JPS6236029B2 - - Google Patents
Info
- Publication number
- JPS6236029B2 JPS6236029B2 JP52039062A JP3906277A JPS6236029B2 JP S6236029 B2 JPS6236029 B2 JP S6236029B2 JP 52039062 A JP52039062 A JP 52039062A JP 3906277 A JP3906277 A JP 3906277A JP S6236029 B2 JPS6236029 B2 JP S6236029B2
- Authority
- JP
- Japan
- Prior art keywords
- hydrogen
- carbon atoms
- methyl
- chlorine
- compound
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 150000001875 compounds Chemical class 0.000 claims description 144
- 239000001257 hydrogen Substances 0.000 claims description 110
- 229910052739 hydrogen Inorganic materials 0.000 claims description 110
- 125000004432 carbon atom Chemical group C* 0.000 claims description 87
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 82
- 239000000460 chlorine Substances 0.000 claims description 82
- 229910052801 chlorine Inorganic materials 0.000 claims description 82
- 150000002431 hydrogen Chemical class 0.000 claims description 78
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 69
- 239000011737 fluorine Substances 0.000 claims description 69
- 229910052731 fluorine Inorganic materials 0.000 claims description 69
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 68
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 54
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 54
- 229910052794 bromium Inorganic materials 0.000 claims description 54
- 125000003545 alkoxy group Chemical group 0.000 claims description 51
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 38
- -1 4-methoxy-6-methylpyrimidin-2-yl Chemical group 0.000 claims description 37
- 125000000217 alkyl group Chemical group 0.000 claims description 35
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 32
- 239000003795 chemical substances by application Substances 0.000 claims description 32
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 29
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 18
- 241000209140 Triticum Species 0.000 claims description 17
- 235000021307 Triticum Nutrition 0.000 claims description 17
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 17
- UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 claims description 16
- 150000003839 salts Chemical class 0.000 claims description 16
- 235000011684 Sorghum saccharatum Nutrition 0.000 claims description 10
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 10
- 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 10
- 229910052717 sulfur Inorganic materials 0.000 claims description 10
- 239000011593 sulfur Substances 0.000 claims description 10
- 239000004480 active ingredient Substances 0.000 claims description 9
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 8
- 240000006394 Sorghum bicolor Species 0.000 claims description 7
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 7
- 229910052760 oxygen Inorganic materials 0.000 claims description 7
- 239000001301 oxygen Substances 0.000 claims description 7
- 125000004306 triazinyl group Chemical group 0.000 claims description 7
- PUEXGEZHERTEAV-UHFFFAOYSA-N 1-(benzenesulfonyl)-3-(4,6-dimethylpyrimidin-2-yl)urea Chemical compound CC1=CC(C)=NC(NC(=O)NS(=O)(=O)C=2C=CC=CC=2)=N1 PUEXGEZHERTEAV-UHFFFAOYSA-N 0.000 claims description 6
- 230000001965 increasing effect Effects 0.000 claims description 6
- XHIBLMGCOLIHDE-UHFFFAOYSA-N 1-(2,5-dichlorophenyl)sulfonyl-3-(4,6-dimethoxypyrimidin-2-yl)urea Chemical compound COC1=CC(OC)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=C(Cl)C=2)Cl)=N1 XHIBLMGCOLIHDE-UHFFFAOYSA-N 0.000 claims description 5
- 240000000111 Saccharum officinarum Species 0.000 claims description 5
- 235000007201 Saccharum officinarum Nutrition 0.000 claims description 5
- 230000008635 plant growth Effects 0.000 claims description 5
- 235000000346 sugar Nutrition 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 230000002401 inhibitory effect Effects 0.000 claims description 4
