ZA200600691B - N-'2-(2-pyridinyl) ethylbenzamide compounds and their use as fungicides - Google Patents
N-'2-(2-pyridinyl) ethylbenzamide compounds and their use as fungicides Download PDFInfo
- Publication number
- ZA200600691B ZA200600691B ZA200600691A ZA200600691A ZA200600691B ZA 200600691 B ZA200600691 B ZA 200600691B ZA 200600691 A ZA200600691 A ZA 200600691A ZA 200600691 A ZA200600691 A ZA 200600691A ZA 200600691 B ZA200600691 B ZA 200600691B
- Authority
- ZA
- South Africa
- Prior art keywords
- group
- general formula
- alkyl
- compound
- halogen atoms
- Prior art date
Links
- 239000000417 fungicide Substances 0.000 title description 2
- GKTFLKJXZOYBRW-UHFFFAOYSA-N 2-ethylbenzamide Chemical class CCC1=CC=CC=C1C(N)=O GKTFLKJXZOYBRW-UHFFFAOYSA-N 0.000 title 1
- 125000005843 halogen group Chemical group 0.000 claims description 142
- 150000001875 compounds Chemical class 0.000 claims description 121
- 125000000217 alkyl group Chemical group 0.000 claims description 60
- 125000001188 haloalkyl group Chemical group 0.000 claims description 58
- 238000000034 method Methods 0.000 claims description 55
- 238000006243 chemical reaction Methods 0.000 claims description 49
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 43
- -1 formyloxy group Chemical group 0.000 claims description 42
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 32
- 125000000538 pentafluorophenyl group Chemical group FC1=C(F)C(F)=C(*)C(F)=C1F 0.000 claims description 31
- 125000004217 4-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C([H])([H])* 0.000 claims description 29
- 239000000203 mixture Substances 0.000 claims description 22
- 150000003839 salts Chemical class 0.000 claims description 19
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 18
- 150000008052 alkyl sulfonates Chemical class 0.000 claims description 17
- 238000002360 preparation method Methods 0.000 claims description 17
- 150000001412 amines Chemical class 0.000 claims description 15
- 239000003054 catalyst Substances 0.000 claims description 14
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 14
- 150000004678 hydrides Chemical class 0.000 claims description 12
- 229910052727 yttrium Inorganic materials 0.000 claims description 12
- 125000003277 amino group Chemical group 0.000 claims description 11
- 150000003222 pyridines Chemical class 0.000 claims description 11
- 238000006254 arylation reaction Methods 0.000 claims description 10
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 10
- 238000005984 hydrogenation reaction Methods 0.000 claims description 9
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 9
- UKVQBONVSSLJBB-UHFFFAOYSA-N 2-pyridin-2-ylacetonitrile Chemical class N#CCC1=CC=CC=N1 UKVQBONVSSLJBB-UHFFFAOYSA-N 0.000 claims description 8
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 8
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 8
- 238000005859 coupling reaction Methods 0.000 claims description 8
- 125000006239 protecting group Chemical group 0.000 claims description 8
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 7
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 6
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 5
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- IVPBACHRSWYPTP-UHFFFAOYSA-N 2-cyano-2-pyridin-2-ylacetic acid Chemical class OC(=O)C(C#N)C1=CC=CC=N1 IVPBACHRSWYPTP-UHFFFAOYSA-N 0.000 claims description 4
- 125000004011 3 membered carbocyclic group Chemical group 0.000 claims description 4
- 125000001845 4 membered carbocyclic group Chemical group 0.000 claims description 4
