DD141899A5 - Herbizide mittel - Google Patents

Herbizide mittel Download PDF

Info

Publication number: DD141899A5
Authority: DD; German Democratic Republic
Prior art keywords: methyl; chloroacetanilide; aniline; ethyl; ylmethyl
Prior art date: 1978-02-10

Application number

DD79210848A

Other languages

German (de)

English (en)

Inventor

Joerg Stetter

Wilfried Draber

Rudolf Thomas

Ludwig Eue

Robert R Schmidt

Winfried Lunkenheimer

Original Assignee

Bayer 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.)

1978-02-10

Filing date

1979-02-06

Publication date

1980-05-28

1979-02-06 Application filed by Bayer Ag filed Critical Bayer Ag

1980-05-28 Publication of DD141899A5 publication Critical patent/DD141899A5/de

Links

230000002363 herbicidal effect Effects 0.000 title claims abstract description 8
239000004009 herbicide Substances 0.000 title description 6
239000000203 mixture Substances 0.000 claims abstract description 15
125000000217 alkyl group Chemical group 0.000 claims description 32
229910052736 halogen Inorganic materials 0.000 claims description 25
150000002367 halogens Chemical group 0.000 claims description 25
125000001188 haloalkyl group Chemical group 0.000 claims description 22
241000196324 Embryophyta Species 0.000 claims description 19
229910052739 hydrogen Inorganic materials 0.000 claims description 12
239000001257 hydrogen Substances 0.000 claims description 12
125000003710 aryl alkyl group Chemical group 0.000 claims description 11
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
125000003342 alkenyl group Chemical group 0.000 claims description 9
125000000304 alkynyl group Chemical group 0.000 claims description 9
125000000753 cycloalkyl group Chemical group 0.000 claims description 9
238000000034 method Methods 0.000 claims description 8
125000003107 substituted aryl group Chemical group 0.000 claims description 7
238000002360 preparation method Methods 0.000 claims description 6
239000004606 Fillers/Extenders Substances 0.000 claims description 4
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
238000002156 mixing Methods 0.000 claims description 4
229910052760 oxygen Inorganic materials 0.000 claims description 4
239000001301 oxygen Substances 0.000 claims description 4
229910052717 sulfur Inorganic materials 0.000 claims description 4
239000011593 sulfur Substances 0.000 claims description 4
239000004094 surface-active agent Substances 0.000 claims description 3
150000001875 compounds Chemical class 0.000 abstract description 33
-1 5-methyl-1,3,4-oxadiazol-2-yl-methyl Chemical group 0.000 description 128
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 76
125000004432 carbon atom Chemical group C* 0.000 description 51
239000000460 chlorine Substances 0.000 description 27
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 22
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 16
229910052801 chlorine Inorganic materials 0.000 description 16
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
VONWPEXRCLHKRJ-UHFFFAOYSA-N 2-chloro-n-phenylacetamide Chemical compound ClCC(=O)NC1=CC=CC=C1 VONWPEXRCLHKRJ-UHFFFAOYSA-N 0.000 description 12
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 12
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
229910052731 fluorine Inorganic materials 0.000 description 12
239000011737 fluorine Substances 0.000 description 12
239000002904 solvent Substances 0.000 description 12
125000005843 halogen group Chemical group 0.000 description 11
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 11
SNTWKPAKVQFCCF-UHFFFAOYSA-N 2,3-dihydro-1h-triazole Chemical compound N1NC=CN1 SNTWKPAKVQFCCF-UHFFFAOYSA-N 0.000 description 10
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
125000003118 aryl group Chemical group 0.000 description 9
239000003960 organic solvent Substances 0.000 description 9
150000003254 radicals Chemical class 0.000 description 9
239000007858 starting material Substances 0.000 description 9
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
239000002253 acid Substances 0.000 description 8
238000002844 melting Methods 0.000 description 8
230000008018 melting Effects 0.000 description 8
HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 8
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 7
125000003545 alkoxy group Chemical group 0.000 description 7
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 7
229910052794 bromium Inorganic materials 0.000 description 7
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 7
238000009472 formulation Methods 0.000 description 7
239000000126 substance Substances 0.000 description 7
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 7
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
239000004480 active ingredient Substances 0.000 description 6
125000004093 cyano group Chemical group *C#N 0.000 description 6
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 6
239000000243 solution Substances 0.000 description 6
