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CN1666613A - Anti-fungicidal mixture - Google Patents

Anti-fungicidal mixture Download PDF

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Publication number
CN1666613A
CN1666613A CN 200410004695 CN200410004695A CN1666613A CN 1666613 A CN1666613 A CN 1666613A CN 200410004695 CN200410004695 CN 200410004695 CN 200410004695 A CN200410004695 A CN 200410004695A CN 1666613 A CN1666613 A CN 1666613A
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Prior art keywords
compound
iia
mixture
iii
formula
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Inventor
E·阿默曼
R·施蒂尔勒
G·劳伦兹
S·斯特拉斯曼
G·斯坦穆勒
K·谢尔伯格
E·勃纳
J·阿佩尔
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BASF SE
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BASF SE
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Priority to CN 200410004695 priority Critical patent/CN1666613A/en
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Abstract

The invention relates to an anti-fungicidal mixture comprising synergic amount of A) at least one active strobilurines compound selected from the following compounds, carbamic acid ester of (I), wherein T is CH or N, n=0, 1 or 2, R is halogen, alkyl or halogenated alkyl, when n=2, R can be different, and/or phenyl acetogenin of Iia-Iif, and compound of III. The invention also relates to the method for prevention and cure of unwanted fungus by employing these mixtures.

Description

Fungicidal mixture
The present invention relates to Fungicidal mixture, it comprises the following component of Synergistic amount:
A) at least a active strobilurins compound that is selected from following compound:
A1) carbamate of formula I:
Figure A20041000469500041
Wherein T is CH or N, and n is 0,1 or 2, and R is halogen, C 1-C 4-alkyl or C 1-C 4-haloalkyl, wherein radicals R can be different when n is 2,
And/or
A2) phenyl acetic acid derivatives of formula IIa-IIf:
????????????????IIa
????????????????IIb
Figure A20041000469500044
??????IIc
Figure A20041000469500045
?????????IId
?????????IIe
Figure A20041000469500051
?????????IIf
Wherein X is CH or N; And Y and Z is identical or different and be hydrogen or halogen in each case;
And
B) formula III compound
?????????????????????????III
In addition, the invention still further relates to mixture methods for fighting harmful mushrooms and Compound I and/or IIa-f and the purposes of III in this class mixture of preparation of using Compound I and/or IIa-f and III.
Formula I compound, their preparation and they are known by document (WO-A96/01256 and WO-A 96/01258) the effect of harmful fungoid.
Formula I especially represents wherein each substituent combination corresponding to the carbamate of the delegation of following table:
Table 1
Sequence number ????T ????Rn
????I.1 ????N ????2-F
????I.2 ????N ????3-F
????I.3 ????N ????4-F
????I.4 ????N ????2-Cl
????I.5 ????N ????3-Cl
????I.6 ????N ????4-Cl
????I.7 ????N ????2-Br
????I.8 ????N ????3-Br
????I.9 ????N ????4-Br
????I.10 ????N ????2-CH 3
????I.11 ????N ????3-CH 3
????I.12 ????N ????4-CH 3
????I.13 ????N ????2-CH 2CH 3
????I.14 ????N ????3-CH 2CH 3
????I.15 ????N ????4-CH 2CH 3
????I.16 ????N ????2-CH(CH 3) 2
????I.17 ????N ????3-CH(CH 3) 2
????I.18 ????N ????4-CH(CH 3) 2
????I.19 ????N ????2-CF 3
????I.20 ????N ????3-CF 3
????I.21 ????N ????4-CF 3
????I.22 ????N ????2，4-F 2
????I.23 ????N ????2，4-Cl 2
????I.24 ????N ????3，4-Cl 2
????I.25 ????N ????2-Cl，4-CH 3
????I.26 ????N ????3-Cl，4-CH 3
????I.27 ????CH ????2-F
????I.28 ????CH ????3-F
????I.29 ????CH ????4-F
????I.30 ????CH ????2-Cl
????I.31 ????CH ????3-Cl
????I.32 ????CH ????4-Cl
????I.33 ????CH ????2-Br
????I.34 ????CH ????3-Br
????I.35 ????CH ????4-Br
????I.36 ????CH ????2-CH 3
????I.37 ????CH ????3-CH 3
????I.38 ????CH ????4-CH 3
????I.39 ????CH ????2-CH 2CH 3
????I.40 ????CH ????3-CH 2CH 3
????I.41 ????CH ????4-CH 2CH 3
????I.42 ????CH ????2-CH(CH 3) 2
????I.43 ????CH ????3-CH(CH 3) 2
????I.44 ????CH ????4-CH(CH 3) 2
????I.45 ????CH ????2-CF 3
????I.46 ????CH ????3-CF 3
????I.47 ????CH ????4-CF 3
????I.48 ????CH ????2，4-F 2
????I.49 ????CH ????2，4-Cl 2
????I.50 ????CH ????3，4-Cl 2
????I.51 ????CH ????2-Cl，4-CH 3
????I.52 ????CH ????3-Cl，4-CH 3
Formula IIa-f compound, their preparation and they are known by document equally to the effect of harmful fungoid.
