ZA200307178B - Microencapsulating of an agricultural active having a high melting point. - Google Patents
Microencapsulating of an agricultural active having a high melting point. Download PDFInfo
- Publication number
- ZA200307178B ZA200307178B ZA200307178A ZA200307178A ZA200307178B ZA 200307178 B ZA200307178 B ZA 200307178B ZA 200307178 A ZA200307178 A ZA 200307178A ZA 200307178 A ZA200307178 A ZA 200307178A ZA 200307178 B ZA200307178 B ZA 200307178B
- Authority
- ZA
- South Africa
- Prior art keywords
- alkylthio
- alkyl
- optionally substituted
- halo
- alkoxy
- Prior art date
Links
- 238000002844 melting Methods 0.000 title claims abstract description 122
- 230000008018 melting Effects 0.000 title claims abstract description 116
- 239000003094 microcapsule Substances 0.000 claims abstract description 146
- 238000000034 method Methods 0.000 claims abstract description 125
- 239000000203 mixture Substances 0.000 claims abstract description 116
- 239000007788 liquid Substances 0.000 claims abstract description 60
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 43
- 238000013270 controlled release Methods 0.000 claims abstract description 34
- 239000011149 active material Substances 0.000 claims abstract description 15
- 230000007613 environmental effect Effects 0.000 claims abstract description 15
- 239000003849 aromatic solvent Substances 0.000 claims abstract description 13
- -1 cyano, amino, nitro, thiocyanato, isothiocyanato, trimethylsilyl Chemical group 0.000 claims description 330
- MXMXHPPIGKYTAR-UHFFFAOYSA-N silthiofam Chemical compound CC=1SC([Si](C)(C)C)=C(C(=O)NCC=C)C=1C MXMXHPPIGKYTAR-UHFFFAOYSA-N 0.000 claims description 143
- 125000005843 halogen group Chemical group 0.000 claims description 77
- 125000004414 alkyl thio group Chemical group 0.000 claims description 73
- 125000000217 alkyl group Chemical group 0.000 claims description 62
- 239000000463 material Substances 0.000 claims description 61
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 55
- 125000003545 alkoxy group Chemical group 0.000 claims description 54
- 125000003282 alkyl amino group Chemical group 0.000 claims description 49
- 239000000243 solution Substances 0.000 claims description 48
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 46
- 229920002396 Polyurea Polymers 0.000 claims description 45
- 125000003342 alkenyl group Chemical group 0.000 claims description 44
- 125000001188 haloalkyl group Chemical group 0.000 claims description 40
- 125000000304 alkynyl group Chemical group 0.000 claims description 38
- AGGKEGLBGGJEBZ-UHFFFAOYSA-N tetramethylenedisulfotetramine Chemical compound C1N(S2(=O)=O)CN3S(=O)(=O)N1CN2C3 AGGKEGLBGGJEBZ-UHFFFAOYSA-N 0.000 claims description 38
- 150000001412 amines Chemical group 0.000 claims description 37
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 33
- 150000001875 compounds Chemical class 0.000 claims description 28
- 229910052736 halogen Inorganic materials 0.000 claims description 28
- 230000000994 depressogenic effect Effects 0.000 claims description 27
- 239000002904 solvent Substances 0.000 claims description 27
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 26
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 26
- 229920000768 polyamine Polymers 0.000 claims description 26
- 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 claims description 24
- 239000005839 Tebuconazole Substances 0.000 claims description 24
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 24
- 229910052799 carbon Inorganic materials 0.000 claims description 24
- 239000005056 polyisocyanate Substances 0.000 claims description 24
- 229920001228 polyisocyanate Polymers 0.000 claims description 24
- 241000196324 Embryophyta Species 0.000 claims description 23
- 239000012948 isocyanate Substances 0.000 claims description 23
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 22
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 22
- 150000002513 isocyanates Chemical class 0.000 claims description 22