125000004414 alkyl thio group Chemical group 0.000 description 5
239000011230 binding agent Substances 0.000 description 5
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
239000008187 granular material Substances 0.000 description 5
239000000843 powder Substances 0.000 description 5
VEUMBMHMMCOFAG-UHFFFAOYSA-N 2,3-dihydrooxadiazole Chemical compound N1NC=CO1 VEUMBMHMMCOFAG-UHFFFAOYSA-N 0.000 description 4
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 4
150000008064 anhydrides Chemical class 0.000 description 4
230000000694 effects Effects 0.000 description 4
239000003995 emulsifying agent Substances 0.000 description 4
150000002429 hydrazines Chemical class 0.000 description 4
239000003208 petroleum Substances 0.000 description 4
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
238000005554 pickling Methods 0.000 description 4
VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
125000001478 1-chloroethyl group Chemical group [H]C([H])([H])C([H])(Cl)* 0.000 description 3
JAVFLGCTQKOUTK-UHFFFAOYSA-N 2-(2,6-diethylanilino)acetohydrazide Chemical compound CCC1=CC=CC(CC)=C1NCC(=O)NN JAVFLGCTQKOUTK-UHFFFAOYSA-N 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 description 3
241000251730 Chondrichthyes Species 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
150000001338 aliphatic hydrocarbons Chemical class 0.000 description 3
150000005840 aryl radicals Chemical class 0.000 description 3
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
239000000969 carrier Substances 0.000 description 3
150000001805 chlorine compounds Chemical class 0.000 description 3
230000006378 damage Effects 0.000 description 3
238000001035 drying Methods 0.000 description 3
239000000839 emulsion Substances 0.000 description 3
150000002148 esters Chemical class 0.000 description 3
150000002170 ethers Chemical class 0.000 description 3
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 3
229910000041 hydrogen chloride Inorganic materials 0.000 description 3
238000004519 manufacturing process Methods 0.000 description 3
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 3
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
238000010992 reflux Methods 0.000 description 3
239000002689 soil Substances 0.000 description 3
239000007787 solid Substances 0.000 description 3
238000003756 stirring Methods 0.000 description 3
239000000725 suspension Substances 0.000 description 3
NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
CZZZABOKJQXEBO-UHFFFAOYSA-N 2,4-dimethylaniline Chemical compound CC1=CC=C(N)C(C)=C1 CZZZABOKJQXEBO-UHFFFAOYSA-N 0.000 description 2
VOWZNBNDMFLQGM-UHFFFAOYSA-N 2,5-dimethylaniline Chemical compound CC1=CC=C(C)C(N)=C1 VOWZNBNDMFLQGM-UHFFFAOYSA-N 0.000 description 2
UFFBMTHBGFGIHF-UHFFFAOYSA-N 2,6-dimethylaniline Chemical compound CC1=CC=CC(C)=C1N UFFBMTHBGFGIHF-UHFFFAOYSA-N 0.000 description 2
BQGOXMFAGHVQDF-UHFFFAOYSA-N 2-(chloromethyl)-1,3,4-oxadiazole Chemical compound ClCC1=NN=CO1 BQGOXMFAGHVQDF-UHFFFAOYSA-N 0.000 description 2
DCPLOIFDMMEBQZ-UHFFFAOYSA-N 2-bromo-n-phenylacetamide Chemical class BrCC(=O)NC1=CC=CC=C1 DCPLOIFDMMEBQZ-UHFFFAOYSA-N 0.000 description 2
JJVKJJNCIILLRP-UHFFFAOYSA-N 2-ethyl-6-methylaniline Chemical compound CCC1=CC=CC(C)=C1N JJVKJJNCIILLRP-UHFFFAOYSA-N 0.000 description 2
MLPVBIWIRCKMJV-UHFFFAOYSA-N 2-ethylaniline Chemical compound CCC1=CC=CC=C1N MLPVBIWIRCKMJV-UHFFFAOYSA-N 0.000 description 2
ZUVPLKVDZNDZCM-UHFFFAOYSA-N 3-chloro-2-methylaniline Chemical compound CC1=C(N)C=CC=C1Cl ZUVPLKVDZNDZCM-UHFFFAOYSA-N 0.000 description 2
CXNVOWPRHWWCQR-UHFFFAOYSA-N 4-Chloro-ortho-toluidine Chemical compound CC1=CC(Cl)=CC=C1N CXNVOWPRHWWCQR-UHFFFAOYSA-N 0.000 description 2
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
235000005781 Avena Nutrition 0.000 description 2
244000075850 Avena orientalis Species 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
239000004215 Carbon black (E152) Substances 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
235000021506 Ipomoea Nutrition 0.000 description 2
241000207783 Ipomoea Species 0.000 description 2
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical class [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
FZERHIULMFGESH-UHFFFAOYSA-N N-phenylacetamide Chemical compound CC(=O)NC1=CC=CC=C1 FZERHIULMFGESH-UHFFFAOYSA-N 0.000 description 2
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
241000209117 Panicum Species 0.000 description 2
235000006443 Panicum miliaceum subsp. miliaceum Nutrition 0.000 description 2
235000009037 Panicum miliaceum subsp. ruderale Nutrition 0.000 description 2
229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
241000207763 Solanum Species 0.000 description 2
235000002634 Solanum Nutrition 0.000 description 2
235000011684 Sorghum saccharatum Nutrition 0.000 description 2
244000062793 Sorghum vulgare Species 0.000 description 2
240000008042 Zea mays Species 0.000 description 2
235000002017 Zea mays subsp mays Nutrition 0.000 description 2
125000002877 alkyl aryl group Chemical group 0.000 description 2
