JPS61268672A - Pyridazinone derivative, production thereof and insecticide, acaricide and germicide - Google Patents

Abstract

NEW MATERIAL:A 3(2H)-pyridazinone derivative expressed by formula I [R represents 1-4C alkyl; X is O or S; R1 and R2 represent H or lower alkyl; R3 and R4 represent H, halogen atom, lower alkyl, 4-methylphenyl or R3 and R4 together link to form one bond; R5 represents 1-6C alkyl, alkenyl or formula II (Y represents H, halogen atom, etc.); n is 1-5 and Y may be same or different when n is 2-5; A is halogen atom]. EXAMPLE:2-t-Butyl-5-(2'-butenylthio)-4-chloro-3(2H)-pyridazinone. USE:Useful as an insecticide, acaricide, nematocide and germicide for agricultural and horticultural use and an expellent for mites parasitic on animals. PREPARATION:A compound expressed by formula III (X' represents -SH, halogen atom, etc.) is reacted with a compound expressed by formula IV (X'' represents halogen atom or -SH) to obtain the compound expressed by formula I.

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention provides novel 5(2H1-pyridazinone derivatives, their production methods, agricultural and horticultural insecticides, acaricides, nematocides, fungicides containing the derivatives as active ingredients, and parasitic agents for animals). This is about a tick exterminator.For more details.

General formula (■): R8 [In the formula, R is a linear or branched alkyl group having 1 to 6 carbon atoms, X is an oxygen atom or a sulfur atom, and R1 and R1 are each independently a hydrogen atom or a lower alkyl group. The group s FLt and R1 are each independently a hydrogen atom,
...Does it represent a rogen atom, a lower alkyl group, or a 4-methoxyphenyl group?

Alternatively, R1 and R4 together represent one bond.

R9 is a straight-chain or branched alkyl group having 1 to 6 carbon atoms, an alknyl group, or -ffc (Y is a hydrogen atom, /.agen atom, a straight-chain or branched alkyl group having 1 to 6 carbon atoms, cycloalkyl a cycloalkyloxy group, a straight-chain or branched alkyloxy group or alkylthio group having 1 to 60 carbon atoms, a straight-chain or branched alkylsulfinyl group or sulfonyl group having 1 to 6 carbon atoms, and a lower I-qualkyl group.

lower haloalkyloxy group, no 1CI alkylthio group, lower alkenyloxy 7 group, trimethylsilyl υ (however, 2 is] 1a gen atom, lower alkyl group).

In a lower alkoxy group, a lower haloalkyl group, or a nitro group, 2m represents O or an integer of 1 to 5, and when m is 2 to 5, 2 may be the same or different from each other. ) n is 1
Indicates an integer between ~5.

When n is 2 to 5, Y may be the same or different). Eight represents no loge/atom. ] The present invention relates to a 5+28)-pyridazinone derivative represented by the following formula, a method for producing the same, and a pesticide for agricultural use, an acaricide, a nematocide, a fungicide, and an agent for controlling animal (parasitic mites) containing the derivative as an active ingredient.

The present inventors previously demonstrated that some 5 (2H) represented by the general formula
)-pyridazinone derivatives have been found to have insecticidal, acaricidal, nematicidal, and bactericidal effects for agricultural and horticultural purposes. (European Patent Publication No. 0088584 and JP-A-60-4175
(Refer to the publication No.)
R6 and R2 represent a hydrogen atom or a lower alkyl group, and 2 represents an 11-element atom or a sulfur atom. ] One of the most significant features of this known compound is that a benzyl derivative is bonded to the 2' atom at the 5-position of 312f()pyridazinone.

Furthermore, Japanese Patent Publication No. 5B-7999 describes the following known compound A as a 5(2H1-pyridazinone derivative represented by the general formula LVI).

This known compound A has a phenyl group substituted on the nitrogen atom at the 2-position of 5(2H1-pyridazinone), and is described as a pesticide that affects plant growth. This invention is completely different from the metal product of the present invention, which is a nematocide, a fungicide, and an exterminator for mites parasitic on animals.

Since then, the present inventors have continued to conduct intensive research on pyridazinone derivatives. As a result, the general formula ([Il: in the formula c,
RI/i is a linear or branched alkyl group having 1 to 6 carbon atoms, ^ is bald y/J[child, x' is -gF(,/
Indicates 7 atoms or -OH. ], and a compound represented by the general formula ([[l:% formula%() [in the formula #FLll R11188m R4 and R
6 represents the same meaning as above f4-, x# is a halogen atom,
- indicates 8 days or 10 hours. ] to obtain the compound of the present invention represented by the general formula I11.

Furthermore, the present inventors found that the compound of the present invention represented by the general formula (Il) is an excellent insecticide, acaricide, and nematicide.

