TWI613967B - Soluble granule containing active ingredient of sulfonamide free acid - Google Patents

Description

Soluble granule containing active ingredient of sulfonamide free acid

The invention relates to a pesticide soluble granule. In particular, the invention relates to soluble granules comprising at least one sulfonamide herbicide free acid active component.

Sulfonamide herbicides act by inhibiting acetolactate synthase (ALS) present in plants but not in animals, so sulfonamide herbicides provide excellent herbicidal activity at low levels while being low in animals. poison.

The sulfonamide herbicide is a highly active type of herbicide. It can be processed into a variety of different forms of concentrates, as well as other solid compositions, including liquid compositions of emulsifiable concentrates and solid compositions such as wettable powders and water-dispersible granules.

The liquid composition can be easily transferred and measured, but the emulsion has a large amount of residue in the spray tank. Sulfonamide is a highly active herbicide. It is therefore necessary to clean the spray device before using the spray device for treating crops that are sensitive to the sulfonamide herbicide. Cleaning requires a rinsing step that is time consuming and produces wastewater, where proper environmental treatment of the wastewater is required. Moreover, if the spray equipment contains organic residues from previous crop protection chemical application residues or other chemicals that are mixed with the sulfonamide herbicide tank, the cleaning will be affected. A wettable powder containing a sulfonamide active ingredient, on the one hand, the dust affects the growth of adjacent sulfonamide herbicide-sensitive crops, and on the other hand, the sulfonamide herbicide remaining in the spray equipment The problem of pollution. The water-dispersible granules containing the sulfonamide active component are relatively dust-free compared to the wettable powder, but there are also spray coatings The problem of residual sulfonamide herbicide contamination.

PCT Patent Application Publication No. WO9316596 describes a method for reducing residual sulfonamide herbicide contamination in a spray apparatus, the first step of which requires that the formulation of the sulfonamide active ingredient be in the form of an agriculturally suitable water soluble salt. Although various methods are known for preparing salts of sulfonamide herbicides from the corresponding free acids, as is the method of preparing the active ingredient of the sulfonamide herbicide, which generally provides the free acid form either directly or as part of the separation, but conversion to salt requires additional Processing steps.

The present invention provides a soluble granule comprising at least one sulfonamide herbicide free acid active component. The soluble granules have no dust compared with the wettable powder; compared with the ordinary water-dispersible granules, the spray liquid obtained after dilution with water is clear and transparent, after the spraying, because the sulfonamide is in the spray tank The residue is small, the spray bucket is easy to clean, and the problem of contamination of the sulfonamide herbicide remaining in the spray equipment is reduced.

It has now been found that the soluble granules of the present invention comprising at least one of the free acid active components of the sulfonamide herbicide not only have excellent water dispersibility, but also have significantly improved spray equipment cleanability.

The sulfonamide herbicide is a herbicide containing a high activity type because, since the sulfonamide herbicide is used in the previous application, it needs to be cleaned before the device is subsequently used to treat crops sensitive to the sulfonamide herbicide. The spray equipment. Cleaning requires a rinsing step that is time consuming and produces wastewater, where proper environmental treatment of the wastewater is required. Moreover, if the spray equipment contains previous crop protection chemicals, the residue is applied or weeded with sulfonamide. Organic precipitation of other chemical residues in the tank mix can affect cleaning. Because the sulfonamide-containing liquid composition, wettable powder, and water-dispersible granules are substantially suspensions or emulsions in a spray tank. The suspended sulfonamide particles can accumulate on the walls of the barrel and in the tube, or be retained by organic deposits that may be present in the barrel. If the subsequent spray tank mixture delivers the sulfonamide to the solution or suspension, the sensitive crop may be damaged. This problem is avoided by the addition of a solid base to the composition containing sulfonamide. Therefore, at normal usage rates, little or no sulfonamide particles accumulate on the inner surface of the barrel or are embedded in an organic deposition layer that may form on the surface.

