EP0000351A1 - Phenoxy-phenylthio-alkancarbonsäurederivate, Verfahren zu deren Herstellung und deren Verwendung als Herbizide und als Pflanzenwachstumsregulierungsmittel - Google Patents
Phenoxy-phenylthio-alkancarbonsäurederivate, Verfahren zu deren Herstellung und deren Verwendung als Herbizide und als Pflanzenwachstumsregulierungsmittel Download PDFInfo
- Publication number
- EP0000351A1 EP0000351A1 EP78100270A EP78100270A EP0000351A1 EP 0000351 A1 EP0000351 A1 EP 0000351A1 EP 78100270 A EP78100270 A EP 78100270A EP 78100270 A EP78100270 A EP 78100270A EP 0000351 A1 EP0000351 A1 EP 0000351A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- halogen
- formula
- alkoxy
- alkyl
- hydrogen
- Prior art date
- 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
Links
- 239000002253 acid Substances 0.000 title claims abstract description 9
- 238000000034 method Methods 0.000 title claims description 5
- 238000002360 preparation method Methods 0.000 title claims description 5
- 239000004009 herbicide Substances 0.000 title description 3
- 239000005648 plant growth regulator Substances 0.000 title 1
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 34
- 150000002367 halogens Chemical class 0.000 claims abstract description 34
- -1 cyano, carboxyl Chemical group 0.000 claims abstract description 24
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 18
- 239000001257 hydrogen Substances 0.000 claims abstract description 18
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 15
- 230000002363 herbicidal effect Effects 0.000 claims abstract description 12
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 11
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 10
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 7
- 150000001875 compounds Chemical class 0.000 claims description 39
- 239000004480 active ingredient Substances 0.000 claims description 24
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 8
- 150000001768 cations Chemical class 0.000 claims description 8
- 239000003795 chemical substances by application Substances 0.000 claims description 7
- 229910052757 nitrogen 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 6
- RJUFJBKOKNCXHH-UHFFFAOYSA-N Methyl propionate Chemical compound CCC(=O)OC RJUFJBKOKNCXHH-UHFFFAOYSA-N 0.000 claims description 5
- 239000002585 base Substances 0.000 claims description 4
- 238000009835 boiling Methods 0.000 claims description 4
- 125000005842 heteroatom Chemical group 0.000 claims description 4
- 229910052742 iron Inorganic materials 0.000 claims description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 3
- 229910052759 nickel Inorganic materials 0.000 claims description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 239000001301 oxygen Substances 0.000 claims description 3
- 125000006569 (C5-C6) heterocyclic group Chemical group 0.000 claims description 2
- SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical compound [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 claims description 2
- 239000003513 alkali Substances 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 229910052802 copper Inorganic materials 0.000 claims description 2
- 229910052748 manganese Inorganic materials 0.000 claims description 2
- FATVVDCJBJETBI-UHFFFAOYSA-N o-methyl 2-[2-cyano-5-(2,4-dichlorophenoxy)phenyl]ethanethioate Chemical compound C1=C(C#N)C(CC(=S)OC)=CC(OC=2C(=CC(Cl)=CC=2)Cl)=C1 FATVVDCJBJETBI-UHFFFAOYSA-N 0.000 claims description 2
- 230000008635 plant growth Effects 0.000 claims description 2
- 239000011541 reaction mixture Substances 0.000 claims description 2
- 230000001105 regulatory effect Effects 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 239000011593 sulfur Substances 0.000 claims description 2
- 229910052725 zinc Inorganic materials 0.000 claims description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- NQDASYBETQGUOG-UHFFFAOYSA-N O-methyl 2-[2-chloro-5-[2-nitro-4-(trifluoromethyl)phenoxy]phenyl]ethanethioate Chemical compound COC(CC1=CC(=CC=C1Cl)OC1=C(C=C(C=C1)C(F)(F)F)[N+](=O)[O-])=S NQDASYBETQGUOG-UHFFFAOYSA-N 0.000 claims 1
- 239000000010 aprotic solvent Substances 0.000 claims 1
- 239000011230 binding agent Substances 0.000 claims 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 1
- 229910052794 bromium Inorganic materials 0.000 claims 1
- 239000000460 chlorine Substances 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract description 14
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 abstract description 8
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract description 6
- 230000000694 effects Effects 0.000 abstract description 3
- 230000002401 inhibitory effect Effects 0.000 abstract description 3
- 125000003545 alkoxy group Chemical group 0.000 abstract description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 abstract description 2
- 150000001408 amides Chemical class 0.000 abstract 1
- 150000001734 carboxylic acid salts Chemical class 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- HHVIBTZHLRERCL-UHFFFAOYSA-N sulfonyldimethane Chemical group CS(C)(=O)=O HHVIBTZHLRERCL-UHFFFAOYSA-N 0.000 abstract 1
- 150000007970 thio esters Chemical class 0.000 abstract 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 24
- 239000000243 solution Substances 0.000 description 21
- 241000196324 Embryophyta Species 0.000 description 20
- 239000000203 mixture Substances 0.000 description 15
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- 239000000839 emulsion Substances 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 9
- 239000005995 Aluminium silicate Substances 0.000 description 8
