JPS6299312A - Agricultural insecticidal and germicidal composition - Google Patents

Abstract

PURPOSE:The titled composition, containing a mostly novel specific nitromethylene derivative and O-ethyl S,S-diphenyl phosphorodithioate and capable of controlling blights and injurious insects of rice plants (blights and planthoppers and leafhoppers of rice plants) at the same time. CONSTITUTION:An agricultural insecticidal and germicidal composition, obtained by incorporating (A) a mostly novel compound (insecticide) expressed by the formula (X is lower alkyl, lower alkoxy or halogen; l is 0, 1 or 2; m is 2 or 3) with (B) O-ethyl S,S-diphenyl phosphorodithioate (controlling agent against blast of rice plants) and, as necessary, further (C) 4,5,6,7-tetrachlorophthalide (controlling agent against blast of rice plants) as active constituents at 1:0.05-20:0.05-20, preferably 1:0.1-10:0.1-10 weight ratio [(A):(B):(C)] by pts.wt., capable of exhibiting improved potentiating and synergistic effect unexpected from effect of the respective independent agents and showing excellent insecticidal and germicidal effect on both blights and injurious insects of rice plants and particularly effective for simultaneous control of the above-mentioned blights and injurious insects and labor saving, etc.

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a novel agricultural insecticide and fungicidal composition which contains a nitromethylene derivative of the formula (Il) and a known fungicidally active compound as active ingredients and exhibits excellent insecticidal and fungicidal activity.

Most of the formula (Il nitromethylene derivatives) used in the present invention are compounds that have not been previously described in publicly known literature, and the compounds and their use as insecticides are disclosed in the prior invention patent application filed in 1983 filed by the same applicant. -72966 and patent application 1982-
It is disclosed in the specification of No. 152945. Moreover, the formula (I
Among l nitromethylene derivatives, compounds where L=Q and their use as insecticides are known and are disclosed in JP-A-60-172976, filed by the same applicant.

Furthermore, it has already been described in Japanese Patent Publication No. 12919/1983 that O-ethyl, S, S-diphenyl, and phosphorosothioate have control activity against rice blast.

However, the action of these active compounds is either an insecticidal effect or a bactericidal effect when used alone, and it is not possible to simultaneously control diseases caused by pathogenic bacteria and damage caused by insect pests.

According to the present inventors, (1) In the general formula, It has been found that a novel active mixture containing a methylene conductor and (2) 0-ethyl, S, S-sophenyl, phosphorosothioate as active ingredients exhibits excellent insecticidal and fungicidal activity.

Conventionally, various pesticides have been developed as agricultural and horticultural insecticides, and have been used as single agents or mixtures. In particular, organophosphorus insecticides and carbamate insecticides are mainly used, and subsequently pyrethroid insecticides have been used. However, although conventional insecticides each have a certain type of insecticidal effect, they differ in their insecticidal spectrum, insecticidal effect (insecticidal effect on various growth stages, such as eggs, larvae, and adult insects), residual effect, and immediate effect. However, they do not fully satisfy various characteristics such as low toxicity, systemic transferability, low toxicity to fish and warm-blooded animals, reduced burial contamination, and reduced number of applications and amount of applied drug.

Furthermore, as a result of the modified use of conventional drugs, various insect pests have emerged that have acquired resistance to them.

In particular, in recent years, planthoppers and leafhoppers (e.g., leafhoppers), which are hemiptera pests, have developed resistance to organophosphorus and carbamate insecticides in rice paddies across Japan, including the warm southwest region. , it has become difficult to control them, and the development of superior drugs is desired.

Furthermore, Kona, which is a vegetable pest that infects aphids, mites, and cruciferous plants, has acquired drug resistance in cotton poleworms and other pests, and it is necessary to control such resistant pests or to treat sensitive pests and resistance. It is desired to develop an excellent drug that can simultaneously control sexual pests.

Father, in recent years, paddy rice cultivation in Japan has been carried out by mechanical transplantation using seedling transplanters. It is desired to develop a drug that does not Furthermore, there is a desire to develop an excellent drug against pests, such as the rice weevil, which have become a particular problem in recent years.

Therefore, important pests of food crops including rice and other insecticides, pests of horticultural crops such as vegetables, flower petals, and fruit trees, pests of craft crops such as tobacco, cotton, and tea, forest pests, and certain types of these pests. It is desired to develop a drug that has even better effects against pests of greenhouse horticulture crops, soil pests such as nematodes, sweat-absorbing and feeding insects such as storage insects, and other glaze pests.

