Composition for the control of plant pests

The present invention relates to a composition for combating plant pests containing certain agonists or antagonists of nicotinergenic acetylcholine receptors of insects in active combination with fungicides.

Agonists or antagonists of the nicotinergenic acetylconin receptors of insects are known from the following publications: EP 464830, 428941, 425978, 386565, 383091, 375907, 364844, 315826, 259738, 254859, 235725, 212600, 192060, 1636570, 154, 30435, 15435, 30435, 154 , 302833, 306696, 189972, 455000, 135956, 471372, 302389; DE 3639877, 3712307; JP 03 220176, 02 207083, 63 307857, 63 287764, 03 246283, 04 9371, 03 279359, 03 255072; US 5034524, 4948798, 4918086, 5039 686, 5034404; PCT patent applications WO 91/17659, 91/4965, French patent application 2611114, Brazilian patent application 88 03 621. The present invention refers expressly to the methods, processes, formulas and definitions described in these publications as well as to the individual preparations and compounds described in these materials.

Fungicidal active substances are known, such as azole derivatives, arylbenzyl ethers, benzamides, morpholine compounds and other heterocycles, (paper "Plant protection and pest control", pp. 140 ... 153, Georg Thieme, Stuttgard, 1977, EP-OS O 40 345, DE-05 2324010, DE-05 2201063, EPOS O 112284, EPOS O 304758 and DD-PS 140412). Mixtures of certain nitromethylene derivatives with fungicidal active substances and the use of such mixtures as pest control agents are known and described in U.S. Patent No. 473,1385 and in Japanese Patents JPOS 63-68507, 63/68505, 63/72608, 63 / 72609, 63/72610. The mixtures of certain nitromethylene with open chain and nitroguanidine with fungicides are described in JRO5 30 47106; US-P 5181 587. Mixtures of cyclopropylcarboxamides with certain nitromethylene derivatives or nitroguanidine derivatives are described in JPOS 32 71207. Mixtures of imidacloprid and fungicidal active substances for the protection of materials against termites, but not against plant pests, are also known. Mixtures of imidacloprid and azolylmethylcycloalkanes especially, triticonazole are described in EP-OS 545834. However, it has not been known that nitroguanidine and fungicide derivatives with the exception of cyclopropyl carboxamides and triticonazole influence each other in a favorable manner, so that they can be used as plant pest control agents, being at the same time well supported by plants.

The composition, according to the invention, eliminates the disadvantages of the known compositions, in that it has in its composition a compound of general formula (I):

BN

<img file="RO117226B1_D0001.tif" />

W

XB (O

Bl 117 where6: X represents, = CH- or = N-,

E represents N0₂ or CN,

R represents heteroarylmethyl with up to 6 ring atoms and N, O, S as heteroatoms which are optionally substituted with alkyl radicals having 1 to 4 carbon atoms, alkoxy having 1 to 4 carbon atoms, alkylthio having 1 to 4 carbon atoms 50, haloalkyl having 1 to 4 carbon atoms and 1 to 5 halogen atoms, wherein the halogen atoms are the same or different; hydroxyl; halogen; cyano; nitro; amino; monoalkyl- and dialkylamino, having 1 to 4 carbon atoms in the alkyl group,

A represents hydrogen or alkyl radicals with 1-4 carbon atoms, 55

Z represents C1-6 alkyl radicals, or

A and Z together with the atoms to which they are linked form a saturated or unsaturated heterocycle, having 5- to 7- atoms which may contain 1 or 2 more heteroatoms and / or identical or different heterogroups, in which the heteroatoms are oxygen or nitrogen and the heterogroups are N-alkyl, alkyl or N-alkyl containing 1 to 60 4 carbon atoms in admixture with a fungicide selected from the nitrogen derivatives of general formula (II):

<td>R^of, l 3 RCR I (CH₂)„</td><td> 65</td>

<td>u</td><td> 70</td>

<td>(H)</td><td> 75</td>

<td>in which:</td><td></td>

<td>(IM)</td><td></td>

<td>_z--- -ch-ch₃</td><td> 80</td>

(CIPROCONAZOL) i (4-chlorophenyl) -o- (1-cyclopropylethyl) -1H-1,2,4 triazole-1-ethanol (I116) R '-. R '- -CHCHOHHXCH,) ,, n - 0, R * - H, (TRIADIMENOL) ((1RS, 2RS; 1RS, 2SR) -1 - (4-chlorophenoxy) -3,3dimethyl-1 - (1 H- 1,2,4-triazol-1-90 yl) butane-2-01

RO 117226 Bl and a compound of formula:

<img file="RO117226B1_D0002.tif" />

OCHj (VIII) (AZOXISTROBIN) methyl (E) -2- {2- [6- (2-cyanophenoxy) pyrimidin-4-yloxy] phenyl} -3-methoxyacrylates a compound of the formula:

<img file="RO117226B1_D0003.tif" />

(KRESOXIM-METHYL) Methoxymino- (2-O-tolyloxymethyl-phenyl) -acetic acid methyl ester a compound of the formula:

<img file="RO117226B1_D0004.tif" />

in which:

(XVI-2) R₁₃ = CH₃

TOLILFLUANID a compound of formula:

<img file="RO117226B1_D0005.tif" />

RO 117226 Bl

145 (METALAXYL) N- (2,6-dimethylphenyl] -N- (methoxyacetyl) -DL-alanine methyl ester a compound of the formula:

s θ (CH₃)₂N - {^ -N (CH₃)₂ ss (XXXIV) (THIRAM) Tetramethylthiurom disulfide a compound of the formula:

A

II (CH₃) JCH-OC ~

NH-CH-C-NH-CH

II l

The CH

<img file="RO117226B1_D0006.tif" />

150 (XXXVIII)

VALICARBAMID a compound of formula:

A

<img file="RO117226B1_D0007.tif" />

155

160 (TRIAZOXID) 7 chloro-3-imidazol-1-yl-1,2,4-benzotriazin 1-oxide and compounds of the formula:

<img file="RO117226B1_D0008.tif" />

165 in which:

<img file="RO117226B1_D0009.tif" />

170

175 and (Fenpiclonil)

4- (2,3-dichlorophenyl) pirro-3-carbonitrile

180

RO 117226 Bl

The composition, according to the invention, has the advantage of a synergistic effect with very good fungicidal properties, as it can be used in the control of cereal diseases, in the fight against phytopathogenic fungi, as well as in the control of the animal pests, preferably of the Arthropods, especially of the insects that appear in agriculture, in forests as well as in hygiene.

In the following, a series of data and explanations are presented which allow a better understanding of the invention.

Thus, preferably, the invention relates to compositions used against pests of plants containing as compounds of formula (I), in which, the radicals have the following meanings;

X represents = CH- or = N-,

E represents N0₂ or CN,

R represents heteroarylmethyl, heteroarylethyl with up to 6 ring atoms with N, O, S, preferably N as heteroatom. Mention may be made of substituted thienyl, furyl, thiazolyl, imidazolyl, pyridyl. Preferably, alkyls with 1 to 4, preferably 1 or 2 carbon atoms, for example methyl, ethyl, n- and l-propyl, η-, I- and preferably are mentioned as substituents. t-butyl; alkoxy, preferably 1 to 4, in particular 1 or 2 carbon atoms such as, for example, methoxy, ethoxy, n- or 1-propyloxy and η-, I- or t-butyloxy; alkylthio with preferably 1 to 4 and in particular 1 or 2 carbon atoms such as, for example, methylthio, ethylthio, n- and l-propylthio and η-, I- and t-butylthio; halogenalkyl, preferably 1 to 4, in particular 1 or 2 carbon atoms, preferably 1 to 5 or 1 to 3 halogen atoms, the halogen atoms being the same or different and preferably fluorine , chlorine or bromine, especially fluorine, such as trifluoromethyl; hydroxy; halogen, preferably fluorine, chlorine, bromine and iodine, in particular fluorine, chlorine and bromine; cyano; nitro; amino; monoalkyl- and dialkylamino with preferably 1 to 4, in particular 1 or 2 carbon atoms in each alkyl group, such as methylamino, methyl ethylamino, n- and l-propylamino and meth-n-butyl amino;

A represents hydrogen, C 1-4 alkyl, in particular methyl or ethyl,

Z represents C 1-4 alkyl, in particular ethyl or methyl, -NH (C 1-6)_M-C 1-4 alkyl-C 1-4 alkyl or A and Z together with the atoms to which a saturated or unsaturated heterocyclic ring is attached. The heterocyclic ring may also contain 1 or 2 other heteroatoms and / or identical or different heterogroups. As heteroatoms, oxygen or nitrogen are preferably taken into account and as N-alkyl, alkyl of the N-alkyl group containing 1 to 4, preferably 1 or 2 carbon atoms. The alkyl radicals include methyl, ethyl, n- and l-propyl and η-, I- and t-butyls. The heterocyclic ring contains 5 to 7, preferably 5 or 6 ring members. Examples of heterocyclic rings are pyrrolidine, piperidine, thiazolidine, piperazine, imidazolidine, hexamethyleneimine, hexahydro 1,3,5-triazine, morpholine, which may be optionally substituted with methyl.

Most preferred are compounds of the formula (la) and (lb):

<img file="RO117226B1_D0010.tif" />

(Lb)

Subst —H—,.

\ z^U)^{8 X}&lt;^0H2&gt; n ^ '\ /^(Z) \a)^z

II no₂

RO 117226 Bl where: n is 1 or 2.

The substituents are those mentioned above, in particular, halogen, preferably chlorine, 235

A and Z have the meanings mentioned above, as preferred.

individually, the following compounds are mentioned:

<img file="RO117226B1_D0011.tif" />

240

245

250

255

260

265

As fungicides in the compositions according to the invention, for the control of some pests of plants are mentioned by way of examples:

270

RO 117226 Bl (1) Azole derivatives of the formula:

R²

J 3 R¹-CR³

I (ch₂)_a

<img file="RO117226B1_D0012.tif" />

(Π) (II-l)

<img file="RO117226B1_D0013.tif" />

(Tebuconazole)

BUT

<img file="RO117226B1_D0014.tif" />

R³, R³ = -OCH₂CH (CH₃) 0-, (DEFENCONAZOLE)

<img file="RO117226B1_D0015.tif" />

(CYPROCONAZOLE) (II

RO 117226 Bl i,

<img file="RO117226B1_D0016.tif" />

(Flutriafol)

320

<img file="RO117226B1_D0017.tif" />

(Π-7)

R¹ =

<img file="RO117226B1_D0018.tif" />

(Myclobutanil)

325

330

335

<img file="RO117226B1_D0019.tif" />

R² = - (CH₂)₂CH₃R³-H, n = l, «

(Penconazole)

340

RO 117226 Bl (Π-9) R^it

<img file="RO117226B1_D0020.tif" />

<img file="RO117226B1_D0021.tif" />

,. -OCHCKCH, -

R'.R? - I ' ²

OCH₂CF₃ n = 1, (FURCONAZOLE) (Π-10) R^it

<img file="RO117226B1_D0022.tif" />

(ETACONAZOLE) (II-ll) R¹

<img file="RO117226B1_D0023.tif" />

<img file="RO117226B1_D0024.tif" />

»2 t.3 -och₂chch_-, R², R³ = ²1 n = 1,

Br (BROMUCONAZOLE) (11-12) R¹

<img file="RO117226B1_D0025.tif" />

(11-13) R¹

<img file="RO117226B1_D0026.tif" />

<img file="RO117226B1_D0027.tif" />

<img file="RO117226B1_D0028.tif" />

<img file="RO117226B1_D0029.tif" />

(11-14) R¹

<img file="RO117226B1_D0030.tif" />

(FENBUCONAZOLE)

RO 117226 Bl

<img file="RO117226B1_D0031.tif" />

385 (TETRACONAZOLE) (Π-16) R¹ =, R² - -CH (OH) 'C (CH₃)₃, n = 0, R³ - H,

390 (TRIADIMENOL) (Π-17) R^it - d - ^^ O, R² - -CO-C (CH₃) 3, n = 0, R³ = H,

395 (Triadimefon)

400 (Π-18) R¹

R³

<img file="RO117226B1_D0032.tif" />

-CHiOHj-CCCH ^, n - 0,

405 (Bitertanol)

<img file="RO117226B1_D0033.tif" />

(Diclobutrazole)

-CH (OH) -C (CH₃)₃, n - 0, R³ - H,

410

<img file="RO117226B1_D0034.tif" />

(DINICONAZOL). OH '= I, n = 0,

-CH-tButyl

415

Azole derivatives of the formula:

420

RO 117226 Bl

<img file="RO117226B1_D0035.tif" />

(FLUSELAZOLE) (in)

Azole derivative of formula

<img file="RO117226B1_D0036.tif" />

<img file="RO117226B1_D0037.tif" />

(PROCHLORAZ) (IV) (V) azole derivative of formula

<img file="RO117226B1_D0038.tif" />

<img file="RO117226B1_D0039.tif" />

(FLUQUINC ONAZOLE)

Heterocycles of formula

RO 117226 Bl

460

R¹ )—\

N N-CH.-CH-CH.-R "

R⁸ (VH) (vn-1)

X- 0.R¹ = CH3, R⁹ - H, R¹⁰ «CJ0H₂₁

465 (TRIDEMORPH) (VH-2)

