PT1947935E - Formulações líquidas de herbicida de sulfonilureia - Google Patents
Formulações líquidas de herbicida de sulfonilureia Download PDFInfo
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- PT1947935E PT1947935E PT06813996T PT06813996T PT1947935E PT 1947935 E PT1947935 E PT 1947935E PT 06813996 T PT06813996 T PT 06813996T PT 06813996 T PT06813996 T PT 06813996T PT 1947935 E PT1947935 E PT 1947935E
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- 239000000203 mixture Substances 0.000 title claims abstract description 201
- 229940100389 Sulfonylurea Drugs 0.000 title claims abstract description 71
- YROXIXLRRCOBKF-UHFFFAOYSA-N sulfonylurea Chemical class OC(=N)N=S(=O)=O YROXIXLRRCOBKF-UHFFFAOYSA-N 0.000 title claims abstract description 56
- 239000004009 herbicide Substances 0.000 title claims abstract description 54
- 230000002363 herbicidal effect Effects 0.000 title claims abstract description 20
- 239000007788 liquid Substances 0.000 title claims description 17
- 238000009472 formulation Methods 0.000 title claims description 13
- -1 fatty acid esters Chemical class 0.000 claims abstract description 91
- 235000014113 dietary fatty acids Nutrition 0.000 claims abstract description 61
- 239000000194 fatty acid Substances 0.000 claims abstract description 61
- 229930195729 fatty acid Natural products 0.000 claims abstract description 61
- 229920001732 Lignosulfonate Polymers 0.000 claims abstract description 43
- 239000004615 ingredient Substances 0.000 claims abstract description 21
- 239000007791 liquid phase Substances 0.000 claims abstract description 17
- 239000013543 active substance Substances 0.000 claims abstract description 9
- 239000005586 Nicosulfuron Substances 0.000 claims description 39
- RTCOGUMHFFWOJV-UHFFFAOYSA-N nicosulfuron Chemical compound COC1=CC(OC)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CN=2)C(=O)N(C)C)=N1 RTCOGUMHFFWOJV-UHFFFAOYSA-N 0.000 claims description 39
- 150000004665 fatty acids Chemical class 0.000 claims description 27
- 150000002148 esters Chemical class 0.000 claims description 20
- 239000004094 surface-active agent Substances 0.000 claims description 20
- 239000005616 Rimsulfuron Substances 0.000 claims description 19
- MEFOUWRMVYJCQC-UHFFFAOYSA-N rimsulfuron Chemical compound CCS(=O)(=O)C1=CC=CN=C1S(=O)(=O)NC(=O)NC1=NC(OC)=CC(OC)=N1 MEFOUWRMVYJCQC-UHFFFAOYSA-N 0.000 claims description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 18
- 150000003839 salts Chemical class 0.000 claims description 17
- 239000000126 substance Substances 0.000 claims description 16
- 239000004927 clay Substances 0.000 claims description 12
- 239000005584 Metsulfuron-methyl Substances 0.000 claims description 10
- 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 claims description 10
- JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Polymers OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 claims description 9
- JNYAEWCLZODPBN-UHFFFAOYSA-N 2-(1,2-dihydroxyethyl)oxolane-3,4-diol Polymers OCC(O)C1OCC(O)C1O JNYAEWCLZODPBN-UHFFFAOYSA-N 0.000 claims description 8
- JNYAEWCLZODPBN-CTQIIAAMSA-N sorbitan Polymers OCC(O)C1OCC(O)[C@@H]1O JNYAEWCLZODPBN-CTQIIAAMSA-N 0.000 claims description 8
- VJYIFXVZLXQVHO-UHFFFAOYSA-N chlorsulfuron Chemical compound COC1=NC(C)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)Cl)=N1 VJYIFXVZLXQVHO-UHFFFAOYSA-N 0.000 claims description 7
- 239000005623 Thifensulfuron-methyl Substances 0.000 claims description 6
- MXWJVTOOROXGIU-UHFFFAOYSA-N atrazine Chemical compound CCNC1=NC(Cl)=NC(NC(C)C)=N1 MXWJVTOOROXGIU-UHFFFAOYSA-N 0.000 claims description 6