- SLMTVWUDKVXNRS-UHFFFAOYSA-N 1-(2-chloro-5-methoxyphenyl)sulfonyl-3-(4-methoxy-6-methyl-1,3,5-triazin-2-yl)urea Chemical compound COC1=CC=C(Cl)C(S(=O)(=O)NC(=O)NC=2N=C(OC)N=C(C)N=2)=C1 SLMTVWUDKVXNRS-UHFFFAOYSA-N 0.000 claims description 3
- FVODUZFOZVJEBM-UHFFFAOYSA-N 1-(2-chloro-5-methoxyphenyl)sulfonyl-3-(4-methoxy-6-methylpyrimidin-2-yl)urea Chemical compound COC1=CC=C(Cl)C(S(=O)(=O)NC(=O)NC=2N=C(OC)C=C(C)N=2)=C1 FVODUZFOZVJEBM-UHFFFAOYSA-N 0.000 claims description 3
- IBDCEWGNSYXESG-UHFFFAOYSA-N 1-(4,6-dimethylpyrimidin-2-yl)-3-thiophen-2-ylsulfonylurea Chemical compound CC1=CC(C)=NC(NC(=O)NS(=O)(=O)C=2SC=CC=2)=N1 IBDCEWGNSYXESG-UHFFFAOYSA-N 0.000 claims description 3
- NMJNNILJNXDRKY-UHFFFAOYSA-N 1-(benzenesulfonyl)-3-(4,6-dimethyl-1,3,5-triazin-2-yl)urea Chemical compound CC1=NC(C)=NC(NC(=O)NS(=O)(=O)C=2C=CC=CC=2)=N1 NMJNNILJNXDRKY-UHFFFAOYSA-N 0.000 claims description 3
- 239000000575 pesticide Substances 0.000 claims description 3
- 239000005648 plant growth regulator Substances 0.000 claims description 3
- CSLLNEGBOBCILO-UHFFFAOYSA-N 1-(4-methoxy-6-methylpyrimidin-2-yl)-3-(2-methylphenyl)sulfonylurea Chemical compound COC1=CC(C)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)C)=N1 CSLLNEGBOBCILO-UHFFFAOYSA-N 0.000 claims description 2
- 239000003607 modifier Substances 0.000 claims 5
- 125000004317 1,3,5-triazin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=N1 0.000 claims 4
- JHUGAQBJCJJUFK-UHFFFAOYSA-N 1-(benzenesulfonyl)-3-(4-methoxy-6-methyl-1,3,5-triazin-2-yl)urea Chemical compound COC1=NC(C)=NC(NC(=O)NS(=O)(=O)C=2C=CC=CC=2)=N1 JHUGAQBJCJJUFK-UHFFFAOYSA-N 0.000 claims 2
- JCCBZCMSYUSCFM-UHFFFAOYSA-N 2-chlorobenzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1Cl JCCBZCMSYUSCFM-UHFFFAOYSA-N 0.000 claims 2
- 239000003905 agrochemical Substances 0.000 claims 2
- KQZACOKPRVJOMN-UHFFFAOYSA-N 1-(benzenesulfonyl)-3-(4,6-dimethoxypyrimidin-2-yl)urea Chemical compound COC1=CC(OC)=NC(NC(=O)NS(=O)(=O)C=2C=CC=CC=2)=N1 KQZACOKPRVJOMN-UHFFFAOYSA-N 0.000 claims 1
- QJARBNAXWFCCKX-UHFFFAOYSA-N 2,3-dichlorobenzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC(Cl)=C1Cl QJARBNAXWFCCKX-UHFFFAOYSA-N 0.000 claims 1
- MMHMYFWOECSGDR-UHFFFAOYSA-N 2,5-dimethoxybenzenesulfonamide Chemical compound COC1=CC=C(OC)C(S(N)(=O)=O)=C1 MMHMYFWOECSGDR-UHFFFAOYSA-N 0.000 claims 1
- IARIOWWBALBFKZ-UHFFFAOYSA-N 2-chloro-5-methoxybenzenesulfonamide Chemical compound COC1=CC=C(Cl)C(S(N)(=O)=O)=C1 IARIOWWBALBFKZ-UHFFFAOYSA-N 0.000 claims 1
- YCMLQMDWSXFTIF-UHFFFAOYSA-N 2-methylbenzenesulfonimidic acid Chemical compound CC1=CC=CC=C1S(N)(=O)=O YCMLQMDWSXFTIF-UHFFFAOYSA-N 0.000 claims 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims 1
- 239000002373 plant growth inhibitor Substances 0.000 claims 1
- 241000196324 Embryophyta Species 0.000 description 40
- 238000002844 melting Methods 0.000 description 38
- 230000008018 melting Effects 0.000 description 38
- 239000000203 mixture Substances 0.000 description 38
- 239000002245 particle Substances 0.000 description 35
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 33
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
- 239000000047 product Substances 0.000 description 24
- 238000000034 method Methods 0.000 description 22
- 239000002904 solvent Substances 0.000 description 22
- 239000000463 material Substances 0.000 description 21
- 239000007787 solid Substances 0.000 description 21
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 18
- 239000000243 solution Substances 0.000 description 18
- 238000003756 stirring Methods 0.000 description 18
- 230000000694 effects Effects 0.000 description 16
- 239000004615 ingredient Substances 0.000 description 16
- 238000012360 testing method Methods 0.000 description 16
- 240000007594 Oryza sativa Species 0.000 description 15