X = 0, R⁸ - CHj, R⁹ - H, R '° = CjHj,

470 (ALDIMORPH) (ΥΠ-3)

X = 0. R⁸ = CH3, R⁹ = CH3, R¹⁰ (FENPROPIMORPH) (ΥΠ-4)

X = CH₂, R⁸ «H, R⁹ - CH₃, R^w =

<img file="RO117226B1_D0040.tif" />

475

480 (Fenpropidine)

485

Compound of formula

<img file="RO117226B1_D0041.tif" />

CN

<img file="RO117226B1_D0042.tif" />

(VHI)

OCH

490

Compound of formula

495

RO 117226 Bl

<img file="RO117226B1_D0043.tif" />

OCHj (DC)

Compound of formula

<img file="RO117226B1_D0044.tif" />

BUT

<img file="RO117226B1_D0045.tif" />

OCH

QO) (PYRIFENOX)

Compound of formula

<img file="RO117226B1_D0046.tif" />

Compound of formula (XII)

RO 117226 Bl

540

<img file="RO117226B1_D0047.tif" />

(TRIFLUMIZOLE) (MU)

545

Compounds of formula

550

<img file="RO117226B1_D0048.tif" />

ci (MV)

555 ραν-ΐ) ραν-2) (XIV-3)

<img file="RO117226B1_D0049.tif" />

a

R¹¹ - -N λ O ch₃CH = CH₂ (Vinclozolin)

<img file="RO117226B1_D0050.tif" />

(Procymidone)

<img file="RO117226B1_D0051.tif" />

(Iprodione)

560

565

570

575

580

RO 117226 Bl (XV)

Compounds of formula

<img file="RO117226B1_D0052.tif" />

(XV-1) R¹² = CH₃ (PYRIMETHANIL) (XV-2) R¹² = CkC-CHj (MEPANIPYRJM)

Compounds of Formula (XVI-1)

<img file="RO117226B1_D0053.tif" />

(DICHLORFLUANID) (XVI) (XVI-2) R¹³ - CH₃ (Tolylfluanid)

Compound of formula

<img file="RO117226B1_D0054.tif" />

(DITHIANON) (XVII)

Compound of formula

RO 117226 Bl

HjC-iCH ^ -NH ^ NH_of Ch ^ COjH C II NH (xvm)

630 (Dodine)

635

Compound of formula

<img file="RO117226B1_D0055.tif" />

(CHLOROTHALONIL)

<img file="RO117226B1_D0056.tif" />

(XIX)

640

645

Compound of formula

<img file="RO117226B1_D0057.tif" />

(Dimethomorph)

650

655

660

Compound of formula

<img file="RO117226B1_D0058.tif" />

(METALAXYL) (XXI)

665

670

RO 117226 Bl

Compound of formula

H_sC₂-NH-CO-NH-CO-C = N-EYES (ΧΧΠ)

CN (CYMOXANILE)

Compound of formula

<img file="RO117226B1_D0059.tif" />

(FLUAZINAM) (xxm)

Compound of formula | ÎJXX&gt; o (xxrv)

Compounds of formula

CljC-SR¹⁴ (XXV) (XXV-1) R¹⁴ =

<img file="RO117226B1_D0060.tif" />

(CAFTAN) (XXV-2) R¹⁴ =

<img file="RO117226B1_D0061.tif" />

RO 117226 Bl (FOLPET)

720

Compound of formula

<img file="RO117226B1_D0062.tif" />

(ANILAZIN) (26)

725

730

Compound of formula

<img file="RO117226B1_D0063.tif" />

(Oxadixyl)

<img file="RO117226B1_D0064.tif" />

(XXVII)

735

740

Compound of formula

745

<img file="RO117226B1_D0065.tif" />

(AL FOSETYL) (XXVHI)

750

RO 117226 Bl

<img file="RO117226B1_D0066.tif" />

Compound or formula

O-CO-CH = CH-CH (XXIX)

Compound of formula

<img file="RO117226B1_D0067.tif" />

(XXX)

CF

Compound of formula

<img file="RO117226B1_D0068.tif" />

(XXXI)

RO 117226 Bl

790

<img file="RO117226B1_D0069.tif" />

Compound of formula

795 (XXXII)

800

Compounds of formula

805

N— # f S

I

M

<img file="RO117226B1_D0070.tif" />

(XXXIII)

810 (XXXX-1) M = Zn (ZINEB)

815 (ΧΧΧΙΠ-2) M = Mn (MANEB) (ΧΧΧΙΠ-3) M = Mn / Zn (Mancozeb)

Compound of formula

SS

SS (THIRAM) (xxxiv)

820

Compound of formula

830

RO 117226 Bl (XXXV)

<img file="RO117226B1_D0071.tif" />

(TYMIBENCONAZOLE)

Compound of Formula [(S-CS-NH-CHj-CHj-NH-CS-S-) 'ZiKNH,),)] (-S-CS-NH-CHj-CHj-NH-CS-S-] (XXXVI ) (METIRAM)

Compound of formula

<img file="RO117226B1_D0072.tif" />

(XXXVII)

Compound of the formula a CH (CH₃), l // \ (CH₃) jCH-OC-NH-CH-C-nh-ch-c / -CH₃ the ch₃ (38) Compounds of formula:

(XXXVIII)

<img file="RO117226B1_D0073.tif" />

in which:

R¹⁵ and R^1B independently of each other represents hydrogen, halogen, methyl or phenyl,

R¹⁷ represents hydrogen or methyl, (39) 8-tert-butyl-2- (N-ethyl-Nn-propylamino) -methyl-1,4-dioxaspiro / 4,5 / -decane of the formula:

RO 117226 Bl (40) Compounds of formula:

<img file="RO117226B1_D0074.tif" />

880 / A ^xAh_of-N ^

CH₂0H₂0H₃ (XL)

885

<img file="RO117226B1_D0075.tif" />

890

Compound of formula

A

<img file="RO117226B1_D0076.tif" />

895

Compound of formula

900

<img file="RO117226B1_D0077.tif" />

905

<img file="RO117226B1_D0078.tif" />

Fludioxooil

Fenpidonil

910

915

Compound of formula

920

<img file="RO117226B1_D0079.tif" />

<img file="RO117226B1_D0080.tif" />

RO 117226 Bl

Benzimidazole of the formula

<img file="RO117226B1_D0081.tif" />

R⁹ = CONHtBu; R⁶ = -NHCOOMe

benomyl

R '= H; R^e = -C

<img file="RO117226B1_D0082.tif" />

Thiabendazo!

R⁹ - H; R⁶ »-NHCOOMe

carbendazin

Compound of the formula aNH-CS-NHCOOMe

NH-CS--NHCOOMe

Compound of formula

NH I HN - (CH)_eNH-C-NH

Compound of formula

<img file="RO117226B1_D0083.tif" />

The active substances of formula (I) are known, for example, from the EPOS patent 192060. The fungicidal active substances are also known. These are described in the following publications:

(1) Compounds of formula (II)

DE-OS 2201063

DE-OS 2324010

DE-OS 2737489

DE-OS-3018866

RO 117226 Bl

DE-OS-2551560

EP 47594

DE 2735872 (2) Compounds of formula (III)

EP 68813

US 4496551 (3) Compounds of formula (IV)

DE-OS- 2429523

DE-OS 2856974

US 4108411 (6) Compounds of formula (VII)

DL 140041 (7) Compounds of formula (VIII)

EP 382375 (8) Compound of formula (IX)

EP 515901 (9) Compound of formula (X)

EP 314422 (10) Compound of formula (XI)

EP 49854 (11) Compound of formula (XII)

DE-OS 1770288

US 3869456 (13) Compounds of formula (XIV)

FROM 2207576

US 3903090

US 3755350

US 3823240 (14) Compounds of formula (XV)

EP 270111 (19) Compound of formula (XX)

EP 219756 (34) Compound of formula (XXXV)

US 4512989 (38) Compounds of Formula (XXXIX)

EP 398692

Compounds in groups (15), (16), (17), (18), (23), (34), (25), (28), (31), (32), (33) and (38) up to (47) are described as examples in the work "Plant protection and pest control", author KH Buchel, pp. 121-153, Georg Thieme, Stuttgart, 1977. The compound in group (39) is known from EP-OS 281842. The compositions according to the invention contain, in addition to the active substance of formula (I), at least one fungicidal active substance selected from the compounds of groups (1) to (47). They may additionally contain other active substances, common auxiliaries and additives, as well as dilution agents. When the active substances in the compositions according to the invention are in certain weight ratios, a clear synergistic effect occurs.

970

975

980

985

990

995

1000

1005

1010

RO 117226 Bl

The weight ratios of the active substances can be varied over a relatively wide range, generally used for 1 part by weight of the active substance of formula [I] 0.1 to 10 parts by weight, preferably 0.3 to to 3 parts by weight of at least one fungicidal active substance selected from groups (1) to (48).

The compositions according to the invention have very good fungicidal properties. They can be used, in particular, to combat phytopathogenic fungi such as, for example, Plasmodiophoromycetes, Omycetes, Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes, Deuteromycetes and others. They also lend themselves well to combating cereal diseases such as Erysiphe, Cochliobolus, Septoria, Pyrenophora and Leptosphaeria and various fungi in vegetables, vines and fruits, for example, against Venturia or Podosphaera on apples, Uncinula to vines or Sphaeroteca to cucumbers and to the control of the animal pests, preferably of the Arthropods, especially of the insects that appear in agriculture, in forests to the protection of the provisions and materials, as well as in the hygiene sector. They are effective against the types with normal or resistant sensitivities, as well as at all the individual stages of development. Among the pests mentioned above are: On the order of the Isopods, Oniscus asellus, Armadillium vulgare, Porcelio scaber.

From the order of the Diplopods, Blaniulus guttulatus.

From the order of Chilopods, Geophilus carpophagus, Scutigera spec.

From the order of the Symphylos, Scutigerella immaculata.

From the order of the Thysanures, Lepisma saccharina. From the order of the Collemboles, Onychiurus armatus.

From the order of the Orthoptera, Blatta orientalis, Periplaneta americana, Leucophaea maderae, Blattella germanica, Acheta domesticus, Gryllotalpa spp., Locusta migratoria migratoriorides, Melanoplus differentialis, Schistocerca gregaria.

From the order of the Dermapter, the Headache Formula.

On the order of the Isoptera, Reticulitermes spp.

From the order of the Anopluras, Pediculus humanus corporis, Haematopinus spp., Linognatus spp.

From the order of Mallophageas, Trichodectes spp., Damalinea spp.

From the order of the Thysanopterans, Hercinothrips femoralis, Thrips tabaci.

From the order of Heteroptera, Eurygaster spp., Dysdercus intermedius, Piesma quadrata, Cimex lectularius, Rhodnius prolixus, Triatoma spp.

From the order of the Homoptera, Aleurodes brassicae, Bemisia tabaci, Trialeurodes vaporariorum, Aphis gossypii, Brevicoryne brassicae, Cryptomyzus ribis, Doralis fabae, Doralis pomi, Eriosoma lanigerum, Hyalopterus arundinis, Macrosiphum avenae, Myzop sphum, Phor spor. Pemphigus spp., Empoasca spp., Euscelis bilobatus, Nephotettix cincticeps, Lecanium corni, Saissetia oleae, Laodelphax striatellus, Nilaparvata lugens, Aonidiella aurantii, Aspidiotus hederae, Pseudococcus spp., Psylla spp.

From the order of Lepidopteras, Pectinophora gossypiella, Bupalus piniarius, Cheimatobia brumata, Lithocolletis blancardella, Hyponomeuta padella, Plutella maculipennis, Malacosoma neustria, Euproctis chrysorrhoea, Lymantria spp., Bucculatrix spuristis, Phrocella sp. Earias insulana, Heliothis spp., Laphygama exigua, Maamestra brassicae, Panolis flammea, Prodenia titura, Spodostera spp., Trichoplusia ni, Carpocapsa pomonella, Pieris spp., Chilo spp., Pyrausta nubilalis, Ephestia kuehniella, Galleria mellonella, Tineola bisselliella, inea line pelionella, Hofmannophila pseudospretella, Cacoecia podana, Capua reticulana,

RO 117226 Bl

1065

Choristoneura fumiferena, Clysia ambiguella, Homona magnanium, Tortrix viridana. From the order of Coleoptera, Anobium puncttatum, Rhizopertha dominica, Bruchidius obtectus, Acanthoscelides obtectus, Hylotrupes bajulus, Agelastica alni, Leptinotarsa ​​decemlineata, Phaedon cochlearia, Diabrotica spp., Psylliodes chrysocepus, Epilachna, Epilachna, Epilachna spp., Otiorrhynchus sulcatus, Cosmopolites sordidus, Ceuthorrhynchus axis milis, Hxpera postica, Dermestes spp., Trogoderma spp., Anthrenus spp., Attagenus spp., Lyctus spp., Meligethes aeneus, Ptinus spp., Niptus hololeucus, Gibbium psylloides, Tribolium spp., Tenebrio molitor, Agriotes spp., Conoderus spp., Melolontha melolontha, Amphimallon solstitialis, Costelytra zealandica.

From the order of Hymenoptera, Diprion spp., Hoplocampa spp., Lasius spp., Monomorium pharaonis, Vespa spp.