Furthermore, in addition to the development of excellent insecticides as described above, there is a desire to develop insecticides and fungicides that can sometimes control rice blast, planthoppers, and leafhoppers, which are major diseases and pests in rice cultivation.

As a result of intensive research to solve the various problems mentioned above, the present inventors discovered that (2) well-known O-ethyl, S, S-sophenyl, and phosphoroso- The active mixture according to the present invention containing thioate exhibits excellent cooperative and synergistic effects unexpected from the effects of each active compound alone, and exhibits excellent insecticidal and fungicidal effects against rice pests and pests. discovered.

Therefore, the insecticidal and fungicidal composition of the present invention is very effective in the cultivation of agricultural crops, for example, in particular, simultaneous control of pests and labor saving, and is an extremely outstanding technological advance in terms of industrial usefulness. It provides sex.

The nitromethylene conductor of the general formula (Il) used in the active compound mixture according to the invention is defined as follows.

In the formula, X represents a lower alkyl group, a lower alkoxy group or a halogen atom, L represents 0.1 or 2, and m represents 2 or 6, used in the active compound mixture of the present invention. A particularly preferred nitromethylene derivative of the general formula (I) is a compound defined as below and not described in any prior art literature.

In the general formula (Il, X preferably represents a methyl group, methoxy group, chloro atom, bromine atom or fluoro atom, tVil represents 2, 77L represents 2 or 3, and the bond of the pyridine ring The position is 3rd place (father is 5th place).

The nitromethylene derivative of the general formula (Il) can also exist in the form of a salt, such as an inorganic acid salt, a sulfonate, an organic acid salt, a metal salt, etc., preferably, for example, a hydrochloride, a p- Examples include luenesulfonate, cupric acetate, succinate, etc. Therefore, the name used in the present invention includes the nitromethylene derivative of the formula (II) and its salt form. It is.

Used in the active compound mixture according to the invention:
Examples of nitromethylene derivatives of general formula (Il) include the following compounds: 1-(5-pyridylmethyl 1-2- to tromethylene)
Tetrahydropyrimidine, 1-(2-methyl-5-pyridolmethyl 1-2-tromethylene)imidazolidine,
1-(2-Methyl-5-pyridylmethyl 1-2- to tromethylene)tetrahuman C: I2 rimison-1-(2-methoxy-5-pyridylmethyl 1-2- to tromethylene)
Imidazolidine, 1-(2-methoxy-5-pyriturmethy=+-2-tromethylene)tetrahydropyrimidine, 1-(2-chloro-5-pyriturmethyl i-2-
(=) romethylene) imidazolidine, 1-(2-ri c1
0-5-pyritylmethyl)-2-tromethylene)tetrahydropyrimidine, 1-(2-fluoro-5-pyritulmethyl)-2-tromethylene)imidazolidine, 1
-(2-fluoro-5-biriturumethyl 1-2-totromethylene)tetrahydropyrimidine, 1-(2-bromo-5-biriturumethyl)-2-totromethylene)imidazolidine, 1-(2-bromo-5-biriturumethyl 1-
2- Tromethylene) tetrahydropyrimidine, 1-
(5-chloro-2-biriturumethyl 1-2- to tromethylene 1 imidazolisone, 1-(5-chloro-2-biriturumethyl +-2- to tromethylene)tetrahydropyrimidine, 1-(2,4-dichloro-5-birisolimethyl 1) -2-tromethylene)tetrahydropyrimidine,
1-(2,4-dibromo-5-giriturumethyl 1-2-
(tromethylene) imidazolidine, 1-(2,3-fuchloro-5-biriturmethyl l -2-tromethylene)
imidazolidine, 1-(5-biritulmethyl)-2-
(Nido-a-methylene)tetrahydrobiricin-hydrochloride, 1
-(2-Methyl-5-biritylmethyl)-2-totromethylene)tetrahydrobirimicin-P-toluenesulfonate, 1-(2-methoxy-5-pyridylmethyl 1-
2-tromethylene)tetrahydropyrimidine-cono・
phosphoric acid u, 1-(2-chloro-5-&lysylmethyl) -
2-(=)0 methylene 1 imidazolisone-hydrochloride, 1-
(2-Fluoro-5-biriturumethylr-2-totromethylene)tetrahydropyrimidine-cupric acetate salt, 1
-(2-bromo-5-biriturmethyl)-2-tromethylene)imidazolidine-conophosphate, 1-(2,4
-fuchloro-5-biriturmethyl)-2-tromethylene)tetrahydrobyrimidine-p-toluenesulfonate.

