PATENT DOCUMENT

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.

Full Description:
CROSS-REFERENCE 
     This is a division of application Ser. No. 07/423,243, filed Oct. 18, 1989, now U.S. Pat. No. 4,980,367, which is a division of application Ser. No 07/134,261, filed Dec. 17, 1987, now U.S. Pat. No. 4,922,232 which is a continuation-in-part of application Ser No. 42,541, filed Apr. 29, 1987 (now abandoned, which in turn is a continuation-in-part of application Ser. No. 877,525, filed Jun. 23, 1986 (now 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 references 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 triasoles or imidazoles, amongst others of the formula: ##STR2## wherein 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 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; 
     X is --OCH 2  --, --CH 2  CH 2  -- or CH═CH; 
     Z is halogen, alkyl, cycloalkyl, alkoxy, alkythio, etc. 
     German Patent 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 ar antimycotics of treating dermatophytomycoses and systemic nycoses 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 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 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 perfluoralkyl 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  E 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 in 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##  perfluoroalkyl 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 substituted 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 or 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 of 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 of 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 compositions 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 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, 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 atoms, 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 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 1-2 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 or 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. 
     REFERRED 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 of 1-4 carbon atoms, haloalkyl of 1-4 carbon atoms, alkoxy of 1-4 carbon atoms, or S(O) m  R 5  ; and/or 
     2) n=O; 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-triasol-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)-S-buten-2-ol; and the (S) enantiomer thereof. 
     (h) 2-(4-Fluorophenyl)-3-(4-trifluoromethyl-phenyl)-1-(1H-1,2,4-triazol-1yl)-3-buten-2-ol; and the (S) enantimoer 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-trizol-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-trizol-1-yl)-3-buten-2-ol; and the (S) enantiomer thereof. 
     (n) 2-(2,4-Dichlorophenyl)-3-(2-chlorophenyl)-1-(1H-1,2,4-trizol-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-trizol-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-trizol-1-yl)-3-buten-2-ol; and the (S) enantiomer thereof. 
     (u) 2-(2-Fluorophenyl)-3-(4-chlorophenyl)-1-(1H-1,2,4-trizol-1-yl)-3-buten-2-ol; and the (S) enantiomer thereof. 
     (v) 2-(2,4-Difluorophenyl)-3-(4-chlorophenyl)-1-(1H-1,2,4-trizol-1-yl)-3-buten-2-ol; and the (S) enantiomer thereof. 
     (w) 2-(2-Chlorophenyl)-3-(4-fluorophenyl)-1-(1H-1,2,4-trizol-1-yl)-3-buten-2-ol; and the (S) enantiomer thereof. 
     (x) 2-(4-Chlorophenyl)-3-phenyl-1-(1H-1,2,4-triazol-1-yl)-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. 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 camphor-sulfonic 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 crystallisation. 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 etheral 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 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 haloketones starting material (IV), the product may be an oxirane (II), a halohydrins (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 expoxy-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 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 0044605, UK 2099818A, UK 146224, EP 1337718, and EP 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), -═H with strong base provides the 5-metalated triazoles (Ia) (See Heterocycles, 23, 1645-49, 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 THF 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-fluorobensoyl)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 suffcient 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)-3-buten-2-ol 
     A mixture of 10.2 g (0.040 mol) of crude 2-(4-fluorophenyl)-2-[1-(4-fluorophenyl)ethenyl]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/nexanes. 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.2Ph 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     P 4-Clh -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 H.sub.2 SO.sub.4 salt 180-182          175-180) 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 HNO.sub.3 salt 158-159    156-161) 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-Cl Ph 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.3Ph 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.3Ph -n-C.sub.4 F.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 4-ClPh 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     P 4-Brh -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.2Ph 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.2 Ph 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).sub.2Ph 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.2 Ph 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)Ph 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-FPh 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-FPh 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.2Ph 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-thio- 4-FPh 0 H CH.sub.3 H H H  phen-2-yl 339 2-Cl-thio- 4-FPh 0 H CH.sub.3 H H H  phen-3-yl 340 1-imida- 4-FPh 0 H CH.sub.3 H H H  soyl 341 1,2,4-tria- 4-FPh 0 H CH.sub.3 H H H  sol-1-yl 342 5-chloro-2- 4-FPh 0 H CH.sub.3 H H H  pyridyl 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 H.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    P 4-Fh 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- 4-FPh 0 H F H H H  thiophen-  2-yl 352 2-Cl- 4-FPh 0 H F H H H thiophen-  2-yl 353 1-imida- 4-FPh 0 H F H H H  soyl 354 1,2,4- 4-FPh 0 H F H H H  triazol-  1-yl 355 5-Cl-2- 4-FPh 0 H F H H H  pyridyl 356 4-FPh -n-C.sub.4 H.sub.9 0 H F H H H 357 4-FPh .sub.-t-C.sub.4 H.sub.9 0 H F H H H 358 4-FPh -n-C.sub.4 ##STR32## 
    
     EXAMPLES 1276 AND 1276 a: 
     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  =-82° (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##                   0 H H H H H 82-83                                    -62°1276a.sup.(1)  ##STR36##           ##STR37##                   0 H H H H H 83-84                                    +60°1277.sup.(2)  ##STR38##           ##STR39##                   0 H H H H H 60-61 (HCl salt 181-184)                                    -67°1277a.sup.(1),(2)  ##STR40##           ##STR41##                   0 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-triazool-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 ) δ 4.7 (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 compounds shown in Table 3 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.2Ph             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  2-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-FPh  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)δ4.9(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)δ3.8(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)δ0.92(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)δ2.7-3.5(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)δ2.7-3.4(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 acetonyl-acetonate. 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) δ 2.60 (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) δ 2.55 (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-CFPh  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-F Ph     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.3 Ph                 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-Cl Ph    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-FPh   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-(1B-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 ) δ 3.9 (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, 4H), 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__________________________________________________________________________ .sup.a NMR: (CDCl.sub.3) δ 4.5 (ABq, 2H), 4.8 (br s, 1H), 5.5 (two s, 2H), 6.7 (s, 1H), 6.9 (s, 1H), 7.0-7.6 (m, 10H) 
    
     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. Bezjak, J. Clinical Micro., 21, 509-512 (1984)] to a concentration of 10 7  organisms/ml and maintained at -70° until use. Test compounds are solublized 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 -70° 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  organisms/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 hours post-infection and then once daily for the next three 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##         MIC values (μg/ml)         C. albicans                 A. fumigatus______________________________________Example Number1                   ≦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       6.3Standards*Amphotericin 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 Assay      Days      7         14     21______________________________________Ex. No.  1          100         100    80  2          100         100    80  3          100         100    60  4          100         50     N.T.  6           50         10      0 10           20         10      0 15          100         90     60 16          100         100    100 17          100         90     70 25          100         100    50 26          100         100    100 26 salt     100         90     80 27          100         100    100 28          100         90     N.T. 32          100         90     50 33          100         100    100 34          100         100    100 34 salt     100         100    100 35          100         100    90 35 salt     100         100    70 39          100         80     N.T. 40          100         100    N.T. 41          100         100    N.T. 42           80         80     50 47           90         80     30 49          100         90     60 50          100         90     50 51          100         100    80 52          100         100    90 52 salt     100         100    90 55          100         70     50 65          100         70     50 67          100         100    100 85          100         80     70 94          100         40     10 99          100         100    40 100         100         50     30 101         100         90     60 114          70         10     10 117          60          0      0 163          90         60     40 164         100         80     70 208          0           0      0 286         100         50     20 359         100         80     80 360         100         60     40 361         100         100    90 363          10          0      0 453          60         40     30 594          70         10      0 596          70         60     40 603          10          0      0 608         100         70     20 620         100         100    90 622         100         100    100 627          0           0      0 644          80         70     50 646         100         100    70 651         100         50     20  656        100         90     40 657          0           0      0 661          50         20      0 667          10          0      0 668          70         10      0 669         100         100    100 671         100         100    60 675         100         60      0 685          30         10      0 721         100         30     30 724         100         90     40 725          90         90     40 726         100         80     10 905          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 continuos 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 sinc oxide or mixture 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 carriers for parental 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 carriers 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 is 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 colloidal 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 41.7% 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: 
     
         ______________________________________       Percent by Weight       Active       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 used. 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 by 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. and &#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. No. 3,235,361, Feb. 15, 1966, Col. 6, Line 16 through Col. 7, Line 19 and Examples 10 through 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, re-blended 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-                   98.5%(1H-1,2,4-triazol-1-yl)-3-buten-2-ol; andthe (S) enantiomer thereofsilica 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 Suspension______________________________________2-(2,4-difluorophenyl)-3-phenyl-1-                   25%1H-1,2,4-triazol-1-yl)-3-buten-2-ol; andthe (S) enantiomer thereofhydrated attapulgite    3%crude calcium ligninsulfonate                   10%sodium dihydrogen phosphate                   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)-                    30%1-(1H-1,2,4-traizol-1-yl)-3-buten-2-ol; andthe (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)-                    15%1-(1H-1,2,4-triazol-1-yl)-3-buten-2-ol; andthe (S) enantiomer thereofblend of calcium sulfonates                    25%and nonionic surfactantsxylene                   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 (chloroethalonil) 
     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-methyl)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-tolyl]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 93-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)carbonylox]]-bis[ethanimidothioate] (thiodicarb) 
     phosphoroethiolothionic 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)-α-(methylethyl)benzenacetate (flucythrinate) 
     O,O-diethyl-O-(3,5,6-trichloro-2-pyridyl)phosphorothioate (chlorpyrifos) 
     O,O-dimethyl-S-[(4-oxo-1,2,3-bensotriazin-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, non-limiting 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-         dimethylureachlorpropham  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-phenylpyrridiniumcyprazine     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       1,2-dimethyl-3-phenylureafenuron TCA   1,2-dimethyl-3-phenylurea         mono(trichloracetate)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.--         m-         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.sup. ™         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 acid, 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 inaequalis, 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 220° 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 casual 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 pont 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 mod, 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 what 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 orysae, 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 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 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 then 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, an 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=axillary simultation; 
     S=albinism; and 
     Y=abscised buds or flowers. 
