JP6717961B2 - 1h‐ピロロピリジン化合物、若しくはそのn‐オキサイド、又はその塩類及び該化合物を含有する農園芸用殺虫剤並びにその使用方法 - Google Patents
1h‐ピロロピリジン化合物、若しくはそのn‐オキサイド、又はその塩類及び該化合物を含有する農園芸用殺虫剤並びにその使用方法 Download PDFInfo
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- JP6717961B2 JP6717961B2 JP2018545065A JP2018545065A JP6717961B2 JP 6717961 B2 JP6717961 B2 JP 6717961B2 JP 2018545065 A JP2018545065 A JP 2018545065A JP 2018545065 A JP2018545065 A JP 2018545065A JP 6717961 B2 JP6717961 B2 JP 6717961B2
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- alkoxy
- alkyl
- alkylthio
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Classifications
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/14—Ectoparasiticides, e.g. scabicides
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- 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
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
-
- 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
- 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
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
- A01N47/16—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof the nitrogen atom being part of a heterocyclic ring
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
- A61K31/4439—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. omeprazole
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
- A61K31/444—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a six-membered ring with nitrogen as a ring heteroatom, e.g. amrinone
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Dentistry (AREA)
- Engineering & Computer Science (AREA)
- Plant Pathology (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Veterinary Medicine (AREA)
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Description
[1] 一般式(1)
(a2) シアノ基;
(a3)(C1-C6)アルキル基;
(a4)(C3-C6)シクロアルキル基;
(a5)(C2-C6)アルケニル基;
(a6)(C2-C6)アルキニル基;
(a7)(C1-C6)アルキルカルボニル基;又は
(a8)(C1-C6)アルコキシカルボニル基;を示す。
R2は、 (b1) 水素原子;
(b2)(C1-C6)アルキル基;
(b3)(C1-C6)アルキルカルボニル基;
(b4)(C1-C6)アルコキシカルボニル基;
(b5)ハロ(C1-C6)アルコキシ基;
(b6)(C1-C6)アルコキシ(C1-C6)アルキル基;
(b7)(C1-C6)アルキルチオ(C1-C6)アルキル基;
(b8)(C2-C6)アルケニル基;
(b9)(C2-C6)アルキニル基;又は
(b10) シクロ(C3-C6)アルキル(C1-C6)アルキル基;を示す。
R3は、
(c1) 水素原子;
(c2) ハロゲン原子;
(c3) シアノ基;
(c4) ニトロ基;
(c5)(C1-C6)アルキル基;
(c6)(C3-C6)シクロアルキル基;
(c7) シアノ(C3-C6)シクロアルキル基;
(c8)(C1-C6)アルコキシ基;
(c9) ハロ(C1-C6)アルキル基;
(c10) ハロ(C1-C6)アルコキシ基;
(c11)(C1-C6)アルキルチオ基;
(c12) ハロ(C1-C6)アルキルチオ基;
(c13)(C1-C6)アルキルスルフィニル基;
(c14) ハロ(C1-C6)アルキルスルフィニル基;
(c15)(C1-C6)アルキルスルホニル基;又は
(c16) ハロ(C1-C6)アルキルスルホニル基;を示す。
R4又はR5は、同一又は異なってもよく、
(d1) 水素原子;
(d2) ハロゲン原子;
(d3) シアノ基;
(d4) ニトロ基;
(d4) ホルミル基;
(d5)(C1-C6)アルキル基;
(d6)(C1-C6)アルコキシ基;
(d7)(C3-C6)シクロアルキル基;
(d8) R6(R7)N基(式中、R6及びR7は、同一又は異なっても良く、水素原子、(C1-C6)アルキル基、(C3-C6)シクロアルキル基、(C3-C6)シクロアルキル(C1-C6)アルキル基、ハロ(C1-C6)アルキル基、(C1-C6)アルキルカルボニル基、(C1-C6)アルコキシカルボニル基、フェニル基、又はフェニル(C1-C6)アルキル基を示す。);
(d9) C(R6)=NOR7基(式中、R6及びR7は前記に同じ。);
(d10) ハロ(C1-C6)アルキル基;
(d11) ハロ(C1-C6)アルコキシ基;
(d12)(C1-C6)アルキルチオ基;
(d13) ハロ(C1-C6)アルキルチオ基;
(d14)(C1-C6)アルキルスルフィニル基;
(d15) ハロ(C1-C6)アルキルスルフィニル基;
(d16)(C1-C6)アルキルスルホニル基;
(d17) ハロ(C1-C6)アルキルスルホニル基;
(d18)(C1-C6)アルキルカルボニル基;
(d19) アリール基;
