DD200969A5 - Herbizide mittel - Google Patents
Herbizide mittel Download PDFInfo
- Publication number
- DD200969A5 DD200969A5 DD81235017A DD23501781A DD200969A5 DD 200969 A5 DD200969 A5 DD 200969A5 DD 81235017 A DD81235017 A DD 81235017A DD 23501781 A DD23501781 A DD 23501781A DD 200969 A5 DD200969 A5 DD 200969A5
- Authority
- DD
- German Democratic Republic
- Prior art keywords
- atom
- fluorine
- group
- hydrogen
- nicotinamide
- Prior art date
Links
- 230000002363 herbicidal effect Effects 0.000 title claims abstract description 26
- 239000004009 herbicide Substances 0.000 title claims description 16
- -1 phenoxynicotinic acid halide Chemical class 0.000 claims abstract description 106
- 239000000203 mixture Substances 0.000 claims abstract description 75
- 239000004480 active ingredient Substances 0.000 claims abstract description 14
- 150000005480 nicotinamides Chemical class 0.000 claims abstract description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 47
- 229910052731 fluorine Inorganic materials 0.000 claims description 43
- 125000001153 fluoro group Chemical group F* 0.000 claims description 32
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 27
- 229910052801 chlorine Chemical group 0.000 claims description 22
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 22
- 239000011737 fluorine Chemical group 0.000 claims description 19
- 239000001257 hydrogen Substances 0.000 claims description 18
- 229910052739 hydrogen Inorganic materials 0.000 claims description 18
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 17
- 239000003085 diluting agent Substances 0.000 claims description 17
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 14
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 14
- 239000004094 surface-active agent Substances 0.000 claims description 13
- 239000004563 wettable powder Substances 0.000 claims description 13
- 239000013543 active substance Substances 0.000 claims description 11
- 239000008187 granular material Substances 0.000 claims description 11
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 11
- 239000000460 chlorine Substances 0.000 claims description 10
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 8
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 8
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 150000001335 aliphatic alkanes Chemical group 0.000 claims description 4
- 239000007900 aqueous suspension Substances 0.000 claims description 4
- 125000004429 atom Chemical group 0.000 claims description 4
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 4
- 229910052717 sulfur Chemical group 0.000 claims description 4
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 3
- 125000004434 sulfur atom Chemical group 0.000 claims description 3
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 3
- 239000000839 emulsion Substances 0.000 claims description 2
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 239000002152 aqueous-organic solution Substances 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 91
- 241000196324 Embryophyta Species 0.000 abstract description 63
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- CYQAYERJWZKYML-UHFFFAOYSA-N phosphorus pentasulfide Chemical compound S1P(S2)(=S)SP3(=S)SP1(=S)SP2(=S)S3 CYQAYERJWZKYML-UHFFFAOYSA-N 0.000 abstract description 4
- 150000008064 anhydrides Chemical class 0.000 abstract description 3
- 150000001447 alkali salts Chemical class 0.000 abstract description 2
- 150000002989 phenols Chemical class 0.000 abstract description 2
- XQWBMZWDJAZPPX-UHFFFAOYSA-N pyridine-3-carbothioamide Chemical class NC(=S)C1=CC=CN=C1 XQWBMZWDJAZPPX-UHFFFAOYSA-N 0.000 abstract description 2
