CA2191759C - Formylaminophenylsulfonylurees, leur procede de fabrication et leur utilisation en tant qu'herbicides et regulateurs de croissance des vegetaux - Google Patents

Formylaminophenylsulfonylurees, leur procede de fabrication et leur utilisation en tant qu'herbicides et regulateurs de croissance des vegetaux Download PDF

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Publication number: CA2191759C
Authority: CA; Canada
Prior art keywords: alkyl; general formula; alkoxy; radicals; halogen atom
Prior art date: 1994-06-01
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 - Lifetime

Application number

CA002191759A

Other languages

English (en)

Other versions

CA2191759A1 (fr

Inventor

Gerhard Schnabel

Lothar Willms

Klaus Bauer

Hermann Bieringer

Christopher Rosinger

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 Intellectual Property GmbH

Original Assignee

Hoechst Schering Agrevo GmbH

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.)

1994-06-01

Filing date

1995-05-17

Publication date

2006-10-31

1994-06-01 Priority claimed from DE4419259A external-priority patent/DE4419259A1/de

1995-03-20 Priority claimed from DE1995110078 external-priority patent/DE19510078A1/de

1995-05-17 Application filed by Hoechst Schering Agrevo GmbH filed Critical Hoechst Schering Agrevo GmbH

1995-05-17 Priority claimed from PCT/EP1995/001867 external-priority patent/WO1995032950A1/fr

