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(19)    (11) Patent Number: KE 313
1911:1111    (as} nit. avant. 27/04/2009
(12) PATENT
(51) Int.CLA: 01N 37/22, 37124, 43/56, 57/14, 01P 3/00
(21)Application    PCT/EP06/002779    (84) WO No. WO 2006/105889 A3
Number:    12/10/2006
(22)Filing Date:    02/10/2007
(31)Priority Number: 102005015850.1    (32) Date: (33) Country:
07/04/2005 DE
(73)    Owner(s):
Bayer Cropscience Aktiengesellschaft of , Alfred-Nobel-Str. 50, 40789 Monheim., Germany
(72) Inventor(s)    SUTY-IIEINZE, Anne; ELBE, Hans-Ludwig; SCHUTZ,
Burkhard and FEURER, Gerhard-Johann
(74)    Agent/address for correspondence: Kaplan & Stratton Advocates, P.O. Box 40111-00100, Nairobi
(54) Title:    SYNERGISTIC FUNGICIDAL ACTIVE SUBSTANCE COMBINATIONS.
(57) Abstract: The novel active substance combinations are produced from a carboxamide of general formula (I) (group 1), wherein A, R1 and R2 are defined as in the description, and active substance groups (2) and (3) listed in the description and have excellent fungicidal properties.
 
SvnernisAic funnicidal active compound combinations
The present invention relates to novel active compound combinations comprising, firstly, known carboxamides and, secondly, further known fungicidally active compounds, which combinations are 5    highly suitable for controlling unwanted phytopathogenic fungi.
It is already known that certain carboxamides have fungicidal properties: for example N-12-(1,3-dime-
thylbutyl)pheny11-5-fluoro-1,3-dimethy1-1H-pyrazole-4-carboxamide from WO 03/010149 and 3-(triflu-
orornethyl)-N4241,3-dimethylbuty0piteny11-5-fluoro-1-methyl-IH-pyrazole-4-carboxamide from DE-A
10 103 03 589. The activity of these compounds is good; however, at low application rates it is sometimes unsatisfactory. Furthermore, it is already known that numerous triazole derivatives, aniline derivatives, dicarboximides and other heterocycles can be used for controlling fungi (cf. EP-A 0 040 345, DE-A 22 01063, DE-A 23 24 010, Pesticide Manual, 9th Edition (1991), pages 249 and 827, EP-A 0 382 375 and EP-A 0 515 901). However, the activity of these compounds at low application rates is likewise not
15 always sufficient. Furthermore, it is already known that 1-(3,5-dimethylisozazole-4-sulphony1)-2-chloro¬6,6-difluoro-[1,3]-dicxolo44,5fibenzimidazole has fungicidal properties (cf. WO 97/06171). Finally, it is also known that substituted halopyrimidines have fungicidal properties (cf. DE-A1-196 46 407, EP-B-712 396).
20 This invention now provides novel active compound combinations having very good fungicidal properties and comprising at least one carboxamide of the general formula (I) (group 1)
 

 
Rr    represents hydrogen, halogen, C1-Cs-alkyl or Cr-Cs-haloalkyl having 1 to 7 fluorine, chorine
and/or bromine atoms,
25    A    represents one of the radicals Al to AS below:
A5
CS
0)C R°
R2    represents Cr-Cs-alkyl,    A2
AS    Rk
NY
Re
A7
io
CR,    A4
Re
A8
R9
0
 
-2-
R3    represents hydrogen, halogen, CFCs-alkyl or CFCs-haloalkyl having 1 to 7 fluorine, chlorine
and/or bromine atoms,
R4    represents hydrogen, halogen or CFCs-alkyl,
R'    represents halogen, CFCs-alkyl or C,C3-haloalkyl having 1 to 7 fluorine, chlorine and/or
5    bromine atoms,
R6    represents hydrogen, halogen, CFCs-alkyl, amino, mono- or di(CFC3-alkyl)amino,
R'    represents hydrogen, halogen, C5-C3-alkyl or C,-Cs-haloalkyl having l to 7 fluorine, chlorine
and/or bromine atoms,
R8    represents halogen, CFCs-alkyl or Cs-C3haloalkyl having 1 to 7 fluorine, chlorine and/or
10    bromine atoms,
R5    represents halogen, Ci-Cs-alkyl or C1-Cs-haloalkyl having I to 7 fluorine, chlorine and/or
bromine atoms,
R.1°    represents hydrogen, halogen, CFCs-alkyl or CL-Cs-haloalkyl having I. to 7 fluorine, chlorine
and/or bromine atoms,
15 and
(2)    tolclofos-methyl of the formula
H3C    CI     

(known from DE-A 25 01 040)
and/or
20    (3)    flutolanil of the formula
 
(known from DE-A 27 31 522).
Surprisingly, the fungicidal activity of the active compound combinations according to the invention is 25    considerably higher than the sum of the activities of the individual active compounds. Thus, an
unforeseeable true synergistic effect is present, and not just an addition of activities.
The formula (1) provides a general definition of the compounds of group (1).
30 Preference is given to carboxamides of the formula (1) in which
le    represents hydrogen, fluorine, chlorine, methyl, ethyl, n-propyl, isopropyl, monofluoromethyl,
 
-3-
difluoromethyl, trifluoromethyl, monochloromethyl, dichloromethyl or trichloromethyl, A    represents one of the radicals Al to A5 below:
     A2    A3    A4        A5
CO
 R9
        N
1=1'        R.   

R2    represents methyl, ethyl, n- or isopropyl,
5    R3    represents iodine, methyl, difluoromethyl or trifluoromethyl,
R4    represents hydrogen, fluorine, chlorine or methyl,
R5    represents chlorine, bromine, iodine, methyl, difluoromethyl or trifluoromethyl,
R6    represents hydrogen, chlorine, methyl, amino or dimethylamino,
112    represents methyl, difluoromethyl or trifluoromethyl,
1_0    125    represents bromine or methyl,
R9    represents methyl or trifluoromethyl.
N-licithrarazzo is given to carboxamides of the formula (I) in which
RI'    represents hydrogen, fluorine, chlorine, methyl, ethyl or trifluoromethyl,
15 A    represents one of the radicals Al or A2 below:
1.19 Al    A2
R4
I
R2    represents methyl or isopropyl,
R3    represents methyl, difluoromethyl or trifluoromethyl,
R4    represents hydrogen or fluorine,
20    R.5    represents iodine, difluoromethyl or trifluoromethyl.
Vg y particularpreference is given to carboxamides of the formula (I) in which
R.2    represents hydrogen or methyl,
A    represents one of the radicals Al or A2 below:
a AI    A2
NON    4
42
25
R2    represents methyl,
12.3    represents methyl,
 
- 4 -
R4    represents fluorine,
R5    represents iodine or trifluoromethyl.
Very particular preference is given to using, in mixtures, compounds of the formula (la),
5         (la)
    in which le. R2, R3 and R4 are as defined above.   

