CA2944940C - FUNGICIDAL ACTIVE COMPOUND COMBINATIONS

4 claims: 3 independent, 1 dependent

1
CLAIMS:1 · A synergistic fungicidal composition, comprising an active compound combination consisting of: [A] 2-[2-(l-chlorocyclopropyl)-3-(2-chlorophenyl)-2-hydroxypropyl]-2,45 dihydro-[l,2,4]-triazole-3-thione of the formula: [B] (20) a phenylpyrrole derivative of the formula: wherein R3 and R4 each represent Cl, or together represent a radical of the 10 formula:-O-CF2-O-.
3
A method for controlling fungi, wherein the active compound combination as 15 defined in claim 1 or 2, is applied to the fungi, their habitat or both. CA 02944940 2016-10-12 ' 30725-11091 -604. Use of the active compound combination as defined in claim 1 or 2, for controlling fungi.
4
5. A process for preparing a fungicidal composition, comprising mixing the compound combination as defined in claim 1 or 2, with an extender, a surfactant or a mixture 5 thereof. OH (XXI)

Independent claims3

674 paragraphs in 74 sections, as filed

(57) Abrégé/Abstract:

The novel active compound combination comprising 2-[2-(1-chlorocyclopropy)-3-(2-chlorophenyl)-2-hydroxypropyl]-2,4-dihydro[1,2,4]- triazole-3-thione of the formula:

(see formula I) and the active compound [B] (20) a phenylpyrrole derivative of the formula:

(see formula XXI) wherein R3 and R4 each represent Cl, or together represent a radical of the formula: -O-CF2-O, has very good fungicidal properties.

Canada http://opic.gc.ca · Ottawa-Hull K1A 0C9 · http://cipo.gc.ca

O PI c

CIPO

OPIC-CIPO 191

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ABSTRACT

The novel active compound combination comprising 2-[2-(lchlorocyclopropyl)-3-(2-chlorophenyl)-2-hydroxypropyl]-2,4-dihydro-[l,2,4]-triazole-3thione of the formula:

and the active compound [B] (20) a phenylpyrrole derivative of the formula:

-R3

R4 CN (xxi) wherein R3 and R4 each represent Cl, or together represent a radical of the formula: -O-CF2-O, has very good fungicidal properties.

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Fungicidal active compound combinations

This application is a divisional application of copending application 2,905,473, filed

September 24, 2015, which is a divisional application of application 2,846,948, filed

March 20, 2014, issued to patent June 21,2016, which is a divisional application of application 2,800,471, filed December 21,2012, issued to patent May 31,2016, which is a divisional application of application 2,721,222, filed November 12, 2010, issued to Patent October 08, 2013, which is a divisional application of application 2,600,538, filed September 19, 2007, issued to patent February 15,2011, which is a divisional application of application 2,286,772, filed April 6, 1998, issued to patent June 17, 2008.

The present invention relates to novel active compound combinations which consist of the known 2-[2-(l-chlorocyclopropyl)-3-(2-chlorophenyl)-2-hydroxypropyl]-2,4-dihydro-[l,2,4]-triazole-3thione and further known fungicidally active compounds, and which are highly suitable for controlling phytopathogenic fungi.

It is already known that 2-[2-(l-chlorocyclopropyl)-3-(2-chlorophenyl)-2-hydroxy-propyl]-2,4dihydro-[l,2,4]-triazole-3-thione has fungicidal properties (cf. WO 96-16 048). The activity of this compound is good; however, at low application rates it is in some cases not satisfactory.

Furthermore, it is already known that a large number of triazole derivatives, aniline derivatives, dicarboximides and other heterocycles can be employed for controlling fungi (cf. EP-A 0 040 345, DE-A 2 201 063, DE-A 2 324 0 10, Pesticide Manual, 9th Edition (1991), pages 249 and 827, USA 3 903 090 and EP-A 0 206 999). Likewise, the activity of these compounds is not always satisfactory at low application rates.

Finally, it is also known that l-[(6-chloro-3-pyridinyl)-methyl]-N-nitro-2-imidazolidineimine can be used for controlling animal pests such as insects (cf. Pesticide Manual, 9th Edition (1991), page 491). However, fungicidal properties have not hitherto been described for this compound.

It has now been found that the novel active compound combinations comprising

2-[2-( 1 -chlorocyclopropyl)-3-(2-chlorophenyl)-2-hydroxypropyl]-2,4-dihydro-[ 1,2,4]-triazo le-3 thione of the formula

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-2OH όCH2—Ο-Cl

CH, (I) iY

-NH and ( 1 ) a triazole derivative of the formula

X—7 9—0-ÇH—Y—C(CH3)3 ΐ 1 m

-N in which

X represents chlorine or phenyl and

Y represents —CII o or

-CHI

OH and/or (2) the triazole derivative of the formula

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Cl \

OH

CH2-CHj—C 0^3)3

1h,

N

II 1' u-N (III) (tebuconazole) and/or (3) an aniline derivative of the formula

SO—N(CH3)2 in which

Rl represents hydrogen or methyl, and/or (4) N-[ 1 -(4-chloro-phenyl)-ethyl]-2,2-dichlor0- l-ethyl-3 -methylcyclopropane-carboxamide of the formula

