Enhanced process efficiency through the novel use of dispersants and processes for producing phthalimide based fungicide

Abstract

The present invention provides a water-based dispersion comprising (a) nitrogen compound selected from 3a,4,7,7a-Tetrahydro-1H-isoindole-1,3(2H)-dione and 1,3- Dihydro-2H-isoindole-1,3-dione and (b) sulfonate-based dispersant, and further provides a process for producing phthalimide based fungicide which comprises (1) preparing a water-based dispersion comprising (a) nitrogen compound such as 3 a, 4, 7,7a- Tetrahydro- 1H-isoindole-1,3 (2H)-dione and 1, 3 -Dihydro-2H-i soindole-1,3- dione and (b) sulfonate-based dispersant, (2) reacting the dispersion of step (1) with aqueous alkaline solution, (3) reacting the resulting salt with mercapto-based compound selected from perchloromethyl mercaptan (PCMM) and pentachloro ethyl mercaptan (PCEM) to obtain phthalimide based fungicide such as folpet, captan and / or captafol.

Description

[0001] ENHANCED PROCESS EFFICIENCY THROUGH THE NOVEL USE OF DISPERSANTS AND PROCESSES FOR PRODUCING PHTHALIMIDE BASED FUNGICIDE

[0002] Throughout this application various publications are referenced. The disclosures of these documents in their entireties are hereby incorporated by reference into this application in order to more fully describe the state of the art to which this invention pertains.

[0003] FIELD OF THE INVENTION

[0004] The invention is in the field of synthetic chemistry, and in particular the field of pesticide synthetic chemistry. Skills and materials from different and distinct fields of art are novelly exploited for the first time in synthetic chemical processes.

[0005] The invention is in the field of processes for producing phthalimide based fungicide. The present invention introduces significant improvements in the preparation of imide-based fungicides which are prepared in processes including a step of preparing (water-soluble), salts of an imide by reacting a slurry of Imide particles with an alkaline aqueous solution.

[0006] Discussion

[0007] The present invention introduces significant improvements in the preparation of salts of an imide through the strategic incorporation of dispersants, such as lignosulfonates, into the imide slurry formulation. Unlike conventional processes that rely on mechanical agitation and high-shear mixing alone, the inclusion of dispersants fundamentally enhances the dispersion and stability of the imide particles in aqueous media, leading to a series of process advantages that were previously unattainable.

[0008] Water-soluble salts of an imide are used in a reaction to prepare imide-based fungicides. Thus, the present invention introduces significant improvements in the preparation of imide-based fungicides which are made from those salts of an imide.

[0009] The present invention concerns improved methods for the preparation of synthetic intermediates useful in the synthesis of phthalimide based fungicides. In particular, the present invention concerns improved methods for the preparation of salts of nitrogen compounds such as salts of 3a,4,7,7a-Tetrahydro-lH-isoindole-l,3(2H)-dione and salts of 1,3 -Dihy dro-2H-i soindole- 1 , 3 -di one.

[0010] The present invention provides a process for producing phthalimide based fungicide synthetic intermediate which comprises (1) preparing a water-based dispersion comprising (a) nitrogen compound selected from 3a,4,7,7a-Tetrahydro-lH-isoindole- l,3(2H)-dione and l,3-Dihydro-2H-isoindole-l,3-dione and (b) a dispersant, particularly a sulfonate-based dispersant, (2) reacting the dispersion of step (1) with aqueous alkaline solution. The salt that results from this improved process is then carried on to further synthetic steps, exemplified by the following steps, (3) reacting the resulting salt with mercapto-based compound selected from perchloromethyl mercaptan (PCMM) and pentachloro ethyl mercaptan (PCEM) and most commonly, (4) isolation the phthalimide based fungicide such as Captan, Folpet and Captafol. An anti -foam agent can be added either in step (1) or in step (2).

[0011] The present invention thus clearly also provides a novel reactant intermediate mixture a.k.a. a dispersed reactant mixture, useful in improving the efficiency and yield of processes to obtain salts of 3a,4,7,7a-Tetrahydro-lH-isoindole-l,3(2H)-dione and salts of l,3-Dihydro-2H-isoindole-l, 3-dione by reacting the novel reactant intermediate mixture with aqueous alkaline solution. Ultimately the improvement in the process to provide the above-mentioned salts also provides improved yields of phthalimide fungicides made from them.

[0012] The novel reactant mixture, (dispersed reactant mixture), is an aqueous dispersion of finely divided solid particles of 3a,4,7,7a-Tetrahydro-lH-isoindole-l,3(2H)-dione or of l,3-Dihydro-2H-isoindole-l, 3-dione and a dispersant, particularly a sulfonate-based dispersant, such as a lignosulphonate. The finely divided solid particles of 3a, 4, 7,7a- Tetrahydro-lH-isoindole-l,3(2H)-dione or of l,3-Dihydro-2H-isoindole-l, 3-dione are characterized by a particle size distribution such that the D50 (median) value is 50 micron or less, or more typically between about 0.1pm to about 50 pm typically about 1pm to about 50pm.

[0013] The nitrogen compound selected from 3a,4,7,7a-Tetrahydro-lH-isoindole-l,3(2H)- dione and l,3-Dihydro-2H-isoindole-l, 3-dione is sometimes conveniently referred to in this disclosure as an Imide. Similarly, for the sake of convenience the water-based dispersion or suspension comprising nitrogen compound selected from 3a,4,7,7a-Tetrahydro-lH-isoindole- l,3(2H)-dione and l,3-Dihydro-2H-isoindole-l, 3-dione and a dispersant, is sometime referred to herein as a Slurry or an Imide Slurry, for the sake of convenience.

[0014] The salt that is produced by reacting the inventive dispersion or suspension of nitrogen compound (Imide Slurry), selected from 3a,4,7,7a-Tetrahydro-lH-isoindole-l,3(2H)- dione and l,3-Dihydro-2H-isoindole-l, 3-dione (Imide), and a dispersant (sulphonate- based dispersant), with aqueous alkaline solution is sometimes referred to herein as an Imide Salt, Sodium Imide Salt, or sometimes water-soluble Sodium Imide salt.

[0015] Thus, the entire process that includes the improved process of producing the salt as well reacting with mercapto-based compounds is also an embodiment of this invention as the improvements in efficacy and simplicity of producing the synthetic salt intermediate also improves the efficacy, simplicity and increases the yield of the phthalimide based fungicide produced from these salts of nitrogen compounds. The entire process for producing the phthalimide based fungicide via the improved process for producing the salt of the nitrogen compound, typically includes a step of removing the (sulfonate- based), dispersant (and anti-foam agent), so that the isolated phthalimide based fungicide obtained in step (4) is largely free of measurable quantities.

[0016] Incidentally, before isolation and purification steps are conducted, the process produces solid phthalimide fungicide, intimately associated with sulphonate-based dispersant, such as lignosulphonate, wherein intimately associated, denotes association more intimate than achieved through simple mixing of the phthalimide fungicide with the dispersant.

[0017] BACKGROUND AND SUMMARY

[0018] Captan, (N-(trichloromethylthio)-3a,4,7,7a-tetrahydrophthalimide, Captafol (N- [l,l,2,2-tetrachloroethylthiol]-4-cyclohexene-l,2-dicarboximide; and Folpet N- (Trichloromethylthio)phthalimide, are phthalimide-based fungicides having a broadspectrum of fungicidal activity.

[0019] Some synthetic processes are known as disclosed in US2,553,770, US2,553,771, US2,553,776 and US3, 314,969, where the process includes a reaction of phthalimide compound and derivative thereof with mercapto-based compound such as perchloromethyl mercaptan (PCMM) and pentachloro ethyl mercaptan (PCEM)

[0020] To achieve high phthalimide-based fungicide assay and yield, reaction of the phthalimide and derivative thereof is conducted under basic conditions, with optionally, excess amount of mercapto based compound but there is still a need to develop a simple and efficient process for increasing the yield of the reaction.

[0021] The present invention introduces significant improvements in the preparation of imide-based fungicides through the strategic incorporation of dispersants, such as lignosulfonates, into the imide slurry formulation which is an important intermediate mixture for preparing imide salts. In general the imide salts that are prepared by the improved inventive processes and equipment herein disclosed are reacted with further reactants to produce imide-based fungicide compounds as detailed later.

[0022] Unlike conventional processes that rely on mechanical agitation and high-shear mixing alone to prepare a slurry of solid imide particles, the inclusion of dispersants into the (aqueous), slurry of imide particles fundamentally enhances the dispersion and stability of the imide particles in aqueous media and particularly the slurry used in the reaction with aqueous alkaline solutions, leading to a series of process advantages that were previously unattainable. The inventive processes of the invention include novel uses of dispersants and processing equipment and suggests further optimization possibilities made possible by the invention. The possibility of beneficially introducing additional ingredients into the imide slurry of the invention such as antifoam agents is clearly part of the inventive concept.

[0023] Innovation in Dispersant Utilization,

[0024] Dispersants have been historically employed in various industrial applications including formulation technologies of finished forms of pharmaceutical, agrochemical and pesticide products. However, the use of these types of dispersants in chemical syntheses of active ingredient chemicals, and in particular, the use of dispersants in the early stages of imide slurry preparation for imide-based fungicide synthesis has not been previously disclosed and never previously optimized for this type of use. Some commonly known Imide-based fungicide compounds include Captan, Folpet and Captafol. In conventional methods of forming Imide slurry of solid imide in aqueous media, the imide particles tend to aggregate, leading to high slurry viscosity, non-uniform particle distribution, and the risk of pipeline clogging in manufacturing equipment.

[0025] The novel approach described herein mitigates these issues by ensuring a more homogeneous and low-viscosity imide slurry, significantly improving downstream processing efficiency.

[0026] While not being bound by any theory, it is apparent that the dispersants used in these inventive slurries and processes, exemplified by lignosulfonates, function inter alia, by reducing inter-particle attraction, thereby maintaining the solid imide particles in a finely dispersed state. This prevents sedimentation and blockages within equipment and piping and particularly, in continuous process flow processes, allowing for uninterrupted operation with reduced maintenance requirements. Furthermore, improved slurry flowability by incorporation of dispersant, results in more precise and consistent dosing into the subsequent reaction stages, leading to enhanced control over reaction kinetics and product quality. Persons skilled in these arts will immediately perceive further advantages and benefits of the inventive processes, equipment and products of the invention.

[0027] Differentiation from Prior Art

[0028] A review of prior reports, including patents US2,553,770A; US2,553,771; US2,553,776; GB 1389031 A; US2,713,058; US3,544,625A; and CN108467356A, indicates that while various methods for imide preparation have been explored, none have specifically disclosed the integration of dispersants at the slurry preparation stage to achieve these process benefits. The current invention thus represents a novel advancement by demonstrating that dispersants not only facilitate slurry stability but also provide cascading improvements throughout the production process.

[0029] By addressing long-standing challenges associated with imide slurry processing, this invention offers a scalable and industrially viable solution that enhances both operational efficiency and product consistency. The improved process represents a critical innovation in fungicide manufacturing, leading to a superior and more cost- effective production methodology. Besides any of the myriad other surprising aspects, the adoption of dosage form formulating techniques and materials and their employment in the field of synthetic chemistry is in and of itself surprising as these formulating skills are rarely seen as applicable to chemical synthesis.

[0030] SUMMARY OF THE INVENTION

[0031] The present invention provides a process for producing salt(s) of nitrogen compound exemplified by 3a,4,7,7a-Tetrahydro-lH-isoindole-l,3(2H)-dione and 1,3-Dihydro- 2H-isoindole-l, 3-dione, comprising (1) preparing a water-based dispersion comprising (a) nitrogen compound selected from 3a,4,7,7a-Tetrahydro-lH-isoindole- l,3(2H)-dione and l,3-Dihydro-2H-isoindole-l, 3-dione and (b) a dispersant, particularly, a sulfonate-based dispersant, (2) reacting the dispersion of step (1) with aqueous alkaline solution to produce the salt.

[0032] The present invention provides a process for producing salt of nitrogen compound selected from a group comprising 3a,4,7,7a-Tetrahydro-lH-isoindole-l,3(2H)-dione and l,3-Dihydro-2H-isoindole-l, 3-dione, the process comprising (1) preparing a water-based dispersion of solid particles comprising (a) nitrogen compound such as, 3a,4,7,7a-Tetrahydro-lH-isoindole-l,3(2H)-dione and / or l,3-Dihydro-2H-isoindole- 1, 3-dione and (b) sulfonate-based dispersant, (2) reacting the dispersion of step (1) with aqueous alkaline solution, wherein the solid particles of nitrogen compound beneficially have a particle size distribution characterized by a D50 (median), value of about 50 microns or less when the dispersion of particles is reacted with the aqueous alkaline solution to form the salt. Small particle sizes are beneficial.

[0033] The present invention further provides a process for producing phthalimide based fungicide exemplified by folpet, captan and captafol, which comprises (1) preparing a water-based dispersion of solid particles comprising (a) nitrogen compound selected from 3a,4,7,7a-Tetrahydro-lH-isoindole-l,3(2H)-dione and 1,3-Dihydro-2H- isoindole-1, 3-dione and (b) a preferably, sulfonate-based dispersant, (2) reacting the dispersion of step (1) with aqueous alkaline solution, and then (3) reacting the resulting salt with mercapto-based compound such as perchloromethyl mercaptan (PCMM) and pentachloro ethyl mercaptan (PCEM) and (4) isolation the phthalimide based fungicide.

[0034] The present invention in some embodiments, further provides a novel reactant intermediate mixture useful in improving the efficiency and yield of processes to obtain salts of 3a,4,7,7a-Tetrahydro-lH-isoindole-l,3(2H)-dione, and salts of 1,3- Dihydro-2H-isoindole-l, 3-dione (Imide Salts), by reacting the novel reactant intermediate mixture with aqueous alkaline solution. The novel reactant mixture is an aqueous dispersion or suspension of preferably, finely divided solid particles of nitrogen compounds which are either or both of 3a,4,7,7a-Tetrahydro-lH-isoindole-l,3(2H)-dione or of l,3-Dihydro-2H-isoindole- 1, 3-dione and a dispersant, particularly a sulfonate-based dispersant, such as a lignosulphonate (a.k.a. Imide Slurry).

[0035] In some embodiments the present invention provides a novel “reaction combination” (reaction mixture) contained in a “reaction space”, from which Imide Salts, are obtained. The reaction combination comprises the components, a. finely divided solid Imide particles of 3a,4,7,7a-Tetrahydro-lH-isoindole-l,3(2H)-dione, and / or 1,3- Dihydro-2H-isoindole-l, 3-dione, dispersed in b. aqueous media, further comprising c. sulphonate-based dispersant and d. dissolved base. The reaction combination components react in the reaction space to provide aqueous solution of water-soluble salts of 3a,4,7,7a-Tetrahydro-lH-isoindole-l,3(2H)-dione, and / or water-soluble salts of l,3-Dihydro-2H-isoindole-l, 3-dione. In some embodiments the novel reaction combination (reaction mixture) contained in a reaction space further comprises an antifoam agent such as, a poly dimethyl siloxane oil - based antifoam agent.

