Fungicidal combinations of active substances

Fungicidal combinations of active substances

The present invention relates to a novel active combination consisting of the known fluoro-benzothiazole derivatives and also of the known fungicidal active compounds, which are very suitable for controlling phytopathogenic fungi.

It has already been shown that isopropyl 1-({[1-(6-fluoro-1,3-benzothiazol-2-yl)ethyl]amino}carbonyl)-2-methylpropylcarbamate has fungicidal properties. known (cf. EP-A1-775 696). Although the activity of this compound is good, it is sometimes unsatisfactory at low application rates.

It is also already known that a number of triazole derivatives, aniline derivatives, dicarboximides and other heterocycles can be used to control fungi (cf. EP-A 0 040 345, DE-A 22 01 063, DE- A 23 24 010, Pesticide Manual, 9th ed. (1991), pp. 249 and 827, EP-A 0 382 375 and EP-A 0 515 901). Likewise, the activity of these compounds is not always satisfactory at low application rates.

Finally, it is also known that 1-[(6-chloro-3-pyridinyl)-methyl]-N-nitro-2-imidazolidinimine can be used to control animal pests such as insects (cf. Pesticide Manual, 9th ed. (1991), p. 491). However, the fungal properties of this compound have not been described so far.

Also, 1-(3,5-dimethyl-isoxazole-4-sulfonyl)-2-chloro-6,6-difluoro-[1,3]-dioxolo-[4,5f]-benzimidazole It is also already known to have this fungicidal property (cf. WO97-06171).

It is also already known that substituted azodioxacycloalkenes have fungicidal properties (cf. EP-B-712 396).

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

Fluorobenzothiazole derivatives of formula (I) and

(1) triazole derivatives of formula (II) and/or

(2) triazole derivatives of formula (III) and/or

(3) aniline derivatives of formula (IV) and/or

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

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

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

(7) aniline derivatives of formula (VIII) and/or

(8) a compound of formula (IX) and/or

(9) benzothiadiazole derivatives of formula (X) and/or

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

(11) a compound of formula (XII) and/or

(12) a compound of formula (XIII) and/or

(13) a compound of formula (XIV) and/or

(14) cyanoxime derivatives of formula (XV) and/or

(15) pyrimidine derivatives of formula (XVI) and/or

(16) aniline derivatives of formula (XVII) and/or

(17) a morpholine derivative of formula (XVIII) and/or

(18) phthalimide derivatives of formula (XIX) and/or

(19) a phosphorus compound of formula (XX) and/or

(20) hydroxyethyl-triazole derivatives of formula (XXI) and/or

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

(22) oxazolidinediones of formula (XXIII) and/or

(23) benzamide derivatives of formula (XXIV) and/or

(24) guanidine derivatives of formula (XXV) and/or

(25) triazole derivatives of formula (XXVI) and/or

(26) halogeno-benzimidazoles of formula (XXVII) and/or

(27) halogenopyrimidines of formula (XXVIII) and/or

(28) tetrachloro-isophthalo-dinitrile of formula (XXIX) and/or

(29) a compound of formula (XXX) and/or

(30) pyridinamines of formula (XXXI) and/or

(31) thiazolecarboxamides of formula (XXXII) and/or

(32) sulfonamides of formula (XXXIII) and/or

(33) a compound of formula (XXXIV) and/or

(34) a compound of formula (XXXV) and/or

(35) a compound of formula (XXXVI) and/or

(36) diamides of formula (XXXVII) and/or

(37) methoxyacrylate derivatives of formula (XXXVIII) and/or

(38) a quinoline derivative of formula (XXXIX) and/or

(39) phenylamide derivatives of formula (XXXX) and/or

(40) phenylamide derivatives of formula (XXXXI) and/or

(41) dicarboxyime derivatives of formula (XXXXIIa) and/or

(42) phosphonic acids of formula (XXXXIII) and/or

(43) pyrrole derivatives of the formula (XXXXIV) and/or

(44) phenyl carbonate of formula (XXXXV) and/or

(45) a) copper oxychloride (XXXXVIa)

b) a copper compound of copper hydroxide (XXXXVIb) and/or

(46) imidazole derivatives of formula (XXXXVII) and/or

(47) a) formula (XXXXVIIIa) and/or

b) formula (XXXXVIIIb) and/or

c) formula (XXXXVIIIc) and/or

d) formula (XXXXVIIId) and/or

e) formula (XXXXVIIIe) and/or

f) formula (XXXXVIIIf) and/or

g) formula (XXXXVIIIg) and/or

h) triazole derivatives of formula (XXXXVIIIh) and/or

(48) a compound of formula (XXXXIX) and/or

(49) N-methyl-2-(methoxyimino)-2-[2-([1-(3-tri-fluoro-methylphenyl)ethoxy]iminomethyl)phenyl]acetamide of formula (XXXXX) and/or