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

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-4 S

II

CH, s

-Zn—S—C—NH—CH—CH—NH—C—S(propineb) (VI) and/or (6) at least one thiocarbamate of the formula

(VII)

Me = Zn or Mn or a mixture ofZn and Mn and/or (7) the aniline derivative of the formula 15

and/or (8) the compound of the formula

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O ÇHiCH^ ” I // w (CH,),CH—O—C—NH-CH—C-NH—CH-7' χχ

CH,

II o

CH, and/or (9) the benzothïadiazole derivative of the formula

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

(XI)

C3H7-n (spiroxamine) and/or ( 11 ) the compound of the formula

and/or

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-6(12) the compound of the formula

and/or (13) the compound of the formula

and/or ( 14) the dicarboximide of the formula

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

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in which

R2 represents methyl or cyclopropyl, and/or ( 16) the phenyl derivative of the formula

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

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

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-δ-

ε-cci3 (folpet) (XIX) and/or ( 19) the phosphorus compound of the formula

H,C,O a 5 2 \ //

P / \

Η O

Al (XX) (fosetyl-AI) and/or (20) a phenylpyrrole derivative of the formula

R3 and R4 each represent chlorine or together represent a radical of the 15 formula -O-CF2-O-, and/or (21) the l-[(6-chloro-3-pyridinyl)-methyl]-N-nitro-2-imidazolidineimine of the formula

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(XXII) (imidacloprid) and/or (22) the phenylurea derivative of the formula

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

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

R—NH—(CH,);

in which

-N——(CH,)

2'8 x (2 + m) CHjCOOH

-N—H (XXV)

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- 10m and

R5 represents integers from 0 to 5 represents hydrogen (17 to 23 %) or the radical of the formula

-c:=NH NH (77 to 83%).

have very good fungicidal properties.

Surprisingly, the fungicidal activity of the active compound combinations according to the invention is considerably higher than the sum of the activities of the individual active compounds. Thus, an unforeseeable, true synergistic effect is present, and not just an addition of activities.

The 2-[2-( l-chlorocyclopropyl)-3-(2-chIorophenyl)-2-hydroxypropyl]-2,4-dihydro[l,2,4]-triazole-3-thione of the formula (I) is known (cf. WO 96-16 048). The compound can be present in the „thiono„ form of the formula

or in the tautomeric „mercapto„ form of the formula

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-11Cl OH

(la).

For simplicity’s sake, only the „ thiono,, form is given in each case.

The formula (II) includes the compounds l-(4-chloro-phenoxy)-3,3-dimethyl-l-(l,2,4-triazol-l-yl)-butane-2-one of the formula

—CCCH^ (Ha) (triadimefon) l-(4-chloro-phenoxy)-3,3-dimethyl-l-(l,2,4-triazol-l-yl)-butan-2-oI of the formula

OH

CI C 7—O-CH-CH—C(CH3)3

ίΓ N 11 11 (lib) (triadimenol) and l-(4-phenyl-phenoxy)-3,3-dimethyl-l-(l,2,4-triazol-l-yl)-butan-2-ol of the formula

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OH .

CH—-CH-C(CH3)3

N 'N (He) (bitertanol)

The formula (IV) includes the aniline derivatives of the formulae

CCljF \

so—N(CH3)2 and (IVa) (dichlofluanid)

S-CCI,F /

\

SO2—N(CH3)2 (IVb) (tolylfluanid)

It is evident from the formula for the active compound of the formula (V) that the compound has three asymmetrically substituted carbon atoms. The product may therefore be present as a mixture of various isomers, or else in the form of a single component. Particular preference is given to the compounds

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

(R)

CO — NH — CH ch3 (R)

Cl (Va) c2H5 (S)

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- 13 and

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

The formula (VII) includes the compounds (Vila) Me = Zn (zineb) (Vllb) Me = Mn (maneb) and (Vile) mixture of (Vila) and (VHb) (mancozeb).

The formula (XVI) includes the compounds (XVIa) and · (XVIb)

R2 = CH3 (pyrimethanil)

-<]

R2 = (cyprodinyl)

The formula (XXI) includes the compounds

4-(2,3-dichlorophenyl)-pyrrole-3-earbonitrile of the formula

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- 14 or

N

Cl

CN (XXla) (fenpiclonil) and

4-(2,2-di luoro-l,3-benzodioxol-7-yl)-lH-pyrrole-3-carbonitrile of the formula

(XXIb) (fludioxonil)

The guanidine derivative of the formula (XXV) is a mixture of substances of the common name guazatine.

The components which are present in the active compound combinations according to the invention in addition to the active compound of the formula (I) are also known. Specifically, the active, compounds are described in the following publications:

(1) Compounds of the formula (II) . DE-A2 201 063

DE-A2 324 010 (2) Compound of the formula (III)

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

Pesticide Manual, 9th Edition (1991), pages 249 and 827 (4) Compound of the formula (V) and individual isomers thereof

EP-A 0 34 1 475

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-15(5) Compound of the formula (VI)

Pesticide Manual, 9th Edition (1991), page 726 (6) Compounds of the formula (VII)

Pesticide Manual, 9th Edition (1991), pages 529, 531 and 866 (7) Compound of the formula (VIII)

EP-A 0 339 418 (8) Compound of the formula (IX)

EP-A 0 472 996 (9) Compound of the formula (X)

