NL1036979C2 - Water dispersible granule. - Google Patents
Water dispersible granule. Download PDFInfo
- Publication number
- NL1036979C2 NL1036979C2 NL1036979A NL1036979A NL1036979C2 NL 1036979 C2 NL1036979 C2 NL 1036979C2 NL 1036979 A NL1036979 A NL 1036979A NL 1036979 A NL1036979 A NL 1036979A NL 1036979 C2 NL1036979 C2 NL 1036979C2
- Authority
- NL
- Netherlands
- Prior art keywords
- water
- weight
- parts
- dispersible granule
- present
- Prior art date
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- 239000004562 water dispersible granule Substances 0.000 title claims description 111
- 238000005469 granulation Methods 0.000 claims description 90
- 230000003179 granulation Effects 0.000 claims description 90
- 238000005507 spraying Methods 0.000 claims description 78
- PGOOBECODWQEAB-UHFFFAOYSA-N (E)-clothianidin Chemical compound [O-][N+](=O)\N=C(/NC)NCC1=CN=C(Cl)S1 PGOOBECODWQEAB-UHFFFAOYSA-N 0.000 claims description 75
- 239000005888 Clothianidin Substances 0.000 claims description 75
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 70
- 239000007787 solid Substances 0.000 claims description 64
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 63
- 239000000126 substance Substances 0.000 claims description 44
- 239000000725 suspension Substances 0.000 claims description 38
- 238000000034 method Methods 0.000 claims description 36
- 239000004375 Dextrin Substances 0.000 claims description 35
- 229920001353 Dextrin Polymers 0.000 claims description 35
- 235000019425 dextrin Nutrition 0.000 claims description 35
- 239000013543 active substance Substances 0.000 claims description 33
- 239000004615 ingredient Substances 0.000 claims description 31
- 239000004202 carbamide Substances 0.000 claims description 30
- 150000001875 compounds Chemical class 0.000 claims description 19
- 239000004094 surface-active agent Substances 0.000 claims description 17
- 239000007864 aqueous solution Substances 0.000 claims description 15
- 230000000749 insecticidal effect Effects 0.000 claims description 15
- 239000007900 aqueous suspension Substances 0.000 claims description 13
- 239000000843 powder Substances 0.000 claims description 12
- 150000003839 salts Chemical class 0.000 claims description 9
- 230000001270 agonistic effect Effects 0.000 claims description 5
- NVVZQXQBYZPMLJ-UHFFFAOYSA-N formaldehyde;naphthalene-1-sulfonic acid Chemical compound O=C.C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 NVVZQXQBYZPMLJ-UHFFFAOYSA-N 0.000 claims description 5
- 239000011324 bead Substances 0.000 claims description 4
- 229920001732 Lignosulfonate Polymers 0.000 claims description 3
- 238000005192 partition Methods 0.000 claims description 3
- 229920005646 polycarboxylate Polymers 0.000 claims description 3
- HGASFNYMVGEKTF-UHFFFAOYSA-N octan-1-ol;hydrate Chemical compound O.CCCCCCCCO HGASFNYMVGEKTF-UHFFFAOYSA-N 0.000 claims description 2
- 239000008188 pellet Substances 0.000 claims 3
- 239000007921 spray Substances 0.000 description 69
- 239000002002 slurry Substances 0.000 description 68
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 54
- 238000007873 sieving Methods 0.000 description 51
- 239000002518 antifoaming agent Substances 0.000 description 43
- ANRHNWWPFJCPAZ-UHFFFAOYSA-M thionine Chemical compound [Cl-].C1=CC(N)=CC2=[S+]C3=CC(N)=CC=C3N=C21 ANRHNWWPFJCPAZ-UHFFFAOYSA-M 0.000 description 43
- 239000008187 granular material Substances 0.000 description 42
- 238000002156 mixing Methods 0.000 description 36
- 239000011268 mixed slurry Substances 0.000 description 34
- 238000003756 stirring Methods 0.000 description 34
- 239000003905 agrochemical Substances 0.000 description 30
- -1 polyoxyethylene Polymers 0.000 description 30
- 235000017557 sodium bicarbonate Nutrition 0.000 description 27
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 27
- 238000001035 drying Methods 0.000 description 26
- 239000007788 liquid Substances 0.000 description 26
- 239000012530 fluid Substances 0.000 description 25
- 230000000052 comparative effect Effects 0.000 description 19
- XONPDZSGENTBNJ-UHFFFAOYSA-N molecular hydrogen;sodium Chemical compound [Na].[H][H] XONPDZSGENTBNJ-UHFFFAOYSA-N 0.000 description 15
- 239000007789 gas Substances 0.000 description 14
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 12
- 235000014113 dietary fatty acids Nutrition 0.000 description 11
- 239000000194 fatty acid Substances 0.000 description 11
- 229930195729 fatty acid Natural products 0.000 description 11
- 235000002639 sodium chloride Nutrition 0.000 description 10
- 239000011812 mixed powder Substances 0.000 description 9
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- 238000002360 preparation method Methods 0.000 description 8
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 7
- HOJIKECRURMVNY-UHFFFAOYSA-N carbonic acid;urea Chemical compound NC(N)=O.OC(O)=O HOJIKECRURMVNY-UHFFFAOYSA-N 0.000 description 6
- 239000000796 flavoring agent Substances 0.000 description 6
- 235000019634 flavors Nutrition 0.000 description 6
- 244000215068 Acacia senegal Species 0.000 description 5
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- 229920002472 Starch Polymers 0.000 description 5
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- 239000000205 acacia gum Substances 0.000 description 5
- 238000010790 dilution Methods 0.000 description 5
- 239000012895 dilution Substances 0.000 description 5
- 235000013399 edible fruits Nutrition 0.000 description 5
- 239000008107 starch Substances 0.000 description 5
- 235000019698 starch Nutrition 0.000 description 5
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 5
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 4
- 102000019315 Nicotinic acetylcholine receptors Human genes 0.000 description 4
- 108050006807 Nicotinic acetylcholine receptors Proteins 0.000 description 4
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 4
- 239000011230 binding agent Substances 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 239000011591 potassium Substances 0.000 description 4
- 229910052700 potassium Inorganic materials 0.000 description 4
- 235000013311 vegetables Nutrition 0.000 description 4
- 229910019142 PO4 Inorganic materials 0.000 description 3
- 229920003081 Povidone K 30 Polymers 0.000 description 3
- 229930006000 Sucrose Natural products 0.000 description 3
- 241000607479 Yersinia pestis Species 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 150000008055 alkyl aryl sulfonates Chemical class 0.000 description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- 150000001720 carbohydrates Chemical class 0.000 description 3
- 238000011437 continuous method Methods 0.000 description 3
- 150000004665 fatty acids Chemical class 0.000 description 3
- 238000000227 grinding Methods 0.000 description 3
- 239000010452 phosphate Substances 0.000 description 3
- 230000000704 physical effect Effects 0.000 description 3
- 239000005720 sucrose Substances 0.000 description 3
- WCXDHFDTOYPNIE-RIYZIHGNSA-N (E)-acetamiprid Chemical compound N#C/N=C(\C)N(C)CC1=CC=C(Cl)N=C1 WCXDHFDTOYPNIE-RIYZIHGNSA-N 0.000 description 2
- CFRPSFYHXJZSBI-DHZHZOJOSA-N (E)-nitenpyram Chemical compound [O-][N+](=O)/C=C(\NC)N(CC)CC1=CC=C(Cl)N=C1 CFRPSFYHXJZSBI-DHZHZOJOSA-N 0.000 description 2
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- XPCTZQVDEJYUGT-UHFFFAOYSA-N 3-hydroxy-2-methyl-4-pyrone Chemical compound CC=1OC=CC(=O)C=1O XPCTZQVDEJYUGT-UHFFFAOYSA-N 0.000 description 2
- 239000005875 Acetamiprid Substances 0.000 description 2
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 2
- QFOHBWFCKVYLES-UHFFFAOYSA-N Butylparaben Chemical compound CCCCOC(=O)C1=CC=C(O)C=C1 QFOHBWFCKVYLES-UHFFFAOYSA-N 0.000 description 2
- JFLRKDZMHNBDQS-UCQUSYKYSA-N CC[C@H]1CCC[C@@H]([C@H](C(=O)C2=C[C@H]3[C@@H]4C[C@@H](C[C@H]4C(=C[C@H]3[C@@H]2CC(=O)O1)C)O[C@H]5[C@@H]([C@@H]([C@H]([C@@H](O5)C)OC)OC)OC)C)O[C@H]6CC[C@@H]([C@H](O6)C)N(C)C.CC[C@H]1CCC[C@@H]([C@H](C(=O)C2=C[C@H]3[C@@H]4C[C@@H](C[C@H]4C=C[C@H]3C2CC(=O)O1)O[C@H]5[C@@H]([C@@H]([C@H]([C@@H](O5)C)OC)OC)OC)C)O[C@H]6CC[C@@H]([C@H](O6)C)N(C)C Chemical compound CC[C@H]1CCC[C@@H]([C@H](C(=O)C2=C[C@H]3[C@@H]4C[C@@H](C[C@H]4C(=C[C@H]3[C@@H]2CC(=O)O1)C)O[C@H]5[C@@H]([C@@H]([C@H]([C@@H](O5)C)OC)OC)OC)C)O[C@H]6CC[C@@H]([C@H](O6)C)N(C)C.CC[C@H]1CCC[C@@H]([C@H](C(=O)C2=C[C@H]3[C@@H]4C[C@@H](C[C@H]4C=C[C@H]3C2CC(=O)O1)O[C@H]5[C@@H]([C@@H]([C@H]([C@@H](O5)C)OC)OC)OC)C)O[C@H]6CC[C@@H]([C@H](O6)C)N(C)C JFLRKDZMHNBDQS-UCQUSYKYSA-N 0.000 description 2
- 244000024675 Eruca sativa Species 0.000 description 2
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- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- GLZPCOQZEFWAFX-UHFFFAOYSA-N Geraniol Chemical compound CC(C)=CCCC(C)=CCO GLZPCOQZEFWAFX-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 239000005906 Imidacloprid Substances 0.000 description 2
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- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 239000005930 Spinosad Substances 0.000 description 2
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 2
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- 238000010521 absorption reaction Methods 0.000 description 2
- 150000001413 amino acids Chemical class 0.000 description 2
- 239000003945 anionic surfactant Substances 0.000 description 2
- 230000002421 anti-septic effect Effects 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000003093 cationic surfactant Substances 0.000 description 2
- 239000003086 colorant Substances 0.000 description 2
- MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 description 2
- 239000013530 defoamer Substances 0.000 description 2
- YKBZOVFACRVRJN-UHFFFAOYSA-N dinotefuran Chemical compound [O-][N+](=O)\N=C(/NC)NCC1CCOC1 YKBZOVFACRVRJN-UHFFFAOYSA-N 0.000 description 2
- YDEXUEFDPVHGHE-GGMCWBHBSA-L disodium;(2r)-3-(2-hydroxy-3-methoxyphenyl)-2-[2-methoxy-4-(3-sulfonatopropyl)phenoxy]propane-1-sulfonate Chemical compound [Na+].[Na+].COC1=CC=CC(C[C@H](CS([O-])(=O)=O)OC=2C(=CC(CCCS([O-])(=O)=O)=CC=2)OC)=C1O YDEXUEFDPVHGHE-GGMCWBHBSA-L 0.000 description 2
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- QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical compound CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 description 1
- XRJLAOUDSILTFT-UHFFFAOYSA-N pyroquilon Chemical compound O=C1CCC2=CC=CC3=C2N1CC3 XRJLAOUDSILTFT-UHFFFAOYSA-N 0.000 description 1
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- 239000011780 sodium chloride Substances 0.000 description 1
- APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical compound [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 description 1
- 229940080264 sodium dodecylbenzenesulfonate Drugs 0.000 description 1
- 229940045870 sodium palmitate Drugs 0.000 description 1
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
- 235000019345 sodium thiosulphate Nutrition 0.000 description 1
- IWIUXJGIDSGWDN-UQKRIMTDSA-M sodium;(2s)-2-(dodecanoylamino)pentanedioate;hydron Chemical compound [Na+].CCCCCCCCCCCC(=O)N[C@H](C([O-])=O)CCC(O)=O IWIUXJGIDSGWDN-UQKRIMTDSA-M 0.000 description 1
