Title of Invention

2-SUBSTITUTED PYRIMIDINES

Abstract The invention relates to 2-substituted pyrimidines of the formula I in which the index n and the substituents R1 to R3 and L are as defined in the description and R4 corresponds to one of the formulae in which Ra, Rb and Rbare as defined in the description; and also to processes for preparing these compounds, to pesticidal compositions comprising these compounds and to their use as pesticides.
Full Text



R1,R2 independently of one another are CrC6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, where the aliphatic groups of the radical definitions of R1 and R2 for their part may be partially or fully halogenated or may carry one to four groups Rv:
Rv is cyano, C3-C6-cycloalkyl, C4-C6-cycloalkenyl, hydroxyl, d-Ce-alkoxy, C2-C8-alkenyloxy, C2-C8-alkynyloxy, C3-C6-cycloalkyloxy, C4-C6-cycloalkenyloxy, d-Ce-alkylthio, -C(=O)-A, -C(=O)-O-A, -C(=O)-N(A')A, C(A')(=N-OA), N(A')A, N(A> C(=O)-A, N(A")-C(=O)-N(A')A, S(=O)m-A, or S(=O)m-O-A or S)=O)m-N(A')A or phenyl, where the phenyl moiety may carry one to three radicals selected from the group consisting of: halogen, d-C6-alkyl, d>-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, d-C6-haloalkyl, d-C6-alkoxy, cyano, nitro, -C(=O)-A, -C(=O)-O-A, -C(=O)-N(A')A, C(A')(=N-OA), N(A')A;
R2 may additionally be hydrogen;
R1 and R2 may also, together with the nitrogen atom to which they are attached, form a saturated or unsaturated five- or six-membered ring which may be interrupted by an ether (-O-), carbonyl (C=O), thio (-S-), sulfoxyl (-S[=O]-) or sulfenyl (-SO2-) or a further amino (-N(Ra) group, where Ra is hydrogen or d-C6-alkyl, and/or may contain one or more substituents from the group consisting of halogen, d-C6-alkyl, d-Ce-haloalkyl and oxy-d-C3-alkyleneoxy;
R3 is halogen, cyano, CrC4-alkyl, C2-C4-alkenyl, C2-C4-alkynyl, C3-C6-cycloalkyl, d-C4-alkoxy, C3-C4-alkenyloxy, C3-C4-alkynyloxy, CrC6-alkylthio, di-(C1-C6-alkyl)amino or CrC6-alkylamino, where the alkyl, alkenyl and alkynyl radicals of R3 may be substituted by halogen, cyano, nitro, d-C2-alkoxy or d-d-alkoxy carbonyl;

where
X is a direct bond, -(C=O)-, -(C=O)-NH-, -(C=O)-O-, -O-, -NRC-, -CH2O-(C=O)-, -C=C-(C=O)-, where in each case the left atom of the bridge is attached to the nitrogen atom;

Ra is hydrogen, CrC6-alkyl, C2-C8-alkenyl, C2-C8-alkynyl or benzyl; Rb is hydrogen, d-C6-alkyl, C2-C6-alkenyl or C2-C6-alkynyl;
Rc is hydrogen, C1-C6-alkyl, C2-C6-alkenyI, C2-C6-alkynyl, benzyl or C1-C6-acyl, where the aliphatic, alicyclic or aromatic groups of the radical definitions of Ra, Rb and/or Rc for their part may carry one to four groups Rw:
Rw is halogen, cyano, ORX, NHR\ SRX, d-Ce-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, CrC6-alkoxy, Ci-C4-alkoxycarbonyl, d-C4-acylamino, [1,3]dioxolane-C1-C4-alkyl, [1,3]dioxane-d-C4-alkyl, where
Rx is hydrogen, d-C6-alkyl, C2-C8-alkenyl, C2-C8-alkynyl or benzyl.
Moreover, the invention relates to a process for preparing these compounds, to compositions comprising 2-pyrimidines and to their use for controlling phytopathogenic harmful fungi.
Fungicidal pyrimidines carrying a cyanamino substituent in the 2-position are known from WO-A 01/96314. Furthermore, fungicidal 2-pyrimidyl-N-methoxyamidines are known from WO-A 03/43993.
However, in many cases the activity of the abovementioned pyrimidines is unsatisfactory. It is an object of the present invention to provide compounds having improved activity.
We have found that this object is achieved by the pyrimidines of the formula I defined at the outset. Moreover, we have found processes for their preparation and compositions comprising them for controlling harmful fungi.
The compounds I can be obtained by different routes.
1) It is possible, for example, to use sulfones of the formula II whose preparation is described in detail in WO-A 02/074753 or DE 10156279.9 as starting materials. Reaction of the sulfones II with metal cyanides III (Me+CN~) yields the nitriles IV. Metal cyanides are to be understood as meaning primarily alkali metal cyanides or alkaline earth metal cyanides or else covalent cyanides, such as tin tetracyanide.








Here, the compounds of the formula IA are initially converted with the aid of strong bases into the anion and then reacted with the corresponding acid chlorides to give IA' (see J. Chem. Soc, Perkin Trans I, 1995, p. 3043). This gives compounds in which X is a C=O bridge. Bases suitable for preparing the anion are, for example, sodium amide and sodium hydride.
What was said above refers in particular to the preparation of compounds in which R3 is an alkyl group. If R3 is a cyano group or an alkoxy substituent, the radical R3 can be introduced by reaction with alkali metal cyanides and alkali metal alkoxides, respectively.
In the definitions of the symbols given in the formulae above, collective terms were used which are generally representative for the following substituents:
halogen: fluorine, chlorine, bromine and iodine;
alkyl and the alkyl moieties of, for example, alkoxy, alkylamino, alkoxycarbonyl:
saturated straight-chain or branched hydrocarbon radicals having 1 to 4, 6 or 8 carbon atoms, for example d-Ce-alkyl such as methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, hexyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyi, 1,2,2-trimethylpropyl, 1-ethyl-1-methylpropyl and 1-ethyl-2-methylpropyl;
haloalkyl: straight-chain or branched alkyl groups having 1 to 8 carbon atoms (as mentioned above), where in these groups some or all of the hydrogen atoms may be replaced by halogen atoms as mentioned above, for example CrCa-haloalkyl, such as chloromethyl, bromomethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1-chloroethyl, 1-bromoethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-



U-dimethyl-3-butynyl, 1,2-dimethyl-3-butynyl, 2,2-dimethyl-3-butynyI, 3,3-dimethyl-1-butynyl, 1-ethyl-2-butynyl, 1-ethyl-3-butynyl, 2-ethyl-3-butynyI and 1-ethyl-1-methyl-2-propynyl;
cycloalkyl: mono- or bicyclic saturated hydrocarbon groups having 3 to 6 carbon ring members, for example C3-C6-cycloalkyl such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl;
five- or six-membered saturated, partially unsaturated or aromatic heterocycle which contains one to four heteroatoms from the group consisting of O, N and S:
5- or 6-membered heterocyclyl which contains one to three nitrogen atoms and/or one oxygen or sulfur atom or one or two oxygen and/or sulfur atoms, for example 2-tetrahydrofuranyl, 3-tetrahydrofuranyl, 2-tetrahydrothienyl, 3-tetrahydrothienyl, 2-pyrrolidinyl, 3-pyrrolidinyl, 3-isoxazolidinyl, 4-isoxazolidinyl, 5-isoxazolidinyl, 3-isothiazolidinyl, 4-isothiazolidinyl, 5-isothiazolidinyl, 3-pyrazolidinyl, 4-pyrazolidinyl, 5-pyrazolidinyl, 2-oxazolidinyl, 4-oxazolidinyl, 5-oxazolidinyl, 2-thiazolidinyl, 4-thiazolidinyl, 5-thiazolidinyl, 2-imidazolidinyl, 4-imidazolidinyl, 1,2,4-oxadiazolidin-3-yl, 1,2,4-oxadiazolidin-5-yl, 1,2,4-thiadiazolidin-3-yl, 1,2,4-thiadiazolidin-5-yl, 1,2,4-triazolidin-3-yl, 1,3,4-oxadiazolidin-2-yl, 1,3,4-thiadiazolidin-2-yl, 1,3,4-triazolidin-2-yl, 2,3-dihydrofur-2-yl, 2,3-dihydrofur-3-yl, 2,4-dihydrofur-2-yl, 2,4-dihydrofur-3-yl, 2,3-dihydrothien-2-yl, 2,3-dihydrothien-3-yl, 2,4-dihydrothien-2-yl, 2,4-dihydrothien-3-yl, 2-pyrrolin-2-yl, 2-pyrrolin-3«yl, 3-pyrrolin-2-yl, 3-pyrrolin-3-yl, 2-isoxazolin-3-yl, 3-isoxazolin-3-yl, 4-isoxazolin-3-yl, 2-isoxazolin-4-yl, 3-isoxazolin-4-yl, 4-isoxazolin-4-yl, 2~ isoxazolin-5-yl, 3-isoxazolin-5-yl, 4-isoxazolin-5-yt, 2-isothiazolin-3-yl, 3-isothiazolin-3-yl, 4-isothiazolin-3-yl, 2-isothiazolin-4-yl, 3-isothiazolin-4-yl, 4-isothiazolin-4-yl, 2-isothiazolin-5-yl, 3-isothiazolin-5-yl, 4-isothiazolin-5-yl, 2,3-dihydropyrazol-1-yl, 2,3-dihydropyrazol-2-yl, 2,3-dihydropyrazol-3-yl, 2,3-dihydropyrazol-4-yl, 2,3-dihydropyrazol-5-yl, 3,4-dihydropyrazol-1-yl, 3,4-dihydropyrazol-3-yl, 3,4-dihydropyrazol-4-yl, 3,4-dihydropyrazol-5-yl, 4,5-dihydropyrazol-1-yl, 4,5-dihydropyrazol-3-yl, 4,5-dihydropyrazol-4-yl, 4,5-dihydropyrazol-5-yl, 2,3-dihydrooxazol-2-yl, 2,3-dihydrooxazol-3-yl, 2,3-dihydrooxazol-4-yl, 2,3-dihydrooxazol-5-yl, 3,4-dihydrooxazol-2-yl, 3,4-dihydrooxazol-3-yl, 3,4-dihydrooxazol-4-yl, 3,4-dihydrooxazol-5-yl, 3,4-dihydrooxazol-2-yl, 3,4-dihydrooxazol-3-yl, 3,4-dihydrooxazol-4-yl, 2-piperidinyl, 3-piperidinyl, 4-piperidinyl, 1,3-dioxan-5-yl, 2-tetrahydropyranyl, 4-tetrahydropyranyl, 2-tetrahydrothienyl, 3-hexahydropyridazinyl, 4-hexahydropyridazinyl, 2-hexahydropyrimidinyl, 4-hexahydropyrimidinyl, 5-



