DD145363A5 - Herbizide mittel - Google Patents

Herbizide mittel Download PDF

Info

Publication number: DD145363A5
Authority: DD; German Democratic Republic
Prior art keywords: alkyl; halogen; alkoxy; formula; phenyl
Prior art date: 1977-10-29

Application number

DD78208662A

Other languages

German (de)

English (en)

Inventor

Gerhard Hoerlein

Hans Juergen Nestler

Helmut Koecher

Peter Langelueddeke

Original Assignee

Hoechst Ag

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1977-10-29

Filing date

1978-10-25

Publication date

1980-12-10

1978-10-25 Application filed by Hoechst Ag filed Critical Hoechst Ag

1980-12-10 Publication of DD145363A5 publication Critical patent/DD145363A5/de

Links

239000004009 herbicide Substances 0.000 title claims abstract description 13
230000002363 herbicidal effect Effects 0.000 title claims description 13
229910052736 halogen Chemical group 0.000 claims abstract description 25
150000002367 halogens Chemical group 0.000 claims abstract description 24
125000000217 alkyl group Chemical group 0.000 claims abstract description 8
-1 methoxy-ethoxy-ethoxy Chemical group 0.000 claims description 75
150000001875 compounds Chemical class 0.000 claims description 31
239000004480 active ingredient Substances 0.000 claims description 22
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 21
239000000203 mixture Substances 0.000 claims description 20
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 10
229910052739 hydrogen Inorganic materials 0.000 claims description 8
239000001257 hydrogen Substances 0.000 claims description 8
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
125000005843 halogen group Chemical group 0.000 claims description 6
125000003342 alkenyl group Chemical group 0.000 claims description 5
125000006704 (C5-C6) cycloalkyl group Chemical group 0.000 claims description 4
239000003795 chemical substances by application Substances 0.000 claims description 4
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 4
CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 claims description 4
125000006536 (C1-C2)alkoxy group Chemical group 0.000 claims description 3
125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 3
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 3
150000001768 cations Chemical class 0.000 claims description 3
PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims description 3
125000004356 hydroxy functional group Chemical group O* 0.000 claims description 3
125000000466 oxiranyl group Chemical group 0.000 claims description 3
125000005059 halophenyl group Chemical group 0.000 claims description 2
150000007529 inorganic bases Chemical class 0.000 claims description 2
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 2
125000006501 nitrophenyl group Chemical group 0.000 claims description 2
150000007530 organic bases Chemical class 0.000 claims description 2
239000004094 surface-active agent Substances 0.000 claims 11
239000004606 Fillers/Extenders Substances 0.000 claims 10
125000003545 alkoxy group Chemical group 0.000 claims 2
125000006526 (C1-C2) alkyl group Chemical group 0.000 claims 1
125000004429 atom Chemical group 0.000 claims 1
125000000392 cycloalkenyl group Chemical group 0.000 claims 1
125000001188 haloalkyl group Chemical group 0.000 claims 1
229910052794 bromium Inorganic materials 0.000 abstract description 4
229910052801 chlorine Inorganic materials 0.000 abstract description 4
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract description 3
KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 abstract description 2
125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 abstract description 2
125000002485 formyl group Chemical class [H]C(*)=O 0.000 abstract description 2
150000002825 nitriles Chemical class 0.000 abstract description 2
150000004786 2-naphthols Chemical class 0.000 abstract 1
DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 abstract 1
JWAZRIHNYRIHIV-UHFFFAOYSA-N beta-hydroxynaphthyl Natural products C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 abstract 1
