DE69412200T2 - Landwirtschaftliche formulierungen enthaltend flüssige estern von fluroxypyr - Google Patents
Landwirtschaftliche formulierungen enthaltend flüssige estern von fluroxypyrInfo
- Publication number
- DE69412200T2 DE69412200T2 DE69412200T DE69412200T DE69412200T2 DE 69412200 T2 DE69412200 T2 DE 69412200T2 DE 69412200 T DE69412200 T DE 69412200T DE 69412200 T DE69412200 T DE 69412200T DE 69412200 T2 DE69412200 T2 DE 69412200T2
- Authority
- DE
- Germany
- Prior art keywords
- ester
- propoxy
- fluroxypyr
- formulation according
- propyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
- 239000000203 mixture Substances 0.000 title claims description 120
- 150000002148 esters Chemical class 0.000 title claims description 47
- 239000005558 Fluroxypyr Substances 0.000 title claims description 36
- MEFQWPUMEMWTJP-UHFFFAOYSA-N fluroxypyr Chemical compound NC1=C(Cl)C(F)=NC(OCC(O)=O)=C1Cl MEFQWPUMEMWTJP-UHFFFAOYSA-N 0.000 title claims description 31
- 239000007788 liquid Substances 0.000 title claims description 25
- 238000009472 formulation Methods 0.000 claims description 94
- -1 1-butoxy-2-propyl Chemical group 0.000 claims description 47
- 239000002904 solvent Substances 0.000 claims description 27
- 239000000839 emulsion Substances 0.000 claims description 26
- 239000004495 emulsifiable concentrate Substances 0.000 claims description 24
- 230000002363 herbicidal effect Effects 0.000 claims description 17
- 239000004563 wettable powder Substances 0.000 claims description 17
- 239000004009 herbicide Substances 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 12
- 239000004562 water dispersible granule Substances 0.000 claims description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 10
- 239000007921 spray Substances 0.000 claims description 7
- NPSJHQMIVNJLNN-UHFFFAOYSA-N 2-ethylhexyl 4-nitrobenzoate Chemical compound CCCCC(CC)COC(=O)C1=CC=C([N+]([O-])=O)C=C1 NPSJHQMIVNJLNN-UHFFFAOYSA-N 0.000 claims description 3
- 239000004808 2-ethylhexylester Substances 0.000 claims description 3
- 239000005484 Bifenox Substances 0.000 claims description 3
- SUSRORUBZHMPCO-UHFFFAOYSA-N MC-4379 Chemical compound C1=C([N+]([O-])=O)C(C(=O)OC)=CC(OC=2C(=CC(Cl)=CC=2)Cl)=C1 SUSRORUBZHMPCO-UHFFFAOYSA-N 0.000 claims description 3
- 239000005582 Metosulam Substances 0.000 claims description 3
- VGHPMIFEKOFHHQ-UHFFFAOYSA-N Metosulam Chemical group N1=C2N=C(OC)C=C(OC)N2N=C1S(=O)(=O)NC1=C(Cl)C=CC(C)=C1Cl VGHPMIFEKOFHHQ-UHFFFAOYSA-N 0.000 claims description 3
- 238000007865 diluting Methods 0.000 claims description 3
- 239000002253 acid Substances 0.000 description 23
- 239000004094 surface-active agent Substances 0.000 description 22
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 20
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 15
- 239000000377 silicon dioxide Substances 0.000 description 10
- 239000000017 hydrogel Substances 0.000 description 9
- 239000012071 phase Substances 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- 230000005484 gravity Effects 0.000 description 8
