JPH0344304A - Insecticidal and bactericidal composition for agricultural and horticultural use - Google Patents

Abstract

PURPOSE:To obtain the subject composition exhibiting synergistic insecticidal and bactericidal activity at a low concentration compared with the separate use of each component and exhibiting excellent quick activity and residual activity by combining an alpha-unsaturated amine with a known specific bactericidal compound. CONSTITUTION:The objective composition is produced by combining (A) 1 pt.wt. of a compound of formula (one of X<1> and X<2> is electron-attracting group and the other is H or electron-attracting group; R<1> is group bonded through N; R<2> is H or group bonded through C, N or O; n is 0-2; A is heterocyclic group or cyclic hydrocarbon group), e.g. 1-[N-(6-chloro-3-pyridylmethyl)-N- methyl]amino-1-methylamino-2-nitroethylene and (B) 0.5-50 pts.wt. of a compound selected from pherimzon, fusaride, probenazole, isoprothiolane, kasugamycin hydrochloride, edifenphos, isoprobenphos, tricyclazole, validamycin A, flutranyl, mepronyl and pencyclone.

Description

Detailed Description of the Invention (a) Industrial Application Field The present invention provides an excellent insecticidal and bactericidal action consisting of a combination of α-unsaturated amines of the formula [1] below or a salt thereof and a known bactericide. This invention relates to a novel agricultural and horticultural insecticide and fungicide.

(B) Conventional Technology Various pesticides have been developed as agricultural and horticultural insecticides, such as organic phosphorus, carbamate, and pyrethroid pesticides, and have been used as single agents or mixtures. However, conventional insecticides lack a balance in terms of insecticidal spectrum, insecticidal activity at each stage of insect pest development, immediate effect, residual effect, systemic transfer, etc., and even though they have excellent insecticidal effects, they are toxic to fish and Alternatively, due to safety issues against useful insects and natural enemies, and chemical damage to crops, the situations and number of uses are limited, and as a result, it cannot be said that a satisfactory insecticidal effect is achieved. In particular, pests that have recently become less sensitive to conventional pesticides, such as leafhoppers and planthoppers that are resistant to organic phosphorus agents and carbamates in Japan's rice fields, have emerged, and the establishment of control technologies for these pests. is strongly requested.

A similar situation is observed in the field of fungicides, especially in the field of fungicides.
Recently, the susceptibility of rice blast hemorrhoid pathogens and rice sheath blight pathogens of paddy rice to conventional fungicides has decreased, making it difficult to control them, and there is a strong demand for the establishment of control techniques for these pathogens.

Furthermore, in recent years, there has been a strong demand for so-called cost reduction in the control of these pests, and it is necessary to achieve high control effects with fewer treatments and fewer doses of chemicals, and there is a demand for the development of chemicals that can meet these demands. .

In addition, in recent years, mechanical transplantation of young seedlings has become widespread as one of the paddy rice cultivation techniques in Japan, and this has led to the use of not only conventional chemical treatment directly to paddy fields but also the transfer of chemicals.
There is a strong desire for the development of an excellent drug that can control pests and diseases through seedling nursery box treatment or side-row application at the time of transplantation, that is, a drug that exhibits medicinal efficacy and is free from phytotoxicity.

Furthermore, it is already known that the following fungicides have control activity against rice blast or rice sheath blight. for example,
(Z)-2'-methylacetophenone-4,6-dimethylpyrimidin-2-ylhydrazone (ferimcin),
4,5.6.7-Tetrachlorophthalide (Fusalide)
, 3-alkyloxy-1,2-benzisothiazole-1゜1-dioxide (probenazole), diisopropyl-1,3-dithiolane-2-ylidene-malonate (isobrothiolane), kasugamycin hydrochloride (kasugamycin), 〇 -Ethyl-S,S-diphenyldithiophosphate (nidifenphos), 01O-diisopropyl-8-benzylthiophosphate (ibrobenphos)
, 5-methyl-1゜2.4-triazolo[3,4-b]
Benzothiazole (tridiclazole) etc. are used as a control agent for rice blast, etc., and for example, validamycin A (
validamycin), α, α, α-trifluoro-3-isopropoxy-0-toluanilide (flutolanil), 5
-Methyl-1,2-methylbenzanilide (Mepronil), L-(4-chlorobenzyl)-1-cyclopentyl-3-phenylurea (Benziclon), etc. are used as control agents for rice sheath blight, etc. in the Pesticide Manual ( The P
Esticide Manual 8th edition 1987 The
Br1tish Crop Protection C
published by onci1), etc.

(c) Problems to be Solved by the Invention However, the effects of the above-mentioned known insecticidal compounds and bactericidal compounds, when used alone, only exhibit either a bactericidal effect or a bactericidal effect; It is not possible to simultaneously prevent damage caused by On the other hand, the present inventors discovered that unsaturated amines of the following formula [l] or their salts are effective as insecticides, and filed a patent application (Japanese Patent Application No. 192383-1983). While considering more effective use of these unsaturated amines, we researched their combination with the above-mentioned known fungicidal compounds, and found that a cooperative insecticidal and fungicidal effect that could not be obtained by using either alone was obtained. ,
It was also found that the toxicity was satisfactory.

(d) Means for Solving the Problems According to the present invention, (1) Formula [lco[wherein one of x' and x'' is an electron-withdrawing group and the other is a hydrogen atom or an electron-withdrawing group, R1 is a group via a nitrogen atom,
1 represents a hydrogen atom or a group via a carbon, nitrogen or oxygen atom, n represents 0.1 or 2, and A represents a heterocyclic group or a cyclic hydrocarbon group. However, when R1 is β-N-pyrrolidinoethylamino and R'' is a hydrogen atom, A represents a group represented by a formula atom).
- at least one unsaturated amine or a salt thereof, (2) (Z)-2'-methylacetophenone-4゜6-
Dimethylpyrimidin-2-ylhydrazone (Ferimsin), 4.5.6.7-Tetrachlorphthalide (Fusalide)
, 3-alkyloxy-1,2-benziisothiazole-
1,t-dioxide (probenazole), diisopropyl-! , 3-dithiolane-2-ylidene-malonate (
isobrothiolane), kasugamycin hydrochloride (kasugamycin), 0-ethyl-6,S-diphenyldithiophosphate (nidifenphos), 0.0-diisopropyl-8-benzylthiophosphate (isopropenphos), 5-methyl-1 , 2,4-triazolo[3,4-d]benzothiazole (tridiclazole), validamycin A (validamycin), α, α, α-triple oro 5
-Methyl-1,0-tolu anilide (flutolanil),
At least one selected from the group consisting of 5-methyl-1,2-methylbenzanilide (mepronyl), 1,4-chlorobenzyl)-1-cyclopentyl-3-phenylurea (benziclone), etc. An agricultural and horticultural insecticidal and fungicidal composition characterized by containing a seed compound.

The insecticidal and/or bactericidal activity of the insecticidal and/or bactericidal composition according to the present invention, in which the α-unsaturated amine of formula [1] or its salt is blended with the above-mentioned known fungicide, is determined by the sum of the effects of each individual active compound. It is clearly large in size, exhibits excellent synergistic action, and has excellent fast-acting and residual effects.

In particular, the insecticidal and fungicidal composition of the present invention can be applied for the purpose of controlling pests (diseases and insect pests) of agricultural crops, such as Hemipteran pests such as leafhoppers and planthoppers, which are important pests of paddy rice. Cooperative insecticidal action against rice blast fungi and rice sheath blight fungi, which are important disease pathogens of paddy rice, at lower concentrations than when using only a single active compound. It exhibits bactericidal activity and exhibits both immediate and persistent efficacy.