XEVRDFDBXJMZFG-UHFFFAOYSA-N carbonyl dihydrazine Chemical compound NNC(=O)NN XEVRDFDBXJMZFG-UHFFFAOYSA-N 0.000 abstract 1
150000007942 carboxylates Chemical class 0.000 abstract 1
150000001733 carboxylic acid esters Chemical class 0.000 abstract 1
AEOCXXJPGCBFJA-UHFFFAOYSA-N ethionamide Chemical compound CCC1=CC(C(N)=S)=CC=N1 AEOCXXJPGCBFJA-UHFFFAOYSA-N 0.000 abstract 1
150000002923 oximes Chemical class 0.000 abstract 1
125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 abstract 1
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 45
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
239000002253 acid Substances 0.000 description 16
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 15
239000002904 solvent Substances 0.000 description 15
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 14
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 14
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 14
239000000243 solution Substances 0.000 description 14
241000196324 Embryophyta Species 0.000 description 13
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 12
HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 11
239000000460 chlorine Substances 0.000 description 10
239000000126 substance Substances 0.000 description 10
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 8
238000009835 boiling Methods 0.000 description 8
238000001816 cooling Methods 0.000 description 8
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
238000006243 chemical reaction Methods 0.000 description 7
150000002148 esters Chemical class 0.000 description 7
238000000034 method Methods 0.000 description 7
230000035484 reaction time Effects 0.000 description 7
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
239000008187 granular material Substances 0.000 description 6
238000010992 reflux Methods 0.000 description 6
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 5
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 5
150000007513 acids Chemical class 0.000 description 5
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 5
239000004495 emulsifiable concentrate Substances 0.000 description 5
238000001704 evaporation Methods 0.000 description 5
230000008020 evaporation Effects 0.000 description 5
238000009472 formulation Methods 0.000 description 5
239000000463 material Substances 0.000 description 5
150000003254 radicals Chemical class 0.000 description 5
150000003839 salts Chemical class 0.000 description 5
239000000741 silica gel Substances 0.000 description 5
229910002027 silica gel Inorganic materials 0.000 description 5
239000008096 xylene Substances 0.000 description 5
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
239000013543 active substance Substances 0.000 description 4
150000001408 amides Chemical class 0.000 description 4
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
238000010438 heat treatment Methods 0.000 description 4
IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 4
229910000027 potassium carbonate Inorganic materials 0.000 description 4
235000011181 potassium carbonates Nutrition 0.000 description 4
239000000843 powder Substances 0.000 description 4
238000002360 preparation method Methods 0.000 description 4
235000019260 propionic acid Nutrition 0.000 description 4
229910052708 sodium Inorganic materials 0.000 description 4
239000011734 sodium Substances 0.000 description 4
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 3
RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
RJUFJBKOKNCXHH-UHFFFAOYSA-N Methyl propionate Chemical compound CCC(=O)OC RJUFJBKOKNCXHH-UHFFFAOYSA-N 0.000 description 3
238000005481 NMR spectroscopy Methods 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
150000001298 alcohols Chemical class 0.000 description 3
150000001299 aldehydes Chemical class 0.000 description 3
239000002585 base Substances 0.000 description 3
238000004821 distillation Methods 0.000 description 3
238000001035 drying Methods 0.000 description 3
239000000706 filtrate Substances 0.000 description 3
229940042795 hydrazides for tuberculosis treatment Drugs 0.000 description 3
239000002244 precipitate Substances 0.000 description 3
