JP2001072512A - Plant disease-controlling agent composition - Google Patents

Plant disease-controlling agent composition

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Publication number
JP2001072512A
JP2001072512A JP24940099A JP24940099A JP2001072512A JP 2001072512 A JP2001072512 A JP 2001072512A JP 24940099 A JP24940099 A JP 24940099A JP 24940099 A JP24940099 A JP 24940099A JP 2001072512 A JP2001072512 A JP 2001072512A
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Japan
Prior art keywords
group
carbon atoms
compound
atom
component
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JP24940099A
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Japanese (ja)
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JP4090639B2 (en
Inventor
Yuji Yanase
勇次 柳瀬
Yukihiro Yoshikawa
幸宏 吉川
Junro Kishi
淳郎 貴志
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Mitsui Chemicals Inc
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Mitsui Chemicals Inc
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Abstract

PROBLEM TO BE SOLVED: To obtain the subject composition capable of exhibiting synergistically improved effect against the infection of powdery mildew by including a specific substituted thiophene derivative and a triazol-based compound. SOLUTION: This composition contains at least two kinds of active ingredients of (A) a substituted thiophene derivative represented by formula I [Q is H, methyl, trifluoromethyl or the like; R is a 3-12C alkyl, a 3-12C halogenoalkyl or the like; Ar is a group of formula II (R1 is trifluoromethyl, difluoromethyl or the like; R2 is H, methyl, trifluoromethyl or the like; n is 0-2) or the like], and (B) at least one compound of a triazol-based compound, an imidazole-based compound, a morpholine-based compound, a benzimidazole- based compound (preferably thiophanate-methyl), an anilinopyrimidine-based compound (preferably mepanipyrim), an acrylate-based compound, iminoctadine albesilate and polyoxin.

Description

【発明の詳細な説明】DETAILED DESCRIPTION OF THE INVENTION

【0001】[0001]

【発明の属する技術分野】本発明は、少なくとも2種の
有効成分を含有し、うどんこ病の感染に対して相乗的に
増強された効果を有する植物病害防除剤組成物である。
更に詳しくは、有効成分の一方が植物病害防除作用を示
す置換チオフェン誘導体であり、他方がトリアゾール系
化合物、イミダゾール系化合物、モルフォリン系化合
物、ベンズイミダゾール系化合物、アニリノピリミジン
系化合物、アクリレート系化合物、イミノクタジン・ア
ルベシル酸塩、ポリオキシンから選ばれる化合物のうち
の少なくとも一つを含有する殺菌剤組成物に関する。
TECHNICAL FIELD The present invention relates to a plant disease controlling composition containing at least two active ingredients and having a synergistically enhanced effect on powdery mildew infection.
More specifically, one of the active ingredients is a substituted thiophene derivative showing a plant disease controlling action, and the other is a triazole compound, an imidazole compound, a morpholine compound, a benzimidazole compound, an anilinopyrimidine compound, an acrylate compound. And a fungicidal composition containing at least one compound selected from iminoctadine albesilate and polyoxin.

【0002】[0002]

【従来の技術】近年開発された選択的作用を示す殺菌剤
は、それまで使用されてきた非選択的な殺菌剤と異なり
低薬量で安定した効果を示すが、繰り返し使用した場合
に薬剤耐性が出現し、効力の低下を来す恐れがある。そ
の対策として、予防的剤との混合、作用機作の異なる薬
剤との混合、あるいは薬剤自身の使用回数の制限も行わ
れているとともに、新たな薬剤の開発が期待されてい
る。
2. Description of the Related Art A disinfectant having a selective action developed in recent years shows a stable effect at a low dose unlike a non-selective disinfectant which has been used up to that time. May appear, resulting in reduced efficacy. As a countermeasure, mixing with a prophylactic agent, mixing with a drug having a different mechanism of action, or limiting the number of times the drug itself is used, and the development of a new drug is expected.

【0003】特開平9−235282号公報(欧州特許
公開第737682号公報)には、成分Iで表される新
たな置換チオフェン誘導体が種々の病害に対して殺菌効
果を有することが知られている。この化合物は、灰色か
び病、うどんこ病を含む種々の病害の感染に対して予防
的および治療的な防除効果を示す。
[0003] Japanese Patent Application Laid-Open No. 9-235282 (EP-A-737682) discloses that a new substituted thiophene derivative represented by the component I has a bactericidal effect against various diseases. . This compound has a prophylactic and therapeutic control effect against infection of various diseases including gray mold and powdery mildew.

【0004】一方、成分IIはトリアゾール系化合物、
イミダゾール系化合物、モルフォリン系化合物、ベンズ
イミダゾール系化合物、アニリノピリミジン系化合物、
アクリレート系化合物、イミノクタジン・アルベシル酸
塩、ポリオキシンから選ばれる公知の化合物であり、以
下に一般名[“商品名(英名)”、頁]で示し、頁と
は、[ザ ペスチサイド マニュアル(The Pes
ticide Manual)、第11版、The B
ritish Crop ProtectionCou
ncil、1997年]の記載頁を示す。
On the other hand, component II is a triazole compound,
Imidazole compounds, morpholine compounds, benzimidazole compounds, anilinopyrimidine compounds,
It is a known compound selected from acrylate compounds, iminoctadine albesylate, and polyoxin, and has the following general name [“trade name (English name)”, page], and the page refers to [The Pesticide Manual (The Pesside).
ticide Manual), 11th edition, The B
write Crop ProtectionCou
ncil, 1997].

【0005】A.トリアゾール系化合物 1.プロピコナゾール[“プロピコナゾール(Til
t)”、第1030〜1032頁] 2.トリアジメノール[“バイタン(Bayta
n)”、第1218〜1220頁] 3.ペンコナゾール[“トパス”(Topas)、第9
33〜935頁] 4.テブコナゾール[“フォリキュラー(Folicu
r)”、第1144〜1146頁] 5.フルシラゾール[“ナスター(Nustar)”、
第1003〜1004頁] 6.ジニコナゾール[“スミ−8(Sumi−8)”、
第421〜422頁] 7.ブロムコナゾール[“グラニット(Grani
t)”、第152〜153頁] 8.エポキシコナゾール[“オープス(Opus)”、
第79〜80頁] 9.ジフェノコナゾール[“スコア(Score)”、
第389〜391頁] 10.シプロコナゾール[“アルト(Alto)”、第
1003〜1004頁] 11.メトコナゾール[“カランバ(Caramb
a)”、第803〜804頁] 12.ミクロブタニル[“ミクロブタニル(Myclo
butanil)”、第854〜856頁] 13.フェンブコナゾール[“インダー(Inda
r)”、第508〜509頁] 14.ヘキサコナゾール[“アンビル(Anvi
l)”、第674〜675頁] 15.フルキンコナゾール[“カステラン(Caste
llan)”、第588〜589頁] 16.ビテルタノール[“バイコール(Bayco
r)”、第131〜133頁]
A. Triazole-based compound Propiconazole ["Propiconazole (Til
t) ", pp. 1030-1032] 2. Triadimenol [" Baytan (Bayta
n) ", pp. 1218-1220] 3. Penconazole [" Topas ", ninth
33-935] 4. Tebuconazole [“Folicu
r) ", pp. 1144-1146] 5. Flusilazole [" Nustar ",
1003 to 1004] 6. Diniconazole [“Sumi-8”,
421-422] 7. Bromconazole [Grani
t) ", pp. 152-153] 8. Epoxyconazole [" Opus ",
79-80] 9. Difenoconazole [“Score”,
389-391] 10. 10. Cyproconazole [“Alto”, pp. 1003-1004] Metoconazole ["Caramba"
a) ", pp. 803-804] 12. Microbutanyl [" Microbutanyl (Myclo
butanil) ", pages 854-856] 13. Fenbuconazole [" Inda
r) ", pp. 508-509] 14. Hexaconazole [" Anvil
1) ", pp. 674-675] 15. Flukinconazole [" Castelane "
llan) ", pp. 588-589] 16. Bitertanol [" Bayco "
r) ", pp. 131-133]

