PL177145B1 - Preparat rolniczy oraz sposób zwalczania niepożądanej roślinności - Google Patents
Preparat rolniczy oraz sposób zwalczania niepożądanej roślinnościInfo
- Publication number
- PL177145B1 PL177145B1 PL94306837A PL30683794A PL177145B1 PL 177145 B1 PL177145 B1 PL 177145B1 PL 94306837 A PL94306837 A PL 94306837A PL 30683794 A PL30683794 A PL 30683794A PL 177145 B1 PL177145 B1 PL 177145B1
- Authority
- PL
- Poland
- Prior art keywords
- ester
- fluroxypyr
- formulations
- butoxy
- preparation
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 title claims description 58
- 239000000203 mixture Substances 0.000 claims abstract description 99
- 238000009472 formulation Methods 0.000 claims abstract description 76
- -1 1-butoxy-2-propyl Chemical group 0.000 claims abstract description 73
- 239000005558 Fluroxypyr Substances 0.000 claims abstract description 61
- MEFQWPUMEMWTJP-UHFFFAOYSA-N fluroxypyr Chemical compound NC1=C(Cl)C(F)=NC(OCC(O)=O)=C1Cl MEFQWPUMEMWTJP-UHFFFAOYSA-N 0.000 claims abstract description 47
- 150000002148 esters Chemical class 0.000 claims abstract description 40
- 239000007788 liquid Substances 0.000 claims abstract description 25
- 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 abstract description 8
- 239000004808 2-ethylhexylester Substances 0.000 claims abstract description 8
- 239000000839 emulsion Substances 0.000 claims description 30
- 239000004495 emulsifiable concentrate Substances 0.000 claims description 25
- 238000000034 method Methods 0.000 claims description 22
- 239000004563 wettable powder Substances 0.000 claims description 20
- 239000004562 water dispersible granule Substances 0.000 claims description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 13
- 238000007865 diluting Methods 0.000 claims description 4
- 239000004009 herbicide Substances 0.000 abstract description 18
- 239000003960 organic solvent Substances 0.000 abstract description 8
- 230000000704 physical effect Effects 0.000 abstract description 4
- 239000002253 acid Substances 0.000 description 29
- 239000002904 solvent Substances 0.000 description 25
- 230000002363 herbicidal effect Effects 0.000 description 23
- 239000004094 surface-active agent Substances 0.000 description 23
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 21
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 14
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 13
- 239000000377 silicon dioxide Substances 0.000 description 10
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 9
- 239000002736 nonionic surfactant Substances 0.000 description 9
- 239000012071 phase Substances 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- 230000000694 effects Effects 0.000 description 8
- 239000004480 active ingredient Substances 0.000 description 7
- 239000002563 ionic surfactant Substances 0.000 description 6
- 230000008014 freezing Effects 0.000 description 5
- 238000007710 freezing Methods 0.000 description 5
- 230000005484 gravity Effects 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 238000009736 wetting Methods 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 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
- 239000002270 dispersing agent Substances 0.000 description 4
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N isopropyl alcohol Natural products CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 229920000847 nonoxynol Polymers 0.000 description 4
- 229920002451 polyvinyl alcohol Polymers 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 239000000080 wetting agent Substances 0.000 description 4
- GZEYORSRDNLAPB-UHFFFAOYSA-N 1-butoxybutan-2-ol Chemical compound CCCCOCC(O)CC GZEYORSRDNLAPB-UHFFFAOYSA-N 0.000 description 3
- 229920005682 EO-PO block copolymer Polymers 0.000 description 3
- 241000196324 Embryophyta Species 0.000 description 3
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 3
- 239000002671 adjuvant Substances 0.000 description 3
