PatentDe  


Dokumentenidentifikation EP1017280 23.09.2004
EP-Veröffentlichungsnummer 0001017280
Titel SAATGUTBEHANDLUNGS-FUNGIZID ZUR BEKÄMPFUNG VON PFLANZENKRANKHEITEN
Anmelder Uniroyal Chemical Co., Inc., Middlebury, Conn., US
Erfinder RIGGS, Lynn, Jenifer, Plano, US;
HAIRSTON, Gordon, William, Plano, US;
ARTHUR, Sue, Karen, Plano, US
Vertreter Spott & Weinmiller, 80336 München
DE-Aktenzeichen 69825766
Vertragsstaaten AT, DE, DK, ES, FI, FR, GB, IT, NL
Sprache des Dokument EN
EP-Anmeldetag 01.09.1998
EP-Aktenzeichen 989435185
WO-Anmeldetag 01.09.1998
PCT-Aktenzeichen PCT/US98/18221
WO-Veröffentlichungsnummer 0099013722
WO-Veröffentlichungsdatum 25.03.1999
EP-Offenlegungsdatum 12.07.2000
EP date of grant 18.08.2004
Veröffentlichungstag im Patentblatt 23.09.2004
IPC-Hauptklasse A01N 47/34

Beschreibung[en]
Field of the Invention

This invention relates to a method for controlling fungus diseases in plants by applying to the seed or tuber a fungicidally effective amount of a 2-alkoxyiminoacetamide compound such as cymoxanil, in admixture with one or more of an alkylene bis-dithiocarbamate complex salt such as mancozeb, and a thiophanate compound such as thiophanate-methyl. This invention also relates to a fungicidal composition comprising, in a fungicidally effective aggregate amount, a 2-alkoxyiminoacetamide compound, an alkylene bis-dithiocarbamate complex salt, and a thiophanate compound.

Background of the Invention

Late Blight is the devastating disease that affected the Irish potato crop over 150 years ago. Today, however, the Late Blight fungus, Phytophthora infestans, is much different that its ancestors. New strains of P. infestans have evolved that are fungicide resistant and which are more aggressive with respect to pathogenicity on the potato tuber. As a result, the disease can now be introduced into potato fields by means of infected seed tubers more efficiently than in the past.

It is the purpose of this invention to provide a novel method for combatting plant fungi, particularly phytopathogenic fungi such as Phytophthora infestans. It is a purpose to provide a novel fungicidal composition useful for combatting plant fungi, particularly phytophogenic fungi such as Phytophthora infestans. GB-A-1 470 740 discloses a fungicidal mixture comprising 1 to 10 parts by weight of

and from 1 to 1000 parts by weight of a fungicide selected from manganese ethylene-bisdithiocarbamate, admixed with inorganic zinc salts; co-ordination product of zinc ion and manganese ethylenebisdithiocarbamate (mancozeb); zinc ethylene bisdithiocarbamate; fixed copper; N-(trichloromethylthio)phthalimide (folpet); 2,4,5,6-tetrachloroisophthalonitrile (chlorothalonil); cis-N-[(1,1,2,2-tetrachloroethyl)thio]-4-cyclohexene-1,2-dicarboximide (captafol); and triphenyltin hydroxide.

DD-A-298 340 discloses compositions which preferably comprise a combination of carbendazim, fenarimol and cymoxanil, for controlling Fusarium dry-blight of potatoes.

Ann. Appl. Biol. (1987), 110, 53-63 describes a glasshouse test for the evaluation of the systemic activity of chemicals including cymoxanil, for the control of Plasmopara halstedii, the downy mildew pathogen of sunflower.

Plant Dis. (1989), 73(9), 751-3 describes a field control of potato late blight by fungicides selected from the group consisting of oxadixyl, metalaxyl, propamocarb, cymoxanil, and mancozeb and mixtures thereof.

Crop Prot. (1988), 7(3), 210-15 describes a test concerning the efficacy over time of cymoxanil mixtures in controlling late blight in potatoes incited by a phenylamide-resistant isolate of Phytophthora infestans.

Phytopathology (1988), 78(6), 636-40 describes cymoxanil mixtures with either mancozeb or with mancozeb and oxadixyl in controlling both metalaxyl-sensitive and -resistant Phytophthora infestans in potatoes.

US-A-5 007 953 discloses methods of using comminuted Alder bark as a stimulator of seed germination and growth media comprising comminuted Alder bark.