1995-12-07 Publication of CA2191759A1 publication Critical patent/CA2191759A1/fr

2006-10-31 Application granted granted Critical

2006-10-31 Publication of CA2191759C publication Critical patent/CA2191759C/fr

2015-05-17 Anticipated expiration legal-status Critical

Status Expired - Lifetime legal-status Critical Current

Links

239000004009 herbicide Substances 0.000 title claims abstract description 10
239000005648 plant growth regulator Substances 0.000 title claims abstract description 6
238000002360 preparation method Methods 0.000 title claims description 10
-1 (C2-C6)-alkenyloxy Chemical group 0.000 claims abstract description 69
150000001875 compounds Chemical class 0.000 claims abstract description 46
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 11
238000000034 method Methods 0.000 claims abstract description 11
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims abstract description 9
125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims abstract description 7
229910052717 sulfur Inorganic materials 0.000 claims abstract description 7
125000000882 C2-C6 alkenyl group Chemical group 0.000 claims abstract description 6
125000003601 C2-C6 alkynyl group Chemical group 0.000 claims abstract description 6
125000004430 oxygen atom Chemical group O* 0.000 claims abstract description 6
229940124530 sulfonamide Drugs 0.000 claims abstract description 6
150000003456 sulfonamides Chemical class 0.000 claims abstract description 6
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 5
125000004663 dialkyl amino group Chemical group 0.000 claims abstract description 4
125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims abstract description 3
125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims abstract description 3
125000004434 sulfur atom Chemical group 0.000 claims abstract description 3
125000005843 halogen group Chemical group 0.000 claims abstract 9
125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims abstract 4
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract 3
125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims abstract 2
125000006766 (C2-C6) alkynyloxy group Chemical group 0.000 claims abstract 2
JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims abstract 2
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 69
239000000203 mixture Substances 0.000 claims description 34
150000003254 radicals Chemical class 0.000 claims description 34
238000009472 formulation Methods 0.000 claims description 15
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 15
230000002363 herbicidal effect Effects 0.000 claims description 12
125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 7
125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims description 5
229940100389 Sulfonylurea Drugs 0.000 claims description 5
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 5
230000001276 controlling effect Effects 0.000 claims description 4
125000000623 heterocyclic group Chemical group 0.000 claims description 4
YROXIXLRRCOBKF-UHFFFAOYSA-N sulfonylurea Chemical compound OC(=N)N=S(=O)=O YROXIXLRRCOBKF-UHFFFAOYSA-N 0.000 claims description 4
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
125000006583 (C1-C3) haloalkyl group Chemical group 0.000 claims description 3
NONOKGVFTBWRLD-UHFFFAOYSA-N isocyanatosulfanylimino(oxo)methane Chemical compound O=C=NSN=C=O NONOKGVFTBWRLD-UHFFFAOYSA-N 0.000 claims description 3
XTHPWXDJESJLNJ-UHFFFAOYSA-N sulfurochloridic acid Chemical compound OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 claims description 3
KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims description 2
XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate Chemical compound [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 0.000 claims description 2
QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical compound C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 claims description 2
230000001105 regulatory effect Effects 0.000 claims description 2
125000006526 (C1-C2) alkyl group Chemical group 0.000 claims 1
125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims 1
125000004399 C1-C4 alkenyl group Chemical group 0.000 claims 1
125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims 1
230000008635 plant growth Effects 0.000 claims 1
ZBZJXHCVGLJWFG-UHFFFAOYSA-N trichloromethyl(.) Chemical compound Cl[C](Cl)Cl ZBZJXHCVGLJWFG-UHFFFAOYSA-N 0.000 claims 1
229910052736 halogen Inorganic materials 0.000 abstract description 19
150000002367 halogens Chemical class 0.000 abstract description 18
229930195733 hydrocarbon Natural products 0.000 abstract description 7
239000004215 Carbon black (E152) Substances 0.000 abstract description 6
241001484259 Lacuna Species 0.000 abstract 1
241000196324 Embryophyta Species 0.000 description 35
239000013543 active substance Substances 0.000 description 24
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 21
239000000126 substance Substances 0.000 description 17
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
239000008187 granular material Substances 0.000 description 11
239000002689 soil Substances 0.000 description 11
GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 10
239000000843 powder Substances 0.000 description 10