150000001448 anilines Chemical class 0.000 description 2
239000002585 base Substances 0.000 description 2
HTZCNXWZYVXIMZ-UHFFFAOYSA-M benzyl(triethyl)azanium;chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC1=CC=CC=C1 HTZCNXWZYVXIMZ-UHFFFAOYSA-M 0.000 description 2
238000009835 boiling Methods 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
239000003153 chemical reaction reagent Substances 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
239000012141 concentrate Substances 0.000 description 2
244000038559 crop plants Species 0.000 description 2
239000013078 crystal Substances 0.000 description 2
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
239000003085 diluting agent Substances 0.000 description 2
VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 2
239000002270 dispersing agent Substances 0.000 description 2
239000000975 dye Substances 0.000 description 2
235000013399 edible fruits Nutrition 0.000 description 2
150000002391 heterocyclic compounds Chemical class 0.000 description 2
125000000623 heterocyclic group Chemical group 0.000 description 2
IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 2
229930195733 hydrocarbon Natural products 0.000 description 2
150000002430 hydrocarbons Chemical class 0.000 description 2
150000002463 imidates Chemical class 0.000 description 2
229910052500 inorganic mineral Inorganic materials 0.000 description 2
239000011630 iodine Substances 0.000 description 2
229910052740 iodine Inorganic materials 0.000 description 2
150000002576 ketones Chemical class 0.000 description 2
239000007788 liquid Substances 0.000 description 2
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
239000011707 mineral Substances 0.000 description 2
150000002825 nitriles Chemical class 0.000 description 2
235000015097 nutrients Nutrition 0.000 description 2
RNVCVTLRINQCPJ-UHFFFAOYSA-N o-toluidine Chemical compound CC1=CC=CC=C1N RNVCVTLRINQCPJ-UHFFFAOYSA-N 0.000 description 2
150000004866 oxadiazoles Chemical class 0.000 description 2
FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 2
229920000151 polyglycol Polymers 0.000 description 2
239000010695 polyglycol Substances 0.000 description 2
229910000027 potassium carbonate Inorganic materials 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
229910052938 sodium sulfate Inorganic materials 0.000 description 2
235000011152 sodium sulphate Nutrition 0.000 description 2
238000005507 spraying Methods 0.000 description 2
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
239000008096 xylene Substances 0.000 description 2
MBIZXFATKUQOOA-UHFFFAOYSA-N 1,3,4-thiadiazole Chemical compound C1=NN=CS1 MBIZXFATKUQOOA-UHFFFAOYSA-N 0.000 description 1
KAESVJOAVNADME-UHFFFAOYSA-N 1H-pyrrole Natural products C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 1
PAYRUJLWNCNPSJ-RALIUCGRSA-N 2,3,4,5,6-pentadeuterioaniline Chemical compound [2H]C1=C([2H])C([2H])=C(N)C([2H])=C1[2H] PAYRUJLWNCNPSJ-RALIUCGRSA-N 0.000 description 1
VVAKEQGKZNKUSU-UHFFFAOYSA-N 2,3-dimethylaniline Chemical compound CC1=CC=CC(N)=C1C VVAKEQGKZNKUSU-UHFFFAOYSA-N 0.000 description 1
BMIPMKQAAJKBKP-UHFFFAOYSA-N 2,4,5-Trimethylaniline Chemical compound CC1=CC(C)=C(N)C=C1C BMIPMKQAAJKBKP-UHFFFAOYSA-N 0.000 description 1
KWVPRPSXBZNOHS-UHFFFAOYSA-N 2,4,6-Trimethylaniline Chemical compound CC1=CC(C)=C(N)C(C)=C1 KWVPRPSXBZNOHS-UHFFFAOYSA-N 0.000 description 1
ZNXJCSBDMHIWJG-UHFFFAOYSA-N 2,6-di(propan-2-yl)-n-(1,3,4-thiadiazol-2-ylmethyl)aniline Chemical compound CC(C)C1=CC=CC(C(C)C)=C1NCC1=NN=CS1 ZNXJCSBDMHIWJG-UHFFFAOYSA-N 0.000 description 1
WKBALTUBRZPIPZ-UHFFFAOYSA-N 2,6-di(propan-2-yl)aniline Chemical compound CC(C)C1=CC=CC(C(C)C)=C1N WKBALTUBRZPIPZ-UHFFFAOYSA-N 0.000 description 1
OIXUMNZGNCAOKY-UHFFFAOYSA-N 2,6-diethyl-4-methylaniline Chemical compound CCC1=CC(C)=CC(CC)=C1N OIXUMNZGNCAOKY-UHFFFAOYSA-N 0.000 description 1
OIMRVNGMYJTNNF-UHFFFAOYSA-N 2,6-diethyl-n-(1,3,4-oxadiazol-2-ylmethyl)aniline Chemical compound CCC1=CC=CC(CC)=C1NCC1=NN=CO1 OIMRVNGMYJTNNF-UHFFFAOYSA-N 0.000 description 1
DCTZSUYBGOMMSV-UHFFFAOYSA-N 2,6-diethyl-n-[(4-methyl-5-methylsulfanyl-1,2,4-triazol-3-yl)methyl]aniline Chemical compound CCC1=CC=CC(CC)=C1NCC1=NN=C(SC)N1C DCTZSUYBGOMMSV-UHFFFAOYSA-N 0.000 description 1
IFQVRXCWHHKNAY-UHFFFAOYSA-N 2,6-diethyl-n-[(5-phenyl-1,3,4-oxadiazol-2-yl)methyl]aniline Chemical compound CCC1=CC=CC(CC)=C1NCC1=NN=C(C=2C=CC=CC=2)O1 IFQVRXCWHHKNAY-UHFFFAOYSA-N 0.000 description 1
XSLVIVUQCWABRO-UHFFFAOYSA-N 2,6-diethyl-n-[(5-phenyl-1,3,4-thiadiazol-2-yl)methyl]aniline Chemical compound CCC1=CC=CC(CC)=C1NCC1=NN=C(C=2C=CC=CC=2)S1 XSLVIVUQCWABRO-UHFFFAOYSA-N 0.000 description 1
DMAUQICHATWFIQ-UHFFFAOYSA-N 2,6-diethyl-n-[[5-(trifluoromethyl)-1,3,4-thiadiazol-2-yl]methyl]aniline Chemical compound CCC1=CC=CC(CC)=C1NCC1=NN=C(C(F)(F)F)S1 DMAUQICHATWFIQ-UHFFFAOYSA-N 0.000 description 1
FOYHNROGBXVLLX-UHFFFAOYSA-N 2,6-diethylaniline Chemical compound CCC1=CC=CC(CC)=C1N FOYHNROGBXVLLX-UHFFFAOYSA-N 0.000 description 1
