JPWO2009022746A1 - 含窒素複素環化合物および有害生物防除剤 - Google Patents
含窒素複素環化合物および有害生物防除剤 Download PDFInfo
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- JPWO2009022746A1 JPWO2009022746A1 JP2009528158A JP2009528158A JPWO2009022746A1 JP WO2009022746 A1 JPWO2009022746 A1 JP WO2009022746A1 JP 2009528158 A JP2009528158 A JP 2009528158A JP 2009528158 A JP2009528158 A JP 2009528158A JP WO2009022746 A1 JPWO2009022746 A1 JP WO2009022746A1
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- UBCKGWBNUIFUST-YHYXMXQVSA-N tetrachlorvinphos Chemical compound COP(=O)(OC)O\C(=C/Cl)C1=CC(Cl)=C(Cl)C=C1Cl UBCKGWBNUIFUST-YHYXMXQVSA-N 0.000 description 1
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- WOSNCVAPUOFXEH-UHFFFAOYSA-N thifluzamide Chemical compound S1C(C)=NC(C(F)(F)F)=C1C(=O)NC1=C(Br)C=C(OC(F)(F)F)C=C1Br WOSNCVAPUOFXEH-UHFFFAOYSA-N 0.000 description 1
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- BAKXBZPQTXCKRR-UHFFFAOYSA-N thiodicarb Chemical compound CSC(C)=NOC(=O)NSNC(=O)ON=C(C)SC BAKXBZPQTXCKRR-UHFFFAOYSA-N 0.000 description 1
- QGHREAKMXXNCOA-UHFFFAOYSA-N thiophanate-methyl Chemical compound COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC QGHREAKMXXNCOA-UHFFFAOYSA-N 0.000 description 1
- QSOHVSNIQHGFJU-UHFFFAOYSA-L thiosultap disodium Chemical compound [Na+].[Na+].[O-]S(=O)(=O)SCC(N(C)C)CSS([O-])(=O)=O QSOHVSNIQHGFJU-UHFFFAOYSA-L 0.000 description 1
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- OBZIQQJJIKNWNO-UHFFFAOYSA-N tolclofos-methyl Chemical group COP(=S)(OC)OC1=C(Cl)C=C(C)C=C1Cl OBZIQQJJIKNWNO-UHFFFAOYSA-N 0.000 description 1
- WPALTCMYPARVNV-UHFFFAOYSA-N tolfenpyrad Chemical compound CCC1=NN(C)C(C(=O)NCC=2C=CC(OC=3C=CC(C)=CC=3)=CC=2)=C1Cl WPALTCMYPARVNV-UHFFFAOYSA-N 0.000 description 1
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- YWSCPYYRJXKUDB-KAKFPZCNSA-N tralomethrin Chemical compound CC1(C)[C@@H](C(Br)C(Br)(Br)Br)[C@H]1C(=O)O[C@H](C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 YWSCPYYRJXKUDB-KAKFPZCNSA-N 0.000 description 1
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- DQJCHOQLCLEDLL-UHFFFAOYSA-N tricyclazole Chemical compound CC1=CC=CC2=C1N1C=NN=C1S2 DQJCHOQLCLEDLL-UHFFFAOYSA-N 0.000 description 1
- ONCZDRURRATYFI-TVJDWZFNSA-N trifloxystrobin Chemical compound CO\N=C(\C(=O)OC)C1=CC=CC=C1CO\N=C(/C)C1=CC=CC(C(F)(F)F)=C1 ONCZDRURRATYFI-TVJDWZFNSA-N 0.000 description 1
- HSMVPDGQOIQYSR-KGENOOAVSA-N triflumizole Chemical compound C1=CN=CN1C(/COCCC)=N/C1=CC=C(Cl)C=C1C(F)(F)F HSMVPDGQOIQYSR-KGENOOAVSA-N 0.000 description 1
- 125000005034 trifluormethylthio group Chemical group FC(S*)(F)F 0.000 description 1
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 1
- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 description 1
