Polymorphs of 3-difluoromethyl-1-methyl-1 H-pyrazole-4-carboxylic acid (9-dichloro-methylene-1,2,3,4-tetrahydro-1,4-methano-naphthalen-5-yl)-amide

Patent metadata

Field	Value
Publication number	US-9617219-B2
Application number	US-201515121081-A
Country	US
Kind code	B2
Filing date	Feb 24, 2015
Priority date	Feb 27, 2014
Publication date	Apr 11, 2017
Grant date	Apr 11, 2017

Abstract

The present invention relates to solid forms of the fungicide of formula (I): compositions comprising the solid forms and methods of their use as fungicides.

First claim

The invention claimed is:

1. A hydrated crystalline polymorph of the compound of formula I

which has a powder X-ray diffraction pattern comprising at least three d values selected from the group consisting of 10.45 ±0.2, 7.45±0.2, 6.71±0.2, 6.31±0.2, 5.99±0.2, 5.42±0.2, 5.23±0.2, 4.78±0.2, 4.60±0.2, 4.53±0.2, 4.33±0.2, 4.14±0.2, 3.97±0.2, 3.86±0.2, 3.73±0.2, 3.62±0.2, 3.49±0.2, 3.37±0.2, 3.30±0.2, 3.23±0.2, 3.19±0.2, 3.14±0.2, 3.06±0.2 and 3.00±0.2 and which has no peak in the powder X-ray diffraction pattern at d=16.58±0.2 and d =16.84±0.2.

2. The crystalline polymorph of claim 1 , which has the following lattice parameters: a=18.28(5 ), b=12.65(5 ), c=7.81(5 ), α=90.00 , β=90.00 , Υ=90.00 and volume=1805.0(5) Å 3 .

3. The crystalline polymorph of claim 1 , which is a monohydrate containing 4.3 ±0.2% w/w water.

4. The crystalline polymorph of claim 1 , which has a dehydration/melting point of between 80 and 125° C.

5. An agricultural composition comprising a polymorph as claimed in claim 1 and at least one agriculturally acceptable carrier or diluent.

6. The composition of claim 5 , which comprises at least one further fungicide.

7. The composition of claim 6 , wherein the further fungicide is a strobilurin or an azole.

8. A method of preventing or controlling fungal infection on plants or plant propagation material comprising treating the plant or plant propagation material with a fungicidally effective amount of an agricultural composition of claim 5 .

Assignees

• Syngenta Participations Ag

Inventors

• Hone John
• Jones Ian Kevin
• George Neil

Classifications

• C07B2200/13

  Crystalline forms, e.g. polymorphs · CPC title

• C07D231/14 Primary

  with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms · CPC title

• A01N45/02 Primary

  having three carbocyclic rings · CPC title