- NSWAMPCUPHPTTC-UHFFFAOYSA-N chlorimuron-ethyl Chemical group CCOC(=O)C1=CC=CC=C1S(=O)(=O)NC(=O)NC1=NC(Cl)=CC(OC)=N1 NSWAMPCUPHPTTC-UHFFFAOYSA-N 0.000 claims description 6
- NIFKBBMCXCMCAO-UHFFFAOYSA-N methyl 2-[(4,6-dimethoxypyrimidin-2-yl)carbamoylsulfamoyl]-4-(methanesulfonamidomethyl)benzoate Chemical group COC(=O)C1=CC=C(CNS(C)(=O)=O)C=C1S(=O)(=O)NC(=O)NC1=NC(OC)=CC(OC)=N1 NIFKBBMCXCMCAO-UHFFFAOYSA-N 0.000 claims description 6
- AHTPATJNIAFOLR-UHFFFAOYSA-N thifensulfuron-methyl Chemical group S1C=CC(S(=O)(=O)NC(=O)NC=2N=C(OC)N=C(C)N=2)=C1C(=O)OC AHTPATJNIAFOLR-UHFFFAOYSA-N 0.000 claims description 6
- YMXOXAPKZDWXLY-QWRGUYRKSA-N tribenuron methyl Chemical group COC(=O)[C@H]1CCCC[C@@H]1S(=O)(=O)NC(=O)N(C)C1=NC(C)=NC(OC)=N1 YMXOXAPKZDWXLY-QWRGUYRKSA-N 0.000 claims description 6
- FBPFZTCFMRRESA-NQAPHZHOSA-N Sorbitol Polymers OCC(O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-NQAPHZHOSA-N 0.000 claims description 5
- MAHPNPYYQAIOJN-UHFFFAOYSA-N azimsulfuron Chemical compound COC1=CC(OC)=NC(NC(=O)NS(=O)(=O)C=2N(N=CC=2C2=NN(C)N=N2)C)=N1 MAHPNPYYQAIOJN-UHFFFAOYSA-N 0.000 claims description 5
- 239000005469 Azimsulfuron Substances 0.000 claims description 4
- UWVKRNOCDUPIDM-UHFFFAOYSA-N Ethoxysulfuron Chemical compound CCOC1=CC=CC=C1OS(=O)(=O)NC(=O)NC1=NC(OC)=CC(OC)=N1 UWVKRNOCDUPIDM-UHFFFAOYSA-N 0.000 claims description 4
- HWATZEJQIXKWQS-UHFFFAOYSA-N Flazasulfuron Chemical compound COC1=CC(OC)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CN=2)C(F)(F)F)=N1 HWATZEJQIXKWQS-UHFFFAOYSA-N 0.000 claims description 4
- 239000005534 Flupyrsulfuron-methyl Substances 0.000 claims description 4
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 4
- DTVOKYWXACGVGO-UHFFFAOYSA-N methyl 2-[(4,6-dimethoxypyrimidin-2-yl)carbamoylsulfamoyl]-6-(trifluoromethyl)pyridine-3-carboxylate Chemical group COC(=O)C1=CC=C(C(F)(F)F)N=C1S(=O)(=O)NC(=O)NC1=NC(OC)=CC(OC)=N1 DTVOKYWXACGVGO-UHFFFAOYSA-N 0.000 claims description 4
- 230000001681 protective effect Effects 0.000 claims description 4
- RBSXHDIPCIWOMG-UHFFFAOYSA-N 1-(4,6-dimethoxypyrimidin-2-yl)-3-(2-ethylsulfonylimidazo[1,2-a]pyridin-3-yl)sulfonylurea Chemical compound CCS(=O)(=O)C=1N=C2C=CC=CN2C=1S(=O)(=O)NC(=O)NC1=NC(OC)=CC(OC)=N1 RBSXHDIPCIWOMG-UHFFFAOYSA-N 0.000 claims description 3
- 239000003666 Amidosulfuron Substances 0.000 claims description 3
- 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 claims description 3
- 239000005472 Bensulfuron methyl Substances 0.000 claims description 3
- 239000005514 Flazasulfuron Substances 0.000 claims description 3
- 239000005619 Sulfosulfuron Substances 0.000 claims description 3
- XMQFTWRPUQYINF-UHFFFAOYSA-N bensulfuron-methyl Chemical group COC(=O)C1=CC=CC=C1CS(=O)(=O)NC(=O)NC1=NC(OC)=CC(OC)=N1 XMQFTWRPUQYINF-UHFFFAOYSA-N 0.000 claims description 3
- 150000004702 methyl esters Chemical class 0.000 claims description 3
- AIMMSOZBPYFASU-UHFFFAOYSA-N n-(4,6-dimethoxypyrimidin-2-yl)-n'-[3-(2,2,2-trifluoroethoxy)pyridin-1-ium-2-yl]sulfonylcarbamimidate Chemical compound COC1=CC(OC)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CN=2)OCC(F)(F)F)=N1 AIMMSOZBPYFASU-UHFFFAOYSA-N 0.000 claims description 3
- 239000000575 pesticide Substances 0.000 claims description 3
- 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 claims description 3
- IMEVJVISCHQJRM-UHFFFAOYSA-N triflusulfuron-methyl Chemical group COC(=O)C1=CC=CC(C)=C1S(=O)(=O)NC(=O)NC1=NC(OCC(F)(F)F)=NC(N(C)C)=N1 IMEVJVISCHQJRM-UHFFFAOYSA-N 0.000 claims description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 2
