ZA200201468B - Microcapsules. - Google Patents
Microcapsules. Download PDFInfo
- Publication number
- ZA200201468B ZA200201468B ZA200201468A ZA200201468A ZA200201468B ZA 200201468 B ZA200201468 B ZA 200201468B ZA 200201468 A ZA200201468 A ZA 200201468A ZA 200201468 A ZA200201468 A ZA 200201468A ZA 200201468 B ZA200201468 B ZA 200201468B
- Authority
- ZA
- South Africa
- Prior art keywords
- microcapsules
- active ingredient
- microcapsule
- oil
- phase
- Prior art date
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- 239000003094 microcapsule Substances 0.000 title claims description 65
- 229920000642 polymer Polymers 0.000 claims description 21
- 239000012868 active agrochemical ingredient Substances 0.000 claims description 20
- 239000000178 monomer Substances 0.000 claims description 19
- 239000012071 phase Substances 0.000 claims description 18
- 239000007787 solid Substances 0.000 claims description 16
- 239000002270 dispersing agent Substances 0.000 claims description 14
- 108010010803 Gelatin Proteins 0.000 claims description 13
- 229920000159 gelatin Polymers 0.000 claims description 13
- 235000019322 gelatine Nutrition 0.000 claims description 13
- 235000011852 gelatine desserts Nutrition 0.000 claims description 13
- 239000012074 organic phase Substances 0.000 claims description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 13
- 229920002396 Polyurea Polymers 0.000 claims description 12
- 239000008346 aqueous phase Substances 0.000 claims description 12
- 239000008273 gelatin Substances 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 10
- 239000002775 capsule Substances 0.000 claims description 8
- 239000004814 polyurethane Substances 0.000 claims description 8
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 8
- 239000000654 additive Substances 0.000 claims description 7
- 229920002635 polyurethane Polymers 0.000 claims description 7
- 239000007788 liquid Substances 0.000 claims description 6
- 229920002554 vinyl polymer Polymers 0.000 claims description 6
- 239000000417 fungicide Substances 0.000 claims description 5
- 230000015572 biosynthetic process Effects 0.000 claims description 4
- 239000003054 catalyst Substances 0.000 claims description 4
- 239000004009 herbicide Substances 0.000 claims description 4
- 239000003999 initiator Substances 0.000 claims description 4
- 239000002917 insecticide Substances 0.000 claims description 4
- 238000003756 stirring Methods 0.000 claims description 4
- 239000004971 Cross linker Substances 0.000 claims description 3
- 230000000895 acaricidal effect Effects 0.000 claims description 3
- 239000000642 acaricide Substances 0.000 claims description 3
- 230000000844 anti-bacterial effect Effects 0.000 claims description 3
- 239000003899 bactericide agent Substances 0.000 claims description 3
- 239000003750 molluscacide Substances 0.000 claims description 3
- 230000002013 molluscicidal effect Effects 0.000 claims description 3
- 239000005645 nematicide Substances 0.000 claims description 3
- 235000015097 nutrients Nutrition 0.000 claims description 3
- 239000005648 plant growth regulator Substances 0.000 claims description 3
- 239000002861 polymer material Substances 0.000 claims description 3
- 239000005871 repellent Substances 0.000 claims description 3
- 230000002940 repellent Effects 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 230000000855 fungicidal effect Effects 0.000 claims 1
- 230000002363 herbicidal effect Effects 0.000 claims 1
- 239000000203 mixture Substances 0.000 description 43
- -1 for example Chemical class 0.000 description 42
- 239000006185 dispersion Substances 0.000 description 40
- 239000004480 active ingredient Substances 0.000 description 34
- 239000002245 particle Substances 0.000 description 34
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 18
- 239000003921 oil Substances 0.000 description 18
- 239000002480 mineral oil Substances 0.000 description 14
- 239000004372 Polyvinyl alcohol Substances 0.000 description 11
- 239000000463 material Substances 0.000 description 11
- 229920002451 polyvinyl alcohol Polymers 0.000 description 11
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 10
- 239000011324 bead Substances 0.000 description 10
- 239000011734 sodium Substances 0.000 description 10
- IMROMDMJAWUWLK-UHFFFAOYSA-N Ethenol Chemical compound OC=C IMROMDMJAWUWLK-UHFFFAOYSA-N 0.000 description 9
- 229920001732 Lignosulfonate Polymers 0.000 description 9
- 125000002877 alkyl aryl group Chemical group 0.000 description 9
- 239000002518 antifoaming agent Substances 0.000 description 9
- 239000007864 aqueous solution Substances 0.000 description 9
- 239000008367 deionised water Substances 0.000 description 9
- 229910021641 deionized water Inorganic materials 0.000 description 9
- 239000000839 emulsion Substances 0.000 description 9
- 235000010446 mineral oil Nutrition 0.000 description 9
- HMZGPNHSPWNGEP-UHFFFAOYSA-N octadecyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)C(C)=C HMZGPNHSPWNGEP-UHFFFAOYSA-N 0.000 description 9
- 229920000151 polyglycol Polymers 0.000 description 9
- 239000010695 polyglycol Substances 0.000 description 9
- 229920001296 polysiloxane Polymers 0.000 description 9
- 238000004062 sedimentation Methods 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 9
- 241000196324 Embryophyta Species 0.000 description 8
- 239000004952 Polyamide Substances 0.000 description 8
- 239000012948 isocyanate Substances 0.000 description 8
- 229920002647 polyamide Polymers 0.000 description 8
- 238000002360 preparation method Methods 0.000 description 7
- SAPGBCWOQLHKKZ-UHFFFAOYSA-N 6-(2-methylprop-2-enoyloxy)hexyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCCCCOC(=O)C(C)=C SAPGBCWOQLHKKZ-UHFFFAOYSA-N 0.000 description 6
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical class CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 6
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 6
- AVTLBBWTUPQRAY-UHFFFAOYSA-N 2-(2-cyanobutan-2-yldiazenyl)-2-methylbutanenitrile Chemical compound CCC(C)(C#N)N=NC(C)(CC)C#N AVTLBBWTUPQRAY-UHFFFAOYSA-N 0.000 description 5
- KQWGXHWJMSMDJJ-UHFFFAOYSA-N cyclohexyl isocyanate Chemical compound O=C=NC1CCCCC1 KQWGXHWJMSMDJJ-UHFFFAOYSA-N 0.000 description 5
- 150000002513 isocyanates Chemical class 0.000 description 5
- PXMNMQRDXWABCY-UHFFFAOYSA-N 1-(4-chlorophenyl)-4,4-dimethyl-3-(1H-1,2,4-triazol-1-ylmethyl)pentan-3-ol Chemical compound C1=NC=NN1CC(O)(C(C)(C)C)CCC1=CC=C(Cl)C=C1 PXMNMQRDXWABCY-UHFFFAOYSA-N 0.000 description 4
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 4
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 4
- 239000005839 Tebuconazole Substances 0.000 description 4
- 235000013877 carbamide Nutrition 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 229920001577 copolymer Polymers 0.000 description 4
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
- 229920000768 polyamine Polymers 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 229920002818 (Hydroxyethyl)methacrylate Polymers 0.000 description 3
- HOKKPVIRMVDYPB-UVTDQMKNSA-N (Z)-thiacloprid Chemical compound C1=NC(Cl)=CC=C1CN1C(=N/C#N)/SCC1 HOKKPVIRMVDYPB-UVTDQMKNSA-N 0.000 description 3
- OSSNTDFYBPYIEC-UHFFFAOYSA-N 1-ethenylimidazole Chemical compound C=CN1C=CN=C1 OSSNTDFYBPYIEC-UHFFFAOYSA-N 0.000 description 3
- YOYAIZYFCNQIRF-UHFFFAOYSA-N 2,6-dichlorobenzonitrile Chemical compound ClC1=CC=CC(Cl)=C1C#N YOYAIZYFCNQIRF-UHFFFAOYSA-N 0.000 description 3
- OLQFXOWPTQTLDP-UHFFFAOYSA-N 2-(2-hydroxyethoxy)ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOCCO OLQFXOWPTQTLDP-UHFFFAOYSA-N 0.000 description 3
- RWXMAAYKJDQVTF-UHFFFAOYSA-N 2-(2-hydroxyethoxy)ethyl prop-2-enoate Chemical compound OCCOCCOC(=O)C=C RWXMAAYKJDQVTF-UHFFFAOYSA-N 0.000 description 3
- JKNCOURZONDCGV-UHFFFAOYSA-N 2-(dimethylamino)ethyl 2-methylprop-2-enoate Chemical compound CN(C)CCOC(=O)C(C)=C JKNCOURZONDCGV-UHFFFAOYSA-N 0.000 description 3
- MZGMQAMKOBOIDR-UHFFFAOYSA-N 2-[2-(2-hydroxyethoxy)ethoxy]ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOCCOCCO MZGMQAMKOBOIDR-UHFFFAOYSA-N 0.000 description 3
- VETIYACESIPJSO-UHFFFAOYSA-N 2-[2-(2-hydroxyethoxy)ethoxy]ethyl prop-2-enoate Chemical compound OCCOCCOCCOC(=O)C=C VETIYACESIPJSO-UHFFFAOYSA-N 0.000 description 3
- QLIBJPGWWSHWBF-UHFFFAOYSA-N 2-aminoethyl methacrylate Chemical compound CC(=C)C(=O)OCCN QLIBJPGWWSHWBF-UHFFFAOYSA-N 0.000 description 3
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 239000005940 Thiacloprid Substances 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- NNVDGGDSRRQJMV-UHFFFAOYSA-L [dioctyl(2,2,5,5-tetramethylhexanoyloxy)stannyl] 2,2,5,5-tetramethylhexanoate Chemical compound CCCCCCCC[Sn](OC(=O)C(C)(C)CCC(C)(C)C)(OC(=O)C(C)(C)CCC(C)(C)C)CCCCCCCC NNVDGGDSRRQJMV-UHFFFAOYSA-L 0.000 description 3
- 229920006318 anionic polymer Polymers 0.000 description 3
- 239000004202 carbamide Substances 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 239000003086 colorant Substances 0.000 description 3
- 239000010949 copper Substances 0.000 description 3
- 229910052802 copper Inorganic materials 0.000 description 3
- 150000004985 diamines Chemical class 0.000 description 3
- KORSJDCBLAPZEQ-UHFFFAOYSA-N dicyclohexylmethane-4,4'-diisocyanate Chemical compound C1CC(N=C=O)CCC1CC1CCC(N=C=O)CC1 KORSJDCBLAPZEQ-UHFFFAOYSA-N 0.000 description 3
- 235000014113 dietary fatty acids Nutrition 0.000 description 3
- 150000002009 diols Chemical class 0.000 description 3
- GMSCBRSQMRDRCD-UHFFFAOYSA-N dodecyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCCCOC(=O)C(C)=C GMSCBRSQMRDRCD-UHFFFAOYSA-N 0.000 description 3
- 239000000194 fatty acid Substances 0.000 description 3
