JPS63141905A - Agricultural and horticultural fungicide - Google Patents

Abstract

PURPOSE:To obtain an agricultural and horticultural fungicide exhibiting synergistic effect against alternaria blotch of apple, brown rot of peach, gray mol of various crops, etc., by combining a specific triazole derivative with either one of captan, captafol and folpet. CONSTITUTION:The objective agricultural and horticultural fungicide contains a mixture of (A) at least one kind of the triazole derivative of formula I (X1 and X2 are H, halogen or lower haloalkyl; Y1 and Y2 are H or halogen) (e.g. a compound wherein X1 and X2 are 2,4-Cl and Y1 and Y2 are 4-Cl) with (B) either one of captan of formula II (i.e. N-trichlo romethylthiotetrahydrophthalimide), captafol of formula III (i.e. N- tetrachloroethylthiotetrahydrophthalimide) or folpet of formula IV (i.e. N- trichloromethylthiophthalimide) as active components.

Description

DETAILED DESCRIPTION OF THE INVENTION A) Object of the Invention ■u2 "Old" The present invention relates to an agricultural and horticultural fungicide containing a mixture of a triazole derivative and a phthalimide derivative as an active ingredient.

More specifically, the present invention relates to the general formula [wherein X1 and X2 are the same or different and hydrogen atoms,
represents a halogen atom or a lower haloalkyl group, and Y and Y2 are the same or different and represent a hydrogen atom or a halogen atom. cabtan)
, N-tetrachloroethylthiotetrahydrophthalimide (Captafor) or N-trichloromethylthiophthalimide (Forbet) as an active ingredient.

(Left below) Forbent: The fungicide of the present invention is effective in controlling plant pathogens that cause great damage to various crops such as fruit trees, vegetables, and grains. The invention can therefore be used as a fungicide in the agricultural and horticultural fields.

Cabtan, captafol, and forbet, which are the active ingredients of the fungicide of the present invention, are known as agricultural fungicides, and can be used as a spray agent to control various diseases of vegetables, fruit trees, and grains, or applied to soil. It is widely used as a disinfectant and seed disinfectant. These drugs have a wide spectrum of pesticidal activity and are excellent drugs with no chemical toxicity. These things are “
Pesticide Handbook 1985 Edition” (Japan Plant Protection Association, published January 30, 1985), No. 183-1
It is described on page 84 (Kabtan), pages 186 to 188 (Kaptahol), and page 180 (Forbent) of the "1981 Edition" (published July 20, 1981).

In addition, mixtures containing one of these can be used as agricultural and horticultural fungicides, such as cabtane and thiabendazole, cabtane and benomyl, cabtane and fosetyl,
Regarding the combinations of cabtane and polyoxin B, cabtane and mepronil, cabtane and binabacryl, captafor and polyoxin B, etc., see pages 185-186 and 188 of the R, B Drug Handbook 1985 Edition.
It is written on the page etc. Incidentally, the names of the above-mentioned drugs such as cabtan are common names listed in the "Pesticide Handbook 1985 Edition".

On the other hand, the compound of formula (I) was discovered by the present inventors and is a known compound effective in controlling powdery mildew and rust on vegetables, scab on fruit trees, brown spot on beets, etc. Yes (Japanese Unexamined Patent Publication No. 58-65281). In addition, as a mixture containing the compound of formula (1), JP-A-59-
7105 (formula (I) compound + procymidone), JP-A-59-7103 (formula (1) compound kasugamycin), JP-A-59-13703 (formula (1) compound + polyoxin group antibiotics) ), JP-A-59
- Publication No. 16803 (formula (I) compound + iprodione, vinclozolin), JP-A-59-1 (publication No. 3803 (formula (I> compound dried benomyl, 1,000 ophanate methyl,
Thiabendazole, MBC2-(methoxycarbonylamino)-benzimidazole) and the like are known. The names in parentheses are the common names listed in the "Pesticide Handbook 1985 Edition". However, it is not known that a mixture of a phthalimide compound such as cabtan, captafol, or forbet and a compound of formula (I) can be used as a fungicide for agricultural and horticultural purposes.

