chloro-2-benzoxazolyl-          oxy)phenoxy)propanoatefenuron        1,1-dimethyl-3-phenylureafenuron TCA    1,2-dimethyl-3-phenylurea          mono(trichloroacetate)flamprop       N-benzoyl-N-(3-chloro-4-          fluorophenyl)-DL-anilinefluchloralin   N-(2-chloroethyl)-2,6-dinitro-N-          propyl-4-(trifluoromethyl)anilinefluometuron    1,1-dimethyl-3-(α,α,α-trifluoro- .sub.--          -          tolyl)-ureafluorodifen     -p-nitrophenyl α,α,α-trifluoro-2-          nitro- -p-tolyl etherfluridone      1-methyl-3-phenyl-5-[3-(trifluoro-          methyl)phenyl]-4-(1H)-pyridinonefomesafen      5-(2-chloro-4-trifluoromethyl-          phenoxy)-N-methylsulfonyl-2-          nitrobenzamidefosamine       ethyl hydrogen (aminocarbonyl)-          phosphonateglyphosate     N-(phosphonomehyl)glycinehexaflurate    potasium hexafluoroarsenatehexazinone     3-cyclohexyl-6-(dimethylamino)-1-          methyl-1,3,5-triazine-2,4(1H, 3H)-          dioneimazaquin      2-(4,5-dihydro-4-methyl-4-(1-methyl-          ethyl)-5-oxo-1H-imidazol-2-yl)-3-          quinolinecarboxylic acidioxynil        4-hydroxy-3,5-diiodobenzonitrileisopropalin    2,6-dinitro-N,N-dipropylcumidinekarbutilate    tert-butylcarbamic acid ester with          3-( .sub.-- m-hydroxyphenyl)-1,1-          dimethylurealactofen       1&#39;-(carboethoxy)ethyl-5-(2-chloro-4-          (trifluoromethyl)phenoxy)-2-          nitrobenzoatelenacil        3-cyclohexyl-6,7-dihydro-1H-          cyclopentapyrimidine-2,4(3H,5H)-          dionelinuron        3-(3,4-dichlorophenyl)-1-methoxy-1-          methylureaMAA            methanearsonic acidMAMA           monoammonium methanearsonateMCPA           [(4-chloro- -o-tolyl)oxy]acetic acidMCPB           4-[(4-chloro- -o-tolyl)oxy]butyric          acidmecoprop       2-[(4-chloro- -o-tolyl)oxy]propionic          acidmefluidide     N-[(2,4-dimethyl-5-          [[(trifluoromethyl)-          sulfonyl]amino]phenyl]acetamidemethalpropalin N-(2-methyl-2-propenyl)-2.6-dinitro-          N-propyl-4-(trifluoromethyl)-          benzenamidemethabenzthiazuron          1,3-dimethyl-3-(2-benzothiazolyl)          ureametham         sodium methyldithiocarbamatemethazole      2-(3,4-dichlorophenyl)-4-methyl-          1,2,4-oxadiazolidine-3,5-dionemethoxuron     N&#39;-(3-chloro-4-methoxyphenyl)N,N-          dimethylureametolachlor    2-chloro-N-(2-ethyl-6-methylphenyl)-          N-(2-methoxy-1-methylethyl)-          acetamidemetribuzin     4-amino-6-tert-butyl-3-(methylthio)-          as-triazine-5(4H)-onemetsulfuron methyl          2-[[(4-methoxy-6-methyl-1,3,5-          triazine-2-yl)aminocarbonyl]amino-          sulfonyl]benzoic acid, methyl          estermolinate       S-ethyl hexahydro-1H-azepine-1-          carbothioatemonolinuron    3-( -p-chlorophenyl)-1-methoxy-1-          methylureamonuron        3-( -p-chlorophenyl)-1,1-dimethylureamonuron TCA    3-( -p-chlorophenyl)-1,1-dimethylurea          mono(trichloroacetate)MSMA           monosodium methanearsonatenapropamide    2-(α-naphthoxy)-N,N-          diethylpropionamidenaptalam       N-1-naphthylphthalamic acidneburon        1-butyl-3-(3,4-dichlorophenyl)-1-          methylureanitralin       4-(methylsulfonyl)-2,6-dinitro-N,N-          dipropylanilinenitrofen       2,4-dichlorophenyl  -p-nitrophenyl          ethernitrofluorofen 2-chloro-1-(4-nitrophenoxy)-4-          (trifluoromethyl)benzenenorea          3-(hexahydro-4.7-methanoindan-5-yl)-          1.1-dimethylureanorflurazon    4-chloro-5-(methylamino)-2-(α,α,α-          trifluoro- .sub.-- m-tolyl)-3(2H)-          pyridazinoneoryzalin       3,4-dinito-N,N-dipropylsulfanilamideoxadiazon      2-tert-butyl-4-(2,4-dichloro-5-          isopropoxyphenyl)Δ.sup.2 -1,3,4-          oxadiazolin-5-oneoxyfluorfen    2-chloro-1-(3-ethoxy-4-nitro-          phenoxy)-4-(trifluoro-          methyl)benzeneparaquat       1,1&#39;-dimethyl-4,4&#39;-bipyridinium ionPBA            chlorinated benzoic acidpendimethalin  N-(1-ethylpropyl)-3,4-dimethyl-2,6-          dinitrobenzenamineperfluidone    1,1,1-trifluoro-N-[2-methyl-4-          (phenylsulfonyl)phenyl]methane-          sulfonamidepicloram       4-amino-3,5,6-trichloropicolinic          acidprocyazine     2-[[4-chloro-6-(cyclopropylamino)-          1,3,5-triazine-2-yl]amino]-2-          methylpropanenitrileprofluralin    N-(cyclopropylmethyl)-α,α,α-          trifluoro-2,6-dinitro-N-propyl- -p-          toluidineprometon       2,4-bis(isopropylamino)-6-methoxy- .sub.- s-          triazineprometryn      2,4-bis(isopropylamino)-6-          (methylthio)- .sub.- s-triazinepronamide      3,5-dichloro N-(1,1-dimethyl-2-          propyn-yl)enzamidepropachlor     2-chloro-N-isopropylacetanilidepropanil       3&#39;,4&#39;-dichloroprionalidepropazine      2-chloro-4,6-bis(isopropylamino)- .sub.- s-          triazinepropham        isopropyl carbanilateprosulfalin    N-[[4-(dipropylamino)-3,5-          dinitrophenyl]sulfonyl]-S,S-          dimethylsulfilimineprynachlor     2-chloro-N-(1-methyl-2-          propynyl)acetanilidequinofop ethyl 2-[4-(6-chloroquinoxalin-2-yloxy)-          phenoxypropanoic acid, ethyl estersecbumeton     N-ethyl-6-methoxy-N&#39;(1-          methylpropyl)-1,3,5-triazine-2,4-          diaminesethoxydim     2-[1-(ethoxyimino)butyl]-5-[2-          (ethylthio)propyl]-3-hydroxy-2-          cyclohexene-1-onesiduron        1-(2-methylcyclohexyl)-3-phenylureasimazine       2-chloro-4,6-bis(ethylamino)- .sub.- s-          triazinesimetryn       2,4-bis(ethylamino)-6-(methylthio)-           .sub.- s-triazinesupriox        2-[1-(2,5-dimethylphenyl)-          ethylsulfonyl]-pyridine-N-oxideTCA            trichloroacetic acidtebuthiuron    N-[5-(1,1-dimethylethyl)-1,3,4-          thiadiazol-2-yl]-N,N&#39;-dimethylureaterbacil       3-tert-butyl-5-chloro-6-methyluracilterbuchlor     N-(butoxymethyl)-2-chloro-N-[2-(1.1-          dimethylethyl)-6-methylphenyl]-          aceamideterbuthylazine 2-(tert-butylamino)-4-chloro-6-          (ethylamino)- .sub.- s-triazineterbutol       2,6-di-tert-butyl- -p-tolyl          methylcarbamateterbutryn      2-(tert-butylamino)-4-(ethylamino)-          6-(methylthio)- .sub.- s-triazinetetrafluron    N,N-dimethyl-N&#39;-[3-(1,1,2,2,-          tetrafluoroethoxy)phenyl]ureathiobencarb    S-[(4-chlorophenyl)methyl]          diethylcarbamothioatetriallate      S-(2,3,3-trichloroallyl)-          diisopropylthiocarbamatetrifluralin    α,α,α-tifluoro-2,6-dinitro-N,N-          propyl- -p-toluidinetrimeturon     1-( -p-chlorophenyl)-2,3,3-          trimethylpseudoureavernolate      S-propyl dipropylthiocarbamae ethyl          5-[2-chloro-4-(trifluoromethyl)-          phenoxy]-2-nitrobenzoic acid2,3,6-TBA      2,3,6-trichlorobenzoic acid2,4-D          (2,4-dichlorophenoxy)acetic acid2,4-DB         4-(2,4-dichlorophenoxy)butyric acid2,4-DEP        tris[2-(2,4-dichlorophenoxy)ethyl]          phosphiteTrade Name orCode Number&#34;Cinch&#34;        exo-1-methyl-4-(1-methylethyl)-2-[2-          methylphenyl)methoxy]7-          oxabicyclo[2.2.1]heptaneAC 263,499     2-[4,5-dihydro-4-methyl-4-(1-methyl-          ethyl)-5-oxo-1H-imidazol-2-yl]-5-          ethyl-3-pyridinecarboxylic acidHarmony ™   3-[[(4-methoxy-6-methyl-1,3-5-          triazin-2-yl)aminocarbonyl]amino-          sulfonyl]-2-thiophenecarboxylic          acid, methyl eserPPG-1013       5-(2-chloro-4-(trifluoromethyl)-          phenoxy)propanoic aicd, methyl          esterFMC 57020      2-(2&#39;-chlorophenyl)methyl-4,4-          dimethyl-3-isoxazolidinoneAC 222,293     6-(4-isopropyl-4-methyl-5-oxo-2-          imidazolin-2-yl)- .sub.-- m-toluic          acid, methyl ester and 6-(4-          isopropyl-4-methyl-5-oxo-2-          imidazolin-2-yl- -p-toluic acid,          methyl ester______________________________________ 
    