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 9
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 8
125000004432 carbon atom Chemical group C* 0.000 description 8
241000209510 Liliopsida Species 0.000 description 7
239000002585 base Substances 0.000 description 7
238000006243 chemical reaction Methods 0.000 description 7
244000038559 crop plants Species 0.000 description 7
230000000694 effects Effects 0.000 description 7
239000004495 emulsifiable concentrate Substances 0.000 description 7
239000000839 emulsion Substances 0.000 description 7
241001233957 eudicotyledons Species 0.000 description 7
239000004562 water dispersible granule Substances 0.000 description 7
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
125000003342 alkenyl group Chemical group 0.000 description 6
239000003995 emulsifying agent Substances 0.000 description 6
150000002148 esters Chemical class 0.000 description 6
RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
230000012010 growth Effects 0.000 description 6
239000011734 sodium Substances 0.000 description 6
229910052708 sodium Inorganic materials 0.000 description 6
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 5
125000000217 alkyl group Chemical group 0.000 description 5
125000000304 alkynyl group Chemical group 0.000 description 5
239000000460 chlorine Substances 0.000 description 5
229910052801 chlorine Inorganic materials 0.000 description 5
238000000227 grinding Methods 0.000 description 5
238000002156 mixing Methods 0.000 description 5
239000010695 polyglycol Substances 0.000 description 5
239000002904 solvent Substances 0.000 description 5
238000012360 testing method Methods 0.000 description 5
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 4
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
239000002253 acid Substances 0.000 description 4
150000007513 acids Chemical class 0.000 description 4
239000012141 concentrate Substances 0.000 description 4
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
229910052731 fluorine Inorganic materials 0.000 description 4
239000011737 fluorine Substances 0.000 description 4
238000005469 granulation Methods 0.000 description 4
230000003179 granulation Effects 0.000 description 4
125000001188 haloalkyl group Chemical group 0.000 description 4
239000000463 material Substances 0.000 description 4
229920000151 polyglycol Polymers 0.000 description 4
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
125000006413 ring segment Chemical group 0.000 description 4
239000004094 surface-active agent Substances 0.000 description 4
239000004546 suspension concentrate Substances 0.000 description 4
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
239000005995 Aluminium silicate Substances 0.000 description 3
244000075850 Avena orientalis Species 0.000 description 3
241000234653 Cyperus Species 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
240000007594 Oryza sativa Species 0.000 description 3
235000007164 Oryza sativa Nutrition 0.000 description 3
239000004372 Polyvinyl alcohol Substances 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
241000220261 Sinapis Species 0.000 description 3
240000006694 Stellaria media Species 0.000 description 3
241001148683 Zostera marina Species 0.000 description 3
239000004480 active ingredient Substances 0.000 description 3
125000003545 alkoxy group Chemical group 0.000 description 3
235000012211 aluminium silicate Nutrition 0.000 description 3
239000000010 aprotic solvent Substances 0.000 description 3
125000003118 aryl group Chemical group 0.000 description 3
238000009835 boiling Methods 0.000 description 3
229910052794 bromium Inorganic materials 0.000 description 3
239000000969 carrier Substances 0.000 description 3
239000000084 colloidal system Substances 0.000 description 3
235000014113 dietary fatty acids Nutrition 0.000 description 3
239000006185 dispersion Substances 0.000 description 3
238000005516 engineering process Methods 0.000 description 3
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
239000000194 fatty acid Substances 0.000 description 3
229930195729 fatty acid Natural products 0.000 description 3
150000002191 fatty alcohols Chemical class 0.000 description 3
239000003337 fertilizer Substances 0.000 description 3
125000004438 haloalkoxy group Chemical group 0.000 description 3
125000001072 heteroaryl group Chemical group 0.000 description 3
239000012442 inert solvent Substances 0.000 description 3
NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 3
238000001819 mass spectrum Methods 0.000 description 3
229910052757 nitrogen Inorganic materials 0.000 description 3
239000003960 organic solvent Substances 0.000 description 3
229910052760 oxygen Inorganic materials 0.000 description 3
MESPVSMSORHLAX-UHFFFAOYSA-N phenyl n-(4,6-dimethoxypyrimidin-2-yl)carbamate Chemical compound COC1=CC(OC)=NC(NC(=O)OC=2C=CC=CC=2)=N1 MESPVSMSORHLAX-UHFFFAOYSA-N 0.000 description 3
229920002451 polyvinyl alcohol Polymers 0.000 description 3
235000009566 rice Nutrition 0.000 description 3
239000007787 solid Substances 0.000 description 3
OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 2
MDBGGTQNNUOQRC-UHFFFAOYSA-N Allidochlor Chemical compound ClCC(=O)N(CC=C)CC=C MDBGGTQNNUOQRC-UHFFFAOYSA-N 0.000 description 2