【0006】B.イミダゾール系化合物 1.イマザリル[“フンガフロール(Fungaflo
r)”、第691〜693頁] 2.プロクロラツ[“スポルタック(Sporta
k)”、第1000〜1002頁] 3.トリフルミゾール[“トリフミン(Trifmin
e)”、第1245〜1246頁]
B. Imidazole compounds 1. Imazalil ["Fungaflor
r) ”, pp. 691-693] 2. Prochlorats [“ Sporta (Sporta)
k) ", pp. 1000-1002] 3. Triflumizole [" Trifmin
e) ", pp. 1245-1246]

【0007】C.モルフォリン系化合物 1.フェンプロピモルフ[“コーベル(Corbe
l)”、第528〜529頁] 2.トリデモルフ[“カリキシン(Calixi
n)”、第1242〜1243頁] 3.ドデモルフ[“メルタトックス(Meltato
x)”、第449〜451頁]
C. Morpholine-based compounds Fenpropimorph [Corbe
l) ", pp. 528-529] 2. Tridemorph [" Calixi "
n) ", pp. 1242-1243] 3. Dodemorph [" Meltatox "
x) ", pp. 449-451]

【0008】D.ベンズイミダゾール系化合物 1.チオファネート メチル[“トップジン M(To
psin M)”、第1201〜1203頁] 2.ベノミル[“ベンレート(Benlate)”、第
100〜102頁] 3.カルベンダジム[“バビスチン(Bavisti
n)”、第182〜184頁] 4.チアベンダゾール[“メルテクト(Mertec
t)”、第1183〜1185頁]
D. Benzimidazole compounds 1. Thiophanate methyl [“Topzine M (To
1. psin M) ", pages 1201-1203] 2. Benomyl [" Benlate ", pages 100-102] 3. Carbendazim [" Babistin "
n) ", pp. 182-184] 4. Thiabendazole [" Mertec. "
t) ", pp. 1183-1185]

【0009】E.アニリノピリミジン系化合物 1.ピリメタニル[“スカーラ(Scala)”、第1
068〜1069頁] 2.メパニピリム[“フルピカ(Frupica)”、
第784〜785頁] 3.シプロジニル[“ユニックス”(Unix)、第3
19〜321頁]
E. Anilinopyrimidine compounds 1. Pyrimethanil [“Scala”, 1st
068-1069] 2. Mepanipyrim [“Frupica”,
784-785] 3. Cyprodinil ["Unix", 3rd
19-321]

【0010】F.アクリレート系化合物 1.クレソキシム・メチル[“ストロビー”、第743
〜744頁] 2.アゾキシストロビルリン[“ヘリテージ(Heri
tage)”、第70〜72頁] 3.特開昭63−23852号公報に記載の化合物 4.SSF−126(コード番号)[第1114〜11
15頁]
F. Acrylate-based compounds Klesoxim Methyl ["Strobe", 743
-744 pages] 2. Azoxystrovirulin [Heritage (Heri
stage) ", pp. 70-72] 3. Compounds described in JP-A-63-23852 4. SSF-126 (code number) [1114-11
15 pages]

【0011】G.その他 1.ポリオキシン[“ポリオキシン AL(Polyo
xin AL)”、第991〜994頁] 2.ノニルフェノールスルホン酸銅[“ヨネポン(Yo
nepon)”] 3.DBEDC[“サンヨール(Sanyol)”] 4.イミノクタジン・アルベシル酸塩[“ベルクート
(Bellkute)”、第709〜712頁] 5.トリフォリン[“サプロール(Saprol)”、
第1252〜1254頁] 6.フェナリモル[“ルビゲン(Rubigan)”、
第505〜506頁] 7.ヌアリモル[“トリミダール(Trimida
l)”、第889〜890頁] 8.ピリフェノックス[“ドラド(Dorado)”、
第1066〜1068頁] 9.フェンプロピジン[“ターン(Tern)”、第5
26〜527頁] 10.キノメチオネート[“モレスタン(Morest
an)”、第198〜200頁] 11.イオウ[“コサン(Cosan)”、第1133
〜1134頁] 12.フェノキシフェン[“(Quinoxyfe
n)”、第1083〜1084頁]
G. Others 1. Polyoxin ["Polyoxin AL (Polyo
xin AL) ", pp. 991-994] 2. Copper nonylphenol sulfonate [" Yonepon (Yo)
nepon) "] 3. DBEDC [" Sanyl "] 4. Iminoctadine albesylate [" Bellkute ", pages 709-712] 5. Trifolin [" Saprol ",
1252-1254] 6. Fenarimol [“Rubigan”,
Pp. 505-506] 7. Nuarimol ["Trimida
l) ", 889-890] 8. Pyrifenox [" Dorado ",
Pages 1066 to 1068] 9. Fenpropidin [“Tern”, 5th
26-527] 10. Quinomethionate [Morest
an) ", pp. 198-200] 11. Sulfur [" Cosan ", 1133
11134] 12. Phenoxyphene [“(Quinoxyfe
n) ", pp. 1083-1084]

【0012】[0012]

【発明が解決しようとする課題】本発明は、成分Iの置
換チオフェン誘導体の一つと成分IIのトリアゾール系
化合物、イミダゾール系化合物、モルフォリン系化合
物、ベンズイミダゾール系化合物、アニリノピリミジン
系化合物、アクリレート系化合物、イミノクタジン・ア
ルベシル酸塩、ポリオキシンのうちの一つとの少なくと
も二種の有効成分を含有し、うどんこ病に対して相乗的
に増強された作用を有する植物病害防除剤組成物を提供
することを目的とする。
DISCLOSURE OF THE INVENTION The present invention relates to a substituted thiophene derivative of component I and a triazole compound, imidazole compound, morpholine compound, benzimidazole compound, anilinopyrimidine compound, acrylate of component II. The present invention provides a plant disease controlling composition comprising at least two active ingredients, one of a compound, iminoctadine albesylate, and polyoxin, and having a synergistically enhanced action on powdery mildew. The purpose is to.

【0013】[0013]

【課題を解決するための手段】本発明者等は上記課題を
解決するため種々検討した結果、驚くべきことに、成分
IIのトリアゾール系化合物、イミダゾール系化合物、
モルフォリン系化合物、ベンズイミダゾール系化合物、
アニリノピリミジン系化合物、アクリレート系化合物、
イミノクタジン・アルベシル酸塩、ポリオキシンのうち
のすくなくとも一つの成分と成分Iの置換チオフェン誘
導体の一つとを混合した組成物が、広範囲の植物病害、
特にうどんこ病の病害の感染に対して増強された相乗効
果を示し、従って前記課題の解決にかなうものであるこ
とを見出し、本発明を完成した。
The present inventors have conducted various studies to solve the above-mentioned problems, and as a result, surprisingly, the triazole compound, the imidazole compound,
Morpholine compounds, benzimidazole compounds,
Anilinopyrimidine compounds, acrylate compounds,
Iminoctadine albesylate, a composition of at least one component of polyoxins and one of the substituted thiophene derivatives of component I, a wide range of plant diseases,
In particular, they have found that they show an enhanced synergistic effect on the infection of powdery mildew diseases, and therefore can solve the above problems, and thus completed the present invention.

