SE522195C2 - Användning av aminföreningar med förbättrad bionedbrytbarhet som effektförhöjande hjälpkemikalier för pesticider och gödningsmedel - Google Patents
Användning av aminföreningar med förbättrad bionedbrytbarhet som effektförhöjande hjälpkemikalier för pesticider och gödningsmedelInfo
- Publication number
- SE522195C2 SE522195C2 SE0002230A SE0002230A SE522195C2 SE 522195 C2 SE522195 C2 SE 522195C2 SE 0002230 A SE0002230 A SE 0002230A SE 0002230 A SE0002230 A SE 0002230A SE 522195 C2 SE522195 C2 SE 522195C2
- Authority
- SE
- Sweden
- Prior art keywords
- carbon atoms
- alkyl group
- propylenediamine
- bishydroxyethyl
- compound
- Prior art date
Links
- -1 amine compounds Chemical class 0.000 title claims abstract description 59
- 239000000575 pesticide Substances 0.000 title claims abstract description 12
- 239000000126 substance Substances 0.000 title claims description 50
- 239000003337 fertilizer Substances 0.000 title claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 32
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 26
- 150000001875 compounds Chemical class 0.000 claims abstract description 24
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 5
- 125000001931 aliphatic group Chemical group 0.000 claims abstract 2
- XDDAORKBJWWYJS-UHFFFAOYSA-N glyphosate Chemical group OC(=O)CNCP(O)(O)=O XDDAORKBJWWYJS-UHFFFAOYSA-N 0.000 claims description 51
- 239000000203 mixture Substances 0.000 claims description 46
- 238000009472 formulation Methods 0.000 claims description 30
- 239000005562 Glyphosate Substances 0.000 claims description 29
- 229940097068 glyphosate Drugs 0.000 claims description 29
- WFDXOXNFNRHQEC-GHRIWEEISA-N azoxystrobin Chemical group CO\C=C(\C(=O)OC)C1=CC=CC=C1OC1=CC(OC=2C(=CC=CC=2)C#N)=NC=N1 WFDXOXNFNRHQEC-GHRIWEEISA-N 0.000 claims description 12
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 claims description 10
- 229910052921 ammonium sulfate Inorganic materials 0.000 claims description 10
- 235000011130 ammonium sulphate Nutrition 0.000 claims description 10
- 230000002363 herbicidal effect Effects 0.000 claims description 10
- 239000004009 herbicide Substances 0.000 claims description 9
- 239000001166 ammonium sulphate Substances 0.000 claims description 8
- 230000002708 enhancing effect Effects 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 6
- 229930182470 glycoside Natural products 0.000 claims description 5
- 239000005730 Azoxystrobin Substances 0.000 claims description 4
- 239000003905 agrochemical Substances 0.000 claims description 4
- 239000003090 pesticide formulation Substances 0.000 claims description 4
- 229940100389 Sulfonylurea Drugs 0.000 claims description 3
- 239000007788 liquid Substances 0.000 claims description 3
- 239000007787 solid Substances 0.000 claims description 3
- 239000000839 emulsion Substances 0.000 claims description 2
- 125000001483 monosaccharide substituent group Chemical group 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 239000000725 suspension Substances 0.000 claims description 2
- 239000012872 agrochemical composition Substances 0.000 claims 2
- YROXIXLRRCOBKF-UHFFFAOYSA-N sulfonylurea Chemical class OC(=N)N=S(=O)=O YROXIXLRRCOBKF-UHFFFAOYSA-N 0.000 claims 1
- 239000000194 fatty acid Substances 0.000 abstract description 65
- 235000014113 dietary fatty acids Nutrition 0.000 abstract description 64
- 229930195729 fatty acid Natural products 0.000 abstract description 64
- 150000004665 fatty acids Chemical class 0.000 abstract description 64