From the order of Dipteres, Aedes spp., Anopheles spp., Culex spp., Drosophila melanogaster, Musca spp., Fannia spp., Calliophora erythrocephala, Lucillia spp., Chrysomyia spp., Cuterbera spp., Gastrophilus spp., Hyppobosca spp. Stomoxys spp., Oestrus spp., Hypoderma spp., Tabanus spp., Tannia spp., Bibio hortulanus, Oscinella frit, Phorbia spp., Pegomyia hyoscyami, Ceratitis capitata, Dacus oleae, Tipula paludosa.

The combinations of active substances in the concentrations necessary for the control of plant diseases allow the treatment of the parts of the plant above the soil, of the plants, of the seeds and of the soil. The composition, according to the invention, can be conditioned in the form of solutions, emulsions, suspensions, powders, foams, pastes, granules, aerosols in the form of polymer capsules, etc. These conditioners are obtained in a known manner, for example, by mixing the active substances with diluents, thus with liquid solvents, with pressurized liquefied gases and / or solid support substances, possibly with the use of active surface agents, so agents of emulsifiers and / or dispersing agents and / or foaming agents. In the case of using water as a diluting agent, for example, organic solvents may also be used as auxiliary solvents. Aromatic hydrocarbons, such as, xylene, toluene or alkyl naphthalene, chlorinated aromatic hydrocarbons or chlorinated aliphatic hydrocarbons such as chlorobenzene, chlorethylene or methylene chloride, aliphatic hydrocarbons such as paraffin, cyclohexane, can be used as liquid solvents. for example, fractions of petroleum, alcohols, such as, for example, butanol or glycol, as well as their ethers and esters, ketones such as acetone methylethylketone, methylisobutylketone or cyclohexanone, strongly polar solvents such as dimethylformamide and dimethylsulfoxide as well as water. Diluting agents or carrier substances in the form of liquefied gases are those liquids that are gaseous at normal temperature and pressure, for example, aerosol propelling gases, halogenated hydrocarbons, butane, propane, nitrogen and carbon dioxide. The solid carrier substances are chosen from ground rocks, kaolin, aluminum oxides, talc, chalk, quartz, atapulgite, montmorilonite or diatomaceous earth, high dispersed silicic acid, aluminum oxide and silicate. As solid carriers for granulation, crushed and fractionated natural rocks are used, such as calcite, marble, pumice, sepiolite, dolomite, synthetic granules of inorganic and organic flour, as well as granules of organic material, such as sawdust, walnut shells. coconut, corn chips and corn stalks. Non-ionic and anionic emulsifiers such as, for example, polyoxyethylene-fatty acid ester, polyoxyethylene-fatty alcohol ester, such as alkyl arylpolyglycol-ether, alkylsulfonates, alkylsulphates, alkylsulfonates, such as emulsifying agents and / or foaming agents are used. and hydrolyzed albumin. Residual leaches can be used as dispersing agents

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RO 117226 Ligno-sulfite and methyl cellulose. Adhesive agents such as, for example, carboxymethylcellulose, natural polymers and synthetic powders, grains or latex, such as arabic gum, polyvinyl alcohol, polyvinyl acetate, natural phospholipids, and cefolipids, are used to obtain compositions. synthetic lecithins and phospholipids. Other additives are mineral and vegetable oils. Dyes, inorganic pigments, such as, for example, iron oxide, titanium oxide, ferrocyanide blue, and organic dyes such as alizarin dyes, azo dyes and phthalocyanine and small amounts of substances may also be used. food, iron, manganese, boron, copper, cobalt, molybdenum and zinc salts. The compositions according to the invention generally contain between 0.1 and 95% by weight of the active substance, preferably 0.5 ... 90%. These compositions can be used in conjunction with other known active substances such as fungicides, insecticides, acaricides and herbicides, as well as in mixtures with fertilizers or plant growth regulators. The combinations of active substances can be used as such in the form of compositions conditioned as solutions, emulsifiable concentrates, emulsions, suspensions, spray powders, soluble and granulated powders. They are usually applied, for example, by pouring, stopping, spraying, spreading, dry, wet or very wet, slime or inlay. In the treatment of parts of plants, the concentrations of the active substance may vary in a wider range, generally between 1 and 0.0001% by weight, preferably 0.5 ..... 0.001%. In the treatment of seeds, in general, amounts of active substance, between 0.001 and 50 g / kg of seed are used, preferably 0.01 to 10 g / kg of seed. When treating the soil, concentrations of active substance ranging from 0.0001 to 0.1% by weight are required, preferably 0.0001 to 0.02% by weight at the operating site.

Further examples of embodiments of the invention are given below.

Example 1. In this example the active substances are used in powder form. They are prepared by diluting the respective active substance with rock flour to obtain a fine powder mixture that allows a uniform distribution on the seed surface. The composition was tested for Drechslera graminea, (syn. Helminthosporium gramineum], in which barley seeds were treated. In order to obtain the powder composition, the infected seeds are shaken for 3 minutes with the respective powder in a closed glass bottle. The seeds are included in standard soil, moist, in Petri dishes in the refrigerator, for 10 days, at a temperature of 4 ° C. Exposure to this temperature starts the barley sprouting and sprouting the sprouts of barley. Then, the prewarmed barley resembles 2 x 50 grains, at a depth of 3 cm in a standard soil and grown in a greenhouse, at a temperature of 18 ° C in seed boxes that are exposed daily 15 h at the light. Approximately 3 weeks after sowing, plant recovery takes place. Imidacloprid mixtures with Tebuconazole, Captan, Euparen M, Bitertanol, Triaz oxides, Thiram, Fludioxonil show a clear increase in the effect compared to treatment with individual active substances.

Example 2. The active substances are used in the form of dry powders which are prepared by diluting the respective active substance with rock flour to obtain a fine powder mixture that allows a uniform distribution on the seed surface. For this, the infected seeds are shaken for 3 minutes with the powder in a closed glass bottle. The composition is tested for Fusarium nivale, treating wheat seeds. The wheat resembles 2 x 100 grains, 1 cm deep in a standard soil and is grown in a greenhouse, at a temperature of about 10 ° C and a relative air humidity of about 95% in special boxes for sowing in which they are exposed to daylight, for 15 hours. After approx

RO 117226 Weeks of planting takes place the recovery of the plants according to the symptoms of the white mold. The mixtures of Imidacloprid with Europaren, Guazatine, Triadimenol, Difenconazole, Feniclonil show a considerable increase in efficiency, compared to the treatment with individual active substances.

Example 3. As a solvent, 7 parts by weight of dimethylformamide and 1 part by weight of alkylarylpolyglycolether are used as emulsifier. To obtain the appropriate active substance preparation, mix 1 part by weight of the active substance with an amount indicated by the emulsifier and solvent and dilute the concentrate with water to the desired concentration. Tested for Phaedon larvae. The cabbage leaves (Brassica oleracea) are treated by immersion in the active substance preparation with the desired concentration and covered with beetle larvae of sea radish leaves, [Phaedon cochleariae as long as the leaves are moist). After 7 days the effectiveness is determined by the degree of killing expressed as a percentage. The mixtures of Imidacloprid with Anilazine, Benomyl, Bitertanol, Captan, Diclofluanid, Mancozeb, Maneb, Metalaxyl, Prochloraz, Procymidone, Sulfur, Tolylfluanid, Triadimefon, Triadimenol show in this case a considerable increase in the efficacy of the individual drug efficacy.

Example 4. As a solvent, 7 parts by weight of dimethylformamide and 1 part by weight of alkylarylpoliglycololeter are used as emulsifier. To obtain the preparation of the appropriate active substance, mix 1 part by weight of active substance with the indicated amount of solvent and emulsifier and add water to the desired concentration. The cabbage leaves are treated (Brasica oleracea), which are strongly affixed with the peach leaf lice, (Myzus persicae], by immersion in the preparation of active substance with the desired concentration. After 6 days, the percentage killing is determined. Imidacloprid mixtures with Bitertanol, Fenpropimorph, Prochloraz, Tebuconazole show a marked increase in efficacy compared to treatment with individual active substances.

Example 5. As a solvent, 4.7 parts by weight of acetone are used and as emulsifier 0.3 parts by weight of alkylarylpolyglycolether. To obtain a suitable preparation of active substance, mix 1 part by weight active substance with the indicated amounts of solvent and emulsifier and dilute with water to the desired concentration. The product is tested for Botrytis on beans. In order to examine the effectiveness of the protection, the young plants are sprayed with the active substance preparation until dripping moisture. After drying the sprayed layer, put on each leaf 2 pieces of agar on which Botrytis grew the ash. The inoculated plants are placed in a moist, dark room at 20 ° C. 3 days after inoculation, the size of the infested spots on the leaves is determined. The mixtures of Imidacloprid with Procymidone, Tolyfluanid, Tebuconazole show in this case a considerable increase in efficiency compared to treatment with individual compounds.

Example 6. 4.7 parts by weight of acetone are used as solvent and 0.3 parts by weight of alkyl-aryl-polyglycolether as emulsifier. To obtain the appropriate preparation, mix 1 part by weight active substance with the indicated amounts of solvent and emulsifier and dilute the concentrate with water to the desired concentration. In order to examine the effectiveness of apple protection with Podosphaera, young plants are stopped with the preparation thus obtained until dripping moisture. After drying the sprayed layer the plants are inoculated by dust with conidia of the pest that produces apple mold, Podosphaera leucotricha. The plants are then placed in a greenhouse at 23 ° C and a relative humidity of about 70%. Efficiency is determined 10 days after inoculation.

The mixtures of Imidacloprid with Fenpropidin, Triadimenol in this case show a considerable increase in the efficiency compared to the treatment with individual compounds.

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RO 117226 Bl

The synergistic effect for a composition consisting of two compounds can be calculated according to the following formula (according to Coliby, SR, "Calculation of synergistic and antagonistic responses of herbicidal combinations", Weeds 15, pp. 20-22, 1967):

If:

X represents the effectiveness expressed in% of untreated plants, using a dose of mg / ha active compound "A", and

Y represents the efficiency expressed in% of untreated plants, using a dose of ng / ha active compound “B and

E represents the efficiency expressed in% of untreated plants, using a mixture dose of mg / ha active compound "A" and ng / ha active compound Έ ", then:

E = X + Y - (X x Y) / 1OO

If the efficiency actually obtained for the mixture is greater than that estimated by calculation, then the mixture is synergistic.

The following is a number of biological tests that demonstrate the practical applicability and synergistic properties of the composition according to the invention. Table 1 shows the compounds used in the following tests.

Table 1

Molecular structure and names of the compounds tested

<td>Compound</td><td>Structural formula</td>

<td>Compound 1 according to the invention</td><td>^α-Ο ~ \^N_yr? OjN H</td>

<td>Compound 2 according to the invention</td><td>HN ^ /ⁿ^ ch₃^NNO_z</td>

<td>Compound 3 according to the invention</td><td>N— 'N — v NC</td>

<td>Compound 4 according to the invention</td><td> --- ^NNO₂</td>

<td>cyproconazole</td><td>Toh</td>

<td>Valicarbamida The compound of formula (XXXVIII)</td><td>a CH IJ</td>

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1260

Table 1 [continued]

<td>Compound</td><td>Structural formula</td>

<td>triadimenol</td><td>Ηθ | ° ΎΠΐ</td>

<td>fludioxonil</td><td>rțg- · CN The «</td>

<td>fenpiclonil</td><td>CN A</td>

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

<td>tolylfluanid</td><td>Xi H, C</td>

<td>azoxystrobin</td><td>QXU? CN H.CO ^ J ^ OCH,</td>

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1275

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1285

Test A.

Phytophthora test (red) / protective Solvent: 47 parts by weight acetone Emulsifier: 3 parts by weight alkylaryl polyglycol ether

To make a suitable preparation of the active compound, 1 part by weight of the active compound is mixed with the mentioned amounts of solvent and emulsifier and the concentrate is diluted with water to the desired concentration. To test the protective action, the young plants are sprayed with the preparation containing the active compound at the mentioned application doses. After spraying the coating layer dries, and the plants are inoculated with a suspension of spores infested with Phytophtora in aqueous solution. The plants are then placed in an incubator at about 20 ° C and a relative atmospheric humidity of 100%. The test is evaluated 3 days after inoculation. 0% represents an efficacy that corresponds to that of the control, while an efficiency of 100% indicates the absence of any disease. In this test the following compositions have synergistic effect compared to the individual compounds.

