JPH08291002A - Fungicide for agricultural and horticultural use - Google Patents

Abstract

PURPOSE: To obtain a fungicide exhibiting excellent controlling effect on various plant blights, especially powdery mildew of various crops and black spot of pear. CONSTITUTION: This fungicide for agricultural and horticultural use contains an amine compound expressed by the formula H2 N-R-NH2 , H2 N-R<1> -X-R<2> -NH2 or H2 N-R<3> -NH-R<4> -NH-R<5> -NH2 (R is an 8-18C straight-chain alkyl; R<1> and R<2> are each independently a 3-12C straight-chain alkylene; R<3> , R<4> and R<5> are each independently a 6-10C straight-chain alkylene; X is NH, O or S) or its acid addition salt.

Description

Detailed Description of the Invention

[0001]

FIELD OF THE INVENTION The present invention relates to an agricultural and horticultural fungicide having an excellent controlling effect.

[0002]

2. Description of the Related Art Some plant diseases are susceptible to the emergence of resistant bacteria to control agents, which is an important problem in crop cultivation. For example, powdery mildew is a difficult-to-control disease that occurs widely in crops such as vegetables, fruit trees, wheat, tobacco and flowers, and as a controlling agent, 1,2-bis (3-methoxycarbonyl-2-thioureido) benzene, Methyl-1-
(Butylcarbamoyl) -2-benzimidazole carbamate, benzimidazole fungicides such as 2- (4-thiazolyl) benzimidazole, 1- (4-chlorophenoxy) -3,3-dimethyl-1- (1,2) , 4-triazol-1-yl) -2-butanone (hereinafter referred to as triadimefone), (E) -4-chloro-α, α, α-trifluoro-N- (1-imidazol-1-yl-2-
Propoxyethylidene) -O-toluidine, 2,4'-
N-heterocyclic ergosterol biosynthesis inhibitors such as dichloro-α- (pyrimidin-5-yl) benzhydryl alcohol and the like have been put to practical use and widely used. Pear black spot disease is a difficult control disease that is the most problematic in the cultivation of the main varieties of Japanese pear in the 20th century, and as a control agent,
3- (3,5-dichlorophenyl) -N-isopropyl-2,4-dioxoimidazolidine-1-carboxamide (hereinafter referred to as iprodione), 5-[[2-amino-
5-O- (aminocarbonyl) -2-deoxy-L-xylonoyl] -1,5-dideoxy-1- [3,4-dihydro-5- (hydroxymethyl) -2,4-dioxo-1 (2H) A polyoxin complex mainly containing -pyrimidinyl] -β-D-alofuranuronic acid has been commercialized and widely used. However, recently, resistant bacteria to these fungicides have appeared, and the deadlock of control is getting serious.

Sulfur and potassium hydrogen carbonate are drug-resistant powdery mildew fungi against aluminum = tris (ethylphosphonate), zinc dimethyldithiocarbamate, bis (dimethylthiocarbamoyl) disulfide, and organic copper are drug-resistant black spot fungus. On the other hand, although each is effective, it is necessary to spray a high-concentration drug, and its controlling effect is not sufficient. Therefore, there is a demand for a new drug having a sufficient controlling effect against not only general plant pathogens but also drug-resistant bacteria.

Regarding amine compounds, an example of being used as a chemical damage reducing agent for a specific herbicide is disclosed in JP-A-52-15.
4523, JP-A-53-18733, JP-A-53-53
No. 94035, but none of them describes the use of the amine compound of the present invention as an agricultural / horticultural fungicide. An example of being used as an agricultural / horticultural fungicide is disclosed in the former Soviet Union Patent 1769404, but there is no description about the use of the amine compound of the present invention as an agricultural / horticultural fungicide, and the compound of the present invention is In contrast to having a structure of primary or secondary amine, the compound of the Soviet patent is a tertiary amine, and there is a drawback that a quaternary ammonium salt is easily produced as a by-product in the production process.

[0005]

DISCLOSURE OF THE INVENTION The present invention provides a fungicide for agricultural and horticultural use that overcomes the above-mentioned drawbacks of the prior art and has an excellent control effect against drug-resistant bacteria.

