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
  • A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
  • A01N25/08—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing solids as carriers or diluents

Definitions

• the present invention relates to an improved agrochemical formulation. More specifically, the present invention relates to a solid controlled release agrochemical formulation.
• the agrochemical formulation is a herbicidal formulation, more preferably one which comprises a /7-hydroxyphenylpyruvate dioxygenase (HPPD) inhibitor.
• HPPD /7-hydroxyphenylpyruvate dioxygenase
• the present invention further relates to a method of controlling undesirable vegetation at a locus using said formulation.
• the protection of crops from weeds and other vegetation that inhibits crop growth is a constantly recurring problem in agriculture. To help combat this problem, researchers in the field of synthetic chemistry have produced an extensive variety of chemicals and chemical formulations effective in the control of such unwanted growth.
• Chemical herbicides of many types have been disclosed in the literature and a large number are in commercial use. Commercial herbicides and some that are still in development are described in The Pesticide Manual, 12 th edition, published in 2000 by the British Crop Protection Council.
• 'selective' herbicides which are chosen to kill the weeds while leaving the crop undamaged.
• few herbicides are fully selective, in that they will kill all the weeds and leave the crop untouched at a particular application rate.
• the use of most selective herbicides is actually a balance between applying enough herbicide to acceptably control most of the weeds and causing only minimal crop damage.
• One known selective herbicide is mesotrione, 2-(4-methylsulphonyl-2- nitrobenzoyl)cyclohexane-l ,3-dione, an HPPD inhibitor.
• Mesotrione is usually formulated for sale as a concentrated suspension of solid mesotrione in water.
• the concentrate typically contains between 100 and 500g/l of mesotrione.
• This concentrate is then diluted by the end user, shortly before application, to give a final ready-to-use composition that typically comprises between 1 and lOg/1 of mesotrione.
• solid herbicidal formulations are preferred.
• solid formulations - especially granules - can be particularly useful in respect of paddy field applications, where the end-user can apply the herbicide containing granule directly to the paddy field water, wherein the herbicide is subsequently released from the granule in order to provide the necessary weed control.
• an improved solid agrochemical formulation comprising:-
• agrochemical includes, for example, insecticides, fungicides (e.g pyroquilon), herbicides and plant growth regulators (e.g trinexapac-ethyl). It should be understood that many agrochemicals having a pKa from 2 to 7 have potential utility with regard to the controlled release formulation of the present invention.
• the agrochemical is a herbicide - more preferably one selected from the group consisting of a HPPD inhibitor, glyphosate (including salts therefore and in particular the potassium salt) and a sulphonylurea herbicide (especially bensulfuron- methyl).
• the herbicide is a HPPD inhibitor is selected from the group consisting of isoxazoles, triketones, pyrazoles, benzobicyclon and ketospiradox.
• the isoxazole is a compound of formula (IA)
• R is hydrogen or -CO 2 R ;
• R 1 is C L4 alkyl or C 3-6 cycloalkyl optionally substituted by Ci -6 alkyl;
• R 2 is independently selected from the group consisting of halogen, nitro, cyano, amino, Ci -4 alkyl, Ci -4 haloalkyl, Ci -6 alkoxy, Ci -6 alkoxy-Ci- 6 alkyl, Ci -6 alkoxy-
• Ci -4 alkyl -(CR 4 R 5 ) c S(O) b R 6 , -S(O) b R 6 , -OSO 2 R 6 and -N(R 7 )SO 2 R 6 ;
• R 3 is Ci -4 alkyl;
• R 4 and R 5 are independently hydrogen or Ci -4 alkyl
• R 6 is C M alkyl
• R 7 is hydrogen or C] -6 alkyl; a is one, two or three; b is zero, one or two; and c is one or two (where c is two, the groups (CR 4 R 5 ) may be the same or different).
• R is hydrogen;
• R 1 is cyclopropyl;
• R 2 is halogen (preferably chloro), or Ci -4 haloalkyl (preferably trifluorom ethyl); and a is two.
• Particularly preferred compounds of formula (IA) include 5-cyclopropyl-4-(2- methylsulfonyl-4-trifluoromethyl)benzoylisoxazole (isoxaflutole) and 4-(2-chloro-4- methylsulphonyl)benzoyl-5-cyclopropylisoxazole (isoxachlortole), especially isoxaflutole.