In addition, preference is given to compounds I in which R1 is C1-C4-haloalkyl and R2 is hydrogen.
Moreover, preference is given to compounds I in which R1 and R2 together with the nitrogen to which they are attached form a five- or six-membered ring which may be interrupted by an oxygen atom and may carry one or two C1-C6-alkyl substituents.
Especially preferred are groups NR1R2 such as - in particular in the a-position -methylated pyrrolidines or piperidines. Preference is furthermore given to 4-methylpiperidine.
Especially preferred are pyrimidines I in which the substituents L1 to L5 are as defined below:
L is halogen, cyano, CrC8-alkyl, CrC6-alkoxy, -C(=O)-O-A, -C(=O)-N(A')A,
A, A1, A" independently of one another are hydrogen, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl.
Moreover, preference is given to pyrimidines I where the phenyl group substituted by Ln is the group B
where # is the point of attachment to the pyrimidine skeleton and
L1 is fluorine, chlorine, CH3 or CF3;
L2,L4 independently of one another are hydrogen, CH3 or fluorine;
L3 is hydrogen, fluorine, chlorine, bromine, cyano, CH3, SCH3, OCH3, SO2CH3,
CO-NH2, CO-NHCH3, CO-NHC2H5, CO-N(CH3)2, NH-C(=O)CH3, N(CH3)-
C(=O)CH3 or COOCH3 and L5 is hydrogen, fluorine, chlorine or CH3.
Particular preference is also given to compounds I in which R3 is C1-C4-alkyl which may be substituted by halogen.
Moreover, particular preference is given to compounds I in which R3 is halogen, cyano, C1-C4-alkyl or C1-C4-alkoxy.







Table 1
Compounds of the formulae la, Ib, Ic, Id, le, If, Ig, Ih, li and Va in which Ln is 2-fluoro-6-chloro, R3 is methyl and R1, R2 for a compound correspond in each case to one row of Table A
Table 2
Compounds of the formulae la, Ib, Ic, Id, le, If, Ig, Ih, li and Va in which Ln is 2,6-difluoro, R3 is methyl and R\ R2 for a compound correspond in each case to one row of Table A
Table 3
Compounds of the formulae la, Ib, Ic, Id, le, If, Ig, Ih, li and Va in which Ln is 2,6-dichloro, R3 is methyl and R1, R2 for a compound correspond in each case to one row of Table A
Table 4
Compounds of the formulae la, Ib, Ic, Id, le, If, Ig, Ih, li and Va in which Ln is 2-fluoro-6-methyl, R3 is methyl and R1, R2 for a compound correspond in each case to one row of Table A
Table 5
Compounds of the formulae la, Ib, Ic, Id, le, If, Ig, Ih, li and Va in which Ln is 2,4,6-trifluoro, R3 is methyl and R1, R2 for a compound correspond in each case to one row of Table A
Table 6
Compounds of the formulae la, Ib, Ic, Id, le, If, Ig, Ih, li and Va in which Ln is 2-methyl-4-fluoro, R3 is methyl and R\ R2 for a compound correspond in each case to one row of Table A
Table 7
Compounds of the formulae la, Ib, Ic, Id, le, If, Ig, Ih, li and Va in which Ln is 2-fluoro-4-methoxycarbonyl, R3 is methyl and R1, R2 for a compound correspond in each case to one row of Table A
Table 8
Compounds of the formulae la, Ib, Ic, Id, le, If, Ig, Ih, li and Va in which Ln is 2-fluoro-4-CN, R3 is methyl and R1, R2 for a compound correspond in each case to one row of Table A

Table 9
Compounds of the formulae la, Ib, Ic, Id, le, If, Ig, Ih, li and Va in which Ln is 2,4,5-trifluoro, R3 is methyl and R1, R2 for a compound correspond in each case to one row of Table A
Table 10
Compounds of the formulae la, Ib, Ic, Id, le, If, Ig, Ih, li and Va in which Ln is 2,4-dichloro, R3 is methyl and R1, R2 for a compound correspond in each case to one row of Table A
Table 11
Compounds of the formulae la, Ib, Ic, Id, le, If, Ig, Ih, li and Va in which Ln is 2-chloro,
R3 is methyl and R1, R2 for a compound correspond in each case to one row of Table A
Table 12
Compounds of the formulae la, Ib, Ic, Id, le, If, Ig, Ih, li and Va in which Ln is 2-fluoro,
R3 is methyl and R1, R2 for a compound correspond in each case to one row of Table A
Table 13
Compounds of the formulae la, Ib, Ic, Id, le, If, Ig, Ih, li and Va in which Ln is
2,4-difluoro, R3 is methyl and R1, R2 for a compound correspond in each case to one
row of Table A
Table 14
Compounds of the formulae la, Ib, Ic, Id, le, If, Ig, Ih, li and Va in which Ln is 2-fluoro-4-chloro, R3 is methyl and R1, R2 for a compound correspond in each case to one row of Table A
Table 15
Compounds of the formulae la, Ib, Ic, Id, le, If, Ig, Ih, li and Va in which Ln is 2-chloro-4-fluoro, R3 is methyl and R1, R2 for a compound correspond in each case to one row of Table A
Table 16
Compounds of the formulae la, Ib, Ic, Id, le, If, Ig, Ih, li and Va in which Ln is 2,3-difluoro, R3 is methyl and R\ R2 for a compound correspond in each case to one row of Table A
Table 17

Compounds of the formulae la, Ib, Ic, Id, le, If, Ig, Ih, li and Va in which Ln is 2,5-difluoro, R3 is methyl and R1, R2 for a compound correspond in each case to one row of Table A
Table 18
Compounds of the formulae la, Ib, Ic, Id, le, If, Ig, Ih, li and Va in which Ln is 2,3,4-trifluoro, R3 is methyl and R1, R2 for a compound correspond in each case to one row of Table A
Table 19
Compounds of the formulae la, Ib, Ic, Id, le, If, Ig, Ih, li and Va in which Ln is 2-methyl,
R3 is methyl and R1, R2 for a compound correspond in each case to one row of Table A
Table 20
Compounds of the formulae la, Ib, Ic, Id, le, If, Ig, Ih, li and Va in which Ln is 2,4-dimethyl, R3 is methyl and R\ R2 for a compound correspond in each case to one row of Table A
Table 21
Compounds of the formulae la, Ib, Ic, Id, le, If, Ig, Ih, li and Va in which Ln is 2-methyl-4-chloro, R3 is methyl and R1, R2 for a compound correspond in each case to one row of Table A
Table 22
Compounds of the formulae la, Ib, Ic, Id, le, If, Ig, Ih, li and Va in which Lnis 2-fluoro-4-methyl, R3 is methyl and R1, R2 for a compound correspond in each case to one row of Table A
Table 23
Compounds of the formulae la, Ib, Ic, Id, le, If, Ig, Ih, li and Va in which Lnis 2,6-dimethyl, R3 is methyl and R1, R2 for a compound correspond in each case to one row of Table A
Table 24
Compounds of the formulae la, Ib, Ic, Id, le, If, Ig, Ih, li and Va in which Lnis 2,4,6-trimethyl, R3 is methyl and R1, R2 for a compound correspond in each case to one row of Table A
Table 25

Compounds of the formulae la, Ib, Ic, Id, le, If, Ig, Ih, li and Va in which Lnis 2,6-difluoro-4-cyano, R3 is methyl and R1, R2 for a compound correspond in each case to one row of Table A
Table 26
Compounds of the formulae la, Ib, Ic, Id, le, If, Ig, Ih, li and Va in which Ln is 2,6-difluoro-4-methyl, R3 is methyl and R1, R2 for a compound correspond in each case to one row of Table A
Table 27
Compounds of the formulae la, Ib, Ic, Id, le, If, Ig, Ih, li and Va in which Lnis 2,6-difluoro-4-methoxycarbonyl, R3 is methyl and R1, R2 for a compound correspond in each case to one row of Table A
Table 28
Compounds of the formulae la, Ib, Ic, Id, le, If, Ig, Ih, li and Va in which Lnis 2-chloro, 4-methoxy, R3 is methyl and R1, R2 for a compound correspond in each case to one row of Table A
Table 29
Compounds of the formulae la, Ib, Ic, Id, le, If, Ig, Ih, li and Va in which Ln is 2-chloro, 4-methyl, R3 is methyl and R1, R2 for a compound correspond in each case to one row of Table A
Table 30
Compounds of the formulae la, Ib, Ic, Id, le, If, ig, Ih, li and Va in which Ln is 2-chloro, 4-methoxycarbonyl, R3 is methyl and R1, R2 for a compound correspond in each case to one row of Table A
Table 31
Compounds of the formulae la, Ib, Ic, Id, le, If, Ig, Ih, li and Va in which Ln is 2-chloro, 4-bromo, R3 is methyl and R1, R2 for a compound correspond in each case to one row of Table A
Table 32
Compounds of the formulae la, Ib, Ic, Id, le, If, Ig, Ih, li and Va in which Lnis 2-chloro, 4-cyano, R3 is methyl and R1, R2 for a compound correspond in each case to one row of Table A
Table 33

