Polymorphs of methyl 3-(e)-2--3-methoxyacrylate

Abstract

The present invention relates to novel crystalline polymorphic and amorphous forms of the compound (E)-2-{2-[6-(2-cyanophenoxy) pyrimidin-4-yloxy] phenyl}-3-methoxy-acrylate (azoxystrobin). Infrared Raman spectra, X-ray powder diffraction pattern and differential scanning calorimetry thermogram of two polymorphs “A” and “B” are provided. Further, the present invention also provides methods for preparing the novel polymorphic forms “A” and “B”, as well as processes for producing mixtures of the polymorphs, and a process for preparing amorphous azoxystrobin. Yet further, the present invention provides anti-fungal compositions comprising the novel crystalline polymorphs “A” and “B” or amorphous azoxystrobin, which are useful for controlling and combating fungi grown on agricultural and horticultural crops and up-land, and methods of using the same as pesticidal agents for combating fungi on agricultural and horticultural crops.

1 . An amorphous methyl (E)-2-{2-[6-(2-cyanophenoxy)pyrimidin-4-yloxy]phenyl}-3-methoxyacrylate. 
     
     
         2 . The amorphous compound according to  claim 1 , which exhibits an X-ray powder diffraction pattern substantially as shown in  FIG. 10 . 
     
     
         3 . A process for preparation of amorphous methyl (E)-2-{2-[6-(2-cyanophenyoxy)pyrimidin-4-yloxy]phenyl}-3-methoxyacrylate, the process comprising:
 heating methyl (E)-2-{2-[6-(2-cyanophenyoxy)pyrimidin-4-yloxy]phenyl}-3-methoxyacrylate to a temperature greater than its melting point;   fast cooling; and   isolating the amorphous methyl (E)-2-{2-[6-(2-cyanophenyoxy)pyrimidin-4-yloxy]phenyl}-3 -methoxyacrylate.   
     
     
         4 . The process according to  claim 3 , wherein the temperature is greater than about 100° C. 
     
     
         5 . The process according to  claim 3 , wherein the temperature is greater than about 120° C. 
     
     
         6 . A composition for combating fungus, comprising amorphous methyl (E)-2-{2-[6-(2-cyanophenoxy)pyrimidin-4-yloxy]phenyl}-3-methoxyacrylate according to  claim 1  and an adjuvant. 
     
     
         7 . The composition of  claim 6 , wherein a concentration of the methyl (E)-2-{2-[6-(2-cyanophenoxy)pyrimidin-4-yloxy]phenyl}-3-methoxyacrylate in the composition is in a range of about 1 to 10,000 parts per million. 
     
     
         8 . The composition of  claim 6 , wherein a concentration of the methyl (E)-2-{2-[6-(2-cyanophenoxy)pyrimidin-4-yloxy]phenyl}-3-methoxyacrylate in the composition is in a range of about 20 to 2,000 parts per million. 
     
     
         9 . The composition of  claim 6 , wherein the composition further comprises an insecticide, an acaricide, a plant growth regulator, or a combination thereof. 
     
     
         10 . A method for combating fungus in a plant, comprising applying to the plant, to a seed of the plant or to a locus of the seed or the plant a fungicidally effective amount of the composition of  claim 6 . 
     
     
         11 . A method for protecting crops from fungus, comprising applying to the crops an effective amount of the composition of  claim 6 .