PYRIDAZINE DERIVATIVES

Information

  • Patent Application
  • 20100144674
  • Publication Number
    20100144674
  • Date Filed
    October 23, 2007
    17 years ago
  • Date Published
    June 10, 2010
    14 years ago
Abstract
The present invention relates to novel pyridazine derivatives of formula (I) as active ingredients which have microbiocidal activity, in particular fungicidal activity: wherein R1 is hydrogen, C1-C6alkyl, C1-C8haloalkyl or C3-C6cycloalkyl; R2 is cycloalkyl, cycloalkylalkyl, halocycloalkyl, cycloalkoxy, halocycloalkoxy, cycloalkylalkoxy, halocycloalkylalkoxy, alkoxyalkyl, cycloalkoxyalkoxyalkyl, haloalkoxyalkyl, trialkylsilyl, alkylthioalkyl, haloalkylthioalkyl, cycloalkylthio, halocycloalkylthio, cycloalkylalkylthio, halocycloalkylalkylthio, alkylsulfinylalkyl, alkylsulfonylalkyl, alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, haloalkylsulfonyl, C2-C6alkenyl, C2-C6alkynyl, optionally substituted arylsulfonyl, optionally substituted aryloxy, optionally optionally substituted heteroaryloxy, optionally substituted arylthio, optionally substituted heteroarylthio; or R2 together with an adjacent carbon atom forms an optionally substituted fused ring; R3 is an optionally substituted aryl; R4 is hydrogen, halogen, C1-C6alkyl, C1-C6haloalkyl, C1-C8alkoxy, C1-C6haloalkoxy, hydroxy or cyano; and n is a whole number from 1 to 4; or an agrochemically usable salt form thereof.
Description

The present invention relates to novel pyridazine derivatives as active ingredients which have microbiocidal activity, in particular fungicidal activity. The invention also relates to preparation of these active ingredients, to novel heterocyclic derivatives used as intermediates in the preparation of these active ingredients, to preparation of these novel intermediates, to agrochemical compositions which comprise at least one of the novel active ingredients, to preparation of these compositions and to use of the active ingredients or compositions in agriculture or horticulture for controlling or preventing infestation of plants, harvested food crops, seeds or non-living materials by phytopathogenic microorganisms, preferably fungi.


The present invention provides a compound of formula I:







wherein

  • R1 is hydrogen, C1-C6alkyl, C1-C6haloalkyl or C3-C6cycloalkyl;
  • R2 is cycloalkyl, cycloalkylalkyl, halocycloalkyl, cycloalkoxy, halocycloalkoxy, cycloalkylalkoxy, halocycloalkylalkoxy, alkoxyalkyl, cycloalkoxyalkoxyalkyl, haloalkoxyalkyl, trialkylsilyl, alkylthioalkyl, haloalkylthioalkyl, cycloalkylthio, halocycloalkylthio, cycloalkylalkylthio, halocycloalkylalkylthio, alkylsulfinylalkyl, alkylsulfonylalkyl, alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, haloalkylsulfonyl, C2-C6alkenyl, C2-C6alkynyl, optionally substituted arylsulfonyl, optionally substituted aryloxy, optionally substituted heteroaryloxy, optionally substituted arylthio, optionally substituted heteroarylthio; or
  • R2 together with an adjacent carbon atom forms an optionally substituted fused ring;
  • R3 is an optionally substituted aryl;
  • R4 is hydrogen, halogen, C1-C6alkyl, C1-C6haloalkyl, C1-C6alkoxy, C1-C6haloalkoxy, hydroxy or cyano; and
  • n is a whole number from 1 to 4;
  • or an agrochemically usable salt form thereof.


When n is 2, 3 or 4, then each R2 independently of each other and independently at each occurrence can be the same or different.


In the above definition aryl includes aromatic hydrocarbon rings like phenyl, naphthyl, anthracenyl, phenanthrenyl and biphenyl, with phenyl being preferred.


Heteroaryl stands for aromatic ring systems comprising mono-, bi- or tricyclic systems wherein at least one oxygen, nitrogen or sulfur atom is present as a ring member. Examples are furyl, thienyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, oxadiazolyl, thiadiazolyl, triazolyl, tetrazolyl, pyridyl, pyridazinyl, pyrimidinyl, pyrazinyl, triazinyl, tetrazinyl, indolyl, benzothiophenyl, benzofuranyl, benzimidazolyl, indazolyl, benzotriazolyl, benzothiazolyl, benzoxazolyl, quinolinyl, isoquinolinyl, phthalazinyl, quinoxalinyl, quinazolinyl, cinnolinyl and naphthyridinyl.


The above or below mentioned fused ring, carbocyclic ring, heterocyclic ring, aryl group and heteroaryl group may be optionally substituted. This means that they may carry one or more identical or different substituents. Normally not more than three substituents are present at the same time. Examples of substituents are: halogen, alkyl, haloalkyl, cycloalkyl, cycloalkylalkyl, alkenyl, haloalkenyl, cycloalkenyl, alkynyl, haloalkynyl, alkyloxy, haloalkyloxy, cycloalkoxy, alkenyloxy, haloalkenyloxy, alkynyloxy, haloalkenyloxy, alkylthio, haloalkylthio, cycloalkylthio, alkenylthio, alkynylthio, alkylcarbonyl, haloalkylcarbonyl, cycloalkylcarbonyl, alkenylcarbonyl, alkynylcarbonyl, alkoxyalkyl, cyano, nitro, hydroxy, mercapto, amino, alkylamino, dialkylamino. Typical examples for optionally substituted aryl include 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-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-cyanophenyl, 2,6-difluoro-4-methylphenyl, 2,6-dichloro-4-methoxyphenyl, 2,6-dichloro-4-trifluoromethoxyphenyl, 2,6-dichloro-4-trifluoromethylphenyl, 2,6-dichloro-4-cyanophenyl, 2,6-dichloro-4-methylphenyl, pentafluorophenyl. Typical examples for optionally substituted heteroaryl include 2-chloro-thiophen-5-yl, 2-bromothiophen-5-yl, 2-methylthiophen-5-yl, 5-chlorothiophen-2-yl, 4-bromo-5-methylthiophen-2-yl, 4-bromothiophen-2-yl, 5-bromothiophen-2-yl, 5-methylthiophen-2-yl, 5-bromofuran-2-yl, 4,5-dimethylfuran-2-yl, 5-methylfuran-2-yl, 5-chlorofuran-2-yl, 3-methylisothiazol-4-yl, 5-methylisoxazol-3-yl, 2-chloropyridin-5-yl, 2-methylpyridin-5-yl, 2-bromopyridin-5-yl, 5-chloropyridin-2-yl, 5-methylpyridin-2-yl, 5-bromopyridin-2-yl, 6-chloropyridin-2-yl, 6-methylpyridin-2-yl, 6-chloropyridin-3-yl, 6-bromopyridin-3-yl, 5-bromopyridin-3-yl, 6-methylpyridin-3-yl, 6-methoxypyridin-3-yl, 5,6-dichloropyridin-3-yl, 2-chloropyridin-4-yl, 2-methylpyridin-4-yl, 2,6-dichloropyridin-4-yl, 2-methylpyrimidin-4-yl.


In the above definition halogen is fluorine, chlorine, bromine or iodine.


The alkyl, alkenyl or alkynyl radicals may be straight-chained or branched.


Alkyl on its own or as part of another substituent is, depending upon the number of carbon atoms mentioned, for example, methyl, ethyl, propyl, butyl, pentyl, hexyl and the isomers thereof, for example, isopropyl, isobutyl, sec-butyl, tert-butyl, isopentyl or tert-pentyl.


A haloalkyl group may contain one or more identical or different halogen atoms and, for example, may stand for CH2Cl, CHCl2, CCl3, CH2F, CHF2, CF3, CF3CH2, CH3CF2, CF3CF2 or CCl3CCl2.


Cycloalkyl on its own or as part of another substituent is, depending upon the number of carbon atoms mentioned, for example, cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl.


Alkenyl on its own or as part of another substituent is, depending upon the number of carbon atoms mentioned, for example, ethenyl, allyl, 1-propenyl, buten-2-yl, buten-3-yl, penten-1-yl, penten-3-yl, hexen-1-yl or 4-methyl-3-pentenyl.


Alkynyl on its own or as part of another substituent is, depending upon the number of carbon atoms mentioned, for example, ethynyl, propyn-1-yl, propyn-2-yl, butyn-1-yl, butyn-2-yl, 1-methyl-2-butynyl, hexyn-1-yl or 1-ethyl-2-butynyl.


The presence of one or more possible asymmetric carbon atoms in a compound of formula I means that the compounds may occur in optically isomeric, that means enantiomeric or diastereomeric forms. As a result of the presence of a possible aliphatic C═C double bond, geometric isomerism, that means cis-trans or (E)-(Z) isomerism may also occur. Also atropisomers may occur as a result of restricted rotation about a single bond. Formula I is intended to include all those possible isomeric forms and mixtures thereof. The present invention intends to include all those possible isomeric forms and mixtures thereof for a compound of formula I.


In each case, the compounds of formula I according to the invention are in free form or in an agronomically usable salt form.


In a first embodiment, compounds of formula I according to the invention have R1 which is hydrogen, C1-C6alkyl or C1-C6haloalkyl.


In a second embodiment, compounds of formula I according to the invention have R2 is cycloalkyl, cycloalkylalkyl, halocycloalkyl, cycloalkoxy, halocycloalkoxy, cycloalkylalkoxy, halocycloalkylalkoxy, alkoxyalkyl, cycloalkoxyalkoxyalkyl, haloalkoxyalkyl, trialkylsilyl, alkylthioalkyl, haloalkylthioalkyl, cycloalkylthio, halocycloalkylthio, cycloalkylalkylthio, halocycloalkylalkylthio, alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, haloalkylsulfonyl, C2-C6alkenyl, C2-C6alkynyl, optionally substituted arylsulfonyl, optionally substituted aryloxy, optionally substituted heteroaryloxy, optionally substituted arylthio, optionally substituted heteroarylthio; or

  • R2 together with an adjacent carbon atom forms an optionally substituted 2- to 7-membered fused ring.