【0014】即ち、本発明は、少なくとも2種の有効成
分を含有し、うどんこ病の感染に対して相乗効果を有す
る植物保護組成物であり、成分Iは一般式(1)(化
3)
That is, the present invention is a plant protection composition containing at least two kinds of active ingredients and having a synergistic effect against powdery mildew infection, wherein the component I has the general formula (1)

【0015】[0015]

【化3】 [式中、Qは水素原子、メチル基、トリフルオロメチル
基、フッ素原子、塩素原子、臭素原子、ヨウ素原子、メ
トキシ基、メチルスルホキシ基、メチルスルホニル基、
シアノ基、アセチル基、ニトロ基、アルコキシカルボニ
ル基またはアミノ基を示し、Rは炭素数3〜12の直鎖
または分岐のアルキル基、炭素数3〜12の直鎖または
分岐のハロゲノアルキル基、炭素数3〜10の直鎖また
は分岐のアルケニル基、炭素数3〜10の直鎖または分
岐のハロゲノアルケニル基、炭素数1〜4のアルキル基
で置換していてもよい炭素数3〜10のシクロアルキル
基、炭素数1〜4のアルキル基で置換していてもよい炭
素数3〜10のハロゲノ置換シクロアルキル基、または
1〜3個の置換基により置換されていてもよいフェニル
基であり、該フェニル基の置換基は水素原子、炭素数1
〜4のアルキル基、炭素数2〜4のアルケニル基、炭素
数2〜4のアルキニル基、炭素数3〜6のシクロアルキ
ル基、炭素数1〜4のアルコキシ基、炭素数1〜4のハ
ロゲノアルコキシ基、炭素数1〜4のアルキルチオ基、
炭素数1〜4のアルキルスルホキシ基、炭素数1〜4の
アルキルスルホニル基、ハロゲン原子、シアノ基、炭素
数2〜4のアシル基、炭素数2〜4のアルコキシカルボ
ニル基、アミノ基、または炭素数1〜3のアルキル基で
置換されたアミノ基であり、Rと−NHCOArは互い
に隣り合っており、Arは以下の(A1)から(A8)
(化3)
Embedded image [Wherein Q is a hydrogen atom, a methyl group, a trifluoromethyl group, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a methoxy group, a methylsulfoxy group, a methylsulfonyl group,
A cyano group, an acetyl group, a nitro group, an alkoxycarbonyl group or an amino group, wherein R is a straight-chain or branched alkyl group having 3 to 12 carbon atoms, a straight-chain or branched halogenoalkyl group having 3 to 12 carbon atoms, A linear or branched alkenyl group having 3 to 10 carbon atoms, a linear or branched halogenoalkenyl group having 3 to 10 carbon atoms, or a cycloalkyl having 3 to 10 carbon atoms which may be substituted with an alkyl group having 1 to 4 carbon atoms. An alkyl group, a halogeno-substituted cycloalkyl group having 3 to 10 carbon atoms which may be substituted by an alkyl group having 1 to 4 carbon atoms, or a phenyl group optionally substituted by 1 to 3 substituents; The substituent of the phenyl group is a hydrogen atom and has 1 carbon atom.
Alkyl group of 4 to 4, alkenyl group of 2 to 4 carbon atoms, alkynyl group of 2 to 4 carbon atoms, cycloalkyl group of 3 to 6 carbon atoms, alkoxy group of 1 to 4 carbon atoms, halogeno of 1 to 4 carbon atoms An alkoxy group, an alkylthio group having 1 to 4 carbon atoms,
An alkylsulfoxy group having 1 to 4 carbon atoms, an alkylsulfonyl group having 1 to 4 carbon atoms, a halogen atom, a cyano group, an acyl group having 2 to 4 carbon atoms, an alkoxycarbonyl group having 2 to 4 carbon atoms, an amino group, or An amino group substituted with an alkyl group having 1 to 3 carbon atoms, R and -NHCOAr are adjacent to each other, and Ar is represented by the following (A1) to (A8)
(Formula 3)

【0016】[0016]

【化4】 (式中、R1はトリフルオロメチル基、ジフルオロメチ
ル基、メチル基、エチル基、塩素原子、臭素原子または
ヨウ素原子であり、R2は水素原子、メチル基、トリフ
ルオロメチル基またはアミノ基であり、nは0〜2の整
数である)で表される基である]で表される置換チオフ
ェン誘導体であり、成分IIはトリアゾール系化合物、
イミダゾール系化合物、モルフォリン系化合物、ベンズ
イミダゾール系化合物、アニリノピリミジン系化合物、
アクリレート系化合物、イミノクタジン・アルベシル酸
塩、ポリオキシンのうちの少なくとも一つの化合物であ
る組成物に関する。
Embedded image (Wherein, R 1 is a trifluoromethyl group, a difluoromethyl group, a methyl group, an ethyl group, a chlorine atom, a bromine atom or an iodine atom, and R 2 is a hydrogen atom, a methyl group, a trifluoromethyl group or an amino group, n is an integer of from 0 to 2)], wherein the component II is a triazole-based compound,
Imidazole compounds, morpholine compounds, benzimidazole compounds, anilinopyrimidine compounds,
The present invention relates to a composition which is at least one compound of an acrylate compound, iminoctadine albesylate, and polyoxin.

【0017】[0017]

【発明の実施の形態】本発明の成分Iで表される化合物
のうち、好ましいものは、Arが(A1)で、R1がC
3またはMe基でありR2がMe基;Arが(A2)
で、R1がCF3またはCHF2;Arが(A3)で、R1
がMe基でありR2が水素原子またはMe基;Arが
(A4)で、R1がMe基でありnが0〜1;Arが
(A5)で、R1が塩素原子;Arが(A6)または
(A7);Arが(A8)で、R1がMe基である化合
物、Rが炭素数4〜8の直鎖または分岐のアルキル基、
または炭素数1〜4のアルキル基で置換していてもよい
炭素数4〜8のシクロアルキル基である化合物、Qが水
素原子である化合物である。
BEST MODE FOR CARRYING OUT THE INVENTION Among the compounds represented by Component I of the present invention, preferred are those wherein Ar is (A1) and R1 is C
R 3 is a Me group and R 2 is a Me group; Ar is (A2)
In, R1 is CF 3 or CHF 2; in the Ar (A3), R1
Is a Me group and R2 is a hydrogen atom or a Me group; Ar is (A4), R1 is a Me group and n is 0 to 1; Ar is (A5), R1 is a chlorine atom; Ar is (A6) or (A7): a compound wherein Ar is (A8) and R 1 is a Me group, R is a linear or branched alkyl group having 4 to 8 carbon atoms,
Or a compound having a cycloalkyl group having 4 to 8 carbon atoms which may be substituted with an alkyl group having 1 to 4 carbon atoms, or a compound wherein Q is a hydrogen atom.

【0018】本発明の成分Iとして特に好ましい化合物
は、Arが(A1)で、R1がCF3またはMe基であ
り、R2がMe基;Arが(A2)であり、R1がCF3
またはCHF2であり、Qが水素原子であり、Rが炭素
数4〜8の直鎖または分岐のアルキル基、または炭素数
1〜4のアルキル基で置換してもよい炭素数4〜8のシ
クロアルキル基である化合物である。
[0018] Particularly preferred compounds as component I of the present invention, Ar in the (A1), R1 is CF 3 or Me group, R2 is Me group; a is Ar (A2), R1 is CF 3
Or CHF 2 , Q is a hydrogen atom, and R is a linear or branched alkyl group having 4 to 8 carbon atoms, or a C 4 to C 8 alkyl group which may be substituted with an alkyl group having 1 to 4 carbon atoms. A compound that is a cycloalkyl group.

