JPS60136565A - Acetal compound, its production and agricultural and horticultural germicide containing the same - Google Patents

Abstract

NEW MATERIAL:An acetal compound expressed by formula I (X is halogen, CF3 or alkyl; Y is halogen, alkyl or alkyloxy; m and n are integers 0-2, provided that X or Y may be the same or different when m or n is 2; R1 and R2 are independently saturated lower carbon chain or unsaturated lower carbon chain or R1 and R2 link to form alkylene or substituted alkylene). EXAMPLE:2-(4-Chlorobenzoyl)-isonicotinanilide diethyl acetal. USE:An agricultural and horticultural germicide capable of exhibiting improved action on blights of cultivated useful crops and high safety for humans, animals and fishes. PREPARATION:A benzophenone derivative expressed by formula II is reacted with a halogenating agent and then the corresponding alcohol to afford the aimed compound expressed by formula I .

Description

Detailed Description of the Invention The present invention is based on the general formula (1) (wherein, X represents a halogen atom, a trifluoromethyl group or a lower alkyl group, and Y represents a halogen atom, a lower alkyl group or a lower alkyloxy group). Indicates an integer between 0 and 2.

When 倶 or 外 is 2, X or Y may be the same or different, respectively. R1 and R2 each independently represent a saturated lower carbon chain group or an unsaturated lower carbon chain group, or combine to form a cyclic alkylene-OH20H20H
Indicates a 20H2- group, etc. ) acetal compounds, their production method, and one of these acetal compounds
The present invention relates to an agricultural and horticultural fungicide characterized by containing one species or two or more species as active ingredients.

Many synthetic organic compounds and antibiotics with bactericidal properties have already been discovered, and many substances have been developed as fungicides for agriculture and horticulture.

However, in recent years, the emergence of resistant bacteria and environmental pollution due to mass spraying have become problems.

Also, recently, many inventions related to so-called azole compounds as agricultural and horticultural fungicides have been announced.

For example, JP-A-56-152446, JP-A-57-168
70, JP-A-57-48982, JP-A-57-1205
79, Japanese Unexamined Patent Publication No. 57-126479.

However, these compounds often have plant growth inhibitory and herbicidal effects, and have the drawback that they cannot necessarily be said to be safe to use.

In order to compensate for these shortcomings, the present inventors have
The present invention was achieved through intensive efforts to develop a drug that has a novel skeleton and is highly effective even in small amounts.

The compound of the present invention represented by the general formula (1) is a novel compound that exhibits excellent effects against diseases of useful cultivated crops, is highly safe for humans, livestock, and fish, and is effective against crops. It does not show any adverse effects on

The compound of the present invention represented by general formula (1) can be widely applied to farms for both prevention and treatment. In particular, it shows excellent efficacy against powdery mildew, rust, etc. of useful plants.

In the production of the compound of the present invention represented by general formula (1), methods already known (for example, JP-A-55-139306) may be used.
Benzophenone derivative (II) (wherein the formula X , Y
, m and bean paste have the same meanings as above. ) with a suitable halogenating agent such as thionyl chloride, thionyl bromide, phosphorous pentachloride, etc., using no solvent or an inert solvent such as methylene chloride, chloroform, benzene, toluene, etc., and the resulting reaction product. By reacting with a corresponding alcohol, the desired compound of the present invention [1] can be obtained easily and in good yield. In this reaction, a suitable deoxidizer such as triethylamine, pyridine, N,N-dialkylaniline, sodium hydroxide is used.

By using potassium, sodium alkoxide, etc., the reaction proceeds more smoothly. For this reaction, inert solvents such as tetrahydrofuran, diisopropyl ether, dioxane, etc. may be used.

Among the compounds of the present invention [■] thus obtained, some compounds have asymmetric carbon atoms in their structures. Therefore, it is clear that these compounds exist as different stereochemically optical isomers. Namely, R.
' are combined to form a cyclic structure, a so-called dioxolane skeleton, and when the dioxolane ring has an alkyl group at the 4-position, the carbon atoms at the 4- and 2-positions are asymmetric.

