Synergistic fungicidal active substance combinations

Information

  • Patent Grant
  • 9844220
  • Patent Number
    9,844,220
  • Date Filed
    Tuesday, February 9, 2016
    8 years ago
  • Date Issued
    Tuesday, December 19, 2017
    6 years ago
Abstract
Novel active compound combinations comprising a carboxamide of the general formula (I) (group 1)
Description

The present invention relates to novel active compound combinations comprising firstly known carboxamides and secondly further known fungicidally active compounds, which novel active compound combinations are highly suitable for controlling unwanted phytopathogenic fungi.


It is already known that certain carboxamides have fungicidal properties. Thus, for example, N-(3′,4′-dichloro-5-fluoro-1,1′-biphenyl-2-yl)-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide is known from DE-A 102 15 292, 3-(trifluoromethyl)-N-{3′-fluoro-4′-[(E)-(methoxyimino)methyl]-1,1′-biphenyl-2-yl}-1-methyl-1H-pyrazole-4-carboxamide is known from WO 02/08197 and N-(3′,4′-dichloro-1,1′-biphenyl-2-yl)-5-fluoro-1,3-dimethyl-1H-pyrazole-4-carboxamide is known WO 00/14701. 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 01 063, 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 action of these compounds is likewise not always sufficient at low application rates. Furthermore, it is already known that 1-(3,5-dimethylisoxazole-4-sulphonyl)-2-chloro-6,6-difluoro-[1,3]-dioxolo-[4,5f]-benzimidazole 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 0 712 396).


The present invention now provides novel active compound combinations having very good fungicidal properties and comprising a carboxamide of the general formula (I) (group 1)




embedded image



in which

  • R1 represents hydrogen or fluorine,
  • R2 represents halogen, C1-C3-alkyl, C1-C3-haloalkyl having 1 to 7 fluorine, chlorine and/or bromine atoms, C1-C3-alkoxy, C1-C3-haloalkoxy having 1 to 7 fluorine, chlorine and/or bromine atoms or represents —C(R4)═N—OR5,
  • R3 represents hydrogen, halogen, C1-C3-alkyl or C1-C3-haloalkyl having 1 to 7 fluorine, chlorine and/or bromine atoms,
  • R4 represents hydrogen or methyl,
  • R5 represents C1-C5-alkyl, C1-C5-alkenyl or C1-C5-alkynyl,
  • A represents one of the radicals A1 to A7 below:




embedded image


  • R6 represents C1-C3-alkyl,

  • R7 represents hydrogen, halogen, C1-C3-alkyl or C1-C3-haloalkyl having 1 to 7 fluorine, chlorine and/or bromine atoms,

  • R8 represents hydrogen, halogen or C1-C3-alkyl,

  • R9 represents hydrogen, halogen, C1-C3-alkyl, amino, mono- or di(C1-C3-alkyl)amino,

  • R10 represents hydrogen, halogen, C1-C3-alkyl or C1-C3-haloalkyl having 1 to 7 fluorine, chlorine and/or bromine atoms,

  • R11 represents halogen, C1-C3-alkyl or C1-C3-haloalkyl having 1 to 7 fluorine, chlorine and/or bromine atoms,

  • R12 represents halogen, C1-C3-alkyl or C1-C3-haloalkyl having 1 to 7 fluorine, chlorine and/or bromine atoms,

  • R13 represents hydrogen, halogen, C1-C3-alkyl or C1-C3-haloalkyl having 1 to 7 fluorine, chlorine and/or bromine atoms,

  • and at least one active compound selected from groups (2) to (23) below:


    Group (2) Strobilurins of the General Formula (II)





embedded image



in which

  • A1 represents one of the groups




embedded image


  • A2 represents NH or O,

  • A3 represents N or CH,

  • L represents one of the groups





embedded image




    • where the bond marked with an asterisk (*) is attached to the phenyl ring,



  • R14 represents phenyl, phenoxy or pyridinyl, each of which is optionally mono- or disubstituted by identical or different substituents from the group consisting of chlorine, cyano, methyl and trifluoromethyl, or represents 1-(4-chlorophenyl)-pyrazol-3-yl or represents 1,2-propane-dione-bis(O-methyloxime)-1-yl,

  • R15 represents hydrogen or fluorine;


    Group (3) Triazoles of the General Formula (III)





embedded image



in which

  • Q represents hydrogen or SH,
  • m represents 0 or 1,
  • R16 represents hydrogen, fluorine, chlorine, phenyl or 4-chlorophenoxy,
  • R17 represents hydrogen or chlorine,
  • A4 represents a direct bond, —CH2—, —(CH2)2— or —O—,
  • A4 furthermore represents *—CH2—CHR20— or *—CH═CR20— where the bond marked with * is attached to the phenyl ring, and
    • R18 and R20 furthermore together represent —CH2—CH2—CH[CH(CH3)2]— or —CH2—CH2—C(CH3)2—,
  • A5 represents C or Si (silicon),
  • A4 further represents —N(R20)— and A5 furthermore together with R18 and R19 represents the group C═N—R21, in which case R20 and R21 together represent the group




embedded image



where the bond marked with * is attached to R20,

  • R18 represents hydrogen, hydroxyl or cyano,
  • R19 represents 1-cyclopropylethyl, 1-chlorocyclopropyl, C1-C4-alkyl, C1-C6-hydroxyalkyl, C1-C4-alkylcarbonyl, C1-C2-haloalkoxy-C1-C2-alkyl, trimethylsilyl-C1-C2-alkyl, monofluorophenyl or phenyl,
  • R18 and R19 furthermore together represent —O—CH2—CH(R21)—O—, —O—CH2—CH(R21)—CH2—, or —O—CH(2-chlorophenyl)-,
  • R21 represents hydrogen, C1-C4-alkyl or bromine;


    Group (4) Sulphenamides of the General Formula (IV)




embedded image



in which R22 represents hydrogen or methyl;


Group (5) Valinamides Selected from

  • (5-1) iprovalicarb
  • (5-2) N-[2-(4-{[3-(4-chlorophenyl)-2-propynyl]oxy}-3-methoxyphenyl)ethyl]-N2-(methylsulphonyl)-D-valinamide
  • (5-3) benthiavalicarb


    Group (6) Carboxamides of the General Formula




embedded image



in which

  • X represents 2-chloro-3-pyridinyl, represents 1-methylpyrazol-4-yl which is substituted in the 3-position by methyl or trifluoromethyl and in the 5-position by hydrogen or chlorine, represents 4-ethyl-2-ethylamino-1,3-thiazol-5-yl, represents 1-methylcyclohexyl, represents 2,2-dichloro-1-ethyl-3-methylcyclopropyl, represents 2-fluoro-2-propyl or represents phenyl which is mono- to trisubstituted by identical or different substituents from the group consisting of chlorine and methyl,
  • X furthermore represents 3,4-dichloroisothiazol-5-yl, 5,6-dihydro-2-methyl-1,4-oxathiin-3-yl, 4-methyl-1,2,3-thiadiazol-5-yl, 4,5-dimethyl-2-trimethylsilylthiophen-3-yl, 1-methylpyrrol-3-yl which is substituted in the 4-position by methyl or trifluoromethyl and in the 5-position by hydrogen or chlorine,
  • Y represents a direct bond, C1-C6-alkanediyl (alkylene) which is optionally substituted by chlorine, cyano or oxo or represents thiophenediyl,
  • Y furthermore represents C2-C6-alkenediyl (alkenylene),
  • Z represents hydrogen or the group




embedded image


  • Z furthermore represents C1-C6-alkyl,

  • A6 represents CH or N,

  • R23 represents hydrogen, chlorine, phenyl which is optionally mono- or disubstituted by identical or different substituents from the group consisting of chlorine and di(C1-C3-alkyl)aminocarbonyl,

  • R23 furthermore represents cyano or C1-C6-alkyl,

  • R24 represents hydrogen or chlorine,

  • R25 represents hydrogen, chlorine, hydroxyl, methyl or trifluoromethyl,

  • R25 furthermore represents di(C1-C3-alkyl)aminocarbonyl,

  • R23 and R24 furthermore together represent *—CH(CH3)—CH2—C(CH3)2— or *—CH(CH3)—O—C(CH3)2— where the bond marked with * is attached to R23;


    Group (7) Dithiocarbamates Selected from

  • (7-1) mancozeb

  • (7-2) maneb

  • (7-3) metiram

  • (7-4) propineb

  • (7-5) thiram

  • (7-6) zineb

  • (7-7) ziram


    Group (8) Acylalanines of the General Formula (VI)





embedded image



in which

  • * marks a carbon atom in the R or the S configuration, preferably in the S configuration,
  • R26 represents benzyl, furyl or methoxymethyl;


    Group (9): Anilinopyrimidines of the General Formula (VII)




embedded image



in which

  • R27 represents methyl, cyclopropyl or 1-propynyl;


    Group (10): Benzimidazoles of the General Formula (VIII)




embedded image



in which

  • R28 and R29 each represent hydrogen or together represent —O—CF2—O—,
  • R30 represents hydrogen, C1-C4-alkylaminocarbonyl or represents 3,5-dimethylisoxazol-4-ylsulphonyl,
  • R31 represents chlorine, methoxycarbonylamino, chlorophenyl, furyl or thiazolyl;


    Group (11): Carbamates of the General Formula (IX)




embedded image



in which

  • R32 represents n- or isopropyl,
  • R33 represents di(C1-C2-alkyl)amino-C2-C4-alkyl or diethoxyphenyl,
  • salts of these compounds also being included;


    Group (12): Dicarboximides Selected from
  • (12-1) captafol
  • (12-2) captan
  • (12-3) folpet
  • (12-4) iprodione
  • (12-5) procymidone
  • (12-6) vinclozolin


    Group (13): Guanidines Selected from
  • (13-1) dodine
  • (13-2) guazatine
  • (13-3) iminoctadine triacetate
  • (13-4) iminoctadine tris(albesilate)


    Group (14): Imidazoles Selected from
  • (14-1) cyazofamid
  • (14-2) prochloraz
  • (14-3) triazoxide
  • (14-4) pefurazoate


    Group (15): Morpholines of the General Formula (X)




embedded image



in which

  • R34 and R35 independently of one another represent hydrogen or methyl,
  • R36 represents C1-C14-alkyl (preferably C12-C14-alkyl), C5-C12-cycloalkyl (preferably C10-C12-cycloalkyl), phenyl-C1-C4-alkyl, which may be substituted in the phenyl moiety by halogen or
  • C1-C4-alkyl or represents acrylyl which is substituted by chlorophenyl and dimethoxyphenyl;


    Group (16): Pyrroles of the General Formula (XI)




embedded image



in which

  • R37 represents chlorine or cyano,
  • R38 represents chlorine or nitro,
  • R39 represents chlorine,
  • R38 and R39 furthermore together represent —O—CF2—O—;


    Group (17): Phosphonates Selected from
  • (17-1) fosetyl-Al
  • (17-2) phosphonic acid;


    Group (18): Phenylethanamides of the General Formula (XII)




embedded image



in which

  • R40 represents unsubstituted or fluorine-, chlorine-, bromine-, methyl- or ethyl-substituted phenyl, 2-naphthyl, 1,2,3,4-tetrahydronaphthyl or indanyl;


    Group (19): Fungicides Selected from
  • (19-1) acibenzolar-S-methyl
  • (19-2) chlorothalonil
  • (19-3) cymoxanil
  • (19-4) edifenphos
  • (19-5) famoxadone
  • (19-6) fluazinam
  • (19-7) copper oxychloride
  • (19-8) copper hydroxide
  • (19-9) oxadixyl
  • (19-10) spiroxamine
  • (19-11) dithianon
  • (19-12) metrafenone
  • (19-13) fenamidone
  • (19-14) 2,3-dibutyl-6-chlorothieno[2,3-d]pyrimidin-4(3H)-one
  • (19-15) probenazole
  • (19-16) isoprothiolane
  • (19-17) kasugamycin
  • (19-18) phthalide
  • (19-19) ferimzone
  • (19-20) tricyclazole
  • (19-21) N-({4-[(cyclopropylamino)carbonyl]phenyl}sulphonyl)-2-methoxybenzamide
  • (19-22) 2-(4-chlorophenyl)-N-{2-[3-methoxy-4-(prop-2-yn-1-yloxy)phenyl]ethyl}-2-(prop-2-yn-1-yloxy)acetamide


    Group (20): (Thio)Urea Derivatives Selected from
  • (20-1) pencycuron
  • (20-2) thiophanate-methyl
  • (20-3) thiophanate-ethyl


    Group (21): Amides of the General Formula (XIII)




embedded image



in which

  • A7 represents a direct bond or —O—,
  • A8 represents —C(═O)NH— or —NHC(═O)—,
  • R41 represents hydrogen or C1-C4-alkyl,
  • R42 represents C1-C6-alkyl;


    Group (22): Triazolopyrimidines of the General Formula (XIV)




embedded image



in which

  • R43 represents C1-C6-alkyl or C2-C6-alkenyl,
  • R44 represents C1-C6-alkyl,
  • R43 and R44 furthermore together represent C4-C5-alkanediyl (alkylene) which is mono- or disubstituted by C1-C6-alkyl,
  • R45 represents bromine or chlorine,
  • R46 and R50 independently of one another represent hydrogen, fluorine, chlorine or methyl,
  • R47 and R49 independently of one another represent hydrogen or fluorine,
  • R48 represents hydrogen, fluorine or methyl,


    Group (23): Iodochromones of the General Formula (XV)




embedded image



in which

  • R51 represents C1-C6-alkyl,
  • R52 represents C1-C6-alkyl, C2-C6-alkenyl or C2-C6-alkynyl.


Surprisingly, the fungicidal action of the active compound combinations according to the invention is considerably better 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 actions.


The formula (I) provides a general definition of the compounds of group (1).

  • Preference is given to carboxamides of the formula (I) in which
  • R1 represents hydrogen or fluorine,
  • R2 represents fluorine, chlorine, bromine, iodine, methyl, trifluoromethyl, trifluoromethoxy or represents —C(R4)═N—OR5,
  • R3 represents hydrogen, fluorine, chlorine, bromine, methyl or trifluoromethyl,
  • R4 represents hydrogen or methyl,
  • R5 represents C1-C5-alkyl,
  • A represents one of the radicals A1 to A7 below:




embedded image


  • R6 represents methyl,

  • R7 represents iodine, methyl, difluoromethyl or trifluoromethyl,

  • R8 represents hydrogen, fluorine, chlorine or methyl,

  • R9 represents hydrogen, chlorine, methyl, amino or dimethylamino,

  • R10 represents methyl, difluoromethyl or trifluoromethyl,

  • R11 represents chlorine, bromine, iodine, methyl, difluoromethyl or trifluoromethyl,

  • R12 represents bromine or methyl,

  • R13 represents methyl or trifluoromethyl.



Particular preference is given to carboxamides of the formula (I) in which

  • R1 represents hydrogen or fluorine,
  • R2 represents fluorine, chlorine, bromine, trifluoromethyl or represents —CH═N—OCH3,
  • R3 represents hydrogen, fluorine or chlorine,
  • A represents one of the radicals A1 to A5 below:




embedded image


  • R6 represents methyl,

  • R7 represents methyl, difluoromethyl or trifluoromethyl,

  • R8 represents hydrogen or fluorine,

  • R9 represents methyl,

  • R10 represents methyl, difluoromethyl or trifluoromethyl,

  • R11 represents iodine, difluoromethyl or trifluoromethyl,

  • R12 represents methyl,

  • R13 represents methyl or trifluoromethyl.



Very particular preference is given to carboxamides of the formula (I) in which

  • R1 represents hydrogen or fluorine,
  • R2 represents fluorine, chlorine, bromine, trifluoromethyl or represents —CH═N—OCH3,
  • R3 represents hydrogen, fluorine or chlorine,
  • A represents one of the radicals A1 or A2 below:




embedded image


  • R6 represents methyl,

  • R7 represents methyl, difluoromethyl or trifluoromethyl,

  • R8 represents hydrogen or fluorine,

  • R9 represents methyl,

  • R10 represents methyl, difluoromethyl or trifluoromethyl.



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




embedded image



in which R1, R2, R3, R6, R7 and R8 are as defined above.


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




embedded image



in which R1, R2, R3, R9 and R10 are as defined above.


The formula (I) embraces in particular the following preferred mixing partners of group (1):

  • (1-1) N-(3′,4′-dichloro-5-fluoro-1,1′-biphenyl-2-yl)-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide (known from WO 03/070705)
  • (1-2) 3-(difluoromethyl)-N-{3′-fluoro-4′-[(E)-(methoxyimino)methyl]-1,1′-biphenyl-2-yl}-1-methyl-1H-pyrazole-4-carboxamide (known from WO 02/08197)
  • (1-3) 3-(trifluoromethyl)-N-{3′-fluoro-4′-[(E)-(methoxyimino)methyl]-1,1′-biphenyl-2-yl}-1-methyl-1H-pyrazole-4-carboxamide (known from WO 02/08197)
  • (1-4) N-(3′,4′-dichloro-1,1′-biphenyl-2-yl)-5-fluoro-1,3-dimethyl-1H-pyrazole-4-carboxamide (known from WO 00/14701)
  • (1-5) N-(4′-chloro-3′-fluoro-1,1′-biphenyl-2-yl)-2-methyl-4-(trifluoromethyl)-1,3-thiazole-5-carboxamide (known from WO 03/066609)
  • (1-6) N-(4′-chloro-1,1′-biphenyl-2-yl)-4-(difluoromethyl)-2-methyl-1,3-thiazole-5-carboxamide (known from WO 03/066610)
  • (1-7) N-(4′-bromo-1,1′-biphenyl-2-yl)-4-(difluoromethyl)-2-methyl-1,3-thiazole-5-carboxamide (known from WO 03/066610)
  • (1-8) 4-(difluoromethyl)-2-methyl-N-[4′-(trifluoromethyl)-1,1′-biphenyl-2-yl]-1,3-thiazole-5-carboxamide (known from WO 03/066610)
  • (1-9) N-(4′-chloro-3′-fluoro-1,1′-biphenyl-2-yl)-4-(difluoromethyl)-2-methyl-1,3-thiazole-5-carboxamide (known from WO 03/066610)


Emphasis is given to active compound combinations according to the invention which, in addition to carboxamide (1-1) N-(3′,4′-dichloro-5-fluoro-1,1′-biphenyl-2-yl)-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide (group 1) comprise one or more, preferably one, mixing partner of groups (2) to (23).


Emphasis is given to active compound combinations according to the invention which, in addition to carboxamide (1-7) N-(4′-bromo-1,1′-biphenyl-2-yl)-4-(difluoromethyl)-2-methyl-1,3-thiazole-5-carboxamide (group 1) comprise one or more, preferably one, mixing partner of groups (2) to (23).


Emphasis is given to active compound combinations according to the invention which, in addition to carboxamide (1-8) 4-(difluoromethyl)-2-methyl-N-[4′-(trifluoromethyl)-1,1′-biphenyl-2-yl]-1,3-thiazole-5-carboxamide (group 1) comprise one or more, preferably one, mixing partner of groups (2) to (23).


Emphasis is given to active compound combinations according to the invention which, in addition to carboxamide (1-9) N-(4′-chloro-3′-fluoro-1,1′-biphenyl-2-yl)-4-(difluoromethyl)-2-methyl-1,3-thiazole-5-carboxamide (group 1) comprise one or more, preferably one, mixing partner of groups (2) to (23).


The formula (II) embraces the following preferred mixing partners of group (2):

  • (2-1) azoxystrobin (known from EP-A 0 382 375) of the formula




embedded image


  • (2-2) fluoxastrobin (known from DE-A 196 02 095) of the formula





embedded image


  • (2-3) (2E)-2-(2-{[6-(3-chloro-2-methylphenoxy)-5-fluoro-4-pyrimidinyl]oxy}phenyl)-2-(methoxy-imino)-N-methylethanamide (known from DE-A 196 46 407, EP-B 0 712 396) of the formula





embedded image


  • (2-4) trifloxystrobin (known from EP-A 0 460 575) of the formula





embedded image


  • (2-5) (2E)-2-(methoxyimino)-N-methyl-2-(2-{[({(1E)-1-[3-(trifluoromethyl)phenyl]ethylidene}-amino)oxy]methyl}phenyl)ethanamide (known from EP-A 0 569 384) of the formula





embedded image


  • (2-6) (2E)-2-(methoxyimino)-N-methyl-2-{2-[(E)-({1-[3-(trifluoromethyl)phenyl)ethoxy}imino)-methyl]phenyl}ethanamide (known from EP-A 0 596 254) of the formula





embedded image


  • (2-7) orysastrobin (known from DE-A 195 39 324) of the formula





embedded image


  • (2-8) 5-methoxy-2-methyl-4-(2-{[({(1E)-1-[3-(trifluoromethyl)phenyl]ethylidene}amino)oxy]-methyl}phenyl)-2,4-dihydro-3H-1,2,4-triazol-3-one (known from WO 98/23155) of the formula





embedded image


  • (2-9) kresoxim-methyl (known from EP-A 0 253 213) of the formula





embedded image


  • (2-10) dimoxystrobin (known from EP-A 0 398 692) of the formula





embedded image


  • (2-11) picoxystrobin (known from EP-A 0 278 595) of the formula





embedded image


  • (2-12) pyraclostrobin (known from DE-A 44 23 612) of the formula





embedded image


  • (2-13) metominostrobin (known from EP-A 0 398 692) of the formula





embedded image


The formula (III) embraces the following preferred mixing partners of group (3):

  • (3-1) azaconazole (known from DE-A 25 51 560) of the formula




embedded image


  • (3-2) etaconazole (known from DE-A 25 51 560) of the formula





embedded image


  • (3-3) propiconazole (known from DE-A 25 51 560) of the formula





embedded image


  • (3-4) difenoconazole (known from EP-A 0 112 284) of the formula





embedded image


  • (3-5) bromuconazole (known from EP-A 0 258 161) of the formula





embedded image


  • (3-6) cyproconazole (known from DE-A 34 06 993) of the formula





embedded image


  • (3-7) hexaconazole (known from DE-A 30 42 303) of the formula





embedded image


  • (3-8) penconazole (known from DE-A 27 35 872) of the formula





embedded image


  • (3-9) myclobutanil (known from EP-A 0 145 294) of the formula





embedded image


  • (3-10) tetraconazole (known from EP-A 0 234 242) of the formula





embedded image


  • (3-11) flutriafol (known from EP-A 0 015 756) of the formula





embedded image


  • (3-12) epoxiconazole (known from EP-A 0 196 038) of the formula





embedded image


  • (3-13) flusilazole (known from EP-A 0 068 813) of the formula





embedded image


  • (3-14) simeconazole (known from EP-A 0 537 957) of the formula





embedded image


  • (3-15) prothioconazole (known from WO 96/16048) of the formula





embedded image


  • (3-16) fenbuconazole (known from DE-A 37 21 786) of the formula





embedded image


  • (3-17) tebuconazole (known from EP-A 0 040 345) of the formula





embedded image


  • (3-18) ipconazole (known from EP-A 0 329 397) of the formula





embedded image


  • (3-19) metconazole (known from EP-A 0 329 397) of the formula





embedded image


  • (3-20) triticonazole (known from EP-A 0 378 953) of the formula





embedded image


  • (3-21) bitertanol (known from DE-A 23 24 010) of the formula





embedded image


  • (3-22) triadimenol (known from DE-A 23 24 010) of the formula





embedded image


  • (3-23) triadimefon (known from DE-A 22 01 063) of the formula





embedded image


  • (3-24) fluquinconazole (known from EP-A 0 183 458) of the formula





embedded image


  • (3-25) quinconazole (known from EP-A 0 183 458) of the formula





embedded image


The formula (IV) embraces the following preferred mixing partners of group (4):

  • (4-1) dichlofluanid (known from DE-A 11 93 498) of the formula




embedded image


  • (4-2) tolylfluanid (known from DE-A 11 93 498) of the formula





embedded image


Preferred mixing partners of group (5) are

  • (5-1) iprovalicarb (known from DE-A 40 26 966) of the formula




embedded image


  • (5-3) benthiavalicarb (known from WO 96/04252) of the formula





embedded image


The formula (V) embraces the following preferred mixing partners of group (6):