235000007319 Avena orientalis Nutrition 0.000 description 2
241000219310 Beta vulgaris subsp. vulgaris Species 0.000 description 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
244000144786 Chrysanthemum segetum Species 0.000 description 2
235000005470 Chrysanthemum segetum Nutrition 0.000 description 2
WMLPCIHUFDKWJU-UHFFFAOYSA-N Cinosulfuron Chemical compound COCCOC1=CC=CC=C1S(=O)(=O)NC(=O)NC1=NC(OC)=NC(OC)=N1 WMLPCIHUFDKWJU-UHFFFAOYSA-N 0.000 description 2
229920000742 Cotton Polymers 0.000 description 2
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical class C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
FDNBWBAHQKZDSN-UHFFFAOYSA-N F5231 Chemical compound C1=C(Cl)C(NS(=O)(=O)CC)=CC(N2C(N(CCCF)N=N2)=O)=C1F FDNBWBAHQKZDSN-UHFFFAOYSA-N 0.000 description 2
239000005514 Flazasulfuron Chemical class 0.000 description 2
HWATZEJQIXKWQS-UHFFFAOYSA-N Flazasulfuron Chemical class COC1=CC(OC)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CN=2)C(F)(F)F)=N1 HWATZEJQIXKWQS-UHFFFAOYSA-N 0.000 description 2
RXCPQSJAVKGONC-UHFFFAOYSA-N Flumetsulam Chemical compound N1=C2N=C(C)C=CN2N=C1S(=O)(=O)NC1=C(F)C=CC=C1F RXCPQSJAVKGONC-UHFFFAOYSA-N 0.000 description 2
244000068988 Glycine max Species 0.000 description 2
235000010469 Glycine max Nutrition 0.000 description 2
244000299507 Gossypium hirsutum Species 0.000 description 2
240000005979 Hordeum vulgare Species 0.000 description 2
235000007340 Hordeum vulgare Nutrition 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
244000100545 Lolium multiflorum Species 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
239000005594 Phenmedipham Substances 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
244000082988 Secale cereale Species 0.000 description 2
235000007238 Secale cereale Nutrition 0.000 description 2
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
244000062793 Sorghum vulgare Species 0.000 description 2
235000021536 Sugar beet Nutrition 0.000 description 2
PNRAZZZISDRWMV-UHFFFAOYSA-N Terbucarb Chemical compound CNC(=O)OC1=C(C(C)(C)C)C=C(C)C=C1C(C)(C)C PNRAZZZISDRWMV-UHFFFAOYSA-N 0.000 description 2
235000021307 Triticum Nutrition 0.000 description 2
244000098338 Triticum aestivum Species 0.000 description 2
240000008042 Zea mays Species 0.000 description 2
235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 description 2
235000002017 Zea mays subsp mays Nutrition 0.000 description 2
125000004453 alkoxycarbonyl group Chemical group 0.000 description 2
125000004448 alkyl carbonyl group Chemical group 0.000 description 2
125000004390 alkyl sulfonyl group Chemical group 0.000 description 2
125000004414 alkyl thio group Chemical group 0.000 description 2
150000001412 amines Chemical class 0.000 description 2
125000003277 amino group Chemical group 0.000 description 2
239000011324 bead Substances 0.000 description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
239000011575 calcium Substances 0.000 description 2
229910052791 calcium Inorganic materials 0.000 description 2
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
WYKYKTKDBLFHCY-UHFFFAOYSA-N chloridazon Chemical compound O=C1C(Cl)=C(N)C=NN1C1=CC=CC=C1 WYKYKTKDBLFHCY-UHFFFAOYSA-N 0.000 description 2
KIEDNEWSYUYDSN-UHFFFAOYSA-N clomazone Chemical compound O=C1C(C)(C)CON1CC1=CC=CC=C1Cl KIEDNEWSYUYDSN-UHFFFAOYSA-N 0.000 description 2
MZZBPDKVEFVLFF-UHFFFAOYSA-N cyanazine Chemical compound CCNC1=NC(Cl)=NC(NC(C)(C)C#N)=N1 MZZBPDKVEFVLFF-UHFFFAOYSA-N 0.000 description 2
125000004093 cyano group Chemical group *C#N 0.000 description 2
125000000753 cycloalkyl group Chemical group 0.000 description 2
239000002270 dispersing agent Substances 0.000 description 2
239000000428 dust Substances 0.000 description 2
150000002170 ethers Chemical class 0.000 description 2
239000000945 filler Substances 0.000 description 2
125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 2
125000000262 haloalkenyl group Chemical group 0.000 description 2
150000002430 hydrocarbons Chemical group 0.000 description 2
239000002917 insecticide Substances 0.000 description 2
229910052740 iodine Inorganic materials 0.000 description 2
239000002563 ionic surfactant Substances 0.000 description 2
235000009973 maize Nutrition 0.000 description 2
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
150000004702 methyl esters Chemical class 0.000 description 2
239000002480 mineral oil Substances 0.000 description 2
239000002736 nonionic surfactant Substances 0.000 description 2
150000007524 organic acids Chemical class 0.000 description 2
125000004043 oxo group Chemical group O=* 0.000 description 2
IDOWTHOLJBTAFI-UHFFFAOYSA-N phenmedipham Chemical compound COC(=O)NC1=CC=CC(OC(=O)NC=2C=C(C)C=CC=2)=C1 IDOWTHOLJBTAFI-UHFFFAOYSA-N 0.000 description 2
229920003023 plastic Polymers 0.000 description 2
239000004033 plastic Substances 0.000 description 2
229910000027 potassium carbonate Inorganic materials 0.000 description 2
GKKCIDNWFBPDBW-UHFFFAOYSA-M potassium cyanate Chemical compound [K]OC#N GKKCIDNWFBPDBW-UHFFFAOYSA-M 0.000 description 2
229920006395 saturated elastomer Polymers 0.000 description 2
HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 2
238000009331 sowing Methods 0.000 description 2