- 239000012736 aqueous medium Substances 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 239000012141 concentrate Substances 0.000 description 3
- UQDUPQYQJKYHQI-UHFFFAOYSA-N dodecanoic acid methyl ester Natural products CCCCCCCCCCCC(=O)OC UQDUPQYQJKYHQI-UHFFFAOYSA-N 0.000 description 3
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- 239000003208 petroleum Substances 0.000 description 3
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- 238000003756 stirring Methods 0.000 description 3
- CUVLMZNMSPJDON-UHFFFAOYSA-N 1-(1-butoxypropan-2-yloxy)propan-2-ol Chemical compound CCCCOCC(C)OCC(C)O CUVLMZNMSPJDON-UHFFFAOYSA-N 0.000 description 2
- RWNUSVWFHDHRCJ-UHFFFAOYSA-N 1-butoxypropan-2-ol Chemical compound CCCCOCC(C)O RWNUSVWFHDHRCJ-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
- 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 2
- UDXVMLIGVOVHGW-UHFFFAOYSA-N 7,10-dioxadispiro[2.2.4^{6}.2^{3}]dodecane Chemical compound C1CC11CCC2(OCCO2)CC1 UDXVMLIGVOVHGW-UHFFFAOYSA-N 0.000 description 2
- 239000005995 Aluminium silicate Substances 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
- 239000005582 Metosulam Substances 0.000 description 2
- VGHPMIFEKOFHHQ-UHFFFAOYSA-N Metosulam Chemical compound N1=C2N=C(OC)C=C(OC)N2N=C1S(=O)(=O)NC1=C(Cl)C=CC(C)=C1Cl VGHPMIFEKOFHHQ-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
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 150000004996 alkyl benzenes Chemical class 0.000 description 2
- 235000012211 aluminium silicate Nutrition 0.000 description 2
- 239000003945 anionic surfactant Substances 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 229940092714 benzenesulfonic acid Drugs 0.000 description 2
- 229920001400 block copolymer Polymers 0.000 description 2
- 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 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
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 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
- 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
- 239000002245 particle Substances 0.000 description 2
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- 235000015112 vegetable and seed oil Nutrition 0.000 description 2
- 239000008158 vegetable oil Substances 0.000 description 2
- JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical class OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-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
- ZZMSHBOVYPIYOB-UHFFFAOYSA-N 1,4-diphenylpyrazolidine-3,5-dione Chemical compound O=C1NN(C=2C=CC=CC=2)C(=O)C1C1=CC=CC=C1 ZZMSHBOVYPIYOB-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
- ZKFARSBUEBZZJT-UHFFFAOYSA-N 1-butoxypropan-2-yl 2-(4-amino-3,5-dichloro-6-fluoropyridin-2-yl)oxyacetate Chemical compound CCCCOCC(C)OC(=O)COC1=NC(F)=C(Cl)C(N)=C1Cl ZKFARSBUEBZZJT-UHFFFAOYSA-N 0.000 description 1
- FUWDFGKRNIDKAE-UHFFFAOYSA-N 1-butoxypropan-2-yl acetate Chemical compound CCCCOCC(C)OC(C)=O FUWDFGKRNIDKAE-UHFFFAOYSA-N 0.000 description 1
- CXBDYQVECUFKRK-UHFFFAOYSA-N 1-methoxybutane Chemical compound CCCCOC CXBDYQVECUFKRK-UHFFFAOYSA-N 0.000 description 1
- 239000005631 2,4-Dichlorophenoxyacetic acid Substances 0.000 description 1
- QWYOHSSQBJOUOY-UHFFFAOYSA-N 2-(2-hydroxyethylamino)ethanol octadecane-1-sulfonic acid Chemical class OCCNCCO.CCCCCCCCCCCCCCCCCCS(O)(=O)=O QWYOHSSQBJOUOY-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
- 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
- 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 1
- RFVNOJDQRGSOEL-UHFFFAOYSA-N 2-hydroxyethyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCCO RFVNOJDQRGSOEL-UHFFFAOYSA-N 0.000 description 1
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- CTTHWASMBLQOFR-UHFFFAOYSA-N Amidosulfuron Chemical compound COC1=CC(OC)=NC(NC(=O)NS(=O)(=O)N(C)S(C)(=O)=O)=N1 CTTHWASMBLQOFR-UHFFFAOYSA-N 0.000 description 1
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- 101000742062 Bos taurus Protein phosphatase 1G Proteins 0.000 description 1
- XTFNPKDYCLFGPV-OMCISZLKSA-N Bromofenoxim Chemical compound C1=C(Br)C(O)=C(Br)C=C1\C=N\OC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O XTFNPKDYCLFGPV-OMCISZLKSA-N 0.000 description 1