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Table A

Pests fungi for plants Phytophthora test (tomatoes) / protection

<td>A compound / composition</td><td>Quantity applied [g / ha]</td><td>Actual / Calculated effectiveness</td>

<td>Compound 1</td><td>5oo</td><td> 55</td>

<td>Compound 2</td><td> 500</td><td> 51</td>

<td>Compound 3</td><td> 500</td><td> 46</td>

<td>Compound 4</td><td> 500</td><td> 41</td>

<td>propiconazole</td><td> 500</td><td> 5</td>

<td>Compound 1 + Propiconazole</td><td> 500 + 500</td><td> 68/57</td>

<td>Compound 2 + Propiconazole</td><td> 500 + 500</td><td> 69/53</td>

<td>Compound 3 + Propiconazole</td><td> 500 + 500</td><td> 68/49</td>

<td>Compound 4 + Propiconazole</td><td> 500 + 500</td><td> 58/44</td>

<td>Compound 1</td><td> 50</td><td> 4</td>

<td></td><td> 10</td><td> 0</td>

<td>Compound 2</td><td> 50</td><td> 19</td>

<td>Compound 4</td><td> 10</td><td> 0</td>

<td>tolylfluanid</td><td> 50</td><td> 70</td>

<td>Valicarbamid</td><td> 10</td><td> 61</td>

<td>metalaxyl</td><td> 50</td><td> 42</td>

<td>Compound 1 + Tolylfluanide</td><td> 50 + 50</td><td> 87/71</td>

<td>Compound 1 + Valicarbamide</td><td> 10+ 10</td><td> 78/61</td>

<td>Compound 1 + Metalaxyl</td><td> 50 + 50</td><td> 65/44</td>

<td>Compound 2 + matalaxil</td><td> 50 + 50</td><td> 68/53</td>

<td>Compound 4 + Valicarbamide</td><td> 10 + 10</td><td> 89/61</td>

<td>Compound 1</td><td> 10</td><td> 0</td>

<td>Compound 2</td><td> 500</td><td> 55</td>

<td>Compound 3</td><td> 50</td><td> 11</td>

<td></td><td> 10</td><td> 0</td>

<td>Compound 4</td><td> 50</td><td> 33</td>

<td>triadimenol</td><td> 500</td><td> 0</td>

<td>tolylfluanid</td><td> 50</td><td> 34</td>

<td>Valicarbamid</td><td> 10</td><td> 88</td>

<td>azoxystrobin</td><td> 10</td><td> 74</td>

<td>Compound 2 + Triadimenol</td><td> 500 + 500</td><td> 63/55</td>

<td>Compound 3 + Tolylfluanide</td><td> 50 + 50</td><td> 51/41</td>

<td>Compound 4 + Tolylfluanide</td><td> 50 + 50</td><td> 70/56</td>

<td>Compound 3 + Valicarbamide</td><td> 10 + 10</td><td> 96/88</td>

<td>Compound 1 + Azoxistrobin</td><td> 10+ 10</td><td> 84/74</td>

<td>Compound 3 + Azoxistrobin</td><td> 10 + 10</td><td> 86/74</td>

RO 117226 Bl

Test B.

Sphaerotheca test (cucumber) / protective Solvent: 47 parts by weight acetone Emulsifier: 3 parts by weight alkylaryl polyglycol ether.

To make a suitable preparation of the active compound, 1 part by weight of the active compound is mixed with the mentioned amounts of solvent and emulsifier and the concentrate is diluted with water, to the desired concentration. To test the protective action, the young plants are sprayed with the preparation containing the active compound at the mentioned application doses. After spraying, the coating layer is dried and the plants are inoculated with a spore suspension infested by Sphaerotheca fuligines in aqueous solution. The plants are then placed in a greenhouse at about 23 ° C and a relative atmospheric humidity of 100%. The test is evaluated 10 days after inoculation. 0% represents an efficiency that corresponds to that of the control sample, while an efficiency of 100% represents the absence of any disease. In this test, for example, the following compositions have synergistic effect compared to individual compounds.

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Table B

Sphaerotheca (cucumber) / protective test

<td>A compound / composition</td><td>Quantity applied [g / ha]</td><td>Actual / Calculated Efficiency</td>

<td>Compound 2</td><td> 10</td><td> 0</td>

<td>Compound 3</td><td> 10</td><td> 0</td>

<td>Compound 4</td><td> 10</td><td> 0</td>

<td>cyproconazole</td><td> 10</td><td> 70</td>

<td>Compound 2 + Ciproconazole</td><td> 10+ 10</td><td> 80/70</td>

<td>Compound 3 + Ciproconazole</td><td> 10+ 10</td><td> 90/70</td>

<td>Compound 4 + Ciproconazole</td><td> 10+10</td><td> 90/70</td>

<td>Compound 1</td><td> 500</td><td> 0</td>

<td></td><td> 10</td><td> 0</td>

<td>Compound 2</td><td> 500</td><td> 0</td>

<td>Compound 4</td><td> 500</td><td> 0</td>

<td></td><td> 10</td><td> 0</td>

<td>fenpiclonil</td><td> 500</td><td> 50</td>

<td>fludioxonil</td><td> 500</td><td> 70</td>

<td>Compound 1 + Fenpiclonil</td><td> 500 + 500</td><td> 95/50</td>

<td>Compound 2 + Fenpiclonil</td><td> 500 + 500</td><td> 83/50</td>

<td>Compound 4 + Fenpiclonil</td><td> 500 + 500</td><td> 73/50</td>

<td>Compound 1 + Fludioxonil</td><td> 500 + 500</td><td> 93/73</td>

<td>Compound 4 + Fludioxonil</td><td> 500 + 500</td><td> 85/70</td>

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Test C.

Botrytis (beans) / protective test

Solvent: 47 parts by weight acetone

Emulsifier: 3 parts by weight alkylaryl polyglycol ether

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To make a suitable preparation of the active compound, 1 part by weight of the active compound is mixed with the mentioned amounts of solvent and emulsifier and the concentrate is diluted with water, to the desired concentration. To test the protective activity, the young plants are sprayed with the composition containing the active compound. After spraying the coating layer dries, 2 small pieces of agar coated with Botrytis culture the ash are placed on each leaf. The inoculated plants are placed in a dark room, at 2 ° C and with a relative atmospheric humidity of 100%. At 2 days after inoculation, the size of the lesions on the leaves is evaluated. 0% represents an efficacy that corresponds to that of the control, while an efficiency of 100% represents the absence of any disease. In this test, for example, the following compositions have synergistic effect compared to individual compounds.

Table C

Botrytis (beans) / protective test

<td>A compound / composition</td><td>Quantity applied [g / ha]</td><td>Effectiveness Real / Calculated</td>

<td>Compound 1</td><td> 500</td><td> 0</td>

<td>Compound 3</td><td> 500</td><td> 0</td>

<td>Compound 4</td><td> 500</td><td> 0</td>

<td>Compound 1</td><td> 100</td><td> 0</td>

<td></td><td> 40</td><td> 0</td>

<td>Compound 2</td><td> 100</td><td> 4</td>

<td>Compound 3</td><td> 40</td><td> □</td>

<td>Compound 4</td><td> 40</td><td> 0</td>

<td>azoxystrobin</td><td> 40</td><td> 42</td>

<td>Compound 1 + Azoxistrobin</td><td> 40 + 40</td><td> 50/42</td>

<td>Compound 3 + Azoxistrobin</td><td> 40 + 40</td><td> 50/42</td>

<td>Compound 4 + Azoxistrobin</td><td> 40 + 40</td><td> 50/42</td>

<td>Compound 1</td><td> 10</td><td> 0</td>

<td>Compound 2</td><td> 10</td><td> 0</td>

<td>Compound 3</td><td> 10</td><td> □</td>

<td>fludioxonil</td><td> 10</td><td> 40</td>

<td>Compound 1 + Fludioxonil</td><td> 10 + 10</td><td> 70/40</td>

<td>Compound 2 + Fludioxonil</td><td> 10 + 10</td><td> 83/40</td>

<td>Compound 3 + Fludioxonil</td><td> 10 + 10</td><td> 71/40</td>

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Table 1

Molecular structure and names of the compounds tested

<td>Compound</td><td>Structural formula</td>

<td>Compound 1 according to the invention</td><td>^{C |}— ^N 7Ί 'ro₂nh</td>

<td>Compound 2 according to the invention</td><td>FV^NNO,</td>

<td>Compound 3 according to the invention</td><td>N^J N ~ -i NC</td>

<td>Compound 4 according to the invention</td><td>H, &lt;T N / A^NNO,</td>

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

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Table 1 [continued]

<td>Compound</td><td>Structural formula</td>

<td>triadimenol</td><td>₃(H, C) C^H0 \</td>

<td>fludioxonil</td><td> /^CNV</td>

<td>azoxystrobin</td><td>CN HjCO ^ Jț ^ OCH,</td>

<td>kresoxim</td><td>CH. (W? A</td>

<td>triazoxide</td><td>CrY</td>

Test A '.

Fusarium culmorum test (grain / seed treatment

The active compounds are applied in powder form for seed treatment. They are obtained by mixing the active compound with rock flour which ensures a uniform distribution on the seed surface. For treating the seeds, the infected seeds together with the preparation containing the active compound in powder form are stirred for 3 minutes in a closed glass flask. The wheat is sown in a standard soil, at 2 x 1OO grains, at a depth of 1 cm and kept in a greenhouse, at a temperature of about 18 ° C and a relative atmospheric humidity of about 95% in the trays. with seeds that receive light, for 15 hours a day. About 3 weeks after planting, the symptoms of the plants are evaluated. 0% represents an efficacy that corresponds to that of the control, while an efficiency of 100% indicates the absence of any disease. In this test, the following compositions have a synergistic effect compared to the individual compounds.

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Table A *

Pests fungi for plants

Fusarium culmorum test (grain / seed treatment

<td>A compound / composition</td><td>Quantity applied [mg / kg seed]</td><td>Effectiveness</td>

<td>Compound 1</td><td> 75</td><td> 0</td>

<td>Compound 2</td><td> 75</td><td> 0</td>

<td>Compound 3</td><td> 75</td><td> 0</td>

<td>Compound 4</td><td> 75</td><td> 0,5</td>

<td>triadimenol</td><td> 75</td><td> 13,5</td>

<td>fludioxanil</td><td> 75</td><td> 0</td>

<td>cyproconazole</td><td> 75</td><td> 1</td>

<td>Compound 1 + ciproconazole</td><td> 37,5 + 37,5</td><td> 34,5</td>

<td>Compound 2 + triadimenol</td><td> 37,5 + 37,5</td><td> 30,5</td>

<td>Compound 2 + fludioxonil</td><td> 37,5 + 37,5</td><td> 38,5</td>

<td>Compound 3 + triadimenol</td><td> 37,5 + 37,5</td><td> 26,5</td>

<td>Compound 3 + fludioxonil</td><td> 37,5 + 37,5</td><td> 25,5</td>

<td>Compound 3 + ciproconazole</td><td> 37,5 + 37,5</td><td> 51,5</td>

<td>Compound 4 + ciproconazole</td><td> 37,5 + 37,5</td><td> 22</td>

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1515

1520

Test B '.

Puccinia (wheat) / protective test

Solvent: 25 parts by weight N, N-dimethylacetamide Emulsifier: 0.6 parts by weight alkylaryl polyglycol ether.

To make a suitable preparation of the active compound, 1 part by weight of the active compound or active composition is mixed with the mentioned amounts of solvent and emulsifier and the concentrate diluted with water to the desired concentration as a commercially available composition. The active composition is diluted with water to the desired concentration. To test the protective action the young plants are sprayed with the preparation of the active compound at the mentioned application doses. After spraying, the coating layer dries, and the plants are sprayed with a spore suspension of Puccinia recondita. Plants are kept 48 hours in an incubation chamber, at 20 ° C and a relative atmospheric humidity of 100%. The plants are kept in a greenhouse, at a temperature of about 20 ° C and a relative atmospheric humidity of about 80% to initiate the development of rust pustules. The test is evaluated 10 days after inoculation. 0% represents an efficacy that corresponds to that of the control, while an efficiency of 100% represents the absence of any disease. For example, in this test the following compositions have a synergistic effect compared to the individual compounds.

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Table B '

Poisonous fungi for plants Puccinia (wheat) / protective test

<td>Compound / Composition</td><td>Quantity applied [q / ha]</td><td>Effectiveness</td>

<td>Compound 1</td><td> 62,5</td><td> 13</td>

<td>Compound 2</td><td> 18,75</td><td> 0</td>

<td>Compound 3</td><td> 62,5</td><td> 0</td>

<td>Compound 4</td><td> 1,875</td><td> 0</td>

<td>triadimenol</td><td> 18,75</td><td> 13</td>

<td>azoxystrobin</td><td> 1,875</td><td> 75</td>

<td>Compound 2 + triadimenol</td><td> 9,375 + 9,375</td><td> 63</td>

<td>Compound 4 + azoxystrobin</td><td> 0,9375 + 0,9375</td><td> 94</td>

Test C '.

Test Pyreno phora teres (barley] / Protective Solvent: 25 parts by weight N, N-dimethylacetamide Emulsifier: 0.6 parts by weight alkylaryl polyglycol ether.

To make a suitable preparation of the active compound, 1 part by weight of the active compound or active composition is mixed with the mentioned amounts of solvent and emulsifier and the concentrate is diluted with water to the desired concentration, or until a commercially available composition or composition is obtained. The active mixture is diluted with water at the desired concentration. In order to test the protective action, the young plants are sprayed with the preparation of the active compound at the mentioned application doses. After spraying, the coating layer dries, and the plants are sprayed with a spore suspension of Pyrenophora teres. Plants are kept for 48 hours in an incubator, at 2 ° C and 100% relative atmospheric humidity. The plants are kept in a greenhouse, at a temperature of about 2 ° C and a relative atmospheric humidity of about 80%. The test is evaluated 7 days after inoculation. □% represents an efficiency that corresponds to that of the control, while an efficiency of 100% represents the absence of any disease.