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 21
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 21
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 20
- 229910052757 nitrogen Inorganic materials 0.000 claims description 20
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 19
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 19
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 19
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 19
- YABFPHSQTSFWQB-UHFFFAOYSA-N 2-(4-fluorophenyl)-1-(1,2,4-triazol-1-yl)-3-(trimethylsilyl)propan-2-ol Chemical compound C=1C=C(F)C=CC=1C(O)(C[Si](C)(C)C)CN1C=NC=N1 YABFPHSQTSFWQB-UHFFFAOYSA-N 0.000 claims description 18
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 18
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 18
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 18
- 125000004473 dialkylaminocarbonyl group Chemical group 0.000 claims description 17
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 claims description 16
- 229960001124 trientine Drugs 0.000 claims description 16
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 15
- 238000012695 Interfacial polymerization Methods 0.000 claims description 15
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 15
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 15
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 14
- 150000002367 halogens Chemical class 0.000 claims description 14
- 238000002156 mixing Methods 0.000 claims description 14
- 150000003839 salts Chemical class 0.000 claims description 14
- 230000009418 agronomic effect Effects 0.000 claims description 13
- 125000003118 aryl group Chemical group 0.000 claims description 13
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 12
- 125000005442 diisocyanate group Chemical group 0.000 claims description 12
- 239000000374 eutectic mixture Substances 0.000 claims description 12
- 239000000417 fungicide Substances 0.000 claims description 12
- 238000006116 polymerization reaction Methods 0.000 claims description 12
- 235000021307 Triticum Nutrition 0.000 claims description 11
- 239000004009 herbicide Substances 0.000 claims description 11
- 239000000575 pesticide Substances 0.000 claims description 11
- 229910052710 silicon Inorganic materials 0.000 claims description 11
- 229930192474 thiophene Natural products 0.000 claims description 11
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 10
- 230000000855 fungicidal effect Effects 0.000 claims description 10
- 229910052732 germanium Inorganic materials 0.000 claims description 10
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 10
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 claims description 9
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims description 9
- 239000005807 Metalaxyl Substances 0.000 claims description 9
- 239000007983 Tris buffer Substances 0.000 claims description 9
- 125000004465 cycloalkenyloxy group Chemical group 0.000 claims description 9
- 125000002541 furyl group Chemical group 0.000 claims description 9
- 230000002363 herbicidal effect Effects 0.000 claims description 9
- 229930195733 hydrocarbon Natural products 0.000 claims description 9
- 150000002430 hydrocarbons Chemical class 0.000 claims description 9
- 238000004519 manufacturing process Methods 0.000 claims description 9
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims description 9
- 125000001544 thienyl group Chemical group 0.000 claims description 9
- QZCLKYGREBVARF-UHFFFAOYSA-N Acetyl tributyl citrate Chemical compound CCCCOC(=O)CC(C(=O)OCCCC)(OC(C)=O)CC(=O)OCCCC QZCLKYGREBVARF-UHFFFAOYSA-N 0.000 claims description 8
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims description 8
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 8
- 238000006243 chemical reaction Methods 0.000 claims description 8
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 8
- 229920001451 polypropylene glycol Polymers 0.000 claims description 8
