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1. (US20100144674) PYRIDAZINE DERIVATIVES
Note: Texte fondé sur des processus automatiques de reconnaissance optique de caractères. Seule la version PDF a une valeur juridique

Claims

1. A compound of formula I:

( MOL) ( CDX)
wherein
R 1 is hydrogen, C 1-C 6alkyl, C 1-C 6haloalkyl or C 3-C 6cycloalkyl;
R 2 is cycloalkyl, cycloalkylalkyl, halocycloalkyl, cycloalkoxy, halocycloalkoxy, cycloalkylalkoxy, halocycloalkylalkoxy, alkoxyalkyl, cycloalkoxyalkoxyalkyl, haloalkoxyalkyl, trialkylsilyl, alkylthioalkyl, haloalkylthioalkyl, cycloalkylthio, halocycloalkylthio, cycloalkylalkylthio, halocycloalkylalkylthio, alkylsulfinylalkyl, alkylsulfonylalkyl, alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, haloalkylsulfonyl, C 2-C 6alkenyl, C 2-C 6alkynyl, optionally substituted arylsulfonyl, optionally substituted aryloxy, optionally substituted heteroaryloxy, optionally substituted arylthio, optionally substituted heteroarylthio; or
R 2 together with an adjacent carbon atom forms an optionally substituted fused ring;
R 3 is an optionally substituted aryl;
R 4 is hydrogen, halogen, C 1-C 6alkyl, C 1-C 6haloalkyl, C 1-C 6alkoxy, C 1-C 6haloalkoxy, hydroxy or cyano; and
n is a whole number from 1 to 4;
or an agrochemically usable salt form thereof.
2. The compound according to claim 1 wherein R 1 is hydrogen, C 1-C 6alkyl or C 1-C 6haloalkyl.
3. The compound according to claim 1 wherein R 2 is cycloalkyl, cycloalkylalkyl, halocycloalkyl, cycloalkoxy, halocycloalkoxy, cycloalkylalkoxy, halocycloalkylalkoxy, alkoxyalkyl, cycloalkoxyalkoxyalkyl, haloalkoxyalkyl, trialkylsilyl, alkylthioalkyl, haloalkylthioalkyl, cycloalkylthio, halocycloalkylthio, cycloalkylalkylthio, halocycloalkylalkylthio, alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, haloalkylsulfonyl, C 2-C 6alkenyl, C 2-C 6alkynyl, optionally substituted arylsulfonyl, optionally substituted aryloxy, optionally substituted heteroaryloxy, optionally substituted arylthio, optionally substituted heteroarylthio; or
R 2 together with an adjacent carbon atom forms an optionally substituted 2- to 7-membered fused ring.
4. The compound according to claim 1 wherein R 3 is an optionally substituted phenyl.
5. The compound according to claim 1 wherein R 4 is halogen, C 1-C 6alkyl, C 1-C 6haloalkyl, C 1-C 6alkoxy, C 1-C 6haloalkoxy, hydroxy or cyano.
6. The compound according to claim 1 wherein n is whole number from 1 to 3.
7. The compound according to claim 1 wherein
R 1 is C 1-C 6alkyl or C 1-C 6haloalkyl;
R 2 is cycloalkyl, cycloalkylalkyl, halocycloalkyl, cycloalkoxy, cycloalkylalkoxy, alkoxyalkyl, cycloalkoxyalkoxyalkyl, haloalkoxyalkyl, trialkylsilyl, alkylthioalkyl, haloalkylthioalkyl, cycloalkylthio, halocycloalkylthio, cycloalkylalkylthio, halocycloalkylalkylthio, alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, haloalkylsulfonyl, C 2-C 6alkenyl, C 2-C 6alkynyl, optionally substituted arylsulfonyl, optionally substituted aryloxy, optionally substituted heteroaryloxy, optionally substituted arylthio, optionally substituted heteroarylthio; or
R 2 together with an adjacent carbon atom forms an optionally substituted 2- to 7-membered aromatic carbocyclic fused ring, an optionally substituted 2- to 7-membered non aromatic carbocyclic fused ring, an optionally substituted 2- to 7-membered aromatic heterocyclic fused ring or an optionally substituted 2- to 7-membered non aromatic heterocyclic fused ring;
