UA75401C2 - Method of producing microcapsulated form of high-melting material and a form of an agricultural active material produced by this method - Google Patents
Method of producing microcapsulated form of high-melting material and a form of an agricultural active material produced by this method Download PDFInfo
- Publication number
- UA75401C2 UA75401C2 UA20031110117A UA20031110117A UA75401C2 UA 75401 C2 UA75401 C2 UA 75401C2 UA 20031110117 A UA20031110117 A UA 20031110117A UA 20031110117 A UA20031110117 A UA 20031110117A UA 75401 C2 UA75401 C2 UA 75401C2
- Authority
- UA
- Ukraine
- Prior art keywords
- alkyl
- alkylthio
- halo
- optionally substituted
- dialkylamino
- Prior art date
Links
- 238000002844 melting Methods 0.000 title claims abstract description 125
- 238000000034 method Methods 0.000 title claims abstract description 96
- 239000011149 active material Substances 0.000 title claims abstract description 14
- 239000000463 material Substances 0.000 title claims description 62
- 239000003094 microcapsule Substances 0.000 claims abstract description 145
- 239000000203 mixture Substances 0.000 claims abstract description 109
- 230000008018 melting Effects 0.000 claims abstract description 99
- 239000007788 liquid Substances 0.000 claims abstract description 56
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 42
- 238000013270 controlled release Methods 0.000 claims abstract description 29
- 230000007613 environmental effect Effects 0.000 claims abstract description 14
- -1 cyano, amino, nitro, thiocyanato, isothiocyanato, trimethylsilyl Chemical group 0.000 claims description 310
- 239000013543 active substance Substances 0.000 claims description 113
- 125000004414 alkyl thio group Chemical group 0.000 claims description 65
- MXMXHPPIGKYTAR-UHFFFAOYSA-N silthiofam Chemical group CC=1SC([Si](C)(C)C)=C(C(=O)NCC=C)C=1C MXMXHPPIGKYTAR-UHFFFAOYSA-N 0.000 claims description 64
- 125000005843 halogen group Chemical group 0.000 claims description 58
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 49
- 239000000243 solution Substances 0.000 claims description 49
- 229920002396 Polyurea Polymers 0.000 claims description 45
- 125000003282 alkyl amino group Chemical group 0.000 claims description 43
- 125000003342 alkenyl group Chemical group 0.000 claims description 41
- 125000003545 alkoxy group Chemical group 0.000 claims description 41
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 41
- 125000001188 haloalkyl group Chemical group 0.000 claims description 37
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 claims description 35
- 125000000304 alkynyl group Chemical group 0.000 claims description 35
- 125000000217 alkyl group Chemical group 0.000 claims description 30
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 29
- 239000005835 Silthiofam Substances 0.000 claims description 26
- 150000001875 compounds Chemical class 0.000 claims description 26
- 229910052736 halogen Inorganic materials 0.000 claims description 26
- 150000002367 halogens Chemical group 0.000 claims description 26
- 229920000768 polyamine Polymers 0.000 claims description 26
- 150000001412 amines Chemical group 0.000 claims description 25
- 230000015572 biosynthetic process Effects 0.000 claims description 25
- 229920001228 polyisocyanate Polymers 0.000 claims description 24
- 239000005056 polyisocyanate Substances 0.000 claims description 24
- 239000002904 solvent Substances 0.000 claims description 23
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 22
- 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 21
- 241000196324 Embryophyta Species 0.000 claims description 21
- 239000005839 Tebuconazole Substances 0.000 claims description 21
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 20
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 19
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 19
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 19
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 18
- 229910052799 carbon Inorganic materials 0.000 claims description 18
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 18
- 239000000374 eutectic mixture Substances 0.000 claims description 18
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 17