In a third embodiment, compounds of formula I according to the invention have R3 which is an optionally substituted phenyl.


In a fourth embodiment, compounds of formula I according to the invention have R4 which is halogen, C1-C6alkyl, C1-C6haloalkyl, C1-C6alkoxy, C1-C6haloalkoxy, hydroxy or cyano.


In a fifth embodiment, compounds of formula I according to the invention have wherein n is whole number from 1 to 3.


Preferred subgroups of compounds of formula I according to the invention are those wherein R1 is C1-C6alkyl or C1-C6haloalkyl;

  • R2 is cycloalkyl, cycloalkylalkyl, halocycloalkyl, cycloalkoxy, cycloalkylalkoxy, alkoxyalkyl, cycloalkoxyalkoxyalkyl, haloalkoxyalkyl, trialkylsilyl, alkylthioalkyl, haloalkylthioalkyl, cycloalkylthio, halocycloalkylthio, cycloalkylalkylthio, halocycloalkylalkylthio, alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, haloalkylsulfonyl, C2-C6alkenyl, C2-C6alkynyl, optionally substituted arylsulfonyl, optionally substituted aryloxy, optionally substituted heteroaryloxy, optionally substituted arylthio, optionally substituted heteroarylthio; or
  • R2 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;
  • R3 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;
  • R4 is halogen, C1-C6alkyl, C1-C6haloalkyl, C1-C6alkoxy, C1-C6haloalkoxy or hydroxy; and
  • n is a whole number from 1 to 3.


More preferred subgroups of compounds of formula I according to the invention are those wherein

  • R1 is C1-C6alkyl;
  • R2 is cycloalkyl, cycloalkylalkyl, halocycloalkyl, cycloalkoxy, cycloalkylalkoxy, alkoxyalkyl, haloalkoxyalkyl, trialkylsilyl, alkylthioalkyl, haloalkylthioalkyl, cycloalkylthio, cycloalkylalkylthio, halocycloalkylalkylthio, alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, haloalkylsulfonyl, C2-C6alkenyl, C2-C6alkynyl, optionally substituted arylsulfonyl, optionally substituted aryloxy, optionally substituted heteroaryloxy, optionally substituted arylthio, optionally substituted heteroarylthio; or
  • R2 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;
  • R3 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;
  • R4 is halogen, C1-C6alkyl, C1-C6haloalkyl, C1-C6alkoxy or hydroxy;
  • n is a whole number from 1 to 3.


Most preferred subgroups of compounds of formula I according to the invention are those wherein

  • R1 is C1-C3alkyl;
  • R2 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
  • R2 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;
  • R3 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;
  • R4 is halogen, C1-C6alkyl, C1-C6alkoxy or hydroxy; and
  • n is a whole number from 1 to 2.


Especially preferred subgroups of compounds of formula I according to the invention are those wherein

  • R1 is methyl;
  • R2 is cycloalkoxy, cycloalkylalkoxy, alkylsulfonyl, optionally substituted aryloxy; or
  • R2 together with an adjacent carbon atom forms an optionally substituted 6-membered aromatic carbocyclic fused ring;
  • R3 is 2-methylphenyl, 2,6-difluorophenyl, 2-chloro-6-fluorophenyl or 2,4,6-trifluorophenyl;
  • R4 is fluoro, chloro, methyl, methoxy or hydroxy; and
  • n is a whole number from 1 to 2.


Preferred individual compounds are:

  • 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.


Certain pyridazine derivatives with a halogen-, alkyl-, alkoxy-, alkylthio-, nitro- and cyano-substituted phenyl group in position 5 have been proposed for controlling plant-destructive fungi, for example in WO 2005/121104 and WO 2006/001175. However, the action of those preparations is not satisfactory in all aspects of agricultural needs. Surprisingly, with the compounds of formula I, new kinds of fungicides having a high level of biological activity have now been found.


The compounds of formula I.2, wherein R1, R2, R3 and n are as defined for compound of formula I and R5 is C1-C6alkyl or C1-C6haloalkyl, can be obtained by reaction of a compound of formula I.1, wherein R1, R2, R3 and n are as defined for compound of formula I and Hal is halogen, preferably fluorine, chlorine or bromine, with an alcohol R5OH, wherein R5 is C1-C6alkyl or C1-C6haloalkyl, and a base or with a sodium alkoxide NaOR5, wherein R5 is C1-C6alkyl or C1-C6haloalkyl.







The compounds of formula I.3, wherein R1, R2, R3 and n are as defined for compound of formula I and R6 is C1-C6alkyl, can be obtained by transformation of a compound of formula I.1, wherein R1, R2, R3 and n are as defined for compound of formula I and Hal is halogen, preferably chlorine or bromine, with a Grignard reagent R6MgHal, wherein R6 is C1-C6alkyl and Hal is halogen, preferably chlorine or bromine, in the presence of a transition metal catalyst.







The compounds of formula I.4, wherein R1, R2, R3 and n are as defined for compound of formula I, can be obtained by transformation of a compound of formula I.1, wherein R1, R2, R3 and n are as defined for compound of formula I and Hal is halogen, preferably chlorine or bromine, with an inorganic fluoride, e.g. potassium fluoride.







The compounds of formula I.1, wherein R1, R2, R3 and n are as defined for compound of formula I and Hal is halogen, preferably chlorine or bromine, can be obtained by reaction of a compound of formula I.5, wherein R1, R2, R3 and n are as defined for compound of formula I, with a phosphorus oxyhalide, e.g. phosphorus oxychloride or phosphorus oxybromide, or thionyl halide, e.g. thionyl chloride or thionyl bromide.







The compounds of formula I.5, wherein R1, R2, R3 and n are as defined for compound of formula I, can be obtained by reaction of a compound of formula II, wherein R1, R2, R3 and n are as defined for compound of formula I, with a hydrazine derivative, e.g. hydrazine hydrate.







The compounds of formula II, wherein R1, R2, R3 and n are as defined for compound of formula I, can be obtained by oxidation of a compound of formula III, wherein R1, R2, R3 and n are as defined for compound of formula I, with oxygen, air or 3-chloroperbenzoic acid.







The compounds of formula III, wherein R1, R2, R3 and n are as defined for compound of formula I, can be obtained by reaction of a compound of formula IV, wherein R1, R2, R3 and n are as defined for compound of formula I, with a base, e.g. pyridine, triethylamine, diisopropylethylamine, 1,5-diazabicyclo[4.3.0]non-5-ene or 1,8-diazabicyclo[5.4.0]undec-7-ene.







The compounds of formula IV, wherein R1, R2, R3 and n are as defined for compound of formula I, can be obtained by reaction of a compound of formula V, wherein R1, R2 and n are as defined for compound of formula I and Hal is halogen, preferably chlorine or bromine, with a compound of formula VI, wherein R3 is as defined for compound of formula I, and a base, e.g. pyridine, triethylamine, diisopropylethylamine, 1,5-diazabicyclo[4.3.0]non-5-ene or 1,8-diazabicyclo[5.4.0]undec-7-ene.







Surprisingly, it has now been found that the novel compounds of formula I have, for practical purposes, a very advantageous spectrum of activities for protecting plants against diseases that are caused by fungi as well as by bacteria and viruses.


The compounds of formula I can be used in the agricultural sector and related fields of use as active ingredients for controlling plant pests or on non-living materials for control of spoilage microorganisms or organisms potentially harmful to man. The novel compounds are distinguished by excellent activity at low rates of application, by being well tolerated by plants and by being environmentally safe. They have very useful curative, preventive and systemic properties and are used for protecting numerous cultivated plants. The compounds of formula I can be used to inhibit or destroy the pests that occur on plants or parts of plants (fruit, blossoms, leaves, stems, tubers, roots) of different crops of useful plants, while at the same time protecting also those parts of the plants that grow later e.g. from phytopathogenic microorganisms.


It is also possible to use compounds of formula I as dressing agents for the treatment of plant propagation material, e.g., seed, such as fruits, tubers or grains, or plant cuttings (for example rice), for the protection against fungal infections as well as against phytopathogenic fungi occurring in the soil. The propagation material can be treated with a composition comprising a compound of formula I before planting: seed, for example, can be dressed before being sown. The active ingredients according to the invention can also be applied to grains (coating), either by impregnating the seeds in a liquid formulation or by coating them with a solid formulation. The composition can also be applied to the planting site when the propagation material is being planted, for example, to the seed furrow during sowing. The invention relates also to such methods of treating plant propagation material and to the plant propagation material so treated.


Furthermore the compounds according to present invention can be used for controlling fungi in related areas, for example in the protection of technical materials, including wood and wood related technical products, in food storage, in hygiene management.


In addition, the invention could be used to protect non-living materials from fungal attack, e.g. lumber, wall boards and paint.


The compounds of formula I are, for example, effective against the phytopathogenic fungi of the following classes: Fungi imperfecti (e.g. Botrytis spp., Alternaria spp.) and Basidiomycetes (e.g. Rhizoctonia spp., Hemileia spp., Puccinia spp., Phakopsora spp., Ustilago spp., Tilletia spp.). Additionally, they are also effective against Ascomycetes (e.g. Venturia spp., Blumeria spp., Podosphaera leucotricha, Monilinia spp., Fusarium spp., Uncinula spp., Mycosphaerella spp., Pyrenophora spp., Rhynchosporium secalis, Magnaporthe spp., Colletotrichum spp., Gaeumannomyces graminis, Tapesia spp., Ramularia spp., Microdochium nivale, Sclerotinia spp.) and Oomycetes (e.g. Phytophthora spp., Pythium spp., Plasmopara spp., Pseudoperonospora cubensis). Outstanding activity has been observed against powdery mildews (e.g. Uncinula necator), rusts (e.g. Puccinia spp.) and leaf spots (e.g. Septoria tritici). Furthermore, the novel compounds of formula I are effective against phytopathogenic bacteria and viruses (e.g. against Xanthomonas spp, Pseudomonas spp, Erwinia amylovora as well as against the tobacco mosaic virus).


