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filingDate 2008-12-04-04:00^^<http://www.w3.org/2001/XMLSchema#date>
publicationDate 2010-02-03-04:00^^<http://www.w3.org/2001/XMLSchema#date>
publicationNumber AR-069580-A1
titleOfInvention PIRIDILMETIL-SULFONAMIDE COMPOUNDS, METHODS AND INTERMEDIARIES FOR THEIR PREPARATION, AN AGRICULTURAL COMPOSITION THAT UNDERSTANDS THEM, A METHOD TO COMBAT PHYTO-PATHOGENIC FUNGI THAT USES THEM, USE OF THESE COMPOUNDS FOR SUCH PURPOSE AND SEEDS.
abstract Its use, to combat harmful phytopathogenic fungi and also with compositions and seeds comprising at least said compound. Methods for their preparation and synthesis intermediaries are also provided. Claim 1: Pyridylmethyl sulfonamide compounds characterized in that they have the formula (1) wherein: n indicates the amount of substituents R1 in the pyridine ring and n is 0, 1, 2, 3 or 4; m indicates the amount of substituents R3 in the phenyl ring and m is 0, 1, 2, 3 or 4; R1 is halogen, CN, NO2, OH, SH, C1-4 alkyl, C1-4 haloalkyl, C1-4 alkoxy, C1-4 haloalkoxy, C1-4 alkylthio, C1-4 haloalkylthio, C1-4 alkylsulfinyl, C1- haloalkylsulfinyl 4, C1-4 alkylsulfonyl, C1-4 haloalkylsulfonyl, amino, C1-4 alkylamino, di (C1-4 alkyl) amino, C1-4 alkoxy-C1-4 alkyl, C2-4 alkenyl, C2-4 alkynyl, C3 cycloalkyl -8 or C1-4 alkyl-C3-8 cycloalkyl; and / or two R1 radicals that bind adjacent carbon atoms of the pyridine ring can form, together with said carbon atoms, a fused benzene ring, a fused 5, 6 or 7 membered carbocycle fused saturated or partially unsaturated or a fused 5, 6 or 7-membered heterocycle containing 1, 2 or 3 heteroatoms selected from the group consisting of 2 nitrogen atoms, 1 oxygen atom and 1 sulfur atom as ring members, where it is possible for the fused ring bearing 1 or 2 radicals selected from the group consisting of halogen, C1-4 alkyl, halomethyl, C1-4 alkoxy or halomethoxy, where it is possible for n = 2, 3 or 4 that R1 is identical or different; R 2 is hydrogen, C 1-4 alkyl, C 1-4 haloalkyl, C 2-4 alkenyl, C 2-4 alkynyl, C 3-8 cycloalkyl, C 1-4 alkyl C 3-8 cycloalkyl or benzyl wherein the benzyl phenyl portion is unsubstituted or carries 1, 2, 3, 4 or 5 substituents selected from the group consisting of cyano, halogen, C1-4 alkyl, C1-4 haloalkyl, C1-4 alkoxy, C1-4 haloalkoxy, C1-4 alkoxycarbonyl and di- ( C1-4 alkyl) aminocarbonyl; R3 is halogen, CN, NO2, C1-4 alkyl, C1-4 haloalkyl, C1-4 alkoxy, or C1-4 haloalkoxy, where it is possible for m = 2, 3 or 4 that R3 is identical or different; Y is a divalent group selected from -O-, C1-4 alkanediyl, -O-CH2-, -CH2-O-, -C (NORn) -, -S-, S (= O) -, S (= O ) 2 and -N (Rn) -, wherein Rn is hydrogen or C1-4 alkyl and wherein the C1-4 alkanediyl moiety is unsubstituted or carries 1 or 2 substituents selected from the group consisting of oxo, cyano, halogen, C1-4 alkyl, C1-4 alkoxy, C1-4 haloalkyl and C1-4 haloalkoxy; Het is a 5- or 6-membered heteroaromatic radical, in which the atoms of the heteroaromatic radical ring member include, in addition to carbon atoms, 1, 2, 3 or 4 nitrogen atoms or 1 oxygen atom and 0, 1 or 2 nitrogen atoms or 1 sulfur atom and 0, 1 or 2 nitrogen atoms and wherein the heteroaromatic radical is