JPS61243078A - Pyridazinone derivative, production thereof, and insecticidal, miticidal, nematocidal and fungicidal agent - Google Patents

Abstract

NEW MATERIAL:The compound of formula I [R is H or 1-6C alkyl; R<1> and R<2> are H, alkyl or haloalkyl; X is O or S; A is halogen or 1-6C alkyl; B is group of formula II, -CR<3>R<4>O-CR<3>R<4>-(R<3> and R<4> are H or 1-4C alkyl); m is 0 or 1; Q is (substituted) heterocyclic group containing 1-3 hetero-atoms and bonded via C atom, etc.]. EXAMPLE:2-t-Butyl-5-(5-t-butyl-2-thienylmethylthio)-4-methyl-3-(2-H)-p yridazinone. USE:Insecticidal, miticidal, nematocidal and fungicidal agent for agricultural and horticultural use, and repellent for mite parasitic to animal. PREPARATION:The compound of formula I can be produced by reacting the compound of formula III (X' is halogen, SH or OH) with the compound of formula IV (X'' is SH or OH when X' is halogen, and is halogen when X' is SH or OH) in a solvent, preferably in the presence of a base.

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention provides novel 5t2[(1-pyridazinone derivatives,
The present invention relates to a method for producing the same, as well as agricultural and horticultural insecticides, medicicides, nematocides, fungicides, and animal-friendly acaricides containing the derivative as an active ingredient. More details.

General formula [l]: [In the formula, R is a hydrogen atom or a linear or branched alkyl group having 1 to 6 carbon atoms, and R'' and R1 are each independently a hydrogen atom, a lower alkyl group, or a lower haloalkyl group. , X is an oxygen atom or a sulfur atom, ^ is a halogen atom or a straight-chain or branched alkyl group having 1 to 6 carbon atoms,
' is a hydrogen atom or a linear or branched alkyl group having 1-%-4 carbon atoms, 01 is an integer from 0 to 1,
Q is an unsubstituted or substituted 5-membered heterocyclic group containing 1 to 5 heteroatoms and bonded via a carbon atom (however, if it contains 2 or 5 heteroatoms, they are the same as each other) ) Maku represents an unsubstituted or substituted 6-membered heterocyclic group containing 1 to 3 nitrogen atoms and bonded via a carbon atom. ] 3(
2H)-pyridazinone derivatives, their production methods, and agricultural and horticultural insecticides and acaricides containing the derivatives as active ingredients;
This invention relates to nematicides, fungicides, and agents for killing mites parasitic on animals.

The present inventors previously discovered that 5 of a part of n represented by the following general formula
It was discovered that 12H1-pyridazinone derivatives have insecticidal, acaricidal, nematicidal, and bactericidal effects for agricultural and horticultural purposes. (Refer to European Patent Publication No. 0088584 and Japanese Patent Publication No. 60-4175) ○ RI' [In the formula, for example, R'7 is an alkyl group, A' is...a rogen atom, x9 is an oxygen atom or a sulfur atom, Rm and represent a hydrogen atom or a lower alkyl group. ] One of the characteristics of this known compound is a substituted benzyloxy group or substitution at the 5-position of the pyridazinone ring.The present inventors continued to search for pyridazinone derivatives. the result.

The general formula [512E represented by "ll"] containing a 5-membered heterocyclic group or a 6-membered heterocyclic group at the 5-position of the pyridazinone ring
(We have found that +-pyridazinone derivatives have dramatically stronger insecticidal, acaricidal, nematocidal, and bactericidal activities than the known compounds represented by the general formula closed above. The known compounds represented by the formula n are effective against powdery mildew and downy mildew, but the compounds of the present invention are effective against powdery mildew and downy mildew in addition to these.

It is also highly effective against rice blast, etc., and has a clearly wide spectrum of bactericidal activity. Moreover.

The present invention was completed by discovering that by introducing a 5-membered heterocyclic group or a 6-membered heterocyclic group into a pyridazinone derivative, it is possible to effectively control organisms harmful to agriculture and horticulture with extremely low drug concentrations.

Compounds included in the present invention include, for example, the compounds shown in Table 1. However, the compounds in Table 1 are for illustration purposes only, and the present invention is not limited thereto.

[However, in Table 1, Me stands for methyl group, Bit stands for ethyl group, 'kp'ro stands for globyl group i, 8u stands for butyl group, t stands for tertiary group, soil stands for iso, and S stands for secondary. ] Note that among the compounds included in the present invention, in the case of a compound having an asymmetric carbon atom, the optically active (tochi form or ←) form is also included.

Table 1 The compound numbers in Table 1 above are the production examples below.

Please refer to the formulation examples and test examples.

The compound of the present invention has the general formula [old: [In the formula, R and A have the same meanings as above.

Then... indicates an α-gen atom, -BH or -OH. ] and the compound represented by the general formula l]: L1 Indicates a halogen atom, -+3H or 10H. ] It can be produced by reacting with a compound represented by n. In general, the general formula [old! When is a halogen atom, use -day or -OH for X" in general formula 1; conversely, use X# in general formula [formerly -BH, -0HO, general formula It is preferable to use atoms. It is also preferable to carry out the reaction in the presence of a suitable base in a solvent that does not affect the reaction.

