UA73351C2 - Liquid formulation - Google Patents
Liquid formulation Download PDFInfo
- Publication number
- UA73351C2 UA73351C2 UA2002119419A UA2002119419A UA73351C2 UA 73351 C2 UA73351 C2 UA 73351C2 UA 2002119419 A UA2002119419 A UA 2002119419A UA 2002119419 A UA2002119419 A UA 2002119419A UA 73351 C2 UA73351 C2 UA 73351C2
- Authority
- UA
- Ukraine
- Prior art keywords
- group
- carbon atoms
- inhibitors
- active substances
- acid
- Prior art date
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- 239000012669 liquid formulation Substances 0.000 title abstract 2
- 239000013543 active substance Substances 0.000 claims abstract description 46
- 239000002253 acid Substances 0.000 claims abstract description 43
- 238000002360 preparation method Methods 0.000 claims abstract description 43
- 239000003112 inhibitor Substances 0.000 claims abstract description 34
- 150000007513 acids Chemical class 0.000 claims abstract description 28
- 125000004432 carbon atom Chemical group C* 0.000 claims description 95
- -1 carboxyethyl Chemical group 0.000 claims description 72
- 125000000217 alkyl group Chemical group 0.000 claims description 50
- 239000007788 liquid Substances 0.000 claims description 34
- 150000001875 compounds Chemical class 0.000 claims description 33
- 125000002947 alkylene group Chemical group 0.000 claims description 30
- 229940100389 Sulfonylurea Drugs 0.000 claims description 22
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 20
- ULUAUXLGCMPNKK-UHFFFAOYSA-N Sulfobutanedioic acid Chemical class OC(=O)CC(C(O)=O)S(O)(=O)=O ULUAUXLGCMPNKK-UHFFFAOYSA-N 0.000 claims description 15
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 15
- 239000003905 agrochemical Substances 0.000 claims description 12
- 239000004094 surface-active agent Substances 0.000 claims description 11
- 239000000839 emulsion Substances 0.000 claims description 10
- 239000003960 organic solvent Substances 0.000 claims description 10
- 150000001768 cations Chemical class 0.000 claims description 9
- 239000012141 concentrate Substances 0.000 claims description 9
- 239000000203 mixture Substances 0.000 claims description 9
- 229920000642 polymer Polymers 0.000 claims description 9
- 239000006185 dispersion Substances 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 7
- 239000000243 solution Substances 0.000 claims description 7
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid group Chemical group S(O)(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 4
- 229920006395 saturated elastomer Polymers 0.000 claims description 4
- 125000004434 sulfur atom Chemical group 0.000 claims description 4
- 108010000700 Acetolactate synthase Proteins 0.000 claims description 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical group OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 3
- 238000002156 mixing Methods 0.000 claims description 3
- 230000008635 plant growth Effects 0.000 claims description 3
- 229930195734 saturated hydrocarbon Natural products 0.000 claims description 3
- KWIUHFFTVRNATP-UHFFFAOYSA-O N,N,N-trimethylglycinium Chemical group C[N+](C)(C)CC(O)=O KWIUHFFTVRNATP-UHFFFAOYSA-O 0.000 claims description 2
- 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 claims description 2
- 238000010790 dilution Methods 0.000 claims description 2
- 239000012895 dilution Substances 0.000 claims description 2
- 125000005647 linker group Chemical group 0.000 claims description 2
- 125000004437 phosphorous atom Chemical group 0.000 claims description 2