- OFSLKOLYLQSJPB-UHFFFAOYSA-N Cyclosulfamuron Chemical compound COC1=CC(OC)=NC(NC(=O)NS(=O)(=O)NC=2C(=CC=CC=2)C(=O)C2CC2)=N1 OFSLKOLYLQSJPB-UHFFFAOYSA-N 0.000 claims description 2
- 239000005629 Tritosulfuron Substances 0.000 claims description 2
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- 150000001340 alkali metals Chemical class 0.000 claims description 2
- CURLHBZYTFVCRG-UHFFFAOYSA-N butan-2-yl n-(3-chlorophenyl)carbamate Chemical compound CCC(C)OC(=O)NC1=CC=CC(Cl)=C1 CURLHBZYTFVCRG-UHFFFAOYSA-N 0.000 claims description 2
- 239000003599 detergent Substances 0.000 claims description 2
- 239000003995 emulsifying agent Substances 0.000 claims description 2
- 229920005552 sodium lignosulfonate Polymers 0.000 claims description 2
- KVEQCVKVIFQSGC-UHFFFAOYSA-N tritosulfuron Chemical compound FC(F)(F)C1=NC(OC)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)C(F)(F)F)=N1 KVEQCVKVIFQSGC-UHFFFAOYSA-N 0.000 claims description 2
- 239000002023 wood Substances 0.000 claims description 2
- 241001503485 Mammuthus Species 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 40
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 23
- 125000000217 alkyl group Chemical group 0.000 description 22
- 125000004432 carbon atom Chemical group C* 0.000 description 21
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- 238000000034 method Methods 0.000 description 18
- 239000003085 diluting agent Substances 0.000 description 16
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 16
- 125000003545 alkoxy group Chemical group 0.000 description 15
- 239000007787 solid Substances 0.000 description 15
- RKZXQQPEDGMHBJ-LIGJGSPWSA-N [(2s,3r,4r,5r)-2,3,4,5,6-pentakis[[(z)-octadec-9-enoyl]oxy]hexyl] (z)-octadec-9-enoate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC[C@@H](OC(=O)CCCCCCC\C=C/CCCCCCCC)[C@@H](OC(=O)CCCCCCC\C=C/CCCCCCCC)[C@H](OC(=O)CCCCCCC\C=C/CCCCCCCC)[C@@H](OC(=O)CCCCCCC\C=C/CCCCCCCC)COC(=O)CCCCCCC\C=C/CCCCCCCC RKZXQQPEDGMHBJ-LIGJGSPWSA-N 0.000 description 12
- 239000000460 chlorine Substances 0.000 description 12
- 239000002253 acid Substances 0.000 description 11
- 229920000136 polysorbate Polymers 0.000 description 11
- 125000000714 pyrimidinyl group Chemical group 0.000 description 11
- 229910052801 chlorine Inorganic materials 0.000 description 10
- 238000000354 decomposition reaction Methods 0.000 description 10
- 235000019387 fatty acid methyl ester Nutrition 0.000 description 10
- 229910052731 fluorine Inorganic materials 0.000 description 10
- 238000004128 high performance liquid chromatography Methods 0.000 description 10
- 229910052739 hydrogen Inorganic materials 0.000 description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 10
- PRXRUNOAOLTIEF-ADSICKODSA-N Sorbitan trioleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC[C@@H](OC(=O)CCCCCCC\C=C/CCCCCCCC)[C@H]1OC[C@H](O)[C@H]1OC(=O)CCCCCCC\C=C/CCCCCCCC PRXRUNOAOLTIEF-ADSICKODSA-N 0.000 description 9
- 229910052794 bromium Inorganic materials 0.000 description 9
- 229910052799 carbon Inorganic materials 0.000 description 9
- 230000008569 process Effects 0.000 description 9
- 230000032683 aging Effects 0.000 description 8
- 239000011521 glass Substances 0.000 description 8
- 239000012669 liquid formulation Substances 0.000 description 8
- 239000002736 nonionic surfactant Substances 0.000 description 8
- 239000003549 soybean oil Substances 0.000 description 8
- 241000196324 Embryophyta Species 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 7
- 239000004147 Sorbitan trioleate Substances 0.000 description 7