- GGXKEBACDBNFAF-UHFFFAOYSA-M sodium;hexadecanoate Chemical compound [Na+].CCCCCCCCCCCCCCCC([O-])=O GGXKEBACDBNFAF-UHFFFAOYSA-M 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 238000001694 spray drying Methods 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- CVXPMURZGJUXAJ-UHFFFAOYSA-N tetraazanium carbonate sulfate Chemical compound [NH4+].[NH4+].[NH4+].[NH4+].[O-]C([O-])=O.[O-]S([O-])(=O)=O CVXPMURZGJUXAJ-UHFFFAOYSA-N 0.000 description 1
- UEUXEKPTXMALOB-UHFFFAOYSA-J tetrasodium;2-[2-[bis(carboxylatomethyl)amino]ethyl-(carboxylatomethyl)amino]acetate Chemical compound [Na+].[Na+].[Na+].[Na+].[O-]C(=O)CN(CC([O-])=O)CCN(CC([O-])=O)CC([O-])=O UEUXEKPTXMALOB-UHFFFAOYSA-J 0.000 description 1
- PYNKFIVDSJSNGL-UHFFFAOYSA-N thiosultap Chemical compound OS(=O)(=O)SCC(N(C)C)CSS(O)(=O)=O PYNKFIVDSJSNGL-UHFFFAOYSA-N 0.000 description 1
- QSOHVSNIQHGFJU-UHFFFAOYSA-L thiosultap disodium Chemical compound [Na+].[Na+].[O-]S(=O)(=O)SCC(N(C)C)CSS([O-])(=O)=O QSOHVSNIQHGFJU-UHFFFAOYSA-L 0.000 description 1
- DQJCHOQLCLEDLL-UHFFFAOYSA-N tricyclazole Chemical compound CC1=CC=CC2=C1N1C=NN=C1S2 DQJCHOQLCLEDLL-UHFFFAOYSA-N 0.000 description 1
- JARYYMUOCXVXNK-IMTORBKUSA-N validamycin Chemical compound N([C@H]1C[C@@H]([C@H]([C@H](O)[C@H]1O)O[C@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O)CO)[C@H]1C=C(CO)[C@H](O)[C@H](O)[C@H]1O JARYYMUOCXVXNK-IMTORBKUSA-N 0.000 description 1
- MWOOGOJBHIARFG-UHFFFAOYSA-N vanillin Chemical compound COC1=CC(C=O)=CC=C1O MWOOGOJBHIARFG-UHFFFAOYSA-N 0.000 description 1
- FGQOOHJZONJGDT-UHFFFAOYSA-N vanillin Natural products COC1=CC(O)=CC(C=O)=C1 FGQOOHJZONJGDT-UHFFFAOYSA-N 0.000 description 1
- 235000012141 vanillin Nutrition 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
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
- A01N25/12—Powders or granules
Landscapes
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Health & Medical Sciences (AREA)
- Toxicology (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Agronomy & Crop Science (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Description
DESCRIPTION
WATER DISPERSIBLE GRANULE 5 Technical Field
The present invention relates to a water dispersible granule.
Background Art 10 A water dispersible granule is known as an agrochemical preparation.
Disclosure of Invention
An object of the present invention is to provide a water 15 dispersible granule obtained by a certain fluidized bed granulation method.
Specifically, the present invention provides: [1] A water dispersible granule comprising at least one water-soluble agrochemical active substance which has a water 20 solubility of 100 ppm or more at 20°C and is solid at 20°C, at least one surfactant, and at least one water-soluble solid carrier which is solid at 20°C, which is obtainable by a fluidized bed granulation method comprising steps of: (A) charging a powdery substance containing at least one of the 25 water-soluble agrochemical active substance or at least one of the water-soluble solid carrier into a fluidized bed under dry airflow and allowing the powdery substance to flow, and (B) spraying an aqueous suspension of ingredients of the water dispersible granule which are not contained in the powdery 30 substance, or an aqueous solution of ingredients of the water dispersible granule which are not contained in the powdery substance, into the fluidized bed under dry airflow; [2] The water dispersible granule according to [1], wherein the proportion of the water-soluble agrochemical active substance in 35 the water dispersible granule is 10 to 80% by weight, the proportion of the surfactant in the water dispersible granule is 1036979 2 3 to 20% by weight, and the proportion of the water-soluble solid carrier in the water dispersible granule is 10 to 80% by weight; [3] The water dispersible granule according to [1] or [2], 5 wherein the powdery substance consists of at least one of the water-soluble solid carrier, and the aqueous suspension or the aqueous solution contains the water-soluble solid carrier which is different from that of the powdery substance; [4] The water dispersible granule according to any one of [1] 10 to [3], wherein the powdery substance consists of dextrin powders, and the aqueous suspension or the aqueous solution contains urea; [5] The water dispersible granule according to any one of [1] to [4], wherein the water-soluble agrochemical active substance 15 has an octanol-water partition coefficient (Log Pow) of -5 to 3; [6] The water dispersible granule according to any one of [1] to [4], wherein the water-soluble agrochemical active substance is a nicotinic acetylcholine receptor agonistic insecticidal compound; 20 [7] The water dispersible granule according to any one of [1] to [4], wherein the water-soluble agrochemical active substance is a neonicotinoide insecticidal compound; [8] The water dispersible granule according to any one of [1] to [4], wherein the water-soluble agrochemical active substance 25 is clothianidin; and [9] The water dispersible granule according to any one of [1] to [8], wherein the surfactant is lignin sulfonate, a salt of naphthalenesulfonic acid formalin condensate, or polycarboxylate.
30
Mode for Carrying Out the Invention
Specific examples of the present invention include: (1) A water dispersible granule comprising at least one water-soluble agrochemical active substance which has a water 35 solubility of 100 ppm or more at 20°C and is solid at 20°C, at least one surfactant, and at least one water-soluble solid 3 carrier which is solid at 20°C, which is obtainable by a fluidized bed granulation method comprising steps of: (A) charging a powdery substance consisting of at least one of the water-soluble solid carrier into a fluidized bed under 5 dry airflow and allowing the powdery substance to flow, and (B) spraying an aqueous suspension of ingredients of the water dispersible granule which are not contained in the powdery substance (wherein the ingredients include the water-soluble solid carrier which is different from the water-soluble solid 10 carrier used in the step (A)), or an aqueous solution of ingredients of the water dispersible granule which are not contained in the powdery substance (wherein the ingredients include the water-soluble solid carrier which is different from the water-soluble solid carrier used in the step (A) ) , into the 15 fluidized bed under dry airflow; and (2) A water dispersible granule comprising at least one water-soluble agrochemical active substance which has a water solubility of 100 ppm or more at 20°C and is solid at 20°C, at least one surfactant, and at least one water-soluble solid 20 carrier which is solid at 20°C, which is obtainable by a fluidized bed granulation method comprising steps of: (A) charging a dextrin powder into a fluidized bed under dry airflow and allowing the dextrin powder to flow, and (B) spraying an aqueous solution of urea and ingredients 25 other than dextrin of the water dispersible granule, or an aqueous suspension of urea and ingredients other than dextrin of the water dispersible granule, into the fluidized bed under dry airflow.
30 The water dispersible granule of the present invention is a water dispersible granule containing at least one water-soluble agrochemical active substance which has a water solubility of 100 ppm or more at 20°C and is solid at 20°C, at least one surfactant, and at least one water-soluble solid carrier which 4 is solid at 20°C, which is obtainable by a fluidized bed granulation method comprising steps of: (A) charging a powdery substance containing at least one of the water-soluble agrochemical active substance or at least one 5 of the water-soluble solid carrier into a fluidized bed under dry airflow and allowing the powdery substance to flow (hereinafter referred to as "step (A)"), and (B) spraying an aqueous suspension of ingredients of the water dispersible granule which are not contained in the powdery 10 substance, or an aqueous solution of ingredients of the water dispersible granule which are not contained in the powdery substance, into the fluidized bed under dry airflow (hereinafter referred to as "step (B)").
The water-soluble agrochemical active substance used in the 15 present invention has a water solubility of 100 ppm or more at 20°C and is solid at 20°C. Preferably, the water-soluble agrochemical active substance used in the present invention is solid even at 50°C. Preferably, the water-soluble agrochemical active substance used in the present invention has an octanol- 20 water partition coefficient (LogPow) of -5 to 3.
Examples of the water-soluble agrochemical active substance used in the present invention include water-soluble insecticidal compounds, water-soluble fungicidal compounds, and water-soluble herbicidal compounds.
25 Examples of the water-soluble insecticidal compound include nicotinic acetylcholine receptor agonistic insecticidal compounds. Examples of the nicotinic acetylcholine receptor agonistic insecticidal compound include neonicotinoide insecticidal compounds.
30 Specific examples of the insecticidal compound used in the present invention include: DMTP: water solubility 200 mg/1 (25°C) , LogPow 2.2;
Acephate: water solubility 790 g/1 (20°C) , LogPow -0.89; MIPC: water solubility 270 mg/1 (20°C), LogPow 2.32; 35 Methomyl: water solubility 57.9 g/1 (25°C) , LogPow 0.093; 5
Cartap hydrochloride: water solubility 200 g/1 (25°C) ;
Nitenpyram: water solubility >590 g/1 (pH 7, 20°C) , LogPow -0.66 (25°C, unstated pH);
Acetamiprid: water solubility 4,250 mg/1 (25°C), LogPow 0.8; 5 Imidacloprid: water solubility 0.61 g/1 (20°C), LogPow 0.57; Thiamethoxam: water solubility 4.1 g/1 (25°C) , LogPow -0.13;
Clothianidin: water solubility 0.304 g/1 (pH 4, 20°C) , LogPow 0.7; 10 Dinotefuran: water solubility 39.8 g/1 (20°C) , LogPow -0.549;
Thiocyclam: water solubility 16.3 g/1 (pH 6.8, 20°C), LogPow -0.07 (unstated pH);
Thiosultap-sodium: water solubility 1,335 mg/1 (20°C); 15 Thiacloprid: water solubility 185 mg/1 (20°C) , LogPow 1.26; and Spinosad: water solubility 235 ppm (spinosyn A, pH 7, 20°C),
LogPow 4.0 (spinosyn A).
Among the insecticidal compounds used in the present invention, examples of the nicotinic acetylcholine receptor 20 agonistic insecticidal compound include neonicotinoide insecticidal compounds such as imidacloprid, thiacloprid, clothianidin, thiamethoxam, nitenpyram, dinotefuran and acetamiprid; cartap hydrochloride, thiocyclam, thiosultap, and spinosad.
25 Examples of the fungicidal compound used in the present invention include:
Ferimzone: water solubility 208 mg/1 (20°C), LogPow 2.89; Furametpyr: water solubility 200 mg/1 (20°C), LogPow 2.36; Metominostrobin: water solubility 0.128 g/1 (20°C) , LogPow 2.32; 30 Myclobutanil: water solubility 132 mg/1 (20°C), LogPow 2.94; Pyroquilon: water solubility 4 g/1 (20°C), LogPow 1.6; Tricyclazole: water solubility 0.596 g/1 (20°C), LogPow 1.42; Probenazole: water solubility 150 mg/1; and 6
Validamycin: water solubility 610 * 103 mg/1 (20°C), LogPow -4.21.