(Left space below) In the above formula [1], one of Xl and x8 represents an electron-withdrawing group, and the other represents a hydrogen atom or an electron-withdrawing group, and the electron-withdrawing group represented by xl and xt is, for example, cyano. Nitro, alkoxycarbonyl (e.g., C+-*alkoxy-carbonyl such as methoxycarbonyl, ethoxycarbonyl, etc.), hydroxycarbonyl, C11゜aryluoquinecarbonyl (e.g., phenoxycarbonyl, etc.), heterocyclic oxycarbonyl (1 The following are used, such as pyridyloxycarbonyl, thienyloxycarbonyl, etc.), C1□alkylsulfonyl which may be substituted with halogen, etc. (for example, methylsulfonyl, trifluoromethylsulfonyl,
ethylsulfonyl, etc.), aminosulfonyl, di-C1-
4-alkoxyphosphoryl (e.g. jetoxyphosphoryl etc.), C optionally substituted with halogen etc.
1-4 acyl (e.g. acetyl, trichloroacetyl, trifluoroacetyl, etc.), carbamoyl + Cl-4
Alkylsulfonylthiocarbamoyl (eg, methylsulfonylthiocarbamoyl, etc.) and the like are used. XI
, Xl may represent a halogen atom such as fluorine, chlorine, bromine, or iodine, and a preferable example of a group in which Xl and X8 are bonded and adjacent to each other is, for example, 0tNCH=.

A group represented by the above formula [l], where R1 is a nitrogen atom, or the like is used. Here, R@ is a hydrogen atom, alkyl (eg methyl, ethyl).

n-propyl, i-propyl, n-butyl, i-butyl.

Ct-*alkyl such as n-hexyl), C*-+. Aryl (e.g. phenyl, etc.), aralkyl (e.g. 071 aralkyl such as benzyl), heterocyclic group (e.g. the following, specifically pyridyl etc.), CI-*acyl (e.g. formyl, acetyl, propionyl etc.) C
, -1°aryl-carbonyl (eg, benzoyl, etc.), alkoxycarbonyl (eg, CI-4 alkoxycarbonyl, such as methquin carbonyl, ethoxycarbonyl, etc.), Cs-+. Aryl-oxycarbonyl (for example, phenoxycarbonyl, etc.), heterocyclic oxycarbonyl (the following are used as the heterocyclic group, for example, furyloxycarbonyl, etc.), Ct-,. Arylsulfonyl (e.g. phenylsulfonyl), alkylsulfonyl (e.g. methylsulfonyl etc.)
4 alkylsulfonyl).

Dialkoxyphosphoryl (e.g. di-Cl-4 alkoxyphosphoryl such as jetoxyphosphoryl).

Alkoxy (e.g. methoxy, ethoxy, etc. 01-4)
alkoxy), hydroxy, amino, dialkylamino (e.g. dimethylamino, diethylamino, etc.)
1-4 alkylamino), acylamino (e.g. Cl-4 acylamino such as formylamino, acetylamino, propionylamino, etc.), alkoxycarbonylamino (e.g. Cl-4 alkoxy-carbonylamino such as metquine carbonylamino), alkylsulfonylamino ( For example, Cl-4furkylsulfonylamino such as methylsulfonylamino), dialkoxyphosphorylamino (such as di-C3 such as jetoxyphosphorylamino)
, alkoxyphosphorylamino), Ct-1 aralkyloxy (e.g. benzyloxy, etc.), alkoxycarbonylalkyl (e.g. CI-4 alkoxy-carbonyl-Ct-a alkyl such as methoxycarbonylmethyl), etc., R7 is a hydrogen atom, 1 ~3 substituents (e.g. Ct-a alkoxy such as hydroxy, methoxy,
Halogens such as fluorine, diCl-4 such as dimethylamino
Alkylamino 01-4 alkylthio such as i-propylthio and n-propylthio.

Cl-3 such as acetylamino; CI- such as acylamino, methylsulfonylamino; alkylsulfonylamino,
alkyl (e.g., 01-, alkyl such as methyl, ethyl), cycloalkyl (such as 01-, alkyl such as methyl, ethyl), cycloalkyl (such as pyridyl or thiazolyl, which may be substituted with halogen, etc.); For example, C5-. ) etc. Furthermore, R@ and R? may represent, for example, a 5- or 6-membered cyclic amino group when bonded to an adjacent nitrogen atom.

Preferred examples of the group represented by R1 via a nitrogen atom include (for example, alkyl, aryl, aralkyl, heterocyclic group, acyl, alkoxycarbonyl, aryloxycarbonyl, heterocyclic oxycarbonyl as described above for R@, R?) , arylsulfonyl, alkylsulfonyl, dialkoxyphosphoryl, cycloalkyl,
Alkenyl, cycloalkenyl, alkynyl, and other optionally substituted aminos (especially di-substituted aminos such as di-c+-e alkylamino, N-C+-s alkyl-N-formylamino, mono-C1-@alkylamino, etc.) substituted amino, unsubstituted amino), (for example, alkylacyl, alkoxycarbonyl, alkylsulfonyl, dialkoxyphosphoryl, etc. as described in R3 below)
hydrazino, which may be substituted (for example, alkyl, aralkyl, etc. as described in R3 below), hydroxyamino, which may be substituted with potassium, etc. Specifically, the formula
-N<R: A group represented by (R' and R7 have the same meanings as above) is often used as R1.

R8 represents a hydrogen atom or a group via a carbon, nitrogen or oxygen atom. Examples of the group represented by R1 via a carbon atom include Cl-5 acyl (e.g., formyl, acetyl, propionyl, etc.), alkyl (e.g., methyl,
ethyl, n-propyl, i-propyl, n-butyl, i
-butyl, Cl-4 alkyl such as 1ilac-butyl)
, alkenyl (e.g. CI-4 alkenyl such as vinyl, allyl, etc.), cycloalkyl (e.g. C1-, cycloalkyl such as cyclopentyl, cyclohexyl, etc.), C
S-t. Aryl (for example, phenyl, etc.), aralkyl (for example, C10 such as benzyl, aralkyl, etc.), heterocyclic group having a bond on a carbon atom (for example, the following, specifically 3- or 4-pyridyl group, etc.) These groups contain 1 to 3 substituents (for example, 01-4 alkylthio such as methylthio and ethylthio, CI-4 alkoxy such as methoxy and ethoxy, mono- or di-C+- such as methylamino and dimethylamino). +C+-*alkoxy-carbonyl, methylsulfonyl, such as alkylamino, methoxycarbonyl, ethoxycarbonyl.

Cl-4 alkylsulfonyl such as ethylsulfonyl.

Halogens such as fluorine, chlorine, bromine, and iodine, C1,4 acyl such as acetyl, benzoyl, phenylsulfonyl,
pyridyl, etc.). As the group represented by R1 via a nitrogen atom, for example, those mentioned above for R1 can be used. The oxygen atom represented by R'' is F
Examples of the group include alkoxy (for example, C1-4 alkoxy such as methoxy and ethoxy), cycloalkoxy (for example, C1-6 cycloalkoxy such as cyclohexyloxy), alkenyloxy (for example, 01- and alkenyloxy such as vinyloxy and allyloxy). ),
Cycloalkenyloxy (for example, Cs-+s cycloalkenyloxy such as cyclohexenyloxy), alkynyloxy (for example, ethynyloxy, etc.), C6□0 aryloxy (for example, phenoxy, etc.), heterocyclic oxy (heterocyclic groups include the following) For example, thienyloxy), hydroxyl group, etc. are used, and these are 1
It may have ~3 substituents (for example, halogens such as fluorine, chlorine, and bromine, phenyl, etc.).

Preferred examples of R'' are groups via carbon, nitrogen or oxygen atoms, such as formyl, (e.g. the above-mentioned C+-a alkylthio, Cl-4 alkoxy, mono- or di-C9-4 alkylamino+Cl- C5 which may be substituted with potassium such as 4 alkoxy-carbonyl + Cl-4 alkylsulfonyl, halogen such as fluorine and chlorine, acetyl, benzoyl, phenylsulfonyl, pyridyl, etc.
, 4 alkyl (particularly C1-4 alkyl such as methyl, ethyl, etc.), optionally substituted amino (for example, the above R1
(such as optionally substituted amino as mentioned above), (for example, the above-mentioned 01-4 alkyl).

Cj-m cycloalkyl, Ct-4 alkenyl + Cj-
#Cycloalkenyl, C1-a alkynyl + Cl-10
Aryl,? J [a hydroxyl group which may be substituted with potassium such as a cyclic group (particularly 01-4 alkoxy such as methoxy), etc.

n represents 0.1 or 2. Therefore, −C1 in formula (1)
H*, 1- is a single bond, CH! , CHtCH
*-Frequently used.

A is a heterocyclic group (such as the following, in particular the following substituents (i), (iv), (vi), (x vi), (x
Heterocyclic groups which may be substituted with 1 to 3 members such as
-Birinol, 6-methyl-3-pyridyl, 6-buam-3-pyridyl, 6-fluoro-3-pyridyl, 2-chloro-5-thiazolyl, 4-pyridyl, 2-pyrazinyl,
2-thiazolyl, 4-thiazolyl, 3-quinolyl, etc.), and A may further be substituted with a cyclic hydrocarbon group (for example, the following, particularly one or two of the following substituents (xvi)) A cyclic hydrocarbon group is used, specifically cyclopropyl, cyclohexyl, phenyl, p-chlorophenyl, etc.). Preferred examples of the heterocyclic group represented by A include 3-pyridyl, 4-pyridyl, 6-pyridyl, etc.
Chloro-3-pyridyl, 6-bromo-3-pyridyl.

These include optionally substituted pyridyl or thiazolyl such as 6-fluoro-3-pyridyl and 2-chloro-5-thiazolyl. Preferred examples of the cyclic hydrocarbon group represented by A include halogenophenyl such as p-chlorophenyl.

Alkyl, cycloalkyl, alkenyl in the above definitions of x', x'', R', R2, Ro, R?, A.

As the cycloalkenyl, alkynyl, aryl, aralkyl, heterocyclic group, and cyclic hydrocarbon group, for example, the following can be used, and these groups also include l to 5 ([
Ji may have substituents such as the following (i) to (Lii).

The alkyl preferably has 1 to 20 carbon atoms,
Charcoal number 1 and number 1 to 8 are more preferable. The alkyl may be linear or branched. Specific examples of the alkyl include methyl, ethyl,
Propyl, isopropyl, butyl, isobutyl, 5e
c-butyl, tert-butyl, pentyl 5-hexyl, heptyl, octyl, nonyl, 2-ethylhexyl,
Decile, undecile. Dodecyl.

Tridecyl, tetradecyl, pentadecyl, hexadecyl, octadecyl, nonadecyl, eicosyl, etc. are used.

The cycloalkyl preferably has 3 to 6 carbon atoms, and examples thereof include cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl.

The alkenyl preferably has 2 to 6 carbon atoms.

Specific examples of the alkenyl include vinyl, allyl, isopropenyl, methallyl, (,
[-dimethylallyl, 2-butenyl, 3-butenyl, 2
-pentenyl, 4-pentenyl, 5-hexenyl, etc. are used.

The cycloalkenyl preferably has 3 to 6 carbon atoms, and specific examples thereof include 1-cyclopropenyl, 2-cyclopropenyl, l-cyclobutenyl,
2-cyclobutenyl, 1-cyclopentenyl, 2-cyclopentenyl, 3-cyclopentenyl, l-cyclohexenyl, 2-cyclohexenyl, 3-cyclohexenyl, 1.3-7 clohexadien-1-yl, 1.4- Cyclohexadien-1-yl, 1,3-cyclo, lobentadien-l-yl, 2,4-cyclopentadien-I-
etc. are used.

As alkynyl, those having 2 to 6 carbon atoms are preferable,
Specific examples include ethynyl, propargyl, 2-butyn-1-yl, 3-butyn-1-yl, 3
-butyn-2-yl, 1-pentyn-3-yl, 3-pentyn-1-yl, 4-pentyn-2-yl, 3-hexyn-1-yl, etc. are used.

Examples of aryl include phenyl and naphthyl.

Examples of aralkyl include benzyl, phenylethyl, naphthylmethyl, and the like.

Examples of the heterocyclic group include a 5- to 8-membered ring containing 1 to 5 heteroatoms such as an oxygen atom, a sulfur atom, and a nitrogen atom, or a condensed ring thereof. 3-thienyl, 2- or 3-furyl9
2- or 3-pyrrolyl, 2-. 3- or 4-pyridyl, 2-. 4- or 5-oxasilyl, 2-. 4- or 5-thiazolyl, 3-. 4- or 5-pyrazolyl, 2-. 4- or 5-imidazolyl, 3-. 4- or 5-isoxacylyl, 3-. 4- or 5-isothiazolyl, 3- or 5-(1,2,4-oxadiazolyl), 1.3.4-oxadiazolyl, 3- or 5-(1,2,4-thiadiazolyl), 1.3.4 -thiadiazolyl, 4- or 5-(1,2,3-thiadiazolyl), 1.2.5-thiadiazolyl, 1.2.3-
Triazolyl! , 2.4-)riazolyl, II(- or 2H-tetrazolyl, N-oxido-2-03- or 4-pyridyl, 2-.4- or 5-pyrimidinyl, N-oxyto-2-14- or 5 -pyriminonyl,
3- or 4-pyridazinyl, pyrazinyl, N-oxide-3- or 4-pyridazinyl, benzofuryl, benzothiazolyl, benzoxacylyl, triazinyl, oxotriazinyl, tetraclo[1,5-b]pyridazinyl, triazolo[45-b ] Pyridazinyl, oxoimidazinyl, dioxotrianonyl, pyrrolidinyl, piperidinylpyranyl, thiopyranyl,! , 4-oxazinyl, morpholinyl, ! , 4-thiazinyl, 1,3-thiazinyl.

Piperazinyl, benzimidazolyl, quinolyl, isoquinolyl, cinnolinyl, phthalazinyl, quinazolinyl,
Quinoxalinyl, intridinyl, quinalinyl! , 8
- Naphthyridinyl, purinyl, pteridinyl, dibenzofuranyl, carbazolyl, acridinyl, phenanthridinyl, fenadinyl, phenothiazinyl, phenoxazinyl, etc. are used.

Examples of the cyclic hydrocarbon group include C3 such as cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl.
c such as -6 cycloalkyl, l-cyclopropenyl, 2-cyclobutenyl, l-cyclohexenyl, 2-cyclohexenyl, 1,3-cyclohexadien-1-yl,
-8 cycloalkenyl, phenyl, naphthyl, etc. 06□
. Aryl etc. are used.

(i) C+--alkyl, such as methyl, ethyl.

Propyl, isopropyl, butyl, isobutyl, sec
-butyl, tert-butyl, etc. are used.

(ii) Cs-s cycloalkyl such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl and the like is used.

(iii) Co-+. Aryls such as phenyl, naphthyl, etc. are used.

(iv) C+-*alkoxy, such as methoxy, ethoxy, propoxy, isopropoxy, butoxy, ter
T-butoxy and the like are used.

(v) Cs-s cycloalkyloxy such as cyclopropyloxy, cyclopentyloxy, cyclohexadiene, etc. may be used.

(vi) Ce-+o aryloxy, such as fenoquine, naphthylthione, etc., are used.

(vii) Ct-+taralkyloxy, such as benzyloxy, 2-phenethyloxy, 1-phenethyloxy, etc., are used.

(vi) C+-*alkylthio, such as methylthio.

Ethylthio, propylthio, butylthio, etc. are used.

(ix) Cz-s cycloalkylthio, such as cyclopropylthio, cyclopentylthio, cyclohexylthio, etc. are used.

(x) C·-1o arylthio, such as phenylthio, naphthylthio, etc., are used.

(xi) C7-+□aralkylthio, such as benzylthio, 2-phenethylthio,! -Phenethylthio etc. are used.

(xi) MonoC1-, alkylamino, such as methylamino, ethylamino, propylamino, isopropylamino, butylamino, isobutylamino.

Tert-butylamino or the like may be used.

()(iii) DiC1-4 alkylamino, such as dimethylamino, diethylamino, dipropylamino.

Dibutylamino, N-methyl-N-ditylamino.

N-methyl-N-propylamino, N-methyl-N-butylamino, etc. are used.

(xiv) C3-s cycloalkylamino such as cyclopropylamino, cyclopentylamino, cyclohexylamino and the like is used.

(xv) C·-10 arylamino such as anilino is used.

(xvi) Ct-+taralkyl amino, such as benzylamino, 2-phenethylamino, l-phenethylamino, etc., are used.

(xvi) Halogens such as fluorine, chlorine, bromine.

Iodine is used.

(xvi) C+-*alkoxycarbonyl, such as methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, isopropoxycarbonyl, butoxycarbonyl, tert-butoxycarbonyl, isobutoxycarbonyl, and the like are used.

(xix)Co□. Aryloxycarbonyl such as phenoxycarbonyl may be used.

(XX) C3-11 cycloalkyloxycarbonyl,
For example, cyclopropyloxycarbonyl, cyclopentyloxycarbonyl, cyclohexyloxycarbonyl, etc. are used.

(xxi) C6-+taralkyloxycarbonyl, such as benzyloxycarbonyl, 1-phenethyloxycarbonyl, 2-phenethyloxycarbonyl, and the like.

(xxi) C+-s alkanoyl, such as formyl,
'Acetyl, propionyl, butyryl, pivaloyl, etc. are used.

(x x 1ii) C+-ts alkanoyloxy, such as formyloxy, acetoxy, butyryloxy,
Pivaloyloxy, pentanoyloxy, hexanoyloxy, heptanoyloxy, octanoyloxy, nonanoyloxy, decanoyloxy, undecanoyloxy, dodecanoyloxy, tridecanoyloxy, tetrazokayloxy, pentadecanoyloxy, etc. used.

(xxiv) carbamoyl which may have a substituent,
For example, carbamoyl, N-methylcarbamoyl, N
, N-dimethylcarbamoyl, N-ethylcarbamoyl, N,N-diethylcarbamoyl, N-phenylcarbamoyl, pyrrolidinocarbamoyl, piperidinocarbamoyl, piperazinocarbamoyl, morpholinocarbamoyl, N-pennolcarbamoyl, and the like.

(XXV) Carbamoyloxy bearing a substituent, such as N-methylcarbamoyloxy, N.

N-dimethylcarbamoyloxy, N-ethylcarbamoyloxy, N-benzylcarbamoyloxy, N,N
-dibenzylcarbamoyloxy, N-phenylcarbamoyloxy, etc. are used.

(x x vi) CI-4 alkanoylamino, such as formylamino, acetamide, propionamide.

Butyrylamide and the like are used.

(X Xvii) Ca-+oarylcarbonylamino, such as benzamide, is used.

(x x vi) C+-4 alkoxycarbonylamino, such as methoxycarbonylamino, ethoxycarbonylamino, butoxycarbonylamino, tert-
Butoxycarbonylamino and the like are used.

(X
-methoxybenzyloxycarbonylamino.

4-nitrobenzyloxycarbonylamino, 4-chlorobenzyloxycarbonylamino, etc. are used.

(XXX) Substituted sulfonylamino, such as methanesulfonylamino, ethanesulfonylamino, butanesulfonylamino, benzenesulfonylamino, toluenesulfonylamino, naphthalenesulfonylamino, trifluoromethanesulfonylamino, 2-chloroethanesulfonylamino, 2,2,2-trifluor Lomethanesulfonylamino and the like are used.

(xxxi) A heterocyclic group, a cyclic group containing 1 to 5 nitrogen atoms, oxygen atoms, or sulfur atoms, such as pyrrolidinyl, 2- or 3-pyrrolyl, 3-. 4- or 5-pyrazolyl, 2-. 4- or 5-imidazolyl, 2- or 3-furyl, 2- or 3-thienyl, 2-. 4-
or 5-oxasilyl, 3,4- or 5-isoxasilyl, 3-. 4- or 5-isothiazolyl, 2-
．． 4- or 5-thiazolyl 1-piperidinyl, 2-. 3
- or 4-pyridyl, piperazinyl, pyrimidinyl,
Pyranil.

Tetrahydropyranyl, tetrahydrofuryl, indolyl, quinolyl, 1.3.4-oxadiazolyl.

Cheno[2,3-d]pyrazolyl! , 2.3-thiadiazolyl, l , 3.4-thiadiazolyl, 1,2.3
-triazolyl, 1,2.4-)riazolyl, 1.3.
4-triazolyl, tetrazolyl, 4,5-dihydro-
1,3-dioxoryl, tetrasilo[1,5-b]pyridazinyl, benzothiazolyl, benzoxacylyl.

Benzimidazolyl, benzothienyl, etc. are used.

(xxxii) heterocyclic thio, heterocyclic oxy, heterocyclic amino or heterocyclic carbonylamino, the above heterocyclic group (x
A group in which xxi) is bonded to a sulfur atom, an oxygen atom, a nitrogen atom or a carbonylamino group, respectively, is used.

(x x x 1ii) DiC1,4-alkylphosphinothioyl amino, such as dimethylphosphinothioyl amino, diethylphosphinothioyl amino, etc., is used.

(xxxiv) alkoxyimino, such as methoxyimino, ethoxyimino, 2-fluoroethoxyimino,
Carboxymethoxyimino, ■-carboxy1-methylethoxyimino, 2.2 2-trichloroethyloxycarbonylmethoxyimino.

,2,2,2-)lichloroethyloxycarbonyl)-
1-methylethoxyimino, (2-aminothiazole-
4-yl)methoxyimino, (IH-imidazole-4
-yl)methoxyimino, etc. are used.

(x x

(x x x vi)Cs-+. Arylsulfonyloxy such as benzenesulfonyloquine and toluenesulfonyloxy is used.

(xxxvii) Geet C. Arylphosphinothioyl amino, such as diphenylphosphinothioyl amino, is used.

(xxxvi) Thiocarbamoylthio which may have a substituent, such as thiocarbamoylthio, N-methylthiocarbamoylthio, N,N-dimethylthiocarbamoylthio, N-ethylthiocarbamoylthio, N-benzylthiocarbamoylthio, N.

N-dibenzylthiocarbamoylthio, N-phenylthiocarbamoylthio, etc. are used.

(xxxix) Silyloxy such as trimethylsilyloxy, t-butyldimethylsilyloxy, -butyldiphenylsilyloxy, dimethylphenylsilyloxy, etc. is used.

(xL) Silyl such as trimethylsilyl, 1-butyldimethylsilyl, t-butyldiphenylsilyl, dimethylphenylsilyl and the like is used.

(xLi)Ct□Alkylsulfinyl, such as methylsulfinyl, ethylsulfinyl, propylsulfinyl, butylsulfinyl, etc., are used.

(XLii) Ca-+. Arylsulfinyl such as phenylsulfinyl, naphthylsulfinyl, etc. are used.

(x Li1i)C+-a alkylsulfonyl such as methanesulfonyl, ethanesulfonyl, butanesulfonyl, etc. are used.

(xLiv)Go-+. Arylsulfonyl such as benzenesulfonyl, toluenesulfonyl and the like is used.

(XLV)CI-4 Alkoxycarbonyloxy, such as methoxycarbonyloxy, ethoxycarbonyloxy, tert-butoxycarbonyloxy, etc., is used.

(xLvi) C, ~4 haloalkyl, such as trifluoromethyl, 1,1,2,2-tetrafluoroethyl.

Difluoromethyl, monofluoromethyl, trichloromethyl, dichloromethyl, monochloromethyl, etc. are used.

(x Lvii) C,-, haloalkyloxy, C,-
, haOalkylthio+Cl-4 haloalkylsulfinyl or C1-4 haloalkylsulfonyl, for example, the above C1-4 haloalkyl (xlvi) is each an oxygen atom.

A group bonded to a sulfur atom, a sulfinyl group, or a sulfonyl group is used.

(xLvi) cyano group, nitro group, hydroxyl group, carboxyl group, sulfonic acid group and phosphonic acid group.

(xLix)Ct-*alkyloxysulfonyl, such as methoxysulfonylethoxysulfonyl, butkinsulfonyl, etc., are used.

(L) c s-,. Aryloxysulfonyl such as phenoxysulfonyl, tolyloxysulfonyl and the like is used.

(Li)Cy-, aralkyloxysulfonyl such as benzyloxysulfonyl, 2-phenethyloxysulfonyl, l-phenethyloxysulfonyl, etc. are used.

(Lii) di-CI-4 alkyloxyphosphoryl, such as dimethoxyphosphoryl, jetoxyphosphoryl,
Dibutoxyphosphoryl and the like are used.

Preferred examples of the α-unsaturated amines or salts thereof represented by the formula [1] are, for example, those represented by the formula [wherein R1 is a mono〇+-*alkylamino group, N-
c I-@alkyl-N-formylamino group or amino group, Rla is CI-, an alkyl group or C1-.

an alkoxy group, Aa is a chloropyridyl group, α-unsaturated amines or salts thereof, represented by the formula [wherein R''6 is mono-010, an alkylamino group, or N -c + -a alkyl-N α-unsaturated amines or salts thereof represented by formula C, where RIc represents a di-cl-6 alkylamino group, R
tb is a hydrogen atom, formyl or c, -4 alkyl group, A is pyridyl or chloropyridyl group] α-unsaturated amines or salts thereof, represented by the formula [symbols in the formula have the same meanings as above] α−
These include unsaturated amines or their salts.

Upper i2 [1a], [lb], [1c] middle, Rla'Hz
U R” mono-01-. The alkylamino group is, for example, monomethylamino, monoethylamino,
Mono-n-propylamino, mono-1-propylamino, mono-n-butylamino, mono-1-butylamino,
Mono-n-hexylamino, etc., preferably mono 〇, such as monomethylamino, monoethylamino, etc.
-4 alkylamino and the like. The N G+-e alkyl-N-formylamino group represented by Rla and R"b is, for example, N-methyl-N-formylamino, N-ethyl-N-formylamino, N-n-propyl-N-formylamino , N-1-propyl-N-formylamino,
N-butyl-N-formylamino, N-n-hexyl-N-formylamino, etc., preferably N- such as N-methyl-N-formylamino, N-ethyl-N-formylamino, etc. C+-4 alkyl-N-formylamino and the like. The di-Ct-S alkylamino group represented by RIC is, for example, dimethylamine, N-ethyl-N-methylamino, diethylamino, di-n-propylamino, di-mypropylamino, di-n-butylamino, di- Me-butylamino, di-n-pentylamino, di-me-pentylamino, di-n-hexylamino, etc., preferably dimethylamino, N-ethyl-N-methylamino, diethylamino, etc.
4 alkylamino, etc. The C1-4 alkyl group represented by Rla and Rla is, for example, the one mentioned above for R1, and is preferably methyl, ethyl, or the like. The Cl-4 alkoxy group represented by Rla is, for example, the one described for R3 above, and is preferably methoxy, ethoxy, or the like. The chloropyridyl group represented by A8 and Ab is, for example, 2-chloro-3-pyridyl, 4-
Chloro-3-pyridyl, 5-chloro-3-pyridyl, 6
-chloro-3-pyridyl, 3-chloro-4-pyridyl and the like, preferably 6-chloro-3-pyridyl and the like. Pyridyl represented by Ab is 3-pyridyl,
4-pyridyl and the like, preferably 3-pyridyl.

In addition, representative α-unsaturated amines or salts thereof of the formula [l] include, for example, the formula [where xla is a hydrogen atom, Cl-4 alkoxycarbonyl or Cl-4 alkylsulfonylthiocarbamoyl, R80 is a hydrogen atom, cI-3anru, Cl-4alkyl, mono- or diCl-4alkoxy-CI-
*Alkyl, C? −. Aralkyl, mono- or di-C
1-4 alkylamino or C1-4 alkoxy, A
C represents 3- or 4-pyridyl, pyrazinyl or 4- or 5-thiazolyl which may be substituted with a halogen atom, CI-4 alkyl or C8-4 alkoxy, Rsa and Rtd are hydrogen, lower alkyl group,
A halogenated lower alkyl group or a C+-a acyl group,
n has the same meaning as above. α-unsaturated amines or salts thereof represented by the formula [wherein, alkylamino, N -C+-*alkyl-N-CI-3 acylamino, C7-5 aralkylamino, halogenothiazolyl-C1-, alkylamino or CI-a alkoxy-CI-1 alkylamino, R″0 is hydrogen Atom, Cl
-3 acyl, C1-4 alkyl, mono- or di-C1
-4 alkoxy-C1-4 alkyl, Cv-s aralkyl, mono- or di-Cl-4 alkylamino or C
I-4 alkokene, n is 0, lt or 2, Ad is a halogen atom, 3- or 4-pyridyl, pyrazinyl or 5-thiazolyl optionally substituted with c, -4 alkyl or C+-*alkoxy shows. α-unsaturated amines or salts thereof represented by the formula [wherein, -! Alkyl-N-formylamino, Rtd is a hydrogen atom, C
It represents a group represented by l-2 alkyl or Cl-3 acyl (HaI2 represents a halogen atom). ] Unsaturated amines or salts thereof, represented by the formula , R2
d is a hydrogen atom, formyl or C11 alkyl, A8
represents a group represented by (represents a formula atom).

] α-monounsaturated amines or salts thereof, 1eRt9 [wherein Rle is amino, mono- or di-C3-, alkylamino or N-C+-zalkyl-N-formylamino, R″8 is Cl -t-alkyl or formyl, Ha12 represents a halogen atom] or salts thereof.

In the Jia formula [1'] to [1i], X! a, X” and X
! A group represented by c, a group represented by R, Rr8 and R″d, a group represented by z, R20, Rld and R″8, Ac
, a group represented by Ad and Ao, a group represented by Rea, 1
The groups represented by 7a are the above-mentioned X′, R1, R″,
A, R", R?, etc. are used.

The compound represented by the general formula [11] or its salt can be produced by similar known methods, as well as by
It can also be produced by the method described in No. 192383.

(Left below) When Compound [1] is obtained in a free form, it may be formed into a salt using a conventional method, or the salt obtained as a salt may be converted into a free form using a conventional method. good. When compound [1] has an acidic group such as a carboxyl group, a sulfo group, or a phosphono group in X', Examples of the base include sodium, potassium, lithium, and calcium.

・Inorganic bases such as 7gnesium and ammonia, and organic bases such as pyridine, collidine, triethylamine, and triethanolamine are used. Also X'
, X'', R', R'' and A have a basic group such as an amino group or a substituted amino group, they may form an acid addition salt, and such acid addition salts include hydrochloride. , hydrobromide, hydroiodide, nitrate, sulfate, phosphate, acetate.

benzoate, maleate, fumarate, succinate,
Tartrates, citrates, oxalates, glyoxylates, aspartates, methanesulfonates, methanedisulfonates, 1,2-ethanedisulfonates, benzenesulfonates, and the like are used.

Formula [1] used in the active substance combination according to the invention
] Representative compounds of α-unsaturated amines include 1-[N-(6-chloro-3-pyridylmethyl)-N-
Methylcoamino-1-methylamino-2-nitroethylene, ,6-chloro-3-pyridylmethyl)amino-l-dimethylamino-2-nitroethylene, 1-[N-(6-chloro-3-pyridylmethyl) -N-ethylcoamino-1
-methylamino-2-nitroethylene, r-cN=(s-chloro-3-pyridylmethyl)-N-
methyl]amino-L-dimethylamino-2nitroethylene, 1-[N-(6-chloro-3-pyridylmethyl)-N
-ethylcoamino-,N-formyl-N-methyl)-2
-nitroethylene, 1-[N-(2-chloro-5-thiazolylmethyl)-N
-ethylcoamino-1-methylamino-2-nitroethylene, ! -[N-(2-chloro-5-thiazolylmethyl)]]
Amino-1-dimethylamino-2-nitroethylene, 1-[N-(6-bromo-3-pyridylmethyl)-N-
Methylcoamino-1-methylamino-2-nitroethylene, 1-[N-(6-chloro-3-pyridylmethyl)-N-
Formylcoamino! -dimethylamino 2-nitroethylene, 1-[N~(6-fluoro-3-pyridylmethyl)-N
-Methylcoamino-1-methylamino-2-nitroethylene, ! -IN-ethyl-N-(6-fluoro-3-pyridylmethyl)]]amino! -Methylamino-2nitroethylene 1-[N-(6-bromo-3-pyridylmethyl)-N-
Ethylcoamino-1-methylamino-2-nitroethylene, 1-[N-(2-chloro-5-thiazolylmethyl)-
N-methylcoamino-,N-formyl-N-methyl)amino-2-nitroethylene, 1-IN-(2-chloro-5-thiazolylmethyl)-N
-ethylcoamino-,N-formyl-N-methyl)amino-2-nitroethylene, 1-[N-(6-bromo-3-pyridylmethyl)-N-
Methylcoamino-,N-formyl-N-methyl)amino-2-nitroethylene, 1-4N-(6-bromo-3-pyridylmethyl)-N-
Ethylcoamino-,N-formyl-N-methyl)amino-2-nitroethylene, 1-[N-(6-bromo-3-pyridylmethyl)-N-
Formylcoamino-1-dimethylamino-2-nitroethylene, 1-[N-(6-chloro-3-pyridylmethyl)-N-
(2,2,2-trifluoroethyl)]]amino-1-
Methylamino-2-nitroethylene! -[N-(2-
Chloro-5-thiazolylmethyl)-N-formyl]amino! -dimethylamino-2-nitroethylene, ,6-chloro-3-pyridylmethyl)amino-1-methylamino-2-nitroethylene, l-amino-1-[N
-(6-chloro-3-pyridylmethyl)-N-methylcoaminonitronitroethylene and the like.

The above α-unsaturated amines or salts thereof and their use as insecticides were disclosed in Japanese Patent Application No. 63-19 by the present inventors.
It is described in No. 2383.

The following compounds may also be mentioned as one of the fungicides used in the active substance combination according to the invention.

(2) (Z)-2°-methylacetophenone-4°6-
Dimethylpyrimidin-2-ylhydrazone (Ferimsin), 4.5.6.7-Tetrachlorphthalide (Fusalide)
, 3-alkyloxy-1,2-benziisothiazole-
1,1-dioxide (probenazole), diisopropyl-1,3-dithiolane-2-ylidene malonate (
isobrothiolane), kasugamycin hydrochloride (kasugamycin), O-ethyl-S-diphenyldithiophosphate (nidifenphos), 03O-diisopropyl-6-benzylthiophosphate (ibrobenphos), 5-methyl-1°2.4-triazolo[ 3,4-b]benzothiazole (tridiclazole), validamycin A (validamycin), α, α, α-trifluoro-3-isopropoxy-〇-trianilide (
flutolanil), 3′-isopropoxy-2-methylbenzanilide (mepronil), ■-(4-chlorobenzyl)-1-cyclobenzyl 3
- Phenyl urea (benziclone), etc.

The above-mentioned fungicides, which are one component of the active substance combination according to the invention, are already known and are described, for example, in the above-mentioned Vestaside Manual.

The weight ratios of the active compounds of each group in the active substance combinations according to the invention are then generally: Active compounds of the active compound group of known fungicides under 2) can be used in an amount of o,t-100 parts by weight, preferably 0.5 to 50 parts by weight.

The active compound combinations according to the invention exhibit a strong insecticidal and fungicidal activity and can be used by foliar spraying, submerged or surface application, irrigation treatment on the soil surface, soil mixing treatment or nursery box treatment.

The active substance combination according to the present invention exhibits stronger insecticidal and fungicidal activity at a lower dose than when each active substance is applied alone, so that chemical damage to crops can be completely avoided, and compared with conventional insecticides or fungicides. Immediate effect, residual effect, systemic transferability, etc. may be unbalanced, or even if the insecticidal or bactericidal effect is excellent, it may be toxic to warm-hearted animals and fish, or may be unsafe to beneficial insects and natural enemies, or cause chemical damage to crops. It can be used even in situations where there are restrictions on its use due to problems.

The insecticidal and fungicidal composition of the present invention can control the following pests (diseases and pests).

For example, among insects, there is the Nephoptera leafhopper, which is a hemiptera pest of rice fields.
t 1ceps), planthoppers (Nil
aparvahia Lugens), white-legged planthopper (S.
ogatel 1afurucifera), brown-bottomed planthopper (Laodelphaxstriatellus)
Chilo 5 is a lepidopteran pest such as
uppressalis), Cnaph borer (Cnaph)
aloarocis medinalis), Naranga aenescens, etc., and the rice weevil (Lissorho), which is a Coleoptera pest.
Ptrus oryzaphilus), rice weevil (Echinocnemus squameus), rice weevil (Oulema oryzae), and other lepidopteran pests of horticultural crops such as fruit trees, cane, and tea.
PIuLelta maclipennis), Pieris brassicae, Armyworm moth (Mamestrabrass 1cae), Doxophy-es sp.
), Caloptilia theiv
ora), aphids (Myzus persicae, cotton aphid (Aphis gossyipii), apple aphid (＾phisponi), etc.), scale insects (Unaspis yanoe), etc., which are Hemiptera pests.
nsis), mulberry scale insect (Pseudoco
ccus coms Locki), whitefly (Trialeurodes vaporario), etc.), whitefly (Trialeurodes vaporario)
ru+++), Chanomidori leafhopper (Ea+po
asca onukii), green thrips (Scirtothrips dorsalis), and southern yellow thrips, which are pests of the order Thripsales. (Thrips pal++i)
, etc., the Colorado caterpillar (Lept.
inotarsa decemlineata), Epilachnavtgi
nLioctopunctata) and the like.

In addition, examples of plant pathogenic bacteria include archaeal fungi (^r-ch
imiseites), Phycomycetes
es), Ascoa+ycetes, Basidiomycetes, Deuteromycetes (F
However, as a representative example of the bactericidal spectrum of the above-mentioned plant diseases, for example, rice blast fungus (Pyricu-Iar.
ia oryzae), rice attack and defense fungi (Pellicu
laria 5a-sakii), and Rhizoctonia sola (Rhizo), a type of pathogen of vegetable seedling blight.
tionta 5olani), etc.

The active compound combination of the present invention can be in the form of a mixed preparation of a general agricultural chemical containing both components (1) or a salt thereof and (2), such as an emulsion, a wettable powder, a powder, a granule, a tablet, It can be in the form of a spray or the like, or it can be in the form of a conventional formulation, such as an emulsion or a wettable powder, in which components (1) or a salt thereof and (2) can be mixed together at the time of use.

These preparations are prepared by dissolving or dispersing the above (1) or a salt thereof or the active ingredient (2) alone or in a mixture in a suitable liquid carrier, or by mixing or adsorbing it with a suitable solid carrier, and as necessary. For example, emulsifiers, suspending agents, spreading agents,
It can be produced by a known method by adding penetrating agents, wetting agents, mucilage agents, stabilizers, etc.

The content ratio of all active ingredients in the preparation varies depending on the purpose of use, but for emulsions, wettable powders, etc., it is suitable to be about 5 to 70% by weight, and for powders, it is suitable to be 0.1 to 10% by weight.
The appropriate concentration for the granules is 0.5 to 1G by weight, or these concentrations may be changed as appropriate depending on the purpose of use.

When using emulsions, wettable powders, etc., they are suitably diluted with water or the like to increase the amount (for example, 100-to, ooo times) and then sprayed.

Examples of liquid carriers (solvents) used include water, alcohols (e.g., methyl alcohol, ethyl alcohol, n-propyl alcohol, isopropyl alcohol,
ethylene glycol, etc.), ketones (e.g., acetone, methyl ethyl ketone, etc.), ethers (e.g., dioxane, tetrahydrofuran, ethylene glycol monomethyl ether, propylene glycol monomethyl ether, etc.), aliphatic hydrocarbons (e.g., kerosene, kerosene, fuel oil, etc.), aromatic hydrocarbons (e.g. benzene,
Toluene, xylene, solvent naphtha, methylnaphthalene, etc.), halogenated hydrocarbons! I (e.g., dichloromethane, chloroform, carbon tetrachloride, etc.), acid amides (e.g., dimethylformamide, dimethylacetamide, etc.), ester II (e.g., ethyl acetate, butyl acetate, fatty acid glycerin ester, etc.), nitriles (e.g., Solvents such as acetonitrile, propionitrile, etc.) are suitable, and these can be used alone or in a mixture of two or more in an appropriate ratio.

Solid carriers (diluents and bulking agents) include vegetable powders (e.g., lactose, soybean flour, tobacco powder, wheat flour, wood flour, etc.), mineral powders (e.g., kaolin, bentonite, clays such as acid clay, and talc). , silicas such as mica powder, etc.), diatomaceous earth, calcium carbonate, alumina, sulfur powder, activated carbon, etc., and these can be used alone or in a mixture of two or more in an appropriate ratio.

Surfactants used as emulsifiers, spreaders, penetrants, dispersants, etc. may include soaps, polyoxyethylene alkyl allyl ethers [e.g.
E.N. (E-A) 142; Daiichi Kogyo Seiyaku Co., Ltd.
(manufactured by Toho Chemical Co., Ltd.), alkyl sulfates (e.g., Emar IO, Emar 40; manufactured by Kao (Aji)), alkyl sulfonates (e.g., Neogen, Neogen T: Dai-Kogyo Seiyaku Co., Ltd.) Polyethylene glycol ethers [for example, Noniball 85, Noniball 100, Danibormi 60; manufactured by Sanyo Kasei (Mai)], polyhydric alcohol esters [for example, Toween 20, Toween 80; Nonionic and anionic surfactants such as those manufactured by Kao (Aji) are used as appropriate.

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, fungicides, acaricides,
It can also be used as a mixture with nematicides, fungicides, and growth regulators.

The insecticidal and fungicidal composition of the present invention thus obtained has extremely low toxicity, is safe, and is an excellent agrochemical.

The insecticidal and fungicidal composition of the present invention can be used in the same manner as conventional insecticides and fungicides, and as a result, it can exhibit superior effects compared to conventional products. for example,
The insecticidal and fungicidal composition of the present invention can be used against target pests by, for example, spraying on leaves of crops treated with seedling boxes, spraying insect bodies, applying in water to rice fields, or treating soil. The application amount can vary widely depending on the application time, application location, application method, etc.; - For boat fishing, the active ingredient (compound (1) or its salt and known fungicides) per hectare; It is desirable to apply so that the amount is 0.39 to 300G9, preferably 509 to 1000g. In addition, when the insecticidal and fungicidal composition of the present invention is a wettable powder, the final concentration of the active ingredient is 0.1-1000 pl)n.
Preferably, it may be used after being diluted to a range of tO to 500 ppm.

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] The example is a test of the control effect on brown planthopper and rice blast by spraying the liquid on the leaves.Solvent: Mixed solution of acetone (3.5 parts by weight) and dimethylformamide (3.5 parts by weight) 7.0 parts by weight Emulsifier : Polyhydric alcohol ester (Tween 20; manufactured by Kao Corporation) 2.0 parts by weight Active compound mixture listed in the column of test drugs in Table 1 below 1.0 parts by weight of the active compound alone is mixed with a solvent containing the above emulsifier, and the mixture is mixed with a spreading agent (Dyne@
) It was diluted to the specified concentration with tap water for 3000 times.

■Test against brown planthopper (spraying test) Test method: Rice plants with a plant height of 30co+ planted in PVC pots with a diameter of 11.3ci+ (20 days after transplanting) are inoculated with 20 brown planthopper 3rd to 4th instar larvae per pot. A cylinder made of transparent vinyl chloride film with a diameter of 11 cm + a and a height of 67 cm was placed over the cylinder (the upper opening was covered with goose), and a water dilution of the above active compound at a predetermined concentration prepared on the next day was sprayed onto the cylinder. 2 per pot using gun
0yt (l) Sprayed from the opening, placed in a glass constant temperature room at 25 ± 1℃, checked the number of surviving insects after 2 days, and determined the insecticidal rate [=((
Number of test animals - surviving insects lost)/number of test animals)xtOO] was calculated. The test was conducted in duplicate.

■ Test for control effect on rice blast disease (spraying test) Test method: Using a spray gun, a water dilution of the above active compound at a predetermined concentration was applied to rice plants planted in PVC pots with a diameter of 9.0 cm 32 days after sowing. After one day, the rice blast disease spores were naturally infected from the rice blast disease-damaged leaves at a temperature of 25 ± 2° and a relative humidity of 100.
After keeping it at room temperature for 2 days, it was transferred to a glass greenhouse at a temperature of 25 ± 2°, and after 5 days, the percentage of lesion area per plant (%) was inoculated.
The degree of morbidity is classified by investigating the disease, and the control value (%
) was sought. The test was conducted in duplicate.

Degree of disease Spot area ratio (%) 0 0.5 Less than 2 l 2 to less than 5 2 5 to less than 20 3 10 to less than 20 4 20 to less than 40 5 40 or more control value (%) = ((Untreated area The disease severity level - disease severity level in treated area)/(severity level in non-treated area) x100 results are shown below.

(Margin below) Table 1 Note) 10 Compounds of formula [1] used in the test: Compound No.
1 : 1 [N-(6-chloro-3-pyridylmethyl)-N-methylcoamino-1-methylamino-2-
Nitroethylene compound No, 2 + 1- [N -(6-chloro-3
-pyridylmethyl)-N-ethyl)coamino-,N-formyl-N-methyl)-2-nitroethylene compound No.
, 3: l-[N-(6-chloro-3-pyridylmethyl)-N-ethylcoamino-1-methylamino-2
-Nitroethylene compound No. 4: 1-[N-(2-chloro-5
-thiazolylmethyl)amino-! -dimethylamino 2
-Nitroethylene compound No. 5: l -[N-(6-chloro-5
-thiazolylmethyl)-N-formylcoamino-t-dimethylamino-2-nitroethylene 2, Known compounds used in this test: Compound (A): Ferimzone compound (B); Tridicrazole compound (C): Kasugaminone Example 2 Preparation of test agent for control effect on brown planthopper and rice blast by treatment of granules in seedling box: 6 parts by weight of the active compound mixture or the active compound listed in the column of test agent in Table 2 below. Add 89 to 93 parts by weight of clay to 2 (or even 4) parts by weight of sodium lignin sulfonate, grind and mix the total amount to 100 parts by weight, and add a small amount of water. After kneading, the mixture was extruded, granulated, and dried to produce granules.

Test method: 509 of each of the above granules per box was sprinkled on rice seedlings planted in paddy rice seedling boxes 3 weeks after sowing, and the next day, 11,3
The plants were transplanted into vinyl chloride pots with a diameter of 1.5 cm and left in a glass greenhouse at 25±1°C. Three weeks after transplantation, 20 brown planthopper larvae (male to male ratio 1:1) were inoculated into each pot and placed in a cylinder made of transparent vinyl chloride film with a diameter of 11 cm and a height of 67 CI11 (the upper opening was covered with goose). ), check the number of surviving plants after 2 days, and check the insect killing rate [=((number of test animals - number of surviving animals)/number of test animals) x 1oO]
I asked for

Rice plants after the insecticidal test (24 days after transplanting, rice blast disease pathogenic bacteria was naturally infected from leaves damaged by rice blast disease, and the temperature was 25±
After keeping the inoculation room temperature at 2° and 100% relative humidity for 2 days,
The seeds were transferred to a glass chamber at a temperature of 25±2°, and after 5 days, the percentage of lesion area per taste (%) was investigated to classify the degree of disease, and the control (i [II (%)) was calculated using the following formula. Each test was conducted in duplicate.

Degree of disease Spot area ratio (%) 0 Less than 0,652 1 2 to less than 5 2 5 to less than 3 10 to less than 20 4 20 to less than 40 5 More than 40 control value (%) = ((Mobility of untreated plot - Morbidity of treated plot)/(Sickness of non-treated plot))X100 The results are summarized below.

Table 2 Note) 1. Compound of formula [1F: Compound No.] used in this test
1: l-[N-(6-chloro-3-pyridylmethyl)-N-methylcoamino-1-methylamino-2-
Nitroethylene compound No. 2: l-[N-(6-chloro-3
-pyridylmethyl)-N-ethylcoamino-,N-formyl-N-methyl)-2-nitroethylene compound No.
3: l-[N-(6-chloro-3-pyridylmethyl)-N-ethylcoamino-1-methylamino-2-
Nitroethylene compound No. 4: l-[N-(2-chloro-5
-thiazolylmethylcoamino-l-dimethylamino-2
-Nitroethylene compound No. 5: 1-[N-(6-chloro-5
-thiazolylmethyl)-N-formyl]amino! -Dimethylamino-2-nitroethylene 2, known fungicides used in this test: Compound (A): ) Lycyclazole Compound (B): Probenazole Example 3 Control of brown planthopper and rice sheath blight by spraying liquid on rice foliage Effect test Solvent: Mixed solution of acetone (3.5 parts by weight) and dimethylformamide (3.5 parts by weight) 7.0 parts by weight Emulsifier: Polyhydric alcohol ester (Tween 20: manufactured by Kao (Aji)) 2.0 parts by weight The active compound mixture described in the column of test drugs in Table 3 below is prepared by mixing 1.0 parts by weight of the active compound alone with a solvent containing the above emulsifier, and adding the mixture to a spreading agent (Dyne).・
) It was diluted to the specified concentration with tap water for 3000 times.

■Test method for brown planthopper; Inoculate 20 brown planthopper 3rd to 4th instar larvae per pot into 30cm tall rice plants (20 days after transplanting) planted in PVC pots with a diameter of 11.3cm. A cylinder made of transparent vinyl chloride film with a height of 67 cm was covered with a cylinder (the upper opening was covered with goose), and a spray gun was used to spray a diluted solution of the above active compound in water at a predetermined concentration, prepared on the next day. 20 per pot using
Sprayed through the village opening, placed in a glass constant temperature room at 25 ± 1°C, counted the number of surviving plants after 2 days, and calculated the insecticidal rate = ((number of tested animals - number of surviving plants) / number of tested animals) x 100] . The test was conducted in duplicate.

■ Control effect test against rice disease 1/5000 a PVC pot was flooded with rice at the panicle formation stage, and a pre-prepared water dilution of the above active compound at a predetermined concentration was applied using a spray gun. Spray 1 ooj + I2 per pot, and the day after spraying, test rice plants are inoculated with sheath blight fungi that have been cultured for 2 days on potato agar medium, and the temperature is 28-30° and the relative humidity is 95.
% or more for 10 days to cause Monkei disease to develop, the degree of disease onset was investigated, and the control value (= (100
− Damage symptoms)) were sought. The test was conducted in two series.

Damage - ((3n3+2nt+n, +no) / 3N
) X 100 However, N2 total number of stems investigated: No disease-free stems, number of stems infected up to the second lower first leaf sheath.

n,: Stems affected up to the lower third leaf position or higher.

n,: Stem rot with disease up to the lower third leaf position or higher.

The results are summarized below.

Table 3 Note) 1. Compound of general formula [1] used in this test: Compound N
o, l: 1-[N-(6-chloro-3-pyridylmethyl)-N-methylcoamino-1-methylamino-
2-nitroethylene compound No. 2: l-[N-(6-chloro-3
-pyridylmethyl)-N-ethylcoamino-,N-formyl-N-methyl)-2-nitroethylene compound No.
3: l-” [N (6-chloro-3-pyridylmethyl)-N-ethylcoamino-1-methylamino-
2-nitroethylene compound No. 4: l -[N (2-chloro-5
-thiazolylmethyl)amino-1-dimethylamino-2
-Nitroethylene compound No. 5: 1- [N (6-chloro-5
-thiazolylmethyl)-N-formylcoamino-l dimethylamino-2-nitroethylene 2, known bactericides used in this test: Compound (A): Validamycin A Compound (B): Flutolanil No. 1.2 and 3 above The table shows that the insecticidal and fungicidal composition of the present invention has excellent cooperative insecticidal and fungicidal action, fast-acting properties, and residual effects against brown planthopper, brown planthopper, rice blast, and rice sheath blight compared to the use of each active ingredient alone. It is proven to be effective.

Example 4 (Wettable powder) Compound No. 1 (5% by weight) shown in Example 1, Compound (A) (20% by weight), sodium lignisone sulfonate (5% by weight), polyoxyethylene glycol ether ( Nonipole 85' (5% by weight), white carbon (10% by weight), and wettable powder clay (55% by weight) were thoroughly mixed to produce a wettable powder.

Example 5 (hydrating agent) Compound No. 3 shown in Example 3 (5% by weight), compound (A) (15% by weight), polyoxyethylene glycol ether (Nomiball 85': 5% by weight), White carbon (10% by weight), clay for wettable powders (60% by weight)
) were mixed well to produce a wettable powder.

Example 6 (powder) Compound No. 1 shown in Example 1 (0.25% by weight), compound (A) (2.0% by weight), white carbon (5.0% by weight), clay (92% by weight) , 75% by weight) were thoroughly mixed to produce a powder.

Example 7 (powder) Compound No. 3 shown in Example 3 (0.25% by weight), compound (A) (0.3% by weight), white carbon (5.0% by weight), clay (94% by weight) , 45% by weight) were thoroughly mixed to produce a powder.

Claims (1)

[Claims] 1. (1) Formula [1] ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ [1] [In the formula, one of X^1 and X^2 is an electron-withdrawing group, and the others are hydrogen Atom or electron-withdrawing group, R^1 is a group via a nitrogen atom, R^2 is a hydrogen atom or a group via a carbon, nitrogen or oxygen atom, n is 0, 1 or 2, A is a heterocyclic group Or represents a cyclic hydrocarbon group. However, R^1 is β-N-
When pyrrolidinoethylamino and R^2 is a hydrogen atom, A is represented by the formula ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ or ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (Hal indicates a halogen atom) Indicates the group that can be used. ] At least one α-unsaturated amine or its salt represented by (2) (Z)-2′-methylacetophenone-4,6-
Dimethylpyrimidin-2-ylhydrazone, 4,5,6
, 7-tetrachlorophthalide, 3-alkyloxy-1,2-benziisothiazole-
1,1-dioxide, diisopropyl-1,3-dithiolane-2-ylidene-
malonate, kasugamycin hydrochloride, O-ethyl-S,S-diphenyldithiophosphate, O,O-diisopropyl-S-benzylthiophosphate, 5-methyl-1,2,4-triazolo[3,4-d]benzo Thiazole, validamycin A, α,α,α-trifluoro-3'-isopropoxy-O
-toluanilide, 3'-isopropoxy-2-methylbenzanilide, 1-(4-chlorobenzyl)-1-cyclobenzyl-3
- At least one compound selected from the group consisting of phenylurea.