DD152899A5 - Herbizides mittel - Google Patents

Herbizides mittel Download PDF

Info

Publication number: DD152899A5
Authority: DD; German Democratic Republic
Prior art keywords: phenoxy; propionate; tolyloxy; trifluoro; halogen
Prior art date: 1979-05-23

Application number

DD80221273A

Other languages

German (de)

English (en)

Inventor

Milos Suchy

Original Assignee

Hoffmann La Roche

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.)

1979-05-23

Filing date

1980-05-21

Publication date

1981-12-16

1980-05-21 Application filed by Hoffmann La Roche filed Critical Hoffmann La Roche

1981-12-16 Publication of DD152899A5 publication Critical patent/DD152899A5/de

Links

239000004009 herbicide Substances 0.000 title claims description 13
150000001875 compounds Chemical class 0.000 claims abstract description 50
229910052736 halogen Inorganic materials 0.000 claims abstract description 27
150000002367 halogens Chemical class 0.000 claims abstract description 27
239000000203 mixture Substances 0.000 claims abstract description 26
230000002363 herbicidal effect Effects 0.000 claims abstract description 22
238000000034 method Methods 0.000 claims abstract description 15
125000000217 alkyl group Chemical group 0.000 claims abstract description 12
239000001257 hydrogen Substances 0.000 claims abstract description 12
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 12
125000003118 aryl group Chemical group 0.000 claims abstract description 11
239000012876 carrier material Substances 0.000 claims abstract description 10
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 10
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 9
125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 7
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 7
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 6
125000003545 alkoxy group Chemical group 0.000 claims abstract description 6
239000003795 chemical substances by application Substances 0.000 claims abstract description 6
238000002360 preparation method Methods 0.000 claims abstract description 6
125000001424 substituent group Chemical group 0.000 claims abstract description 6
-1 o-nitrophenacyl Chemical group 0.000 claims description 91
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 52
XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims description 35
241000196324 Embryophyta Species 0.000 claims description 15
239000002253 acid Substances 0.000 claims description 14
WROZTZHKRRNHBS-UHFFFAOYSA-N phenyl propaneperoxoate Chemical compound CCC(=O)OOC1=CC=CC=C1 WROZTZHKRRNHBS-UHFFFAOYSA-N 0.000 claims description 10
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 9
229910052801 chlorine Inorganic materials 0.000 claims description 9
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
XAKBSHICSHRJCL-UHFFFAOYSA-N [CH2]C(=O)C1=CC=CC=C1 Chemical group [CH2]C(=O)C1=CC=CC=C1 XAKBSHICSHRJCL-UHFFFAOYSA-N 0.000 claims description 6
239000000460 chlorine Substances 0.000 claims description 6
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 5
229910052783 alkali metal Inorganic materials 0.000 claims description 5
125000003710 aryl alkyl group Chemical group 0.000 claims description 5
125000001309 chloro group Chemical group Cl* 0.000 claims description 5
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
229910052794 bromium Inorganic materials 0.000 claims description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
OVSKIKFHRZPJSS-UHFFFAOYSA-N 2,4-D Chemical compound OC(=O)COC1=CC=C(Cl)C=C1Cl OVSKIKFHRZPJSS-UHFFFAOYSA-N 0.000 claims description 3
229910052799 carbon Inorganic materials 0.000 claims description 3
150000001298 alcohols Chemical class 0.000 claims description 2
150000001340 alkali metals Chemical class 0.000 claims description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