Cabtan, captafol, and forbet, which are phthalimide compounds that are one of the active ingredients of the present invention, have a wide spectrum of pesticidal activity, are non-selectively effective against various diseases, and have been effective for many years. Despite its use, it has excellent properties that prevent the development of drug-resistant bacteria. However, high-dose spraying is required for disease control, and preventive spraying is required before the disease appears; spraying after the disease has invaded the plant is ineffective; However, the effect is somewhat insufficient under frequent conditions, and there are problems in terms of economics and labor, such as the need to increase the number of sprayings.

The other active ingredient, the compound of formula (I), is effective against mildew on wheat, soybeans, alliums, grapes, pears, apples, flowers, etc., and powdery mildew on cucumbers, melons, strawberries, wheat, roses, etc. It shows a high control effect at a low dose, and also controls rice and sesame leaf blight, cucumber and melon vine blight, cucumber, anthracnose, and gray mold of cucumber, lettuce, strawberry, eggplant, etc. Although effective, high doses are required to achieve sufficient control.

The present inventors have discovered that these drawbacks can be compensated for and a stable synergistic control effect can be exhibited at low doses.

The present inventors have conducted intensive research to develop a PC horticultural fungicide that compensates for the drawbacks of the above-mentioned conventional fungicides and takes advantage of the excellent properties of its active ingredients. Completed the invention.

According to the present invention, a fungicide for agriculture and horticulture is characterized in that it contains a mixture of at least one triazole derivative having the formula (I) and any one of cabtan, captabol, or forbet as an active ingredient. is provided.

In the formula (I), Xl, X2. Yl and Y2 can each be substituted at any position of the benzene ring to which they are bonded. Xl and X2 are independently hydrogen atoms,
Halogen atoms (e.g. fluorine, chlorine, bromine or iodine) or lower haloalkyl groups [e.g. tri(or di or mono-)fluorolomethyl, tri(or di or mono)chloromethyl, tri(or di or mono)bromomethyl , 2,2.2-trifluoro(or chloro or bromo)ethyl, 2,2-difluoro(or chloro or bromo)ethyl, etc.). Y and Y2 independently represent a hydrogen atom or a halogen atom (eg fluorine, chlorine, bromine or iodine).

Preferred specific examples of triazole derivatives having the formula (I>) used in the present invention are shown in Table 1, but it goes without saying that the scope of the present invention is not limited thereto.

In the agricultural and horticultural fungicide of the present invention, the combination of Im selected from cabtan, cabtafor, or forbet and the compound of formula (I) is effective against powdery mildew on vegetables, apples, and pears. Diseases, red leaf spot, leaf spot disease, apple spot leaf spot, peach leaf spot, leaf spot, peach leaf spot, gray leaf spot, grape black leaf spot, beet, groundnut brown leaf spot, tomato leaf mold, strawberry gray leaf spot It acts as an active ingredient for controlling mildew and wheat starch disease. When these active ingredients are used in combination, they exhibit a synergistic effect on apple leaf spot disease, peach leaf spot disease, gray mold disease on various crops, etc., compared to when they are used alone.

The reason why it exhibits such excellent effects is not necessarily clear, but the compound of formula (I) of the present invention inhibits the synthesis of ergosterol, an essential component contained in the cell membrane of pathogenic hosts, causing a loss of M function. On the other hand, cabtan, captafol, and forbet inhibit the growth of pathogenic bacteria by inhibiting the growth of pathogenic bacteria.
It is believed that it exerts its bactericidal action by reacting with the chemical group. This synergistic activity resulting from the mixture of two drugs with mutually different action characteristics is due to the reduction in the membrane function of pathogenic bacteria caused by the compound of formula (I), which facilitates the uptake of cabtan, kabtafor, and forbet into the bacterial body. It is presumed that this is because it becomes more powerful.

