Patent Publication Number: US-5292762-A

Title: Halopropargyl compounds, compositions, uses and processes of preparation

Description:
This application is a continuation-in-part of Ser. No. 370,373 of Jun. 22, 1988. 
    
    
     BACKGROUND OF THE INVENTION 
     1. Field of the Invention 
     This invention relates to control of microorganisms. 
     2. Description of the Prior Art 
     Certain classes of iodopropargyl compounds have been proposed as fungicides or microbicides but no compound within those classes has achieved commercial success. 
     U.S. Pat. No. 4,616,004 to Edwards discloses fungicidal activity for compounds of the formula ##STR2## 
     U.S. Pat. No. 4,639,460 to Rose shows compounds of the formula ##STR3## as fungicides. 
     U.S. Pat. No. 4,520,023 to Schmitt shows 3-(3-iodopropargyl)benzo-1,2,3-triazolin-4-ones and their use as microbicidal agents. 
     There was no suggestion in the prior art that compounds within the formula of the present invention would have utility in controlling microorganisms. 
     SUMMARY OF THE INVENTION 
     It is an object of the present invention to provide new compounds for controlling microorganisms. 
     A further object is to provide methods of making such compounds, methods of using them, compositions comprising such compounds, and uses of such compositions. 
     These objects, and others which will become apparent from the following disclosure, are achieved by the present invention which comprises in one aspect compounds of the formula ##STR4## wherein A is selected from the group consisting of hydrogen, alkyl, aryl, and heterocyclic; 
     Y and Z are independently selected from the group consisting of O, S, and N--R, 
     R is selected from the group consisting of hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted phenyl, and substituted or unsubstituted heterocyclic; and 
     X is selected from the group consisting of I and Br. 
     In another aspect the invention comprises a method of preparing such compound comprising reacting compound of the formula ##STR5## with an iodinating or brominating agent. 
     A further aspect comprises using a composition comprising the compounds, or the compound itself, to protect a material selected from the group consisting of wood, paint, adhesive, glue, paper, textile, leather, plastics, cardboard, lubricants, cosmetics, food, caulking, feed and industrial cooling water from microorganisms. 
    
    
     DETAILED DESCRIPTION OF THE INVENTION AND THE PREFERRED EMBODIMENT 
     The compounds of the invention are of formula I as set forth above. The more preferred embodiments are those wherein A is selected from the group consisting of hydrogen; (C 1  to C 18 ) straight or branched alkyl; (C 3  to C 8 ) cycloalkyl; (C 3  to C 6 ) alkenyl; (C 3  to C 5 ) alkynyl; (C 7  to C 12 ) aralkyl; (C 6  to C 12 ) aryl; (C 6  to C 12 ) aryl substituted with 1 to 3 substituents selected from the group consisting of halogen, (C 1  to C 4 ) alkyl, (C 1  to C 4 ) alkoxy, nitro, cyano, carboxyl (C 1  to C 4 ) alkoxycarbonyl, (C 1  to C 4 ) alkyl thio, -S(O)nR 2  where n is 1 or 2 and R 2  is (C 1  -C 4 ) alkyl; and a halo-substituted, nitro-substituted, or un-substituted moiety selected from the group consisting of 2-thienyl, 3-thienyl, 2-furyl, 3-furyl, 2-pyridyl, 3-pyridyl, and 4-pyridyl. A cannot be R 4  S- where R 4  is any moiety. Examples of heterocyclic R substituents are furyl, thienyl, pyridyl, and the like. 
     The iodopropargyl compounds, i.e., those wherein X is I, are preferred. The 5-one compounds, i.e., those wherein Y is O, are also preferred. 
     As stated above, compositions comprising a compound according to formula I and either an agronomically acceptable carrier, a cosmetic agent, a cutting oil, a soap or synthetic detergent, a stabilizer, a film forming material, or the like have a wide range of utility for protecting against or controlling microorganisms from a wide variety of classes including fungus, bacteria, algae, viruses and yeasts. The preferred utilities of the compositions are to protect wood, paint, adhesive, glue, paper, textile, leather, plastics, cardboard, lubricants, cosmetics, food, caulking, feed and industrial cooling water from microorganisms. 
     The following lists specific industries and applications of the compounds or compositions. 
     
         ______________________________________                                    
Industry       Application                                                
______________________________________                                    
Adhesives, Sealants                                                       
               Adhesives                                                  
               Caulks                                                     
               sealants                                                   
agriculture/food chain                                                    
               adjuvant preservation                                      
               agricultural active ingredient                             
               agricultural chemical preservative                         
               agricultural formulations preservation                     
               animal feed preservation                                   
               dairy chemicals                                            
               fertilizer preservation                                    
               food preservation                                          
               food processing chemicals                                  
               grain preservation                                         
               post-harvest produce protection                            
               sugar processing                                           
               tobacco                                                    
Construction products                                                     
               asphalt/concrete                                           
               cement modifiers                                           
               construction products                                      
               roof mastics                                               
               synthetic stucco                                           
               wall mastics                                               
               joint cement                                               
Cosmetics and toiletries                                                  
               Cosmetics                                                  
               raw materials for cosmetics, toiletries                    
               toiletries                                                 
Disinfectants, antiseptics                                                
               antiseptic                                                 
               disinfectant                                               
Emulsions, dispersions                                                    
               aqueous dispersions                                        
               dispersed pigments                                         
               latex                                                      
               photographic emulsions                                     
               pigment slurries                                           
               polymer latices                                            
formulated household                                                      
               fabric softeners                                           
products       polishes                                                   
               waxes                                                      
               hand dish detergents                                       
               raw materials                                              
               liquid detergents                                          
               hand soaps                                                 
Industrial processing, misc                                               
               electrodeposition paint, baths, rinses.                    
               electrodeposition pre-treatment, post                      
               rinses                                                     
               Industrial fluids preservation                             
               pasteurization baths                                       
               process aid preservation                                   
Industrial water treatment                                                
               air washers                                                
               cooling towers                                             
               cooling water                                              
               water cooling                                              
               preservation/treatment of wooden                           
               cooling tower slats and structural                         
               members                                                    
               can warmers                                                
               brewery pasteurization                                     
               closed loop water cooling systems                          
Laundry        household laundry products                                 
               laundered goods                                            
               laundry wash water                                         
               sanitizers-laundry                                         
Leather, Leather products                                                 
               leather and hide                                           
               leather and hide products                                  
Lubricants, hydraulic aids                                                
               automotive lubricants and fluids                           
               conveyor lubricants                                        
               greases                                                    
               hydraulic fluids                                           
               lubricants                                                 
Medical devices                                                           
               diagnostic enzymes                                         
               diagnostic kits                                            
               medical devices                                            
metalworking &amp; related                                                    
               cutting fluids                                             
app&#39;s          Metal cleaning                                             
               metalworking fluids                                        
Odor control (active                                                      
               air conditioning                                           
ingredient)    animal bedding                                             
               cat litter                                                 
               chemical toilet prep&#39;ns                                    
               deodorizers                                                
               humidifiers                                                
               industrial deodorants                                      
               sanitary formulations                                      
               toilet bowls                                               
Paints and coatings coating                                               
               emulsions                                                  
               paints                                                     
Paper and wood pulp,                                                      
               absorbant materials of paper and                           
their products wood pulp                                                  
               packaging materials of paper and                           
               wood pulp                                                  
               paper products                                             
               paper treatment                                            
               soap wrap                                                  
               wood pulp                                                  
               wood pulp products                                         
paper mill     paper mill slimicides                                      
               pulp and paper slurries                                    
Petroleum refining, fuels                                                 
               aviation fuels (jet fuel, aviation gas)                    
               crude oils                                                 
               burner, diesel and turbine fuel oils                       
               coal slurries                                              
               diesel fuel additives                                      
               diesel fuels                                               
               fuels                                                      
               gasoline                                                   
               heating oils                                               
               hydrocarbons                                               
               Kerosene                                                   
               liquefied petroleum gas                                    
               petrochemical feedstocks                                   
               petroleum products, storage,                               
               transportation and production                              
               recycled petroleum products                                
               residual fuel oils                                         
               turbine oils                                               
Photographic Chemicals                                                    
               Photographic processing - wash                             
and process    water, rinses                                              
               photoprocessing                                            
               Photoplate processing chemicals                            
               (developers, stabilizers etc)                              
Printing       Fountain solutions (printing)                              
               Ink components (pigments, resins,                          
               solvents, etc)                                             
               Inks                                                       
sanitizers (active)                                                       
               sanitizers                                                 
               sanitizers-dairy                                           
               sanitizers-dental                                          
               sanitizers-fermentation                                    
               sanitizers-food preparation                                
               sanitizers-food processing                                 
               sanitizers-medical                                         
               sanitizers-rendering                                       
               sanitizers-veterinary                                      
Soaps, detergents, cleaners                                               
               cleaners                                                   
               detergents                                                 
               household cleaners                                         
               industrial cleaners                                        
               liquid soaps                                               
               oil and grease remover                                     
               powdered soaps                                             
               raw materials for cleaning products                        
               soaps                                                      
               surfactants                                                
Textiles, textile products                                                
               bonded fabrics                                             
               burlap                                                     
               canvas                                                     
               canvas goods                                               
               carpet backing                                             
               carpets                                                    
               clothing                                                   
               coated fabrics                                             
               curtains                                                   
               draperies                                                  
               engineering textiles                                       
               fibers                                                     
               geotextiles                                                
               goods made of textiles                                     
               knitted fabrics                                            
               nets                                                       
               nonwoven fabrics                                           
               rope                                                       
               rugs                                                       
               textile accessories                                        
               textile products                                           
               textiles                                                   
               upholstery                                                 
               woven fabrics                                              
               yarn                                                       
Textile processing                                                        
               dye fixatives                                              
               dyes                                                       
               fiber lubricants                                           
               hand modifiers                                             
               sizes                                                      
               Textile processing fluids                                  
Therapeutic (active or                                                    
               animal health/veterinary                                   
preservative)  aquaculture                                                
               dental                                                     
               human health                                               
               pharmaceutical/therapeutic                                 
water purification                                                        
               charcoal beds                                              
               deionization resins                                        
               filters                                                    
               membranes                                                  
               reverse osmosis membranes                                  
               ultrafilters                                               
               Water purification                                         
               water purificiation pipes, tubing                          
wood applications                                                         
               lazures (wood stains)                                      
               wood                                                       
               wood products                                              
Miscellaneous  alcohols                                                   
               bedding incorporating water or gels                        
               ceramic                                                    
               contact lens cases-leaching                                
               electronic circuitry                                       
               electronics chemicals                                      
               enzymes-food production                                    
               enzymes                                                    
               enzymes-industrial                                         
               gel cushions                                               
               marine antifoulants                                        
               mildewcides                                                
               wood                                                       
               plastics                                                   
               laundry                                                    
               mining                                                     
               natural rubber latex                                       
               oil field injection waters including                       
               enhanced recover injection fluids,                         
               drilling, fracturing and completion                        
               fluids                                                     
               pipes                                                      
               plastics                                                   
               polymer systems                                            
               polymers and resins (synthetic and                         
               natural)                                                   
               reagent preservation                                       
               rubber                                                     
               rubber products                                            
               skin remover                                               
               solid protective/decorative films                          
               stains                                                     
               swimming pools                                             
               waste treatment                                            
               water beds                                                 
______________________________________                                    
 