It has been found that it has a bactericidal effect and is more active than the known compound group represented by the general formula mentioned above, and that it is possible to effectively control organisms harmful to agriculture and horticulture with an extremely low level of chemical S1. The invention has been completed.

Compounds included in the present invention include, for example, the compounds shown in Tables 1 and 2.

However, the compounds in Tables 1 and 2 are for illustration purposes only, and the present invention is not limited thereto.

[However, in Tables 1 and 2, Me represents a methyl group, mt represents an ethyl group, and Pro represents a propyl group.

ta stands for butyl group, Psa stands for pentyl group, Hα stands for hexyl group, t stands for tertiary, and 1 stands for iso.

8 indicates second/dally. ] Among the compounds included in the present invention, in the case of a compound having an asymmetric carbon atom, the optically active (→ or ←) form is also included.

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

Production Example 1 Production of 2-1-butyl-5-(2'-butenylthio)-4-chloro-5j2F11-pyridazinone (
Synthesis of Compound of the Present Invention/f61) 2-t-Butyl-4-lyc2α-5-mercapto-5t2f (l-pyridazinone 2-2f (Q, 01 mol) and crotyl chloride 1.
0f((LO11mol 1fcN, dissolved in 50id of N-dimethylformamide, added 1.5f of anhydrous sodium carbonate, and stirred at 60-70°C for 4 hours.The solution was poured into water and extracted with benzene/.The benzene layer was dissolved in anhydrous sodium sulfate. The crystals obtained by distilling off the solvent under reduced pressure are
The target compound 2.12 was obtained by recrystallization with a mixed solvent of zey-a-hexane.

Melting point 72.0-7SO℃ NMR (CDC4, J, TMSI i 1.6519
H, sl, 1.7015H.

d, :f-7)1z), i63 (28,a, J=
7H2IS65 (2H, ml, 7.57 (IL
s 1 Production Example 24-Fuclo-2-ethyl-5-(5'-
Production of methyl-2'-butenyloxy + -512H)-pyridazino 7 (synthesis of the present compound Todoroki 5) 4-Chloa-2-ethyl-5-hydroxy-5 (2H1
-pyridacy/y1.7rlCLO1 mol) and 1-bromo-5-methyl-2-butene1.5rlα01 moll
'(u, 1.82 g of anhydrous potassium carbonate was dissolved in 50 g of N-dimethylformamide, and the mixture was stirred at 100 to 120° C. for 5 hours.

This solution was poured into water and extracted with benoze/. The benzene layer was dried over anhydrous sodium sulfate, the solvent was distilled off under reduced pressure, and the obtained crystals were recrystallized from benzene-α-hexane to obtain the target compound 1.5f. Melting point 72.0-750℃ NMRl0DC4,δ, TMi; 1.55 (5H
,t, l-7E(zl.

177 (6H, s l, 420 (2H, q, J
=7H6l.

4.74 +2H, d, J-7E (zl, S45
tIEI, t.

, T-7Hz+, 7.72 (1H, sl-!1j"
-4-b-a-2-ethyl-5-(5'-phenyl-2
'-7"!benyloxy)-5(2H1-pyridazinone (synthesis of the present compound Tsuta 24) : r-k 1-4 F (cLo 1% le) t-
To the mixture was added potassium hydroxide powder cLZf dissolved in Me N-dimethylformamide 50-, and the mixture was stirred overnight at room temperature. This solution was poured into water and extracted with Penze/.

The mixture was dried over t-m sodium sulfate, the solvent was distilled off under reduced pressure, and the obtained crystals were recrystallized from a mixed solvent of KtO[(-water) to obtain the target compound 2.72.

Melting point 11zO~11a5℃ NMR (CDC4, δ, TMSl i 1.34 (5
H,t, Jx7Hzl.

4.21 (2He qe J-7E(z l -4-
95 (2H-d-J=7E(zl, &50 (IFI
, t-d, :f-7H2゜16Fizl, &79
(IH,d, ,T=16E(Zl.

7.3515f(, s l, 7.75 (IH, sl
Production Example 42-1-Butyl-4-riaa-5-11'-methyl-y-7enyl-1-propenylthio l-3(2
Production of Hlpyridazino/ (Synthesis of Compound 29 of the Invention) 2-t-butyl-4-kuku c! -5-Mercapto-
5 (2HI-pyridazinone 2.2Ptα01 mol) and 3-kucc2-5-methyl-1-7, = loop 1-p a
71. a f (cLo 11 %k l'(M, N
1.4 ft. of dimethylformamide was dissolved in anhydrous carbonic acid, and the mixture was stirred at 70 to 90° C. for 5 hours. This solution was poured into water and extracted with benzene. Be7
After drying layer 47 over anhydrous sodium sulfate, the solvent was distilled off under reduced pressure, and the resulting crystals were recrystallized from a benzene-0-hex/mixed solvent to obtain the target compound 2.2f.

