JPS61268672A - Pyridazinone derivative, production thereof and insecticide, acaricide and germicide - Google Patents
Pyridazinone derivative, production thereof and insecticide, acaricide and germicideInfo
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- JPS61268672A JPS61268672A JP10962485A JP10962485A JPS61268672A JP S61268672 A JPS61268672 A JP S61268672A JP 10962485 A JP10962485 A JP 10962485A JP 10962485 A JP10962485 A JP 10962485A JP S61268672 A JPS61268672 A JP S61268672A
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Abstract
Description
【発明の詳細な説明】
本発明は、新規な5(2H1−ビリダジノン誘導体、そ
の製造法ならびに該誘導体を有効成分として含有する農
園芸用殺虫、殺ダニ、殺線虫、殺菌剤および動物に寄生
するダニの駆除剤に関するものである。ざらに詳しくは
。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.
一般式(■):
R8
〔式中、Rは炭素数1〜6の直鎖または分岐を有するア
ルキル基を、Xは酸素原子または硫黄原子を、R1およ
びR1はそれぞれ独立に水素原子または低級アルキル基
をs FLtおよびR1はそれぞれ独立に水素原子、
・・ロゲン原子、低級アルキル基、または4−メトキク
フェニル基を示すか。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?
もしくはR1とR4が一緒になって一つの結合を示す。Alternatively, R1 and R4 together represent one bond.
R9は炭素数1〜6の直鎖または分岐を有するアルキル
基あるいはアルクニル基または−ffc(Yは水素原子
、/・aゲン原子、炭素数1〜6の直鎖または分岐を有
するアルキル基、シククアルキル基、シクロアルキルオ
キシ基、炭素数1〜60直鎖または分岐を有するアルキ
ルオキシ基あるいはアルキルチオ基、炭素数1〜6の直
鎖または分岐を有するアルキルスルフィニル基あるいは
スルホニル基、低級I−クアルキル基。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.
低級ハロアルキルオキシ基、ノー1CIアルキルチオ基
、低級アルケニルオキ7基、トリメチルシリυ
(但し、2は]1aゲン原子、低級アルキル基。lower haloalkyloxy group, no 1CI alkylthio group, lower alkenyloxy 7 group, trimethylsilyl υ (however, 2 is] 1a gen atom, lower alkyl group).
低級アルコキシ基、低級ハロアルキル基あるいはニトロ
基を2mはOまたは1〜5の整数を示し、mが2〜5の
場合は2は同一でも互いに異なってもよい。) nは1
〜5の整数を示し。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.
nが2〜5の場合はYは同一でも異なってもよい)。八
はノ・ロゲ/原子を示す。〕で表される5+28)−ビ
リダジノン誘導体、その製造法ならびに該誘導体を有効
成分として含有する農園装用殺虫、殺ダニ、殺線虫、殺
菌剤および動物(寄生するダニの駆除剤に関するもので
ある。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.
本発明者らは先に一般式ぎ)で表される一部の5(2H
)−ピリダジノン誘導体が農園芸用殺虫、殺ダニ、殺線
虫、殺菌作用を有することを見出した。(ヨーロッパ特
許公開第0088584号および特開昭60−4175
号公報参照)
埒
〔式中2例えばぎはアルキル基 A/はハロゲン原子、
R6およびR2は水素原子または低級アルキル基、2は
11素原子もしくは硫費原子を示す。〕この公知の化合
物の最も大きな特徴の一つは312f()ピリダジノン
の5−位の2′原子にベンジル誘導体が結合しているこ
とにある。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.
また特公昭5B−7999号公報には
一般式LVI
で表される5(2H1−ピリダジノン誘導体として下記
の公知化合物Aが記載されている。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).
この公知化合物Aは5(2H1−ピリダジノンの2−位
の窒素原子にフェニル基が置換しており、また植物の発
育に影響を与える農薬として表記されており、農[H用
殺虫、役ダニ、殺線虫、殺菌剤および動物に寄生するダ
ニの駆除剤である本発明化金物とは全く異なるものであ
る。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.
本発明者らはその後もピリダジノン誘導体の研究を鋭意
行ってきた。その結果一般式([Il :c式中、
RI/i炭素数1〜6の直鎖または分岐を有するアルキ
ル基金、^はハaゲy/J[子を、x′は−gF(、/
saゲ7原子または−OHを示す。〕で表される化合物
と、一般式([[l :%式%()
〔式中# FLll R11188m R4およびR
6は前記と同じ意味f4−表し、x#はハロゲン原子、
−8日または一〇Hを示す。〕で表される化合物とを反
応させて励記一般式I11で表される本発明化合物を得
た。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.
さらに2本発明者らは、一般式(Ilで表される本発明
化合物が優れた殺虫、殺ダニ、殺線虫。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.
殺菌作用を有し、すでに例示した一般式話で表される公
知の化合物群と比べて活性が強くなっており、極めて低
い薬剤S1度で農園芸上有害な生物を有効に防除できる
ことを見いだし1本発明を完成した。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.
本発明に包含される化合物としては1例えば第1表およ
び第2表に示す化合物があげられる。Compounds included in the present invention include, for example, the compounds shown in Tables 1 and 2.
ただし、第1表および第2表の化合物はあくまで例示の
ためのものであって1本発明はこれらに限定されるもの
ではない。However, the compounds in Tables 1 and 2 are for illustration purposes only, and the present invention is not limited thereto.
〔ただし、第1表および第2表中、 Meはメチル基を
、 mtはエチル基を、 Proはプロピル基を。[However, in Tables 1 and 2, Me represents a methyl group, mt represents an ethyl group, and Pro represents a propyl group.
田はブチル基を、 Psαはペンチル基を、Hαはヘキ
シル基を、tはターシャリ−を、1はイソを。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はセカ/ダリーを示す。〕
なお1本発明に包含される化合物のなかで不斉炭素原子
を有する化合物の場合には、光学活性の(→体あるいは
←)体も含むものである。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.
