PH26831A - Fungicidal composition - Google Patents
Fungicidal composition Download PDFInfo
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- PH26831A PH26831A PH38334A PH38334A PH26831A PH 26831 A PH26831 A PH 26831A PH 38334 A PH38334 A PH 38334A PH 38334 A PH38334 A PH 38334A PH 26831 A PH26831 A PH 26831A
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- 239000000203 mixture Substances 0.000 title claims description 69
- 230000000855 fungicidal effect Effects 0.000 title claims description 20
- 150000001875 compounds Chemical class 0.000 claims description 16
- 239000002245 particle Substances 0.000 claims description 15
- CRQQGFGUEAVUIL-UHFFFAOYSA-N chlorothalonil Chemical compound ClC1=C(Cl)C(C#N)=C(Cl)C(C#N)=C1Cl CRQQGFGUEAVUIL-UHFFFAOYSA-N 0.000 claims description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 11
- 239000007787 solid Substances 0.000 claims description 10
- 239000004480 active ingredient Substances 0.000 claims description 8
- 239000004094 surface-active agent Substances 0.000 claims description 8
- 238000009825 accumulation Methods 0.000 claims description 7
- 230000009969 flowable effect Effects 0.000 claims description 6
- UWVQIROCRJWDKL-UHFFFAOYSA-N oxadixyl Chemical compound CC=1C=CC=C(C)C=1N(C(=O)COC)N1CCOC1=O UWVQIROCRJWDKL-UHFFFAOYSA-N 0.000 description 23
- XJLXINKUBYWONI-NNYOXOHSSA-N NADP zwitterion Chemical compound NC(=O)C1=CC=C[N+]([C@H]2[C@@H]([C@H](O)[C@@H](COP([O-])(=O)OP(O)(=O)OC[C@@H]3[C@H]([C@@H](OP(O)(O)=O)[C@@H](O3)N3C4=NC=NC(N)=C4N=C3)O)O2)O)=C1 XJLXINKUBYWONI-NNYOXOHSSA-N 0.000 description 19
- 238000009472 formulation Methods 0.000 description 16
- 235000007688 Lycopersicon esculentum Nutrition 0.000 description 15
- 241000233679 Peronosporaceae Species 0.000 description 15
- 240000003768 Solanum lycopersicum Species 0.000 description 15
- 201000010099 disease Diseases 0.000 description 15
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 15
- -1 1- (methoxycarbonyl)ethyl Chemical group 0.000 description 13
- 239000005807 Metalaxyl Substances 0.000 description 13
- ZQEIXNIJLIKNTD-UHFFFAOYSA-N methyl N-(2,6-dimethylphenyl)-N-(methoxyacetyl)alaninate Chemical compound COCC(=O)N(C(C)C(=O)OC)C1=C(C)C=CC=C1C ZQEIXNIJLIKNTD-UHFFFAOYSA-N 0.000 description 13
- 241000221785 Erysiphales Species 0.000 description 10
- 239000000417 fungicide Substances 0.000 description 9
- 239000005747 Chlorothalonil Substances 0.000 description 8
- 240000008067 Cucumis sativus Species 0.000 description 7
- 235000010799 Cucumis sativus var sativus Nutrition 0.000 description 6
- 230000001276 controlling effect Effects 0.000 description 6
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 238000005507 spraying Methods 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- 239000004546 suspension concentrate Substances 0.000 description 6
- 206010039509 Scab Diseases 0.000 description 5
- 241000221662 Sclerotinia Species 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 5
- 241000233629 Phytophthora parasitica Species 0.000 description 4
- 241001157813 Cercospora Species 0.000 description 3
- 241000196324 Embryophyta Species 0.000 description 3
- 241000233622 Phytophthora infestans Species 0.000 description 3
- 238000007605 air drying Methods 0.000 description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 3
- 238000011534 incubation Methods 0.000 description 3
- 238000003801 milling Methods 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 239000012488 sample solution Substances 0.000 description 3
- 239000004563 wettable powder Substances 0.000 description 3
- UHPMCKVQTMMPCG-UHFFFAOYSA-N 5,8-dihydroxy-2-methoxy-6-methyl-7-(2-oxopropyl)naphthalene-1,4-dione Chemical compound CC1=C(CC(C)=O)C(O)=C2C(=O)C(OC)=CC(=O)C2=C1O UHPMCKVQTMMPCG-UHFFFAOYSA-N 0.000 description 2
- 241000223218 Fusarium Species 0.000 description 2
- 206010027146 Melanoderma Diseases 0.000 description 2
- 241000233614 Phytophthora Species 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 235000013399 edible fruits Nutrition 0.000 description 2
- 238000011081 inoculation Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 230000003449 preventive effect Effects 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- 230000002195 synergetic effect Effects 0.000 description 2
- 238000010998 test method Methods 0.000 description 2
- 239000002562 thickening agent Substances 0.000 description 2
- 235000013311 vegetables Nutrition 0.000 description 2
- OWDLFBLNMPCXSD-UHFFFAOYSA-N 2-chloro-N-(2,6-dimethylphenyl)-N-(2-oxotetrahydrofuran-3-yl)acetamide Chemical compound CC1=CC=CC(C)=C1N(C(=O)CCl)C1C(=O)OCC1 OWDLFBLNMPCXSD-UHFFFAOYSA-N 0.000 description 1