Melting point 12&0~12aO℃ NMR (CDC4,J, TMSl i 1.60
(5H, d, , T-7Hzl.

1.6219H, s l, 4.50 (IH, q-d
, J-7Hz.

7Hzl, 6.1511H,d -d, l-16thze 7Hz'++468 (IH,d, J=16
Hzl, z57 (5[(, sl.

7.77 (IH, al Production Example 5 2-1-butyl-4-chloroa-5-(5-,
a#- α-Lophenyl)-1-propenylthio)-3(
Production of 2H1-pyridazine (synthesis of compound 48 of the present invention 12-t-butyl-4-riatx-5-mercap)-
3 (2ii1-pyridazinone 2.2 f ([lG1 mol 1 and P-lycIo cinnamyl chloride 1.9 t (
α01 mol liN, M-dimethylformamide 50 dV
Dissolve C and add 1.82% of anhydrous potassium carbonate to 70-90℃
The mixture was stirred for 3 hours. This solution was poured into water and extracted with benzene. After drying the Be 747 layer over anhydrous sodium sulfate, the solvent was distilled off under reduced pressure, and the obtained crystals were recrystallized from a Be/cene-n-hexane mixed solvent to obtain the desired product 2-4f.

Melting point 111.0-112.0°C N RtODOA, δ, TM81; t65 (9
H-a l-585 (2H.

d,, T-7th zl, &18 (IH, t-d, Ix7H
z.

16Hzl, 467(1dend, J Kaoru 16Hz
) #7.27 (4H, sl, 7.65 (IH, sl) Production Example 62-1-Butyl-4-chloro-5-[5'-(
Production of 5',4'-dichlorophenyl)-1-propenylthio]-312H)-pyridazinone (synthesis of present invention metal compound 16111) 2-t-butyl-4-ri-5-mercapto-3(2
H1-pyridazinone 2.2 t ((L 01 mol 1 and 44-dic(ffff cinnamyl chloride 2.5
t ([lLo 105 mol)'t-ethanol 507
Vcm, add potassium hydroxide powder I17 tf,
The mixture was stirred at room temperature for 5 hours. This solution was poured into water and extracted with benzene. After drying the benzene layer with anhydrous sodium sulfate,
The solvent was distilled off under reduced pressure.

The obtained crystals were recrystallized from Penzea-11-hexa/mixed solvent to obtain the target compound 2.5f.

Melting point 12aO~129. C1°C NMR (ODO4,J, TMt31;t64 (9
H, 81,589 (2H.

d, ,Tx7Hzl, a25(1H,t-d, J
=a7Hz.

16EIZl, &681H1,d, J=168zl
.

210-7.604AH, m), 7.70 (IH,
s 1 Production Example) 2-t-butyl-4-chloro-5-[
y-(2-methylphenyl)-2'-propenylthio]
-Production of 3t2HI-pyridazino/(inventive metal product M1)
Synthesis of 23) 2-t-butyl-4,5-dicaa-5%
2El)-pyridazino7L2 f ((1 mol of LO) and O-methyl 7/namylmercaguta/1.6F(CL
0105 mol l t-I II / -le 50 v
1.6 ff of anhydrous sodium carbonate was added to the solution and stirred overnight.

This solution was poured into water and extracted with benzene. The benzene layer was dried over anhydrous sodium sulfate, the solvent was distilled off under reduced pressure, and the resulting crystals were recrystallized from benzene-n-''hexa/ to obtain the target compound 2.52.

Melting point 82-0~84.0℃ NMR (ODO4, δ, 'I'M81 i 1.62
(9H, 5), 2.29<LH, 5), 487 (
2H,d, Js=7Hzl.

lb 10 (1f(-t -d-J-7HZ, 16
Hz I #489 (I H,d, , T=16H
2), 7.10-7.50 (4H, ml, 7.70
(IH, sll Manufacture date 82-1-butyl-4-chloro-5-[3'-(4'-methylphenyl)-2'-propenyloxy]-5 (2H1-pyridazino/manufacture of the present compound &128 synthesis) 2-t-butyl-4-chloro-5-hydroxy/-5 (2H1-pyridazinone 2-O
t (α01 mol) and p-methylcinnamyl chloride 1.8 f (cLo 1 [18% mol) N, N-
Dimethylformamide 50. d, and 2.1 ff of anhydrous potassium carbonate was added thereto, followed by stirring at 80 to 100°C for 4 hours.

This solution was poured into water and extracted with benzene. The benzene layer was washed with an aqueous sodium hydroxide solution, further washed with water, and then dried over anhydrous sulfuric acid. Be/zea was distilled off under reduced pressure, and the resulting crystals were recrystallized in a penosene-α-hexane mixed metal solvent to obtain 2.2 ft of the target compound.