238000004519 manufacturing process Methods 0.000 claims description 2
125000005424 tosyloxy group Chemical group S(=O)(=O)(C1=CC=C(C)C=C1)O* 0.000 claims description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
229930194542 Keto Natural products 0.000 claims 1
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
125000000468 ketone group Chemical group 0.000 claims 1
239000004480 active ingredient Substances 0.000 abstract description 10
101100242909 Streptococcus pneumoniae (strain ATCC BAA-255 / R6) pbpA gene Proteins 0.000 abstract 1
101100269618 Streptococcus pneumoniae serotype 4 (strain ATCC BAA-334 / TIGR4) aliA gene Proteins 0.000 abstract 1
101100439974 Streptococcus pneumoniae serotype 4 (strain ATCC BAA-334 / TIGR4) clpE gene Proteins 0.000 abstract 1
239000000470 constituent Substances 0.000 abstract 1
101150109310 msrAB1 gene Proteins 0.000 abstract 1
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 34
235000019260 propionic acid Nutrition 0.000 description 17
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 17
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
238000006243 chemical reaction Methods 0.000 description 11
SXERGJJQSKIUIC-UHFFFAOYSA-N 2-Phenoxypropionic acid Chemical compound OC(=O)C(C)OC1=CC=CC=C1 SXERGJJQSKIUIC-UHFFFAOYSA-N 0.000 description 10
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
239000000080 wetting agent Substances 0.000 description 8
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 7
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 6
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
239000002904 solvent Substances 0.000 description 6
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
239000004202 carbamide Substances 0.000 description 5
150000004820 halides Chemical class 0.000 description 5
239000000047 product Substances 0.000 description 5
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 4
SUSRORUBZHMPCO-UHFFFAOYSA-N MC-4379 Chemical compound C1=C([N+]([O-])=O)C(C(=O)OC)=CC(OC=2C(=CC(Cl)=CC=2)Cl)=C1 SUSRORUBZHMPCO-UHFFFAOYSA-N 0.000 description 4
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 4
239000013543 active substance Substances 0.000 description 4
230000017074 necrotic cell death Effects 0.000 description 4
238000010992 reflux Methods 0.000 description 4
150000003839 salts Chemical class 0.000 description 4
239000007787 solid Substances 0.000 description 4
239000007858 starting material Substances 0.000 description 4
GZHPNIQBPGUSSX-UHFFFAOYSA-N 2-bromo-1-(3-nitrophenyl)ethanone Chemical compound [O-][N+](=O)C1=CC=CC(C(=O)CBr)=C1 GZHPNIQBPGUSSX-UHFFFAOYSA-N 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
244000062793 Sorghum vulgare Species 0.000 description 3
239000007859 condensation product Substances 0.000 description 3
230000000694 effects Effects 0.000 description 3
239000004495 emulsifiable concentrate Substances 0.000 description 3
239000003995 emulsifying agent Substances 0.000 description 3
239000003701 inert diluent Substances 0.000 description 3
239000012442 inert solvent Substances 0.000 description 3
229910052757 nitrogen Inorganic materials 0.000 description 3
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
229910052708 sodium Inorganic materials 0.000 description 3
239000011734 sodium Substances 0.000 description 3
229910000104 sodium hydride Inorganic materials 0.000 description 3
239000012312 sodium hydride Substances 0.000 description 3
229910052938 sodium sulfate Inorganic materials 0.000 description 3
235000011152 sodium sulphate Nutrition 0.000 description 3
239000007921 spray Substances 0.000 description 3
125000003107 substituted aryl group Chemical group 0.000 description 3
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
YIVXMZJTEQBPQO-UHFFFAOYSA-N 2,4-DB Chemical group OC(=O)CCCOC1=CC=C(Cl)C=C1Cl YIVXMZJTEQBPQO-UHFFFAOYSA-N 0.000 description 2
