CA2002474A1 - Solid herbicidal preparations - Google Patents
Solid herbicidal preparationsInfo
- Publication number
- CA2002474A1 CA2002474A1 CA002002474A CA2002474A CA2002474A1 CA 2002474 A1 CA2002474 A1 CA 2002474A1 CA 002002474 A CA002002474 A CA 002002474A CA 2002474 A CA2002474 A CA 2002474A CA 2002474 A1 CA2002474 A1 CA 2002474A1
- Authority
- CA
- Canada
- Prior art keywords
- salt
- sodium
- acid
- bromoxynil
- alkali metal
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
Links
Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/36—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids
- A01N37/38—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids having at least one oxygen or sulfur atom attached to an aromatic ring system
- A01N37/40—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids having at least one oxygen or sulfur atom attached to an aromatic ring system having at least one carboxylic group or a thio analogue, or a derivative thereof, and one oxygen or sulfur atom attached to the same aromatic ring system
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
5-17297/1+2/+/MA 1947 Solid Herbicidal Preparations Abstract of the Disclosure The present invention provides a composition comprising ionoxynil and/or bromoxynil in their phenolic form, together with an alkali metal salt of a weak acid.
Description
200Z4~4 5-17297/1+2/+/MA 1947 Solid Herbicidal Preparations The present invention relates to Granular herbicidalcompo-sitions of hydroxy benzonitriles (HBN's) namely Ioxyniland Bromoxynil.
These two active ingredients are normally prepared as esters for Emulsifiable Concentrates (EC's) and as alkali metal salts for other liquid formulations. The liquidformula-tions, especially EC's containing esters, are toxiconskin contact.
The HBN salts are soluble in water and this facilitates dispersion of the formulation in aqueous systems. However, these HBN salts, when processed as a dry powder are extremely irritating to eye, nose and throat. Bearing this in mind, the products are difficult to handle and also have theun-desirable property of being very difficult to dry andthere-forecannot be formulated easily with other watersensitive activeingredients.
The HBN's in their phenol form do not have the sameirritancy or drying problems associated with their salt counterparts.
Unfortunately, they are insoluble in water andcannoteasily be formulated as soluble powders or granules.
The present invention overcomes this problem by formulating the phenolic form of the HBN's with an alkali metal salt which, on addition to water, causes an in situ neutralisation to occur, forming the soluble salts of the HBN's.
Z0024~4 Accordingly, the present invention provides a composition comprising ioxynil and/or bromoxynil in their phenolic form, together with an amount of an alkali metal salt of a weak acidwhich is preferably that which is stoichiometrically requiredto react with the ioxynil and/or bromoxynil phenol, in orderto form a water-soluble salt thereof.
By weak acid is meant an organic or an inorganic acid with dissociation contant Ka between 10-8 and 10-3.
Sodium and potassium ions are preferred as alkali metal kations.
Suitable salts of weak acids are, for example, acetates, carbonates, hydrogencarbonates, hydrogenphosphites, di-hydrogenphosphates, hydrogenphosphates, nitrites, hydrogen-sulphites and polycarboxylates such as malonates.
Preferred alkali metal salts of weak acids are sodium-carbonate, potassiumcarbonate, sodium acetate, sodium malonate and sodium hydrogenphosphite. A very particularly preferred alkali metal salt of a weak acid is sodium carbonate.
Simple phenolic formulations can be prepared which contain sodium or potassium salts of weak acids. These active ingredients when added to the spray tank will dissolve, leaving solutions of spray liquor. The benefits of using these types of solid formulations are:
The less irritant and less moisture sensitive HBN phenols can be used in the preparation.
The formulations in their solid form are very simple in their composition and can be prepared with or without the use of 200Z4~4 wetting or dispersing aids. The formulations can contain water-soluble carriers or fillers.
Compositions according to the present invention also maycon-tain minor amounts of anionic surfactants. Suitableanionic surfactants are polymer- or copolymer-moleculescontaining hydrophilic groups which are capable of forminganions, for example, polymer- or copolymer-moleculescontaining carboxyl groups, sulfuric acid ester groups, sulphonic acid groups or phosphoric acid ester groups.Preferred polymer-molecules are polyacrylates, alkali metal salts ofdiisobutylene maleicacid copolymers, ligninsulphonates andcondensed alkyl arylsulpho-nates. A particularly preferredanionic surfactant isthe sodium salt of diisobutylene maleicacid copolymer.
Suitable groups of water-soluble carriers or fillers may be organicandinorganic salts, ureas and sugars. Preferred water-soluble carriers or fillers are ureas and inorganic salts.Particularlypreferred water soluble carriers or fillers are inorganicsalts, forexample sodium sulphate, potassium sulphate, sodium chloride, potassium chloride, sodium nitrate, potassium nitrate and calcium nitrate but in particularsodium sulphate.