Examples of the herbicidal compound used in the present invention include: 5 Fluometuron: water solubility 110 mg/1 (20°C), LogPow 2.38; Metribuzin: water solubility 1.05 g/1 (20°C), LogPow 1.6; Propanil: water solubility 130 mg/1 (20°C), LogPow 3.3; Imazosulfuron: water solubility 155.6 mg/1 (20°C), LogPow 0.05; Bentazone: water solubility 570 mg/1 (20°C), LogPow 0.77; and 10 Tebuthiuron: water solubility 2.5 g/1 (20°C), LogPow 1.82.
The water dispersible granule of the present invention can contain one or more water-soluble agrochemical active substances. The proportion of the water-soluble agrochemical active substance in the water dispersible granule of the present 15 invention is usually from 10 to 80% by weight.
The surfactant used in the present invention includes a nonionic surfactant, an anionic surfactant, a cationic surfactant and an ampholytic surfactant. Examples of the 20 surfactant used in the present invention include nonionic surfactants such as polyoxyethylene alkyl ether, polyoxyethylene alkylaryl ether, polyoxyethylene lanolin alcohol, polyoxyethylene alkylphenol formalin condensate, polyoxyethylene sorbitan fatty acid ester, polyoxyethylene glyceryl momofatty 25 acid ester, polyoxypropylene glycol monofatty acid ester, polyoxyethylene sorbitol fatty acid ester, polyoxyethylene castor oil derivative, polyoxyethylene fatty acid ester, higher fatty acid glycerin ester, sorbitan fatty acid ester, sucrose fatty acid ester, polyoxyethylene-polyoxypropylene block 30 polymer, polyoxyethylene fatty acid amide, alkylolamide, and polyoxyethylene alkylamine; cationic surfactants, for example, alkylamine hydrochloride such as dodecylamine hydrochloride; quaternary alkylammonium salt such as dodecyltrimethylammonium salt, 35 alkyldimethylbenzylammonium salt, alkylpyridinium salt, 7 alkylisoquinolinium salt and dialkylmorpholinium salt; benzetonium chloride; and polyalkylvinylpyridinium salt; anionic surfactants, for example, fatty acid sodium salt such as sodium palmitate; ether sodium carboxylate such as polyoxyethylene 5 lauryl ether sodium carboxylate; amino acid condensate of higher fatty acid such as lauroyl sarcosin sodium and sodium N-lauroyl glutamate; higher fatty acid ester sulfonate such as higher alkyl sulfonate and lauric acid ester sulfonate; dialkyl sulfosuccinate such as dioctyl sulfosuccinate; higher fatty acid 10 amide sulfonate such as oleamide sulfonate; alkyl aryl sulfonate such as sodium dodecylbenzene sulfonate and diisopropyl naphthalene sulfonate; formalin condensate of alkyl aryl sulfonate; higher alcohol sulfate such as pentadecane-2-sulfate; polyoxyethylene alkyl phosphate such as dipolyoxyethylene 15 dodecyl ether phosphate; and styrene-maleate copolymer; and ampholytic surfactants such as N-laurylalanine, N,N,N- trimethylaminopropionic acid, N,N,N- trihydroxyethylaminopropionic acid, N-hexyl-N,N- dimethylaminoacetic acid, 1-(2-carboxyethyl)pyrimidiniumbetaine, 20 and lecithin.
For suppressing the foam formation when the water dispersible granule of the present invention is diluted, the surfactant used in the present invention is preferably a sulfonate. Specific examples of the sulfonate include lignin 25 sulfonate, alkylnaphthalene sulfonate, a salt of naphthalenesulfonic acid formalin condensate, and alkyl aryl sulfonate. In view of suppression of the foam formation when the water dispersible granule of the present invention is diluted, a sodium salt of naphthalenesulfonic acid formalin 30 condensate, and lignin sulfonate are particularly preferred.
The water dispersible granule of the present invention can contain one or more surfactants. The proportion of the surfactant in the water dispersible granule of the present invention is usually from 3 to 20% by weight.
35 8
The water-soluble solid carrier used in the present invention is preferably a water-soluble solid carrier which can provide a clear dilution when the water dispersible granule of the present invention is diluted with water. As used herein, 5 the term "water-soluble solid carrier" means a solid carrier having a water solubility of 1 g/L or more at 20°C. The water-soluble solid carrier used in the present invention has preferably a water solubility of 10 g/L or more at 20°C, more preferably a water solubility of 50 g/L or more at 20°C.
10 The water-soluble solid carrier used in the present invention has preferably pH 4 to 9 at a concentration of 1% (w/w) at 20°C, more preferably pH 5 to 9 at a concentration of 1% (w/w) at 20°C. Examples of the water-soluble solid carrier used in the present invention include inorganic salts such as 15 ammonium sulfate, sodium chloride, potassium chloride, potassium dihydrogen phosphate, sodium hydrogen carbonate, sodium thiosulfate, disodium hydrogen phosphate, and sodium acetate; saccharides such as glucose, sucrose, fructose, and lactose; urea; organic acid salts; and water-soluble amino acids, and 20 preferred are saccharides. Examples of saccharides include sucrose, lactose, mannitol and dextrin, and preferred is dextrin. In the present invention, commercially available dextrin can be used. Examples of the commercially available dextrin include Dextrin ND-S (trade name; NIPPON STARCH CHEMICAL 25 CO., LTD.), Dextrin MF30 (trade name; NIPPON STARCH CHEMICAL CO., LTD.), Dextrin 4C (trade name; NIPPON STARCH CHEMICAL CO., LTD.), Tackidex B167 (trade name; ROQUETTE), and Glucidex 1 (trade name; ROQUETTE).
The water dispersible granule of the present invention can 30 contain one or more water-soluble solid carriers. The proportion of the water-soluble solid carrier in the water dispersible granule of the present invention is usually from 10 to 80% by weight.
9
The total content of the water-soluble agrochemical active substance which has a water solubility of 100 ppm or more at 20°C and is solid 20°C, the surfactant, and the water-soluble solid carrier which is solid at 20°C in the water dispersible 5 granule of the present invention is usually about 40 to 100% by weight.
The water dispersible granule of the present invention may contain an antiseptic, a colorant, a defoamer, a binder, a flavor, a sequestering agent and the like.
10 Examples of the antiseptic include methyl p- hydroxybenzoate, butyl p-hydroxybenzoate, and propyl p-hydroxybenzoate.
Examples of the colorant include rhodamines such as Rhodamine B and Solar Rhodamine; and pigments such as Sunset 15 Yellow FCF, Brilliant Blue FCF, Amaranth and Cyanine Green.
Examples of the defoamer include a silicone emulsion.
Examples of the binder include celluloses such as methyl cellulose and sodium carboxymethyl cellulose, sodium alginate; polyvinyl alcohol; polyvinyl pyrrolidone; and gum arabic. When 20 a binder is used in the present invention, the content of the binder is usually 0.5 to 10% by weight of the water dispersible granule of the present invention.
Examples of the flavor include ester-type flavors such as ethyl acetoacetate, ethyl enanthate, ethyl cinnamate and isoamyl 25 acetate; organic acid-type flavors such as caproic acid and cinnamic acid; alcohol-type flavors such as cinnamic alcohol, geraniol, citral and decyl alcohol; aldehydes such as vanillin, piperonal and perill aldehyde; ketone-type flavors such as maltol and methyl (3-naphthyl ketone; and menthol.
30 Examples of the sequestering agent include an ethylenediaminetetraacetic acid disodium salt and an ethylenediaminetetraacetic acid tetrasodium salt.
The powdery substance (hereinafter, sometimes, referred to 35 as the present powdery substance) used in the step (A) contains at least one water-soluble agrochemical active substance which 10 has a water solubility of 100 ppm or more at 20°C and is solid at 20°C, or at least one water-soluble solid carrier which is solid at 20°C, of ingredients of the water dispersible granule of the present invention. The average particle diameter of the 5 present powdery substance is usually 0.1 to 100 pm, preferably 0.1 to 50 pm.
The aqueous suspension or the aqueous solution used in step (B) (hereinafter, sometimes, referred to as the present aqueous liquid) is an aqueous suspension of ingredients of the water 10 dispersible granule which are not contained in the present powdery substance, or an aqueous solution of ingredients of the water dispersible granule which are not contained in the present powdery substance. An example of a fluidized bed granulation method for producing the water dispersible granule of the 15 present invention includes a fluidized bed granulation method which comprises using, as the present powdery substance, a powdery substance containing a water-soluble solid carrier which is solid at 20°C (for example, dextrin), and using, as the present aqueous liquid, an aqueous suspension containing a 20 water-soluble solid carrier which is solid at 20°C (for example, urea) and is different from the water-soluble solid carrier contained in the present powdery substance, or an aqueous solution containing a water-soluble solid carrier which is solid at 20°C (for example, urea) and is different from the water-25 soluble solid carrier contained in the present powdery substance.
When the present aqueous liquid is an aqueous solution, the present aqueous liquid can be prepared by dissolving ingredients of the water dispersible granule which are not contained in the 30 present powdery substance, in water.
When the present aqueous liquid is an aqueous suspension, the present aqueous liquid can be prepared, for example, by the following methods.
(1) A preparation method which comprises finely grinding 35 ingredients that should suspended into water by a wet grinding 11 method such as a bead mill, and then mixing a suspension of the water suspended ingredients with other ingredients of the present aqueous liquid.
(2) A preparation method which comprises finely grinding all 5 ingredients of the present aqueous liquid into water by wet grinding method.
(3) A preparation method which comprises finely grinding ingredients that should be suspended by a dry grinding method, and mixing the finely ground ingredients with an aqueous liquid 10 containing other ingredients of the present aqueous liquid.
The concentration of the present aqueous liquid (obtained by subtracting the weight of ingredients such as water to be removed as a result of spraying and drying from the total weight of the present aqueous liquid to calculate the weight of the 15 remaining ingredients, and then calculating the proportion of the weight of the remaining ingredients to the total weight of the present aqueous liquid) is not particularly limited and may be adjusted appropriately. The concentration of the present aqueous liquid is preferably about 10 to 70% by weight.
20 The viscosity of the present aqueous liquid is not particularly limited and may be adjusted appropriately. The viscosity of the present aqueous liquid is usually about 50 to 20,000 mPa-s (20°C, B-type viscometer, rotor No. 2, rotating speed: 6 rpm), preferably about 300 to 5,000 mPa*s.
25 The water dispersible granule of the present invention consists of a component derived from the present powdery substance and a component derived from the present aqueous liquid. A content ratio of the component derived from the present powdery substance to the component derived from the 30 present aqueous liquid in the water dispersible granule of the present invention is usually 10:90 to 90:10 (component derived from the present powdery substance: component derived from the present aqueous liquid) by weight, preferably 25:75 to 75:25 by weight.
35 A fluidized bed granulation method can be carried out using a commercially available granulator. Examples of a commercially 12 available granulator include STREA-1 (Powrex Corporation), LAB-01 (Powrex Corporation), MP-01 (Powrex Corporation), GPCG-1 (Powrex Corporation), GX-20 (Freund Corporation), FLO-5 (Freund Corporation), GPCG-2 (Glatt), GPCG-3 (Glatt), Procell 5 (Glatt), 5 MP-200 (Powrex Corporation), FLO-120 (Freund Corporation), GX- 125 (Freund Corporation), GF20 (Glatt), and GFG 500 (Glatt).
Examples of a commercially available granulator used for fluidized bed granulation by a fluidized bed spray dry method include FGA-8 (OHKAWARA KAKOHKI CO., LTD.), FSD-4 (NIRO), and 10 FGA-20 (OHKAWARA KAKOHKI CO., LTD.).
The water dispersible granule of the present invention can be obtained by a fluidized bed granulation method comprising the following two steps (A) and (B) (hereinafter, sometimes, referred to as the present fluidized bed granulation method).