(d20) 同一又は異なっても良く、(a)ハロゲン原子、(b)シアノ基、(c)ニトロ基、(d)ホルミル基、(e)(C1−C6)アルキル基、(f)ハロ(C1−C6)アルキル基、(g)(C1−C6)アルコキシ基、(h)ハロ(C1−C6)アルコキシ基、(i)(C3−C6)シクロアルキル(C1−C6)アルコキシ基、(j)(C1−C6)アルキルチオ基、(k)ハロ(C1−C6)アルキルチオ基、(l)(C1−C6)アルキルスルフィニル基、(m)ハロ(C1−C6)アルキルスルフィニル基、(n)(C1−C6)アルキルスルホニル基、(o)ハロ(C1−C6)アルキルスルホニル基、(p)(C1−C6)アルキルカルボニル基、(q)カルボキシル基、及び(r)(C1−C6)アルコキシカルボニル基から選択される1〜5の置換基を環上に有するアリール基;
(d21) 複素環基;
(d22) 同一又は異なっても良く、(a)ハロゲン原子、(b)シアノ基、(c)ニトロ基、(d)ホルミル基、(e)(C1−C6)アルキル基、(f)ハロ(C1−C6)アルキル基、(g)(C1−C6)アルコキシ基、(h)ハロ(C1−C6)アルコキシ基、(i)(C3−C6)シクロアルキル(C1−C6)アルコキシ基、(j)(C1−C6)アルキルチオ基、(k)ハロ(C1−C6)アルキルチオ基、(l)(C1−C6)アルキルスルフィニル基、(m)ハロ(C1−C6)アルキルスルフィニル基、(n)(C1−C6)アルキルスルホニル基、(o)ハロ(C1−C6)アルキルスルホニル基、(p)(C1−C6)アルキルカルボニル基、(q)カルボキシル基、及び(r)(C1−C6)アルコキシカルボニル基から選択される1〜2の置換基を環上に有する複素環基;
(d23) アリールオキシ基;
(d24) 同一又は異なっても良く、(a)ハロゲン原子、(b)シアノ基、(c)ニトロ基、(d)ホルミル基、(e)(C1−C6)アルキル基、(f)ハロ(C1−C6)アルキル基、(g)(C1−C6)アルコキシ基、(h)ハロ(C1−C6)アルコキシ基、(i)(C3−C6)シクロアルキル(C1−C6)アルコキシ基、(j)(C1−C6)アルキルチオ基、(k)ハロ(C1−C6)アルキルチオ基、(l)(C1−C6)アルキルスルフィニル基、(m)ハロ(C1−C6)アルキルスルフィニル基、(n)(C1−C6)アルキルスルホニル基、(o)ハロ(C1−C6)アルキルスルホニル基、(p)(C1−C6)アルキルカルボニル基、(q)カルボキシル基、及び(r)(C1−C6)アルコキシカルボニル基から選択される1〜5の置換基を環上に有するアリールオキシ基;
(d25) アリール(C1-C6)アルコキシ基;又は
(d26) 同一又は異なっても良く、(a)ハロゲン原子、(b)シアノ基、(c)ニトロ基、(d)ホルミル基、(e)(C1−C6)アルキル基、(f)ハロ(C1−C6)アルキル基、(g)(C1−C6)アルコキシ基、(h)ハロ(C1−C6)アルコキシ基、(i)(C3−C6)シクロアルキル(C1−C6)アルコキシ基、(j)(C1−C6)アルキルチオ基、(k)ハロ(C1−C6)アルキルチオ基、(l)(C1−C6)アルキルスルフィニル基、(m)ハロ(C1−C6)アルキルスルフィニル基、(n)(C1−C6)アルキルスルホニル基、(o)ハロ(C1−C6)アルキルスルホニル基、(p)(C1−C6)アルキルカルボニル基、(q)カルボキシル基、及び(r)(C1−C6)アルコキシカルボニル基から選択される1〜5の置換基を環上に有するアリール(C1-C6)アルコキシ基;を示す。
A及びA1は、同一又は異なってもよく、窒素原子、N‐オキサイド又はC-R8基を示す(ここでR8は、 (e1) 水素原子; (e2) ハロゲン原子; (e3) シアノ基; (e4) ニトロ基; (e5) ホルミル基; (e6)(C1-C6)アルキル基; 又は (e7)(C1-C6)アルコキシ基;を表す。)。mは0、1または2を示す。}で表される縮合複素環化合物、若しくはそのN-オキサイド、又はその塩類、
[2] R1が、 (a1) ハロゲン原子;
(a2) シアノ基;
(a3)(C1-C6)アルキル基;
(a5)(C2-C6)アルケニル基; 又は
(a8)(C1-C6)アルコキシカルボニル基;を示し、
R2が、 (b1) 水素原子;
(b2)(C1-C6)アルキル基;
(b3)(C1-C6)アルキルカルボニル基;
(b4)(C1-C6)アルコキシカルボニル基;
(b5)ハロ(C1-C6)アルコキル基;
(b6)(C1-C6)アルコキシ(C1-C6)アルキル基;
(b7)(C1-C6)アルキルチオ(C1-C6)アルキル基;
(b8)(C2-C6)アルケニル基;
(b9)(C2-C6)アルキニル基;又は
(b10) シクロ(C3-C6)アルキル(C1-C6)アルキル基;を示し、
R3が、
(c9) ハロ(C1-C6)アルキル基; を示し、
R4又はR5が、同一又は異なってもよく、
(d2) ハロゲン原子;
(d4) ホルミル基;
(d6)(C1-C6)アルコキシ基;
(d7)(C3-C6)シクロアルキル基;
(d8) R6(R7)N基(式中、R6及びR7は、同一又は異なっても良く、水素原子、(C1-C6)アルキル基、(C3-C6)シクロアルキル基、(C3-C6)シクロアルキル(C1-C6)アルキル基、ハロ(C1-C6)アルキル基、(C1-C6)アルキルカルボニル基、(C1-C6)アルコキシカルボニル基、フェニル基、又はフェニル(C1-C6)アルキル基を示す。)
(d9) C(R6)=NOR7基(式中、R6及びR7は前記に同じ。);
(d10) ハロ(C1-C6)アルキル基;
(d11) ハロ(C1-C6)アルコキシ基;
(d12)(C1-C6)アルキルチオ基;
(d13) ハロ(C1-C6)アルキルチオ基;
(d16)(C1-C6)アルキルスルホニル基;
(d18)(C1-C6)アルキルカルボニル基;
(d20) 同一又は異なっても良く、(a)ハロゲン原子、(b)シアノ基、(c)ニトロ基、(d)ホルミル基、(e)(C1−C6)アルキル基、(f)ハロ(C1−C6)アルキル基、(g)(C1−C6)アルコキシ基、(h)ハロ(C1−C6)アルコキシ基、(i)(C3−C6)シクロアルキル(C1−C6)アルコキシ基、(j)(C1−C6)アルキルチオ基、(k)ハロ(C1−C6)アルキルチオ基、(l)(C1−C6)アルキルスルフィニル基、(m)ハロ(C1−C6)アルキルスルフィニル基、(n)(C1−C6)アルキルスルホニル基、(o)ハロ(C1−C6)アルキルスルホニル基、(p)(C1−C6)アルキルカルボニル基、(q)カルボキシル基、及び(r)(C1−C6)アルコキシカルボニル基から選択される1〜5の置換基を環上に有するアリール基;
(d21) 複素環基;
(d22) 同一又は異なっても良く、(a)ハロゲン原子、(b)シアノ基、(c)ニトロ基、(d)ホルミル基、(e)(C1−C6)アルキル基、(f)ハロ(C1−C6)アルキル基、(g)(C1−C6)アルコキシ基、(h)ハロ(C1−C6)アルコキシ基、(i)(C3−C6)シクロアルキル(C1−C6)アルコキシ基、(j)(C1−C6)アルキルチオ基、(k)ハロ(C1−C6)アルキルチオ基、(l)(C1−C6)アルキルスルフィニル基、(m)ハロ(C1−C6)アルキルスルフィニル基、(n)(C1−C6)アルキルスルホニル基、(o)ハロ(C1−C6)アルキルスルホニル基、(p)(C1−C6)アルキルカルボニル基、(q)カルボキシル基、及び(r)(C1−C6)アルコキシカルボニル基から選択される1〜2の置換基を環上に有する複素環基;