BAGSBVOPSKVXJY-UHFFFAOYSA-N 2,6-dimethyl-n-[(5-propan-2-yl-1,3,4-oxadiazol-2-yl)methyl]aniline Chemical compound O1C(C(C)C)=NN=C1CNC1=C(C)C=CC=C1C BAGSBVOPSKVXJY-UHFFFAOYSA-N 0.000 description 1
OEDSGAAQMOCTAG-UHFFFAOYSA-N 2-(2,4,6-trimethylanilino)propanehydrazide Chemical compound NNC(=O)C(C)NC1=C(C)C=C(C)C=C1C OEDSGAAQMOCTAG-UHFFFAOYSA-N 0.000 description 1
MEGGCNWTMZPOBE-UHFFFAOYSA-N 2-(2,6-diethylanilino)-n-(methylaminocarbamothioyl)acetamide Chemical compound CCC1=CC=CC(CC)=C1NCC(=O)NC(=S)NNC MEGGCNWTMZPOBE-UHFFFAOYSA-N 0.000 description 1
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239000003054 catalyst Substances 0.000 description 1
235000013339 cereals Nutrition 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
150000008422 chlorobenzenes Chemical class 0.000 description 1
235000020971 citrus fruits Nutrition 0.000 description 1
239000010941 cobalt Substances 0.000 description 1
229910017052 cobalt Inorganic materials 0.000 description 1
GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
235000016213 coffee Nutrition 0.000 description 1
235000013353 coffee beverage Nutrition 0.000 description 1
238000001816 cooling Methods 0.000 description 1
229910052802 copper Inorganic materials 0.000 description 1
239000010949 copper Substances 0.000 description 1
235000005822 corn Nutrition 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
239000002837 defoliant Substances 0.000 description 1
239000002274 desiccant Substances 0.000 description 1
GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O GUJOJGAPFQRJSV-UHFFFAOYSA-N 0.000 description 1
235000014113 dietary fatty acids Nutrition 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
239000010459 dolomite Substances 0.000 description 1
229910000514 dolomite Inorganic materials 0.000 description 1
238000010410 dusting Methods 0.000 description 1
230000001804 emulsifying effect Effects 0.000 description 1
QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical group C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 description 1
UHJMECPUUCQFRL-UHFFFAOYSA-N ethyl 2-(2,6-diethylanilino)acetate Chemical compound CCOC(=O)CNC1=C(CC)C=CC=C1CC UHJMECPUUCQFRL-UHFFFAOYSA-N 0.000 description 1
241001233957 eudicotyledons Species 0.000 description 1
239000000194 fatty acid Substances 0.000 description 1
229930195729 fatty acid Natural products 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
235000013312 flour Nutrition 0.000 description 1
RZILCCPWPBTYDO-UHFFFAOYSA-N fluometuron Chemical compound CN(C)C(=O)NC1=CC=CC(C(F)(F)F)=C1 RZILCCPWPBTYDO-UHFFFAOYSA-N 0.000 description 1
235000019253 formic acid Nutrition 0.000 description 1
239000000417 fungicide Substances 0.000 description 1
238000004817 gas chromatography Methods 0.000 description 1
239000012362 glacial acetic acid Substances 0.000 description 1
239000003102 growth factor Substances 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
150000008282 halocarbons Chemical class 0.000 description 1
150000005826 halohydrocarbons Chemical class 0.000 description 1
150000004678 hydrides Chemical class 0.000 description 1
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
239000003112 inhibitor Substances 0.000 description 1
238000011081 inoculation Methods 0.000 description 1
150000007529 inorganic bases Chemical class 0.000 description 1
239000001023 inorganic pigment Substances 0.000 description 1
239000002917 insecticide Substances 0.000 description 1
229910052742 iron Inorganic materials 0.000 description 1
239000012948 isocyanate Substances 0.000 description 1
150000002513 isocyanates Chemical class 0.000 description 1
238000002955 isolation Methods 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
229920005610 lignin Polymers 0.000 description 1
235000009973 maize Nutrition 0.000 description 1
WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical class [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
239000004579 marble Substances 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
VHCNQEUWZYOAEV-UHFFFAOYSA-N metamitron Chemical compound O=C1N(N)C(C)=NN=C1C1=CC=CC=C1 VHCNQEUWZYOAEV-UHFFFAOYSA-N 0.000 description 1
229920000609 methyl cellulose Polymers 0.000 description 1
239000001923 methylcellulose Substances 0.000 description 1
FOXFZRUHNHCZPX-UHFFFAOYSA-N metribuzin Chemical compound CSC1=NN=C(C(C)(C)C)C(=O)N1N FOXFZRUHNHCZPX-UHFFFAOYSA-N 0.000 description 1
229910052750 molybdenum Inorganic materials 0.000 description 1
239000011733 molybdenum Substances 0.000 description 1
229910052901 montmorillonite Inorganic materials 0.000 description 1
239000008164 mustard oil Substances 0.000 description 1
WLCRKQRCUPJQQY-UHFFFAOYSA-N n-[(5-bromo-1,3,4-thiadiazol-2-yl)methyl]-2,6-diethylaniline Chemical compound CCC1=CC=CC(CC)=C1NCC1=NN=C(Br)S1 WLCRKQRCUPJQQY-UHFFFAOYSA-N 0.000 description 1
UMQUHWIPSPHZPS-UHFFFAOYSA-N n-[(5-methyl-1,3,4-oxadiazol-2-yl)methyl]-2,6-di(propan-2-yl)aniline Chemical compound CC(C)C1=CC=CC(C(C)C)=C1NCC1=NN=C(C)O1 UMQUHWIPSPHZPS-UHFFFAOYSA-N 0.000 description 1