    
     The amounts of the compound to be used depend on the application. The useful amounts for a particular application are similar to amounts used for other microbiocide compounds. 
     The compound can be used in combination with other microbicides. The term &#34;microbicide&#34; is considered equivalent to &#34;antimicrobial&#34; as used herein. 
     Compounds of formula I can be prepared by a variety of methods. One suitable method comprises reacting a compound of the formula ##STR6## with an iodinating or brominating agent. 
     Suitable iodinating or brominating agents include, for example, iodine, bromine, an iodine-amino compound such as morpholineiodine complex, morpholine-bromine complex, N-bromosuccinimide (&#34;NBS&#34;) and N-iodosuccinimide (&#34;NIS&#34;), the latter being the most preferred. 
     When an iodine, bromine, or iodo-amino compound is used, base should also be used, preferably sodium or potassium hydroxide, and solvent such as methanol, ethanol, and aqueous ethanol should also be used. 
     When NIS or NBS is used, a catalyst such as, for example, silver nitrate, or the like, should be used in presence of solvent such as acetone, methyl ethyl ketone, tetrahydrofuran, and the like. 
     Reaction times of about 20 minutes to about 24 hours have been utilized successfully with reaction temperatures of about 0° C. to about 25° C. 
     Suitable methods of application of compounds of formula I to control fungi, bacteria, algae, viruses, yeasts, and the like are in amounts and with carriers, etc., as well known in the art. 
     The following examples are presented to illustrate a few embodiments of the invention. All parts and percentages are by weight unless otherwise indicated. 
     EXAMPLES 
     Some representative compounds the invention are the following: 
     
         ______________________________________                                    
Com-                                                                      
pound #                                                                   
______________________________________                                    
 1.    2-(4-chlorophenyl)-4-(3-iodopropargyl)-1,3,4-                      
       oxadiazolin-5-one                                                  
 2.    2-(2-methylphenyl)-4-(3-iodopropargyl)-1,3,4-                      
       oxadiazolin-5-one                                                  
3.     2-(4-methylphenyl)-4-(3-iodopropargyl)-1,3,4-                      
       oxadiazolin-5-one                                                  
4.     2-(3-methylphenyl)-4-(3-iodopropargyl)-1,3,4-                      
       oxadiazolin-5-one                                                  
5.     2-(2-chlorophenyl)-4-(3-iodopropargyl)-1,3,4-                      
       oxadiazolin-5-one                                                  
6.     2-(3-chlorophenyl)-4-(3-iodopropargyl)-1,3,4-                      
       oxadiazolin-5-one                                                  
7.     2-(2-thienyl)-4-(3-iodopropargyl)-1,3,4-oxadiazolin-5-one          
8.     2-n-propyl-4-(3-iodopropargyl)-1,3,4-oxadiazolin-5-one             
9.     2-(4-nitrophenyl)-4-(3-iodopropargyl)-1,3,4-oxadiazolin-           
       5-one                                                              
10.    2-(3-nitrophenyl)-4-(3-iodopropargyl)-1,3,4-oxadiazolin-           
       5-one                                                              
11.    2-(2-nitrophenyl)-4-(3-iodopropargyl)-1,3,4-oxadiazolin-           
       5-one                                                              
12.    2-(4-trifluoromethylphenyl)-4-(3-iodopropargyl)-1,3,4-             
       oxadiazolin-5-one                                                  
13.    2-(2-methoxyphenyl)-4-(3-iodopropargyl)-1,3,4-                     
       oxadiazolin-5-one                                                  
14.    2-(4-methoxyphenyl)-4-(3-iodopropargyl)-1,3,4-                     
       oxadiazolin-5-one                                                  
15.    2-(3-methoxyphenyl)-4-(3-iodopropargyl)-1,3,4-                     
       oxadiazolin-5-one                                                  
16.    2-(4-bromophenyl)-4-(3-iodopropargyl)-1,3,4-                       
       oxadiazolin-5-one.                                                 
17.    2-(2-fluorophenyl)-4-(3-iodopropargyl)-1,3,4-                      
       oxadiazolin-5-one                                                  
18.    2-(2-furyl)-4-(3-iodopropargyl)-1,3,4-oxadiazolin-5-one            
19.    1-(3-iodopropargyl)-3-(4-methylphenyl)-4-ethyl-1,2,4-              
       triazolin-5-one                                                    
20.    1-(3-iodopropargyl)-3-(4-chlorophenyl)-4-ethyl-1,2,4-              
       triazolin-5-one                                                    
21.    1-(3-iodopropargyl)-3-phenyl-4-ethyl-1,2,4-triazolin-5-            
       one                                                                
22.    1-(3-iodopropargyl)-3-(4-nitrophenyl)-4-ethyl-1,2,4-               
       triazolin-5-one                                                    
23.    1-(3-iodopropargyl)-3-(4-methoxyphenyl)-4-ethyl-1,2,4-             
       triazolin-5-one                                                    
24.    1-(3-iodopropargyl)-3-(2-thienyl)-4-ethyl-1,2,4,-triazolin-        
       5-one                                                              
25.    1-(3-iodopropargyl)-3-(3-methylphenyl)-4-ethyl-1,2,4-              
       triazolin-5-one                                                    
26.    1-(3-iodopropargyl)-3-(2-methylphenyl)-4-ethyl-1,2,4-              
       triazolin-5-one                                                    
27.    1-(3-iodopropargyl)-3-(3-fluorophenyl)-4-ethyl-1,2,4-              
       triazolin-5-one                                                    
28.    1-(3-iodopropargyl)-3-(1-naphthyl)-4-ethyl-1,2,4-                  
       triazolin-5-one                                                    
29.    1-(3-iodopropargyl)-3-(2-naphthyl)-4-ethyl-1,2,4-                  
       triazolin-5-one                                                    
30.    1-(3-iodopropargyl)-3-(4-bromophenyl)-4-ethyl-1,2,4-               
       triazolin-5-one                                                    
31.    1-(3-iodopropargyl)-3-(2-fluorophenyl)-4-ethyl-1,2,4-              
       triazolin-5-one                                                    
32.    1-(3-iodopropargyl)-3-(4-fluorophenyl)-4-ethyl-1,2,4-              
       triazolin-5-one                                                    
33.    1-(3-iodopropargyl)-3-(3-pyridyl)-4-ethyl-1,2,4-                   
       triazolin-5-one                                                    
34.    1-(3-iodopropargyl)-3-(2-methoxyphenyl)-4-ethyl-1,2,4-             
       triazolin-5-one                                                    
35.    1-(3-iodopropargyl)-3-(3-nitrophenyl)-4-ethyl-1,2,4-               
       triazolin-5-one                                                    
36.    1-(3-iodopropargyl)-3-(3-chlorophenyl)-4-ethyl-1,2,4-              
       triazolin-5-one                                                    
37.    1-(3-iodopropargyl)-3-(3-bromophenyl)-4-ethyl-1,2,4-               
       triazolin-5-one                                                    
38.    1-(3-iodopropargyl)-3-(3-methoxyphenyl)-4-ethyl-1,2,4-             
       triazolin-5-one                                                    
39.    1-(3-iodopropargyl)-3-(3-ethoxyphenyl)-4-ethyl-1,2,4-              
       triazolin-5-one                                                    
40.    1-(3-iodopropargyl-3-(4-methylphenyl)-4 n-butyl-1,2,4-             
       triazolin-5-one                                                    
41.    1-(3-iodopropargyl)-3-(4-methylphenyl)-4-i-propyl-1,2,4-           
       triazolin-5-one                                                    
42.    1-(3-iodopropargyl)-3-n-propyl-4-ethyl-1,2,4-triazolin-            
       5-one                                                              
43.    1-(3-iodopropargyl)-3-(4-chlorophenyl)-4-phenyl-1,2,4-             
       triazolin-5-one                                                    
44.    1-(3-iodopropargyl)-3-(2-chlorophenyl)-4-ethyl-1,2,4-              
       triazolin-5-one                                                    
45.    1-(3-iodopropargyl)-3-(4-chlorophenyl)-4-(4-                       
       chlorophenyl)-1,2,4-triazolin-5-one                                
46.    1-(3-iodopropargyl)-3-(4-chlorophenyl)-4-(4-                       
       methylphenyl)-1,2,4-triazolin-5-one                                
47.    1-(3-iodopropargyl)-3-methyl-4-phenyl-1,2,4-triazolin-             
       5-one                                                              
48.    1-(3-iodopropargyl)-3-methyl-4-(4-chlorophenyl)-1,2,4-             
       triazolin-5-one                                                    
49.    1-(3-iodopropargyl)-4-(4-chlorophenyl)-1,2,4-triazoline-           
       5-one                                                              
50.    1-(3-iodopropargyl)-4-phenyl-1,2,4-triazolin-5-one                 
51.    1-(3-iodopropargyl)-3-(4-bromophenyl)-4-methyl-1,2,4-              
       triazolin-5-one                                                    
52.    1-(3-iodopropargyl)-3-(4-chlorophenyl)-4-methyl-1,2,4-             
       triazolin-5-one                                                    
53.    1-(3-iodopropargyl)-3-(4-fluorophenyl)-4-methyl-1,2,4-             
       triazolin-5-one                                                    
54.    1-(3-iodopropargyl)-3-(3-chlorophenyl)-4-methyl-1,2,4-             
       triazolin-5-one                                                    
55.    1-(3-iodopropargyl)-3-(3-bromophenyl)-4-methyl-1,2,4-              
       triazolin-5-one                                                    
56.    1-(3-iodopropargyl)-3-(3-fluorophenyl)-4-methyl-1,2,4-             
       triazolin-5-one                                                    
57.    1-(3-iodopropargyl)-3-(2-fluorophenyl)-4-methyl-1,2,4-             
       triazolin-5-one                                                    
58.    1-(3-iodopropargyl)-3-t-butyl-4-phenyl-1,2,4-triazolin-            
       5-one                                                              
59.    2-phenyl-4-iodopropargyl-1,3,4-thiadiazolin-5-one                  
______________________________________                                    
 
    
     Table (1) shows the structures and the physical data of these representative compounds. 
     