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- 229960002154 guar gum Drugs 0.000 description 1
- 238000003306 harvesting Methods 0.000 description 1
- 231100001261 hazardous Toxicity 0.000 description 1
- MNWFXJYAOYHMED-UHFFFAOYSA-N heptanoic acid Chemical compound CCCCCCC(O)=O MNWFXJYAOYHMED-UHFFFAOYSA-N 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000008240 homogeneous mixture Substances 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
- 229940070765 laurate Drugs 0.000 description 1
- 239000012669 liquid formulation Substances 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
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 229960002900 methylcellulose Drugs 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
- 239000007764 o/w emulsion Substances 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- 229920001983 poloxamer 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
- 230000008092 positive effect Effects 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
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 239000003352 sequestering agent Substances 0.000 description 1
- 238000013207 serial dilution Methods 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229950004959 sorbitan oleate Drugs 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 238000001694 spray drying Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000003892 spreading Methods 0.000 description 1
- 238000007619 statistical method 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
- 239000000375 suspending agent Substances 0.000 description 1
- 239000008399 tap water Substances 0.000 description 1
- 235000020679 tap water Nutrition 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
- 239000003643 water by type Substances 0.000 description 1
- 229920003169 water-soluble polymer Polymers 0.000 description 1
- 239000000230 xanthan gum Substances 0.000 description 1
- 235000010493 xanthan gum Nutrition 0.000 description 1
- 229920001285 xanthan gum Polymers 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)
- Dentistry (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Agronomy & Crop Science (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 |
|---|---|
| PL306837A1 PL306837A1 (en) | 1995-04-18 |
| PL177145B1 true PL177145B1 (pl) | 1999-09-30 |
Family
ID=21977661
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL94306837A PL177145B1 (pl) | 1993-04-23 | 1994-04-08 | Preparat rolniczy oraz sposób zwalczania niepożądanej roślinności |
Country Status (24)
| Country | Link |
|---|---|
| US (2) | US5374603A (forum.php) |
| EP (1) | EP0647096B1 (forum.php) |
| JP (1) | JPH08501320A (forum.php) |
| KR (1) | KR100232246B1 (forum.php) |
| CN (1) | CN1068171C (forum.php) |
| AU (1) | AU668472B2 (forum.php) |
| BR (1) | BR9405242A (forum.php) |
| CA (1) | CA2138965A1 (forum.php) |
| CO (1) | CO4560532A1 (forum.php) |
| CZ (1) | CZ287100B6 (forum.php) |
| DE (1) | DE69412200T2 (forum.php) |
| DK (1) | DK0647096T3 (forum.php) |
| ES (1) | ES2122268T3 (forum.php) |
| FI (1) | FI107012B (forum.php) |
| HU (1) | HU217371B (forum.php) |
| IL (1) | IL109362A (forum.php) |
| MY (1) | MY110710A (forum.php) |
| PL (1) | PL177145B1 (forum.php) |
| RO (1) | RO112425B1 (forum.php) |
| RU (1) | RU2139659C1 (forum.php) |
| TW (1) | TW272932B (forum.php) |
| UA (1) | UA39874C2 (forum.php) |
| WO (1) | WO1994024866A1 (forum.php) |
| ZA (1) | ZA942814B (forum.php) |
Families Citing this family (26)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5965487A (en) * | 1995-03-15 | 1999-10-12 | Dow Agrosciences Llc | Mixed herbicidal compositions |
| GB9505204D0 (en) * | 1995-03-15 | 1995-05-03 | Dowelanco | 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 |
| CA2558642C (en) | 2004-03-10 | 2017-08-08 | Monsanto Technology Llc | Herbicidal compositions containing n-phosphonomethyl glycine and an auxin herbicide |
| 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 |
