Fungicidal combinations of active substances

IS 2 197 124 T3

DESCRIPTION

Combinations of fungicidal active products.

The present invention relates to new combinations of active ingredients, which are constituted by a known derivative of fluorine-benzothiazole, on the one hand, and by other known active ingredients, on the other hand, and which are very well suited for the fight against phytopathogenic fungi.

Isopropyl 1 - ({[1- (6-fluoro-1,3-benzothiazol-2-yl) ethyl] -amino} carbonyl) -2-methylpropylcarbamate is already known to have fungicidal properties (see EP A1-775 696 ). The activity of this product is good but nevertheless leaves something to be desired in some cases with low application rates.

Furthermore, it is already known that a large number of triazole derivatives, aniline derivatives, dicarboxamides and other heterocycles can be used to control fungi (see publications EP-A 0 040 345, DE-A 22 01 063, DE-A 23 24 010, Pesticide Manual, 9 th. Edition (1991), pages 249 and 827, EP-A 0 382 375 and EP-A 0 515 901). The effect of these products is not always sufficient either at low application rates.

Finally, it is also known that 1 - [(6-chloro-3-pyridinyl) -methyl] -2-nitro-2-imidazolidinimine can be used to control animal pests, such as insects (see Pesticide Manual, 9 th. Edition (1991), page 491). However, the fungicidal properties of this product have not yet been described.

Furthermore, 1- (3,5-dimethyl-isoxazole-4-sulfonyl) -2-chloro-6,6-difluoro- [1,3] -dioxolo- [4,5f] -benzimidazole is known to have fungicidal properties ( see WO 97-06171).

It is further known that substituted azadioxacycloalkanes show a fungicidal effect (see EP-B-712 396).

Finally, it is also known that substituted halogenopyrimidines have fungicidal properties (see DE-A1-196 46 407, EP-B-712 396).

It has now been found that new active compound combinations consisting of a fluorobenzothiazole derivative of the formula

<img file="ES2197124T3_D0001.tif" />

^Y (1) a triazole derivative of the formula

<img file="ES2197124T3_D0002.tif" />

in which

X means chlorine or phenyl, and Y means

<img file="ES2197124T3_D0003.tif" />

me

ES 2 197 124 T3 (2) the triazole derivative of the formula

<img file="ES2197124T3_D0004.tif" />

and / or (3) an aniline derivative of the formula

<img file="ES2197124T3_D0005.tif" />

in which

R¹ means hydrogen or methyl, and / or (4) the N- [1- (4-chloro-phenyl) -ethyl] -2,2-dichloro-1-ethyl-3-methyl-cyclopropane-carboxamide of the formula

<img file="ES2197124T3_D0006.tif" />

and / or (5) zinc propylene-1,2-bis- (dithiocarbamidate) of the formula

<img file="ES2197124T3_D0007.tif" />

and / or (6) at least one thiocarbamate of the formula

<img file="ES2197124T3_D0008.tif" />

IS 2 197 124 T3

Me = Zn or Mn or mixtures of Zn and Mn and / or (7) the aniline derivative of the formula

<img file="ES2197124T3_D0009.tif" />

and / or (8) the compound of the formula

<img file="ES2197124T3_D0010.tif" />

and / or (9) the benzothiadiazole derivative of the formula and / or

<img file="ES2197124T3_D0011.tif" />

<img file="ES2197124T3_D0012.tif" />

(10) 8-t-butyl-2- (N-ethyl-Nn-propyl-amino) -methyl-1,4-dioxaspiro [5,4] -decane of the formula and / or (11) the compound of the formula

IS 2 197 124 T3

<img file="ES2197124T3_D0013.tif" />

and / or (12) the compound of the formula

<img file="ES2197124T3_D0014.tif" />

(Trifloxystrobin) and / or (13) the compound of the formula

<img file="ES2197124T3_D0015.tif" />

and / or (14) the cyanoxime derivative of the formula

<img file="ES2197124T3_D0016.tif" />

and / or (15) a pyrimidine derivative of the formula

<img file="ES2197124T3_D0017.tif" />

ES 2 197 124 T3 in which

R² means methyl, - ('ξ (' - (Ί I₃ (Mepanipyrim) or cyclopropyl (Cyprodinyl), and / or (16) an aniline derivative of the formula

<img file="ES2197124T3_D0018.tif" />

and / or (17) the morpholine derivative of the formula

<img file="ES2197124T3_D0019.tif" />

and / or (18) the phthalimide derivative of the formula

<img file="ES2197124T3_D0020.tif" />

and / or (19) the phosphorus compound of the formula

<img file="ES2197124T3_D0021.tif" />

and / or (20) the hydroxyethyl-triazole derivative of the formula

ES 2 197 124 T3 and / or

<img file="ES2197124T3_D0022.tif" />

<img file="ES2197124T3_D0023.tif" />

(21) the 1 - [(6-chloro-3-pyridinyl) -methyl] -N-nitro-2-imidazolidinimine of the formula and / or (22) the oxazolidinedione of the formula

<img file="ES2197124T3_D0024.tif" />

and / or (23) the benzamide derivative of the formula

<img file="ES2197124T3_D0025.tif" />

and / or (24) a guanidine derivative of the formula

IS 2 197 124 T3

R³ R³

R — M— (CHJ.-IN— (CHJJ-NH (XXV)

Π x (2 + m) CH₃COOH where m means an integer from 0 to 5 and

R³ means hydrogen (17 to 23%) or the rest of the formula

C = NH

I nh₂ (77 to 83%).

and / or (25) the triazole derivative of the formula

<img file="ES2197124T3_D0026.tif" />

and / or (26) the halogen-benzimidazole of the formula

<img file="ES2197124T3_D0027.tif" />

(XXVII) and / or (27) the halogenopyrimidine of the formula

<img file="ES2197124T3_D0028.tif" />

ES 2 197 124 T3 and / or (28) tetrachloro-isophthalo-dinitrile of the formula

<img file="ES2197124T3_D0029.tif" />

and / or (29) the compound of the formula

<img file="ES2197124T3_D0030.tif" />

(XXX) (Propamocarb) and / or (30) the pyridinimine of the formula

<img file="ES2197124T3_D0031.tif" />

and / or (31) the thiazolecarboxamide of the formula

<img file="ES2197124T3_D0032.tif" />

and / or (32) the sulfonamide of the formula

IS 2 197 124 T3

<img file="ES2197124T3_D0033.tif" />

and / or (33) the compound of the formula and / or

<img file="ES2197124T3_D0034.tif" />

(34) the compound of the formula

<img file="ES2197124T3_D0035.tif" />

ES 2 197 124 T3 (XXXVII) (Thiram) and / or (36) the diamide of the formula

<img file="ES2197124T3_D0036.tif" />

and / or (37) the methoxyacrylate derivative of the formula

<img file="ES2197124T3_D0037.tif" />

and / or (38) the quinoline derivative of the formula

<img file="ES2197124T3_D0038.tif" />

and / or (39) of the phenylamide derivative of the formula

<img file="ES2197124T3_D0039.tif" />

ES 2 197 124 T3 and / or (40) the phenylamide derivative of the formula

<img file="ES2197124T3_D0040.tif" />

and / or (41) the dicarboxime derivative of the formula

<img file="ES2197124T3_D0041.tif" />

II

H — P — OH and / or (42) the phosphoric acid of the formula o

(XXXXIII)