                                           TABLE 1                                 
__________________________________________________________________________
Physical Data                                                             
 ##STR7##                               (II)                              
 ##STR8##                               (III)                             
 ##STR9##                               (IV)                              
                              NMR Chemical Shifts                         
NO.                                                                       
   Formula                                                                
        A        R     Melting Point                                      
                              (ppm)                                       
__________________________________________________________________________
 1.                                                                       
   II   4-Cl-ph  --    151-152° C.                                 
 2.                                                                       
   II   2-Me-ph  --    152-154° C.                                 
 3.                                                                       
   II   4-Me-ph  --    174-175° C.                                 
 4.                                                                       
   II   3-Me-ph  --    114-115°  C.                                
 5.                                                                       
   II   2-Cl-ph  --    104-107° C.                                 
 6.                                                                       
   II   3-Cl-ph  --    124-126° C.                                 
 7.                                                                       
   II   2-thiophene                                                       
                 --    149-151° C.                                 
 8.                                                                       
   II   n-propyl --    42-46° C.                                   
                              4.60(2H, s, CH.sub.2), 2.55                 
                              (2H, t, CH.sub.2), 1.74(2H, m               
                              CH.sub.2), 1.02(3H, t, CH.sub.3)            
 9.                                                                       
   II   4-NO.sub.2 -ph                                                    
                 --    176-178° C.                                 
10.                                                                       
   II   3-NO.sub.2 -ph                                                    
                 --    99.5-102° C.                                
   II   2-NO.sub.2 -ph                                                    
                 --    116-120° C.                                 
   II   4-CF.sub.3 -ph                                                    
                 --    144-147° C.                                 
   II   2-MeO-ph --    115-117° C.                                 
   II   4-MeO-ph --    171-173° C.                                 
   II   3-MeO-ph --    128-130° C.                                 
   II   4-Br-ph  --    159-162° C.                                 
   II   2-F-ph   --    139-142° C.                                 
   II   furyl-2  --    140-142° C.                                 
   III  4-Me-ph  Et    141-145° C.                                 
20.                                                                       
   III  4-Cl-ph  Et    115-120° C.                                 
   III  ph       Et    144-148° C.                                 
   III  4-NO.sub. 2 -ph                                                   
                 Et    184-187° C.                                 
   III  4-OMe-ph Et    oil    7.20(4H, aromatic H),                       
                              4.75(2H, s, CH.sub.2) 3.84                  
                              (3H, s, CH.sub.3), 3.75                     
                              (2H, q, CH.sub.2) 1.28                      
                              (3H, t, CH.sub.3)                           
   III  2-thiophene                                                       
                 Et    134-136° C.                                 
   III  3-Me-ph  Et    oil    7.34(4H, m, arom. H),                       
                              4.78(2H, s, CH.sub.2), 3.80                 
                              (2H, q, CH.sub.2), 2.40                     
                              (3H, s, CH.sub.3), 1.25                     
                              (3H, t, CH.sub.3)                           
   III  2-Me-ph  Et    oil    7.35(4H, m, arom. H),                       
                              4.80(2H, s, CH.sub.2), 3.56                 
                              (2H, q, CH.sub.2), 2.29                     
                              (3H, s, CH.sub.3) 1.12                      
                              (3H, t, CH.sub.3)                           
   III  2-F-ph   Et    104-107° C.                                 
   III  1-naphthyl                                                        
                 Et    148-152° C.                                 
   III  2-naphthyl                                                        
                 Et    63-70° C.                                   
30.                                                                       
   III  4-Br-ph  Et    125-126°  C.                                
   III  2-F-ph   Et    121-124° C.                                 
   III  4-F-ph   Et    108-111° C.                                 
   III  3-pyridyl                                                         
                 Et    129-131° C.                                 
   III  3-OMe-ph Et    127-130° C.                                 
   III  3-NO.sub.2 -ph                                                    
                 Et    153-158° C.                                 
   III  3-Cl-ph  Et    --     7.60(4H, m, arom. H),                       
                              4.81(2H, s, CH.sub.2), 3.85                 
                              (2H, q, CH.sub.2), 1.32                     
                              (3H, t, CH.sub.3)                           
   III  3-Br-ph  Et    --     7.80 to 7.40                                
                              (4H, m, arom. H), 4.80                      
                              (2H, s, CH.sub.2), 3.84                     
                              (2H, q, CH.sub.2), 1.30(3H, t,              
                              (CH.sub.3)                                  
   III  3-OMe-ph Et    --     7.50 to 7.00(4H, m,                         
                              arom. H), 4.80                              
                              (2H, s, CH.sub.2), 3.85(4H, m,              
                              CH.sub.3 &amp; CH.sub.2), 1.30                  
                              (3H, t, CH.sub.3)                           
   III  3-OEt-ph Et    --     7.50 to 7.00                                
                              (4H, m, arom. H), 4.80                      
                              (2H, s, CH.sub.2), 4.10                     
                              (2H, q, CH.sub.2), 3.84                     
                              (2H, q, CH.sub.2), 1.46                     
                              (3H, t, CH.sub.3), 1.26                     
                              (3H, t, CH.sub.3)                           
40.                                                                       
   III  4-Me-ph  n-Bu  --     7.40(4H, q, arom. H),                       
                              4.78(2H, s, CH.sub.2), 3.80                 
                              (2H, t, CH.sub.2), 2.44                     
                              (3H, s, CH.sub.3), 1.62                     
                              (2H, m, CH.sub.2), 1.30                     
                              (2H, m, CH.sub.2),                          
                              0.85(3H, t, CH.sub.3)                       
   III  4-Me-ph  i-pro --     7.38(4h, q, arom. H), 4.75                  
                              (2H, s, CH.sub.2), 4.26                     
                              (1H, m, CH), 2.45                           
                              (3H, s, CH.sub.3), 1.55                     
                              (6H, d, 2-CH.sub.3) 1.55                    
                              (6H, d, 2-CH.sub.3)                         
   III  n-prop   Et    89-93° C.                                   
   III  4-Cl-ph  ph    193-195° C.                                 
   III  2-Cl-ph  Et    86-89° C.                                   
   III  4-Cl-ph  4-Cl-ph                                                  
                       171-177° C.                                 
   III  4-Cl-ph  4-Me-ph                                                  
                       179-183° C.                                 
   III  Me       ph    179-182° C.                                 
   III  Me       4-Cl-ph                                                  
                       129-131° C.                                 
   III  H        4-Cl-ph                                                  
                       147-149° C.                                 
50.                                                                       
   III  H        ph    192-193° C.                                 
   III  4-Br-ph  Me    145-150° C.                                 
   III  4-Cl-ph  Me    148-152° C.                                 
   III  4-F-ph   Me    122-125° C.                                 
   III  3-Cl-ph  Me    78-82° C.                                   
   III  3-Br-ph  Me    89-94° C.                                   
   III  3-F-ph   Ne    124-129° C.                                 
   III  2-F-ph   Me    121-126° C.                                 
   III  t-Butyl  ph    170-174° C.                                 
   IV   ph       --    117-119° C.                                 
60 II   1-naphthyl                                                        
                 --    167-169° C.                                 
61 II   Me       --    90-96° C.                                   
62 II   n-C.sub.17 H.sub.35                                               
                 --    41-46° C.                                   
63 II   n-C.sub.4 H.sub.9                                                 
                 --    oil    4.60(2H, s, CH.sub.2), 2.60                 
                              (2H, t, CH.sub.2), 1.70                     
                              (2H, m, CH.sub.2), 1.42                     
                              (2H, m, CH.sub.2), 0.95                     
                              (3H, t, CH.sub.3)                           
64 II   t-C.sub.4 H.sub.9                                                 
                 --    90-93° C.                                   
65 II   3-Br-ph  --    127-129° C.                                 
66 II   4-F-ph   --    127-129° C.                                 
67 II   3-F-ph   --    127-129° C.                                 
68 II   ph       --    137-139° C.                                 
69 II   2-EtO-ph --    138-142° C.                                 
70 II   3-EtO-ph --    129-132° C.                                 
71 II   2-Cl, 4-NO.sub.2 -ph                                              
                 --    161-166° C.                                 
72 II   4-ph-ph  --    183-186° C.                                 
   II   3,5-(OMe).sub.2 -ph                                               
                 --    161-165° C.                                 
   II   2,5-(OMe).sub.2 -ph                                               
                 --    144-147° C.                                 
   II   3,4,5-(OMe).sub.3 -ph                                             
                 --    135-137° C.                                 
   II   2,5-Cl.sub.2 -ph                                                  
                 --    121-123° C.                                 
   II   n-Heptyl --    Oil    4.62(2H, s, CH.sub.2),                      
                              2.58(2H, t, CH.sub.2),                      
                              1.70(2H, m, CH.sub.2).                      
                              1.32(12H,m 4CH.sub.2),                      
                              0.90(3H, t, CH.sub.3)                       
   III  t-Bu     3-F-ph                                                   
                       151-160° C.                                 
   III  t-Bu     Me    Oil    4.72(2H, s, CH.sub.2),                      
                              3.42(3H, s, CH.sub.3),                      
                              1.40(9H, s, 3CH.sub.3)                      
80.                                                                       
   III  t-Bu     Et    Oil    4.70(2H, s, CH.sub.2),                      
                              3.88(2H, q, CH.sub.2),                      
                              1.38(12H, m, 4CH.sub.3)                     
   III  Me       Et    Oil    4.68(2H, s, CH.sub.2),                      
                              3.72(2H, q, CH.sub.2),                      
                              2.26(3H, s, CH.sub.3),                      
                              1.30(3H, t, CH.sub.3)                       
   III  n-Bu     Et    Oil    4.82(2H, s, CH.sub.2),                      
                              3.70(2H, q, CH.sub.2),                      
                              2.40(2H, t, CH.sub.2),                      
                              1.66(2H, m, CH.sub.2),                      
                              1.38(5H, m),                                
                              0.98(3H, t, CH.sub.3)                       
   III  t-Bu     3-MeO-ph                                                 
                       168-170° C.                                 
   III  n-Pr     4-Cl-ph                                                  
                       50-56° C.                                   
   III  n-Pr     ph    106-112° C.                                 
   III  t-Bu     4-Cl-ph                                                  
                       168-171° C.                                 
   III  Me       4-Me-ph                                                  
                       166-170° C.                                 
   III  Me       4-MeO-ph                                                 
                       200-203° C.                                 
   III  n-Pr     4-MeO-ph                                                 
                       Oil    7.22(4H, q, arom. H),                       
                              4.76(2H, s, CH.sub.2),                      
                              3.85(3H, s, CH.sub.3),                      
                              2.40(2H, t, CH.sub.2),                      
                              1.58(2H, m, CH.sub.2),                      
                              0.90(3H, t, CH.sub.3)                       
90.                                                                       
   III  n-Pr     3-MeO-ph                                                 
                       109-112° C.                                 
   III  n-Pr     2-MeO-ph                                                 
                       Oil    7.55-7.02(4H, m,                            
                              arom. H),                                   
                              4.78(2H, s, CH.sub.2),                      
                              3.86(3H, s, CH.sub.3),                      
                              2.32(2H, q, CH.sub.2),                      
                              1.60(2H, m, CH.sub.2),                      
                              0.90(3H, t, CH.sub.3)                       
   III  Me       n-Hexyl                                                  
                       Oil    4.70(2H, s, CH.sub.2),                      
                              3.60(2H, t, CH.sub.2),                      
                              2.26(3H, s, CH.sub.3 ),                     
                              1.64(2H, m, CH.sub.2),                      
                              1.34(6H, m, 3CH.sub.2),                     
                              0.91(3H, t, CH.sub.3)                       
   III  Me       Benzyl                                                   
                       170-172° C.                                 
   III  Me       Cyclohexyl                                               
                       103-106° C.                                 
   III  H        3-Cl-ph                                                  
                       112-115° C.                                 
   III  H        3-Me-ph                                                  
                       153-156° C.                                 
   III  H        2-Me-ph                                                  
                       132-134° C.                                 
   III  H        2-Cl-ph                                                  
                       139-140° C.                                 
   III  H        4-Me-ph                                                  
                       165-170° C.                                 
100.                                                                      
   III  H        n-Bu  66-70° C.                                   
101.                                                                      
   III  H        Et    Oil    7.42(1H, s)                                 
                              4.64(2H, s, CH.sub.2),                      
                              3.70(2H, q, CH.sub.2),                      
                              1.34(3H, t, CH.sub.3)                       
102.                                                                      
   III  H        4-F-ph                                                   
                       124-127° C.                                 
103.                                                                      
   III  H        4-MeO-ph                                                 
                       117-120° C.                                 
104.                                                                      
   III  H        4-NO.sub.2 -ph                                           
                       165-166° C.                                 
105.                                                                      
   III  H        4-Br-ph                                                  
                       175-177° C.                                 
106.                                                                      
   III  H        2,4-Cl.sub.2 -ph                                         
                       148-151° C.                                 
107.                                                                      
   III  H        3,4-Cl.sub.2 -ph                                         
                       160-161° C.                                 
108.                                                                      
   III  H        3,5-Cl.sub.2 -ph                                         
                       101-105° C.                                 
109.                                                                      
   III  H        3-F-ph                                                   
                       172-175° C.                                 
110.                                                                      
   III  H        3-Br-ph                                                  
                       105-110° C.                                 
111.                                                                      
   III  H        2-F-ph                                                   
                       115-120° C.                                 
112.                                                                      
   III  H        Cyclohexyl                                               
                       118-122° C.                                 
113.                                                                      
   III  H        Benzyl                                                   
                       119-124° C.                                 
114.                                                                      
   III  H        n-Hexyl                                                  
                       Oil    7.45(1H, s, olefinic H),                    
                              4.74(2H, s, CH.sub.2),                      
                              3.64(2H, t, CH.sub.2),                      
                              1.72(2H, m, CH.sub.2),                      
                              1.35(6H, m, 3CH.sub.2).                     
                              0.90(3H, t, CH.sub.3)                       
115.                                                                      
   III  H        2,6-Cl.sub.2 -ph                                         
                       115-120° C.                                 
116.                                                                      
   III  H        3,5-Me.sub.2 -ph                                         
                       80-85° C.                                   
117.                                                                      
   III  H        2,4-Me.sub.2 -ph                                         
                       119-124° C.                                 
118.                                                                      
   III  H        4-Et-ph                                                  
                       129-132° C.                                 
119.                                                                      
   III  H        3-Et-ph                                                  
                       82-87° C.                                   
120.                                                                      
   III  H        n-Octyl                                                  
                       Oil    7.44(1H, s, olefinic H),                    
                              4.72(2H, s, CH.sub.2),                      
                              3.62(2H, t, CH.sub.2),                      
                              1.72(2H, m, CH.sub.2),                      
                              1.30(10H, m, 5CH.sub.2),                    
                              0.90(3H, t, CH.sub.3)                       
121.                                                                      
   III  H        n-Dodecyl                                                
                       50-52° C.                                   
__________________________________________________________________________
 