- RROQIUMZODEXOR-UHFFFAOYSA-N triforine Chemical compound O=CNC(C(Cl)(Cl)Cl)N1CCN(C(NC=O)C(Cl)(Cl)Cl)CC1 RROQIUMZODEXOR-UHFFFAOYSA-N 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- JARYYMUOCXVXNK-IMTORBKUSA-N validamycin Chemical compound N([C@H]1C[C@@H]([C@H]([C@H](O)[C@H]1O)O[C@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O)CO)[C@H]1C=C(CO)[C@H](O)[C@H](O)[C@H]1O JARYYMUOCXVXNK-IMTORBKUSA-N 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 230000003612 virological effect Effects 0.000 description 1
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- 235000010493 xanthan gum Nutrition 0.000 description 1
- DUBNHZYBDBBJHD-UHFFFAOYSA-L ziram Chemical compound [Zn+2].CN(C)C([S-])=S.CN(C)C([S-])=S DUBNHZYBDBBJHD-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/80—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
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Abstract
Description
本願は、2007年8月10日に出願された日本国特許出願第2007−208855号、及び2007年12月26日に出願された日本国特許出願第2007−333470号に対して優先権を主張し、その内容をここに援用する。
しかしながら、この文献には、本発明化合物は記載されていない。
Zは、無置換もしくは置換基を有するアリール基、無置換もしくは置換基を有する複素環基、無置換もしくは置換基を有するアルキル基、無置換もしくは置換基を有するアルケニル基、または無置換もしくは置換基を有するアルキニル基を表す。
Qは、下記式(I’)で示される基を表す。
Yは、ニトロ基、水酸基、メルカプト基、ハロゲン原子、無置換もしくは置換基を有するアミノ基、又は有機基を表す。
nは0〜3の整数を表し、nが2以上のとき、複数のYは互いに同一であっても、相異なっていてもよい。2つのYが隣接する場合には、2つのYが一緒になって結合して、4〜6員環を形成してもよい。
Dは、置換基X以外の置換基を有さない、または、有する、5〜8員環の炭化水素環基または複素環基を表す。
n1は、0〜2のいずれかの整数を表し、n1が2の場合、2つのXは、同一であっても、相異なっていてもよい。
Xは、下記式(II)−1または式(II)−2で表される官能基を表す。
R1とR2は、各々独立して、水素原子、ニトロ基、水酸基、メルカプト基、無置換もしくは置換基を有するアミノ基、又は有機基を表す。R1とR2は、一緒になって結合して3〜8員環を形成していてもよい。あるいは、R1とR2は、一緒になって二重結合を形成し、下記式:
R11は、水素原子、水酸基、メルカプト基、無置換もしくは置換基を有するアミノ基、又は有機基を表す。
前記式(II)−1中、R1が、式(III)
で示される基のいずれか一つを表すことが好ましい。
本発明の第3の態様は、前記本発明の第1の態様の含窒素複素環化合物若しくはその塩の少なくとも一種を有効成分として含有する殺ダニ剤に関する。
本発明の第4の態様は、前記本発明の第1の態様の含窒素複素環化合物もしくはその塩の少なくとも一種を有効成分として含有する衛生害虫駆除剤に関する。
1)式(I)で表される含窒素複素環化合物又はその塩
本発明の第1の態様は、下記式(I)で表される含窒素複素環化合物(以下、「本発明の含窒素複素環化合物」ということがある。)又はその塩に関する。
前記ハロゲン原子としては、フッ素原子、塩素原子、臭素原子等が挙げられる。
前記無置換もしくは置換基を有するアミノ基としては、アミノ基;メチルアミノ基、エチルアミノ基、i−プロピルアミノ基等のモノC1〜C6アルキルアミノ基;ジメチルアミノ基、ジエチルアミノ基等のジC1〜C6アルキルアミノ基;アセチルアミノ基、ベンゾイルアミノ基等のアシルアミノ基;フェニルアミノ基、4−メチルフェニルアミノ基等の無置換もしくは置換基を有するアリールアミノ基;等が挙げられる。
(1)フッ素原子、塩素原子、臭素原子、ヨウ素原子等のハロゲン原子。
(2)メチル基、エチル基、n−プロピル基、i−プロピル基、n−ブチル基、s−ブチル基、i−ブチル基、s−ブチル基、t−ブチル基、n−ペンチル基、n−ヘキシル基等のアルキル基。
(3)シクロプロピル基、シクロブチル基、シクロペンチル基、シクロヘキシル基、シクロヘプチル基等のシクロアルキル基。
(4)メトキシ基、エトキシ基、n−プロポキシ基、イソプロポキシ基、n−ブトキシ基、i−ブトキシ基、s−ブトキシ基、t−ブトキシ基等のアルコキシ基。
(5)ビニル基、1−プロペニル基、2−プロペニル基、1−ブテニル基、2−ブテニル基、3−ブテニル基、1−メチル−2−プロペニル基、2−メチル−2−プロペニル基、1−ペンテニル基、2−ペンテニル基、3−ペンテニル基、4−ペンテニル基、1−メチル−2−ブテニル基、2−メチル−2−ブテニル基、1−ヘキセニル基、2−ヘキセニル基、3−ヘキセニル基、4−ヘキセニル基、5−ヘキセニル基等のアルケニル基。
(6)2−シクロプロペニル基、2−シクロペンテニル基、3−シクロヘキセニル基、4−シクロオクテニル基等のシクロアルケニル基。
(7)ビニルオキシ基、アリルオキシ基、1−プロペニルオキシ基、2−ブテニルオキシ基等のアルケニルオキシ基。
(8)エチニル基、1−プロピニル基、2−プロピニル基、1−ブチニル基、2−ブチニル基、3−ブチニル基、1−メチル−2−プロピニル基、2−メチル−3−ブチニル基、1−ペンチニル基、2−ペンチニル基、3−ペンチニル基、4−ペンチニル基、1−メチル−2−ブチニル基、2−メチル−3−ペンチニル基、1−ヘキシニル基、1,1−ジメチル−2−ブチニル基等のアルキニル基。