- 229920000233 poly(alkylene oxides) Polymers 0.000 claims description 2
- 229930195735 unsaturated hydrocarbon Natural products 0.000 claims description 2
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 3
- 235000015107 ale Nutrition 0.000 claims 1
- 125000004962 sulfoxyl group Chemical group 0.000 claims 1
- 238000012876 topography Methods 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 35
- 150000003839 salts Chemical class 0.000 description 25
- 239000000729 antidote Substances 0.000 description 20
- 239000004009 herbicide Substances 0.000 description 18
- 125000001188 haloalkyl group Chemical group 0.000 description 16
- 150000002430 hydrocarbons Chemical group 0.000 description 15
- 239000000126 substance Substances 0.000 description 13
- 241000196324 Embryophyta Species 0.000 description 12
- 230000006378 damage Effects 0.000 description 12
- 150000002148 esters Chemical class 0.000 description 12
- ICJSJAJWTWPSBD-UHFFFAOYSA-N cloquintocet Chemical compound C1=CN=C2C(OCC(=O)O)=CC=C(Cl)C2=C1 ICJSJAJWTWPSBD-UHFFFAOYSA-N 0.000 description 11
- 150000001408 amides Chemical class 0.000 description 10
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 10
- 230000003993 interaction Effects 0.000 description 10
- 125000001424 substituent group Chemical group 0.000 description 10
- 125000003118 aryl group Chemical group 0.000 description 9
- 150000004702 methyl esters Chemical class 0.000 description 9
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 8
- 150000001735 carboxylic acids Chemical class 0.000 description 8
- 230000002363 herbicidal effect Effects 0.000 description 8
- 125000000623 heterocyclic group Chemical group 0.000 description 8
- 239000000463 material Substances 0.000 description 8
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 7
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 7
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- 241000209094 Oryza Species 0.000 description 7
- 235000007164 Oryza sativa Nutrition 0.000 description 7
- 125000003342 alkenyl group Chemical group 0.000 description 7
- 125000000304 alkynyl group Chemical group 0.000 description 7
- 229940075522 antidotes Drugs 0.000 description 7
- 125000001072 heteroaryl group Chemical group 0.000 description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 7
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 7
- 235000009566 rice Nutrition 0.000 description 7
- 159000000000 sodium salts Chemical class 0.000 description 7
- 229940124530 sulfonamide Drugs 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 6
- 150000001298 alcohols Chemical class 0.000 description 6
- 150000001412 amines Chemical class 0.000 description 6
- 125000003277 amino group Chemical group 0.000 description 6
- 125000004122 cyclic group Chemical group 0.000 description 6
- WCGGWVOVFQNRRS-UHFFFAOYSA-N dichloroacetamide Chemical compound NC(=O)C(Cl)Cl WCGGWVOVFQNRRS-UHFFFAOYSA-N 0.000 description 6
- 235000014113 dietary fatty acids Nutrition 0.000 description 6
- 229930195729 fatty acid Natural products 0.000 description 6
- 239000000194 fatty acid Substances 0.000 description 6
- 150000004665 fatty acids Chemical class 0.000 description 6
- 239000008187 granular material Substances 0.000 description 6
- 229910052751 metal Inorganic materials 0.000 description 6
- 239000002184 metal Substances 0.000 description 6
- 230000003647 oxidation Effects 0.000 description 6
- 238000007254 oxidation reaction Methods 0.000 description 6