     The herbicidal properties of the subject compounds were discovered in a number of greenhouse tests. The test procedures and results follow. 
     This invention is further illustrated by the following examples. 
     EXAMPLE A 
     The test compounds were dissolved in acetone in an amount equal to 6% of the final volume and then suspended at a concentration of 100 or 20 ppm in purified water containing 250 ppm of the surfactant TREM 014 (polyhydric alcohol esters). This suspension was sprayed to the point of run-off on apple seedings. The following day plants were inoculated with a spore suspension of Venturia inaequlis, the causal agent of apple scab, and incubated in a saturated humidity chamber at 20° C. for 24 hours and then in a growth chamber at 22° C. for 11 days, when disease ratings were made. 
     EXAMPLE B 
     The test compounds were dissolved in acetone in an amount equal to 6% of the final volume and then suspended at a concentration of 100 or 20 ppm in purified water containing 250 ppm of the surfactant TREM 014 (polyhydric alcohol esters). This suspension was sprayed to the point of run-off on peanut seedlings. The following day plants were inoculated with a spore suspension of Cercosporidium personatum, the causal agent of Peanut Late Leafspot, and incubated in a saturated humidity chamber at 22° C. for 24 hours, then in a high humidity chamber at 27° C. for 7 days, and then in a growth chamber at 29° C. for 7 days, when disease ratings were made. 
     EXAMPLE C 
     The test compounds were dissolved in acetone in an amount equal to 6% of the final volume and then suspended at a concentration of 100 or 20 ppm in purified water containing 250 ppm of the surfactant TREM 014 (polyhydric alcohol esters). This suspension was sprayed to the point of run-off on broad bean seedlings. The following day plants were inoculated with a spore suspension of Botrytis cinerea, the causal agent of bean grey mold, and incubated in a saturated humidity chamber at 20° C. for 24 hours when disease ratings were made. 
     EXAMPLE D 
     The test compounds were dissolved in acetone in an amount equal to 6% of the final volume and then suspended at a concentration of 100 or 20 ppm in purified water containing 250 ppm of the surfactant TREM 014 (polyhydric alcohol esters). This suspension was sprayed to the point of run-off on wheat seedlings. The following day plants were inoculated with a spore dust of Erysiphe graminis f. sp. tritici, the causal agent of wheat powdery mildew, and incubated in a growth chamber at 20° C. for 6 days, when disease ratings were made. 
     EXAMPLE E 
     The test compounds were dissolved in acetone in an amount equal to 6% of the final volume and then suspended at a concentration of 100 or 20 ppm in purified water containing 250 ppm of the surfactant TREM 014 (polyhydric alcohol esters). This suspension was sprayed to the point of run-off on rice seedlings. The following day plants were inoculated with a spore suspension of Pyricularia oryzae, the causal agent of rice blast, and incubated in a saturated humidity chamber at 27° C. for 24 hours and then in a growth chamber at 29° C. for 4 days, when disease ratings were made. 
     EXAMPLE F 
     The test compounds were dissolved in acetone in an amount equal to 6% of the final volume and then suspended at a concentration of 100 or 20 ppm in purified water containing 250 ppm of the surfactant TREM 014 (polyhydric alcohol esters). This suspension was sprayed to the point of run-off on rice seedlings. The following day plants were inoculated with a spore suspension of Rhizoctonia solani, the causal agent of rice sheath blight, and incubated in a saturated humidity chamber at 27° C. for 48 hours and then in a growth chamber at 29° C. for 4 days, when disease ratings were made. 
     EXAMPLE G 
     The test compounds were dissolved in acetone in an amount equal to 6% of the final volume and the suspended at a concentration of 100 or 20 ppm in purified water containing 250 ppm of the surfactant TREM 014 (polyhydric alcohol esters). This suspension was sprayed to the point of run-off on wheat seedlings. The following day plants were inoculated with a spore suspension of Puccinia recondita, the causal agent of wheat leaf rust, and incubated in a saturated humidity chamber at 20° C. for 24 hours and then in a growth chamber at 20° C. for 8 days, when disease ratings were made. 
     EXAMPLE H 
     The test compounds were dissolved in acetone in an amount equal to 6% of the final volume and then suspended at a concentration of 100 or 20 ppm in purified water containing 250 ppm of the surfactant TREM 014 (polyhydric alcohol esters). This suspension was sprayed to the point of run-off on tomato seedlings. The following day plants were inoculated with a spore suspension of Phytophthora infestans, the causal agent of tomato late blight, and incubated in a saturated humidity chamber at 20° C. for 24 hours and then in a growth chamber at 20° C. for 5 days, when disease ratings were made. 
     EXAMPLE I 
     The test compounds were dissolved in acetone in an amount equal to 6% of the final volume and then suspended at a concentration of 100 or 20 ppm in purified water containing 250 ppm of the surfactant TREM 014 (polyhydric alcohol esters). This suspension was sprayed to the point of run-off on grape seedlings. The following day plants were inoculated with a spore suspension of Plasmorpara viticola, the causal agent of grade downy mildew, and incubated in a saturated humidity chamber at 20° C. for 24 hours, then in a growth chamber at 20° C. for 7 days and the held in a saturated humidity chamber at 20° C. for 24 hours, when disease ratings were made. 
     EXAMPLE J 
     The test compounds were dissolved in acetone so that 1 ml of solution yielded a concentration of 0.5 kilogram/hectare when added to cucumber seeds and soil in pots. Seeds and soil were then inoculated with a mixture of sand, cereal and mycelium of the fungus Pythium aphanadermatum, causal agent of cucumber damping off, and incubated in a growth chamber at 30° C. for 14 days. Disease ratings were then made. 
     EXAMPLE K 
     The test compounds were dissolved in acetone so that 1 ml of solution yielded a concentration of 0.5  kilogram/hectare when added to cotton seeds and soil in pots. Seeds and soil were then inoculated with a mixture of sand, cereal and mycelium of the fungus Rhizoctonia solani, causal agent of cotton blight, and incubated in a growth chamber at 30° C. for 14 days. Disease ratings were then made. 
     EXAMPLE L 
     The test compounds were dissolved in acetone so that 1 ml of solution yielded a concentration of 0.5 kilogram/hectare when added to cucumber seeds and soil in pots. Seeds and soil were then inoculated with a mixture of sand, cereal and mycelium of the fungus Fusarium oxysporum f. sp. cucumerinum, causal agent of cucumber wilt, and incubated in a growth chamber at 30° C. for 14 days. Disease ratings were then made. 
     EXAMPLE M 
     The test compounds were dissolved in acetone so that 1 ml of solution yielded a concentration of 0.5 kilogram/hectare when added to lima bean seeds and soil in pots. Seeds and soil were then inoculated with a mixture of sand, cereal and mycelium of the fungus Sclerotium rolfsii, causal agent of southern blight, and incubated in a growth chamber at 30° C. for 14 days. Disease ratings were then made. 
     Results for Examples A-M are given in Table 7. In this table, a rating of 100 indicates 100% disease control and a rating of 0 indicates no disease control relative to the controls. A - entry indicates that no test was performed with the specified compound. A P entry indicates that disease control was not measured due to phytoxicity. 
     
                                           TABLE 7__________________________________________________________________________Ex  Rate   Ex.      Ex.         Ex.            Ex.               Ex.                  Ex.                     Ex.                        Ex.                           Ex.                              Rate Ex.                                      Ex.                                         Ex.                                            Ex.No. (PPM)   A  B  C  D  E  F  G  H  I  (kg/ha)                                   J  K  L  M__________________________________________________________________________1   100 62 100         81 98 90 97 100                        0  12 5    0  P  0  P2   100 62 100         93 98 95 100                     100                        0  99 5    0  P  0  P3   100 100      100         93 93 5  93 100                        0  0  5    0  0  P  P4   100 100      100         88 100               96 100                     100                        0  81 5    0  0  P  06   100 0  82 84 98 0  0  96 23 0  5    0  0  P  010  100 0  76 52 63 0  17 64 0  0  5    0  0  0  015  100 100      100         99 100               1  93 100                        26 0  5    0  P  0  P16  100 -- -- 46 0  0  -- 0  23 5  0    0  P  0    20  74 99 27 67 0  0  100                        -- --17  100 -- -- 89 -- 0  81 -- 0  42 5    0  0  P  0    20  80 100         57 95 0  0  100                        -- --25  100 100      100         96 91 31 48 97 0  0  5    0  P  P  3526  100 100      100         96 86 31 61 97 23 86 5    0  25 25 3527  100 62 100         88 98 95 100                     100                        24 84 5    0  0  0  028  100 89 100         88 98 81 100                     100                        0  6  5    0  0  0  032  100 100      100         98 95 97 33 100                        0  98 5    0  0  P  P33  100 -- -- 56 -- 0  60 -- 0  24 5    0  0  0  0    20  47 99 37 89 0  29 100                        -- --34  100 69 100         94 60 86 16 66 0  0  5    0  0  0  035  100 100      100         96 100               0  100                     96 0  26 5    0  0  0  039  100 89 97 96 98 7  100                     100                        0  81 5    0  0  0  040  100 19 100         80 91 7  61 96 0  0  5    0  0  0  041  100 100      100         96 98 7  97 100                        0  100                              5    0  0  0  042  100 -- -- 100            100               31 41 -- 0  23 5    -- -- -- --    20  29 100         38 98 15 0  100                        -- --47  100 -- -- 89 -- 31 47 -- 0  25 5    -- -- -- --    20  93 100         26 98 15 0  100                        -- --49  100 89 100         62 100               76 96 100                        0  0  5    0  P  0  P50  100 100      100         98 95 86 93 100                        0  46 5    0  P  0  P51  100 100      100         96 100               0  100                     100                        0  0  5    P  P  P  P52  100 100      100         95 94 93 81 100                        0  0  5    0  P  0  065  100 34 96 94 85 30 62 100                        0  0  5    0  0  0  067  100 -- -- 75 -- 0  68 -- 2  1  5    0  0  0  0    20  58 99 60 85 0  35 89 -- --94  100 86 61 96 98 78 36 100                        0  0  5    0  0  P  P99  100 100      100         89 83 98 61 100                        0  83 5    0  0  P  P100 100 100      100         96 83 95 80 100                        0  83 5    P  0  P  0101 100 100      100         94 83 0  80 100                        0  100                              5    0  0  P  0163 100 -- -- 95 -- 5  0  -- 0  0  5    -- -- -- --    20  0  81 58 23 5  0  99 -- --164 100 -- -- 84 -- 15 0  -- 8  0  5    -- -- -- --    20  82 100         57 88 5  0  100                        -- --170 100 -- -- 20 -- 10 0  -- 0  0  5    -- -- -- --    20  19 69 32 95 0  0  100                        -- --177 100 -- -- 26 -- 10 0  -- 0  0  5    -- -- -- --    20  82 26 50 46 0  0  100                        -- --208 100 84 37 83 76 4  61 97 0  74 5    0  0  0  0291 100 -- -- 81 -- 1  0  -- 24 78 5    -- -- -- --    20  32 26 6  83 1  0  73 -- --359 100 72 100         83 95 88 62 100                        0  0  5    0  0  0  0360 100 88 100         71 86 74 49 93 0  0  5    0  0  0  0361 100 -- -- 46 -- 1  0  -- 27 9  5    -- -- -- --    20  43 26 29 33 1  0  100                        -- --363 100 0  49 92 28 0  0  38 0  0  5    0  0  0  0447 100 -- 0  24 46 46 0  30 0  24 5    0  0  0  0448 100 -- 0  54 -- 0  42 16 0  0  5    -- -- -- --449 100 71 0  24 0  76 13 30 0  51 5    0  0  0  0450 100 -- 0  54 11 46 34 30 0  51 5    0  0  0  0451 100 16 100         72 0  0  0  0  0  0  5    0  0  0  0452 100 36 0  54 46 0  67 30 0  0  5    0  0  0  0453 100 55 32 75 94 0  0  100                        0  0  5    0  0  0  0454 100 0  0  0  22 0  0  0  0  0  5    -- -- -- --455 100 64 65 0  12 0  0  43 0  0  5    0  0  0  0456 100 82 0  58 53 98 0  96 9  0  5    0  0  0  0477 100 95 100         76 100               48 48 100                        0  0  5    P  P  P  P594 100 86 100         93 77 2  -- 100                        0  79 5    0  60 100                                            50596 100 -- -- 89 -- 0  0  -- 0  25 5    -- -- -- --    20  91 95 35 94 0  0  100                        -- --603 100 44 97 91 69 0  -- 95 0  0  5    0  0  0  0605 100 70 99 32 81 0  -- 100                        0  0  5    0  0  0  0608 100 87 100         98 98 4  81 100                        0  0  5    0  0  P  P618 100 100      100         98 89 0  -- 100                        0  0  5    0  80 80 P620 100 100      100         96 98 51 100                     100                        0  0  5    0  0  P  0622 100 100      100         84 99 0  100                     100                        0  26 5    0  0  P  0627 100 -- -- 38 -- 0  14 -- 0  61 5    -- -- -- --    20  31 70 19 81 0  0  99 -- --644 100 100      100         94 100               100                  100                     100                        23 0  5    0  0  P  P646 100 100      100         95 98 97 61 100                        0  99 5    100                                      0  0  0651 100 -- -- 42 -- 0  62 -- 0  46 5    0  0  0  0    20  67 0  7  67 0  0  100                        -- --656 100 93 100         88 97 0  50 100                        0  20 5    0  P  P  P657 100 62 100         81 98 49 97 100                        24 37 5    0  0  0  0661 100 -- -- 56 -- 0  70 -- 5  85 5    -- -- -- --    20  81 79 61 62 0  10 100                        -- --663 100 42 100         95 99 57 36 100                        0  39 5    -- -- -- --667 100 -- -- 4  -- 0  0  -- 0  10 5    0  0  0  0    20  13 14 7  39 0  0  0  -- --668 100 -- -- 76 -- 1  0  -- 22 31 5    -- -- -- --    20  65 17 31 31 1  0  100                        -- --669 100 100      100         90 100               96 100                     100                        0  0  5    0  0  P  0671 100 100      100         92 94 84 100                     100                        0  84 5    0  P  P  0675 100 -- -- 30 -- 0  62 -- 0  69 5    -- -- -- --    20  40 0  42 44 0  0  16 -- --685 100 -- -- 0  -- 0  29 -- -- -- 5    -- -- -- --    20  57 66 28 67 -- 15 100                        -- --721 100 73 89 95 94 18 100                     100                        0  0  5    P  P  P  P724 100 100      100         95 100               63 100                     100                        0  0  5    0  P  P  P726 100 -- -- -- -- 0  0  -- 0  38 5    0  20 0  0    20  75 0  23 81 0  0  100                        -- --815 100 40 98 0  62 2  -- 97 0  65 5    0  0  0  0905 100 -- -- 19 -- 0  37 -- 0  87 5    0  0  0  0    20  7  0  15 47 0  0  16 -- --1276    100 100      -- 96 100               1  97 100                        0  0  5    0  P  0  P    20  93 100         86 100               1  52 100                        -- --1276a    100 -- -- 53 -- 1  0  -- 16 22 5    -- -- -- --    20  42 26 33 88 1  0  100                        -- --1277    100 9  65 0  0  0  0  39 0  25 5    0  0  0  01277a    100 -- -- 36 -- 1  52 -- 8  31 5    -- -- -- --    20  58 74 24 95 1  0  100                        -- --1278    100 100      100         87 85 17 36 100                        0  16 5    0  0  0  01300    100 100      100         93 92 58 81 100                        0  0  5    0  0  0  01304    100 100      100         97 100               78 88 100                        0  18 5    0  0  0  01377    100 100      100         96 92 58 100                     100                        0  44 5    0  P  0  P1381    100 100      100         97 98 51 73 100                        0  78 5    0  50 0  01451    100 86 84 48 77 2  -- 93 0  79 5    0  0  0  01459    100 72 70 65 31 17 0  65 0  74 5    0  0  0  01468    100 40 0  0  77 2  -- 93 0  46 5    0  60 0  01469    100 68 84 81 77 2  -- 100                        24 89 5    0  80 70 01527    100 0  100         93 100               -- 35 100                        0  0  5    0  P  0  P__________________________________________________________________________ 
    