【0019】以下に、成分Iで表される化合物の具体例
の幾つかを示す。 化合物番号1:N−{2−(1,3−ジメチルブチル)
−3−チエニル}−2,4−ジメチルチアゾール−5−
カルボン酸アミド[Qが水素原子であり、Rが1,3−
ジメチルブチル基であり、ArがA1(R1=Me,R2
=Me)の場合] 化合物番号2:N−{2−(1,3−ジメチルブチル)
−3−チエニル}−3−トリフルオロメチル−1−メチ
ルピラゾール−4−カルボン酸アミド[Qが水素原子で
あり、Rが1,3−ジメチルブチル基であり、ArがA
2(R1=CF3)の場合] 化合物番号3:N−{2−(1,3−ジメチルブチル)
−3−チエニル}−2−メチルフラン−3−カルボン酸
アミド[Qが水素原子であり、Rが1,3−ジメチルブ
チル基であり、ArがA3(R1=Me,R2=H)の場
合] 化合物番号4:N−{2−(1,3−ジメチルブチル)
−3−チエニル}−3−メチルチオフェン−2−カルボ
ン酸アミド[Qが水素原子であり、Rが1,3−ジメチ
ルブチル基であり、ArがA4(R1=Me,n=0)
の場合] 化合物番号5:N−{2−(1,3−ジメチルブチル)
−3−チエニル}−2−クロロニコチン酸アミド[Qが
水素原子であり、Rが1,3−ジメチルブチル基であ
り、ArがA6の場合]
The following are some specific examples of the compound represented by Component I. Compound number 1: N- {2- (1,3-dimethylbutyl)
-3-thienyl} -2,4-dimethylthiazole-5
Carboxamide [Q is a hydrogen atom and R is 1,3-
A dimethylbutyl group, and Ar is A1 (R1 = Me, R2
= Me)] Compound number 2: N- {2- (1,3-dimethylbutyl)
-3-thienyl} -3-trifluoromethyl-1-methylpyrazole-4-carboxylic acid amide [Q is a hydrogen atom, R is a 1,3-dimethylbutyl group, and Ar is A
2 (R1 = CF 3) In the case of Compound No. 3: N- {2- (1,3- dimethylbutyl)
-3-thienyl} -2-methylfuran-3-carboxylic acid amide [when Q is a hydrogen atom, R is a 1,3-dimethylbutyl group, and Ar is A3 (R1 = Me, R2 = H) Compound number 4: N- {2- (1,3-dimethylbutyl)
-3-thienyl} -3-methylthiophene-2-carboxylic acid amide [Q is a hydrogen atom, R is a 1,3-dimethylbutyl group, and Ar is A4 (R1 = Me, n = 0)
Compound number 5: N- {2- (1,3-dimethylbutyl)
-3-thienyl} -2-chloronicotinamide [when Q is a hydrogen atom, R is a 1,3-dimethylbutyl group, and Ar is A6]