- 125000002490 anilino group Chemical class [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 abstract 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 126
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 75
- 238000001953 recrystallisation Methods 0.000 description 55
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 37
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 30
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 30
- 230000012010 growth Effects 0.000 description 27
- 239000000243 solution Substances 0.000 description 26
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 24
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- DFPAKSUCGFBDDF-ZQBYOMGUSA-N [14c]-nicotinamide Chemical compound N[14C](=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-ZQBYOMGUSA-N 0.000 description 21
- 239000007787 solid Substances 0.000 description 20
- 239000007788 liquid Substances 0.000 description 19
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 19
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 16
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
- 238000000034 method Methods 0.000 description 14
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 13
- 229910052757 nitrogen Inorganic materials 0.000 description 12
- 238000005507 spraying Methods 0.000 description 12
- 125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 description 11
- 240000006694 Stellaria media Species 0.000 description 11
- 239000002253 acid Substances 0.000 description 11
- 239000000843 powder Substances 0.000 description 11
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 10
- QFMDFTQOJHFVNR-UHFFFAOYSA-N 1-[2,2-dichloro-1-(4-ethylphenyl)ethyl]-4-ethylbenzene Chemical compound C1=CC(CC)=CC=C1C(C(Cl)Cl)C1=CC=C(CC)C=C1 QFMDFTQOJHFVNR-UHFFFAOYSA-N 0.000 description 9
- DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical class NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 235000021307 Triticum Nutrition 0.000 description 9
- 244000098338 Triticum aestivum Species 0.000 description 9
- 241000990144 Veronica persica Species 0.000 description 9
- 239000002689 soil Substances 0.000 description 9
- 238000003756 stirring Methods 0.000 description 9
- 235000014820 Galium aparine Nutrition 0.000 description 8
- 240000005702 Galium aparine Species 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- 239000000969 carrier Substances 0.000 description 8
- 239000012141 concentrate Substances 0.000 description 8
- 235000008504 concentrate Nutrition 0.000 description 8
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 8
- 239000011664 nicotinic acid Substances 0.000 description 8
- 229960003512 nicotinic acid Drugs 0.000 description 8
- 239000003921 oil Substances 0.000 description 8
- 235000019198 oils Nutrition 0.000 description 8
- RZXMPPFPUUCRFN-UHFFFAOYSA-N p-toluidine Chemical compound CC1=CC=C(N)C=C1 RZXMPPFPUUCRFN-UHFFFAOYSA-N 0.000 description 8
- 150000003839 salts Chemical class 0.000 description 8
- 239000007921 spray Substances 0.000 description 8
- OBRGOFGSXWAVNZ-UHFFFAOYSA-N 2-[3-(trifluoromethyl)phenoxy]pyridine-3-carboxylic acid Chemical compound OC(=O)C1=CC=CN=C1OC1=CC=CC(C(F)(F)F)=C1 OBRGOFGSXWAVNZ-UHFFFAOYSA-N 0.000 description 7
- KRZCOLNOCZKSDF-UHFFFAOYSA-N 4-fluoroaniline Chemical compound NC1=CC=C(F)C=C1 KRZCOLNOCZKSDF-UHFFFAOYSA-N 0.000 description 7
- 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 7
- 238000002360 preparation method Methods 0.000 description 7
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- 150000001408 amides Chemical class 0.000 description 6