Formula IIf especially represents the compound of the combination of wherein variable X, Y and Z corresponding to the delegation of following table:
Table 2
Sequence number ????X ????Y ????Z
????IIf.1 ????N ????F ????Cl
????IIf.2 ????N ????F ????H
????IIf.3 ????CH ????F ????H
????IIf.4 ????CH ????F ????H
????IIf.5 ????N ????Cl ????Cl
????IIf.6 ????N ????Cl ????H
????IIf.7 ????CH ????Cl ????H
????IIf.8 ????CH ????Cl ????Cl
Compound I I is especially known by the following table document:
Sequence number Common name Document
??IIa The imines bacterium ??EP-A?253?213
??IIb ??dimoxystrobin ??EP-A?477?631
??IIc Trifluoro quick (trifloxystrobin) ??EP-A?460?575
??IId Fork phenalgin acid amides ??EP-A?398?692
??IIe The nitrile Fluoxastrobin ??EP-A?382?375
??IIf.1 ??fluoxastrobin ??WO-A?97/27189
Special preferred compound I.12, I.23, I.32 and I.38.Preferred especially inclusion compound is (common name: mixture hectogram quick (Pyraclostrobin)) I.32.In another embodiment of mixture of the present invention, preferred formula IIa compound.
The formula III compound (common name: the Delan) and its preparation method be described among the GB-A 857 383.
The purpose of this invention is to provide harmful fungoid to be had and improve active mixture (Synergistic mixture), with the rate of application that reduces known compound and improve its activity profile using under the situation that total amount reduces of reactive compound.
We find that this purpose realizes by the mixture of beginning definition.In addition, we also find to use simultaneously, promptly co-administered or independent administered compound I and/or IIa-f and III, or order administered compound I and/or IIa-f and III can prevent and treat harmful fungoid better than using each compound separately.
About the two keys of C=CH or C=N, formula IIa-f compound can E or the Z configuration have (about carboxylic acid functional).Correspondingly, they can be used as pure E or Z isomer or E/Z isomer mixture and are used for mixture of the present invention.Preferred E/Z isomer mixture or the Z isomer of using, wherein preferred especially Z isomer.
The two keys of the C=N of the oxime ether in the Compound I Ic side chain can be used as pure E or Z isomer or exist as the E/Z isomer mixture.Compound I Ia-f can be used as isomer mixture or pure isomer is used for mixture of the present invention.
Because their alkaline characteristic, Compound I and IIa-f can form salt or adduct with inorganic or organic acid or with metal ion.
Representative examples of mineral pigments is halogen acids such as hydrofluoric acid, hydrochloric acid, hydrobromic acid and hydroiodic acid, carbonic acid, sulfuric acid, phosphoric acid and nitric acid.