Very particular preference is given to using, in mixtures, compounds of the formula (lb)
 

 
10    in which R' and 115 are as defined above.
The formula (I) embraces in particular the following preferred mixing partners of group (1): (1-1) N42-(1,3-dimethylbutyl)pheny11-1,3-dimethy1-1H-pyrazole-4-carboxamide
(1-2) N-(2-6,3-dimethylbutyl)pheny1]-5-fluoro-1,3-dimethy1-1H-pyrazole-4-carboxamide
15    (known from WO 03/010149)
(1-3) N-12-0,3-dimethylbutyl)phertyl]-5-chloro-1,3-dimethyl-1H-pyrazole-4-carboxamide (known from JP-A 10-251240)
(1-4) 3-(difluoromethyl)-N42-(1,3-dimethylbutyl)pheny11-1-methy1-1H-pyrazole-4-carboxamide (1-5) 3-(trifluommethyl)-N42-(1,3-dimethylbutyl)pheny1]-5-fluoro-l-methyl-IH-pyrazole-
20    4-carboxamide (known from DE-A 103 03 589)
(1-6) 3-(trifluoromettly1)-N42-(1,3-dimethylbutyl)phenylj-5-chioro-l-methyl-1H-pyrazole-4-carboxamide (known from JP-A 10-251240)
(1-7) 1,3-dimethyl-N42-(1,3,3-trimethylbutyl)phenyl]- IH-pyrazole-4-carboxamide (known from JP-A 10-251240)
25    (1-8) 5-fluoro-1,3-dimethyl-N42-0,3,3-nimethylbutyl)pheny11-1H-pyrazole-4-carboxamide
(known from WO 03/010149)
(1-9) 3-(difluoromethyl)-1-methyl-N42-0,3,3-trimethylbutyl)phenyll-IH-pyrazole-4-carboxamide (1-10) 3-(trifluoromethyl)-1-methyl-N42-(1,3,3-trimethylbutyl)pheny1]-1H-pyrazole-4-carboxamide (1-11) 3-(trifluoromethyl)-5-fluoro-1-methyl-N42-(1,3,3-trimethylbutyl)pheny11-1H-pyrawle-
30    4-carboxamide (known from DE-A 103 03 589)
 
-5-
(1-12) 3-(tnfluoromethyl)-5-chloro- me thy l-N-12-( 1.,3,3-trimethy Ibutyl)pltny 11-111-pyrazo - 4-carboxamide (known from JP-A 10-251.240)
(1-13) N-[2-(1,3-dimethylbutyflpheny1]-2-iodobenzamide (known from DE-A 102 29 595)
(1-14) 2-iodo-N42-(1,3,3-trimethylbutyflphenyljbenzamide (known from DE-A 102 29 595)
5    (1-15) N-(2-(1,3-dimethy Ibutyl)pheny1]-2-(trifluoromethyl)benzamide
(known from DE-A 102 29 595)
(1-16) 2-(trifluommethyl)-N-[2-(1,3,3-trimethylbutyl)phenyl]benzamide
(known from DE-A 102 29 595)
10 Emphasis is given to active compound combinations according to the invention in which, in addition to the carboxamide (1-8) 5-fluoro-11,3-dimethyl-N-[2-(1,3,3-trirnethylbutyflphenyl]-1H-pyrazole-4-carbox¬amide (group 1) comprise one or more, preferably one, mixing partner of groups (2) and (3).
Emphasis is given to active compound combinations according to the invention in which, in addition to 15    the carboxamide (1-2) N-(2-(1,3-dimethylbutyl)phenyfl-5-fluoro-1,3-dimethyl-1H-pyrazole-4-carbox-
amide (group 1) comprise one or more, preferably one, mixing partner of groups (2) and (3).
Emphasis is given to active compound combinations according to the invention in which, in addition to the carboxamide (1-15) N-[2-(1,3-dirnethylbutyflpheny1]-2-(trifluoromethypbenzamide (group 1) corn 20 prise one or MOM, preferably one, mixing partner of groups (2) and (3).
Emphasis is given to active compound combinations according to the invention in which, in addition to the carboxamide (1-13) N-(2-(1,3-dimethylbutyflpheny1]-2-iodobenzamide (group 1) comprise one or more, preferably one, mixing partner of groups (2) and (3).
What is described below am preferred active compound combinations comprising two groups of active compounds and in each case at least one carboxamide of the formula (I) (group l) and at least one active compound of the stated group (2) and (3). These combinations are the active compound combinations A and B.
From among the preferred active compound combinations A and B, emphasis is given to those comprising a carboxamide of the formula (I) (group 1)
 
-6-
in which R' and A are as defined above.
Particular preference is given to active compound combinations A and B comprising a carboxamide of the formula (I) (group 1)
5
in which
R1    represents hydrogen, fluorine, chlorine, methyl, ethyl or trifluoromethyl,
A    represents one of the radicals Al or A2 below:
Al    A2
3
N,
IZ
10    R2    represents methyl,
R3    represents methyl, difluoromethyl or trifluoromethyl,
R"    represents hydrogen or fluorine,
R5    represents iodine or trifluoromethyl.
15 Very particular preference is given to active compound combinations A and B in which the carboxamide of the formula (I) (group 1) is selected from the list below:
(1- I ) N42-(11,3-dimethyIbutyl)pheny11-1,3-dimethyl-IH-pyrazole-4-carboxamide
(1-2) N42-(1,3-dimethylbutyl)pheny11-5-fluoro-1,3-dimethyl-1H-pyrazole-4-carboxamide
(1-3) N-[2-(1.,3-dimethylbutypphenyl]-5-ehloro-1,3-dimethyl-IH-pyrazole-4-carboxamide
20        (1-4) 3-(difluoromethyl)-N-(2-(1,3-dimethylbutyl)phenyl]-1-methyl-IH-pyrawle-4-carboxamide
(l-5) 3-(trifluoromethyl)-N12-(1,3-dimethylbutyl)plieny11-5-fluoro-l-mekl-111-PYrazole-
4-carboxarnide
(1-6) 3-(trifluoromethyl)-N-[2-(1,3-dimethylbutyl)pheny1]-5-c hloro-l-methy1-111-pyrazole¬4-carboxamide
25    (1-7) 1,3-dimethyl-N-12-(1,3,3-trimethylbuty0pheny11-1H-pyrazole-4-carboxamide
(1-8) 5-fluoro-1,3-dimethyl-N-[2-(1.,3,3-trimethylbutyl)pheny1]-1H-pyrazole-4-carboxamide
(1-9) 3-(difluoromethyl)-1-methyl-N-[2-(1,3,3-trimethylbutyl)phenyi]-1H-pyrazole-4-carboxamide (1-10) 3-(trifluoromethyl)-I-methyl-N-[2-(1,3,3-trimethylbutyl)phenyl]-IH-pyrazole-4-carboxamide
 