第 1 表
次に本発明化合物の製造法について実施例を具体的にあ
げて説明するが9本発明はこれらのみに限定されるもの
ではない。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.
製造例1 2−1−ブチル−5−(2’−ブテニルチオ
)−4−クロロ−5j2F11−ビリダジノンの製造(
本発明化合物/f61の合成)2−t−ブチル−4−り
c2α−5−メルカプト−5t2f(l−ビリダジノン
2−2f(Q、01モル)およびクロチルクaリド1.
0f((LO11モル1fcN、N−ジメチルホルムア
ミド50idに溶かし無水炭酸ナトリウム1.5fを加
え60〜70℃で4時間攪拌した。この溶液を水に注ぎ
ベンゼ/で抽出した。ベンゼン層を無水硫酸ナトリウム
で乾燥し、減圧下で溶媒を留去して得られた結晶をべ/
ゼy −a−ヘキサン混合溶媒で再結晶して目的化合物
2.12を得た。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.
融点 72.0〜7SO℃
NMR(CDC4,J、 TMSI i 1.6519
H,sl、 1.7015H。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製造例24−フクロ−2−エチル−5−(5’−
メチル−2′−ブテニルオキシ+ −512H)−ピリ
ダジノ7の製造
(本発明化合物轟5の合成)
4−クロa−2−エチル−5−ヒドロキシ−5(2H1
−ピリダシ/y1.7rlCLO1モル)および1−ブ
ロモ−5−メチル−2−ブテン1.5rlα01モルl
’(u、N−ジメチルホルムアミド50ゴに溶かし無水
炭酸カリウム1.82を加え100〜120℃で5時間
攪拌した。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.
この溶液を水に注ぎベノゼ/で抽出した。ベンゼン層を
無水硫酸ナトリウムで乾燥し、減圧下で溶媒を留去して
得られた結晶をベンゼン−α−ヘキサンで再結晶して目
的化合物1.5fを得た。 融点 72.0〜7五〇℃
NMRl0DC4,δ、 TMi ; 1.55(5H
,t、 l−7E(zl。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。177 (6H, s l, 420 (2H, q, J
=7H6l.
4.74 +2H,d、 J−7E(zl、 S45
tIEI、 t。4.74 +2H, d, J-7E (zl, S45
tIEI, t.
、T−7Hz+、 7.72 (1H,sl−!1j」
−4−ブaモー2−エチル−5−(5’−フェニル−2
’−7”!ベニルオキシ)−5(2H1−ビリダジノン
の製造
(本発明化合物蔦24の合成)
4.5−ジブロモ−2−エチル−5(2H1−ビリダジ
ノン2.8rt(101モル)およびシンf ミルフル
:r−k 1−4 F (cLo 1 % ル) t−
Me N−ジメチルホルムアミド50−に溶かし水酸化
カリウムの扮末cLZfを加え室温で一晩攪拌した。こ
の溶液を水に注ぎペンゼ/で抽出した。, 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/.
べ/ゼ/層t−m水硫酸ナトリウムで乾燥し、減圧下で
溶媒を留去し、得られた結晶をKtO[(−水混合溶媒
で再結晶して目的化合物2.72を得た。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.
融点 11zO〜11a5℃
NMR(CDC4,δ、 TMSl i 1.34(5
H,t、 Jx7Hzl。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。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
製造例42−1−ブチル−4−りaa−5−11′−メ
チル−y−7エニルー1−プロペニルチオl −3(2
Hlピリダジノ/の製造 (本発明化合物洗29の合
成)2−t−ブチル−4−ククc!−5−メルカプト−
5(2HI−ビリダジノン2.2Ptα01モル)およ
び3−ククc2−5−メチル−1−7、=ルー1−プa
へ71.a f (cLo 11 %k l’(M、N
−ジメチルホルムアミド5aratK溶かし無水炭酸す
) IJウム1.4ft−加え70〜90℃で5時間攪
拌した。この溶液を水に注ぎベンゼンで抽出した。べ7
47層を無水硫酸ナトリウムで乾燥後、減圧下で溶媒を
留去し、得られた結晶ヲベンゼンー〇−へキサ/混合溶
媒で再結晶して目的化合物2.2fを得た。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.
融点 12&0〜12aO℃
NMR(CDC4,J、 TMSl i 1.60
(5H,d、 、T−7Hzl。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。1.6219H, s l, 4.50 (IH, q-d
, J-7Hz.
7Hzl、 6.1511H,d −d、 l−16日
ze 7Hz ’++468 (IH,d、 J=16
Hzl、 z57 (5[(、sl。7Hzl, 6.1511H,d -d, l-16thze 7Hz'++468 (IH,d, J=16
Hzl, z57 (5[(, sl.
7.77(IH,al
製造例5 2−1−ブチル−4−クロa−5−(5−、
a#−りαロフェニル)−1−プロペニルチオ)−3(
2H1−ピリダシツノの製造(本発明化合物ム48の合
成12−t−ブチル−4−りatx−5−メルカプ)−
3(2ii1−ビリダジノン2.2 f ([lG1モ
ル1およびP−りcIoシンナミルクロリド1.9t(
α01モルliN、M−ジメチルホルムアミド50dV
C溶かし無水炭酸カリウム1.82を加え70〜90℃
で3時間攪拌した。この溶液を水に注ぎベンゼンで抽出
した。べ747層を無水硫酸ナトリウムで乾燥後、減圧
下で溶媒を留去し、得られた結晶をべ/セン−n−ヘキ
サン混合溶媒で再結晶して目的化背物2−4fを得た。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.
融点 111.0〜112.0℃
N褪RtODOA、、δ、TM81 ; t65 (9
H−a l−五85(2H。Melting point 111.0-112.0°C N RtODOA, δ, TM81; t65 (9
H-a l-585 (2H.
d、、T−7日zl、&18(IH,t−d、Ix7H
z。d,, T-7th zl, &18 (IH, t-d, Ix7H
z.