239000002794 2,4-DB Substances 0.000 description 2
YOYAIZYFCNQIRF-UHFFFAOYSA-N 2,6-dichlorobenzonitrile Chemical compound ClC1=CC=CC(Cl)=C1C#N YOYAIZYFCNQIRF-UHFFFAOYSA-N 0.000 description 2
OWZPCEFYPSAJFR-UHFFFAOYSA-N 2-(butan-2-yl)-4,6-dinitrophenol Chemical compound CCC(C)C1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1O OWZPCEFYPSAJFR-UHFFFAOYSA-N 0.000 description 2
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 2
OOLBCHYXZDXLDS-UHFFFAOYSA-N 2-[4-(2,4-dichlorophenoxy)phenoxy]propanoic acid Chemical compound C1=CC(OC(C)C(O)=O)=CC=C1OC1=CC=C(Cl)C=C1Cl OOLBCHYXZDXLDS-UHFFFAOYSA-N 0.000 description 2
BSFAVVHPEZCASB-UHFFFAOYSA-N 2-[4-(4-chlorophenoxy)phenoxy]propanoic acid Chemical compound C1=CC(OC(C)C(O)=O)=CC=C1OC1=CC=C(Cl)C=C1 BSFAVVHPEZCASB-UHFFFAOYSA-N 0.000 description 2
WZWWEVCLPKAQTA-UHFFFAOYSA-N 2-bromo-1-(2-chlorophenyl)ethanone Chemical compound ClC1=CC=CC=C1C(=O)CBr WZWWEVCLPKAQTA-UHFFFAOYSA-N 0.000 description 2
UPMXNNIRAGDFEH-UHFFFAOYSA-N 3,5-dibromo-4-hydroxybenzonitrile Chemical compound OC1=C(Br)C=C(C#N)C=C1Br UPMXNNIRAGDFEH-UHFFFAOYSA-N 0.000 description 2
239000005484 Bifenox Substances 0.000 description 2
229940126062 Compound A Drugs 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
244000058871 Echinochloa crus-galli Species 0.000 description 2
GXAMYUGOODKVRM-UHFFFAOYSA-N Flurecol Chemical compound C1=CC=C2C(C(=O)O)(O)C3=CC=CC=C3C2=C1 GXAMYUGOODKVRM-UHFFFAOYSA-N 0.000 description 2
235000010469 Glycine max Nutrition 0.000 description 2
NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 2
QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
SUZRRICLUFMAQD-UHFFFAOYSA-N N-Methyltaurine Chemical compound CNCCS(O)(=O)=O SUZRRICLUFMAQD-UHFFFAOYSA-N 0.000 description 2
240000007594 Oryza sativa Species 0.000 description 2
235000007164 Oryza sativa Nutrition 0.000 description 2
CHNUNORXWHYHNE-UHFFFAOYSA-N Oxadiazon Chemical compound C1=C(Cl)C(OC(C)C)=CC(N2C(OC(=N2)C(C)(C)C)=O)=C1Cl CHNUNORXWHYHNE-UHFFFAOYSA-N 0.000 description 2
235000011999 Panicum crusgalli Nutrition 0.000 description 2
241001355178 Setaria faberi Species 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
235000021307 Triticum Nutrition 0.000 description 2
244000098338 Triticum aestivum Species 0.000 description 2
239000000370 acceptor Substances 0.000 description 2
235000004279 alanine Nutrition 0.000 description 2
VGPYEHKOIGNJKV-UHFFFAOYSA-N asulam Chemical compound COC(=O)NS(=O)(=O)C1=CC=C(N)C=C1 VGPYEHKOIGNJKV-UHFFFAOYSA-N 0.000 description 2
MCOQHIWZJUDQIC-UHFFFAOYSA-N barban Chemical compound ClCC#CCOC(=O)NC1=CC=CC(Cl)=C1 MCOQHIWZJUDQIC-UHFFFAOYSA-N 0.000 description 2
239000002585 base Substances 0.000 description 2
HYJSGOXICXYZGS-UHFFFAOYSA-N benazolin Chemical compound C1=CC=C2SC(=O)N(CC(=O)O)C2=C1Cl HYJSGOXICXYZGS-UHFFFAOYSA-N 0.000 description 2
238000009835 boiling Methods 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
238000002425 crystallisation Methods 0.000 description 2
230000008025 crystallization Effects 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
235000014113 dietary fatty acids Nutrition 0.000 description 2
SDIXRDNYIMOKSG-UHFFFAOYSA-L disodium methyl arsenate Chemical compound [Na+].[Na+].C[As]([O-])([O-])=O SDIXRDNYIMOKSG-UHFFFAOYSA-L 0.000 description 2
150000002148 esters Chemical class 0.000 description 2
239000012259 ether extract Substances 0.000 description 2
239000000194 fatty acid Substances 0.000 description 2
229930195729 fatty acid Natural products 0.000 description 2
239000003337 fertilizer Substances 0.000 description 2
XDDAORKBJWWYJS-UHFFFAOYSA-N glyphosate Chemical compound OC(=O)CNCP(O)(O)=O XDDAORKBJWWYJS-UHFFFAOYSA-N 0.000 description 2
GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 2
239000011261 inert gas Substances 0.000 description 2
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