- FKJVYOFPTRGCSP-UHFFFAOYSA-N 2-[3-aminopropyl(2-hydroxyethyl)amino]ethanol Chemical compound NCCCN(CCO)CCO FKJVYOFPTRGCSP-UHFFFAOYSA-N 0.000 abstract description 31
- 239000002671 adjuvant Substances 0.000 abstract description 8
- 239000004094 surface-active agent Substances 0.000 abstract description 5
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 abstract 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical group ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 abstract 1
- 150000001298 alcohols Chemical class 0.000 abstract 1
- 150000004985 diamines Chemical class 0.000 abstract 1
- 235000019387 fatty acid methyl ester Nutrition 0.000 abstract 1
- 235000013162 Cocos nucifera Nutrition 0.000 description 60
- 244000060011 Cocos nucifera Species 0.000 description 60
- 229920001223 polyethylene glycol Polymers 0.000 description 59
- 239000002202 Polyethylene glycol Substances 0.000 description 58
- JVAZJLFFSJARQM-RMPHRYRLSA-N (2r,3r,4s,5s,6r)-2-hexoxy-6-(hydroxymethyl)oxane-3,4,5-triol Chemical compound CCCCCCO[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O JVAZJLFFSJARQM-RMPHRYRLSA-N 0.000 description 54
- 229910052757 nitrogen Inorganic materials 0.000 description 47
- QEVGZEDELICMKH-UHFFFAOYSA-N Diglycolic acid Chemical compound OC(=O)COCC(O)=O QEVGZEDELICMKH-UHFFFAOYSA-N 0.000 description 41
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 40
- CRVGTESFCCXCTH-UHFFFAOYSA-N methyl diethanolamine Chemical compound OCCN(C)CCO CRVGTESFCCXCTH-UHFFFAOYSA-N 0.000 description 27
- 229930182478 glucoside Natural products 0.000 description 21
- AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 description 20
- 150000005690 diesters Chemical class 0.000 description 15
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 13
- 239000000243 solution Substances 0.000 description 12
- PYSGFFTXMUWEOT-UHFFFAOYSA-N 3-(dimethylamino)propan-1-ol Chemical compound CN(C)CCCO PYSGFFTXMUWEOT-UHFFFAOYSA-N 0.000 description 9
- 241000196324 Embryophyta Species 0.000 description 9
- 230000000694 effects Effects 0.000 description 9
- 150000002148 esters Chemical class 0.000 description 9
- FATBGEAMYMYZAF-KTKRTIGZSA-N oleamide Chemical compound CCCCCCCC\C=C/CCCCCCCC(N)=O FATBGEAMYMYZAF-KTKRTIGZSA-N 0.000 description 9
- 229940113162 oleylamide Drugs 0.000 description 9
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 9
- 239000012141 concentrate Substances 0.000 description 8
- LTHNHFOGQMKPOV-UHFFFAOYSA-N 2-ethylhexan-1-amine Chemical compound CCCCC(CC)CN LTHNHFOGQMKPOV-UHFFFAOYSA-N 0.000 description 7
- 240000002791 Brassica napus Species 0.000 description 7
- 150000008131 glucosides Chemical class 0.000 description 7
- 238000005507 spraying Methods 0.000 description 7
- 241000508725 Elymus repens Species 0.000 description 6
- 239000004698 Polyethylene Substances 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- 230000000855 fungicidal effect Effects 0.000 description 6
- 235000011293 Brassica napus Nutrition 0.000 description 5
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 5
- 241000033016 Lolium rigidum Species 0.000 description 5
- 239000011785 micronutrient Substances 0.000 description 5
- 235000013369 micronutrients Nutrition 0.000 description 5
- 229920000573 polyethylene Polymers 0.000 description 5
- 239000000417 fungicide Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- OBETXYAYXDNJHR-UHFFFAOYSA-N 2-Ethylhexanoic acid Chemical compound CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 description 3