[0036] In some embodiments the reaction space for reaction of the reaction combination, comprises a vessel equipped with mixing, stirring or agitation capability preferably being equipped so as to provide vigorous interaction between the components of the reaction combination components sufficient to effect completion of reaction between the finely divided solid Imide particles and the dissolved base, such as alkali metal hydroxide or a metal salt of carbonate, exemplified herein by Sodium Hydroxide.

[0037] In some embodiments the reaction space for the reaction of the components of reaction combination, is equipped with high shear mixing equipment. In some embodiments the reaction space for the reaction of the reaction combination, is equipped with high shear mixing equipment and pumping capability.

[0038] In some embodiments the reaction space for the reaction of the components of reaction combination, is the internal space within one or more high shear pumps. In this form of highly optimized embodiment, the components of the reaction combination are introduced together or as separate components into the reaction space, the solid imide is combined with the sulphonate-based dispersant, the solid imide is reduced to fine particles, the fine particles are brought into contact with the dissolved base and the resultant water-soluble Imide Salts are obtained as an aqueous solution in the water of the aqueous media and pumped out of the internal space from the high shear pump. The pumped-out solution of Imide Salts may optionally be recirculated through the high shear pump, and / or transmitted to a further pump and / or transmitted for subsequent reaction with mercapto-based compounds selected from perchloromethyl mercaptan (PCMM) and pentachloro ethyl mercaptan (PCEM) PCMM to obtain phthalimide fungicide compounds.

[0039] In some embodiments the “reaction space” for the reaction of the components of reaction combination, is equipped with high shear mixing equipment. In some embodiments the reaction space for the reaction of the reaction combination, is equipped with high shear mixing equipment and pumping capability.

[0040] In some embodiments the reaction space for the reaction of the components of reaction combination, is an area of space within which the components of the reaction combination are into contact and the resultant water-soluble Imide Salts are obtained as an aqueous solution in the water of the aqueous media.

[0041] Solely for the purpose of illustration of the possible scope of this concept, a system is described where. A liquid stream of a slurry of finely divided particles of a. Imide particles (e.g., 3a,4,7,7a-Tetrahydro-lH-isoindole-l,3(2H)-dione, and / or 1,3-Dihydro- 2H-isoindole-l, 3-dione), dispersed in b. aqueous media further comprising c. sulphonate-based dispersant is impinged on or with, a stream of an aqueous solution of base (e.g., NaOH) optionally in the presence of antifoam agent, and the reaction between the components occurs in the area of space where both streams converge and impinge. This area of space is also understood to be the defined “reaction space”. The (preferably) finely divided solid particles of 3a,4,7,7a-Tetrahydro-lH-isoindole- l,3(2H)-dione or the preferably finely divided solid particles of 1,3-Dihydro-2H- isoindole-1, 3-dione are preferably characterized by a particle size distribution such that the D50 (median) value is 50 micron or less, or more typically between about 0.1pm to about 50 pm. The sulphonate-based dispersant is exemplified by Lignosulphonates such as by the acidic lignosulfonate Reax® 88A. REAX 88A is a commercially available sodium salt of a chemically modified low molecular weight kraft lignin polymer solubilized by five sulfonate groups (Ingevity). As should be clear, the desired fine particle size distribution of the imides, 3a, 4, 7,7a- Tetrahydro-lH-isoindole-l,3(2H)-dione or l,3-Dihydro-2H-isoindole-l, 3-dione can be achieved either, i. by processing a slurry of larger particles optionally already combined with dispersant prior to or simultaneously with reaction with aqueous alkaline solution, or in the alternative, ii. solid imide, 3a,4,7,7a-Tetrahydro-lH-isoindole-l,3(2H)-dione or solid imide, l,3-Dihydro-2H-isoindole-l, 3-dione can be obtained as a finely divided solid particulate(s) and combined as such with dispersant and aqueous media such as water to obtain the inventive Imide Slurry for use in the inventive process.

[0042] In either case, as with many of the other embodiments illustrated herein, the dispersion or suspension of imide particles and dispersant can further include an antifoam ingredient.

[0043] In some other embodiments, as mentioned, an antifoam agent is introduced into the “reaction space” wherein the reaction to obtain the imide salt occurs. The antifoam agent can be a component of the Imide Slurry, the Aqueous Solution of Base (e.g., NaOH solution), or introduced as a separate third component of the “reaction combination” that only encounters the imide slurry and the Aqueous Solution of Base at the time that all components of the “reaction combination” are combined in the “reaction combination”. Clearly in each of the above mentioned embodiments there will be more and less optimized examples and the invention herein described is not limited by the level to which the systems, compositions, combinations, equipment or processes conditions etc. have been optimized.

[0044] A combination of dispersed imide particles and dispersant in aqueous media is of major (though not exclusive), focus. This combination may benefit from the addition of components such as antifoam agent. The reaction of this combination with aqueous solution of base can benefit from process optimization from the point of view of reaction conditions (e.g., temperature; level of mixing intensity / shear; time, etc.); equipment, e.g. high shear mixer, rotor / stator, high shear pump (in-line or standalone), media mill (in-line or stand-alone), etc. and also how the process is incorporated into a larger process to finally prepare phthalimide fungicide compounds, including arrangements of equipment and materials for continuous or batch processing. Now that the invention and many embodiments are described, skilled artisans in these arts and in particular process engineering artisans will immediately conceive of optimization possibilities, none of these can be viewed as departing from the invention.

[0045] Similarly, the inventors are fully convinced that many varied dispersants can provide some if not all of the advantages that have been experimentally illustrated by sulphonate-based dispersants and in particular Lignosulphonate salts.

[0046] The principle action as a dispersant of solid particles in aqueous media would be a reasonable initial criteria for choice of candidate dispersants, and the selection of optimum, brands, types and grades co-formulants such as dispersant compounds is the very essence of the skill set of a formulator of dispersed systems, suspensions dispersions etc.

[0047] The difficulty in immediately identifying a single individual as an audience for this disclosure highlights one surprisingly inventive aspect to the invention. The “problem” requiring a solution is a purely “synthetic chemistry” problem. The range of “solutions” to that problem herein provided comes from the field of finished pesticide composition formulation. Typically, the skills of the composition formulator are considered irrelevant to the issues encountered in improvements of synthetic processes. Further, given the normally encountered industrial environment synthetic chemists and formulation engineers are unlikely to cooperate or perhaps ever even meet.

[0048] As one of the central focus areas of the invention is an aqueous dispersion / suspension of bioactive or agrochemical chemical particles, it is likely that the “skilled person” or artisan, in this invention to which this disclosure is directed team that comprises a formulator or formulation chemist just as much as the disclosure is directed to a team including chemical synthetic chemist and / or or industrial process engineer. It is conceivable that this invention should be seen as directed to a team of individuals who each provide some of the skill set that encompasses the invention across its embodiments. While some aspects of the invention are only the purview of Formulation Engineers others are easy to understand only by the synthetic chemistry team members while still further aspects and embodiments will spark optimization possibilities only from the industrial process engineering member of the team making up the “skilled Person” or artisan. DETAILED DESCRIPTION OF THE INVENTION

[0049] Definitions

[0050] Prior to setting forth the present subject matter in detail, it may be helpful to provide definitions of certain terms to be used herein. Unless defined otherwise, all technical and scientific terms used herein have the same meaning as is commonly understood by one of skill in the art to which this subject matter belongs.

[0051] The term “a” or “an” as used herein includes the singular and the plural, unless specifically stated otherwise. Therefore, the terms “a,” “an” or “at least one” can be used interchangeably in this application.

[0052] Throughout the application, descriptions of various embodiments use the term “comprising”; however, it will be understood by one of skill in the art, that in some specific instances, an embodiment can alternatively be described using the language “consisting essentially of’ or “consisting of’ or containing. in general all numerical values are to be assumed to be preceded by “about” unless otherwise dictated by the context or text. The term “about” as used herein regarding numerical values, specifically includes ±10% from the indicated values in the range unless otherwise detailed or unless the context makes this clearly unusable. For example, a value preceded by “no more than” or a value “17 or less” where only one option for a 10% approximation is appropriate. In such circumstances the “limit” imposed will not cancel the concept of approximation, but it will curtail it such that it will only encompass the normally encountered errors in measurement. So that in some cases it would be understood that “about 17°C or less” would be intended to include 17.6 if a 0.6°C error margin is within the normally encountered errors associated with that same measurement.

[0053] In addition, the endpoints of all ranges directed to the same component or property herein are inclusive of the endpoints, are independently combinable, and include all intermediate points and ranges. It is understood that where a parameter range is provided, besides commonly accepted rules for rounding, all integers within that range, and tenths thereof, are also provided by the invention. For example, a range of “10- 50%” includes 9.5%, 9.6%, 9.7%, 9.8%, 9.9%, 10%, 10.1%, 10.2%, etc. up to 50.4%. Salts of nitrogen compounds 3a,4,7,7a-Tetrahydro-lH-isoindole-l,3(2H)-dione and

[0054] 1.3-Dihydro-2H-isoindole-l,3-dioneare are important intermediates for preparing phthalimide based fungicides such as folpet captan and captafol.

[0055] The present invention provides a process for producing salts of nitrogen compound selected from salts of 3a,4,7,7a-Tetrahydro-lH-isoindole-l,3(2H)-dione and salts of

[0056] 1.3-Dihydro-2H-isoindole-l, 3-dione, wherein the process comprises (1) preparing a water-based dispersion comprising (a) particulate nitrogen compound selected from 3a,4,7,7a-Tetrahydro-lH-isoindole-l,3(2H)-dione and l,3-Dihydro-2H-isoindole-l,3- dione and (b) sulfonate-based dispersant and (2) reacting the dispersion of step (1) with aqueous alkaline solution to obtain the salt. Inclusion of the dispersant compound with the particles of 3a,4,7,7a-Tetrahydro-lH-isoindole-l,3(2H)-dione and / or 1,3-Dihydro- 2H-isoindole-l, 3-dione, improves the outcomes of the process step of reacting with the aqueous alkaline solution.

[0057] In some embodiments the aqueous alkaline solution is a sodium hydroxide aqueous solution, and the salt obtained is a sodium salt.

[0058] The present invention provides a process for producing phthalimide based fungicide which comprises (1) preparing a water-based dispersion comprising (a) particulate nitrogen compound selected from 3a,4,7,7a-Tetrahydro-17 / -isoindole-l,3(2J7)-dione and l,3-Dihydro-2H-isoindole-l, 3-dione and (b) sulfonate-based dispersant compound, (2) reacting the dispersion of step (1) with aqueous alkaline solution, (3) reacting the resulting salt with mercapto-based compound such as perchloromethyl mercaptan (PCMM) and pentachloro ethyl mercaptan (PCEM) and most commonly, (4) isolation of the phthalimide based fungicide.

[0059] Typically the dispersant compound has been removed during the process so that the phthalimide based fungicide commonly isolated in step (4) no longer contains any significant amounts of dispersant.

[0060] In some embodiments, the phthalimide based fungicide is N-trichloromethylthio- tetrahydro phthalimide, also called captan.

[0061] In some embodiments, the phthalimide based fungicide is N-trichloromethylthio- phthalimide, also called folpet In some embodiments, the phthalimide based fungicide is N-trichloromethylthio- succinimide, also called NSC 13116

[0062] In some embodiments, 3a,4,7,7a-Tetrahydro-U / -isoindole-l,3(2J7)-dione is cis isomer (cis-3a,4,7,7a-Tetrahydro-U / -isoindole-l,3(2J7)-dione.)

[0063] The reacting step (3) in the above process for producing phthalimide based fungicide includes the salt of the nitrogen compound produced in step (2) being dissolved in water.

[0064] In some embodiments, the ratio between the weight of the nitrogen compound to the total volume of water for dissolving the salt obtained in step (2) is between about 1 :5 to about 1 :6.5 w / v.

[0065] In some embodiments, the term “total volume of water” refers to the volume of water used for preparing the dispersion in step 1 and the water volume of the aqueous alkaline solution when combined in step (2).

[0066] In some embodiments, when the nitrogen compound is cis-3a,4,7,7a-Tetrahydro 1H- isoindole-l,3(2J7)-dione , the ratio between the cis-3a,4,7,7a-Tetrahydro UT-isoindole- l,3(2J7)-dione salt produced in step (2), and the water is between about 1 :5 to about 1 :5.5 w / v.

[0067] In some embodiments, when the nitrogen compound is l,3-Dihydro-2H-isoindole-l,3- dione, the ratio between the l,3-Dihydro-2H-isoindole-l, 3-dione salt produced in step (2), and water is between about 1 :6 to about 1 :6.5 w / v.

[0068] In some embodiments, step (1) and / or (2) is conducted in presence of or with the addition of, antifoaming agent.

[0069] In some embodiments, step (1) and / or (2) are conducted at temperature of between about 0 to about 15°C.

[0070] In some embodiments, step (1) and / or (2) is conducted at temperature of about 0-5°C.

[0071] In some embodiments, the process is continuous process.

[0072] In some embodiments, the process is a batch process.

[0073] The present invention provides a process for producing phthalimide based fungicide which comprises (1) preparing a water-based dispersion comprising (a) nitrogen compound selected from 3a,4,7,7a-Tetrahydro-177-isoindole-l,3(277)-dione and 1,3- Dihydro-2H-isoindole-l, 3-dione and (b) sulfonate-based dispersant, (2) reacting the dispersion of step (1) with aqueous alkaline solution, (3) reacting the resulting salt with mercapto-based compound such as perchloromethyl mercaptan (PCMM), pentachloro ethyl mercaptan (PCEM) and generally, (4) isolation the phthalimide based fungicide.

[0074] The present invention provides a process for producing salts of nitrogen compounds such as 3a,4,7,7a-Tetrahydro-177-isoindole-l,3(277)-dione and 1,3-Dihydro-2H- isoindole-1, 3-dione comprising (1) preparing a water-based particulate dispersion comprising (a) nitrogen compound such as 3a,4,7,7a-Tetrahydro-177-isoindole- l,3(277)-dione and / or l,3-Dihydro-2H-isoindole-l,3-dione and (b) sulfonate-based dispersant, (2) reacting the dispersion of step (1) with aqueous alkaline solution to produce the salt.

[0075] The salt produced by the process can be a water-soluble salt such as an alkali metal salt exemplified by sodium salts. In addition to the dispersant compound, anti-foam compounds can be included in the dispersion of step (1) or the reacting step (2) mixture.