- LQDARGUHUSPFNL-UHFFFAOYSA-N 1-[2-(2,4-dichlorophenyl)-3-(1,1,2,2-tetrafluoroethoxy)propyl]1,2,4-triazole Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(COC(F)(F)C(F)F)CN1C=NC=N1 LQDARGUHUSPFNL-UHFFFAOYSA-N 0.000 claims description 7
- 239000005746 Carboxin Substances 0.000 claims description 7
- 239000005760 Difenoconazole Substances 0.000 claims description 7
- 239000005781 Fludioxonil Substances 0.000 claims description 7
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 7
- 239000005840 Tetraconazole Substances 0.000 claims description 7
- GYSSRZJIHXQEHQ-UHFFFAOYSA-N carboxin Chemical compound S1CCOC(C)=C1C(=O)NC1=CC=CC=C1 GYSSRZJIHXQEHQ-UHFFFAOYSA-N 0.000 claims description 7
- BQYJATMQXGBDHF-UHFFFAOYSA-N difenoconazole Chemical compound O1C(C)COC1(C=1C(=CC(OC=2C=CC(Cl)=CC=2)=CC=1)Cl)CN1N=CN=C1 BQYJATMQXGBDHF-UHFFFAOYSA-N 0.000 claims description 7
- MUJOIMFVNIBMKC-UHFFFAOYSA-N fludioxonil Chemical compound C=12OC(F)(F)OC2=CC=CC=1C1=CNC=C1C#N MUJOIMFVNIBMKC-UHFFFAOYSA-N 0.000 claims description 7
- 238000010438 heat treatment Methods 0.000 claims description 7
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 claims description 7
- ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical compound C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 claims description 7
- 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 claims description 7
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 7
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 6
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 claims description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
- 125000000262 haloalkenyl group Chemical group 0.000 claims description 6
- 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 claims description 5
- 239000005745 Captan Substances 0.000 claims description 5
- 239000005785 Fluquinconazole Substances 0.000 claims description 5
- 239000005843 Thiram Substances 0.000 claims description 5
- 229940117949 captan Drugs 0.000 claims description 5
- IJJVMEJXYNJXOJ-UHFFFAOYSA-N fluquinconazole Chemical compound C=1C=C(Cl)C=C(Cl)C=1N1C(=O)C2=CC(F)=CC=C2N=C1N1C=NC=N1 IJJVMEJXYNJXOJ-UHFFFAOYSA-N 0.000 claims description 5
- KUAZQDVKQLNFPE-UHFFFAOYSA-N thiram Chemical compound CN(C)C(=S)SSC(=S)N(C)C KUAZQDVKQLNFPE-UHFFFAOYSA-N 0.000 claims description 5
- 229960002447 thiram Drugs 0.000 claims description 5
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 4
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 claims description 4
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 claims description 4
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 claims description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 240000004713 Pisum sativum Species 0.000 claims description 4
- 150000001408 amides Chemical class 0.000 claims description 4
- 230000000844 anti-bacterial effect Effects 0.000 claims description 4
- 239000002635 aromatic organic solvent Substances 0.000 claims description 4
- 239000003899 bactericide agent Substances 0.000 claims description 4
- 150000002148 esters Chemical class 0.000 claims description 4
- 150000002170 ethers Chemical class 0.000 claims description 4
- 150000008282 halocarbons Chemical class 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 150000002440 hydroxy compounds Chemical class 0.000 claims description 4
- 239000002917 insecticide Substances 0.000 claims description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
- 235000021374 legumes Nutrition 0.000 claims description 4
- 239000003750 molluscacide Substances 0.000 claims description 4
- 230000002013 molluscicidal effect Effects 0.000 claims description 4
- 230000001069 nematicidal effect Effects 0.000 claims description 4
- 239000005645 nematicide Substances 0.000 claims description 4
- 150000003568 thioethers Chemical class 0.000 claims description 4
- 235000013311 vegetables Nutrition 0.000 claims description 4
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 3
- XYUINKARGUCCQJ-UHFFFAOYSA-N 3-imino-n-propylpropan-1-amine Chemical class CCCNCCC=N XYUINKARGUCCQJ-UHFFFAOYSA-N 0.000 claims description 3