-7-
(1-11) 3-(trifluoromethyl)-5-fluoro- 1 -methyl-N42-(1,3,3-trimethyibutyl)pheny11-1H-pyrazole¬4-carboxamide
(1-12) 3-(trifluoromethyl)-5-chloro-l-methyl-N-(2-(1,3,3-trimethylbutyl)pheny1]-1H-pyrazole-4-carboxamide
5    (1-13) N12-(1,3-dimethylbutyl)phenyli-2-iodobenzamide
(1-14) 2-iodo-N-12-(1,3,3-trimethylbutyl)phenyilbenzamide
(1-15) N-12-(1,3-dimethylbutyl)phenyll-2-(trifluoromethyl)benzamide
(1-16) 2-(trifluoromethyl)-N[2-(1,3,3-trimethylbutyl)phenyl]benzamide
10 Especially preferred are active compound combinations A and B in which the carboxamide of the formula (1) (group 1) is selected from the list below:
(1-2) N42-(1,3-dimethylbutyl)pheny1]-5-fluoro-1,3-dimethy1-1H-pyrazole-4-carboxamide (1-8) 5-fluoro-1,3-dimethyl-N-12-(1,3,3-trimethylbutyi)pheny11-1H-pyrazole-4-carboxamide (1-10) 3-(trifluoromethyl)-1-methyl-N-[24 I,3,3-trimethylbutyl)pheny1]-1H-pyrazole-4-carboxamide
15    (1-13) N42-(i,3-dimethylbutyl)pheny11-2-iodobenzamide
(1-14) 2-iodo-N-(2-(1,3,3-trimethylbuty)phenylIbenzamide
(1-15) N-[2-(1,3-dimethylbutyl)phenyl]-2-(trifluoromethyl)benzamide
(1-16) 2-(trifluoromethyl)-N-[2-(1,3,3-trimethylbutyl)phenyl]benzamide
20 In addition to a carboxamide of the formula (I) (group 1), the active compound combinations A also comprise
(2)    tolclofos-methyl of the formula
0,1- ,
1;'CH,
H,C    CI O,CH,
25    Emphasis is given to the active compound combinations A listed in Table 1 below:
Table 1: Active compound combinations A
No.    Carboxamide of the formula (1)    Mixing partner
A-1    ( l -2) N42-(1,3-dimethylbutyl)pheny11-5-fluoro- l ,3-dimethyi¬1H-pyrazole-4-carboxamide    (2) tolciofos-methyl
A-2    (1-8) 5-fluoro-1,3-dimethyl-N-12-(1,3,3-trimethylbutyl)phenyll¬1H-pyrazole-4-carboxamide    (2) tolclofos-methyl
A-3    (1-10) 3-(trifluoromethyl)- l -methyl-N42-(1,3,3-trimethylbutyl)phenyll¬1H-pyrazole-4-carboxamide    (2) tolclofos-methyl
A-4    (1-13) N-[2-(1,3-dimethylbutyl)pheny1]-2-iodobenzamide    (2) tolclofos-methyl
A-5    (1-14) 2-iodo-N[2{i,3,3-trimethylbutyl)phenylThenzamide    (2) tolclofos-methyl
A-6    ( 1 -15) N12-(1,3-dirriethylbutyl)phenyl]-2-(tritluoromethyl)benzamide    (2) tolclofos-methyl
 
-8-
Table is Active compound combinations A
No.    Carboxamide of the formula (I)    Mixing partner
A-7    (1-16) 2-(trifluoromethyl)-N-12-( l 3,3-trimethylbutyl)phenyllbenzarnide    (2) tolclofos-methyl

In addition to a carboxamide of the formula (I) (group 1), the active compound combinations B also comprise
(3)    flutolanil of the formula
5         0    CI-13

Emphasis is given to the active compound combinations B listed in Table 2 below: Table 2: Active compound combinations B
No.    '    Carboxamide of the formula (I)    Mixing partner
B-1    (1-2) N-[2-(1,3-dimethylbutyl)phenyl]-5-fl uoro-1,3-dimethyl¬I H-pyrazole-4-carboxamide    (3) flutolanil
B-2    (1-8) 5-fluoro-1,3-dimethyl-N-12-(1,3,3-trimethylbutyl)phenyll¬IH-pyrazole-4-carboxamide    (3) flutolanil
13-3    (1-10) 3-(trifluoromethyl)-1-methyl-N-12-(1,3,3-trimethy Ibutyl)phenylj¬IH-pyrazole-4-carboxamide    (3) flutolanil
B-4    (1-13) N-12-(1,3-dimethylbutyl)pheny11-2-iodobenzamide    (3) flutolanil
B-5    (1-14) 2-iodo-N-12-(1,3,3-trimethylbutyl)phenyllbenzamide    (3) flutolanil
B-6    (1-15) N42-(1,3-dimethylbutyl)pheny1]-2-Mitluoromethylibenzarnide    (3) flutolanil
B-7    (1-16) 2-(trifluoromethyl)-N42-(1,3,3-trimethylbutyl)phenylbenzamide    (3) flutolanil

In addition to an active compound of the formula (I), the active compound combinations according to 10 the invention comprise at least one active compound from among the compounds of groups (2) and (3). In addition, they may also comprise further fungicidally active added components.
The synergistic effect is particularly pronounced if the active compounds in the active compound
combinations according to the invention are present in certain weight ratios. However, the weight ratios
15 of the active compounds in the active compound combinations can be varied within a relatively wide range. In general, the combinations according to the invention comprise active compounds of the formula (1) and a mixing partner from one of the groups (2) and (3) in the mixing ratios given in an exemplary manner in Table 3 below.
20 The mixing ratios are based on weight ratios. The ratio is to be understood as meaning active compound of the formula (I):mixing partner.
 