- 229930195729 fatty acid Natural products 0.000 description 3
- NYPJDWWKZLNGGM-UHFFFAOYSA-N fenvalerate Aalpha Natural products C=1C=C(Cl)C=CC=1C(C(C)C)C(=O)OC(C#N)C(C=1)=CC=CC=1OC1=CC=CC=C1 NYPJDWWKZLNGGM-UHFFFAOYSA-N 0.000 description 3
- 229920005862 polyol Polymers 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- 229920001567 vinyl ester resin Chemical group 0.000 description 3
- PILKNUBLAZTESB-UHFFFAOYSA-N (4-tert-butylcyclohexyl) 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC1CCC(C(C)(C)C)CC1 PILKNUBLAZTESB-UHFFFAOYSA-N 0.000 description 2
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
- GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical compound CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- MCWMYICYUGCRDY-UHFFFAOYSA-N 2-[2-[2-(2-hydroxyethoxy)ethoxy]ethoxy]ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOCCOCCOCCO MCWMYICYUGCRDY-UHFFFAOYSA-N 0.000 description 2
- QUASZQPLPKGIJY-UHFFFAOYSA-N 2-[2-[2-(2-hydroxyethoxy)ethoxy]ethoxy]ethyl prop-2-enoate Chemical compound OCCOCCOCCOCCOC(=O)C=C QUASZQPLPKGIJY-UHFFFAOYSA-N 0.000 description 2
- DJKKWVGWYCKUFC-UHFFFAOYSA-N 2-butoxyethyl 2-methylprop-2-enoate Chemical compound CCCCOCCOC(=O)C(C)=C DJKKWVGWYCKUFC-UHFFFAOYSA-N 0.000 description 2
- PTJDGKYFJYEAOK-UHFFFAOYSA-N 2-butoxyethyl prop-2-enoate Chemical compound CCCCOCCOC(=O)C=C PTJDGKYFJYEAOK-UHFFFAOYSA-N 0.000 description 2
- RCEJCSULJQNRQQ-UHFFFAOYSA-N 2-methylbutanenitrile Chemical compound CCC(C)C#N RCEJCSULJQNRQQ-UHFFFAOYSA-N 0.000 description 2
- RUMACXVDVNRZJZ-UHFFFAOYSA-N 2-methylpropyl 2-methylprop-2-enoate Chemical compound CC(C)COC(=O)C(C)=C RUMACXVDVNRZJZ-UHFFFAOYSA-N 0.000 description 2
- CFVWNXQPGQOHRJ-UHFFFAOYSA-N 2-methylpropyl prop-2-enoate Chemical compound CC(C)COC(=O)C=C CFVWNXQPGQOHRJ-UHFFFAOYSA-N 0.000 description 2
- ILZXXGLGJZQLTR-UHFFFAOYSA-N 2-phenylethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCC1=CC=CC=C1 ILZXXGLGJZQLTR-UHFFFAOYSA-N 0.000 description 2
- HPSGLFKWHYAKSF-UHFFFAOYSA-N 2-phenylethyl prop-2-enoate Chemical compound C=CC(=O)OCCC1=CC=CC=C1 HPSGLFKWHYAKSF-UHFFFAOYSA-N 0.000 description 2
- KUDUQBURMYMBIJ-UHFFFAOYSA-N 2-prop-2-enoyloxyethyl prop-2-enoate Chemical compound C=CC(=O)OCCOC(=O)C=C KUDUQBURMYMBIJ-UHFFFAOYSA-N 0.000 description 2
- NWKKCUWIMOZYOO-UHFFFAOYSA-N 3-methoxybutyl 2-methylprop-2-enoate Chemical compound COC(C)CCOC(=O)C(C)=C NWKKCUWIMOZYOO-UHFFFAOYSA-N 0.000 description 2
- NPYMXLXNEYZTMQ-UHFFFAOYSA-N 3-methoxybutyl prop-2-enoate Chemical compound COC(C)CCOC(=O)C=C NPYMXLXNEYZTMQ-UHFFFAOYSA-N 0.000 description 2
- RXXZODOCQIRRQA-UHFFFAOYSA-N 3-phenylpropyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCC1=CC=CC=C1 RXXZODOCQIRRQA-UHFFFAOYSA-N 0.000 description 2
- PKBZUGSITIBLFK-UHFFFAOYSA-N 3-phenylpropyl prop-2-enoate Chemical compound C=CC(=O)OCCCC1=CC=CC=C1 PKBZUGSITIBLFK-UHFFFAOYSA-N 0.000 description 2
- BQMRHYBXRAYYQS-UHFFFAOYSA-N 4-dihydroxyphosphinothioyloxy-n,n-diethyl-6-methylpyrimidin-2-amine Chemical compound CCN(CC)C1=NC(C)=CC(OP(O)(O)=S)=N1 BQMRHYBXRAYYQS-UHFFFAOYSA-N 0.000 description 2
- JTHZUSWLNCPZLX-UHFFFAOYSA-N 6-fluoro-3-methyl-2h-indazole Chemical compound FC1=CC=C2C(C)=NNC2=C1 JTHZUSWLNCPZLX-UHFFFAOYSA-N 0.000 description 2
- NCJMGBLMNBSQOT-UHFFFAOYSA-N 9-phenylnonyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCCCCCCCC1=CC=CC=C1 NCJMGBLMNBSQOT-UHFFFAOYSA-N 0.000 description 2
- GZIXJUKKQFBAJP-UHFFFAOYSA-N 9-phenylnonyl prop-2-enoate Chemical compound C=CC(=O)OCCCCCCCCCC1=CC=CC=C1 GZIXJUKKQFBAJP-UHFFFAOYSA-N 0.000 description 2
- 239000005660 Abamectin Substances 0.000 description 2
- 244000215068 Acacia senegal Species 0.000 description 2
- MDNWOSOZYLHTCG-UHFFFAOYSA-N Dichlorophen Chemical compound OC1=CC=C(Cl)C=C1CC1=CC(Cl)=CC=C1O MDNWOSOZYLHTCG-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- 239000005562 Glyphosate Substances 0.000 description 2
- 229920000084 Gum arabic Polymers 0.000 description 2
- 239000005906 Imidacloprid Substances 0.000 description 2
- 229920000877 Melamine resin Polymers 0.000 description 2
- 239000005956 Metaldehyde Substances 0.000 description 2
- 239000005951 Methiocarb Substances 0.000 description 2
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
- 239000004721 Polyphenylene oxide Substances 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- LCXXNKZQVOXMEH-UHFFFAOYSA-N Tetrahydrofurfuryl methacrylate Chemical compound CC(=C)C(=O)OCC1CCCO1 LCXXNKZQVOXMEH-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 239000000205 acacia gum Substances 0.000 description 2
- 235000010489 acacia gum Nutrition 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-M acrylate group Chemical group C(C=C)(=O)[O-] NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- FPIPGXGPPPQFEQ-OVSJKPMPSA-N all-trans-retinol Chemical compound OC\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-OVSJKPMPSA-N 0.000 description 2
- ZOJBYZNEUISWFT-UHFFFAOYSA-N allyl isothiocyanate Chemical compound C=CCN=C=S ZOJBYZNEUISWFT-UHFFFAOYSA-N 0.000 description 2
- 150000003863 ammonium salts Chemical class 0.000 description 2
- 239000007798 antifreeze agent Substances 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- 235000006708 antioxidants Nutrition 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- CJJOSEISRRTUQB-UHFFFAOYSA-N azinphos-methyl Chemical compound C1=CC=C2C(=O)N(CSP(=S)(OC)OC)N=NC2=C1 CJJOSEISRRTUQB-UHFFFAOYSA-N 0.000 description 2
- AOJOEFVRHOZDFN-UHFFFAOYSA-N benzyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC1=CC=CC=C1 AOJOEFVRHOZDFN-UHFFFAOYSA-N 0.000 description 2
- GCTPMLUUWLLESL-UHFFFAOYSA-N benzyl prop-2-enoate Chemical compound C=CC(=O)OCC1=CC=CC=C1 GCTPMLUUWLLESL-UHFFFAOYSA-N 0.000 description 2
- LLEMOWNGBBNAJR-UHFFFAOYSA-N biphenyl-2-ol Chemical compound OC1=CC=CC=C1C1=CC=CC=C1 LLEMOWNGBBNAJR-UHFFFAOYSA-N 0.000 description 2
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 2
- KXRPCFINVWWFHQ-UHFFFAOYSA-N cadusafos Chemical compound CCC(C)SP(=O)(OCC)SC(C)CC KXRPCFINVWWFHQ-UHFFFAOYSA-N 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 2
- 229920002678 cellulose Polymers 0.000 description 2
- FCSHDIVRCWTZOX-DVTGEIKXSA-N clobetasol Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@H](C)[C@@](C(=O)CCl)(O)[C@@]1(C)C[C@@H]2O FCSHDIVRCWTZOX-DVTGEIKXSA-N 0.000 description 2
- 229910000365 copper sulfate Inorganic materials 0.000 description 2
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 2
- MZZBPDKVEFVLFF-UHFFFAOYSA-N cyanazine Chemical compound CCNC1=NC(Cl)=NC(NC(C)(C)C#N)=N1 MZZBPDKVEFVLFF-UHFFFAOYSA-N 0.000 description 2
- OIWOHHBRDFKZNC-UHFFFAOYSA-N cyclohexyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC1CCCCC1 OIWOHHBRDFKZNC-UHFFFAOYSA-N 0.000 description 2
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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
- A01N25/26—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 in coated particulate form
- A01N25/28—Microcapsules or nanocapsules
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- 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
- A01N25/02—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing liquids as carriers, diluents or solvents
- A01N25/04—Dispersions, emulsions, suspoemulsions, suspension concentrates or gels
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
- A01N25/08—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing solids as carriers or diluents
- A01N25/10—Macromolecular compounds
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/34—Nitriles
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- 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
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
- A01N43/647—Triazoles; Hydrogenated triazoles
- A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
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- 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
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
- A01N43/78—1,3-Thiazoles; Hydrogenated 1,3-thiazoles
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- 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
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
- A01N47/36—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the group >N—CO—N< directly attached to at least one heterocyclic ring; Thio analogues thereof
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- 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
- A01N51/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds having the sequences of atoms O—N—S, X—O—S, N—N—S, O—N—N or O-halogen, regardless of the number of bonds each atom has and with no atom of these sequences forming part of a heterocyclic ring
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- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Health & Medical Sciences (AREA)
- Dentistry (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Engineering & Computer Science (AREA)
- Agronomy & Crop Science (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Toxicology (AREA)
- Chemical & Material Sciences (AREA)
- Dispersion Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Manufacturing Of Micro-Capsules (AREA)
Description
; v -1- 4 id
Microcapsules
The present invention relates to novel microcapsules comprising agrochemical active ingredients, to a process for preparing these microcapsules and to their use for applying agrochemical active ingredients. :
Microencapsulation is a method which has been used for a long time to convert, for example, dyes, inks, flavors, pharmaceutically active ingredients or agrochemicals into preparations from which the encapsulated components are released under controlled conditions. .
