CA2022508A1 - Agricultural or horticeeltural fungicide - Google Patents

Abstract

Abstract An agricultural or horticultural fungicide comprising a compound of the following formula (I), as an active ingredient:
(I)

Description

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Our Ref.: HC-54 AGRICU~TURAL OR HORTICEELTURAL FUNGICIDE
The present invention relates to an agricultural or horticultural fungicide.
In modern agriculture, high productivity is secured by means o~ fertilizers, agricultural chemicals and various agricultural materials~ On the other hand, emergence of chemical-resis;tant bacteria due t~
continuous application of agricultural chemicals and diseases due to repeated cultivation of the same crop plants in a locally concentrated fashion, have now become serlous problems. Under these circumstances, it is strongly desired to develop highly safe agricultural and horticultural agents, and the present invention provides a means to meet such a desire.
The present invention prov.ides an agricul~ural or horticultural fungicide compr.ising a compound of the following formula (I), as an activs ingredient:

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CH ce H

3 ~

c e ~ C-CH2CH2CH3 (I) ~\~

Now, the present invention will be described in further detail with reference to the preferred embodiments.
The compound of the formula (I) can be prepared by reacting a compound of the rollowing formula (II) with imidazole in a suitable solvent.
CH3 ce ce ~ CH-CH2CH2CH3 (II) . .
wherein X is a chlorine atom or a bromine atom.
The compound of the formula (II) can be prepared by a known reaction of the corresponding phenylalkylmethanol with e.g. thionyl chloride~
The main properties of the compound of the formula (I) are as follows:
Nature: oil IR (cm~l): 3098, 1584, 939, 912 For the application of the compound oE the present invention, it may be formulated into a wettable powder, an emulsiEiable concentrate, a granule, a dust, etc. by means of a solid carrier or a liquid carrier in accordance with a usual agricultural formulation method.

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2~22~8 As the liquid diluent or carrier, an aromatic hydrocarbon such as xylene, a chlorinated aromatic hydrocarbon such as chloroben~ene, a~ alcohol such as butanol, a ketone such as methyl isobutyl ketone or isophorone, or a polar solvent such as dimethyl formamide or dimethyl sulfoxide, and water, are preferably employed.
As the solid diluent or carrier, a mineral powder such as kaolin, talc, clay, montmorillonite or diatomaceous earth, or a synthetic or natural polymer ; compound such as a polyalkylene glycol ester gum, may be employed.
Preferred emulsifiers include, for example, non-ionic emulsifiers such as polyoxyethyiene fatty acid esters and polyoxyethylene alkylethers, and anionic emulsifiers such as alkylaryl sulfonates, aryl sulfonates and alkyl , sulfonates. Preferred dispersants includer for example, lignin and methyl cellulose.
Extenders such as carboxymethyl cellulose as well as powdery, granular or grating natural and synthetic polymers such as gum ~rabic, polyvinyl alcohol and polyvinyl acetate ! may be used Eor the formulatlons.
The formulations usually contain from 0.1 to 95% by weight, preferably from 0.5 to 50~ by weight, of the active compound.
The fungicide of the present invention is applied in ~ ~ a sufficient amount so that the active compound provides `:~

.. . , -adequate effects. The dose of the active compound is within a range of from 50 to 2,000 g/ha, usually from 50 to 1,000 g/ha.
Now, the present invention will be described in further detail with reEerence to Examples. In these Examples, "parts" means "parts by weight".
Example 1 Compound of the formula (I) 10 parts Clay 80 parts Polyoxyalkylphenyl sulEate 5 parts White carbon (fine silica) 5 parts The above materials were pulverized and mixed to obtain a wettable powder.
. Example 2 Compound of the formula (I) ~0 parts .
;; Xylene 70 parts Sorpol 800 A (trademark of Toho Chemical Co., Ltd. ?
for a surfactant comprising a polyoxyethylene sorbi~an alkylate, a polyoxyethylene alkylphenol polymer and calcium sulfonate, manufactured by Toho Chemical Co., Ltd.) 10 parts The above materials were mixed to obtain an emulsifiable concentrate.
Example 3 25 Compound of the ~ormula (I) 10 parts Lignin 2 parts Bentonite 88 parts .

