JPH11302111A - Composition of plant disease injury controlling agent - Google Patents
Composition of plant disease injury controlling agentInfo
- Publication number
- JPH11302111A JPH11302111A JP11558498A JP11558498A JPH11302111A JP H11302111 A JPH11302111 A JP H11302111A JP 11558498 A JP11558498 A JP 11558498A JP 11558498 A JP11558498 A JP 11558498A JP H11302111 A JPH11302111 A JP H11302111A
- Authority
- JP
- Japan
- Prior art keywords
- group
- carbon atoms
- component
- compound
- substituted
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 52
- 201000010099 disease Diseases 0.000 title claims abstract description 29
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 title claims abstract description 29
- 230000006378 damage Effects 0.000 title abstract 2
- 208000027418 Wounds and injury Diseases 0.000 title 1
- 208000014674 injury Diseases 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 38
- -1 (substituted)phenyl Chemical group 0.000 claims abstract description 33
- 239000004480 active ingredient Substances 0.000 claims abstract description 20
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 17
- 101000623895 Bos taurus Mucin-15 Proteins 0.000 claims abstract description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 9
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 8
- WLLGXSLBOPFWQV-UHFFFAOYSA-N MGK 264 Chemical compound C1=CC2CC1C1C2C(=O)N(CC(CC)CCCC)C1=O WLLGXSLBOPFWQV-UHFFFAOYSA-N 0.000 claims abstract description 6
- 208000015181 infectious disease Diseases 0.000 claims abstract description 6
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 claims abstract description 5
- 239000005842 Thiophanate-methyl Substances 0.000 claims abstract description 5
- QXJKBPAVAHBARF-BETUJISGSA-N procymidone Chemical compound O=C([C@]1(C)C[C@@]1(C1=O)C)N1C1=CC(Cl)=CC(Cl)=C1 QXJKBPAVAHBARF-BETUJISGSA-N 0.000 claims abstract description 5
- 239000000126 substance Substances 0.000 claims abstract description 5
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- QGHREAKMXXNCOA-UHFFFAOYSA-N thiophanate-methyl Chemical group COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC QGHREAKMXXNCOA-UHFFFAOYSA-N 0.000 claims abstract description 4
- 125000005843 halogen group Chemical group 0.000 claims abstract description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 56
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
- 125000003277 amino group Chemical group 0.000 claims description 8
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 7
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- 229910052740 iodine Inorganic materials 0.000 claims description 6
- 125000003342 alkenyl group Chemical group 0.000 claims description 5
- TWFZGCMQGLPBSX-UHFFFAOYSA-N carbendazim Chemical compound C1=CC=C2NC(NC(=O)OC)=NC2=C1 TWFZGCMQGLPBSX-UHFFFAOYSA-N 0.000 claims description 5
- 229910052801 chlorine Inorganic materials 0.000 claims description 5
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 5
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 4
- RIOXQFHNBCKOKP-UHFFFAOYSA-N benomyl Chemical compound C1=CC=C2N(C(=O)NCCCC)C(NC(=O)OC)=NC2=C1 RIOXQFHNBCKOKP-UHFFFAOYSA-N 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- ONUFESLQCSAYKA-UHFFFAOYSA-N iprodione Chemical compound O=C1N(C(=O)NC(C)C)CC(=O)N1C1=CC(Cl)=CC(Cl)=C1 ONUFESLQCSAYKA-UHFFFAOYSA-N 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- FSCWZHGZWWDELK-UHFFFAOYSA-N 3-(3,5-dichlorophenyl)-5-ethenyl-5-methyl-2,4-oxazolidinedione Chemical compound O=C1C(C)(C=C)OC(=O)N1C1=CC(Cl)=CC(Cl)=C1 FSCWZHGZWWDELK-UHFFFAOYSA-N 0.000 claims description 3
- 239000005867 Iprodione Substances 0.000 claims description 3
- MITFXPHMIHQXPI-UHFFFAOYSA-N benzoxaprofen Natural products N=1C2=CC(C(C(O)=O)C)=CC=C2OC=1C1=CC=C(Cl)C=C1 MITFXPHMIHQXPI-UHFFFAOYSA-N 0.000 claims description 3
- 125000001188 haloalkyl group Chemical group 0.000 claims description 3
- WJCNZQLZVWNLKY-UHFFFAOYSA-N thiabendazole Chemical compound S1C=NC(C=2NC3=CC=CC=C3N=2)=C1 WJCNZQLZVWNLKY-UHFFFAOYSA-N 0.000 claims description 3
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 2
- 125000002252 acyl group Chemical group 0.000 claims description 2
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- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 2
- 125000005332 alkyl sulfoxy group Chemical group 0.000 claims description 2
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- 239000006013 carbendazim Substances 0.000 claims description 2
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 125000001153 fluoro group Chemical group F* 0.000 claims description 2
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 2
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
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- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
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- 235000014113 dietary fatty acids Nutrition 0.000 description 5
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- 238000000034 method Methods 0.000 description 4
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Landscapes
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
Description
【0001】[0001]
【発明の属する技術分野】本発明は、少なくとも2種の
有効成分を有し、病害の感染に対して相乗的に増強され
た効果を有する植物保護組成物である。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、他方がジカルボキシイミド系化合物、
ベンズイミダゾール系化合物、カーバメート系化合物か
ら選ばれる化合物のうちの少なくとも一つを含有するで
ある殺菌剤組成物に関する。FIELD OF THE INVENTION The present invention relates to a plant protection composition having at least two active ingredients and having a synergistically enhanced effect on disease infection. More specifically,
One of the active ingredients is a substituted thiophene derivative showing a plant disease controlling action, and the other is a dicarboximide compound,
The present invention relates to a fungicidal composition containing at least one compound selected from a benzimidazole compound and a carbamate compound.
