JPH058164B2 - - Google Patents

Description

[Detailed description of the invention]

The present invention comprises as an essential ingredient a sulfonylurea or an agriculturally suitable salt thereof together with an effective amount of a salt of a carboxylic acid or an inorganic acid or a mixture of such salts of a carboxylic acid or an inorganic acid; and the solubility of the carboxylic acid or inorganic acid salt is equal to or greater than 3% at a pH of about 6 to 10, and furthermore, the solubility of the carboxylic acid or inorganic acid salt is greater than or equal to 3% at a pH of about 6 to 10; between,
The present invention relates to a stabilized aqueous agricultural composition characterized by the following. Sulfonylureas are known from the literature. For example, U.S. Pat.
No. 4169719 describes herbicidal sulfonylureas. Aqueous suspension compositions of these herbicides are stabilized by the method of the present invention. These and other patents disclose sulfonylureas that are highly effective as herbicides. However, agriculturally suitable compositions of such sulfonylureas require long-term storage after their production. It is extremely important to maintain the stability of herbicide compositions of this type, since unstable compositions are significantly less effective when used. That is, if the effectiveness of the herbicide is to be maximized, the active ingredient must be kept intact in the composition. In accordance with the present invention, the following compositions have been discovered that are useful in maintaining the stability of sulfonylurea herbicides. The present invention comprises a compound of the formula or an agriculturally suitable salt of the formula in an effective amount of diammonium hydrogen phosphate;
Contains as an essential component together with a salt of a carboxylic acid or an inorganic acid selected from ammonium acetate, lithium acetate, sodium thiocyanate, sodium acetate and potassium acetate, or a mixture of such salts of a carboxylic acid or an inorganic acid, and as conditions: 5°C and the solubility of the carboxylic acid or inorganic acid salt at pH 6-10 is equal to or greater than 3%;
A stabilized aqueous suspension composition characterized in that the pH of the 0.1 molar aqueous solution is between 6 and 10. Unless otherwise specified, all sections are material criteria. The concentration of one or more salts of carboxylic or inorganic acids in the composition is between 3% and the saturation limit of that salt in aqueous solution. The meanings of the substituents are as follows. R is

【formula】

【formula】

[Formula], R ₁ is H or CH ₃ , R ₂ is F, Cl, Br, C ₁ to C ₄ alkyl, SO ₂ NR ₆ R ₇ , S(O) _o R ₈ , SO ₂ NCH ₃
(OCH ₃ ), CO ₂ R ₉ , OSO ₂ R ₁₀ , OR ₁₁ , NO ₂ ,

【formula】 【formula】

【formula】 or

[Formula], R ₃ is H, F, Cl, Br, CH ₃ , OCH ₃ or CF ₃ , R ₄ is Cl, NO ₂ or CO ₂ R ₁₀ , R ₅ is Cl, Br, _SO2NR6R7 , S ₍ O) _{oR10 or CO2R10} , _R6 and _R7 are independently _C1 - _{C3 alkyl} , and _R8 is _{C1 - C3} alkyl or F, Cl or Br
_C1 - _C3 alkyl substituted by 1 _to 5 atoms of, and _R9 is _{C1 - C4} alkyl, _{CH2CH2OCH3 , CH2CH2Cl} or _CH2CH = _CH2 , _R10 is _C1 - _C3 alkyl, _R11 is _C1 - _C4 alkyl, _CH2CH = _CH2 , _CH2C≡CH or by 1-5 atoms of F, Cl or Br substituted _C1 - _C3 alkyl, n is 0 or 2, Z is CH or N, X is _CH3 , _OCH3 , Cl or _OCHF2 , Y is _CH3 , _OCH3 , CH(OCH ₃ ) ₂ , OCHF ₂ or

and M ^{+ m} is an agriculturally suitable cation, and m is 1, 2 or 3, provided that when X is Cl, Z is CH and Y is OCH ₃ or OCF ₂ H. Compositions of the invention can include one or more compounds of formula or one or more compounds of formula.
Furthermore, the composition can simultaneously contain compounds of both formula and formula. The compositions of the invention may also optionally contain other herbicides. Preferred for reasons of greater stability and/or more favorable physical properties are: Compounds of formula or compositions of generic embodiments comprising compounds of formula wherein 1 M is ammonium, substituted ammonium or alkali metal ion and the counterion of the salt of carboxylic acid or inorganic acid is ammonium, substituted ammonium or alkali metal ion thing. 2 R is

