Substituted 3-phenyluracils

Abstract

where X 1 -X 4 are each O or S; W is unsubstituted or substituted —CH═O, —CH═S, —CH═NH, —CH(X 3 R 6 )(X 4 R 7 ), R 6 and R 7 are each C 1 -C 6 -alkyl, C 3 -C 6 -alkenyl, C 3 -C 6 -alkynyl or C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl or together form a carbon chain; R 10 is H, OH, SH, an ether or thioether group, unsubstituted or substituted C 1 -C 6 -alkyl, C 3 -C 6 -alkenyl, C 3 -C 6 -alkynyl, C 3 -C 7 -cycloalkyl, unsubstituted or substituted amino or unsubstituted or substituted phenyl; R 1 is halogen, CN, NO 2 or CF 3 ; R 2 is H or halogen; R 3 is H, C 1 -C 6 -alkyl, C 3 -C 6 -alkenyl, C 3 -C 6 -alkynyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -cycloalkylcarbonyl, C 1 -C 6 -cyanoalkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl, CHO, C 1 -C 6 -alkanoyl, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -haloalkylcarbonyl, unsubstituted or substituted amino, unsubstituted or substituted phenyl or phenyl-C 1 -C 6 -alkyl; R 4 and R 5 are each H, CN, halogen, unsubstituted or substituted C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 7 -cycloalkyl or unsubstituted or substituted phenyl; R 5 may additionally be NO 21 CHO, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -haloalkylcarbonyl, C 1 -C 6 -alkoxycarbonyl or unsubstituted or substituted amino, or R 4 and R 5 together form an unsubstituted or substituted carbon chain, with the proviso that R 4 is not CF 3 at the same time as R 5 is H when W is —CH═CH—CO—R 10 where R 10 is C 1 -C 6 -alkoxy or C 3 -C 7 -cycloalkoxy, and the salts and enol eithers of I in which R 3 is H, are used for the desication and defoliation of plants and as insecticides and herbicidees.

We claim:  
     
         1 . Substituted 3-phenyluracils of the general formula I  
       
         
           
           
               
               
           
         
       
       where 
 X 1  and X 2  are each oxygen or sulfur;  
 W is —C(R 8 )═X 5 , —C(R 8 )(X 3 R 6 )(X 4 R 7 ), —C(Rs)═C(R 9 )—CN, —C(R 8 )═C(R 9 ) —CO—R 10 , —CH(R 8 ) —CH(R 9 ) —CO—R 10 , —C(R 8 )═C(R 9 )—CH 2 -CO-R 10 , —C(R)═C(R 9 )—C(R 11 )═C(R) —CO—R 10  or —C(R 8 )═C(R 9 )—CH 2 -CH(R 13 )—CO—R 10  where  
 X 3  and X 4  are each oxygen or sulfur;  
 X 5  is oxygen, sulfur or a radical-NR 14 ; 
 R 14  is hydrogen, hydroxyl, C 1 -C 6 -alkyl, C 3 -C 6 -alkenyl, C 3 -C 6 -alkynyl, C 3 -C 7 -cycloalkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 3 -C 6 -alkenyloxy, C 3 -C 6 -alkynyloxy, C 5 -C 7 -cycloalkoxy, C 5 -C 7 -cycloalkenyloxy, C 1 -C 6 -haloalkoxy, C 3 -C 6 -haloalkenyloxy, hydroxy-C 1 -C 6 -alkoxy, cyano-C 1 -C 6 -alkoxy, C 3 -C 7 -cycloalkyl-C 1 -C 6 -alkoxy, C 1 -C 6 -alkoxy- C 1 -C 6 -alkoxy, C 1 -C 6 -alkoxy-C 3 -C 6 -alkenyloxy, C 1 -C 6 -alkylcarbonyloxy, C 2 -C 6 -haloalkylcarbonyloxy, C 1 -C 6 -alkylcarbamoyloxy, C 1 -C 6 -haloalkylcarbamoyloxy, C 1 -C 6 -alkoxycarbonyl-C 2 -C 6 -alkoxy, C 1 -C 6 -alkylthio-C 1 -C 6 -alkoxy, di-C 1 -C 6 -alkylamino-C 1 -C 6 -alkoxy, phenyl which may carry from one to three of the following substituents: cyano, nitro, halogen, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy and C 1 -C 6 -alkoxycarbonyl, phenyl-C 3 -C 6 -alkoxy, phenyl-C 3 -C 6 -alkenyloxy or phenyl-C 3 -C 6 -alkynyloxy, where one or two methylene groups of each of the carbon chains may be replaced with —O—, —S— or —N(C 1 -C 6 -alkyl)- and each phenyl ring may carry from one to three of the following substituents: cyano, nitro, halogen, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -alkoxycarbonyl, heterocyclyl, heterocyclyl—C 1 -C 6 -alkoxy, heterocyclyl-C 3 -C 6 -alkenyloxy or heterocyclyl-C 3 -C 6 -alkynyloxy, where one or two methylene groups of each of the carbon chains may be replaced with —O—, —S— or —N(C 1 -C 6 -alkyl)- and the heterocyclyl ring may be from three-membered to seven-membered and saturated, unsaturated or aromatic and may contain from one to four hetero atoms selected from a group consisting of one or two oxygen or sulfur atoms and up to four nitrogen atoms and furthermore may carry from one to three of the following substituents: cyano, nitro, halogen, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy or C 1 -C 6 -alkoxycarbonyl, or —N(R 15 )R 16 , where  
 R 15  and R 16  are each hydrogen, C 1 -C 6 -alkyl, C 3 -C 6 -alkenyl, C 3 -C 6 -alkynyl, C 3 -C 6 -cycloalkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy- C 1 -C 6 -alkyl, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -alkoxycarbonyl-C 1 -C 6 -alkyl or C 1 -C 6 -alkoxycarbonyl-C 2 -C 6 -alkenyl, where the alkenyl chain may additionally carry from one to three of the following radicals: halogen and cyano or phenyl which may carry from one to three of the following substituents: cyano, nitro, halogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 3 -C 6 -alkenyl, C 1 -C 6 -alkoxy and C 1 -C 6 -alkoxycarbonyl, or  
 R 15  and R 16  together with the common nitrogen atom form a saturated or unsaturated 4-membered to  7 -membered heterocyclic structure, where one ring member may be replaced with —O—, —S—, —N═, —NH— or —N(C 1 -C 6 -alkyl)-;  
 
