DD263692A5 - Herbizide mittel - Google Patents

Herbizide mittel Download PDF

Info

Publication number: DD263692A5
Authority: DD; German Democratic Republic
Prior art keywords: och; chf; formula; alkyl; sch
Prior art date: 1986-06-26

Application number

DD87304130A

Other languages

German (de)

English (en)

Inventor

Theodor Pfister

Christa Fest

Klaus-Helmut Mueller

Hans-Joachim Riebel

Hans-Joachim Santel

Robert R Schmidt

Original Assignee

��@��k��

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.)

1986-06-26

Filing date

1987-06-24

Publication date

1989-01-11

1987-06-24 Application filed by ��@��k�� filed Critical ��@��k��

1989-01-11 Publication of DD263692A5 publication Critical patent/DD263692A5/de

Links

239000004009 herbicide Substances 0.000 title claims abstract description 9
230000002363 herbicidal effect Effects 0.000 title description 5
238000002360 preparation method Methods 0.000 claims abstract description 15
235000013877 carbamide Nutrition 0.000 claims abstract description 8
150000003672 ureas Chemical class 0.000 claims abstract description 7
239000000460 chlorine Chemical group 0.000 claims description 160
150000001875 compounds Chemical class 0.000 claims description 61
238000000034 method Methods 0.000 claims description 52
-1 nitro, cyano, methyl Chemical group 0.000 claims description 29
241000196324 Embryophyta Species 0.000 claims description 20
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 18
125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 16
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 16
239000000203 mixture Substances 0.000 claims description 15
239000011737 fluorine Substances 0.000 claims description 13
229910052731 fluorine Inorganic materials 0.000 claims description 13
229910052757 nitrogen Inorganic materials 0.000 claims description 13
229910052801 chlorine Chemical group 0.000 claims description 12
239000001257 hydrogen Substances 0.000 claims description 12
229910052739 hydrogen Inorganic materials 0.000 claims description 12
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 11
125000004093 cyano group Chemical group *C#N 0.000 claims description 10
150000003839 salts Chemical class 0.000 claims description 10
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 9
125000000217 alkyl group Chemical group 0.000 claims description 9
229910052736 halogen Inorganic materials 0.000 claims description 8
150000002367 halogens Chemical group 0.000 claims description 8
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 8
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 7
239000004480 active ingredient Substances 0.000 claims description 7
239000013543 active substance Substances 0.000 claims description 7
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 7
229910052794 bromium Inorganic materials 0.000 claims description 7
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 6
229910052717 sulfur Inorganic materials 0.000 claims description 6
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 5
125000004414 alkyl thio group Chemical group 0.000 claims description 5
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
125000001188 haloalkyl group Chemical group 0.000 claims description 5
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
229910052751 metal Inorganic materials 0.000 claims description 5
239000002184 metal Substances 0.000 claims description 5
239000001301 oxygen Substances 0.000 claims description 5
229910052760 oxygen Inorganic materials 0.000 claims description 5
239000011593 sulfur Substances 0.000 claims description 5
239000004606 Fillers/Extenders Substances 0.000 claims description 4
125000003545 alkoxy group Chemical group 0.000 claims description 4
125000003282 alkyl amino group Chemical group 0.000 claims description 4
125000001153 fluoro group Chemical group F* 0.000 claims description 4
125000004438 haloalkoxy group Chemical group 0.000 claims description 4
150000002897 organic nitrogen compounds Chemical class 0.000 claims description 4
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 claims description 3
150000002739 metals Chemical class 0.000 claims description 3
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 2
125000003342 alkenyl group Chemical group 0.000 claims description 2
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
125000004448 alkyl carbonyl group Chemical group 0.000 claims description 2
125000000304 alkynyl group Chemical group 0.000 claims description 2
125000003710 aryl alkyl group Chemical group 0.000 claims description 2
125000004663 dialkyl amino group Chemical group 0.000 claims description 2
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 2
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 2
239000004094 surface-active agent Substances 0.000 claims description 2
150000002431 hydrogen Chemical class 0.000 claims 6
230000008635 plant growth Effects 0.000 claims 2
GJKVOBOIRKNMPZ-UHFFFAOYSA-N CCOC(N(NOC)SCC)(OC(F)F)SC Chemical class CCOC(N(NOC)SCC)(OC(F)F)SC GJKVOBOIRKNMPZ-UHFFFAOYSA-N 0.000 claims 1
HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 claims 1
125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims 1
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
239000007858 starting material Substances 0.000 description 12
238000006243 chemical reaction Methods 0.000 description 11
239000003085 diluting agent Substances 0.000 description 10
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
239000002904 solvent Substances 0.000 description 9
ZWEHNKRNPOVVGH-UHFFFAOYSA-N Methyl ethyl ketone Natural products CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 8
239000002253 acid Substances 0.000 description 8
150000003254 radicals Chemical class 0.000 description 8
239000000126 substance Substances 0.000 description 8
125000001424 substituent group Chemical group 0.000 description 8
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
238000009472 formulation Methods 0.000 description 7
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 6
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
239000000370 acceptor Substances 0.000 description 6
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 6
239000003995 emulsifying agent Substances 0.000 description 6
125000004435 hydrogen atom Chemical group [H]* 0.000 description 6
238000002844 melting Methods 0.000 description 6
230000008018 melting Effects 0.000 description 6
239000003960 organic solvent Substances 0.000 description 6
159000000000 sodium salts Chemical class 0.000 description 6
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 5
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 5
230000006378 damage Effects 0.000 description 5
239000008187 granular material Substances 0.000 description 5
125000005241 heteroarylamino group Chemical group 0.000 description 5
239000011734 sodium Substances 0.000 description 5
239000000243 solution Substances 0.000 description 5
NFDXQGNDWIPXQL-UHFFFAOYSA-N 1-cyclooctyldiazocane Chemical compound C1CCCCCCC1N1NCCCCCC1 NFDXQGNDWIPXQL-UHFFFAOYSA-N 0.000 description 4
HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 4
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 4
WADSJYLPJPTMLN-UHFFFAOYSA-N 3-(cycloundecen-1-yl)-1,2-diazacycloundec-2-ene Chemical compound C1CCCCCCCCC=C1C1=NNCCCCCCCC1 WADSJYLPJPTMLN-UHFFFAOYSA-N 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
150000001408 amides Chemical class 0.000 description 4
239000012973 diazabicyclooctane Substances 0.000 description 4
230000000694 effects Effects 0.000 description 4
RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
150000002170 ethers Chemical class 0.000 description 4
229910052500 inorganic mineral Inorganic materials 0.000 description 4
SYBYTAAJFKOIEJ-UHFFFAOYSA-N methyl iso-propyl ketone Natural products CC(C)C(C)=O SYBYTAAJFKOIEJ-UHFFFAOYSA-N 0.000 description 4
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
239000000843 powder Substances 0.000 description 4
229910052708 sodium Inorganic materials 0.000 description 4
239000002689 soil Substances 0.000 description 4
238000010626 work up procedure Methods 0.000 description 4
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
241000208296 Datura Species 0.000 description 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
240000006694 Stellaria media Species 0.000 description 3
235000021307 Triticum Nutrition 0.000 description 3
244000098338 Triticum aestivum Species 0.000 description 3
125000002877 alkyl aryl group Chemical group 0.000 description 3
239000004202 carbamide Substances 0.000 description 3
239000003054 catalyst Substances 0.000 description 3
239000012141 concentrate Substances 0.000 description 3
XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 3
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
150000002576 ketones Chemical class 0.000 description 3
238000004519 manufacturing process Methods 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
230000000269 nucleophilic effect Effects 0.000 description 3
229920000151 polyglycol Polymers 0.000 description 3
239000010695 polyglycol Substances 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
239000011435 rock Substances 0.000 description 3
VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 2
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 2
NTSLROIKFLNUIJ-UHFFFAOYSA-N 5-Ethyl-2-methylpyridine Chemical compound CCC1=CC=C(C)N=C1 NTSLROIKFLNUIJ-UHFFFAOYSA-N 0.000 description 2
235000005781 Avena Nutrition 0.000 description 2
244000075850 Avena orientalis Species 0.000 description 2
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
244000192528 Chrysanthemum parthenium Species 0.000 description 2
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 2
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
235000021506 Ipomoea Nutrition 0.000 description 2
241000207783 Ipomoea Species 0.000 description 2
241000209082 Lolium Species 0.000 description 2
235000017945 Matricaria Nutrition 0.000 description 2
235000007232 Matricaria chamomilla Nutrition 0.000 description 2
NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 2
UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 2
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
241000209094 Oryza Species 0.000 description 2
241000209117 Panicum Species 0.000 description 2
235000006443 Panicum miliaceum subsp. miliaceum Nutrition 0.000 description 2
235000009037 Panicum miliaceum subsp. ruderale Nutrition 0.000 description 2
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
235000002634 Solanum Nutrition 0.000 description 2
241000207763 Solanum Species 0.000 description 2
235000011684 Sorghum saccharatum Nutrition 0.000 description 2
244000062793 Sorghum vulgare Species 0.000 description 2
240000008042 Zea mays Species 0.000 description 2
235000002017 Zea mays subsp mays Nutrition 0.000 description 2
150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
125000003118 aryl group Chemical group 0.000 description 2
239000011230 binding agent Substances 0.000 description 2
239000011575 calcium Substances 0.000 description 2
229910052791 calcium Inorganic materials 0.000 description 2
AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 2
239000000920 calcium hydroxide Substances 0.000 description 2
229910001861 calcium hydroxide Inorganic materials 0.000 description 2
239000000969 carrier Substances 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
238000007796 conventional method Methods 0.000 description 2
WQJONRMBVKFKOB-UHFFFAOYSA-N cyanatosulfanyl cyanate Chemical class N#COSOC#N WQJONRMBVKFKOB-UHFFFAOYSA-N 0.000 description 2
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
239000002837 defoliant Substances 0.000 description 2
210000003298 dental enamel Anatomy 0.000 description 2
239000002274 desiccant Substances 0.000 description 2
JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 2
125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
229940113088 dimethylacetamide Drugs 0.000 description 2
XXBDWLFCJWSEKW-UHFFFAOYSA-N dimethylbenzylamine Chemical compound CN(C)CC1=CC=CC=C1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 0.000 description 2
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
239000002270 dispersing agent Substances 0.000 description 2
239000000975 dye Substances 0.000 description 2
235000013399 edible fruits Nutrition 0.000 description 2
239000000839 emulsion Substances 0.000 description 2
150000002148 esters Chemical class 0.000 description 2
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 2
238000002955 isolation Methods 0.000 description 2
239000007788 liquid Substances 0.000 description 2
239000011707 mineral Substances 0.000 description 2
239000002480 mineral oil Substances 0.000 description 2
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
150000002825 nitriles Chemical class 0.000 description 2
235000015097 nutrients Nutrition 0.000 description 2
TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 2
239000012074 organic phase Substances 0.000 description 2
239000006072 paste Substances 0.000 description 2
239000003208 petroleum Substances 0.000 description 2
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 2
229910000027 potassium carbonate Inorganic materials 0.000 description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
239000007787 solid Substances 0.000 description 2
238000005507 spraying Methods 0.000 description 2
239000000725 suspension Substances 0.000 description 2
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 2
235000015112 vegetable and seed oil Nutrition 0.000 description 2
239000008158 vegetable oil Substances 0.000 description 2
239000008096 xylene Substances 0.000 description 2
HEJVROKEIMJTIN-UHFFFAOYSA-N (2-butan-2-yl-4,6-dinitrophenyl) (2,4-dinitrophenyl) carbonate Chemical compound CCC(C)C1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1OC(=O)OC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O HEJVROKEIMJTIN-UHFFFAOYSA-N 0.000 description 1
125000004893 1,1-dimethylethylamino group Chemical group CC(C)(C)N* 0.000 description 1
FIDRAVVQGKNYQK-UHFFFAOYSA-N 1,2,3,4-tetrahydrotriazine Chemical compound C1NNNC=C1 FIDRAVVQGKNYQK-UHFFFAOYSA-N 0.000 description 1
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
ZOXIHWOGXJYBOS-UHFFFAOYSA-N 1-(4,6-dimethoxy-1,3,5-triazin-2-yl)-3-[2-(trifluoromethoxy)phenyl]sulfonylurea Chemical compound COC1=NC(OC)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)OC(F)(F)F)=N1 ZOXIHWOGXJYBOS-UHFFFAOYSA-N 0.000 description 1
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IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
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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)
Environmental Sciences (AREA)
Agronomy & Crop Science (AREA)
Engineering & Computer Science (AREA)
Dentistry (AREA)
General Health & Medical Sciences (AREA)
Wood Science & Technology (AREA)
Zoology (AREA)
Plant Pathology (AREA)
Pest Control & Pesticides (AREA)
Health & Medical Sciences (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Plural Heterocyclic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Thiazole And Isothizaole Compounds (AREA)