16Hzl、 467(1電d、 J 薫16 HZ
)#7.27(4H,sl、 7.65(IH,sl製
造例62−1−ブチル−4−クロロ−5−〔5’ −(
5’、 4’−ジクロロフェニル)−1−プロペニル
チオ]−312H)−ビリダジノンの製造
(本発明化金物l6111の合成)
2−t−ブチル−4−りaロー5−メルカプト−3(2
H1−ビリダジノン2.2 t ((L 01モル1お
よび44−ジク(ffffシンナミルクロリド2.5
t ([lLo 105モル)′t−エタノール507
Vcmかし、水酸化カリウムの粉末I17 tf加え、
室温で5時間攪拌した。この溶液を水に注ぎベンゼンで
抽出した。ベンゼン層を無水硫酸ナトリウムで乾燥後、
減圧下に溶媒を留去した。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.
得られた結晶をペンゼア −11−ヘキサ/混合溶媒で
再結晶して目的化合物2.5fを得た。The obtained crystals were recrystallized from Penzea-11-hexa/mixed solvent to obtain the target compound 2.5f.
融点 12aO〜129. C1℃
NMR(ODO4,J、 TMt31 ;t64 (9
H,81,589(2H。Melting point 12aO~129. C1°C NMR (ODO4,J, TMt31;t64 (9
H, 81,589 (2H.
d、 、Tx7Hzl、 a25(1H,t−d、 J
=a7Hz。d, ,Tx7Hzl, a25(1H,t-d, J
=a7Hz.
16EIZl、 &681H1,d、 J=168zl
。16EIZl, &681H1,d, J=168zl
.
210〜7.604AH,m)、 7.70 (IH,
s 1製造例) 2−t−ブチル−4−クロロ−5−〔
y−(2−メチルフェニル)−2′−プロペニルチオ]
−3t2HI−ピリダジノ/の製造(本発明化金物ム1
23の合成)2−t−ブチル−4,5−ジクaa−5%
2El)−ピリダジノ7L2 f ((LO1モル)お
よびO−メチル7/ナミルメルカグタ/1.6F(CL
0105 モルl t−I II / −ル50 v
tに溶かし無水炭酸ナトリウム1.6ff加え一晩攪拌
した。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.
この溶液を水に注ぎベンゼンで抽出した。ベンゼン層を
無水硫酸ナトリウムで乾燥し、減圧下に溶媒を留去し得
られた結晶をべ/セン−n−”へキサ/で再結晶して目
的化合物2.52を得た。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.
融点 82−0〜84.0℃
NMR(ODO4,δ、’I’M81 i 1.62
(9H,5)、 2.29<LH,5)、 487 (
2H,d、 Js=7Hzl。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製造日82−1−ブチル−4−クロロ
−5−〔3’−(4’−メチルフェニル)−2′−プロ
ペニルオキシ]−5(2H1−ピリダジノ/の製造(本
発明化合物&128の合成)2−t−ブチル−4−クロ
ロ−5−ヒドロキ/−5(2H1−ビリダジノン2−O
t (α01モル)およびp−メチルシンナミルクロリ
ド1.8 f (cLo 1 [18%ルlをN、N−
ジメチルホルムアミド50.dに溶かし、無水炭酸カリ
ウム2.1ff:加え80〜100℃で4時間攪拌した
。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.
この溶液を水に注ぎベンゼンで抽出した。ベンゼン層を
水酸化ナトリウム水溶液で洗浄し、さらに水で洗浄した
後、無水硫酸す) IJウムで乾燥させた。減圧下にべ
/ゼアを留去し得られた結晶ヲペノゼンーα−ヘキサン
混金溶媒で再結し目的化合物2.2 ft−得た。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.
融点 157.0〜159.5℃
NMRIODO4,J、 TM9) ; 1.60 (
9H,81,L5213F(。Melting point 157.0-159.5℃ NMRIODO4, J, TM9); 1.60 (
9H, 81, L5213F (.
sl、 487 (2H,d、 、T=7E(zl、
6y18 (IH。sl, 487 (2H,d, ,T=7E(zl,
6y18 (IH.
t−d、 J−7E(z、 16Hzl、 1k681
1H,d。t-d, J-7E (z, 16Hzl, 1k681
1H,d.
J−16Hzl、7.(15(2H,d、、Ta58F
Izl。J-16Hzl, 7. (15(2H,d,,Ta58F
Izl.
7.2512EI、 d、 、T−8Hz l、 7
.69 (IEi、 81製造例92−1−ブチル−5
−(3’−(4’−を−ブチルフェニル)−1−メチル
−1−プクベニルオキシ〕−4−クロクー3(2H1−
ピリダジノンの製造
(本発明化合物4188の合成1
2−t−ブチル−4−クロo−5−ヒドaキシ−3t2
f(l−ピリダジノン2.0f(101モル)おjび1
−(p−t−7’チルフエニル)−3−クロル−2−メ
チル−1−プロペン2.5f(101モル)をへキサメ
チルホスホリックトリアミド50dに溶解し、無水炭酸
ナトリウム1.6tを加え、70〜100℃で5時間攪
拌した。この溶液を水に注ぎベンゼンで抽出した。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.
べ747層を水酸化ナトリウム水溶液で洗浄しさらに水
洗し、無水硫酸ナトリウムで乾燥させた。減圧下にベン
ゼ/を留去し得られた結晶をベンゼン−α−ヘキサンで
再結し目的化合物2、.5ft−得た。 融点 141
.7〜142.5ElMRIODC4,戊TM91
; 1.50(9H,sl、145 (9FI。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。gl, t97 (5H, sl, 475 (2L sl.