241000894007 species Species 0.000 description 2
239000007921 spray Substances 0.000 description 2
238000001694 spray drying Methods 0.000 description 2
238000005507 spraying Methods 0.000 description 2
125000001424 substituent group Chemical group 0.000 description 2
239000000725 suspension Substances 0.000 description 2
239000000454 talc Substances 0.000 description 2
229910052623 talc Inorganic materials 0.000 description 2
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
230000009105 vegetative growth Effects 0.000 description 2
239000000080 wetting agent Substances 0.000 description 2
GXEKYRXVRROBEV-FBXFSONDSA-N (1r,2s,3r,4s)-7-oxabicyclo[2.2.1]heptane-2,3-dicarboxylic acid Chemical compound C1C[C@@H]2[C@@H](C(O)=O)[C@@H](C(=O)O)[C@H]1O2 GXEKYRXVRROBEV-FBXFSONDSA-N 0.000 description 1
HTBQOINACZOEPC-UHFFFAOYSA-N (2,4-dichlorophenyl)-(1-methyl-5-phenylmethoxypyrazol-4-yl)methanone Chemical compound C=1C=CC=CC=1COC=1N(C)N=CC=1C(=O)C1=CC=C(Cl)C=C1Cl HTBQOINACZOEPC-UHFFFAOYSA-N 0.000 description 1
IPPAUTOBDWNELX-UHFFFAOYSA-N (2-ethoxy-2-oxoethyl) 5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzoate Chemical group C1=C([N+]([O-])=O)C(C(=O)OCC(=O)OCC)=CC(OC=2C(=CC(=CC=2)C(F)(F)F)Cl)=C1 IPPAUTOBDWNELX-UHFFFAOYSA-N 0.000 description 1
JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical class OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 description 1
MGAXYKDBRBNWKT-UHFFFAOYSA-N (5-oxooxolan-2-yl)methyl 4-methylbenzenesulfonate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)OCC1OC(=O)CC1 MGAXYKDBRBNWKT-UHFFFAOYSA-N 0.000 description 1
125000004455 (C1-C3) alkylthio group Chemical group 0.000 description 1
125000006677 (C1-C3) haloalkoxy group Chemical group 0.000 description 1
XUHGTGGPZFJRMF-UHFFFAOYSA-N 1,3-dihydropyrazole-2-carboxylic acid Chemical compound OC(=O)N1CC=CN1 XUHGTGGPZFJRMF-UHFFFAOYSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
XUJLWPFSUCHPQL-UHFFFAOYSA-N 11-methyldodecan-1-ol Chemical compound CC(C)CCCCCCCCCCO XUJLWPFSUCHPQL-UHFFFAOYSA-N 0.000 description 1
YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 1
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BBKDWPHJZANJGB-IKJXHCRLSA-N quizalofop-P-tefuryl Chemical group O=C([C@H](OC=1C=CC(OC=2N=C3C=CC(Cl)=CC3=NC=2)=CC=1)C)OCC1CCCO1 BBKDWPHJZANJGB-IKJXHCRLSA-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
230000002829 reductive effect Effects 0.000 description 1
238000011160 research Methods 0.000 description 1
239000004576 sand Substances 0.000 description 1
229930195734 saturated hydrocarbon Natural products 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
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
CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
ZVCDLGYNFYZZOK-UHFFFAOYSA-M sodium cyanate Chemical compound [Na]OC#N ZVCDLGYNFYZZOK-UHFFFAOYSA-M 0.000 description 1
235000019333 sodium laurylsulphate Nutrition 0.000 description 1
229920005552 sodium lignosulfonate Polymers 0.000 description 1
NNMHYFLPFNGQFZ-UHFFFAOYSA-M sodium polyacrylate Chemical compound [Na+].[O-]C(=O)C=C NNMHYFLPFNGQFZ-UHFFFAOYSA-M 0.000 description 1
KZOJQMWTKJDSQJ-UHFFFAOYSA-M sodium;2,3-dibutylnaphthalene-1-sulfonate Chemical compound [Na+].C1=CC=C2C(S([O-])(=O)=O)=C(CCCC)C(CCCC)=CC2=C1 KZOJQMWTKJDSQJ-UHFFFAOYSA-M 0.000 description 1
239000004550 soluble concentrate Substances 0.000 description 1
238000001179 sorption measurement Methods 0.000 description 1
239000007858 starting material Substances 0.000 description 1
230000003068 static effect Effects 0.000 description 1
230000000707 stereoselective effect Effects 0.000 description 1
230000036435 stunted growth Effects 0.000 description 1
125000000547 substituted alkyl group Chemical group 0.000 description 1
150000003455 sulfinic acids Chemical class 0.000 description 1
ZDXMLEQEMNLCQG-UHFFFAOYSA-N sulfometuron methyl Chemical group COC(=O)C1=CC=CC=C1S(=O)(=O)NC(=O)NC1=NC(C)=CC(C)=N1 ZDXMLEQEMNLCQG-UHFFFAOYSA-N 0.000 description 1
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
230000002459 sustained effect Effects 0.000 description 1
RJKCKKDSSSRYCB-UHFFFAOYSA-N tebutam Chemical compound CC(C)(C)C(=O)N(C(C)C)CC1=CC=CC=C1 RJKCKKDSSSRYCB-UHFFFAOYSA-N 0.000 description 1
BCQMBFHBDZVHKU-UHFFFAOYSA-N terbumeton Chemical compound CCNC1=NC(NC(C)(C)C)=NC(OC)=N1 BCQMBFHBDZVHKU-UHFFFAOYSA-N 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
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 description 1
125000000335 thiazolyl group Chemical group 0.000 description 1
125000001544 thienyl group Chemical group 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
150000003566 thiocarboxylic acids Chemical class 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
238000013519 translation Methods 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
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
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
150000003672 ureas Chemical class 0.000 description 1
230000000007 visual effect Effects 0.000 description 1
239000001993 wax Substances 0.000 description 1
238000001238 wet grinding Methods 0.000 description 1
239000004563 wettable powder Substances 0.000 description 1
239000002023 wood Substances 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

