JPH03500165A - 除草性ピリジンスルフオニルウレア類 - Google Patents

除草性ピリジンスルフオニルウレア類

Info

Publication number: JPH03500165A
Authority: JP; Japan
Prior art keywords: compound; alkyl; och3; tables; haloalkyl
Prior art date: 1987-08-28
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.): Pending

Application number

JP63504950A

Other languages

English (en)

Japanese (ja)

Inventor

リアン，ポール・シアオ‐ツエン

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

EIDP Inc

Original Assignee

EI Du Pont de Nemours and Co

Priority date (The priority date 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 date listed.)

1987-08-28

Filing date

1988-06-01

Publication date

1991-01-17

1987-08-28 Priority claimed from US07/090,889 external-priority patent/US4808721A/en

1987-09-25 Priority claimed from US07/101,148 external-priority patent/US4774337A/en

1988-06-01 Application filed by EI Du Pont de Nemours and Co filed Critical EI Du Pont de Nemours and Co

1991-01-17 Publication of JPH03500165A publication Critical patent/JPH03500165A/ja

Status Pending legal-status Critical Current

Links

229940100389 Sulfonylurea Drugs 0.000 title claims description 9
230000002363 herbicidal effect Effects 0.000 title description 29
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 title description 15
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 title description 8
150000001875 compounds Chemical class 0.000 claims description 421
125000000217 alkyl group Chemical group 0.000 claims description 82
-1 CC2H5 Chemical group 0.000 claims description 59
238000000034 method Methods 0.000 claims description 43
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 43
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 39
239000000203 mixture Substances 0.000 claims description 39
241000196324 Embryophyta Species 0.000 claims description 37
125000001188 haloalkyl group Chemical group 0.000 claims description 36
239000007787 solid Substances 0.000 claims description 34
240000008042 Zea mays Species 0.000 claims description 30
239000000126 substance Substances 0.000 claims description 30
235000002017 Zea mays subsp mays Nutrition 0.000 claims description 29
235000005824 Zea mays ssp. parviglumis Nutrition 0.000 claims description 27
229910052799 carbon Inorganic materials 0.000 claims description 27
235000005822 corn Nutrition 0.000 claims description 27
125000003545 alkoxy group Chemical group 0.000 claims description 22
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 18
125000004414 alkyl thio group Chemical group 0.000 claims description 16
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 16
229910052731 fluorine Inorganic materials 0.000 claims description 14
239000007788 liquid Substances 0.000 claims description 14
241000894007 species Species 0.000 claims description 14
239000004094 surface-active agent Substances 0.000 claims description 14
125000003342 alkenyl group Chemical group 0.000 claims description 13
125000000304 alkynyl group Chemical group 0.000 claims description 13
229910052736 halogen Inorganic materials 0.000 claims description 13
150000002367 halogens Chemical class 0.000 claims description 13
150000003839 salts Chemical class 0.000 claims description 13
230000008635 plant growth Effects 0.000 claims description 12
125000004966 cyanoalkyl group Chemical group 0.000 claims description 11
125000000753 cycloalkyl group Chemical group 0.000 claims description 11
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 10
125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 9
125000005149 cycloalkylsulfinyl group Chemical group 0.000 claims description 9
125000005366 cycloalkylthio group Chemical group 0.000 claims description 9
230000012010 growth Effects 0.000 claims description 9
229910052717 sulfur Inorganic materials 0.000 claims description 9
229910052760 oxygen Inorganic materials 0.000 claims description 8
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 7
125000003282 alkyl amino group Chemical group 0.000 claims description 7