Thus, WO 95/13698 discloses microcapsules comprising a solid biologically active ingredient dispersed in a liquid.
WO 92/10285 describes microcapsules which comprise agrochemical active ingredients such as herbicides, insecticides or fungicides or else fertilizers and have a temperature-dependent permeability profile. Furthermore, WO 91/12884 discloses the preparation of thermo- and/or photosensitive microcapsules.
Moreover, EP-A 0 270 742 relates to microcapsules whose ingredients are fungicides and whose capsule walls consist of polyamide or polyurethane.
GB-A 2 011 341 concerns a special process for microencapsulation by phase interface condensation where a reactive amine component is released from a salt.
US-A 4 285 720 discloses a process for microencapsulating water-imiscible material where the capsule wall is formed as a polyurea envelope from an isocyanate monomer and water, without addition of a further reactive component.
x . = ve
Finally, JP-A 1998-059 811 and JP-A 1998-182 319 relate to microcapsules having an envelope of polyurea and a core of polyurethane gel which comprises allyl isothiocyanate as liquid active ingredient.
The microcapsules described above have the disadvantage that they have relatively low mechanical stability, which, in many applications, is undesirable. Thus, in the case of microcapsules comprising agrochemical active ingredients, which are generally used as aqueous dispersions, mechanical stresses encountered during pumping, transporting, stirring or spraying, may result in the envelope being damaged, with an associated undesirable premature release of the active ingredients. : A further disadvantage of the known microcapsules is the fact that the envelopes are damaged or even ruptured when the capsule dispersion, after outdoor application, dries up or is subjected to cycles of drying up and rehumidification, owing to the weather.
The present invention now provides microcapsules consisting of
D an envelope produced from a polymer material and
I) an envelope content of al) a continuous solid polymer phase, a2) a liquid oil phase, a3) at least one agrochemical active ingredient, a4) at least one oil-soluble dispersant and as) optionally additives, where the content of the agrochemical active ingredient, based on the overall weight of the capsules, ranges between 1 and 75% by weight. :
Furthermore, it has been found that microcapsules according to the invention are obtained when b ‘e AK J
A) an organic phase of a0) monomers capable of forming a continuous solid polymer phase, a2) aliquid oil phase, a3) atleast one agrochemical active ingredient, a4) atleast one oil-soluble dispersant and al) optionally additives, a6) optionally initiators and catalysts and a7) optionally at least one oil-soluble wall-forming component
B) in an aqueous phase of bl) water, b2) at least one water-soluble dispersant and b3) atleast one water-soluble wall-forming component is, with stirring at temperatures between 0°C and 80°C, dispersed into fine droplets, ©) then allowed to react with formation of microcapsules and
D) then allowed to cure at elevated temperature.
Finally, it has been found that the microcapsules according to the invention are highly suitable for applying agrochemical active ingredients, in particular for spray application and for seed dressing.
It is extremely surprising that the microcapsules according to the invention are more suitable for applying agrochemical active ingredients, in particular solid active ingredients, than the prior-art preparations of the most similar constitution. It is
I v . " particularly unexpected that the microcapsules according to the invention, in spite of the fact that they have thin capsule walls, have a considerably higher mechanical stability than similar prior-art formulations of this type.
The microcapsules according to the invention have a number of advantages. Thus, they are capable of releasing the active components over a relatively long period of time at a uniform rate. Finally, it is also particularly advantageous that the microcapsules according to the invention are substantially stable when subjected to the mechanical stress encountered in practice.
Preferred polymer material for the envelope (I) of the microcapsules according to the invention are polyurethanes, polyureas, polyamides, melamine-formaldehyde condensates, phenol-formaldehyde-urea condensates and gelatin including hardened gelatin and gelatin complex coacervates, for example complex coacervates of gelatin and gum arabic. Particular preference is given to envelopes of polyurea.
Such polyurea envelopes can preferably be produced by phase interface polyaddition - of diisocyanates and/or polyisocyanates and diamines and/or polyamines.
The solid polymer phase (al) present in the microcapsules according to the invention can belong to different classes of polymers. Thus, the polymer may consist, for example, of polymerized units of vinyl monomers and crosslinkers.
For the purpose of the invention, vinyl monomers are primarily aromatic vinyl compounds such as styrene, o-methyl styrene, ethylvinylbenzene, vinylnaphthalene and (meth)acrylic acid esters, such as, for example, methyl methacrylate, ethyl acrylate and hydroxyethyl methacrylate, benzyl acrylate, benzyl methacrylate, phenylethyl acrylate, phenylethyl methacrylate, phenylpropyl acrylate, phenylpropyl methacrylate, phenylnonyl acrylate, phenylnonyl methacrylate, 3-methoxybutyl acrylate, 3-methoxybutyl methacrylate, butoxyethyl acrylate, butoxyethyl methacrylate, diethylene glycol monoacrylate, diethylene glycol monomethacrylate,
i . w triethylene glycol monoacrylate, triethylene glycol monomethacrylate, tetraethylene glycol monoacrylate, tetracthylene glycol monomethacrylate, furfuryl acrylate, furfuryl methacrylate, tetrahydrofurfuryl acrylate and tetrahydrofurfuryl methacrylate.
Further suitable vinyl monomers are acrylonitrile, vinyl chloride, vinylidene chloride, vinyl acetate and vinyl propionate.
Preference is given to vinyl monomers having Cs-Cj;-alkyl radicals, such as n-butyl acrylate, n-butyl methacrylate, isobutyl acrylate, isobutyl methacrylate, n-hexyl acrylate, n-hexyl methacrylate, ethylhexyl acrylate, ethylhexyl methacrylate, n-octyl acrylate, n-octyl methacrylate, decyl acrylate, decyl methacrylate, dodecyl acrylate, dodecyl methacrylate, stearyl acrylate, stearyl methacrylate, cyclohexyl acrylate, cyclohexyl methacrylate, 4-tert-butylcyclohexyl methacrylate, vinyl laurate, vinyl stearate and vinyl adipate.
Preference is also given to mixtures of different vinyl monomers.
Examples of particularly preferred (meth)acrylic acid esters which may be mentioned are: n-butyl acrylate, n-butyl methacrylate, isobutyl acrylate, isobutyl methacrylate, n- hexyl acrylate, n-hexyl methacrylate, ethylhexyl acrylate, ethylhexyl methacrylate, n- octyl acrylate, n-octyl methacrylate, decyl acrylate, decyl methacrylate, dodecyl acrylate, dodecyl methacrylate, stearyl acrylate, stearyl methacrylate, cyclohexyl acrylate, cyclohexyl methacrylate, 4-tert-butylcyclohexyl methacrylate, benzyl acrylate, benzyl methacrylate, phenylethyl acrylate, phenylethyl methacrylate, phenylpropyl acrylate, phenylpropyl methacrylate, phenylnonyl acrylate, phenylnonyl methacrylate, 3-methoxybutyl acrylate, 3-methoxybutyl methacrylate, butoxyethyl acrylate, butoxyethyl methacrylate, diethylene glycol monoacrylate, diethylene glycol monomethacrylate, triethylene glycol monoacrylate, triethylene glycol monomethacrylate, tetracthylene glycol monoacrylate, tetraethylene glycol monomethacrylate, furfuryl acrylate, furfuryl methacrylate, tetrahydrofurfuryl acrylate and tetrahydrofurfuryl methacrylate.
bd kd
Crosslinkers which may be mentioned by way of example are allyl methacrylate, ethylene glycol dimethacrylate, ethylene glycol diacrylate, butanediol diacrylate, butanediol dimethacrylate, neopentyl glycol dimethacrylate, hexanediol dimethacrylate, triethylene glycol dimethacrylate, tetraethylene glycol dimethacrylate, trimethylolpropane triacrylate, pentaerythritol tetramethacrylate and divinylbenzene.