Within the scope of present invention, target crops to be protected typically comprise the following species of plants: cereal (wheat, barley, rye, oat, rice, maize, sorghum and related species); beet (sugar beet and fodder beet); pomes, drupes and soft fruit (apples, pears, plums, peaches, almonds, cherries, strawberries, raspberries and blackberries); leguminous plants (beans, lentils, peas, soybeans); oil plants (rape, mustard, poppy, olives, sunflowers, coconut, castor oil plants, cocoa beans, groundnuts); cucumber plants (pumpkins, cucumbers, melons); fibre plants (cotton, flax, hemp, jute); citrus fruit (oranges, lemons, grapefruit, mandarins); vegetables (spinach, lettuce, asparagus, cabbages, carrots, onions, tomatoes, potatoes, paprika); lauraceae (avocado, cinnamomum, camphor) or plants such as tobacco, nuts, coffee, eggplants, sugar cane, tea, pepper, vines, hops, bananas and natural rubber plants, as well as turf and ornamentals.


The target crops in accordance with the invention include conventional as well as genetically enhanced or engineered varieties such as, for example, insect resistant (e.g. Bt. and VIP varieties) as well as disease resistant, herbicide tolerant (e.g. glyphosate- and glufosinate-resistant maize varieties commercially available under the trade names RoundupReady® and LibertyLink®) and nematode tolerant varieties. By way of example, suitable genetically enhanced or engineered crop varieties include the Stoneville 5599BR cotton and Stoneville 4892BR cotton varieties.


The compounds of formula I are used in unmodified form or, preferably, together with the adjuvants conventionally employed in the art of formulation. To this end they are conveniently formulated in known manner to emulsifiable concentrates, coatable pastes, directly sprayable or dilutable solutions or suspensions, dilute emulsions, wettable powders, soluble powders, dusts, granulates, and also encapsulations e.g. in polymeric substances. As with the type of the compositions, the methods of application, such as spraying, atomising, dusting, scattering, coating or pouring, are chosen in accordance with the intended objectives and the prevailing circumstances. The compositions may also contain further adjuvants such as stabilizers, antifoams, viscosity regulators, binders or tackifiers as well as fertilizers, micronutrient donors or other formulations for obtaining special effects.


Suitable carriers and adjuvants can be solid or liquid and are substances useful in formulation technology, e.g. natural or regenerated mineral substances, solvents, dispersants, wetting agents, tackifiers, thickeners, binders or fertilizers. Such carriers are for example described in WO 97/33890.


The compounds of formula I are normally used in the form of compositions and can be applied to the crop area or plant to be treated, simultaneously or in succession with further compounds. These further compounds can be e.g. fertilizers or micronutrient donors or other preparations, which influence the growth of plants. They can also be selective herbicides or non-selective herbicides as well as insecticides, fungicides, bactericides, nematicides, molluscicides or mixtures of several of these preparations, if desired together with further carriers, surfactants or application promoting adjuvants customarily employed in the art of formulation.


The compounds of formula I are normally used in the form of fungicidal compositions for controlling or protecting against phytopathogenic microorganisms, comprising as active ingredient at least one compound of formula I, in free form or in agrochemically usable salt form, and at least one of the above-mentioned adjuvants.


The compounds of formula I can be mixed with other fungicides, resulting in some cases in unexpected synergistic activities. Mixing components which are particularly preferred are:


Azoles, such as azaconazole, BAY 14120, bitertanol, bromuconazole, cyproconazole, difenoconazole, diniconazole, epoxiconazole, fenbuconazole, fluquinconazole, flusilazole, flutriafol, hexaconazole, imazalil, imibenconazole, ipconazole, metconazole, myclobutanil, pefurazoate, penconazole, prothioconazole, pyrifenox, prochloraz, propiconazole, simeconazole, tebuconazole, tetraconazole, triadimefon, triadimenol, triflumizole, triticonazole;


Pyrimidinyl carbinoles, such as ancymidol, fenarimol, nuarimol;


2-amino-pyrimidines, such as bupirimate, dimethirimol, ethirimol;


Morpholines, such as dodemorph, fenpropidine, fenpropimorph, spiroxamine, tridemorph;


Anilinopyrimidines, such as cyprodinil, mepanipyrim, pyrimethanil;


Pyrroles, such as fenpiclonil, fludioxonil;


Phenylamides, such as benalaxyl, furalaxyl, metalaxyl, R-metalaxyl, ofurace, oxadixyl;


Benzimidazoles, such as benomyl, carbendazim, debacarb, fuberidazole, thiabendazole;


Dicarboximides, such as chiozolinate, dichlozoline, iprodione, myclozoline, procymidone, vinclozoline;


Carboxamides, such as boscalid, carboxin, fenfuram, flutolanil, mepronil, oxycarboxin, penthiopyrad, thifluzamide; guanidines, such as guazatine, dodine, iminoctadine;


Strobilurines, such as azoxystrobin, dimoxystrobin, enestroburin, fluoxastrobin, kresoxim-methyl, metominostrobin, trifloxystrobin, orysastrobin, picoxystrobin, pyraclostrobin;


Dithiocarbamates, such as ferbam, mancozeb, maneb, metiram, propineb, thiram, zineb, ziram;


N-halomethylthiotetrahydrophthalimides, such as captafol, captan, dichlofluanid, fluoromides, folpet, tolyfluanid;


Cu-compounds, such as Bordeaux mixture, copper hydroxide, copper oxychloride, copper sulfate, cuprous oxide, mancopper, oxine-copper;


Nitrophenol-derivatives, such as dinocap, nitrothal-isopropyl;


Organo-phosphorus-derivatives, such as edifenphos, iprobenphos, isoprothiolane, phosdiphen, pyrazophos, toiclofos-methyl;


Pyridazine-derivatives which are known and may be prepared by methods as described in WO 05/121104, WO 06/001175 and WO 07/066601, such as 3-chloro-5-(4-chloro-phenyl)-6-methyl-4-(2,4,6-trifluoro-phenyl)-pyridazine (formula P.1), 3-chloro-6-methyl-5-p-tolyl-4-(2,4,6-trifluoro-phenyl)-pyridazine (formula P.2) and 3-chloro-4-(3-chloro-5-methoxy-pyridin-2-yl)-5-(4-chloro-phenyl)-6-methyl-pyridazine (formula P.3);







Triazolopyrimidine derivatives which are known and may be prepared by methods as described in WO98/46607, such as 5-chloro-7-(4-methyl-piperidin-1-yl)-6-(2,4,6-trifluoro-phenyl)-[1,2,4]triazolo[1,5-a]pyrimidine (formula T.1);







Carboxamide derivatives which are known and may be prepared by methods as described in WO04/035589 and in WO06/37632, such as 3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid (9-isopropyp-1,2,3,4-tetrahydro-1,4-methano-naphthalen-5-yl)-amide (formula U.1); or







N-(3′,4′-dichloro-5-fluoro-1,1′-biphenyl-2-yl)-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide (compound F-13)


Benzamide derivatives which are known and may be prepared by methods as described in WO 2004/016088, such as N-{-2-[3-chloro-5-(trifluoromethyl)-2-pyridinyl]ethyl}-2-trifluoromethylbenzamide, which is also known under the name fluopyram (formula V.1);







and


Various others, such as acibenzolar-S-methyl, anilazine, benthiavalicarb, blasticidin-S, chinomethionate, chloroneb, chlorothalonil, cyflufenamid, cymoxanil, dichlone, diclocymet, diclomezine, dicloran, diethofencarb, dimethomorph, flumorph, dithianon, ethaboxam, etridiazole, famoxadone, fenamidone, fenoxanil, fentin, ferimzone, fluazinam, fluopicolide, flusulfamide, fenhexamid, fosetyl-aluminum, hymexazol, iprovalicarb, cyazofamid, kasugamycin, mandipropamid, methasulfocarb, metrafenone, nicobifen, pencycuron, phthalide, polyoxins, probenazole, propamocarb, proquinazid, pyroquilon, quinoxyfen, quintozene, sulfur, tiadinil, triazoxide, tricyclazole, triforine, validamycin, zoxamide and glyphosate.


Another aspect of invention is related to the use of a compound of formula I, of a composition comprising at least one compound of formula I or of a fungicidal mixture comprising at least one compound of formula I in admixture with other fungicides, as described above, for controlling or preventing infestation of plants, harvested food crops or non-living materials by phytopathogenic microorganisms, preferably fungal organisms.


A further aspect of invention is related to a method of controlling or preventing an infestation of crop plants or of non-living materials by phytopathogenic or spoilage microorganisms or organisms potentially harmful to man, especially fungal organisms, which comprises the application of a compound of formula I as active ingredient to the plants, to parts of the plants or to the locus thereof, or to any part of the non-living materials. Controlling or preventing means reducing the infestation of crop plants or of non-living materials by phytopathogenic or spoilage microorganisms or organisms potentially harmful to man, especially fungal organisms, to such a level that an improvement is demonstrated.


A preferred method of controlling or preventing an infestation of crop plants by phytopathogenic microorganisms, especially fungal organisms, which comprises the application of a compound of formula I, or an agrochemical composition which contains at least one of said compounds, is foliar application. The frequency of application and the rate of application will depend on the risk of infestation by the corresponding pathogen. However, the compounds of formula I can also penetrate the plant through the roots via the soil (systemic action) by drenching the locus of the plant with a liquid formulation, or by applying the compounds in solid form to the soil, e.g. in granular form (soil application). In crops of water rice such granulates can be applied to the flooded rice field. The compounds of formula I may also be applied to seeds (coating) by impregnating the seeds or tubers either with a liquid formulation of the fungicide or coating them with a solid formulation.


A formulation [that is, a composition containing the compound of formula I] and, if desired, a solid or liquid adjuvant or monomers for encapsulating the compound of formula I, is prepared in a known manner, typically by intimately mixing and/or grinding the compound with extenders, for example solvents, solid carriers and, optionally, surface active compounds (surfactants).


The agrochemical formulations will usually contain from 0.1 to 99% by weight, preferably from 0.1 to 95% by weight, of the compound of formula I, 99.9 to 1% by weight, preferably 99.8 to 5% by weight, of a solid or liquid adjuvant, and from 0 to 25% by weight, preferably from 0.1 to 25% by weight, of a surfactant.