【formula】

【formula】 or

[Formula], R ₁ is H, R ₂ is Cl, CH ₃ , SO ₂ N(CH ₃ ) ₂ , S(O) _o R ₈ , CO ₂ R ₉ , OSO ₂ R ₁₀ , OR ₁₁ or _NO2 , _R3 is H, Cl, _CH3 , _OCH3 or _CF3 , _R8 is _C1 - _C3 alkyl, _CF3 , _{CF2H or CF2CF2H} , R The composition of preferred embodiment 1, wherein ₉ is _C1 - _C4 alkyl and _R11 is _C1 - _{C4 alkyl} , _CF3 , _CF2H or _CF2CF2H . 3. The composition of preferred embodiment 2, wherein the compound is an agriculturally suitable salt of formula. The composition of preferred embodiment 3, wherein the cation of the compound of formula 4 and the cation of the salt of a carboxylic acid or inorganic acid are the same. 5. The composition of the generic embodiment, wherein the concentration of one or more salts of carboxylic or inorganic acids is greater than or equal to 10% and less than or equal to 40% or the salt saturation limit of the solution. 6. The composition of preferred embodiment 1, wherein the concentration of one or more salts of carboxylic or inorganic acids is greater than or equal to 10% and less than or equal to 40% or the salt saturation limit of the solution. 7. The composition of preferred embodiment 2, wherein the concentration of one or more salts of carboxylic acids or inorganic acids is 10% or more and 40% or less, or the salt saturation limit of the solution. 8. The composition of preferred embodiment 3, wherein the concentration of one or more salts of carboxylic or inorganic acids is greater than or equal to 10% and less than or equal to 40% or the salt saturation limit of the solution. 9. The composition of preferred embodiment 4, wherein the concentration of one or more salts of carboxylic or inorganic acids is greater than or equal to 10% and less than or equal to 40% or the salt saturation limit of the solution. Particularly preferred for reasons of greatest stability and/or greatest availability are: 2-[[(4-chloro-6-methoxypyrimidin-2-yl)aminocarbonyl]-aminosulfonyl]benzoic acid, ethyl ester; 2-[[(4-methoxy-6-methyl-1,3,
5-triazin-2-yl)aminocarbonyl]
-aminosulfonyl]benzoic acid, methyl ester, 2-[[(4-6-dimethylpyrimidin-2-yl)aminocarbonyl]aminosulfonyl]benzoic acid, methyl ester, 2-chloro-N-[(4-methoxy- 6-Methyl-1,3,5-triazin-2-yl)-aminocarbonyl]benzenesulfonamide, 2-[[(4,6-dimethoxypyrimidine-2-
yl)aminocarbonyl]aminosulfonylmethyl]benzoic acid, methyl ester, 3-[[(4-methoxy-6-methyl-1,3,
5-triazin-2-yl)aminocarbonyl]
From the agriculturally suitable salts of aminosulfonyl]-2-thiophenecarboxylic acid methyl ester, N-[(4,6-dimethylpyrimidin-2-yl)aminocarbonyl]-2-hydroxybenzenesulfonamide, ethanesulfonate a composition comprising a compound of the selected formula and a salt of a carboxylic or inorganic acid selected from diammonium hydrogen phosphate, ammonium acetate, lithium acetate, sodium acetate, potassium acetate, or sodium thiocyanate, and This is a composition containing an ammonium salt of 2-chloro-N-[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)aminocarbonyl]benzenesulfonamide and diammonium hydrogen phosphate. The present invention relates to stable and easily dispersible concentrated liquid suspensions of compounds of the formula or agriculturally suitable salts of the formula in aqueous salt solutions. The compounds of the formula are useful herbicides and their preparation is well known in the art. For example, U.S. Patent No. 4127405
No. 4169719. Agriculturally suitable salts of the formula are also useful herbicides and can be prepared by many methods known in the art. For example, a metal salt can be used to combine a compound of formula with an alkali metal salt with a sufficiently basic anion (e.g.
hydroxides, alkoxides, carbonates, or hydrides). Ammonium salts and substituted ammonium salts can be made by similar methods. Salts of the formula can also be prepared by exchanging one cation for another.
Cation exchange can be carried out by directly treating an aqueous solution of a salt of the formula (eg an alkali metal or ammonium salt) with a solution containing the cation to be exchanged. This method is most effective when the desired salt containing the exchanged cation is insoluble in water and can be separated by filtration. Ion exchange can also be carried out by passing an aqueous solution of a salt of the formula (eg, an alkali metal salt or an ammonium salt) through a column packed with a cation exchange resin containing the cations to be exchanged.