239000000463 material Substances 0.000 description 2
FOXFZRUHNHCZPX-UHFFFAOYSA-N metribuzin Chemical compound CSC1=NN=C(C(C)(C)C)C(=O)N1N FOXFZRUHNHCZPX-UHFFFAOYSA-N 0.000 description 2
235000019713 millet Nutrition 0.000 description 2
239000002480 mineral oil Substances 0.000 description 2
235000010446 mineral oil Nutrition 0.000 description 2
JITOKQVGRJSHHA-UHFFFAOYSA-M monosodium methyl arsenate Chemical group [Na+].C[As](O)([O-])=O JITOKQVGRJSHHA-UHFFFAOYSA-M 0.000 description 2
230000003287 optical effect Effects 0.000 description 2
150000007530 organic bases Chemical class 0.000 description 2
UNWWULGOIQWPMP-UHFFFAOYSA-N phenacyl 2-bromopropanoate Chemical compound CC(Br)C(=O)OCC(=O)C1=CC=CC=C1 UNWWULGOIQWPMP-UHFFFAOYSA-N 0.000 description 2
NQQVFXUMIDALNH-UHFFFAOYSA-N picloram Chemical compound NC1=C(Cl)C(Cl)=NC(C(O)=O)=C1Cl NQQVFXUMIDALNH-UHFFFAOYSA-N 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
LFULEKSKNZEWOE-UHFFFAOYSA-N propanil Chemical compound CCC(=O)NC1=CC=C(Cl)C(Cl)=C1 LFULEKSKNZEWOE-UHFFFAOYSA-N 0.000 description 2
150000003254 radicals Chemical class 0.000 description 2
235000009566 rice Nutrition 0.000 description 2
239000000741 silica gel Substances 0.000 description 2
229910002027 silica gel Inorganic materials 0.000 description 2
ODCWYMIRDDJXKW-UHFFFAOYSA-N simazine Chemical compound CCNC1=NC(Cl)=NC(NCC)=N1 ODCWYMIRDDJXKW-UHFFFAOYSA-N 0.000 description 2
MGLWZSOBALDPEK-UHFFFAOYSA-N simetryn Chemical compound CCNC1=NC(NCC)=NC(SC)=N1 MGLWZSOBALDPEK-UHFFFAOYSA-N 0.000 description 2
HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 2
238000001179 sorption measurement Methods 0.000 description 2
238000003756 stirring Methods 0.000 description 2
239000000725 suspension Substances 0.000 description 2
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
BSFAVVHPEZCASB-SNVBAGLBSA-N (2r)-2-[4-(4-chlorophenoxy)phenoxy]propanoic acid Chemical compound C1=CC(O[C@H](C)C(O)=O)=CC=C1OC1=CC=C(Cl)C=C1 BSFAVVHPEZCASB-SNVBAGLBSA-N 0.000 description 1
UVMTZTPUIFOAGM-UHFFFAOYSA-N (3-chlorophenyl)carbamic acid Chemical compound OC(=O)NC1=CC=CC(Cl)=C1 UVMTZTPUIFOAGM-UHFFFAOYSA-N 0.000 description 1
WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
JARFAUHJHIUGCO-UHFFFAOYSA-N 1,2-dimethyl-3,5-diphenyl-3h-pyrazole Chemical compound CN1N(C)C(C=2C=CC=CC=2)C=C1C1=CC=CC=C1 JARFAUHJHIUGCO-UHFFFAOYSA-N 0.000 description 1
OWRHJTUZVUYYNA-UHFFFAOYSA-N 1-methoxy-3-methylurea Chemical compound CNC(=O)NOC OWRHJTUZVUYYNA-UHFFFAOYSA-N 0.000 description 1
OFAPSLLQSSHRSQ-UHFFFAOYSA-N 1H-triazine-2,4-diamine Chemical compound NN1NC=CC(N)=N1 OFAPSLLQSSHRSQ-UHFFFAOYSA-N 0.000 description 1
125000001917 2,4-dinitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C(=C1*)[N+]([O-])=O)[N+]([O-])=O 0.000 description 1
WNTGYJSOUMFZEP-UHFFFAOYSA-N 2-(4-chloro-2-methylphenoxy)propanoic acid Chemical compound OC(=O)C(C)OC1=CC=C(Cl)C=C1C WNTGYJSOUMFZEP-UHFFFAOYSA-N 0.000 description 1
WZZRJCUYSKKFHO-UHFFFAOYSA-N 2-(n-benzoyl-3,4-dichloroanilino)propanoic acid Chemical compound C=1C=C(Cl)C(Cl)=CC=1N(C(C)C(O)=O)C(=O)C1=CC=CC=C1 WZZRJCUYSKKFHO-UHFFFAOYSA-N 0.000 description 1
DASJDMQCPIDJIF-UHFFFAOYSA-N 2-bromo-1-(2,4-dichlorophenyl)ethanone Chemical compound ClC1=CC=C(C(=O)CBr)C(Cl)=C1 DASJDMQCPIDJIF-UHFFFAOYSA-N 0.000 description 1
XMGAXELQRATLJP-UHFFFAOYSA-N 2-bromo-1-(2-methylphenyl)ethanone Chemical compound CC1=CC=CC=C1C(=O)CBr XMGAXELQRATLJP-UHFFFAOYSA-N 0.000 description 1
SGXUUCSRVVSMGK-UHFFFAOYSA-N 2-bromo-1-(2-nitrophenyl)ethanone Chemical compound [O-][N+](=O)C1=CC=CC=C1C(=O)CBr SGXUUCSRVVSMGK-UHFFFAOYSA-N 0.000 description 1
IOOHBIFQNQQUFI-UHFFFAOYSA-N 2-bromo-1-(3-methoxyphenyl)ethanone Chemical compound COC1=CC=CC(C(=O)CBr)=C1 IOOHBIFQNQQUFI-UHFFFAOYSA-N 0.000 description 1
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239000004563 wettable powder Substances 0.000 description 1

