WO2010137743A1 - Method for producing microcapsule - Google Patents
Method for producing microcapsule Download PDFInfo
- Publication number
- WO2010137743A1 WO2010137743A1 PCT/JP2010/059489 JP2010059489W WO2010137743A1 WO 2010137743 A1 WO2010137743 A1 WO 2010137743A1 JP 2010059489 W JP2010059489 W JP 2010059489W WO 2010137743 A1 WO2010137743 A1 WO 2010137743A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- mixture
- microcapsule
- volume
- particles
- referred
- Prior art date
Links
- 239000003094 microcapsule Substances 0.000 title claims abstract description 282
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 37
- 239000000203 mixture Substances 0.000 claims abstract description 346
- 150000001875 compounds Chemical class 0.000 claims abstract description 145
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 83
- 230000000361 pesticidal effect Effects 0.000 claims abstract description 76
- 239000007788 liquid Substances 0.000 claims abstract description 33
- 239000005056 polyisocyanate Chemical group 0.000 claims abstract description 33
- 229920001228 polyisocyanate Chemical group 0.000 claims abstract description 33
- 238000000034 method Methods 0.000 claims abstract description 28
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 18
- 239000004814 polyurethane Substances 0.000 claims abstract description 18
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 15
- 229920000768 polyamine Polymers 0.000 claims abstract description 15
- 229920005862 polyol Polymers 0.000 claims abstract description 14
- 150000003077 polyols Chemical class 0.000 claims abstract description 14
- 229920002396 Polyurea Polymers 0.000 claims abstract description 9
- 229920003226 polyurethane urea Polymers 0.000 claims abstract description 6
- 239000005888 Clothianidin Substances 0.000 claims description 102
- 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 87
- 239000007787 solid Substances 0.000 claims description 20
- XEOSKTHOPLADLN-QTJNJRLBSA-N acetyl (z,12r)-12-hydroxyoctadec-9-enoate Chemical compound CCCCCC[C@@H](O)C\C=C/CCCCCCCC(=O)OC(C)=O XEOSKTHOPLADLN-QTJNJRLBSA-N 0.000 claims description 3
- -1 fatty acid ester Chemical class 0.000 abstract description 20
- 235000014113 dietary fatty acids Nutrition 0.000 abstract description 5
- 239000000194 fatty acid Substances 0.000 abstract description 5
- 229930195729 fatty acid Natural products 0.000 abstract description 5
- 230000001934 delay Effects 0.000 abstract 1
- 239000002245 particle Substances 0.000 description 273
- 239000011369 resultant mixture Substances 0.000 description 106
- 239000007900 aqueous suspension Substances 0.000 description 59
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 49
- 239000003795 chemical substances by application Substances 0.000 description 34
- 239000008346 aqueous phase Substances 0.000 description 30
- 239000003755 preservative agent Substances 0.000 description 24
- 230000002335 preservative effect Effects 0.000 description 24
- 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 18
- GUUULVAMQJLDSY-UHFFFAOYSA-N 4,5-dihydro-1,2-thiazole Chemical class C1CC=NS1 GUUULVAMQJLDSY-UHFFFAOYSA-N 0.000 description 17
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 17
- 244000215068 Acacia senegal Species 0.000 description 16
- 229920000084 Gum arabic Polymers 0.000 description 16
- 239000000205 acacia gum Substances 0.000 description 16
- 235000010489 acacia gum Nutrition 0.000 description 16
- 239000008367 deionised water Substances 0.000 description 16
- 229910021641 deionized water Inorganic materials 0.000 description 16
- 239000011521 glass Substances 0.000 description 16
- PGOOBECODWQEAB-FIBGUPNXSA-N 2-[(2-chloro-1,3-thiazol-5-yl)methyl]-1-nitro-3-(trideuteriomethyl)guanidine Chemical group [2H]C([2H])([2H])NC(N[N+]([O-])=O)=NCC1=CN=C(Cl)S1 PGOOBECODWQEAB-FIBGUPNXSA-N 0.000 description 15
- 239000003921 oil Substances 0.000 description 15
- 235000019198 oils Nutrition 0.000 description 15
- 230000002093 peripheral effect Effects 0.000 description 15
- CMOYPQWMTBSLJK-KAMYIIQDSA-N Methyl acetyl ricinoleate Chemical compound CCCCCCC(OC(C)=O)C\C=C/CCCCCCCC(=O)OC CMOYPQWMTBSLJK-KAMYIIQDSA-N 0.000 description 14
- 238000009472 formulation Methods 0.000 description 13
- 229920002635 polyurethane Polymers 0.000 description 12
- CMOYPQWMTBSLJK-ACQXMXPUSA-N methyl (z,12r)-12-acetyloxyoctadec-9-enoate Chemical compound CCCCCC[C@@H](OC(C)=O)C\C=C/CCCCCCCC(=O)OC CMOYPQWMTBSLJK-ACQXMXPUSA-N 0.000 description 10
- 230000000052 comparative effect Effects 0.000 description 8
- 238000002156 mixing Methods 0.000 description 8
- 238000000227 grinding Methods 0.000 description 7
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 229940009868 aluminum magnesium silicate Drugs 0.000 description 6
- WMGSQTMJHBYJMQ-UHFFFAOYSA-N aluminum;magnesium;silicate Chemical compound [Mg+2].[Al+3].[O-][Si]([O-])([O-])[O-] WMGSQTMJHBYJMQ-UHFFFAOYSA-N 0.000 description 6
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 6
- 229920001285 xanthan gum Polymers 0.000 description 6
- 239000000230 xanthan gum Substances 0.000 description 6
- 235000010493 xanthan gum Nutrition 0.000 description 6
- 229940082509 xanthan gum Drugs 0.000 description 6
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 5
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 241000238631 Hexapoda Species 0.000 description 4
- 239000006185 dispersion Substances 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- 230000001105 regulatory effect Effects 0.000 description 4
- 239000002562 thickening agent Substances 0.000 description 4
- ULQISTXYYBZJSJ-UHFFFAOYSA-N 12-hydroxyoctadecanoic acid Chemical compound CCCCCCC(O)CCCCCCCCCCC(O)=O ULQISTXYYBZJSJ-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 238000010790 dilution Methods 0.000 description 3
- 239000012895 dilution Substances 0.000 description 3
- BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 description 3
- 230000000749 insecticidal effect Effects 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 239000005898 Fenoxycarb Substances 0.000 description 2
- 241000607479 Yersinia pestis Species 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 239000011324 bead Substances 0.000 description 2
- DMSMPAJRVJJAGA-UHFFFAOYSA-N benzo[d]isothiazol-3-one Chemical compound C1=CC=C2C(=O)NSC2=C1 DMSMPAJRVJJAGA-UHFFFAOYSA-N 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- TWFZGCMQGLPBSX-UHFFFAOYSA-N carbendazim Chemical compound C1=CC=C2NC(NC(=O)OC)=NC2=C1 TWFZGCMQGLPBSX-UHFFFAOYSA-N 0.000 description 2
- CRQQGFGUEAVUIL-UHFFFAOYSA-N chlorothalonil Chemical compound ClC1=C(Cl)C(C#N)=C(Cl)C(C#N)=C1Cl CRQQGFGUEAVUIL-UHFFFAOYSA-N 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 230000003111 delayed effect Effects 0.000 description 2
- ZPWVASYFFYYZEW-UHFFFAOYSA-L dipotassium hydrogen phosphate Chemical compound [K+].[K+].OP([O-])([O-])=O ZPWVASYFFYYZEW-UHFFFAOYSA-L 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- HJUFTIJOISQSKQ-UHFFFAOYSA-N fenoxycarb Chemical compound C1=CC(OCCNC(=O)OCC)=CC=C1OC1=CC=CC=C1 HJUFTIJOISQSKQ-UHFFFAOYSA-N 0.000 description 2
- 230000000855 fungicidal effect Effects 0.000 description 2
- 230000012010 growth Effects 0.000 description 2
- 230000002363 herbicidal effect Effects 0.000 description 2
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- KRTSDMXIXPKRQR-AATRIKPKSA-N monocrotophos Chemical compound CNC(=O)\C=C(/C)OP(=O)(OC)OC KRTSDMXIXPKRQR-AATRIKPKSA-N 0.000 description 2
- 150000002903 organophosphorus compounds Chemical class 0.000 description 2
- 230000008635 plant growth Effects 0.000 description 2
- 229920006264 polyurethane film Polymers 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 230000001846 repelling effect Effects 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
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- 239000006228 supernatant Substances 0.000 description 2
- 229920001059 synthetic polymer Polymers 0.000 description 2
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 1
- YNWVFADWVLCOPU-MDWZMJQESA-N (1E)-1-(4-chlorophenyl)-4,4-dimethyl-2-(1H-1,2,4-triazol-1-yl)pent-1-en-3-ol Chemical compound C1=NC=NN1/C(C(O)C(C)(C)C)=C/C1=CC=C(Cl)C=C1 YNWVFADWVLCOPU-MDWZMJQESA-N 0.000 description 1
- XERJKGMBORTKEO-VZUCSPMQSA-N (1e)-2-(ethylcarbamoylamino)-n-methoxy-2-oxoethanimidoyl cyanide Chemical compound CCNC(=O)NC(=O)C(\C#N)=N\OC XERJKGMBORTKEO-VZUCSPMQSA-N 0.000 description 1
- UDPGUMQDCGORJQ-UHFFFAOYSA-N (2-chloroethyl)phosphonic acid Chemical compound OP(O)(=O)CCCl UDPGUMQDCGORJQ-UHFFFAOYSA-N 0.000 description 1
- ZMYFCFLJBGAQRS-IAGOWNOFSA-N (2S,3R)-epoxiconazole Chemical compound C1=CC(F)=CC=C1[C@]1(CN2N=CN=C2)[C@@H](C=2C(=CC=CC=2)Cl)O1 ZMYFCFLJBGAQRS-IAGOWNOFSA-N 0.000 description 1
- LDVVMCZRFWMZSG-OLQVQODUSA-N (3ar,7as)-2-(trichloromethylsulfanyl)-3a,4,7,7a-tetrahydroisoindole-1,3-dione Chemical compound C1C=CC[C@H]2C(=O)N(SC(Cl)(Cl)Cl)C(=O)[C@H]21 LDVVMCZRFWMZSG-OLQVQODUSA-N 0.000 description 1
- XUNYDVLIZWUPAW-UHFFFAOYSA-N (4-chlorophenyl) n-(4-methylphenyl)sulfonylcarbamate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC(=O)OC1=CC=C(Cl)C=C1 XUNYDVLIZWUPAW-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 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 1
- IQVNEKKDSLOHHK-FNCQTZNRSA-N (E,E)-hydramethylnon Chemical compound N1CC(C)(C)CNC1=NN=C(/C=C/C=1C=CC(=CC=1)C(F)(F)F)\C=C\C1=CC=C(C(F)(F)F)C=C1 IQVNEKKDSLOHHK-FNCQTZNRSA-N 0.000 description 1
- XGWIJUOSCAQSSV-XHDPSFHLSA-N (S,S)-hexythiazox Chemical compound S([C@H]([C@@H]1C)C=2C=CC(Cl)=CC=2)C(=O)N1C(=O)NC1CCCCC1 XGWIJUOSCAQSSV-XHDPSFHLSA-N 0.000 description 1