Next, the method for producing the adduct of the present invention and the raw material compound will be specifically explained with reference to Examples and Reference Examples, but the present invention is not limited to these.

Reference example 1 Raw material 2-t-butyl-5-fuclo-4-methyl-512
H) Synthesis of pyridazinone A Grignard reaction agent was prepared by dropping methyl iodide 55,3f (0.25 mol)'fr into a solution of magnesium & 0 flcL (25 mol) and dried tetrahydrofuran 50-2 under a nitrogen stream. After finishing dropping the methyl iodide, 1000 d of dry toluene was added. This solution t-6
Heat to 0 to 70°C, and then add methyl iodide dropwise until all magnesium is removed. The Grignard reagent was cooled to room temperature and 2-1-butyl-4,5-dichloro a
-5(2H1-pyridazinone 21,2,1t (11 mol)) was dissolved in dry toluene 200- and added dropwise over 20 minutes. After the dropwise addition, the reaction was carried out at room temperature for 1 to 3 hours, and then concentrated hydrochloric acid 100- The reaction solution was poured into a solution of 900 g of ice water and extracted.The organic layer was then washed with 500 g of 10X sodium hydroxide and 500 g of water, and then dried over anhydrous sodium sulfate.

The solvent was distilled off under reduced pressure to obtain crude product t-17.2f.

This crude product was distilled to a boiling point of 60-62℃/CL22s.
By further separating and purifying by column chromatography (silica gel; hexane-acetate 7N 15:1), the
(4.32 2H1-pyridazinone was obtained.

N5=1,3238 NMFt 1ODO4, TM31: 1.63L9
H, sl.

1,2,2515H,sl, 7.66+1H,sI
Reference example 2 Raw material 2-t-butyl-5-mercapto-4-methyl-3
Synthesis of (2H)-pyridazinone 2-1-butyl-5-ri-4-methyl-3 (2 days)-pyridazinone 17.
Of (1085 mol) and 70X sodium bisulfide a
st ((1106 mol) was added to ethanol 75-.

The mixture was stirred under reflux for 4 hours. After cooling, the mixture was poured into 500 d of ice water and extracted with 200 ml of ethyl ether.

The ether layer was washed with 100% water, dried over anhydrous sodium sulfate, and the solvent was distilled off to obtain crude products 1&3f.

NMR (ODOl, δ, TMI; 1.61 t
9Hs sl.

λ2515EI, sl, 7.46 (IH,, s1
M/Z; 198 (P+1. 145 (BPI) This compound was used as a raw material for the following production example without being purified.

Reference example 3 Raw material 2-t-butyl-5-hydroxy-4-methyl-5
Synthesis of (2H)-pyridazinone 2-t-butyl-5-ri-4-methyl-6(28)-pyridazinone 1,2,
0 fl (1 mole of LO) and potassium hydroxide 1,2,8
f (5 moles of CLO) was added to 50 mol of ethylene glycol and stirred at 130°C for 4 hours. Pour into 200 ml of cooled drained water, add 6N hydrochloric acid 2(ld), and collect the precipitated crystals by filtration. After drying, wash with 50 ml of hot isopropyl ether to obtain 2-t-butyl-5-hydroxy-4-methyl. -5
(2) 11-pyridazinone fe1.7f was obtained. Melting point:
256. Q~259.0℃ NMR (ODO4, δ, T
MI31 i 1.62 (9th, S).

1.97 (5H, al, 4.650H, sl.

7.60 (IH, s 1 M/Z; IEI2(P”l, 12718P+ Production Example 1 2-t-butyl-5-(5-t-butyl-2-thienylmethylthi-1-4-methyl-5 (2E (Production of l-pyridazinone (synthesis of the present compound l628) 2-t-butyl-5-mercapto-4-methyl-5t2
H1-pyridazinone LOW and 2-t-7'thyl-5
1.3 f of potassium carbonate was added to a solution of 20 dK of N-dimethylformamide and 1.9 f of α-comethylthiophene with stirring at room temperature. Further at room temperature 8
After stirring for an hour.

It was poured into 50ml of water and extracted twice with 50ml of benzene. The organic layer was washed with water, dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure to obtain crude product t-5,5f. 2-t-butyl-5-1
5-i-butyl-2-chenylmethylthio)-4-methyl-5(2H1-pyridazinone tl-2,2f was obtained.

Oily substance.

NMRI (!DC4, δ, TMS): 1.42 +
9)1. s), 1.61 (9M.

sl, 1,2,1415FI, s), 4.28(
2H, sl, 458 (IH, d, J-5th zl, 6
．． 7412H,d, ,T=5Hzl.

7:64 (IE(,sl Production Example 2 2-t-butyl-4-rioQ-5-16-7'0 pyridylmethylthio)-512H)-Production of pyridazinone (Preparation of the present compound washing 285) Synthesis) 2-t-butyl-4-chloro-5-mercapto-5 (2
To a solution of 1,2,2 f of H1-pyridazinone and 1.9 f of 5-chloromethyl-2-propyloki7-pyridine dissolved in 205 d of N,N-dimethylformamide, 1,3 f of potassium carbonate was added while stirring at room temperature. The mixture was further stirred at room temperature for 8 hours, poured into drained water, and extracted twice with Penzey 50IIt. The organic layer was washed with water, dried over anhydrous sulfuric acid, and then the solvent was distilled off under reduced pressure to obtain a crude product. This was recrystallized by adding isopropyl ether f to obtain 2-1-butyl-4-ri-5-16-brobyloxy-3-pyridylmethylthio l-5 (2H1-pyridazinone'iiQ f).