OH (phosphoric acid) and / or (43) the pyrrole derivative of the formula

IS 2 197 124 T3

<img file="ES2197124T3_D0042.tif" />

and / or (44) The phenylcarbonate of the formula

<img file="ES2197124T3_D0043.tif" />

and / or (45) the copper compound a) copper oxychloride (XXXXVIa) b) copper hydroxide (XXXXVIb) (46) the imidazole derivative of the formula

<img file="ES2197124T3_D0044.tif" />

and / or (47) a triazole derivative of the formula

ES 2 197 124 T3 and / or

b) and / or

c)

<img file="ES2197124T3_D0045.tif" />

<img file="ES2197124T3_D0046.tif" />

me

d) and / or

and)

<img file="ES2197124T3_D0047.tif" />

IS 2 197 124 T3

<img file="ES2197124T3_D0048.tif" />

<img file="ES2197124T3_D0049.tif" />

<img file="ES2197124T3_D0050.tif" />

IS 2 197 124 T3

<img file="ES2197124T3_D0051.tif" />

and / or (48) a compound of the general formula

<img file="ES2197124T3_D0052.tif" />

in which

R¹ means phenyl unsubstituted or substituted by fluorine, by chlorine, by bromine, by methyl or by ethyl, 2-naphthyl, 1,2,3,4-tetrahydronaphthyl or indanyl, and / or (49) N-methyl-2- (methoxyimino ) -2- [2 - ([1- (3-trifluoro-methyl phenyl) ethoxy] iminomethyl) -phenyl] acetamide of the formula

<img file="ES2197124T3_D0053.tif" />

and / or (50) 2,4-dihydro-5-methoxy-2-methyl-4- [2 - ([([1- (3-trifluoromethylphenyl) ethylidene] amino) -oxy] methyl) phenyl] - 3H- 1,2,4-triazol-3-one of the formula

<img file="ES2197124T3_D0054.tif" />

and / or (51) the compound of the formula

IS 2 197 124 T3

<img file="ES2197124T3_D0055.tif" />

they have very good fungicidal properties.

Surprisingly, the fungicidal effect of the active compound combinations according to the invention is substantially greater than the sum of the effects of the individual active compounds. Therefore, a real, unpredictable synergistic effect is presented and not just a complement to the effects.

From the structural formula of the active product of formula (I) it can be seen that the compound shows two asymmetrically substituted carbon atoms. The product can therefore be in the form of a mixture of various isomers or else in the form of the individual isomers.

The preferred compounds of formula (I) are compounds in which the amino acid part is formed by i-propyloxycarbonyl-L-valine and the fluorobenzothiazole-ethylamine part is racemic, especially however it has the (R) configuration .

Formula (II) encompasses the compounds

1- (4-chloro-phenoxy) -3,3-dimethyl-1- (1,2,4-triazol-1-yl) -butan-2-one of the formula

<img file="ES2197124T3_D0056.tif" />

1- (4-chloro-phenoxy) -3,3-dimethyl-1- (1,2,4-triazol-1-yl) -butan-2-ol of the formula

<img file="ES2197124T3_D0057.tif" />

^Y

1- (4-phenyl-phenoxy) -3,3-dimethyl-1- (1,2,4-triazol-1-yl) -butan-2-ol of the formula

<img file="ES2197124T3_D0058.tif" />

Formula (IV) encompasses the aniline derivatives of the formulas

IS 2 197 124 T3

<img file="ES2197124T3_D0059.tif" />

From the structural formula of the active product of formula (V) it can be seen that the compound has three asymmetrically substituted carbon atoms. The product can therefore be present as a mixture of the various isomers as well as as a single component. Compounds are preferred

N- (R) - [1- (4-chloro-phenyl) -ethyl] - (1S) -2,2-dichloro-1-ethyl-3t-methyl-1R- cyclopropanecarboxyamide of the formula

<img file="ES2197124T3_D0060.tif" />

^Y

N- (R) - [1- (4-chloro-phenyl) -ethyl] - (1R) -2,2-dichloro-1-ethyl-3t-methyl-1R- cyclopropanecarboxamide of the formula

<img file="ES2197124T3_D0061.tif" />

The formula (VII) encompasses the compounds (VIIa) Me = Zn (Zineb) (VIIb) Me = Mn (Maneb) and (VIIc) mixture of (VIIa) and (VIIb) (Mancozeb).

The formula (XVI) encompasses the compounds (XVIa) R² = CH3 (Pyrimethanil) and (XVIb) R² = - (cyprodinyl) (XVIc) R²= -ChC-CH₃ (Mepanipyrim)

The compound of formula (XVII) can be presented as methyl N- (2,6-dimethylphenyl) -N- (methoxyacetyl) -DLalaninate (Metalaxyl, XVIIa) or comomethyl N- (2,6-dimethylphenyl) -N- (methoxyacetyl ) -D-alaninate (Metalaxyl-M, XVIIb).

The hydroxyethyl-triazole derivative of the formula (XXI) can be present in the "thiono" form of the formula

IS 2 197 124 T3

<img file="ES2197124T3_D0062.tif" />

or in the tautomeric "mercapto" form of the formula

<img file="ES2197124T3_D0063.tif" />

For simplicity's sake, only the “thiono” form will always be indicated.

The guanidine derivative of the formula (XXV) is constituted by a mixture of substances with the common name of Guazatine.

It can be seen from the structural formula of the active compounds of formula (XXXXIX) that the compounds can be present as E or Z isomers. The product can therefore be present as a mixture of several isomers or also in the form of a single isomer. Compounds of the formula (XXXXIX) are preferred, in which the compounds of the formula (XXXXIX) are present as E isomers. Compounds of the formulas

<img file="ES2197124T3_D0064.tif" />

<img file="ES2197124T3_D0065.tif" />

IS 2 197 124 T3

<img file="ES2197124T3_D0066.tif" />

<img file="ES2197124T3_D0067.tif" />

<img file="ES2197124T3_D0068.tif" />

<img file="ES2197124T3_D0069.tif" />

and its isomers.

As mixing components of the compounds of the formula (I), the following active ingredients are particularly preferred:

(3) Tolylfluanid (IVb), (5) Propineb (VI), (6) Mancozeb (VIIc), (7) Fenhexamid (VIII), (8) Iprovalicarb (VIII), (11) Azoxystrobin (XII), (12 ) Trifloxystrobin (XIII), (13) Compound of formula (XIV),

ES 2 197 124 T3 (18) Folpet (XIX), (20) Compounds of the formula (XXI), (26) Compounds of the formula (XXVII), (27) Compounds of the formula (XXVIII), (28) Chlorothalonil (XXIX), (30) Fluazinam (XXXI), and (45) Copper compounds

a) Copper oxychloride (XXXXVIa)

b) Copper hydroxide (XXXXVIb).