(d24) 同一又は異なっても良く、(a)ハロゲン原子、(b)シアノ基、(c)ニトロ基、(d)ホルミル基、(e)(C1−C6)アルキル基、(f)ハロ(C1−C6)アルキル基、(g)(C1−C6)アルコキシ基、(h)ハロ(C1−C6)アルコキシ基、(i)(C3−C6)シクロアルキル(C1−C6)アルコキシ基、(j)(C1−C6)アルキルチオ基、(k)ハロ(C1−C6)アルキルチオ基、(l)(C1−C6)アルキルスルフィニル基、(m)ハロ(C1−C6)アルキルスルフィニル基、(n)(C1−C6)アルキルスルホニル基、(o)ハロ(C1−C6)アルキルスルホニル基、(p)(C1−C6)アルキルカルボニル基、(q)カルボキシル基、及び(r)(C1−C6)アルコキシカルボニル基から選択される1〜5の置換基を環上に有するアリールオキシ基;
(d25) アリール(C1-C6)アルコキシ基;又は
(d26) 同一又は異なっても良く、(a)ハロゲン原子、(b)シアノ基、(c)ニトロ基、(d)ホルミル基、(e)(C1−C6)アルキル基、(f)ハロ(C1−C6)アルキル基、(g)(C1−C6)アルコキシ基、(h)ハロ(C1−C6)アルコキシ基、(i)(C3−C6)シクロアルキル(C1−C6)アルコキシ基、(j)(C1−C6)アルキルチオ基、(k)ハロ(C1−C6)アルキルチオ基、(l)(C1−C6)アルキルスルフィニル基、(m)ハロ(C1−C6)アルキルスルフィニル基、(n)(C1−C6)アルキルスルホニル基、(o)ハロ(C1−C6)アルキルスルホニル基、(p)(C1−C6)アルキルカルボニル基、(q)カルボキシル基、及び(r)(C1−C6)アルコキシカルボニル基から選択される1〜5の置換基を環上に有するアリール(C1-C6)アルコキシ基; を示す、請求項1に記載の縮合複素環化合物、若しくはそのN-オキサイド、又はその塩類、
[3] R1が、 (a1) ハロゲン原子;
(a2) シアノ基;
(a3)(C1-C6)アルキル基;
(a5)(C2-C6)アルケニル基; 又は
(a8)(C1-C6)アルコキシカルボニル基;を示し、
R2が、 (b1) 水素原子; (b2)(C1-C6)アルキル基;
(b3)(C1-C6)アルキルカルボニル基;
(b4)(C1-C6)アルコキシカルボニル基;
(b5)ハロ(C1-C6)アルコキル基;
(b6)(C1-C6)アルコキシ(C1-C6)アルキル基;
(b7)(C1-C6)アルキルチオ(C1-C6)アルキル基;
(b8)(C2-C6)アルケニル基;
(b9)(C2-C6)アルキニル基;又は
(b10) シクロ(C3-C6)アルキル(C1-C6)アルキル基;を示し、
R3が、
(c9) ハロ(C1-C6)アルキル基;を示し、
R4又はR5が、同一又は異なってもよく、
(d2) ハロゲン原子;
(d4) ホルミル基;
(d6)(C1-C6)アルコキシ基;
(d7)(C3-C6)シクロアルキル基;
(d9) C(R6)=NOR7基(式中、R6及びR7は、同一又は異なっても良く、水素原子、(C1-C6)アルキル基、(C3-C6)シクロアルキル基、(C3-C6)シクロアルキル(C1-C6)アルキル基、ハロ(C1-C6)アルキル基、(C1-C6)アルキルカルボニル基、(C1-C6)アルコキシカルボニル基、フェニル基、又はフェニル(C1-C6)アルキル基を示す。);
(d10) ハロ(C1-C6)アルキル基;
(d11) ハロ(C1-C6)アルコキシ基;
(d20) 同一又は異なっても良く、(a)ハロゲン原子、(b)シアノ基、(c)ニトロ基、(d)ホルミル基、(e)(C1−C6)アルキル基、(f)ハロ(C1−C6)アルキル基、(g)(C1−C6)アルコキシ基、(h)ハロ(C1−C6)アルコキシ基、(i)(C3−C6)シクロアルキル(C1−C6)アルコキシ基、(j)(C1−C6)アルキルチオ基、(k)ハロ(C1−C6)アルキルチオ基、(l)(C1−C6)アルキルスルフィニル基、(m)ハロ(C1−C6)アルキルスルフィニル基、(n)(C1−C6)アルキルスルホニル基、(o)ハロ(C1−C6)アルキルスルホニル基、(p)(C1−C6)アルキルカルボニル基、(q)カルボキシル基、及び(r)(C1−C6)アルコキシカルボニル基から選択される1〜5の置換基を環上に有するアリール基;
(d21) 複素環基;
(d22) 同一又は異なっても良く、(a)ハロゲン原子、(b)シアノ基、(c)ニトロ基、(d)ホルミル基、(e)(C1−C6)アルキル基、(f)ハロ(C1−C6)アルキル基、(g)(C1−C6)アルコキシ基、(h)ハロ(C1−C6)アルコキシ基、(i)(C3−C6)シクロアルキル(C1−C6)アルコキシ基、(j)(C1−C6)アルキルチオ基、(k)ハロ(C1−C6)アルキルチオ基、(l)(C1−C6)アルキルスルフィニル基、(m)ハロ(C1−C6)アルキルスルフィニル基、(n)(C1−C6)アルキルスルホニル基、(o)ハロ(C1−C6)アルキルスルホニル基、(p)(C1−C6)アルキルカルボニル基、(q)カルボキシル基、及び(r)(C1−C6)アルコキシカルボニル基から選択される1〜2の置換基を環上に有する複素環基;
(d24) 同一又は異なっても良く、(a)ハロゲン原子、(b)シアノ基、(c)ニトロ基、(d)ホルミル基、(e)(C1−C6)アルキル基、(f)ハロ(C1−C6)アルキル基、(g)(C1−C6)アルコキシ基、(h)ハロ(C1−C6)アルコキシ基、(i)(C3−C6)シクロアルキル(C1−C6)アルコキシ基、(j)(C1−C6)アルキルチオ基、(k)ハロ(C1−C6)アルキルチオ基、(l)(C1−C6)アルキルスルフィニル基、(m)ハロ(C1−C6)アルキルスルフィニル基、(n)(C1−C6)アルキルスルホニル基、(o)ハロ(C1−C6)アルキルスルホニル基、(p)(C1−C6)アルキルカルボニル基、(q)カルボキシル基、及び(r)(C1−C6)アルコキシカルボニル基から選択される1〜5の置換基を環上に有するアリールオキシ基;
(d25) アリール(C1-C6)アルコキシ基;又は
(d26) 同一又は異なっても良く、(a)ハロゲン原子、(b)シアノ基、(c)ニトロ基、(d)ホルミル基、(e)(C1−C6)アルキル基、(f)ハロ(C1−C6)アルキル基、(g)(C1−C6)アルコキシ基、(h)ハロ(C1−C6)アルコキシ基、(i)(C3−C6)シクロアルキル(C1−C6)アルコキシ基、(j)(C1−C6)アルキルチオ基、(k)ハロ(C1−C6)アルキルチオ基、(l)(C1−C6)アルキルスルフィニル基、(m)ハロ(C1−C6)アルキルスルフィニル基、(n)(C1−C6)アルキルスルホニル基、(o)ハロ(C1−C6)アルキルスルホニル基、(p)(C1−C6)アルキルカルボニル基、(q)カルボキシル基、及び(r)(C1−C6)アルコキシカルボニル基から選択される1〜5の置換基を環上に有するアリール(C1-C6)アルコキシ基;を示す、[1]に記載の縮合複素環化合物、若しくはそのN-オキサイド、又はその塩類、
[4] [1]乃至[3]の何れか1項に記載の縮合複素環化合物、若しくはそのN-オキサイド、又はその塩類の農園芸用殺虫剤としての使用、
[5] [4]に記載の農園芸用殺虫剤の有効成分で植物又は土壌を処理することを特徴とする農園芸用殺虫剤の使用方法、
[6] [4]に記載の農園芸用殺虫剤の有効量で植物又は土壌を処理することを特徴とする農園芸用害虫の防除方法、
[7] [1]乃至[3]の何れか1項に記載の縮合複素環化合物、若しくはそのN-オキサイド、又はその塩類を有効成分として含有することをと特徴とする動物用の外部寄生虫防除剤、並びに