R 3 is 2-fluorophenyl, 2-chlorophenyl, 2-trifluoromethylphenyl, 2-methylphenyl, 2,3-difluorophenyl, 2,4-difluorophenyl, 2,5-difluorophenyl, 2,6-difluorophenyl, 2,3-dichlorophenyl, 2,4-dichlorophenyl, 2,5-dichlorophenyl, 2,6-dichlorophenyl, 2-chloro-3-fluorophenyl, 2-chloro-4-fluorophenyl, 2-chloro-5-fluorophenyl, 2-chloro-6-fluorophenyl, 3-chloro-2-fluorophenyl, 4-chloro-2-fluorophenyl, 5-chloro-2-fluorophenyl, 2-fluoro-3-trifluoromethylphenyl, 2-fluoro-4-trifluoromethylphenyl, 2-fluoro-5-trifluoromethylphenyl, 2-fluoro-6-trifluoromethylphenyl, 2-chloro-3-trifluoromethylphenyl, 2-chloro-4-trifluoromethylphenyl, 2-chloro-5-trifluoromethylphenyl, 2-chloro-6-trifluoromethylphenyl, 4-fluoro-2-trifluoromethylphenyl, 4-chloro-2-trifluoromethylphenyl, 2-fluoro-3-methylphenyl, 2-fluoro-3-methylphenyl, 2-fluoro-4-methylphenyl, 2-fluoro-5-methylphenyl, 2-fluoro-6-methylphenyl, 2-chloro-3-methylphenyl, 2-chloro-4-methylphenyl, 2-chloro-5-methylphenyl, 2-chloro-6-methylphenyl, 4-fluoro-2-methylphenyl, 4-chloro-2-methylphenyl, 2,4,6-trifluorophenyl, 2,3,6-trifluorophenyl, 2,3,4-trifluorophenyl, 2,4,6-trichlorophenyl, 2,3,6-trichlorophenyl, 2,3,4-trichlorophenyl, 2,6-difluoro-4-methoxyphenyl, 2,6-difluoro-4-trifluoromethoxyphenyl, 2,6-difluoro-4-trifluoromethylphenyl, 2,6-difluoro-4-cyanoyphenyl, 2,6-difluoro-4-cyanoyphenyl, 2,6-difluoro-4-cyanoyphenyl, 2,6-difluoro-4-methylphenyl, 2,6-dichloro-4-methoxyphenyl, 2,6-dichloro-4-methoxyphenyl, 2,6-dichloro-4-methoxyphenyl, 2,6-dichloro-4-trifluoromethoxyphenyl, 2,6-dichloro-4-trifluoromethylphenyl, 2,6-dichloro-4-cyanophenyl, 2,6-dichloro-4-cyanophenyl, 2,6-dichloro-4-cyanophenyl, 2,6-dichloro-4-methylphenyl or pentafluorophenyl;
R 4 is halogen, C 1-C 6alkyl, C 1-C 6haloalkyl, C 1-C 6alkoxy, C 1-C 6haloalkoxy or hydroxy; and
n is a whole number from 1 to 3.
8. The compound according to claim 1 wherein
R 1 is C 1-C 6alkyl;
R 2 is cycloalkyl, cycloalkylalkyl, halocycloalkyl, cycloalkoxy, cycloalkylalkoxy, alkoxyalkyl, haloalkoxyalkyl, trialkylsilyl, alkylthioalkyl, haloalkylthioalkyl, cycloalkylthio, cycloalkylalkylthio, halocycloalkylalkylthio, alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, haloalkylsulfonyl, C 2-C 6alkenyl, C 2-C 6alkynyl, optionally substituted arylsulfonyl, optionally substituted aryloxy, optionally substituted heteroaryloxy, optionally substituted arylthio, optionally substituted heteroarylthio; or
R 2 together with an adjacent carbon atom forms an optionally substituted 3- to 7-membered aromatic carbocyclic fused ring, an optionally substituted 3- to 7-membered non aromatic carbocyclic fused ring, an optionally substituted 3- to 7-membered aromatic heterocyclic fused ring or an optionally substituted 3- to 7-membered non aromatic heterocyclic fused ring;
R 3 is 2-fluorophenyl, 2-chlorophenyl, 2-trifluoromethylphenyl, 2-methylphenyl, 2,3-difluorophenyl, 2,4-difluorophenyl, 2,5-difluorophenyl, 2,6-difluorophenyl, 2,3-dichlorophenyl, 2,4-dichlorophenyl, 2,5-dichlorophenyl, 2,6-dichlorophenyl, 2-chloro-3-fluorophenyl, 2-chloro-4-fluorophenyl, 2-chloro-5-fluorophenyl, 2-chloro-6-fluorophenyl, 3-chloro-2-fluorophenyl; 4-chloro-2-fluorophenyl, 2,4,6-trifluorophenyl, 2,3,6-trifluorophenyl, 2,3,4-trifluorophenyl, 2,4,6-trichlorophenyl, 2,3,6-trichlorophenyl, 2,3,4-trichlorophenyl, 2,6-difluoro-4-methoxyphenyl, 2,6-difluoro-4-trifluoromethoxyphenyl, 2,6-difluoro-4-trifluoromethylphenyl, 2,6-difluoro-4-cyanoyphenyl, 2,6-difluoro-4-cyanoyphenyl, 2,6-difluoro-4-cyanoyphenyl, 2,6-difluoro-4-methylphenyl, 2,6-dichloro-4-methoxyphenyl, 2,6-dichloro-4-methoxyphenyl, 2,6-dichloro-4-methoxyphenyl, 2,6-dichloro-4-trifluoromethoxyphenyl, 2,6-dichloro-4-trifluoromethylphenyl, 2,6-dichloro-4-cyanophenyl, 2,6-dichloro-4-cyanophenyl, 2,6-dichloro-4-cyanophenyl, 2,6-dichloro-4-methylphenyl or pentafluorophenyl;