  • (6-1) 2-chloro-N-(1,1,3-trimethylindan-4-yl)nicotinamide (known from EP-A 0 256 503) of the formula




embedded image


  • (6-2) boscalid (known from DE-A 195 31 813) of the formula





embedded image


  • (6-3) furametpyr (known from EP-A 0 315 502) of the formula





embedded image


  • (6-4) N-(3-p-tolylthiophen-2-yl)-1-methyl-3-trifluoromethyl-1H-pyrazole-4-carboxamide (known from EP-A 0 737 682) of the formula





embedded image


  • (6-5) ethaboxam (known from EP-A 0 639 574) of the formula





embedded image


  • (6-6) fenhexamid (known from EP-A 0 339 418) of the formula





embedded image


  • (6-7) carpropamid (known from EP-A 0 341 475) of the formula





embedded image


  • (6-8) 2-chloro-4-(2-fluoro-2-methylpropionylamino)-N,N-dimethylbenzamide (known from EP-A 0 600 629) of the formula





embedded image


  • (6-9) picobenzamid (known from WO 99/42447) of the formula





embedded image


  • (6-10) zoxamide (known from EP-A 0 604 019) of the formula





embedded image


  • (6-11) 3,4-dichloro-N-(2-cyanophenyl)isothiazole-5-carboxamide (known from WO 99/24413) of the formula





embedded image


  • (6-12) carboxin (known from U.S. Pat. No. 3,249,499) of the formula





embedded image


  • (6-13) tiadinil (known from U.S. Pat. No. 6,616,054) of the formula





embedded image


  • (6-14) penthiopyrad (known from EP-A 0 737 682) of the formula





embedded image


  • (6-15) silthiofam (known from WO 96/18631) of the formula





embedded image


  • (6-16) N-[2-(1,3-dimethylbutyl)phenyl]-1-methyl-4-(trifluoromethyl)-1H-pyrrole-3-carboxamide (known from WO 02/38542) of the formula





embedded image


Preferred mixing partners of group (7) are

  • (7-1) mancozeb (known from DE-A 12 34 704) having the IUPAC name manganese ethylenebis(dithiocarbamate) (polymeric) complex with zinc salt
  • (7-2) maneb (known from U.S. Pat. No. 2,504,404) of the formula




embedded image


  • (7-3) metiram (known from DE-A 10 76 434) having the IUPAC name zinc ammoniate ethylenebis(dithiocarbamate)-poly(ethylenethiuram disulphide)

  • (7-4) propineb (known from GB 935 981) of the formula





embedded image


  • (7-5) thiram (known from U.S. Pat. No. 1,972,961) of the formula





embedded image


  • (7-6) zineb (known from DE-A 10 81 446) of the formula





embedded image


  • (7-7) ziram (known from U.S. Pat. No. 2,588,428) of the formula





embedded image


The formula (VI) embraces the following preferred mixing partners of group (8):

  • (8-1) benalaxyl (known from DE-A 29 03 612) of the formula




embedded image


  • (8-2) furalaxyl (known from DE-A 25 13 732) of the formula





embedded image


  • (8-3) metalaxyl (known from DE-A 25 15 091) of the formula





embedded image


  • (8-4) metalaxyl-M (known from WO 96/01559) of the formula





embedded image


  • (8-5) benalaxyl-M of the formula





embedded image


The formula (VII) embraces the following preferred mixing partners of group (9):

  • (9-1) cyprodinil (known from EP-A 0 310 550) of the formula




embedded image


  • (9-2) mepanipyrim (known from EP-A 0 270 111) of the formula





embedded image


  • (9-3) pyrimethanil (known from DD 151 404) of the formula





embedded image


The formula (VIII) embraces the following preferred mixing partners of group (10):

  • (10-1) 6-chloro-5-[(3,5-dimethylisoxazol-4-yl)sulphonyl]-2,2-difluoro-5H-[1,3]dioxolo[4,5-f]-benzimidazole (known from WO 97/06171) of the formula




embedded image


  • (10-2) benomyl (known from U.S. Pat. No. 3,631,176) of the formula





embedded image


  • (10-3) carbendazim (known from U.S. Pat. No. 3,010,968) of the formula





embedded image


  • (10-4) chlorfenazole of the formula





embedded image


  • (10-5 fuberidazole (known from DE-A 12 09 799) of the formula





embedded image


  • (10-6) thiabendazole (known from U.S. Pat. No. 3,206,468) of the formula





embedded image


The formula (IX) embraces the following preferred mixing partners of group (11):

  • (11-1) diethofencarb (known from EP-A 0 078 663) of the formula




embedded image


  • (11-2) propamocarb (known from U.S. Pat. No. 3,513,241) of the formula





embedded image


  • (11-3) propamocarb-hydrochloride (known from U.S. Pat. No. 3,513,241) of the formula





embedded image


  • (11-4) propamocarb-fosetyl of the formula





embedded image


Preferred mixing partners of group (12) are

  • (12-1) captafol (known from U.S. Pat. No. 3,178,447) of the formula




embedded image


  • (12-2) captan (known from U.S. Pat. No. 2,553,770) of the formula





embedded image


  • (12-3) folpet (known from U.S. Pat. No. 2,553,770) of the formula





embedded image


  • (12-4) iprodione (known from DE-A 21 49 923) of the formula





embedded image


  • (12-5) procymidone (known from DE-A 20 12 656) of the formula





embedded image


  • (12-6) vinclozolin (known from DE-A 22 07 576) of the formula





embedded image


Preferred mixing partners of group (13) are

  • (13-1) dodine (known from GB 11 03 989) of the formula




embedded image


  • (13-2) guazatine (known from GB 11 14 155)

  • (13-3) iminoctadine triacetate (known from EP-A 0 155 509) of the formula





embedded image


Preferred mixing partners of the group (14) are

  • (14-1) cyazofamid (known from EP-A 0 298 196) of the formula




embedded image


  • (14-2) prochloraz (known from DE-A 24 29 523) of the formula





embedded image


  • (14-3) triazoxide (known from DE-A 28 02 488) of the formula





embedded image


  • (14-4) pefurazoate (known from EP-A 0 248 086) of the formula





embedded image


The formula (X) embraces the following preferred mixing partners of group (15):

  • (15-1) aldimorph (known from DD 140 041) of the formula




embedded image


  • (15-2) tridemorph (known from GB 988 630) of the formula





embedded image


  • (15-3) dodemorph (known from DE-A 25 432 79) of the formula





embedded image


  • (15-4) fenpropimorph (known from DE-A 26 56 747) of the formula





embedded image


  • (15-5) dimethomorph (known from EP-A 0 219 756) of the formula





embedded image


The formula (XI) embraces the following preferred mixing partners of group (16):

  • (16-1) fenpiclonil (known from EP-A 0 236 272) of the formula




embedded image


  • (16-2) fludioxonil (known from EP-A 0 206 999) of the formula





embedded image


  • (16-3) pyrrolnitrin (known from JP 65-25876) of the formula





embedded image


Preferred mixing partners of group (17) are

  • (17-1) fosetyl-Al (known from DE-A 24 56 627) of the formula




embedded image


  • (17-2) phosphonic acid (known chemical) of the formula





embedded image


The formula (XII) embraces the following preferred mixing partners of group (18) which are known from WO 96/23793 and can in each case be present as E or Z isomers. Accordingly, compounds of the formula (XII) can be present as a mixture of different isomers or else in the form of a single isomer. Preference is given to compounds of the formula (XII) in the form of their E isomers:

  • (18-1) 2-(2,3-dihydro-1H-inden-5-yl)-N-[2-(3,4-dimethoxyphenyl)ethyl]-2-(methoxy-imino)acetamide of the formula




embedded image


  • (18-2) N-[2-(3,4-dimethoxyphenyl)ethyl]-2-(methoxyimino)-2-(5,6,7,8-tetrahydronaphthalen-2-yl)acetamide of the formula





embedded image


  • (18-3) 2-(4-chlorophenyl)-N-[2-(3,4-dimethoxyphenyl)ethyl]-2-(methoxyimino)acetamide of the formula





embedded image


  • (18-4) 2-(4-bromophenyl)-N-[2-(3,4-dimethoxyphenyl)ethyl]-2-(methoxyimino)acetamide of the formula





embedded image


  • (18-5) 2-(4-methylphenyl)-N-[2-(3,4-dimethoxyphenyl)ethyl]-2-(methoxyimino)acetamide of the formula





embedded image


  • (18-6) 2-(4-ethylphenyl)-N-[2-(3,4-dimethoxyphenyl)ethyl]-2-(methoxyimino)acetamide of the formula





embedded image


Preferred mixing partners of group (19) are

  • (19-1) acibenzolar-S-methyl (known from EP-A 0 313 512) of the formula




embedded image


  • (19-2) chlorothalonil (known from U.S. Pat. No. 3,290,353) of the formula





embedded image


  • (19-3) cymoxanil (known from DE-A 23 12 956) of the formula





embedded image


  • (19-4) edifenphos (known from DE-A 14 93 736) of the formula





embedded image


  • (19-5) famoxadone (known from EP-A 0 393 911) of the formula





embedded image


  • (19-6) fluazinam (known from EP-A 0 031 257) of the formula





embedded image


  • (19-7) copper oxychloride

  • (19-9) oxadixyl (known from DE-A 30 30 026) of the formula





embedded image


  • (19-10) spiroxamine (known from DE-A 37 35 555) of the formula





embedded image


  • (19-11) dithianon (known from JP-A 44-29464) of the formula





embedded image


  • (19-12) metrafenone (known from EP-A 0 897 904) of the formula





embedded image


  • (19-13) fenamidone (known from EP-A 0 629 616) of the formula





embedded image


  • (19-14) 2,3-dibutyl-6-chlorothieno[2,3-d]pyrimidin-4(3H)one (known from WO 99/14202) of the formula





embedded image


  • (19-15) probenazole (known from U.S. Pat. No. 3,629,428) of the formula





embedded image


  • (19-16) isoprothiolane (known from U.S. Pat. No. 3,856,814) of the formula





embedded image


  • (19-17) kasugamycin (known from GB 1 094 567) of the formula





embedded image


  • (19-18) phthalide (known from JP-A 57-55844) of the formula





embedded image


  • (19-19) ferimzone (known from EP-A 0 019 450) of the formula





embedded image


  • (19-20) tricyclazole (known from DE-A 22 50 077) of the formula





embedded image


  • (19-21) N-({4-[(cyclopropylamino)carbonyl]phenyl}sulphonyl)-2-methoxybenzamide of the formula





embedded image


  • (19-22) 2-(4-chlorophenyl)-N-{2-[3-methoxy-4-(prop-2-yn-1-yloxy)phenyl]ethyl}-2-(prop-2-yn-1-yloxy)acetamide (known from WO 01/87822) of the formula





embedded image


Preferred mixing partners of group (20) are

  • (20-1) pencycuron (known from DE-A 27 32 257) of the formula




embedded image


  • (20-2) thiophanate-methyl (known from DE-A 18 06 123) of the formula





embedded image


  • (20-3) thiophanate-ethyl (known from DE-A 18 06 123) of the formula





embedded image


Preferred mixing partners of group (21) are

  • (21-1) fenoxanil (known from EP-A 0 262 393) of the formula




embedded image


  • (21-2) diclocymet (known from JP-A 7-206608) of the formula





embedded image


Preferred mixing partners of group (22) are

  • (22-1) 5-chloro-N-[(1S)-2,2,2-trifluoro-1-methylethyl]-6-(2,4,6-trifluorophenyl)[1,2,4]triazolo-[1,5-a]pyrimidine-7-amine (known from U.S. Pat. No. 5,986,135) of the formula




embedded image


  • (22-2) 5-chloro-N-[(1R)-1,2-dimethylpropyl]-6-(2,4,6-trifluorophenyl)[1,2,4]triazolo[1,5-a]-pyrimidine-7-amine (known from WO 02/38565) of the formula





embedded image


  • (22-3) 5-chloro-6-(2-chloro-6-fluorophenyl)-7-(4-methylpiperidin-1-yl)[1,2,4]triazolo[1,5-a]-pyrimidine (known from U.S. Pat. No. 5,593,996) of the formula





embedded image


  • (22-4) 5-chloro-6-(2,4,6-trifluorophenyl)-7-(4-methylpiperidin-1-yl)[1,2,4]triazolo[1,5-a]pyrimidine (known from DE-A 101 24 208) of the formula





embedded image


Preferred mixing partners of group (23) are

  • (23-1) 2-butoxy-6-iodo-3-propylbenzopyran-4-one (known from WO 03/014103) of the formula




embedded image


  • (23-2) 2-ethoxy-6-iodo-3-propylbenzopyran-4-one (known from WO 03/014103) of the formula





embedded image


  • (23-3) 6-iodo-2-propoxy-3-propylbenzopyran-4-one (known from WO 03/014103) of the formula





embedded image


  • (23-4) 2-but-2-ynyloxy-6-iodo-3-propylbenzopyran-4-one (known from WO 03/014103) of the formula





embedded image


  • (23-5) 6-iodo-2-(1-methylbutoxy)-3-propylbenzopyran-4-one (known from WO 03/014103) of the formula





embedded image


  • (23-6) 2-but-3-enyloxy-6-iodobenzopyran-4-one (known from WO 03/014103) of the formula





embedded image


  • (23-7) 3-butyl-6-iodo-2-isopropoxybenzopyran-4-one (known from WO 03/014103) of the formula





embedded image


Compound (6-7), carpropamid, has three asymmetrically substituted carbon atoms. Accordingly, compound (6-7) can be present as a mixture of different isomers or else in the form of a single component. Particular preference is given to the compounds

  • (1S,3R)-2,2-dichloro-N-[(1R)-1-(4-chlorophenyl)ethyl]-1-ethyl-3-methylcyclopropanecarboxamide of the formula




embedded image


  • (1R,3S)-2,2-dichloro-N-[(1R)-1-(4-chlorophenyl)ethyl]-1-ethyl-3-methylcyclopropanecarboxamide of the formula





embedded image


Particularly preferred mixing partners are the following active compounds:

  • (2-1) azoxystrobin
  • (2-2) fluoxastrobin
  • (2-3) (2E)-2-(2-{[6-(3-chloro-2-methylphenoxy)-5-fluoro-4-pyrimidinyl]oxy}phenyl)-2-(methoxyimino)-N-methylethanamide
  • (2-4) trifloxystrobin
  • (2-5) (2E)-2-(methoxyimino)-N-methyl-2-(2-{[({(1E)-1-[3-(trifluoromethyl)-phenyl]ethylidene}amino)oxy]methyl}phenyl)ethanamide
  • (2-6) (2E)-2-(methoxyimino)-N-methyl-2-{2-[(E)-({1-[3-(trifluoromethyl)phenyl]-ethoxy}imino)methyl]phenyl}ethanamide
  • (2-8) 5-methoxy-2-methyl-4-(2-{[({(1E)-1-[3-(trifluoromethyl)phenyl]ethylidene}-amino)oxy]methyl}phenyl)-2,4-dihydro-3H-1,2,4-triazol-3-one
  • (2-11) picoxystrobin
  • (2-9) kresoxim-methyl
  • (2-10) dimoxystrobin
  • (2-12) pyraclostrobin
  • (2-13) metominostrobin
  • (3-3) propiconazole
  • (3-4) difenoconazole
  • (3-6) cyproconazole
  • (3-7) hexaconazole
  • (3-8) penconazole
  • (3-9) myclobutanil
  • (3-10) tetraconazole
  • (3-13) flusilazole
  • (3-15) prothioconazole
  • (3-16) fenbuconazole
  • (3-17) tebuconazole
  • (3-21) bitertanol
  • (3-22) triadimenol
  • (3-23) triadimefon
  • (3-12) epoxiconazole
  • (3-19) metconazole
  • (3-24) fluquinconazole
  • (4-1) dichlofluanid
  • (4-2) tolylfluanid
  • (5-1) iprovalicarb
  • (5-3) benthiavalicarb
  • (6-2) boscalid
  • (6-5) ethaboxam
  • (6-6) fenhexamid
  • (6-7) carpropamid
  • (6-8) 2-chloro-4-[(2-fluoro-2-methylpropanoyl)amino]-N,N-dimethylbenzamide
  • (6-9) picobenzamid
  • (6-10) zoxamide
  • (6-11) 3,4-dichloro-N-(2-cyanophenyl)isothiazole-5-carboxamide
  • (6-14) penthiopyrad
  • (6-16) N-[2-(1,3-dimethylbutyl)phenyl]-1-methyl-4-(trifluoromethyl)-1H-pyrrole-3-carboxamide
  • (7-1) mancozeb
  • (7-2) maneb
  • (7-4) propineb
  • (7-5) thiram
  • (7-6) zineb
  • (8-1) benalaxyl
  • (8-2) furalaxyl
  • (8-3) metalaxyl
  • (8-4) metalaxyl-M
  • (8-5) benalaxyl-M
  • (9-1) cyprodinil
  • (9-2) mepanipyrim
  • (9-3) pyrimethanil
  • (10-1) 6-chloro-5-[(3,5-dimethylisoxazol-4-yl)sulphonyl]-2,2-difluoro-5H-[1,3]dioxolo[4,5-f]-benzimidazole
  • (10-3) carbendazim
  • (11-1) diethofencarb
  • (11-2) propamocarb
  • (11-3) propamocarb-hydrochloride
  • (11-4) propamocarb-fosetyl
  • (12-2) captan
  • (12-3) folpet
  • (12-4) iprodione
  • (12-5) procymidone
  • (13-1) dodine
  • (13-2) guazatine
  • (13-3) iminoctadine triacetate
  • (14-1) cyazofamid
  • (14-2) prochloraz
  • (14-3) triazoxide
  • (15-5) dimethomorph
  • (15-4) fenpropimorph
  • (16-2) fludioxonil
  • (17-1) fosetyl-Al
  • (17-2) phosphonic acid
  • (19-1) acibenzolar-S-methyl
  • (19-2) chlorothalonil
  • (19-3) cymoxanil
  • (19-5) famoxadone
  • (19-7) copper oxychloride
  • (19-6) fluazinam
  • (19-9) oxadixyl
  • (19-10) spiroxamine
  • (19-13) fenamidone
  • (19-22) 2-(4-chlorophenyl)-N-{2-[3-methoxy-4-(prop-2-yn-1-yloxy)phenyl]ethyl}-2-(prop-2-yn-1-yloxy)acetamide
  • (20-1) pencycuron
  • (20-2) thiophanate-methyl
  • (22-1) 5-chloro-N-[(1S)-2,2,2-trifluoro-1-methylethyl]-6-(2,4,6-trifluorophenyl)[1,2,4]-triazolo[1,5-a]pyrimidine-7-amine
  • (22-2) 5-chloro-N-[(1R)-1,2-dimethylpropyl]-6-(2,4,6-trifluorophenyl)[1,2,4]triazolo[1,5-a]-pyrimidine-7-amine
  • (22-4) 5-chloro-6-(2,4,6-trifluorophenyl)-7-(4-methylpiperidin-1-yl)[1,2,4]triazolo[1,5-a]pyrimidine
  • (23-1) 2-butoxy-6-iodo-3-propylbenzopyran-4-one
  • (23-2) 2-ethoxy-6-iodo-3-propylbenzopyran-4-one
  • (23-3) 6-iodo-2-propoxy-3-propylbenzopyran-4-one


Very particularly preferred mixing partners are the following active compounds:

  • (2-2) fluoxastrobin
  • (2-3) (2E)-2-(2-{[6-(3-chloro-2-methylphenoxy)-5-fluoro-4-pyrimidinyl]oxy}phenyl)-2-(methoxyimino)-N-methylethanamide
  • (2-4) trifloxystrobin
  • (3-15) prothioconazole
  • (3-17) tebuconazole
  • (3-21) bitertanol
  • (3-22) triadimenol
  • (3-24) fluquinconazole
  • (4-1) dichlofluanid
  • (4-2) tolylfluanid
  • (5-1) iprovalicarb
  • (6-6) fenhexamid
  • (6-7) carpropamid
  • (6-9) picobenzamid
  • (6-14) penthiopyrad
  • (7-4) propineb
  • (8-4) metalaxyl-M
  • (8-5) benalaxyl-M
  • (9-3) pyrimethanil
  • (10-3) carbendazim
  • (11-4) propamocarb-fosetyl
  • (12-4) iprodione
  • (14-2) prochloraz
  • (14-3) triazoxide
  • (16-2) fludioxonil
  • (19-10) spiroxamine
  • (19-22) 2-(4-chlorophenyl)-N-{2-[3-methoxy-4-(prop-2-yn-1-yloxy)phenyl]ethyl}-2-(prop-2-yn-1-yloxy)acetamide
  • (22-4) 5-chloro-6-(2,4,6-trifluorophenyl)-7-(4-methylpiperidin-1-yl)[1,2,4]triazolo[1,5-a]pyrimidine


Preferred active compound combinations consisting of two groups of active compounds and comprising in each case at least one carboxamide of the formula (I) (group 1) and at least one active compound from the stated group (2) to (23) are described below. These combinations are the active compound combinations A to T.


Among the preferred active compound combinations A to T, emphasis is given to those comprising a carboxamide of the formula (I) (group 1)




embedded image



in which R1, R2, R3 and A are as defined above.


Particular preference is given to active compound combinations A to T comprising a carboxamide of the formula (I) (group 1)




embedded image



in which

  • R1 represents hydrogen or fluorine,
  • R2 represents fluorine, chlorine, bromine, trifluoromethyl or represents —CH═N—OCH3,
  • R3 represents hydrogen, fluorine or chlorine,
  • A represents one of the radicals A1 or A2 below:




embedded image


  • R6 represents methyl,

  • R7 represents methyl, difluoromethyl or trifluoromethyl,

  • R8 represents hydrogen or fluorine,

  • R9 represents methyl,

  • R10 represents methyl, difluoromethyl or trifluoromethyl.



Very particular preference is given to active compound combinations A to T in which the carboxamide of the formula (I) (group 1) is selected from the list below:

  • (1-1) N-(3′,4′-dichloro-5-fluoro-1,1′-biphenyl-2-yl)-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide
  • (1-2) 3-(difluoromethyl)-N-{3′-fluoro-4′-[(E)-(methoxyimino)methyl]-1,1′-biphenyl-2-yl}-1-methyl-1H-pyrazole-4-carboxamide
  • (1-3) 3-(trifluoromethyl)-N-{3′-fluoro-4′-[(E)-(methoxyimino)methyl]-1,1′-biphenyl-2-yl}-1-methyl-1H-pyrazole-4-carboxamide
  • (1-4) N-(3′,4′-dichloro-1,1′-biphenyl-2-yl)-5-fluoro-1,3-dimethyl-1H-pyrazole-4-carboxamide
  • (1-5) N-(4′-chloro-3′-fluoro-1,1′-biphenyl-2-yl)-2-methyl-4-(trifluoromethyl)-1,3-thiazole-5-carboxamide
  • (1-6) N-(4′-chloro-1,1′-biphenyl-2-yl)-4-(difluoromethyl)-2-methyl-1,3-thiazole-5-carboxamide
  • (1-7) N-(4′-bromo-1,1′-biphenyl-2-yl)-4-(difluoromethyl)-2-methyl-1,3-thiazole-5-carboxamide
  • (1-8) 4-(difluoromethyl)-2-methyl-N-[4′-(trifluoromethyl)-1,1′-biphenyl-2-yl]-1,3-thiazole-5-carboxamide
  • (1-9) N-(4′-chloro-3′-fluoro-1,1′-biphenyl-2-yl)-4-(difluoromethyl)-2-methyl-1,3-thiazole-5-carboxamide


Especially preferred are active compound combinations A to T in which the carboxamide of the formula (I) (group 1) is selected from the list below:

  • (1-1) N-(3′,4′-dichloro-5-fluoro-1,1′-biphenyl-2-yl)-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide
  • (1-7) N-(4′-bromo-1,1′-biphenyl-2-yl)-4-(difluoromethyl)-2-methyl-1,3-thiazole-5-carboxamide
  • (1-8) 4-(difluoromethyl)-2-methyl-N-[4′-(trifluoromethyl)-1,1′-biphenyl-2-yl]-1,3-thiazole-5-carboxamide
  • (1-9) N-(4′-chloro-3′-fluoro-1,1′-biphenyl-2-yl)-4-(difluoromethyl)-2-methyl-1,3-thiazole-5-carboxamide.