Classifications

- 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
- A01N39/00—Biocides, pest repellants or attractants, or plant growth regulators containing aryloxy- or arylthio-aliphatic or cycloaliphatic compounds, containing the group or, e.g. phenoxyethylamine, phenylthio-acetonitrile, phenoxyacetone
- A01N39/02—Aryloxy-carboxylic acids; Derivatives thereof

Landscapes

Life Sciences & Earth Sciences (AREA)
Dentistry (AREA)
Pest Control & Pesticides (AREA)
Plant Pathology (AREA)
Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Agronomy & Crop Science (AREA)
General Health & Medical Sciences (AREA)
Wood Science & Technology (AREA)
Zoology (AREA)
Environmental Sciences (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

DD80221273A 1979-05-23 1980-05-21 Herbizides mittel DD152899A5 (de)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
CH483879		1979-05-23
CH233080		1980-03-25

Publications (1)

Publication Number	Publication Date
DD152899A5 true DD152899A5 (de)	1981-12-16

Family

ID=25690170

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD80221273A DD152899A5 (de)	1979-05-23	1980-05-21	Herbizides mittel

Country Status (9)

Country	Link
EP (1)	EP0019796A1 (da)
AU (1)	AU5846480A (da)
BR (1)	BR8003243A (da)
DD (1)	DD152899A5 (da)
DK (1)	DK224880A (da)
ES (1)	ES491729A0 (da)
FI (1)	FI801579A7 (da)
IL (1)	IL60099A0 (da)
NO (1)	NO801535L (da)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5205855A (en) *	1987-08-11	1993-04-27	Suntory Limited	Herbicidally active phenoxyalkanecarboxylic acid derivatives

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB1560416A (en) *	1975-09-03	1980-02-06	Rohm & Haas	Trifluoromethylphenyl derivatives

1980
- 1980-05-13 EP EP80102660A patent/EP0019796A1/de not_active Withdrawn
- 1980-05-15 FI FI801579A patent/FI801579A7/fi not_active Application Discontinuation
- 1980-05-16 AU AU58464/80A patent/AU5846480A/en not_active Abandoned
- 1980-05-16 IL IL60099A patent/IL60099A0/xx unknown
- 1980-05-21 DD DD80221273A patent/DD152899A5/de unknown
- 1980-05-22 DK DK224880A patent/DK224880A/da unknown
- 1980-05-22 NO NO801535A patent/NO801535L/no unknown
- 1980-05-22 ES ES491729A patent/ES491729A0/es active Granted
- 1980-05-23 BR BR8003243A patent/BR8003243A/pt unknown