Melting point 157.0-159.5℃ NMRIODO4, J, TM9); 1.60 (
9H, 81, L5213F (.

sl, 487 (2H,d, ,T=7E(zl,
6y18 (IH.

t-d, J-7E (z, 16Hzl, 1k681
1H,d.

J-16Hzl, 7. (15(2H,d,,Ta58F
Izl.

7.2512EI, d, , T-8Hz l, 7
．． 69 (IEi, 81 Production Example 92-1-Butyl-5
-(3'-(4'-butylphenyl)-1-methyl-1-pcubenyloxy)-4-crocou3(2H1-
Production of pyridazinone (synthesis of the present compound 4188 1 2-t-butyl-4-chloroo-5-hydroxy-3t2
f (l-pyridazinone 2.0f (101 mol) and 1
-(pt-7'tylphenyl)-3-chloro-2-methyl-1-propene 2.5f (101 mol) was dissolved in hexamethylphosphoric triamide 50d, and anhydrous sodium carbonate 1.6t was added. , and stirred at 70-100°C for 5 hours. This solution was poured into water and extracted with benzene.

The 747 layer was washed with an aqueous sodium hydroxide solution, further washed with water, and dried over anhydrous sodium sulfate. Benzene/ was distilled off under reduced pressure, and the resulting crystals were re-crystallized with benzene-α-hexane to obtain target compounds 2, . 5ft-obtained. Melting point 141
．． 7~142.5ElMRIODC4, 戊TM91
; 1.50 (9H, sl, 145 (9FI.

gl, t97 (5H, sl, 475 (2L sl.

&52 (IEi, s l, 7.2514Fi
, ml, 7.68 (11i, 51 Production Example 10 2-1-butyl-5-1:5'-t4'-
t,-Butylphenyl>-51-methyl-1-propenylthio]-4-aa-5 (2H1-pyridazinone production (synthesis of the present compound 198) 2-t-butyl-4-aa-5 - Mercap) -5 (2
H1-pyridazinoy2.2P (0.01 mol l and 1
- (pt-7'tylphenyl)-5-riaa-1-
Methyl-1-propey2-5f (101 mol) fell
, dissolved in N-dimethylformamide 50-, anhydrous potassium carbonate was added, and the mixture was stirred at room temperature for 5 hours. The solution was poured into water and extracted with benzene. The benzene layer was dried over anhydrous sodium sulfate, and the solution was stirred at room temperature for 5 hours. By distilling off the solvent, a viscous liquid 2.8% of the target compound was obtained.

NMR (CD04.KuTM day 1; 1.29 (9
H, sl, 1.61 (9H.

s I= 2.12 (5H-s L 1B G
(2H-d-1!7Hz),! x81 (IH,t,,
7-7Hzl, Z28 (4H, sl, 7.62
(I He 81 Production Example 11 2-t-butyl-4-
2-t-butyl -4-riaa-5-mercap)-3(2
HI-pyridazinone λ2F (α01 mol 1 and p-)
Refluor α methyl chloride 2.5f (α01
G4 mol) feM, M-Dissolved in 50 d of dimethylformamide, added 1.6 t of anhydrous potassium carbonate to 80-100
The mixture was stirred at ℃ for 4 hours. This solution was poured into water and extracted with Penze/. After drying the benzene layer with anhydrous sodium sulfate,
The solvent was distilled off under reduced pressure. Obtained crystal total benzene-α
Recrystallization from -hexane gave the target compound 2.8f.
Melting point 7&0~77.0ElMR(ODOL,,δ,'
rM8); 1.63 (9Ei, sl, 585 (
2El.

(1, Jx7111z), 427 (1Fi, t-d,
Jx7Eiz.

16Hz), 1b70 (IH, d, l-16Hzl.

7.47 (4ff, ml, 7.58 (HE,
al production fi12 2-t-butyl-4-riaa-
5-[1'-Methyl-ff-(4'-7enylphenyl 1-2'-propenylthio]-5 (Production of 2E11-pyridazinone - Synthesis of uninvented compound Mu265) 2-t-Butyl-4-ri Four-row 5-Mercapto-5 (2
H)-pyridazinone λ2P (α01 mol) and 3-chloro-5-methyl-1-(P-phenylphenyl)-1
-20 bear 2.5f (10103 mol) lli, N-
The mixture was dissolved in 50 d of dimethylformamide, added with anhydrous potassium carbonate t6F, and stirred at room temperature for 5 hours. This solution was poured into water and extracted with benzene. After drying the Be747 layer over anhydrous sodium sulfate, the solvent was distilled off under reduced pressure, and the resulting crystals were recrystallized from benzene-α-hexane to obtain the target compound 2.7.
I got ff.

