JPS5925303A - Plant blight controlling agent containing oxathiazine derivative as active component - Google Patents

Abstract

PURPOSE:To provide the titled controlling agent effective to the plant blights such as rice blast, bacterial leaf blight of rice, bacterial spot of cucumber, etc., and free from phytotoxicity, by using an oxathiazine derivative as an active component. CONSTITUTION:The objective agent contains one or more oxathiazine derivatives of formula (R<1> is H, 1-10C straight or branched alkyl, aliphatic acyl residue, or phenyl; R<2> is H 1-10C straight or branched alkyl, or phenyl; R<1> and R<2> may together form substituted or unsubstituted cycloaliphatic or aromatic ring group) as active component. It can be applied as it is, or by diluting with water, solid powder or other proper carrier, and if necessary mixing with an adjuvant such as extender, etc. Rate of application; e.g. 2-10kg of granules or powder per 10 are for the control of blight of rice in paddy rice field.

Description

[Detailed description of the invention] [■] Background of the invention 1. Technical field The present invention relates to a plant disease control agent.

2. Prior Art The oxateazine derivative represented by the formula (11) and its production method are based on AngewandteC)1en+ie
Volume 2, No. 11, pp. 869-876 (1973), West German Patent Publication No. 2001017, West German Patent Publication No. 2434562 and West German Patent Publication No. 2434562, and Japanese Unexamined Patent Publication No. 716-2
It is described in Publication No. 8, etc.

(However, H represents a hydrogen atom, a straight nail with 01 to 100 carbon atoms, a branched alkyl group, an aliphatic acyl residue, or a phenyl group, and R2 represents a hydrogen atom, a straight chain or branched alkyl group having 1 to 10 carbon atoms, or phenyl Represents a group 1-0R1 and R
2 may jointly form a substituted or unsubstituted alicyclic group or aromatic cyclic group), and (2) is known to be used as a synthetic sweetener; Patent Publication No. 7804434 and Belgian Patent No. 2943103 disclose that it is useful as a synthetic intermediate for biosides, etc. (1'1, 11, 4). , of this compound l proboscis, 1/
f' No known use as a proboscis disease control agent 01C
stomach.

[II'l1 Invention, 11pl, Essentials The present inventors have found that it can be used safely and labor-savingly]: It is possible to obtain a real pesticidal effect, and the stable With the aim of finding just one drug that can stimulate the harvest, a large number of compounds were sampled (:)t.
'r'+, "a・? 'i' 71c. In the process,
It has been discovered that a series of oxathiazine derivatives represented by the above formula (11) have an extremely excellent effect on controlling plant insects.

Therefore, the plant disease control agent according to the present invention is represented by the formula (I) and has a small amount of 1h conductor (a) oxathiazine). B) The active ingredient is "C-containing" (1-) as a percentage. 2 n (However, R1 represents a hydrogen atom, a straight chain or branched alkyl group having 1 to 100 carbon atoms, an aliphatic acyl residue, E, or a phenyl group, and R2 represents a hydrogen atom, a straight chain or branched alkyl group having 1 to 10 carbon atoms, ]
1 or a branched alkyl group or a phenyl group.

R1 and R2 are jointly disseminated or compensated for.
Compounds of formula (I) (which may form a double group or an aromatic superposition group) are known, including the above-mentioned bends and methods for their production. Therefore, this compound can be produced by these known methods and any other suitable method.

Specifically, according to the above-mentioned prior art, this compound is produced by, for example, reacting a ketone represented by formula (II) with fluorosulfonyl f-socyanate-1.
-Ketocarboxylic acid amide-N-sulfofluoride J
It can be produced by reacting with l', in the presence of a group, and then closing it.

R' -CH2-00-R2 (old (Ta,, L, R1, R2 represent the same meanings as above)
The oxathiazine derivatives of formula (I) produced by such a production method include the following compounds. tay
However, the present invention is not limited to the following compound examples. In the table, R1 and R2 correspond to formula (I), and the compound numbers shall be referred to in the following experimental examples.

Table 1 Oxathiazine Derivatives The plant disease control agent according to the present invention has an active ingredient represented by the above formula (1).
Except that it should be noted that it is oxathiazine Rh 27% expressed as 41α substance, it is adopted as a disease control agent and 1! J6 Can take any form.

Specifically, one or more of the above oxathiazine derivatives T is diluted as is or with water, solid powder, or other suitable carrier, and if necessary, an auxiliary agent such as a spreading agent is added. or by mixing with various liquid or solid carriers according to the methods commonly used in drug manufacturing, to form the necessary additives such as wetting agents, dispersants, emulsifiers, fixing agents, lubricants, etc. With the addition of adjuvants, we can prepare wettable powders, liquids, powders,
It can be used in the form of 9IjQ preparations such as fine granules. It can also be used as a smoking agent by appropriately blending a combustion agent, a combustion improver, an adjuvant for temperature adjustment, etc.