R 4 is halogen, C 1-C 6alkyl, C 1-C 6haloalkyl, C 1-C 6alkoxy or hydroxy;
n is a whole number from 1 to 3.
9. The compound according to claim 1 wherein
R 1 is C 1-C 3alkyl;
R 2 is cycloalkyl, cycloalkylalkyl, halocycloalkyl, cycloalkoxy, cycloalkylalkoxy, alkoxyalkyl, haloalkoxyalkyl, trialkylsilyl, alkylthioalkyl, haloalkylthioalkyl, cycloalkylthio, cycloalkylalkylthio, alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, haloalkylsulfonyl, optionally substituted arylsulfonyl, optionally substituted aryloxy, optionally substituted heteroaryloxy, optionally substituted arylthio, optionally substituted heteroarylthio; or
R 2 together with an adjacent carbon atom forms an optionally substituted 3- to 6-membered aromatic carbocyclic fused ring, an optionally substituted 3- to 6-membered non aromatic carbocyclic fused ring or an optionally substituted 3- to 6-membered aromatic heterocyclic fused ring;
R 3 is 2-fluorophenyl, 2-chlorophenyl, 2-trifluoromethylphenyl, 2-methylphenyl, 2,3-difluorophenyl, 2,4-difluorophenyl, 2,5-difluorophenyl, 2,6-difluorophenyl, 2-chloro-3-fluorophenyl, 2-chloro-4-fluorophenyl, 2-chloro-5-fluorophenyl, 2-chloro-6-fluorophenyl, 2,4,6-trifluorophenyl, 2,3,6-trifluorophenyl, 2,3,4-trifluorophenyl;
R 4 is halogen, C 1-C 6alkyl, C 1-C 6alkoxy or hydroxy; and
n is a whole number from 1 to 2.
10. The compound according to claim 1 wherein
R 1 is methyl;
R 2 is cycloalkoxy, cycloalkylalkoxy, alkylsulfonyl, optionally substituted aryloxy; or
R 2 together with an adjacent carbon atom forms an optionally substituted 6-membered aromatic carbocyclic fused ring;
R 3 is 2-methylphenyl, 2,6-difluorophenyl, 2-chloro-6-fluorophenyl or 2,4,6-trifluorophenyl;
R 4 is fluoro, chloro, methyl, methoxy or hydroxy; and
n is a whole number from 1 to 2.
11. A compound selected from
3-chloro-5-(4-cyclopropylphenyl)-6-methyl-4-(2,4,6-trifluorophenyl)-pyridazine,
3-chloro-5-(4-methanesulfonylphenyl)-6-methyl-4-(2,4,6-trifluorophenyl)-pyridazine,
3-chloro-6-methyl-5-naphthalen-2-yl-4-(2,4,6-trifluorophenyl)-pyridazine,
3,6-dimethyl-4-naphthalen-2-yl-5-(2,4,6-trifluorophenyl)-pyridazine,
4-(2-chloro-6-fluorophenyl)-3-methoxy-6-methyl-5-naphthalen-2-yl-pyridazine,
4-(2-chloro-6-fluorophenyl)-3,6-dimethyl-5-naphthalen-2-yl-pyridazine,
3-fluoro-6-methyl-5-naphthalen-2-yl-4-(2,4,6-trifluoro-phenyl)-pyridazine,
3-methoxy-6-methyl-5-naphthalen-2-yl-4-(2,4,6-trifluoro-phenyl)-pyridazine,
3-chloro-5-[4-(4-chlorophenoxy)-phenyl]-6-methyl-4-(2,4,6-trifluorophenyl)-pyridazine,
3-chloro-6-methyl-5-(4-phenoxyphenyl)-4-(2,4,6-trifluorophenyl)-pyridazine,
3-chloro-6-methyl-5-(4-phenylsulfanylphenyl)-4-(2,4,6-trifluorophenyl)-pyridazine,
3-chloro-5-[4-(4-chlorophenylsulfanyl)-phenyl]-6-methyl-4-(2,4,6-trifluorophenyl)-pyridazine,
3-chloro-6-methyl-5-(4-trifluoromethanesulfonylphenyl)-4-(2,4,6-trifluorophenyl)-pyridazine,
3-chloro-5-(4-cyclopentyloxyphenyl)-6-methyl-4-(2,4,6-trifluorophenyl)-pyridazine,
3-chloro-5-(4-methoxymethylphenyl)-6-methyl-4-(2,4,6-trifluorophenyl)-pyridazine,
3-chloro-6-methyl-5-(4-methylsulfanylmethylphenyl)-4-(2,4,6-trifluorophenyl)-pyridazine, and
3-chloro-5-(4-cyclopropylmethylphenyl)-6-methyl-4-(2,4,6-trifluorophenyl)-pyridazine.
12. A process for the preparation of a compound of formula I.1,