• the triketone is a 2 -benzoyl- 1 ,3-cyclohexanedione of formula (IB),
• R 8 is selected from the group consisting of halogen, nitro, Ci -4 alkyl, Ci -4 haloalkyl, Ci -6 alkoxy, Ci -6 alkoxy-Ci -6 alkyl, Ci -6 alkoxy-C 2-6 alkoxy, Ci -6 alkoxy-C 2-6 -alkoxy-Ci -6 alkyl, Ci -4 haloalkoxy and Ci -4 haloalkoxy-Ci -4 alkyl.
• R 8 is chloro or nitro.
• R 2 is preferably selected from the group consisting Of -SO 2 CH 3 , CF 3 and 2,2,2 trifluoroethoxymethyl.
• Preferred compounds of formula (IB) are 2-(2'-nitro-4'- methylsulphonylbenzoyl)-l,3-cyclohexanedione (mesotrione), 2-(2'-nitro-4'- methylsulphonyloxybenzoyl)-l,3-cyclohexanedione, 2-(2'-chloro-4'- methylsulphonylbenzoyl)-l ,3-cyclohexanedione (sulcotrione), 2-[2-chloro-4- (methylsuphonyl)-3-[2,2,2-trifluoroethoxy]methyl]benzoyl]-l,3-cyclohexanedione (tembotrione), 4,4-dimethyl-2-(4-methanesulphonyl-2-nitrobenzoyl)-l,3- cyclohexanedione, 2-(2-chloro-3-ethoxy-4- methanesulphonyl
• the triketone may also be of formula (IC)
• R 2 is preferably selected from the group consisting of -SO 2 CH 3 , CF 3 and methoxyethoxymethyl.
• the triketone of formula (IC) is 4- Hydroxy-3-[2-(2-methoxyethoxymethyl)-6-trifluoromethylpyridine-3-carbonyl]- bicyclo[3.2.1 ]oct-3-en-2-one).
• the pyrazole is a compound of formula (ID) wherein:
• R 9 and R 10 are each independently selected from the group consisting of hydrogen, halo and Ci -4 alkyl;
• R 2 is preferably selected from the group consisting of methyl, -SO 2 CH 3 and CF 3 .
• the pyrazole of formula (ID) is 5- hydroxyl- 1 ,3-dimethyl- 1 H-pyrazol-4-yl)[2-(methylsulfonyl)-4- 'i(trifluoromethyl)phenyl]methanone (pyrasulfotole).
• pyrazoles are compounds of formula (IE)
• R 11 is Ci -2 alkyl or chloro
• R 12 is hydrogen or Ci -4 alkyl
• R 13 is C 1 -4 alkyl.
• the pyrazole of compound (IE) is [3-(4,5-dihydro-3- isoxazolyl)-2-methyl-4-(methylsulfonyl)phenyl](5-hydroxy-l -methyl- lH-pyrazol-4- yl)methanone (topramesone).
• Benzobicyclon is a compound of formula (IF)
• Ketospiradox is a compound of formula (IG)
• the HPPD-inhibiting herbicide is selected from the group consisting of mesotrione, sulcotrione, tembotrione, 4- Hydroxy-3-[2-(2-methoxyethoxymethyl)-6-trifluoromethylpyridine-3-carbonyl]- bicyclo[3.2.1]oct-3-en-2-one), isoxaflutole and pyrasulfotole. Particularly preferred is wherein the HPPD-inhibiting herbicide is mesotrione.
• HPPD inhibitors also includes, for example, reference to tautomers and agriculturally acceptable salts thereof.
• agriculturally acceptable salts include alkali metal salts such as sodium or potassium, alkaline earth metal salts such as magnesium or calcium, amine salts such as a monomethyl amine, dimethylamine, tri ethyl amine, ammonium salts or dimethyl ammonium salts.
• the herbicide may also be provided as a metal chelate.
• Metal ions which may be useful in forming the metal chelate include di- and trivalent transition metal ions such as Cu 2+ , Zn 2+ , Co 2+ , Fe 2+ , Ni 2+ and Fe 3+ .
• water-soluble aluminium salts include, for example, aluminium sulphate, poly aluminium chloride, aluminium silicate, aluminium chloride, aluminium nitrate, sodium aluminate and ammonium aluminium sulphate. Aluminium sulphate and basic aluminium chloride are particularly preferred.