    
     EXAMPLE 1 
     Preparation of 2-(4-Chlorophenyl)-4-3-Iodopropargyl) -1,3,4-Oxadiazolin-5-one (Compound #1) 
     To the suspension of 4-chlorobenzhydrazide (8.53 g, 0.05 mole) in methylene chloride (100 ml), equipped with a magnetic stirring bar, a nitrogen inlet, a dropping funnel, and an outlet connected to diluted base solution for trapping the HCl gas, was dropwise added trichloromethyl chloroformate (5.94 g, 0.03 mole). After addition, the reaction mixture was heated to reflux for 2 hr. The reaction was cooled down to room temperature and poured into a mixture of water (500 ml) and hexane (200 ml) and stirred for 10 to 20 min. The resultant precipitate was collected by suction-filtration and was washed with hexane to give a solid product. The product was dried in air at room temperature overnight yielding 5.5 g (60% yield) of 2-(4-chlorophenyl)-1,3,4-oxadiazolin-5-one as a solid, m.p.=225°-227° C. NMR and IR spectra showed the desired structure. Without further purification, this product was subjected to the next step. 
     To the suspension of 2-(4-chlorophenyl)-1,3,4-oxadiazolin-5-one (2 g, 0.01 mole) in acetone (50 ml) was added potassium carbonate (2 g, 0.015 mole), followed by propargyl bromide (1.6 g of 80% in toluene, 0.0106 mole) with magnetic stirring under nitrogen for 3 hr. The reaction mixture was cooled down to room temperature. The suspension was filtered by suction-filtration and the solid was washed with acetone. The filtrate was concentrated to about 10 ml and was poured into water (200 ml). The resultant precipitate was collected by suction-filtration and washed with water and hexane affording 0.85 g (36% yield), after drying in air, of 2-(4-chlorophenyl)-4-propargyl-1,3,4-oxadiazolin-5-one as a solid. m.p.=125°-127° C. NMR and IR spectra showed the desired structure. Without further purification, this compound was subjected to the next step. 
     To the suspension of 2-(4-chlorophenyl)-4-propargyl-1,3,4-oxadiazolin-5-one (0.6 g, 0.00256 mole) in acetone (20 ml) with magnetic stirring at room temperature was added N-iodosuccinimide (0.6 g, 0.00266 mole), followed by silver nitrate (0.040 g, 0.00024 mole). The reaction mixture was stirred at room temperature for one hour. The suspension was filtered gravitationally and the solid was rinsed with acetone. The filtrate was poured into water (300 ml). The resultant precipitate was collected by suction-filtration and air-dried to give 0.8 g (92% yield), of 2-(4-chlorophenyl)-4-(3-iodopropargyl)-1,3,4-oxadiazolin-5-one as a solid. m.p.=151°-152° C. The proton NKM spectrum was consistent with the desired structure. 
     EXAMPLE 2 
     1-(3-Iodopropargyl)-3-(4-chlorophenyl)-4-ethyl-1,2,4-triazolin-5-one (Compound #20) 
     To a suspension of 4-chlorobenzhydrazide (98.5 g, 0.05 mole) in tetrahydrofuran (100 ml) at room temperature ethylisocyanate (4.2 g, 0.05 mole) was added slowly with magnetic stirring. The reaction was slightly exothermic and the reaction mixture turned to a thick paste. Stirring was continued an additional 30 min after which the solid was collected by suction-filtration and washed with a small amount of tetrahydrofuran and dried to provide 11.6 g (96.6% yield), of 1-(4chlorobenzoyl)-4-ethyl semicarbazide as a white solid., m.p.=242°-243° C. The above semicarbazide (10 g, 0.0414 mole) was dissolved in 1N sodium hydroxide solution (100 ml) and was refluxed with stirring for 16 hr. The solution was cooled down to about 10° C. by an ice bath and was neutralized by conc. hydrogen chloride until pH 2. The resultant white solid was collected by suction-filtration and washed with water to give 8.65 g (93.5% yield) of 3-(4-chlorophenyl)-4-ethyl-1,2,4-triazolin-5-one as a white solid. m.p.=190°-197° C. A proton NMR spectrum was consistent with the desired structure. 
     To the solution of 3-(4-chlorophenyl)-4-ethyl-1,2,4-triazolin-5-one (2.23 g, 0.01 mole) in dry acetone (40 ml) was added, at room temperature, potassium carbonate (1.67 g, 0.012 mole) followed by propargyl bromide (1.8 g of 80% in toluene, 0.012 mole). The reaction mixture was then refluxed with stirring for 6 hr. The mixture was cooled down to room temperature and solvent was evaporated to give a residue. The product was purified by crystallization from hexane/ether, affording 1.8 g (69.2% yield) of 1-propargyl-3-(4-chlorophenyl)-4-ethyl-1,2,4-triazolin-5-one as a white solid. m.p.=115°-119° C. A proton NMR spectrum was consistent with the desired structure. 
     To the solution of 1-propargyl-3-(4-chlorophenyl)-4-ethyl-1,2,4-triazolin-5-one (1.0 g , 3.82 mmole) in dry acetone (20 ml) was added N-iodosuccinimide (0.95 g, 4.2 mmole), followed by silver nitrate (50 mg, 0.29 mmole) with magnetic stirring at room temperature. The reaction mixture was stirred for 1 hr. The resultant suspension was filtered and the filtrate was poured into water (250 ml). A yellowish white solid slowly precipitated out and was collected by suction-filtration and washed with water to give 1.12 g (76% yield) of 1-(3-iodopropargyl)-3-(4-chloro-phenyl)-4-ethyl-1,2,4-triazolin-5-one as a light yellow solid. m.p.=115°-120° C. A proton NMR spectrum was consistent with the desired compound. 
     EXAMPLE 3 
     Preparation of 2-phenyl-4-iodopropargyl-1,3,4-thiadiazolin-5-one (Compound 59) 
     A. Preparation of Thiobenzhydrazide 
     A cold solution of S-(thiobenzoly)thioglycolic acid (12.25 g, 57.6 mmole) in 1N NAOH (60 ml, 60 mmole NAOH) was slowly added to a solution of hydrazine monohydrate (6 g, 123.8 mmole) in 5 ml of water at about 5° C. with magnetic stirring. After the addition, the resultant yellow suspension was stirred at room temperature for one hour. The mixture was cooled down to 5° C. and was acidified with conc. HCl until pH=6. The yellow solid was collected by suction-filtration and was washed with water to afford 3.70 g, after drying in air. m.p.=66°-68° C. 
     B. Preparation of 2-phenyl-1,3,4-thiadiazolin-5-one 
     To a solution of thiobenzhydrazide (3.7 g, 24.34 mmole) in methylene chloride (50 ml), equipped with magnetic stirrer, nitrogen inlet, and an outlet connected to a trap containing a diluted NAOH solution, was added trichloromethyl chloroformate (4 g, 20.2 mmole). The reaction mixture was stirred at room temperature for one hour. The mixture was diluted with methylene chloride (100 ml) and washed with water (3×50 ml) and brine. The organic layer was dried over MgSO 4 . After the drying agent was filtered off the filtrate was concentrated to a residue. The residue was triturated with hexane and the solid product was collected by suction-filtration to give 3.7 g as a powder. m.p.=140°-143° C. 
     C. Preparation of 2-phenyl-4-propargyl-1,3,4-thiadiazolin-5-one 
     To the solution of 2-phenyl-1,3,4-thiadiazolin-5-one (3 g, 16.85 mmole) in dry acetone (30 ml) under nitrogen with magnetic stirring was added potassium carbonate (3 g, 22 mmole), followed by propargyl bromide (3 g, 80% in toluene, 20 mmole) at room temperature. The mixture was refluxed for one hour. The reaction mixture was cooled down to room temperature and the solid was filtered off by suction-filtration. The filtrate was diluted with ether (200 ml) and washed with water (2×50 ml) and brine. The organic layer was dried over sodium sulfate. After the drying agent was filtered off the filtrate was concentrated to about 5 ml. Hexane was added to precipitate out the product. The product was collected by suction-filtration and washed with a little hexane to afford 2 g of 2-phenyl-4-propargyl-1,3,4-thiadiazolin-5-one as a powder. m.p.=73°-75° C. 
     D. Preparation of 2-phenyl4-iodopropargyl-1,3,4-thiadiazolin-5-one 
     To the solution of 2-phenyl-4-propargyl-1,3,4-thiadiazolin-5-one (1.6 g, 7.4 mmole) in dry acetone (25 ml) under nitrogen with magnetic stirring was added catalytic amount of silver nitrate 0.1 g, 0.58 mmole), followed by N-iodosuccinimide (1.85 g, 8.15 mmole). The reaction mixture was stirred at room temperature for 20 hours. The solid was filtered off by suction-filtration through a Celite filter. The filtrate was diluted with water (200 ml) and extracted with ethyl acetate (2×100 ml). The organic layer was washed with water (2×50 ml), brine, and dried over sodium sulfate. The drying agent was filtered off and the filtrate was concentrated to give a residue. The residue was triturated with hexane and the product was collected by suction-filtration to give 1.75 g as a semicrystalline compound. m.p.=117°-119° C. Proton NMR spectrum showed the desired compound. 
     EXAMPLE 4 
     Biocidal Evaluations of Compounds 
     A minimum inhibitory concentration (MIC) value is obtained using a broth, two-fold serial dilution test performed as follows: A stock solution or dispersion of the test compound, typically at a concentration of 1%, is made in a 5:3:2 solvent solution of acetone, methanol, and water. A volume of the stock solution is dispensed into culture media to give an initial starting test concentration of 500 PPM. 250 ppm, or 12 5 ppm compound. 
     When the test is ready to be done, each vessel in the dilution series, except the first vessel, contains an equal volume of compound free broth. The first vessel contains twice the volume of broth with the starting concentration of test compound. One half of the broth from the first vessel is transferred to the second vessel. After being mixed, one half the resulting volume is removed from the second vessel and transferred to the third vessel. The entire cycle is repeated sufficiently to give a series of concentrations amounting to 500, 250, 125, 63, 31, 16, 8, and 4 ppm or 250, 125, 63, 32, 16, 8, 4, 2, 1, 0.5, 0.25, and 0. 12 (or 100, 50, 25, 12.5, 6.2, 3.1, 1.6, and 0.8), respectively. 
     Each vessel is then inoculated with a cell suspension of the appropriate test organism. Bacteria are grown in broth and fungi on agar slants and algae is grown in cooling tower media for a time and at a temperature appropriate to the species being tested. At the end of the growth period, the broth is vortexed to disperse the cells. In the case of fungi, the spores are harvested by pipetting water onto the slant and dislodging the spores with a sterile loop. The cell/spore suspension is standardized by controlling incubation time, temperature, and the volume of the diluent. The suspension is then used to inoculate the vessels containing the broth compound. The vessels are then incubated at the appropriate temperature. After the incubation, the vessels are examined for growth/no growth. The minimum inhibitory concentration (NEC) is defined as the lowest concentration of compound that results in complete inhibition of growth of the test organism. 
     The organisms tested to demonstrate biocidal activity include: 
     BACTERIA: 
     Pseudomonas fluorescens (Ps.fl), gram negative 
     Pseudomonas aerugenosa (Ps.ae), gram negative 
     Escherichia coli (E.c), gram negative 
     Staphylococcus aureus (S.a), gram positive 
     FUNGI: 
     Aspergillus niger (A.n) 
     Aureobasidium pullulans (A.p) 
     ALGAE: 
     Chlorella pyroidenosa (see Table 5) 
     