RO-A-80510 discloses a composition for fighting tuber and tuber-bulb rot comprising mancozeb combined with benomil, methyl thiophanate or thia-bendazole and tetracycline or chloramphenicol.

Summary of the Invention

This invention relates to a method for combatting plant fungi in a plant, which comprises applying to the seeds or tubers of the plant, a fungicidally effective amount of:

  • a) a 2-alkoxyiminoacetamide compound of the formula:
       wherein R is methyl or ethyl and R1 hydrogen, C1-C4 alkyl or allyl, preferably, C1-C4 alkyl, more preferably, methyl or ethyl;
  • b) an alkylene bis-dithiocarbamate complex salt of the formula:
       wherein R4 and R5 are each, independently, hydrogen or C1-C6 alkyl, preferably, hydrogen or C1-C4 alkyl, more preferably, hydrogen, methyl or ethyl; Q is Zn, Fe, or Cu, preferably, Zn; and the ratio of x to y is from about 3:1 to about 100:1, preferably, about 5:1 to about 20:1, more preferably, about 6:1 to about 10:1.

    and
  • C) a thiophanate compound of the formula:
       wherein R2 and R3 are each, independently, C1-C6 alkyl, preferably, C1-C4 alkyl, more preferably, methyl or ethyl.

This invention further relates to a fungicidal composition comprising:

  • a) a 2-alkoxyiminoacetamide compound of the formula:
       wherein R is methyl or ethyl and R1 hydrogen, C1-C4 alkyl or allyl, preferably, C1-C4 alkyl, more preferably, methyl or ethyl;
  • b) an alkylene bis-dithiocarbamate complex salt of the formula:
       wherein R4 and R5 are each, independently, hydrogen or C1-C6 alkyl, preferably, hydrogen or C1-C4 alkyl, more preferably, hydrogen, methyl or ethyl; Q is Zn, Fe, or Cu, preferably, Zn; and the ratio of x to y is from about 3:1 to about 100:1, preferably, about 5:1 to about 20:1, more preferably, about 6:1 to about 10:1; and
  • c) a thiophanate compound of the formula:
   wherein R2 and R3 are each, independently, C1-C6 alkyl, preferably, C1-C4 alkyl, more preferably, methyl or ethyl,

in an effective aggregate amount.

Description of the Invention

The 2-alkoxyiminoacetamide compounds, alkylene bis-dithiocarbamate complex salts, and thiophanate compounds useful in the method and composition of this invention, are known in the art, as are methods for their preparation. See, e.g., U. S. Patents Nos. 3,957,847; 3,379,610; and 5,571,443, respectively.

The method and composition of this invention are particularly suitable for use against Phytophthora infestans on or in potato plants and tubers.

The composition of this invention and the compounds useful in the method of this invention can be formulated in conventional ways. Examples of useful formulations include slurries, solid seed coatings, soaks, dusts on the surface of the seed or tuber, solutions, suspensions, emulsions, wettable powders, emulsifiable concentrates, and the like. The formulations, in general, comprise about 1% to 99% by weight of active ingredient. The formulations can additionally comprise additional additives such as surfactants, solid or liquid diluents, pigments, thickeners, and the like. The method of application of the formulations to the seeds or tubers can vary depending, e.g., on the compounds and/or the formulation used.

In general, the seed or tuber should be treated with about 50 to about 1200 ppm, preferably between about 300 to about 900 ppm, most preferably, about 700 ppm, per 45.36 kg (100 pounds) ("cwt") of seed or tuber, of the composition of this invention or of the compounds useful in the method of this invention.

This invention preferably relates to a method for combatting plant fungi in a plant, which comprises applying to the seeds or tubers of the plant, an effective amount of a fungicidal composition comprising a fungicidally effective amount of:

  • a) cymoxanil; or
  • b) cymoxanil in admixture with one or more of the group consisting of mancozeb and thiophanate-methyl.

This invention further preferably relates to a fungicidal composition comprising cymoxanil, mancozeb and thiophanate-methyl, in an effective aggregate amount.

Cymoxanil, mancozeb and thiophanate-methyl are all known compounds.

Cymoxanil (a foliar fungicide sold under the trademarks CURZATE and DPX-3217) is 2-cyano-N-[(ethylamino)carbonyl]-2-(methoxyimino)-acetamide.

Mancozeb (a fungicide sold under the trademarksMANZATE-200 and DITHANE M-45) is a mixture of [[1,2-ethanediylbis-(carbamodithioato)](2-)]manganese and [[1,2-ethanediylbis(carbamothioato)](2)-]zinc.