(9)エチニルオキシ基、プロパルギルオキシ基等のアルキニルオキシ基。
(10)フェニル基、1−ナフチル基、2−ナフチル基等のアリール基。
(11)フェノキシ基、1−ナフトキシ基等のアリールオキシ基。
(12)ベンジル基、フェネチル基等のアラルキル基。
(13)ベンジルオキシ基、フェネチルオキシ基等のアラルキルオキシ基。
(14)ホルミル基、アセチル基、プロピオニル基、ベンゾイル基、シクロヘキシルカルボニル基、フタロイル基等のアシル基。
(15)メトキシカルボニル基、エトキシカルボニル基、n−プロポキシカルボニル基、イソプロポキシカルボニル基、n−ブトキシカルボニル基、t−ブトキシカルボニル基等のアルコキシカルボニル基。
(16)カルボキシル基。
(17)水酸基。
(18)クロロメチル基、クロロエチル基、1,2−ジクロロ−n−プロピル基、1−フルオロ−n−ブチル基、パーフルオロ−n−ペンチル基等のハロアルキル基。
2−クロロ−n−プロポキシ基、2,3−ジクロロブトキシ基、トリフルオロメトキシ基等のハロアルコキシ基。
(19)2−クロロ−1−プロペニル基、2−フルオロ−1−ブテニル基等のハロアルケニル基。
(20)4,4−ジクロロ−1−ブチニル基、4−フルオロ−1−ペンチニル基、5−ブロモ−2−ペンチニル基等のハロアルキニル基。
(21)2−クロロ−1−プロペニルオキシ基、3−ブロモ−2−ブテニルオキシ基等のハロアルケニルオキシ基。
(22)3−クロロ−プロパルギル基、3−アイオド−プロパルギル基等のハロアルキニル基。
(23)3−クロロ−プロパルギルオキシ基、3−アイオド−プロパルギルオキシ基等のハロアルキニルオキシ基。
(24)4−クロロフェニル基、4−フルオロフェニル基、2,4−ジクロロフェニル基等のハロアリール基。
(25)4−フルオロフェノキシ基、4−クロロ−1−ナフトキシ基等のハロアリールオキシ基。
(27)メトキシメチル基、エトキシメチル基、1−エトキシエチル基、2−エトキシエチル基等のアルコキシアルキル基。
(28)メトキシメトキシ基、エトキシメトキシ基、1−エトキシエトキシ基、2−エトキシエトキシ基等のアルコキシアルコキシ基。
(29)シアノ基。
(30)イソシアノ基。
(31)ニトロ基。
(32)イソシアナト基。
(33)シアナト基。
(34)アミノ基。
(35)メチルアミノ基、ジメチルアミノ基、ジエチルアミノ基等のアルキルアミノ基。
(36)アニリノ基、ナフチルアミノ基、アントラニルアミノ基等のアリールアミノ基。
(37)ベンジルアミノ基、フェネチルアミノ基等のアラルキルアミノ基。
(38)メチルスルホニルアミノ基、エチルスルホニルアミノ基、n−プロピルスルホニルアミノ基、イソプロピルスルホニルアミノ基、n−ブチルスルホニルアミノ基等のアルキルスルホニルアミノ基。
(39)フェニルスルホニルアミノ基等のアリールスルホニルアミノ基。
(40)ピペラジニルスルホニルアミノ基等のヘテロアリールスルホニルアミノ基。
(41)ホルミルアミノ基、アセチルアミノ基、プロパノイルアミノ基、ブチリルアミノ基、イソプロピルカルボニルアミノ基、ベンゾイルアミノ基等のアシルアミノ基。
(42)メトキシカルボニルアミノ基、エトキシカルボニルアミノ基等のアルコキシカルボニルアミノ基。
(43)フルオロメチルスルホニルアミノ基、クロロメチルスルホニルアミノ基、ブロモメチルスルホニルアミノ基、ジフルオロメチルスルホニルアミノ基、ジクロロメチルスルホニルアミノ基、1,1−ジフルオロエチルスルホニルアミノ基、トリフルオロメチルスルホニルアミノ基、2,2,2−トリフルオロエチルスルホニルアミノ基、ペンタフルオロスルホニルアミノ基等のハロアルキルスルホニルアミノ基。
(44)ビス(メチルスルホニル)アミノ基、ビス(エチルスルホニル)アミノ基、(エチルスルホニル)(メチルスルホニル)アミノ基、ビス(n−プロピルスルホニル)アミノ基、ビス(イソプロピルスルホニル)アミノ基、ビス(n−ブチルスルホニル)アミノ基、ビス(t−ブチルスルホニル)アミノ基等のビス(アルキルスルホニル)アミノ基。
(45)ビス(フルオロメチルスルホニル)アミノ基、ビス(クロロメチルスルホニル)アミノ基、ビス(ブロモメチルスルホニル)アミノ基、ビス(ジクロロメチルスルホニル)アミノ基、ビス(1,1−ジフルオロエチルスルホニル)アミノ基、ビス(トリフルオロメチルスルホニル)アミノ基、ビス(2,2,2−トリフルオロエチル)アミノ基、ビス(ペンタフルオロエチルスルホニル)アミノ基等のビス(ハロアルキルスルホニル)アミノ基。
(46)ヒドラジノ基、N’−フェニルヒドラジノ基、N’−メトキシカルボニルヒドラジノ基、N’−アセチルヒドラジノ基、N’−メチルヒドラジノ基等の無置換もしくは置換ヒドラジノ基。
(47)アミノカルボニル基、ジメチルアミノカルボニル基、フェニルアミノカルボニル基、N−フェニル−N−メチルカルボニル基等の無置換もしくは置換アミノカルボニル基。
(48)ヒドラジノカルボニル基、N’−メチルヒドラジノカルボニル基、N’−フェニルヒドラジノカルボニル基等の無置換もしくは置換ヒドラジノカルボニル基。
(49)N−メチルイミノメチル基、1−N−フェニルイミノエチル基、N−ヒドロキシイミノメチル基、N−メトキシイミノメチル基等の無置換もしくは置換イミノアルキル基。
(50)チオール基。
(51)イソチオシアナト基。
(52)チオシアナト基。
(54)ビニルチオ基、アリルチオ基等のアルケニルチオ基。
(55)エチニルチオ基、プロパルギルチオ基等のアルキニルチオ基。
(56)フェニルチオ基、ナフチルチオ基等のアリールチオ基。
(57)2−ピペリジルチオ基、3−ピリダジルチオ基等のヘテロアリールチオ基。
(58)ベンジルチオ基、フェネチルチオ基等のアラルキルチオ基。
(59)2−ピリジルメチルチオ基、2−フリルメチルチオ基等のヘテロアリールアルキルチオ基。
(60)メチルチオカルボニル基、エチルチオカルボニル基、n−プロピルチオカルボニル基、イソプロピルチオカルボニル基、n−ブチルチオカルボニル基、イソブチルチオカルボニル基、s−ブチルチオカルボニル基、t−ブチルチオカルボニル基等のアルキルチオカルボニル基、
(61)メチルチオメチル基、1−メチルチオエチル基等のアルキルチオアルキル基。
(62)フェニルチオメチル基、1−フェニルチオエチル基等のアリールチオアルキル基。