- 235000012211 aluminium silicate Nutrition 0.000 description 8
- 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 8
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 8
- 239000012141 concentrate Substances 0.000 description 7
- 239000008187 granular material Substances 0.000 description 7
- 240000007594 Oryza sativa Species 0.000 description 6
- 239000013543 active substance Substances 0.000 description 6
- 241000209504 Poaceae Species 0.000 description 5
- 235000013339 cereals Nutrition 0.000 description 5
- 230000012010 growth Effects 0.000 description 5
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 5
- 239000004563 wettable powder Substances 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 4
- 235000007164 Oryza sativa Nutrition 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- 229920000151 polyglycol Polymers 0.000 description 4
- 239000010695 polyglycol Substances 0.000 description 4
- 235000009566 rice Nutrition 0.000 description 4
- 235000010288 sodium nitrite Nutrition 0.000 description 4
- XILPLWOGHPSJBK-UHFFFAOYSA-N 1,2-dichloro-4-(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=C(Cl)C(Cl)=C1 XILPLWOGHPSJBK-UHFFFAOYSA-N 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 239000002202 Polyethylene glycol Substances 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 3
- 241001233957 eudicotyledons Species 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- YDCHPLOFQATIDS-UHFFFAOYSA-N methyl 2-bromoacetate Chemical compound COC(=O)CBr YDCHPLOFQATIDS-UHFFFAOYSA-N 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 229920001223 polyethylene glycol Polymers 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 238000012545 processing Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000007921 spray Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 description 2
- HFZWRUODUSTPEG-UHFFFAOYSA-N 2,4-dichlorophenol Chemical compound OC1=CC=C(Cl)C=C1Cl HFZWRUODUSTPEG-UHFFFAOYSA-N 0.000 description 2
- KFOOSZAEJSXBFW-UHFFFAOYSA-N 4-chloro-3-methylsulfanylphenol Chemical compound CSC1=CC(O)=CC=C1Cl KFOOSZAEJSXBFW-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 244000025254 Cannabis sativa Species 0.000 description 2
- 244000108484 Cyperus difformis Species 0.000 description 2
- 240000005979 Hordeum vulgare Species 0.000 description 2
- 235000007340 Hordeum vulgare Nutrition 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- 244000061176 Nicotiana tabacum Species 0.000 description 2
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical group C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- 241000341978 Rotala Species 0.000 description 2
- 241000209056 Secale 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
- 244000098338 Triticum aestivum Species 0.000 description 2
- 229960000583 acetic acid Drugs 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000004495 emulsifiable concentrate Substances 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- FKRCODPIKNYEAC-UHFFFAOYSA-N ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- 230000009036 growth inhibition Effects 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- ACEONLNNWKIPTM-UHFFFAOYSA-N methyl 2-bromopropanoate Chemical compound COC(=O)C(C)Br ACEONLNNWKIPTM-UHFFFAOYSA-N 0.000 description 2
- LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 description 2
- 230000017066 negative regulation of growth Effects 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- PEEXCRJDFUVJRT-UHFFFAOYSA-M potassium;methoxymethanedithioate Chemical compound [K+].COC([S-])=S PEEXCRJDFUVJRT-UHFFFAOYSA-M 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000009331 sowing Methods 0.000 description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 1
- CMVNVZBFBWZFGS-UHFFFAOYSA-N 1-chloro-4-[2-chloro-4-(trifluoromethyl)phenoxy]-2-methylsulfanylbenzene Chemical compound ClC1=C(OC=2C=C(C(=CC2)Cl)SC)C=CC(=C1)C(F)(F)F CMVNVZBFBWZFGS-UHFFFAOYSA-N 0.000 description 1
- SWSMEMLPLWIMQI-UHFFFAOYSA-N 1-chloro-4-methoxy-2-methylsulfanylbenzene Chemical compound COC1=CC=C(Cl)C(SC)=C1 SWSMEMLPLWIMQI-UHFFFAOYSA-N 0.000 description 1
- XFGREQNKHBJOMT-UHFFFAOYSA-N 2,4-bis(2,4-dichlorophenoxy)-1-nitrobenzene Chemical compound C1=C(OC=2C(=CC(Cl)=CC=2)Cl)C([N+](=O)[O-])=CC=C1OC1=CC=C(Cl)C=C1Cl XFGREQNKHBJOMT-UHFFFAOYSA-N 0.000 description 1
- VHFVFXHKABVOGA-UHFFFAOYSA-N 2,4-dichloro-1-[4-(chloromethylsulfanyl)phenoxy]benzene Chemical compound ClC1=C(OC=2C=CC(=CC2)SCCl)C=CC(=C1)Cl VHFVFXHKABVOGA-UHFFFAOYSA-N 0.000 description 1
- ALHQTXHBSCKVBT-UHFFFAOYSA-N 2-[5-(2,4-dichlorophenoxy)-2-iodophenyl]ethanethioic S-acid Chemical compound ClC1=C(OC=2C=C(C(=CC=2)I)CC(=S)O)C=CC(=C1)Cl ALHQTXHBSCKVBT-UHFFFAOYSA-N 0.000 description 1
- GTHYGSMUPQGUEL-UHFFFAOYSA-N 2-chloro-1-(4-methoxy-3-nitrophenoxy)-4-(trifluoromethyl)benzene Chemical compound C1=C([N+]([O-])=O)C(OC)=CC=C1OC1=CC=C(C(F)(F)F)C=C1Cl GTHYGSMUPQGUEL-UHFFFAOYSA-N 0.000 description 1
- GBOUQGUQUUPGLO-UHFFFAOYSA-N 2-chloro-5-methoxyaniline Chemical compound COC1=CC=C(Cl)C(N)=C1 GBOUQGUQUUPGLO-UHFFFAOYSA-N 0.000 description 1
- LCNLSFRRONIQFX-UHFFFAOYSA-N 3-methylsulfanylphenol Chemical compound CSC1=CC=CC(O)=C1 LCNLSFRRONIQFX-UHFFFAOYSA-N 0.000 description 1
- VZGFGCLDCSJQPU-UHFFFAOYSA-N 5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-methoxyaniline Chemical compound C1=C(N)C(OC)=CC=C1OC1=CC=C(C(F)(F)F)C=C1Cl VZGFGCLDCSJQPU-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 240000004585 Dactylis glomerata Species 0.000 description 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