- 239000000725 suspension Substances 0.000 description 6
- WVQBLGZPHOPPFO-UHFFFAOYSA-N 2-chloro-N-(2-ethyl-6-methylphenyl)-N-(1-methoxypropan-2-yl)acetamide Chemical compound CCC1=CC=CC(C)=C1N(C(C)COC)C(=O)CCl WVQBLGZPHOPPFO-UHFFFAOYSA-N 0.000 description 5
- 241000252067 Megalops atlanticus Species 0.000 description 5
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 5
- 239000000654 additive Substances 0.000 description 5
- 150000001340 alkali metals Chemical class 0.000 description 5
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 5
- 125000005843 halogen group Chemical group 0.000 description 5
- 125000005842 heteroatom Chemical group 0.000 description 5
- ITGSCCPVERXFGN-UHFFFAOYSA-N isoxadifen Chemical compound C1C(C(=O)O)=NOC1(C=1C=CC=CC=1)C1=CC=CC=C1 ITGSCCPVERXFGN-UHFFFAOYSA-N 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 239000003921 oil Substances 0.000 description 5
- 235000019260 propionic acid Nutrition 0.000 description 5
- 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 5
- 239000011734 sodium Substances 0.000 description 5
- 229910052708 sodium Inorganic materials 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 238000003860 storage Methods 0.000 description 5
- 239000012224 working solution Substances 0.000 description 5
- CAAMSDWKXXPUJR-UHFFFAOYSA-N 3,5-dihydro-4H-imidazol-4-one Chemical class O=C1CNC=N1 CAAMSDWKXXPUJR-UHFFFAOYSA-N 0.000 description 4
- 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 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 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 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 4
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 4
- 240000008042 Zea mays Species 0.000 description 4
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 4
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 4
- 125000001931 aliphatic group Chemical group 0.000 description 4
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 4
- 239000003513 alkali Substances 0.000 description 4
- 229910052783 alkali metal Inorganic materials 0.000 description 4
- 125000002877 alkyl aryl group Chemical group 0.000 description 4
- 230000001166 anti-perspirative effect Effects 0.000 description 4
- 239000003213 antiperspirant Substances 0.000 description 4
- 150000004945 aromatic hydrocarbons Chemical group 0.000 description 4
- 239000004202 carbamide Substances 0.000 description 4
- 235000005822 corn Nutrition 0.000 description 4
- 125000004093 cyano group Chemical group *C#N 0.000 description 4
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 4
- 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 description 4
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 4
- 239000003755 preservative agent Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium Chemical compound [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 description 4
- DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 4
- URAYPUMNDPQOKB-UHFFFAOYSA-N triacetin Chemical compound CC(=O)OCC(OC(C)=O)COC(C)=O URAYPUMNDPQOKB-UHFFFAOYSA-N 0.000 description 4
- ABOOPXYCKNFDNJ-UHFFFAOYSA-N 2-{4-[(6-chloroquinoxalin-2-yl)oxy]phenoxy}propanoic acid Chemical compound C1=CC(OC(C)C(O)=O)=CC=C1OC1=CN=C(C=C(Cl)C=C2)C2=N1 ABOOPXYCKNFDNJ-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- 239000003666 Amidosulfuron Substances 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 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 description 3
