JPS6216470A - Pyridazinone derivative, production thereof and insecticidal and miticidal agent containing same - Google Patents

Abstract

NEW MATERIAL:The 3(2H)-pyridazinone derivative of formula I (R is 2-6C alkyl; R<2> and R<2> are H or lower alkyl; X is halogen; R<3> is H, halogen, lower alkyl or lower alkoxy; R<4> is 3-12C alkyl, alkenyl, 3-6C cycloalkyl or cycloalkenyl; Y is O, S, S=O or O=S=O; m is 1-4; n is 0 or 1; when n=0, R<4> is 7-12C alkyl). EXAMPLE:4-Bromo-2-t-butyl-5-(4'-i-propoxybenzyloxy)-3(2H)-pyridazinone. USE:Insecticidal and miticidal agent. PREPARATION:The compound of formula I can be produced by reacting the compound of formula II (A is halogen or OH) with the compound of formula III (B is halogen or OH).

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a novel 3(2a)-pyridazino/derivative, its production method, and agricultural and horticultural insecticides, acaricides, nematicides, fungicides, and animal pesticides containing the derivative as an active ingredient. This relates to an exterminator for mites that parasitize. More details.

General formula (I): [wherein, R is a linear or branched alkyl group having 2 to 6 carbon atoms, R1 and Ro are each independently a hydrogen atom, 9 is a lower alkyl group, X is a halogen atom, R
1 is a hydrogen atom, a rogen atom.

A lower alkyl group or a lower alkoxy group, Ro is a linear or branched alkyl group or alkenyl group having 3 to 120 carbon atoms, and 6 to 6 carbon atoms represents an integer of 1 to 4; 9
When m is 2 to 4, R1 may be the same or different. n
indicates 0 or 1. However, when n is 0, Ro represents an alkyl group having 7 to 12 carbon atoms. ] 3(2H
)-pyridazinone derivatives, their production methods, and agricultural and horticultural insecticides, acaricides, nematocides, fungicides, and insecticides for killing mites parasitic on animals, which contain the derivatives as active ingredients.

The present inventors previously discovered that some 5(
2K)-pyridazinone derivatives are used as insecticides and acaricides for agricultural and horticultural purposes.
It was discovered that it has nematicidal and bactericidal effects (European Patent Publication No. 0088384).

This known compound is relatively toxic to fish;
As a result, the present inventors continued to conduct intensive research on pyridazinone derivatives, and found that the compound of the present invention represented by general formula (I) has excellent insecticidal and killing properties. Tick.

It has been found that it has nematicidal and bactericidal effects, has stronger activity than the known compounds represented by general formula (IV), and has low toxicity to fish. That is, the compound of the present invention represented by the general formula (1) can effectively control organisms harmful to agriculture and horticulture at extremely low drug concentrations,
The present invention was completed based on the discovery that it is also highly safe for fish. Examples of the compounds included in the present invention include 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 is a methyl group i, and Kt is an engineering group.
Chyl group, Pro is propyl group, Eh is butyl group.
Pen stands for Pentyl Fund, Hex stands for Hexyl Fund.

ti stands for meta-year, 1 stands for iso, 8 stands for secondary, and n stands for normal. ] Among the compounds included in the present invention, in the case of a compound having an asymmetric carbon atom, the optically active (+) or ← isomer is also included.

Table 1 Next, the method for producing the compound of the present invention will be specifically explained with reference to Examples, but the present invention is not limited to these.

