AU717425B2 - Substituted thienylsulphonyl (thio) ureas as herbicides - Google Patents

Substituted thienylsulphonyl (thio) ureas as herbicides Download PDF

Info

Publication number: AU717425B2
Authority: AU; Australia
Prior art keywords: general formula; compounds; methyl; substituted; methoxy
Prior art date: 1996-03-07
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.): Ceased

Application number

AU20927/97A

Other languages

English (en)

Other versions

AU2092797A (en

Inventor

Markus Dollinger

Mark Wilhelm Drewes

Ernst-Rudolf F. Gesing

Johannes Rudolf Jansen

Rolf Kirsten

Joachim Kluth

Klaus-Helmut Muller

Ulrich Philipp

Hans-Jochem Riebel

Hans-Joachim Santel

Otto Schallner

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.)

Bayer AG

Original Assignee

Bayer AG

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.)

1996-03-07

Filing date

1997-02-24

Publication date

2000-03-23

1997-02-24 Application filed by Bayer AG filed Critical Bayer AG

1997-09-22 Publication of AU2092797A publication Critical patent/AU2092797A/en

2000-03-23 Application granted granted Critical

2000-03-23 Publication of AU717425B2 publication Critical patent/AU717425B2/en

2017-02-24 Anticipated expiration legal-status Critical

Status Ceased legal-status Critical Current

Links

150000003672 ureas Chemical class 0.000 title description 8
235000013877 carbamide Nutrition 0.000 title description 7
239000004009 herbicide Substances 0.000 title description 6
125000000446 sulfanediyl group Chemical group *S* 0.000 title 1
150000001875 compounds Chemical class 0.000 claims description 71
238000000034 method Methods 0.000 claims description 28
241000196324 Embryophyta Species 0.000 claims description 22
239000000203 mixture Substances 0.000 claims description 18
238000006243 chemical reaction Methods 0.000 claims description 17
150000003839 salts Chemical class 0.000 claims description 9
125000003545 alkoxy group Chemical group 0.000 claims description 8
229910052736 halogen Inorganic materials 0.000 claims description 8
150000002367 halogens Chemical class 0.000 claims description 8
KTFDYVNEGTXQCV-UHFFFAOYSA-N 2-Thiophenesulfonamide Chemical class NS(=O)(=O)C1=CC=CS1 KTFDYVNEGTXQCV-UHFFFAOYSA-N 0.000 claims description 7
239000003085 diluting agent Substances 0.000 claims description 7
230000002363 herbicidal effect Effects 0.000 claims description 6
125000004104 aryloxy group Chemical group 0.000 claims description 5
150000001913 cyanates Chemical class 0.000 claims description 4
239000004606 Fillers/Extenders Substances 0.000 claims description 3
239000004094 surface-active agent Substances 0.000 claims description 2
238000004519 manufacturing process Methods 0.000 claims 2
235000015392 Sesbania grandiflora Nutrition 0.000 claims 1
244000275021 Sesbania grandiflora Species 0.000 claims 1
230000008635 plant growth Effects 0.000 claims 1
-1 cyano- Chemical class 0.000 description 77
238000002360 preparation method Methods 0.000 description 22
125000002496 methyl group Chemical class [H]C([H])([H])* 0.000 description 21
239000004202 carbamide Substances 0.000 description 18
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 16
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 15
YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical group [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 14
239000007858 starting material Substances 0.000 description 14
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
239000001257 hydrogen Substances 0.000 description 13
229910052739 hydrogen Inorganic materials 0.000 description 13
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
125000004432 carbon atom Chemical group C* 0.000 description 10
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 10
239000000460 chlorine Chemical group 0.000 description 9
239000002904 solvent Substances 0.000 description 9
229910052801 chlorine Inorganic materials 0.000 description 8
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 7
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238000009472 formulation Methods 0.000 description 7
150000002431 hydrogen Chemical group 0.000 description 7
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241001101998 Galium Species 0.000 description 6
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 6
229910052794 bromium Inorganic materials 0.000 description 6
230000006378 damage Effects 0.000 description 6
230000000694 effects Effects 0.000 description 6
239000011737 fluorine Chemical group 0.000 description 6
229910052731 fluorine Inorganic materials 0.000 description 6
239000008187 granular material Substances 0.000 description 6
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 6
239000002689 soil Substances 0.000 description 6
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 5
241000743985 Alopecurus Species 0.000 description 5
235000005781 Avena Nutrition 0.000 description 5