ICJAFEIQLULUGD-UHFFFAOYSA-N n-[[5-(chloromethyl)-1,3,4-oxadiazol-2-yl]methyl]-2,6-dimethylaniline Chemical compound CC1=CC=CC(C)=C1NCC1=NN=C(CCl)O1 ICJAFEIQLULUGD-UHFFFAOYSA-N 0.000 description 1
239000005645 nematicide Substances 0.000 description 1
235000014571 nuts Nutrition 0.000 description 1
239000003921 oil Substances 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
239000011368 organic material Substances 0.000 description 1
230000020477 pH reduction Effects 0.000 description 1
229910052625 palygorskite Inorganic materials 0.000 description 1
CYQAYERJWZKYML-UHFFFAOYSA-N phosphorus pentasulfide Chemical compound S1P(S2)(=S)SP3(=S)SP1(=S)SP2(=S)S3 CYQAYERJWZKYML-UHFFFAOYSA-N 0.000 description 1
239000001007 phthalocyanine dye Substances 0.000 description 1
230000008635 plant growth Effects 0.000 description 1
239000003495 polar organic solvent Substances 0.000 description 1
239000002798 polar solvent Substances 0.000 description 1
229920000642 polymer Polymers 0.000 description 1
239000011118 polyvinyl acetate Substances 0.000 description 1
229920002689 polyvinyl acetate Polymers 0.000 description 1
229920002451 polyvinyl alcohol Polymers 0.000 description 1
239000000047 product Substances 0.000 description 1
FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
239000003531 protein hydrolysate Substances 0.000 description 1
239000008262 pumice Substances 0.000 description 1
239000010453 quartz Substances 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
239000013558 reference substance Substances 0.000 description 1
239000011435 rock Substances 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
229910052624 sepiolite Inorganic materials 0.000 description 1
235000019355 sepiolite Nutrition 0.000 description 1
150000004760 silicates Chemical class 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
239000002002 slurry Substances 0.000 description 1
239000012279 sodium borohydride Substances 0.000 description 1
229910000033 sodium borohydride Inorganic materials 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
238000009331 sowing Methods 0.000 description 1
238000003892 spreading Methods 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
229940042055 systemic antimycotics triazole derivative Drugs 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
235000013616 tea Nutrition 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
ZFXYFBGIUFBOJW-UHFFFAOYSA-N theophylline Chemical compound O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 0.000 description 1
229960000278 theophylline Drugs 0.000 description 1
150000004867 thiadiazoles Chemical class 0.000 description 1
239000010936 titanium Substances 0.000 description 1
OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
235000014101 wine Nutrition 0.000 description 1
239000011701 zinc Substances 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
- 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
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
- A01N43/647—Triazoles; Hydrogenated triazoles
- A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
- 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
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/82—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with three ring hetero atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C243/00—Compounds containing chains of nitrogen atoms singly-bound to each other, e.g. hydrazines, triazanes
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
- C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
- C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D249/12—Oxygen or sulfur atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
- C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
- C07D271/10—1,3,4-Oxadiazoles; Hydrogenated 1,3,4-oxadiazoles
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
- C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
- C07D271/10—1,3,4-Oxadiazoles; Hydrogenated 1,3,4-oxadiazoles
- C07D271/113—1,3,4-Oxadiazoles; Hydrogenated 1,3,4-oxadiazoles with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/01—Five-membered rings
- C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
- C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
- C07D285/12—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/01—Five-membered rings
- C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
- C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
- C07D285/12—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles
- C07D285/125—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
Dentistry (AREA)
Wood Science & Technology (AREA)
Plant Pathology (AREA)
Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Agronomy & Crop Science (AREA)
General Health & Medical Sciences (AREA)
Pest Control & Pesticides (AREA)
Zoology (AREA)
Environmental Sciences (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Plural Heterocyclic Compounds (AREA)
Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)