• silicate mineral is taken to mean a silicate-based inorganic substance having adsorptive property or capable of ion exchanging, e.g. bentonite, montmorilonite, zeolite, sepiolite, pyrophilite, kaolinite, talc and hydrotalcite. Bentonite and montmorilonite are particularly preferred.
• the weight ratio of the HPPD inhibitor: silicate mineral in the formulation of the present invention is from 1%: 5% to 1%: 95% w/w and preferably from 1%: 10% to 1%: 70% w/w - more preferably from l%:10% to 1%: 60% w/w.
• the formulation comprises from 0.1% to 10% w/w of HPPD inhibitor.
• the formulation of the present invention comprises from 1% to 20% w/w of water-soluble aluminium salt preferably from 2% to 10% w/w.
• the formulation comprises from 5% to 95% w/w of silicate mineral, preferably 10% to 70% w/w. All percentages are expressed as a proportion of the total solid formulation.
• the herbicidal formulation may further comprise or may be applied in combination with one or more additional active ingredients.
• additional active ingredients include herbicides, fungicides, insecticides and the like.
• herbicides include, but are not limited to, Bensulfuron methyl, CNP, Naproanilide, Bifenox, Pyributicarb, Bromobutide, Mefenacet, Daimuron, Imazosulfuron, Pyrazosulfuron ethyl, Simetryn, Prometryn, Dimethametryn, Chlomethoxynil, Oxadiazon, Pyrazolate, Pyrazoxyfen, Clomeprop, Benzofenap,
• insecticides include, but are not limited to Cyanophos, Fenthion, Fenitrothion, Dichlofenthion, Primiphos-methyl, Diazinon, Isoxathion, Oxydeprofos, Marathion, Phenthoate, Formothion, Thiometon, Disulfoton, Prothiophos, Sulprofos, Propenofos, Pyraclofos, Dichlorvos, Naled, Chlorfenvinphos, Propaphos, Isofenphos, Etion, Carbosulfan, Benfuracarb, Allethrin, Permethrin, Cyhalothrin, Cyfluthrin, Fenvalerate, Flucythrinate, Fluvalinate, Cycloprothrin, Silafluofen, Propargite, Halfenprox, Ethoprophos and Fosthiazate.
• fungicides include, but are not limited to, Cyprodinil, Mepanipyrim, Pyrimethanil, Metalaxyl, Mepronil, Flutolanil, Tecloftalam, Pencycuron, Diclomezine, Triflumizole, Kasugamycin, Validamycin, Probenazole, Isoprothiolane, Cyproconazole, Metconazole, Tricyclazole, Pyroquilon, Oxolinic acid, Ferimzone, Iprodione, Triforine, Picoxystrobin, Azoxystrobin, Kresoxim- methyl, Orysastrobin, Pyraclostrobin, Trifloxystrobin, Metominostrobin, Calcium polysulfide, Ediphenfos, Propiconazole, Pefurazoate, Pyrifenox, Tetreconazloe, Echlomezole, Dinocap, and Metalaxyl-M.
• the solid herbicidal formulation of the present invention may further comprise various adjuvants and carriers known to or used in the industry for facilitating dispersion.
• the choice of formulation and mode of application for any given compound may affect its activity, and selection will be made accordingly.
• the solid herbicidal formulation of this invention may be a dustable powder, a wettable powder, a granule, a water dispersible granule, a water- dispersable or water-foaming tablet, a briquette or other solid forms known in the art.
• the formulations are prepared by admixing the active ingredients with adjuvants including diluents, extenders, carriers, and conditioning agents to provide formulations in the form of finely-divided particulate solids, granules and pellets.
• adjuvants including diluents, extenders, carriers, and conditioning agents.
• Suitable agricultural adjuvants and carriers that are useful in preparing the formulations of the invention are well known to those skilled in the art.
• Suitable solid carriers include talc, titanium dioxide, pyrophyllite clay, kaolin clay, silica, attapulgite clay, kieselguhr, chalk, diatomaceous earth, lime, calcium carbonate, bentonite clay, Fuller's earth, cotton seed hulls, wheat flour, soybean flour, pumice, wood flour, walnut shell flour, lignin, and the like.
• a broad range of surface-active agents are advantageously employed in both solid and liquid formulations, especially those designed to be diluted with carrier before application.