The continuous solid polymer phase (al) may also consist of polyurethane or polyurea. Preference is given to polyurethanes. Suitable polyurethanes can be prepared from aliphatic and/or aromatic isocyanates and di- or polyols. In the present context, isocyanates are to be understood as meaning difunctional and multifunctional aromatic and aliphatic isocyanates. Examples which may be mentioned are: m-phenylene diisocyanate, p-phenylene diisocyanate, toluene 2.4- diisocyanate, 3,3’-dimethyl-4,4"-biphenylene diisocyanate, 4,4 "-methylenebis(2- methylphenyl isocyanate), hexamethylene diisocyanate; 4.4 - methylenebis(cyclohexyl diisocyanate). The diols used can be polyesters and polyether diols. Preference is given to polyether diols based on polyethylene oxide, polyethylene oxide/polypropylene oxide and tetrahydrofuran. To obtain crosslinking, it is also possible to use proportionate amounts of polyol compounds, such as ethylene-oxide-extended trimethylolpropane or castor oil.
Further suitable polymers (al) are polyesters, polyamides and condensates of + phenols, urea and formaldehyde.
Suitable for the liquid oil phase (a2) are vegetable and animal oils, synthetic oils and mineral oils. Preference is given to mineral oils. Both mineral oils which have been purified by distillation and oils which have not been distilled, i.e. residue oils, are suitable. Preference is given to mineral oils having a boiling point of from 75 to 370°C, in particular from 100 to 370°C. In many cases, mineral oils having a high proportion of paraffin and isoparaffin are highly suitable.
v 4 "7
In the present context, agrochemical active ingredients (a3) are to be understood as : - meaning all substances customarily used for treating plants. By preference, fungicides, bactericides, insecticides, acaricides, nematicides, molluscicides, herbicides, plant growth regulators, plant nutrients and repellents may be mentioned.
Preference is given to solid agrochemical active ingredients.
Examples of fungicides which may be mentioned are: 2-anilino-4-methyl-6-cyclopropylpyrimidine; 2°,6’-dibromo-2-methyl-4*- trifluoromethoxy-4*-trifluoromethyl-1,3-thiazole-5-carboxanilide; 2,6-dichloro-N-(4- trifluoromethylbenzyl)benzamide; (E)-2-methoximino-N-methyl-2-(2- phenoxyphenyl)acetamide; 8-hydroxyquinoline sulfate; methyl (E)-2-{2-[6-(2-cyanophenoxy)pyrimidine-4-yloxy]phenyl}-3-methoxy acrylate; methyl (E)-methoximino[alpha-(o-tolyloxy)-o-tolyl]acetate; 2-phenylphenol (OPP), aldimorph, ampropylfos, anilazin, azaconazole, benalaxyl, benodanil, benomyl, binapacryl, biphenyl, bitertanol, blasticidin-S, bromuconazole, bupirimate, buthiobate, calcium polysulfide, captafol, captan, carbendazim, carboxin, quinomethionate chloroneb, chloropicrin, chlorothalonil, chlozolinate, cufraneb, cymoxanil, cyproconazole, cyprofuram, dichlorophene, diclobutrazole, dichlofluanide, diclomezin, dicloran, diethofencarb, difenoconazole, dimethirimol, dimethomorph, diniconazole, dinocap, diphenylamine, dipyrithion, ditalimfos, dithianon, dodine, drazoxolon, edifenphos, epoxyconazole, ethirimol, etridiazole, fenarimol, fenbuconazole, fenfuram, fenitropan, fenpiclonil, fenpropidin, fenpropimorph, fentin acetate, fentin hydroxide, ferbam, ferimzone, fluazinam, fludioxonil, fluoromide, fluquinconazole, flusilazole, flusulfamide, flutolanil, flutriafol, folpet, fosetyl-aluminum, fthalide, fuberidazole, furalaxyl, furmecyclox, guazatine, hexachlorobenzene, hexaconazole, hymexazol, imazalil, imibenconazole, iminoctadin, iprobenfos (IBP), iprodion, isoprothiolan,
¥ kd kasugamycin, copper preparations such as: copper hydroxide, copper naphtenate, copper oxychloride, copper sulfate, copper oxide, oxine-copper and Bordeaux mixture, mancopper, mancozeb, maneb, mepanipyrim, mepronil, metalaxyl, metconazole, methasulfocarb, methfuroxam, metiram, metsulfovax, myclobutanil, nickel dimethyldithiocarbamate, nitrothalisopropyl, nuarimol, ofurace, oxadixyl, oxamocarb, oxycarboxin, pefurazoate, penconazole, pencycuron, phosdiphen, pimaricin, piperalin, polyoxin, probenazole, prochloraz, procymidone, propamocarb, propiconazole, propineb, : 10 pyrazophos, pyrifenox, pyrimethanil, pyroquilon, quintozene (PCNB), quinoxyfen, sulfur and sulfur preparations, tebuconazole, tecloftalam, tecnazen, tetraconazole, thiabendazole, thicyofen, thiophanate-methyl, thiram, tolclophos-methyl, tolylfluanid, triadimefon, triadimenol, triazoxide, trichlamid, tricyclazole, tridemorph, triflumizole, triforine, triticonazole, validamycin A, vinclozolin,
Zineb, Ziram, 8-tert-butyl-2-(N-ethyl-N-n-propyl-amino)-methyl-1,4-dioxa-spiro-[4,5]decane,
N-(R)-[1-(4-chlorophenyl)-ethyl]-2,2-dichloro-1-ethyl-3t-methyl-1r- cyclopropanecarboxamide (diastereomer mixture or individual isomers), 1-methylethyl ~~ [2-methyl-1-[[[1-(4-methylphenyl)-ethyl]-amino]-carbonyl]-propyl]- carbamate, (2,3-dichloro-4-hydroxy)-1-methyl-cyclohexyl-1-carboxanilide, 2-[2-(1-chloro-cyclopropyl)-3-(2-chlorophenyl)-2-hydroxypropyl}-2,4-dihydro- [1,2,4]-triazole-3-thione and 1-(3,5-dimethyl-isoxazole-4-sulfonyl)-2-chloro-6,6-difluoro-[1,3]-dioxolo-[4,5-f]- benzimidazole.
Examples of bactericides which may be mentioned are:
' » bronopol, dichlorophen, nitrapyrin, nickel dimethyldithiocarbamate, kasugamycin, octhilinone, furane carboxylic acid, oxytetracyclin, probenazole, streptomycin, tecloftalam, copper sulfate and other copper preparations.
Examples of insecticides, acaricides and nematicides which may be mentioned are; abamectin, acephate, acrinathrin, alanycarb, aldicarb, alphamethrin, amitaz, avermectin, AZ 60541, azadirachtin, azinphos A, azinphos M, azocyclotin,
Bacillus thuringiensis, 4-bromo-2-(4-chlorophenyl)- 1-(ethoxymethyl)- 5-(trifluoromethyl)-1H-pyrrole-3-carbonitrile, bendiocarb, benfuracarb, bensulap, betacyfluthrin, bifenthrin, BPMC, brofenprox, bromophos A, bufencarb, buprofezin, butocarboxin, butylpyridaben, cadusafos, carbaryl, carbofuran, carbophenothion, carbosulfan, cartap, chloethocarb, chloretoxyfos, chlorfenvinphos, chlorfluazuron, chlormephos, N-[(6-chloro-3- pyridinyl)-methyl]-N-cyano-N-methyl-ethanimidamide, chlorpyrifos, chlorpyrifos M, cis-resmethrin, clocythrin, clofentezine, cyanophos, cycloprothrin, cyfluthrin, cyhalothrin, cyhexatin, cypermethrin, cyromazine, deltamethrin, demeton-M, demeton-S, demeton-S-methyl, diafenthiuron, diazinon, dichlofenthion, dichlorvos, dicliphos, dicrotophos, diethion, diflubenzuron, dimethoate, dimethylvinphos, dioxathion, disulfoton, emamectin, esfenvalerate, ethiofencarb, ethion, ethofenprox, ethoprophos, etrimphos, fenamiphos, fenazaquin, fenbutatin oxide, fenitrothion, fenobucarb, fenothiocarb, fenoxycarb, fenpropathrin, fenpyrad, fenpyroximate, fenthion, fenvalerate, fipronil, fluazuron, flucycloxuron, flucythrinate, flufenoxuron, flufenprox, fluvalinate, fonophos, formothion, fosthiazate, fubfenprox, furathiocarb,
HCH, heptenophos, hexaflumuron, hexythiazox, imidacloprid, isazophos, isofenphos, isoprocarb, isoxathion, ivermectin, lambda- cyhalothrin, lufenuron, malathion, mecarbam, mevinphos, mesulfenphos, metaldehyde, methacrifos, methamidophos, methidathion, methiocarb, methomyl, metolcarb, milbemeciin, monocrotophos, moxidectin,
. » naled, NC 184, nitenpyram, omethoat, oxamyl, oxydemethon M, oxydeprofos, parathion A, parathion M, permethrin, phenthoate, phorate, phosalone, phosmet, phosphamidon, phoxim, pirimicarb, pirimiphos M, pirimiphos A, profenophos, promecarb, propaphos, propoxur, prothiophos, prothoate, pymetrozin, pyrachlophos, pyridaphenthion, pyresmethrin, pyrethrum, pyridaben, pyrimidifen, pyriproxifen, quinalphos, salithion, sebufos, silafluofen, sulfotep, sulprofos, tebufenozide, tebufenpyrad, tebupirimiphos, teflubenzuron, tefluthrin, temephos, terbam, terbufos, tetrachlorvinphos, thiacloprid, thiafenox, thiamethoxam, thiodicarb, thiofanox, thiomethon, thionazin, thuringiensin, tralomethrin, transfluthrin, triarathene, triazophos, triazuron, trichlorfon, triflumuron, trimethacarb, vamidothion, XMC, xylylcarb, zetamethrin.