- 235000007164 Oryza sativa Nutrition 0.000 description 15
- 239000000725 suspension Substances 0.000 description 15
- 230000012010 growth Effects 0.000 description 14
- 235000009566 rice Nutrition 0.000 description 14
- 239000007921 spray Substances 0.000 description 14
- 239000004563 wettable powder Substances 0.000 description 14
- 239000008187 granular material Substances 0.000 description 11
- 241000209149 Zea Species 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 10
- 239000004009 herbicide Substances 0.000 description 10
- 239000002689 soil Substances 0.000 description 10
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 9
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 9
- 235000005822 corn Nutrition 0.000 description 9
- 238000001914 filtration Methods 0.000 description 9
- 238000009472 formulation Methods 0.000 description 9
- 239000008188 pellet Substances 0.000 description 9
- 235000010469 Glycine max Nutrition 0.000 description 8
- 244000068988 Glycine max Species 0.000 description 8
- 244000299507 Gossypium hirsutum Species 0.000 description 8
- 230000004044 response Effects 0.000 description 8
- 238000005507 spraying Methods 0.000 description 8
- BUXTXUBQAKIQKS-UHFFFAOYSA-N sulfuryl diisocyanate Chemical class O=C=NS(=O)(=O)N=C=O BUXTXUBQAKIQKS-UHFFFAOYSA-N 0.000 description 8
- 229920000742 Cotton Polymers 0.000 description 7
- 150000001768 cations Chemical class 0.000 description 7
- YDEXUEFDPVHGHE-GGMCWBHBSA-L disodium;(2r)-3-(2-hydroxy-3-methoxyphenyl)-2-[2-methoxy-4-(3-sulfonatopropyl)phenoxy]propane-1-sulfonate Chemical compound [Na+].[Na+].COC1=CC=CC(C[C@H](CS([O-])(=O)=O)OC=2C(=CC(CCCS([O-])(=O)=O)=CC=2)OC)=C1O YDEXUEFDPVHGHE-GGMCWBHBSA-L 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- 244000075850 Avena orientalis Species 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 238000010521 absorption reaction Methods 0.000 description 6
- 238000007792 addition Methods 0.000 description 6
- 229960000892 attapulgite Drugs 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 231100001184 nonphytotoxic Toxicity 0.000 description 6
- 229910052625 palygorskite Inorganic materials 0.000 description 6
- 239000004576 sand Substances 0.000 description 6
- 239000002562 thickening agent Substances 0.000 description 6
- 239000002253 acid Substances 0.000 description 5
- 239000003085 diluting agent Substances 0.000 description 5
- 230000035784 germination Effects 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 238000002156 mixing Methods 0.000 description 5
- 239000012265 solid product Substances 0.000 description 5
- 241000894007 species Species 0.000 description 5
- 229940124530 sulfonamide Drugs 0.000 description 5
- 150000003456 sulfonamides Chemical class 0.000 description 5
- 239000004094 surface-active agent Substances 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- ZSVRWVNKIANBEK-UHFFFAOYSA-N 1-(2-chlorophenyl)sulfonyl-3-(4-methoxy-6-methylpyrimidin-2-yl)urea Chemical compound COC1=CC(C)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)Cl)=N1 ZSVRWVNKIANBEK-UHFFFAOYSA-N 0.000 description 4
- RSIQKLAMUSIUQA-UHFFFAOYSA-N 1-(benzenesulfonyl)-3-(4,6-dimethoxy-1,3,5-triazin-2-yl)urea Chemical compound COC1=NC(OC)=NC(NC(=O)NS(=O)(=O)C=2C=CC=CC=2)=N1 RSIQKLAMUSIUQA-UHFFFAOYSA-N 0.000 description 4
- 244000025254 Cannabis sativa Species 0.000 description 4
- 244000075634 Cyperus rotundus Species 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
- 241000209504 Poaceae Species 0.000 description 4
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 4
- 230000006378 damage Effects 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- 230000008020 evaporation Effects 0.000 description 4
- 239000012948 isocyanate Substances 0.000 description 4
- 150000002513 isocyanates Chemical class 0.000 description 4
