JPH08310906A - Germicide - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain a new improved fungicide for agriculture and horticulture, especially useful for suppressing oomycetes by enhancing a fungicidal effect of cymoxanil by combining with a specific fungicidal compound, and a fungus is controlled by using the fungicide. SOLUTION: This fungicide combinedly uses (A) a compound of the formula (X is CH; Ra and Rb are each H, or Ra forms a covalent bonding together with Rb; Y is CH2 OCH3 ) with (B) cymoxanil, i.e., 1-(2-cyano-2- methoxyiminoacetylurea). A weight ratio of the (A/B) may be (1/0.3)-(1/3). Preferably, a compound in which X is CH, Ra and Rb are equally H and Y is CH2 OCH3 is used as the compound of the formula. Preferably, 100-400 g/ha of the A and 40-160 g/ha of the B are applied as the fungicide. A possibility of increasing of resistance of oomycetes against the suppressing effect by the compound of the formula is reduced by combinedly using the compound of the formula with cymoxanil.

Description

Detailed Description of the Invention

[0001]

FIELD OF THE INVENTION The present invention relates to an improved method for bactericides,
More specifically, it relates to an improved novel agricultural and horticultural germicide and a germicidal method using the same.

[0002]

The bactericide used in the present invention is particularly useful for controlling oomycetes. Although a wide variety of fungicides are known, including various oomycete control fungicides, there is a need for more effective fungicides.

[0003]

According to the present invention, (a) Formula I

Embedded image [Wherein, X is CH, Ra and Rb are both H, or both are combined to form a covalent bond, and Y represents CH ₂ OCH ₃ ], and (b) 1- (2-cyano It has been found that 2-methoxyiminoacetyl) -3-ethylurea (hereinafter referred to as a general name Cymoxanil) can be used in combination to suppress or control the diseases of agricultural and horticultural crops caused by pathogenic fungi. It was

Compounds of formula I useful as fungicides to control fungi include compounds wherein X, Ra, Rb, Y are the following groups: (i) CH, H, H, CH _2- , respectively. OCH ₃ (generic name: metalaxyl), (ii) CH, covalent bond (Ra + Rb), CH ₂ O, respectively
CH ₃ . Compound [I] is known or can be produced by a conventional method.

Cymoxanil is Plasmopar
It is a known systemic fungicide of bacterial cells having a bactericidal effect against a spp. (downy mildew) and Phytophthora spp.

Surprisingly, the use of cimoxanil in combination with a compound [I] according to the invention, for example with the compounds (i) to (ii) above, surprisingly substantially enhances the bactericidal effect of the compound [I] against the above fungi. It has also been found that the bactericidal effect of cimoxanil can also be substantially enhanced. When compound [I] is used in combination with cimoxanil, the risk of increased resistance of oomycetes to the inhibitory effect of compound [I] is significantly reduced. Also Phytophth
ora spp. and Plasmopara spp. of the invention, as demonstrated by a large reduction in the resistance coefficient (the ratio of bactericidal activity to resistant and susceptible strains at 90% concentration of active substance) of acylalanine-resistant field strains of the invention. The method shows significant activity against acylalanine resistance. An acylalanine-resistant field strain is an acylalanine-type fungicide (eg, Pesistance to acylalanine-type fungic
ides in Peronosporales (Phytopathology 71 (5)
558 (1981))]. Furthermore, the method of the present invention exhibits a broader range of efficacy than the inhibitory activity exhibited when the active ingredient is used alone against fungi.

Therefore, the present invention provides a bactericidal effective total amount of Compound [I] and Simoxanil, especially in places of agricultural and horticultural crops and eucalyptus trees in the cultivation of grape fruit trees, tomatoes, hops, cacao, tobacco, potatoes and lettuce. , In a mixture or by applying both active ingredients separately, in the field of agricultural and horticultural crops, in particular Phytophthor
a spp., Plasmopara spp., Peronospora spp., Pseu
doperonospora spp., Sclerophthora spp., Bremia s
It is possible to provide an improved method for controlling fungi belonging to the class Oomycetes such as pp. and Pythium spp.