Stereochemical optical isomers of the compound [1] of the present invention can be resolved and isolated by known methods.

Isomers are included within the scope of this invention.

Next, a manufacturing example will be given and explained.

Production Example 1゜2-(4-chlorobenzoyl)-isonicotine anilide diethylacetal (compound number 9) 2-(4-chlorobenzoyl)-isonicotine anilide 112 was added to thionyl chloride 100x/4 hours rIIj
I played M. Thionyl chloride was completely distilled off under reduced pressure, and 100 ml of ethyl alcohol was added to the resulting reaction product under water cooling.
Furthermore, 15 m/ml of triethylamine was slowly added dropwise. After the completion of the dropwise addition, the reaction mixture was further stirred at room temperature for 2 hours, and then the reaction mixture was distilled under reduced pressure. Water was added to the resulting reaction mixture, and then extracted with ethyl acetate. The obtained ethyl acetate layer was dried with magnesium sulfate, the ethyl acetate was distilled off under reduced pressure, and the remaining reaction product was diluted with vinegar.
When recrystallized from a mixture of methyl ester and n-hexane, the desired 2-(4-rebenzoyl)-isonicotine anilide diethyl acetal is obtained at 11,0? (
Yield 8o%) was obtained. Melting point 98-99°C.

Elemental analysis value: 0zsH230jlr4203 molecular weight 4
! 0.89OHN Calculated value (to) 67.23 5.64 6.82 Experimental value (:d 67.09 5.72 6.70 Production example λ 2-(4-ritIobenzoyl)-isonicotinanilide dimethyl acetal ( Compound No. 4) Under the same conditions as Production Example 1, using methyl alcohol instead of ethyl alcohol, 2-(4-ri0pbenzoyl)
-Isonicotine anilide dimethyl acetal at 10.
2f (yield 8o%) was obtained.

Melting point: 137-138°C Elemental analysis: 0ztHt90j! N2O3 molecule m38
2.24OHN Calculated value (total) 65.99 5.01 7.33 Experimental value % 66.05 5.08 7.23 Production example 3゜2-(4-ri-tetralobenzoyl)-isonicotine anilide - Probil acetal (Compound No. 42) Under the same conditions as in Production Example 1, using ethyl alcohol instead.
n-propyl alcohol t [uN, 2-(4-chlorobenzoyl)-isonicotine anilide exo-probyl acetal 12.4 PC yield "4<85%)" was obtained. Melting point 140-141°C Elemental analysis Value: (325H2701N203 molecular weight 43
B, 95OHN Calculated value (to) 68.41 6.20 6.38 Experimental value (to) 68.2B 6.24 6.31 Production example 4゜2-(4-chlorobenzoyl)-isonicotine anilide - Butyl acetal (Compound No. 41) Under the same conditions as Production Example 1, using exo-butyl alcohol instead of ethyl alcohol, the obtained product was separated and purified by column chromatography using silica gel.
-(4-ri-p-lobenzoyl)-isonicotine anilide
Di-butyl acetal as an oily substance 12.5
ft (yield: 80%).

NMR data are shown in the attached table.

Elemental analysis value: 027H3101N203 molecular weight 467
．． 00OHN Calculated value (To) 69.44 6.69 6.00 Experimental value (Foundation) 69.35 6.74 5.89 Production example 5゜2-(4-Methylbenzoyl)-isonicotinanilide diethylacetal (compound number 25) Using the same conditions as in Production Example 1, using 10.5r of 2-(4-methylbenzoyl)-isonicotine anilide instead of 2-(4-chlorobenzoyl)-isonicotine anilide, and producing 2-(4- Methylbenzoyl)-isonicotine anilide diethylacetal 11.7 f (yield 90%)
) was obtained.