-9-
Table 3: Mixing ratios
Mixing partner    preferred mixing ratio    particularly preferred mixing ratio
(2)    tolclofos-methyl    50 : I    to    1 : 50    10 : 1    to    I : 20
(3)    flutolanil    50 : 1    to    1 : 50    20 : 1    to    I: 20

In each case, the mixing ratio is to be chosen such that a synergistic mixture is obtained. The mixing ratios of the compound of the formula (I) and a compound from one of groups (2) and (3) may also vary between the individual compounds of a group.
5
The active compound combinations according to the invention have a strong microbicidal action and can be used for controlling unwanted microorganisms, such as fungi and bacteria, in crop protection and in the protection of materials.
10    In crop protection, fungicides can be used for controlling Plasmodiophoromycetes, Oomycetes,
Chytrithomycetes, Zygomycetes, Ascomycetes, Basidiomycetes and Deuteromycetes.
In crop protection, bactericides can be used for controlling Pseudomonadaceae, Rhizobiaceae, Enterobacteriaceae, Corynebacteriaceae and Streptomycetaceae.
15
Some pathogens causing fungal and bacterial diseases which come under the generic names listed above may be mentioned as examples, but not by way of limitation:
Diseases caused by powdery mildew pathogens, such as, for example, Blumeria species, such as, for example, Blumeria graminis;
20 Podosphaera species, such as, for example, Podosphaera leucotricha; Sphaerotheca species, such as, for example, Sphaerotheca fuliginea; Uncinula species, such as, for example, Uncinula aerator;
Diseases caused by rust disease pathogens, such as, for example,
25 Gymnosporangium species, such as, for example, Gymnosporangium sabinae
Hemileia species, such as, for example, Hemileia vastatrix;
Phakopsora species, such as, for example, Phakopsora pachyrhizi and Phakopsora meibomiae; Puccinia species, such as, for example, Puccinia recondite;
Uromyces species, such as, for example, Uromyces appendiculatus;
30
Diseases caused by pathogens from the group of the Oomycetes, such as, for example,
 
- 10-
Bremia species, such as, for example, Bremia lactucae;
Peronospora species, such as, for example, Peronospora pisi or P. brassicae; Phytophthora species, such as, for example Phytophthora infestans; Plasmopara species, such as, for example, Plasmopara viticola;
5    Pseudoperonospora species, such as, for example, Pseudoperonospora humuli or
Pseudoperonospora cubensis;
Pythium species, such as, for example, Pythium ultimum;
Leaf blotch diseases and leaf wilt diseases caused, for example, by
10        Alternaria species, such as, for example, Altemaria solani;
Cercospora species, such as, for example, Cercospora beticola;
Cladiosporium species, such as, for example, Cladiosporium cucumerinum; Cochliobolus species, such as, for example, Cochliobolus sativus
(conidia form: Drechslera, Syn: Helminthosporium);
15    Colletotrichum species, such as, for example, Colletotrichum lindemuthanium;
Cycloconium species, such as, for example, Cycloconium oleaginum; Diaporthe species, such as, for example, Diaporthe citri;
Elsinoe species, such as, for example, Elsinoe fawcettii;
Gl000sporium species, such as, for example, Gloeosporium laeticolor,
20    Glomerella species, such as, for example, Glomerella cingulata;
Guignardia species, such as, for example, Guignardia bidwelli; Leptosphaeria species, such as, for example, Leptosphaeria maculans; Magnaporthe species, such as, for example, Magnaporthe grisea;
Mycosphaerella species, such as, for example, Mycosphaerelle graminicola;
25    Phaeosphaeria species, such as, for example, Phaeosphaeria nodorum;
Pyrenophora species, such as, for example, Ppenophora Ceres; Ramularia species, such as, for example, Ramularia collo-cygni;
Rhynchosporium species, such as, for example, Rhynchosporium secalis; Septoria species, such as, for example, Septoria apii;
30 Typhula species, such as, for example, Typhula incamata; Venturia species, such as, for example, Venturia inaequalis;
Root and stem diseases caused, for example, by
Corticium species, such as, for example, Corticium graminearum; 35 Fusarium species, such as, for example, Fusarium oxyspontm;
Gaeumannomyces species, such as, for example, Gaeurnannomyces graminis;
 
Rhizoctonia species, such as, for example Rhizoctonia solani; Tapesia species, such as, for example, Tapesia acuformis; Thielaviopsis species, such as, for example, Thielaviopsis basicola;
5    Ear and panicle diseases (including maize cobs) caused, for example, by
Altemaria species, such as, for example, Alternaria spp.; Aspergillus species, such as, for example, Aspergillus flavus;
Cladosporium species, such as, for example, Cladosporium spp. such as Cladosporium cladosporioides; Claviceps species, such as, for example, Claviceps purpurea;
10 Fusarium species, such as, for example, Fusarium culmortn; Gibberella species, such as, for example, Gibberella zeae; Monographella species, such as, for example, Monographella nivalis;
Diseases caused by smut fungi, such as, for example,
15    Sphacelotheca species, such as, for example, Sphacelotheca reiliarm;
Tilletia species, such as, for example, Tilletia caries;
Urocystis species, such as, for example, Urocystis occults; Ustilago species, such as, for example, Ustilago nuda;
20 Fruit rot caused, for example, by
Aspergillus species, such as, for example, Aspergillus flavus;
Botrytis species, such as, for example, Botrytis cinema;
Penicillium species, such as, for example, Penicillium expansum and Penicillium purpurogenum; Sclerotinia species, such as, for example, Sclerotinia sclerotiorum;
25    Verticilium species, such as, for example, Vetticilium alboatrum;
Seed- and soil-borne rot and wilt diseases, and also diseases of seedlings, caused, for example, by Fusarium species, such as, for example, Fusarium culmorum;
Phytophthora species, such as, for example, Phytophthora cactorum;
30    Pythium species, such as, for example, Pythium ultimum;
Rhizoctonia species, such as, for example, Rhizoctonia solani; Sclemtium species, such as, for example, Sclemtium rolfsii;
Cancerous diseases, galls and witches' broom caused, for example, by 35    Nectria species, such as, for example, Nectria galligena;
 