Compounds of the formulae la, Ib, Ic, Id, le, If, Ig, Ih, li and Va in which Lnis 2,6-difluoro, 4-methoxy, R3 is methyl and R1, R2 for a compound correspond in each case to one row of Table A
Table 34
Compounds of the formulae la, Ib, Ic, Id, le, If, Ig, Ih, li and Va in which Ln is 2-fluoro, 3-methyl, R3 is methyl and R\ R2 for a compound correspond in each case to one row of Table A
Table 35
Compounds of the formulae la, Ib, Ic, Id, le, If, Ig, Ih, li and Va in which Lnis 2,5-dimethyl, R3 is methyl and R1, R2 for a compound correspond in each case to one row of Table A
Table 36
Compounds of the formulae la, Ib, Ic, Id, le, If, Ig, Ih, li and Va in which Ln is 2-methyl, 4-cyano, R3 is methyl and R1, R2 for a compound correspond in each case to one row of Table A
Table 37
Compounds of the formulae la, Ib, Ic, Id, le, If, Ig, Ih, li and Va in which Lnis 2-methyl, 4-bromo, R3 is methyl and R1, R2 for a compound correspond in each case to one row of Table A
Table 38
Compounds of the formulae la, Ib, Ic, Id, le, If, Ig, Ih, li and Va in which Lnis 2-methyl, 5-fluoro, R3 is methyl and R1, R2 for a compound correspond in each case to one row of Table A
Table 39
Compounds of the formulae la, Ib, Ic, Id, le, If, Ig, Ih, li and Va in which Lnis 2-methyl, 4-methoxy, R3 is methyl and R1, R2 for a compound correspond in each case to one row of Table A
Table 40
Compounds of the formulae la, Ib, Ic, Id, le, If, Ig, Ih, li and Va in which Ln is 2-methyl, 4-methoxycarbonyl, R3 is methyl and R1, R2for a compound correspond in each case to one row of Table A
Table 41

Compounds of the formulae la, Ib, Ic, Id, le, If, Ig, Ih, li and Va in which Ln is 2,5-dimethyl, 4-bromo, R3 is methyl and R1, R2 for a compound correspond in each case to one row of Table A
Table 42
Compounds of the formulae la, Ib, Ic, Id, le, If, Ig, Ih, li and Va in which Lnis 2-fluoro, 4-bromo, R3 is methyl and R1, R2 for a compound correspond in each case to one row of Table A
Table 43
Compounds of the formulae la, Ib, Ic, Id, le, If, Ig, Ih, li and Va in which Lnis 2-fluoro, 4-methoxy, R3 is methyl and R1, R2 for a compound correspond in each case to one row of Table A
Table 44
Compounds of the formulae la, Ib, Ic, Id, le, If, Ig, Ih, li and Va in which Lnis 2-fluoro, 5-methyl, R3 is methyl and R1, R2 for a compound correspond in each case to one row of Table A
Table 45
Compounds of the formulae la, Ib, Ic, Id, le, If, Ig, Ih, li and Va in which Lnis pentafluoro, R3 is methyl and R1, R2 for a compound correspond in each case to one row of Table A
Table 46
Compounds of the formulae la, Ib, Ic, Id, le, If, Ig, Ih, li and Va in which Ln is 2-fluoro, 6-chloro, R3 is chloro and R1, R2 for a compound correspond in each case to one row of Table A
Table 47
Compounds of the formulae la, Ib, Ic, Id, le, If, Ig, Ih, li and Va in which Ln is 2,6-difluoro, R3 is chloro and R1, R2 for a compound correspond in each case to one row of Table A
Table 48
Compounds of the formulae laf Ib, Ic, Id, le, If, Ig, Ih, li and Va in which Ln is 2,6-dichloro, R3 is chloro and R1, R2 for a compound correspond in each case to one row of Table A
Table 49

Compounds of the formulae la, Ib, Ic, Id, le, If, Ig, Ih, li and Va in which Ln is 2-fluoro, 6-methyl, R3 is chloro and R1, R2 for a compound correspond in each case to one row of Table A
Table 50
Compounds of the formulae la, Ib, Ic, Id, le, If, Ig, Ih, li and Va in which Ln is 2,4,6-trifluoro, R3 is chloro and R1, R2 for a compound correspond in each case to one row of Table A
Table 51
Compounds of the formulae la, Ib, Ic, Id, le, If, Ig, Ih, li and Va in which Ln is 2-methyl, 4-fluoro, R3 is chloro and R1, R2 for a compound correspond in each case to one row of Table A
Table 52
Compounds of the formulae la, Ib, Ic, Id, le, If, Ig, Ih, li and Va in which Ln is 2-fluoro, 4-methoxycarbonyl, R3 is chloro and R1, R2 fora compound correspond in each case to one row of Table A
Table 53
Compounds of the formulae la, Ib, Ic, Id, le, If, Ig, Ih, li and Va in which Ln is 2-fluoro, 4-CN, R3 is chloro and R\ R2 for a compound correspond in each case to one row of Table A
Table 54
Compounds of the formulae la, Ib, Ic, Id, le, If, Ig, Ih, li and Va in which Ln is 2,4,5-trifluoro, R3 is chloro and R1, R2 for a compound correspond in each case to one row of Table A
Table 55
Compounds of the formulae la, Ib, Ic, Id, le, If, Ig, Ih, li and Va in which Ln is 2,4-dichloro, R3 is chloro and R1, R2 for a compound correspond in each case to one row of Table A
Table 56
Compounds of the formulae la, Ib, Ic, Id, le, If, Ig, Ih, li and Va in which Ln is 2-chloro,
R3 is chloro and R1, R2 for a compound correspond in each case to one row of Table A
Table 57

Compounds of the formulae la, Ib, Ic, Id, le, If, Ig, Ih, li and Va in which Ln is 2-fluoro, R3 is chloro and R1, R2 for a compound correspond in each case to one row of Table A
Table 58
Compounds of the formulae la, Ib, Ic, Id, le, If, Ig, Ih, li and Va in which Ln is 2,4-difluoro, R3 is chloro and R1, R2 for a compound correspond in each case to one row of Table A
Table 59
Compounds of the formulae la, Ib, Ic, Id, le, If, Ig, Ih, li and Va in which Ln is 2-fluoro-4-chloro, R3 is chloro and R1, R2 for a compound correspond in each case to one row of Table A
Table 60
Compounds of the formulae la, Ib, Ic, Id, le, If, Ig, Ih, li and Va in which Ln is 2-chIoro-4-fluoro, R3 is chloro and R1, R2 for a compound correspond in each case to one row of Table A
Table 61
Compounds of the formulae la, Ib, Ic, Id, le, If, Ig, Ih, li and Va in which Ln is 2,3-difluoro, R3 is chloro and R1, R2 for a compound correspond in each case to one row of Table A
Table 62
Compounds of the formulae la, Ib, Ic, Id, le, If, Ig, Ih, li and Va in which Ln is 2,5-difluoro, R3 is chloro and R1, R2 for a compound correspond in each case to one row of Table A
Table 63
Compounds of the formulae la, Ib, Ic, Id, le, If, Ig, Ih, li and Va in which Ln is 2,3,4-trifluoro, R3 is chloro and R1, R2 for a compound correspond in each case to one row of Table A
Table 64
Compounds of the formulae la, Ib, Ic, Id, le, If, Ig, Ih, li and Va in which Ln is 2-methyl,
R3 is chloro and R1, R2 for a compound correspond in each case to one row of Table A
Table 65

Compounds of the formulae la, Ib, Ic, Id, le, If, Ig, Ih, li and Va in which l_n is 2,4-dimethyl, R3 is chloro and R1, R2 for a compound correspond in each case to one row of Table A
Table 66
Compounds of the formulae la, Ib, Ic, Id, le, If, Ig, Ih, li and Va in which Ln is 2-methyl-4-chloro, R3 is chloro and R1, R2 for a compound correspond in each case to one row of Table A
Table 67
Compounds of the formulae la, Ib, Ic, Id, le, If, Ig, Ih, li and Va in which Lnis 2-fluoro-4-methyl, R3 is chloro and R1, R2 for a compound correspond in each case to one row of Table A
Table 68
Compounds of the formulae la, Ib, Ic, Id, le, If, Ig, Ih, li and Va in which Lnis 2,6-dimethyl, R3 is chloro and R1, R2 for a compound correspond in each case to one row of Table A
Table 69
Compounds of the formulae la, Ib, Ic, Id, le, If, Ig, Ih, li and Va in which Ln is 2,4,6-trimethyl, R3 is chloro and R1, R2 for a compound correspond in each case to one row of Table A
Table 70
Compounds of the formulae la, Ib, Ic, Id, le, If, Ig, Ih, li and Va in which Ln is 2,6-difluoro-4-cyano, R3 is chloro and R1, R2 for a compound correspond in each case to one row of Table A
Table 71
Compounds of the formulae la, Ib, Ic, Id, le, If, Ig, Ih, li and Va in which Ln is 2,6-difluoro-4-methyl, R3 is chloro and R1, R2 for a compound correspond in each case to one row of Table A
Table 72
Compounds of the formulae la, Ib, Ic, Id, le, If, Ig, Ih, li and Va in which Ln is 2,6-difluoro-4-methoxycarbonyl1 R3 is chloro and R1, R2 for a compound correspond in each case to one row of Table A
Table 73