[0006]

Means for Solving the Problems As a result of various studies to solve the above problems, the present inventors have found that polyamines and related compounds present in living organisms are effective against general plant pathogenic bacteria and existing drug-resistant bacteria. In particular, they have found that they have an excellent control effect against powdery mildew of various crops and diseases caused by Alternaria spp., Such as pear black spot disease, and completed the present invention. That is, the present invention provides the following general formula (1), (2) or (3)

[0007]

Embedded image H ₂ N—R—NH ₂ (1) H ₂ N—R ¹ —X—R ² —NH ₂ (2) H ₂ N—R ³ —NH—R ⁴ —NH—R ⁵ —NH ₂ (3) (In the formula, R represents a linear alkylene group having 8 to 18 carbon atoms, R ¹ and R ² each independently represent a linear alkylene group having 3 to 12 carbon atoms, and R ³ and R ⁴ And R ⁵ each independently represent a linear alkylene group having 6 to 10 carbon atoms, and X is N
H, O or S) is contained as an active ingredient in the amine compound or acid addition salt thereof.

R of the amine compound represented by the general formula (1)
Is a straight-chain alkylene group having 8 to 18 carbon atoms, and from the viewpoint of controlling effect, for example, a decamethylene group, a dodecamethylene group, a tetradecamethylene group or the like having 10 to 1 carbon atoms.
The alkylene group of 4 is preferred, and a dodecamethylene group is particularly preferred.

R of the amine compound represented by the general formula (2)
₁ and R ₂ are each independently a linear alkylene group having a carbon number of 3 to 12, and from the viewpoint of controlling effect, for example,
Preferred are alkylene groups having 6 to 10 carbon atoms such as hexamethylene group, octamethylene group, nonamethylene group and decamethylene group, and it is particularly preferred that both R ₁ and R ₂ are octamethylene groups. Further, X in the general formula (2) is NH, O or S, preferably NH.

Further, R ³ , R ⁴ and R ⁵ of the amine compound represented by the general formula (3) are each independently a straight-chain alkylene group having 6 to 10 carbon atoms, which is effective in controlling. From the above, for example, an alkylene group having 7 to 9 carbon atoms such as a heptamethylene group, an octamethylene group, and a nonamethylene group is preferable, and it is particularly preferable that R ³ , R ^4, and R ⁵ are all octamethylene groups.

The acid used to form the acid addition salt includes
For example, alkylbenzene sulfonic acid, preferably alkylbenzene sulfonic acid having 1 to 18 carbon atoms in the alkyl group,
More preferably, a sulfonic acid such as an alkylbenzenesulfonic acid having 10 to 13 carbon atoms having an alkyl group having 12 carbons as a main constituent (hereinafter referred to as albesyl acid), oleic acid, acetic acid, oxalic acid, lauric acid, formic acid, and propione. Examples thereof include carboxylic acid such as acid, organic acid such as organic sulfuric acid such as lauryl sulfuric acid, and inorganic acid such as hydrochloric acid, carbonic acid, sulfuric acid and phosphoric acid. The type of such an acid addition salt can be appropriately selected depending on the shape of the desired amine compound, the dosage form as a bactericide, and the like.

The amine compound of the present invention is a known compound and can be easily synthesized or obtained by those skilled in the art. The amine compound represented by the above general formula (1) is widely used as an industrial raw material and is easily available. The amine compounds represented by the general formulas (2) and (3) can be easily produced in one step by a reaction using the compound of the general formula (1) as a raw material and a catalyst. Since by-products other than ammonium gas are not generated along with the reaction, there is no need for post-treatment. Next, Table 1 shows typical examples of the amine compound represented by the above general formula (1) or an acid addition salt thereof.

[0013]

[Table 1]

[0014]

[Table 2]

Next, Table 2 shows typical examples of the amine compound represented by the general formula (2) or its acid addition salt.

[0016]

[Table 3]

[0017]

[Table 4]

[0018]

[Table 5] Next, Table 3 shows typical examples of the amine compound represented by the general formula (3) or an acid addition salt thereof.

