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US 2001/0011064 A1Published application
Herbicidal 3,5-difluoropyridines
AssigneeAmerican Cyanamid Company
InventorsThomas Maier, Stefan Scheiblich, Helmut S. Baltruschat
Life of this patent
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Abstract
The invention relates to novel compounds of formula I: 1 wherein R, A, B and X have the meaning given in claim 1; and the agronomically acceptable salts or N-oxides thereof, and to herbicidal compositions containing such compounds as active ingredients.
Claims15
A compound of the general formula (I) 16
- wherein
- A represents an optionally substituted aryl group or an optionally substituted 5- or 6-membered nitrogen-containing heteroaromatic group or a difluorobenzodioxolyl group;
- B represents an optionally substituted phenyl or thienyl group;
- R represents a halogen atom or an optionally substituted alkyl, alkenyl, alkinyl, alkoxy, alkoxyalkyl, alkylthio, alkylamino, dialkylamino, alkylsulphinyl, alkylsulphonyl group or a nitro, cyano, hydroxy, amino, haloalkyl, haloalkoxy, haloalkylthio or SF5 group, and
- X represents an oxygen or a sulfur atom;
- and the agronomically acceptable salts or N-oxides thereof.
3 more elements
A compound as claimed in any of the preceding claims, wherein B represents a phenyl or thienyl group being substituted by one or more of the same or different substituents selected from halogen atoms, alkyl groups, alkoxy groups, cyano groups, haloalkyl groups, haloalkoxy groups alkylthio groups, haloalkylthio groups and SF5 groups.
A compound as claimed in any of the preceding claims, wherein X is oxygen.
A compound of formula IA 17
- wherein A represents 3-trifluoromethylphenyl, 2-chloropyrid-4-yl, 2-trifluoromethylpyrid-4-yl, 2-difluoromethoxypyrid-4-yl or 1-methyl-3-trifluoromethylpyrazol-5-yl, R has the meaning given above;
- R2 each independently represent a hydrogen atom or a fluorine atom, one or two of them also a chlorine or bromine or a trifluoromethyl, trifluormethoxy or a cyano group, one of them can further be a C1-C4-alkyl group, particularly tert-butyl, and m is 0 or an integer selected from 1 to 5, in particular 1 to 2.
A compound selected from the group consisting
- 3,5-difluoro-4-methyl-2-(1′-methyl-3′-trifluoromethylpyrazol-5′-yloxy)-6-(4″-trifluoromethylphenyl)pyridine
- 3,5-difluoro-4-methyl-2-(3′-trifluoromethylphenoxy)-6-(4″-trifluoromethylphenyl)pyridine
- 3,5-difluoro-4-ethyl-2-(3′-trifluoromethylphenoxy)-6-(4″-trifluoromethylphenyl)pyridine
- 3,5-difluoro-4-ethyl-2-(1′-methyl-3′-trifluoromethylpyrazol-5′-yloxy)-6-(4″-trifluoromethylphenyl)pyridine
- 6-(4′-chlorophenyl)-3,5-difluoro-4-methyl-2-(1″-methyl-3″-trifluoromethylpyrazol-5″-yloxy)pyridine
- 6-(4′-chlorophenyl)-3,5-difluoro-4-methyl-2-(3″-trifluoromethylphenoxy)pyridine
- 2-(2′-chloropyrid-4′-yloxy)-3,5-difluoro-4-methyl-6-(4″-trifluoromethylphenyl)pyridine
- 3,5-difluoro-4-methyl-2-(2′-trifluoromethylpyrid-4′-yloxy)-6-(4″-trifluoromethylphenyl)pyridine
- 3,5-difluoro-2-(2′-difluoromethoxypyrid-4′-yloxy)-4-methyl-6-(4″-trifluoromethylphenyl)pyridine
- 6-(5″-chlorothien-2″-yl)-3,5-difluoro-4-methyl-2-(1′-methyl-3′-trifluoromethylpyrazol-5′-yloxy)-pyridine
- 2-(2′-chloropyrid-4′-yloxy)-3,5-difluoro-4-methyl-6-(3″-trifluoromethylphenyl)pyridine
- 3,5-difluoro-4-methyl-2-(1′-methyl-3′-trifluoromethylpyrazol-5′-yloxy)-6-(5″-trifluoromethylthien-2″-yl)pyridine
- 3,5-difluoro-4-methyl-2-(1′-methyl-3′-trifluoromethylpyrazol-5′-yloxy)-6-(4″-fluorophenyl)pyridine
- 3,5-difluoro-4-methoxy-2-(1′-methyl-3′-trifluoromethylpyrazol-5′-yloxy)-6-(4″-trifluoromethylphenyl)pyridine
- 3,5-difluoro-4-ethoxy-2-(1′-methyl-3′-trifluoromethylpyrazol-5′-yloxy)-6-(4″-trifluoromethylphenyl)pyridine
- 3,5-difluoro-4-methoxy-2-(3′-trifluoromethylphenoxy)-6-(4″-trifluoromethylphenyl)pyridine