15 Step (A) of: charging a powdery substance containing at least one selected from the group consisting of the water-soluble agrochemical active substance (s) and the water-soluble solid carrier(s) into a fluidized bed under dry airflow and allowing 20 the powdery substance to flow.
Step (B) of: spraying an aqueous suspension or an aqueous solution which consists of water and ingredients of the water dispersible granule including at least one of the water-soluble agrochemical 25 active substance or at least one of the water-soluble solid carrier, wherein said ingredients are other than the ingredient (s) contained in the powdery substance of step (A), into the fluidized bed under dry airflow.
The present fluidized bed granulation method comprises a 30 step of charging the present powdery substance into a fluidized bed under dry airflow, that is, into a fluidized bed in which a dry gas is flowing; and allowing the present powdery substance to flow (step (A) ) , and a step of spraying the present aqueous liquid (step (B)).
13
In the present fluidized bed granulation method, the step (B) may be carried out after the step (A), or the step (A) and the step (B) may be simultaneously carried out.
Examples of the gas which is allowed to flow in a fluidized 5 bed for the present fluidized bed granulation method include air and a nitrogen gas.
The dry gas which is allowed to flow in a fluidized bed is usually obtained by heating a gas. The temperature of the dry gas which is allowed to flow in a fluidized bed is usually 40 to 10 200°C at a gas inlet portion provided to the fluidized bed. The temperature of the dry gas can be appropriately adjusted depending on physical properties and quality required for the water dispersible granule of the present invention as well as physical properties such as the melting point of the present 15 powdery substance used in the present fluidized bed granulation method. The flow rate of the dry gas is appropriately adjusted depending on fluidity of the present powdery substance and the water dispersible granule of the present invention as well as physical properties and quality required for the water 20 dispersible granule of the present invention.
There is no particular limitation on a spraying position of the present aqueous liquid in a fluidized bed as long as it is possible to spray the present aqueous liquid into the fluidized bed. The present aqueous liquid can be sprayed from one or more 25 positions.
The present fluidized bed granulation method can be carried out by a batch-wise method or a continuous method. According to the present fluidized bed granulation method, the present aqueous liquid may be sprayed in the direction opposite to the 30 flow direction of a gas at a gas inlet portion provided to a fluidized bed, or the present aqueous liquid may be sprayed in the same direction as the flow direction of a gas at a gas inlet portion provided to a fluidized bed. An example of the present fluidized bed granulation method includes a method which 35 comprises blowing a gas upward in a fluidized bed from a gas inlet portion provided to a lower portion of the fluidized bed, 14 and at the same time, spraying the present aqueous liquid upward from a lower portion of the fluidized bed.
In the case of using a batch-wise method as the present fluidized bed granulation method, the amount of the water 5 dispersible granule of the present invention produced in a batch is appropriately selected depending on ingredients of the water dispersible granule of the present invention, the kind of a fluidized bed granulator, and the like. In the case of using a continuous method as the present fluidized bed granulation 10 method, the amount of the water dispersible granule of the present invention produced per unit time is appropriately selected depending on ingredients of the water dispersible granule of the present invention, the kind of a fluidized bed granulator, and the like. For example, when the present 15 fluidized bed granulation method is carried out using STREA-1, GPCG-3 or Procell 5, the production amount is usually about 300 g to 5 kg, preferably about 500 g to 3 kg in the case of a batch-type method, and the production amount is usually about 1 kg to 5 kg/hr, preferably about 1.5 kg to 3.5 kg/hr in the case 20 of a continuous method.
A quantitative ratio of the water-soluble agrochemical active substance which has a water solubility of 100 ppm or more at 20°C and is solid at 20°C, the surfactant, and the water-soluble solid carrier which is solid at 20°C used in the present 25 fluidized bed granulation method is appropriately determined depending on the desired inclusion of the water dispersible granule of the present invention. For the inclusion of the water dispersible granule of the present invention, usually, 100 parts by weight of the water-soluble agrochemical active 30 substance which has a water solubility of 100 ppm or more at 20°C and is solid at 20°C, about 3 to 200 parts by weight of the surfactant, and about 12 to 800 parts by weight of the water-soluble solid carrier which is solid at 20°C are used.
The present fluidized bed granulation method can be carried 35 out under various production conditions adjusted appropriately.
15
The present fluidized bed granulation method is usually carried out at 20 to 100°C in a fluidized bed upon fluidized bed granulation and at a relative humidity of 30 to 80% in a fluidized bed.
5 Granules produced by the present fluidized bed granulation method as described above may be directly used as the water dispersible granule of the present invention. Alternatively, granules produced by the present fluidized bed granulation method as described above may be sieved to obtain granules 10 having the desired size with less variation in particle size, and the obtained granules can be used as the water dispersible granule of the present invention.
Examples of the water dispersible granule of the present invention include a preparation which has a high content of 15 granules having a size of 200 to 1,800 pm sieved by dry sieving, a preparation which has an apparent specific gravity of 0.2 to 1.0 g/ml, and a preparation which has 0.3 to 0.9 g/ml.
The water dispersible granule of the present invention is used for control of pests or regulation of plant growth 20 depending on the agrochemical active substance contained in the water dispersible granule. When the agrochemical active substance contained in the water dispersible granule of the present invention is an insecticidal compound, the water dispersible granule of the present invention can be used, for 25 example, as an insecticide for vegetables or fruit trees.
For example, the water dispersible granule of the present invention is diluted with water and then applied to crops, soil or the like with a sprayer and so on. The water dispersible granule of the present invention is usually 10 to 10,000-fold 30 diluted with water, although the dilution rate varies depending on the kind or amount of the agrochemical active substance contained in the water dispersible granule of the present invention as well as the kind of a subject pest and an application scene.
35 Depending on the solid carrier used in the water dispersible granule of the present invention, even when a water 16 dilution of the water dispersible granule of the present invention is directly sprayed over fruit trees or vegetables, the surfaces of fruits and so on are less stained. Therefore, when the agrochemical active substance contained in the water 5 dispersible granule of the present invention is an insecticidal compound and the solid carrier used is suitable, the water dispersible granule of the present invention is suited for control of pests which cause feeding damage of fruits or vegetables. Examples of such fruit trees and vegetables include 10 pear, apple, cherry, peach, grape, citrus fruits, persimmon, cucumber, watermelon, melon, tomato and green pepper.
The water dispersible granule of the present invention can be packaged in a container conventionally used for packaging of a granule or a wettable powder, such as an aluminum bag, a paper 15 bag, a paper pack, or a polyethylene bottle. In order to avoid moisture absorption during storage, a polyethylene bottle, an aluminum bag, a paper bag having an aluminum lining, and a plastic bag are preferred. For prevention of moisture absorption during storage, improvement in safety and improvement 20 in usability upon dilution, the water dispersible granule of the present invention can be packaged in a water-soluble pack and then put in the above-described container.
Examples 25 The present invention will be described in detail by way of the following examples to which the present invention is not limited.
Example 1 30 48 parts by weight of clothianidin, 3 parts by weight of NEWKALGEN WG-4 (trade name; sodium lignin sulfonate, TAKEMOTO OIL & FAT Co., Ltd.), 0.1 part by weight of butylparabene (butyl p-hydroxybenzoate, Yoshitomi Fine Chemicals, Ltd.), 0.3 part by weight of ANTIFOAM E-20 (trade name; silicone emulsion, Kao 35 Corporation) and 48.6 parts by weight of ion-exchange water were mixed and then wet-ground using Dyno Mill KDL-1.5 (trade name) 17 to obtain a clothianidin suspension having a volume median diameter of about 1.6 pm (hereinafter, sometimes, referred to as the clothianidin suspension). To 100 parts by weight of the suspension, 5 parts by weight of sodium hydrogen carbonate 5 (Solvey), 5 parts by weight of urea (BASF), 0.2 part by weight of ANTIFOAM E-20, 0.3 part by weight of Cyanine Green and 5 parts by weight of NEWKALGEN WG-2 (trade name; naphthalenesulfonic acid formaldehyde condensate sodium salt, TAKEMOTO OIL & FAT Co., Ltd.) were added, followed by stirring 10 and mixing well using a propeller stirrer to obtain a spray slurry. Then, 115.5 parts by weight of the spray slurry was sprayed through a two-fluid nozzle into a bed in which 33.1 parts by weight of Glucidex 1 (trade name; dextrin, ROQUETT) was allowed to flow, granulated and dried by using Procell 5 (trade 15 name; Glatt) as a fluidized bed granulator. The granules thus obtained were sieved to obtain the water dispersible granule of the present invention containing 48% by weight of clothianidin. Granulation conditions and sieving conditions are as follows. Supplied hot air temperature: 100°C 20 Spraying pressure: 2.0 atm.
Hot air blowing-in direction: upward direction
Spraying direction: upward direction
Mixed slurry delivery speed: about 50 ml/min.
Relative humidity in bed: 40 to 60% 25 Sieving range after granulation and drying: 300 to 1,700 pm
Example 2
To 100 parts by weight of the clothianidin suspension described in Example 1, 5 parts by weight of sodium hydrogen 30 carbonate, 7 parts by weight of urea, 0.2 part by weight of ANTIFOAM E-20, 0.3 part by weight of Cyanine Green and 5 parts by weight of NEWKALGEN WG-2 were added, followed by stirring and mixing well using a propeller stirrer to obtain a spray slurry. Then, 117.5 parts by weight of the spray slurry was sprayed 35 through a two-fluid nozzle into a bed in which 31.1 parts by weight of Glucidex 1 was allowed to flow, granulated and dried 18 by using Procell 5 as a fluidized bed granulator. The granules thus obtained were sieved to obtain the water dispersible granule of the present invention containing 48% by weight of clothianidin. Granulation conditions and sieving conditions are 5 as follows.
Supplied hot air temperature: 100°C Spraying pressure: 2.0 atm.
Hot air blowing-in direction: upward direction Spraying direction: upward direction 10 Mixed slurry delivery speed: about 50 ml/min.
Relative humidity in bed: 40 to 60%
Sieving range after granulation and drying: 300 to 1,700 pm Example 3 15 To 100 parts by weight of the clothianidin suspension described in Example 1, 5 parts by weight of sodium hydrogen carbonate, 7 parts by weight of urea, 0.2 part by weight of ANTIFOAM E-20, 0.3 part by weight of Cyanine Green, 5 parts by weight of NEWKALGEN WG-2 and 8.5 parts by weight of Arabiccol SS 20 (trade name; gum arabic, San-ei Yakuhin Boeki Co., Ltd.) were added, followed by stirring and mixing well using a propeller stirrer to obtain a spray slurry. Then, 126.0 parts by weight of the spray slurry was sprayed through a two-fluid nozzle into a bed in which 22.6 parts by weight of Glucidex 1 was allowed to 25 flow, granulated and dried by using Procell 5 as a fluidized bed granulator. The granules thus obtained were sieved to obtain the water dispersible granule of the present invention containing . 48% by weight of clothianidin. Granulation conditions and sieving conditions are as follows.
30 Supplied hot air temperature: 100°C Spraying pressure: 2.0 atm.
Hot air blowing-in direction: upward direction
Spraying direction: upward direction
Mixed slurry delivery speed: about 50 ml/min.
35 Relative humidity in bed: 40 to 60%
Sieving range after granulation and drying: 300 to 1,700 pm 19
Example 4
To 100 parts by weight of the clothianidin suspension described in Example 1, 5 parts by weight of sodium hydrogen 5 carbonate, 9 parts by weight of urea, 0.2 part by weight of ANTIFOAM E-20, 0.3 part by weight of Cyanine Green, 5 parts by weight of NEWKALGEN WG-2 and 8.5 parts by weight of Arabiccol SS were added, followed by stirring and mixing well using a propeller stirrer to obtain a spray slurry. Then, 128.0 parts 10 by weight of the spray slurry was sprayed through a two-fluid nozzle into a bed in which 20.6 parts by weight of Glucidex 1 was allowed to flow, granulated and dried by using Procell 5 as a fluidized bed granulator. The granules thus obtained were sieved to obtain the water dispersible granule of the present 15 invention containing 48% by weight of clothianidin. Granulation conditions and sieving conditions are as follows.