[0019]

[Table 6]

[0020]

[Table 7]

The amine compound or the acid addition salt thereof according to the present invention can be prepared by using auxiliary agents such as solvents, carriers and surfactants which are generally used in the formulation of agricultural chemicals, for example, wettable powders, solutions, emulsions and flowables. It is formulated into an agent, powder, etc. and put into practical use.
Examples of the carrier and the solvent include clay, talc, calcium carbonate, bentonite, kaolin, water, methyl alcohol, propylene glycol, acetone, methyl ethyl ketone, cyclohexane, dioxane, xylene, methylnaphthalene, tetrahydronaphthalene, dimethylchlorobenzene, dimethylformamide, ethyl acetate. , Acetonitrile, dimethyl sulfoxide and the like. Examples of the auxiliary agent include naphthalene sulfonic acid sodium salt formalin condensate, polyoxyethylene alkyl ether, polyoxyethylene alkyl phenyl ether,
Examples thereof include polyoxyethylene dinonylphenyl ether sulfate ammonium salt, lauryl sulfate sodium salt, ligninsulfonic acid sodium salt, polyvinyl alcohol, and white carbon.

The agricultural and horticultural fungicide according to the present invention is effective not only against general plant pathogenic bacteria but also against existing drug-resistant bacteria. For example, rice, wheat, buckwheat, potato, adzuki bean, green beans and peas. , Cowpea, soybean, lima beans,
Peanut, strawberry, turnip, pumpkin, mustard, cabbage, cucumber, burdock, shirouri, watermelon, Japanese radish, capsicum, pepper, tomato, eggplant, carrot,
Chinese cabbage, lotus, bell pepper, butterbur, squirrel, melon, swordfish, akebi, apricot, ume, sweet cherry, oyster, quince, citrus, chestnut, walnut, currant, plum, pear, pear, papaya, grape, peach, apple, Atsutsurafuji , Flaxseed, American terrestrialis, sumac, Coptis chinensis, Jerusalem artichoke, mulberry, buckthorn, kozo, sesame, koyanagi, cigarette, tea, choma, tunaso, sugar beet, rapeseed, rapeseed, hazelnut, hop, flowers (cosmos, carnation, chrysanthemum, Sweet pea, rose, sunflower, begonia, etc.), grass, turfgrass,
It is applicable to various crops such as ornamental trees, and is particularly effective against powdery mildew such as vegetables such as cucumber and wheat, and diseases caused by Alternaria spp., Such as pear black spot.

When sprayed during the growing season of crops, a wettable powder, a liquid agent, an emulsion, a flowable agent, etc. are diluted with water and sprayed. Further, it can be sprayed by mixing with other insecticides, bactericides and the like. The content (% by weight) of the active ingredient in the preparation is usually 10-40% for wettable powders, 10-40% for liquid preparations, 10-30% for emulsions, 10-40% for flowable preparations,
It is 1 to 30% in powder. The amount of the active ingredient in the water-diluted solution at the time of spraying the wettable powder, emulsion and flowable agent varies depending on the target crop, etc., but is usually 20 to 1000 ppm, preferably 50 to 500 ppm, particularly preferably 80 to
It is in the range of 400 ppm. The amount of dust applied varies depending on the target crop, etc., but is usually 0.3 to 4 kg per 10 a in the crop growing season, and is usually 20 in the case of soil treatment.
~ 40 kg. However, the above-mentioned contents, component amounts, and application amounts are not limited to this range.

[0024]

EXAMPLES The present invention will be described below with reference to examples, but the amine compounds, carriers, surfactants and the like used are not limited to those listed in these examples. In addition, "part" below means a weight part.

[Example 1] Wettable powder Compound of Compound No. 10 20 parts Clay 62 parts Naphthalenesulfonic acid sodium salt formalin condensate 5 parts Lauryl sulfate sodium salt 3 parts White carbon 10 parts The above components are mixed and ground to hydrate I got an agent.

[Example 2] Wettable powder Compound of Compound No. 11 20 parts Clay 62 parts Naphthalenesulfonic acid sodium salt formalin condensate 5 parts Lauryl sulfate sodium salt 3 parts White carbon 10 parts The above components are mixed and ground to hydrate I got an agent.

[Example 3] Wettable powder Compound of Compound No. 57 20 parts Clay 62 parts Naphthalene sulfonic acid sodium salt formalin condensate 5 parts Lauryl sulfate sodium salt 3 parts White carbon 10 parts The above are mixed and pulverized to hydrate I got an agent.

[Example 4] Wettable powder Compound of compound No. 58 20 parts Naphthalene sulfonic acid sodium salt formalin condensate 5 parts Clay 62 parts Lauryl sulfate sodium salt 3 parts White carbon 10 parts The above components are mixed, pulverized and hydrated I got an agent.