EP-A 0 313 512 (10) Compound of the formula (XI)

EP-A 0 281 842 ( 11 ) Compound of the formula (XII)

EP-A 0 382 375 ( 12) Compound of the formula (ΧΙΠ)

EP-AO 515 901 ( 13) Compound of the formula (XIV)

EP-A 196 02 095 (14) Compound of the formula (XV)

US-A 3 903 090

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<td> (15></td><td> Compounds of the formula (XVI) EP-A 0 270 111 EP-A 0 310 550</td>

<td> 5 (16)</td><td> Compound of the formula (XVII) Pesticide Manual, 9th Edition (1991), page 159</td>

<td> (17)</td><td> Compound of the formula (XVIII) EP-A 0 219 756</td>

<td> (18)</td><td> Compound of the formula (XIX) Pesticide Manual, 9th Edition ( 1991), page 431</td>

<td> (19) 15</td><td> Compound of the formula (XX) Pesticide Manual, 9th Edition (1991), page 443</td>

<td> (20)</td><td> Compounds of the formula (XXI) EP-A 0 236 272 EP-A 0 206 999</td>

<td> (21)</td><td> Compound of the formula (XXII) Pesticide Manual, 9th Edition (1991), page 491</td>

<td> (22) 25</td><td> Compound of the formula (XXIII) DE-A2 732 257</td>

(23) Compound of the formula (XXIV)

EP-A 0 600 629 (24) Substance of the formula (XXV)

Pesticide Manual, 9th Edition (1991), page 461

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-17In addition to the active compound of the formula (I), the active compound combinations according to the invention comprise at least one active compound of the compounds of groups (I) to (24). Additionally, they may comprise further fungicidally active components.

The synergistic effect is particularly pronounced when the active compounds in the active compound combinations according to the invention are present in certain weight ratios. However, the weight ratios of the active compounds in thé active compound combinations can be varied within a relatively wide range. In general,

0.1 to 20 parts by weight, preferably 0.2 to 10 parts by weight, of active compound of group (1),

0.1 to 20 parts by weight, preferably 0.2 to 10 parts by weight, of active compound of 15 group (2),

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

0.1 to 10 parts by weight, preferably 0.2 to 5 parts by weight, of active compound of group (4), to 50 parts by weight, preferably 5 to 20 parts by weight, of active compound of group (5), to 50 parts by weight, preferably 2 to 20 parts by weight, of active compound of group (6),

0.1 to 50 parts by weight, preferably 1 to 30 parts by weight, of active compound of 30 group (7),

0.2 to 50 parts by weight, preferably 1 to 20 parts by weight, of active compound of group (8),

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- 180.02 to 50 parts by weight, preferably 0.2 to 10 parts by weight, of active compound of group (9),

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

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

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

0.1 to 50 parts by weight, preferably 0.2 to 20 parts by weight, of active compound of 15 group (13),

0.1 to 50 parts by weight, preferably 1 to 30 parts by weight, of active compound of group (14),

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

Ο. I to 50 parts by weight, preferably 2 to 20 parts by weight, of active compound of group (16), to 20 parts by weight, preferably 2 to 10 parts by weight, of active compound of group ( 17), to 50 parts by weight, preferably 2 to 20 parts by weight, of active compound of 30 group (18), to 50 parts by weight, preferably 2 to 20 parts by weight, of active compound of group (19),

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- 190.1 to 10 parts by weight, preferably 0.2 to 5 parts by weight, of active compound of group (20),

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

0.1 to 10 parts by weight, preferably 0.2 to 5 parts by weight, of active compound of group (22),

0.1 to 10 parts by weight, preferably 0.2 to 5 parts by weight, of active compound of group (23), and/or

0.1 to 10 parts by weight, preferably 0.2 to 5 parts by weight, of active compound of group (24) are present per part by weight of active compound of the formula (I).

The active compound combinations according to the invention have very good fungicidal properties and can be employed for controlling phytopathogenic fùngi, such as Plasmodiophoromycetes, Oomycetes, Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes, Deuteromycetes, etc.

25

The active compound combinations according to the invention are particularly suitable for controlling cereal diseases, such as Erysiphe, Puccinia and Fusarium, and for controlling diseases encountered in viticulture, such as Uncinula, Piasmopara and Botrytis, and furthermore in dicotylendonous crops for controlling powdery and downy mildew fungi and causative organisms of leaf spot.

The fact that the active compound combinations are well tolerated by plants at the concentrations required for controlling plant diseases permits the treatment of aboveCA 02944940 2016-10-12 '30725-11091

- 20 ground parts of plants, of propagation stock and seeds, and of the soil. The active compound combinations according to the invention can be employed for foliar application or else as seed dressings.

The active compound combinations according to the invention can be converted to the customary formulations, such as solutions, emulsions, suspensions, powders, foams, pastes, granules, aerosols and microencapsulations in polymeric substances and in coating compositions for seeds, and ULV formulations.