DD79210848A 1978-02-10 1979-02-06 Herbizide mittel DD141899A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE19782805757 DE2805757A1 (de)	1978-02-10	1978-02-10	N-azolylalkyl-halogenacetanilide, verfahren zu ihrer herstellung sowie ihre verwendung als herbizide

Publications (1)

Publication Number	Publication Date
DD141899A5 true DD141899A5 (de)	1980-05-28

Family

ID=6031672

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD79210848A DD141899A5 (de)	1978-02-10	1979-02-06	Herbizide mittel

Country Status (18)

Country	Link
EP (1)	EP0003539B1 (fr)
JP (1)	JPS54115378A (fr)
AT (1)	AT365041B (fr)
AU (1)	AU4398479A (fr)
BG (1)	BG30313A3 (fr)
BR (1)	BR7900823A (fr)
CS (1)	CS203033B2 (fr)
DD (1)	DD141899A5 (fr)
DE (2)	DE2805757A1 (fr)
DK (1)	DK53879A (fr)
ES (1)	ES477611A1 (fr)
HU (1)	HU182925B (fr)
IL (1)	IL56614A (fr)
NZ (1)	NZ189584A (fr)
PL (1)	PL114534B1 (fr)
PT (1)	PT69183A (fr)
RO (1)	RO76593A (fr)
ZA (1)	ZA79561B (fr)