Compounds of the formulae la, Ib, Ic, Id, le, If, Ig, Ih, li and Va in which Lnis 2-chloro, 4-methoxy, R3 is chloro and R1, R2 for a compound correspond in each case to one row of Table A
Table 74
Compounds of the formulae la, Ib, Ic, Id, le, If, Ig, Ih, li and Va in which Lnis 2-chloro, 4-methyl, R3 is chloro and R1, R2 for a compound correspond in each case to one row of Table A
Table 75
Compounds of the formulae la, Ib, Ic, Id, le, If, Ig, Ih, li and Va in which Ln is 2-chloro, 4-methoxycarbonyl, R3 is chloro and R1, R2 for a compound correspond in each case to one row of Table A
Table 76
Compounds of the formulae la, Ib, Ic, Id, le, If, Ig, Ih, li and Va in which Lnis 2-chloro, 4-bromo, R3 is chloro and R\ R2 for a compound correspond in each case to one row of Table A
Table 77
Compounds of the formulae la, Ib, Ic, Id, le, If, Ig, Ih, li and Va in which Ln is 2-chloro, 4-cyano, R3 is chloro and R1, R2 for a compound correspond in each case to one row of Table A
Table 78
Compounds of the formulae la, Ib, Ic, Id, le, If, Ig, Ih, li and Va in which Lnis 2,6-difluoro, 4-methoxy, R3 is chloro and R1, R2 for a compound correspond in each case to one row of Table A
Table 79
Compounds of the formulae la, Ib, Ic, Id, le, If, Ig, Ih, li and Va in which Ln is 2-fluoro, 3-methyl, R3 is chloro and R1, R2 for a compound correspond in each case to one row of Table A
Table 80
Compounds of the formulae la, Ib, Ic, Id, le, If, Ig, Ih, li and Va in which Ln is 2,5-dimethyl, R3 is chloro and R1, R2 for a compound correspond in each case to one row of Table A
Table 81

Compounds of the formulae la, Ib, Ic, Id, le, If, Ig, Ih, li and Va in which Ln is 2-methyl, 4-cyano, R3 is chloro and R1, R2 for a compound correspond in each case to one row of Table A
Table 82
Compounds of the formulae la, Ib, Ic, Id, le, If, Ig, Ih, li and Va in which Ln is 2-methyl, 4-bromo, R3 is chloro and R1, R2 for a compound correspond in each case to one row of Table A
Table 83
Compounds of the formulae la, Ib, Ic, Id, le, If, Ig, Ih, li and Va in which Ln is 2-methyl, 5-fluoro, R3 is chloro and R1, R2 for a compound correspond in each case to one row of Table A
Table 84
Compounds of the formulae la, Ib, Ic, Id, le, If, Ig, Ih, li and Va in which Ln is 2-methyi, 4-methoxy, R3 is chloro and R1, R2 for a compound correspond in each case to one row of Table A
Table 85
Compounds of the formulae la, Ib, Ic, Id, le, If, Ig, Ih, li and Va in which Ln is 2-methyl, 4-methoxycarbonyl, R3 is chloro and R1, R2 for a compound correspond in each case to one row of Table A
Table 86
Compounds of the formulae la, Ib, Ic, Id, le, If, Ig, Ih, li and Va in which Ln is 2,5-dimethyl, 4-bromo, R3 is chloro and R1, R2 for a compound correspond in each case to one row of Table A
Table 87
Compounds of the formulae la, Ib, Ic, Id, le, If, Ig, Ih, li and Va in which Ln is 2-fluoro, 4-bromo, R3 is chloro and R1, R2 for a compound correspond in each case to one row of Table A
Table 88
Compounds of the formulae la, Ib, Ic, Id, le, If, Ig, Ih, li and Va in which Ln is 2-fluoro, 4-methoxy, R3 is chloro and R1, R2 for a compound correspond in each case to one row of Table A
Table 89

Compounds of the formulae la, Ib, Ic, Id, le, If, Ig, Ih, li and Va in which Ln is 2-fluoro, 5-methyl, R3 is chloro and R\ R2 for a compound correspond in each case to one row of Table A
Table 90
Compounds of the formulae la, Ib, Ic, Id, le, If, Ig, Ih, li and Va in which Ln is pentafluoro, R3 is chloro and R\ R2 for a compound correspond in each case to one row of Table A
Table 91
Compounds of the formulae la, Ib, Ic, Id, le, If, Ig, Ih, li and Va in which Ln is 2-fluoro, 6-chloro, R3 is methoxy and R1, R2 for a compound correspond in each case to one row of Table A
Table 92
Compounds of the formulae la, Ib, Ic, Id, le, If, Ig, Ih, li and Va in which Ln is 2,6-difluoro, R3 is methoxy and R1, R2 for a compound correspond in each case to one row of Table A
Table 93
Compounds of the formulae la, Ib, Ic, Id, le, If, Ig, Ih, li and Va in which Ln is 2,6-dichloro, R3 is methoxy and R1, R2 for a compound correspond in each case to one row of Table A
Table 94
Compounds of the formulae la, Ib, Ic, Id, le, If, Ig, Ih, li and Va in which Ln is 2-fluoro, 6-methyl, R3 is methoxy and R1, R2 for a compound correspond in each case to one row of Table A
Table 95
Compounds of the formulae la, Ib, Ic, Id, le, If, Ig, Ih, li and Va in which Ln is 2,4,6-trifluoro, R3 is methoxy and R1, R2 for a compound correspond in each case to one row of Table A
Table 96
Compounds of the formulae la, Ib, Ic, Id, le, If, Ig, Ih, li and Va in which Ln is 2-methyl, 4-fluoro, R3 is methoxy and R1, R2 for a compound correspond in each case to one row of Table A
Table 97

Compounds of the formulae la, Ib, Ic, Id, le, If, Ig, Ih, li and Va in which Ln is 2-fluoro, 4-methoxycarbonyl, R3 is methoxy and R\ R2 for a compound correspond in each case to one row of Table A
Table 98
Compounds of the formulae la, Ib, Ic, Id, le, If, Ig, Ih, li and Va in which Ln is 2-fluoro, 4-CN, R3 is methoxy and R1, R2 for a compound correspond in each case to one row of Table A
Table 99
Compounds of the formulae la, Ib, Ic, Id, le, If, Ig, Ih, li and Va in which Ln is 2,4,5-trifluoro, R3 is methoxy and R\ R2 for a compound correspond in each case to one row of Table A
Table 100
Compounds of the formulae la, Ib, Ic, Id, le, If, Ig, Ih, li and Va in which Ln is 2,4-dichloro, R3 is methoxy and R1, R2 for a compound correspond in each case to one row of Table A
Table 101
Compounds of the formulae la, Ib, Ic, Id, le, If, Ig, Ih, li and Va in which Lnis 2-chloro, R3 is methoxy and R1, R2 for a compound correspond in each case to one row of Table A
Table 102
Compounds of the formulae la, Ib, Ic, Id, le, If, Ig, Ih, li and Va in which Ln is 2-fluoro, R3 is methoxy and R1, R2 for a compound correspond in each case to one row of Table A
Table 103
Compounds of the formulae la, Ib, Ic, Id, le, If, Ig, Ih, li and Va in which Lnis 2,4-difluoro, R3 is methoxy and R1, R2 for a compound correspond in each case to one row of Table A
Table 104
Compounds of the formulae la, Ib, Ic, Id, le, If, Ig, Ih, li and Va in which Ln is 2-fluoro-4-chIoro, R3 is methoxy and R1, R2 for a compound correspond in each case to one row of Table A
Table 105

Compounds of the formulae la, Ib, Ic, Id, le, If, Ig, Ih, li and Va in which Ln is 2-chloro-4-fluoro, R3 is methoxy and R1, R2 for a compound correspond in each case to one row of Table A
Table 106
Compounds of the formulae la, Ib, Ic, Id, le, If, Ig, Ih, li and Va in which Ln is 2,3-difluoro, R3 is methoxy and R1, R2 for a compound correspond in each case to one row of Table A
Table 107
Compounds of the formulae la, Ib, Ic, Id, le, If, Ig, Ih, li and Va in which Lnis 2,5-difluoro, R3 is methoxy and R1, R2 for a compound correspond in each case to one row of Table A
Table 108
Compounds of the formulae la, Ib, Ic, Id, le, If, Ig, Ih, li and Va in which Ln is 2,3,4-trifluoro, R3 is methoxy and R1, R2 for a compound correspond in each case to one row of Table A
Table 109
Compounds of the formulae la, Ib, Ic, Id, le, If, Ig, Ih, li and Va in which Lnis 2-methyl, R3 is methoxy and R1, R2 for a compound correspond in each case to one row of Table A
Table 110
Compounds of the formulae la, Ib, Ic, Id, le, If, Ig, Ih, li and Va in which Lnis 2,4-dimethyl, R3 is methoxy and R\ R2 for a compound correspond in each case to one row of Table A
Table 111
Compounds of the formulae la, Ib, Ic, Id, le, If, Ig, Ih, li and Va in which Ln is 2-methyl-4-chloro, R3 is methoxy and R1, R2 for a compound correspond in each case to one row of Table A
Table 112
Compounds of the formulae la, Ib, Ic, Id, le, If, Ig, Ih, li and Va in which Ln is 2-fluoro-4-methyl, R3 is methoxy and R1, R2 for a compound correspond in each case to one row of Table A
Table 113