Melting point; 91,2,0~9&5℃ N&(R(C!DO4,δ, 7M81; 1.01
tss, t, J=7az+.

1,30-1,2,00 12H, ml, 1.62
(9th, 8), 4.21+01. d,
, T-9Hz+, 7,35-7.7511H, ml
.

7-66 (IH, al, al8118.a, J-2H
zl Production Example 3 2-t-butyl-4-aa-5-[(5-riCl0-
2-chenyl)-α-methyl-methylthio:]-3(2
Production of EIl-pyridazinone (synthesis of present invention metal compound 48) 2-t-butyl-4-riaa-5-mercapto-5 (2
H1-pyridazinone L2f and 2-chloro-5-(1
-Chloroethyl)thiophene'z,at was dissolved in 20 mg of N,N-dimethylformamide', and 1.32 g of potassium carbonate was added thereto under stirring at room temperature. Further, the mixture was stirred at room temperature for 8 hours, poured into 50Mt of drained water, and diluted with benzene 507.
Extracted twice. Wash the organic layer with water and anhydride '411II2)
After drying with IJum, the solvent was distilled off under reduced pressure to obtain a crude product. By separating and purifying this t'L by column chromatography (silica gel: benzene), 2-1-butyl-4-lya-5-[(5-lya-2
-chenyl)-α-methyl-methylthio]-512Ei
)-pyridazinone 1, 2, 5f were obtained. Oily substance.

NMR (C! Do/,,, J, TMBL i 1.
60 (9H, al, 1.75 (AH.

d, ffx7Hzl, 4.87 (IH, q, J
s++7Hzl.

&7G (IH, d, :l-5Hz), &85
tlHs a, J-5Hz), 7.61 (IH,
sl Production Example 4 2-t-butyl-4-chloro-5-[6-(4-ri c1
clphenoxy)-3-pyridylmethyloxy]-3(
Production of 2EIl-pyridazinone (Compound of the present invention 551
synthesis) 2-t-butyl-4-riaa-5-hydroxy-5(2
1)-Pyridazinone 2-1 t, 5-poomethyl-2-14-rio a 7 znoxy)-pyridi y 1
, 2,5 f and potassium carbonate 1,3 t i N.

In addition to N-dimethylformamide 20-80-90℃
The mixture was stirred for 2 hours. After cooling, it was poured into 50 g of water and extracted twice with 150 g of benzene. The organic layer was washed with water, dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure to obtain a crude product. In this case, inpropyl ether and 2-
Add a mixed solvent of propatool and recrystallize to obtain 2-t-butyl-4-chloro-5-[6-(4-chlorophenoxy)-3-pyridylmethyloxy]-3(2H1-pyridazinone fc55f). Just in case.

Melting point: 15 (LO~154.3°C.

NMR1ODC4, δ, 7M31; 161 (9
F(, sl, !L21 (2H, sl, 485 hair, 40158. Qll, 7.65-7.85+1
H, ml, 7.72 (IH, sl, al511H
, d, : J = 2 days 2) Production example 5 4-ri aa-5-[s-+4-ri OQ benzoyl l -
2-fenylmethyloxic]-2-ethyl-3(2H)
-Production of pyridazinone (synthesis of the present invention compound 54) 4-chloro-2-ethyl-5-hydroxy-512H1
-pyridazinone 1.9f, 2-pcumomethyl-5-(4
-chlorobenzoyl)-thiopheno52f and potassium carbonate 1,3f't-N'.

In addition to N-dimethylformamide 20a+j, 50-6
The mixture was stirred at 0°C for 2 hours. After cooling, pour into water 5 (ld),
Extracted twice with 50ml of benzene. After washing the organic layer with water and drying over anhydrous sodium sulfate, the solvent was distilled off under reduced pressure to obtain a crude product i4. Of got it. t'Lfr: 4-('-I: IeI benzoyl 1-2-fenylmethyloxy)-2-ethyl-312FIl-pyridazinone I got i1F.

Melting point: 16aO to 16a5°C.

NMRIODO4,J, TMBL; 1,35 (
5H, t, J=7Hz +.

4.2112FI, q, I-7th zl, i Otsu (2H
,sl.