[8] [7]に記載の動物用の外部寄生虫防除剤の有効量で動物の外部寄生虫を処理することを特徴とする動物用外部寄生虫の防除方法、に関する。
「(C3‐C6)シクロアルコキシ基」とは、例えば、シクロプロポキシ基、シクロブトキシ基、シクロペンチルオキシ基、シクロヘキシルオキシ基等の炭素原子数3〜6個の環状のアルコキシ基を示し、「(C3‐C6)シクロアルキルチオ基」とは、例えば、シクロプロピルチオ基、シクロブチルチオ基、シクロペンチルチオ基、シクロヘキシルチオ基等の炭素原子数3〜6個の環状のアルキルチオ基を示し、「(C3‐C6)シクロアルキルスルフィニル基」とは、例えば、シクロプロピルスルフィニル基、シクロブチルスルフィニル基、シクロペンチルスルフィニル基、シクロヘキシルスルフィニル基等の炭素原子数3〜6個の環状のアルキルスルフィニル基を示し、「(C3‐C6)シクロアルキルスルホニル基」とは、例えばシクロプロピルスルホニル基、シクロブチルスルホニル基、シクロペンチルスルホニル基、シクロヘキシルスルホニル基等の炭素原子数3〜6個の環状のアルキルスルホニル基を示す。
一般式(2‐3)で表される化合物は、後述の中間体製法1、又は国際公開第2014/157600号パンフレットに記載の製造方法に従って製造した一般式(2‐4)で表される化合物を、Greene’s Protective Groups in Organic Synthesis(John Wiley & Sons Inc.)に記載された方法により、製造することができる。
一般式(2‐2)で表される化合物は、一般式(2‐3)で表される化合物を、不活性溶媒中、酸化剤で反応することにより製造することができる。
一般式(2‐1)で表される化合物は、一般式(2‐2)で表される化合物を、Greene’s Protective Groups in Organic Synthesis(John Wiley & Sons Inc.)に記載された方法により、製造することができる。
一般式(1‐1)で表される化合物は、一般式(2‐1)で表される化合物を、活性溶媒中、ハロゲン化剤で反応することにより製造することができる。
一般式(1)で表される1H‐ピロロ縮合複素環化合物は、一般式(1‐1)で表される化合物を、不活性溶媒中、塩基の存在下、R2‐Lと反応することにより製造することができる。
芳香族環カルボン酸エステルと酢酸エステルとのクライゼン縮合反応(Org. React. 1942, 1, 266)、及びエステル変換により製造した一般式(3‐3)で表されるβ‐ケトエステル化合物と、一般式(4)で表されるハロゲン化されたニトロ化合物とを不活性溶媒中、塩基の存在下に反応させることにより、一般式(3‐2)で表される化合物を得ることができる。
反応温度は通常、室温から使用する溶媒の沸点の範囲内である。反応時間は、通常、数分間から数十時間である。反応は好ましくは不活性ガス雰囲気下で行う。反応終了後、目的物を含む反応系から常法により単離すれば良く、必要に応じて再結晶、カラムクロマトグラフィー等で精製することにより目的物を製造することができる。
一般式(3‐2)で表される化合物を、溶媒の存在又は非存在下、酸で処理すれば一般式(3‐1)で表される化合物を製造することができる。
反応終了後、目的物を含む反応系から目的物を常法により単離すれば良く、必要に応じて再結晶、カラムクロマトグラフィー等で精製することにより目的物を製造することができる。
本反応は、一般式(3‐1)で表されるニトロ化合物を、還元反応及び脱水反応により一般式(2‐4)で表される1H‐ピロロ縮合複素環化合物を製造することができる。
物性は融点(℃)、屈折率(℃)又はNMRを示し、1H‐NMRデータは第20表〜第22表に示す。
鱗翅目(チョウ目)害虫として例えば、アオイラガ(Parasa consocia)、アカキリバ(Anomis mesogona)、アゲハ(Papilio xuthus)、アズキサヤムシガ(Matsumuraeses azukivora)、アズキノメイガ(Ostrinia scapulalis)、アフリカヨトウ(Spodoptera exempta)、アメリカシロヒトリ(Hyphantria cunea)、アワノメイガ(Ostrinia furnacalis)、アワヨトウ(Pseudaletia separata)、イガ(Tinea translucens)、イグサシンムシガ(Bactra furfuryla)、イチモンジセセリ(Parnara guttata)、イネタテハマキ(Marasmia exigua)、イネツトムシ(Parnara guttata)、イネヨトウ(Sesamia inferens)、イモキバガ(Brachmia triannulella)、イラガ(Monema flavescens)、イラクサギンウワバ(Trichoplusia ni)、ウコンノメイガ(Pleuroptya ruralis)、ウメエダシャク(Cystidia couaggaria)、ウラナミシジミ(Lampides boeticus)、オオスカシバ(Cephonodes hylas)、オオタバコガ(Helicoverpa armigera)、オオトビモンシャチホコ(Phalerodonta manleyi)、オオミノガ(Eumeta japonica)、オオモンシロチョウ(Pieris brassicae)、オビカレハ(Malacosoma neustria testacea)、カキノヘタムシガ(Stathmopoda masinissa)、カキホソガ(Cuphodes diospyrosella)、カクモンハマキ(Archips xylosteanus)、カブラヤガ(Agrotis segetum)、カンショシンクイハマキ(Tetramoera schistaceana)、キアゲハ(Papilio machaon hippocrates)、キマダラコウモリ(Endoclyta sinensis)、ギンモンハモグリガ(Lyonetia prunifoliella)、キンモンホソガ(Phyllonorycter ringoneella)、クリミガ(Cydia kurokoi)、クリミドリシンクイガ(Eucoenogenes aestuosa)、グレープベリーモス(Lobesia botrana)、クロシタアオイラガ(Latoia sinica)、クロフタモンマダラメイガ(Euzophera batangensis)、クワイホソハマキ(Phalonidia mesotypa)、クワゴマダラヒトリ(Spilosoma imparilis)、クワノメイガ(Glyphodes pyloalis)、クワヒメハマキ(Olethreutes mori)、コイガ(Tineola bisselliella)、コウモリガ(Endoclyta excrescens)、コクガ(Nemapogon granellus)、コスカシバ(Synanthedon hector)、コドリンガ(Cydia pomonella)、コナガ(Plutella xylostella)、コブノメイガ(Cnaphalocrocis medinalis)、
これら毒素の例及びこれら毒素を合成する事ができる組換え植物は、EP−A−0 374 753、WO 93/07278、WO 95/34656、EP−A−0 427 529、EP−A−451 878、WO 03/052073等に記載されている。