 R 6  and R 7  are each C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 3 -C 6 -alkenyl, C 3 -C 6 -alkynyl, C 1 -C 6 -alkoxy- C 1 —C 6 -alkyl, or 
 R 6  and R 7  together form a saturated or unsaturated, two-membered to four-membered carbon chain which may carry an oxo substituent, where one member of this chain may be replaced with an oxygen, sulfur or nitrogen atom which is not adjacent to X 3  and X 4 , and where the chain may carry from one to three of the following radicals: cyano, nitro, amino, halogen, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 1 -C 6 -alkoxy, C 2 -C 6 -alkenyloxy, C 2 -C 6 -alkynyloxy, C 1 -C 6 -haloalkyl, cyano-C 1 -C 6 -alkyl, hydroxy-C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl, C 3 -C 6 -alkenyloxy-C 1 -C 6 -alkyl, C 3 -C 6 -alkynyloxy-C 1 -C 6 -alkyl, C 3 -C 7 -cycloalkyl, C 3 -C 7 -cycloalkoxy, carboxyl, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -alkylcarbonyloxy-C 1 -C 6 -alkyl and phenyl which may carry from one to three of the following radicals: halogen, cyano, nitro, amino, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy and C 1 -C 6 -alkoxycarbonyl, and where the chain may furthermore be substituted by a fused-on or spiral-bonded three-membered to seven-membered ring, and one or two carbon atoms of this ring may be replaced with oxygen, sulfur and unsubstituted or C 1 -C 6 -alkyl-substituted nitrogen atoms and this ring may carry one or two of the following substituents: cyano, C,—C 6 -alkyl, C 2 -C 6 -alkenyl, C 1 -C 6 -alkoxy, C 1 -C 6 -cyanoalkyl, C 1 -C 6 -haloalkyl and C 1 -C 6 -alkoxycarbonyl;  
 