125000005144 cycloalkylsulfonyl group Chemical group 0.000 claims description 7
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
125000004995 haloalkylthio group Chemical group 0.000 claims description 7
229910052794 bromium Inorganic materials 0.000 claims description 6
125000004183 alkoxy alkyl group Chemical group 0.000 claims description 5
125000005109 alkynylthio group Chemical group 0.000 claims description 5
125000004438 haloalkoxy group Chemical group 0.000 claims description 5
229910052740 iodine Inorganic materials 0.000 claims description 5
JNCMHMUGTWEVOZ-UHFFFAOYSA-N F[CH]F Chemical compound F[CH]F JNCMHMUGTWEVOZ-UHFFFAOYSA-N 0.000 claims description 4
108010081348 HRT1 protein Hairy Proteins 0.000 claims description 4
102100021881 Hairy/enhancer-of-split related with YRPW motif protein 1 Human genes 0.000 claims description 4
125000005108 alkenylthio group Chemical group 0.000 claims description 4
125000006350 alkyl thio alkyl group Chemical group 0.000 claims description 4
125000005134 alkynylsulfinyl group Chemical group 0.000 claims description 4
125000004432 carbon atom Chemical group C* 0.000 claims description 4
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 4
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 3
125000003302 alkenyloxy group Chemical group 0.000 claims description 3
125000005136 alkenylsulfinyl group Chemical group 0.000 claims description 3
125000005137 alkenylsulfonyl group Chemical group 0.000 claims description 3
125000005083 alkoxyalkoxy group Chemical group 0.000 claims description 3
125000004687 alkyl sulfinyl alkyl group Chemical group 0.000 claims description 3
125000005139 alkynylsulfonyl group Chemical group 0.000 claims description 3
239000011630 iodine Substances 0.000 claims description 3
229910052757 nitrogen Inorganic materials 0.000 claims description 3
229910052727 yttrium Inorganic materials 0.000 claims description 3
150000001540 azides Chemical class 0.000 claims description 2
AOJDZKCUAATBGE-UHFFFAOYSA-N bromomethane Chemical compound Br[CH2] AOJDZKCUAATBGE-UHFFFAOYSA-N 0.000 claims description 2
229910052801 chlorine Inorganic materials 0.000 claims description 2
125000004980 cyclopropylene group Chemical group 0.000 claims description 2
125000005843 halogen group Chemical group 0.000 claims description 2
239000010903 husk Substances 0.000 claims description 2
125000004001 thioalkyl group Chemical group 0.000 claims description 2
239000003701 inert diluent Substances 0.000 claims 16
125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 12
125000004768 (C1-C4) alkylsulfinyl group Chemical group 0.000 claims 11
125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims 11
230000002401 inhibitory effect Effects 0.000 claims 8
125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims 7
229910006074 SO2NH2 Inorganic materials 0.000 claims 5
125000000565 sulfonamide group Chemical group 0.000 claims 5
125000006559 (C1-C3) alkylamino group Chemical group 0.000 claims 3
125000004793 2,2,2-trifluoroethoxy group Chemical group FC(CO*)(F)F 0.000 claims 3
101100054666 Streptomyces halstedii sch3 gene Proteins 0.000 claims 3
XSXHWVKGUXMUQE-UHFFFAOYSA-N osmium dioxide Inorganic materials O=[Os]=O XSXHWVKGUXMUQE-UHFFFAOYSA-N 0.000 claims 3
125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims 2
125000004771 (C1-C4) haloalkylsulfinyl group Chemical group 0.000 claims 2
125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 2
125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims 2
125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims 2
125000006519 CCH3 Chemical group 0.000 claims 2
125000004688 alkyl sulfonyl alkyl group Chemical group 0.000 claims 2
WBLIXGSTEMXDSM-UHFFFAOYSA-N chloromethane Chemical compound Cl[CH2] WBLIXGSTEMXDSM-UHFFFAOYSA-N 0.000 claims 2
125000004441 haloalkylsulfonyl group Chemical group 0.000 claims 2
125000004455 (C1-C3) alkylthio group Chemical group 0.000 claims 1
HTEDUHDEKWTKTN-UHFFFAOYSA-N 1-(4,6-dimethoxypyrimidin-2-yl)-3-(3-propylsulfinylpyridin-2-yl)sulfonylurea Chemical compound CCCS(=O)C1=CC=CN=C1S(=O)(=O)NC(=O)NC1=NC(OC)=CC(OC)=N1 HTEDUHDEKWTKTN-UHFFFAOYSA-N 0.000 claims 1