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The above materials were mixed and kneaded with water, followed by granulatioll and drying to obtain a granule.
Example 4 Compound of the ~ormula(I) 20 parts Isophorone l0 parts Xylene 20 parts Orthochlorotoluene 35 parts Sorpol 900 ~ (trade mark of Toho Chemical Co., Ltd.
for a surfactant comprising a polyoxyethylene sorbitan alkylate/ a polyoxyethylene alkylphenol polymer, a polyoxyethylene alkylallylether, and calcium sulfonate, manufactured by Toho Chemical CoO, Ltd.) 7.5 parts Sorpol 90~ B (trade mark of Toho Chemical Co., Ltd.
for a surfactant comprising a polyoxyethylene sorbitan alkylate, a po1yoxyethylene alkylphenol polymer, a polyoxyethylene alkylaIlylether, and calcium sulfonate, manuactured by Toho Chemical Co., Ltd.) 7.5 parts The above materials were mixed to obtain an emulsifiable concentrate.
Now, mycelium growth inhibitory effects and disease protectant activity of the compounds of the present invention against typical fungi will be described with respect to Test Examples.

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Test Example l Test for mycelium qrowth inhibitory effects on a Petri dish A potato-dextrose agar oulture medium (PDA medium) and a dimethyl sulfoxide solution of the compound were mixed to a concentration of 100 ppm, and the mixture was poured into a Petri dish to form a plate culture medium.
Onto this culture medium, two disc specimens with a diameter of 4 mm of each of PYthium qraminicola, Fusarium oxysporum and Rhiæoctonia solani, which were preliminarily cultured on PDA culture media, were "; placed, and cultured at 25C for two days in the case oE
PYthium qraminicola, five days in the case of Fusarium oxysporum and for three days in the case of Rhizoctonia ~ 15 solani. Then, the diameter of each colony was measured :, and compared with the colony diameter on a non-treated medium, and the growth inhibition was calculated in accordance with the following equation.
A ~ B
Growth inhibition ~%) = - x 100 A
A: Colony diameter on the non-treated medium B: Colony diameter on the treated medium The average values of the results are shown in Table 1.

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Table l _ ~
Fungi Pythium Fusarium Rhizoctania qraminicola oxysporum olani ~ ~ . _ ~ __ Growth Inhibition by Compound of the formula (I) __~_ _ ___ n _ _ __ _ -- _ _ _ _ ____ _ __ _ _ _____ Test Example 2 Test for protectant activity aqainst downy mildew of cucumber Cucumber (varietyO Kashu No.l) was cultured in a porous porcelain pot having a diameter of 9 cm, and when it reached a 3-leaf stage, the wettble powde~ of the test compound ormulated in accordance with Example l was diluted to have a concentration of lO0 ppm, and 20 me of .
lS the solution of the test compound was sprayed by means of a spray gun. Three cucumber plants were treated with each test compound.
After drying them 24 hours, a suspension of spores (2 x 105 spores/me) of Pseudoveronosporea cubensis cau.sing downy mildew of cucumber, was sprayed and inoculated to each plant. After the inoculation, the cucumber plants were cultured at 20C under a moisture-saturated condition for 12 hours and then at 20C under a relative humidity of from 70 to ~o% for 6 days. Seven days after the in~culation, the proportions oE lesion on the first leaf and the second leaf were examined, and the control value were determined by the following formula to obtain ,:

- B ~
the results as shown in Table 2~ As a comparative compound, Compound A as identified in Table 3 was used.
C - ~
Control value = x 100 :~ 5 C: Proportion of lesion at the non-treated section D: Proportion of lesion at the treated section ,, - Table ~
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: Comp~und C~tr~ =
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Table 3 Symbols for St~ct~e~ .e - - p~a :~v~
comparat.ive compounds compounds ~

CE ~ -e ~:~ ~
~ _ , . -- -ce~ O ~ nC6~13 . ~
) i~C~

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Ta~le 3 (continued) Symbols for Structures of comparative Common names comparative compounds r IJ: l .. . . . .