244000075850 Avena orientalis Species 0.000 description 5
241000234653 Cyperus Species 0.000 description 5
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 5
125000005843 halogen group Chemical group 0.000 description 5
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 5
238000002844 melting Methods 0.000 description 5
230000008018 melting Effects 0.000 description 5
229910052757 nitrogen Inorganic materials 0.000 description 5
239000000843 powder Substances 0.000 description 5
125000000547 substituted alkyl group Chemical group 0.000 description 5
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241000219318 Amaranthus Species 0.000 description 4
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VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 4
239000005864 Sulphur Chemical group 0.000 description 4
125000003282 alkyl amino group Chemical group 0.000 description 4
125000000217 alkyl group Chemical group 0.000 description 4
125000004414 alkyl thio group Chemical group 0.000 description 4
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
239000011575 calcium Substances 0.000 description 4
239000003795 chemical substances by application Substances 0.000 description 4
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
125000000000 cycloalkoxy group Chemical group 0.000 description 4
125000000753 cycloalkyl group Chemical group 0.000 description 4
125000004663 dialkyl amino group Chemical group 0.000 description 4
125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 4
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 4
238000001914 filtration Methods 0.000 description 4
229910052500 inorganic mineral Inorganic materials 0.000 description 4
235000010755 mineral Nutrition 0.000 description 4
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
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QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 4
239000001301 oxygen Substances 0.000 description 4
229910052760 oxygen Inorganic materials 0.000 description 4
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 4
VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
239000000126 substance Substances 0.000 description 4
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125000002877 alkyl aryl group Chemical group 0.000 description 3
JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 3
239000000969 carrier Substances 0.000 description 3
239000012141 concentrate Substances 0.000 description 3
150000002148 esters Chemical class 0.000 description 3
235000019441 ethanol Nutrition 0.000 description 3
150000002170 ethers Chemical class 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
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239000010695 polyglycol Substances 0.000 description 3
239000000047 product Substances 0.000 description 3
NKFOUKLOIHAFLB-UHFFFAOYSA-N propyl 3-[(4-cyclopropyl-6-methoxypyrimidin-2-yl)carbamoylsulfamoyl]-4-methylthiophene-2-carboxylate Chemical compound C1(CC1)C1=NC(=NC(=C1)OC)NC(=O)NS(=O)(=O)C1=C(SC=C1C)C(=O)OCCC NKFOUKLOIHAFLB-UHFFFAOYSA-N 0.000 description 3
239000007787 solid Substances 0.000 description 3
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NFDXQGNDWIPXQL-UHFFFAOYSA-N 1-cyclooctyldiazocane Chemical compound C1CCCCCCC1N1NCCCCCC1 NFDXQGNDWIPXQL-UHFFFAOYSA-N 0.000 description 2
PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical compound CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 description 2
QDFXRVAOBHEBGJ-UHFFFAOYSA-N 3-(cyclononen-1-yl)-4,5,6,7,8,9-hexahydro-1h-diazonine Chemical compound C1CCCCCCC=C1C1=NNCCCCCC1 QDFXRVAOBHEBGJ-UHFFFAOYSA-N 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
241000209200 Bromus Species 0.000 description 2
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HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
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241000207763 Solanum Species 0.000 description 2
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235000011684 Sorghum saccharatum Nutrition 0.000 description 2
244000062793 Sorghum vulgare Species 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
239000002253 acid Substances 0.000 description 2
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125000004368 propenyl group Chemical class C(=CC)* 0.000 description 1
VXPLXMJHHKHSOA-UHFFFAOYSA-N propham Chemical compound CC(C)OC(=O)NC1=CC=CC=C1 VXPLXMJHHKHSOA-UHFFFAOYSA-N 0.000 description 1
FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
RNVOHKDCPVBJEL-UHFFFAOYSA-N propyl 3-[(4-cyclopropyl-6-methoxy-1,3,5-triazin-2-yl)carbamoylsulfamoyl]-4-methylthiophene-2-carboxylate Chemical compound C1(CC1)C1=NC(=NC(=N1)OC)NC(=O)NS(=O)(=O)C1=C(SC=C1C)C(=O)OCCC RNVOHKDCPVBJEL-UHFFFAOYSA-N 0.000 description 1
RKCPGKQCDRRPRA-UHFFFAOYSA-N propyl 4-ethyl-3-sulfamoylthiophene-2-carboxylate Chemical compound CCCOC(=O)C=1SC=C(CC)C=1S(N)(=O)=O RKCPGKQCDRRPRA-UHFFFAOYSA-N 0.000 description 1