unsubstituted or carries 1, 2, 3 or 4 identical or different Ra substituents, where two Ra radicals that are attached At atoms of adjacent ring members they can form a fused 5 or 6 membered carbocycle or heterocycle, wherein the fused carbocycle or heterocycle is unsubstituted or carries 1, 2, 3 or 4 identical or different Rb substituents; Ra is halogen, CN, NO2, C1-4 alkyl, C1-4 haloalkyl, C2-4 alkenyl, C2-4 alkynyl, C1-4 alkoxy, C1-4 haloalkoxy, C1-4 alkylthio, C1-4 haloalkyl, C1 alkylsulfinyl -4, C1-4 haloalkylsulfinyl, C1-4 alkylsulfonyl, C1-4 haloalkylsulfonyl, amino, C1-4 alkylamino, di (C1-4 alkyl) amino, C1-4 alkoxy-C1-4 alkyl, a C radical (= O ) R, wherein R is H, C 1-4 alkyl, C 1-4 haloalkyl, C 2-4 alkenyl, C 2-4 alkynyl, C 1-4 alkoxy, C 1-4 alkoxy-C 1-4 alkoxy, C 1-4 haloalkoxy, amino , C1-4 alkylamino or di (C1-4 alkyl) amino; a radical CR '(= NOR' '), wherein R' is H or C1-4 alkyl and R '' is C1-4 alkyl, C1-4 haloalkyl, C2-4 alkenyl, C2-4 alkynyl or C1- alkoxy 4-C 1-4 alkyl, phenyl, pyridinyl, pyrimidinyl, phenoxy or phenoxyalkyl, wherein the last five radicals mentioned are unsubstituted or carry 1, 2, 3 or 4 identical or different Rc substituents; Rb and Rc are independently selected from halogen, CN, NO2, OH, SH, C1-4 alkyl, C1-4 haloalkyl, C1-4 alkoxy and C1-4 haloalkoxy; and the N-oxides and salts acceptable in agriculture of the compounds of the formula (1). Claim 7: A process for preparing pyridylmethyl sulfonamide compounds of the formula (1) as defined in any one of claims 1 to 6, characterized in that it comprises reacting an aminomethylpyridine compound of the formula (2) wherein n, R1 and R2 are as defined in claim 1, under basic conditions with a sulfonic acid derivative of the formula (3) wherein Y, Het, m and R3 are as defined in claim 1 and L is a leaving group as halogen, hydroxy, azido, optionally substituted heteroaryl, optionally substituted heteroaryloxy or optionally substituted phenoxy, preferably chloro, fluoro, optionally substituted heteroaryl such as pyrazol-1-yl, imidazol-1-yl, 1,2,3-triazol-1 -yl and optionally substituted 1,2,4-triazol-1-yl, pentafluorophenoxy or hydroxybenzotriazoloxy. Claim 8: A process for preparing pyridylmethyl sulfonamide compounds of the formula (1) as defined in any of claims 1 to 6, characterized in that it comprises reacting a compound of the formula (4) wherein n and R 1 are as is defined in claim 1 and L 'is a leaving group such as methylsulfonyl, toluenesulfonyl or as defined for L in the formula (3) in claim 7, under basic conditions with the compound of formula (5) wherein Y, Het , m, R2 and R3 are as defined in claim 1. Claim 9: Compounds characterized in that they have the formula (2), wherein R2 is defined according to claim 1, n is 2 and R1 is in position 2 and 3 of the pyridine ring and where R1 in position 2 is different from R1 in position 3 and if one of the two R1 is CH3, the other R1 is not OCH3. Claim 10: Compounds characterized in that they have the formula (3), wherein R3, Y and Het are defined according to claim 1, L is halogen and m is 1, 2, 3 or 4.
priorityDate 2007-12-05-04:00^^<http://www.w3.org/2001/XMLSchema#date>
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