【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はジカルボキシイミド系化
合物、ベンズイミダゾール系化合物、カーバメート系化
合物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 Pesticide
Manual)、第11版、The BritishC
rop Protection Council、19
97年]の記載頁を示す。 A.ジカルボキシイミド系化合物 1.プロシミドン[“スミレックス(Sumile
x)”、第1003〜1004頁] 2.ビンクロゾリン[“ロニラン(Ronila
n)”、第1267〜1269頁] 3.イプロジオン[“ロブラール”(Rovral)、
第724〜726頁]B.ベンズイミダゾール系化合物 4.チオファネート メチル[“トップジン M(To
psin M)”、第1201〜1203頁] 5.ベノミル[“ベンレート(Benlate)”、第
100〜102頁] 6.カルベンダジム[“バビスチン(Bavisti
n)”、第182〜184頁] 7.チアベンダゾール[“メルテクト(Mertec
t)”、第1183〜1185頁] C.カーバメート系化合物 8.ジエトフェンカルブ[“スミコ(Sumic
o)”、第386〜387頁] これらの殺菌剤は、灰色かび病に対して優れた効果を示
すが、繰り返し使用した場合に薬剤耐性菌が出現し、効
力の低下を来すという問題がある。On the other hand, component II is a known compound selected from dicarboximide compounds, benzimidazole compounds, and carbamate compounds.
["Product name (English name)", page], and the page means [The Pesticide Manual (The Pesticide Manual).
Manual), 11th edition, The BritishC
rop Protection Council, 19
1997]. A. Dicarboximide compounds 1. Procymidone [“Sumilex
x) ", pp. 1003-1004] 2. Vinclozolin [" Ronilan "
n) ", pp. 1267-1269] 3. Iprodione [" Rovral ",
724 to 726]. 3. Benzimidazole compounds Thiophanate methyl [“Topzine M (To
psin M) ", pp. 1201-1203] 5. Benomyl [" Benlate ", pp. 100-102] 6. Carbendazim [" Babistin "
n) ", pp. 182-184] 7. Thiabendazole [" Mertec "
t) ", pages 1183 to 1185] C. Carbamate-based compounds 8. Dietofencarb [" Sumic
o) ", pp. 386-387] These fungicides exhibit an excellent effect on gray mold, but when used repeatedly, drug-resistant bacteria appear, resulting in a problem of reduced efficacy. is there.
【0005】例えば、ベンズイミダゾール系の殺菌剤
は、殺菌スペクトラムが広く、灰色かび病に対しても優
れた効果を示すが、1970年代に入って耐性菌が出現
し、大幅な効力低下を引き起こした。これに替わるもの
としてジカルボキシイミド系の殺菌剤が注目を浴びた
が、1980年代に入ってジカルボキシイミド系の薬剤
に対しても耐性菌が出現している。更に、1990年代
にベンズイミダゾール耐性菌に対して効果のあるジエト
フェンカルブが開発され、単剤、混剤として使用されて
いるが、現在、本剤に対する耐性菌も報告されており、
灰色かび病耐性菌の防除対策はわが国のみならず世界的
にも大きな問題となっている。[0005] For example, benzimidazole fungicides have a broad germicidal spectrum and show an excellent effect against gray mold, but resistant bacteria emerged in the 1970's, causing a significant decrease in efficacy. . As a substitute for this, a dicarboximide-based bactericide has attracted attention, but in the 1980's, resistant bacteria have emerged even for a dicarboximide-based drug. Further, in the 1990's, dietofencarb, which is effective against benzimidazole-resistant bacteria, was developed and used as a single agent or as a mixture. Currently, resistant bacteria against this drug have also been reported.
Control measures against gray mold resistant bacteria have become a major problem not only in Japan but also worldwide.
【0006】[0006]
【発明が解決しようとする課題】従って、本発明は、成
分Iのチオフェン誘導体の一つと成分IIのジカルボキ
シイミド系化合物、ベンズイミダゾール系化合物、カー
バメート系化合物のうちの一つとの少なくとも二種の有
効成分を含有し、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。Accordingly, the present invention provides at least two types of thiophene derivatives of component I and one of dicarboximide compounds, benzimidazole compounds and carbamate compounds of component II. An object of the present invention is to provide a composition for controlling plant diseases which contains an active ingredient and has a synergistically enhanced action.
【0007】[0007]
【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のジカルボキシイミド系化合物、ベンズイミダゾー
ル系化合物、カーバメート系化合物のうちのすくなくと
も一つの成分と成分Iの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、特に灰色かび病等
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. As a result, surprisingly, among the dicarboxyimide-based compounds, benzimidazole-based compounds, and carbamate-based compounds of Component II, A composition comprising a mixture of at least one component and one of the thiophene derivatives of component I shows an enhanced synergistic effect on the infection of a wide range of plant diseases, in particular diseases such as gray mold, and therefore the solution of the above-mentioned problems The present invention was found to be satisfactory, and the present invention was completed.
【0008】即ち本発明は、少なくとも2種の有効成分
を有し、病害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(化3)[0008] That is, the present invention is a plant protection composition having at least two kinds of active ingredients and having a synergistic effect against disease infection.