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 17
- 238000002156 mixing Methods 0.000 claims description 17
- 238000006116 polymerization reaction Methods 0.000 claims description 17
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 16
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 16
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 14
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 14
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 14
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 14
- 230000000994 depressogenic effect Effects 0.000 claims description 14
- 125000004473 dialkylaminocarbonyl group Chemical group 0.000 claims description 14
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 14
- 238000004519 manufacturing process Methods 0.000 claims description 14
- 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 13
- 125000003118 aryl group Chemical group 0.000 claims description 13
- 150000003839 salts Chemical class 0.000 claims description 13
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 12
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 12
- 239000003638 chemical reducing agent Substances 0.000 claims description 12
- 239000004480 active ingredient Substances 0.000 claims description 11
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 11
- AGGKEGLBGGJEBZ-UHFFFAOYSA-N tetramethylenedisulfotetramine Chemical compound C1N(S2(=O)=O)CN3S(=O)(=O)N1CN2C3 AGGKEGLBGGJEBZ-UHFFFAOYSA-N 0.000 claims description 11
- 238000012695 Interfacial polymerization Methods 0.000 claims description 10
- 235000021307 Triticum Nutrition 0.000 claims description 10
- 239000004009 herbicide Substances 0.000 claims description 10
- 125000005442 diisocyanate group Chemical group 0.000 claims description 9
- 239000000417 fungicide Substances 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
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 9
- 229930192474 thiophene Natural products 0.000 claims description 9
- 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 8
- 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 8
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims description 8
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 8
- 125000002541 furyl group Chemical group 0.000 claims description 8
- 230000002363 herbicidal effect Effects 0.000 claims description 8
- 239000000575 pesticide Substances 0.000 claims description 8
- 125000001544 thienyl group Chemical group 0.000 claims description 8
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 7
- 230000000855 fungicidal effect Effects 0.000 claims description 7
- 125000000262 haloalkenyl group Chemical group 0.000 claims description 7
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 claims description 7
- 239000005807 Metalaxyl Substances 0.000 claims description 6
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 6
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 6
- 239000007983 Tris buffer Substances 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
- 238000009472 formulation Methods 0.000 claims description 6
- 238000010438 heat treatment Methods 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical compound C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 claims description 6
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 6
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 5
- 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 5
- 239000005746 Carboxin Substances 0.000 claims description 5
- 239000005760 Difenoconazole Substances 0.000 claims description 5
- 239000005781 Fludioxonil Substances 0.000 claims description 5
- 239000005785 Fluquinconazole Substances 0.000 claims description 5
- 239000005840 Tetraconazole Substances 0.000 claims description 5
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 claims description 5
- GYSSRZJIHXQEHQ-UHFFFAOYSA-N carboxin Chemical compound S1CCOC(C)=C1C(=O)NC1=CC=CC=C1 GYSSRZJIHXQEHQ-UHFFFAOYSA-N 0.000 claims description 5
- 235000013339 cereals Nutrition 0.000 claims description 5
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 5
- 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 5