[0076] The present invention provides a process for producing salts of nitrogen compound 3a,4,7,7a-Tetrahydro-177-isoindole-l,3(277)-dione and salts of 1,3-Dihydro-2H- isoindole-1, 3-dione comprising (1) preparing a water-based dispersion comprising (a) solid particles of nitrogen compound 3a,4,7,7a-Tetrahydro-177-isoindole-l,3(277)- dione or l,3-Dihydro-2H-isoindole-l, 3-dione and (b) sulfonate-based dispersant, (2) reacting the dispersion of step (1) with aqueous alkaline solution, wherein the solid particles of nitrogen compound have a particle size distribution characterized by a D50 value of about 50 microns or less when reacted with the aqueous alkaline solution.

[0077] In previously reported comparable processes, the nitrogen compound is found to degrade during the reaction with the alkaline aqueous solution.

[0078] In some embodiments of this invention, the level of degradation of the nitrogen compound in the process to prepare the nitrogen compound salt is reduced as compared to a similar process without the use of the dispersant.

[0079] In some embodiments, the improved process that includes the sulfonate-based dispersants is characterized by a level of degradation of the nitrogen compound which is at least 5% less than a similar process which does not include a sulfonate-based dispersant.

[0080] In some embodiments of this invention, the level of degradation of the dispersed nitrogen compound in the inventive process to prepare the salt of the nitrogen compound is reduced by ensuring the dispersed particulate nitrogen compound has a fine particle size distribution and dispersant compound is included in the process.

[0081] In some embodiments, the degradation of the nitrogen compound when treated with the aqueous alkaline solution in the process to prepare the salt of the nitrogen compound is at least 5% less when the nitrogen compound is a dispersed particulate with a particle size distribution characterized by D50 of about 50 micron or less together with a sulphonate-based dispersant as compared to a similar process which does not include sulfonate-based dispersant and where the solid particles of nitrogen compound when treated with the aqueous alkaline solution, has a particle size distribution characterized by a D50 significantly more than about 50 micron.

[0082] In some embodiments, the sulfonate-based dispersant comprises a sulfonate-based dispersant comprises a lignosulfonate. In some embodiments the sulfonate-based dispersant comprises an acidic lignosulfonate. In some embodiments, the acidic lignosulfonate comprises Reax® 88A. REAX 88A is the sodium salt of a chemically modified low molecular weight kraft lignin polymer solubilized by five sulfonate groups. REAX 88A is available from (Ingevity) MeadWestvaco Corporation PO Box 118005 Charleston, SC 29423-8005.

[0083] In some embodiments, the present invention also provides a process for producing salts of cis-3a,4,7,7a-Tetrahydro-l / / -isoindole-l,3(2J7)-dione. The comprises (1) preparing a water-based dispersion comprising (a) solid particulate cis-3a,4,7,7a- Tetrahydro-17 / -isoindole-l,3(2J7)-dione and (b) a lignosulfonate and (2) reacting the dispersion of step (1) with aqueous alkaline solution. In some embodiments an antifoam agent is also included in the process.

[0084] In some embodiments, the salt of cis-3a,4,7,7a-Tetrahydro-17 / -isoindole-l,3(2J7)-dione obtained in step (2) is treated with perchloromethyl mercaptan to obtain (3aR,7aS)-2- [(Trichloromethyl)sulfanyl]-3a,4,7,7a-tetrahydro-lH-isoindole-l,3(2H)-dione. In some embodiments remnants of the lignosulphonate and any anti-foam agent used in the process are removed from the (3aR,7aS)-2-[(Trichloromethyl)sulfanyl]- 3a,4,7,7a-tetrahydro-lH-isoindole-l,3(2H)-dione.

[0085] In some embodiments, the present invention provides a process for producing salts of 17 / -isoindole-l,3(2J7)-dione. The process comprises (1) preparing a water-based dispersion comprising (a) solid particulate 17 / -isoindole-l,3(2J7)-dione and (b) a lignosulfonate and (2) reacting the dispersion of step (1) with aqueous alkaline solution.

[0086] In some embodiments an anti-foam agent is also included in the process. In some embodiments, the antifoaming agent is silicon oil-based compound. In some embodiments, the silicon-based compound is Rhodorsil® antifoam 426. Rhodorsil Antifoam 426 R [a.k.a. SILCOLAPSE® 426] is a non-ionic aqueous emulsion based on polydimethyl siloxane oil. It has 30 % active matter content and is available from Elkem (Bluestar Silicones).

[0087] In some embodiments, the salt obtained is treated with perchloromethyl mercaptan to obtain 2-[(Tricloromethyl)sulfanyl]-lH-isoindole-l,3(2H)-dione.

[0088] In some embodiments remnants of the lignosulphonate and any anti-foam agent used in the process are removed from the 2-[(Tricloromethyl)sulfanyl]-lH-isoindole- l,3(2H)-dione.

[0089] In the improved processes and methods of the invention for preparing synthetic intermediates useful in the synthesis of phthalimide based fungicides and in particular, the improved methods for the preparation of salts of nitrogen compounds such as salts of 3a,4,7,7a-Tetrahydro-lH-isoindole-l,3(2H)-dione and salts of 1,3-Dihydro-2H- isoindole-1, 3-dione, the methods typically involve a step in which any remaining traces of the sulphonate-based dispersant(s) or anti foam agent(s) are removed so as to leave the final product free of these compounds however, the scope of this invention is unaffected by inclusion or exclusion of these additional, process steps. Thus, although untypical, the inventors can envision the process of producing the salts of nitrogen compounds being performed without removal of the sulphonate-based dispersant(s) or anti foam agent(s), and continuing the next process steps to produce the phthalimide fungicide so as to obtain a novel solid form of the Phthalimide fungicide, wherein the dispersant, antifoam agent or a combination thereof are more intimately associated with molecules of the phthalimide based fungicidal active compound than would be achieved by simple admixing the compounds together.

[0090] Method and Use

[0091] The present invention provides a method for reducing the degradation rate of nitrogen compound selected from 3a,4,7,7a-Tetrahydro-l / Z-isoindole-l,3(2J7)-dione and 1,3- Dihydro-2H-isoindole-l, 3-dione during a process for preparing the salt thereof, the method comprises using sulfonate-based dispersant together with the 3a,4,7,7a- Tetrahydro-17 / -isoindole-l,3(2J7)-dione or l,3-Dihydro-2H-isoindole-l,3-dione.

[0092] The present invention provides a method for reducing the degradation rate of nitrogen compound selected from 3a,4,7,7a-Tetrahydro-l / / -isoindole-l,3(2J7)-dione and 1,3- Dihydro-2H-isoindole-l, 3-dione during a process for preparing the salt thereof, the method comprises the combination of :

[0093] (1) employing the sulfonate-based dispersant in obtaining an aqueous dispersion of solid particulate nitrogen compound, such as in a dispersion of solid particulate 3a,4,7,7a-Tetrahydro-lH-isoindole-l,3(2H)-dione or in a dispersion of solid particulate l,3-Dihydro-2H-isoindole-l, 3-dione and (2) reacting the dispersed solid particles of the nitrogen compound with the aqueous alkaline solution, wherein the solid particulate nitrogen compound is characterized by a particle size distribution such that the D50 value of the dispersed solid particulate 3a,4,7,7a-Tetrahydro-lH- isoindole-l,3(2H)-dione or the dispersed solid particulate l,3-Dihydro-2H-isoindole- 1, 3-dione, is equal or less than 50 microns, such as between 0.1 micron and 50 microns, more commonly between about 1 micron and 50 microns (1 - 50 pm).

[0094] The present invention provides novel reactant mixtures for use in the described novel methods for preparing e.g., water-soluble salts of nitrogen compounds which are either or both of 3a,4,7,7a-Tetrahydro-lH-isoindole-l,3(2H)-dione or of 1,3-Dihydro- 2H-isoindole-l, 3-dione which are themselves useful synthetic reactant intermediates for preparing the phthalimide fungicides such as folpet, captan and Captafol. The novel reactant mixture is an aqueous dispersion of finely divided solid particulates (particles), of nitrogen compounds which are either or both of 3a, 4, 7, 7a- Tetrahydro-lH-isoindole-l,3(2H)-dione or of l,3-Dihydro-2H-isoindole-l, 3-dione and a dispersant, particularly a sulfonate-based dispersant. The finely divided solid particles of 3a,4,7,7a-Tetrahydro-lH-isoindole-l,3(2H)-dione or the finely divided solid particles of l,3-Dihydro-2H-isoindole-l, 3-dione are characterized by a particle size distribution such that the D50 (median) value is 50 micron or less, such as, between about 0.1pm to about 50 pm, or more typically between about 1pm to about 50 pm.

[0095] The dispersant(s) in the novel reactant mixture preferably comprises sulphonate-based dispersant although inventors can foresee other dispersants which will also provide the benefits demonstrated here and clearly mixtures of sulphonate-based and nonsulphonate based dispersants are no deviation from the invention.

[0096] The sulphonate-based dispersant is exemplified by Lignosulphonates such as by the acidic lignosulfonate Reax® 88A. REAX 88A which is a commercially available sodium salt of a chemically modified low molecular weight kraft lignin polymer solubilized by five sulfonate groups.

[0097] In some embodiments, the degradation of the nitrogen compound encountered during the process to prepare the nitrogen compound salt wherein the process includes the sulfonate-based dispersant is at least 5% less than when the same or similar process does not include any sulfonate-based dispersant.

[0098] In some embodiments, the amount of degradation of the nitrogen compound occurring in the process to prepare the nitrogen compound salt is reduced when the process includes employing a dispersion / suspension of the sulfonate-based dispersant and solid particles of nitrogen compound when treated with the aqueous alkaline solution, when the nitrogen compound(s) have a particle size distribution characterized by a D50 value of 50 micron or less (~0.1 - ~50pm), such that the amount of degradation is at least 5% less than a process which does not include sulfonate-based dispersant and the solid particles of nitrogen compound when treated with the aqueous alkaline solution, have a particle size distribution of D50 more than 50 micron. The nitrogen compound(s) are either or both of, 3a,4,7,7a-Tetrahydro-lH-isoindole-l,3(2H)-dione and 1 , 3 -Dihy dro-2H-i soindole- 1 , 3 -di one. An aqueous dispersion comprising, a. a nitrogen compound, b. a dispersant c. water, and optionally d. anti -foam agent, wherein, the nitrogen compound comprises either or both of 3a,4,7,7a-Tetrahydro-lH- isoindole-l,3(2H)-dione and l,3-Dihydro-2H-isoindole-l, 3-dione, and wherein the dispersant is preferably a sulphonate-based, dispersant.

[0099] The present invention also provides the use of sulfonate-based dispersant in process for preparing a salt of nitrogen compound selected from 3a,4,7,7a-Tetrahydro-l H- isoindole-l,3(2J7)-dione and l,3-Dihydro-2H-isoindole-l, 3-dione.

[0100] The present invention also provides the use of sulfonate-based dispersant for dispersing solid particles of one or more nitrogen compounds selected from 3a, 4, 7,7a- Tetrahydro-17 / -isoindole-l,3(2J7)-dione and l,3-Dihydro-2H-isoindole-l, 3-dione in water or aqueous media, optionally further comprising anti -foam agent.

[0101] The present invention provides the combination of (1) use of sulfonate-based dispersant for dispersing finely divided solid particles of a nitrogen compound selected from a group comprising 3a,4,7,7a-Tetrahydro-17 / -isoindole-l,3(2J7)-dione and l,3-Dihydro-2H-isoindole-l, 3-dione in water or aqueous media and (2) solid particles of nitrogen compound when treated with the aqueous alkaline solution, have a particle size distribution characterized by a D50 value of 50 micron or less (~0.1 pm - ~50pm, typically 1 pm - 50pm), for reducing the reaction time required for completion of the reaction preparing the nitrogen compound salt by reaction with alkaline solution, such as Sodium Hydroxide aqueous solution.

[0102] In some embodiments, the reduction in the time required for completion of reaction is reducing by at least 60% of the time that would be needed in similar reactions where no dispersant containing suspension / dispersion was employed.

[0103] In some embodiments, the reduction in time to complete the reaction is exemplified by reducing the time to less than 2 minutes, and often considerably less. In exemplified processes, completion of reaction with minimized degradation is typically achieved in under a minute. In some embodiments the reaction has been completed within seconds, such as between 5 and 30 seconds.

[0104] Nitrogen compound

[0105] The Nitrogen compound is selected from compounds comprising 3a,4,7,7a-Tetrahydro- 177-isoindole-l,3(277)-dione and l,3-Dihydro-2H-isoindole-l, 3-dione or any mixture.

[0106] In some embodiments the 3a,4,7,7a-Tetrahydro-177-isoindole-l,3(277)-dione is cis isomer cis-3a,4,7,7a-Tetrahydro-177-isoindole-l,3(277)-dione

[0107] In some embodiments, the cis isomer cis-3a,4,7,7a-Tetrahydro-177-isoindole-l,3(277)- dione has CAS No. 1469-48-3.

[0108] In some embodiments the 3a,4,7,7a-Tetrahydro-177-isoindole-l,3(277)-dione has CAS No.85-40-5.

[0109] In some embodiments, the l,3-Dihydro-2H-isoindole-l, 3-dione has CAS No. 85-41-6. In some embodiments, the nitrogen compound is cis-3a,4,7,7a-Tetrahydro-177- isoindole-l,3(277)-dione (CAS No. 1469-48-3)

[0110] In some embodiments, the nitrogen compound is l,3-Dihydro-2H-isoindole-l, 3-dione. CAS: 85-41-6.

[0111] Outline of illustrative processes to prepare aqueous dispersions or suspensions of solid particulate Nitrogen Compound(s) including dispersant compound(s). While the exemplified dispersant is sulphonate-based dispersant, inventors envisage other useful dispersants or combinations thereof being able to be used.

[0112] Step 1 preparing dispersion or suspension of Nitrogen Compound with sulfonate- based dispersant.

[0113] In some embodiments, step (1) includes (li) dissolving or otherwise solubilizing a sulfonate-based dispersant in water or aqueous media to obtain a solution or solubilized aqueous mixture of the dispersant, |(lii) adding the nitrogen compound which can be either or both of 3a,4,7,7a-Tetrahydro-177-isoindole-l,3(277)-dione and 1,3-Dihydro- 2H-isoindole-l, 3-dione and |(liii) stirring for at least 10 min to obtain an aqueous dispersion or suspension of the nitrogen compound. In some embodiments, the dynamic viscosity of the dispersion obtained in step (1) is less than 10 Pa*s (pascal second). Note, 0.001 Pa.s = 1 mPa.s = 1 cP (centipoise).

[0114] In some embodiments, the temperature of the solution or aqueous mixture, obtained in step |(li) is between 0 to 10°C.

[0115] In some embodiments, the 3a,4,7,7a-Tetrahydro-l / Z-isoindole-l,3(2J7)-dione is cis isomer cis-3a,4,7,7a-Tetrahydro-U7-isoindole-l,3(2J7)-dione.

[0116] In some embodiments, the nitrogen compound is in its solid typically, particulate, form.

[0117] In some embodiments, the solid form of the nitrogen compound is as flakes with characteristic particle sizes between about 200 micron to about 4 mm (4000 microns).