Melting point 95-96℃ Elemental analysis value: 024H26N203 molecules ff1390
．． 48OHN Calculated value (Foundation) 73.82 6.71 7.17 Experimental value (To) 73.77 6.78 7.21 Production example 6゜2-(4-Methylbenzoyl)-isonicotine anilide Di-propyl alcohol (Compound No. 33) In Production Example 5, exo-propyl alcohol was used instead of ethyl alcohol, and 2-(4-methylbenzoyl)
- Isonicotine anilide outside - Probyl acetal 1
1.9 f (85% yield) was obtained. Melting point 120-12
1°C Elemental analysis value: 026) (3ON203 molecular weight 418.
54Q HN Calculated value (6) 74.61 7.23 6.69 Experimental value (to) 74.47 7.30 6.61 Production example 7゜4-chloro-2-benzoyl-isonicotine anilide
Production of diethylacetal (Compound No. 7) According to Production Example 1, 1 L 2 f of 4-chloro-2-benzoylisonicotine anilide was reacted in the same manner, and N,N-diethylaniline 15 was added instead of triethylamine.
10.3 f of the desired 4-chloro-2-benzoylisonicotine anilide diethyl acetal using m/.
(yield 75%).

Melting point 133-134℃ Elemental analysis value: 023H2301N203 Molecular weight 410
．． 89OHN Calculated value (foundation) 67.23 5.64 6.82 Experimental value (6) 67.35 5.59 6.91 Production example 8゜4-chloro-2-(4-chlorobenzoyl)-isonicotinanilide diethyl Acetal (compound number 13)
Preparation of 4-E2-2-(4-chlorobenzoyl)-isonicotine anilide 12.4f was reacted according to Production Example 1, using pyridine 10 in place of triethylamine.

Thus, 4-chloro-2-(4-ri p-lobenzoyl)-
Isonicotine anilide diethyl acetal 11.1
? (yield 75%). Melting point: 123-124℃ Elemental analysis: 023H220j12N203 Molecular pattern 4
45.34OHN・ Calculated value (to) 62.83 4.98 6.29 Experimental value (to) 59.97 5.07 6.24 Production example 9゜2-benzoyl-isonicotinanilide dimethyl acetal (compound number 1) Production of 2-penzoyl-isonicotine aniline) '10F was added to 200 m/m of benzene, heated to reflux with stirring, 20 d of thionyl chloride was gradually added, and the mixture was heated and stirred for 4 hours. After cooling to room temperature, benzene and excess thionyl chloride were completely distilled off under reduced pressure. The previously obtained mixture was added to a solution prepared by dissolving 3 tons of sodium hydroxide in 100 ml of methyl alcohol using a stirring stopper, and stirring was continued for an additional 2 hours at room temperature. After distilling off the methyl alcohol under reduced pressure, add water and finish with ethyl acetate.

Extracted with ester. The ethyl acetate layer was separated and dried over anhydrous sodium sulfate. The ethyl acetate was distilled under reduced pressure and recrystallized from a mixed solvent of ethyl acetate and n-hexane to obtain 2-benzoylisonicotine anilide dimethyl acetal (7.5fC yield: 65%).

Melting point 123-124℃ Elemental analysis value 021H2ON203 molecule m348.4
0OHN Calculated value (to) 72.40 5.79 8.04 Experimental value (to) 72.50 5.70 8.11 Manufacturing example i o
.

Production of 2-benzoyl-isonicotine anilide diethyl acetal (compound number 6) According to the method of Production Example 9,
Using ethyl alcohol instead of methyl alcohol and 4f potassium instead of sodium hydroxide, the desired 2-benzoylisonicotine anilide diethyl acetal &8
9t (yield 70%) was obtained. Melting point 114-115℃ Elemental analysis value: 0zsHz4Nz0s Molecular weight 376.45
OUN Calculated value (2) 73.38 6.43 7.44 Experimental value (to) 73.30 6.51 7.39 Production example 1L 2-(4-chlorobenzoyl)-4-7/I/'Oloiso Production of Nicotine Anilide Diethylacetal (Compound No. 16) 2-(4-chlorobenzoyl)-4-fluoro-
Isonicotine anilide 12S' was added, and the mixture was refluxed for 2 hours while stirring with heating. After cooling, a solvent was gradually added under reduced pressure, and the mixture was allowed to react at room temperature for 2 hours. After the reaction was completed, ethyl alcohol was distilled off under reduced pressure, water was added to the reaction mixture, and the mixture was extracted with ethyl acetate.