- RMOGWMIKYWRTKW-UONOGXRCSA-N (S,S)-paclobutrazol Chemical compound C([C@@H]([C@@H](O)C(C)(C)C)N1N=CN=C1)C1=CC=C(Cl)C=C1 RMOGWMIKYWRTKW-UONOGXRCSA-N 0.000 description 1
- QNBTYORWCCMPQP-JXAWBTAJSA-N (Z)-dimethomorph Chemical compound C1=C(OC)C(OC)=CC=C1C(\C=1C=CC(Cl)=CC=1)=C/C(=O)N1CCOCC1 QNBTYORWCCMPQP-JXAWBTAJSA-N 0.000 description 1
- PCKNFPQPGUWFHO-SXBRIOAWSA-N (Z)-flucycloxuron Chemical compound FC1=CC=CC(F)=C1C(=O)NC(=O)NC(C=C1)=CC=C1CO\N=C(C=1C=CC(Cl)=CC=1)\C1CC1 PCKNFPQPGUWFHO-SXBRIOAWSA-N 0.000 description 1
- GNPWYHFXSMINJQ-UHFFFAOYSA-N 1,2-dimethyl-3-(1-phenylethyl)benzene Chemical compound C=1C=CC(C)=C(C)C=1C(C)C1=CC=CC=C1 GNPWYHFXSMINJQ-UHFFFAOYSA-N 0.000 description 1
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
- VZXPHDGHQXLXJC-UHFFFAOYSA-N 1,6-diisocyanato-5,6-dimethylheptane Chemical compound O=C=NC(C)(C)C(C)CCCCN=C=O VZXPHDGHQXLXJC-UHFFFAOYSA-N 0.000 description 1
- WURBVZBTWMNKQT-UHFFFAOYSA-N 1-(4-chlorophenoxy)-3,3-dimethyl-1-(1,2,4-triazol-1-yl)butan-2-one Chemical compound C1=NC=NN1C(C(=O)C(C)(C)C)OC1=CC=C(Cl)C=C1 WURBVZBTWMNKQT-UHFFFAOYSA-N 0.000 description 1
- 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 1
- KWUXACZIGUKKOV-UHFFFAOYSA-N 12-acetyloxyoctadecanoic acid Chemical compound CCCCCCC(OC(C)=O)CCCCCCCCCCC(O)=O KWUXACZIGUKKOV-UHFFFAOYSA-N 0.000 description 1
- 229940114069 12-hydroxystearate Drugs 0.000 description 1
- 229940114072 12-hydroxystearic acid Drugs 0.000 description 1
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 description 1
- 239000005631 2,4-Dichlorophenoxyacetic acid Substances 0.000 description 1
- FIOZHYUMQMOMDK-UHFFFAOYSA-N 2,6-difluoro-n-[[2-fluoro-4-(1,1,2,2-tetrafluoroethoxy)phenyl]carbamoyl]benzamide Chemical compound FC1=CC(OC(F)(F)C(F)F)=CC=C1NC(=O)NC(=O)C1=C(F)C=CC=C1F FIOZHYUMQMOMDK-UHFFFAOYSA-N 0.000 description 1
- QFUSCYRJMXLNRB-UHFFFAOYSA-N 2,6-dinitroaniline Chemical class NC1=C([N+]([O-])=O)C=CC=C1[N+]([O-])=O QFUSCYRJMXLNRB-UHFFFAOYSA-N 0.000 description 1
- GDMDOMRUYVLLHM-UHFFFAOYSA-N 2-(1-iodoethyl)pentyl carbamate Chemical compound CCCC(C(C)I)COC(N)=O GDMDOMRUYVLLHM-UHFFFAOYSA-N 0.000 description 1
- WNTGYJSOUMFZEP-UHFFFAOYSA-N 2-(4-chloro-2-methylphenoxy)propanoic acid Chemical compound OC(=O)C(C)OC1=CC=C(Cl)C=C1C WNTGYJSOUMFZEP-UHFFFAOYSA-N 0.000 description 1
- UFNOUKDBUJZYDE-UHFFFAOYSA-N 2-(4-chlorophenyl)-3-cyclopropyl-1-(1H-1,2,4-triazol-1-yl)butan-2-ol Chemical compound C1=NC=NN1CC(O)(C=1C=CC(Cl)=CC=1)C(C)C1CC1 UFNOUKDBUJZYDE-UHFFFAOYSA-N 0.000 description 1
- CLQMBPJKHLGMQK-UHFFFAOYSA-N 2-(4-isopropyl-4-methyl-5-oxo-4,5-dihydro-1H-imidazol-2-yl)nicotinic acid Chemical compound N1C(=O)C(C(C)C)(C)N=C1C1=NC=CC=C1C(O)=O CLQMBPJKHLGMQK-UHFFFAOYSA-N 0.000 description 1
- CABMTIJINOIHOD-UHFFFAOYSA-N 2-[4-methyl-5-oxo-4-(propan-2-yl)-4,5-dihydro-1H-imidazol-2-yl]quinoline-3-carboxylic acid Chemical compound N1C(=O)C(C(C)C)(C)N=C1C1=NC2=CC=CC=C2C=C1C(O)=O CABMTIJINOIHOD-UHFFFAOYSA-N 0.000 description 1
- ZBMRKNMTMPPMMK-UHFFFAOYSA-N 2-amino-4-[hydroxy(methyl)phosphoryl]butanoic acid;azane Chemical class [NH4+].CP(O)(=O)CCC(N)C([O-])=O ZBMRKNMTMPPMMK-UHFFFAOYSA-N 0.000 description 1
- CHZCERSEMVWNHL-UHFFFAOYSA-N 2-hydroxybenzonitrile Chemical class OC1=CC=CC=C1C#N CHZCERSEMVWNHL-UHFFFAOYSA-N 0.000 description 1
- 229940100555 2-methyl-4-isothiazolin-3-one Drugs 0.000 description 1
- UPMXNNIRAGDFEH-UHFFFAOYSA-N 3,5-dibromo-4-hydroxybenzonitrile Chemical compound OC1=C(Br)C=C(C#N)C=C1Br UPMXNNIRAGDFEH-UHFFFAOYSA-N 0.000 description 1
- CAAMSDWKXXPUJR-UHFFFAOYSA-N 3,5-dihydro-4H-imidazol-4-one Chemical class O=C1CNC=N1 CAAMSDWKXXPUJR-UHFFFAOYSA-N 0.000 description 1
- YHCCCMIWRBJYHG-UHFFFAOYSA-N 3-(2-ethylhexoxymethyl)heptane Chemical compound CCCCC(CC)COCC(CC)CCCC YHCCCMIWRBJYHG-UHFFFAOYSA-N 0.000 description 1
- GPUHJQHXIFJPGN-UHFFFAOYSA-N 3-(3,5-dichlorophenyl)-1-(3-methylbutanoyl)imidazolidine-2,4-dione Chemical compound O=C1N(C(=O)CC(C)C)CC(=O)N1C1=CC(Cl)=CC(Cl)=C1 GPUHJQHXIFJPGN-UHFFFAOYSA-N 0.000 description 1
- FSCWZHGZWWDELK-UHFFFAOYSA-N 3-(3,5-dichlorophenyl)-5-ethenyl-5-methyl-2,4-oxazolidinedione Chemical compound O=C1C(C)(C=C)OC(=O)N1C1=CC(Cl)=CC(Cl)=C1 FSCWZHGZWWDELK-UHFFFAOYSA-N 0.000 description 1
- PFEFOHMLVFUELJ-UHFFFAOYSA-N 3-sulfanylideneisoindol-1-one Chemical compound C1=CC=C2C(=O)NC(=S)C2=C1 PFEFOHMLVFUELJ-UHFFFAOYSA-N 0.000 description 1
- NMWKWBPNKPGATC-UHFFFAOYSA-N 4,5,6,7-tetrachloro-2-benzofuran-1(3H)-one Chemical compound ClC1=C(Cl)C(Cl)=C2COC(=O)C2=C1Cl NMWKWBPNKPGATC-UHFFFAOYSA-N 0.000 description 1
- GICUQIXVWFUPOQ-UHFFFAOYSA-N 4-chloro-2-(2-chloro-2-methylpropyl)-5-[(6-iodopyridin-3-yl)methoxy]pyridazin-3-one Chemical compound O=C1N(CC(C)(Cl)C)N=CC(OCC=2C=NC(I)=CC=2)=C1Cl GICUQIXVWFUPOQ-UHFFFAOYSA-N 0.000 description 1
- QCPASDYEQAVIJF-UHFFFAOYSA-N 4-chloro-3-methyl-1,3-benzothiazol-2-one Chemical compound C1=CC=C2SC(=O)N(C)C2=C1Cl QCPASDYEQAVIJF-UHFFFAOYSA-N 0.000 description 1
- 150000005168 4-hydroxybenzoic acids Chemical class 0.000 description 1
- XJFIKRXIJXAJGH-UHFFFAOYSA-N 5-chloro-1,3-dihydroimidazo[4,5-b]pyridin-2-one Chemical group ClC1=CC=C2NC(=O)NC2=N1 XJFIKRXIJXAJGH-UHFFFAOYSA-N 0.000 description 1
- NRTLIYOWLVMQBO-UHFFFAOYSA-N 5-chloro-1,3-dimethyl-N-(1,1,3-trimethyl-1,3-dihydro-2-benzofuran-4-yl)pyrazole-4-carboxamide Chemical compound C=12C(C)OC(C)(C)C2=CC=CC=1NC(=O)C=1C(C)=NN(C)C=1Cl NRTLIYOWLVMQBO-UHFFFAOYSA-N 0.000 description 1
- 229940100484 5-chloro-2-methyl-4-isothiazolin-3-one Drugs 0.000 description 1
- PCCSBWNGDMYFCW-UHFFFAOYSA-N 5-methyl-5-(4-phenoxyphenyl)-3-(phenylamino)-1,3-oxazolidine-2,4-dione Chemical compound O=C1C(C)(C=2C=CC(OC=3C=CC=CC=3)=CC=2)OC(=O)N1NC1=CC=CC=C1 PCCSBWNGDMYFCW-UHFFFAOYSA-N 0.000 description 1
- IBSREHMXUMOFBB-JFUDTMANSA-N 5u8924t11h Chemical compound O1[C@@H](C)[C@H](O)[C@@H](OC)C[C@@H]1O[C@@H]1[C@@H](OC)C[C@H](O[C@@H]2C(=C/C[C@@H]3C[C@@H](C[C@@]4(O3)C=C[C@H](C)[C@@H](C(C)C)O4)OC(=O)[C@@H]3C=C(C)[C@@H](O)[C@H]4OC\C([C@@]34O)=C/C=C/[C@@H]2C)/C)O[C@H]1C.C1=C[C@H](C)[C@@H]([C@@H](C)CC)O[C@]11O[C@H](C\C=C(C)\[C@@H](O[C@@H]2O[C@@H](C)[C@H](O[C@@H]3O[C@@H](C)[C@H](O)[C@@H](OC)C3)[C@@H](OC)C2)[C@@H](C)\C=C\C=C/2[C@]3([C@H](C(=O)O4)C=C(C)[C@@H](O)[C@H]3OC\2)O)C[C@H]4C1 IBSREHMXUMOFBB-JFUDTMANSA-N 0.000 description 1
- 239000005660 Abamectin Substances 0.000 description 1
- 239000005875 Acetamiprid Substances 0.000 description 1
- 239000005472 Bensulfuron methyl Substances 0.000 description 1
- 239000005476 Bentazone Substances 0.000 description 1
- 239000005489 Bromoxynil Substances 0.000 description 1
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- RGNPBRKPHBKNKX-UHFFFAOYSA-N hexaflumuron Chemical compound C1=C(Cl)C(OC(F)(F)C(F)F)=C(Cl)C=C1NC(=O)NC(=O)C1=C(F)C=CC=C1F RGNPBRKPHBKNKX-UHFFFAOYSA-N 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 229940056881 imidacloprid Drugs 0.000 description 1
- YWTYJOPNNQFBPC-UHFFFAOYSA-N imidacloprid Chemical compound [O-][N+](=O)\N=C1/NCCN1CC1=CC=C(Cl)N=C1 YWTYJOPNNQFBPC-UHFFFAOYSA-N 0.000 description 1
- VBCVPMMZEGZULK-NRFANRHFSA-N indoxacarb Chemical compound C([C@@]1(OC2)C(=O)OC)C3=CC(Cl)=CC=C3C1=NN2C(=O)N(C(=O)OC)C1=CC=C(OC(F)(F)F)C=C1 VBCVPMMZEGZULK-NRFANRHFSA-N 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- NRXQIUSYPAHGNM-UHFFFAOYSA-N ioxynil Chemical compound OC1=C(I)C=C(C#N)C=C1I NRXQIUSYPAHGNM-UHFFFAOYSA-N 0.000 description 1
- ONUFESLQCSAYKA-UHFFFAOYSA-N iprodione Chemical compound O=C1N(C(=O)NC(C)C)CC(=O)N1C1=CC(Cl)=CC(Cl)=C1 ONUFESLQCSAYKA-UHFFFAOYSA-N 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 1
- QBSJMKIUCUGGNG-UHFFFAOYSA-N isoprocarb Chemical compound CNC(=O)OC1=CC=CC=C1C(C)C QBSJMKIUCUGGNG-UHFFFAOYSA-N 0.000 description 1
- PUIYMUZLKQOUOZ-UHFFFAOYSA-N isoproturon Chemical compound CC(C)C1=CC=C(NC(=O)N(C)C)C=C1 PUIYMUZLKQOUOZ-UHFFFAOYSA-N 0.000 description 1
- OYIKARCXOQLFHF-UHFFFAOYSA-N isoxaflutole Chemical compound CS(=O)(=O)C1=CC(C(F)(F)F)=CC=C1C(=O)C1=C(C2CC2)ON=C1 OYIKARCXOQLFHF-UHFFFAOYSA-N 0.000 description 1
- 229940088649 isoxaflutole Drugs 0.000 description 1
- 235000010420 locust bean gum Nutrition 0.000 description 1
- 239000000711 locust bean gum Substances 0.000 description 1
- 229960000521 lufenuron Drugs 0.000 description 1
- PWPJGUXAGUPAHP-UHFFFAOYSA-N lufenuron Chemical compound C1=C(Cl)C(OC(F)(F)C(C(F)(F)F)F)=CC(Cl)=C1NC(=O)NC(=O)C1=C(F)C=CC=C1F PWPJGUXAGUPAHP-UHFFFAOYSA-N 0.000 description 1
- XIGAUIHYSDTJHW-UHFFFAOYSA-N mefenacet Chemical compound N=1C2=CC=CC=C2SC=1OCC(=O)N(C)C1=CC=CC=C1 XIGAUIHYSDTJHW-UHFFFAOYSA-N 0.000 description 1
- CIFWZNRJIBNXRE-UHFFFAOYSA-N mepanipyrim Chemical compound CC#CC1=CC(C)=NC(NC=2C=CC=CC=2)=N1 CIFWZNRJIBNXRE-UHFFFAOYSA-N 0.000 description 1
- BCTQJXQXJVLSIG-UHFFFAOYSA-N mepronil Chemical compound CC(C)OC1=CC=CC(NC(=O)C=2C(=CC=CC=2)C)=C1 BCTQJXQXJVLSIG-UHFFFAOYSA-N 0.000 description 1
- NNKVPIKMPCQWCG-UHFFFAOYSA-N methamidophos Chemical compound COP(N)(=O)SC NNKVPIKMPCQWCG-UHFFFAOYSA-N 0.000 description 1
- MEBQXILRKZHVCX-UHFFFAOYSA-N methidathion Chemical compound COC1=NN(CSP(=S)(OC)OC)C(=O)S1 MEBQXILRKZHVCX-UHFFFAOYSA-N 0.000 description 1
- UHXUZOCRWCRNSJ-QPJJXVBHSA-N methomyl Chemical compound CNC(=O)O\N=C(/C)SC UHXUZOCRWCRNSJ-QPJJXVBHSA-N 0.000 description 1
- ZTYVMAQSHCZXLF-UHFFFAOYSA-N methyl 2-[[4,6-bis(difluoromethoxy)pyrimidin-2-yl]carbamoylsulfamoyl]benzoate Chemical group COC(=O)C1=CC=CC=C1S(=O)(=O)NC(=O)NC1=NC(OC(F)F)=CC(OC(F)F)=N1 ZTYVMAQSHCZXLF-UHFFFAOYSA-N 0.000 description 1
- ZQEIXNIJLIKNTD-UHFFFAOYSA-N methyl N-(2,6-dimethylphenyl)-N-(methoxyacetyl)alaninate Chemical compound COCC(=O)N(C(C)C(=O)OC)C1=C(C)C=CC=C1C ZQEIXNIJLIKNTD-UHFFFAOYSA-N 0.000 description 1
- BEGLCMHJXHIJLR-UHFFFAOYSA-N methylisothiazolinone Chemical compound CN1SC=CC1=O BEGLCMHJXHIJLR-UHFFFAOYSA-N 0.000 description 1