In this method, the resin cations are exchanged with the original salt cations and the desired product is eluted from the column. This method is particularly useful when the desired salt is water soluble. Liquid concentrates are desirable because they can be easily metered, poured, handled, or diluted in preparing aqueous slurries for spraying. Some of the compounds of formula and salts of formula do not have high solubility in water or other inexpensive solvents, and even more are not chemically stable over long periods of time in these solvents. When dissolved in water alone, partial or complete hydrolysis and/or crystal growth may occur during storage and it may not be possible to form a stable solution or suspension. In the present invention, the aqueous suspending medium comprises an ammonium, substituted ammonium or alkali metal salt of a carboxylic or inorganic acid or a mixture of such salts, with the proviso that the solubility of those salts at pH 6-10 is at 5°C. 3% and further the pH of the 0.1 molar aqueous solution of the carboxylic acid salt or inorganic acid salt is between 6 and 10. It has been found that suspensions can be produced. The stabilization achieved with these compositions is evident in several respects. Firstly, the chemical stability of compounds of formula or salts of formula in aqueous suspensions is significantly improved, allowing the production of such suspensions that are relatively stable during storage. Second, crystal growth of the active ingredient is reduced and a controlled degree of aggregation is imparted to the active herbicide particles, which prevents the formation of a cake that is difficult to resuspend during storage.
Third, the density of the suspending medium can be up to 30% higher than that of water, which reduces the tendency of suspended particles to settle. Fourth, the dissolved salt maintains the fluidity of the composition at temperatures of -6°C and below. A further advantage of these compositions is that, although the compounds of formula and the salts of formula are relatively insoluble in the suspending medium, when diluted with water in a spray tank, they reduce the pH of the spray solution. If it is about 7.0 or higher, it will dissolve quickly and completely at more dilute spray concentrations. Preferred salts in aqueous media are ammonium, substituted ammonium or alkali metal salts of carboxylic or inorganic acids having a solubility in water of 3% or more at 5°C. A useful concentration range is from 3% to saturation point at 5°C. Preferred salts of the invention further have a PH between 6 and 10 in 0.1 molar aqueous solution. Examples of these salts are diammonium hydrogen phosphate, ammonium acetate, lithium acetate, ammonium thiocyanate, sodium acetate, potassium acetate or miscible mixtures thereof. Diammonium hydrogen phosphate and sodium acetate are preferred for compositions containing the ammonium and sodium salts, respectively, of the salts of formula.
The useful PH range of these compositions is 6-10;
7 to 9 are preferred. In most cases, the above salts will automatically produce a composition with the desired PH. The anion of a salt of a carboxylic acid or an inorganic acid can act as an acid acceptor and form a salt of the formula from the corresponding covalent acid in situ.
Utilizing this principle, it is possible to directly produce a salt composition of the formula from the coylic acid of the formula. If a higher or lower PH is desired, small amounts of acids or bases can be added to the composition. For example, in the case of diammonium hydrogen phosphate, the pH can be lowered by adding phosphoric acid or ammonium dihydrogen phosphate. PH can be raised using ammonium hydroxide. The base or acid can have the same anion or cation as the salt, but this is not a requirement. The composition of the invention comprises a compound of the formula or a salt of the formula suspended in an aqueous solution containing an amount of from 3% to salt saturation of an agriculturally suitable salt of a carboxylic or inorganic acid, or a mixture thereof, as described above. Approximately 1 to 50%
(preferably 10 to 40%). Preferred concentrations of these carboxylic or inorganic acid salts range from about 10 to 40% in the aqueous phase. The composition can also contain about 0.1 to 20% surfactant. A relatively high ratio of surfactant to active ingredient is sometimes desirable and can be achieved by incorporation into the composition or tank mixing. Surfactants used in this composition include trimethylnonyl polyethylene glycol ether,
Common wetting and dispersing agents such as sodium alkylnaphthalene sulfonate, sodium alkylbenzene sulfonate, sodium dioctyl sulfosuccinate, sodium dodecyl sulfate, ammonium and sodium salts of lignosulfonic acid, and formaldehyde condensates of naphthalene sulfonic acid. More specific examples are sodium lignosulfonate and ammonium lignosulfonate. Optionally, the composition can also contain about 0.01 to 5.0% thickeners or suspending agents such as carboxymethyl cellulose, polysaccharide gums, natural and purified smectite-type clays, and synthetic silica. The compositions of the invention can include compounds of more than one formula or compounds of more than one formula.
Furthermore, the composition can simultaneously contain compounds of both formula and formula. The compositions of the invention may also optionally contain other herbicides. The herbicides listed below are examples of substances that may be particularly useful in such combinations.