Compounds of the formulae la, Ib, Ic, Id, le, If, Ig, Ih, li and Va in which Ln is 2,6-dimethyl, R3 is methoxy and R1, R2 for a compound correspond in each case to one row of Table A
Table 114
Compounds of the formulae la, Ib, Ic, Id, le, If, Ig, Ih, li and Va in which Ln is 2,4,6-trimethyl, R3 is methoxy and R1, R2 for a compound correspond in each case to one row of Table A
Table 115
Compounds of the formulae la, Ib, Ic, Id, le, If, Ig, Ih, li and Va in which Ln is 2,6-difluoro-4-cyano, R3 is methoxy and R1, R2 for a compound correspond in each case to one row of Table A
Table 116
Compounds of the formulae la, Ib, Ic, Id, le, If, Ig, Ih, li and Va in which Ln is 2,6-difluoro-4-methyl, R3 is methoxy and R1, R2 for a compound correspond in each case to one row of Table A
Table 117
Compounds of the formulae la, Ib, Ic, Id, le, If, Ig, Ih, li and Va in which Ln is 2,6-difluoro-4-methoxycarbonyl, R3 is methoxy and R1, R2for a compound correspond in each case to one row of Table A
Table 118
Compounds of the formulae la, Ib, Ic, Id, le, If, Ig, Ih, li and Va in which Ln is 2-chloro, 4-methoxy, R3 is methoxy and R1, R2 for a compound correspond in each case to one row of Table A
Table 119
Compounds of the formulae la, Ib, Ic, Id, le, If, Ig, Ih, li and Va in which Ln is 2-chloro, 4-methyl, R3 is methoxy and R1, R2 for a compound correspond in each case to one row of Table A
Table 120
Compounds of the formulae la, Ib, Ic, Id, le, If, Ig, Ih, li and Va in which Ln is 2-chloro, 4-methoxycarbonyl, R3 is methoxy and R1, R2 for a compound correspond in each case to one row of Table A
Table 121

Compounds of the formulae la, Ib, Ic, Id, le, If, Ig, Ih, li and Va in which Ln is 2-chloro, 4-methoxy, R3 is methoxy and R1, R2 for a compound correspond in each case to one row of Table A
Table 122
Compounds of the formulae la, Ib, Ic, Id, le, If, Ig, Ih, li and Va in which Ln is 2-chloro, 4-cyano, R3 is methoxy and R1, R2 for a compound correspond in each case to one row of Table A
Table 123
Compounds of the formulae la, Ib, Ic, Id, le, If, Ig, Ih, li and Va in which Ln is 2,6-difluoro, 4-methoxy, R3 is methoxy and R1, R2 for a compound correspond in each case to one row of Table A
Table 124
Compounds of the formulae la, Ib, Ic, Id, le, If, Ig, Ih, li and Va in which Lnis 2-fluoro, 3-methyl, R3 is methoxy and R1, R2 for a compound correspond in each case to one row of Table A
Table 125
Compounds of the formulae la, Ib, Ic, Id, le, If, Ig, Ih, li and Va in which Lnis 2,5-dimethyl, R3 is methoxy and R1, R2 for a compound correspond in each case to one row of Table A
Table 126
Compounds of the formulae la, Ib, Ic, Id, le, If, Ig, Ih, li and Va in which Ln is 2-methyl, 4-cyano, R3 is methoxy and R1, R2 for a compound correspond in each case to one row of Table A
Table 127
Compounds of the formulae la, Ib, Ic, Id, le, If, Ig, Ih, li and Va in which Lnis 2-methyl, 4-bromo, R3 is methoxy and R1, R2 for a compound correspond in each case to one row of Table A
Table 128
Compounds of the formulae la, Ib, Ic, Id, le, If, Ig, Ih, li and Va in which Lnis 2-methyl, 5-fluoro, R3 is methoxy and R1, R2 for a compound correspond in each case to one row of Table A
Table 129

Compounds of the formulae la, Ib, Ic, Id, le, If, Ig, Ih, li and Va in which Ln is 2-methyl, 4-methoxy, R3 is methoxy and R1, R2 for a compound correspond in each case to one row of Table A
Table 130
Compounds of the formulae la, Ib, Ic, Id, le, If, Ig, Ih, li and Va in which Ln is 2-methyl, 4-methoxycarbonyl, R3 is methoxy and R1, R2 for a compound correspond in each case to one row of Table A
Table 131
Compounds of the formulae la, Ib, Ic, Id, le, If, Ig, Ih, li and Va in which Ln is 2,5-dimethyl, 4-bromo, R3 is methoxy and R1, R2 for a compound correspond in each case to one row of Table A
Table 132
Compounds of the formulae la, Ib, Ic, Id, le, If, Ig, Ih, li and Va in which Lnis 2-fluoro, 4-bromo, R3 is methoxy and R1, R2 for a compound correspond in each case to one row of Table A
Table 133
Compounds of the formulae la, Ib, Ic, Id, le, If, Ig, Ih, li and Va in which Lnis 2-fluoro, 4-methoxy, R3 is methoxy and R1, R2 for a compound correspond in each case to one row of Table A
Table 134
Compounds of the formulae la, Ib, Ic, Id, le, If, Ig, Ih, li and Va in which Ln is 2-fluoro, 5-methyl, R3 is methoxy and R\ R2 for a compound correspond in each case to one row of Table A
Table 135
Compounds of the formulae la, Ib, Ic, Id, le, If, Ig, Ih, li and Va in which Ln is pentafluoro, R3 is methoxy and R1, R2 for a compound correspond in each case to one row of Table A
Table 136
Compounds of the formulae la, Ib, Ic, Id, le, If, Ig, Ih, li and Va in which Ln is 2-fluoro, 6-chloro, R3 is cyano and R1, R2 for a compound correspond in each case to one row of Table A
Table 137

Compounds of the formulae la, Ib, Ic, Id, le, If, Ig, Ih, li and Va in which Ln is 2,6-difluoro, R3 is cyano and R\ R2 for a compound correspond in each case to one row of Table A
Table 138
Compounds of the formulae la, Ib, Ic, Id, le, If, Ig, Ih, li and Va in which Ln is 2,6-dichloro, R3 is cyano and R1, R2 for a compound correspond in each case to one row of Table A
Table 139
Compounds of the formulae la, Ib, Ic, Id, le, If, Ig, Ih, li and Va in which Ln is 2-fluoro, 6-methyl, R3 is cyano and R1, R2 for a compound correspond in each case to one row of Table A
Table 140
Compounds of the formulae la, Ib, Ic, Id, le, If, Ig, Ih, li and Va in which Ln is 2,4,6-trifluoro, R3 is cyano and R1, R2 for a compound correspond in each case to one row of Table A
Table 141
Compounds of the formulae la, Ib, Ic, Id, le, If, Ig, Ih, li and Va in which Ln is 2-methyl, 4-fluoro, R3 is cyano and R\ R2 for a compound correspond in each case to one row of Table A
Table 142
Compounds of the formulae la, Ib, Ic, Id, le, If, Ig, Ih, li and Va in which Ln is 2-fluoro, 4-methoxycarbonyl, R3 is cyano and R\ R2 for a compound correspond in each case to one row of Table A
Table 143
Compounds of the formulae la, Ib, Ic, Id, le, If, Ig, Ih, li and Va in which Ln is 2-fluoro, 4-CN, R3 is cyano and R1, R2 for a compound correspond in each case to one row of Table A
Table 144
Compounds of the formulae la, Ib, Ic, Id, le, If, Ig, Ih, li and Va in which Ln is 2,4,5-trifluoro, R3 is cyano and R1, R2 for a compound correspond in each case to one row of Table A
Table 145

Compounds of the formulae la, Ib, Ic, Id, le, If, Ig, Ih, li and Va in which Ln is 2,4-dichloro, R3 is cyano and R1, R2 for a compound correspond in each case to one row of Table A
Table 146
Compounds of the formulae la, Ib, Ic, Id, le, If, Ig, Ih, li and Va in which Ln is 2-chloro,
R3 is cyano and R1, R2 for a compound correspond in each case to one row of Table A
Table 147
Compounds of the formulae la, Ib, Ic, Id, le, If, Ig, Ih, li and Va in which Ln is 2-fluoro,
R3 is cyano and R1, R2 for a compound correspond in each case to one row of Table A
Table 148
Compounds of the formulae la, Ib, Ic, Id, le, If, Ig, Ih, li and Va in which Lnis 2,4-difluoro, R3 is cyano and R\ R2 for a compound correspond in each case to one row of Table A
Table 149
Compounds of the formulae la, Ib, Ic, Id, le, If, Ig, Ih, li and Va in which Ln is 2-fluoro-4-chloro, R3 is cyano and R1, R2 for a compound correspond in each case to one row of Table A
Table 150
Compounds of the formulae la, Ib, Ic, Id, le, If, Ig, Ih, li and Va in which Ln is 2-chloro-4-fluoro, R3 is cyano and R1, R2 for a compound correspond in each case to one row of Table A
Table 151
Compounds of the formulae la, Ib, Ic, Id, le, If, Ig, Ih, li and Va in which Lnis 2,3-difluoro, R3 is cyano and R1, R2 for a compound correspond in each case to one row of Table A
Table 152
Compounds of the formulae la, Ib, Ic, Id, le, If, Ig, Ih, li and Va in which Lnis 2,5-difluoro, R3 is cyano and R1, R2 for a compound correspond in each case to one row of Table A
Table 153

Compounds of the formulae la, Ib, Ic, Id, le, If, Ig, ih, li and Va in which Ln is 2,3,4-trifluoro, R3 is cyano and R1, R2 for a compound correspond in each case to one row of Table A
Table 154
Compounds of the formulae la, Ib, Ic, Id, le, If, Ig, Ih, li and Va in which Ln is 2-methyl,
R3 is cyano and R1, R2 for a compound correspond in each case to one row of Table A
Table 155
Compounds of the formulae la, Ib, Ic, Id, le, If, Ig, Ih, li and Va in which Lnis 2,4-dimethyl, R3 is cyano and R\ R2 for a compound correspond in each case to one row of Table A
Table 156
Compounds of the formulae la, Ib, Ic, Id, le, If, Ig, Ih, li and Va in which Lnis 2-methyl-4-chloro, R3 is cyano and R1, R2 for a compound correspond in each case to one row of Table A
Table 157
Compounds of the formulae la, Ib, Ic, Id, le, If, Ig, Ih, li and Va in which Ln is 2-fluoro-4-methyl, R3 is cyano and R1, R2 for a compound correspond in each case to one row of Table A
Table 158
Compounds of the formulae la, Ib, Ic, Id, le, If, Ig, Ih, li and Va in which Ln is 2,6-dimethyl, R3 is cyano and R1, R2 for a compound correspond in each case to one row of Table A
Table 159
Compounds of the formulae la, Ib, Ic, Id, le, If, Ig, Ih, li and Va in which Ln is 2,4,6-trimethyl, R3 is cyano and R1, R2 for a compound correspond in each case to one row of Table A
Table 160
Compounds of the formulae la, Ib, Ic, Id, le, If, Ig, Ih, li and Va in which Ln is 2,6-difluoro-4-cyano, R3 is cyano and R\ R2 for a compound correspond in each case to one row of Table A
Table 161