- VOEYXMAFNDNNED-UHFFFAOYSA-N metolcarb Chemical compound CNC(=O)OC1=CC=CC(C)=C1 VOEYXMAFNDNNED-UHFFFAOYSA-N 0.000 description 1
- FOXFZRUHNHCZPX-UHFFFAOYSA-N metribuzin Chemical compound CSC1=NN=C(C(C)(C)C)C(=O)N1N FOXFZRUHNHCZPX-UHFFFAOYSA-N 0.000 description 1
- 229960001952 metrifonate Drugs 0.000 description 1
- RSMUVYRMZCOLBH-UHFFFAOYSA-N metsulfuron methyl Chemical group COC(=O)C1=CC=CC=C1S(=O)(=O)NC(=O)NC1=NC(C)=NC(OC)=N1 RSMUVYRMZCOLBH-UHFFFAOYSA-N 0.000 description 1
- ZLBGSRMUSVULIE-GSMJGMFJSA-N milbemycin A3 Chemical compound O1[C@H](C)[C@@H](C)CC[C@@]11O[C@H](C\C=C(C)\C[C@@H](C)\C=C\C=C/2[C@]3([C@H](C(=O)O4)C=C(C)[C@@H](O)[C@H]3OC\2)O)C[C@H]4C1 ZLBGSRMUSVULIE-GSMJGMFJSA-N 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- RTCOGUMHFFWOJV-UHFFFAOYSA-N nicosulfuron Chemical compound COC1=CC(OC)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CN=2)C(=O)N(C)C)=N1 RTCOGUMHFFWOJV-UHFFFAOYSA-N 0.000 description 1
- 229940079888 nitenpyram Drugs 0.000 description 1
- NVGOPFQZYCNLDU-UHFFFAOYSA-N norflurazon Chemical compound O=C1C(Cl)=C(NC)C=NN1C1=CC=CC(C(F)(F)F)=C1 NVGOPFQZYCNLDU-UHFFFAOYSA-N 0.000 description 1
- NJPPVKZQTLUDBO-UHFFFAOYSA-N novaluron Chemical compound C1=C(Cl)C(OC(F)(F)C(OC(F)(F)F)F)=CC=C1NC(=O)NC(=O)C1=C(F)C=CC=C1F NJPPVKZQTLUDBO-UHFFFAOYSA-N 0.000 description 1
- 229960000321 oxolinic acid Drugs 0.000 description 1
- FIKAKWIAUPDISJ-UHFFFAOYSA-L paraquat dichloride Chemical compound [Cl-].[Cl-].C1=C[N+](C)=CC=C1C1=CC=[N+](C)C=C1 FIKAKWIAUPDISJ-UHFFFAOYSA-L 0.000 description 1
- CHIFOSRWCNZCFN-UHFFFAOYSA-N pendimethalin Chemical compound CCC(CC)NC1=C([N+]([O-])=O)C=C(C)C(C)=C1[N+]([O-])=O CHIFOSRWCNZCFN-UHFFFAOYSA-N 0.000 description 1
- XAMUDJHXFNRLCY-UHFFFAOYSA-N phenthoate Chemical compound CCOC(=O)C(SP(=S)(OC)OC)C1=CC=CC=C1 XAMUDJHXFNRLCY-UHFFFAOYSA-N 0.000 description 1
- PWXJULSLLONQHY-UHFFFAOYSA-N phenylcarbamic acid Chemical class OC(=O)NC1=CC=CC=C1 PWXJULSLLONQHY-UHFFFAOYSA-N 0.000 description 1
- IOUNQDKNJZEDEP-UHFFFAOYSA-N phosalone Chemical compound C1=C(Cl)C=C2OC(=O)N(CSP(=S)(OCC)OCC)C2=C1 IOUNQDKNJZEDEP-UHFFFAOYSA-N 0.000 description 1
- YFGYUFNIOHWBOB-UHFFFAOYSA-N pirimicarb Chemical compound CN(C)C(=O)OC1=NC(N(C)C)=NC(C)=C1C YFGYUFNIOHWBOB-UHFFFAOYSA-N 0.000 description 1
- 229920001495 poly(sodium acrylate) polymer Polymers 0.000 description 1
- 229920001282 polysaccharide Polymers 0.000 description 1
- 239000005017 polysaccharide Substances 0.000 description 1
- 229920005749 polyurethane resin Polymers 0.000 description 1
- WHHIPMZEDGBUCC-UHFFFAOYSA-N probenazole Chemical compound C1=CC=C2C(OCC=C)=NS(=O)(=O)C2=C1 WHHIPMZEDGBUCC-UHFFFAOYSA-N 0.000 description 1
- QXJKBPAVAHBARF-BETUJISGSA-N procymidone Chemical compound O=C([C@]1(C)C[C@@]1(C1=O)C)N1C1=CC(Cl)=CC(Cl)=C1 QXJKBPAVAHBARF-BETUJISGSA-N 0.000 description 1
- LFULEKSKNZEWOE-UHFFFAOYSA-N propanil Chemical compound CCC(=O)NC1=CC=C(Cl)C(Cl)=C1 LFULEKSKNZEWOE-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- QHMTXANCGGJZRX-WUXMJOGZSA-N pymetrozine Chemical compound C1C(C)=NNC(=O)N1\N=C\C1=CC=CN=C1 QHMTXANCGGJZRX-WUXMJOGZSA-N 0.000 description 1
- JOOMJVFZQRQWKR-UHFFFAOYSA-N pyrazophos Chemical compound N1=C(C)C(C(=O)OCC)=CN2N=C(OP(=S)(OCC)OCC)C=C21 JOOMJVFZQRQWKR-UHFFFAOYSA-N 0.000 description 1
- DWFZBUWUXWZWKD-UHFFFAOYSA-N pyridaben Chemical compound C1=CC(C(C)(C)C)=CC=C1CSC1=C(Cl)C(=O)N(C(C)(C)C)N=C1 DWFZBUWUXWZWKD-UHFFFAOYSA-N 0.000 description 1
- CXJSOEPQXUCJSA-UHFFFAOYSA-N pyridaphenthion Chemical compound N1=C(OP(=S)(OCC)OCC)C=CC(=O)N1C1=CC=CC=C1 CXJSOEPQXUCJSA-UHFFFAOYSA-N 0.000 description 1
- ZLIBICFPKPWGIZ-UHFFFAOYSA-N pyrimethanil Chemical compound CC1=CC(C)=NC(NC=2C=CC=CC=2)=N1 ZLIBICFPKPWGIZ-UHFFFAOYSA-N 0.000 description 1
- ITKAIUGKVKDENI-UHFFFAOYSA-N pyrimidifen Chemical compound CC1=C(C)C(CCOCC)=CC=C1OCCNC1=NC=NC(CC)=C1Cl ITKAIUGKVKDENI-UHFFFAOYSA-N 0.000 description 1
- NHDHVHZZCFYRSB-UHFFFAOYSA-N pyriproxyfen Chemical compound C=1C=CC=NC=1OC(C)COC(C=C1)=CC=C1OC1=CC=CC=C1 NHDHVHZZCFYRSB-UHFFFAOYSA-N 0.000 description 1
- XRJLAOUDSILTFT-UHFFFAOYSA-N pyroquilon Chemical compound O=C1CCC2=CC=CC3=C2N1CC3 XRJLAOUDSILTFT-UHFFFAOYSA-N 0.000 description 1
- JYQUHIFYBATCCY-UHFFFAOYSA-N quinalphos Chemical compound C1=CC=CC2=NC(OP(=S)(OCC)OCC)=CN=C21 JYQUHIFYBATCCY-UHFFFAOYSA-N 0.000 description 1
- WBHHMMIMDMUBKC-XLNAKTSKSA-N ricinelaidic acid Chemical compound CCCCCC[C@@H](O)C\C=C\CCCCCCCC(O)=O WBHHMMIMDMUBKC-XLNAKTSKSA-N 0.000 description 1
- WBHHMMIMDMUBKC-QJWNTBNXSA-M ricinoleate Chemical compound CCCCCC[C@@H](O)C\C=C/CCCCCCCC([O-])=O WBHHMMIMDMUBKC-QJWNTBNXSA-M 0.000 description 1
- 229940066675 ricinoleate Drugs 0.000 description 1
- 229960003656 ricinoleic acid Drugs 0.000 description 1
- FEUQNCSVHBHROZ-UHFFFAOYSA-N ricinoleic acid Natural products CCCCCCC(O[Si](C)(C)C)CC=CCCCCCCCC(=O)OC FEUQNCSVHBHROZ-UHFFFAOYSA-N 0.000 description 1
- 229940058287 salicylic acid derivative anticestodals Drugs 0.000 description 1
- 150000003872 salicylic acid derivatives Chemical class 0.000 description 1
- 229910021647 smectite Inorganic materials 0.000 description 1
- NNMHYFLPFNGQFZ-UHFFFAOYSA-M sodium polyacrylate Chemical compound [Na+].[O-]C(=O)C=C NNMHYFLPFNGQFZ-UHFFFAOYSA-M 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 238000001694 spray drying Methods 0.000 description 1
- OORLZFUTLGXMEF-UHFFFAOYSA-N sulfentrazone Chemical compound O=C1N(C(F)F)C(C)=NN1C1=CC(NS(C)(=O)=O)=C(Cl)C=C1Cl OORLZFUTLGXMEF-UHFFFAOYSA-N 0.000 description 1
- YROXIXLRRCOBKF-UHFFFAOYSA-N sulfonylurea Chemical class OC(=N)N=S(=O)=O YROXIXLRRCOBKF-UHFFFAOYSA-N 0.000 description 1
- QYPNKSZPJQQLRK-UHFFFAOYSA-N tebufenozide Chemical compound C1=CC(CC)=CC=C1C(=O)NN(C(C)(C)C)C(=O)C1=CC(C)=CC(C)=C1 QYPNKSZPJQQLRK-UHFFFAOYSA-N 0.000 description 1
- ZZYSLNWGKKDOML-UHFFFAOYSA-N tebufenpyrad Chemical compound CCC1=NN(C)C(C(=O)NCC=2C=CC(=CC=2)C(C)(C)C)=C1Cl ZZYSLNWGKKDOML-UHFFFAOYSA-N 0.000 description 1
- CJDWRQLODFKPEL-UHFFFAOYSA-N teflubenzuron Chemical compound FC1=CC=CC(F)=C1C(=O)NC(=O)NC1=CC(Cl)=C(F)C(Cl)=C1F CJDWRQLODFKPEL-UHFFFAOYSA-N 0.000 description 1
- UBCKGWBNUIFUST-YHYXMXQVSA-N tetrachlorvinphos Chemical compound COP(=O)(OC)O\C(=C/Cl)C1=CC(Cl)=C(Cl)C=C1Cl UBCKGWBNUIFUST-YHYXMXQVSA-N 0.000 description 1
- 239000004308 thiabendazole Substances 0.000 description 1
- WJCNZQLZVWNLKY-UHFFFAOYSA-N thiabendazole Chemical compound S1C=NC(C=2NC3=CC=CC=C3N=2)=C1 WJCNZQLZVWNLKY-UHFFFAOYSA-N 0.000 description 1
- 229960004546 thiabendazole Drugs 0.000 description 1
- 235000010296 thiabendazole Nutrition 0.000 description 1
- NWWZPOKUUAIXIW-FLIBITNWSA-N thiamethoxam Chemical compound [O-][N+](=O)\N=C/1N(C)COCN\1CC1=CN=C(Cl)S1 NWWZPOKUUAIXIW-FLIBITNWSA-N 0.000 description 1
- DNVLJEWNNDHELH-UHFFFAOYSA-N thiocyclam Chemical compound CN(C)C1CSSSC1 DNVLJEWNNDHELH-UHFFFAOYSA-N 0.000 description 1
- BAKXBZPQTXCKRR-UHFFFAOYSA-N thiodicarb Chemical compound CSC(C)=NOC(=O)NSNC(=O)ON=C(C)SC BAKXBZPQTXCKRR-UHFFFAOYSA-N 0.000 description 1
- QGHREAKMXXNCOA-UHFFFAOYSA-N thiophanate-methyl Chemical compound COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC QGHREAKMXXNCOA-UHFFFAOYSA-N 0.000 description 1
- OBZIQQJJIKNWNO-UHFFFAOYSA-N tolclofos-methyl Chemical compound COP(=S)(OC)OC1=C(Cl)C=C(C)C=C1Cl OBZIQQJJIKNWNO-UHFFFAOYSA-N 0.000 description 1
- NKNFWVNSBIXGLL-UHFFFAOYSA-N triazamate Chemical compound CCOC(=O)CSC1=NC(C(C)(C)C)=NN1C(=O)N(C)C NKNFWVNSBIXGLL-UHFFFAOYSA-N 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- NFACJZMKEDPNKN-UHFFFAOYSA-N trichlorfon Chemical compound COP(=O)(OC)C(O)C(Cl)(Cl)Cl NFACJZMKEDPNKN-UHFFFAOYSA-N 0.000 description 1
- DQJCHOQLCLEDLL-UHFFFAOYSA-N tricyclazole Chemical compound CC1=CC=CC2=C1N1C=NN=C1S2 DQJCHOQLCLEDLL-UHFFFAOYSA-N 0.000 description 1
- XAIPTRIXGHTTNT-UHFFFAOYSA-N triflumuron Chemical compound C1=CC(OC(F)(F)F)=CC=C1NC(=O)NC(=O)C1=CC=CC=C1Cl XAIPTRIXGHTTNT-UHFFFAOYSA-N 0.000 description 1
- ZSDSQXJSNMTJDA-UHFFFAOYSA-N trifluralin Chemical compound CCCN(CCC)C1=C([N+]([O-])=O)C=C(C(F)(F)F)C=C1[N+]([O-])=O ZSDSQXJSNMTJDA-UHFFFAOYSA-N 0.000 description 1
- IMEVJVISCHQJRM-UHFFFAOYSA-N triflusulfuron-methyl Chemical group COC(=O)C1=CC=CC(C)=C1S(=O)(=O)NC(=O)NC1=NC(OCC(F)(F)F)=NC(N(C)C)=N1 IMEVJVISCHQJRM-UHFFFAOYSA-N 0.000 description 1
- FLTJDUOFAQWHDF-UHFFFAOYSA-N trimethyl pentane Natural products CCCCC(C)(C)C FLTJDUOFAQWHDF-UHFFFAOYSA-N 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- LESVOLZBIFDZGS-UHFFFAOYSA-N vamidothion Chemical compound CNC(=O)C(C)SCCSP(=O)(OC)OC LESVOLZBIFDZGS-UHFFFAOYSA-N 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 238000001238 wet grinding Methods 0.000 description 1
- WCJYTPVNMWIZCG-UHFFFAOYSA-N xylylcarb Chemical compound CNC(=O)OC1=CC=C(C)C(C)=C1 WCJYTPVNMWIZCG-UHFFFAOYSA-N 0.000 description 1
- UHVMMEOXYDMDKI-JKYCWFKZSA-L zinc;1-(5-cyanopyridin-2-yl)-3-[(1s,2s)-2-(6-fluoro-2-hydroxy-3-propanoylphenyl)cyclopropyl]urea;diacetate Chemical compound [Zn+2].CC([O-])=O.CC([O-])=O.CCC(=O)C1=CC=C(F)C([C@H]2[C@H](C2)NC(=O)NC=2N=CC(=CC=2)C#N)=C1O UHVMMEOXYDMDKI-JKYCWFKZSA-L 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
- A01N25/26—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
-
- 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
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J13/00—Colloid chemistry, e.g. the production of colloidal materials or their solutions, not otherwise provided for; Making microcapsules or microballoons
- B01J13/02—Making microcapsules or microballoons
- B01J13/06—Making microcapsules or microballoons by phase separation
- B01J13/14—Polymerisation; cross-linking
- B01J13/16—Interfacial polymerisation
Definitions
- the present invention relates to a method for producing a microcapsule and a microcapsule produced by the method.