[Example 5] Wettable powder Compound of Compound No. 97 20 parts Naphthalenesulfonic acid sodium salt formalin condensate 5 parts Clay 62 parts Lauryl sulfate sodium salt 3 parts White carbon 10 parts The above components are mixed and ground to hydrate I got an agent.

Example 6 Liquid formulation Compound of Compound No. 60 25 parts Polyoxyalkylene alkylaryl ether 5 parts Water 70 parts The above components were mixed in a tank to obtain a liquid formulation.

Example 7 Emulsion Compound No. 60 10 parts Alkylallyl sulfonate 5 parts Polyoxyalkylene alkylaryl ether 5 parts Xylene 80 parts The above components were mixed in a tank to obtain an emulsion.

[Example 8] Flowable agent Compound of Compound No. 60 10 parts Polyvinyl alcohol 5 parts Polyalkylene alkylaryl ether 5 parts Ethylene glycol 5 parts Water 74.9 parts The above components were uniformly stirred and dispersed, and then Xandum 0.1. Parts were added and mixed to obtain a floor-blending agent.

Example 9 Dust Compound 3 of Compound No. 58 3 parts Talc 94 parts White carbon 3 parts The above ingredients were mixed and ground to obtain a powder.

Next, the bactericidal effect of the amine compound or its acid addition salt according to the present invention will be shown by test examples. The following drugs were tested as control drugs. [Control drug 1] A commercially available triadimefon wettable powder (manufactured by Japan Bayer Agrochem Co., Ltd.) was tested. [Control drug 2] A commercially available potassium hydrogencarbonate aqueous solvent (manufactured by Toagosei Chemical Industry Co., Ltd.) was tested. [Control drug 3] A commercially available iprodione wettable powder (manufactured by Rhone Poulin Agro Co., Ltd.) was tested.

[Test Example 1] Cucumber powdery mildew control effect test (field test) Cucumber under conventional cultivation in a greenhouse (variety: Antarctica No. 2)
12 strains were tested per drug. A 10-leaf stage cucumber at the start of the test was sprayed with a water-diluted solution of a wettable powder prepared according to the same mixing ratio as in Example 1 three times at an interval of one week using a power sprayer so that the leaf surface was sufficiently wet. 3 days after the final application,
The pathogenic state of powdery mildew naturally occurring in the top 10 leaves was investigated according to the following criteria, and the disease degree was calculated by the formula 1, and the control value was calculated by the formula 2. The results are shown in Table 4. Index 0: Disease-free 1: Lesion area is less than 10% of leaves 2: Lesion area is 10% or more and less than 25% of leaves 3: Lesion area is 25% or more and less than 50% of leaves 4: Lesion area is 50% or more of leaves

[0036]

[Equation 1]
Formula 1

[0037]

Equation 2

[0038]

[Table 8]

The compounds of Compound Nos. 1, 10, 20 and 30 showed a high controlling effect in the field where the controlling effect of triadimefon was lowered. Moreover, the control effect was superior to the potassium hydrogencarbonate aqueous solvent.

[Test Example 2] Cucumber powdery mildew control effect test (field test) Cucumber under conventional cultivation in a greenhouse (variety: Antarctica No. 2)
Was tested for 4 strains per drug. Cucumber in the 15th leaf stage,
A water-diluted liquid of a wettable powder prepared according to the same mixing ratio as in Example 1 was sprayed using a power sprayer until the leaf surface was sufficiently wet. Seven days after the spraying, the pathogenic state of powdery mildew naturally occurring in the top 10 leaves was investigated according to the criteria of Test Example 1, and the degree of disease was calculated by the above-mentioned formula 1 and the control value was calculated by the above-mentioned formula 2.
The results are shown in Table 5.

[0041]

[Table 9]

Compound Nos. 57, 58, 60, 64, 6
The compounds of 5, 66 and 67 showed a high control effect in the field where the control effect of triadimefon was reduced. In addition, the control effect was far superior to that of potassium hydrogencarbonate aqueous solvent.