[0118] In some embodiments the solid form of the nitrogen compound is obtained directly as a finely divided particulate that may be used as is.

[0119] In some embodiments, step (1) is conducted in presence of antifoaming agent

[0120] In some embodiments, step (1) includes a step of adding an antifoaming agent.

[0121] In some embodiments, step (1) is conducted at temperature of 0-15°C.

[0122] In some embodiments, step (1) is conducted at temperature of 0-5°C.

[0123] In some embodiments, the water or aqueous media, used in step (1) is at temperature from 0 to 10 °C.

[0124] In some embodiments, the sulfonate-based dispersant content is 0.05-0.4 w / w% based on the weight of the nitrogen compound in the aqueous dispersion or suspension.

[0125] In some embodiments, the sulfonate-based dispersant is 0.2-0.4 w / w% based on the weight of the nitrogen compound in the aqueous dispersion or suspension.

[0126] In some embodiments, the sulfonate-based dispersant is 0.05-0.4 w / w% based on the weight of the Nitrogen Compound, cis-3a,4,7,7a-Tetrahydro-lH-isoindole-l,3(2H)- dione in the aqueous dispersion or suspension.

[0127] In some embodiments, the sulfonate-based dispersant is 0.2-0.4 w / w% based on the weight of the Nitrogen Compound, cis-3a,4,7,7a-Tetrahydro-lH-isoindole-l,3(2H)- dione in the aqueous dispersion or suspension. In some embodiments, the sulfonate-based dispersant is 0.05-0.4 w / w% based on the weight of the Nitrogen Compound, l,3-Dihydro-2H-isoindole-l, 3-dione in the aqueous dispersion or suspension.

[0128] In some embodiments, the sulfonate-based dispersant is 0.2-0.4 w / w% based on the weight of the Nitrogen Compound, l,3-Dihydro-2H-isoindole-l, 3-dione in the aqueous dispersion or suspension.

[0129] In some embodiments, the weight ratio between the water to the nitrogen compound which is cis-3a,4,7,7a-Tetrahydro-lH-isoindole-l,3(2H)-dione in step (1) is 3.5 :1 to 4: 1 in the aqueous dispersion or suspension.

[0130] In some embodiments, the weight ratio between the water to the nitrogen compound which is l,3-Dihydro-2H-isoindole-l, 3-dione in step (1) is 4.5: 1 to 5: 1 in the aqueous dispersion or suspension .

[0131] Step 2 Bringing the dispersion or suspension of Nitrogen Compound into contact with, and reaction with aqueous alkaline solution.

[0132] In some embodiments, concentration of the aqueous alkaline solution is 15% -28%.

[0133] In some embodiments, the aqueous alkaline solution is an aqueous solution of an alkali metal hydroxide or a metal salt of carbonate, wherein the concentration of the aqueous alkali metal hydroxide or metal salt of carbonate in the solution is between about 15% to about 28% ( 13 - 3 1%).

[0134] In some embodiments, reacting the dispersion or suspension of step (1) with aqueous alkaline solution, wherein the equivalents of the base to nitrogen compound is about 1.05: 1 to about 1.4: 1. In some embodiments

[0135] In some embodiments, reacting the dispersion or suspension of step (1) with aqueous alkaline solution, wherein the equivalents of the base to nitrogen compound is only about 1.05: 1. The base used in the aqueous alkaline solution is often Sodium Hydroxide.

[0136] In some embodiments, reacting the dispersion or suspension of step (1) with aqueous alkaline solution, wherein the equivalents of the base to nitrogen compound is only about 1.05: 1 while the yield is about 90% or more after a reaction time that does not exceed 2 minutes, and often after considerably less time. In some embodiments, the aqueous alkaline solution is a solution comprising metal salt of carbonate.

[0137] In some embodiments, aqueous alkaline solution is a solution comprising a metal salt of hydroxide.

[0138] In some embodiments, molar ratio between the nitrogen compound and the carbonate is between about 1 : 1 to 1 : 1.4.

[0139] In some embodiments, molar ratio between the nitrogen compound and the hydroxide is between about 1 : 1 to 1 : 1.4.

[0140] In some embodiments, the alkali hydroxide is sodium hydroxide.

[0141] In some embodiments, step (2) reacting the dispersed solid particles of the nitrogen compound with the aqueous alkaline solution, is conducted in presence of antifoaming agent.

[0142] In some embodiments, step (2) reacting (treating) the dispersed solid particles of the nitrogen compound with the aqueous alkaline solution, is conducted at temperature of 0-15°C.

[0143] In some embodiments, step (2) reacting the dispersed solid particles of the nitrogen compound with the aqueous alkaline solution, is conducted at temperature of 0-5°C.

[0144] In some embodiments, the solid particles of nitrogen compound at the time that it is when treated or reacted, with the aqueous alkaline solution is characterized by a particle size distribution such that the D50 value of the solid particles is equal or less than 50 microns, such as between 0.1 micron and 50 microns, more commonly between about 1 micron and 50 microns (1 pm - 50 pm)..

[0145] In some embodiments, the particle size distribution of the nitrogen Compound when it is treated or reacted with the aqueous alkaline solution is achieved by milling such as a media mill (ball mill), or other size reduction technique to achieve the preferred fine particle size distribution, in some embodiments the equipment to achieve the particle size reduction of the nitrogen compound is in-line, allowing one or multiple passes through the equipment and passage through to the next stage. In some embodiments the reaction between the fine particulate and the aqueous alkaline solution occurs within the same equipment that reduces the particle size distribution of the imide particles.

[0146] In some embodiments the processes to form the novel reactant mixture (suspension / dispersion), reduce modulate the particle size of imide particles, react with aqueous alkaline solution to obtain imide salt dissolved in aqueous media and then react with mercapto compound to produce the phthalimide fungicidal compound is a continuous process. In some of these embodiments the components of the novel reactant mixture (suspension / dispersion), nitrogen compound, dispersant, and water (or aqueous media) are fed into the process equipment in parallel with introducing the aqueous alkaline solution (e.g., NaOH solution). The equipment mixes the components with the alkaline solution (e.g., NaOH solution) at high shear while simultaneously reducing the particle size of the imide particle such as 3a, 4, 7,7a- Tetrahydro-l / / -isoindole-l,3(2J7)-dione or l,3-Dihydro-2H-isoindole-l, 3-dione and transfers the obtained aqueous solution of imide salt to the reaction with the mercapto compound to form the phthalimide salt. In some preferred embodiments the equipment comprises high shear pump equipment and the residence time within the high shear pump is less than 2 minutes and preferably a minute or less while achieving complete reaction and reduced degradation products.

[0147] In some preferred embodiments the process is a batch process and in some embodiments the process is a continuous process, in notable embodiments, the process equipment equipment comprises high shear pump equipment or in-line media milling equipment and the residence time within the equipment is optimally less than 2 minutes and preferably a minute or less while achieving complete reaction and reduced degradation products. In preferred embodiments passage through high shear pump equipment or mill is achieved by multiple passes through the equipment, or by arranging multiple high shear pumps in series.

[0148] Variations in equipment and arrangement thereof will not depart from the invention and are predicted. So long as the basic principles of employing the novel reactant mixture of imide particle and dispersant sulphonate-based dispersant dispersed in aqueous media and reacting with aqueous alkaline solution is achieved. Optimizations of the process, the equipment and the reaction conditions are well within the skills of the persons or team of skill in these arts.

[0149] In many embodiments the combination of imide solid particles, dispersant (e.g., lignosulphonate), water, base (such as NaOH or metal carbonate), beneficially further comprises antifoam agent such as silicone oil-based compound or mixture either introduced separately or as part of the novel reactant mixture or alkaline solution.

[0150] In some embodiments, the particle size distribution of the nitrogen Compound when it is treated or reacted with the aqueous alkaline solution is the same as obtained prior to forming the dispersion or suspension at the preferred fine particle size distribution achieved through manipulation of the process by which it is prepared. The processes by which synthesis of the Nitrogen Compound can result in finely divided particulates suitable for immediate use here is not the central focus of this work.

[0151] In some embodiments, milling of the particles is conducted in parallel, or concomitantly to the addition of the aqueous alkaline solution or otherwise bringing the two into contact.

[0152] In some embodiments, the space within which the aqueous alkaline solution is contacted with the aqueous dispersion or suspension of the nitrogen compound is equipped such that mixing of the liquids and size reduction of the particulate Nitrogen Compound occurs at the same time or in parallel.

[0153] In some embodiments, milling or size reduction or modulation of the nitrogen Compound particles occurs prior to the adding of the aqueous alkaline solution, or bringing them otherwise into contact.

[0154] The methods by which particles are formed with defined particle size distributions are not a central feature of the invention although ordinarily skilled practitioners will be well aware of the many techniques and may find some more useful.

[0155] In some embodiments, step (2), bringing into contact the dispersed solid particles of the nitrogen compound with the aqueous alkaline solution (reacting or treating) is conducted in high shear equipment. In some embodiments, step (2), bringing into contact the dispersed solid particles of the nitrogen compound with the aqueous alkaline solution (reacting or treating) is conducted in high shear pump equipment or within similar equipment that both reduces particle sizes and mixes.

[0156] In some embodiments, step (2) of bringing into contact the dispersed solid particles of the nitrogen compound with the aqueous alkaline solution to achieve reaction, is conducted at least 2 times (2 passes), wherein the total time for the reaction with the aqueous alkaline solution is up to Imin.

[0157] In some embodiments, less than a minute is required for the reaction to achieve completion because of the use of the inventive dispersion of Nitrogen Compound and dispersant. This is particularly the case when the processing equipment and process flow is optimized as described. The reduced processing time also results in reduced degradation of the reactants compared with previously encountered similar processes.

[0158] In previously reported processes to produce water-soluble imide sodium salts, the amount of NaOH required for the reaction with particles of 3a,4,7,7a-Tetrahydro-lH- isoindole-l,3(2H)-dione or l,3-Dihydro-2H-isoindole-l, 3-dione is generally in significant excess ostensibly to maximize reaction completeness.

[0159] In some embodiments of the inventive reactant intermediate mixture a.k.a. a dispersed reactant mixture and the inventive reaction process, the increased efficiency and completeness of the reaction allows the molar excess of the NaOH in the alkaline aqueous solution can be reduced. In some embodiments the molar ratio between nitrogen compound and NaOH can be particles selected 3a,4,7,7a-Tetrahydro-lH- isoindole-l,3(2H)-dione or l,3-Dihydro-2H-isoindole-l, 3-dione is generally in significant excess ostensibly to maximize reaction completeness.

[0160] In some embodiments, the bringing into contact, the dispersion of the Nitrogen Compound with the aqueous alkaline solution (treatment or reaction), is by using 2 Inline High Shear pumps in series.

[0161] In some embodiments, multiple passes through High shear pumps each with low residence time can be beneficial. Similarly, In some embodiments, passes through multiple in line High shear pumps each with low residence time can be beneficial.

[0162] T1 Two (or more), passes are often beneficially achieved whereby the particle size reduction and reaction efficiency are maximized in a shortened residence time and often a concomitant reduction in degradation of reactant.

[0163] In some embodiments, the bringing into contact, the dispersion of the Nitrogen Compound with the aqueous alkaline solution (treatment or reaction), is a continuous process by using 2 (or more), In-line High Shear pumps in series and feeding the dispersed reactant dispersion and aqueous alkaline solution in parallel into the processing spaces can be beneficial to efficacy yield and reduction in degradation.

[0164] In some embodiments the process is a batch process. Sometimes the choice of Batch based process is an equipment-based or a policy-based decision.

[0165] In some embodiments the reaction (treatment) of the dispersed particles of nitrogen compound with aqueous alkaline solution the pH of the reaction mixture is constantly monitored, and the pH is maintained at between 9 and about 11 (e.g., 9 - 10.5), by the addition of portions of additional amounts of NaOH over the period of reaction. Clearly the extremely reduced reaction times achieved can allow for limiting this addition in some embodiments.

[0166] In some embodiments, the time for conducting step (2) treatment is less than 1 minute, and this is sufficient for the reaction to occur facilitated by the invention.

[0167] In some embodiments, the time required for conducting step (2) is less than 30 sec

[0168] In some embodiments, the time required for conducting step (2) less than 20 sec

[0169] In some embodiments, the time required for conducting step (2) is 15 sec.

[0170] In some embodiments, the time required for conducting step (2) is 10 sec

[0171] In some embodiments, the time required for conducting step (2) is 5 sec.

[0172] As will be readily appreciated by skilled artisans, the reduction in the time required (seconds or less), to complete the reaction between alkaline aqueous solutions and dispersions of finely divided particles 3a,4,7,7a-Tetrahydro-lH-isoindole-l,3(2H)- dione or of l,3-Dihydro-2H-isoindole-l, 3-dione combined with sulphonate-based dispersant, brings further processing equipment and techniques into the realm of being practical. Such processes for bringing the two aqueous liquids into contact could be envisioned such as those exemplified by contact through impinging streams of liquid or even aerosols.

[0173] The described improved reactants and processes and materials processing improvements herein described allow for continuous as well as batch-based processes as described herein.

[0174] In some embodiments, the aqueous dispersion, or suspension of Nitrogen Compound fine solid particles with sulphonate-based dispersants will also include antifoaming agent. In some embodiments, the antifoaming agent is a silicon oil-based compound, mixture or composition.

[0175] In some embodiments, the silicon based antifoam agent is poly dimethyl siloxane oil such as found in Rhodorsil antifoam 426 or SILCOLAPSE® 426 which is a non-ionic aqueous emulsion based on poly dimethyl siloxane oil containing 30% active matter content available from Elkem (Bluestar Silicones).

[0176] In some process embodiments, In-line high shear pump is employed such that a continuous milling of the water-based dispersion of the Nitrogen Compound and dispersant obtained in step (1) in parallel with continuous dosing of cold aqueous alkaline solution to dispersion of step (1) which at temperature of 0 -5°C can occur to efficiently bring the two aqueous liquids into efficient contact.

[0177] In some embodiments, cold aqueous alkaline solution is at temperature of (-5) °C.

[0178] Step 3, to convert the salt of the of 3a,4,7.,7a-Tetrahvdro-lH-isoindole-l.,3(2H)- dione or salt of l,3-Dihydro-2H-isoindole-l, 3-dione into phthalimide fungicide by reacting the salt with perchloromethyl mercaptan or pentachloroethyl mercaptan (PCEM).

[0179] In some embodiments, step 3 as referred to above can be conducted as described for example in US2553770 and US2553771

[0180] Step 4, isolating the phthalimide based fungicide.

[0181] In some embodiments, the step (4) isolation includes filtration of the solid.

[0182] In some embodiments, the step (4) isolation includes washing with water.

[0183] In some embodiments, the step (4) isolation includes drying. In some embodiments, the step (4) isolation includes filtration, washing and drying.

[0184] In some embodiments, step (4) includes purification such as described in WO2023 / 119286.