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 1
- 244000291564 Allium cepa Species 0.000 description 1
- 235000002732 Allium cepa var. cepa Nutrition 0.000 description 1
- 241000223600 Alternaria Species 0.000 description 1
- 235000017060 Arachis glabrata Nutrition 0.000 description 1
- 244000105624 Arachis hypogaea Species 0.000 description 1
- 235000010777 Arachis hypogaea Nutrition 0.000 description 1
- 235000018262 Arachis monticola Nutrition 0.000 description 1
- 241000245589 Argyrolobium zanonii Species 0.000 description 1
- 239000005734 Benalaxyl Substances 0.000 description 1
- 241000219310 Beta vulgaris subsp. vulgaris Species 0.000 description 1
- 235000010149 Brassica rapa subsp chinensis Nutrition 0.000 description 1
- 235000000536 Brassica rapa subsp pekinensis Nutrition 0.000 description 1
- 241000499436 Brassica rapa subsp. pekinensis Species 0.000 description 1
- 235000007516 Chrysanthemum Nutrition 0.000 description 1
- 240000005250 Chrysanthemum indicum Species 0.000 description 1
- 241000207199 Citrus Species 0.000 description 1
- 235000009849 Cucumis sativus Nutrition 0.000 description 1
- 241000371644 Curvularia ravenelii Species 0.000 description 1
- 241000612153 Cyclamen Species 0.000 description 1
- 208000001840 Dandruff Diseases 0.000 description 1
- 244000307700 Fragaria vesca Species 0.000 description 1
- 235000016623 Fragaria vesca Nutrition 0.000 description 1
- 235000011363 Fragaria x ananassa Nutrition 0.000 description 1
- 244000068988 Glycine max Species 0.000 description 1
- 235000010469 Glycine max Nutrition 0.000 description 1
- 240000008415 Lactuca sativa Species 0.000 description 1
- 235000003228 Lactuca sativa Nutrition 0.000 description 1
- 208000003351 Melanosis Diseases 0.000 description 1
- 208000031888 Mycoses Diseases 0.000 description 1
- 244000061176 Nicotiana tabacum Species 0.000 description 1
- 235000002637 Nicotiana tabacum Nutrition 0.000 description 1
- 240000007594 Oryza sativa Species 0.000 description 1
- 235000007164 Oryza sativa Nutrition 0.000 description 1
- 241000228143 Penicillium Species 0.000 description 1
- 241000893212 Pestalotia Species 0.000 description 1
- 235000006089 Phaseolus angularis Nutrition 0.000 description 1
- 241001480007 Phomopsis Species 0.000 description 1
- 241000233647 Phytophthora nicotianae var. parasitica Species 0.000 description 1
- 240000007942 Prunus pensylvanica Species 0.000 description 1
- 235000013647 Prunus pensylvanica Nutrition 0.000 description 1
- 240000005809 Prunus persica Species 0.000 description 1
- 235000006040 Prunus persica var persica Nutrition 0.000 description 1
- 241001281805 Pseudoperonospora cubensis Species 0.000 description 1
- 235000014443 Pyrus communis Nutrition 0.000 description 1
- 241000220317 Rosa Species 0.000 description 1
- 241001533598 Septoria Species 0.000 description 1
- 244000061458 Solanum melongena Species 0.000 description 1
- 235000002597 Solanum melongena Nutrition 0.000 description 1
- 244000061456 Solanum tuberosum Species 0.000 description 1
- 235000002595 Solanum tuberosum Nutrition 0.000 description 1
- 235000021536 Sugar beet Nutrition 0.000 description 1
- 235000021307 Triticum Nutrition 0.000 description 1
- 244000098338 Triticum aestivum Species 0.000 description 1
- 241000959260 Typhula Species 0.000 description 1
- 241000082085 Verticillium <Phyllachorales> Species 0.000 description 1
- 240000007098 Vigna angularis Species 0.000 description 1
- 235000010711 Vigna angularis Nutrition 0.000 description 1
- 235000009754 Vitis X bourquina Nutrition 0.000 description 1
- 235000012333 Vitis X labruscana Nutrition 0.000 description 1
- 240000006365 Vitis vinifera Species 0.000 description 1
- 235000014787 Vitis vinifera Nutrition 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 235000020971 citrus fruits Nutrition 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 229930186364 cyclamen Natural products 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 238000003306 harvesting Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- CJPQIRJHIZUAQP-UHFFFAOYSA-N methyl N-(2,6-dimethylphenyl)-N-(phenylacetyl)alaninate Chemical compound CC=1C=CC=C(C)C=1N(C(C)C(=O)OC)C(=O)CC1=CC=CC=C1 CJPQIRJHIZUAQP-UHFFFAOYSA-N 0.000 description 1
- CIEXPHRYOLIQQD-UHFFFAOYSA-N methyl N-(2,6-dimethylphenyl)-N-2-furoylalaninate Chemical compound CC=1C=CC=C(C)C=1N(C(C)C(=O)OC)C(=O)C1=CC=CO1 CIEXPHRYOLIQQD-UHFFFAOYSA-N 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000020232 peanut Nutrition 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