Melting point 12&0-129.5°C NMR ((!D(1!4.δ, TMsl; 1.
55 (5H, d, J-7Hzl.

1.59 (98,8), 4.24 (I El,
4-a, ,Tx7H*.

7Hz), 6.14 (IH, d - d, J
-16Hz, 71izl&62 (IEI, d
, J-16Hz +, 7.20~7.65 (
9H, ml, 7.69 (IH, s) Production example 15
2-t-butyl-4-chloro-5-(3'-7enyl-2'-p h11nyloxy1-5 (2H1-Production of pyridazinone (synthesis of the present compound 4294) 5-hydroxy-1-phenyl -1-propyne t5 t
(no 1 mol) to N,N-dimethylformamide 5
1 g of Gl was added, and 55N sodium hydride α45 Pi was added to the colander at 0°C, followed by stirring for 1 hour. After that, 2-1
-Butyl-45-tsukuro5 (2E(l-pyridazinoy2.2F (101 mol)) was added and stirred overnight at room temperature.The solution was poured into water and extracted with Be/Zen.
It was dried over kt-anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained crystals were recrystallized from be/ze/-α-hexane to obtain the target compound 2. I got OTF.

Melting point 142-5~1465℃ NMR (ODC4,4TMd); 1.62 (9F
I, sl,! i08 (2El, sl7.55 (
5H, bs, l, 7.95 (IH, s1) When using the compounds of the present invention as agricultural and horticultural insecticides, acaricides, nematocides, fungicides, and insecticidal agents for mites parasitic on animals, generally appropriate Carrier 1 For example clay, talc, bentonite.

Solid carriers such as diatoms or water, alcohols (methanol, ethanol, etc.), aromatic hydrogen ash (pe/ze/,
Toluene, xylene, etc.1. It can be applied in combination with a liquid carrier such as chlorinated hydrocarbons, ethers, ketones, esters (ethyl acetate, etc.), 1.1 amides (dimethylformamide, etc.), and optionally a surfactant.

Dispersing agent, suspending agent, penetrating agent, spreading agent, stabilizer, etc. are added, /W, agent, emulsion, irrigation agent, 2 powder tablets.

It can be put to practical use in any form such as a flowable agent. Further, if necessary, other herbicides, various insecticides, fungicides, plant growth regulators, synergists, etc. may be mixed and applied during formulation or spraying. The amount of the chemical compound of the present invention to be applied varies depending on the application situation, application time, application method, target pests, cultivated crops, etc., but in general, the appropriate amount of active ingredient per hectare (LOO 5 to 50) is appropriate.

Examples of formulations of bactericidal, insecticidal, acaricidal, nematicide, and animal-parasitic mite 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 Inventive metal material ・・・・・・・・−Kawa−・−
Part 20 Kikure/ ・・River・・・・・・・・・・・・・
... 55 parts N,N-dimethylformamide ...
・・・・・・・・・－・・・・・・ 20 Division Ball 2680 ・・・・・・・・・・・・・・・・・・
... 5 parts (mixture of nonionic surfactant and anionic surfactant 2 Toho Chemical Industry ■ trade name) The above is mixed uniformly to form an emulsion. When used, the above emulsion is diluted 2so to 20,000 times and sprayed so that the amount of active ingredient is lj (1005 to 50) per hectare.

Formulation Example 2 Wettable powder Compound of the present invention... Between songs... Song... 25
Part Sieglite PFP ・・・・・・・・・・・・・・・
・−・・−・・ 66 parts (mixture of kaolinite and sericite: Sieglite Kogyo ■Product name) 7A, Boh5Q59 ・Between songs...Between songs・
Part 4 (Anionic surfactant 2 Toho Chemical Industry■Product name) Carplex Sha80...Song...
・Song part 5 (White Carbon: Shionogi & Co., Ltd. ■Product name 1 Calcium lignin sulfonate °”””””””
Mix and grind 2 or more parts uniformly to make an irrigation agent.

When using, dilute the above irrigation agent t-50 to 20,000 times so that the amount of active ingredient per hectare [1G05-50
Spread it so that -.

Formulation example 3 Oil agent Inventive metal material ・・・・・・・・・・・・・・・
・－・・・・ 10 parts Methylseronlube ・・・
・Songs...between songs・Mix 90 parts or more evenly to make an oil solution. When used, the above-mentioned oil agent is sprayed at an amount of 1,005 to 50 Yu per hectare of active ingredient.

J Kobon"1" - Powder Compound of the present invention ・・・・−・・・・・・・・・・・・−
・・ 50 parts car plexusna 80 ・−・・−・・
・・・・・・・・・・・・・(L5g (White Carbon: Shionogi & Co., Ltd. ■Product name) Coo - ・・
・・・・・・・・・・・・・・・・・・・・・ 95 parts lithic acid shiitsubu a building ・・・・・・・・・・・・・・・・・・
...-- 1.5 parts or more are uniformly mixed and pulverized to form a powder. When used, the above-mentioned powder is spread so that the amount of active ingredient is 1005 to 50 kg per hectare.