PPTXVSVKUVLIEH-UHFFFAOYSA-N propyl 4-methyl-3-sulfamoylthiophene-2-carboxylate Chemical compound CCCOC(=O)C=1SC=C(C)C=1S(N)(=O)=O PPTXVSVKUVLIEH-UHFFFAOYSA-N 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
NQLVQOSNDJXLKG-UHFFFAOYSA-N prosulfocarb Chemical compound CCCN(CCC)C(=O)SCC1=CC=CC=C1 NQLVQOSNDJXLKG-UHFFFAOYSA-N 0.000 description 1
239000003531 protein hydrolysate Substances 0.000 description 1
229960003351 prussian blue Drugs 0.000 description 1
239000013225 prussian blue Substances 0.000 description 1
239000008262 pumice Substances 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
239000010453 quartz Substances 0.000 description 1
FFSSWMQPCJRCRV-UHFFFAOYSA-N quinclorac Chemical compound ClC1=CN=C2C(C(=O)O)=C(Cl)C=CC2=C1 FFSSWMQPCJRCRV-UHFFFAOYSA-N 0.000 description 1
ALZOLUNSQWINIR-UHFFFAOYSA-N quinmerac Chemical compound OC(=O)C1=C(Cl)C=CC2=CC(C)=CN=C21 ALZOLUNSQWINIR-UHFFFAOYSA-N 0.000 description 1
BACHBFVBHLGWSL-JTQLQIEISA-N rac-diclofop methyl Natural products C1=CC(O[C@@H](C)C(=O)OC)=CC=C1OC1=CC=C(Cl)C=C1Cl BACHBFVBHLGWSL-JTQLQIEISA-N 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
238000010992 reflux Methods 0.000 description 1
239000005871 repellent Substances 0.000 description 1
230000002940 repellent Effects 0.000 description 1
239000011435 rock Substances 0.000 description 1
229910052624 sepiolite Inorganic materials 0.000 description 1
235000019355 sepiolite Nutrition 0.000 description 1
150000004760 silicates Chemical class 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
ODCWYMIRDDJXKW-UHFFFAOYSA-N simazine Chemical compound CCNC1=NC(Cl)=NC(NCC)=N1 ODCWYMIRDDJXKW-UHFFFAOYSA-N 0.000 description 1
MGLWZSOBALDPEK-UHFFFAOYSA-N simetryn Chemical compound CCNC1=NC(NCC)=NC(SC)=N1 MGLWZSOBALDPEK-UHFFFAOYSA-N 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
235000015424 sodium Nutrition 0.000 description 1
239000001632 sodium acetate Substances 0.000 description 1
235000017281 sodium acetate Nutrition 0.000 description 1
ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
235000017550 sodium carbonate Nutrition 0.000 description 1
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
229910000104 sodium hydride Inorganic materials 0.000 description 1
235000011121 sodium hydroxide Nutrition 0.000 description 1
238000009331 sowing Methods 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
238000005507 spraying Methods 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000004548 suspo-emulsion Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
229920002994 synthetic fiber Polymers 0.000 description 1
229920001059 synthetic polymer Polymers 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
IROINLKCQGIITA-UHFFFAOYSA-N terbutryn Chemical compound CCNC1=NC(NC(C)(C)C)=NC(SC)=N1 IROINLKCQGIITA-UHFFFAOYSA-N 0.000 description 1
FZXISNSWEXTPMF-UHFFFAOYSA-N terbutylazine Chemical compound CCNC1=NC(Cl)=NC(NC(C)(C)C)=N1 FZXISNSWEXTPMF-UHFFFAOYSA-N 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
125000003718 tetrahydrofuranyl group Chemical class 0.000 description 1
ZFXYFBGIUFBOJW-UHFFFAOYSA-N theophylline Chemical compound O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 0.000 description 1
229960000278 theophylline Drugs 0.000 description 1
AHTPATJNIAFOLR-UHFFFAOYSA-N thifensulfuron-methyl Chemical group S1C=CC(S(=O)(=O)NC(=O)NC=2N=C(OC)N=C(C)N=2)=C1C(=O)OC AHTPATJNIAFOLR-UHFFFAOYSA-N 0.000 description 1
150000003558 thiocarbamic acid derivatives Chemical class 0.000 description 1
ZWZVWGITAAIFPS-UHFFFAOYSA-N thiophosgene Chemical compound ClC(Cl)=S ZWZVWGITAAIFPS-UHFFFAOYSA-N 0.000 description 1
OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
DQFPEYARZIQXRM-LTGZKZEYSA-N tralkoxydim Chemical compound C1C(=O)C(C(/CC)=N/OCC)=C(O)CC1C1=C(C)C=C(C)C=C1C DQFPEYARZIQXRM-LTGZKZEYSA-N 0.000 description 1
XOPFESVZMSQIKC-UHFFFAOYSA-N triasulfuron Chemical compound COC1=NC(C)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)OCCCl)=N1 XOPFESVZMSQIKC-UHFFFAOYSA-N 0.000 description 1
150000003918 triazines Chemical class 0.000 description 1
YMXOXAPKZDWXLY-QWRGUYRKSA-N tribenuron methyl Chemical group COC(=O)[C@H]1CCCC[C@@H]1S(=O)(=O)NC(=O)N(C)C1=NC(C)=NC(OC)=N1 YMXOXAPKZDWXLY-QWRGUYRKSA-N 0.000 description 1
IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
REEQLXCGVXDJSQ-UHFFFAOYSA-N trichlopyr Chemical compound OC(=O)COC1=NC(Cl)=C(Cl)C=C1Cl REEQLXCGVXDJSQ-UHFFFAOYSA-N 0.000 description 1
ZSDSQXJSNMTJDA-UHFFFAOYSA-N trifluralin Chemical compound CCCN(CCC)C1=C([N+]([O-])=O)C=C(C(F)(F)F)C=C1[N+]([O-])=O ZSDSQXJSNMTJDA-UHFFFAOYSA-N 0.000 description 1
239000002699 waste material Substances 0.000 description 1
238000010626 work up procedure Methods 0.000 description 1
239000011701 zinc Substances 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
- 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D521/00—Heterocyclic compounds containing unspecified hetero rings