Examples of molluscicides which may be mentioned are metaldehyde and methiocarb.
Examples of herbicides which may be mentioned are: anilides such as, for example, diflufenican and propanil; aryl carboxylic acids such as, for example, dichloropicolinic acid, dicamba and picloram; aryloxyalkanoic acids such as, for example, 2,4-D, 2,4-DB, 2.4-DP, fluroxypyr, MCPA, MCPP and triclopyr; aryloxy-phenoxy-alkanoates such as, for example, diclofop-methyl, fenoxaprop-ethyl, fluazifop-butyl, haloxyfop-methyl and quizalofop-ethyl; azinones such as, for example, chloridazon and norflurazon; carbamates such as, for example, chlorpropham, desmedipham, phenmedipham and propham; chloroacetanilides such : as, for example, alachlor, acetochlor, butachlor, metazachlor, metolachlor, pretilachlor and propachlor; dinitroanilines such as, for example, oryzalin, pendimethalin and trifluralin; - diphenyl ethers such as, for example, acifluorfen, bifenox, fluoroglycofen, fomesafen, halosafen, lactofen and oxyfluorfen; ureas such as, for example, chlortoluron, diuron, fluometuron, isoproturon, linuron and methabenzthiazuron; hydroxylamines such as, for example, alloxydim, clethodim,
. » cycloxydim, sethoxydim and tralkoxydim; imidazolinones such as, for example, imazethapyr, imazamethabenz, imazapyr and imazaquin; nitriles such as, for example, bromoxynil, dichlobenil and ioxynil; oxyacetamides such as, for example, mefenacet; sulfonylureas such as, for example, amidosulfuron, bensulfuron-metyl, chlorimuron-ethyl, chlorsulfuron, cinosulfuron, metsulfuron-methyl, nicosulfuron, primisulfuron, pyrazosulfuron-ethyl, thifensulfuron-methyl, triasulfuron and tribenuron-methyl; thiolcarbamates such as, for example, butylate, cycloate, diallate,
EPTC, esprocarb, molinate, prosulfocarb, thiobencarb and tri-allate; triazines such as, for example, atrazine, cyanazine, simazine, simetryn, terbutryne and terbutylazine; triazinones such as, for example, hexazinon, metamitron and metribuzin; others sich as, for example, aminotriazole, benfuresate, bentazone, cinmethylin, clomazone, clopyralid, difenzoquat, dithiopyr, ethofumesate, fluorochloridone, glufosimte, glyphosate, isoxaben, pyridate, quinchlorac, quinmerac, sulfosate and tridiphane. 4-
Amino-N-(1,1-dimethylethyl)-4,5-dihydro-3-(1-methylethyl)-5-oxo0-1H-1,2 4- triazole-1-carboxamide and 2-((((4,5-dihydro-4-methyl-5-0x0-3-propoxy-1H-1,2,4- triazol-1-yl)carbonyl)amino)sulfonyl)-methyl benzoale may also be mentioned.
Examples of plant growth regulators which may be mentioned are chlorocholine chloride and ethephon.
Examples of plant nutrients which may be mentioned are customary inorganic or organic fertilizers for providing plants with macro- and/or micronutrients.
Examples of repellents which may be mentioned are diethyl-tolylamide, ethylhexanediol and butopyronoxyl.
The microcapsules according to the invention comprise one or more oil-soluble dispersants (a4).
Suitable oil-soluble dispersants (ad) are, for example, fatty acids, fatty acid esters and, in particular, fatty acid amides. By way of example, decanecarboxamide and oo -12- dodecanecarboxamide may be mentioned. Highly suitable are also oil-soluble polymers having a molecular weight of from 2000 to 1,000,000. Preference is given to polymers comprising a number of Cg- to Cyx-alkyl (meth)acrylate units and/or vinyl ester units of Cg- to Cp-carboxylic acids in the polymer. By way of example, polymers having stearyl methacrylate, lauryl methacrylate and vinyl stearate units in the polymer may be mentioned. Particularly suitable are copolymers of Cg- to Cos- alkyl (meth)acrylates and/or vinyl esters of Cgs- to Cj-carboxylic acids with hydrophilic monomers. In this context, hydrophilic monomers are to be understood as meaning polymerizable olefinically unsaturated compounds which are fully or partially (more than 2.5% by weight at 20°C) water-soluble. Examples which may be mentioned are: acrylic acid and its alkali metal and ammonium salts, methacrylic acid and its alkali metal and ammonium salts, hydroxyethyl methacrylate, hydroxyethyl acrylate, diethylene glycol monoacrylate, diethylene glycol monomethacrylate, triethylene glycol monoacrylate, triethylene glycol monomethacrylate, tetraethylene glycol monoacrylate, tetraethylene glycol monomethacrylate, glycerol monoacrylate, aminoethyl methacrylate, N,N-dimethylaminoethyl methacrylate, acrylamide, methacrylamide, vinylpyrrolidone and vinylimidazole. Preference is given to aminoethyl methacrylate, N,N-dimethylaminoethyl methacrylate, acrylamide, methacrylamide, vinylpyrrolidone and vinylimidazole.
Particularly preferred oil-soluble dispersants are copolymers of - 75 - 99% by weight of Cg- to Cx-alkyl (meth)acrylate and/or vinyl esters of
Cs- to Cy,-carboxylic acids and - 1 - 25% by weight of hydrophilic monomer from the group consisting of aminoethyl methacrylate, N,N-dimethylaminoethyl methacrylate, acrylamide, methacrylamide, vinylpyrrolidone and vinylimidazole. :
The microcapsules according to the invention may comprise additives (a5) which are conventionally employed as additives in plant treatment products. These include, for example, colors, antioxidants and antifreeze agents.
* »
Suitable colors are soluble colors or sparingly soluble color pigments such as, for example, titanium dioxide, color black or zinc oxide.
Suitable antioxidants are all substances which can conventionally be employed for this purpose in plant treatment products. Sterically hindered phenols and alkyl- substituted hydroxyanisoles and hydroxytoluenes are preferred.
Suitable antifreeze agents are all materials which are conventionally employed for this purpose in plant treatment products. Preference is given to using urea, glycerol or propylene glycol.
The content of the individual components in the microcapsules according to the invention can be varied within a relatively wide range. Thus, the proportions - of envelope (I) are generally between 2 and 20% by weight, preferably between 4 and 16% by weight, : - of continuous solid polymer phase (al) are generally between 10 and 60% by weight, preferably between 20 and 40% by weight, - of liquid oil phase (a2) are generally between 12 and 60% by weight, preferably between 12 and 50% by weight - of agrochemical active ingredients (a3) are generally between 1 and 75% by weight, preferably between 5 and 60% by weight, - of oil-soluble dispersant (a4) are generally between 0.1 and 10% by weight, preferably between 0.2 and 5% by weight, in each case based on the microcapsules, and
} R -14- - of additives are in general between 0 and 20% by weight, preferably between 0 and 5% by weight, based on the sum of (I)-and (ID).
The particle size of the microcapsules according to the invention can be varied within a certain range. It is generally between 1 and 100 pm, preferably between 5 and 50 pm, particularly preferably between 5 and 30 um. The core of the microcapsules according to the invention is preferably multiphasic, particularly preferably triphasic.
Within the microcapsules, the polymer phase preferably forms an open sponge structure, the pores of which are filled by the oil. Most of the active ingredient is present as a finely dispersed phase in the oil phase. :
The microcapsules according to the invention can be present either as solid particles or as a dispersion of solid particles in an aqueous phase.
The microcapsules according to the invention are prepared by dispersing an organic phase of the components mentioned under (A) as fine droplets in an aqueous phase of the components mentioned under (B), by stirring at temperatures between 0°C and 60°C, followed by reaction of the wall-forming components (a7) and (b3) with formation of the microcapsule envelopes and, finally, curing of the monomers (a0) at elevated temperature.
The components (a2) to (a5) required for the organic phase when carrying out the process according to the invention are characterized by the components of these groups listed above.
Suitable monomers (a0) capable of forming a continuous solid phase are those monomers which are suitable for forming the polymers mentioned under (al). Such monomers have already been mentioned in connection with the description of the components (al). :
Moreover, the organic phase also comprises, if appropriate, initiators and catalysts (a6) for curing monomers, and, if appropriate, oil-soluble wall-forming components (a7).
Suitable initiators for curing vinylic monomers are, preferably: peroxy compounds such as dibenzoyl peroxide, dilauryl peroxide, bis(p- chlorobenzoyl peroxide), dicyclohexylperoxy dicarbonate, tert-butyl peroctoate, 2,5- bis-(2-ethylhexanoylperoxy)-2,5-dimethylhexane and tert-amylperoxy-2-ethylhexane, furthermore azo compounds, such as 2,2’-azobis(isobutyronitrile) and 2,2-azobis(2- methylbutyronitrile).