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

(51) It has been found that a novel active formulation containing a compound of formula (XXXXXII) has very good fungicidal properties:

<img file="KR100613238B1_D0001.tif" />

<img file="KR100613238B1_D0002.tif" />

<img file="KR100613238B1_D0003.tif" />

<img file="KR100613238B1_D0004.tif" />

<img file="KR100613238B1_D0005.tif" />

<img file="KR100613238B1_D0006.tif" />

<img file="KR100613238B1_D0007.tif" />

<img file="KR100613238B1_D0008.tif" />

<img file="KR100613238B1_D0009.tif" />

<img file="KR100613238B1_D0010.tif" />

<img file="KR100613238B1_D0011.tif" />

<img file="KR100613238B1_D0012.tif" />

<img file="KR100613238B1_D0013.tif" />

<img file="KR100613238B1_D0014.tif" />

<img file="KR100613238B1_D0015.tif" />

<img file="KR100613238B1_D0016.tif" />

<img file="KR100613238B1_D0017.tif" />

<img file="KR100613238B1_D0018.tif" />

<img file="KR100613238B1_D0019.tif" />

<img file="KR100613238B1_D0020.tif" />

<img file="KR100613238B1_D0021.tif" />

<img file="KR100613238B1_D0022.tif" />

<img file="KR100613238B1_D0023.tif" />

<img file="KR100613238B1_D0024.tif" />

<img file="KR100613238B1_D0025.tif" />

<img file="KR100613238B1_D0026.tif" />

<img file="KR100613238B1_D0027.tif" />

<img file="KR100613238B1_D0028.tif" />

<img file="KR100613238B1_D0029.tif" />

<img file="KR100613238B1_D0030.tif" />

<img file="KR100613238B1_D0031.tif" />

<img file="KR100613238B1_D0032.tif" />

<img file="KR100613238B1_D0033.tif" />

<img file="KR100613238B1_D0034.tif" />

<img file="KR100613238B1_D0035.tif" />

<img file="KR100613238B1_D0036.tif" />

<img file="KR100613238B1_D0037.tif" />

<img file="KR100613238B1_D0038.tif" />

<img file="KR100613238B1_D0039.tif" />

<img file="KR100613238B1_D0040.tif" />

<img file="KR100613238B1_D0041.tif" />

<img file="KR100613238B1_D0042.tif" />

<img file="KR100613238B1_D0043.tif" />

<img file="KR100613238B1_D0044.tif" />

<img file="KR100613238B1_D0045.tif" />

<img file="KR100613238B1_D0046.tif" />

<img file="KR100613238B1_D0047.tif" />

<img file="KR100613238B1_D0048.tif" />

<img file="KR100613238B1_D0049.tif" />

<img file="KR100613238B1_D0050.tif" />

<img file="KR100613238B1_D0051.tif" />

<img file="KR100613238B1_D0052.tif" />

<img file="KR100613238B1_D0053.tif" />

<img file="KR100613238B1_D0054.tif" />

<img file="KR100613238B1_D0055.tif" />

<img file="KR100613238B1_D0056.tif" />

<img file="KR100613238B1_D0057.tif" />

<img file="KR100613238B1_D0058.tif" />

In formula (II), X represents chlorine or phenyl, and Y is <img file="KR100613238B1_D0059.tif" />or <img file="KR100613238B1_D0060.tif" />represents,

In formula (IV), R<sp>1</sp> represents hydrogen or methyl,

In formula (VII), Me is Zn or Mn, or a mixture of Zn and Mn,

In formula (XVI), R<sp>2</sp> is methyl, <img file="KR100613238B1_D0061.tif" />(mepanipyrim) or cyclopropyl (cyprodinyl),

In the formula (XXV), m represents an integer from 0 to 5, R<sp>3</sp> is hydrogen (17-23%) or the formula <img file="KR100613238B1_D0062.tif" />(77 to 83%) of radicals,

In formula (XXXXIX), R<sp>1</sp> represents unsubstituted or fluorine-, chlorine-, bromine-, methyl- or ethyl-substituted phenyl, 2-naphthyl, 1,2,3,4-tetrahydronaphthyl or indanyl.

Surprisingly, the fungicidal activity of the active combinations according to the invention is much greater than the sum of the activities of the individual active compounds. Thus, it is not a mere sum of activities, but an unexpected true synergistic effect.

From the structural formula of the active compound of formula (I), it can be seen that this compound has two asymmetrically substituted carbon atoms. Thus, the product may exist as a mixture of different isomers or otherwise exist in the form of a single isomer.

Preferred compounds of formula (I) are those in which the amino acid moiety is formed from i-propyloxycarbonyl-L-valine and the fluorobenzothiazoleethylamine moiety is racemic, in particular those having the configuration (R).