Supplied hot air temperature: 100°C Spraying pressure: 2.0 atm.
Hot air blowing-in direction: upward direction 20 Spraying direction: upward direction
Mixed slurry delivery speed: about 50 ml/min.
Relative humidity in bed: 40 to 60%
Sieving range after granulation and drying: 300 to 1,700 pm 25 Example 5
To 100 parts by weight of the clothianidin suspension described in Example 1, 5 parts by weight of sodium hydrogen carbonate, 3 parts by weight of urea, 0.2 part by weight of ANTIFOAM E-20, 0.3 part by weight of Cyanine Green and 5 parts 30 by weight of NEWKALGEN WG-2 were added, followed by stirring and mixing well using a propeller stirrer to obtain a spray slurry. Then, 113.5 parts by weight of the spray slurry was sprayed through a two-fluid nozzle into a bed in which 35.1 parts by weight of Glucidex 1 was allowed to flow, granulated and dried 35 by using STREA-1 (trade name; Powrex Corporation) as a fluidized bed granulator. The granules thus obtained were sieved to 20 obtain the water dispersible granule of the present invention containing 48% by weight of clothianidin. Granulation conditions and sieving conditions are as follows.
Supplied hot air temperature: 60°C 5 Spraying pressure: 0.6 atm.
Hot air blowing-in direction: upward direction
Spraying direction: downward direction
Mixed slurry delivery speed: about 10 to 20 ml/min.
Sieving range after granulation and drying: 300 to 1,700 pm 10
Example 6
To 100 parts by weight of the clothianidin suspension described in Example 1, 5 parts by weight of sodium hydrogen carbonate, 5 parts by weight of urea, 0.2 part by weight of 15 ANTIFOAM E-20, 0.3 part by weight of Cyanine Green and 5 parts by weight of NEWKALGEN WG-2 were added, followed by stirring and mixing well using a propeller stirrer to obtain a spray slurry. Then, 115.5 parts by weight of the spray slurry was sprayed through a two-fluid nozzle into a bed in which 33.1 parts by 20 weight of Glucidex 1 was allowed to flow, granulated and dried by using STREA-1 as a fluidized bed granulator. The granules thus obtained were sieved to obtain the water dispersible granule of the present invention containing 48% by weight of clothianidin. Granulation conditions and sieving conditions are 25 as follows.
Supplied hot air temperature: 60°C Spraying pressure: 0.6 atm.
Hot air blowing-in direction: upward direction Spraying direction: downward direction 30 Mixed slurry delivery speed: about 10 to 20 ml/min.
Sieving range after granulation and drying: 300 to 1,700 pm
Example 7
To 100 parts by weight of the clothianidin suspension 35 described in Example 1, 5 parts by weight of sodium hydrogen carbonate, 7 parts by weight of urea, 0.2 part by weight of 21 ANTIFOAM E-20, 0.3 part by weight of Cyanine Green and 5 parts by weight of NEWKALGEN WG-2 were added, followed by stirring and mixing well using a propeller stirrer to obtain a spray slurry. Then, 117.5 parts by weight of the spray slurry was sprayed 5 through a two-fluid nozzle into a bed in which 31.1 parts by weight of Glucidex 1 was allowed to flow, granulated and dried by using STREA-1 as a fluidized bed granulator. The granules thus obtained were sieved to obtain the water dispersible granule of the present invention containing 48% by weight of 10 clothianidin. Granulation conditions and sieving conditions are as follows.
Supplied hot air temperature: 60°C Spraying pressure: 0.6 atm.
Hot air blowing-in direction: upward direction 15 Spraying direction: downward direction
Mixed slurry delivery speed: about 10 to 20 ml/min.
Sieving range after granulation and drying: 300 to 1,700 pm
Example 8 20 To 100 parts by weight of the clothianidin suspension described in Example 1, 5 parts by weight of sodium hydrogen carbonate, 7 parts by weight of urea, 0.2 part by weight of ANTIFOAM E-20, 0.3 part by weight of Cyanine Green, 5 parts by weight of NEWKALGEN WG-2 and 8.5 parts by weight of gum arabic 25 were added, followed by stirring and mixing well using a propeller stirrer to obtain a spray slurry. Then, 126.0 parts by weight of the spray slurry was sprayed through a two-fluid nozzle into a bed in which 22.6 parts by weight of Glucidex 1 was allowed to flow, granulated and dried by using STREA-1 as a 30 fluidized bed granulator. The granules thus obtained were sieved to obtain the water dispersible granule of the present invention containing 48% by weight of clothianidin. Granulation conditions and sieving conditions are as follows.
Supplied hot air temperature: 60°C 35 Spraying pressure: 0.6 atm.
Hot air blowing-in direction: upward direction 22
Spraying direction: downward direction
Mixed slurry delivery speed: about 10 to 20 ml/min.
Sieving range after granulation and drying: 300 to 1,700 pm 5 Example 9
To 100 parts by weight of the clothianidin suspension described in Example 1, 5 parts by weight of sodium hydrogen carbonate, 5 parts by weight of urea, 0.2 part by weight of ANTIFOAM E-20, 0.3 part by weight of Cyanine Green, 5 parts by 10 weight of NEWKALGEN WG-2 and 8.5 parts by weight of gum arabic were added, followed by stirring and mixing well using a propeller stirrer to obtain a spray slurry. Then, 124.0 parts by weight of the spray slurry was sprayed through a two-fluid nozzle into a bed in which 24.6 parts by weight of Dextrin MF30 15 (trade name; dextrin, NIPPON STARCH CHEMICAL CO., LTD.) was allowed to flow, granulated and dried by using STREA-1 as a fluidized bed granulator. The granules thus obtained were sieved to obtain the water dispersible granule of the present invention containing 48% by weight of clothianidin. Granulation 20 conditions and sieving conditions are as follows.
Supplied hot air temperature: 60°C Spraying pressure: 0.6 atm.
Hot air blowing-in direction: upward direction Spraying direction: downward direction 25 Mixed slurry delivery speed: about 10 to 20 ml/min.
Sieving range after granulation and drying: 300 to 1,700 pm
Example 10
To 100 parts by weight of the clothianidin suspension 30 described in Example 1, 5 parts by weight of sodium hydrogen carbonate, 0.2 part by weight of ANTIFOAM E-20, 0.5 part by weight of Cyanine Green and 5 parts by weight of Geropon SC/213 (trade name; potassium polycarboxylate, Rhodia) were added, followed by stirring and mixing well using a propeller stirrer 35 to obtain a spray slurry. Then, 110.7 parts by weight of the spray slurry was sprayed through a two-fluid nozzle into a bed 23 in which 5 parts by weight of Arabiccol SS and 32.9 parts by weight of Dextrin MF30 were allowed to flow, granulated and dried by using GPCG-3 (trade name; Glatt) as a fluidized bed granulator. The granules thus obtained were sieved to obtain 5 the water dispersible granule of the present invention containing 48% by weight of clothianidin. Granulation conditions and sieving conditions are as follows.
Supplied hot air temperature: 100°C Spraying pressure: 2.5 atm.
10 Hot air blowing-in direction: upward direction Spraying direction: downward direction Mixed slurry delivery speed: 29 to 73 g/min.
Sieving range after granulation and drying: 300 to 1,800 pm 15 Example 11
To 100 parts by weight of the clothianidin suspension described in Example 1, 5 parts by weight of sodium hydrogen carbonate, 0.2 part by weight of ANTIFOAM E-20 and 0.5 part by weight of Cyanine Green were added, followed by stirring and 20 mixing well using a propeller stirrer to obtain a spray slurry. Then, 105.7 parts by weight of the spray slurry was sprayed through a two-fluid nozzle into a bed in which 5 parts by weight of Arabiccol SS, 5 parts by weight of NEWKALGEN WG-2 and 32.9 parts by weight of Dextrin MF30 were allowed to flow, granulated 25 and dried by using GPCC-3 as a fluidized bed granulator. The granules thus obtained were sieved to obtain the water dispersible granule of the present invention containing 48% by weight of clothianidin. Granulation conditions and sieving conditions are as follows.
30 Supplied hot air temperature: 100°C Spraying pressure: 2.5 atm.
Hot air blowing-in direction: upward direction Spraying direction: downward direction Mixed slurry delivery speed: 49 to 69 g/min.
35 Sieving range after granulation and drying: 300 to 1,800 pm 24
Example 12
To 100 parts by weight of the clothianidin suspension described in Example 1, 5 parts by weight of sodium hydrogen carbonate, 3.5 parts by weight of Arabiccol SS, 0.2 part by 5 weight of ANTIFOAM E-20 and 0.5 part by weight of Cyanine Green were added, followed by stirring and mixing well using a propeller stirrer to obtain a spray slurry. Then, 109.2 parts by weight of the spray slurry was sprayed through a two-fluid nozzle into a bed in which 5 parts by weight of Arabiccol SS, 5 10 parts by weight of NEWKALGEN WG-2 and 29.4 parts by weight of Dextrin MF30 were allowed to flow, granulated and dried by using GPCG-3 as a fluidized bed granulator. The granules thus obtained were sieved to obtain the water dispersible granule of the present invention containing 48% by weight of clothianidin. 15 Granulation conditions and sieving conditions are as follows. Supplied hot air temperature: 100°C Spraying pressure: 2.5 atm.
Hot air blowing-in direction: upward direction Spraying direction: downward direction 20 Mixed slurry delivery speed: 51 to 73 g/min.
Sieving range after granulation and drying: 300 to 1,800 pm
Example 13
To 100 parts by weight of the clothianidin suspension 25 described in Example 1, 5 parts by weight of sodium hydrogen carbonate, 3.5 parts by weight of Arabiccol SS, 0.2 part by weight of ANTIFOAM E-20, 0.5 part by weight of Cyanine Green and 1 part by weight of PVP K30 (polyvinyl pyrrolidone, BASF) were added, followed by stirring and mixing well using a propeller 30 stirrer to obtain a spray slurry. Then, 110.2 parts by weight of the spray slurry was sprayed through a two-fluid nozzle into a bed in which 5 parts- by weight of Arabiccol SS, 5 parts by weight of NEWKALGEN WG-2 and 28.4 parts by weight of Dextrin MF30 were allowed to flow, granulated and dried by using GPCG-3 35 as a fluidized bed granulator. The granules thus obtained were sieved to obtain the water dispersible granule of the present 25 invention containing 48% by weight of clothianidin. Granulation conditions and sieving conditions are as follows.
Supplied hot air temperature: 100°C Spraying pressure: 2.5 atm.
5 Hot air blowing-in direction: upward direction Spraying direction: downward direction Mixed slurry delivery speed: 49 to 69 g/min.
Sieving range after granulation and drying: 300 to 1,800 pm 10 Example 14
To 100 parts by weight of the clothianidin suspension described in Example 1, 5 parts by weight of sodium hydrogen carbonate, 3.5 parts by weight of Arabiccol SS, 0.2 part by weight of ANTIFOAM E-20 and 0.5 part by weight of Cyanine Green 15 were added, followed by stirring and mixing well using a propeller stirrer to obtain a spray slurry. Then, 109.2 parts by weight of the spray slurry was sprayed through a two-fluid nozzle into a bed in which 5 parts by weight of Arabiccol SS, 5 parts by weight of NEWKALGEN WG-2 and 29.4 parts by weight of 20 Dextrin NDS (trade name; dextrin, NIPPON STARCH CHEMICAL CO., LTD.) were allowed to flow, granulated and dried by using GPCG-3 as a fluidized bed granulator. The granules thus obtained were sieved to obtain the water dispersible granule of the present invention containing 48% by weight of clothianidin. Granulation 25 conditions and sieving conditions are as follows.