AWZHAXAIAULKCK-UHFFFAOYSA-N 1-(4,6-dimethoxypyrimidin-2-yl)-3-(3-propylsulfonylpyridin-2-yl)sulfonylurea Chemical compound CCCS(=O)(=O)C1=CC=CN=C1S(=O)(=O)NC(=O)NC1=NC(OC)=CC(OC)=N1 AWZHAXAIAULKCK-UHFFFAOYSA-N 0.000 claims 1
GOHGVWUJJPYTMQ-UHFFFAOYSA-N 1-(4,6-dimethoxypyrimidin-2-yl)-3-[3-(ethylsulfamoyl)pyridin-2-yl]sulfonylurea Chemical compound CCNS(=O)(=O)C1=CC=CN=C1S(=O)(=O)NC(=O)NC1=NC(OC)=CC(OC)=N1 GOHGVWUJJPYTMQ-UHFFFAOYSA-N 0.000 claims 1
BCYOIXFWQAQDPZ-UHFFFAOYSA-N 1-(4,6-dimethoxypyrimidin-2-yl)-3-[3-(methylsulfamoyl)pyridin-2-yl]sulfonylurea Chemical compound CNS(=O)(=O)C1=CC=CN=C1S(=O)(=O)NC(=O)NC1=NC(OC)=CC(OC)=N1 BCYOIXFWQAQDPZ-UHFFFAOYSA-N 0.000 claims 1
125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims 1
241000065675 Cyclops Species 0.000 claims 1
241001024304 Mino Species 0.000 claims 1
JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims 1
MGBBHGRNUFGTMS-UHFFFAOYSA-N [2-[(4,6-dimethoxypyrimidin-2-yl)carbamoylsulfamoyl]pyridin-3-yl] methanesulfonate Chemical compound COC1=CC(OC)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CN=2)OS(C)(=O)=O)=N1 MGBBHGRNUFGTMS-UHFFFAOYSA-N 0.000 claims 1
230000003796 beauty Effects 0.000 claims 1
125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims 1
125000004372 methylthioethyl group Chemical group [H]C([H])([H])SC([H])([H])C([H])([H])* 0.000 claims 1
125000004092 methylthiomethyl group Chemical group [H]C([H])([H])SC([H])([H])* 0.000 claims 1
239000001301 oxygen Substances 0.000 claims 1
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 1
244000062793 Sorghum vulgare Species 0.000 description 56
235000007319 Avena orientalis Nutrition 0.000 description 51
240000001549 Ipomoea eriocarpa Species 0.000 description 50
235000005146 Ipomoea eriocarpa Nutrition 0.000 description 50
238000006243 chemical reaction Methods 0.000 description 49
244000075850 Avena orientalis Species 0.000 description 46
235000007558 Avena sp Nutrition 0.000 description 46
240000005979 Hordeum vulgare Species 0.000 description 45
235000007340 Hordeum vulgare Nutrition 0.000 description 45
240000007594 Oryza sativa Species 0.000 description 40
235000007164 Oryza sativa Nutrition 0.000 description 40
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 39
235000011684 Sorghum saccharatum Nutrition 0.000 description 38
239000000243 solution Substances 0.000 description 37
241000219310 Beta vulgaris subsp. vulgaris Species 0.000 description 33
235000021536 Sugar beet Nutrition 0.000 description 33
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 33
241001355178 Setaria faberi Species 0.000 description 32
235000019713 millet Nutrition 0.000 description 31
229920000742 Cotton Polymers 0.000 description 29
235000017016 Setaria faberi Nutrition 0.000 description 29
238000004519 manufacturing process Methods 0.000 description 29
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 28
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 26
239000000047 product Substances 0.000 description 26
229940124530 sulfonamide Drugs 0.000 description 25
150000003456 sulfonamides Chemical class 0.000 description 25
238000005481 NMR spectroscopy Methods 0.000 description 24
235000010469 Glycine max Nutrition 0.000 description 22
244000068988 Glycine max Species 0.000 description 22
235000009566 rice Nutrition 0.000 description 21
241000209140 Triticum Species 0.000 description 19
235000021307 Triticum Nutrition 0.000 description 19
229910052739 hydrogen Inorganic materials 0.000 description 18
244000025254 Cannabis sativa Species 0.000 description 17
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 17
230000035784 germination Effects 0.000 description 16
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 15
240000006394 Sorghum bicolor Species 0.000 description 14
239000002253 acid Substances 0.000 description 14
238000011282 treatment Methods 0.000 description 14
240000006694 Stellaria media Species 0.000 description 13