Formula (II) is 1-(4-chloro-phenoxy)-3,3-dimethyl-1-(1,2,4-triazol-1-yl)-butan-2-one of formula (IIa) , 1-(4-Chloro-phenoxy)-3,3-dimethyl-1-(1,2,4-triazol-1-yl)-butan-2-one of formula (IIb), formula (IIc) 1-(4-phenyl-phenoxy)-3,3-dimethyl-1-(1,2,4-triazol-1-yl)-butan-2-one of

<img file="KR100613238B1_D0063.tif" />

<img file="KR100613238B1_D0064.tif" />

<img file="KR100613238B1_D0065.tif" />

Formula (IV) includes aniline derivatives of Formula (IVa) and Formula (IVb):

<img file="KR100613238B1_D0066.tif" />

<img file="KR100613238B1_D0067.tif" />

From the structural formula of the active compound of formula (V), it is clear that this compound has three carbon atoms substituted asymmetrically. Thus, the product may exist as a mixture of different isomers or otherwise exist in the form of a single isomer. Particularly preferred is N-(R)-[1-(4-chloro-phenyl)-ethyl]-(1S)-2,2-dichloro-1-ethyl-3t-methyl-1R-cyclopropane of formula (Va) Carboxamide and N-(R)-[1-(4-chloro-phenyl)-ethyl]-(1R)-2,2-dichloro-1-ethyl-3t-methyl-1R-cyclo of formula (Vb) Propanecarboxamide compounds are presented:

<img file="KR100613238B1_D0068.tif" />

<img file="KR100613238B1_D0069.tif" />

Formula (VII) is a compound

(VIIa) Me = Zn (Zineb),

(VIIb) Me = Mn (manneb) and

(VIIc) a mixture of (VIIa) and (VIIb) (mancozeb).

Formula (XVI) is a compound

(XVIa) R<sp>2 </sp>= CH<sb>3 </sb>(pyrimethanil),

(XVIb) R<sp>2 </sp>= <img file="KR100613238B1_D0070.tif" />(cyprodinil) and

(XVIc) R<sp>2 </sp>= <img file="KR100613238B1_D0071.tif" />(mepanipyrim).

Compounds of formula (XVII) may be prepared as methyl N-(2,6-dimethylphenyl)-N-(methoxyacetyl)-DL-alaninate (metalaxyl, XVIIa) or as methyl N-(2,6-dimethylphenyl) )-N-(methoxyacetyl)-D-alaninate (metalaxyl-M, XVIIb).

The hydroxyethyl-triazole derivative of formula (XXI) may exist in the "thiono" form of formula (XXI) or in the tautomeric "mercapto" form of formula (XXIb):

<img file="KR100613238B1_D0072.tif" />

<img file="KR100613238B1_D0073.tif" />

For simplicity, only the "thiono" form is shown in each case.

Guanidine derivatives of formula (XXV) are mixtures of substances with the generic name guazatine.

From the structural formula of the active compound of formula (XXXXIX), it can be seen that this compound may exist as E or Z isomers. Thus, the product may exist as a mixture of different isomers or otherwise exist in the form of a single isomer. Preference is given to compounds of formula (XXXXIX) wherein the compound of formula (XXXXIX) exists as the E isomer. Particular preference is given to the compounds of the formulas (XXXXIXa), (XXXXIXb), (XXXXIXc), (XXXXIXd), (XXXXIXe) and (XXXXIXf) and their isomers:

<img file="KR100613238B1_D0074.tif" />

<img file="KR100613238B1_D0075.tif" />

<img file="KR100613238B1_D0076.tif" />

<img file="KR100613238B1_D0077.tif" />

<img file="KR100613238B1_D0078.tif" />

<img file="KR100613238B1_D0079.tif" />

The following active compounds are particularly preferred mixing partners of the compounds of formula (I):

(3) tolylfluanide (IVb),

(4) propineb (VI),

(6) mancozeb (VIIc),

(7) phenhexamid (VIII),

(8) iprovalicarb (IX),

(11) azoxystrobin (XII),

(12) trifloxistrobin (XIII),

(13) a compound of formula (XIV),

(18) Folpet (XIX);

(20) a compound of formula (XXI),

(26) a compound of formula (XXVII),

(27) a compound of formula (XXVIII),

(28) chlorothalonyl (XXIX),

(30) fluazinam (XXXI) and

(45) a) copper oxychloride (XXXXVIa)

b) A copper compound of copper hydroxide (XXXXVIb).

In addition to halogeno-benzimidazoles of formula (XXVII), the compounds present in the active combinations according to the invention are also known.