- FVIGODVHAVLZOO-UHFFFAOYSA-N Dixanthogen Chemical compound CCOC(=S)SSC(=S)OCC FVIGODVHAVLZOO-UHFFFAOYSA-N 0.000 description 1
- 244000058871 Echinochloa crus-galli Species 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 241000410074 Festuca ovina Species 0.000 description 1
- 244000068988 Glycine max Species 0.000 description 1
- 235000010469 Glycine max Nutrition 0.000 description 1
- 235000019687 Lamb Nutrition 0.000 description 1
- 241000209510 Liliopsida Species 0.000 description 1
- 240000004296 Lolium perenne Species 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 235000002637 Nicotiana tabacum Nutrition 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 1
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical group C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 1
- 208000002193 Pain Diseases 0.000 description 1
- 241000209049 Poa pratensis Species 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical group C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 241000862632 Soja Species 0.000 description 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical group C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 1
- 235000021307 Triticum Nutrition 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 125000004414 alkyl thio group Chemical group 0.000 description 1
- DNEHKUCSURWDGO-UHFFFAOYSA-N aluminum sodium Chemical compound [Na].[Al] DNEHKUCSURWDGO-UHFFFAOYSA-N 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 238000010531 catalytic reduction reaction Methods 0.000 description 1
- 235000019993 champagne Nutrition 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 230000001276 controlling effect Effects 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000005520 cutting process Methods 0.000 description 1
- 125000000664 diazo group Chemical class [N-]=[N+]=[*] 0.000 description 1
- 239000012954 diazonium Substances 0.000 description 1
- 150000001989 diazonium salts Chemical class 0.000 description 1
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical class C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- ARFLASKVLJTEJD-UHFFFAOYSA-N ethyl 2-bromopropanoate Chemical compound CCOC(=O)C(C)Br ARFLASKVLJTEJD-UHFFFAOYSA-N 0.000 description 1
- FQTIYMRSUOADDK-UHFFFAOYSA-N ethyl 3-bromopropanoate Chemical compound CCOC(=O)CCBr FQTIYMRSUOADDK-UHFFFAOYSA-N 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- NVVZQXQBYZPMLJ-UHFFFAOYSA-N formaldehyde;naphthalene-1-sulfonic acid Chemical compound O=C.C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 NVVZQXQBYZPMLJ-UHFFFAOYSA-N 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 239000002035 hexane extract Substances 0.000 description 1
- 238000005470 impregnation Methods 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 235000021374 legumes Nutrition 0.000 description 1
- 239000011572 manganese Substances 0.000 description 1
- INBDPOJZYZJUDA-UHFFFAOYSA-N methanedithiol Chemical compound SCS INBDPOJZYZJUDA-UHFFFAOYSA-N 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Substances [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 1
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
- 231100000926 not very toxic Toxicity 0.000 description 1
- 125000001117 oleyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])/C([H])=C([H])\C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 1
- 239000006072 paste Substances 0.000 description 1
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 125000004193 piperazinyl group Chemical group 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 238000006722 reduction reaction Methods 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 230000000391 smoking effect Effects 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- SRAWNDFHGTVUNZ-UHFFFAOYSA-M sodium;3,6-dibutylnaphthalene-1-sulfonate Chemical compound [Na+].[O-]S(=O)(=O)C1=CC(CCCC)=CC2=CC(CCCC)=CC=C21 SRAWNDFHGTVUNZ-UHFFFAOYSA-M 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 125000005505 thiomorpholino group Chemical group 0.000 description 1
- 230000009105 vegetative growth Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 230000003442 weekly effect Effects 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
- C07D295/18—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
- C07D295/182—Radicals derived from carboxylic acids
- C07D295/185—Radicals derived from carboxylic acids from aliphatic carboxylic acids
-
- 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
-
- 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
- A01N41/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom
- A01N41/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom containing a sulfur-to-oxygen double bond
- A01N41/04—Sulfonic acids; Derivatives thereof
- A01N41/06—Sulfonic acid amides
-
- 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
- A01N41/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom
- A01N41/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom containing a sulfur-to-oxygen double bond
- A01N41/10—Sulfones; Sulfoxides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C327/00—Thiocarboxylic acids
Definitions
- the present invention relates to new phenoxy-phenylthio-alkanecarboxylic acid derivatives which show herbicidal and plant growth-regulating activity, processes for the preparation of these derivatives, herbicidal and plant-growth-regulating agent which contain these derivatives as active compounds and the use of the new phenoxy-phenyl-thio-alkanecarboxylic acid derivatives or the compositions containing them as herbicides and / or for regulating plant growth.