Advantageous rates of application are normally from 5 g to 2 kg of active ingredient (a.i.) per hectare (ha), preferably from 10 g to 1 kg a.i./ha, most preferably from 20 g to 600 g a.i./ha. When used as seed drenching agent, convenient dosages are from 10 mg to 1 g of active substance per kg of seeds.


Whereas it is preferred to formulate commercial products as concentrates, the end user will normally use dilute formulations.


The following non-limiting examples illustrate the above-described invention in more detail.







EXAMPLE 1
This Example Illustrates the Preparation of 3-chloro-6-methyl-5-naphthalen-2-yl-4-(2,4,6-trifluorophenyl)-pyridazine (Compound No. I.ae.198)
a) Preparation of 2-bromo-1-naphthalen-2-yl-propan-1-one

Bromine (2.2 ml) is added to the mixture of 1-naphthalen-2-yl-propan-1-one (7.6 g), 0.1 ml of hydrobromic acid (48% solution) and 100 ml of acetic acid at 0° C. under a nitrogen atmosphere. Subsequently, the mixture is stirred for 2.0 h at room temperature. The reaction mixture is evaporated under reduced pressure. After chromatography on silica gel, using a mixture of heptane/ethyl acetate 9:1 as eluent, 2-bromo-1-naphthalen-2-yl-propan-1-one is obtained as a yellow oil.


b) Preparation of 5-hydroxy-5-methyl-4-naphthalen-2-yl-3-(2,4,6-trifluorophenyl)-5H-furan-2-one (Compound No. II.ae.040)

A mixture of 2-bromo-1-naphthalen-2-yl-propan-1-one (3.1 g), 2,4,6-trifluorophenylacetic acid (2.5 g), 1.3 ml of triethylamine and 30 ml of acetonitrile is stirred for 16 h at room temperature. Subsequently 30 ml of acetonitrile and 4.3 ml of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) are added under cooling and stirring is continued for further 3 h. Then air is blown through the reaction mixture for 3 h. An aqueous ammonium chloride solution is added and the mixture is extracted with ethyl acetate. The combined organic layer is washed with a saturated aqueous sodium bicarbonate solution and with brine, dried over sodium sulfate and evaporated under reduced pressure. The remainder is purified by chromatography on silica gel, using a mixture of heptane/ethyl acetate 9:1 as eluent to obtain 5-hydroxy-5-methyl-4-naphthalen-2-yl-3-(2,4,6-trifluorophenyl)-5H-furan-2-one (Compound No. II.ae.040) as colourless crystals, m.p. 164-165° C.


c) Preparation of 6-methyl-5-naphthalen-2-yl-4-(2,4,6-trifluorophenyl)-2H-pyridazin-3-one (Compound No. I.ae.196)

A mixture of 5-hydroxy-5-methyl-4-naphthalen-2-yl-3-(2,4,6-trifluorophenyl)-5H-furan-2-one (Compound No. II.ae.040, 2.8 g), 0.4 ml of hydrazine hydrate and 30 ml of 1-butanol is heated for 16 h to 120° C. Subsequently, the mixture is cooled to 0° C. The hereby obtained solid is filtered and washed with hexane to obtain 6-methyl-5-naphthalen-2-yl-4-(2,4,6-trifluorophenyl)-2H-pyridazin-3-one (Compound No. I.ae.196) as colourless crystals, m.p. 266-268° C.


d) A mixture of 6-methyl-5-naphthalen-2-yl-4-(2,4,6-trifluorophenyl)-2H-pyridazin-3-one (Compound No. I.ae.196, 1.8 g) and 7.0 ml of phosphorus oxychloride are mixed and heated at 110° C. for 1 h. After cooling the reaction mixture is evaporated under reduced pressure. The remainder is taken up with ethyl acetate and water and the phases are separated. The organic layer is washed with water and brine, dried over sodium sulfate and evaporated under reduced pressure. The residue is purified by chromatography on silica gel, using a mixture of heptane/ethyl acetate 9:1 as eluent, to deliver 3-chloro-6-methyl-5-naphthalen-2-yl-4-(2,4,6-trifluorophenyl)-pyridazine (Compound No. I.ae.198) as beige crystals (from diethyl ether/hexane), m.p. 86-89° C.


EXAMPLE 2
This Example Illustrates the Preparation of 3-methoxy-6-methyl-5-naphthalen-2-yl-4-(2,4,6-trifluorophenyl)-pyridazine (Compound No. I.ae.199) and 4-(2,6-difluoro-4-methoxyphenyl)-3-methoxy-6-methyl-5-naphthalen-2-yl-pyridazine (Compound No. I.ae.254)

A mixture of 3-chloro-6-methyl-5-naphthalen-2-y-4-(2,4,6-trifluorophenyl)-pyridazine (Compound No. I.ae.198, 0.9 g), sodium methoxide (30% solution in methanol, 0.7 g) and 10 ml of methanol is heated for 16 h to 60° C. Subsequently the reaction mixture is cooled, diluted with water and extracted with ethyl acetate. The combined organic layer is washed with water and brine, dried over sodium sulfate and evaporated under reduced pressure. The remainder is purified by chromatography on silica gel, using a mixture of hexane/tert.butyl methyl ether 4:1 as eluent to obtain 3-methoxy-6-methyl-5-naphthalen-2-yl-4-(2,4,6-trifluorophenyl)-pyridazine (Compound I.ae.199) as colourless crystals, m.p. 138-140° C. and 4-(2,6-difluoro-4-methoxyphenyl)-3-methoxy-6-methyl-5-naphthalen-2-yl-pyridazine (Compound I.ae.254) as a foam.


EXAMPLE 3
This Example Illustrates the Preparation of 3-fluoro-6-methyl-5-naphthalen-2-yl-4-(2,4,6-trifluorophenyl)-pyridazine (Compound No. I.ae.197)

A mixture of 3-chloro-6-methyl-5-naphthalen-2-yl-4-(2,4,6-trifluorophenyl)-pyridazine (Compound No. I.ae.198, 0.5 g), potassium fluoride (0.2 g) and 8 ml of dimethyl sulfoxide are mixed and heated to 140° C. for 72 h. Subsequently the reaction mixture is cooled, diluted with water and extracted with ethyl acetate. The combined organic layer is washed with water and brine, dried over sodium sulfate and evaporated under reduced pressure. The remainder is purified by chromatography on silica gel, using a mixture of hexane/ethyl acetate 9:1 as eluent to obtain 3-fluoro-6-methyl-5-naphthalen-2-yl-4-(2,4,6-trifluorophenyl)-pyridazine (Compound No. I.ae.197) as colourless crystals (from diethyl ether/hexane), m.p. 108-110° C.


EXAMPLE 4
This Example Illustrates the Preparation of 3,6-dimethyl-4-naphthalen-2-yl-5-(2,4,6-trifluorophenyl)-pyridazine (Compound No. I.ae.200)

1.5 ml of a 3 M solution of methylmagnesium bromide in diethyl ether is added slowly to a solution of 3-chloro-6-methyl-5-naphthalen-2-yl-4-(2,4,6-trifluorophenyl)-pyridazine (Compound No. I.ae.198, 0.3 g) and iron(III) acetylacetonate (0.03 g) in 10 ml of tetrahydrofuran and 1.5 ml of 1-methyl-2-pyrrolidinone (NMP) at room temperature. This mixture is stirred for 1.5 h at room temperature. The reaction is quenched with dilute HCl and the aqueous phase is extracted with tert-butyl methyl ether. The combined organic layer is dried over sodium sulfate and evaporated under reduced pressure. The residue is purified by chromatography on silica gel, using a mixture of hexane/ethyl acetate 3:1 as eluent to give 3,6 dimethyl-4-naphthalen-2-yl-5-(2,4,6-trifluorophenyl)-pyridazine (Compound No. I.ae.200) as an oil.


Tables 1 and 2 below illustrate examples of individual compounds of formula I and formula II according to the invention.