| AU2009212525B2 (en) * | 2008-02-05 | 2012-06-21 | Arysta Lifescience North America, Llc | Solid formulation of low melting active compound |
| PL2361012T3 (pl) * | 2008-10-29 | 2016-11-30 | Stabilne emulgowalne koncentraty zawierające pierwszą chwastobójczą sól kwasu karboksylowego oraz drugi chwastobójczy ester kwasu karboksylowego | |
| WO2011082162A1 (en) * | 2009-12-29 | 2011-07-07 | Syngenta Participations Ag | Pesticidal composition |
| US10334849B2 (en) | 2011-10-26 | 2019-07-02 | Monsanto Technology Llc | Salts of carboxylic acid herbicides |
| 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 |
| PL2961276T3 (pl) | 2013-02-27 | 2019-01-31 | Monsanto Technology Llc | Mieszanki zbiornikowe zawierające sól glifosatu i sól dikamby o poprawionej lotności |
| IL258871B2 (en) * | 2015-10-26 | 2025-03-01 | Corteva Agriscience Llc | Solid herbicide preparations containing fluroxypyr-meptyl |
| BR112023013931A2 (pt) | 2021-01-13 | 2024-01-23 | Nutrition & Biosciences Usa 1 Llc | Método aprimorado para a preparação de celulose microcristalina coloidal |
| EP4307890A1 (en) | 2021-03-17 | 2024-01-24 | Globachem NV | Herbicidal compositions of fluroxypyr |
| CN118541430A (zh) | 2021-12-14 | 2024-08-23 | 营养与生物科学美国1有限责任公司 | 用于减少微晶纤维素中的亚硝酸盐的方法 |
| 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 |
| EP0381691B1 (en) * | 1987-10-14 | 1992-10-07 | Dowelanco | Latex-based agricultural compositions |
| 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 RO RO94-02086A patent/RO112425B1/ro unknown
- 1994-04-08 DE DE69412200T patent/DE69412200T2/de not_active Expired - Fee Related
- 1994-04-08 EP EP94913390A patent/EP0647096B1/en not_active Expired - Lifetime
- 1994-04-08 CA CA002138965A patent/CA2138965A1/en not_active Abandoned
- 1994-04-08 BR BR9405242-5A patent/BR9405242A/pt not_active Application Discontinuation
- 1994-04-08 PL PL94306837A patent/PL177145B1/pl unknown
- 1994-04-08 WO PCT/US1994/003880 patent/WO1994024866A1/en not_active Ceased
- 1994-04-08 DK DK94913390T patent/DK0647096T3/da active
- 1994-04-08 HU HU9403753A patent/HU217371B/hu not_active IP Right Cessation
- 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 AU AU65569/94A patent/AU668472B2/en not_active Ceased
- 1994-04-08 RU RU95105586A patent/RU2139659C1/ru active
- 1994-04-08 KR KR1019940704681A patent/KR100232246B1/ko not_active Expired - Fee Related
- 1994-04-08 CZ CZ19943283A patent/CZ287100B6/cs not_active IP Right Cessation
- 1994-04-08 ES ES94913390T patent/ES2122268T3/es not_active Expired - Lifetime
- 1994-04-21 IL IL109362A patent/IL109362A/en not_active IP Right Cessation
- 1994-04-21 MY MYPI94000985A patent/MY110710A/en unknown
- 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
Also Published As
| Publication number | Publication date |
|---|---|
| AU6556994A (en) | 1994-11-21 |
| PL306837A1 (en) | 1995-04-18 |
| US5374603A (en) | 1994-12-20 |
| EP0647096B1 (en) | 1998-08-05 |
| US5436223A (en) | 1995-07-25 |
| ZA942814B (en) | 1995-10-23 |
| RU2139659C1 (ru) | 1999-10-20 |
| CZ328394A3 (en) | 1995-07-12 |
| TW272932B (forum.php) | 1996-03-21 |
| HU217371B (hu) | 2000-01-28 |
| IL109362A0 (en) | 1994-07-31 |
| HUT69008A (en) | 1995-08-28 |
| EP0647096A1 (en) | 1995-04-12 |
| FI946037A0 (fi) | 1994-12-22 |
| KR100232246B1 (ko) | 1999-12-01 |
| DE69412200D1 (de) | 1998-09-10 |
| ES2122268T3 (es) | 1998-12-16 |
| UA39874C2 (uk) | 2001-07-16 |
| BR9405242A (pt) | 1999-08-31 |
| FI946037L (fi) | 1994-12-22 |
| IL109362A (en) | 1998-02-08 |
| CN1107273A (zh) | 1995-08-23 |
| CO4560532A1 (es) | 1998-02-10 |
| JPH08501320A (ja) | 1996-02-13 |
| DE69412200T2 (de) | 1998-12-10 |
| WO1994024866A1 (en) | 1994-11-10 |
| CN1068171C (zh) | 2001-07-11 |
| RU95105586A (ru) | 1996-10-27 |
| FI107012B (fi) | 2001-05-31 |
| DK0647096T3 (da) | 1999-05-10 |
| CA2138965A1 (en) | 1994-11-10 |
| RO112425B1 (ro) | 1997-09-30 |
| AU668472B2 (en) | 1996-05-02 |
| CZ287100B6 (en) | 2000-09-13 |
| MY110710A (en) | 1999-01-30 |
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