- 238000000227 grinding Methods 0.000 description 6
- 238000010438 heat treatment Methods 0.000 description 6
- AXURHPCMXFGUFF-UHFFFAOYSA-N n-(4-fluorophenyl)-2-[3-(trifluoromethyl)phenoxy]pyridine-3-carboxamide Chemical compound C1=CC(F)=CC=C1NC(=O)C1=CC=CN=C1OC1=CC=CC(C(F)(F)F)=C1 AXURHPCMXFGUFF-UHFFFAOYSA-N 0.000 description 6
- 235000001968 nicotinic acid Nutrition 0.000 description 6
- 239000003960 organic solvent Substances 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- CEPCPXLLFXPZGW-UHFFFAOYSA-N 2,4-difluoroaniline Chemical compound NC1=CC=C(F)C=C1F CEPCPXLLFXPZGW-UHFFFAOYSA-N 0.000 description 5
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- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 5
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- 239000004615 ingredient Substances 0.000 description 5
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- BJSVKBGQDHUBHZ-UHFFFAOYSA-N 2,4,6-trifluoroaniline Chemical compound NC1=C(F)C=C(F)C=C1F BJSVKBGQDHUBHZ-UHFFFAOYSA-N 0.000 description 4
- IBRSSZOHCGUTHI-UHFFFAOYSA-N 2-chloropyridine-3-carboxylic acid Chemical compound OC(=O)C1=CC=CN=C1Cl IBRSSZOHCGUTHI-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
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- 125000000217 alkyl group Chemical group 0.000 description 4
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- MRUHQAYQFHBAOT-UHFFFAOYSA-N 2-(3-methylsulfonylphenoxy)pyridine-3-carboxylic acid Chemical compound CS(=O)(=O)C1=CC=CC(OC=2C(=CC=CN=2)C(O)=O)=C1 MRUHQAYQFHBAOT-UHFFFAOYSA-N 0.000 description 3
- YSEMCVGMNUUNRK-UHFFFAOYSA-N 3-chloro-4-fluoroaniline Chemical compound NC1=CC=C(F)C(Cl)=C1 YSEMCVGMNUUNRK-UHFFFAOYSA-N 0.000 description 3
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- 229910000391 tricalcium phosphate Inorganic materials 0.000 description 1
- 235000019731 tricalcium phosphate Nutrition 0.000 description 1
- ZSDSQXJSNMTJDA-UHFFFAOYSA-N trifluralin Chemical compound CCCN(CCC)C1=C([N+]([O-])=O)C=C(C(F)(F)F)C=C1[N+]([O-])=O ZSDSQXJSNMTJDA-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 229920001285 xanthan gum Polymers 0.000 description 1
- 239000008096 xylene Substances 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
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/79—Acids; Esters
- C07D213/80—Acids; Esters in position 3
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/81—Amides; Imides
- C07D213/82—Amides; Imides in position 3
-
- 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
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/83—Thioacids; Thioesters; Thioamides; Thioimides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Pyridine Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB8037372 | 1980-11-21 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DD200969A5 true DD200969A5 (de) | 1983-06-29 |
Family
ID=10517468
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD81235017A DD200969A5 (de) | 1980-11-21 | 1981-11-20 | Herbizide mittel |
Country Status (34)
| Country | Link |
|---|---|
| US (1) | US4618366A (OSRAM) |
| EP (1) | EP0053011B1 (OSRAM) |
| JP (1) | JPS57118568A (OSRAM) |
| KR (1) | KR880001314B1 (OSRAM) |
| AR (1) | AR229801A1 (OSRAM) |
| AT (1) | ATE12491T1 (OSRAM) |
| AU (1) | AU557053B2 (OSRAM) |
| BG (1) | BG47942A3 (OSRAM) |
| BR (1) | BR8107585A (OSRAM) |
| CA (1) | CA1229612A (OSRAM) |
| CS (1) | CS228525B2 (OSRAM) |
| DD (1) | DD200969A5 (OSRAM) |
| DE (1) | DE3169738D1 (OSRAM) |
| DK (1) | DK171022B1 (OSRAM) |
| EG (1) | EG15683A (OSRAM) |
| ES (3) | ES8401468A1 (OSRAM) |
| GB (1) | GB2087887B (OSRAM) |
| GR (1) | GR77297B (OSRAM) |