- 125000001054 5 membered carbocyclic group Chemical group 0.000 claims description 4
- 125000004008 6 membered carbocyclic group Chemical group 0.000 claims description 4
- 238000005903 acid hydrolysis reaction Methods 0.000 claims description 4
- 230000002378 acidificating effect Effects 0.000 claims description 4
- 230000029936 alkylation Effects 0.000 claims description 4
- 238000005804 alkylation reaction Methods 0.000 claims description 4
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 4
- 125000000440 benzylamino group Chemical group [H]N(*)C([H])([H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 4
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 4
- 239000003153 chemical reaction reagent Substances 0.000 claims description 4
- MLIREBYILWEBDM-UHFFFAOYSA-N cyanoacetic acid Chemical class OC(=O)CC#N MLIREBYILWEBDM-UHFFFAOYSA-N 0.000 claims description 4
- 238000010511 deprotection reaction Methods 0.000 claims description 4
- 238000006073 displacement reaction Methods 0.000 claims description 4
- 150000004820 halides Chemical class 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- 238000010438 heat treatment Methods 0.000 claims description 4
- 230000007062 hydrolysis Effects 0.000 claims description 4
- 238000006460 hydrolysis reaction Methods 0.000 claims description 4
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 4
- 238000010992 reflux Methods 0.000 claims description 4
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical group NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 claims description 3
- 241000233866 Fungi Species 0.000 claims description 3
- 230000000855 fungicidal effect Effects 0.000 claims description 3
- 150000002500 ions Chemical class 0.000 claims description 3
- 229910052751 metal Inorganic materials 0.000 claims description 3
- 239000002184 metal Substances 0.000 claims description 3
- 230000003032 phytopathogenic effect Effects 0.000 claims description 3
- 241000196324 Embryophyta Species 0.000 claims 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims 3
- 241000894007 species Species 0.000 claims 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 claims 2
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 claims 2
- 150000002429 hydrazines Chemical class 0.000 claims 2
- 150000002466 imines Chemical class 0.000 claims 2
- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical class C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 claims 2
- 241000252073 Anguilliformes Species 0.000 claims 1
- 101000617818 Homo sapiens Solute carrier organic anion transporter family member 4A1 Proteins 0.000 claims 1
- 102100022004 Solute carrier organic anion transporter family member 4A1 Human genes 0.000 claims 1
- 230000004913 activation Effects 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 1
- 235000013399 edible fruits Nutrition 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 229910052752 metalloid Inorganic materials 0.000 claims 1
- 150000002738 metalloids Chemical class 0.000 claims 1
- 231100001184 nonphytotoxic Toxicity 0.000 claims 1
- 239000002689 soil Substances 0.000 claims 1
- 238000006467 substitution reaction Methods 0.000 claims 1
- 125000002348 vinylic group Chemical group 0.000 claims 1
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 9
- 239000002585 base Substances 0.000 description 9
- 239000003446 ligand Substances 0.000 description 6
- 239000003960 organic solvent Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 150000002940 palladium Chemical class 0.000 description 4