- A01N43/76—1,3-Oxazoles; Hydrogenated 1,3-oxazoles
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
- A01N25/02—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing liquids as carriers, diluents or solvents
- A01N25/04—Dispersions, emulsions, suspoemulsions, suspension concentrates or gels
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/34—Nitriles
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/36—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids
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- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Health & Medical Sciences (AREA)
- Zoology (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Environmental Sciences (AREA)
- Dispersion Chemistry (AREA)
- Toxicology (AREA)
- Chemical & Material Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
Description
: 26831 2d
FUNGICIDAL COMPOSITION
This invention relates to a fungicidal composition © Me \ and more particularly to an agricultural and horticultural ¥% fungicidal composition with improved plant disease ug on Ea controlling effect on plants. {a Ba
Fungicidal compositions containing * Wid? tetrachloroisophthalonitrile (hereinafter called "TPN") as 2 an active ingredient are known. They are i.e. used for preventing and controlling fungal diseases of fruit- pearing trees and vegetables, and in general are applied as a foliar spray Or by admixture.
Compounds of the formula [I]
I CH, 2, wb) (11
Z CH, Xx wherein R is methoxymethyl. benzyl. chloromethyl, )-tetrahydrofuryl or 2-furvyl,
Z is »—oxo-1,3-oxazolidin=3-y1, 1- (methoxycarbonyl)ethyl. 2-oxo-thiolan -3-yl or tetrahydro-2-oxo-3-furanyl.
Xx, is H or Cl and X, js H or Cl. are known to have an excellent preventive, curative
- 2 = 26831 zs QO J. systemic fungicidal effect particularly in controlling downy mildew and epidemic diseases, which bring serious damages upon fruit-bearing trees and vegetables.
Various mixtures of TPN or of a compound of formula [I] with other fungicides have been suggested and used to extend the spectrum of activity, to enhance the activity or to improve the fungicidal effect against resistant strains.
While the use of a mixture compound of TPN and 2- i. methoxy—-N-(2-oxo-1,3-oxazolidin-3-yl)-aceto-2',6'-xylidine (common name: oxadixyl) is reported in Trans .Br .Mycol. Soc. 85,299-306 (1385), this reference does not suggest that a mixture of TPN and oxadixyl shows a more than additive (i.e. synergistic) fungicidal effect. Furthermore, the TPN used in the cited case is employed as wettable powder, and the only example cited of the mixture ratio for oxadixyl and TPN is 1:3.
The present invention provides a flowable formulation (i.e. an aqueous suspension concentrate) containing a phenylamide compound of formula I and TPN in the weight ratio range of from 1:2 to 1:15, and a surfactant wherein the solid components have a particle size in the range of from 0.5 to 5.0 tm (micron) at the 50 % volume accumulation point. The latter volume medium diameter is hereinafter designated VMD.
- 3 = 26831
It has been found that the formulations of the invention have a fungicidal effect which is substantially superior over the additive effect that would be expected by admixture of the active ingredients.
The synergistic effect is especially pronounced with formulations comprising a compound of formula I wherein R is methoxymethyl, benzyl, chloromethyl or 2-furvyl,
Z is 2-oxo-1,3-oxazolidin-3-yl, 1-(methoxylcarbonyl)ethyl or tetrahydro —2-0oXxo-3~furanyl, xy is H or Cl, and X, is H (hereinafter compounds of formula (Ia]).
Preferred compounds of formula I for use in the formulation of the invention include the compound of formula [Ia] wherein a) R is methoxymethyl, Z is 1-{methoxycarbonyl)ethyl and Xx, i H (metalaxyl) ob) R is methoxymethyl, Z is 2-oxo-1,3-oxazolidin-3-yl and Xx, is H (oxadixyl)
Cc) R is benzyl, Z is 1-(methoxycarbonyl)ethyl and x, is H (benalaxyl) d) R is chloromethyl, Z is tetrahydro-2-oxo-3-furanyl and xX, is H (ofurace) e) R is 2-furyl, Z is 1-(methoxycarbonyl) ethyl and xX, is H (furalaxyl) and £) R is methoxymethyl, 2Z is 2-oxo-1,3-oxazolidin-3-yl1 and xX, is Cl.
Most preferred compounds of formula 1 for use of the invention are metalaxyl and oxadixyl.
There is no particular restriction to the process for producing the fungicidal composition proposed in this invention. The composition of the invention can be produced in conventional manner, e.g. by a process comprising the steps of mixing the components and grinding its solid particles in an appropriate mill to the desired particle size.