In addition to a carboxamide of the formula (I) (group 1), the active compound combinations A also comprise a strobilurin of the formula (II) (group 2)




embedded image



in which A1, L and R14 are as defined above.


Particular preference is given to active compound combinations A in which the strobilurin of the formula (II) (group 2) is selected from the list below:

  • (2-1) azoxystrobin
  • (2-2) fluoxastrobin
  • (2-3) (2E)-2-(2-{[6-(3-chloro-2-methylphenoxy)-5-fluoro-4-pyrimidinyl]oxy}phenyl)-2-(methoxyimino)-N-methylethanamide
  • (2-4) trifloxystrobin
  • (2-5) (2E)-2-(methoxyimino)-N-methyl-2-(2-{[({(1E)-1-[3-(trifluoromethyl)phenyl]ethylidene}-amino)oxy]methyl}phenyl)ethanamide
  • (2-6) (2E)-2-(methoxyimino)-N-methyl-2-{2-[(E)-({1-[3-(trifluoromethyl)phenyl]ethoxy}imino)-methyl]phenyl}ethanamide
  • (2-7) orysastrobin
  • (2-8) 5-methoxy-2-methyl-4-(2-{[({(1E)-1-[3-(trifluoromethyl)phenyl]ethylidene}amino)oxy]-methyl}phenyl)-2,4-dihydro-3H-1,2,4-triazol-3-one
  • (2-9) kresoxim-methyl
  • (2-10) dimoxystrobin
  • (2-11) picoxystrobin
  • (2-12) pyraclostrobin
  • (2-13) metominostrobin


Very particular preference is given to active compound combinations A in which the strobilurin of the formula (II) (group 2) is selected from the list below:

  • (2-1) azoxystrobin
  • (2-2) fluoxastrobin
  • (2-3) (2E)-2-(2-{[6-(3-chloro-2-methylphenoxy)-5-fluoro-4-pyrimidinyl]oxy}phenyl)-2-(methoxyimino)-N-methylethanamide
  • (2-4) trifloxystrobin
  • (2-12) pyraclostrobin
  • (2-9) kresoxim-methyl
  • (2-10) dimoxystrobin
  • (2-11) picoxystrobin
  • (2-13) metominostrobin


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 (I)
Strobilurin of the formula (II)





A-1
(1-1) N-(3′,4′-dichloro-5-fluoro-1,1′-biphenyl-2-yl)-3-
(2-1) azoxystrobin



(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide



A-2
(1-1) N-(3′,4′-dichloro-5-fluoro-1,1′-biphenyl-2-yl)-3-
(2-2) fluoxastrobin



(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide



A-3
(1-1) N-(3′,4′-dichloro-5-fluoro-1,1′-biphenyl-2-yl)-
(2-3) (2E)-2-(2-{[6-(3-chloro-2-



3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide
methylphenoxy)-5-fluoro-4-




pyrimidinyl]oxy}phenyl)-2-




(methoxyimino)-N-methylethanamide


A-4
(1-1) N-(3′,4′-dichloro-5-fluoro-1,1′-biphenyl-2-yl)-3-
(2-4) trifloxystrobin



(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide



A-5
(1-1) N-(3′,4′-dichloro-5-fluoro-1,1′-biphenyl-2-yl)-3-
(2-12) pyraclostrobin



(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide



A-6
(1-2) 3-(difluoromethyl)-N-{3′-fluoro-4′-[(E)-
(2-1) azoxystrobin



(methoxyimino)methyl]-1,1′-biphenyl-2-yl}-1-methyl-




1H-pyrazole-4-carboxamide



A-7
(1-2) 3-(difluoromethyl)-N-{3′-fluoro-4′-[(E)-
(2-2) fluoxastrobin



(methoxyimino)methyl]-1,1′-biphenyl-2-yl}-1-methyl-




1H-pyrazole-4-carboxamide



A-8
(1-2) 3-(difluoromethyl)-N-{3′-fluoro-4′-[(E)-
(2-3) (2E)-2-(2-{[6-(3-chloro-2-



(methoxyimino)methyl]-1,1′-biphenyl-2-yl}-1-methyl-
methylphenoxy)-5-fluoro-4-



1H-pyrazole-4-carboxamide
pyrimidinyl]oxy}phenyl)-2-




(methoxyimino)-N-methylethanamide


A-9
(1-2) 3-(difluoromethyl)-N-{3′-fluoro-4′-[(E)-
(2-4) trifloxystrobin



(methoxyimino)methyl]-1,1′-biphenyl-2-yl}-1-methyl-




1H-pyrazole-4-carboxamide



A-10
(1-2) 3-(difluoromethyl)-N-{3′-fluoro-4′-[(E)-
(2-12) pyraclostrobin



(methoxyimino)methyl]-1,1′-biphenyl-2-yl}-1-methyl-




1H-pyrazole-4-carboxamide



A-11
(1-3) 3-(trifluoromethyl)-N-{3′-fluoro-4′-[(E)-
(2-1) azoxystrobin



(methoxyimino)methyl]-1,1′-biphenyl-2-yl}-1-methyl-




1H-pyrazole-4-carboxamide



A-12
(1-3) 3-(trifluoromethyl)-N-{3′-fluoro-4′-[(E)-
(2-2) fluoxastrobin



(methoxyimino)methyl]-1,1′-biphenyl-2-yl}-1-methyl-




1H-pyrazole-4-carboxamide



A-13
(1-3) 3-(trifluoromethyl)-N-{3′-fluoro-4′-[(E)-
(2-3) (2E)-2-(2-{[6-(3-chloro-2-



(methoxyimino)methyl]-1,1′-biphenyl-2-yl}-methyl-
methylphenoxy)-5-fluoro-4-



1H-pyrazole-4-carboxamide
pyrimidinyl]oxy}phenyl)-2-




(methoxyimino)-N-methylethanamide


A-14
(1-3) 3-(trifluoromethyl)-N-{3′-fluoro-4′-[(E)-
(2-4) trifloxystrobin



(methoxyimino)methyl]-1,1′-biphenyl-2-yl}-methyl-




1H-pyrazole-4-carboxamide



A-15
(1-3) 3-(trifluoromethyl)-N-{3′-fluoro-4′-[(E)-
(2-12) pyraclostrobin



(methoxyimino)methyl]-1,1′-biphenyl-2-yl}-methyl-




1H-pyrazole-4-carboxamide



A-16
(1-4) N-(3′,4′-dichloro-1,1′-biphenyl-2-yl)-5-fluoro-
(2-1) azoxystrobin



1,3-dimethyl-1H-pyrazole-4-carboxamide



A-17
(1-4) N-(3′,4′-dichloro-1,1′-biphenyl-2-yl)-5-fluoro-
(2-2) fluoxastrobin



1,3-dimethyl-1H-pyrazole-4-carboxamide



A-18
(1-4) N-(3′,4′-dichloro-1,1′-biphenyl-2-yl)-5-fluoro-
(2-3) (2E)-2-(2-{[6-(3-chloro-2-



1,3-dimethyl-1H-pyrazole-4-carboxamide
methylphenoxy)-5-fluoro-4-




pyrimidinyl]oxy}phenyl)-2-




(methoxyimino)-N-methylethanamide


A-19
(1-4) N-(3′,4′-dichloro-1,1′-biphenyl-2-yl)-5-fluoro-
(2-4) trifloxystrobin



1,3-dimethyl-1H-pyrazole-4-carboxamide



A-20
(1-4) N-(3′,4′-dichloro-1,1′-biphenyl-2-yl)-5-fluoro-
(2-12) pyraclostrobin



1,3-dimethyl-1H-pyrazole-4-carboxamide



A-21
(1-5) N-(4′-chloro-3′-fluoro-1,1′-biphenyl-2-yl)-2-methyl-
(2-1) azoxystrobin



4-(trifluoromethyl)-1,3-thiazole-5-carboxamide



A-22
(1-5) N-(4′-chloro-3′-fluoro-1,1′-biphenyl-2-yl)-2-methyl-
(2-2) fluoxastrobin



4-(trifluoromethyl)-1,3-thiazole-5-carboxamide



A-23
(1-5) N-(4′-chloro-3′-fluoro-1,1′-biphenyl-2-yl)-2-methyl-
(2-3) (2E)-2-(2-{[6-(3-chloro-2-



4-(trifluoromethyl)-1,3-thiazole-5-carboxamide
methylphenoxy)-5-fluoro-4-




pyrimidinyl]oxy}phenyl)-2-




(methoxyimino)-N-methylethanamide


A-24
(1-5) N-(4′-chloro-3′-fluoro-1,1′-biphenyl-2-yl)-2-methyl-
(2-4) trifloxystrobin



4-(trifluoromethyl)-1,3-thiazole-5-carboxamide



A-25
(1-5) N-(4′-chloro-3′-fluoro-1,1′-biphenyl-2-yl)-2-methyl-
(2-12) pyraclostrobin



4-(trifluoromethyl)-1,3-thiazole-5-carboxamide



A-26
(1-6) N-(4′-chloro-1,1′-biphenyl-2-yl)-4-(difluoromethyl)-
(2-1) azoxystrobin



2-methyl-1,3-thiazole-5-carboxamide



A-27
(1-6) N-(4′-chloro-1,1′-biphenyl-2-yl)-4-(difluoromethyl)-
(2-2) fluoxastrobin



2-methyl-1,3-thiazole-5-carboxamide



A-28
(1-6) N-(4′-chloro-1,1′-biphenyl-2-yl)-4-(difluoro-methyl)-
(2-3) (2E)-2-(2-{[6-(3-chloro-2-



2-methyl-1,3-thiazole-5-carboxamide
methylphenoxy)-5-fluoro-4-




pyrimidinyl]oxy}phenyl)-2-




o(methxyimino)-N-methylethanamide


A-29
(1-6) N-(4′-chloro-1,1′-biphenyl-2-yl)-4-(difluoromethyl)-
(2-4) trifloxystrobin



2-methyl-1,3-thiazole-5-carboxamide



A-30
(1-6) N-(4′-chloro-1,1′-biphenyl-2-yl)-4-(difluoromethyl)-
(2-12) pyraclostrobin



2-methyl-1,3-thiazole-5-carboxamide



A-31
(1-7) N-(4′-bromo-1,1′-biphenyl-2-yl)-4-(difluoromethyl)-
(2-1) azoxystrobin



2-methyl-1,3-thiazole-5-carboxamide



A-32
(1-7) N-(4′-bromo-1,1′-biphenyl-2-yl)-4-(difluoromethyl)-
(2-2) fluoxastrobin



2-methyl-1,3-thiazole-5-carboxamide



A-33
(1-7) N-(4′-bromo-1,1′-biphenyl-2-yl)-4-(difluoromethyl)-
(2-3) (2E)-2-(2-{[6-(3-chloro-2-



2-methyl-1,3-thiazole-5-carboxamide
methylphenoxy)-5-fluoro-4-




pyrimidinyl]oxy}phenyl)-2-




(methoxyimino)-N-methylethanamide


A-34
(1-7) N-(4′-bromo-1,1′-biphenyl-2-yl)-4-(difluoromethyl)-
(2-4) trifloxystrobin



2-methyl-1,3-thiazole-5-carboxamide



A-35
(1-7) N-(4′-bromo-1,1′-biphenyl-2-yl)-4-(difluoromethyl)-
(2-12) pyraclostrobin



2-methyl-1,3-thiazole-5-carboxamide



A-36
(1-8) 4-(difluoromethyl)-2-methyl-N-[4′-(trifluoromethyl)-
(2-1) azoxystrobin



1,1′-biphenyl-2-yl]-1,3-thiazole-5-carboxamide



A-37
(1-8) 4-(difluoromethyl)-2-methyl-N-[4′-(trifluoromethyl)-
(2-2) fluoxastrobin



1,1′-biphenyl-2-yl]-1,3-thiazole-5-carboxamide



A-38
(1-8) 4-(difluoromethyl)-2-methyl-N-[4′-(trifluoromethyl)-
(2-3) (2E)-2-(2-{[6-(3-chloro-2-



1,1′-biphenyl-2-yl]-1,3-thiazole-5-carboxamide
methylphenoxy)-5-fluoro-4-




pyrimidinyl]oxy}phenyl)-2-




(methoxyimino)-N-methylethanamide


A-39
(1-8) 4-(difluoromethyl)-2-methyl-N-[4′-(trifluoromethyl)-
(2-4) trifloxystrobin



1,1′-biphenyl-2-yl]-1,3-thiazole-5-carboxamide



A-40
(1-8) 4-(difluoromethyl)-2-methyl-N-[4′-(trifluoromethyl)-
(2-12) pyraclostrobin



1,1′-biphenyl-2-yl]-1,3-thiazole-5-carboxamide



A-41
(1-1) N-(3′,4′-dichloro-5-fluoro-1,1′-biphenyl-2-yl)-3-
(2-9) kresoxim-methyl



(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide



A-42
(1-1) N-(3′,4′-dichloro-5-fluoro-1,1′-biphenyl-2-yl)-3-
(2-10) dimoxystrobin



(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide



A-43
(1-1) N-(3′,4′-dichloro-5-fluoro-1,1′-biphenyl-2-yl)-3-
(2-11) picoxystrobin



(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide



A-44
(1-1) N-(3′,4′-dichloro-5-fluoro-1,1′-biphenyl-2-yl)-3-
(2-13) metominostrobin



(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide



A-45
(1-7) N-(4′-bromo-1,1′-biphenyl-2-yl)-4-(difluoromethyl)-
(2-9) kresoxim-methyl



2-methyl-1,3-thiazole-5-carboxamide



A-46
(1-7) N-(4′-bromo-1,1′-biphenyl-2-yl)-4-(difluoromethyl)-
(2-10) dimoxystrobin



2-methyl-1,3-thiazole-5-carboxamide



A-47
(1-7) N-(4′-bromo-1,1′-biphenyl-2-yl)-4-(difluoromethyl)-
(2-11) picoxystrobin



2-methyl-1,3-thiazole-5-carboxamide



A-48
(1-7) N-(4′-bromo-1,1′-biphenyl-2-yl)-4-(difluoromethyl)-
(2-13) metominostrobin



2-methyl-1,3-thiazole-5-carboxamide



A-49
(1-8) 4-(difluoromethyl)-2-methyl-N-[4′-(trifluoromethyl)-
(2-9) kresoxim-methyl



1,1′-biphenyl-2-yl]-1,3-thiazole-5-carboxamide



A-50
(1-8) 4-(difluoromethyl)-2-methyl-N-[4′-(trifluoromethyl)-
(2-10) dimoxystrobin



1,1′-biphenyl-2-yl]-1,3-thiazole-5-carboxamide



A-51
(1-8) 4-(difluoromethyl)-2-methyl-N-[4′-(trifluoromethyl)-
(2-11) picoxystrobin



1,1′-biphenyl-2-yl]-1,3-thiazole-5-carboxamide



A-52
(1-8) 4-(difluoromethyl)-2-methyl-N-[4′-(trifluoromethyl)-
(2-13) metominostrobin



1,1′-biphenyl-2-yl]-1,3-thiazole-5-carboxamide



A-53
(1-9) N-(4′-chloro-3′-fluoro-1,1′-biphenyl-2-yl)-4-
(2-9) kresoxim-methyl



(difluoromethyl)-2-methyl-1,3-thiazole-5-carboxamide



A-54
(1-9) N-(4′-chloro-3′-fluoro-1,1′-biphenyl-2-yl)-4-
(2-10) dimoxystrobin



(difluoromethyl)-2-methyl-1,3-thiazole-5-carboxamide



A-55
(1-9) N-(4′-chloro-3′-fluoro-1,1′-biphenyl-2-yl)-4-
(2-11) picoxystrobin



(difluoromethyl)-2-methyl-1,3-thiazole-5-carboxamide



A-56
(1-9) N-(4′-chloro-3′-fluoro-1,1′-biphenyl-2-yl)-4-
(2-13) metominostrobin



(difluoromethyl)-2-methyl-1,3-thiazole-5-carboxamide



A-57
(1-9) N-(4′-chloro-3′-fluoro-1,1′-biphenyl-2-yl)-4-
(2-1) azoxystrobin



(difluoromethyl)-2-methyl-1,3-thiazole-5-carboxamide



A-58
(1-9) N-(4′-chloro-3′-fluoro-1,1′-biphenyl-2-yl)-4-
(2-2) fluoxastrobin



(difluoromethyl)-2-methyl-1,3-thiazole-5-carboxamide



A-59
(1-9) N-(4′-chloro-3′-fluoro-1,1′-biphenyl-2-yl)-4-
(2-3) (2E)-2-(2-{[6-(3-chloro-2-



(difluoromethyl)-2-methyl-1,3-thiazole-5-carboxamide
methylphenoxy)-5-fluoro-4-




pyrimidinyl]oxy{phenyl)-2-




(methoxyimino)-N-methylethanamide


A-60
(1-9) N-(4′-chloro-3′-fluoro-1,1′-biphenyl-2-yl)-4-
(2-4) trifloxystrobin



(difluoromethyl)-2-methyl-1,3-thiazole-5-carboxamide



A-61
(1-9) N-(4′-chloro-3′-fluoro-1,1′-biphenyl-2-yl)-4-
(2-12) pyraclostrobin



(difluoromethyl)-2-methyl-1,3-thiazole-5-carboxamide









In addition to a carboxamide of the formula (I) (group 1), the active compound combinations B also comprise a triazole of the formula (III) (group 3)




embedded image



in which Q, m, R16, R17, A4, A5, R18 and R19 are as defined above.


Preference is given to active compound combinations B in which the triazole of the formula (III) (group 3) is selected from the list below:

  • (3-1) azaconazole
  • (3-2) etaconazole
  • (3-3) propiconazole
  • (3-4) difenoconazole
  • (3-5) bromuconazole
  • (3-6) cyproconazole
  • (3-7) hexaconazole
  • (3-8) penconazole
  • (3-9) myclobutanil
  • (3-10) tetraconazole
  • (3-11) flutriafol
  • (3-12) epoxiconazole
  • (3-13) flusilazole
  • (3-14) simeconazole
  • (3-15) prothioconazole
  • (3-16) fenbuconazole
  • (3-17) tebuconazole
  • (3-18) ipconazole
  • (3-19) metconazole
  • (3-20) triticonazole
  • (3-21) bitertanol
  • (3-22) triadimenol
  • (3-23) triadimefon
  • (3-24) fluquinconazole
  • (3-25) quinconazole


Particular preference is given to active compound combinations B in which the triazole of the formula (III) (group 3) is selected from the list below:

  • (3-3) propiconazole
  • (3-4) difenoconazole
  • (3-6) cyproconazole
  • (3-7) hexaconazole
  • (3-15) prothioconazole
  • (3-17) tebuconazole
  • (3-21) bitertanol
  • (3-19) metconazole
  • (3-22) triadimenol
  • (3-24) fluquinconazole


Emphasis is given to the active compound combinations B listed in Table 2 below:









TABLE 2







Active compound combinations B











Triazole of the


No.
Carboxamide of the formula (I)
formula (III)





B-1
(1-1) N-(3′,4′-dichloro-5-fluoro-1,1′-biphenyl-2-yl)-3-
(3-3) propiconazole



(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide



B-2
(1-1) N-(3′,4′-dichloro-5-fluoro-1,1′-biphenyl-2-yl)-3-
(3-6) cyproconazole



(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide



B-3
(1-1) N-(3′,4′-dichloro-5-fluoro-1,1′-biphenyl-2-yl)-3-
(3-15) prothioconazole



(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide



B-4
(1-1) N-(3′,4′-dichloro-5-fluoro-1,1′-biphenyl-2-yl)-3-
(3-17) tebuconazole



(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide



B-5
(1-1) N-(3′,4′-dichloro-5-fluoro-1,1′-biphenyl-2-yl)-3-
(3-21) bitertanol



(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide



B-6
(1-2) 3-(difluoromethyl)-N-{3′-fluoro-4′-[(E)-(methoxyimino)-
(3-3) propiconazole



methyl]-1,1′-biphenyl-2-yl}-1-methyl-1H-pyrazole-4-




carboxamide



B-7
(1-2) 3-(difluoromethyl)-N-{3′-fluoro-4′-[(E)-(methoxyimino)-
(3-6) cyproconazole



methyl]-1,1′-biphenyl-2-yl}-1-methyl-1H-pyrazole-4-




carboxamide



B-8
(1-2) 3-(difluoromethyl)-N-{3′-fluoro-4′-[(E)-(methoxyimino)-
(3-15) prothioconazole



methyl]-1,1′-biphenyl-2-yl}-1-methyl-1H-pyrazole-4-




carboxamide



B-9
(1-2) 3-(difluoromethyl)-N-{3′-fluoro-4′-[(E)-(methoxyimino)-
(3-17) tebuconazole



methyl]-1,1′-bipheny1-2-yl}-1-methyl-1H-pyrazole-4-




carboxamide



B- 10
(1-2) 3-(difluoromethyl)-N-{3′-fluoro-4′-[(E)-(methoxyimino)-
(3-21) bitertanol



methyl]-1,1′-biphenyl-2-yl}-1-methyl-1H-pyrazole-4-




carboxamide



B- 11
(1-3) 3-(trifluoromethyl)-N-{3′-fluoro-4′-[(E)-(methoxyimino)-
(3-3) propiconazole



methyl]-1,1′-biphenyl-2-yl}-1-methyl-1H-pyrazole-4-




carboxamide



B- 12
(1-3) 3-(trifluoromethyl)-N-{3′-fluoro-4′-[(E)-(methoxyimino)-
(3-6) cyproconazole



methyl]-1,1′-biphenyl-2-yl}-1-methyl-1H-pyrazole-4-




carboxamide



B-13
(1-3) 3-(trifluoromethyl)-N-{3′-fluoro-4′-[(E)-(methoxyimino)-
(3-15) prothioconazole



methyl]-1,1′-biphenyl-2-yl}-1-methyl-1H-pyrazole-4-




carboxamide



B-14
(1-3) 3-(trifluoromethyl)-N-{3′-fluoro-4′-[(E)-(methoxyimino)-
(3-17) tebuconazole



methyl]-1,1′-biphenyl-2-yl}-1-methyl-1H-pyrazole-4-




carboxamide



B-15
(1-3) 3-(trifluoromethyl)-N-{3′-fluoro-4′-[(E)-(methoxyimino)-
(3-21) bitertanol



methyl]-1,1′-biphenyl-2-yl}-1-methyl-1H-pyrazole-4-




carboxamide



B-16
(1-4) N-(3′,4′-dichloro-1,1′-biphenyl-2-yl)-5-fluoro-1,3-
(3-3) propiconazole



dimethyl-1H-pyrazole-4-carboxamide



B-17
(1-4) N-(3′,4′-dichloro-1,1′-biphenyl-2-yl)-5-fluoro-1,3-
(3-6) cyproconazole



dimethyl-1H-pyrazole-4-carboxamide



B-18
(1-4) N-(3′,4′-dichloro-1,1′-biphenyl-2-yl)-5-fluoro-1,3-
(3-15) prothioconazole



dimethyl-1H-pyrazole-4-carboxamide



B-19
(1-4) N-(3′,4′-dichloro-1,1′-biphenyl-2-yl)-5-fluoro-1,3-
(3-17) tebuconazole



dimethyl-1H-pyrazole-4-carboxamide



B-20
(1-4) N-(3′,4′-dichloro-1,1′-biphenyl-2-yl)-5-fluoro-1,3-
(3-21) bitertanol



dimethyl-1H-pyrazole-4-carboxamide



B-21
(1-5) N-(4′-chloro-3′-fluoro-1,1′-biphenyl-2-yl)-2-methyl-
(3-3) propiconazole