The components present in the active compound combinations according to the invention, in addition to a halogenobenzimidazole of the formula (XXVII), are also known.

In particular, the active products are described in the following publications:

(1) Compounds of formula (II)

DE-A 22 01 063! 33 DE-A 23 24 010.

(2) Compounds of formula (III)

EP-A-0 040 345 (3) Compounds of formula (IV)

Pesticide Manual, 9th, Ed. (1991), pages 249 and 827.

(4) Compounds of the formula (V) and their individual derivatives EP-A 0 341 475 (5) Compounds of the formula (VI)

Pesticide Manual, 9th, Ed. (1991), page 726.

(6) Compounds of formula (VII)

Pesticide Manual, 9th, Ed. (1991), page 529, 531 and 866.

(7) Compounds of formula (VIII)

EP-A 0 339 418.

(8) Compounds of formula (IX)

EP-A 0 472 996.

(9) Compounds of formula (X)

EP-A 0 313 512.

(10) Compounds of formula (XI)

EP-A 0 281 842.

(11) Compounds of formula (XII)

EP-A 0 382 375.

(12) Compounds of formula (XIII)

IS 2 197 124 T3

EP-A 460 575.

(13) Compounds of formula (XIV)

DE-A 196 02 095 (14) Compounds of formula (XV)

Pesticide Manual, 9th, Ed. (1991), page 206.

(15) Compounds of formula (XVI)

EP-A 0 270 111 EP-A 0 310 550.

(16) Compounds of formula (XVII)

Pesticide Manual, 9th, Ed. (1991), page 554.

(17) Compounds of formula (XVIII)

EP-A 0 219 756.

(18) Compounds of formula (XIX)

Pesticide Manual, 9th, Ed. (1991), page 431.

(19) Compounds of formula (XX)

Pesticide Manual, 9th, Ed. (1991), page 443.

(20) Compounds of formula (XXI)

WO 96-16048.

(21) Compounds of formula (XXII)

Pesticide Manual, 9th, Ed. (1991), page 491.

(22) Compounds of the formula (XXIII)

EP-A 0 393 911.

(23) Compounds of the formula (XXIV)

EP-A 0 600 629.

(24) Substance of the formula (XXV)

Pesticide Manual, 9th, Ed. (1991), page 461.

(25) Compounds of the formula (XXVI)

Pesticide Manual, 9th, Ed. (1991), page 654.

(26) Compounds of the formula (XXVII)

WO 97-06171.

(27) Compounds of the formula (XXVIII) DE-A1-196 46 407, EP-B-0 712 396.

(28) Compounds of the formula (XXIX)

US 3 290 353.

ES 2 197 124 T3 (29) Compounds of formula (XXX) DE-A-156 7169.

(30) Compounds of the formula (XXXI) EP-A-0 031 257.

(31) Compounds of the formula (XXXII) EP-A-0 639 547.

(32) Compounds of the formula (XXXIII) EP-A-0 298 196.

(33) Compounds of the formula (XXXIV) EP-A-600 629.

(34) Compounds of the formula (XXXV) DE-A-2 149 923.

(35) Compounds of the formula (XXXVI) DE-A-2 012 656.

(36) Compounds of the formula (XXXVII) US 1,972,961.

(37) Compounds of the formula (XXXVIII) EP-A-326 330.

(38) Compounds of the formula (XXXIX) EP-A 278 595.

(39) Compounds of the formula (XXXX) DE-A-3 030 026.

(40) Compounds of the formula (XXXXI) DE-A-2 903 612.

(41) Compounds of the formula (XXXXII) US-2 553 770.

(42) Compounds of the formula (XXXXIII) known and commercially available.

(43) Compounds of the formula (XXXXIV) EP-A-206 999 (44) Compound of the formula (XXXXV) EP-A-78 663.

(45)

a) Compound of the formula (XXXXVIa)

ES 2 197 124 T3 known and commercially available.

c) Compound of the formula (XXXXVIb) known and commercially available.

(46) Compound of the formula (XXXXVII)

DE-A-2 429 523.

(47)

a) Compound of the formula (XXXXVIIIa)

EP-A-112 284.

b) Compound of the formula (XXXXVIIIb)

DE-A-3 042 303.

c) Compound of the formula (XXXXVIIIc)

DE-A-3 406 993.

d) Compound of the formula (XXXXVIIId)

EP-A-68 813.

e) Compound of the formula (XXXXVIIIe)

DE-A-2551560.

f) Compound of the formula (XXXXVIIIf)

EP-A-145 294.

g) Compound of the formula (XXXXVIIIg)

DE-A-3 721 786.

h) Compound of the formula (XXXXVIIIh)

EP-A-234 242.

(48) Compound of the formula (XXXXIX)

WO 96/23763.

(49) Compound of the formula (XXXXX)

EP-A-596 254.

(50) Compound of the formula (XXXXXI)

WO 98/23155.

(51) Compound of the formula (XXXXXII)

EP-A-569 384.

The active compound combinations according to the invention contain, in addition to an active compound of the formula (I) at least one active compound of the compounds of groups (1) to (51). In addition, they can also contain other mixing components with fungicidal activity.

When the active compounds are present in the active compound combinations according to the invention in certain proportions by weight, the synergistic effect is particularly clear. However, the proportions by weight of the active ingredients in the active ingredient combinations can vary within relatively wide limits. In general they correspond to one part by weight of the active compound of formula (I)