     TEST A 
     Seeds of crabgrass (Digitaria spp.), barnyardgrass (Echinochloa crusgalli), giant foxtail (Setaria faberii), wild oats (Avena fatua), cheatgrass (Bromus secalinus), velvetleaf (Abutilon theophrasti), morningglory (Ipomoea spp.), cocklebur (Xanthium pensylvanicum), sorghum, corn, soybean, sugarbeet, cotton, rice, wheat, barley and purple nutsedge (Cyperus rotundus) tubers were planted and treated preemergence with the test chemicals dissolved in a non-phytotoxic solvent. At the same time, these crop and weed species were treated with a soil/foliage application. At the time of treatment, the plants ranged in height from 2 to 18 cm. Treated plants and controls were maintained in a greenhouse for sixteen days, after which all species were compared to controls and visually rated for response to treatment. The ratings, summarized in Table A, are based on a numerical scale extending from 0=no injury, to 10=complete kill. The accompanying descriptive symbols have the following meanings: 
     C=chlorosis/necrosis; 
     B=burn; 
     D=defoliation; 
     E=emergence inhibition; 
     G=growth retardation; 
     H=formative effect; 
     U=unusual pigmentation; 
     X=auxillary simulation; 
     S=albinism; and 
     Y=abscised buds or flowers. 
     