4-(trifluoromethyl)-1,3-thiazole-5-carboxamide



B-22
(1-5) N-(4′-chloro-3′-fluoro-1,1′-biphenyl-2-yl)-2-methyl-
(3-6) cyproconazole



4-(trifluoromethyl)-1,3-thiazole-5-carboxamide



B-23
(1-5) N-(4′-chloro-3′-fluoro-1,1′-biphenyl-2-yl)-2-methyl-
(3-15) prothioconazole



4-(trifluoromethyl)-1,3-thiazole-5-carboxamide



B-24
(1-5) N-(4′-chloro-3′-fluoro-1,1′-biphenyl-2-yl)-2-methyl-
(3-17) tebuconazole



4-(trifluoromethyl)-1,3-thiazole-5-carboxamide



B-25
(1-5) N-(4′-chloro-3′-fluoro-1,1′-biphenyl-2-yl)-2-methyl-
(3-21) bitertanol



4-(trifluoromethyl)-1,3-thiazole-5-carboxamide



B-26
(1-6) N-(4′-chloro-1,1′-biphenyl-2-yl)-4-(difluoromethyl)-
(3-3) propiconazole



2-methyl-1,3-thiazole-5-carboxamide



B-27
(1-6) N-(4′-chloro-1,1′-biphenyl-2-yl)-4-(difluoromethyl)-
(3-6) cyproconazole



2-methyl-1,3-thiazole-5-carboxamide



B-28
(1-6) N-(4′-chloro-1,1′-biphenyl-2-yl)-4-(difluoromethyl)-
(3-15) prothioconazole



2-methyl-1,3-thiazole-5-carboxamide



B-29
(1-6) N-(4′-chloro-1,1′-biphenyl-2-yl)-4-(difluoromethyl)-
(3-17) tebuconazole



2-methyl-1,3-thiazole-5-carboxamide



B-30
(1-6) N-(4′-chloro-1,1′-biphenyl-2-yl)-4-(difluoromethyl)-
(3-21) bitertanol



2-methyl-1,3-thiazole-5-carboxamide



B-31
(1-7) N-(4′-bromo-1,1′-biphenyl-2-yl)-4-(difluoromethyl)-
(3-3) propiconazole



2-methyl-1,3-thiazole-5-carboxamide



B-32
(1-7) N-(4′-bromo-1,1′-biphenyl-2-yl)-4-(difluoromethyl)-
(3-6) cyproconazole



2-methyl-1,3-thiazole-5-carboxamide



B-33
(1-7) N-(4′-bromo-1,1′-biphenyl-2-yl)-4-(difluoromethyl)-
(3-15) prothioconazole



2-methyl-1,3-thiazole-5-carboxamide



B-34
(1-7) N-(4′-bromo-1,1′-biphenyl-2-yl)-4-(difluoromethyl)-
(3-17) tebuconazole



2-methyl-1,3-thiazole-5-carboxamide



B-35
(1-7) N-(4′-bromo-1,1′-biphenyl-2-yl)-4-(difluoromethyl)-
(3-21) bitertanol



2-methyl-1,3-thiazole-5-carboxamide



B-36
(1-8) 4-(difluoromethyl)-2-methyl-N-[4′-(trifluoromethyl)-1,1′-
(3-3) propiconazole



biphenyl-2-yl]-1,3-thiazole-5-carboxamide



B-37
(1-8) 4-(difluoromethyl)-2-methyl-N-[4′-(trifluoromethyl)-1,1′-
(3-6) cyproconazole



biphenyl-2-yl]-1,3-thiazole-5-carboxamide



B-38
(1-8) 4-(difluoromethyl)-2-methyl-N-[4′-(trifluoromethyl)-1,1′-
(3-15) prothioconazole



biphenyl-2-yl]-1,3-thiazole-5-carboxamide



B-39
(1-8) 4-(difluoromethyl)-2-methyl-N-[4′-(trifluoromethyl)-1,1′-
(3-17) tebuconazole



biphenyl-2-yl]-1,3-thiazole-5-carboxamide



B-40
(1-8) 4-(difluoromethyl)-2-methyl-N-[4′-(trifluoromethyl)-1,1′-
(3-21) bitertanol



biphenyl-2-yl]-1,3-thiazole-5-carboxamide



B-41
(1-1) N-(3′,4′-dichloro-5-fluoro-1,1′-biphenyl-2-yl)-3-
(3-4) difenoconazole



(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide



B-42
(1-1) N-(3′,4′-dichloro-5-fluoro-1,1′-biphenyl-2-yl)-3-
(3-7) hexaconazole



(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide



B-43
(1-1) N-(3′,4′-dichloro-5-fluoro-1,1′-biphenyl-2-yl)-3-
(3-19) metconazole



(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide



B-44
(1-1) N-(3′,4′-dichloro-5-fluoro-1,1′-biphenyl-2-yl)-3-
(3-22) triadimenol



(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide



B-45
(1-1) N-(3′,4′-dichloro-5-fluoro-1,1′-biphenyl-2-yl)-3-
(3-24) fluquinconazole



(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide



B-46
(1-7) N-(4′-bromo-1,1′-biphenyl-2-yl)-4-(difluoromethyl)-
(3-4) difenoconazole



2-methyl-1,3-thiazole-5-carboxamide



B-47
(1-7) N-(4′-bromo-1,1′-biphenyl-2-yl)-4-(difluoromethyl)-
(3-7) hexaconazole



2-methyl-1,3-thiazole-5-carboxamide



B-48
(1-7) N-(4′-bromo-1,1′-biphenyl-2-yl)-4-(difluoromethyl)-
(3-19) metconazole



2-methyl-1,3-thiazole-5-carboxamide



B-49
(1-7) N-(4′-bromo-1,1′-biphenyl-2-yl)-4-(difluoromethyl)-
(3-22) triadimenol



2-methyl-1,3-thiazole-5-carboxamide



B-50
(1-7) N-(4′-bromo-1,1′-biphenyl-2-yl)-4-(difluoromethyl)-
(3-24) fluquinconazole



2-methyl-1,3-thiazole-5-carboxamide



B-51
(1-8) 4-(difluoromethyl)-2-methyl-N-[4′-(trifluoromethyl)-1,1′-
(3-4) difenoconazole



biphenyl-2-yl]-1,3-thiazole-5-carboxamide



B-52
(1-8) 4-(difluoromethyl)-2-methyl-N-[4′-(trifluoromethyl)-1,1′-
(3-7) hexaconazole



biphenyl-2-yl]-1,3-thiazole-5-carboxamide



B-53
(1-8) 4-(difluoromethyl)-2-methyl-N-[4′-(trifluoromethyl)-1,1′-
(3-19) metconazole



biphenyl-2-yl]-1,3-thiazole-5-carboxamide



B-54
(1-8) 4-(difluoromethyl)-2-methyl-N-[4′-(trifluoromethyl)-1,1′-
(3-22) triadimenol



biphenyl-2-yl]-1,3-thiazole-5-carboxamide



B-55
(1-8) 4-(difluoromethyl)-2-methyl-N-[4′-(trifluoromethyl)-1,1′-
(3-24) fluquinconazole



biphenyl-2-yl]-1,3-thiazole-5-carboxamide



B-56
(1-9) N-(4′-chloro-3′-fluoro-1,1′-biphenyl-2-yl)-4-
(3-4) difenoconazole



(difluoromethyl)-2-methyl-1,3-thiazole-5-carboxamide



B-57
(1-9) N-(4′-chloro-3′-fluoro-1,1′-biphenyl-2-yl)-4-
(3-7) hexaconazole



(difluoromethyl)-2-methyl-1,3-thiazole-5-carboxamide



B-58
(1-9) N-(4′-chloro-3′-fluoro-1,1′-biphenyl-2-yl)-4-
(3-19) metconazole



(difluoromethyl)-2-methyl-1,3-thiazole-5-carboxamide



B-59
(1-9) N-(4′-chloro-3′-fluoro-1,1′-biphenyl-2-yl)-4-
(3-22) triadimenol



(difluoromethyl)-2-methyl-1,3-thiazole-5-carboxamide



B-60
(1-9) N-(4′-chloro-3′-fluoro-1,1′-biphenyl-2-yl)-4-
(3-24) fluquinconazole



(difluoromethyl)-2-methyl-1,3-thiazole-5-carboxamide



B-61
(1-9) N-(4′-chloro-3′-fluoro-1,1′-biphenyl-2-yl)-4-
(3-3) propiconazole



(difluoromethyl)-2-methyl-1,3-thiazole-5-carboxamide



B-62
(1-9) N-(4′-chloro-3′-fluoro-1,1′-biphenyl-2-yl)-4-
(3-6) cyproconazole



(difluoromethyl)-2-methyl-1,3-thiazole-5-carboxamide



B-63
(1-9) N-(4′-chloro-3′-fluoro-1,1′-biphenyl-2-yl)-4-
(3-15) prothioconazole



(difluoromethyl)-2-methyl-1,3-thiazole-5-carboxamide



B-64
(1-9) N-(4′-chloro-3′-fluoro-1,1′-biphenyl-2-yl)-4-
(3-17) tebuconazole



(difluoromethyl)-2-methyl-1,3-thiazole-5-carboxamide



B-65
(1-9) N-(4′-chloro-3′-fluoro-1,1′-biphenyl-2-yl)-4-
(3-21) bitertanol



(difluoromethyl)-2-methyl-1,3-thiazole-5-carboxamide









In addition to a carboxamide of the formula (I) (group 1), the active compound combinations C also comprise a sulphonamide of the formula (IV) (group 4)




embedded image



in which R22 is as defined above.


Preference is given to active compound combinations C in which the sulphonamide of the formula (IV) (group 4) is selected from the following list:

  • (4-1) dichlofluanid
  • (4-2) tolylfluanid


Emphasis is given to the active compound combinations C listed in Table 3 below:









TABLE 3







Active compound combinations C











Sulphenamide of


No.
Carboxamide of the formula (I)
the formula (IV)





C-1
(1-1) N-(3′,4′-dichloro-5-fluoro-1,1′-
(4-1) dichlofluanid



biphenyl-2-yl)-3-(difluoromethyl)-1-




methyl-1H-pyrazole-4-carboxamide



C-2
(1-1) N-(3′,4′-dichloro-5-fluoro-1,1′-
(4-2) tolylfluanid



biphenyl-2-yl)-3-(difluoromethyl)-1-




methyl-1H-pyrazole-4-carboxamide



C-3
(1-7) N-(4′-bromo-1,1′-biphenyl-2-yl)-
(4-1) dichlofluanid



4-(difluoromethyl)-2-methyl-1,3-




thiazole-5-carboxamide



C-4
(1-7) N-(4′-bromo-1,1′-biphenyl-2-yl)-
(4-2) tolylfluanid



4-(difluoromethyl)-2-methyl-1,3-




thiazole-5-carboxamide



C-5
(1-8) 4-(difluoromethyl)-2-methyl-N-
(4-1) dichlofluanid



[4′-(trifluoromethyl)-1,1′-biphenyl-2-yl]-




1,3-thiazole-5-carboxamide



C-6
(1-8) 4-(difluoromethyl)-2-methyl-N-
(4-2) tolylfluanid



[4′-(trifluoromethyl)-1,1′-biphenyl-2-yl]-




1,3-thiazole-5-carboxamide



C-7
(1-9) N-(4′-chloro-3′-fluoro-1,1′-biphenyl-
(4-1) dichlofluanid



2-yl)-4-(difluoromethyl)-2-methyl-1,3-




thiazole-5-carboxamide



C-8
(1-9) N-(4′-chloro-3′-fluoro-1,1′-biphenyl-
(4-2) tolylfluanid



2-yl)-4-(difluoromethyl)-2-methyl-1,3-




thiazole-5-carboxamide









In addition to a carboxamide of the formula (I) (group 1), the active compound combinations D also comprise a valinamide (group 5) selected from

  • (5-1) iprovalicarb
  • (5-2) N′-[2-(4-{[3-(4-chlorophenyl)-2-propynyl]oxy}-3-methoxyphenyl)ethyl]-N2-(methyl-sulphonyl)-D-valinamide
  • (5-3) benthiavalicarb


Preference is given to active compound combinations D in which the valinamide (group 5) is selected from the following list:

  • (5-1) iprovalicarb
  • (5-3) benthiavalicarb


Emphasis is given to the active compound combinations D listed in Table 4 below:









TABLE 4







Active compound combinations D









No.
Carboxamide of the formula (I)
Valinamide





D-1
(1-1) N-(3′,4′-dichloro-5-fluoro-1,1′-biphenyl-2-yl)-3-(difluoromethyl)-
(5-1) iprovalicarb



1-methyl-1H-pyrazole-4-carboxamide



D-2
(1-1) N-(3′,4′-dichloro-5-fluoro-1,1′-biphenyl-2-yl)-3-(difluoromethyl)-
(5-2) benthiavalicarb



1-methyl-1H-pyrazole-4-carboxamide



D-3
(1-7) N-(4′-bromo-1,1′-biphenyl-2-yl)-4-(difluoromethyl)-2-methyl-1,3-
(5-1) iprovalicarb



thiazole-5-carboxamide



D-4
(1-7) N-(4′-bromo-1,1′-biphenyl-2-yl)-4-(difluoromethyl)-2-methyl-1,3-
(5-2) benthiavalicarb



thiazole-5-carboxamide



D-5
(1-8) 4-(difluoromethyl)-2-methyl-N-[4′-(trifluoromethyl)-1,1′-
(5-1) iprovalicarb



biphenyl-2-yl]-1,3-thiazole-5-carboxamide



D-6
(1-8) 4-(difluoromethyl)-2-methyl-N-[4′-(trifluoromethyl)-1,1′-
(5-2) benthiavalicarb



biphenyl-2-yl]-1,3-thiazole-5-carboxamide



D-7
(1-9) N-(4′-chloro-3′-fluoro-1,1′-biphenyl-2-yl)-4-(difluoromethyl)-2-
(5-1) iprovalicarb



methyl-1,3-thiazole-5-carboxamide



D-8
(1-9) N-(4′-chloro-3′-fluoro-1,1′-biphenyl-2-yl)-4-(difluoromethyl)-2-
(5-2) benthiavalicarb



methyl-1,3-thiazole-5-carboxamide









In addition to a carboxamide of the formula (I) (group 1), the active compound combinations E also comprise a carboxamide of the formula (V) (group 6)




embedded image



in which X, Y and Z are as defined above.


Preference is given to active compound combinations E in which the carboxamide of the formula (V) (group 6) is selected from the list below:

  • (6-1) 2-chloro-N-(1,1,3-trimethylindan-4-yl)nicotinamide
  • (6-2) boscalid
  • (6-3) furametpyr
  • (6-4) N-(3-p-tolylthiophen-2-yl)-1-methyl-3-trifluoromethyl-1H-pyrazole-4-carboxamide
  • (6-5) ethaboxam
  • (6-6) fenhexamid
  • (6-7) carpropamid
  • (6-8) 2-chloro-4-(2-fluoro-2-methylpropionylamino)-N,N-dimethylbenzamide
  • (6-9) picobenzamid
  • (6-10) zoxamide
  • (6-11) 3,4-dichloro-N-(2-cyanophenyl)isothiazole-5-carboxamide
  • (6-12) carboxin
  • (6-13) tiadinil
  • (6-14) penthiopyrad
  • (6-15) silthiofam
  • (6-16) N-[2-(1,3-dimethylbutyl)phenyl]-1-methyl-4-(trifluoromethyl)-1H-pyrrole-3-carboxamide Particular preference is given to active compound combinations E in which the carboxamide of the formula (V) (group 6) is selected from the list below:
  • (6-2) boscalid
  • (6-5) ethaboxam
  • (6-6) fenhexamid
  • (6-7) carpropamid
  • (6-8) 2-chloro-4-(2-fluoro-2-methylpropionylamino)-N,N-dimethylbenzamide
  • (6-9) picobenzamid
  • (6-10) zoxamide
  • (6-11) 3,4-dichloro-N-(2-cyanophenyl)isothiazole-5-carboxamide
  • (6-14) penthiopyrad
  • (6-16) N-[2-(1,3-dimethylbutyl)phenyl]-1-methyl-4-(trifluoromethyl)-1H-pyrrole-3-carboxamide


Very particular preference is given to active compound combinations E in which the carboxamide of the formula (V) (group 6) is selected from the list below:

  • (6-2) boscalid
  • (6-6) fenhexamid
  • (6-7) carpropamid
  • (6-9) picobenzamid
  • (6-14) penthiopyrad


Emphasis is given to the active compound combinations E listed in Table 5 below:









TABLE 5







Active compound combinations E











Carboxamide of


No.
Carboxamide of the formula (I)
the formula (V)





E-1
(1-1) N-(3′,4′-dichloro-5-fluoro-1,1′-biphenyl-2-yl)-3-
(6-2) boscalid



(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide



E-2
(1-1) N-(3′,4′-dichloro-5-fluoro-1,1′-biphenyl-2-yl)-3-
(6-6) fenhexamid



(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide



E-3
(1-1) N-(3′,4′-dichloro-5-fluoro-1,1′-biphenyl-2-yl)-3-
(6-7) carpropamid



(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide



E-4
(1-1) N-(3′,4′-dichloro-5-fluoro-1,1′-biphenyl-2-yl)-3-
(6-9) picobenzamid



(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide



E-5
(1-1) N-(3′,4′-dichloro-5-fluoro-1,1′-biphenyl-2-yl)-3-
(6-14) penthiopyrad



(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide



E-6
(1-7) N-(4′-bromo-1,1′-biphenyl-2-yl)-4-(difluoromethyl)-
(6-2) boscalid



2-methyl-1,3-thiazole-5-carboxamide



E-7
(1-7) N-(4′-bromo-1,1′-biphenyl-2-yl)-4-(difluoromethyl)-
(6-6) fenhexamid



2-methyl-1,3-thiazole-5-carboxamide



E-8
(1-7) N-(4′-bromo-1,1′-biphenyl-2-yl)-4-(difluoromethyl)-
(6-7) carpropamid



2-methyl-1,3-thiazole-5-carboxamide



E-9
(1-7) N-(4′-bromo-1,1′-biphenyl-2-yl)-4-(difluoromethyl)-
(6-9) picobenzamid



2-methyl-1,3-thiazole-5-carboxamide



E-10
(1-7) N-(4′-bromo-1,1′-biphenyl-2-yl)-4-(difluoromethyl)-
(6-14) penthiopyrad



2-methyl-1,3-thiazole-5-carboxamide



E-11
(1-8) 4-(difluoromethyl)-2-methyl-N-[4′-(trifluoromethyl)-
(6-2) boscalid



1,1′-biphenyl-2-yl]-1,3-thiazole-5-carboxamide



E-12
(1-8) 4-(difluoromethyl)-2-methyl-N-[4′-(trifluoromethyl)-
(6-6) fenhexamid



1,1′-biphenyl-2-yl]-1,3-thiazole-5-carboxamide



E-13
(1-8) 4-(difluoromethyl)-2-methyl-N-[4′-(trifluoromethyl)-
(6-7) carpropamid



1,1′-biphenyl-2-yl]-1,3-thiazole-5-carboxamide



E-14
(1-8) 4-(difluoromethyl)-2-methyl-N-[4′-(trifluoromethyl)-
(6-9) picobenzamid



1,1′-biphenyl-2-yl]-1,3-thiazole-5-carboxamide



E-15
(1-8) 4-(difluoromethyl)-2-methyl-N-[4′-(trifluoromethyl)-
(6-14) penthiopyrad



1,1′-biphenyl-2-yl]-1,3-thiazole-5-carboxamide



E-16
(1-9) N-(4′-chloro-3′-fluoro-1,1′-biphenyl-2-yl)-4-
(6-2) boscalid



(difluoromethyl)-2-methyl-1,3-thiazole-5-carboxamide



E-17
(1-9) N-(4′-chloro-3′-fluoro-1,1′-biphenyl-2-yl)-4-
(6-6) fenhexamid



(difluoromethyl)-2-methyl-1,3-thiazole-5-carboxamide



E-18
(1-9) N-(4′-chloro-3′-fluoro-1,1′-biphenyl-2-yl)-4-
(6-7) carpropamid



(difluoromethyl)-2-methyl-1,3-thiazole-5-carboxamide



E-19
(1-9) N-(4′-chloro-3′-fluoro-1,1′-biphenyl-2-yl)-4-
(6-9) picobenzamid



(difluoromethyl)-2-methyl-1,3-thiazole-5-carboxamide



E-20
(1-9) N-(4′-chloro-3′-fluoro-1,1′-biphenyl-2-yl)-4-
(6-14) penthiopyrad



(difluoromethyl)-2-methyl-1,3-thiazole-5-carboxamide









In addition to a carboxamide of the formula (I) (group 1), the active compound combinations F also comprise a dithiocarbamate (group 7) selected from

  • (7-1) mancozeb
  • (7-2) maneb
  • (7-3) metiram
  • (7-4) propineb
  • (7-5) thiram
  • (7-6) zineb
  • (7-7) ziram


Preference is given to active compound combinations F in which the dithiocarbamate (group 7) is selected from the following list:

  • (7-1) mancozeb
  • (7-2) maneb
  • (7-4) propineb
  • (7-5) thiram
  • (7-6) zineb


Particular preference is given to active compound combinations F in which the dithiocarbamate (group 7) is selected from the following list:

  • (7-1) mancozeb
  • (7-4) propineb


Emphasis is given to the active compound combinations F listed in Table 6 below:









TABLE 6







Active compound combinations F









No.
Carboxamide of the formula (I)
Dithiocarbamate





F-1
(1-1) N-(3′,4′-dichloro-5-fluoro-1,1′-biphenyl-2-yl)-3-(difluoromethyl)-
(7-1) mancozeb



1-methyl-1H-pyrazole-4-carboxamide



F-2
(1-1) N-(3′,4′-dichloro-5-fluoro-1,1′-biphenyl-2-yl)-3-(difluoromethyl)-
(7-4) propineb



1-methyl-1H-pyrazole-4-carboxamide



F-3
(1-7) N-(4′-bromo-1,1′-biphenyl-2-yl)-4-(difluoromethyl)-2-methyl-1,3-
(7-1) mancozeb



thiazole-5-carboxamide



F-4
(1-7) N-(4′-bromo-1,1′-biphenyl-2-yl)-4-(difluoromethyl)-2-methyl-1,3-
(7-4) propineb



thiazole-5-carboxamide



F-5
(1-8) 4-(difluoromethyl)-2-methyl-N-[4′-(trifluoromethyl)-1,1′-
(7-1) mancozeb



biphenyl-2-yl]-1,3-thiazole-5-carboxamide



F-6
(1-8) 4-(difluoromethyl)-2-methyl-N-[4′-(trifluoromethyl)-1,1′
(7-4) propineb



biphenyl-2-yl]-1,3-thiazole-5-carboxamide



F-7
(1-9) N-(4′-chloro-3′-fluoro-1,1′-biphenyl-2-yl)-4-(difluoromethyl)-2-
(7-1) mancozeb



methyl-1,3-thiazole-5-carboxamide



F-8
(1-9) N-(4′-chloro-3′-fluoro-1,1′-biphenyl-2-yl)-4-(difluoromethyl)-2-
(7-4) propineb



methyl-1,3-thiazole-5-carboxamide









In addition to a carboxamide of the formula (I) (group 1), the active compound combinations G also comprise an acylalanine of the formula (VI) (group 8)




embedded image



in which * and R26 are as defined above.