     
         TABLE A  POSTEMERGENCE CMPD 52 CMPD 52 (salt) CMPD 56 CMPD 56 (salt) CMPD 57 CMPD 58 CMPD 59 CMPD 61 CMPD 66 CMPD 67 CMPD 99   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 COKER COTTON 2H 2H 0 7F,9G 4H 10P,9G 10P,9G 0 2H 10P,9G 10P,9G 5H CULT MORNINGLRY 2C,4H 3C,6H 0 4C,9G 3C,7G 5C,9G 2C,3G 3C,5H  5C,9G 2C,2G 2C,4H COCKLEBUR 0 2C 0 3H,8G 2C 1H 2C,8H 0 1C 2C,5H 2C,5G 4C,7H PURPLE NUTSEDGE 0 --  0 0 5G 0 0 0 0 0 0 LARGE CRABGRASS 0 3C,6G 0 4G 0 9C 2C,8H 0 0 0 4G 9G BARNYARDGRASS 0 0 0 5G 0 7H 0 0 0 0 0 0 WILD OATS 0 2C,4G 0 0 0 0 0 0 0 0 0 0 ERA WHEAT 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 WILLMS SOYBEANS 0 1C 0 3C,8G 1C 4C,9G 4C,9G 1C,1H 3H 3C,4H 1C,4H 3C,5H RICE DRY SEEDED 0 1C 0 0 0 0 0 0 0 0 0 0 G522 SORGHUM 0 0 0 0 0 0 0 0 0 0 0 0 CHEAT GRASS   0 0  0 0   0 0 0 USN11 SUGARBEET 0 4G 0 5H,5I 2H 4H,5I 3H,7G 4H 3H 8H,5I 7H,5I 7H VELVETLEAF 3G 2C,5G 0 7G 2G 4C,9G 2C,8G 0 3C,5G 3G 2C,5G 8G GIANT FOXTAIL 0 2C,5G 0 0 0 9G 0 0 0 0 0 0 KLAGES BARLEY 0 0 0 0 0 0 0 0 0 0 0 0 DOWNY BROME 0 0 0   0 0    CMPD 101 CMPD 106 CMPD 107 CMPD 108 CMPD 208 CMPD 594 CMPD 594 CMPD 596 CMPD 598 CMPD 603 CMPD 605 CMPD 611   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 COKER COTTON 9G,10P 4G 10P,8G 6H 0 4G 3G 0 8G 0 0 7G CULT MORNINGLRY 5C,9H 2C,8G 5C,9G 3C,6G 2C,5H 6G 2C,2H 2C 0 3B 2B 0 COCKLEBUR 3C,6H 2C,2H 3C,5G 2C,2H 2C 2C 0 1C 2C 1B 1B 1H PURPLE NUTSEDGE 0 5G 0 0 5G  0 0 3G 0 0 0 LARGE CRABGRASS 7G 2G 0 0 0 2G 2G 0 2G 0 0 5G BARNYARDGRASS 0 5H 7H 0 0 0 0 0 0 0 0 2C WILD OATS 0 0 0 0 0 0 0 0 2G 0 0 0 ERA WHEAT 0 0 0 0 0 0 0 0 3G 0 0 0 G4646 CORN 0 0 0 0 0 0 2G 0 0 0 0 0 WILLMS SOYBEANS 2C,4H 2C,5G 5C,9G 2C,7G 2C,2H 2B,3H 2C,3H 2C 2C,2H 0 1C 2C,4H RICE DRY SEEDED 0 0 2C,5G 0 0 3G 0 0 0 0 0 0 G522 SORGHUM 0 0 0 0 0 0 0 0 0 0 0 0 CHEAT GRASS 0 0   0 0 0 0 0 0 0 0 USN11 SUGARBEET 6H 5G 0 3C,6G 6H 0 3G 1H 4G,5I 0 0 0 VELVETLEAF 9H 3C,7G 3C,6G 2C,5G 8G 2C 0 1C 0 1B 0 0 GIANT FOXTAIL 0 0 0 0 0 0 2G 0 3G 0 0 0 KLAGES BARLEY 0 0 0 0 0 0 0 0 0 0 0 0 DOWNY BROME   0 0   CMPD 618 CMPD 620 CMPD 624 CMPD 627 CMPD 644 CMPD 644 CMPD 646 CMPD 648 CMPD 651 CMPD 653 CMPD 656 CMPD 658   RATE = KG/HA 2 0.4 2 0.4 0.4 2 0.1 0.4 0.4 0.4 0.4 0.4 0.4 0.4 COKER COTTON 6P,9G 3H 10P,9G 2H,9G 1C  5G 2C,7G 9G,10P 9P,9G 0 10P,9G 7G 0 CULT MORNINGLRY 0 2C,5G 3C,8G 2C,3H 2C,6G 6C,9G 3C,3G 3C,5G 3C,8G 1C 2C 2C 2C,3H 0 COCKLEBUR 1H 2C,2H 3C,9G 2C,5H 2C 5C,8H 0 2C 2C 2C 1C 2C,5G 2C 0 PURPLE NUTSEDGE 0 0 5G 0 0 8G,5X 0 0 0 0 0  2G 0 LARGE CRABGRASS 8G 9G 2C,9G 9C 0 3C,9G 0 0 6G 0 0 5C,9G 2G 0 BARNYARDGRASS 0 2H 3C,9H 6H 0 5C,9H 0 0 0 0 0 0 0 0 WILD OATS 0 0 0 0 0 3C,6G 0 0 0 0 0 0 0 0 ERA WHEAT 0 0 0 2G 0 4C,8G 0 0 0 0 0 0 0 0 G4646 CORN 0 3C,3H 3C,7H 0 0 3C,6H 0 0 0 0 2G 2G 0 0 WILLMS SOYBEANS 2C,4G 3C,8G 4C,9G 3C,8H 1H 9C 2C,2H 2C,5H 5C,8H 2C 1C 3C,7G 2C 0 RICE DRY SEEDED 0 2C,4G 2C,8G 0 0 3C,8G 0 1C 0 0 0 0 0 0 G522 SORGHUM 0 2C 2C,3H 0 0 3C,9H 0 0 0 0 0 0 0 0 CHEAT GRASS 0 0 8G 0 0 2C,8G   0 0 0 0 0 0 USN11 SUGARBEET 5H 3H 8H 7H,5I 2H 5G,5I 2G 7G 4H 4G,5I 1H 2C,7H 4H 0 VELVETLEAF 2C,7G 3C,5H 2C,9G 1C 0 9G 3G 2C,6G 2C,3G 2C,5G 0 1C  8G GIANT FOXTAIL 8G 2C,7H 9G 2C,9G 0 3C,9G 0 2C,3G 0 0 0 2C,7H 0 0 KLAGES BARLEY 0 0 0 0 0 2C,9G 0 0 0 0 0 0 0 0 DOWNY BROME       0 0    CMPD 659 CMPD 661 CMPD 669 CMPD 673 CMPD 675 CMPD 721 CMPD 724 CMPD 724 CMPD 726 CMPD 753 CMPD 754 CMPD 782   RATE = KG/HA 0.4 0.4 2 0.4 0.4 0.4 0.4 0.4 0.4 0.4 0.4 0.4 COKER COTTON 0 1C,3H 3C,7H 10P,9G 0 5G 6G 10P,9G 4H 10P,9G 2H 10P,9G CULT MORNINGLRY 3C,6G 1C 6C,9G 2C,1H 1C 3C,6H 3C,5H 5C,9G 3C,7G 4C,9G 5C,9G 5C,9G COCKLEBUR 2C 1C 3C,7G 2C,3H 0 2C 3C,4H 3C,9H 1C,2H 2C,6G 2C,3H 8G PURPLE NUTSEDGE 0 0 4G 0 0 0 2C,8H 0 0 0 0 0 LARGE CRABGRASS 0 0 2G 3C,3G 0 0 9G 5G 0 4C,9G 0 5C,9G BARNYARDGRASS 0 0 5C,9G 0 0 0 2C,3H 7G 0 5H 0 7H WILD OATS 0 0 2C,4G 0 0 0 0 0 0 0 0 0 ERA WHEAT 0 0 2G 0 0 0 0 2G 0 0 0 0 G4646 CORN 0 0 0 0 0 0 0 0 2G 0 0 0 WILLMS SOYBEANS 3C 1H 5C,9G 1C,1H 1C 2C 4C,8H 3C,9G 2H 9C 2C,3H 8G RICE DRY SEEDED 0 0 0 0 0 0 5G 0 0 0 0 0 G522 SORGHUM 0 0 2G 0 0 0 0 0 0 2G 0 0 CHEAT GRASS 0 0 3G 0 0 0 0 0 0 0  0 USN11 SUGARBEET 0 4H 5G,5I 8H,5I 1C 3H 7H 3H 3H 8H 7G 7H,5I