239000000047 product Substances 0.000 description 3
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 3
239000011833 salt mixture Substances 0.000 description 3
159000000000 sodium salts Chemical class 0.000 description 3
239000007787 solid Substances 0.000 description 3
239000007858 starting material Substances 0.000 description 3
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
239000000080 wetting agent Substances 0.000 description 3
RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 2
XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 2
GXJQMKFJQFGQKV-KHPPLWFESA-N 2-[methyl-[(z)-octadec-9-enoyl]amino]ethanesulfonic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)N(C)CCS(O)(=O)=O GXJQMKFJQFGQKV-KHPPLWFESA-N 0.000 description 2
RIUQKHCZBXLKPQ-UHFFFAOYSA-N 2-naphthalen-2-yloxyphenol Chemical class OC1=CC=CC=C1OC1=CC=C(C=CC=C2)C2=C1 RIUQKHCZBXLKPQ-UHFFFAOYSA-N 0.000 description 2
QRSXHTQQZWVKOB-UHFFFAOYSA-N 4-naphthalen-2-yloxyphenol Chemical compound C1=CC(O)=CC=C1OC1=CC=C(C=CC=C2)C2=C1 QRSXHTQQZWVKOB-UHFFFAOYSA-N 0.000 description 2
OZJPLYNZGCXSJM-UHFFFAOYSA-N 5-valerolactone Chemical compound O=C1CCCCO1 OZJPLYNZGCXSJM-UHFFFAOYSA-N 0.000 description 2
241001621841 Alopecurus myosuroides Species 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
244000058871 Echinochloa crus-galli Species 0.000 description 2
244000068988 Glycine max Species 0.000 description 2
235000010469 Glycine max Nutrition 0.000 description 2
244000100545 Lolium multiflorum Species 0.000 description 2
240000004658 Medicago sativa Species 0.000 description 2
235000017587 Medicago sativa ssp. sativa Nutrition 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
REYJJPSVUYRZGE-UHFFFAOYSA-N Octadecylamine Chemical class CCCCCCCCCCCCCCCCCCN REYJJPSVUYRZGE-UHFFFAOYSA-N 0.000 description 2
235000011999 Panicum crusgalli Nutrition 0.000 description 2
XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 2
235000008515 Setaria glauca Nutrition 0.000 description 2
244000010062 Setaria pumila Species 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
235000021307 Triticum Nutrition 0.000 description 2
244000098338 Triticum aestivum Species 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
239000012141 concentrate Substances 0.000 description 2
235000008504 concentrate Nutrition 0.000 description 2
230000018044 dehydration Effects 0.000 description 2
238000006297 dehydration reaction Methods 0.000 description 2
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 2
239000002270 dispersing agent Substances 0.000 description 2
239000003814 drug Substances 0.000 description 2
229940079593 drug Drugs 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
239000003337 fertilizer Substances 0.000 description 2
150000004820 halides Chemical class 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
125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
239000003921 oil Substances 0.000 description 2
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 2
230000020477 pH reduction Effects 0.000 description 2
150000002989 phenols Chemical class 0.000 description 2
TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 2
229940080818 propionamide Drugs 0.000 description 2
239000012429 reaction media Substances 0.000 description 2
238000000926 separation method Methods 0.000 description 2
HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 2
239000000725 suspension Substances 0.000 description 2
239000000454 talc Substances 0.000 description 2
229910052623 talc Inorganic materials 0.000 description 2
150000007970 thio esters Chemical class 0.000 description 2
239000004563 wettable powder Substances 0.000 description 2
125000004400 (C1-C12) alkyl group Chemical group 0.000 description 1
125000004890 (C1-C6) alkylamino group Chemical group 0.000 description 1
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
238000005160 1H NMR spectroscopy Methods 0.000 description 1
VKLMKIHNRDQMMY-UHFFFAOYSA-N 2-(4-naphthalen-2-yloxyphenoxy)propanamide Chemical compound C1=CC(OC(C)C(N)=O)=CC=C1OC1=CC=C(C=CC=C2)C2=C1 VKLMKIHNRDQMMY-UHFFFAOYSA-N 0.000 description 1