- MUJOIMFVNIBMKC-UHFFFAOYSA-N fludioxonil Chemical compound C=12OC(F)(F)OC2=CC=CC=1C1=CNC=C1C#N MUJOIMFVNIBMKC-UHFFFAOYSA-N 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
- 125000000623 heterocyclic group Chemical group 0.000 claims description 5
- 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 5
- 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 4
- 239000005745 Captan Substances 0.000 claims description 4
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 239000005843 Thiram Substances 0.000 claims description 4
- 229910052796 boron Inorganic materials 0.000 claims description 4
- 229940117949 captan Drugs 0.000 claims description 4
- 239000001257 hydrogen 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
- 229920001451 polypropylene glycol Polymers 0.000 claims description 4
- 150000003335 secondary amines Chemical group 0.000 claims description 4
- KUAZQDVKQLNFPE-UHFFFAOYSA-N thiram Chemical compound CN(C)C(=S)SSC(=S)N(C)C KUAZQDVKQLNFPE-UHFFFAOYSA-N 0.000 claims description 4
- 229960002447 thiram Drugs 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
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 claims description 3
- 240000004658 Medicago sativa Species 0.000 claims description 3
- 235000017587 Medicago sativa ssp. sativa Nutrition 0.000 claims description 3
- 240000004713 Pisum sativum Species 0.000 claims description 3
- 235000010582 Pisum sativum Nutrition 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
- 230000000844 anti-bacterial effect Effects 0.000 claims description 3
- 239000003899 bactericide agent Substances 0.000 claims description 3
- 150000004985 diamines Chemical class 0.000 claims description 3
- 239000002917 insecticide Substances 0.000 claims description 3
- 239000003750 molluscacide Substances 0.000 claims description 3
- 230000002013 molluscicidal effect Effects 0.000 claims description 3
- 239000005645 nematicide Substances 0.000 claims description 3
- FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical compound NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 claims description 3
- KELIOZMTDOSCMM-UHFFFAOYSA-N 2,3,3a,4-tetrahydro-1-benzothiophene Chemical compound C1C=CC=C2SCCC21 KELIOZMTDOSCMM-UHFFFAOYSA-N 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
- 244000020518 Carthamus tinctorius Species 0.000 claims description 2
- 235000003255 Carthamus tinctorius Nutrition 0.000 claims description 2
- 229920000742 Cotton Polymers 0.000 claims description 2
- 244000299507 Gossypium hirsutum Species 0.000 claims description 2
- 244000020551 Helianthus annuus Species 0.000 claims description 2
- 235000003222 Helianthus annuus Nutrition 0.000 claims description 2
- 240000005979 Hordeum vulgare Species 0.000 claims description 2
- 235000007340 Hordeum vulgare Nutrition 0.000 claims description 2
- 244000061176 Nicotiana tabacum Species 0.000 claims description 2
- 235000002637 Nicotiana tabacum Nutrition 0.000 claims description 2
- 240000007594 Oryza sativa Species 0.000 claims description 2
- 235000007164 Oryza sativa Nutrition 0.000 claims description 2
- 244000046052 Phaseolus vulgaris Species 0.000 claims description 2
- 235000010627 Phaseolus vulgaris Nutrition 0.000 claims description 2
- 240000000111 Saccharum officinarum Species 0.000 claims description 2
- 235000007201 Saccharum officinarum Nutrition 0.000 claims description 2
- 235000007238 Secale cereale Nutrition 0.000 claims description 2
- 244000082988 Secale cereale Species 0.000 claims description 2
- 235000011684 Sorghum saccharatum Nutrition 0.000 claims description 2
- 235000021536 Sugar beet Nutrition 0.000 claims description 2
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 2
- 150000008052 alkyl sulfonates Chemical class 0.000 claims description 2
- 125000004465 cycloalkenyloxy group Chemical group 0.000 claims description 2
- 125000004692 haloalkylcarbonyl group Chemical group 0.000 claims description 2
- 230000001069 nematicidal effect Effects 0.000 claims description 2
- 150000002825 nitriles Chemical class 0.000 claims description 2
- 239000004417 polycarbonate Substances 0.000 claims description 2
- 229920000515 polycarbonate Polymers 0.000 claims description 2
- 229920000921 polyethylene adipate Polymers 0.000 claims description 2