Suitable catalysts for curing isocyanates using di- or polyols to give polyurethanes are, for example, organic tin compounds, such as dibutyltin dilaurate, and tertiary amines, such as triethylamine.
Oil-soluble wall-forming components (a7) are used when it is intended to construct envelopes of polyurea or polyamide. In the case of polyurea, these are the - abovementioned difunctional and multifunctional aromatic or aliphatic isocyanates; in the case of polyamides, these are dicarboxylic acid dichlorides, such as, for example, succinic acid dichloride, sebacic acid dichloride, terephthalic acid dichloride and adipic acid dichloride.
The organic phase is mixed thoroughly, preferably using mills, in particular ball mills and bead mills, the particles of solid agrochemical active ingredients (a3) being comminuted to particle sizes of from 0.1 to 5 um, preferably from 0.2 to 2 um. The resulting homogenized organic phase is generally resistant to settling, i.e. over periods of from minutes to a number of hours, the droplets or particles of active ingredient do not form a sediment.
The organic phase is dispersed as droplets in an aqueous phase. For this purpose, mixers having high shear forces, in particular rapid mixers and rotor stator mixers,
. v are used. Here, the size of the droplets formed is from 1 to 100 um, preferably from 5 to 50 um, particularly preferably from S to 30 pm. The particle size can be adjusted via the amount of the shear forces or the speed of the stirrer or mixer.
The aqueous phase comprises at least one water-soluble dispersant (b2). Suitable dispersants are generally all substances which can be employed for this purpose. By way of preference, mention may be made of natural and synthetic water-soluble polymers such as gelatin, starch and cellulose derivatives, in particular cellulose esters and cellulose ethers, furthermore polyvinyl alcohol, polyvinyl pyrrolidone, polyacrylic acid, polymethacrylic acid and copolymers of (meth)acrylic acid and (meth)acrylic acid esters and lignosulfonic acid. Highly suitable are also mixtures of different dispersants, for example mixtures of polyvinyl alcohol and sodium lignosulfonate. The amount of dispersant is generally from 0.2 to 10% by weight, preferably from 0.5 to 5% by weight, based on the aqueous phase.
The aqueous phase comprises at least one water-soluble wall-forming component (b3). These are to be understood as meaning substances which, by physical precipitation or chemical reaction, if appropriate in combination with the oil-soluble wall-forming component (a7), form a polymer at the interface between organic phase and aqueous phase.
Polymers which are particularly suitable according to the invention for the envelope are polyureas, polyamides, gelatins and formaldehyde resins.
To prepare polyurea envelopes and polyamide envelopes, diamines or polyamines which react with isocyanates or dicarboxylic acid dichlorides from the organic phase to give polyureas or polyamides are added to the aqueous phase. A diamine which may be given particular mention is ethylenediamine. Preferred polyamines are diethylenetriamine and triethylenetetramine. Particularly dense envelopes are obtained when polyamines are used to at least some extent. For this reaction, a temperature of from 20 to 80°C, preferably from 40 to 60°C, is used. The reaction time is from 0.5 to 5 hours.
When preparing gelatin-containing envelopes, gelatin is dissolved in the aqueous phase in basic or neutral medium at a temperature above the gelling temperature of 37°C, for example at 40°C, an anionic polymer is added to form a coacervate, the pH is adjusted to between 3.5 and 5.0, for example by adding citric acid, and the mixture is cooled to temperatures between 0°C and 20°C. :
Here, suitable anionic polymers are both natural polymers, such as gum arabic, and synthetic polymers. Suitable synthetic anionic polymers are copolymers which have 10 . been made alkaline and contain units of, for example, maleic acid, acrylic acid, methacrylic acid, acrylamide, methacrylamide and/or carboxymethylcellulose.
Gelatin-containing capsules can be cured using customary curing agents, such as, for example, formaldehyde or glutaraldehyde, where the pH is adjusted to an alkaline pH to achieve efficient curing. Formation and curing of the gelatin envelope generally takes a plurality of hours.
To form envelopes of formaldehyde resins, formaldehyde and phenolic and/or aminic reactive components are added to the aqueous phase. Here, suitable phenolic reactive components are, for example, phenol, resorcinol and catechol. Examples of aminic reactive components are urea, melamine and ammonia-formaldehyde condensates, such as hexamethylenetetramine. The formaldehyde resins are formed at elevated temperature of, for example, from 50 to 90°C, at an acidic pH.
During curing of the monomers in step (D) of the process according to the invention, the temperature can be varied within a certain range. In general, curing is carried out at temperatures between 60°C and 100°C, preferably between 70°C and 100°C.
Curing takes from 1 hour to a plurality of hours. In this reaction step, the speed of the stirrer is not critical. Slow stirrer speeds sufficient to keep the capsules formed suspended are sufficient.
After curing, the microcapsules can remain in the dispersion or be isolated by customary methods, for example by filtration or decanting and, if appropriate after one or more washing steps, be dried. :
The microcapsules according to the invention are highly suitable for applying agrochemical active ingredients to plants and/or their habitat. They ensure the release of the active components in the respective desired amount over a relatively long period of time. Moreover, they have high mechanical stability.
The microcapsules according to the invention can be used as such either in solid form or as suspensions, if appropriate after prior dilution with water, in practice. Here, application is carried out by customary methods, i.e. for example by watering, spraying, atomizing or broadcasting.
The application rate of the microcapsule formulations according to the invention can be varied within a relatively wide range. It depends on the agrochemical active ingredients in question and their content in the microcapsules.
The invention is illustrated by the examples below.
t wv
Preparation Examples
Example 1 5S a) Dispersion of active ingredient
At a temperature in between 30°C and 40°C, a mixture of 750 g of imidacloprid, 1550 g of mineral oil (technical white oil Enerpar T 017), 188 g of alkylaryl polyglycol ether and 2.5 g of antifoam (silicone material) is ground in a bead mill for 3 hours. A sedimentation-resistant dispersion in which 90% of the active ingredient particles have a particle size between 1 and 4 yum is formed. b) Microcapsules 1S Atroom temperature, 102 g of the dispersion from a), 27.1 g of stearyl methacrylate, 3.0 g of hexamethylene dimethacrylate, 0.3 g of 2,2'-azobis(2-methylbutyronitrile), : 4.9 g of toluene diisocyanate and 3.7 g of 4,4"-methylenebis(cyclohexyl isocyanate) are mixed intensively. At room temperature, this mixture is emulsified in a solution of 205 g of deionized water, 1.8 g of polyvinyl alcohol (Mowiol 26-88) and 5.3 g of lignosulfonate (Borresperse Na) using a rotor stator mixer (Silverson LAR). The resulting emulsion is transferred into a stirred reactor. The present mixture is mixed with 5.8 g of a 50% strength aqueous solution of diethylene triamine. The stirrer speed is set to 350 rotations per minute. Over a period of 1 hour, the temperature is increased from room temperature to 55°C, and is then kept at 55°C for 2 hours. The mixture is then heated to 60°C and this temperature is kept for 4 hours. This gives 350 g of a dispersion of microcapsules; the particle size is from 2 to 25 um; the content of active ingredient is 8.4% by weight.
Example 2 a) Dispersion of active ingredient
Ata temperature in between 30°C and 40°C, a mixture of 760 g of 2-((((4,5-dihydro- 4-methyl-4-oxo0-3-propoxy-1H-1,2 4-triazol-1-yl)carbonyl)amino)sulfonyl)-methyl benzoate sodium salt, 1550 g of mineral oil (technical white oil Enerpar T 017), 188 g of alkylaryl polyglycol ether and 2.5 g of antifoam (silicone material) is ground in a bead mill for 3 hours. A sedimentation-resistant dispersion in which 90% of the active ingredient particles have a particle size between 1 and 4 um is formed. b) Microcapsules
At room temperature, 102 g of the dispersion from a), 27.1 g of stearyl methacrylate, 3.0 g of hexamethylene dimethacrylate, 0.3 g of 2,2'-azobis(2-methylbutyronitrile), 4.9 g of toluene diisocyanate and 3.7 g of 4,4-methylenebis(cyclohexyl isocyanate) are mixed intensively. At room temperature, this mixture is emulsified in a solution of 205 g of deionized water, 1.8 g of polyvinyl alcohol (Mowiol 26-88) and 5.3 g of lignosulfonate (Borresperse Na) using a rotor stator mixer (Silverson L4R). The resulting emulsion is transferred into a stirred reactor. The present mixture is mixed with 5.8 g of a 50% strength aqueous solution of diethylene triamine. The stirrer speed is set to 350 rotations per minute. Over a period of 1 hour, the temperature is increased from room temperature to 55°C, and is then kept at 55°C for 2 hours. The mixture is then heated to 60°C and this temperature is kept for 4 hours. This gives 350 g of a dispersion of microcapsules; the particle size is from 2 to 10 um; the content of active ingredient is 7.5% by weight.
Example 3 a) Dispersion of active ingredient
At a temperature in between 30°C and 40°C, a mixture of 760 g of tebuconazole, 1550 g of mineral oil (technical white oil Enerpar T 017), 188 g of alkylaryl polyglycol ether and 2.5 g of antifoam (silicone material) is ground in a bead mill for 3 hours. A sedimentation-resistant dispersion in which 90% of the active ingredient particles have a particle size between 1 and 4 um is formed. b) Microcapsules
At room temperature, 102 g of the dispersion from a), 27.1 g of stearyl methacrylate, 3.0 g of hexamethylene dimethacrylate, 0.3 g of 2,2'-azobis(2-methylbutyronitrile), 4.9 g of toluene diisocyanate and 3.7 g of 4,4'-methylenebis(cyclohexyl isocyanate) are mixed intensively. At room temperature, this mixture is emulsified in a solution of 205 g of deionized water, 1.8 g of polyvinyl alcohol (Mowiol 26-88) and 5.3 g of lignosulfonate (Borresperse Na) using a rotor stator mixer (Silverson L4R). The resulting emulsion is transferred into a stirred reactor. The present mixture is mixed with 5.8 g of a 50% strength aqueous solution of diethylene triamine. The stirrer speed is set to 350 rotations per minute. Over a period of 1 hour, the temperature is increased from room temperature to 55°C, and is then kept at 55°C for 2 hours. The mixture is then heated to 60°C and this temperature is kept for 4 hours. This gives 350 g of a dispersion of microcapsules; the particle size is from 2 to 10 um; the content of active ingredient is 8.5% by weight.