(63)メチルチオメトキシ基、1−メチルチオエトキシ基等のアルキルチオアルコキシ基。
(64)フェニルチオメトキシ基、1−フェニルチオエトキシ基等のアリールチオアルコキシ基。
(65)メチルスルフィニル基、エチルスルフィニル基、t−ブチルスルフェニル基等のアルキルスルフェニル基。
(66)アリルスルフィニル基等のアルケニルスルフィニル基。
(67)プロパルギルスルフィニル基等のアルキニルスルフィニル基。
(68)フェニルスルフィニル基等のアリールスルフィニル基。
(69)2−ピリジルスルフィニル基、3−ピリジルスルフィニル基等のヘテロアリールスルフィニル基。
(70)ベンジルスルフィニル基、フェネチルスルフィニル基等のアラルキルスルフィニル基。
(71)2−ピリジルメチルスルフィニル基、3−ピリジルメチルスルフィニル基等のヘテロアリールアルキルスルフェニル基。
(72)メチルスルホニル基、エチルスルホニル基、t−ブチルスルホニル基等のアルキルスルホニル基。
(73)アリルスルホニル基等のアルケニルスルホニル基。
(74)プロパルギルスルホニル基等のアルキニルスルホニル基。
(75)フェニルスルホニル基等のアリールスルホニル基。
(76)2−ピリジルスルホニル基、3−ピリジルスルホニル基等のヘテロアリールスルホニル基。
(77)ベンジルスルホニル基、フェネチルスルホニル基等のアラルキルスルホニル基。
(78)2−ピリジルメチルスルホニル基、3−ピリジルメチルスルホニル基等のヘテロアリールアルキルスルホニル基。
(79)フラン−2−イル基、フラン−3−イル基、チオフェン−2−イル基、チオフェン−3−イル基、ピロール−2−イル基、ピロール−3−イル基、オキサゾール−2−イル基、オキサゾール−4−イル基、オキサゾール−5−イル基、チアゾール−2−イル基、チアゾール−4−イル基、チアゾール−5−イル基、イソオキサゾール−3−イル基、イソオキサゾール−4−イル基、イソオキサゾール−5−イル基、イソチアゾール−3−イル基、イソチアゾール−4−イル基、イソチアゾール−5−イル基、イミダゾール−2−イル基、イミダソール−4−イル基、イミダゾール−5−イル基、ピラゾール−3−イル基、ピラゾール−4−イル基、ピラゾール−5−イル基、1,3,4−オキサジアゾール−2−イル基、1,3,4−チアジアゾール−2−イル基、1,2,3−トリアゾール−4−イル基、1,2,4−トリアゾール−3−イル基、1,2,4−トリアゾール−5−イル基等の不飽和複素5員環基。
(80)ピリジン−2−イル基、ピリジン−3−イル基、ピリジン−4−イル基、5−クロロ−3−ピリジル基、3−トリフルオロメチル−2−ピリジル基、ピリダジン−3−イル基、ピリダジン−4−イル基、ピラジン−2−イル基、ピリミジン−5−イル基、1,3,5−トリアジン−2−イル基、1,2,4−トリアジン−3−イル基等の不飽和複素6員環基。
(81)テトラヒドロフラン−2−イル基、テトラヒドロピラン−4−イル基、ピペリジン−3−イル基、ピロリジン−2−イル基、モルホリノ基、ピペリジノ基、N−メチルピペラジノ基、オキサゾリン−2−イル基等の飽和もしくは部分不飽和複素環基。
(82)2−ピリジルオキシ基、3−イソオキサゾリルオキシ基等の複素環オキシ基。
(83)2−ピリジルメチル基、3−ピリジルメチル等のヘテロアリールアルキル基。
(84)2−ピリジルメトキシ基、3−ピリジルメトキシ等のヘテロアリールアルコキシ基。
これら(1)〜(84)に例示された置換基は、さらに(1)〜(84)に例示された置換基を有することもできる。
R4としては、水素原子;メチル基、エチル基等のC1〜C12アルキル基;トリフルオロメチル基、ペンタフルオロエチル基等のC1〜C12ハロアルキル基;シクロプロピル基、シクロペンチル基、シクロヘキシル基等のC3〜C12シクロアルキル基;ビニル基、アリル基等のC2〜C12アルケニル基;3−クロロアリル基等のC2〜C12ハロアルケニル基;プロパルギル基、3−ブチニル基等のC2〜C12アルキニル基;2−クロロエチニル基、2−ブロモエチニル基、3,3,3−トリフルオロ−1−プロピニル基等のC2〜C12ハロアルキニル基;アミノ基;ジメチルアミノ基、ジエチルアミノ基等のジC1〜C6アルキルアミノ基;フェニルアミノ基、4−メチルフェニルアミノ基等の無置換もしくは置換基を有するアリールアミノ基;又は、フェニル基、4−メチルフェニル基、2−クロロフェニル基、2,4−ジフルオロフェニル基等の無置換もしくは置換基を有するアリール基;又は、無置換もしくは置換基を有する複素環基であるのが好ましい。
前記式:−COR3で表される基の具体例としては、−C(=O)NH(CH3)、−C(=O)N(CH3)2、−C(=O)N(CH3)Ph、−C(=O)N(CF3)C2H5、−C(=O)N(CH3)CH2CH=CH2、−C(=O)N(CH3)(cPen)、−CHO、−CO2CH3、−CO2C2H5、−CO2Ph、−CO2CH2CH=CH2、−CO2CF3などが挙げられる。前記cPenはシクロペンチル基を表す(以下にて同じ。)。
前記式:−Si(R5)(R6)(R7)で表される基の具体例としては、−Si(CH3)3、−Si(C2H5)3、−Si(CH3)2(Ph),−Si(Ph)3、−Si(t−C4H9)(CH3)2、−Si(OCH3)3、−Si(OC2H5)3、−Si(OCH3)2CH3などが挙げられる。
置換基を有するアルキル基として、具体的には、クロロメチル基、2−クロロエチル基、トリフルオロメチル基、2,2,2−トリフルオロエチル基、メトキシメチル基、メチルチオメチル基等を例示することができる。
置換基を有するアルケニル基として、具体的には、2−クロロエテニル基、2−フルオロエテニル基、3,3,3−トリフルオロ−1−ペンテニル基、1,2,2−トリフルオロエテニル基、2,3,3−トリフルオロ−2−プロペニル基、2,3,3−トリアイオド−2−プロペニル基、2−メトキシエテニル基等を例示することができる。
置換基を有するアルキニル基として、具体的には、2−クロロエチニル基、2−フルオロエチニル基、3−フルオロ−1−プロピニル基、3,3,3−トリフルオロ−1−プロピニル基、3−フルオロ−2−プロピニル基、3−アイオド−2−プロピニル基等を例示することができる。
前記ハロゲン原子、無置換もしくは置換基を有するアミノ基、及び有機基の具体例としては、前記R0の、ハロゲン原子、無置換もしくは置換基を有するアミノ基、有機基の具体例として列記したものと同様のものが挙げられる。