- 229920000609 methyl cellulose Polymers 0.000 description 4
- 239000001923 methylcellulose Substances 0.000 description 4
- 235000010981 methylcellulose Nutrition 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 239000001488 sodium phosphate Substances 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- MKRAPJFQEAATPC-UHFFFAOYSA-N 1-(2-chlorophenyl)sulfonyl-3-(4,6-dimethoxy-1,3,5-triazin-2-yl)urea Chemical compound COC1=NC(OC)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)Cl)=N1 MKRAPJFQEAATPC-UHFFFAOYSA-N 0.000 description 3
- VFWCMGCRMGJXDK-UHFFFAOYSA-N 1-chlorobutane Chemical compound CCCCCl VFWCMGCRMGJXDK-UHFFFAOYSA-N 0.000 description 3
- IDQNBVFPZMCDDN-UHFFFAOYSA-N 2-Amino-4,6-dimethylpyrimidine Chemical compound CC1=CC(C)=NC(N)=N1 IDQNBVFPZMCDDN-UHFFFAOYSA-N 0.000 description 3
- 240000006995 Abutilon theophrasti Species 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- 235000004977 Brassica sinapistrum Nutrition 0.000 description 3
- 241000209200 Bromus Species 0.000 description 3
- 241000209202 Bromus secalinus Species 0.000 description 3
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 3
- 235000016854 Cyperus rotundus Nutrition 0.000 description 3
- 240000003826 Eichhornia crassipes Species 0.000 description 3
- 240000001549 Ipomoea eriocarpa Species 0.000 description 3
- 235000005146 Ipomoea eriocarpa Nutrition 0.000 description 3
- 241001330451 Paspalum notatum Species 0.000 description 3
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 230000001276 controlling effect Effects 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 238000011156 evaluation Methods 0.000 description 3
- RHBMVXBGYGIDJN-UHFFFAOYSA-N furan-2-sulfonamide Chemical compound NS(=O)(=O)C1=CC=CO1 RHBMVXBGYGIDJN-UHFFFAOYSA-N 0.000 description 3
- 238000000227 grinding Methods 0.000 description 3
- 150000002540 isothiocyanates Chemical class 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 238000004806 packaging method and process Methods 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- LJXQPZWIHJMPQQ-UHFFFAOYSA-N pyrimidin-2-amine Chemical compound NC1=NC=CC=N1 LJXQPZWIHJMPQQ-UHFFFAOYSA-N 0.000 description 3
- 239000000377 silicon dioxide Substances 0.000 description 3
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 3
- HFOWWBNMJUVIMH-UHFFFAOYSA-N sulfuryl diisothiocyanate Chemical class S=C=NS(=O)(=O)N=C=S HFOWWBNMJUVIMH-UHFFFAOYSA-N 0.000 description 3
- 229910002029 synthetic silica gel Inorganic materials 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- QVCUKHQDEZNNOC-UHFFFAOYSA-N 1,2-diazabicyclo[2.2.2]octane Chemical compound C1CC2CCN1NC2 QVCUKHQDEZNNOC-UHFFFAOYSA-N 0.000 description 2
- KCZIUKYAJJEIQG-UHFFFAOYSA-N 1,3,5-triazin-2-amine Chemical compound NC1=NC=NC=N1 KCZIUKYAJJEIQG-UHFFFAOYSA-N 0.000 description 2
- JIHQDMXYYFUGFV-UHFFFAOYSA-N 1,3,5-triazine Chemical compound C1=NC=NC=N1 JIHQDMXYYFUGFV-UHFFFAOYSA-N 0.000 description 2
- DHQFDLQYQBYUSK-UHFFFAOYSA-N 1-(2,6-dichlorophenyl)sulfonyl-3-(4,6-dimethylpyrimidin-2-yl)urea Chemical compound CC1=CC(C)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2Cl)Cl)=N1 DHQFDLQYQBYUSK-UHFFFAOYSA-N 0.000 description 2
- UJCPNQJOXHPLBF-UHFFFAOYSA-N 1-(4,6-dimethyl-1,3,5-triazin-2-yl)-3-(2-methylphenyl)sulfonylurea Chemical compound CC1=NC(C)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)C)=N1 UJCPNQJOXHPLBF-UHFFFAOYSA-N 0.000 description 2
- CBKZOXZISANBKR-UHFFFAOYSA-N 1-(benzenesulfonyl)-3-(4,6-dimethylpyrimidin-2-yl)thiourea Chemical compound CC1=CC(C)=NC(NC(=S)NS(=O)(=O)C=2C=CC=CC=2)=N1 CBKZOXZISANBKR-UHFFFAOYSA-N 0.000 description 2
- LALCDSDHLXWTTL-UHFFFAOYSA-N 2-chloro-n-(oxomethylidene)benzenesulfonamide Chemical compound ClC1=CC=CC=C1S(=O)(=O)N=C=O LALCDSDHLXWTTL-UHFFFAOYSA-N 0.000 description 2
- CYEJMVLDXAUOPN-UHFFFAOYSA-N 2-dodecylphenol Chemical compound CCCCCCCCCCCCC1=CC=CC=C1O CYEJMVLDXAUOPN-UHFFFAOYSA-N 0.000 description 2