VELVETLEAF 2C,5G 1C 6G 1C 0 6G 9H 3C,9G 0 3C,8G 3G 8G GIANT FOXTAIL 0 0 2G 9H 0 0 9G 9G 5G 2C,8G 0 7G KLAGES BARLEY 0 0 2G 0 0 0 0 0 0 0 0 0 DOWNY BROME           0   CMPD 784 CMPD 810 CMPD 811 CMPD 815 CMPD 863 CMPD 879 CMPD 905 CMPD 1276 CMPD 1276 (salt) CMPD 1276A  CMPD 1277   RATE = KG/HA 0.4 0.4 0.4 0.4 2 0.4 0.4 0.4 0.4 0.4 0.4 0.4 COKER COTTON 10P,9G 0 10P,9G 9G,10P 2B 2C,6G 0 0 4H 9G,10P 7G 3H,6G CULT MORNINGLRY 3H 2C,5G 5C,9G 3C,9H 0 1C,2G 1C,2H 2C 2C,4H 2C,3G 1C 2C,3G COCKLEBUR 2H 8G 3H,8G 2C,4H 0 2C 1C 0 2C 3C 1C 2C,7G PURPLE NUTSEDGE 0 0 0 0 0 0 0 0 0  0 LARGE CRABGRASS 6H 5G 9C 0 1B 0 3G 0 0 0 0 4G BARNYARDGRASS 0 2G 3C,9G 0 1B 0 0 0 0 0 0 1C WILD OATS 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 G4646 CORN 0 0 0 0 1B 0 0 0 0 0 0 0 WILLMS SOYBEANS 2C,5H 5G 3C,9G 0 2B 2C 2H,5G 0 2C,6H 3C 2H,6G 1C,1H RICE DRY SEEDED 0 0 0 0 0 0 2G 0 0 0 0 0 G522 SORGHUM 0 0 0 0 0 0 0 0 0 0 2G 0 CHEAT GRASS 0 0 0 0 0 0 0 0 0 0 0 0 USN11 SUGARBEET 7H 4G 6H,5I 0 1B 0 3G 0 2H 0 3H 1H VELVETLEAF 2H 8G 4C,9G 0 2B 2C 2G 0 8G 2C,4G 2C 0 GIANT FOXTAIL 2G 2G 9G 0 1B 0 0 0 0 0 0 3G KLAGES BARLEY 0 0 0 0 0 0 0 0 0 0 0 0 DOWNY BROME   CMPD 1278 CMPD 1279 CMPD 1280 CMPD 1377 CMPD 1381 CMPD 1304 CMPD 1  CMPD 4 CMPD 9 CMPD 11 CMPD 13   RATE = KG/HA 0.4 0.4 0.4 0.4 2 0.4 2 0.4 2 0.4 0.4 0.1 0.4 2 0.4 COKER COTTON 0 10P,9G 7G 9G,10P 9G,10P 3G 10P,9G 5H 10P,9G 3H 3C,9H 3H 3H 10P,9G 6H CULT MORNINGLRY 1C 5C,9G 2H 2C,6H 4C,9H 3C,5G 2C,8H 3C,7G 2C,7G 1C,1H 4C,8H 3C,4H 3C,6G 4C,9G 4C,8G COCKLEBUR 1C 5H 4H 2C,3H 4C,9H 2C 2C,7H 2C,4G 8H 1C,3G 3C,8H 0 3C,6G 3C,9G 3C,3H PURPLE NUTSEDGE 0 0 0 -- 4G 0 2C,5G 0 8G 0 5G 0 9G 7G 0 LARGE CRABGRASS 4G 3C,5G 9H 0 4C,9G 2G 4C,9G 3C,7G 3C,9G 0 9G 0 3G 9C 0 BARNYARDGRASS 0 2G 5H 2G 5C,9H 2H 9H 5H 9H 0 2C,8H 0 0 5C,9G 0 WILD OATS 0 0 0 0 0 0 2G 0 2G 0 0 0 0 7G 0 ERA WHEAT 0 0 0 0 0 0 2G 0 4G 0 0 0 0 8G 0 G4646 CORN 0 0 0 0 0 0 3G 0 3G 2G 2G 0 0 7H 0 WILLMS SOYBEANS 0 3C,5G 5C,9G 3C,5H 3C,6H 2C,4G 2C,8G 2C,5G 2C,6G 2C,3H 4C,8G 1C,1H 2C,4H 4C,9G 3C,5G RICE DRY SEEDED 0 0 0 0 0 0 8G 0 7G 0 5G 0 1C 3C,7G 0 G522 SORGHUM 0 0 2G 0 0 0 9H 0 7G 0 5G 0 0 3C,8H 2G CHEAT GRASS 0 0 0 0 2G -- 2G -- 5G 0 5G   7G USN11 SUGARBEET 1H 7H,5I 8H 6H,5I 7H,5I 5G 9H 2H 7H,5I 8G 6H 3G 3G 9H,5I 7G VELVETLEAF 0 3C,7G 7H 2C,3H 3C,7H 0 9G 0 9G 0 2C,8H -- 4G 3C,9G 2C GIANT FOXTAIL 0 0 9H 0 3C,9H 0 9G 0 9H 0 9G 0 2C,2G 9G 3G KLAGES BARLEY 0 0 0 0 0 0 2G 0 3G 0 0 0 0 5G 0 DOWNY BROME      0 -- 0 --   0 0  0   CMPD 15 CMPD 16 CMPD 17 CMPD 18 CMPD 23 CMPD 33 CMPD 34 CMPD 34 CMPD 34 CMPD 35 CMPD 35 (salt)   RATE = KG/HA 0.4  0.4 0.4 0.4 0.4 0.4 0.4 0.4 0.4 0.4 2 2 COKER COTTON 7G 8G 3H 7G,5I 2H 10P,9G 10P,8G 8P,8G 4G 10P,9G 10P,9G 10P,9G CULT MORNINGLRY 2C,4H 4C,9G 3C,4G 2C 2C,3H 2C,5G 3C,10P 5C,9G 0 10P,9G 4C,9G 5C,9G COCKLEBUR 2C 2C,6G 2C,5G 2C,3G 1C,1H 3C,4H 2C,2H 2C,2H 2C,3H 2C,5G 3C,8G 4C,9H PURPLE NUTSEDGE 0 0 0 0 0 0 0 0 0 2G 8G 8G LARGE CRABGRASS 0 8G  3C,7G 3G 5C,9G 3G 0 5G 2C,9G 3C,9G 3C,9G BARNYARDGRASS 3G 0 0 9H 0 0 0 0 5H 2C,8H 4C,9H 5C,9G WILD OATS 0 0 0 0 0 0 0 0 0 0 1C 0 ERA WHEAT 0 0 0 0 0 0 0 0 0 0 0 0 G4646 CORN 0 0 0 0 0 2G 0 0 0 1C,3H 3C,7H 3C,7H WILLMS SOYBEANS 3C,5H 2C,2H 1C,2H 3C,5G 1C,1H 4C,9G 4C,9G 2C,3H 4C,7G 10P,9G 3C,9G 4C,9G RICE DRY SEEDED 0 2C 1C 0 0 0 2G 0 0 1C 3C,9G 4G G522 SORGHUM 0 0 0 0 0 0 0 0 0 0 3C,9H 7G CHEAT GRASS 0 0 0 0 0 0    0 5G 4G USN11 SUGARBEET 5H 2G 7H 3G,5I 4H 8H,5I 7H 3G 6G 5H 2C,8H 3H,7G VELVETLEA F 6G 6G 0 2C,5G 0 3C,8G 5C,8G 3C,8G 5C,9G 4C,8G 4C,9G 7C,9G GIANT FOXTAIL 0 7G 3G 5G 2G 9G 0 0 0 8H 9G 3C,9G KLAGES BARLEY 0 0 0 0 0 0 0 0 0 0 1C 6G DOWNY BROME       3G 0 0    CMPD 35 (salt) CMPD 35 (salt) CMPD 35 (salt) CMPD 39 CMPD 42 CMPD 47 CMPD 51 CMPD 52   RATE = KG/HA 0.4 0.4 0.4 0.4 0.4 0.4 2 2 COKER COTTON 3H 0 9P,8G 8G,10P 1C 10P,8G 1C,6H 3H,8G CULT MORNINGLRY 3C,8G 0 2C,2H 2C 2C 1C 5G 5C,9G COCKLEBUR 2C,1H 0 2C,2H 2C 3C 1C 2C,7H 3C,9H PURPLE NUTSEDGE 0 0 0 0 0 0 0 LARGE CRABGRASS 0 0 0 0 0 0 2C,9G 3C,9G BARNYARDGRASS 0 0 5H 0 0 0 2C,7G 5C,9G WILD OATS 0 0 0 0 0 0 2C,2G 2C,4G ERA WHEAT 0 0 0 0 0 0 2C,3G 2C,6G G4646 CORN 2H 0 2G 0 0 2G 2C,6H 2C,6G WILLMS SOYBEANS 3C,9G 2G 9G,5I 2C 1H 2C,2H 3C,7H 