Examples of mills suitable for use in the process of the invention include ball mills, impact-type crushers, air mills, wet-type mills, and so forth.
The VMD has been measured with the Coulter counter ® model TA-II (by Kabushiki Kaisha Nikkaki).
Preferably, the VMD should be within the range of from 0.8m to 2.5um, and it is more preferable to keep the \P VMD in the range from 0.8 ;«m to 1.8 (rand particularly in the range of from 0.5 to 1.5 pm.
While the contents of TPN and the phenylamide compound of formula I in the composition of this invention are not particularly limited, the composition should desirably comprise from 1 % to 70 % by weight of active ingredients. The weight ratios of TPN and the phenylamide compound of formula I should preferably be in the range of from 1:3 to 1:13, more preferably in the range from 1:4 to 1:12, particularly in the range of from 1:4 to 1:11 e.g. in the range of from 1:5 to 1:11. Though the amount of surfactant to be applied is not critical, preferred formulations will comprise from 1 to 10 % weight by weight and more preferably from 2 to 5 % weight by weight of surfactant. Examples of suitable surfactants are any agrculturally acceptable surfactant appropriate for use in a flowable, in particular liquid surfactants such an
Nonypole 100 and Demole N.
In addition to the active ingredients, surfactant (s) and diluent (water), the formulation may contain other components such as for example agriculturally acceptable thickening agents.
Typical examples of such formulations comprise ll e.g. from 0.1 to 1 % by weight of thickening agent.
Although there is not necessarily any restriction : to the sprayed amount of the chemical, it is usually appropriate to use it approximately in the amount of 1-500 g/10 ares (hereinafter designated "a") as active ingredient compound (A.I.) for its spraying application over a farm field where crops are grown and approximately in the amount of 0.1-5.0 kg (A.I.)/10a. in case it is used in the soil.
Of course, these are general standards, which are to be subject to adjustment as necessary in consideration of the varieties of crops, the types of diseases, and the degrees of damages, the period or the season, the weather, the forms of the chemical formulation, and so forth.
Next, the reference formulations and forms of manufactured formulations in embodiment of the composition proposed in this invention are described below, but it goes without saying that the forms of such formulations are not limited to these.
Example 1 (Reference Example)
Metalaxyl suspension concentrate having the following composition was prepared by mixing, followed by milling with the wet-type mill (Eiger motormill made by
Eiger Engineering Limited), in order to make particle size 1.5 fim in VMD while controlling the total amount of milling time:
Metalaxyl 25 parts
Nonypole 100 1 part (Supplied by Sanyo Kasei Kogyo
Co.Ltd.)
Demole N 2 parts (Supplied by Kao Co.Ltd.)
Water 72 parts
Example 2 (Reference Example)
Oxadixyl suspension concentrate having the following composition was also prepared similar to the above (particle size is 1.5,4m in VMD):
Oxadixyl 25 parts
Nonypole 100 1 part
Demole N 2 parts
Water 72 parts
Example 3-6 (Reference Example)
TPN suspension concentrate was prepared by uniformly mixing the following ingredients and milled with the wet—-type mill in order to make particle of various size in VMD while controlling the total amount of milling time:
TPN 50 parts
Nonypole 100 1.5 parts
Demole N 3 parts
Water 45.5 parts
In Reference Examples 3-6, particle size in VMD are as follows:
Example 3 0.5.\m
Example 4 1.0m
Example 5 1.5, m
Example 6 5.0, um
Example 7
TPN with Oxadixyl suspension concentrate having the following composition was prepared according to the same procedure as used in Example 1 (particle size is 1.04im in VMD):
TPN 32.0 parts
Oxadixyl 6.4 parts
Nonypole 100 1.5 parts
Demole N 3 parts
Water 57.1 parts
Example 8
TPN with Methalaxyl suspension concentrate having the following composition was prepared according to the same procedure as used in Example 1 (particle size is 1.5/4im in VMD) :
TPN 20 parts
Methalaxyl 2 parts
Nonypole 100 1 part
Demole N 2 parts
Water 75 parts
Example 9
TPN with Oxadixyl suspension concentrate having the following composition was prepared according to the same procedure as used in Example 1 (particle size is 0.5 im in VMD): . TPN 42 parts
Oxadixyl 6 parts
Nonypole 100 1.5 parts
- g9 -
Demole N 3 parts
Water 47.5 parts
The composition revealed by this invention is effective for controlling a wide variety of diseases of various agricultural and horticultural crops. Examples of such diseases are as follows:
Rice: Blast ,Helminthosporium leaf spot, Sheath blight, "Bakanae" disease, Seedling blight
Wheat: Leaf rust, Stripe rust, Loose smut,
Speckled leaf blotch, Spot blotch,
Powdery mildew, Typhula snow blight