- CDOUZKKFHVEKRI-UHFFFAOYSA-N 3-bromo-n-[(prop-2-enoylamino)methyl]propanamide Chemical compound BrCCC(=O)NCNC(=O)C=C CDOUZKKFHVEKRI-UHFFFAOYSA-N 0.000 description 2
- 241001290610 Abildgaardia Species 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- 235000007320 Avena fatua Nutrition 0.000 description 2
- 241000209764 Avena fatua Species 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 2
- 244000078782 Brassica arvensis Species 0.000 description 2
- 235000008427 Brassica arvensis Nutrition 0.000 description 2
- 235000006719 Cassia obtusifolia Nutrition 0.000 description 2
- 244000277285 Cassia obtusifolia Species 0.000 description 2
- 241000208296 Datura Species 0.000 description 2
- 244000058871 Echinochloa crus-galli Species 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 241000207783 Ipomoea Species 0.000 description 2
- 235000021506 Ipomoea Nutrition 0.000 description 2
- 239000005909 Kieselgur Substances 0.000 description 2
- 229920001732 Lignosulfonate Polymers 0.000 description 2
- 235000003403 Limnocharis flava Nutrition 0.000 description 2
- 241000209082 Lolium Species 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 241001076438 Oxya japonica Species 0.000 description 2
- 235000011999 Panicum crusgalli Nutrition 0.000 description 2
- 208000012641 Pigmentation disease Diseases 0.000 description 2
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
- 239000004698 Polyethylene Substances 0.000 description 2
- 239000004372 Polyvinyl alcohol Substances 0.000 description 2
- 235000017016 Setaria faberi Nutrition 0.000 description 2
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Classifications
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/47—One nitrogen atom and one oxygen or sulfur atom, e.g. cytosine
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- A—HUMAN NECESSITIES
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- 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
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
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- C07D239/26—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
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- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
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- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
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- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/52—Two oxygen atoms
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- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
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- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/56—One oxygen atom and one sulfur atom
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
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- C07D251/16—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to only one ring carbon atom
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- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
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- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
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- C07D251/40—Nitrogen atoms
- C07D251/42—One nitrogen atom
- C07D251/46—One nitrogen atom with oxygen or sulfur atoms attached to the two other ring carbon atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D253/00—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00
- C07D253/02—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00 not condensed with other rings
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- C07D253/07—1,2,4-Triazines having three double bonds between ring members or between ring members and non-ring members 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