- 229910052763 palladium Inorganic materials 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- POIFKAIWAMHITC-UHFFFAOYSA-N n-(2-pyridin-2-ylethyl)benzamide Chemical class C=1C=CC=CC=1C(=O)NCCC1=CC=CC=N1 POIFKAIWAMHITC-UHFFFAOYSA-N 0.000 description 3
- 230000003287 optical effect Effects 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 150000001242 acetic acid derivatives Chemical class 0.000 description 2
- 125000002723 alicyclic group Chemical group 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 229910000102 alkali metal hydride Inorganic materials 0.000 description 2
- 150000008046 alkali metal hydrides Chemical class 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 150000001342 alkaline earth metals Chemical class 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 239000003849 aromatic solvent Substances 0.000 description 2
- RBFQJDQYXXHULB-UHFFFAOYSA-N arsane Chemical class [AsH3] RBFQJDQYXXHULB-UHFFFAOYSA-N 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 2
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 2
- 150000004679 hydroxides Chemical class 0.000 description 2
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 2
- 150000007530 organic bases Chemical class 0.000 description 2
- 150000003003 phosphines Chemical class 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 150000003512 tertiary amines Chemical class 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical group NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 229910010082 LiAlH Inorganic materials 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000011149 active material Substances 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 125000005194 alkoxycarbonyloxy group Chemical group 0.000 description 1
- 125000000304 alkynyl group Chemical group 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- HGTBZFMPHBAUCQ-KHZPMNTOSA-N cyclopentane;dicyclohexyl-[(1r)-1-(2-diphenylphosphanylcyclopentyl)ethyl]phosphane;iron Chemical compound [Fe].[CH]1[CH][CH][CH][CH]1.[C]1([C@@H](C)P(C2CCCCC2)C2CCCCC2)[CH][CH][CH][C]1P(C=1C=CC=CC=1)C1=CC=CC=C1 HGTBZFMPHBAUCQ-KHZPMNTOSA-N 0.000 description 1
- STAGMXYQPGLLTD-GHVWMZMZSA-N cyclopentane;ditert-butyl-[(1r)-1-(2-diphenylphosphanylcyclopentyl)ethyl]phosphane;iron Chemical compound [Fe].[CH]1[CH][CH][CH][CH]1.CC(C)(C)P(C(C)(C)C)[C@H](C)[C]1[CH][CH][CH][C]1P(C=1C=CC=CC=1)C1=CC=CC=C1 STAGMXYQPGLLTD-GHVWMZMZSA-N 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- DPOGTJDEMBEUSH-UHFFFAOYSA-N dicyclohexyl(ethyl)phosphane Chemical compound C1CCCCC1P(CC)C1CCCCC1 DPOGTJDEMBEUSH-UHFFFAOYSA-N 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 230000000361 pesticidal effect Effects 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 125000001424 substituent group Chemical group 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
- C07D213/62—Oxygen or sulfur atoms
- C07D213/70—Sulfur atoms
-
- 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
- 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
- C07D213/24—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 substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/36—Radicals substituted by singly-bound nitrogen atoms
- C07D213/40—Acylated substituent nitrogen atom
-
- 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
- C07D213/61—Halogen atoms or nitro radicals
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)
- Pyridine Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP03356116A EP1500651A1 (fr) | 2003-07-25 | 2003-07-25 | Composés de N-[2-(2-pyridinyl)éthyl]benzamide et leur utilisation comme fongicides |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200600691B true ZA200600691B (en) | 2008-05-28 |
Family