- a microcapsule formulation of a pesticidal compound is a formulation which is intended to control the release timing of the pesticidal compound contained therein.
- An object of the present invention is to provide a technique for delaying the release timing of the pesticidal compound with a microcapsule containing a pesticidal compound in a fatty acid ester such as methyl 0- acetylricinoleate .
- the inventors of the present invention have found that the timing of release of the pesticidal compound from the microcapsule is delayed when a microcapsule is produced by using a mixture of a pesticidal compound, a fatty acid ester such as methyl O-acetylricinoleate and a polyisocyanate being kept at 20 to 60°C for 3 hours or more.
- the inventors have also found that the microcapsule produced by the production method is excellent in light stability as compared to a conventional microcapsule.
- a method for producing a microcapsule which comprises:
- R 1 represents a C1-C4 alkyl group
- R 2 represents a C1-C4 alkyl group
- a microcapsule from which release of a pesticidal compound is more controlled than that from a conventional microcapsule can be obtained.
- the method for producing a microcapsule of the present invention comprises the following steps: step (1) keeping a mixture of a pesticidal compound, a compound represented by formula (I) and a polyisocyanate at 20 to 60°C for 3 hours or more:
- step (2) then adding the mixture into water containing a polyol or a polyamine, and producing liquid droplets in the water; and step (3) forming a film of polyurethane or polyurea around the droplets.
- the pesticidal compound is preferably a solid pesticidal compound.
- the solid pesticidal compound usually means a compound having pesticidal activity and having a melting point of 15°C or higher, preferably 50 0 C or higher. More preferably, the solid pesticidal compound as used herein is a compound having pesticidal activity whose melting point is 15°C or higher, preferably 50 0 C or higher and whose solubility is 5% by weight or less in the compound represented by the above formula (I).
- the pesticidal compound used in the present invention include an insecticidal compound, a fungicidal compound, a herbicidal compound, an insect growth regulating compound, a plant growth regulating compound, and an insect repelling compound.
- insecticidal compound examples include carbamate compounds such as propoxur, isoprocarb, xylylcarb, metolcarb, XMC, carbaryl, pirimicarb, carbofuran, methomyl, fenoxycarb, alanycarb, and metoxadiazone; organophosphorus compounds such as acephate, phenthoate, vamidothion, trichlorfon, monocrotophos, tetrachlorvinphos, dimethylvinphos, phosalone, chlorpyrifos, chlorpyrifos- methyl, pyridaphenthion, quinalphos, methidathion, methamidophos, dimethoate, formothion, azinphos-ethyl, azinphos-methyl, and salithion; neonicotinoid compounds such as imidacloprid, nitenpyram, acetamiprid, clothiani
- fungicidal compound examples include benzimidazole compounds such as benomyl, carbendazim, thiabendazole, and thiophanate-methyl; phenylcarbamate compounds such as diethofencarb; dicarboxyimide compounds such as procymidone, iprodione, and vinclozolin; azole compounds such as diniconazole, propenazole, epoxyconazole, tebuconazole, difenoconazole, cyproconazole, flusilazole, and triadimefon; acylalanine compounds such as metalaxyl; carboxyamide compounds such as furametpyr, mepronil, flutolanil, and trifluzamide; organophosphorus compounds such as tolclofos-methyl, fosetyl-aluminum, and pyrazophos; anilinopyrimidine compounds such as pyrimethanil, mepanipyrim, and cyprodinil;
- herbicidal compound examples include triazine compounds such as atrazine, and metribuzin; urea compounds such as fluometuron, and isoproturon; hydroxybenzonitrile compounds such as bromoxynil, and ioxynil; 2,6- dinitroaniline compounds such as pendimethalin, and trifluralin; aryloxyalkanoic acid compounds and salts thereof such as 2,4-D, dicamba, fluroxypyr, and mecoprop; sulfonylurea compounds such as bensulfuron-methyl, metsulfuron-methyl, nicosulfuron, primisulfuron-methyl, and cyclosulfamuron; imidazolinone compounds and salts thereof such as imazapyr, imazaquin, and imazethapyr; sulfentrazone, paraquat, flumetsulam, triflusulfuron-methyl, fenoxaprop-p- ethyl, cyhalof
- insect growth regulating compound examples include benzoylurea compounds such as diflubenzuron, chlorfluazuron, lufenuron, hexaflumuron, flufenoxuron, flucycloxuron, cyromazine, diafenthiuron, hexythiazox, novaluron, teflubenzuron, triflumuron, l-(2,6- difluorobenzoyl) -3-[2-fluoro-4- (trifluoromethyl) phenyl] urea, l-(2, 6-difluorobenzoyl) -3- [2-fluoro-4- (1,1,2,3,3,3- hexafluoropropoxy) phenyl] urea, and 1- (2 , 6-difluorobenzoyl) - 3-[2-fluoro-4- (1,1,2, 2-tetrafluoroethoxy) phenyl] urea; and pyriproxyfen.
- Examples of the plant growth regulating compound include maleic hydrazide, chlormequat, ethephon, gibberellin, mepichat chloride, thidiazuron, inabenfide, paclobutrazol, and uniconazole.
- Examples of the insect repelling compound include IS, 3R, 4R, 6R-carane-3, 4-diol, and dipropyl 2,5- pyridinedicarboxylate .
- Examples of the C1-C4 alkyl groups represented by R 1 or R 2 in formula (I), as used herein, include a methyl group, an ethyl group, a propyl group and a butyl group.
- the compound represented by formula (I) can be obtained by converting the carboxyl group of ricinoleic acid or 12-hydroxystearic acid into an alkoxycarbonyl group by condensation with a lower alcohol compound, and further converting the hydroxyl group of ricinoleate or 12- hydroxystearate into an acyloxy group by condensation with a lower fatty acid.
- Examples of the compound represented by formula (I) include C1-C4 alkyl esters of O-acetylricinoleic acid and C1-C4 alkyl esters of 12-acetoxystearic acid.
- polyisocyanate used in the present invention examples include hexamethylene diisocyanate, an adduct of hexamethylene diisocyanate and trimethylolpropane, a biuret condensate of 3 molecules of hexamethylene diisocyanate, an adduct of tolylene diisocyanate and trimethylolpropane, an isocyanurate condensate of tolylene diisocyanate, an isocyanurate condensate of hexamethylene diisocyanate, an isocyanurate condensate of isophorone diisocyanate, an isocyanate prepolymer in which one isocyanate part of hexamethylene diisocyanate forms an isocyanurate component together with 2 molecules of tolylene diisocyanate and the other isocyanate part forms an isocyanurate component together with 2 molecules of other hexamethylene diisocyanate, 4 , 4' -methylene bis (cyclo
- the weight ratio of the pesticidal compound to the compound represented by formula (I), that is, the weight ratio of the pesticidal compound to the compound represented by formula (I) is usually from 10:100 to 100:100, preferably from 20:100 to 40:100.
- the amount of the polyisocyanate used in the present invention is usually determined depending on the amount of the film of a microcapsule to be produced.
- the amount of the film of a microcapsule to be produced is usually from 5 to 45% by weight, preferably from 10 to 30% by weight of the weight of the entire microcapsule.
- the amount of the polyisocyanate used in the present invention is usually from 25 to 90% by weight, preferably from 40 to 70% by weight of the weight of the film of a microcapsule.
- the pesticidal compound is usually dissolved or suspended in the compound represented by formula (I).
- the mixture of a pesticidal compound, a compound represented by formula (I) and a polyisocyanate used in the step (1) can be prepared by mixing the pesticidal compound, the compound represented by formula (I) and the polyisocyanate.
- the pesticidal compound is a solid pesticidal compound
- the solid pesticidal compound suspension in the compound represented by formula (I) may be formed in accordance with the solubility of the solid pesticidal compound in the compound represented by formula (I) and the weight ratio of the solid pesticidal compound to the compound represented by formula (I) .
- the mixture of a pesticidal compound, a compound represented by formula (I) and a polyisocyanate used in the step (1) can be prepared, for example, by grinding the solid pesticidal compound in the compound represented by formula (I) to obtain a suspension and then adding the polyisocyanate into the resultant suspension.
- An example of a method for grinding the solid pesticidal compound in the compound represented by formula (I) is a wet grinding method which comprises adding the solid pesticidal compound and, if necessary, beads or the like for grinding to the compound represented by formula (I) and then grinding the mixture with a grinder.
- the grinder examples include mills such as a bead mill, a ball mill and a rod mill, and rotor-stator homogenizers .
- Specific examples of the mill include Attritor (manufactured by MITSUI MIIKE MACHINERY CO., LTD.), Dyno Mill (manufactured by WILLY A. BACHOFEN AG.
- MASCHINENFABRIK MASCHINENFABRIK
- Colloid Mill manufactured by PRIMIX CORP.
- Pearl Mill manufactured by ASHIZAWA FINETECH, LTD.
- Specific examples of the rotor-stator homogenizer include Polytron Homogenizer (manufactured by KINEMATICA AG) .
- Grinding of the solid pesticidal compound in the compound represented by formula (I) may be attained by 2 or more operations.
- the solid pesticidal compound may be coarsely ground in the first operation and then finely ground in the second operation.
- An example of a method for grinding the solid pesticidal compound in the compound represented by formula (I) in 2 operations is a method which comprises using a rotor-stator homogenizer for the first operation and using a mill for the second operation.
- the particle size of the solid pesticidal compound suspended in the compound represented by formula (I) is usually 10 ⁇ m or less, preferably in the range of 1 to 5 ⁇ m in terms of volume median diameter. It is preferred that, based on the gross volume of the particles of the solid pesticidal compound suspended in the compound represented by formula (I), the net volume of particles with a diameter of 10 ⁇ m or more is 10% or less.
- the mixture of a pesticidal compound, a compound represented by formula (I) and a polyisocyanate may further contain an organic solvent.
- the organic solvent include aliphatic hydrocarbons such as trimethylpentane, aromatic hydrocarbons such as phenylxylylethane, alkylbenzene and alkylnaphthalene, ethers such as 2-ethylhexyl ether, and vegetable oils such as cotton seed oil.
- the weight ratio of the organic solvent based on the weight of the compound represented by formula (I) is usually 1/2 or less, preferably 3/7 or less, more preferably 1/4 or less.
- the mixture of a pesticidal compound, a compound represented by formula (I) and a polyisocyanate thus obtained is kept at 20 to 60 0 C for 3 hours or more, preferably at 20 to 40 0 C for 5 hours or more While the mixture of a pesticidal compound, a compound represented by formula (I) and a polyisocyanate is kept at 20 to 60 0 C, the mixture may be stirred or allowed to stand.
- the mixture is usually controlled so as to be kept at 20 to 60 0 C.
- the mixture obtained in the step (1) is added to water containing a polyol or a polyamine, and liquid droplets are produced in the water.
- the water containing a polyol can be prepared, for example, by mixing water and a polyol.
- the water containing a polyamine can be prepared, for example, by mixing water and a polyamine or a polyamine salt.
- Examples of the polyol as used herein include ethylene glycol, propylene glycol, butylene glycol, and cyclopropylene glycol .
- Examples of the polyamine as used herein include ethylenediamine, hexamethylenediamine, diethyltriamine, and triethylenetetramine .
- the amount of the polyol or polyamine used in the present invention is usually determined depending on the amount of the film of a microcapsule to be produced.
- the amount of the polyol used in the present invention is usually from 5 to 80% by weight, preferably from 20 to 60% by weight of the amount of the film of a microcapsule.
- the amount of the polyamine used in the present invention is usually from 5 to 80% by weight, preferably from 20 to 60% by weight of the amount of the film of a microcapsule.
