JPS63154602A - Agricultural and horticultural insecticidal and germicidal composition - Google Patents

Abstract

PURPOSE:To obtain the titled composition, containing an activated compound blend of an imino substituted heterocyclic compound and well-known agricultural and horticultural germicide, e.g. validamycin A, etc., and capable of simultaneous ly controlling blights by blight germs and damage by insect pests without phytotoxicity to cultivated plants. CONSTITUTION:An insecticidal germicidal composition containing an activated compound blend of (A) an imino-substituted heterocyclic compound expressed by the formula [X is S, CH2 or N-R<2> (R<2> is H or alkylcarbonyl); R<1> is pyridyl or thiazolyl; m is 2 or 3; Z is NO2 or CN] with (B) at least one selected from validamycin A (3'-iso-propoxy-2-methylbenzanilide), o-trifluoromethyl-m'- isopropoxybenzanilide and 6-(3,5-dichloro-4-methylphenyl)-3(2H)pyridazinone as active ingredients. The ratio of the active ingredients in combination is preferably 0.01-10pts.wt. ingredient (B) based on 1pts.wt. ingredient (A).

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention provides a novel agricultural insecticidal and fungicidal composition which contains an imino-substituted heterocyclic compound of formula (1) below and a known fungicidal active compound as active ingredients and exhibits excellent insecticidal and bactericidal activity. relating to things.

The imino-substituted heterocyclic compounds of formula (1) used in the present invention and their use as insecticides are disclosed in Japanese Patent Application No. 60-106
No. 854, Japanese Patent Application No. 1982-219082 and Japanese Patent Application No. 1983
．． -4862.9.

Furthermore, it has already been described that the following drugs have bactericidal activity for agricultural and horticultural purposes. For example, validamycin A, 3'-
iso-propoxy-2-methylbenzanilide% o
-t, +J Fluoromethyl-ω'-isopropoquine benzoic acid anilide, 6-(3,5-cyclo-4-methylphenyl)-3(2H) pyridazinone (Bestayside v = Yual 7th edition 1983 The B r
itishCrop Protection Co.
published by unci1).

However, the effect 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, A pyridyl group (the substituent represents at least one selected from a halogen atom or an alkyl group) or an optionally substituted thiazolyl group (the substituent represents at least one selected from a halogen atom or an alkyl group) ), m is 2
or 3, and Z represents No2 or CNt-, and (2) validamycin As 3'-iso-propoxy-2-methylbenzanilide, 0-trifluoromethyl 1'-isopropoxy Benzoic acid anilide and 6-(3,
It has been found that a novel active compound mixture containing as active ingredient at least one compound selected from 5-cyclo-4-methylphenyl)-3(2H)pyridazinone exhibits excellent insecticidal and fungicidal activity.

Conventionally, various pesticides have been developed as insecticides for gardening, and have been used as single agents or mixtures. Organophosphorus insecticides and carbamate insecticides are mainly used for Vf, 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, various properties such as low toxicity, systemic transferability, low toxicity to fish and bleeding animals, reduction in environmental pollution, and reduction in the number of applications and the amount of applied drug are not fully satisfied.

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

In particular, in recent years, hemiptera pests such as planthoppers and leafhoppers (e.g., leafhoppers) that have acquired resistance to organophosphorus insecticides and carbamate insecticides have appeared in rice fields in various parts of Japan, including the warm southwest region. It is becoming difficult to control them, and the development of superior drugs is desired. Furthermore, pests such as the diamondback moth and cotton ballworm, which are vegetable pests that injure aphids, mites, crucifers, and vegetables, have acquired drug resistance, and it is now necessary to control such resistant pests or to counteract them with susceptible pests. It is desired to develop an excellent drug that can simultaneously control sexual pests.

In addition, in recent years, paddy rice cultivation in Japan has mainly been carried out by mechanical transplantation using seedling transplanters, and in addition to pest control in paddy rice cultivation, excellent and non-toxic chemicals are needed to control pests by applying seedling boxes. development is desired. 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 grains, 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 facilities among these are important pests. It is desired to develop a drug that has even better effects against pests of horticultural crops, soil pests such as nematodes, sweat-absorbing and feeding insects such as stored grain pests, and other various pests.

Furthermore, in addition to the development of excellent insecticides as mentioned above, the development of insecticides and fungicides that can simultaneously control rice blast, planthoppers, leafhoppers, and pests of rapeseed and fruit trees, which are major diseases and pests in rice cultivation. is desired.

