BR0110978B1 - Concentrados e formulações de glifosato - Google Patents
Concentrados e formulações de glifosato Download PDFInfo
- Publication number
- BR0110978B1 BR0110978B1 BRPI0110978-2B1A BR0110978A BR0110978B1 BR 0110978 B1 BR0110978 B1 BR 0110978B1 BR 0110978 A BR0110978 A BR 0110978A BR 0110978 B1 BR0110978 B1 BR 0110978B1
- Authority
- BR
- Brazil
- Prior art keywords
- carbon atoms
- straight
- glyphosate
- hydrocarbyl
- hydrogen
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims description 393
- XDDAORKBJWWYJS-UHFFFAOYSA-N glyphosate Chemical compound OC(=O)CNCP(O)(O)=O XDDAORKBJWWYJS-UHFFFAOYSA-N 0.000 title claims description 323
- 239000005562 Glyphosate Substances 0.000 title claims description 277
- 229940097068 glyphosate Drugs 0.000 title claims description 277
- 239000012141 concentrate Substances 0.000 title claims description 122
- 238000009472 formulation Methods 0.000 title description 191
- 125000004432 carbon atom Chemical group C* 0.000 claims description 488
- 239000004094 surface-active agent Substances 0.000 claims description 378
- 125000000217 alkyl group Chemical group 0.000 claims description 368
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 315
- 239000001257 hydrogen Substances 0.000 claims description 299
- 229910052739 hydrogen Inorganic materials 0.000 claims description 299
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 191
- 239000002253 acid Substances 0.000 claims description 165
- 125000003342 alkenyl group Chemical group 0.000 claims description 138
- 230000002363 herbicidal effect Effects 0.000 claims description 125
- 125000002947 alkylene group Chemical group 0.000 claims description 118
- 239000004973 liquid crystal related substance Substances 0.000 claims description 108
- 125000000743 hydrocarbylene group Chemical group 0.000 claims description 103
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 89
- LIOPHZNMBKHGAV-UHFFFAOYSA-M potassium;2-(phosphonomethylamino)acetate Chemical compound [K+].OC(=O)CNCP(O)([O-])=O LIOPHZNMBKHGAV-UHFFFAOYSA-M 0.000 claims description 83
- 150000003839 salts Chemical class 0.000 claims description 82
- 125000003118 aryl group Chemical group 0.000 claims description 71
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 65
- 150000001875 compounds Chemical class 0.000 claims description 64
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 58
- 150000001412 amines Chemical class 0.000 claims description 53
- 125000000304 alkynyl group Chemical group 0.000 claims description 47
- 239000004009 herbicide Substances 0.000 claims description 45
- UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 claims description 38
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 claims description 32
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 claims description 32
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 claims description 28
- 150000001450 anions Chemical class 0.000 claims description 26
- 238000003860 storage Methods 0.000 claims description 26
- 150000002148 esters Chemical class 0.000 claims description 24
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 19
- 125000000623 heterocyclic group Chemical group 0.000 claims description 17
- 229910052757 nitrogen Inorganic materials 0.000 claims description 17
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims description 17
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 15
- 229910052799 carbon Inorganic materials 0.000 claims description 15
- 150000004985 diamines Chemical class 0.000 claims description 15
- 125000004122 cyclic group Chemical group 0.000 claims description 13
- 125000004429 atom Chemical group 0.000 claims description 12
- 239000007788 liquid Substances 0.000 claims description 12
- 229910019142 PO4 Inorganic materials 0.000 claims description 10
- 239000013078 crystal Substances 0.000 claims description 10
- RUCAXVJJQQJZGU-UHFFFAOYSA-M hydron;2-(phosphonatomethylamino)acetate;trimethylsulfanium Chemical compound C[S+](C)C.OP(O)(=O)CNCC([O-])=O RUCAXVJJQQJZGU-UHFFFAOYSA-M 0.000 claims description 10