4C,9G RICE DRY SEEDED 0 0 0 0 0 0 2C,5G 2C,6G G522 SORGHUM 0 0 0 0 0 0 0 9H CHEAT GRASS   0 0 0 0 5G 2C,6G USN11 SUGARBEET 7G 2G 4H 4H 3H 0 7G 3H,7G VELVETLEAF 3C,5G 0 3C,8H 4H 5C 0 4G 7C,9G GIANT FOXTAIL 2G 0 0 0 2G 0 2C,7G 1C,9G KLAGES BARLEY 0 0 0 0 0 0 0 6G DOWNY BROME 0 0   PREEMERGENCE CMPD 52 CMPD 52 CMPD 56 CMPD 56 CMPD 57 CMPD 58 CMPD 59 CMPD 61 CMPD 66 CMPD 67 CMPD 99 CMPD 101   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 COKER COTTON -- 2G 0 5G 0 7G 8G 0 0 0 0 0 0 CULT MORNINGLRY 0 8H 0 4C,9G 0 4C,9G 8G 0 0 0 0 8H 2C,9H COCKLEBUR 2G 2C,2G 0 2G 0 0 3G 0 0 0 0 0 0 PURPLE NUTSEDGE 0 0 0 5G 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 BARNYARDGRASS 0 9C 5G 7C,9H 0 9C 4C,9H 0 0 0 3G 2G 2G WILD OATS 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 G4646 CORN 0 0 0 0 0 2G 3G 0 0 0 0 0 0 WILLMS SOYBEANS 0 0 0 7G 0 3C,9G 4G 0 0 0 1H 0 0 RICE DRY SEEDED 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 CHEAT GRASS   0 5G  9G 3G   0 3G 0 0 USN11 SUGARBEET 0 5H 0 6G 2H 7H 9G 0 0 5G 7G 3H 0 VELVETLEAF 0 4C,8H 0 4C,9G 0 5C,9G 5G 0 0 2G 0 0 0 GIANT FOXTAIL 3C,9H 9H 0 9H 4C,9G 9H 3C,9G 0 7G 3G 5G 2C,9H 7G KLAGES BARLEY 0 0 0 0 0 2G 0 0 0 0 0 0 0 DOWNY BROME 2G 3C,8G   0   0 0    CMPD 106 CMPD 107 CMPD 108 CMPD 208 CMPD 594 CMPD 594 CMPD 596 CMPD 598 CMPD 603 CMPD 605 CMPD 611 CMPD 618   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 2 COKER COTTON 0 3G 0 0 0 3G 3G 0 0 0 0 4G CULT MORNINGLRY 0 5C,9G 3H 0 0 0 0 0 0 0 0 2H COCKLEBUR 0 0 0 0 0 0 2G 2G 0  0 0 PURPLE NUTSEDGE 0 0 10E 0 0 0 10E 0 0 0 0 &amp;E LARGE CRABGRASS 4C,9H 5C,9G 9G 0 9G 2U,9G 9H 3C,9G 0 3G 8G 8H BARNYARDGRASS 0 9H 0 0 4C,8H 2C,8G 3C,7H 2G 0 0 2C,6G 5C,9H WILD OATS 0 0 0 0 0 3G 0 0 0 0 0 0 ERA WHEAT 0 0 0 0 0 0 0 0 0 0 0 3G G4646 CORN 0 0 0 0 0 2G 2G 0 0 0 0 3G WILLMS SOYBEANS 2G 0 0 0 0 0 0 0 0 0 0 0 RICE DRY SEEDED 0 0 0 0 0 4G 0  0 0 0 2G G522 SORGHUM 0 2H 0 0 0 3G 2C,9H  0 0 0 0 CHEAT GRASS 0   0 2G 3G 0  0 0 0 2G USN11 SUGARBEET 3H 3H 0 2H 2G 4G 3G  0 0 0 7G VELVETLEAF 0 5G 0 0 4G 5G 2G  0 0 0 5G GIANT FOXTAIL 3C,9G 3C,9G 8H 0 9G 3C,9G 9H  0 0 3C,8G 9H KLAGES BARLEY 3G 0 0 0 0 0 0 0 0 0 0 0 DOWNY BROME  0 0   CMPD 620 CMPD 624 CMPD 627 CMPD 644 CMPD 644 CMPD 646 CMPD 648 CMPD 651 CMPD 653 CMPD 656 CMPD 658 CMPD 659   RATE = KG/HA 0.4 2 0.4 0.4  0.1 0.4 0.4 0.4 0.4 0.4 0.4 0.4 0.4 COKER COTTON 9G 9G 0 0 8G 0 0 0 0 0 5G 0 0 3G CULT MORNINGLRY 2C,8G 9G 2G 0 9G 0 2C 0 0 0 2C,5G 0 0 1C COCKLEBUR 3C,7G 2H 2G  3C,7G 0 0 0 0 0 2H 0 2G 0 PURPLE NUTSEDGE 5G 0 0 0 10E 10E 10E 0 0 0 0 2G 6G 10E LARGE CRABGRASS 9H 9H 9H 0 9H 3C,7H 5C,9H 9G 3C,8G 0 9C 5C,9H 9H 3C,9G BARNYARDGRASS 2C,5H 7C,9H 8H 0 9C 0 5C,9H 0 0 0 3C,9G 0 5G 2C,5G WILD OATS 0 0 0 0 4C,8G 0 2C,5G 0 0 0 0 0 0 0 ERA WHEAT 0 0 0 0 9G 0 0 0 0 0 2G 0 0 0 G4646 CORN 0 1H 0 0 2C,8H 0 0 0 2G 0 0 0 4G 0 WILLMS SOYBEANS 7G 8G 0 0 8G 0 0 3H 0 0 0 0 2G 0 RICE DRY SEEDED 3G 2G 2G 0 6G 0 0 0 0 0 0 0 0 0 G522 SORGHUM 9G 9G 0 0 3C,9G 0 4G 0 0 0 7G 0 0 0 CHEAT GRASS 0 2G 0 0 7G   0 2G 0 8G 0 0 0 USN11 SUGARBEET 8H 9H 8H 0 9G 0 6H 5H 7H 0 8H 2H 0 0 VELVETLEAF 6G 9H 8G 0 6C,9G 0 2C 2G 4G 0 5C,9G 0 0 7G GIANT FOXTAIL 9H 9H 9H 0 9H 3C,9H 5C,9H 9H 2C,9G 0 5C,9H 4C,9H 7H 3C,9H KLAGES BARLEY 0 0 0 0 3G 0 0 0 3G 0 0 0 0 0 DOWNY BROME      0 3C,5G    CMPD 661 CMPD 669 CMPD 673 CMPD 675 CMPD 721 CMPD 724 CMPD 724 CMPD 726 CMPD 753 CMPD 754 CMPD 782 CMPD 784   RATE = KG/HA 0.4 2 0.4 0.4 0.4 0.4 0.4 0.4 0.4 0.4 0.4 0.4 COKER COTTON 0 8G 0 0 0 0 8G 0 3G 0 0 0 CULT MORNINGLRY 0 5C,9H 0 0 3H 2C,8H 9C 0 9G 0 3C,9H 1H COCKLEBUR 0  0  0 0 0 2G 3H 0 0 0 PURPLE NUTSEDGE 0 3G 0 0 0 0 0 0 9G 0 0 5G LARGE CRABGRASS 5G 9H 9H 0 7G 2C,9H 4C,9H 7G 9G 8G 3C,9G 9H BARNYARDGRASS 0 9C 4H 0 0 5C,9H 5C,9H 3C,6G 8G 2H 2C,9H 0 WILD OATS 0 2C 0 0 0 0 0 0 0 0 0 0 ERA WHEAT 0 0 2G 0 0 0 0 0 0 0 0 0 G4646 CORN 0 2C,5H 2G 0 0 0 0 2G 0 0 0 0 WILLMS SOYBEANS 0 8G 0 0 0 0 6G 0 3G 0 3G 0 RICE DRY SEEDED 0 0 0 0 0 0 0 0 0 0 0 0 G522 SORGHUM 0 9G 0 0 0 0 6G 0 5G 0 6G 2G CHEAT GRASS 0 0 3G 0 0 0 8G 0 0  0 0 USN11 SUGARBEET 5G 8G 6H 0 2C,3H 5H 8G 2H 8H 3G 9G 5G VELVETLEAF 0 4C,8G 0 0 2G 9G 4C,9G 0 4G 0 2C,8G 4G GIANT FOXTAIL 3G 9H 2C,8G 0 7G 