- 239000002736 nonionic surfactant Substances 0.000 description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 7
- 239000000546 pharmaceutical excipient Substances 0.000 description 7
- 150000003839 salts Chemical class 0.000 description 7
- 239000004480 active ingredient Substances 0.000 description 6
- OOCMUZJPDXYRFD-UHFFFAOYSA-L calcium;2-dodecylbenzenesulfonate Chemical compound [Ca+2].CCCCCCCCCCCCC1=CC=CC=C1S([O-])(=O)=O.CCCCCCCCCCCCC1=CC=CC=C1S([O-])(=O)=O OOCMUZJPDXYRFD-UHFFFAOYSA-L 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- 239000002563 ionic surfactant Substances 0.000 description 6
- 239000003960 organic solvent Substances 0.000 description 6
- YKRFAFDBPCHDFG-UHFFFAOYSA-N 2-ethylhexyl 2-(4-amino-3,5-dichloro-6-fluoropyridin-2-yl)oxyacetate Chemical compound CCCCC(CC)COC(=O)COC1=NC(F)=C(Cl)C(N)=C1Cl YKRFAFDBPCHDFG-UHFFFAOYSA-N 0.000 description 5
- 239000002270 dispersing agent Substances 0.000 description 5
- 230000008014 freezing Effects 0.000 description 5
- 238000007710 freezing Methods 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 229920005682 EO-PO block copolymer Polymers 0.000 description 4
- 239000004372 Polyvinyl alcohol Substances 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 230000000994 depressogenic effect Effects 0.000 description 4
- 239000004615 ingredient Substances 0.000 description 4
- UQDUPQYQJKYHQI-UHFFFAOYSA-N methyl laurate Chemical compound CCCCCCCCCCCC(=O)OC UQDUPQYQJKYHQI-UHFFFAOYSA-N 0.000 description 4
- 229920000847 nonoxynol Polymers 0.000 description 4
- 229920002451 polyvinyl alcohol Polymers 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 238000009736 wetting Methods 0.000 description 4
- CUVLMZNMSPJDON-UHFFFAOYSA-N 1-(1-butoxypropan-2-yloxy)propan-2-ol Chemical compound CCCCOCC(C)OCC(C)O CUVLMZNMSPJDON-UHFFFAOYSA-N 0.000 description 3
- RWNUSVWFHDHRCJ-UHFFFAOYSA-N 1-butoxypropan-2-ol Chemical compound CCCCOCC(C)O RWNUSVWFHDHRCJ-UHFFFAOYSA-N 0.000 description 3
- VATRWWPJWVCZTA-UHFFFAOYSA-N 3-oxo-n-[2-(trifluoromethyl)phenyl]butanamide Chemical compound CC(=O)CC(=O)NC1=CC=CC=C1C(F)(F)F VATRWWPJWVCZTA-UHFFFAOYSA-N 0.000 description 3
- 241000196324 Embryophyta Species 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 239000012736 aqueous medium Substances 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 230000000704 physical effect Effects 0.000 description 3
- 239000002562 thickening agent Substances 0.000 description 3
- 235000015112 vegetable and seed oil Nutrition 0.000 description 3
- 239000008158 vegetable oil Substances 0.000 description 3
- QPHFJZRSMXHTAW-UHFFFAOYSA-N 1-[2-(2-methoxypropoxy)propoxy]butane Chemical compound CCCCOCC(C)OCC(C)OC QPHFJZRSMXHTAW-UHFFFAOYSA-N 0.000 description 2
- GZEYORSRDNLAPB-UHFFFAOYSA-N 1-butoxybutan-2-ol Chemical compound CCCCOCC(O)CC GZEYORSRDNLAPB-UHFFFAOYSA-N 0.000 description 2
- IEORSVTYLWZQJQ-UHFFFAOYSA-N 2-(2-nonylphenoxy)ethanol Chemical compound CCCCCCCCCC1=CC=CC=C1OCCO IEORSVTYLWZQJQ-UHFFFAOYSA-N 0.000 description 2
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 2