Accordingly, the present invention provides a soluble granule comprising at least one sulfonamide herbicide free acid active component comprising: (i) 2-90% anhydrous basis weight of an activity comprising at least one sulfonamide herbicide free acid a component; (ii) 0-95% anhydrous basis weight of one or more additives selected from the group consisting of wetting agents, dispersing agents, lubricants, anti-caking agents, chemical stabilizers, and diluents; (iii) at least one The solid base is selected from the group consisting of sodium hydrogencarbonate, sodium carbonate, sodium hydrogen phosphate, sodium phosphate, potassium hydrogencarbonate, potassium hydrogen phosphate, potassium phosphate, potassium hydrogencarbonate, potassium hydroxide, sodium carbonate hydrate, sodium acetate, sodium tripolyphosphate, ten Sodium phosphate dihydrate, ammonium hydrogen phosphate, sodium citrate, sodium tricitrate, sodium polyphosphate, sodium hexametaphosphate, potassium pyrophosphate; the amount of solid base accounts for at least 1% of the pesticide composition, and the solid base and The weight ratio of the sulfonamide herbicide free acid is 1:90-90:1; the sum of the anhydrous base weight percentages of all components in the pesticide mixture is 100%. Solid bases include those having a cation derived from an alkali metal or ammonium and a counterion selected from the group consisting of carbonate, phosphate, oxide, hydroxide, acetate, and citrate anion, including dimeric, trimeric, and polymeric forms thereof. . For example, pyrophosphate, tripolyphosphate, polyphosphate, triterpene, and the like. Exemplary solid bases include, without limitation, sodium acetate (NaAC), sodium phosphate (Na ₂ PO ₄ ), sodium hydrogen phosphate (Na ₂ HPO ₄ ), potassium phosphate (K ₃ PO ₄ ), potassium hydrogen phosphate in anhydrous and hydrated forms. (KHPO ₄ ), ammonium hydrogen phosphate ((NH) ₂ HPO ₄ ), sodium carbonate (Na ₂ CO ₃ ), sodium hydrogencarbonate (NaHCO ₃ ), potassium carbonate (K ₂ CO ₃ ), potassium hydrogencarbonate (KHCO ₃ ) Lithium oxide (Li ₂ O), lithium hydroxide (LiOH), lithium carbonate (Li ₂ CO ₃ ), sodium hydroxide (NaOH), lithium phosphate (Li ₃ PO ₄ ), lithium niobate (Li ₂ SiO ₃ ) , raw lithium niobate (Li ₄ SiO ₄ ), potassium hydroxide (KOH), sodium citrate (Na ₂ SiO ₃ ), sodium decanoate (Na ₄ SiO ₄ ), potassium pyrophosphate (K ₄ P ₂ O ₇ ), sodium trimetaphosphate (NaP0 _{3) 3,} sodium hexametaphosphate ((NaPO _{3) 6),} sodium polyphosphate (NaP0 ₃₎ n, sodium pyrophosphate ^{_{(Na 4 P 2 O 7)}} , sodium tripolyphosphate ( Na ₅ P ₃ O ₁₀ ) and sodium tridecanoate (Na ₂ Si ₃ O ₇ ).

For reasons of cost, efficiency and convenience, a solid base preferably containing an alkali metal cation selected from the group consisting of sodium (Na+) and potassium (K+), more preferably sodium. Also preferably, for reasons of cost, efficiency and convenience, it is selected from the group consisting of acetate (AC-), bicarbonate (HCO ₃ -), carbonate (CO ₃ ^2- ), hydrogen phosphate (HPO ₄ ^2- ) and phosphoric acid. A solid base of a counterion of the root (PO ₄ ^3- ), more preferably a carbonate and a phosphate. Preferred solid bases include sodium acetate, sodium carbonate, sodium hydrogen phosphate, sodium phosphate, potassium hydrogencarbonate, potassium carbonate, potassium hydrogen phosphate. And potassium phosphate. The above solid base includes hydrated forms thereof, such as sodium carbonate monohydrate, sodium hydrogen phosphate hexahydrate, sodium phosphate dodecahydrate, potassium dihydrate hydrate, potassium hydrogen phosphate trihydrate and potassium octahydrate. Preferred are sodium carbonate, sodium phosphate, potassium carbonate and potassium phosphate, including the hydrated form thereof. The most preferred solid base is sodium carbonate, including the hydrated form thereof.