7.25 Hair, 95 +6H, ml, al2 tI
H, sl Production Example 6 2-i-buty/L; -5-(6-14-fluorobenzyloxy)-3-pyridylmethyloxy]-4-methyl-3(2H1-pyridazino/Production of Synthesis of Figurine 299) 6-(4-fluorobenzyloxy)-3-pyridinemethanol 13f'iM was dissolved in N-dimethylformamide 20- and 55X sodium hydride (1 [in mineral oil) at 0°C with stirring. L5F was added. After stirring at room temperature for 60 minutes, 2-1-butyl-5-riI
:+rho-4-methyl-3(2H)-pyridazinone 1,2
,0 f fr:N,M-Dimethylformamide 5 was added dropwise to the solution and stirred roughly at room temperature for 8 hours. It was poured into 50ml of ice water and extracted twice with 50ml of benzene. The organic layer was washed with water, dried over anhydrous sulfuric acid, and then the solvent was distilled off under reduced pressure to obtain 58 f of a crude product. By separating and purifying this using thin layer chromatography (silica gel: Pe/Zen), 2-1-butyl-5-[6-
(4-fluorabenzyloxy1-3-pyridylmethyloxy)-4-methyl-3(2H)-pyridazino/1
,2,5 were obtained.

Oily substance.

NMRI 0DC4, δ, TMSl; 1.65 t
9 H-s lp'2-0215H, sl, 5.
0912E (, sl, 5, 34 (2nd, S).

&75~7.80 (6H, ml, 7.78 (IH
, s l, a21 (1H, d, J-28zl Production example 7 2-t-butyl-4-riCl0-5-[6-14-fluorobenzyloxy)-5-pyridylmethyloxy)-
5128 Production of 1-pyridazinone (Synthesis of the present invention Somowashi 500) 6-(4-fluorobenzyloxy)-3-pyridinemethanol 1,2,3fiN,N-
55X sodium hydride (in mineral oil) a, sr'l was added to the solution in dimethylformamide 207 at 0° C. with stirring. After stirring at room temperature for 50 minutes, 2-1-butyl-4,5
-dichloro-5(2H1-pyridazinone 1,2,2fi
The mixture was further stirred at room temperature for 8 hours. It was poured into ice water 5ad and extracted twice with Penze 150d. The organic layer was washed with water, dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure to obtain 4.12% of the crude product. Add isopropyl ether to this and recrystallize it to obtain 2-t-butyl-4-cI.
ct-5-(6-14-fluoropenzyloxy7)-5
-pyridylmethyloxy]-3(2H)-pyridazino/
Get 52F.

Melting point: 121.0-124.0°C.

NMRI: ('DC4, δ, TM81; 1.6
2(9H, sl, a25(2E(.

s l, 5,35 +2H, s l, 475~7.
8516H, all.

7.89 (IEi, al, a260H, d, J
-2Hz) Next, production examples of compounds produced according to any of the methods of Examples 1 to 7 are shown in Table 2 along with their melting points and 'HNMR data. Compound numbers correspond to Table 1.

Table 2 (Example 4!!!) When using the compound of the present invention as an insecticide, acaricide, or nematicide for farm use, it is generally necessary to use an appropriate carrier. 2 For example, clay, talc, bentonite.

Solid carriers such as diatoms or water, alcohols (methanol, ethanol, etc.), aromatic hydrocarbons (penze/,
Toluene, xylem; can be applied in combination with liquid carriers such as tetrahydrocarbons, ethers, keto 7s, esters (ethyl acetate, etc.), acid amides (dimethylformamide, etc.), emulsifier 9 dispersant if desired;
By adding suspending agents, penetrating agents, spreading agents, stabilizers, etc., liquid formulations,
It can be put to practical use in any dosage form such as an emulsion, a wettable powder, a two-grain powder, or a flowable preparation. In addition, other types of herbicides, various insecticides, fungicides,
It may also be used in combination with a growth regulator, synergist, etc.

The amount of the compound of the present invention to be applied depends on the application situation and application period.

There are differences depending on the application method, target pests, cultivated crops, etc., but in general, the amount of active ingredient is 1005~100% per hectare.
A value of 5 is appropriate.

Next, examples of distribution of disinfectants, insecticides, acaricides, nematicides, and insecticides for killing mites parasitic on animals containing the compound of the present invention as an active ingredient will be shown, but the present invention is not limited to these. In addition,
In the distribution examples below, "parts" mean parts by weight.

Distribution example 1 Emulsion compound of the present invention ・・・・・・・・・・・・・・・・・・
・・・・・・・・・ 15 parts xylene ・・・・・・・
・・・・・・・・・・・・・・・・・・ 60 copies N, N
-Dimethylformamide ・・・・・・・・・・・・・・・
・ 20 parts Tsurupol 2680 ・・・・・・・
・・・・・・・・・・・・・・・・・・ 5 parts (mixture of nonionic surfactant and anionic surfactant 2 Toho Chemical Industry ■Product name) Mix the above uniformly. and make an emulsion. When used, the above emulsion is diluted 500 to 20,000 times and spread so that the amount of active ingredient is α005 to 5-5 per hectare.

Distribution example 2 Irrigation agent Compound of the present invention ・・・・・・・・・・・・・・・・
・・・・・・ Part 20 Sieglite PIFP ・・・
・・・・・・・・・・・・・・・・・・・・・ 75
Part (kaori/based clay: Sieglite Industries ■Product name 1 Nlupole 5039 ・・・・・・・・・・・・・・・
・・・・・・・・・・・・ 5 parts (Mixture of nonionic surfactant and anionic surfactant 2 Toho Chemical Industry ■Product name) Sunextract P-201・・・・・・・・・・・・...
... 2 parts (Calcium lignin sulfonate: Yamaba Kokusaku Pulp ■Product name) The above is uniformly mixed and pulverized to make a wettable powder. When used, the above-mentioned hydrating agent is diluted to ~20,000 times and sprayed so that the amount of active ingredient is α00 to 5 times per hectare.