! Ui! J! I sentry
``The agricultural and horticultural fungicide of the present invention can be formulated into a wettable powder, emulsion, powder, granule, flowable, etc. by a conventional method together with the active ingredient, a carrier, and various additives. The carriers used include solid carriers such as clay, talc, bentonite, kaolin, diatomaceous earth, silica, and sucrose, or benzene, xylene, toluene, crocin, alcohols (methanol, ethanol, isopropanol, n- butanol, etc.), ketones (acetone,
Liquid carriers such as methyl ethyl ketone, cyclohexanone, etc.) are used. Appropriate surfactants and other auxiliary agents, such as stabilizers and spreading agents, are added to these.
It can be used by blending it into a formulation.

The blending ratio of the active ingredients in the present invention is 181 by weight of any of cabtan, captafol, or forbet.
It is appropriate to mix the compound of formula (I) in a proportion of 0.01 to 0.2 parts per part. However, the blending ratio can be changed as appropriate depending on the conditions at the time of application.

It is also possible to mix and use other fungicides, insecticides, herbicides, plant growth regulators, etc.

Next, examples of the present invention will be shown. In the examples, all parts are g1# parts.

60 parts of cabtan, 13 parts of compound yang, 10 parts of white carbon, 3 parts of lauryl sulfate, 2 parts of calcium lignosulfonate, and 22 parts of clay were mixed and thoroughly ground to obtain a wettable powder.

40 parts of Kabutafor, 23 parts of Compound Lu, 10 parts of white carbon, 3 parts of lauryl sulfate, 2 parts of naphthalene sulfonic acid soda formalin condensate, and 42 parts of clay are mixed and thoroughly ground to obtain a wettable powder.

50 parts of Forbet, 55 parts of Compound Lu, 10 parts of white carbon, 3 parts of lauryl sulfate, 2 parts of calcium lignosulfonate, and 30 parts of clay were mixed and thoroughly ground to obtain a wettable powder.

42 parts of Flopur water, 1 part of polyoxyethylene nonylphenyl ether, and 4 parts of lignin-sulfonate sodium salt were stirred, and then 40 parts of finely ground cabtan and 1 kl of the compound were mixed.
A flowable is obtained by adding 3 parts and stirring, and further adding 10 parts of a 2% xanthan gum aqueous solution and stirring.

The method of using the agricultural and horticultural fungicide of the present invention is generally as follows. That is, in the case of wettable powders, emulsions, and sol preparations (flowable preparations), dilute them 500 to 2000 times with water.
Generally, it is prepared to a concentration of 10 to 1500 ppn. Then, apply this diluted solution at 50 to 400 N per 10 ares.
, usually in the range of 100 to 3001, is sprayed on the leaves and foliage of the plant where the disease occurs.

In addition, emulsions and sol formulations (flowable formulations) can be used as concentrated liquids without being diluted with water, or by diluting them up to 10 times with water and used as micro-spraying agents (LV spraying agents, ULV spraying agents) for aerial spraying. ), spray in an amount of about 50 to 300 ml per 10 are using a helicopter or the like.

In addition, for powders and granules, 2 to 5 kg per 10 Ir (approximately 50 to 500 Ir as an active ingredient) is added to the plant body.
±39 Apply to surface or water surface.

C) Effects of the invention When the agricultural and horticultural fungicide of the present invention is used, various plant diseases such as apple scab, red spot, powdery mildew, leaf spot, ring spot, black spot, and sooty spot can be prevented. , sooty spot, monilia disease, brown spot, pear spot, red spot, powdery mildew, black spot, peach leaf curl, scab, phomopsis rot, gray spot, grape late rot, brown spot, gray mold,
Black powdery mildew, powdery mildew, rust, gray blight of cherry, black blight of plum, Nitten leaf blight of persimmon, powdery mildew, powdery mildew of cucumber, melon, watermelon, capocha, anthracnose, downy mildew. Mildew, scab, powdery mildew of eggplant, powdery mildew of tomato, late blight, leaf mold, powdery mildew of strawberry, gray mold,
Mildew on green onions, anthracnose on tea, rope blast, rice blast, powdery mildew on wheat, rust, shin smut, sleep spot, beets, brown spot on groundnuts, scab on roses, powdery mildew , black spot, chrysanthemum white rust, black rust, grass rust, brown patch,
Shows high control effect on Pythium patch etc.