The present invention has found through a large number of experiments to improve specific sulfonamide active components. A solid base that is particularly effective in solubility in water.

The solid base includes sodium tripolyphosphate, sodium carbonate, sodium carbonate hydrate, sodium hydrogencarbonate, potassium hydrogencarbonate, potassium carbonate, sodium hydrogen phosphate, potassium hydroxide, sodium acetate or ammonium hydrogen phosphate for improving the solubility of mesulfuron in water. It is especially effective. Among them, sodium tripolyphosphate is the most suitable solid base relative to sulfometuron.

Solid bases including sodium bicarbonate, sodium acetate or sodium tripolyphosphate are particularly effective for increasing the solubility of the sulfometuron in water. Among them, sodium tripolyphosphate or sodium acetate is the most suitable solid base relative to rimsulfuron.

The solid base includes sodium tripolyphosphate, sodium carbonate, sodium carbonate hydrate, sodium hydrogencarbonate, potassium hydrogencarbonate, potassium carbonate, sodium hydrogen phosphate, potassium hydroxide, sodium acetate or ammonium hydrogen phosphate for improving the solubility of nicosulfuron in water. It is especially effective. Among them, sodium carbonate is the most suitable solid base relative to nicosulfuron.

Solid bases including sodium tripolyphosphate, sodium bicarbonate, potassium carbonate or potassium hydroxide are particularly effective for increasing the solubility of thifensulfuron in water. Among them, sodium tripolyphosphate is the most suitable solid base relative to thifensulfuron.

Solid base sodium tripolyphosphate, potassium carbonate or sodium hydrogencarbonate is particularly effective for increasing the solubility of bensulfuron in water.

Solid bases including sodium tripolyphosphate or sodium carbonate are particularly effective for increasing the solubility of metsulfuron in water.

By adding a sufficient amount of a solid base to the composition containing the sulfonamide active component, the solubility of the sulfonamide free acid active component in water can be improved to obtain a clear transparent water spray liquid containing a sulfonamide herbicide. Reduces the residue of sulfonamide in the spray tank. Solid base The amount required is based on the concentration of the active component of the sulfonamide free acid. The weight ratio of the solid base to the sulfonamide active component is from 1:90 to 90:1, and the amount of solid base is at least 1% by weight of the soluble granules containing the active component of the sulfonamide free acid.

The wetting agent contained in the soluble granule containing the free acid active component of the sulfonamide herbicide of the present invention includes, without limitation, alkyl sulfosuccinate, laurate, alkyl sulfate and phosphate, alkyne a diol, an ethoxylated alcohol, an ethoxylated oxane, an alkylphenol ethoxylate, a besylate, an alkyl substituted besylate, an alkyl a-olefin sulfonate, a naphthalene sulfonate, a condensate of an alkyl-substituted naphthalenesulfonate, a naphthalenesulfonate, and an alkyl-substituted naphthalenesulfonate with formaldehyde, and an alcohol ethoxylate. Representative compositions contain wetting agents up to 10% anhydrous basis weight.

Dispersing agents include, without limitation, sodium, calcium and ammonium salts of lignosulfonic acid (optionally polyethoxylated); sodium and ammonium salts of maleic anhydride copolymers; sodium salts of condensed phenolsulfonic acid; and naphthalenesulfonate-formaldehyde Condensate. Representative compositions contain up to 10% anhydrous basis weight of dispersant. Sodium lignosulfonate is especially suitable for use in the methods and compositions of the present invention.