- PQKBPHSEKWERTG-UHFFFAOYSA-N Fenoxaprop ethyl Chemical group C1=CC(OC(C)C(=O)OCC)=CC=C1OC1=NC2=CC=C(Cl)C=C2O1 PQKBPHSEKWERTG-UHFFFAOYSA-N 0.000 description 3
- 239000005560 Foramsulfuron Substances 0.000 description 3
- 239000005584 Metsulfuron-methyl Substances 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 239000005586 Nicosulfuron Substances 0.000 description 3
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 3
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 3
- 239000005616 Rimsulfuron Substances 0.000 description 3
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000001089 [(2R)-oxolan-2-yl]methanol Substances 0.000 description 3
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 3
- 125000003282 alkyl amino group Chemical group 0.000 description 3
- 125000004448 alkyl carbonyl group Chemical group 0.000 description 3
- 150000005215 alkyl ethers Chemical class 0.000 description 3
- 125000004414 alkyl thio group Chemical group 0.000 description 3
- 125000004429 atom Chemical group 0.000 description 3
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 3
- 229940088623 biologically active substance Drugs 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 3
- 125000000753 cycloalkyl group Chemical group 0.000 description 3
- 125000004663 dialkyl amino group Chemical group 0.000 description 3
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 3
- 239000000975 dye Substances 0.000 description 3
- 125000004494 ethyl ester group Chemical group 0.000 description 3
- 230000002349 favourable effect Effects 0.000 description 3
- 239000003337 fertilizer Substances 0.000 description 3
- PXDNXJSDGQBLKS-UHFFFAOYSA-N foramsulfuron Chemical compound COC1=CC(OC)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=C(NC=O)C=2)C(=O)N(C)C)=N1 PXDNXJSDGQBLKS-UHFFFAOYSA-N 0.000 description 3
- 239000003205 fragrance Substances 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 150000002367 halogens Chemical class 0.000 description 3
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 3
- 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 description 3
- ZTYVMAQSHCZXLF-UHFFFAOYSA-N methyl 2-[[4,6-bis(difluoromethoxy)pyrimidin-2-yl]carbamoylsulfamoyl]benzoate Chemical group COC(=O)C1=CC=CC=C1S(=O)(=O)NC(=O)NC1=NC(OC(F)F)=CC(OC(F)F)=N1 ZTYVMAQSHCZXLF-UHFFFAOYSA-N 0.000 description 3
- VWGAYSCWLXQJBQ-UHFFFAOYSA-N methyl 4-iodo-2-[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)carbamoylsulfamoyl]benzoate Chemical group COC(=O)C1=CC=C(I)C=C1S(=O)(=O)NC(=O)NC1=NC(C)=NC(OC)=N1 VWGAYSCWLXQJBQ-UHFFFAOYSA-N 0.000 description 3
- 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 3
- 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 description 3
- 235000001968 nicotinic acid Nutrition 0.000 description 3
- 239000011664 nicotinic acid Substances 0.000 description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 description 3
- 235000019198 oils Nutrition 0.000 description 3
- 125000004043 oxo group Chemical group O=* 0.000 description 3
- 239000000575 pesticide Substances 0.000 description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 3
- 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 description 3
- 238000007142 ring opening reaction Methods 0.000 description 3
- 239000002689 soil Substances 0.000 description 3
- 125000000547 substituted alkyl group Chemical group 0.000 description 3
- YROXIXLRRCOBKF-UHFFFAOYSA-N sulfonylurea Chemical class OC(=N)N=S(=O)=O YROXIXLRRCOBKF-UHFFFAOYSA-N 0.000 description 3
