JPS63126810A - Agricultural and horticultural insecticide composition - Google Patents

Abstract

PURPOSE:To obtain the titled composition showing synergistically controlling effects on insects pests in paddy fields and agricultural and horticultural insect pests, containing both a specific imino-substituted heterocyclic compound and an organic phosphoric ester. CONSTITUTION:The titled composition containing a compound [e.g. 1-(3- pyridylmethyl)-2-(nitroimino)imidazolidine, etc.] shown by formula I [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] and a compound shown by formula II (X<1> is O or S; X<2> is O or S or direct bond of P and R<3>; R<1> is lower alkyl; R<2> is lower alkoxy, phenyl, etc.; R<3> is lower alkyl, lower alkenyl, phenyl, etc.) in a weight ratio of 1:0.1-5. The composition has neither phytotoxicity nor toxicity and can exterminate insect pests such as Chilo suppressalid Walker, diamondback moth, cockroach, etc.

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a novel agricultural and horticultural active substance combination having an excellent insecticidal effect of an imino-substituted polycyclic compound of formula (1) below and a known organic phosphate ester.

The imino-substituted polycyclic 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
-48629.

Furthermore, it has already been described that the following organic phosphate esters have insecticidal activity. For example, 〇-2,4-dichlorophenyl 〇-ethyl S-7'ropylphosphorodithioe), 0.0-diethyl 0-5-phenylisoxazol-3-yl phosphorothiony), 2,3-dihydro- 3-oxo-2-72-6-biligdinyl
Noethyl phosphorothionate, 0,0-diethyl 5-
2-Ethylthioethyl phosphorothionate, etc. [See, for example, the Vesticide Manual (7th edition 1983, The Br1tish Crop Prot
However, the action of these known organophosphate esters is not always satisfactory, especially when the concentration of active compound is low and when only small amounts are applied. Furthermore, as a result of using these insecticides over several years, some pests have acquired resistance, making it extremely difficult to control them.

According to the present inventors, (1) In the general formula, X i! S%CH, or N-R2 (wherein R2
represents a hydrogen atom or an alkylcarbonyl group), and R1 represents an optionally substituted bilinol group (the substituent represents at least one selected from a halogen atom or an alkyl group) or an optionally substituted bilinol group. It represents a thiazolyl group (the substituent represents at least one selected from a halogen atom or an allyl group), and the theory is 2.
or 3, and Z represents NO2 or CN, and (2) the general formula x2 is an oxygen atom, a sulfur atom, or a phosphorus atom in the formula and R
3, R1 represents a lower alkyl group, R2 represents a lower alkoxy group, lower alkylthio group, lower alkylcarbonyl 7mido group, or phenyl group, R3 represents a substituted or unsubstituted lower alkyl group, lower At least one compound selected from organic phosphoric acid esters represented by: an alkenyl group, a phenyl group, or a heteroaryl group, or R2 and R3 together represent a phosphorine ring together with the phosphorus atom and X2 in the formula; It has been found that a new active substance combination containing as an active ingredient exhibits excellent insecticidal 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 properties such as low toxicity, systemic transferability, low toxicity to fish and warm-blooded animals, reduced environmental pollution, and reduced number of applications and amount of applied drugs.

Furthermore, as a result of the conventional use of chemicals, various pests have emerged that have acquired resistance to various chemicals. In particular, in recent years, planthopper leafhoppers (e.g., leafhoppers), which are hemipteran pests that have acquired resistance to organophosphorus insecticides and carbamate insecticides, have appeared in rice fields in various areas including the warm southwest region of Japan. It is becoming difficult to control the disease, and the development of superior drugs is desired. Furthermore, pests such as aphids, mites, crucian crucian carp, and cotton ballworm, which are vegetable pests that infect cruciferous vegetables, have acquired drug resistance, and it is necessary to control such resistant pests or to treat sensitive pests and resistance. It is desired to develop a 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. There is a desire to develop a drug that has even more excellent effects on horticultural crop pests, soil pests such as nematodes, sweat-absorbing and feeding insects such as field pests, and other various pests.

As a result of intensive research to solve the various problems described above, the present inventors surprisingly discovered that the imino-substituted polycyclic compound represented by the above formula (1) does not contain the well-known compound represented by the above formula (n). It has now been discovered that the insecticidal activity of the active compound mixture according to the invention containing organic phosphate esters is greater than the sum of the effects of each active compound alone, exhibiting an excellent cooperative and synergistic effect.