| HU (1) | HU188711B (OSRAM) |
| IE (1) | IE52802B1 (OSRAM) |
| IL (1) | IL64220A (OSRAM) |
| KE (1) | KE3798A (OSRAM) |
| MA (1) | MA19337A1 (OSRAM) |
| MY (1) | MY8700515A (OSRAM) |
| NZ (1) | NZ199006A (OSRAM) |
| OA (1) | OA06956A (OSRAM) |
| PH (1) | PH18472A (OSRAM) |
| PL (1) | PL132171B1 (OSRAM) |
| PT (1) | PT74020B (OSRAM) |
| RO (3) | RO87037B (OSRAM) |
| SG (1) | SG8688G (OSRAM) |
| SU (1) | SU1356950A3 (OSRAM) |
| TR (1) | TR22684A (OSRAM) |
| ZA (1) | ZA818032B (OSRAM) |
Families Citing this family (59)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4744819A (en) * | 1984-10-23 | 1988-05-17 | Daicel Chemical Industries Ltd. | 4-oxo pyridinecarboxamide derivatives as plant growth regulators |
| US4725306A (en) * | 1984-11-09 | 1988-02-16 | Daicel Chemical Industries Ltd. | Pyridinecarboxamide plant growth inhibitors |
| GR861640B (en) * | 1985-07-02 | 1986-10-24 | May & Baker Ltd | Insecticide method by using diflufenican |
| CA1282975C (en) * | 1985-07-23 | 1991-04-16 | Richard Henry Hewett | Herbicidal method comprising the use of diflufenican |
| US5264411A (en) * | 1985-07-23 | 1993-11-23 | May & Baker Limited | Herbicidal method comprising the use of diflufenican |
| GB8526735D0 (en) * | 1985-10-30 | 1985-12-04 | May & Baker Ltd | Compositions of matter |
| US4692185A (en) * | 1986-01-13 | 1987-09-08 | Stauffer Chemical Company | N-(ortho-substituted) benzyl, 3-trifluoromethylphenoxy nicotinamides as herbicides |
| GB8617740D0 (en) * | 1986-07-21 | 1986-08-28 | May & Baker Ltd | Compositions of matter |
| GB8617741D0 (en) * | 1986-07-21 | 1986-08-28 | May & Baker Ltd | Compositions of matter |
| GB8630697D0 (en) * | 1986-12-23 | 1987-02-04 | May & Baker Ltd | Compositions of matter |
| GB8630698D0 (en) * | 1986-12-23 | 1987-02-04 | May & Baker Ltd | Compositions of matter |
| GB8630806D0 (en) * | 1986-12-23 | 1987-02-04 | May & Baker Ltd | Compositions of matter |
| GB8710362D0 (en) * | 1987-05-01 | 1987-06-03 | Shell Int Research | Anilide herbicides |
| GB8710585D0 (en) * | 1987-05-05 | 1987-06-10 | May & Baker Ltd | Compositions of matter |
| GB8710584D0 (en) * | 1987-05-05 | 1987-06-10 | May & Baker Ltd | Compositions of matter |
| US4861891A (en) * | 1988-08-31 | 1989-08-29 | Pfizer Inc. | Antidepressant N-substituted nicotinamide compounds |
| FR2639185B1 (fr) * | 1988-11-22 | 1991-01-25 | Rhone Poulenc Agrochimie | Produit herbicide, son utilisation et procede pour la lutte selective contre les mauvaises herbes dans les cultures de riz et de cereales |
| DE4021439A1 (de) * | 1989-12-14 | 1991-06-20 | Bayer Ag | 2-iminopyridin-derivate |
| GB9005965D0 (en) * | 1990-03-16 | 1990-05-09 | Shell Int Research | Herbicidal carboxamide derivatives |
| GB9025828D0 (en) * | 1990-11-28 | 1991-01-09 | Shell Int Research | Herbicidal carboxamide derivatives |
| TR25135A (tr) * | 1991-03-13 | 1992-11-01 | Shell Int Research | HERBISID ÖZELLIKTE KARBOKSAMID TüREVLERI |
| IL109104A (en) * | 1993-03-26 | 1998-08-16 | Shell Int Research | History of pyridine from wool - 2,6 Preparation and use as herbicides containing them |
| WO1997024329A1 (fr) | 1995-12-28 | 1997-07-10 | Kureha Kagaku Kogyo Kabushiki Kaisha | Procede de production de pyridinecarboxamides ou de thiocarboxamides |
| ES2212005T3 (es) * | 1996-03-21 | 2004-07-16 | Lonza Ag | Procedimiento para preparar arilamidas de acidos carboxilicos heteroaromaticos. |
| SK283920B6 (sk) | 1996-03-28 | 2004-05-04 | Lonza Ag | Spôsob výroby arylamidov heteroaromatických karboxylových kyselín |
| ATE189815T1 (de) * | 1996-05-09 | 2000-03-15 | Lonza Ag | Verfahren zur herstellung von arylamiden heteroaromatischer carbonsäuren |