After drying the acetate ethyl ester layer over anhydrous sodium sulfate, the acetate ethyl ester was distilled under reduced pressure, and the obtained product was recrystallized from an ethyl nitrite acetate n-hexane mixed solvent to yield 2-(4-chlorobenzoyl). -4-Fluoro-isonicotine anilide diethylacetal 10.7
F (yield 75%) was obtained. Melting point 96-97℃ Elemental analysis value: 023H22QJlFN203 Molecular weight 4
28.71OHN Calculated value (goods) 6444 5.13 6.53 Experimental value (
) 64.27 5.00 6.61 Production Example 12゜2-(3,4-dichlorobenzoyl)-isonicotine anilide Diethylacetal (Compound No. 20) 2-(3,4-dichlorobenzoyl)-isonicotine anilide 12.4f and reacted in the same manner as in Production Example 11, using 2.0 t of metallic sodium instead of potassium, to obtain 2-(3,4-dichlorobenzoyl)-isonicotine anilide diethyl acetal 119F (yield). rate 80
χ) was obtained.

Melting point 113-114℃ Elemental analysis value: 0z3Hz0jhN203 molecular weight 44
5.340 HN Ml' Calculated value (goods) 62.03 4,98 6.29 Experimental value (to) 59.90 5.05 6.34 Production example 1
3゜4-Bromo-2-benzoyl-isonicotine anilide
Preparation of dimethyl acetal (compound number 3) 4-promo 2-benzoyl isonicotine anilide 1
Using 2.7 f, 4-bromo 2
-Benzoylisonicotine anilide dimethyl acetal 11.45' (113180%) was obtained. Melting point 189
~190℃ Original cumulative analysis value: 021H1gBrNz03 molecule ff14
27.29OHN Calculated value (to) 59.03 4.48 6.56 Experimental value (to) 59.11 4.56 6.644-10Rho 2-(4-chlorobenzoyl)-6-methyl-isonicotinanilide Diethylacetal (compound number 59)
Production of 4-chloro-2-(4-recirculated benzoyl)-6
-Methyl-isonicotine anilide 12.8 f was treated according to the method of Production Example 1 to obtain 4-chloro-2-(4-10
lobenzoyl)-6-methyl-isonicotine anilide
Diethyl acetal 13.0 F (yield 85%) was obtained. Melting point 134-135℃ Elemental analysis value: 0z4H24
0JlzN203 molecule 1459.37OHN Calculated value (6) 62.75 5.27 6.10 Experimental value (to) 62.61 5.34 5.94 Production example 15°5-rihalow2- (4-chlorobenzoyl) -6-Methyl-isonicotine anilide Production of diethyl acetal (compound number 66) 5-chloro112-2-(4-ri0
p-benzoyl)-6-methyl-isonicotine anilide 1
2.8 f was treated in the same manner as in Production Example 1 to obtain 5-chloro-2-(4-chlorobenzoyl)-6-methyl-isonicotine anilide diethylacetal 12.2 yen (yield 80%). Ta. Melting point 156-157℃ Elemental analysis value:
o24) (24c”2N2o3 molecular weight 459.370
HN Calculated value (6) 7461 7.23 6.69 Experimental value) 74.49 7.31 6.60 Production example 16゜2-(4-ri00benzoyl)-1'/Nicotine anilide Ethylene acetal (Compound number 73) Production of 2-(4-chloro0/<nzoyl)-isonicotine anilide 111 was reacted with thionyl chloride according to Production Example 1, and 150 d of tetrahydrofuran and 30 d of ethylene glycol were added to the product obtained. The mixture was stirred for about 20 minutes while cooling with water. 25 d of triethylamine was added dropwise to this bath liquid, and after the addition was completed, the mixture was stirred for 1 hour, and stirred for an additional 4 hours at room temperature. The obtained reaction mixture was treated according to Production Example 1, and 2-
((4-chlorobenzoyl)-isonicotine anilide
10.2f of ethylene acetal (yield: 80%) was obtained.