         TABLE A   CMPD 52  CMPD 56          CMPD 52 (salt) CMPD 56 (salt) CMPD 57 CMPD 58 CMPD 59 CMPD 61 CMPD 66 CMPD 67 CMPD 99 CMPD 101 CMPD 106 RATE = KG/HA 0.1 0.4 0.4 0.4 0.4 0.4 0.4 0.4 0.4 0.4 0.4 0.4 0.4 0.4   POSTEMERGENCE COKER COTTON 2H 2H 0 7P,9G 4H 10P,9G 10P,9G 0 2H 10P,9G 10P,9G 5H 9G,10P 4G CULT MORNINGLRY 2C,4H 3C,6H 0 4C,9G 3C,7G 5C,9G 2C,3G 3C,5H 3C, 5C,9G 2C,2G 2C,4H 5C,9H 2C,8G COCKLEBUR 0 2C 0 3H,8G 2C 1H 2C,8H 0 1C 2C,5H 2C,5G 4C,7H 3C,6H 2C,2H PURPLE NUTSEDGE 0 --  0 0 5G 0 0 0 0 0 0 0 5G LARGE CRABGRASS 0 3C,6G 0 4G 0 9C 2C,8H 0 0 0 4G 9G 7G 2G BARNYARDGRASS 0 0 0 5G 0 7H 0 0 0 0 0 0 0 5H WILD OATS 0 2C,4G 0 0 0 0 0 0 0 0 0 0 0 0 ERA WHEAT 0 0 0 0 0 0 0 0 0 0 0 0 0 0 G4646 CORN 0 0 0 0 0 0 0 0 0 0 0 0 0 0 WILLMS SOYBEANS 0 1C 0 3C,8G 1C 4C,9G 4C,9G 1C,1H 3H 3C,4H 1C,4H 3C,5H 2C,4H 2C,5G RICE DRY SEEDED 0 1C 0 0 0 0 0 0 0 0 0 0 0 0 G522 SORGHUM 0 0 0 0 0 0 0 0 0 0 0 0 0 0 CHEAT GRASS   0 0  0 0 0 0 0 0 0 USH11 SUGARBEET 0 4G 0 5H,5I 2H 4H,5I 3H,7G 4H 3H 8H,5I 7H,5I 7H 6H 5G VELVETLEAF 3G 2C,5G 0 7G 2G 4C,9G 2C,8G 0 3C,5G 3G 2C,5G 8G 9H 3C,7G GIANT FOXTAIL 0 2C,5G 0 0 0 9G 0 0 0 0 0 0 0 0 KLAGES BARLEY 0 0 0 0 0 0 0 0 0 0 0 0 0 0 DOWNY BROME 0 0   0   0 0 PREEMERGENCE COKER COTTON -- 2G 0 5G 0 7G 8G 0 0 0 0 0 0 0 CULT MORNINGLRY 0 8H 0 4C,9G 0 4C,9G 8G 0 0 0 0 8H 2C,9H 0 COCKLEBUR 2G 2C,2G 0 2G 0 0 3G 0 0 0 0 0 0 0 PURPLE NUTSEDGE 0 0 0 5G 0 0 0 0 0 0 0 0 0 0 LARGE CRABGRASS 2C,7H 4C,9H 0 4C,9G 9G 4C,9G 9G 0 0 2C,9G 7G 2C,9G 2G 4C,9H BARNYARDGRASS 0 9C 5G 7C,9H 0 9C 4C,9H 0 0 0 3G 2G 2G 0 WILD OATS 0 0 0 0 0 0 0 0 0 0 0 0 0 0 ERA WHEAT 0 8G 0 0 0 2G 0 0 0 0 0 0 0 0 G4646 CORN 0 0 0 0 0 2G 3G 0 0 0 0 0 0 0 WILLMS SOYBEANS 0 0 0 7G 0 3C,9G 4G 0 0 0 1H 0 0 2G RICE DRY SEEDED 0 0 0 0 0 0 0 0 0 0 0 0 0 0 G522 SORGHUM 0 8G 0 7G 0 8G 7G 0 0 0 0 0 0 0 CHEAT GRASS   0 5G  9G 3G   0 3G 0 0 0 USH11 SUGARBEET 0 5H 0 6G 9H 7H 9G 0 0 5G 7G 3H 0 3H VELVETLEAF 0 4C,8H 0 4C,9G 0 5C,9G 5G 0 0 2G 0 0 0 0 GIANT FOXTAIL 3C,9H 9H 0 9H 4C,9G 9H 3C,9G 0 7G 3G 5G 2C,9H 7G 3C,9G KLAGES BARLEY 0 0 0 0 0 2G 0 0 0 0 0 0 0 3G DOWNY BROME 2G 3C,8G 0   0 0   CMPD 107 CMPD 108 CMPD 208 CMPD 594 CMPD 594 CMPD 596 CMPD 598 CMPD 603 CMPD 605 CMPD 611 CMPD 618 CMPD 620 CMPD 624 RATE = KG/HA 0.4 0.4 0.4 0.4 0.4 0.4 0.4 0.4 0.4 0.4 2 0.4 2 0.4   POSTEMERGENCE COKER COTTON 10P,8G 6H 0 4G 3G 0 8G 0 0 7G 8P,9G 3H 10P,9G 2H,9G CULT MORNINGLRY 5C,9G 3C,6G 2C,5H 6G 2C,2H 2C 0 3B 2B 0 0 2C,5G 3C,8G 2C,3H COCKLEBUR 3C,5G 2C,2H 2C 2C 0 1C 2C 1B 1B 1H 1H 2C,2H 3C,9G 2C,5H PURPLE NUTSEDGE 0 0 5G  0 0 3G 0 0 0 0 0 5G 0 LARGE CRABGRASS  0 0 0 2G 2G 0 2G 0 0 5G 8G 9G 2C,9G 9C BARNYARDGRASS 7H 0 0 0 0 0 0 0 0 2C 0 2H 3C,9H 6H WILD OATS 0 0 0 0 0 0 2G 0 0 0 0 0 0 0 ERA WHEAT 0 0 0 0 0 0 3G 0 0 0 0 0 0 2G G4646 CORN 0 0 0 0 2G 0 0 0 0 0 0 3C,3H 3C,7H 0 WILLMS SOYBEANS 5C,9G 2C,7G 2C,2H 2B,3H 2C,3H 2C 2C,2H 0 1C 2C,4H 2C,4G 3C,8G 4C,9G 3C,8H RICE DRY SEEDED 2C,5G 0 0 3G 0 0 0 0 0 0 0 2C,4G 2C,8G 0 G522 SORGHUM 0 0 0 0 0 0 0 0 0 0 0 2C 2C,3H 0 CHEAT GRASS   0 0 0 0 0 0 0 0 0 0 8G 0 USH11 SUGARBEET 0 3C,6G 6H 0 3G 1H 4G,5I 0 0 0 5H 3H 8H 7H,5I VELVETLEAF 3C,6G 2C,5G 8G 2C 0 1C 0 1B 0 0 2C,7G 3C,5H 2C,9G 1C GIANT FOXTAIL 0 0 0 0 2G 0 3G 0 0 0 8G 2C,7H 9G 2C,9G KLAGES BARLEY 0 0 0 0 0 0 0 0 0 0 0 0 0 0 DOWNY BROME 0 0 PREEMERGENCE COKER COTTON 3G 0 0 0 3G 3G 0 0 0 0 4G 9G 9G 0 CULT MORNINGLRY 5C,9G 3H 0 0 0 0 0 0 0 0 2H 2C,8G 9G 2G COCKLEBUR 0 0 0 0 0 2G 2G 0  0 0 3C,7G 2H 2G PURPLE NUTSEDGE 0 10E 0 0 0 10E 0 0 0 0 8E 5G 0 0 LARGE CRABGRASS 5C,9G 9G 0 9G 2U,9G 9H 3C,9G 0 3G 8G 8H 9H 9H 9H BARNYARDGRASS 9H 0 0 4C,8H 2C,8G 3C,7H 2G 0 0 2C,6G 5C,9H 2C,5H 7C,9H 8H WILD OATS 0 0 0 0 3G 0 0 0 0 0 0 0 0 0 ERA WHEAT 0 0 0 0 0 0 0 0 0 0 3G 0 0 0 G4646 CORN 0 0 0 0 2G 2G 0 0 0 0 3G 0 1H 0 WILLMS SOYBEANS 0 0 0 0 0 0 0 0 0 0 0 7G 8G 0 RICE DRY SEEDED 0 0 0 0 4G 0  0 0 0 2G 3G 2G 2G G522 SORGHUM 2H 0 0 0 3G 2C,9H  0 0 0 0 9G 9G 0 CHEAT GRASS   0 2G 3G 0  0 0 0 2G 0 2G 0 USH11 SUGARBEET 3H 0 2H 2G 4G 3G 7F 0 0 0 7G 8H 9H 8H VELVETLEAF 5G 0 0 4G 5G 2G  0 0 0 5G 6G 9H 8G GIANT FOXTAIL 3C,9G 8H 0 9G 3C,9G 9H  0 0 3C,8G 9H 9H 9H 9H KLAGES BARLEY 0 0 0 0 0 0 0 0 0 0 0 0 0 0 DOWNY BROME 0 0   CMPD 627 CMPD 644 CMPD 644 CMPD 646 CMPD 648 CMPD 651 CMPD 653 CMPD 656 CMPD 658 CMPD 659 CMPD 661 CMPD 669 CMPD 673 RATE = KG/HA 0.4 2 0.1 0.4 0.4 0.4 0.4 0.4 0.4 0.4 0.4 0.4 2 0.4   POSTEMERGENCE COKER COTTON 1C  5G 2C,7G 9G,10P 9P,9G 0 10P,9G 7G 0 0 1C,3H 3C,7H 10P,9G CULT MORNINGLRY 2C,6G 6C,9G 3C,3G 3C,5G 3C,8G 1C 2C 2C 2C,3H 0 3C,6G 1C 6C,9G 2C,1H COCKLEBUR 2C 5C,8H 0 2C 2C 2C 1C 2C,5G 2C 0 2C 1C 3C,7G 2C,3H PURPLE NUTSEDGE 0 8G,5X 0 0 0 0 0  2G 0 0 0 4G 0 LARGE CRABGRASS 0 3C,9G 0 0 6G 0 0 5C,9G 2G 0 0 0 2G 3C,3G BARNYARDGRASS 0 5C,9H 0 0 0 0 0 0 0 0 0 0 5C,9G 0 WILD OATS 0 3C,6G 0 0 0 0 0 0 0 0 0 0 2C,4G 0 ERA WHEAT 0 4C,8G 0 0 0 0 0 0 0 0 0 0 2G 0 G4646 CORN 0 3C,6H 0 0 0 0 2G 2G 0 0 0 0 0 0 WILLMS SOYBEANS 1H 9C 2C,2H 2C,5H 5C,8H 2C 1C 3C,7G 2C 0 3C 1H 5C,9G 1C,1H RICE DRY SEEDED 0 3C,8G 0 1C 0 0 0 0 0 0 0 0 0 0 G522 SORGHUM 0 3C,9H 0 0 0 0 0 0 0 0 0 0 2G 0 CHEAT GRASS 0 2C,8G  0 0 0 0 0 0 0 0 3G 0 USH11 SUGARBEET 2H 5G,5I 2G 7G 4H 4G,5I 1H 2C,7H 4H 0 0 4H 5G,5I 8H,5I VELVETLEAF 0 9G 3G 2C,6G 2C,3G 2C,5G 0 1C  8G 2C,5G 1C 6G 1C GIANT FOXTAIL 0 3C,9G 0 2C,3G 0 0 0 2C,7H 0 0 0 0 2G 9H KLAGES BARLEY 0 2C,9G 0 0 0 0 0 0 0 0 0 0 2G 0 DOWNY BROME   0 0 PREEMERGENCE COKER COTTON 0 9G 0 0 0 0 0 5G 0 0 3G 0 8G 0 CULT MORNINGLRY  0 9G 0 2C 0 0 0 2C,5G 0 0 1C 0 5C,9H 0 COCKLEBUR  3C,7G 0 0 0 0 0 2H 0 2G 0 0  0 PURPLE NUTSEDGE 0 10P 10E 10E 0 0 0 0 2G 6G 10E 0 3G 0 LARGE CRABGRASS 0 9H 3C,7H 5C,9H 9G 3C,8G 0 9C 5C,9H 9H 3C,9G 5G 9H 9H BARNYARDGRASS 0 9C 0 5C,9H 0 0 0 3C,9G 0 5G 2C,5G 0 9C 4H WILD OATS 0 4C,8G 0 2C,5G 0 0 0 0 0 0 0 0 2C 0 ERA WHEAT 0 9G 0 0 0 0 0 2G 0 0 0 0 0 2G G4646 CORN 0 2C,8H 0 0 0 2G 0 0 0 4G 0 0 2C,5H 2G WILLMS SOYBEANS 0 8G 0 0 3H 0 0 0 0 2G 0 0 8G 0 RICE DRY SEEDED 0 6G 0 0 0 0 0 0 0 0 0 0 0 0 G522 SORGHUM 0 3C,9G 0 4G 0 0 0 7G 0 0 0 0 9G 0 CHEAT GRASS 0 7G   0 2G 0 8G 0 0 0 0 0 3G USH11 SUGARBEET 0 9G 0 6H 5H 7H 0 8H 2H 0 0 5G 8G 6H VELVETLEAF 0 6C,9G 0 2C 2G 4G 0 5C,9G 0 0 7G 0 4C,8G 0 GIANT FOXTAIL 0 9H 3C,9H 5C,9H 9H 2C,9G 0 5C,9H 4C,9H 7H 3C,9H 3G 9H 2C,8G KLAGES BARLEY 0 3G 0 0 0 3G 0 0 0 0 0 0 0 2G DOWNY BROME   0 3C,5G   CMPD 675 CMPD 721 CMPD 724 CMPD 724 CMPD 726 CMPD 753 CMPD 754 CMPD 782 CMPD 784 CMPD 810 CMPD 811 CMPD 815 CMPD 863 RATE = KG/HA 0.4 0.4 0.4 0.4 0.4 0.4 0.4 0.4 0.4 0.4 0.4 0.4 2 0.4   POSTEMERGENCE COKER COTTON 0 5G 6G 10P,9G 4H 10P,9G 2H 10P,9G 10P,9G 0 10P,9G 9G,10P 2B 2C,6G CULT MORNINGLORY 1C 3C,6H 3C,5H 5C,9G 3C,7G 4C,9G 5C,9G 5C,9G 3H 2C,5G 5C,9G 3C,9H 0 1C,2G COCKLEBUR 0 2C 3C,4H 3C,9H 1C,2H 2C,6G 2C,3H 8G 2H 8G 3H,8G 2C,4H 0 2C PURPLE NUTSEDGE 0 0 2C,8H 0 0 0 0 0 0  0 0 0 0 LARGE CRABGRASS 0 0 9G 5G 0 4C,9G 0 5C,9G 6H 5G 9C 0 1B 0 BARNYARDGRASS 0 0 2C,3H 7G 0 5H 0 7H 0 2G 3C,9G 0 1B 0 WILD OATS 0 0 0 0 0 0 0 0 0 0 0 0 0 0 ERA WHEAT 0 0 0 2G 0 0 0 0 0 0 0 0 0 0 G4646 CORN 0 0 0 0 2G 0 0 0 0 0 0 0 1B 0 WILLMS SOYBEANS 1C 2C 4C,8H 3C,9G 2H 9C 2C,3H 8G 2C,5H 5G 3C,9G 0 2B 2C RICE DRY SEEDED 0 0 5G 0 0 0 0 0 0 0 0 0 0 0 G522 SORGHUM 0 0 0 0 0 2G 0 0 0 0 0 0 0 0 CHEAT GRASS 0 0 0 0 0 0  0 0 0 0 0 0 0 USH11 SUGARBEET 1C 3H 7H 3H 3H 8H 7G 7H,5I 7H 4G 6H,5I 0 1B 0 VELVETLEAF 0 6G 9H 3C,9G 0 3C,8G 3G 8G 2H 8G 4C,9G 0 2B 2C GIANT FOXTAIL 0 0 9G 9G 5G 2C,9G 0 7G 2G 2G 9G 0 1B 0 KLAGES BARLEY 0 0 0 0 0 0 0 0 0 0 0 0 0 0 DOWNY BROME       0 PREEMERGENCE COKER COTTON 0 0 0 8G 0 3G 0 0 0 0 9G 0 0 5G CULT MORNINGLRY 0 3H 2C,8H 9C 0 9G 0 3C,9H 1H 0 9C 0 0 0 COCKLEBUR  0 0 0 2G 3H 0 0 0 2G 0   2G PURPLE NUTSEDGE 0 0 0 0 0 9G 0 0 5G 0 10E 0 0 4G LARGE CRABGRASS 0 7G 2C,9H 4C,9H 7G 9G 8G 3C,9G 9H 9H 5C,9H 9G 0 4G BARNYARDGRASS 0 0 5C,9H 5C,9H 3C,6G 8G 2H 2C,9H 0 4C,9H 7C,9H 0 0 3G WILD OATS 0 0 0 0 0 0 0 0 0 2G 0 0 0 2G ERA WHEAT 0 0 0 0 0 0 0 0 0 2G 0 0 0 0 G4646 CORN 0 0 0 0 2G 0 0 0 0 0 2G 0 0 0 WILLMS SOYBEANS 0 0 0 6G 0 3G 0 3G 0 0 7G 0 0 0 RICE DRY SEEDED 0 0 0 0 0 0 0 0 0 0 0 0 0 0 G522 SORGHUM 0 0 0 6G 0 5G 0 6G 2G 0 8G 0 0 0 CHEAT GRASS 0 0 0 8G 0 0  0 0 3G 5G 0 0 2G USH11 SUGARBEET 0 2C,3H 5H 8G 2H 8H 3G 9G 5G 9G 8G 0 0 0 VELVETLEAF 0 2G 9G 4C,9G 0 4G 0 2C,8G 4G 3G 2C,9G 3G 0 0 GIANT FOXTAIL 0 7G 3C,9H 9H 2C,9H 3C,9G 7G 9H 3G 9H 9H 2G 0 8G KLAGES BARLEY 0 0 0 0 0 0 0 0 0 0 2G 0 0 0 DOWNY BROME       0 CMPD 1276        CMPD 879 CMPD 905 CMPD 1276 (salt) CMPD 1276A CMPD 2004 CMPD 1278 CMPD 2003 CMPD 2016 CMPD 1377 CMPD 1381 RATE = KG/HA 0.4 0.4 0.4 0.4 0.4 0.4 0.4 0.4 0.4 0.4 2 0.4 2   POSTEMERGENCE COKER COTTON 0 0 4H 9G,10P 7G 3H,6G 0 10P,9G 7G 9G,10P 9G,10P 3G 10P,9G CULT MORNINGLRY 1C,2H 2C 2C,4H 2C,3G 1C 2C,3G 1C 5C,9G 2H 2C,6H 4C,9H 3C,5G 2C,8H COCKLEBUR 1C 0 2C 3C 1C 2C,7G 1C 5H 4H 2C,3H 4C,9H 2C 2C,7H PURPLE NUTSEDGE 0 0 0 0  0 0 0 0 -- 4G 0 2C,5G LARGE CRABGRASS 3G 0 0 0 0 4G 4G 3C,5G 9H 0 4C,9G 2G 4C,9G BARNYARDGRASS 0 0 0 0 0 1C 0 2G 5H 2G 5C,9H 2H 9H WILD OATS 0 0 0 0 0 0 0 0 0 0 0 0 2G ERA WHEAT 0 0 0 0 0 0 0 0 0 0 0 0 2G G4646 CORN 0 0 0 0 0 0 0 0 0 0 0 0 3G WILLMS SOYBEANS 2H,5G 0 2C,6H 3C 2H,6G 1C,1H 0 3C,5G 5C,9G 3C,5H 3C,6H 2C,4G 2C,8G RICE DRY SEEDED 2G 0 0 0 0 0 0 0 0 0 0 0 8G G522 SORGHUM 0 0 0 0 2G 0 0 0 2G 0 0 0 9H CHEAT GRASS 0 0 0 0 0 0 0 0 0 0 2G -- 2G USH11 SUGARBEET 3G 0 2H 0 3H 1H 1H 7H,5I 8H 6H,5I 7H,5I 5G 9H VELVETLEAF 2G 0 8G 2C,4G 2C 0 0 3C,7G 7H 2C,3H 3C,7H 0 9G GIANT FOXTAIL 0 0 0 0 0 3G 0 0 9H 0 3C,9H 0 9G KLAGES BARLEY 0 0 0 0 0 0 0 0 0 0 0 0 2G DOWNY BROME   0 -- PREEMERGENCE COKER COTTON 0 0 0 0 0 0 0 0 2G 0 7G 0 8G CULT MORNINGLRY 0 0 0 1C,3G 0 0 0 0 2H 2C 2C,3G 0 7H COCKLEBUR 0  0 0 0 0 0 0 0 0 2G 0 3G PURPLE NUTSEDGE 8G 0 0 8G 10E 0 0 0 0 0 9G 0 0 LARGE CRABGRASS 9H 0 4C,9H 7G 0 5C,9G 0 7G 9H 4C,8H 5C,9H 5C,9G 3C,9G BARNYARDG RASS 4C,8H 0 4C,8H 0 0 3C,8H 0 2G 3G 2G 10C 3H 5C,9H WILD OATS 0 0 0 0 0 0 0 0 0 0 0 0 0 ERA WHEAT 0 0 0 0 0 0 0 0 0 0 0 0 0 G4646 CORN 2G 0 0 0 0 2G 0 0 0 0 0 0 3G WILLMS SOYBEANS 2G 0 0 0 0 0 0 0 0 0 5G 0 9G RICE DRY SEEDED 0 0 0 2G 0 0 0 0 0 0 0 0 4G G522 SORGHUM 0 0 0 0 0 0 0 0 0 0 2C,6G 0 7G CHEAT GRASS 2G 0 0 0 0 0 0 0 0 0 0 -- 0 USH11 SUGARBEET 5H 0 2H 7G 6G 7H 0 3H 5G 2C,6H 8G,5I 2H 8H VELVETLEAF 4G 0 0 4G 8G 3G 0 5G 5G 3G 7G 3G 8G GIANT FOXTAIL 9H 0 4C,9H 2C,9G 0 3C,9H 2G 8G 9H 3C,9H 4C,9H 4C,9H 9H KLAGES BARLEY 0 0 0 0 0 0 0 0 0 0 0 0 0 DOWNY BROME 0 --   CMPD 1304 CMPD 1 CMPD 4 CMPD 9 CMPD 11 CMPD 13 CMPD 15 CMPD 16 CMPD 17 C MPD 18 CMPD 23 CMPD 33 CMPD 34 RATE = KG/HA 0.4 2 0.4 0.4 0.1 0.4 2 0.4 0.4 0.4 0.4 0.4 0.4 0.4 0.4   POSTEMERGENCE COKER COTTON 5H 10P,9G 3H 3C,9H 3H 3H 10P,9G 6H 7G 8G 3H 7G,5I 2H 10P,9G 10P,8G CULT MORNINGLRY 3C,7G 2C,7G 1C,1H 4C,8H 3C,4H 3C,6G 4C,9G 4C,8G 2C,4H 4C,9G 3C,4G 2C 2C,3H 2C,5G 3C,10P COCKLEBUR 2C,4G 8H 1C,3G 3C,8H 0 3C,6G 3C,9G 3C,3H 2C 2C,6G 2C,5G 2C,3G 1C,1H 3C,4H 2C,2H PURPLE NUTSEDGE 0 8G 0 5G 0 9G 7G 0 0 0 0 0 0 0 0 LARGE CRABGRASS 3C,7G 3C,9G 0 9G 0 3G 9C 0 0 8G  3C,7G 3G 5C,9G 3G BARNYARDGRAS S 5H 9H 0 2C,8H 0 0 5C,9G 0 3G 0 0 9H 0 0 0 WILD OATS 0 2G 0 0 0 0 7G 0 0 0 0 0 0 0 0 ERA WHEAT 0 4G 0 0 0 0 8G 0 0 0 0 0 0 0 0 G4646 CORN 0 3G 2G 2G 0 0 7H 0 0 0 0 0 0 2G 0 WILLMS SOYBEANS 2C,5G 2C,6G 2C,3H 4C,8G 1C,1H 2C,4H 4C,9G 3C,5G 3C,5H 2C,2H 1C,2H 3C,5G 1C,1H 4C,9G 4C,9G RICE DRY SEEDED 0 7G 0 5G 0 1C 3C,7G 0 0 2C 1C 0 0 0 2G G522 SORGHUM 0 7G 0 5G 0 0 3C,8H 2G 0 0 0 0 0 0 0 CHEAT GRASS -- 5G 0 5G   7G  0 0 0 0 0 0 USH11 SUGARBEET 2H 7H,5I 8G 6H 3G 3G 9H,5I 7G 5H 2G 7H 3G,5I 4H 8H,5I 7H VELVETLEAF 0 9G 0 2C,8H -- 4G 3C,9G 2C 6G 6G 0 2C,5G 0 3C,8G 5C,8G GIANT FOXTAIL 0 9H 0 9G 0 2C,2G 9G 3G 0 7G 3G 5G 2G 9G 0 KLAGES BARLEY 0 3G 0 0 0 0 5G 0 0 0 0 0 0 0 0 DOWNY BROME 0 --   0 0  0       3G PREEMERGENCE COKER COTTON 0 7G 0 8G 0 5H 9G 0 0 5G 0 0 0 8G 0 CULT MORNINGLRY 0 7G 0 9H 0 1C 9G 0 0 0 0 1H 0 7G 6G COCKLEBUR 0 0 0 0 0 0 2C,8G 0 0 0 0 0 0 2G 0 PURPLE NUTSEDGE 0 3G 5G 0 0 8G 10E 0 9G 10E 10E 7G 0 0 0 LARGE CRABGRASS 4C,9H 4C,9G 4C,9G 9C 3C,7H 4C,9H 9H 5C,9G 3C,9H 8G 9G 10H 9H 8G 3C,9G BARNYARDGRASS 0 5C,9H 1C 10C 4C,6H 9C 5C,9H 3C,7G 0 5G 3G 5C,9H 3C,6G 2C,8H 5G WILD OATS 0 2G 0 0 0 0 8G 0 0 0 0 0 0 0 0 ERA WHEAT 0 0 2G 0 0 2G 2C,9G 0 0 0 0 7G 0 0 0 G4646 CORN 0 5G 0 0 0 2C,2H 3C,8H 3G 0 2G 0 2G 0 0 0 WILLMS SOYBEANS 0 7G 2G 0 0 3C,7H 9G 0 0 0 0 0 0 4G 0 RICE DRY SEEDED 0 0 3G 0 0 0 0 0 0 2G 0 0 0 2G 0 G522 SORGHUM 3G 9G 0 9H 0 2C,9G 9H 2H 0 0 0 9G 0 5G 1H CHEAT GRASS -- 6G 0 0   3C,8G  0 0 0 8G 4G 0 USH11 SUGARBEET 0 8H 4H 8H 3H 6H 9H 7H 0 6G 0 7H 3H 7G 5H VELVETLEAF 5G 7G 5G 7H 0 5C,9H 9G 9C 6G 5G 2G 7G 3G 2G 7G GIANT FOXTAIL 3C,9H 9H 3C,9H 3C,9H 4C,9H 4C,9H 9H 2C,9G 0 9H 6G 9H 5C,9H 9H 3C,9H KLAGES BARLEY 0 0 0 0 0 0 4G 0 0 0 0 0 0 0 0 DOWNY BROME 0 --   0 2C,7G  4G 0         CMPD 35 CMPD 35 CMPD 35 CMPD 35      CMPD 34 CMPD 34 CMPD 35 (salt) (salt) (salt) (salt) CMPD 39 CMPD 42 CMPD 47 CMPD 51 CMPD 52 RATE =  KG/HA 0.4 0.4 0.4 2 2 0.4 0.4 0.4 0.4 0.4 0.4 2 2  POSTEMERGENCE COKER COTTON 8P,8G 4G 10P,9G 10P,9G 10P,9G 3H 0 9P,8G 8G,10P 1C 10P,8G 1C,6H 3H,8G CULT MORNINGLRY 5C,9G 010P,9G 4C,9G 5C,9G 3C,8G 0 2C,2H 2C 2C 1C 5G 5C,9G COCKLEBUR 2C,2H 2C,3H 2C,5G 3C,8G 4C,9H 2C,1H 0 2C,2H 2C 3C 1C 2C,7H 3C,9H PURPLE NUTSEDGE 0 0 2G 8G 8G 0 0 0 0 0 0 0 LARGE CRABGRASS 0 5G 2C,9G 3C,9G 3C,9G 0 0 0 0 0 0 2C,9G 3C,9G BARNYARDGRASS 0 5H 2C,8H 4C,9H 5C,9G 0 0 5H 0 0 0 2C,7G 5C,9G WILD OATS 0 0 0 5C,9Z 0 0 0 0 0 0 0 2C,2G 2C,4G ERA WHEAT 0 0 3C,8G 0 0 0 0 0 0 0 0 2C,3G 2C,6G G4646 CORN 0 0 5G 3C,7H 3C,7H 2H 0 2G 0 0 2G 2C,6H 2C,6G WILLMS SOYBEANS 2C,3H 4C,7G 9H 3C,9G 4C,9G 3C,9G 2G 9G,5I 2C 1H 2C,2H 3C,7H 4C,9G RICE DRY SEEDED 9H 0 1C 3C,9G 4G 0 0 0 0 0 0 2C,5G 2C,6G G522 SORGHUM 0 0 0 3C,9H 7G 0 0 0 0 0 0 0 9H CHEAT GRASS   0 5G 4G   0 0 0 0 5G 2C,6G USH11 SUGARBEET 3G 6G 5H 2C,8H 3H,7G 7G 2G 4H 4H 3H 0 7G 3H,7G VELVETLEAF 3C,8G 5C,9G 4C,8G 4C,9G 7C,9G 3C,5G 0 3C,8H 4H 5C 0 4G 7C,9G GIANT FOXTAIL 0 0 8H 9G 3C,9G 2G 0 0 0 2G 0 2C,7G 1C,9G KLAGES BARLEY 0 0 0 1C 6G 0 0 0 0 0 0 0 6G DOWNY BROME 0 0    0 0 PREEMERGENCE COKER COTTON 0 0 6G 8H 9G  0 8G 0 0 0 5G 9G CULT MORNINGLRY 8G 2C,8G 8H 9H 3C,9H 8G 0 6G 0 0 0 9H 5H,9G COCKLEBUR 0 0 1H 2H 0 0 0 0 0  0 1C,2G PURPLE NUTSEDGE 0 0 0 0 3G 0 0 0 0 0 0 0 0 LARGE CRABGRASS 4C,9G 4C,9G 9H 10E 10H 3C,9G 0 3C,9G 6G 2C,9G 9G 10H BARNYARDGRASS 5H 3C,8G 6C,9H 7C,9H 9H 7H 0 3C,9G 2G 0 1H 3C,9H WILD OATS 0 0 0 7G 8G 0 0 2G 0 2G 0 2G 2C,8G ERA WHEAT 0 0 0 8G 5G 0 0 0 0 0 0 0 4C,9G G4646 CORN 0 2G 0 2C,3H 3G 0 0 0 0 0 3G 0 3C,8H WILLMS SOYBEANS 0 0 2G 7G 2C,9G 0 0 9G 0 0 0 0 9G,5I RICE DRY SEEDED 0 0 0 1C 0 0 0 4G 0 0 0 0 8G G522 SORGHUM 0 0 7G 9H 2C,9G 0 0 5G 0 0 0 2C,9G 9G CHEAT GRASS   0 8G 8G   5G 0 0 0 3G 9G USH11 SUGARBEET 2H 4H 5H 9H 9G 3H 0 5H 2H 5H 4H 9H 9G VELVETLEAF 5G 5C,8G 8H 9H 9G 5C,9G 0 7G 0 0 0 9H 9G GIANT FOXTAIL 3C,9H 3C,9G 9H 9H 9H 9H 0 3C,9G 6G 3C,9G 3C,9H 3C,9H 10H KLAGES BARLEY 0 0 0 0 0 0 0 0 0 0 0 0 7G DOWNY BROME 0 3G    0 0 
    