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical class NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- 241000736122 Parastagonospora nodorum Species 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- 239000007921 spray Substances 0.000 description 3
- SUZOCIFIGKCISE-UHFFFAOYSA-N 1-(dimethylamino)propan-1-ol Chemical compound CCC(O)N(C)C SUZOCIFIGKCISE-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 235000004977 Brassica sinapistrum Nutrition 0.000 description 2
- 206010061217 Infestation Diseases 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 241000077903 Monococcus Species 0.000 description 2
- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical class CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 2
- ZEKANFGSDXODPD-UHFFFAOYSA-N glyphosate-isopropylammonium Chemical compound CC(C)N.OC(=O)CNCP(O)(O)=O ZEKANFGSDXODPD-UHFFFAOYSA-N 0.000 description 2
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 238000011081 inoculation Methods 0.000 description 2
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical class CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 2
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 2
- 238000003359 percent control normalization Methods 0.000 description 2
- 239000003760 tallow Substances 0.000 description 2
- 238000011282 treatment Methods 0.000 description 2
- 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 description 1
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- GYSCBCSGKXNZRH-UHFFFAOYSA-N 1-benzothiophene-2-carboxamide Chemical compound C1=CC=C2SC(C(=O)N)=CC2=C1 GYSCBCSGKXNZRH-UHFFFAOYSA-N 0.000 description 1
- OVSKIKFHRZPJSS-DOMIDYPGSA-N 2-(2,4-dichlorophenoxy)acetic acid Chemical class OC(=O)[14CH2]OC1=CC=C(Cl)C=C1Cl OVSKIKFHRZPJSS-DOMIDYPGSA-N 0.000 description 1
- LBFFKXDGKVMZQS-UHFFFAOYSA-N 2-(3-aminopropylamino)ethane-1,1-diol Chemical compound NCCCNCC(O)O LBFFKXDGKVMZQS-UHFFFAOYSA-N 0.000 description 1
- SFJPGSCMZIUEDJ-UHFFFAOYSA-N 2-[2-[[carboxy-(2-hydroxy-4-methylphenyl)methyl]amino]ethylamino]-2-(2-hydroxy-4-methylphenyl)acetic acid Chemical compound OC1=CC(C)=CC=C1C(C(O)=O)NCCNC(C(O)=O)C1=CC=C(C)C=C1O SFJPGSCMZIUEDJ-UHFFFAOYSA-N 0.000 description 1
- URDCARMUOSMFFI-UHFFFAOYSA-N 2-[2-[bis(carboxymethyl)amino]ethyl-(2-hydroxyethyl)amino]acetic acid Chemical compound OCCN(CC(O)=O)CCN(CC(O)=O)CC(O)=O URDCARMUOSMFFI-UHFFFAOYSA-N 0.000 description 1
- IAJOBQBIJHVGMQ-UHFFFAOYSA-N 2-amino-4-[hydroxy(methyl)phosphoryl]butanoic acid Chemical compound CP(O)(=O)CCC(N)C(O)=O IAJOBQBIJHVGMQ-UHFFFAOYSA-N 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- CAAMSDWKXXPUJR-UHFFFAOYSA-N 3,5-dihydro-4H-imidazol-4-one Chemical class O=C1CNC=N1 CAAMSDWKXXPUJR-UHFFFAOYSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- RSNKLLQCBHWBKB-IBYNPJLGSA-N CCCCC(CC)CC(=O)[C@@H]([C@H]([C@@H]([C@@H](CO)O)O)O)O Chemical compound CCCCC(CC)CC(=O)[C@@H]([C@H]([C@@H]([C@@H](CO)O)O)O)O RSNKLLQCBHWBKB-IBYNPJLGSA-N 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical class NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- GHVNFZFCNZKVNT-UHFFFAOYSA-N Decanoic acid Natural products CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 1
- 239000005504 Dicamba Chemical class 0.000 description 1
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 1
- 239000005767 Epoxiconazole Substances 0.000 description 1
- 206010015946 Eye irritation Diseases 0.000 description 1
- 239000005561 Glufosinate Substances 0.000 description 1
- 239000005639 Lauric acid Substances 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 1
