CS203033B2 - Herbicide and process for preparing efective compound thereof - Google Patents
Herbicide and process for preparing efective compound thereof Download PDFInfo
- Publication number
- CS203033B2 CS203033B2 CS79887A CS88779A CS203033B2 CS 203033 B2 CS203033 B2 CS 203033B2 CS 79887 A CS79887 A CS 79887A CS 88779 A CS88779 A CS 88779A CS 203033 B2 CS203033 B2 CS 203033B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- ylmethyl
- carbon atoms
- methyl
- aniline
- ethyl
- Prior art date
Links
- 230000002363 herbicidal effect Effects 0.000 title claims description 7
- 150000001875 compounds Chemical class 0.000 title description 36
- 238000004519 manufacturing process Methods 0.000 title description 7
- 239000004009 herbicide Substances 0.000 title description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 82
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 40
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 33
- 125000005843 halogen group Chemical group 0.000 claims abstract description 33
- 125000001188 haloalkyl group Chemical group 0.000 claims abstract description 29
- 150000002367 halogens Chemical class 0.000 claims abstract description 23
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 16
- 239000001257 hydrogen Substances 0.000 claims abstract description 16
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 15
- 125000004414 alkyl thio group Chemical group 0.000 claims abstract description 11
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 11
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 10
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 9
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 8
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 7
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 5
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 5
- 239000001301 oxygen Substances 0.000 claims abstract description 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 4
- 239000000460 chlorine Substances 0.000 claims description 55
- 239000002253 acid Substances 0.000 claims description 19
- 229910052801 chlorine Inorganic materials 0.000 claims description 19
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 18
- 239000000203 mixture Substances 0.000 claims description 17
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 13
- 239000011737 fluorine Substances 0.000 claims description 13
- 229910052731 fluorine Inorganic materials 0.000 claims description 13
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 10
- 239000004480 active ingredient Substances 0.000 claims description 10
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 9
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 9
- 229910052794 bromium Inorganic materials 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 9
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 229910052727 yttrium Inorganic materials 0.000 claims description 7
- 239000011230 binding agent Substances 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 6
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 4
- 150000004820 halides Chemical class 0.000 claims description 4
- 239000011630 iodine Substances 0.000 claims description 4
- 229910052740 iodine Inorganic materials 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- 239000003085 diluting agent Substances 0.000 claims description 3
- 239000011593 sulfur Substances 0.000 claims description 3
- 125000001246 bromo group Chemical group Br* 0.000 claims description 2
- 125000006536 (C1-C2)alkoxy group Chemical group 0.000 claims 1
- 150000001413 amino acids Chemical class 0.000 claims 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims 1
- GBXQPDCOMJJCMJ-UHFFFAOYSA-M trimethyl-[6-(trimethylazaniumyl)hexyl]azanium;bromide Chemical compound [Br-].C[N+](C)(C)CCCCCC[N+](C)(C)C GBXQPDCOMJJCMJ-UHFFFAOYSA-M 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract description 23
- 125000003118 aryl group Chemical group 0.000 abstract description 11