Potato: Late blight, Early blight, Black scurf
Soybean: Downy mildew, Cercospora leaf spot, 1 Septoria brown spot, Sclerotinia rot,
Rust, Purple stain
Adzuki bean: Leaf spot, Rust, Leaf spot, Powdery mildew
Peanut: Brown leaf spot, Leaf spot, Sclerotinia rot
Tobacco: Brown spot, Black shank, Sclerotinia stem- rot, Sore shin, Damping-off, Bed rot,
Frog-eye. Powdery mildew
Sugar beet: Downy mildew, Cercospora leaf spot,
Damping-off
Tomato: Gray mold, Leaf mold, Late blight, Stem rot, Early blight, Cercospora leaf mold,
Fusarium wilt, Damping-off
Eggplant: Gray mold, Verticillium wilt, Brown rot,
Black rot, Powdery mildew, Leafmold
Cucurbit: Downy mildew, Phytophthora rot, Gray mold, Sclerotinia rot, Scab, Anthracnose,
Gummy stem blight, Fusarium wilt, Powdery mildew, Damping-off
Chinese cabbage: Downy mildew, Leaf spot, Sclerotinia rot,
Clubroot
Onion: Downy mildew, Gray mold neck rot,
Phytophthora rot ‘
Lettuce: Downy mildew, Gray mold, Leaf spot, Stem rot
Strawberry: Gray mold, Powdery mildew, Leaf blight
Chrysanthemum: Rust, Powdery mildew
Cyclamen: Gray nold
Rose: Blackspot, Powdery mildew
Citrus: Penicillium rot, Gray mold, Melanose,
Scab
Apple: Rust, Blight, Silver leaf, Alternaria leaf spot, Scab Powdery mildew, Blossom blight
Pear: Rust, Black spot, Scab
Peach: Brown rot, Scab,Phomopsis rot, Leaf curl
Grape: Downy mildew, Gray mold, Leaf spot,
Anthracnose, Ripe rot, Pestalotia disease, Rust, Dead arm, Powdery mildew
Also, the composition revealed by this invention, which is a flowable formulation, makes the following points conceivable.
Since the composition is already dispersed in liquid, it is little liable to cohesion in diluting water, and hence it is possible for the chemical to maintain the optimized particle size as it is.
As it is not necessary to add any solid matter as a diluent, it is possible to avoid the decomposing action by the solid matter.
Owing to these features, the active ingredients can work with remarkable efficiency, achieving an enhanced preventive effect. For its actual application, its excellent dispersion in water enables it to mix well with water, so that it is easy to formule its solution for spraying. As the composition also has excellent suspending feature, the chemical solution can maintain a uniform state of suspension for a long time after its formulation, so that it is possible to spray the solution at the predetermined concentration throughout the duration from the start of spraying to its finish and also that the spraying work will not be hampered with any clogging of the sprayer with the chemical. After the wettable powder formulation is sprayed, there remain some strains (traces of sprayed solution) on the fruits and leaves, but the composition of this invention makes it possible to harvest farm products with an extremely small amount of stain since it does not contain any mineral substance which works as the cause of this stain. Furthermore, this composition, not being powdery, | permits its safer application.
Typical test procedure and results are described below in order specifically to explain the effect of the composition proposed in this invention.
Yet, these are mere examples, and the applications of this invention are, of course, not limited to these alone.
Test Example 1
A sample solution diluted to a predetermined concentration (20,10,5,2,1 and 0.5 ppm a.i.) was uniformly sprayed on the leaves of 5-true-leaf-stage on tomatoes (variety:Redcherry) with an amount of 200(/10a, which were dried in a greenhouse for 2 hours. After air drying, zoospores of Phytophthora infestans were inoculated on the
. - 13 - leaves by spraying. The incubation was carried out at a temperature of 21°C and a relative humidity (R.H.) of 100 % for 2 days. At 5 days after inoculation, the infected areas of 3,4, and 5 leaf stage were eveluated, and disease intensity was assessed. The disease control was estimated by the expression: treated disease intensity (+ Tm BE TT) X100 untreared disease intensity ' BC 90 values were calculated.
Results of Test Example 1 are shown in Table 1 ~Table 7.
Test Example 2
A sample solution diluted to a predetermined concentration (20,10,5,2,1 and 0.5 ppm a.i.) was uniformly sprayed on the leaves of 2-true-leaf-stage on cucumbers (variety: Tokiwahikari 3 gou Pgate) with an amount of 200(/10a, which were dried in a greenhouse for 2 hours.
After air drying, zoosporangia of Pseudopernospora cubensis were inoculated on the leaves by spraying. The incubation was carried out at a temperature of 21°¢c and a relative humidity. (R.H) of 100 % for 2 days. At 5 days after inoculation, the infected areas of 1 and 2 leaf stage were evaluated, and disease intensity was assessed.
The disease control was estimated by the expression:
treated disease intensity ( 1- mmm TE, 100 untreared disease intensity
EC 90 values were calculated.
Results of Test Example 2 are shown in Table 8 Table 13.