ONIKNECPXCLUHT-UHFFFAOYSA-N 2-chlorobenzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1Cl ONIKNECPXCLUHT-UHFFFAOYSA-N 0.000 description 1
NYEWDMNOXFGGDX-UHFFFAOYSA-N 2-chlorocyclohexan-1-ol Chemical compound OC1CCCCC1Cl NYEWDMNOXFGGDX-UHFFFAOYSA-N 0.000 description 1
MAYJUJUXGCDPPX-UHFFFAOYSA-N 2-methylpropyl 2-bromopropanoate Chemical compound CC(C)COC(=O)C(C)Br MAYJUJUXGCDPPX-UHFFFAOYSA-N 0.000 description 1
FOGYNLXERPKEGN-UHFFFAOYSA-N 3-(2-hydroxy-3-methoxyphenyl)-2-[2-methoxy-4-(3-sulfopropyl)phenoxy]propane-1-sulfonic acid Chemical compound COC1=CC=CC(CC(CS(O)(=O)=O)OC=2C(=CC(CCCS(O)(=O)=O)=CC=2)OC)=C1O FOGYNLXERPKEGN-UHFFFAOYSA-N 0.000 description 1
JPLBWCCELAOKOU-UHFFFAOYSA-N 3-naphthalen-1-yloxypropanoic acid Chemical class C1=CC=C2C(OCCC(=O)O)=CC=CC2=C1 JPLBWCCELAOKOU-UHFFFAOYSA-N 0.000 description 1
JZXBLXSDESYOAZ-UHFFFAOYSA-N 4-(1-chloronaphthalen-2-yl)oxyphenol Chemical compound ClC1=C(C=CC2=CC=CC=C12)OC1=CC=C(C=C1)O JZXBLXSDESYOAZ-UHFFFAOYSA-N 0.000 description 1
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 1
244000291564 Allium cepa Species 0.000 description 1
239000005995 Aluminium silicate Substances 0.000 description 1
244000237956 Amaranthus retroflexus Species 0.000 description 1
235000013479 Amaranthus retroflexus Nutrition 0.000 description 1
235000017060 Arachis glabrata Nutrition 0.000 description 1
244000105624 Arachis hypogaea Species 0.000 description 1
235000010777 Arachis hypogaea Nutrition 0.000 description 1
235000018262 Arachis monticola Nutrition 0.000 description 1
241000219310 Beta vulgaris subsp. vulgaris Species 0.000 description 1
244000025254 Cannabis sativa Species 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 description 1
241000288140 Gruiformes Species 0.000 description 1
239000005909 Kieselgur Substances 0.000 description 1
229910010082 LiAlH Inorganic materials 0.000 description 1
229920001732 Lignosulfonate Polymers 0.000 description 1
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical class CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
244000061176 Nicotiana tabacum Species 0.000 description 1
235000002637 Nicotiana tabacum Nutrition 0.000 description 1
240000007594 Oryza sativa Species 0.000 description 1
235000007164 Oryza sativa Nutrition 0.000 description 1
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
239000004372 Polyvinyl alcohol Substances 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
239000006004 Quartz sand Substances 0.000 description 1
208000037656 Respiratory Sounds Diseases 0.000 description 1
239000002262 Schiff base Substances 0.000 description 1
150000004753 Schiff bases Chemical class 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
235000021536 Sugar beet Nutrition 0.000 description 1
240000006677 Vicia faba Species 0.000 description 1
235000010749 Vicia faba Nutrition 0.000 description 1
235000002098 Vicia faba var. major Nutrition 0.000 description 1
NJVHJTQSGGRHGP-UHFFFAOYSA-K [Li].[Al+3].[Cl-].[Cl-].[Cl-] Chemical compound [Li].[Al+3].[Cl-].[Cl-].[Cl-] NJVHJTQSGGRHGP-UHFFFAOYSA-K 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
238000006359 acetalization reaction Methods 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 1
230000010933 acylation Effects 0.000 description 1
238000005917 acylation reaction Methods 0.000 description 1
239000000654 additive Substances 0.000 description 1
239000000853 adhesive Substances 0.000 description 1
230000001070 adhesive effect Effects 0.000 description 1
230000000274 adsorptive effect Effects 0.000 description 1
239000003513 alkali Substances 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
150000008041 alkali metal carbonates Chemical class 0.000 description 1
229910000272 alkali metal oxide Inorganic materials 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
125000004183 alkoxy alkyl group Chemical group 0.000 description 1
125000003282 alkyl amino group Chemical group 0.000 description 1
125000004414 alkyl thio group Chemical group 0.000 description 1
235000012211 aluminium silicate Nutrition 0.000 description 1