                       TABLE 2                                                     
______________________________________                                    
Biocidal Evaluation                                                       
The Result of Minimum Inhibitory Concentration (MIC) Tests                
       MIC (ppm)                                                          
Compound #                                                                
         Psfl    Psae    Ecol  Saur  Anig  Apul                           
______________________________________                                    
 1.      &gt;100    &gt;100    &gt;100  &gt;100  &lt;0.8  &lt;0.8                           
 2.      &gt;100    &gt;100    &gt;100  &gt;100  &lt;0.8  &lt;0.8                           
 3.      100     &gt;100    &gt;100  &gt;100  &gt;100  &lt;0.8                           
 4.      100     &gt;100    &gt;100  &gt;100  2     &lt;0.8                           
 5.      &gt;100    &gt;100    &gt;100  50    &lt;0.8  &lt;0.8                           
 6.      &gt;100    &gt;100    &gt;100  13    &lt;0.8  &lt;0.8                           
 7.      50      50      25    13    &lt;0.8  &lt;0.8                           
 8.      50      100     25    25    &lt;0.8  &lt;0.8                           
 9.      &gt;100    &gt;100    &gt;100  &gt;100  &lt;0.8  &lt;0.8                           
10.      13      13      13    6     &lt;0.8  &lt;0.8                           
11.      50      100     &gt;100  50    &lt;0.8  &lt;0.8                           
12.      &gt;100    &gt;100    &gt;100  &gt;100  &lt;0.8  &lt;0.8                           
13.      &gt;500    &gt;500    &gt;500  &gt;500  250   8                              
14.      &gt;500    &gt;500    &gt;500  &gt;500  500   32                             
15.      &gt;500    125     &gt;500  &gt;500  63    &lt;4                             
16.      &gt;500    125     125   &gt;500  125   &lt;4                             
17.      &gt;500    &gt;500    &gt;500  &gt;500  8     &lt;4                             
18.      &gt;500    &gt;500    &gt;500  &gt;500  &lt;4    &lt;4                             
19.      100     25      50    25    &lt;0.8  &lt;0.8                           
20.      100     25      50    13    &lt;0.8  &lt;0.8                           
21.      &gt;100    100     50    25    &lt;0.8  1.6                            
22.      &gt;100    &gt;100    &gt;100  50    6.3   3                              
23.      &gt;100    &gt;100    &gt;100  50    13    3                              
24.      &gt;100    &gt;100    &gt;100  100   6     3                              
25.      &gt;100    &gt;100    50    25    &lt;0.8  &lt;0.8                           
26.      &gt;100    &gt;100    50    1.6   &lt;0.8  1.6                            
27.      50      100     &gt;100  100   100   2                              
28.      &gt;100    &gt;100    &gt;100  50    25    &lt;0.8                           
29.      100     &gt;100    &gt;100  25    6.3   &lt;0.8                           
30.      &gt;100    &gt;100    50    13    &lt;0.8  &lt;0.8                           
31.      &gt;100    50      50    25    1.6   &lt;0.8                           
32.      100     50      50    25    &lt;0.8  &lt;0.8                           
33.      &gt;100    50      25    25    13    25                             
34.      &gt;100    &gt;100    &gt;100  50    13    13                             
35.      &gt;100    &gt;100    &gt;100  50    25    6                              
36.      100     &gt;100    &gt;100  &gt;100  &lt;0.8  3                              
37.      100     100     &gt;100  100   &lt;0.8  3                              
38.      &gt;100    100     &gt;100  &gt;100  2     6.3                            
39.      &gt;100    &gt;100    &gt;100  &gt;100  2     6.3                            
40.      &gt;100    &gt;100    &gt;100  &gt;100  50    25                             
41.      &gt;100    &gt;100    &gt;100  &gt;100  6.3   6.3                            
42.      &gt;100    &gt;100    &gt;100  50    13    6                              
43.      100     50      &gt;100  &gt;100  6     &lt;0.8                           
44.      &gt;100    &gt;100    &gt;100  25    13    6                              
45.      &gt;100    &gt;100    &gt;100  &gt;100  &gt;100  &gt;100                           
46.      &gt;100    &gt;100    &gt;100  &gt;100  &gt;100  &gt;100                           
47.      63      63      63    125   16    8                              
48.      16      250     250   32    16    &lt;4                             
49.      32      32      63    125   8     &lt;4                             
50.      &gt;500    &gt;500    &gt;500  &gt;500  63    &lt;4                             
51.      63      250     63    63    32    &lt;4                             
52.      63      250     32    125   32    &lt;4                             
53.      16      63      32    32    &lt;4    &lt;4                             
54.      16      125     32    32    8     &lt;4                             
55.      16      125     32    32    8     &lt;4                             
56.      16      125     16    32    &lt;4    &lt;4                             
57.      32      125     32    63    8     &lt;4                             
58.      16      125     63    125   32    16                             
59       250     &gt;250    &gt;250  250   &lt;4    4                              
61       250     125     32    32    &lt;4    &lt;4                             
62       250     250     250   250   &lt;4    &lt;4                             
63       250     250     250   500   &lt;4    &lt;4                             
64       250     250     250   500   &lt;4    &lt;4                             
65       250     250     250   500   &lt;4    &lt;4                             
66       8       63      32    250   &lt;4    &lt;4                             
67       8       32      16    &lt;4    &lt;4    &lt;4                             
68       63      125     &gt;500  125   &lt;4    16                             
69       &gt;250    &gt;250    &gt;250  &gt;250  4     &gt;250                           
70       63      63      &gt;500  125   &lt;4    --                             
71       125     63      &gt;500  250   8     --                             
72       &gt;500    &gt;500    &gt;500  &gt;500  &gt;500  &gt;500                           
73       &gt;250    &gt;250    &gt;250  &gt;250  &gt;250  &gt;250                           
74       &gt;250    &gt;250    &gt;250  &gt;250  250   &gt;250                           
75       &gt;250    &gt;250    &gt;250  &gt;250  &gt;250  8                              
76       &gt;250    &gt;250    &gt;250  &gt;250  2     8                              
77       --      63      &gt;250  8     &lt;0.12 16                             
78                                                                        
79                                                                        
80       32      250     250   32    4     --                             
81       32      250     250   63    16    --                             
82       32      125     250   32    2     --                             
83       125     250     &gt;250  250   32    --                             
84       63      250     250   63    16    8                              
85       125     &gt;250    &gt;250  63    16    8                              
86       &gt;250    &gt;250    &gt;250  &gt;250  32    32                             
87       --      &gt;250    &gt;250  &gt;250  8     --                             
88       --      &gt;250    &gt;250  &gt;250  63    --                             
89       --      &gt;250    &gt;250  250   16    8                              
90       --      &gt;250    &gt;250  250   32    16                             
91       --      &gt;250    &gt;250  &gt;250  &gt;250  &gt;250                           
92       --      250     &gt;250  125   4     4                              
93       --      125     &gt;250  63    8     8                              
94       --      &gt;250    &gt;250  250   16    8                              
95       32      250     &gt;250  63    &lt;0.12 --                             
96       125     &gt;250    &gt;250  &gt;250  &lt;0.12 --                             
97       63      &gt;250    &gt;250  125   4     4                              
98       63      &gt;250    &gt;250  125   4     4                              
99       &gt;250    &gt;250    &gt;250  &gt;250  8     4                              
100      63      125     125   125   1     2                              
101      63      250     &gt;250  63    16    8                              
102      63      &gt;250    250   63    0.25  2                              
103      125     &gt;250    &gt;250  63    1     4                              
104      63      125     125   63    &lt;0.12 &lt;0.12                          
105      125     250     &gt;250  &gt;250  &lt;0.12 &lt;0.12                          
106      125     &gt;250    &gt;250  &gt;250  &gt;250  &gt;250                           
107      --      125     &gt;250  250   2     16                             
108      250     &gt;250    &gt;250  250   2     4                              
109      &gt;250    &gt;250    &gt;250  &gt;250  32    16                             
110      --      &gt;250    &gt;250  125   2     1                              
111      --      &gt;250    &gt;250  &gt;250  2     1                              
112      --      &gt;250    &gt;250  &gt;250  2     2                              
113      --      &gt;250    &gt;250  &gt;250  0.25  0.25                           
114      --      &gt;250    &gt;250  &gt;250  --    --                             
115      --      250     &gt;250  250   32    16                             
116      --      &gt;250    &gt;250  250   16    8                              
117      --      &gt;250    &gt;250  &gt;250  32    8                              
118      --      63      250   250   16    8                              
119      --      125     &gt;250  250   32    8                              
120      --      63      &gt;250  4     &lt;0.12 &lt;0.12                          
121      --      &gt;250    &gt;250  &gt;250  &gt;250  &gt;250                           
______________________________________                                    
 