- alkyl radicals in this formula can be branched or unbranched and contain the stated number of carbon atoms.
- the alkylene bridge can be the methylene bridge, the 1- or 2-ethylene bridge can be a straight or 1- or 2-methylethyl or 1,1-dimethyl-methylene branched propylene bridge, as well as a straight or correspondingly branched butylene bridge.
- the compounds of the present invention are not very toxic to warm-blooded animals and their application poses no problems. They are stable compounds which are soluble in the usual organic solvents, such as alcohols, ethers, ketones, dimethylformamide, dimethyl sulfoxide. Application rates between 0.1 and 5 kg per hectare are normally required.
- the new active compounds of the formula I according to the present invention have herbicidal activity in the case of pre- and post-emergence use and can be used as weed compositions in monocotyledonous and dicotyledonous crops.
- This diazo solution is added dropwise at 55-60 ° to a solution of 300 ml of water, 800 ml of toluene, 225 g of potassium methyl xanthate, 85 g of sodium carbonate and 75 ml of 30% sodium hydroxide solution.
- the toluene phase is separated off. This is washed with water and, after drying over sodium sulfate in 100 ml of triethylamine, added dropwise at 70 °. 2 hours reflux, then cool and add 200 ml of 30% sodium hydroxide solution. The organic phase is separated off and distilled. 160 g of 4-chloro-3-methylmercaptoanisole are obtained.
- the new active compounds of the formula I are stable compounds which are soluble in customary organic solvents, such as alcohols, ethers, ketones, dimethylformamide, dimethyl sulfoxide, etc.
- the active substance concentrations in the agents according to the invention are 1 to 80 percent by weight and, if appropriate, can also be present in low concentrations, such as 0.05 to 1%, when used.
- biocidal active substances or agents can be added to the agents according to the invention described.
- the active substance is mixed with epichlorohydrin and dissolved in 6 parts of acetone, then polyethylene glycol and cetyl polyglycol ether are added. The solution thus obtained is sprayed onto kaolin and then evaporated in vacuo.
- the specified active ingredient is applied to the appropriate carrier substances (kaolin and chalk) and then mixed and ground with the other ingredients. Spray powder of excellent wettability and suspension is obtained. From such wettable powders, suspensions of 0.1-80% active ingredient can be obtained by dilution with water, which are suitable for weed control in plant crops.
- the active ingredient is intimately mixed and ground with the additives in suitable devices.
- a paste is obtained, from which suspensions of any desired concentration can be prepared by dilution with water.
- the new 3-phenoxy-a-phenylthioalkanecarboxylic acid derivatives of the formula I and the compositions comprising them have an excellent selective herbicidal action against weeds in various, preferably monocotyledonous crops, and they also have a plant growth-regulating action.
- a particularly preferred area of application is the selective control of, above all, dicotyledon weeds in cereal crops, especially in rice.
- the new active ingredients are preferred as e.g. 25% wettable powder or e.g. 20% emulsifiable concentrates formulated and diluted with water, applied to the plant stands post-emergent.
- Various crops and weeds are grown from the seeds in pots in the greenhouse until they reach the 4 to 6 leaf stage. Then the plants are sprayed with aqueous active ingredient emulsions (obtained from a 20% emulsifiable concentrate) in various doses. The treated plants are then under optimal conditions of light, watering, temperature (22-25 ° C) and air humidity (50-70% relative) kept. The tests were evaluated 15 days after treatment.
- Rice plants that are 25 days old are transplanted into large rectangular eternit bowls in the greenhouse. Seeds of the weeds Echinochloa crus galli, Cyperus difformis, Ammania and Rotala which are found in rice crops are then sown between the rows of rice plants.
- the bowls are well watered and kept at a temperature of approx. 25 ° and high humidity. After 12 days, when the weeds have emerged and reached the 2-3 leaf stage, the earth in the bowl is covered with a 2.5 cm high layer of water.
- the active ingredient is then applied as an emulsion concentrate by means of a pipette between the rows of plants, the emulsion concentrate being diluted and applied in such a way that it corresponds to an application amount in the field of 2 and 1 kg of active ingredient per hectare.
- the experiment is evaluated after 4 weeks.
- the tested compounds according to the present invention showed pronounced contact herbicidal activity on some plants and growth arrest on many plants as a symptom of the growth-inhibiting properties.
- Seeds of the grasses Lolium perenne, Poa pratensis, Festuca ovina and Dactylis glomerata were sown in plastic trays with soil-peat-sand mixture (6: 3: 1) and watered normally.
- the accumulated grasses were cut back to a height of 4 cm weekly and sprayed with aqueous spray liquors of an active ingredient of the formula I 40 days after sowing and 1 day after the last cut.
- the amount of active ingredient was the equivalent of 5 kg of active ingredient per hectare.
- the growth of the grasses was assessed 10 and 21 days after application.
- the active substances according to the invention cause a noticeable growth inhibition both in the grasses and in the cereals.