更に、本発明の農園芸用殺虫剤は、そのまま、又は水等で適宜希釈し、若しくは懸濁させた形で害虫防除に有効な量を当該害虫の発生が予測される場所に使用すればよく、例えば貯穀害虫、家屋害虫、衛生害虫、森林害虫等に散布する他に、家屋建材への塗布、くん煙、ベイト等として使用することもできる。
当該種子処理を行う「種子」とは、植物の繁殖に用いられる栽培初期の植物体を意味し、例えば、種子の他、球根、塊茎、種芋、株芽、むかご、鱗茎、あるいは挿し木栽培用の栄養繁殖用の植物体を挙げることができる。
本発明の使用方法を実施する場合の植物の「土壌」又は「栽培担体」とは、作物を栽培するための支持体、特に根を生えさせる支持体を示すものであり、材質は特に制限されないが、植物が生育しうる材質であれば良く、いわゆる土壌、育苗マット、水等であっても良く、具体的な素材としては例えば、砂、軽石、バーミキュライト、珪藻土、寒天、ゲル状物質、高分子物質、ロックウール、グラスウール、木材チップ、バーク等であっても良い。
土壌への施用方法としては、例えば、液体製剤を水に希釈又は希釈せずして植物体の株元または育苗用苗床等に施用する方法、粒剤を植物体の株元又は育苗のための苗床等に散布する方法、播種前または移植前に粉剤、水和剤、顆粒水和剤、粒剤等を散布し土壌全体と混和する方法、播種前または植物体を植える前に植え穴、作条等に粉剤、水和剤、顆粒水和剤、粒剤等を散布する方法等が挙げられる。
水田への施用方法としては、ジャンボ剤、パック剤、粒剤、顆粒水和剤等の固形製剤、フロアブル、乳剤等の液体状製剤を、通常は、湛水状態の水田に散布する。その他、田植え時には、適当な製剤をそのまま、あるいは、肥料に混和して土壌に散布、注入することもできる。また、水口や灌漑装置等の水田への水の流入元に乳剤、フロアブル等の薬液を利用することにより、水の供給に伴い省力的に施用することもできる。
移植を行う栽培植物の播種、育苗期の処理としては、種子への直接処理の他、育苗用苗床への、液状とした薬剤の潅注処理又は粒剤の散布処理が好ましい。また、定植時に粒剤を植え穴に処理をしたり、移植場所近辺の栽培担体に混和することも好ましい処理である。
本発明の農園芸用殺虫剤は、農薬製剤上の常法に従い使用上都合の良い形状に製剤して使用するのが一般的である。
即ち、本発明の一般式(1)で表される縮合複素環化合物、若しくはそのN−オキサイド、又はその塩類はこれらを適当な不活性担体に、又は必要に応じて補助剤と一緒に適当な割合に配合して溶解、分離、懸濁、混合、含浸、吸着若しくは付着させて適宜の剤型、例えば懸濁剤、乳剤、液剤、水和剤、顆粒水和剤、粒剤、粉剤、錠剤、パック剤等に製剤して使用すれば良い。
更に必要に応じて機能性展着剤、ピペロニルブトキサイド等の代謝分解阻害剤等の活性増強剤、プロピレングリコール等の凍結防止剤、BHT等の酸化防止剤、紫外線吸収剤等その他の補助剤も使用することができる。
3,5-xylyl methylcarbamate(XMC)、Bacillus thuringienses aizawai、Bacillus thuringienses israelensis、Bacillus thuringienses japonensis、Bacillus thuringienses kurstaki、Bacillus thuringienses tenebrionis、Bacillus thuringiensesが生成する結晶タンパク毒素、BPMC、Btトキシン系殺虫性化合物、CPCBS(chlorfenson)、DCIP(dichlorodiisopropyl ether)、D-D(1, 3-Dichloropropene)、DDT、NAC、O-4-dimethylsulfamoylphenyl O,O-diethyl phosphorothioate(DSP)、O-ethyl O-4-nitrophenyl phenylphosphonothioate(EPN)、tripropylisocyanurate(TPIC)、アクリナトリン(acrinathrin)、アザディラクチン(azadirachtin)、アジンホス・メチル(azinphos-methyl)、アセキノシル(acequinocyl)、アセタミプリド(acetamiprid)、アセトプロール(acetoprole)、アセフェート(acephate)、アバメクチン(abamectin)、アベルメクチン(avermectin-B)、アミドフルメット(amidoflumet)、アミトラズ(amitraz)、アラニカルブ(alanycarb)、アルジカルブ(aldicarb)、アルドキシカルブ(aldoxycarb)、アルドリン(aldrin)、アルファーエンドスルファン(alpha-endosulfan)、アルファシペルメトリン(alpha-cypermethrin)、アルベンダゾール(albendazole)、アレスリン(allethrin)、イサゾホス(isazofos)、イサミドホス(isamidofos)、イソアミドホス(isoamidofos)、イソキサチオン(isoxathion)、イソフェンホス(isofenphos)、イソプロカルブ(isoprocarb: MIPC)、イベルメクチン(ivermectin)、イミシアホス(imicyafos)、イミダクロプリド(imidac1oprid)、イミプロトリン(imiprothrin)、インドキサカルブ(indoxacarb)、エスフェンバレレート(esfenvalerate)、エチオフェンカルブ(ethiofencarb)、エチオン(ethion)、エチプロール(ethiprole)、エトキサゾール(etoxazole)、エトフェンプロックス(ethofenprox)、エトプロホス(ethoprophos)、エトリムホス(etrimfos)、エマメクチン(emamectin)、エマメクチンベンゾエート(emamectin-benzoate)、エンドスルファン(endosulfan)、エンペントリン(empenthrin)、
capitis)等のPediculus類、ケジラミ(Pthirus pubis)等のPhtirus類、ウシジラミ(Haematopinus eurysternus)、ブタジラミ(Haematopinus suis)等のHaematopinus類、ヒツジジラミ(Damalinia ovis)、ダマリニア・ボビス(Damalinia bovis)等のDamalinia類、ウシホソジラミ(Linognathus vituli)、ヒツジ体幹寄生ホソジラミ(Linognathus ovillus)等のLinognathus類、ケブカウシジラミ(Solenopotes capillatus)等のSolenopotes類等が挙げられる。
本発明化合物 10部
キシレン 70部
N‐メチルピロリドン 10部
ポリオキシエチレンノニルフェニルエーテルと
アルキルベンゼンスルホン酸カルシウムとの混合 10部
以上を均一に混合溶解して乳剤とする。
本発明化合物 3部
クレー粉末 82部
珪藻土粉末 15部
以上を均一に混合粉砕して粉剤とする。
本発明化合物 5部
ベントナイトとクレーの混合粉末 90部
リグニンスルホン酸カルシウム 5部
以上を均一に混合し、適量の水を加えて混練し、造粒、乾燥して粒剤とする。
本発明化合物 20部
カオリンと合成高分散珪酸 75部
ポリオキシエチレンノニルフェニルエーテルと
アルキルベンゼンスルホン酸カルシウムとの混合 5部
以上を均一に混合粉砕して水和剤とする。
試験例1.