One component of the active compound according to the present invention, O-ethyl, S, S-diphenyl, phosphorosothioate (Esofenhonu edifgnphori), is already known as a rice blast control agent (Japanese Patent Publication No. 4412919). 4, which is the other component optionally added,
5.6.7-Titrachlorophthalide (Fthalide ft
hαhactt) is already known as a rice blast control agent (% Publication No. 32592/1983).

In the present invention, the weight ratios of the active compounds of each group in the active compound mixture can vary within a relatively wide range; per part by weight of active compound, (2)
O-ethyl, S, S-sophenyl, phosphorosothioate examples, t 0.05 to 20 parts by weight, preferably 0.1
~10 parts by weight, and when (3) 4.5.6.7-titrachlorophthalide is added, VC contains the component (3), for example, 0.05 to 20 parts by weight, preferably 0.1 ~10 layers can be used.

The active compound mixture according to the invention exhibits excellent insecticidal and fungicidal activity and can be used as an insecticidal fungicide, for example, by foliar spraying, underwater or surface application, soil application, soil mixing treatment, nursery box application.

The active compound mixtures according to the invention exhibit a strong insecticidal and fungicidal action. Therefore, it can be used as an insecticide and fungicide. In addition, the active compound according to the present invention has no phytotoxicity to cultivated plants, has low toxicity to warm-blooded animals, and can accurately control pests, especially insects and diseases, in agriculture and rice protection. can be used for They are usually active against sensitive and resistant species and against all or some growth stages.

Examples of the above-mentioned pests and diseases (diseases and pests) include the following. Examples of such pests include the following.

Insects include Coleoptera pests, such as the rice weevil (
Lizorhoptrtbz oryzophiLu
z l, rice weevil (EchinocirLamtL)
r rqwaytwyl, OwLt
ma oryzaa l; lepidopteran insects, such as C,'hiLo zwpprazza
Pigeon), Kobunomei (Cnαpxαtocrociz)
mecLinaLiz l, Futaobikoyaga (Nαγ
αrL1ααgrutSCεle5), Ichimonso Seseri (
Parnttra gtLttata l ; Hemiptera insects, such as Ntphotgttix cinc
tictpz l, brown planthopper (Nilaparv)
ata ltb, qtnt l, Japanese brown planthopper (La
odtlphax striattLlwo l, SogatgLla fttrcifera
l, green stink bug (Nazara tpp,);
, Locust (Loc-LLsta migratorit)
As a disease, for example, archaeal fungi [ArchirrLyctetes]
r l :), algae [Phycomycetes (Phycomycetes)]
cetti)), Ascomycetes [Ascomycetes (Az
comycttgz l), Basidiomycetes [Basidiomycetes l], Deuteromycetes [FungiImpe
rfectil) and various other plant diseases caused by bacteria.

As a representative example of the bactericidal spectrum of the above-mentioned plant diseases, for example, Pyricularia ory-
Sesame leaf blight fungus (t'ohlioho Lttz rniyabgan), a type of pathogenic bacterium that causes rice ear blight.
Examples include uz 1, but the bactericidal spectrum should not be limited to these.

The active compound mixtures according to the invention can be in the form of a mixture of f1+ and component (2) and optionally component (3), or each can be in the form of customary preparations on their own for extemporaneous mixing. and such forms include solutions, emulsions, suspensions, powders, foams, pastes, granules, aerosols, active compound infiltration - natural and synthetic, microcapsules, seed coatings, preparations with combustion devices. (combustion devices such as fumigation and fume cartridges, guns and coils), and ULV (near mist).
cold rrList l, warm mist (war
rILmi! t l :) can be mentioned.

These formulations can be manufactured by known methods. Such a method comprises, for example, combining the active compound with a vehicle, i.e. a liquid diluent; a liquefied gas diluent; a solid diluent; or a carrier, optionally a surfactant, i.e. an emulsifier and/or a dispersant and/or This can be done by using a foam-forming agent and mixing. When using water as a developing agent, for example, organic solvents can also be used as co-solvents.

Liquid diluents or carriers include, for example, aromatic hydrocarbons (e.g. xylene, toluene, alkylnaphthalenes, etc.), chlorinated aromatic or chlorinated aliphatic hydrocarbons (
For example, chlorobenzenes, ethylene chlorides, methylene chloride, etc.), aliphatic hydrocarbons (e.g., cyclohexane, etc./sorafins (e.g., mineral oil fractions, etc.)), alcohols (e.g., butanol, glycols and their ethers, esters, etc.), ketones (e.g., acetone,
(such as methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone), strongly polar solvents (such as dimethyl formamide, trimethyl sulfoxide, etc.) and water.