     TEST B 
     Postemergence 
     Three round pans (25 cm diameter by 12.5 cm deep) were filled with Sassafras sandy loam soil. One pan was planted with nutsedge (Cyperus rotundus) tubers, crabgrass (Digitaria sanguinalis), sicklepod (Cassia obtusifolia), jimsonweed (Datura stramonium), velvetleaf (Abutilon theophrasti), lambsquarters (Chenopodium album), rice (Oryza sativa), and teaweed (Sida spinosa). The second pot was planted with green foxtail (Setaria viridis), cocklebur (Xanthium pensylvanicum), morningglory (Ipomoea hederacea), cotton (Gossypium hirsutum), johnsongrass (Sorghum halepense), barnyardgrass (Echinochloa crusgalli), corn (Zea mays), soybean (Glycine max), and giant foxtail (Setaria faberi). The third pot was planted with wheat (Triticum aestivum), barley (Hordeum vulgare), wild buckwheat (Polygonum convolvulus L.), cheatgrass (Bromus secalinus L.), sugarbeet (Beta vulgaris), wild oat (Avena fatua L.), common chickweed (Stellaria media), blackgrass (Alopecurus myosuroides), and rape (Brassica napus). The plants were grown for approximately fourteen days, then sprayed postemergence with the chemicals dissolved in a nonphytotoxic solvent. 
     Premergence 
     Three round pans (25 cm diameter by 12.5 cm deep) were filled with Sassafras sandy loam soil. One pan was planted with nutsedge tubers, crabgrass, sicklepod, jimsonweed, velvetleaf, lambsquarters, rice and teaweed. The second pot was planted with green foxtail, cocklebur, morningglory cotton, johnsongrass, barnyardgrass, corn, soybean, and giant foxtail. The third pot was planted with wheat, barley, wild buckwheat, cheatgrass, sugarbeet, wild oat, viola, blackgrass, and rape. The thee pans were sprayed preemergence with the chemicals dissolved in a nonphytotoxic solvent. 
     Treated plants and controls were maintained in the greenhouse for approximately 24 days, then all rated plants were compared to controls and visually rated for plant response. 
     Response ratings are based on a scale of 0 to 100 where 0=no effect, and 100=complete control. A dash (-) response means no test. 
     Response ratings are contained in Table B. 
     