- BSYVTEYKTMYBMK-UHFFFAOYSA-N tetrahydrofurfuryl alcohol Chemical compound OCC1CCCO1 BSYVTEYKTMYBMK-UHFFFAOYSA-N 0.000 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 description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 3
- HKELWJONQIFBPO-UHFFFAOYSA-N 1-(2,4-dichlorophenyl)-5-(trichloromethyl)-1,2,4-triazole-3-carboxylic acid Chemical compound N1=C(C(=O)O)N=C(C(Cl)(Cl)Cl)N1C1=CC=C(Cl)C=C1Cl HKELWJONQIFBPO-UHFFFAOYSA-N 0.000 description 2
- AJFKCJRMHHBFNS-UHFFFAOYSA-N 1-(2,4-dichlorophenyl)-5-phenylpyrazole-3-carboxylic acid Chemical compound C=1C=C(Cl)C=C(Cl)C=1N1N=C(C(=O)O)C=C1C1=CC=CC=C1 AJFKCJRMHHBFNS-UHFFFAOYSA-N 0.000 description 2
- MQPLQJSDTDAHBC-UHFFFAOYSA-N 1-(2,4-dichlorophenyl)-5-propan-2-ylpyrazole-3-carboxylic acid Chemical compound CC(C)C1=CC(C(O)=O)=NN1C1=CC=C(Cl)C=C1Cl MQPLQJSDTDAHBC-UHFFFAOYSA-N 0.000 description 2
- 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 description 2
- BBMCTIGTTCKYKF-UHFFFAOYSA-N 1-heptanol Chemical compound CCCCCCCO BBMCTIGTTCKYKF-UHFFFAOYSA-N 0.000 description 2
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 2
- QPUYECUOLPXSFR-UHFFFAOYSA-N 1-methylnaphthalene Chemical compound C1=CC=C2C(C)=CC=CC2=C1 QPUYECUOLPXSFR-UHFFFAOYSA-N 0.000 description 2
- OVSKIKFHRZPJSS-UHFFFAOYSA-N 2,4-D Chemical compound OC(=O)COC1=CC=C(Cl)C=C1Cl OVSKIKFHRZPJSS-UHFFFAOYSA-N 0.000 description 2
- WNTGYJSOUMFZEP-UHFFFAOYSA-N 2-(4-chloro-2-methylphenoxy)propanoic acid Chemical compound OC(=O)C(C)OC1=CC=C(Cl)C=C1C WNTGYJSOUMFZEP-UHFFFAOYSA-N 0.000 description 2
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- HRRDCWDFRIJIQZ-UHFFFAOYSA-N naphthalene-1,8-dicarboxylic acid Chemical compound C1=CC(C(O)=O)=C2C(C(=O)O)=CC=CC2=C1 HRRDCWDFRIJIQZ-UHFFFAOYSA-N 0.000 description 1
- UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene-acid Natural products C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 1
- 150000002790 naphthalenes Chemical class 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 239000012454 non-polar solvent Substances 0.000 description 1
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 1
- FATBGEAMYMYZAF-KTKRTIGZSA-N oleamide Chemical compound CCCCCCCC\C=C/CCCCCCCC(N)=O FATBGEAMYMYZAF-KTKRTIGZSA-N 0.000 description 1
- 125000001117 oleyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])/C([H])=C([H])\C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229940113162 oleylamide Drugs 0.000 description 1
- 150000002892 organic cations Chemical class 0.000 description 1
- IOXAXYHXMLCCJJ-UHFFFAOYSA-N oxetan-3-yl 2-[(4,6-dimethylpyrimidin-2-yl)carbamoylsulfamoyl]benzoate Chemical compound CC1=CC(C)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)C(=O)OC2COC2)=N1 IOXAXYHXMLCCJJ-UHFFFAOYSA-N 0.000 description 1
- 150000002923 oximes Chemical class 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- LCPDWSOZIOUXRV-UHFFFAOYSA-N phenoxyacetic acid Chemical class OC(=O)COC1=CC=CC=C1 LCPDWSOZIOUXRV-UHFFFAOYSA-N 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical compound [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 description 1
- 150000004714 phosphonium salts Chemical class 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- HFGGXBQZQRVOKM-UHFFFAOYSA-N piperidine-1-carbothioic s-acid Chemical compound SC(=O)N1CCCCC1 HFGGXBQZQRVOKM-UHFFFAOYSA-N 0.000 description 1