Thiophanate-methyl (a systemic fungicide sold under the trademarks TOPSIN M and NF-44) is dimethyl[1,2-phenylene-bis-(iminocarbono-thioyl)-bis-[carbamate].

In the method of this invention wherein cymoxanil, mancozeb and thiophanate-methyl are admixed, in general, satisfactory results can be obtained when the weight ratio of cymoxanil:mancozeb:thiophanate-methyl is from about 3:1:1 to about 1:16:6, preferably, about 1.5:1:1 to about 1:8:3.

Similarly, in the composition of this invention, in general, satisfactory results can be obtained when the weight ratio of cymoxanil:mancozeb:thiophanate-methyl is from about 3:1:1 to about 1:16:6, preferably, about 1.5:1:1 to about 1:8:3.

The formulations can comprise from 0 to about 20% of an agriculturally acceptable surfactant such as wetting and dispersing agents, e.g., the condensation product of formaldehyde with naphthalene sulphonate, an alkylarylsulphonate, a lignin sulphonate, a fatty sulphate, an ethoxylated alkylphenol and an ethoxylated fatty alcohol. The formulations can additionally comprise from about 10 to about 99% of an agriculturally acceptable solid or liquid diluent, including carriers, such as talc, zeolites, Alder bark, kaolin, diatomaceous earth, mineral oil, water, and the like.

The following examples are provided to illustrate the present invention.

EXAMPLES Example 1 (does not fall within the scope of the present invention)

  • (A) A potato dust inert system (PDIS) was prepared by blending the following three inert diluents in a ribbon blender: talc (Cyprus BT-200) (48.39% w/w), zeolite (16.12% w/w), and Alder bark (35.49% w/w).

    The dusts listed in Table 1 below were prepared by blending PDIS and the compounds at the concentrations indicated in a ribbon blender and were evaluated for activity against P. infestans at the rate of application of active ingredient indicated. Dust No. Compound Percent (w/w) Percent PDIS (w/w) Rate of Application (ppm/cwt1) 1 Cymoxanil 10.5 89.5 500 2 Cymoxanil 5.3 91.5 250 Topsin2 3.2 150 3 Dimethomorph3 10.5 89.5 500 4 Dimethomorph 5.3 91.5 250 Topsin 3.2 150 5 Propamocarb4 10.5 89.5 500 6 Propamocarb 5.3 91.5 250 Topsin 3.2 150 7 Topsin 5.3 94.7 250 8 Topsin 2.6 89.9 250 Mancozeb 7.5 600
    1 parts per million per 45,36kg (hundred lbs.)of seed (tuber) 2 thiophanate-methyl 3 (E,Z) 4-[3-(4-chlorophenyl)-3-(3,4-dimethoxyphenyl) acryloyl]morpholine 4 Propyl[3-(dimethylamino)propyl)carbamate

  • (B) The in-vitro screening procedure was conducted as follows:

Potato tubers were removed from 5°C storage and allowed to come to room temperature. The tubers were then washed with tap water and sterilized in 5% commercial bleach (Clorox) for 10 minutes. The tubers were then rinsed in sterile distilled water and dried.

Phytophthora infestans was grown on agar plates at 18°C for 10-14 days. 20 ml. of 5°C sterile distilled water were then added to each plate. The agar was then agitated or cut into smaller sections and placed at 10-12 °C for 2 hours to release zoospores.

Tubers were cut into uniform sized slices, 1 cm thick). Each dust was applied to 20 slices at 0,2268kg/cwt (0.5 lb/cwt). Two sets of 20 potato slices were left untreated with dust and used as controls. Each dusted potato slice was then placed on sterile moistened filter paper in a sterile petri dish.

A zoospore suspension was quantified to a concentration of 20,000 spores/ml. 100 ml of this spore suspension was then applied to a sterile filter paper disk. One such treated disk was placed in the center of each potato slice. One set of 20 undusted potato slices were not inoculated and used as a sterile control.

Each potato slice was then placed in the dark at 18°C for 7 days. After the 7 days, the disease state of each potato slice was assessed.

In Table 2 below, growth and sporulation of P. infestans for each potato slice was rated on a plus (+) or minus (-) scale. A minus indicates no growth of theP. infestans whereas a plus indicates growth. Growth was measured as minimal (+), good (++), or good and sporulation (+++). GROWTH AND SPORULATION OF P. INFESTANS Dust No. Growth 1 - 2 - 3 - 4 - 5 +++ 6 ++ 7 + 8 - Untreated +++ Sterile -

Example 2 (does not fall within the scope of the present invention)

  • (A) Dusts were prepared as described in Example 1 above.
  • (B) The in-vivo screening procedure was conducted as follows:

Potato tubers were removed from 5°C storage and allowed to come to room temperature. The tubers were then washed with tap water and sterilized in 5% commercial bleach (Clorox) for 10 minutes. The tubers were then rinsed in sterile distilled water and dried.