As a result of intensive research aimed at solving the various problems described above, the present inventors surprisingly discovered the present invention, which combines (1) an imino-substituted heterocyclic compound with (2) a known agricultural and horticultural fungicide. It has been discovered that a mixture of active compounds according to the present invention exhibits a broad spectrum of effects that cannot be achieved by the effects of each active compound alone, and exhibits excellent insecticidal and fungicidal effects against rice diseases and insect pests.

Therefore, the insecticidal and fungicidal composition of the present invention is very effective in the cultivation of agricultural and horticultural crops, for example, in simultaneous control of pests and labor saving, and has extremely outstanding industrial utility. It provides technological inventive step.

The imino-substituted heterocyclic compounds of the general formula (I) used in the active substance combinations according to the invention are defined as 6 in which Xi! S, CH, or 1iN-R" (in the formula, R2 represents a hydrogen atom or an alkylcarbonyl group), and R1 is an optionally substituted pyridyl group (the substituent is selected from a halogen atom or an alkyl group). represents an optionally substituted thiazolyl group (the substituent represents at least one selected from a halogen atom or an alkyl group), and m is 2.
or 3, and Z represents N O2 or CN.

In the general formula (I), preferably, X represents S, CH2 or N-R2 (in the formula, R2 represents a hydrogen atom or an alkylcarbonyl group having 1 to 3 carbon atoms of an alkyl group), and R+ represents a pyridyl group substituted with one or two selected from a chloro atom, a bromine atom, a fluoro atom, or a methyl group, or a thiazolyl group substituted with a chloro atom, a fluoro atom, a bromine atom, or a methyl group, and a pyridine ring The bonding position of is the 3-position (or 5-position), the bonding position of the thiazole ring is the 5-position, and - is the 2-position.
or 3, and Z represents NO2 or CN.

As examples of imino-substituted heterocyclic compounds of general formula (1) used in the active substance combinations according to the invention, mention may be made of the following compounds:

1-(3-pyridylmethyl)-2-troimino)imidazolidine, 1-(2-chloro-5-pyridylmethyl)-2-troimino)imidazolidine, 1-(2-chloro-5-pyrimidylmethyl)- 2-troimino)tetrahydropyrimidine, 1-(2-fluoro-5-pyridylmethyl)-2-troimino)imidazolidine, 1-(2-fluoro-5-pyridylmethyl)-2-troimino)tetrahydropyrimidine, 1-(2-bromo-5-pyridylmethyl)-2-troimino)imidazolidine, 1-(2,3-dichloro-5-bilinormethyl)-2-
troimino)imidazolidine, 1-(2-methyl-5-pyridylmethyl)-2-troimino)imidazolidine, 1-(2-methyl-5-pyridylmethyl)-2-troimino)tetrahydropyrimidine, 1- (2-chloro-5-thiazolylmethyl)-2-troimino)imidazolidine, 1-(2-chloro-5-thiazolylmethyl)-2-troimino)tetrahydropyrimidine, 1-(2-fluoro-5-thiazolylmethyl)- 2-troimino)imidazolidine, 1-(2-methyl-5-thiazolylmethyl)-2-troimino)imidazolidine, 1-(2-methyl-5-thiazolylmethyl)-2-troimino)tetrahydropyrimidine, 1- Acetyl-3
-(2-chloro-5-pyridylmethyl)-2-troimino)imidazolidine, 1-acetyl-3-(2-chloro-5-pyridylmethyl)-2-troimino)tetrahydropyrimidine, 1-butyryl-3- (2-chloro-
4-fluoro-5-pyridylmethyl)-2-troimino)imidazolidine, 3-(2-chloro-5-pyridylmethyl)-2-troimino)thiazolidine, 3-(2-chloro-5-pyridylmethyl) -2-totroimino)tetrahydro-2H-1,3-thiazine, 3-
(2-Fluoro-5-pyridylmethyl)-2-troimino)thiazolinone, 1-(2-chloro-5-pyridylmethyl)-2-troimino)pyrrolidine, 1-(2-chloro-5-pyridylmethyl) -2-troimino)piperidine, 1-(2-bromo-5-pyridylmethyl)-2-troimino)pyrrolidine, 1-(2-fluoro-5-pyridylmethyl)-2-troimino)pyrrolidine, 1- (2-chloro-5-pyridylmethyl)-2-(cya/imino)imidazolidine, 1-(2-chloro-5-pyridylmethyl)-2-(cyanoimino)tetrahydropyrimidine, 1-(2-fluoro-5 -pyridylmethyl)-2-(cyanoimino)imidazolidine, 1-(2-bromo-5-pyridylmethyl)-2-(cya/imino)imidazolidine, 1-(2-methyl-5-pyridylmethyl)-2 -(cya/imino)imidazolidine, 1-(2-methyl-5-pyridylmethyl)-2-(cyanoimi/)tetrahydropyrimidine, 1-(2-chloro-5-thiazolylmethyl)-2-(cyanoimino)imidazolidine , 1-(2-chloro-5-thiazolylmethyl)-2-(cyanoimino)tetrahydropyrimidine, 1-(2-fluoro-5-thiazolylmethyl)-2-(cyanoimino)
Tetrahydropyrimidine, 1-(2-chloro-5-pyridylmethyl)-2-(cyanoimino)thiazolidine, 1l-1-(2-chloro-5-pyridylmethyl)-2-(cyanoimino)tetrahydro-2H-1t3-thiazine ,1
-(2-fluoro-5-pyridylmethyl)-2-(cyanoimino)thiazolidine, 1-(2-chloro-5-thiazolylmethyl)-2-(cyanoimino)thiapridine, 1-(2-chloro-5-thiazolylmethyl)- 2-(cyanoimino)tetrahydro-2H-1,3-thiazine.