TABLE 1







individual compounds of formula I according to the invention










Compound





No.
R1
R3
R4





001
CH3
2-fluorophenyl
OH


002
CH3
2-fluorophenyl
F


003
CH3
2-fluorophenyl
Cl


004
CH3
2-fluorophenyl
OCH3


005
CH3
2-fluorophenyl
CH3


006
CH3
2-chlorophenyl
OH


007
CH3
2-chlorophenyl
F


008
CH3
2-chlorophenyl
Cl


009
CH3
2-chlorophenyl
OCH3


010
CH3
2-chlorophenyl
CH3


011
CH3
2-trifluoromethylphenyl
OH


012
CH3
2-trifluoromethylphenyl
F


013
CH3
2-trifluoromethylphenyl
Cl


014
CH3
2-trifluoromethylphenyl
OCH3


015
CH3
2-trifluoromethylphenyl
CH3


016
CH3
2-methylphenyl
OH


017
CH3
2-methylphenyl
F


018
CH3
2-methylphenyl
Cl


019
CH3
2-methylphenyl
OCH3


020
CH3
2-methylphenyl
CH3


021
CH3
2,3-difluorophenyl
OH


022
CH3
2,3-difluorophenyl
F


023
CH3
2,3-difluorophenyl
Cl


024
CH3
2,3-difluorophenyl
OCH3


025
CH3
2,3-difluorophenyl
CH3


026
CH3
2,4-difluorophenyl
OH


027
CH3
2,4-difluorophenyl
F


028
CH3
2,4-difluorophenyl
Cl


029
CH3
2,4-difluorophenyl
OCH3


030
CH3
2,4-difluorophenyl
CH3


031
CH3
2,5-difluorophenyl
OH


032
CH3
2,5-difluorophenyl
F


033
CH3
2,5-difluorophenyl
Cl


034
CH3
2,5-difluorophenyl
OCH3


035
CH3
2,5-difluorophenyl
CH3


036
CH3
2,6-difluorophenyl
OH


037
CH3
2,6-difluorophenyl
F


038
CH3
2,6-difluorophenyl
Cl


039
CH3
2,6-difluorophenyl
OCH3


040
CH3
2,6-difluorophenyl
CH3


041
CH3
2,3-dichlorophenyl
OH


042
CH3
2,3-dichlorophenyl
F


043
CH3
2,3-dichlorophenyl
Cl


044
CH3
2,3-dichlorophenyl
OCH3


045
CH3
2,3-dichlorophenyl
CH3


046
CH3
2,4-dichlorophenyl
OH


047
CH3
2,4-dichlorophenyl
F


048
CH3
2,4-dichlorophenyl
Cl


049
CH3
2,4-dichlorophenyl
OCH3


050
CH3
2,4-dichlorophenyl
CH3


051
CH3
2,5-dichlorophenyl
OH


052
CH3
2,5-dichlorophenyl
F


053
CH3
2,5-dichlorophenyl
Cl


054
CH3
2,5-dichlorophenyl
OCH3


055
CH3
2,5-dichlorophenyl
CH3


056
CH3
2,6-dichlorophenyl
OH


057
CH3
2,6-dichlorophenyl
F


058
CH3
2,6-dichlorophenyl
Cl


059
CH3
2,6-dichlorophenyl
OCH3


060
CH3
2,6-dichlorophenyl
CH3


061
CH3
2-chloro-3-fluorophenyl
OH


062
CH3
2-chloro-3-fluorophenyl
F


063
CH3
2-chloro-3-fluorophenyl
Cl


064
CH3
2-chloro-3-fluorophenyl
OCH3


065
CH3
2-chloro-3-fluorophenyl
CH3


066
CH3
2-chloro-4-fluorophenyl
OH


067
CH3
2-chloro-4-fluorophenyl
F


068
CH3
2-chloro-4-fluorophenyl
Cl


069
CH3
2-chloro-4-fluorophenyl
OCH3


070
CH3
2-chloro-4-fluorophenyl
CH3


071
CH3
2-chloro-5-fluorophenyl
OH


072
CH3
2-chloro-5-fluorophenyl
F


073
CH3
2-chloro-5-fluorophenyl
Cl


074
CH3
2-chloro-5-fluorophenyl
OCH3


075
CH3
2-chloro-5-fluorophenyl
CH3


076
CH3
2-chloro-6-fluorophenyl
OH


077
CH3
2-chloro-6-fluorophenyl
F


078
CH3
2-chloro-6-fluorophenyl
Cl


079
CH3
2-chloro-6-fluorophenyl
OCH3


080
CH3
2-chloro-6-fluorophenyl
CH3


081
CH3
3-chloro-2-fluorophenyl
OH


082
CH3
3-chloro-2-fluorophenyl
F


083
CH3
3-chloro-2-fluorophenyl
Cl


084
CH3
3-chloro-2-fluorophenyl
OCH3


085
CH3
3-chloro-2-fluorophenyl
CH3


086
CH3
4-chloro-2-fluorophenyl
OH


087
CH3
4-chloro-2-fluorophenyl
F


088
CH3
4-chloro-2-fluorophenyl
Cl


089
CH3
4-chloro-2-fluorophenyl
OCH3


090
CH3
4-chloro-2-fluorophenyl
CH3


091
CH3
5-chloro-2-fluorophenyl
OH


092
CH3
5-chloro-2-fluorophenyl
F


093
CH3
5-chloro-2-fluorophenyl
Cl


094
CH3
5-chloro-2-fluorophenyl
OCH3


095
CH3
5-chloro-2-fluorophenyl
CH3


096
CH3
2-fluoro-3-trifluoromethylphenyl
OH


097
CH3
2-fluoro-3-trifluoromethylphenyl
F


098
CH3
2-fluoro-3-trifluoromethylphenyl
Cl


099
CH3
2-fluoro-3-trifluoromethylphenyl
OCH3


100
CH3
2-fluoro-3-trifluoromethylphenyl
CH3


101
CH3
2-fluoro-4-trifluoromethylphenyl
OH


102
CH3
2-fluoro-4-trifluoromethylphenyl
F


103
CH3
2-fluoro-4-trifluoromethylphenyl
Cl


104
CH3
2-fluoro-4-trifluoromethylphenyl
OCH3


105
CH3
2-fluoro-4-trifluoromethylphenyl
CH3


106
CH3
2-fluoro-5-trifluoromethylphenyl
OH


107
CH3
2-fluoro-5-trifluoromethylphenyl
F


108
CH3
2-fluoro-5-trifluoromethylphenyl
Cl


109
CH3
2-fluoro-5-trifluoromethylphenyl
OCH3


110
CH3
2-fluoro-5-trifluoromethylphenyl
CH3


111
CH3
2-fluoro-6-trifluoromethylphenyl
OH


112
CH3
2-fluoro-6-trifluoromethylphenyl
F


113
CH3
2-fluoro-6-trifluoromethylphenyl
Cl


114
CH3
2-fluoro-6-trifluoromethylphenyl
OCH3


115
CH3
2-fluoro-6-trifluoromethylphenyl
CH3


116
CH3
2-chloro-3-trifluoromethylphenyl
OH


117
CH3
2-chloro-3-trifluoromethylphenyl
F


118
CH3
2-chloro-3-trifluoromethylphenyl
Cl


119
CH3
2-chloro-3-trifluoromethylphenyl
OCH3


120
CH3
2-chloro-3-trifluoromethylphenyl
CH3


121
CH3
2-chloro-4-trifluoromethylphenyl
OH


122
CH3
2-chloro-4-trifluoromethylphenyl
F


123
CH3
2-chloro-4-trifluoromethylphenyl
Cl


124
CH3
2-chloro-4-trifluoromethylphenyl
OCH3


125
CH3
2-chloro-4-trifluoromethylphenyl
CH3


126
CH3
2-chloro-5-trifluoromethylphenyl
OH


127
CH3
2-chloro-5-trifluoromethylphenyl
F


128
CH3
2-chloro-5-trifluoromethylphenyl
Cl


129
CH3
2-chloro-5-trifluoromethylphenyl
OCH3


130
CH3
2-chloro-5-trifluoromethylphenyl
CH3


131
CH3
2-chloro-6-trifluoromethylphenyl
OH


132
CH3
2-chloro-6-trifluoromethylphenyl
F


133
CH3
2-chloro-6-trifluoromethylphenyl
Cl


134
CH3
2-chloro-6-trifluoromethylphenyl
OCH3


135
CH3
2-chloro-6-trifluoromethylphenyl
CH3


136
CH3
4-fluoro-2-trifluoromethylphenyl
OH


137
CH3
4-fluoro-2-trifluoromethylphenyl
F


138
CH3
4-fluoro-2-trifluoromethylphenyl
Cl


139
CH3
4-fluoro-2-trifluoromethylphenyl
OCH3


140
CH3
4-fluoro-2-trifluoromethylphenyl
CH3


141
CH3
4-chloro-2-trifluoromethylphenyl
OH


142
CH3
4-chloro-2-trifluoromethylphenyl
F


143
CH3
4-chloro-2-trifluoromethylphenyl
Cl


144
CH3
4-chloro-2-trifluoromethylphenyl
OCH3


145
CH3
4-chloro-2-trifluoromethylphenyl
CH3


146
CH3
2-fluoro-3-methylphenyl
OH


147
CH3
2-fluoro-3-methylphenyl
F


148
CH3
2-fluoro-3-methylphenyl
Cl


149
CH3
2-fluoro-3-methylphenyl
OCH3


150
CH3
2-fluoro-3-methylphenyl
CH3


151
CH3
2-fluoro-4-methylphenyl
OH


152
CH3
2-fluoro-4-methylphenyl
F


153
CH3
2-fluoro-4-methylphenyl
Cl


154
CH3
2-fluoro-4-methylphenyl
OCH3


155
CH3
2-fluoro-4-methylphenyl
CH3


156
CH3
2-fluoro-5-methylphenyl
OH


157
CH3
2-fluoro-5-methylphenyl
F


158
CH3
2-fluoro-5-methylphenyl
Cl


159
CH3
2-fluoro-5-methylphenyl
OCH3


160
CH3
2-fluoro-5-methylphenyl
CH3


161
CH3
2-fluoro-6-methylphenyl
OH


162
CH3
2-fluoro-6-methylphenyl
F


163
CH3
2-fluoro-6-methylphenyl
Cl


164
CH3
2-fluoro-6-methylphenyl
OCH3


165
CH3
2-fluoro-6-methylphenyl
CH3


166
CH3
2-chloro-3-methylphenyl
OH


167
CH3
2-chloro-3-methylphenyl
F


168
CH3
2-chloro-3-methylphenyl
Cl


169
CH3
2-chloro-3-methylphenyl
OCH3


170
CH3
2-chloro-3-methylphenyl
CH3


171
CH3
2-chloro-4-methylphenyl
OH


172
CH3
2-chloro-4-methylphenyl
F


173
CH3
2-chloro-4-methylphenyl
Cl


174
CH3
2-chloro-4-methylphenyl
OCH3


175
CH3
2-chloro-4-methylphenyl
CH3


176
CH3
2-chloro-5-methylphenyl
OH


177
CH3
2-chloro-5-methylphenyl
F


178
CH3
2-chloro-5-methylphenyl
Cl


179
CH3
2-chloro-5-methylphenyl
OCH3


180
CH3
2-chloro-5-methylphenyl
CH3


181
CH3
2-chloro-6-methylphenyl
OH


182
CH3
2-chloro-6-methylphenyl
F


183
CH3
2-chloro-6-methylphenyl
Cl


184
CH3
2-chloro-6-methylphenyl
OCH3


185
CH3
2-chloro-6-methylphenyl
CH3


186
CH3
4-fluoro-2-methylphenyl
OH


187
CH3
4-fluoro-2-methylphenyl
F


188
CH3
4-fluoro-2-methylphenyl
Cl


189
CH3
4-fluoro-2-methylphenyl
OCH3


190
CH3
4-fluoro-2-methylphenyl
CH3


191
CH3
4-chloro-2-methylphenyl
OH


192
CH3