In particular, the active compounds are disclosed in the following publications:

(1) a compound of formula (II)

DE-A 22 01 063

DE-A 23 24 010

(2) a compound of formula (III)

EP-A 0 040 345

(3) a compound of formula (IV)

Pesticide Manual, 9<sp>th </sp>Ed. (1991), pp. 249 and 827

(4) compounds of formula (V) and individual derivatives thereof

EP-A 0 341 475

(5) compounds of formula (VI)

Pesticide Manual, 9<sp>th </sp>Ed. (1991), p. 726

(6) compounds of formula (VII)

Pesticide Manual, 9<sp>th </sp>Ed. (1991), pages 529, 531 and 866

(7) a compound of formula (VIII)

EP-A 0 339 418

(8) compounds of formula (IX)

EP-A 0 472 996

(9) a compound of formula (X)

EP-A 0 313 512

(10) a compound of formula (XI)

EP-A 0 281 842

(11) a compound of formula (XII)

EP-A 0 382 375

(12) a compound of formula (XIII)

EP-A-460 575

(13) a compound of formula (XIV)

DE-A 196 02 095

(14) a compound of formula (XV)

Pesticide Manual, 9<sp>th </sp>Ed. (1991), p. 206

(15) a compound of formula (XVI)

EP-A 0 270 111

EP-A 0 310 550

(16) a compound of formula (XVII)

Pesticide Manual, 9<sp>th </sp>Ed. (1991), p. 554

(17) a compound of formula (XVIII)

EP-A 0 219 756

(18) a compound of formula (XIX)

Pesticide Manual, 9<sp>th </sp>Ed. (1991), p. 431

(19) a compound of formula (XX)

Pesticide Manual, 9<sp>th </sp>Ed. (1991), p. 443

(20) a compound of formula (XXI)

WO 96-16048

(21) a compound of formula (XXII)

Pesticide Manual, 9<sp>th </sp>Ed. (1991), p. 491

(22) a compound of formula (XXIII)

EP-A 0 393 911

(23) a compound of formula (XXIV)

EP-A 0 600 626

(24) a substance of formula (XXV)

Pesticide Manual, 9<sp>th </sp>Ed. (1991), p. 461

(25) a compound of formula (XXVI)

Pesticide Manual, 9<sp>th </sp>Ed. (1991), p. 654

(26) a compound of formula (XXVII)

WO 97-06171

(27) a compound of formula (XXVIII)

DE-A1-196 46 407, EP-B-0 712 396

(28) a compound of formula (XXIX)

US 3 290 353

(29) a compound of formula (XXX)

DE-A-156 7169

(30) a compound of formula (XXXI)

EP-A-0 031 257

(31) a compound of formula (XXXII)

EP-A-0 639 547

(32) a compound of formula (XXXIII)

EP-A-0 298 196

(33) a compound of formula (XXXIV)

EP-A-600 629

(34) a compound of formula (XXXV)

DE-A-2 149 923

(35) a compound of formula (XXXVI)

DE-A-2 012 656

(36) a compound of formula (XXXVII)

US 1 972 961

(37) a compound of formula (XXXVIII)

EP-A-326 330

(38) a compound of formula (XXXIX)

EP-A 278 595

(39) a compound of formula (XXXX)

DE-A-3 030 026

(40) a compound of formula (XXXXI)

DE-A-2 903 612

(41) a compound of formula (XXXXII)

US-2 553 770

(42) a compound of formula (XXXXIII)

Known and commercially available

(43) a compound of formula (XXXXIV)

EP-A-206 999

(44) a compound of formula (XXXXV)

EP-A-78 663

(45) a) a compound of formula (XXXXVIa)

Known and commercially available

b) a compound of formula (XXXXVIb)

Known and commercially available

(46) a compound of formula (XXXXVII)

DE-A-2 429 523

(47) a) a compound of formula (XXXXVIIIa)

EP-A-112 284

b) a compound of formula (XXXXVIIIb)

DE-A-3 042 303

c) a compound of formula (XXXXVIIIc)

DE-A-3 406 993

d) a compound of formula (XXXXVIIId)

EP-A-68 813

e) a compound of formula (XXXXVIIIe)

DE-A-2551560

f) a compound of formula (XXXXVIIIf)

EP-A-145 294

g) a compound of formula (XXXXVIIIg)

DE-A-3 721 786

h) a compound of formula (XXXXVIIIh)

EP-A-234 242

(48) a compound of formula (XXXXIX)

WO 96/23763

(49) a compound of formula (XXXXX)

EP-A-596 254

(50) a compound of formula (XXXXXI)

WO 98/23155

(51) a compound of formula (XXXXXII)

EP-A-569 384.

In addition to the active compounds of formula (I), the active combinations according to the invention contain at least one active compound of the compounds of groups (1) to (51). It may also contain further fungicidal active additives.