Liquefied gas diluents or carriers are gases at room temperature and pressure, examples of which include butane, Delon! gas, nitrogen gas,
Mention may be made of aerosol propellants such as carbon dioxide and/% Cff gunned hydrocarbons.

Solid diluents include soil natural minerals (e.g., kaolin, clay, melk, chalk, quartz, athanoid, montmolinite, diatomaceous earth, etc.), soil synthetic iron materials (e.g., highly dispersed silicic acid, alumina, silica, etc.). salts, etc.).

Solid carriers for granules include crushed and fractionated rocks (e.g. calcite, marble, pumice, sepiolite, dolomite, etc.), synthetic granules of inorganic and organic powders, and fine granules or organic substances ( (e.g. sawdust, coconut shells, corn cobs and tobacco stalks, etc.).

Examples of emulsifiers and/or foaming agents include nonionic and call ethers (e.g., alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates, etc.) and albumin hydrolysis products. I can do it.

Dispersants include, for example, lignin sulfide waste liquor and methylcellulose.

Adhesives can also be used in formulations (powders, granules, emulsions), and such adhesion agents include Cal? Mention may be made of oxymethylcellulose and natural and synthetic polymers such as gum arabic, polyvinyl alcohol and polyvinyl acetate.

Colorants may also be used, including inorganic pigments (such as iron oxide, titanium oxide and Prussian blue), and alizarin dyes, a! Organic dyes such as dyes or metal phthalocyanine dyes and also trace elements such as their salts of iron, manganese, daron, copper, cobalt, molybdenum, zinc may be mentioned.

The formulation contains, for example, 0.1 to 95% by weight of the active ingredient.
, preferably 0.5 to 90% by weight.

The active compound mixtures according to the invention, in their commercially useful formulations and in the use forms prepared by them, may contain other active compounds, such as biocides, fungicides, fungicides, growth regulators or It can also be present as a mixture with herbicides. Here, the above-mentioned insecticides include, for example, organic phosphorus agents, carbamate agents, chlorinated hydrocarbon agents,
Examples include insecticidal substances produced by microorganisms.

Furthermore, the active compound mixtures according to the invention can also be present as admixtures with synergists, and such formulations and usage forms can include those that are commercially useful. The synergist need not be active itself, but is a compound that amplifies the action of the active compound.

The content of the active compound mixtures according to the invention in commercially useful use forms can vary within wide limits.

Temperatures for use of the active compound mixtures according to the invention are, for example, α
00001 to 100 wt'J1%, preferably
o, ooi to 5% by weight.

The active compound mixtures according to the invention can be used in the customary manner adapted to the use form.

Next, the content of the present invention will be specifically explained with reference to Examples.
The present invention should not be limited to this only.

Example 1 (i) Test against brown planthopper Test method: Five rice plants with a plant height of 151 were planted in pots with a diameter of about 15 cm, and 10 days after planting, a pre-prepared water dilution of the active compound at a predetermined concentration was applied using a spray gun. 20I per pot
After air-drying the sprayed chemical solution, the pots were covered with net baskets and 10 4th instar brown planthopper larvae were inoculated per pot.After 5 days, deaths were counted and the insecticidal rate was calculated.

(g) Test method for foliar spray efficacy test against rice blast disease - Paddy rice (variety: Asahi) is cultivated in a clay pot with a diameter of 12σ, and at the 5th to 4th leaf stage, a diluted solution of a predetermined concentration of an active compound prepared in advance is applied to 6 pots. 50rn hit! , dispersed. The next day, a suspension of artificially cultured rice blast fungus spores was spray inoculated (twice), and
The cells were kept in a greenhouse at 100% relative humidity and infected. Seven days after inoculation, the degree of disease per pot was graded and evaluated according to the following criteria, and the control value (%) was determined. At the same time, drug damage was also investigated.

Morbidity Level Lesion area ratio (%) 0.5 2 or less 1 5-5 2 6-10 3 11-20 4 21-40 5 41 or more This test is the result of 6 pots in 1 section.

The results of the tests (i) and (11) are summarized and shown in Table 1.

Note) 1. No phytotoxicity was observed in all the mixtures and single agent uses of Examples 1 (1) and (11).