-1-proboxybe/zyloxy)-5(2H)-pyridazinone (synthesis of the present compound M4) 4-1-7''roboxypenzyl alcohol t7f (CL
O1 mol) total N, 1ll-dimethylformamide 2
55x Sodium hydride (in mineral oil) asf was added under stirring at 0°C to 0dKAI. After stirring at room temperature for 50 minutes, 2-t-butyl-4,5-dibromo-5 (2H)
- A solution of pyridazinone 51f (,101 mol) dissolved in 10rnt of N,N-dimethylformamide is added dropwise,
The mixture was further stirred at room temperature overnight. It was poured into ice water and extracted with be/zee/. The Ben9f layer was washed with water, dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure to obtain a crude product. This was recrystallized from a t-n-hexane/zene mixed solvent to obtain the target compound i1F. Melting point 11 & 7%-1
126℃ NMR (cna4, 3.7M8) i i,
35 (6H, ld, J-6Hz) 1.61 (9H, s
), 455 (IH, q-q, J -6Hz), a
25 (2L 8), 198 (2H, d.

, TW9Hz), 7.33(2H,d, Jx9az
).

7.67 (IL8) Production Example 2 Production of 2-t-butyl-4-chloro-5-(2'-1-propylthiobenzyloxy)-3(2H)-pyridazinone (synthesis of present compound 414) 2 -t-butyl-4-chloroa-5-hydroxy-#?
&3(2H)-pyridazinone 1 of (α01 mol) and 2-1-probyltheobenzylchlor IJ)'2. OF(
α01 mol) was added to 30 charcoal of N,N-dimethylformamide, and then potassium anhydride Z and OFi were added.
The mixture was stirred at 00°C to 120°C for 3 hours.

After the reaction, the mixture was poured into water and extracted with benzene.

The be/ze/layer was washed with 5X aqueous sodium hydroxide solution, washed with water, dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure to obtain 15ff of a crude product. This is purified by column separation (
(benzene-ethyl acetate) to obtain the target compound 2
．． 5 no? Nine points. M”=1.5B58uMR(aDC6
,,δ,TM8) ; 1.28(3H,d, ,T-
7Hz) 1.62 (9H, s), 135 (IH, q-
q, J=7Hz) 5.43 (2H, 8), 7.15
~7.65 (4L m) 7.75 (IH, θ) lWataruto2-t-7'ke/I/-4-p. . -5-(
2'-1-7' lobilsulfonyl/silo? )−
Production of 3(2H)-pyridazino/ (synthesis of compound 16 of the present invention) 2-t-Butyl-4-chloroO-5 obtained in Production Example 2
-(2'-i-probylthiobenodyloquine)-3(
2H)-pyridazino71. At (α005 mol) was dissolved in dicumylmeth/2QadK, and 1.9F (11011 mol) of 9m-chloroα-benzene, -1 aromatic acid was added thereto at room temperature.
The mixture was stirred for several days.

An aqueous solution of hydrogen sulfite was added to the reaction solution, and the organic layer was separated, washed with an aqueous sodium hydroxide solution, washed with water, and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure to obtain 1.8ff of the target compound! :Obtained.

Melting point 14 & 0~14EL °C NMR ((!DC4, δ, TM8) i 1jl(
3H, (L, J-7Hz) 1.65 (9H, s),
A40(H(,q-q,J=7H2)5.75(2H,
a), 7.45 to a20 (4H, m) 7.91 (IH
,s) Production row 4 2-t-butyl-4-chloroa-5-(3'-ria-row4
'-1-7'o Hoshibe/Jirokiku)-5 ('2H)
-Production of pyridazinone (synthesis of present invention compound wash 19) Instead of 2-1-pucupylthiobe/dyl chloride in Production Example 2, 3-chloroa-4-1-proboquicupe/dyl chloride 2.2 f ((101 mol>5e- The crude product obtained by carrying out the same operation as above was washed with n-hexane to obtain the desired product 50F.

Melting point 9'16~104.2℃ NMR (0DO4, δ, TMS); 1.35 (6
H, d, J=6az) 1.65(91(,a), 4
．． 56 (IH, q-q, I=6H2) 5.20 (2H
, s), A80~7.40 (IH, m) 7.65 (1+
(,a) -improboxy3'-methoxybenzyloxy)-
Production of 3(2H)-pyridazinone (Invention Hardware Store 21)
Synthesis of 2-t-butyl-4,5-dicoa-3(2H)-pyridazyl alcohol 2.2r ((101 mol) and 4-1-10boquino-5-methoxybenzyl alcohol 2.0r(10
1 mol) of N,N-dimethylformamide 30I! 11
0.7 f of potassium hydroxide powder dissolved in
jib and stirred overnight at room temperature. Extracted with 15 gk Akebe/Ze/ in ice water.