ES 2 197 124 T3 0.1 to 50 parts by weight, preferably 0.2 to 20 parts by weight of active compound from group (1), 0.1 to 50 parts by weight, preferably 0.2 to 20 parts by weight of active compound from group (2), from 1 to 150 parts by weight, preferably from 1 to 100 parts by weight of active compound from group (3), from 0.1 to 10 parts by weight, preferably from 0.2 to 5 parts by weight of active compound from group (4), from 1 to 150 parts by weight, preferably from 5 to 100 parts by weight of active compound from group (5), from 1 to 150 parts by weight, preferably from 5 to 100 parts by weight of active compound from group (6), from 0.1 to 50 parts by weight weight, preferably 1 to 20 parts by weight of active compound of group (7), 0.1 to 50 parts by weight, preferably 0.2 to 20 parts by weight of active compound of group (8), 0 , 02 up to 50 parts by weight, preferably from 0.2 to 10 parts by weight of active compound from group (9), from 0.1 to 50 parts by weight, preferably from 0.2 to 20 parts by weight of active compound from group (10), from 0 , 1 to 50 parts by weight, preferably 0.2 to 20 parts by weight of active compound from group (11), 0.1 to 50 parts by weight, preferably 0.2 to 20 parts by weight of active compound from group (12), from 0.1 to 50 parts by weight, preferably from 0.2 to 20 parts by weight of active compound from group (13), from 0.1 to 50 parts by weight, preferably from 0.2 to 20 parts by weight of active compound from group (14), from 0 2 to 50 parts by weight, preferably 1 to 20 parts by weight of active compound from group (15), 0.1 to 50 parts by weight, preferably 0.2 to 20 parts by weight of active compound from group (16), from 0.1 to 50 parts by weight, preferably from 0.2 to 20 parts by weight of active compound from group (17), from 1 to 150 parts by weight, preferably from 5 to 100 parts by weight of active compound from group (18), from 0.1 to 150 parts by weight, preferably from 1 to 100 parts by weight of active compound from group (19), from 0.02 to 50 parts by weight, preferably from 0.2 to 10 parts by weight of active compound from group (20), from 0.05 to 20 parts by weight, preferably from 0.1 to 10 parts by weight of active compound from group (21), from 0.1 to 50 parts by weight, preferably from 0.2 to 20 parts by weight of active compound from group (22), from 0 1 to 50 parts by weight, preferably 0.2 to 20 parts by weight of active compound from group (23), 0.01 to 150 parts by weight, preferably 1 to 100 parts by weight of active compound from group (24), 0.1 to 50 parts by weight, preferably from 0.2 to 20 parts by weight of active compound from group (25), from 0.1 to 50 parts by weight, preferably from 0.2 to 20 parts by weight of active compound from group (26), from 0 , 1 to 50 parts by weight, preferably 0.2 to 20 parts by weight of active compound of group (27), 1 to 150 parts by weight, preferably 5 to 100 parts by weight of active compound of group (28 ), from 1 to 150 parts by weight, preferably from 5 to 100 parts by weight of active compound from group (29), from 0.1 to 50 parts by weight, preferably from 0.2 to 20 parts by weight of active compound from group (30), from 0.1 up to 50 parts by weight, preferably 0.2 to 20 parts by weight of active compound from group (31), 0.1 to 50 parts by weight, preferably 0.2 to 20 parts by weight of active compound from group (32), 0.1 to 50 parts by weight, preferably from 0.2 to 20 parts by weight of active compound from group (33), from 0.1 to 50 parts by weight, preferably from 1 to 20 parts by weight of active compound from group (34),

ES 2 197 124 T3 0.1 to 50 parts by weight, preferably 1 to 10 parts by weight of active compound from group (35), 1 to 150 parts by weight, preferably 5 to 100 parts by weight of product active compound from group (36), from 0.1 to 50 parts by weight, preferably from 0.2 to 20 parts by weight of active compound from group (37), from 0.1 to 50 parts by weight, preferably from 0, 2 to 20 parts by weight of active compound from group (38), from 0.1 to 50 parts by weight, preferably from 0.2 to 20 parts by weight of active compound from group (39), from 0.1 to 50 parts by weight, preferably from 0.2 to 20 parts by weight of active compound from group (40), from 1 up to 150 parts by weight, preferably from 5 to 100 parts by weight of active compound from group (41), from 1 to 150 parts by weight, preferably from 5 to 100 parts by weight of active compound from group (42), from 0 , 1 to 50 parts by weight, preferably 1 to 20 parts by weight of active compound from group (43), 0.1 to 50 parts by weight, preferably 1 to 20 parts by weight of active compound from group (44), 1 to 150 parts in weight, preferably 5 to 100 parts by weight of active compound of group (45a), 1 to 150 parts by weight, preferably 5 to 100 parts by weight of active compound of group (45b), 0.1 to 50 parts by weight, preferably from 0.2 to 20 parts by weight of active compound from group (46), from 0.1 to 50 parts by weight, preferably from 0.2 to 20 parts by weight of active compound from group (47a), from 0 1 to 50 parts by weight, preferably 0.2 to 20 parts by weight of active compound from group (47b), 0.1 to 50 parts by weight, preferably 0.2 to 20 parts by weight of active compound from group (47c), 0.1 to 50 parts by weight, preferably from 0.2 to 20 parts by weight of active compound from group (47d), from 0.1 to 50 parts by weight, preferably from 0.2 to 20 parts by weight of active compound from group (47e), from 0 1 to 50 parts by weight, preferably 0.2 to 20 parts by weight of active compound from group (47f), 0.1 to 50 parts by weight, preferably 0.2 to 20 parts by weight of active compound from group (47g), 0.1 to 50 parts by weight, preferably from 0.2 to 20 parts by weight of active compound from group (47h), from 0.1 to 50 parts by weight, preferably from 0.2 to 20 parts by weight of active compound from group (48), from 0 1 to 50 parts by weight, preferably 0.2 to 20 parts by weight of active compound from group (49), 0.1 to 50 parts by weight, preferably 0.2 to 20 parts by weight of active compound from group (50), from 0.1 to 50 parts by weight, preferably 0.2 to 20 parts by weight of active compound from group (51),

The active compound combinations according to the invention have very good fungicidal properties and can be used to control phytopathogenic fungi, such as plasmodiophoromycetes, oomycetes, chytridiomycetes, zygomycetes, ascomycetes, basidiomycetes, deuteromycetes, etc.

The active compound combinations according to the invention are particularly suitable for combating Phytophthora infestans and Plasmopara viticola.

The good compatibility with plants of the active compound combinations at the concentrations necessary for the control of plant diseases allows a treatment of the aerial parts of plants, of seedlings and seeds and of the soil. The active compound combinations according to the invention can be used for application to leaves or else as disinfectants.

The active compound combinations according to the invention are also suitable for increasing crop yields. They also have low toxicity and have good compatibility with plants.

All plants and plant parts can be treated according to the invention. By plants it is meant herein all plants and plant populations, such as desired and unwanted wild plants (including naturally occurring crop plants). Crop plants can be plants that can be obtained through

ES 2 197 124 T3 conventional methods and cultivation and optimization or by means of biotechnological and genetic engineering methods, including transgenic plants and including plant varieties that may or may not be protected by means of the right of protection of vegetable varieties. By plant parts, all the aerial and subterranean parts and organs of the plants should be understood, such as shoots, leaves, flowers and roots, being able to indicate in an exemplary way leaves, needles, stems, trunks, flowers, bodies of fruits, fruits and seeds as well as roots, tubers and rhizomes. The plant parts also include crops as well as vegetative and generative propagating material, for example seedlings, tubers, rhizomes, layers and seeds.

The treatment according to the invention of plants and plant parts with the active ingredients is carried out according to customary treatment methods, for example by dipping, spraying, evaporating, misting, spraying, brushing and, in the case of the material reproduction, especially in the case of seeds, also by coating with one or more layers.

The active compound formulations according to the invention can be transformed into customary formulations, such as solutions, emulsions, suspensions, powders, foams, pastes, granules, aerosols, microencapsulated in polymeric materials and seed coating compositions, as well as ULV formulations.