Distribution example 3 Oil agent Compound of the present invention ・・・・・・・・−・・・・・・・・・・
・・・・・・・・・ 50 parts Methylcelonorp・
・・・・・・・・・・・・・・・・・・・・・・・・
Uniformly mix 50 parts or more to make an oil agent. When using, use the above oil in an amount of active ingredient or 100% per hectare.
Scatter it until it becomes ~5 yen.

nAnal powder Compound of the present invention・・・・・・・・・・・・・・・・・・
-・40 parts Carplex (anti-caking agent) 1.・・・
・・・ 05 giri -
・・・・・・・・・・・・・・・・・・・・・・・・
95 parts diisopropyl phosphate...
・・・・・・・・・・・・ 1.3 parts or more are uniformly mixed and ground to make a powder. For toilet use, the above-mentioned powder is sprinkled at an amount of active ingredient of 1005 to 5 hours per hectare.

j1dan"1" - Granules Compound of the present invention ・・・・・・・・・・・・・・・・・・
・・・－・・・・・・ 5 parts bentonite ・・・
・・・・・・・・・・・・・・・・・・・・・・・・ 54
Department information...
・・・・・・・・・・・・・・・ 40 parts Calcium lignia sulfonate ・・・・・・・・・
At least 1 part is uniformly mixed and pulverized, a small amount of water is added, the mixture is stirred, the mixture is granulated using an extrusion type granulator, and the mixture is dried to form granules. When used, the above-mentioned granules are dispersed so that the amount of the active ingredient becomes 900 to 5kII per hectare.

Distribution example 6 Flowable agent Compound of the present invention ・・・・・・・・・・・・・・・・
・・・・・・・・・ Part 25 Tsurupol 5555 ・
・・・・・・・・・Song... 10 parts (Nonionic surfactant: Toho Chemical Industry ■Product name) Lunosis 10
000 ・・・・・・・・・・・・・・・・・・・・・
・ Part a5 (Anionic surfactant: Toho Chemical Industry ■
Product name: 11X xanthan gum aqueous solution ・・・・・・・・・
・・・・・・ 20 parts (natural polymer) Water ・・・・・・・・・・・・−・・
・・・・・・・・・・・・・・・ 44.3 parts I? ! Then, the compound of the present invention is added thereto, thoroughly stirred, and wet-pulverized in a sand mill to obtain a flowable agent.

When using the above flowable agent,
When diluted twice, the amount of active ingredient is 9 per hectare (LOO5
Scatter it until it becomes ~10 yu.

The compound of the present invention is used for Hemiptera pests such as leafhopper, Lepidoptera pests such as diamondback moth, and Biptera pests.

It has excellent insecticidal power against sanitary pests and insects such as Culex mosquito, as well as various mites that parasitize fruit trees and canola.
Two-spotted spider mite, Kanzawa/% mite.

False spider mite, citrus spider mite, apple spider mite, etc., and mites parasitic on animals, such as the American spider mite, Boophilus aniereitas, Amplionma maculatum,
It is also effective in controlling Libicephalus, Appendiculatus, and Thysophyllum ticks. A major feature of the compounds of the present invention is that in addition to the above-mentioned insecticidal and acaricidal effects, they are also effective in controlling diseases of fruit trees and cane crops, such as powdery mildew, downy mildew, rust, and blast. Therefore, it is an excellent agricultural chemical having properties that can be achieved when the present invention is developed.

Also, livestock such as cows, horses, and sheep (2g), and poultry.

It is also an excellent exterminator for mites that infect animals such as dogs, cats, and rabbits.

This will be specifically explained in the following test examples.

Test Example 1 Insecticidal test against black leafhopper A rice mold nest was immersed in an emulsion of the compound of the present invention at a concentration of 1000 ppm for about 10 seconds, and the mold nest was placed in a glass cylinder to determine the resistance to organophosphorus insecticides. Released 10 adult leafhoppers with the following.

Covered with a nine-hole plastic case back. This cylinder is 2
The animals were housed in a stellar chamber at 5°C, and the mortality rate after 96 hours was calculated using the following formula. The test was conducted in two sections. The results are shown in Table 3.

Test Example 2 Contact Insecticidal Test against Nijeuya chinensis Tomato leaves were immersed in a water emulsion of the compound of the present invention at a concentration of 1000 ppm for about 10 seconds, air-dried, placed in a Petri dish, and Nijeuya nigra were placed in a petri dish. Kill 10 2nd instar ladybug larvae per petri dish.

The animals were placed in a thermostatic chamber at 25°C with holes in them, and the mortality rate after 96 hours was calculated using the following formula.

The test was conducted in two sections. The results are shown in Table 3.