Melting point 102~'103℃ Elemental analysis value: 021H170J! N2O3 molecule ff1
380.82OH,N Calculated value (6) 66.23 4.50 7.36 Experimental value (g) 66.28 4.61 7.27 Production example 17゜2-(4-chlorobenzoyl)-isonicotine anilide pull Preparation of pyrene acetal (Compound No. 76) Using 2-(4-chlorobenzoyl)-isonicotine anilide 111 and using propylene glycol instead of ethylene glycol in Production Example 16, the same treatment was carried out.
10.5f (yield: 80%) of 4-chlorobenzoyl)-isonicotine anilide propylene acetal was obtained.

Melting point: 125-126°C Elemental analysis: 022H190jlN203 Molecular weight: 39
4.8 ri0 HN Calculated value ■ 66.92 4.85 7.09 Experimental value (to) 67.04 4.81 7.15 Compounds of the present invention obtained in the same manner are shown in Table 1. However, the compounds shown in Table 1 do not limit the present invention.

In addition, the compound numbers in Table 1 are production examples and test examples.

This also applies to formulation examples.

In Table 1, the positional representation (numbering) of substituents X and Y is as follows.

In addition, in the substituents in the table, Me is a methyl group Et is an ethyl group Pr is an n-propyl group Bu is an n-butyl group All is an allyl group *1): NMR (,0DO1a) δCP) 3.1
8 (6H, 8), 7.0~7-5 (7H, missed)
, 7.85 (IH, d), 8.32 (IH, d).

8.75 C2He bd) e 9.50 (lH#
bs) Rice 2): NMR (0DOIts) a(
P) 3.18 (6HeS) -6,91~7.7
2 (8H, tn), 8.33 (IH, d, J depth 9.6
Hz, 4.8Hz).

8.77 (2H, m), 9.41 (IH, 5) 43)
: NMR(0DOA3)δ(p)1.19(6H,
t), 3.37 (4H.

q), 6.79-7.54 (8H, w),
7.93-8.74 (4H, m), 9.66 (IH,
8) 14): NMR (CD0I3) δ (llP+Il) 1
．． 19 (6H, t), 3.37 (4H.

q), 7.06~7.54C8H,rn), 7.93~
8.74(]Kaiday,=o,,,.

4 He tn ) 9.53 (1H-8) 45):
NMIL (ODO13) δ (yellow) 0.72-0.96
(6H, m), 1.28-1.76 (4H, m)
, 3.50-2.90 (4H, m), 6-70-8.7
6 (12H, m) *-6): NMR (CD0I3) δ (FF) 2.2
．． 2(3H,S), 3.15(6J(.

S), 6.86-7.37 (6H, Jou), 7.45-7
．． 55 (2H, m) p7.70-7.95 (IH, ac
), 8.34-8.50 (IH, m), 8.70=8
．． 80 (2H, m), 9.76 (IH, bs) 7)
:NMR(CD0I3)δ(P)0.76-0.96(
6H, snow), 120-1.72 (8H, regret), 3.18
~3.36 (4H, bath).

7.02-7.53 (8H, Jo), 7.75-8.80
(IH, always).

8.25-8.36 (IH, m), 8.72-8.82
(I love 2H).

9.50 (IH, bs) Rice 8): NMR (ODOjL3) δ (pH 11)
0.71-0.95 (6H, fi), 1.28-176
(4Hr tn ), 2.23 (3H, 8) 1
3.50-2.90 (4H, m), 6.91-8.73
(IIH, m) 19.40 (LH, S) 9): NMR (ODOJ23) δ (JIP) 0.9
7-1.30 (9H, m), 2.51 (2H, q)
, 3.36 (4H, q), 6.86-8.75 ((12
H, Shin), 9.60 (IH, 8) rice 10): NMR (O
DOλ3)δ(14!11)0.96(6H,t), 1
．． 53 (4H.