- QCAHUFWKIQLBNB-UHFFFAOYSA-N 3-(3-methoxypropoxy)propan-1-ol Chemical compound COCCCOCCCO QCAHUFWKIQLBNB-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- ULUAUXLGCMPNKK-UHFFFAOYSA-N Sulfobutanedioic acid Chemical compound OC(=O)CC(C(O)=O)S(O)(=O)=O ULUAUXLGCMPNKK-UHFFFAOYSA-N 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 239000002671 adjuvant Substances 0.000 description 2
- 230000002411 adverse Effects 0.000 description 2
- 238000005054 agglomeration Methods 0.000 description 2
- 230000002776 aggregation Effects 0.000 description 2
- 239000003945 anionic surfactant Substances 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 235000013877 carbamide Nutrition 0.000 description 2
- MZZBPDKVEFVLFF-UHFFFAOYSA-N cyanazine Chemical compound CCNC1=NC(Cl)=NC(NC(C)(C)C#N)=N1 MZZBPDKVEFVLFF-UHFFFAOYSA-N 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- QYDYPVFESGNLHU-UHFFFAOYSA-N elaidic acid methyl ester Natural products CCCCCCCCC=CCCCCCCCC(=O)OC QYDYPVFESGNLHU-UHFFFAOYSA-N 0.000 description 2
- 150000002191 fatty alcohols Chemical class 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 2
- 239000012669 liquid formulation Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- QYDYPVFESGNLHU-KHPPLWFESA-N methyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC QYDYPVFESGNLHU-KHPPLWFESA-N 0.000 description 2
- 229940073769 methyl oleate Drugs 0.000 description 2
- 239000007764 o/w emulsion Substances 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- DQKWXTIYGWPGOO-UHFFFAOYSA-N (2,6-dibromo-4-cyanophenyl) octanoate Chemical compound CCCCCCCC(=O)OC1=C(Br)C=C(C#N)C=C1Br DQKWXTIYGWPGOO-UHFFFAOYSA-N 0.000 description 1
- LNAZSHAWQACDHT-XIYTZBAFSA-N (2r,3r,4s,5r,6s)-4,5-dimethoxy-2-(methoxymethyl)-3-[(2s,3r,4s,5r,6r)-3,4,5-trimethoxy-6-(methoxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6r)-4,5,6-trimethoxy-2-(methoxymethyl)oxan-3-yl]oxyoxane Chemical compound CO[C@@H]1[C@@H](OC)[C@H](OC)[C@@H](COC)O[C@H]1O[C@H]1[C@H](OC)[C@@H](OC)[C@H](O[C@H]2[C@@H]([C@@H](OC)[C@H](OC)O[C@@H]2COC)OC)O[C@@H]1COC LNAZSHAWQACDHT-XIYTZBAFSA-N 0.000 description 1
- HPFDGTFXAVIVTH-UHFFFAOYSA-N 1-((1-((1-Methoxypropan-2-yl)oxy)propan-2-yl)oxy)propan-2-ol Chemical compound COCC(C)OCC(C)OCC(C)O HPFDGTFXAVIVTH-UHFFFAOYSA-N 0.000 description 1
- WGYZMNBUZFHYRX-UHFFFAOYSA-N 1-(1-methoxypropan-2-yloxy)propan-2-ol Chemical compound COCC(C)OCC(C)O WGYZMNBUZFHYRX-UHFFFAOYSA-N 0.000 description 1
- XFRVVPUIAFSTFO-UHFFFAOYSA-N 1-Tridecanol Chemical compound CCCCCCCCCCCCCO XFRVVPUIAFSTFO-UHFFFAOYSA-N 0.000 description 1
- LORVPHHKJFSORQ-UHFFFAOYSA-N 1-[1-(1-butoxypropan-2-yloxy)propan-2-yloxy]propan-2-ol Chemical compound CCCCOCC(C)OCC(C)OCC(C)O LORVPHHKJFSORQ-UHFFFAOYSA-N 0.000 description 1
- IDQBJILTOGBZCR-UHFFFAOYSA-N 1-butoxypropan-1-ol Chemical compound CCCCOC(O)CC IDQBJILTOGBZCR-UHFFFAOYSA-N 0.000 description 1