Insect Killing Number Test Example 3 Acaricidal Efficacy Test against Zawa spider mites A green bean leaf was cut into 1 to 3 circles in diameter using a leaf patch and placed on a damp paper on a styrene cup with a diameter of 71 mm. Add Kanzawa spider mite larvae per leaf to this
0 animals were vaccinated. Half a day after inoculation, a chemical solution prepared by diluting the emulsion of the compound of the present invention with a spreading agent to a concentration of 11,000 pp was sprayed using a rotary scattering tower at a rate of 2 cups per styrene cup, and the mortality rate after 96 hours was calculated using the following formula. I asked for it.

The test was conducted in two sections.

The results are shown in Table 3.

(m) Insecticidal test against Spodoptera larvae A leaf of Callanus was immersed in a 1000 ppm water emulsion of the present invention at 8 degrees Celsius for about 10 seconds, air-dried, and then placed in a petri dish. The animals were placed in a constant temperature room at 25°C with the lid open, and the mortality rate after 7 days was calculated using the following formula. In addition, the test is 2
It was done by ward system.

The results are shown in Table 3.

Table 3 Test Example 5 Nematicidal Efficacy Test against Nematode Nematode Contaminated soil with Nematode Nematode was placed in a styrofoam cup with a diameter of 8. Dilute the uninvented emulsion with water and
Adjust the chemical solution with a concentration of 00 ppm.

A spreading agent was added and irrigated into the soil at 50 ml per styrofoam cup. After 48 hours had elapsed, the indicator crop, tomato seedlings, was transplanted. After 30 days had passed, the roots of the tomato plants were washed with water and an inspection was conducted to determine whether they were infested with cathoppers. The test was conducted in two sections. As a result, it was found that the following compounds exhibited strong nematocidal activity with almost no nematodes observed @Compound of the Invention 541, 2, Negative 123. Return 246. Demon 2
87, )ffi551.

Test Example 6 Cucumber and disease control test Chemical solution 1100 prepared by adjusting two inventive food emulsions to a specified concentration using cucumber (variety: Sumo Hanshiro) grown in pots for 2 weeks
0 ppm l was sprayed per 20 m/body. The cucumbers were kept in a greenhouse for one day, and the cucumbers and diseased bacteria (Pseudo) were grown.
Inoculation was performed by spraying a spore suspension (15 spores per field of view at 150x magnification) of Doparonospora cubensis. The cucumbers and the cucumbers inoculated with the spores of the disease fungus were placed in a room at 25°C and 100x relative humidity for 24 hours, and then moved to a greenhouse to wait for the onset of disease. The degree of morbidity was investigated 7 days after vaccination. As a result, no disease onset was observed with the following compounds.

Washing with the compound of the present invention 44. Ya231. Wash 246. wash 285,
1lli286,4287. A299,4500゜4
551゜Test Example 7 Cucumber Udon and Disease Control Test Using cucumbers (variety: Sagami Hanshiro) grown in pots for 2 weeks, 11,000 pp of a chemical solution adjusted to a predetermined concentration of the compound emulsion of the present invention was sprayed at 20 Int per pot. The cucumbers were kept in a greenhouse for one day, and the cucumber udon and diseased bacteria tS meat aerothec
The cucurbits were inoculated by spraying a spore suspension of A. fuliqiaea l (25 spores per field of view at 1150x magnification) and placed in a greenhouse with 25 to 500 cells to wait for the onset of disease. The degree of morbidity was investigated 10 days after inoculation. the result.

No onset of disease was observed when using the following compounds.

Inventive accessories &28. 44. Ryo 57. Demon 251° Boiled 2
45. &246. Grave 285. Black 286. Magic 287° Black 2
99. ．． /ll;, 500. Ya551. Ya 352゜Test Example Day Wheat Rust Control Efficacy Test Wheat (Norin No. 61, 3rd to 4th leaf stage) grown in a pot with a diameter of 90 was treated with a chemical solution prepared by adjusting the concentration of 2 inventive emulsions to a concentration of 1000 ppm. A spray gun was used to spray 20ml per pot.

The day after spraying, the wheat rust fungus (Puccinia tr.
iticim) Summer spore suspension 11 x 150, 50 pieces/field)'fr: Sprayed and placed in an inoculation box at a temperature of 25°C and a humidity of 955X or higher overnight. Thereafter, it was placed at room temperature, and the area of diseased spots formed 10 days after inoculation was measured, and the control value was calculated according to the following formula.

As a result, the following compounds showed a control value of 100X.

Inventive accessory 44. No1251. Ya246. Muku85
．． Ya286. Point 287. Wash 299. 300゜A351
．． A552゜Test Example 9 Rice blast control effect test Rice (Nipponbare 6-4 leaf stage) grown in pots with a diameter of 9cn1 was treated with a chemical solution adjusted to a concentration of 1000 ppm using a spray gun. 2 per pot
0 - Spread. The day after spraying, rice blast fungus I Pyri
-: ultrLa oryzael spore suspension (×15
0.40@/field of view) t-spray, temperature 25°C.

The seeds were placed in an inoculation box with a humidity of 95X or higher overnight. After that, leave it at room temperature and touch it? ! ! The number of diseased spots formed after 7 days was measured, and the total pest control was calculated according to the following formula.

As a result, the following compounds showed a control value of 100X.