- QPCDCPDFJACHGM-UHFFFAOYSA-N N,N-bis{2-[bis(carboxymethyl)amino]ethyl}glycine Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(=O)O)CCN(CC(O)=O)CC(O)=O QPCDCPDFJACHGM-UHFFFAOYSA-N 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 231100000674 Phytotoxicity Toxicity 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 239000005822 Propiconazole Substances 0.000 description 1
- 229930182692 Strobilurin Natural products 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- WHKUVVPPKQRRBV-UHFFFAOYSA-N Trasan Chemical class CC1=CC(Cl)=CC=C1OCC(O)=O WHKUVVPPKQRRBV-UHFFFAOYSA-N 0.000 description 1
- 241000209140 Triticum Species 0.000 description 1
- 235000021307 Triticum Nutrition 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 230000000895 acaricidal effect Effects 0.000 description 1
- 239000000642 acaricide Substances 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- ZXKINMCYCKHYFR-UHFFFAOYSA-N aminooxidanide Chemical compound [O-]N ZXKINMCYCKHYFR-UHFFFAOYSA-N 0.000 description 1
- 230000002528 anti-freeze Effects 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- GINJFDRNADDBIN-FXQIFTODSA-N bilanafos Chemical class OC(=O)[C@H](C)NC(=O)[C@H](C)NC(=O)[C@@H](N)CCP(C)(O)=O GINJFDRNADDBIN-FXQIFTODSA-N 0.000 description 1
- 231100000209 biodegradability test Toxicity 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- 239000002738 chelating agent Substances 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 239000008139 complexing agent Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- IWEDIXLBFLAXBO-UHFFFAOYSA-N dicamba Chemical class COC1=C(Cl)C=CC(Cl)=C1C(O)=O IWEDIXLBFLAXBO-UHFFFAOYSA-N 0.000 description 1
- 150000004656 dimethylamines Chemical class 0.000 description 1
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical class C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- PZZHMLOHNYWKIK-UHFFFAOYSA-N eddha Chemical compound C=1C=CC=C(O)C=1C(C(=O)O)NCCNC(C(O)=O)C1=CC=CC=C1O PZZHMLOHNYWKIK-UHFFFAOYSA-N 0.000 description 1
- 238000007046 ethoxylation reaction Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 231100000013 eye irritation Toxicity 0.000 description 1
- 150000002191 fatty alcohols Chemical class 0.000 description 1
- 239000002657 fibrous material Substances 0.000 description 1
- 239000003349 gelling agent Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 239000003630 growth substance Substances 0.000 description 1
- XPXMKIXDFWLRAA-UHFFFAOYSA-N hydrazinide Chemical compound [NH-]N XPXMKIXDFWLRAA-UHFFFAOYSA-N 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 125000001165 hydrophobic group Chemical group 0.000 description 1
- 239000003752 hydrotrope Substances 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 235000021073 macronutrients Nutrition 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000004530 micro-emulsion Substances 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 239000011733 molybdenum Substances 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 125000001117 oleyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])/C([H])=C([H])\C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000003755 preservative agent Substances 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
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
- 238000006462 rearrangement reaction Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- NRZWQKGABZFFKE-UHFFFAOYSA-N trimethylsulfonium Chemical class C[S+](C)C NRZWQKGABZFFKE-UHFFFAOYSA-N 0.000 description 1