【0020】本発明の組成物は、下記の種類の植物病害
に対して有効である:イネのいもち病(Pyricularia ory
zae)、紋枯病(Rhizoctonia solani)、ごま葉枯病(Cochl
iobolus miyabeanus)、馬鹿苗病(Gibberella fujikuro
i);ムギ類のうどんこ病(Erysiphe graminis f.sp.hord
ei; f.sp.tritici)、さび病(Puccinia striiformis; P.
graminis; P.recondita; P.hordei)、斑葉病(Pyrenoph
ora graminea)、網斑病(Pyrenophora teres)、赤かび病
(Gibberella zeae)、雪腐病(Typhula sp.; Micronectri
ella nivalis)、裸黒穂病(Ustilago tritici; U.nud
a)、なまぐさ黒穂病(Tilletia caries)、眼紋病(Pseudo
cercosporella herpotrichoides)、株腐病(Rhizoctonia
cerealis)、雲形病(Rhynchosporium secalis)、葉枯病
(Septoria tritici)、ふ枯病(Leptosphaeria nodoru
m);インゲン、キュウリ、トマト、イチゴ、ブドウ、ジ
ャガイモ、ダイズ、キャベツ、ナス、レタス等の灰色か
び病(Botrytis cinerea);ブドウのべと病(Plasmopora
viticola)、さび病(Phakopsora ampelopsidis)、うどん
こ病(Uncinula necator)、黒とう病(Elsinoe ampelin
a)、晩腐病(Glomerella cingulata);リンゴのうどんこ
病(Podosphaera leucotricha)、黒星病(Venturia inaeq
ualis)、斑点落葉病(Alternaria mali)、赤星病(Gymnos
porangium yamadae)、モニリア病(Sclerotinia mali)、
腐らん病(Valsa mali);ナシの黒斑病(Alternaria kiku
chiana)、黒星病(Venturia nashicola)、赤星病(Gymnos
porangium haraeanum)、輪紋病(Physalospora piricol
a);モモの灰星病(Sclerotinia cinerea)、黒星病(Clad
osporium carpophilum)、フォモプシス腐敗病(Phomopsi
s sp.);カキの炭そ病(Gloeosporium kaki)、落葉病(Ce
rcospora kaki; Mycosphaerella nawae)、うどんこ病(P
hyllactinia kakikora);キュウリのべと病(Pseudopero
nospora cubensis)、ウリ類のうどんこ病(Sphaerotheca
fuliginea)、炭そ病(Colletotrichum lagenarium)、つ
る枯病(Mycosphaerella melonis);トマトの輪紋病(Alt
ernaria solani)、葉かび病(Cladosporium fulvam)、疫
病(Phytophthora infestans);ナスのうどんこ病(Erysi
phe cichoracorum)、すすかび病(Mycovellosiella natt
rassii); アブラナ科野菜の黒斑病(Alternaria japoni
ca)、白斑病(Cercosporella brassicae);ネギのさび病
(Puccinia allii)、黒斑病(Alternaria porri); ダイ
ズの紫斑病(Cercospora kikukuchii)、黒とう病(Elsino
e glycinnes)、黒点病(Diaporthe phaseololum);イン
ゲンの炭そ病(Colletotrichum lindemuthianum);ラッ
カセイの黒渋病(Mycosphaerellapersonatum)、褐斑病(C
ercospora arachidicola);エンドウのうどんこ病(Erys
iphe pisi)、べと病(Peronospora pisi);ジャガイモの
夏疫病(Alternaria solani)、黒あざ病(Rhizoctonia so
lani)、疫病(Phytophthora infestans);ソラマメのべ
と病(Peronospora viciae)、疫病(Phytophthora nicoti
anae);チャの網もち病(Exobasidium reticulatum)、白
星病(Elsinoe leucospila)、炭そ病(Colletotrichum t
heae-sinensis);タバコの赤星病(Alternaria longipe
s)、うどんこ病(Erysiphe cichoracearum)、 炭そ病(Co
lletotrichum tabacum)、疫病(Phytophthora parasitic
a);テンサイの褐斑病(Cercospora beticola); バラの
黒星病(Diplocarpon rosae)、うどんこ病(Sphaerotheca
pannosa)、疫病(Phytophthora megasperma); キクの
褐斑病(Septoria chrysanthemi-indici)、白さび病(Puc
cinia horiana);イチゴのうどんこ病(Sphaerotheca hu
muli)、疫病(Phytophthora nicotianae);インゲン、キ
ュウリ、トマト、イチゴ、ブドウ、ジャガイモ、ダイ
ズ、キャベツ、ナス、レタス等の菌核病(Sclerotinia s
clerotiorum);カンキツの黒点病(Diaporthe citri);
ニンジンの黒葉枯病(Alternaria dauci)等。なかでも、
うどんこ病に対して相乗的に増強された効果を有する。
このような増強作用は、個々の有効成分の作用の合計か
らは予期されることではなかった。
The compositions of the present invention are effective against the following types of plant diseases: Pyricularia ory
zae ), sheath blight ( Rhizoctonia solani ), sesame leaf blight ( Cochl
iobolus miyabeanus ), idiot disease ( Gibberella fujikuro)
i ); Powdery mildew of wheat ( Erysiphe graminis f.sp. hord)
ei; f.sp. tritici), rust (Puccinia striiformis; P.
graminis ; P. recondita ; P. hordei) , leaf spot disease ( Pyrenoph
ora graminea ), net spot disease (Pyrenophora teres ), Fusarium head blight
( Gibberella zeae ), snow rot ( Typhula sp .; Micronectri
ella nivalis ), nude smut ( Ustilago tritic i; U. nud)
a ), black smut ( Tilletia caries ), eye spot disease ( Pseudo
cercosporella herpotrichoides ), strain rot ( Rhizoctonia
cerealis), scald (Rhynchosporium secalis), leaf blight
( Septoria tritici ), blight ( Leptosphaeria nodoru)
m ); Botrytis cinerea such as bean, cucumber, tomato, strawberry, grape, potato, soybean, cabbage, eggplant, lettuce; and downy mildew of grape ( Plasmopora)
viticola), rust (Phakopsora ampelopsidis), powdery mildew (Uncinula necator), sphaceloma disease (Elsinoe ampelin
a ), late rot ( Glomerella cingulata ); powdery mildew on apples ( Podosphaera leucotricha ), scab ( Venturia inaeq)
ualis ), spot leaf rot ( Alternaria mali ), scab ( Gymnos )
porangium yamadae ), Monilia disease ( Sclerotinia mali ),
Rot rot ( Valsa mali ); Black spot of pear ( Alternaria kiku)
chiana), scab (Venturia nashicola), gymnosporangium (Gymnos
porangium haraeanum ), ring spot disease ( Physalospora piricol )
a ); Peach ash disease ( Sclerotinia cinerea ), scab ( Clad )
osporium carpophilum), Phomopsis rot (Phomopsi
s sp.); oyster anthracnose ( Gloeosporium kaki ), leaf blight ( Ce )
rcospora kaki ; Mycosphaerella nawae ), powdery mildew ( P
hyllactinia kakikora ); downy mildew of cucumber ( Pseudopero
nospora cubensis ), powdery mildew of cucumber ( Sphaerotheca
fuliginea ), Anthracnose ( Colletotrichum lagenarium ), Vine blight ( Mycosphaerella melonis ); Tomato ring spot ( Alt
ernaria solani ), leaf mold ( Cladosporium fulvam ), plague ( Phytophthora infestans ); eggplant powdery mildew ( Erysi
phe cichoracorum), Susukabi disease (Mycovellosiella natt
rassii ); Black spot of cruciferous vegetables ( Alternaria japoni
ca ), white spot disease ( Cercosporella brassicae );
(Puccinia allii), black spot disease (Alternaria porri); soybean purpura (Cercospora kikukuchii), sphaceloma disease (Elsino
e glycinnes ), black spot ( Diaporthe phaseololum ); kidney anthracnose ( Colletotrichum lindemuthianum ); peanut black spot ( Mycosphaerellapersonatum ), brown spot ( C
ercospora arachidicola ); powdery mildew of pea ( Erys
iphe pisi ), downy mildew ( Peronospora pisi ); potato summer plague ( Alternaria solani ), black bruise ( Rhizoctonia so
lani ), plague ( Phytophthora infestans ); broad bean downy mildew ( Peronospora viciae ), plague ( Phytophthora nicoti )
anae ); Tea blast ( Exobasidium reticulatum ), white scab ( Elsinoe leucospila ), anthracnose ( Colletotrichum t
heae-sinensis); Tobacco scab ( Alternaria longipe)
s ), powdery mildew ( Erysiphe cichoracearum ), anthracnose ( Co
lletotrichum tabacum ), plague ( Phytophthora parasitic )
a ); Brown spot of sugar beet ( Cercospora beticola ); Rose scab ( Diplocarpon rosae ), powdery mildew ( Sphaerotheca )
pannosa ), plague ( Phytophthora megasperma ); chrysanthemum leaf spot ( Septoria chrysanthemi - indici ), white rust ( Puc
cinia horiana ); strawberry powdery mildew ( Sphaerotheca hu)
muli ), plague ( Phytophthora nicotianae ); sclerotium disease (S clerotinia s
clerotiorum ); citrus black spot ( diaporthe citri );
Bacterial leaf blight of carrots ( Alternaria dauci ) and the like. Above all,
It has a synergistically enhanced effect on powdery mildew.
Such a potentiating effect was not to be expected from the sum of the effects of the individual active ingredients.

【0021】本発明の組成物において、成分Iの置換チ
オフェン誘導体と成分IIの混合割合は特に限定されな
いが、通常、成分Iの化合物1重量部に対して成分II
の化合物は0.01〜50重量部、好ましくは0.5〜
50重量部、より好ましくは0.5〜30重量部、より
一層好ましくは1〜20重量部の範囲内である。
In the composition of the present invention, the mixing ratio of the substituted thiophene derivative of the component I and the component II is not particularly limited.
Is from 0.01 to 50 parts by weight, preferably from 0.5 to 50 parts by weight.
It is in the range of 50 parts by weight, more preferably 0.5 to 30 parts by weight, even more preferably 1 to 20 parts by weight.

【0022】本発明の組成物は、2種の有効成分を含む
混合物を直接施用しても良いし、個々の有効成分を別々
に同時施用するか、または相前後して施用しても良い。
更に、有効成分を含む混合物は、2種の有効成分を含む
濃厚組成物を水で希釈しても良いし、また、個々の有効
成分を含む2種の濃厚液から使用時に混合物を調製し、
これを水で希釈しても良い(タンクミックス法)。本発
明組成物を植物病害防除剤として使用する場合は、処理
する植物に対して原体をそのまま使用してもよいが、一
般には不活性な液体担体、固体担体、界面活性剤と混合
し、通常用いられる製剤形態である粉剤、水和剤、フロ
アブル剤、乳剤、粒剤およびその他の一般に慣用される
形態の製剤として使用される。更に製剤上必要ならば補
助剤を添加することもできる。
The composition of the present invention may be applied directly as a mixture containing the two active ingredients, or may be applied separately or simultaneously, or may be applied one after the other.
Further, the mixture containing the active ingredients may be obtained by diluting the concentrated composition containing the two active ingredients with water, or preparing the mixture at the time of use from the two concentrated liquids containing the individual active ingredients,
This may be diluted with water (tank mix method). When the composition of the present invention is used as a plant disease controlling agent, the drug substance may be used as it is for the plant to be treated, but it is generally mixed with an inert liquid carrier, a solid carrier, a surfactant, It is used in the form of powders, wettable powders, flowables, emulsions, granules and other commonly used forms which are commonly used. If necessary for the preparation, an auxiliary agent can be added.