&52 (IEi、 s l、 7.2514Fi
、 ml、 7.68 (11i、51
製造例10 2−1−ブチル−5−1:5’−t4’−
t、−ブチルフェニル>−51−メチル−1−プロペニ
ルチオ〕−4−りaa−5(2H1−ピリダジノンの製
造
(本発明化合物ム198の合成)
2−t−ブチル−4−りaa−5−メルカプ)−5(2
H1−ピリダジノy2.2P(0,01モルlお!び1
− (p−t−7’チルフエニル)−5−りaa−1−
メチル−1−プロペy2−5f(101モル)fell
、N−ジメチルホルムアミド50−に溶かし、無水炭酸
カリウムty tt″加え室温で5時間攪拌した。この
溶液を水に注ぎベンゼンで抽出した。べ/ゲン層を無水
硫酸ナトリウムで乾燥し、減圧下に溶媒を留去すること
【より、目的化合物の粘稠液体2.89を得た。&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.久TM日1 ; 1.29(9
H,sl、 1.61 (9H。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,s l、 7.62
(I He 81製造例11 2−t−ブチル−4−
りaa−5−〔5’−<4’−ト17フルオαメチルフ
ェニル)−7−プロペニルチオ〕−5(2!11−ピリ
ダジノンの製造
(本発明化合物墓242の合成)
2−t−ブチル−4−りaa−5−メルカプ)−3(2
HI−ピリダジノンλ2F(α01モル1およびp−)
リフルオαメチルシ/す2ルクロリド2.5f(α01
G4モル)feM、M−ジメチルホルムアミド50dに
溶かし、無水炭酸カリウム1.6tを加え80〜100
℃で4時間攪拌した。この溶液を水に注ぎペンゼ/で抽
出した。ベンゼン層を無水硫酸ナトリウ、ムで乾燥後、
減圧下に溶媒を留去した。得られた結晶全ベンゼン−α
−へキサンで再結晶して目的化合物2.8fを得た。
融点 7&0〜77.0ElMR(ODOL、、δ、’
rM8); 1.63(9Ei、sl、 五85(
2El。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。(1, Jx7111z), 427 (1Fi, t-d,
Jx7Eiz.
16Hz)、1b70 (IH,d、l−16Hzl。16Hz), 1b70 (IH, d, l-16Hzl.
7.47 (4ff、 ml、 7.58 (HE、
al製造fi12 2−t−ブチル−4−りaa−
5−〔1′−メチル−ff−(4’−7エニルフエニル
1−2′−プロペニルチオ]−5(2E11−ピリダジ
ノンの製造
一不発明化合物ム265の合成)
2−t−ブチル−4−り四ロー5−メルカプト−5(2
H)−ピリダジノンλ2P(α01モル)および3−ク
ロロ−5−メチル−1−(P−フェニルフェニル)−1
−20ベア2.5f(10103モル)をlli、N−
ジメチルホルムアミド50dに溶かし、無水炭酸カリウ
ムt6Fを加え室温で5時間攪拌した。この溶液を水に
注ぎベンゼンで抽出した。べ747層を無水硫酸ナトリ
ウムで乾燥後、減圧下に溶媒を留去し得られた結晶をベ
ンゼン−α−ヘキサンで再結晶して目的化合物2.7
ff得た。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.
融点 12&0〜129.5℃
NMR((!D(1!4.δ、TMsl ; 1.
55(5H,d、J−7Hzl。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、 、T x7H*。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)製造例15
2−t−ブチル−4−クロロ−5−(3′−7エニルー
2′−プ h11ニルオキシ1−5(2H1−ビリダジ
ノンの製造
(本発明化合物4294の合成)
5−ヒトaキシ−1−フェニル−1−プロピンt5 t
(no 1モル)にN、N−ジメチルホルムアミド5
Gl1gを加え、ざらに0℃にて55N水素化ナトリウ
ムα45 Pi加え、1時間攪拌した。その後、2−1
−ブチル−45−ツクαロー5 (2E(l−ピリダジ
ノy2.2F(101モル)を加え室温で一晩攪拌した
。この溶液を水に注ぎぺ/ゼンで抽出した。べ/ゼンN
kt−無水硫酸ナトリウムで乾燥させ、減圧下に溶媒を
留去した。得られた結晶をべ/ゼ/−α−ヘキサンで再
結晶し目的化合物2.Otf得た。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.
融点 142−5〜1465℃
NMR(ODC4,4TMd) ; 1.62 (9F
I、 sl、 !i08 (2El、sl7.55 (
5H,bs、 l、 7.95 (IH,s1本発明化
合物を農園芸用殺虫、殺ダニ、殺線虫、殺菌剤および動
物に寄生するダニの駆除剤として使用するにあたっては
、一般には適当な担体1例えばクレー、タルク、ベント
ナイト。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.
珪藻上等の固体担体あるいは水、アルコール類(メタノ
ール、エタノール等)、芳香族灰化水素類(ぺ/ゼ/、
トルエン、キシレン等1. 塩素化炭化水素類、エーテ
ル類、ケトン類、エステル類(酢酸エチル等1.1アミ
ド類(ジメチルホルムアミド等)などの液体担体と混用
して適用することができ、所望により界面活性剤。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.
分散剤、懸濁剤、浸透剤、展着剤、安定剤などを添加し
、/W、剤、乳剤、水利剤、粉剤2粒剤。Dispersing agent, suspending agent, penetrating agent, spreading agent, stabilizer, etc. are added, /W, agent, emulsion, irrigation agent, 2 powder tablets.
フロワブル剤等任意の剤型にて実用に供することができ
る。また、必要に応じて製剤または散布時に他種の除草
剤、各種殺虫剤、殺菌剤、植物生長調節剤、共力剤など
と混合施用してもよい。本発明化金物の施用薬量は適用
場面、施用時期、施用方法、対象病害虫、栽培作物等に
より差異はあるが一般には有効成分量としてヘクタール
当たり(LOO5〜5〇−程度が適当である。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.
次に本発明化合物を有効成分とする殺菌、殺虫、殺ダニ
、殺線虫剤および動物に寄生するダニの駆除剤の配合例
を示すがこれらのみに限定されるものではない。なお、
以下の配合例において「部」は重量部を意味する。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.