Compound of the present invention A44. /ra251. g246.
5285.4286. Jii287,4299. A30
0° & 518. Test Example 10 Cucumber and Disease Control Effect Test (Low Concentration Test) Same as Test Example 6. However, the concentrations of the two compounds and the control compound were 500, 100 and 50 ppp, respectively.
It was set as m. The control value was calculated according to the following formula.

The results are shown in Table 4. As a result, it can be seen that the additive of the present invention exhibits extremely strong bactericidal activity compared to the publicly available control additive.

Test Example 11 Powdery Mildew Control Efficacy Test (Low Concentration Test) Based on Test Example F. However, the concentrations of the two compounds of the present invention and the control compound are 500, 100 and 50 pp, respectively.
It was set as m. The control value was calculated according to the following formula.

The results are shown in Table 4. The results show that the compound of the present invention exhibits extremely strong bactericidal activity compared to the known control compound.

Test Example 12 Wheat Rust Control Efficacy Test (Low Concentration Test) Same as the test example date. The concentrations of the fc stock 1 compound and control compound were 500, 100 and 50 p, respectively.
It was set as pm. One song of pest control was calculated according to the following formula.

The results are also shown in Table 4. The results show that the two compounds of the present invention exhibit extremely strong bactericidal activity compared to known control compounds.

Test Example 13 Rice blast control effect test (Low concentration test 1 Same as Test Example 9. However, the concentrations of the uninvented compound and the control compound were 500, 100, and 50 po, respectively.
I said it. The control value was calculated according to the formula in F.

The results are shown in Table 4. As a result, it can be seen that the compound of the present invention exhibits extremely strong bactericidal activity compared to the known control compound.

Table 4 a1 Compounds described in Japanese Patent Publication No. 1988-4175 and chemical adducts within the scope of claims b) Compounds described in European Patent Publication No. 0088384 and compounds within the scope of claims 1 result of Test Examples 1O to 13 Compared to the control compound, the invented compound not only has much stronger activity against each disease, but also has a broader spectrum; It was found that it has an excellent bactericidal effect that can simultaneously control disease and rust.

333-U” - Insecticidal test against black leafhopper (
Low concentration test) According to Test Example 1. However, the concentrations of the two compounds of the present invention and the control compound were 100 ppcn.

The results are shown in Table 85.

Results 9 It can be seen that the compound of the present invention exhibits stronger insecticidal activity compared to the known control compound.

Test Example 15 Insecticidal test against Kanzawa spider mite (low concentration test) Same as Test Example 3. However, the concentrations of the two adducts of the present invention and the control compound were 100 ppm.

The results are shown in Table 5.

Table 5

Claims (10)