These formulations are produced in a known manner, for example by mixing the active compounds or active compound combinations with extenders, that is· liquid solvents, liquefied gases under pressure, and/or solid carriers, optionally with the use of surfactants, that is emulsifiers and/or dispersants, and/or foam formers. If the extender used is water, it is also possible to use, for example, organic solvents as auxiliary solvents. Essentially, suitable liquid solvents include: aromatics such as xylene, toluene or alkylnaphthalenes, chlorinated aromatics or chlorinated aliphatic hydrocarbons such as chlorobenzenes, chloroethylenes or methylene chloride, aliphatic hydrocarbons such as cyclohexane or paraffins, for example petroleum fractions, alcohols such as butanol or glycol and their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as dimethylformamide and dimethyl sulphoxide, or else water. Liquefied gaseous extenders or carriers are to be understood as meaning liquids which are gaseous at ambient temperature and under atmospheric pressure, for example aerosol propellants such as butane, propane, . nitrogen and carbon dioxide. Suitable solid carriers are: for example ground natural minerals such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, and ground synthetic minerals such as finely divided silica, alumina and silicates. Suitable solid carriers for granules are: for example crushed and fractionated natural rocks such as calcite, marble, pumice, sepiolite and dolomite, or else synthetic granules of inorganic and ?>0 organic meals, and granules of organic material such as sawdust, coconut shells, maize cobs and tobacco stalks. Suitable emulsifiers and/or foam formers are: for example nonionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglyco! ethers, alkylCA 02944940 2016-10-12 '30725-11091

-21 sulphonates, alkyl sulphates, arylsulphonates, or else protein hydrolysates. Suitable dispersants are: for example lignin-sulphite waste liquors and methylcellulose.

Tackifiers such as carboxymethylcellulose and natural and synthetic polymers in the form of powders, granules or latices, such as gum arable, polyvinyl alcohol and polyvinyl acetate, or else natural phospholipids such as cephalins and lecithins and synthetic phospholipids can be used in the formulations. Other additives can be mineral and vegetable oils.

It is possible to use colorants such as inorganic pigments, for example iron oxide, titanium oxide and prussian blue, and organic dyestuffs such as alizarin dyestuffs, azo dyestuffs and metal phthalocyanine dyestuffs, and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.

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

In the formulations, the active compound combinations according to the invention can be present as a mixture with other known active compounds such as fungicides, insecticides, acaricides and herbicides, and as mixtures with fertilizers or plant growth regulators.

The active compound combinations can be used as such, in the form of their formulations or as the use forms prepared therefrom, such as ready-to-use solutions, emulsifiable concentrates, emulsions, suspensions, wettable powders, soluble powders and granules. They are used in the customary manner, for example by watering, spraying, atomizing, scattering, spreading, and as a powder for dry seed treatment, a solution for seed treatment, a water-soluble powder for seed treatment, a watersoluble powder for slurry treatment, or by encrusting.

When using the active compound combinations according to the invention, the application rates can be varied within a relatively wide range, depending on die kind of application, in the treatment of parts of plants, the application rates of the active

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-22compound combination are generally between 0.1 and 10,000 g/ha, preferably between 10 and 1000 g/ha. In the treatment of seeds, the application rates of the active compound combination are generally between 0.001 and 50 g per kilogram of seed, preferably between 0.01 and 10 g per kilogram of seed. In the treatment of the soil, the application rates of the active compound combination are generally between 0.1 and 10,000 g/ha, preferably between I and 5000 g/ha.

The good fungicidal activity of the active compound combinations according to the invention is evident from the examples below. While the individual active compounds exhibit weaknesses with regard to the fungicidal activity, the combinations have an activity which exceeds a simple addition of activities.

A synergistic effect of fungicides is always present when the fungicidal activity of the active compound combinations exceeds the total of the activities of the active compounds when applied individually.

The expected activity for a given combination of two active compounds can be calculated as follows (cf. Colby, S.R., Calculating Synergistic and Antagonistic Responses of Herbicide Combinations, Weeds 15. (1967), 20-22):

If

X ' is the efficacy when applying active compound A at an application rate of m g/ha,

Y is the efficacy when applying active compound B at an application rate of n g/ha and

E is the efficacy when applying the active compounds A and B at an application 30 rate of m and n g/ha.

then

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-23 γ. γ

Ε = X + V-^-4

100

The efficacy is calculated in %. 0% is an efficacy which corresponds to that of the control, whereas an efficacy of 100% means that no infection is observed.

If the actual fungicidal activity exceeds the calculated value, then the activity of the combination is superadditive, i.e. a synergistic effect exists. In this case, the efficacy which was actually observed must be greater than the value for the expected efficacy (E) calculated from the abovementioned formula.

10

The examples that follow illustrate the invention.

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-24Example 1

Sphaerotheca test (cucumber) / protective

Solvent: 47 parts by weight of acetone

Emulsifier: 3 parts by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weight of active compound or active compound combination is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration, or a commercial formulation of active compound or active compound combination is diluted with water to the desired concentration.

To test for protective activity, young plants are sprayed with the active compound preparation at the stated application rate. After the spray coating has dried on, the plants are inoculated with an aqueous spore suspension of Sphaerotheca fuliginea. The plants are then placed in a greenhouse at about 23°C and a relative atmospheric humidity of about 70%.

Evaluation is carried out 10 days after the inoculation. 0% means an efficacy which corresponds to that of the control, whereas an efficacy of 100% means that no infection is observed.