配合例1 乳 剤
本発明化金物 ・・・・・・・・・・−川−・−
20部キクレ/ ・・川・・・・・・・・・・・・・
・・・ 55部N、N−ジメチルホルムアミド ・・・
・・・・・・・・・−・・・・・ 20 部ンルボー
ル2680 ・・・・・・・・・・・−・・・・
・・・・ 5 部(非イオン性界面活性剤とアニオ
ン性界面活性剤との混含物二東邦化学工業■商品名)
以上を均一に混合して乳剤とする。使用に際しては上記
乳剤’2so〜20000倍に希釈して有効成分量かへ
クタール当りlj (1005〜50−になるように散
布する。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.
配合例2 水和剤
本発明化合物 ・・・曲間−・・曲・・ 25
部ジークライトPFP ・−・・・・・・・・
・−・・・・−・・ 66 部(カオリナイトとセリ
サイトの混含物
:ジークライト工業■商品名)
7A、ボーh5Q59 ・曲間・・・曲間・
4 部(アニオン性界面活性剤
二東邦化学工業■商品名)
カープレックス舎80 ・・・・・・曲・−・・・
・曲 5 部(ホワイトカーボン:塩野義製薬■商
品名1リグニンスルホン酸カルシウム°”””””””
2 部以上を均一に混合粉砕して水利剤とす
る。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.
使用に際しては上記水利剤t−50〜20000倍に希
釈して有効成分量がヘクタール当たり[1G05〜50
−になるように散布する。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 -.
配合例3 油 剤
本発明化金物 ・・・・・・・・・・・・・・・
・−・・・・ 10 部メチルセロンルブ ・・・
・曲・・−・曲間・ 90 部以上を均一に混合して油
剤とする。使用に際しては上記油剤を有効成分量かへク
タール当たり[1005〜50ゆ【なるように散布する
。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こ盆」1」−粉剤
本発明化合物 ・・・・−・・・・・・・・・・−
・・ 五〇部カープレツクスナ80 ・−・・−・・
・・−・・・・・・・・・・−(L5g(ホワイトカー
ボン:塩野義製薬■商品名)クー し − ・・
・・・・・・・・・・・・・・・・・・・ 95部リ
す酸シイツブaビル ・・・・・・・・・・・・・・
・・・−・・ 1.5部以上を均一に混合粉砕して
粉剤とする。使用に際しては上記粉剤を有効成分量がへ
クタール当たり[1005〜50kgになるように散布
する。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.
配合例5 粒 剤
本発明化合物 5部ベントナイト
・・−・・・・・・・・・・・・・・・・・
54部タ ル り ・・
・・・・・・・・・・・・・・・・・・・ 40
部リグニ/スルホ/l!1!カルシウム ・・・曲面
・ 1 部以上を均一に混合粉砕して少量の水を
加えて攪拌混合し、押出式造粒機で造粒し、乾燥して粒
剤とする。使用に際しては上記粒剤を有効成分量かへク
タール当たりIIL005〜50嗜になるように散布す
る。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.
配合例670アプル剤
本発明化合物 ・−・・・・・・・・・・・・・
・・−・・ 25部′ ツルポール5555 、、
、、、−0−1−0−−−−− 10部(非イオン性
界面活性剤二東邦化学工業■商品名)ルノックス100
00 ・・・・・−・・・・・・・・・・・・・・
(15部(陰イオン界面活性剤:東邦化学工業■商
品名)1Xザンサ/ガム水溶液・・・・・・・・・・・
・・・・・・・・・・ 20部(天然高分子)
水 ・・・・・・・・・・・
・・・・・・・・・・ 445部有効分子を除く以上成
分を均一に溶解し、ついで本発明化合物を加えよく攪拌
した後、サンドミルにて湿式粉砕してフロアブル剤を得
る。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.
使用に際しては、上記フロアブル剤t−50〜2000
0倍に希釈して有効成分量かへクタール当たりQ、80
.5〜50に#になるように散布する。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.
本発明化合物は、ツマグロヨコバイ等の半翅目害虫、コ
ナガ等の鱗翅目害虫、N翅目害虫。The compound of the present invention is used for Hemiptera pests such as leafhopper, Lepidoptera pests such as diamondback moth, and Noptera pests.
アカイエカ等の衛生害虫に卓越した殺虫力を有するとと
もに、果樹および1菜に寄生する種々のダニ例えば、ナ
ミハダニ、カンザワノ1ダニ。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.
ニセナミハダニ、ミカンハダニ、リンゴハダニ等および
動物に寄生するダニ例えば、オウクマダニ、ブーフィラ
ス・アニエレイタス、アンブリオ/マ・マクレイタム、
リビセファラス・アペンディクラータス、フタトゲチマ
ダニ等の防除にも有効である。本発明化合物の大きな特
徴は上述した殺虫、殺ダニ作用に加えてウドノコ病、ベ
ト病等、果樹および1菜の病害防除にも有効なことであ
る。従って2本発明化金物は害虫および病害の防除を同
時に行い得る性質を有する優れた農薬である。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.
また、牛、馬、羊、豚などの家畜類、家禽類。Also, livestock such as cows, horses, sheep, and pigs, and poultry.
および犬、猫、うさぎなどの動物に寄生するダニの駆除
剤としても優れている。It is also an excellent exterminator for mites that infect animals such as dogs, cats, and rabbits.
以下の試験例において具体的に説明する。This will be specifically explained in the following test examples.
試験例1 ツマグロヨコバイに対する殺虫試験本発明化
合物の1000 ppm濃度の乳化液中にイネの蒐集を
約10秒間浸漬し、この蒐集をガラス円筒に入れ、有機
リン系殺虫剤に抵抗性を有するツマグclヨコバイ成虫
10頭を放ち、孔のあいたプラスチック製蓋をかぶせた
。この円筒を25℃恒温室に収容し、96時間経過後の
死去″st−下記の計算式から求めた。なお、試験は2
区制で行った。結果を第3表に示す。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.
!ニジェウヤホクテントウに対する接触性殺虫試験
本発明化合物の1000 ppcc+濃度の水乳化液中
にトマトの葉を約10秒間浸漬し、風乾後7ヤーレに入
れ、この中に二?エウヤホシテントウ2令幼虫をシャー
レ当たり10頭を成虫し、孔のあいた蓋をして25℃恒
温室に収容し、96時間経過後の死去率を下記の計算式
から求めた。! 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.