The term agro-horticultural crop herein includes the meaning of development of the desired crop.

The compound [I] is 100 to 400 g / ha.
(Particularly 150-300 g / ha, for example 200 g / ha) at a rate of 40-160 g / ha of cimoxanil (particularly 60-12)
0 g / ha, eg 80 g / ha) or fosetyl-Al 75
It is used in combination with 0 to 2500 g / ha (particularly 1000 to 2000 g / ha, for example 1500 g / ha). In order to enhance the activity of the composition of the invention or to extend the range of its activity, other pesticides may be added to the active ingredients of said composition, such as other fungicides, bactericides, insecticides, bactericides. Mites, herbicides or plant growth regulators can be used. The additional use of contact bactericides in the process according to the invention is particularly advantageous.

Contact disinfectants that are specifically noted for use with the disinfectant of the present invention include copper disinfectants (eg, cuprous oxide, copper (II) oxychloride, cupric hydroxide, calcium copper sulfate (II). ), Calcium copper oxychloride (copper (II), Bordeaux mixture or Burgundy mixture), captan, diclofluanide, polypet, mancozeb, maneb, zineb, chlorothalonil, propineb, dithianon or a mixture thereof. The above-mentioned contact bactericide added to the bactericide of the present invention is generally 200 to 2000 g / g.
It can be used in the proportion of ha. Mancozeb is particularly suitable for use in the sterilization method of the present invention. Mancozeb has a special synergistic effect on the composition of compound [I] with cimoxanil.

The present invention can also provide a fungicide containing compound [I] and cimoxanil.

In the fungicide of the present invention, the compound [I]:
The weight ratio of cimoxanil is preferably 10: 1 to 1: 3,
More preferably 5: 1 to 1: 1 (particularly 4: 1 to 2: 1)
(For example, 2.5: 1)). The synergistic effect of the active ingredient is clear from the test data of various species in the table below. The synergistic effect in this test is especially indicated by a numerical value in the range of 1: 0.3 to 1: 3 compound [I]: cymoxanil weight ratio.

When the disinfectant of the present invention further contains a contact disinfectant, the weight ratio of compound [I]: contact disinfectant is preferably 1: 2 to 1:10, and mancozeb, holpet, captan or maneb. Is more preferably 1: 4 to 1: 9, particularly 1: 5 to 1: 8 (eg 1: 7). It is especially advantageous to incorporate mancozeb in the fungicide of the invention.

The bactericide of the present invention can be used as a usual drug type, for example, a pair of packages mixed with a diluent acceptable as a bactericide, a ready-to-use granule, or a flowable or wettable powder type. You can Such a fungicide composition can be formulated by a conventional method, for example, by mixing an active ingredient with a diluent (carrier) and other formulation ingredients (eg, a surfactant).

The term diluent as used herein refers to an agro-horticulturally acceptable liquid or solid substance which contains, in addition to the active ingredient, a fungicide composition of useful or preferred strength of activity (each readily It can be a drug form that can be used or modified). The diluent may be, for example, talc, kaolin, diatomaceous earth, xylene or water.

Particular drug types used as spray formulations, such as concentrated substances dispersible in water or dustable moisturizers, include humectants or dispersants (eg naphthalene sulfonates, alkylaryl sulfonates). , Lignin sulfonates, aliphatic alkyl sulphates, ethoxylated alkyl phenols or condensation products of ethoxylated aliphatic alcohols with formaldehyde).

Generally, such agents comprise from 0.01 to 90% (by weight) of the active ingredient, from 0 to 20% of a bactericide-acceptable surfactant and from 10 to 10 of a solid or liquid diluent.
99.99% and the active ingredient contains at least one compound [I] together with simoxanil and optionally other active substances (especially contact fungicides). Concentrated fungicide compositions generally have about 2-80% of active material added thereto.
(Weight), preferably 5 to 70%. The applied drug form may contain the active substance in an amount of, for example, 0.01 to 20% by weight, preferably 0.01 to 5% by weight.

Next, preferred embodiments of the present invention will be described with reference to examples (parts and% in the examples mean parts by weight and% by weight, respectively).