- 150000003141 primary amines Chemical group 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 235000009566 rice Nutrition 0.000 claims description 2
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims description 2
- 229940035289 tobi Drugs 0.000 claims description 2
- NLVFBUXFDBBNBW-PBSUHMDJSA-N tobramycin Chemical compound N[C@@H]1C[C@H](O)[C@@H](CN)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O[C@@H]2[C@@H]([C@@H](N)[C@H](O)[C@@H](CO)O2)O)[C@H](N)C[C@@H]1N NLVFBUXFDBBNBW-PBSUHMDJSA-N 0.000 claims description 2
- 235000013311 vegetables Nutrition 0.000 claims description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims 2
- AVJPROTYKYNVCI-UHFFFAOYSA-N 1-benzothiophene;thiophene Chemical group C=1C=CSC=1.C1=CC=C2SC=CC2=C1 AVJPROTYKYNVCI-UHFFFAOYSA-N 0.000 claims 1
- 239000002202 Polyethylene glycol Substances 0.000 claims 1
- 240000006394 Sorghum bicolor Species 0.000 claims 1
- 244000098338 Triticum aestivum Species 0.000 claims 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims 1
- 229920001223 polyethylene glycol Polymers 0.000 claims 1
- 230000001902 propagating effect Effects 0.000 claims 1
- 230000001850 reproductive effect Effects 0.000 claims 1
- 239000003849 aromatic solvent Substances 0.000 abstract description 11
- 239000011162 core material Substances 0.000 description 100
- 239000011257 shell material Substances 0.000 description 80
- 239000000126 substance Substances 0.000 description 36
- 239000002245 particle Substances 0.000 description 28
- 239000012948 isocyanate Substances 0.000 description 23
- 150000002513 isocyanates Chemical class 0.000 description 22
- 239000007787 solid Substances 0.000 description 18
- 238000000576 coating method Methods 0.000 description 16
- 239000011248 coating agent Substances 0.000 description 12
- 238000005538 encapsulation Methods 0.000 description 12
- 239000003112 inhibitor Substances 0.000 description 11
- 239000007864 aqueous solution Substances 0.000 description 10
- 239000002775 capsule Substances 0.000 description 10
- 239000000839 emulsion Substances 0.000 description 10
- 241000209140 Triticum Species 0.000 description 9
- 230000000694 effects Effects 0.000 description 8
- 239000012074 organic phase Substances 0.000 description 8
- 238000010521 absorption reaction Methods 0.000 description 7
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 description 7
- 239000002689 soil Substances 0.000 description 7
- 239000000725 suspension Substances 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 6
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 6
- 229930195733 hydrocarbon Natural products 0.000 description 6
- 150000002430 hydrocarbons Chemical class 0.000 description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
- 230000016507 interphase Effects 0.000 description 6
- 239000012071 phase Substances 0.000 description 6
- 229920000642 polymer Polymers 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 6
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 5
- 125000003277 amino group Chemical group 0.000 description 5
- 239000008346 aqueous phase Substances 0.000 description 5
- 230000003247 decreasing effect Effects 0.000 description 5
- 239000011159 matrix material Substances 0.000 description 5
- 239000004094 surface-active agent Substances 0.000 description 5
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
- 125000000440 benzylamino group Chemical group [H]N(*)C([H])([H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 4
- 230000005496 eutectics Effects 0.000 description 4
- 125000001475 halogen functional group Chemical group 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 230000008569 process Effects 0.000 description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 3
- 150000001408 amides Chemical class 0.000 description 3
- 239000012298 atmosphere Substances 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 239000000975 dye Substances 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 150000002170 ethers Chemical class 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 125000000524 functional group Chemical group 0.000 description 3
- 150000002440 hydroxy compounds Chemical class 0.000 description 3
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 3