- 239000012224 working solution Substances 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/34—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups
- C07C233/35—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
- C07C233/36—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom having the carbon atom of the carboxamide group bound to a hydrogen atom or to a carbon atom of an acyclic saturated carbon skeleton
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C05—FERTILISERS; MANUFACTURE THEREOF
- C05G—MIXTURES OF FERTILISERS COVERED INDIVIDUALLY BY DIFFERENT SUBCLASSES OF CLASS C05; MIXTURES OF ONE OR MORE FERTILISERS WITH MATERIALS NOT HAVING A SPECIFIC FERTILISING ACTIVITY, e.g. PESTICIDES, SOIL-CONDITIONERS, WETTING AGENTS; FERTILISERS CHARACTERISED BY THEIR FORM
- C05G3/00—Mixtures of one or more fertilisers with additives not having a specially fertilising activity
- C05G3/50—Surfactants; Emulsifiers
-
- C—CHEMISTRY; METALLURGY
- C05—FERTILISERS; MANUFACTURE THEREOF
- C05G—MIXTURES OF FERTILISERS COVERED INDIVIDUALLY BY DIFFERENT SUBCLASSES OF CLASS C05; MIXTURES OF ONE OR MORE FERTILISERS WITH MATERIALS NOT HAVING A SPECIFIC FERTILISING ACTIVITY, e.g. PESTICIDES, SOIL-CONDITIONERS, WETTING AGENTS; FERTILISERS CHARACTERISED BY THEIR FORM
- C05G3/00—Mixtures of one or more fertilisers with additives not having a specially fertilising activity
- C05G3/60—Biocides or preservatives, e.g. disinfectants, pesticides or herbicides; Pest repellants or attractants
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C219/00—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton
- C07C219/02—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton having esterified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C219/04—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton having esterified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C219/06—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton having esterified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having the hydroxy groups esterified by carboxylic acids having the esterifying carboxyl groups bound to hydrogen atoms or to acyclic carbon atoms of an acyclic saturated carbon skeleton
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pest Control & Pesticides (AREA)
- General Health & Medical Sciences (AREA)
- Health & Medical Sciences (AREA)
- Plant Pathology (AREA)
- Toxicology (AREA)
- Agronomy & Crop Science (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Fertilizers (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (18)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE0002230A SE522195C2 (sv) | 2000-06-15 | 2000-06-15 | Användning av aminföreningar med förbättrad bionedbrytbarhet som effektförhöjande hjälpkemikalier för pesticider och gödningsmedel |
| ARP010102469A AR028616A1 (es) | 2000-06-15 | 2001-05-23 | El uso de compuestos de amina con una biodegradabilidad mejorada como pesticidas y fertilizantes |
| AU2001264457A AU2001264457B2 (en) | 2000-06-15 | 2001-05-25 | Use of amine compounds with improved biodegradability as adjuvants for pesticides and fertilisers |
| CNB018111262A CN1207965C (zh) | 2000-06-15 | 2001-05-25 | 生物降解性改良的胺化合物作为农药和肥料的助剂的应用 |
| JP2002509916A JP4860887B2 (ja) | 2000-06-15 | 2001-05-25 | 改善された生分解性を有するアミン化合物の、農薬および肥料に対する補助剤としての使用 |
| BRPI0111549-9A BRPI0111549B1 (pt) | 2000-06-15 | 2001-05-25 | Use of amine compounds with improved biodegradability, as an advocate for pesticides and fertilizers |
| US10/297,853 US6747164B2 (en) | 2000-06-15 | 2001-05-25 | Use of amine compounds with improved biodegradability as adjuvants for pesticides and fertilizers |