One of the fungicidal active substances used in the active substance combination according to the invention is represented by the formula below.

3'-iso-propoxy-2-methylbenzanilide (
mepronil) 0-triple olomethyl-isopropoxybenzoic acid anilide (flutolanil) 6
-(3,5-dichloro-4-methylphenyl)-3(2
H) Pyridazinone The abovementioned fungicidal compounds which are one component of the active compound mixture according to the invention are already known. That is, for example, The Pe5tside Manual.
Manual) 7th edition 1983 (The Br1t
ish Crop protection C
It has already been described as a bactericidal agent in the following publications (published by Unci 1) and is well known.

In the present invention, the weight ratios of the active compounds of each group in the active substance combination can vary within a relatively wide range, generally (1) the activity of the imino-substituted bicyclic compound of general formula (I); per part by weight of active compound of the group of compounds (
2) active compounds of the active compound group of fungicides, e.g. 0.0
It can be used in an amount of 5 to 20 parts by weight, preferably 0.1 to 10 parts by weight.

The active substance combination 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, stomach seedling box application, etc.

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

The above-mentioned pests (diseases and pests) include, for example, the following: Examples of such pests include the following.

Insects include Coleoptera pests, such as the bean weevil (Callosobrucbus c).
binensis), brown weevil (S 1topbi
lus zeamais), Brown Strawberry (Tr.
ibolium castaneuIll), Japanese ladybird (Epilachna virgin)
tioctomaculata), A griotes fuscieol I
is), Anomala rufocu
prea) 1 Colorado Boted Beetle (Leptin)
otarsa deceIllineata), Sheabrotica spp+
, Monocha IIlus
alternatus), rice weevil (L 1
ssorl+optrus oryzoph'i'1
us) S rice weevil (E ehionocinemu)
s squareeus), rice weevil (Oul
e+sa oryzae), Hirataki beetle (L
yctus bruneus): Lepidoptera, e.g. Lysantria dispar.
, Malacosoma neustr.
ia), P 1erisrapae, S podoptera l 1tur
a), Armyworm (Mamestra brassica)
e), Chilo 5upres
salis), Cobb/May W (Cnaphalocr
oeis medinalis), 7 Taobikoya! f
(NaraBa aenescens), Pyrausta nubilalis, Ephestia cautell
a), A doxophyes
orana), robin)y (Carpoeapsa)
pomonella), Capraiga (Agr.

tis fucosa), honey ff (Ga!Ie
ria uellonella), Kona 1F (Plu
tella maculipennis), He!1othis virescens,
Orange leafminer ff (Phyllocnistis)
eitrella), Parnar
a guttata); half-titled insects, such as "7 v guro"J':It<i (Nephotetti)
x cinctieps), brown planthopper (N.
1 laparvata lugens), brown-bottomed planthopper (Laodelphax 5 triatellu
s)
reifera), Quercus spp. (P 5eu)
docoecus eomstoeki), Ya/nekai laminae (U n+zspis yanonens
is) S peach 7 aphid (Myzus pers)
ieae), apple aphid (Aphis pom)
i), cotton aphid (A phis gossyp)
ii), Japanese radish aphid (Rhopalosi)
phu16pseudobrassicas), S tephanitis nashi,
Green stink bug (Nazara s9p*), T realeurodes va
porariorum), pylori (P syl Ia
spp, L orthoptera, e.g. Gryl 1otalpa african
a) Locust migrator
ia *igratoriodes); as a disease, for example, the archaeal fungus E archimyetetes
)], P hyeomycetes
es)], the child's cane [Ascomycetes (A scomy
eetes)], Basidiomycetes [Basidiomycetes]
idiomycetgs), Mycobacterium deuteromycets
This concludes with a list of various plant diseases caused by fungi and other fungi.