- 238000001000 micrograph Methods 0.000 description 3
- 239000000178 monomer Substances 0.000 description 3
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- 125000006079 1,1,2-trimethyl-2-propenyl group Chemical group 0.000 description 2
- 125000006059 1,1-dimethyl-2-butenyl group Chemical group 0.000 description 2
- 125000006033 1,1-dimethyl-2-propenyl group Chemical group 0.000 description 2
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
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- XWPZUHJBOLQNMN-UHFFFAOYSA-N metconazole Chemical compound C1=NC=NN1CC1(O)C(C)(C)CCC1CC1=CC=C(Cl)C=C1 XWPZUHJBOLQNMN-UHFFFAOYSA-N 0.000 description 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
- CJPQIRJHIZUAQP-UHFFFAOYSA-N methyl N-(2,6-dimethylphenyl)-N-(phenylacetyl)alaninate Chemical compound CC=1C=CC=C(C)C=1N(C(C)C(=O)OC)C(=O)CC1=CC=CC=C1 CJPQIRJHIZUAQP-UHFFFAOYSA-N 0.000 description 1
- CIEXPHRYOLIQQD-UHFFFAOYSA-N methyl N-(2,6-dimethylphenyl)-N-2-furoylalaninate Chemical compound CC=1C=CC=C(C)C=1N(C(C)C(=O)OC)C(=O)C1=CC=CO1 CIEXPHRYOLIQQD-UHFFFAOYSA-N 0.000 description 1
- GDOPTJXRTPNYNR-UHFFFAOYSA-N methyl-cyclopentane Natural products CC1CCCC1 GDOPTJXRTPNYNR-UHFFFAOYSA-N 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 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
- 239000011859 microparticle Substances 0.000 description 1
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- GLBKTDWFAKSVGS-UHFFFAOYSA-N n-diethoxyphosphorylethanamine Chemical group CCNP(=O)(OCC)OCC GLBKTDWFAKSVGS-UHFFFAOYSA-N 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
- 150000002826 nitrites Chemical class 0.000 description 1
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 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
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 238000000399 optical microscopy Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000008520 organization Effects 0.000 description 1
- UNAHYJYOSSSJHH-UHFFFAOYSA-N oryzalin Chemical compound CCCN(CCC)C1=C([N+]([O-])=O)C=C(S(N)(=O)=O)C=C1[N+]([O-])=O UNAHYJYOSSSJHH-UHFFFAOYSA-N 0.000 description 1
- 108010049640 osmotic shock released antigen Proteins 0.000 description 1
- UWVQIROCRJWDKL-UHFFFAOYSA-N oxadixyl Chemical compound CC=1C=CC=C(C)C=1N(C(=O)COC)N1CCOC1=O UWVQIROCRJWDKL-UHFFFAOYSA-N 0.000 description 1
- IOXAXYHXMLCCJJ-UHFFFAOYSA-N oxetan-3-yl 2-[(4,6-dimethylpyrimidin-2-yl)carbamoylsulfamoyl]benzoate Chemical compound CC1=CC(C)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)C(=O)OC2COC2)=N1 IOXAXYHXMLCCJJ-UHFFFAOYSA-N 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
- 235000020232 peanut Nutrition 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
- IDOWTHOLJBTAFI-UHFFFAOYSA-N phenmedipham Chemical compound COC(=O)NC1=CC=CC(OC(=O)NC=2C=C(C)C=CC=2)=C1 IDOWTHOLJBTAFI-UHFFFAOYSA-N 0.000 description 1
- LCPDWSOZIOUXRV-UHFFFAOYSA-N phenoxyacetic acid Chemical class OC(=O)COC1=CC=CC=C1 LCPDWSOZIOUXRV-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
- 231100000208 phytotoxic Toxicity 0.000 description 1
- 230000000885 phytotoxic effect Effects 0.000 description 1
- NQQVFXUMIDALNH-UHFFFAOYSA-N picloram Chemical compound NC1=C(Cl)C(Cl)=NC(C(O)=O)=C1Cl NQQVFXUMIDALNH-UHFFFAOYSA-N 0.000 description 1
- SIOXPEMLGUPBBT-UHFFFAOYSA-N picolinic acid Chemical class OC(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-N 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920000172 poly(styrenesulfonic acid) Polymers 0.000 description 1
- ODGAOXROABLFNM-UHFFFAOYSA-N polynoxylin Chemical compound O=C.NC(N)=O ODGAOXROABLFNM-UHFFFAOYSA-N 0.000 description 1
- 229940005642 polystyrene sulfonic acid Drugs 0.000 description 1
- 239000004810 polytetrafluoroethylene Substances 0.000 description 1
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- TVLSRXXIMLFWEO-UHFFFAOYSA-N prochloraz Chemical compound C1=CN=CN1C(=O)N(CCC)CCOC1=C(Cl)C=C(Cl)C=C1Cl TVLSRXXIMLFWEO-UHFFFAOYSA-N 0.000 description 1
- ISEUFVQQFVOBCY-UHFFFAOYSA-N prometon Chemical compound COC1=NC(NC(C)C)=NC(NC(C)C)=N1 ISEUFVQQFVOBCY-UHFFFAOYSA-N 0.000 description 1
- MFOUDYKPLGXPGO-UHFFFAOYSA-N propachlor Chemical compound ClCC(=O)N(C(C)C)C1=CC=CC=C1 MFOUDYKPLGXPGO-UHFFFAOYSA-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