【0009】[0009]
【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、メチルチオ基、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
1〜12の直鎖または分岐のアルキル基、炭素数1〜1
2の直鎖または分岐のハロゲノアルキル基、炭素数2〜
10の直鎖または分岐のアルケニル基、炭素数2〜10
の直鎖または分岐のハロゲノアルケニル基、炭素数2〜
10のアルキルチオアルキル基、炭素数2〜10のアル
キルオキシアルキル基、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4)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 methylthio group, a methylsulfoxy group, a methylsulfonyl group, a cyano group, an acetyl group, R represents a linear or branched alkyl group having 1 to 12 carbon atoms, a nitro group, an alkoxycarbonyl group or an amino group;
2 straight-chain or branched halogenoalkyl groups, having 2 to 2 carbon atoms
10 linear or branched alkenyl groups, having 2 to 10 carbon atoms
A straight-chain or branched halogenoalkenyl group having 2 to 2 carbon atoms
An alkylthioalkyl group having 10 carbon atoms, an alkyloxyalkyl group having 2 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms which may be substituted with an alkyl group having 1 to 4 carbon atoms,
A halogeno-substituted cycloalkyl group having 3 to 10 carbon atoms which may be substituted with an alkyl group having 1 to 4 carbon atoms, or 1 to 3
A phenyl group which may be substituted by three substituents, wherein the substituent of the phenyl group is a hydrogen atom, having 1 to 4 carbon atoms;
Alkyl group, alkenyl group having 2 to 4 carbon atoms, 2 carbon atoms
Alkynyl group of 4 to 4, cycloalkyl group of 3 to 6 carbon atoms, alkoxy group of 1 to 4 carbon atoms, halogenoalkoxy group of 1 to 4 carbon atoms, alkylthio group of 1 to 4 carbon atoms, 1 to 4 carbon atoms Alkylsulfoxy group, alkylsulfonyl group having 1 to 4 carbon atoms, halogen atom, cyano group, acyl group having 2 to 4 carbon atoms, alkoxycarbonyl group having 2 to 4 carbon atoms, amino group, or 1 to 3 carbon atoms An amino group substituted with an alkyl group, R and -NHCOAr are adjacent to each other, and Ar is represented by the following (A1) to (A8)
(Formula 4)
【0010】[0010]
【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はジカルボキシイミド系化
合物、ベンズイミダゾール系化合物、カーバメート系化
合物のうちの少なくとも一つを含有する組成物に関す
る。Embedded image (Wherein, R1 is a trifluoromethyl group, a difluoromethyl group, a methyl group, an ethyl group, a chlorine atom, a bromine atom or an iodine atom, and R2 is a hydrogen atom, a methyl group, a trifluoromethyl group or an amino group, n is an integer of 0 to 2)], and the component II is at least one of a dicarboximide compound, a benzimidazole compound, and a carbamate compound. And a composition containing
【0011】本発明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
に病害を防除できる。また、本剤は、灰色かび病に対す
る相乗効果のほか、うどんこ病、赤さび病等に対しても
効果を示す点は、大きなメリットである。By using the composition of the present invention, disease can be effectively controlled with an unexpectedly small amount of the active ingredient as compared with a conventional method. In addition to the synergistic effect on gray mold, this drug is also a significant merit in that it shows an effect on powdery mildew, red rust and the like.
【0012】[0012]
【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
F3 またはMe基であり、R2 がMe基;Arが(A
2)で、R1 がCF3 またはCHF2 基;Arが(A
3)で、R1 はMe基であり、R2 は水素原子またはM
e基;Arが(A4)で、R1 はMe基であり、nは0
〜1;Arが(A5)であり、R1 は塩素原子;Arが
(A6)または(A7);Arが(A8)で、R1 がM
e基であり、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い
てもよい炭素数4〜8のシクロアルキル基で表される化
合物である。特に好ましいものは、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 基であ
り、R3 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
表される化合物である。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
F 3 or a Me group, R 2 is a Me group; Ar is (A
2) wherein R 1 is a CF 3 or CHF 2 group; Ar is (A
In 3), R1 is a Me group, and R2 is a hydrogen atom or M
e group; Ar is (A4), R1 is Me group, and n is 0
Ar is (A5), R1 is a chlorine atom; Ar is (A6) or (A7); Ar is (A8), and R1 is M
e is a group, and R is represented by a linear or branched alkyl group having 4 to 8 carbon atoms, or a cycloalkyl group having 4 to 8 carbon atoms which may be substituted with an alkyl group having 1 to 4 carbon atoms. Compound. Particularly preferred are those wherein Ar is (A1)
R1 is a CF 3 or Me group; R2 is a Me group; Ar
A There (A2), R1 is CF 3 or CHF 2 group, R3 is a hydrogen atom, R is a linear or branched alkyl group having 4-8 carbon atoms or an alkyl group having 1 to 4 carbon atoms, And a compound represented by a cycloalkyl group having 4 to 8 carbon atoms which may be substituted.