( MOL) ( CDX)
wherein R 1, R 2, R 3 and n are as defined for compound of formula I and Hal is halogen, which comprises reacting a compound of formula I.5,

( MOL) ( CDX)
wherein R 1, R 2, R 3 and n are as defined for compound of formula I, with a phosphorus oxyhalide or a thionyl halide.
13. A process for the preparation of a compound of formula I.5,

( MOL) ( CDX)
wherein R 1, R 2, R 3 and n are as defined for compound of formula I, which comprises reacting a compound of formula II,

( MOL) ( CDX)
wherein R 1, R 2, R 3 and n are as defined for compound of formula I, with a hydrazine derivative.
14. A process for the preparation of a compound of formula II,

( MOL) ( CDX)
wherein R 1, R 2, R 3 and n are as defined for compound of formula I, which comprises an oxidation of a compound of formula III,

( MOL) ( CDX)
wherein R 1, R 2, R 3 and n are as defined for compound of formula I, with oxygen, air or 3-chloroperbenzoic acid.
15. A process for the preparation of a compound of formula III,

( MOL) ( CDX)
wherein R 1, R 2, R 3 and n are as defined for compound of formula I, which comprises reacting a compound of formula IV,

( MOL) ( CDX)
wherein R 1, R 2, R 3 and n are as defined for compound of formula I, with a base.
16. A fungicidal composition for controlling or protecting against phytopathogenic microorganisms, comprising as active ingredient at least one compound as defined in claim 1, in free form or in agrochemically usable salt form, and at least one adjuvant.
17. The composition according to claim 16, which comprises at least one additional fungicidally active compound, preferably selected from the group consisting of azoles, pyrimidinyl carbinoles, 2-amino-pyrimidines, morpholines, anilinopyrimidines, pyrroles, phenylamides, benzimidazoles, dicarboximides, carboxamides, strobilurines, dithiocarbamates, N-halomethylthiotetrahydrophthalimides, copper-compounds, nitrophenols, organo-phosphorus-derivatives, pyridazines, triazolopyrimidines, carboxamides or benzamides.
18. (canceled)
19. A method of controlling or preventing an infestation of crop plants, harvested food crops or non-living materials by phytopathogenic or spoilage microorganisms or organisms potentially harmful to man, which comprises the application of a compound as defined in claim 1, as active ingredient to the plant, to parts of the plants or to the locus thereof, to seeds or to any part of the non-living materials.
20. The method according to claim 19, wherein the phytopathogenic microorganisms are fungal organisms.