[0185] In some embodiments, the step (4) isolation includes removing remnants of the sulphonate-based dispersant and antifoam agent that might still remain associated with the phthalimide based fungicide from the initial stages of the processes.

[0186] In some embodiments the novel process of the invention include the following illustrative embodiments.

[0187] Dispersion / Suspension of 3a,4,7,7a-Tetrahvdro-lJ / -isoindole-l,3(2Zf)-dione particles with Lignosulfonate as sulphonate-based dispersant. Imide Slurry, solid flakes (200pm - 4mm) of 3a,4,7,7a-Tetrahydro-17 / -isoindole-l,3(2J7)-dione and sulphonate- based dispersant such as lignosulphonate, are mixed with water (or aqueous media), at temperatures below 10°C and dispersed to form a dispersion / suspension optionally together with antifoam agent. The dispersion / suspension is processed to reduce the particle size distribution until the particle size distribution of the dispersed solid particles is characterized by a D50 value below 50 microns to obtain the Imide Slurry.

[0188] In the alternative pre-milled 3a,4,7,7a-Tetrahydro-17 / -isoindole-l,3(2J7)-dione is combined with sulphonate-based dispersant such as lignosulphonate, mixed with water (or aqueous media), at temperatures below 10°C and dispersed to form a dispersion / suspension optionally together with antifoam agent.

[0189] Dispersion / Suspension of L3-Dihydro-2H-isoindole-L3-dione (Phthalimide) particles with Lignosulfonate as sulphonate-based dispersant. Imide Slurry, solid flakes (200pm - 4mm) of 3a,4,7,7a-Tetrahydro-17 / -isoindole-l,3(2J7)-dione and sulphonate- based dispersant such as lignosulphonate, are mixed with water (or aqueous media), at temperatures below 10°C and dispersed to form a dispersion / suspension optionally together with antifoam agent. The dispersion / suspension is processed to reduce the particle size distribution until the particle size distribution of the dispersed solid particles is characterized by a D50 value below 50 microns to obtain the Imide Slurry. In the alternative pre-milled l,3-Dihydro-2H-isoindole-l,3-dione (Phthalimide) is combined with sulphonate-based dispersant such as lignosulphonate, mixed with water (or aqueous media), at temperatures below 10°C and dispersed to form a dispersion / suspension optionally together with antifoam agent.

[0190] Preparing Dispersion / Suspension of 3a,4,7,7a-Tetrahydro-U7-isoindole-l,3(2J7)-dione with Lignosulfonate as sulphonate-based dispersant, reaction with NaOH aqueous solution and then further reacted with PCMM. Solid 3a,4,7,7a-Tetrahydro-U7- isoindole-l,3(2J7)-dione, lignosulphonate Sodium Salt (Reax 88A), are mixed with water, (or aqueous media), at temperatures below 10°C. A solution containing NaOH in water, is added while the temperature is maintained at temperatures below 10°C. The resultant mixture remains under vigorous stirring until full dissolution to provide a 3a,4,7,7a-Tetrahydro-lH-isoindole-l,3(2H)-dione sodium salt solution (Imide Salt Solution). PCMM and the 3a,4,7,7a-Tetrahydro-U / -isoindole-l,3(2J7)-dione sodium salt solution obtained are added in parallel into a stirred reactor for the time required to the reaction to be complete which period of time will often depend on the equipment and its arrangement, while the pH is maintained at alkaline pH above pH 8 such as a pH of 9-12, optionally by adding further NaOH. The temperature is maintained at temperatures below 10°C. After completion of the reaction, the reaction mixture is filtered, and the obtained solid is preferably washed with water, and dried. In some embodiments the stirred reactor is one or more high shear pumps.

[0191] Process, Preparing Dispersion / Suspension of L3-Dihydro-2H-isoindole-L3-dione (Phthalimide), with Lignosulfonate as sulphonate-based dispersant reaction with NaOH aqueous solution and then further reacting with PCMM, Solid flakes of 1,3- Dihydro-2H-isoindole-l, 3-dione (Phthalimide), and lignosulphonate sodium such as Reax 88A, are mixed with water, at temperatures below 10°C. A solution containing NaOH in water, is added while the temperature is maintained at temperatures below 10°C. The resultant mixture is maintained under vigorous stirring until full dissolution to provide a l,3-Dihydro-2H-isoindole-l, 3-dione sodium salt solution (Imide Salt Solution). PCMM and the l,3-Dihydro-2H-isoindole-l,3-dione sodium salt solution that is obtained in the previous step are added in parallel into a stirred reactor for the time required to the reaction to be complete which period of time will often depend on the equipment and its arrangement, while the pH is maintained at alkaline pH above pH 8 such as a pH of 9-12. The temperature is maintained at below 10°C.

[0192] After completion of the reaction, the reaction mixture is preferably filtered, and the obtained solid is preferably washed with water.

[0193] Preparing and Reacting 3a,4,7,7a-Tetrahydro-U / -isoindole-L3(2J7)-dione and Lignosulfonate (sulphonate-based dispersant) dispersion / suspension with aqueous NaOH in In-line High shear pump and then further reacted with PCMM to provide phthalimide fungicide. Solid 3 a,4,7,7a-T etrahydro- UT-isoindole- 1 ,3 (27 / )-di one and Reax 88A, are mixed with water, at below 10°C. 3a,4,7,7a-Tetrahydro-U / -isoindole- 1 ,3(27 / )-dione dispersion in water and a solution containing NaOH in water (or aqueous media), is pumped in parallel to In-line High shear pump with total residence time 0.5-1 minute. The temperature maintained at below 10°C. The resultant 3a,4,7,7a-Tetrahydro-U / -isoindole-l,3(2J7)-dione sodium salt (Imide Salt Solution), and PCMM are added in parallel into stirred reactor for 15 minutes, while the pH is maintained at alkaline pH above pH 8 such as a pH of 9-12. The temperature is maintained at below 10°C. After completion of the reaction, the reaction mixture is preferably filtered, washed with water, and dried.

[0194] Pumping to or through one or more In-line High shear pumps with residence time 0.5- 1 minute, results in a fine solid particle size distribution such as by a D50 value of 50 microns and below.

[0195] Preparing and Reacting L3-Dihydro-2H-isoindole-L3-dione (Phthalimide) dispersion / suspension with aqueous NaOH in In-line High shear pump and then further reacting with PCMM to provide phthalimide fungicide. Solid flakes of 1,3- Dihydro-2H-isoindole-l, 3-dione (Phthalimide) and Reax 88A, are mixed with water, at below 10°C. The obtained l,3-Dihydro-2H-isoindole-l, 3-dione (Phthalimide) dispersion / suspension in water (Imide slurry), and a solution containing NaOH in about water, are pumped in parallel to In-line High shear pump with residence time 0.5-1 minute and the temperature is maintained at below 10°C. This reduces the solid particle size of the phthalimide to a fine particle size distribution such as characterized by a D50 value of 50 microns and below and reacts with NaOH to efficiently produce the l,3-Dihydro-2H-isoindole-l, 3-dione sodium salt solution (water-soluble Imide Salt solution). The l,3-Dihydro-2H-isoindole-l, 3-dione sodium salt (water-soluble Imide Salt solution), and PCMM are added in parallel into a reactor equipped with stirring means until the reaction is complete, while the pH is maintained at alkaline pH above pH 8 such as a pH of 9-12. The temperature is maintained at below 10°C. After completion of the reaction, the reaction mixture is typically filtered, washed with water, and dried.

[0196] Solid 3a,4,7,7a-Tetrahydro-U / -isoindole-l,3(2J7)-dione is mixed with water, at below 10°C. Solution containing NaOH in water, is added while temperature maintained at below 10°C. Mixture remains under vigorous stirring until full dissolution.

[0197] PCMM and the 3a,4,7,7a-Tetrahydro-lH-isoindole-l,3(2H)-dione sodium salt solution are added in parallel into stirred reactor for until reaction is completed, while the pH is maintained between at alkaline pH above pH 8 such as a pH of 9-12. The temperature is maintained below 10°C. After completion of the reaction, the reaction mixture is typically filtered, washed with water, and dried. l,3-Dihydro-2H-isoindole-l, 3-dione (Phthalimide) are mixed with water below 10°C. A solution containing NaOH in water, is added while temperature is maintained at below 10°C. Mixture is maintained under vigorous stirring until full dissolution to obtain l,3-Dihydro-2H-isoindole-l, 3-dione Sodium salt solution.

[0198] PCMM (1 mol) and the obtained l,3-Dihydro-2H-isoindole-l, 3-dione sodium salt solution are added in parallel into a stirred reactor until completion, while the pH is maintained at alkaline pH above pH 8 such as a pH of 9-12. The temperature is maintained at 0-5°C. After completion of the reaction, the reaction mixture is typically filtered, and washed with water.

[0199] While the inventive processes are typically part of an entire process eventually resulting in isolated, dried, purified, and packaged phthalimide fungicidal compounds such as folpet, captan or captafol, the invention is not dependent on any of the steps such as, reaction with mercapto-compound (PCMM or PCEM), isolation, drying, purification or packaging. Processes employing a dispersion of imide particles with sulphonate dispersant (Imide slurry), and contact with an alkaline aqueous solution is the central feature, while adding steps, processes, equipment, or any additional ingredients and resulting in anything more than an aqueous solution of imide salt, in no way departs from the invention. Such additional processes conditions, work-up, packaging etc., should be considered, enhancements, optimizations, or preferred embodiments of the invention. Even a totally unfiltered, or undried, impure unpackaged phthalimide fungicidal compound can be considered to be a product of the invention if the synthetic process to produce it employs the inventive Imide slurry (novel reactant mixture), comprising the dispersant and particulate imide. The invention is not limited by the quality of the product produced.

[0200] Sulfonate-Based Dispersant

[0201] In some embodiments, the sulfonate-based dispersant comprises poly sulfonate structure.

[0202] In some embodiments, the sulfonate-based dispersant is a chemically modified lignin polymer solubilized by sulfonate groups such as, lignosulfonate

[0203] In some embodiments, the dispersant is Alkylnaphthalene sulfonate (ANS) condensate blend.

[0204] In some embodiments, the dispersant is Polyfon H. POLYFON® H is a low molecular weight kraft lignosulfonate with a low degree of sulfonation available from Ingevity 4920 O 'Hear Avenue, Suite 400, North Charleston, S.C. 29405 USA

[0205] In some embodiments, the dispersant is Reax 100M. Reax 100M is a highly sulfonated kraft lignin available from Ingevity.

[0206] In some embodiments, the dispersant is Reax 88A.

[0207] In some embodiments, the dispersant is Borresperse Na which contains greater or equal to 93% Sodium Lignosulphonate CAS No. 8061-51-6 in water available from Borregaard AS.

[0208] In some embodiments, the Alkylnaphthalene sulfonate (ANS) condensate blend is Morwet D-450. Morwet® D-450 is a blend of sodium salt of naphthalene sulfonate condensate (NSC) and wetting agent (particularly a sodium salt of alkyl naphthalene sulfonate condensate with a block copolymer, available from (Akzo Nobel / Witco ) Nouryon Haaksbergweg 88, De Oliphant Building, Floor 14 and 15 1101 BZ, Amsterdam, The Netherlands.

[0209] Lignosulfonate, an exemplary sulphonate-based dispersant in the invention In some embodiments, the lignosulfonate is calcium lignosulfonate. In some embodiments, the lignosulfonate is sodium lignosulfonate.

[0210] In some embodiments the molecular weight of lignosulfonate is less than 20,000 Da. In some embodiments, the degree of sulfonation of lignosulfonate at least 0.7. Lignosulfonate (also termed lignosulphonate, lignosulfate, lignin sulfonate, ligninsulfonate, ligninsulfonic acid, lignosulfonic acid, lignosulfuric acid, or LST 7) is a water-soluble anionic polymer which is, for example, formed as a by-product in the sulphite pulping process. Lignosulfonates generally have a wide molecular weight distribution, typically in the range of about 500-5000 Da.

[0211] In some embodiments, the lignosulfonate is miscible in water. Lignosulfonates may comprise different metal or ammonium ions as counter cations of the sulfonate groups such as, for example, copper, zinc, calcium, sodium, potassium, magnesium and aluminium. Suitable examples of lignosulfonates comprise sodium lignosulfonate (e.g. sold as BORRESPERSE NA®, Borregaard LignoTech Ltd, Germany), calcium lignosulfonate (e.g. sold as BORRESPERSE CA®, Borregaard LignoTech Ltd, Germany), ammonium lignosulfonate, potassium lignosulfonate, modified lignosulfonate, derivatives of lignosulfonate, or mixtures thereof. Modified lignosulfonates, and derivatives of lignosulfonates are described in U.S. Patent Nos.: 3639263, 3923532, 4006779, 4017475, 4019995, 4069217, 4088640, 4133385, 4181652, 4186242, 4196777, 4219471, 4236579, 4249606, 4250088, 4267886, 4269270, 4293342 4336189, 4344487, 4594168, 4666522, 4786438, 5032164, 5075402, 5286412, 5401718, 5446133, 5981433, 6420602, and 7238645, which are incorporated herein by reference.

[0212] In some embodiments, lignosulfonate is copper-, zinc-, calcium-, sodium-, potassium- , ammonium-, magnesium- and / or aluminium- lignosulfonate, In some embodiments, calcium, sodium, potassium or ammonium lignosulfonate, In some embodiments, the lignosulfonate is sodium lignosulfonate.

[0213] In some embodiment the lignosulfonate is Vanisperse CB available from Borregaard, P.O Box 162, N-1701 Sarpsborg, Norway

[0214] In some embodiments, the lignosulfonate is basic.

[0215] In some embodiments, the basic lignosulfonate is Reax 88B. Reax 88B is a highly sulfonation and low molecular weight kraft lignin polymer with a basic pH available from (Ingevity) MeadWestvaco Corporation PO Box 118005 Charleston, SC 29423- 8005. In some embodiments, the lignosulfonate is acidic.

[0216] In some embodiments, the acidic lignosulfonate is Reax 88A. In addition, please note, when lists are provided in this disclosure, the list is to be considered as a disclosure of each individual member in the list, independently of any of the others, typically organized in a list for convenience.

[0217] This invention will be better understood by reference to the Experimental Details which follow, but those skilled in the art will readily appreciate that the specific experiments detailed are only illustrative of the invention as described more fully in the claims which follow thereafter.

[0218] The invention is illustrated by the following examples without limiting it thereby.

[0219] Example A, Dispersion / Suspension of 3aA7,7a-Tetrahydro-17 / -isoindole-L3(2Zf)- dione particles with Lignosulfonate as sulphonate-based dispersant - Imide Slurry,

[0220] About 1 mol (about 151g), of solid flakes (200pm - 4mm) of 3a,4,7,7a-Tetrahydro- IT / -isoindole- l ,3(27 / )-dione and about 0.6 gr of Reax 88A, are mixed with about 600 cc. of water, at 0-5°C and dispersed to form a dispersion / suspension.