• the surface-active agents can be anionic, cationic, nonionic or polymeric in character and can be employed as emulsifying agents, wetting agents, suspending agents, or for other purposes.
• Typical surface active agents include salts of alkyl sulfates, such as diethanolammonium lauryl sulfate; alkylarylsulfonate salts, such as calcium dodecylbenzenesulfonate; alkylphenol-alkylene oxide addition products, such as nonylphenol-C.sub.18 ethoxylate; alcohol-alkylene oxide addition products, such as tridecyl alcohol-C.sub.16 ethoxylate; soaps, such as sodium stearate; alkylnaphthalenesulfonate salts, such as sodium dibutylnaphthalenesulfonate; dialkyl esters of sulfosuccinate salts, such as sodium di(2-ethylhexyl) sulfosuccinate; sorbitol esters, such as sorbitol oleate; quaternary amines, such as lauryl trimethylammonium chloride; polyethylene glycol est
• adjuvants commonly utilized in agricultural formulations include crystallization inhibitors, viscosity modifiers, suspending agents, spray droplet modifiers, pigments, antioxidants, foaming agents, light-blocking agents, compatibilizing agents, antifoam agents, sequestering agents, neutralizing agents and buffers, corrosion inhibitors, dyes, odorants, spreading agents, penetration aids, micronutrients, emolients, lubricants, sticking agents, dispersing agents, thickening agents, freezing point depressants, antimicrobial agents, and the like.
• the formulations can also contain other compatible components, for example, other herbicides, herbicide safeners, plant growth regulants, fungicides, insecticides, and the like and can be formulated with liquid fertilizers or solid, particulate fertilizer carriers such as ammonium nitrate, urea and the like or mixed with sand, or dirt (in the case of solid - granular application).
• other compatible components for example, other herbicides, herbicide safeners, plant growth regulants, fungicides, insecticides, and the like and can be formulated with liquid fertilizers or solid, particulate fertilizer carriers such as ammonium nitrate, urea and the like or mixed with sand, or dirt (in the case of solid - granular application).
• the formulation of the present invention can be prepared in various solid forms such as granular formulation, jumbo formulation or the like. Conventional methodology, well known to the skilled person, can be used to prepare the formulation of the present invention. For example, a granular formulation may be prepared in the following manner.
• HPPD inhibitor(s), water soluble aluminium salt (s), silicate mineral(s) and other ingredients are mixed uniformly. Amounts of the ingredients to be mixed are selected such that their contents in the formulation become as those described hereinbefore. If necessary, HPPD inhibitor(s) and other agrochemical(s) are beforehand ground in order for them to be uniformly mixed with other ingredients. Then, water or another suitable solvent is added to the thus obtained uniform mixture, which is then kneaded using a kneader and subsequently subject to extrusion granulation by means of an extruder. The granules thus formed are dried and subject to particle size adjustment, whereby the formulation of the present invention is prepared.
• the formulation can be prepared by any conventional method e.g extruder granulation, compression formation, granulation by fluidized bed, pan granulation or the like.
• the present invention still further provides a method of controlling undesirable vegetation at a locus which comprises applying to the locus a controlling amount a herbicidal formulation according to the present invention.
• the method relates to selectively controlling weeds in rice, in particular weeds in transplanted and direct- seeded rice.
• the herbicidal formulation is applied directly into the paddy field water.
• solid herbicidal formulations can be applied to the locus using a variety of means - for example by hand or by machine direct.
• the method can be used to control weeds in indica-type or japonica-type rice varieties.
• the method is particularly suited to the control of undesired weeds emerging in paddy fields such as Amaranthaceae, Caryophyllaceae, Chenopodiaceae, Commelinaceae, Compositae, Convolvulaceae, Cruciferae, Cyperaceae, Equisetaceae, Euphorbiaceae, Gramineae, Labiatae, Leguminosae, Malvaceae, Oxlidaceae, Portulaacaceae, Polygonaceae, Rubiaceae, Scrophulariaceae, Solanaceae, Violaceae and Umbelliferae.
• Amaranthaceae Caryophyllaceae, Chenopodiaceae, Commelinaceae, Compositae, Convolvulaceae, Cruciferae, Cyperaceae, Equisetaceae, Euphorbiaceae, Gramineae, Labiatae, Leguminosae, Malvaceae, Oxlidaceae
• the solid herbicidal formulation of the present invention may be applied to the paddy field water either before or shortly after seeding.