3C,9H 9H 2C,9H 3C,9G 7G 9H 3G KLAGES BARLEY 0 0 2G 0 0 0 0 0 0 0 0 0 DOWNY BROME    0   CMPD 810 CMPD 811 CMPD 815 CMPD 863 CMPD 879 CMPD 905 CMPD 1276 CMPD 1276 CMPD 1276A CMPD 1277    RATE = KG/HA 0.4 0.4 0.4 2 0.4 0.4 0.4 0.4 0.4 0.4 0.4 COKER COTTON 0 9G 0 0 5G 0 0 0 0 0 0 CULT MORNINGLRY 0 9C 0 0 0 0 0 0 1C,3G 0 0 COCKLEBUR 2G 0   2G 0  0 0 0 0 PURPLE NUTSEDGE 0 10E 0 0 4G 8G 0 0 8G 10E 0 LARGE CRABGRASS 9H 5C,9H 9G 0 4G 9H 0 4C,9H 7G 0 5C,9G BARNYARDGRAS S 4C,9H 7C,9H 0 0 3G 4C,8H 0 4C,8H 0 0 3C,8H WILD OATS 2G 0 0 0 2G 0 0 0 0 0 0 ERA WHEAT 2G 0 0 0 0 0 0 0 0 0 0 G4646 CORN 0 2G 0 0 0 2G 0 0 0 0 2G WILLMS SOYBEANS 0 7G 0 0 0 2G 0 0 0 0 0 RICE DRY SEEDED 0 0 0 0 0 0 0 0 2G 0 0 G522 SORGHUM 0 8G 0 0 0 0 0 0 0 0 0 CHEAT GRASS 3G 5G 0 0 2G 2G 0 0 0 0 0 USN11 SUGARBEET 9G 8G 0 0 0 5H 0 2H 7G 6G 7H VELVETLEAF 3G 2C,9G 3G 0 0 4G 0 0 4G 8G 3G GIANT FOXTAIL 9H 9H 2G 0 8G 9H 0 4C,9H 2C,9G 0 3C,9H KLAGES BARLEY 0 2G 0 0 0 0 0 0 0 0 0 DOWNY BROME   CMPD 1278 CMPD 1279 CMPD 1280 CMPD 1377 CMPD 1381 CMPD 1304 CMPD 1 CMPD 4 CMPD 9 CMPD 11   RATE = KG/HA 0.4 0.4 0.4 0.4 2 0.4 2 0.4 2 0.4 0.4 0.1 0.4 2 COKER COTTON 0 0 2G 0 7G 0 8G 0 7G 0 8G 0 5H 9G CULT MORNINGLRY 0 0 2H 2C 2C,3G 0 7H 0 7G 0 9H 0 1C 9G COCKLEBUR 0 0 0 0 2G 0 3G 0 0 0 0 0 0 2C,8G PURPLE NUTSEDGE 0 0 0 0 9G 0 0 0 3G 5G 0 0 8G 10E LARGE CRABGRASS 0 7G 9H 4C,8H 5C,9H 5C,9G 3C,9G 4C,9H 4C,9G 4C,9G 9C 3C,7H 4C,9H 9H BARNYARDGR ASS 0 2G 3G 2G 10C 3H 5C,9H 0 5C,9H 1C 10C 4C,6H 9C 5C,9H WILD OATS 0 0 0 0 0 0 0 0 2G 0 0 0 0 8G ERA WHEAT 0 0 0 0 0 0 0 0 0 2G 0 0 2G 2C,9G G4646 CORN 0 0 0 0 0 0 3G 0 5G 0 0 0 2C,2H 3C,8H WILLMS SOYBEANS 0 0 0 0 5G 0 9G 0 7G 2G 0 0 3C,7H 9G RICE DRY SEEDED 0 0 0 0 0 0 4G 0 0 3G 0 0 0 0 G522 SORGHUM 0 0 0 0 2C,6G 0 7G 3G 9G 0 9H 0 2C,9G 9H CHEAT GRASS 0 0 0 0 0 -- 0 -- 6G 0 0   3C,8G USN11 SUGARBEET 0 3H 5G 2C,6H 8G,5I 2H 8H 0 8H 4H 8H 3H 6H 9H VELVETLEAF 0 5G 5G 3G 7G 3G 8G 5G 7G 5G 7H 0 5C,9H 9G GIANT FOXTAIL 2G 8G 9H 3C,9H 4C,9H 4C,9H 9H 3C,9H 9H 3C,9H 3C,9H 4C,9H 4C,9H 9H KLAGES BARLEY 0 0 0 0 0 0 0 0 0 0 0 0 0 4G DOWNY BROME      0 -- 0 --   0 2C,7G   CMPD 13 CMPD 15 CMPD 16 CMPD 17 CMPD 18 CMPD 23 CMPD 33 CMPD 34 CMPD 34 CMPD 34 CMPD 35   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 2 COKER COTTON 0 0 5G 0 0 0 8G 0 0 0 6G 8H CULT MORNINGLRY 0 0 0 0 1H 0 7G 6G 8G 2C,8G 8H 9H COCKLEBUR 0 0 0 0 0 0 2G 0 0 0 1H 2H PURPLE NUTSEDGE 0 9G 10E 10E 7G 0 0 0 0 0 0 0 LARGE CRABGRASS 5C,9G 3C,9H 8G 9G 10H 9H 8G 3C,9G 4C,9G 4C,9G 9H 10E BARNYARDGRASS 3C,7G 0 5G 3G 5C,9H 3C,6G 2C,8H 5G 5H 3C,8G 6C,9H 7C,9H WILD OATS 0 0 0 0 0 0 0 0 0 0 0 7G ERA WHEAT 0 0 0 0 7G 0 0 0 0 0 0 8G G4646 CORN 3G 0 2G 0 2G 0 0 0 0 2G 0 2C,3H WILLMS SOYBEANS 0 0 0 0 0 0 4G 0 0 0 2G 7G RICE DRY SEEDED 0 0 2G 0 0 0 2G 0 0 0 0 1C G522 SORGHUM 2H 0 0 0 9G 0 5G 1H 0 0 7G 9H CHEAT GRASS  0 0 0 8G 4G 0    0 8G USN11 SUGARBEET 7H 0 6G 0 7H 3H 7G 5H 2H 4H 5H 9H VELVETLEAF  9C 6G 5G 2G 7G 3G 2G 7G 5G 5C,8G 8H 9H GIANT FOXTAIL 2C,9G 0 9H 6G 9H 5C,9H 9H 3C,9H 3C,9H 3C,9G 9H 9H KLAGES BARLEY 0 0 0 0 0 0 0 0 0 0 0 0 DOWNY BROME 4G       0 0 3G    CMPD 35 CMPD 35 CMPD 35 CMPD 35 CMPD 39 CMPD 42 CMPD 47 CMPD 51 CMPD 52   RATE = KG/HA 2 0.4 0.4 0.4 0.4 0.4 0.4 2 2 COKER COTTON 9G  0 8G 0 0 0 5G 9G CULT MORNINGLRY 3C,9H 8G 0 6G 0 0 0 9H 5C,9Z COCKLEBUR 0 0 0 0 0 0 1C,2G 2C,8G PURPLE NUTSEDGE 3G 0 0 0 0 0 0 0 5G LARGE CRABGRASS 10H 3C,9G 0 3C,9G 6G 2C,9G 9G 10H 9H BARNYARDGRASS 9H 7H 0 3C,9G 2G 0 1H 3C,9H 9H WILD OATS 8G 0 0 2G 0 2G 0 2G 2C,8G ERA WHEAT 5G 0 0 0 0 0 0 0 4C,9G G4646 CORN 3G 0 0 0 0 0 3G 0 3C,6G WILLMS SOYBEANS 2C,9G 0 0 9G 0 0 0 0 9G,5I RICE DRY SEEDED 0 0 0 4G 0 0 0 0 8G G522 SORGHUM 2C,9G 0 0 5G 0 0 0 2C,9G 9G CHEAT GRASS 8G   5G 0 0 0 3G 9G USN11 SUGARBEET 9G 3H 0 5H 2H 5H 4H 9H 9G VELVETLEAF 9G 5C,9G 0 7G 0 0 0 9H 9G GIANT FOXTAIL 9H 9H 0 3C,9G 6G 3C,9G 3C,9H 3C,9H 10H KLAGES BARLEY 0 0 0 0 0 0 0 0 7G DOWNY BROME  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 diamater by 12.5 cm deep) were filled with Sassafras sandy loam soil. One pan was planted with nutsedge tubers, crabgrass, sicklepad, 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 rates for plant response. 