The fact that the active ingredients and in many cases the formulation dissolves in the spray tank gives rise to a non sedimenting spray liquor which can be successfully sprayed over an extended period of time.
Because of the solubility of the formulations, fine grinding of active ingredients is unnecessary.
Another method of exploiting these formulations is that they can be granulated to reduce the level of dust which is generally considered as an undesirable property.
20024~4 Granulation of these formulations can be effected using techniques such as compaction, extrusion, agglomeration or spray drying. Compaction granulation involves compressing dry powder components to form solid sheets which aresub-sequently broken down into granules, using a suitable crusher. Extrusion granulation comprises pressing a paste or wetted powderofthe formulation through a screen; the material extruded isthendried and broken down to granules of a convenient size.Agglomeration granulation comprises spraying a liquid, whichis usually aqueous, into a fluidized powder. The powder agglomerates, form larger particles which are subsequentlydried.
Spray drying granulation involves preparing a solution or suspensionof the formulation, and spraying the solution or suspension down a hot column of air. The droplets arethereby dried to form spherical granules. In the case ofspray drying, reaction will occur between the HBN phenol andthe salt of the weak acid during the preparation of thesolution or slurry. Consequently, HBN salt will be formed, therefore, during this granulation technique. Salt formationmay also occur, to some extent, during extrusion oragglomeration granulation procedures, when quantities ofaqueous medium are added prior to, and during granulationrespectively. No detrimental effect is observed on thequality of theformula-tion.
Another aspect of the formulation of the present invention is the fact that the HBN components can be mixed with other soluble active ingredients such as soluble salts ofchloro-phenoxyalkanoic acids i.e. Mecoprop or sulphonylurease.g.
Triasulfuron. In the case of Triasulfuron, which is apotent herbicide, the solubility increases with increasing pH. It is insoluble at pH 2.5 but has a solubility of 1.5 g/1 at pH7. However, in view of the hydrolysis of Triasulfuron at low pH-values, pH 5-6representsanoptimum.
200Z4'74 The granules produced in these cases still have the same property of being fully dispersible and soluble once stirred into the spray liquor.
The following Examples further illustrate the present invention.
Examples l to 3: Compositions comprising ioxynil and bromoxynil in their phenol form as well as a salt of a weak acid are formulated and have the compositions as set out in Table I.
Table I
Component % w~w % w~w% w/w Ioxynil as phenol 30 30 30 Bromoxynil as phenol 30 30 30 Sodium Carbonate 15 20 to 100%
Sodium Sulphate to 100 % to 100 %
Sodium salt of maleic acid diisobutylen copolymer 0 - 2 0 - 2 0 - 2 The powdered components are homogenised and then granulated by one of the previously mentioned techniques. The result is water soluble granules that eventually dissolve in the spray liquor.
Example 4: A formulation similar to that of Examples 1 to 3, but containing Mecoprop in salt form, is made up and has the composition set out in Table II.
Table II
Component % w/w Ioxynil as phenol 5.0 Bromoxynil as phenol 5.0 Mecoprop asTriethanolamine salt 46.5 Sodium salt of maleic acid diiso-butylene copolymer 2.0 Sodium Carbonate 1.0 Sodium Sulphate to 100 %
The powdered components may be homogenised ln a suitable blender then granulated by first compacting then sieving to a desirable particle size.
Example 5: The formulation defined in Table III is made up:
Table III
Component % w/w Triasulfuron 0.25 Ioxynil as phenol 5.0 Bromoxynil as phenol 5.0 Mecoprop as magnesium salt or Triethanolamine salt 46.75 Sodium salt of maleic acid diisobutylene copolymer 1.0 Sodium Carbonate 1.0 Sodium Sulphate to 100 %
The formulation is granulated using the technique described in Example 4.
These two active ingredients are normally prepared as esters for Emulsifiable Concentrates (EC's) and as alkali metal salts for other liquid formulations. The liquidformula-tions, especially EC's containing esters, are toxiconskin contact.
The HBN salts are soluble in water and this facilitates dispersion of the formulation in aqueous systems. However, these HBN salts, when processed as a dry powder are extremely irritating to eye, nose and throat. Bearing this in mind, the products are difficult to handle and also have theun-desirable property of being very difficult to dry andthere-forecannot be formulated easily with other watersensitive activeingredients.
The HBN's in their phenol form do not have the sameirritancy or drying problems associated with their salt counterparts.
Unfortunately, they are insoluble in water andcannoteasily be formulated as soluble powders or granules.
The present invention overcomes this problem by formulating the phenolic form of the HBN's with an alkali metal salt which, on addition to water, causes an in situ neutralisation to occur, forming the soluble salts of the HBN's.