- 239000005631 2,4-Dichlorophenoxyacetic acid Substances 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- GOCUAJYOYBLQRH-UHFFFAOYSA-N 2-(4-{[3-chloro-5-(trifluoromethyl)pyridin-2-yl]oxy}phenoxy)propanoic acid Chemical compound C1=CC(OC(C)C(O)=O)=CC=C1OC1=NC=C(C(F)(F)F)C=C1Cl GOCUAJYOYBLQRH-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- GVZNXUAPPLHUOM-UHFFFAOYSA-N 2-[1-(1-methoxypropan-2-yloxy)propan-2-yloxy]propan-1-ol Chemical compound COCC(C)OCC(C)OC(C)CO GVZNXUAPPLHUOM-UHFFFAOYSA-N 0.000 description 1
- JDSQBDGCMUXRBM-UHFFFAOYSA-N 2-[2-(2-butoxypropoxy)propoxy]propan-1-ol Chemical compound CCCCOC(C)COC(C)COC(C)CO JDSQBDGCMUXRBM-UHFFFAOYSA-N 0.000 description 1
- WAEVWDZKMBQDEJ-UHFFFAOYSA-N 2-[2-(2-methoxypropoxy)propoxy]propan-1-ol Chemical compound COC(C)COC(C)COC(C)CO WAEVWDZKMBQDEJ-UHFFFAOYSA-N 0.000 description 1
- OOLBCHYXZDXLDS-UHFFFAOYSA-N 2-[4-(2,4-dichlorophenoxy)phenoxy]propanoic acid Chemical compound C1=CC(OC(C)C(O)=O)=CC=C1OC1=CC=C(Cl)C=C1Cl OOLBCHYXZDXLDS-UHFFFAOYSA-N 0.000 description 1
- MPPOHAUSNPTFAJ-UHFFFAOYSA-N 2-[4-[(6-chloro-1,3-benzoxazol-2-yl)oxy]phenoxy]propanoic acid Chemical compound C1=CC(OC(C)C(O)=O)=CC=C1OC1=NC2=CC=C(Cl)C=C2O1 MPPOHAUSNPTFAJ-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
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- UDXVMLIGVOVHGW-UHFFFAOYSA-N 7,10-dioxadispiro[2.2.4^{6}.2^{3}]dodecane Chemical compound C1CC11CCC2(OCCO2)CC1 UDXVMLIGVOVHGW-UHFFFAOYSA-N 0.000 description 1
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- VEUUMBGHMNQHGO-UHFFFAOYSA-N ethyl chloroacetate Chemical compound CCOC(=O)CCl VEUUMBGHMNQHGO-UHFFFAOYSA-N 0.000 description 1
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- XDDAORKBJWWYJS-UHFFFAOYSA-N glyphosate Chemical compound OC(=O)CNCP(O)(O)=O XDDAORKBJWWYJS-UHFFFAOYSA-N 0.000 description 1
- 229940097068 glyphosate Drugs 0.000 description 1
- 229920000578 graft copolymer Polymers 0.000 description 1
- 239000000665 guar gum Substances 0.000 description 1
- 235000010417 guar gum Nutrition 0.000 description 1
- 229960002154 guar gum Drugs 0.000 description 1
- MNWFXJYAOYHMED-UHFFFAOYSA-N heptanoic acid Chemical compound CCCCCCC(O)=O MNWFXJYAOYHMED-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 229920003063 hydroxymethyl cellulose Polymers 0.000 description 1
- 229940031574 hydroxymethyl cellulose Drugs 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- NRXQIUSYPAHGNM-UHFFFAOYSA-N ioxynil Chemical compound OC1=C(I)C=C(C#N)C=C1I NRXQIUSYPAHGNM-UHFFFAOYSA-N 0.000 description 1
- 238000003973 irrigation Methods 0.000 description 1
- 230000002262 irrigation Effects 0.000 description 1
- PUIYMUZLKQOUOZ-UHFFFAOYSA-N isoproturon Chemical compound CC(C)C1=CC=C(NC(=O)N(C)C)C=C1 PUIYMUZLKQOUOZ-UHFFFAOYSA-N 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 229960002900 methylcellulose Drugs 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- RSMUVYRMZCOLBH-UHFFFAOYSA-N metsulfuron methyl Chemical group COC(=O)C1=CC=CC=C1S(=O)(=O)NC(=O)NC1=NC(C)=NC(OC)=N1 RSMUVYRMZCOLBH-UHFFFAOYSA-N 0.000 description 1
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 229940049964 oleate Drugs 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 239000003209 petroleum derivative Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- 229920001983 poloxamer Polymers 0.000 description 1