125000004644 alkyl sulfinyl group Chemical group 0.000 description 13
229910052943 magnesium sulfate Inorganic materials 0.000 description 13
235000019341 magnesium sulphate Nutrition 0.000 description 13
238000003756 stirring Methods 0.000 description 13
125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 12
239000004615 ingredient Substances 0.000 description 12
239000000725 suspension Substances 0.000 description 12
239000012299 nitrogen atmosphere Substances 0.000 description 11
239000012044 organic layer Substances 0.000 description 11
239000002245 particle Substances 0.000 description 11
239000002904 solvent Substances 0.000 description 11
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 10
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 10
239000012267 brine Substances 0.000 description 10
239000011521 glass Substances 0.000 description 10
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 10
241000234282 Allium Species 0.000 description 9
235000002732 Allium cepa var. cepa Nutrition 0.000 description 9
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 9
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 9
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
239000003921 oil Substances 0.000 description 9
235000019198 oils Nutrition 0.000 description 9
238000002360 preparation method Methods 0.000 description 9
YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 9
240000008444 Celtis occidentalis Species 0.000 description 8
235000018962 Celtis occidentalis Nutrition 0.000 description 8
244000152970 Digitaria sanguinalis Species 0.000 description 8
235000010823 Digitaria sanguinalis Nutrition 0.000 description 8
235000002248 Setaria viridis Nutrition 0.000 description 8
240000003768 Solanum lycopersicum Species 0.000 description 8
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 8
239000011575 calcium Substances 0.000 description 8
230000000694 effects Effects 0.000 description 8
150000002148 esters Chemical class 0.000 description 8
238000003818 flash chromatography Methods 0.000 description 8
239000004009 herbicide Substances 0.000 description 8
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
241000219198 Brassica Species 0.000 description 7
235000011331 Brassica Nutrition 0.000 description 7
235000001602 Digitaria X umfolozi Nutrition 0.000 description 7
235000017898 Digitaria ciliaris Nutrition 0.000 description 7
235000005476 Digitaria cruciata Nutrition 0.000 description 7
235000006830 Digitaria didactyla Nutrition 0.000 description 7
235000005804 Digitaria eriantha ssp. eriantha Nutrition 0.000 description 7
235000014716 Eleusine indica Nutrition 0.000 description 7
235000007688 Lycopersicon esculentum Nutrition 0.000 description 7
235000013939 Malva Nutrition 0.000 description 7
240000000982 Malva neglecta Species 0.000 description 7
235000000060 Malva neglecta Nutrition 0.000 description 7
240000003461 Setaria viridis Species 0.000 description 7
239000002585 base Substances 0.000 description 7
230000015572 biosynthetic process Effects 0.000 description 7
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 7
238000005507 spraying Methods 0.000 description 7
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
241000209761 Avena Species 0.000 description 6
241000282994 Cervidae Species 0.000 description 6
LVDRREOUMKACNJ-BKMJKUGQSA-N N-[(2R,3S)-2-(4-chlorophenyl)-1-(1,4-dimethyl-2-oxoquinolin-7-yl)-6-oxopiperidin-3-yl]-2-methylpropane-1-sulfonamide Chemical compound CC(C)CS(=O)(=O)N[C@H]1CCC(=O)N([C@@H]1c1ccc(Cl)cc1)c1ccc2c(C)cc(=O)n(C)c2c1 LVDRREOUMKACNJ-BKMJKUGQSA-N 0.000 description 6
AVYVHIKSFXVDBG-UHFFFAOYSA-N N-benzyl-N-hydroxy-2,2-dimethylbutanamide Chemical compound C(C1=CC=CC=C1)N(C(C(CC)(C)C)=O)O AVYVHIKSFXVDBG-UHFFFAOYSA-N 0.000 description 6
JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 description 6
235000010086 Setaria viridis var. viridis Nutrition 0.000 description 6
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 6
244000061456 Solanum tuberosum Species 0.000 description 6
UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 6