         TABLE B  CMPD 51 CMPD 669 CMPD 35 CMPD 52 CMPD 18 CMPD 35 CMPD 33 RATE = G/HA 0250 0125 0062 2000 1000 0500 0250 0500 0250 2000 1000 0250 0062 2000 1000 0250 0062 0500 0250 0250 0500 0250 0125   POST GIANT FOXTAIL -- 0 0 -- 50 30 0 100 90 -- 80 70 30 -- 70 50 30 30 0 80 30 0 0 VELVETLEAF 30 0 0 80 50 30 0 100 70 100 90 70 50 90 70 50 30 80 50 70 90 70 60 USH11 SUGARBEET -- 30 0 -- 80 70 50 70 50 -- 70 60 50 -- 70 50 30 60 50 60 90 80 70 LARGE CRABGRASS 0 0 0 80 70 50 30 100 50 100 100 90 30 100 90 90 50 30 20 80 70 60 50 PRICKLY SIDA 30 0 0 90 70 50 30 100 90 100 90 70 50 90 80 70 50 70 50 80 70 60 50 JIMSONWEED 0 0 0 60 40 20 0 60 20 90 70 50 0 90 70 50 30 40 0 50 90 70 50 RICE DRY SEEDED 0 0 0 0 0 0 0 30 10 60 30 0 0 60 40 0 0 40 30 0 0 0 0 COCKLEBUR 30 0 0 60 30 0 0 30 -- 90 70 50 30 90 60 30 0 40 20 30 30 20 0 COKER COTTON 20 0 0 70 50 30 0 90 70 50 40 30 20 50 40 30 0 60 40 90 30 30 30 WILLMS SOYBEANS -- 0 0 -- 40 0 0 80 60 -- 80 60 20 -- 30 0 0 30 30 30 60 50 40 BARNYARDGRASS 0 0 0 70 50 30 0 100 80 80 60 30 0 90 60 30 0 10 10 90 0 0 0 WILD OATS -- 0 0 -- 0 0 0 50 0 -- 30 0 0 -- 30 0 0 30 0 0 30 0 0 IVY MORNINGLORY 30 0 0 100 70 50 30 20 0 70 60 50 30 90 70 50 30 30 20 70 80 70 50 ERA WHEAT -- 0 0 -- 0 0 0 10 0 -- 0 0 0 -- 50 30 0 0 0 0 0 0 0 SICKLEPOD 0 0 0 80 30 0 0 50 30 90 70 50 30 70 40 30 0 40 20 20 50 30 20 JOHNSONGRASS 0 0 0 30 0 0 0 100 100 90 70 50 30 90 70 50 0 40 0 90 0 0 0 PURPLE NUTSEDGE 0 0 0 30 0 0 0 80 -- 30 0 0 0 50 30 0 0 30 0 0 0 0 0 G4646 CORN -- 0 0 -- 0 0 0 0 0 -- 40 0 0 -- 40 0 0 0 0 0 0 0 0 WILD BUCKWHEAT -- 0 0 -- 70 60 50 -- 0 -- 70 50 30 -- 70 50 30 40 -- 50 60 30 0 BLACKGRASS -- 0 0 -- 50 30 0 90 60 -- 50 30 0 -- 70 50 30 40 0 40 30 0 0 ALTEX RAPE -- 0 0 -- 50 30 0 80 60 -- 80 50 30 -- 50 30 0 100 80 50 70 50 30 KLAGES BARLEY -- 0 0 -- 0 0 0 0 0 -- 0 0 0 -- 30 0 0 10 0 0 0 0 0 GREEN FOXTAIL 30 0 0 80 50 30 0 100 90 90 80 60 30 90 70 50 30 40 0 80 30 0 0 CHEAT GRASS -- 0 0 -- 0 0 0   -- 0 0 0 -- 50 30 0 30 10  0 0 0 FIELD VIOLET -- 0 0 -- 0 0 0   -- 0 0 0 -- 50 30 0    90 60 30 LAMBSQUART ER 70 60 50 90 80 70 60 100 80 100 100 70 50 90 80 70 50 100 50 60 80 70 50 CHICKWEED SPP.        80 20         50 0 0 DOWNY BROME        40 20    0   CMPD 35 CMPD 1381 CMPD 1304 CMPD 810 CMPD 9 CMPD 107 CMPD 13 RATE = G/HA 0500 0250 0125 0062 0250 0125 0062 0250 0125 0062 0500 0250 0125 0062 0500 0250 0125 0500 0250 0125 0250 0125   POST GIANT FOXTAIL 0 0 0 -- 60 30 0 0 0 0 80 20 0 0 80 50 30 60 20 0 20 0 VELVETLEAF 90 70 50 30 0 0 0 100 70 30 60 30 20 0 70 40 -- 80 80 70 70 60 USH11 SUGARBEET 50 30 0 -- 70 50 30 30 0 0 20 20 0 -- 90 50 40 90 90 80 80 40 LARGE CRABGRASS 70 60 50 30 0 0 0 0 0 0 40 20 0 0 30 20 0 30 30 -- 0 0 PRICKLY SIDA 90 60 30 0 0 0 0 50 30 0 30 20 0 0 70 60 30 100 90 80 60 40 JIMSONWEED 30 20 0 0 60 50 30 60 30 0 30 20 0 0 50 30 30 90 50 30 40 30 RICE DRY SEEDED 0 0 0 0 0 0 0 0 0 0 30 0 0 0 30 0 0 10 0 0 0 0 COCKLEBUR 30 0 0 0 50 30 0 50 30 0 30 20 0 0 40 40 30 50 40 20 30 0 COKER COTTON 60 40 30 0 50 30 0 50 30 0 30 20 10 10 80 60 30 90 70 60 90 80 WILLMS SOYBEANS 60 40 30 -- 30 0 0 30 0 0 80 30 0 0 30 20 0 -- 60 0 40 0 BARNYARDGRASS 0 0 0 0 0 0 0 0 0 0 30 20 0 0 100 90 30 100 80 70 20 0 WILD OATS 0 0 0 -- 0 0 0 0 0 0 30 20 0 -- 30 20 10 20 20 -- 30 0 IVY MORNINGLORY 50 30 0 0 50 30 0 30 0 0 0 0 0 0 50 -- 0 100 90 60 70 40 ERA WHEAT 0 0 0 -- 0 0 0 0 0 0 20 0 0 0 0 0 0 0 0 0 10 0 SICKLEPOD 50 30 0 0 30 0 0 50 30 0 20 0 0 0 70 60 60 90 40 20 40 20 JOHNSONGRASS 50 30 0 0 30 0 0 0 0 0 20 0 0 0 50 30 0 0 0 0 0 0 PURPLE NUTSEDGE 60 30 0 0 30 0 0 70 50 30 0 0 0 0 -- 0 0 70 70 0 0 0 G4646 CORN 0 0 0 -- 0 0 0 0 0 0 30 20 0 0 0 0 0 0 0 0 0 0 WILD BUCKWHEAT 80 50 30 -- 50 30 0 60 30 0 60 20 0 -- 60 40 30 90 70 70 50 30 BLACKGRASS 50 30 0 -- 70 50 30 30 0 0 80 30 20 -- 70 10 0 70 40 0 80 30 ALTEX RAPE 30 0 0 -- 30 0 0 0 0 0 80 30 20 -- 60 40 0 70 60 60 30 0 KLAGES BARLEY 0 0 0 -- 0 0 0 0 0 0 30 20 0 -- 0 0 0 0 0 0 0 0 GREEN FOXTAIL 50 30 0 0 30 0 0 0 0 0 30 20 0 0 100 70 30 80 40 30 40 0 CHEAT GRASS 0 0 0 -- 0 0 0    0 0 0 -- FIELD VIOLET LAMBSQUARTER 50 30 0 0 0 0 0 80 50 0 80 70 30 0 -- 90 50 80 80 60 50 -- CHICKWEED SPP. 60 30 0 -- 0 0 0 60 30 0 80 20 0 -- 70 70 30 80 50 40 50 0 DOWNY BROME        0 0 0     0 0 0 0 0 0 0 0   CMPD 669 CMPD 35 CMPD 35 CMPD 52 CMPD 18 CMPD 35 CMPD 33 RATE =  G/HA 2000 1000 0500 0250 0500 0125 2000 1000 0250 0062 2000 1000 0250 0062 0500 0250 0125 0062 0250 0125 0062 0500 0250 0125   PRE GIANT FOXTAIL 100 100 100 100 100 100 100 100 100 90 100 100 90 60 100 100 90 30 100 100 100 100 90 80 VELVETLEAF 50 30 0 0 100 90 90 80 70 60 90 70 50 30 70 20 -- -- -- 90 30 90 80 70 USH11 SUGARBEET 70 50 30 0 90 20 60 40 30 0 80 50 30 0 50 30 20 -- 50 20 0 80 50 30 LARGE CRABGRASS 100 100 90 80 100 100 100 100 100 100 100 100 100 80 100 100 100 50 100 100 60 90 70 50 PRICKLY SIDA 90 70 50 30 100 100 90 80 70 60 90 80 80 70 90 90 80 50 -- 70 60 60 30 0 JIMSONWEED 70 50 40 30 70 50 100 90 80 60 100 100 70 50 70 20 0 0 0 0 0 70 50 30 RICE DRY SEEDED 0 0 0 0 10 0 0 0 0 0 50 30 0 0 10 0 0 0 30 10 0 0 0 0 COCKLEBUR 40 20 0 0 20 0 50 40 30 0 100 100 50 30 20 0 0 0 0 -- 0 30 0 0 COKER COTTON 0 0 0 0 100 20 80 70 60 30 80 60 20 0 10 0 0 -- 50 20 0 30 0 0 WILLMS SOYBEANS 0 0 0 0 10 0 90 80 30 0 80 60 0 0 10 0 0 0 40 10 0 0 0 0 BARNYARDGRASS 100 100 50 30 100 60 100 100 100 60 100 100 80 30 100 60 20 0 80 30 10 100 90 80 WILD OATS 0 0 0 0 40 20 0 0 0 0 30 20 0 0 30 0 -- -- 10 0 0 0 0 0 IVY MORNINGLORY 40 0 0 0 0 0 80 60 40 0 80 60 40 0 40 30 30 0 50 40 40 60 40 20 ERA WHEAT 0 0 0 0 20 0 0 0 0 0 50 30 0 0 10 0 0 0 0 -- 0 0 0 0 SICKLEPOD 30 0 0 0 50 0 90 70 30 0 90 60 30 0 100 50 30 0 90 40 30 50 30 0 JOHNSONGRASS 90 80 50 30 100 50 100 100 90 70 100 90 80 50 90 60 30 0 70 10 0 50 30 0 PURPLE NUTSEDGE 0 0 0 0 50 0 0 0 0 0 70 30 0 0     0 0 0 0 0 0 G4646 CORN 0 0 0 0 40 10 60 40 20 0 60 30 0 0 10 10 10 0 0 0 0 0 0 0 WILD BUCKWHEAT 70 50 30 0 100 30 80 70 50 30 80 50 30 0 50 30 30 0 40 0 -- 0 0 0 BLACKGRASS 70 50 30 0 100 80 90 80 60 30 90 70 50 30 90 80 80 30 50 -- 10 30 0 0 ALTEX RAPE 70 50 30 0 80 40 90 70 50 30 70 40 20 0 30 20 20 -- 40 40 30 90 80 70 KLAGES BARLEY 0 0 0 0 0 0 0 0 0 0 30 20 0 0 30 30 20 10 10 0 0 0 0 0 GREEN FOXTAIL 100 100 100 100 100 100 100 100 100 100 100 100 90 70 100 100 100 30 100 100 70 100 90 80 CHEAT GRASS 30 0 0 0 100 90 60 30 0 0 70 50 30 0 40 20 20 20    0 0 0 FIELD VIOLET 80 30 0 0 40 -- 80 70 50 30 100 90 30 0        70 50 30 LAMBSQUARTER 100 90 70 50 80 40 100 100 90 80 100 100 90 80 100 90 80 60 100 70 60 100 100 100 CHICKWEED SPP.               50 20 -- -- 40 30 0 DOWNY BROME      30 10 0   CMPD 35 CMPD 1381 CMPD 1304 CMPD 810 CMPD 9 CMPD 107 CMPD 13 RATE = G/HA 0500 0250 0125 0062 0250 0125 0062 0250 0125 0062 0500 0250 0125 0062 0500 0250 0125 0062 0500 0250 0125 0062 0250 0125 0062   PRE GIANT FOXTAIL 100 100 100 90 100 100 90 100 100 70     100 100 100 40 100 100 90 70 100 90 40 VELVETLEAF 90 80 60 50 0 0 0 30 0 0 50 40 20 0 100 70 40 20 80 40 30 20 40 20 0 USH11 SUGARBEET 70 50 40 0 90 70 50 50 30 0 40 30 30 20 90 70 60 40 90 80 60 10 90 80 50 LARGE CRABGRASS 100 100 100 100 100 100 100 100 90 80 100 90 90 20 100 100 100 100 100 100 100 100 100 100 100 PRICKLY SIDA 70 60 60 50 30 0 0 70 50 30 60 50 30 20 90 50 10 0 80 80 70 0 90 60 40 JIMSONWEED 40 40 20 0 50 30 0 30 0 0 50 40 30 30 80 50 30 30 50 40 20 0 50 30 0 RICE DRY SEEDED 10 10 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 COCKLEBUR 30 30 0 0 50 30 0 50 30 0 30 20 0 0 30 0 0 0 10 0 0 0 20 0 0 COKER COTTON 60 10 0 0 30 30 30 0 0 0 0 0 0 0 30 10 -- 0 10 0 0 0 0 0 0 WILLMS SOYBEANS 10 10 0 0 0 0 0 0 0 0 20 0 0 0 10 0 0 0 0 0 0 0 0 0 0 BARNYARDGRASS 100 90 40 30 80 50 30 70 30 0 100 90 70 40 100 100 30 0 100 90 40 0 90 40 0 WILD OATS 40 30 20 0 50 30 0 50 30 0 20 0 0 0 0 0 0 0 30 0 0 0 0 0 0 IVY MORNINGLORY 20 0 0 0 60 30 0 0 0 0 30 20 0 0 20 0 0 0 50 30 0 0 0 0 0 ERA WHEAT 20 20 10 0 30 0 0 30 0 0 20 0 0 0 0 0 0 0 0 0 0 0 20 0 0 SICKLEPOD 30 20 0 0 0 0 0 0 0 0 0 0 0 0 50 20 0 0 80 40 -- 0 30 0 0 JOHNSONGRASS 90 80 40 40 70 30 0 40 0 0 50 40 30 20 100 90 50 40 100 90 40 20 60 50 30 PURPLE NUTSEDGE 100 20 0 0 30 0 0 0 0 0 0 0 0 0 0 0 0 0 30 -- 0 0 0 0 0 G4646 CORN 0 0 0 0 0 0 0 0 0 0 30 20 0 0 10 0 0 0 10 0 0 0 0 0 0 WILD BUCKWHEAT 50 30 0 0 0 0 0 70 50 30 30 0 0 0 80 50 30 0 70 60 50 20 80 40 30 BLACKGRASS 60 40 40 30 50 40 30 50 30 0 70 30 20 0 90 50 20 0 70 50 30 10 40 30 10 ALTEX RAPE 80 80 70 30 70 50 30 0 0 0 30 20 0 0 90 70 50 30 70 60 60 40 70 60 50 KLAGES BARLEY 20 0 0 0 0 0 0 0 0 0 30 0 0 0 0 0 0 0 0 0 0 0 0 0 0 GREEN FOXTAIL 100 100 100 60 100 100 80 100 100 70 100 100 100 90 100 100 100 40 100 100 100 90 100 50 20 CHEAT GRASS 40 30 0 0 30 0 0    40 30 20 0 FIELD VIOLET 100 90 80 80 LAMBSQUARTER 30 0 0 0 70 50 30 50 30 0 90 80 50 40 100 100 90 80 100 90 90 80 100 90 80 CHICKWEED SPP.     70 50 30 0 0 0 30 0 0 0 40 10 0 0 70 40 0 0 30 0 0 DOWNY BROME        0 0 040 20 0 0 0 0 0 0 20 0 0 
    