【0013】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[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[Rが1,3
−ジメチルブチル基であり、ArがA2(R1=C
F3)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[Rが1,3−ジメチルブチル基であり、A
r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[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
[Rが1,3−ジメチルブチル基であり、ArがA6の
場合] 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 oryzae)、紋枯病
(Rhizoctonia solani)、ごま葉枯病(Cochliobolus miya
beanus)、馬鹿苗病(Gibberella fujikuroi);ムギ類の
うどんこ病(Erysiphe graminis f.sp.hordei; f.sp.tri
tici)、さび病(Puccinia striiformis; P. graminis;
P.recondita; P.hordei)、斑葉病(Pyrenophora gramine
a)、網斑病(Pyrenophora teres)、赤かび病(Gibberella
zeae)、雪腐病(Typhula sp.; Micronectriella nivali
s)、裸黒穂病(Ustilago tritici; U.nuda)、なまぐさ黒
穂病(Tilletia caries)、眼紋病(Pseudocercosporella
herpotrichoides)、株腐病(Rhizoctonia cerealis)、雲
形病(Rhynchosporium secalis)、葉枯病(Septoria trit
ici)、ふ枯病(Leptosphaeria nodorum);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 ampelina)、晩腐病(Glom
erella cingulata);リンゴのうどんこ病(Podosphaera
leucotricha)、黒星病(Venturia inaequalis)、斑点落
葉病(Alternaria mali)、赤星病(Gymnosporangium yama
dae)、モニリア病(Sclerotinia mali)、腐らん病(Valsa
mali);ナシの黒斑病(Alternaria kikuchiana)、黒星
病(Venturia nashicola)、赤星病(Gymnosporangium har
aeanum)、輪紋病(Physalospora piricola);モモの灰星
病(Sclerotinia cinerea)、黒星病(Cladosporium carpo
philum)、フォモプシス腐敗病(Phomopsis sp.);カキの
炭そ病(Gloeosporium kaki)、落葉病(Cercospora kaki;
Mycosphaerella nawae)、うどんこ病(Phyllactinia ka
kikora);キュウリのべと病(Pseudoperonospora cubens
is)、ウリ類のうどんこ病(Sphaerothecafuliginea)、炭
そ病(Colletotrichum lagenarium)、つる枯病(Mycospha
erella melonis);トマトの輪紋病(Alternaria solan
i)、葉かび病(Cladosporium fulvam)、疫病(Phytophtho
ra infestans);ナスのうどんこ病(Erysiphe cichoraco
rum)、すすかび病(Mycovellosiella nattrassii); ア
ブラナ科野菜の黒斑病(Alternaria japonica)、白斑病
(Cercosporella brassicae);ネギのさび病(Puccinia a
llii)、黒斑病(Alternaria porri); ダイズの紫斑病(C
ercospora kikukuchii)、黒とう病(Elsinoe glycinne
s)、黒点病(Diaporthe phaseololum);インゲンの炭そ
病(Colletotrichum lindemuthianum);ラッカセイの黒
渋病(Mycosphaerella personatum)、褐斑病(Cercospora
arachidicola);エンドウのうどんこ病(Erysiphe pis
i)、べと病(Peronospora pisi);ジャガイモの夏疫病(A
lternaria solani)、黒あざ病(Rhizoctonia solani)、
疫病(Phytophthora infestans);ソラマメのべと病(Per
onospora viciae)、疫病(Phytophthora nicotianae);
チャの網もち病(Exobasidium reticulatum)、白星病(El
sinoe leucospila)、炭そ病(Colletotrichum theae-si
nensis);タバコの赤星病(Alternaria longipes)、うど
んこ病(Erysiphe cichoracearum)、 炭そ病(Colletotri
chum tabacum)、疫病(Phytophthora parasitica);テン
サイの褐斑病(Cercospora beticola); バラの黒星病(D
iplocarpon rosae)、うどんこ病(Sphaerotheca pannos
a)、疫病(Phytophthora megasperma); キクの褐斑病(S
eptoria chrysanthemi-indici)、白さび病(Puccinia ho
riana);イチゴのうどんこ病(Sphaerotheca humuli)、
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 sclerot
iorum);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、灰色か
び病等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 following are some specific examples of the compound represented by Component I. Compound No. 1: N- {2- (1,3-dimethylbutyl) -3-thienyl} -2,4-dimethylthiazole-
5-Carboxamide [when R is a 1,3-dimethylbutyl group and Ar is A1 (R1 = Me, R2 = Me)] Compound No. 2: N- {2- (1,3-dimethylbutyl) -3-thienyl} -3-trifluoromethyl-1-
Methylpyrazole-4-carboxylic acid amide [R is 1,3
A dimethylbutyl group, and Ar is A2 (R1 = C
F 3 )] Compound No. 3: N- {2- (1,3-dimethylbutyl) -3-thienyl} -2-methylfuran-3-carboxylic acid amide [R is a 1,3-dimethylbutyl group Yes, A
When r is A3 (R1 = Me, R2 = H)] Compound No. 4: N- {2- (1,3-dimethylbutyl) -3-thienyl} -3-methylthiophen-2-carboxylic acid amide [R Is a 1,3-dimethylbutyl group and Ar is A4 (R1 = Me, n = 0)] Compound No. 5: N- {2- (1,3-dimethylbutyl) -3-thienyl} -2 -Chloronicotinamide
[When R is a 1,3-dimethylbutyl group and Ar is A6] The composition of the present invention is effective against the following types of plant diseases: rice blast ( Pyricularia oryzae ), herb disease
( Rhizoctonia solani ), sesame leaf blight ( Cochliobolus miya)
beanus), bakanae (Gibberella fujikuroi); wheat and barley powdery mildew (Erysiphe graminis f.sp. hordei; f.sp. tri
tici ), rust ( Puccinia striiformis ; P. graminis ;
P. recondita ; P. hordei) , leaf spot disease ( Pyrenophora gramine )
a ), Nettle spot (Pyrenophora teres ), Fusarium head blight ( Gibberella
zeae ), snow rot ( Typhula sp .; Micronectriella nivali
s), loose smut (Ustilago tritic i;. U nuda ), fishy smut (Tilletia caries), Memonbyo (Pseudocercosporella
herpotrichoides), stock rot (Rhizoctonia cerealis), scald (Rhynchosporium secalis), leaf blight (Septoria trit