In this case, looking at the relationship between the blending ratio of active ingredients and the control effect, for 1 part (by weight, the same applies hereinafter) of the compound of formula (I), 10 to 25 parts for cabtan and folpet;
Captafor exhibits the highest synergistic control effect when 5 to 20 parts are blended.

In order to exhibit the excellent pesticidal effect as described above, the agricultural and horticultural fungicide of the present invention can be sprayed directly onto the plant foliage using an appropriate spraying device before or after the outbreak of the disease. can be effectively controlled, and is useful for crops such as apples, pears, peaches, grapes, cherry blossoms, plums, persimmons, cucumbers, melons, watermelons, lotus, tomatoes, strawberries, green onions, tea, barley, wheat, It does not cause any chemical damage to grass, peanuts, roses, chrysanthemums, grass, etc.

In addition, the agricultural and horticultural fungicide of the present invention has a completely different chemical structure from benzimidazole drugs such as benomyl and thiophanate methyl, or dicarboximide drugs such as vincloprine, iprodione, and protusidone, which are currently problematic. Since it is a combination of drugs, it acts equally or even more effectively against drug-resistant bacteria caused by benzimidazole drugs and dicarboximide drugs than against susceptible bacteria.

The synergistic activity of the phthalimide drugs of cabtan, captafol, and forbet and Compound Product 1, Compound Product 2, or Compound Product 5 was determined using the following paper cross method <[Pesticide Experiment Method 2 Sterilization] Drug Edition”
Published by Soft Science Company, March 31, 1982, No. 52~
53W).

Peach blight bacterium (Monilinia) on potato decoction agar medium
Fructii Cola Hon1liniarructic
Pour the spore suspension of o+a), mix well (spore concentration in the medium: 104 cells/ml), and dispense this into 91 veterinary dishes to form a solidified plate. A strip of filter paper (7 mm width,
8 cIm in length), air-dried under sterile conditions, placed perpendicularly on the agar plate, and incubated at 24°C for 2 days. Observed. If the growth inhibition zone is abnormally swollen, it is determined that there is a synergistic effect.Table 2 shows the results of determining the presence or absence of synergism between the two drugs.

(Left space below) Table 2 Synergistic effects of cabtan, cabtafor, or forbet and compounds 1, 2, and 5 on peach gray blight.As is clear from Table 2 above, the triazole derivatives of the present invention There is a synergistic effect between (I) and cabtan, captafol, and forbet, whereas there is no synergistic effect between thiophanate methyl and cabtan, etc.

Test Example 2 Test method (1) Test variety: Fuji 11th grade (2) District II: 1 district 1vI43 series (3) Chemical spraying, method: Water prepared according to Example 1 Using Japanese medicine, May 28th,
A power sprayer was used to spray 30j1 per tree a total of four times on June 10th, June 21st, and July 2nd.

(4) Disease outbreak status: Initially, the number of outbreaks was small, but from mid-June onwards, the number of outbreaks increased and became more frequent.

(5) Disease onset investigation: 14 days after the final spraying, randomly select 15 new shoots in each area and investigate all leaves for the presence or absence of disease (the average number of leaves surveyed is approximately 400), calculate the diseased leaf rate (%), and calculate the disease incidence rate (%). The control value was calculated. In addition, drug damage was investigated using the following indicators.

0: No disease onset 3: Frequent disease 1: Few 4: Very many 2: Medium The results are shown in Table 3.

(Left below) Table 3 Efficacy for controlling apple leaf spot leaf disease Table 3
(Continued) Note 1) The numbers in parentheses indicate the rate of diseased leaves in the untreated plot.

Note 2) This is a commercially available apple leaf spot control agent (trade name: Sunup).