- 239000002574 poison Substances 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 229920001444 polymaleic acid Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- FROBCXTULYFHEJ-OAHLLOKOSA-N propaquizafop Chemical compound C1=CC(O[C@H](C)C(=O)OCCON=C(C)C)=CC=C1OC1=CN=C(C=C(Cl)C=C2)C2=N1 FROBCXTULYFHEJ-OAHLLOKOSA-N 0.000 description 1
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-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
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 239000003223 protective agent Substances 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 description 1
- 125000005554 pyridyloxy group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- JKPSVOHVUGMYGH-UHFFFAOYSA-M sodium;(4,6-dimethoxypyrimidin-2-yl)-[[3-methoxycarbonyl-6-(trifluoromethyl)pyridin-2-yl]sulfonylcarbamoyl]azanide Chemical compound [Na+].COC(=O)C1=CC=C(C(F)(F)F)N=C1S(=O)(=O)NC(=O)[N-]C1=NC(OC)=CC(OC)=N1 JKPSVOHVUGMYGH-UHFFFAOYSA-M 0.000 description 1
- RSUPHLZUJCEDNP-UHFFFAOYSA-M sodium;4-hydroxy-1-octan-3-yloxy-1,4-dioxobutane-2-sulfonate Chemical compound [Na+].CCCCCC(CC)OC(=O)C(S(O)(=O)=O)CC([O-])=O RSUPHLZUJCEDNP-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000001694 spray drying Methods 0.000 description 1
- 238000003892 spreading Methods 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- PQTBTIFWAXVEPB-UHFFFAOYSA-N sulcotrione Chemical compound ClC1=CC(S(=O)(=O)C)=CC=C1C(=O)C1C(=O)CCCC1=O PQTBTIFWAXVEPB-UHFFFAOYSA-N 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 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
- 125000000565 sulfonamide group Chemical group 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 229920001897 terpolymer Polymers 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- ZUHZGEOKBKGPSW-UHFFFAOYSA-N tetraglyme Chemical compound COCCOCCOCCOCCOC ZUHZGEOKBKGPSW-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 150000003626 triacylglycerols Chemical class 0.000 description 1
- 239000001069 triethyl citrate Substances 0.000 description 1
- VMYFZRTXGLUXMZ-UHFFFAOYSA-N triethyl citrate Natural products CCOC(=O)C(O)(C(=O)OCC)C(=O)OCC VMYFZRTXGLUXMZ-UHFFFAOYSA-N 0.000 description 1
- 235000013769 triethyl citrate Nutrition 0.000 description 1
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 1
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 150000003738 xylenes Chemical class 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
- 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
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- General Health & Medical Sciences (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Medicinal Preparation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10020671A DE10020671A1 (de) | 2000-04-27 | 2000-04-27 | Flüssige Formulierungen |
| PCT/EP2001/003879 WO2001082693A2 (de) | 2000-04-27 | 2001-04-05 | Flüssige formulierungen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| UA73351C2 true UA73351C2 (en) | 2005-07-15 |
Family
ID=7640122
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| UA2002119419A UA73351C2 (en) | 2000-04-27 | 2001-05-04 | Liquid formulation |
Country Status (28)
| Country | Link |
|---|---|
| US (1) | US20020016263A1 (pt) |
| EP (1) | EP1278416B1 (pt) |
| JP (1) | JP2003531838A (pt) |
| CN (1) | CN1209023C (pt) |
| AR (1) | AR028369A1 (pt) |
| AT (1) | ATE263487T1 (pt) |
| AU (2) | AU2001263839B2 (pt) |
| BR (1) | BR0110406A (pt) |
| CA (1) | CA2407269C (pt) |
| CL (1) | CL2004001255A1 (pt) |
| CZ (1) | CZ299413B6 (pt) |
| DE (2) | DE10020671A1 (pt) |
| DK (1) | DK1278416T3 (pt) |
| ES (1) | ES2219527T3 (pt) |