Appropriate organic for example is formic acid and alkanoic acid, as acetate, trifluoroacetic acid, trichloroacetic acid and propionic acid, and also has glycolic acid, thiocyanic acid, lactic acid, succinic acid, citric acid, benzoic acid, cinnamic acid, oxalic acid, alkyl sulfonic acid (having the straight chain that has 1-20 carbon atom or the sulfonic acid of branched-alkyl), aryl sulfonic acid or aryl disulfonic (aromatic group such as phenyl and naphthyl, it has one or two sulfo group), alkyl phosphonic acid (having the straight chain that has 1-20 carbon atom or the phosphonic acids of branched-alkyl), arylphosphonic acid or aryl di 2 ethylhexyl phosphonic acid (aromatic group such as phenyl and naphthyl, it has one or two phosphate group), wherein alkyl or aryl can have other substituting group, for example p-methyl benzenesulfonic acid, salicylic acid, Para-amino-salicylic acid, the 2-phenoxy benzoic acid, 2-acetoxy-benzoic acid etc.
Suitable metal ion is the ion of second major element especially, especially the ion of calcium and magnesium; The ion of third and fourth major element, especially aluminium, tin and plumbous ion; The ion of the ion of first to the 8th subgroup element, especially chromium, manganese, iron, cobalt, nickel, copper and zinc; And other ion.The ion of preferred especially period 4 subgroup element.Metal can exist by the various chemical valences that they may present.
When the preparation mixture, pure reactive compound I and/or IIa-f and the III of preferred use, optionally can be to the reactive compound of wherein sneaking into other antagonism harmful fungoid or other insect such as insect, spider or nematode, or have the reactive compound or the fertilizer of herbicide effect or growth regulating effect.
The mixture of Compound I and/or IIa-f and III or while (i.e. associating or independent) administered compound I and/or IIa-f and III have significant activity to the plant pathogenic fungi of wide region, and described fungi especially is selected from Ascomycetes (Ascomycetes), deuteromycetes (Deuteromycetes), Phycomycetes (Phycomycetes) and Basidiomycetes (Basidiomycetes) fungi.In them some play systemic action and therefore also are suitable for use as blade face and soil effect fungicide.
They are even more important to a large amount of fungies of control in various crops such as cotton, vegetable variety (for example cucumber, beans and cucurbitaceous plant), barley, dogstail, oat, coffee, corn, fruit variety, rice, rye, soybean, grape vine, wheat, ornamental plants, sugarcane and various seed.
They are particularly suitable for preventing and treating the following plants pathogenic epiphyte: the standing grain powdery mildew in the cereal class (Erysiphe graminis) (powdery mildew), two spore powdery mildews (Erysiphecichoracearum) in the cucurbitaceous plant and monofilament shell (Sphaerotheca fuliginea), apple mildew bacterium in the apple (Podosphaera leucotricha), grape snag shell (Uncinula necator) in the grape vine, handle rest fungus (Puccinia) in the cereal class belongs to, cotton, rhizoctonia in rice and the lawn (Rhizoctonia) belongs to, smut in cereal class and the sugarcane (Ustilago) belongs to, venturia inaequalis in the apple (Venturiainaequalis) (scab), length in the cereal class spore (Helminthosporium) of wriggling belongs to, wheat glume blight bacterium (Septoria nodorum) in the wheat, strawberry, vegetables, Botrytis cinerea in ornamental plants and the grape vine (Botrytis cinerea) (gray mold), peanut tail spore (Cercosporaarachidicola) in the peanut, eye spot bacterium (Pseudocercosporellaherpotrichoides) in wheat and the barley, Pyricularia oryzae in the rice (Pyricularia oryzae), phytophthora infestans in potato and the tomato (Phytophthora infestans), false downy mildew (Pseudoperonospora) in cucurbitaceous plant and the lupulus belongs to, grape in the grape vine is given birth to single shaft mould (Plasmopara viticola), and the chain lattice spore (Alternaria) in vegetables and the fruit belongs to and Neurospora (Fusarium) and wheel branch spore (Verticillium) genus.
In addition, they can also be used for protective material (for example protecting timber) and not be subjected to the infringement of Paecilomyces varioti (Paecilomyces variotii) for example to make it.
Compound I and/or IIa-f and III can be simultaneously (together or separately) uses or order is used, and the order under using separately is usually to preventing and treating the result without any influence.