- 238000010411 cooking Methods 0.000 description 7
- 150000002430 hydrocarbons Chemical group 0.000 description 7
- 229920006395 saturated elastomer Polymers 0.000 description 7
- 235000019337 sorbitan trioleate Nutrition 0.000 description 7
- 229960000391 sorbitan trioleate Drugs 0.000 description 7
- 238000006277 sulfonation reaction Methods 0.000 description 7
- 235000015112 vegetable and seed oil Nutrition 0.000 description 7
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 6
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Polymers OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 6
- 244000068988 Glycine max Species 0.000 description 6
- 235000010469 Glycine max Nutrition 0.000 description 6
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 6
- 229910052736 halogen Inorganic materials 0.000 description 6
- 150000002367 halogens Chemical class 0.000 description 6
- 239000002245 particle Substances 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- 229910052708 sodium Inorganic materials 0.000 description 6
- 239000011734 sodium Substances 0.000 description 6
- 235000012424 soybean oil Nutrition 0.000 description 6
- 239000000725 suspension Substances 0.000 description 6
- 239000004546 suspension concentrate Substances 0.000 description 6
- 239000005496 Chlorsulfuron Substances 0.000 description 5
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 5
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 5
- 239000004480 active ingredient Substances 0.000 description 5
- 239000011575 calcium Substances 0.000 description 5
- 229910052791 calcium Inorganic materials 0.000 description 5
- 235000001465 calcium Nutrition 0.000 description 5
- 239000000969 carrier Substances 0.000 description 5
- 125000001188 haloalkyl group Chemical group 0.000 description 5
- 229920005611 kraft lignin Polymers 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 229920000642 polymer Polymers 0.000 description 5
- 229910052700 potassium Inorganic materials 0.000 description 5
- 239000011591 potassium Substances 0.000 description 5
- 230000002441 reversible effect Effects 0.000 description 5
- 150000003384 small molecules Chemical class 0.000 description 5
- 159000000000 sodium salts Chemical class 0.000 description 5
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 description 5
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 description 4
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 125000004414 alkyl thio group Chemical group 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 239000006185 dispersion Substances 0.000 description 4
- 239000002655 kraft paper Substances 0.000 description 4
- 229920005610 lignin Polymers 0.000 description 4
- 229910052749 magnesium Inorganic materials 0.000 description 4
- 239000011777 magnesium Substances 0.000 description 4
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- 235000000346 sugar Nutrition 0.000 description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 4
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 description 3
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 3
- KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 description 3
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- WMLPCIHUFDKWJU-UHFFFAOYSA-N Cinosulfuron Chemical compound COCCOC1=CC=CC=C1S(=O)(=O)NC(=O)NC1=NC(OC)=NC(OC)=N1 WMLPCIHUFDKWJU-UHFFFAOYSA-N 0.000 description 3
- 229920000742 Cotton Polymers 0.000 description 3
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 244000299507 Gossypium hirsutum Species 0.000 description 3