Test Example 3
By the same test method of Test Example 1, a sample solution was uniformly sprayed on the leaves of tomatoes, which were dried in a greenhouse for 24 hours.
After air drying, the test plants was treated with artificial rain stress of 40 ml for 1 hour. At 3 hours after artificial rain stress, zoosporses of Phytophthora infestans were inoculated on the leaves. The incubation and evaluation were carried out as mentioned above.
Results of Test Example 3 are shown in Table 14~Table 20.
X + Y
BEC 90(th)= —_— x + YY
EC(a)9s0 EC(b)90
SF=EC90 (th) /EC90 (ob)
Table 1. Fungicidal activity (ECS0) against late blight (Phytophthora infestans) and downy mildew (Pseudoperonospora cubensis)
EC90 (ppm a.i.) . Particle Size . Downy
Formulation Late blight mildew 1 |Metalaxy! 25w/whFL 15 3.8 3.3 oo a oi 2 |Oxadixyl 25w/wPhFL 1.5 11.4 10.7 3 [Chlorothalonil 50w/ wh FL 0.5 TT T199 17.4 7 Oxadixyl 6.4w/wPFL 1.0 2.8 2.9 } Chlorothalonil 39. 0w/whEL 8 Chlorothalonil 15w/ wh WP 20s | 213 ("FL" and "WP" mean respectively flowable formulation and wettable powder.)
Table 2. Theoretical EC90 for various mixture of TPN and Metalaxyl against late blight in tomato (ppm a.i.) ungicides FL — ee WP
Ratios 0.5 ym 1.0 ym tum | sou 6.4 5.2 5.5 6.2 2 83 | 60| 65] 79] - 3 9.7 6.5 7.0 9.1 9.8 1 4 7.0 7.8 10.8 7.4 8.4 124 | - we] ws] sel mel 14 7.8 89 13.9 -
Te
Table 3. Fungicidal activity for various mixture of TPN and Metalaxyl against late blight in tomato (observed EC90) (ppm a.i.)
WP
1.0 ym 1.5 pm 5.0 pm
EE EC ee ete a mee] ar es elo
~18-
Table 4. Synergism factor (SF) for various mixture of TPN and Metalaxyl against late blight in tomato
Qungicides FI, re erro ep WP
Ratios 0.5 pm 1.0 pm | row Ex 1: 1 1.8 18] 18 | 17 -
CEE 18 | 21 | 21 | 20 -
EE 2.6 26 | 2.1 1.0 2.7 27 | 23 _ 2.0 2.8 07 | 24 | - 6 2.1 2.8 2.7 24 | - 7 | 22 29 | 298 | 24 | - 8 2.2 3.0 2.8 - 9 2.2 2.9 2.8 2.5 - : 14 24 2.2 2.0 - 5 | 18 | lo 20 | 1s TT
~19-
Table 5. Theoretical EC90 for various mixture of TPN and Oxadixyl against late blight in tomato ’ (ppm a.i.) ungicides FL
WP
Ratios 0.5 ym 1.0 pm 1.5 pm 5.0 ym o EE 2 16.0 9.2 10.4 14.7 IE 4 8.9 10.2 15.6 17.8 88 | 101 | 159 ks. wu us| we] woo | mel
A
Table 6. Fungicidal activity for various mixture of TPN and Oxadixyl against late blight in tomato (observed EC90) (ppm a.i.)
Fungicides Cor B 0.5 pm 1.0 pm 1.5 pm 5.0 ym WE
Ratios ~~ \| | ~~ on I 1 1 6.7 4.4 5.2 7.1 - 6.7 3.6 43 7.1 - 4 6.8 2.9 3.4 6.5 - — S ar] es] es 7 6.3 2.6 3.2 6.4 8 6.9 2.6 6.5 9 | 69 2.6 6.5
Table 7. Synergism factor (SF) for various mixture of TPN and Oxadixyl against late blight in tomato
Fungicides FL oars 0.5 pm 1.0 pm 1.5 pm 5.0 pm WE
Ratios 2.2 2.2 20 19 IE 2.4 2.6 24 2.1 - 3 2.4 28 | 28 | 23 13 4 | es | 31 30 | 24 ~ 5s | 28] 81] 31 Teal 6 2.6 3.2 31 | 24 - as 13 2.6 3.1 3.1 2.4
C14 24 | 26 | 27 22 - 2.4 22 | 25 | 21 | -
Table 8. Theoretical EC90 for various mixture of TPN and Metalaxyl against downy mildew in cucumber (ppm a.i.)
FL
Ratios 0.5 um 1.0 pm 1.5 pm 5.0 pm WE 5.6 4.8 5.0 55 | - 2 5.1 6.0 1] = 3 8.4 6.3 67 | = 84 9.0
Tea | es | 12 | es 10.2 69 | 16 10.1 _ 10.8 7.2 79 10.7 7 11.3 7.3 8.1 f11.2 8 11.8 75 | 83 | 117 122 | 78 84 | 121 a 12 C19 8.8 129 - 13.0 89 13.2 ; ose or 8.1 9.0 13.6
Table 9. Fungicidal activity for various mixture of TPN and Metalaxyl against downy mildew in cucumber (observed £EC90) (ppm a.i.)