These formulations are prepared in a known manner, for example by mixing the active compounds with extenders, that is to say with liquid solvents, gases liquefied under pressure and / or solid excipients, if necessary with the use of surfactants, that is to say emulsifiers and / or dispersants and / or foam generating means. (When water is used as an extender, organic solvents can be used, for example, as auxiliary solvents. (As liquid solvents, the following preferably come into consideration: aromatic hydrocarbons, such as xylene, toluene or alkylnaphthalene, chlorinated aromatic hydrocarbons and chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chloroethylenes or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, for example petroleum fractions , alcohols such as butanol or glycol, as well as their ethers and esters, ketones, such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, or strongly polar solvents, such as dimethylformamide and dimethylsulfoxide as well as water; by liquefied gaseous extenders or excipients are meant those liquids that are gaseous at normal temperature and normal pressure, for example propellant gases for aerosols, such as halogenated hydrocarbons as well as butane, propane, nitrogen and carbon dioxide; as solid excipients come into consideration: for example ground natural minerals, such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and ground synthetic minerals, such as highly dispersed silicic acid, aluminum oxide and silicates; as solid excipients for granules come into consideration: for example broken and fractionated natural minerals, such as calcite, marble, pumice stone, sepiolite and dolomite, as well as synthetic granules of inorganic and organic flours and granules of organic material, such as sawdust , coconut shells, corn husks and tobacco stalks; suitable emulsifiers and / or foaming agents are: for example, non-ionogenic and anionic emulsifiers, such as polyoxyethylenated esters of fatty acids, polyoxyethylenated ethers of fatty alcohols, for example alkylaryl polyglycol ether, alkylsulfonates, alkyl sulfates, arylsulfonates, as well as albumin hydrolysates; suitable dispersants are: for example, lignin sulphite liquors and methylcellulose.

Adhesives such as carboxymethyl cellulose, natural and synthetic powdered, granulable or latex polymers such as gum arabic, polyvinyl alcohol, polyvinyl acetate, as well as natural phospholipids such as cephalin and lecithin, and synthetic phospholipids can be used in the formulations. Other additives can be mineral and vegetable oils.

Dyes, such as inorganic pigments, for example iron oxide, titanium oxide, Prussian blue, and organic dyes, such as alizarin, azo and metallic phthalocyanine dyes, as well as trace nutrients, such as iron salts, manganese can be used. , boron, copper, cobalt, molybdenum and zinc.

The formulations generally contain between 0.1 and 95% by weight, preferably between 0.5 and 90% of active compound.

The active compound combinations according to the invention can be used as such or in their formulations also in admixture with other known fungicides, bactericides, acaricides, nematicides or insecticides to thereby broaden the spectrum of activity or to prevent the development of resistance. In many cases, synergistic effects occur, that is to say that the activity of the mixture is greater than the activity of the individual components.

A mixture with other active ingredients, such as herbicides or with fertilizers and growth regulators, is also possible.

The active compound combinations can be used as such in the form of their formulations or of the application forms prepared from the above, such as ready-to-use solutions, suspensions, injectable powders, pastes, soluble powders, dusting agents and granules. . The use is carried out in the usual way, for example by watering, spraying, dusting, scattering, dusting, dry disinfection, wet disinfection, immersion disinfection, suspension disinfection or incrustation.

(When the active compound combinations according to the invention are used, the application rates can be

ES 2 197 124 T3 vary, depending on the type of application, within wide limits. When plant parts are treated, the concentrations in the active compound combination are generally between 0.1 and 10,000 g / ha, preferably between 10 and 1,000 g / ha. In the case of seed treatment, the application rates in combination of active ingredients are generally between 09.001 and 50 g per kilogram of seeds, preferably between 0.01 and 10 g per kilogram of seeds. In the case of soil treatment, the application rates in combination of active ingredients are generally between 0.1 and 10,000 g / ha, preferably between 1 and 5,000 g / ha.

The good fungicidal action of the active compound combinations according to the invention is apparent from the following examples. While the individual active ingredients have weak points in terms of the fungicidal effect, the combinations show an effect that goes beyond a simple sum of the effects.

The active compound combinations according to the invention can be applied to the plants before and after emergence, that is to say according to the pre-emergence process and in the post-emergence process. However, they can also be incorporated into the ground before proceeding to sowing.

There is a synergistic effect in fungicides provided that the fungicidal effect of the combination of active ingredients is greater than that of the active ingredients applied individually.

The expected effect for a given combination of two active products can be calculated according to SR Colby ("Calculating Synergistic and Antagonistic Responses of Herbicide Combinations", Weeds 15, pages 20-22, 1967) as follows:

Yes

X means is the degree of activity when the active product A is used with an application amount mg ​​/ ha

Y means is the degree of activity when active product B is used with an application amount ng / ha and

E means the degree of activity when the active products A and B are used with the application amounts myng / ha, then

E = X + Y - (X * Y / 100).

In this case, the degree of activity is determined in%. A degree of activity of 0% corresponds to that of the controls, while a degree of activity of 100% means that no attack is observed.

If the actual fungicidal effect is greater than the calculated one, the combination will be over-additive, that is, a synergistic effect is present. In this case, the degree of activity actually observed must be greater than the value calculated by means of the formula indicated above for the degree of activity (E) to be expected.

The invention is explained by means of the following examples. However the invention is not limited to these examples.

Example 1

Trial with Phytophthora (tomato / protector

Solvent: 47 Parts by weight of acetone.

Emulsifier: 3 Parts by weight of alkylaryl polyglycol ether.

To obtain a suitable active ingredient preparation, 1 part by weight of active ingredient or combination of active ingredients is mixed with the indicated amounts of solvent and emulsifier and the concentrate is diluted with water to the desired concentration or a formulation is diluted of active product or of combination of active products, usual in the trade, with water up to the desired concentration.

To test the protective activity, young plants are sprayed with the active product preparation in the indicated application amount. After the spray coating has dried, the plants are inoculated with an aqueous spore suspension of Phytophthora infestans. The plants are then placed in an incubation cabin at approximately 20 ° C and with an air humidity of 100%.

The evaluation of the attack by the disease is carried out 3 days after inoculation. In this case 0% means a degree of activity, which corresponds to that of the controls, while a degree of activity of 100% means that no attack is observed.

The effect found of the combination of active ingredients according to the invention is greater than the calculated effect,

ES 2 197 124 T3, that is to say that there is a synergistic effect. The combination consisting of the compound of the formula (I) and the halogen-benzimidazole of the formula No. XXVII has, with a mixing ratio of 1: 1 and with an application rate of 0.1 g / ha, a 73% real activity level. The expected value calculated according to Colby's formula, 63%, is significantly lower

TABLE 1

Assay with Phytophthora (tomato) / protector

<td>Active product Known</td><td>Amount of active product applied in g / ha</td><td>Activity level on %</td>

<td>Compound of the formula (XXVII) XXXl · " XX</td><td> 0,1</td><td> 30</td>

<td>Compound of the formula (1) H, (T -CH- CH, O³ Y ³ N-2 ZH-^FYOUNG / X^H or ch₃</td><td> 0,1</td><td> 47</td>

Mixture according to the invention:

<td>Active product</td><td>Proportion of mix</td><td>Amount of application of active product in g / ha</td><td>Actual activity level</td><td>Expected value, calculated with Colby's formula</td>

<td>XXVII + 1</td><td></td><td> 0,1 + 0,1</td><td></td><td> 63</td>

IS 2 197 124 T3

TABLE 2

Assay with Phytophthora (tomato) / protector

<td colspan="3">Active product</td><td rowspan="2">Amount of active product applied in g / ha</td><td rowspan="2">Activity level on %</td>