- 244000020551 Helianthus annuus Species 0.000 description 3
- 235000003222 Helianthus annuus Nutrition 0.000 description 3
- 239000004165 Methyl ester of fatty acids Substances 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 229920001214 Polysorbate 60 Polymers 0.000 description 3
- LTUNNEGNEKBSEH-UHFFFAOYSA-N Prosulfuron Chemical compound COC1=NC(C)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)CCC(F)(F)F)=N1 LTUNNEGNEKBSEH-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 125000003342 alkenyl group Chemical group 0.000 description 3
- 125000003302 alkenyloxy group Chemical group 0.000 description 3
- 125000005133 alkynyloxy group Chemical group 0.000 description 3
- 125000000129 anionic group Chemical group 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000012141 concentrate Substances 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- 230000032050 esterification Effects 0.000 description 3
- 238000005886 esterification reaction Methods 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 125000004995 haloalkylthio group Chemical group 0.000 description 3
- 239000002917 insecticide Substances 0.000 description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 3
- 239000004005 microsphere Substances 0.000 description 3
- 239000000600 sorbitol Substances 0.000 description 3
- 239000012258 stirred mixture Substances 0.000 description 3
- 238000006467 substitution reaction Methods 0.000 description 3
- 150000008163 sugars Chemical class 0.000 description 3
- 238000005809 transesterification reaction Methods 0.000 description 3
- 125000006559 (C1-C3) alkylamino group Chemical group 0.000 description 2
- 125000004793 2,2,2-trifluoroethoxy group Chemical group FC(CO*)(F)F 0.000 description 2
- NUPJIGQFXCQJBK-UHFFFAOYSA-N 2-(4-isopropyl-4-methyl-5-oxo-4,5-dihydro-1H-imidazol-2-yl)-5-(methoxymethyl)nicotinic acid Chemical compound OC(=O)C1=CC(COC)=CN=C1C1=NC(C)(C(C)C)C(=O)N1 NUPJIGQFXCQJBK-UHFFFAOYSA-N 0.000 description 2
- CLQMBPJKHLGMQK-UHFFFAOYSA-N 2-(4-isopropyl-4-methyl-5-oxo-4,5-dihydro-1H-imidazol-2-yl)nicotinic acid Chemical compound N1C(=O)C(C(C)C)(C)N=C1C1=NC=CC=C1C(O)=O CLQMBPJKHLGMQK-UHFFFAOYSA-N 0.000 description 2
- 108010000700 Acetolactate synthase Proteins 0.000 description 2
- 229910002016 Aerosil® 200 Inorganic materials 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- OFDYMSKSGFSLLM-UHFFFAOYSA-N Dinitramine Chemical compound CCN(CC)C1=C([N+]([O-])=O)C=C(C(F)(F)F)C(N)=C1[N+]([O-])=O OFDYMSKSGFSLLM-UHFFFAOYSA-N 0.000 description 2
- FICWGWVVIRLNRB-UHFFFAOYSA-N Flucetosulfuron Chemical compound COCC(=O)OC(C(C)F)C1=NC=CC=C1S(=O)(=O)NC(=O)NC1=NC(OC)=CC(OC)=N1 FICWGWVVIRLNRB-UHFFFAOYSA-N 0.000 description 2
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- APTZNLHMIGJTEW-UHFFFAOYSA-N pyraflufen-ethyl Chemical group C1=C(Cl)C(OCC(=O)OCC)=CC(C=2C(=C(OC(F)F)N(C)N=2)Cl)=C1F APTZNLHMIGJTEW-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- NKFLEFWUYAUDJV-UHFFFAOYSA-N pyridine-3-sulfonamide Chemical compound NS(=O)(=O)C1=CC=CN=C1 NKFLEFWUYAUDJV-UHFFFAOYSA-N 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- BACHBFVBHLGWSL-JTQLQIEISA-N rac-diclofop methyl Natural products C1=CC(O[C@@H](C)C(=O)OC)=CC=C1OC1=CC=C(Cl)C=C1Cl BACHBFVBHLGWSL-JTQLQIEISA-N 0.000 description 1
- 239000010499 rapseed oil Substances 0.000 description 1
- 230000008707 rearrangement Effects 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 239000006254 rheological additive Substances 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 150000004671 saturated fatty acids Chemical class 0.000 description 1