• the herbicidal formulation is applied before seeding or after seeding but pre-emergence of the rice crop.
• the solid herbicidal formulation of the present invention may be applied to the paddy field water before or after transplanting of rice.
• the rate at which the HPPD inhibitor is applied will depend on a number of factors, for example the weeds to be controlled, the climatic conditions etc. In general an application rate of between 0.5g ai/ha and 500g ai/ha is appropriate, for example between 50g and 250g ai/ha. The specific rate to be applied will be readily determinable by the skilled person.
• an HPPD inhibitor are when mixed using a mixer to obtain uniform powder, to which 10 parts by weight of a ca. 30% aqueous aluminium sulfate solution (a product of Toshin Kagaku Co., Ltd.) are added, followed by mixing to obtain a uniform mixture. Then, water is added and the mixture is further subject to mixing. The amount of water added is 15% by weight based on the total weight of the mixture including the water added. The thus prepared mixture is then subject to granulation by means of a basket extruder, followed by drying and sieving, whereby a granular formulation containing mesotrione in an amount of 1 % by weight, based on the total weight of the formulation, is obtained.
• a aqueous aluminium sulfate solution a product of Toshin Kagaku Co., Ltd.
• the above prepared formulation is subject to release tests to measure the release behaviour of mesotrione.
• NK300 a product of Showa Chemical (Co., Ltd., filler)
• 25 parts by weight of Na-bentonite Kunigel V-I, a product of Kunimine Kogyo Co., Ltd., a silicate mineral
• 2 parts by weight of dextrin Dextrin ND-S, a product of Niommen Kagaku Co., Ltd., a binder material
• 3 parts by weight of an anionic surfactant SORPOL 5060, a product of Toho Chemical Co., Ltd,
• mesotrione purity ca.
• a product of Syngenta Crop Protection AG, an HPPD inhibitor are well mixed using a mixer to obtain uniform powder, to which 20 parts by weight of a ca. 30% aqueous aluminium sulphate solution (a product of Toshin Kagaku Co., Ltd,) are added, followed by mixing to obtain a uniform mixture. Then, water is added and the mixture is further subject to mixing. The amount of water added is 10% by weight based on the total weight of the mixture including the water added. The thus prepared mixture is then subject to granulation by means of a twin screw extruder, followed by drying and sieving, whereby a granular formulation containing mesotrione in an amount of 1 % by weight, based on the total weight of the formulation, is obtained.
• NK300 a product of Showa Chemical Co., Ltd., filler
• 25 parts by weight of Na-bentonite (Kunigel V-I, a product of Kunimine Kogyo Co., Ltd., a silicate mineral)
• 2 parts by weight of dextrin Dextrin ND-S, a product, of Niommen Kagaku Co., Ltd., a binder material
• 3 parts by weight of an anionic surfactant SORPOL 5060, a product of Toho Chemical Co., Ltd.
• 2 parts by weight of citric acid purity ca. 99%, a product of Merck
• mesotrione purity ca.
• a product of Syngenta Crop Protection AG, an HPPD inhibitor are well mixed using a mixer to obtain uniform powder, to which 20 parts by weight of a ca. 30% aqueous basic aluminum chloride solution (a product of Toshin Kagaku Co., Ltd.) arc added, followed by mixing to obtain a uniform mixture. Then, water is added and the mixture is further subject to mixing. The amount of water added is 15% by weight based on the total weight of the mixture including the water added.
• the thus prepared mixture is then subject to granulation by means of a pan granulator, followed by drying and sieving, whereby a granular formulation containing mesotrione in an amount of 1 % by weight, based on the total weight of the formulation, is obtained.
• the above prepared formulation is subject to release tests to measure the release behaviour of mesotrione in the same manner as in Example 1.
• the results from the release tests are as follows: Time elapsed (days) Mesotrione released (%)
• clay 65.5 parts by weight of clay (NK300, a product of Showa Chemical Co., Ltd., filler), 25 parts by weight of montmolironite (Kunipia F, a product of Kunimine Kogyo Co., Ltd., a silicate mineral, 5 parts by weight of starch (Amicol C, a product of Nippon Starch Chemical Co., Ltd., a binder material, 0.5 parts by weight of an anionic surfactant (Newkalgen EP70G, a product of Takemoto Oil & Fat Co., Ltd.) and 1.33 parts by weight of mesotrione (purity ca.