In producing these preparations, liquid carriers include:
A compound represented by the formula (■) that acts as a solvent or a compound that can be dispersed or melted with an auxiliary agent or the like is used. For example, water, aromatic compounds, hydrocarbons, aliphatic hydrocarbons, halogenated hydrocarbons, alcohols, esters, ethers,
k) Ketones, amides, dimethyl sulfoxide, etc. Solidified materials include clay, kaolin, talc,
Powder of minerals such as diatomaceous earth, bentonite, carbonate, silica, etc., sand and gravel, wood flour, (!'i + fats and other organic powders and granules) can be used.

Examples of the auxiliary agent include nonionic, cationic, anionic, and amphoteric surfactants, gums, fatty acids or salts thereof, polysaccharides, polyalcohols, and the like. As a combustion agent, for example, inorganic nitric acid such as IJum nitrate
←), organic nitrate compounds such as nitrocellulose, perchlorates, various peroxides, etc.

The plant disease control agent of the present invention can be sprayed on the foliage of agricultural and horticultural crops.
) Rui can be used by smoking it, or it can also be used by making it look like a powder coat or by soaking it in a powder coating. Alternatively, it can be applied to crop growing environments such as underwater, soil surface or soil 1"1). In that case, other agricultural and horticultural chemicals such as various fungicides, insecticides,
It can be mixed with herbicides, growth regulators and fertilizers.

When the plant disease control agent of the present invention is used as a liquid agent by spraying it on the stem bore of a horticultural crop, ;ITI %
', Is this compound 'proboscis ft'? 10 to 200 in cloth liquid
It is desirable that it be contained in a concentration of 0TIT (
1. In the case of rich Shosho 11 rifu, aircraft 11 kefu, etc. 2. It can be used as a more concentrated chemical solution if necessary. ), when used as a powder, granule, fine granule, etc., it is desirable to contain 0.17:C to 50 parts, and when used as a smoking agent, it should contain 5 to 75 parts. I want 12.

Application i (type of layer elr for haz j, target crop %1 of 1)
Application to rI species, growth condition [? ``1) Can be changed depending on others. For example, it is used to control rice diseases in paddy fields.
27c to 1Qkg per area, powder etc. 2 per 10ares (・t, tokg, hydrating powder) or emulsion l
It is common to apply 50 to 5,000 times more solution per 10 ar of water at 5 to 200 ml.

There are various plant diseases that should be controlled by the compound of formula (1). Specifically, there are diseases of rice, such as rice blast and leaf blight, and diseases of vegetables, such as gleaming spot 1Y411 t:4i disease, and others.

The compound of formula (I) generally has a low maternal affinity for plants, and as shown in Experiments 1 and 11 below, phytotoxicity was observed.
stomach.

Example 1) Made by Hiroshi 11, [Aqueous phase agent] Compound No. 13 of heavy duty part F, 4゜clay
22 silica earth
30 Polyoxyethylene alkylaryl ether 5 Calcium likunin sulfonate 3 The above ingredients '1! f was uniformly ground and mixed to obtain a wettable powder containing 40 parts of the active ingredient.

Formulation 伜12. [Granules] Lightning; (1 part Compound number 4 compound 10 clay
87 Carpoquin Methylcellulose 3. Mix the above ingredients/7', mix with appropriate amount of water, mold and dry to make granules containing 10 parts of the active ingredient.

Preparation (9113, [emulsion] Heavy M″ compound number 20 compound 20 xylene
30 Dimethylformamide 35 PolyA xyethylene lauryl phenyl ether 10)! Sodium silbenzene sulfonate
Then, an emulsion containing 20% of the active ingredient was prepared.

Town removal example 4. [Powder] τ 4F Part Compound No. 1 Compound 3 Stearin r
Keiki A・Sium 1 hydrated (ilj j
l'f! 1 clay
50 krk
Each of the components listed in Section 45-H was pulverized uniformly at a high magnification to obtain a powder containing active ingredient 3.

2) Medicinal efficacy test sample 1% 7f911 (rice blast control effect test) (
1) Control effect test using foliar spraying method Rice seedlings (variety Nijukoku) with diameters (i, 5 clQ of resin i!12 bots, 8 plants per bot) grown with 4 leaves 1 ml 1] were treated with the above-mentioned product. In the same manner as in Example 1, the aqueous phase agent prepared in Formulation 1 was diluted to a spraying solution with a specific concentration of 11'J, and 40ml per 3 bottles was sprayed using a spray gun.

After air-drying, the rice blast fungus (Pyr) was placed in a greenhouse at 24°C.
icular:1. aOryzae) spores! ll,g
) After spraying Shu71V uniformly and keeping it in contact with F11V and - night humidity, it was transferred to an artificial climate dormitory to induce disease. Seven days after inoculation, the number of disease fM that developed was investigated by the nI number, and the control value was calculated using the following formula.

The results of the test should be as shown in Table 2.