- the weight ratio of water used in the step (2) is usually in a range from 0.8 to 2 times the weight of the mixture obtained in the step (1) .
- deionized water is preferably used.
- Water used in the step (2) may contain a thickening agent, if necessary.
- thickening agent examples include natural polysaccharides such as xanthan gum, rhamsan gum, locust bean gum, carrageenan, welan gum and gum arabic; synthetic polymers such as sodium polyacrylate; semi-synthetic polymers such as carboxymethyl cellulose; mineral powders such as aluminum magnesium silicate, smectite, bentonite, hectorite and fumed silica; and alumina sol.
- An example of a method for preparing liquid droplets in water in the step (2) is a method which comprises adding the mixture obtained in the step (1) to water containing a polyol or a polyamine and then stirring the resultant mixture with a stirrer.
- the stirrer used in this operation include a propeller stirrer, a turbine stirrer and a high-speed shear stirrer. Specific examples of the stirrer include T. K. Homo Mixer, T. K. Homomic Line flow, T. K. Pipeline Homo Mixer, and T. K.
- the particle size of microcapsules finally produced by the method of the present invention is almost identical to that of the liquid droplets prepared in the step (2) .
- the liquid droplets prepared in the step (2) and the microcapsules finally produced by the method of the present invention have a particle diameter of usually in the range of 1 to 80 ⁇ m, preferably 5 to 50 ⁇ m in terms of volume median diameter.
- the liquid droplets existing in water obtained in the step (2) are made of a solution of a polyisocyanate in a compound represented by formula (I).
- the polyisocyanate contained in the liquid droplets is polymerized with the polyol or polyamine existing in the water at the interfaces between the liquid droplets and the water.
- a polyurethane or polyurea film is formed around the liquid droplets to give an aqueous suspension of microcapsules.
- the film of polyurethane resin is formed around the liquid droplets, for example, by heating a water dispersion of the liquid droplets prepared in the step (2) to 40 to 80 0 C and then keeping the dispersion at the same temperature for about 0.5 to 48 hours while stirring.
- the film of polyurea resin is formed around the liquid droplets, for example, by adjusting a water dispersion of the liquid droplets prepared in the step (2) to a neutral to weak alkaline pH and then keeping the dispersion at 0 to 50 0 C for about 0.5 to 48 hours.
- a microcapsule is produced in the form of a water suspension.
- the water suspension of the microcapsule thus produced can be subjected to centrifugation, filtration or spray drying to obtain a powder formulation of the microcapsule.
- a thickening agent, an antifreezing agent, a preservative, a density regulator, a pH regulator or water can be further added.
- the microcapsule thus produced can be used, for example, as a water suspended pesticidal composition containing 0.1 to 30% by weight of a pesticidal compound.
- Examples of the thickening agent include those described above.
- Examples of the antifreezing agent include propylene glycol.
- Examples of the preservative include p-hydroxybenzoic acid esters; isothiazoline derivatives such as 5-chloro-2-methyl-4-isothiazolin-3-one and 2-methyl-4-isothiazolin-3-one; 2-bromo-2-nitropropane- 1,3-diol; and salicylic acid derivatives.
- Specific examples of the preservative include Biohope L (manufactured by K.I. CHEMICAL INDUSTRY CO., LTD.) and Proxel GXL (manufactured by Avecia K. K.) .
- Examples of the density regulator include water-soluble salts such as sodium sulfate and water-soluble compounds such as urea.
- Examples of the pH regulator include disodium hydrogen phosphate, dipotassium hydrogen phosphate and sodium hydroxide.
- a pesticidal composition containing the microcapsule of the present invention is sprayed on pests or habitats of pests in an amount of about 0.1 to 1,000 g/1,000 m 2 , preferably about 1 to 100 g/1,000 m 2 of the pesticidal compound.
- a microcapsule produced by a method for producing a microcapsule which comprises keeping a mixture of a pesticidal compound, a compound represented by formula (I) and a polyisocyanate at 20 to 60°C for 3 hours or more:
- R 1 represents a C1-C4 alkyl group
- R 2 represents a C1-C4 alkyl group
- the present microcapsule wherein the net volume of microcapsule particles with a particle diameter of 5 ⁇ m or less is less than 20% based on the gross volume of microcapsule particles and the net volume of microcapsule particles with a particle diameter of 50 ⁇ m or more is less than 20% based on the gross volume of microcapsule particles .
- the present microcapsule wherein the net volume of microcapsule particles with a particle diameter of 5 ⁇ m or less is less than 20% based on the gross volume of microcapsule particles, the net volume of microcapsule particles with a particle diameter of 50 ⁇ m or more is less than 20% based on the gross volume of microcapsule particles, and the ratio of volume median diameter/film thickness is from 25 to 150.
- the present microcapsule wherein the net volume of microcapsule particles with a particle diameter of 5 ⁇ m or less is less than 20% based on the gross volume of microcapsule particles, the net volume of microcapsule particles with a particle diameter of 50 ⁇ m or more is less than 20% based on the gross volume of microcapsule particles, and the film is made of polyurethane .
- the present microcapsule wherein the net volume of microcapsule particles with a particle diameter of 5 ⁇ m or less is less than 20% based on the gross volume of microcapsule particles, the net volume of microcapsule particles with a particle diameter of 50 ⁇ m or more is less than 20% based on the gross volume of microcapsule particles, the ratio of volume median diameter/film thickness is from 25 to 150, and the film is made of polyurethane .
- the present microcapsule wherein the weight ratio of the pesticidal compound to the compound represented by formula (I) is from 20:100 to 40:100, the net volume of microcapsule particles with a particle diameter of 5 ⁇ m or less is less than 20% based on the gross volume of microcapsule particles, and the net volume of microcapsule particles with a particle diameter of 50 ⁇ m or more is less than 20% based on the gross volume of microcapsule particles .
- the present microcapsule wherein the weight ratio of the pesticidal compound to the compound represented by formula (I) is from 20:100 to 40:100, the net volume of microcapsule particles with a particle diameter of 5 ⁇ m or less is less than 20% based on the gross volume of microcapsule particles, the net volume of microcapsule particles with a particle diameter of 50 ⁇ m or more is less than 20% based on the gross volume of microcapsule particles, and the ratio of volume median diameter/film thickness is from 25 to 150.
- the present microcapsule wherein the weight ratio of the pesticidal compound to the compound represented by formula (I) is from 20:100 to 40:100, the net volume of microcapsule particles with a particle diameter of 5 ⁇ m or less is less than 20% based on the gross volume of microcapsule particles, the net volume of microcapsule particles with a particle diameter of 50 ⁇ m or more is less than 20% based on the gross volume of microcapsule particles, and the film is made of polyurethane .
- the present microcapsule wherein the weight ratio of the pesticidal compound to the compound represented by formula (I) is from 20:100 to 40:100, the net volume of microcapsule particles with a particle diameter of 5 ⁇ m or less is less than 20% based on the gross volume of microcapsule particles, the net volume of microcapsule particles with a particle diameter of 50 ⁇ m or more is less than 20% based on the gross volume of microcapsule particles, the ratio of volume median diameter/film thickness is from 25 to 150, and the film is made of polyurethane .
- the present microcapsule which contains an isothiazoline derivative as a preservative, and wherein the net volume of microcapsule particles with a particle diameter of 5 ⁇ m or less is less than 20% based on the gross volume of microcapsule particles and the net volume of microcapsule particles with a particle diameter of 50 ⁇ m or more is less than 20% based on the gross volume of microcapsule particles.
- the present microcapsule which contains an isothiazoline derivative as a preservative, and wherein the net volume of microcapsule particles with a particle diameter of 5 ⁇ m or less is less than 20% based on the gross volume of microcapsule particles, the net volume of microcapsule particles with a particle diameter of 50 ⁇ m or more is less than 20% based on the gross volume of microcapsule particles, and the ratio of volume median diameter/film thickness is from 25 to 150.
- the present microcapsule which contains an isothiazoline derivative as a preservative, and wherein the net volume of microcapsule particles with a particle diameter of 5 ⁇ m or less is less than 20% based on the gross volume of microcapsule particles, the net volume of microcapsule particles with a particle diameter of 50 ⁇ m or more is less than 20% based on the gross volume of microcapsule particles, and the film is made of polyurethane .
- the present microcapsule which contains an isothiazoline derivative as a preservative, and wherein the net volume of microcapsule particles with a particle diameter of 5 ⁇ m or less is less than 20% based on the gross volume of microcapsule particles, the net volume of microcapsule particles with a particle diameter of 50 ⁇ m or more is less than 20% based on the gross volume of microcapsule particles, the ratio of volume median diameter/film thickness is from 25 to 150, and the film is made of polyurethane.
- the present microcapsule which contains an isothiazoline derivative as a preservative, and wherein the weight ratio of the pesticidal compound to the compound represented by formula (I) is from 20:100 to 40:100, the net volume of microcapsule particles with a particle diameter of 5 ⁇ m or less is less than 20% based on the gross volume of microcapsule particles, and the net volume of microcapsule particles with a particle diameter of 50 ⁇ m or more is less than 20% based on the gross volume of microcapsule particles .
- the present microcapsule which contains an isothiazoline derivative as a preservative, and wherein the weight ratio of the pesticidal compound to the compound represented by formula (I) is from 20:100 to 40:100, the net volume of microcapsule particles with a particle diameter of 5 ⁇ m or less is less than 20% based on the gross volume of microcapsule particles, the net volume of microcapsule particles with a particle diameter of 50 ⁇ m or more is less than 20% based on the gross volume of microcapsule particles, and the ratio of volume median diameter/film thickness is from 25 to 150.
- the present microcapsule which contains an isothiazoline derivative as a preservative, and wherein the weight ratio of the pesticidal compound to the compound represented by formula (I) is from 20:100 to 40:100, the net volume of microcapsule particles with a particle diameter of 5 ⁇ m or less is less than 20% based on the gross volume of microcapsule particles, the net volume of microcapsule particles with a particle diameter of 50 ⁇ m or more is less than 20% based on the gross volume of microcapsule particles, and the film is made of polyurethane .
- the present microcapsule which contains an isothiazoline derivative as a preservative, and wherein the weight ratio of the pesticidal compound to the compound represented by formula (I) is from 20:100 to 40:100, the net volume of microcapsule particles with a particle diameter of 5 ⁇ m or less is less than 20% based on the gross volume of microcapsule particles, the net volume of microcapsule particles with a particle diameter of 50 ⁇ m or more is less than 20% based on the gross volume of microcapsule particles, the ratio of volume median diameter/film thickness is from 25 to 150, and the film is made of polyurethane.
- the present microcapsule which contains a pH regulator and an isothiazoline derivative as a preservative, and wherein the net volume of microcapsule particles with a particle diameter of 5 ⁇ m or less is less than 20% based on the gross volume of microcapsule particles and the net volume of microcapsule particles with a particle diameter of 50 ⁇ m or more is less than 20% based on the gross volume of microcapsule particles.
- the present microcapsule which contains a pH regulator and an isothiazoline derivative as a preservative, and wherein the net volume of microcapsule particles with a particle diameter of 5 ⁇ m or less is less than 20% based on the gross volume of microcapsule particles, the net volume of microcapsule particles with a particle diameter of 50 ⁇ m or more is less than 20% based on the gross volume of microcapsule particles, and the ratio of volume median diameter/film thickness is from 25 to 150.
- the present microcapsule which contains a pH regulator and an isothiazoline derivative as a preservative, and wherein the net volume of microcapsule particles with a particle diameter of 5 ⁇ m or less is less than 20% based on the gross volume of microcapsule particles, the net volume of microcapsule particles with a particle diameter of 50 ⁇ m or more is less than 20% based on the gross volume of microcapsule particles, and the film is made of polyurethane .
- the present microcapsule which contains a pH regulator and an isothiazoline derivative as a preservative, and wherein the net volume of microcapsule particles with a particle diameter of 5 ⁇ m or less is less than 20% based on the gross volume of microcapsule particles, the net volume of microcapsule particles with a particle diameter of 50 ⁇ m or more is less than 20% based on the gross volume of microcapsule particles, the ratio of volume median diameter/film thickness is from 25 to 150, and the film is made of polyurethane .
- the present microcapsule which contains a pH regulator and an isothiazoline derivative as a preservative, and wherein the weight ratio of the pesticidal compound to the compound represented by formula (I) is from 20:100 to 40:100, the net volume of microcapsule particles with a particle diameter of 5 ⁇ m or less is less than 20% based on the gross volume of microcapsule particles, and the net volume of microcapsule particles with a particle diameter of 50 ⁇ m or more is less than 20% based on the gross volume of microcapsule particles.
- the present microcapsule which contains a pH regulator and an isothiazoline derivative as a preservative, and wherein the weight ratio of the pesticidal compound to the compound represented by formula (I) is from 20:100 to 40:100, the net volume of microcapsule particles with a particle diameter of 5 ⁇ m or less is less than 20% based on the gross volume of microcapsule particles, the net volume of microcapsule particles with a particle diameter of 50 ⁇ m or more is less than 20% based on the gross volume of microcapsule particles, and the ratio of volume median diameter/film thickness is from 25 to 150.
- the present microcapsule which contains a pH regulator and an isothiazoline derivative as a preservative, and wherein the weight ratio of the pesticidal compound to the compound represented by formula (I) is from 20:100 to 40:100, the net volume of microcapsule particles with a particle diameter of 5 ⁇ m or less is less than 20% based on the gross volume of microcapsule particles, the net volume of microcapsule particles with a particle diameter of 50 ⁇ m or more is less than 20% based on the gross volume of microcapsule particles, and the film is made of polyurethane .
- the present microcapsule which contains a pH regulator and an isothiazoline derivative as a preservative, and wherein the weight ratio of the pesticidal compound to the compound represented by formula (I) is from 20:100 to 40:100, the net volume of microcapsule particles with a particle diameter of 5 ⁇ m or less is less than 20% based on the gross volume of microcapsule particles, the net volume of microcapsule particles with a particle diameter of 50 ⁇ m or more is less than 20% based on the gross volume of microcapsule particles, the ratio of volume median diameter/film thickness is from 25 to 150, and the film is made of polyurethane.