- 238000004062 sedimentation Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 235000015424 sodium Nutrition 0.000 description 1
- WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 1
- 239000004299 sodium benzoate Substances 0.000 description 1
- 235000010234 sodium benzoate Nutrition 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M sodium chloride Inorganic materials [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 1
- 239000008247 solid mixture Substances 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000004334 sorbic acid Substances 0.000 description 1
- 235000010199 sorbic acid Nutrition 0.000 description 1
- 229940075582 sorbic acid Drugs 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 125000005750 substituted cyclic group Chemical group 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
- ZDXMLEQEMNLCQG-UHFFFAOYSA-N sulfometuron methyl Chemical group COC(=O)C1=CC=CC=C1S(=O)(=O)NC(=O)NC1=NC(C)=CC(C)=N1 ZDXMLEQEMNLCQG-UHFFFAOYSA-N 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 239000004557 technical material Substances 0.000 description 1
- IUQAXCIUEPFPSF-UHFFFAOYSA-N tembotrione Chemical compound ClC1=C(COCC(F)(F)F)C(S(=O)(=O)C)=CC=C1C(=O)C1C(=O)CCCC1=O IUQAXCIUEPFPSF-UHFFFAOYSA-N 0.000 description 1
- FZXISNSWEXTPMF-UHFFFAOYSA-N terbutylazine Chemical compound CCNC1=NC(Cl)=NC(NC(C)(C)C)=N1 FZXISNSWEXTPMF-UHFFFAOYSA-N 0.000 description 1
- GLDAZAQRGCSFNP-UHFFFAOYSA-N thiencarbazone Chemical compound O=C1N(C)C(OC)=NN1C(=O)NS(=O)(=O)C1=C(C)SC=C1C(O)=O GLDAZAQRGCSFNP-UHFFFAOYSA-N 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- SRVJKTDHMYAMHA-WUXMJOGZSA-N thioacetazone Chemical group CC(=O)NC1=CC=C(\C=N\NC(N)=S)C=C1 SRVJKTDHMYAMHA-WUXMJOGZSA-N 0.000 description 1
- 229960003231 thioacetazone Drugs 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 235000010215 titanium dioxide Nutrition 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 229960002622 triacetin Drugs 0.000 description 1
- REEQLXCGVXDJSQ-UHFFFAOYSA-N trichlopyr Chemical compound OC(=O)COC1=NC(Cl)=C(Cl)C=C1Cl REEQLXCGVXDJSQ-UHFFFAOYSA-N 0.000 description 1
- ZMANZCXQSJIPKH-UHFFFAOYSA-O triethylammonium ion Chemical compound CC[NH+](CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-O 0.000 description 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
- ZSDSQXJSNMTJDA-UHFFFAOYSA-N trifluralin Chemical compound CCCN(CCC)C1=C([N+]([O-])=O)C=C(C(F)(F)F)C=C1[N+]([O-])=O ZSDSQXJSNMTJDA-UHFFFAOYSA-N 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 229940005605 valeric acid Drugs 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- NWONKYPBYAMBJT-UHFFFAOYSA-L zinc sulfate Chemical class [Zn+2].[O-]S([O-])(=O)=O NWONKYPBYAMBJT-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
- A01N25/30—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests characterised by the surfactants
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
- A01N47/36—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the group >N—CO—N< directly attached to at least one heterocyclic ring; Thio analogues thereof
-
- 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
- A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
- A01N43/66—1,3,5-Triazines, not hydrogenated and not substituted at the ring nitrogen atoms
- A01N43/68—1,3,5-Triazines, not hydrogenated and not substituted at the ring nitrogen atoms with two or three nitrogen atoms directly attached to ring carbon atoms