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Dentistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Plant Pathology (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH8426/77 | 1977-07-07 | ||
| CH842677 | 1977-07-07 | ||
| CH929/78 | 1978-01-27 | ||
| CH92978 | 1978-01-27 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| EP0000351A1 true EP0000351A1 (de) | 1979-01-24 |
Family
ID=25686139
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP78100270A Ceased EP0000351A1 (de) | 1977-07-07 | 1978-06-29 | Phenoxy-phenylthio-alkancarbonsäurederivate, Verfahren zu deren Herstellung und deren Verwendung als Herbizide und als Pflanzenwachstumsregulierungsmittel |
Country Status (15)
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0025773A1 (de) * | 1979-09-13 | 1981-03-25 | Ciba-Geigy Ag | Schwefelhaltige Alkancarbonsäurederivate mit herbizider und den Pflanzenwuchs regulierender Wirkung, deren Herstellung und Verwendung |
| EP0089573A1 (de) * | 1982-03-20 | 1983-09-28 | BASF Aktiengesellschaft | Thioalkansäure-silylalkylester, Verfahren zu ihrer Herstellung und ihre Verwendung zur Bekämpfung unerwünschten Pflanzenwuchses |
| EP0033885B1 (de) * | 1980-02-08 | 1984-03-21 | Bayer Ag | Verfahren zur Herstellung von (2-Chlor-4-trifluormethyl-phenyl)-(3-methoxy-phenyl)-ether |
Families Citing this family (62)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4419123A (en) * | 1981-10-19 | 1983-12-06 | Rohm And Haas Company | Herbicidal 4-trifluoromethyl-3'-carbon-substituted-4'-substituted diphenyl ethers |
| AU557324B2 (en) * | 1981-12-25 | 1986-12-18 | Sumitomo Chemical Company, Limited | Tetrahydro phthalimide compounds |
| JPS59212472A (ja) * | 1983-05-16 | 1984-12-01 | Sumitomo Chem Co Ltd | ４，５，６，７−テトラヒドロ−２ｈ−イソインド−ル−１，３−ジオン誘導体、その製造法およびそれを有効成分とする除草剤 |
| JPS6054362A (ja) * | 1983-08-31 | 1985-03-28 | Sumitomo Chem Co Ltd | テトラヒドロフタルイミド誘導体，その製造法およびそれを有効成分とする除草剤 |
| US4902832A (en) * | 1983-08-31 | 1990-02-20 | Sumitomo Chemical Company, Limited | 2-Substituted phenyl-4,5,6,7-tetrahydro-2H-isoindole-1,3-diones, and their production and use |
| US4600432A (en) * | 1984-07-25 | 1986-07-15 | Agro-Kanesho Co., Ltd. | Propionic acid derivatives and herbicides employing them |
| DE3875546T2 (de) * | 1987-08-05 | 1993-03-11 | Dowelanco | Herbizide fluorphenoxy-phenoxyalkancarbonsaeure und ihre derivate. |
| DE3928988A1 (de) * | 1989-09-01 | 1991-03-07 | Bayer Ag | Aryloxynaphthalinderivate |
| KR20130132555A (ko) | 2010-12-21 | 2013-12-04 | 바이엘 크롭사이언스 엘피 | 바실루스의 샌드페이퍼 돌연변이체 및 식물 성장을 향상시키고 식물 건강을 촉진하고 질병 및 해충을 방제하기 위한 그의 사용 방법 |
| EP2755485A1 (en) | 2011-09-12 | 2014-07-23 | Bayer Cropscience LP | Methods of enhancing health and/or promoting growth of a plant and/or of improving fruit ripening |
| US11079725B2 (en) | 2019-04-10 | 2021-08-03 | Deere & Company | Machine control using real-time model |
| US11672203B2 (en) | 2018-10-26 | 2023-06-13 | Deere & Company | Predictive map generation and control |
| US11589509B2 (en) | 2018-10-26 | 2023-02-28 | Deere & Company | Predictive machine characteristic map generation and control system |
| US11641800B2 (en) | 2020-02-06 | 2023-05-09 | Deere & Company | Agricultural harvesting machine with pre-emergence weed detection and mitigation system |
| US11467605B2 (en) | 2019-04-10 | 2022-10-11 | Deere & Company | Zonal machine control |
| US12069978B2 (en) | 2018-10-26 | 2024-08-27 | Deere & Company | Predictive environmental characteristic map generation and control system |
| US11957072B2 (en) | 2020-02-06 | 2024-04-16 | Deere & Company | Pre-emergence weed detection and mitigation system |
| US11240961B2 (en) | 2018-10-26 | 2022-02-08 | Deere & Company | Controlling a harvesting machine based on a geo-spatial representation indicating where the harvesting machine is likely to reach capacity |
| US11653588B2 (en) | 2018-10-26 | 2023-05-23 | Deere & Company | Yield map generation and control system |
| US11178818B2 (en) | 2018-10-26 | 2021-11-23 | Deere & Company | Harvesting machine control system with fill level processing based on yield data |
| US11234366B2 (en) | 2019-04-10 | 2022-02-01 | Deere & Company | Image selection for machine control |
| US11778945B2 (en) | 2019-04-10 | 2023-10-10 | Deere & Company | Machine control using real-time model |