239000000460 chlorine Substances 0.000 description 6
239000002689 soil Substances 0.000 description 6
150000003568 thioethers Chemical class 0.000 description 6
241000208296 Datura Species 0.000 description 5
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 5
235000002595 Solanum tuberosum Nutrition 0.000 description 5
239000003085 diluting agent Substances 0.000 description 5
239000008187 granular material Substances 0.000 description 5
239000000463 material Substances 0.000 description 5
239000010451 perlite Substances 0.000 description 5
235000019362 perlite Nutrition 0.000 description 5
230000004044 response Effects 0.000 description 5
239000011734 sodium Substances 0.000 description 5
229910052708 sodium Inorganic materials 0.000 description 5
238000003786 synthesis reaction Methods 0.000 description 5
YQOLEILXOBUDMU-KRWDZBQOSA-N (4R)-5-[(6-bromo-3-methyl-2-pyrrolidin-1-ylquinoline-4-carbonyl)amino]-4-(2-chlorophenyl)pentanoic acid Chemical compound CC1=C(C2=C(C=CC(=C2)Br)N=C1N3CCCC3)C(=O)NC[C@H](CCC(=O)O)C4=CC=CC=C4Cl YQOLEILXOBUDMU-KRWDZBQOSA-N 0.000 description 4
WGFNXGPBPIJYLI-UHFFFAOYSA-N 2,6-difluoro-3-[(3-fluorophenyl)sulfonylamino]-n-(3-methoxy-1h-pyrazolo[3,4-b]pyridin-5-yl)benzamide Chemical compound C1=C2C(OC)=NNC2=NC=C1NC(=O)C(C=1F)=C(F)C=CC=1NS(=O)(=O)C1=CC=CC(F)=C1 WGFNXGPBPIJYLI-UHFFFAOYSA-N 0.000 description 4
PAYROHWFGZADBR-UHFFFAOYSA-N 2-[[4-amino-5-(5-iodo-4-methoxy-2-propan-2-ylphenoxy)pyrimidin-2-yl]amino]propane-1,3-diol Chemical compound C1=C(I)C(OC)=CC(C(C)C)=C1OC1=CN=C(NC(CO)CO)N=C1N PAYROHWFGZADBR-UHFFFAOYSA-N 0.000 description 4
VVCMGAUPZIKYTH-VGHSCWAPSA-N 2-acetyloxybenzoic acid;[(2s,3r)-4-(dimethylamino)-3-methyl-1,2-diphenylbutan-2-yl] propanoate;1,3,7-trimethylpurine-2,6-dione Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O.CN1C(=O)N(C)C(=O)C2=C1N=CN2C.C([C@](OC(=O)CC)([C@H](C)CN(C)C)C=1C=CC=CC=1)C1=CC=CC=C1 VVCMGAUPZIKYTH-VGHSCWAPSA-N 0.000 description 4
MTAODLNXWYIKSO-UHFFFAOYSA-N 2-fluoropyridine Chemical class FC1=CC=CC=N1 MTAODLNXWYIKSO-UHFFFAOYSA-N 0.000 description 4
DQAZPZIYEOGZAF-UHFFFAOYSA-N 4-ethyl-n-[4-(3-ethynylanilino)-7-methoxyquinazolin-6-yl]piperazine-1-carboxamide Chemical compound C1CN(CC)CCN1C(=O)NC(C(=CC1=NC=N2)OC)=CC1=C2NC1=CC=CC(C#C)=C1 DQAZPZIYEOGZAF-UHFFFAOYSA-N 0.000 description 4
IJRKLHTZAIFUTB-UHFFFAOYSA-N 5-nitro-2-(2-phenylethylamino)benzoic acid Chemical compound OC(=O)C1=CC([N+]([O-])=O)=CC=C1NCCC1=CC=CC=C1 IJRKLHTZAIFUTB-UHFFFAOYSA-N 0.000 description 4
RSIWALKZYXPAGW-NSHDSACASA-N 6-(3-fluorophenyl)-3-methyl-7-[(1s)-1-(7h-purin-6-ylamino)ethyl]-[1,3]thiazolo[3,2-a]pyrimidin-5-one Chemical compound C=1([C@@H](NC=2C=3N=CNC=3N=CN=2)C)N=C2SC=C(C)N2C(=O)C=1C1=CC=CC(F)=C1 RSIWALKZYXPAGW-NSHDSACASA-N 0.000 description 4
235000006719 Cassia obtusifolia Nutrition 0.000 description 4
244000277285 Cassia obtusifolia Species 0.000 description 4
241000192043 Echinochloa Species 0.000 description 4
QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 4
244000248416 Fagopyrum cymosum Species 0.000 description 4
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LPOIGVZLNWEGJG-UHFFFAOYSA-N n-benzyl-5-(4-methylpiperazin-1-yl)-2-nitroaniline Chemical compound C1CN(C)CCN1C1=CC=C([N+]([O-])=O)C(NCC=2C=CC=CC=2)=C1 LPOIGVZLNWEGJG-UHFFFAOYSA-N 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
229930014626 natural product Natural products 0.000 description 1
IOMMMLWIABWRKL-WUTDNEBXSA-N nazartinib Chemical compound C1N(C(=O)/C=C/CN(C)C)CCCC[C@H]1N1C2=C(Cl)C=CC=C2N=C1NC(=O)C1=CC=NC(C)=C1 IOMMMLWIABWRKL-WUTDNEBXSA-N 0.000 description 1
229960003512 nicotinic acid Drugs 0.000 description 1
239000011664 nicotinic acid Substances 0.000 description 1
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
230000000269 nucleophilic effect Effects 0.000 description 1
239000010502 orange oil Substances 0.000 description 1
239000012860 organic pigment Substances 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
AHLBNYSZXLDEJQ-FWEHEUNISA-N orlistat Chemical compound CCCCCCCCCCC[C@H](OC(=O)[C@H](CC(C)C)NC=O)C[C@@H]1OC(=O)[C@H]1CCCCCC AHLBNYSZXLDEJQ-FWEHEUNISA-N 0.000 description 1