    
     EXAMPLE 5 
     In-Vitro Plant Fungicide Tests of Compounds 
     The organisms employed in the test are: 
     PYU Pythium ultimum (Oomycete) 
     PHY Phytophthora capsici (Oomycete) 
     PIR Piricularia oryzae (Ascomycete) 
     FM Cochliobolus sativus (Ascomycete) 
     BOC Botrytis cinerea (Ascomycete) 
     FUS Fusarium roseum (Ascomycete) 
     SEP Septoria nodorum (Ascomycete) 
     RHI Rhizoctonia solani (Basidiomycete) 
     XAN Xanthomonas campestris (bacterium) 
     Methods 
     1. Culture maintenance: Transfers in steps 1 and 2 are done in a laminar flow hood. All 8 fungi and the bacterium used in this test are transferred and maintained on potato dextrose agar plates each week (2 plates/organism). Organisms are used when they are the following ages: a. 1 week old: PYU, PHY, RHI; b. 2 weeks old: XAN, PIR, BOC, HEL, FUS, SEP, COL, MON, CER, UST, ALT; c. 3 weeks old: PSH, VEN. Pythium ultimum and Phytophthora capsici are transferred to asparagine-sucrose broth shake cultures (ASB). Rhizoctonia solani, Fusarium roseum, and Zanthomonas campestris are mainted in yeast extract-dextrose broth (YDB) on a shaker. Culture flasks are inoculated with 6 mycelial plugs each (except for Pythium which is inoculated with only 3 plugs) taken from PDA plates. All liquid shaker cultures are used after 2 days growth. 
     2. Inoculum preparation. Conidia and mycelium from PIR, BOC, HEL, SEP, COL, MON, CER, PSH, UST and ALT are lightly scraped off into YDB so that mostly conidia are used as inoculum. The conidial suspension is strained through a double layer of cheesecloth to remove mycelial clumps. One plate produces enough conidia or mycelium to inoculate 100 n-d of YDB. XAN broth culture is poured (1 ml culture/100 ml broth) into YDB. PYU, PHY, RFU and FUS cultures are ground up (2-3 5 second bursts in a blender) and an but Pythium and Phytophthora are filtered through a double layer of sterile cheesecloth to remove large mycelial clumps. Ten ml of the culture solutions of R. solani and F. roseum are added to 90 ml of YSB and 10 ml of the P. capsici is added to 90 ml ASB. Two ml of the culture solution of P. ultimum is added to 98 ml of ASB. Care must be made not to overinoculate (e.g. solutions should appear fairly dear to the eye, yet when held up to light a faint cloudiness should be visible) or standards will not behave properly. The inoculum mixtures are placed in microtiter plates using a 12-tipped pipet. 175 μl (single dose) or 100 μl (dose-response test) of inoculum broth is placed in each well of the microtiter plates. The plates with inoculated media are placed in the refrigerator overnight. There are two replications per treatment. 
     3. Addition of compounds. This operation is carried out in a chemistry hood. Six microtiter plates have 245 microtiters of sterile water added to their wells ahead of time. 10 mg a.i. of the compounds are placed in 1 ml 1:1 acetone:methanol. 5 microliters of this solution is pipetted into the microtiter plates containing the sterile water according to the grid. There are 45 compounds and 3 scattered control treatments per plate. There are 2 replicates per treatment. 25 microtiters of solution is transferred to the inoculated plates with a 96 well replicator. The replicator is flame sterilized with alcohol, rinsed with sterile water, and blotted on sterile paper towells between each transfer. 
     