Life Sciences & Earth Sciences (AREA)
Organic Chemistry (AREA)
Chemical & Material 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)
Agricultural Chemicals And Associated Chemicals (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Plural Heterocyclic Compounds (AREA)

CA002191759A 1994-06-01 1995-05-17 Formylaminophenylsulfonylurees, leur procede de fabrication et leur utilisation en tant qu'herbicides et regulateurs de croissance des vegetaux Expired - Lifetime CA2191759C (fr)

Applications Claiming Priority (5)

Application Number	Priority Date	Filing Date	Title
DEP4419259.2		1994-06-01
DE4419259A DE4419259A1 (de)	1994-06-01	1994-06-01	Phenylsulfonylharnstoffe mit Stickstoffsubstituenten; Verfahren zu deren Herstellung und Verwendung als Herbizide und Pflanzenwachstumsregulatoren
DE1995110078 DE19510078A1 (de)	1995-03-20	1995-03-20	Formylaminophenylsulfonylharnstoffe, Verfahren zur Herstellung und Verwendung als Herbizide und Pflanzenwachstumsregulatoren
DE19510078.6		1995-03-20
PCT/EP1995/001867 WO1995032950A1 (fr)	1994-06-01	1995-05-17	Formylaminophenylsulfonylurees, leur procede de fabrication et leur utilisation en tant qu'herbicides et regulateurs de croissance des vegetaux

Publications (2)

Publication Number	Publication Date
CA2191759A1 CA2191759A1 (fr)	1995-12-07
CA2191759C true CA2191759C (fr)	2006-10-31

Family

ID=37395778

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA002191759A Expired - Lifetime CA2191759C (fr)	1994-06-01	1995-05-17	Formylaminophenylsulfonylurees, leur procede de fabrication et leur utilisation en tant qu'herbicides et regulateurs de croissance des vegetaux

Country Status (1)

Country	Link
CA (1)	CA2191759C (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CN115433080A (zh) *	2022-10-14	2022-12-06	天津市新天进科技开发有限公司	一种用于丙烯酸精制过程的节能工艺方法和装置

1995
- 1995-05-17 CA CA002191759A patent/CA2191759C/fr not_active Expired - Lifetime

Also Published As

Publication number	Publication date
CA2191759A1 (fr)	1995-12-07

Legal Events

Date	Code	Title	Description
2002-04-24	EEER	Examination request
2015-07-21	MKEX	Expiry	Effective date: 20150519