nは0〜3の整数を表す。nが2以上のとき、複数のYは互いに同一であっても、相異なっていてもよい。
置換基X以外の置換基としては、化学的に許容されるものであれば特に制限されず、前記rと同様のものが挙げられる。
n1は、0〜2のいずれかの整数を表し、n1が2の場合、2つのXは、同一であっても、相異なっていてもよい。
Xは、下記式(II)−1または式(II)−2で表される官能基を表す。
R1、R2は、各々独立して、水素原子、ニトロ基、水酸基、メルカプト基、無置換もしくは置換基を有するアミノ基、又は有機基を表す。
R1、R2の、無置換もしくは置換基を有するアミノ基、有機基の具体例としては、前記R0の、無置換もしくは置換基を有するアミノ基、有機基の具体例として列記したものと同様のものが挙げられる。
R11は、水素原子、水酸基、メルカプト基、無置換もしくは置換基を有するアミノ基、又は有機基を表す。前記R11の、無置換もしくは置換基を有するアミノ基、又は有機基の具体例としては、前記R0の、無置換もしくは置換基を有するアミノ基、有機基の具体例として列記したものと同様のものが挙げられる。これらの中でも、無置換もしくは置換基を有するC1〜C12アルキル基、無置換もしくは置換基を有するC1〜C12アルコキシ基、アルキルアミノ基、無置換もしくは置換基を有するアリール基、無置換もしくは置換基を有する複素環で置換されたC1〜C12アルキル基、無置換もしくは置換基を有するアリールアミノ基が好ましい。
前記R130の、ハロゲン原子、無置換もしくは置換基を有するアミノ基、または有機基の具体例としては、前記R0の、ハロゲン原子、無置換もしくは置換基を有するアミノ基、有機基の具体例として列記したものと同様のものが挙げられる。これらの中でも、R130は、C1〜C12アルキル基、(C1〜C12アルコキシ基、シアノ基、アシル基、無置換もしくは置換基を有するアリール基、または、無置換もしくは置換基を有する複素環基)で置換されたC1〜C12アルキル基、無置換もしくは置換基を有する複素環基、C3〜C12シクロアルキル基、または、無置換もしくは置換基を有するC3〜C12シクロアルケニル基であることが好ましい。
上記式中、A、Y、n、X、および、n1は、前記と同じ意味を表し、飽和窒素原子上は、X、水素原子、または、X以外の置換基が結合しているものとする。
すなわち、先ず、式(V)で表される化合物にハロゲン化剤を作用させて、式(IV)で表される化合物を得る。
ハロゲン化剤の使用量は、式(V)で表される化合物に対して、通常1〜10当量である。
これらの溶媒は一種単独で、或いは二種以上を混合して用いることができる。
得られる式(IV)で表される化合物は、通常、単離することなく次の反応に供することができる。
塩基の使用量は、式(IV)で表される化合物に対して、通常1〜5当量である。
したがって、後述するように、本発明化合物は、有害生物防除剤の有効成分として有用である。
本発明の有害生物防除剤は、前記本発明の第1の態様の含窒素複素環化合物若しくはその塩の少なくとも一種を有効成分として含有する。本発明の有害生物防除剤は、殺虫剤、殺ダニ剤、又は衛生害虫駆除剤であることが好ましい。すなわち、本発明の第2の態様は、前記含窒素複素環化合物若しくはその塩の少なくとも一種を有効成分として含有する殺虫剤に関する。また、本発明の第3の態様は、前記含窒素複素環化合物若しくはその塩の少なくとも一種を有効成分として含有する殺ダニ剤に関する。本発明の第4の態様は、前記含窒素複素環化合物もしくはその塩の少なくとも一種を有効成分として含有する衛生害虫駆除剤に関する。
その代表例として、下記のものが挙げられる。
フルアジナム(fluazinam)などのピリジナミン系化合物;
ベノミル(benomyl)、チオファネートメチル(thiophanate−methyl)、カルベンダジム(carbendazim)、チアベンダゾール(thiabendazole)、フベリアゾール(fuberiazole)、シアゾファミド(cyazofamid)などのイミダゾール系化合物;
シモキサニル(cymoxanil)などのシアノアセトアミド系化合物;
メタラキシル(metalaxyl)、メタラキシル−M(metalaxyl−M)、メフェノキサム(mefenoxam)、オキサジキシル(oxadixyl)、オフレース(ofurace)、ベナラキシル(benalaxyl)、ベナラキシル−M(benalaxyl−M)、フララキシル(furalaxyl)、シプロフラム(cyprofuram)などのフェニルアミド系化合物;
ジクロフルアニド(dichlofluanid)のようなスルフェン酸系化合物;
ジノキャップ(dinocap)などのニトロフェニル系化合物;
水酸化第二銅(cupric hydroxide)、有機銅(oxine copper)などの銅系化合物;
ヒメキサゾール(hymexazol)などのイソキサゾール系化合物;
ホセチルアルミニウム(fosetyl−Al)、トルコホスメチル(tolcofos−methyl)、S−ベンジル O,O−ジイソプロピルホスホロチオエート、O−エチル S,S−ジフェニルホスホロジチオエート、アルミニウムエチルハイドロゲンホスホネートなどの有機リン系化合物;
プロシミドン(procymidone)、イプロジオン(iprodione)、ビンクロゾリン(vinclozolin)などのジカルボキシイミド系化合物;
フルトラニル(flutolanil)、メプロニル(mepronil)、ゾキサミド(zoxamid)、チアジニル(tiadinil)などのベンズアニリド系化合物;カルボキシン(carboxin)、オキシカルボキシン(oxycarboxin)、チフルザミド(thifluzamide)、ペンチオピラド(penthiopyrad)、ボスカリド(boscalid)、フルオピコリド(fluopicolide)、フルオピラム(fluopyram)、ビキサフェン(bixafen)などのアニリド系化合物;
ピリフェノックス(pyrifenox)などのピリジン系化合物;
フェナリモル(fenarimol)、フルトリアフォル(flutriafol)などのカルビノール系化合物;
フェンプロピディン(fenpropidine)などのピペリジン系化合物;
フェンプロピモルフ(fenpropimorph)、トリデモルフ(tridemorph)などのモルフォリン系化合物;