Table C '

Pests fungi for plants Test Pyrenophora teres (barley) / protection

<td>Compound / Composition</td><td>Quantity applied</td><td>[Q / hal</td><td>Effectiveness</td>

<td>Compound 1</td><td> 62,5</td><td></td><td> 0</td>

<td></td><td> 18,75</td><td></td><td> 20</td>

<td>Compound 2</td><td> 62,5</td><td></td><td> 0</td>

<td></td><td> 18,75</td><td></td><td> 20</td>

<td>Compound 3</td><td> 62,5</td><td></td><td> 0</td>

<td></td><td> 18,76</td><td></td><td> 20</td>

<td>Compound 4</td><td> 62,5</td><td></td><td> 20</td>

<td></td><td> 18,75</td><td></td><td> 40</td>

<td>triadimenol</td><td> 18,75</td><td></td><td> 40</td>

<td>triazoxide</td><td> 62,5</td><td></td><td> 40</td>

<td>azoxystrobin</td><td> 18,75</td><td></td><td> 0</td>

<td>kresoxim</td><td> 62,5</td><td></td><td> 0</td>

<td>Compound 1 + triazoxide</td><td> 31,25 + 31,25</td><td></td><td> 60</td>

<td>Compound 1 + Azoxistrobin</td><td> 9,375 + 9,375</td><td></td><td> 70</td>

<td>Compound 3 + triadimenol</td><td> 9,375 + 9,375</td><td></td><td> 60</td>

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1595

Table [continued]

<td>A compound / composition</td><td>Quantity applied</td><td>[G / ha]</td><td>Effectiveness</td>

<td>Compound 3 + azoxystrobin</td><td> 9,375 + 9,375</td><td></td><td> 80</td>

<td>Compound 2 + azoxystrobin</td><td> 9,375 + 9,375</td><td></td><td> 60</td>

<td>Compound 2 + triazoxide</td><td> 31,25 + 31,25</td><td></td><td> 70</td>

<td>Compound 4 + azoxystrobin</td><td colspan="2"> 9,375 + 9,375</td><td> 70</td>

<td>Compound 4 + crescoxymethyl</td><td colspan="2"> 31,25 + 31,25</td><td> 60</td>

1600

Test D *.

Erysiphe test (barley) / protection

Solvent: 25 parts by weight N, N-dimethylacetamide Emulsifier: 0.6 parts by weight alkylaryl polyglycol ether.

To make a suitable preparation of the active compound, 1 part by weight of the active compound or active composition is mixed with said amounts of solvent and emulsifier and the concentrate diluted with water to the desired concentration, or to a compound in a commercially available form or the desired composition is diluted with water to the desired concentration. To test the protective action the young plants are sprayed with the preparation of the active compound at the mentioned application doses.

After spraying, the coating layer dries, and the plants are dusted with spores of Erysiphe graminis f. Sp. hordei. The plants are kept in a greenhouse, at a temperature of about 20 ° C and a relative atmospheric humidity of about 80% to initiate the development of mold pustules. The test is evaluated 10 days after inoculation. 0% represents an efficacy that corresponds to that of the control, while an efficiency of 100% represents the absence of any disease.

1605

1610

1615

1620

Table D '

Pests fungi for plants Erysiphe test (barley) / protection

<td>A compound / composition</td><td>Quantity applied [g / ha]</td><td>Effectiveness</td>

<td>Compound 1</td><td> 62,5</td><td> 17</td>

<td>Compound 2</td><td> 62,5</td><td> 0</td>

<td>Compound 3</td><td> 62,5</td><td> 0</td>

<td></td><td> 18, 75</td><td> 0</td>

<td>Compound 4</td><td> 62,5</td><td> 33</td>

<td></td><td> 18,75</td><td> 0</td>

<td>kresoxim</td><td> 62,5</td><td> 0</td>

<td>compound 1 + growthoxymethyl</td><td> 31,25 + 31,25</td><td> 67</td>

<td>compound 3 + crescoxymethyl</td><td> 31,25 + 31,25</td><td> 67</td>

<td>compound 2 + crescoxymethyl</td><td> 31,25 + 31,25</td><td> 75</td>

<td>compound 4 + crescoxymethyl</td><td> 31,25 + 31,25</td><td> 67</td>

1625

1630

1635

The E test.

Erysiphe test (wheat) / protective Solvent: 25 parts by weight N, N-dimethylacetamide Emulsifier: 0.6 parts by weight alkylaryl polyglycol ether

To make a suitable preparation of the active compound, 1 part by weight of the active compound or active composition is mixed with the mentioned amounts of solvent and emulsifier and the concentrate diluted with water to the desired concentration or a commercially available formulation of the active compound or composition. dilute with water to the desired concentration.

1640

RO 117226 Bl

In order to test the protective action, the young plants are sprayed with the preparation of the active compound at the mentioned application doses. After spraying, the coating layer dries, and the plants are dusted with spores by Erysiphe graminis f.sp.tritici.

The plants are kept in a greenhouse, at a temperature of about 2 ° C and a relative atmospheric humidity of about 80% to initiate the development of mold pustules. The test is evaluated 7 days after inoculation. 0% represents an efficacy that corresponds to that of the control, while an efficiency of 100% represents the absence of any disease.

Table E *

Pests fungi for plants Erysiphe test [wheat] / protection

<td>A compound / composition</td><td>Quantity applied [g / ha]</td><td>Effectiveness</td>

<td>Compound 1</td><td> 62,5</td><td> 0</td>

<td></td><td> 6,25</td><td> 0</td>

<td>Compound 3</td><td> 62,5</td><td> 0</td>

<td></td><td> 18,75</td><td> 0</td>

<td>Compound 4</td><td> 62,5</td><td> 14</td>

<td></td><td> 18,75</td><td> 14</td>

<td>azoxystrobin</td><td> 62,5</td><td> 57</td>

<td>kresoxim</td><td> 62,5</td><td> 79</td>

<td></td><td> 18,75</td><td> 43</td>

<td>compound 1 + azoxystrobin</td><td> 31,25 + 31,25</td><td> 79</td>

<td>compound 3 + crescoxymethyl</td><td> 31,25 + 31,25</td><td> 93</td>

<td></td><td> 9,375 + 9,375</td><td> 71</td>

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1670

Table 1

Molecular structure and names of the compounds tested

<td>Compound</td><td>Structural formula</td>

<td>Compound 1 according to the invention</td><td>HN ^ / CH₃ⁿ^ No₂</td>

<td>Compound 2 according to the invention</td><td>^NNS NC</td>

<td>Compound 3 according to the invention</td><td>H, C ci-XX ^^NY '^CH’ ⁿ^ No₂</td>

<td>kresoxim</td><td>h₃co.A_nXoch₃ 0</td>

<td>cyproconazole</td><td>TOH</td>

1675

1680

1685

1690

1695

1700

RO 117226 Bl

Table 1 (continued)

<td>Compound</td><td>Structural formula</td>

<td>triadimenol</td><td>(H₃C) C^H0 Τ '</td>

<td>fludioxonil</td><td>/ -α ' CN OH</td>

<td>TMTD</td><td>s . CH. H₃C CH₃³</td>

<td>fenpiclonil</td><td>but^{c |}CN o</td>

<td>metalaxyl</td><td>Η, Ο J \ ° CH,</td>

<td>tolylfluanid</td><td>D H, C</td>

<td>azoxystrobin</td><td>N ^ N CN A</td>

Test A ”.

The Phaedon larvae test

Solvent: 7 parts by weight dimethylformamide

Emulsifier: 1 part by weight alkylaryl polyglycolether

To make a suitable preparation of the active compound, 1 part by weight of the active compound is mixed with the mentioned amounts of solvent and emulsifier and the concentrate is diluted with water to the desired concentration.

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1750

The cabbage leaves (Brassica oleracea) are treated by immersion in the preparation of the active compound at the desired concentration and are infested with larvae of the mustard beetle, [Phaedon cochleariae], when the leaves are still moist. After a specified period of time the percentage of mortality was determined 100% show that all cockroach larvae are killed, 0% mean that none of the cockroach's larvae were killed. In this test, the following compositions have a synergistic effect compared to the individual compounds.

1755

Table A "(Insect Pests)

The Phaedon larvae test

<td>Active compound / Composition</td><td>Concentration of active compound / composition, in%</td><td>Mortality, in%</td>

<td>Compound 1</td><td> 0,00016</td><td> 20</td>

<td>kresoxim</td><td> 0,1</td><td> 0</td>

<td>Compound 1 + growth oxide</td><td> 0,00016 + 0,1</td><td> 75</td>

<td>Compound 2</td><td> 0,0008</td><td> 40</td>

<td>kresoxim</td><td> 0,1</td><td> 0</td>

<td>cyproconazole</td><td> 0,004</td><td> 10</td>

<td>Compound 1 + growthoxymethyl</td><td> 0,0008 + 0,1</td><td> 95</td>

<td>Compound 2 + ciproconazole</td><td> 0,0008 + 0,004</td><td> 95</td>

<td>Compound 3</td><td> 0,0008</td><td> 10</td>

<td>triadimenol</td><td> 0,02</td><td> 20</td>

<td>fludioxonil</td><td> 0,02</td><td> 0</td>

<td>TMTD</td><td> 0,1</td><td> 0</td>

<td>cyproconazole</td><td> 0,004</td><td> 10</td>

<td>Compound 3+ triadimenol</td><td> 0,0008 + 0,02</td><td> 100</td>

<td>Compound 3+ fluodioxonil</td><td> 0,0008 + 0,02</td><td> 100</td>

<td>Compound 3+ TMDT</td><td> 0,0008 + 0,1</td><td> 80</td>

<td>Compound 3+ ciproconazole</td><td> 0,0008 + 0,004</td><td> 80</td>

1760

1765

1770

1775

Test B ”.

The Plutella test

Solvent: 7 parts by weight dimethylformamide Emulsifier: 1 part by weight alkylaryl polyglycerol.

To make a suitable preparation of the active compound, 1 part by weight of the active compound is mixed with the mentioned amounts of solvent and emulsifier and the concentrate is diluted with water to the desired concentration. The cabbage leaves, (Brassica oleracea], are treated by immersion in the preparation of the active compound at the desired concentration and are infested with the hawks of the diamond-black moth (Plutella maculipennis), when the leaves are still moist.

After a specified period of time the percentage of mortality was determined. 100% indicates that all omissions were killed; 0% indicate that no one was killed. In this test the following compositions have synergistic effect compared to the individual compounds.

1780

1785

1790

RO 117226 Bl

Table B "(Insect pests)

Plutella xylostella test

<td>Active compound / Composition</td><td>Concentration of active compound / composition, in%</td><td>Mortality, in%</td>

<td>Compound 1</td><td> 0,0008</td><td> 0</td>

<td>metalaxyl</td><td> 0,1</td><td> 0</td>

<td>Compound 1 + metalaxyl</td><td> 0,0008 + 0,1</td><td> 100</td>

<td>Compound 2</td><td> 0,004</td><td> 60</td>

<td>pencycuron</td><td> 0,1</td><td> 0</td>

<td>tolylfluanid</td><td> 0,02</td><td> 0</td>

<td>fenpiclonil</td><td> 0,1</td><td> 0</td>

<td>cyproconazole</td><td> 0,004</td><td> 0</td>

<td>Compound 2 + pencicuron</td><td> 0,004 + 0,1</td><td> 10</td>

<td>Compound 2 + tolylfluanide</td><td> 0,004 + 0,02</td><td> 90</td>

<td>compound 2 + fenpiclonil</td><td> 0,004 + 0,1</td><td> 100</td>

<td>compound 2 + ciproconazole</td><td> 0,004 + 0,004</td><td> 100</td>

<td>compound 2</td><td> 0,0008</td><td> 0</td>

<td>TMTD</td><td> 0,1</td><td> 0</td>

<td>compound 2 + TMTD</td><td> 0,0008 + 0,1</td><td> 65</td>

<td>compound 3</td><td> 0,004</td><td> 60</td>

<td>metalaxyl</td><td> 0,1</td><td> 0</td>

<td>compound 3 + metalaxyl</td><td> 0,004 + 0,1</td><td> 100</td>

<td>compound 3</td><td> 0,0008</td><td> 0</td>

Test C ".

The Spodoptera frugiperda test

Solvent: 7 parts by weight dimethylformamide

Emulsifier: 1 part by weight alkylaryl polyglycolether

To make a suitable preparation of the active compound, 1 part by weight of the active compound is mixed with the mentioned amounts of solvent and emulsifier and the concentrate is diluted with water to the desired concentration.

The cabbage leaves (Brassica oleracea) are treated by immersion in the preparation of active compound at the desired concentration and are infested with worms of the worm Spodoptera frugiperda, as long as the leaves are still moist. After a specified period of time, the percentage of mortality was determined. At a percentage, 100% of all homicides are killed, and a percentage of 0% indicates that none of the homicides has been killed.

In this test, for example, the following compositions have synergistic effect compared to individual compounds.