モモアカアブラムシ(Myzus persicae)に対する防除価試験
直径8cm、高さ8cmのプラスチックポットにハクサイを植えてモモアカアブラムシを繁殖させ、それぞれのポットの寄生虫数を調査した。本発明の一般式(1)で表される縮合複素環化合物又はその塩類を水に分散させて500ppmの薬液に希釈し、該薬液をポット植えハクサイの茎葉に散布して風乾後、ポットを温室に保管し、薬剤散布後6日目にそれぞれのハクサイに寄生しているモモアカアブラムシの寄生虫数を調査し、下記の式より防除価を算出し、下記判定基準に従って判定した。
T :処理区の散布後寄生虫数
Ca:無処理区の散布前寄生虫数
C:無処理区の散布後寄生虫数
A・・・防除価100%
B・・・防除価99%〜90%
C・・・防除価89%〜80%
D・・・防除価79%〜50%
本発明の一般式(1)で表される縮合複素環化合物又はその塩類を水に分散させて500ppmの薬液に希釈し、該薬液にイネ実生(品種:日本晴)を30秒間浸漬し、風乾した後にガラス試験管に入れ、ヒメトビウンカ3令を各10頭ずつ接種した後に綿栓をし、接種8日後に生死虫数を調査し、補正死虫率を下記の式より算出し、下記の判定基準に従って判定を行った。
A・・・補正死虫率100%
B・・・補正死虫率99%〜90%
C・・・補正死虫率89%〜80%
D・・・補正死虫率79%〜50%
ハクサイ実生にコナガの成虫を放飼して産卵させ、放飼2日後に産下卵の付いたハクサイ実生を本発明の一般式(1)で表される縮合複素環化合物を有効成分とする薬剤を500ppmに希釈した薬液に約30秒間浸漬し、風乾後に25℃の恒温室に静置した。薬液浸漬6日後に孵化虫数を調査し、下記の式により死虫率を算出し、試験例2の判定基準に従って判定を行った。1区10頭3連制。
Claims (8)
- 一般式(1):
(a2) シアノ基;
(a3)(C1-C6)アルキル基;
(a4)(C3-C6)シクロアルキル基;
(a5)(C2-C6)アルケニル基;
(a6)(C2-C6)アルキニル基;
(a7)(C1-C6)アルキルカルボニル基;又は
(a8)(C1-C6)アルコキシカルボニル基;を示す。
R2は、 (b1) 水素原子;
(b2)(C1-C6)アルキル基;
(b3)(C1-C6)アルキルカルボニル基;
(b4)(C1-C6)アルコキシカルボニル基;
(b5)ハロ(C1-C6)アルコキシ基;
(b6)(C1-C6)アルコキシ(C1-C6)アルキル基;
(b7)(C1-C6)アルキルチオ(C1-C6)アルキル基;
(b8)(C2-C6)アルケニル基;
(b9)(C2-C6)アルキニル基;又は
(b10) シクロ(C3-C6)アルキル(C1-C6)アルキル基;を示す。
R3は、
(c1) 水素原子;
(c2) ハロゲン原子;
(c3) シアノ基;
(c4) ニトロ基;
(c5)(C1-C6)アルキル基;
(c6)(C3-C6)シクロアルキル基;
(c7) シアノ(C3-C6)シクロアルキル基;
(c8)(C1-C6)アルコキシ基;
(c9) ハロ(C1-C6)アルキル基;
(c10) ハロ(C1-C6)アルコキシ基;
(c11)(C1-C6)アルキルチオ基;
(c12) ハロ(C1-C6)アルキルチオ基;
(c13)(C1-C6)アルキルスルフィニル基;
(c14) ハロ(C1-C6)アルキルスルフィニル基;
(c15)(C1-C6)アルキルスルホニル基;又は
(c16) ハロ(C1-C6)アルキルスルホニル基;を示す。
R4又はR5は、同一又は異なってもよく、
(d1) 水素原子;
(d2) ハロゲン原子;
(d3) シアノ基;
(d4) ニトロ基;
(d4) ホルミル基;
(d5)(C1-C6)アルキル基;
(d6)(C1-C6)アルコキシ基;
(d7)(C3-C6)シクロアルキル基;
(d8) R6(R7)N基(式中、R6及びR7は、同一又は異なっても良く、水素原子、(C1-C6)アルキル基、(C3-C6)シクロアルキル基、(C3-C6)シクロアルキル(C1-C6)アルキル基、ハロ(C1-C6)アルキル基、(C1-C6)アルキルカルボニル基、(C1-C6)アルコキシカルボニル基、フェニル基、又はフェニル(C1-C6)アルキル基を示す。);
(d9) C(R6)=NOR7基(式中、R6及びR7は前記に同じ。);
(d10) ハロ(C1-C6)アルキル基;
(d11) ハロ(C1-C6)アルコキシ基;
(d12)(C1-C6)アルキルチオ基;
(d13) ハロ(C1-C6)アルキルチオ基;
(d14)(C1-C6)アルキルスルフィニル基;
(d15) ハロ(C1-C6)アルキルスルフィニル基;
(d16)(C1-C6)アルキルスルホニル基;
(d17) ハロ(C1-C6)アルキルスルホニル基;
(d18)(C1-C6)アルキルカルボニル基;
(d19) アリール基;
(d20) 同一又は異なっても良く、(a)ハロゲン原子、(b)シアノ基、(c)ニトロ基、(d)ホルミル基、(e)(C1−C6)アルキル基、(f)ハロ(C1−C6)アルキル基、(g)(C1−C6)アルコキシ基、(h)ハロ(C1−C6)アルコキシ基、(i)(C3−C6)シクロアルキル(C1−C6)アルコキシ基、(j)(C1−C6)アルキルチオ基、(k)ハロ(C1−C6)アルキルチオ基、(l)(C1−C6)アルキルスルフィニル基、(m)ハロ(C1−C6)アルキルスルフィニル基、(n)(C1−C6)アルキルスルホニル基、(o)ハロ(C1−C6)アルキルスルホニル基、(p)(C1−C6)アルキルカルボニル基、(q)カルボキシル基、及び(r)(C1−C6)アルコキシカルボニル基から選択される1〜5の置換基を環上に有するアリール基;
(d21) 複素環基;
(d22) 同一又は異なっても良く、(a)ハロゲン原子、(b)シアノ基、(c)ニトロ基、(d)ホルミル基、(e)(C1−C6)アルキル基、(f)ハロ(C1−C6)アルキル基、(g)(C1−C6)アルコキシ基、(h)ハロ(C1−C6)アルコキシ基、(i)(C3−C6)シクロアルキル(C1−C6)アルコキシ基、(j)(C1−C6)アルキルチオ基、(k)ハロ(C1−C6)アルキルチオ基、(l)(C1−C6)アルキルスルフィニル基、(m)ハロ(C1−C6)アルキルスルフィニル基、(n)(C1−C6)アルキルスルホニル基、(o)ハロ(C1−C6)アルキルスルホニル基、(p)(C1−C6)アルキルカルボニル基、(q)カルボキシル基、及び(r)(C1−C6)アルコキシカルボニル基から選択される1〜2の置換基を環上に有する複素環基;
(d23) アリールオキシ基;
(d24) 同一又は異なっても良く、(a)ハロゲン原子、(b)シアノ基、(c)ニトロ基、(d)ホルミル基、(e)(C1−C6)アルキル基、(f)ハロ(C1−C6)アルキル基、(g)(C1−C6)アルコキシ基、(h)ハロ(C1−C6)アルコキシ基、(i)(C3−C6)シクロアルキル(C1−C6)アルコキシ基、(j)(C1−C6)アルキルチオ基、(k)ハロ(C1−C6)アルキルチオ基、(l)(C1−C6)アルキルスルフィニル基、(m)ハロ(C1−C6)アルキルスルフィニル基、(n)(C1−C6)アルキルスルホニル基、(o)ハロ(C1−C6)アルキルスルホニル基、(p)(C1−C6)アルキルカルボニル基、(q)カルボキシル基、及び(r)(C1−C6)アルコキシカルボニル基から選択される1〜5の置換基を環上に有するアリールオキシ基;
(d25) アリール(C1-C6)アルコキシ基;又は
(d26) 同一又は異なっても良く、(a)ハロゲン原子、(b)シアノ基、(c)ニトロ基、(d)ホルミル基、(e)(C1−C6)アルキル基、(f)ハロ(C1−C6)アルキル基、(g)(C1−C6)アルコキシ基、(h)ハロ(C1−C6)アルコキシ基、(i)(C3−C6)シクロアルキル(C1−C6)アルコキシ基、(j)(C1−C6)アルキルチオ基、(k)ハロ(C1−C6)アルキルチオ基、(l)(C1−C6)アルキルスルフィニル基、(m)ハロ(C1−C6)アルキルスルフィニル基、(n)(C1−C6)アルキルスルホニル基、(o)ハロ(C1−C6)アルキルスルホニル基、(p)(C1−C6)アルキルカルボニル基、(q)カルボキシル基、及び(r)(C1−C6)アルコキシカルボニル基から選択される1〜5の置換基を環上に有するアリール(C1-C6)アルコキシ基;を示す。