The synergistic effect is particularly pronounced when the active compounds are present in specific weight ratios in the active combinations according to the invention. However, the weight ratio of active compound in the active combination can be varied within relatively wide limits. In general, it is present in the following proportions with respect to 1 part by weight of the active compound of formula (I):

0.1 to 50 parts by weight of the active compound of group (1), preferably 0.2 to 20 parts by weight,

0.1 to 50 parts by weight of the active compound of group (2), preferably 0.2 to 20 parts by weight,

1 to 150 parts by weight, preferably 1 to 100 parts by weight, of the active compound of group (3),

0.1 to 10 parts by weight of the active compound of group (4), preferably 0.2 to 5 parts by weight,

1 to 150 parts by weight of the active compound of group (5), preferably 5 to 100 parts by weight,

1 to 150 parts by weight of the active compound of group (6), preferably 5 to 100 parts by weight,

0.1 to 50 parts by weight of the active compound of group (7), preferably 1 to 20 parts by weight,

0.1 to 50 parts by weight of the active compound of group (8), preferably 0.2 to 20 parts by weight,

0.02 to 50 parts by weight of the active compound of group (9), preferably 0.1 to 10 parts by weight,

0.1 to 50 parts by weight of the active compound of group (10), preferably 0.2 to 20 parts by weight,

0.1 to 50 parts by weight of the active compound of group (11), preferably 0.2 to 20 parts by weight,

0.1 to 50 parts by weight of the active compound of group (12), preferably 0.2 to 20 parts by weight,

0.1 to 50 parts by weight of the active compound of group (13), preferably 0.2 to 20 parts by weight,

0.1 to 50 parts by weight of the active compound of group (14), preferably 0.2 to 20 parts by weight,

0.2 to 50 parts by weight of the active compound of group (15), preferably 1 to 20 parts by weight,

0.1 to 50 parts by weight of the active compound of group (16), preferably 0.2 to 20 parts by weight,

0.1 to 50 parts by weight of the active compound of group (17), preferably 0.2 to 20 parts by weight,

1 to 150 parts by weight of the active compound of group (18), preferably 5 to 100 parts by weight,

0.1 to 150 parts by weight of the active compound of group (19), preferably 1 to 100 parts by weight,

0.02 to 50 parts by weight of the active compound of group (20), preferably 0.2 to 10 parts by weight,

0.05 to 20 parts by weight of the active compound of group (21), preferably 0.1 to 10 parts by weight,

0.1 to 50 parts by weight of the active compound of group (22), preferably 0.2 to 20 parts by weight,

0.1 to 50 parts by weight of the active compound of group (23), preferably 0.2 to 20 parts by weight,

0.01 to 150 parts by weight of the active compound of group (24), preferably 1 to 100 parts by weight,

0.1 to 50 parts by weight of the active compound of group (25), preferably 0.2 to 20 parts by weight,

0.1 to 50 parts by weight of the active compound of group (26), preferably 0.2 to 20 parts by weight,

0.1 to 50 parts by weight of the active compound of group (27), preferably 0.2 to 20 parts by weight,

1 to 150 parts by weight of the active compound of group (28), preferably 5 to 100 parts by weight,

1 to 150 parts by weight of the active compound of group (29), preferably 5 to 100 parts by weight,

0.1 to 50 parts by weight of the active compound of group (30), preferably 0.2 to 20 parts by weight,

0.1 to 50 parts by weight of the active compound of group (31), preferably 0.2 to 20 parts by weight,

0.1 to 50 parts by weight of the active compound of group (32), preferably 0.2 to 20 parts by weight,

0.1 to 50 parts by weight of the active compound of group (33), preferably 0.2 to 20 parts by weight,

0.1 to 50 parts by weight of the active compound of group (34), preferably 1 to 20 parts by weight,

0.1 to 50 parts by weight of the active compound of group (35), preferably 1 to 10 parts by weight,

1 to 150 parts by weight, preferably 5 to 100 parts by weight, of the active compound of group (36),

0.1 to 50 parts by weight of the active compound of group (37), preferably 0.2 to 20 parts by weight,

0.1 to 50 parts by weight of the active compound of group (38), preferably 0.2 to 20 parts by weight,

0.1 to 50 parts by weight of the active compound of group (39), preferably 0.2 to 20 parts by weight,

0.1 to 50 parts by weight of the active compound of group (40), preferably 0.2 to 20 parts by weight,

1 to 150 parts by weight of the active compound of group (41), preferably 5 to 100 parts by weight,

1 to 150 parts by weight of the active compound of group (42), preferably 5 to 100 parts by weight,

0.1 to 50 parts by weight, preferably 1 to 20 parts by weight, of an active compound of group (43),

0.1 to 50 parts by weight, preferably 1 to 20 parts by weight, of an active compound of group (44),

1 to 150 parts by weight, preferably 5 to 100 parts by weight, of the active compound of group (45a),

1 to 150 parts by weight of the active compound of group (45b), preferably 5 to 100 parts by weight,

0.1 to 50 parts by weight, preferably 0.2 to 20 parts by weight, of an active compound of group (46),

0.1 to 50 parts by weight, preferably 0.2 to 20 parts by weight, of the active compound of group (47a),