 R 8  is hydrogen, cyano, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 1 -C 6 -haloalkyl, C 3 -C 7 -cycloalkyl, C 1 -C 6 -alkoxy- C 1 -C 6 -alkyl or C 1 -C 6 -alkoxycarbonyl;  
 R 9  and R 12  are each hydrogen, cyano, halogen, C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, halo-C 1 -C 6 -alkyl, C 1 -C 6 -alkylcarbonyl or C 1 -C 6 -alkoxycarbonyl;  
 R 10  is hydrogen, O—R 17 , S—R 17 , C 1 -C 3 -alkyl which may furthermore carry one or two C 1 -C 6 -alkoxy substituents or  
 R 10  is C 3 -C 6 -alkenyl, C 3 -C 6 -alkynyl, C 1 -C 6 -haloalkyl, C 3 -C 7 -cycloalkyl, C 1 -C 6 -alkylthio-C l -C 6 -alkyl, C 1 -C 6 -alkyliminooxy, —N(R 15 )R 16  or phenyl which may carry from one to three of the following substituents: cyano, nitro, halogen, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy or C 1 -C 6 -alkoxycarbonyl, 
 R 17  is hydrogen, C 1 -C 6 -alkyl, C 3 -C 6 -alkenyl, C 3 -C 6 -alkynyl, C 3 -C 7 -cycloalkyl, C 1 -C 6 -haloalkyl, C 3 -C 6 -haloalkenyl, cyano—C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy- C 1 -C 6 -alkyl, C 1 -C 6 -alkylthio-C 1 -C 6 -alkyl or C 1 -C 6 -alkyl-oximino-C 1 -C 6 -alkyl, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -alkylcarbonyl-C 1 -C 6 -alkyl, C 1 -C 6 -alkoxycarbonyl-C 1 -C 6 -alkyl, phenyl or phenyl-C 1 -C 6 -alkyl, where each of the phenyl radicals in turn may carry from one to three of the following substituents: cyano, nitro, halogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 3 -C 6 -alkenyl, C 1 -C 6 -alkoxy and C 1 -C 6 -alkoxycarbonyl;  
 
 R 11  is hydrogen, cyano, halogen, C 1 -C 6 -alkyl, C 3 -C 6 -alkenyl, C 3 -C 6 -alkynyl, C 1 -C 6 -alkoxy- C 1 -C 6 -alkyl, C 3 -C 6 -alkylcarbonyl, C 1 -C 6 -alkoxycarbonyl, —NR 18 R 19 , where R 18  and R 19  have the same meanings as R 15  and R 16 , or phenyl which may furthermore carry from one to three of the following substituents: cyano, nitro, halogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 3 -C 6 -alkenyl, C 1 -C 6 -alkoxy and C 1 -C 6 -alkoxycarbonyl;  
 R 13  is hydrogen, cyano, C 1 -C 6 -alkyl or C 1 -C 6 -alkoxycarbonyl; or R 9  and R 10  together form a two-membered to five-membered carbon chain in which one carbon atom may be replaced with oxygen, sulfur or unsubstituted or C 1 -C 6 -alkyl-substituted nitrogen;  
 R 1  is halogen, cyano, nitro or trifluoromethyl;  
 R 2  is hydrogen or halogen;  
 R 3  is hydrogen, nitro, C 1 -C 6 -alkyl, C 3 -C 6 -alkenyl, C 3 -C 6 -alkynyl, C 3 -C 6 -cycloalkyl, C 3 -C 8 -cycloalkylcarbonyl, cyano-C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl, formyl, C 1 -C 6 -alkanoyl, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -haloalkylcarbonyl, C 1 -C 6 -alkylcarbonyl-C 1 -C 6 -alkyl, C 1 -C 6 -alkoxycarbonyl-C 1 -C 6 -alkyl; a group —N(R 20 )R 21 , where R 20  and R 21  have one of the meanings of R 15  and R 16 ; phenyl or phenyl—C 1 -C 6 -alkyl, where each phenyl ring may carry from one to three of the following radicals: cyano, nitro, halogen, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy and C 1 -C 6 -alkoxycarbonyl; R 4  is hydrogen, cyano, nitro, halogen, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 8 -cycloalkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -hydroxyalkyl, cyano-C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -alkylthio, C 1 -C 6 -alkoxy- C 1 -C 6 -alkyl, C 1 -C 6 -alkylthio-C 1 -C 6 -alkyl or phenyl which may carry from one to three of the following radicals: cyano, nitro, halogen, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy and C 1 -C 6 -alkoxycarbonyl;  
 R 5  is hydrogen, cyano, nitro, halogen, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 7 -cycloalkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -hydroxyalkyl, cyano-C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy- C 1 -C 6 -alkyl, C 1 -C 6 -alkylthio-C 1 -C 6 -alkyl, formyl, C 1 -C 6 -alkyl-carbonyl, C 1 -C 6 -haloalkylcarbonyl, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -alkoxycarbonyl-C 2 -C 6 -alkenyl, —N(R 22  )R 23 , where R 22  and R 23  have one of the meanings of R 15  and R 16 , or phenyl which may carry from one to three of the following radicals: cyano, nitro, halogen, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy and C 1 -C 6 -alkoxy-carbonyl, or  
 R 4  and R 5  together form a saturated or unsaturated 3-membered or 4-membered carbon chain which may contain from one to three of the following hetero atoms: 1 or 2 oxygen atoms, 1 or 2 sulfur atoms and from 1 to 3 nitrogen atoms, and the chain may furthermore carry from one to three of the following radicals: cyano, nitro, amino, halogen, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 1 -C 6 -alkoxy, C 1 -C 6 -alkylthio and C 1 -C 6 -alkoxycarbonyl; with the proviso that R 4  may not be trifluoromethyl at the same time as R 5  is hydrogen when W is —CH═CH—CO—R 10  where R 10  is C 1 -C 6 -alkoxy or C 3 -C 7 -cycloalkoxy, and with the proviso that R 4  and R 5  are not simultaneously hydrogen when W is CH(R 8 )—CH(R 9 )—CO—R 10  and R 9  is not halogen, and the salts and enol ethers of those compounds I in which R 3  is hydrogen.  
 
