Abstract:
m-Phenylene-N,N-methyl-(m-chlorophenyl)-Dicarbamate is synthesized by reaction of resorcinol with methylisocyanate and m-chlorophenylisocyanate. Product is useful for pre-emergence herbicide in agricultural formulation.

Description:
DESCRIPTION OF THE INVENTION 
     A new chemical compound, namely, m-Phenylene-N,N-methyl-(m-chlorophenyl)-Dicarbamate is found. The product is a compound having the following structural formula: ##SPC1## 
     The described compound is prepared by reacting one part of resorcinol with one part of methylisocyanate and one part of m-chlorophenylisocyanate in an inert solvent. 
    
    
     The following example is illustrative of the preparation of the invention compound: 
     EXAMPLE I 
     Preparation of m-Phenylene-N,N-methyl-(m-chlorophenyl)-Dicarbamate: A mixture of resorcinol (11.0 g; 0.1 mole), methylisocyanate (6.0 g; 0.1 mole), m-chlorophenylisocyanate (16.0 g; 0.1 mole) and 100 ml benzene was stirred and refluxed for 24 hours. The mixture was cooled then poured into 300 ml of cold water while stirring. The resulting solid material was filtered and dried to give 26 grams of m-Phenylene-N,N-methyl-(m-chlorophenyl)-Dicarbamate, M.P. 161°C-164°C. 
     
         ______________________________________Analysis for C.sub.15 H.sub.13 N.sub.2 O.sub.4 ClTheory: C,     56.16%      Found: C,   56.50%   H,      4.06%             H,    3.90%   N,      8.74%             N,    8.54%   Cl,    11.08%             Cl,  10.95%______________________________________ 
    
     Concentration of toxicant: The test compounds are formulated by a standard procedure of solution in acetone, addition of an emulsifier, and dilution with water. The results of screening tests are tabulated in Table I. 
     
                                           TABLE 1__________________________________________________________________________Herbicidal Screening TestsInvented Rate     Mustard            Pigweed                   Crabgrass                          Foxtail                                Corn  Wheat  Cotton BeansCompound Lbs./A     Pre Post            Pre Post                   Pre Post                          Pre                             Post                                Pre                                   Post                                      Pre Post                                             Pre Post                                                    Pre                                                       Post__________________________________________________________________________&#34;     10  2RG -- 2RG -- 1RG -- 0  -- 0  -- 2RG -- 1RG -- 0  --&#34;      5  2RG -- 2RG -- 0   -- 0  -- 0  -- 1RG -- 0   -- 0  --__________________________________________________________________________ 
    
     The letter ratings in Table I are: 
      O = None 
     2RG = Moderate reduced germination 
     1RG = Slight reduced germination