That is, by applying the insecticidal composition according to the present invention,
For example, rice field pests, such as lepidopteran pests.
and effects on pests of horticultural crops such as fruit trees and vegetable crops, such as crucian carp (Lepidoptera) and aphids (Hemiptera), can be achieved cooperatively and synergistically at lower concentrations than when using only a single active compound. I found out.

Therefore, the insecticidal composition of the present invention is very effective in the cultivation of agricultural and horticultural crops, and provides extremely outstanding technological progress in terms of industrial usefulness.

The imino-substituted heterocyclic compounds of general formula (1) used in the active substance combinations according to the invention are defined as follows.

In the formula, or an alkyl group) or an optionally substituted thiazolyl group (the substituent is a halogen atom or an alkyl group; Appendix I! Me 7.) 1) One 6-l shim (in Japanese) Fuyuo hl-1 represents 2 or 3, and Z represents NO2 or CN.

In the general formula (1), preferably, R- represents a pyrinol group substituted with one or two selected from chloro atom, bromine atom, fluoro atom, or methyl group, or a thiazolyl group substituted with chloro atom, fluoro atom, bromine atom, or methyl group; , and the bonding position of the pyridine ring is the 3-position (or 5-position), the bonding position of the thiazole ring is the 5-position, - represents 2 or 3, and Z represents NOx or CN.

Examples of imino-substituted polycyclic compounds of the general formula (() used in the active substance combinations according to the invention include the following compounds:

1-(3-pyridylmethyl)-2-(ditorimino)imidazolidine, 1-(2-chloro-5-pyridylmethyl)-2-troimino)imidazolidine, 1-(2-chloro-5-pyridylmethyl) )-2-totroimino)tetrahydropyrimidine, 1-(2-fluoro-5-pyridylmethyl)-2-totroimino)imidazolidine, 1-(2-fluoro-5-pyridylmethyl)-2-totroimino)tetrahydro Pyrimidine, 1-(2-promo-5-pyridylmethyl)-2-totroimino)imidazolidine, 1-(2,3-dichloro-5-bilinormethyl)-2-
nitroimino)imidazolidine, 1-(2-methyl-5
-pyridylmethyl)-2-troimino)imidazolidine, 1-(2-methyl-5-bilinormethyl)-2-troimino)tetofhydropyrimicine, 1-(2-chloro-5
-thiazolylmethyl)-2-troimino)imidazolidine, 1-(2-chloro-5-thiazolylmethyl)-2-troimino)tetrahydropyrimidine, 1-(2-fluoro-5-thiazolylmethyl)-2-troimino)imidazo Lysine, 1-(2-methyl-5-thiazolylmethyl)-2-to-troimino)imidazolidine, 1-(2-methyl-5-thiazolylmethyl)-2-to-troimino)tetrahydropyridine, 1-7cetyl-3-
(2-chloro-5-bilinormethyl)-2-troimino)imidazolidine, 1-acetyl-3-(2-chloro-5-bilinormethyl)-2-troimino)tetrahydropyridicune, 1-butyryl-3- (2-chloro-4-fluoro-5-
pyridylmethyl)-2-troimino)imidazolidine, 3-(2-chloro-5-bilinormethyl)-2-(nitroimino)thiazolidine, 3-(2-chloro-5-pyridylmethyl)-2-troimino)7 Trahydro2H-1,3-thiazine, 3-(2-fluoro-5-pyridylmethyl)-2-troimino)thiazolidine, 1-(2-5-pyridylmethyl)-2-troimino)pyrrolidine , 1-(2-chloro-5-pyridylmethyl)-2-nitroimino)piperidine, 1-(2-promo-5-pyridylmethyl)-2-nitroimino)pyrrolidine, 1-(2-fluoro-5-pyridyl) methyl)-2-toimino)pyrrolidine, 1-(2-chloro-5-pyridylmethyl)-2-(cyanoimino)imidazolidine, 1-(2-chloro-5-pyridylmethyl)-2-(cyanoimino)tetrahydro Pyrimidine, 1-(2-yluoly-5-pyridylmethyl)-2-(cyanoimino)imidazolidine, 1-(2-promo-5-pyridylmethyl)-2-(cyanoimino)imidazolidine, 1-(2-methyl -5-pyridylmethyl)-2-(cyanoimino)imidazolidine, 1-(2-methyl-5-bilinormethyl)-2-(cyanoimino)tetrahydropyrimidine, 1-(2-chloro-5-thiazolylmethyl)-2-( cyanoimino)imidazolinone, 1-(2-chloro-5-thiazolylmethyl)-2-(cyanoimino)tetrahydropyrimidine, 1-(2-fluoro-5-thiazolylmethyl)-2-(cyanoimino)
Tetrahydropyrimidine, 1-(2-chloro-5-pyridylmethyl)-2-(cyanoimino)thiazolidine, 1-(2-chloroo-5-pyridylmethyl)-2-(cyanoimino)tetrahydro-2H-1,3- Thiazine, 1-(2-fluoro-5-pyridylmethyl)-2-(cyanoimino)thiazolidine, 1-(2-chloro-5-thiazolylmethyl)-2-(cyanoimino)thiazolidine, 1-(2-chloro-5- Thiazolylmethyl)-2-(cyanoimino)tetrahydro-28-1,3-thiazine.