Landscapes

Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Health & Medical Sciences (AREA)
Plant Pathology (AREA)
Engineering & Computer Science (AREA)
Dentistry (AREA)
General Health & Medical Sciences (AREA)
Wood Science & Technology (AREA)
Zoology (AREA)
Environmental Sciences (AREA)
Pest Control & Pesticides (AREA)
Agronomy & Crop Science (AREA)
Plural Heterocyclic Compounds (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)

AU20927/97A 1996-03-07 1997-02-24 Substituted thienylsulphonyl (thio) ureas as herbicides Ceased AU717425B2 (en)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
DE19608831A DE19608831A1 (de)	1996-03-07	1996-03-07	Substituierte Thienylsulfonyl(thio)harnstoffe
DE19608831		1996-03-07
PCT/EP1997/000877 WO1997032875A1 (de)	1996-03-07	1997-02-24	Substituierte thienylsulfonyl(thio)harnstoffe als herbizide

Publications (2)

Publication Number	Publication Date
AU2092797A AU2092797A (en)	1997-09-22
AU717425B2 true AU717425B2 (en)	2000-03-23

Family

ID=7787505

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
AU20927/97A Ceased AU717425B2 (en)	1996-03-07	1997-02-24	Substituted thienylsulphonyl (thio) ureas as herbicides

Country Status (9)

Country	Link
EP (1)	EP0885216A1 (pt)
JP (1)	JP2000506146A (pt)
KR (1)	KR19990087494A (pt)
CN (1)	CN1218469A (pt)
AU (1)	AU717425B2 (pt)
BR (1)	BR9708009A (pt)
CA (1)	CA2248290A1 (pt)
DE (1)	DE19608831A1 (pt)
WO (1)	WO1997032875A1 (pt)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
WO2000044227A1 (de) *	1999-01-27	2000-08-03	Aventis Cropscience Gmbh	Formulierung von herbiziden und pflanzenwachstumsregulatoren
DE19963383A1 (de)	1999-12-28	2001-07-05	Aventis Cropscience Gmbh	Formulierung von Herbiziden und Pflanzenwachstumsregulatoren
DE19937118A1 (de) *	1999-08-06	2001-02-08	Bayer Ag	Substituierte Thienyl(amino)sulfonylharnstoffe
TWI782504B (zh)	2020-05-08	2022-11-01	美商美國禮來大藥廠	(三氟甲基)嘧啶-2-胺化合物