[0221] The dispersion / suspension is processed to reduce the particle size distribution until the particle size distribution of the dispersed solid particles is characterized by a D50 value below 50 microns to obtain the Imide Slurry.

[0222] Example B, Dispersion / Suspension of lH-Isoindole-L3(2H)-dione (Phthalimide) particles with Lignosulfonate as sulphonate-based dispersant - Imide Slurry,

[0223] About 1 mol (about 147g), of solid flakes (200pm - 4mm) of 1,3-Dihydro-2H- isoindole-1, 3-dione (Phthalimide), and about 0.6 gr of Reax 88A, are mixed with about 735cc. of water, at 0-5°C and dispersed to form a dispersion / suspension.

[0224] The dispersion / suspension is processed to reduce the particle size distribution until the particle size distribution of the dispersed solid particles is characterized by a D50 value below 50 microns to obtain the Imide Slurry.

[0225] Example la. Process, Preparing Dispersion / Suspension of 3aA7,7a-Tetrahydro-lJ / - isoindole-L3(2Zf)-dione with Lignosulfonate as sulphonate-based dispersant reaction with NaOH aqueous solution and then further reacted with PCMM,

[0226] 151 gr (1 mol) of solid 3a,4,7,7a-Tetrahydro-U / -isoindole-l,3(2J7)-dione and 0.6 gr of Reax 88A, were mixed with 600 cc. of water, at 0-5°C. A solution containing 42 grams of NaOH (1.05 mol) in 258 grams of water, was added while the temperature was maintained at 0-5°C. The resultant mixture remained under vigorous stirring until full dissolution (1-5 minutes) to provide a 3a,4,7,7a-Tetrahydro-lH-isoindole-l,3(2H)- dione sodium salt solution (Imide Salt Solution).

[0227] 186 gr (110 mL) of PCMM (1 mol) and the 3a,4,7,7a-Tetrahydro-U7-isoindole- l,3(2J7)-dione sodium salt solution obtained were added in parallel into a stirred reactor for 15 minutes, while the pH was maintained between pH 9 and pH 10.5. The temperature was maintained at 0-5°C. After completion of the reaction, the reaction mixture was filtered, and the obtained solid was washed with water, and dried.

[0228] Yield 87%.

[0229] Example lb. Process, Preparing Dispersion / Suspension of l,3-Dihydro-2H-isoindole- 1, 3-dione (Phthalimide), with Lignosulfonate as sulphonate-based dispersant reaction with NaOH aqueous solution and then further reacting with PCMM,

[0230] About 1 mol (about 147g), of solid flakes (200pm - 4mm) of 1,3-Dihydro-2H- isoindole-1, 3-dione (Phthalimide), and about 0.6 gr of Reax 88A, are mixed with about 735 cc. of water, at 0-5°C. A solution containing about 42 grams of NaOH (1.05 mol) in 258 grams of water, is added while the temperature is maintained at 0-5°C. The resultant mixture is maintained under vigorous stirring until full dissolution to provide a l,3-Dihydro-2H-isoindole-l, 3-dione sodium salt solution (Imide Salt Solution).

[0231] 186 gr (110 mL) of PCMM (1 mol) and the l,3-Dihydro-2H-isoindole-l, 3-dione sodium salt solution that is obtained in the previous step are added in parallel into a stirred reactor for about 15 minutes, while the pH is maintained between pH 10 and pH 11.5. The temperature is maintained at 0-5°C.

[0232] After completion of the reaction, the reaction mixture filtered, and the obtained solid washed with water, and dried. Yield 80%.

[0233] Example 2a: Preparing and Reacting 3a,4,7,7a-Tetrahydro-U / -isoindole-l,3(2Zf)- dione and Lignosulfonate (sulphonate-based dispersant) dispersion / suspension with aqueous NaOH in In-line High shear pump and then further reacted with PCMM to provide phthalimide fungicide. 151 gr (1 mol) of solid 3a,4,7,7a-Tetrahydro-U / -isoindole-l,3(2J7)-dione and 0.6 gr of Reax 88A, were mixed with 453cc. of water, at 0-5°C. 3a,4,7,7a-Tetrahydro-UT- isoindole-l,3(2J7)-dione dispersion in water and a solution containing 42 grams of NaOH (1.05 mol) in 258 grams of water, was pumped in parallel to In-line High shear pump with residence time 0.5-1 minute. The temperature maintained at 0-5°C. The resultant 3a,4,7,7a-Tetrahydro-U / -isoindole-l,3(2J7)-dione sodium salt (Imide Salt Solution), and 186 gr (110 mL) of PCMM (1 mol) were added in parallel into stirred reactor for 15 minutes, while the pH was maintained between pH 9 and pH 10.5. The temperature was maintained at 0-5°C. After completion of the reaction, the reaction mixture was filtered, washed with water, and dried. Yield 92%.

[0234] Pumping to In-line High shear pump with residence time 0.5-1 minute, results in solid particle size distribution characterized by a D50 value of 50 microns and below.

[0235] Example 2b: Preparing and Reacting L3-Dihydro-2H-isoindole-L3-dione (Phthalimide) dispersion / suspension with aqueous NaOH in In-line High shear pump and then further reacting with PCMM to provide phthalimide fungicide.

[0236] About 1 mol (about 147g), of solid flakes (200pm - 4mm) of 1,3-Dihydro-2H- isoindole-1, 3-dione (Phthalimide) and about 0.6 gr of Reax 88A, are mixed with about 735cc. of water, at 0-5°C.

[0237] The obtained l,3-Dihydro-2H-isoindole-l, 3-dione (Phthalimide) dispersion / suspension in water (Imide slurry), and a solution containing about 42 grams of NaOH (1.05 mol) in about 258 grams of water, are pumped in parallel to In-line High shear pump with residence time 0.5-1 minute and the temperature is maintained at 0- 5°C. This reduces the solid particle size of the phthalimide to a particle size distribution characterized by a D50 value of 50 microns and below and reacts with NaOH to efficiently produce the l,3-Dihydro-2H-isoindole-l, 3-dione sodium salt solution (water-soluble Imide Salt solution).

[0238] The l,3-Dihydro-2H-isoindole-l, 3-dione sodium salt (water-soluble Imide Salt solution), and 186 gr (110 mL) of PCMM (1 mol) are added in parallel into a reactor equipped with stirring means for 15 minutes, while the pH is maintained between pH 9 and pH 11. The temperature is maintained at 0-5°C. After completion of the reaction, the reaction mixture filtered, washed with water, dried. Yield 88% Example 3a

[0239] 151 gr (1 mol) of solid 3a,4,7,7a-Tetrahydro- l / / -isoindole- l ,3(2 / / )-dione was mixed with 600 cc. of water, at 0-5°C. Solution containing 42 grams of NaOH (1.05 mol) in 258 grams of water, was added while temperature maintained at 0-5°C. Mixture remained under vigorous stirring until full dissolution (5-10 minutes)

[0240] 186 gr (110 mL) of PCMM (1 mol) and the 3a,4,7,7a-Tetrahydro-U7-isoindole- l,3(2J7)-dione sodium salt solution were added in parallel into stirred reactor for 15 minutes, while the pH is maintained between pH 9 and pH 10.5. The temperature was maintained at 0-5°C. After completion of the reaction, the reaction mixture was filtered, washed with water, and dried. Yield 85%.

[0241] Example 3b

[0242] About 1 mol (about 147g), of l,3-Dihydro-2H-isoindole-l,3-dione (Phthalimide) are mixed with about 735cc. of water at 0-5°C.

[0243] A solution containing about 42 grams of NaOH (1.05 mol) in about 258 grams of water, is added while temperature is maintained at 0-5°C. Mixture is maintained under vigorous stirring until full dissolution (5-10 minutes) to obtain 1,3-Dihydro-2H- isoindole-1, 3-dione Sodium salt solution.

[0244] About 186 gr (110 mL) of PCMM (1 mol) and the obtained 1,3-Dihydro-2H- isoindole-1, 3-dione sodium salt solution are added in parallel into a stirred reactor for 15 minutes, while the pH is maintained between pH 9 and pH 11. The temperature is maintained at 0-5°C. After completion of the reaction, the reaction mixture filtered, washed with water, dried. Yield 78%.

[0245] Statements, (features, aspects, etc.) and embodiments of the compositions, methods, equipments, and uses described herein are set herein below. Each of the statements and embodiments so defined may be combined with any other statement and / or embodiments unless clearly indicated to the contrary. In particular, any feature indicated as being preferred or advantageous may be combined with any other feature or features or statements indicated as being preferred or advantageous. Hereto, the application in particular relates to any one or any combination of one or more of the below numbered statements, aspects, embodiments etc., with any other statement and / or embodiment. The ensuing statements provide additional illustration of certain aspects and embodiments that have been disclosed in accordance with the present invention:

[0246] Statements

[0247] 1. A process for producing phthalimide based fungicide employing a dispersed reactant mixture comprising, a. preparing a dispersed reactant mixture, b. reacting the obtained reactant mixture of step a. with aqueous alkaline solution to obtain a salt, preferably in aqueous solution, c. reacting the resulting salt from step b. with mercapto-based compound selected from perchloromethyl mercaptan (PCMM) and pentachloro ethyl mercaptan (PCEM) to obtain phthalimide based fungicide, and optionally, d. isolation and purification of the phthalimide based fungicide obtained in step c. , wherein the dispersed reactant mixture is a water-based dispersion or aqueous suspension comprising solid particles of a nitrogen compound selected from 3 a, 4, 7,7a-T etrahy dro- 17 / -i soindole- 1 ,3 (27 / )-di on e and 1 , 3 -Dihy dro-2H- isoindole-1, 3-dione, and a dispersant, wherein the reaction of step b. optionally includes an antifoam agent such as a silicon oil-based anti-foam agent compound.

[0248] 2. The process of statement 1 wherein, a. the dispersed reactant mixture comprises a sulphonate-based dispersant, b. the dispersed reactant mixture comprises an antifoaming agent such as, a silicon oil-based compound, c. the solid particles of nitrogen compound are finely divided particles selected from 3a,4,7,7a-Tetrahydro-lH-isoindole-l,3(2H)-dione and 1,3- Dihydro-2H-i soindole- 1,3 -di one particles, d. the phthalimide based fungicide obtained is folpet, captan or captafol, e. the aqueous alkaline solution is an aqueous solution of an alkali metal hydroxide, f. the aqueous alkaline solution is an aqueous solution of a metal salt of a carbonate, g. the aqueous alkaline solution is an aqueous solution of an alkali metal hydroxide or a metal salt of a carbonate and the concentration of the aqueous alkali metal hydroxide or metal salt of carbonate in the solution is between about 13% and about 31%, h. the aqueous alkaline solution is a sodium hydroxide aqueous solution and the salt obtained in step b. is a sodium salt of 3a,4,7,7a-Tetrahydro-lH- isoindole-l,3(2H)-dione or a sodium salt of l,3-Dihydro-2H-isoindole- 1,3 -di one, i. the reaction of the dispersed reactant mixture of step a. with the aqueous alkaline solution in reacting step b. to obtain a salt, is completed in 2 minutes or less, j. the aqueous alkaline solution in step b. is a sodium hydroxide aqueous solution and the salt obtained in step b. is a sodium salt of the nitrogen compound, 3a,4,7,7a-Tetrahydro-lH-isoindole-l,3(2H)-dione or a sodium salt of the nitrogen compound, l,3-Dihydro-2H-isoindole-l, 3-dione wherein, the molar ratio between the sodium hydroxide and the nitrogen compound particles and is about 1.05: 1 and a yield of about 90% or more of sodium salt of the nitrogen compound is achieved in a reaction time not exceeding 2 minutes, k. preparing the dispersed reactant mixture of step a, and reacting the obtained reactant mixture with aqueous alkaline solution to obtain a salt of step b., occurs simultaneously, in parallel, or concurrently, wherein the solid particles of nitrogen compound, 3a,4,7,7a-Tetrahydro-lH-isoindole- l,3(2H)-dione or l,3-Dihydro-2H-isoindole-l, 3-dione; dispersant; aqueous media, or water; and aqueous alkaline solution, are combined as a reaction combination in a reaction space optionally, with an antifoam agent, within which the solid particles of nitrogen compound are mixed and dispersed in the aqueous media or water and reacted with the alkaline solution within the same period of residence in the reaction space, preparing the dispersed reactant mixture of step a, and reacting the obtained reactant mixture with aqueous alkaline solution to obtain a salt of step b., occurs simultaneously, in parallel, or concurrently, wherein the nitrogen compound, 3a,4,7,7a-Tetrahydro-lH-isoindole-l,3(2H)-dione or l,3-Dihydro-2H-isoindole-l, 3-dione; dispersant; aqueous media, or water; and aqueous alkaline solution, are combined as a reaction combination in a reaction space optionally with an antifoam agent, within which, the nitrogen compound is reduced to a finely divided solid particulate and dispersed in the aqueous media or water at high shear and reacted within the same period of residence in the reaction space, m. reacting the reactant mixture of step a. with aqueous alkaline solution to obtain a salt, achieves a yield exceeding about 90% or more after a reaction time that does not exceed 2 minutes, and / or n. the ratio between the weight of the nitrogen compound of the dispersed reactant mixture obtained in step a. to the combined volumes of water from the dispersed reactant mixture and from the aqueous alkaline solution of step b. is between about 1 :5 to about 1 :6.5 w / v. The process of statement 1 or 2, wherein, the dispersed reactant mixture comprises a sulphonate-based dispersant. The process of statement 1 or 2, wherein, the dispersed reactant mixture comprises a lignosulphonate dispersant. The process of statements 1 or 2, wherein, the dispersed reactant mixture comprises finely divided solid particles of 3a,4,7,7a-Tetrahydro-lH-isoindole- l,3(2H)-dione characterized by a particle size distribution such that the D50 value is 50 microns or less, more typically between about 0.1pm to about 50 pm. The process of statements 1 or 2, wherein, the dispersed reactant mixture comprises finely divided solid particles of l,3-Dihydro-2H-isoindole-l,3- dione characterized by a particle size distribution such that the D50 value is 50 microns or less, more typically between about 0.1 pm to about 50 pm. A dispersed reactant mixture for use in the process of either statement 1 or statement 2, comprising an aqueous dispersion or suspension of finely divided solid particles of 3a,4,7,7a-Tetrahydro-lH-isoindole-l,3(2H)-dione or of 1,3- Dihydro-2H-isoindole-l, 3-dione and a lignosulphonate dispersant, optionally further comprising an antifoam agent.

[0249] 8. The dispersed reactant mixture of statement 7 wherein the finely divided solid particles of 3a,4,7,7a-Tetrahydro-lH-isoindole-l,3(2H)-dione or of 1,3- Dihydro-2H-isoindole-l, 3-dione are characterized by a particle size distribution such that the D50 (median) value is 50 micron or less, such as, between about 0.1pm and about 50pm or between about 1pm and about 50pm.