230000009435 amidation Effects 0.000 description 1
238000007112 amidation reaction Methods 0.000 description 1
150000007854 aminals Chemical class 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
239000000010 aprotic solvent Substances 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
239000003849 aromatic solvent Substances 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
229960000892 attapulgite Drugs 0.000 description 1
239000000440 bentonite Substances 0.000 description 1
229910000278 bentonite Inorganic materials 0.000 description 1
SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
150000004649 carbonic acid derivatives Chemical class 0.000 description 1
125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 1
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
239000000969 carrier Substances 0.000 description 1
238000012512 characterization method Methods 0.000 description 1
125000001309 chloro group Chemical group Cl* 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
238000003776 cleavage reaction Methods 0.000 description 1
244000038559 crop plants Species 0.000 description 1
239000012043 crude product Substances 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
229940117389 dichlorobenzene Drugs 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
239000006185 dispersion Substances 0.000 description 1
239000000428 dust Substances 0.000 description 1
230000000694 effects Effects 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
230000032050 esterification Effects 0.000 description 1
238000005886 esterification reaction Methods 0.000 description 1
LZCLXQDLBQLTDK-BYPYZUCNSA-N ethyl (2S)-lactate Chemical compound CCOC(=O)[C@H](C)O LZCLXQDLBQLTDK-BYPYZUCNSA-N 0.000 description 1
ARFLASKVLJTEJD-UHFFFAOYSA-N ethyl 2-bromopropanoate Chemical compound CCOC(=O)C(C)Br ARFLASKVLJTEJD-UHFFFAOYSA-N 0.000 description 1
239000000945 filler Substances 0.000 description 1
238000005755 formation reaction Methods 0.000 description 1
239000000417 fungicide Substances 0.000 description 1
239000003979 granulating agent Substances 0.000 description 1
238000000227 grinding Methods 0.000 description 1
239000003102 growth factor Substances 0.000 description 1
150000002429 hydrazines Chemical class 0.000 description 1
230000000977 initiatory effect Effects 0.000 description 1
239000002917 insecticide Substances 0.000 description 1
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 1
239000007788 liquid Substances 0.000 description 1
239000012280 lithium aluminium hydride Substances 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
125000005905 mesyloxy group Chemical group 0.000 description 1
229910052987 metal hydride Inorganic materials 0.000 description 1
150000004681 metal hydrides Chemical class 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
JLEJCNOTNLZCHQ-UHFFFAOYSA-N methyl 2-chloropropanoate Chemical compound COC(=O)C(C)Cl JLEJCNOTNLZCHQ-UHFFFAOYSA-N 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
239000002480 mineral oil Substances 0.000 description 1
125000001624 naphthyl group Chemical group 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical class CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
229910052625 palygorskite Inorganic materials 0.000 description 1
235000020232 peanut Nutrition 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
239000012071 phase Substances 0.000 description 1
RLOWWWKZYUNIDI-UHFFFAOYSA-N phosphinic chloride Chemical compound ClP=O RLOWWWKZYUNIDI-UHFFFAOYSA-N 0.000 description 1
230000008635 plant growth Effects 0.000 description 1
229920001495 poly(sodium acrylate) polymer Polymers 0.000 description 1
229920002451 polyvinyl alcohol Polymers 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
GHKGUEZUGFJUEJ-UHFFFAOYSA-M potassium;4-methylbenzenesulfonate Chemical compound [K+].CC1=CC=C(S([O-])(=O)=O)C=C1 GHKGUEZUGFJUEJ-UHFFFAOYSA-M 0.000 description 1
ZGJADVGJIVEEGF-UHFFFAOYSA-M potassium;phenoxide Chemical class [K+].[O-]C1=CC=CC=C1 ZGJADVGJIVEEGF-UHFFFAOYSA-M 0.000 description 1
235000014483 powder concentrate Nutrition 0.000 description 1