Table 2 Rice blast control effect* by foliar spraying method
J Ijiyaku fi No. 1 contains 1 former IJJ stage 1'11 (Hinozan emulsion (8 bottles 11i special Made by a certain agricultural company ii'+) ') Ibi was used.

(2t: 11'1l15'\ = Control effect test by surface application 50 (1rHyh in 1R Wagner pot of HllJj).

(Using 6 to 7 leaf stage rice transplanted to 3 trees and grown at a water depth of approximately 2 cm, apply 1 pot of granules prepared in the same manner as Example 2 to the surface of the soil. hit fio
It was evenly distributed in mg. f17.7 days after drug application. = In the same manner as in the fabric test, blast fungi were inoculated and infected, and after 7 days, the test was carried out and the control value was determined. The test results are shown in Table 3.

Table 3: ±1 Rice blast control effect by application on the back surface×
July 1 (-The agent contains a commercially available bactericide [Oryzemate agent (
(manufactured by Meiji Seika I3)] was used.

(3) Control effect test by application of Iku C 100 boxes 30 X fi
11 buds and 200 buds in a 3cm x 3cm growing box
G before sowing +'+T L, rice seedlings (variety: Jukoku)
10 days after sowing, the granules prepared in the same manner as in Example 2 of the 11-day preparation were evenly distributed to 30E per box, and the sowing fl'r1
20 days f & (2.5 leaf stage) I cut 1 IC plant to 3 to 5 along with 1 sow on the bed and transplanted it to a Wagner pot with a size of 1/5000 are. Move 1
After 1 month, add rice blast +Y4 in the same way as τ (1), and after +01EI, use the number of lesions as an argument.

The test results are shown in Table 4.

:(!, Table 4: Effect of controlling rice blast disease by applying tf seedling boxes *The above-mentioned Oryzemate granules were used as the control agent.

Test Example 2 [Rice leaf blight control effect H/(test) Diameter 5
, 5 ef seedlings with Cl11 I☆J resin bond,
Using rice seedlings (variety: Jukoku) at the expansion stage, the compounds listed in Table 1 were dissolved in water or (a little R+, acetone, then heated to 41 degrees Celsius for 7 hours) with water. 40m1 per 1 bot of the diluted and prepared Jukusei was poured onto the surface of ±1 audience and treated with the chemical. After the treatment, the seedlings were placed in another container and subjected to flooding conditions. 10 days after the chemical treatment, the top Rice leaf blight fungus (
Xanthomonae campeetrl, sp
V, oryzae) jip suspension was inoculated with a needle, and 28~
Incubate the disease by keeping it in an artificial climate room at 30℃, and contact it with 11fil.
Divide the length of the lesion that appeared on Q Sun Moon by d1 (1 key i 1 nji,
The control value was calculated as 3'1 using the following formula.

The test results are shown in Table 5. As a control agent, a commercially available fungicide [phenazine aqueous agent (manufactured by Meiji Seikaso 3)] containing phenazine-5-oxide as an active ingredient was used and sprayed on the day after inoculation.

Table 5 Test example 3 of rice leaf blight control effect [Cucumber spot bacterial disease control effect test] Konoha No. 2
Using Kirari seedlings (variety: Tokiwa Jiho) with successful leaf development, 10 g of granules prepared in the same manner as in Example 2 were mixed into the soil in the planting hole. (5 stocks in 1 ward, 3
(repetition side).

Five days after planting, the cucumber spot bacterial disease fungus (Psθudomon) was detected.
Aθeyringae pv, lachryman's suspension was sprayed and inoculated, and after 4 weeks, the disease onset level was determined to be O (healthy), 1 (infection surface $'A 1-5 cm), and 2 (sickness level 6-20 cm).
%), 3 (21-50%) and 4 (50 or more staff)
The control value is calculated using the following formula:
I put it out.

The control agent was a commercially available bactericide containing 83% cupric hydroxide as an active ingredient [Kozide Suizagaku (manufactured by Sankonjiku 3)].
1 (100x/fk) was sprayed four times at one week intervals starting the day after planting.

The test results are shown in Table 6.

Table 6 Procedural amendment for effect on control of algal spot fungal disease January/1, 1980 Kazuo Wakasugi, Commissioner of the Patent Office 1, Indication of the case 1982 Patent Application No. 133347 2, Name of the invention Oxathiazine vj Plant disease control agent containing a conductor as an active ingredient 3, relationship with the case of person making corrections! I-, +J applicant (609) Meiji Seito Co., Ltd. 7, the details of the details of the invention, 1! Correct to.

Watazu Before correction After correction

Claims (1)

[Scope of Claims] A plant disease control agent containing at least one oxathiazine derivative represented by the formula (Il) as an active ingredient. 1o represents a straight-chain or branched alkyl group, aliphatic acyl residue], or phenyl group; R2 is a hydrogen atom; 1IS having 1 to 10 carbon atoms;
Represents a 1' or branched alkyl group or a phenyl group. R1 and R2 are jointly 1 to 7 converted or non-lit.
(Also may form an aromatic group or an aromatic J1 group)