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 10
- 235000021317 phosphate Nutrition 0.000 claims description 10
- 150000001298 alcohols Chemical class 0.000 claims description 8
- 238000002425 crystallisation Methods 0.000 claims description 8
- 230000008025 crystallization Effects 0.000 claims description 8
- 150000003512 tertiary amines Chemical class 0.000 claims description 5
- 150000003335 secondary amines Chemical class 0.000 claims description 4
- 238000001704 evaporation Methods 0.000 claims description 3
- 230000008020 evaporation Effects 0.000 claims description 3
- 239000004215 Carbon black (E152) Substances 0.000 claims description 2
- PDYXIVPKOMYDOK-UHFFFAOYSA-N Glyphosate-monoammonium Chemical compound [NH4+].OC(=O)CNCP(O)([O-])=O PDYXIVPKOMYDOK-UHFFFAOYSA-N 0.000 claims description 2
- 229930195733 hydrocarbon Natural products 0.000 claims description 2
- 150000002430 hydrocarbons Chemical class 0.000 claims description 2
- 150000002431 hydrogen Chemical group 0.000 claims 20
- 230000003042 antagnostic effect Effects 0.000 claims 2
- 150000003013 phosphoric acid derivatives Chemical class 0.000 claims 2
- DQNPFPHZAUMZHD-UHFFFAOYSA-N 2-aminoethanol;2-(phosphonomethylamino)acetic acid Chemical compound NCCO.OC(=O)CNCP(O)(O)=O DQNPFPHZAUMZHD-UHFFFAOYSA-N 0.000 claims 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 claims 1
- YWICANUUQPYHOW-UHFFFAOYSA-M sodium;2-(phosphonomethylamino)acetate Chemical compound [Na+].OP(O)(=O)CNCC([O-])=O YWICANUUQPYHOW-UHFFFAOYSA-M 0.000 claims 1
- -1 glyphosate acid Chemical class 0.000 description 158
- 241000196324 Embryophyta Species 0.000 description 106
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 89
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 80
- 239000005977 Ethylene Substances 0.000 description 80
- 235000008504 concentrate Nutrition 0.000 description 74
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 67
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 64
- 239000000243 solution Substances 0.000 description 49
- 125000004450 alkenylene group Chemical group 0.000 description 40
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 37
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 37
- 229920001223 polyethylene glycol Polymers 0.000 description 36
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 34
- 239000000047 product Substances 0.000 description 33
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 32
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 28
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 28
- 125000000732 arylene group Chemical group 0.000 description 28
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 27
- 229910052700 potassium Inorganic materials 0.000 description 27
- 239000011591 potassium Substances 0.000 description 27
- 230000015572 biosynthetic process Effects 0.000 description 26
- 238000005755 formation reaction Methods 0.000 description 26
- 238000012360 testing method Methods 0.000 description 26
- 239000003760 tallow Substances 0.000 description 25
- 230000002209 hydrophobic effect Effects 0.000 description 24
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 23
- 125000004419 alkynylene group Chemical group 0.000 description 22
- 150000003973 alkyl amines Chemical group 0.000 description 21
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 20
- 238000002360 preparation method Methods 0.000 description 20
- 229920006395 saturated elastomer Polymers 0.000 description 20
- 239000002904 solvent Substances 0.000 description 20
- 238000000034 method Methods 0.000 description 19
- 239000001993 wax Substances 0.000 description 19
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 18
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 18
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 17
- 238000006243 chemical reaction Methods 0.000 description 17
- 125000006353 oxyethylene group Chemical group 0.000 description 17
- 239000000523 sample Substances 0.000 description 17
- 229910052708 sodium Inorganic materials 0.000 description 17
- 239000011734 sodium Substances 0.000 description 17