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

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- 25 Table 1

Sphaerotheca test (cucumber) / protective

<td> Active compound</td><td> Active compound application rate in g/ha</td><td> Efficacy in %</td>

<td> Known: Cl OH ft S—CH,-C//- -Cl \=A | ÇH2 m'N'O ® U-L</td><td> 2.5 0.5</td><td> 21 0</td>

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-31 Table L (continued)

Sphaerotheca test (cucumber) / protective

<td> Active compound</td><td> Active compound application rate in g/ha</td><td colspan="2"> Efficacy in %</td>

<td> a</td><td> y</td><td> found 63</td><td> calc.*) 21</td>

<td> (XVIII)]</td><td> 12.5 j</td><td></td><td></td>

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- 32T able 1 (continued)

Sphaerotheca test (cucumber) / protective

<td colspan="2"> Active compound</td><td> Active compound application rate in g/ha</td><td colspan="2"> Efficacy in %</td>

<td> ϋ</td><td></td><td> 25~l + \</td><td> found 50</td><td> calc.*) 21</td>

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- jj Table 1 (continued)

Sphaerotheca test (cucumber) / protective

<td> Active compound</td><td> Active compound application rate in g/ha</td><td colspan="2"> Efficacy in %</td>

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-34Table 1 (continued)

Sphaerotheca test (cucumber) / protective

<td> Active compound</td><td> Active compound application rate in g/ha</td><td> Efficacy in °/o ]</td>

<td> - ]</td><td> 2751</td><td> found calc.*)</td>

found = calc. = efficacy found efficacy calculated using the Colby formula

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-35Exatnple 2

Venturia test (apple) / protective

Solvent: 47 parts by weight of acetone

Emulsifier: 3 parts by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weight of active compound or active compound combination is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration, or a commercial formulation of active compound or active compound combination is diluted with water to the desired concentration.

To test for protective activity, young plants are sprayed with the active compound preparation at the stated application rate. After the spray coating has dried on, the plants are inoculated with an aqueous konidia suspension of the causative organism of apple scab Venturia inaequalis and then remain in an incubation cabin at about 20°C and 100% relative atmospheric humidity for one day.

The plants are then placed in a greenhouse at about 21 °C and a relative atmospheric humidity of about 90%.

Evaluation is carried out 12 days lifter the inoculation. 0% means an efficacy which corresponds to that of the control, whereas an efficacy of 100% means that no infection is observed.

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

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-36Table 2

caic. = efficacy calculated using the Colby formula

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- 37Example 3

Erysiphe test (barley) ! curative

Solvent: 10 parts by weight of N-methyl-pyrrolido ne

Emulsifier: 0.6 parts by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weight of active compound or active compound combination is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration, or a commercial formulation of active compound or active compound combination is diluted with water to the desired concentration.

To test for curative activity, young plants are dusted with spores of Erysiphe graminis

f.sp. hordei. 48 hours after the inoculation, the plants are sprayed with the active compound preparation at the stated application rate.

The plants are placed in a greenhouse at a temperature of about 20°C and a relative atmospheric humidity of about 80% to promote the development of mildew pustules.

Evaluation is carried out 7 days after the inoculation. 0% means an efficacy which corresponds to that of the control, whereas an efficacy of 100% means that no infection is observed.

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

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-38Table 3

Erysiphe test (barley) / curative

<td> Active compound</td><td> Active compound application rate in g/ha</td><td> Efficacy in %</td>

<td> Known: Cl OH <Z —CH2 C — C| CH, ] 2 (D u-NH</td><td> 25</td><td> 81</td>

<td> According to the invention: A (XIV)J (1:3)</td><td> 6.251 + \ 18.75 ί</td><td> 100</td>

CA 02944940 2016-10-12 '30725-11091

-39Example 4

Erysiphe test (barley) / protective

Solvent: 10 parts by weight of N-methyl-pyrrolidone

Emulsifier: 0.6 parts by weight of alkylaryl polyglycot ether

To produce a suitable preparation of active compound, 1 part by weight of active compound or active compound combination is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration, or a commercial formulation of active compound or active compound combination is diluted with water to the desired concentration.

To test for protective activity, young plants are sprayed with the active compound preparation at the stated application rate.

After the spray coating has dried on, the plants are dusted with spores of Erysiphe graminis f.sp. hordei.

The plants are placed in a greenhouse at a temperature of about 20°C and a relative atmospheric humidity of about 80% to promote the development of mildew pustules.

Evaluation is carried out 7 days after the inoculation. 0% means an efficacy, which corresponds to that of the control, whereas an efficacy of 100% means that no infection is observed.

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

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-40Table 4

Erysiphe test (barley) I protective

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- 41 Example 5

Erysiphe test (wheat) / curative

Solvent: 10 parts by weight of N-methyl-pyrrolidone

Emulsifier: 0.6 parts by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weight of active compound or active compound combination is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration, or a commercial formulation of active compound or active compound combination is diluted with water to the desired concentration.

To test for curative activity, young plants are dusted with spores of Erysiphe graminis

f.sp. tritici. 48 hours after the inoculation, the plants are sprayed with the active compound preparation at the stated application rate.

The plants are then placed in a greenhouse at a temperature of about 20°C and a relative atmospheric humidity of about 80% to promote the development of mildew pustules.

Evaluation is carried out 7 days after the inoculation. 0% means an efficacy which corresponds to that of the control, whereas an efficacy of 100% means that no infection is observed.