0.1 to 50 parts by weight, preferably 0.2 to 20 parts by weight, of the active compound of group (47b),

0.1 to 50 parts by weight of the active compound of group (47c), preferably 0.2 to 20 parts by weight,

0.1 to 50 parts by weight of the active compound of group (47d), preferably 0.2 to 20 parts by weight,

0.1 to 50 parts by weight, preferably 0.2 to 20 parts by weight, of the active compound of group (47e),

0.1 to 50 parts by weight of the active compound of group (47f), preferably 0.2 to 20 parts by weight,

0.1 to 50 parts by weight, preferably 0.2 to 20 parts by weight, of the active compound of group (47 g),

0.1 to 50 parts by weight, preferably 0.2 to 20 parts by weight, of the active compound of group (47h),

0.1 to 50 parts by weight of the active compound of group (48), preferably 0.2 to 20 parts by weight,

0.1 to 50 parts by weight, preferably 0.2 to 20 parts by weight, of an active compound of group (49),

0.1 to 50 parts by weight of the active compound of group (50), preferably 0.2 to 20 parts by weight,

0.1 to 50 parts by weight of the active compound of group (51), preferably 0.2 to 20 parts by weight.

The active combinations according to the invention have very good fungicidal properties, and plant pathogenic fungi, for example Plasmodioporomycetes (<i>Plasmodiophoromycetes</i>), Oomycetes (<i>Oomycetes</i>), chytridiomycetes (<i>Chytridiomycetes</i>), zymycetes (<i>Zygomycetes</i>), Ascomycetes (<i>Ascomycetes</i>), Basidiomycetes (<i>Basidiomycetes</i>), Deuteromycetes (<i>Deuteromycetes</i>) can be used to relieve

The active combination according to the invention is Phytophthora infestans (<i>Phytophthora infestans</i>) and Plasmopara viticola (<i>Plasmopara viticola</i>) is particularly suitable for relieving

Treatment of above-ground parts of plants, propagation stems and seeds, and soil is possible because the plants are tolerant to the active combinations according to the invention at the concentrations necessary for the control of plant diseases. The active combinations according to the invention can be used for foliar applications or as seed dressings.

The active combinations according to the invention can also be used to increase the yield of crops. However, they have reduced toxicity and plants are tolerant of them.

All plants and plant parts can be treated according to the invention. Plants are to be understood as meaning all plants and plant populations, such as desired or undesirable wild plants or crops (including naturally occurring crops). Crops include transgenic plants, include plant varieties that may or cannot be protected by the sovereignty of the plant grower, and are produced by conventional methods of breeding and optimization or by biotechnological methods. and plants obtainable by genetic engineering methods or a combination of these methods. Plant part is understood to mean all parts and organs of a plant that exist above and below the ground, such as shoots, leaves, flowers and roots, examples that may be mentioned include leaves, needles, stems There are stems, trunks, flowers, fruit-bodies, fruits, seeds, roots, tubers and rhizomes. Plant parts also include harvested plants and vegetative and generative propagation material, such as seedings, tubers, rhizomes, cut branches and seeds.

The treatment of a plant or part of a plant according to the invention can be carried out by a conventional treatment method, for example dipping, spraying, evaporating, atomizing, broadcasting, brushing- on), in the case of propagation material, in particular in the case of seeds, by means of a single or multi-layer coating, by acting the active compound on plants and plant parts directly or in their surroundings, habitats or places of storage.

The active formulations according to the present invention can be converted into conventional formulations such as solutions, emulsions, suspensions, powders, foams, pastes, granules, aerosols, microcapsules coated with polymeric substances, coating compositions for seeds and ULV formulations. can

These preparations are prepared in a known manner, for example, optionally by means of surfactants, i.e. emulsifying and/or dispersing and/or foaming agents, by adding the active compound or active formulation to an extender, i.e. a liquid solvent, a liquefied gas under pressure, and/or or by mixing with a solid carrier. If the extender used is water, it is also possible, for example, to use organic solvents as auxiliary solvents. Predominantly suitable liquid solvents are aromatic compounds such as xylene, toluene or alkylnaphthalene, chlorinated aromatic or chlorinated aliphatic hydrocarbons such as chlorobenzene, chloroethylene or methylene chloride, aliphatic hydrocarbons such as cyclohexane or paraffin, such as For example, petroleum fractions, alcohols such as butanol or glycols and their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as dimethylform amides and dimethylsulfoxide, and water. By liquefied gas extender or carrier is meant liquids that are in the gaseous phase at ambient temperature and atmospheric pressure, for example aerosol propellants such as butane, propane, nitrogen and carbon dioxide. Suitable solid carriers are ground natural minerals such as kaolin, clay, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, and ground synthetic minerals such as highly disperse silica, alumina and silicates. Suitable solid carriers for granules are, for example, crushed and classified natural rocks such as calcite, marble, pumice, sepiolite and dolomite, and synthetic granules of inorganic and organic flours, and organic such as sawdust, coconut husks, corncobs and tobacco stalks. are granules of matter. Suitable emulsifiers and/or foam formers are, for example, nonionic and anionic emulsifiers, for example polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkylsulfonates, alkylsulfates , arylsulfonates and protein hydrolysates. Suitable dispersants are, for example, lignin-sulfite waste liquor and methylcellulose.