Phytophthora infestans was grown on agar plates at 18°C for 10-14 days. 20 ml. of 5°C sterile distilled water were then added to each plate. The agar was then agitated or cut into smaller sections and placed at 10-12°C for 2 hours to release zoospores. A zoospore suspension was quantified to a concentration of 20,000 spores/ml.

Small punctures were made in the tubers with a sterile needle and the punctured tubers were then dipped into the suspension of P. infestans zoospores. The tubers were then incubated at 15°C with 95% relative humidity for 7-10 days. After the incubation the tubers were then cut into 56,699-113,398g (2-4 oz.) pieces. Each dust was applied to 15 pieces at 0.2268 kg/cwt (0.5 lb/cwt) or according to manufacturer's directions. One set of 15 pieces was left untreated and used as a control.

Potatoes not dipped in the zoospores were also cut into 56,699-113,398 g (2-4 oz.) pieces and one set of 15 uninoculated potato pieces was used as a sterile control.

The potato pieces were then placed in sandy soil and incubated at 17°C days and 13°C nights for 32 days. Growth after emergence was monitored for 14-28 days. Disease symptoms were visually rated. Stem/leaf tissue was assayed for P. infestans on appropriate media. Finally, potato seed pieces were then removed and cut in half and disease presence was visually assessed.

The results of this test are presented below in Tables 3 and 4. Germination and Emergence Results Dust No. Emergence (%) Day 14 Germination (%) Day 32 1 33.3 100 2 33.3 100 3 26.7 80 4 33.3 53.3 6 20 40 8 6.7 6.7 Untreated 20 13.3 Sterile 33.3 100
TUBER AND STEM HEALTH Dust No. A1(%) B2 (%) C3 (%) D4 (%) 1 0 0 26.7 73.3 2 0 0 0 100 3 20 26.7 53.3 0 4 40 13.3 40 0 6 60 20 20 0 8 93.3 6.7 0 0 Untreated 86.7 13.3 0 0 Sterile 0 0 0 100
1 Blighted tuber; No emergence 2 Blighted tuber; Small-sized infected stems 3 Blighted tuber; Average-sized infected stems 4 Clean tubers; Healthy uninfected stems

Example 3

The following new dusts in Table 5 were prepared as described in Example 1. Dust No. Compound Percent (w/w) Percent PDIS (w/w) Rate of Application (ppm/cwt) 9(*) Cymoxanil 5.3 94.7 250 10(*) Cymoxanil 2.1 94.7 100 Topsin2 3.2 150 11(*) Cymoxanil 4.2 92.6 200 Topsin 3.2 150 12 Cymoxanil 2.1 92.2 100 Mancozeb 2.5 100 Topsin 3.2 150 13(*) Topsin 5.2 87.3 500 Mancozeb 7.5 600
(*) does not fall within the scope of the present invention

These dusts were tested using the procedure described in Example 2 above. The results of this testing is shown in Table 6 below. EMERGENCE AND TUBER AND STEM HEALTH Dust No. Emergence (%) Infection (%) Day 15 Day 23 Day 35 Tubers Stems 9(*) 0 20 80 20 0 10(*) 0 0 60 40 33.3 11(*) 0 20 100 40 33.3 12 20 80 100 0 0 13 (*) 0 0 0 100 no stems Untreated 0 0 0 100 no stems Sterile 0 100 100 0 0
(*) does not fall within the scope of the present invention

Example 4

The following dusts in Table 7 were prepared as described in Example 1. Dust No. Compound Percent (w/w) Percent PDIS (w/w) Rate of Application (ppm/cwt ) 14(*) Mancozeb(80%) 10.0 90.0 400 15(*) Cymoxanil(96%) 2.1 97.9 100 16(*) Cymoxanil(96%) 2.1 90.9 100 Mancozeb(80%) 7.5 300 17(*) Topsin(95%) 3.2 92.8 150 Cymoxanil(50%) 4.0 100 18 Topsin(95%) 3.2 84.7 150 Mancozeb(80%) 10.0 400 Cymoxanil(96%) 2.1 100 19 Topsin(95%) 3.2 87.3 150 Mancozeb(80%) 7.5 300 Cymoxanil(96%) 2.1 100
(*) does not fall within the scope of the present invention

