Solubility of the Pesticide Monuron in Organic Nonelectrolyte Solvents. Comparison of Observed Versus Predicted Values Based upon Mobile Order Theory

Fina, Karina M. De; Sharp, Tina L.; Chuca, Ivette; Spurgin, Michael A.; Acree, William E.; Green, Caroline E; Abraham, Michael H.

doi:10.1080/0031910021000004847

Cited by 20 publications

(15 citation statements)

References 31 publications

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“…13,27,28 A prediction based upon MOT for the solubility of diuron in 28 nonalcoholic solvents provided reasonable estimates with an average absolute deviation of 2.3%. The same authors, 13 using the LSER solvation equation, correlated the solubilities of diuron in 22 solvents with an average percentage error of 1.1%.…”

Section: Introductionmentioning

confidence: 99%

“…For monuron solubilities in 25 solvents, the error was 1.1%; the corresponding result using MOT for 21 solvents was 2.4%. 28 As already mentioned, MOT methodology has been used extensively in the prediction of solubility. The solubility of pyrene was predicted with a 2.4% average absolute deviation for a set of 30 organic solvents.…”

Section: Introductionmentioning

confidence: 99%

“…The solutes studied include anthracene, 15 phenanthrene, 9 pyrene, 16 acenaphthene, 17 fluoranthene, 18 trans-stilbene, 19,20 benzil, 21 thianthrene, 22 thioxanthen-9-one, 23 diphenyl sulfone, 24 hexachlorobenzene, 9 ferrocene, 25 4-nitroaniline and 4-nitro-N,N-dimethylaniline, 26 and diuron 27 and monuron. 28 The MOT is based on a thermodynamic treatment of the liquid state that includes terms for describing the effects that solute-solvent, solventsolvent, and solute-solute interactions have on the chemical potential of the dissolved solute. MOT assumes that hydrogenbonded aggregates are formed temporarily without a distinguishable thermodynamic identity.…”

Section: Introductionmentioning

confidence: 99%

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A General Treatment of Solubility. 2. QSPR Prediction of Free Energies of Solvation of Specified Solutes in Ranges of Solvents

Katritzky

Oliferenko²,

Oliferenko³

et al. 2003

J. Chem. Inf. Comput. Sci.

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As part of our general QSPR treatment of solubility (started in the preceding paper), we now present quantitative relationships between solvent structures and the solvation free energies of individual solutes. Solvation free energies of 80 diverse organic solutes are each modeled in a range from 15 to 82 solvents using our CODESSA PRO software. Significant correlations (in terms of squared correlation coefficient) are found for all the 80 solutes: the best fit is obtained for n-propylamine (R 2 ) 0.996); the lowest R 2 corresponds to toluene (0.604).

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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A General Treatment of Solubility. 2. QSPR Prediction of Free Energies of Solvation of Specified Solutes in Ranges of Solvents

Katritzky

Oliferenko²,

Oliferenko³

et al. 2003

J. Chem. Inf. Comput. Sci.

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“…Predicted volume fraction solubilities based upon Equations (9) and (12) Numerical values of KO; (stability constant) used were: KO; =2.2 1 0-3 m3/mol for methanol, Koi =4.0 1 0-3 m3/mol for ethanol and 2-propanol; Koi = 6.0 1 0-3 m3/mol for 1 -propanol, Koi =7.0 1 0-3 m3/mol for 1 -butanol; Koi = 8.0 1 0-3 m3/mol for 2-butano1, Koi =9.5 1 0-3 m3/mol for 1 -pentanol; KOi = 14.0 1 0-3 m3/mol for 2-methyl-1 -propanol, Koi =14.0 1 0-3 m3/mol for 1 -hexanol and 1 -heptanol and Koi =14.0 1 0-3 m3/mol for 1 -0ctanol and 1 -decanol. Tables 1 and 2 give the calculated solubilities of the diuron and monuron, respectively, using UNIFAC and Modified UNIFAC (Dortmund) in a series of organic solvents together with the experimental values measured by De Fina et al (2000 and2001). Looking at the estimated solubility data one must take into account that many of these particular systems are highly nonideal, and that the experimental solubility data cover over a 1 000-fold range in mole fraction.…”

Section: Mobile Order Theorymentioning

confidence: 99%

“…A comparison between the computed solubilities obtained here and values calculated by the mobile order theory (De Fina et al, 2000 and2001) will be given.…”