【table】

[Table] Cacodylic acid Hydroxydimethyl arsenic acid
(cacodylic acid) compound

[Table] Ajin

【table】

[Table] Oxyacetic acid

【table】

[Table] Nzamide

【table】

Table: Chilurea If the herbicide added is water-soluble, it may be necessary to adjust the PH of the resulting composition to be within the range of 6-10. Furthermore, water-soluble herbicides may act to replace some or all of the stabilizing inorganic and/or carboxylic acid salts. The method of making the stabilized compositions of the present invention is well known and includes air milling in combination with high speed compounding;
There are colloid mills, sand mills, bead mills and ball mills. A preferred method of preparing a stabilized composition of the formula is to suspend the compound of the formula in water containing a surfactant and a thickener or suspending agent, followed by the addition of a desired base such as ammonium hydroxide or sodium hydroxide. It involves neutralizing the pH to 6.0 to 10.0, preferably 7.0 to 9.0, and then adding a solid insolubilizing salt to form a composition while stirring. The method of adding the insolubilizer salt is important. It is best to add the salt to the neutralized co-yellow acid in small portions so that the precipitate forms more slowly, otherwise sticky solids or gums may form. Next, the resulting suspension is ground in a colloid mill or bead mill to give 1
Particle size is ~20 microns, preferably 2-8 microns. The stable aqueous suspension obtained is suitable for use in herbicide applications. Example 1 2-chloro-N-[(4-methoxy-6-methyl-
1,3,5-triazin-2-yl)-aminocarbonyl]benzenesulfonamide
34.20% Sodium alkylnaphthalene sulfonate 2.00% Polysaccharide thickener 0.05% Magnesium aluminum silicate thickener
0.20% diammonium hydrogen phosphate 16.05% ammonium hydroxide solution (29% NH ₃ ) 5.60% water and impurities balance Sodium alkylnaphthalene sulfonate was dissolved in water with stirring and the sulfonamide was added little by little and well dispersed. Ammonium hydroxide was added to the dispersion to form the sulfonamide salt. As a result, the pH was 7.5. While adding diammonium hydrogen phosphate and dissolving (28.5 of the solution
%) and continued stirring. The polysaccharide and silicate thickener were added and the resulting mixture was sand milled to produce particles essentially 5 microns in size or less. The pH of this composition was 7.8. As a result of accelerated aging at 45℃ for 3 weeks,
The composition did not settle to any significant extent and the suspended solids remained soft. All compositions could be easily fluidized by stirring or shaking.
No detectable decomposition of the active ingredient occurred, whereas an equivalent composition without diammonium hydrogen phosphate showed a relative decomposition rate of 6% under the same conditions. Example 2 The following composition illustrates a method for producing in situ a composition of a salt of the formula from a compound of the formula. 2-chloro-N-[(4-methoxy-6-methyl-
1,3,5-Triazin-2-yl)-aminocarbonyl]benzenesulfonamide 33.9% Sodium ligninsulfonate 2.0% 37.5% diammonium hydrogen phosphate solution 64.1% Sodium ligninsulfonate and sulfonamide were stirred into the phosphate solution. Added some. The mixture was then sand milled to essentially 5 micron or less particles. The pH of this composition was 8.25. The sample aged for two weeks at 45°C showed a relative degradation of the active ingredient of 0.47%, while the phosphate-free composition showed a relative degradation of the same ingredient of 6.0%.
The stabilized and aged composition did not exhibit significant settling and was easily fluidized by stirring. Example 3 Ammonium salt of sulfonylurea, 2-[[(4
-chloro-6-methoxypyrimidin-2-yl)
A stable suspension of -aminocarbonyl]aminosulfonyl]benzoic acid, ethyl ester was prepared as described in Example 2 using the same percentages of ingredients. The PH of the composition was 7.95. The sample aged for 2 weeks at 45°C showed a relative degradation of active ingredient of 0.4%, while the phosphate-free composition showed a relative degradation of 4.0%.
% relative decomposition rate of the same component is shown. The aged composition had little sedimentation and was easily fluidized by stirring. Example 4 2-[[(4-methoxy-6-methyl-1,3,5
-triazin-2-yl)-aminocarbonyl]
Aminosulfonylbenzoic acid 21.3% Sodium ligninsulfonate 1.11% Sodium hydroxide (50%) 4.48% Sodium acetate 18.71% Polysaccharide thickener 0.05% Water and impurities Balance While stirring, add sodium ligninsulfonate and sodium hydroxide. Dissolved in water and added the sulfonylurea in portions and reacted to form the aqueous sodium salt. To this solution was added 1/4 of the sodium acetate and after 5 minutes another 1/4. The remainder of the sodium acetate was added after approximately 15 minutes when rapid precipitation of the sulfonylurea salt was observed to occur. The percentage of sodium acetate in the aqueous phase was 25.0. Sandwich the resulting composition.
Milling produced particles with a particle size of essentially 5 microns or less. The polysaccharide thickener was added a few minutes before completing the milling operation. The PH of the composition was 9.03. After aging for 3 weeks at 45°C, the suspended solids did not settle and the composition could be easily fluidized by shaking. No detectable decomposition of the active ingredient occurred, whereas the composition without added acetic acid showed a 30% decomposition rate during the same accelerated aging period. In the following examples, stable suspensions of sulfonylureas were prepared by the method described in Example 4 using the following salts as stabilizers to suppress chemical decomposition and prevent crystal growth.