- 239000004593 Epoxy Substances 0.000 claims description 3
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 claims description 3
- 239000005057 Hexamethylene diisocyanate Substances 0.000 claims description 3
- 235000017587 Medicago sativa ssp. sativa Nutrition 0.000 claims description 3
- 244000046052 Phaseolus vulgaris Species 0.000 claims description 3
- 241000219793 Trifolium Species 0.000 claims description 3
- 230000000895 acaricidal effect Effects 0.000 claims description 3
- 239000000642 acaricide Substances 0.000 claims description 3
- 125000004429 atom Chemical group 0.000 claims description 3
- 150000004985 diamines Chemical class 0.000 claims description 3
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 claims description 3
- 150000002825 nitriles Chemical group 0.000 claims description 3
- FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical compound NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 claims description 3
- ZMYFCFLJBGAQRS-IRXDYDNUSA-N (2R,3S)-epoxiconazole Chemical compound C1=CC(F)=CC=C1[C@@]1(CN2N=CN=C2)[C@H](C=2C(=CC=CC=2)Cl)O1 ZMYFCFLJBGAQRS-IRXDYDNUSA-N 0.000 claims description 2
- RYAUSSKQMZRMAI-ALOPSCKCSA-N (2S,6R)-4-[3-(4-tert-butylphenyl)-2-methylpropyl]-2,6-dimethylmorpholine Chemical compound C=1C=C(C(C)(C)C)C=CC=1CC(C)CN1C[C@H](C)O[C@H](C)C1 RYAUSSKQMZRMAI-ALOPSCKCSA-N 0.000 claims description 2
- PPDBOQMNKNNODG-NTEUORMPSA-N (5E)-5-(4-chlorobenzylidene)-2,2-dimethyl-1-(1,2,4-triazol-1-ylmethyl)cyclopentanol Chemical compound C1=NC=NN1CC1(O)C(C)(C)CC\C1=C/C1=CC=C(Cl)C=C1 PPDBOQMNKNNODG-NTEUORMPSA-N 0.000 claims description 2
- 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 claims description 2
- CKPCAYZTYMHQEX-NBVRZTHBSA-N (e)-1-(2,4-dichlorophenyl)-n-methoxy-2-pyridin-3-ylethanimine Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(=N/OC)/CC1=CC=CN=C1 CKPCAYZTYMHQEX-NBVRZTHBSA-N 0.000 claims description 2
- 239000005059 1,4-Cyclohexyldiisocyanate Substances 0.000 claims description 2
- ALQLPWJFHRMHIU-UHFFFAOYSA-N 1,4-diisocyanatobenzene Chemical compound O=C=NC1=CC=C(N=C=O)C=C1 ALQLPWJFHRMHIU-UHFFFAOYSA-N 0.000 claims description 2
- DFPJRUKWEPYFJT-UHFFFAOYSA-N 1,5-diisocyanatopentane Chemical compound O=C=NCCCCCN=C=O DFPJRUKWEPYFJT-UHFFFAOYSA-N 0.000 claims description 2
- JWUCHKBSVLQQCO-UHFFFAOYSA-N 1-(2-fluorophenyl)-1-(4-fluorophenyl)-2-(1H-1,2,4-triazol-1-yl)ethanol Chemical compound C=1C=C(F)C=CC=1C(C=1C(=CC=CC=1)F)(O)CN1C=NC=N1 JWUCHKBSVLQQCO-UHFFFAOYSA-N 0.000 claims description 2
- VGPIBGGRCVEHQZ-UHFFFAOYSA-N 1-(biphenyl-4-yloxy)-3,3-dimethyl-1-(1,2,4-triazol-1-yl)butan-2-ol Chemical compound C1=NC=NN1C(C(O)C(C)(C)C)OC(C=C1)=CC=C1C1=CC=CC=C1 VGPIBGGRCVEHQZ-UHFFFAOYSA-N 0.000 claims description 2
- WKBPZYKAUNRMKP-UHFFFAOYSA-N 1-[2-(2,4-dichlorophenyl)pentyl]1,2,4-triazole Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(CCC)CN1C=NC=N1 WKBPZYKAUNRMKP-UHFFFAOYSA-N 0.000 claims description 2
- PZBPKYOVPCNPJY-UHFFFAOYSA-N 1-[2-(allyloxy)-2-(2,4-dichlorophenyl)ethyl]imidazole Chemical compound ClC1=CC(Cl)=CC=C1C(OCC=C)CN1C=NC=C1 PZBPKYOVPCNPJY-UHFFFAOYSA-N 0.000 claims description 2
- MGNFYQILYYYUBS-UHFFFAOYSA-N 1-[3-(4-tert-butylphenyl)-2-methylpropyl]piperidine Chemical compound C=1C=C(C(C)(C)C)C=CC=1CC(C)CN1CCCCC1 MGNFYQILYYYUBS-UHFFFAOYSA-N 0.000 claims description 2
- ICLCCFKUSALICQ-UHFFFAOYSA-N 1-isocyanato-4-(4-isocyanato-3-methylphenyl)-2-methylbenzene Chemical compound C1=C(N=C=O)C(C)=CC(C=2C=C(C)C(N=C=O)=CC=2)=C1 ICLCCFKUSALICQ-UHFFFAOYSA-N 0.000 claims description 2
- KELIOZMTDOSCMM-UHFFFAOYSA-N 2,3,3a,4-tetrahydro-1-benzothiophene Chemical compound C1C=CC=C2SCCC21 KELIOZMTDOSCMM-UHFFFAOYSA-N 0.000 claims description 2
- YTOPFCCWCSOHFV-UHFFFAOYSA-N 2,6-dimethyl-4-tridecylmorpholine Chemical compound CCCCCCCCCCCCCN1CC(C)OC(C)C1 YTOPFCCWCSOHFV-UHFFFAOYSA-N 0.000 claims description 2
- STMIIPIFODONDC-UHFFFAOYSA-N 2-(2,4-dichlorophenyl)-1-(1H-1,2,4-triazol-1-yl)hexan-2-ol Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(O)(CCCC)CN1C=NC=N1 STMIIPIFODONDC-UHFFFAOYSA-N 0.000 claims description 2