     Response ratings were based on a scale of 0 to 100 where 0=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 52RATE = G/HA 0250          0125             0062                2000                   1000                      0500                         0250                            0500                               0250                                  2000                                     1000                                        0250                                           0062                                              2000                                                 1000                                                    0250                                                       0062__________________________________________________________________________POSTGIANT FOXTAIL       -- 0  0  -- 50 30 0  100                               90 -- 80 70 30 -- 70 50 30VELVETLEAF  30 0  0  80 50 30 0  100                               70 100                                     90 70 50 90 70 50 30USH11 SUGARBEET       -- 30 0  -- 80 70 50 70 50 -- 70 60 50 -- 70 50 30LARGE CRABGRASS        0 0  0  80 70 50 30 100                               50 100                                     100                                        90 30 100                                                 90 90 50PRICKLY SIDA       30 0  0  90 70 50 30 100                               90 100                                     90 70 50 90 80 70 50JIMSONWEED   0 0  0  60 40 20 0  60 20 90 70 50  0 90 70 50 30RICE DRY SEEDED        0 0  0   0  0  0 0  30 10 60 30  0  0 60 40  0 0COCKLEBUR   30 0  0  60 30  0 0  30 -- 90 70 50 30 90 60 30 0COKER COTTON       20 0  0  70 50 30 0  90 70 50 40 30 20 50 40 30 0WILLMS SOYBEANS       -- 0  0  -- 40  0 0  80 60 -- 80 60 20 -- 30  0 0BARNYARDGRASS       0  0  0  70 50 30 0  100                               80 80 60 30  0 90 60 30 0WILD OATS   -- 0  0  --  0  0 0  50  0 -- 30  0  0 -- 30  0 0IVY MORNINGLORY       30 0  0  100                   70 50 30 20  0 70 60 50 30 90 70 50 30ERA WHEAT   -- 0  0  --  0  0 0  10  0 --  0  0  0 -- 50 30 0SICKLEPOD   0  0  0  80 30  0 0  50 30 90 70 50 30 70 40 30 0JOHNSONGRASS       0  0  0  30  0  0 0  100                               100                                  90 70 50 30 90 70 50 0PURPLE NUTSEDGE       0  0  0  30  0  0 0  80 -- 30  0  0  0 50 30  0 0G4646 CORN  -- 0  0  --  0  0 0   0  0 -- 40  0  0 -- 40  0 0WILD BUCKWHEAT       -- 0  0  -- 70 60 50 --  0 -- 70 50 30 -- 70 50 30BLACKGRASS  -- 0  0  -- 50 30 0  90 60 -- 50 30  0 -- 70 50 30ALTEX RAPE  -- 0  0  -- 50 30 0  80 60 -- 80 50 30 -- 50 30 0KLAGES BARLEY       -- 0  0  --  0  0 0   0  0 --  0  0  0 -- 30  0 0GREEN FOXTAIL       30 0  0  80 50 30 0  100                               90 90 80 60 30 90 70 50 30CHEAT GRASS -- 0  0  --  0  0 0        --  0  0  0 -- 50 30 0FIELD VIOLET       -- 0  0  --  0  0 0        --  0  0  0 -- 50 30 0LAMBSQUARTER       70 60 50 90 80 70 60 100                               80 100                                     100                                        70 50 90 80 70 50CHICKWEED SPP.                   80 20DOWNY BROME                      40 20__________________________________________________________________________       CMPD 18             CMPD 35                   CMPD 33  CMP 35      CMPD 1381                                                 CMPD 1304RATE = G/HA 0500          0250             0250  0500                      0250                         0125                            0500                               0250                                  0125                                     0062                                        0250                                           0125                                              0062                                                 0250                                                    0125                                                       0062__________________________________________________________________________POSTGIANT FOXTAIL       30  0 80    30  0  0  0  0  0 -- 60 30  0  0  0  0VELVETLEAF  80 50 70    90 70 60 90 70 50 30  0  0  0 100                                                    70 30USH11 SUGARBEET       60 50 60    90 80 70 50 30  0 -- 70 50 30 30  0  0LARGE CRABGRASS       30 20 80    70 60 50 70 60 50 30  0  0  0  0  0  0PRICKLY SIDA       70 50 80    70 60 50 90 60 30  0  0  0  0 50 30  0JIMSONWEED  40  0 50    90 70 50 30 20  0  0 60 50 30 60 30  0RICE DRY SEEDED       40 30  0     0  0  0  0  0  0  0  0  0  0  0  0  0COCKLEBUR   40 20 30    30 20  0 30  0  0  0 50 30  0 50 30  0COKER COTTON       60 40 90    30 30 30 60 40 30  0 50 30  0 50 30  0WILLMS SOYBEANS       30 30 30    60 50 40 60 40 30 -- 30  0  0 30  0  0BARNYARDGRASS       10 10 90     0  0  0  0  0  0  0  0  0  0  0  0  0WILD OATS   30  0  0    30  0  0  0  0  0 --  0  0  0  0  0  0IVY MORNINGLORY       30 20 70    80 70 50 50 30  0  0 50 30  0 30  0  0ERA WHEAT    0  0  0     0  0  0  0  0  0 --  0  0  0  0  0  0SICKLEPOD   40 20 20    50 30 20 50 30  0  0 30  0  0 50 30  0JOHNSONGRASS       40  0 90     0  0  0 50 30  0  0 30  0  0  0  0  0PURPLE NUTSEDGE       30  0  0     0  0  0 60 30  0  0 30  0  0 70 50 30G4646 CORN   0  0  0     0  0  0  0  0  0 --  0  0  0  0  0  0WILD BUCKWHEAT       40 -- 50    60 30  0 80 50 30 -- 50 30  0 60 30  0BLACKGRASS  40  0 40    30  0  0 50 30  0 -- 70 50 30 30  0  0ALTEX RAPE  100          80 50    70 50 30 30  0  0 -- 30  0  0  0  0  0KLAGES BARLEY       10  0  0     0  0  0  0  0  0 --  0  0  0  0  0  0GREEN FOXTAIL       40  0 80    30  0  0 50 30  0  0 30  0  0  0  0  0CHEAT GRASS 30 10        0  0  0  0  0  0 --  0  0  0FIELD VIOLET            90 60 30LAMBSQUARTER       100          50 60    80 70 50 50 30  0  0  0  0  0 80 50  0CHICKWEED SPP.       50  0  0             60 30  0 --  0  0  0 60 30  0DOWNY BROME        0                                   0  0  0__________________________________________________________________________                      CMPD 810    CMPD 9   CMPD 107 CMPD 13          RATE = G/HA 0500                         0250                            0125                               0062                                  0500                                     0250                                        0125                                           0500                                              0250                                                 0125                                                    0250                                                       0125__________________________________________________________________________          POST          GIANT FOXTAIL                      80 20  0  0 80 50 30 60 20  0 20  0          VELVETLEAF  60 30 20  0 70 40 -- 80 80 70 70 60          USH11 SUGARBEET                      20 20  0 -- 90 50 40 90 90 80 80 40          LARGE CRABGRASS                      40 20  0  0 30 20  0 30 30 --  0  0          PRICKLY SIDA                      30 20  0  0 70 60 30 100                                              90 80 60 40          JIMSONWEED  30 20  0  0 50 30 30 90 50 30 40 30          RICE DRY SEEDED                      30  0  0  0 30  0  0 10  0  0  0  0          COCKLEBUR   30 20  0  0 40 40 30 50 40 20 30  0          COKER COTTON                      30 20 10 10 80 60 30 90 70 60 90 80          WILLMS SOYBEANS                      80 30  0  0 30 20  0 -- 60  0 40  0          BARNYARDGRASS                      30 20  0  0 100                                     90 30 100                                              80 70 20  0          WILD OATS   30 20  0 -- 30 20 10 20 20 -- 30  0          IVY MORNINGLORY                       0  0  0  0 50 --  0 100                                              90 60 70 40          ERA WHEAT   20  0  0  0  0  0  0  0  0  0 10  0          SICKLEPOD   20  0  0  0 70 60 60 90 40 20 40 20          JOHNSONGRASS                      20  0  0  0 50 30  0  0  0  0  0   0          PURPLE NUTSEDGE                       0  0  0  0 --  0  0 70 70  0  0  0          G4646 CORN  30 20  0  0  0  0  0  0  0  0  0  0          WILD BUCKWHEAT                      60 20  0 -- 60 40 30 90 70 70 50 30          BLACKGRASS  80 30 20 -- 70 10  0 70 40  0 80 30          ALTEX RAPE  80 30 20 -- 60 40  0 70 60 60 30  0          KLAGES BARLEY                      30 20  0 --  0  0  0  0  0  0  0  0          GREEN FOXTAIL                      30 20  0  0 100                                     70 30 80 40 30 40  0          CHEAT GRASS  0  0  0 --          LAMBSQUARTER                      80 70 30  0 -- 90 50 80 80 60 50 --          CHICKWEED SPP.                      80 20  0 -- 70 70 30 80 50 40 50  0          DOWNY BROME              0  0  0  0  0  0  0  0__________________________________________________________________________         CMPD 51         CMPD 669      CMPD 35RATE = G/HA  1000           0500               0250                  0125                      0062                         2000                             1000                                0500                                    0250                                       0500                                           0125                                              2000                                                 1000                                                    0250                                                       0062__________________________________________________________________________PREGIANT FOXTAIL        100           100 90 60  30 100 100                                100 100                                       100 100                                              100                                                 100                                                    100                                                       90VELVETLEAF   80 50  30  0   0 50  30  0   0 100 90 90 80 70 60USH11 SUGARBEET        80 70  60 50  30 70  50 30   0 90  20 60 40 30  0LARGE CRABGRASS        100           90  70 50  30 100 100                                90  80 100 100                                              100                                                 100                                                    100                                                       100PRICKLY SIDA 90 80  70 50  30 90  70 50  30 100 100                                              90 80 70 60JIMSONWEED   80 60  40 30   0 70  50 40  30 70  50 100                                                 90 80 60RICE DRY SEEDED         0  0   0  0   0  0   0  0    0                                       10   0  0  0  0  0COCKLEBUR    50 30   0  0   0 40  20  0   0 20   0 50 40 30  0COKER COTTON  0  0   0  0   0  0   0  0   0 100 20 80 70 60 30WILLMS SOYBEANS         0  0   0  0   0  0   0  0   0 10   0 90 80 30  0BARNYARDGRASS        100           80  50 30   0 100 100                                50  30 100 60 100                                                 