     TEST C 
     Sixteen cm diameter Airlite plastic pots were partially filled with Tama silt loam soil and the soil saturated with water. Japonica and Indica rice seedlings a the 2.0 to 2.5 leaf stage were transplanted into 1/3 of the pots. Into another third of the pots were transplanted seedling or sprouted tubers of water plantain (Alisma trivale), Scripus (Scirpus paludosus), Cyperus (Cyperus esculentus), and arrowhead (Sagittaria spp.). The remaining pots were planted with barnyardgrass (Echinochloa crusgalli) seeds and sprouted tubes of water chestnut (Eleocharis spp.). These weeds all represent major rice weeds or genera of weeds important in rice. Three to four days after planting, the water level was raised to 3 cm (about 1200 ml/pot) and maintained a this level throughout the test. Chemical treatments were applied directly to the paddy water, within 24 hours of raising the water, after being formulated in a nonphytotoxic solvent. The pots were maintained in the greenhouse. Rates of application and plant response ratings made 21 days after treatment are summarized in Table C. 
     
                       TABLE C______________________________________         CMPD 669RATE = G/HA     1000   0500   0250  0125  0064______________________________________BARNYARDGRASS   100    90     98    98    90WATERCHESTNUT   0      0      0     0     0ARROWHEAD       0      0      0     0     0SCIRPUS         30     0      0     0     0YELLOW NUTSEDGE 80     60     0     0     0WATER PLAINTAIN 0      0      0     0     0RICE JAP EFF    0      0      0     0     0RICE INDICA EFF 0      0      0     0     0______________________________________         CMPD 35RATE = G/HA     1000   0500   0250  0125  0064______________________________________BARNYARDGRASS   95     100    80    100   70WATERCHESTNUT   0      0      60    40    60ARROWHEAD       95     50     40    0     0SCIRPUS         50     0      0     0     0YELLOW NUTSEDGE 100    95     60    0     0WATER PLAINTAIN 60     40     40    0     0RICE JAP EFF    20     0      0     0     0RICE INDICA EFF 20     0      0     0     0______________________________________          CMPD 35RATE = G/HA      2000   0500    0125  0032______________________________________RICE JAP TOL     50     50      20    0RICE INDICA TOL  60     55      55    0______________________________________         CMPD 18RATE = G/HA     1000    0500  0250  0125  0064______________________________________BARNYARDGRASS   60     40     0     0     0WATERCHESTNUT   50     40     0     0     0ARROWHEAD       35     20     0     0     0SCIRPUS         0      0      0     0     0WATER PLAINTAIN 40     20     0     0     0RICE JAP EFF    70     50     0     0     0RICE INDICA EFF 50     30     0     0     0______________________________________         CMPD 50RATE = G/HA     1000   0500   0250  0125  0064______________________________________BARNYARDGRASS   70     70     60    0     0WATERCHESTNUT   0      0      0     0     0ARROWHEAD       50     30     0     0     0SCIRPUS         0      0      0     0     0YELLOW NUTSEDGE 50     30     0     0     0WATER PLAINTAIN 0      0      0     0     0RICE JAP EFF    70     60     30    0     0RICE INDICA EFF 80     70     30    40    0______________________________________         CMPD 33RATE = G/HA     1000   0500   0250  0125  0064______________________________________BARNYARDGRASS   95     70     80    10    0WATERCHESTNUT   0      0      0     0     0ARROWHEAD       0      0      0     0     0SCIRPUS         0      0      0     0     0YELLOW NUTSEDGE 40     0      0     0     0WATER PLAINTAIN 0      0      0     0     0RICE JAP EFF    60     30     0     0     0RICE INDICA EFF 70     30     0     0     0______________________________________         CMPD 1381RATE = G/HA     1000   0500   0250  0125  0064______________________________________BARNYARDGRASS   100    100    60    55    55WATERCHESTNUT   0      0      0     0     0ARROWHEAD       0      0      0     0     0SCIRPUS         30     0      0     0     0YELLOW NUTSEDGE 50     40     0     0     0WATER PLAINTAIN 0      0      0     0     0RICE JAP EFF    60     40     20    0     0RICE INDICA EFF 60     40     20    0     0______________________________________         CMPD 1304RATE = G/HA     1000   0500   0250  0125  0064______________________________________BARNYARDGRASS   100    98     100   100   85WATERCHESTNUT   50     0      0     0     0ARROWHEAD       30     0      0     0     0SCIRPUS         80     70     65    0     0YELLOW NUTSEDGE 0      0      0     0     0WATER PLAINTAIN 65     0      0     0     0RICE JAP EFF    40     0      0     0     0RICE INDICA EFF 40     0      0     0     0______________________________________         CMPD 107RATE = G/HA     1000   0500   0250  0125  0064______________________________________BARNYARDGRASS   80     90     40    0     0WATERCHESTNUT   30     60     40    0     0ARROWHEAD       70     95     0     0     0SCIRPUS         80     80     60    0     0YELLOW NUTSEDGE 95     30     50    0     0WATER PLAINTAIN 80     60     0     0     0RICE JAP EFF    50     40     30    0     0RICE INDICA EFF 50     40     30    0     0______________________________________ 
    
     TEST D 
     The Corn and Sorghum Herbicide Test included the following species in both the preemergence and postemergence evaluations: 
     
         ______________________________________   SPECIESCategory  Common Name   Scientific Name______________________________________Crops     Corn          Zea mays     Soybean       Glycine max     Sorghum       Sorghum bicolorGrasses   Green foxtail Setaria viridis     Giant foxtail Setaria faberii     Johnsongrass  Sorghum halepense     Barnyardgrass Echinochloa crus-galli     Fall panicum  Panicum dichotomiflorum     Crabgrass     Digitaria sanguinalis     Nutsedge      Cyperus rotundusBroadleaves     Cocklebur     Xanthium pensylvanicum     Morningglory  Ipomoea hederacea     Velvetleaf    Abutilon theophrasti     Jimsonweed    Datura stramonium     Lambsquarters Chenopodium album     Pigweed       Amaranthus retroflexus     Smartweed     Polygonum persicaris______________________________________ 
    
     Postemergence 
     Postemergence plantings were grown in Sassafras sandy loam soil. Corn and soybeans were grown in separate 25 cm diameter containers. Sorghum and the seven grass weed species were grown in two 18 cm diameter containers, 4 species per container. The seven braodleaf weed species were also grown in two 18 cm diameter containers, 4 species in one container, 3 species in the second container. One additional planting of corn in an 18 cm diameter container was made. One additional planting of corn in an 18 cm diameter container was made. The soil surface of this additional container of corn was covered with the absorbent, perlite, before spray treatment so that test chemicals would enter the plant only via the foliage. The plants were grown 10-21 days, dependent upon the species and then sprayed postemergence with the test chemicals dissolved in a nonpytotoxic solvent. 
     Postemergence 
     Preemergence plantings were grown in fertilized Tama silt loam soil. These plantings are identical to those described in the postemergence section, with the exception of the corn planting having perlite covering the soil surface. These plantings were made the day of or the day before spraying the test chemicals dissolved in a nonphytotoxic solvent. 
     Evaluation 
     Treated plants and controls were maintained in the greenhouse for 2 to 4 weeks. Visual planting response ratings were made on a percentage scale of 0 to 100 in comparison with a control where 0=no injury, and 100=death. 
     The results are shown in Table D. 
     
