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Figure 1.

Molecular structures.

Bentazon (A) and CD derivative (B), where R is H, 2-hydroxypropyl (CH2CHOHCH3) or sulfobutylether ((CH2)4 SO3 Na) for βCD, HPCD and SBECD, respectively.

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Figure 1 Expand

Figure 2.

Electrochemical oxidation of bentazon.

(A) Differential pulse voltammetry curves for 5.0×10−4 M Btz in buffer phosphate pH 6.0 in the absence and presence of different HPCD concentrations. Curves 1–10: 0, 2, 4, 6, 8, 10, 12, 14, 20 and 30 mM HPCD; (B) Current dependence on the concentration of HPCD for bentazon in buffer phosphate pH 6.0. Current values obtained from DPV measurements. Inset: Plot of 1/[CD] versus 1/(1-I/I0) for bentazon in buffer phosphate pH 6.0.

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Figure 2 Expand

Figure 3.

Determination of the stoichiometry of the complex.

Continuous variation plot (Job plot) of the absorption change in dependence of the bentazon mole fraction.

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Figure 3 Expand

Figure 4.

FT-IR spectra.

(a) Bentazon, (b) βCD, (c) Btz-βCD (PM), (d) Btz/βCD (KN), (e) Btz/βCD (FD).

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Figure 4 Expand

Figure 5.

FT-IR spectra.

(a) Bentazon, (b) HPCD, (c) Btz-HPCD (PM), (d) Btz/HPCD (KN), (e) Btz/HPCD (FD).

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Figure 5 Expand

Figure 6.

FT-IR spectra.

(a) Bentazon, (b) SBECD, (c) Btz-SBECD (PM), (d) Btz/SBECD (KN), (e) Btz/SBECD (FD, 1∶1), (f) Btz/SBECD (FD, 1∶2).

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Figure 6 Expand

Table 1.

FT-IR spectrum assignments for Btz.

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Table 1 Expand

Figure 7.

XRD patterns.

(A) Bentazon, (B) HPCD and (C) Btz/HPCD inclusion complex (KN).

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Figure 7 Expand

Figure 8.

Thermal stability of free molecules and the inclusion complex.

DTA thermogram of (a) bentazon, (b) HPCD and (c) Btz/HPCD inclusion complex (KN).

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Figure 8 Expand

Table 2.

Thermal decomposition temperature obtained by DTA.

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Table 2 Expand

Figure 9.

Photodegradation of bentazon.

Btz photodegradation profiles in distilled water and in the presence of different cyclodextrins. Bentazon (•), Btz/βCD (▴), Btz/SBECD (○), and Btz/HPCD (▪).

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Figure 9 Expand

Figure 10.

Phase solubility diagram.

Concentration of bentazon against increasing concentrations of HPCD.

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Figure 10 Expand

Figure 11.

Dissolution test.

Dissolution profiles in water of bentazon (•), Btz/βCD (KN) (▴), Btz/SBECD (KN)* (○), and Btz/HPCD (KN) (▪). (*: inclusion complex and free bentazon mixture).

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Figure 11 Expand

Table 3.

Surface tension (γ) of water and aqueous solutions of systems under study.

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Table 3 Expand