100                                                    100                                                       60WILD OATS     0  0   0  0   0  0   0  0   0 40  20  0  0  0  0IVY MORNINGLORY         0  0   0  0   0 40   0  0   0  0   0 80 60 40  0ERA WHEAT     0  0   0  0   0  0   0  0   0 20   0  0  0                                                        0SICKLEPOD    60 30   0  0   0 30   0  0   0 50   0 90 70 30  0JOHNSONGRASS 90 70  50 30   0 90  80 50  30 100 50 100                                                 100                                                    90 70PURPLE NUTSEDGE         0  0   0  0   0  0   0  0   0 50   0  0  0  0  0G4646 CORN    0  0   0  0   0  0   0  0   0 40  10 60 40 20  0WILD BUCKWHEAT        60 30   0  0   0 70  50 30   0 100 30 80 70 50 30BLACKGRASS   60 30   0  0   0 70  50 30   0 100 80 90 80 60 30ALTEX RAPE   70 60  50 30   0 70  50 30   0 80  40 90 70 50 30KLAGES BARLEY         0  0   0  0   0  0   0  0   0  0   0  0  0  0  0GREEN FOXTAIL        100           100 90 70  50 100 100                                100 100                                       100 100                                              100                                                 100                                                    100                                                       100CHEAT GRASS   0  0   0  0   0 30   0  0   0        60 30  0  0FIELD VIOLET 90 70  50 30   0 80  30  0   0        80 70 50 30LAMBSQUARTER 100           100 90 80  70 100 90 70  50 100 90 100                                                 100                                                    90 80CHICKWEED SPP.                              40  --DOWNY BROME                                 80  40__________________________________________________________________________        CMPD 52       CMPD 18       CMPD 35    CMPD 33RATE = G/HA  2000           1000               0250                   0062                      0500                          0250                             0125                                 0062                                    0250                                        0125                                           0062                                               0500                                                  0250                                                      0125__________________________________________________________________________PREGIANT FOXTAIL        100           100 90  60 100 100                             90  30 100 100                                           100 100                                                  90  80VELVETLEAF   90 70  50  30 70  20 --  -- --  90 30  90 80  70USH11 SUGARBEET        80 50  30   0 50  30 20  -- 50  20  0  80 50  30LARGE CRABGRASS        100           100 100 80 100 100                             100 50 100 100                                           60  90 70  50PRICKLY SIDA 90 80  80  70 90  90 80  50 --  70 60  60 30   0JIMSONWEED   100           100 70  50 70  20  0   0  0   0  0  70 50  30RICE DRY SEEDED        50 30   0   0 10   0  0  30 30  10  0   0  0   0COCKLEBUR    100           100 50  30 20   0  0  30  0  --  0  30  0   0COKER COTTON 80 60  20   0 10   0  0  -- 50  20  0  30  0   0WILLMS SOYBEANS        80 60   0   0 10   0  0   0 40  10  0   0  0   0BARNYARDGRASS        100           100 80  30 100 60 20   0 80  30 10  100                                                  90  80WILD OATS    30 20   0   0 30   0 --  -- 10   0  0   0  0   0IVY MORNINGLORY        80 60  40   0 40  30 30   0 50  40 40  60 40  20ERA WHEAT    50 30   0   0 10   0  0   0  0  --  0   0  0   0SICKLEPOD    90 60  30   0 100 50 30   0 90  40 30  50 30   0JOHNSONGRASS 100           90  80  50 90  60 30   0 70  10  0  50 30   0PURPLE NUTSEDGE        70 30   0   0                0   0  0   0  0   0G4646 CORN   60 30   0   0 10  10 10   0  0   0  0   0  0   0WILD BUCKWHEAT        80 50  30   0 50  30 30   0 40   0 --   0  0   0BLACKGRASS   90 70  50  30 90  80 80  30 50  -- 10  30  0   0ALTEX RAPE   70 40  20   0 30  20 20  -- 40  40 30  90 80  70KLAGES BARLEY        30 20   0   0 30  30 20  10 10   0  0   0  0   0GREEN FOXTAIL        100           100 90  70 100 100                             100 30 100 100                                           70  100                                                  90  80CHEAT GRASS  70 50  30   0 40  20 20  20             0  0   0FIELD VIOLET 100           90  30   0                          70 50  30LAMBSQUARTER 100           100 90  80 100 90 80  60 100 70 60  100                                                  100 100CHICKWEED SPP.             50  20 --  -- 40  30  0DOWNY BROME                              30  10  0__________________________________________________________________________        CMPD 35       CMPD 1381 CMPD 1304  CMPD 810RATE = G/HA  0500           0250               0125                   0062                      0250                          0125                             0062                                0250                                    0125                                       0062                                           0500                                               0250                                                  0125                                                      0062__________________________________________________________________________PREGIANT FOXTAIL        100           100 100 90 100 100                             90 100 100                                       70VELVETLEAF   90 80  60  50  0   0  0 30   0  0  50  40 20   0USH11 SUGARBEET        70 50  40   0 90  70 50 50  30  0  40  30 30  20LARGE CRABGRASS        100           100 100 100                      100 100                             100                                100 90 80  100 90 90  20PRICKLY SIDA 70 60  60  50 30   0  0 70  50 30  60  50 30  20JIMSONWEED   40 40  20   0 50  30  0 30   0  0  50  40 30  30RICE DRY SEEDED        10 10   0   0  0   0  0  0   0  0   0   0  0   0COCKLEBUR    30 30   0   0 50  30  0 50  30  0  30  20  0   0COKER COTTON 60 10   0   0 30  30 30  0   0  0   0   0  0   0WILLMS SOYBEANS        10 10   0   0  0   0  0  0   0  0  20   0  0   0BARNYARDGRASS        100           90  40  30 80  50 30 70  30  0  100 90 70  40WILD OATS    40 30  20   0 50  30  0 50  30  0  20   0  0   0IVY MORNINGLORY        20  0   0   0 60  30  0  0   0  0  30  20  0   0ERA WHEAT    20 20  10   0 30   0  0 30   0  0  20   0  0   0SICKLEPOD    30 20   0   0  0   0  0  0   0  0   0   0  0   0JOHNSONGRASS 90 80  40  40 70  30  0 40   0  0  50  40 30  20PURPLE NUTSEDGE        100           20   0   0 30   0  0  0   0  0   0   0  0   0G4646 CORN    0  0   0   0  0   0  0  0   0  0  30  20  0   0WILD BUCKWHEAT        50 30   0   0  0   0  0 70  50 30  30   0  0   0BLACKGRASS   60 40  40  30 50  40 30 50  30  0  70  30 20   0ALTEX RAPE   80 80  70  30 70  50 30  0   0  0  30  20  0   0KLAGES BARLEY        20  0   0   0  0   0  0  0   0  0  30   0  0   0GREEN FOXTAIL        100           100 100 60 100 100                             80 100 100                                       70  100 100                                                  100 90CHEAT GRASS  40 30   0   0 30   0  0            40  30 20   0LAMBSQUARTER 100           90  80  80 70  50 30 50  30  0  90  80 50  40CHICKWEED SPP.        30  0   0   0 70  50 30  0   0  0  30   0  0   0DOWNY BROME                           0   0  0__________________________________________________________________________                      CMPD 9        CMPD 107    CMPD 13          RATE = G/HA 0500                          0250                             0125                                 0062                                    0500                                       0250                                          0125                                             0062                                                0250                                                    0125                                                       0062__________________________________________________________________________          PRE          GIANT FOXTAIL                      100 100                             100 40 100                                       100                                          90 70 100 90 40          VELVETLEAF  100 70 40  20 80 40 30 20 40  20  0          USH11 SUGARBEET                      90  70 60  40 90 80 60 10 90  80 50          LARGE CRABGRASS                      100 100                             100 100                                    100                                       100                                          100                                             100                                                100 100                                                       100          PRICKLY SIDA                      90  50 10   0 80 80 70  0 90  60 40          JIMSONWEED  80  50 30  30 50 40 20  0 50  30  0          RICE DRY SEEDED                       0   0  0   0  0  0  0  0  0   0  0          COCKLEBUR   30   0  0   0 10  0  0  0 20   0  0          COKER COTTON                      30  10 --   0 10  0  0  0  0   0  0          WILLMS SOYBEANS                      10   0  0   0  0  0  0  0  0   0  0          BARNYARDGRASS                      100 100                             30   0 100                                       90 40  0 90  40  0          WILD OATS    0   0  0   0 30  0  0  0  0   0  0          IVY MORNINGLORY                      20   0  0   0 50 30  0  0  0   0  0          ERA WHEAT    0   0  0   0  0  0  0  0 20   0  0          SICKLEPOD   50  20  0   0 80 40 --  0 30   0  0          JOHNSONGRASS                      100 90 50  40 100                                       90 40 20 60  50 30          PURPLE NUTSEDGE                       0   0  0   0 30 --  0  0  0   0  0          G4646 CORN  10   0  0   0 10  0  0  0  0   0  0          WILD BUCKWHEAT                      80  50 30   0 70 60 50 20 80  40 30          BLACKGRASS  90  50 20   0 70 50 30 10 40  30 10          ALTEX RAPE  90  70 50  30 70 60 60 40 70  60 50          KLAGES BARLEY                       0   0  0   0  0  0  0  0  0   0  0          GREEN FOXTAIL                      100 100                             100 40 100                                       100                                          100                                             90 100 50 20          LAMBSQUARTER                      100 100                             90  80 100                                       90 90 80 100 90 80          CHICKWEED SPP.                      40  10  0   0 70 40  0  0 30   0  0          DOWNY BROME 40  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 (Scripus 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 platings 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 broadleaf 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 postmergence with the test chemicals dissolved in a nonpytotoxic solvent. 