- 12 -
Wilt diseases caused, for example, by
Monilinia species, such as, for example, Monilinia laxa;
Deformations of leaves, flowers and fruits caused, for example, by 5    Taphrina species, such as, for example, Taphrina deformans;
Degenerative diseases of woody plants caused, for example, by Esca species, such as, for example, Phaemoniella clamydospora;
10    Diseases of flowers and seeds caused, for example, by
Botrytis species, such as, for example, Botrytis cinerea;
Diseases of plant tubers caused, for example, by
Rhizoctonia species, such as, for example, Rhizoctonia solani;
15    Helminthosporium species, such as, for example, Helminthosporium solani;
Diseases caused by bacteriopathogens, such as, for example,
Xanthomonas species, such as, for example, Xanthomonas campestris pv. oryzae; Pseudomonas species, such as, for example, Pseudomonas syringae pv. lachrymans; 20 Erwinia species, such as, for example, Erwinia amylovora.
Preference is given to controlling the following diseases of soya beans;
fungal diseases on leaves, stems, pods and seeds caused, for example, by
altemaria leaf spot (Altemaria spec. atrans teauissima), anthracnose (Colletotrichum gloeosporoides
25 dematium var. truncatum), brown spot (Septoria glycines), cercospora leaf spot and blight (Cercospora kikuchii), choanephora leaf blight (Choanephom infundibulifera trispora (Syn.)), dactuliophora leaf spot (Dactuliophora glycines), downy mildew (Peronospora manshurica), drechslera blight (Drechslera glycini), frogeye leaf spot (Cercospora sojina), leptosphaerulina leaf spot (Leptosphaerulina trifolii), phyllostica leaf spot (Phyllosticta sojaecola), pod and stem blight (Phomopsis sojae), powdery mildew
30 (Microsphaera diffuse), pyrenochaeta leaf spot (Pyrenochaeta glycines), rhizoctonia aerial, foliage, and web blight (Rhizoctonia solani), rust (Phakopsora pachyrhizi), scab (Sphaceloma glycines), stemphylium leaf blight (Stemphylium botryosum), target spot (Corynespora cassiicola)
Fungal diseases on roots and the stem base caused, for example, by
35    black root rot (Calonectria crotalariae), charcoal rot (Ma.crophomina phaseolina), fusarium blight or
wilt, root rot, and pod and collar rot (Fusarium oxysporum, Fusarium orthoceras, Fusarium sernitectum,
 
- 13 -
Fusarium equiseti), mycoleptodiscus root rot (Mycoleptodiscus terrestris), neocosmospora (Neocosmopspora vasinfecta), pod and stem blight (Diaporthe phaseolorum), stem canker (Diaporthe phaseolorum var. caulivora), phytophthora rot (Phytophthora megasperma), brown stem rot (Phialophora gregata), pythium rot (Pythium aphanidermatum, Pythium irregulare, Pythium
5 debaryanum, Pythium myriotylum, Pythium ultimum), rhizoctonia root rot, stem decay, and damping-off (Rhizoctonia solani), sclerotinia stem decay (Sclerotinia sclerotiorum), sclerotinia Southern blight (Sclerotinia rolfsii), thielaviopsis root rot (Thielaviopsis basicola).
The fact that the active compound combinations are well tolerated by plants at the concentrations
10 required for controlling plant diseases permits a treatment of entire plants (above-ground parts of plants and roots), of propagation stock and seed, and of the soil. The active compound combinations according to the invention can be used for foliar application or else as seed dressings.
The fact that the active compounds which can be used are well tolerated by plants at the concentrations 15    required for controlling plant diseases permits a treatment of the seed. Accordingly, the active
compounds according to the invention can be used as seed dressings.
A large part of the damage to crop plants which is caused by phytopathogenic fungi occurs as early as
when the seed is attacked during storage and after the seed is introduced into the soil, as well as during
20 and immediately after germination of the plants. This phase is particularly critical since the roots and shoots of the growing plant are particularly sensitive and even minor damage can lead to the death of the whole plank Protecting the seed and the germinating plant by the use of suitable compositions is therefore of particularly great interest.
25 The control of phytopathogenic fungi which damage plants post-emergence is carried out primarily by treating the soil and the above-ground parts of plants with crop protection agents. Owing to the concerns regarding a possible impact of crop protection agents on the environment and the health of man and animals, there are efforts to reduce the amount of active compounds applied.
30 The control of phytopathogenic fungi by treating the seed of plants has been known for a long time and is subject-matter of continuous improvements. However, the treatment of seed entails a series of problems which cannot always be solved in a satisfactory manner. Thus, it is desirable to develop methods for protecting the seed and the germinating plant which dispense with the additional application of crop protection agents after sowing or after the emergence of the plants or where additional
35        application is at least considerably reduced. It is furthermore desirable to optimize the amount of active
compound employed in such a way as to provide maximum protection for the seed and the germinating
 
-14-
plant from attack by phytopathogenic fungi, but without damaging the plant itself by the active compound employed. In particular, methods for the treatment of seed should also take into consideration the intrinsic fungicidal properties of transgenic plants in order to achieve optimum protection of the seed and the germinating plant with a minimum of crop protection agents being employed.
5
The present invention therefore in particular also relates to a method for the protection of seed and germinating plants from attack by phytopathogenic fungi, by treating the seed with a composition according to the invention.
10    The invention likewise relates to the use of the compositions according to the invention for the treatment
of seed for protecting the seed and the germinating plant from phytopathogenic fungi.
Furthermore, the invention relates to seed which has been treated with a composition according to the invention so as to afford protection from phytopathogenic fungi.
15
One of the advantages of the present invention is that, because of the particular systemic properties of the compositions according to the invention, treatment of the seed with these compositions not only protects the seed itself, but also the resulting plants after emergence, from phytopathogenic fungi. In this manner, the immediate treatment of the crop at the time of sowing or shortly thereafter can be dispensed
20    with.
Furthermore, it must be considered as advantageous that the mixtures according to the invention can also be employed in particular in transgenic seed.
25    The compositions according to the invention are suitable for protecting seed of any plant variety which
is employed in agriculture, in the greenhouse, in forests or in horticulture. In particular, this takes the form of seed of cereals (such as wheat, barley, rye, millet and oats), maize, cotton, soya beans, rice, potatoes, sunflowers, beans, coffee, beet (for example sugar beet and fodder beet), peanuts, vegetables (such as tomatoes, cucumbers, onions and lettuce), lawn and ornamental plants. The treatment of seed of
30    cereals (such as wheat, barley, rye and oats), maize and rice is of particular importance.
In the context of the present invention, the composition according to the invention is applied to the seed
either alone or in a suitable formulation. Preferably, the seed is treated in a state which is stable enough
to avoid damage during treatment. In general, the seed may be treated at any point in time between
35 harvest and sowing. The seed usually used has been separated from the plant and freed from cobs,
shells, stalks, coats, hairs or the flesh of the fruit. Thus, for example, it is possible to use seed which has
 