- HZJKXKUJVSEEFU-UHFFFAOYSA-N 2-(4-chlorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)hexanenitrile Chemical compound C=1C=C(Cl)C=CC=1C(CCCC)(C#N)CN1C=NC=N1 HZJKXKUJVSEEFU-UHFFFAOYSA-N 0.000 claims description 2
- 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 claims description 2
- JRQLZCFSWYQHPI-UHFFFAOYSA-N 4,5-dichloro-2-cyclohexyl-1,2-thiazol-3-one Chemical compound O=C1C(Cl)=C(Cl)SN1C1CCCCC1 JRQLZCFSWYQHPI-UHFFFAOYSA-N 0.000 claims description 2
- RQDJADAKIFFEKQ-UHFFFAOYSA-N 4-(4-chlorophenyl)-2-phenyl-2-(1,2,4-triazol-1-ylmethyl)butanenitrile Chemical compound C1=CC(Cl)=CC=C1CCC(C=1C=CC=CC=1)(C#N)CN1N=CN=C1 RQDJADAKIFFEKQ-UHFFFAOYSA-N 0.000 claims description 2
- 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 claims description 2
- 239000005964 Acibenzolar-S-methyl Substances 0.000 claims description 2
- 239000005730 Azoxystrobin Substances 0.000 claims description 2
- 239000005734 Benalaxyl Substances 0.000 claims description 2
- 241000219310 Beta vulgaris subsp. vulgaris Species 0.000 claims description 2
- 240000002791 Brassica napus Species 0.000 claims description 2
- 235000004977 Brassica sinapistrum Nutrition 0.000 claims description 2
- 239000005741 Bromuconazole Substances 0.000 claims description 2
- 244000020518 Carthamus tinctorius Species 0.000 claims description 2
- 235000003255 Carthamus tinctorius Nutrition 0.000 claims description 2
- 239000005747 Chlorothalonil Substances 0.000 claims description 2
- 229920000742 Cotton Polymers 0.000 claims description 2
- 239000005757 Cyproconazole Substances 0.000 claims description 2
- 239000005758 Cyprodinil Substances 0.000 claims description 2
- VIZORQUEIQEFRT-UHFFFAOYSA-N Diethyl adipate Chemical compound CCOC(=O)CCCCC(=O)OCC VIZORQUEIQEFRT-UHFFFAOYSA-N 0.000 claims description 2
- 239000005761 Dimethomorph Substances 0.000 claims description 2
- 239000005767 Epoxiconazole Substances 0.000 claims description 2
- 239000005772 Famoxadone Substances 0.000 claims description 2
- 239000005774 Fenamidone Substances 0.000 claims description 2
- 239000005775 Fenbuconazole Substances 0.000 claims description 2
- 239000005778 Fenpropimorph Substances 0.000 claims description 2
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Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
- A01N25/26—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests in coated particulate form
- A01N25/28—Microcapsules or nanocapsules
-
- 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
- A01N55/00—Biocides, pest repellants or attractants, or plant growth regulators, containing organic compounds containing elements other than carbon, hydrogen, halogen, oxygen, nitrogen and sulfur
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Dentistry (AREA)
- Plant Pathology (AREA)
- Engineering & Computer Science (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Toxicology (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US28305301P | 2001-04-11 | 2001-04-11 |
Publications (1)
Publication Number | Publication Date |
---|---|
ZA200307178B true ZA200307178B (en) | 2005-02-14 |
Family
ID=23084281
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
ZA200307178A ZA200307178B (en) | 2001-04-11 | 2003-09-12 | Microencapsulating of an agricultural active having a high melting point. |
Country Status (14)
Country | Link |
---|---|
US (3) | US6992047B2 (pt) |
EP (1) | EP1377161B1 (pt) |
CN (2) | CN101099460A (pt) |
AT (1) | ATE330470T1 (pt) |
AU (1) | AU2002307105B2 (pt) |
BR (1) | BR0208838A (pt) |
CA (1) | CA2442585A1 (pt) |
DE (1) | DE60212603T2 (pt) |
ES (1) | ES2268073T3 (pt) |
MX (1) | MXPA03009247A (pt) |
PL (1) | PL367398A1 (pt) |
UA (1) | UA75401C2 (pt) |
WO (1) | WO2002082901A1 (pt) |
ZA (1) | ZA200307178B (pt) |
Families Citing this family (47)
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US7687434B2 (en) * | 2000-12-22 | 2010-03-30 | Monsanto Technology, Llc | Method of improving yield and vigor of plants |