                                           TABLE 3                                 
__________________________________________________________________________
The Results of In-Vitro Plant Fungicide Tests                             
Dose      % Control                                                       
Compound                                                                  
      (PPM)                                                               
          PYU XAN PIR PHY                                                 
                         BOC HEL                                          
                                RHI FUS                                   
                                       SEP                                
__________________________________________________________________________
  1.  25  100 0   100 100                                                 
                         100 100                                          
                                100 100                                   
                                       100                                
  2.  25   95 0    75  95                                                 
                          0   75                                          
                                100 100                                   
                                        95                                
  3.  25  100 0    75  75                                                 
                          0   90                                          
                                 95 100                                   
                                        95                                
  4.  25  100 0    95  95                                                 
                          0  100                                          
                                 90 100                                   
                                       100                                
  5.  25  100 0   100 100                                                 
                          50  95                                          
                                100 100                                   
                                       100                                
  6.  25  100 0   100 100                                                 
                         100 100                                          
                                100 100                                   
                                       100                                
  7.  25  100 0   100 100                                                 
                         100 100                                          
                                100 100                                   
                                       100                                
  8.  25  100 0   100 100                                                 
                         100 100                                          
                                100 100                                   
                                       100                                
  9.  25   0  0    0   0  0   75                                          
                                 90 100                                   
                                        0                                 
 10.  25   50 0    0  100                                                 
                          0   90                                          
                                 0  100                                   
                                       100                                
 11.  25  100 0   100  95                                                 
                          90  95                                          
                                100 100                                   
                                       100                                
 12.  25   95 0    95  90                                                 
                          50 100                                          
                                 90 100                                   
                                       100                                
 13.  25  100 0   100 100                                                 
                          0  100                                          
                                100 100                                   
                                       100                                
 14.  25  100 0   100 100                                                 
                          0  100                                          
                                100 100                                   
                                       100                                
 15.  25  100 0   100 100                                                 
                          0  100                                          
                                100 100                                   
                                       100                                
 16.  25  100 0   100 100                                                 
                          0  100                                          
                                100 100                                   
                                       100                                
 17.  25   95 0   100 100                                                 
                          0  100                                          
                                 95 100                                   
                                       100                                
 18.  25  --  0   100 100                                                 
                          75 100                                          
                                100 100                                   
                                       100                                
 19.  25  100 0   100 100                                                 
                          0   95                                          
                                100 100                                   
                                       100                                
 20.  25  100 0   100 100                                                 
                          0   95                                          
                                100 100                                   
                                       100                                
 21.  25  100 0   100 100                                                 
                          0  100                                          
                                100 100                                   
                                       100                                
 22.  25  100 0   100 100                                                 
                          0  100                                          
                                100 100                                   
                                       100                                
 23.  25  100 0   100 100                                                 
                          0  100                                          
                                100 100                                   
                                       100                                
 24.  25  100 0   100 100                                                 
                           95                                             
                             100                                          
                                100 100                                   
                                       100                                
 25.  25  100 0   100 100                                                 
                          0  100                                          
                                 75 100                                   
                                       100                                
 26.  25  100 0   100 100                                                 
                          75 100                                          
                                100 100                                   
                                       100                                
 27.  25  100 0    95 100                                                 
                          0   75                                          
                                 95  90                                   
                                        50                                
 28.  25   95 0   100 100                                                 
                          0   95                                          
                                100  95                                   
                                       100                                
 29.  25  100 0   100 100                                                 
                          0  100                                          
                                100  95                                   
                                        75                                
 30.  25  100 0   100 100                                                 
                          0  100                                          
                                100 100                                   
                                       100                                
 31.  25  100 0   100 100                                                 
                          0  100                                          
                                100 100                                   
                                       100                                
 32.  25  100 0   100 100                                                 
                          0  100                                          
                                100 100                                   
                                       100                                
 33.  25  100 0   100 100                                                 
                          0  100                                          
                                100 100                                   
                                       100                                
 34.  25   50 0   100  50                                                 
                          0   0  50  0  75                                
 35.  25   0  0    0   0  0   0  0   0  0                                 
 36.  25   50 0   100 100                                                 
                          0  100                                          
                                100  90                                   
                                       100                                
 37.  25  --  --  --  -- --  -- --  -- --                                 
 38.  25   90 0   100  95                                                 
                          0  100                                          
                                100 100                                   
                                       --                                 
39    25  100 0   100 100                                                 
                          0  100                                          
                                100 100                                   
                                       100                                
40    25   50 0   100  50                                                 
                          0   0  0   50                                   
                                        75                                
41    25   0  0    0   0  0   0  0   0                                    
42    25   50 0   100 100                                                 
                          0  100                                          
                                100  90                                   
                                       100                                
43    25   90 0   100  95                                                 
                          0  100                                          
                                100 100                                   
                                       --                                 
44    25   90 0   100  95                                                 
                          0  100                                          
                                100 100                                   
                                       --                                 
45    25   0  0    90  0  0   0  0   50                                   
                                        0                                 
46    25   0  0   100  0  0   50                                          
                                 50 100                                   
                                        0                                 
47    25  100 0   100 100                                                 
                         100 100                                          
                                100 100                                   
                                       100                                
48    25  100 0   100 100                                                 
                         100 100                                          
                                100 100                                   
                                       100                                
49    25  100 0   100 100                                                 
                         100 100                                          
                                100 100                                   
                                       100                                
50    25  100 0    95 100                                                 
                         100  95                                          
                                 95  95                                   
                                        95                                
51    25  100 0   100 100                                                 
                         100 100                                          
                                100 100                                   
                                       100                                
52    25  100 0   100 100                                                 
                         100 100                                          
                                100 100                                   
                                       100                                
53    25  100 0   100 100                                                 
                         100 100                                          
                                100 100                                   
                                       100                                
54    25  100 0   100 100                                                 
                         100 100                                          
                                100 100                                   
                                       100                                
55    25  100 0   100 100                                                 
                         100 100                                          
                                100 100                                   
                                       100                                
56    25  100 0   100 100                                                 
                         100 100                                          
                                100 100                                   
                                       100                                
57    25  100 0   100 100                                                 
                         100 100                                          
                                100 100                                   
                                       100                                
58    25  100 0   100 100                                                 
                          90 100                                          
                                100 100                                   
                                       100                                
59    25  100 0   100 100                                                 
                         100 100                                          
                                100 100                                   
                                       100                                
60    25   0  0   100  0  0   50                                          
                                 0   0  0                                 
61    25  100 0   100 100                                                 
                         100 100                                          
                                100 100                                   
                                       100                                
62    25   0  0    0   0  0   0  0   0  0                                 
63    25  100 0   100 100                                                 
                         100 100                                          
                                100 100                                   
                                       100                                
64    25  100 0   100 100                                                 
                         100 100                                          
                                100 100                                   
                                       100                                
65    25  100 0   100 100                                                 
                         100 100                                          
                                100 100                                   
                                       100                                
66    25  100 0    95 100                                                 
                         100 100                                          
                                100 100                                   
                                       10                                 
67    25  100 0   100 100                                                 
                         100 100                                          
                                100 100                                   
                                       100                                
68    25  100 0   100 100                                                 
                          90 100                                          
                                100 100                                   
                                       100                                
69    25  100 0   100  95                                                 
                          50  95                                          
                                 50  0  95                                
70    25  100 0   100 100                                                 
                          75 100                                          
                                100 100                                   
                                       100                                
71    25  100 0   100 100                                                 
                          90 100                                          
                                100 100                                   
                                       100                                
72    25  100 0   100 100                                                 
                          0   50                                          
                                 75  0  95                                
73    25   0  0    0   50                                                 
                          0   50                                          
                                 0   0  0                                 
74    25  100 0   100 100                                                 
                          0   75                                          
                                100  0  0                                 
75    25   90 0    75  90                                                 
                          0   0 100  0  0                                 
76    12   0  0   100 100                                                 
                          0   0  50  0  50                                
77    --  --  --  --  -- --  -- --  -- --                                 
78    25  100 0   100 100                                                 
                          0   75                                          
                                100 100                                   
                                       100                                
79    25  100 0   100 100                                                 
                          75 100                                          
                                100 100                                   
                                        50                                
80    25  100 0   100 100                                                 
                          50 100                                          
                                100 100                                   
                                        50                                
81    25  100 0   100 100                                                 
                          0  100                                          
                                100  0  0                                 
82    25  100 0   100 100                                                 
                         100 100                                          
                                100 100                                   
                                       100                                
83    25  100 0   100 100                                                 
                          0   75                                          
                                100 100                                   
                                        50                                
84    25  100 0   100 100                                                 
                          50 100                                          
                                100 100                                   
                                       100                                
85    25  100 0   100 100                                                 
                          50 100                                          
                                100 100                                   
                                       100                                
86    25  100 0   100 100                                                 
                         100  75                                          
                                100 100                                   
                                       100                                
87    --  --  --  --  -- --  -- --  -- --                                 
88    --  --  --  --  -- --  -- --  -- --                                 
95    25  100 0   100 100                                                 
                         100 100                                          
                                100 100                                   
                                       100                                
96    25  100 0   100 100                                                 
                         100 100                                          
                                100 100                                   
                                       100                                
97    --  --  --  --  -- --  -- --  -- --                                 
98    25  --  --  --  100                                                 
                         --  -- 100 100                                   
                                       --                                 
99    25  --  --  --  100                                                 
                         --  -- 100 100                                   
                                       --                                 
100   25  100 0   100 100                                                 
                         100 100                                          
                                100 100                                   
                                       100                                
101   25  100 0   100 100                                                 
                          90 100                                          
                                100 100                                   
                                       100                                
102   25  100 0   100 100                                                 
                         100 100                                          
                                100 100                                   
                                       100                                
103   25  100 0   100 100                                                 
                         100 100                                          
                                100 100                                   
                                       100                                
104   25  100 0   --  100                                                 
                          95  0  90  90                                   
                                       100                                
105   25  100 0   --  100                                                 
                         100  75                                          
                                100 100                                   
                                       100                                
106   25  100 0   100 100                                                 
                         100 100                                          
                                100 100                                   
                                       100                                
107   25  100 0   100 100                                                 
                         100 100                                          
                                100 100                                   
                                       100                                
108   25  100 0   100 100                                                 
                         100 100                                          
                                100 100                                   
                                       100                                
109   25  100 0   100 100                                                 
                         100 100                                          
                                100 100                                   
                                       100                                
110   25  100 0   100 100                                                 
                         100 100                                          
                                100 100                                   
                                       100                                
111   25  100 50  100 100                                                 
                         100 100                                          
                                100 100                                   
                                       100                                
112   25  100 0   100 100                                                 
                         100 100                                          
                                100 100                                   
                                       100                                
113   25  100 0   100 100                                                 
                         100 100                                          
                                100 100                                   
                                       100                                
114   25  100 0   100 100                                                 
                         100 100                                          
                                100 100                                   
                                       100                                
__________________________________________________________________________
 