Z0024~4 Accordingly, the present invention provides a composition comprising ioxynil and/or bromoxynil in their phenolic form, together with an amount of an alkali metal salt of a weak acidwhich is preferably that which is stoichiometrically requiredto react with the ioxynil and/or bromoxynil phenol, in orderto form a water-soluble salt thereof.
By weak acid is meant an organic or an inorganic acid with dissociation contant Ka between 10-8 and 10-3.
Sodium and potassium ions are preferred as alkali metal kations.
Suitable salts of weak acids are, for example, acetates, carbonates, hydrogencarbonates, hydrogenphosphites, di-hydrogenphosphates, hydrogenphosphates, nitrites, hydrogen-sulphites and polycarboxylates such as malonates.
Preferred alkali metal salts of weak acids are sodium-carbonate, potassiumcarbonate, sodium acetate, sodium malonate and sodium hydrogenphosphite. A very particularly preferred alkali metal salt of a weak acid is sodium carbonate.
Simple phenolic formulations can be prepared which contain sodium or potassium salts of weak acids. These active ingredients when added to the spray tank will dissolve, leaving solutions of spray liquor. The benefits of using these types of solid formulations are:
The less irritant and less moisture sensitive HBN phenols can be used in the preparation.
The formulations in their solid form are very simple in their composition and can be prepared with or without the use of 200Z4~4 wetting or dispersing aids. The formulations can contain water-soluble carriers or fillers.
Compositions according to the present invention also maycon-tain minor amounts of anionic surfactants. Suitableanionic surfactants are polymer- or copolymer-moleculescontaining hydrophilic groups which are capable of forminganions, for example, polymer- or copolymer-moleculescontaining carboxyl groups, sulfuric acid ester groups, sulphonic acid groups or phosphoric acid ester groups.Preferred polymer-molecules are polyacrylates, alkali metal salts ofdiisobutylene maleicacid copolymers, ligninsulphonates andcondensed alkyl arylsulpho-nates. A particularly preferredanionic surfactant isthe sodium salt of diisobutylene maleicacid copolymer.
Suitable groups of water-soluble carriers or fillers may be organicandinorganic salts, ureas and sugars. Preferred water-soluble carriers or fillers are ureas and inorganic salts.Particularlypreferred water soluble carriers or fillers are inorganicsalts, forexample sodium sulphate, potassium sulphate, sodium chloride, potassium chloride, sodium nitrate, potassium nitrate and calcium nitrate but in particularsodium sulphate.
The fact that the active ingredients and in many cases the formulation dissolves in the spray tank gives rise to a non sedimenting spray liquor which can be successfully sprayed over an extended period of time.
Because of the solubility of the formulations, fine grinding of active ingredients is unnecessary.
Another method of exploiting these formulations is that they can be granulated to reduce the level of dust which is generally considered as an undesirable property.
20024~4 Granulation of these formulations can be effected using techniques such as compaction, extrusion, agglomeration or spray drying. Compaction granulation involves compressing dry powder components to form solid sheets which aresub-sequently broken down into granules, using a suitable crusher. Extrusion granulation comprises pressing a paste or wetted powderofthe formulation through a screen; the material extruded isthendried and broken down to granules of a convenient size.Agglomeration granulation comprises spraying a liquid, whichis usually aqueous, into a fluidized powder. The powder agglomerates, form larger particles which are subsequentlydried.
Spray drying granulation involves preparing a solution or suspensionof the formulation, and spraying the solution or suspension down a hot column of air. The droplets arethereby dried to form spherical granules. In the case ofspray drying, reaction will occur between the HBN phenol andthe salt of the weak acid during the preparation of thesolution or slurry. Consequently, HBN salt will be formed, therefore, during this granulation technique. Salt formationmay also occur, to some extent, during extrusion oragglomeration granulation procedures, when quantities ofaqueous medium are added prior to, and during granulationrespectively. No detrimental effect is observed on thequality of theformula-tion.
Another aspect of the formulation of the present invention is the fact that the HBN components can be mixed with other soluble active ingredients such as soluble salts ofchloro-phenoxyalkanoic acids i.e. Mecoprop or sulphonylurease.g.
Triasulfuron. In the case of Triasulfuron, which is apotent herbicide, the solubility increases with increasing pH. It is insoluble at pH 2.5 but has a solubility of 1.5 g/1 at pH7. However, in view of the hydrolysis of Triasulfuron at low pH-values, pH 5-6representsanoptimum.
200Z4'74 The granules produced in these cases still have the same property of being fully dispersible and soluble once stirred into the spray liquor.
The following Examples further illustrate the present invention.
Examples l to 3: Compositions comprising ioxynil and bromoxynil in their phenol form as well as a salt of a weak acid are formulated and have the compositions as set out in Table I.