フェンチンヒドロキシド(fentin hydroxide)、フェンチンアセテート(fentin acetate)などの有機スズ系化合物;
ペンシキュロン(pencycuron)などの尿素系化合物;
ジメトモルフ(dimethomorph)、フルモルフ(flumorph)フルメトーバー(flumetover)などのシンナミック酸系化合物;
ジエトフェンカルブ(diethofencarb)などのフェニルカーバメート系化合物;
アゾキシストロビン(azoxystrobin)、クレソキシムメチル(kresoxim−methyl)、メトミノフェン(metominofen)、メトミノストロビン(metominostrobin)、トリフロキシストロビン(trifloxystrobin)、ピコキシストロビン(picoxystrobin)、オリザストロビン(oryzastrobin)、ジモキシストロビン(dimoxystrobin)、ピラクロストロビン(pyraclostrobin)、フルオキサストロビン(fluoxastrobin)などのストロビルリン系化合物;
ファモキサドン(famoxadone)などのオキサゾリジノン系化合物;
エタボキサム(ethaboxam)などのチアゾールカルボキサミド系化合物;
シルチオファム(silthiopham)などのシリルアミド系化合物;
イプロバリカルブ(iprovalicarb)、ベンチアバリカルブ−イソプロピル(benthiavalicarb−isopropyl)などのアミノアシッドアミドカーバメート系化合物;
フェンヘキサミド(fenhexamid)などのハイドロキシアニリド系化合物;
フルスルファミド(flusulfamide)などのベンゼンスルホンアミド系化合物;
シフルフェナミド(cyflufenamid)などのオキシムエーテル系化合物;
フェノキサニル(fenoxanil)などのフェノキシアミド系化合物;
バリダマイシン(validamycin)、カスガマイシン(kasugamycin)、ポリオキシン(polyoxins)などの抗生物質;
イミノクタジン(iminoctadine)などのグアニジン系化合物;
ジコホル(dicofol)、テトラジホン(tetradifon)、エンドスルファン(endosulufan)、ジエノクロル(dienochlor)、ディルドリン(dieldrin)のような有機塩素系化合物;
酸化フェンブタスズ(fenbutatin oxide)、シヘキサチン(cyhexatin)などの有機金属系化合物;
メトプレン(methoprene)、ピリプロキシフェン(pyriproxyfen)、フェノキシカルブ(fenoxycarb)、ジオフェノラン(diofenolan)などの幼若ホルモン様化合物;
フェンピロキシメート(fenpyroximate)、フィプロニル(fipronil)、テブフェンピラド(tebufenpyrad)、エチプロール(ethiprole)、トルフェンピラド(tolfenpyrad)、アセトプロール(acetoprole)、ピラフルプロール(pyrafluprole)、ピリプロール(pyriprole)のようなピラゾール系化合物;
イミダクロプリド(imidacloprid)、ニテンピラム(nitenpyram)、アセタミプリド(acetamiprid)、チアクロプリド(thiacloprid)、チアメトキサム(thiamethoxam)、クロチアニジン(clothianidin)、ジノテフラン(dinotefuran)、ニチアジン(nithiazine)などのネオニコチノイド;
テブフェノジド(tebufenozide)、メトキシフェノジド(methoxyfenozide)、クロマフェノジド(chromafenozide)、ハロフェノジド(halofenozide)などのヒドラジン系化合物;
アザディラクチン(azadirachtin)、ロテノン(rotenone)などのような天然物;
ピペロニルブトキシド(piperonyl butoxide)のような協力剤;
ディート(deet)のような忌避剤などが挙げられる。
N−{5−(3,5−ジクロロフェニル)−5−トリフルオロメチル−4,5−ジヒドロイソオキサゾール−3−イル]インダン−1−イル}−プロピオン酸アミド(化合物番号1−6)の製造
N−(5−ブロモインダン−1−イル)プロピオン酸アミドの製造
5−ブロモインダン−1−イルアミン2.7gをジクロロメタン30mlに溶解させた。この溶液にピリジン2.2gを加え、氷冷下、無水プロピオン酸1.4gを加えた。反応液を室温に戻し、一晩撹拌した後、氷水に注加し、クロロホルムで抽出した。有機層を水、飽和食塩水で洗浄した後、無水硫酸マグネシウムで乾燥した。溶媒を減圧留去し、得られた残渣をシリカゲルカラムクロマトグラフィー(展開溶媒:酢酸エチル/n−ヘキサン=1/1(体積比))で精製し、目的化合物2.4gを得た。収率70%
N−(5−シアノインダン−1−イル)プロピオン酸アミドの製造
N−(5−ブロモインダン−1−イル)プロピオン酸アミド3.64gを1−メチル−2−ピロリドン30mlに溶解させた。この溶液にシアン化第1銅1.8gを加え、2時間加熱還流した。反応液を室温まで冷却し、水に注加した後、1時間撹拌した。得られた反応混合物をセライト濾過し、濾液を酢酸エチルで抽出した。有機層を水、飽和食塩水で洗浄した後、無水硫酸マグネシウムで乾燥した。溶媒を減圧留去し、得られた残渣をシリカゲルカラムクロマトグラフィー(展開溶媒:酢酸エチル/n−ヘキサン=7/3(体積比))で精製し、目的化合物1.46gを得た。収率50%。
N−(5−ホルミルインダン−1−イル)プロピオン酸アミドの製造
N−(5−シアノインダン−1−イル)プロピオン酸アミド1.46gを75%ギ酸水溶液20mlに溶解させた。この溶液にラネーニッケル1.1gを加え、2時間加熱還流した。反応液を室温まで冷却し、セライト濾過した後、溶媒を減圧留去した。得られた残渣を水に注加し、酢酸エチルで抽出、有機層を飽和重曹水、飽和食塩水で洗浄した後、無水硫酸マグネシウムで乾燥した。溶媒を減圧留去し、目的化合物1.18gを得た。収率80%。
N−(5−ホルミルインダン−1−イル)プロピオン酸アミド1.18gをエタノール20ml、水10mlに懸濁させた。この懸濁液に、ヒドロキシアミン塩酸塩0.57g、及び酢酸ナトリム0.67gを加え、室温にて一晩撹拌した。反応液を減圧濃縮後、氷水に注ぎ、酢酸エチルで抽出した。有機層を飽和重曹水、飽和食塩水で洗浄した後、無水硫酸マグネシウムで乾燥した。溶媒を減圧留去し、目的化合物1.25gを得た。収率100%。
