Polymorphs
The present invention relates to solid forms of the insecticide of formula (I): compositions comprising the solid forms and methods of their use as insecticides.
1. A method, comprising:
dissolving a compound of formula I,
in a methylcyclohexane containing solution;
crystallizing the dissolved compound of formula I.
2. The method of claim 1 , further comprising heating the methylcyclohexane until no solid of the compound of formula I remains.
3. The method of claim 2 , wherein the heating is to about 85 to 90° C.
4. The method of claim 1 , wherein the crystallizing is at room temperature.
5. The method of claim 1 , wherein the crystalized compound of formula I has a powder X-ray diffraction pattern comprising one 2θ angle value at 9.4±0.2, one 2θ angle value at 10.3±0.2 and at least three 2θ angle values selected from the group consisting of 8.1±0.2, 11.6±0.2, 12.0±0.2, 13.9±0.2, 14.8±0.2, 16.0±0.2, 18.2±0.2, 18.8±0.2, 20.4±0.2, 20.6±0.2, 21.2±0.2, 21.7±0.2, 21.9±0.2, 22.1±0.2, 22.4±0.2, and 23.4±0.2.
6. The method of claim 1 , wherein the crystalized compound of formula I has lattice parameters: a=8.85 ű0.01 Å, b=11.43 ű0.01 Å, c=11.96 ű0.01 Å, α=65.26°±0.01°, β=77.82°±0.01°, γ=72.60°±0.01° and volume=1043 Å 3 ±1 Å 3 .
7. The method of claim 1 , wherein the crystalized compound of formula I has a powder X-ray diffraction pattern comprises at least six 2 θ angle values selected from the group consisting of 8.1±0.2, 11.6±0.2, 12.0±0.2, 13.9±0.2, 14.8±0.2, 16.0±0.2, 18.2±0.2, 18.8±0.2, 20.4±0.2, 20.6±0.2, 21.2±0.2, 21.7±0.2, 21.9±0.2, 22.1±0.2, 22.4±0.2, and 23.4±0.2.
8. The method of claim 1 , wherein the crystalized compound of formula I has a powder X-ray diffraction pattern comprises at least nine 2θ angle values selected from the group consisting of 8.1±0.2, 11.6±0,2, 12.0±0.2, 13.9±0.2, 14.8±0.2, 16.0±0.2, 18.2±0.2, 18.8±0.2, 20.4±0.2, 20.6±0.2, 21.2±0.2, 21.7±0.2, 21.9±0.2, 22.1±0.2, 22.4±0.2, and 23.4±0.2.
9. The method of claim 1 , wherein the crystalized compound of formula I has a powder X-ray diffraction pattern comprises at least twelve 2θ angle values selected from the group consisting of 8.1±0.2, 11.6±0.2, 12.0±0.2, 13.9±0.2, 14.8±0.2, 16.0±0.2, 18.2±0.2, 18.8±0.2, 20.4±0.2, 20.6±0.2, 21.2±0.2, 21.7±0.2, 21.9±0.2, 22.1±0.2, 22.4±0.2, and 23.4±0.2.
10. The method of claim 1 , wherein the crystalized compound of formula I has a powder X-ray diffraction pattern comprises at least fifteen 2θ angle values selected from the group consisting of 8.1±0.2, 11.6±0.2, 12.0±0.2, 13.9±0.2, 14.8±0.2, 16.0±0.2, 18.2±0.2, 18.8±0.2, 20.4±0.2, 20.6±0.2, 21.2±0.2, 21.7±0.2, 21.9±0.2, 22.1±0.2, 22.4±0.2, and 23.4±0.2.
11. The method of claim 1 , wherein the crystalized compound of formula I has a powder X-ray diffraction pattern comprises 2θ angle values selected from 8.1±0.2, 11.6±0.2, 12.0±0.2, 13.9±0.2, 14.8±0.2, 16.0±0.2, 18.2±0.2, 18.8±0.2, 20.4±0.2, 20.6±0.2, 21.2±0.2, 21.7±0.2, 21.9±0.2, 22.1±0.2, 22.4±0.2, and 23.4±0.2.
12. The method of claim 11 , wherein the crystalized compound of formula I bas the following lattice parameters: a=8.85 ű0.01 Å, b=11.43 ű0.01 Å, c=11.96 ű0.01 Å, α=65.26°±0.01°, β=77.82°±0.01°, γ=72.60°±0.01° and volume=1043 Å 3 ±1 Å 3 .
13. The method of claim 1 , wherein the crystalized compound of formula I has a melting point of between 120° C.±2° C.