The diluent can be water-soluble or water-insoluble, without limitation. The water soluble diluent can be a salt or a sugar that dissolves rapidly in water. Non-limiting examples include sodium dihydrogen phosphate, sodium, potassium, magnesium and zinc sulfates, sodium chloride and potassium chloride, sorbitol, sodium benzoate, lactose and sucrose. Water-insoluble diluents include, without limitation, clay, synthetic alumina and diatomaceous earth, calcium citrate and magnesium citrate, titanium oxide, aluminum oxide, calcium oxide and zinc oxide, calcium carbonate and magnesium carbonate, sodium sulfate, potassium sulfate, Calcium sulfate and barium sulfate, as well as charcoal. A water soluble diluent is preferred.

In addition to containing at least one sulfonamide free acid active component, at least one solid base and The diluent, the pesticidal composition may also suitably contain a stabilizer, a synergist, a colorant, and the like.

The pesticidal composition of the present invention may be in the form of a wettable powder, but is preferably in the form of a water-soluble granule. Similarly, the dry formulations of the present invention may be in the form of aggregates, matrices or whole bodies such as lumps, granules, tablets, sticks, films, sheets, and the like. The dry formulation of the invention is preferably embedded in a water soluble matrix or whole. Those skilled in the art are also fully aware that the present invention further includes embedding the instant dry formulation in a water soluble package such as a pouch, sachet, pouch, capsule, and the like.

The invention further comprises a process for the preparation of a soluble granule (SG) formulation comprising at least one sulfonamide free acid active component, the process comprising: (1) forming at least one sulfonamide free acid active component by formulation, at least A solid base, a powdered ingredient of at least one or more additives; (2) adding water to the furnish; (3) extruding the wet ingredients through a die to form granules; (4) drying the granules to remove water.

The invention also provides a method for administering a soluble granule, which comprises: (1) distributing a sulfonamide active group into a soluble granule; (2) mixing the soluble granule with water to obtain a clear and transparent diluent (3) Applying the pesticide/water mixture.

The invention also relates to a pesticide/water mixture prepared by such a process.

The dry formulation can be administered by methods well known in the art. These methods include spraying, spraying, dripping, dipping, injecting, irrigating, and the like.

The pesticidal composition of the present invention is usually spread after being diluted with water. Technology in the technical field The skilled person will find that when diluted with water, the dilution factor of the pesticide composition depends on the type of pesticide, the type of harmful organism to be controlled, the type of crop to be treated, the type of bacteria to be alleviated, the type of weed to be controlled, the treatment period, and the application method. It varies and is not given, but is usually in the range of 20-10,000 times.

Example 1: 6% nicosulfuron SG

Nicosulfuron

6%

Supralate ® (sodium lauryl sulfate, Wito Inc., Greenwich)

0.5%

Reax ® 88B (sodium lignosulfonate, Westvaco Corp)

5%

Sodium carbonate (Na ₂ CO3)

1%

Potassium sulfate (K ₂ SO ₄ )

47.5%

lactose

40%

Example 2 1% nicosulfuron SG

Nicosulfuron

1%

Supralate ® (sodium lauryl sulfate, Wito Inc., Greenwich)

0.5%

Reax ® 88B (sodium lignosulfonate, Westvaco Corp)

2.5%

Sodium carbonate (Na ₂ CO3)

1%

Sodium acetate (NaAC)