[Test Example 3] Cucumber powdery mildew control effect test (field test) Twelve strains of cucumber (cultivar: Angkor 8) under conventional cultivation in a greenhouse were tested per drug. A cucumber at the 15th leaf stage was sprayed with a water-diluted solution of a wettable powder prepared according to the same mixing ratio as in Example 5 using a power sprayer until the leaf surface was sufficiently wet. Seven days after the spraying, the pathogenic state of powdery mildew naturally occurring in the top 10 leaves was investigated according to the criteria of Test Example 1, and the degree of disease was calculated by the above-mentioned formula 1 and the control value was calculated by the above-mentioned formula 2. Table 6 shows the results.

[0044]

[Table 10] The compounds of Compound Nos. 88, 96, 97 and 113 showed a high control effect in the field where the control effect of triadimefon was reduced. In addition, the control effect was far superior to that of potassium hydrogencarbonate aqueous solvent.

[Test Example 4] Cucumber powdery mildew control effect test (pot test) One cucumber (cultivar: Shintokiwa) with fully developed cotyledons was used.
Six strains were tested per drug. A water-diluted solution of a wettable powder prepared according to the same compounding ratio as in Example 1 was sprayed using a hand sprayer so that the leaf surface was sufficiently wet. 14 days after the spraying, the pathogenic state of powdery mildew naturally occurring on the cotyledons was investigated based on the criteria of Test Example 1, and the degree of disease was calculated by the above mathematical formula 1 and the control value was calculated by the mathematical formula 2. The results are shown in Table 7.

[0046]

[Table 11]

Compound Nos. 32, 37, 46, 57, 5
The compounds of Nos. 8, 72, 77 and 85 showed a high controlling effect under the condition that the controlling effect of triadimefon was low. In addition, the control effect was far superior to that of potassium hydrogencarbonate aqueous solvent.

[Test Example 5] Pear black spot disease control effect test Japanese pear (variety: twentieth century) pot-cultivated was used for one tree per drug. A water-diluting solution of a wettable powder prepared according to the same compounding ratio as in Example 1 was sprayed on a pear tree in which young leaves were developed, using a manual sprayer, to such an extent that the leaf surface was sufficiently wet.
After air-drying, 5 young leaves were cut off per drug, and a conidial suspension of pear black spot fungus (spore concentration: 5
(× 10 ⁵ cells / ml) were evenly sprayed and allowed to stand in a moist chamber. Two
After 0 hours, the number of lesions occurring on the young leaves was investigated, and the control value was calculated according to Formula 3. Table 8 shows the results.

[0049]

Equation 3

[0050]

[Table 12]

Compound Nos. 10, 18, 41, 57 and 6
The compound of 6 showed a high control effect which was far superior to that of the iprodione wettable powder.

[0052]

INDUSTRIAL APPLICABILITY Agro-horticultural fungicides containing an amine compound represented by the general formula (1), (2) or (3) or an acid addition salt thereof are various plant diseases, especially powdery mildew of various crops. ,
It has an excellent control effect against pear black spot disease.

Claims (6)

[Claims] 1. The following general formula (1), (2) or (3): embedded image H ₂ N—R—NH ₂ (1) H ₂ N—R ¹ —X—R ² —NH ₂ (2 ^{_{) H 2 N-R 3 -NH}} -R 4 -NH-R 5 -NH 2 (3) ( wherein, R represents a linear alkylene group having 8-18 carbon atoms, R ¹ and R ² are each independently Represents a linear alkylene group having 3 to 12 carbon atoms, R ³ , R ⁴ and R ⁵ each independently represent a linear alkylene group having 6 to 10 carbon atoms, and X represents N.
A fungicide for agricultural and horticultural use, which comprises an amine compound represented by H, O or S) or an acid addition salt thereof. 2. R of the compound represented by the general formula (1) is
The agricultural / horticultural germicide according to claim 1, which is a linear alkylene group having 10 to 14 carbon atoms. 3. The fungicide for agricultural and horticultural use according to claim ^1, wherein R ¹ and R ² represented by the general formula (2) are each independently a linear alkylene group having 6 to 10 carbon atoms. 4. R ³ , R ⁴ and R represented by the general formula (3)
The agricultural and horticultural fungicide according to claim 1, wherein ⁵ are each independently a linear alkylene group having 7 to 9 carbon atoms. 5. A compound represented by the general formula (2), wherein X is
The agricultural / horticultural fungicide according to claim 1 or 3, which is NH. 6. A powdery mildew control agent comprising the amine compound or the acid addition salt thereof according to claim 1 as an active ingredient.