| US12225846B2 (en) | 2020-02-06 | 2025-02-18 | Deere & Company | Machine control using a predictive map |
| US12329148B2 (en) | 2020-02-06 | 2025-06-17 | Deere & Company | Predictive weed map and material application machine control |
| US12035648B2 (en) | 2020-02-06 | 2024-07-16 | Deere & Company | Predictive weed map generation and control system |
| US11477940B2 (en) | 2020-03-26 | 2022-10-25 | Deere & Company | Mobile work machine control based on zone parameter modification |
| US12178158B2 (en) | 2020-10-09 | 2024-12-31 | Deere & Company | Predictive map generation and control system for an agricultural work machine |
| US11711995B2 (en) | 2020-10-09 | 2023-08-01 | Deere & Company | Machine control using a predictive map |
| US11849671B2 (en) | 2020-10-09 | 2023-12-26 | Deere & Company | Crop state map generation and control system |
| US12013245B2 (en) | 2020-10-09 | 2024-06-18 | Deere & Company | Predictive map generation and control system |
| US11849672B2 (en) | 2020-10-09 | 2023-12-26 | Deere & Company | Machine control using a predictive map |
| US11650587B2 (en) | 2020-10-09 | 2023-05-16 | Deere & Company | Predictive power map generation and control system |
| US11946747B2 (en) | 2020-10-09 | 2024-04-02 | Deere & Company | Crop constituent map generation and control system |
| US11825768B2 (en) | 2020-10-09 | 2023-11-28 | Deere & Company | Machine control using a predictive map |
| US12386354B2 (en) | 2020-10-09 | 2025-08-12 | Deere & Company | Predictive power map generation and control system |
| US11871697B2 (en) | 2020-10-09 | 2024-01-16 | Deere & Company | Crop moisture map generation and control system |
| US11592822B2 (en) | 2020-10-09 | 2023-02-28 | Deere & Company | Machine control using a predictive map |
| US11895948B2 (en) | 2020-10-09 | 2024-02-13 | Deere & Company | Predictive map generation and control based on soil properties |
| US11874669B2 (en) | 2020-10-09 | 2024-01-16 | Deere & Company | Map generation and control system |
| US11889788B2 (en) | 2020-10-09 | 2024-02-06 | Deere & Company | Predictive biomass map generation and control |
| US12069986B2 (en) | 2020-10-09 | 2024-08-27 | Deere & Company | Map generation and control system |
| US11927459B2 (en) | 2020-10-09 | 2024-03-12 | Deere & Company | Machine control using a predictive map |
| US11635765B2 (en) | 2020-10-09 | 2023-04-25 | Deere & Company | Crop state map generation and control system |
| US11474523B2 (en) | 2020-10-09 | 2022-10-18 | Deere & Company | Machine control using a predictive speed map |
| US11845449B2 (en) | 2020-10-09 | 2023-12-19 | Deere & Company | Map generation and control system |
| US11727680B2 (en) | 2020-10-09 | 2023-08-15 | Deere & Company | Predictive map generation based on seeding characteristics and control |
| US11844311B2 (en) | 2020-10-09 | 2023-12-19 | Deere & Company | Machine control using a predictive map |
| US11675354B2 (en) | 2020-10-09 | 2023-06-13 | Deere & Company | Machine control using a predictive map |
| US11983009B2 (en) | 2020-10-09 | 2024-05-14 | Deere & Company | Map generation and control system |
| US11889787B2 (en) | 2020-10-09 | 2024-02-06 | Deere & Company | Predictive speed map generation and control system |
| US12250905B2 (en) | 2020-10-09 | 2025-03-18 | Deere & Company | Machine control using a predictive map |
| US12127500B2 (en) | 2021-01-27 | 2024-10-29 | Deere & Company | Machine control using a map with regime zones |
| US12229886B2 (en) | 2021-10-01 | 2025-02-18 | Deere & Company | Historical crop state model, predictive crop state map generation and control system |
| US12310286B2 (en) | 2021-12-14 | 2025-05-27 | Deere & Company | Crop constituent sensing |
| US12302791B2 (en) | 2021-12-20 | 2025-05-20 | Deere & Company | Crop constituents, predictive mapping, and agricultural harvester control |
| US12245549B2 (en) | 2022-01-11 | 2025-03-11 | Deere & Company | Predictive response map generation and control system |
| US12082531B2 (en) | 2022-01-26 | 2024-09-10 | Deere & Company | Systems and methods for predicting material dynamics |
| US12295288B2 (en) | 2022-04-05 | 2025-05-13 | Deere &Company | Predictive machine setting map generation and control system |
| US12058951B2 (en) | 2022-04-08 | 2024-08-13 | Deere & Company | Predictive nutrient map and control |