[Claims] (1) General formula [I]: ▲There are mathematical formulas, chemical formulas, tables, etc.▼ [I] [In the formula, R is a hydrogen atom or a linear or branched alkyl group having 1 to 6 carbon atoms, R^1 and R^2 each independently represent a hydrogen atom, a lower alkyl group or a lower haloalkyl group, X represents an oxygen atom or a sulfur atom, A represents a halogen atom or a linear or branched alkyl group having 1 to 6 carbon atoms, B has ▲mathematical formula, chemical formula, table, etc.▼ group, -CR^1R^4O- group or -CR^2R^
4-CR^3R^4- group, R^2 and R^4 each independently represent a hydrogen atom or a linear or branched alkyl group having 1 to 4 carbon atoms, m is an integer of 0 or 1,
Q is an unsubstituted or substituted 5-membered heterocyclic group containing 1 to 3 heteroatoms and bonded via a carbon atom (however, if it contains 2 or 5 heteroatoms, the heteroatom may be the same or different from each other) or an unsubstituted or substituted 6-membered heterocyclic group containing 1 to 5 nitrogen atoms and bonded via carbon atoms. ] A 3(2H)-pyridazinone derivative represented by: (2) In the general formula [I], Q is an unsubstituted or substituted 5-membered heterocyclic group containing 1 to 3 heteroatoms and bonded via a carbon atom (however, an unsubstituted or substituted 5-membered heterocyclic group containing 2 or 3 heteroatoms 3(2H) described in claim (1), which may be the same or different from each other.
-Pyridazinone derivatives. (3) In the general formula [I], Q is a 5-membered heterocyclic group such as thiophene, furan, pyrrole, pyrazole, imidazole, thiazole, oxazole, isothiazole, isoxazole, 1,2,3-triazole, 1,2,4 −
triazole, 1,3,4-triazole, 1,2,3
-thiadiazole, 1,2,4-thiadiazole, 1,
2,3-thiadiazole, 1,3,4-thiadiazole, 1,2,4-oxadiazole, furazan or 1,
Claim No. 2 which is 3,4-oxadiazole
3(2H)-pyridazinone derivative according to item ). (4) In the general formula [I], Q is an unsubstituted or substituted 6-membered heterocyclic group containing 1 to 3 nitrogen atoms and bonded via a carbon atom, Claim No. 1 3(2H)-pyridazinone derivative according to item ). (5) In the general formula [I], Q is a 6-membered heterocyclic group such as pyridine, pyridazine, pyrimidine, pyrazine, 1,2,4
The 3(2H)-pyridazinone derivative according to claim (4), which is -triazine or 1,3,5-triazine. (6) In the general formula [I], Q is unsubstituted or a halogen atom, a linear or branched alkyl group having 1 to 6 carbon atoms, a cycloalkyl group, a cycloalkyloxy group, or a cycloalkyloxy group having 1 to 6 carbon atoms a straight-chain or branched alkyloxy group or alkylthio group, a straight-chain or branched alkylsulfinyl group or sulfonyl group having 1 to 6 carbon atoms, a lower haloalkyl group, a lower haloalkyloxy group or a haloalkylthio group, a lower alkenyloxy group , trimethylsilyl group, lower alkoxycarbonyl group, dimethylamino group, nitro group, cyano group, ▲
There are mathematical formulas, chemical formulas, tables, etc. ▼, -OCH_2, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼, ▲
There are mathematical formulas, chemical formulas, tables, etc. ▼, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼, ▲ Mathematical formulas, chemical formulas,
There are tables, etc.▼ (However, Z is a halogen atom, lower alkyl group, lower alkoxy group, cycloalkyl group, lower haloalkyl group, lower alkoxycarbonyl group, or nitro group, and l is 0.
Alternatively, it represents an integer of 1 to 5, and when l is 2 to 5, Z may be the same or different from each other. ) The 3(2H)-pyridazinone derivative according to claim (1), wherein the 3(2H)-pyridazinone derivative is substituted by (7) The 3(2H)-pyridazinone derivative according to claim (1), wherein m=0 in the general formula [I]. (8) The 3(2H)-pyridazinone derivative according to claim (1), wherein m=1 in general formula [I]. (9) General formula [II]: ▲There are mathematical formulas, chemical formulas, tables, etc.▼ [II] [In the formula, R is a hydrogen atom or a linear or branched alkyl group having 1 to 6 carbon atoms, and A is a halogen. An atom or a linear or branched alkyl group having 1 to 6 carbon atoms, and X' represents a halogen atom, -SH or -OH. ] Compounds represented by the general formula [III]: ▲Mathematical formulas, chemical formulas, tables, etc.▼[III] [In the formula, R^1 and R^2 each independently represent a hydrogen atom, a lower alkyl group, or a lower Haloalkyl group, B is ▲
There are mathematical formulas, chemical formulas, tables, etc. ▼ group, -CR^3R^4
O- group or -CR^2R^4-CR^3R^4- group, m represents an integer of 0 or 1, Q contains 1 to 3- hetero atoms, and is bonded via a carbon atom. unsubstituted or substituted 5-membered heterocyclic group containing 2 or 3 heteroatoms (which may be the same or different from each other) or containing 1 to 5 nitrogen atoms and containing 1 to 5 carbon atoms Represents an unsubstituted or substituted 6-membered heterocyclic group bonded via an atom, X'' is a halogen atom, -SH or -OH
shows. ] General formula [I]: ▲There are mathematical formulas, chemical formulas, tables, etc.▼[I] [In the formula, R is a hydrogen atom or a direct R^1 and R^2 each independently represent a hydrogen atom, a lower alkyl group, or a lower haloalkyl group; X represents an oxygen atom or a sulfur atom; and A represents a halogen atom or a carbon atom having 1 to 6, a linear or branched alkyl group, B is a ▲mathematical formula, chemical formula, table, etc.▼ group, -CR^3R^4O- group, or -CR^3R^
4-CR^1R^4- group, R^3 and R^4 are a hydrogen atom or a linear or branched alkyl group having 1 to 4 carbon atoms, m is an integer of 0 or 1, and Q is 1 An unsubstituted or substituted 5-membered heterocyclic group containing ~5 heteroatoms and bonded via a carbon atom (however, if it contains 2 or 3 heteroatoms, they may be the same or different from each other) ) or represents an unsubstituted or substituted 6-membered heterocyclic group bonded to ] 3(2H
)-Production method of pyridazinone derivative. (10) General formula [I] ▲Mathematical formulas, chemical formulas, tables, etc.▼[I] [In the formula, R is a hydrogen atom or a linear or branched alkyl group having 1 to 6 carbon atoms, R^2 each independently represents a hydrogen atom, a lower alkyl group or a lower haloalkyl group, X represents an oxygen atom or a sulfur atom, A represents a halogen atom or a linear or branched alkyl group having 1 to 6 carbon atoms, B ▲There are mathematical formulas, chemical formulas, tables, etc.▼ group, -CR^3R^4O- group or -CR^3R^
4-CR^3R^4- group, R^3 and R^4 each independently represent a hydrogen atom or a linear or branched alkyl group having 1 to 4 carbon atoms, m is an integer of 0 or 1,
Q is an unsubstituted or substituted 5-membered heterocyclic group containing 1 to 3 heteroatoms and bonded via a carbon atom (however, if it contains 2 or 3 heteroatoms, they are the same as each other) ) or an unsubstituted or substituted 6-membered heterocyclic group containing 1 to 3 nitrogen atoms and bonded via a carbon atom. ] An agricultural and horticultural insecticide, acaricide, nematocide, fungicide, and an insecticide for controlling mites parasitic on animals, which contain one or more of the following 3(2H)-pyridazinone derivatives as an active ingredient.