Formulation example 5 Granules Compound of the present invention 5 parts Bentonite ・・・・・・・・・・・・・・・・・・・・・
Part 54...
・・・・・・・・・・・・・・・・・・・・・ 40
Part Ligni/Sulho/l! 1! Calcium: Curved surface - 1 or more parts are uniformly mixed and pulverized, a small amount of water is added, the mixture is stirred, and the mixture is granulated using an extrusion granulator and dried to form granules. When used, the above-mentioned granules are dispersed at an amount of IIL005 to 50 per hectare of the active ingredient.

Formulation example 670 Apple preparation Compound of the present invention ・・・・・・・・・・・・・・・・・・
・・・-・・ Part 25' Tsurupol 5555 ,,
,,, -0-1-0------ 10 parts (Nonionic surfactant 2 Toho Chemical Industry ■ Trade name) Lunox 100
00 ・・・・・・－・・・・・・・・・・・・・・・
(15 parts (anionic surfactant: Toho Chemical Industry ■Product name) 1X xantha/gum aqueous solution...
・・・・・・・・・・・・ 20 parts (natural polymer) Water ・・・・・・・・・・・・
445 parts The above components except for the effective molecules 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 flowable agent t-50~2000
The amount of active ingredient when diluted to 0 times is Q per hectare, 80
．． Spray to a #5 to #50.

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

It has excellent insecticidal power against sanitary pests such as Culex mosquito, and also various mites that parasitize fruit trees and vegetables, such as the two-spotted spider mite and the Kanzawano 1 mite.

False spider mite, citrus spider mite, apple spider mite, etc., and mites parasitic on animals, such as the African spider mite, Boophilus aniereitus, Amblyo/ma maculatum,
It is also effective in controlling Ribicephalus appendiculatus, Phyllis ticks, etc. 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 vegetables, such as powdery mildew and downy mildew. Therefore, the two invented metal products are excellent agricultural chemicals that have the property of simultaneously controlling pests and diseases.

Also, 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.

Test Example 1 Insecticidal test against black leafhopper A rice collection was immersed in an emulsion of the compound of the present invention at a concentration of 1000 ppm for about 10 seconds, and the rice collection was placed in a glass cylinder. Ten adult insects were released and covered with a perforated plastic lid. This cylinder was placed in a constant temperature room at 25°C, and death after 96 hours was calculated from the following formula.
It was done by ward system. The results are shown in Table 3.

! Contact Insecticidal Test against Yellow Lady Beetle Tomato leaves were immersed in a water emulsion of the compound of the present invention at a concentration of 1000 ppcc for about 10 seconds, air-dried, placed in a 7-year container, and placed in a 7-year container. Ten adult 2nd instar ladybird larvae per Petri dish were placed in a thermostatic chamber at 25° C. with a perforated lid, and the mortality rate after 96 hours was calculated using the following formula.

The exam was conducted in two divisions. The results are shown in Table 3.

Test Example 3 Acaricidal efficacy test against Kanzawa spider mites A green bean leaf was cut into a circle with a diameter of 1.51 mm using a leaf pouch and placed on a damp paper on a styrene cup with a diameter of 71 mm. Add power to this / Zawa spider mite larva per leaf 1
0 animals were vaccinated. Half a day after inoculation, apply the compound emulsion of the present invention as a spreading agent at 11,000 pp! Spray the diluted chemical solution two times per styrene cup using a rotary spray tower.

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.

Table 3 Test Example 4 Insecticidal test against diamondback moth Kaflan leaves were immersed in a water emulsion containing the compound of the present invention at a concentration of 500 ppm for about 10 seconds, air-dried, and then placed in a petri dish.
Place the 2nd instar larvae of the diamondback moth into this, cover the hole with a lid, and
Housed in a constant temperature room at ℃.

The mortality rate after 7 days was investigated. the result.

The following compounds showed a mortality rate of 100X.

Compounds of the present invention 4413,55,101,122,123
゜128, 155.156, 182, 185, 184,
242 and 265° Test Example 5 Insecticidal test against leafhopper (low concentration test) Same as Test Example 1. However, the concentrations of the compound 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.

The results show that the compound of the present invention exhibits extremely strong insecticidal activity compared to known control metals.

Test Example 6 Contact test against Japanese lady beetle (low concentration test) Test example 2 was followed. However, the concentrations of the present invention metal material and the control metal material were set in four levels: 1000°, 500.100 ppm, and 10 ppm, respectively.

The results are shown in Table 5.

The results show that the metal product of the present invention exhibits extremely strong insecticidal activity compared to the known control compound.