Wash the be/ze/layer with aqueous sodium hydroxide solution.

After washing with water and drying over anhydrous sodium sulfate, all the solvent was distilled off under reduced pressure. The obtained crude product was washed with hexane to obtain the target compound 5.Of.

Melting point 992-106.8°C NMR (cDc4.δ, TMS); 1.41 (6
t(,d, Jja61(Z)1.60 (9L s
), 569 (5H, Sun), 4.44 (IH, q-q
, J=6H2), 5.21 (2L s) 1.66
Hair, 00 (5H, m), 7.70 (LHoa
)-Chloboxybenzyloxy)-5(2H)-pyridazinone (Synthesis of Compound 54 of the Present Invention) 4-proboxype/dyl alcohol in place of 4-1-gukboxy3-methoxybe/dyl alcohol in Production Example 5 The crude product obtained by performing the same operation using t7f (Q, 01 mol) t- was washed with xane to give the target compound 2.
．． If I got it.

Melting point 82.2-8a5℃ NMR (cDc4.δ, TMS); L 02
(3H, t, J=7Hz) 1.45-1.95 (2H,
m), t60(9H,5)A90(2H,t, J-
7Hz), A121 (2H, s) A87 (2H, d,
, T=8Hz), 7.30(2H, d.

J-8) 1z), 7.70 (IH, 5) 111 Production of 2-t-butyl-4-chloro-5-(4'-allyloxypenzyloxy)-5(2H)-pyridazinone (this Synthesis of Invention Compound 63) Perform the same operation using 1.7f (0.01 mol) of I/C4-allyloquinepenzyl alcohol instead of -1-propoquine-3-methquinepenzylanocol in Production Row 5. The crude product obtained was recrystallized from an n-hex/benzene mixed solvent to obtain the target compound 2.3f.

Melting point 91.2-94.2°C NMR (CDC4, δ;'['MS); 1.63 (9H
,s), 4.55 (28d, I=5Hz), 5
．． 26 (2L s), 5.15-5.64 (2H, m
), 5.78-6.44 (IH, m).

&97(2L (1,, T =9FIZ), 7.39
(2H, (1°J=9Hz), 7.79 (IH, s)
Manufacturing example day 2-t-butyl-4-chlor+s-(3'-butyl7
Production of penzyloxy-y)-5(2TI)-pyridazino/ (synthesis of the present compound black 74) 3-butquinbenzyl alcohol 1 in place of 4-1-propoxy-3-methquinopenzyl alcohol in Production Example 5 .8 f (α01 mol) f! : The crude product obtained by carrying out the same operation as above was recrystallized from a mixed solvent of n-hexa/benzene to obtain the target compound 2.6f. Melting point 77
．． 6-794℃ NMR (CDC4, δ, TMEI);
1-00 (3H, t, J=6Hz) 1.15~1
．． 94 (4H, m), 1.63C9H, a) A99 (
2H,t, ,T=6H2), 5.30(2H,5)
479-7.50 (4H, m), 7.76 (IH
,a)-7chlorohexyloxypenzyloxy7)-
Production of 3(2H)-pyridazinone (synthesis of compound point 146 of the present invention) 4-cyclohexyloxybenzyl alcohol 2.1r
(001 mol) t-N,N-dimethylformamide 20
55N sodium hydride (in mineral oil) (L5fi) was added to the nItK solution under stirring at 0°C. After stirring for 30 minutes at room temperature, 2-t-butyl-4,5-dichloro0-3 (2H) was added.
A solution of -pyridazino/2.2r ((101 mol) dissolved in N,N-dimethylformamide 10- was added dropwise and stirred overnight at room temperature. It was poured into ice water and extracted with benzene. The entire penozene layer was washed with water. After drying over anhydrous sodium sulfate, the solvent was distilled off under reduced pressure to obtain the crude product 14 f'fC.
Obtained. This was recrystallized from n-hexane to obtain the target compound 2.
I got Ot2.