RO 117226 Bl

1835

Table C "(Insect pests)

The Spodoptera frugiperda test

<td>Active compound / Composition</td><td>Concentration of active compound / composition, in%</td><td>Mortality, in%</td>

<td>Compound 3</td><td> 0,004</td><td> 45</td>

<td>fludioxonil</td><td> 0,02</td><td> 0</td>

<td>TMTD</td><td> 0,1</td><td> 20</td>

<td>metalaxyl</td><td> 0,1</td><td> 20</td>

<td>compound 3 + fludioxonil</td><td> 0,004 + 0,02</td><td> 100</td>

<td>compound 3 + TMTD</td><td> 0,004 + 0,1</td><td> 100</td>

<td>compound 3 + metalaxyl</td><td> 0,004 + 0,1</td><td> 100</td>

1840

1845

Test D "

The Heliothis virescens test

Solvent: 25 parts by weight N, N- dimethylacetamide Emulsifier: 1 part by weight alkylaryl polyglycol ether

To make a suitable preparation of the active compound, 1 part by weight of the active compound or active composition is mixed with the mentioned amounts of solvent and emulsifier and the concentrate diluted with water to the desired concentration. Soybean shoots, [Glycine max], are treated by immersion in the preparation of the active compound at the desired concentration and are infested with Heliothis virescens omics when the leaves are still moist. After a specified period of time the percentage mortality is determined. The percentage, 100%, shows that all the caterpillars are killed, and one percent, 0% show that no homicides were killed. In this test, the compositions in the following table have synergistic effect.

1850

1855

1860

Table D "(Insect pests)

The Heliothis virescens test

<td>Active compound / Composition</td><td>Concentration of active compound / composition, in%</td><td>Mortality, in%</td>

<td>Compound 1</td><td> 0,00010</td><td> 50</td>

<td>azoxystrobin</td><td> 0,0008</td><td> 0</td>

<td>Compound 1 + azoxystrobin</td><td> 0,00016 + 0,0008</td><td> 100</td>

<td>Compound 2</td><td> 0,00016</td><td> 15</td>

<td>tolyfluanid</td><td> 0,02</td><td> 0</td>

<td>cyproconazole</td><td> 0,004</td><td> 0</td>

<td>compound 2 + tolifluanide</td><td> 0,00016 + 0,02</td><td> 85</td>

<td>compound 2 + ciproconazole</td><td> 0,00016 + 0,004</td><td> 100</td>

1865

1870

RO 117226 Bl

Test E.

The text I do not accept

Solvent: 7 parts by weight dimethylformamide

Emulsifier: 1 part by weight alkylaryl polyglycol ether

To make a suitable preparation of the active compound, 1 part by weight of the active compound is mixed with the mentioned amounts of solvent and extractant and the concentrate is diluted with water to the desired concentration.

The rice seedlings [Oryza sativa] are treated by immersion in the preparation containing the active compound at the desired concentration and infested with leaf fleas, [Nehotettix cincticeps], when the seedlings are still wet. After a specified period of time the percentage mortality is determined. A percentage of 100% indicates that all fleas were killed, and 0% indicates that none of the fleas were killed. In this test the compositions presented in the following table have synergistic effect.

Table E "(Insect pests)

The text I do not accept

<td>Active compound / Composition</td><td>Concentration of active compound / composition, in%</td><td>Mortality, in%</td>

<td>Compound 1</td><td> 0,00000128</td><td> 0</td>

<td>metalaxyl</td><td> 0,1</td><td> 0</td>

<td>compound 1 + metalaxyl</td><td> 0,00000128 + 0,1</td><td> 85</td>

<td>compound 2</td><td> 0,00016</td><td> 35</td>

<td></td><td> 0,000032</td><td> 0</td>

<td>tolylfluanid</td><td> 0,02</td><td> 0</td>

<td>fludioxonil</td><td> 0,02</td><td> 0</td>

<td>TMTD</td><td> 0,1</td><td> 0</td>

<td>metalaxyl</td><td> 0,1</td><td> 0</td>

<td>compound 2 + tolylfluanide</td><td> 0,000032 + 0,02</td><td> 70</td>

<td>compound 2 + fludioxonil</td><td> 0,00016 + 0,02</td><td> 90</td>

<td>compound 2 + TMTD</td><td> 0,000032 + 0,1</td><td> 45</td>

<td>compound 2 + metalaxyl</td><td> 0,00016 + 0,1</td><td> 100</td>

Test F ".

Myzus test

Solvent: 7 parts by weight dimethylformamide Emulsifier: 1 part by weight alkylaryl polyglycol ether.

To obtain a product containing the active compound, 1 part by weight of the active compound is mixed with the mentioned amounts of solvent and emulsifier and the concentrate is diluted with water to the desired concentration. Cabbage leaves, [Brassica oleracea], heavily infested with aphids, [Myzus persicae], are treated by immersion in the preparation of the active compound at the desired concentration. After a period of time the percentage mortality is determined. The percentage, 100% indicates that all aphids were killed, and 0% indicate that none of the aphids were killed. In this test the compositions presented in the following table have synergistic effect.

RO 117226 Bl

1920

Table F "(Insect pests)

Myzus test

<td>Active compound / Composition</td><td>Concentration of active compound / composition, in%</td><td>Mortality, in%</td>

<td>Compound 2</td><td> 0,00016</td><td> 25</td>

<td>fenpiclonil</td><td> 0,1</td><td> 0</td>

<td>metalaxyl</td><td> 0,1</td><td> 0</td>

<td>compound 2 + fenpiclonil</td><td> 0,00016 + 0,1</td><td> 80</td>

<td>compound 2 + metalaxyl</td><td> 0,000 + 0,1</td><td> 90</td>

<td>compound 3</td><td> 0,004</td><td> 60</td>

<td></td><td> 0,0008</td><td> 5</td>

<td></td><td> 0,00016</td><td> 5</td>

<td>fenpiclonil</td><td> 0,1</td><td> 0</td>

<td>fludioxonil</td><td> 0,02</td><td> 0</td>

<td>TMTD</td><td> 0,1</td><td> 0</td>

<td>metalaxyl</td><td> 0,1</td><td> 0</td>

<td>kresoxim</td><td> 0,1</td><td> 0</td>

<td>azoxitrobin</td><td> 0,0008</td><td> 0</td>

<td>compound 3 + fenpiclonil</td><td> 0,00016 + 0,1</td><td> 90</td>

<td>compound 3 + fludioxonil</td><td> 0,004 + 0,02</td><td> 100</td>

<td>compound 3 + TMTD</td><td> 0,004 + 0,1</td><td> 100</td>

<td>compound 3 + metalaxyl</td><td> 0,0008 + 0,1</td><td> 100</td>

<td>compound 3 + crescoxymethyl</td><td> 0,004 + 0,1</td><td> 100</td>

<td>compound 3 + azoxystrobin</td><td> 0,004 + 0,0008</td><td> 100</td>

1925

1930

1935

1940

1945

RO 117226 Bl

1950

1955

1960

1965

1970

1975

It would be the 4th test

Table 1

Molecular structure and names of the compounds tested

<td>Compound</td><td>Structural formula</td>

<td>Compound 1 according to the invention</td><td>HN- ^ z^N^ CH₃ⁿ-no₂</td>

<td>Compound 2 according to the invention</td><td>^N Z3 NS NC</td>

<td>Compound 3 according to the invention</td><td>H, C N — Λ «Λ? —V '™'^NNO₂</td>

<td>kresoxim</td><td>h₃co_xX_{n /}och₃a</td>

<td>cyproconazole</td><td>A. _CH₃Toh Jk U.JL O ^ClN</td>

1980

RO 117226 Bl

1985

Table 1 (continued)

<td>Compound</td><td>Structural formula</td>

<td>triadimenol</td><td>(H, C&gt; C H °</td>

<td>fludioxonil</td><td>rO^F- CN It might be</td>

<td>TMTD</td><td>S .S ^ JL -CH, s' ^ N ^s_, N_K CH H, C CH, ¹</td>

<td>fenpiclonil</td><td>But CN A</td>

<td>metalaxyl</td><td>W / H, that CH,</td>

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

<td>azoxystrobin</td><td>QXW CN Η, ΟΟ ^ ΧζΟΟΗ, A</td>

1990

1995

2000

2005

2010

Test A '”

The Diabrotica balteata-larvae test

Solvent: 4 parts by weight acetone

Emulsifier: 1 part by weight alkylaryl polyglycolether

To make a suitable compound containing the active compound, 1 part by weight of the active compound is mixed with the mentioned amounts of solvent and emulsifier and the concentrate is diluted with water to the desired concentration. The preparation thus obtained containing the active compound is mixed with the soil. The concentration of active compound in the preparation does not matter, the decisive parameter being the amount of active compound per unit volume of soil. This parameter is expressed in ppm (mg / l).

Fill the pots with treated soil and top five corn kernels to germinate. Next, keep the pots in a greenhouse at 2 ° C. After two days the test insects are added. After another 7 days the effectiveness of the protection is determined. The efficiency is calculated from the number of maize plants grown. The following table shows the active compounds or compositions, their application doses and the results obtained.

2015

2020

2025

RO 117226 Bl

Table A / T

Root insects

Diabrotic balteata larvae

<td>A compound / composition</td><td>Quantity applied [ppm]</td><td>effectiveness</td>

<td>Compound 1</td><td> 1,25</td><td> 90</td>

<td></td><td> 0,60</td><td> 90</td>

<td></td><td> 0,30</td><td> 40</td>

<td>triadimenol</td><td> 20,00</td><td> 0</td>

<td>tolylfluanid</td><td> 20,00</td><td> 0</td>

<td>fenpiclonil</td><td> 20,00</td><td> □</td>

<td>fludioxonil</td><td> 20,00</td><td> 0</td>

<td>azoxystrobin</td><td> 20,00</td><td> 0</td>

<td>metalaxyl</td><td> 20,00</td><td> 0</td>

<td>cyproconazole</td><td> 20,00</td><td> 0</td>

<td>kresoxim</td><td> 20,00</td><td> 0</td>

<td>TMTD</td><td> 20,00</td><td> 0</td>

<td>Compound 1 + triadimenol</td><td> 1,25 + 20,00</td><td> 100</td>

<td></td><td> 0,60 + 20,00</td><td> 20</td>

<td></td><td> 0,30 + 20,00</td><td> 20</td>

<td>Compound 1 + tolylfluanide</td><td> 1,25 + 20,00</td><td> 80</td>

<td></td><td> 0,60 + 20,00</td><td> 50</td>

<td></td><td> 0,30 + 20,00</td><td> 0</td>

<td>Compound 1 + fenpiclonil</td><td> 1,25 + 20,00</td><td> 80</td>

<td></td><td> 0,60 + 20,00</td><td> 80</td>

<td></td><td> 0,30 + 20,00</td><td> 30</td>

<td>Compound 1 + fludioxonil</td><td> 1,25 + 20,00</td><td> 30</td>

<td></td><td> 0,60 + 20,00</td><td> 30</td>

<td></td><td> 0,30 + 20,00</td><td> 0</td>

<td>Compound 1 + azoxystrobin</td><td> 1,25 + 20,00</td><td> 90</td>

<td></td><td> 0,60 + 20,00</td><td> 0</td>

<td></td><td> 0,30 + 20,00</td><td> 0</td>

<td>Compound 1 + metalaxyl</td><td> 1,25 + 20,00</td><td> 80</td>

<td></td><td> 0,60 + 20,00</td><td> 80</td>

<td></td><td> 0,30 + 20,00</td><td> 30</td>

<td>compound 1 + ciproconazole</td><td> 1,25 + 20,00</td><td> 90</td>

<td></td><td> 0,60 + 20,00</td><td> 50</td>

<td></td><td> 0,30 + 20,00</td><td> 0</td>

<td>Compound 1 + growthoxymethyl</td><td> 1,25 + 20,00</td><td> 100</td>

<td></td><td> 0,60 + 20,00</td><td> 30</td>

<td></td><td> 0,30 + 20,00</td><td> 0</td>

<td>Compound 1 + TMTD</td><td> 1,25 + 20,00</td><td> 100</td>

<td></td><td> 0,60 + 20,00</td><td> 90</td>

<td></td><td> 0,30 + 20,00</td><td> 0</td>

RO 117226 Bl

2075

Table A ”* / 2

Root insects

Diabrotic balteata larvae

<td>A compound / composition</td><td>Quantity applied [ppm]</td><td>effectiveness</td>