150000003141 primary amines Chemical class 0.000 description 1
TVDSBUOJIPERQY-UHFFFAOYSA-N prop-2-yn-1-ol Chemical compound OCC#C TVDSBUOJIPERQY-UHFFFAOYSA-N 0.000 description 1
239000003586 protic polar solvent Substances 0.000 description 1
239000008262 pumice Substances 0.000 description 1
238000000746 purification Methods 0.000 description 1
239000012264 purified product Substances 0.000 description 1
239000010453 quartz Substances 0.000 description 1
206010037833 rales Diseases 0.000 description 1
230000009467 reduction Effects 0.000 description 1
238000006722 reduction reaction Methods 0.000 description 1
235000009566 rice Nutrition 0.000 description 1
239000004576 sand Substances 0.000 description 1
238000007127 saponification reaction Methods 0.000 description 1
230000007017 scission Effects 0.000 description 1
150000003335 secondary amines Chemical class 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
NNMHYFLPFNGQFZ-UHFFFAOYSA-M sodium polyacrylate Chemical compound [Na+].[O-]C(=O)C=C NNMHYFLPFNGQFZ-UHFFFAOYSA-M 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
VWNTXBOIKQOLIX-UHFFFAOYSA-M sodium;4-naphthalen-2-yloxyphenolate Chemical compound [Na+].C1=CC([O-])=CC=C1OC1=CC=C(C=CC=C2)C2=C1 VWNTXBOIKQOLIX-UHFFFAOYSA-M 0.000 description 1
238000009331 sowing Methods 0.000 description 1
238000005507 spraying Methods 0.000 description 1
125000005415 substituted alkoxy group Chemical group 0.000 description 1
150000003871 sulfonates Chemical class 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
150000003556 thioamides Chemical class 0.000 description 1
125000005490 tosylate group Chemical group 0.000 description 1
238000005809 transesterification reaction Methods 0.000 description 1
JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
230000000007 visual effect Effects 0.000 description 1
238000010792 warming Methods 0.000 description 1
238000009736 wetting Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/18—Preparation of ethers by reactions not forming ether-oxygen bonds
- C07C41/26—Preparation of ethers by reactions not forming ether-oxygen bonds by introduction of hydroxy or O-metal groups
- 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
- 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
- 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
- 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
- A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
- A01N47/12—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing a —O—CO—N< group, or a thio analogue thereof, neither directly attached to a ring nor the nitrogen atom being a member of a heterocyclic ring
- 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
- A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
- A01N47/16—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof the nitrogen atom being part of a heterocyclic ring
- 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
- A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
- A01N47/20—N-Aryl derivatives thereof
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/257—Ethers having an ether-oxygen atom bound to carbon atoms both belonging to six-membered aromatic rings
- C07C43/295—Ethers having an ether-oxygen atom bound to carbon atoms both belonging to six-membered aromatic rings containing hydroxy or O-metal groups
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/58—Unsaturated compounds containing ether groups, groups, groups, or groups
- C07C59/64—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings
- C07C59/66—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings the non-carboxylic part of the ether containing six-membered aromatic rings
- C07C59/68—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings the non-carboxylic part of the ether containing six-membered aromatic rings the oxygen atom of the ether group being bound to a non-condensed six-membered aromatic ring
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/04—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D307/10—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/12—Radicals substituted by oxygen atoms