• a product of Syngenta Crop Protection AG, an HPPD inhibitor are well mixed using a mixer to obtain uniform powder, to which 10 parts by weight of a ca. 30% aqueous polyaluminum chloride solution (a product of Toshin Kagaku Co., Ltd.) are added, followed by mixing to obtain a uniform mixture. Then, water is added and the mixture is further subject to mixing. The amount of water added is 10% by weight based on the total weight of the mixture including the water added. The thus prepared mixture is then subject to granulation by means of a disc pelleter, followed by drying and sieving, whereby a granular formulation containing mesotrione in an amount of 1 % by weight, based on the total weight of the formulation, is obtained.
• clay 93.5 parts by weight of clay (NK300, a product of Showa Chemical Co., Ltd., filler), 2 parts by weight of dextrin (Dextrin ND-S, a product of Niommen Kagaku Co., Ltd., a binder material), 0.5 parts by weight of an anionic surfactant.
• Newkalgen EP70G a product of Takemoto Oil & Fat Co., Ltd,
• mesotrione purity ca. 75%, a product of Syngenta Crop Protection AG, an HPPD inhibitor
• aqueous aluminium sulfate solution (a product of Toshin Kagaku Co., Ltd.) are added, followed by mixing to obtain a uniform mixture. Then, water is added and the mixture is further subject to mixing. The amount of water added is 15% by weight based on the total weight of the mixture including the water added.
• the thus prepared mixture is then subject to granulation by means of a basket extruder, followed by drying and sieving, whereby a granular formulation containing mesotrione in an amount of 1 % by weight, based on the total weight of the formulation, is obtained.
• the above prepared formulation is subject to release tests to measure the release behaviour of mesotrione in the same manner as in Example 1.
• the results from the release tests are as follows: Time elapsed (days) Mesot ⁇ one released (%)
• clay 71.5 parts by weight of clay (NK300, a product of Show a Chemical Co., Ltd., filler), 25 parts by weight of Na-bentonite (Kunigel V-I, a product of Kunimine Kogyo Co., Ltd., a silicate mineral), 2 parts by weight of dextrin (Dextrin ND-S, a product of Niommen Kagaku Co., Ltd., a binder material), 0.5 parts by weight of an anionic surfactant (Newkalgen EP7OG, a product of Takemoto Oil & Fat Co., Ltd,) and 1.33 parts by weight of mesotrione (purity ca.
• anionic surfactant Newkalgen EP7OG, a product of Takemoto Oil & Fat Co., Ltd,
• a product of Syngenta Crop Protection AG, an HPPD inhibitor are well mixed using a mixer to obtain uniform powder, to which 10 parts by weight of water are added, followed by mixing to obtain a uniform mixture.
• the thus prepared mixture is then subject to granulation by means of a basket extruder, followed by drying and sieving, whereby a granular formulation containing mesotrione in an amount of 1 % by weight, based on the total weight of the formulation, is obtained.
• the above prepared formulation is subject to release tests to measure the release behaviour of mesotrione in the same manner as in Example 1.
• the results from the release tests are as follows:
• kaolin clay a product of Showa Chemical Co., Ltd., filler
• 25 parts by weight of Na-bentonite Kunigel V-I, a product of Kunimine Kogyo Co., Ltd., a silicate mineral
• 2 parts by weight of dextrin Dextrin ND-S, a product of Niommen Kagaku Co., Ltd., a binder material
• 3 parts by weight of an anionic surfactant SORPOL 5060, a product of Toho Chemical Co., Ltd.
• 10 parts by weight of calcium chloride 1.33 parts by weight of mesotrione (purity ca.
• a product of Syngenta Crop Protection AG, an HPPD inhibitor) and 23 parts by weight of water are well mixed using a mixer to obtain a uniform mixture.
• the thus prepared mixture is then subject to granulation by means of a basket extruder, followed by drying and sieving, whereby a granular formulation containing mesotrione in an amount of 1% by weight, based on the total weight of the formulation, is obtained.
• the above prepared formulation is subject to release tests to measure the release behaviour of mesotrione in the same manner as in Example 1.
• the results from the release tests are as follows:

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