<td>Compound 2</td><td> 5,00</td><td> 90</td>

<td></td><td> 2,50</td><td> 40</td>

<td></td><td> 1,25</td><td> 0</td>

<td>triadimenol</td><td> 20,00</td><td> 0</td>

<td>tolylfluanid</td><td> 20,00</td><td> 0</td>

<td>fenpiclonil</td><td> 20,00</td><td> 0</td>

<td>fludioxonil</td><td> 20,00</td><td> 0</td>

<td>azoxystrobin</td><td> 20, 00</td><td> 0</td>

<td>metalaxyl</td><td> 20,00</td><td> 0</td>

<td>cyproconazole</td><td> 20,00</td><td> 0</td>

<td>kresoxim</td><td> 20,00</td><td> 0</td>

<td>TMTD</td><td> 20,00</td><td> 0</td>

<td>Compound 2 + triadimenol</td><td> 5,00 + 20,00</td><td> 90</td>

<td></td><td> 2,50 + 20,00</td><td> 50</td>

<td></td><td> 1,25 + 20,00</td><td> 10</td>

<td>Compound 2 + tolylfluanide</td><td> 5,00 + 20,00</td><td> 100</td>

<td></td><td> 2,50 + 20,00</td><td> 100</td>

<td></td><td> 1,25 + 20,00</td><td> 80</td>

<td>Compound 2 + fenpiclonil</td><td> 5,00 + 20,00</td><td> 100</td>

<td></td><td> 2,50 + 20,00</td><td> 100</td>

<td></td><td> 1,25 + 20,00</td><td> 70</td>

<td>Compound 2 + fludioxonil</td><td> 5,00 + 20,00</td><td> 100</td>

<td></td><td> 2,50 + 20,00</td><td> 100</td>

<td></td><td> 1,25 + 20,00</td><td> 90</td>

<td>Compound 2 + azoxystrobin</td><td> 5,00 + 20,00</td><td> 100</td>

<td></td><td> 2,50 + 20,00</td><td> 100</td>

<td></td><td> 1,25 + 20,00</td><td> 0</td>

<td>Compound 2 + metalaxyl</td><td> 5,00 + 20,00</td><td> 90</td>

<td></td><td> 2,50 + 20,00</td><td> 90</td>

<td></td><td> 1,25 + 20,00</td><td> 0</td>

<td>Compound 2 + ciproconazole</td><td> 5,00 + 20,00</td><td> 90</td>

<td></td><td> 2,50 + 20,00</td><td> 70</td>

<td></td><td> 1,25 + 20,00</td><td> 0</td>

<td>Compound 2 + crescoxymethyl</td><td> 5,00 + 20,00</td><td> 100</td>

<td></td><td> 2,50 + 20,00</td><td> 100</td>

<td></td><td> 1,25 + 20,00</td><td> 70</td>

<td>Compound 2 + TMTD</td><td> 5,00 + 20,00</td><td> 100</td>

<td></td><td> 2,50 + 20,00</td><td> 90</td>

<td></td><td> 1,25+ 20,00</td><td> 60</td>

2080

2085

2090

2095

2100

2105

2110

2115

RO 117226 Bl

Table A / 3 '

Root insects

Diabrotic balteata larvae

<td>A compound / composition</td><td>Quantity applied [ppm]</td><td>effectiveness</td>

<td>Compound 3</td><td> 2,50</td><td> 100</td>

<td></td><td> 1,25</td><td> 80</td>

<td></td><td> 0,60</td><td> 40</td>

<td>triadimenol</td><td> 20,00</td><td> 0</td>

<td>tolylfluanid</td><td> 20,00</td><td> 0</td>

<td>fenpiclonil</td><td> 20,00</td><td> 0</td>

<td>fludioxonil</td><td> 20,00</td><td> 0</td>

<td>azoxystrobin</td><td> 20,00</td><td> 0</td>

<td>metalaxyl</td><td> 20,00</td><td> 0</td>

<td>cyproconazole</td><td> 20,00</td><td> 0</td>

<td>kresoxim</td><td> 20,00</td><td> 0</td>

<td>TMTD</td><td> 20,00</td><td> 0</td>

<td>Compound 3 + triadimenol</td><td> 2,50 + 20,00</td><td> 70</td>

<td></td><td> 1,25 + 20,00</td><td> 50</td>

<td></td><td> 0,60 + 20,00</td><td> 0</td>

<td>Compound 3 + tolylfluanide</td><td> 2,50 + 20,00</td><td> 100</td>

<td></td><td> 1,25 + 20,00</td><td> 70</td>

<td></td><td> 0,60 + 20,00</td><td> 0</td>

<td>Compound 3 + fenpiclonil</td><td> 2,50 + 20,00</td><td> 100</td>

<td></td><td> 1,25 + 20,00</td><td> 80</td>

<td></td><td> 0,60 + 20,00</td><td> 80</td>

<td>Compound 3 + fludioxonil</td><td> 2,50 + 20,00</td><td> 80</td>

<td></td><td> 1,25 + 20,00</td><td> 60</td>

<td></td><td> 0,60 + 20,00</td><td> 30</td>

<td>Compound 3 + azoxystrobin</td><td> 2,50 + 20,00</td><td> 60</td>

<td></td><td> 1,25 + 20,00</td><td> 30</td>

<td></td><td> 0,60 + 20,00</td><td> 0</td>

<td>Compound 3 + metalaxyl</td><td> 2,50 + 20,00</td><td> 90</td>

<td></td><td> 1,25 + 20,00</td><td> 30</td>

<td></td><td> 0,60 + 20,00</td><td> 0</td>

<td>Compound 3 + ciproconazole</td><td> 2,50 + 20,00</td><td> 100</td>

<td></td><td> 1,25 + 20,00</td><td> 80</td>

<td></td><td> 0,60 + 20,00</td><td> 30</td>

<td>compound 3 + crescoxymethyl</td><td> 2,50 + 20,00</td><td> 80</td>

<td></td><td> 1,25 + 20,00</td><td> 50</td>

<td></td><td> 0,60 + 20,00</td><td> 50</td>

<td>Compound 3 + TMTD</td><td> 2,50 + 20,00</td><td> 90</td>

<td></td><td> 1,25 + 20,00</td><td> 30</td>

<td></td><td> 0,60 + 20,00</td><td> 30</td>

RO 117226 Bl

Test B '”.

Spodoptera frugiperda test Solvent: 4 parts by weight acetone Emulsifier: 1 part by weight alkylaryl polyglycolether

In order to obtain the corresponding composition containing the active compound, 1 part by weight of the active compound is mixed with the mentioned amounts of solvent and emulsifier and the concentrate is diluted with water to the desired concentration. The preparation containing the active compound is mixed in the soil. The concentration of active compound in the preparation does not matter, the decisive parameter being the amount of active compound per unit volume of soil. This parameter is expressed in ppm (mg / l). Fill the pots with the treated soil and top three corn kernels to germinate. Next, keep the pots in a greenhouse at 2 ° C. After the corn plants begin to grow above the pots, perforated boxes are placed. At 9 days after filling the pots the test insects are added. After another 5 days the effectiveness of the protection is calculated. Efficiency is calculated by comparing the percentage of plant material eaten in treated and untreated plants. A percentage of 0% shows that all plant material was eaten. 100% indicates that there are only small signs of eating compared to the untreated control sample.

The following tables show the active compounds or the compositions used, their application concentrations and the obtained results.

2165

2170

2175

2180

Table B '/ 1

Systemic activity of the root Spodoptera frugiperda test

<td>A compound / composition</td><td>Quantity applied [ppm]</td><td>effectiveness</td>

<td>Compound 1</td><td> 1,25</td><td> 100</td>

<td></td><td> 0,60</td><td> 98</td>

<td></td><td> 0,30</td><td> 50</td>

<td>triadimenol</td><td> 20,00</td><td> 0</td>

<td>fenpiclonil</td><td> 20,0</td><td> 0</td>

<td>azoxystrobin</td><td> 20,00</td><td> 0</td>

<td>metalaxyl</td><td> 20,00</td><td> 0</td>

<td>cyproconazole</td><td> 20,00</td><td> 0</td>

<td>Compound 1 + Triadimenol</td><td> 1,25 + 20,00</td><td> 100</td>

<td></td><td> 0,60 + 20,00</td><td> 80</td>

<td></td><td> 0,30 + 20,00</td><td> 50</td>

<td>Compound 1 + Fenpiclonil</td><td> 1,25 + 20,00</td><td> 100</td>

<td></td><td> 0,60 + 20,00</td><td> 90</td>

<td></td><td> 0,30 + 20,00</td><td> 80</td>

<td>Compound 1 + Azoxistrobin</td><td> 1,25 + 20,00</td><td> 100</td>

<td></td><td> 0,60 + 20,00</td><td> 80</td>

<td></td><td> 0,30 + 20,00</td><td> 0</td>

<td>Compound 1 + Metalaxyl</td><td> 1,25 + 20,00</td><td> 100</td>

<td></td><td> 0,60 + 20,00</td><td> 95</td>

<td></td><td> 0,30 + 20,00</td><td> 0</td>

<td>Compound 1 + Ciproconazole</td><td> 1,25 + 20,00</td><td> 100</td>

<td></td><td> 0,60 + 20,00</td><td> 50</td>

<td></td><td> 0,30 + 20,00</td><td> 0</td>

2185

2190

2195

2200

2205

RO 117226 Bl

Table B * / 2

The systemic activity of the root

The Spodoptera frugiperda test

<td>A compound / composition</td><td>Quantity applied [ppm]</td><td>effectiveness</td>

<td>Compound 2</td><td> 20,00</td><td> 100</td>

<td></td><td> 10,00</td><td> 50</td>

<td></td><td> 5,00</td><td> 0</td>

<td>triadimenol</td><td> 20,00</td><td> 0</td>

<td>fenpiclonil</td><td> 20,00</td><td> 0</td>

<td>azoxystrobin</td><td> 20,00</td><td> 0</td>

<td>metalaxyl</td><td> 20,00</td><td> 0</td>

<td>cyproconazole</td><td> 20,00</td><td> 0</td>

<td>Compound 2 + Triadimenol</td><td> 20,00 + 20,00</td><td> 100</td>

<td></td><td> 10,00 + 20,00</td><td> 70</td>

<td></td><td> 5,00 + 20,00</td><td> 0</td>

<td>Compound 2 + Fenpiclonil</td><td> 20,00 + 20,00</td><td> 100</td>

<td></td><td> 10,00 + 20,00</td><td> 50</td>

<td></td><td> 5,00 + 20,00</td><td> 0</td>

<td>Compound 2 + Azoxistrobin</td><td> 20,00 + 20,00</td><td> 100</td>

<td></td><td> 10,00 + 20,00</td><td> 50</td>

<td></td><td> 5,00 + 20,00</td><td> 0</td>

<td>Compound 2 + Metalaxyl</td><td> 20,00 + 20,00</td><td> 100</td>

<td></td><td> 10,00 + 20,00</td><td> 70</td>

<td></td><td> 5,00 + 20,00</td><td> 0</td>

<td>Compound 2 + Ciproconazole</td><td> 20,00 + 20,00</td><td> 100</td>

<td></td><td> 10,00 + 20,00</td><td> 50</td>

<td></td><td> 5,00+ 20,00</td><td> 0</td>

RO 117226 Bl

2240

Table B ”73

Systemic activity of the root Spodoptera frugiperda test

<td>A compound / composition</td><td>Quantity applied [ppm]</td><td>effectiveness</td>

<td>Compound 3</td><td> 2,50</td><td> 100</td>

<td></td><td> 1,25</td><td> 90</td>

<td></td><td> 0,60</td><td> 50</td>

<td>triadimenol</td><td> 20,00</td><td> 0</td>

<td>fenpiclonil</td><td> 20,0</td><td> 0</td>

<td>azoxystrobin</td><td> 20,00</td><td> 0</td>

<td>metalaxyl</td><td> 20,00</td><td> 0</td>

<td>cyproconazole</td><td> 20,00</td><td> 0</td>

<td>Compound 3 + Triadimenol</td><td> 2,50 + 20,00</td><td> 100</td>

<td></td><td> 1,25 + 20,00</td><td> 100</td>

<td></td><td> 0,60 + 20,00</td><td> 80</td>

<td>Compound 3 + Fenpiclonil</td><td> 2,50 + 20,00</td><td> 100</td>

<td></td><td> 1,25 + 20,00</td><td> 90</td>

<td></td><td> 0,60 + 20,00</td><td> 50</td>

<td>Compound 3 + Azoxistrobin</td><td> 2,50 + 20,00</td><td> 100</td>

<td></td><td> 1,25 + 20,00</td><td> 90</td>

<td></td><td> 0,60 + 20,00</td><td> 50</td>

<td>Compound 3 + Metalaxyl</td><td> 2,50 + 20,00</td><td> 100</td>

<td></td><td> 1,25 + 20,00</td><td> 90</td>

<td></td><td> 0,60 + 20,00</td><td> 50</td>

<td>Compound 3 + Ciproconazole</td><td> 2,50 + 20,00</td><td> 100</td>

<td></td><td> 1,25 + 20,00</td><td> 90</td>

<td></td><td> 0,60 + 20,00</td><td> 70</td>

<td>Compound 3 + Metalaxyl</td><td> 0,60 + 20,00</td><td> 100</td>

<td></td><td> 0,30 + 20,00</td><td> 90</td>

<td></td><td> 0,15 + 20,00</td><td> 50</td>

2245

2250

2255

2260

2265

Test C

Test Phaedon cochleariae - larvae

Solvent: 4 parts by weight acetone Emulsifier: 1 part by weight alkylaryl polyglycerol.

To obtain the composition, according to the invention, 1 part by weight of the active compound or composition is mixed with the mentioned amounts of solvent and emulsifier and the concentrate is diluted with water to the desired concentration. This composition containing the active compound is mixed with the soil. The concentration of active compound in the preparation does not matter, the decisive parameter being the amount of active compound per unit volume of soil. This parameter is expressed in ppm (mg / l).

Fill the pots with treated soil and plant the cabbage [Brassica oleracea]. After 7 days the test insects are added to the plants. After another 3 days the effectiveness of the protection is calculated. Efficiency is calculated by comparing the percentage of plant material eaten in treated and untreated plants. 0% means that all the plant material was eaten. 100% means that there are only small signs of being eaten compared to the untreated control sample.

The following tables show the active compounds or the compositions used, the application concentrations and the obtained results.