ID=33484064
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200600691A ZA200600691B (en) | 2003-07-25 | 2006-01-24 | N-'2-(2-pyridinyl) ethylbenzamide compounds and their use as fungicides |
Country Status (22)
| Country | Link |
|---|---|
| US (1) | US7723364B2 (fr) |
| EP (2) | EP1500651A1 (fr) |
| JP (1) | JP4857108B2 (fr) |
| KR (1) | KR101130600B1 (fr) |
| CN (1) | CN1826320B (fr) |
| AR (1) | AR045097A1 (fr) |
| AU (1) | AU2004262580B9 (fr) |
| BR (1) | BRPI0411501B1 (fr) |
| CA (1) | CA2532176C (fr) |
| CO (1) | CO5660288A2 (fr) |
| CR (1) | CR8197A (fr) |
| EC (1) | ECSP056220A (fr) |
| ES (1) | ES2529569T3 (fr) |
| IL (1) | IL172230A (fr) |
| MX (1) | MXPA06000889A (fr) |
| PL (3) | PL1651604T3 (fr) |
| PT (1) | PT1651604E (fr) |
| RU (1) | RU2352562C2 (fr) |
| TW (1) | TWI361185B (fr) |
| UA (1) | UA86594C2 (fr) |
| WO (1) | WO2005014545A2 (fr) |
| ZA (1) | ZA200600691B (fr) |
Families Citing this family (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TWI368482B (en) * | 2003-12-19 | 2012-07-21 | Bayer Sas | New 2-pyridinylethylbenzamide derivatives |
| EP1674455A1 (fr) * | 2004-12-21 | 2006-06-28 | Bayer CropScience S.A. | Procédé de préparation de dérivés de la 2-éthylaminopyridine |
| BRPI0516905B1 (pt) * | 2004-12-21 | 2016-09-20 | Bayer Cropscience Sa | processo para a preparação de um derivado n-[2-(2-piridinil)etil]carboxamida e compostos |
| WO2006117356A1 (fr) * | 2005-05-03 | 2006-11-09 | Bayer Cropscience Sa | Nouveaux derives d'heterocyclylethylbenzamide |
| WO2006122955A1 (fr) * | 2005-05-18 | 2006-11-23 | Bayer Cropscience Sa | Nouveaux derives 2-pyridinylcycloalkylcarboxamide utiles en tant que fongicides. |
| TWI435863B (zh) | 2006-03-20 | 2014-05-01 | Nihon Nohyaku Co Ltd | Ｎ-２-（雜）芳基乙基甲醯胺衍生物及含該衍生物之蟲害防治劑 |
| US20090318290A1 (en) * | 2006-07-06 | 2009-12-24 | Bayer Cropscience Sa | N-(4-pyridin-2-ylbutyl) benzamide derivatives and their use as fungicides |
| ATE489850T1 (de) | 2006-07-06 | 2010-12-15 | Bayer Cropscience Ag | Pestizidzusammensetzung mit einem pyridylethylbenzamidderivat und insektizidverbindung |
| WO2008046838A2 (fr) * | 2006-10-18 | 2008-04-24 | Bayer Cropscience Sa | Nouveaux dérivés de n-(3-pyridine-2-ylpropyl)benzamide |
| WO2008061866A1 (fr) * | 2006-11-20 | 2008-05-29 | Bayer Cropscience Sa | Nouveaux dérivés de benzamide |
| EP2589294A1 (fr) | 2011-11-02 | 2013-05-08 | Bayer CropScience AG | Composés dotés d'une activité nématicide |
| EP2589292A1 (fr) | 2011-11-02 | 2013-05-08 | Bayer CropScience AG | Composés dotés d'une activité nématicide |
| EP2606727A1 (fr) | 2011-12-21 | 2013-06-26 | Bayer CropScience AG | Composés dotés dýune activité nématicide |
| EP2606728A1 (fr) | 2011-12-21 | 2013-06-26 | Bayer CropScience AG | Composés dotés dýune activité nématicide |
| BR112014010714A2 (pt) | 2011-11-02 | 2017-05-02 | Bayer Ip Gmbh | compostos com atividade nematicida |
| US20140256728A1 (en) | 2011-11-02 | 2014-09-11 | Bayer Intellectual Property Gmbh | Compounds with nematicidal activity |
| US9422276B2 (en) | 2011-11-25 | 2016-08-23 | Bayer Intellectual Property Gmbh | Use of aryl and hetaryl carboxamides as endoparasiticides |
| TW201427947A (zh) | 2012-10-12 | 2014-07-16 | Lundbeck & Co As H | 環狀胺 |
| EP2730570A1 (fr) | 2012-11-13 | 2014-05-14 | Bayer CropScience AG | Pyridyloxyalkylcarboxamide et son utilisation comme endoparasiticide et nématicide |
| PL2986594T3 (pl) | 2013-04-15 | 2017-10-31 | Fmc Corp | Amidy grzybobójcze |
| UY35772A (es) | 2013-10-14 | 2015-05-29 | Bayer Cropscience Ag | Nuevos compuestos plaguicidas |