- MASCHINENFABRIK vessel size: 600 mL, filled with 1,150 g of spherical glass of 1 mm diameter, revolution speed of impeller: 12 m/sec as a peripheral speed) at a rate of 3 L/hr to further grind the clothianidin particles (the resultant mixture is referred to as the mixture 1-3) .
- the clothianidin particles in the mixture 1-3 had a volume median diameter of 2.4 ⁇ m, wherein the net volume of the particles with a diameter of 10 ⁇ m or more was 1.6% based on the gross volume of microcapsule particles.
- the mixture 1-4 was kept at 20 0 C for 24 hours (the resultant mixture is referred to as the mixture 1-5) .
- the mixture 1-6 was stirred with a homogenizer (T. K. Autohomomixer, manufactured by PRIMIX CORP., revolution speed: 9,000 rpm) at room temperature to form liquid droplets in water (the resultant mixture is referred to as the mixture 1-7) .
- a homogenizer T. K. Autohomomixer, manufactured by PRIMIX CORP., revolution speed: 9,000 rpm
- the mixture 1-7 was stirred at 60 0 C for 24 hours to give an aqueous suspension composition of clothianidin microcapsules (hereinafter, referred to as the aqueous suspension composition 1).
- the resultant microcapsules had a volume median diameter of 20.9 ⁇ m, wherein the net volume of the microcapsules with a particle diameter of 5 ⁇ m or less was 8.9% based on the gross volume of microcapsule particles, and the net volume of the microcapsules with a particle diameter of 50 ⁇ m or more was 0% based on the gross volume of microcapsule particles.
- the mixture 2-1 250 g of clothianidin and 750 g of methyl 0- acetylricinoleate (Ricsizer C-101, manufactured by Itoh Oil Chemicals Co., Ltd., content: 95.5%) were mixed (the resultant mixture is referred to as the mixture 2-1) .
- the mixture 2-1 was stirred with a rotor-stator homogenizer (Polytron Homogenizer, manufactured by KINEMATICA AG) to grind clothianidin contained in the mixture 2-1 for about 10 minutes (the resultant mixture is referred to as the mixture 2-2) .
- the clothianidin particles in the mixture 2- 2 had a volume median diameter of 0.5 mm.
- the mixture 2-2 was fed into Dyno Mill (manufactured by WILLY A. BACHOFEN AG. MASCHINENFABRIK, vessel size: 600 mL, filled with 1,150 g of spherical glass of 1 mm diameter, revolution speed of impeller: 12 m/sec as a peripheral speed) at a rate of 3 L/hr to further grind the clothianidin particles (the resultant mixture is referred to as the mixture 2-3) .
- the clothianidin particles in the mixture 2-3 had a volume median diameter of 2.7 ⁇ m, wherein the net volume of the particles with a diameter of 10 ⁇ m or more was 1.9% based on the gross volume of microcapsule particles .
- the mixture 2-3 was added 21.6 g of a polyisocyanate (Sumidur L-75, adduct of trimethylolpropane and toluenediisocyanate, manufactured by SUMIKA BAYER URETHANE CO., LTD.) at 40 0 C (the resultant mixture is referred to as the a mixture 2-4) .
- the mixture 2-4 was kept at 40 0 C for 5 hours (the resultant mixture is referred to as the mixture 2-5) .
- the mixture 2-6 was stirred with a homogenizer (T. K. Autohomomixer, manufactured by PRIMIX CORP., revolution speed: 9,000 rpm) at room temperature to form liquid droplets in water (the resultant mixture is referred to as the mixture 2-7) .
- a homogenizer T. K. Autohomomixer, manufactured by PRIMIX CORP., revolution speed: 9,000 rpm
- the mixture 2-7 was stirred at 6O 0 C for 24 hours to give an aqueous suspension composition of clothianidin microcapsules (hereinafter, referred to as the aqueous suspension composition 2) .
- the resultant microcapsules had a volume median diameter of 17.7 ⁇ m, wherein the net volume of the microcapsules with a particle diameter of 5 ⁇ m or less was 11.6% based on the gross volume of microcapsule particles, and the net volume of the microcapsules with a particle diameter of 50 ⁇ m or more was 0% based on the gross volume of microcapsule particles.
- the mixture 3- 1 250 g of clothianidin and 750 g of methyl O- acetylricinoleate (Ricsizer C-IOl, manufactured by Itoh Oil Chemicals Co., Ltd., content: 95.5%) were mixed (the resultant mixture is referred to as the mixture 3-1).
- the mixture 3-1 was stirred with a rotor-stator homogenizer (Polytron Homogenizer, manufactured by KINEMATICA AG) to grind clothianidin contained in the mixture 3-1 for about 10 minutes (the resultant mixture is referred to as the mixture 3-2) .
- the clothianidin particles in the mixture 3- 2 had a volume median diameter of 0.5 mm.
- the mixture 3-2 was fed into Dyno Mill (manufactured by WILLY A. BACHOFEN AG. MASCHINENFABRIK, vessel size: 600 mL, filled with 1,150 g of spherical glass of 1 mm diameter, revolution speed of impeller: 12 m/sec as a peripheral speed) at a rate of 3 L/hr to further grind the clothianidin particles (the resultant mixture is referred to as the mixture 3-3) .
- the clothianidin particles in the mixture 3-3 had a volume median diameter of 2.5 ⁇ m, wherein the net volume of the particles with a diameter of 10 ⁇ m or more was 1.8% based on the gross volume of microcapsule particles .
- the mixture 3-3 To 100 g of the mixture 3-3 was added 21.6 g of a polyisocyanate (Sumidur L-75, adduct of trimethylolpropane and toluenediisocyanate, manufactured by SUMIKA BAYER URETHANE CO., LTD.) at 30 0 C (the resultant mixture is referred to as the mixture 3-4) .
- the mixture 3-4 was kept at 30°C for 20 hours (the resultant mixture is referred to as the mixture 3-5) .
- the mixture 3-6 was stirred with a homogenizer (T. K. Autohomomixer, manufactured by PRIMIX CORP., revolution speed: 9,000 rpm) at room temperature to form liquid droplets in water (the resultant mixture is referred to as the mixture 3-7) .
- a homogenizer T. K. Autohomomixer, manufactured by PRIMIX CORP., revolution speed: 9,000 rpm
- the mixture 3-7 was stirred at 60 0 C for 24 hours to give an aqueous suspension composition of clothianidin microcapsules (hereinafter, referred to as the aqueous suspension composition 3) .
- the resultant microcapsules had a volume median diameter of 22.5 ⁇ m, wherein the net volume of the microcapsules with a diameter of 5 ⁇ m or less was 7.9% based on the gross volume of microcapsule particles, and the net volume of the microcapsules with a diameter of 50 ⁇ m or more was 0.4% based on the gross volume of microcapsule particles.
- the clothianidin particles in the mixture 4- 2 had a volume median diameter of 0.5 mm.
- the mixture 4-2 was fed into Dyno Mill (manufactured by WILLY A. BACHOFEN AG. MASCHINENFABRIK, vessel size: 600 mL, filled with 1,150 g of spherical glass of 1 mm diameter, revolution speed of impeller: 12 m/sec as a peripheral speed) at a rate of 3 L/hr to further grind the clothianidin particles (the resultant mixture is referred to as the mixture 4-3) .
- the clothianidin particles in the mixture 4-3 had a volume median diameter of 2.5 ⁇ m, wherein the net volume of the particles with a diameter of 10 ⁇ m or more was 1.8% based on the gross volume of microcapsule particles .
- the mixture 4-3 was added 9.8 g of a polyisocyanate (Sumidur L-75, adduct of trimethylolpropane and toluenediisocyanate, manufactured by SUMIKA BAYER URETHANE CO., LTD.) was added at 40 0 C (the resultant mixture is referred to as the mixture 4-4) .
- the mixture 4- 4 was kept at 40 0 C for 20 hours (the resultant mixture is referred to as the mixture 4-5) .
- aqueous suspension composition 4 To 108.8 g of water (deionized water) were added 5.6 g of ethylene glycol and 12.6 g of gum arabic (Arabic Cole SS manufactured by SAN-EI YAKUHIN BOEKI CO., LTD.) to prepare an aqueous phase. All of the aqueous phase and all of the mixture 4-5 were mixed (the resultant mixture is referred to as the mixture 4-6) .
- the mixture 4-6 was stirred with a homogenizer (T. K. Autohomomixer, manufactured by PRIMIX CORP., revolution speed: 9,000 rpm) at room temperature to form liquid droplets in water (the resultant mixture is referred to as the mixture 4-7) .
- the mixture 4-7 was stirred at 60 0 C for 24 hours to give an aqueous suspension composition of clothianidin microcapsules (hereinafter, referred to as the aqueous suspension composition 4).
- the resultant microcapsules had a volume median diameter of 19.8 ⁇ m, wherein the net volume of the microcapsules with a diameter of 5 ⁇ m or less was 9.4% based on the gross volume of microcapsule particles, and the net volume of the microcapsules with a diameter of 50 ⁇ m or more was 0.4% based on the gross volume of microcapsule particles.
- the clothianidin particles in the mixture 5- 2 had a volume median diameter of 0.5 mm.
- the mixture 5-2 was fed into Dyno Mill (manufactured by WILLY A. BACHOFEN AG. MASCHINENFABRIK, vessel size: 600 mL, filled with 1,150 g of spherical glass of 1 mm diameter, revolution speed of impeller: 12 m/sec as a peripheral speed) at a rate of 3 L/hr to further grind the clothianidin particles (the resultant mixture is referred to as the mixture 5-3).
- the clothianidin particles in the mixture 5-3 had a volume median diameter of 2.9 ⁇ m, wherein the net volume of the particles with a diameter of 10 ⁇ m or more was 3.4% based on the gross volume of microcapsule particles .
- the mixture 5-3 To 100 g of the mixture 5-3 was added 21.6 g of a polyisocyanate (Sumidur L-75, adduct of trimethylolpropane and toluenediisocyanate, manufactured by SUMIKA BAYER URETHANE CO., LTD.) at 4O 0 C (the resultant mixture is referred to as the mixture 5-4) .
- the mixture 5-4 was kept at 40 0 C for 10 hours (the resultant mixture is referred to as the mixture 5-5) .
- the mixture 5-6 was stirred with a homogenizer (T. K. Autohomomixer, manufactured by PRIMIX CORP., revolution speed: 9,000 rpm) at room temperature to form liquid droplets in water (the resultant mixture is referred to as the mixture 5-7) .
- a homogenizer T. K. Autohomomixer, manufactured by PRIMIX CORP., revolution speed: 9,000 rpm
- the mixture 5-7 was stirred at 6O 0 C for 24 hours to give an aqueous suspension composition of clothianidin microcapsules (hereinafter, referred to as the aqueous suspension composition 5).
- the resultant microcapsules had a volume median diameter of 19.6 ⁇ m, wherein the net volume of the microcapsules with a diameter of 5 ⁇ m or less was 9.1% based on the gross volume of microcapsule particles, and the net volume of the microcapsules with a diameter of 50 ⁇ m or more was 0.3% based on the gross volume of microcapsule particles.
- MASCHINENFABRIK vessel size: 600 mL, filled with 1,150 g of spherical glass of 1 mm diameter, revolution speed of impeller: 12 m/sec as a peripheral speed) at a rate of 3 L/hr to further grind the clothianidin particles (the resultant mixture is referred to as the mixture 6-3) .
- the clothianidin particles in the mixture 6-3 had a volume median diameter of 2.9 ⁇ m, wherein the net volume of the particles with a diameter of 10 ⁇ m or more was 3.4% based on the gross volume of microcapsule particles.
- the mixture 6-3 was added 21.6 g of a polyisocyanate (Sumidur L-75, adduct of trimethylolpropane and toluenediisocyanate, manufactured by SUMIKA BAYER URETHANE CO., LTD.) at 60 0 C (the resultant mixture is referred to as the mixture 6-4) .
- the mixture 6-4 was kept at 60 0 C for 3 hours (the resultant mixture is referred to as the mixture 6-5) .
- the mixture 6-6 was stirred with a homogenizer (T. K. Autohomomixer, manufactured by PRIMIX CORP., revolution speed: 9,000 rpm) at room temperature to form liquid droplets in water (the resultant mixture is referred to as the mixture 6-7) .
- a homogenizer T. K. Autohomomixer, manufactured by PRIMIX CORP., revolution speed: 9,000 rpm
- the mixture 6-7 was stirred at 60 0 C for 24 hours to give an aqueous suspension composition of clothianidin microcapsules (hereinafter, referred to as the aqueous suspension composition 6) .
- the resultant microcapsules had a volume median diameter of 21.9 ⁇ m, wherein the net volume of the microcapsules with a diameter of 5 ⁇ m or less was 8.6% based on the gross volume of microcapsule particles, and the net volume of the microcapsules with a diameter of 50 ⁇ m or more was 0.1% based on the gross volume of microcapsule particles.
- the clothianidin particles in the mixture 7- 2 had a volume median diameter of 0.4 mm.
- the mixture 7-2 was fed into Dyno Mill (manufactured by WILLY A. BACHOFEN AG. MASCHINENFABRIK, vessel size: 600 mL, filled with 1,150 g of spherical glass of 1 mm diameter, revolution speed of impeller: 12 m/sec as a peripheral speed) at a rate of 3 L/hr to further grind the clothianidin particles (the resultant mixture is referred to as the mixture 7-3) .
- the clothianidin particles in the mixture 7-3 had a volume median diameter of 2.5 ⁇ m, wherein the net volume of the particles with a diameter of 10 ⁇ m or more wad 1.8% based on the gross volume of microcapsule particles .
- the mixture 7-3 was added 21.6 g of a polyisocyanate (Sumidur L-75, adduct of trimethylolpropane and toluenediisocyanate, manufactured by SUMIKA BAYER URETHANE CO., LTD.) at 25°C (the resultant mixture is referred to as the mixture 7-4) .