Compounds of the formulae la, Ib, Ic, Id, le, If, Ig, Ih, li and Va in which Ln is 2,6-difluoro-4-methyl, R3 is cyano and R\ R2 for a compound correspond in each case to one row of Table A
Table 162
Compounds of the formulae la, Ib, Ic, Id, le, If, Ig, Ih, li and Va in which Ln is 2,6-difluoro-4-methoxycarbonyl, R3 is cyano and R1, R2for a compound correspond in each case to one row of Table A
Table 163
Compounds of the formulae la, Ib, Ic, Id, le, If, Ig, Ih, li and Va in which Ln is 2-chloro, 4-methoxy, R3 is cyano and R1, R2 for a compound correspond in each case to one row of Table A
Table 164
Compounds of the formulae la, Ib, Ic, Id, le, If, Ig, Ih, li and Va in which Ln is 2-chloro, 4-methyl, R3 is cyano and R1, R2 for a compound correspond in each case to one row of Table A
Table 165
Compounds of the formulae la, Ib, Ic, Id, le, If, Ig, Ih, li and Va in which Ln is 2-chloro, 4-methoxycarbonyl, R3 is cyano and R1, R2 for a compound correspond in each case to one row of Table A
Table 166
Compounds of the formulae la, Ib, Ic, Id, le, If, Ig, Ih, li and Va in which Ln is 2-chloro, 4-bromo, R3 is cyano and R1, R2 for a compound correspond in each case to one row of Table A
Table 167
Compounds of the formulae la, Ib, Ic, Id, le, If, Ig, Ih, li and Va in which Ln is 2-chloro, 4-cyano, R3 is cyano and R1, R2 for a compound correspond in each case to one row of Table A
Table 168
Compounds of the formulae la, Ib, Ic, Id, le, If, Ig, Ih, li and Va in which Ln is 2,6-difluoro, 4-methoxy, R3 is cyano and R1, R2 for a compound correspond in each case to one row of Table A
Table 169

Compounds of the formulae la, Ib, Ic, Id, le, If, Ig, Ih, ii and Va in which Lnis 2-fluoro, 3-methyl, R3 is cyano and R\ R2 for a compound correspond in each case to one row of Table A
Table 170
Compounds of the formulae la, Ib, Ic, Id, le, If, Ig, Ih, Ii and Va in which Lnis 2,5-dimethyl, R3 is cyano and R1, R2 for a compound correspond in each case to one row of Table A
Table 171
Compounds of the formulae la, Ib, Ic, Id, le, If, Ig, Ih, Ii and Va in which Ln is 2-methyl, 4-cyano, R3 is cyano and R\ R2 for a compound correspond in each case to one row of Table A
Table 172
Compounds of the formulae la, Ib, Ic, Id, le, If, Ig, Ih, Ii and Va in which Ln is 2-methyl, 4-bromo, R3 is cyano and R\ R2 for a compound correspond in each case to one row of Table A
Table 173
Compounds of the formulae la, Ib, Ic, Id, le, If, Ig, Ih, Ii and Va in which Ln is 2-methyl, 5-fluoro, R3 is cyano and R1, R2 for a compound correspond in each case to one row of Table A
Table 174
Compounds of the formulae la, Ib, Ic, Id, le, If, Ig, Ih, Ii and Va in which Ln is 2-methyl, 4-methoxy, R3 is cyano and R1, R2 for a compound correspond in each case to one row of Table A
Table 175
Compounds of the formulae la, Ib, Ic, Id, le, If, Ig, Ih, Ii and Va in which Ln is 2-methyl, 4-methoxycarbonyl, R3 is cyano and R1, R2 for a compound correspond in each case to one row of Table A
Table 176
Compounds of the formulae la, Ib, Ic, Id, le, If, Ig, Ih, Ii and Va in which Ln is 2,5-dimethyl, 4-bromo, R3 is cyano and R1, R2 for a compound correspond in each case to one row of Table A
Table 177

Compounds of the formulae la, Ib, lct Id, le, If, Ig, Ih, li and Va in which Ln is 2-fluoro, 4-bromo, R3 is cyano and R1, R2 for a compound correspond in each case to one row of Table A
Table 178
Compounds of the formulae la, Ib, Ic, Id, le, If, Ig, Ih, li and Va in which Lnis 2-fluoro, 4-methoxy, R3 is cyano and R1, R2 for a compound correspond in each case to one row of Table A
Table 179
Compounds of the formulae la, Ib, Ic, Id, le, If, Ig, Ih, li and Va in which Lnis 2-fluoro, 5-methyl, R3 is cyano and R1, R2 for a compound correspond in each case to one row of Table A
Table 180
Compounds of the formulae la, Ib, Ic, Id, le, If, Ig, Ih, li and Va in which Ln is pentafluoro, R3 is cyano and R1, R2 for a compound correspond in each case to one row of Table A










Compounds of the formulae Ij and Ik in which R1 is CH2CF3i R2 is hydrogen and R3 is chloro and -X-Ra for a compound corresponds in each case to one row of Table B
Table 193
Compounds of the formulae Ij and Ik in which R1 is (R,S) CH(CH3)CH2CH3, R2 is hydrogen and R3 is chloro and -X-Ra for a compound corresponds in each case to one row of Table B
Table 194
Compounds of the formulae Ij and Ik in which R1 is (R) CH(CH3)CH2CH3, R2 is hydrogen and R3 is chloro and -X-Ra for a compound corresponds in each case to one row of Table B
Table 195
Compounds of the formulae Ij and Ik in which R1 is (S) CH(CH3)CH2CH3, R2 is hydrogen and R3 is chloro and -X-Ra for a compound corresponds in each case to one row of Table B
Table 196
Compounds of the formulae Ij and Ik in which R1 is (R,S) CH(CH3)CF3i R2 is hydrogen and R3 is chloro and -X-Ra for a compound corresponds in each case to one row of Table B
Table 197
Compounds of the formulae Ij and Ik in which R1 is (R) CH(CH3)CF3, R2 is hydrogen and R3 is chloro and -X-Ra for a compound corresponds in each case to one row of Table B
Table 198
Compounds of the formulae Ij and Ik in which R1 is (S) CH(CH3)CF3, R2 is hydrogen and R3 is chloro and -X-Ra for a compound corresponds in each case to one row of Table B
Table 199
Compounds of the formulae Ij and Ik in which NR1R2 is 4-methylpiperidine and R3 is
methoxy and -X-Ra for a compound corresponds in each case to one row of Table B
Table 200
Compounds of the formulae Ij and Ik in which R1 is CH(CH3)2, R2 is hydrogen and R3 is
methoxy and -X-Ra for a compound corresponds in each case to one row of Table B

Table 201
Compounds of the formulae Ij and Ik in which R1 is CH2CF3, R2 is hydrogen and R3 is
methoxy and -X-Ra for a compound corresponds in each case to one row of Table B
Table 202
Compounds of the formulae Ij and Ik in which R1 is (R,S) CH(CH3)CH2CH3, R2 is hydrogen and R3 is methoxy and -X-Ra for a compound corresponds in each case to one row of Table B
Table 203
Compounds of the formulae Ij and Ik in which R1 is (R) CH(CH3)CH2CH3, R2 is hydrogen and R3 is methoxy and -X-Ra for a compound corresponds in each case to one row of Table B
Table 204
Compounds of the formulae Ij and Ik in which R1 is (S) CH(CH3)CH2CH3, R2 is hydrogen and R3 is methoxy and -X-Ra for a compound corresponds in each case to one row of Table B
Table 205
Compounds of the formulae Ij and Ik in which R1 is (R,S) CH(CH3)CF3, R2 is hydrogen and R3 is methoxy and -X-Ra for a compound corresponds in each case to one row of Table B
Table 206
Compounds of the formulae Ij and Ik in which R1 is (R) CH(CH3)CF3, R2 is hydrogen and R3 is methoxy and -X-Ra for a compound corresponds in each case to one row of Table B
Table 207
Compounds of the formulae Ij and Ik in which R1 is (S) CH(CH3)CF3, R2 is hydrogen and R3 is methoxy and -X-Ra for a compound corresponds in each case to one row of Table B
Table 208
Compounds of the formulae Ij and Ik in which NR1R2 is 4-methylpiperidine and R3 is
cyano and -X-Ra for a compound corresponds in each case to one row of Table B
Table 209