89%

Example 3 90% nicosulfuron SG

Nicosulfuron 90%

Supralate ○R (sodium lauryl sulfate, Wito Inc., Greenwich) 0.5%

Reax ○R88B (sodium lignosulfonate, Westvaco Corp) 5%

Sodium bicarbonate (NaHCO3) 1%

Example 4 15% Nicosulfuron SG

Nicosulfuron 15%

Supralata ○ R (sodium lauryl sulfate, Wito Inc., Greenwich) 0.5%

Reax ○R88B (sodium lignosulfonate, Westvaco Corp) 5%

Sodium carbonate monohydrate (Na2CO3.H20) 20%

Sugar 50.5%

Example 5 15% Nicosulfuron SG

Nicosulfuron 15%

Supralate ○R (sodium lauryl sulfate, Wito Inc., Greenwich) 0.5%

Reax ○R88B (sodium lignosulfonate, Westvaco Corp) 5%

Sodium hydrogen phosphate (NaHPO4) 19.5%

Example 6 10% pyrazosulfuron SG

Pyrazosulfuron 10%

Supralate ○R (sodium lauryl sulfate, Wito Inc., Greenwich) 0.5%

Reax ○R88B (sodium lignosulfonate, Westvaco Corp) 5%

Potassium carbonate (K2CO3) 10%

Lactose 44.5%

Example 7 2% bensulfuron SG

Bensulfuron 2%

Supralate ○R (sodium lauryl sulfate, Wito Inc., Greenwich) 0.5%

Reax ○R88B (sodium lignosulfonate, Westvaco Corp) 5%

Sodium bicarbonate (NaHCO3) 40%

Sucrose 4.5%

Example 8 40% Aminsulfuron SG

Amphetsulfuron 40%

Supralate ○R (sodium lauryl sulfate, Wito Inc., Greenwich) 0.5%

Reax ○R88B (sodium lignosulfonate, Westvaco Corp) 5%

Sodium bicarbonate (NaHCO3) 2%

Lactose 48.5%

Example 9 1% bensulfuron SG

Bensulfuron 1%

Supralate ○R (sodium lauryl sulfate, Wito Inc., Greenwich) 0.5%

Reax ○R88B (sodium lignosulfonate, Westvaco Corp) 5%

Sodium tripolyphosphate (Na5P3O10) 10%

Lactose 34.5%

Example 10 50% bensulfuron SG

Bensulfuron 50%

Supralate ○R (sodium lauryl sulfate, Wito Inc., Greenwich) 0.5%

Reax ○R88B (sodium lignosulfonate, Westvaco Corp) 5%

Potassium carbonate 1%

Lactose 38.5%

Example 11 1% metsulfuron SG

Methsulfuron 1%

Supralate ○R (sodium lauryl sulfate, Wito Inc., Greenwich) 0.5%

Reax ○R88B (sodium lignosulfonate, Westvaco Corp) 5%

Sodium tripolyphosphate (Na5P3O10) 50%

Lactose 25.5%

Example 12 50% bensulfuron-methyl SG

Bensulfuron 50%

Supralate ○R (sodium lauryl sulfate, Wito Inc., Greenwich) 0.5%

Reax ○R88B (sodium lignosulfonate, Westvaco Corp) 5%

Potassium phosphate (K3PO4) 1%

Sucrose 33.5%

Example 13 10% penoxsulam SG

Penoxsulam 10%

Supralate ○R (sodium lauryl sulfate, Wito Inc., Greenwich) 0.5%

Reax ○R88B (sodium lignosulfonate, Westvaco Corp) 5%

Potassium hydrogen phosphate (K2HPO4) 1%

Sucrose 23.5%

Example 14 5% imipensulfuron SG

Nicosulfuron 5%

Supralate ○R (sodium lauryl sulfate, Wito Inc., Greenwich) 0.5%

Reax ○R88B (sodium lignosulfonate, Westvaco Corp) 4.5%

Sodium bicarbonate (NaHCO3) 50%

Example 15 5% sulfometuron SG

Sulfasulfuron 5%

Supralate ○R (sodium lauryl sulfate, Wito Inc., Greenwich) 0.5%

Reax ○R88B (sodium lignosulfonate, Westvaco Corp) 4.5%

Hydrated sodium carbonate (NaCO3 H2O) 1%

Lactose 29%

Example 16 5% thiophenesulfuron SG

Thiosulfuron 5%

Supralate ○R (sodium lauryl sulfate, Wito Inc., Greenwich) 0.5%

Reax ○R88B (sodium lignosulfonate, Westvaco Corp) 4.5%

Ammonium hydrogen phosphate ((NH)2HPO4) 25%

Lactose 25%

Example 17 10% methyl disulfuron SG

Methyl disulfuron 10%

Supralate ○R (sodium lauryl sulfate, Wito Inc., Greenwich) 0.5%

Reax ○R88B (sodium lignosulfonate, Westvaco Corp) 4.5%

Sodium citrate (Na2SiO3) 10%