Landscapes

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

DD78208662A 1977-10-29 1978-10-25 Herbizide mittel DD145363A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE19772748658 DE2748658A1 (de)	1977-10-29	1977-10-29	Herbizide beta-naphthyl-phenylaether

Publications (1)

Publication Number	Publication Date
DD145363A5 true DD145363A5 (de)	1980-12-10

Family

ID=6022626

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD78208662A DD145363A5 (de)	1977-10-29	1978-10-25	Herbizide mittel

Country Status (18)

Country	Link
EP (1)	EP0001804B1 (fr)
JP (1)	JPS5470250A (fr)
AR (1)	AR225887A1 (fr)
AT (1)	AT365406B (fr)
AU (1)	AU522476B2 (fr)
BR (1)	BR7807102A (fr)
CA (1)	CA1120744A (fr)
DD (1)	DD145363A5 (fr)
DE (2)	DE2748658A1 (fr)
EG (1)	EG13577A (fr)
ES (1)	ES474447A1 (fr)
GR (1)	GR72089B (fr)
IL (1)	IL55841A (fr)
IT (1)	IT1099526B (fr)
OA (1)	OA06080A (fr)
PL (1)	PL112149B1 (fr)
PT (1)	PT68713A (fr)
ZA (1)	ZA786077B (fr)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
IT8048925A0 (it) *	1979-06-22	1980-06-10	Sandoz Ag	Esteri del tetraidro-2h-2-piranilmetanolo loro preparazione e loro impiego come erbicidi
GB8621689D0 (en) *	1986-09-09	1986-10-15	Ici Plc	Liquid crystal material
DE3829586A1 (de) *	1988-09-01	1990-03-22	Bayer Ag	Disubstituierte naphthaline, verfahren zur herstellung sowie deren herbizide verwendung

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS5015512B1 (fr) *	1971-06-18	1975-06-05
BE786644A (fr) *	1971-07-23	1973-01-24	Hoechst Ag	Derives d'acides phenoxy-4 phenoxy-alcane-carboxyliques leur preparation et les medicaments qui en contiennent
DE2611695A1 (de) *	1976-03-19	1977-09-29	Hoechst Ag	Herbizide mittel

1977
- 1977-10-29 DE DE19772748658 patent/DE2748658A1/de not_active Withdrawn
1978
- 1978-10-23 ES ES474447A patent/ES474447A1/es not_active Expired
- 1978-10-25 GR GR57500A patent/GR72089B/el unknown
- 1978-10-25 EP EP78101220A patent/EP0001804B1/fr not_active Expired
- 1978-10-25 DD DD78208662A patent/DD145363A5/de unknown
- 1978-10-25 DE DE7878101220T patent/DE2861852D1/de not_active Expired
- 1978-10-25 EG EG618/78A patent/EG13577A/xx active
- 1978-10-26 AU AU41069/78A patent/AU522476B2/en not_active Expired
- 1978-10-27 CA CA000314561A patent/CA1120744A/fr not_active Expired
- 1978-10-27 AR AR274257A patent/AR225887A1/es active
- 1978-10-27 ZA ZA00786077A patent/ZA786077B/xx unknown
- 1978-10-27 AT AT0768378A patent/AT365406B/de not_active IP Right Cessation
- 1978-10-27 IT IT29195/78A patent/IT1099526B/it active
- 1978-10-27 BR BR7807102A patent/BR7807102A/pt unknown
- 1978-10-27 PT PT68713A patent/PT68713A/fr unknown
- 1978-10-28 JP JP13213178A patent/JPS5470250A/ja active Pending
- 1978-10-28 OA OA56646A patent/OA06080A/fr unknown
- 1978-10-28 PL PL1978210577A patent/PL112149B1/pl unknown
- 1978-11-01 IL IL55841A patent/IL55841A/xx unknown

Also Published As

Publication number	Publication date
ES474447A1 (es)	1979-10-16
OA06080A (fr)	1981-06-30
DE2748658A1 (de)	1979-05-10
JPS5470250A (en)	1979-06-05
AU4106978A (en)	1980-05-01
AR225887A1 (es)	1982-05-14
ZA786077B (en)	1979-10-31
IT7829195A0 (it)	1978-10-27
PL112149B1 (en)	1980-09-30
EG13577A (en)	1981-12-31
IL55841A (en)	1984-05-31
DE2861852D1 (en)	1982-07-08
AU522476B2 (en)	1982-06-10
CA1120744A (fr)	1982-03-30
PT68713A (fr)	1978-11-01
EP0001804A1 (fr)	1979-05-16
BR7807102A (pt)	1979-05-08
GR72089B (fr)	1983-09-13
PL210577A1 (pl)	1979-07-02
AT365406B (de)	1982-01-11
IT1099526B (it)	1985-09-18
EP0001804B1 (fr)	1982-05-19
ATA768378A (de)	1981-06-15