- 229920000233 poly(alkylene oxides) Polymers 0.000 description 1
- 229920001281 polyalkylene Chemical class 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 235000019422 polyvinyl alcohol Nutrition 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 239000003352 sequestering agent Substances 0.000 description 1
- 238000013207 serial dilution Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 238000001694 spray drying Methods 0.000 description 1
- 238000003892 spreading Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000008399 tap water Substances 0.000 description 1
- 235000020679 tap water Nutrition 0.000 description 1
- IROINLKCQGIITA-UHFFFAOYSA-N terbutryn Chemical compound CCNC1=NC(NC(C)(C)C)=NC(SC)=N1 IROINLKCQGIITA-UHFFFAOYSA-N 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
- 238000005809 transesterification reaction Methods 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
- 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
- 229940087291 tridecyl alcohol Drugs 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 229920003169 water-soluble polymer Polymers 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000000230 xanthan gum Substances 0.000 description 1
- 229920001285 xanthan gum Polymers 0.000 description 1
- 235000010493 xanthan gum Nutrition 0.000 description 1
- 229940082509 xanthan gum Drugs 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/72—Nitrogen atoms
- C07D213/73—Unsubstituted amino or imino radicals
-
- 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
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Processing Of Solid Wastes (AREA)
- Catching Or Destruction (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US08/052,446 US5374603A (en) | 1993-04-23 | 1993-04-23 | Agricultural formulations comprising fluroxypyr esters which are liquid at 25° C. |
| PCT/US1994/003880 WO1994024866A1 (en) | 1993-04-23 | 1994-04-08 | Agricultural formulations |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE69412200D1 DE69412200D1 (de) | 1998-09-10 |
| DE69412200T2 true DE69412200T2 (de) | 1998-12-10 |
Family
ID=21977661
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE69412200T Expired - Fee Related DE69412200T2 (de) | 1993-04-23 | 1994-04-08 | Landwirtschaftliche formulierungen enthaltend flüssige estern von fluroxypyr |
Country Status (24)
Families Citing this family (26)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9505204D0 (en) * | 1995-03-15 | 1995-05-03 | Dowelanco | Mixed herbicidal compositions |
| US5965487A (en) * | 1995-03-15 | 1999-10-12 | Dow Agrosciences Llc | Mixed herbicidal compositions |
| US5834400A (en) * | 1997-04-29 | 1998-11-10 | Isp Investments Inc. | Emulsifiable concentrate for a low dosage fluorinated agricultural chemical |
| US6566308B1 (en) * | 1999-01-29 | 2003-05-20 | Basf Aktiengesellschaft | Emulsifiable concentrate containing one or more pesticides and adjuvants |
| US6825151B2 (en) * | 2002-01-30 | 2004-11-30 | Nufarm Americas Inc. | Liquid herbicidal compositions and use thereof in a granular herbicide |