Table 4 a) Compounds described in % Open Showa 60-4173g and claimed compounds b) Compounds described in European Patent Publication No. 0088584 and claimed compounds C) 1000.500, 100 and 10 p from the top row
Respective mortality rates at pm concentrations (4) Table 5 a) 4? The metal compound described in 1988-4175 and the claimed metal compound b) The compound described in European Patent Publication No. 0088584 and the claimed compound C) 1000, 500, 100 and 10 from the top row
Mortality rate at each ppm concentration (8) Test example: Cucumber cucumber grown in pots for 2 weeks (variety: Sagami Hanshiro)'fc
A drug solution (I
Q 00 ppm) was sprayed for 20 d per pot. The cucumbers were placed in a greenhouse for one day, and the cucumbers and diseased bacteria (P
seudopironospora Oubeaaig
15 spores per field of view at 1150x magnification
Inoculation was carried out by spraying. Chie cucurbita and Chie cucumber inoculated with disease fungus spores were placed in a room at 25℃ and relative humidity 100X for 24 hours.
After waiting for some time, they were moved to a greenhouse and waited for the disease to develop. Inoculation 7
The degree of morbidity was investigated after a day had passed. As a result, no disease onset was observed in the following compounds.

Inventive metal material 55, 122, 125, 184° 242
and 294° Test Example Day Kikucurbita Powdery Mildew Control Test Using Kikucurbita (variety: Sumo Hanshiro) grown in pots for 2 weeks, 1000 ppm of a chemical solution prepared by adjusting the concentration of two compound emulsions of the present invention to a predetermined concentration was sprayed for 20 d per pot. The cucumbers were placed in a greenhouse for one day and infected with the fungus Powdery Mildew (135 rothsca).
The cucumbers were inoculated by spraying a spore suspension (25 spores 1 in one field of view at 150x magnification) of P. fuliginsa).The cucumbers were placed in a greenhouse at 25-5 (Ic) to wait for the onset of disease.Inoculation 1
After 0 days, the disease was investigated. As a result, no disease occurred in the case of the following metal compounds.

Test Example 9 Rice blast control effect test of the present invention Jukusai 122, 125, 188, 199 and 242°. 9 Inventive metal emulsions were applied to rice (Nipponbare 5-4 leaf stage) grown in pots with a diameter of 9a11 at 1,000 ml. Apply the chemical solution adjusted to a ppm concentration to the pot using a sprayer/92Q.
d was sprayed. The day after spraying, rice blast fungus (P5rriC)
ularia 0r7Za sand 1 f@ child suspension (x15
0.40 pieces/field of view) at a temperature of 25°C.

The seeds were placed in an inoculation box with a humidity of 95N or higher overnight. The plants were then placed at room temperature, the number of diseased spots formed 7 days after inoculation was measured, and the control value was calculated according to the following formula.