Raku), 2.20 (3H, 8), 3.15 (4H, t),
6.79-8.70 (IIH, 倶), 8.41 (IH,
S) Rice 11): NMR (CDOA3) δ (lpl) 0.
80-1.12 (3H, m), 1.32-2-00 (
2H+tn) v 3-40~4.42 (3H,
tn).

7.00-7.75 (9H, m), 8.21-8.41
(LH.

m), 8.60-8.72 (2H, m), 9.68 (I
H, bs) This NMR clearly shows that it is a mixture of isomers.

Rice 12) 13): Compound number 97.98 is an isomer.

Since the compound of the present invention thus obtained has systemic transferability to plants, any treatment method such as above ground line foliage treatment, 1 seed treatment, water surface treatment or soil treatment is possible.

~Also, since the compound of the present invention does not have any adverse effect on the target useful plants, the time of use of the compound of the present invention is 1, before sowing, during the sowing period, during the seedling period, during the growing period, during the fruiting period, etc. Can be used in stages.

When actually using the compound of the present invention, it is possible to use it as it is without adding other ingredients, but it is more convenient to use it in solid or liquid form, which is used in the preparation of general agricultural chemicals. By mixing with various carriers, we can create wettable powders, emulsions, oils,
It can be manufactured into single powder tablets, flowable tablets, etc.

Furthermore, there are dispersants, diluents, emulsifiers, spreading agents, wetting agents, and adsorbents for drugs.

Auxiliary agents such as thickeners, antifoaming agents, and antifreeze agents can also be added.

The carrier herein may be either solid or liquid, or a combination thereof. Listing these examples,
Talc, clay, bentonite.

Kaolin, diatomaceous earth, calcium carbonate, wood flour, starch, gum arabic, water, alcohol, kerosene.

Examples include naphtha, xylene, cyclohexanone, methylnaatalene, benzene, acetone, dimethylformamide, glyfur ether, and N-methylpyrrolidone.

Examples of adjuvants include polyoxyethylene alkyl phenyl ether, polyoxyethylene sorbitan monooleate, ethylene oxide propylene oxide copolymer, lignin sulfonate, sorbitan ester, soaps, and sulfated oils.

Alkyl sulfate ester salts 9 Petroleum sulfonates.

Dioctylsulfosuccinate salts, alkylbenzene sulfonates, aliphatic amine salts, quaternary ammonium salts, alkylpyridinium salts.

Examples include alkylaminoethylglycine, alkyldimethylhetaine, polyglycol sulfate, alkylamine sulfonic acid, isopropyl phosphate, carboxymethyl cellulose, polyvinyl alcohol, hydroxypropyl cellulose, ethylene glycol, and xanthan gum.

It can also be used as an aerosol agent by mixing with a propellant such as fluorotrichtetramethane or dichlorodifluorop-methane, or as a fumigant or smoking agent by mixing with an appropriate blowing agent or combustion agent. You can also do that.

In formulating the formulation, the mixing ratio is generally 0.05 to 95%, preferably 0.1 to 80% by weight of the compound of the present invention.
%, particularly preferably 1 to 70%, and 7% as a carrier.
0-99%, optimally 0-20% as an adjuvant. Moreover, by mixing with other fungicides, herbicides, plant growth agents, pesticides, fertilizers, etc. such as insecticides and acaricides, a wider range of effects can be expected.

When actually using the compound of the present invention, the timing of use,
Weather conditions, method of use, dosage form, location of use, target disease,
It goes without saying that it should be selected appropriately depending on the target crop, etc., but the concentration used is generally 0.5 to 1000 pplQ, preferably 3 to 500 pl! 11, and the dosage used (as the compound of the present invention) is generally 0.5 to 5 per 10 ares.
0(1', preferably 1 to 2502 per Lt107-le).