Melting point 97.9-99.9°C NyiR (CDC4, δ, TMEI); 1-10
〜2.30(101(,m)1.60(9H,s),
390-450 (IH, m) 5.16 (2H, s),
483 (2H, d, J=9E1g) 7.24 (2H,
d, ,T-9Hz), 7.47(IH,8)m! !
41J1 Rainbow 2-t-butyl-4~ria o -5-[4'-(2'
-cyclohexenyloxy)pe/zyloxy1,5(2
a) Production of -pyridazino/ (synthesis of the compound of the present invention 150) K4-(2'-7 clohexenyl oxine)be/cyl alcohol 2+1f (101 The crude product fcn-hexaxabe/
Recrystallization from a mixed solvent of zene gave 2.7 tf of the target compound.

Melting point 11a5~121.0°C NMR (CDOL, δ, TMS); 1.40~
2!5 (6H, m) 160 (9H, B), 4.50~
alo (IH, m) 5.16 (2H, s), 5.84
(2H, bs) 484 (2H, d, , 7-9Hz)
, 7.24 (2H, d.

J = 9H2), 7.67 (IH, 8) 11'' Synthesis of compound At 61) 1.9 t (101 mol) of 4.5-dichloro-2-ethyl-5(2H)-pyridazinodi and 2.4 f (101 mol) of 4-octyloxybenzyl alcohol were combined with N,
The mixture was dissolved in 30y of N-dimethylformamide, and potassium hydroxide powder CL7f was added thereto, followed by stirring at room temperature overnight.

The reaction solution was poured into water and extracted with zeolite. The benzene layer was washed with an aqueous sodium hydroxide solution, washed with water, dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure.

The obtained crude product was washed with t-n-hexane and the target compound was processed 1ff! :Obtained. Melting point 8&0~87.0℃aMu(an
o4. δ, TMS); Q, 90 (LH, m),
1.08-2.10 (15H, m), α95 (2H,
t, J-6Hz) 420 (2H, q, J=7H1?
), α21(2H,8)α88(2H,d, ,T=
9Hz), 740 (2H, eL.

J = 9 Hz), 7.75 (IH, s) Production Example 12 Production of 2-t-butyl-4-chloro-5-(4'-tesyloxy-α-methylpe/dyloki)-5(2H)-pyridazinone (this Synthesis of Invention Compound 177) The same operation was carried out using VC4-f-y Luoquine-α-methylbenzyl alcohol 18F ([101 mol)] instead of 4-1-proboxyl-5-methoxybenzyl alcohol of Production Example 5. The obtained crude product was purified by column separation (silica gel; be/ze/ethyl acetate) to obtain the target compound (2.2 ft). Oil NMR (C!DC!4.δ,'I'MS)i α89
(3H, m), 1.10-2.10 (16H, m),
157 (9H, s), 1.66 (AH, d, J-
6Hz), 191 (2H, t, J-6Hz), 5. a
5 (IH, q, J=6Hz), α86 (2H, d,
J=9Hz), 7.26(2H,d, J=9Hg
), 7.55 (IH, 8) 1 seaweed - 13 2-t-butyl-4-riαcx -5-(4'-octylbenzyloxy)-3(2H)-pyridazinone production (the present compound 4193 Synthesis) A crude product obtained by carrying out the same operation using 4-octylbenzyl chloride (21X, containing 2-octylbenzyl chloride) 2.4f instead of 2-1-propylthiobenzyl chloride in Production Example 2. Wash the target compound 53F [isomer 2-t-butyl-4-
rioo-5-(2'-octylbenzyloxy)-5(
2H)-pyridazinone] was obtained. Oil NMR (cnc4.δ, TMI3); α87(AH
, m), t05~1.96 (12H, m), t61
(9H, θ), 2.49-182 (2H, m), 54
5 (2H, s), 7.02-7.48 (4H, ff1
), 7.71 (IL 8) When using the compounds of the present invention as agricultural and horticultural insecticides, acaricides, nematocides, fungicides, and insecticides for killing mites parasitic on animals, they are generally mixed with a suitable carrier 2, such as clay. , talc, be/tonite.