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
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
CA1257262A (en) *	1985-05-20	1989-07-11	George Levitt	Herbicidal thiophenesulfonamides
US4877440A (en) *	1985-05-29	1989-10-31	E. I. Du Pont De Nemours And Company	Thiophenesulfonamide herbicides

1996
- 1996-03-07 DE DE19608831A patent/DE19608831A1/de not_active Withdrawn
1997
- 1997-02-24 CN CN97194465A patent/CN1218469A/zh active Pending
- 1997-02-24 CA CA002248290A patent/CA2248290A1/en not_active Abandoned
- 1997-02-24 EP EP97906118A patent/EP0885216A1/de not_active Withdrawn
- 1997-02-24 KR KR1019980706922A patent/KR19990087494A/ko not_active Withdrawn
- 1997-02-24 AU AU20927/97A patent/AU717425B2/en not_active Ceased
- 1997-02-24 JP JP9531404A patent/JP2000506146A/ja active Pending
- 1997-02-24 WO PCT/EP1997/000877 patent/WO1997032875A1/de not_active Ceased
- 1997-02-24 BR BR9708009A patent/BR9708009A/pt unknown

Also Published As

Publication number	Publication date
EP0885216A1 (de)	1998-12-23
WO1997032875A1 (de)	1997-09-12
CN1218469A (zh)	1999-06-02
JP2000506146A (ja)	2000-05-23
BR9708009A (pt)	1999-07-27
DE19608831A1 (de)	1997-09-18
KR19990087494A (ko)	1999-12-27
CA2248290A1 (en)	1997-09-12
AU2092797A (en)	1997-09-22

Legal Events

Date	Code	Title	Description
2000-07-20	FGA	Letters patent sealed or granted (standard patent)
2002-09-26	MK14	Patent ceased section 143(a) (annual fees not paid) or expired

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CA2188580C (en)	2007-09-25	N-cyanoaryl nitrogen heterocycles
CA2134915A1 (en)	1995-05-06	Herbicidal substituted phenylaminosulphonylureas
CA2226669C (en)	2006-10-17	Herbicidal sulphonylamino(thio)carbonyl compounds
US20030162979A1 (en)	2003-08-28	Substituted sulphonylamino(thio)carbonyl compounds
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CA2263548A1 (en)	1998-02-26	5,6-dihydro-[1,4,2]-dioxazin-substituted (hetero)aryl-(oxy-,imino-, alkyl-)-sulphonylamino(thio)carbonyl-heterocyclyl derivatives, their preparation and their use as herbicides
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US5994273A (en)	1999-11-30	Herbicidal or fungicidal sulphonylaminocarbonyltriazolinones with halogenated alk(en)ylthio substituents
US5496793A (en)	1996-03-05	Substituted carbamoyltriazoles
AU717425B2 (en)	2000-03-23	Substituted thienylsulphonyl (thio) ureas as herbicides
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AU718404B2 (en)	2000-04-13	Substituted phenyluracils and their use as herbicides
CA2220494A1 (en)	1996-11-14	Sulphonylamino(thio)carbonyltriazolin(thi)ones with aryloxy or arylthio substituents
US5270288A (en)	1993-12-14	Herbicidal N-azinyl-N'-(2-ethylsulphinyl-phenylsulphonyl)-ureas
AU716994B2 (en)	2000-03-16	Substituted phenyluracils
US5371062A (en)	1994-12-06	Substituted azines
CA2248068C (en)	2006-10-10	Substituted aryl sulphonyl(thio)ureas used as herbicides
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CA2211411C (en)	2006-10-24	Sulphonyl amino(thio)carbonyl-1,2,4-triazolin(thi)one derivatives, the production thereof and the use thereof as herbicides
CA2075407A1 (en)	1993-02-10	N-azinyl-n-(2-methylsulphinyl- phenylsulphonyl)-ureas
CA2110624A1 (en)	1994-06-09	Substituted quinolylsulphonylureas
CA2114699A1 (en)	1994-08-05	Selective herbicides based on n-azinyl-n'-(2-ethylthio- phenylsulphonyl)-ureas
CA2227012A1 (en)	1997-02-06	Substituted aryl sulphonyl amino (thio) carbonyl triazolin(thi)ones