- A01N43/70—Diamino—1,3,5—triazines with only one oxygen, sulfur or halogen atom or only one cyano, thiocyano (—SCN), cyanato (—OCN) or azido (—N3) group directly attached to a ring carbon atom
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Zoology (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Environmental Sciences (AREA)
- Plant Pathology (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Toxicology (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US71351805P | 2005-09-01 | 2005-09-01 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PT1947935E true PT1947935E (pt) | 2012-04-13 |
Family
ID=37685760
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PT06813996T PT1947935E (pt) | 2005-09-01 | 2006-08-31 | Formulações líquidas de herbicida de sulfonilureia |
Country Status (28)
| Country | Link |
|---|---|
| US (2) | US20090131257A1 (enExample) |
| EP (1) | EP1947935B1 (enExample) |
| JP (1) | JP5123855B2 (enExample) |
| KR (1) | KR101395979B1 (enExample) |
| CN (1) | CN101252836B (enExample) |
| AR (1) | AR055410A1 (enExample) |
| AT (1) | ATE542422T1 (enExample) |
| AU (1) | AU2006284759B2 (enExample) |
| BR (1) | BRPI0617122B1 (enExample) |
| CA (1) | CA2619625C (enExample) |
| DK (1) | DK1947935T3 (enExample) |
| EA (1) | EA013546B1 (enExample) |
| ES (1) | ES2380232T3 (enExample) |
| GT (1) | GT200600400A (enExample) |
| IL (1) | IL189219A (enExample) |
| MA (1) | MA29911B1 (enExample) |
| MX (1) | MX2008002749A (enExample) |
| MY (1) | MY148613A (enExample) |
| NZ (1) | NZ565510A (enExample) |
| PL (1) | PL1947935T3 (enExample) |
| PT (1) | PT1947935E (enExample) |
| RS (1) | RS52248B (enExample) |
| SI (1) | SI1947935T1 (enExample) |
| TN (1) | TNSN08098A1 (enExample) |
| TW (1) | TWI395547B (enExample) |
| UA (1) | UA93879C2 (enExample) |
| WO (1) | WO2007027863A2 (enExample) |
| ZA (1) | ZA200802442B (enExample) |
Families Citing this family (37)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SI1858330T1 (sl) * | 2005-03-14 | 2017-07-31 | Ishihara Sangyo Kaisha, Ltd. | Herbicidna suspenzija |
| JP4899582B2 (ja) * | 2005-04-26 | 2012-03-21 | 住友化学株式会社 | 除草用組成物 |
| US8463711B2 (en) | 2007-02-27 | 2013-06-11 | Igt | Methods and architecture for cashless system security |
| TW200843642A (en) * | 2007-03-08 | 2008-11-16 | Du Pont | Liquid sulfonylurea herbicide formulations |
| JP5360349B2 (ja) * | 2007-03-20 | 2013-12-04 | 日産化学工業株式会社 | 安定化される水性懸濁状農薬組成物 |
| GB0714451D0 (en) * | 2007-07-24 | 2007-09-05 | Syngenta Participations Ag | Herbicidal compositions |
| US10806143B2 (en) | 2009-10-13 | 2020-10-20 | Fmc Corporation | Herbicidal composition in granular form |
| JP5947789B2 (ja) | 2010-04-26 | 2016-07-06 | ダウ アグロサイエンシィズ エルエルシー | 安定化された農業用オイル分散物 |
| JP5829044B2 (ja) * | 2010-05-06 | 2015-12-09 | 石原産業株式会社 | 除草組成物 |
| DK2597956T3 (da) * | 2010-07-27 | 2014-12-15 | Dow Agrosciences Llc | Synergistiske herbicidale sammensætninger indeholdende pyroxsulam og sulfosulfuron |
| CN102037987B (zh) * | 2011-01-26 | 2013-07-24 | 江苏省农用激素工程技术研究中心有限公司 | 棉田除草剂组合物 |
| CN102067865B (zh) * | 2011-01-26 | 2013-06-05 | 江苏省农用激素工程技术研究中心有限公司 | 麦田除草剂组合物 |
| KR20140117580A (ko) * | 2012-01-25 | 2014-10-07 | 다우 아그로사이언시즈 엘엘씨 | 내부 보조제를 함유하는 개선된 고형 제초제 조성물 |
| CN102960357B (zh) * | 2012-12-11 | 2016-04-27 | 江苏龙灯化学有限公司 | 一种含莠灭净、甲磺草胺和啶嘧磺隆的除草组合物及其用途 |
| US10412964B2 (en) | 2012-12-14 | 2019-09-17 | Dow Agrosciences Llc | Synergistic weed control from applications of aminopyralid and clopyralid |
| HUE042793T2 (hu) | 2012-12-14 | 2019-07-29 | Dow Agrosciences Llc | Szinergetikus gyomirtás aminopiralid és klopiralid alkalmazásával |