- 150000002431 hydrogen Chemical class 0.000 abstract 3
- 125000006193 alkinyl group Chemical group 0.000 abstract 2
- 239000005864 Sulphur Chemical group 0.000 abstract 1
- -1 chloro, bromo, iodo Chemical group 0.000 description 114
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 70
- VONWPEXRCLHKRJ-UHFFFAOYSA-N 2-chloro-n-phenylacetamide Chemical compound ClCC(=O)NC1=CC=CC=C1 VONWPEXRCLHKRJ-UHFFFAOYSA-N 0.000 description 56
- 241000196324 Embryophyta Species 0.000 description 27
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 19
- MUUQHCOAOLLHIL-UHFFFAOYSA-N n-(3-chlorophenyl)acetamide Chemical compound CC(=O)NC1=CC=CC(Cl)=C1 MUUQHCOAOLLHIL-UHFFFAOYSA-N 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 11
- 238000005660 chlorination reaction Methods 0.000 description 11
- 239000002904 solvent Substances 0.000 description 11
- 239000013543 active substance Substances 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-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
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 239000003960 organic solvent Substances 0.000 description 9
- 239000000126 substance Substances 0.000 description 9
- 239000007858 starting material Substances 0.000 description 8
- 239000000843 powder Substances 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- 238000002844 melting Methods 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 6
- 150000008064 anhydrides Chemical class 0.000 description 5
- 239000008187 granular material Substances 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 125000000304 alkynyl group Chemical group 0.000 description 4
- 150000001805 chlorine compounds Chemical class 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 150000002429 hydrazines Chemical class 0.000 description 4
- 238000005554 pickling Methods 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
- VEUMBMHMMCOFAG-UHFFFAOYSA-N 2,3-dihydrooxadiazole Chemical compound N1NC=CO1 VEUMBMHMMCOFAG-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-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
- 235000016068 Berberis vulgaris Nutrition 0.000 description 3
- 241000335053 Beta vulgaris Species 0.000 description 3
- 241000219198 Brassica Species 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- 229920000742 Cotton Polymers 0.000 description 3
- 244000299507 Gossypium hirsutum Species 0.000 description 3
- 244000042664 Matricaria chamomilla Species 0.000 description 3
- 235000007232 Matricaria chamomilla Nutrition 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 244000062793 Sorghum vulgare Species 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 240000008042 Zea mays Species 0.000 description 3
- 235000002017 Zea mays subsp mays Nutrition 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
- 239000012141 concentrate Substances 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 239000000975 dye Substances 0.000 description 3
- 239000003995 emulsifying agent Substances 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 235000013312 flour Nutrition 0.000 description 3
- 150000002576 ketones Chemical class 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 239000002689 soil Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 125000003107 substituted aryl group Chemical group 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
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 description 2
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 description 2
- SNTWKPAKVQFCCF-UHFFFAOYSA-N 2,3-dihydro-1h-triazole Chemical compound N1NC=CN1 SNTWKPAKVQFCCF-UHFFFAOYSA-N 0.000 description 2
- KWVPRPSXBZNOHS-UHFFFAOYSA-N 2,4,6-Trimethylaniline Chemical compound CC1=CC(C)=C(N)C(C)=C1 KWVPRPSXBZNOHS-UHFFFAOYSA-N 0.000 description 2
- 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 2
- JJVKJJNCIILLRP-UHFFFAOYSA-N 2-ethyl-6-methylaniline Chemical compound CCC1=CC=CC(C)=C1N JJVKJJNCIILLRP-UHFFFAOYSA-N 0.000 description 2