<td>C</td><td colspan="2">unknown</td>

<td colspan="2">Compound of formula (I)</td><td></td><td> 1</td><td> 47</td>

<td>H, Ck</td><td>.CH,</td><td></td><td></td><td></td>

<td>CH, 9</td><td> &lt; ³ N-</td><td>TO // ^F</td><td></td><td></td>

<td rowspan="2">H.cAtAjj-</td><td>Η I &lt;/ N- * r'1 ηρ</td><td>s^z</td><td></td><td></td>

<td>0 ch₃</td><td></td><td></td><td></td>

<td>Propineb (VI)</td><td></td><td></td><td> 20</td><td> 19</td>

<td>s</td><td> 9^H3</td><td>s</td><td></td><td></td>

<td>II</td><td>T</td><td>II</td><td></td><td></td>

<td>- [Zn — S — C — NH</td><td>—CH — CH — NH</td><td>-c-st-</td><td></td><td></td>

<td>n&gt; = 1</td><td colspan="2">(Propineb)</td><td></td><td></td>

Mixture according to the invention:

<td>Active product</td><td>Proportion of mix</td><td>Amount of application of active product in g / ha</td><td>Actual activity level</td><td>Expected value, calculated with Colby's formula</td>

<td>(1) + Propineb (VI)</td><td> 1:20</td><td> 0,1 + 20</td><td> 94</td><td> 57</td>

IS 2 197 124 T3

TABLE 3

Assay with Phytophthora (tomato) Zprotector

<td colspan="2">Active product Known</td><td>Amount of active product applied in g / ha</td><td>Activity level on %</td>

<td>Compound of the formula (1)</td><td></td><td> 1</td><td> 47</td>

<td>H, C-, / CH,</td><td>\ _p</td><td></td><td></td>

<td>CH, O³ ’</td><td>N -A</td><td></td><td></td>

<td rowspan="2">/ k JU - © χΝχΛχ ^H3^C ° ü'lf I^H 0 CH</td><td>J]</td><td></td><td></td>

<td> 3</td><td></td><td></td>

<td></td><td></td><td> 20</td><td> 12</td>

<td>Chlorothalonil (XXIX)</td><td></td><td></td><td></td>

<td>CN I</td><td></td><td></td><td></td>

<td>CL</td><td rowspan="2">/ Cl</td><td></td><td></td>

<td></td><td></td><td></td>

<td></td><td rowspan="2">^ CN</td><td></td><td></td>

<td></td><td></td><td></td>

Mixture according to the invention:

<td>Active product</td><td>Proportion of mix</td><td>Amount of application of active product in g / ha</td><td>Actual activity level</td><td>Expected value, calculated with Colby's formula</td>

<td>(1) + Chlorothalonil (XXIX)</td><td> 1:20</td><td> 1 + 20</td><td> } ⁸⁴</td><td> 53</td>

IS 2 197 124 T3

TABLE 4

Assay with Phytophthora (tomato) Zprotector

<td>Active product Known</td><td>Amount of active product applied in g / ha</td><td>Activity level on %</td>

<td>Compound of the formula (1)</td><td> 1</td><td> 47</td>

<td>H, C. .CH, CH, O^{3 3} NA # -^F0 ch₃</td><td></td><td></td>

<td>Dichlofluanid (IVa)</td><td> 20</td><td> 5</td>

<td>An (^{S_CC, /}^ SO_rN &lt;CH₃)₂</td><td></td><td></td>

Mixture according to the invention:

<td>Active product</td><td>Proportion of mix</td><td>Amount of application of active product in g / ha</td><td>Actual activity level</td><td>Expected value, calculated with the Coiby formula</td>

<td>(I) 4-</td><td>f 1:20</td><td> 1 +</td><td>X</td><td> 50</td>

<td>Dichlofluanid (IVa)</td><td>J</td><td> 20</td><td>r 87</td><td></td>

IS 2 197 124 T3

TABLE 5

Assay with Phytophthora (tomato) Zprotector

<td colspan="2">Active product Known</td><td>Amount of active product applied in g / ha</td><td>Activity level on %</td>

<td>Compound of formula (I)</td><td></td><td> 1</td><td> 47</td>

<td>H, C. .CH,</td><td>-Z \ F</td><td></td><td></td>

<td>CH, O^{3 3} N</td><td></td><td></td><td></td>

<td>^H3^C o N 1 or ch₃</td><td>s^z</td><td></td><td></td>

<td></td><td></td><td> 20</td><td> 21</td>

<td>Tolylfluanid (IVb)</td><td></td><td></td><td></td>

<td>H, c3y &lt;^s\ = / so_r</td><td>CCIjF NtCH, ^</td><td></td><td></td>

Mixture according to the invention:

<td>Active product</td><td>Proportion of mix</td><td>Amount of application of active product in g / ha</td><td>Actual activity level</td><td>Expected value, calculated with Colby's formula</td>

<td>(I) + Tolylfluanid (IVa)</td><td> 1:20</td><td> 1 + 20</td><td> } ⁹⁵</td><td> 58</td>

IS 2 197 124 T3

TABLE 6

Assay with Phytophthora (tomato) / protector

<td colspan="2">Active product Known</td><td>Amount of active product applied in g / ha</td><td>Activity level on %</td>

<td colspan="2">Compound of the formula (1)</td><td> ]</td><td> 47</td>

<td>H, C. CH, O³ Y i ³ X 1 Η, Ο Ο '' © ·³ H</td><td>^{CHs f}β .Λ Μ Or ch₃</td><td></td><td></td>

<td></td><td></td><td rowspan="2"> 20</td><td rowspan="2"> 0</td>

<td>Folpet (XIX)</td><td>j?</td>

<td>α</td><td>/ V or</td><td></td><td></td>

Mixture according to the invention:

<td>Active product</td><td>Proportion of mix</td><td>Amount of application of active product in g / ha</td><td>Actual activity level</td><td>Expected value, calculated with Colby's formula</td>

<td>(I) 4-</td><td>f 1:20</td><td> 1 4-</td><td></td><td> 47</td>

<td>Folpet (XIX)</td><td>J</td><td> 20</td><td> / ⁹⁵</td><td></td>

IS 2 197 124 T3

TABLE 7

Assay with Phytophthora (tomato) / protector

<td>Active product Known</td><td>Amount of active product applied in g / ha</td><td>Activity level on %</td>

<td>Compound of the formula (1)</td><td> 1</td><td> 39</td>

<td>λλΙλλ ^^h&gt;^c ° κ if τ 0 CH,</td><td></td><td></td>

<td>Mancozeb (VIlc)</td><td> 20</td><td> 28</td>

Mixture according to the invention:

<td>Active product</td><td>Proportion of mix</td><td>Amount of application of active product in g / ha</td><td>Actual activity level</td><td>Expected value, calculated with Colby's formula</td>

<td>(1) + Mancozeb (VIlc)</td><td> 1:20</td><td> 1 + 20</td><td> 68</td><td> 56</td>

TABLE 8

Assay with Phytophthora (tomato) / protector

<td>Active product Known</td><td>Amount of active product applied in g / ha</td><td>Activity level on %</td>