The compounds used in the active substance combination according to the invention
i 17 Phosphate esters have the general formula
3, R1 represents a lower alkyl group, R2 represents a lower alkoxy group, lower furkylthio group, lower furkylcarbonyl 7mido group or 7enyl group, R3 represents a substituted or unsubstituted lower It represents an alkyl group, a lower alkenyl group, a phenyl group or a heteroaryl group, or R2 and R3 together represent a phosphorine ring together with the phosphorus atom and X2 in the formula.

In the general formula (If), preferably 1 (1 represents an alkyl group having 1 to 4 carbon atoms, and R2 is an alkoxy group, an alkylthio group, an alkylcarbonylamide group, or a 7-ethyl group each having 1 to 4 carbon atoms) R3 represents a halogen atom, a phenyl group substituted with one or two selected from methyl, methylthio, nitro, and cyano groups, or R3 is optionally a halogen atom or a carbon atom number of 2 to 3 Flukylthio (or sulfinyl) group, phenyl group, flukoxy carbonyl group having 1 to 4 carbon atoms, 1 carbon atom
Alkylcarbamoyl group having 1 to 4 carbon atoms, 1 to 4 carbon atoms
a furkylcarbamethylalkyl (C+~2) thioalkyl (C+~2) group, N-C1-C3 alkyl optionally substituted with a C1-C4 flucoquinyl-N-methylcarbamoyl group; 1 to 2 carbon atoms substituted with a halogen-substituted benzoxazole group, or a halogen atom and a 7-talimide group
represents an alkyl group of 2 to 3 carbon atoms, or R3 represents an alkenyl group having 2 to 3 carbon atoms substituted with 1 or 2 of a halogen atom, a halogen-substituted phenyl group, or an alkylcarbamoyl group, or R3 represents 1 to 3 of the same or different Pyridinyl, pyrimidinyl, pyridacyl, quinoxalinyl, inxazolyl or oxo-1,3,4- which may be substituted with three alkyl groups each having 1 to 4 carbon atoms, an alkoxy group, a noalkylami7 group, a halogen, a phenyl group represents a cyanoazolyl group, or R2 and R3 together represent a penzoquoxaphosphorine ring together with the phosphorus atom and x2 in the formula, or when x2 represents the immediate bond between the phosphorus atom and R3, R3 represents a group - Particular preference is given to H 2 organophosphates, representing cHccl s.