Preference is given to active compound combinations G in which the acylalanine of the formula (VI) (group 8) is selected from the following list:

  • (8-1) benalaxyl
  • (8-2) furalaxyl
  • (8-3) metalaxyl
  • (8-4) metalaxyl-M
  • (8-5) benalaxyl-M


Particular preference is given to active compound combinations G in which the acylalanine of the formula (VI) (group 8) is selected from the following list:

  • (8-3) metalaxyl
  • (8-4) metalaxyl-M
  • (8-5) benalaxyl-M


Emphasis is given to the active compound combinations G listed in Table 7 below:









TABLE 7







Active compound combinations G











Acylalanine of


No.
Carboxamide of the formula (I)
the formula (VI)





G-1
(1-1) N-(3′,4′-dichloro-5-fluoro-1,1′-
(8-3) metalaxyl



biphenyl-2-yl)-3-(difluoromethyl)-1-




methyl-1H-pyrazole-4-carboxamide



G-2
(1-1) N-(3′,4′-dichloro-5-fluoro-1,1′-
(8-4) metalaxyl-M



biphenyl-2-yl)-3-(difluoromethyl)-1-




methyl-1H-pyrazole-4-carboxamide



G-3
(1-1) N-(3′,4′-dichloro-5-fluoro-1,1′-
(8-5) benalaxyl-M



biphenyl-2-yl)-3-(difluoromethyl)-1-




methyl-1H-pyrazole-4-carboxamide



G-4
(1-7) N-(4′-bromo-1,1′-biphenyl-2-yl)-
(8-3) metalaxyl



4-(difluoromethyl)-2-methyl-1,3-




thiazole-5-carboxamide



G-5
(1-7) N-(4′-bromo-1,1′-biphenyl-2-yl)-
(8-4) metalaxyl-M



4-(difluoromethyl)-2-methyl-1,3-




thiazole-5-carboxamide



G-6
(1-7) N-(4′-bromo-1,1′-biphenyl-2-yl)-
(8-5) benalaxyl-M



4-(difluoromethyl)-2-methyl-1,3-




thiazole-5-carboxamide



G-7
(1-8) 4-(difluoromethyl)-2-methyl-N-[4′-
(8-3) metalaxyl



(trifluoromethyl)-1,1′-biphenyl-2-yl]-




1,3-thiazole-5-carboxamide



G-8
(1-8) 4-(difluoromethyl)-2-methyl-N-[4′-
(8-4) metalaxyl-M



(trifluoromethyl)-1,1′-biphenyl-2-yl]-




1,3-thiazole-5-carboxamide



G-9
(1-8) 4-(difluoromethyl)-2-methyl-N-[4′-
(8-5) benalaxyl-M



(trifluoromethyl)-1,1′-biphenyl-2-yl]-




1,3-thiazole-5-carboxamide



G-10
(1-9) N-(4′-chloro-3′-fluoro-1,1′-biphenyl-
(8-3) metalaxyl



2-yl)-4-(difluoromethyl)-2-methyl-




1,3-thiazole-5-carboxamide



G-11
(1-9) N-(4′-chloro-3′-fluoro-1,1′-biphenyl-
(8-4) metalaxyl-M



2-yl)-4-(difluoromethyl)-2-methyl-




1,3-thiazole-5-carboxamide



G-12
(1-9) N-(4′-chloro-3′-fluoro-1,1′-biphenyl-
(8-5) benalaxyl-M



2-yl)-4-(difluoromethyl)-2-methyl-




1,3-thiazole-5-carboxamide









In addition to a carboxamide of the formula (I) (group 1), the active compound combinations H also comprise an anilinopyrimidine (group 9) selected from

  • (9-1) cyprodinil
  • (9-2) mepanipyrim
  • (9-3) pyrimethanil


Emphasis is given to the active compound combinations H listed in Table 8 below:









TABLE 8







Active compound combinations H









No.
Carboxamide of the formula (I)
Anilinopyrimidine





H-1
(1-1) N-(3′,4′-dichloro-5-fluoro-1,1′-
(9-1) cyprodinil



biphenyl-2-yl)-3-(difluoromethyl)-1-




methyl-1H-pyrazole-4-carboxamide



H-2
(1-1) N-(3′,4′-dichloro-5-fluoro-1,1′-
(9-2) mepanipyrim



biphenyl-2-yl)-3-(difluoromethyl)-1-




methyl-1H-pyrazole-4-carboxamide



H-3
(1-1) N-(3′,4′-dichloro-5-fluoro-1,1′-
(9-3) pyrimethanil



biphenyl-2-yl)-3-(difluoromethyl)-1-




methyl-1H-pyrazole-4-carboxamide



H-4
(1-7) N-(4′-bromo-1,1′-biphenyl-2-yl)-
(9-1) cyprodinil



4-(difluoromethyl)-2-methyl-1,3-




thiazole-5-carboxamide



H-5
(1-7) N-(4′-bromo-1,1′-biphenyl-2-yl)-
(9-2) mepanipyrim



4-(difluoromethyl)-2-methyl-1,3-




thiazole-5-carboxamide



H-6
(1-7) N-(4′-bromo-1,1′-biphenyl-2-yl)-
(9-3) pyrimethanil



4-(difluoromethyl)-2-methyl-1,3-




thiazole-5-carboxamide



H-7
(1-8) 4-(difluoromethyl)-2-methyl-N-
(9-1) cyprodinil



[4′-(trifluoromethyl)-1,1′-biphenyl-2-yl]-




1,3-thiazole-5-carboxamide



H-8
(1-8) 4-(difluoromethyl)-2-methyl-N-
(9-2) mepanipyrim



[4′-(trifluoromethyl)-1,1′-biphenyl-2-yl]-




1,3-thiazole-5-carboxamide



H-9
(1-8) 4-(difluoromethyl)-2-methyl-N-
(9-3) pyrimethanil



[4′-(trifluoromethyl)-1,1′-biphenyl-2-yl]-




1,3-thiazole-5-carboxamide



H-10
(1-9) N-(4′-chloro-3′-fluoro-1,1′-biphenyl-
(9-1) cyprodinil



2-yl)-4-(difluoromethyl)-2-methyl-




1,3-thiazole-5-carboxamide



H-11
(1-9) N-(4′-chloro-3′-fluoro-1,1′-biphenyl-
(9-2) mepanipyrim



2-yl)-4-(difluoromethyl)-2-methyl-




1,3-thiazole-5-carboxamide



H-12
(1-9) N-(4′-chloro-3′-fluoro-1,1′-biphenyl-
(9-3) pyrimethanil



2-yl)-4-(difluoromethyl)-2-methyl-




1,3-thiazole-5-carboxamide









In addition to a carboxamide of the formula (I) (group 1), the active compound combinations I also comprise a benzimidazole of the formula (VIII) (group 10)




embedded image



in which R28, R29, R30 and R31 are as defined above.


Preference is given to active compound combinations I in which the benzimidazole of the formula (VIII) (group 10) is selected form the following list:

  • (10-1) 6-chloro-5-[(3,5-dimethylisoxazol-4-yl)sulphonyl]-2,2-difluoro-5H-[1,3]dioxolo[4,5-f]-benzimidazole
  • (10-2) benomyl
  • (10-3) carbendazim
  • (10-4) chlorfenazole
  • (10-5) fuberidazole
  • (10-6) thiabendazole


Particular preference is given to active compound combinations I in which the benzimidazole of the formula (VIII) (group 10) is:

  • (10-3) carbendazim


Emphasis is given to the active compound combinations I listed in Table 9 below:









TABLE 9







Active compound combinations I











Benzimidazole of


No.
Carboxamide of the formula (I)
the formula (VIII)





I-1
(1-1) N-(3′,4′-dichloro-5-fluoro-1,1′-
(10-3) carbendazim



biphenyl-2-yl)-3-(difluoromethyl)-1-




methyl-1H-pyrazole-4-carboxamide



I-2
(1-7) N-(4′-bromo-1,1′-biphenyl-2-yl)-
(10-3) carbendazim



4-(difluoromethyl)-2-methyl-1,3-




thiazole-5-carboxamide



I-3
(1-8) 4-(difluoromethyl)-2-methyl-N-
(10-3) carbendazim



[4′-(trifluoromethyl)-1,1′-biphenyl-2-yl]-




1,3-thiazole-5-carboxamide



I-4
(1-9) N-(4′-chloro-3′-fluoro-1,1′-
(10-3) carbendazim



biphenyl-2-yl)-4-(difluoromethyl)-2-




methyl-1,3-thiazole-5-carboxamide









In addition to a carboxamide of the formula (I) (group 1), the active compound combinations J also comprise a carbamate (group 11) of the formula (IX)




embedded image



in which R32 and R33 are as defined above.


Preference is given to active compound combinations J in which the carbamate (group 11) is selected from the following list:

  • (11-1) diethofencarb
  • (11-2) propamocarb
  • (11-3) propamocarb-hydrochloride
  • (11-4) propamocarb-fosetyl


Emphasis is given to the active compound combinations J listed in Table 10 below:









TABLE 10







Active compound combinations J











Carbamate


No.
Carboxamide of the formula (I)
of the formula (IX)





J-1
(1-1) N-(3′,4′-dichloro-5-fluoro-1,1′-biphenyl-2-yl)-3-
(11-2) propamocarb



(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide



J-2
(1-1) N-(3′,4′-dichloro-5-fluoro-1,1′-biphenyl-2-yl)-3-
(11-3) propamocarb-



(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide
hydrochloride


J-3
(1-1) N-(3′,4′-dichloro-5-fluoro-1,1′-biphenyl-2-yl)-3-
(11-4) propamocarb-fosetyl



(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide



J-4
(1-7) N-(4′-bromo-1,1′-biphenyl-2-yl)-4-(difluoromethyl)-
(11-2) propamocarb



2-methyl-1,3-thiazole-5-carboxamide



J-5
(1-7) N-(4′-bromo-1,1′-biphenyl-2-yl)-4-(difluoromethyl)-
(11-3) propamocarb-



2-methyl-1,3-thiazole-5-carboxamide
hydrochloride


J-6
(1-7) N-(4′-bromo-1,1′-biphenyl-2-yl)-4-(difluoromethyl)-
(11-4) propamocarb-fosetyl



2-methyl-1,3-thiazole-5-carboxamide



J-7
(1-8) 4-(difluoromethyl)-2-methyl-N-[4′-(trifluoromethyl)-
(11-2) propamocarb



1,1′-biphenyl-2-yl]-1,3-thiazole-5-carboxamide



J-8
(1-8) 4-(difluoromethyl)-2-methyl-N-[4′-(trifluoromethyl)-
(11-3) propamocarb-



1,11-biphenyl-2-yl]-1,3-thiazole-5-carboxamide
hydrochloride


J-9
(1-8) 4-(difluoromethyl)-2-methyl-N-[4′-(trifluoromethyl)-
(11-4) propamocarb-fosetyl



1,1′-biphenyl-2-yl]-1,3-thiazole-5-carboxamide



J-10
(1-9) N-(4′-chloro-3′-fluoro-1,1′-biphenyl-2-yl)-4-
(11-2) propamocarb



(difluoromethyl)-2-methyl-1,3-thiazole-5-carboxamide



J-11
(1-9) N-(4′-chloro-3′-fluoro-1,1′-biphenyl-2-yl)-4-
(11-3) propamocarb-



(difluoromethyl)-2-methyl-1,3-thiazole-5-carboxamide
hydrochloride


J-12
(1-9) N-(4′-chloro-3′-fluoro-1,1′-biphenyl-2-yl)-4-
(11-4) propamocarb-fosetyl



(difluoromethyl)-2-methyl-1,3-thiazole-5-carboxamide









In addition to a carboxamide of the formula (I) (group 1), the active compound combinations K also comprise a dicarboximide (group 12) selected from

  • (12-1) captafol
  • (12-2) captan
  • (12-3) folpet
  • (12-4) iprodione
  • (12-5) procymidone
  • (12-6) vinclozolin


Preference is given to active compound combinations K in which the dicarboximide (group 12) is selected from the following list:

  • (12-2) captan
  • (12-3) folpet
  • (12-4) iprodione


Emphasis is given to the active compound combinations K listed in Table 11 below:









TABLE 11







Active compound combinations K









No.
Carboxamide of the formula (I)
Dicarboximide





K-1
(1-1) N-(3′,4′-dichloro-5-fluoro-1,1′-biphenyl-2-yl)-3-(difluoromethyl)-
(12-2) captan



1-methyl-1H-pyrazole-4-carboxamide



K-2
(1-1) N-(3′,4′-dichloro-5-fluoro-1,1′-biphenyl-2-yl)-3-(difluoromethyl)-
(12-3) folpet



1-methyl-1H-pyrazole-4-carboxamide



K-3
(1-1) N-(3′,4′-dichloro-5-fluoro-1,1′-biphenyl-2-yl)-3-(difluoromethyl)-
(12-4) iprodione



1-methyl-1H-pyrazole-4-carboxamide



K-4
(1-7) N-(4′-bromo-1,1′-biphenyl-2-yl)-4-(difluoromethyl)-2-methyl-1,3-
(12-2) captan



thiazole-5-carboxamide



K-5
(1-7) N-(4′-bromo-1,1′-biphenyl-2-yl)-4-(difluoromethyl)-2-methyl-1,3-
(12-3) folpet



thiazole-5-carboxamide



K-6
(1-7) N-(4′-bromo-1,1′-biphenyl-2-yl)-4-(difluoromethyl)-2-methyl-1,3-
(12-4) iprodione



thiazole-5-carboxamide



K-7
(1-8) 4-(difluoromethyl)-2-methyl-N-[4′-(trifluoromethyl)-1,1′-
(12-2) captan



biphenyl-2-yl]-1,3-thiazole-5-carboxamide



K-8
(1-8) 4-(difluoromethyl)-2-methyl-N-[4′-(trifluoromethyl)-1,1′-
(12-3) folpet



biphenyl-2-yl]-1,3-thiazole-5-carboxamide



K-9
(1-8) 4-(difluoromethyl)-2-methyl-N-[4′-(trifluoromethyl)-1,1′-
(12-4) iprodione



biphenyl-2-y11-1,3-thiazole-5-carboxamide



K-10
(1-9) N-(4′-chloro-3′-fluoro-1,1′-biphenyl-2-yl)-4-(difluoromethyl)-2-
(12-2) captan



methyl-1,3-thiazole-5-carboxamide



K-11
(1-9) N-(4′-chloro-3′-fluoro-1,1′-biphenyl-2-yl)-4-(difluoromethyl)-2-
(12-3) folpet



methyl-1,3-thiazole-5-carboxamide



K-12
(1-9) N-(4′-chloro-3′-fluoro-1,1′-biphenyl-2-yl)-4-(difluoromethyl)-2-
(12-4) iprodione



methyl-1,3-thiazole-5-carboxamide









In addition to a carboxamide of the formula (I) (group 1), the active compound combinations L also comprise a guanidine (group 13) selected from

  • (13-1) dodine
  • (13-2) guazatine
  • (13-3) iminoctadine triacetate
  • (13-4) iminoctadine tris(albesilate)


Preference is given to active compound combinations L in which the guanidine (group 13) is selected from the following list:

  • (13-1) dodine
  • (13-2) guazatine


Emphasis is given to the active compound combinations L listed in Table 12 below:









TABLE 12







Active compound combinations L









No.
Carboxamide of the formula (I)
Guanidine





L-1
(1-1) N-(3′,4′-dichloro-5-fluoro-1,1′-biphenyl-2-yl)-3-(difluoromethyl)-
(13-1) dodine



1-methyl-1H-pyrazole-4-carboxamide



L-2
(1-1) N-(3′,4′-dichloro-5-fluoro-1,1′-biphenyl-2-yl)-3-(difluoromethyl)-
(13-2) guazatine



1-methyl-1H-pyrazole-4-carboxamide



L-3
(1-7) N-(4′-bromo-1,1′-biphenyl-2-yl)-4-(difluoromethyl)-2-methyl-1,3-
(13-1) dodine



thiazole-5 -carboxamide



L-4
(1-7) N-(4′-bromo-1,1′-biphenyl-2-yl)-4-(difluoromethyl)-2-methyl-1,3-
(13-2) guazatine



thiazole-5-carboxamide



L-5
(1-8) 4-(difluoromethyl)-2-methyl-N-[4′-(trifluoromethyl)-1,1′-
(13-1) dodine



biphenyl-2-yl]-1,3-thiazole-5-carboxamide



L-6
(1-8) 4-(difluoromethyl)-2-methyl-N-[4′-(trifluoromethyl)-1,1′-
(13-2) guazatine



biphenyl-2-yl]-1,3-thiazole-5-carboxamide



L-7
(1-9) N-(4′-chloro-3′-fluoro-1,1′-biphenyl-2-yl)-4-(difluoromethyl)-2-
(13-1) dodine



methyl-1,3-thiazole-5-carboxamide



L-8
(1-9) N-(4′-chloro-3′-fluoro-1,1′-biphenyl-2-yl)-4-(difluoromethyl)-2-




methyl-1,3-thiazole-5-carboxamide
(13-2) guazatine









In addition to a carboxamide of the formula (I) (group 1), the active compound combinations M also comprise an imidazole (group 14) selected from

  • (14-1) cyazofamid
  • (14-2) prochloraz
  • (14-3) triazoxide
  • (14-4) pefurazoate


Preference is given to active compound combinations M in which the imidazole (group 14) is selected from the following list:

  • (14-2) prochloraz
  • (14-3) triazoxide


Emphasis is given to the active compound combinations M listed in Table 13 below:









TABLE 13







Active compound combinations M









No.
Carboxamide of the formula (I)
Imidazole





M-1
(1-1) N-(3′,4′-dichloro-5-fluoro-1,1′-biphenyl-2-yl)-3-(difluoromethyl)-
(14-2) prochloraz



1-methyl-1H-pyrazole-4-carboxamide



M-2
(1-1) N-(3′,4′-dichloro-5-fluoro-1,1′-biphenyl-2-yl)-3-(difluoromethyl)-
(14-3) triazoxide



1-methyl-1H-pyrazole-4-carboxamide



M-3
(1-7) N-(4′-bromo-1,1′-biphenyl-2-yl)-4-(difluoromethyl)-2-methyl-1,3-
(14-2) prochloraz



thiazole-5 -carboxamide



M-4
(1-7) N-(4′-bromo-1,1′-biphenyl-2-yl)-4-(difluoromethyl)-2-methyl-1,3-
(14-3) triazoxide



thiazole-5-carboxamide



M-5
(1-8) 4-(difluoromethyl)-2-methyl-N-[4′-(trifluoromethyl)-1,1′-
(14-2) prochloraz



biphenyl-2-yl]-1,3-thiazole-5-carboxamide



M-6
(1-8) 4-(difluoromethyl)-2-methyl-N-[4′-(trifluoromethyl)-1,1′-
(14-3) triazoxide



biphenyl-2-yl]-1,3-thiazole-5-carboxamide



M-7
(1-9) N-(4′-chloro-3′-fluoro-1,1′-biphenyl-2-yl)-4-(difluoromethyl)-2-
(14-2) prochloraz



methyl-1,3-thiazole-5-carboxamide



M-8
(1-9) N-(4′-chloro-3′-fluoro-1,1′-biphenyl-2-yl)-4-(difluoromethyl)-2-
(14-3) triazoxide



methyl-1,3-thiazole-5-carboxamide









In addition to a carboxamide of the formula (I) (group 1), the active compound combinations N also comprise a morpholine (group 15) of the formula (X)




embedded image



in which R34, R35 and R36 are as defined above.


Preference is given to active compound combinations N in which the morpholine (group 15) of the formula (X) is selected from the following list:

  • (15-1) aldimorph
  • (15-2) tridemorph
  • (15-3) dodemorph
  • (15-4) fenpropimorph
  • (15-5) dimethomorph


Particular preference is given to active compound combinations N in which the morpholine (group 15) of the formula (X) is selected from the following list:

  • (15-4) fenpropimorph
  • (15-5) dimethomorph


Emphasis is given to the active compound combinations N listed in Table 14 below:









TABLE 14







Active compound combinations N











Morpholine of


No.
Carboxamide of the formula (I)
the formula (X)





N-1
(1-1) N-(3′,4′-dichloro-5-fluoro-1,1′-biphenyl-2-yl)-3-
(15-4) fenpropimorph



(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide



N-2
(1-7) N-(4′-bromo-1,1′-biphenyl-2-yl)-4-(difluoromethyl)-
(15-4) fenpropimorph



2-methyl-1,3-thiazole-5-carboxamide



N-3
(1-8) 4-(difluoromethyl)-2-methyl-N-[4′-(trifluoromethyl)-
(15-4) fenpropimorph



1,1′-biphenyl-2-yl]-1,3-thiazole-5-carboxamide



N-4
(1-9) N-(4′-chloro-3′-fluoro-1,1′-biphenyl-2-yl)-4-
(15-4) fenpropimorph



(difluoromethyl)-2-methyl-1,3-thiazole-5-carboxamide









In addition to a carboxamide of the formula (I) (group 1), the active compound combinations 0 also comprise a pyrrole (group 16) of the formula (XI)




embedded image



in which R37, R38 and R39 are as defined above.


Preference is given to active compound combinations 0 in which the pyrrole (group 16) of the formula (XI) is selected from the following list:

  • (16-1) fenpiclonil
  • (16-2) fludioxonil
  • (16-3) pyrrolnitrin


Particular preference is given to active compound combinations 0 in which the pyrrole (group 16) of the formula (XI) is selected from the following list:

  • (16-2) fludioxonil


Emphasis is given to the active compound combinations 0 listed in Table 15 below:









TABLE 15







Active compound combinations O











Pyrrole of


No.
Carboxamide of the formula (I)
the formula (XI)





O-1
(1-1) N-(3′,4′-dichloro-5-fluoro-1,1′-
(16-2) fludioxonil



biphenyl-2-yl)-3-(difluoromethyl)-1-




methyl-1H-pyrazole-4-carboxamide



O-2
(1-7) N-(4′-bromo-1,1′-biphenyl-2-yl)-
(16-2) fludioxonil



4-(difluoromethyl)-2-methyl-1,3-




thiazole-5-carboxamide



O-3
(1-8) 4-(difluoromethyl)-2-methyl-N-
(16-2) fludioxonil



[4′-(trifluoromethyl)-1,1′-biphenyl-2-yl]-




1,3-thiazole-5-carboxamide



O-4
(1-9) N-(4′-chloro-3′-fluoro-1,1′-
(16-2) fludioxonil



biphenyl-2-yl)-4-(difluoromethyl)-2-




methyl-1,3-thiazole-5-carboxamide









In addition to a carboxamide of the formula (I) (group 1), the active compound combinations P also comprise a phosphonate (group 17) selected from

  • (17-1) fosetyl-Al
  • (17-2) phosphonic acid


Emphasis is given to the active compound combinations P listed in Table 16 below:









TABLE 16







Active compound combinations P









No.
Carboxamide of the formula (I)
Phosphonate





P-1
(1-1) N-(3′,4′-dichloro-5-fluoro-1,1′-
(17-1) fosetyl-Al



biphenyl-2-yl)-3-(difluoromethyl)-1-




methyl-1H-pyrazole-4-carboxamide



P-2
(1-7) N-(4′-bromo-1,1′-biphenyl-2-yl)-
(17-1) fosetyl-Al



4-(difluoromethyl)-2-methyl-1,3-




thiazole-5-carboxamide



P-3
(1-8) 4-(difluoromethyl)-2-methyl-N-
(17-1) fosetyl-Al



[4′-(trifluoromethyl)-1,1′-biphenyl-2-yl]-




1,3-thiazole-5-carboxamide



P-4
(1-9) N-(4′-chloro-3′-fluoro-1,1′-
(17-1) fosetyl-Al



biphenyl-2-yl)-4-(difluoromethyl)-2-




methyl-1,3-thiazole-5-carboxamide









In addition to a carboxamide of the formula (I) (group 1), the active compound combinations Q also comprise a fungicide (group 19) selected from

  • (19-1) acibenzolar-S-methyl
  • (19-2) chlorothalonil
  • (19-3) cymoxanil
  • (19-4) edifenphos
  • (19-5) famoxadone
  • (19-6) fluazinam
  • (19-7) copper oxychloride
  • (19-8) copper hydroxide
  • (19-9) oxadixyl
  • (19-10) spiroxamine
  • (19-11) dithianon
  • (19-12) metrafenone
  • (19-13) fenamidone
  • (19-14) 2,3-dibutyl-6-chlorothieno[2,3-d]pyrimidin-4(3H)one
  • (19-15) probenazole
  • (19-16) isoprothiolane
  • (19-17) kasugamycin
  • (19-18) phthalide
  • (19-19) ferimzone
  • (19-20) tricyclazole
  • (19-21) N-({4-[(cyclopropylamino)carbonyl]phenyl}sulphonyl)-2-methoxybenzamide
  • (19-22) 2-(4-chlorophenyl)-N-{2-[3-methoxy-4-(prop-2-yn-1-yloxy)phenyl]ethyl}-2-(prop-2-yn-1-yloxy)acetamide