[0250] 9. A process for producing phthalimide based fungicide which comprises

[0251] (1) preparing a water-based dispersion comprising a. a nitrogen compound selected from i. 3a,4,7,7a-Tetrahydro-17 / -isoindole-l,3(2J7)-dione and ii. l,3-Dihydro-2H-isoindole-l, 3-dione and b. Sulfonate-based dispersant,

[0252] (2) reacting the dispersion of step (1) with aqueous alkaline solution,

[0253] (3) reacting the resulting salt with mercapto-based compound selected from the group of perchloromethyl mercaptan (PCMM) and pentachloroethyl mercaptan (PCEM) and

[0254] (4) isolation of the phthalimide based fungicide.

[0255] 10. A process for producing salts of nitrogen compound selected from group of 3 a, 4, 7,7a-T etrahy dro- 1 H soindole- 1 ,3 (27 / )-di on e and 1 , 3 -Dihy dro-2H- isoindole-1, 3-dione comprising

[0256] (1) preparing a water-based dispersion comprising

[0257] (a) nitrogen compound selected from group of 3a,4,7,7a-Tetrahydro-17 / -isoindole-l,3(2J7)-dione and 1 ,3 -Dihydro-2H-isoindole- 1 ,3 -di one and

[0258] (b) sulfonate-based dispersant and

[0259] (2) reacting the dispersion of step (1) with aqueous alkaline solution. The process of statement 9 or 10, wherein the phthalimide based fungicide comprises N-trichloromethylthio-tetrahydro phthalimide. The process of statement 9 or 10, wherein the phthalimide based fungicide comprises N-trichloromethylthio-phthalimide. The process of statement 9 or 10, wherein the phthalimide based fungicide comprises N-tri chloromethylthio-succinimide. The process of any one of statements 1-5, wherein the dynamic viscosity of the dispersion obtained in step (1) is less than 10 Pa*s (pascal second). The process of any one of statements 9-14, wherein the sulfonate-based dispersant comprises a poly sulfonate structure. The process of any one of statements 9-14, wherein the sulfonate-based dispersant comprises a lignosulfonate. The process of any one of statements 9-14, wherein the sulfonate-based dispersant comprises an Alkylnaphthalene sulfonate (ANS) condensate blend such as with wetting agent. The process of any one of statements 9-14, wherein the sulfonate-based dispersant comprises a low molecular weight kraft lignosulfonate with a low degree of sulfonation such as Polyfon H. The process of any one of statements 1-6, wherein the sulfonate-based dispersant comprises a highly sulfonated kraft lignin such as Reax 100M. The process of any one of statements 1-6, wherein, the sulfonate-based dispersant comprises a sodium salt of a chemically modified low molecular weight kraft lignin polymer solubilized by five sulfonate groups such as, Reax 88A. The process of any one of statements 1-6, wherein the sulfonate-based dispersant is Sodium Lignosulphonate CAS No. 8061-51-6 such as, Borresperse Na which contains up to 7% water. The process of statement 17, wherein the Alkylnaphthalene sulfonate (ANS) condensate blend is a blend of sodium salt of naphthalene sulfonate condensate (NSC) and wetting agent such as a block copolymer such as Morwet D-450. The process of any one of statements 9-22, wherein the ratio between the weight of the solid particles of nitrogen compound to the total volume of water for dissolving the salt obtained in step (2) is between about 1 :5 to about 1 :6.5 w / v. The process of any one of statements 9-23, wherein the nitrogen compound is 3a,4,7,7a-Tetrahydro-U / -isoindole-l,3(2J7)-dione. The process of any one of statements 9-23, wherein the nitrogen compound is 1 ,3 -Dihydro-2H-isoindole- 1 ,3 -di one. The process of statement 24, wherein when the nitrogen compound comprises 3a,4,7,7a-Tetrahydro-U / -isoindole-l,3(2J7)-dione, the ratio between the obtained 3a,4,7,7a-Tetrahydro-U / -isoindole-l,3(2J7)-dione salt and water is between about 1 :5 to about 1 :5.5 w / v. The process of statement 24, wherein when the nitrogen compound comprises l,3-Dihydro-2H-isoindole-l, 3-dione (phthalimide), the ratio between the phthalimide salt and water is between about 1:6 to about 1 :6.5 w / v. The process of any one of statements 9-27, wherein step (1) and / or (2) is conducted in presence of antifoaming agent. The process of any one of statements 9-28, wherein step (1) and / or (2) is conducted at temperature of about 0-15°C. The process of statement 29, wherein step (1) and / or (2) is conducted at temperature of about 0-5°C. The process of any one of statements 9-30, wherein the process is a continuous process. The process of any one of statements 9-30, wherein the process is a batch process. The process of any one of statements 9-32, wherein step (1) includes steps (li) dissolving, or otherwise solubilizing the sulfonate-based dispersant in water to obtain solution, |(lii) adding the nitrogen compound selected from group consisting of 3a,4,7,7a-Tetrahydro-l / Z-isoindole-l,3(2J7)-dione and 1,3- Dihydro-2H-isoindole-l, 3-dione and |(liii) stirring for a period such as for at least 10 min. The process of statement 33, wherein the temperature of the solution obtained in step |(li) is between about 0°C and about 10°C. The process of any one of statements 9- 34, wherein the sulfonate-based dispersant comprises about 0.05-0.4% w / w based on the weight of the nitrogen compound. The process of statement 35, wherein the sulfonate-based dispersant comprises about 0.2-0.4% w / w based on the weight of the nitrogen compound. The process of any one of statements 9-36, wherein the weight ratio between the water to the nitrogen compound, which comprises 3a,4,7,7a-Tetrahydro- lH-isoindole-l,3(2H)-dione in step (1) is about 3.5 : 1 to about 4: 1. The process of any one of statements 9-36, wherein the weight ratio between the water to the nitrogen compound which comprises 177-isoindole-l, 3(277)- dione in step (1) is about 4.5: 1 to about 5: 1. The process of any one of statements 9-38, wherein the concentration of the aqueous alkaline solution is about 15% - 28%. The process of any one of statements 9-39, wherein the aqueous alkaline solution comprises an aqueous solution of metal salt of carbonate. The process of any one of statements 9-39, wherein the aqueous alkaline solution comprises an aqueous solution of a metal salt of hydroxide. The process of statement 41, wherein the alkali hydroxide comprises sodium hydroxide. The process of statement 40, wherein the molar ratio between the nitrogen compound and the carbonate is between about 1 : 1 to about 1 : 1.4. The process of statement 41 or 42 wherein the molar ratio between the nitrogen compound and the hydroxide is between about 1 : 1 to about 1 : 1.4. The process of any one of statements 9-44, wherein step (2) is conducted in presence of an antifoaming agent. The process of any one of statements 9-45, wherein step (2) is conducted at temperature of about 0-15°C. The process of statement 46, wherein step (2) is conducted at temperature of about 0-5°C. The process of any one of statements 9-47, wherein the time for conducting step (2) less than 1 minute. 9. The process of any one of statements 9-48, wherein the nitrogen compound is in its solid form. 0. The process of statement 49, wherein solid form of the nitrogen compound used for preparing the water-based dispersion in step (1) is as flakes with particle sizes between about 200 microns to about 4 mm. 1. The process of any one of statements 9-50, wherein the solid particles of nitrogen compound when they are reacted in step (2) as the dispersion obtained in step (1) with the aqueous alkaline solution have a particle size distribution characterized by a D50 value of 50 microns or less. 2. The process of statement 51, wherein the particle size distribution is achieved by milling, such as passage through a mill or though one or more high shear pumps. 3. The process of statement 52, wherein the milling of the particles is conduction in parallel to the addition of the aqueous alkaline solution. 4. The process of any one of statements 9-53, wherein step (2) is conducted in, or through, one or more high shear pumps. The process of any one of statements 9-54, wherein step (2) is conducted in, or through, one or more high shear pumps. The process of any one of statements 1-6, wherein step (b) is conducted in, or through, one or more high shear pumps. 7. The process of any one of statements 9-55, wherein step (2) conducted at least 2 times wherein the total combined time for the reaction of the nitrogen compound with the aqueous alkaline solution is up to 1 min. 8. The process of any one of statements 9-56, wherein the reaction with the aqueous alkaline solution is by using 2 or more In-line High shear pumps in series. The process of any one of statements 9-56, wherein the reaction with the aqueous alkaline solution is by multiple passages through a High Shear pump or media mill. The process of any one of statements 56-57, wherein the reaction with the aqueous alkaline solution and the reduction of the particle size distribution of the nitrogen compound occurs simultaneously or concomitantly within In-line High shear pumps. An aqueous dispersion or suspension of finely divided solid particles of 3a,4,7,7a-Tetrahydro-lH-isoindole-l,3(2H)-dione or of 1,3-Dihydro-2H- isoindole-1, 3-dione, lignosulphonate dispersant, and a antifoam agent comprising a polydimethylsiloxane oil. The process of statement 1, comprising, a. combining and mixing within a reaction space, i. nitrogen compound selected from 3a,4,7,7a-Tetrahydro-lH- isoindole-l,3(2H)-dione or l,3-Dihydro-2H-isoindole-l,3- dione; ii. sulphonate-dispersant such as Sodium Lignosulphonate; iii. aqueous media, or water; iv. aqueous alkaline solution such as Sodium Hydroxide solution; and optionally, v. antifoam agent such as a polydimethylsiloxane oil, to form a reaction combination in the reaction space and thus obtain salt of the nitrogen compound in aqueous solution, wherein the total volume of water of the reaction combination is sufficient to dissolve the salt of the nitrogen compound, such as wherein the ratio between the weight of the nitrogen compound to the combined volumes of water from of parts iii. and iv. in the reaction space is between about 1 :5 to about 1 :6.5 w / v, b. reacting the obtained aqueous salt from step b. with PCMM or PCEM to obtain phthalimide based fungicide.

[0260] 63. The process of either statement 1 or statement 62, comprising, a. introducing into the internal space within one or more high shear pumps, i. a combination of nitrogen compound selected from 3a, 4, 7,7a- Tetrahydro-lH-isoindole-l,3(2H)-dione or 1,3-Dihydro-2H- isoindole-1, 3-dione, sulphonate-dispersant such as Sodium Lignosulphonate, and aqueous media, or water, ii. an aqueous alkali solution such as NaOH solution, and optionally iii. antifoam agent such as polydimethylsiloxane oil, operating the one or more high shear pumps so as to concomitantly, reduce the 3a,4,7,7a-Tetrahydro-lH-isoindole-l,3(2H)-dione or 1,3- Dihydro-2H-isoindole-l,3-dione to a finely dispersed particulate slurry, and mix and react the slurry with the aqueous alkali solution under high shear, to thus obtain an aqueous solution of 3a,4,7,7a-Tetrahydro-lH- isoindole-l,3(2H)-dione salt or l,3-Dihydro-2H-isoindole-l, 3-dione salt during the residence time within the operating high shear pump, b. pumping the obtained aqueous solution of 3a,4,7,7a-Tetrahydro-lH- isoindole-l,3(2H)-dione salt or aqueous solution of 1,3-Dihydro-2H- isoindole-1, 3-dione salt, out of the internal space from within the high shear pump, optionally into the internal space within an additional high shear pump preferably in fluid connection and / or via additional passage through the internal space of the high shear pump, and c. reacting the obtained aqueous salt solution from step b. with PCMM or PCEM to obtain phthalimide based fungicide, wherein the total residence time within the internal space(s) of the high shear pump(s) need not exceed a period of more than 2 minutes for completion of the conversion of the nitrogen compound to the salt of 3a,4,7,7a-Tetrahydro-lH-isoindole-l,3(2H)- dione or salt of l,3-Dihydro-2H-isoindole-l, 3-dione.

Claims

Claims1. A process for producing phthalimide based fungicide employing a dispersed reactant mixture comprising, a. preparing a dispersed reactant mixture, b. reacting the obtained reactant mixture of step a. with aqueous alkaline solution to obtain a salt, preferably in aqueous solution, c. reacting the resulting salt from step b. with mercapto-based compound selected from perchloromethyl mercaptan (PCMM) and pentachloro ethyl mercaptan (PCEM) to obtain phthalimide based fungicide, and optionally, d. isolation and purification of the phthalimide based fungicide obtained in step c. , wherein the dispersed reactant mixture is a water-based dispersion or aqueous suspension comprising solid particles of a nitrogen compound selected from 3 a, 4, 7,7a-T etrahy dro- 17 / -i soindole- 1 ,3 (27 / )-di on e and 1 , 3 -Dihy dro-2H- isoindole-1, 3-dione, and a dispersant, wherein the reaction of step b. optionally includes an antifoam agent such as a silicon oil-based anti-foam agent compound.

2. The process of claim 1 wherein, a. the dispersed reactant mixture comprises a sulphonate-based dispersant, b. the dispersed reactant mixture comprises an antifoaming agent such as, a silicon oil-based compound, c. the solid particles of nitrogen compound are finely divided particles selected from 3a,4,7,7a-Tetrahydro-lH-isoindole-l,3(2H)-dione and 1,3- Dihydro-2H-i soindole- 1,3 -di one particles, d. the phthalimide based fungicide obtained is folpet, captan or captafol, e. the aqueous alkaline solution is an aqueous solution of an alkali metal hydroxide, f. the aqueous alkaline solution is an aqueous solution of a metal salt of a carbonate, g. the aqueous alkaline solution is an aqueous solution of an alkali metal hydroxide or a metal salt of a carbonate and the concentration of theaqueous alkali metal hydroxide or metal salt of carbonate in the solution is between about 13% and about 31%, h. the aqueous alkaline solution is a sodium hydroxide aqueous solution and the salt obtained in step b. is a sodium salt of 3a,4,7,7a-Tetrahydro-lH- isoindole-l,3(2H)-dione or a sodium salt of l,3-Dihydro-2H-isoindole-1.3 -di one, i. the reaction of the dispersed reactant mixture of step a. with the aqueous alkaline solution in reacting step b. to obtain a salt, is completed in 2 minutes or less, j. the aqueous alkaline solution in step b. is a sodium hydroxide aqueous solution and the salt obtained in step b. is a sodium salt of the nitrogen compound, 3a,4,7,7a-Tetrahydro-lH-isoindole-l,3(2H)-dione or a sodium salt of the nitrogen compound, l,3-Dihydro-2H-isoindole-l, 3-dione wherein, the molar ratio between the sodium hydroxide and the nitrogen compound particles and is about 1.05: 1 and a yield of about 90% or more of sodium salt of the nitrogen compound is achieved in a reaction time not exceeding 2 minutes, k. preparing the dispersed reactant mixture of step a., and reacting the obtained reactant mixture with aqueous alkaline solution to obtain a salt of step b., occurs simultaneously, in parallel, or concurrently, wherein the solid particles of nitrogen compound, 3a,4,7,7a-Tetrahydro-lH-isoindole- l,3(2H)-dione or l,3-Dihydro-2H-isoindole-l, 3-dione; dispersant; aqueous media, or water; and aqueous alkaline solution, are combined as a reaction combination in a reaction space optionally, with an antifoam agent, within which the solid particles of nitrogen compound are mixed and dispersed in the aqueous media or water and reacted with the alkaline solution within the same period of residence in the reaction space,1. preparing the dispersed reactant mixture of step a, and reacting the obtained reactant mixture with aqueous alkaline solution to obtain a salt of step b., occurs simultaneously, in parallel, or concurrently, wherein the nitrogen compound, 3a,4,7,7a-Tetrahydro-lH-isoindole-l,3(2H)-dione or1.3-Dihydro-2H-isoindole-l, 3-dione; dispersant; aqueous media, or water; and aqueous alkaline solution, are combined as a reaction combination in a reaction space optionally with an antifoam agent, within which, thenitrogen compound is reduced to a finely divided solid particulate and dispersed in the aqueous media or water at high shear and reacted within the same period of residence in the reaction space, m. reacting the reactant mixture of step a. with aqueous alkaline solution to obtain a salt, achieves a yield exceeding about 90% or more after a reaction time that does not exceed 2 minutes, and / or n. the ratio between the weight of the nitrogen compound of the dispersed reactant mixture obtained in step a. to the combined volumes of water from the dispersed reactant mixture and from the aqueous alkaline solution of step b. is between about 1 :5 to about 1 :6.5 w / v.