| PCT/SE2001/001178 WO2001095720A1 (en) | 2000-06-15 | 2001-05-25 | Use of amine compounds with improved biodegradability as adjuvants for pesticides and fertilisers |
| ES01938886T ES2230319T3 (es) | 2000-06-15 | 2001-05-25 | Uso de compuestos aminicos con biodegradabilidad mejorada como adyuvantes para pesticidas y plaguicidas. |
| KR1020027016980A KR100787071B1 (ko) | 2000-06-15 | 2001-05-25 | 살충제 및 비료용의 아주번트로서 개선된 생분해성을 지닌아민 화합물의 용도 |
| EP01938886A EP1289362B1 (de) | 2000-06-15 | 2001-05-25 | Verwendung von aminverbindungen mit verbesserter bioabbaubarkeit als zusatz für pestizide und düngemittel |
| CA002407568A CA2407568A1 (en) | 2000-06-15 | 2001-05-25 | Use of amine compounds with improved biodegradability as adjuvants for pesticides and fertilisers |
| DE60106241T DE60106241T2 (de) | 2000-06-15 | 2001-05-25 | Verwendung von aminverbindungen mit verbesserter bioabbaubarkeit als zusatz für pestizide und düngemittel |
| AT01938886T ATE278320T1 (de) | 2000-06-15 | 2001-05-25 | Verwendung von aminverbindungen mit verbesserter bioabbaubarkeit als zusatz für pestizide und düngemittel |
| AU6445701A AU6445701A (en) | 2000-06-15 | 2001-05-25 | Use of amine compounds with improved biodegradability as adjuvants for pesticides and fertilisers |
| MYPI20012682 MY127118A (en) | 2000-06-15 | 2001-06-08 | Use of amine compounds with improved biodegradability as adjuvants for pesticides and fertilisers |
| PE2001000565A PE20020281A1 (es) | 2000-06-15 | 2001-06-14 | Composiciones que contienen compuestos de amina con biodegradabilidad mejorada como adyuvantes para pesticidas y fertilizantes |
| ZA200208641A ZA200208641B (en) | 2000-06-15 | 2002-10-25 | Use of amine compounds with improved biodegradability as adjuvants for pesticides and fertilisers. |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE0002230A SE522195C2 (sv) | 2000-06-15 | 2000-06-15 | Användning av aminföreningar med förbättrad bionedbrytbarhet som effektförhöjande hjälpkemikalier för pesticider och gödningsmedel |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| SE0002230D0 SE0002230D0 (sv) | 2000-06-15 |
| SE0002230L SE0002230L (sv) | 2001-12-16 |
| SE522195C2 true SE522195C2 (sv) | 2004-01-20 |
Family
ID=20280092
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SE0002230A SE522195C2 (sv) | 2000-06-15 | 2000-06-15 | Användning av aminföreningar med förbättrad bionedbrytbarhet som effektförhöjande hjälpkemikalier för pesticider och gödningsmedel |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US6747164B2 (de) |
| EP (1) | EP1289362B1 (de) |
| JP (1) | JP4860887B2 (de) |
| KR (1) | KR100787071B1 (de) |
| CN (1) | CN1207965C (de) |
| AR (1) | AR028616A1 (de) |
| AT (1) | ATE278320T1 (de) |
| AU (2) | AU2001264457B2 (de) |
| BR (1) | BRPI0111549B1 (de) |
| CA (1) | CA2407568A1 (de) |
| DE (1) | DE60106241T2 (de) |
| ES (1) | ES2230319T3 (de) |
| MY (1) | MY127118A (de) |
| PE (1) | PE20020281A1 (de) |
| SE (1) | SE522195C2 (de) |
| WO (1) | WO2001095720A1 (de) |
| ZA (1) | ZA200208641B (de) |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20040138176A1 (en) * | 2002-05-31 | 2004-07-15 | Cjb Industries, Inc. | Adjuvant for pesticides |
| EP2094083B1 (de) * | 2006-12-06 | 2014-07-23 | Akzo Nobel N.V. | Alkylamidopropyl-dialkylamin-tenside als adjuvanzien |
| US9012365B2 (en) * | 2006-12-06 | 2015-04-21 | Akzo Nobel N.V. | Compatibility agents for herbicidal formulations comprising 2,4-(Dichlorophenoxy) acetic acid salts |