[Table] Example 8 3-[[(4-methoxy-6-methyl-1,3,5
-triazin-2-yl)aminocarbonyl]aminosulfonyl]-2-thiophenecarboxylic acid,
Methyl ester 12.0% Sodium alkylnaphthalene sulfonate 2.4% Lithium hydroxide- _H2O 1.3% Lithium acetate 29.2% Water and impurities Balance A stable suspension of the lithium salt of a sulfonylurea was prepared by the method described in Example 4. did. The lithium acetate concentration in the aqueous phase was 35%. The PH of the composition is
It was 7.9. Samples aged for 3 weeks at 45°C showed no loss of active ingredient, whereas the loss of the same ingredient from a composition without lithium acetate aged in the same manner was over 20%. Example 9 The ammonium salt of the sulfonamide of Example 1 is air milled to obtain a product with a particle size of essentially 5 microns or less, and then added with thorough agitation into a mixture of the remaining ingredients of the composition of Example 1. Dispersed. Suspension behavior and chemical stability were essentially as described in Example 1.

Claims (1)

[Scope of Claims] 1. Agriculturally suitable salts of carboxylic acids or inorganic acids selected from diammonium hydrogen phosphate, ammonium acetate, lithium acetate, sodium thiocyanate, sodium acetate, and potassium acetate, or carboxylic acid salts of such kinds. A mixture of inorganic acid salts, provided that the solubility of the carboxylic or inorganic acid salt at 5° C. and pH 6 to 10 is equal to or greater than 3%, and furthermore, a 0.1 molar solution of the carboxylic or inorganic acid salt is PH is between 6 and 10, and the following formula R is [Formula] [Formula] [Formula], R ₁ is H or CH ₃ , R ₂ is F, Cl, Br, C ₁ to _{C 4} alkyl, SO ₂ NR ₆ R ₇ , S(O ) nR ₈ , SO ₂ NCH ₃ (OCH ₃ ),
CO ₂ R ₉ , OSO ₂ R ₁₀ , OR ₁₁ , NO ₂ , [Formula] [Formula] [Formula] or [Formula], and R ₃ is H, F, Cl, Br, CH ₃ , OCH ₃ or CF ₃ , R ₄ is Cl, NO ₂ or CO ₂ R ₁₀ , R ₅ is Cl, Br, SO ₂ NR ₆ R ₇ , S(O)n R ₁₀ or CO ₂ R ₁₀ , R ₆ and R ₇ is independently C ₁ -C ₃ alkyl and R ₈ is C ₁ -C ₃ alkyl or C ₁ -C ₃ alkyl substituted by 1 to 5 atoms of F, Cl or Br. , R ₉ is C ₁ -C ₄ alkyl, CH ₂ CH ₂ OCH ₃ , CH ₂ CH ₂ Cl or CH ₂ CH=CH ₂ , R ₁₀ is C ₁ -C ₃ alkyl, and R ₁₁ is _C1 - _C4 alkyl, _CH2CH = _CH2 , _CH2C≡CH or F, Cl or Br
_C1 - _C3 alkyl substituted by 1 to 5 atoms of, n is 0 or 2, Z is CH or N, and X is _CH3 , _OCH3 , Cl or _OCHF2 , Y is CH ₃ , OCH ₃ , CH(OCH ₃ ) ₂ , OCHF ₂ or [Formula], and M ^{+ m} is an agriculturally suitable cation, and m is 1, 2 or 3; , However, when X is Cl, Z is CH and Y is OCH ₃ or OCF ₂ H, consisting essentially of one or more compounds selected from the above carboxylate or A stabilized aqueous agricultural composition characterized in that the concentration of the inorganic acid salt is between 3% and the saturation limit of that salt in aqueous solution. 2. If the counterion of the carboxylate or inorganic acid salt is ammonium, substituted ammonium or alkali metal ion, and the compound is a salt of formula, then M is likewise ammonium, substituted ammonium or alkali metal ion, the claim The composition according to item 1. 3 R is [Formula] [Formula] or [Formula], R ₁ is H, and R ₂ is Cl, CH ₃ , SO ₂ N(CH ₃ ) ₂ , S(O)nR ₈ , CO ₂ R ₉ , _OSO2R10 , _OR11 or _NO2 , _R3 is H, Cl, _CH3 , _OCH3 or _CF3 , _R8 is _C1 - _{C3 alkyl} , _CF3 , _CF2H or CF _2