Supplied hot air temperature: 100°C Spraying pressure: 2.5 atm.
Hot air blowing-in direction: upward direction Spraying direction: downward direction 30 Mixed slurry delivery speed: 49 to 79 g/min.
Sieving range after granulation and drying: 300 to 1,800 pm
Example 15
To 100 parts by weight of the clothianidin suspension 35 described in Example 1, 5 parts by weight of sodium hydrogen carbonate, 3.5 parts by weight of Arabiccol SS, 10 parts by 26 weight of urea, 0.2 part by weight of ANTIFOAM E-20 and 0.5 part by weight of Cyanine Green were added, followed by stirring and mixing well using a propeller stirrer to obtain a spray slurry. Then, 119.2 parts by weight of the spray slurry was sprayed 5 through a two-fluid nozzle into a bed in which 5 parts by weight of Arabiccol SS, 5 parts by weight of NEWKALGEN WG-2 and 19.4 parts by weight of Dextrin MF30 were allowed to flow, granulated and dried by using GPCG-3 as a fluidized bed granulator. The granules thus obtained were sieved to obtain the water 10 dispersible granule of the present invention containing 48% by weight of clothianidin. Granulation conditions and sieving conditions are as follows.
Supplied hot air temperature: 100°C Spraying pressure: 2.5 atm.
15 Hot air blowing-in direction: upward direction Spraying direction: downward direction Mixed slurry delivery speed: 31 to 63 g/min.
Sieving range after granulation and drying: 300 to 1,800 pm 20 Example 16
To 100 parts by weight of the clothianidin suspension described in Example 1, 5 parts by weight of sodium hydrogen carbonate, 3.5 parts by weight of Arabiccol SS, 7 parts by weigh of urea and 0.2 part by weight of ANTIFOAM E-20 were added, 25 followed by stirring and mixing well using a propeller stirrer to obtain a spray slurry. Then, while a powder mixture of 5 parts by weight of Arabiccol SS, 5 parts by weight of NEWKALGEN WG-2, 22.6 parts by weight of Glucidex 1 and 0.3 part by weight of Cyanine Green was continuously charged into a bed and was 30 allowed to flow therein, 115.7 parts by weight of the spray slurry was continuously sprayed into the bed through a two-fluid nozzle, granulated and dried by using Procell 5 as a fluidized bed granulator. The granules thus obtained were sieved to obtain the water dispersible granule of the present invention 35 containing 48% by weight of clothianidin. Granulation conditions and sieving conditions are as follows.
27
Supplied hot air temperature: 90 to 95°C Spraying pressure: 2.0 atm.
Hot air blowing-in direction: upward direction Spraying direction: upward direction 5 Mixed powder charging speed: about 15 g/min.
Mixed slurry delivery speed: about 54 g/min.
Sieving range after granulation and drying: 300 to 1,800 pm
Example 17 10 To 100 parts by weight of the clothianidin suspension described in Example 1, 5 parts by weight of sodium hydrogen carbonate, 3.5 parts by weight of Arabiccol SS, 0.2 part by weight of ANTIFOAM E-20 and 0.3 part by weight of Cyanine Green were added, followed by stirring and mixing well using a 15 propeller stirrer to obtain a spray slurry. Then, while a powder mixture of 5 parts by weight of Arabiccol SS, 5 parts by weight of NEWKALGEN WG-2, 7 parts by weight of urea and 22.6 parts by weight of Glucidex 1 was continuously charged into a bed and was allowed to flow therein, 109.0 parts by weight of 20 the spray slurry was continuously sprayed into the bed through a two-fluid nozzle, granulated and dried by using Procell 5 as a fluidized bed granulator. The granules thus obtained were sieved to obtain the water dispersible granule of the present invention containing 48% by weight of clothianidin. Granulation 25 conditions and sieving conditions are as follows.
Supplied hot air temperature: 90°C Spraying pressure: 2.0 atm.
Hot air blowing-in direction: upward direction Spraying direction: upward direction 30 Mixed powder charging speed: about 16 g/min.
Mixed slurry delivery speed: about 43 g/min.
Sieving range after granulation and drying: 300 to 1,800 pm
Example 18 35 To 100 parts by weight of the clothianidin suspension described in Example 1, 5 parts by weight of sodium hydrogen 28 carbonate, 0.2 part by weight of ANTIFOAM E-20, 0.3 part by weight of Cyanine Green, 7 parts by weight of urea and 5 parts by weight of NEWKALGEN WG-2 were added, followed by stirring and mixing well using a propeller stirrer to obtain a spray slurry.
5 Then, while a powder mixture of 8.5 parts by weight of Arabiccol SS and 22.6 parts by weight of Glucidex 1 was continuously charged into a bed and was allowed to flow therein, 117.5 parts by weight of the spray slurry was continuously sprayed into the bed through a two-fluid nozzle, granulated and dried by using 10 Procell 5 as a fluidized bed granulator. The granules thus obtained were sieved to obtain the water dispersible granule of the present invention containing 48% by weight of clothianidin. Granulation conditions and sieving conditions are as follows. Supplied hot air temperature: 95°C 15 Spraying pressure: 2.0 atm.
Hot air blowing-in direction: upward direction
Spraying direction: upward direction
Mixed powder charging speed: about 11 g/min.
Mixed slurry delivery speed: about 43 g/min.
20 Sieving range after granulation and drying: 300 to 1,800 pm
Example 19
To 100 parts by weight of the clothianidin suspension described in Example 1, 5 parts by weight of sodium hydrogen
25 carbonate and 0.2 part by weight of ANTIFOAM E-20 were added, followed by stirring and mixing well using a propeller stirrer to obtain a spray slurry. Then, while a powder mixture of 8.5 parts by weight of Arabiccol SS, 0.3 part by weight of Cyanine Green, 7 parts by weight of urea, 5 parts by weight of NEWKALGEN
30 WG-2 and 22.6 parts by weight of Glucidex 1 was continuously charged into a bed and was allowed to flow therein, 105.2 parts by weight of the spray slurry was continuously sprayed into the bed through a two-fluid nozzle, granulated and dried by using Procell 5 as a fluidized bed granulator. The granules thus 35 obtained were sieved to obtain the water dispersible granule of 29 the present invention containing 48% by weight of clothianidin. Granulation conditions and sieving conditions are as follows. Supplied hot air temperature: 92°C Spraying pressure: 2.0 atm.
5 Hot air blowing-in direction: upward direction Spraying direction: upward direction Mixed powder charging speed: about 17 g/min.
Mixed slurry delivery speed: about 45 g/min.
Sieving range after granulation and drying: 300 to 1,800 pm 10
Example 20
To 100 parts by weight of the clothianidin suspension described in Example 1, 5 parts by weight of sodium hydrogen carbonate, 0.2 part by weight of ANTIFOAM E-20, 0.3 part by 15 weight of Cyanine Green and 5 parts by weight of NEWKALGEN WG-2 were added, followed by stirring and mixing well using a propeller stirrer to obtain a spray slurry. Then, while a powder mixture of 8.5 parts by weight of Arabiccol SS and 29.6 parts by weight of Glucidex 1 was continuously charged into a 20 bed and was allowed to flow therein, 110.5 parts by weight of the spray slurry was continuously sprayed into the bed through a two-fluid nozzle, granulated and dried by using Procell 5 as a fluidized bed granulator. The granules thus obtained were sieved to obtain the water dispersible granule of the present 25 invention containing 48% by weight of clothianidin. Granulation conditions and sieving conditions are as follows.
Supplied hot air temperature: 95°C Spraying pressure: 2.0 atm.
Hot air blowing-in direction: upward direction 30 Spraying direction: upward direction
Mixed powder charging speed: about 15 g/min.
Mixed slurry delivery speed: about 44 g/min.
Sieving range after granulation and drying: 300 to 1,800 pro 35 Example 21 30
To 100 parts by weight of the clothianidin suspension described in Example 1, 5 parts by weight of sodium hydrogen carbonate, 0.2 part by weight of ANTIFOAM E-20, 0.3 part by weight of Cyanine Green and 5 parts by weight of NEWKALGEN WG-2 5 were added, followed by stirring and mixing well using a propeller stirrer to obtain a spray slurry. Then, while a powder of 38.1 parts by weight of Glucidex 1 was continuously charged into a bed and was allowed to flow therein, 110.5 parts by weight of the spray slurry was continuously sprayed into the 10 bed through a two-fluid nozzle, granulated and dried by using Procell 5 as a fluidized bed granulator. The granules thus obtained were sieved to obtain the water dispersible granule of the present invention containing 48% by weight of clothianidin. Granulation conditions and sieving conditions are as follows.
15 Supplied hot air temperature: 95°C Spraying pressure: 2.0 atm.
Hot air blowing-in direction: upward direction
Spraying direction: upward direction
Mixed powder charging speed: about 15 g/min.
20 Mixed slurry delivery speed: about 46 g/min.
Sieving range after granulation and drying: 300 to 1,800 pm
Example 22
To 100 parts by weight of the clothianidin suspension 25 described in Example 1, 5 parts by weight of sodium hydrogen carbonate, 3.5 parts by weight of Arabiccol SS, 7 parts by weight of urea, 0.2 part by weight of ANTIFOAM E-20 and 0.3 part by weight of Cyanine Green were added, followed by stirring and mixing well using a propeller stirrer to obtain a spray slurry. 30 Then, while a powder mixture of 5 parts by weight of Arabiccol SS, 5 parts by weight of NEWKALGEN WG-2 and 22.6 parts by weight of Glucidex 1 was continuously charged into a bed and was allowed to flow therein, 116.0 parts by weight of the spray slurry was continuously sprayed into the bed through a two-fluid 35 nozzle, granulated and dried by using Procell 5 as a fluidized bed granulator. The granules thus obtained were sieved to 31 obtain the water dispersible granule of the present invention containing 48% by weight of clothianidin. Granulation conditions and sieving conditions are as follows.
Supplied hot air temperature: 98°C 5 Spraying pressure: 2.0 atm.
Hot air blowing-in direction: upward direction
Spraying direction: upward direction
Mixed powder charging speed: about 15 g/min.
Mixed slurry delivery speed: about 54 g/min.
10 Sieving range after granulation and drying: 300 to 1,800 pm
Example 23
To 100 parts by weight of the clothianidin suspension described in Example 1, 5 parts by weight of sodium hydrogen 15 carbonate, 5 parts by weight of NEWKALGEN WG-2, 3 parts by weight of urea, 0.2 part by weight of ANTIFOAM E-20 and 0.3 part by weight of Cyanine Green were added, followed by stirring and mixing well using a propeller stirrer to obtain a spray slurry. Then, while 35.1 parts by weight of Glucidex 1 was continuously 20 charged into a bed and was allowed to flow therein, 113.5 parts by weight of the spray slurry was continuously sprayed into the bed through a two-fluid nozzle, granulated and dried by using Procell 5 as a fluidized bed granulator. The granules thus obtained were sieved to obtain the water dispersible granule of 25 the present invention containing 48% by weight of clothianidin. Granulation conditions and sieving conditions are as follows. Supplied hot air temperature: 95°C Spraying pressure: 2.0 atm.
Hot air blowing-in direction: upward direction 30 Spraying direction: upward direction
Mixed powder charging speed: about 15 g/min.
Mixed slurry delivery speed: about 46 g/min.