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Test Example 3 Test for protectant activit~ aqainst powdery mildew of wheat Wheat (variety: Norin No~ 61) was cultured in a pot having a diameter oE 9 cm, and when it reached a 2-leaf stage, the emulsifiable concentrate of the test compound formulated in accordance with Example 4 was diluted to . have a concentration of 100 ppm, and 20 m~ of the : solution of the test compound was sprayed by means of a spray gun. With respect to each test compound, treatment was conducted in two series each consisting of 13 wheat ~` plants per section.
After drying the plants for 24 hours, conidia of ~:~ Eryshiphe qraminis causing powdery mildew of wheat, were ` 15 sprayed and inoculated to each wheat plant. After this inoculation, the wheat plants were cultured at 20C in a dark place under a moisture-saturated condition for 12 hours and then at 20C for 6 days. Seven days after inoculation, the portions of lesion on the first lea and the second leaf were examined, and the control value was obtained in the same manner as in Test Example 2 to .~ obtain the results as shown in Table 4. As a comparative compound, Compound B as identified in Table 3 was used.

Table 4 25 _. _ Compound Control value . ~ __ ._ _ .
~ , ~3, 10,, , .~

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Test Example 4 Test for protectant activitY aqainst qlume-blotch of -wheat Wheat (variety: Norin No. 61) was cultured in a pot ; 5 having a diameter oE 9 cm, and when it reached a 2~1eaf stage, the emulsifiable concentrate of the test compound formulated in accordance with Example 4 was diluted to have a concentration of lO0 ppm, and 20 me of the solution of the test compound was sprayed by means of a spray gun. With respect to each test compound, treatment was conducted in two series each consisting of 13 wheat plants per section.
After drying the plants for 24 hours, a suspension of spores ~106 spores/me~ of Lepto-sphaeria nodorum causing glume-blotch of wheat, was sprayed and inoculated to each ::~
wheat plant. After this inoculation, the wheat plants were cultured at 18C un~er a relative humidity of 90%
or lO days. lO days after the inoculation, the proportions of lesion on the ~irst leaf and the second leaf were examined, and the control value was obtained in : .
the same manner as in Test Example ~ to obtain the results as shown in Table 5. As a comparative compound, Compound C as identi~ied in Table 3 was used.

Table 5 Compound Control value __ . . .
I lO0 C 40 =
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Test Example 5 Test for eradicant effects aqain~t powdery mi]dew of wheat Wheat (variety: Norin No. 61) was cultured in a pot havin~ a diameter of 9 cm, and when it reached a 2-leaf stage, conidia of Eryshiphe qraminis causing powdery mildew of wheat were sprayed and inoculated. ~fter this inoculation, the wheat plants were cultured at 20C in a dark place under a moisture-saturated condition for 12 hours. Then, the emulsifiable concentrate of the test :
compound formulated in accordance with Example 4 was diluted to have a concentration oE 1 ppm, and 20 me of ~; this solution was sprayed by means of a spray gun. Wi-th respect to each test compound, treatment was conducted in lS two serles each consisting of 13 wheat plants per section.
After the application of the compound, the plants were cultured at 20C for 6 days. Seven days after the inoculation, the portions of lesion on the first leaf and the second leaf were examined, and the control value was obtained in the same manner as in Test Example 2 to obtain the results as shown in Table 6. ~g a comparative compound, Compound D as identified in rrable 3 was used~
Table 6 _ _ Compound Control value _ . .. _ I

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As described in the foregoing, the present invention exhibits fungicidal activities against various filamental fungi and shows protectant activity against diseases of crop plants, and thus it presents an effective means for improving the yield of harvest without phytotoxicity.

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Claims

THE EMBODIMENTS OF THE INVENTION IN WHICH AN EXCLUSIVE
PROPERTY OR PRIVILEGE IS CLAIMED ARE DEFINED AS FOLLOWS:

1. An agricultural or horticultural fungicide comprising a compound of the following formula (I), as an active ingredient:

(I)