| US5900484A (en) * | 1996-09-18 | 1999-05-04 | Lonza Ag | Process for the preparation of arylamides of heteroaromatic carboxylic acids |
| CA2209392C (en) * | 1996-07-23 | 2007-02-20 | Yves Bessard | Process for preparing pyridinecarboxylic esters |
| EA003528B1 (ru) * | 1997-04-04 | 2003-06-26 | Пфайзер Продактс Инк. | Производные никотинамида, их применение, фармацевтическая композиция, способ лечения и способ ингибирования изоферментов фдэ4 d |
| DE19854081A1 (de) * | 1998-11-24 | 2000-05-25 | Bayer Ag | Substituierte N-Pyrazolyl-phenoxynicotinsäure-(thio)amide |
| DE19946852A1 (de) * | 1999-09-30 | 2001-04-05 | Bayer Ag | Substituierte N-Phenyl-phenoxynicotinsäure-(thio)amide |
| KR100661081B1 (ko) * | 2000-06-10 | 2006-12-26 | 동화약품공업주식회사 | 항바이러스제로 유용한 6-메틸니코틴아미드 유도체 |
| BRPI0209726B1 (pt) * | 2001-05-31 | 2015-06-30 | Nihon Nohyaku Co Ltd | Derivado de anilida substituída, produto químico agrícola e hortícola, e, método para aplicar o mesmo |
| DE102004047927A1 (de) * | 2004-10-01 | 2006-04-06 | Bayer Cropscience Gmbh | Wässrige Dispersionen enthaltend Diflufenican |
| AU2006200731B2 (en) | 2005-03-31 | 2011-05-19 | Sumitomo Chemical Company, Limited | Emulsifiable concentrate |
| JP4862989B2 (ja) * | 2006-03-09 | 2012-01-25 | 日産化学工業株式会社 | 除草剤組成物 |
| EP2052606A1 (de) | 2007-10-24 | 2009-04-29 | Bayer CropScience AG | Herbizid-Kombination |
| DE102008037620A1 (de) | 2008-08-14 | 2010-02-18 | Bayer Crop Science Ag | Herbizid-Kombination mit Dimethoxytriazinyl-substituierten Difluormethansulfonylaniliden |
| PE20110574A1 (es) * | 2008-10-29 | 2011-08-11 | Hoffmann La Roche | Derivados de fenilamida y de piridilamida como agonistas de gpbar1 |
| PT3284346T (pt) | 2010-10-15 | 2021-09-29 | Bayer Cropscience Ag | Utilização de herbicidas inibidores de als para controlo de vegetação indesejada em plantas de beta vulgaris tolerantes a inibidor de als |
| EP2713733B1 (en) | 2011-05-04 | 2018-03-14 | Bayer Intellectual Property GmbH | Use of als inhibitor herbicides for control of unwanted vegetation in als inhibitor herbicide tolerant brassica, such as b. napus, plants |
| CN102318608A (zh) * | 2011-07-06 | 2012-01-18 | 陕西美邦农药有限公司 | 一种含吡氟酰草胺与吡草醚的除草组合物 |
| CN105377028B (zh) | 2012-12-13 | 2018-11-30 | 拜耳作物科学股份公司 | Als抑制剂除草剂用于在对als抑制剂除草剂耐受的甜菜植物中防治不想要的植物的用途 |
| CN105164112B (zh) * | 2013-01-31 | 2017-10-13 | 中国科学院上海药物研究所 | 酰胺类化合物及其制备方法、药物组合物和用途 |
| CN103947666A (zh) * | 2014-03-21 | 2014-07-30 | 江苏省农业科学院 | 一种含绿麦隆、丙草胺和吡氟酰草胺的农药组合物及其应用 |
| CN104402814A (zh) * | 2014-12-01 | 2015-03-11 | 南通嘉禾化工有限公司 | 一锅法合成2-氯-n-(2,4-二氟苯基)烟酰胺的方法 |
| LT3270695T (lt) * | 2015-03-20 | 2019-03-25 | Bayer Cropscience Aktiengesellschaft | Herbicidinės kompozicijos, turinčios izoksaflutolį ir diflufenikaną kaip vienintelius veikliuosius herbicidinius ingredientus |
| WO2016173964A1 (en) | 2015-04-27 | 2016-11-03 | Bayer Cropscience Aktiengesellschaft | Use of certain herbicide combinations in tuberous root crop plants |
| CN107743360A (zh) | 2015-04-27 | 2018-02-27 | 拜耳作物科学股份公司 | 某些除草剂结合物在块根作物植物中的用途 |
| PT108561B (pt) | 2015-06-16 | 2017-07-20 | Sapec Agro S A | Mistura herbicida |
| CN113615697A (zh) | 2015-10-22 | 2021-11-09 | 阿达玛阿甘有限公司 | 用于马铃薯的除草剂混合物及制剂 |
| CN112689633B (zh) * | 2018-07-09 | 2025-01-24 | 利伯研究所公司 | 用于抑制Nav1.8的吡啶甲酰胺化合物 |
| CA3203568A1 (en) | 2020-12-01 | 2022-06-09 | Bayer Aktiengesellschaft | Compositions comprising mesosulfuron-methyl and tehp |
| WO2022117515A1 (en) | 2020-12-01 | 2022-06-09 | Bayer Aktiengesellschaft | Compositions comprising iodosulfuron-methyl and tehp |
| CN113666868A (zh) * | 2021-08-11 | 2021-11-19 | 池州飞昊达化工有限公司 | 一种氟吡啶酰胺衍生物及其合成方法 |