N−[5−(ヒドロキシイミノメチル)−インダン−1−イル]プロピオン酸アミド1.25gをN,N−ジメチルホルムアミド20mlに溶解させた。この溶液にN−クロロコハク酸イミド0.8gを加え、50℃にて1時間撹拌した。反応液を0℃に冷却し、3,5−ジクロロ−1−(1−トリフルオロメチルエテニル)ベンゼン1.44g及びトリエチルアミン0.6gを加え、室温で一晩撹拌した。反応液を氷水に注加し、酢酸エチルで抽出、水、飽和食塩水で洗浄した後、無水硫酸マグネシウムで乾燥した。溶媒を減圧留去し、得られた残渣をシリカゲルカラムクロマトグラフィー(展開溶媒:酢酸エチル/n−ヘキサン=1/1(体積比))で精製し、目的化合物1.99gを得た収率77%。
Ph:フェニル
Py:ピリジル
Pr:プロピル
c:シクロ
Hex:ヘキシル
本発明化合物 40部
クレー 48部
ジオクチルスルホサクシネートナトリウム塩 4部
リグニンスルホン酸ナトリウム塩 8部
以上を均一に混合して微細に粉砕し、有効成分40%の水和剤を得る。
本発明化合物 10部
ソルベッソ200 53部
シクロヘキサノン 26部
ドデシルベンゼンスルホン酸カルシウム塩 1部
ポリオキシエチレンアルキルアリルエーテル 10部
以上を混合溶解し、有効成分10%の乳剤を得る。
本発明化合物 10部
クレー 90部
以上を均一に混合して微細に粉砕し、有効成分10%の粉剤を得る。
粒剤
本発明化合物 5部
クレー 73部
ベントナイト 20部
ジオクチルスルホサクシネートナトリウム塩 1部
リン酸カリウム 1部
以上をよく粉砕混合し、水を加えてよく練り合せた後、造粒乾燥して有効成分5%の粒剤を得る。
本発明化合物 10部
ポリオキシエチレンアルキルアリルエーテル 4部
ポリカルボン酸ナトリウム塩 2部
グリセリン 10部
キサンタンガム 0.2部
水 73.8部
以上を混合し、粒度が3ミクロン以下になるまで湿式粉砕し、有効成分10%の懸濁剤を得る。
本発明化合物 40部
クレー 36部
塩化カリウム 10部
アルキルベンゼンスルホン酸ナトリウム塩 1部
リグニンスルホン酸ナトリウム塩 8部
アルキルベンゼンスルホン酸ナトリウム塩の
ホルムアルデヒド縮合物 5部
(試験例1)ワタアブラムシに対する効力
3寸鉢に播種した発芽10日が経過したキュウリにワタアブラムシ成虫を接種した。1日後に成虫を除去し、産下された若虫が寄生するキュウリに、前記製剤実施例2に示された乳剤の処方に従い、化合物濃度が125ppmになるように水で希釈した薬液を散布した。温度25℃、湿度65%の恒温室内に置き、5日後に生死を調べ、殺虫率を求めた。試験は2反復である。その結果、以下の化合物が100%の殺虫率を示した。
(化合物番号は、第1表〜第20表の化合物番号に対応する。以下にて同じ。)
1−5、1−6、1−7、1−8、1−9、1−10、1−11、1−12、1−13、1−14、1−15、1−16、1−17、1−18、1−19、1−20、1−21、1−23、1−25、1−26、1−27、1−28、1−29、1−30、1−31、1−32、1−34、1−35、1−36、1−37、1−38、1−39、1−128、1−135、1−136、1−137、1−138、1−139、1−140、1−141、1−142、1−143、3−6、5−6、5−8、5−12、18−6
対照に用いたピリミカーブの殺虫率は9%であった。
前記の製剤実施例2に示された乳剤の処方に従い、化合物濃度が125ppmになるように水で希釈した。その薬液中にキャベツ葉を30秒間浸漬し風乾後、ろ紙を敷いたシャーレに入れ、ハスモンヨトウ2齢幼虫5頭を接種した。ガラス蓋をして、温度25℃、湿度65%の恒温室内に置き、5日後に生死を調べ、殺虫率を求めた。試験は2反復である。その結果、以下の化合物が100%の殺虫率を示した。
1−5、1−6、1−7、1−8、1−9、1−10、1−11、1−12、1−13、1−14、1−15、1−16、1−17、1−18、1−19、1−20、1−21、1−22、1−23、1−24、1−25、1−26、1−27、1−28、1−29、1−30、1−31、1−32、1−34、1−35、1−36、1−37、1−38、1−39、1−40、1−41、1−128、1−129、1−130、1−134、1−135、1−136、1−137、1−138、1−139、1−140、1−141、1−142、1−143、3−6、5−6、5−8、5−12、5−7、5−10、13−5、13−6、16−6、18−5、18−6、18−7、18−32、18−10、18−16、18−23
対照に用いたクロルジメフォルムの殺虫率は40%であった。
3寸鉢に播種したインゲンの発芽後7〜10日を経過した第1本葉上に、有機リン剤抵抗性のナミハダニ雌成虫を17頭接種したのち、前記薬剤の実施例1に示された水和剤の処方に従い、化合物濃度が125ppmになるように水で希釈した薬液を散布した。温度25℃、湿度65%の恒温室内に置き、3日後に殺成虫率を調査した。試験は2反復である。その結果以下の化合物が100%の殺虫率を示した。
1−5、1−6、1−7、1−8、1−9、1−10、1−11、1−12、1−13、1−14、1−15、1−16、1−17、1−18、1−19、1−20、1−21、1−22、1−23、1−24、1−25、1−26、1−27、1−28、1−29、1−30、1−31、1−32、1−34、1−35、1−36、1−37、1−38、1−39、1−40、1−128、1−129、1−130、1−134、1−135、1−136、1−137、1−138、1−139、1−140、1−141、1−142、1−143、3−6、5−6、5−8、5−12、5−10
対照に用いたクロルジメフォルムの殺虫率は40%であった。
前記の製剤実施例1に示された水和剤の処方に従い、化合物濃度が125ppmになるように水で希釈した。その薬液中にトウモロコシ葉を30秒間浸漬し風乾後、ろ紙を敷いたシャーレに入れ、アワヨトウ2齢幼虫5頭を接種した。ガラス蓋をして、温度25℃、湿度65%の恒温室内に置き、5日後に生死を調べ、殺虫率を求めた。試験は2反復である。その結果、以下の化合物が100%の殺虫率を示した。