Families Citing this family (11)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4243408A (en) *	1978-05-11	1981-01-06	Chevron Research Company	Herbicidal N-triazolylmethyl-substituted alpha-haloacetanilide
US4648897A (en) *	1978-05-11	1987-03-10	Chevron Research Company	Herbicidal N-oxadiazolylmethyl-, N-thiadiazolylmethyl-, and N-triazolylmethyl-substituted alpha-haloacetanilide
DE2828222A1 (de) *	1978-06-28	1980-01-10	Bayer Ag	Gegenmittel zum schutz von kulturpflanzen vor schaedigungen durch herbizide
DE2828303A1 (de) *	1978-06-28	1980-01-17	Bayer Ag	Verwendung von n,n-diallyl-dichloracetamid zur verbesserung der kulturpflanzen- vertraeglichkeit von herbizid wirksamen acetaniliden
DE2919293A1 (de) *	1979-05-12	1980-11-20	Bayer Ag	N-(2,5-diazolyl)alkyl-halogenacetanilide, verfahren zu ihrer herstellung sowie ihre verwendung als herbizide
CA1231710A (fr) *	1979-07-19	1988-01-19	Haken Pieter Ten	Composes heterocycliques a proprietes fongicides, herbicides et regulatrices de croissance vegetale
DE3014157A1 (de) *	1980-04-12	1981-10-22	Hoechst Ag, 6000 Frankfurt	Fungizide, heterocyclisch substituierte thioglykolsaeureanilide
DE3120665A1 (de) *	1981-05-23	1982-12-16	Hoechst Ag, 6000 Frankfurt	Neue chloracetanilide, verfahren zu ihrer herstellung und sie enthaltende herbizide mittel
US4734119A (en)	1983-11-15	1988-03-29	Ciba-Geigy Corporation	Novel phosphorus compounds for protecting cultivated plants from the phytotoxic action of herbicides
EP0244948A3 (fr) *	1986-04-30	1989-03-15	Schering Agrochemicals Limited	Herbicides de triazolopyrimidine
WO2022249113A1 (fr) *	2021-05-25	2022-12-01	주식회사 자이메디	Nouveau composé inhibant la liaison entre aimp2-dx2 et kras, et son utilisation

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB1307283A (en) *	1970-03-12	1973-02-14	Takeda Chemical Industries Ltd	Herbicides
GB1551735A (en) *	1975-06-05	1979-09-12	Lilly Industries Ltd	Acylated aminothiazoles and aminooxadiazoles

1978
- 1978-02-10 DE DE19782805757 patent/DE2805757A1/de not_active Withdrawn
1979
- 1979-01-29 EP EP79100240A patent/EP0003539B1/fr not_active Expired
- 1979-01-29 DE DE7979100240T patent/DE2960238D1/de not_active Expired
- 1979-02-05 BG BG042371A patent/BG30313A3/xx unknown
- 1979-02-06 DD DD79210848A patent/DD141899A5/de unknown
- 1979-02-06 PT PT7969183A patent/PT69183A/pt unknown
- 1979-02-06 AU AU43984/79A patent/AU4398479A/en not_active Abandoned
- 1979-02-07 NZ NZ189584A patent/NZ189584A/xx unknown
- 1979-02-07 RO RO7996536A patent/RO76593A/fr unknown
- 1979-02-07 IL IL56614A patent/IL56614A/xx unknown
- 1979-02-08 CS CS79887A patent/CS203033B2/cs unknown
- 1979-02-08 JP JP1285479A patent/JPS54115378A/ja active Pending
- 1979-02-09 DK DK53879A patent/DK53879A/da not_active Application Discontinuation
- 1979-02-09 BR BR7900823A patent/BR7900823A/pt unknown
- 1979-02-09 ES ES477611A patent/ES477611A1/es not_active Expired
- 1979-02-09 AT AT0099479A patent/AT365041B/de not_active IP Right Cessation
- 1979-02-09 HU HU79BA3753A patent/HU182925B/hu unknown
- 1979-02-09 ZA ZA79561A patent/ZA79561B/xx unknown
- 1979-02-09 PL PL1979213319A patent/PL114534B1/pl unknown

Also Published As

Publication number	Publication date
ES477611A1 (es)	1979-07-16
BR7900823A (pt)	1979-09-04
ATA99479A (de)	1981-05-15
IL56614A (en)	1982-01-31
BG30313A3 (en)	1981-05-15
AT365041B (de)	1981-12-10
EP0003539A2 (fr)	1979-08-22
NZ189584A (en)	1981-02-11
JPS54115378A (en)	1979-09-07
PL114534B1 (en)	1981-02-28
EP0003539B1 (fr)	1981-04-08
EP0003539A3 (en)	1979-09-05
HU182925B (en)	1984-03-28
CS203033B2 (en)	1981-02-27
DE2805757A1 (de)	1979-08-16
IL56614A0 (en)	1979-05-31
DE2960238D1 (en)	1981-04-30
RO76593A (fr)	1981-04-30
DK53879A (da)	1979-08-11
ZA79561B (en)	1980-03-26
AU4398479A (en)	1979-08-16
PL213319A1 (fr)	1979-12-03
PT69183A (en)	1979-03-01