ici ), Fusarium wilt ( Leptosphaeria nodorum ); Botrytis , such as kidney bean, cucumber, tomato, strawberry, grape, potato, soybean, cabbage, eggplant, lettuce
cinerea ); Grape downy mildew ( Plasmopora viticola ), rust ( Phakopsora ampelopsidis ), powdery mildew ( Uncinula
necator), sphaceloma disease (Elsinoe ampelina), ripe rot (Glom
erella cingulata ); Powdery mildew of apple ( Podosphaera)
leucotricha ), scab ( Venturia inaequalis ), spot leaf rot ( Alternaria mali ), scab ( Gymnosporangium yama)
dae ), Monilia disease ( Sclerotinia mali ), rot ( Valsa
mali ); Pear black spot ( Alternaria kikuchiana ), black scab ( Venturia nashicola ), scab ( Gymnosporangium har
aeanum ), ring spot ( Physalospora piricola ); peach rot ( Sclerotinia cinerea ), scab ( Cladosporium carpo)
philum), Phomopsis rot (Phomopsis sp);. oysters of anthracnose (Gloeosporium kaki), deciduous disease (Cercospora kaki;
Mycosphaerella nawae ), powdery mildew ( Phyllactinia ka
kikora ); downy mildew of cucumber ( Pseudoperonospora cubens
is ), powdery mildew of cucumber ( Sphaerothecafuliginea ), anthracnose ( Colletotrichum lagenarium ), vine blight ( Mycospha
erella melonis ); Tomato ring spot ( Alternaria solan)
i ), leaf mold ( Cladosporium fulvam ), plague ( Phytophtho
ra infestans ); powdery mildew of eggplant ( Erysiphe cichoraco
rum ), scab ( Mycovellosiella nattrassii ); Black spot of cruciferous vegetables ( Alternaria japonica ), white spot
( Cercosporella brassicae ); Rust on green onion ( Puccinia a
llii ), black spot ( Alternaria porri ); soybean purpura ( C
ercospora kikukuchii ), black rot ( Elsinoe glycinne)
s ), Black spot ( Diaporthe phaseololum ); Bean anthracnose ( Colletotrichum lindemuthianum ); Peanut black spot ( Mycosphaerella personatum ), Brown spot ( Cercospora )
arachidicola ); Pea powdery mildew ( Erysiphe pis
i ), downy mildew ( Peronospora pisi ); summer blight of potato ( A
lternaria solani ), black bruise ( Rhizoctonia solani ),
Phytophthora infestans ; downy mildew of broad bean ( Per
onospora viciae ), plague ( Phytophthora nicotianae );
Tea net rot ( Exobasidium reticulatum ), scab ( El
sinoe leucospila ), anthracnose ( Colletotrichum theae-si)
nensis); Tobacco scab ( Alternaria longipes ), powdery mildew ( Erysiphe cichoracearum ), anthracnose ( Colletotri
chum tabacum ), plague ( Phytophthora parasitica ); sugar beet brown spot ( Cercospora beticola ); rose scab ( D
iplocarpon rosae ), powdery mildew ( Sphaerotheca pannos)
a ), plague ( Phytophthora megasperma ); chrysanthemum spot of chrysanthemum ( S
eptoria chrysanthemi - indici ), white rust ( Puccinia ho
riana ); strawberry powdery mildew ( Sphaerotheca humuli ),
Phytophthora nicotianae (S clerotinia sclerot)
iorum ); citrus black spot ( Diaporthe citri ); carrot black leaf spot ( Alternaria dauci ) and the like. Among them, it has a synergistically enhanced effect on gray mold and the like. Such a potentiating effect was not to be expected from the sum of the effects of the individual active ingredients.
【0014】本発明の殺菌剤組成物において、成分Iの
置換チオフェン誘導体と成分IIのジカルボキシイミド
系化合物、ベンズイミダゾール系化合物、カーバメート
系化合物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0.0
1〜50重量部、好ましくは0.01〜10重量部、よ
り好ましくは0.02〜5重量部の範囲内である。In the fungicide composition of the present invention, the mixing ratio of the substituted thiophene derivative of the component I and the dicarboximide compound, benzimidazole compound and the carbamate compound of the component II is not particularly limited. The amount of the compound of the component II was 0.0 to 1 part by weight of the compound.
It is in the range of 1 to 50 parts by weight, preferably 0.01 to 10 parts by weight, more preferably 0.02 to 5 parts by weight.
【0015】本組成物は、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 may be applied directly as a mixture containing the two active ingredients, separately or simultaneously with the individual active ingredients, or applied one after the other. Furthermore,
For the mixture containing the active ingredients, the concentrated composition containing the two active ingredients may be diluted with water, or a mixture may be prepared at the time of use from the two concentrates containing the individual active ingredients, and this may be used. It 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.
【0016】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。The carrier as used herein refers to a synthetic or natural inorganic or organic substance incorporated to assist in reaching the active ingredient to 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.