[0019]

【Example】

Test A: Phy having resistance to acylalanine type fungicides
Bactericidal effect against tophthora infestans strain Potato planted young tomatoes and potato plants (3-5 leaf development stage) are spray treated with the following aqueous liquid mixture for spraying: Mixture A-Compound [I] 0. 05-0.0002% and Simoxanil 0.05-0.0002% included, Mixture B-Compound [I] 0.05-0.0002% and mancozeb, folpet, captan, diclofluanid,
Contact disinfectant such as maneb or copper disinfectant 0.2-0.0
Contains 03%.

After 2 hours (or 4, 8, 16, 32 or 64 hours), the treated plants or their leaves are strongly washed with a provisional rainfall washing device at a rainfall rate of 10 to 50 mm / hour. Phytophthora infestans with enhanced resistance to compound [I] after 2 hours of washing treatment
Spore suspension of strain (10 ⁵ sporangia / ml)
Are inoculated into the drug-treated plants or leaves. The plant is transferred to a tent equipped with an atmospheric temperature of 16 ° C., an atmospheric relative humidity of 100%, and a sunshine time of 16 hours. After 4 to 5 days, the degree of disease control is evaluated by comparing the plant (leaf) treated with the drug with the plant (leaf) similarly inoculated without the drug treatment. In the case of the drug mixture A, complete inhibition of fungal disease is observed, but the degree of bactericidal activity of the mixture B is significantly less clear. Similar results show that Plasmopara viticola is resistant to acylalanine fungicides.
Obtained in grape fruit trees against the (Downy mildew of grapevine) strain.

Test B: Synergistic activity In this test, the fungicidal activity given by each of compound [I] and cimoxanil is compared with the fungicidal activity given when compound [I] is used in combination with cymoxanil. The possible existence of a synergistic effect of the two active ingredients is established by the Colby equation:

[Equation 1] [In the formula, A and B are bactericidal activities when each active ingredient is used alone, and p is a bactericidal activity theoretically obtained whether or not there is an interaction of the active ingredients in the mixture. ].

If p is lower than the experimentally determined bactericidal effect, a synergistic effect exists. Potato seedlings planted in pots are sprayed with an aqueous spray liquid containing either compound [I] and Simoxanil alone or in combination according to the invention.
Compound [I] and cimoxanil were 0.0 until the end of the treatment.
Used at a concentration of 125-0.00002%.

After 2 hours, the plants treated with the drug were treated with Phytophth.
The plant was inoculated with a spore suspension of ora infestans, and this plant was subjected to an atmospheric temperature of 16 ° C, an atmospheric relative humidity of 100%, and a sunshine duration of 16
Equip it in time and move it to the tent. After 4 to 5 days, the degree of disease inhibition is evaluated by comparing the plant treated with the drug with the plant similarly inoculated without the drug treatment. Plasmop
A similar test was carried out using a grape fruit tree exposed to ara viticola.

The pharmacological effects obtained are shown in the following table. In the table, Comp is the compound [I], Cym is cimoxanil, M is mancozeb, the underlined values are p (Colby) values, and the non-underlined values are the bactericidal effects determined by experiments.

[0025]

[Table 1]

[0026]

[Table 2]

[0027]

[Table 3]

[0028]

[Table 4]

[0029]

[Table 5]

Tables I to V (showing synergistic effects of active ingredients)
Based on the results of, the synergistic factor can then be calculated by the following Wadley equation:

[Equation 2]

In the formula, a, b and the like are weight ratios of the active ingredient used in the drug mixture, and EC90, EC90 (experimental value) and EC90 (theoretical value) are the values when the active ingredient is used alone. 90% inhibitory permissible concentration of the active ingredient (determined experimentally), 90% inhibitory permissive concentration of the mixture of active ingredients (determined experimentally) and 9 of the mixture of active ingredients
It is a 0% inhibition permissible concentration (determined by calculation). SF represents a synergistic coefficient (if there is a synergistic effect of the active ingredient, S
F ≧ 1).