Solid carriers such as diatoms or water, alcohols (methanol, ethanol, etc.), aromatic hydrocarbons (benzene,
It can be applied in combination with liquid carriers such as toluene, xylene, etc.), fi-hydrogenated hydrogen chlorides, ethers, ketones, esters (ethyl acetate, etc.), and acid amides (dimethylformamide, etc.). Surfactant if desired.

Dispersants, WA clouding agents, penetrants, spreading agents, stabilizers, synergists, etc. are added to make solutions, emulsions, wettable powders, and powders.

It can be put to practical use in any dosage form such as granules, oils, and flowables. In addition, other types of herbicides and various insecticides may be used during formulation or spraying as necessary.

It may be applied in combination with fungicides, plant growth regulators, synergists, etc. The amount of the compound of the present invention to be applied depends on the application situation, application period,
There are differences depending on the application method, target pests, cultivated crops, etc., but in general, the amount of active ingredients is 1,005 to 100% per hectare.
Approximately #50 is appropriate.

Examples of formulations of bactericidal, insecticidal, acaricidal, nematicide, and animal-parasitic goo exterminators containing the compound of the present invention as an active ingredient are shown below, but the present invention is not limited to these. In addition,
In the following formulation examples, "parts" mean parts by weight.

Formulation example 1 Emulsion Compound of the present invention ・・・・・・・・・・・・・・・
・・・・・・・・・ 20 parts /
・・・・・・Song・−・・・・・・・−55fiKN-dimethylformamide ・・・・・・・・・・Concave・・・
20 Parts Ball 26BG......Song... 5 Parts (Mixture of nonionic surfactant and anionic surfactant: Toho Chemical Industry ■
Product name) Mix the above ingredients uniformly to make an emulsion. When used, the above emulsion is diluted 50 to 20,000 times and sprayed at an amount of active ingredient of 1,005 to 50 kg per hectare.

Formulation example 2 Wettable powder Compound of the present invention ・・・・・・・・・・・・・・・・
・・・・・・ Part 25 Sieglite PFP ・・・
・・・・・・・・・・・・・・・・-66fi (Mixture of kaolinite and sericite: Sieglite Industries ■Product name) Nluball 5059 ・・・・・・・・・・・・・・・
・・・・・・ 4 parts (Anionic surfactant: Toho Chemical Industry ■Product name) Carbrex Φ80 ・・・・・・・・・・・・・
・・・・・・・・・ 5 parts (white carbon:
Shionogi & Co. ■Product name) Calcium lignin sulfonate
・・・－・・・・・・・・・・・・ Two or more parts are uniformly mixed and pulverized to make an irrigation agent.

When used, the above-mentioned irrigation agent is diluted 50 to 20,000 times and sprayed so that the amount of active ingredient is n,oos to 50 yen per hectare.

Formulation example 3 Oil agent Compound of the present invention ・・・・・・・・・・・・・・・・
・・・−・・・ 10 parts methylsenorb ・・・
・・・・・・・・・・・・・・・・・・・・・ 90
Mix more than 10 parts uniformly to make an oil solution. When using, use the above oil in an amount of active ingredient or α005 to 5 per hectare.
Spread it so that it becomes 0 to 51.