Preference is given to active compound combinations Q in which the fungicide (group 19) is selected from the following list:

  • (19-1) acibenzolar-S-methyl
  • (19-2) chlorothalonil
  • (19-3) cymoxanil
  • (19-5) famoxadone
  • (19-6) fluazinam
  • (19-7) copper oxychloride
  • (19-9) oxadixyl
  • (19-10) spiroxamine
  • (19-13) fenamidone
  • (19-21) N-({4-[(cyclopropylamino)carbonyl]phenyl}sulphonyl)-2-methoxybenzamide
  • (19-22) 2-(4-chlorophenyl)-N-{2-[3-methoxy-4-(prop-2-yn-1-yloxy)phenyl]ethyl}-2-(prop-2-yn-1-yloxy)acetamide


Particular preference is given to active compound combinations Q in which the fungicide (group 19) is selected from the following list:

  • (19-2) chlorothalonil
  • (19-7) copper oxychloride
  • (19-10) spiroxamine
  • (19-21) N-({4-[(cyclopropylamino)carbonyl]phenyl}sulphonyl)-2-methoxybenzamide
  • (19-22) 2-(4-chlorophenyl)-N-{2-[3-methoxy-4-(prop-2-yn-1-yloxy)phenyl]ethyl}-2-(prop-2-yn-1-yloxy)acetamide


Emphasis is given to the active compound combinations Q listed in Table 17 below:









TABLE 17







Active compound combinations Q









No.
Carboxamide of the formula (I)
Fungicide





Q-1
(1-1) N-(3′,4′-dichloro-5-fluoro-1,1′-biphenyl-2-yl)-3-
(19-2) chlorothalonil



(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide



Q-2
(1-1) N-(3′,4′-dichloro-5-fluoro-1,1′-biphenyl-2-yl)-3-
(19-7) copper oxychloride



(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide



Q-3
(1-1) N-(3′,4′-dichloro-5-fluoro-1,1′-biphenyl-2-yl)-3-
(19-10) spiroxamine



(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide



Q-4
(1-1) N-(3′,4′-dichloro-5-fluoro-1,1′-biphenyl-2-yl)-3-
(19-21) N-({4-[(cyclopropylamino)-



(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide
carbonyl]phenyl}sulphonyl)-2-




methoxybenzamide


Q-5
(1-1) N-(3′,4′-dichloro-5-fluoro-1,1′-biphenyl-2-yl)-3-
(19-22) 2-(4-chlorophenyl)-N-{2-[3-



(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide
methoxy-4-(prop-2-yn-1-yloxy)phenyl]-




ethyl}-2-(prop-2-yn-1-yloxy)acetamide


Q-6
(1-7) N-(4′-bromo-1,1′-biphenyl-2-yl)-4-(difluoromethyl)-
(19-2) chlorothalonil



2-methyl-1,3-thiazole-5-carboxamide



Q-7
(1-7) N-(4′-bromo-1,1′-biphenyl-2-yl)-4-(difluoromethyl)-
(19-7) copper oxychloride



2-methyl-1,3-thiazole-5-carboxamide



Q-8
(1-7) N-(4′-bromo-1,1′-biphenyl-2-yl)-4-(difluoromethyl)-
(19-10) spiroxamine



2-methyl-1,3-thiazole-5-carboxamide



Q-9
(1-7) N-(4′-bromo-1,1′-biphenyl-2-yl)-4-(difluoromethyl)-
(19-21) N-({4-[(cyclopropylamino)-



2-methyl-1,3-thiazole-5-carboxamide
carbonyl]phenyl}sulphonyl)-2-


Q-10
(1-7) N-(4′-bromo-1,1′-biphenyl-2-yl)-4-(difluoromethyl)-
(19-22) 2-(4-chloropheny1)-N-{2-[3



2-methyl-1,3-thiazole-5-carboxamide
methoxy-4-(prop-2-yn-1-yloxy)phenyl]-




ethyl}-2-(prop-2-yn-1-yloxy)acetamide


Q-11
(1-8) 4-(difluoromethyl)-2-methyl-N-[4′-(trifluoromethyl)-
(19-2) chlorothalonil



1,1′-biphenyl-2-yl]-1,3-thiazole-5-carboxamide



Q-12
(1-8) 4-(difluoromethyl)-2-methyl-N-[4′-(trifluoromethyl)-
(19-7) copper oxychloride



1,1′-biphenyl-2-yl]-1,3-thiazole-5-carboxamide



Q-13
(1-8) 4-(difluoromethyl)-2-methyl-N-[4′-(trifluoromethyl)-
(19-10) spiroxamine



1,1′-biphenyl-2-yl]-1,3-thiazole-5-carboxamide



Q-14
(1-8) 4-(difluoromethyl)-2-methyl-N-[4′-(trifluoromethyl)-
(19-21) N-({4-(cyclopropylamino)-



1,1′-biphenyl-2-yl]-1,3-thiazole-5-carboxamide
carbonyl]phenyl}sulphonyl)-2-




methoxybenzamide


Q-15
(1-8) 4-(difluoromethyl)-2-methyl-N-[4′-(trifluoromethyl)-
(19-22) 2-(4-chlorophenyl)-N-{2-[3-



1,1′-biphenyl-2-yl]-1,3-thiazole-5-carboxamide
methoxy-4-(prop-2-yn-1-yloxy)phenyl]-




ethyl}-2-(prop-2-yn-1-yloxy)acetamide


Q-16
(1-9) N-(4′-chloro-3′-fluoro-1,1′-biphenyl-2-yl)-4-
(19-2) chlorothalonil



(difluoromethyl)-2-methyl-1,3-thiazole-5-carboxamide



Q-17
(1-9) N-(4′-chloro-3′-fluoro-1,1′-biphenyl-2-yl)-4-
(19-7) copper oxychloride



(difluoromethyl)-2-methyl-1,3-thiazole-5-carboxamide



Q-18
(1-9) N-(4′-chloro-3′-fluoro-1,1′-biphenyl-2-yl)-4-
(19-10) spiroxamine



(difluoromethyl)-2-methyl-1,3-thiazole-5-carboxamide



Q-19
(1-9) N-(4′-chloro-3′-fluoro-1,1′-biphenyl-2-yl)-4-
(19-21) N-({4-[(cyclopropylamino)-



(difluoromethyl)-2-methyl-1,3-thiazole-5-carboxamide
carbonyl]phenyl}sulphonyl)-2-




methoxybenzamide


Q-20
(1-9) N-(4′-chloro-3′-fluoro-1,1′-biphenyl-2-yl)-4-
(19-22) 2-(4-chlorophenyl)-N-{2-[3-



(difluoromethyl)-2-methyl-1,3-thiazole-5-carboxamide
methoxy-4-(prop-2-yn-1-yloxy)phenyl]-




ethyl}-2-(prop-2-yn-1-yloxy)acetamide









In addition to a carboxamide of the formula (I) (group 1), the active compound combinations R also comprise a (thio)urea derivative (group 20) selected from

  • (20-1) pencycuron
  • (20-2) thiophanate-methyl
  • (20-3) thiophanate-ethyl


Preference is given to active compound combinations R in which the (thio)urea derivative (group 20) is selected from the following list:

  • (20-1) pencycuron
  • (20-2) thiophanate-methyl


Emphasis is given to the active compound combinations R listed in Table 18 below:









TABLE 18







Active compound combinations R









No.
Carboxamide of the formula (I)
(Thio)urea derivative





R-1
(1-1) N-(3′,4′-dichloro-5-fluoro-1,1′-
(20-1) pencycuron



biphenyl-2-yl)-3-(difluoromethyl)-1-




methyl-1H-pyrazole-4-carboxamide



R-2
(1-7) N-(4′-bromo-1,1′-biphenyl-2-yl)-
(20-1) pencycuron



4-(difluoromethyl)-2-methyl-1,3-thiazole-




5-carboxamide



R-3
(1-8) 4-(difluoromethyl)-2-methyl-N-[4′-
(20-1) pencycuron



(trifluoromethyl)-1,1′-biphenyl-2-yl]-




1,3-thiazole-5-carboxamide



R-4
(1-9) N-(4′-chloro-3′-fluoro-1,1′-
(20-1) pencycuron



biphenyl-2-yl)-4-(difluoromethyl)-2-




methyl-1,3-thiazole-5-carboxamide









In addition to a carboxamide of the formula (I) (group 1), the active compound combinations S also comprise a triazolopyrimidine (group 22) of the formula (XIV)




embedded image



in which R43, R44, R45, R46, R47, R48, R49 and R50 are as defined above.


Preference is given to active compound combinations S in which the triazolopyrimidine (group 22) of the formula (XIV) is selected from the list below:

  • (22-1) 5-chloro-N-[(1S)-2,2,2-trifluoro-1-methylethyl]-6-(2,4,6-trifluorophenyl)[1,2,4]triazolo-[1,5-a]pyrimidine-7-amine
  • (22-2) 5-chloro-N-[(1R)-1,2-dimethylpropyl]-6-(2,4,6-trifluorophenyl)[1,2,4]triazolo[1,5-a]-pyrimidine-7-amine
  • (22-3) 5-chloro-6-(2-chloro-6-fluorophenyl)-7-(4-methylpiperidin-1-yl)[1,2,4]triazolo[1,5-a]-pyrimidine
  • (22-4) 5-chloro-6-(2,4,6-trifluorophenyl)-7-(4-methylpiperidin-1-yl)[1,2,4]triazolo[1,5-a]pyrimidine


Particular preference is given to active compound combinations S in which the triazolopyrimidine (group 22) of the formula (XIV) is selected from the list below:

  • (22-1) 5-chloro-N-[(1S)-2,2,2-trifluoro-1-methylethyl]-6-(2,4,6-trifluorophenyl)[1,2,4]triazolo-[1,5-a]pyrimidine-7-amine
  • (22-2) 5-chloro-N—[(R)-1,2-dimethylpropyl]-6-(2,4,6-trifluorophenyl)[1,2,4]triazolo[1,5-a]-pyrimidine-7-amine
  • (22-4) 5-chloro-6-(2,4,6-trifluorophenyl)-7-(4-methylpiperidin-1-yl)[1,2,4]triazolo[1,5-a]pyrimidine


Emphasis is given to the active compound combinations S listed in Table 19 below:









TABLE 19







Active compound combinations S









No.
Carboxamide of the formula (I)
Triazolopyrimidine of the formula (XIV)





S-1
(1-1) N-(3′,4′-dichloro-5-fluoro-1,1′-
(22-1) 5-chloro-N-[(1S)-2,2,2-trifluoro-1-



biphenyl-2-yl)-3-(difluoromethyl)-1-
methylethyl]-6-(2,4,6-trifluorophenyl)-



methyl-1H-pyrazole-4-carboxamide
[1,2,4]triazolo[1,5-a]pyrimidine-7-amine


S-2
(1-1) N-(3′,4′-dichloro-5-fluoro-1,1′-
(22-2) 5-chloro-N-[(1R)-1,2-dimethylpropyl]-6-



biphenyl-2-yl)-3-(difluoromethyl)-1-
(2,4,6-trifluorophenyl)[1,2,4]triazolo[1,5-a]-



methyl-1H-pyrazole-4-carboxamide
pyrimidine-7-amine


S-3
(1-1) N-(3′,4′-dichloro-5-fluoro-1,1′-
(22-4) 5-chloro-6-(2,4,6-trifluorophenyl)-7-(4-



biphenyl-2-yl)-3-(difluoromethyl)-1-
methylpiperidin-1-yl)[1,2,4]triazolo[1,5-a]pyri-



methyl-1H-pyrazole-4-carboxamide
midine


S-4
(1-7) N-(4′-bromo-1,1′-biphenyl-2-yl)-4-
(22-1) 5-chloro-N-[(1S)-2,2,2-trifluoro-1-



(difluoromethyl)-2-methyl-1,3-thiazole-5-
methylethyl]-6-(2,4,6-trifluorophenyl)-



carboxamide
[1,2,4]triazolo[1,5-a]pyrimidine-7-amine


S-5
(1-7) N-(4′-bromo-1,1′-biphenyl-2-yl)-4-
(22-2) 5-chloro-N-[(1R)-1,2-dimethylpropyl]-6-



(difluoromethyl)-2-methyl-1,3-thiazole-5-
(2,4,6-trifluorophenyl)[1,2,4]triazolo[1,5-a]-



carboxamide
pyrimidine-7-amine


S-6
(1-7) N-(4′-bromo-1,1′-biphenyl-2-yl)-4-
(22-4) 5-chloro-6-(2,4,6-trifluorophenyl)-7-(4-



(difluoromethyl)-2-methyl-1,3-thiazole-5-
methylpiperidin-1-yl)[1,2,4]triazolo[1,5-a]pyri-



carboxamide
midine


S-7
(1-8) 4-(difluoromethyl)-2-methyl-N[4′-
(22-1) 5-chloro-N-[(1S)-2,2,2-trifluoro-1-



(trifluoromethyl)-1,1′-biphenyl-2-yl]-1,3-
methylethyl]-6-(2,4,6-trifluorophenyl)-



thiazole-5-carboxamide
[1,2,4]triazolo[1,5-a]pyrimidine-7-amine


S-8
(1-8) 4-(difluoromethyl)-2-methyl-N[4′-
(22-2) 5-chloro-N-[(1R)-1,2-dimethylpropyl]-6-



(trifluoromethyl)-1,1′-biphenyl-2-yl]-1,3-
(2,4,6-trifluorophenyl)[1,2,4]triazolo[1,5-a]-



thiazole-5-carboxamide
pyrimidine-7-amine


S-9
(1-8) 4-(difluoromethyl)-2-methyl-N[4′-
(22-4) 5-chloro-6-(2,4,6-trifluorophenyl)-7-(4-



(trifluoromethyl)-1,1′-biphenyl-2-yl]-1,3-
methylpiperidin-1-yl)[1,2,4]triazolo[1,5-a]pyri-



thiazole-5-carboxamide
midine


S-10
(1-9) N-(4′-chloro-3′-fluoro-1,1′-biphenyl-2-
(22-1) 5-chloro-N-[(1S)-2,2,2-trifluoro-1-



yl)-4-(difluoromethyl)-2-methyl-1,3-
methylethyl]-6-(2,4,6-trifluorophenyl)-



thiazole-5-carboxamide
[1,2,4]triazolo[1,5-a]pyrimidine-7-amine


S-11
(1-9) N-(4′-chloro-3′-fluoro-1,1′-biphenyl-2-
(22-2) 5-chloro-N-[(1R)-1,2-dimethylpropyl]-6-



yl)-4-(difluoromethyl)-2-methyl-1,3-
(2,4,6-trifluorophenyl)[1,2,4]triazolo[1,5-a]-



thiazole-5-carboxamide
pyrimidine-7-amine


S-12
(1-9) N-(4′-chloro-3′-fluoro-1,1′-biphenyl-2-
(22-4) 5-chloro-6-(2,4,6-trifluorophenyl)-7-(4-



yl)-4-(difluoromethyl)-2-methyl-1,3-
methylpiperidin-1-yl)[1,2,4]triazolo[1,5-a]pyri-



thiazole-5-carboxamide
midine









In addition to a carboxamide of the formula (I) (group 1), the active compound combinations T also comprise an iodochromone (group 23) of the formula (XV)




embedded image



in which R51 and R52 are as defined above.


Preference is given to active compound combinations T in which the iodochromone (group 23) of the formula (XV) is selected from the following list:

  • (23-1) 2-butoxy-6-iodo-3-propylbenzopyran-4-one
  • (23-2) 2-ethoxy-6-iodo-3-propylbenzopyran-4-one
  • (23-3) 6-iodo-2-propoxy-3-propylbenzopyran-4-one
  • (23-4) 2-but-2-ynyloxy-6-iodo-3-propylbenzopyran-4-one
  • (23-5) 6-iodo-2-(1-methylbutoxy)-3-propylbenzopyran-4-one
  • (23-6) 2-but-3-enyloxy-6-iodobenzopyran-4-one
  • (23-7) 3-butyl-6-iodo-2-isopropoxybenzopyran-4-one


Particular preference is given to active compound combinations T in which the iodochromone (group 23) of the formula (XV) is selected from the following list:

  • (23-1) 2-butoxy-6-iodo-3-propylbenzopyran-4-one
  • (23-2) 2-ethoxy-6-iodo-3-propylbenzopyran-4-one


Emphasis is given to the active compound combinations T listed in Table 20 below:









TABLE 20







Active compound combinations T











Iodochromone of the


No.
Carboxamide of the formula (I)
formula (XV)





T-1
(1-1) N-(3′,4′-dichloro-5-fluoro-1,1′-biphenyl-2-yl)-3-
(23-1) 2-butoxy-6-iodo-3-



(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide
propylbenzopyran-4-one


T-2
(1-1) N-(3′,4′-dichloro-5-fluoro-1,1′-biphenyl-2-yl)-3-
(23-2) 2-ethoxy-6-iodo-3-



(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide
propylbenzopyran-4-one


T-3
(1-7) N-(4′-bromo-1,1′-biphenyl-2-yl)-4-(difluoromethyl)-
(23-1) 2-butoxy-6-iodo-3-



2-methyl-1,3-thiazole-5-carboxamide
propylbenzopyran-4-one


T-4
(1-7) N-(4′-bromo-1,1′-biphenyl-2-yl)-4-(difluoromethyl)-
(23-2) 2-ethoxy-6-iodo-3-



2-methyl-1,3-thiazole-5-carboxamide
propylbenzopyran-4-one


T-5
(1-8) 4-(difluoromethyl)-2-methyl-N[4′-(trifluoromethyl)-1,1′-
(23-1) 2-butoxy-6-iodo-3-



biphenyl-2-yl]-1,3-thiazole-5-carboxamide
propylbenzopyran-4-one


T-6
(1-8) 4-(difluoromethyl)-2-methyl-N-[4′-(trifluoromethyl)-1,1′-
(23-2) 2-ethoxy-6-iodo-3-



biphenyl-2-yl]-1,3-thiazole-5-carboxamide
propylbenzopyran-4-one


T-7
(1-9) N-(4′-chloro-3′-fluoro-1,1′-biphenyl-2-yl)-4-(difluoro-
(23-1) 2-butoxy-6-iodo-3-



methyl)-2-methyl-1,3-thiazole-5-carboxamide
propylbenzopyran-4-one


T-8
(1-9) N-(4′-chloro-3′-fluoro-1,1′-biphenyl-2-yl)-4-(difluoro-
(23-2) 2-ethoxy-6-iodo-3-



methyl)-2-methyl-1,3-thiazole-5-carboxamide
propylbenzopyran-4-one









In addition to an active compound of the formula (I), the active compound combinations according to the invention comprise at least one active compound from the compounds of groups (2) to (23). In addition, they may also comprise further fungicidally active additives.


If the active compounds in the active compound combinations according to the invention are present in certain weight ratios, the synergistic effect is particularly pronounced. However, the weight ratios 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 (I) and a mixing partner from one of the groups (2) to (23) in the mixing ratios listed in an exemplary manner in Table 21 below.


The mixing ratios are based on ratios by weight. The ratio is to be understood as active compound of the formula (I): mixing partner.









TABLE 21







Mixing ratios











Particularly



Preferred
preferred


Mixing partner
mixing ratio
mixing ratio





Group (2): strobilurins
50:1 to 1:50
10:1 to 1:20


Group (3): triazoles except
50:1 to 1:50
20:1 to 1:20


for (3-15)




(3-15): prothioconazole
50:1 to 1:50
10:1 to 1:20


Group (4): sulphenamides
1:1 to 1:150
1:1 to 1:100


Group (5): valinamides
50:1 to 1:50
10:1 to 1:20


Group (6): carboxamides
50:1 to 1:50
20:1 to 1:20


Group (7): dithiocarbamates
1:1 to 1:150
1:1 to 1:100


Group (8): acylalanines
10:1 to 1:150
5:1 to 1:100


Group (9): anilinopyrimidines
5:1 to 1:50
1:1 to 1:20


Group (10): benzimidazoles
10:1 to 1:50
5:1 to 1:20


Group (11): carbamates
1:1 to 1:150
1:1 to 1:100


except for (11-1)




(11-1): diethofencarb
50:1 to 1:50
10:1 to 1:20


Group (12): (12-1)/(12-2)/(12-3)
1:1 to 1:150
1:5 to 1:100


Group (12): (12-4)/(12-5)/(12-6)
5:1 to 1:50
1:1 to 1:20


Group (13): guanidines
100:1 to 1:150
20:1 to 1:100


Group (14): imidazoles
50:1 to 1:50
10:1 to 1:20


Group (15): morpholines
50:1 to 1:50
10:1 to 1:20


Group (16): pyrroles
50:1 to 1:50
10:1 to 1:20


Group (17): phosphonates
10:1 to 1:150
1:1 to 1:100


Group (18): phenylethanamides
50:1 to 1:50
10:1 to 1:20


(19-1): acibenzolar-S-methyl
50:1 to 1:50
20:1 to 1:20


(19-2): chlorothalonil
1:1 to 1:150
1:1 to 1:100


(19-3): cymoxanil
10:1 to 1:50
5:1 to 1:20


(19-4): edifenphos
10:1 to 1:50
5:1 to 1:20


(19-5): famoxadone
50:1 to 1:50
10:1 to 1:20


(19-6): fluazinam
50:1 to 1:50
10:1 to 1:20


(19-7): copper oxychloride
1:1 to 1:150
1:5 to 1:100


(19-8): copper hydroxide
1:1 to 1:150
1:5 to 1:100


(19-9): oxadixyl
10:1 to 1:150
5:1 to 1:100


(19-10): spiroxamine
50:1 to 1:50
10:1 to 1:20


(19-11) dithianon
50:1 to 1:50
10:1 to 1:20


(19-12) metrafenone
50:1 to 1:50
10:1 to 1:20


(19-13) fenamidone
50:1 to 1:50
10:1 to 1:20


(19-14): 2,3-dibutyl-6-chlorothieno-
50:1 to 1:50
10:1 to 1:20


[2,3-d]pyrimidin-4(3H)one




(19-15): probenazole
10:1 to 1:150
5:1 to 1:100


(19-16): isoprothiolane
10:1 to 1:150
5:1 to 1:100


(19-17): kasugamycin
50:1 to 1:50
10:1 to 1:20


(19-18): phthalide
10:1 to 1:150
5:1 to 1:100


(19-19): ferimzone
50:1 to 1:50
10:1 to 1:20


(19-20): tricyclazole
50:1 to 1:50
10:1 to 1:20


(19-21): N-({4-[(cyclopropylamino)-
10:1 to 1:150
5:1 to 1:100


carbonyl]phenyl}sulphonyl)-2-




methoxybenzamide




(19-22) 2-(4-chlorophenyl)-N-{2-[3-
50:1 to 1:50
10:1 to 1:20


methoxy-4-(prop-2-yn-1-yloxy)-




phenyl]ethyl}-2-(prop-2-yn-1-




yloxy)acetamide




Group (20): (thio)urea derivatives
50:1 to 1:50
10:1 to 1:20


Group (21): amides
50:1 to 1:50
10:1 to 1:20


Group (22): triazolopyrimidines
50:1 to 1:50
10:1 to 1:20


Group (23): iodochromones
50:1 to 1:50
10:1 to 1:20









In each case, the mixing ratio is to be chosen such that a synergistic mixture is obtained. The mixing ratios between the compound of the formula (I) and a compound of one of the groups (2) to (23) may also vary between the individual compounds of a group.


The active compound combinations according to the invention have very good fungicidal properties and are suitable for controlling phytopathogenic fungi, such as Plasmodiophoromycetes, Oomycetes, Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes, Deuteromycetes, etc.


The active compound combinations according to the invention are particularly suitable for controlling Erysiphe graminis, Pyrenophora teres and Leptosphaeria nodorum.