Example 4 a) Dispersion of active ingredient
At a temperature in between 30°C and 40°C, a mixture of 760 g of dichlobenil, 1550 g of mineral oil (technical white oil Enerpar T 017), 188 g of alkylaryl polyglycol ether and 2.5 g of antifoam (silicone material) is ground in a bead mill for 3 hours. A sedimentation-resistant dispersion in which 90% of the active ingredient particles have a particle size between 1 and 4 ym is formed. b) Microcapsules
At room temperature, 102 g of the dispersion from a), 27.1 g of stearyl methacrylate, 3.0 g of hexamethylene dimethacrylate, 0.3 g of 2,2-azobis(2-methylbutyronitrile), 4.9 g of toluene diisocyanate and 3.7 g of 4,4"-methylenebis(cyclohexyl isocyanate) are mixed intensively. At room temperature, this mixture is emulsified in a solution of 205 g of deionized water, 1.8 g of polyvinyl alcohol (Mowiol 26-88) and 5.3 g of lignosulfonate (Borresperse Na) using a rotor stator mixer (Silverson L4R). The resulting emulsion is transferred into a stirred reactor. The present mixture is mixed with 5.8 g of a 50% strength aqueous solution of diethylene triamine. The stirrer speed is set to 350 rotations per minute. Over a period of 1 hour, the temperature is increased from room temperature to 55°C, and is then kept at 55°C for 2 hours. The mixture is then heated to 60°C and this temperature is kept for 4 hours. This gives 350 g of a dispersion of microcapsules; the particle size is from 2 to 20 um; the content of active ingredient is 8.5% by weight.
Example 5 a) Dispersion of active ingredient :
At a temperature in between 30°C and 40°C, a mixture of 760 g of tebuconazole, 1550 g of mineral oil (technical white oil Enerpar T 017), 188 g of alkylaryl polyglycol ether and 2.5 g of antifoam (silicone material) is ground in a bead mill for 3 hours. A sedimentation-resistant dispersion in which 90% of the active ingredient particles have a particle size between 1 and 4 um is formed. b) Microcapsules
At room temperature, 107 g of the dispersion from a), 28.1 g of stearyl methacrylate, 3.1 g of hexamethylene dimethacrylate, 0.3 g of 2,2'-azobis(2-methylbutyronitrile), 2.5 g of toluene diisocyanate and 1.8 g of 4,4-methylenebis(cyclohexyl isocyanate) are mixed intensively. At room temperature, this mixture is emulsified in a solution of 205 g of deionized water, 1.8 g of polyvinyl alcohol (Mowiol 26-88) and 5.3 g of lignosulfonate (Borresperse Na) using a rotor stator mixer (Silverson IL4R). The resulting emulsion is transferred into a stirred reactor. The present mixture is mixed with 5.8 g of a 50% strength aqueous solution of diethylene triamine. The stirrer speed is set to 350 rotations per minute. Over a period of 1 hour, the temperature is increased from room temperature to 55°C, and is then kept at 55°C for 2 hours. The mixture is then heated to 60°C and this temperature is kept for 4 hours. This gives 350 g of a dispersion of microcapsules; the particle size is from 2 to 10 um; the content of active ingredient is 8.5% by weight.
Example 6 a) Dispersion of active ingredient
At a temperature in between 30°C and 40°C, a mixture of 760 g of thiacloprid, 1550 g of mineral oil (technical white oil Enerpar T 017), 188 g of alkylaryl polyglycol ether and 2.5 g of antifoam (silicone material) is ground in a bead mill for 3 hours. A sedimentation-resistant dispersion in which 90% of the active ingredient particles have a particle size between 1 and 4 ym is formed. b) Microcapsules
At room temperature, 107 g of the dispersion from a), 28.1 g of stearyl methacrylate, 3.1 g of hexamethylene dimethacrylate, 0.3 g of 2,2'-azobis(2-methylbutyronitrile), 2.5 g of toluene diisocyanate and 1.8 g of 4,4'-methylenebis(cyclohexyl isocyanate) are mixed intensively. At room temperature, this mixture is emulsified in a solution of 205 g of deionized water, 1.8 g of polyvinyl alcohol (Mowiol 26-88) and 5.3 g of lignosulfonate (Borresperse Na) using a rotor stator mixer (Silverson LAR). The resulting emulsion is transferred into a stirred reactor. The present mixture is mixed with 5.8 g of a 50% strength aqueous solution of diethylene triamine. The stirrer speed is set to 350 rotations per minute. Over a period of 1 hour, the temperature is increased from room temperature to 55°C, and is then kept at 55°C for 2 hours. The mixture is then heated to 60°C and this temperature is kept for 4 hours. This gives 350 g of a dispersion of microcapsules; the particle size is from 2 to 30 um; the content of active ingredient is 8.5% by weight.
Example 7 a) Dispersion of active ingredient
At a temperature in between 30°C and 40°C, a mixture of 760 g of tebuconazole, 1550 g of mineral oil (technical white oil Enerpar T 017), 188 g of alkylaryl polyglycol ether and 2.5 g of antifoam (silicone material) is ground in a bead mill for 3 hours. A sedimentation-resistant dispersion in which 90% of the active ingredient particles have a particle size between 1 and 4 pm is formed. b) Microcapsules
At room temperature, 102 g of the dispersion from a), 28 g of polybutadienediol (R 45 HT), 0.7 g of bis(neodecanoyloxy)dioctylstannane (Fomrez UL-38), 6.2 g of toluene diisocyanate and 4.7 g of 4,4'-methylenebis(cyclohexyl isocyanate) are mixed intensively. At room temperature, this mixture is emulsified in a solution of 205 g of deionized water, 1.9 g of polyvinyl alcohol (Mowiol 26-88) and 5.7g of lignosulfonate (Borresperse Na) using a rotor stator mixer (Silverson 14R). The resulting emulsion is transferred into a stirred reactor. The present mixture is mixed with 5.9 g of a 50% strength aqueous solution of diethylene triamine. The stirrer speed is set to 350 rotations per minute. Over a period of 1.5 hours, the temperature is increased from room temperature to 55°C, and is then kept at 55°C for 1.5 hours.
The mixture is then heated to 60°C and this temperature is kept for 4 hours. This gives 350 g of a dispersion of microcapsules; the particle size is from 3 to 40 um; the content of active ingredient is 8.4% by weight.
Example 8 a) Dispersion of active ingredient
At a temperature in between 30°C and 40°C, a mixture of 760 g of dichlobenil, 1550 g of mineral oil (technical white oil Enerpar T 017), 188 g of alkylaryl polyglycol ether and 2.5 g of antifoam (silicone material) is ground in a bead mill for 3 hours. A sedimentation-resistant dispersion in which 90% of the active ingredient particles have a particle size between 1 and 4 um is formed. b) Microcapsules
At room temperature, 102 g of the dispersion from a), 28 g of polybutadienediol (R 45 HT), 0.7 g of bis(neodecanoyloxy)dioctylstannane (Fomrez UL-38), 6.2 g of toluene diisocyanate and 4.7 g of 4,4'-methylenebis(cyclohexy! isocyanate) are mixed intensively. At room temperature, this mixture is emulsified in a solution of 205 g of deionized water, 1.9 g of polyvinyl alcohol (Mowiol 26-88) and 5.7g of lignosulfonate (Borresperse Na) using a rotor stator mixer (Silverson L4R). The resulting emulsion is transferred into a stirred reactor. The present mixture is mixed with 5.9 g of a 50% strength aqueous solution of diethylene triamine. The stirrer speed is set to 350 rotations per minute. Over a period of 1.5 hours, the temperature is increased from room temperature to 55°C, and is then kept at 55°C for 1.5 hours.
The mixture is then heated to 60°C and this temperature is kept for 4 hours. This gives 350 g of a dispersion of microcapsules; the particle size is from 7 to 90 ym; the content of active ingredient is 8.5% by weight.
X . -27-
Example 9 a) Dispersion of active ingredient
At a temperature in between 30°C and 40°C, a mixture of 760 g of thiacloprid, 1550 g of mineral oil (technical white oil Enerpar T 017), 188 g of alkylaryl polyglycol ether and 2.5 g of antifoam (silicone material) is ground in a bead mill for 3 hours. A sedimentation-resistant dispersion in which 90% of the active ingredient particles have a particle size between 1 and 4 um is formed. b) Microcapsules
At room temperature, 102 g of the dispersion from a), 28 g of polybutadienediol (R 45 HT), 0.7 g of bis(neodecanoyloxy)dioctylstannane (Fomrez UL-38), 6.2 g of toluene diisocyanate and 4.7 g of 4,4"-methylenebis(cyclohexyl isocyanate) are mixed intensively. At room temperature, this mixture is emulsified in a solution of 205 g of deionized water, 1.9 g of polyvinyl alcohol (Mowiol 26-88) and 5.7g of lignosulfonate (Borresperse Na) using a rotor stator mixer (Silverson L4R). The resulting emulsion is transferred into a stirred reactor. The present mixture is mixed with 59 g of a 50% strength aqueous solution of diethylene triamine. The stirrer speed is set to 350 rotations per minute. Over a period of 1.5 hours, the temperature is increased from room temperature to 55°C, and is then kept at 55°C for 1.5 hours. : The mixture is then heated to 60°C and this temperature is kept for 4 hours. This gives 350 g of a dispersion of microcapsules; the particle size is from 3 to 45 um; the content of active ingredient is 8.5% by weight.