| TR201818762T4 (tr) | 2012-12-21 | 2019-01-21 | Dow Agrosciences Llc | Sıcaklıkta stabil klokuintoset-meksil sulu bileşimler. |
| CN103960234B (zh) * | 2013-01-29 | 2016-12-28 | 粟贵武 | 磺酰脲类除草剂的新型稳定剂 |
| CN103355337B (zh) * | 2013-07-31 | 2015-03-18 | 联保作物科技有限公司 | 一种麦田除草组合物及其制剂 |
| CN103651477A (zh) * | 2013-11-18 | 2014-03-26 | 河北威远生化农药有限公司 | 一种玉米田专用除草剂 |
| US12016335B2 (en) | 2013-11-25 | 2024-06-25 | Fmc Corporation | Stabilized low-concentration metsulfuron-methyl liquid composition |
| RS57003B1 (sr) | 2013-11-25 | 2018-05-31 | E I Du Pont De Nemours And Copany | Stabilizovana tečna kompozicija metsulfuron-metila niske koncentracije |
| CN104686544B (zh) * | 2013-12-05 | 2016-09-14 | 南京华洲药业有限公司 | 一种含啶嘧磺隆与酰嘧磺隆的混合除草剂 |
| CN104273153A (zh) * | 2014-09-26 | 2015-01-14 | 青岛康和食品有限公司 | 一种水稻田禾草敌类除草剂组合物 |
| CN105532700A (zh) * | 2014-11-01 | 2016-05-04 | 南京华洲药业有限公司 | 一种含啶嘧磺隆、苄嘧磺隆与稗草畏的混合除草剂 |
| CN104396986A (zh) * | 2014-11-20 | 2015-03-11 | 江苏省激素研究所股份有限公司 | 一种玉米田复配除草剂 |
| CN107427010B (zh) | 2014-12-22 | 2020-07-17 | 三井农业化学国际有限公司 | 液态含磺酰脲的除草性组合物 |
| CN105935056B (zh) * | 2015-03-02 | 2018-06-15 | 四川利尔作物科学有限公司 | 除草组合物及其应用 |
| CN105191967A (zh) * | 2015-09-30 | 2015-12-30 | 河南科技学院 | 一种含有氟胺磺隆和噁唑酰草胺的除草组合物及其应用 |
| GB2545726B (en) * | 2015-12-23 | 2020-06-17 | Rotam Agrochem Int Co Ltd | Herbicidal composition and method for controlling plant growth |
| PL3416486T3 (pl) | 2016-06-21 | 2019-11-29 | Battelle Uk Ltd | Ciekłe kompozycje chwastobójcze zawierające sulfonylomocznik i sól Li |
| CA3017030A1 (en) * | 2016-11-18 | 2018-05-24 | Huntsman Corporation Australia Pty Limited | Co-formulation comprising a plant growth regulator and an oil, and methods of preparing and using said co-formulation |
| WO2020172305A1 (en) * | 2019-02-19 | 2020-08-27 | Gowan Company, L.L.C. | Stable liquid compositions and methods of using the same |
| WO2020234175A1 (en) * | 2019-05-21 | 2020-11-26 | Syngenta Crop Protection Ag | Improved herbicidal oil dispersion compositions |
| AR121156A1 (es) | 2020-01-29 | 2022-04-20 | Fmc Agricultural Caribe Ind Ltd | Composiciones de sulfonilureas líquidas |
| EP3900535A1 (en) | 2020-04-24 | 2021-10-27 | Battelle UK Limited | Liquid sulfonylurea herbicide composition |
| CN121057505A (zh) * | 2023-04-20 | 2025-12-02 | 安道麦阿甘有限公司 | 非水性除草配制品 |
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| IN164880B (enExample) | 1986-01-30 | 1989-06-24 | Ishihara Sangyo Kaisha | |
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| DE102004025220A1 (de) * | 2004-05-22 | 2005-12-08 | Bayer Cropscience Gmbh | Ölsuspensionskonzentrat |
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| WO2005041654A2 (de) * | 2003-11-03 | 2005-05-12 | Bayer Cropscience Gmbh | Herbizid wirksames mittel |
| RU2258366C1 (ru) | 2004-01-12 | 2005-08-20 | Государственное учреждение "Научно-исследовательский технологический институт гербицидов и регуляторов роста растений с опытно-экспериментальным производством" (НИТИГ) | Гербицидный состав и способ повышения химической стабильности хлорсульфурона в гербицидном смачивающемся порошке |
| SI1858330T1 (sl) | 2005-03-14 | 2017-07-31 | Ishihara Sangyo Kaisha, Ltd. | Herbicidna suspenzija |
-
2005
- 2005-08-31 ZA ZA200802442A patent/ZA200802442B/xx unknown
-
2006
- 2006-08-09 TW TW095129139A patent/TWI395547B/zh not_active IP Right Cessation
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- 2006-08-31 WO PCT/US2006/033986 patent/WO2007027863A2/en not_active Ceased
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2013
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