<td>Compound of formula (I)</td><td> 1</td><td> 47</td>

<td>H_toC ^ © Η, f 0 ch₃</td><td></td><td></td>

<td>Bitertanol (11c)</td><td> 10</td><td> 4</td>

IS 2 197 124 T3

Mixture according to the invention:

<td>Active product</td><td>Proportion of mix</td><td>Amount of application of active product in g / ha</td><td>Actual activity level</td><td>Expected value, calculated with Colby's formula</td>

<td>(1) + Bitertanol (lie)</td><td> 1:10</td><td> 1 + 10</td><td>b</td><td> 49</td>

TABLE 9

Assay with Phytophthora (tomato) / protector

<td colspan="2">Active product Known</td><td>Amount of active product applied in g / ha</td><td>Activity level on %</td>

<td>Compound of formula (I)</td><td></td><td> 1</td><td> 47</td>

<td>H, C. .CH,</td><td>-Z Λ Γ</td><td></td><td></td>

<td>CH_to OR³ 'Ν'</td><td></td><td></td><td></td>

<td>^H,^c ° Η © Γ 1 or ch₃</td><td>'S^Z</td><td></td><td></td>

<td>Tebuconazole (III) &lt;</td><td></td><td> 10</td><td> 5</td>

<td>Cl — H-CH-CH, -!</td><td>-C (CH₃)₃h₂-N</td><td></td><td></td>

Mixture according to the invention:

<td>Active product</td><td>Proportion of mix</td><td>Amount of application of active product in g / ha</td><td>Actual activity level</td><td>Expected value, calculated with Colby's formula</td>

<td>(1) + Tebuconazole (ΠΙ)</td><td> 1:10</td><td> 1 + 10</td><td>b</td><td> 50</td>

IS 2 197 124 T3

TABLE 10

Assay with Phytophthora (tomato) / protector

<td>Active product Known</td><td>Amount of active product applied in g / ha</td><td>Activity level on %</td>

<td>Compound of formula (I) CH_to or^BC©-^{CH3 F}^H3^C ° ν © f γ ^s0 ch₃</td><td> 1</td><td> 47</td>

<td>Triadimenol (Ilb) ci — o- &lt;¡: h-ch — C (ch₃)₃A &lt;J N—</td><td> 10</td><td> 0</td>

Mixture according to the invention:

<td>Active product</td><td>Proportion of mix</td><td>Amount of application of active product in g / ha</td><td>Actual activity level</td><td>Expected value, calculated with the Coiby formula</td>

<td>(I) + Triadimenol (Hb)</td><td> 1:10</td><td> 1 + 10</td><td> 88</td><td> 47</td>

IS 2 197 124 T3

TABLE 11

Assay with Phytophthora (tomato) / protector

<td>Active product Known</td><td>Amount of active product applied in g / ha</td><td>Activity level on %</td>

<td>Compound of formula (i) H, C ^ ___ CH, ,, F CH, O^{3 N}\\ // ^bAwr or ch₃</td><td> 1</td><td> 47</td>

<td>Imidacloprid (XXII)</td><td> 10</td><td> 0</td>

<td>cr ^ rr n — no₂</td><td></td><td></td>

Mixture according to the invention:

<td>Active product</td><td>Proportion of mix</td><td>Amount of application of active product in g / ha</td><td>Actual activity level</td><td>Expected value, calculated with Colby's formula</td>

<td>(I) + imidacloprid (XXII)</td><td> 1:10</td><td>1 η- ΙΟ</td><td> } ’·</td><td> 47</td>

IS 2 197 124 T3

TABLE 12

Assay with Phytophthora (tomato) / protector

<td>Active product</td><td>Applied amount of</td><td>Activity level</td>

<td>Known</td><td>active product in g / ha</td><td>on %</td>

<td>Compound of the formula (1) Γ³ f Ύ *³”. rO^F0 ch₃</td><td> 1</td><td> 47</td>

<td>Compound of the formula (XXI) (20)</td><td> 10</td><td> 2</td>

<td>Cl &gt; _ / OH</td><td></td><td></td>

<td>fycH_F¿V_cl</td><td></td><td></td>

<td>'-' 1 ch₂</td><td></td><td></td>

<td>'L-NH</td><td></td><td></td>

Mixture according to the invention:

<td>Active product</td><td>Proportion of mix</td><td>Amount of application of active product in g / ha</td><td>Actual activity level</td><td>Expected value, calculated with Colby's formula</td>

<td>(I) + (XXI) (20)</td><td> 1:10</td><td> 1 + 10</td><td> } “</td><td> 48</td>

IS 2 197 124 T3

TABLE 13

Assay with Phytophthora (tomato) / protector

<td colspan="2">Active product Known</td><td>Amount of active product applied in g / ha</td><td>Activity level on %</td>

<td colspan="2">Compound of the formula (1)</td><td> 1</td><td> 47</td>

<td>H, C. ?³X HaC ^ O ^ N</td><td> &lt;^CH3or ch₃</td><td></td><td></td>

<td colspan="2">Fenhexamid (VIII)</td><td> 10</td><td> 13</td>

<td>Q (</td><td>1 fí —C — NH — V-OH : h, „) \³ Cl Cl</td><td></td><td></td>

Mixture according to the invention:

<td>Active product</td><td>Proportion of mix</td><td>Amount of application of active product in g / ha</td><td>Actual activity level</td><td>Expected value, calculated with Colby's formula</td>

<td>(I) + Fenhexamid (HIV)</td><td> 1:10</td><td> ] + 10</td><td> 70</td><td> 54</td>

IS 2 197 124 T3

TABLE 14

Assay with Phytophthora (tomato) / protector

<td colspan="3">Active product Known</td><td>Amount of active product applied in g / ha</td><td>Activity level on %</td>

<td>Compound of formula (I)</td><td></td><td></td><td>i</td><td> 47</td>

<td colspan="2">Λ³ X</td><td>'S^Z</td><td></td><td></td>

<td> 0</td><td>ch₃</td><td></td><td></td><td></td>

<td>Carpropamid (V)</td><td></td><td></td><td> 10</td><td> 0</td>

<td>^H\</td><td></td><td></td><td></td><td></td>

<td>^Cl "{Χ</td><td rowspan="2">^ ch₃-β</td><td></td><td></td><td></td>

<td></td><td>fy_c,</td><td></td><td></td>

<td> 1</td><td>h₃c</td><td> \=/</td><td></td><td></td>

Mixture according to the invention:

<td>Active product</td><td>Proportion of mix</td><td>Amount of application of active product in g / ha</td><td>Actual activity level</td><td>Expected value, calculated with Colby's formula</td>

<td>(1) + Carpropamid (V)</td><td> 1:10</td><td> 1 + 10</td><td> 90</td><td> 47</td>

IS 2 197 124 T3

TABLE 15

Assay with Phytophthora (tomato) / protector

<td>Active product Known</td><td>Amount of active product applied in g / ha</td><td>Activity level on %</td>

<td>Compound of the formula (1) H, C- / CH, Ύ⁼⁼\ - f CH, O^{3 3} // ^For ch₃</td><td> ]</td><td> 47</td>