【0023】ここでいう担体とは、処理すべき部位への
有効成分の到達を助け、また有効成分化合物の貯蔵、輸
送、取扱いを容易にするために配合される合成または天
然の無機または有機物質を意味する。担体としては、通
常農園芸用薬剤に使用されるものであるならば固体また
は液体のいずれでも使用でき、特定のものに限定される
ものではない。
As used herein, the term "carrier" refers to a synthetic or natural inorganic or organic substance incorporated to help the active ingredient reach the site to be treated and to facilitate storage, transport, and handling of the active ingredient compound. Means As the carrier, any solid or liquid carrier can be used as long as it is generally used for agricultural and horticultural medicines, and it is not limited to a specific one.

【0024】例えば、固体担体としては、モンモリロナ
イト、カオリナイト等の粘土類;珪藻土、白土、タル
ク、バ−ミュキュライト、石膏、炭酸カルシウム、シリ
カゲル、硫安等の無機物質;大豆粉、鋸屑、小麦粉等の
植物性有機物質および尿素等が挙げられる。物性を改良
するために、高分散ケイ酸または高分散吸収性ポリマー
を添加することも可能である。液体担体としては、トル
エン、キシレン、クメン等の芳香族炭化水素類;ケロシ
ン、鉱油などのパラフィン系炭化水素類;アセトン、メ
チルエチルケトン、シクロヘキサノンなどのケトン類;
ジオキサン、ジエチレングリコールジメチルエーテルな
どのエーテル類;メタノール、エタノール、プロパノー
ル、エチレングリコールなどのアルコール類;ジメチル
ホルムアミド、ジメチルスルホキシドなどの非プロトン
性溶媒および水等が挙げられる。
For example, solid carriers include clays such as montmorillonite and kaolinite; diatomaceous earth, terra alba, talc, vermiculite, gypsum, calcium carbonate, silica gel, and ammonium sulfate; inorganic substances such as soybean powder, sawdust, flour, etc. Plant organic substances and urea. In order to improve the physical properties, it is also possible to add a highly dispersed silicic acid or a highly dispersed absorbent polymer. As the liquid carrier, aromatic hydrocarbons such as toluene, xylene and cumene; paraffinic hydrocarbons such as kerosene and mineral oil; ketones such as acetone, methyl ethyl ketone and cyclohexanone;
Ethers such as dioxane and diethylene glycol dimethyl ether; alcohols such as methanol, ethanol, propanol and ethylene glycol; aprotic solvents such as dimethylformamide and dimethyl sulfoxide; and water.

【0025】更に、製剤の剤型、適用場面等を考慮して
目的に応じてそれぞれ単独に、または組み合わせて次の
様な補助剤を添加することができる。補助剤としては、
通常使用される界面活性剤、結合剤(例えば、リグニン
スルホン酸、アルギン酸、ポリビニルアルコール、アラ
ビアゴム、CMCナトリウム等)、安定剤(例えば、酸
化防止用としてフェノール系化合物、チオール系化合物
または高級脂肪酸エステル等を用いたり、pH調整剤と
して燐酸塩を用いたり、時に光安定剤も用いる)等を必
要に応じて単独または組み合わせて使用できる。更に場
合によっては防菌防黴のために工業用殺菌剤、防菌防黴
剤などを添加することもできる。
Further, the following adjuvants can be added singly or in combination according to the purpose in consideration of the dosage form of the preparation, the application scene, and the like. As auxiliary agents,
Commonly used surfactants, binders (eg, ligninsulfonic acid, alginic acid, polyvinyl alcohol, gum arabic, sodium CMC, etc.), stabilizers (eg, phenolic compounds, thiol compounds, or higher fatty acid esters for antioxidation) Etc., a phosphate as a pH adjuster, and sometimes a light stabilizer) can be used alone or in combination as necessary. Further, depending on the case, an industrial bactericide, a bactericidal / antifungal agent or the like may be added for bactericidal / fungicidal purposes.

【0026】補助剤について更に詳しく述べる。補助剤
としては乳化、分散、拡展、湿潤、結合、安定化等の目
的ではリグニンスルホン酸塩、アルキルベンゼンスルホ
ン酸塩、アルキル硫酸エステル塩、ポリオキシアルキレ
ンアルキル硫酸塩、ポリオキシアルキレンアルキルリン
酸エステル塩等のアニオン性界面活性剤;ポリオキシア
ルキレンアルキルエーテル、ポリオキシアルキレンアル
キルアリールエーテル、ポリオキシアルキレンアルキル
アミン、ポリオキシアルキレンアルキルアミド、ポリオ
キシアルキレンアルキルアミド、ポリオキシアルキレン
アルキルチオエーテル、ポリオキシアルキレン脂肪酸エ
ステル、グリセリン脂肪酸エステル、ソルビタン脂肪酸
エステル、ポリオキシアルキレンソルビタン脂肪酸エス
テル、ポリオキシプロピレンポリオキシエチレンブロッ
クポリマー等の非イオン性界面活性剤;ステアリン酸カ
ルシウム、ワックス等の滑剤;イソプロピルヒドロジエ
ンホスフェート等の安定剤;ホスファチジルエタノール
アミン、ホスファチジルセリン、ホスファチジルグリセ
ロール、リゾレシチン等のセファリンまたはレシチン系
の天然または合成リン脂質;その他メチルセルロース、
カルボキシメチルセルロース、カゼイン、アラビアゴム
等が挙げられる。しかし、これらの成分は以上のものに
限定されるものではない。
The adjuvant will be described in more detail. Auxiliaries include lignin sulfonate, alkylbenzene sulfonate, alkyl sulfate, polyoxyalkylene alkyl sulfate, polyoxyalkylene alkyl phosphate for the purpose of emulsification, dispersion, spreading, wetting, bonding, stabilization, etc. Anionic surfactants such as salts; polyoxyalkylene alkyl ethers, polyoxyalkylene alkylaryl ethers, polyoxyalkylene alkylamines, polyoxyalkylene alkylamides, polyoxyalkylene alkylamides, polyoxyalkylene alkylthioethers, polyoxyalkylene fatty acids Ester, glycerin fatty acid ester, sorbitan fatty acid ester, polyoxyalkylene sorbitan fatty acid ester, polyoxypropylene polyoxyethylene block polymer Nonionic surfactants; lubricants such as calcium stearate and wax; stabilizers such as isopropylhydrodiene phosphate; cephalin or lecithin-based natural or synthetic phospholipids such as phosphatidylethanolamine, phosphatidylserine, phosphatidylglycerol, and lysolecithin; Methyl cellulose,
Carboxymethyl cellulose, casein, gum arabic and the like can be mentioned. However, these components are not limited to those described above.

【0027】本発明組成物における有効成分組成物の含
有量は、製剤形態によっても異なるが、通常粉剤では
0.1〜30重量%、水和剤では0.1〜80重量%、
粒剤では0.5〜20重量%、乳剤では2〜50重量
%、フロアブル製剤では1〜50重量%、ドライフロア
ブル製剤では1〜80重量%であり、好ましくは、粉剤
では0.5〜10重量%、水和剤では5〜60重量%、
乳剤では5〜20重量%、フロアブル製剤では5〜50
重量%およびドライフロアブル製剤では5〜50重量%
である。補助剤の含有量は0〜80重量%であり、担体
の含有量は100重量%から有効成分化合物のおよび補
助剤の含有量を差し引いた量である。
The content of the active ingredient composition in the composition of the present invention varies depending on the form of preparation, but is usually 0.1 to 30% by weight for powders and 0.1 to 80% by weight for wettable powders.
It is 0.5 to 20% by weight for granules, 2 to 50% by weight for emulsions, 1 to 50% by weight for flowable preparations, 1 to 80% by weight for dry flowable preparations, and preferably 0.5 to 10% for powders. % By weight, 5-60% by weight for wettable powder,
5-20% by weight for emulsions, 5-50% for flowable formulations
Wt% and 5-50 wt% for dry flowable formulations
It is. The content of the adjuvant is 0 to 80% by weight, and the content of the carrier is 100% by weight minus the content of the active ingredient compound and the content of the adjuvant.