    
     EXAMPLE 6 
     Agricultural Fungicide Evaluations of Compounds 
     The compounds of this invention were tested for fungicidal activity in vivo against cucumber downy mildew (CDM), rice blast (RB), rice sheath blight (RSB), tomato late blight (TLB), wheat powdery mildew (WPM), wheat stem rust (WSR) and wheat leaf rust (WLR) and the results are shown in Table 4. In tests on cereals (except for rice plants used for testing rice blast), the plants were trimmed about 24 hours prior to the application of the fungicide compound to provide a uniform plant height and to facilitate uniform application of the compound and inoculation with the fungus. The compounds were dissolved in a 2:1:1 mixture of water, acetone, and methanol, sprayed onto the plants, allowed to dry (four to six hours), and then the plants were inoculated with the fungus. Each test utilized control plants which were sprayed with the water, acetone, and methanol mixture and inoculated with the fungus. The remainder of the technique of each of the tests is given below and the results are reported as percent disease control (percentages of plants treated with the compounds of the present invention lacking disease signs or symptoms compared to the untreated control plants). 
     Cucumber Downy Mildew (CDM) 
     Pseudoperonospora cubensis was maintained on leaves of live Marketer cucumber plants in a constant temperature room at 65° F. to 75° F. in humid air with moderate light intensity for 7 to 8 days. A water suspension of the spores from infested leaves was obtained and the spore concentration was adjusted to about 100,000 per ml of water. 
     Marketer cucumber seedlings were inoculated by spraying the underside of the leaves with a DeVilbiss atomizer until small droplets were observed on the leaves. The inoculated plants were incubated in a mist chamber for 24 hours at about 70° F. and then subsequently incubated for 6 to 7 days in a controlled temperature room under mist at 65° F. to 75° F. Seven days after inoculation, the percent disease control was determined. 
     Rice Blast (RB) 
     Nato rice plants were inoculated with Piricularia oryzae (about 20,000 conidia per ml) by spraying the leaves and stems with an airbrush until a uniform film of inoculum was observed on the leaves. The inoculated plants were incubated in a humid environment (75° F. to 85° F.) for about 24 hours, then placed in a greenhouse environment (70° F. to 75° F.). Seven to eight days after inoculation, the percent disease control was determined. 
     Rice Sheath Blight (RSB) 
     Pellicularia filamentosa (f. sp. sasiki) was cultured on an autoclaved mixture of crushed rice seeds and potato dextrose broth (100 gms of rice seeds per 30 ml of potato dextrose broth) in a 500 ml Erlenmeyer flask. After 10 days, the culture was blended in a blender to produce a uniform inoculum. Approximately one teaspoon of inoculum was spread among Lebonnet rice seedlings on the soil surface of each pot (3 inch diameter). The inoculated seedlings were incubated for 5 days in a humidity cabinet (85° F. to 90° F.). Percent disease controls were determined immediately after removing the seedlings from the cabinet. 
     Tomato Late Blight (TLB) 
     Phytophthora infestans was cultured on four week old Pixie tomato plants in a controlled environment room (65° F. to 70° F. and 100% relative humidity). After storage, the spores were washed from the leaves with water and dispersed by DeVilbiss atomizer over three week old Pixie tomato plants which had been sprayed previously with experimental fungicides. The inoculated plants were placed in a humidity cabinet at 70° F. and constant mist for 24 hours for infection. The plants were then moved to the controlled environment room as above and scored after three more days incubation. Disease control levels were recorded as percent control four days after inoculation and five days after spraying the compounds. 
     Wheat Powdery Mildew (WPM) 
     Erysiphe graminis (f. sp. tritici) was cultured on Pennol wheat seedlings in a controlled temperature room at 65° F. to 75° F. Mildew spores were shaken from the culture plants onto Pennol wheat seedlings which had been sprayed previously with the fungicide compound. The inoculated seedlings were kept in a controlled temperature room at 65° F. to 75° F. and subirrigated. The percent disease control was rated 8 to 10 days after the inoculation. 
     Wheat Stem Rust (WSR) 
     Puccinis graminis (f. sp. Race 15B-2) was cultured on Wanzer wheat seedlings for a period of 14 days in a greenhouse. A water suspension of the spores from infested plants was obtained and the spore concentration was adjusted to about 200,000 spores per ml of deionized water. Wanzer wheat plants which had been previously treated with the fungicide compounds were inoculated by applying the stem rust spore suspension, until runoff, with a DeVilbiss atomizer at 5 lbs. per square inch air pressure. After inoculation, the plants were placed in a humid environment at approximately 75° F. where they were exposed to 12 hours of continuous darkness followed by a minimum of 3 to 4 hours of light having an intensity of about 500 footcandles. The temperature in the chamber did not exceed 85° F. At the end of the light period, the plants were placed in a greenhouse where they were permitted to grow for a period of two weeks at which time the percent disease control was determined. 
     Wheat Leaf Rust (WLR) 
     Puccinis recondita (f. sp. tritici Races PKB and PLD) was cultured on seven day old wheat (cultivar Fielder) over a 14 day period in the greenhouse. Spores were collected from the leaves with a cyclone vacuum or by settling on aluminum foil. The spores were cleaned by sieving through a 250 micron opening screen and stored or used fresh. Storage employed sealed bags in an Ultralow freezer. When stored, spores must be heat shocked for two minutes at 40° F. before use. A spore suspension is prepared from dry uredia by adding 20 mg (9.5 million) per ml of Soltrol oil. The suspension is dispensed into gelatin capsules (0.7 ml capacity) which attach to the oil atomizers. One capsule is used per flat of twenty of the two inch square pots of seven day old Fielder wheat. After waiting for at least 15 minutes for the oil to evaporate from the wheat leaves, the plants are placed in a dark mist chamber (18°-20° C. and 100% relative humidity) for 24 hours. The plants are then put in the greenhouse for the latent period and scored after 10 days for disease levels. Protective and curative tests were inoculated one day after and two days, respectively, before spraying the plants with the test chemicals. 
     
                       TABLE 4                                                     
______________________________________                                    
Green House Test Results of Plant diseases Control                        
Com-   Rate    % Control                                                  
pound  (ppm)   CDM     RB   SNW   TLB  WLR   WPM                          
______________________________________                                    
  1.   200     90       0   80     0   50     0                           
  2.   200     80      75   80     0   90    75                           
  3.   200     70       0   80     0   50    85                           
  4.   200     90      90   90     0   80    75                           
  5.   200      0      75   50    90   80    75                           
  6.   200     80      75   90     0   90    75                           
  7.   200     50      90   80    50    0     0                           
  8.   200      0      50    0     0    0     0                           
  9.   200      0       0    0     0   50     0                           
 10.   200     50      90   80     0   80    75                           
 11.   200     50       0   80     0   50    50                           
 12.   200      0       0    0     0    0     0                           
 13.   200      0       0    0     0    0     0                           
 14.   --      --      --   --    --   --    --                           
 15.   200      0       0    0     0   50     0                           
 16.   200      0       0    0     0   50     0                           
 17.   200      0      50    0     0   80     0                           
 18.   200     --      75   50     0   80     0                           
 19.   200     75       0    0    80   90     0                           
 20.   200     90      75   50    70   80    75                           
 21.   200     80       0   50    80   50     0                           
 22.   200     50      50   50     0   50     0                           
 23.   200     50      75    0    70   50    75                           
 24.   200     70       0   50    95   80    85                           
 25.   200     90      90   80    95   80     0                           
 26.   200      0       0    0    95    0    50                           
 27.   200     80       0    0    85   80     0                           
 28.   200     70      75    0    80   80     0                           
 29.   200     90       0   50    80   80    90                           
 30.   200     95       0    0    80   80    75                           
 31.   200     50      90   50    85   80    75                           
 32.   200      0       0   50    90   80     0                           
 33.   200      0       0    0    70   50    85                           
 34.   200     90      99   80    80   80    85                           
 35.   200     70      --    0     0   50     0                           
 36.   200     70      --   50    85   95     0                           
 37.   200      0      50    0     0   25    75                           
 38.   200     70       0    0     0    0     0                           
39     200      0       0   50    90   80     0                           
40     200     50       0    0    80   50    90                           
41     200      0       0    0    70   50    85                           
42     200      0      --    0    85   50     0                           
43     200     70      --   --     0   50     0                           
44     200     70      --   50    85   95     0                           
45     200      0      50    0     0   25    75                           
46     200     70       0    0     0    0     0                           
47     200      0      --   50    --   80      0                          
48     200     50      --   50    --   50    90                           
49     200      0      --   80    85   50     0                           
50     200      0      --    0     0   50     0                           
51     200      0      --    0    90   50     0                           
52     200      0      --    0     0   80     0                           
53     200      0      --    0     0   80     0                           
54     200      0      --   80     0   80    85                           
55     200     70      --   50     0   80     0                           
56     200      0      --   50     0   80    50                           
57     200     70      --   80    85   80    100                          
58     200     95      --    0    70   90    90                           
59     200     90       0   50     0   50     0                           
60     200     85      --    0     0    0     0                           
61     200      0      --   --    50    0     0                           
62     --      --      --   --    --   --    --                           
63     200     90      --   --    50   90     0                           
64     --      --      --   --    --   --    --                           
65     200     90      --   --    90   90     0                           
66     200     75      --   --     0   99     0                           
67     200     85      --   --    95   90     0                           
68     200     50      --   --    50   99     0                           
69     --      --      --   --    --   --    --                           
70     200     80      --   --     0    0     0                           
71     --      --      --   --    --   --    --                           
72     --      --      --   --    --   --    --                           
73     200     90      --   --     0   85    85                           
74     200      0      --   --    50   75     0                           
75     200      0      --   --     0   95     0                           
76     200     90      --   --     0   95     0                           
77     --      --      --   --    --   --    --                           
78     --      --      --   --    --   --    --                           
79     200     75      --   --    75   85     0                           
80     200     50      --   --    75   75     0                           
81     200      0      --   --     0   75     0                           
82     200     50      --   --     0    0     0                           
83     200     85      --   --    75   95     0                           
84     --      --      --   --    --   --    --                           
85     --      --      --   --    --   --    --                           
86     200     75      --   --    85   75     0                           
87     --      --      --   --    --   --    --                           
88     200     90      --   --     0    0     0                           
89     --      --      --   --    --   --    --                           
90     --      --      --   --    --   --    --                           
91     --      --      --   --    --   --    --                           
92     200     70      --   --    --   95     0                           
93     200     95      --   --     0   75     0                           
94     200     100     --   --     0   90     0                           
95     --      --      --   --    --   --    --                           
96     200     90      --   --     0   99     0                           
97     --      --      --   --    --   --    --                           
98     200     90      --   --    90   95     0                           
99     --      --      --   --    --   --    --                           
100    --      --      --   --    --   --    --                           
101    200      0      --   --     0    0     0                           
102    200      0      --   --     0   75     0                           
103    200      0      --   --     0   50     0                           
104    --      --      --   --    --   --    --                           
105    --      --      --   --    --   --    --                           
106    --      --      --   --    --   --    --                           
107    --      --      --   --    --   --    --                           
108    --      --      --   --    --   --    --                           
109    --      --      --   --    --   --    --                           
110    200     --      --   50    75   80     0                           
111    --      --      --   --    --   --    --                           
112    --      --      --   --    --   --    --                           
113    --      --      --   --    --   --    --                           
114    200     --      --   50    75   90     0                           
115    --      --      --   --    --   --    --                           
116    200     100     --   --    75   90     0                           
______________________________________                                    
 
    
     
                       TABLE 5                                                     
______________________________________                                    
Antialgal Test Results Against Green Alga                                 
                     MIC (ppm)                                            
Compound #           Chlorella                                            
______________________________________                                    
 85                  0.25                                                 
 87                  4                                                    
 88                  &lt;0.12                                                
 89                  &lt;0.12                                                
 90                  &lt;0.12                                                
107                  &lt;0.12                                                
108                  8                                                    
109                  8                                                    
110                  4                                                    
111                  &gt;250                                                 
112                  0.25                                                 
113                  8                                                    
114                  8                                                    
120                  125                                                  
121                  &lt;0.12                                                
______________________________________