| US12284934B2 (en) | 2022-04-08 | 2025-04-29 | Deere & Company | Systems and methods for predictive tractive characteristics and control |
| US12358493B2 (en) | 2022-04-08 | 2025-07-15 | Deere & Company | Systems and methods for predictive power requirements and control |
| US12298767B2 (en) | 2022-04-08 | 2025-05-13 | Deere & Company | Predictive material consumption map and control |
Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH424761A (de) * | 1963-06-28 | 1966-11-30 | Sandoz Ag | Verfahren zur Herstellung neuer Thiolcarbonsäureester |
| DE2130919A1 (de) * | 1970-06-22 | 1971-12-30 | Nippon Kayaku Kk | Substituierte Diphenylaether,Verfahren zu ihrer Herstellung und ihre Verwendung als Herbizide |
| DE2223894A1 (de) * | 1972-05-17 | 1973-12-13 | Hoechst Ag | Herbizide mittel |
| DE2333848A1 (de) * | 1973-07-03 | 1975-01-16 | Bayer Ag | Halogenierte 4-trifluormethyl-diphenyl (thio)aether, verfahren zu ihrer herstellung und ihre verwendung als herbizide |
| FR2285861A1 (fr) * | 1974-09-30 | 1976-04-23 | Lafon Labor | Composes diaryle soufres et diaryle oxygenes |
| FR2325638A1 (fr) * | 1975-09-27 | 1977-04-22 | Ishihara Mining & Chemical Co | Herbicides a base d'acide phenoxy phenoxy alcane carboxylique |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3784635A (en) * | 1969-04-25 | 1974-01-08 | Mobil Oil Corp | Substituted phenoxybenzoic acids and esters thereof |
-
1978
- 1978-06-29 EP EP78100270A patent/EP0000351A1/de not_active Ceased
- 1978-07-05 IL IL55085A patent/IL55085A/xx unknown
- 1978-07-05 DD DD78206536A patent/DD138142A5/xx unknown
- 1978-07-05 AR AR272847A patent/AR221487A1/es active
- 1978-07-06 TR TR20047A patent/TR20047A/xx unknown
- 1978-07-06 CA CA306,928A patent/CA1108172A/en not_active Expired
- 1978-07-06 AU AU37824/78A patent/AU522170B2/en not_active Expired
- 1978-07-06 ES ES471526A patent/ES471526A1/es not_active Expired
- 1978-07-06 HU HU78CI1838A patent/HU182473B/hu unknown
- 1978-07-06 AT AT491978A patent/AT358557B/de not_active IP Right Cessation
- 1978-07-06 IT IT25415/78A patent/IT1096916B/it active
- 1978-07-07 JP JP8281778A patent/JPS5416438A/ja active Granted
- 1978-07-07 BR BR7804382A patent/BR7804382A/pt unknown
- 1978-07-07 CS CS784551A patent/CS222267B2/cs unknown
-
1980
- 1980-09-05 US US06/184,608 patent/US4349377A/en not_active Expired - Lifetime
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH424761A (de) * | 1963-06-28 | 1966-11-30 | Sandoz Ag | Verfahren zur Herstellung neuer Thiolcarbonsäureester |
| DE2130919A1 (de) * | 1970-06-22 | 1971-12-30 | Nippon Kayaku Kk | Substituierte Diphenylaether,Verfahren zu ihrer Herstellung und ihre Verwendung als Herbizide |
| DE2223894A1 (de) * | 1972-05-17 | 1973-12-13 | Hoechst Ag | Herbizide mittel |
| DE2333848A1 (de) * | 1973-07-03 | 1975-01-16 | Bayer Ag | Halogenierte 4-trifluormethyl-diphenyl (thio)aether, verfahren zu ihrer herstellung und ihre verwendung als herbizide |
| FR2285861A1 (fr) * | 1974-09-30 | 1976-04-23 | Lafon Labor | Composes diaryle soufres et diaryle oxygenes |
| FR2325638A1 (fr) * | 1975-09-27 | 1977-04-22 | Ishihara Mining & Chemical Co | Herbicides a base d'acide phenoxy phenoxy alcane carboxylique |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0025773A1 (de) * | 1979-09-13 | 1981-03-25 | Ciba-Geigy Ag | Schwefelhaltige Alkancarbonsäurederivate mit herbizider und den Pflanzenwuchs regulierender Wirkung, deren Herstellung und Verwendung |
| EP0033885B1 (de) * | 1980-02-08 | 1984-03-21 | Bayer Ag | Verfahren zur Herstellung von (2-Chlor-4-trifluormethyl-phenyl)-(3-methoxy-phenyl)-ether |
| US4450308A (en) * | 1980-02-08 | 1984-05-22 | Bayer Aktiengesellschaft | Process for the preparation of trifluoromethylphenyl oxyphenyl ether compounds |
| EP0089573A1 (de) * | 1982-03-20 | 1983-09-28 | BASF Aktiengesellschaft | Thioalkansäure-silylalkylester, Verfahren zu ihrer Herstellung und ihre Verwendung zur Bekämpfung unerwünschten Pflanzenwuchses |
Also Published As
| Publication number | Publication date |
|---|---|
| HU182473B (en) | 1984-01-30 |
| CS222267B2 (en) | 1983-06-24 |
| BR7804382A (pt) | 1979-03-06 |
| AR221487A1 (es) | 1981-02-13 |
| AU522170B2 (en) | 1982-05-20 |
| IT1096916B (it) | 1985-08-26 |
| ATA491978A (de) | 1980-02-15 |
| IT7825415A0 (it) | 1978-07-06 |
| CA1108172A (en) | 1981-09-01 |
| TR20047A (tr) | 1980-07-02 |