Publication	Publication Date	Title
CA2189044C (fr)	2009-02-10	Aminophenylsulfonylurees acetylees, procedes pour leur preparation et leur utilisation comme herbicides et regulateurs de la croissance vegetale
CA2174127C (fr)	2005-12-20	Urees de phenylsulfonyle, leur procede de preparation et leur utilisation comme herbicides et comme regulateurs de la croissance vegetale
US5658854A (en)	1997-08-19	Acylated aminophenylsulfonylureas; preparation and use as herbicides and plant growth regulators
EP0666852B1 (fr)	1997-01-22	Nouvelles phenylsulfonylurees, leur preparation et leur utilisation comme herbicides et comme regulateurs de croissance vegetale
CA2144769A1 (fr)	1994-03-31	Hydroxyaminophenylsulfonylurees; leur synthese et leur utilisation comme herbicides et comme regulateurs de la croissance des plantes
US5696053A (en)	1997-12-09	Nitrogen-substituted phenylsulfonylureas; processes for their preparation, and their use as herbicides and plant growth regulators
US6316388B1 (en)	2001-11-13	N-heteroaryl-N′-(pyrid-2-yl-sulfonyl) ureas, processes for their preparation, and their use as herbicides and plant growth regulators
US5747421A (en)	1998-05-05	Formylaminophenylsulfonylureas, preparation processes and use as herbicides and plant growth regulators
US5446013A (en)	1995-08-29	2-alkyl-or-aryl-substituted-2-(pyrimidinyl-or-traizinyl-oxy(or-thio))-acotic acid derivatives, process for preparation, and use as herbicides or plant-growth regulators
CA2151498A1 (fr)	1994-06-23	Benzoylcyclohexenones; methode de preparation et utilisation comme herbicides et regulateurs de la croissance des plantes
US5847146A (en)	1998-12-08	N-heteroartyl-n'-(pyrid-2yl-sulfonyl) ureas, processes for their preparation, and their use as herbicides and plant growth regulators
US5723409A (en)	1998-03-03	Intermediates for the preparation of phenylsulfonylurea herbicides and plant growth regulators
CA2191759C (fr)	2006-10-31	Formylaminophenylsulfonylurees, leur procede de fabrication et leur utilisation en tant qu'herbicides et regulateurs de croissance des vegetaux
US5714436A (en)	1998-02-03	N-heteroaryl-N'-(pyrid-2-ylsulfonyl)ureas, processes for their preparation, and their use as herbicides and plant growth regulators
CA2206238C (fr)	2009-01-27	Sulfonylurees d'alkylidenehydrazinophenyle, methodes de preparation connexes et utilisation desdits composes comme herbicides et regulateurs de croissance des plantes
US5663118A (en)	1997-09-02	Fluoromethylsulfonyl-substituted pyridylsulfonylureas as herbicides, process for their preparation, and their use
US5861357A (en)	1999-01-19	5-acylamino-2-alkoxycarbonylphenylsulfonylureas as selective herbicides
WO1995006039A1 (fr)	1995-03-02	Nouveaux derives d'acide phenylglyoxylique, leurs procedes de preparation et leur utilisation comme herbicides et comme regulateurs de croissance vegetale
DE4311787A1 (de)	1994-11-03	Fluormethylsulfonyl-substituierte Pyridylsulfonylharnstoffe als Herbizide, Verfahren zu ihrer Herstellung und ihre Verwendung
DE19510078A1 (de)	1996-09-26	Formylaminophenylsulfonylharnstoffe, Verfahren zur Herstellung und Verwendung als Herbizide und Pflanzenwachstumsregulatoren
DE4330893A1 (de)	1995-03-16	N-Heteroaryl-N'(pyrid-2-yl-sulfonyl)-harnstoffe, Verfahren zu ihrer Herstellung und ihre Verwendung als Herbizide und Pflanzenwachstumsregulatoren
DE4335587A1 (de)	1995-05-04	N-Heteroaryl-N'-(pyrid-2-yl-sulfonyl)-Harn- stoffe, Verfahren zu ihrer Herstellung und ihre Verwendung als Herbizide und Pflanzenwachstumsregulatoren