2. Compound of general formula (I) used in the present invention: 3. Compound used in the present invention: Compound (A): Edifenhonu compound (B) = 7 Salide Example 2 Mixed composition of the present invention in Example IK As a result of using it in a test plot where brown planthopper and rice blast disease occur simultaneously,
The pests were completely controlled at the same time with a control value of 100%.

Procedural amendment May 27, 1988 Michibe Uga, Commissioner of the Patent Office1, Indication of the case, Japanese Patent Application No. 1988-2402372, Name of the invention: Insecticidal and fungicidal composition for agricultural use3, Person making the amendment Related Patent Applicant Address 2-4 Nihonbashi Honmachi, Chuo-ku, Tokyo Name
Japan Special Pesticide Manufacturing Co., Ltd. 4, Agent 107 □! -1! 1...1 5. Date of amendment order Voluntary 6. Subject of amendment 7.1 Ill Correct contents [11 The statement in the "Claims" column of the specification is corrected as follows.

(1) The claims on page 11, line 5 to page 2, line 2 of the specification are amended as follows.

rl, (1) General formula In the formula, X is a lower alkyl group, a lower alkoxy group, or
1 represents a den atom, 1 represents 0, 1 or 2, and 1 represents 2 or 3, an active compound consisting of a nitromethylene derivative of An agricultural insecticidal and fungicidal composition comprising a mixture.

2, 4,5°6 to the active compound mixture of (1) and (2)
．． The agricultural insecticidal composition according to claim 1, which contains 7-titrachloro7thallide.

” [11] The statement in the “Detailed Description of the Invention” column of the specification is corrected as follows.

(1) Specification page 2, 17th to 18th bamboo, page 3, 13th to 1st
Line 4, page 6 lines 6-7, page 10 lines 18-20 and C
/ On page 11, lines 11-12, correct the text [0-ethyl, S, S-diphenyl, phosphorodithioate] to [〇-ethyl S, S-diphenyl phosphorodithioate]. .

(2) On page 5, line 7 of the specification It says “as it is”, Correct it to ``mainly''.

(3) On page 10 of the specification, lines 2-3, rl-(3-pyridylmethyl)-2-tromethylene)
Tetofhydropyridine-hydrochloride” is replaced with “1-(3
-pyridylmethyl)-2-tromethylene)tetrahydropyrimidine-hydrochloride".

(4) On page 10, line 18 of the specification It says "active compound", Correct to "active compound mixture".

(5) On page 16, line 14 of the specification, the phrase [and fine particles or organic substances] is corrected to read [and fine particles of organic substances].

(6) Specification #17, line 7 [It says that adhesive agent J, Correct to "adhesive agent."

(7) On page 118, line 5 of the details. It says [biocide] Correct to "insecticide."

(8) On page 18, line 9 of the specification, after the phrase "chlorinated hydrocarbon drugs," add "carboxylate drugs."

(9) Page 5, No. 7 of the specification It says "temperature is" I corrected myself by saying, “The concentration is.”

(10) On page 19, line 9 of the specification, after the text ``r(i)) Test against brown planthopper,'' a new line is added as follows.

[1!4 of the test compounds Each active compound: 25 to 50 parts by weight Carrier: Mixture of diatomaceous earth and kaolin (1:5)
45 to 70 parts by weight Emulsifier: 5 parts by weight of polyoxyethylene alkyl 72-2 ether And 14! ! do. (11) Table 1 on page 21 of Book #1I is corrected as follows.

(12) In the first line of page 23 of the specification, after the words ``Controlled.'', add a new line as follows.

"Example 3 (hydrating powder) 25 parts of the active compound of formula (1), 25 parts of Niji-7-Konphos,
Mixture of powdered diatomaceous earth and powdered clay (1:5) 45s
, 2 parts of sodium alkylbenzenesulfonate, 3 parts of sodium alkylnaphthalenesulfonate formalin condensate
1 part is ground and mixed to make a wettable powder.

Example 4 (powder)

Claims (1)

[Claims] 1. (1) General formula ▲ Numerical formula, chemical formula, table, etc. ▼ (I) In the formula, X represents a lower alkyl group, a lower alkoxy group, or a halogen atom, and l is 0, 1, or 2 and m is 2 or 3, and an active compound mixture consisting of (2) O-ethyl, S, S diphenyl, phosphorodithioate. Sterilizing composition. 2, 4, 5, 6 in the active compound mixture of (1) and (2)
, 7-tetrachlorophthalide. 7-tetrachlorophthalide.