UNAHYJYOSSSJHH-UHFFFAOYSA-N oryzalin Chemical compound CCCN(CCC)C1=C([N+]([O-])=O)C=C(S(N)(=O)=O)C=C1[N+]([O-])=O UNAHYJYOSSSJHH-UHFFFAOYSA-N 0.000 description 1
239000007800 oxidant agent Substances 0.000 description 1
BSCHIACBONPEOB-UHFFFAOYSA-N oxolane;hydrate Chemical compound O.C1CCOC1 BSCHIACBONPEOB-UHFFFAOYSA-N 0.000 description 1
FIKAKWIAUPDISJ-UHFFFAOYSA-L paraquat dichloride Chemical compound [Cl-].[Cl-].C1=C[N+](C)=CC=C1C1=CC=[N+](C)C=C1 FIKAKWIAUPDISJ-UHFFFAOYSA-L 0.000 description 1
150000004965 peroxy acids Chemical class 0.000 description 1
230000002688 persistence Effects 0.000 description 1
238000005191 phase separation Methods 0.000 description 1
QLFFCLRSMTUBEZ-UHFFFAOYSA-N phosphoric acid;sodium Chemical compound [Na].[Na].OP(O)(O)=O QLFFCLRSMTUBEZ-UHFFFAOYSA-N 0.000 description 1
239000011574 phosphorus Substances 0.000 description 1
230000000704 physical effect Effects 0.000 description 1
SIOXPEMLGUPBBT-UHFFFAOYSA-N picolinic acid Chemical compound OC(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-N 0.000 description 1
239000000049 pigment Substances 0.000 description 1
239000006187 pill Substances 0.000 description 1
239000011505 plaster Substances 0.000 description 1
239000004584 polyacrylic acid Substances 0.000 description 1
229920002451 polyvinyl alcohol Polymers 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
OTYBMLCTZGSZBG-UHFFFAOYSA-L potassium sulfate Chemical compound [K+].[K+].[O-]S([O-])(=O)=O OTYBMLCTZGSZBG-UHFFFAOYSA-L 0.000 description 1
229910052939 potassium sulfate Inorganic materials 0.000 description 1
235000011151 potassium sulphates Nutrition 0.000 description 1
238000012545 processing Methods 0.000 description 1
LFULEKSKNZEWOE-UHFFFAOYSA-N propanil Chemical compound CCC(=O)NC1=CC=C(Cl)C(Cl)=C1 LFULEKSKNZEWOE-UHFFFAOYSA-N 0.000 description 1
QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 description 1
235000014774 prunus Nutrition 0.000 description 1
238000010298 pulverizing process Methods 0.000 description 1
DWJMBQYORXLGAE-UHFFFAOYSA-N pyridine-2-sulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=N1 DWJMBQYORXLGAE-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
150000003230 pyrimidines Chemical class 0.000 description 1
229910052705 radium Inorganic materials 0.000 description 1
239000002994 raw material Substances 0.000 description 1
230000008707 rearrangement Effects 0.000 description 1
238000010992 reflux Methods 0.000 description 1
229910052703 rhodium Inorganic materials 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
210000004894 snout Anatomy 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 1
239000001488 sodium phosphate Substances 0.000 description 1
229910000162 sodium phosphate Inorganic materials 0.000 description 1
235000011008 sodium phosphates Nutrition 0.000 description 1
238000001179 sorption measurement Methods 0.000 description 1
230000000638 stimulation Effects 0.000 description 1
210000002784 stomach Anatomy 0.000 description 1
150000003457 sulfones Chemical class 0.000 description 1
YROXIXLRRCOBKF-UHFFFAOYSA-N sulfonylurea Chemical class OC(=N)N=S(=O)=O YROXIXLRRCOBKF-UHFFFAOYSA-N 0.000 description 1
150000003462 sulfoxides Chemical class 0.000 description 1
229910052815 sulfur oxide Inorganic materials 0.000 description 1
238000004381 surface treatment Methods 0.000 description 1
239000000375 suspending agent Substances 0.000 description 1
239000003826 tablet Substances 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
239000002562 thickening agent Substances 0.000 description 1
238000012546 transfer Methods 0.000 description 1
150000003852 triazoles Chemical class 0.000 description 1
YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
229940035893 uracil Drugs 0.000 description 1
238000005406 washing Methods 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D521/00—Heterocyclic compounds containing unspecified hetero rings
- 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