- 241000219144 Abutilon Species 0.000 description 2
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- 125000000041 C6-C10 aryl group Chemical group 0.000 description 2
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- XTEGARKTQYYJKE-UHFFFAOYSA-M Chlorate Chemical compound [O-]Cl(=O)=O XTEGARKTQYYJKE-UHFFFAOYSA-M 0.000 description 2
- VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 description 2
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- UYVRIKFFSIAUST-UHFFFAOYSA-N n-[(4,5-dimethyl-1,2,4-triazol-3-yl)methyl]-2-ethyl-6-methylaniline Chemical compound CCC1=CC=CC(C)=C1NCC1=NN=C(C)N1C UYVRIKFFSIAUST-UHFFFAOYSA-N 0.000 description 1
- HVALSLDPPHVUFW-UHFFFAOYSA-N n-[(5-benzyl-1,3,4-oxadiazol-2-yl)methyl]-2-ethyl-6-methylaniline Chemical compound CCC1=CC=CC(C)=C1NCC(O1)=NN=C1CC1=CC=CC=C1 HVALSLDPPHVUFW-UHFFFAOYSA-N 0.000 description 1
- WLPOSDPPSDNBQV-UHFFFAOYSA-N n-[(5-bromo-1,3,4-oxadiazol-2-yl)methyl]-2,6-diethylaniline Chemical compound CCC1=CC=CC(CC)=C1NCC1=NN=C(Br)O1 WLPOSDPPSDNBQV-UHFFFAOYSA-N 0.000 description 1
- OBLXPGOUUQGZLZ-UHFFFAOYSA-N n-[(5-bromo-1,3,4-oxadiazol-2-yl)methyl]-2-ethyl-6-methylaniline Chemical compound CCC1=CC=CC(C)=C1NCC1=NN=C(Br)O1 OBLXPGOUUQGZLZ-UHFFFAOYSA-N 0.000 description 1
- MQXPFUSTFKJCBP-UHFFFAOYSA-N n-[(5-chloro-1,3,4-oxadiazol-2-yl)methyl]-2,6-diethylaniline Chemical compound CCC1=CC=CC(CC)=C1NCC1=NN=C(Cl)O1 MQXPFUSTFKJCBP-UHFFFAOYSA-N 0.000 description 1
- XPVHMSMFXPBIAT-UHFFFAOYSA-N n-[(5-chloro-1,3,4-oxadiazol-2-yl)methyl]-2,6-dimethylaniline Chemical compound CC1=CC=CC(C)=C1NCC1=NN=C(Cl)O1 XPVHMSMFXPBIAT-UHFFFAOYSA-N 0.000 description 1
- XWOWSRACSCQTMI-UHFFFAOYSA-N n-[(5-chloro-1,3,4-oxadiazol-2-yl)methyl]-2-ethyl-6-methylaniline Chemical compound CCC1=CC=CC(C)=C1NCC1=NN=C(Cl)O1 XWOWSRACSCQTMI-UHFFFAOYSA-N 0.000 description 1
- BVFJFCPXQHJQCU-UHFFFAOYSA-N n-[(5-ethyl-1,3,4-oxadiazol-2-yl)methyl]-2,6-dimethylaniline Chemical compound O1C(CC)=NN=C1CNC1=C(C)C=CC=C1C BVFJFCPXQHJQCU-UHFFFAOYSA-N 0.000 description 1
- LGSKAUNJPCGURT-UHFFFAOYSA-N n-[(5-ethyl-1,3,4-thiadiazol-2-yl)methyl]-2,6-dimethylaniline Chemical compound S1C(CC)=NN=C1CNC1=C(C)C=CC=C1C LGSKAUNJPCGURT-UHFFFAOYSA-N 0.000 description 1
- LRNSMYLTISXEOX-UHFFFAOYSA-N n-[(5-ethyl-4-methyl-1,2,4-triazol-3-yl)methyl]-2,6-dimethylaniline Chemical compound CN1C(CC)=NN=C1CNC1=C(C)C=CC=C1C LRNSMYLTISXEOX-UHFFFAOYSA-N 0.000 description 1
- ODAZEKLLUICZCU-UHFFFAOYSA-N n-[(5-ethylsulfanyl-1,3,4-thiadiazol-2-yl)methyl]-2,6-dimethylaniline Chemical compound S1C(SCC)=NN=C1CNC1=C(C)C=CC=C1C ODAZEKLLUICZCU-UHFFFAOYSA-N 0.000 description 1
- SSKRTAYQBNFCAR-UHFFFAOYSA-N n-[(5-methoxy-1,3,4-oxadiazol-2-yl)methyl]-2,6-dimethylaniline Chemical compound O1C(OC)=NN=C1CNC1=C(C)C=CC=C1C SSKRTAYQBNFCAR-UHFFFAOYSA-N 0.000 description 1
- UJIIDHMYVYWMDZ-UHFFFAOYSA-N n-[(5-methoxy-4-methyl-1,2,4-triazol-3-yl)methyl]-2,6-dimethylaniline Chemical compound CN1C(OC)=NN=C1CNC1=C(C)C=CC=C1C UJIIDHMYVYWMDZ-UHFFFAOYSA-N 0.000 description 1
- OEGYPLZYRGCFHX-UHFFFAOYSA-N n-[(5-methoxy-4-phenyl-1,2,4-triazol-3-yl)methyl]-2,6-dimethylaniline Chemical compound C=1C=CC=CC=1N1C(OC)=NN=C1CNC1=C(C)C=CC=C1C OEGYPLZYRGCFHX-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
- YUUDYCWWAVHICM-UHFFFAOYSA-N n-[(5-methyl-1,3,4-thiadiazol-2-yl)methyl]-2-propan-2-ylaniline Chemical compound CC(C)C1=CC=CC=C1NCC1=NN=C(C)S1 YUUDYCWWAVHICM-UHFFFAOYSA-N 0.000 description 1
- ZHIMRZOEFUBEHJ-UHFFFAOYSA-N n-[[5-(chloromethyl)-1,3,4-oxadiazol-2-yl]methyl]-2,6-diethylaniline Chemical compound CCC1=CC=CC(CC)=C1NCC1=NN=C(CCl)O1 ZHIMRZOEFUBEHJ-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
- RFWKFZZCRWXENW-UHFFFAOYSA-N n-[[5-(chloromethyl)-1,3,4-oxadiazol-2-yl]methyl]-2-ethyl-6-methylaniline Chemical compound CCC1=CC=CC(C)=C1NCC1=NN=C(CCl)O1 RFWKFZZCRWXENW-UHFFFAOYSA-N 0.000 description 1
- 230000001069 nematicidal effect Effects 0.000 description 1
- 239000005645 nematicide Substances 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 229940045681 other alkylating agent in atc Drugs 0.000 description 1