Next, the usefulness of the compound of the present invention as a horticultural fungicide will be explained using test examples.

Test Example 1 Cucumber Powdery Mildew Control Test (Preventive Effect) An unglazed needle with a diameter of 15 ounces was filled with granular horticultural soil, and 10 cucumbers (variety: Takasago) were sown. This was cultivated in a greenhouse for 10 days,
Young seedlings with expanded cotyledons were used.

The hydrating powder of the compound of the present invention obtained in Formulation Example 2 was diluted to a predetermined concentration, and 15 mg per pot was sprayed onto these seedlings. After air-drying the chemical solution, Kicumi powdery mildew M (8phae
A conidial suspension of roLheca fuliginea) was spray inoculated onto the shoots and leaves. After inoculation, the plants were cultivated for 10 days under greenhouse conditions at 23 to 26°C, and then the disease state was investigated.

The disease severity was calculated by the following method.

That is, depending on the lesion area of the investigated leaf, the following
It was classified into the severity index of I1 #213-4-s.

Based on the disease onset index thus obtained, the disease severity was calculated using the following formula, and the control value was further calculated from the comparison with the disease severity in the untreated area using the following formula.

Benomyl: 1-(Butylcarbyl)-2-benzimidazolecarbamate Methyl Variety: Takasago) 1
0 seeds were sown, cultivated in a greenhouse for 10 days, and young seedlings with fully expanded cotyledons were used for testing.

These young seedlings are infected with cucumber powdery mildew fungus (Sp haero).
thecafuliginea) and left in a greenhouse at 23-26°C for 1 day. The emulsion of the compound of the present invention obtained in Formulation Example 5 was diluted with water to a predetermined concentration. 15zxe was sprayed per pot. After air-drying, the plants were cultivated for 10 days under greenhouse conditions at 23 to 26°C, and then the disease state was investigated.

Disease state index 9 disease severity and control value are in accordance with Test Example 1.

The results are shown in Table 3.

Table 3 Test Example 3゜ Wheat powdery mildew control test (preventive effect) A clay pot with a diameter of 126 nm was filled with Arakida soil, and wheat (variety:
Norin No. 61) 15 seeds were sown. This was cultivated in a greenhouse for 12 days, and the young seedlings whose first leaves had developed were used for testing.

The emulsion of the compound of the present invention obtained by the method of Formulation Example 6 was diluted with water to a predetermined concentration and sprayed onto the seedlings at 15 me per seedling.

After air drying, wheat powdery mildew fungus (Erysiphe gra
minis) was inoculated with a conidial suspension. After inoculation, the plants were cultivated for 10 days under greenhouse conditions at 20 to 24°C, and then the disease state was investigated.

Disease severity index 2 Disease severity and control value are based on Test Example 1.

The results are shown in Table 4.

Table 4) Thiophanate methyl: 4
．． 4'-0-fxnylenebis(3-thioallophanoic acid)
Dimethyl test example 4゜Wheat powdery mildew control test (therapeutic effect) Unglazed needles with a diameter of 12 crn were filled with Arakida soil, 15 grains of wheat (variety: Norin No. 61) were sown, and cultivated in a greenhouse for 12 days until the first leaf. I tried using young seedlings that were separated.

This young seedling is infected with wheat powdery mildew fungus (Erysiphe gr.
aminis) conidial suspension was inoculated by mist, and after being left in a greenhouse at 20 to 23°C for 1 day, a wettable powder of the compound of the present invention obtained by the method of Formulation Example 2 was added with water. Dilute to the specified concentration, spray 15 m6 per pot @U, and after air drying,
After cultivating for 10 days in a greenhouse at 24°C, the disease state was investigated.

Disease severity index 2 Disease severity and control value are based on Test Example 1.

The results are shown in Table 5.

Table 5 Formulation examples are shown below. In the examples, "parts" indicate "parts by weight."