Some pathogens causing fungal diseases which come under the generic names listed above may be mentioned by way of example, but not by way of limitation:



Pythium species, such as, for example, Pythium ultimum; Phytophthora species, such as, for example, Phytophthora infestans; Pseudoperonospora species, such as, for example, Pseudoperonospora humuli or Pseudoperonospora cubensis; Plasmopara species, such as, for example, Plasmopara viticola; Bremia species, such as, for example, Bremia lactucae; Peronospora species, such as, for example, Peronospora pisi or P. brassicae; Erysiphe species, such as, for example, Erysiphe graminis; Sphaerotheca species, such as, for example, Sphaerotheca fuliginea; Podosphaera species, such as, for example, Podosphaera leucotricha; Venturia species, such as, for example, Venturia inaequalis; Pyrenophora species, such as, for example, Pyrenophora teres or P. graminea (conidia form: Drechslera, syn: Helminthosporium); Cochliobolus species, such as, for example, Cochliobolus sativus (conidia form: Drechslera, syn: Helminthosporium); Uromyces species, such as, for example, Uromyces appendiculatus; Puccinia species, such as, for example, Puccinia recondita; Sclerotinia species, such as, for example, Sclerotinia sclerotiorum; Tilletia species, such as, for example, Tilletia caries; Ustilago species, such as, for example, Ustilago nuda or Ustilago avenae; Pellicularia species, such as, for example, Pellicularia sasakii; Pyricularia species, such as, for example, Pyricularia oryzae; Fusarium species, such as, for example, Fusarium culmorum; Botrytis species, such as, for example, Botrytis cinerea; Septoria species, such as, for example, Septoria nodorum; Leptosphaeria species, such as, for example, Leptosphaeria nodorum; Cercospora species, such as, for example, Cercospora canescens; Alternaria species, such as, for example, Alternaria brassicae; Pseudocercosporella species, such as, for example, Pseudocercosporella herpotrichoides, Rhizoctonia species, such as, for example, Rhizoctonia solani.


The fact that the active compound combinations are well tolerated by plants at the concentrations 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 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.


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 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, 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 and, in the case of propagation material, in particular in the case of seeds, furthermore by one- or multilayer coating.


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 biological breeding, such as crossing or protoplast fusion, and parts thereof, are treated. In a further preferred embodiment, transgenic plants and plant cultivars obtained by genetic engineering, if 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.


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 according to the invention, 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 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 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 and particularly emphasized examples of such properties are a better defense 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 are 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 fruits and grapes), and particular emphasis is given to maize, soya beans, potatoes, cotton and oilseed rape. Traits that are emphasized in particular are increased defense of the plants against insects, by toxins formed in the plants, in particular those formed in the plants by the genetic material from Bacillus thuringiensis (for example by the genes CryIA(a), CryIA(b), CryIA(c), CryIIA, CryIIIA, CryIIIB2, 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 certain herbicidally active compounds, for example imidazolinones, sulphonylureas, glyphosates or phosphinotricin (for example the “PAT” gene). The genes which impart the desired traits in question can also be present in combinations 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 bean), KnockOut® (for example maize), StarLink® (for example maize), Bollgard® (cotton), Nucoton® (cotton) and NewLeaf® (potato). Examples of herbicide-tolerant plants which may be mentioned are maize varieties, cotton varieties and soya bean varieties which are sold under the trade names Roundup Ready® (tolerance to glyphosates, for example maize, cotton, soya bean), Liberty Link® (tolerance to phosphinotricin, for example oilseed rape), IMI® (tolerance to imidazolinones) and STS® (tolerance to sulphonylureas, for example maize). Herbicide-resistant plants (plants bred in a conventional manner for herbicide tolerance) 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.


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 substances impregnated with active compound and microencapsulations in polymeric substances and in coating compositions for seeds, and ULV cool and 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 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 alkylnaphthalenes, chlorinated aromatics or chlorinated aliphatic hydrocarbons such as chlorobenzenes, chloro-ethylenes or methylene chloride, aliphatic hydrocarbons such as cyclohexane or paraffins, for example petroleum fractions, mineral and vegetable oils, alcohols such as butanol or glycol and their ethers and 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 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, ground natural minerals such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, and ground synthetic 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, 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 methylcellulose.


Tackifiers such as carboxymethylcellulose, natural and synthetic polymers in the form of powders, granules or latices, 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 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 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.


The formulations for controlling unwanted phytopathogenic fungi generally comprise between 0.1 and 95% by weight of active compounds, preferably between 0.5 and 90%.


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, 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.


The active compound combinations according to the invention can, in commercial formulations and in 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 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 combinations are generally between 0.1 and 10 000 g/ha, preferably between 10 and 1000 g/ha. In the treatment of seeds, 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 combination are generally between 0.1 and 10 000 g/ha, 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.


A synergistic effect in 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.


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 1967, 15, 20-22):


If

  • X is the efficacy when employing active compound A at an application rate of m g/ha,
  • Y is the efficacy when employing active compound B at an application rate of n g/ha and
  • E is the efficacy when employing active compounds A and B at application rates of m and n g/ha,


    then






E
=

X
+
Y
-


X
×
Y

100






Here, the efficacy is determined in %. 0% means an efficacy which corresponds to that of the control, 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 must exceed the value calculated using the above formula for the expected efficacy (E).


The invention is illustrated by the examples below. However, the invention is not limited to the examples.







USE EXAMPLES

In the use examples shown below, in each case mixtures of the carboxamides of the general formula (I) (group 1) below with the mixing partners given in each case (structural formulae see above) were tested.


Carboxamides of the formula (I) used:




embedded image


Example A


Pyrenophora teres Test (Barley)/Curative




  • Solvent: 50 parts by weight of N,N-dimethylacetamide

  • Emulsifier: 1 part by weight of alkylaryl polyglycol ether



To produce a suitable preparation of active compound, 1 part by weight of active compound or active compound combination is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration.


To test for curative activity, young plants are sprayed with a conidia suspension of Pyrenophora teres. The plants remain in an incubation cabinet at 20° C. and 100% relative atmospheric humidity for 48 hours. The plants are then sprayed with the preparation of active compound at the stated application rate.


The plants are placed in a greenhouse at a temperature of about 20° C. and a relative atmospheric humidity of about 80%.


Evaluation is carried out 12 days after the inoculation. 0% means an efficacy which corresponds to that of the control, whereas an efficacy of 100% means that no infection is observed.


The table below clearly shows that the activity found for the active compound combination according to the invention is higher than the calculated activity, i.e. that a synergistic effect is present.









TABLE A








Pyrenophora teres test (barley)/curative












Application rate of












active compound
Efficacy in %










Active compounds
in g/ha
found*
calc.**













(1-1)
25
43



(2-2) fluoxastrobin
25
0



(3-17) tebuconazole
25
29



(1-1) + (2-2) fluoxastrobin (1:1)
25 + 25
71
43


(1-1) + (3-17) tebuconazole (1:1)
25 + 25
71
60





*found = activity found


**calc. = activity calculated using Colby's formula






Example B


Erysiphe Test (Barley)/Protective




  • Solvent: 50 parts by weight of N,N-dimethylacetamide

  • Emulsifier: 1 part by weight of alkylaryl polyglycol ether



To produce a suitable preparation of active compound, 1 part by weight of active compound or active compound combination is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration.


To test for protective activity, young plants are sprayed with the preparation of active compound at the stated application rate. After the spray coating has dried on, the plants are dusted with spores of Erysiphe graminis f.sp. hordei.


Plants are placed in a greenhouse at a temperature of about 20° C. and a relative atmospheric humidity of about 80% to promote the development of mildew pustules.


Evaluation is carried out 6 days after the inoculation. 0% means an efficacy which corresponds to that of the control, whereas an efficacy of 100% means that no infection is observed.


The table below clearly shows that the activity found for the active compound combination according to the invention is higher than the calculated activity, i.e. that a synergistic effect is present.









TABLE B








Erysiphe test (barley)/protective











Application rate of




active compound
Efficacy in %










Active compounds
in g/ha
found*
calc.**













(1-1)
12.5
0



(2-4) trifloxystrobin
12.5
78



(3-15) prothioconazole
12.5
67



(1-1) + (2-4) trifloxystrobin (1:1)
12.5 + 12.5
94
78


(1-1) + (3-15) prothioconazole (1:1)
12.5 + 12.5
89
67





*found = activity found


**calc. = activity calculated using Colby's formula






Example C


Puccinia Test (Wheat)/Curative




  • Solvent: 50 parts by weight of N,N-dimethylacetamide

  • Emulsifier: 1 part by weight of alkylaryl polyglycol ether



To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration.


To test for curative activity, young plants are sprayed with a conidia suspension of Puccinia recondita. The plants remain in an incubation cabinet at 20° C. and 100% relative atmospheric humidity for 48 hours.


The plants are then sprayed with the preparation of active compound at the stated application rate.


The plants are placed in a greenhouse at a temperature of about 20° C. and a relative atmospheric humidity of about 80% to promote the development of rust pustules.


Evaluation is carried out 8 days after the inoculation. 0% means an efficacy which corresponds to that of the control, whereas an efficacy of 100% means that no infection is observed.


The table below clearly shows that the activity found for the active compound combination according to the invention is higher than the calculated activity, i.e. that a synergistic effect is present.









TABLE C








Puccinia test (wheat)/curative











Application rate of




active compound
Efficacy in %










Active compounds
in g/ha
found*
calc.**













(1-1)
62.5
22



(19-10) spiroxamine
62.5
0



(6-14)
62.5
44



(6-11)
62.5
0



(2-11) picoxystrobin
62.5
78



(1-1) + (19-10) spiroxamine (1:1)
62.5 + 62.5
100
22


(1-1) + (6-14) (1:1)
62.5 + 62.5
67
57


(1-1) + (6-11) (1:1)
62.5 + 62.5
44
22


(1-1) + (2-11) picoxystrobin (1:1)
62.5 + 62.5
89
83





*found = activity found


**calc. = activity calculated using Colby's formula






Example D


Gibberella zeae Test (Barley)/Curative




  • Solvent: 50 parts by weight of N,N-dimethylacetamide

  • Emulsifier: 1 part by weight of alkylaryl polyglycol ether



To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration.


To test for curative activity, young plants are sprayed with a conidia suspension of Gibberella zeae. The plants remain in an incubation cabinet at 22° C. and 100% relative atmospheric humidity for 24 hours. The plants are then sprayed with the preparation of active compound at the stated application rate. After the spray coating has dried on, the plants remain in a greenhouse under translucent incubation hoods at a temperature of about 22° C. and a relative atmospheric humidity of about 100%.


Evaluation is carried out 6 days after the inoculation. 0% means an efficacy which corresponds to that of the control, whereas an efficacy of 100% means that no infection is observed.


The table below shows clearly that the activity found for the active compound combination according to the invention is higher than the calculated activity, i.e. that a synergistic effect is present.









TABLE D








Gibberella zeae test (barley)/curative











Application rate of




active compound
Efficacy in %










Active compounds
in g/ha
found*
calc.**













(1-1)
62.5
40



(2-12) pyraclostrobin
62.5
80



(3-12) epoxyconazole
62.5
0



(1-1) + (2-12) pyraclostrobin (1:1)
62.5 + 62.5
90
88


(1-1) + (3-12) epoxyconazole (1:1)
62.5 + 62.5
60
40





*found = activity found


**calc. = activity calculated using Colby's formula






Example E


Sphaerotheca fuliginea Test (Cucumber)/Protective




  • Solvents: 24.5 parts by weight of acetone
    • 24.5 parts by weight of dimethylacetamide

  • Emulsifier: 1 part by weight of alkylaryl polyglycol ether



To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amounts of solvents and emulsifier, and the concentrate is diluted with water to the desired concentration.


To test for protective activity, young plants are sprayed with the preparation of active compound at the stated application rate. After the spray coating has dried on, the plants are inoculated with an aqueous spore suspension of Sphaerotheca fuliginea.


The plants are then placed in a greenhouse at about 23° C. and a relative atmospheric humidity of about 70%.


Evaluation is carried out 7 days after the inoculation. 0% means an efficacy which corresponds to that of the control, whereas an efficacy of 100% means that no infection is observed.


The table below clearly shows that the activity found for the active compound combination according to the invention is higher than the calculated activity, i.e. that a synergistic effect is present.









TABLE E








Sphaerotheca fuliginea test (cucumber)/protective











Application rate of




active compound
Efficacy in %










Active compounds
in g/ha
found*
calc.**













(1-1)
 4
30




 2
36




 1
16




 0.5
0



(1-7)
 2
0




 1
0




 0.5
0



(2-1) azoxystrobin
 0.5
20



(2-2) fluoxastrobin
 1
0



(2-4) trifloxystrobin
 2
10



(2-12) pyraclostrobin
 2
0



(3-15) prothioconazole
 1
43



(3-17) tebuconazole
 1
10



(3-21) bitertanol
 1
0



(4-2) tolylfluanid
20
0



(6-6) fenhexamid
20
0



(6-14) penthiopyrad
 4
0



(7-1) mancozeb
20
0



(7-4) propineb
20
11



(9-3) pyrimethanil
20
0



(12-4) iprodione
20
0



(19-2) chlorothalonil
20
0



(19-10) spiroxamine
20
0



(22-1)
 2
11



(22-2)
 1
22



(1-1) + (2-1) azoxystrobin (1:1)
0.5 + 0.5
87
20


(1-7) + (2-1) azoxystrobin (1:1)
0.5 + 0.5
63
20


(1-1) + (2-2) fluoxastrobin (1:1)
  1 + 1
95
16


(1-7) + (2-2) fluoxastrobin (1:1)
  1 + 1
92
0


(1-1) + (2-4) trifloxystrobin (1:1)
  2 + 2
57
42


(1-7) + (2-4) trifloxystrobin (1:1)
  2 + 2
93
10


(1-1) + (2-12) pyraclostrobin (1:1)
  2 + 2
53
36


(1-1) + (3-15) prothioconazole (1:1)
  1 + 1
70
52


(1-1) + (3-17) tebuconazole (1:1)
  1 + 1
90
24


(1-1) + (3-21) bitertanol (1:1)
  1 + 1
50
16


(1-1) + (4-2) tolylfluanid (1:10)
  2 + 20
98
36


(1-1) + (6-6) fenhexamid (1:10)
  2 + 20
85
36


(1-1) + (6-14) penthiopyrad (1:1)
  4 + 4
82
30


(1-1) + (7-1) mancozeb (1:10)
  2 + 20
93
36


(1-1) + (7-4) propineb (1:10)
  2 + 20
65
43


(1-1) + (9-3) pyrimethanil (1:10)
  2 + 20
96
36


(1-1) + (12-4) iprodione (1:10)
  2 + 20
74
36


(1-1) + (19-2) chlorothalonil (1:10)
  2 + 20
91
36


(1-1) + (19-10) spiroxamine (1:10)
  2 + 20
100
36


(1-1) + (22-1) (1:1)
  2 + 2
67
43


(1-1) + (22-2) (1:1)
  1 + 1
94
34





*found = activity found


**calc. = activity calculated using Colby's formula






Example F


Alternaria solani Test (Tomato)/Protective




  • Solvents: 24.5 parts by weight of acetone
    • 24.5 parts by weight of dimethylacetamide

  • Emulsifier: 1 part by weight of alkylaryl polyglycol ether



To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amounts of solvents and emulsifier, and the concentrate is diluted with water to the desired concentration.


To test for protective activity, young plants are sprayed with the preparation of active compound at the stated application rate. After the spray coating has dried on, the plants are inoculated with an aqueous spore suspension of Alternaria solani.


The plants are then placed in an incubation cabinet at about 20° C. and 100% relative atmospheric humidity.


Evaluation is carried out 3 days after the inoculation. 0% means an efficacy which corresponds to that of the control, whereas an efficacy of 100% means that no infection is observed.


The table below clearly shows that the activity found for the active compound combination according to the invention is higher than the calculated activity, i.e. that a synergistic effect is present.









TABLE F








Alternaria solani test (tomato)/protective











Application rate of




active compound
Efficacy in %










Active compounds
in g/ha
found*
calc.**













(1-1)
1
61




0.5
42



(1-7)
1
63




0.5
28



(2-3)
0.5
22



(3-3) propiconazole
0.5
3



(5-3) benthiavalicarb
1
5



(8-4) metalaxyl-M
0.5
7



(8-5) benalaxyl-M
0.5
14



(1-7) + (2-3) (1:1)
0.5 + 0.5
67
44


(1-7) + (3-3) propiconazole (1:1)
0.5 + 0.5
56
30


(1-1) + (5-3) benthiavalicarb (1:1)
  1 + 1  
77
63


(1-1) + (8-4) metalaxyl-M (1:1)
0.5 + 0.5
62
46


(1-1) + (8-5) benalaxyl-M (1:1)
0.5 + 0.5
67
50





*found = activity found


**calc. = activity calculated using Colby's formula






Example G


Phytophthora infestans Test (Tomato)/Protective




  • Solvents: 24.5 parts by weight of acetone
    • 24.5 parts by weight of dimethylacetamide

  • Emulsifier: 1 part by weight of alkylaryl polyglycol ether



To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amounts of solvents and emulsifier, and the concentrate is diluted with water to the desired concentration.


To test for protective activity, young plants are sprayed with the preparation of active compound at the stated application rate. After the spray coating has dried on, the plants are inoculated with an aqueous spore suspension of Phytophthora infestans. The plants are then placed in an incubation cabinet at about 20° C. and 100% relative atmospheric humidity.


Evaluation is carried out 3 days after the inoculation. 0% means an efficacy which corresponds to that of the control, whereas an efficacy of 100% means that no infection is observed.


The table below clearly shows that the activity found for the active compound combination according to the invention is higher than the calculated activity, i.e. that a synergistic effect is present.









TABLE G








Phytophthora infestans test (tomato)/protective











Application rate of




active compound
Efficacy in %










Active compounds
in g/ha
found*
calc.**













(1-1)
10
0




5
0




1
0




0.5
0



(4-2) tolylfluanid
10
0



(5-1) iprovalicarb
10
64




5
61



(5-3) benthiavalicarb
0.5
56



(19-13) fenamidone
0.5
41



(1-1) + (4-2) tolylfluanid (1:10)
  1 + 10 
51
0


(1-1) + (5-1) iprovalicarb (1:1)
 10 + 10 
88
64



  5 + 5  
77
61


(1-1) + (5-3) benthiavalicarb (1:1)
0.5 + 0.5
73
56


(1-1) + (19-13) fenamidone (1:1)
0.5 + 0.5
51
41





*found = activity found


**calc. = activity calculated using Colby's formula






Example H


Botrytis cinerea Test (Bean)/Protective




  • Solvents: 24.5 parts by weight of acetone
    • 24.5 parts by weight of dimethylacetamide

  • Emulsifier: 1 part by weight of alkylaryl polyglycol ether



To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amounts of solvents and emulsifier, and the concentrate is diluted with water to the desired concentration.


To test for protective activity, young plants are sprayed with the preparation of active compound at the stated application rate. After the spray coating has dried on, 2 small pieces of agar colonized by Botrytis cinerea are placed onto each leaf. The inoculated plants are placed in a darkened chamber at about 20° C. and 100% relative atmospheric humidity.


The size of the infected areas on the leaves is evaluated 2 days after the inoculation. 0% means an efficacy which corresponds to that of the control, whereas an efficacy of 100% means that no infection is observed.


The table below clearly shows that the activity found for the active compound combination according to the invention is higher than the calculated activity, i.e. that a synergistic effect is present.









TABLE H








Botrytis cinerea test (bean)/protective











Application rate of




active compound
Efficacy in %










Active compounds
in g/ha
found*
calc.**













(1-1)
5
54



(9-3) pyrimethanil
5
4



(12-4) iprodione
5
13



(1-1) + (9-3) pyrimethanil (1:1)
5 + 5
92
56


(1-1) + (12-4) iprodione (1:1)
5 + 5
100
60





*found = activity found


**calc. = activity calculated using Colby's formula






Example I


Alternaria mali Test (In Vitro)/Microtitre Plates


The microtest 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.


For inoculation, a spore suspension of Alternaria mali is used. After 5 days of incubation in the dark and with shaking (10 Hz), for each filled cavity of the microtitre plates, the light transmittance 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.


The table below clearly shows that the activity found for the active compound combination according to the invention is higher than the calculated activity, i.e. that a synergistic effect is present.









TABLE I








Alternaria mali test (in vitro)/microtitre plates











Application rate of




active compound
Efficacy in %










Active compounds
in ppm
found*
calc.**













(1-1)
0.03
51




0.003
25



(10-3) carbendazim
0.03
15



(19-3) fenamidone
0.003
2



(20-1) pencycuron
0.003
11



(1-1) + (10-3) carbendazim (1:1)
 0.03 + 0.03 
79
59


(1-1) + (19-3) fenamidone (1:1)
0.003 + 0.003
35
27


(1-1) + (20-1) pencycuron (1:1)
0.003 + 0.003
67
33





*found = activity found


**calc. = activity calculated using Colby's formula






Example J


Rhizoctonia solani Test (In Vitro)/Microtitre Plates


The microtest 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.


For inoculation, a mycelium suspension of Rhizoctonia solani is used. After 5 days of incubation in the dark and with shaking (10 Hz), for each filled cavity of the microtitre plates, the light transmittance 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.


The table below clearly shows that the activity found for the active compound combination according to the invention is higher than the calculated activity, i.e. that a synergistic effect is present.









TABLE J








Rhizoctonia solani test (in vitro)/microtitre plates











Application rate of




active compound
Efficacy in %










Active compounds
in ppm
found*
calc.**





(1-1)
0.3
80




0.1
40



(17-1) fosetyl-A1
0.3
24



(11-2) propamocarb
0.1
25



(1-1) + (17-1) fosetyl-A1 (1:1)
0.3 + 0.3
98
85


(1-1) + (11-2) propamocarb (1:1)
0.1 + 0.1
88
55





*found = activity found


**calc. = activity calculated using Colby's formula






Example K


Septoria tritici Test (In Vitro)/Microtitre Plates


The microtest 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.


For inoculation, a spore suspension of Septoria tritici is used. After 7 days of incubation in the dark and with shaking (10 Hz), for each filled cavity of the microtitre plates, the light transmittance 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.


The table below clearly shows that the activity found for the active compound combination according to the invention is higher than the calculated activity, i.e. that a synergistic effect is present.









TABLE K








Septoria tritici test (in vitro)/microtitre plates











Application rate of




active compound
Efficacy in %










Active compounds
in ppm
found*
calc.**





(1-1)
0.01
15



(14-3) triazoxide
0.01
29



(1-1) + (14-3) triazoxide (1:1)
0.01 + 0.01
69
40





*found = activity found


**calc. = activity calculated using Colby's formula






Example L


Sphaerotheca fuliginea Test (Gherkin)/Protective


To produce a suitable preparation of active compound, the substance to be tested is homogenized in a mixture of acetone/Tween/water. The suspension is then diluted with water to the desired concentration.


Gherkin plants (Vert petit de Paris cultivar) are sown in starter cups on 50/50 peat soil/pozzolana soil substrate and cultivated at 20° C./23° C. At the 2-leaf stage, the plants are sprayed with the preparation of active compound at the stated application rate.


To test for protective activity, the plants are, after 24 h, sprayed with an aqueous spore suspension of Sphaerotheca fuliginea (100 000 spores/ml). The plants then remain at 20° C./25° C. and 60/70% relative atmospheric humidity.


Evaluation is carried out 21 days after the inoculation. 0% means an efficacy which corresponds to that of the control, whereas an efficacy of 100% means that no infection is observed.


The table below shows clearly that the activity found for the active compound combination according to the invention is higher than the calculated activity, i.e. that a synergistic effect is present.