- the mixture 7-4 was kept at 25°C for 20 hours (the resultant mixture is referred to as the mixture 7-5) .
- the mixture 7-7 was stirred at 6O 0 C for 24 hours to give an aqueous suspension composition of clothianidin microcapsules (hereinafter, referred to as the aqueous suspension composition 7).
- the resultant microcapsules had a volume median diameter of 13.6 ⁇ m, wherein the net volume of the microcapsules with a diameter of 5 ⁇ m or less was 15.9% based on the gross volume of microcapsule particles, and the net volume of the microcapsules with a diameter of 50 ⁇ m or more was 0% based on the gross volume of microcapsule particles .
- the clothianidin particles in the mixture 8- 2 had a volume median diameter of 0.4 mm.
- the mixture 8-2 was fed into Dyno Mill (manufactured by WILLY A. BACHOFEN AG. MASCHINENFABRIK, vessel size: 600 inL, filled with 1,150 g of spherical glass of 1 mm diameter, revolution speed of impeller: 12 m/sec as a peripheral speed) at a rate of 3 L/hr to further grind the clothianidin particles (the resultant mixture is referred to as the mixture 8-3) .
- the clothianidin particles in the mixture 8-3 had a volume median diameter of 2.5 ⁇ m, wherein the net volume of the particles with a diameter of 10 ⁇ m or more was 1.8% based on the gross volume of microcapsule particles .
- the mixture 8-3 To 100 g of the mixture 8-3 was added 21.6 g of a polyisocyanate (Sumidur L-75, adduct of trimethylolpropane and toluenediisocyanate, manufactured by SUMIKA BAYER URETHANE CO., LTD.) at 25°C (the resultant mixture is referred to as the mixture 8-4) .
- the mixture 8-4 was kept at 25°C for 20 hours (the resultant mixture is referred to as the mixture 8-5) .
- the mixture 8-6 was stirred with a homogenizer (T. K. Autohomomixer, manufactured by PRIMIX CORP., revolution speed: 7,000 rpm) at room temperature to form liquid droplets in water (the resultant mixture is referred to as the mixture 8-7) .
- a homogenizer T. K. Autohomomixer, manufactured by PRIMIX CORP., revolution speed: 7,000 rpm
- the mixture 8-7 was stirred at 60°C for 24 hours to give an aqueous suspension composition of clothianidin microcapsules (hereinafter, referred to as the aqueous suspension composition 8).
- the resultant microcapsules had a volume median diameter of 34.9 ⁇ m, wherein the net volume of the microcapsules with a diameter of 5 ⁇ m or less was 0% based on the gross volume of microcapsule particles, and the net volume of the microcapsules with a particle diameter of 50 ⁇ m or more was 16.9% based on the gross volume of microcapsule particles.
- the resultant mixture is referred to as the mixture 9-1) .
- the mixture 9-1 was stirred with a rotor-stator homogenizer (Polytron Homogenizer, manufactured by KINEMATICA AG) to grind clothianidin contained in the mixture 9-1 for about 10 minutes (the resultant mixture is referred to as the mixture 9-2) .
- the clothianidin particles in the mixture 9- 2 had a volume median diameter of 0.6 mm.
- the mixture 9-2 was fed into Dyno Mill (manufactured by WILLY A. BACHOFEN AG. MASCHINENFABRIK, vessel size: 600 mL, filled with 1,150 g of spherical glass of 1 mm diameter, revolution speed of impeller: 12 m/sec as a peripheral speed) at a rate of 3 L/hr to further grind the clothianidin particles (the resultant mixture is referred to as the mixture 9-3).
- the clothianidin particles in the mixture 9-3 had a volume median diameter of 2.0 ⁇ m, wherein the net volume of the particles with a diameter of 10 ⁇ m or more was 0% based on the gross volume of microcapsule particles .
- the mixture 9-3 To 100 g of the mixture 9-3 was added 21.6 g of a polyisocyanate (Sumidur L-75, adduct of trimethylolpropane and toluenediisocyanate, manufactured by SUMIKA BAYER URETHANE CO., LTD.) at 25°C (the resultant mixture is referred to as the mixture 9-4) .
- the mixture 9-4 was kept at 25 0 C for 20 hours (the resultant mixture is referred to as the mixture 9-5) .
- aqueous suspension composition 9 To 108.8 g of water (deionized water) were added 12.4 g of ethylene glycol and 12.6 g of gum arabic (Arabic Cole SS manufactured by SAN-EI YAKUHIN BOEKI CO., LTD.) to prepare an aqueous phase. All of the aqueous phase and all of the mixture 9-5 were mixed (the resultant mixture is referred to as the mixture 9-6) .
- the mixture 9-6 was stirred with a homogenizer (T. K. Autohomomixer, manufactured by PRIMIX CORP., revolution speed: 9,000 rpm) at room temperature to form liquid droplets in water (the resultant mixture is referred to as the mixture 9-7) .
- the mixture 9-7 was stirred at 60 0 C for 24 hours to give an aqueous suspension composition of clothianidin microcapsules (hereinafter, referred to as the an aqueous suspension composition 9) .
- the resultant microcapsules had a volume median diameter of 18.4 ⁇ m, wherein the net volume of the microcapsules with a particle diameter of 5 ⁇ m or less was 11.2% based on the gross volume of microcapsule particles, and the net volume of the microcapsules with s particle diameter of 50 ⁇ m or more was 0% based on the gross volume of microcapsule particles.
- the clothianidin particles in the mixture 10-2 had a volume median diameter of 0.4 mm.
- the mixture 10-2 was fed into Dyno Mill (manufactured by WILLY A. BACHOFEN AG. MASCHINENFABRIK, vessel size: 600 mL, filled with 1,150 g of spherical glass of 1 mm diameter, revolution speed of impeller: 12 m/sec as a peripheral speed) at a rate of 3 L/hr to further grind the clothianidin particles (the resultant mixture is referred to as the mixture 10-3) .
- the clothianidin particles in the mixture 10-3 had a volume median diameter of 2.9 ⁇ m, wherein the net volume of the particles with a diameter of 10 ⁇ m or more was 3.3% based on the gross volume of microcapsule particles.
- the mixture 10-3 To 100 g of the mixture 10-3 was added 21.6 g of a polyisocyanate (Sumidur L-75, adduct of trimethylolpropane and toluenediisocyanate, manufactured by SUMIKA BAYER URETHANE CO., LTD.) at 25°C (the resultant mixture is referred to as the mixture 10-4) .
- the mixture 10-4 was kept at 25°C for 20 hours (the resultant mixture is referred to as the mixture 10-5) .
- the mixture 10-6 was stirred with a homogenizer (T. K. Autohomomixer, manufactured by PRIMIX CORP., revolution speed: 9,000 rpm) at room temperature to form liquid droplets in water (the resultant mixture is referred to as the mixture 10-7) .
- a homogenizer T. K. Autohomomixer, manufactured by PRIMIX CORP., revolution speed: 9,000 rpm
- the mixture 10-7 was stirred at 60 0 C for 24 hours to give an aqueous suspension composition of clothianidin microcapsules (hereinafter, referred to as the aqueous suspension composition 10) .
- the resultant microcapsules had a volume median diameter of 19.9 ⁇ m, wherein the net volume of the microcapsules with a particle diameter of 5 ⁇ m or less was 9.4% based on the gross volume of microcapsule particles, and the net volume of the microcapsules with a particle diameter of 50 ⁇ m or more was 0% based on the gross volume of microcapsule particles.
- the mixture 11-2 was fed into Dyno Mill (manufactured by WILLY A. BACHOFEN AG. MASCHINENFABRIK, vessel size: 600 mL, filled with 1,150 g of spherical glass of 1 mm diameter, revolution speed of impeller: 12 m/sec as a peripheral speed) at a rate of 3 L/hr to further grind the clothianidin particles (the resultant mixture is referred to as the mixture 11-3) .
- the clothianidin particles in the mixture 11-3 had a volume median diameter of 2.9 ⁇ m, wherein the net volume of the particles with a diameter of 10 ⁇ m or more was 3.3% based on the gross volume of microcapsule particles.
- the mixture 11-3 was added 21.6 g of a polyisocyanate (Sumidur L-75, adduct of trimethylolpropane and toluenediisocyanate, manufactured by SUMIKA BAYER URETHANE CO., LTD.) at 25°C (the resultant mixture is ' referred to as the mixture 11-4) .
- the mixture 11-4 was kept at 25°C for 20 hours (the resultant mixture is referred to as the mixture 11-5) .
- the mixture 11-6 was stirred with a homogenizer (T. K. Autohomomixer, manufactured by PRIMIX CORP., revolution speed: 9,000 rpm) at room temperature to form liquid droplets in water (the resultant mixture is referred to as the mixture 11-7).
- a homogenizer T. K. Autohomomixer, manufactured by PRIMIX CORP., revolution speed: 9,000 rpm
- the mixture 11-7 was stirred at 60 0 C for 24 hours to give an aqueous suspension composition of clothianidin microcapsules (hereinafter, referred to as the aqueous suspension composition 11).
- the resultant microcapsules had a volume median diameter of 19.9 ⁇ m, wherein the net volume of the microcapsules with a particle diameter of 5 ⁇ m or less was
- the aqueous suspension composition 11 was mixed with an aqueous solution prepared by mixing 68.05 g of water, 0.05 g of xanthan gum, 0.1 g of aluminum magnesium silicate, 0.5 g of disodium hydrogen phosphate and 0.1 g of Biohope L (preservative, manufactured by K.I. CHEMICAL INDUSTRY CO., LTD.) to give an aqueous suspension formulation of microcapsules.
- the aqueous suspension formulation had pH 7.9.
- MASCHINENFABRIK vessel size: 600 mL, filled with 1,150 g of spherical glass of 1 mm diameter, revolution speed of impeller: 12 m/sec as a peripheral speed) at a rate of 3 L/hr to further grind the clothianidin particles (the resultant mixture is referred to as the mixture 12-3) .
- the clothianidin particles in the mixture 12-3 had a volume median diameter of 2.9 ⁇ m, wherein the net volume of the particles with a diameter of 10 ⁇ m or more was 3.3% based on the gross volume of microcapsule particles.
- the mixture 12-3 was added 21.6 g of a polyisocyanate (Sumidur L-75, adduct of trimethylolpropane and toluenediisocyanate, manufactured by SUMIKA BAYER URETHANE CO., LTD.) at 25 0 C (the resultant mixture is referred to as the mixture 12-4) .
- the mixture 12-4 was kept at 25°C for 20 hours (the resultant mixture is referred to as the mixture 12-5) .
- the mixture 12-6 was stirred with a homogenizer (T. K. Autohomomixer, manufactured by PRIMIX CORP., revolution speed: 9,000 rpm) at room temperature to form liquid droplets in water (the resultant mixture is referred to as the mixture 12-7) .
- a homogenizer T. K. Autohomomixer, manufactured by PRIMIX CORP., revolution speed: 9,000 rpm
- the mixture 12-7 was stirred at 60 0 C for 24 hours to give an aqueous suspension composition of clothianidin microcapsules (hereinafter, referred to as the aqueous suspension composition 12).
- the resultant microcapsules had a volume median diameter of 19.9 ⁇ m, wherein the net volume of the microcapsules with a particle diameter of 5 ⁇ m or less was 9.4% based on the gross volume of microcapsule particles, and the net volume of the microcapsules with a particle diameter of 50 ⁇ m or more was 0% based on the gross volume of microcapsule particles.
- the aqueous suspension composition 12 was mixed with an aqueous solution prepared by mixing 68.55 g of water, 0.05 g of xanthan gum, 0.1 g of aluminum magnesium silicate, 0.1 g of sodium hydroxide and 0.1 g of Biohope L (preservative, manufactured by K.I. CHEMICAL INDUSTRY CO., LTD.) to give an aqueous suspension formulation of microcapsules.
- the aqueous suspension formulation had pH 7.9.
- MASCHINENFABRIK vessel size: 600 mL, filled with 1,150 g of spherical glass of 1 mm diameter, revolution speed of impeller: 12 m/sec as a peripheral speed) at a rate of 3 L/hr to further grind the clothianidin particles (the resultant mixture is referred to as the mixture 13-3) .
- the clothianidin particles in the mixture 13-3 had a volume median diameter of 2.9 ⁇ m, wherein the net volume of the particles with a diameter of 10 ⁇ m or more was 3.3% based on the gross volume of microcapsule particles.
- the mixture 13-3 was added 21.6 g of a polyisocyanate (Sumidur L-75, adduct of trimethylolpropane and toluenediisocyanate, manufactured by SUMIKA BAYER URETHANE CO., LTD.) at 25 0 C (the resultant mixture is referred to as the mixture 13-4) .
- the mixture 13-4 was kept at 25°C for 20 hours (the resultant mixture is referred to as the mixture 13-5) .
- the mixture 13-6 was stirred with a homogenizer (T. K. Autohomomixer, manufactured by PRIMIX CORP., revolution speed: 9,000 rpm) at room temperature to form liquid droplets in water (the resultant mixture is referred to as the mixture 13-7) .
- a homogenizer T. K. Autohomomixer, manufactured by PRIMIX CORP., revolution speed: 9,000 rpm
- the mixture 13-7 was stirred at 60 0 C for 24 hours to give an aqueous suspension composition of clothianidin microcapsules (hereinafter, referred to as the aqueous suspension composition 13).
- the resultant microcapsules had a volume median diameter of 19.9 ⁇ m, wherein the net volume of the microcapsules with a particle diameter of 5 ⁇ m or less was 9.4% based on the gross volume of microcapsule particles, and the net volume of the microcapsules with a particle diameter of 50 ⁇ m or more was 0% based on the gross volume of microcapsule particles.
- the aqueous suspension composition 13 was mixed with an aqueous solution prepared by mixing 68.05 g of water, 0.05 g of xanthan gum, 0.1 g of aluminum magnesium silicate, 0.5 g of dipotassium hydrogen phosphate and 0.1 g of Biohope L (preservative, manufactured by K.I. CHEMICAL INDUSTRY CO., LTD.) to give an aqueous suspension formulation of microcapsules.