- 229910052625 palygorskite Inorganic materials 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 235000020232 peanut Nutrition 0.000 description 1
- 238000003408 phase transfer catalysis Methods 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
- 239000003495 polar organic solvent Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920000056 polyoxyethylene ether Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 235000012015 potatoes Nutrition 0.000 description 1
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
- ZSKGQVFRTSEPJT-UHFFFAOYSA-N pyrrole-2-carboxaldehyde Chemical class O=CC1=CC=CN1 ZSKGQVFRTSEPJT-UHFFFAOYSA-N 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 239000000377 silicon dioxide 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
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 238000009331 sowing Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 235000013616 tea Nutrition 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 229960002180 tetracycline Drugs 0.000 description 1
- 229930101283 tetracycline Natural products 0.000 description 1
- 235000019364 tetracycline Nutrition 0.000 description 1
- 150000003522 tetracyclines 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
- 239000004408 titanium dioxide Substances 0.000 description 1
- 239000011573 trace mineral Substances 0.000 description 1
- 235000013619 trace mineral Nutrition 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 239000002699 waste material Substances 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)
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 |
|---|---|
| CS203033B2 true CS203033B2 (en) | 1981-02-27 |
Family
ID=6031672
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS79887A CS203033B2 (en) | 1978-02-10 | 1979-02-08 | Herbicide and process for preparing efective compound thereof |
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)
| 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 |
| 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 |
| DE2828222A1 (de) * | 1978-06-28 | 1980-01-10 | Bayer Ag | Gegenmittel zum schutz von kulturpflanzen vor schaedigungen durch herbizide |
| 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)
| 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 AU AU43984/79A patent/AU4398479A/en not_active Abandoned
- 1979-02-06 PT PT7969183A patent/PT69183A/pt unknown
- 1979-02-06 DD DD79210848A patent/DD141899A5/de unknown
- 1979-02-07 NZ NZ189584A patent/NZ189584A/xx unknown
- 1979-02-07 IL IL56614A patent/IL56614A/xx unknown
- 1979-02-07 RO RO7996536A patent/RO76593A/fr unknown
- 1979-02-08 CS CS79887A patent/CS203033B2/cs unknown
- 1979-02-08 JP JP1285479A patent/JPS54115378A/ja active Pending
- 1979-02-09 HU HU79BA3753A patent/HU182925B/hu unknown
- 1979-02-09 PL PL1979213319A patent/PL114534B1/pl 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 ZA ZA79561A patent/ZA79561B/xx unknown
- 1979-02-09 BR BR7900823A patent/BR7900823A/pt unknown
- 1979-02-09 DK DK53879A patent/DK53879A/da not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| BR7900823A (pt) | 1979-09-04 |
| DE2960238D1 (en) | 1981-04-30 |
| RO76593A (fr) | 1981-04-30 |
| DD141899A5 (de) | 1980-05-28 |
| PL114534B1 (en) | 1981-02-28 |
| AU4398479A (en) | 1979-08-16 |
| EP0003539A3 (en) | 1979-09-05 |
| JPS54115378A (en) | 1979-09-07 |
| ES477611A1 (es) | 1979-07-16 |
| AT365041B (de) | 1981-12-10 |
| HU182925B (en) | 1984-03-28 |
| BG30313A3 (en) | 1981-05-15 |
| IL56614A (en) | 1982-01-31 |
| DK53879A (da) | 1979-08-11 |
| DE2805757A1 (de) | 1979-08-16 |
| EP0003539A2 (fr) | 1979-08-22 |
| IL56614A0 (en) | 1979-05-31 |
| NZ189584A (en) | 1981-02-11 |
| ZA79561B (en) | 1980-03-26 |
| EP0003539B1 (fr) | 1981-04-08 |
| PL213319A1 (fr) | 1979-12-03 |
| PT69183A (en) | 1979-03-01 |
| ATA99479A (de) | 1981-05-15 |
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| PL69564B1 (fr) |