なお、試験Fi2区制で行った。結果を第3表に示す。The exam was conducted in two divisions. The results are shown in Table 3.
試験例3 カンザワハダニに対する殺ダニ効力試験
インゲンの葉をリーフパ/チを用いて径1.51の円形
に切り取り、径71のスチロールカップ上の湿った戸紙
上に置いた。これに力/ザワハダニ幼虫を1葉当たり1
0頭接種した。接種半日後に本発明化合物乳剤を展着剤
で11000pp!1度に希釈した薬液をスチロールカ
ップ当たり2ゴずつ回転式散布塔を用いて散布し。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.
96時間経過後の死去率を下記の計算式から求めた。な
お、試験は2区制で行った。The mortality rate after 96 hours was calculated using the following formula. The test was conducted in two sections.
結果を第3表に示す。The results are shown in Table 3.
第 3 表
試験例4 コナガに対する殺虫試験
本発明化合物の500 ppm濃度の水乳化液中にカフ
ランの葉を約10秒間浸漬し、風乾後シャーレに入れ、
この中にコナガ2令幼虫を放ち孔のあいた蓋をして25
℃の恒温室に収容し。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 ℃.
7日間経過後の死去率を調査した。その結果。The mortality rate after 7 days was investigated. the result.
以下の化合物は100Xの死去率を示した。The following compounds showed a mortality rate of 100X.
本発明化合物4413,55,101,122,123
゜128、155.156,182,185,184,
242および265゜
試験例5 ツマグロヨコバイに対する殺虫試験(低濃度
試験)
試験例1に準じた。ただし0本発明化合物および対照化
合物の濃度は、それぞれ1000・500.100およ
び10 ppmの4段階とした。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.
結果を第4表に示す。The results are shown in Table 4.
この結果0本発明化合物は公知の対照化金物と比較して
、極めて強い殺虫活性を呈することが判る。The results show that the compound of the present invention exhibits extremely strong insecticidal activity compared to known control metals.
試験例6 ニジュウヤホシテントウに対fる接触性試験
(低濃度試験)
試験例2に準じた。ただし1本発明化金物および対照化
金物の濃度は、それぞれ1000゜500.100およ
び10 ppmの4段階とした。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.
結果を第5表に示す。The results are shown in Table 5.
この結果1本発明化金物は公知の対照化合物と比較して
、極めて強い殺虫活性を呈することが判る。The results show that the metal product of the present invention exhibits extremely strong insecticidal activity compared to the known control compound.
第 4 表
a) %開昭60−4173g記載の化合物および請求
範囲の化合物
b) ヨーロッパ特許公開第0088584号に記載の
化合物および請求範囲の化合物
C)上段より1000.500,100および10 p
pm濃度でのそれぞれの死去率(4)
第 5 表
a)4?開昭60−4175に記載の化金物および請求
範囲の化金物
b)ヨーロッパ特許公開第0088584号に記載の化
合物および請求範囲の化合物
C) 上段より1000.500,100および10
ppm濃度でのそれぞれの死去率(8)
試験例フ キーウリベと病防除試験
2週間鉢で育成したキュウリ(品種:相模半白)′fc
用い9本発明化合物乳剤を所定濃度に調整した薬液(I
Q 00 ppm )を鉢当たり20d散布した。と
のキュウリを温室内に一昼装置きキュウリベと病菌(P
seudopironospora Oubeaaig
)の胞子懸濁液1150倍で1視野に15個の胞子)
を噴霧し接種を行った。キエウリベと病菌の胞子を接種
したキーウリを25℃、相対湿度100Xの部屋に24
時間置き、しかる後温室に移して発病を待った。接種7
日経過後に罹病度を調査した。その結果、以下の化合物
の場金に全く発病を認めなかった。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.
本発明化金物ム55,122,125,184゜242
および294゜
試験例日 キーウリうどんこ病防除試験2週間鉢で育成
したキーウリ(品種:相撲半白)を用い2本発明化合物
乳剤を所定濃度に調圧した薬液1000 ppmを鉢当
たり20d散布した。このキュウリを温室内に一昼装置
き、キ為ウリうどんこ病菌(13臨5rothsca
Fuliginsa )の胞子懸濁液(150倍で1視
野に25個の胞子1を噴霧し接種を行った。このキュウ
リを25〜5(Icの温室に置き発病を待った。接種1
0日経過後、に罹病&を調査した。その結果、以下の化
金物の場合に全く発病t−@めなかった。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.
本発明化付物洗122,125,188.199および
242゜
試験例9 イネいもち病防除効果試験
直径9a11のポットで育成した稲(日本晴5〜4葉期
)に9本発明化金物乳剤を1000 ppmの濃度に調
整した薬液を、スプレーガ/を用いてポット当た92Q
d散布した。散布翌日、イネいもち病菌(P5rriC
ularia 0r7Za砂1 f@子懸濁液(x15
0,40個/視野)を噴霧し、温度25℃。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.
湿度95N以上の接種箱に一昼夜入れた。後に室温に置
き、接種7日後に形成された病班数を測定し、下記の式
に従って防除価を算出した。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.
その結果、以下の化金物は100Xの防除価を示した。As a result, the following chemical compounds showed a control value of 100X.