Claims (12)
1. A microcapsule, consisting of D an envelope produced from a polymer material and II) an envelope content of al) a continuous solid polymer phase, a2) a liquid oil phase, a3) at least one agrochemical active ingredient and a4) at least one oil-soluble dispersant, where the content of the agrochemical active ingredient, based on the overall weight of the capsules, ranges between 1 and 75% by weight.
2. A microcapsule as claimed in claim 1, characterized in that the envelope content includes a5) additives
3. A microcapsule as claimed in claim 1 or claim 2, characterized in that the agrochemical active ingredient (a3) contained therein is a fungicide, bactericide, insecticide, acaricide, nematicide, molluscicide, herbicide, plant growth regulator, plant nutrient or a repellent.
4, A microcapsule as claimed in any one of claims 1 to 3, characterized in that the envelope (I) consists of polyurea.
5. A microcapsule as claimed in any one of claims 1 to 4, characterized in that the envelope (I) consists of gelatin, hardened gelatin or gelatin complex coacervate.
6. A microcapsule as claimed in any one of claims 1 to 5, characterized in that the continuous solid polymer phase (al) consists of polymerized units of vinyl monomers and crosslinkers. AMENDED SHEET
0 * [9 e -3 1-
7. A microcapsule as claimed in any one of claims 1 to 6, characterized in that the continuous solid polymer phase (al) consists of polyurethane.
8. A process for preparing microcapsules as claimed in claim 1, characterized in that A) an organic phase of a0) monomers capable of forming a continuous solid polymer phase, a2) aliquid oil phase, a3) at least one agrochemical active ingredient and a4) at least one oil-soluble dispersant B) in an aqueous phase of bl) water, b2) at least one water-soluble dispersant and b3) at least one water-soluble wall-forming component 1s, with stirring at temperatures between 0°C and 60°C, dispersed into fine droplets, Cc) then allowed to react with formation of microcapsules and D) then allowed to cure at elevated temperature.
9. A process as claimed in claim 8, characterized in that the organic phase includes ab) additives. : AMENDED SHEET yg » v 4
10. A process as claimed in claim 8 or claim 9, characterized in that the organic phase includes a6) initiators and catalysts.
11. A process as claimed in any one of claims 8 to 10, characterized in that the organic phase includes a7) at least one oil-soluble wall-forming component,
12. The use of microcapsules as claimed in claim 1 for applying agrochemical active ingredients to plants and/or their habitat. AMENDED SHEET
Applications Claiming Priority (1)
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DE19947147A DE19947147A1 (en) | 1999-10-01 | 1999-10-01 | Microcapsule for application of agrochemicals comprises polymer shell enclosing continuous solid polymer, liquid oil phase, agrochemical and oil-soluble dispersant |
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ZA200201468B true ZA200201468B (en) | 2003-04-30 |
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ZA200201468A ZA200201468B (en) | 1999-10-01 | 2002-02-21 | Microcapsules. |
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EP (1) | EP1221838A1 (en) |
JP (1) | JP2003517464A (en) |
KR (1) | KR20020029123A (en) |
CN (1) | CN1377227A (en) |
AU (1) | AU7421100A (en) |
BR (1) | BR0014674A (en) |
CA (1) | CA2385991A1 (en) |
DE (1) | DE19947147A1 (en) |
IL (1) | IL148410A0 (en) |
MX (1) | MXPA02003256A (en) |
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ZA (1) | ZA200201468B (en) |
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DE10117784A1 (en) * | 2001-04-10 | 2002-10-17 | Bayer Ag | Microcapsule, for containing core of active substance especially plant protection agent, has shell of polyurethane or polyurea and is free of liquid |
DE10223916A1 (en) | 2002-05-29 | 2003-12-11 | Bayer Cropscience Ag | Microcapsule formulations |
ES2572162T3 (en) * | 2002-06-19 | 2016-05-30 | Thor Gmbh | Coating mass with biocide microcapsules |
DE10359792A1 (en) * | 2003-12-19 | 2005-07-21 | Bayer Technology Services Gmbh | Multiphasic drug formulation |
CN100444732C (en) * | 2004-03-22 | 2008-12-24 | 侯金荣 | Prepn process of plant pesticide with natural avermectin microcapsule |
CN100444733C (en) * | 2004-03-22 | 2008-12-24 | 侯金荣 | Plant pesticide with natural avermection microcapsule and its application |
EP1795071A1 (en) * | 2005-12-07 | 2007-06-13 | Incotec International B.V. | Modified active-ingredient-containing pellets/capsules |
GB0526416D0 (en) | 2005-12-23 | 2006-02-08 | Syngenta Ltd | Formulation |
CA2690070A1 (en) * | 2007-06-21 | 2008-12-24 | Syngenta Participations Ag | Method of improving the growth of a plant |
JP5603645B2 (en) * | 2009-04-30 | 2014-10-08 | 日本エンバイロケミカルズ株式会社 | Microcapsule and method for producing the same |
JP5439952B2 (en) * | 2009-05-29 | 2014-03-12 | 住友化学株式会社 | Method for producing microcapsules |
CN103037688A (en) * | 2010-06-07 | 2013-04-10 | 陶氏益农公司 | Microcapsule suspensions including high levels of agriculturally active ingredients |
JP5763570B2 (en) * | 2011-03-11 | 2015-08-12 | 大阪ガスケミカル株式会社 | Sustained release particles and method for producing the same |
CN102239831A (en) * | 2011-05-03 | 2011-11-16 | 谭晓辉 | Lythidathion microcapsule suspending agent and preparation method |
CN106070275A (en) * | 2016-06-03 | 2016-11-09 | 安徽广信农化股份有限公司 | The method of the pyraclostrobin microcapsule of preparation uniform particle size |
CN108575993A (en) * | 2018-04-19 | 2018-09-28 | 河北威远生物化工有限公司 | A kind of dispersible micro-capsule oil-suspending agent of glufosinate-ammonium and preparation method thereof |
CN110876378A (en) * | 2019-12-11 | 2020-03-13 | 利民化学有限责任公司 | Intelligent microcapsule suspending agent and preparation method thereof |
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DE2757017C3 (en) * | 1977-12-21 | 1986-07-31 | Hoechst Ag, 6230 Frankfurt | Process for the production of pressure-resistant polyurethane-polyurea capsules with a structured inner mass |
DE3020781C2 (en) * | 1980-05-31 | 1982-11-18 | Hoechst Ag, 6000 Frankfurt | Pressure-resistant microcapsules with a polyamide outer shell and an inner mass structured by polyurethane-polyurea or polyurea and process for their production |
US4681806A (en) * | 1986-02-13 | 1987-07-21 | Minnesota Mining And Manufacturing Company | Particles containing releasable fill material and method of making same |
US4727011A (en) * | 1986-10-16 | 1988-02-23 | Xerox Corporation | Processes for encapsulated toner compositions with interfacial/free-radical polymerization |
US5225278A (en) * | 1987-08-26 | 1993-07-06 | Rohm And Haas Company | Process for microencapsulation |
DE69411583T2 (en) * | 1993-11-15 | 1999-02-18 | Zeneca Ltd | MICROCAPSULES CONTAINING SUSPENSIONS FROM BIOLOGICALLY ACTIVE COMPOUNDS |
JPH09110621A (en) * | 1995-10-12 | 1997-04-28 | Dai Ichi Kogyo Seiyaku Co Ltd | Termite controlling agent and dispersion containing the same |
JP3822288B2 (en) * | 1996-09-12 | 2006-09-13 | 第一工業製薬株式会社 | Acaricide and acaricide-containing dispersion containing the same |
-
1999
- 1999-10-01 DE DE19947147A patent/DE19947147A1/en not_active Withdrawn
-
2000
- 2000-09-19 BR BR0014674-9A patent/BR0014674A/en not_active Application Discontinuation
- 2000-09-19 EP EP00962517A patent/EP1221838A1/en not_active Withdrawn
- 2000-09-19 JP JP2001527645A patent/JP2003517464A/en active Pending
- 2000-09-19 KR KR1020027003001A patent/KR20020029123A/en not_active Application Discontinuation
- 2000-09-19 CA CA002385991A patent/CA2385991A1/en not_active Abandoned
- 2000-09-19 IL IL14841000A patent/IL148410A0/en unknown
- 2000-09-19 CN CN00813683A patent/CN1377227A/en active Pending
- 2000-09-19 MX MXPA02003256A patent/MXPA02003256A/en unknown
- 2000-09-19 WO PCT/EP2000/009268 patent/WO2001024631A1/en not_active Application Discontinuation
- 2000-09-19 AU AU74211/00A patent/AU7421100A/en not_active Abandoned
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2002
- 2002-02-21 ZA ZA200201468A patent/ZA200201468B/en unknown
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AU7421100A (en) | 2001-05-10 |
IL148410A0 (en) | 2002-09-12 |
DE19947147A1 (en) | 2001-04-05 |
MXPA02003256A (en) | 2002-10-31 |
WO2001024631A1 (en) | 2001-04-12 |
KR20020029123A (en) | 2002-04-17 |
JP2003517464A (en) | 2003-05-27 |
CN1377227A (en) | 2002-10-30 |
CA2385991A1 (en) | 2001-04-12 |
BR0014674A (en) | 2002-06-11 |
EP1221838A1 (en) | 2002-07-17 |
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