These dusts (as well as Dusts Nos. 7 and 8) were tested using the procedure described in Example 2 above using Russet Burbank tubers. The results of this testing (10 replications/treatment) are shown in Table 8 below. EMERGENCE AND STEM HEALTH Dust No. Emergence (%) Infection (%) Day 14 Day 28 Stems 7(*) 0 0 no stems 8(*) 10 10 100 14(*) 0 10 100 15(*) 30 40 25 16(*) 20 40 0 17(*) 10 30 33 18 30 40 0 Untreated 0 0 no stems Sterile 60 100 0
(*) does not fall within the scope of the present invention

Example 5

The dusts prepared in Example 4 above (as well as Dusts Nos. 7 and 8) were tested using the procedure described in Example 2 above using Red Nordland tubers. The results of this testing (7 replications/treatment) are shown in Table 9 below. EMERGENCE AND STEM HEALTH Dust No. Emergence (%) Infection (%) Day 10 Day 38 Stems 7(*) 0 0 no stems 8(*) 14.3 14.3 100 14(*) 0 0 no stems 15(*) 85.7 100 14 16(*) 57.1 85.7 0 17(*) 42.9 85.7 14 18 71.4 100 0 Untreated 0 0 no stems Sterile 57.1 100 0
(*) does not fall within the scope of the present invention

Example 6

Shepody potato tubers were contaminated/inoculated with Phytophthora infestans and set aside ("source tubers"). After two weeks, one (1) source tuber was cut into quarters through the diseased area with a cutting knife. Without cleaning or changing the knife, five (5) uninoculated Shepody potato tubers were then cut into quarters. This process (1 source tuber/5 uninfected tubers) was repeated to provide enough tubers for 30 replications per treatment (Table 10 below).

The cut tubers (source and uninoculated) were weighed and the appropriate amount of each dust listed in Table 10 below was applied to the tubers by placing the tubers in a double paper bag with dust and then shaking the bag.

The treated tubers were then placed in an unsealed plastic bag (one bag per treatment) and incubated at 10°C, 80-90% RH, for two (2) weeks. After two (2) weeks, the bagged tubers were removed from the 10°C, 80-90% RH environment. The bags were then rolled or shaken to simulate movement from storage to planting areas. The tubers were removed and the spread of P. infestans was determined - % infected tubers. The tubers were warmed to room temperature and planted. The source tubers were not planted. Emergence and infection data were obtained as described above in Example 2 (30 replications/treatment).

The results of this test are listed below in Table 10. EMERGENCE AND TUBER AND STEM HEALTH Dust No. Emergence (%) Infection (%) Day 6 Day 20 Tubers (Before planting) Stems 7(*) 20 86.7 60 40 8(*) 26.7 80 40 20 14(*) 20 83.3 20 10 15(*) 30 100 20 0 17(*) 40 93.3 40 0 18 56.7 100 30 0 19 20 100 30 0 Untreated 16.7 70 90 40
(*) does not fall within the scope of the present invention

Example 7

The procedure described above in Example 6 was repeated using Red Nordland potato tubers. The results of this test are present below in Table 11. EMERGENCE AND TUBER AND STEM HEALTH Dust No. Emergence (%) Infection (%) Day 8 Day 25 Tubers (Before planting) Stems 7(*) 20 83.3 47.5 33 8(*) 20 83.3 52.5 33 14(*) 30 70 52.5 0 15(*) 26.7 90 50 0 17(*) 26.7 96.7 45 0 18 36.7 100 45 0 19 20 96.7 35 0 Untreated 10 20 60 33 Sterile 36.7 100 0 0
(*) does not fall within the scope of the present invention

The results in Tables 10 and 11 demonstrate that tubers contaminated with P. infestans spread from a contaminated seed source through the cutting and handling of the tubers prior to treatment and planting, still produced plants that were disease free when the tubers were treated in accordance with the present invention prior to planting.