US6992047B2 (en) * | 2001-04-11 | 2006-01-31 | Monsanto Technology Llc | Method of microencapsulating an agricultural active having a high melting point and uses for such materials |
MXPA04002942A (es) * | 2001-09-27 | 2004-06-21 | Monsanto Technology Llc | Composiciones fungicidas y su aplicacion en la agricultura. |
US20060286356A1 (en) | 2002-02-27 | 2006-12-21 | Thomas Toby R | Web materials with active agent |
EP1569513A1 (en) * | 2002-12-13 | 2005-09-07 | Monsanto Technology LLC | Microcapsules with amine adjusted release rates |
BRPI0508542B1 (pt) | 2004-03-10 | 2014-09-16 | Monsanto Technology Llc | Composições de concentrado herbicida compreendendo glifosato e herbicida auxina |
US20060171909A1 (en) * | 2005-02-03 | 2006-08-03 | The Procter & Gamble Company | Cosmetic compositions comprising colorants with low free dye |
US20070234789A1 (en) * | 2006-04-05 | 2007-10-11 | Gerard Glasbergen | Fluid distribution determination and optimization with real time temperature measurement |
WO2008091538A1 (en) * | 2007-01-22 | 2008-07-31 | Dow Agrosciences Llc | Enhanced nitrification inhibitor composition |
US8741805B2 (en) * | 2007-01-22 | 2014-06-03 | Dow Agrosciences, Llc. | Enhanced nitrification inhibitor composition |
US20100083873A1 (en) * | 2008-10-06 | 2010-04-08 | Southwest Research Institute | Encapsulation Of Active Agents For On-Demand Release |
WO2010053940A1 (en) * | 2008-11-07 | 2010-05-14 | The Procter & Gamble Company | Benefit agent containing delivery particle |
AU2010213530B2 (en) * | 2009-02-13 | 2015-09-03 | Monsanto Technology Llc | Encapsulation of herbicides to reduce crop injury |
FR2943219B1 (fr) * | 2009-03-20 | 2012-05-18 | Polytek Innovations | Produit a usage agricole et son procede de fabrication |
PL2408298T3 (pl) * | 2009-03-20 | 2016-12-30 | Sposób traktowania roślin uprawnych kapsułkowanym pestycydem | |
US20120142532A1 (en) | 2009-08-10 | 2012-06-07 | Monsanto Technology Llc | Low volatility auxin herbicide formulations |
EP2399667B1 (en) * | 2010-06-25 | 2017-03-08 | Cognis IP Management GmbH | Process for producing microcapsules |
WO2012024524A1 (en) | 2010-08-18 | 2012-02-23 | Monsanto Technology Llc | Early applications of encapsulated acetamides for reduced injury in crops |
US9333454B2 (en) | 2011-01-21 | 2016-05-10 | International Business Machines Corporation | Silicone-based chemical filter and silicone-based chemical bath for removing sulfur contaminants |
US8900491B2 (en) | 2011-05-06 | 2014-12-02 | International Business Machines Corporation | Flame retardant filler |
US9186641B2 (en) | 2011-08-05 | 2015-11-17 | International Business Machines Corporation | Microcapsules adapted to rupture in a magnetic field to enable easy removal of one substrate from another for enhanced reworkability |
EP2744329A1 (en) * | 2011-08-19 | 2014-06-25 | Basf Se | Formulations for paddy rice fields |
BR122019001044B1 (pt) | 2011-10-26 | 2019-08-27 | Monsanto Technology Llc | sais herbicidas de auxina, mistura de aplicação herbicida compreendendo os mesmos para uso na eliminação e controle do crescimento de plantas indesejadas, bem como métodos de controle de plantas indesejadas e de plantas suscetíveis ao herbicida de auxina |
US8741804B2 (en) * | 2011-10-28 | 2014-06-03 | International Business Machines Corporation | Microcapsules adapted to rupture in a magnetic field |
CN102428952B (zh) * | 2011-11-17 | 2013-06-26 | 广东中迅农科股份有限公司 | 一种用于防治小麦全蚀病的增效杀菌组合物 |
JP2013151472A (ja) * | 2011-12-27 | 2013-08-08 | Sumitomo Chemical Co Ltd | 殺菌活性成分を含有するマイクロカプセル |
PL2779831T3 (pl) * | 2011-12-27 | 2018-11-30 | Dow Global Technologies Llc | Mikrokapsułki |
CN102550552A (zh) * | 2012-01-13 | 2012-07-11 | 广东中迅农科股份有限公司 | 氟硅唑微胶囊悬浮剂及其制备方法 |
CN103238621A (zh) * | 2012-02-04 | 2013-08-14 | 陕西美邦农药有限公司 | 一种含硅噻菌胺与三唑类化合物的杀菌组合物 |
CN102599165A (zh) * | 2012-02-21 | 2012-07-25 | 广东中迅农科股份有限公司 | 嘧菌酯微胶囊悬浮剂及其制备方法 |
CN102630686A (zh) * | 2012-04-11 | 2012-08-15 | 苏州佳辉化工有限公司 | 一种含野麦畏的微胶囊悬浮剂及其制备方法 |