Publication	Publication Date	Title
DE2640730C2 (de)	1983-08-25	Benzoxazolyloxy- und Benzothiazolyloxy-phenoxy-Verbindungen und diese enthaltende herbizide Mittel
EP0084893B1 (fr)	1987-01-14	Dérivés de 4H-3,1-benzoxazine, procédés pour leur préparation et leur utilisation dans la lutte contre la végétation indésirable
EP0000351A1 (fr)	1979-01-24	Dérivés d'acides phénoxy-phenyl-thio-alkylcarboxyliques, méthode de préparation et leur application comme herbicides et régulateurs de croissance des plantes
DD253754A5 (de)	1988-02-03	Herbizides und das pflanzenwachstum hemmendes mittel
CH626318A5 (fr)	1981-11-13
EP0066195B1 (fr)	1985-08-28	Dérivés de cyclohexane-1,3-dione, procédé pour leur préparation et leur utilisation pour combattre la croissance indésirable de plantes
DE2652384A1 (de)	1977-05-26	Neue herbizid wirksame, kernsubstituierte phenoxy-phenoxy-alkancarbonsaeurederivate und deren verwendung zur bekaempfung von ungraesern
EP0148119B1 (fr)	1989-05-03	Amides de l'acide 2-phénoxypropionique
DE2611695A1 (de)	1977-09-29	Herbizide mittel
EP0075840B1 (fr)	1987-11-11	Phényléthers hétérocycliques, procédé pour leur préparation et herbicides les contenant
EP0058639B1 (fr)	1985-08-14	Esters de l'acide 2-(4-(6-halogène-quinoxalinyl-2-oxy)-phénoxy)-propionique, leurs procédés de préparation et leur application comme herbicides et régulateurs de la croissance de plantes
EP0050097B1 (fr)	1984-12-05	Dérivés de l'acide alpha-(pyridyl-2-oxy-phénoxy)-propionique, procédé pour leur préparation et leur utilisation comme herbicide et/ou régulateurs de croissance de plantes
DD145363A5 (de)	1980-12-10	Herbizide mittel
DD202087A5 (de)	1983-08-31	Herbizide mittel
EP0010692A1 (fr)	1980-05-14	N-m-Anilidocarbamates, herbicides les contenant et procédé pour leur préparation ainsi que procédé pour contrôler la croissance de plantes indésirables
DD255730A5 (de)	1988-04-13	Verfahren zur herstellung von neuen aryloxy-phenoxyacyl-malonsaeureester-derivaten
CH626227A5 (en)	1981-11-13	Herbicide
DE2823424A1 (de)	1979-12-13	Dibenzofuranoxylakancarbonsaeure-derivate
EP0107123A1 (fr)	1984-05-02	Dérivés d'aniline, procédé pour leur préparation et leur utilisation dans la lutte contre la croissance des plantes indésirables
EP0091639B1 (fr)	1987-06-16	Dérivés d'aniline, procédé pour leur préparation et leur utilisation pour la limitation de la croissance des plantes indésirables
EP0084149B1 (fr)	1986-03-05	Phénoxyphényl urées, leur procédé de préparation et leur utilisation comme herbicide
DD254317A5 (de)	1988-02-24	Herbizide und wachstumsregulierende mittel
EP0114299A2 (fr)	1984-08-01	Dérivés de l'acide phénylglyoxylique, leur procédé de préparation et leur utilisation pour combattre la croissance indésirable de plantes
EP0086747B1 (fr)	1987-01-07	Phénoxy-phénoxy-alkanoyl-thioamides comme herbicides
DE3877217T2 (de)	1993-05-13	Herbizide organo-phosphor-verbindungen.