Compound of the present invention °°°゛°°°°°°°°“−−−
−−−−−−°−xo section curvature, Kusu Φa o'=
``°°°°''−−−−−°−°−°−
- ・・・・・・・・・・・・－・・・・・・
・−・・・・ 95 parts phosphate a pill °゛°゛°°°°°゛°°°°°°°゛°°“−1
, 5 parts or more are uniformly mixed and ground to make a powder. When using the above powder, the amount of active ingredient is LL0 per hectare.
Spray to make it 0.05 to 50 Yu.

Formulation example 5 Granules Compound of the present invention ・・・・・・・・・・・・・・・・
・・・・・・・・・ 5th part bentonite ・・song・・・・song・・song・ 54th part tarri
...Men four songs... 40 parts Rikuni/
Calcium sulfonate - River -
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 at an amount of active ingredient of 0.000 s to 50 0.000 s per hectare.

Formulation Example 6 Flowable agent Compound of the present invention ・・・−・−・・・・・・・・・・・・
・・・・ 25th Division Ball 6556 ・・・・−
・・・・・・・・・・・・・・・・ IQt4 (Nonionic surfactant: Toho Chemical Industry ■Product name) Lunox 1
0000 ・・・・・・・・・・・・・・・・・・
... 1lL5 parts (lIi: ionic surfactant: Toho Chemical Industry ■Product name) 1X xanthan gum aqueous solution...
・・・・・・・・・・・・・・・−・ 20 parts (natural polymer) Water ・−・4 songs −・・
44.5 parts The above components except for the active ingredient (the compound of the present invention) are uniformly dissolved, and then the compound of the present invention is added and stirred well, followed by wet grinding in a sand mill to obtain a flowable agent. When using, the above 70 apples t-50 to 200
When diluted 00 times, the amount of active ingredient is C1 per hectare,
Spray at OO5-50kflC.

The compounds of the present invention are used for Hemiptera pests such as leafhoppers, Lepidoptera pests such as the diamondback moth, and Coleoptera pests.

It has excellent insecticidal power against sanitary pests such as Culex pipiens, and various mites that parasitize fruit trees and canola, such as the two-spotted spider mite and the Chikara/Zawa spider mite.

Mites that parasitize animals, such as the false red spider mite, the citrus spider mite, the red spider mite, etc., and the mites that parasitize animals, such as the American spider mite, Boophilus annulatus, Amplionma maculatum,
Ribicephalus appendiculatus, Futatogechi 1
It is also effective in controlling ticks, etc. In addition, various centiellae that parasitize fruit trees and cabbage, such as Nekopuse/Cheu,
It is also effective in controlling Negusarese/Cheu, Cystocentiera, etc. The major feature of the compound of the present invention is that in addition to the above-mentioned insecticidal and acaricidal effects, it is also effective in controlling diseases such as powdery mildew and downy mildew on fruit trees and cane rape, and is also highly safe for fish. . Therefore, the present invention
□The compound is an excellent agricultural chemical that can control pests and diseases in a wide range of fields without polluting water.

Livestock such as cows, horses, sheep, and pigs, 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.

Km Example 1 Insecticidal test against black leafhopper A rice leaf was immersed in an emulsion of the compound of the present invention at a concentration of 11,000 pp for about 10 seconds, and the grass blade was placed in a glass cylinder to kill adult black leafhopper that is resistant to organic/based insecticides. 10
Leave the down payment.

A nine-hole plastic lid was placed over the top. This cylinder is 2
The animals were housed in a constant temperature room 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 2.

Test Example 2 Contact Insecticidal Test against Nijeuyahonte/Tou: 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, and then placed in a petri dish.
Into this, 10 2nd instar larvae of the Japanese ladybug were released per petri dish.

The animals were placed in a constant temperature room at 25°C with a lid with a hole in them, and the mortality rate after 96 hours was calculated using the formula in F.

The test was conducted in two sections. The results are shown in Table 2.