Anspruch[de]
  1. Verfahren zur Bekämpfung von Pflanzenpilzen bei einer Pflanze, das umfasst ein Anwenden oder Aufbringen einer wirksamen Menge einer Fungizidzusammensetzung auf das Saatgut oder die Knollen einer Pflanze, wobei die Fungizidzusammensetzung eine fungizid wirksame Menge umfasst von:
    • a) einer 2-Alkoxyiminoacetamid-Verbindung der Formel:
      worin R für Methyl oder Ethyl steht, und R1 für Wasserstoff, C1-C4 Alkyl oder Allyl steht;
    • b) einem Alkylen-bis-dithiocarbamat-Komplexsalz der Formel:
      worin R4 und R5 jeweils unabhängig voneinander für Wasserstoff oder C1-C6 Alkyl stehen; Q für Zn, Fe oder Cu steht; und das Verhältnis von x zu y von etwa 3:1 bis etwa 100:1 beträgt; und
    • c) einer Thiophanat-Verbindung der Formel:
    worin R2 und R3 jeweils unabhängig voneinander für C1-C6 Alkyl stehen.
  2. Verfahren nach Anspruch 1, worin R1 und R2 und R3 jeweils unabhängig voneinander für C1-C4 Alkyl stehen, und R4 und R5 jeweils unabhängig voneinander für Wasserstoff oder C1-C4 Alkyl stehen.
  3. Verfahren nach Anspruch 2, worin R1, R2 und R3 jeweils unabhängig voneinander für Methyl oder Ethyl stehen, und R4 und R5 jeweils unabhängig voneinander für Wasserstoff, Methyl oder Ethyl stehen.
  4. Verfahren nach Anspruch 3, worin Q für Zn steht, und das Verhältnis von x zu y von 5:1 bis 20:1 beträgt.
  5. Verfahren nach Anspruch 4, worin das Verhältnis von x zu y von 6:1 bis 10:1 beträgt.
  6. Verfahren nach Anspruch 5, worin die 2-Alkoxyiminoacetamid-Verbindung für Cymoxanil steht; die Alkylen-bis-dithiocarbamat-Komplexsalzverbindung für Mancozeb steht; und die Thiophanat-Verbindung für Thiophanat-methyl steht.
  7. Verfahren nach Anspruch 1, worin die Pflanze für eine Kartoffelpflanze steht.
  8. Verfahren nach Anspruch 7, worin der Pilz für den Kraut- und Knollenfäule-Pilz, Phytophthora infestans, steht.
  9. Fungizidzusammensetzung, die eine fungizid wirksame Menge umfast von:
    • a) einer 2-Alkoxyiminoacetamid-Verbindung der Formel:
      worin R für Methyl oder Ethyl steht, und R1 für Wasserstoff, C1-C4 Alkyl oder Allyl steht;
    • b) einer Alkyten-bis-dithiocarbamat-Komplexsalzverbindung der Formel:
      worin R4 und R5 jeweils unabhängig voneinander für Wasserstoff oder C1-C6 Alkyl stehen; Q für Zn, Fe oder Cu steht; und das Verhältnis von x zu y von etwa 3:1 bis etwa 100:1 beträgt; und
    • c) einer Thiophanat-Verbindung der Formel:
    worin R2 und R3 jeweils unabhängig voneinander für C1-C6 Alkyl stehen.
  10. Zusammensetzung nach Anspruch 9, worin R1 und R2 und R3 jeweils unabhängig voneinander für C1-C4 Alkyl stehen, und R4 und R5 jeweils unabhängig voneinander für Wasserstoff oder C1-C4 Alkyl stehen.
  11. Zusammensetzung nach Anspruch 10, worin R1, R2 und R3 jeweils unabhängig voneinander für Methyl oder Ethyl stehen, und R4 und R5 jeweils unabhängig voneinander für Wasserstoff, Methyl oder Ethyl stehen.
  12. Zusammensetzung nach Anspruch 11, worin Q für Zn steht, und das Verhältnis von x zu y von 5:1 bis 20:1 beträgt.