本発明化金物朧40,48,122.125および16
5゜Inventive Kinmono Oboro 40, 48, 122, 125 and 16
5゜
Claims (3)
アルキル基を、Xは酸素原子または硫黄原子を、R_1
およびR_2はそれぞれ独立に水素原子または低級アル
キル基を、R_3およびR_4はそれぞれ独立に水素原
子、ハロゲン原子、低級アルキル基または4−メトキシ
フェニル基を示すか、またはR_3とR_4が一緒にな
って一つの結合を示す。R_3は炭素数1〜6の直鎖も
しくは分岐を有するアルキル基あるいはアルケニル基ま
たは▲数式、化学式、表等があります▼{Yは水素原子
、ハ ロゲン原子、炭素数1〜6の直鎖もしくは分岐を有する
アルキル基、シクロアルキル基、シクロアルキルオキシ
基、炭素数1〜6の直鎖もしくは分岐を有するアルキル
オキシ基あるいはアルキルチオ基、炭素数1〜6の直鎖
もしくは分岐を有するアルキルスルフィニル基あるいは
スルホニル基、低級ハロアルキル基、低級ハロアルキル
オキシ基、ハロアルキルチオ基、低級アルケニルオキシ
基、トリメチルシリル基、ジメチルアミノ基、ニトロ基
、▲数式、化学式、表等があります▼、▲数式、化学式
、表等があります▼、▲数式、化学式、表等があります
▼、▲数式、化学式、表等があります▼ (但し、Zはハロゲン原子、低級アルキル基、低級アル
コキシ基、低級ハロアルキル基あるいはニトロ基を、m
は0または1〜5の整数を示し、mが2〜5の場合はZ
は同一でも互いに異なってもよい。)nは1〜5の整数
を示し、nが2〜5の場合はYは同一でも異なってもよ
い。}。Aはハロゲン原子を示す。 〕で表される3(2H)−ピリダジノン誘導体。(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:
アルキル基を、Aはハロゲン原子を、X′は−SH、ハ
ロゲン原子または−OHを示す。〕で表される化合物と
、 一般式(III): ▲数式、化学式、表等があります▼(III) 〔式中、R_1およびR_2はそれぞれ独立に水素原子
または低級アルキル基を、R_3およびR_4はそれぞ
れ独立に水素原子、ハロゲン原子、低級アルキル基また
は4−メトキシフェニル基を示すか、またはR_3とR
_4が一緒になって一つの結合を示す。R_5は炭素数
1〜6の直鎖もしくは分岐を有するアルキル基あるいは
アルケニル基または▲数式、化学式、表等があります▼
{Yは水素原子、ハロゲ ン原子、炭素数1〜6の直鎖もしくは分岐を有するアル
キル基、シクロアルキル基、シクロアルキルオキシ基、
炭素数1〜6の直鎖もしくは分岐を有するアルキルオキ
シ基あるいはアルキルチオ基、炭素数1〜6の直鎖また
は分岐を有するアルキルスルフィニル基あるいはスルホ
ニル基、低級ハロアルキル基、低級ハロアルキルオキシ
基、ハロアルキルチオ基、低級アルケニルオキシ基、ト
リメチルシリル基、ジメチルアミノ基、ニトロ基、▲数
式、化学式、表等があります▼、▲数式、化学式、表等
があります▼、▲数式、化学式、表等があります▼、▲
数式、化学式、表等があります▼ (但レ、Zはハロゲン原子、低級アルキル基、低級アル
コキシ基、低級ハロアルキル基あるいはニトロ基を、m
は0または1〜5の整数を示し、mが2〜5の場合はZ
は同一でも互いに異なってもよい。)nは1〜5の整数
を示し、nが2〜5の場合はYは同一でも異なってもよ
い。}X″はハロゲン原子、−SHまたは−OHを示す
。〕で表される化合物とを反応させることを特徴とする
一般式( I ): ▲数式、化学式、表等があります▼( I ) 〔式中、Rは炭素数1〜6の直鎖または分岐を有するア
ルキル基を、Xは酸素原子または硫黄原子を、R_1お
よびR_2はそれぞれ独立に水素原子または低級アルキ
ル基を、R_3およびR_4はそれぞれ独立に水素原子
、ハロゲン原子、低級アルキル基または4−メトキシフ
ェニル基を示すか、もしくはR_3とR_4が一緒にな
って一つの結合を示す。R_5は炭素数1〜6の直鎖ま
たは分岐を有するアルキル基あるいはアルケニル基また
は▲数式、化学式、表等があります▼{Yは水素原子、
ハ ロゲン原子、炭素数1〜6の直鎖または分岐を有するア
ルキル基、シクロアルキル基、シクロアルキルオキシ基
、炭素数1〜6の直鎖または分岐を有するアルキルオキ
シ基あるいはアルキルチオ基、炭素数1〜6の直鎖また
は分岐を有するアルキルスルフィニル基あるいはスルホ
ニル基、低級ハロアルキル基、低級ハロアルキルオキシ
基、ハロアルキルチオ基、低級アルケニルオキシ基、ト
リメチルシリル基、ジメチルアミノ基、ニトロ基、▲数
式、化学式、表等があります▼、▲数式、化学式、表等
があります▼、▲数式、化学式、表等があります▼、▲
数式、化学式、表等があります▼ (但し、Zはハロゲン原子、低級アルキル基、低級アル
コキシ基、低級ハロアルキル基あるいはニトロ基を、m
は0または1〜5の整数を示し、mが2〜5の場合はZ
は同一でも互いに異なつてもよい。)nは1〜5の整数
を示し、nが2〜5の場合はYは同一でも異なってもよ
い}。Aはハロゲン原子を示す。〕で表される3(2H
)−ピリダジノン誘導体の製造法。(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.