Sucrose 55%

Example 18 1.5% acesulfamesulfur SG

Acetazosulfuron 1.5%

Supralate ○R (sodium lauryl sulfate, Wito Inc., Greenwich) 0.5%

Reax ○R88B (sodium lignosulfonate, Westvaco Corp) 4.5%

Sodium tripolyphosphate (Na5P3O10) 3%

Lactose 61.3%

Example 19 20% tetrazincsulfuron SG

Tebuminsulfuron 20%

Supralate ○R (sodium lauryl sulfate, Wito Inc., Greenwich) 0.5%

Reax ○R88B (sodium lignosulfonate, Westvaco Corp) 4.5%

Sodium tridecanoate (Na2Si3O7) 5%

Sucrose 30%

Example 20 30% chlorsulfuron SG

Chlorsulfuron-methyl 30%

Supralate ○R (sodium lauryl sulfate, Wito Inc., Greenwich) 0.5%

Reax ○R88B (sodium lignosulfonate, Westvaco Corp) 4.5%

Sodium polyphosphate (NaPO3) n 20%

Lactose 15%

Example 21 60% trifluorosulfuron SG

Trifluorosulfuron 60%

Supralate ○R (sodium lauryl sulfate, Wito Inc., Greenwich) 0.5%

Reax ○R88B (sodium lignosulfonate, Westvaco Corp) 4.5%

Sodium hexametaphosphate (NaP03) 6 15%

Example 22 70% chlorsulfuron SG

Chlorsulfuron 70%

Supralate ○R (sodium lauryl sulfate, Wito Inc., Greenwich) 0.5%

Reax ○R88B (sodium lignosulfonate, Westvaco Corp) 4.5%

Sodium citrate (Na2SiP03) 6 15%

Comparative example

In Comparative Example AV corresponding to each of Examples 1-22, a solid base was not used. The amount of the solid base in Example 1-22 was replaced with a water-soluble filler, and the others were unchanged.

Laboratory cleaning test steps

The test was carried out by dispersing the samples of Examples 1-22 and the samples of Comparative Example AV, respectively, in a dilution obtained in water. A sample of the same quality was separately added to tap water (300 ml) in a 400 ml biscuit and magnetically stirred for 2 minutes. The resulting dilution was loaded into three 4 ounce (118 ml) polyethylene vials in 100 ml aliquots. The bottle was sealed, turned twice and placed overnight. After standing overnight, the bottles were inverted twice and the liquid contents were poured out. Tap water (10 ml) was added and the bottle was inverted until all the precipitate was resuspended in water, and the contents were poured out. Tap water (10 ml) was added and the bottle was inverted twice and allowed to stand for 10 minutes. The bottle was inverted 2 times and the contents were poured out. Acetonitrile (10 ml) was added to the bottle to extract the residual material. The acetonitrile solution was analyzed by reverse phase liquid chromatography with a UV detector. The cleaning solution (concentration of the sulfonamide herbicide in acetonitrile solution) is reported in ppm in the table below. A low cleaning rate indicates a more efficient cleaning than a high cleaning rate. Repeat the wash test twice for the comparative example AV without the base formulation and list the results twice

As can be seen from the cleaning rate data of the above table, the addition of the solid base in the herbicidal composition of the 1-22 sulfonamide free acid according to the present invention significantly reduces the residue of the sulfonamide in the bottle. Comparative Example AV shows that in the herbicidal composition containing the sulfonamide free acid, when the content of the sulfonamide exceeds 10%, the residue of the sulfonamide in the bottle after the rinsing is severe.