Test Example 3 Acaricidal efficacy test against Kanzawa mites A leaf of I/Ge/ was cut into a circle with a diameter of 1.51 using a leaf punch and placed on a damp paper on a styrene cup with a diameter of 7 cWl. This was inoculated with 10 Zawa spider mite larvae per leaf. Half a day after inoculation, a chemical solution prepared by diluting the compound emulsion of the present invention with a spreading agent to a concentration of 11,000 pp was sprayed onto the styrofoam cup at a rate of 2 d using a rotating spray field. ,9
The mortality rate after 6 hours was calculated using the following formula.

The test was conducted in two sections.

The results are shown in Table 2.

Test Example 4 Nematicidal Efficacy Test against Necropseudocens Contaminated soil from Necropseunia was placed on a styrene cup with a diameter of 8 cm. The emulsion of the compound of the present invention is diluted with water to give 1
000 ppm concentration chemical solution all adjusted.

After adding all the spreading agent, 50 tons per styrene cup
The soil was irrigated at rt. After 48 hours, the indicator crop tomato bushes were transplanted. After 50 days of translocation, the roots of the tomato plants were piloted with water and an inspection for Nekop parasitism was conducted according to the following criteria.

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

Nekobu parasitism index O: No Nekobu is observed 1: Nekobu is slightly observed 2: Nekobu is moderately observed 5: Nekobu is observed in large numbers 1: Nekobu is observed in extremely large numbers Table 2 Table 3 Table 3 Test Example 5 Insecticidal test against black leafhopper (low concentration test) Same as Test Example 1. However, the concentrations of the nine compounds of the present invention and the control compound were set in four levels: 1000°, 500.100, and 10 ppm, respectively.

The results are shown in Table 4.

As a result, it can be seen that the compound of the present invention exhibits extremely strong insecticidal activity compared to a known control compound.

Table 4 Comparison compounds in Table 4 are European (Patent Publication No. 00)
The compound described in No. 88384 has the following structural formula.

Test Example 6 Disease Control Test on Chiequa cucumber (cultivar: Sagami Hanshiro) grown in pots for 2 weeks A chemical solution (100
0ppm) 2011t was sprayed per T-pot. The cucumbers were placed in a greenhouse for one day, and cucumbers and diseased bacteria (Pe)
eucloperono Bpora cuoensia
) spore suspension (15 spores per field at 150x)
All inoculations were carried out by spraying. Cucumbers and cucumbers inoculated with disease fungus spores were placed in a room at 25℃ and 100% relative humidity for 2 days.
The plants were left for 4 hours and then moved to a greenhouse to wait for the onset of disease. The degree of morbidity was investigated 7 days after inoculation. As a result, no symptoms were observed with the following compounds.

Compound of the present invention black 75,102,111,117°138
and 159° Test Example 7 Cucumber Powdery Mildew Control Test Using cucumbers (variety: Sagami Hanshiro) grown in pots for 2 weeks, a chemical solution prepared by adjusting the emulsion of 9 compounds of the present invention to a predetermined concentration at 1000 ppm t-
20-sprayed per pot. The cucumbers were kept in a greenhouse for one day, and the cucumber powdery mildew fungus (S erotheca
fuliginea) spore suspension (150x magnification)
The field of view was sprayed with 25 spores and exposed. The cucumbers were placed in a greenhouse at 25 to 30°C to wait for the onset of disease. The degree of morbidity was investigated 10 days after inoculation. the result.

No symptoms were observed with the following compounds.

Compound of the present invention 454,63,73,86,94゜111
．． 117.158, 1.39, 146, 155 and 1
62゜Test M Example B Fish toxicity test using Japanese medaka Diameter 201?
ffl, a 10 (7) high glass aquarium was filled with 24 water. A methanol solution of the compound of the present invention and a control compound was added to the solution to adjust the concentration of the test compound in water to 15 ppm.

This aquarium was kept in a constant temperature aquarium at 25°C, and 10 Japanese killifish were placed in it and observed over time.

Table 5 shows the survival rate after 48 hours.

Table 5 Comparative compounds A, B, C, and D in Table 5 are
This is the same as what is written below in the table.