Fungicides i FL
Ratios 0.5 pm 1.0 pm 1.5 pm | 5.0 pm wr 9 2.3 2.7 3.3 3 3.8 2.4 28 | 36 8.7 — ar as He 4.4 2.3 2.6 1] =] 6 47 24 2.7 IEE 7 4.8 24 2.8 45 | - 8 | 50 2.4 2.8 47 - 2.6 2.9 5.1 ea 14 6.3 3.5 4.1 6.0 - 4.0 43 6.4 _
Table 10. Synergism factor (SF) for various mixture of TPN and Metalaxy] against downy mildew in cucumber a
WP
Ratios 1.0 ym 1.5 um 5.0 pm oo eS en 0 Eee ae me ms] w]e] mao
Table 11. Theoretical EC90 for various mixture of TPN and Oxadixyl against downy mildew in cucumber ’ (ppma.i.)
Fungicided FL
WP
Ratios 1.0 pm 1.5 pm 5.0 pm 15.0 93 10.3 14.9 17.1 oro 8 9.1 10.3 16.0
Ewes] wel wa] ws
~26-
Table 12. Fungicidal activity for various mixture of TPN and Oxadixyl against downy mildew in cucumber (observed EC90) . (ppm a.i.)
Fungicides FL
WP
Ratios 1.5 pm 5.0 pm 2 66 | 40 | 46 6.1 - 4.0 6.2 150 : 6.6 2.8 3.4
Ta en
Table 13. Synergism factor (SF) for various mixture of TPN and Oxadixyl against downy mildew in cucumber : .
WP
Ratios 0.5 pm 1.0 pm 1.5 pm 5.0 pm 2.1 2.1 2.1 2.2 _ ela 3 2.3 2.7 2.8 2.4 1.1 | 31 | 30 25 25 | 32 30 | 25 25 3.3 3.1 2.6
FES e+ 4 sc 9 2.6 3.3 3.1 2.6 ore 15° 2.1 2.2 2.2 -
oo 28
Table 14. Fungicidal activity (I5C90) after artificial rain stress against late blight (Phytophtora infestans) (ppm a.i.)
Metalaxyl 25w/wPFL 1.5 3 Chlorothalonil 50w/whFL 0.5 49.8 4 Chlorothalonil 50w/whFL 1.0 = 19.3
Chlorothalonil 50w/w%FL 1.5 23.4 6 Chlorothalonil 50w/w%FL 5.0 51.6 7 Oxadixyl 6.4w/w%FL 1.0 5.3
Chlorothalonil 32.0w/w%FL
Table 15. Theoretical EC90 for various mixture of TPN and Metalaxyl against late blight in tomato (ppm a.i.)
Fungicides . ‘FL — —— WP 0.5 pum 1.0 pm | 1.5 pm 5.0 pm 101 83 88 1 0. 9 - 9 22.9 13.8 93.2 23.8 12 26.1 14.8 16.9 26.6 -
Table 16. Fungicidal activity after artificial rain stress for various mixture of
TPN and Metalaxyl against late blight in tomato (observed EC90) (ppm adi.) ungicides
WP
9 45 5.2 10.3 223
Table 17 . Synergism factor (SF) after artificial rain stress for various mixture of
TPN and Metalaxyl against late blight in tomato
Fungicides
FL
WP
Ratios 0.5 pm 1.0 pm 1.5 pm 5.0 npn
Table 18. Theoretical EC90 for various mixture of TPN and Oxadixyl against late blight in tomato (ppm a.i.)
Fungicides FL
WP
Ratios osm | 1.0 pm 1.5 pm 5.0 pm mwa] ws] mel as] wwe] ws] mi] de]
Table 19. Fungicidal activity after artificial rain stress for various mixture of
TPN and Oxadixyl against late blight in tomato (observed EC20) ungicides FL
WP
0.5 pm 1.0 pm 1.5 pm 5.0 pm
Ratios
Cee ee mma eee se] ei] ms
Table 20. Synergism factor (SF) after artificial rain stress for various mixture of
TPN and Oxadixyl against late blight in tomato (ppm a.i.)
Fungicides FL
WP
Ratios 0.5 pm 1.0 pm 1.5 pm 5.0 ym :
The test results presented hereinabove demonstrate that the composition proposed in this invention presents an excellent fungicidal effect and an ample synergistric effect.
Claims (9)
1. A flowable fungicidal composition comprising the active ingredients. a) a compound of the formula [1] 0 CH, X, wen {1} Z CH, x wherein R is pethoxymethyl, Z is »—oxo-1,3-oxazolidin=3-¥1s \- (methoxycarbonyl) ethyl: Xx, is H and x, is H } and b) totrachlorisophthalonitrile: and a surfactant in water, wherein the weight ratio of the compound of formula I: tetrachloroisophthalonitrile is within the range of from 1:2 to 1:15, and wherein the solid components have a particle size in the range of from
0.5 to 5 micron at the 50 % volume accumulation point.