| HR (1) | HRP20020844B1 (pt) |
| HU (1) | HU230145B1 (pt) |
| MX (1) | MXPA02010648A (pt) |
| MY (1) | MY127749A (pt) |
| PL (1) | PL203957B1 (pt) |
| PT (1) | PT1278416E (pt) |
| RS (1) | RS50504B (pt) |
| RU (1) | RU2324350C9 (pt) |
| SK (1) | SK287077B6 (pt) |
| TR (1) | TR200401645T4 (pt) |
| TW (1) | TWI256288B (pt) |
| UA (1) | UA73351C2 (pt) |
| WO (1) | WO2001082693A2 (pt) |
| ZA (1) | ZA200208656B (pt) |
Families Citing this family (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE10108472A1 (de) * | 2001-02-22 | 2002-09-05 | Aventis Cropscience Gmbh | Agrochemische Formulierungen |
| EA012031B1 (ru) * | 2002-12-13 | 2009-06-30 | Байер Кропсайенс Аг | Гербицидный масляный суспензионный концентрат, способ его получения, применения и способ борьбы с сорными растениями |
| DE102004025220A1 (de) * | 2004-05-22 | 2005-12-08 | Bayer Cropscience Gmbh | Ölsuspensionskonzentrat |
| DE10334300A1 (de) * | 2003-07-28 | 2005-03-03 | Bayer Cropscience Gmbh | Ölsuspensionskonzentrat |
| DE10334301A1 (de) * | 2003-07-28 | 2005-03-03 | Bayer Cropscience Gmbh | Flüssige Formulierung |
| EP1681932B1 (de) * | 2003-11-03 | 2008-03-19 | Bayer CropScience AG | Herbizid wirksames mittel |
| US20050244357A1 (en) * | 2004-02-26 | 2005-11-03 | Eward Sieverding | Oil-containing emulsifiable formulations containing active agents |
| DE102004011007A1 (de) | 2004-03-06 | 2005-09-22 | Bayer Cropscience Ag | Suspensionskonzentrate auf Ölbasis |
| JP2008542313A (ja) * | 2005-06-04 | 2008-11-27 | バイエル・クロツプサイエンス・アクチエンゲゼルシヤフト | 油性懸濁製剤 |
| ZA200802442B (en) * | 2005-09-01 | 2010-02-24 | Du Pont | Liquid sulfonylurea herbicide formulations |
| DE102005056744A1 (de) * | 2005-11-29 | 2007-05-31 | Bayer Cropscience Gmbh | Flüssige Formulierungen enthaltend Dialkylsulfosuccinate und Inhibitoren der Hydroxyphenylpyruvat-Dioxygenase |
| TW200843642A (en) * | 2007-03-08 | 2008-11-16 | Du Pont | Liquid sulfonylurea herbicide formulations |
| WO2011076731A1 (de) | 2009-12-23 | 2011-06-30 | Bayer Cropscience Ag | Flüssige formulierung von 2-iodo-n-[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)carbamoyl] benzolsulfonamid |
| ES2891316T3 (es) * | 2010-10-15 | 2022-01-27 | Bayer Cropscience Ag | Uso de herbicidas inhibidores de ALS para el control de vegetación indeseada en plantas Beta vulgaris tolerantes a herbicidas inhibidores de ALS |
| EP2723175B1 (en) * | 2011-06-22 | 2017-05-17 | Dow AgroSciences LLC | Herbicide granules with built-in adjuvant |
| RU2606771C2 (ru) * | 2011-06-22 | 2017-01-10 | Доу Агросаенсиз Ллк | Гербицидные эмульгируемые концентраты со вспомогательным веществом |
| JP6028017B2 (ja) * | 2012-04-13 | 2016-11-16 | ライオン株式会社 | アルコキシル化触媒、前記触媒の製造方法、及び前記触媒を用いた脂肪酸アルキルエステルアルコキシレートの製造方法 |
| SI2854543T1 (sl) | 2012-05-25 | 2016-12-30 | Bayer Cropscience Ag | Kemijska stabilizacija jodosulfuron-metil-natrijeve soli z uporabo hidroksistearatov |
| DK3073823T3 (en) | 2013-11-25 | 2018-04-09 | Du Pont | STABILIZED LOW CONCENTRATION OF LOW CONCENTRATION OF METSULFURON METHYL |
| US12016335B2 (en) | 2013-11-25 | 2024-06-25 | Fmc Corporation | Stabilized low-concentration metsulfuron-methyl liquid composition |
| UA119191C2 (uk) | 2014-12-15 | 2019-05-10 | Байєр Кропсайєнс Акцієнгезелльшафт | Кристалічні форми мононатрієвої солі форамсульфурону |
| EP3331359B1 (en) * | 2015-08-04 | 2021-03-17 | Rhodia Operations | Agricultural adjuvant compositions and methods for using such compositions |
| RU2694633C1 (ru) * | 2018-11-26 | 2019-07-16 | ООО "Агро Эксперт Груп" | Жидкая гербицидная композиция на основе трифлусульфурон-метила |