     Postemergence 
     Preemergence plantings were grown in fertilized Tama slit 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 50         RATE 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    0POSTEMERGENCEG4646 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 33          RATE 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        0POSTEMERGENCEG4646 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 35         RATE 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     0POSTEMERGENCEG4646 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 sestivum cv. Park), barley (Hordeum vulgare cv. Bonansa), 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 (Polygonium 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 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         RATE GM/HA         0500  0250     0125    0064______________________________________POSTEMERGENCEPARK WHEAT      0       0        0     0BONANZA BARLEY  0       0        0     0BLACK NIGHTSHAD 60      40       0     0CMN CHICKWEED   0       0        0     0LAMBSQUARTER    40      20       0     0CTCHWD BEDSTRAW 50      0        0     0KOCHIA          0       0        0     0SNTLS CHAMOMILE 60      40       20    0REDROOT PIGWEED 90      60       50    30PERSN SPEEDWELL 40      20       0     0WILD BUCKWHEAT  0       0        0     0MUSTARD SPP.    30      30       30    0WILD RADISH     60      30       30    0ANN. BLUEGRASS  50      20       0     0ITALN. RYEGRASS 0       20       20    0BLACKGRASS      0       0        0     0GREEN FOXTAIL   0       0        0     0WILD OATS       0       0        0     0JET RAPE        20      0        0     0PREEMERGENCEPARK WHEAT      0BONANZA BARLEY  30BLACK NIGHTSHAD 100CMN CHICKWEED   0LAMBSQUARTER    100CTCHWD BEDSTRAW 0KOCHIA          70SNTLS CHAMOMILE 100REDROOT PIGWEED 70PERSN SPEEDWELL 20WILD BUCKWHEAT  0MUSTARD SPP.    0WILD RADISH     0ANN. BLUEGRASS  20ITALN. RYEGRASS 0BLACKGRASS      0GREEN FOXTAIL   100WILD OATS       20JET RAPE        0______________________________________ CMPD 644         RATE GM/HA         0500  0250     0125    0064______________________________________POSTEMERGENCEPARK WHEAT      40      30       20    0BONANZA BARLEY  40      20       20    0BLACK NIGHTSHAD 20      10       0     0CMN CHICKWEED   0       0        0     0LAMBSQUARTER    40      20       0     0CTCHWD BEDSTRAW 30      30       30    0KOCHIA          70      50       0     0SNTLS CHAMOMILE 90      50       50    20REDROOT PIGWEED 60      50       50    50LADY SMARTWEED  100     100      100   0PERSN SPEEDWELL 80      40       20    0WILD BUCKWHEAT  0       0        0     0MUSTARD SPP.    50      50       20    20WILD RADISH     80      50       30    20ANN. BLUEGRASS  80      50       50    20ITALN. RYEGRASS 40      50       20    0BLACKGRASS      50      30       0     0GREEN FOXTAIL   50      50       30    30WILD OATS       20      20       0     0JET RAPE        30      0        0     0PREEMERGENCEPARK WHEAT      30BONANZA BARLEY  50BLACK NIGHTSHAD 0CMN CHICKWEED   20LAMBSQUARTER    85CTCHWD BEDSTRAW 0KOCHIA          100SNTLS CHAMOMILE 100REDROOT PIGWEED 80PERSN SPEEDWELL 50WILD BUCKWHEAT  30MUSTARD SPP.    0WILD RADISH     0ANN. BLUEGRASS  80ITALN. RYEGRASS 0BLACKGRASS      20GREEN FOXTAIL   100WILD OATS       20JET RAPE        20______________________________________CMPD 52         RATE GM/HA         0500  0250     0125    0064______________________________________POSTEMERGENCEPARK WHEAT      50      40       30    30BONANZA BARLEY  40      20       20    0BLACK NIGHTSHAD 70      10       0     0CMN CHICKWEED   0       0        0     0LAMBSQUARTER    10      0        0     0CTCHWD BEDSTRAW 100     70       80    20KOCHIA          70      0        0     0SNTLS CHAMOMILE 85      50       50    20REDROOT PIGWEED 90      90       50    0PERSN SPEEDWELL 90      60       30    40WILD BUCKWHEAT  30      0        0     0MUSTARD SPP.    50      20       0     0WILD RADISH     80      50       10    10ANN. BLUEGRASS  70      60       40    30ITALN. RYEGRASS 80      50       20    0BLACKGRASS      60      20       0     0GREEN FOXTAIL   75      40       0     0WILD OATS       30      20       0     0JET RAPE        40      20       0     0______________________________________CMPD 52         RATE GM/HA         0250______________________________________PREEMERGENCEPARK WHEAT      70BONANZA BARLEY  70BLACK NIGHTSHAD 100CMN CHICKWEED   0LAMBSQUARTER    100CTCHWD BEDSTRAW 100KOCHIA          0SNTLS CHAMOMILE 100REDROOT PIGWEED 100PERSN SPEEDWELL 100WILD BUCKWHEAT  20MUSTARD SPP.    50WILD RADISH     50ANN. BLUEGRASS  100ITALN. RYEGRASS 70BLACKGRASS      20GREEN FOXTAIL   100WILD OATS       70JET RAPE        20______________________________________CMPD 4         RATE GM/HA         0500  0250     0125    0064______________________________________POSTEMERGENCEPARK WHEAT      50      30       10    0BONANZA BARLEY  60      40       30    20BLACK NIGHTSHAD 90      70       30    10CMN CHICKWEED   0       0        0     0LAMBSQUARTER    70      20       20    0CTCHWD BEDSTRAW 100     80       20    20KOCHIA          90      70       30    0SNTLS CHAMOMILE 85      70       50    30REDROOT PIGWEED 90      90       40    20PERSN SPEEDWELL 100     100      70    20WILD BUCKWHEAT  70      40       0     0MUSTARD SPP.    80      40       40    20WILD RADISH     90      80       60    20ANN. BLUEGRASS  60      40       20    0ITALN. RYEGRASS 80      30       0     0BLACKGRASS      50      20       20    0GREEN FOXTAIL   80      20       20    0WILD OATS       30      0        0     0JET RAPE        30      20       20    0PREEMERGENCEPARK WHEAT      80BONANZA BARLEY  80BLACK NIGHTSHAD 100CMN CHICKWEED   0LAMBSQUARTER    100CTCHWD BEDSTRAW 100KOCHIA          100SNTLS CHAMOMILE 100REDROOT PIGWEED 100LADY SMARTWEED  100PERSN SPEEDWELL 90WILD BUCKWHEAT  40MUSTARD SPP.    50WILD RADISH     50ANN. BLUEGRASS  100ITALN. RYEGRASS 70BLACKGRASS      90GREEN FOXTAIL   100WILD OATS       90JET RAPE        40______________________________________CMPD 107         RATE GM/HA         0250______________________________________PREEMERGENCEPARK WHEAT      30BONANZA BARLEY  30BLACK NIGHTSHAD 80CMN CHICKWEED   0LAMBSQUARTER    90CTCHWD BEDSTRAW 0KOCHIA          70SNTLS CHAMOMILE 70REDROOT PIGWEED 100PERSN SPEEDWELL 100WILD BUCKWHEAT  0MUSTARD SPP.    20WILD RADISH     60ANN. BLUEGRASS  20ITALN. RYEGRASS 0BLACKGRASS      20GREEN FOXTAIL   100WILD OATS       0JET RAPE        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 1/ha, then after 3 weeks of growth in a greenhouse, plant responses 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 4        RATE 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______________________________________