Testing of tomatoes (Phytophthora infestans infection) with a compound [I] / simoxanil mixture under greenhouse conditions and grape vines (Plasmopara viticola) with a compound [I] / simoxanil / mancozeb mixture.
The synergistic effect (SF) was found by the infection test. The following table shows the results calculated according to Waddley.

[Table 6] Note) *: Weight ratio, see (2) Wadley.

Examples AF (preparation of wettable powder)

TABLE 7 Component A B C D E F (wt%) Compound ^{[I] (1) 8 10} 10 40 10 25 cymoxanil 3.2 5 10 24 5 10 Contact fungicides ⁽²⁾ 56 25 - - 25 - copper oxychloride (II) − 10 − 17.5 Calcium sulfate copper (II) − 5 − 18.5 Holpet − − 30 − Surfactant: Wetting agent ⁽³⁾ 1 1 1 1 1 1 Dispersant ⁽⁴⁾ 5 5 5 5 5 5 Diluent : Silica 5 5 5 5 5 5 Kaolin 21.8 34 39 25 13 54 Note) (1) For example, compound [I], (2) eg mancozeb, (3) eg sodium alkylnaphthalene sulfonate, (4) eg lignin sulfonic acid Natrium.

The above components were mixed, the mixture was crushed, and the mixture was mixed by a conventional method to obtain a dust. Generally, the active ingredient is used in industrial form. Examples of formulations containing technically active ingredients are listed below.

Example G Compound [I] (95% industrial) 10.5%; Simoxanil (95% industrial) 5.3%; Mancozeb (80% industrial) 31.3%; Copper oxychloride (II) ) (Copper 57%) 17.
5%; calcium sulfate copper (II) (copper 27%) 18.7
%; Surfactants and silica 11.0%; Kaolin 5.7
%.

Example H (flowability, 440 g / l) Compound [I] (95% industrial) 4.2% (w / w); Simoxanil (95% industrial) 1.7% (w / w) Mancozeb (80% for industrial use) 35.0% (w / w); Surfactant 4.
0% (w / w); 1,2-propylene glycol (antifreeze) 6.0% (w / w); adhesive 0.3% (w / w); stabilizer (eg citric acid) 5% (w / w); water 48.3%
(W / w); total 100% (w / w). The above components were mixed, wet-milled, and mixed to obtain a drug.

Example J (Granule, 67% (w / w) WG) Compound [I] (95% industrial) 8.4% (w / w); Simoxanil (95% industrial) 3.4% (W / w); Mancozeb (80% for industrial use) 70.0% (w / w); Dispersion / binder (eg sodium lignin sulfonate) 7.7% (w
/ W); stabilizer (eg citric acid) 0.5% (w / w).
The above components were mixed and ground, and granulated by flat plate granulation or fluidized bed granulation. The granules disperse well in water to form a sprayable suspension.

Claims (7)

[Claims] 1. In the location of the fungus, (a) Formula I: [Wherein, X represents CH, Ra and Rb are both H, or both are combined to form a covalent bond, and Y represents CH ₂ OCH ₃ ], and (b) 1- (2-cyano -2-methoxyiminoacetyl)
A method for controlling fungi, which comprises applying 3-ethylurea. 2. The method according to claim 1, wherein the compound (a) is applied in an amount of 100 to 400 g / ha and the compound (b) is applied in an amount of 40 to 160 g / ha. 3. A method according to claim _{2 wherein} X is CH, Ra and Rb are both H, and Y is CH ₂ OCH ₃ . 4. (a) Formula I: [Wherein, X represents CH, Ra and Rb are both H, or both are combined to form a covalent bond, and Y represents CH ₂ OCH ₃ ], and (b) 1- (2-cyano -2-methoxyiminoacetyl)
A synergistic fungicide for agricultural and horticultural use, which comprises 3-ethylurea. 5. The agent according to claim 4, wherein X is CH, R a and R _b are both H, and Y is CH ₂ OCH ₃ . 6. The weight ratio of compound (a) to compound (b) is 1.
The agent according to any one of claims 4 and 5, which is 0: 1 to 1: 3. 7. The agent according to claim 6, wherein the weight ratio of the compound (a) to the compound (b) is 1: 0.3 to 1: 3.