Publication	Publication Date	Title
EP0018497B1 (fr)	1982-04-28	Azolyloxy-acétamides, procédé pour leur préparation et leur utilisation comme herbicides
EP0029171B1 (fr)	1984-03-21	N-oxyamides dérivés des acides azolyloxycarboxyliques, procédé et intermédiaires pour leur préparation, leur utilisation, herbicides les contenant et leur préparation
EP0029183B1 (fr)	1983-01-12	Tétrazolyloxycarbonamides, procédé pour leur préparation et leur utilisation comme herbicides
EP0148501B1 (fr)	1988-05-11	5-Halogénoalkyl-1,3,4-thiadiazol-2-yloxyamides
EP0003539B1 (fr)	1981-04-08	N-Azolylalcoyl-halogénoacétanilides, leur procédé de synthèse ainsi que leur utilisation comme herbicides
DE3832348A1 (de)	1989-09-28	Substituierte benzoxazinone, mehrere verfahren sowie neue zwischenprodukte zu ihrer herstellung sowie ihre herbizide verwendung
DD144350A5 (de)	1980-10-15	Mittel zur verhuetung von herbizidschaeden an kulturpflanzen
EP0300344B1 (fr)	1993-10-06	Amides d'acides thiadiazolyloxyacétiques halogénés procédé et intermédiaires pour leur préparation et leur utilisation comme herbicides
DE2914003A1 (de)	1980-10-16	Azolyloxy-carbonsaeureamide, verfahren zu ihrer herstellung und ihre verwendung als herbizide
EP0060426B1 (fr)	1986-04-23	(2,2,2-Trifluorométhyl)-N-alkyl-azolyloxy amides de l'acide acétique, leur préparation et leur emploi comme herbicides et produits intermédiaires de préparation
DE3821597A1 (de)	1989-12-28	5-difluormethyl-1,3,4-thiadiazol-2-yl- oxyessigsaeureamide, verfahren und 5-difluormethyl-2- methylsulfonyl- bzw. 2- methylthio-1,3,4-thiadiazol als zwischenprodukte zu ihrer herstellung und ihre verwendung als selektivherbizide
EP0010163B1 (fr)	1982-01-06	N-Diazolylalcoyl-chloroacétanilides, procédé pour leur préparation et leur utilisation comme herbicides
EP0073999B1 (fr)	1986-01-15	Dérivés de pyridin-4-one substituée par un hétérocycle, procédé pour leur préparation et leur utilisation comme herbicides
US4392882A (en)	1983-07-12	N-N-Bis(haloacyl)-diaza-cycloalkanes for protecting plants from herbicide damage
EP0019742A2 (fr)	1980-12-10	N-(2,5-Diazolyl) alcoyl-halogénoacétanilides, procédés pour leur préparation et leur utilisation comme herbicides
DE2906237A1 (de)	1980-08-28	Phenoxycarbonsaeureamide, verfahren zu ihrer herstellung und ihre verwendung als herbizide
DE2805756A1 (de)	1979-08-16	N-azolylalkyl-aniline sowie verfahren zu ihrer herstellung
EP0023307A1 (fr)	1981-02-04	N-(alpha-chloropropionyl)-1,2,3,4-tétrahydroisoquinoléine, procédé pour sa préparation et son utilisation comme antidote pour la protection des plantes cultivées contre les dommages causés par les herbicides
DD149305A5 (de)	1981-07-08	Herbizide mittel
EP0337151A2 (fr)	1989-10-18	Composés phényl-hétérocycliques N-substitués
EP0006541A2 (fr)	1980-01-09	Utilisation du N,N-diallyl-dichloroacétamide pour améliorer la protection des plantes cultivées contre les herbicides à base d'acétanilides
DE4230903A1 (de)	1994-03-17	Fluorbenzthiazolyloxyacetamide
DE3821598A1 (de)	1989-12-28	5-chlor-4-cyano-thiazol-2-yl-oxyessigsaeureamide
EP0023308A1 (fr)	1981-02-04	N-acyl-pipéridonecétals, procédé pour leur préparation et leur utilisation comme antidotes pour la protection des plantes cultivées contre les dommages causés par les herbicides
DE3038635A1 (de)	1982-05-27	Substituierte 5-phenyl-1,3,4-thiadiazol-2-yl-oxyessigsaeureamide, verfahren zu ihrer herstellung und ihre verwendung als herbizide