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)
Pyridine Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)

JP63504950A 1987-08-28 1988-06-01 除草性ピリジンスルフオニルウレア類 Pending JPH03500165A (ja)

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
US07/090,889 US4808721A (en)	1987-04-16	1987-08-28	Herbicidal pyridinesulfonylureas
US090,889		1987-08-28
US07/101,148 US4774337A (en)	1987-04-16	1987-09-25	Herbicidal pyridinesulfonylureas
US101,148		1987-09-25

Publications (1)

Publication Number	Publication Date
JPH03500165A true JPH03500165A (ja)	1991-01-17

Family

ID=26782752

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP63504950A Pending JPH03500165A (ja)	1987-08-28	1988-06-01	除草性ピリジンスルフオニルウレア類

Country Status (4)

Country	Link
JP (1)	JPH03500165A (pl)
BG (1)	BG60563B1 (pl)
PL (1)	PL158414B1 (pl)
WO (1)	WO1989001937A1 (pl)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5235060A (en) *	1991-07-11	1993-08-10	E. I. Du Pont De Nemours And Company	Certain three component ionic substituted pyridine compounds as intermediates for preparation as herbicides

Citations (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS5973583A (ja) *	1982-09-08	1984-04-25	チバ−ガイギ−・アクチエンゲゼルシヤフト	Ｎ↓−ピリジルスルホニル↓−ｎ′↓−ピリミジニル尿素またはｎ↓−ピリジルスルホニル↓−ｎ′↓−トリアジニル尿素、その製造法、並びに除草および植物生長調節用組成物
JPS60139690A (ja) *	1983-12-08	1985-07-24	チバ‐ガイギー　アクチエンゲゼルシヤフト	新規なスルホニル尿素、その製法、並びに除草及び成長調節用組成物