Compounds of the formulae Ij and Ik in which R1 is CH(CH3)2, R2 is hydrogen and R3 is cyano and -X-Ra for a compound corresponds in each case to one row of Table B
Table 210
Compounds of the formulae Ij and Ik in which R1 is CH2CF3, R2 is hydrogen and R3 is
cyano and -X-Ra for a compound corresponds in each case to one row of Table B
Table 211
Compounds of the formulae Ij and Ik in which R1 is (R,S) CH(CH3)CH2CH3, R2 is hydrogen and R3 is cyano and -X-Ra for a compound corresponds in each case to one row of Table B
Table 212
Compounds of the formulae Ij and Ik in which R1 is (R) CH(CH3)CH2CH3, R2 is hydrogen and R3 is cyano and -X-Ra for a compound corresponds in each case to one row of Table B
Table 213
Compounds of the formulae Ij and Ik in which R1 is (S) CH(CH3)CH2CH3, R2 is hydrogen and R3 is cyano and -X-Ra for a compound corresponds in each case to one row of Table B
Table 214
Compounds of the formulae Ij and Ik in which R1 is (R,S) CH(CH3)CF3, R2 is hydrogen and R3 is cyano and -X-Ra for a compound corresponds in each case to one row of Table B
Table 215
Compounds of the formulae Ij and Ik in which R1 is (R) CH(CH3)CF3, R2 is hydrogen and R3 is cyano and -X-Ra for a compound corresponds in each case to one row of Table B
Table 216
Compounds of the formulae Ij and Ik in which R1 is (S) CH(CH3)CF3, R2 is hydrogen and R3 is cyano and -X-Ra for a compound corresponds in each case to one row of Table B
Table B







Mycosphaerella species on cereals, bananas and peanuts,
Phytophthora infestans on potatoes and tomatoes,
Plasmopara viticola on grapevines,
Podosphaera leucotricha on apples,
Pseudocercosporella herpotrichoides on wheat and barley,
Pseudoperonospora species on hops and cucumbers,
Puccinia species on cereals,
Pyricularia oryzae on rice,
Rhizoctonia species on cotton, rice and lawns,
Septoria triticiand Stagonospora nodorum on wheat,
Uncinula necator on grapevines,
Ustilago species on cereals and sugar cane, and
Venturia species (scab) on apples and pears.
The compounds I are also suitable for controlling harmful fungi, such as Paecilomyces variotii, in the protection of materials (for example wood, paper, paint dispersions, fibers or fabrics) and in the protection of stored products.
The compounds I are employed by treating the fungi or the plants, seeds, materials or soil to be protected against fungal attack with a fungicidally effective amount of the active compounds. The application can be carried out both before and after the infection of the materials, plants or seeds by the fungi.
The fungicidal compositions generally comprise between 0.1 and 95%, preferably between 0.5 and 90%, by weight of active compound.
When employed in plant protection, the amounts applied are, depending on the kind of effect desired, between 0.01 and 2.0 kg of active compound per ha.
In seed treatment, amounts of active compound of 0.001 to 0.1 g, preferably 0.01 to 0.05 g, per kilogram of seed are generally necessary.
When used in the protection of materials or stored products, the amount of active compound applied depends on the kind of application area and on the desired effect. Amounts customarily applied in the protection of materials are, for example, 0.001 g to 2 kg, preferably 0.005 g to 1 kg, of active compound per cubic meter of treated material.

The compounds I can be converted to the customary formulations, for example solutions, emulsions, suspensions, dusts, powders, pastes and granules. The application form depends on the particular intended use; it should in each case ensure a fine and uniform distribution of the compound according to the invention.
The formulations are prepared in a known manner, for example by extending the active compound with solvents and/or carriers, if desired using emulsifiers and dispersants. Solvents/auxiliaries which are suitable are essentially:
water, aromatic solvents (for example Solvesso products, xylene), paraffins (for example mineral oil fractions), alcohols (for example methanol, butanol, pentanol, benzyl alcohol), ketones (for example cyclohexanone, gamma-butyrolactone), pyrrolidones (NMP, NOP), acetates (glycol diacetate), glycols, fatty acid dimethylamides, fatty acids and fatty acid esters. In principle, solvent mixtures may also be used.
- carriers such as ground natural minerals (for example kaolins, clays, talc, chalk) and ground synthetic minerals (for example highly disperse silica, silicates); emulsifiers such as nonionic and anionic emulsifiers (for example polyoxyethylene fatty alcohol ethers, alkylsulfonates and arylsulfonates) and dispersants such as lignosulfite waste liquors and methylcellulose.
Suitable surfactants are alkali metal, alkaline earth metal and ammonium salts of lignosulfonicacid, naphthalenesulfonic acid, phenolsulfonicacid, dibutylnaphthalenesulfonic acid, alkylarylsulfonates, alkyl sulfates, alkylsulfonates, fatty alcohol sulfates, fatty acids and sulfated fatty alcohol glycol ethers, furthermore condensates of sulfonated naphthalene and naphthalene derivatives with formaldehyde, condensates of naphthalene or of naphthalenesulfonic acid with phenol and formaldehyde, polyoxyethylene octylphenyl ether, ethoxylated isooctylphenol, octylphenol, nonylphenol, alkylphenyl polyglycol ethers, tributylphenyl polyglycol ether, tristearylphenyl polyglycol ether, alkylaryl polyether alcohols, alcohol and fatty alcohol/ethylene oxide condensates, ethoxylated castor oil, polyoxyethylene alkyl ethers, ethoxylated polyoxypropylene, lauryl alcohol polyglycol ether acetal, sorbitol esters, lignosulfite waste liquors and methylcellulose.
Substances which are suitable for the preparation of directly sprayable solutions, emulsions, pastes or oil dispersions are mineral oil fractions of medium to high boiling point, such as kerosene or diesel oil, furthermore coal tar oils and oils of vegetable or

animal origin, aliphatic, cyclic and aromatic hydrocarbons, for example toluene, xylene, paraffin, tetrahydronaphthalene, alkylated naphthalenes or their derivatives, methanol, ethanol, propanol, butanol, cyclohexanol, cyclohexanone, isophorone, strongly polar solvents, for example dimethyl sulfoxide, N-methylpyrrolidone and water.
Powders, materials for spreading and dustable products can be prepared by mixing or concomitantly grinding the active substances with a solid carrier.
Granules, for example coated granules, impregnated granules and homogeneous granules, can be prepared by binding the active compounds to solid carriers. Examples of solid carriers are mineral earths such as silica gels, silicates, talc, kaolin, attaclay, limestone, lime, chalk, bole, loess, clay, dolomite, diatomaceous earth, calcium sulfate, magnesium sulfate, magnesium oxide, ground synthetic materials, fertilizers, such as, for example, ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas, and products of vegetable origin, such as cereal meal, tree bark meal, wood meal and nutshell meal, cellulose powders and other solid carriers.
In general, the formulations comprise from 0.01 to 95% by weight, preferably from 0.1 to 90% by weight, of the active compound. The active compounds are employed in a purity of from 90% to 100%, preferably 95% to 100% (according to NMR spectrum).
The following are examples of formulations: 1. Products for dilution with water
A) Water-soluble concentrates (SL)
10 parts by weight of a compound according to the invention are dissolved in water or in a water-soluble solvent. As an alternative, wetters or other auxiliaries are added. The active compound dissolves upon dilution with water.
B) Dispersible concentrates (DC)
20 parts by weight of a compound according to the invention are dissolved in cyclohexanone with addition of a dispersant, for example polyvinylpyrrolidone. Dilution with water gives a dispersion.
C) Emulsifiable concentrates (EC)

15 parts by weight of a compound according to the invention are dissolved in xylene with addition of calcium dodecylbenzenesulfonate and castor oil ethoxylate (in each case 5% strength). Dilution with water gives an emulsion.
D) Emulsions (EW, EO)
40 parts by weight of a compound according to the invention are dissolved in xylene with addition of calcium dodecylbenzenesulfonate and castor oil ethoxylate (in each case 5% strength). This mixture is introduced into water by means of an emulsifier (Ultraturvax) and made into a homogeneous emulsion. Dilution with water gives an emulsion.
E) Suspensions (SC, OD)
In an agitated ball mill, 20 parts by weight of a compound according to the invention are comminuted with addition of dispersants, wetters and water or an organic solvent to give a fine active compound suspension. Dilution with water gives a stable suspension of the active compound.
F) Water-dispersible granules and water-soluble granules (WG, SG)
50 parts by weight of a compound according to the invention are ground finely with addition of dispersants and wetters and made into water-dispersible or water-soluble granules by means of technical appliances (for example extrusion, spray tower, fluidized bed). Dilution with water gives a stable dispersion or solution of the active compound.
G) Water-dispersible powders and water-soluble powders (WP, SP)
75 parts by weight of a compound according to the invention are ground in a rotor-stator mill with addition of dispersants, wetters and silica gel. Dilution with water gives a stable dispersion or solution of the active compound.
2. Products to be applied undiluted H) Dusts (DP)
5 parts by weight of a compound according to the invention are ground finely and mixed intimately with 95% of finely divided kaolin. This gives a dustable product.