Compound I and/or IIa-f and III be usually with 10: 1 to 1: 100, and preferred 1: 1 to 1: 20,1: 1 to 1: 10 weight ratio (Compound I and/or IIa-f: III) use especially.
The character that depends on required effect, the rate of application of mixture of the present invention are 5-500g/ha for Compound I and/or IIa-f, preferred 50-500g/ha, especially 50-200g/ha.
Correspondingly, the rate of application of compound III is generally 5-2000g/ha, preferred 10-1000g/ha, especially 50-750g/ha.
For seed treatment, the rate of application of this mixture is generally the 0.001-100g/kg seed, preferred 0.01-50g/kg seed, especially 0.01-10g/kg seed.
If will prevent and treat the plant-pathogenic harmful fungoid, then the mixture of independent or the co-administered or Compound I of Compound I and/or IIa-f and III and/or IIa-f and III uses by before or after the plant seeding or before or after plant emerges seed, plant or soil spraying or dusting being carried out.
Fungicidal synergistic mixtures of the present invention or Compound I and/or IIa-f and III for example can be mixed with water-based, oiliness or other suspension that promptly sprays solution, powder and form of suspension or highly concentrate, dispersion, emulsion, oil dispersion, stick with paste, pulvis broadcasts sowing the form with material or granula, and can be by spraying, atomizing, dusting, broadcast sowing or water and use.Type of service depends on the purpose that is intended to; Under any circumstance all should guarantee the meticulous as far as possible and distribution equably of mixture of the present invention.
Preparaton prepares by known mode own, for example prepares by adding solvent and/or carrier.Usually inert additwe such as emulsifier or dispersant are mixed with preparaton.
Suitable surfactant be aromatic sulfonic acid such as lignin-, phenol-, naphthalene-and the alkali metal salt of dibutyl naphthalene sulfonic acids and fatty acid, alkali salt and ammonium salt, alkyl-and alkylaryl sulfonates, alkyl, lauryl ether and aliphatic alcohol sulfate and sulphation 16-, 17-and the salt of octadecanol or fatty alcohol glycol ether, the condensation product of sulfonated naphthalene and derivative thereof and formaldehyde, the condensation product of naphthalene or naphthalene sulfonic acids and phenol and formaldehyde, polyoxyethylene octylphenol ether, the ethoxylation iso-octyl-, octyl group-or nonyl phenol, alkyl phenol polyglycol ether, tributyl phenyl polyglycol ether, alkyl aryl polyether alcohol, different tridecanol, fatty alcohol/ethylene oxide condensation product, ethoxylated castor oil, polyoxyethylene alkyl ether or polyoxypropylene alkyl ether, laruyl alcohol polyglycol ether acetic acid esters, sorbitol ester, lignin sulfite waste liquor or methylcellulose.
Powder, broadcast sowing to mix or to grind with solid carrier by mixture and prepare Compound I and/or IIa-f and III or Compound I and/or IIa-f and III with material and pulvis.
Granula (for example coating granula, dipping granula or homogeneous phase granula) is usually by preparing reactive compound and solid carrier adhesion.
Filler or solid carrier for example are that ore deposit soil is as silica gel, silicic acid, silicate, talcum, kaolin, lime stone, lime, chalk, bole, loess, clay, dolomite, diatomite, calcium sulphate, magnesium sulfate, magnesia; The synthetic material that grinds; Fertilizer such as ammonium sulfate, ammonium phosphate, ammonium nitrate, urea; The product of plant origin such as flour, bark powder, wood powder and shuck powder; Cellulose powder or other solid carrier.
Preparaton comprises 0.1-95 weight % usually, one of among the Compound I of preferred 0.5-90 weight % and/or IIa-f and the III or the mixture of Compound I and/or IIa-f and III.Reactive compound is with 90-100%, and the purity of preferred 95-100% (according to NMR spectrum or HPLC) is used.
Compound I and/or IIa-f and III or their mixture or corresponding preparaton are by using with Compound I and/or IIa-f and III processing harmful fungoid, its plant, seed, soil, zone, material or space of dwelling the dried rhizome of rehmannia or wanting to prevent and treat harmful fungoid with the mixture of antifungal effective dose or under situation about using separately.Use and before or after harmful fungoid infects, to carry out.