【0017】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。Examples of the solid carrier include clays such as montmorillonite and kaolinite; inorganic substances such as diatomaceous earth, terra alba, talc, vermiculite, gypsum, calcium carbonate, silica gel, and ammonium sulfate; 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.
【0018】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。As the liquid carrier, toluene, xylene,
Aromatic hydrocarbons such as 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 dimethylsulfoxide, and water.
【0019】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.
【0020】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; Natural or synthetic phospholipids of cephalin or lecithin series 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.
【0021】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。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.
【0022】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 adjuvant is from 0 to 80% by weight,
The content of the carrier is an amount obtained by subtracting the content of the active ingredient compound and the content of the auxiliary from 100% by weight.
【0023】本発明組成物の施用方法としては種子処
理、茎葉散布、土壌灌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50〜2,000gが適当であ
り、望ましくはヘクタール当り100〜1、000g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200〜20,00
0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。The method of applying the composition of the present invention includes seed treatment, foliage application, soil irrigation, and the like, and any application method generally used by those skilled in the art can exert sufficient effects. The application amount and application concentration vary depending on the target crop, the target disease, the degree of occurrence of the disease, the compound dosage form, the application method, various environmental conditions, and the like. However, when spraying, the active ingredient amount is 50 to 2,000 g per hectare. Is suitable, desirably from 100 to 1,000 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 0 is appropriate, preferably a factor of 500 to 5,000. In the case of seed disinfection, the amount of the fungicide mixture used is 0.001 to 50 g, preferably 0.01 to 10 g per kg of seed.
【0024】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。The composition of the present invention may be used in a mixture with other pesticides such as fungicides, insecticides, acaricides, nematicides, herbicides and plant growth regulators, soil conditioners or fertilizers. However, a mixed preparation with these is also possible.
【0025】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.
【0026】[0026]
【実施例】製剤例 1(水和剤) 化合物番号1:15部、イプロジオン:30部、リグニ
ンスルホン酸ナトリウム:10部、アルキルナフタレン
スルホン酸ナトリウム:5部、ホワイトカーボン:10
部および珪藻土:30部を均一に粉砕混合して水和剤を
得た。Examples Formulation Example 1 (Wettable powder) Compound No. 1:15 parts, iprodione: 30 parts, sodium ligninsulfonate: 10 parts, sodium alkylnaphthalenesulfonate: 5 parts, white carbon: 10
Parts and diatomaceous earth: 30 parts were uniformly ground and mixed to obtain a wettable powder.
【0027】製剤例 2(水和剤) 化合物番号2:20部、プロシミドン:30部、リグニ
ンスルホン酸ナトリウム:1部、アルキルベンゼンスル
ホン酸ナトリウム:2部および珪藻土:47部を粉砕混
合して、水和剤を得た。Formulation Example 2 (Wettable powder) Compound No. 2: 20 parts, procymidone: 30 parts, sodium ligninsulfonate: 1 part, sodium alkylbenzenesulfonate: 2 parts, and diatomaceous earth: 47 parts are pulverized and mixed. A sum was obtained.
【0028】製剤例 3(フロアブル剤) 化合物番号2:20部、プロシミドン:30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:44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: 20 parts, procymidone: 30 parts, propylene glycol: 3 parts, sodium ligninsulfonate: 2 parts, dioctyl sulfosuccinate sodium salt: 1 part, and water: 44 The part was wet-pulverized with a sand grinder to obtain a flowable agent.
【0029】製剤例 4(水和剤) 化合物番号2:20部、ベノミル:30部、リグニンス
ルホン酸ナトリウム:1部、アルキルベンゼンスルホン
酸ナトリウム:2部および珪藻土:47部を粉砕混合し
て、水和剤を得た。Formulation Example 4 (Wetting powder) Compound No. 2: 20 parts, benomyl: 30 parts, sodium ligninsulfonate: 1 part, sodium alkylbenzenesulfonate: 2 parts, and diatomaceous earth: 47 parts were pulverized and mixed. A sum was obtained.
【0030】製剤例 5(水和剤) 化合物番号3:20部、チオファネート メチル:20
部、リグニンスルホン酸カルシウム:3部、ラウリル硫
酸ナトリウム:2部および珪藻土:55部を粉砕混合し
て、水和剤を得た。Formulation Example 5 (Wettable powder) Compound No. 3:20 parts, thiophanate methyl: 20
, Calcium lignin sulfonate: 3 parts, sodium lauryl sulfate: 2 parts and diatomaceous earth: 55 parts were pulverized and mixed to obtain a wettable powder.
【0031】製剤例 6(フロアブル剤) 化合物番号2:20部、チオファネート メチル:30
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:44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 6 (Flowable agent) Compound No. 2: 20 parts, thiophanate methyl: 30
Parts, propylene glycol: 3 parts, sodium lignin sulfonate: 2 parts, dioctyl sulfosuccinate sodium salt: 1 part, and water: 44 parts were wet-pulverized with a sand grinder to obtain a flowable agent.
【0032】製剤例 7(フロアブル剤) 化合物番号2:25部、ジエトフェンカルブ: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:49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 7 (Floable agent) Compound No. 2: 25 parts, Dietofencarb: 20 parts,
Polyoxyethylene sorbitan monooleate: 3 parts,
Carboxymethyl cellulose: 3 parts and water: 49 parts were wet-pulverized with a sand grinder to obtain a flowable agent.
【0033】次に本発明化合物の農園芸用殺菌剤として
の効力を試験例によって説明する。Next, the efficacy of the compound of the present invention as a fungicide for agricultural and horticultural use will be described with reference to test examples.