| DE10209478A1 (de) * | 2002-03-05 | 2003-09-18 | Bayer Cropscience Gmbh | Herbizid-Kombinationen mit speziellen Sulfonylharnstoffen |
| US20050026781A1 (en) * | 2003-04-22 | 2005-02-03 | Monsanto Technology Llc | Herbicidal compositions containing glyphosate and a pyridine analog |
| CN1960634A (zh) | 2004-03-10 | 2007-05-09 | 孟山都技术公司 | 含有n－膦酰基甲基甘氨酸和茁长素除草剂的除草剂组合物 |
| MY141272A (en) * | 2006-06-29 | 2010-04-16 | Dow Agrosciences Llc | High-strength, low-temperature stable herbicidal formulations of fluroxypyr esters |
| JP5125126B2 (ja) * | 2007-01-31 | 2013-01-23 | 住友化学株式会社 | 疎水性農薬活性化合物を含有する農薬液剤 |
| BRPI0813975B8 (pt) * | 2007-08-22 | 2022-06-28 | Dow Agrosciences Llc | Formulações de éster fluroxipir meptílico herbicidas estáveis sob baixa temperatura de alta resistência. |
| JP5256749B2 (ja) * | 2008-01-23 | 2013-08-07 | 住友化学株式会社 | 乳剤組成物 |
| JP2009173578A (ja) * | 2008-01-24 | 2009-08-06 | Sumitomo Chemical Co Ltd | 乳剤組成物 |
| JP5262131B2 (ja) * | 2008-01-24 | 2013-08-14 | 住友化学株式会社 | 乳剤組成物 |
| WO2009100101A2 (en) * | 2008-02-05 | 2009-08-13 | Arysta Lifescience North America, Llc | Solid formulation of low melting active compound |
| MY158051A (en) * | 2008-10-29 | 2016-08-30 | Dow Agrosciences Llc | Stable emulsifiable concentrates containing a first herbicidal carboxylic acid salt and a second herbicidal carboxylic acid ester |
| CA2785654C (en) * | 2009-12-29 | 2018-02-27 | Syngenta Participations Ag | Pesticidal composition |
| 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 |
| AR091268A1 (es) | 2012-06-04 | 2015-01-21 | Monsanto Technology Llc | Composiciones herbicidas concentradas acuosas que contienen sales de glifosato y sales de dicamba |
| RU2668850C2 (ru) * | 2012-12-20 | 2018-10-03 | ДАУ АГРОСАЙЕНСИЗ ЭлЭлСи | Гербицидные композиции, содержащие флуроксипир и флуметсулам |
| CA3123572A1 (en) | 2013-02-27 | 2014-09-04 | Monsanto Technology Llc | Glyphosate composition for dicamba tank mixtures with improved volatility |
| CN108347944B (zh) | 2015-10-26 | 2021-09-03 | 美国陶氏益农公司 | 含有氟氯比的固态除草剂组合物 |
| US20240067759A1 (en) | 2021-01-13 | 2024-02-29 | Nutrition & Biosciences Usa 1, Llc | Improved method for the preparation of colloidal microcrystalline cellulose |
| WO2022194371A1 (en) | 2021-03-17 | 2022-09-22 | Globachem Nv | Herbicidal compositions of fluroxypyr |
| US20250059302A1 (en) | 2021-12-14 | 2025-02-20 | Nutrition & Biosciences Usa 1, Llc | Process for reducing nitrite in microcrystalline cellulose |
| US11999684B1 (en) * | 2023-10-09 | 2024-06-04 | King Faisal University | Ethyl {[N'-(3-chlorophenyl)-N-(2,4-dichlorobenzoyl) carbamimidoyl]sulfanyl}acetate as an eco-friendly insecticidal agent against Spodoptera littoralis (boisd.) |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3755339A (en) * | 1971-07-26 | 1973-08-28 | Dow Chemical Co | Esters of aminohalopyridyloxy acids |
| US4108629A (en) * | 1973-03-19 | 1978-08-22 | The Dow Chemical Company | Herbicidal use of esters of aminohalopyridyloxy acids |
