JP5868957B2 - 殺虫剤としてのチアゾール誘導体 - Google Patents
殺虫剤としてのチアゾール誘導体 Download PDFInfo
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- JP5868957B2 JP5868957B2 JP2013508460A JP2013508460A JP5868957B2 JP 5868957 B2 JP5868957 B2 JP 5868957B2 JP 2013508460 A JP2013508460 A JP 2013508460A JP 2013508460 A JP2013508460 A JP 2013508460A JP 5868957 B2 JP5868957 B2 JP 5868957B2
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- NWWZPOKUUAIXIW-FLIBITNWSA-N thiamethoxam Chemical compound [O-][N+](=O)\N=C/1N(C)COCN\1CC1=CN=C(Cl)S1 NWWZPOKUUAIXIW-FLIBITNWSA-N 0.000 description 1
- 125000004305 thiazinyl group Chemical group S1NC(=CC=C1)* 0.000 description 1
- BAKXBZPQTXCKRR-UHFFFAOYSA-N thiodicarb Chemical compound CSC(C)=NOC(=O)NSNC(=O)ON=C(C)SC BAKXBZPQTXCKRR-UHFFFAOYSA-N 0.000 description 1
- OPASCBHCTNRLRM-UHFFFAOYSA-N thiometon Chemical compound CCSCCSP(=S)(OC)OC OPASCBHCTNRLRM-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
- 229960002447 thiram Drugs 0.000 description 1
- KUAZQDVKQLNFPE-UHFFFAOYSA-N thiram Chemical compound CN(C)C(=S)SSC(=S)N(C)C KUAZQDVKQLNFPE-UHFFFAOYSA-N 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-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
- HYVWIQDYBVKITD-UHFFFAOYSA-N tolylfluanid Chemical compound CN(C)S(=O)(=O)N(SC(F)(Cl)Cl)C1=CC=C(C)C=C1 HYVWIQDYBVKITD-UHFFFAOYSA-N 0.000 description 1
- 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
- DDVNRFNDOPPVQJ-HQJQHLMTSA-N transfluthrin Chemical compound CC1(C)[C@H](C=C(Cl)Cl)[C@H]1C(=O)OCC1=C(F)C(F)=CC(F)=C1F DDVNRFNDOPPVQJ-HQJQHLMTSA-N 0.000 description 1
- 230000014616 translation Effects 0.000 description 1
- 230000005068 transpiration Effects 0.000 description 1
- AMFGTOFWMRQMEM-UHFFFAOYSA-N triazophos Chemical compound N1=C(OP(=S)(OCC)OCC)N=CN1C1=CC=CC=C1 AMFGTOFWMRQMEM-UHFFFAOYSA-N 0.000 description 1
- IQGKIPDJXCAMSM-UHFFFAOYSA-N triazoxide Chemical compound N=1C2=CC=C(Cl)C=C2[N+]([O-])=NC=1N1C=CN=C1 IQGKIPDJXCAMSM-UHFFFAOYSA-N 0.000 description 1
- 229940116861 trichinella britovi Drugs 0.000 description 1
- 229940096911 trichinella spiralis Drugs 0.000 description 1
- NFACJZMKEDPNKN-UHFFFAOYSA-N trichlorfon Chemical compound COP(=O)(OC)C(O)C(Cl)(Cl)Cl NFACJZMKEDPNKN-UHFFFAOYSA-N 0.000 description 1
- 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
- XAIPTRIXGHTTNT-UHFFFAOYSA-N triflumuron Chemical compound C1=CC(OC(F)(F)F)=CC=C1NC(=O)NC(=O)C1=CC=CC=C1Cl XAIPTRIXGHTTNT-UHFFFAOYSA-N 0.000 description 1
- 238000002211 ultraviolet spectrum Methods 0.000 description 1
- YNWVFADWVLCOPU-MAUPQMMJSA-N uniconazole P Chemical compound C1=NC=NN1/C([C@@H](O)C(C)(C)C)=C/C1=CC=C(Cl)C=C1 YNWVFADWVLCOPU-MAUPQMMJSA-N 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
- JARYYMUOCXVXNK-CSLFJTBJSA-N validamycin A 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-CSLFJTBJSA-N 0.000 description 1
- LESVOLZBIFDZGS-UHFFFAOYSA-N vamidothion Chemical compound CNC(=O)C(C)SCCSP(=O)(OC)OC LESVOLZBIFDZGS-UHFFFAOYSA-N 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 230000003253 viricidal effect Effects 0.000 description 1
- 239000000664 voltage gated sodium channel blocking agent Substances 0.000 description 1
- BCEHBSKCWLPMDN-MGPLVRAMSA-N voriconazole Chemical compound C1([C@H](C)[C@](O)(CN2N=CN=C2)C=2C(=CC(F)=CC=2)F)=NC=NC=C1F BCEHBSKCWLPMDN-MGPLVRAMSA-N 0.000 description 1
- 229960004740 voriconazole Drugs 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- WCJYTPVNMWIZCG-UHFFFAOYSA-N xylylcarb Chemical compound CNC(=O)OC1=CC=C(C)C(C)=C1 WCJYTPVNMWIZCG-UHFFFAOYSA-N 0.000 description 1
- 239000005943 zeta-Cypermethrin Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229940048462 zinc phosphide Drugs 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
- FJBGIXKIXPUXBY-UHFFFAOYSA-N {2-[3-(4-chlorophenyl)propyl]-2,4,4-trimethyl-1,3-oxazolidin-3-yl}(imidazol-1-yl)methanone Chemical compound C1=CN=CN1C(=O)N1C(C)(C)COC1(C)CCCC1=CC=C(Cl)C=C1 FJBGIXKIXPUXBY-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero 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
- A01N43/72—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
- A01N43/74—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 1,3
- A01N43/78—1,3-Thiazoles; Hydrogenated 1,3-thiazoles
Description
G1は、N、CHまたはC−ハロゲンを表し、
G2は、
R1は、シアノ、ニトロまたはハロゲンを表し、および
G3は、ジオキサニル、オキサゾリニル、ジヒドロオキサジアジニル、ジヒドロジオキサジニルおよびヒドロキシピリジルからなる群からの置換ヘテロ環を表し、または
G3は、トリアゾリノニル、ジヒドロジオキサジニル、ジヒドロオキサジアジニル、ジオキソラニル、ジオキサニル(特に1,3−ジオキサン−2−イル)、ピペリジノニル、ピロリジノニルおよびピラゾリノニルからなる群からの必要に応じて置換されたヘテロシクリルにより、必要に応じて置換されたフェニル、必要に応じて置換されたヘテロアリールまたは必要に応じて置換されたヘテロアリールアルキルにより置換されたヘテロアリールを表す)
を表す〕
で示される新規化合物および式(I)で示される化合物の塩、金属錯体およびN−オキシドにより解消される。
G1は、N、CHまたはC−ハロゲンを表し、
G2は、
R1は、シアノ、ニトロ、フッ素、塩素、臭素およびