Title of Invention

FUNGICIDAL MIXTURES

Abstract The invention discloses a fungicidal mixture comprising, as active components, (1) a sulfamoyl compound N,N-dimethyl-3-(3-bromo-6-fluoro-2- methylindole-1-sulfonyl)-[1,2,4]triazole-1-sulfonamide of the formula IA (2) at least one active compound selected from the following groups: A) strobilurins: azoxystrobin, dimoxystrobin, enestroburin, fluoxastrobin, kresoxim-methyl, metominostrobin, orysastrobin, picoxystrobin, pyraclostrobin ortrifloxystrobin; B) acylalanines: benalaxyl, metalaxyl, mefenoxam, ofurace, oxadixyl; C) cinnamides: dimethomorph, flumetover or flumorph; D) 5-chloro-7-(4-methylpiperidin-1-yl)-6-(2,4,6-trifluorophenyl)-[1,2,4]triazolo[1,5-a]pyrimidine of the formula II,
Full Text
The present invention relates to fungicidal mixtures comprising, as active components,
1) a sulfamoyl compound of the formula I

in which the substituents are as defined below:
R1 is hydrogen, halogen, cyano, C1C4-alkyl, C1-C2-haloalkyl, C1-C4-alkoxy, C1
C4-alkylthio, C1-C4-alkoxycarbonyl, phenyl, benzyl, formyl orCH=NOA;
A is hydrogen, C1-C4--alkyl, C1-C4-alkylcarbonyl; R2 is hydrogen, halogen, cyano, C1C4-alkyl,C1 -C1-haloalkyl, C1-C6-alkoxy-
carbonyl; R3 is halogen, cyano, nitro, C1-C4-alkyl, CrC2-haloalkyl, C1-C4-alkoxy,
CrC^alkylthio, d-C4-alkoxycarbonyl, formyl or CH=NOA; n is 0, 1, 2, 3 or 4; R4 is hydrogen, halogen, cyano, C1-C4Valkyl or C1-C2-haloalkyl;
and
2) at least one active compound selected from the following groups:
A) azoles, such as cyproconazole, difenoconazole, epoxiconazole, fiuquin-conazole, flusilazole, hexaconazole, imazalil, metconazole, myclobutanil, penconazole, prochloraz, prothioconazole, tebuconazole, triadimefon;tri-adimenol, triflumizole;
B) strobilurins, such as azoxystrobin, dimoxystrobin, fluoxastrobin, kresoxim-methyl, metominostrobin, orysastrobin, picoxystrobin, pyraclostrobin or tri-floxystrobin;
C) acylalanines, such as benalaxyl, metalaxyl, mefenoxam, ofurace, oxadixyl;
D) amine derivatives, such as spiroxamine;

E) anilinopyrimidines, such as pyrimethanil, mepanipyrim or cyprodinil;
F) dicarboximides, such as iprodione, procymidone, vinclozolin;
G) cinnamides and analogs, such as dimethomorph, flumetover or flumorph;
H) dithiocarbamates, such as ferbam, nabam, maneb, metam, metiram, propineb, polycarbamate, thiram, ziram, zineb;
I) heterocylic compounds, such as benomyl, boscalid, carbendazim, dithianon, famoxadone, fsnamidone, penthiopyrad, picobenzamid, proquinazid, quinoxyfen, thiophanate-methyl, triforine, or
5-chloro-7-(4-methylpipe-idin-1-yl)-6-(2,4,6-trifluorophenyl)-[1,2,4]triazolo[1,5-a]pyrimidine of the formula II,

K) sulfur and copper fungicides, such as Bordeaux mixture, copper acetate, copper oxychloride, basic copper sulfate;
L) nitrophenyl derivatives, such as dinocap;
M) phenylpyrroles, such as lenpiclonil or fludioxonil;
N) suifenic acid derivatives, such as captafol, dichlofluanid, tolylfluanid;
O) other fungicides, such as benthiavalicarb, chlorothalonil, cyflufenamid, di-clofluanid, diethofencarb, ethaboxam, fenhexamid, fluazinam, iprovalicarb, metrafenone, zoxamide;
oxime ether derivatives of the formula III,


in which
X is CrC4-haloalkoxy, n isO, 1,2 or 3,
R is halogen, C1-C4alkyl, C1-C4 haloalkyl, C1-C4-alkoxy or haloalkoxy; and
compounds of the formula IV,
IV
in which the variables are as defined below:
A is O or N;
B is N or a direct bond;
G is C or N;
R41 is C1-C4-alkyl;
R42 is C1-C4-alkoxy; and
R43 is halogen;
in a synergistically effective amount.
In a preferred embodiment, Sulfamoyl compound of Formula I, in the fungicidal mixture is :
N,N-dimethyl-3-(3-bromo-6-fluoro-2-methylindole-1-sulfonyl)-[1,2,4]triazole-1-sulfonamide of the formula IA


In another embodiment, the fungicidal mixture is a 3-component mixtures, which, apart from Sulfamoyl of Formula IA and atleast one active compound, selected from the groups A) to D), also comprises atleast one further active compound, selected from the groups E) to P):
E) azoles, such as cyproconazole, difenoconazole, enilconazole, epox-
iconazole, fluquinconazole, flusilazole, hexaconazole, imazalil, met-
conazole, myclobutanil, penconazole, prochloraz, prothioconazole,
tebuconazole, triadimefon, triadimenol, triflumizole;
F) amine derivatives, such as spiroxamine;
G) anilinopyrimidines, such as pyrimethanil, mepanipyrim or cyprodinil;
H) dicarboximides, such as iprodione, procymidone, vinclozolin;
I) dithiocarbamates, such as ferbam, nabam, maneb, metam, metiram, propineb, polycarbamate, thiram, ziram, zineb;
K) heterocylic compounds, such as benomyl, boscalid, carbendazim, dithianon, famoxadone, fenamidone, penthiopyrad, picobenzamid, proquinazid, quinoxyfen, thiophanate-methyl, triforine,
L) sulfur and copper fungicides, such as Bordeaux mixture, copper acet¬ate, copper oxychloride, basic copper sulfate;
M) nitrophenyl derivatives, such as dinocap;
N) phenylpyrroles, such as fenpiclonil or fludioxonil;
O) sulfenic acid derivatives, such as captafol, dichlofluanid, tolylfluanid;
P) other fungicides, such as benthiavalicarb, chlorothalonil, cyflufenam-id, diclofluanid, diethofencarb, ethaboxam, fenhexamid, fluazinam, iprovalicarb, mandipropamid, metrafenone, zoxamide;
oxime ether derivatives of the formula III,


in which
X is C1-C4rhaloalkoxy, n is 0,1, 2 or 3,
R is halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy or haloalkoxy; and
compounds of the formula IV,
IV
in which the variables are as defined below:
A is O or N;
B is N or a direct bond;
G is C or N;
R41 is Ci-Gralkyl;
R42 is C,-C4-alkoxy; and
R43 is halogen.
Moreover, the invention relates to a method for controlling harmful fungi using mixtures of a compound I with active compounds of groups A) to O) and to the use of the com¬pounds I with the active compounds of groups A) to O) for preparing such mixtures, and also to compositions comprising such mixtures.
The sulfamoyl compounds of the formula I referred to above as component 1, their pre¬paration and their action against harmful fungi are known from the literature (EP-A 10 31 571, JP-A 2001-192 381).
Mixtures of a sulfamoyl compound of the formula I with other active compounds are de¬scribed in WO 03/053145.

The active compounds of groups A) to O) mentioned above as component 2, their preparation and their action against narmful fungi are generally known (cf.: http://www.hclrss.demon.co.uk/index.html):
cyproconazole, 2-(4-chlorophenyl)-3-cyclopropyl-1-[1,2,4]triazol-1-ylbutan-2-ol
(US 4 664 696);
difenoconazole, 1-{2-[2-chloro-4-(4-chiorophenoxy)phenyl]-4-methyl-[1,3]dioxolan-2-
ylmethyl}-1H-[1,2,4]triazole (GB-A 2 098 607);
enilconazole (imazalil), 1 -[2-(2,4-dichlorophenyl)-2-(2-propenyloxy)ethyl]-1 H-imidazole
(Fruits, 1973, Vol.2B, p. 545);
epoxiconazole, (2RS,3SR)-1-[3-(2-chlorophenyl)-2,3-epoxy-2-(4-fluorophenyl)propyl]-
1H-1,2,4-triazole (EP-A 196 038);
fluquinconazol, 3-(2,4-dichlorophenyl)-6-fluoro-2-[1,2,4]triazol-1 -yl-3H-quinazolin-4-one
(Proc. Br. Crop Prot. Conf.-Pests Dis;., 5-3, 411 (1992));
fiusilazole, 1-{[bis-(4-fluorophenyl)methyisilanyl]methyl}-1H-[1,2,4]triazole (Proc. Br.
Crop Prot. Conf.-Pests Dis., 1, 413 (1984));
hexaconazole, (RS)-2-(2,4-dichlorophenyl)-1-(1H-1,2,4-triazol-1-yl)hexan-2-ol [CAS-RN
79983-71-4;
metconazole, 5-(4-chlorobenzyl)-2,2-dimethyl-1-[1,2,4]triazol-1-yImethylcyclopentanol
(GB 857 383);
myclobutanil, 2-(4-chlorophenyl)-2-[1,2,4]triazol-1-ylmethylpentanenitrile [CAS RN
88671-89-0;
penconazole, 1-[2-(2,4-dichlorophenyl)pentyl]-1H-[1,2,4]triazole (Pesticide Manual,
12th Ed. (2000), page 712);
prochloraz, N-propyl-N-[2-(2,4,6-trichlorophenoxy)ethyl]imidazole-1 -carboxamide (US
3 991 071);
prothioconazole, 2-[2-(1-chlorocyclopropyl)-3-(2-chlorophenyl)-2-hydroxypropyl]-2,4-
dihydro-[1,2,4]triazol-3-thione (WO 96/16048);
tebuconazole, 1-(4-chlorophenyl)-4/-dimethyl-3-[1,2,4]triazol-1-ylmethylpentan-3-ol
(EP-A 40 345);
triadimefon, 1 -(4-chlorophenoxy)-3,3-dimethyl-1 -(1 HA ,2,4-triazol-1 -yl)-2-butanone (BE
793897);
triadimenol,B-(4-chlorophenoxy)-a-(1,1-dimethylethyl)-1H-1,2,4-triazol-1-ethanol (DE
23 24 010);
triflumizole, (4-chloro-2-trifluoromethylphenyl)-(2-propoxy-1 -[1,2,4]triazol-1 -ylethyli-
dene)amine (JP-A 79/119 462);
azoxystrobin, methyl 2-{2-[6-(2-cyano-1-vinyipenta-1,3-dienyloxy)pyrimidin-4-
yloxy]phenyl}-3-methoxyacrylate (EP 382 375);

dimoxystrobin, (£)-2-(methoxyimino)-A/'-methyl-2-[a-(2,5-xylyloxy)-o-tolyl]acetamide (EP
477 631);
enestroburin, methyl 2-{2-[3-(4-chlorophenyl)-1-methylallylideneaminooxymethyl]-
phenyl}-3-methoxyacrylate (EP 936 213);
fluoxastrobin, (£)-{2-[6-(2-chlorophenoxy)-5-fluoropyrimidin-4-yloxy]phenyl}(5,6-
dihydro-1,4,2-dioxazin-3-yl)methanone O-methyloxime (WO 97/27189);
kresoxim-methyl, methyl (E>methoxyimino[ 253 213);
metominostrobin, (E)-2-(methoxyimino)-A/-methyl-2-(2-phenoxyphenyl)acetamide (EP
398 692);
orysastrobin, (2£)-2-(methoxyimino)-2-{2-[(3£,5E,6E)-5-(methoxyimino)-4,6-dimethyl-
2,8-dioxa-3,7-diazanona-3,6-dien-1-yl]phenyl}-A/-methylacetamide (WO 97/15552);
picoxystrobin, methyl 3-methoxy-2-[2-(6-trifluoromethylpyridin-2-yloxymethyl)phenyl]-
acrylate (EP 278 595);
pyraclostrobin, methyl /V-{2-[1-(4-chl(3rophenyl)-1H-pyrazol-3-yloxymethyl]phenyl}(A/-
methoxy)carbamate (WO 96/01256);
trifloxystrobin, methyl (E)-methoxyimino-{(/r)-a-[1 -(a,t7,o-trifluoro-m-tolyl)ethylidene-
aminooxy]-o-tolyl}acetate (EP 460 575);
benalaxyl, methyl A/-(phenylacetyl)-A'-(2,6-xylyl)-DL-alaninate (DE 29 03 612),
metalaxyl-M (mefenoxam), methyl W-(methoxyacetyl)-A/-(2,6-xylyl)-DL-alaninate (GB
15 00 581);
ofurace, (RS)-a-(2-chloro-W-2,6-xylylacetamido)-K-butyrolactone [CAS RN 58810-48-3];
oxadixyl; W-(2,6-dimethylphenyl)-2-methoxy-A/-(2-oxo-3-oxazolidinyl)acetamide
(GB 20 58 059);
spiroxamine, (8-tert-butyl-1,4-dioxaspiro[4.5]dec-2-yl)diethylamine (EP-A281 842);
pyrimethanil, (4,6-dimethylpyrimidin-2-yl)phenylamine (DD-A 151 404);
mepanipyrim, (4-methyl-6-prop-1-ynylpyrimidin-2-yl)phenylamine (EP-A224 339);
cyprodinil, (4-cyclopropyl-6-methylpyrimidin-2-yl)phenylamine (EP-A 310 550);
iprodione, N-isopropyl-3-(3,5-dichlorophenyl)-2,4-dioxoimidazolidine-1-carboxamide
(GB 13 12 536);
procymidone, A/-(3,5-dichlorophenyl)-1,2-dimethylcyclopropane-1,2-dicarboximide (US
3 903 090);
vinclozolin, 3-(3,5-dichlorophenyl)-5-Tiethyl-5-vinyloxazolidine-2,4-dione (DE-A
22 07 576);
dimethomorph, 3-(4-chlorophenyl)-3-(3,4-dimethoxyphenyl)-1-morpholin-4-ylpropenone
(EP 120 321);
flumetover, 2-(3,4-dimethoxypheny!)-A/-ethyl-(7,a,Qr-trifluoro-A/-methyl-p-toluamide
[AGROW No. 243, 22 (1995)];
flumorph, 3-(4-fluorophenyl)-3-(3,4-d!methoxyphenyl)-1-morpholin-4-ylpropenone (EP
860 438);

ferbam, iron(3+) dimethyldithiocarbanate (US 1 972 961);
nabam, disodium ethylenebis(dithiocarbamate) (US 2 317 765);
maneb, manganese ethylenebis(dithiocarbamate) (US 2 504 404);
metam, methyldithiocarbamic acid (US 2 791 605)
metiram, zinc ammoniate ethylenebi:s(dithiocarbamate) (US 3 248 400);
propineb, zinc propylenebis(dithiocarbamate) polymer (BE 611 960);
polycarbamate, bis(dimethylcarbamcdithioato-/fS,ArS')[//-[[1,2-ethanediylbis[carbamo-
dithioato-/cS,/rS']](2-)]]di[zinc] [CAS RN 64440-88-6];
thiram, bis(dimethylthiocarbamoyl) disulfide (DE 642 532);
ziram, dimethyldithiocarbamate [CAS RN 137-30-4];
zineb, zinc ethylenebis(dithiocarbamate) (US 2 457 674);
benomyl, N-butyl-2-acetylaminobenzoimidazole-1-carboxamide (US 3 631 176);
boscalid, 2-chloro-W-(4'-chlorobiphenyl-2-yl)nicotinamide (EP-A545 099);
carbendazim, methyl (1H-benzoimidazol-2-yI)carbamate (US 3 657 443);
dithianon, 5,10-dioxo-5,10-dihydronaiphtho[2,3-b][1,4]dithiine-2,3-dicarbonitrile (GB
857 383);
famoxadone, (RS)-3-anilino-5-methyl-5-(4-phenoxyphenyl)-1,3-oxazolidine-2,4-dione
[CASRN 131807-57-3];
fenamidone, (S)-1-anilino-4-methyl-2:-methylthio-4-phenylimidazolin-5-one [CAS RN
161326-34-7];
penthiopyrad, (RS)-A/-[2-(1,3-dimethylbutyl)-3-thienyl]-1-methyl-3-(trifluoromethyl)-1H-
pyrazole-4-carboxamide (JP 10130258);
fluopicolide (picobenzamid), 2,6-dichloro-N-(3-chloro-5-trifluoromethylpyridin-2-
ylmethyl)benzamide (WO 99/42447);
proquinazid, 6-iodo-2-propoxy-3-propylquinazolin-4(3/-/)-one (WO 97/48684);
quinoxyfen, 5,7-dichloro-4-(4-fluorophenoxy)quinoline (US 5 240 940);
thiophanate-methyl, 1,2-phenylenebis(iminocarbonothioyl)bis(dimethylcarbamate) (DE-
A 19 30 540);
triforine, W,A/'-{piperazine-1,4-diylbis[(trichloromethyl)methylene]}diformamide (DE
19 01 421);
5-chloro-7-(4-methylpiperidin-1-yl)-6-(2,4,6-trifluorophenyl)-[1,2,4]triazolo[1,5-a]pyrimi-
dine (WO 98/46607);
Bordeaux mixture, the mixture of CuS04 x 3Cu(OH)2 x 3CaS04 [CAS RN 8011-63-0]
copper acetate, Cu(OCOCH3)2 [CAS RN 8011-63-0];
copper oxychloride, Cu2CI(OH)3 [CAS RN 1332-40-7];
basic copper sulfate, CuS04 [CAS RN 1344-73-6];
dinocap, the mixture of 2,6-dinitro-4-octylphenyl crotonate and 2,4-dinitro-6-octylphenyl
crotonate, where "octyl" is a mixture of 1-methylheptyI, 1-ethylhexyl and 1-propylpentyl
(US 2 526 660);

fenpiclonil, 4-(2,3-dichlorophenyl)-1H-pyrrole-3-carbonitrile (Proc. 1988 Br. Crop Prot. Conf. - Pests Dis., Vol. 1, p. 65);
fludioxonil, 4-(2,2-difluorobenzo[1,3]dioxol-4-yl)-1H-pyrrole-3-carbonitrile (The Pesticide Manual, publ. The British Crop Protection Council, 10th Ed. (1995), p. 482); captafol, A/-(1,1,2,2-tetrachloroethylthio)cyclohex-4-ene-1,2-dicarboximide (Phytopa¬thology, Vol. 52, p. 754 (1962));
dichlofluanid, N-dichlorofluoromethylthio-W',/V'-dimethyl-W-phenylsulfamide (DE 11 93 498);
tolylfluanid, A/-dichlorofluoromethylthio-A/',A/'-dimethyl-W-p-tolylsulfamide (DE 11 93 498);
flubenthiavalicarb (benthiavalicarb), isopropyl {(S)-1-[(1R)-1-(6-fluorobenzothiazol-2-yl)ethylcarbamoyl]-2-methylpropyl}carbamate (JP-A 09/323 984); chlorothalonil, 2,4,5,6-tetrachloroisophthalonitrile (US 3 290 353); cyflufenamid, (Z)-A/-[a-(cyclopropylmethoxyimino)-2,3-difluoro-6-(trifluoromethyl)ben-zyl]-2-phenylacetamide (WO 96/19442); diclofluanid, 1.1-dichloro-A/-[(dimethylaminosulfonyl-1-fluoro-A/~ phenylmethanesulfenamide [CAS-RN 1085-98-9]; diethofencarb, isopropyl 3,4-diethoxycarbanilate (EP 78 663); ethaboxam, A/-(cyano-2-thienylmethyl)-4-ethyl-2-(ethylamino)-5-thiazolecarboxamide (EP-A 639 574);
fenhexamid, N-(2,3-dichloro-4-hydraxyphenyl)-1-methylcyclohexanecarboxamide (Proc. Br. Crop Prot. Conf. - Pests Dis., 1998, Vol. 2, p. 327);
fluazinam, 3-chloro-N-[3-chloro-2,6-(iinitro-4-(trifluoromethyl)phenyl]-5-(trifluoromethyl)-2-pyridinamine (The Pesticide Manual, publ. The British Crop Protection Council, 10th Ed. (1995), p. 474);
iprovalicarb, isopropyl [(1S)-2-methyl-1-(1-p-tolylethylcarbamoyl)propyl]carbamate (EP-A 472 996);
mandipropamid, (RS)-2-(4-chlorophenyl)-N-[3-methoxy-4-(prop-2-ynyloxy)phenethyl]-2-(prop-2-ynyloxy)acetamide (cf. WO 01/87822);
metrafenone, 3'-bromo-2,3,4,6'-tetramethoxy-2',6-dimethylbenzophenone (US 5 945 567);
zoxamide, (f?S)-3,5-dichloro-/V-(3-chloro-1 -ethyl-1 -methyl-2-oxopropyl)-p-toluamide [CASRN 156052-68-5];
oxime ether derivatives of the formula ill (WO 99/14188); compounds of the formula IV (WO 97/48648; WO 02/094797; WO 03/14103).
It is an object of the present invention, with a view to reducing the application rates and broadening the activity spectrum of the known compounds, to provide mixtures which, at a reduced total amount of active compounds applied, have improved activity against harmful fungi.

We have accordingly found that this object is achieved by the mixtures defined at the outset. Moreover, we have found that simultaneous, that is joint or separate, applica¬tion of the compound I and an active compound from groups A) to O) or successive application of the compound I and an active compound from groups A) to 0) allows better control of harmful fungi than is possible with the individual compounds (synergis¬tic mixtures).
The mixtures of a compound I and an active compound from groups A) to O) or the simultaneous, that is joint or separate, use of a compound I and an active compound from groups A) to O) are distinguished by being highly active against a wide range of phytopathogenic fungi, in particular from the classes of the Ascomycetes, Deuteromy-cetes, Oomycetes and Basidiomycetes. Some of them act systemically and can be used in crop protection as foliar fungicides, as fungicides for seed dressing and as soil-acting fungicides.
They are particularly important for controlling a multitude of fungi on various cultivated plants, such as bananas, cotton, vegetable species (for example cucumbers, beans and cucurbits), barley, grass, oats, coffee, potatoes, corn, fruit species, rice, rye, soya, tomatoes, grapevines, wheat, ornamental plants, sugar cane and also on a large num¬ber of seeds.
They are advantageously suitable for the control of the following phytopathogenic fungi: Blumeria graminis (powdery mildew) on cereals, Erysiphe cichoracearum and Sphaero-theca fuliginea on cucurbits, Podosphaera leucotricha on apples, Uncinula necatoron grapevines, Puccinia species on ceroais, Rhizoctonia species on cotton, rice and lawns, Ustilago species on cereals and sugar cane, Venturia inaequalis on apples, Bi-polaris and Drechslera species on cereals, rice and lawns, Septoria species on wheat, Botrytis cinema on strawberries, vegetables, ornamental plants and grapevines, My-cosphaerella species on bananas, peanuts and cereals, Pseudocercosporella her-potrichoides on wheat and barley, Pyricularia oryzae on rice, Phakopsora species on soybeans, Phytophthora infestans on potatoes and tomatoes, Pseudoperonospora species on cucurbits and hops, Plasmopara viticola on grapevines, Alternaria species on fruit and vegetables and also Fusarium and Verticillium species.
They are particularly suitable for controlling harmful fungi from the class of the Oomy¬cetes.
The compounds I and the active compounds from groups A) to O) can be applied si¬multaneously, that is jointly or separately, or in succession, the sequence, in the case

of separate application, generally not having any effect on the result of the control measures.
In the definitions of the symbols given in the formulae I to IV, collective terms were used which are generally representative for the following substituents:
halogen: fluorine, chlorine, bromine and iodine;
alkyl: saturated straight-chain or branched hydrocarbon radicals having 1 to 4 carbon atoms, for example Ci-C4-alkyl, such as methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl;
haloalkyl: straight-chain or branched alkyl groups having 1 or 2 carbon atoms (as men¬tioned above), where some or all of the hydrogen atoms in these groups may be re¬placed by halogen atoms as mentioned above: in particular Ci-C2-haloalkyl, such as chloromethyl, bromomethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoro-methyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1-chloroethyl, 1-bromoethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl, pentafluoroethyl or 1,1,1-trifluoroprop-2-yl.
The formula I represents in particular compounds in which the index n is 0, 1 or 2, pref¬erably 0 or 1.
In addition, preference is also given vo compounds I in which R1 is hydrogen, methyl, ethyl, n-, or isopropyl, fluorine, chlorine, bromine, iodine, methylthio, ethylthio, trifluoromethyl, pentafluoroethyl, cyano, phenyl orformyl, especially hydrogen, bromine or methyl, in particular methyl.
Preference is likewise given to compounds I in which R2 is hydrogen, fluorine, chlorine, bromine, iodine, methyl, trifluoromethyl, methoxycarbonyl, ethoxycarbonyl, n-propoxycarbonyl, isopropoxycarbonyl or n-butoxycarbonyl, especially chlorine, bro¬mine, methoxycarbonyl, n-propoxycarbonyl or n-butoxycarbonyl, in particular bromine.
The group R3 is preferably located in the 5- and/or 6-position(s). These compounds are particularly suitable for use in the mixtures according to the invention.
Preference is furthermore given to compounds I in which R3 is fluorine, chlorine, bro¬mine, iodine, cyano, nitro, methyl, ethyl, methoxy, trifluoromethyl, especially fluorine, chlorine, bromine, cyano, methyl, trifluoromethyl or methoxy, in particular fluorine.

In particular with a view to their use in the mixtures according to the invention, prefer¬ence is given to the compounds II compiled in the tables below.
Table 1
Compounds of the formula I in which n is zero and R4 is hydrogen and the combination
of R1 and R2 for a compound corresponds in each case to one row of table I
Table 2
Compounds of the formula I in which n is zero and R4 is fluorine and the combination of
R1 and R2 for a compound corresponds in each case to one row of table I
Table 3
Compounds of the formula I in which n is zero and R4 is chlorine and the combination
of R1 and R2 for a compound corresponds in each case to one row of table I
Table 4
Compounds of the formula I in which n is zero and R4 is methyl and the combination of
R1 and R2 for a compound corresponds in each case to one row of table I
Table 5
Compounds of the formula I in which n is 1, R3 is 4-fluoro and R4 is hydrogen and the
combination of R1 and R2 for a compound corresponds in each case to one row of table

Table 6
Compounds of the formula I in which n is 1, R3 is 5-fluoro and R4 is hydrogen and the
combination of R1 and R2 for a compound corresponds in each case to one row of table

Table 7
Compounds of the formula I in which n is 1, R3 is 6-fluoro and R4 is hydrogen and the
combination of R1 and R2 for a compound corresponds in each case to one row of table


Table 8 .
Compounds of the formula I in which n is 1, R3 is 7-fluoro and R4 is hydrogen, and the
combination of R1 and R2 for a compound corresponds in each case to one row of table

Table 9
Compounds of the formula I in which n is 1, R3 is 4-chloro and R4 is hydrogen, and the
combination of R1 and R2 for a compound corresponds in each case to one row of table

Table 10
Compounds of the formula I in which n is 1, R3 is 5-chloro and R4 is hydrogen, and the
combination of R1 and R2 for a compound corresponds in each case to one row of table

Table 11
Compounds of the formula I in which n is 1, R3 is 6-chloro and R4 is hydrogen, and the
combination of R1 and R2 for a compound corresponds in each case to one row of table

Table 12
Compounds of the formula I in which n is 1, R3 is 7-chloro and R4 is hydrogen, and the
combination of R1 and R2 for a compound corresponds in each case to one row of table

Table 13
Compounds of the formula I in which n is 1, R3 is 4-bromo and R4 is hydrogen, and the
combination of R1 and R2 for a compound corresponds in each case to one row of table

Table 14
Compounds of the formula I in which n is 1, R3 is 5-bromo and R4 is hydrogen, and the
combination of R1 and R2 for a compound corresponds in each case to one row of table

Table 15
Compounds of the formula I in which n is 1, R3 is 6-bromo and R4 is hydrogen, and the
combination of R1 and R2 for a compound corresponds in each case to one row of table


Table 16
Compounds of the formula I in which n is 1, R3 is 7-bromo and R4 is hydrogen, and the
combination of R1 and R2 for a compound corresponds in each case to one row of table

Table 17
Compounds of the formula I in which n is 1, R3 is 4-iodo and R4 is hydrogen, and the
combination of R1 and R2 for a compound corresponds in each case to one row of table

Table 18
Compounds of the formula I in which n is 1, R3 is 5-iodo and R4 is hydrogen, and the
combination of R1 and R2 for a compound corresponds in each case to one row of table

Table 19
Compounds of the formula I in which n is 1, R3 is 6-iodo and R4 is hydrogen, and the
combination of R1 and R2 for a compound corresponds in each case to one row of table

Table 20
Compounds of the formula I in which n is 1, R3 is 7-iodo and R4 is hydrogen, and the
combination of R1 and R2 for a compound corresponds in each case to one row of table

Table 21
Compounds of the formula I in which n is 1, R3 is 4-methyl and R4 is hydrogen, and the
combination of R1 and R2 for a compound corresponds in each case to one row of table

Table 22
Compounds of the formula I in which n is 1, R3 is 5-methyl and R4 is hydrogen, and the
combination of R1 and R2 for a compound corresponds in each case to one row of table

Table 23
Compounds of the formula I in which n is 1, R3 is 6-methyl and R4 is hydrogen, and the
combination of R1 and R2 for a compound corresponds in each case to one row of table


Table 24
Compounds of the formula I in which n is 1, R3 is 7-methyl and R4 is hydrogen, and the
combination of R1 and R2 for a compound corresponds in each case to one row of table

Table 25
Compounds of the formula I in which n is 1, R3 is 4-ethyl and R4 is hydrogen, and the
combination of R1 and R2 for a compound corresponds in each case to one row of table

Table 26
Compounds of the formula I in which n is 1, R3 is 5-ethyl and R4 is hydrogen, and the
combination of R1 and R2 for a compound corresponds in each case to one row of table

Table 27
Compounds of the formula I in which n is 1, R3 is 6-ethyl and R4 is hydrogen, and the
combination of R1 and R2 for a compound corresponds in each case to one row of table

Table 28
Compounds of the formula I in which n is 1, R3 is 7-ethyl and R4 is hydrogen, and the
combination of R1 and R2 for a compound corresponds in each case to one row of table

Table 29
Compounds of the formula I in which n is 1, R3 is 4-methoxy and R4 is hydrogen, and the combination of R1 and R2 for a compound corresponds in each case to one row of table
Table 30
Compounds of the formula I in which n is 1, R3 is 5-methoxy and R4 is hydrogen, and the combination of R1 and R2 for a compound corresponds in each case to one row of table
Table 31
Compounds of the formula I in which n is 1, R3 is 6-methoxy and R4 is hydrogen, and the combination of R1 and R2 for a compound corresponds in each case to one row of table


Table 32
Compounds of the formula I in which n is 1, R3 is 7-methoxy and R4 is hydrogen, and the combination of R1 and R2 for a compound corresponds in each case to one row of table
Table 33
Compounds of the formula I in which n is 1, R3 is 4-nitro and R4 is hydrogen, and the
combination of R1 and R2 for a compound corresponds in each case to one row of table

Table 34
Compounds of the formula I in which n is 1, R3 is 5-nitro and R4 is hydrogen, and the
combination of R1 and R2 for a compound corresponds in each case to one row of table

Table 35
Compounds of the formula I in which n is 1, R3 is 6-nitro and R4 is hydrogen, and the
combination of R1 and R2 for a compound corresponds in each case to one row of table

Table 36
Compounds of the formula I in which n is 1, R3 is 7-nitro and R4 is hydrogen, and the
combination of R1 and R2 for a compound corresponds in each case to one row of table

Table 37
Compounds of the formula I in which n is 1, R3 is 4-cyano and R4 is hydrogen, and the
combination of R1 and R2 for a compound corresponds in each case to one row of table

Table 38
Compounds of the formula I in which n is 1, R3 is 5-cyano and R4 is hydrogen, and the
combination of R1 and R2 for a compound corresponds in each case to one row of table

Table 39
Compounds of the formula I in which n is 1, R3 is 6-cyano and R4 is hydrogen, and the
combination of R1 and R2 for a compound corresponds in each case to one row of table


Table 40
Compounds of the formula I in which n is 1, R3 is 7-cyano and R4 is hydrogen, and the
combination of R1 and R2 for a compound corresponds in each case to one row of table

Table 41
Compounds of the formula I in which n is 1, R3 is 4-trifluoromethyI and R4 is hydrogen, and the combination of R1 and R2 for a compound corresponds in each case to one row of table
Table 42
Compounds of the formula I in which n is 1, R3 is 5-trifluoromethyl and R4 is hydrogen, and the combination of R1 and R2 for a compound corresponds in each case to one row of table
Table 43
Compounds of the formula I in which n is 1, R3 is 6-trifluoromethyl and R4 is hydrogen, and the combination of R1 and R2 for a compound corresponds in each case to one row of table
Table 44
Compounds of the formula I in which n is 1, R3 is 7-trifluoromethyl and R4 is hydrogen, and the combination of R1 and R2 for a compound corresponds in each case to one row of table
Table 45
Compounds of the formula I in which n is 1, R3 is 4-methoxycarbonyl and R4 is hydro¬gen, and the combination of R1 and R2 for a compound corresponds in each case to one row of table
Table 46
Compounds of the formula I in which n is 1, R3 is 5-methoxycarbonyl and R4 is hydro¬gen, and the combination of R1 and R2 for a compound corresponds in each case to one row of table
Table 47
Compounds of the formula I in which n is 1, R3 is 6-methoxycarbonyl and R4 is hydro¬gen, and the combination of R1 and R2 for a compound corresponds in each case to one row of table

Table 48
Compounds of the formula I in which n is 1, R3 is 7-methoxycarbonyl and R4 is hydro¬gen, and the combination of R1 and R2 for a compound corresponds in each case to one row of table I
Table 49
Compounds of the formula I in which n is 2, R3 is 5,6-difluoro and R4 is hydrogen, and the combination of R1 and R2 for a compound corresponds in each case to one row of table I
Table 50
Compounds of the formula I in which n is 2, R3 is 5,6-dichloro and R4 is hydrogen, and the combination of R1 and R2 for a compound corresponds in each case to one row of table I
Table 51
Compounds of the formula I in which n is 2, R3 is 5,6-dibromo and R4 is hydrogen, and the combination of R1 and R2 for a compound corresponds in each case to one row of table I
Table 52
Compounds of the formula I in which n is 2, R3 is 5,6-difluoro and R4 is fluorine, and the
combination of R1 and R2 for a compound corresponds in each case to one row of table
I
Table 53
Compounds of the formula I in which n is 2, R3 is 5,6-dichloro and R4 is fluorine, and the combination of R1 and R2 for a compound corresponds in each case to one row of table I
Table 54
Compounds of the formula I in which n is 2, R3 is 5,6-dibromo and R4 is fluorine, and the combination of R1 and R2 for a compound corresponds in each case to one row of table I
Table 55
Compounds of the formula I in which n is 2, R3 is 5,6-difluoro and R4 is chlorine, and the combination of R1 and R2 for a compound corresponds in each case to one row of table I

Table 56
Compounds of the formula I in which n is 2, R3 is 5,6-dichloro and R4 is chlorine, and the combination of R1 and R2 for a compound corresponds in each case to one row of table I
Table 57
Compounds of the formula I in which n is 2, R3 is 5,6-dibromo and R4 is chlorine, and the combination of R1 and R2 for a compound corresponds in each case to one row of table I
Table 58
Compounds of the formula I in which n is 2, R3 is 5,6-difluoro and R4 is methyl, and the
combination of R1 and R2 for a compound corresponds in each case to one row of table

Table 59
Compounds of the formula I in which n is 2, R3 is 5,6-dichloro and R4 is methyl, and the
combination of R1 and R2 for a compound corresponds in each case to one row of table

Table 60
Compounds of the formula I in which n is 2, R3 is 5,6-dibromo and R4 is methyl, and the
combination of R1 and R2 for a compound corresponds in each case to one row of table












Particular preference is given to the combinations of one of the compounds 1-135, 1-161 and 1-187 of table 3, I-27 of table 4, I-62 of table 7 and I-22 of table 55 with one of the active compounds, defined at the outset, from groups A) to O), especially preferred is

the compound 1-62 of table 7, N,N-dimethyl-3-(3-bromo-6-fluoro-2-methylindole-1-sulfonyl)-[1,2,4]triazole-1 -sulfonamide (compound IA).
A preferred embodiment of the invention provides mixtures of a compound I with the compound of the formula II.
A further embodiment of the invention provides mixtures of a compound I with an oxime ether derivative of the formula III.
From among the compounds of the formula III, preference is given to those in which X is a difluoromethoxy group. In addition, particular preference is given to compounds of the formula III in which the index n is zero.
Particularly preferred compounds III are especially the compounds listed in table III below:


Another embodiment of the invention provides mixtures of a compound I with a compound of the formula IV.
Preference is given to compounds of the formula IV in which R41 is n-propyl or n-butyl, in particular n-propyl.
In addition, particular preference is given to compounds of the formula IV in which R43 is iodine or bromine, in particular iodine.
The formula IV represents in particular compounds of the formulae IV. 1, IV.2 and IV.3:

in which the variables have the meanings given for formula IV.
The compound of the formula IV. 1 in which R41 is n-propyl, R42 is n-propoxy and R43 is iodine is known under the common name proquinazid (compound IV. 1-1). Mixtures of a compound of the formula I and proquinazid are a preferred embodiment of the invention.
In addition, mixtures comprising a compound of the formula I and a compound of the formula IV.2 are also a preferred embodiment of the invention.
Especially preferred are the mixtures with a compound I and one of the following compounds of the formula IV.2:
NO R41 R42 R43
IV.2-1 CH2CH2CH3 OCH3 i
IV.2-2 CH2CH2CH2CH3 OCH2CH3 I
IV.2-3 CH2CH2CH3 OCH2CH3 i
IV.2-4 CH2CH2CH3 I OCH(CH3)2 i
A further preferred embodiment of the invention relates to mixtures of a compound I and one of the following compounds of the formula IV.3:
No I R41 R42 R43
IV.3-1 CH2CH2CH3 OCH3 j
IV.3-2 CH2CH2CH2CH3 OCH2CH3 I