                       TABLE D______________________________________             CMPD 50RATE GM/HA          0500    0250   0125 0064______________________________________PREEMERGENCEG4646 CORN          0       0      0    0WILLMS SOYBEANS     20      0      0    0GREEN FOXTAIL       85      50     30   0GIANT FOXTAIL       85      75     65   20FALL PANICUM        95      60     35   20LARGE CRABGRASS     100     100    75   40BARNYARDGRASS       45      20     0    0JOHNSONGRASS        95      90     70   35G522 SORGHUM        0       0      0    0PURPLE NUTSEDGE     30      0      0    0VELVETLEAF          65      40     25   0COCKLEBUR           25      0      0    0LADY SMARTWEED      40      20     0    0LAMBSQUARTER        90      75     35   0REDROOT PIGWEED     100     85     40   0IVY MORNINGLORY     65      40     30   0JIMSONWEED          70      50     25   0______________________________________                  CMPD 50RATE GM/HA             0500      0250______________________________________POSTEMERGENCEG4646 CORN             20       0WILLMS SOYBEANS        65       35GREEN FOXTAIL          0        0GIANT FOXTAIL          0        0FALL PANICUM           35       20LARGE CRABGRASS        100      70BARNYARDGRASS          0        0JOHNSONGRASS           40       20G522 SORGHUM           0        0PURPLE NUTSEDGE        0        0VELVETLEAF             25       0COCKLEBUR              40       25LADY SMARTWEED         40       30LAMBSQUARTER           80       65REDROOT PIGWEED        95       65IVY MORNINGLORY        60       20JIMSONWEED             45       20PERLITE CORN           0        0______________________________________           CMPD 33RATE GM/HA        1000     0500    0250______________________________________PREEMERGENCEG4646 CORN        0        0       0WILLMS SOYBEANS   0        0       0GREEN FOXTAIL     0        0       0GIANT FOXTAIL     0        0       0FALL PANICUM      0        0       0LARGE CRABGRASS   0        0       0BARNYARDGRASS     0        0       0JOHNSONGRASS      0        0       0G522 SORGHUM      0        0       0PURPLE NUTSEDGE   0        0       0VELVETLEAF        0        0       0COCKLEBUR         0        0       0LADY SMARTWEED    0        0       0LAMBSQUARTER      0        0       0REDROOT PIGWEED   0        0       0IVY MORNINGLORY   0        0       0JIMSONWEED        0        0       0______________________________________           CMPD 33RATE GM/HA        1000     0500    0250______________________________________POSTEMERGENCEG4646 CORN        0        0       0WILLMS SOYBEANS   0        0       0GREEN FOXTAIL     0        0       0GIANT FOXTAIL     0        0       0FALL PANICUM      0        0       0LARGE CRABGRASS   0        0       0BARNYARDGRASS     0        0       0JOHNSONGRASS      0        0       0G522 SORGHUM      0        0       0PURPLE NUTSEDGE   0        0       0VELVETLEAF        0        0       0COCKLEBUR         0        0       0LADY SMARTWEED    0        0       0LAMBSQUARTER      0        0       0REDROOT PIGWEED   0        0       0IVY MORNINGLORY   0        0       0JIMSONWEED        0        0       0PERLITE CORN      0        0       0______________________________________             CMPD 35RATE GM/HA          0500    0250   0125 0064______________________________________PREEMERGENCEG4646 CORN          0       0      0    0WILLMS SOYBEANS     0       0      0    0GREEN FOXTAIL       100     80     70   30GIANT FOXTAIL       100     80     50   0FALL PANICUM        100     80     50   0LARGE CRABGRASS     100     95     70   50BARNYARDGRASS       100     40     60   0JOHNSONGRASS        100     100    30   30G522 SORGHUM        0       0      0    0PURPLE NUTSEDGE     50      0      0    --VELVETLEAF          100     100    70   60COCKLEBUR           20      0      0    0LADY SMARTWEED      100     50     30   0LAMBSQUARTER        80      60     30   30REDROOT PIGWEED     98      50     0    0IVY MORNINGLORY     30      0      0    0JIMSONWEED          30      80     0    0______________________________________                  CMPD 35RATE GM/HA             0500     0250______________________________________POSTEMERGENCEG4646 CORN             0        0WILLMS SOYBEANS        30       10GREEN FOXTAIL          40       0GIANT FOXTAIL          60       0LARGE CRABGRASS        30       30BARNYARDGRASS          60       40JOHNSONGRASS           50       0G522 SORGHUM           50       0PURPLE NUTSEDGE        0        0VELVETLEAF             90       60COCKLEBUR              30       0LADY SMARTWEED         50       50LAMBSQUARTER           20       0REDROOT PIGWEED        70       30IVY MORNINGLORY        30       20JIMSONWEED             20       20PERLITE CORN           0        0______________________________________ 
    
     TEST E 
     Seeds of the following crops and weeds are sown into 15 cm pots containing Sassafras sandy loam soil: wheat (Triticum aestivum cv. Park), barley (Hordeum vulgare cv. Bonanza), sugarbeet (Beta vulgaris cv. USH-11), rapeseed (Brassica napus cv. Jet Neuf), black nightshade (Solanum nigrum), chickweed (Stellaria media), lambsquarter (Chenopodium album), Galium aparine, knotweed (Polygonum aviculare), Kochia scoparia, Matricaria indora, redroot pigweed (Amaranthus retroflexus), smartweed (Polygonum persicaria), speedwell (Veronica persica), wild buckwheat (Polygonum convolvulus), wild mustard (Brassica spp.), wild radish (Raphanus raphanistrum), annual bluegrass (PO annua), annual ryegrass (Lolium multiflorum), blackgrass (Alopercurus mysuroides), green foxtail (Setaria viridis), and wild oats (Avena fatua). Compounds are formulated in a nonphytotoxic solvent and applied to the plants as a foliar spray or applied to the soil surface. Plants are treated at two stages: preemergence, or postemergence when the sugarbeets are at the 2-3 true leaf stage. Plants are grown in a temperature-controlled greenhouse for the duration of the test. 
     Weed control and crop injury are evaluated visually at 3-4 weeks after compound application, using a scale of 0 to 100%, where 0=no injury and 100=complete death of the plant. All plants are rated with respect to untreated plants (checks) grown in the greenhouse under identical conditions to the treated plants. 
     The results are shown in Table E. 
     
                                           TABLE E__________________________________________________________________________        CMPD 51     CMPD 644     CMPD 52      CMPD 4RATE GM/HA   0500           0250              0125                  0064                    0500                        0250                           0125                              0064                                 0500                                    0250                                       0125                                          0064                                              0500                                                 0250                                                    0125                                                       0064__________________________________________________________________________POSTEMERGENCEPARK WHEAT   0  0  0   0 40  30 20 0  50 40 30 30  50 30 10 0BONANZA BARLEY        0  0  0   0 40  20 20 0  40 20 20 0   60 40 30 20BLACK NIGHTSHAD        60 40 0   0 20  10 0  0  70 10 0  0   90 70 30 10CMN CHICKWEED        0  0  0   0 0   0  0  0  0  0  0  0   0  0  0  0LAMBSQUARTER 40 20 0   0 40  20 0  0  10 0  0  0   70 20 20 0CTCHWD BEDSTRAW        50 0  0   0 30  30 30 0  100                                    70 80 20  100                                                 80 20 20KOCHIA       0  0  0   0 70  50 0  0  70 0  0  0   90 70 30 0SNTLS CHAMOMILE        60 40 20  0 90  50 50 20 85 50 50 20  85 70 50 30REDROOT PIGWEED        90 60 50  30                    60  50 50 50 90 90 50 0   90 90 40 20LADY SMARTWEED           100 100                           100                              0PERSN SPEEDWELL        40 20 0   0 80  40 20 0  90 60 30 40  100                                                 100                                                    70 20WILD BUCKWHEAT        0  0  0   0 0   0  0  0  30 0  0  0   70 40 0  0MUSTARD SPP. 30 30 30  0 50  50 20 20 50 20 0  0   80 40 40 20WILD RADISH  60 30 30  0 80  50 30 20 80 50 10 10  90 80 60 20ANN. BLUEGRASS        50 20 0   0 80  50 50 20 70 60 40 30  60 40 20 0ITALN. RYEGRASS        0  20 20  0 40  50 20 0  80 50 20 0   80 30 0  0BLACKGRASS   0  0  0   0 50  30 0  0  60 20 0  0   50 20 20 0GREEN FOXTAIL        0  0  0   0 50  50 30 30 75 40 0  0   80 20 20 0WILD OATS    0  0  0   0 20  20 0  0  30 20 0  0   30 0  0  0JET RAPE     20 0  0   0 30  0  0  0  40 20 0  0   30 20 20 0__________________________________________________________________________                             CMPD 51                                   CMPD 644                                         CMPD 52                                               CMPD                                                    CMPD 107                RATE GM/HA   0500  0500  0250  0500 0250__________________________________________________________________________                PREEMERGENCE                PARK WHEAT   0     30    70    80   30                BONANZA BARLEY                             30    50    70    80   30                BLACK NIGHTSHAD                             100   0     100   100  80                CMN CHICKWEED                             0     20    0     0    0                LAMBSQUARTER 100   85    100   100  90                CTCHWD BEDSTRAW                             0     0     100   100  0                KOCHIA       70    100   0     100  70                SNTLS CHAMOMILE                             100   100   100   100  70                REDROOT PIGWEED                             70    80    100   100  100                LADY SMARTWEED                 100                PERSN SPEEDWELL                             20    50    100   90   100                WILD BUCKWHEAT                             0     30    20    40   0                MUSTARD SPP. 0     0     50    50   20                WILD RADISH  0     0     50    50   60                ANN. BLUEGRASS                             20    80    100   100  20                ITALN. RYEGRASS                             0     0     70    70   0                BLACKGRASS   0     20    20    90   20                GREEN FOXTAIL                             100   100   100   100  100                WILD OATS    20    20    70    90   0                JET RAPE     0     20    20    40   30__________________________________________________________________________ 
    
     TEST F 
     Weed species were planted 3 or 4 per 15-cm diameter pot in Sassafras sandy loam (pH 6.8; 1% OM). Cotton was planted separately in the same sized pot. Postemergence plantings were made 12-16 days prior to treating so plants were in the 2- to 3-leaf stage (5-12 cm tall). Preemergence plantings were made the day before treating. Compounds were sprayed in a suitable non-phytotoxic solvent at 374 l/ha, then after 3 weeks of growth in a greenhouse, plant responsed were visually rated on a percent scale where 0=no injury and 100=plant death. The following species were included: 
     
         ______________________________________                           Planting                           DepthCommon Name  Latin Name         (cm)______________________________________Cotton (Coker 315)        Gossypium hirsutum 2Barnyardgrass        Echinochloa crus-galli                           1Bermudagrass Cynodon dactylon   1Broadleaf signalgrass        Brachiaria platyphylla                           1Crabgrass    Digitaria sanguinalis                           1Fall panicum Panicum dichotomiflorum                           1Goosegrass   Eleusine indica    1Johnsongrass Sorghum halepense  1Nutsedge     Cyperus rotundus   3Cocklebur    Xanthium pensylvanicum                           3Ivy leaf morningglory        Ipomoea hederacea  3Lambsquarters        Chenopodium album  1Pigweed      Amaranthus retroflexus                           1Prickly sida Sida spinosa       1Purslane     Portulaca oleracea 1Sicklepod    Cassia obtusifolia 3Smartweed    Polygonum persicaria                           1Velvetleaf   Abutilon theophrasti                           3Ground cherry        Physalis heterophylla                           1______________________________________ 
    
     The results are shown in Table F. 
     
                       TABLE F______________________________________        CMPD 4RATE GM/HA     0500    0250   0125  0064 0032______________________________________PREEMERGENCECOKER COTTON   0       0      0     0    0REDROOT PIGWEED          100     100    60    70   50LAMBSQUARTER   70      60     20    20   0VELVETLEAF     30      0      0     0    0PRICKLY SIDA   90      100    0     0    0SICKLEPOD      0       0      0     0    0COCKLEBUR      0       0      0     0    0CMN PURSLANE   80      30     30    20   0IVY MORNINGLORY          0       0      0     0    0GOOSEGRASS     100     100    100   80   80BERMUDAGRASS   100     100    95    20   0BARNYARDGRASS  95      0      0     0    0JOHNSONGRASS   50      50     20    0    0FALL PANICUM   100     100    90    90   90LARGE CRABGRASS          100     100    100   20   0BRDLF SGNLGRASS          30      0      0     0    0PURPLE NUTSEDGE          0       0      0     0    0LADY SMARTWEED 20      20     0     0    0GROUND CHERRY  0       0      0     0    0______________________________________