(Left below) Examination J1 example - Once...
・Test method (1) Test variety: Chiaki 5th grade correction stand (2) Ward system
:1 ward 1 tree 33! ! System (3) Chemical spraying/method: Using a hydrating powder prepared according to Example 1, spraying was carried out on May 20th (just before flowering), May 30th (wheat directly from falling flowers), June 14th, June 6th. A total of 101 doses were applied per tree using a power sprayer a total of 4 times on the 30th day of each month.

(4) Disease outbreak status: Apple scab disease occurs frequently, and apple scab disease occurs moderately.

(5) Investigation of the onset of the disease On July 14th (14 days after the final application), all fully expanded leaves of 30 new shoots per 1 fM were investigated for the presence or absence of disease onset, and the incidence rate (%) of the leaves was determined. In addition, for Akaboshi disease, 15 days after the second spraying (June 14th),
The presence or absence of disease onset was investigated, the rate of diseased leaves (%) was determined, and the control value (%) was calculated from this comparison with the non-sprayed area. Also,
Investigate drug damage using the same indicators as Test Example 2. The results are shown in Table 4.

(Leaving space below) Table 4 Control effect on apple scab and scab blight Table 4 (Continued) Note 1) The numbers in parentheses indicate the rate of disease in the untreated plot (%).

Note 2) Product name Sunup (Cabtane % + Binabacryl 15%), Binapacryl is the chemical name 2,4-dinitro-6-secondary butyl phenyl dimethyl acrylate Note 3) Chemical name: Zinc ion coordination Manganese ethylene bisthio Commercially available carbamate wipe t[=4 Test method (1) Test variety Nihakuho 7th grade (2) Ward system: 1 ward 1 tree 33! ! Control (3) Chemical spraying/method: Using a hydrating powder manufactured by YU according to Example 1, a power injection S machine was used once just before sprouting (March 21st) to spray 71 ml per tree. Spread.

(4) Disease outbreak status: During the budding period from early April, there was a lot of rain and many occurrences occurred.

(5) Disease onset survey: Approximately 400 leaves per tree were investigated on May 25th for the presence or absence of disease onset, the diseased leaf rate (%) was determined, and the control value was calculated from this in comparison with the untreated plot. In addition, drug damage was expressed using the same index as in Test 2. 5th result
Shown in the table.

Table 5 Control effect on peach rice leaf disease Table 5 (continued) Note 2) Chemical name is 8-hydroxyquinolinic acid.

(Leaving space below) Test method (1) Test variety: Kyoho 5th grade (2) Ward system: 1 ward IFj 43 series (3) Chemical spray method: Wettable powder prepared according to Example 1 Twice on May 10th (emergence period) and May 25th, using a power blower,
201 was sprayed per tree.

(4) Disease outbreak status: There were many outbreaks.

(5) Disease onset investigation: On June 8th, 200 fruit clusters of each phase were investigated according to the degree of disease onset, and the degree of disease onset was determined by comparison with the non-sprayed area to determine the control value (%). ) was calculated. In addition, drug damage was investigated using the same indicators as in Test 2.

N: Number of fruit bunches investigated a: Number of fruit bunches with diseased grains of 11 or more in 1 fruit cluster b = Number of fruit clusters with diseased grains of 6 to 10 in 1 fruit cluster C: Nol of 1 fruit cluster Nol of 5 or less The results are shown in Table 6.

(Left below) Table 6 Control effect on grape ring rot Table 6 (Continued) Patent applicant Hokuyo Chemical Industry Co., Ltd. (2 idiots)

Claims (1)

[Claims] 1) General formula ▲ Numerical formula, chemical formula, table, etc. ▼ (I) [In the formula, X_1 and X_2 are the same or different and represent a hydrogen atom, a halogen atom, or a lower haloalkyl group, and Y
_1 and Y_2 are the same or different and represent a hydrogen atom or a halogen atom. ] At least one triazole derivative having N-
Trichloromethylthiotetrahydrophthalimide, N-
Either one of tetrachloroethylthiotetrahydrophthalimide or N-trichloromethylthiophthalimide
An agricultural and horticultural fungicide characterized by containing a mixture with seeds as an active ingredient.