Aは、窒素原子又はN‐オキサイドを示す。
A1は、窒素原子、N‐オキサイド又はC-R8基を示す(ここでR8は、 (e1) 水素原子; (e2) ハロゲン原子; (e3) シアノ基; (e4) ニトロ基; (e5) ホルミル基; (e6)(C1-C6)アルキル基; 又は (e7)(C1-C6)アルコキシ基;を表す。)。mは0、1または2を示す。}で表される縮合複素環化合物、若しくはそのN-オキサイド、又はその塩類。 - R1が、 (a1) ハロゲン原子;
(a2) シアノ基;
(a3)(C1-C6)アルキル基;
(a5)(C2-C6)アルケニル基; 又は
(a8)(C1-C6)アルコキシカルボニル基;を示し、
R2が、 (b1) 水素原子;
(b2)(C1-C6)アルキル基;
(b3)(C1-C6)アルキルカルボニル基;
(b4)(C1-C6)アルコキシカルボニル基;
(b5)ハロ(C1-C6)アルコキル基;
(b6)(C1-C6)アルコキシ(C1-C6)アルキル基;
(b7)(C1-C6)アルキルチオ(C1-C6)アルキル基;
(b8)(C2-C6)アルケニル基;
(b9)(C2-C6)アルキニル基;又は
(b10) シクロ(C3-C6)アルキル(C1-C6)アルキル基;を示し、
R3が、
(c9) ハロ(C1-C6)アルキル基; を示し、
R4又はR5が、同一又は異なってもよく、
(d2) ハロゲン原子;
(d4) ホルミル基;
(d6)(C1-C6)アルコキシ基;
(d7)(C3-C6)シクロアルキル基;
(d8) R6(R7)N基(式中、R6及びR7は、同一又は異なっても良く、水素原子、(C1-C6)アルキル基、(C3-C6)シクロアルキル基、(C3-C6)シクロアルキル(C1-C6)アルキル基、ハロ(C1-C6)アルキル基、(C1-C6)アルキルカルボニル基、(C1-C6)アルコキシカルボニル基、フェニル基、又はフェニル(C1-C6)アルキル基を示す。)
(d9) C(R6)=NOR7基(式中、R6及びR7は前記に同じ。);
(d10) ハロ(C1-C6)アルキル基;
(d11) ハロ(C1-C6)アルコキシ基;
(d12)(C1-C6)アルキルチオ基;
(d13) ハロ(C1-C6)アルキルチオ基;
(d16)(C1-C6)アルキルスルホニル基;
(d18)(C1-C6)アルキルカルボニル基;
(d20) 同一又は異なっても良く、(a)ハロゲン原子、(b)シアノ基、(c)ニトロ基、(d)ホルミル基、(e)(C1−C6)アルキル基、(f)ハロ(C1−C6)アルキル基、(g)(C1−C6)アルコキシ基、(h)ハロ(C1−C6)アルコキシ基、(i)(C3−C6)シクロアルキル(C1−C6)アルコキシ基、(j)(C1−C6)アルキルチオ基、(k)ハロ(C1−C6)アルキルチオ基、(l)(C1−C6)アルキルスルフィニル基、(m)ハロ(C1−C6)アルキルスルフィニル基、(n)(C1−C6)アルキルスルホニル基、(o)ハロ(C1−C6)アルキルスルホニル基、(p)(C1−C6)アルキルカルボニル基、(q)カルボキシル基、及び(r)(C1−C6)アルコキシカルボニル基から選択される1〜5の置換基を環上に有するアリール基;
(d21) 複素環基;
(d22) 同一又は異なっても良く、(a)ハロゲン原子、(b)シアノ基、(c)ニトロ基、(d)ホルミル基、(e)(C1−C6)アルキル基、(f)ハロ(C1−C6)アルキル基、(g)(C1−C6)アルコキシ基、(h)ハロ(C1−C6)アルコキシ基、(i)(C3−C6)シクロアルキル(C1−C6)アルコキシ基、(j)(C1−C6)アルキルチオ基、(k)ハロ(C1−C6)アルキルチオ基、(l)(C1−C6)アルキルスルフィニル基、(m)ハロ(C1−C6)アルキルスルフィニル基、(n)(C1−C6)アルキルスルホニル基、(o)ハロ(C1−C6)アルキルスルホニル基、(p)(C1−C6)アルキルカルボニル基、(q)カルボキシル基、及び(r)(C1−C6)アルコキシカルボニル基から選択される1〜2の置換基を環上に有する複素環基;
(d24) 同一又は異なっても良く、(a)ハロゲン原子、(b)シアノ基、(c)ニトロ基、(d)ホルミル基、(e)(C1−C6)アルキル基、(f)ハロ(C1−C6)アルキル基、(g)(C1−C6)アルコキシ基、(h)ハロ(C1−C6)アルコキシ基、(i)(C3−C6)シクロアルキル(C1−C6)アルコキシ基、(j)(C1−C6)アルキルチオ基、(k)ハロ(C1−C6)アルキルチオ基、(l)(C1−C6)アルキルスルフィニル基、(m)ハロ(C1−C6)アルキルスルフィニル基、(n)(C1−C6)アルキルスルホニル基、(o)ハロ(C1−C6)アルキルスルホニル基、(p)(C1−C6)アルキルカルボニル基、(q)カルボキシル基、及び(r)(C1−C6)アルコキシカルボニル基から選択される1〜5の置換基を環上に有するアリールオキシ基;
(d25) アリール(C1-C6)アルコキシ基;又は
(d26) 同一又は異なっても良く、(a)ハロゲン原子、(b)シアノ基、(c)ニトロ基、(d)ホルミル基、(e)(C1−C6)アルキル基、(f)ハロ(C1−C6)アルキル基、(g)(C1−C6)アルコキシ基、(h)ハロ(C1−C6)アルコキシ基、(i)(C3−C6)シクロアルキル(C1−C6)アルコキシ基、(j)(C1−C6)アルキルチオ基、(k)ハロ(C1−C6)アルキルチオ基、(l)(C1−C6)アルキルスルフィニル基、(m)ハロ(C1−C6)アルキルスルフィニル基、(n)(C1−C6)アルキルスルホニル基、(o)ハロ(C1−C6)アルキルスルホニル基、(p)(C1−C6)アルキルカルボニル基、(q)カルボキシル基、及び(r)(C1−C6)アルコキシカルボニル基から選択される1〜5の置換基を環上に有するアリール(C1-C6)アルコキシ基; を示す、請求項1に記載の縮合複素環化合物、若しくはそのN-オキサイド、又はその塩類。 - R1が、 (a1) ハロゲン原子;
(a2) シアノ基;
(a3)(C1-C6)アルキル基;
(a5)(C2-C6)アルケニル基; 又は
(a8)(C1-C6)アルコキシカルボニル基;を示し、
R2が、 (b1) 水素原子; (b2)(C1-C6)アルキル基;
(b3)(C1-C6)アルキルカルボニル基;
(b4)(C1-C6)アルコキシカルボニル基;
(b5)ハロ(C1-C6)アルコキル基;
(b6)(C1-C6)アルコキシ(C1-C6)アルキル基;
(b7)(C1-C6)アルキルチオ(C1-C6)アルキル基;
(b8)(C2-C6)アルケニル基;
(b9)(C2-C6)アルキニル基;又は
(b10) シクロ(C3-C6)アルキル(C1-C6)アルキル基;を示し、
R3が、
(c9) ハロ(C1-C6)アルキル基;を示し、
R4又はR5が、同一又は異なってもよく、
(d2) ハロゲン原子;
(d4) ホルミル基;
(d6)(C1-C6)アルコキシ基;
(d7)(C3-C6)シクロアルキル基;
(d9) C(R6)=NOR7基(式中、R6及びR7は、同一又は異なっても良く、水素原子、(C1-C6)アルキル基、(C3-C6)シクロアルキル基、(C3-C6)シクロアルキル(C1-C6)アルキル基、ハロ(C1-C6)アルキル基、(C1-C6)アルキルカルボニル基、(C1-C6)アルコキシカルボニル基、フェニル基、又はフェニル(C1-C6)アルキル基を示す。);
(d10) ハロ(C1-C6)アルキル基;
(d11) ハロ(C1-C6)アルコキシ基;
(d20) 同一又は異なっても良く、(a)ハロゲン原子、(b)シアノ基、(c)ニトロ基、(d)ホルミル基、(e)(C1−C6)アルキル基、(f)ハロ(C1−C6)アルキル基、(g)(C1−C6)アルコキシ基、(h)ハロ(C1−C6)アルコキシ基、(i)(C3−C6)シクロアルキル(C1−C6)アルコキシ基、(j)(C1−C6)アルキルチオ基、(k)ハロ(C1−C6)アルキルチオ基、(l)(C1−C6)アルキルスルフィニル基、(m)ハロ(C1−C6)アルキルスルフィニル基、(n)(C1−C6)アルキルスルホニル基、(o)ハロ(C1−C6)アルキルスルホニル基、(p)(C1−C6)アルキルカルボニル基、(q)カルボキシル基、及び(r)(C1−C6)アルコキシカルボニル基から選択される1〜5の置換基を環上に有するアリール基;