The following compounds may be mentioned: 0.0-Dinotyl 0-4-methylthiotolyl phosphorothioate (7-enthion)
, 0, O-methyl 0-4-nitro-trilyl phosphorothioate (fenitrothion feniLrot
bion) % 4-(Methylthio)7-El Nobrovir Phosphate (propapbs), 0-4-cyanophenyl 0.0-methyl phosphorothioate (cyanophos), 0-2.4-dichlorophenyl 0-ethyl S-propyl phosphoro Dithioate (prothiofos), 〇-ethyl 0-4-methylthiophenyl S-provil phosphorodithioate (sulprofos 5ulpro
fos), 0-4-bromo-2-chlorophenyl 〇-enal S
-Propyl phosphorothioate (profenophos p
rofenofos) S n-dihandle 0-4-nitrophenyl phenylphosphonothioate (EPN), 0-4-cyanophenyl 〇-ethyl 7-ethyl phosphonothioate (cyano 7-enphos cyanorenp)
hos), 0, S-dimethyl acetylphosphoramitothioni -
(a 7 nee to aeephate)
, 5-2-ethylsulfinyl-1-methyldityl 0
, O-dimethyl phosphorothioate (oxydeprofos), 0.0-methyl 5
-2-Ethylthioethyl phosphoronothioate (disulfoton), 5-2-ethylthioethyl 0.0-methylphosphorodithioate (thiometon), 5-a-ethoxycarbonylbenzyl 0,0-methyl Phosphorodithioate (pbenthoate), S-1,2-bis(ethoxycarbonyl)ethyl 0°0
-Methinol phosphorothioate (marathon ala
thion), 0.0-dithymer S-methyl lupamoylmethyl phosphoronotioate (nomethoate) dis+eth.

ate), 0.0-trimethyl S-2-(1-methylcarbamoylethylthio)ethyl phosphorothioate (pamidothion vamidothion), 5-(N-ethoxycarbonyl-N-methylcarbamoylmethyl)0.0-trimethylphosphorodithio Eight (mecarbum -ecar)
bam), diethyl 2,2.2-)lichloro-1-hydroxyethylphosphonate (tricumylfone tri
cl+I.

rpl+on), 1,2-nopromo 2,2-nochloroethyl dimethyl phosphate (naled), 2,2-nochlorovinyl methyl phosphate
dichlorovos), 2-chloro-1-(2,4-
dichlorophenyl) vinyl diethyl phosphate (
Chlorofenvinph
os), (Z)-2-chloro-1-(2,4,5-)
(lichlorophenyl) vinyl trimethyl phosphate (
Tetrac Ojk k”/Hoss tetrachlorv
inpl+os), dimethyl (E)-1-methyl-2
-(Methylcarbamoyl)vinyl phosphate (monocrotophos+onocrotophos), 5-6-riaa-2,3-nohydroC1-2-oxobenzoxazol-3-ylmethyl 0,0-tumethylphosphorodithioate (phosal .

ne), 5-2-chloro-1-7thalimidoethyl 0゜0-diethyl phosphonothioate (diaryphos dial
ifos), 0.0-dimethyl O-3,5,6-)lichloro2-
Pyrinol phosphorothioate (chlorpyrifos-methyl ehlorpyrifos-s+ethyl), 0.0
-diethyl O-3,5,6-dolychloro-2-pyridylphosphorothioate (chlorpyrifos chlor
pyrifos).

0-2-diethylamino-6-methylpyrimidine-4-
yl 01O-methyl phosphorothioni 0.0-diethyl 0 2-iso-propyl-6-methylpyrimicin-4-yl phosphorothioate (gui7nonone d
2.3-dihydro-3-oxo-2-phenyl-6-bilignonyl diethyl phosphorothioate (pyridaphenthion), 0.
0-Diethyl O-quinoxalin-2-yl phosphorothioate (quinalphos quinalpl+os), 0
．． 0-diethyl 0-5-phenylisoxazole-3
-ylphosphorothioate (inxathion 1sox
athion), S-2,3-dihydro-5-methoxy-2-oxo-1
,3,4-ticazol-3-ylmethyl0.0-y
Methylphosphorononaoate (methigthione s+et)
hidatl+1on), 2-methoxy-4H-1,3
, 2 people 5-benzonoosa I itl+ ion
).

The organophosphoric esters which form part of the active compound mixture according to the invention are already known. The Pesticide Manual (The Pesticide Manual)
Manual) 7th edition 1983 (TbeBrit
ish Crop Protection Co.
It is already known as an insecticide and has been described in publications such as Unci 1 (Published by Unci 1).

Among the above-mentioned organic phosphoric acid esters, for example, the following agents are preferably used for controlling lepidopteran pests in rice fields, such as the Japanese staghorn beetle and the staghorn beetle. For example, 7
Enthion, quinalfos, sulprofos, 7-entoate, fenitrothion, guy 7-nonone, inoxathion, pyridafenthione, trichlorfon, chlorpyrifos-methyl, marathon, monocrotophos, propafos, EPN, etrimofos and tetrachlorvinphos, etc.

The following agents are preferably used to control common Lepidoptera pests, such as crucian carp, armyworm, leaf beetle, etc. For example, prothiophos, sulprofos, dichlorphos, trichlorfon, cyanophos, pirimiphos-methyl, chlorpyrifos, Tumethoate, Phosaron, Methiguthion, Chlor 7 Envinphos, Acephate, Salithion, Di7 Liphos, Mecarbam, Profenofos, Naildo, 7 Entoate, Fenitrothion, Gui 7 Nonone, Inoxathion, Marathon, EPN.

and cyano7enphos et al.

Alternatively, the following agents are preferably used for controlling horticultural pests, particularly Hemiptera pests, such as aphids such as peach plum, cotton aphid, and apple aphid. etc.

The weight ratios of the active compounds of each group in the active substance combinations can be varied within a relatively wide range. in general,(
1) per part by weight of the active compound of the active compound group of the imino-substituted polycyclic compound of general formula (1), (2) general formula (n)
For example, 0.05 to 10 parts by weight, preferably 0.1 to 5 parts by weight, of an active compound of the active compound group of organic phosphoric acid esters.
Weight parts can be used.

The active substance combination according to the invention exhibits an excellent insecticidal activity, so that the active compound mixture can be used as an insecticide.
It can be used by foliage spraying, underwater or water surface application, soil application, soil mixing treatment, stomach seedling box application, etc.

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

For example, the insecticidal composition of the present invention is particularly effective against lepidopteran insect pests such as paddy field insects such as the Japanese carp, the first lepidopteran insect pests such as crucian carp and armyworm, and hemiptera insect insects such as scale insects and aphids on fruit trees. M-tada's I! II It can be effectively used to control ornamental crops.

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

Coleopteran pests, such as the callosobruchus c.
hiensis), brown weevil (Sitophile)
us zeamais), Lesser brown butterfly (T r
ibol ius castaneum), Japanese lady beetle (Epilachna viginti)
octosaculata), A griotes fuscico1113
, A nomala rufoeupr
ea,), Colorado Potato Beetle (Leptino)
tarsa deeemlineata), 77 pua
Monochamus alt.
ernatus), rice weevil (L 1ssor)
hoptrus oryzophilus), rice weevil (Eehinocinemus square)
us), rice weevil (Oules+a ory
zae), Lyctus br.
uneus): lepidopterous insects, e.g.
ymanLria dispar), Plum beetle (M
alacososa neustria), P. ierisrapae, Sp.
odopLera 1iLura), armyworm (Mam
estra brassicae), Chilo 5uppressalis, Cnapbalocroeis medin
alis), 7 Taobikoya ff (Naranga a
eneseens), Awanomei (Pyraust)
a nubi 1alis), Funamagramai ff (
Ephestia cautella), Adoxophyes orana, Carpocapsa pomonell
a), Cabraya ff (Agrotis fueosa)
), honey ff (Galleria mellon
ella), diamondback moth (P 1utella macu)
lipennis)s Heliothi
s virescens), and the citrus leafminer (P
Hyllocnistis eitrella); P arnara guttata
): Hemiptera insects, such as the leafhopper (N epho
tettix cineticeps), brown planthopper (N 1laparvita Lugens),
Laodelphax 5tria
tellus), red planthopper (Sogatella)
furcifera), Kwafunakai γramun (P
5 eudococcus comstocki), U naspis yanone
nsis), peach aphid (Myzus p.
ersicae), apple aphid (Aphis
pomi), Aphis goss
ypii), Japanese radish aphid (Rhopalo
siphum pseudobrassicas),
S tepbanitis nash
i), green stink bug (Nezara spp, )
, T realeurodes
vaporarioruw), Kiν Fumi (Psyll
a spp, ): on the order Orthoptera, e.g. Gryllotalpa afrieana
), grasshopper (Locusta + *igratoria
sigratoriodes); etc.

The active compound combination 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 a customary formulation of each separately for extemporaneous mixing. Such forms include solutions, emulsions, suspensions, powders, foams,
Pastes, granules, aerosols, active compound infiltration - natural and synthetic products, microcapsules, seed coatings, preparations with combustion devices (e.g. combustion devices (fumigation and fume cartridges, cancer and coils) ), and ULV
(cold mist (cold m1st), warm mist (wara+ m1s1))].

These formulations can be manufactured by known methods. Such a process can be carried out, for example, by combining the active compound with a spreading agent, i.e. a liquid diluent; a liquefied gas diluent; a solid diluent; or a carrier, optionally a surfactant, i.e. an emulsifying agent and/or a dispersing agent and/or This is done by mixing using a foam-forming agent. When using water as a spreading agent, for example,
Organic solvents can also be used as cosolvents.

The body diluent or carrier is generally an aromatic hydrocarbon (e.g. xylene, toluene, alkylnaphthalene, etc.), a chlorinated aromatic or a chlorinated aliphatic hydrocarbon.
(e.g., chlorobenzenes, ethylene chlorides, methylene chloride, etc.), aliphatic hydrocarbons E, e.g., cyclohexane, paraffins (e.g., mineral oil fractions, etc.), alcohols M (e.g., butanol, glycols and their ethers, Ketones (esters, etc.) [(for example acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone etc.), strong polar solvents (for example nomethylforma = ir-dimethyl or sulfoxide etc.) and water may also be mentioned.

Liquefied gas diluents or carriers are gases at normal temperature and pressure, and include, for example, 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,
Montmorillonite or diatomaceous earth''5), soil synthetic mineral (
Examples include highly dispersed silicic acid, alumina, citrate, 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 of organic substances (e.g. , sawdust, coconut shells, corn cobs, tobacco stalks, etc.).

As emulsifiers and/or foaming agents, nonionic and anionic,
On-emulsifiers [e.g., polyoxyethylene fatty acid ester, polyoxyethylene fatty acid alcohol ether (
Examples include alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates, etc.) L fulpmin hydrolysis products.

Examples of powders include genin 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, including inorganic pigments such as iron oxide, titanium oxide and Prussian blue, and organic dyes such as alizarin dyes, azo dyes or metal-7 talocyanine dyes, and furthermore, 'iron,
Just to name a few trace elements like manganese, boron, copper, cobalt, molybdenum, and their salts of zinc.

The formulations may generally contain from 0.1 to 95% by weight, preferably from 0.5 to 90% by weight of said active ingredient.

The active compound combinations according to the invention, in their commercially useful formulations and in the use forms prepared by them, may contain other active compounds, such as insecticides, poison baits, fungicides,
Acaricide, nematocide, fungicide, growth Il! It can also be present as a mixture with conditioners or herbicides.

Here, the above-mentioned insecticides include, for example, carbamate agents, carboxylate agents, chlorinated hydrocarbon agents,
List of insecticidal substances produced by microorganisms.

Furthermore, the active compound 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 concentration for use of the active compound mixture of the present invention can be selected and changed as appropriate, but for example, from o, ooooi to 100% by weight.
The amount is preferably 0.001 to 1% 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 pests against stored plants, 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 should not be limited to this only.

Example 1 SSN of test sample solution for Kobunomei Solvent Nidimethylformamide 3 parts by weight Emulsifier: Polyoxyethylene alkyl phenyl ether 1 part by weight μiν
) 1j-1w Shield h1 In Table 1, 9 parts of the active compound mixture or active compound alone shown in the Tested Drug Field column is mixed with the above amount of solvent containing the above amount of emulsifier, and the mixture is It was diluted with water to the specified concentration.

Test method: Plant height 15cm planted in a vinyl pot with a diameter of approximately 9cm+
- Plant three rice plants, and 10 days after planting, use a spray pump to spray a diluted solution of the active compound in water with a predetermined concentration at 20-1 per bot, and after air-drying the sprayed solution, the diameter is 9 cm. - Cover with a plastic mesh tube with a height of 25c+s, inoculate 10 Copnomei LF 4th instar larvae per pot, and place in a constant temperature room! After 20 days, the number of insects killed was counted and the insecticidal rate was calculated. Note that the test was conducted in duplicate.

The results are shown in Table 1.

Table 1 Test notes for Copnomei 1. No drug damage was observed in all the mixtures and single agent use in the test in Example 1.

2. Compound of general formula (1) used in the present invention: Compound N
o, 11-(2-chloro-5-pyrinolmethyl)-2-
Compound No. 21 (2-chloro-5-pyridylmethyl)
Compound No. 31 (2-chloro-5-thiazolylmethyl)-2-troimino) imidazolidine, Compound No. 41-7 cetyl-3-(2-chloro-5-
Compound No. 53-(2-chloro-5-pyridylmethyl)-2-troimino)thiazolidine, Compound No. 81 (2-chloro-5-pyridylmethyk)
-2- troimino)piperidine, compound, No. 71
-(2-chloro-5-bilinormethyl)-2-(cyanoimino)imidazolidine, 3. Compounds used in the present invention: [A]: Inoxathion [B]: Pyridafenthione [C]: Tetrachlorvinphos [Dl : Sulprophos Example 2 Test against diamondback moth Test method: A non-heading cabbage violet with a diameter of about 15 cm planted in a pot of a horse mackerel with a diameter of 9 cm was injected with the active compound mixture or activity shown in the column of test drugs in Table 2 below. Besides using the compound alone,
A water dilution of a given concentration of the active compound prepared as in Example 1 was applied using a spray gun to 20 ml/bot.
After the sprayed chemical solution was air-dried, each bot was inoculated with 910 4th instar larvae of organophosphate-resistant two-spotted larvae and placed in a constant temperature room. ! 2
The insect kill rate was calculated by counting the mortality in the caliber. The test was conducted using a two-part system.

The results are shown in Table 2.

Table 2 Test notes for crucian carp) 1. No chemical damage was observed in all the mixtures and single agent use in the test in Example 2.

2. Compound No. 1 of general formula (1) used in the present invention
, No, 2, No, 3, No, 4, No, 5, N
o, 6 and No. 7 indicate the same compounds as in Example 1.

3. Compounds used in the present invention: [E]: Prothiophos 1F1: Virimiphos-methyl 1G": Chlorpyrifos [H] niacefneet Example 3 Test against cotton aphids Test method: Planted in a pot with a diameter of 9c and a height of about 15cm+ Approximately 100 cotton aphids reared on eggplant seedlings were inoculated per seedling, and one day after inoculation, an active compound mixture or an active compound alone as shown in the test chemical column in Table 3 was used. A spray gun was used to spray a diluted solution of the activated compound in water at a predetermined concentration, prepared as in Example 1, at 20 g/bottle.
After spraying, the plants were left in a greenhouse at 28°C, and 2 days after spraying, the growth was counted and the mortality rate was calculated.

The results are shown in Table 3.

Table 3 Tests against cotton aphids (Notes) 1. No chemical damage was observed in all the mixtures and single agents used in the test in Example 3.

2. Compound No. 1 of general formula (1) used in the present invention,
No, 2, No, 3, No, 4, No, 5, N
o, 6 and No. 7 indicate the same compounds as in Example 1.

3. Compounds used in the present invention: [■] Nidisulfoton [Jl: Bamidothione Example (Irrigation agent) 20 parts of active compound of formula (1), 20 parts of active compound prothiophos of formula (n), powdered diatomaceous earth and 55 parts of a mixture with powdered clay (1:5), 2 parts of sodium alkylbenzenesulfonate, and 3 parts of sodium alkylnaphthalenesulfonate formalin condensate are ground and mixed to prepare a wettable powder.

Examples (Powder) 1 part of the active compound of the formula (1), 2 parts of the active compound pyguaninethione of the formula (II), and 97 parts of powdered clay are ground and mixed to prepare a powder.

Example (Granules) 96 parts of clay minerals having a particle size distribution of 0.2 to 2 rings were placed in a rotary mixer and dissolved in an organic solvent under rotation.
) and 2 parts of active compound disulfoton of formula (II) were sprayed and t6s! After soaking in 9 4
Dry at 0 to 50°C to form granules.

1 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) General formula ▲ Numerical formula, chemical formula, table, etc. ▼ (II) In the formula, X^1 represents an oxygen atom or a sulfur atom, and X^2 represents an oxygen atom, a sulfur atom, or a Represents a direct bond between a phosphorus atom and R^3, R^1 represents a lower alkyl group, R^2 represents a lower alkoxy group, lower alkylthio group, lower alkylcarbonylamide group, or phenyl group, R^3 represents each represents a substituted or unsubstituted lower alkyl group, lower alkenyl group, phenyl group or heteroaryl group,
or R^2 and R^3 together represent the phosphorus atom and X in the formula
An insecticidal composition for agriculture and horticulture, characterized in that it contains an active substance combination consisting of at least one compound selected from organophosphoric acid esters represented by the following, which together with ^2 represent a phosphorine ring.