Authors:
U. GriesserUniversity of Innsbruck Institute of Pharmacy, Ph. Technology Innrain 52 6020 Innsbruck Austria Innrain 52 6020 Innsbruck Austria

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D. WeigandUniversity of Innsbruck Institute of Pharmacy, Department of Pharmaceutical Technology/ Department of Pharmacognosy Innrain 52 A-6020 Innsbruck Austria Innrain 52 A-6020 Innsbruck Austria

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J. RollingerUniversity of Innsbruck Institute of Pharmacy, Department of Pharmaceutical Technology/ Department of Pharmacognosy Innrain 52 A-6020 Innsbruck Austria Innrain 52 A-6020 Innsbruck Austria

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M. HaddowUniversity of Innsbruck Institute of Pharmacy, Department of Pharmaceutical Technology/ Department of Pharmacognosy Innrain 52 A-6020 Innsbruck Austria Innrain 52 A-6020 Innsbruck Austria

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E. GstreinUniversity of Innsbruck Institute of Pharmacy, Department of Pharmaceutical Technology/ Department of Pharmacognosy Innrain 52 A-6020 Innsbruck Austria Innrain 52 A-6020 Innsbruck Austria

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Abstract  

Five crystal polymorphs of the herbicide metazachlor (MTZC) were characterized by means of hot stage microscopy, differential scanning calorimetry, IR- and Raman spectroscopy as well as X-ray powder diffractometry. Modification (mod.) I, II and III can be crystallized from solvents and the melt, respectively, whereas the unstable mod. IV and V crystallize exclusively from the super-cooled melt. Based on the results of thermal analysis and solvent mediated transformation studies, the thermodynamic relationships among the polymorphic phases of metazachlor were evaluated and displayed in a semi-schematic energy/temperature-diagram. At room temperature, mod. III (Tfus =76C, ΔfusHIII =26.6 kJ mol-1) is the thermodynamically stable form, followed by mod. II (Tfus =80C, ΔfusHII =23.0 kJ mol-1) and mod. I (Tfus =83C, ΔfusHII=19.7 kJ mol-1). These forms are enantiotropically related showing thermodynamic transition points at ~55C (Ttrs, III/II), ~60C (Ttrs, III/I) and ~63C (Ttrs, II/I). Thus mod. I is the thermodynamically stable form above 63C, mod. III below 55C and mod. II in a small window between these temperatures. Mod. IV (Tfus =72-74C, ΔfusHII =18.7 kJ mol-1) and mod. V (Tfus =65C) are monotropically related to each other as well as to all other forms. The metastable mod. I and II show a high kinetic stability. They crystallize from solvents, and thus these forms can be present in commercial samples. Since metazachlor is used as an aqueous suspension, the use of the metastable forms is not advisable because of a potential transformation to mod. III. This may result in problematic formulations, due to caking and aggregation.

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Journal of Thermal Analysis and Calorimetry
Language English
Size A4
Year of
Foundation
1969
Volumes
per Year
1
Issues
per Year
24
Founder Akadémiai Kiadó
Founder's
Address
H-1117 Budapest, Hungary 1516 Budapest, PO Box 245.
Publisher Akadémiai Kiadó
Springer Nature Switzerland AG
Publisher's
Address
H-1117 Budapest, Hungary 1516 Budapest, PO Box 245.
CH-6330 Cham, Switzerland Gewerbestrasse 11.
Responsible
Publisher
Chief Executive Officer, Akadémiai Kiadó
ISSN 1388-6150 (Print)
ISSN 1588-2926 (Online)

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Author:
J. Davidovits