The Fungicidally active of compound of the present invention or mixture can illustrate by following experiment:
With reactive compound separately or together at 70 weight % cyclohexanone, 20 weight %Nekanil LN (Lutensol AP6 is based on the wetting agent with emulsification and peptizaiton of ethoxylated alkylphenol) and 10 weight %Emulphor EL (Emulan EL is based on the emulsifier of ethoxylized fatty alcohol) be mixed with the emulsion of 10% concentration and be diluted with water to desired concn in the mixture.
Estimate by the leaf area percentage that mensuration infects.These percentages are changed into effectiveness.The expection of active compound combinations is renderd a service and is used Colby formula [R.S.Colby, Weeds (weeds) 15, 20-22 (1967)] determine and with the effectiveness that observes relatively.
The Colby formula:
E＝x+y-x·y/100
E is that the expection of working concentration when being the mixture of the reactive compound A of a and b and B renderd a service, represents with % with respect to untreated control,
X is the effectiveness of reactive compound A when using with concentration a, represents with % with respect to untreated control,
Y is the effectiveness of reactive compound B when using with concentration b, represents with the % with respect to untreated control.
Use the Abbot formula by following calculating render a service ( E):
E＝(1-α/β)·100
α corresponding to the fungal infection percentage of handling plant and
β is corresponding to the fungal infection percentage of (contrast) plant of being untreated.
Effectiveness is that the infect level of the level that infects of plant corresponding to the untreated control plant handled in 0 expression; Effectiveness is that 100 expression processing plants are infected.
Application Example 1-to the activity of apple black star bacteria (apple scab on the apple tree)
In summer, with 10-16 days interval cultivar is sprayed to drip point eight times for the leaf of the outdoor apple tree of " GoldenDelicious " with water slurry, wherein this water slurry is prepared by stock solution that comprises 10% reactive compound, 85% cyclohexanone and 5% emulsifier or the following mixture of the reactive compound of ratio of giving.Owing to the natural pressure that infects, described leaf is periodically infected by airborne spore or is wetting by the moisture spore suspension with apple black star bacteria.Weather conditions support the blade face scab to develop at the assessment of this season end the time degree that all leaves are basically all infected by scab.Contaminate with the % range estimation.
The visual value of contaminating the percentage of leaf area is changed into the effectiveness of representing with the % with respect to untreated control.Effectiveness is that to infect degree identical with untreated control in 0 expression; Effectiveness is that 100 expressions 0% are infected.The expection of reactive compound combination is renderd a service and is used Colby formula (Colby, R.S. " Synergistic and the antagonism that calculate combinations of herbicides react ", Weeds 15, pp.20-22,1967) determine and with the effectiveness that observes relatively.
Table 3: comparative trial
Embodiment The concentration of reactive compound in the spray liquid (the g active substance/ha) Reactive compound Render a service (with respect to the % of untreated control)
??1C ??100g/ha The Compound I .32 of table 1 ?85
??2C ??100g/ha Compound I Ia ?66
??3C ??188g/ha ??375g/ha Compound III ?16 ?33
??4C (100% infects) Untreated control ?0
Table 4: mixture of the present invention
Embodiment The concentration of mixture of the present invention (g/ha) The effectiveness that observes The effectiveness of calculating *
??5 ??100(I.32)+188(III) ??93 ?87
??6 ??100(IIa)+188(III) ??91 ?71
??7 ??100(IIa)+375(III) ??90 ?77
*Use the Colby formula
Application Example 2-to give birth to the activity of the mould grape vine downy mildew that causes of single shaft by grape
With the aqueous compositions of reactive compound cultivar is sprayed to the drip point for the leaf of the grape pot rattan of " M ü ller-Thurgau ", wherein said preparation is by the stock solution preparation that comprises 10% reactive compound, 85% cyclohexanone and 5% emulsifier.Giving birth to the mould moisture zoospore suspension of single shaft with grape in second day inoculates the downside of leaf.At first under 24 ℃, place the chamber of water saturated with vapor to reach 48 hours grape vine then, in 20-30 ℃ greenhouse, placed 5 days then.This section put into plant moist chamber once more and reached 16 hours after the period, to promote the sporangiophore eruption.Estimate development of disease degree on the leaf downside then.