1−6、3−6、5−6、5−8、17−88、17−111、14−7、14−8、14−9、14−48
対照に用いたクロルジメフォルムの殺虫率は40%であった。
0.3mlのポリスチレン製試験容器に、孵化1日後のチカイエカ幼虫10頭と観賞魚用飼料(テトラミン、テトラジャパン株式会社)0.5mgを含む蒸留水0.225mlを入れた。
化合物は、DMSO(0.5%tween20を含む)を用いて1%溶液を調整し、さらに蒸留水で0.01%に希釈した。この希釈薬液0.025mlを、チカイエカを入れた試験容器に加え攪拌した(化合物終濃度0.001%)。
25℃に放置し、2日後に殺虫率を調べた。試験は2反復で行った。
本試験において以下の化合物が殺虫率90%以上となり有効であった。
1−6、1−7、1−8、1−10、1−11、1−16、1−20、1−22、1−26、1−27、1−31、1−34、1−35、1−36、1−40、1−41、1−128、3−6、5−6、5−7、5−8、5−10、5−12、8−88、13−5、13−6、16−6、16−7、16−116、17−3、17−91、17−111、20−98
DMSO(0.5%tween20を含む)で希釈調整した1%化合物ストック溶液を水で100倍希釈して所望の0.01%の希釈薬液を得た。90ml容のPET樹脂製カップ底面に5.5cm径の濾紙を敷き、薬液0.7mlを濾紙全体に滴下して30分間放置した。この中にヤマトシロアリの働き蟻10頭を放ち、空気穴を空けた蓋で覆った。
以後、観察室(25℃、60%Rh、14L)に放置し、処理5日後に生死を判定した。試験は2反復で実施した。
本試験において以下の化合物が90%以上の殺虫率を示した。
化合物番号:1−6
1.5mlのエッペンドルフチューブに10%ショ糖水溶液を0.5mlを入れ、DMSO(0.5%tween20を含む)で希釈調整した1%化合物ストック溶液10μlと加温溶解した2%寒天水溶液0.5mlを加えて良く攪拌した。これを速やかに遠沈し、化合物を0.01%含有する毒餌を得た。
90mlのPET樹脂製カップに5.5cm径の濾紙と毒餌を入れ、この中にチャバネゴキブリ1齢幼虫20頭を放ち空気穴を空けた蓋で覆った。
以後観察室(25℃、60%Rh、14L)に放置し、5日後に生死の判定を行った。試験は2反復で実施した。
本試験において以下の化合物が90%以上の殺虫率を示した。
化合物番号:1−6
Claims (10)
- 下記式(I):
R0は、ニトロ基、水酸基、メルカプト基、ハロゲン原子、無置換もしくは置換基を有するアミノ基、又は有機基を表し;
Zは、無置換もしくは置換基を有するアリール基、無置換もしくは置換基を有する複素環基、無置換もしくは置換基を有するアルキル基、無置換もしくは置換基を有するアルケニル基、または無置換もしくは置換基を有するアルキニル基を表し;
Qは、下記式(I’):
Yは、ニトロ基、水酸基、メルカプト基、ハロゲン原子、無置換もしくは置換基を有するアミノ基、又は有機基を表し;
nは0〜3の整数を表し、nが2以上のとき、複数のYは互いに同一であっても、相異なっていてもよく、2つのYが隣接する場合には、2つのYが一緒になって結合して、4〜6員環を形成してもよく;
Dは、置換基X以外の置換基を有さない、または、有する、5〜8員環の炭化水素環基または複素環基を表し;
Xは、下記式(II)−1または式(II)−2:
R1とR2は、各々独立して、水素原子、ニトロ基、水酸基、メルカプト基、無置換もしくは置換基を有するアミノ基、又は有機基を表し、R1とR2は、一緒になって結合して3〜8員環を形成していてもよく、R1とR2は、一緒になって二重結合を形成し、下記式:
式(II)−2中、Wは酸素原子または硫黄原子を表し;
R11は、水素原子、水酸基、メルカプト基、無置換もしくは置換基を有するアミノ基、又は有機基を表す。)で表される官能基を表し;
n1は、0〜2のいずれかの整数を表し、n1が2の場合、2つのXは、同一であっても、相異なっていてもよく;
Aは、炭素原子または窒素原子を表し、炭素原子であって、炭素原子上にYで表される置換基を有さない場合には、水素原子が結合、またはR1またはR2と結合して環を形成する。)
で示される基を表す。)
で表される含窒素複素環化合物又はその塩。 - 前記式(I’)中、Xは、式(II)−1を表す、請求項1に記載の含窒素複素環化合物又はその塩。
- 前記式(I)中、Zは、無置換もしくは置換基を有するフェニル基、又は、無置換もしくは置換基を有し、窒素原子、酸素原子および硫黄原子からなる群から選択されるヘテロ原子を少なくとも一つ含有する、5又は6員複素環基を表す、請求項1〜4のいずれか一項に記載の含窒素複素環化合物またはその塩。
- 前記式(I)中、R0は、C1〜C12ハロアルキル基を表す、請求項1〜5のいずれか一項に記載の含窒素複素環化合物またはその塩。
- 前記式(I’)中、Yはハロゲン原子、C1〜C6アルキル基、C1〜C6アルコキシ基、C1〜C6ハロアルキル基、又は、C1〜C6ハロアルコキシ基を表す、あるいは、nが0を表す、請求項1〜6のいずれか一項に記載の含窒素複素環化合物またはその塩。
- 請求項1〜7のいずれか一項に記載の含窒素複素環化合物若しくはその塩の少なくとも一種を有効成分として含有する殺虫剤。
- 請求項1〜7のいずれか一項に記載の含窒素複素環化合物若しくはその塩の少なくとも一種を有効成分として含有する殺ダニ剤。
- 請求項1〜7のいずれか一項に記載の含窒素複素環化合物もしくはその塩の少なくとも一種を有効成分として含有する衛生害虫駆除剤。
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US20110124858A1 (en) | 2011-05-26 |
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JP5128600B2 (ja) | 2013-01-23 |
CA2700598C (en) | 2012-11-20 |
EP2186804A1 (en) | 2010-05-19 |
CA2700598A1 (en) | 2009-02-19 |
EP2186804B1 (en) | 2015-06-17 |
CN101778833A (zh) | 2010-07-14 |
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