Formulation example 1 powder Compound number 4 2 parts Rishi - 98 copies glaze The above ingredients are mixed and pulverized to obtain a powder.

Formulation example 2 Hydrating agent Compound number 7 10 parts Sodium alkyl sulfonate 5 parts Formulation example 3 Hydrating agent Compound number 30 10 parts Sodium alkyl sulfonate 5 parts Rishi - 85 copies The above ingredients are mixed and pulverized to obtain a wettable powder.

Formulation example 4 Hydrating agent Compound number 74 10 parts Sodium alkyl sulfonate 5 parts Rishi - 85 years ago The above ingredients are mixed and pulverized to obtain a wettable powder.

Formulation Example 5 Emulsion Compound No. 9 5 parts Calcium alkylbenzenesulfonate 4 parts Polyoxyethylene alkyl phenyl ether 11 parts Cyclohexanone 10 parts Xylene 70 parts or more are mixed to obtain an emulsion.

Formulation Example 6 Emulsion Compound No. 44 5 parts Calcium alkylbenzenesulfonate 4 parts Polyoxyethylene alkyl phenyl ether 11 parts Cyclohexanone 10 parts Xylene 70 parts or more are mixed to obtain an emulsion.

Formulation Example 7 Emulsion Compound No. 81 5 parts Calcium alkylbenzene sulfonate 4 parts Polyoxyethylene alkyl phenyl ether 11 parts Cyclohexanone 10 parts Xylene 70 parts or more are mixed to obtain an emulsion.

Formulation Example 8 Emulsion Compound No. 16 10 parts Calcium alkylbenzenesulfonate 3 parts Polyoxyethylene alkyl phenyl ether 12 parts Dimethylformamide 10 parts Formulation Example 9 Granule Compound No. 22 2 parts Lignosulfonic acid Calcium 2 parts bentonite
30 parts Tar 66 Mix on a tool, add water and knead, then granulate and dry to obtain granules.

Formulation example 10 70 tablets Compound number 14 10 parts Ethylene glycol 5 parts Xanthan gum 0.2 parts polyoxyethylene sorbitan Monooleate 5 parts Water 79.8 parts The above is wet-pulverized to obtain a flowable agent.

Applicant: Chugai Pharmaceutical Co., Ltd. Continuation of page 1

Claims (1)

[Claims] 1. General formula (wherein, X represents a halogen atom, trifluoromethyl group, or lower alkyl group, and Y represents a halogen atom, lower alkyl group, or lower argyloxy group. Indicates an integer from 0 to 2. When the number is 2, X or Y may be the same or different. itl and R2 are each independently a saturated lower carbon chain group or an unsaturated lower carbon silver group. group, or an alkylene group or substituted alkylene group that is combined to form a ring.) Acetal compounds represented by: 2. General formula (wherein, X represents a halogen atom, trifluoromethyl group or lower alkyl group, Y represents a halogen atom, a lower alkyl group or a lower alkyloxy group. m and n
represents an integer from 0 to 2. In the case where ``Ji'' or ``Gai'' is 2, X or Y may be the same or different. ) A reaction product obtained by reacting a benzophenone derivative represented by , triph/l/oromethyl group or lower alkyl group, Y represents a halogen atom, lower alkyl group or lower alkyloxy group. 舛 and 外 represent an integer from 0 to 2. If m or dew is 2, X and Y may each be the same or different.R and 几2 each independently represent a saturated lower carbon chain group or an unsaturated lower carbon chain group, or an alkylene group combined to form a ring. or a substituted alkylene group.) A method for producing an acetal compound represented by 3. The active ingredient is a general formula (wherein, X represents a halogen atom, a trifluoromethyl group or a lower alkyl group, and Y represents a halogen atom, a lower alkyl group or a lower alkyloxy group. Indicates an integer of 2. If the number is 2, X or Y may be the same or different. R1 and Rz each independently represent a saturated lower carbon chain group or an unsaturated lower carbon chain group. or an alkylene group or a substituted alkylene group that is combined to form a ring. .