- ZEKANFGSDXODPD-UHFFFAOYSA-N glyphosate-isopropylammonium Chemical compound CC(C)N.OC(=O)CNCP(O)(O)=O ZEKANFGSDXODPD-UHFFFAOYSA-N 0.000 description 16
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical group [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 239000003093 cationic surfactant Substances 0.000 description 15
- 125000001453 quaternary ammonium group Chemical group 0.000 description 15
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 14
- 125000000129 anionic group Chemical group 0.000 description 14
- 239000007864 aqueous solution Substances 0.000 description 14
- NARVIWMVBMUEOG-UHFFFAOYSA-N 2-Hydroxy-propylene Natural products CC(O)=C NARVIWMVBMUEOG-UHFFFAOYSA-N 0.000 description 13
- 239000007787 solid Substances 0.000 description 13
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- 125000002091 cationic group Chemical group 0.000 description 12
- 238000007865 diluting Methods 0.000 description 12
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 12
- 235000000346 sugar Nutrition 0.000 description 12
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 11
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 11
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 11
- 239000002671 adjuvant Substances 0.000 description 11
- 230000008901 benefit Effects 0.000 description 11
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 11
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 10
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 10
- 125000001931 aliphatic group Chemical group 0.000 description 10
- 235000013399 edible fruits Nutrition 0.000 description 10
- 239000000575 pesticide Substances 0.000 description 10
- 230000002829 reductive effect Effects 0.000 description 10
- 239000012266 salt solution Substances 0.000 description 10
- 150000003568 thioethers Chemical class 0.000 description 10
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 9
- 108090000790 Enzymes Proteins 0.000 description 9
- 102000004190 Enzymes Human genes 0.000 description 9
- 229920002257 Plurafac® Polymers 0.000 description 9
- 239000004480 active ingredient Substances 0.000 description 9
- 229940088598 enzyme Drugs 0.000 description 9
- 239000000787 lecithin Substances 0.000 description 9
- 229940067606 lecithin Drugs 0.000 description 9
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- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 8
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- ZCSHACFHMFHFKK-UHFFFAOYSA-N 2-methyl-1,3,5-trinitrobenzene;2,4,6-trinitro-1,3,5-triazinane Chemical compound [O-][N+](=O)C1NC([N+]([O-])=O)NC([N+]([O-])=O)N1.CC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O ZCSHACFHMFHFKK-UHFFFAOYSA-N 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 7
- 230000001276 controlling effect Effects 0.000 description 7
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- 239000008367 deionised water Substances 0.000 description 7
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- NQMRYBIKMRVZLB-UHFFFAOYSA-N methylamine hydrochloride Chemical compound [Cl-].[NH3+]C NQMRYBIKMRVZLB-UHFFFAOYSA-N 0.000 description 7
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 7
- 238000011282 treatment Methods 0.000 description 7
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- ZITBHNVGLSVXEF-UHFFFAOYSA-N 2-[2-(16-methylheptadecoxy)ethoxy]ethanol Chemical compound CC(C)CCCCCCCCCCCCCCCOCCOCCO ZITBHNVGLSVXEF-UHFFFAOYSA-N 0.000 description 6
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 6
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- 125000003277 amino group Chemical group 0.000 description 6
- SIPUZPBQZHNSDW-UHFFFAOYSA-N bis(2-methylpropyl)aluminum Chemical compound CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 description 6
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- FZXISNSWEXTPMF-UHFFFAOYSA-N terbutylazine Chemical compound CCNC1=NC(Cl)=NC(NC(C)(C)C)=N1 FZXISNSWEXTPMF-UHFFFAOYSA-N 0.000 description 1
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- SRVJKTDHMYAMHA-WUXMJOGZSA-N thioacetazone Chemical compound CC(=O)NC1=CC=C(\C=N\NC(N)=S)C=C1 SRVJKTDHMYAMHA-WUXMJOGZSA-N 0.000 description 1