US10736322B2 (en) | 2012-06-04 | 2020-08-11 | Monsanto Technology Llc | Aqueous concentrated herbicidal compositions containing glyphosate salts and dicamba salts |
US9716055B2 (en) | 2012-06-13 | 2017-07-25 | International Business Machines Corporation | Thermal interface material (TIM) with thermally conductive integrated release layer |
CN103120177A (zh) * | 2013-02-06 | 2013-05-29 | 吉林省八达农药有限公司 | 一种含有硅噻菌胺与三唑类杀菌剂的农用杀菌剂组合物 |
CN105072912A (zh) | 2013-02-27 | 2015-11-18 | 孟山都技术公司 | 用于具有改进的挥发性的麦草畏桶混合物的草甘膦组合物 |
CN103300052A (zh) * | 2013-07-10 | 2013-09-18 | 河北博嘉农业有限公司 | 一种含有硅噻菌胺的小麦种子处理剂组合物 |
WO2015113015A1 (en) | 2014-01-27 | 2015-07-30 | Monsanto Technology Llc | Aqueous herbicidal concentrates |
US9862652B2 (en) | 2014-05-02 | 2018-01-09 | Dow Agrosciences Llc | Microencapsulated nitrification inhibitor composition |
HUE046882T2 (hu) * | 2015-06-19 | 2020-03-30 | Basf Se | Tetrametil-xililén-diizocianátból, cikloalifás-diizocianátból és alifás diaminból készült héjjal rendelkezõ peszticid mikrokapszulák |
WO2016202659A1 (en) * | 2015-06-19 | 2016-12-22 | Basf Se | Pendimethanlin microcapsules with a shell made of tetramethylxylylene diisocyanate and a pol-yamine with at least three amine groups |
ES2841373T3 (es) * | 2015-08-17 | 2021-07-08 | Obshchestvo S Ogranitchennoy Otvetstvennostyu Fungi Pak | Preparación biológicamente activa que comprende microcontenedores para proteger plantas contra plagas y método para su producción |
AR112100A1 (es) | 2017-06-13 | 2019-09-18 | Monsanto Technology Llc | Herbicidas microencapsulados |
BR102019014454A2 (pt) * | 2018-07-13 | 2020-02-04 | Upl Ltd | composição compreendendo mistura eutética de fungicida boscalide e estrobilurina |
CN113573584A (zh) | 2019-01-30 | 2021-10-29 | 孟山都技术有限公司 | 微胶囊化乙酰胺除草剂 |
CN109645024A (zh) * | 2019-01-31 | 2019-04-19 | 安徽舒州农业科技有限责任公司 | 一种含硅噻菌胺和粉唑醇的杀菌组合物 |
CN111972422B (zh) * | 2019-05-21 | 2022-10-25 | 江苏龙灯化学有限公司 | 一种含有微胶囊的除草组合物及其制备方法和用途 |
CN112029510B (zh) * | 2020-10-15 | 2021-09-17 | 丽水学院 | 一种复合型土壤改良剂及其制备方法和应用 |
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US3516941A (en) | 1966-07-25 | 1970-06-23 | Minnesota Mining & Mfg | Microcapsules and process of making |
US3516846A (en) | 1969-11-18 | 1970-06-23 | Minnesota Mining & Mfg | Microcapsule-containing paper |
US4285720A (en) | 1972-03-15 | 1981-08-25 | Stauffer Chemical Company | Encapsulation process and capsules produced thereby |
DK253779A (da) | 1978-08-03 | 1980-02-04 | Du Pont | Insecticidt middel og fremgangsmaade til fremstilling deraf |
US4280833A (en) * | 1979-03-26 | 1981-07-28 | Monsanto Company | Encapsulation by interfacial polycondensation, and aqueous herbicidal composition containing microcapsules produced thereby |
US4956129A (en) | 1984-03-30 | 1990-09-11 | Ici Americas Inc. | Microencapsulation process |
US4599271A (en) | 1983-06-09 | 1986-07-08 | Moore Business Forms, Inc. | Microencapsulation of polyisocyanates by interchange of multiple |
US4643764A (en) | 1984-01-09 | 1987-02-17 | Stauffer Chemical Company | Multiple types of microcapsules and their production |
US4640709A (en) | 1984-06-12 | 1987-02-03 | Monsanto Company | High concentration encapsulation by interfacial polycondensation |
ATE77916T1 (de) * | 1985-09-13 | 1992-07-15 | Ciba Geigy Ag | Verfahren zur herstellung von mikrokapseln. |
FR2591124B1 (fr) | 1985-12-10 | 1988-02-12 | Rhone Poulenc Spec Chim | Procede de microencapsulation par polyaddition-interfaciale. |
US4681806A (en) | 1986-02-13 | 1987-07-21 | Minnesota Mining And Manufacturing Company | Particles containing releasable fill material and method of making same |
HU208218B (en) * | 1986-07-09 | 1993-09-28 | Monsanto Co | Pesticidal granulated compositions dispersible in freely flowing water and process for producing same |
ES2042794T3 (es) | 1987-03-06 | 1993-12-16 | Ciba Geigy Ag | Composiciones herbicidas. |
JPH0818937B2 (ja) | 1987-07-06 | 1996-02-28 | 住友化学工業株式会社 | 農園芸用有機燐系殺虫組成物 |
GB8827029D0 (en) | 1988-11-18 | 1988-12-21 | Ici Plc | Insecticidal compositions |