Adhesives, for example carboxymethylcellulose, and natural and synthetic polymers in powder, granular or latex form, such as gum arabic, polyvinyl alcohol and polyvinyl acetate, and also natural phospholipids such as cephalins and lecithins, and synthetic phospholipids are formulated can be used for Other possible additives include mineral and vegetable oils.

colorants such as inorganic pigments such as iron oxide, titanium oxide and Prussian blue, and organic dyes such as alizarin dyes, azo dyes and metal phthalocyanine dyes and salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc; Micronutrients can be used.

The preparations generally contain from 0.1 to 95% by weight, preferably from 0.5 to 90% by weight of the active compound.

In order to broaden the spectrum of activity and prevent the development of resistance, for example, the active combinations according to the invention can also be applied as such or in the form of preparations thereof, in mixtures with known fungicides, fungicides, acaricides, nematicides or insecticides. have. In many cases, a synergistic effect is obtained, ie the activity of the mixture is greater than the activity of the individual components.

Mixtures with other known actives such as herbicides or with fertilizers and growth regulators are also possible.

The active combinations of the present invention are prepared as such, in the form of preparations thereof or in use forms prepared therefrom, for example ready-to-use solutions, emulsifiable concentrates, emulsions, suspensions, wetting powders, soluble powders and granules. can be used They are used in a customary manner, for example by watering, spraying, misting, sprinkling, application, and as powders for the treatment of dry seeds, solutions for the treatment of dry seeds, water-soluble powders for the treatment of seeds, water-soluble powders for the treatment of slurries, or as husks or hulls. used by formation.

When using the active formulation according to the invention, the application rate can be varied within a relatively wide range depending on the type to be applied. In the case of treatment of plant parts, the application rate of the active combination is generally from 0.1 to 10,000 g, preferably from 10 to 1,000 g per hectare. When treating seeds, the application rates of the active combination are generally from 0.001 to 50 g, preferably from 0.01 to 10 g per kg of seed. When treating the soil, the application rates of the active formulation are generally from 0.1 to 10,000 g, preferably from 1 to 5,000 g per hectare.

The good fungicidal activity of the active combinations according to the invention is evident from the examples below. Although the fungicidal activity of the individual active compounds is negligible, their combination exhibits a superior activity than the simple sum of the individual activities.

A synergistic effect of fungicides is always present if the fungicidal activity of the active combinations is greater than the total activity of the active compounds applied individually.

The expected activity of a combination of two given active compounds can be calculated as follows (see Colby, SR "Calculating Synergistic and Antagonistic Responses of Herbicide Combinations", Weeds) <u>15</u>, (1967), 20-22):

X is active compound A <u>m</u> Represents the effectiveness when used at an application rate of g / ha,

Y represents the active compound B <u>n</u> Indicates the effectiveness when used at an application rate of g/ha,

E is active compounds A and B <u>m</u> and <u>n</u> If it represents the effectiveness when used at an application rate of g/ha,

<img file="KR100613238B1_D0080.tif" />

am.

Validity is calculated in %. 0% is the efficacy corresponding to the control, and an efficacy of 100% means that no infection was observed.

If the actual fungicidal activity is higher than the calculated value, then the activity of the combination is additive, ie in this case a synergistic effect is present. In this case, the practically observed validity is higher than the value for the expected validity (E) calculated from the above-mentioned formula.

The following examples illustrate the invention. However, the examples do not limit the present invention.

<b><u>Example</u></b>

<b><u>Example 1</u></b>

<b>phytophthora (</b><b><i>Phytophthora</i></b><b>) test (tomato) / protective activity</b>

Solvent: acetone 47 parts by weight

Emulsifier: 3 parts by weight of alkylaryl polyglycol ether

1 part by weight of the active compound or active combination is mixed with the above-mentioned amounts of solvent and emulsifier and the concentrate is diluted with water to the desired concentration, or a commercially available preparation of active compound or active combination is diluted with water to the desired concentration to obtain the active compound A suitable formulation was prepared.

To test the protective activity, preparations of the active compounds are sprayed onto young plants at the above-mentioned application rates. After drying the spray coating, the plants were sprayed with Phytophthora infestans (<i>Phytophthora infestans</i>) was inoculated with an aqueous spore suspension. Then, the plant was placed in a culture room at a temperature of about 20 °C and a relative humidity of 100%.