【0028】本発明組成物の施用方法としては種子処
理、茎葉散布、土壌潅注等が挙げられるが、通常当業者
が利用するどの様な施用方法にても十分な効力を発揮す
る。施用量および施用濃度は対象作物、対象病害、病害
の発生程度、化合物の剤型、施用方法および各種環境条
件等によって変動するが、散布する場合には有効成分量
としてヘクタール当たり50〜1,000gが適当であ
り、望ましくはヘクタール当り100〜500gであ
る。また水和剤、フロアブル剤または乳剤を水で希釈し
て散布する場合、その希釈倍率は200〜20,000
倍が適当であり、望ましくは500〜5,000倍であ
る。また、種子消毒の場合、殺菌剤混合物の使用量は、
種子1kg当たり0.001から50g、好ましくは
0.01から10gである。本発明の組成物は他の殺菌
剤、殺虫剤、殺ダニ剤、殺線虫剤、除草剤および植物成
長調節剤等の農薬、土壌改良剤または肥効物質との混合
使用は勿論のこと、これらとの混合製剤も可能である。
Examples of the method of applying the composition of the present invention include seed treatment, foliage application, soil irrigation, etc., and any application method usually used by those skilled in the art exerts sufficient effects. The application rate and application concentration vary depending on the target crop, the target disease, the degree of occurrence of the disease, the dosage form of the compound, the application method and various environmental conditions, etc., but when sprayed, the active ingredient amount is 50 to 1,000 g per hectare. Is suitable, desirably from 100 to 500 g per hectare. When a wettable powder, a flowable or an emulsion is diluted with water and sprayed, the dilution ratio is 200 to 20,000.
A factor of 2 is appropriate, preferably a factor of 500 to 5,000. In the case of seed disinfection, the amount of fungicide mixture used is
It is 0.001 to 50 g, preferably 0.01 to 10 g per kg of seed. The composition of the present invention may be used in combination with other fungicides, pesticides, acaricides, nematicides, herbicides, pesticides such as plant growth regulators, soil improvers or fertilizers, Mixed preparations with these are also possible.

【0029】次に、製剤例および試験例にて本発明を更
に詳しく説明する。尚、製剤例中の部は重量部を表す。
Next, the present invention will be described in more detail with reference to formulation examples and test examples. The parts in the preparation examples represent parts by weight.

【0030】[0030]

【実施例】製剤例 1(水和剤) 化合物番号2:10部、チオファネートメチル:20
部、リグニンスルホン酸ナトリウム:10部、アルキル
ベンゼンスルホン酸ナトリウム:20部および珪藻土:
40部を粉砕混合して、水和剤を得た。
EXAMPLES Formulation Example 1 (Wettable powder) Compound No. 2: 10 parts, thiophanate methyl: 20
Parts, sodium ligninsulfonate: 10 parts, sodium alkylbenzenesulfonate: 20 parts and diatomaceous earth:
40 parts were pulverized and mixed to obtain a wettable powder.

【0031】製剤例 2(フロアブル剤) 化合物番号2:10部、メパニピリム:10部、プロピ
レングリコール:3部、リグニンスルホン酸ナトリウ
ム:2部、ジオクチルスルホサクシネートナトリウム
塩:1部、および水:74部をサンドグラインダーで湿
式粉砕しフロアブル剤を得た。
Formulation Example 2 (Floable Agent) Compound No. 2: 10 parts, mepanipyrim: 10 parts, propylene glycol: 3 parts, sodium ligninsulfonate: 2 parts, dioctyl sulfosuccinate sodium salt: 1 part, and water: 74 The part was wet-pulverized with a sand grinder to obtain a flowable agent.

【0032】製剤例 3(フロアブル剤) 化合物番号2:10部、イミノクタジン・アルベシル酸
塩:20部、ポリオキシエチレンソルビタンモノオレエ
ート:3部、カルボキシメチルセルロ−ス:3部および
水:64部をサンドグラインダーで湿式粉砕しフロアブ
ル剤を得た。
Formulation Example 3 (Floable agent) Compound No. 2: 10 parts, iminoctadine albesylate: 20 parts, polyoxyethylene sorbitan monooleate: 3 parts, carboxymethyl cellulose: 3 parts, and water: 64 parts Was wet-pulverized with a sand grinder to obtain a flowable agent.

【0033】試験例1 キュウリうどんこ病防除試験 温室内で直径7.5cmのプラスチックポットに1.5
葉期まで2本ずつ生育させたキュウリ(品種:相模半
白)に、製剤例3に準じて調製した水和剤を所定濃度
(有効成分濃度200ppm)に希釈して、3ポット当
たり50mlずつ散布した。薬液が乾いた後、少量の展
着剤を加えた水にキュウリうどんこ病分生胞子を懸濁し
て調製した分生胞子懸濁液(1×106個/ml)を噴
霧接種し温室内に7日間保った。接種7日後、キュウリ
1葉当たりにうどんこ病の病斑が占める面積を次の指標
に従って調査して発病度を求め、下記の式に従って防除
価を算出した。結果を第1表(表1)に示す。
Test Example 1 Cucumber Powdery Mildew Control Test In a greenhouse, a 1.5 cm plastic pot was placed in a 7.5 cm diameter plastic pot.
A wettable powder prepared according to Formulation Example 3 was diluted to a predetermined concentration (active ingredient concentration: 200 ppm) in cucumber (cultivar: Sagamihanjiro) grown two by two until the leaf stage, and sprayed at 50 ml per three pots. did. After the drug solution dries, a conidia spore suspension (1 × 10 6 cells / ml) prepared by suspending cucumber powdery mildew conidia in water containing a small amount of a spreading agent is sprayed and inoculated in a greenhouse. For 7 days. Seven days after inoculation, the area occupied by the powdery mildew spot per cucumber leaf was investigated according to the following index to determine the degree of disease, and the control value was calculated according to the following formula. The results are shown in Table 1 (Table 1).

【0034】 各処理区および無処理区の平均値を発病度とした。 防除価(%)=(1−処理区の発病度/無処理区の発病
度)×100
[0034] The average value of each treated section and the untreated section was defined as the disease severity. Control value (%) = (1−Severity of treated group / Severity of untreated group) × 100

【0035】[0035]

【表1】 [Table 1]

【0036】[0036]

【発明の効果】本発明は、少なくとも2種の有効成分を
含む植物病害防除剤組成物であり、広範囲の植物病害、
特にうどんこ病に対して相乗的に増強された効果を示す
ことから、植物病害防除剤組成物として有用である。本
発明の組成物を使用することにより、慣用の方法に比べ
て予期しない少量の有効成分量で、効果的に病害の防除
ができる。うどんこ病に対する相乗効果のほか、本発明
の組成物は灰色かび病、赤さび病等に対する効果を示
す。
Industrial Applicability The present invention is a plant disease controlling composition containing at least two kinds of active ingredients, and has a wide range of plant diseases,
In particular, it shows a synergistically enhanced effect on powdery mildew and is therefore useful as a plant disease controlling agent composition. By using the composition of the present invention, it is possible to effectively control a disease with an unexpectedly small amount of an active ingredient as compared with a conventional method. In addition to the synergistic effect on powdery mildew, the composition of the present invention shows an effect on gray mold, red rust and the like.