I) Granules (GR, FG, GG, MG)
0.5 part by weight of a compound according to the invention is ground finely and associated with 95.5% carriers. Customary methods are extrusion, spray-drying or the fluidized bed. This gives granules to be applied undiluted.
J) ULV solutions (UL)
10 parts by weight of a compound according to the invention are dissolved in an organic solvent, for example xylene. This gives a product to be applied undiluted.
The active compounds can be used as such, in the form of their formulations or of the application forms prepared therefrom, e.g. in the form of directly sprayable solutions, powders, suspensions or dispersions, emulsions, oil dispersions, pastes, dustable products, preparations for broadcasting or granules, by spraying, atomizing, dusting, broadcasting or watering. The application forms depend entirely on the intended uses; they should always ensure the finest possible dispersion of the active compounds according to the invention.
Aqueous application forms can be prepared from emulsifiable concentrates, pastes or wettable powders (spray powders, oil dispersions) by addition of water. To prepare emulsions, pastes or oil dispersions, the substances can be homogenized in water, as such or dissolved in an oil or solvent, by means of wetting agents, tackifiers, dispersants or emulsifiers. However, it is also possible to prepare concentrates comprising active substance, wetting agent, tackifier, dispersant or emulsifier and possibly solvent or oil which are suitable for dilution with water.
The concentrations of active compound in the ready-for-use preparations can be varied within relatively wide ranges. In general, they are between 0.0001 and 10%, preferably between 0.01 and 1%.
The active compounds can also be used with great success in the ultra-low volume (ULV) process, it being possible to apply formulations with more than 95% by weight of active compound or even the active compound without additives.
Oils of various types, wetting agents, adjuvants, herbicides, fungicides, other pesticides and bactericides can be added to the active compounds, if need be also not until

immediately before use (tank mix). These agents can be added to the preparations according to the invention in a weight ratio of 1:10 to 10:1.
The preparations according to the invention can, in the application form as fungicides, also be present together with other active compounds, e.g. with herbicides, insecticides, growth regulators, fungicides or also with fertilizers. On mixing the compounds I or the preparations comprising them in the application form as fungicides with other fungicides, in many cases an expansion of the fungicidal spectrum of activity is obtained.
The following list of fungicides, with which the compounds according to the invention can be used in conjunction, is intended to illustrate the possible combinations but does not limit them:
• acylalanines, such as benalaxyl, metalaxyl, ofurace oroxadixyl,
• amine derivatives, such as aldimorph, dodine, dodemorph, fenpropimorph,
fenpropidin, guazatine, iminoctadine, spiroxamine ortridemorph,
• anilinopyrimidines, such as pyrimethanil, mepanipyrim or cyprodinyl,
• antibiotics, such as cycloheximide, griseofulvin, kasugamycin, natamycin,
polyoxin or streptomycin,
• azoles, such as bitertanol, bromoconazole, cyproconazole, difenoconazole,
dinitroconazole, epoxiconazole, fenbuconazole, fluquinconazole, flusilazole,
flutriafol, hexaconazole, imazalil, metconazole, myclobutanil, penconazole,
propiconazole, prochloraz, prothioconazole, tebuconazole, triadimefon,
triadimenol, triflumizole ortriticonazole,
• dicarboximides, such as iprodione, myclozolin, procymidone or vinclozolin,
• dithiocarbamates, such as ferbam, nabam, maneb, mancozeb, metam, metiram,
propineb, polycarbamate, thiram, ziram orzineb,
• heterocyclic compounds, such as anilazine, benomyl, boscalid, carbendazim,
carboxin, oxycarboxin, cyazofamid, dazomet, dithianon, famoxadone,
fenamidone, fenarimol, fuberidazole, flutolanil, furametpyr, isoprothiolane,
mepronil,

nuarimol, probenazole, proquinazid, pyrifenox, pyroquilon, quinoxyfen, silthiofam, thiabendazole, thifluzamide, thiophanate-methyl, tiadinil, tricyclazole ortriforine,
• copper fungicides, such as Bordeaux mixture, copper acetate, copper
oxychloride or basic copper sulfate,
• nitrophenyl derivatives, such as binapacryl, dinocap, dinobuton or nitrophthal-
isopropyl,
• phenylpyrroles, such as fenpiclonil orfludioxonil,
• sulfur,
• other fungicides, such as acibenzolar-S-methyl, benthiavalicarb, carpropamid,
chlorothalonil, cyflufenamid, cymoxanil, dazomet, diclomezine, diclocymet,
diethofencarb, edifenphos, ethaboxam, fenhexamid, fentin acetate, fenoxanil,
ferimzone, fluazinam, fosetyl, fosetyl-aluminum, iprovalicarb, hexachlorobenzene,
metrafenone, pencycuron, propamocarb, phthalide, tolclofos-methyl, quintozene
or zoxamide,
• strobilurins, such as azoxystrobin, dimoxystrobin, fluoxastrobin, kresoxim-methyl,
metominostrobin, orysastrobin, picoxystrobin, pyraclostrobin ortrifloxystrobin,
• sulfenic acid derivatives, such as captafol, captan, dichlofluanid, folpet or
tolylfluanid,
• cinnamides and analogous compounds, such as dimethomorph, flumetover or
flumorph.
Synthesis examples



R1,R2 independently of one another are Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-
alkynyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, where the aliphatic group of the radical definitions of R1 and R2 for their part may be partially or fully halogenated or may carry one to four groups Rv:
Rv is cyano, C3-C6-cycloalkyl, C4-C6-cycloalkenyl, hydroxyl, CrC6-alkoxy, C2-C8-alkenyloxy, C2-C8-alkynyloxy, C3-C6-cycloalkyloxy, C4-C6-cycloalkenyloxy, Ci-C6-alkylthio, -C(=O)-A, -C(=O)-O-A, -C(=O)-N(A')A, C(A')(=N-OA), N(A')A, N(A')-C(=O)-A, N(A")-C(=O)-N(A')A, S(=O)m-A, S(=O)m-O-A or S(=O)m-N(A')A or phenyl, where the phenyl moiety may carry one to three radicals selected from the group consisting of: halogen, CrC6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, Ci-C6-haloalkyl, CrC6-alkoxy, cyano, nitro, -C(=O)-A, -C(=O)-O-A, -C(=O)-N(A')A, C(A')(-N-OA), N(A')A;
R2may additionally be hydrogen;
R1 and R2 may also, together with the nitrogen atom to which they are
attached, form a saturated or unsaturated five- or six-membered ring which may be interrupted by an ether (-O-), carbonyl (C=O), thio (-S-), sulfoxyl (-S[=O]-) or sulfenyl (-SOr-) or a further amino (-N(Ra) group, where Ra is hydrogen or CrCe-alkyl, and/or may contain one or more substituents from the group consisting of halogen, Ci-Ce-alkyI, Ci-Ce-haloalkyI and oxy-Ci-C3-alkyleneoxy;
R3 is halogen, cyano, CrC4-alkyl, C2-C4-alkenyl, C2-C4-alkynyl, C3-C6-cycloalkyl, C1-C4alkoxy, C3-C4-alkenyloxy, C3-C4-alkynyloxy, CrC6-alkylthio, di-(C1-C6-alkyl)amino or CrCe-alkylamino, where the alkyl, alkenyl and alkynyl radicals of R3 may be substituted by halogen, cyano, nitro, CrC2-alkoxy or CrC4-alkoxycarbonyl;











where the substituents Ln, R1, R2, R3, X and Ra are as defined in claim 1 and Hal is fluorine, chlorine, bromine or iodine.
11. A pesticide which comprises a solid or liquid carrier and a compound of the
formula I as claimed in claim 1.
12. A pesticide which comprises a solid or liquid carrier and a compound of the
formula V as claimed in either of claims 8 and 9.
13. A method for controlling phytopathogenic harmful fungi, which comprises treating
the fungi or the materials, plants, the soil or the seeds to be protected against
fungal attack with an effective amount of a compound of the formula I as claimed
in claim 1.
14. A method for controlling phytopathogenic harmful fungi, which comprises treating
the fungi or the materials, plants, the soil or the seeds to be protected against
fungal attack with an effective amount of a compound of the formula V as claimed
in either of claims 8 and 9.
c

Documents:

0644-chenp-2006 abstract duplicate.pdf

0644-chenp-2006 claims duplicate.pdf

0644-chenp-2006 description(complete) duplicate.pdf

644-CHENP-2006 CLAIMS GRANTED.pdf

644-CHENP-2006 CORRESPONDENCE OTHERS.pdf

644-CHENP-2006 CORRESPONDENCE PO.pdf

644-chenp-2006-abstract.pdf

644-chenp-2006-abstractimage.jpg

644-chenp-2006-claims.pdf

644-chenp-2006-correspondence-others.pdf

644-chenp-2006-desdcription(complete).pdf

644-chenp-2006-form 1.pdf

644-chenp-2006-form 26.pdf

644-chenp-2006-form 3.pdf

644-chenp-2006-form 5.pdf

644-chenp-2006-pct.pdf


Patent Number 229980
Indian Patent Application Number 644/CHENP/2006
PG Journal Number 13/2009
Publication Date 27-Mar-2009
Grant Date 24-Feb-2009
Date of Filing 22-Feb-2006
Name of Patentee BASF AKTIENGESELLSCHAFT
Applicant Address D-67056, Ludwigshafen,
Inventors:
# Inventor's Name Inventor's Address
1 SCHWOGLER, Anja Heinrich-Lanz-Strasse 3, 68165 Mannheim,
2 GEWEHR, Markus Goethestrasse 21, 56288 Kastellaun,
3 GRAMMENOS, Wassilios Alexander-Fleming-Strasse 13, 67071 Ludwigshafen,
4 TORMO I BLASCO, Jordi Carl-Benz-Strasse 10-3, 69514 Laudenbach,
5 GYPSER, Andreas B4, 4, 68159 Mannheim,
6 RHEINHEIMER, Joachim Merziger Strasse 24, 67063 Ludwigshafen,
7 BLETTNER, Carsten Richard-Wagner-Strasse 48, 68165 Mannheim,
8 SCHAFER, Peter Romerstrasse 1, 67308 Ottersheim,
9 SCHIEWECK, Frank Lindenweg 4, 67258 Hessheim,
10 WAGNER, Oliver Im Meisental 50, 67433 Neustadt,
11 SCHERER, Maria Hermann-Jurgens-Strasse 30, 76829 Godramstein,
12 STRATHMANN, Siegfried Donnersbergstrasse 9, 67117 Limburgerhof,
13 GROTE, Thomas Im Höhnhausen 18, 67157 Wachenheim,
14 SCHOFL, Ulrich Erlenstrasse 8, 68782 Bruhl,
15 MULLER, Bernd Stockingerstrasse 7, 67227 Frankenthal,
16 STIERL, Reinhard Jahnstrasse 8, 67251 Freinsheim,
PCT International Classification Number C07D239/42
PCT International Application Number PCT/EP2004/007877
PCT International Filing date 2004-07-15
PCT Conventions:
# PCT Application Number Date of Convention Priority Country
1 103 57 714.9 2003-12-09 Germany
2 103 33 857.8 2003-07-24 Germany