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

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-42Tnble 5

Erysiphe test (wheat) / curative

<td colspan="3"> Active compound</td><td> Active compound application rate in g/ha</td><td> . Efficacy in %</td>

<td> Known:</td><td></td><td></td><td></td><td></td>

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-43 Table 5 (continued)

Erysiphe test (wheat) / curative

<td> Active compound</td><td> Active compound application rate in g/ha</td><td> Efficacy in %</td>

<td> According to the invention:</td><td> 12.3-I A</td><td> 100</td>

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-44 Table 5 (continued)

Erysiphe test (wheat) / curative

<td colspan="2"> Active compound</td><td> Active compound application rate in g/ha</td><td> Efficacy in % !</td>

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-45 Table 5 (continued)

Erysiphe test (wheat) / curative

<td colspan="3"> Active compound</td><td rowspan="2"> Active compound application rate in g/ha 6.25Ί + \ 6.25 j</td><td rowspan="2"> Efficacy in % 1 63</td>

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-46 Table 5 (continued)

Erysiphe test (wheat) / curative

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-47Example 6

Erysiphe test (wheat) / protective

Solvent: 10 parts by weight of N-methyl-pyrrolidone

Emulsifier: 0.6 parts by weight of alkylaiyl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weight of active compound or active compound combination is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration, or a commercial formulation of active compound or active compound combination is diluted with water to the desired concentration.

To test for protective activity, young plants are sprayed with the active compound preparation at the stated application rate.

After the spray coating has dried on, the plants are dusted with spores of Erysiphe graminis f.sp. tritici.

The plants are then placed in a greenhouse at a temperature of about 20°C and a relative atmospheric humidity of about 80% to promote the development of mildew pustules.

Evaluation is carried out 7 days after the inoculation. 0% means an efficacy which corresponds to that of the control, whereas an efficacy of 100% means that no infection is observed.

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

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-48 Table 6

Erysiphe test (wheat) / protective

<td> Active compound . .</td><td> Active compound application rate in g/ha</td><td> Efficacy in % 8</td>

<td> Known: ci °h — ch2 C - -CI cn* (l) 7rs u-NH</td><td> 6.25</td><td> 57</td>

<td> According to the invention: / onj (1:1)</td><td> 3.125] 7 3.125</td><td> 79</td>

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-49 Example 7

Leptosphaeria nodorum test (wheat) I protective

Solvent: 10 parts by weight of N-methyl-pyrrolidone

Emulsifier: 0.6 parts by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weight of active compound or active compound combination is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration, or a commercial formulation of active compound or active compound combination is diluted with water to the desired concentration.

To test for protective activity, young plants are sprayed with the active compound preparation at the stated application rate.

After the spray coating has dried on, the plants are sprayed with a spore suspension of Leptosphaeria nodorum. The plants remain in an incubation cabin at 20°C and 100% relative atmospheric humidity for 48 hours.

The plants are then placed in a greenhouse at a temperature of about 15°C and a relative atmospheric humidity of about 80%.

Evaluation is carried out 10 days after the inoculation. 0% means an efficacy which corresponds to that of the control, whereas an efficacy of 100% means that no infection is observed.

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

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- 50Tabie 7

Leptosphaeria nodorum test (wheat) / protective

<td colspan="3"> Active compound</td><td> Active compound application rate in g/ha</td><td> Efficacy in % |</td>

<td> Known:</td><td></td><td></td><td></td><td></td>

<td colspan="2"> According to the invention:</td><td></td><td></td><td></td>

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- 51 Example 8

Puccinia test (wheat) / protective

Solvent: 10 parts by weight of N-methyl-pyrrolidone

Emulsifier: 0.6 parts by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weight of active compound or active compound combination is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration, or a commercial formulation of active compound or active compound combination is diluted with water to the desired concentration.

To test for protective activity, young plants are inoculated with a spore suspension of

Puccinia recondita in a 0.1% strength aqueous agar solution. After the spray coating had dried on, the plants are sprayed with the active compound preparation at the stated application rate.

The plants remain in an incubation cabin at 20°C and 100% relative atmospheric humidity for 24 hours.

The plants are then placed in a greenhouse at a temperature of about 20°C and a relative atmospheric humidity of about 80% to promote the development of rust pustules.

Evaluation is carried out 10 days after the inoculation. 0% means an efficacy which corresponds to that of the control, whereas an efficacy of 100% means that no infection is observed.

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

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- 52 Table 8

Puccinia test (wheat) / protective

<td colspan="2"> I Active compound</td><td> Active compound application rate in g/ha</td><td> Efficacy in %</td>

<td> Known:</td><td></td><td></td><td></td>

<td> According to the invention:</td><td></td><td></td><td></td>

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- 53 Example 9

Fusarium culmorum test (wheat) / seed treatment

The active compounds are applied as a dry seed dressing. This is prepared by extending the respective active compound or the active compound combination with ground minerals to give a finely pulverulent mixture which ensures uniform distribution on the seed surface.

To dress the seed, the infected seed together with the seed dressing is shaken for 3 minutes in a sealed glass flask.

x 100 corns of wheat are sown at a depth of 1 cm in standard soil and cultivated in a greenhouse at a temperature of about 18°C and a relative atmospheric humidity of about 95% in seed trays which receive a light regimen of 15 hours per day.