Claims (3)

[Claims] (1) General formula (I): ▲Mathematical formulas, chemical formulas, tables, etc.▼(I) [In the formula, R is a linear or branched alkyl group having 2 to 6 carbon atoms, R^1 and R^ 2 each independently represents a hydrogen atom or a lower alkyl group, X represents a halogen atom,
R^3 is a hydrogen atom, a halogen atom, a lower alkyl group, or a lower alkoxy group, and R^4 is a linear or branched alkyl group having 3 to 12 carbon atoms, an alkenyl group, or a cycloalkyl group having 3 to 6 carbon atoms. or a cycloalkenyl group, Y represents -O-, -S-, ▲There are mathematical formulas, chemical formulas, tables, etc.▼, or ▲There are mathematical formulas, chemical formulas, tables, etc.▼, and m represents an integer from 1 to 4. , if m is 2 to 4, R^
3 may be the same or different. n represents 0 or 1. However, when n is 0, R^4 represents an alkyl group having 7 to 12 carbon atoms. ] A 3(2H)-pyridazinone derivative represented by: (2) General formula (II): ▲Mathematical formulas, chemical formulas, tables, etc.▼(II) [In the formula, R is a linear or branched alkyl group having 2 to 6 carbon atoms, X is a halogen atom, A represents a halogen atom or -OH. [In the formula, R^1 and R^2 each independently represent a hydrogen atom or a lower alkyl group, R^3 is a hydrogen atom, a halogen atom, a lower alkyl group, or a lower alkoxy group, R^
4 is a linear or branched alkyl group having 3 to 12 carbon atoms, an alkenyl group, a cycloalkyl group or cycloalkenyl group having 3 to 6 carbon atoms, and Y is -O-, -S-, ▲
There are mathematical formulas, chemical formulas, tables, etc. ▼ or ▲ There are mathematical formulas, chemical formulas, tables, etc. Good too. n represents 0 or 1. However, when n is 0, R^4
represents an alkyl group having 7 to 12 carbon atoms. B represents a halogen atom or -OH. ] General formula (I) characterized by reacting with a compound represented by: ▲There are mathematical formulas, chemical formulas, tables, etc.▼(I) R^1 and R^2 each independently represent a hydrogen atom or a lower alkyl group, X represents a halogen atom,
R^3 is a hydrogen atom, a halogen atom, a lower alkyl group, or a lower alkoxy group, and R^4 is a linear or branched alkyl group having 3 to 12 carbon atoms, an alkenyl group, or a cycloalkyl group having 3 to 6 carbon atoms. or a cycloalkenyl group, Y represents -O-, -S-, ▲There are mathematical formulas, chemical formulas, tables, etc.▼, or ▲There are mathematical formulas, chemical formulas, tables, etc.▼, and m represents an integer from 1 to 4. , if m is 2 to 4, R^
3 may be the same or different. n represents 0 or 1. However, when n is 0, R^4 represents an alkyl group having 7 to 12 carbon atoms. ] A method for producing a 3(2H)-pyridazinone derivative represented by: (3) General formula (I): ▲There are mathematical formulas, chemical formulas, tables, etc.▼(I) [In the formula, R is a linear or branched alkyl group having 2 to 6 carbon atoms, R^1 and R^ 2 each independently represents a hydrogen atom or a lower alkyl group, X represents a halogen atom,
R^3 is a hydrogen atom, a halogen atom, a lower alkyl group, or a lower alkoxy group, and R^4 is a linear or branched alkyl group having 3 to 12 carbon atoms, an alkenyl group, or a cycloalkyl group having 3 to 6 carbon atoms. or a cycloalkenyl group, Y represents -O-, -S-, ▲There are mathematical formulas, chemical formulas, tables, etc.▼, or ▲There are mathematical formulas, chemical formulas, tables, etc.▼, and m represents an integer from 1 to 4. , if m is 2 to 4, R^
3 may be the same or different. n represents 0 or 1. However, when n is 0, R^4 represents an alkyl group having 7 to 12 carbon atoms. ] 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.