  13. Zusammensetzung nach Anspruch 12, worin das Verhältnis von x zu y von 6:1 bis 10:1 beträgt.
  14. Zusammensetzung nach Anspruch 13, worin die 2-Alkoxyiminoacetamid-Verbindung für Cymoxanil steht; die Alkylen-bis-dithiocarbamat-Komplexsalzverbindung für Mancozeb steht; und die Thiophanat-Verbindung für Thiophanat-methyl steht.
  15. Verfahren zur Bekämpfung von Pflanzenpilzen bei einer Pflanze, das umfasst ein Anwenden oder Aufbringen einer wirksamen Menge einer Fungizidzusammensetzung auf das Saatgut oder die Knollen einer Pflanze, wobei die Fungizidzusammensetzung eine fungizid wirksame Menge umfasst von Cymoxanil in Beimischung von Mancozeb und Thiophanat-methyl.
  16. Verfahren nach Anspruch 15, worin die Pflanze für eine Kartoffelpflanze steht.
  17. Verfahren nach Anspruch 16, worin der Pilz für den Kraut- und Knollenfäule-Pilz, Phytophthora infestans, steht.
  18. Fungizidzusammensetzung, die Cymoxanil, Mancozeb und Thiophanat-methyl in einer wirksamen zusammengesetzten Menge umfasst.
Anspruch[en]
  1. A method for combatting plant fungi in a plant, which comprises applying to the seeds or tubers of the plant, an effective amount of a fungicidal composition comprising a fungicidally effective amount of:
    • a) a 2-alkoxyiminoacetamide compound of the formula:
         wherein R is methyl or ethyl and R1 is hydrogen, C1-C4 alkyl or allyl;
    • b) an alkylene bis-dithiocarbamate complex salt of the formula:
         wherein R4 and R5 are each, independently, hydrogen or C1-C6 alkyl; Q is Zn, Fe, or Cu; and the ratio of x to y is from about 3:1 to about 100:1; and
    • c) a thiophanate compound of the formula:
       wherein R2 and R3 are each, independently, C1-C6 alkyl.
  2. A method as recited in claim 1 wherein R1 and R2, and R3 are each, independently, C1-C4 alkyl, and R4 and R5 are each, independently, hydrogen or C1-C4 alkyl.
  3. A method as recited in claim 2 wherein R1, R2, and R3 are each, independently, methyl or ethyl, and R4 and R5 are each, independently, hydrogen, methyl or ethyl.
  4. A method as recited in claim 3 wherein Q is Zn and the ratio of x to y is from 5:1 to 20:1.
  5. A method as recited in claim 4 wherein the ratio of x to y is from 6:1 to 10:1.
  6. A method as recited in claim 5 wherein the 2-alkoxyiminoacetamide compound is cymoxanil; the alkylene bis-dithiocarbamate complex salt compound is mancozeb; and the thiophanate compound is thiophanate-methyl.
  7. A method as recited in claim 1 wherein the plant is a potato plant.
  8. A method as recited in claim 7 wherein the fungi is the Late Blight fungus, Phytophthora infestans.
  9. A fungicidal composition comprising a fungicidally effective amount of:
    • a) a 2-alkoxyiminoacetamide compound of the formula:
         wherein R is methyl or ethyl and R1 hydrogen, C1-C4 alkyl or allyl;
    • b) an alkylene bis-dithiocarbamate complex salt compound of the formula:
         wherein R4 and R5 are each, independently, hydrogen or C1-C6 alkyl; Q is Zn, Fe, or Cu; and the ratio of x to y is from about 3:1 to about 100:1.