4-chloro-2-methylphenyl
F


193
CH3
4-chloro-2-methylphenyl
Cl


194
CH3
4-chloro-2-methylphenyl
OCH3


195
CH3
4-chloro-2-methylphenyl
CH3


196
CH3
2,4,6-trifluorophenyl
OH


197
CH3
2,4,6-trifluorophenyl
F


198
CH3
2,4,6-trifluorophenyl
Cl


199
CH3
2,4,6-trifluorophenyl
OCH3


200
CH3
2,4,6-trifluorophenyl
CH3


201
CH3
2,3,6-trifluorophenyl
OH


202
CH3
2,3,6-trifluorophenyl
F


203
CH3
2,3,6-trifluorophenyl
Cl


204
CH3
2,3,6-trifluorophenyl
OCH3


205
CH3
2,3,6-trifluorophenyl
CH3


206
CH3
2,3,4-trifluorophenyl
OH


207
CH3
2,3,4-trifluorophenyl
F


208
CH3
2,3,4-trifluorophenyl
Cl


209
CH3
2,3,4-trifluorophenyl
OCH3


210
CH3
2,3,4-trifluorophenyl
CH3


211
CH3
2,4,6-trichlorophenyl
OH


212
CH3
2,4,6-trichlorophenyl
F


213
CH3
2,4,6-trichlorophenyl
Cl


214
CH3
2,4,6-trichlorophenyl
OCH3


215
CH3
2,4,6-trichlorophenyl
CH3


216
CH3
2,3,6-trichlorophenyl
OH


217
CH3
2,3,6-trichlorophenyl
F


218
CH3
2,3,6-trichlorophenyl
Cl


219
CH3
2,3,6-trichlorophenyl
OCH3


220
CH3
2,3,6-trichlorophenyl
CH3


221
CH3
2,3,4-trichlorophenyl
OH


222
CH3
2,3,4-trichlorophenyl
F


223
CH3
2,3,4-trichlorophenyl
Cl


224
CH3
2,3,4-trichlorophenyl
OCH3


225
CH3
2,3,4-trichlorophenyl
CH3


226
CH3
2,6-difluoro-4-methoxyphenyl
OH


227
CH3
2,6-difluoro-4-methoxyphenyl
F


228
CH3
2,6-difluoro-4-methoxyphenyl
Cl


229
CH3
2,6-difluoro-4-methoxyphenyl
OCH3


230
CH3
2,6-difluoro-4-methoxyphenyl
CH3


231
CH3
2,6-difluoro-4-trifluoromethoxyphenyl
OH


232
CH3
2,6-difluoro-4-trifluoromethoxyphenyl
F


233
CH3
2,6-difluoro-4-trifluoromethoxyphenyl
Cl


234
CH3
2,6-difluoro-4-trifluoromethoxyphenyl
OCH3


235
CH3
2,6-difluoro-4-trifluoromethoxyphenyl
CH3


236
CH3
2,6-difluoro-4-trifluoromethylphenyl
OH


237
CH3
2,6-difluoro-4-trifluoromethylphenyl
F


238
CH3
2,6-difluoro-4-trifluoromethylphenyl
Cl


239
CH3
2,6-difluoro-4-trifluoromethylphenyl
OCH3


240
CH3
2,6-difluoro-4-trifluoromethylphenyl
CH3


241
CH3
2,6-difluoro-4-cyanoyphenyl
OH


242
CH3
2,6-difluoro-4-cyanoyphenyl
F


243
CH3
2,6-difluoro-4-cyanophenyl
Cl


244
CH3
2,6-difluoro-4-cyanophenyl
OCH3


245
CH3
2,6-difluoro-4-cyanophenyl
CH3


246
CH3
2,6-difluoro-4-methylphenyl
OH


247
CH3
2,6-difluoro-4-methylphenyl
F


248
CH3
2,6-difluoro-4-methylphenyl
Cl


249
CH3
2,6-difluoro-4-methylphenyl
OCH3


250
CH3
2,6-difluoro-4-methylphenyl
CH3


251
CH3
2,6-dichloro-4-methoxyphenyl
OH


252
CH3
2,6-dichloro-4-methoxyphenyl
F


253
CH3
2,6-dichloro-4-methoxyphenyl
Cl


254
CH3
2,6-dichloro-4-methoxyphenyl
OCH3


255
CH3
2,6-dichloro-4-methoxyphenyl
CH3


256
CH3
2,6-dichloro-4-trifluoromethoxyphenyl
OH


257
CH3
2,6-dichloro-4-trifluoromethoxyphenyl
F


258
CH3
2,6-dichloro-4-trifluoromethoxyphenyl
Cl


259
CH3
2,6-dichloro-4-trifluoromethoxyphenyl
OCH3


260
CH3
2,6-dichloro-4-trifluoromethoxyphenyl
CH3


261
CH3
2,6-dichloro-4-trifluoromethylphenyl
OH


262
CH3
2,6-dichloro-4-trifluoromethylphenyl
F


263
CH3
2,6-dichloro-4-trifluoromethylphenyl
Cl


264
CH3
2,6-dichloro-4-trifluoromethylphenyl
OCH3


265
CH3
2,6-dichloro-4-trifluoromethylphenyl
CH3


266
CH3
2,6-dichloro-4-cyanophenyl
OH


267
CH3
2,6-dichloro-4-cyanophenyl
F


268
CH3
2,6-dichloro-4-cyanophenyl
Cl


269
CH3
2,6-dichloro-4-cyanophenyl
OCH3


270
CH3
2,6-dichloro-4-cyanophenyl
CH3


271
CH3
2,6-dichloro-4-methylphenyl
OH


272
CH3
2,6-dichloro-4-methylphenyl
F


273
CH3
2,6-dichloro-4-methylphenyl
Cl


274
CH3
2,6-dichloro-4-methylphenyl
OCH3


275
CH3
2,6-dichloro-4-methylphenyl
CH3


276
CH3
pentafluorophenyl
OH


277
CH3
pentafluorophenyl
F


278
CH3
pentafluorophenyl
Cl


279
CH3
pentafluorophenyl
OCH3


280
CH3
pentafluorophenyl
CH3










where
  • a) 280 compounds of formula (I.a):







wherein R1, R3 and R4 are as defined in Table 1.

  • b) 280 compounds of formula (I.b):







wherein R1, R3 and R4 are as defined in Table 1.

  • c) 280 compounds of formula (I.c):







wherein R1, R3 and R4 are as defined in Table 1.

  • d) 280 compounds of formula (I.d):







wherein R1, R3 and R4 are as defined in Table 1.

  • e) 280 compounds of formula (I.e):







wherein R1, R3 and R4 are as defined in Table 1.

  • f) 280 compounds of formula (I.f):







wherein R1, R3 and R4 are as defined in Table 1.

  • g) 280 compounds of formula (I.g):







wherein R1, R3 and R4 are as defined in Table 1.

  • h) 280 compounds of formula (I.h):







wherein R1, R3 and R4 are as defined in Table 1.

  • i) 280 compounds of formula (I.i):







wherein R1, R3 and R4 are as defined in Table 1.

  • j) 280 compounds of formula (I.j):







wherein R1, R3 and R4 are as defined in Table 1.

  • k) 280 compounds of formula (I.k):







wherein R1, R3 and R4 are as defined in Table 1.

  • l) 280 compounds of formula (I.l):







wherein R1, R3 and R4 are as defined in Table 1.

  • m) 280 compounds of formula (I.m):







wherein R1, R3 and R4 are as defined in Table 1.

  • n) 280 compounds of formula (I.n):







wherein R1, R3 and R4 are as defined in Table 1.

  • o) 280 compounds of formula (I.o):







wherein R1, R3 and R4 are as defined in Table 1.

  • p) 280 compounds of formula (I.p):







wherein R1, R3 and R4 are as defined in Table 1.

  • q) 280 compounds of formula (I.q):







wherein R1, R3 and R4 are as defined in Table 1.

  • r) 280 compounds of formula (I.r):







wherein R1, R3 and R4 are as defined in Table 1.

  • s) 280 compounds of formula (I.s):







wherein R1, R3 and R4 are as defined in Table 1.

  • t) 280 compounds of formula (I.t):







wherein R1, R3 and R4 are as defined in Table 1.

  • u) 280 compounds of formula (I.u):







wherein R1, R3 and R4 are as defined in Table 1.

  • v) 280 compounds of formula (I.v):







wherein R1, R3 and R4 are as defined in Table 1.

  • w) 280 compounds of formula (I.w):







wherein R1, R3 and R4 are as defined in Table 1.

  • x) 280 compounds of formula (I.x):







wherein R1, R3 and R4 are as defined in Table 1.

  • y) 280 compounds of formula (I.y):







wherein R1, R3 and R4 are as defined in Table 1.

  • z) 280 compounds of formula (I.z):







wherein R1, R3 and R4 are as defined in Table 1.

  • aa) 280 compounds of formula (I.aa):







wherein R1, R3 and R4 are as defined in Table 1.

  • ab) 280 compounds of formula (I.ab):







wherein R1, R3 and R4 are as defined in Table 1.

  • ac) 280 compounds of formula (I.ac):







wherein R1, R3 and R4 are as defined in Table 1.

  • ad) 280 compounds of formula (I.ad):







wherein R1, R3 and R4 are as defined in Table 1.

  • ae) 280 compounds of formula (I.ae):







wherein R1, R3 and R4 are as defined in Table 1.

  • af) 280 compounds of formula (I.af):







wherein R1, R3 and R4 are as defined in Table 1.

  • ag) 280 compounds of formula (I.ag):







wherein R1, R3 and R4 are as defined in Table 1.

  • ah) 280 compounds of formula (I.ah):







wherein R1, R3 and R4 are as defined in Table 1.

  • ai) 280 compounds of formula (I.ai):







wherein R1, R3 and R4 are as defined in Table 1.

  • aj) 280 compounds of formula (I.aj):







wherein R1, R3 and R4 are as defined in Table 1.

  • ak) 280 compounds of formula (I.ak):







wherein R1, R3 and R4 are as defined in Table 1.

  • al) 280 compounds of formula (I.al):







wherein R1, R3 and R4 are as defined in Table 1.

  • am) 280 compounds of formula (I.am):







wherein R1, R3 and R4 are as defined in Table 1.