- 3,5-difluoro-4-methyl-2-(2′-cyanopyrid-4′-yloxy)-6-(4″-trifluoromethylphenyl)pyridine
- 3,5-difluoro-4-methyl-2-(1′-methyl-3′-cyanopyrazol-5′-yloxy)-6-(4″-trifluoromethylphenyl)pyridine
- 3,5-difluoro-2-(3′-difluoromethoxyphenoxy)-4-methyl-6-(4″-trifluoromethylphenyl)pyridine
- 3,5-difluoro-4-methyl-2-(3′-trifluoromethoxyphenoxy)-6-(4″-trifluoromethylphenyl)pyridine
- 2-(3′-cyanophenoxy)-3,5-difluoro-4-methyl-6-(4″-trifluoromethylphenyl)pyridine
- 3,5-difluoro-4-methyl-2-(1′-methyl-3′-isopropylpyrazol-5′-yloxy)-6-(4″-trifluoromethylphenyl)pyridine
- 3,5-difluoro-4-methyl-2-(1′-methyl-3′-difluoromethoxypyrazol-5′-yloxy)-6-(4″-trifluoromethylphenyl)pyridine
- 3,5-difluoro-4-methyl-2-(2′-(2″,2″,2″-trifluoroethoxy)pyrid-4′-yloxy)-6-(4′″-trifluoro-methylphenyl)pyridine
- 3,5-difluoro-4-methyl-6-(4′-trifluoromethylphenyl)-2-(3″-trifluoromethylthiophenoxy)pyridine
- 3,5-difluoro-4-methyl-6-(4′-tert-butyl-phenyl)-2-(3″-trifluoromethylphenoxy)pyridine
- 3,5-difluoro-4-methyl-2-(1′-ethyl-3′-trifluoromethylpyrazol-5′-yloxy)-6-(4″-trifluoromethylphenyl)pyridine
- 3,5-difluoro-4-methyl-6-(4′-isopropylphenyl)-2-(3″-trifluoromethylphenoxy)pyridine
- 6-(4′-bromophenyl)-3,5-difluoro-4-methyl-2-(3″-trifluoromethylphenoxy)pyridine
- 3,5-difluoro-4-methyl-2-(1′-methyl-3′-trifluoromethyl-4′-fluoropyrazol-5′-yloxy)-6-(4″-trifluoromethylphenyl)pyridine
- 3,5-difluoro-4-methyl-2-(1′-methyl-3′-trifluoromethyl-4′-chloropyrazol-5′-yloxy)-6-(4″-trifluoromethylphenyl)pyridine
- 3,5-difluoro-4-methyl-2-(1′-methyl-3′-trifluoromethylpyrazol-5′-yloxy)-6-(4″-trifluoromethoxyphenyl)pyridine
- 3,5-difluoro-4-methyl-2-(1′-methyl-3′-trifluoromethylpyrazol-5′-yloxy)-6-(4″-trifluoromethylthiophenyl)pyridine
- 3,5-difluoro-6-(4′-difluoromethylthiophenyl)-4-methyl-2-(1″-methyl-3″-trifluoromethylpyrazol-5″-yloxy)pyridine
- 3,5-difluoro-4-methyl-6-(4′-ethylphenyl)-2-(1″-methyl-3″-trifluoromethylpyrazol-5″-yloxy)pyridine
- 3,5-difluoro-6-(3′,4′-difluorophenyl)-4-methyl-2-(1″-methyl-3″-trifluoromethylpyrazol-5″-yloxy)pyridine
- 3,5-difluoro-6-(2′,4′-difluorophenyl)-4-methyl-2-(1″-methyl-3″-trifluoromethylpyrazol-5″-yloxy)pyridine
- 3,5-difluoro-4-chloro-2-(1′-methyl-3′-trifluoromethylpyrazol-5′-yloxy)-6-(4″-trifluoromethylphenyl)pyridine
- 3,5-difluoro-4-chloro-2-(3′-trifluoromethylphenoxy)-6-(4″-trifluoromethylphenyl)pyridine
- 3,5-difluoro-4-methylthio-2-(1′-methyl-3′-trifluoromethylpyrazol-5′-yloxy)-6-(4″-trifluoromethylphenyl)pyridine
- 3,5-difluoro-4-methylthio-2-(3′-trifluoromethylphenoxy)-6-(4″-trifluoromethyl-phenyl)pyridine
- 4-cyano-3,5-difluoro-2-(1′-methyl-3′-trifluoromethylpyrazol-5′-yloxy)-6-(4″-trifluoromethylphenyl)pyridine
- 4-cyano-3,5-difluoro-2-(3′-trifluoromethylphenoxy)-6-(4″-trifluoromethylphenyl)pyridine
- 6-(4′-chlorophenyl)-4-cyano-3,5-difluoro-2-(1″-methyl-3″-trifluoromethylpyrazol-5″-yloxy)pyridine
- 6-(4′-chlorophenyl)-4-cyano-3,5-difluoro-2-(3″-trifluoromethylphenoxy)pyridine
- 2-(2′-chloropyrid-4′-yloxy)-4-cyano-3,5-difluoro-6-(4″-trifluoromethylphenyl)pyridine
- 4-cyano-3,5-difluoro-2-(2′-trifluoromethylpyrid-4′-yloxy)-6-(4″-trifluoromethylphenyl)pyridine
- 6-(5″-chlorothien-2″-yl)-4-cyano-3,5-difuoro-2-(1′-methyl-3′-trifluoromethylpyrazol-5′-yloxy)-pyridine.
45 more elements
A process for the preparation of a compound of general formula I, which comprises reacting a respective compound of the general formula II, 18
- in which A, R and n have the meaning given and L is a leaving group, with a compound of general formula III, 19
- in which B, and m have the meaning given, and
- M represents a free or complexed metal selected from the group consisting of Li, Mg, Zn, B, Sn,
- preferably under the conditions of a cross coupling reaction.
1 more element
Dependencies are inferred from the claim text.