Here, particular preference is given to mixtures of a compound I with compounds IV.3-6 or IV.3-12, especially IV.3-6.
A further preferred embodiment of the mixtures according to the invention relates to the combination of one of the abovementioned compounds of the formula I and strobilurins, such as azoxystrobin, fluoxastrobin, picoxystrobin, pyraclostrobin or trifloxystrobin.
A further preferred embodiment of the mixtures according to the invention relates to the combination of one of the abovementioned compounds of the formula I and acyla-lanines, such as benalaxyl, metalaxyl, mefenoxam, ofurace oroxadixyl.
A further preferred embodiment of the mixtures according to the invention relates to the combination of one of the abovementioned compounds of the formula I and cinnamides and analogs, such as dimethomorph, flumetoverorflumorph.
A further preferred embodiment of the mixtures according to the invention relates to the combination of one of the abovementioned compounds of the formula I and heterocyc¬lic compounds, such as dithianon, picobenzamid, thiophanate-methyl ortriforine.
A further preferred embodiment of the mixtures according to the invention relates to the combination of one of the abovementioned compounds of the formula I and sulfur or copper fungicides, such as Bordeaux mixture, copper acetate, copper oxychloride, basic copper sulfate.
A further preferred embodiment of the mixtures according to the invention relates to the combination of one of the abovementioned compounds of the formula I and an active compound from the group consisting of captafol, dichlofluanid, tolylfluanid, benthiavali-

carb, chlorothalonil, cyflufenamid, diclofluanid, diethofencarb, ethaboxam, fenhexamid, fluazinam, iprovalicarb, metrafenone and zoxamide.
When preparing the mixtures, it is praferred to employ the pure active compounds I and II, to which further active compounds; against harmful fungi or against other pests, such as insects, arachnids or nematodes, or else herbicidal or growth-regulating active compounds or fertilizers can be added as further active components according to need.
Usually, mixtures of the compound I with an active compound from groups A) to O) are employed. However, in certain cases; mixtures of the compound I with two or, if appro¬priate, more active components may be advantageous.
Suitable further active components in the above sense are in particluar the active com¬pounds, mentioned at the outset, from groups A) to 0) and in particular the preferred active compounds mentioned above.
The compound I and the active compound from groups A) to O) are usually applied in a weight ratio of from 100:1 to 1:100, preferably from 20:1 to 1:20, in particular from 10:1 to 1:10.
The further active components are, if desired, added in a ratio of from 20:1 to 1:20 to the compound I.
Depending on the type of compound and the desired effect, the application rates of the mixtures according to the invention are from 5 g/ha to 2000 g/ha, preferably from 50 to 900 g/ha, in particular from 50 to 750 g/ha.
Correspondingly, the application rates for the compound I are generally from 1 to 1000 g/ha, preferably from 10 to 900 g/ha, in particular from 20 to 750 g/ha.
Correspondingly, the application rates for the active compound from groups A) to O) are generally from 1 to 2000 g/ha, preferably from 10 to 900 g/ha, in particular from 40 to 500 g/ha.
In the treatment of seed, application rates of mixture are generally from 1 to 1000 g/100 kg of seed, preferably from 1 to 750 g/100 kg, in particular from 5 to 500g/100kg.
The method for controlling harmful fungi is carried out by the separate or joint applica¬tion of the compound I and the active compound from groups A) to O) or the mixtures

of the compound I and the active compound from groups A) to 0) by spraying or dust¬ing the seeds, the plants or the soil before or after sowing of the plants or before or after emergence of the plants.
The mixtures according to the invention, or the compound I and the active compound from groups A) to O), can be converted into the customary formulations, for example solutions, emulsions, suspensions, custs, powders, pastes and granules. The use form depends on the particular intended purpose; in each case, it should ensure a fine and even distribution of the compound according to the invention.
The formulations are prepared in a known manner, for example by extending the active compound with solvents and/or carriers, if desired using emulsifiers and dispersants. Solvents/auxiliaries suitable for this purpose are essentially:
- water, aromatic solvents (for example Solvesso products, xylene), paraffins (for example mineral oil fractions), alcohols (for example methanol, butanol, pentanol, benzyl alcohol), ketones (for example cyclohexanone, gamma-butyrolactone), pyrrolidones (NMP, NOP), acetates (glycol diacetate), glycols, fatty acid dimethylamides, fatty acids and fatty acid esters. In principle, solvent mixtures may also be used,
- carriers such as ground natural minerals (for example kaolins, clays, talc, chalk) and ground synthetic minerals (for example highly disperse silica, silicates); emulsifiers such as nonionogenic and anionic emulsifiers (for example polyoxyethylene fatty alcohol ethers, alkylsulfonates and arylsulfonates) and dispersants such as lignosulfite waste liquors and methylcellulose.
Suitable for use as surfactants are alkali metal, alkaline earth metal and ammonium salts of lignosulfonic acid, naphthalenesulfonic acid, phenolsulfonic acid, dibutylnaphthalenesulfonic acid, alkylarylsulfonates, alkyl sulfates, alkylsulfonates, fatty alcohol sulfates, fatty acids and sulfated fatty alcohol glycol ethers, furthermore condensates of sulfonated naphthalene and naphthalene derivatives with formaldehyde, condensates of naphthalene or of naphthalenesulfonic acid with phenol and formaldehyde, polyoxyethylene octylphenyl ether, ethoxylated isooctylphenol, octylphenol, nonylphenol, alkylphenyl polyglycol ethers, tributylphenyl polyglycol ether, tristearylphenyl polyglycol ether, alkylaryl polyether alcohols, alcohol and fatty alcohol ethylene oxide condensates, ethoxylated castor oil, polyoxyethylene alkyl ethers, ethoxylated polyoxypropylene, lauryl alcohol polyglycol ether acetal, sorbitol esters, lignosulfite waste liquors and methylcellulose.
Substances which are suitable for the preparation of directly sprayable solutions, emulsions, pastes or oil dispersions are mineral oil fractions of medium to high boiling

point, such as kerosene or diesel oil furthermore coal tar oils and oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, for example toluene, xylene, paraffin, tetrahydronaphthalene, alkylated naphthalenes or their derivatives, methanol, ethanol, propanol, butanol, cyclohexanol, cyclohexanone, isophorone, highly polar solvents, for example dimethyl sulfoxide, N-methylpyrrolidone and water.
Powders, materials for spreading and dustable products can be prepared by mixing or concomitantly grinding the active substances with a solid carrier.
Granules, for example coated granues, impregnated granules and homogeneous granules, can be prepared by binding the active compounds to solid carriers. Examples of solid carriers are mineral earths such as silica gels, silicates, talc, kaolin, attaclay, limestone, lime, chalk, bole, loess, clay, dolomite, diatomaceous earth, calcium sulfate, magnesium sulfate, magnesium oxide, ground synthetic materials, fertilizers, such as, for example, ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas, and products of vegetable origin, such a:; cereal meal, tree bark meal, wood meal and nutshell meal, cellulose powders and other solid carriers.
In general, the formulations comprise from 0.01 to 95% by weight, preferably from 0.1 to 90% by weight, of the active compounds. The active compounds are employed in a purity of from 90% to 100%, preferably 95% to 100% (according to NMR spectrum).
The following are examples of formulations: 1. Products for dilution with water
A) Water-soluble concentrates (SL)
10 parts by weight of the active compounds are dissolved in water or in a water-soluble solvent. As an alternative, wetters or other auxiliaries are added. The active compound dissolves upon dilution with water.
B) Dispersible concentrates (DC)
20 parts by weight of the active compounds are dissolved in cyclohexanone with addition of a dispersant, for example polyvinylpyrrolidone. Dilution with water gives a dispersion.
C) Emulsifiable concentrates (EC)
15 parts by weight of the active compounds are dissolved in xylene with addition of calcium dodecylbenzenesulfonate and castor oil ethoxylate (in each case 5% strength). Dilution with water gives an emulsion.
D) Emulsions (EW, EO)