Three days after inoculation, evaluation was performed. 0% is the efficacy corresponding to the control, and an efficacy of 100% means that no infection was observed.

The measured activity for the active combinations according to the invention was greater than the calculated activity. That is, there is a synergistic effect. At a mixing ratio of 1:1 and an application ratio of 0.1 g/ha, the combination of the compound of formula (I) and halogeno-benzimidazole of formula (XXVII) had an effective efficacy of 73%. Expectations calculated using Colby's formula were significantly lower at 65%.

The active compounds, application rates and test results are shown in the table below.

<b><u>Table 1</u></b>

<b>phytophthora (</b><b><i>Phytophthora</i></b><b>) test (tomato) / protective activity</b>

<img file="KR100613238B1_D0081.tif" />

<b><u>Table 2</u></b>

<b>phytophthora (</b><b><i>Phytophthora</i></b><b>) test (tomato) / protective activity</b>

<img file="KR100613238B1_D0082.tif" />

<b><u>Table 3</u></b>

<b>phytophthora (</b><b><i>Phytophthora</i></b><b>) test (tomato) / protective activity</b>

<img file="KR100613238B1_D0083.tif" />

<b><u>Table 4</u></b>

<b>phytophthora (</b><b><i>Phytophthora</i></b><b>) test (tomato) / protective activity</b>

<img file="KR100613238B1_D0084.tif" />

<b><u>Table 5</u></b>

<b>phytophthora (</b><b><i>Phytophthora</i></b><b>) test (tomato) / protective activity</b>

<img file="KR100613238B1_D0085.tif" />

<b><u>Table 6</u></b>

<b>phytophthora (</b><b><i>Phytophthora</i></b><b>) test (tomato) / protective activity</b>

<img file="KR100613238B1_D0086.tif" />

<b><u>Table 7</u></b>

<b>phytophthora (</b><b><i>Phytophthora</i></b><b>) test (tomato) / protective activity</b>

<img file="KR100613238B1_D0087.tif" />

<b><u>Table 8</u></b>

<b>phytophthora (</b><b><i>Phytophthora</i></b><b>) test (tomato) / protective activity</b>

<img file="KR100613238B1_D0088.tif" />

<b><u>Table 9</u></b>

<b>phytophthora (</b><b><i>Phytophthora</i></b><b>) test (tomato) / protective activity</b>

<img file="KR100613238B1_D0089.tif" />

<b><u>Table 10</u></b>

<b>phytophthora (</b><b><i>Phytophthora</i></b><b>) test (tomato) / protective activity</b>

<img file="KR100613238B1_D0090.tif" />

<b><u>Table 11</u></b>

<b>phytophthora (</b><b><i>Phytophthora</i></b><b>) test (tomato) / protective activity</b>

<img file="KR100613238B1_D0091.tif" />

<b><u>Table 12</u></b>

<b>phytophthora (</b><b><i>Phytophthora</i></b><b>) test (tomato) / protective activity</b>

<img file="KR100613238B1_D0092.tif" />

<b><u>Table 13</u></b>

<b>phytophthora (</b><b><i>Phytophthora</i></b><b>) test (tomato) / protective activity</b>

<img file="KR100613238B1_D0093.tif" />

<b><u>Table 14</u></b>

<b>phytophthora (</b><b><i>Phytophthora</i></b><b>) test (tomato) / protective activity</b>

<img file="KR100613238B1_D0094.tif" />

<b><u>Table 15</u></b>

<b>phytophthora (</b><b><i>Phytophthora</i></b><b>) test (tomato) / protective activity</b>

<img file="KR100613238B1_D0095.tif" />

<b><u>Table 16</u></b>

<b>phytophthora (</b><b><i>Phytophthora</i></b><b>) test (tomato) / protective activity</b>

<img file="KR100613238B1_D0096.tif" />

<b><u>Table 17</u></b>

<b>phytophthora (</b><b><i>Phytophthora</i></b><b>) test (tomato) / protective activity</b>

<img file="KR100613238B1_D0097.tif" />

<b><u>Table 18</u></b>

<b>phytophthora (</b><b><i>Phytophthora</i></b><b>) test (tomato) / protective activity</b>

<img file="KR100613238B1_D0098.tif" />

<b><u>Table 19</u></b>

<b>phytophthora (</b><b><i>Phytophthora</i></b><b>) test (tomato) / protective activity</b>

<img file="KR100613238B1_D0099.tif" />

<b><u>Table 20</u></b>

<b>phytophthora (</b><b><i>Phytophthora</i></b><b>) test (tomato) / protective activity</b>

<img file="KR100613238B1_D0100.tif" />

<b><u>Table 21</u></b>

<b>phytophthora (</b><b><i>Phytophthora</i></b><b>) test (tomato) / protective activity</b>

<img file="KR100613238B1_D0101.tif" />