As a representative example of the bactericidal spectrum of the above plant diseases, for example, rice sheath blight @1i (Pellicularia 5
asakii), and Rhizoctonia solani, a type of pathogenic fungus that causes vegetable seedling blight.
5olani), but the bactericidal spectrum should not be limited to these.

The active substance combinations according to the invention can be in the form of a mixture of components (1) and (2) or each can be in the form of customary preparations individually for extemporaneous mixing. Such forms include solutions, emulsions, breath preparations, powders, foams, pastes, granules, aerosols, active compound infiltration - natural and synthetic, microcapsules, seed coatings, preparations with combustion devices ( Combustion devices include, for example, fumigation and fume cartridges, guns and coils), as well as ULV [cold mist, warm mist].

These formulations can be manufactured by known methods. Such methods include, for example, dispensing the active compound with a widening agent, i.e., a liquid diluent; a liquefying vehicle; a solid vehicle; or a carrier, optionally a surfactant, i.e., an emulsifying agent and/or a dispersing agent. This can be done in addition to mixing using agents and/or foam formers. When using water as extender, 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., paraffins (e.g., mineral oil fractions, etc.)], alcohols (e.g., butyl, glycols, and their (ethers, esters, etc.), ketones (eg, acetone, methyl ethyl ketone, chlorohexanone, etc.), strongly polar solvents (eg, dimethylformamide, dimethyl sulfoxide, etc.) and water.

Liquefied gas diluents or carriers are gases at room temperature and pressure, examples of which include butane, propane, nitrogen gas, carbon dioxide, and aerosol propellants such as halogenated hydrocarbons. .

Solid diluents include soil natural minerals (e.g. kaolin, clay, talc, chalk, quartz, acpal guide,
montmorinite, diatomaceous earth, etc.), and soil synthetic minerals (for example, highly dispersed silicic acid, alumina, silicates, etc.).

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

Examples of emulsifiers and/or foaming agents include nonionic and anionic emulsifiers [e.g., polyoxyethylene fatty acid esters, polyoxyethylene fatty acid alcohol ethers (
For example, alkylaryl polyglycol ethers,
Alkyl sulfonates, alkyl sulfates, arylsulfonates, etc.) 1, albumin hydrolysis products.

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

Fixing agents can also be used in the formulations (powders, granules, emulsions), such fixing agents include carboxymethylcellulose and natural and synthetic polymers such as gum arabic, polyvinyl alcohol and polyvinyl acetate. I can do it.

Coloring agents may also be used, such as amorphous pigments such as iron oxide, titanium oxide and Prussian blue, and organic dyes such as alizarin dyes, azo dyes or gold i7 talocyanine dyes, and also Mention may be made of such trace elements as their salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.

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

The active substance combinations according to the invention, in their commercially useful formulations and in the use forms prepared by them, may also contain other active compounds, such as insecticides, fungicides, fungicides, biocontrol agents. Alternatively, it may be present as a mixture with a herbicide. Here, examples of the above-mentioned insecticides include fi+7 agents, carbamate agents, chlorinated hydrocarbon agents, carboxylate agents, and insecticidal substances produced from microorganisms.

Furthermore, the active substance combinations according to the invention can also be present as admixtures with synergists; 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.

The working concentrations of the active compound mixtures according to the invention are, for example, o
, o o o o i - 100% by weight, preferably o, ooi - 5% by weight.

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

When used against stored pests, the active compound is
Due to its good stability against alkalis on lime materials, as well as its excellent residual effect on wood and soil,
It is highlighted.

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

Example 1 (i) Preparation of test compounds against brown planthopper Each active compound: 25 parts by weight Carrier: 70 parts by weight of a mixture of diatomaceous earth and kaolin (1:5) Emulsifier: 5 parts by weight of polyoxyethylene alkylphenyl ether As described above Amounts of the active compound, carrier and emulsifier are pulverized and mixed to form each water use agent, and a predetermined amount of the drug is diluted with water and mixed to produce WR.

Test method: Three rice plants of Hayashi (approximately 15cm) were planted in pots with a diameter of approximately 130cm, and 10 days after planting, a pre-prepared water dilution of the active compound at a predetermined concentration was applied to a pot of 20m per pot using a spray gun.
j! After spraying and 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 3 days, the dead insects were counted and the killing rate was calculated.

(ii) Test method for testing the control effect on rice sheath blight: Paddy rice (quality: Jinnanfeng) is cultivated in a 1A15,000 Wagner pot under water, and during the panicle formation stage, the active compound prepared in advance is diluted to a predetermined concentration. liquid, 100 per 3 bots
Sprayed at a rate of ml.

The day after spraying, the base of the test rice plants was sprayed with barley medium for 10 minutes.
The sheath blight fungus that had been cultured for several days to form sclerotia was inoculated, and the temperature was increased to 2.
The seeds were kept in a greenhouse at 8-30°C and a relative humidity of 95% or higher for 10 days to allow them to develop, and then the degree of disease onset and the presence or absence of phytotoxicity were investigated. In the investigation, the degree of damage was expressed based on the following criteria based on the growth of lesions from the inoculated area of the plant, and the control value was determined.

N However, N: Total number of investigated bases no: s Number of diseased bases nI: Number of diseased bases up to the first leaf sheath (from the bottom) 02:
Number of radix affected up to the second leaf sheath (from the bottom) n3: Number of radix affected up to the $3 leaf sheath (from the bottom) The results of the above tests (i) and (ii) are summarized below.

Note 1: No phytotoxicity was observed in all the mixtures and single agent uses of Example 1 (i) and (ii).

2. Compound of general formula (1) used in the present invention: Compound N
o, 1 1-(2-chloro-5-pyridylmethyl)-2
-troimino)imidazolidine, Compound No. 2 1-(2-chloro-5-pyridylmethyl)-2-troimino)tetrahydropyrimidine, Compound No. 3 1-(2-chloro-5-thiazolylmethyl)-2- Compound No. 4 1-7 cetyl-3-(2-chloro-5
-pyridylmethyl)-2-toimino) imidazolidine, metal compound No. 5 3-(2-chloro-pyridylmethyl)
-2-troimino)thiazolidine, Compound No. 6 1-(2-chloro-5-pyridylmethyl)-2-troimino)piperidine, Compound No. 7 1-(2-chloro-5-pyridylmethyl).

-2-(nafimino)imidazolino hmm.

3. Compounds used in the present invention: Compound (A): Varigumycin A Compound (B): Flutolanil (trade name: Moncat) Example 2 The mixed composition of the present invention in Example 1 was used to treat brown planthopper and rice sheath blight. As a result of using it in a test area where
The pests were completely and simultaneously controlled with a control value of 100%.

Example 3 (Irrigation agent) 25 parts of the active compound of formula (1), 25 parts of flutolanil, 45 parts of a mixture of powdered diatomaceous earth and powdered clay (1:5),
2 parts of sodium alkylbenzene sulfonate and 3 parts of sodium alkylnaphthalene sulfonate formalin condensate are ground and mixed to obtain an irrigation agent.

Example 4 (powder) 1 part of the active compound of formula (1), 1.5 parts of flutolanil, and 97.5 parts of powdered clay were ground and mixed to form a powder and one other person.

Claims (1)

[Claims] 1. (1) General formula ▲ Numerical formula, chemical formula, table, etc. ▼ (I) In the formula, X is S, CH_2 or N-R^2 (in the formula, R^2
represents a hydrogen atom or an alkylcarbonyl group), and R^1 represents an optionally substituted pyridyl group (the substituent represents at least one selected from a halogen atom or an alkyl group) or a substituted is a thiazolyl group (the substituent represents at least one selected from a halogen atom or an alkyl group), m represents 2 or 3, and Z represents NO_2 or CN, an imino-substituted heterocycle of Formula compound and (2) validamycin A, 3'-iso-propoxy-
2-Methylbenzanilide, o-trifluoromethyl-
m'-isopropoxybenzoic acid anilide and 6-(3,
An insecticidal and fungicidal composition for agricultural and horticultural use, characterized in that it contains a mixture of active compounds with at least one selected from 5-dichloro-4-methylphenyl)-3(2H)pyridazinone.