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- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
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- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
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- C07D307/64—Sulfur atoms
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- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
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- C—CHEMISTRY; METALLURGY
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- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
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- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D521/00—Heterocyclic compounds containing unspecified hetero rings
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US67466876A | 1976-04-07 | 1976-04-07 | |
US76991377A | 1977-02-23 | 1977-02-23 | |
US76991277A | 1977-02-23 | 1977-02-23 | |
US76991477A | 1977-02-23 | 1977-02-23 |
Publications (2)
Publication Number | Publication Date |
---|---|
JPS52122384A JPS52122384A (en) | 1977-10-14 |
JPS6236029B2 true JPS6236029B2 (US07935154-20110503-C00006.png) | 1987-08-05 |
Family
ID=27505360
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP3906277A Granted JPS52122384A (en) | 1976-04-07 | 1977-04-07 | Nn*heterocyclic aminocarbonyl*aryl sulfonamide and agricultural chemicals containing same |
Country Status (13)
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS63197526U (US07935154-20110503-C00006.png) * | 1987-06-12 | 1988-12-20 |
Families Citing this family (202)
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DK358778A (da) * | 1977-09-19 | 1979-03-20 | Du Pont | Herbicide sulfonamider |
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US4339266A (en) * | 1977-10-06 | 1982-07-13 | E. I. Du Pont De Nemours And Company | Herbicidal sulfonamides |
DK401978A (da) * | 1977-10-06 | 1979-04-07 | Du Pont | Herbicide sulfonamider |
US4191553A (en) * | 1978-03-02 | 1980-03-04 | E. I. Du Pont De Nemours And Company | Herbicidal sulfamates |
US4755216A (en) * | 1978-05-30 | 1988-07-05 | E. I. Du Pont De Nemours And Company | Agricultural sulfonamides |
US4564384A (en) * | 1978-05-30 | 1986-01-14 | E. I. Du Pont De Nemours And Company | Agricultural sulfonamides |
DK168779A (da) * | 1978-05-30 | 1979-12-01 | Du Pont | Agrikulturelle carbaminidothioater |
US4383113A (en) | 1978-05-30 | 1983-05-10 | E. I. Du Pont De Nemours And Company | Agricultural sulfonamides |
US4592978A (en) * | 1979-11-30 | 1986-06-03 | E. I. Du Pont De Nemours And Company | Agricultural sulfonamides |
US4394506A (en) | 1978-05-30 | 1983-07-19 | E. I. Du Pont De Nemours And Company | Agricultural sulfonamides |
DK349479A (da) * | 1978-09-27 | 1980-03-28 | Du Pont | Sulfonamidderivater og deres anvendelse til regulering af plantevaekst |
US4684395A (en) * | 1978-09-27 | 1987-08-04 | E. I. Du Pont De Nemours And Company | Agriculture sulfonamides |
US4501607A (en) * | 1978-09-27 | 1985-02-26 | E. I. Du Pont De Nemours And Company | Herbicidal triazine sulfonamides |
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DK468979A (da) * | 1978-12-04 | 1980-06-05 | Du Pont | Agrikulturelle pyridinsulfonamider |
DK37880A (da) * | 1979-02-22 | 1980-08-23 | Du Pont | Herbicide sulfonamider |
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DK259280A (da) * | 1979-07-20 | 1981-01-21 | Du Pont | Herbicide sulfonamider |
US4452628A (en) * | 1979-07-26 | 1984-06-05 | E. I. Du Pont De Nemours And Company | Herbicidal sulfonamides |
US4301286A (en) * | 1979-08-20 | 1981-11-17 | E. I. Du Pont De Nemours And Company | Herbicidal O-alkyl sulfonylisoureas |
US4293330A (en) * | 1979-10-09 | 1981-10-06 | E. I. Du Pont De Nemours And Company | Herbicidal N-(pyridinylaminocarbonyl)benzenesulfonamides |
DK469179A (da) * | 1979-10-22 | 1981-04-23 | Du Pont | Agrikulturelle pyridinsulfonylsothiourinstoffer |