ルキル基を、Xは酸素原子または硫黄原子を、R_1お
よびR_2はそれぞれ独立に水素原子または低級アルキ
ル基を、R_3およびR_4はそれぞれ独立に水素原子
、ハロゲン原子、低級アルキル基、または4−メトキシ
フェニル基を示すか、もしくはR_3とR_4が一緒に
なって一つの結合を示す。R_5は炭素数1〜6の直鎖
または分岐を有するアルキル基あるいはアルケニル基ま
たは▲数式、化学式、表等があります▼{Yは水素原子
、 ハロゲン原子、炭素数1〜6の直鎖または分岐を有する
アルキル基、シクロアルキル基、シクロアルキルオキシ
基、炭素数1〜6の直鎖または分岐を有するアルキルオ
キシ基あるいはアルキルチオ基、炭素数1〜6の直鎖ま
たは分岐を有するアルキルスルフィニル基あるいはスル
ホニル基、低級ハロアルキル基、低級ハロアルキルオキ
シ基、ハロアルキルチオ基、低級アルケニルオキシ基、
トリメチルシリル基、ジメチルアミノ基、ニトロ基、 ▲数式、化学式、表等があります▼、▲数式、化学式、
表等があります▼、▲数式、化学式、表等があります▼
、▲数式、化学式、表等があります▼ (但し、Zはハロゲン原子、低級アルキル基、低級アル
コキシ基、低級ハロアルキル基あるいはニトロ基を、m
は0または1〜5の整数を示し、mが2〜5の場合はZ
は同一でも互いに異なってもよい。)nは1〜5の整数
を示し、nが2〜5の場合はYは同一でも異なってもよ
い}。Aはハロゲン原子を示す。〕で表される3(2H
)−ピリダジノン誘導体の1種または2種以上を有効成
分として含有する農園芸用殺虫、殺ダニ、殺線虫、殺菌
剤および動物に寄生するダニの駆除剤。(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.
Priority Applications (10)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP10962485A JPS61268672A (en) | 1985-05-22 | 1985-05-22 | Pyridazinone derivative, production thereof and insecticide, acaricide and germicide |
DE8585114899T DE3578304D1 (en) | 1984-11-29 | 1985-11-25 | PYRIDAZINE DERIVATIVES, THEIR PRODUCTION AND INSECTICIDAL, ACARICIDIC, NEMATICIDIC, FUNGICIDIC COMPOSITIONS. |
EP85114899A EP0183212B1 (en) | 1984-11-29 | 1985-11-25 | Pyridazinone derivatives, preparation thereof, and insecticidal, acaricidal, nematicidal, fungicidal compositions |
EG755/85A EG17827A (en) | 1984-11-29 | 1985-11-27 | Pyridazinone derivatives,preparation thereof and insecticidal acaricidal nematicidal,fungicidal compositions |
AU50455/85A AU584369B2 (en) | 1984-11-29 | 1985-11-28 | Pyridazinone derivatives, preparation thereof, and insecticidal, acaricidal, nematicidal, fungicidal compositions |
ES549364A ES8703143A1 (en) | 1984-11-29 | 1985-11-28 | Pyridazinone derivatives, preparation thereof, and insecticidal, acaricidal, nematicidal, fungicidal compositions. |
CA000496387A CA1264161A (en) | 1984-11-29 | 1985-11-28 | Pyridazinone derivatives, preparation thereof, and insecticidal, acaricidal, nematicidal, fungicidal compositions |
CN198585108650A CN85108650A (en) | 1984-11-29 | 1985-11-28 | The preparation method of pyridazinone derivative, and insecticidal constituent kill acaricidal composition, and the nematicide composition kills (very) bacterium composition |
BR8505984A BR8505984A (en) | 1984-11-29 | 1985-11-29 | PRIDAZINONE DERIVATIVES, PREPARATION OF THESE AND INSECTICIDES, ACARICIDES, NEMATICIDES AND FUNGICIDES |
US07/127,518 US4874861A (en) | 1984-11-29 | 1987-11-30 | Pyridazinone derivatives, preparation thereof, and insecticidal, acaricidal, nematicidal, fungicidal compositions |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP10962485A JPS61268672A (en) | 1985-05-22 | 1985-05-22 | Pyridazinone derivative, production thereof and insecticide, acaricide and germicide |
Publications (1)
Publication Number | Publication Date |
---|---|
JPS61268672A true JPS61268672A (en) | 1986-11-28 |
Family
ID=14515001
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP10962485A Pending JPS61268672A (en) | 1984-11-29 | 1985-05-22 | Pyridazinone derivative, production thereof and insecticide, acaricide and germicide |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPS61268672A (en) |
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4837217A (en) * | 1985-04-19 | 1989-06-06 | Nissan Chemical Industries, Ltd. | Pyridazinone derivatives, preparation thereof, and insecticidal, acaricidal, nematicidal, fungicidal compositions |
US4874861A (en) * | 1984-11-29 | 1989-10-17 | Nissan Chemical Industries, Ltd. | Pyridazinone derivatives, preparation thereof, and insecticidal, acaricidal, nematicidal, fungicidal compositions |
US4877787A (en) * | 1983-06-23 | 1989-10-31 | Nissan Chemical Industries | Benzylthio pyridazinone derivatives, preparation thereof, and insecticidal acaricidal, fungicidal compositions |
US4906627A (en) * | 1986-02-08 | 1990-03-06 | Nissan Chemical Industries, Ltd. | Pyridazinone derivatives, and insecticidal, acaricidal and nematicidal compositions |
CN102675213A (en) * | 2012-05-28 | 2012-09-19 | 扬州鸿诚化工技术服务有限公司 | Pyridazinone-containing trifluorobutenyl derivatives and preparation method and applications thereof |
-
1985
- 1985-05-22 JP JP10962485A patent/JPS61268672A/en active Pending
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4877787A (en) * | 1983-06-23 | 1989-10-31 | Nissan Chemical Industries | Benzylthio pyridazinone derivatives, preparation thereof, and insecticidal acaricidal, fungicidal compositions |
US4874861A (en) * | 1984-11-29 | 1989-10-17 | Nissan Chemical Industries, Ltd. | Pyridazinone derivatives, preparation thereof, and insecticidal, acaricidal, nematicidal, fungicidal compositions |
US4837217A (en) * | 1985-04-19 | 1989-06-06 | Nissan Chemical Industries, Ltd. | Pyridazinone derivatives, preparation thereof, and insecticidal, acaricidal, nematicidal, fungicidal compositions |
US4906627A (en) * | 1986-02-08 | 1990-03-06 | Nissan Chemical Industries, Ltd. | Pyridazinone derivatives, and insecticidal, acaricidal and nematicidal compositions |
CN102675213A (en) * | 2012-05-28 | 2012-09-19 | 扬州鸿诚化工技术服务有限公司 | Pyridazinone-containing trifluorobutenyl derivatives and preparation method and applications thereof |
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