     
     
         2 . Compounds of the general formula Ia or Ib  
       
         
           
           
               
               
           
         
       
       where the variables R 1 , R 2 , R 4 , R 5 , X 1 , X 2  and W have the meanings stated in    claim 1    and R 3′  is one of the following groups: C 1 -C 6 -alkyl, C 3 -C 6 -alkenyl or C 3 -C 6 -alkynyl, with the proviso that R 4  may not be trifluoromethyl at the same time as R 5  is hydrogen when W is —CH═CH—CO—R 10  where R 10  is C 1 -C 6 -alkoxy or C 3 -C 6 -cycloalkoxy.  
     
     
         3 . A compound as claimed in    claim 1    or    2   , wherein W is —C(R 8 )═X 5 , —C(R 8 )(X 3 R 6 )(X 4 R 7 )—C(R 8 )═C(R 9 ) —CO—R 10  or —CH(R 8 ) —CH(R 9 ) —CO—R 10 .  
     
     
         4 . A compound as claimed in    claim 1    or    2   , wherein R 3  is C 1 -C 6 -alkyl.  
     
     
         5 . A compound as claimed in    claim 1    or    2   , wherein R 2  is hydrogen or fluorine.  
     
     
         6 . A compound as claimed in    claim 1    or    2   , wherein R 1  is chlorine or bromine.  
     
     
         7 . A compound as claimed in    claim 1    or    2   , wherein R 4  is C 1 -C 6 -haloalkyl.  
     
     
         8 . Enamine esters of the general formula II  
       
         
           
           
               
               
           
         
       
       where R 1 , R 2 , R 3 , R 4 , R 5 , X 1  and W have the meanings stated in    claim 1    and L 1  is C 1 -C 6 -alkyl or phenyl.  
     
     
         9 . Enamine-carboxylates of the general formula III  
       
         
           
           
               
               
           
         
       
       where the variables R 1 , R 2 , R 3 , R 4 , R 5 , X 2  and W have the meanings stated in    claim 1    and L 1  is C 1 -C 6 -alkyl or phenyl.  
     
     
         10 . Pyrimidinone derivatives of the general formula IVa or IVb  
       
         
           
           
               
               
           
         
       
       where the variables R 1 , R 2 , R 4 , R 5 , X 1 , X 2  and W have the meanings stated in    claim 1    and Hal is halogen.  
     
     
         11 . Enamine-amides of the formula VIII  
       
         
           
           
               
               
           
         
       
       where the variables R 1 , R 2 , R 3 , R 4 , R 5 , X 2  and W have the meanings stated in    claim 1   .  
     
     
         12 . A herbicide containing an inert liquid or solid carrier and a herbicidal amount of at least one substituted 3-phenyluracil of the formula I as claimed in    claim 1    or of the formula Ia or Ib as claimed in    claim 2    or a salt or an enol ether of those compounds I in which R 3  is hydrogen.  
     
     
         13 . A method for controlling undesirable plant growth, wherein a herbicidal amount of a substituted 3-phenyluracil of the formula I as claimed in    claim 1    or of the formula Ia or Ib as claimed in    claim 2    or a salt or an enol ether of those compounds I in which R 3  is hydrogen is allowed to act on plants, on their habitat or on seed.  
     
     
         14 . An agent for the desiccation and defoliation of plants, containing, in addition to conventional additives, an amount, having a defoliant or desiccant effect, of at least one substituted 3-phenyluracil of the formula I as claimed in    claim 1    or of the formula Ia or Ib as claimed in    claim 2    or a salt or an enol ether of those compounds I in which R 3  is hydrogen.  
     
     
         15 . A method for the desiccation and defoliation of plants, wherein an amount, having a defoliant and/or desiccant effect, of a substituted 3-phenyluracil I as claimed in    claim 1    or Ia or Ib as claimed in    claim 2    is allowed to act on the plants.  
     