40 parts by weight of the active compounds are dissolved in xylene with addition of calcium dodecylbenzenesulfonate and castor oil ethoxylate (in each case 5% strength). This mixture is introduced into water by means of an emulsifying machine (Ultraturrax) and made into a homogeneous emulsion. Dilution with water gives an emulsion.
E) Suspensions (SC, OD)
In an agitated ball mill, 20 parts by weight of the active compounds are comminuted with addition of dispersants, wetters and water or an organic solvent to give a fine active compound suspension. Dilution with water gives a stable suspension of the active compound.
F) Water-dispersible granules and water-soluble granules (WG, SG)
50 parts by weight of the active compounds are ground finely with addition of dispersants and wetters and prepared as water-dispersible or water-soluble granules by means of technical appliances (for example extrusion, spray tower, fluidized bed). Dilution with water gives a stable dispersion or solution of the active compound.
G) Water-dispersible powders anc. water-soluble powders (WP, SP)
75 parts by weight of the active compounds are ground in a rotor-stator mill with addition of dispersants, wetters and silica gel. Dilution with water gives a stable dispersion or solution of the active compound.
2. Products to be applied undiluted
H) Dustable powders (DP)
5 parts by weight of the active compounds are ground finely and mixed intimately with
95% of finely divided kaolin. This gives a dustable product.
I) Granules (GR, FG, GG, MG)
0.5 part by weight of the active compounds is ground finely and associated with 95.5% carriers. Current methods are extrusion, spray-drying or the fluidized bed. This gives granules to be applied undiluted.
J) ULV solutions (UL)
10 parts by weight of the active compounds are dissolved in an organic solvent, for
example xylene. This gives a product to be applied undiluted.
The active compounds can be used as such, in the form of their formulations or the use forms prepared therefrom, for example in the form of directly sprayable solutions, powders, suspensions or dispersions, emulsions, oil dispersions, pastes, dustable

products, materials for spreading, or granules, by means of spraying, atomizing, dusting, spreading or pouring. The use forms depend entirely on the intended purposes; they are intended to ensure in each case the finest possible distribution of the active compounds according to tie invention.
Aqueous use forms can be prepared from emulsion concentrates, pastes or wettable powders (sprayable powders, oil dispersions) by adding water. To prepare emulsions, pastes or oil dispersions, the substances, as such or dissolved in an oil or solvent, can be homogenized in water by means of a wetter, tackifier, dispersant or emulsifier. However, it is also possible to prepa'e concentrates composed of active substance, wetter, tackifier, dispersant or emulsifier and, if appropriate, solvent or oil, and such concentrates are suitable for dilution with water.
The active compound concentrations in the ready-to-use preparations can be varied within relatively wide ranges. In general, they are from 0.0001 to 10%, preferably from 0.01 to1%.
The active compounds may also be jsed successfully in the ultra-low-volume process (ULV), it being possible to apply formulations comprising over 95% by weight of active compound, or even to apply the active compound without additives.
Oils of various types, wetters, adjuvants, herbicides, fungicides, other pesticides, or bactericides may be added to the active compounds, even, if appropriate, not until immediately prior to use (tank mix), These agents are typically admixed with the compositions according to the invention in a weight ratio of from 1:10 to 10:1.
The compounds I and A) to O) or the mixtures or the corresponding formulations are applied by treating the harmful fungi, the plants, seeds, soils, areas, materials or spaces to be kept free from them with a fungicidally effective amount of the mixture or, in the case of separate application, of the compounds I and A) to O). Application can be carried out before or after infection by the harmful fungi.
The fungicidal effect of the compound and the mixtures can be demonstrated by the following tests:
The active compounds, separately or jointly, were prepared as a stock solution comprising 0.25% by weight of active compound in acetone or DMSO. 1% by weight of the emulsifier Uniperol® EL (wetting agent having emulsifying and dispersant action based on ethoxylated alkylphenols) was added to this solution, and the mixture was diluted with water to the desired concentration.

The visually determined percentages, of infected leaf areas were converted into efficacies in % of the untreated control:
The efficacy (E) is calculated as follows using Abbot's formula:
E = (1 -a/0)- 100
a corresponds to the fungicidal infection of the treated plants in % and
corresponds to the fungicidal infection of the untreated (control) plants in %
An efficacy of 0 means that the infection level of the treated plants corresponds to that of the untreated control plants; an efficacy of 100 means that the treated plants were not infected.
The expected efficacies of mixtures of active compounds were determined using Colby's formula (Colby, S.R. "Calculating synergistic and antagonistic responses of herbicide Combinations", Weeds, 15, 20-22, 1967) and compared with the observed efficacies.
Colby's formula:
E = x + y-x-y/100
E expected efficacy, expressed in % of the untreated control, when using the mixture of the active compounds A and B at the concentrations a and b
x efficacy, expressed in % of the untreated control, when using the active compound A at the concentration a
y efficacy, expressed in % of the untreated control, when using the active compound B at the concentration b
Use example 1 - activity against late blight on tomatoes caused by Phytophthora infestans, protective application
Leaves of potted tomato plants were sprayed to runoff point with an aqueous suspension having the concentration of active compound given below. The next day, the leaves were infected with an aqueous sporangia suspension of Phytophthora infestans. The plants were then placed in a water-vapor-saturated chamber at temperatures

between 18 and 20°C. After 6 days, the blight on the untreated but infected control plants had developed to such an extent that the infection could be determined visually in %.
Table A - individual active compounds
Concentration of active
Active compound / Efficacy in % of the
Example compound in the spray
mixing ratio untreated control
liquor [ppm]
1 control (untreated) - (90 % infection)
2 ' I-62, Tab.7 (IA) 1 56
4 6
3 II 1 0
0.25 0
Table B - mixtures according to the invention
I Active compound mixture
Observed Calculated
Example Concentration
efficacy efficacy )
Mixing ratio
IA + II
4 1+4 ppm 89 56
1:4 _____
5 1 + 1 ppm 78 56
1:1 1A+11
6 1 + 0.25 ppm 67 56
4:1 *) efficacy calculated using Colby's formula
The test results show that, by virtue of strong synergism, the activity of the mixtures according to the invention is considerably higher than had been predicted using Colby's formula.

A fungicidal mixture comprising, as active components,
(1) a sulfamoyl compound N,N-dimethyl-3-(3-bromo-6-fluoro-2-
methylindole-1-sulfonyl)-[1,2,4]triazole-1-sulfonamide of the formula IA

(2) at least one active compound selected from the following groups:
A) strobilurins: azoxystrobin, dimoxystrobin, enestroburin, fluoxastrobin,
kresoxim-methyl, metominostrobin, orysastrobin, picoxystrobin,
pyraclostrobin or trifloxystrobin;
B) acylalanines: benalaxyl, metalaxyl, mefenoxam, ofurace, oxadixyl;
C) cinnamides: dimethomorph, flumetover or flumorph;
D) 5-chloro-7-(4-methylpiperidin-1-yl)-6-(2,4,6-trifluorophenyl)-
[1,2,4]triazolo[1,5-a]pyrimidine of the formula II,

The fungicidal mixture as claimed in claim 1, wherein the component 2) is azoxystrobin, fluoxastrobin, picoxystrobin, pyraclostrobin or trifloxystrobin.
The fungicidal mixture as claimed in claim 1, wherein the component 2) is benalaxyl, metalaxyl, mefenoxam, ofurace or oxadixyl.

The fungicidal mixture as claimed in claim 1, wherein the component 2) is dimethomorph, flumetover or flumorph.
The fungicidal mixture as claimed in claim 1, wherein the component 2) is the compound of the formula II.
The fungicidal mixture as claimed in any one of the claims 1 to 5, wherein the mixtures optionally comprises atleast one further active compound as a third component, selected the groups E) to P):
E) azoles, such as cyproconazole, difenoconazole, enilconazole, epox-
iconazole, fluquinconazole, flusilazole, hexaconazole, imazalil, met-
conazole, myclobutanil, penconazole, prochloraz, prothioconazole,
tebuconazole, triadimefon, triadimenol, triflumizole;
F) amine derivatives, such as spiroxamine;
G) anilinopyrimidines, such as pyrimethanil, mepanipyrim or cyprodinil;
H) dicarboximides, such as iprodione, procymidone, vinclozolin;
I) dithiocarbamates, such as ferbam, nabam, maneb, metam, metiram, propineb, polycarbamate, thiram, ziram, zineb;
K) heterocylic compounds, such as benomyl, boscalid, carbendazim, dithianon, famoxadone, fenamidone, penthiopyrad, picobenzamid, proquinazid, quinoxyfen, thiophanate-methyl, triforine,
L) sulfur and copper fungicides, such as Bordeaux mixture, copper acet¬ate, copper oxychloride, basic copper sulfate;
M) nitrophenyl derivatives, such as dinocap;
N) phenylpyrroles, such as fenpiclonil or fludioxonil;
O) sulfenic acid derivatives, such as captafol, dichlofluanid, tolylfluanid;
P) other fungicides, such as benthiavalicarb, chlorothalonil, cyflufenam-id, diclofluanid, diethofencarb, ethaboxam, fenhexamid, fluazinam, iprovalicarb, mandipropamid, metrafenone, zoxamide;
oxime ether derivatives of the formula III,


in which
X is C1-C4-haloalkoxy, n isO, 1,2 or 3,
R is halogen, CrC4-alkyl,-C1-C4-haloalkyl, C1-C4-alkoxy or haloalkoxy; and
compounds of the formula IV, O
R43 11 R41
'•\ 42 IV
in which the variables are as defined below:
A is O or N;
B is N or a direct bond;
G is C or N;
R41 is C1-C4-alkyl;
R42 is C1-C4-alkoxy; and
R43 is halogen.
The fungicidal mixture as claimed in any one of the claims 1 to 6, compris¬ing a compound of the formula I and an active compound from groups A) to D) in a weight ratio of from 20:1 to 1:20.
A composition, comprising a solid or liquid carrier and a mixture according to any one of the claims 1 to 7.


The invention discloses a fungicidal mixture comprising, as active components,
(1) a sulfamoyl compound N,N-dimethyl-3-(3-bromo-6-fluoro-2-
methylindole-1-sulfonyl)-[1,2,4]triazole-1-sulfonamide of the formula IA

(2) at least one active compound selected from the following groups:
A) strobilurins: azoxystrobin, dimoxystrobin, enestroburin, fluoxastrobin, kresoxim-methyl, metominostrobin, orysastrobin, picoxystrobin, pyraclostrobin ortrifloxystrobin;
B) acylalanines: benalaxyl, metalaxyl, mefenoxam, ofurace, oxadixyl;
C) cinnamides: dimethomorph, flumetover or flumorph;
D) 5-chloro-7-(4-methylpiperidin-1-yl)-6-(2,4,6-trifluorophenyl)-[1,2,4]triazolo[1,5-a]pyrimidine of the formula II,

Documents:

02521-kolnp-2006 abstract.pdf

02521-kolnp-2006 claims.pdf

02521-kolnp-2006 correspondence others.pdf

02521-kolnp-2006 description (complete).pdf

02521-kolnp-2006 form-1.pdf

02521-kolnp-2006 form-3.pdf

02521-kolnp-2006 form-5.pdf

02521-kolnp-2006 international search report.pdf

02521-kolnp-2006 others.pdf

02521-kolnp-2006 pct form.pdf

02521-kolnp-2006 priority document.pdf

02521-kolnp-2006-correspondence others-1.1.pdf

02521-kolnp-2006-form-3-1.1.pdf

02521-kolnp-2006-form-5-1.1.pdf

2521-KOLNP-2006-CORRESPONDENCE 1.1.pdf

2521-kolnp-2006-correspondence 1.2.pdf

2521-KOLNP-2006-CORRESPONDENCE.pdf

2521-kolnp-2006-examination report 1.2.pdf

2521-kolnp-2006-form 18 1.2.pdf

2521-KOLNP-2006-FORM 3 1.1.pdf

2521-kolnp-2006-form 3 1.2.pdf

2521-kolnp-2006-form 5 1.2.pdf

2521-kolnp-2006-gpa 1.2.pdf

2521-kolnp-2006-granted-abstract.pdf

2521-kolnp-2006-granted-claims.pdf

2521-kolnp-2006-granted-description (complete).pdf

2521-kolnp-2006-granted-form 1.pdf

2521-kolnp-2006-granted-form 2.pdf

2521-kolnp-2006-granted-specification.pdf

2521-kolnp-2006-others 1.2.pdf

2521-KOLNP-2006-PETITIONS UNDER RULE 137.pdf

2521-kolnp-2006-reply to examination report 1.2.pdf

2521-kolnp-2006-translated copy of priority document 1.2.pdf

abstract-02521-kolnp-2006.jpg


Patent Number 246203
Indian Patent Application Number 2521/KOLNP/2006
PG Journal Number 08/2011
Publication Date 25-Feb-2011
Grant Date 21-Feb-2011
Date of Filing 04-Sep-2006
Name of Patentee BASF AKTIENGESELLSCHAFT
Applicant Address 67056 LUDWIGSHAFEN
Inventors:
# Inventor's Name Inventor's Address
1 GROTE, THOMAS IM HOHNHAUSEN 18, 67157 WACHENHEIN GERMANY
2 TORMO I BLASCO, JORDI CARL-BENZ-STR. 10-3, 69514 LAUDENBACK GERMANY
3 SCHERER, MARIA HERMANN-JURGENS-STR.30, 76829 GODRAMSTEIN, GERMANY
4 STIERL, REINHARD JAHNSTR.8, 67251 FREINSHEIM, GERMANY
5 STRATHMANN, SIEGFRIED DONNERSBERGSTR.9, 67117 LIMBURGERHOF, GERMANY
6 SCHOFL, ULRICH ERLENSTR.8, 68782 BRUHL, GERMANY
7 SUAREZ-CERVIERI MIGUEL OCTAVIO EICHSTR.52, 67434 NEUSTADT-HAMBACH GERMANY
8 NIEDENBRUCK MATTHIAS ALBERT-EINSTEIN-ALLEE 3, 67117 LIMBURGERHOF, GERMANY
9 GEWEHR MARKUS GOETHESTR.21, 56288 KASTELLAUN, GERMANY
10 MULLER BERND STOCKINGER STR.7, 67227 FRANKENTHAL, GERMANY
PCT International Classification Number A01N 43/653
PCT International Application Number PCT/EP2005/004387
PCT International Filing date 2005-04-23
PCT Conventions:
# PCT Application Number Date of Convention Priority Country
1 102004025032.4 2004-05-18 Germany
2 102004021766.1 2004-04-30 Germany