Sieving range after granulation and drying: 300 to 1,800 pm 35 Example 24 32
To 100 parts by weight of the clothianidin suspension described in Example 1, 5 parts by weight of sodium hydrogen carbonate, 5 parts by weight of NEWKALGEN WG-2, 3 parts by weight of Glucidex 1, 0.2 part by weight of ANTIFOAM E-20 and 5 0.3 part by weight of Cyanine Green were added, followed by stirring and mixing well using a propeller stirrer to obtain a spray slurry. Then, while 35.1 parts by weight of Glucidex 1 was continuously charged into a bed and was allowed to flow therein, 113.5 parts by weight of the spray slurry was 10 continuously sprayed into the bed through a two-fluid nozzle, granulated and dried by using Procell 5 as a fluidized bed granulator. The granules thus obtained were sieved to obtain the water dispersible granule of the present invention containing 48% by weight of clothianidin. Granulation 15 conditions and sieving conditions are as follows.
Supplied hot air temperature: 95°C Spraying pressure: 2.0 atm.
Hot air blowing-in direction: upward direction Spraying direction: upward direction 20 Mixed powder charging speed: about 13 g/min.
Mixed slurry delivery speed: about 42 g/min.
Sieving range after granulation and drying: 300 to 1,800 pm
Comparative Example 1 25 48 parts by weight of clothianidin, 3 parts by weight of NEWKALGEN WG-4, 5 parts by weight of NEWKALGEN WG-2, 5 parts by weight of sodium hydrogen carbonate and 35.7 parts by weight of Glucidex 1 were mixed and ground with a mortar. To 96.7 parts by weight of the powder mixture, an aqueous solution consisting 30 of 10 parts by weight of water, 0.3 part by weight of Cyanine Green and 3 parts by weight of urea was added, followed by kneading with a mortar. Then, the kneaded mixture was extruded and granulated by using a single dome granulator (DALTON) . The granules thus obtained were dried in a fluidized bed at 60°C for 35 30 minutes to obtain a water dispersible granule containing 48% by weight of clothianidin.
33
Comparative Example 2
To 100 parts by weight of the clothianidin suspension described in Example 1, 5 parts by weight of sodium hydrogen 5 carbonate, 7 parts by weight of urea, 0.2 part by weight of ANTIFOAM E-20, 0.3 part by weight of Cyanine Green, 5 parts by weight of NEWKALGEN WG-2 and 8.5 parts by weight of Arabiccol SS were added, followed by stirring and mixing well using a propeller stirrer to obtain a spray slurry. Then, 126.0 parts 10 by weight of the spray slurry was sprayed through a two-fluid nozzle into a bed in which 22.6 parts by weight of Argirec B22 (trade name; kaolin clay, AGS) was allowed to flow, granulated and dried by using STREA-1 as a fluidized bed granulator. The granules thus obtained were sieved to obtain a water dispersible 15 granule containing 48% by weight of clothianidin. Granulation conditions and sieving conditions are as follows.
Supplied hot air temperature: 60°C Spraying pressure: 0.6 atm.
Hot air blowing-in direction: upward direction 20 Spraying direction: downward direction
Mixed slurry delivery speed: about 10 to 20 ml/min.
Sieving range after granulation and drying: 300 to 1,700 pm
Comparative Example 3 25 To 100 parts by weight of the clothianidin suspension described in Example 1, 5 parts by weight of sodium hydrogen carbonate, 32.9 parts by weight of urea, 0.2 part by weight of ANTIFOAM E-20, 0.5 part by weight of Cyanine Green, 5 parts by weight of NEWKALGEN WG-2 and 5 parts by weight of gum arabic 30 were added, followed by stirring and mixing well using a propeller stirrer to obtain a spray slurry. Then the spray slurry was sprayed and granulated by using GPCG-3 as a fluidized bed granulator. However, caking occurred in the bed, and therefore, a water dispersible granule could not be obtained.
35 34
Granulation conditions are as follows. Supplied hot air temperature: 100°C Spraying pressure: 3.0 atm.
Hot air blowing-in direction: upward direction 5 Spraying direction: downward direction
Mixed slurry delivery speed: 30 to 44 g/min.
Comparative Example 4
To 100 parts by weight of the clothianidin suspension 10 described in Example 1, 5 parts by weight of sodium hydrogen carbonate, 37.9 parts by weight of urea, 0.2 part by weight of ANTIFOAM E-20, 0.5 part by weight of Cyanine Green and 5 parts by weight of NEWKALGEN WG-2 were added, followed by stirring and mixing well using a propeller stirrer to obtain a spray slurry. 15 Then the spray slurry was sprayed and granulated by using GPCG-3 as a fluidized bed granulator. However, caking occurred in the bed, and therefore, a water dispersible granule could not be obtained. Granulation conditions are as follows.
Supplied hot air temperature: 100°C 20 Spraying pressure: 3.0 to 2.5 atm.
Hot air blowing-in direction: upward direction Spraying direction: downward direction Mixed slurry delivery speed: 29 to 70 g/min.
25 Comparative Example 5
To 100 parts by weight of the clothianidin suspension described in Example 1, 26.7 parts by weight of potassium dihydrogen phosphate (PRAYON), 16.2 parts by weight of urea, 0.2 part by weight of ANTIFOAM E-20, 0.5 part by weight of Cyanine 30 Green and 5 parts by weight of NEWKALGEN WG-2 were added, followed by stirring and mixing well using a propeller stirrer to obtain a spray slurry. Then the spray slurry was sprayed and granulated by using GPCG-3 as a fluidized bed granulator. However, caking occurred in the bed, and therefore, a water 35 dispersible granule could not be obtained. Granulation conditions are as follows.
35
Supplied hot air temperature: 100°C Spraying pressure: 2.5 atm.
Hot air blowing-in direction: upward direction Spraying direction: downward direction 5 Mixed slurry delivery speed: 28 to 50 g/min.
Comparative Example 6
To 100 parts by weight of the clothianidin suspension described in Example 1, 29.7 parts by weight of potassium 10 dihydrogen phosphate, 16.2 parts by weight of urea, 0.2 part by weight of ANTIFOAM E-20, 0.5 part by weight of Cyanine Green and 2 parts by weight of NEWKALGEN WG-2 were added, followed by stirring and mixing well using a propeller stirrer to obtain a spray slurry. Then the spray slurry was sprayed and granulated 15 by using GPCG-3 as a fluidized bed granulator. However, caking occurred in the bed, and therefore, a water dispersible granule could not be obtained. Granulation conditions are as follows. Supplied hot air temperature: 100°C Spraying pressure: 2.5 to 2.0 atm.
20 Hot air blowing-in direction: upward direction Spraying direction: downward direction Mixed slurry delivery speed: 28 to 63 g/min.
Comparative Example 7 25 To 100 parts by weight of the clothianidin suspension described in Example 1, 5 parts by weight of sodium hydrogen carbonate, 37.9 parts by weight of Dextrin NDS, 0.2 part by weight of ANTIFOAM E-20, 0.5 part by weight of Cyanine Green and 5 parts by weight of NEWKALGEN WG-2 were added, followed by 30 stirring and mixing well using a propeller stirrer to obtain a spray slurry. Then the spray slurry was sprayed and granulated by using GPCG-3 as a fluidized bed granulator. However, caking occurred in the bed, and therefore, a water dispersible granule could not be obtained. Granulation 35 conditions are as follows.
36
Supplied hot air temperature: 100°C Spraying pressure: 2.5 atm.
Hot air blowing-in direction: upward direction Spraying direction: downward direction 5 Mixed slurry delivery speed: 32 to 70 g/min.
Comparative Example 8
To 100 parts by weight of the clothianidin suspension described in Example 1, 5 parts by weight of sodium hydrogen 10 carbonate, 33.4 parts by weight of Dextrin NDS, 0.2 part by weight of ANTIFOAM E-20, 5 parts by weight of NEWKALGEN WG-2 and 5 parts by weight of Arabiccol SS were added, followed by stirring and mixing well using a propeller stirrer to obtain a spray slurry. Then the spray slurry was sprayed and granulated 15 by using GPCG-3 as a fluidized bed granulator. However, caking occurred in the bed, and therefore, a water dispersible granule could not be obtained. Granulation conditions are as follows. Supplied hot air temperature: 100°C Spraying pressure: 2.5 atm.
20 Hot air blowing-in direction: upward direction Spraying direction: downward direction Mixed slurry delivery speed: 32 to 57 g/min.
Comparative Example 9 25 To 100 parts by weight of the clothianidin suspension described in Example 1, 5 parts by weight of sodium hydrogen carbonate, 33.4 parts by weight of Dextrin NDS, 0.2 part by weight of ANTIFOAM E-20, 5 parts by weight of Geropon SC/213 and 5 parts by weight of Arabiccol SS were added, followed by 30 stirring and mixing well using a propeller stirrer to obtain a spray slurry. Then the spray slurry was sprayed and granulated by using GPCG-3 as a fluidized bed granulator. However, caking occurred in the bed, and therefore, a water dispersible granule could not be obtained. Granulation conditions are as follows.
35 Supplied hot air temperature: 100°C
37
Spraying pressure: 2.5 atm.
Hot air blowing-in direction: upward direction Spraying direction: downward direction Mixed slurry delivery speed: 24 to 51 g/min.
5
Comparative Example 10
To 100 parts by weight of the clothianidin suspension described in Example 1, 15 parts by weight of sodium hydrogen carbonate, 0.2 part by weight of ANTIFOAM E-20, 0.5 part by 10 weight of Cyanine Green, 5 parts by weight of Geropon SC/213, 5 parts by weight of Arabiccol SS and 22.9 parts by weight of
Borresperse NA (sodium lignin sulfonate, Borregaard) were added, followed by stirring and mixing well using a propeller stirrer to obtain a spray slurry. Then the spray slurry was sprayed and 15 granulated by using GPCG-3 as a fluidized bed granulator. However, caking occurred in the bed, and therefore, a water dispersible granule could not be obtained. Granulation conditions are as follows.
Supplied hot air temperature: 100°C 20 Spraying pressure: 1.3 to 2.5 atm.
Hot air blowing-in direction: upward direction Spraying direction: downward direction Mixed slurry delivery speed: 31 to 36 g/min.
25 Comparative Example 11
To 100 parts by weight of the clothianidin suspension described in Example 1, 15 parts by weight of sodium hydrogen carbonate, 0.2 part by weight of ANTIFOAM E-20, 0.5 part by weight of Cyanine Green, 5 parts by weight of NEWKALGEN WG-2, 10 30 parts by weight of Arabiccol SS and 17.9 parts by weight of
Borresperse NA were added, followed by stirring and mixing well using a propeller stirrer to obtain a spray slurry. Then the spray slurry was sprayed and granulated by using GPCG-3 as a fluidized bed granulator. However, caking occurred in the bed, 35 and therefore, a water dispersible granule could not be obtained. Granulation conditions are as follows.
38
Supplied hot air temperature: 100°C Spraying pressure: 2.5 atm.
Hot air blowing-in direction: upward direction Spraying direction: downward direction 5 Mixed slurry delivery speed: 32 to 57 g/min.
In Examples and Comparative Examples, Cyanine Green (pigment) was commercially available from Mitsui BASF Dyes Limited, Miike Dyes Works Ltd., or KASEIHIN SHOJI CO., LTD.