About 3 weeks after sowing, the plants are evaluated for symptoms. 0% means an efficacy which corresponds to that of the control, whereas an efficacy of 100% means that no infection is observed.

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

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- 54Table 9

Fusarium culmorum test (wheat) / seed treatment

<td colspan="2"> Active compound</td><td> Active compound application rate in g/ha</td><td> Efficacy in %</td>

<td> Known:</td><td></td><td></td><td></td>

<td colspan="2"> According to the invention:</td><td></td><td></td>

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- 55 Example 10

Fusarium nivale test (triticale) I seed treatment

The active compounds are applied as a dry seed dressing. This is prepared by extending the respective active compound or the active compound combination with ground minerals to give a finely pulverulent mixture which ensures uniform distribution on the seed surface.

To dress the seed, the infected seed together with the seed dressing is shaken for 3 minutes in a sealed glass flask.

x 100 corns of wheat are sown at a depth of 1 cm in standard soil and cultivated in a greenhouse at a temperature of about 10°C and a relative atmospheric humidity of about 95% in seed trays which receive a light regimen of 15 hours per day.

About 3 weeks after sowing, the plants are evaluated for symptoms. 0% means an efficacy which corresponds to that of the control, whereas an efficacy of 100% means that no infection is observed.

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

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-56Table 10

Fusarium nivale test (triticale) / seed treatment

<td> Active compound</td><td> Active compound application rate in g/ha</td><td> Efficacy in %</td>

<td> Known: ci °h —ch,-C -Cj CH, 1 2 (ο 11-NH</td><td> 75 25</td><td> 14 0</td>

<td> According to the invention: Λ (χι\ο| (1:1)</td><td> 37+1 + X 37.5 J</td><td> 99</td>

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-57Example 11

Rhizoctonia solani test (cotton) / seed treatment

The active compounds are applied as a dry seed dressing. This is prepared by extending the respective active compound or the active compound combination with ground minerals to give a finely pulverulent mixture which ensures uniform distribution on the seed surface.

To dress the seed, the infected seed together with the seed dressing is shaken for 3 minutes in a sealed glass flask.

x 50 corns of seed are sown at a depth of 2 cm in standard soil infected with Rhizoctonia solani, and the seeds are cultivated in a greenhouse at a temperature of about 22°C in seed trays which receive a light regimen of 15 hours per day.

Evaluation is carried out after 8 days. 0% means an efficacy which corresponds to that of the control, whereas an efficacy of 100% means that no infection is observed.

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

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-58Table 11

Rhizoctonia solan! test (cotton) / seed treatment

<td> Active compound</td><td></td><td></td><td></td><td> Active compound application rate in g/ha</td><td> Efficacy in % j</td>

<td> Known:</td><td></td><td></td><td></td><td></td><td></td>

<td colspan="2"> Accordine to the invention:</td><td></td><td></td><td></td><td></td>

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Contents74

38 sheets

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84 members in 31 offices

This recordMember, by publication datePriority claim21 more offices are in the list below

Priority claims9

Priority claims
Document	Office	Kind	Date
197162576	Germany	–	1997-04-18
19716257	Germany	A	1997-04-18
19716257	Germany	A	1997-04-18
2905473	Canada	A	1998-04-06
2905473	Canada	A	1998-04-06
197162576	–	–	–
2905473	–	–	–
CA19982905473	–	–	–
DE1997116257	–	–	–