      and
    • c) a thiophanate compound of the formula:
       wherein R2 and R3 are each, independently, C1-C6 alkyl.
  10. A composition as recited in claim 9 wherein R1 and R2, and R3 are each, independently, C1-C4 alkyl, and R4 and R5 are each, independently, hydrogen or C1-C4 alkyl.
  11. A composition as recited in claim 10 wherein R1, R2, and R3 are each, independently, methyl or ethyl, and R4 and R5 are each, independently, hydrogen, methyl or ethyl.
  12. A composition as recited in claim 11 wherein Q is Zn and the ratio of x to y is from 5:1 to 20:1.
  13. A composition as recited in claim 12 wherein the ratio of x to y is from 6:1 to 10:1.
  14. A composition as recited in claim 13 wherein the 2-alkoxyiminoacetamide compound is cymoxanil; the alkylene bis-dithiocarbamate complex salt compound is mancozeb; and the thiophanate compound is thiophanate-methyl.
  15. A method for combatting plant fungi in a plant, which comprises applying to the seeds or tubers of the plant, an effective amount of a fungicidal composition comprising a fungicidally effective amount of:
    • cymoxanil in admixture with mancozeb and thiophanate-methyl.
  16. A method as recited in claim 15 wherein the plant is a potato plant.
  17. A method as recited in claim 16 wherein the fungi is the Late Blight fungus, Phytophthora infestans.
  18. A fungicidal composition comprising cymoxanil, mancozeb and thiophanate-methyl, in an effective aggregate amount.
Anspruch[fr]
  1. Procédé de lutte contre des champignons des plantes dans une plante, qui comprend d'appliquer, aux semences ou aux tubercules de la plante, une quantité efficace d'une composition fongicide comprenant une quantité fongicidement efficace de :
    • a) un composé de 2-alcoxyiminoacétamide, de formule :
      dans laquelle R est un groupe méthyle ou un groupe éthyle et R1 est un atome d'hydrogène, un groupe allyle ou un groupe alkyle en C1-C4;
    • b) un sel en complexe d'alkylène bis-dithiocarbamate, de formule :
      dans laquelle R4 et R5 sont chacun, indépendamment, un atome d'hydrogène ou un groupe alkyle en C1-C6 ; Q est Zn, Fe ou Cu ; et le rapport de x à y est d'environ 3/1 à environ 100/1 ; et
    • c) un composé de thiophanate, de formule :
    dans laquelle R2 et R3 sont chacun, indépendamment, un groupe alkyle en C1-C6.
  2. Procédé selon la revendication 1, dans lequel R1 et R2, et R3 sont chacun, indépendamment, un groupe alkyle en C1-C4, et R4 et R5 sont chacun, indépendamment, un atome d'hydrogène ou un groupe alkyle en C1-C4.
  3. Procédé selon la revendication 2, dans lequel R1, R2, et R3 sont chacun, indépendamment, un groupe méthyle ou un groupe éthyle, et R4 et R5 sont chacun, indépendamment, un atome d'hydrogène, un groupe méthyle ou un groupe éthyle.
  4. Procédé selon la revendication 3, dans lequel Q est Zn et le rapport de x à y est de 5/1 à 20/1.
  5. Procédé selon la revendication 4, dans lequel le rapport de x à y est de 6/1 à 10/1.
  6. Procédé selon la revendication 5, dans lequel le composé de 2-alcoxyiminoacétamide est le cymoxanil ; le composé sel en complexe d'alkylène bis-dithiocarbamate est le mancozeb ; et le composé de thiophanate est le thiophanate-méthyle.
  7. Procédé selon la revendication 1, dans lequel la plante est une plante de pomme de terre.
  8. Procédé selon la revendication 7, dans lequel le champignon est le champignon Phytophthora infestans du mildiou (Late Blight).
  9. Composition fongicide comprenant une quantité fongicidement efficace de :
    • a) un composé de 2-alcoxyiminoacétamide, de formule :
      dans laquelle R est un groupe méthyle ou un groupe éthyle et R1 est un atome d'hydrogène, un groupe allyle ou un groupe alkyle en C1-C4 ;
    • b) un composé sel en complexe d'alkylène bis-dithiocarbamate, de formule :
      dans laquelle R4 et R5 sont chacun, indépendamment, un atome d'hydrogène ou un groupe alkyle en C1-C6 ; Q est Zn, Fe ou Cu ; et le rapport de x à y est d'environ 3/1 à environ 100/1 ; et
    • c) un composé de thiophanate, de formule :
    dans laquelle R2 et R3 sont chacun, indépendamment, un groupe alkyle en C1-C6.
  10. Composition selon la revendication 9, dans laquelle R1 et R2, et R3 sont chacun, indépendamment, un groupe alkyle en C1-C4, et R4 et R5 sont chacun, indépendamment, un atome d'hydrogène ou un groupe alkyle en C1-C4.
  11. Composition selon la revendication 10, dans laquelle R1, R2, et R3 sont chacun, indépendamment, un groupe méthyle ou un groupe éthyle, et R4 et R5 sont chacun, indépendamment, un atome d'hydrogène, un groupe méthyle ou un groupe éthyle.
  12. Composition selon la revendication 11, dans laquelle Q est Zn et le rapport de x à y est de 5/1 à 20/1.
  13. Composition selon la revendication 12, dans laquelle le rapport de x à y est de 6/1 à 10/1.
  14. Composition selon la revendication 13, dans laquelle le composé de 2-alcoxyiminoacétamide est le cymoxanil ; le composé sel en complexe d'alkylène bis-dithiocarbamate est le mancozeb ; et le composé de thiophanate est le thiophanate-méthyle.
  15. Procédé de lutte contre des champignons des plantes dans une plante, qui comprend d'appliquer, aux semences ou aux tubercules de la plante, une quantité efficace d'une composition fongicide comprenant une quantité fongicidement efficace de cymoxanil associé dans un mélange avec du mancozeb et du thiophanate-méthyle.
  16. Procédé selon la revendication 15, dans lequel la plante est une plante de pomme de terre.
  17. Procédé selon la revendication 16, dans lequel le champignon est le champignon Phytophthora infestans du mildiou (Late Blight).
  18. Composition fongicide comprenant du cymoxanil, du mancozeb et du thiophanate-méthyle, en une quantité d'agrégat efficace.






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