Table I
Component % w~w % w~w% w/w Ioxynil as phenol 30 30 30 Bromoxynil as phenol 30 30 30 Sodium Carbonate 15 20 to 100%
Sodium Sulphate to 100 % to 100 %
Sodium salt of maleic acid diisobutylen copolymer 0 - 2 0 - 2 0 - 2 The powdered components are homogenised and then granulated by one of the previously mentioned techniques. The result is water soluble granules that eventually dissolve in the spray liquor.
Example 4: A formulation similar to that of Examples 1 to 3, but containing Mecoprop in salt form, is made up and has the composition set out in Table II.
Table II
Component % w/w Ioxynil as phenol 5.0 Bromoxynil as phenol 5.0 Mecoprop asTriethanolamine salt 46.5 Sodium salt of maleic acid diiso-butylene copolymer 2.0 Sodium Carbonate 1.0 Sodium Sulphate to 100 %
The powdered components may be homogenised ln a suitable blender then granulated by first compacting then sieving to a desirable particle size.
Example 5: The formulation defined in Table III is made up:
Table III
Component % w/w Triasulfuron 0.25 Ioxynil as phenol 5.0 Bromoxynil as phenol 5.0 Mecoprop as magnesium salt or Triethanolamine salt 46.75 Sodium salt of maleic acid diisobutylene copolymer 1.0 Sodium Carbonate 1.0 Sodium Sulphate to 100 %
The formulation is granulated using the technique described in Example 4.
Claims (5)
1. A herbicidal composition comprising ionoxynil and/or bromoxynil in their phenolic form, together with an alkali metal salt of a weak acid.
2. A herbicidal composition according to claim 1 wherein the salt of the weak acid is present in an amount which is at least the stoichiometric amount required to react with the ioxynil and/or bromoxynil phenol to form a water-soluble salt thereof.
3. A herbicidal composition according to claim 1 or 2 wherein the alkali metal salt of the weak acid is a sodium or potassium salt of carbonic acid, a polycarboxylic acid or phosphoric acid.
4. A herbicidal composition according to claim 1 substantial-ly as described with reference to any of the Examples.
5. Spray liquor comprising a composition according to any of the preceding claims, dissolved in water.
FO 7.5/IH/sm*/cc*
FO 7.5/IH/sm*/cc*
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB888826320A GB8826320D0 (en) | 1988-11-10 | 1988-11-10 | Soluble herbicidal preparations |
| GB8826320.7 | 1988-11-10 | ||
| GB898906617A GB8906617D0 (en) | 1989-03-22 | 1989-03-22 | Soluble herbicidal preparations |
| GB8906617.9 | 1989-03-23 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2002474A1 true CA2002474A1 (en) | 1990-05-10 |
Family
ID=26294603
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002002474A Abandoned CA2002474A1 (en) | 1988-11-10 | 1989-11-08 | Solid herbicidal preparations |
Country Status (6)
| Country | Link |
|---|---|
| EP (1) | EP0368806A1 (en) |
| JP (1) | JPH02191203A (en) |
| AU (1) | AU617893B2 (en) |
| BR (1) | BR8905749A (en) |
| CA (1) | CA2002474A1 (en) |
| IL (1) | IL92189A0 (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8909380D0 (en) * | 1989-04-25 | 1989-06-14 | Marks A H & Co Ltd | Water soluble pesticide solution |
| US5280008A (en) * | 1991-08-16 | 1994-01-18 | Pbi-Gordon Corporation | Dry, water-soluble powder, substituted heterocyclic acid or substituted phenol herbicidal compositions, and method of preparing same |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE637794A (en) * | 1962-09-24 | |||
| FR2509575A1 (en) * | 1982-06-25 | 1983-01-21 | Rhone Poulenc Agrochimie | Effervescent herbicidal granules - contg. acid herbicide and alkali metal carbonate |
| FR2589325B1 (en) * | 1985-11-04 | 1988-12-09 | Produits Ind Cie Fse | DELITABLE GRANULES BASED ON SUBSTANCES WITH PHYTOPHARMACEUTICAL ACTIVITY AND THEIR PREPARATION METHOD |
-
1989
- 1989-11-02 IL IL92189A patent/IL92189A0/en unknown
- 1989-11-02 EP EP89810826A patent/EP0368806A1/en not_active Withdrawn
- 1989-11-08 CA CA002002474A patent/CA2002474A1/en not_active Abandoned
- 1989-11-09 AU AU44517/89A patent/AU617893B2/en not_active Ceased
- 1989-11-10 JP JP1293797A patent/JPH02191203A/en active Pending
- 1989-11-10 BR BR898905749A patent/BR8905749A/en not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| AU4451789A (en) | 1990-05-17 |
| IL92189A0 (en) | 1990-07-26 |
| EP0368806A1 (en) | 1990-05-16 |
| BR8905749A (en) | 1990-06-05 |
| AU617893B2 (en) | 1991-12-05 |
| JPH02191203A (en) | 1990-07-27 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued |