JPH1129418A - Insecticidal composition for agricultural and horticultural use - Google Patents

Abstract

(57) [Problem] To provide an excellent insecticide and fungicide. SOLUTION: Formula [1] [In the formula, ^one of X ¹ and X ² is an electron-withdrawing group, the other is a hydrogen atom or an electron-withdrawing group, R ¹ is a group via a nitrogen atom, and R ² is a hydrogen atom or a carbon, nitrogen or oxygen atom. And n represents 0, 1 or 2, and A represents a heterocyclic group or a cyclic hydrocarbon group. However, when R ² is β-N-pyrrolidinoethylamino and R ² is a hydrogen atom, A is represented by the formula: (Hal represents a halogen atom). And at least one of the α-unsaturated amines or salts thereof represented by the following formula (2): ferrimzone, fusalide,
Probenazole, isoprothiolane, kasugamycin,
Edifenphos, iprovenphos, tricyclazole,
A pesticidal fungicidal composition for agricultural and horticultural use, comprising at least one compound selected from the group consisting of validamycin, flutolanil, mepronil, penciclone and the like.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

TECHNICAL FIELD The present invention relates to an α-formula represented by the following formula [1]:
The present invention relates to a novel insecticide for agricultural and horticultural use which exhibits an excellent insecticidal and fungicidal action comprising a combination of an unsaturated amine or a salt thereof and a known fungicide.

[0002]

2. Description of the Related Art Conventionally, various chemicals such as organophosphorus, carbamate and pyrethroids have been developed as agricultural and horticultural insecticides and used as single agents and mixed agents. However, conventional insecticides lack the balance of insecticidal spectrum, insecticidal activity at each stage of development of the insect pest, fast-acting, residual-effect, systemic migration, etc. Alternatively, due to problems such as safety against useful insects and natural enemies, and phytotoxicity to crops, the use scene, the number of times of use and the like are limited, so that it cannot be said that satisfactory insecticidal effects are necessarily obtained. In particular, recently, pests with reduced susceptibility to various conventional chemicals, for example, black leafhoppers and planthoppers that are resistant to organophosphates and carbamates in rice fields in Japan have emerged, and a technique for controlling these pests has been established. Is strongly requested. A similar situation has been observed in the field of fungicides, especially in recent years, because the blast pathogens of rice or rice sheath blight pathogens have become less sensitive to conventional insecticides, making it difficult to control them. Establishment is strongly demanded. Further, in recent years, so-called cost reduction has also been strongly demanded for the control of these pests, and it is necessary to achieve a high control effect with a small number of treatments and a small amount of dropped drug, and there is a demand for the development of a drug which can meet these demands. . In recent years, as one of Japan's paddy rice cultivation techniques, mechanical transplantation of seedlings has become widespread, and as a result, not only conventional drug treatment in paddy main fields but also nursery box treatment before transplantation of drugs or There is a strong demand for the development of an excellent drug capable of controlling pests by applying a lateral streak at the time of transplantation, that is, a drug exhibiting excellent medicinal properties and having no harm.
It is already known that the following fungicides have activity to control rice blast or rice sheath blight. For example,
(Z) -2′-methylacetophenone-4,6-dimethylpyrimidin-2-ylhydrazone (ferimzone),
4,5,6,7-tetrachlorophthalide (fusalide), 3-alkyloxy-1,2-benzisothiazole-1,1-dioxide (probenazole), diisopropyl-1,3-dithiolan-2-ylidene- Malonate (isoprothiolane), kasugamycin hydrochloride (kasugamycin), O-ethyl-S, S-diphenyldithiophosphate (edifenphos), O, O-diisopropyl-S-benzylthiophosphate (iprobenphos), 5-methyl-1,2,2 4-triazolo [3,4-
b] Benzothiazole (tricyclazole) and the like are used as agents for controlling rice blast and the like, and for example, validamycin A (validamycin), α, α, α-trifluoro-3
-Isopropoxy-O-toluanilide (flutranyl), 3'-isopropoxy-2-methylbenzanilide (mepronil), 1- (4-chlorobenzyl) -1-
Cyclopentyl-3-phenylurea (pencyclon) and the like are used as a controlling agent for rice sheath blight and the like. The Pesticide Manual, 8th edition, 1987, The Britis
h Crop Protection Concil).

[0003]

However, the actions of the above-mentioned known insecticidal compounds and fungicidal compounds alone exhibit only an insecticidal effect or a fungicidal effect, respectively. Cannot be controlled at the same time. On the other hand, the present inventors have found that unsaturated amines of the following formula [1] or salts thereof are effective as insecticides, and filed a patent application (Japanese Patent Application No. 63-192383).
issue). In examining the more effective use of the unsaturated amines, as a result of studying the combination with the above-mentioned known fungicidal compounds, a cooperative insecticidal fungicidal effect that cannot be obtained by using both alone is obtained, and It was found that it was satisfactory in terms of toxicity.

[0004]

According to the present invention, (1)
Equation [1]

Embedded image [In the formula, ^one of X ¹ and X ² is an electron-withdrawing group, the other is a hydrogen atom or an electron-withdrawing group, R ¹ is a group via a nitrogen atom, and R ² is a hydrogen atom or a carbon, nitrogen or oxygen atom. And n represents 0, 1 or 2, and A represents a heterocyclic group or a cyclic hydrocarbon group. However, when R ¹ is β-N-pyrrolidinoethylamino and R ² is a hydrogen atom, A is represented by the formula

Embedded image (Hal represents a halogen atom). And (2) (Z) -2′-methylacetophenone-4,6-dimethylpyrimidin-2-ylhydrazone (ferimzone), 4,5, 6,7-tetrachlorophthalide (fusalide), 3-alkyloxy-1,
2-benzoisothiazole-1,1-dioxide (probenazole), diisopropyl-1,3-dithiolane-
2-ylidene-malonate (isoprothiolane), kasugamycin hydrochloride (kasugamycin), O-ethyl-
S, S-diphenyldithiophosphate (edifenphos), O, O-diisopropyl-S-benzylthiophosphate (iprobenphos), 5-methyl-1,2,4
-Triazolo [3,4-d] benzothiazole (tricyclazole), validamycin A (validamycin),
α, α, α-trifluoro-3′-isopropoxy-O
-Tolanilide (flutranil), 3'-isopropoxy-2-methylbenzanilide (mepronil), 1-
An insecticidal fungicidal composition for agricultural and horticultural use, characterized by containing at least one compound selected from the group consisting of (4-chlorobenzyl) -1-cyclopentyl-3-phenylurea (pencyclon) and the like. You.

[0005] The insecticidal and / or fungicidal activity of the insecticidal and fungicidal composition of the present invention in which the above-mentioned known fungicide is blended with the α-unsaturated amines of the formula [1] or a salt thereof is determined by the effect of each active compound. It is clearly larger than the sum of and has excellent synergistic effects, and has excellent fast-acting and residual effects.
In particular, the insecticidal fungicidal composition according to the present invention is applied for the purpose of controlling pests (diseases and pests) on agricultural crops, for example, Hemiptera leafhoppers and planthoppers, which are important pests of rice, such as Hemiptera (E.g., brown planthopper, brown planthopper) and Coleoptera pest rice weevil, rice dwarf beetle, and rice blast or rice sheath blight, which are important pathogens of paddy rice, in a lower concentration and cooperative insecticidal activity than when only a single active compound is used. Shows bactericidal activity, and has excellent fast-acting and residual effects.

In the above formula [1], ^one of X ¹ and X ² represents an electron-withdrawing group and the other represents a hydrogen atom or an electron-withdrawing group. Examples of the electron-withdrawing group represented by X ¹ and X ² include cyano , Nitro, alkoxycarbonyl (e.g., _C1-4 alkoxy-carbonyl such as methoxycarbonyl, ethoxycarbonyl, etc.), hydroxycarbonyl, _C6-10 aryl-oxycarbonyl (e.g., phenoxycarbonyl, etc.), heterocyclic oxycarbonyl (as a heterocyclic group Are used, for example, pyridyloxycarbonyl, thienyloxycarbonyl, etc.), for example, C _1-4 alkylsulfonyl optionally substituted with halogen or the like (eg, methylsulfonyl, trifluoromethylsulfonyl, ethylsulfonyl, etc.) , Aminosulfonyl, di-C _1-4 alkoxyphosphoryl (for example, diethoxyphosphoryl) ), For example, C _1-4 acyl _optionally substituted with halogen (eg, acetyl, trichloroacetyl, trifluoroacetyl, etc.), carbamoyl, C _1-4 alkylsulfonylthiocarbamoyl
(Eg, methylsulfonylthiocarbamoyl) and the like. One of X ¹ and X ² may represent a halogen atom such as fluorine, chlorine, bromine and iodine, and X ¹ and X ²
Is bonded together with adjacent carbon

Embedded image And the like may be formed. formula

Embedded image Preferred examples of the group represented by are, for example, O ₂ NCH = and the like.

In the above formula [1], R ¹ represents a group via a nitrogen atom.

Embedded image And the like represented by Here, R ⁶ is a hydrogen atom, an alkyl (eg, methyl, ethyl, n-propyl,
C such as i-propyl, n-butyl, i-butyl, n-hexyl
_1-6 alkyl), C _{6 -10} aryl (e.g. phenyl, etc.), aralkyl (e.g. C _7-9 aralkyl such as benzyl), those Hajime Tamaki (e.g. below, specifically pyridyl), C
_1-4 acyl (eg, formyl, acetyl, propionyl, etc.), C _6-10 aryl-carbonyl (eg, benzoyl, etc.), alkoxycarbonyl (eg, C _1-4 alkoxycarbonyl such as methoxycarbonyl, ethoxycarbonyl, etc.), C _6-10 Aryl-oxycarbonyl (for example, phenoxycarbonyl and the like), heterocyclic oxycarbonyl (the following are used as the heterocyclic group, for example, furyloxycarbonyl and the like), C _6-10 arylsulfonyl (for example, phenylsulfonyl and the like), alkyl Sulfonyl (for example, C _1-4 alkylsulfonyl such as methylsulfonyl), dialkoxyphosphoryl (for example, di-C _1-4 alkoxyphosphoryl such as diethoxyphosphoryl), alkoxy (for example, methoxy, C _1-4 alkoxy such as ethoxy), Hydroxy, amino, dialkylamino (e.g. dimethyl Mino,
Di-C _1-4 alkylamino such as diethylamino), acylamino (eg C _1-4 acylamino such as formylamino, acetylamino, propionylamino), alkoxycarbonylamino (eg C _1-4 alkoxy-carbonyl such as methoxycarbonylamino) Amino), alkylsulfonylamino (for example, C
_1-4 alkylsulfonylamino), dialkoxyphosphorylamino (for example, di- _C1-4 alkoxyphosphorylamino such as diethoxyphosphorylamino), _C7-9 aralkyloxy (for example, benzyloxy, etc.), alkoxycarbonylalkyl (for example, methoxy C _1-4 alkoxy carbonyl methyl, etc. - shows a carbonyl -C _1-4 alkyl) or the like, R ⁷ is a hydrogen atom, 1 to 3 substituents (e.g. hydroxy, C _1-4 alkoxy methoxy, etc., such as fluorine Halogen such as di-C _1-4 alkylamino such as dimethylamino, C _1-4 alkylthio such as i-propylthio, n-propylthio, C _1-3 acylamino such as acetylamino, C _1-4 such as methylsulfonylamino, etc. Tri-C _1-4 alkylsilyl such as alkylsulfonylamino and trimethylsilyl, for example pyridyl optionally substituted by halogen and the like Or thiazolyl) (e.g., C _1-4 alkyl such as methyl and ethyl), cycloalkyl (e.g., C _3-6 cycloalkyl such as cyclohexyl), alkenyl (e.g., C _3-6 such as vinyl and allyl). _2-4 alkenyl), cycloalkenyl (for example C _3-6 cycloalkenyl such as cyclohexenyl) or alkynyl (for example C _2-4 such as ethynyl)
Alkynyl) and the like. Further, R ⁶ and R ⁷ are bonded together with an adjacent nitrogen atom, for example,

Embedded image Or a 5- or 6-membered cyclic amino group. R ¹
Preferred examples of the group through the in nitrogen atoms indicated, for example (e.g. the R ^6, alkyl such as described in R ^7, aryl, aralkyl, heterocyclic group, acyl, alkoxycarbonyl, aryloxycarbonyl, heterocyclic oxycarbonyl, Arylsulfonyl, alkylsulfonyl, dialkoxyphosphoryl, cycloalkyl, alkenyl, cycloalkenyl, alkynyl, etc.)
(Especially di -C _1-6 alkylamino, N-C _1-6 alkyl -
Disubstituted amino, such as N- formylamino, monosubstituted amino and mono- -C _1-6 alkylamino, unsubstituted amino), alkyl such as described in (for example, the following R ^3, acyl, alkoxycarbonyl, alkylsulfonyl, di Hydrazino which may be substituted (e.g., alkoxyphosphoryl, etc.) (e.g., alkyl, aralkyl, etc. as described for R ³ below)
And hydroxyamino which may be substituted. Specifically, the expression

Embedded image (R ⁶ and R ⁷ have the same meanings as described above) and the like are frequently used as R ¹ .

R ² represents a hydrogen atom or a group via a carbon, nitrogen or oxygen atom. Examples of the group via a carbon atom represented by R ² include C _1-3 acyl (eg, formyl, acetyl, propionyl, etc.) and alkyl (eg, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-
Butyl, sec-butyl and the like C _1-4 alkyl), alkenyl (for example, C _2-4 alkenyl such as vinyl and allyl), and cycloalkyl (for example, C ₄ alkyl such as cyclopentyl and cyclohexyl)
_3-6 cycloalkyl), C _6-10 aryl (such as phenyl), aralkyl (such as C _7-9 aralkyl such as benzyl), a heterocyclic group having a bond at a carbon atom (for example, Specifically, a 3- or 4-pyridyl group, etc.)
And the like. These groups have 1 to 3 substituents (for example, C _1-4 alkylthio such as methylthio, ethylthio, etc.).
C _1-4 alkoxy such as methoxy and ethoxy, methylamino,
Mono or di-C _1-4 alkylamino such as dimethylamino, C _1-4 such as methoxycarbonyl, ethoxycarbonyl, etc.
(C _1-4 alkylsulfonyl such as alkoxy-carbonyl, methylsulfonyl, ethylsulfonyl, halogen such as fluorine, chlorine, bromine, iodine, C _1-4 acyl such as acetyl, benzoyl, phenylsulfonyl, pyridyl, etc.) You may. As a group via a nitrogen atom represented by R ² ,
For example kimono or the like is used each time as described above R ^1.
Examples of the group via an oxygen atom represented by R ² include alkoxy (for example, C _1-4 alkoxy such as methoxy and ethoxy), cycloalkoxy (for example, C _3-6 cycloalkoxy such as cyclohexyloxy), alkenyloxy (for example, vinyloxy , C _2-4 alkenyloxy, such as allyloxy), C _3-6 cycloalkenyloxy such cycloalkenyloxy (e.g. cyclohexenyl oxy), alkynyloxy (e.g. ethynyloxy etc.), C _6-10 aryloxy (e.g., phenoxy ), Heterocyclic oxy (the following are used as the heterocyclic group, for example, thienyloxy), a hydroxyl group and the like are used, and these have 1 to 3 substituents (for example, fluorine, chlorine, halogen such as bromine, Phenyl). Preferred examples of R ² include carbon,
A group via a nitrogen or oxygen atom, for example, formyl, (for example, C _1-4 alkylthio, C _1-4
Alkoxy, mono- or di-C _1-4 alkylamino, C _1-4
Alkoxy - carbonyl, C _1-4 alkylsulfonyl, fluorine, halogens such as chlorine, acetyl, benzoyl, phenylsulfonyl, pyridyl and the like) which may be substituted C _1-4 alkyl (especially methyl, ethyl, etc. C _{1- 4} alkyl, etc.), optionally substituted amino (for example, amino optionally substituted as described above for R ¹ ), (for example, the above-mentioned C _1-4 alkyl, C _3-6 cycloalkyl, C _{2 -4} alkenyl, C _3-6 cycloalkenyl, C _2-4 alkynyl, C _6-10 aryl, heterocyclic group, etc.) which may be substituted (e.g., C _1-4 alkoxy such as methoxy, etc.) is there.

N represents 0, 1 or 2. Therefore, -C _n H _2n of formula (1) - is a single _{bond, -CH 2 -, - CH 2} C
H ₂ —, —CH (CH ₃ ) —, but a single bond or —C
H ₂ -is frequently used. A is a heterocyclic group (for example, one or three of the following substituents, in particular, the following substituents (i), (iv), (viii), (xvii), (xLvi), (xLviii), etc. And the like, specifically, 3-pyridyl, 6-chloro-3-pyridyl, 6-
Methoxy-3-pyridyl, 6-methyl-3-pyridyl, 6
-Bromo-3-pyridyl, 6-fluoro-3-pyridyl,
2-chloro-5-thiazolyl, 4-pyridyl, 2-pyrazinyl, 2-thiazolyl, 4-thiazolyl, 3-quinolyl, etc.)
And A is further a cyclic hydrocarbon group (for example, a cyclic hydrocarbon group which may be substituted by one or two of the following substituents (xvii), for example, Cyclopropyl, cyclohexyl, phenyl, p-chlorophenyl, etc.). Preferred examples of the heterocyclic group represented by A include, for example, 3-pyridyl, 4-pyridyl, 6-chloro-3-pyridyl, 6-bromo-3-pyridyl, 6-fluoro-3-pyridyl, 2-chloro-5 Pyridyl or thiazolyl which may be substituted, such as thiazolyl; Preferred examples of the cyclic hydrocarbon group represented by A include, for example, halogenophenyl such as p-chlorophenyl. Examples of the alkyl, cycloalkyl, alkenyl, cycloalkenyl, alkynyl, aryl, aralkyl, aralkyl, heterocyclic group, and cyclic hydrocarbon group in the definition of X ¹ , X ² , R ¹ , R ² , R ⁶ , R ⁷ and A are as follows. The following groups can be used, and these groups may have 1 to 5 substituents such as the following (i) to (Lii). The alkyl preferably has 1 to 20 carbon atoms, and has 1 to 8 carbon atoms.
Are more preferred. The alkyl may be linear or branched. Specific examples of the alkyl include, for example, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl, hexyl, heptyl, octyl, nonyl, 2-ethylhexyl, decyl, undecyl, dodecyl, tridecyl ,
Tetradecyl, pentadecyl, hexadecyl, octadecyl, nonadecyl, eicosyl and the like are used. As the cycloalkyl, one having 3 to 6 carbon atoms is preferable, and for example, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl and the like are used. The alkenyl is preferably one having 2 to 6 carbon atoms. Specific examples of the alkenyl include, for example, vinyl, allyl (ally
l), isopropenyl, methallyl, 1,1-dimethylallyl,
2-butenyl, 3-butenyl, 2-pentenyl, 4-pentenyl, 5-hexenyl and the like are used. As the cycloalkenyl, those having 3 to 6 carbon atoms are preferable, and specific examples thereof include, for example, 1-cyclopropenyl, 2
-Cyclopropenyl, 1-cyclobutenyl, 2-cyclobutenyl, 1-cyclopentenyl, 2-cyclopentenyl,
3-cyclopentenyl, 1-cyclohexenyl, 2-cyclohexenyl, 3-cyclohexenyl, 1,3-cyclohexadien-1-yl, 1,4-cyclohexadiene-1
-Yl, 1,3-cyclopentadien-1-yl, 2,4-
Cyclopentadien-1-yl and the like are used. The alkynyl preferably has 2 to 6 carbon atoms, and specific examples thereof include, for example, 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 and the like are used. As the aryl, for example, phenyl, naphthyl and the like are used. As aralkyl, for example, benzyl, phenylethyl, naphthylmethyl and the like are used. 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. -Thienyl, 2- or 3-furyl, 2- or 3-pyrrolyl, 2-, 3- or 4-pyridyl, 2-, 4- or 5-oxazolyl,
2-, 4- or 5-thiazolyl, 3-, 4- or 5-
Pyrazolyl, 2-, 4- or 5-imidazolyl, 3-, 4
-Or 5-isoxazolyl, 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, 1,2,4
-Triazolyl, 1H- or 2H-tetrazolyl, N-
Oxide-2-, 3- or 4-pyridyl, 2-, 4- or 5-pyrimidinyl, N-oxide-2-, 4- or 5-pyrimidinyl, 3- or 4-pyridazinyl, pyrazinyl, N-oxide-3 -Or 4-pyridazinyl, benzofuryl, benzothiazolyl, benzoxazolyl, triazinyl, oxotriazinyl, tetrazolo [1,5-b] pyridazinyl, triazolo [4,5-b] pyridazinyl, oxoimidazinyl, dioxo Triazinyl, pyrrolidinyl, piperidinyl, pyranyl, thiopyranyl, 1,4-oxazinyl, morpholinyl, 1,4-thiazinyl, 1,3-thiazinyl, piperazinyl, benzimidazolyl, quinolyl, isoquinolyl, cinnolinyl, phthalazinyl, quinazolinyl, quinoxalinyl, indolinidyl Quinolizinyl, 1,8-naphthyridinyl, purinyl, pteridinyl, dibe Zofuraniru,
Carbazolyl, acridinyl, phenanthridinyl, phenazinyl, phenothiazinyl, phenoxazinyl and the like are used.

Examples of the cyclic hydrocarbon group include C _3-6 cycloalkyl such as cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl, 1-cyclopropenyl, 2-cyclobutenyl, 1-cyclohexenyl,
Cyclohexenyl, 1,3-cyclohexadiene-1-
C _3-6 cycloalkenyl such as yl, C _6-10 aryl such as phenyl and naphthyl and the like are used. (i) C _1-4 alkyl, such as methyl, ethyl, propyl,
Isopropyl, butyl, isobutyl, sec-butyl, tert-
Butyl is used. (ii) C _3-6 cycloalkyl such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl and the like are used. (iii) C _6-10 aryl such as phenyl, naphthyl and the like are used. (iv) C _1-4 alkoxy such as methoxy, ethoxy, propoxy, isopropoxy, butoxy, tert-butoxy and the like are used. (v) C _3-6 cycloalkyloxy such as cyclopropyloxy, cyclopentyloxy, cyclohexyloxy and the like are used. (vi) C _6-10 aryloxy such as phenoxy, naphthyloxy and the like are used. (vii) C _7-12 aralkyloxy such as benzyloxy, 2-phenethyloxy, 1-phenethyloxy and the like are used. (viii) C _1-4 alkylthio such as methylthio, ethylthio, propylthio, butylthio and the like are used. (ix) C _3-6 cycloalkylthio such as cyclopropylthio, cyclopentylthio, cyclohexylthio and the like are used.

(X) C _6-10 arylthio such as phenylthio, naphthylthio and the like are used. (xi) C _7-12 aralkylthio such as benzylthio, 2
-Phenethylthio, 1-phenethylthio and the like are used. (xii) mono C _1-4 alkylamino such as methylamino, ethylamino, propylamino, isopropylamino,
Butylamino, isobutylamino, tert-butylamino and the like are used. (xiii) di C _1-4 alkylamino such as dimethylamino, diethylamino, dipropylamino, dibutylamino,
N-methyl-N-ethylamino, N-methyl-N-propylamino, N-methyl-N-butylamino and the like are used. (xiv) C _3-6 cycloalkylamino such as cyclopropylamino, cyclopentylamino, cyclohexylamino and the like are used. (xv) C _6-10 arylamino such as anilino is used. (xvi) _C7-12 aralkylamino such as benzylamino, 2-phenethylamino, 1-phenethylamino and the like are used. (xvii) Halogen such as fluorine, chlorine, bromine, iodine is used. (xviii) C _1-4 alkoxycarbonyl such as methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, isopropoxycarbonyl, butoxycarbonyl, ter
t-butoxycarbonyl, isobutoxycarbonyl and the like are used. (xix) C _6-10 aryloxycarbonyl such as phenoxycarbonyl is used.

(Xx) C _3-6 cycloalkyloxycarbonyl, for example, cyclopropyloxycarbonyl, cyclopentyloxycarbonyl, cyclohexyloxycarbonyl and the like are used. (xxi) C _7-12 aralkyloxycarbonyl, for example, benzyloxycarbonyl, 1-phenethyloxycarbonyl, 2-phenethyloxycarbonyl and the like are used. (xxii) C _1-5 alkanoyl such as formyl, acetyl, propionyl, butyryl, pivaloyl and the like are used. (xxiii) C _1-15 alkanoyloxy such as formyloxy, acetoxy, butyryloxy, pivaloyloxy,
Pentanoyloxy, hexanoyloxy, heptanoyloxy, octanoyloxy, nonanoyloxy, decanoyloxy, undecanoyloxy, dodecanoyloxy, tridecanoyloxy, tetradecanoyloxy, pentadecanoyloxy, and the like are 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-benzylcarbamoyl and the like are used. (xxv) Carbamoyloxy having a substituent, for example, N-methylcarbamoyloxy, N, N-dimethylcarbamoyloxy, N-ethylcarbamoyloxy, N-benzylcarbamoyloxy, N, N-dibenzylcarbamoyloxy, N -Phenylcarbamoyloxy and the like are used. (xxvi) C _1-4 alkanoylamino such as formylamino, acetamide, propionamide, butyrylamide and the like are used. (xxvii) C _6-10 arylcarbonylamino such as benzamide is used. (xxviii) C _1-4 alkoxycarbonylamino such as methoxycarbonylamino, ethoxycarbonylamino,
Butoxycarbonylamino, tert-butoxycarbonylamino and the like are used. (xxix) C _7-12 aralkyloxycarbonylamino, for example, benzyloxycarbonylamino, 4-methoxybenzyloxycarbonylamino, 4-nitrobenzyloxycarbonylamino, 4-chlorobenzyloxycarbonylamino and the like are used.

(Xxx) Substituted sulfonylamino such as methanesulfonylamino, ethanesulfonylamino, butanesulfonylamino, benzenesulfonylamino, toluenesulfonylamino, naphthalenesulfonylamino, trifluoromethanesulfonylamino, 2-chloroethanesulfonylamino, 2,2, For example, 2-trifluoromethanesulfonylamino is used. (xxxi) 1 to 5 heterocyclic groups, nitrogen, oxygen and sulfur atoms
A cyclic group containing, for example, 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-oxazolyl, 3-, 4- or 5-isoxazolyl, 3-,
4- or 5-isothiazolyl, 2-, 4- or 5-thiazolyl, piperidinyl, 2-, 3- or 4-pyridyl,
Piperazinyl, pyrimidinyl, pyranyl, tetrahydropyranyl, tetrahydrofuryl, indolyl, quinolyl, 1,
3,4-oxadiazolyl, thieno [2,3-d] pyridyl,
1,2,3-thiadiazolyl, 1,3,4-thiadiazolyl,
1,2,3-triazolyl, 1,2,4-triazolyl, 1,
3,4-triazolyl, tetrazolyl, 4,5-dihydro-
1,3-Dioxolyl, tetrazolo [1,5-b] pyridazinyl, benzothiazolyl, benzoxazolyl, benzimidazolyl, benzothienyl and the like are used. (xxxii) Heterocyclic thio, heterocyclic oxy, heterocyclic amino or heterocyclic carbonylamino, and groups in which the above-mentioned heterocyclic group (xxxi) is bonded to a sulfur atom, an oxygen atom, a nitrogen atom or a carbonylamino group, respectively, are used. (xxxiii) di C _1-4 alkyl phosphinothioylamino,
For example, dimethylphosphinothioylamino, diethylphosphinothioylamino and the like are used. (xxxiv) alkoxyimino, for example, methoxyimino, ethoxyimino, 2-fluoroethoxyimino, carboxymethoxyimino, 1-carboxy-1-methylethoxyimino, 2,2,2-trichloroethyloxycarbonylmethoxyimino, 1- (2 , 2,2-trichloroethyloxycarbonyl) -1-methylethoxyimino, (2-aminothiazol-4-yl) methoxyimino, (1H-imidazol-4-yl) methoxyimino and the like. (xxxv) C _1-4 alkylsulfonyloxy such as methanesulfonyloxy, ethanesulfonyloxy, butanesulfonyloxy and the like are used. (xxxvi) C _6-10 arylsulfonyloxy such as benzenesulfonyloxy, toluenesulfonyloxy and the like are used. (xxxvii) Di-C _6-10 arylphosphinothioylamino such as diphenylphosphinothioylamino is used. (xxxviii) optionally substituted thiocarbamoylthio, for example, thiocarbamoylthio, N-methylthiocarbamoylthio, N, N-dimethylthiocarbamoylthio, N-ethylthiocarbamoylthio, N-benzylthiocarbamoylthio, N , N-dibenzylthiocarbamoylthio, N-phenylthiocarbamoylthio and the like. (xxxix) Silyloxy, for example, trimethylsilyloxy, t-butyldimethylsilyloxy, t-butyldiphenylsilyloxy, dimethylphenylsilyloxy and the like are used.

(XL) silyl, for example, trimethylsilyl, t
-Butyldimethylsilyl, t-butyldiphenylsilyl,
Dimethylphenylsilyl and the like are used. (xLi) C _1-4 alkylsulfinyl such as methylsulfinyl, ethylsulfinyl, propylsulfinyl,
Butylsulfinyl and the like are used. (xLii) C _6-10 arylsulfinyl such as phenylsulfinyl, naphthylsulfinyl and the like are used. (xLiii) C _1-4 alkylsulfonyl such as methanesulfonyl, ethanesulfonyl, butanesulfonyl and the like are used. (xLiv) C _6-10 arylsulfonyl such as benzenesulfonyl, toluenesulfonyl and the like are used. (xLv) C _1-4 alkoxycarbonyloxy such as methoxycarbonyloxy, ethoxycarbonyloxy, tert
-Butoxycarbonyloxy and the like are used. (xLvi) C _1-4 haloalkyl such as trifluoromethyl, 1,1,2,2-tetrafluoroethyl, difluoromethyl, monofluoromethyl, trichloromethyl, dichloromethyl, monochloromethyl and the like are used. (XLVII) C _1-4 haloalkyloxy, C _1-4 haloalkylthio, C _1-4 haloalkylsulfinyl or C _1-4 haloalkylsulfonyl, such as the above-mentioned C _1-4 haloalkyl
A group in which (xLvi) is bonded to an oxygen atom, a sulfur atom, a sulfinyl group or a sulfonyl group, or the like is used. (xLviii) cyano group, nitro group, hydroxyl group, carboxyl group, sulfonic acid group and phosphonic acid group. (xLix) C _1-4 alkyloxysulfonyl such as methoxysulfonyl, ethoxysulfonyl, butoxysulfonyl and the like are used.

(L) C _6-10 aryloxysulfonyl,
For example, phenoxysulfonyl, tolyloxysulfonyl and the like are used. (Li) C _7-12 aralkyloxysulfonyl, for example, benzyloxysulfonyl, 2-phenethyloxysulfonyl, 1-phenethyloxysulfonyl and the like are used. (Lii) Di-C _1-4 alkyloxyphosphoryl, for example, dimethoxyphosphoryl, diethoxyphosphoryl, dibutoxyphosphoryl and the like are used.

Preferred examples of the α-unsaturated amines represented by the formula [1] or salts thereof include, for example,

Embedded image Wherein R ^1a is a mono-C _1-6 alkylamino group, N—C
_1-6 alkyl-N-formylamino group or amino group,
R ^2a represents a C _1-4 alkyl group or a C _1-4 alkoxy group,
^a represents a chloropyridyl group], an α-unsaturated amine represented by the formula:

Embedded image [Wherein R ^1b is a mono-C _1-6 alkylamino group or N-
Wherein A ^a is as defined above, or a salt thereof, a C _1-6 alkyl-N-formylamino group,

Embedded image Wherein, R ^1c is a di -C _1-6 alkylamino group, R ^2b is a hydrogen atom, a formyl or C _1-4 alkyl group, A ^b represents a pyridyl or chloropyridyl radical represented by α-
Unsaturated amines or salts thereof, formula

Embedded image [The symbols in the formula have the same meanings as described above], and α-unsaturated amines or salts thereof.

[0017] The above ^{[1 a], [1 b} ], in [1 ^c], R ^1a and R
^The mono-C _1-6 alkylamino group represented by ^1b is, for example, monomethylamino, monoethylamino, mono-n-propylamino, mono-i-propylamino, mono-n-butylamino, mono-i-butylamino , Mono-n-hexylamino and the like, and preferably mono-C _1-4 alkylamino such as monomethylamino and monoethylamino. ^NC _1-6 alkyl-N- represented by R ^1a and R ^1b
Formylamino groups include, for example, N-methyl-N-formylamino, N-ethyl-N-formylamino, N-n-propyl-N-formylamino, Ni-propyl-N-formylamino, N-n- Butyl-N-formylamino, N
-N-hexyl-N-formylamino and the like, preferably N-C _1-4 alkyl-N such as N-methyl-N-formylamino, N-ethyl-N-formylamino and the like.
-Formylamino and the like. Di-C _{1-6 represented} by R ^1c
Alkylamino groups include, for example, dimethylamino, N-ethyl-N-methylamino, diethylamino, di-n-propylamino, di-i-propylamino, di-n-butylamino, di-i-butylamino, di- n-pentylamino, di-i
- pentylamino, a di -n- hexylamino, etc., preferably such as dimethylamino, N- ethyl -N- methylamino, di -C _1-4 alkylamino such as diethylamino or the like. The C _1-4 alkyl group represented by R ^2a and R ^2c is, for example, those described above for R ² , and is preferably, for example, methyl, ethyl and the like. C represented by R ^2a
_{The 1-4} alkoxy group is, for example, those described above for R ² , and is preferably methoxy, ethoxy, or the like. Chloropyridyl group represented by A ^a and A ^b are, 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;
-Chloro-3-pyridyl and the like. Pyridyl represented by A ^b includes 3-pyridyl, 4-pyridyl, preferably 3-pyridyl.

Representative α-unsaturated amines of the formula [1] or salts thereof include, for example,

Embedded image [Wherein X ^2a represents a hydrogen atom, C _1-4 alkoxycarbonyl or C _1-4 alkylsulfonylthiocarbamoyl,
^2c is a hydrogen atom, C _1-3 acyl, C _1-4 alkyl, mono- or di-C _1-4 alkoxy-C _1-4 alkyl, C _7-9 aralkyl, mono- or di-C _1-4 alkyl Amino or C _1-4 alkoxy, and ^Ac is optionally substituted with a halogen atom, C _1-4 alkyl or C _1-4 alkoxy.
Or 4-pyridyl, pyrazinyl or 4- or 5-
R ^6a and R ^7a each represent hydrogen, a lower alkyl group, a halogenated lower alkyl group or a C _1-4 acyl group, and n has the same meaning as described above. Α-
Unsaturated amines or salts thereof, formula

Embedded image [Wherein X ^2a represents a hydrogen atom, C _1-4 alkoxycarbonyl or C _1-4 alkylsulfonylthiocarbamoyl,
^1d is amino, mono- or di-C _1-4 alkylamino,
N—C _1-4 alkyl-NC _1-3 acylamino, C _7-9 aralkylamino, halogenothiazolyl-C _1-2 alkylamino or C _1-4 alkoxy-C _1-2 alkylamino is represented by R ^2c is a hydrogen atom, C _1-3 acyl, C _1-4 alkyl, mono- or di-C _1-4 alkoxy-C _1-4 alkyl, C
_7-9 aralkyl, mono- - or di -C _1-4 alkylamino or C _1-4 alkoxy, n a is 0, 1 or 2, A ^d
Represents 3- or 4-pyridyl, pyrazinyl or 5-thiazolyl which may be substituted with a halogen atom, C _1-4 alkyl or C _1-4 alkoxy. Α
-Unsaturated amines or salts thereof,

Embedded image [Wherein, X ^2b represents a hydrogen atom or C _1-2 alkylsulfonylthiocarbamoyl, R ^1e represents amino, mono- or di-
C _1-2 alkylamino or N-C _1-2 alkyl-N-formylamino, R ^2d is a hydrogen atom, C _1-2 alkyl or C _1-3 acyl, A ^e is a group represented by the formula

Embedded image (Hal represents a halogen atom). ]
An α-unsaturated amine represented by the formula or a salt thereof,

Embedded image [Wherein, X ^2c represents a hydrogen atom or methylsulfonylthiocarbamoyl, R ^1f represents amino, methylamino, dimethylamino or N-methyl-N-formylamino, R ^2d
Is a hydrogen atom, formyl or C _1-2 alkyl, and A ^e is a formula

Embedded image [Hal represents a halogen atom]. ]
An α-unsaturated amine represented by the formula or a salt thereof,

Embedded image Wherein R ^1e is amino, mono- or di-C _1-2 alkylamino or NC _1-2 alkyl-N-formylamino, R ^2e is C _1-2 alkyl or formyl, and Hal is halogen Indicates an atom. Α-unsaturated amines or salts thereof.

The above equation [1]^e] ~ [1ⁱ], X^2a, X^2bAnd X
^2cA group represented by R^1d, R^1eAnd R ^1fA group represented by R
^2c, R^2dAnd R^2eA group represented by A^c, A^dAnd A^eIndicated by
Group, R^6aA group represented by R^7aThe group represented by
X above each^Two, R¹, R^Two, A, R⁶, R⁷Etc. described in
Is used. A compound represented by the general formula [1] or
The salt can be produced by a similar known method.
And a method described in Japanese Patent Application No. 63-192383.
It can also be made. When compound [1] is obtained in free form
In this case, the salt may be formed using a conventional method,
In addition, the product obtained as a salt was converted into the free form using a conventional method.
May be. Compound [1] is X¹, X^Two, R¹, R^TwoAnd A
Acidity such as carboxyl group, sulfo group, phosphono group
When it has a group, it may form a salt with a base,
Such bases include, for example, sodium, potassium, lithium
Inorganic salts such as calcium, magnesium, and ammonia
Groups such as pyridine, collidine, triethylamine, tri
An organic base such as ethanolamine is used. Ma
X¹, X^Two, R¹, R^TwoAmino group and substituted amino
Forms an acid addition salt when it has a basic group such as
Such acid addition salts include hydrochloride, bromide
Hydrochloride, hydroiodide, nitrate, sulfate, phosphate, vinegar
Acid salt, benzoate, maleate, fumarate, succinic acid
Salt, tartrate, citrate, oxalate, glyoxylic acid
Salt, aspartate, methanesulfonate, methanedis
Sulfonate, 1,2-ethanedisulfonate, benzenes
A sulfonate or the like is used.

Representative compounds of the α-unsaturated amines of the formula [I] used in the active substance combinations according to the invention include 1- [N- (6-chloro-3-pyridylmethyl)- N-methyl] amino-1-methylamino-2-nitroethylene, 1- (6-chloro-3-pyridylmethyl) amino-1-dimethylamino-2-nitroethylene, 1- [N- (6-chloro- 3-pyridylmethyl)-
N-ethyl] amino-1-methylamino-2-nitroethylene, 1- [N- (6-chloro-3-pyridylmethyl) -N-methyl] amino-1-dimethylamino-2-
Nitroethylene, 1- [N- (6-chloro-3-pyridylmethyl) -N-ethyl] amino-1- (N-formyl-N-methyl) -2-nitroethylene, 1- [N- (2
-Chloro-5-thiazolylmethyl) -N-ethyl] amino-1-methylamino-2-nitroethylene, 1- [N
-(2-chloro-5-thiazolylmethyl)] amino-1
-Dimethylamino-2-nitroethylene, 1- [N-
(6-Bromo-3-pyridylmethyl) -N-methyl] amino-1-methylamino-2-nitroethylene, 1-
[N- (6-chloro-3-pyridylmethyl) -N-formyl] amino-1-dimethylamino-2-nitroethylene, 1- [N- (6-fluoro-3-pyridylmethyl)
-N-methyl] amino-1-methylamino-2-nitroethylene, 1- [N-ethyl-N- (6-fluoro-3
-Pyridylmethyl)] amino-1-methylamino-2-
Nitroethylene, 1- [N- (6-bromo-3-pyridylmethyl) -N-ethyl] amino-1-methylamino-
2-nitroethylene, 1- [N- (2-chloro-5-thiazolylmethyl) -N-methyl] amino-1- (N-formyl-N-methyl) amino-2-nitroethylene,
-[N- (2-chloro-5-thiazolylmethyl) -N-
Ethyl] amino-1- (N-formyl-N-methyl) amino-2-nitroethylene, 1- [N- (6-bromo-
3-pyridylmethyl) -N-methyl] amino-1- (N
-Formyl-N-methyl) amino-2-nitroethylene, 1- [N- (6-bromo-3-pyridylmethyl)-
N-ethyl] amino-1- (N-formyl-N-methyl) amino-2-nitroethylene, 1- [N- (6-bromo-3-pyridylmethyl) -N-formyl] amino-
1-dimethylamino-2-nitroethylene, 1- [N-
(6-Chloro-3-pyridylmethyl) -N- (2,2,
2-trifluoroethyl)] amino-1-methylamino-2-nitroethylene, 1- [N- (2-chloro-5-
Thiazolylmethyl) -N-formyl] amino-1-dimethylamino-2-nitroethylene, 1- (6-chloro-
3-pyridylmethyl) amino-1-methylamino-2-
Nitroethylene, 1-amino-1- [N- (6-chloro-3-pyridylmethyl) -N-methyl] amino-2-nitroethylene and the like.

The above-mentioned α-unsaturated amines or salts thereof and their use as insecticides are described by the present inventors in Japanese Patent Application No. 63-192383. In addition, one of the fungicides used in the active substance combination according to the present invention includes the following compounds. (2) (Z) -2′-methylacetophenone-4,6-
Dimethylpyrimidin-2-ylhydrazone (ferimzone), 4,5,6,7-tetrachlorophthalide (fusalide), 3-alkyloxy-1,2-benzisothiazole-1,1-dioxide (probenazole), diisopropyl -1,3-dithiolan-2-ylidene-malonate (isoprothiolane), kasugamycin hydrochloride (kasugamycin), O-ethyl-S, S-diphenyldithiophosphate (edifenphos), O, O-diisopropyl-S-benzylthiophosphate ( Iprobenphos), 5-methyl-1,2,4-triazolo [3,
4-b] benzothiazole (tricyclazole), validamycin A (validamycin), α, α, α-trifluoro-3-isopropoxy-O-trianilide (flutranyl), 3′-isopropoxy-2-methylbenzanilide (mepronil) ), 1- (4-chlorobenzyl)
-1-cyclopentyl-3-phenylurea (pencyclone) and the like.

The above-mentioned fungicides, which are one component of the active substance combination according to the present invention, are already known and described, for example, in the above-mentioned Pasteyside Manual. Next, the weight ratio of the active compounds of each group in the active substance combinations according to the invention is generally based on 1 part by weight of the active compounds of the active compound group of α-unsaturated amines of the formula [1] or salts thereof. (2)
Active compounds of the active compound group of known fungicides of 0.1 to 100
The active compound combinations according to the invention, which can be used in parts by weight, preferably 0.5 to 50 parts by weight, exhibit excellent insecticidal fungicidal activity, foliar application, water or water application, irrigation on the soil surface, soil admixture, or seedling raising It can be used by box processing and the like. The active substance combinations according to the invention exhibit a strong insecticidal fungicidal activity at lower doses than when each active substance is applied alone, so that phytotoxicity to crops can be completely avoided and in conventional insecticides or fungicides, Immediate effect,
Lack of balance of residual effect, systemic transfer, etc., and problems with insecticidal or bactericidal effects, such as toxicity to warm-blooded animals and fish, safety to useful insects and natural enemies, and phytotoxicity to crops. It can be used even in situations where the use is restricted due to the fact.

The insecticidal / bactericidal composition of the present invention can control the following pests (diseases and pests). For example, among insects, in particular, Hemiptera pests (Nephotettix cincticeps), planthoppers (Nilaparvata lugens), and staghorn planthoppers (Soga)
tella furucifera, brown groundhopper (Laodephax stri)
atellus) and other insects of the order Lepidoptera, Chilo sup
pressalis), Cleoptera (Cnaphalocrocis medinali)
s), Naranga aenescens and the like, and the insect weevil, Lissorhoptrus oryzaph
ilus), rice weevil (Echinocnemus squameus), rice dung beetle (Oulema oryzae), etc., and Plutella macli which is an insect of the order Lepidoptera of garden crops such as fruit trees, vegetables and tea.
pennis), white butterfly (Pieris brassicae), armyworm (Mamestra brassicae), and anemone
(Adoxophyes sp.), Canohosoga (Caloptilia theivor)
a) Aphids such as aphids (Myzus persicae) and cotton aphids (Aphis go)
ssyipii), apple aphids (Aphis poni), etc., and scale insects (Unaspis yanoensi
s), Pseudodococcus comstock
i) etc.), whiteflies (Trialeurodes vaporari)
orum), Leafhopper (Empoasca onuki)
i) etc., Thrips palmiflora (Scirtothrips dorsalis), Thrips palmi (Thrips palmi), etc., which are pests of the order Thysanoptera;
And the like. Examples of the phytopathogenic fungi include archaebacteria (Archimiseites), algae (Phycomycetes), ascomycetes (Ascomycetes), basidiomycetes (Basidiomicetes), and incomplete bacteria (Fungi lmperfecti).
As a representative example of the sterilization spectrum of the above plant diseases,
For example, rice blast (Pyricularia oryzae), rice sheath blight (Pellicularia sasakii), and Rhizoctionia solani (Rhizoctionia sol) which is a kind of pathogen of vegetable seedling blight.
ani) and the like.

The active compound combinations according to the invention each have the formula
[1] α-unsaturated amines or salts thereof and (2) above
It can be in the form of a mixed preparation that can be taken by a general agricultural chemical containing both the bactericide components of, for example, emulsions, wettable powders, powders, granules, tablets, sprays and the like. Α
-An unsaturated amine or a salt thereof and the bactericide component of the above (2) can be made into a usual formulation form, for example, an emulsion, a wettable powder or the like. These preparations have α of the above formula [1].
-Dissolving or dispersing the unsaturated amines or salts thereof or the active ingredient of the above (2) singly or in a suitable liquid carrier, or mixing or adsorbing with a suitable solid carrier; It can be produced by a known method by adding an emulsifier, a suspending agent, a spreading agent, a penetrant, a wetting agent, a mucilage, a stabilizer and the like. Although the content ratio of all the active ingredients in the preparation varies depending on the purpose of use, emulsions, wettable powders and the like are 5-70.
About 10% by weight is appropriate as a powder.
Is appropriate, and 0.5 to 10% by weight is appropriate as a granule, but these concentrations may be appropriately changed depending on the purpose of use. When used, the emulsion, wettable powder and the like are appropriately diluted and increased (for example, 100 to 10,000 times) with water or the like and sprayed. Examples of the liquid carrier (solvent) used include water, alcohols (eg, methyl alcohol, ethyl alcohol,
n-propyl alcohol, isopropyl alcohol, ethylene glycol, etc.), ketones (for example, acetone,
Methyl ether, etc.), ethers (eg, dioxane, tetrahydrofuran, ethylene glycol monomethyl ether, propylene glycol monomethyl ether, etc.), aliphatic hydrocarbons (eg, kerosene, kerosene,
Fuel oil, etc.), aromatic hydrocarbons (eg, benzene, toluene, xylene, solvent naphtha, methylnaphthalene, etc.), halogenated hydrocarbons (eg, dichloromethane, chloroform, carbon tetrachloride, etc.), acid amides (eg, , Dimethylformamide, dimethylacetamide, etc.), esters (eg, ethyl acetate, butyl acetate,
Fatty acid glycerin esters, etc.), nitriles (for example,
Solvents such as acetonitrile, propionitrile, etc.) are suitable, and these can be used alone or as a mixture of two or more at an appropriate ratio.

Examples of the solid carrier (diluting / extending agent) include vegetable powders (eg, lactose, soybean powder, tobacco powder, flour, wood powder, etc.) and mineral powders (eg, kaolin, bentonite, acid clay, etc.). , Talc, silica such as mica powder, etc.), diatomaceous earth, calcium carbonate, alumina, sulfur powder, activated carbon, etc., and one or more of these can be mixed and used in an appropriate ratio. Surfactants used as emulsifiers, spreading agents, penetrants, dispersants and the like include soaps and polyoxyethylene alkyl allyl ethers [for example, Neugen EA (EA) 142; Nonal; manufactured by Daiichi Kogyo Seiyaku Co., Ltd .; manufactured by Toho Chemical Co., Ltd.], alkyl sulfates (eg, Emal 10, Emal 40; manufactured by Kao Corporation), alkyl sulfonates [eg, Neogen, Neogen T; Manufactured by Daiichi Kogyo Seiyaku Co., Ltd., Neoperex; manufactured by Kao Corporation], polyethylene glycol ethers [for example, Nonipol 8
5. Nonionic and anionic surfactants such as 5, Nonipol 100, Nonipol 160; manufactured by Sanyo Chemical Co., Ltd.] and polyhydric alcohol esters [for example, Tween 20, Tween 80; manufactured by Kao Corporation] are appropriately used. Can be The active compound combinations of the invention are useful in their commercially useful formulations and in the use forms prepared by these formulations.
It can also be used as a mixture with other active compounds, for example insecticides, fungicides, acaricides, nematicides, fungicides, growth regulators. The insecticidal fungicidal composition of the present invention thus obtained is extremely safe, and has excellent toxicity. And the insecticidal and bactericidal composition of the present invention is a conventional insecticide,
It can be used in the same manner as a bactericide, and as a result, it can exhibit superior effects as compared with conventional products. For example, the insecticidal / bactericidal composition of the present invention can be used for a target pest by, for example, treatment of a nursery box, spraying of foliage of crops, spraying of insects, application to paddy water in water, or soil treatment. The amount of application can be varied over a wide range according to the time of application, the place of application, the method of application, and the like. In general, the active ingredient (α-unsaturated amines of formula [1] or a salt thereof) per hectare And known fungicides) 0.3g-3000g
It is desirable that the application is preferably 50 g to 1000 g. When the insecticidal / bactericidal composition of the present invention is a wettable powder, it may be diluted and used so that the final concentration of the active ingredient is in the range of 0.1 to 1000 ppm, preferably 10 to 500 ppm.

[0026]

DESCRIPTION OF THE PREFERRED EMBODIMENTS Next, the contents of the present invention will be specifically described with reference to examples, but the present invention should not be limited to these. [Examples] Example 1 Test for controlling insecticide against brown planthopper and rice blast by spraying foliage of liquid solution 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; Kao Corporation) 2.0 parts by weight An active compound mixture or 1.0 part by weight of the active compound alone described in the column of the reagent in Table 1 below is mixed with the solvent containing the emulsifier, The mixture is used as a spreading agent (Dyne
^TM (TM indicates a trade name.)) Diluted to a predetermined concentration with 3,000-fold tap water.

Test on brown planthopper (spray test) Test method: To a rice plant of about 30 cm in height (20 days after transplanting) planted in a vinyl chloride pot having a diameter of about 11.3 cm, 20 larvae of the 3rd to 4th larvae of brown planthopper are directed to each pot. Inoculated diameter 11
cm, a cylinder made of transparent PVC film (height: 67cm) (top opening covered with ghosts)
The next day, a water diluent of the above-mentioned active compound having a predetermined concentration prepared in advance was sprayed from an opening of 20 ml per pot using a spray gun and placed in a glass thermostat at 25 ± 1 ° C., and the number of surviving insects two days later was counted. The insecticidal rate [= {(number of test animals−number of surviving insects) / number of test animals} × 100] was determined. The test was performed in a two-part system. Test method for controlling blast on rice (spray test) Test method: A water dilution of a predetermined concentration of the above active compound was sprayed on a rice plant 32 days after sowing planted in a vinyl chloride pot having a diameter of about 9.0 cm using a spray gun. Spray in a spray chamber. One day later, the rice blast pathogenic spores are naturally infected from the rice blast-affected leaves, and kept at room temperature of 25 ± 2 ° C. and 100% relative humidity for 2 days at room temperature. ° C
After 5 days, the disease rate was classified by examining the lesion area ratio (%) per plant, and the control value (%) was determined by the following formula. The test was performed in a two-part system. Degree of morbidity Lesion area percentage (%) 00 Less than 0.52 1 Less than 2 to 5 Less than 5 to 10 3 Less than 10 to 20 4 Less than 20 to 40 5 More than 40 Control value (%) = {( (Disease degree-Disease degree of treated section) / (Disease degree of untreated section)} × 100 The results are shown below.

[0028]

[Table 1]

Notes: 1. Compound of formula [1] used in this test: Compound No. 1: 1- [N- (6-chloro-3-pyridylmethyl) -N-methyl] amino-1-methylamino-2
-Nitroethylene Compound No. 2: 1- [N- (6-chloro-3-pyridylmethyl) -N-ethyl] amino-1- (N-formyl-
N-methyl) -2-nitroethylene compound No. 3: 1- [N- (6-chloro-3-pyridylmethyl) -N-ethyl] amino-1-methylamino-2
-Nitroethylene compound No. 4: 1- [N- (2-chloro-5-thiazolylmethyl)] amino-1-dimethylamino-2-nitroethylene compound No. 5: 1- [N- (2-chloro-5) -Thiazolylmethyl) -N-formyl] amino-1-dimethylamino-2-nitroethylene 2. Known compounds used in this test: Compound (A): Ferimzone Compound (B): Tricyclazole Compound (C): Kasugamycin

Example 2 Effect of Controlling Granules on Nursing Box Treatment of Rice Planthopper and Rice Blast Preparation of Reagents: 6 parts by weight of the active compound mixture described in the column of Reagents in Table 2 below Alternatively, 89 parts by weight to 93 parts by weight of clay is added to 2 (or 4) parts by weight of the active compound alone and 5 parts by weight of sodium ligninsulfonate to make the total amount 100 parts by weight, and the mixture is ground and mixed, and a small amount of water is added. After well kneading, the mixture was extruded, granulated and dried to produce granules. Test method: 50 g of each of the above granules was sprayed on rice seedlings 3 weeks after sowing planted in a rice seedling box, and the diameter was about 1 day the next day.
It was transplanted into a 1.3 cm vinyl chloride pot and left in a glass greenhouse at 25 ± 1 ° C. Three weeks after transplantation, 20 chicks per pot were inoculated with larvae of the brown planthopper, male and female, at a ratio of 1: 1.
Cover with a cylinder made of transparent vinyl chloride film (11 cm, height 67 cm) (top opening covered with ghosts), check the number of surviving insects two days later, and determine the insecticidal rate [= {(number of test animals −
(Number of surviving insects) / number of test animals} × 100]. Rice after the insecticidal test (24 days after transplantation, the rice blast pathogen is naturally infected from the rice blast-infected leaves and kept at an inoculation room temperature of 25 ± 2 ° C. and 100% relative humidity for 2 days, then the temperature is 25 ± 2 ° C.
After 5 days, the disease rate was classified by examining the lesion area ratio (%) per plant, and the control value (%) was obtained by the following formula. The test was performed in a two-part system. Degree of morbidity Lesion area percentage (%) 00 Less than 0.52 1 Less than 2 to 5 Less than 5 to 10 3 Less than 10 to 20 4 Less than 20 to 40 5 More than 40 Control value (%) = {( Morbidity-morbidity of treated group / (morbidity of untreated group)} × 100 The results are summarized below.

[0031]

[Table 2]

Note) 1. Compound of formula [1] used in this test: Compound No. 1: 1- [N- (6-chloro-3-pyridylmethyl) -N-methyl] amino-1-methylamino-2
-Nitroethylene Compound No. 2: 1- [N- (6-chloro-3-pyridylmethyl) -N-ethyl] amino-1- (N-formyl-
N-methyl) -2-nitroethylene compound No. 3: 1- [N- (6-chloro-3-pyridylmethyl) -N-ethyl] amino-1-methylamino-2
-Nitroethylene compound No. 4: 1- [N- (2-chloro-5-thiazolylmethyl)] amino-1-dimethylamino-2-nitroethylene compound No. 5: 1- [N- (2-chloro-5) -Thiazolylmethyl) -N-formyl] amino-1-dimethylamino-2-nitroethylene 2. Known fungicides used in this test: Compound (A): Tricyclazole Compound (B): Probenazole

Example 3 Test of control effect on brown planthopper and rice sheath blight by spraying rice foliage with liquid solution 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 1.0 part by weight of the active compound mixture or the active compound alone described in the column of the reagent agent in Table 3 below. It is mixed with a solvent containing an emulsifier and the mixture is used as a spreading agent (Dyne ^™ )
The solution was diluted with tap water for doubling to a predetermined concentration. Test on brown planthopper Test method: Rice plant of about 30 cm in height (20 days after transplanting) planted in a vinyl chloride pot of about 11.3 cm in diameter was inoculated with 20 larvae of 3 to 4th larvae of brown planthopper per pot to a diameter of 11
cm, a cylinder made of transparent PVC film with a height of 67 cm (the top opening is covered with ghosts),
The following day, a water diluent of the above-mentioned active compound having a predetermined concentration prepared in advance was sprayed from the opening portion of each pot using a spray gun, and placed in a glass thermostat at 25 ± 1 ° C., and the number of surviving insects after 2 days was examined. And the insecticidal rate [= {(number of test animals−number of live insects) / number of test animals} × 100] were determined. The test was performed in a two-part system. Control effect test on rice sheath blight A potion of a water dilution of a predetermined concentration of the above-mentioned active compound prepared in advance in rice at the panicle formation stage cultivated in a 1 / 5000a vinyl chloride pot in a flooded state using a spray gun. Per day, and inoculate the test rice plant on the day after the spraying with the sheath blight fungus cultured on a potato agar medium for 2 days at a temperature of 28 to 30 ° C. and a relative humidity of 95% or more. After leaving for 10 days to cause the sheath blight, the degree of the disease was investigated, and the control value {= (100-damage)} was determined by the following formula. The test was performed in two consecutive sessions. Damage = {(3n ₃ + 2n ₂ + n ₁ + n ₀ ) / 3N} × 10
0, where N: total number of stems examined n ₀ : number of disease-free stems n ₁ : number of stems affected up to the lower first leaf leaf sheath. n ₂ : the number of stems affected up to the lower second leaf leaf sheath. n ₃ : number of stems affected to the lower third leaf position or higher. The results are summarized below.

[0034]

[Table 3]

Note) 1. Compound of general formula [1] used in this test: Compound No. 1: 1- [N- (6-chloro-3-pyridylmethyl) -N-methyl] amino-1-methylamino-2
-Nitroethylene Compound No. 2: 1- [N- (6-chloro-3-pyridylmethyl) -N-ethyl] amino-1- (N-formyl-
N-methyl) -2-nitroethylene compound No. 3: 1- [N- (6-chloro-3-pyridylmethyl) -N-ethyl] amino-1-methylamino-2
-Nitroethylene compound No. 4: 1- [N- (2-chloro-5-thiazolylmethyl)] amino-1-dimethylamino-2-nitroethylene compound No. 5: 1- [N- (2-chloro-5) -Thiazolylmethyl) -N-formyl] amino-1-dimethylamino-2-nitroethylene 2. Known fungicides used in this test: Compound (A): Validamycin A Compound (B): Flutolanil

According to Tables 1, 2 and 3, the insecticidal fungicidal composition of the present invention is more cooperative with brown planthopper, brown planthopper, rice blast and rice sheath blight as compared with the use of each active ingredient alone. It is proved to have excellent insecticidal and bactericidal action and fast-acting and afterglow properties.

Example 4 (Wettable powder) Compound No. 1 (5% by weight), compound (A) (20% by weight), sodium ligninsulfonate (5% by weight) shown in Example 1, Oxyethylene glycol ether (Nonipol 85 ^™ : 5% by weight), white carbon (10% by weight) and clay for wettable powder (55% by weight) were mixed well to produce a wettable powder.

Example 5 (Wettable powder) Compound No. 3 (5% by weight), compound (A) (15% by weight) shown in Example 3, polyoxyethylene glycol ether (Nonipol 85 ^™ : 5% by weight) %), White carbon (10% by weight), clay for wettable powder (60% by weight)
Was mixed well to produce a wettable powder.

Example 6 (Powder) Compound No. 1 (0.25% by weight), compound (A) (2.0% by weight), white carbon (5.0% by weight), clay (92.75% by weight) shown in Example 1 Was mixed well to produce a powder.

Example 7 (Powder) Compound No. 3 (0.25% by weight), Compound (A) (0.3% by weight), white carbon (5.0% by weight), clay (94.45% by weight) shown in Example 3 Was mixed well to produce a powder.

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[Procedure amendment]

[Submission date] July 1, 1998

[Procedure amendment 1]

[Document name to be amended] Statement

[Correction target item name] Claims

[Correction method] Change

[Correction contents]

[Claims]

1. A 1- [N- (6- chloro-3-pyridylmethyl) -N- ethyl] amino-1-methylamino-2-
An agricultural and horticultural insecticidal fungicidal composition comprising nitroethylene or a salt thereof, and 4,5,6,7-tetrachlorophthalide.

──────────────────────────────────────────────────続 き Continued on the front page (51) Int.Cl. ⁶ Identification code FI A01N 43:78) (A01N 43/78 43:54) (A01N 43/78 37:08) (A01N 43/78 43:16) (A01N 43/78 33:08) (A01N 43/80 43:78) (A01N 57/14 47:30)

Claims (12)

[Claims] (1) 1- [N- (6-chloro-3-pyridylmethyl) -N-ethyl] amino-1-methylamino-2-
Nitroethylene or a salt thereof, and (Z) -2′-methylacetophenone-4,6-gemethylpyrimidine-2-
An agricultural and horticultural insecticidal fungicidal composition containing ilhydrazone. 2. 1- [N- (6-chloro-3-pyridylmethyl) -N-ethyl] amino-1-methylamino-2-
An agricultural and horticultural insecticidal fungicidal composition comprising nitroethylene or a salt thereof, and 4,5,6,7-tetrachlorophthalide. (3) 1- [N- (6-chloro-3-pyridylmethyl) -N-ethyl] amino-1-methylamino-2-
Nitroethylene or a salt thereof, and 3-alkyloxy-
An agricultural and horticultural insecticidal fungicidal composition comprising 1,2-benzoisothiazole-1,1-dioxide. (4) 1- [N- (6-chloro-3-pyridylmethyl) -N-ethyl] amino-1-methylamino-2-
Nitroethylene or a salt thereof and diisopropyl-1,
An agricultural and horticultural insecticidal fungicidal composition comprising 3-dithiolan-2-ylidene-malonate. 5. 1- [N- (6-chloro-3-pyridylmethyl) -N-ethyl] amino-1-methylamino-2-
An agricultural and horticultural insecticidal fungicidal composition comprising nitroethylene or a salt thereof and kasugamycin hydrochloride. 6. A 1- [N- (6-chloro-3-pyridylmethyl) -N-ethyl] amino-1-methylamino-2- compound.
Nitroethylene or a salt thereof, and O-ethyl-S, S-
An agricultural and horticultural insecticidal fungicidal composition containing diphenyldithiophosphate. 7. A 1- [N- (6-chloro-3-pyridylmethyl) -N-ethyl] amino-1-methylamino-2- compound.
An agricultural and horticultural insecticidal fungicidal composition containing nitroethylene or a salt thereof, and O, O-diisopropyl-S-benzylthiophosphate. 8. A 1- [N- (6-chloro-3-pyridylmethyl) -N-ethyl] amino-1-methylamino-2- compound.
Nitroethylene or a salt thereof, and 5-methyl-1,2,2,
An agricultural and horticultural insecticidal fungicidal composition containing 4-triazolo [3,4-d] benzothiazole. 9. A 1- [N- (6-chloro-3-pyridylmethyl) -N-ethyl] amino-1-methylamino-2- compound.
An agricultural and horticultural insecticidal fungicidal composition containing nitroethylene or a salt thereof and validamycin A. 10. A 1- [N- (6-chloro-3-pyridylmethyl) -N-ethyl] amino-1-methylamino-2 compound.
An agricultural and horticultural insecticidal fungicidal composition comprising nitroethylene or a salt thereof and α, α, α-trifluoro-3′-isopropoxy-O-toluanilide. (11) 1- [N- (6-chloro-3-pyridylmethyl) -N-ethyl] amino-1-methylamino-2
-An agricultural and horticultural insecticidal fungicidal composition containing nitroethylene or a salt thereof and 3'-isopropoxy-2-methylbenzanilide. 12. 1- [N- (6-chloro-3-pyridylmethyl) -N-ethyl] amino-1-methylamino-2
-An agricultural and horticultural insecticidal fungicidal composition containing nitroethylene or a salt thereof and 1- (4-chlorobenzyl) -1-cyclopentyl-3-phenylurea.