Members84

Family members, oldest first
Document	Office	Kind
DE19716257A1	Germany	A1	1998-10-22
ZA983236B	South Africa	B	1998-10-22
CA2286772A1	Canada	A1	1998-10-29
CA2600538A1	Canada	A1	1998-10-29
CA2721222A1	Canada	A1	1998-10-29
CA2800471A1	Canada	A1	1998-10-29
CA2846948A1	Canada	A1	1998-10-29
CA2905473A1	Canada	A1	1998-10-29
CA2944940A1	Canada	A1	1998-10-29
WO9847367A1	World Intellectual Property Organization (WIPO)	A1	1998-10-29
AU7522098A	Australia	A	1998-11-13
ID22820A	Indonesia	A	1999-12-09
TR199902400T2	Türkiye	T2	2000-01-21
EP0975219A1	European Patent Office (EPO)	A1	2000-02-02
CZ369699A3	Czechia	A3	2000-02-16
EA199900916A1	Eurasian Patent Organization (EAPO)	A1	2000-04-24
CN1252690A	China	A	2000-05-10
SK143599A3	Slovakia	A3	2000-06-12
EE9900500A	Estonia	A	2000-06-15
PL336226A1	Poland	A1	2000-06-19
BR9809100A	Brazil	A	2000-08-01
HU0001682A2	Hungary	A2	2000-09-28
HUP0001682A2	Hungary	A2	2000-09-28
NZ500367A	New Zealand	A	2000-09-29
AU727186B2	Australia	B2	2000-12-07
HK1026822A1	Hong Kong, China	A1	2000-12-29
KR20010006063A	Republic of Korea	A	2001-01-15
IL131900D0	Israel	D0	2001-03-19
US6306850B1	United States of America	B1	2001-10-23
JP2001520665A	Japan	A	2001-10-30
HU0001682A3	Hungary	A3	2002-02-28
HUP0001682A3	Hungary	A3	2002-02-28
EP0975219B1	European Patent Office (EPO)	B1	2002-03-13
AT214230T	Austria	T	2002-03-15
ATE214230T1	Austria	T1	2002-03-15
EE03657B1	Estonia	B1	2002-04-15
DE59803337D1	Germany	D1	2002-04-18
EA002598B1	Eurasian Patent Organization (EAPO)	B1	2002-06-27
DK0975219T3	Denmark	T3	2002-07-01
ES2172143T3	Spain	T3	2002-09-16
PT975219E	Portugal	E	2002-09-30
TW505504B	Taiwan Province of China	B	2002-10-11
SI0975219T1	Slovenia	T1	2002-10-31
US2002173529A1	United States of America	A1	2002-11-21
UA55451C2	Ukraine	C2	2003-04-15
CN1109499C	China	C	2003-05-28
IL131900A	Israel	A	2004-07-25
SK284214B6	Slovakia	B6	2004-11-03
KR100525469B1	Republic of Korea	B1	2005-11-02
NL350024I1	Netherlands (Kingdom of the)	I1	2006-03-01
NL350024I2	Netherlands (Kingdom of the)	I2	2006-04-03
CZ296701B6	Czechia	B6	2006-05-17
PL191483B1	Poland	B1	2006-05-31
FR06C0041I1	France	I1	2007-01-12
NL350031I1	Netherlands (Kingdom of the)	I1	2007-02-01
NL350031I2	Netherlands (Kingdom of the)	I2	2007-03-01
JP4094067B2	Japan	B2	2008-06-04
CA2286772C	Canada	C	2008-06-17
DE122008000040I2	Germany	I2	2008-11-06
FR06C0041I2	France	I2	2009-10-30
US2009306109A1	United States of America	A1	2009-12-10
HU227139B1	Hungary	B1	2010-08-30
BR9809100B1	Brazil	B1	2010-11-16
FR10C0046I1	France	I1	2010-12-24
FR10C0051I1	France	I1	2011-01-14
CA2600538C	Canada	C	2011-02-15
FR10C0046I2	France	I2	2012-10-26
FR10C0051I2	France	I2	2012-10-26
US2013190371A1	United States of America	A1	2013-07-25
CA2721222C	Canada	C	2013-10-08
US2013296389A1	United States of America	A1	2013-11-07
US8637534B2	United States of America	B2	2014-01-28
US2014066407A1	United States of America	A1	2014-03-06
US8846738B2	United States of America	B2	2014-09-30
US2014364469A1	United States of America	A1	2014-12-11
FR15C0057I1	France	I1	2015-09-25
US9253982B2	United States of America	B2	2016-02-09
FR15C0057I2	France	I2	2016-02-12
US2016106105A1	United States of America	A1	2016-04-21
CA2800471C	Canada	C	2016-05-31
CA2846948C	Canada	C	2016-06-21
US9445601B2	United States of America	B2	2016-09-20
CA2944940CThis record	Canada	C	2017-02-28
CA2905473C	Canada	C	2017-05-30

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	Event	Code
2018-06-10	ExpiryMKEX	MKEX
2016-11-07	Examination requestEEER	EEER
2016-10-27	Examination requestEEER	EEER

Numbers

Publication: 2944940
Publication, DOCDB: 2944940
Publication, EPODOC: CA2944940
Application: 2944940
Application, DOCDB: 2944940
Application, EPODOC: CA19982944940

Titles2

English: FUNGICIDAL ACTIVE COMPOUND COMBINATIONS
French: COMBINAISONS DE SUBSTANCES ACTIVES FONGICIDES

Classification

CPC, 24: A01N43/653
A01N57/12
A01N37/18
A01N37/20
A01N37/22
A01N37/24
A01N37/34
A01N37/38
A01N37/50
A01N43/30
A01N43/36
A01N43/38
A01N43/54
A01N43/82
A01N43/84
A01N43/88
A01N47/04
A01N47/10
A01N47/12
A01N47/14
A01N47/32
A01N51/00
A01N53/00
A01N55/02
Filled: the office’s first classification
IPC, 50: A01N43 653
A01N43 36
A01P3 00
A01N
A01N37 18
A01N37 24
A01N37 26
A01N37 34
A01N37 50
A01N41 02
A01N41 06
A01N43 06
A01N43 30
A01N43 34
A01N43 48
A01N43 54
A01N43 64
A01N43 828
A01N43 84
A01N43 88
A01N47 04
A01N47 10
A01N47 12
A01N47 28
A01N47 30
A01N47 32
A01N47 44
A01N51 00
A01N53 12
A01N55 02
A01N57 10
A01N57 12
A61K31 535
C07C233 57
C07C233 64
C07C251 34
C07C255 51
C07C271 06
C07C279 04
C07C313 36
C07D207 34
C07D209 30
C07D239 28
C07D249 00
C07D265 28
C07D285 14
C07D317 06
C07D401 06
C07D413 12
C07F9 141

Abstract

Term

CIPO

OPIC-CIPO 191

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ABSTRACT

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-CHI

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OH

N

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-4 S

II

(VII)

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CH,

(XI)

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R—NH—(CH,);

-N——(CH,)

-N—H (XXV)

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OH

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S-CCI,F /

(R)

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N

EP-A 0 34 1 475

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US-A 3 903 090

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Priority claims9

Members84

Over the term

Events