───────────────────────────────────────────────────── フロントページの続き (51)Int.Cl.7 識別記号 FI テーマコート゛(参考) A01N 47/34 A01N 47/34 D 47/44 47/44 Fターム(参考) 4H011 AA01 AA03 BA06 BB06 BB08 BB09 BB10 BB11 DA15 DD03 DF04 ──────────────────────────────────────────────────の Continued on the front page (51) Int.Cl. 7 Identification symbol FI theme coat ゛ (reference) A01N 47/34 A01N 47/34 D 47/44 47/44 F term (reference) 4H011 AA01 AA03 BA06 BB06 BB08 BB09 BB10 BB11 DA15 DD03 DF04

Claims (7)

【特許請求の範囲】[Claims] 【請求項1】 少なくとも2種の有効成分を含有し、う
どんこ病の感染に対して相乗効果を有する植物病害防除
剤組成物であり、成分Iは一般式(1)(化1) 【化1】 [式中、Qは水素原子、メチル基、トリフルオロメチル
基、フッ素原子、塩素原子、臭素原子、ヨウ素原子、メ
トキシ基、メチルスルホキシ基、メチルスルホニル基、
シアノ基、アセチル基、ニトロ基、アルコキシカルボニ
ル基またはアミノ基を示し、Rは炭素数3〜12の直鎖
または分岐のアルキル基、炭素数3〜12の直鎖または
分岐のハロゲノアルキル基、炭素数3〜10の直鎖また
は分岐のアルケニル基、炭素数3〜10の直鎖または分
岐のハロゲノアルケニル基、炭素数1〜4のアルキル基
で置換していてもよい炭素数3〜10のシクロアルキル
基、炭素数1〜4のアルキル基で置換していてもよい炭
素数3〜10のハロゲノ置換シクロアルキル基、または
1〜3個の置換基により置換されていてもよいフェニル
基であり、該フェニル基の置換基は水素原子、炭素数1
〜4のアルキル基、炭素数2〜4のアルケニル基、炭素
数2〜4のアルキニル基、炭素数3〜6のシクロアルキ
ル基、炭素数1〜4のアルコキシ基、炭素数1〜4のハ
ロゲノアルコキシ基、炭素数1〜4のアルキルチオ基、
炭素数1〜4のアルキルスルホキシ基、炭素数1〜4の
アルキルスルホニル基、ハロゲン原子、シアノ基、炭素
数2〜4のアシル基、炭素数2〜4のアルコキシカルボ
ニル基、アミノ基、または炭素数1〜3のアルキル基で
置換されたアミノ基であり、Rと−NHCOArは互い
に隣り合っており、Arは以下の(A1)から(A8)
(化2) 【化2】 (式中、R1はトリフルオロメチル基、ジフルオロメチ
ル基、メチル基、エチル基、塩素原子、臭素原子または
ヨウ素原子であり、R2は水素原子、メチル基、トリフ
ルオロメチル基またはアミノ基であり、nは0〜2の整
数である)で表される基である]で表される置換チオフ
ェン誘導体であり、成分IIはトリアゾール系化合物、
イミダゾール系化合物、モルフォリン系化合物、ベンズ
イミダゾール系化合物、アニリノピリミジン系化合物、
アクリレート系化合物、イミノクタジン・アルベシル酸
塩、ポリオキシンのうちの少なくとも一つの化合物であ
る組成物。
1. A plant disease controlling composition comprising at least two active ingredients and having a synergistic effect on powdery mildew infection, wherein component I is represented by the general formula (1): 1) [Wherein Q is a hydrogen atom, a methyl group, a trifluoromethyl group, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a methoxy group, a methylsulfoxy group, a methylsulfonyl group,
A cyano group, an acetyl group, a nitro group, an alkoxycarbonyl group or an amino group, wherein R is a straight-chain or branched alkyl group having 3 to 12 carbon atoms, a straight-chain or branched halogenoalkyl group having 3 to 12 carbon atoms, A linear or branched alkenyl group having 3 to 10 carbon atoms, a linear or branched halogenoalkenyl group having 3 to 10 carbon atoms, or a cycloalkyl having 3 to 10 carbon atoms which may be substituted with an alkyl group having 1 to 4 carbon atoms. An alkyl group, a halogeno-substituted cycloalkyl group having 3 to 10 carbon atoms which may be substituted by an alkyl group having 1 to 4 carbon atoms, or a phenyl group optionally substituted by 1 to 3 substituents; The substituent of the phenyl group is a hydrogen atom and has 1 carbon atom.
Alkyl group of 4 to 4, alkenyl group of 2 to 4 carbon atoms, alkynyl group of 2 to 4 carbon atoms, cycloalkyl group of 3 to 6 carbon atoms, alkoxy group of 1 to 4 carbon atoms, halogeno of 1 to 4 carbon atoms An alkoxy group, an alkylthio group having 1 to 4 carbon atoms,
An alkylsulfoxy group having 1 to 4 carbon atoms, an alkylsulfonyl group having 1 to 4 carbon atoms, a halogen atom, a cyano group, an acyl group having 2 to 4 carbon atoms, an alkoxycarbonyl group having 2 to 4 carbon atoms, an amino group, or An amino group substituted with an alkyl group having 1 to 3 carbon atoms, R and -NHCOAr are adjacent to each other, and Ar is represented by the following (A1) to (A8)
(Chemical formula 2) (Wherein, R 1 is a trifluoromethyl group, a difluoromethyl group, a methyl group, an ethyl group, a chlorine atom, a bromine atom or an iodine atom, and R 2 is a hydrogen atom, a methyl group, a trifluoromethyl group or an amino group, n is an integer of from 0 to 2)], wherein the component II is a triazole-based compound,
Imidazole compounds, morpholine compounds, benzimidazole compounds, anilinopyrimidine compounds,
A composition which is at least one compound of an acrylate compound, iminoctadine albesylate, and polyoxin.
【請求項2】 成分Iにおいて、Qは水素原子であり、
Rは炭素数5〜8の直鎖または分岐のアルキル基、また
は炭素数1〜4のアルキル基で置換していてもよい炭素
数5〜8のシクロアルキル基である請求項1記載の組成
物。
2. In the component I, Q is a hydrogen atom,
The composition according to claim 1, wherein R is a linear or branched alkyl group having 5 to 8 carbon atoms, or a cycloalkyl group having 5 to 8 carbon atoms which may be substituted with an alkyl group having 1 to 4 carbon atoms. .
【請求項3】 成分IIがベンズイミダゾール系化合物
である請求項1又は2記載の組成物。
3. The composition according to claim 1, wherein the component II is a benzimidazole compound.
【請求項4】 ベンズイミダゾール系化合物がチオファ
ネートメチルである請求項3記載の組成物。
4. The composition according to claim 3, wherein the benzimidazole compound is thiophanate methyl.
【請求項5】 成分IIがアニリノピリミジン系化合物
である請求項1又は2記載の組成物。
5. The composition according to claim 1, wherein the component II is an anilinopyrimidine compound.
【請求項6】 アニリノピリミジン系化合物がメパニピ
リムである請求項5記載の組成物。
6. The composition according to claim 5, wherein the anilinopyrimidine compound is mepanipyrim.
【請求項7】 成分IIがイミノクタジン・アルベシル
酸塩である請求項1又は2記載の組成物。
7. The composition according to claim 1, wherein component II is iminoctadine albesylate.
JP24940099A 1999-09-03 1999-09-03 Plant disease control composition Expired - Lifetime JP4090639B2 (en)

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