Bioassay program:

The test was carried out by dispersing a sample of the same quality of Example 1-22 and a sample of Comparative Example AV in water to obtain a diluted solution. The resulting dilution was loaded into three 4 ounce (118 ml) polyethylene vials in 100 ml aliquots. The bottle was sealed, turned twice and placed overnight. After standing overnight, the bottles were inverted twice and the liquid contents were poured out. Tap water (10 ml) was added and the bottle was inverted until all the precipitate was resuspended in water, and the contents were poured out. Add tap water (10ml) and turn the bottle twice, then quiet Set for 10 minutes. The bottle was inverted 2 times and the contents were poured out. In the above washing step, acetonitrile (10 ml) was added to the bottle to extract a residual substance. The acetonitrile solution was analyzed by reverse phase liquid chromatography with a UV detector. In this biological test step, fresh water is added to the bottle, and the crop (sugar beet) is sprayed with the final rinse solution. The following bioassay protocol was used to determine the percentage of crop injury. The sugar beet seedlings (in the two-leaf stage) were grown in the greenhouse (lighting at 210 C for 14 hours, 10 hours at 170 c without light) and spraying with the last rinse solution described above. Three replicate pots were processed for each sample, and four sugar beets were planted in each dish.

Plants were kept in the greenhouse until identification was carried out 14 to 23 days after treatment. The damage of the treated plants was visually identified on a scale of 0 to 100 (0 = no damage, 100 = complete kill) compared to the control plants. The level of damage is based on various signs of existence, including reduced biomass, impaired growth, reduced development, chlorosis, blemishes, leaf spots and leaf wrinkles or deformation.

As can be seen from the above table, in the herbicidal composition containing sulfonamide according to the embodiment 1-22 of the present invention, the addition of the solid base significantly reduces the residue of the sulfonamide in the spray tank, and finally the rinse liquid The spray solution has almost no damage to the beets. The results of Comparative Examples A-V show that in the herbicidal composition containing sulfonamide, when the content of sulfonamide exceeds 10%, The final rinsed spray completely killed the beets.

Claims (7)

A soluble granule comprising a sulfonamide free acid active ingredient, comprising: (i) 2-90% anhydrous basis weight of an active component comprising at least one sulfonamide herbicide free acid; (ii) 0- 95% anhydrous basis weight of one or more additives selected from the group consisting of wetting agents, dispersing agents, lubricants, anti-caking agents, chemical stabilizers and diluents; (iii) at least one solid organic base selected from the group consisting of sodium acetate The amount of the solid organic base is at least 1% of the pesticide composition, and wherein the weight ratio of the solid organic base to the sulfonamide herbicide free acid is 1:90-90:1; The sum of the base weight percentages is 100%; wherein the soluble granules do not contain at least 50 equivalent % of an inorganic base having a conjugate acid pKa greater than the highest pKa of the sulfonamide free acid by at least 2.1 units. The soluble granule containing the sulfonamide free acid active ingredient according to claim 1, wherein the at least one sulfonamide herbicide free acid is selected from the group consisting of nicosulfuron, tribenuron, metsulfuron, and bensulfuric acid. Sulfurone, penoxsulam, rimsulfuron, sulfometuron, thifensulfuron, methyl disulfuron, pyrazosulfuron, chlorsulfuron, trifluorosulfuron, tetrazinsulfuron, Acetazosulfuron, ethamsulfuron, chlorsulfuron. A soluble granule comprising a sulfonamide free acid active ingredient according to claim 1, wherein the at least one sulfonamide herbicide free acid is sulfometuron. A soluble granule comprising a sulfonamide free acid active ingredient according to claim 1, wherein the at least one sulfonamide herbicide free acid is rimsulfuron. A soluble granule comprising a sulfonamide free acid active ingredient according to claim 1, wherein the at least one sulfonamide herbicide free acid is nicosulfuron. A soluble granule comprising the sulfonamide free acid active ingredient of claim 1, wherein the at least one sulfonamide herbicide free acid is thifensulfuron. A soluble granule comprising the sulfonamide free acid active ingredient according to claim 1, wherein the at least one sulfonamide herbicide free acid is bensulfuron.