| GB2611348A (en) * | 2021-10-01 | 2023-04-05 | Rotam Agrochem Int Co Ltd | A crystalline form of diflufenican, a process for its preparation and use of the same |
| JP2024537389A (ja) | 2021-10-15 | 2024-10-10 | カー・ヴェー・エス ザート エス・エー ウント コー． カー・ゲー・アー・アー | Ａｌｓ阻害剤除草剤耐性ベータ・ブルガリス（ｂｅｔａ ｖｕｌｇａｒｉｓ）突然変異体 |
| AU2023314958A1 (en) | 2022-07-25 | 2025-03-13 | Syngenta Crop Protection Ag | Herbicidal compositions |
| AU2023363856A1 (en) * | 2022-10-18 | 2025-04-17 | Upl Europe Supply Chain Gmbh | A method of controlling weeds |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2197872A1 (en) * | 1972-09-04 | 1974-03-29 | Dynachim Sarl | 2-Phenoxy nicotinic esters and amides - prepd. by reaction of nicotinic acid anhydride or halide with an alcohol or amine |
| GB1550574A (en) * | 1977-12-12 | 1979-08-15 | Ciba Geigy Ag | Pyridyloxy-phenoxy-propionic acid derivatives which are effective as herbicides and as agents regulating plant growth |
| US4270946A (en) * | 1979-10-01 | 1981-06-02 | Stauffer Chemical Company | N-Aryl,2-phenoxy nicotinamide compounds and the herbicidal use thereof |
| US4327218A (en) * | 1979-10-01 | 1982-04-27 | Stauffer Chemical Company | N-Aryl, 2-phenoxy nicotinamide compounds and the herbicidal use thereof |
-
1981
- 1981-11-05 IL IL64220A patent/IL64220A/xx not_active IP Right Cessation
- 1981-11-18 RO RO112516A patent/RO87037B/ro unknown
- 1981-11-18 RO RO105810A patent/RO83101B/ro unknown
- 1981-11-18 RO RO112517A patent/RO87038B/ro unknown
- 1981-11-19 AU AU77632/81A patent/AU557053B2/en not_active Expired
- 1981-11-19 DK DK513481A patent/DK171022B1/da not_active IP Right Cessation
- 1981-11-19 AT AT81305475T patent/ATE12491T1/de not_active IP Right Cessation
- 1981-11-19 GB GB8134876A patent/GB2087887B/en not_active Expired
- 1981-11-19 BG BG054211A patent/BG47942A3/xx unknown
- 1981-11-19 EP EP81305475A patent/EP0053011B1/en not_active Expired
- 1981-11-19 IE IE2713/81A patent/IE52802B1/en not_active IP Right Cessation
- 1981-11-19 NZ NZ199006A patent/NZ199006A/en unknown
- 1981-11-19 ZA ZA818032A patent/ZA818032B/xx unknown
- 1981-11-19 CA CA000390462A patent/CA1229612A/en not_active Expired
- 1981-11-19 PH PH26522A patent/PH18472A/en unknown
- 1981-11-19 PL PL1981233901A patent/PL132171B1/pl unknown
- 1981-11-19 JP JP56186089A patent/JPS57118568A/ja active Granted
- 1981-11-19 DE DE8181305475T patent/DE3169738D1/de not_active Expired
- 1981-11-20 AR AR287523A patent/AR229801A1/es active
- 1981-11-20 DD DD81235017A patent/DD200969A5/de not_active IP Right Cessation
- 1981-11-20 BR BRPI8107585-5A patent/BR8107585A/pt not_active IP Right Cessation
- 1981-11-20 PT PT74020A patent/PT74020B/pt unknown
- 1981-11-20 CS CS818553A patent/CS228525B2/cs unknown
- 1981-11-20 HU HU813480A patent/HU188711B/hu unknown
- 1981-11-20 KR KR1019810004489A patent/KR880001314B1/ko not_active Expired
- 1981-11-20 SU SU813424175A patent/SU1356950A3/ru active
- 1981-11-20 ES ES507332A patent/ES8401468A1/es not_active Expired
- 1981-11-20 GR GR66584A patent/GR77297B/el unknown
- 1981-11-20 MA MA19541A patent/MA19337A1/fr unknown
- 1981-11-20 TR TR7731/81A patent/TR22684A/xx unknown
- 1981-11-21 EG EG680/81A patent/EG15683A/xx active
- 1981-11-21 OA OA57552A patent/OA06956A/xx unknown
-
1982
- 1982-09-28 ES ES515995A patent/ES8400737A1/es not_active Expired
-
1983
- 1983-02-25 ES ES520104A patent/ES520104A0/es active Granted
-
1984
- 1984-06-15 US US06/621,102 patent/US4618366A/en not_active Expired - Lifetime
-
1987
- 1987-12-30 MY MY515/87A patent/MY8700515A/xx unknown
-
1988
- 1988-02-05 SG SG86/88A patent/SG8688G/en unknown
- 1988-02-19 KE KE3798A patent/KE3798A/xx unknown
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