| AT358557B (de) | 1980-09-25 |
| JPS6230184B2 (enrdf_load_stackoverflow) | 1987-07-01 |
| DD138142A5 (de) | 1979-10-17 |
| ES471526A1 (es) | 1979-01-16 |
| IL55085A0 (en) | 1978-09-29 |
| JPS5416438A (en) | 1979-02-07 |
| US4349377A (en) | 1982-09-14 |
| IL55085A (en) | 1983-02-23 |
| AU3782478A (en) | 1980-01-10 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP0000351A1 (de) | Phenoxy-phenylthio-alkancarbonsäurederivate, Verfahren zu deren Herstellung und deren Verwendung als Herbizide und als Pflanzenwachstumsregulierungsmittel | |
| DE2732846C2 (enrdf_load_stackoverflow) | ||
| EP0004317B1 (de) | Neue Phenoxy-alkancarbonsäurederivate, deren Herstellung, sie enthaltende herbizide Mittel und deren Verwendung | |
| EP0003114A1 (de) | Herbizid wirksame ungesättigte Ester von 4-(3',5'-Dihalogenpyridyl -(2')-oxy)-alpha-phenoxypropionsäuren, Verfahren zu ihrer Herstellung sowie sie enthaltende herbizide Mittel und deren Verwendung | |
| EP0014684A2 (de) | 2-Substituierte 5-Phenoxy-phenylphosphonsäurederivate, Verfahren zu ihrer Herstellung und ihre Verwendung als Herbizide | |
| US4394327A (en) | Herbicidally active phenoxy-α-phenoxy-alkanecarboxylic acid derivatives | |
| EP0003295B1 (de) | Neue Phenoxy-phenoxy-alkancarbonsäurederivate mit herbizider Wirkung, deren Herstellung, sie enthaltende Mittel und deren Verwendung | |
| EP0148119B1 (de) | 2-Phenoxypropions ure-cyanamide | |
| EP0036390B1 (de) | Diphenyläther-Harnstoffe mit herbizider Wirkung | |
| EP0211805A2 (de) | Neue N-(2-Fluorphenyl)-azolidine | |
| EP0058639B1 (de) | 2-(4-(6-Halogen-chinoxalinyl-2-oxy)-phenoxy)-propionsäureester, Verfahren zu ihrer Herstellung sowie ihre Verwendung als Herbizide und Pflanzenwuchsregulatoren | |
| EP0007089B1 (de) | Acylanilide mit herbicider und fungicider Wirkung, Verfahren zu ihrer Herstellung und ihre Verwendung | |
| EP0008624A1 (de) | Ester von O-(Pyridyloxy-phenyl)-milchsäuren, Verfahren zu ihrer Herstellung und ihre Verwendung als Herbizide und Pflanzenwachstumsregulatoren | |
| DE2615878A1 (de) | Polycyclische stickstoffhaltige verbindungen | |
| CH623725A5 (en) | Herbicide containing, as active substance, novel phenoxy-alpha-phenoxyalkanecarboxylic acid derivatives | |
| EP0003297B1 (de) | Neue Phenoxy-alkyl-oxazoline, deren Herstellung, sie enthaltende herbizide Mittel und deren Verwendung | |
| EP0259265B1 (de) | 3-Methylphthalimide | |
| DE2730591A1 (de) | Neue herbizid wirksame, kernsubstituierte phenoxy-phenoxy-alkancarbonsaeurederivate und deren verwendung zur bekaempfung von ungraesern | |
| EP0001641A1 (de) | 2-(2'-Nitro-5-(2"-chlor-4"-trifluormethylphenoxy)-phenoxy)-propionsäure-methoxyäthylester, ein diesen Ester als Wirkstoff enthaltendes Mittel und dessen Verwendung als Herbizid. | |
| EP0034120B1 (de) | Neue Phenoxy-phenoxy-carbonsäurederivate | |
| EP0098440B1 (de) | 3,7-Dichlor-chinolinderivate, Verfahren zu ihrer Herstellung und ihre Verwendung zur Bekämpfung unerwünschten Pflanzenwuchses | |
| DE2742034A1 (de) | Polycyclische stickstoffhaltige verbindungen | |
| EP0000359B1 (de) | Phenoxy-phenylsulfinyl- und -sulfonyl-alkancarbonsäure-Derivate, Verfahren zu deren Herstellung und deren Verwendung als Herbizide und als Pflanzenwachstumsregulierungsmittel. | |
| EP0249858B1 (de) | Fluoralkylsubstituierte Chinolinderivate. ihre Herstellung sowie Verwendung zur Bekämpfung unerwünschten Pflanzenwachstums | |
| EP0107123A1 (de) | Anilinderivate, Verfahren zu ihrer Herstellung und ihre Verwendung zur Bekämpfung unerwünschten Pflanzenwuchses |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PUAI | Public reference made under article 153(3) epc to a published international application that has entered the european phase |
Free format text: ORIGINAL CODE: 0009012 |
|
| AK | Designated contracting states |
Designated state(s): BE CH DE FR GB NL |
|
| 17P | Request for examination filed | ||
| STAA | Information on the status of an ep patent application or granted ep patent |
Free format text: STATUS: THE APPLICATION HAS BEEN REFUSED |
|
| 18R | Application refused |
Effective date: 19810804 |
|
| RIN1 | Information on inventor provided before grant (corrected) |
Inventor name: ROHR, OTTO, DR. Inventor name: DUERR, DIETER, DR. Inventor name: BOEHNER, BEAT, DR. Inventor name: PISSIOTAS, GEORG, DR. |