【0034】試験例1 インゲン灰色かび病防除試験
(1) 温室内で直径7.5cmのプラスチックポットに子葉の
展開まで2本ずつ生育させたインゲン(品種:つるなし
トップクロップ)に、製剤例1に準じて調製した水和剤
を所定濃度に希釈して、4ポット当たり50mlずつ散
布した。薬液が乾いた後PDA培地上で培養した灰色か
び菌(MBC耐性、RS菌)から調製した分生胞子懸濁
液(1×105個/ml)を子葉上に噴霧接種し、20
〜23℃、湿度95%以上の温室に7日間保った。接種
7日後、インゲン1葉当たりに灰色かび病の病斑が占め
る面積を次の指標に従って調査した。結果を第1表(表
1)に示す。Test Example 1 Test for controlling bean gray mold (1) Formulation example 1 was applied to a kidney bean (cultivar: vineless top crop) grown in a greenhouse in a plastic pot having a diameter of 7.5 cm two by two until cotyledons developed. The wettable powder prepared according to the above was diluted to a predetermined concentration, and sprayed 50 ml per 4 pots. After the drug solution was dried, a conidia spore suspension (1 × 10 5 cells / ml) prepared from Botrytis cinerea (MBC resistant, RS bacterium) cultured on a PDA medium was spray-inoculated onto cotyledons and sprayed onto the cotyledon.
It was kept in a greenhouse at 2323 ° C. and a humidity of 95% or more for 7 days. Seven days after the inoculation, the area occupied by the gray mold spot per kidney leaf was examined according to the following index. The results are shown in Table 1 (Table 1).
【0035】 各処理区および無処理区の平均値を発病度とした。[0035] The average value of each treated section and the untreated section was defined as the disease severity.
【0036】防除価(%)=(1−処理区の発病度/無
処理区の発病度)×100Control value (%) = (1−degree of disease in treated group / degree of disease in untreated group) × 100
【0037】[0037]
【表1】 [Table 1]
【0038】試験例2 インゲン灰色かび病防除試験
(2) 温室内で直径7.5cmのプラスチックポットに子葉の
展開まで2本ずつ生育させたインゲン(品種:つるなし
トップクロップ)に、製剤例1に準じて調製した水和剤
を所定濃度に希釈して、4ポット当たり50mlずつ散
布した。薬液が乾いた後PDA培地上で培養した灰色か
び菌(MBC耐性・ジカルボキシイミド系薬剤耐性、R
R菌)から調製した分生胞子懸濁液(1×105個/m
l)を子葉上に噴霧接種し、20〜23℃、湿度95%
以上の温室に7日間保った。接種7日後、インゲン1葉
当たりに灰色かび病の病斑が占める面積を次の指標に従
って調査した。結果を第2表(表2)に示す。Test Example 2 Test for controlling bean gray mold (2) Formulation example 1 was prepared in a greenhouse by growing green beans in a 7.5 cm-diameter plastic pot until cotyledons were developed two by two (cultivar: vineless top crop). The wettable powder prepared according to the above was diluted to a predetermined concentration, and sprayed 50 ml per 4 pots. Gray mold fungi cultured on PDA medium after the drug solution dries (MBC resistant / dicarboximide resistant, R
R.) (1 × 10 5 cells / m)
l) is spray-inoculated on cotyledons, and the temperature is 20 to 23 ° C and the humidity is 95%.
It was kept in the above greenhouse for 7 days. Seven days after the inoculation, the area occupied by the gray mold spot per kidney leaf was examined according to the following index. The results are shown in Table 2 (Table 2).
【0039】 各処理区および無処理区の平均値を発病度とした。[0039] The average value of each treated section and the untreated section was defined as the disease severity.
【0040】防除価(%)=(1−処理区の発病度/無
処理区の発病度)×100Control value (%) = (1−degree of disease in treated group / degree of disease in untreated group) × 100
【0041】[0041]
【表2】 [Table 2]
【0042】[0042]
【発明の効果】本発明は、少なくとも2種の有効成分を
含む殺菌剤組成物であり、広範囲の植物病害、特に灰色
かび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。Industrial Applicability The present invention is a fungicidal composition containing at least two kinds of active ingredients, and has a synergistically enhanced effect on a wide range of plant diseases, especially on gray mold, and therefore, is useful for plant diseases. It is useful as a controlling agent composition.
【0043】このような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、病害の防除ができる。By using such a composition of the present invention, it is possible to control a disease with an unexpectedly small amount of an active ingredient as compared with a conventional method.