| WO2008105964A1 (en) * | 2007-02-26 | 2008-09-04 | Stepan Company | Adjuvants for agricultural applications |
| CA2925709C (en) * | 2007-12-21 | 2019-11-26 | Huntsman Petrochemical Llc | Method of preparing amidoamine alkoxylates and compositions thereof |
| BRPI0915368B1 (pt) | 2008-07-03 | 2019-01-15 | Monsanto Technology Llc | composição compreendendo glifosato ou um sal ou um ester de glifosato e método de controlar crescimento de planta |
| CN102215695B (zh) * | 2008-09-29 | 2014-10-08 | 孟山都技术公司 | 包含酰胺基烷基胺表面活性剂的草甘膦制剂 |
| EP2263456A1 (de) * | 2009-06-18 | 2010-12-22 | LANXESS Deutschland GmbH | Amidoalkylaminhaltige Azol-Zusammensetzungen für den Schutz technischer Materialien |
| BR112012011625B1 (pt) | 2009-11-16 | 2018-10-02 | Imtrade Australia Pty Ltd | formulações de glifosato de carga elevada e processo de preparação das mesmas |
| BR112013009966B1 (pt) | 2010-10-25 | 2019-04-09 | Stepan Company | Amina graxa, amidoamina graxa, derivado, formulação deglifosato, limpador de superfície áspera, formulação de detergente para vestuário sujo, produto de limpeza pessoalou sabonete, dispersante de parafina, espumante de poço de gás, inibidor de corrosão para uso em aplicações de campo petrolífero, tinta ou composição aditiva de revestimento,espumante, aditivo de espuma ou dispersante para uso em gesso, concreto ou aplicações de combate a incêndios |
| MX339493B (es) | 2010-10-25 | 2016-05-26 | Stepan Co | Esteraminas y derivados de la metatesis de aceite natural. |
| ES2702807T3 (es) * | 2010-10-25 | 2019-03-05 | Stepan Co | Formulaciones de glifosato basadas en composiciones derivadas de metátesis de aceites naturales |
| EP2520166A1 (de) * | 2011-05-04 | 2012-11-07 | Taminco | Neue Bisaminpropylamide und Verwendungen davon in Landwirtschafts- und Reinigungsmittelzusammensetzungen |
| EP2967048A1 (de) * | 2013-03-14 | 2016-01-20 | Akzo Nobel Chemicals International B.V. | Stickstoffhaltige tenside mit alkoxylierung auf der hydroxylgruppe von fettketten |
| PL3454658T3 (pl) | 2016-05-11 | 2025-04-14 | Monsanto Technology Llc | Formulacje glifosatu zawierające amidoalkiloaminowe środki powierzchniowo czynne |
| EP3538509B1 (de) | 2016-11-08 | 2023-04-12 | Rhodia Operations | Verfahren zur herstellung von endverbindungen von internen ketonen, die bei der decarboxylativen ketonisierung von fettsäuren oder fettsäurederivaten ausgegeben werden |
| IT201700095717A1 (it) | 2017-08-24 | 2019-02-24 | Lamberti Spa | Composizione erbicida |
| PL234744B1 (pl) * | 2017-09-22 | 2020-03-31 | Icb Pharma Spolka Jawna Tomasz Swietoslawski Pawel Swietoslawski | Ciekły adiuwant do pestycydów |
| US20210076670A1 (en) * | 2018-02-23 | 2021-03-18 | Nouryon Chemicals International B.V. | Pesticide suspension concentrate and fertilizer composition therewith |
Family Cites Families (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL172234C (nl) | 1971-06-02 | 1983-08-01 | Hoechst Ag | Werkwijze voor het bereiden van geperfluoreerde carbonzuuramideamineverbindingen. |
| DE2641286A1 (de) * | 1975-11-12 | 1977-06-02 | Texaco Development Corp | Quartaere ammoniumverbindung und ihre verwendung |
| US4228042A (en) * | 1978-06-26 | 1980-10-14 | The Procter & Gamble Company | Biodegradable cationic surface-active agents containing ester or amide and polyalkoxy group |
| EP0257686B1 (de) * | 1986-08-20 | 1991-02-06 | Akzo N.V. | Herbizide und Fungizide, die wirkungserhöhende Zusätze enthalten |
| DE3636750A1 (de) | 1986-10-29 | 1988-05-05 | Henkel Kgaa | Amphotere und zwitterionische phosphattenside |
| JP3167208B2 (ja) * | 1993-02-17 | 2001-05-21 | 花王株式会社 | エステル基を有するアミノ化合物の保存方法 |