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US4892946A (en) * | 1979-11-30 | 1990-01-09 | E. I. Du Pont De Nemours And Company | Agricultural sulfonamides |
DK172396B1 (da) * | 1979-11-30 | 1998-05-18 | Du Pont | Thiophencarboxylsyrederivater, middel til bekæmpelse af væksten af uønsket vegetation, fremgangsmåde til bekæmpelse af uønsket vegetation samt mellemprodukter til fremstilling af de nævnte derivater |
US4370479A (en) * | 1979-11-30 | 1983-01-25 | E. I. Du Pont De Nemours And Company | Herbicidal sulfonamides |
DK465580A (da) * | 1979-11-30 | 1981-05-31 | Du Pont | Sulfonamider og deres anvendelse i prae- og postemergens-herbicider og eller plantevaekstreguleringsmidler |
US4339267A (en) | 1980-01-18 | 1982-07-13 | E. I. Du Pont De Nemours And Company | Herbicidal sulfonamides |
BR8102529A (pt) * | 1980-04-29 | 1982-01-05 | Du Pont | Compostos e composicoes herbicidas ou adequados ao controle do crescimento de vegetacao indesejavel e seus processos de preparacao;processo para o controle do crescimento de vegetacao indesejavel |
US4443244A (en) * | 1980-05-19 | 1984-04-17 | E. I. Du Pont De Nemours And Company | Herbicidal sulfonamides |
US4398939A (en) * | 1980-06-03 | 1983-08-16 | E. I. Du Pont De Nemours And Company | Herbicidal thiophenesulfonamides |
US4368069A (en) * | 1980-07-11 | 1983-01-11 | E. I. Du Pont De Nemours And Company | Herbicidal sulfonamides |
US4348219A (en) * | 1980-07-11 | 1982-09-07 | E. I. Du Pont De Nemours And Company | Herbicidal sulfonamides |
US4348220A (en) * | 1980-07-11 | 1982-09-07 | E. I. Du Pont De Nemours And Company | Herbicidal sulfonamides |
JPS5740472A (en) * | 1980-07-11 | 1982-03-06 | Du Pont | Herbicidal sulfonamides |
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US4394153A (en) * | 1980-07-11 | 1983-07-19 | E. I. Du Pont De Nemours And Company | Herbicidal aryl esters of N-[(heterocyclic)-aminocarbonyl]sulfamic acid |
US4378991A (en) * | 1980-07-11 | 1983-04-05 | E. I. Du Pont De Nemours And Company | Herbicidal o-aryl or alkarylsulfonylureas |
CH657849A5 (en) * | 1980-07-17 | 1986-09-30 | Ciba Geigy Ag | N-Phenylsulfonyl-N'-pyrimidinyl- and -triazinyl ureas |
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US4391627A (en) * | 1980-07-25 | 1983-07-05 | E. I. Du Pont De Nemours And Company | Herbicidal benzothiophene and benzofuran sulfonamides |
US4460404A (en) * | 1980-09-15 | 1984-07-17 | E. I. Dupont De Nemours And Company | Triazinyl ureas and isoureas |
US4371391A (en) * | 1980-09-15 | 1983-02-01 | E. I. Du Pont De Nemours And Company | Herbicidal sulfonamides |
US4369320A (en) * | 1980-11-03 | 1983-01-18 | E. I. Du Pont De Nemours And Company | N-[Heterocyclicaminocarbonyl]-8-quinolinesulfonamides |
US4343649A (en) * | 1980-11-17 | 1982-08-10 | E. I. Du Pont De Nemours And Company | Herbicide antidotes |
US4492599A (en) * | 1980-12-04 | 1985-01-08 | E. I. Du Pont De Nemours And Company | Herbicidal s-triazines |
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US4441910A (en) * | 1981-03-24 | 1984-04-10 | E. I. Du Pont De Nemours And Company | Thiophene or furan herbicides |
DE3111451A1 (de) * | 1981-03-24 | 1982-10-07 | Hoechst Ag, 6000 Frankfurt | "heterocyclisch substituierte (halogen)alkyl- und alkoxysulfonylharnstoffe, verfahren zu ihrer herstellung und ihre verwendung in der landwirtschaft" |
US4523943A (en) * | 1981-05-04 | 1985-06-18 | E. I. Du Pont De Nemours And Company | Herbicidal N-(heterocyclic)-aminocarbonyl thiophenesulfonamides |
US4534789A (en) * | 1981-05-19 | 1985-08-13 | E. I. Du Pont De Nemours And Company | Herbicidal o-alkylsulfonyloxy- and o-alkylsulfonylaminobenzenesulfonamides |
US4421550A (en) * | 1981-07-10 | 1983-12-20 | E. I. Du Pont De Nemours & Co. | Herbicidal triazole ureas |