10
Table 1
Example 1 Example 2 Example 3 Example 4 Example 5 Clothianidin 48.0 48.0 48.0 48.0 48.0 NEWKALGEN WG-2 575 575 575 575 575 newkalgen wg-4 JTo 575 575 575 575 sodium hydrogen 5.0 5.0 5.0 5.0 5.0 carbonate urea 5.0 575 575 975 575
Arabiccol SS 8.5 8.5 butyl parabene 0.1 0.1 0.1 0.1 o.1 anti foam e-20 575 575 575 575 575
Cyanine Green 0.3 0.3 0.3 0.3 0.3
Glucidex 1 33.1 31.1 22.6 20.6 35.1
Dextrin MF30 granulator Procell 5 Procell 5 Procell 5 Procell 5 STREA 1
Table 2
Example 6 Example 7 Example 8 Example 9 Clothianidin 48.0 48.0 48.0 48.0 NEWKALGEN WG-2 575 575 575 575 NEWKALGEN WG-4 575 575 575 575 sodium hydrogen 5.0 5.0 5.0 5.0 carbonate urea 5.0 7.0 7.0 5.0
Arabiccol SS 8.5 8.5 butyl parabene 0.1 0.1 0.1 0.1 antifoam E-20 575 575 575 575
Cyanine Green 0.3 0.3 0.3 0.3
Glucidex 1 33.1 31.1 22.6 39
Dextrin MF30 24.6 granulator STREA 1 STREA 1 STREA 1 STREA 1
Table 3
Example 10 Example 11 Example 12 Example 13 Example 14
Clothianidin 48.0 48.0 51.0 48.0 48.0 NEWKALGEN WG-2 §70 §75 §70 §70 NEWKALGEN WG-4 §70 §70 §7Ö §70 §70
Geropon SC-213 5.0 sodium hydrogen 5.0 5.0 5.0 5.0 5.0 carbonate urea
Arabiccol SS §70 5.0 8.5 §75 ' §7§ PVP K30 Ï7Ö butyl parabene 0.1 0.1 0.1 0.1 0.1 ANTIFOAM E-20 0.5 Ö7§ Ö7§ Ö7§ Ö7§
Cyanine Green 0.5 0.5 0.5 0.5 0.5
Glucidex 1
Dextrin MF30 32.9 32.9 29.4 28.4
Dextrin NDS 29.4 granulator GPCG-3 GPCG-3 GPCG-3 ' GPCG-3 GPCG-3 5 Table 4
Example 15 Example 16 Example 17 Example 18
Clothianidin 48.0 48.0 48.0 48.0 NEWKALGEN WG-2 §70 5.0 ~~ §70 §70 NEWKALGEN WG-4 §70 §70 §75 §70 ~
Geropon SC-213 sodium hydrogen 5.0 5.0 5.0 5.0 carbonate urea 10.0 775 770 770
Arabiccol SS §7§ §7§ §7§ §77 PVP K30 butyl parabene 0.1 0.1 0.1 0.1 ANTIFOAM E-20 Ö7§ Ö77 Ö7§ 07§
Cyanine Green 0.5 0.3 0.3 0.3
Glucidex 1 22.6 22.6 22.6
Dextrin MF30 19.4
Dextrin NDS
granulator GPCG-3 Procell 5 Procell 5 Procell 5 40
Table 5
Example Example Example Example Example Example 19 20 21 22 23 24
Clothianidin 48.0 48.0 48.0 48.0 48.0 48.0 NEWKALGEN WG-2 777 570 777 770 ~ 5.0 777 NEWKALGEN WG-4 777 777 777 777 777 770 sodium hydrogen 5.0 5.0 5.0 5.0 5.0 5.0 carbonate urea 7.0 7.0 3.0
Arabiccol SS 8.5 8.5 8.5 butyl parabene 0.1 0.1 0.1 0.1 0.1 0.1 anti foam e-20 0.5 077 777 777 777 777
Cyanine Green 0.3 0.3 0.3 0.3 0.3 0.3
Glucidex 1 22.6 29.6 38.1 22.6 35.1 38.1 ~~ granulator Procell Procell Procell Procell Procell Procell 5 5 5 5 5 5
Table 6
Compara- Compara- Compara- Compara- Comparative tive tive tive tive
Example 1 Example 2 Example 3 Example 4 Example 5 Clothianidin 48.0 48.0 48.0 ~~~ 48.0 48.0 newkalgen wG-2 777 777 " 777 777 777 newkalgen wG-4 777 777 777 777 777
Geropon SC-213 sodium hydrogen 5.0 5.0 5.0 5.0 carbonate urea 777 777 32.9 37.9 16.2 potassium dihydrogen 26.7 phosphate
Arabiccol SS 8.5 5.0 butyl parabene 0.1 0.1 0.1 0.1 antifoam E-20 777 777 777 777
Cyanine Green 0.3 0.3 0.5 0.5 0.5
Glucidex 1 35.7
Dextrin NDS
Argirec B22 22.6 granulation fluidized extrusion GPCG-3 GPCG-3 GPCG-3 method bed 41
Table 7
Comparative Comparative Comparative Comparative Example 6 Example 7 Example 8 Example 9 Clothianidin 48.0 48.0 48.0 48.0
NEWKALGEN
2.0 5.0 5.0 WG-2
NEWKALGEN
3.0 3.0 3.0 3.0 WG-4
Geropon SC- 5.0 213 sodium hydrogen 5.0 5.0 5.0 carbonate
Urea 16.2 potassium dihydrogen 29.7 phosphate
Arabiccol SS 5.0 5.0 butyl 0.1 0.1 0.1 0.1 parabene ANTIFOAM E- ' 0.5 0.5 0.5 0.5 20
Cyanine 0.5 0.5
Green
Glucidex 1
Dextrin NDS 37.9 33.4 33.4
Argirec B22 granulation GPCG-3 GPCG-3 GPCG-3 GPCG-3 method
Table 8
Comparative Comparative Example 10 Example 11 Clothianidin 48.0 48.0 NEWKALGEN WG-2 570 NEWKALGEN WG-4 77Ö 770
Geropon SC-213 5.0
Borresperse NA 22.9 17.9
Reax85 sodium hydrogen 15.0 15.0 carbonate ammonium sulfate 42
Arabiccol SS 5.0 10.0 butyl parabene 0.1 0.1 ANTIFOAM E-20 ÖTI Ö71
Cyanine Green 0.5 0.5
Argirec B22 granulation method GPCG-3 GPCG-3
Test Example 1
Measurement of Disintegration in Water
Into a 250 ml stoppered measuring cylinder filled with hard 5 water having a water hardness of 3 degrees, 0.0625 g of a test water dispersible granule was added (4,000-fold dilution). The cylinder was inverted for 2 seconds/one time, and the inversion was repeated until the water dispersible granule was completely dissolved. The number of times the inversion was repeated was 10 counted (hereinafter, referred to as "the inversion number").
The inversion number of 5 or less was regarded as "excellent" disintegration. The inversion number of 6 to 10 was regarded as "good" disintegration. The inversion number of 11 to 15 was regarded as "ordinary" disintegration. The inversion number of 15 16 or more was regarded as "poor" disintegration. Results are shown in Table 9 to Table 14.
20 25 43
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> [" >OD > OÏ >2 >2 ^ -H -H -H -H ^ -H ^ rH 4->© 4->© 4->© 4-) m 4-1 m (OrH ID H (TÏ i-H CU” (0 m HQ. HO, h75 QJ me me me m& mg'
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-¾ OH OH OH 0r3 0,3 tU o u u uu uu H ________ 49
As can be seen from the results of Test Example 1, the water dispersible granule of the present invention quickly disintegrated when it was put in water, and thus it clearly had excellent performance. Therefore, it is found that the water 5 dispersible granule of the present invention is useful in the application scene of agrichemicals which requires such performance.
Industrial Applicability 10 The water dispersible granule of the present invention is useful as one form of an agrochemical preparation.
15 20 25 30 35 1036979
Claims (9)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2008139363 | 2008-05-28 | ||
| JP2008139363 | 2008-05-28 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| NL1036979A1 NL1036979A1 (en) | 2009-12-01 |
| NL1036979C2 true NL1036979C2 (en) | 2013-07-23 |
Family
ID=41508521
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NL1036979A NL1036979C2 (en) | 2008-05-28 | 2009-05-20 | Water dispersible granule. |
Country Status (5)
| Country | Link |
|---|---|
| JP (1) | JP5375336B2 (en) |
| FR (1) | FR2931619B1 (en) |
| GR (1) | GR1007302B (en) |
| IT (1) | IT1397427B1 (en) |
| NL (1) | NL1036979C2 (en) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2011051205A1 (en) * | 2009-10-27 | 2011-05-05 | Basf Se | Production of pesticide granulates in a spouted bed apparatus |
| JP2011201780A (en) * | 2010-03-01 | 2011-10-13 | Sumika Enviro-Science Co Ltd | Water-soluble insecticide granule |
| JPWO2015046383A1 (en) * | 2013-09-30 | 2017-03-09 | 富士フイルム株式会社 | Process for producing drug substance-containing nucleus, drug substance-containing nucleus, pharmaceutical composition, and orally disintegrating tablet |
| KR101917604B1 (en) * | 2014-02-24 | 2018-11-13 | 한온시스템 주식회사 | Cooling Module |
| CN107889827A (en) * | 2017-10-25 | 2018-04-10 | 江苏腾龙生物药业有限公司 | A kind of 50% clothianidin wettable powder |
| JP7584776B2 (en) * | 2018-03-30 | 2024-11-18 | フマキラー株式会社 | Herbicides |
| JP2023060387A (en) * | 2020-06-08 | 2023-04-28 | 住友化学株式会社 | Infectious disease vector control method |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP3069665B2 (en) * | 1990-03-15 | 2000-07-24 | 住友化学工業株式会社 | Agricultural granular wettable powder composition |
| TW276982B (en) * | 1993-08-11 | 1996-06-01 | Ishihara Sangyo Kaisha | |
| WO1998034483A1 (en) * | 1997-02-10 | 1998-08-13 | Takeda Chemical Industries, Ltd. | Wettable or water-soluble granular agrochemical composition |
| JP4236314B2 (en) * | 1997-11-17 | 2009-03-11 | 科研製薬株式会社 | Polyoxin granule wettable powder |
| US6620421B1 (en) * | 1999-10-05 | 2003-09-16 | Sumitomo Chemical Company, Limited | Water dispersible granules |
| JP4632509B2 (en) * | 2000-10-10 | 2011-02-16 | クミアイ化学工業株式会社 | Agro-horticultural wettable powder |
| JP4666756B2 (en) * | 2000-12-14 | 2011-04-06 | バイエルクロップサイエンス株式会社 | Granular wettable powder |
| JP4280022B2 (en) * | 2002-04-02 | 2009-06-17 | バイエルクロップサイエンス株式会社 | Granular wettable powder |
| JP2003313102A (en) * | 2002-04-22 | 2003-11-06 | Sankyo Agro Kk | Pesticide granular wettable powder |
| WO2004014136A1 (en) * | 2002-08-07 | 2004-02-19 | Nippon Soda Co., Ltd. | Agricultural chemical composition in granular form |
| JP2007308482A (en) * | 2006-04-18 | 2007-11-29 | Nissan Chem Ind Ltd | Method for applying agrochemical |
| JP5009916B2 (en) * | 2006-08-10 | 2012-08-29 | 日本曹達株式会社 | Agrochemical composition |
-
2009
- 2009-05-20 NL NL1036979A patent/NL1036979C2/en not_active IP Right Cessation
- 2009-05-22 GR GR20090100294A patent/GR1007302B/en not_active IP Right Cessation
- 2009-05-26 FR FR0953458A patent/FR2931619B1/en active Active
- 2009-05-27 IT ITTO2009A000404A patent/IT1397427B1/en active
- 2009-05-28 JP JP2009128660A patent/JP5375336B2/en active Active
Also Published As
| Publication number | Publication date |
|---|---|
| ITTO20090404A1 (en) | 2009-11-29 |
| GR1007302B (en) | 2011-06-07 |
| FR2931619B1 (en) | 2015-02-27 |
| JP2010006802A (en) | 2010-01-14 |
| GR20090100294A (en) | 2009-12-31 |
| FR2931619A1 (en) | 2009-12-04 |
| IT1397427B1 (en) | 2013-01-10 |
| JP5375336B2 (en) | 2013-12-25 |
| NL1036979A1 (en) | 2009-12-01 |
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