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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
- A01N61/00—Biocides, pest repellants or attractants, or plant growth regulators containing substances of unknown or undetermined composition, e.g. substances characterised only by the mode of action
-
- 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
- A01N25/30—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 characterised by the surfactants
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/02—Saturated carboxylic acids or thio analogues thereof; Derivatives thereof
- A01N37/04—Saturated carboxylic acids or thio analogues thereof; Derivatives thereof polybasic
-
- 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
- A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
- A01N57/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds
- A01N57/20—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds containing acyclic or cycloaliphatic radicals
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- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Environmental Sciences (AREA)
- Plant Pathology (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Toxicology (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
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| US20552400P | 2000-05-19 | 2000-05-19 | |
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| US20662800P | 2000-05-24 | 2000-05-24 | |
| US60/206,628 | 2000-05-24 | ||
| US27323401P | 2001-03-02 | 2001-03-02 | |
| US60/273,234 | 2001-03-02 | ||
| US27436801P | 2001-03-08 | 2001-03-08 | |
| US60/274,368 | 2001-03-08 | ||
| PCT/US2001/016550 WO2001089302A2 (en) | 2000-05-19 | 2001-05-21 | Aqueous pesticide formulations and novel surfactants |
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| BR0110978A BR0110978A (pt) | 2004-01-13 |
| BR0110978B1 true BR0110978B1 (pt) | 2015-02-24 |
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2001
- 2001-05-18 MY MYPI20012379A patent/MY158895A/en unknown
- 2001-05-21 CA CA002407751A patent/CA2407751C/en not_active Expired - Lifetime
- 2001-05-21 NZ NZ522396A patent/NZ522396A/en not_active IP Right Cessation
- 2001-05-21 US US09/926,521 patent/US7049270B2/en not_active Expired - Lifetime
- 2001-05-21 PL PL365245A patent/PL223350B1/pl not_active IP Right Cessation
- 2001-05-21 CN CN01812059A patent/CN1444451A/zh active Pending
- 2001-05-21 JP JP2001585556A patent/JP5318313B2/ja not_active Expired - Lifetime
- 2001-05-21 EP EP01937648A patent/EP1343375B1/en not_active Revoked
- 2001-05-21 BR BRPI0110978-2B1A patent/BR0110978B1/pt active IP Right Grant
- 2001-05-21 PL PL410269A patent/PL223390B1/pl unknown
- 2001-05-21 HU HU0302482A patent/HU228374B1/hu unknown
- 2001-05-21 EP EP06013030A patent/EP1721523A3/en not_active Ceased
- 2001-05-21 DE DE60121995T patent/DE60121995T2/de not_active Expired - Lifetime
- 2001-05-21 ES ES01937648T patent/ES2269409T3/es not_active Expired - Lifetime
- 2001-05-21 HN HN2001000105A patent/HN2001000105A/es unknown
- 2001-05-21 WO PCT/US2001/016550 patent/WO2001089302A2/en not_active Ceased
- 2001-05-21 AR ARP010102393A patent/AR028106A1/es not_active Application Discontinuation
- 2001-05-21 AU AU6336101A patent/AU6336101A/xx active Pending
- 2001-05-21 CA CA2510398A patent/CA2510398C/en not_active Expired - Lifetime
- 2001-05-21 MX MXPA02011487 patent/MX265024B/es active IP Right Grant
- 2001-05-21 PH PH12001001235A patent/PH12001001235B1/en unknown
- 2001-05-21 AU AU2001263361A patent/AU2001263361B2/en not_active Expired
- 2001-05-21 AT AT01937648T patent/ATE334591T1/de not_active IP Right Cessation
- 2001-05-22 UY UY26722A patent/UY26722A1/es not_active Application Discontinuation
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2005
- 2005-05-05 US US11/122,454 patent/US20050261130A1/en not_active Abandoned
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2010
- 2010-02-02 US US12/698,636 patent/US10736325B2/en not_active Expired - Fee Related
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