US5306712A (en) | 1991-10-09 | 1994-04-26 | Sanyo Company, Limited | Fungicidal silicon-containing compounds and their agrochemical and medicinal uses |
HU219131B (hu) | 1991-10-18 | 2001-02-28 | Monsanto Co. | Módszer és fungicid készítmény növények torsgombabetegségének gátlására és a hatóanyagok |
ATE156728T1 (de) | 1992-01-03 | 1997-08-15 | Ciba Geigy Ag | Suspension von mikrokapseln und verfahren zu ihrer herstellung |
HRP921338B1 (en) | 1992-10-02 | 2002-04-30 | Monsanto Co | Fungicides for the control of take-all disease of plants |
HU221040B1 (hu) | 1993-04-06 | 2002-07-29 | Monsanto Co. | Eljárás és fungicid készítmény növények torsgombabetegségnek leküzdésére és a hatóanyagok |
US5482974A (en) | 1994-03-08 | 1996-01-09 | Monsanto Company | Selected fungicides for the control of take-all disease of plants |
US5486621A (en) | 1994-12-15 | 1996-01-23 | Monsanto Company | Fungicides for the control of take-all disease of plants |
US5925464A (en) * | 1995-01-19 | 1999-07-20 | Dow Agrosciences Llc | Microencapsulation process and product |
ZA974359B (en) | 1996-05-23 | 1998-05-12 | Zeneca Ltd | Microencapsulated compositions. |
US5925595A (en) * | 1997-09-05 | 1999-07-20 | Monsanto Company | Microcapsules with readily adjustable release rates |
EP1023283B1 (en) | 1997-10-14 | 2003-01-29 | Monsanto Technology LLC | Synthesis of 3-carbomethoxy-4,5-dimethylthiophene |
GB9824331D0 (en) | 1998-11-06 | 1998-12-30 | Novartis Ag | Organic compounds |
DE19939841A1 (de) * | 1998-11-20 | 2000-05-25 | Bayer Ag | Fungizide Wirkstoffkombinationen |
US7687434B2 (en) * | 2000-12-22 | 2010-03-30 | Monsanto Technology, Llc | Method of improving yield and vigor of plants |
US6992047B2 (en) * | 2001-04-11 | 2006-01-31 | Monsanto Technology Llc | Method of microencapsulating an agricultural active having a high melting point and uses for such materials |
EP1569513A1 (en) * | 2002-12-13 | 2005-09-07 | Monsanto Technology LLC | Microcapsules with amine adjusted release rates |
-
2002
- 2002-04-03 US US10/115,765 patent/US6992047B2/en not_active Expired - Fee Related
- 2002-04-04 CA CA002442585A patent/CA2442585A1/en not_active Abandoned
- 2002-04-04 ES ES02761998T patent/ES2268073T3/es not_active Expired - Lifetime
- 2002-04-04 BR BR0208838-0A patent/BR0208838A/pt not_active IP Right Cessation
- 2002-04-04 AT AT02761998T patent/ATE330470T1/de not_active IP Right Cessation
- 2002-04-04 CN CNA200710137081XA patent/CN101099460A/zh active Pending
- 2002-04-04 WO PCT/US2002/010551 patent/WO2002082901A1/en active IP Right Grant
- 2002-04-04 UA UA20031110117A patent/UA75401C2/uk unknown
- 2002-04-04 EP EP02761998A patent/EP1377161B1/en not_active Expired - Lifetime
- 2002-04-04 PL PL02367398A patent/PL367398A1/xx unknown
- 2002-04-04 MX MXPA03009247A patent/MXPA03009247A/es active IP Right Grant
- 2002-04-04 CN CNB028081846A patent/CN100337541C/zh not_active Expired - Fee Related
- 2002-04-04 DE DE60212603T patent/DE60212603T2/de not_active Expired - Lifetime
- 2002-04-04 AU AU2002307105A patent/AU2002307105B2/en not_active Ceased
-
2003
- 2003-09-12 ZA ZA200307178A patent/ZA200307178B/en unknown
-
2005
- 2005-04-25 US US11/113,857 patent/US20050208089A1/en not_active Abandoned
-
2008
- 2008-05-05 US US12/151,267 patent/US20080242548A1/en not_active Abandoned
Also Published As
Publication number | Publication date |
---|---|
CN101099460A (zh) | 2008-01-09 |
UA75401C2 (en) | 2006-04-17 |
ES2268073T3 (es) | 2007-03-16 |
EP1377161B1 (en) | 2006-06-21 |
CA2442585A1 (en) | 2002-10-24 |
CN1501771A (zh) | 2004-06-02 |
BR0208838A (pt) | 2004-03-09 |
AU2002307105B2 (en) | 2008-01-31 |
DE60212603D1 (de) | 2006-08-03 |
ATE330470T1 (de) | 2006-07-15 |
PL367398A1 (en) | 2005-02-21 |
US20080242548A1 (en) | 2008-10-02 |
CN100337541C (zh) | 2007-09-19 |
EP1377161A1 (en) | 2004-01-07 |
DE60212603T2 (de) | 2007-05-24 |
US20030022791A1 (en) | 2003-01-30 |
US20050208089A1 (en) | 2005-09-22 |
MXPA03009247A (es) | 2004-01-29 |
WO2002082901A1 (en) | 2002-10-24 |
US6992047B2 (en) | 2006-01-31 |
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