| JP3382363B2 (ja) * | 1993-08-03 | 2003-03-04 | 花王株式会社 | 農薬用効力増強剤及び農薬組成物 |
| US5563111A (en) | 1993-08-03 | 1996-10-08 | Kao Corporation | Agricultural chemical composition comprising amine surfactants with at least one ester or amide linkage |
| JP3382398B2 (ja) * | 1993-12-17 | 2003-03-04 | 花王株式会社 | 農薬用効力増強剤及び農薬組成物 |
| JP3339956B2 (ja) * | 1994-02-14 | 2002-10-28 | 花王株式会社 | 農薬用効力増強剤及び農薬組成物 |
| FR2737390B1 (fr) | 1995-08-04 | 1997-09-19 | Rhone Poulenc Chimie | Composition phytosanitaire hydrosoluble comprenant au moins des amidoamines polyacoxylees |
| JP3871730B2 (ja) * | 1996-04-08 | 2007-01-24 | 花王株式会社 | 新規な第４級アンモニウム塩、その製造法及び界面活性剤組成物、並びにそれを含有する毛髪化粧料 |
| US6107498A (en) | 1997-04-22 | 2000-08-22 | Akzo Nobel N.V. | Process for making carboxylic amides |
| FR2782244B1 (fr) | 1998-08-12 | 2000-09-15 | Rhodia Chimie Sa | Formulations phytosanitaires a forte teneur en matiere active |
| GB9819693D0 (en) * | 1998-09-10 | 1998-11-04 | Zeneca Ltd | Glyphosate formulation |
| DE19953274A1 (de) * | 1999-11-05 | 2001-05-10 | Cognis Deutschland Gmbh | Emulsionen |
-
2000
- 2000-06-15 SE SE0002230A patent/SE522195C2/sv not_active IP Right Cessation
-
2001
- 2001-05-23 AR ARP010102469A patent/AR028616A1/es active IP Right Grant
- 2001-05-25 CN CNB018111262A patent/CN1207965C/zh not_active Expired - Fee Related
- 2001-05-25 EP EP01938886A patent/EP1289362B1/de not_active Expired - Lifetime
- 2001-05-25 BR BRPI0111549-9A patent/BRPI0111549B1/pt not_active IP Right Cessation
- 2001-05-25 WO PCT/SE2001/001178 patent/WO2001095720A1/en not_active Ceased
- 2001-05-25 DE DE60106241T patent/DE60106241T2/de not_active Expired - Lifetime
- 2001-05-25 AU AU2001264457A patent/AU2001264457B2/en not_active Expired
- 2001-05-25 KR KR1020027016980A patent/KR100787071B1/ko not_active Expired - Fee Related
- 2001-05-25 AU AU6445701A patent/AU6445701A/xx active Pending
- 2001-05-25 AT AT01938886T patent/ATE278320T1/de not_active IP Right Cessation
- 2001-05-25 CA CA002407568A patent/CA2407568A1/en not_active Abandoned
- 2001-05-25 JP JP2002509916A patent/JP4860887B2/ja not_active Expired - Fee Related
- 2001-05-25 ES ES01938886T patent/ES2230319T3/es not_active Expired - Lifetime
- 2001-05-25 US US10/297,853 patent/US6747164B2/en not_active Expired - Lifetime
- 2001-06-08 MY MYPI20012682 patent/MY127118A/en unknown
- 2001-06-14 PE PE2001000565A patent/PE20020281A1/es not_active Application Discontinuation
-
2002
- 2002-10-25 ZA ZA200208641A patent/ZA200208641B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| PE20020281A1 (es) | 2002-04-09 |
| AU2001264457B2 (en) | 2005-01-06 |
| JP2004503474A (ja) | 2004-02-05 |
| ES2230319T3 (es) | 2005-05-01 |
| KR100787071B1 (ko) | 2007-12-21 |
| CN1207965C (zh) | 2005-06-29 |
| ATE278320T1 (de) | 2004-10-15 |
| CA2407568A1 (en) | 2001-12-20 |
| MY127118A (en) | 2006-11-30 |
| WO2001095720A1 (en) | 2001-12-20 |
| DE60106241D1 (de) | 2004-11-11 |
| EP1289362B1 (de) | 2004-10-06 |
| BRPI0111549B1 (pt) | 2017-06-20 |
| ZA200208641B (en) | 2003-05-19 |
| DE60106241T2 (de) | 2006-03-02 |
| CN1436042A (zh) | 2003-08-13 |
| KR20030010699A (ko) | 2003-02-05 |
| BR0111549A (pt) | 2003-05-06 |
| EP1289362A1 (de) | 2003-03-12 |
| SE0002230L (sv) | 2001-12-16 |
| US20030176286A1 (en) | 2003-09-18 |
| SE0002230D0 (sv) | 2000-06-15 |
| US6747164B2 (en) | 2004-06-08 |
| AU6445701A (en) | 2001-12-24 |
| JP4860887B2 (ja) | 2012-01-25 |
| AR028616A1 (es) | 2003-05-14 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| NUG | Patent has lapsed |