     
         16 . A method as claimed in    claim 15   , wherein cotton is defoliated.  
     
     
         17 . A pesticide containing inert carriers and a pesticidal amount of at least one substituted 3-phenyluracil of the formula I as claimed in    claim 1    or of the formula Ia or Ib as claimed in    claim 2    or of a salt or of an enol ether of those compounds I in which R is hydrogen.  
     
     
         18 . A method for controlling pests, wherein a pesticidal amount of a substituted 3-phenyluracil of the formula I as claimed in    claim 1    or of the formula Ia or Ib as claimed in    claim 2    or of a salt of an enol ether of those compounds I in which R 3  is hydrogen is allowed to act on pests or their habitat.  
     
     
         19 . A process for the preparation of a substituted 3-phenyluracil I as claimed in    claim 1    or Ia or Ib as claimed in    claim 2   , wherein 
 a) an enamine ester of the formula II or an enaminecarboxylate of the formula III  
                     
 where L 1  is C 1 -C 6 -alkyl or phenyl, is cyclized and, if desired, the substituted 3-phenyluracil I in which R 3  is hydrogen is liberated from the resulting metal salt by means of an acid, or  
 b) a 3-phenyluracil I in which R 3  is hydrogen is alkylated or acylated or  
 c) a 3-phenyluracil I in which R 3  is halogen is reacted with a metal cyanide or  
 d) a pyrimidinone derivative of the formula IVa or IVb  
                     
 where Hal is halogen is reacted with a compound HO—R 3 , H 5 —R 3′  Me ⊕    ⊖ OR 3 ′ or Me ⊕    ⊕ SR 3′ , where Me ⊕  is one equivalent of a metal ion, or  
 e) a 3-phenyluracil I in which W is —CO—R 8  is acetalated with a compound H—X 3 R 6 , H—X 4 R 7  or H—X 3 (R 6 R 7 )X 4 —H or  
 f) a 3-phenyluracil I in which W is —C(R) (X 3 R 6 ) (X 4 R 7 ) is subjected to acetal cleavage or  
 g) a 3-phenyluracil I in which W is —C(R 8 )═O is reacted with a phosphorylide of the formulae Va to Vd 
 R 3 P═CR 9 —CO—R 10  I Va,  
 R 3 P═C(R 9 )—CH 2 —CO—R 10  l Vb,  
 R 3 P═C(R 9 )—C(R 11 )═C(R 12 )—CO—R 10  Vc,  
 R 3 P═C(R 9 )—CH 2 —CHR 13 —CO—R 10  Vd, where R is a C-organic substituent, or with a phosphonium salt of the formulae VIa to VId  
 R 3 P ⊕ —CH(R 9 )—CO—R 10  Hal ⊖  VIa,  
 R 3 P ⊕ —CH(R 9 )—CH 2 —CO—R 10  Hal ⊖  VIb,  
 R 3 P ⊕ —CH(R 9 )—CR 11 ═CR 12 —CO—R 10  Hal ⊖  VIc,  
 R 3 P ⊕ —CH(R 9 )—CH 2 —CHR 13 —CO—R 10  Hal ⊖  VId,  
 where Hal is halogen, or with a phosphonate of the formulae VIIa to VIId  
 (RO) 2 PO—CH(R 9 )—CO—R 10  VIIa,  
 (RO) 2 PO—CH(R 9 )—CH 2 —CO—R 10  VIIb,  
 (RO) 2 PO—CH(R 9 )—CR 11 ═CR 12 —CO—R 10  VIIc,  
 (RO) 2 PO—CH(R 9 )—CH 2 —CHR 13 —CO—R 10  VlId, or  
 h) a 3-phenyluracil I in which W is —C(R 8 )═O is reacted with an amine, hydroxylamine or hydrazine H 2 N—R 14  or  
 i) a 3-phenyluracil I in which W is —C(R 8 )═N—R 14  is cleaved to give a compound I in which W is —C(R 8 )═O or  
 k) a 3-phenyluracil I in which X 2  is oxygen is reacted with a sulfurization reagent or  
 l) a 3-phenyluracil I in which R 5  is hydrogen is halogenated or  
 m) a 3-phenyluracil I in which W is cyano is reduced to a compound I in which W is formyl or  
 n) an enamide VIII as claimed in    claim 11    is cyclized with a phosgenating or thiophosgenating agent or  
 o) a 3-phenyluracil I as claimed in    claim 1   , in which W is amino, is alkylated by the Meerwein method or  
 p) a 3-phenyluracil I as claimed in    claim 1   , in which W is bromine, iodine or O—SO 2 CF 3 , is coupled with an olefin under metal catalysis.