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US4836846A (en) * | 1981-07-16 | 1989-06-06 | E. I. Du Pont De Nemours And Company | Herbicidal indole sulfonamides |
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US4764610A (en) * | 1981-07-16 | 1988-08-16 | E. I. Du Pont De Nemours And Company | Herbicidal indole sulfonamides |
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US4494979A (en) * | 1981-07-24 | 1985-01-22 | E. I. Du Pont De Nemours And Company | Benzofuran sulfamates |
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JPS5846071A (ja) * | 1981-09-16 | 1983-03-17 | Nippon Tokushu Noyaku Seizo Kk | 置換フエニルスルホニルウレア誘導体、その中間体、それらの製法、及び除草剤 |
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CN103220911B (zh) | 2010-10-15 | 2017-02-15 | 拜耳知识产权有限责任公司 | Als抑制剂除草剂用于在对als抑制剂除草剂耐受的甜菜植物中防治不想要的植物的用途 |
AU2012251597B2 (en) | 2011-05-04 | 2015-11-05 | Bayer Intellectual Property Gmbh | Use of ALS inhibitor herbicides for control of unwanted vegetation in ALS inhibitor herbicide tolerant Brassica, such as B. napus, plants |
RU2466128C1 (ru) * | 2011-07-26 | 2012-11-10 | Владимир Веняминович Андронников | Способ получения гранулированного водорастворимого гербицидного препарата на основе диэтилэтаноламинных и щелочных солей арилсульфонилмочевин |
UA115577C2 (uk) | 2012-12-13 | 2017-11-27 | Байєр Кропсайєнс Акцієнгезелльшафт | Застосування гербіцидів на основі інгібітору als для контролю небажаної рослинності в посівах, стійких до гербіцидів, на основі інгібітору als рослин beta vulgaris |
CN103444728B (zh) * | 2013-08-01 | 2016-05-11 | 广东中迅农科股份有限公司 | 一种含有双氟磺草胺和苯氧羧酸类除草剂的组合物 |
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Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR1468747A (fr) * | 1965-07-19 | 1967-02-10 | Benzène-sulfonyl-1 (pyrimidyl-2)-3 urées |
-
1977
- 1977-04-06 OA OA56129A patent/OA05625A/xx unknown
- 1977-04-06 NL NL7703809A patent/NL7703809A/xx not_active Application Discontinuation
- 1977-04-06 CA CA275,660A patent/CA1082189A/en not_active Expired
- 1977-04-07 AU AU24066/77A patent/AU510056B2/en not_active Expired
- 1977-04-07 GB GB14900/77A patent/GB1561120A/en not_active Expired
- 1977-04-07 AT AT246377A patent/AT357359B/de not_active IP Right Cessation
- 1977-04-07 LU LU77081A patent/LU77081A1/xx unknown
- 1977-04-07 BE BE176530A patent/BE853374A/xx not_active IP Right Cessation
- 1977-04-07 JP JP3906277A patent/JPS52122384A/ja active Granted
- 1977-04-07 DE DE19772715786 patent/DE2715786A1/de active Granted
- 1977-04-07 CH CH447277A patent/CH632643A5/de not_active IP Right Cessation
- 1977-04-07 AU AU24065/77A patent/AU511370B2/en not_active Expired
- 1977-04-07 GB GB14903/77A patent/GB1560918A/en not_active Expired
- 1977-04-07 FR FR7710599A patent/FR2403337A1/fr active Granted
- 1977-08-15 US US05/824,805 patent/US4127405A/en not_active Expired - Lifetime
- 1977-09-01 US US05/829,823 patent/US4120691A/en not_active Expired - Lifetime
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS63197526U (US07935154-20110503-C00006.png) * | 1987-06-12 | 1988-12-20 |
Also Published As
Publication number | Publication date |
---|---|
CA1082189A (en) | 1980-07-22 |
DE2715786C2 (US07935154-20110503-C00006.png) | 1987-11-05 |
NL7703809A (nl) | 1977-10-11 |
BE853374A (fr) | 1977-10-07 |
JPS52122384A (en) | 1977-10-14 |
DE2715786A1 (de) | 1977-10-13 |
AT357359B (de) | 1980-07-10 |
AU2406677A (en) | 1978-10-12 |
US4120691A (en) | 1978-10-17 |
AU2406577A (en) | 1978-10-12 |
US4127405A (en) | 1978-11-28 |
OA05625A (fr) | 1981-04-30 |
CH632643A5 (de) | 1982-10-29 |
AU511370B2 (en) | 1980-08-14 |
GB1561120A (en) | 1980-02-13 |
LU77081A1 (US07935154-20110503-C00006.png) | 1977-12-01 |
ATA246377A (de) | 1979-11-15 |
GB1560918A (en) | 1980-02-13 |
FR2403337B1 (US07935154-20110503-C00006.png) | 1983-05-27 |
AU510056B2 (en) | 1980-06-05 |
FR2403337A1 (fr) | 1979-04-13 |
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