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

Inventive Kinmono Oboro 40, 48, 122, 125 and 16
5゜

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 1 to 6 carbon atoms, and X is an oxygen atom or sulfur. Atom, R_1
and R_2 each independently represent a hydrogen atom or a lower alkyl group, R_3 and R_4 each independently represent a hydrogen atom, a halogen atom, a lower alkyl group, or a 4-methoxyphenyl group, or R_3 and R_4 together represent a shows two bonds. R_3 is a straight chain or branched alkyl group or alkenyl group having 1 to 6 carbon atoms, or ▲ Numerical formula, chemical formula, table, etc. ▼ {Y is a hydrogen atom, a halogen atom, a straight chain or branched chain having 1 to 6 carbon atoms an alkyl group, a cycloalkyl group, a cycloalkyloxy group, a straight-chain or branched alkyloxy group or alkylthio group having 1 to 6 carbon atoms, a straight-chain or branched alkylsulfinyl group or sulfonyl group having 1 to 6 carbon atoms; , lower haloalkyl group, lower haloalkyloxy group, haloalkylthio group, lower alkenyloxy group, trimethylsilyl group, dimethylamino group, nitro group, ▲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. ▼ (However, Z is a halogen atom, lower alkyl group, lower alkoxy group, lower haloalkyl group, or nitro group,
indicates 0 or an integer of 1 to 5, and if m is 2 to 5, Z
may be the same or different from each other. )n represents an integer of 1 to 5, and when n is 2 to 5, Y may be the same or different. }. A represents a halogen atom. ] 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 1 to 6 carbon atoms, A is a halogen atom, X' represents -SH, a halogen atom or -OH. [In the formula, R_1 and R_2 are each independently a hydrogen atom or a lower alkyl group, and R_3 and R_4 are Each independently represents a hydrogen atom, a halogen atom, a lower alkyl group, or a 4-methoxyphenyl group, or R_3 and R
_4 together indicate a bond. R_5 is a linear or branched alkyl group or alkenyl group with 1 to 6 carbon atoms, or ▲a mathematical formula, chemical formula, table, etc.▼
{Y is a hydrogen atom, a halogen atom, a linear or branched alkyl group having 1 to 6 carbon atoms, a cycloalkyl group, a cycloalkyloxy group,
Straight chain or branched alkyloxy group or alkylthio group having 1 to 6 carbon atoms, straight chain or branched alkylsulfinyl group or sulfonyl group having 1 to 6 carbon atoms, lower haloalkyl group, lower haloalkyloxy group, haloalkylthio group , lower alkenyloxy group, trimethylsilyl group, dimethylamino group, nitro group, ▲ 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.▼ (However, Z is a halogen atom, lower alkyl group, lower alkoxy group, lower haloalkyl group, or nitro group, m
indicates 0 or an integer of 1 to 5, and if m is 2 to 5, Z
may be the same or different from each other. )n represents an integer of 1 to 5, and when n is 2 to 5, Y may be the same or different. }X'' represents a halogen atom, -SH or -OH.] General formula (I): ▲There are mathematical formulas, chemical formulas, tables, etc.▼(I) [ In the formula, R is a linear or branched alkyl group having 1 to 6 carbon atoms, X is an oxygen atom or a sulfur atom, R_1 and R_2 are each independently a hydrogen atom or a lower alkyl group, and R_3 and R_4 are each They independently represent a hydrogen atom, a halogen atom, a lower alkyl group, or a 4-methoxyphenyl group, or R_3 and R_4 together represent one bond. R_5 has a linear or branched chain with 1 to 6 carbon atoms. Alkyl group or alkenyl group or ▲Mathematical formula, chemical formula, table, etc.▼{Y is a hydrogen atom,
Halogen atom, straight chain or branched alkyl group having 1 to 6 carbon atoms, cycloalkyl group, cycloalkyloxy group, straight chain or branched alkyloxy group or alkylthio group having 1 to 6 carbon atoms, 1 to 6 carbon atoms 6 linear or branched alkylsulfinyl group or sulfonyl group, lower haloalkyl group, lower haloalkyloxy group, haloalkylthio group, lower alkenyloxy group, trimethylsilyl group, dimethylamino group, nitro group, ▲mathematical formula, chemical formula, table, etc. There are ▼, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼, ▲
There are mathematical formulas, chemical formulas, tables, etc.▼ (However, Z is a halogen atom, lower alkyl group, lower alkoxy group, lower haloalkyl group, or nitro group, m
indicates 0 or an integer of 1 to 5, and if m is 2 to 5, Z
may be the same or different. ) n represents an integer of 1 to 5, and when n is 2 to 5, Y may be the same or different}. A represents a halogen atom. ] 3(2H
)-Production method of pyridazinone derivative. (3) General formula (I): ▲Mathematical formulas, chemical formulas, tables, etc.▼(I) [In the formula, R is a straight chain or branched alkyl group having 1 to 6 carbon atoms, and X is an oxygen atom or sulfur. R_1 and R_2 each independently represent a hydrogen atom or a lower alkyl group, R_3 and R_4 each independently represent a hydrogen atom, a halogen atom, a lower alkyl group, or a 4-methoxyphenyl group, or R_3 and R_4 each independently represent a hydrogen atom or a lower alkyl group; Together they show a union. R_5 is a straight chain or branched alkyl group or alkenyl group having 1 to 6 carbon atoms, or ▲ Numerical formula, chemical formula, table, etc. ▼ {Y is a hydrogen atom, a halogen atom, a straight chain or branched chain having 1 to 6 carbon atoms alkyl group, cycloalkyl group, cycloalkyloxy group, straight chain or branched alkyloxy group or alkylthio group having 1 to 6 carbon atoms, straight chain or branched alkylsulfinyl group or sulfonyl group having 1 to 6 carbon atoms , lower haloalkyl group, lower haloalkyloxy group, haloalkylthio group, lower alkenyloxy group,
Trimethylsilyl group, dimethylamino group, nitro group, ▲Mathematical formulas, chemical formulas, tables, etc.▼, ▲Mathematical formulas, chemical formulas,
There are tables, etc. ▼, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼
, ▲Mathematical formulas, chemical formulas, tables, etc.▼ (However, Z is a halogen atom, lower alkyl group, lower alkoxy group, lower haloalkyl group, or nitro group, m
indicates 0 or an integer of 1 to 5, and if m is 2 to 5, Z
may be the same or different from each other. ) n represents an integer of 1 to 5, and when n is 2 to 5, Y may be the same or different}. A represents a halogen atom. ] 3(2H
) - Agricultural and horticultural insecticides, acaricides, nematocides, fungicides, and agents for killing mites parasitic on animals, which contain one or more pyridazinone derivatives as an active ingredient.