| WO2015125824A1 (fr) * | 2014-02-18 | 2015-08-27 | 日産化学工業株式会社 | Composé amide substitué par un groupe alkynylpyridine et agent de lutte contre des organismes nuisibles |
| BR112019012885B1 (pt) * | 2016-12-21 | 2022-12-27 | Bayer Cropscience Aktiengesellschaft | Processo para preparar derivados de 2-etilaminopiridina substituída |
| CN109293565B (zh) * | 2018-10-26 | 2021-08-06 | 江苏七洲绿色化工股份有限公司 | 一种氟吡菌酰胺的制备方法 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3900481A (en) * | 1974-04-01 | 1975-08-19 | Riker Laboratories Inc | Derivatives of pyrrolidine and piperidine |
| DE2417763A1 (de) * | 1974-04-11 | 1975-10-30 | Bayer Ag | Carbonsaeureamide, verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel |
| DE2428673A1 (de) * | 1974-06-14 | 1976-01-02 | Bayer Ag | Carbonsaeureamide, verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel |
| IL84944A (en) * | 1987-01-19 | 1992-02-16 | Ici Plc | Pharmaceutical compositions containing 1,2-dihydro-3h-indazolone derivatives,some new such compounds and their preparation |
| TW575562B (en) * | 1998-02-19 | 2004-02-11 | Agrevo Uk Ltd | Fungicides |
| EP1204323B1 (fr) * | 1999-08-18 | 2004-07-14 | Aventis CropScience GmbH | Fongicides |
| RU2003110962A (ru) * | 2000-09-18 | 2004-10-20 | Е.И.Дюпон де Немур энд Компани (US) | Пиридиниламиды и имиды для использования в качестве фунгицидов |
| EP1389614A1 (fr) * | 2002-08-12 | 2004-02-18 | Bayer CropScience S.A. | Nouveaux dérivés de N-[2-(2-pyridyl)éthyl]benzamide comme fongicides |
| EP1531673B1 (fr) * | 2002-08-12 | 2006-01-04 | Bayer CropScience S.A. | Nouveau derive de 2-pyridylethylbenzamide |
-
2003
- 2003-07-25 EP EP03356116A patent/EP1500651A1/fr not_active Withdrawn
-
2004
- 2004-06-24 TW TW093118326A patent/TWI361185B/zh not_active IP Right Cessation
- 2004-07-19 KR KR1020057023687A patent/KR101130600B1/ko active IP Right Grant
- 2004-07-19 PT PT47641378T patent/PT1651604E/pt unknown
- 2004-07-19 BR BRPI0411501-5A patent/BRPI0411501B1/pt not_active IP Right Cessation
- 2004-07-19 UA UAA200602052A patent/UA86594C2/uk unknown
- 2004-07-19 US US10/566,051 patent/US7723364B2/en not_active Expired - Fee Related
- 2004-07-19 CN CN2004800191713A patent/CN1826320B/zh not_active Expired - Fee Related
- 2004-07-19 RU RU2006105492/04A patent/RU2352562C2/ru not_active IP Right Cessation
- 2004-07-19 PL PL04764137T patent/PL1651604T3/pl unknown
- 2004-07-19 JP JP2006520820A patent/JP4857108B2/ja not_active Expired - Fee Related
- 2004-07-19 PL PL379385A patent/PL379385A1/pl unknown
- 2004-07-19 CA CA2532176A patent/CA2532176C/fr not_active Expired - Fee Related
- 2004-07-19 MX MXPA06000889A patent/MXPA06000889A/es active IP Right Grant
- 2004-07-19 ES ES04764137.8T patent/ES2529569T3/es not_active Expired - Lifetime
- 2004-07-19 AU AU2004262580A patent/AU2004262580B9/en not_active Ceased
- 2004-07-19 EP EP04764137.8A patent/EP1651604B1/fr not_active Expired - Lifetime
- 2004-07-19 WO PCT/EP2004/009145 patent/WO2005014545A2/fr active Application Filing
- 2004-07-19 PL PL407615A patent/PL407615A1/pl unknown
- 2004-07-23 AR ARP040102628A patent/AR045097A1/es not_active Application Discontinuation
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2005
- 2005-11-28 IL IL172230A patent/IL172230A/en active IP Right Grant
- 2005-12-13 EC EC2005006220A patent/ECSP056220A/es unknown
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2006
- 2006-01-17 CR CR8197A patent/CR8197A/es not_active Application Discontinuation
- 2006-01-24 ZA ZA200600691A patent/ZA200600691B/en unknown
- 2006-01-30 CO CO06008282A patent/CO5660288A2/es not_active Application Discontinuation
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