DD87304130A 1986-06-26 1987-06-24 Herbizide mittel DD263692A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE19863621320 DE3621320A1 (de)	1986-06-26	1986-06-26	3-substituierte 1-(2-halogenalkoxy-benzolsulfonyl)-3-heteroaryl-(thio)harnstoffe

Publications (1)

Publication Number	Publication Date
DD263692A5 true DD263692A5 (de)	1989-01-11

Family

ID=6303693

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD87304130A DD263692A5 (de)	1986-06-26	1987-06-24	Herbizide mittel

Country Status (13)

Country	Link
EP (1)	EP0251079B1 (da)
JP (1)	JPS6314775A (da)
AT (1)	ATE89555T1 (da)
AU (1)	AU610067B2 (da)
BR (1)	BR8703202A (da)
CA (1)	CA1292230C (da)
DD (1)	DD263692A5 (da)
DE (2)	DE3621320A1 (da)
DK (1)	DK164598C (da)
ES (1)	ES2054631T3 (da)
HU (1)	HU200754B (da)
IL (1)	IL82963A0 (da)
ZA (1)	ZA874596B (da)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5328896A (en) *	1989-12-19	1994-07-12	Bayer Aktiengesellschaft	Preparing herbicidal sulphonylurea salts
DE4018349A1 (de) *	1989-12-19	1991-06-20	Bayer Ag	Verfahren zur herstellung von sulfonylharnstoff-salzen, neue sulfonylharnstoff-salze und ihre verwendung als herbizide

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4452628A (en) *	1979-07-26	1984-06-05	E. I. Du Pont De Nemours And Company	Herbicidal sulfonamides
US4371391A (en) *	1980-09-15	1983-02-01	E. I. Du Pont De Nemours And Company	Herbicidal sulfonamides
DE3234448A1 (de) *	1982-09-17	1984-03-22	Hoechst Ag, 6230 Frankfurt	Neue pyrimidinylharnstoffe, verfahren zu ihrer herstellung, sie enthaltende mittel und deren verwendung als herbizide
US4515626A (en) *	1982-10-06	1985-05-07	Ciba Geigy Corporation	N-(Cyclopropyl-triazinyl-n'-(arylsulfonyl) ureas having herbicidal activity
DE3322280A1 (de) *	1983-06-16	1985-01-03	Schering AG, 1000 Berlin und 4709 Bergkamen	Substituierte sulfonylharnstoffe, verfahren zur herstellung dieser verbindungen sowie diese enthaltende mittel mit herbizider und pflanzenwuchsregulierender wirkung
US4685961A (en) *	1984-02-14	1987-08-11	Ciba-Geigy Corporation	Herbicidal sulfonylureas
US4689069A (en) *	1984-08-08	1987-08-25	E. I. Du Pont De Nemours And Company	Herbicidal acetylenic pyrimidines and triazines
DE3431917A1 (de) *	1984-08-30	1986-03-13	Bayer Ag, 5090 Leverkusen	1-(2-trifluormethoxy-phenylsulfonyl)-3- heteroaryl-(thio)-harnstoffe

1986
- 1986-06-26 DE DE19863621320 patent/DE3621320A1/de not_active Withdrawn
1987
- 1987-06-19 AT AT87108837T patent/ATE89555T1/de not_active IP Right Cessation
- 1987-06-19 EP EP87108837A patent/EP0251079B1/de not_active Expired - Lifetime
- 1987-06-19 ES ES87108837T patent/ES2054631T3/es not_active Expired - Lifetime
- 1987-06-19 DE DE8787108837T patent/DE3785888D1/de not_active Expired - Fee Related
- 1987-06-23 AU AU74634/87A patent/AU610067B2/en not_active Ceased
- 1987-06-23 IL IL82963A patent/IL82963A0/xx not_active IP Right Cessation
- 1987-06-24 DD DD87304130A patent/DD263692A5/de not_active IP Right Cessation
- 1987-06-24 CA CA000540439A patent/CA1292230C/en not_active Expired - Lifetime
- 1987-06-25 BR BR8703202A patent/BR8703202A/pt not_active IP Right Cessation
- 1987-06-25 DK DK324987A patent/DK164598C/da not_active IP Right Cessation
- 1987-06-25 JP JP62156707A patent/JPS6314775A/ja active Pending
- 1987-06-25 ZA ZA874596A patent/ZA874596B/xx unknown
- 1987-06-26 HU HU872906A patent/HU200754B/hu not_active IP Right Cessation