| US4542221A (en) * | 1981-05-18 | 1985-09-17 | The Dow Chemical Company | Exchanging fluorine for chlorine in a chlorinated pyridine with an alkali metal fluoride |
| GB2100128B (en) * | 1981-06-15 | 1984-08-08 | Dow Chemical Co | A herbicidal composition |
| GB2100129B (en) * | 1981-06-15 | 1984-08-30 | Dow Chemical Co | Composition for a herbicide |
| GB8304829D0 (en) * | 1983-02-22 | 1983-03-23 | Fbc Ltd | Herbicide |
| EP0441459A1 (en) * | 1985-07-02 | 1991-08-14 | Pioneer Electronic Corporation | Pulse-width modulation drive circuit |
| DE3883251D1 (de) * | 1987-10-14 | 1993-09-16 | Dowelanco | Latex enthaltende agrochemische zusammensetzungen. |
| BR9100532A (pt) * | 1990-02-09 | 1991-10-29 | Dowelanco | Processo para a preparacao de um ester de acido(4-amino-3,5-dicloro-6-fluoro-2-piridimilox)acetico e um alcool alifatico |
| GB9109600D0 (en) * | 1991-05-03 | 1991-06-26 | Dow Chemical Co | Synergistic herbicidal compositions |
-
1993
- 1993-04-23 US US08/052,446 patent/US5374603A/en not_active Expired - Fee Related
- 1993-08-18 TW TW082106650A patent/TW272932B/zh active
- 1993-08-26 CO CO93404646A patent/CO4560532A1/es unknown
-
1994
- 1994-04-08 DK DK94913390T patent/DK0647096T3/da active
- 1994-04-08 CN CN94190218A patent/CN1068171C/zh not_active Expired - Fee Related
- 1994-04-08 JP JP6524295A patent/JPH08501320A/ja not_active Ceased
- 1994-04-08 WO PCT/US1994/003880 patent/WO1994024866A1/en active IP Right Grant
- 1994-04-08 EP EP94913390A patent/EP0647096B1/en not_active Expired - Lifetime
- 1994-04-08 BR BR9405242-5A patent/BR9405242A/pt not_active Application Discontinuation
- 1994-04-08 CZ CZ19943283A patent/CZ287100B6/cs not_active IP Right Cessation
- 1994-04-08 KR KR1019940704681A patent/KR100232246B1/ko not_active Expired - Fee Related
- 1994-04-08 RO RO94-02086A patent/RO112425B1/ro unknown
- 1994-04-08 AU AU65569/94A patent/AU668472B2/en not_active Ceased
- 1994-04-08 CA CA002138965A patent/CA2138965A1/en not_active Abandoned
- 1994-04-08 PL PL94306837A patent/PL177145B1/pl unknown
- 1994-04-08 ES ES94913390T patent/ES2122268T3/es not_active Expired - Lifetime
- 1994-04-08 RU RU95105586A patent/RU2139659C1/ru active
- 1994-04-08 DE DE69412200T patent/DE69412200T2/de not_active Expired - Fee Related
- 1994-04-08 HU HU9403753A patent/HU217371B/hu not_active IP Right Cessation
- 1994-04-21 MY MYPI94000985A patent/MY110710A/en unknown
- 1994-04-21 IL IL109362A patent/IL109362A/en not_active IP Right Cessation
- 1994-04-22 ZA ZA942814A patent/ZA942814B/xx unknown
- 1994-04-26 US US08/233,207 patent/US5436223A/en not_active Expired - Fee Related
- 1994-08-04 UA UA95018061A patent/UA39874C2/uk unknown
- 1994-12-22 FI FI946037A patent/FI107012B/fi active
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| Date | Code | Title | Description |
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| 8364 | No opposition during term of opposition | ||
| 8327 | Change in the person/name/address of the patent owner |
Owner name: DOW AGROSCIENCES LLC, INDIANAPOLIS, IND., US |
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| 8339 | Ceased/non-payment of the annual fee |