  • an) 280 compounds of formula (I.an):







wherein R1, R3 and R4 are as defined in Table 1.

  • ao) 280 compounds of formula (I.ao):







wherein R1, R3 and R4 are as defined in Table 1.

  • ap) 280 compounds of formula (I.ap):







wherein R1, R3 and R4 are as defined in Table 1.

  • aq) 280 compounds of formula (I.aq):







wherein R1, R3 and R4 are as defined in Table 1.

  • ar) 280 compounds of formula (I.ar):







wherein R1, R3 and R4 are as defined in Table 1.

  • as) 280 compounds of formula (I.as):







wherein R1, R3 and R4 are as defined in Table 1.

  • at) 280 compounds of formula (I.at):







wherein R1, R3 and R4 are as defined in Table 1.

  • au) 280 compounds of formula (I.au):







wherein R1, R3 and R4 are as defined in Table 1.

  • av) 280 compounds of formula (I.av):







wherein R1, R3 and R4 are as defined in Table 1.

  • aw) 280 compounds of formula (I.aw):







wherein R1, R3 and R4 are as defined in Table 1.

  • ax) 280 compounds of formula (I.ax):







wherein R1, R3 and R4 are as defined in Table 1.

  • ay) 280 compounds of formula (I.ay):







wherein R1, R3 and R4 are as defined in Table 1.

  • az) 280 compounds of formula (I.az):







wherein R1, R3 and R4 are as defined in Table 1.









TABLE 2







individual compounds of formula II according to the invention









Compound




No.
R1
R3





001
CH3
2-fluorophenyl


002
CH3
2-chlorophenyl


003
CH3
2-trifluoromethylphenyl


004
CH3
2-methylphenyl


005
CH3
2,3-difluorophenyl


006
CH3
2,4-difluorophenyl


007
CH3
2,5-difluorophenyl


008
CH3
2,6-difluorophenyl


009
CH3
2,3-dichlorophenyl


010
CH3
2,4-dichlorophenyl


011
CH3
2,5-dichlorophenyl


012
CH3
2,6-dichlorophenyl


013
CH3
2-chloro-3-fluorophenyl


014
CH3
2-chloro-4-fluorophenyl


015
CH3
2-chloro-5-fluorophenyl


016
CH3
2-chloro-6-fluorophenyl


017
CH3
3-chloro-2-fluorophenyl


018
CH3
4-chloro-2-fluorophenyl


019
CH3
5-chloro-2-fluorophenyl


020
CH3
2-fluoro-3-trifluoromethylphenyl


021
CH3
2-fluoro-4-trifluoromethylphenyl


022
CH3
2-fluoro-5-trifluoromethylphenyl


023
CH3
2-fluoro-6-trifluoromethylphenyl


024
CH3
2-chloro-3-trifluoromethylphenyl


025
CH3
2-chloro-4-trifluoromethylphenyl


026
CH3
2-chloro-5-trifluoromethylphenyl


027
CH3
2-chloro-6-trifluoromethylphenyl


028
CH3
4-fluoro-2-trifluoromethylphenyl


029
CH3
4-chloro-2-trifluoromethylphenyl


030
CH3
2-fluoro-3-methylphenyl


031
CH3
2-fluoro-4-methylphenyl


032
CH3
2-fluoro-5-methylphenyl


033
CH3
2-fluoro-6-methylphenyl


034
CH3
2-chloro-3-methylphenyl


035
CH3
2-chloro-4-methylphenyl


036
CH3
2-chloro-5-methylphenyl


037
CH3
2-chloro-6-methylphenyl


038
CH3
4-fluoro-2-methylphenyl


039
CH3
4-chloro-2-methylphenyl


040
CH3
2,4,6-trifluorophenyl


041
CH3
2,3,6-trifluorophenyl


042
CH3
2,3,4-trifluorophenyl


043
CH3
2,4,6-trichlorophenyl


044
CH3
2,3,6-trichlorophenyl


045
CH3
2,3,4-trichlorophenyl


046
CH3
2,6-difluoro-4-methoxyphenyl


047
CH3
2,6-difluoro-4-trifluoromethoxyphenyl


048
CH3
2,6-difluoro-4-trifluoromethylphenyl


049
CH3
2,6-difluoro-4-cyanoyphenyl


050
CH3
2,6-difluoro-4-methylphenyl


051
CH3
2,6-dichloro-4-methoxyphenyl


052
CH3
2,6-dichloro-4-trifluoromethoxyphenyl


053
CH3
2,6-dichloro-4-trifluoromethylphenyl


054
CH3
2,6-dichloro-4-cyanophenyl


055
CH3
2,6-dichloro-4-methylphenyl


056
CH3
pentafluorophenyl










where
  • a) 56 compounds of formula (II.a):







wherein R1 and R3 are as defined in Table 2.

  • b) 56 compounds of formula (II.b):







wherein R1 and R3 are as defined in Table 2.

  • c) 56 compounds of formula (II.c):







wherein R1 and R3 are as defined in Table 2.

  • d) 56 compounds of formula (II.d):







wherein R1 and R3 are as defined in Table 2.

  • e) 56 compounds of formula (II.e):







wherein R1 and R3 are as defined in Table 2.

  • f) 56 compounds of formula (II.f):







wherein R1 and R3 are as defined in Table 2.

  • g) 56 compounds of formula (II.g):







wherein R1 and R3 are as defined in Table 2.

  • h) 56 compounds of formula (II.h):







wherein R1 and R3 are as defined in Table 2.

  • i) 56 compounds of formula (II.i):







wherein R1 and R3 are as defined in Table 2.

  • j) 56 compounds of formula (II.j):







wherein R1 and R3 are as defined in Table 2.

  • k) 56 compounds of formula (II.k):







wherein R1 and R3 are as defined in Table 2.

  • l) 56 compounds of formula (II.l):







wherein R1 and R3 are as defined in Table 2.

  • m) 56 compounds of formula (II.m):







wherein R1 and R3 are as defined in Table 2.

  • n) 56 compounds of formula (II.n):







wherein R1 and R3 are as defined in Table 2.

  • o) 56 compounds of formula (II.o):







wherein R1 and R3 are as defined in Table 2.

  • p) 56 compounds of formula (II.p):







wherein R1 and R3 are as defined in Table 2.

  • q) 56 compounds of formula (II.q):







wherein R1 and R3 are as defined in Table 2.

  • r) 56 compounds of formula (II.r):







wherein R1 and R3 are as defined in Table 2.

  • s) 56 compounds of formula (II.s):







wherein R1 and R3 are as defined in Table 2.

  • t) 56 compounds of formula (II.t):







wherein R1 and R3 are as defined in Table 2.

  • u) 56 compounds of formula (II.u):







wherein R1 and R3 are as defined in Table 2.

  • v) 56 compounds of formula (II.v):







wherein R1 and R3 are as defined in Table 2.

  • w) 56 compounds of formula (II.w):







wherein R1 and R3 are as defined in Table 2.

  • x) 56 compounds of formula (II.x):







wherein R1 and R3 are as defined in Table 2.

  • y) 56 compounds of formula (II.y):







wherein R1 and R3 are as defined in Table 2.

  • z) 56 compounds of formula (II.z):







wherein R1 and R3 are as defined in Table 2.

  • aa) 56 compounds of formula (II.aa):







wherein R1 and R3 are as defined in Table 2.

  • ab) 56 compounds of formula (II.ab):







wherein R1 and R3 are as defined in Table 2.

  • ac) 56 compounds of formula (II.ac):







wherein R1 and R3 are as defined in Table 2.

  • ad) 56 compounds of formula (II.ad):







wherein R1 and R3 are as defined in Table 2.

  • ae) 56 compounds of formula (II.ae):







wherein R1 and R3 are as defined in Table 2.

  • af) 56 compounds of formula (II.af):







wherein R1 and R3 are as defined in Table 2.

  • ag) 56 compounds of formula (II.ag):







wherein R1 and R3 are as defined in Table 2.

  • ah) 56 compounds of formula (II.ah):







wherein R1 and R3 are as defined in Table 2.

  • ai) 56 compounds of formula (II.ai):







wherein R1 and R3 are as defined in Table 2.

  • aj) 56 compounds of formula (II.aj):







wherein R1 and R3 are as defined in Table 2.

  • ak) 56 compounds of formula (II.ak):







wherein R1 and R3 are as defined in Table 2.

  • al) 56 compounds of formula (II.al):







wherein R1 and R3 are as defined in Table 2.

  • am) 56 compounds of formula (II.am):







wherein R1 and R3 are as defined in Table 2.

  • an) 56 compounds of formula (II.an):







wherein R1 and R3 are as defined in Table 2.

  • ao) 56 compounds of formula (II.ao):







wherein R1 and R3 are as defined in Table 2.

  • ap) 56 compounds of formula (II.ap):







wherein R1 and R3 are as defined in Table 2.

  • aq) 56 compounds of formula (II.aq):







wherein R1 and R3 are as defined in Table 2.

  • ar) 56 compounds of formula (II.ar):







wherein R1 and R3 are as defined in Table 2.

  • as) 56 compounds of formula (II.as):







wherein R1 and R3 are as defined in Table 2.

  • at) 56 compounds of formula (II.at):







wherein R1 and R3 are as defined in Table 2.

  • au) 56 compounds of formula (II.au):







wherein R1 and R3 are as defined in Table 2.

  • av) 56 compounds of formula (II.av):







wherein R1 and R3 are as defined in Table 2.

  • aw) 56 compounds of formula (II.aw):







wherein R1 and R3 are as defined in Table 2.

  • ax) 56 compounds of formula (II.ax):







wherein R1 and R3 are as defined in Table 2.

  • ay) 56 compounds of formula (II.ay):







wherein R1 and R3 are as defined in Table 2.

  • az) 56 compounds of formula (II.az):







wherein R1 and R3 are as defined in Table 2.


Throughout this description, temperatures are given in degrees Celsius, m.p. means melting point and “%” is percent by weight, unless corresponding concentrations are indicated in other units.


Table 3 shows selected melting point for compounds of Tables 1 and 2.