- the aqueous suspension formulation had pH 7.2.
- MASCHINENFABRIK vessel size: 600 mL, filled with 1,150 g of spherical glass of 1 mm diameter, revolution speed of impeller: 12 m/sec as a peripheral speed) at a rate of 3 L/hr to further grind the clothianidin particles (the resultant mixture is referred to as the mixture 14-3) .
- the clothianidin particles in the mixture 14-3 had a volume median diameter of 2.9 ⁇ m, wherein the net volume of the particles with a diameter of 10 ⁇ m or more was 3.3% based on the gross volume of microcapsule particles.
- the mixture 14-3 To 100 g of the mixture 14-3 was added 21.6 g of a polyisocyanate (Sumidur L-75, adduct of trimethylolpropane and toluenediisocyanate, manufactured by SUMIKA BAYER URETHANE CO., LTD.) at 25°C (the resultant mixture is referred to as the mixture 14-4) .
- the mixture 14-4 was kept at 25°C for 20 hours (the resultant mixture is referred to as the mixture 14-5) .
- the mixture 14-6 was stirred with a homogenizer (T. K. Autohomomixer, manufactured by PRIMIX CORP., revolution speed: 9,000 rpm) at room temperature to form liquid droplets in water (the resultant mixture is referred to as the mixture 14-7) .
- a homogenizer T. K. Autohomomixer, manufactured by PRIMIX CORP., revolution speed: 9,000 rpm
- the mixture 14-7 was stirred at 6O 0 C for 24 hours to give an aqueous suspension composition of clothianidin microcapsules (hereinafter, referred to as the aqueous suspension composition 14).
- the resultant microcapsules has a volume median diameter of 19.9 ⁇ m, wherein the net volume of the microcapsules with a particle diameter of 5 ⁇ m or less was 9.4% based on the gross volume of microcapsule particles, and the net volume of the microcapsules with a particle diameter of 50 ⁇ m or more was 0% based on the gross volume of microcapsule particles.
- the aqueous suspension composition 14 was mixed with an aqueous solution prepared by mixing 68.25 g of water, 0.05 g of xanthan gum, 0.1 g of aluminum magnesium silicate, 0.3 g of disodium hydrogen phosphate and 0.1 g of Biohope L (preservative, manufactured by K.I. CHEMICAL INDUSTRY CO., LTD.) to give an aqueous suspension formulation of microcapsules.
- the aqueous suspension formulation had pH 6.2.
- MASCHINENFABRIK vessel size: 600 mL, filled with 1,150 g of spherical glass of 1 mm diameter, revolution speed of impeller: 12 m/sec as a peripheral speed) at a rate of 3 L/hr to further grind the clothianidin particles (the resultant mixture is referred to as the mixture 15-3).
- the clothianidin particles in the mixture 15-3 had a volume median diameter of 2.9 ⁇ m, wherein the net volume of the particles with a diameter of 10 ⁇ m or more wad 3.3% based on the gross volume of microcapsule particles.
- the mixture 15-3 was added 21.6 g of a polyisocyanate (Sumidur L-75, adduct of trimethylolpropane and toluenediisocyanate, manufactured by SUMIKA BAYER URETHANE CO., LTD.) at 25°C (the resultant mixture is referred to as the mixture 15-4) .
- the mixture 15-4 was kept at 25°C for 20 hours (the resultant mixture is referred to as the mixture 15-5) .
- the mixture 15-6 was stirred with a homogenizer (T. K. Autohomomixer, manufactured by PRIMIX CORP., revolution speed: 9,000 rpm) at room temperature to form liquid droplets in water (the resultant mixture is referred to as the mixture 15-7) .
- a homogenizer T. K. Autohomomixer, manufactured by PRIMIX CORP., revolution speed: 9,000 rpm
- the mixture 15-7 was stirred at 60 0 C for 24 hours to give an aqueous suspension composition of clothianidin microcapsules (hereinafter, referred to as the aqueous suspension composition 15) .
- the resultant microcapsules had a volume median diameter of 19.9 ⁇ m, wherein the net volume of the microcapsules with a particle diameter of 5 ⁇ m or less was 9.4% based on the gross volume of microcapsule particles, and the net volume of the microcapsules with a particle diameter of 50 ⁇ m or more was 0% based on the gross volume of microcapsule particles.
- the aqueous suspension composition 15 was mixed with an aqueous solution prepared by mixing 68.35 g of water, 0.05 g of xanthan gum, 0.1 g of aluminum magnesium silicate and 0.2 g of Proxel GXL (preservative, manufactured by Avecia K. K.) to give an aqueous suspension formulation of microcapsules.
- the aqueous suspension formulation had pH 7.4.
- An aqueous suspension composition (hereinafter, referred to as the comparative aqueous suspension composition 1) was produced in the same manner as in Production Example 1 except that the mixture 1-4 was kept at 20 0 C for 1 hour.
- An aqueous suspension composition (hereinafter, referred to as the comparative aqueous suspension composition 2) was produced in the same manner as in Production Example 5 except that the mixture 5-4 was kept at 40 0 C for 1 hour.
- aqueous suspension composition (hereinafter, referred to as the comparative aqueous suspension composition 3) was produced in the same manner as in
- Comparative Production Example 4 An aqueous suspension composition (hereinafter, referred to as the comparative aqueous suspension composition 4) was produced in the same manner as in Production Example 1 except that the mixture 1-4 was kept at 60 0 C for 0.5 hour. Test Example 1
- Each of the aqueous suspension compositions shown in the following Table 2 was diluted 200 times with water. Then, 0.4 mL of the dilution was spread over a glass petri dish of 6 cm diameter. Then, the dilution was air dried at room temperature. The petri dish was exposed to sunlight for 250 hours (cumulative illuminance: 1810 Lx).
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Abstract
Description
Claims
Priority Applications (10)
Application Number | Priority Date | Filing Date | Title |
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US13/320,568 US10350569B2 (en) | 2009-05-29 | 2010-05-28 | Method for producing microcapsule |
BRPI1015413-2A BRPI1015413B1 (en) | 2009-05-29 | 2010-05-28 | METHOD FOR PRODUCING THE MICROCAPSULA |
SG2011081171A SG175887A1 (en) | 2009-05-29 | 2010-05-28 | Method for producing microcapsule |
AU2010253732A AU2010253732B2 (en) | 2009-05-29 | 2010-05-28 | Method for producing microcapsule |
MX2011012443A MX2011012443A (en) | 2009-05-29 | 2010-05-28 | Method for producing microcapsule. |
CA2761500A CA2761500C (en) | 2009-05-29 | 2010-05-28 | Method for producing microcapsule |
EP10780694.5A EP2434876B1 (en) | 2009-05-29 | 2010-05-28 | Method for producing microcapsules |
ES10780694.5T ES2638508T3 (en) | 2009-05-29 | 2010-05-28 | Method for the production of microcapsules |
CN201080023634.9A CN102448293B (en) | 2009-05-29 | 2010-05-28 | Method for producing microcapsule |
ZA2011/08342A ZA201108342B (en) | 2009-05-29 | 2011-11-14 | Method for producing microcapsule |
Applications Claiming Priority (2)
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JP2009130143A JP5439952B2 (en) | 2009-05-29 | 2009-05-29 | Method for producing microcapsules |
JP2009-130143 | 2009-05-29 |
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WO2010137743A1 true WO2010137743A1 (en) | 2010-12-02 |
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PCT/JP2010/059489 WO2010137743A1 (en) | 2009-05-29 | 2010-05-28 | Method for producing microcapsule |
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US (1) | US10350569B2 (en) |
EP (1) | EP2434876B1 (en) |
JP (1) | JP5439952B2 (en) |
KR (1) | KR20120026067A (en) |
CN (1) | CN102448293B (en) |
AR (1) | AR076615A1 (en) |
AU (1) | AU2010253732B2 (en) |
BR (1) | BRPI1015413B1 (en) |
CA (1) | CA2761500C (en) |
CL (1) | CL2011003006A1 (en) |
ES (1) | ES2638508T3 (en) |
MX (1) | MX2011012443A (en) |
SG (1) | SG175887A1 (en) |
TW (1) | TWI505776B (en) |
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Cited By (5)
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WO2012057360A1 (en) | 2010-10-28 | 2012-05-03 | Sumitomo Chemical Company, Limited | Process for producing microcapsule formulation and microcapsule formulation produced by same process |
RU2488437C1 (en) * | 2012-04-19 | 2013-07-27 | Федеральное государственное бюджетное образовательное учреждение высшего профессионального образования Курская государственная сельскохозяйственная академия имени профессора И.И. Иванова Министерства сельского хозяйства Российской Федерации | Method of producing microcapsules of pesticides by nonsolvent precipitation method |
RU2516357C2 (en) * | 2012-04-19 | 2014-05-20 | Федеральное государственное бюджетное образовательное учреждение высшего профессионального образования Курская государственная сельскохозяйственная академия имени профессора И.И. Иванова Министерства сельского хозяйства Российской Федерации | Method of obtaining microcapsules of pesticides |
RU2518449C2 (en) * | 2012-04-19 | 2014-06-10 | Федеральное государственное бюджетное образовательное учреждение высшего профессионального образования Курская государственная сельскохозяйственная академия имени профессора И.И. Иванова Министерства сельского хозяйства Российской Федерации | Method of obtaining microcapsules of pesticides using physico-chemical method |
RU2540431C2 (en) * | 2012-08-31 | 2015-02-10 | Федеральное государственное бюджетное образовательное учреждение высшего профессионального образования Курская государстенная сельскохозяйственная академия имени профессора И.И. Иванова Министерства сельского хозяйства Российской Федерации | Method of obtaining microcapsules of heterocyclic compounds of triazine series |
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JP5682905B2 (en) * | 2010-08-31 | 2015-03-11 | 住化エンバイロメンタルサイエンス株式会社 | Microcapsules |
WO2020194910A1 (en) * | 2019-03-28 | 2020-10-01 | 富士フイルム株式会社 | Microcapsules, microcapsule composition, softener, and detergent |
CN110591038B (en) * | 2019-08-29 | 2021-06-29 | 威尔(福建)生物有限公司 | Preparation method and application of thickening agent for aqueous emulsion |
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- 2010-05-28 CA CA2761500A patent/CA2761500C/en not_active Expired - Fee Related
- 2010-05-28 WO PCT/JP2010/059489 patent/WO2010137743A1/en active Application Filing
- 2010-05-28 EP EP10780694.5A patent/EP2434876B1/en active Active
- 2010-05-28 AU AU2010253732A patent/AU2010253732B2/en active Active
- 2010-05-28 MX MX2011012443A patent/MX2011012443A/en active IP Right Grant
- 2010-05-28 KR KR1020117028067A patent/KR20120026067A/en not_active Application Discontinuation
- 2010-05-28 AR ARP100101863A patent/AR076615A1/en active IP Right Grant
- 2010-05-28 CN CN201080023634.9A patent/CN102448293B/en active Active
- 2010-05-28 US US13/320,568 patent/US10350569B2/en active Active
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Cited By (7)
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WO2012057360A1 (en) | 2010-10-28 | 2012-05-03 | Sumitomo Chemical Company, Limited | Process for producing microcapsule formulation and microcapsule formulation produced by same process |
EP2632252A1 (en) * | 2010-10-28 | 2013-09-04 | Sumitomo Chemical Company Limited | Process for producing microcapsule formulation and microcapsule formulation produced by same process |
EP2632252A4 (en) * | 2010-10-28 | 2014-05-07 | Sumitomo Chemical Co | Process for producing microcapsule formulation and microcapsule formulation produced by same process |
RU2488437C1 (en) * | 2012-04-19 | 2013-07-27 | Федеральное государственное бюджетное образовательное учреждение высшего профессионального образования Курская государственная сельскохозяйственная академия имени профессора И.И. Иванова Министерства сельского хозяйства Российской Федерации | Method of producing microcapsules of pesticides by nonsolvent precipitation method |
RU2516357C2 (en) * | 2012-04-19 | 2014-05-20 | Федеральное государственное бюджетное образовательное учреждение высшего профессионального образования Курская государственная сельскохозяйственная академия имени профессора И.И. Иванова Министерства сельского хозяйства Российской Федерации | Method of obtaining microcapsules of pesticides |
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RU2540431C2 (en) * | 2012-08-31 | 2015-02-10 | Федеральное государственное бюджетное образовательное учреждение высшего профессионального образования Курская государстенная сельскохозяйственная академия имени профессора И.И. Иванова Министерства сельского хозяйства Российской Федерации | Method of obtaining microcapsules of heterocyclic compounds of triazine series |
Also Published As
Publication number | Publication date |
---|---|
US10350569B2 (en) | 2019-07-16 |
EP2434876B1 (en) | 2017-08-16 |
JP5439952B2 (en) | 2014-03-12 |
JP2010275238A (en) | 2010-12-09 |
MX2011012443A (en) | 2011-12-16 |
US20120065070A1 (en) | 2012-03-15 |
TWI505776B (en) | 2015-11-01 |
ZA201108342B (en) | 2013-01-30 |
TW201100010A (en) | 2011-01-01 |
AU2010253732B2 (en) | 2015-01-22 |
CN102448293A (en) | 2012-05-09 |
AR076615A1 (en) | 2011-06-22 |
EP2434876A4 (en) | 2013-12-25 |
CN102448293B (en) | 2014-01-01 |
EP2434876A1 (en) | 2012-04-04 |
CA2761500A1 (en) | 2010-12-02 |
ES2638508T3 (en) | 2017-10-23 |
SG175887A1 (en) | 2011-12-29 |
CA2761500C (en) | 2017-05-02 |
KR20120026067A (en) | 2012-03-16 |
BRPI1015413A2 (en) | 2015-09-01 |
BRPI1015413B1 (en) | 2017-11-21 |
AU2010253732A1 (en) | 2011-12-01 |
CL2011003006A1 (en) | 2012-07-06 |
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