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
MA19797A1 (fr) *	1982-06-14	1983-12-31	Ciba Geigy Ag	N-heterocyclosulfonyl -n- pyrimidinyl et triazinylurees .
US4579583A (en) *	1982-09-08	1986-04-01	Ciba-Geigy Corporation	Novel sulfonylureas
US4689069A (en) *	1984-08-08	1987-08-25	E. I. Du Pont De Nemours And Company	Herbicidal acetylenic pyrimidines and triazines

1988
- 1988-06-01 JP JP63504950A patent/JPH03500165A/ja active Pending
- 1988-06-01 WO PCT/US1988/001754 patent/WO1989001937A1/en not_active Ceased
- 1988-06-03 PL PL1988272848A patent/PL158414B1/pl unknown
1990
- 1990-02-26 BG BG91292A patent/BG60563B1/bg unknown

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS5973583A (ja) *	1982-09-08	1984-04-25	チバ−ガイギ−・アクチエンゲゼルシヤフト	Ｎ↓−ピリジルスルホニル↓−ｎ′↓−ピリミジニル尿素またはｎ↓−ピリジルスルホニル↓−ｎ′↓−トリアジニル尿素、その製造法、並びに除草および植物生長調節用組成物
JPS60139690A (ja) *	1983-12-08	1985-07-24	チバ‐ガイギー　アクチエンゲゼルシヤフト	新規なスルホニル尿素、その製法、並びに除草及び成長調節用組成物

Also Published As

Publication number	Publication date
BG60563B1 (en)	1995-08-28
PL158414B1 (pl)	1992-09-30
PL272848A1 (en)	1989-03-06
WO1989001937A1 (en)	1989-03-09
BG91292A (bg)	1993-12-24

Publication	Publication Date	Title
US4342587A (en)	1982-08-03	Herbicidal pyridinsulfonamides
KR890002084B1 (ko)	1989-06-16	N-페닐설포닐-n'-피리미디닐-및-트리아지닐-우레아의 제조방법
JP2572954B2 (ja)	1997-01-16	除草性ピリジンスルフオニルウレア類
JPH0733740A (ja)	1995-02-03	ピリジンカルボキシアミド誘導体
HU190675B (en)	1986-10-28	Herbicidal and plant growth regulating compositions comprising thiophene-sulfonamide-derivatives
US4302241A (en)	1981-11-24	Agricultural sulfonamides
JPS6391378A (ja)	1988-04-22	アミノピラジノン及びアミノトリアジノン、それらの製造方法並びにそれらを含有する組成物
DK163123B (da)	1992-01-20	Benzensulfonylurinstoffer til anvendelse som herbicider eller plantevaekstregulatorer, praeparat indeholdende dem samt deres anvendelse
JPS5823677A (ja)	1983-02-12	Ｎ−フエニルスルホニル−ｎ′−ピリミジニル−及び−トリアジニル尿素
EP0502740A1 (en)	1992-09-09	Herbicidal pyridine sulfonamide
JP2615228B2 (ja)	1997-05-28	フルオロエトキシアミノトリアジン
IE51689B1 (en)	1987-02-04	Herbicidal sulfonamides
JPH0152389B2 (pl)	1989-11-08
EP0272855B1 (en)	1991-12-11	Herbicidal pyridine sulfonamides
JPH03500165A (ja)	1991-01-17	除草性ピリジンスルフオニルウレア類
US5461024A (en)	1995-10-24	Thiophenesulfonylurea derivatives
JPH02500980A (ja)	1990-04-05	チオフエンスルホンアミド除草剤
US4774337A (en)	1988-09-27	Herbicidal pyridinesulfonylureas
US5102444A (en)	1992-04-07	Herbicidal pyridinesulfonylureas
US5512535A (en)	1996-04-30	Herbicidal pyridinesulfonylureas
US4761173A (en)	1988-08-02	Herbicidal heterocyclic sulfonamides
EP3475273A1 (de)	2019-05-01	3-amino-1,2,4-triazinderivate und deren verwendung zur bekämpfung unerwünschten pflanzenwachstums
JPS62190170A (ja)	1987-08-20	アシル化スルホニルグアニジン類
JPH07502756A (ja)	1995-03-23	新規の除草剤
JPS62286974A (ja)	1987-12-12	Ｎ−フェニルスルホニル尿素、その製造方法並びに該化合物を含有する除草及び植物生長調節剤