2270

2275

2280

2285

RO 117226 Bl

<td>A compound / composition</td><td>Quantity applied (ppm)</td><td>effectiveness</td>

<td>Compound 3 + Metalaxyl</td><td> 0,60 + 20,00 0,30 + 20,00 0,15 + 20,00</td><td> 100 90 50</td>

Table C '”/ 1

Root systemic activity Phaedon cochleariae-larvae test

<td>A compound / composition</td><td>Quantity applied (ppm)</td><td>effectiveness</td>

<td>Compound 1</td><td> 1,25</td><td> 100</td>

<td></td><td> 0,60</td><td> 80</td>

<td></td><td> 0,30</td><td> 50</td>

<td>triadimenol</td><td> 20,00</td><td> 0</td>

<td>fenpiclonil</td><td> 20,00</td><td> 0</td>

<td>azoxystrobin</td><td> 20,00</td><td> 0</td>

<td>metalaxyl</td><td> 20,00</td><td> 0</td>

<td>Compound 1 + Triadimenol</td><td> 1,25 + 20,00</td><td> 100</td>

<td></td><td> 0,60 + 20,00</td><td> 100</td>

<td></td><td> 0,30 + 20,00</td><td> 100</td>

<td>Compound 1 + Fenpiclonil</td><td> 1,25 + 20,00</td><td> 100</td>

<td></td><td> 0,60 + 20,00</td><td> 100</td>

<td></td><td> 0,30 + 20,00</td><td> 70</td>

<td>Compound 1 + Azoxistrobin</td><td> 1,25 + 20,00</td><td> 100</td>

<td></td><td> 0,60 + 20,00</td><td> 90</td>

<td></td><td> 0,30 + 20,00</td><td> 50</td>

<td>Compound 1 + Metalaxyl</td><td> 1,25 + 20,00</td><td> 100</td>

<td></td><td> 0,60 + 20,00</td><td> 100</td>

<td></td><td> 0,30 + 20,00</td><td> 50</td>

Table C “72

Root systemic activity Phaedon cochleariae-larvae test

<td>A compound / composition</td><td>Quantity applied [ppm]</td><td>effectiveness</td>

<td>Compound 2</td><td> 10,00</td><td> 95</td>

<td></td><td> 5,00</td><td> 80</td>

<td></td><td> 2,50</td><td> 0</td>

<td>triadimenol</td><td> 20,00</td><td> 0</td>

<td>enpiclonil</td><td> 20,00</td><td> 0</td>

<td>azoxystrobin</td><td> 20,00</td><td> 0</td>

<td>metalaxyl</td><td> 20,00</td><td> 0</td>

<td>Compound 2 + Triadimenol</td><td> 10,00 + 20,00</td><td> 100</td>

<td></td><td> 5,00 + 20,00</td><td> 100</td>

<td></td><td> 2,50 + 20,00</td><td> 90</td>

<td>Compound 2 + Fenpiclonil</td><td> 10,00 + 20,00</td><td> 95</td>

<td></td><td> 5,00 + 20,00</td><td> 70</td>

<td></td><td> 2,50 + 20,00</td><td> 0</td>

<td>Compound 2 + Azoxistrobin</td><td> 10,00 + 20,00</td><td> 90</td>

<td></td><td> 5,00 + 20,00</td><td> 50</td>

<td></td><td> 2,50 + 20,00</td><td> 0</td>

<td></td><td> 2,50 + 20,00</td><td> 0</td>

<td>Compound 2 + Metalaxyl</td><td> 10,00 + 20,00</td><td> 98</td>

<td></td><td> 5,00 + 20,00</td><td> 70</td>

<td></td><td> 2,50 + 20,00</td><td> 0</td>

RO 117226 Bl

2340

Table C * “/ 3

The systemic activity of the root

The Phaedon cochleariae-larvae test

<td>A compound / composition</td><td>Quantity applied [ppm]</td><td>effectiveness</td>

<td>Compound 3</td><td> 2,50</td><td> 100</td>

<td></td><td> 1,25</td><td> 70</td>

<td></td><td>O.6O</td><td> 50</td>

<td>triadimenol</td><td> 20,00</td><td> 0</td>

<td>fenpiclonil</td><td> 20,00</td><td> 0</td>

<td>azoxystrobin</td><td> 20,00</td><td> 0</td>

<td>metalaxyl</td><td> 20,00</td><td> 0</td>

<td>Compound 3 + Triadimenol</td><td> 2,50 + 20,00</td><td> 100</td>

<td></td><td> 1,25 + 20,00</td><td> 100</td>

<td></td><td> 0,60 + 20,00</td><td> 90</td>

<td>Compound 3 + Fenpiclonil</td><td> 2,50 + 20,00</td><td> 100</td>

<td></td><td> 1,25 + 20,00</td><td> 70</td>

<td></td><td> 0,60 + 20,00</td><td> 50</td>

<td>Compound 3 + Azoxistrobin</td><td> 2,50 + 20,00</td><td> 100</td>

<td></td><td> 1,25 + 20,00</td><td> 90</td>

<td></td><td> 0,60 + 20,00</td><td> 50</td>

<td>Compound 3 + Metalaxyl</td><td> 2,50 + 20,00</td><td> 100</td>

<td></td><td> 1,25 + 20,00</td><td> 95</td>

<td></td><td> 0,60 + 20,00</td><td> 0</td>

2345

2350

2355

2360

Table C ** 74

The systemic activity of the root

The Phaedon cochleariae-larvae test

<td>A compound / composition</td><td>Quantity applied [pp m]</td><td>effectiveness</td>

<td>Compound 3</td><td> 0,60</td><td> 100</td>

<td></td><td> 0,30</td><td> 75</td>

<td></td><td> 0,15</td><td> 50</td>

<td>triadimenol</td><td> 20,00</td><td> 0</td>

<td>fenpiclonil</td><td> 20,00</td><td> 0</td>

<td>azoxystrobin</td><td> 20,00</td><td> 0</td>

<td>metalaxyl</td><td> 20,00</td><td> 0</td>

<td>Compound 3 + Triadimenol</td><td> 0,60 + 20,00</td><td> 100</td>

<td></td><td> 0,30 + 20,00</td><td> 70</td>

<td></td><td> 0,15 + 20,00</td><td> 70</td>

<td>Compound 3 + Fenpiclonil</td><td> 0,60 + 20,00</td><td> 100</td>

<td></td><td> 0,30 + 20,00</td><td> 80</td>

<td></td><td> 0,15 + 20,00</td><td> 50</td>

<td>Compound 3 t Azoxistrobin</td><td> 0,60 + 20,00</td><td> 100</td>

<td></td><td> 0,30 + 20,00</td><td> 70</td>

<td></td><td> 0,15 + 20,00</td><td> 0</td>

2365

2370

2375

2380

RO 117226 Bl

Test D '.

The Aphis fabae test

Solvent: 4 parts by weight acetone

Emulsifier: 1 part by weight alkylaryl polyglycolether.

To obtain the composition containing the active compound, 1 part by weight of the active compound is mixed with the mentioned amounts of solvent and emulsifier and the concentrate is diluted with water to the desired concentration. The preparation containing the active compound is mixed with the soil. The concentration of active compound in the preparation does not matter, the decisive parameter being the amount of active compound per unit volume of soil. This parameter is expressed in ppm (mg / l). Fill the pots with treated soil and above the soil put beans in germination. After 7 days the test insects are added to the plants. After another 7 days the effectiveness of the protection is determined. The effectiveness is calculated as the number of dead insects expressed as a percentage. 100% means that all insects have been killed. 0% means that no insect was killed. The following tables show the active compounds or the compositions used, the concentrations of acetora application and the results obtained.

Table D * 71

Root systemic activity Aphis fabae test

<td>A compound / composition</td><td>Quantity applied [ppm]</td><td>effectiveness</td>

<td>Compound 1</td><td> 1,25</td><td> 100</td>

<td></td><td> 0,60</td><td> 100</td>

<td></td><td> 0,30</td><td> 50</td>

<td>triadimenol</td><td> 20,00</td><td> 0</td>

<td>fenpiclonil</td><td> 20,00</td><td> 0</td>

<td>azoxystrobin</td><td> 20,00</td><td> 0</td>

<td>metalaxyl</td><td> 20,00</td><td> 0</td>

<td>cyproconazole</td><td> 20,00</td><td> 0</td>

<td>Compound 1 + Triadimenol</td><td> 1,25 + 20,00</td><td> 100</td>

<td></td><td> 0,60 + 20,00</td><td> 100</td>

<td></td><td> 0,30 + 20,00</td><td> 70</td>

<td>Compound 1 + Fenpiclonil</td><td> 1,25 + 20,00</td><td> 98</td>

<td></td><td> 0,60 + 20,00</td><td> 50</td>

<td></td><td> 0,30 + 20,00</td><td> 0</td>

<td>Compound 1 + Azoxistrobin</td><td> 1,25 + 20,00</td><td> 100</td>

<td></td><td> 0,60 + 20,00</td><td> 90</td>

<td></td><td> 0,30 + 20,00</td><td> 0</td>

<td>Compound 1 + Metalaxyl</td><td> 1,25 + 20,00</td><td> 90</td>

<td></td><td> 0,60 + 20,00</td><td> 0</td>

<td></td><td> 0,30 + 20,00</td><td> 0</td>

<td>Compound 1 + Ciproconazole</td><td> 1,25 + 20,00</td><td> 80</td>

<td></td><td> 0,60 + 20,00</td><td> 50</td>

<td></td><td> 0,30 + 20,00</td><td> 0</td>

RO 117226 Bl

2430

Table D * "/ 2 Systemic root activity Aphis fabae test

<td>A compound / composition</td><td>Quantity applied [ppm]</td><td>effectiveness</td>

<td>Compound 2</td><td> 0,60</td><td> 100</td>

<td></td><td> 0,30</td><td> 100</td>

<td></td><td> 0,15</td><td> 90</td>

<td>triadimenol</td><td> 20,00</td><td> 0</td>

<td>fenpiclonil</td><td> 20,00</td><td> 0</td>

<td>azoxystrobin</td><td> 20,00</td><td> 0</td>

<td>metalaxyl</td><td> 20,00</td><td> 0</td>

<td>cyproconazole</td><td> 20,00</td><td> 0</td>

<td>Compound 2 + Triadimenol</td><td> 0,60 + 20,00</td><td> 100</td>

<td></td><td> 0,30 + 20,00</td><td> 100</td>

<td></td><td> 0,15 + 20,00</td><td> 90</td>

<td>Compound 2 + Fenpiclonil</td><td> 0,60 + 20,00</td><td> 100</td>

<td></td><td> 0,30 + 20,00</td><td> 90</td>

<td></td><td> 0,15 + 20,00</td><td> 50</td>

<td>Compound 2 + Azoxistrobin</td><td> 0,60 + 20,00</td><td> 100</td>

<td></td><td> 0,30 + 20,00</td><td> 100</td>

<td></td><td> 0,15 + 20,00</td><td> 98</td>

<td>Compound 2 + Metalaxyl</td><td> 0,60 + 20,00</td><td> 100</td>

<td></td><td> 0,30 + 20,00</td><td> 100</td>

<td></td><td> 0,15 + 20,00</td><td> 70</td>

<td>Compound 2 + Ciproconazole</td><td> 0,60 + 20,00</td><td> 100</td>

<td></td><td> 0,30 + 20,00</td><td> 50</td>

<td></td><td> 0,15 + 20,00</td><td> 0</td>

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RO 117226 Bl

Table D * / 3

The systemic activity of the root

The Aphis fabae test

<td>A compound / composition</td><td>Quantity applied [ppm]</td><td>effectiveness</td>

<td>Compound 3</td><td> 0,30</td><td> 100</td>

<td></td><td> 0,15</td><td> 90</td>

<td></td><td> 0,07</td><td> 0</td>

<td>triadimenol</td><td> 20,00</td><td> 0</td>

<td>fenpiclonil</td><td> 20,00</td><td> 0</td>

<td>azoxystrobin</td><td> 20,00</td><td> 0</td>

<td>metalaxyl</td><td> 20,00</td><td> 0</td>

<td>cyproconazole</td><td> 20,00</td><td> 0</td>

<td>Compound 3 + Triadimenol</td><td> 0,30 + 20,00</td><td> 900</td>

<td></td><td> 0,15 + 20,00</td><td> 90</td>

<td></td><td> 0,07 + 20,00</td><td> 50</td>

<td>Compound 3 + Fenpiclonil</td><td> 0,30 + 20,00</td><td> 50</td>

<td></td><td> 0,15 + 20,00</td><td> 0</td>

<td></td><td> 0,07 + 20,00</td><td> 0</td>

<td>Compound 3 + Azoxistrobin</td><td> 0,30 + 20,00</td><td> 50</td>

<td></td><td> 0,15 + 20,00</td><td> 0</td>

<td></td><td> 0,07 + 20,00</td><td> 0</td>

<td>Compound 3 + Metalaxyl</td><td> 0,30 + 20,00</td><td> 0</td>

<td></td><td> 0,15 + 20,00</td><td> 0</td>

<td></td><td> 0,07 + 20,00</td><td> 0</td>

<td>Compound 3 + Ciproconazole</td><td> 0,30 + 20,00</td><td> 0</td>

<td></td><td> 0,15 + 20,00</td><td> 0</td>

<td></td><td> 0,07 + 20,00</td><td> 0</td>