3. The process of claim 1 or 2, wherein, the dispersed reactant mixture comprises a sulphonate-based dispersant.

4. The process of claim 1 or 2, wherein, the dispersed reactant mixture comprises a lignosulphonate dispersant.

5. The process of claim 1 or 2, wherein, the dispersed reactant mixture comprises finely divided solid particles of 3a,4,7,7a-Tetrahydro-lH-isoindole-l,3(2H)- dione characterized by a particle size distribution such that the D50 value is 50 microns or less, more typically between about 0.1 pm to about 50 pm.

6. The process of claim 1 or 2, wherein, the dispersed reactant mixture comprises finely divided solid particles of l,3-Dihydro-2H-isoindole-l,3-dione characterized by a particle size distribution such that the D50 value is 50 microns or less, more typically between about 0.1 pm to about 50 pm.

7. A dispersed reactant mixture for use in the process of either claim 1 or claim 2, comprising an aqueous dispersion or suspension of finely divided solid particles of 3a,4,7,7a-Tetrahydro-lH-isoindole-l,3(2H)-dione or of 1,3- Dihydro-2H-isoindole-l, 3-dione and a lignosulphonate dispersant, optionally further comprising an antifoam agent.

8. The dispersed reactant mixture of claim 7 wherein the finely divided solid particles of 3a,4,7,7a-Tetrahydro-lH-isoindole-l,3(2H)-dione or of 1,3- Dihydro-2H-isoindole-l, 3-dione are characterized by a particle size distribution such that the D50 (median) value is 50 micron or less, such as, between about 0.1pm and about 50pm or between about 1pm and about 50pm.

9. A process for producing phthalimide based fungicide which comprises(1) preparing a water-based dispersion comprising a. a nitrogen compound selected from i. 3a,4,7,7a-Tetrahydro-17 / -isoindole-l,3(2J7)-dione and ii. l,3-Dihydro-2H-isoindole-l, 3-dione and b. sulfonate-based dispersant,(2) reacting the dispersion of step (1) with aqueous alkaline solution,(3) reacting the resulting salt with mercapto-based compound selected from the group of perchloromethyl mercaptan (PCMM) and pentachloro ethyl mercaptan (PCEM) and(4) isolation of the phthalimide based fungicide.

10. A process for producing salts of nitrogen compound selected from group of 3 a, 4, 7,7a-T etrahy dro- 1 H soindole- 1 ,3 (27 / )-di on e and 1 , 3 -Dihy dro-2H- isoindole-1, 3-dione comprising(1) preparing a water-based dispersion comprising(a) nitrogen compound selected from group of 3a,4,7,7a-Tetrahydro-17 / -isoindole-l,3(2J7)-dione and 1 ,3 -Dihydro-2H-isoindole- 1 ,3 -di one and(b) sulfonate-based dispersant and(2) reacting the dispersion of step (1) with aqueous alkaline solution.

11. The process of claim 9 or 10, wherein the phthalimide based fungicide comprises N-trichloromethylthio-tetrahydro phthalimide.

12. The process of claim 9 or 10, wherein the phthalimide based fungicide comprises N-trichloromethylthio-phthalimide.

13. The process of claim 9 or 10, wherein the phthalimide based fungicide comprises N-tri chloromethylthio-succinimide.

14. The process of any one of claims 1-5, wherein the dynamic viscosity of the dispersion obtained in step (1) is less than 10 Pa*s (pascal second).

15. The process of any one of claims 9-14, wherein the sulfonate-based dispersant comprises a poly sulfonate structure.

16. The process of any one of claims 9-14, wherein the sulfonate-based dispersant comprises a lignosulfonate.

17. The process of any one of claims 9-14, wherein the sulfonate-based dispersant comprises an Alkylnaphthalene sulfonate (ANS) condensate blend such as with wetting agent.

18. The process of any one of claims 9-14, wherein the sulfonate-based dispersant comprises a low molecular weight kraft lignosulfonate with a low degree of sulfonation such as Polyfon H.

19. The process of any one of claims 1-6, wherein the sulfonate-based dispersant comprises a highly sulfonated kraft lignin such as Reax 100M.

20. The process of any one of claims 1-6, wherein, the sulfonate-based dispersant comprises a sodium salt of a chemically modified low molecular weight kraft lignin polymer solubilized by five sulfonate groups such as, Reax 88 A.

21. The process of any one of claims 1-6, wherein the sulfonate-based dispersant is Sodium Lignosulphonate CAS No. 8061-51-6 such as, Borresperse Na which contains up to 7% water.

22. The process of claim 17, wherein the Alkylnaphthalene sulfonate (ANS) condensate blend is a blend of sodium salt of naphthalene sulfonate condensate (NSC) and wetting agent such as a block copolymer such as Morwet D-450.

23. The process of any one of claims 9-22, wherein the ratio between the weight of the solid particles of nitrogen compound to the total volume of water for dissolving the salt obtained in step (2) is between about 1 :5 to about 1 :6.5 w / v.

24. The process of any one of claims 9-23, wherein the nitrogen compound is 3a,4,7,7a-Tetrahydro-U / -isoindole-l,3(2J7)-dione.

25. The process of any one of claims 9-23, wherein the nitrogen compound is 1,3- Dihy dro-2H-i soindole- 1 , 3 -di one .

26. The process of claim 24, wherein when the nitrogen compound comprises 3a,4,7,7a-Tetrahydro-U / -isoindole-l,3(2J7)-dione, the ratio between the obtained 3a,4,7,7a-Tetrahydro-U / -isoindole-l,3(2J7)-dione salt and water is between about 1 :5 to about 1 :5.5 w / v.

27. The process of claim 24, wherein when the nitrogen compound comprises 1,3- Dihydro-2H-isoindole-l, 3-dione (phthalimide), the ratio between the phthalimide salt and water is between about 1 :6 to about 1 :6.5 w / v.

28. The process of any one of claims 9-27, wherein step (1) and / or (2) is conducted in presence of antifoaming agent.

29. The process of any one of claims 9-28, wherein step (1) and / or (2) is conducted at temperature of about 0-15°C.

30. The process of claim 29, wherein step (1) and / or (2) is conducted at temperature of about 0-5°C.

31. The process of any one of claims 9-30, wherein the process is a continuous process.

32. The process of any one of claims 9-30, wherein the process is a batch process.

33. The process of any one of claims 9-32, wherein step (1) includes steps (li) dissolving, or otherwise solubilizing the sulfonate-based dispersant in water to obtain solution, |(lii) adding the nitrogen compound selected from group consisting of 3a,4,7,7a-Tetrahydro-l / Z-isoindole-l,3(2J7)-dione and 1,3- Dihydro-2H-isoindole-l, 3-dione and |(liii) stirring for a period such as for at least 10 min.

34. The process of claim 33, wherein the temperature of the solution obtained in step |(li) is between about 0°C and about 10°C.

35. The process of any one of claims 9- 34, wherein the sulfonate-based dispersant comprises about 0.05-0.4% w / w based on the weight of the nitrogen compound.

36. The process of claim 35, wherein the sulfonate-based dispersant comprises about 0.2-0.4% w / w based on the weight of the nitrogen compound.

37. The process of any one of claims 9-36, wherein the weight ratio between the water to the nitrogen compound, which comprises 3a,4,7,7a-Tetrahydro-lH- isoindole-l,3(2H)-dione in step (1) is about 3.5 : 1 to about 4: 1.

38. The process of any one of claims 9-36, wherein the weight ratio between the water to the nitrogen compound which comprises IT / -isoindole- l ,3(27 / )-dione in step (1) is about 4.5: 1 to about 5: 1.

39. The process of any one of claims 9-38, wherein the concentration of the aqueous alkaline solution is about 15% - 28%.

40. The process of any one of claims 9-39, wherein the aqueous alkaline solution comprises an aqueous solution of metal salt of carbonate.

41. The process of any one of claims 9-39, wherein the aqueous alkaline solution comprises an aqueous solution of a metal salt of hydroxide.

42. The process of claim 41, wherein the alkali hydroxide comprises sodium hydroxide.

43. The process of claim 40, wherein the molar ratio between the nitrogen compound and the carbonate is between about 1 : 1 to about 1 : 1.4.

44. The process of claim 41 or 42 wherein the molar ratio between the nitrogen compound and the hydroxide is between about 1 : 1 to about 1 : 1.4.

45. The process of any one of claims 9-44, wherein step (2) is conducted in presence of an antifoaming agent.

46. The process of any one of claims 9-45, wherein step (2) is conducted at temperature of about 0-15°C.

47. The process of claim 46, wherein step (2) is conducted at temperature of about 0-5°C.

48. The process of any one of claims 9-47, wherein the time for conducting step (2) less than 1 minute.

49. The process of any one of claims 9-48, wherein the nitrogen compound is in its solid form.

50. The process of claim 49, wherein solid form of the nitrogen compound used for preparing the water-based dispersion in step (1) is as flakes with particle sizes between about 200 microns to about 4 mm.

51. The process of any one of claims 9-50, wherein the solid particles of nitrogen compound when they are reacted in step (2) as the dispersion obtained in step (1) with the aqueous alkaline solution have a particle size distribution characterized by a D50 value of 50 microns or less.

52. The process of claim 51, wherein the particle size distribution is achieved by milling, such as passage through a mill or though one or more high shear pumps.

53. The process of claim 52, wherein the milling of the particles is conduction in parallel to the addition of the aqueous alkaline solution.

54. The process of any one of claims 9-53, wherein step (2) is conducted in, or through, one or more high shear pumps.

55. The process of any one of claims 9-54, wherein step (2) is conducted in, or through, one or more high shear pumps.

56. The process of any one of claims 1-6, wherein step (b) is conducted in, or through, one or more high shear pumps.

57. The process of any one of claims 9-55, wherein step (2) conducted at least 2 times wherein the total combined time for the reaction of the nitrogen compound with the aqueous alkaline solution is up to 1 min.

58. The process of any one of claims 9-56, wherein the reaction with the aqueous alkaline solution is by using 2 or more In-line High shear pumps in series.

59. The process of any one of claims 9-56, wherein the reaction with the aqueous alkaline solution is by multiple passages through a High Shear pump or media mill.

60. The process of any one of claims 56-57, wherein the reaction with the aqueous alkaline solution and the reduction of the particle size distribution of thenitrogen compound occurs simultaneously or concomitantly within In-line High shear pumps.

61. An aqueous dispersion or suspension of finely divided solid particles of 3a,4,7,7a-Tetrahydro-lH-isoindole-l,3(2H)-dione or of 1,3-Dihydro-2H- isoindole-1, 3-dione, lignosulphonate dispersant, and a antifoam agent comprising a polydimethylsiloxane oil.

62. The process of claim 1, comprising, a. combining and mixing within a reaction space, i. nitrogen compound selected from 3a,4,7,7a-Tetrahydro-lH- isoindole-l,3(2H)-dione or l,3-Dihydro-2H-isoindole-l,3- dione; ii. sulphonate-dispersant such as Sodium Lignosulphonate; iii. aqueous media, or water; iv. aqueous alkaline solution such as Sodium Hydroxide solution; and optionally, v. antifoam agent such as a polydimethylsiloxane oil, to form a reaction combination in the reaction space and thus obtain salt of the nitrogen compound in aqueous solution, wherein the total volume of water of the reaction combination is sufficient to dissolve the salt of the nitrogen compound, such as wherein the ratio between the weight of the nitrogen compound to the combined volumes of water from of parts iii. and iv. in the reaction space is between about 1 :5 to about 1 :6.5 w / v, b. reacting the obtained aqueous salt from step b. with PCMM or PCEM to obtain phthalimide based fungicide.

63. The process of either claim 1 or claim 62, comprising, a. introducing into the internal space within one or more high shear pumps, i. a combination of nitrogen compound selected from 3a, 4, 7,7a- Tetrahydro-lH-isoindole-l,3(2H)-dione or 1,3-Dihydro-2H- isoindole-1, 3-dione, sulphonate-dispersant such as Sodium Lignosulphonate, and aqueous media, or water,ii. an aqueous alkali solution such as NaOH solution, and optionally iii. antifoam agent such as polydimethylsiloxane oil, operating the one or more high shear pumps so as to concomitantly, reduce the 3a,4,7,7a-Tetrahydro-lH-isoindole-l,3(2H)-dione or 1,3- Dihydro-2H-isoindole-l,3-dione to a finely dispersed particulate slurry, and mix and react the slurry with the aqueous alkali solution under high shear, to thus obtain an aqueous solution of 3a,4,7,7a-Tetrahydro-lH- isoindole-l,3(2H)-dione salt or l,3-Dihydro-2H-isoindole-l, 3-dione salt during the residence time within the operating high shear pump, b. pumping the obtained aqueous solution of 3a,4,7,7a-Tetrahydro-lH- isoindole-l,3(2H)-dione salt or aqueous solution of 1,3-Dihydro-2H- isoindole-1, 3-dione salt, out of the internal space from within the high shear pump, optionally into the internal space within an additional high shear pump preferably in fluid connection and / or via additional passage through the internal space of the high shear pump, and c. reacting the obtained aqueous salt solution from step b. with PCMM or PCEM to obtain phthalimide based fungicide, wherein the total residence time within the internal space(s) of the high shear pump(s) need not exceed a period of more than 2 minutes for completion of the conversion of the nitrogen compound to the salt of 3a,4,7,7a-Tetrahydro- lH-isoindole-l,3(2H)-dione or salt of l,3-Dihydro-2H-isoindole-l, 3-dione.