To contaminate the visual value of percentage of leaf area by changing into the effectiveness of representing with % as mentioned above with respect to untreated control.The expection effectiveness use Colby formula of reactive compound combination is determined and is compared with the effectiveness that observes.
Table 5: comparative trial
Embodiment The concentration of reactive compound (ppm) in the spray liquid Reactive compound Render a service (with respect to the % of untreated control)
??8C ??4 ??2 ??1 Compound I Ic ?55 ?33 ?22
??9C ??4 ??2 ??1 Compound I Ie ?15 ?25 ?40
??10C ??40 ??20 ??10 ??5 Compound III ?66 ?44 ?33 ?22
??11C (89% infects) Untreated control ?0
Table 6: mixture of the present invention
Embodiment The concentration of mixture of the present invention (ppm) The effectiveness that observes The effectiveness of calculating *
??12 4 (IIc)+40 (III) mixtures 1: 10 ??94 ?85
??13 2 (IIc)+20 (III) mixtures 1: 10 ??89 ?62
??14 1 (IIc)+10 (III) mixture 1: 10 ??83 ?47
??15 4 (IIc)+20 (III) mixtures 1: 5 ??91 ?75
??16 2 (IIc)+10 (III) mixtures 1: 5 ??83 ?55
??17 1 (IIc)+5 (III) mixture 1: 5 ??66 ?39
????18 2 (IIc)+5 (III) mixtures 1: 2.5 ????61 ????47
????19 4 (IIc)+5 (III) mixtures 1: 1.25 ????89 ????65
????20 2 (IIe)+20 (III) mixtures 1: 10 ????94 ????84
????21 1 (IIe)+10 (III) mixture 1: 10 ????83 ????70
????22 1 (IIe)+5 (III) mixture 1: 5 ????78 ????65
*Use the Colby formula
Result of the test shows that the effectiveness that observes in all cases is higher than the effectiveness of using the Colby formula to calculate in advance.

Claims (8)

1. Fungicidal mixture, it comprises the following component of Synergistic amount:
A) at least a active strobilurins compound that is selected from following compound:
A1) carbamate of formula I:
Wherein T is CH or N, and n is 0,1 or 2, and R is halogen, C 1-C 4-alkyl or C 1-C 4-haloalkyl, wherein radicals R can be different when n is 2,
And/or
A2) phenyl acetic acid derivatives of formula IIa-IIf:
Wherein X is CH or N; And Y and Z is identical or different and be hydrogen or halogen in each case;
And
B) formula III compound
2. as the desired Fungicidal mixture of claim 1, its inclusion compound I.32:
3. as the desired Fungicidal mixture of claim 1, it comprises formula IIa compound.
4. methods for fighting harmful mushrooms, it comprises with formula I as claimed in claim 1 and/or IIa-f compound and formula III compound treatment harmful fungoid as claimed in claim 1, its plant, seed, soil, zone, material or space of dwelling the dried rhizome of rehmannia or wanting to prevent and treat harmful fungoid.
5. as the desired method of claim 4, it comprises with the Compound I at least a as claimed in claim 1 of 5-500g/ha and/or IIa-f handles harmful fungoid, its plant, seed, soil, zone, material or space of dwelling the dried rhizome of rehmannia or wanting to prevent and treat harmful fungoid.
6. as the desired method of claim 4, it comprises with the compound III as claimed in claim 1 of 5-2000g/ha handles harmful fungoid, its plant, seed, soil, zone, material or space of dwelling the dried rhizome of rehmannia or wanting to prevent and treat harmful fungoid.
7. formula I as claimed in claim 1 and/or IIa-f compound are preparing as claim 1 purposes in the desired mixture.
8. the described formula III compound of claim 1 is preparing as claim 1 purposes in the desired mixture.
CN 200410004695 2004-03-11 2004-03-11 Anti-fungicidal mixture Pending CN1666613A (en)

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Publication Number Publication Date
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Country Link
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