TABLE L








Sphaerotheca fuliginea test (gherkin)/protective











Application rate of




active compound
Efficacy in %










Active compounds
in ppm
found*
calc.**





(1-1)
8
60



(6-2) boscalid
8
50



(1-1) + (6-2) boscalid (1:1)
8 + 8
98
80





*found = activity found


**calc. = activity calculated using Colby's formula





Claims
  • 1. A composition comprising (1-1) N-(3′,4′-dichloro-5-fluoro-1,1′-biphenyl-2-yl)-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide and at least one fungicidal compound selected from the group consisting of: (19-2) chlorothalonil; (19-10) spiroxamine; and (19-13) fenamidone wherein the weight ratio of (1-1) to (19-2), (19-10) or (19-13) is from 1:1 to 1:20, and wherein if the fungicidal compound is spiroxamine, then spiroxamine and N-(3′,4′-dichloro-5-fluoro-1,1′-biphenyl-2-yl)-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide are the only fungicidal compounds in the composition.
  • 2. A method for controlling unwanted phytopathogenic fungi, comprising applying a composition according to claim 1 to the unwanted phytopathogenic fungi, their habitat, or a combination thereof.
  • 3. A process for preparing a fungicidal composition, comprising mixing a composition according to claim 1 with an extender, a surfactant, or a combination thereof.
  • 4. The composition of claim 1 wherein the active compound is spiroxamine.
  • 5. The composition of claim 1, which comprises (1-1) N-(3′,4′-dichloro-5-fluoro-1,1′-biphenyl-2-yl)-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide and (19-2) chlorothalonil.
  • 6. The composition of claim 1, which comprises (1-1) N-(3′,4′-dichloro-5-fluoro-1,1′-biphenyl-2-yl)-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide and (19-13) fenamidone.
Priority Claims (1)
Number Date Country Kind
103-47-090 Oct 2003 DE national
US Referenced Citations (155)
Number Name Date Kind
1972961 Tisdale et al. Sep 1934 A
2504404 Flenner Apr 1950 A
2553770 Kittleson et al. May 1951 A
2588428 Stewart et al. Mar 1952 A
3010968 Loux Nov 1961 A
3178447 Kohn Apr 1965 A
3206468 Grenda Sep 1965 A
3248400 Flieg et al. Apr 1966 A
3249499 von Schmeling et al. May 1966 A
3285929 Klauke et al. Nov 1966 A
3290353 Battershell et al. Dec 1966 A
3379610 Lyon et al. Apr 1968 A
3499951 Schrader et al. Mar 1970 A
3513241 Hoyer et al. May 1970 A
3546813 Frohberger et al. Dec 1970 A
3629428 Seki et al. Dec 1971 A
3631176 Klopping Dec 1971 A
3745170 Fujinami et al. Jul 1973 A
3745187 Noguchi et al. Jul 1973 A
3755350 Sauli Aug 1973 A
3856814 Taninaka et al. Dec 1974 A
3912752 Meiser et al. Oct 1975 A
3952002 Kramer et al. Apr 1976 A
3966750 Mangold et al. Jun 1976 A
3991071 Brookes et al. Nov 1976 A
4046911 Hubele Sep 1977 A
4064261 Paget Dec 1977 A
4068077 Goetz et al. Jan 1978 A
4079062 Van Reet et al. Mar 1978 A
4127673 Yamada et al. Nov 1978 A
4139616 Ducret et al. Feb 1979 A
4239760 Sasse et al. Dec 1980 A
4291049 Bosone et al. Sep 1981 A
4294850 Hubele Oct 1981 A
4432989 Spencer Feb 1984 A
4532341 Holmwood et al. Jul 1985 A
4598085 Heeres et al. Jul 1986 A
4664696 Schaub May 1987 A
4705800 Nyfeler et al. Nov 1987 A
4829085 Wenderoth et al. May 1989 A
4851405 Krámer et al. Jul 1989 A
4906652 Karbach et al. Mar 1990 A
4910200 Curtze et al. Mar 1990 A
4931560 Hubele Jun 1990 A
4931581 Schurter et al. Jun 1990 A
4988734 Kraatz et al. Jan 1991 A
5059623 Krüger et al. Oct 1991 A
5087635 Shaber Feb 1992 A
5112849 Staub et al. May 1992 A
5256683 Hutt et al. Oct 1993 A
5266585 Hubele et al. Nov 1993 A
5330995 Eicken et al. Jul 1994 A
5334607 Sauter et al. Aug 1994 A
5438070 Eicken et al. Aug 1995 A
5453531 Seitz et al. Sep 1995 A
5593996 Pees et al. Jan 1997 A
5599828 Zeun et al. Feb 1997 A
5650519 Lacroix et al. Jul 1997 A
5679676 Krüger et al. Oct 1997 A
5789428 Shibata et al. Aug 1998 A
5789430 Jautelat et al. Aug 1998 A
5859039 Jautelat et al. Jan 1999 A
5869517 Müller et al. Feb 1999 A
5948932 Grote et al. Sep 1999 A
5986135 Pfrengle et al. Nov 1999 A
5998450 Eicken et al. Dec 1999 A
5998455 Knauf-Beiter et al. Dec 1999 A
6020354 Assmann et al. Feb 2000 A
6103717 Heinemann et al. Aug 2000 A
6114362 Dutzmann et al. Sep 2000 A
6130224 Eicken et al. Oct 2000 A
6143745 Eicken et al. Nov 2000 A
6159992 Müller et al. Dec 2000 A
6169056 Bayer et al. Jan 2001 B1
6191128 Stenzel et al. Feb 2001 B1
6235743 Gayer et al. May 2001 B1
6277791 Assmann et al. Aug 2001 B1
6297263 Dutzmann et al. Oct 2001 B1
6306414 Koike Oct 2001 B1
6306850 Dutzmann et al. Oct 2001 B1
6346538 Schelberger et al. Feb 2002 B1
6350765 Schelberger et al. Feb 2002 B1
6355634 Isenring et al. Mar 2002 B1
6372748 Schelberger et al. Apr 2002 B1
6407100 Isenring et al. Jun 2002 B1
6423726 Dutzmann et al. Jul 2002 B2
6479542 Sembo et al. Nov 2002 B2
6559136 Mauler-Machnik et al. May 2003 B1
6602823 Röchling et al. Aug 2003 B1
7008903 Dutzmann et al. Mar 2006 B2
7329633 Dunkel et al. Feb 2008 B2
7358214 Dunkel et al. Apr 2008 B2
7521397 Dunkel et al. Apr 2009 B2
7538073 Elbe et al. May 2009 B2
7655599 Röchling et al. Feb 2010 B2
7799739 Dunkel et al. Sep 2010 B2
7820708 Dunkel et al. Oct 2010 B2
7879760 Dunkel et al. Feb 2011 B2
8415274 Wachendorff-Neumann et al. Apr 2013 B2
8486858 Seitz et al. Jul 2013 B2
8652997 Assmann et al. Feb 2014 B2
20020156108 Eicken et al. Oct 2002 A1
20020173529 Dutzmann et al. Nov 2002 A1
20020198222 Bruns et al. Dec 2002 A1
20040039043 Elbe et al. Feb 2004 A1
20040110771 Blasco et al. Jun 2004 A1
20050009703 Wachendorff-Neumann et al. Jan 2005 A1
20050009883 Uhr et al. Jan 2005 A1
20050101639 Ammermann et al. May 2005 A1
20050124815 Elbe et al. Jun 2005 A1
20050143428 Dunkel et al. Jun 2005 A1
20050165076 Ammermann et al. Jul 2005 A1
20060004070 Wachendorff-Neumann et al. Jan 2006 A1
20060014738 Wachendorff-Neumann et al. Jan 2006 A1
20060035942 Wachendorff-Neumann et al. Feb 2006 A1
20060079401 Dutzmann et al. Apr 2006 A1
20060116414 Dunkel et al. Jun 2006 A1
20060276342 Krahmer et al. Dec 2006 A1
20070004921 Dunkel et al. Jan 2007 A1
20070010399 Rosinger et al. Jan 2007 A1
20070037799 Dahmen et al. Feb 2007 A1
20070054804 Suty-Heinze Mar 2007 A1
20070078171 Andersch et al. Apr 2007 A1
20070142327 Funke et al. Jun 2007 A1
20070155797 Andersch et al. Jul 2007 A1
20070196406 Dunkel et al. Aug 2007 A1
20070203025 Bickers et al. Aug 2007 A1
20070213396 Thielert et al. Sep 2007 A1
20070232598 Funke et al. Oct 2007 A1
20070270416 Funke et al. Nov 2007 A1
20070293550 Röchling et al. Dec 2007 A1
20070298966 Fischer et al. Dec 2007 A1
20080027114 Funke et al. Jan 2008 A1
20080070863 Funke et al. Mar 2008 A1
20080255071 Suty-Heinze et al. Oct 2008 A1
20080261811 Krohn et al. Oct 2008 A1
20080269051 Suty-Heinze et al. Oct 2008 A1
20080269263 Dahmen et al. Oct 2008 A1
20080274882 Krohn et al. Nov 2008 A1
20090018015 Wachendorff-Neumann et al. Jan 2009 A1
20090069178 Suty-Heinze et al. Mar 2009 A1
20090069398 Dunkel et al. Mar 2009 A1
20090105311 Dunkel et al. Apr 2009 A1
20090118346 Dunkel et al. May 2009 A1
20090170912 Erdelen et al. Jul 2009 A1
20090170918 Wolf Jul 2009 A1
20090286681 Dahmen et al. Nov 2009 A1
20090306109 Dutzmann et al. Dec 2009 A1
20110033433 Davies et al. Feb 2011 A1
20110034496 Häuser-Hahn et al. Feb 2011 A1
20110110906 Andersch et al. May 2011 A1
20110124501 Cristau et al. May 2011 A1
20110152097 Stenzel et al. Jun 2011 A1
20120015910 Wachendorff-Neumann et al. Jan 2012 A1
20130197018 Wachendorff-Neumann et al. Aug 2013 A1
Foreign Referenced Citations (126)
Number Date Country
7726387 Feb 1988 AU
610 079 May 1991 AU
2 476 462 Apr 2011 CA
1 076 434 Feb 1960 DE
1 081 446 May 1960 DE
1 193 498 May 1965 DE
1 209 799 Jan 1966 DE
1 234 704 Feb 1967 DE
1 493 736 Apr 1969 DE
1 806 123 Jun 1969 DE
2 012 656 Sep 1971 DE
2 149 923 Apr 1972 DE
2 250 077 Apr 1973 DE
2 201 063 Jul 1973 DE
2 207 576 Aug 1973 DE
2 312 956 Sep 1973 DE
23 24 010 Jan 1975 DE
24 29 523 Jan 1975 DE
24 56 627 Jun 1975 DE
25 13 732 Oct 1975 DE
25 15 091 Oct 1975 DE
25 51 560 May 1976 DE
25 43 279 Apr 1977 DE
27 32 257 Jan 1978 DE
27 35 872 Feb 1978 DE
26 56 747 Jun 1978 DE
28 02 488 Jul 1979 DE
29 03 612 Aug 1979 DE
140 041 Feb 1980 DE
30 30 026 Mar 1981 DE
30 42 303 Aug 1981 DE
151 404 Oct 1981 DE
34 06 993 Sep 1984 DE
37 21 786 Jan 1988 DE
37 35 555 Sep 1988 DE
40 26 966 Feb 1992 DE
44 23 612 Jan 1996 DE
195 31 813 Mar 1997 DE
195 39 324 Apr 1997 DE
196 02 095 Jul 1997 DE
196 46 407 May 1998 DE
101 24 208 Nov 2002 DE
102 15 292 Aug 2003 DE
0 015 756 Sep 1980 EP
0 019 450 Nov 1980 EP
0 031 257 Jul 1981 EP
0 040 345 Nov 1981 EP
0 040 345 Nov 1981 EP
0 068 813 Jan 1983 EP
0 078 663 May 1983 EP
0 112 284 Jun 1984 EP
0 145 294 Jun 1985 EP
0 155 509 Sep 1985 EP
0 183 458 Jun 1986 EP
0 196 038 Oct 1986 EP
0 206 999 Dec 1986 EP
0 219 756 Apr 1987 EP
0 234 242 Sep 1987 EP
0 236 272 Sep 1987 EP
0 248 086 Dec 1987 EP
0 253 213 Jan 1988 EP
0 256 503 Feb 1988 EP
0 258 161 Mar 1988 EP
0 262 393 Apr 1988 EP
0 270 111 Jun 1988 EP
0 278 595 Aug 1988 EP
0 298 196 Jan 1989 EP
0 310 550 Apr 1989 EP
0 313 512 Apr 1989 EP
0 315 502 May 1989 EP
0 329 397 Aug 1989 EP
0 339 418 Nov 1989 EP
0 341 475 Nov 1989 EP
0 378 953 Jul 1990 EP
0 382 375 Aug 1990 EP
0 393 911 Oct 1990 EP
0 398 692 Nov 1990 EP
0 460 575 Dec 1991 EP
0 515 901 Dec 1992 EP
0 537 957 Apr 1993 EP
0 545 099 Jun 1993 EP
0 589 301 Mar 1994 EP
0 596 254 May 1994 EP
0 600 629 Jun 1994 EP
0 604 019 Jun 1994 EP
0 629 616 Dec 1994 EP
0 639 574 Feb 1995 EP
0 737 682 Oct 1996 EP
0 897 904 Feb 1999 EP
1 214 881 Jun 2002 EP
935981 Sep 1963 GB
988630 Apr 1965 GB
1094567 Dec 1967 GB
1103989 Feb 1968 GB
1114155 May 1968 GB
1 425 621 Feb 1976 GB
1 591 267 Jun 1981 GB
2 262 037 Jun 1993 GB
07-206608 Aug 1995 JP
WO 9213830 Aug 1992 WO
WO 9504728 Feb 1995 WO
WO 9601559 Jan 1996 WO
WO 9604252 Feb 1996 WO
WO 9616048 May 1996 WO
WO 9618631 Jun 1996 WO
WO 9623793 Aug 1996 WO
WO 9706171 Feb 1997 WO
WO 9708952 Mar 1997 WO
WO 9710716 Mar 1997 WO
WO 9739630 Oct 1997 WO
WO 9808385 Mar 1998 WO
WO 9823155 Jun 1998 WO
WO 9914202 Mar 1999 WO
WO 9924413 May 1999 WO
WO 9931980 Jul 1999 WO
WO 9931985 Jul 1999 WO
WO 9942447 Aug 1999 WO
WO 9963813 Dec 1999 WO
WO 0187822 Nov 2001 WO
WO 0208197 Jan 2002 WO
WO 0238542 May 2002 WO
WO 0238565 May 2002 WO
WO 03014103 Feb 2003 WO
WO 03066609 Aug 2003 WO
WO 03066610 Aug 2003 WO
WO 03070705 Aug 2003 WO
Non-Patent Literature Citations (51)
Entry
Colby, S.R., “Calculating Synergistic and Antagonistic Responses of Herbicide Combinations,” Weeds 15:20-22, Weed Society of America (1967).
“Dicholofluanid,” in The Pesticide Manual: A World Compendium, 9th edition, Worthing, C.E., ed., Hampshire, UK, p. 249(1991).
“Tolylfluanid,” in The Pesticide Manual: A World Compendium, 9th edition, Worthing, C.E., ed., Hampshire, UK, p. 827(1991).
Patent Abstracts of Japan, English language abstract for JP 07-206608 (listed on accompanying PTO/SB/08A as FP88), 1995.
STNEasy Database, Accession No. 1962:12696, English language abstract for DE 1 081 446 (listed on accompanying PTO/SB/08A as FP2).
STNEasy Database, Accession No. 1980:586371, English language abstract for DD 140 041 (listed on accompanying PTO/SB/08A as FP32).
STNEasy Database, Accession No. 1981:401897, English language abstract for DE 30 30 026 (listed on accompanying PTO/SB/08A as FP35).
STNEasy Database, Accession No. 1982:157395, English language abstract for DD 151 404 (listed on accompanying PTO/SB/08A as FP39).
STNEasy Database, Accession No. 1988:510440, English language abstract for EP 0 258 161 (listed on accompanying PTO/SB/08A as FP58).
International Search Report for International Application No. PCT/EP2004/010830, European Patent Office, Netherlands, completed Nov. 22, 2004.
Bauer, T.A., et al., “Response of Selected Weed Species to Postemergence Imazethapyr and Bentazon,” Weed Tech. 9:236-242, The Weed Science Society of America, United States (1995).
Blackshaw, R.E., “HOE-39866 Use in Chemical Fallow Systems,” Weed Tech. 3:420-428, The Weed Science Society of America, United States (1989).
Blackshaw, R.E., “Synergistic Mixes of DPX-A7881 and Clopyralid in Canola (Brassica napus),” Weed Tech. 3:690-695, The Weed Science Society of America, United States (1989).
Blackshaw, R.E., et al., “Herbicide Combinations for Postemergent Weed Control in Safflower (Carthamus tinctorius),” Weed Tech. 4:97-104, The Weed Science Society of America, United States (1990).
Blouin, D.C., et al., “Analysis of Synergistic and Antagonistic Effects of Herbicides Using Nonlinear Mixed-Model Methodology,” Weed Tech. 18:464-472, The Weed Science Society of America, United States (2004).
Bradley, P.R., et al., “Response of Sorghum (Sorghum bicolor) to Atrazine, Ammonium Sulfate, and Glyphosate,” Weed Tech. 14:15-18, The Weed Science Society of America, United States (2000).
Buker, III, R.S., et al., “Confirmation and Control of a Paraquat-Tolerant Goosegrass (Eleusine indica) Biotype,” Weed Tech. 16:309-313, The Weed Science Society of America, United States (2002).
Burke, I.C., et al., “CGA-362622 Antagonizes Annual Grass Control with Clethodim,” Weed Tech. 16:749-754, The Weed Science Society of America, United States (2002).
Flint, J.L., et al., “Analyzing Herbicide Interactions, A Statistical Treatment of Colby's Method,” Weed Tech. 2:304-309, The Weed Science Society of America, United States (1988).
Gillespie, G.R., and Nalewaja, J.D., “Wheat (Triticum aestivum) Response to Triallate Plus Chlorsulfuron,” Weed Tech. 3:20-23, The Weed Science Society of America, United States (1989).
Green, J.M., et al., “Metribuzin and Chlorimuron Mixtures for Preemergence Broadleaf Weed Control in Soybeans, Glycine max,” Weed Tech. 2:355-363, The Weed Science Society of America, United States (1988).
Harker, N.K., and O'Sullivan, P.A., “Synergistic Mixtures of Sethoxydim and Fluazifop on Annual Grass Weeds,” Weed Tech. 5:310-316, The Weed Science Society of America, United States (1991).
Kent, L.M., et al., “Effect of Ammonium Sulfate, Imazapyr, and Environment on the Phytotoxicity of Imazethapyr,” Weed Tech. 5:202-205, The Weed Science Society of America, United States (1991).
Kotoula-Syka, E., et al., “Interactions between SAN 582H and Selected Safeners on Grain Sorghum (Sorghum bicolor) and Corn (Zea mays),” Weed Tech. 10:299-304, The Weed Science Society of America, United States (1996).
Lanclos, D.Y., et al., “Glufosinate Tank-Mix Combinations in Glufosinate-Resistant Rice (Oryza sativa),” Weed Tech. 16:659-663, The Weed Science Society of America, United States (2002).
Norris, J.L., et al., “Weed Control from Herbicide Combinations with Three Formulations of Glyphosate,” Weed Tech. 15:552-558, The Weed Science Society of America, United States (2001).
Novosel, K.M., et al., “Metolachlor Efficacy as Influenced by Three Acetolactate Synthase-Inhibiting Herbicides,” Weed Tech. 12:248-253, The Weed Science Society of America, United States (1998).
Palmer, E.W., et al., “Broadleaf Weed Control in Soybean (Glycine max) with CGA-277476 and Four Postemergence Herbicides,” Weed Tech. 14:617-623, The Weed Science Society of America, United States (2000).
Salzman, F.P., and Renner, K.A., “Response of Soybean to Combinations of Clomazone, Metribuzin, Linuron, Alachlor, and Atrazine,” Weed Tech. 6:922-929, The Weed Science Society of America, United States (1992).
Scott, R.C., et al., “Spray Adjuvant, Formulation, and Environmental Effects on Synergism from Post-Applied Tank Mixtures of SAN 582H with Fluazifop-P, Imazethapyr, and Sethoxydim,” Weed Tech. 12:463-469, The Weed Science Society of America, United States (1998).
Shaw, D.R. and Arnold, J.C., “Weed Control from Herbicide Combinations with Glyphosate,” Weed Tech. 16:1-6, The Weed Science Society of America, United States (2002).
Snipes, C.E., and Allen, R.L., “Interaction of Graminicides Applied in Combination with Pyrithiobac,” Weed Tech. 10:889-892, The Weed Science Society of America, United States (1996).
Wehtje, G. and Walker, R.H., “Interaction of Glyphosate and 2,4-DB for the Control of Selected Morningglory (Ipomoea spp.) Species,” Weed Tech. 11:152-156, The Weed Science Society of America, United States (1997).
Zhang, W., et al., “Fenoxaprop Interactions for Barnyardgrass (Echinochloa crus-galli) Control in Rice,” Weed Tech. 19:293-297, The Weed Science Society of America, United States (2005).
Rummens, F.H.A., “An Improved Definition of Synergistic and Antagonistic Effects,” Weed Science 23(1):4-6, The Weed Science Society of America, United States (1975).
Prosecution History of European Patent Appl. No. 03735610.2 (European Counterpart of U.S. Appl. No. 10/518,742), Jul. 13, 2006-Sep. 25, 2009.
Partial English language translation of Prosecution History of European Patent Appl. No. 03735610.2, Jul. 13, 2006-Sep. 25, 2009.
Opposition Proceeding in European Patent No. EP-B-1482798, Mar. 5, 2007-Nov. 9, 2009.
Partial English language translation of Opposition Proceeding in European Patent No. EP-B-1482798, Feb. 26, 2007-Nov. 9, 2009.
Tomlin, C., ed, The Pesticide Manual, 1242-1245, British Crop Protection Council, Farnham, UK (1997).
“Metominostrobin data sheet,” Compendium of Pesticide Common Names, accessed at http://www.alanwood.net/pesticides/metominostrobin.html, accessed on Apr. 8, 2009, 1 page.
“Azoxystrobin data sheet,” Compendium of Pesticide Common Names, accessed at http://www.alanwood.net/pesticides/azoxystrobin.html, accessed on Apr. 8, 2009, 1 page.
NPL43 “Kresoxim-methyl data sheet,” Compendium of Pesticide Common Names, accessed at http://www.alanwood.net/pesticides/kresoxim-methyl.html, accessed on Apr. 8, 2009, 1 page.
Office Action dated Jan. 4, 2011, in U.S. Appl. No. 11/997,079, inventor Dahmen, P., filed Jul. 28, 2008.
Hirt, E.E., Office Action for U.S. Appl. No. 11/916,436, inventors: Dunkel et al., § 371(c) Date: Nov. 7, 2008, U.S. Patent and Trademark Office, Alexandria, Virginia, dated Jul. 18, 2011.
European Search Report and Written Opinion for European Patent Application No. 10 163 282.6, European Patent Office, Munich, Germany, dated Feb. 2, 2011.
Unverified English translation of text portion of European Search Report and Written Opinion for European Patent Application No. 10 163 282.6, European Patent Office, Munich, Germany, dated Feb. 2, 2011.
Unverified English translation of claims of corresponding European Patent Application No. 10 163 282.6, filed Sep. 28, 2004, European Patent Office, Munich, Germany.
Hirt, E.E., Office Action for U.S. Appl. No. 11/916,436, Inventors: Dunkel et al., § 371(c) Date: Nov. 7, 2008, U.S. Patent and Trademark Office, Alexandria, Virginia, dated Jan. 30, 2012.
Holt, A.M., Office Action for U.S. Appl. No. 13/100,464, Inventors: Dahmen et al., filed May 4, 2011, U.S. Patent and Trademark Office, Alexandria, Virginia, dated May 4, 2012.
Dekeyser, M. and Davis, R.A., “Synthesis and Antifungal Activity of 5,6 Dihydro-3-methyl-1, 4-dioxin-2-carboxamides” J. Agric. Food. Chem. 46:287-2829 (1998).
Related Publications (1)
Number Date Country
20160150785 A1 Jun 2016 US
Divisions (1)
Number Date Country
Parent 10573066 US
Child 13800076 US
Continuations (1)
Number Date Country
Parent 13800076 Mar 2013 US
Child 15019466 US