<td>Spiroxamine (XI) (CH ^ cyv⁰© o- \ h_ &lt;^c’^h' C₃H₇-n</td><td> 10</td><td> 0</td>

Mixture according to the invention:

<td>Active product</td><td>Proportion of mix</td><td>Amount of application of active product in g / ha</td><td>Actual activity level</td><td>Expected value, calculated with Colby's formula</td>

<td>(I)</td><td>Λ</td><td> 1</td><td></td><td> 47</td>

<td> +</td><td></td><td> +</td><td>i</td><td></td>

<td>Spiroxamine (XI)</td><td>I 1:10</td><td> 10</td><td>r ee</td><td></td>

IS 2 197 124 T3

TABLE 16

Assay with Phytophthora (tomato) / protector

<td>Active product</td><td></td><td></td><td>Applied amount of</td><td>Activity level</td>

<td>Known</td><td></td><td></td><td>active product in g / ha</td><td>on %</td>

<td>Compound of the formula (1)</td><td></td><td></td><td> 1</td><td> 39</td>

<td>ch₃ or^H3CV^CH3 n Λ Λ AJM^H3^co ñ 1 T or ch₃</td><td>&gt; 's^/</td><td></td><td></td><td></td>

<td>Fluazinam (XXXI)</td><td></td><td></td><td> 10</td><td> 56</td>

<td>Cl^CFs—</td><td>No J</td><td>„Ci</td><td></td><td></td>

<td>N l |</td><td></td><td>cf₃</td><td></td><td></td>

Mixture according to the invention:

<td>Active product</td><td>Proportion of mix</td><td>Amount of application of active product in g / ha</td><td>Actual activity level</td><td>Expected value, calculated with Colby's formula</td>

<td>OR) + Fluazinam (XXXI)</td><td> 1:10</td><td> 1 + 10</td><td> 87</td><td> 73</td>

IS 2 197 124 T3

TABLE 17

Assay with Phytophthora (tomato) / protector

<td>Active product</td><td>Applied amount of</td><td>Activity level</td>

<td>Known</td><td>active product in g / ha</td><td>on %</td>

<td>Compound of the formula (1) / \ __FCH O³ X ³ // ^rTO³A AJUA / ^^h3^c ° n &lt;y Y so ch₃</td><td> 1</td><td> 47</td>

<td>Compound of the formula (XXVIil) (27)</td><td> 1</td><td> 9</td>

<td>fA Άτ ¡γ</td><td></td><td></td>

<td></td><td></td><td></td>

<td>^{CHs F}hsc- '°' 'N-^íY- ^ chs</td><td></td><td></td>

<td>or</td><td></td><td></td>

Mixture according to the invention:

<td>Active product</td><td>Proportion of mix</td><td>Amount of application of active product in g / ha</td><td>Actual activity level</td><td>Expected value, calculated with Colby's formula</td>

<td>(1) + (XXV11) (27)</td><td>²</td><td> 1 + 1</td><td> 72</td><td> 52</td>

IS 2 197 124 T3

TABLE 18

Assay with Phytophthora (tomato) / protector

<td colspan="2">Active product Known</td><td>Amount of active product applied in g / ha</td><td>Activity level on %</td>

<td>Compound of formula (I)</td><td></td><td> 1</td><td> 47</td>

<td>TO³ To Xa.JL_s^h3^{c 0} i or ch₃</td><td></td><td></td><td></td>

<td>Compound of the formula (XIV) (13)</td><td></td><td> 1</td><td> 8</td>

<td></td><td>Ή</td><td></td><td></td>

<td>AXA</td><td>H</td><td></td><td></td>

<td>Cl F _XOR_X TO H_SC^{X x}hT</td><td></td><td></td><td></td>

<td></td><td></td><td></td><td></td>

Mixture according to the invention:

<td>Active product</td><td>Proportion of mix</td><td>Amount of application of active product in g / ha</td><td>Actual activity level</td><td>Expected value, calculated with Coiby's formula</td>

<td>(1) + (XIV) (13)</td><td>μ</td><td> 1 + 1</td><td> }«</td><td> 51</td>

IS 2 197 124 T3

TABLE 19

Assay with Phytophthora (tomato) / protector

<td>Active product Known</td><td>Amount of active product applied in g / ha</td><td>Activity level on %</td>

<td>Formula 1) H, C. .CH,, ._ V⁼⁼\-F V.! Ύ H rYx ^FH₃c2 ^ O '^ N^X©|^^N'Y ^' S^H or ch₃</td><td> 1</td><td> 56</td>

<td>Compound of the formula (XXXXVla) (40) Copper oxychloride</td><td> 50</td><td> 0</td>

Mixture according to the invention:

<td>Active product</td><td>Proportion of mix</td><td>Amount of application of active product in g / ha</td><td>Actual activity level</td><td>Expected value, calculated with Colby's formula</td>

<td>(1) + Copper oxychloride (XXXXVla)</td><td> 1:50</td><td> 1 + 50</td><td> }</td><td> 56</td>

IS 2 197 124 T3

TABLE 20

Assay with Phytophthora (tomato) / protector

<td>Active product Known</td><td>Amount of active product applied in g / ha</td><td>Activity level on %</td>

<td>Formula 1) H, C. , CH, f 0 ch₃</td><td> 1</td><td> 56</td>

<td>Compound formula (XII) (11) Azoxystrobin N ©? Saw</td><td> 1</td><td> 55</td>

<td>° AND © ¡</td><td></td><td></td>

<td></td><td></td><td></td>

<td> 0-0</td><td></td><td></td>

Mixture according to the invention:

<td>Active product</td><td>Proportion of mix</td><td>Amount of application of active product in g / ha</td><td>Actual activity level</td><td>Expected value, calculated with Colby's formula</td>

<td>FORMULA 1) + Azoxystrobin (Xll)</td><td></td><td> 1 + ]</td><td> } “</td><td> 80</td>

IS 2 197 124 T3

TABLE 21

Assay with Phytophthora (tomato) / protector

<td>Active product</td><td>Applied amount of</td><td>Activity level</td>

<td>Known</td><td>active product in g / ha</td><td>on %</td>

<td>Formula (I)</td><td> 1</td><td> 56</td>

<td>HXk.CH, F Λ³ X H, WITH 'Y' and 'S 0 ch₃</td><td></td><td></td>

<td>Compound of the formula (XIII) (12)</td><td> 1</td><td> 0</td>

<td>Trifloxystrobin</td><td></td><td></td>

<td></td><td></td><td></td>

<td></td><td></td><td></td>

<td>_FZ \ Ti^F %</td><td></td><td></td>

<td>Vile</td><td></td><td></td>

<td></td><td></td><td></td>

<td>Ο'λ)</td><td></td><td></td>

<td>ch₃</td><td></td><td></td>

Mixture according to the invention:

<td>Active product</td><td>Proportion of mix</td><td>Amount of application of active product in g / ha</td><td>Actual activity level</td><td>Expected value, calculated with Colby's formula</td>

<td>FORMULA 1) + Trifloxystrobin (ΧΠΙ)</td><td></td><td> 1 + 1</td><td> €8</td><td> 56</td>