2. The composition of Claim 1. wherein the weight ratio of compound of foumula I: cotraisophthalonitrile is within the range of from 1:3 to 1:13
' . Cote %, The commosition of £laim 1, wherein the weieht ratio of compound of formula I: tetraisophthalonitrile is within the ranre of from 1:4 to 1:12.
4, The composition of Claim 1, wherein the weight ratio of comround of formula 1: tetraisophthelonitrile is within the ranee of from 1:4 to 1:11,
5. The composition of Claim 1, wherein the solid comnon~nts have a varticle size in the range of from 0.8 to 2.5 micron at the 50% volume accumulation point.
6. The comnosition of Claim 1, wherein the solid components have a rarticle size in the range of from 0.8 to
1.8 micron at the 50% volume accumulation point. 7, The composition of Claim 2, wherein the solid components have a narticle size in the range of from 0.8 to 2.5 micron at the 50% volune accumulation point.
8. The composition of Claim 2, wherein the solid componrnts have a particle size in the range of from 0.8 to 1.8 micron at the 50% volune accumulation point.
9. The composition of Claim 1, comprising from 1%
. to 7% bv weirht of active ingredients.
Abstract of the Disclosure The invention provides a flowable composition comprising tetrachloroisophthalonitrile (TPN) and a compound of formula [I] i CH, X, R-C-N 9% [1} Z CH, xy wherein R, Z, Xx, and X, are as defined in the description, in a weight ratio range of compound of formula I: TPN of from 1:2 to 1:15, and wherein the solid compounds have a particle size in the range of from 0.5 to 5.0 um at the 50 % volume accumulation point. :
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP63060486A JP2568099B2 (en) | 1988-03-16 | 1988-03-16 | Disinfectant composition |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PH26831A true PH26831A (en) | 1992-11-05 |
Family
ID=13143656
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PH38334A PH26831A (en) | 1988-03-16 | 1989-03-15 | Fungicidal composition |
Country Status (9)
| Country | Link |
|---|---|
| JP (1) | JP2568099B2 (en) |
| KR (1) | KR920002221B1 (en) |
| DE (1) | DE3908460C2 (en) |
| ES (1) | ES2013120A6 (en) |
| FR (1) | FR2628604B1 (en) |
| GB (1) | GB2216798B (en) |
| IT (1) | IT1232821B (en) |
| NL (1) | NL194985C (en) |
| PH (1) | PH26831A (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5496845A (en) * | 1994-05-25 | 1996-03-05 | American Cyanamid Co. | Suspension concentrate compositions of arylpyrrole insecticidal and acaricidal agents |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1114941B (en) * | 1977-12-27 | 1986-02-03 | Sipcam Spa | FUMERO - PATENT CONSULTING STUDY S.N.C. VIA S.AGNESE, 12 MILAN |
| IT1096345B (en) * | 1978-05-26 | 1985-08-26 | Sipcam | FUNGICIDE COMPOUND |
-
1988
- 1988-03-16 JP JP63060486A patent/JP2568099B2/en not_active Expired - Fee Related
-
1989
- 1989-03-13 FR FR8903368A patent/FR2628604B1/fr not_active Expired - Fee Related
- 1989-03-13 KR KR1019890003026A patent/KR920002221B1/en not_active IP Right Cessation
- 1989-03-13 GB GB8905713A patent/GB2216798B/en not_active Expired - Lifetime
- 1989-03-14 IT IT8947739A patent/IT1232821B/en active
- 1989-03-15 PH PH38334A patent/PH26831A/en unknown
- 1989-03-15 DE DE3908460A patent/DE3908460C2/en not_active Expired - Fee Related
- 1989-03-16 NL NL8900641A patent/NL194985C/en not_active IP Right Cessation
- 1989-03-16 ES ES8900968A patent/ES2013120A6/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| GB2216798A (en) | 1989-10-18 |
| NL8900641A (en) | 1989-10-16 |
| KR890013986A (en) | 1989-10-21 |
| GB2216798B (en) | 1991-10-02 |
| NL194985C (en) | 2003-10-03 |
| DE3908460C2 (en) | 2003-12-04 |
| IT1232821B (en) | 1992-03-05 |
| JP2568099B2 (en) | 1996-12-25 |
| JPH01238504A (en) | 1989-09-22 |
| DE3908460A1 (en) | 1989-09-28 |
| FR2628604B1 (en) | 1996-05-31 |
| KR920002221B1 (en) | 1992-03-20 |
| FR2628604A1 (en) | 1989-09-22 |
| GB8905713D0 (en) | 1989-04-26 |
| ES2013120A6 (en) | 1990-04-16 |
| IT8947739A0 (en) | 1989-03-14 |
| NL194985B (en) | 2003-06-02 |
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