- 15 -
been harvested, cleaned and dried to a moisture content of below 15% by weight. Alternatively, it is also possible to use seed which, after drying, has, for example, been treated with water and then dried again.
When treating the seed, care must generally be taken that the amount of the composition according to
5 the invention applied to the seed and/or the amount of further additives is chosen in such a way that the germination of the seed is not adversely affected, or that the resulting plant is not damaged. This must be borne in mind in particular in the case of active compounds which may have phytotoxic effects at certain application rates.
10    The compositions according to the invention can be applied directly, that is to say without comprising
further components and without having been diluted. In general, it is preferable to apply the composition to the seed in the form of a suitable formulation. Suitable formulations and methods for the treatment of seed are known to the skilled worker and are described, for example, in the following documents: US 4,272,417 A, US 4,245,432 A, US 4,808,430 A, US 5,876,739 A, US 2003/0176428 Al,
15 WO 2002/080675 AI, WO 2002/028186 A2.
The active compound combinations according to the invention are also suitable for increasing the yield of crops. In addition, they show reduced toxicity and are well tolerated by plants.
20    According to the invention, it is possible to treat all plants and parts of plants. Plants are to be
understood here as meaning all plants and plant populations, such as desired and undesired wild plants or crop plants (including naturally occurring crop plants). Crop plants can be plants which can be obtained by conventional breeding and optimization methods or by biotechnological and genetic engineering methods or combinations of these methods, including the transgenic plants and including
25 plant cultivars which can or cannot be protected by plant breeders' certificates. Parts of plants are to be understood as meaning all above-ground and below-ground parts and organs of plants, such as shoot, leaf, flower and root, examples which may be mentioned being leaves, needles, stems, trunks, flowers, fruit-bodies, fruits and seeds and also roots, tubers and rhizomes. Parts of plants also include harvested material and vegetative and generative propagation material, for example seedlings, tubers, rhizomes,
30    cuttings and seeds.
The treatment of the plants and parts of plants according to the invention with the active compounds is
carried out directly or by action on their environment, habitat or storage area according to customary
treatment methods, for example by dipping, spraying, evaporating, atomizing, broadcasting, brushing-on
35        and, in the case of propagation material, in particular in the case of seeds, furthermore by one- or
multilayer coating.
 
- 16 -
As already mentioned above, it is possible to treat all plants and their parts according to the invention. In a preferred embodiment, wild plant species and plant cultivars, or those obtained by conventional biolo¬gical breeding methods, such as crossing or protoplast fission, and parts thereof, are treated. In a further preferred embodiment, transgenic plants and plant cultivars obtained by genetic engineering methods, if
5        appropriate in combination with conventional methods (Genetically Modified Organisms), and parts
thereof, are treated, The term "parts" or "parts of plants" or "plant parts" has been explained above.
Particularly preferably, plants of the plant cultivars which are in each case commercially available or in use are treated according to the invention.
I 0
Depending on the plant species or plant cultivars, their location and growth conditions (soils, climate, vegetation period, diet), the treatment according to the invention may also result in superadditive ("synergistic") effects. Thus, for example, reduced application rates and/or a widening of the activity spectrum and/or an increase in the activity of the substances and compositions which can be used
15 according to the invention, better plant growth, better developed root systems, higher resistance of the plant species and plant cultivars, increased growth of the shoots, higher plant vitality, increased tole-rance to high or low temperatures, increased tolerance to drought or to water or soil salt content, increa¬sed flowering performance, easier harvesting, accelerated maturation, higher harvest yields, bigger fruit, higher plant heights, greener leaves, earlier flowering, better quality and/or a higher nutritional value of
20 the harvested products, higher sugar concentration in the fruits, better storage stability and/or processabi¬lity of the harvested products are possible which exceed the effects which were actually to be expected.
The transgenic plants or plant cultivars (i.e. those obtained by genetic engineering) which are preferably
to be treated according to the invention include all plants which, in the genetic modification, received
25 genetic material which imparted particularly advantageous useful properties ("traits") to these plants. Examples of such properties are better plant growth, increased tolerance to high or low temperatures, increased tolerance to drought or to water or soil salt content, increased flowering performance, easier harvesting, accelerated maturation, higher harvest yields, better quality and/or a higher nutritional value of the harvested products, better storage stability and/or processability of the harvested products. Further
30 and particularly emphasized examples of such properties are a better defence of the plants against animal and microbial pests, such as against insects, mites, phytopathogenic fungi, bacteria and/or viruses, and also increased tolerance of the plants to certain herbicidally active compounds. Examples of transgenic plants which may be mentioned ate the important crop plants, such as cereals (wheat, rice), maize, soya beans, potatoes, cotton, oilseed rape and also fruit plants (with the fruits apples, pears, citrus
35        fruits and grapes), and particular emphasis is given to maize, soya beans, potatoes, cotton and oilseed
rape. Traits that are emphasized are in particular increased defence of the plants against insects, by
 
- 17 -
toxins formed in the plants, in particular those formed in the plants by the genetic material from Bacillus thuringiensis (for example by the genes CrylA(a), CryIA(b), CryIA(c), CrylIA, CryITIA, Cry11182, Cry9c, Cry2Ab, Cry3Bb and CryIF and also combinations thereof) (hereinbelow referred to as ''Bt plants"). Traits that are furthermore particularly emphasized are the increased tolerance of the plants to
5 certain herbicidally active compounds, for example imidazolinones, sulphonylureas, glyphosate or phosphinotricin (for example the "PAT" gene). The genes which impart the desired traits in question can also be present in combination with one another in the transgenic plants. Examples of "Bt plants" which may be mentioned are maize varieties, cotton varieties, soya bean varieties and potato varieties which are sold under the trade names YIELD GARD® (for example maize, cotton, soya beans), KnockOut®
I0 (for example maize), Starlink® (eg maize), Bollgard® (cotton), Nucotn® (cotton) and NewLeaf® (potato). Examples of herbicide-tolerant plants which may be mentioned are maize varieties, cotton varieties and soya bean varieties which am sold under the trade names Roundup Ready® (tolerance to glyphosate, for example maize, cotton, soya beans), Liberty Link® (tolerance to phosphinotricin, for example oilseed rape), 1MT® (tolerance to imidazolinones) and STS® (tolerance to sulphonylureas, for
15 example maize). Herbicide-resistant plants (plants bred in a conventional manner for herbicide tole¬rance) which may be mentioned also include the varieties sold under the name Clearfield® (for example maize). Of course, these statements also apply to plant cultivars which have these genetic traits or genetic traits still to be developed, and which will be developed and/or marketed in the future.
20 Depending on their particular physical and/or chemical properties, the active compound combinations according to the invention can be converted into the customary formulations, such as solutions, emulsions, suspensions, powders, dusts, foams, pastes, soluble powders, granules, aerosols, suspoemulsion concentrates, natural and synthetic materials impregnated with active compound and microencapsulations in polymeric substances and in coating compositions for seed, and ULV cold and
25 warm fogging formulations.
These formulations are produced in a known manner, for example by mixing the active compounds or
active compound combinations with extenders, that is liquid solvents, liquefied gases under pressure,
and/or solid carriers, optionally with the use of surfactants, that is emulsifiers and/or dispersants, and/or
30 foam formers.
If the extender used is water, it is also possible to employ, for example, organic solvents as auxiliary
solvents. Essentially, suitable liquid solvents are: aromatics such as xylene, toluene or alkylnaphtha-
lenes, chlorinated aromatics or chlorinated aliphatic hydrocarbons such as chlorobenzenes, chloro-
35        ethylenes or methylene chloride, aliphatic hydrocarbons such as cyclohexane or paraffins, for example
petroleum fractions, mineral and vegetable oils, alcohols such as butane' or glycol and their ethers and
 