- STJLVHWMYQXCPB-UHFFFAOYSA-N propiconazole Chemical compound O1C(CCC)COC1(C=1C(=CC(Cl)=CC=1)Cl)CN1N=CN=C1 STJLVHWMYQXCPB-UHFFFAOYSA-N 0.000 description 1
- AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 description 1
- PHNUZKMIPFFYSO-UHFFFAOYSA-N propyzamide Chemical compound C#CC(C)(C)NC(=O)C1=CC(Cl)=CC(Cl)=C1 PHNUZKMIPFFYSO-UHFFFAOYSA-N 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000001878 scanning electron micrograph Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- ODCWYMIRDDJXKW-UHFFFAOYSA-N simazine Chemical compound CCNC1=NC(Cl)=NC(NCC)=N1 ODCWYMIRDDJXKW-UHFFFAOYSA-N 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- XOTREVBPKJHQEX-UHFFFAOYSA-M sodium;2-(3,3,6,6-tetramethyl-1,8-dioxo-9-phenyl-4,5,7,9-tetrahydro-2h-acridin-10-yl)acetate Chemical compound [Na+].C1C(C)(C)CC(=O)C2=C1N(CC([O-])=O)C(CC(C)(C)CC1=O)=C1C2C1=CC=CC=C1 XOTREVBPKJHQEX-UHFFFAOYSA-M 0.000 description 1
- JUNDBKFAZXZKRA-MAFYXNADSA-M sodium;2-[(e)-n-[(3,5-difluorophenyl)carbamoylamino]-c-methylcarbonimidoyl]pyridine-3-carboxylate Chemical compound [Na+].N=1C=CC=C(C([O-])=O)C=1C(/C)=N/NC(=O)NC1=CC(F)=CC(F)=C1 JUNDBKFAZXZKRA-MAFYXNADSA-M 0.000 description 1
- 239000002195 soluble material Substances 0.000 description 1
- PUYXTUJWRLOUCW-UHFFFAOYSA-N spiroxamine Chemical compound O1C(CN(CC)CCC)COC11CCC(C(C)(C)C)CC1 PUYXTUJWRLOUCW-UHFFFAOYSA-N 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- FZMKKCQHDROFNI-UHFFFAOYSA-N sulfometuron Chemical compound CC1=CC(C)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)C(O)=O)=N1 FZMKKCQHDROFNI-UHFFFAOYSA-N 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- LOQQVLXUKHKNIA-UHFFFAOYSA-N thifensulfuron Chemical compound COC1=NC(C)=NC(NC(=O)NS(=O)(=O)C2=C(SC=C2)C(O)=O)=N1 LOQQVLXUKHKNIA-UHFFFAOYSA-N 0.000 description 1
- DQFPEYARZIQXRM-LTGZKZEYSA-N tralkoxydim Chemical compound C1C(=O)C(C(/CC)=N/OCC)=C(O)CC1C1=C(C)C=C(C)C=C1C DQFPEYARZIQXRM-LTGZKZEYSA-N 0.000 description 1
- 229960002622 triacetin Drugs 0.000 description 1
- BAZVSMNPJJMILC-UHFFFAOYSA-N triadimenol Chemical compound C1=NC=NN1C(C(O)C(C)(C)C)OC1=CC=C(Cl)C=C1 BAZVSMNPJJMILC-UHFFFAOYSA-N 0.000 description 1
- XOPFESVZMSQIKC-UHFFFAOYSA-N triasulfuron Chemical compound COC1=NC(C)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)OCCCl)=N1 XOPFESVZMSQIKC-UHFFFAOYSA-N 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- IQGKIPDJXCAMSM-UHFFFAOYSA-N triazoxide Chemical compound N=1C2=CC=C(Cl)C=C2[N+]([O-])=NC=1N1C=CN=C1 IQGKIPDJXCAMSM-UHFFFAOYSA-N 0.000 description 1
- BQZXUHDXIARLEO-UHFFFAOYSA-N tribenuron Chemical compound COC1=NC(C)=NC(N(C)C(=O)NS(=O)(=O)C=2C(=CC=CC=2)C(O)=O)=N1 BQZXUHDXIARLEO-UHFFFAOYSA-N 0.000 description 1
- REEQLXCGVXDJSQ-UHFFFAOYSA-N trichlopyr Chemical compound OC(=O)COC1=NC(Cl)=C(Cl)C=C1Cl REEQLXCGVXDJSQ-UHFFFAOYSA-N 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 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
- AKTQJCBOGPBERP-UHFFFAOYSA-N triflusulfuron Chemical compound FC(F)(F)COC1=NC(N(C)C)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2C)C(O)=O)=N1 AKTQJCBOGPBERP-UHFFFAOYSA-N 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 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
- 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 (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US28305301P | 2001-04-11 | 2001-04-11 | |
| PCT/US2002/010551 WO2002082901A1 (en) | 2001-04-11 | 2002-04-04 | Microencapsulating of an agricultural active having a high melting point |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| UA75401C2 true UA75401C2 (en) | 2006-04-17 |
Family
ID=23084281
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| UA20031110117A UA75401C2 (en) | 2001-04-11 | 2002-04-04 | Method of producing microcapsulated form of high-melting material and a form of an agricultural active material produced by this method |
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) |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| 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 |
| ZA200307178B (en) | 2005-02-14 |
| US20050208089A1 (en) | 2005-09-22 |
| MXPA03009247A (es) | 2004-01-29 |
| WO2002082901A1 (en) | 2002-10-24 |
| US6992047B2 (en) | 2006-01-31 |
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