Also Published As

Publication number	Publication date
HUT45028A (en)	1988-05-30
EP0251079A3 (en)	1989-10-25
DE3785888D1 (de)	1993-06-24
DK164598B (da)	1992-07-20
HU200754B (en)	1990-08-28
AU7463487A (en)	1988-01-07
EP0251079B1 (de)	1993-05-19
AU610067B2 (en)	1991-05-16
JPS6314775A (ja)	1988-01-21
DK324987D0 (da)	1987-06-25
IL82963A0 (en)	1987-12-20
DK164598C (da)	1992-12-07
ZA874596B (en)	1988-04-27
CA1292230C (en)	1991-11-19
DE3621320A1 (de)	1988-01-07
ES2054631T3 (es)	1994-08-16
DK324987A (da)	1987-12-27
ATE89555T1 (de)	1993-06-15
BR8703202A (pt)	1988-03-15
EP0251079A2 (de)	1988-01-07

Legal Events

Date	Code	Title	Description
1997-01-02	ENJ	Ceased due to non-payment of renewal fee

Publication	Publication Date	Title
EP0161602B1 (de)	1989-10-04	6-Chlorbenzazolyloxyacetamide
EP0300344B1 (de)	1993-10-06	Halogenierte Thiadiazolyl-oxyessig-säureamide, Verfahren und Zwischenprodukte zu ihrer Herstellung und ihre Verwendung als Herbizide
DE3627411A1 (de)	1988-02-18	Triazolo-pyrimidin-2-sulfonamide
EP0173312A1 (de)	1986-03-05	1-(2-Trifluormethoxy-phenylsulfonyl)-3-heteroaryl-(thio)-harnstoffe
DD263692A5 (de)	1989-01-11	Herbizide mittel
DE3413490A1 (de)	1985-10-17	2-(alkoximinoalkyloxycarbonyl)-phenylsulfonylharnstoffe
EP0173320A1 (de)	1986-03-05	Substituierte Carbonylphenylsulfonylguanidine
DE3420769A1 (de)	1985-12-05	Substituierte phenylsulfonylharnstoffe
EP0307753B1 (de)	1992-11-11	Sulfonyliso(thio)harnstoffe sowie ein Verfahren und neue Zwischenprodukte zu ihrer Herstellung
EP0023287B1 (de)	1983-02-09	Gegenmittel zum Schutz von Kulturpflanzen vor Schädigungen durch Herbizide
EP0192117A2 (de)	1986-08-27	5-Chlor-1,3,4-thiadiazol-2-yloxy-acetamide
DD238319A5 (de)	1986-08-20	Herbizide mittel
DE3642824A1 (de)	1988-06-30	Substituierte 1-benzylsulfonyl-3-heteroaryl-(thio)harnstoffe
EP0431390B1 (de)	1994-01-12	Substituierte Triazolinone
DE3808739A1 (de)	1989-09-28	Pyrimidin-derivate
DE3431926A1 (de)	1986-03-06	Amidinoazole
DE3602379A1 (de)	1987-07-30	Substituierte phenylharnstoffe
DE3413565A1 (de)	1985-10-24	Substituierte sulfonylharnstoffe
DE4022478A1 (de)	1992-01-16	Nicotinsaeurederivate
DE19501843A1 (de)	1996-06-20	Substituierte Sulfonylharnstoffe
DE3502266A1 (de)	1986-08-07	Optisch aktive phenoxypropionsaeure-derivate
DE3602679A1 (de)	1987-08-06	Acylierte sulfonylguanidine
EP0590416A1 (de)	1994-04-06	Substituierte Thienylsulfonylharnstoffe als Herbizide
DE3431933A1 (de)	1986-03-06	Heteroarylthioharnstoffe
DE3626860A1 (de)	1988-02-11	Acylierte 1-(2-oxyaminosulfonylphenylsulfonyl)-3-heteroaryl-harnstoffe