- 18 -
esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as dimethylformamide and dimethyl sulphoxide, or else water.
Liquefied gaseous extenders or carriers are to be understood as meaning liquids which are gaseous at 5    standard temperature and under atmospheric pressure, for example aerosol propellants such as butane,
propane, nitrogen and carbon dioxide.
Suitable solid carriers are: for example ammonium salts and ground natural minerals such as kaolin,
clays. talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, and ground synthetic
10 minerals such as finely divided silica, alumina and silicates. Suitable solid carriers for granules are: for example crushed and fractionated natural rocks such as calcite, marble, pumice, sepiolite and dolomite, or else synthetic granules of inorganic and organic meals, and granules of organic material such as sawdust, coconut shells, maize cobs and tobacco stalks. Suitable emulsifiers and/or foam formers are: for example nonionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters,
15 polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkylsulphonates, alkyl sulphates, arylsulphonates, or else protein hydrolysates. Suitable dispersants are: for example lignosulphite waste liquors and methykeliulose.
Tackifiers such as carboxymethylcellulose, natural and synthetic polymers in the form of powders,
20 granules or latexes, such as gum arabic, polyvinyl alcohol and polyvinyl acetate, or else natural phospholipids such as cephalins and lecithins and synthetic phospholipids can be used in the formulations, Other possible additives are mineral and vegetable oils.
It is possible to use colorants such as inorganic pigments, for example iron oxide, titanium oxide and
25 Prussian Blue, and organic dyestuffs such as alizarin dyestuffs, azo dyestuffs and metal phthalocyanine dyestuffs, and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.
The active compound content of the use forms prepared from the commercial formulations may be
30 varied within wide ranges. The concentration of active compound of the use forms for controlling animal pests, such as insects and acarids, may be from 0.0000001 to 95% by weight of active compound and is preferably from 0.0001 to 1% by weight. Application is in a customary manner adapted to the use forms.
35 The formulations for controlling unwanted phytopathogenic fungi generally comprise between 0.1 and 95% by weight of active compounds, preferably between 05 and 90%.
 
- 19 -
The active compound combinations according to the invention can be used as such, in the form of their formulations or as the use forms prepared therefrom, such as ready-to-use solutions, emulsifiable concentrates, emulsions, suspensions, wettable powders, soluble powders, dusts and granules. They are used in a customary manner, for example by watering (drenching), drip irrigation, spraying, atomizing,
5 broadcasting, dusting, foaming, spreading-on, and as a powder for dry seed treatment, a solution for seed treatment, a water-soluble powder for seed treatment, a water-soluble powder for slurry treatment, or by encrusting etc..
The active compound combinations according to the invention can, in commercial formulations and in
10 the use forms prepared from these formulations, be present as a mixture with other active compounds, such as insecticides, attractants, sterilants, bactericides, acaricides, nematicides, fungicides, growth regulators or herbicides.
When using the active compound combinations according to the invention, the application rates can be
15 varied within a relatively wide range, depending on the kind of application. In the treatment of parts of plants, the application rates of active compound combination are generally between 0.1 and 10 000 gala, preferably between 10 and 1000 g/ha. In the treatment of seed, the application rates of active compound combination are generally between 0,001 and 50 g per kilogram of seed, preferably between 0.01 and 10 g per kilogram of seed. In the treatment of the soil, the application rates of active compound
20 combination are generally between 0.1 and 10 000 gala, preferably between 1 and 5000 g/ha.
The active compound combinations can be used as such, in the form of concentrates or in the form of generally customary formulations, such as powders, granules, solutions, suspensions, emulsions or pastes.
The formulations mentioned can be prepared in a manner known per se, for example by mixing the active compounds with at least one solvent or diluent, emulsifier, dispersant and/or binder or fixative, water repellent, if desired desiccants and UV stabilizers, and, if desired, colorants and pigments and other processing auxiliaries.
The good fungicidal action of the active compound combinations according to the invention is demonstrated by the examples below. While the individual active compounds show weaknesses in their fungicidal action, the combinations show an action which exceeds a simple sum of actions.
 
- 20 -
A synergistic effect in the fungicides is always present when the fungicidal action of the active compound combinations exceeds the total of the action of the active compounds when applied individually.
5    The expected fungicidal action for a given combination of two active compounds can be calculated as
follows, according to S.R. Colby ("Calculating Synergistic and Antagonistic Responses of Herbicide Combinations", Weeds    15, 20-22):
If
10
X    is the efficacy when employing active compound A at an application rate of in Oa,
Y    is the efficacy when employing active compound B at an application rate of n g/ha and
15    E    is the efficacy when employing active compounds A and B at application rates of m and rt gAta,
then    E=X+Y- XxY
100
Here, the efficacy is determined in %. 0% means an efficacy which corresponds to that of the control, 20    whereas an efficacy of 100% means that no infection is observed.
If the actual fungicidal action exceeds the calculated value, the action of the combination is superadditive, i.e. a synergistic effect is present. In this case, the actually observed efficacy mast exceed the value calculated using the above formula for the expected efficacy (E),
 
- 21 -
UsefIgijin
Example A
5    Pyricularia oryzae test (in vitro) / microlitre plates
The micro test is carried out in microtitre plates using potato dextrose broth (PDB) as liquid test
medium. The active compounds are used as technical-grade a.i., dissolved in acetone, or as a
commercial formulation. For inoculation, a spore suspension of Pyricularia oryzae is used. After 4 days
10 of incubation in the dark and with shaking (10 Hz), the transparency of each filled cavity of the microtitre plates is determined with the aid of a spectrophotometer. 0% means an efficacy which corresponds to the growth in the controls, whereas an efficacy of 100% means that no fungal growth is observed.
15 The table below clearly shows that the activity found for the active compound combination according to
the invention is greater than the one which had been calculated, i.e. that a synergistic effect is present.
Table A
Pyricularia oryzae test (in vitro) / microtitre plates
Active compounds    Active compound
concentration in ppm
—    Efficacy
found*
—    in % calc.**
(1-2) N42-(1,3-dimethylbutyllphenyli¬5-fluon)-1,3-dimethyl-1H-pyrazole- 4-carboxamide    0.03    20   
(2) tolclofos-methyl    0.03    13   
(1-2) N-I2-(11,3-dimethylbutyl)pheny1]- 5 -fluoro-1,3-dimethy1-1H-pyrazole¬4-carboxamide + (2) tolclofos-methyl (1: 1)    0.03 -I- 0.03    55    30