(d21) 複素環基;
(d22) 同一又は異なっても良く、(a)ハロゲン原子、(b)シアノ基、(c)ニトロ基、(d)ホルミル基、(e)(C1−C6)アルキル基、(f)ハロ(C1−C6)アルキル基、(g)(C1−C6)アルコキシ基、(h)ハロ(C1−C6)アルコキシ基、(i)(C3−C6)シクロアルキル(C1−C6)アルコキシ基、(j)(C1−C6)アルキルチオ基、(k)ハロ(C1−C6)アルキルチオ基、(l)(C1−C6)アルキルスルフィニル基、(m)ハロ(C1−C6)アルキルスルフィニル基、(n)(C1−C6)アルキルスルホニル基、(o)ハロ(C1−C6)アルキルスルホニル基、(p)(C1−C6)アルキルカルボニル基、(q)カルボキシル基、及び(r)(C1−C6)アルコキシカルボニル基から選択される1〜2の置換基を環上に有する複素環基;
(d24) 同一又は異なっても良く、(a)ハロゲン原子、(b)シアノ基、(c)ニトロ基、(d)ホルミル基、(e)(C1−C6)アルキル基、(f)ハロ(C1−C6)アルキル基、(g)(C1−C6)アルコキシ基、(h)ハロ(C1−C6)アルコキシ基、(i)(C3−C6)シクロアルキル(C1−C6)アルコキシ基、(j)(C1−C6)アルキルチオ基、(k)ハロ(C1−C6)アルキルチオ基、(l)(C1−C6)アルキルスルフィニル基、(m)ハロ(C1−C6)アルキルスルフィニル基、(n)(C1−C6)アルキルスルホニル基、(o)ハロ(C1−C6)アルキルスルホニル基、(p)(C1−C6)アルキルカルボニル基、(q)カルボキシル基、及び(r)(C1−C6)アルコキシカルボニル基から選択される1〜5の置換基を環上に有するアリールオキシ基;
(d25) アリール(C1-C6)アルコキシ基;又は
(d26) 同一又は異なっても良く、(a)ハロゲン原子、(b)シアノ基、(c)ニトロ基、(d)ホルミル基、(e)(C1−C6)アルキル基、(f)ハロ(C1−C6)アルキル基、(g)(C1−C6)アルコキシ基、(h)ハロ(C1−C6)アルコキシ基、(i)(C3−C6)シクロアルキル(C1−C6)アルコキシ基、(j)(C1−C6)アルキルチオ基、(k)ハロ(C1−C6)アルキルチオ基、(l)(C1−C6)アルキルスルフィニル基、(m)ハロ(C1−C6)アルキルスルフィニル基、(n)(C1−C6)アルキルスルホニル基、(o)ハロ(C1−C6)アルキルスルホニル基、(p)(C1−C6)アルキルカルボニル基、(q)カルボキシル基、及び(r)(C1−C6)アルコキシカルボニル基から選択される1〜5の置換基を環上に有するアリール(C1-C6)アルコキシ基;を示す、請求項1に記載の縮合複素環化合物、若しくはそのN-オキサイド、又はその塩類。 - 請求項1乃至3の何れか1項に記載の縮合複素環化合物、若しくはそのN-オキサイド、又はその塩類の農園芸用殺虫剤としての使用。
- 請求項4に記載の農園芸用殺虫剤の有効成分で植物又は土壌を処理することを特徴とする農園芸用殺虫剤の使用方法。
- 請求項4に記載の農園芸用殺虫剤の有効量で植物又は土壌を処理することを特徴とする農園芸用害虫の防除方法。
- 請求項1乃至3の何れか1項に記載の縮合複素環化合物、若しくはそのN-オキサイド、又はその塩類を有効成分として含有することをと特徴とする動物用の外部寄生虫防除剤。
- 請求項7に記載の動物用の外部寄生虫防除剤の有効量で動物の外部寄生虫を処理することを特徴とする動物用外部寄生虫の防除方法。
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BR112019019172B1 (pt) * | 2017-03-23 | 2023-03-07 | Sumitomo Chemical Company, Limited | Composto heterocíclico fundido, composição contendo o mesmo e método para o controle de um artrópode nocivo |
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EP3835301B1 (en) * | 2018-07-10 | 2024-10-09 | Nihon Nohyaku Co., Ltd. | Benzimidazole compound having alkylenedioxy group which may be halogenated or salt thereof, agricultural and horticultural pesticide containing said compound, and method of using same |
US12116370B2 (en) | 2019-05-27 | 2024-10-15 | Nihon Nohyaku Co., Ltd. | Condensed heterocyclic compound having a bridgehead nitrogen atom or salt thereof, agricultural or horticultural insecticide comprising the compound, and method for using the insecticide |
US20220361499A1 (en) * | 2019-09-12 | 2022-11-17 | Nihon Nohyaku Co., Ltd. | Agricultural or horticultural insecticide or animal ectoparasite or endoparasite control agent each comprising a condensed heterocyclic compound having a substituted cyclopropane-oxadiazole group or a salt thereof as active ingredient, and method for using the insecticide or the control agent |
WO2024175558A1 (en) | 2023-02-23 | 2024-08-29 | Boehringer Ingelheim Vetmedica Gmbh | Cyclopropyl-(hetero)aryl-substituted ethyl-sulfone/sulfoximine-pyridine n-oxide derivatives |
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US10779537B2 (en) | 2020-09-22 |
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CN109843864A (zh) | 2019-06-04 |
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AU2017342576B2 (en) | 2020-02-27 |
WO2018070502A1 (ja) | 2018-04-19 |
RU2752171C2 (ru) | 2021-07-23 |
JPWO2018070502A1 (ja) | 2019-09-05 |
EP3527560A1 (en) | 2019-08-21 |
MX2019003932A (es) | 2019-06-10 |
BR112019006217A2 (pt) | 2019-06-25 |
CA3038482A1 (en) | 2018-04-19 |
KR102216655B1 (ko) | 2021-02-16 |
KR20190047067A (ko) | 2019-05-07 |
ZA201902421B (en) | 2020-08-26 |
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