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confidence: 97%

Calculation of solubilities of the pesticides diuron and monuron in organic nonelectrolyte solvents using UNIFAC and modified UNIFAC (dortmund) models

2002

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olid-liquid equilibrium data of organic nonelectrolyte systems are becoming increasingly important in the biochemical and pesticide S industry, both regarding optimisation of the production, control and minimization of environmental impact. Despite efforts by experimentalists and scientific organisations, both in terms of new experimental measurements and critically evaluated data compilations, there still exist numerous systems for which solubility data are not readily available. To address this problem, researchers have turned to group contribution methods and semi-empirical expressions to predict desired quantities. Even though the group contribution method of UNIFAC (Fredenslund et al., 1975; Fredenslund et al., 1977) earlier showed its potential for calculating solid-equilibria (Cmehling et al., 1978), no thorough work using UNIFAC to estimate solubilities for pesticides has been published yet. This is interesting, especially that both the UNIFAC (Hansen et al., 1991) and the Modified UNIFAC (Dortmund) (Weidlich et al., 1987;Cmehling et al., 1998) have been revised recently, and are now covering a wide range of functional groups.To increase the solubility database available for developing group contribution methods, we report diuron and monuron solubilities at 25°C in different organic solvents of varying polarity and hydrogen bonding capability. Diuron and monuron are substituted urea herbicides used to control a wide variety of annual and perennial broadleaf and grassy weeds. It is used to control weeds and mosses in non-crop areas and among many agricultural crops such as fruit, cotton, sugar cane and legumes. Trade names for products containing diuron or monuron include Crisuron, Diater, Karmex and Unidron. It is often used in combination with other pesticides such as bromacil and hexazione. The solubility of diuron (3-(3,4-dichlorophenyl)-l, 1 -dimethyl urea) and monuron (3-(4-chlorophenyl)-l, 1 -dimethyl urea) in 49 and 43 different organic nonelectrolyte solvents, respectively, have been calculated. It was found that Modified UNIFAC described well the solubilities both in polar solvents like alcohols, ketones, esters and ethers and in nonpolar solvents like alkanes and aromatic hydrocarbons. UNIFAC and the mobile order theory supplement each other well in calculating the solubilities, which means that one can choose the right model depending on the solvent one is using.On a calcule la solubilite du diuron (3-(3.4-dichlorophkny1)-1, 1 -dirnethyluree) et Thermodynamic BackqroundA possible and often-used description of solid-liquid equilibrium between a liquid solvent (1) and a solid solute (2) is given by the following relation between the activity coefficient of the solute, yz, the solubility of the solute, x2, the enthalpy of fusion, AH, the melting temperature of the solute, T, and the equilibrium temperature, T: 530

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Development of Abraham model correlations for solvation characteristics of secondary and branched alcohols

Sprunger

Achi

Pointer

et al. 2010

Fluid Phase Equilibria

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Data have been compiled from the published literature on the partition coefficients of solutes and vapors into the anhydrous secondary and branched alcohols (2-propanol, 2-butanol, 2-methyl-1-propanol, 2-methyl-2-propanol and 3-methyl-1-butanol) from both water and from the gas phase. The logarithms of the water-to-alcohol partition coefficients (log P) and gas-toalcohol partition coefficients (log K) were correlated with the Abraham solvation parameter model. The derived correlations described the observed log P and log K values to within average standard deviations of 0.14 and 0.13 log units, respectively. The predictive abilities of the each correlation were assessed by dividing databases into a separate training set and test set.

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Solubility of the Pesticide Monuron in Organic Nonelectrolyte Solvents. Comparison of Observed Versus Predicted Values Based upon Mobile Order Theory

Cited by 20 publications

References 31 publications

A General Treatment of Solubility. 2. QSPR Prediction of Free Energies of Solvation of Specified Solutes in Ranges of Solvents

A General Treatment of Solubility. 2. QSPR Prediction of Free Energies of Solvation of Specified Solutes in Ranges of Solvents

Calculation of solubilities of the pesticides diuron and monuron in organic nonelectrolyte solvents using UNIFAC and modified UNIFAC (dortmund) models

Development of Abraham model correlations for solvation characteristics of secondary and branched alcohols

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