───────────────────────────────────────────────────── フロントページの続き (51)Int.Cl.6 識別記号 FI A01N 43/76 A01N 43/76 43/78 43/78 Z 47/18 101 47/18 101C 47/20 47/20 Z 47/34 47/34 D 47/38 47/38 B C (72)発明者 川島 秀雄 千葉県茂原市東郷1144番地 三井化学株式 会社内 (72)発明者 明瀬 智久 千葉県茂原市東郷1144番地 三井化学株式 会社内──────────────────────────────────────────────────の Continued on the front page (51) Int.Cl. 6 Identification code FI A01N 43/76 A01N 43/76 43/78 43/78 Z 47/18 101 47/18 101C 47/20 47/20 Z 47 / 34 47/34 D 47/38 47/38 BC (72) Inventor Hideo Kawashima 1144 Togo, Mobara-shi, Chiba Mitsui Chemicals Co., Ltd. (72) Inventor Tomohisa Akase 1144 Togo, Togo, Mobara-shi, Chiba Mitsui Chemicals Inside
Claims (7)
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(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、メチルチオ基、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
1〜12の直鎖または分岐のアルキル基、炭素数1〜1
2の直鎖または分岐のハロゲノアルキル基、炭素数2〜
10の直鎖または分岐のアルケニル基、炭素数2〜10
の直鎖または分岐のハロゲノアルケニル基、炭素数2〜
10のアルキルチオアルキル基、炭素数2〜10のアル
キルオキシアルキル基、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はジカルボキシイミド系化
合物、ベンズイミダゾール系化合物、カーバメート系化
合物から選ばれる化合物である殺菌剤組成物。1. A plant protection composition having at least two kinds of active ingredients and having a synergistic effect against infection of a disease, wherein the component I is represented by the following formula. 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 methylthio group, a methylsulfoxy group, a methylsulfonyl group, a cyano group, an acetyl group, R represents a linear or branched alkyl group having 1 to 12 carbon atoms, a nitro group, an alkoxycarbonyl group or an amino group;
2 straight-chain or branched halogenoalkyl groups, having 2 to 2 carbon atoms
10 linear or branched alkenyl groups, having 2 to 10 carbon atoms
A straight-chain or branched halogenoalkenyl group having 2 to 2 carbon atoms
An alkylthioalkyl group having 10 carbon atoms, an alkyloxyalkyl group having 2 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms which may be substituted with an alkyl group having 1 to 4 carbon atoms,
A halogeno-substituted cycloalkyl group having 3 to 10 carbon atoms which may be substituted with an alkyl group having 1 to 4 carbon atoms, or 1 to 3
A phenyl group which may be substituted by three substituents, wherein the substituent of the phenyl group is a hydrogen atom, having 1 to 4 carbon atoms;
Alkyl group, alkenyl group having 2 to 4 carbon atoms, 2 carbon atoms
Alkynyl group of 4 to 4, cycloalkyl group of 3 to 6 carbon atoms, alkoxy group of 1 to 4 carbon atoms, halogenoalkoxy group of 1 to 4 carbon atoms, alkylthio group of 1 to 4 carbon atoms, 1 to 4 carbon atoms Alkylsulfoxy group, alkylsulfonyl group having 1 to 4 carbon atoms, halogen atom, cyano group, acyl group having 2 to 4 carbon atoms, alkoxycarbonyl group having 2 to 4 carbon atoms, amino group, or 1 to 3 carbon atoms An amino group substituted with an alkyl group, R and -NHCOAr are adjacent to each other, and Ar is represented by the following (A1) to (A8)
(Chemical formula 2) (Wherein, R1 is a trifluoromethyl group, a difluoromethyl group, a methyl group, an ethyl group, a chlorine atom, a bromine atom or an iodine atom, and R2 is a hydrogen atom, a methyl group, a trifluoromethyl group or an amino group, n is an integer of 0 to 2)], and the component II is a compound selected from a dicarboximide-based compound, a benzimidazole-based compound, and a carbamate-based compound. Certain fungicide compositions.
Rは炭素数3〜10の直鎖または分岐のアルキル基、炭
素数3〜10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、
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3〜10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,
R is a linear or branched alkyl group having 3 to 10 carbon atoms, a linear or branched halogenoalkyl group having 3 to 10 carbon atoms,
A straight-chain or branched alkenyl group having 3 to 10 carbon atoms, a straight-chain or branched halogenoalkenyl group having 3 to 10 carbon atoms,
The composition according to claim 1, which is a cycloalkyl group having 3 to 10 carbon atoms which may be substituted with an alkyl group having 1 to 4 carbon atoms.
り、R1 がCF3またはMe基であり、R2がMe基であ
る請求項2記載の組成物。3. The composition according to claim 2, wherein in component I, Ar is (A1), R1 is CF 3 or Me group, and R2 is Me group.
り、R1 がCF3またはCHF2基である請求項2記載の
組成物。4. The composition according to claim 2, wherein in component I, Ar is (A2) and R 1 is a CF 3 or CHF 2 group.
系化合物がプロシミドン、ビンクロゾリン、イプロジオ
ンである請求項2、請求項3または請求項4記載の組成
物。5. The composition according to claim 2, wherein in the component II, the dicarboximide compound is procymidone, vinclozolin, or iprodione.
系化合物がチオファネートメチル、ベノミル、、カルベ
ンダゾール、チアベンダゾールである請求項2、請求項
3または請求項4記載の組成物。6. The composition according to claim 2, wherein the benzimidazole compound in Component II is thiophanate methyl, benomyl, carbendazole, or thiabendazole.
物がジエトフェンカルブである請求項2、請求項3また
は請求項4記載の組成物。7. The composition according to claim 2, wherein the carbamate compound in component II is dietofencarb.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP11558498A JP3824421B2 (en) | 1998-04-24 | 1998-04-24 | Plant disease control composition |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP11558498A JP3824421B2 (en) | 1998-04-24 | 1998-04-24 | Plant disease control composition |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH11302111A true JPH11302111A (en) | 1999-11-02 |
| JP3824421B2 JP3824421B2 (en) | 2006-09-20 |
Family
ID=14666218
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP11558498A Expired - Lifetime JP3824421B2 (en) | 1998-04-24 | 1998-04-24 | Plant disease control composition |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP3824421B2 (en) |
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