Also Published As

Publication number	Publication date
FI801579A7 (fi)	1980-11-24
BR8003243A (pt)	1980-12-30
AU5846480A (en)	1980-11-27
NO801535L (no)	1980-11-24
IL60099A0 (en)	1980-07-31
EP0019796A1 (de)	1980-12-10
ES8104784A1 (es)	1981-04-01
DK224880A (da)	1980-11-24
ES491729A0 (es)	1981-04-01

Publication	Publication Date	Title
DE69202536T2 (de)	1996-01-04	Acrylatverbindungen, Verfahren zu ihrer Herstellung und diese enthaltende Fungicide.
DE2546251A1 (de)	1976-04-29	Alpha- eckige klammer auf 4-(5- mono-substituiert- oder 3,5-disubstituiert-pyridyl-2-oxy)phenoxy eckige klammer zu alkancarbonsaeuren und ihre derivate
DE2531643A1 (de)	1976-01-29	Herbizide verbindungen, unkrautvertilgungsmittel, worin diese enthalten sind, und verfahren zu ihrer anwendung
DE3024316A1 (de)	1981-03-12	(delta)(pfeil hoch)2(pfeil hoch)-1,2,4-triazolin-5-on-derivate und ihre verwendung.
DE69510033T2 (de)	1999-10-28	Aryl- und heteroaryl- pyrimidine als herbizide
CH651029A5 (de)	1985-08-30	Triazolin-derivate, verfahren zu ihrer herstellung und sie enthaltende herbizide mittel.
CH644371A5 (de)	1984-07-31	In 2- und 4-stellung disubstituierte 5-thiazolcarbonsaeuren und deren funktionelle derivate.
DD149013A5 (de)	1981-06-24	Herbizides und pflanzenregulierendes mittel
DE3514057C2 (da)	1988-04-14
EP0003805A1 (de)	1979-09-05	Pyridazonverbindungen und diese enthaltende herbizide Zusammensetzungen
DE69017383T2 (de)	1995-06-29	Substituierte bicycloheptadionderivate.
DE2630140A1 (de)	1977-01-27	Neu pyrimidin-derivate
EP0112280B1 (de)	1990-08-29	2-Aryl-4,6-dihalogenpyrimidine als Gegenmittel zum Schützen von Kulturpflanzen vor durch Herbizide verursachten phytotoxischen Schäden
CH615156A5 (da)	1980-01-15
DE69612611T2 (de)	2001-09-06	Triazin-derivate
DD231716A5 (de)	1986-01-08	Herbizide mittel
CH644096A5 (de)	1984-07-13	N-benzylhalogenacetamidderivate.
EP0007089B1 (de)	1981-09-16	Acylanilide mit herbicider und fungicider Wirkung, Verfahren zu ihrer Herstellung und ihre Verwendung
EP0062254A1 (de)	1982-10-13	Substituierte Acetanilide, Verfahren zu ihrer Herstellung und ihre Verwendung als Herbizide
EP0054715A2 (de)	1982-06-30	Propionsäureester, Herstellung dieser Verbindungen, Unkrautbekämpfungsmittel, die diese Verbindungen als Wirkstoffe enthalten, sowie Verwendung solcher Verbindungen und Mittel zur Bekämpfung von Unkräutern
DD152899A5 (de)	1981-12-16	Herbizides mittel
EP0057367B1 (de)	1983-12-28	2-Pyridyloxyacetanilid-Verbindungen, Verfahren zu ihrer Herstellung und ihre Verwendung
DE2918541A1 (de)	1979-11-15	Diphenylaminderivate und verfahren zu deren herstellung
DD262992A5 (de)	1988-12-21	Nematizide und insektizide zusammensetzung
CH639960A5 (de)	1983-12-15	2,3-dicyanopyrazin-derivate, verfahren zu deren herstellung und diese enthaltende herbizide.