found = activity found
cale, = activity calculated using Colby' s formula
 
- 22 -
Example B
Alternaria mall test (in vitro) / microtitre plates
5    The micro test is carried out in microtitre plates using potato dextrose broth (PDB) as liquid test
medium. The active compounds are used as technical-grade a.i., dissolved in acetone, or as a commercial formulation. For inoculation, a spore suspension of Alternaria mall is used. After 3 days of incubation in the dark and with shaking (10 Hz), the transparency of each filled cavity of the microtitre plates is determined with the aid of a spectrophotometer. 0% means an efficacy which corresponds to
10 the growth in the controls, whereas an efficacy of 100% means that no fungal growth is observed.
The table below clearly shows that the activity found for the active compound combination according to the invention is greater than the one which had been calculated, i.e. that a synergistic effect is present.
Table B
Alternaria mall test (in vitro) / microtitre plates
Active compounds
y    Active compound
concentration in ppm    Efficacy found*    in % calc..*
(1-2) N[2-(1,3-climethylbutyfipheny11- 5-fluoro-1,3-dimethy1-1H-pyrawle- 4-carboxamide    1    83   
(3) flutolanil    1    12   
(1-2) N42-(1,3-dimethylbutyl)pheny1]- 5-fluoro- l,3-dimethyl-.1H-pyrazole- 4-carboxamide + (3) flutolanil (1 : 1 )    1 + 1    96    85

found = activity found
can. = activity calculated using Colby's formula
 
- 23 -
Patent claims
I        Synergistic fungicidal active compound combinations comprising a carboxamide of the general
formula (I) (group 1)
5         H3    (I)

in which
Re    represents hydrogen, halogen, C,-C3alkyl or CL-C3haloalkyl having I to 7 fluorine,
chorine and/or bromine atoms,
A    represents one of the radicals Al to A8 below:
Al    A2
\
Rz
AS    AS
10    CH3
NJ'
Fe    represents C,-C3-alkyl,
R3    represents hydrogen, halogen, C,-C3-alkyl or C,C3-haloalkyl having l to 7 fluorine,
chlorine and/or bromine atoms,
R4    represents hydrogen, halogen or C1-C3-alkyl,
15    R5    represents halogen, CI-C3-alkyl or C1-C3-haloalicyl having 1 to 7 fluorine, chlorine
and/or bromine atoms,
R6    represents hydrogen, halogen, C1-C3-alkyl, amino, mono- or di(Ci-C3-alkyl)amino,
R9    represents hydrogen, halogen, C1-C3-alkyl or C,-C3haioalkyl having 1 to 7 fluorine,
chlorine and/or bromine atoms,
20    le    represents halogen, C,-Cs-alkyl or CI-C3haloalkyi having 1 to 7 fluorine, chlorine
and/or bromine atoms,
R9    represents halogen, C,-C3alkyl or C,-Cs-haloallcyl having Ito 7 fluorine, chlorine
and/or bromine atoms,
R'9    represents hydrogen, halogen, C1-C3-alkyl or C,-C3-haloalkyl having 1 to 7 fluorine,
25    chlorine and/or bromine atoms,
 
-24-
and
(2)    tolctofos-methyl of the formula
C4'°'CH 9
H,C    CI 0, CH,
and/or
5    (3)    flutolanil of the formula
CF, S    C~Ha
CHa
2.    Active compound combinations according to Claim I comprising a carboxamide of the general
formula (I) according to Claim 1 (group 1) in which
10    R'    represents hydrogen, fluorine, chlorine, methyl, ethyl, n-propyl, isopropyl, mono-
fluoromethyl, difluoromethyl, trifluoromethyl, monochloromethyl, dichloromethyl or trrehloromethyl,
A    represents one of the radicals Al to AS below:
Al    A2    A3    A4    AS
S
,
C.    . Ji,
Fl    0    F19
15    R2    represents methyl, ethyl, n- or isopropyl,
R3    represents iodine, methyl, difluoromethyl or trifluoromethyl,
R4    represents hydrogen, fluorine, chlorine or methyl,
R5    represents chlorine, bromine, iodine, methyl, difluoromethyl or trifluoromethyl,
l(    represents hydrogen, chlorine, methyl, amino or dimethylamino,
20    le    represents methyl, difluoromethyl or trifluoromethyl,
Re    represents bromine or methyl,
R9    represents methyl or trifluoromethyl,
3.    Active compound combinations according to Claim 1 comprising the carboxamide (1-8)
25    5-fluoro-1,34imethyl-N42-(1,3,3-trimethylbutyl)pheny1J-IF/-pyrazole-4-carboxamide (group 1)
and at least one active compound selected from the following groups (2) and (3) according to Claim 1.
 
- 25 -
4.    Active compound combinations according to Claim l comprising the carboxamide (1-2) N42-
(1,3-dimethylbutyl)pheny11-5-fluoro-1,3-dimethyl-IH-pyrazole-4-carboxamide (group I) and at least one active compound selected from the following groups (2) and (3) according to Claim 1.
5    5.    Active compound combinations according to Claim 1 comprising the carboxamide (1-15) N-12-
(1,3-dimethylbutyl)phenyI]-2-(trifluoromethyl)benzamide (group 1) and at least one active compound selected from the following groups (2) and (3) according to Claim I.
6.    Active compound combinations according to Claim 1 comprising the carboxamide (1-13) N-[2-
10    (1,3-dimethylbutyl)pheny1]-2-iodobenzamide (group I) and at least one active compound
selected from the following groups (2) and (3) according to Claim 1.
7.    Use of active compound combinations according to Claim 1 for controlling unwanted phytopathogenic fungi.
15
8.    Use of active compound combinations according to Claim 1 for treating seed.
9.    Use of active compound combinations according to Claim 1 for treating transgenic plants.
20    10.    Use of active compound combinations according to Claim 1 for treating seed of transgenic
plants.
11.    Seed treated with an active compound combination according to Claim 1.
25    12.    Method for controlling unwanted phytopathogenic fungi, characterized in that active compound
combinations according to Claim 1 are applied to the unwanted phytopathogenic fungi and/or their habitat and/or seed.
13.    Process for preparing fungicidal compositions, characterized in that active compound
30    combinations according to Claim I. are mixed with extenders and/or surfactants.
 
Synergistic fungicidal active compound combinations
Abstract
The novel active compound combinations comprising a carboxamide of the general formula (I) (group 1 )
 

 
in which
A, R' and R2 are as defused in the description,
and the active compound groups (2) and (3) listed in the description have very good fungicidal properties.
Peter Hime/PJH/P.TH/ADMIN
 
indexation.Ist QCOK tags.Ist

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