TABLE 3







Melting point for compounds of Tables 1 and 2










Compound




Number
m.p. (° C.)







I.f.196
196-198



I.q.196
273-275



I.t.196
297-298



I.t.198
210-211



I.ac.196
224-226



I.ac.197
109-112



I.ac.199
124-127



I.ae.076
285-287



I.ae.079
182-184



I.ae.080
120-123



I.ae.196
266-268



I.ae.197
108-110



I.ae.198
86-89



I.ae.199
138-140



II.f.040
150-152



II.q.040
170-171



II.t.040
220-222



II.ae.016
170-172



II.ae.040
164-165










The compounds according to the present invention can be prepared according to the above-mentioned reaction schemes, in which, unless otherwise stated, the definition of each variable is as defined above for a compound of formula (I).


BIOLOGICAL EXAMPLES


Alternaria Solani/Tomato/Preventive (Action Against Alternaria on Tomato)


4 weeks old tomato plants cv. Roter Gnom are treated with the formulated test compound in a spray chamber. Two days after application tomato plants are inoculated by spraying a spore suspension on the test plants. After an incubation period of 4 days at 22° C./18° C. and 95% r. h. in a greenhouse the disease incidence is assessed.


Compounds of formula I according to the invention, in particular compounds I.t.198, I.ac.197, I.ae.080, I.ae.198 and I.ae.199 at 200 ppm inhibit fungal infestation in this test to at least 80%, while under the same conditions untreated control plants are infected by the phytopathogenic fungi to over 80%.



Botrytis Cinerea/Tomato/Preventive (Action Against Botrytis on Tomato)


4 weeks old tomato plants cv. Roter Gnom are treated with the formulated test compound in a spray chamber. Two days after application tomato plants are inoculated by spraying a spore suspension on the test plants. After an incubation period of 3 days at 20° C. and 95% r. h. in a greenhouse the disease incidence is assessed.


Compounds of formula I according to the invention, in particular compounds I.ac.197, I.ac.199, I.ae.079, I.ae.197, I.ae.198 and I.ae.199 at 200 ppm inhibit fungal infestation in this test to at least 80%, while under the same conditions untreated control plants are infected by the phytopathogenic fungi to over 80%.



Puccinia Recondita/Wheat/Preventive (Action Against Brown Rust on Wheat)


1 week old wheat plants cv. Arina are treated with the formulated test compound in a spray chamber. One day after application wheat plants are inoculated by spraying a spore suspension (1×105 uredospores/ml) on the test plants. After an incubation period of 1 day at 20° C. and 95% r. h. plants are kept for 10 days 20° C./18° C. (day/night) and 60% r.h. in a greenhouse. The disease incidence is assessed 11 days after inoculation.


Compounds of formula I according to the invention, in particular compounds I.ac.197, I.ae.197 and I.ae.198 at 200 ppm inhibits fungal infestation in this test to at least 80%, while under the same conditions untreated control plants are infected by the phytopathogenic fungi to over 80%.



Magnaporthe Grisea (Pyricularia Oryzae)/Rice/Preventive (Action Against Rice Blast)


3 weeks old rice plants cv. Koshihikari are treated with the formulated test compound in a spray chamber. Two days after application rice plants are inoculated by spraying a spore suspension (1×105 conidia/ml) on the test plants. After an incubation period of 6 days at 25° C. and 95% r. h. the disease incidence is assessed.


Compounds of formula I according to the invention, in particular compounds I.t.198, I.ac.199, I.ae.079, I.ae.080, I.ae.197 and I.ae.198 at 200 ppm inhibit fungal infestation in this test to at least 80%, while under the same conditions untreated control plants are infected by the phytopathogenic fungi to over 80%.



Pyrenophora Teres (Helminthosporium Teres)/Barley/Preventive (Action Against Net Blotch on Barley)


1-week-old barley plants cv. Regina are treated with the formulated test compound in a spray chamber. Two days after application barley plants are inoculated by spraying a spore suspension (2.6×104 conidia/ml) on the test plants. After an incubation period of 4 days at 20° C. and 95% r. h. the disease incidence is assessed.


Compounds of formula I according to the invention, in particular compounds I.t.198, I.ac.197, I.ae.197, I.ae.198 and I.ae.199 at 200 ppm inhibit fungal infestation in this test to at least 80%, while under the same conditions untreated control plants are infected by the phytopathogenic fungi to over 80%.



Septoria Tritici/Wheat/Preventive (Action Against Septoria Leaf Spot on Wheat)


2 weeks old wheat plants cv. Riband are treated with the formulated test compound in a spray chamber. One day after application wheat plants are inoculated by spraying a spore suspension (106 conidia/ml) on the test plants. After an incubation period of 1 day at 22° C./21° C. and 95% r. h. plants are kept at 22° C./21° C. and 70% r.h. in a greenhouse. The disease incidence is assessed 16-18 days after inoculation.


Compounds of formula I according to the invention, in particular compounds I.ac.197, I.ac.199, I.ae.080, I.ae.197 and I.ae.198 at 200 ppm inhibits fungal infestation in this test to at least 80%, while under the same conditions untreated control plants are infected by the phytopathogenic fungi to over 80%.



Uncinula Necator/Grape/Preventive (Action Against Powdery Mildew on Grape)


5 weeks old grape seedlings cv. Gutedel are treated with the formulated test compound in a spray chamber. One day after application grape plants are inoculated by shaking plants infected with grape powdery mildew above the test plants. After an incubation period of 7 days at 24° C./22° C. and 70% r. h. under a light regime of 14/10 h (light/dark) the disease incidence is assessed.


Compounds of formula I according to the invention, in particular compounds I.ac.197, I.ac.199, I.ae.079, I.ae.198 and I.ae.199 at 200 ppm inhibit fungal infestation in this test to at least 80%, while under the same conditions untreated control plants are infected by the phytopathogenic fungi to over 80%.

Claims
  • 1. A compound of formula I:
  • 2. The compound according to claim 1 wherein R1 is hydrogen, C1-C6alkyl or C1-C6haloalkyl.
  • 3. The compound according to claim 1 wherein R2 is cycloalkyl, cycloalkylalkyl, halocycloalkyl, cycloalkoxy, halocycloalkoxy, cycloalkylalkoxy, halocycloalkylalkoxy, alkoxyalkyl, cycloalkoxyalkoxyalkyl, haloalkoxyalkyl, trialkylsilyl, alkylthioalkyl, haloalkylthioalkyl, cycloalkylthio, halocycloalkylthio, cycloalkylalkylthio, halocycloalkylalkylthio, alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, haloalkylsulfonyl, C2-C6alkenyl, C2-C6alkynyl, optionally substituted arylsulfonyl, optionally substituted aryloxy, optionally substituted heteroaryloxy, optionally substituted arylthio, optionally substituted heteroarylthio; or R2 together with an adjacent carbon atom forms an optionally substituted 2- to 7-membered fused ring.
  • 4. The compound according to claim 1 wherein R3 is an optionally substituted phenyl.
  • 5. The compound according to claim 1 wherein R4 is halogen, C1-C6alkyl, C1-C6haloalkyl, C1-C6alkoxy, C1-C6haloalkoxy, 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 R1 is C1-C6alkyl or C1-C6haloalkyl;R2 is cycloalkyl, cycloalkylalkyl, halocycloalkyl, cycloalkoxy, cycloalkylalkoxy, alkoxyalkyl, cycloalkoxyalkoxyalkyl, haloalkoxyalkyl, trialkylsilyl, alkylthioalkyl, haloalkylthioalkyl, cycloalkylthio, halocycloalkylthio, cycloalkylalkylthio, halocycloalkylalkylthio, alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, haloalkylsulfonyl, C2-C6alkenyl, C2-C6alkynyl, optionally substituted arylsulfonyl, optionally substituted aryloxy, optionally substituted heteroaryloxy, optionally substituted arylthio, optionally substituted heteroarylthio; orR2 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;R3 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;R4 is halogen, C1-C6alkyl, C1-C6haloalkyl, C1-C6alkoxy, C1-C6haloalkoxy or hydroxy; andn is a whole number from 1 to 3.
  • 8. The compound according to claim 1 wherein R1 is C1-C6alkyl;R2 is cycloalkyl, cycloalkylalkyl, halocycloalkyl, cycloalkoxy, cycloalkylalkoxy, alkoxyalkyl, haloalkoxyalkyl, trialkylsilyl, alkylthioalkyl, haloalkylthioalkyl, cycloalkylthio, cycloalkylalkylthio, halocycloalkylalkylthio, alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, haloalkylsulfonyl, C2-C6alkenyl, C2-C6alkynyl, optionally substituted arylsulfonyl, optionally substituted aryloxy, optionally substituted heteroaryloxy, optionally substituted arylthio, optionally substituted heteroarylthio; orR2 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;R3 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;R4 is halogen, C1-C6alkyl, C1-C6haloalkyl, C1-C6alkoxy or hydroxy;n is a whole number from 1 to 3.
  • 9. The compound according to claim 1 wherein R1 is C1-C3alkyl;R2 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; orR2 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;R3 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;R4 is halogen, C1-C6alkyl, C1-C6alkoxy or hydroxy; andn is a whole number from 1 to 2.
  • 10. The compound according to claim 1 wherein R1 is methyl;R2 is cycloalkoxy, cycloalkylalkoxy, alkylsulfonyl, optionally substituted aryloxy; orR2 together with an adjacent carbon atom forms an optionally substituted 6-membered aromatic carbocyclic fused ring;R3 is 2-methylphenyl, 2,6-difluorophenyl, 2-chloro-6-fluorophenyl or 2,4,6-trifluorophenyl;R4 is fluoro, chloro, methyl, methoxy or hydroxy; andn 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, and3-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,
  • 13. A process for the preparation of a compound of formula I.5,
  • 14. A process for the preparation of a compound of formula II,
  • 15. A process for the preparation of a compound of formula III,
  • 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.
Priority Claims (1)
Number Date Country Kind
06022285.8 Oct 2006 EP regional
PCT Information
Filing Document Filing Date Country Kind 371c Date
PCT/EP2007/009189 10/23/2007 WO 00 12/14/2009