| US20220132854A1 (en) | 2019-02-19 | 2022-05-05 | Gowan Company, L.L.C. | Stable liquid compositions and methods of using the same |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SU1269296A1 (ru) * | 1984-07-02 | 1996-03-10 | Р.Б. Валитов | Гербицидный состав |
| DK0514768T3 (pt) * | 1991-05-18 | 1997-02-17 | Hoechst Schering Agrevo Gmbh | |
| DK0554015T3 (da) * | 1992-01-28 | 1995-06-06 | Ishihara Sangyo Kaisha | Kemisk stabiliseret herbicidisk olie-baseret suspension |
| RU2040179C1 (ru) * | 1992-09-04 | 1995-07-25 | Латвийская фирма "КАРЕ" | Синергетический гербицидный состав и способ борьбы с нежелательной растительностью |
| RU2040180C1 (ru) * | 1992-09-04 | 1995-07-25 | Латвийская фирма "КАРЕ" | Гербицидный синергитический состав |
| ES2123033T3 (es) * | 1992-11-18 | 1999-01-01 | Ishihara Sangyo Kaisha | Metodo para aumentar la actividad herbicida, composicion herbicida con actividad aumentada y composicion para aumentar la actividad. |
| JPH06239711A (ja) * | 1992-12-25 | 1994-08-30 | Ishihara Sangyo Kaisha Ltd | 除草組成物 |
| JPH06321713A (ja) * | 1993-05-07 | 1994-11-22 | Mitsubishi Petrochem Co Ltd | 水田用懸濁状除草剤組成物 |
| DE10334301A1 (de) * | 2003-07-28 | 2005-03-03 | Bayer Cropscience Gmbh | Flüssige Formulierung |
-
2000
- 2000-04-27 DE DE10020671A patent/DE10020671A1/de not_active Ceased
-
2001
- 2001-04-05 DK DK01938088T patent/DK1278416T3/da active
- 2001-04-05 ES ES01938088T patent/ES2219527T3/es not_active Expired - Lifetime
- 2001-04-05 AU AU2001263839A patent/AU2001263839B2/en not_active Expired
- 2001-04-05 EP EP01938088A patent/EP1278416B1/de not_active Expired - Lifetime
- 2001-04-05 WO PCT/EP2001/003879 patent/WO2001082693A2/de active IP Right Grant
- 2001-04-05 CA CA002407269A patent/CA2407269C/en not_active Expired - Lifetime
- 2001-04-05 BR BR0110406-3A patent/BR0110406A/pt not_active Application Discontinuation
- 2001-04-05 MX MXPA02010648A patent/MXPA02010648A/es active IP Right Grant
- 2001-04-05 SK SK1531-2002A patent/SK287077B6/sk not_active IP Right Cessation
- 2001-04-05 RS YUP-782/02A patent/RS50504B/sr unknown
- 2001-04-05 CN CNB018097758A patent/CN1209023C/zh not_active Expired - Lifetime
- 2001-04-05 DE DE50101916T patent/DE50101916D1/de not_active Expired - Fee Related
- 2001-04-05 PT PT01938088T patent/PT1278416E/pt unknown
- 2001-04-05 PL PL365795A patent/PL203957B1/pl unknown
- 2001-04-05 TR TR2004/01645T patent/TR200401645T4/xx unknown
- 2001-04-05 AU AU6383901A patent/AU6383901A/xx active Pending
- 2001-04-05 AT AT01938088T patent/ATE263487T1/de active
- 2001-04-05 CZ CZ20023572A patent/CZ299413B6/cs not_active IP Right Cessation
- 2001-04-05 JP JP2001579586A patent/JP2003531838A/ja not_active Ceased
- 2001-04-05 HU HU0300653A patent/HU230145B1/hu unknown
- 2001-04-05 RU RU2002132187/15A patent/RU2324350C9/ru active
- 2001-04-25 AR ARP010101942A patent/AR028369A1/es active IP Right Grant
- 2001-04-25 TW TW090109935A patent/TWI256288B/zh not_active IP Right Cessation
- 2001-04-25 US US09/841,820 patent/US20020016263A1/en not_active Abandoned
- 2001-04-26 MY MYPI20011958A patent/MY127749A/en unknown
- 2001-05-04 UA UA2002119419A patent/UA73351C2/uk unknown
-
2002
- 2002-10-24 HR HR20020844A patent/HRP20020844B1/xx not_active IP Right Cessation
- 2002-10-25 ZA ZA200208656A patent/ZA200208656B/xx unknown
-
2004
- 2004-05-24 CL CL200401255A patent/CL2004001255A1/es unknown
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