CF2H , _R9 is _C1 - _C4 alkyl, and _R11 is _C1 - _C4 alkyl, _CF3 , _CF2H or _CF2
The composition according to claim 2, which is CF ₂ H. 4. A composition according to claim 3, wherein the compound is an agriculturally suitable salt of the formula. 5. The composition according to claim 4, wherein the cation of the compound of formula 5 and the cation of the carboxylate or inorganic acid salt are the same. 6. The composition according to claim 1, wherein the concentration of the carboxylic acid salt or inorganic acid salt is 10% or more and 40% or less, or the salt saturation limit of the solution. 7. The composition according to claim 2, wherein the concentration of the carboxylic acid salt or inorganic acid salt is 10% or more and 40% or less or the salt saturation limit of the solution. 8. The composition according to claim 3, wherein the concentration of the carboxylic acid salt or inorganic acid salt is 10% or more and 40% or less or the salt saturation limit of the solution. 9. The composition according to claim 4, wherein the concentration of the carboxylic acid salt or inorganic acid salt is 10% or more and 40% or less or the salt saturation limit of the solution. 10 Concentration of carboxylate or inorganic acid salt is 10%
6. The composition according to claim 5, wherein the composition is 40% or less or the salt saturation limit of the solution. 11 Patent claim containing ammonium salt of 2-chloro-N-[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)-aminocarbonyl]benzenesulfonamide with diammonium hydrogen phosphate The composition according to item 1. 12 The compound of formula 2-[[(4-chloro-6-
Claim 1 is an agriculturally suitable salt of methoxypyrimidin-2-yl)aminocarbonyl]aminosulfonyl]benzoic acid, ethyl ester.
Compositions as described in Section. 13 The compound of formula 2-[[(4-methoxy-6
-methyl-1,3,5-triazin-2-yl)
A composition according to claim 1, which is an agriculturally suitable salt of aminocarbonyl]aminosulfonyl]benzoic acid, methyl ester. 14 The compound of formula N-[(4,6-dimethylpyrimidin-2-yl)aminocarbonyl]-2-
A composition according to claim 1, which is an agriculturally suitable salt of hydroxybenzenesulfonamide, ethanesulfonate. 15 The compound of formula 3-[[(4-methoxy-6
-methyl-1,3,5-triazin-2-yl)
-aminocarbonyl]aminosulfonyl]-2-
A composition according to claim 1, which is an agriculturally suitable salt of thiophenecarboxylic acid, methyl ester. Claim 1, wherein the compound of formula 16 is an agriculturally suitable salt of 2-[[(4,6-dimethylpyrimidin-2-yl)aminocarbonyl]-aminosulfonyl]benzoic acid, methyl ester. Composition of. 17 The compound of formula 2-chloro-N-[(4-methoxy-6-methyl-1,3,5-triazine-
The composition of claim 1 which is an agriculturally suitable salt of 2-yl)-aminocarbonyl]benzenesulfonamide. 18 The compound of formula 2-[[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-
2. A composition according to claim 1, which is an agriculturally suitable salt of aminosulfonylmethyl]benzoic acid, methyl ester.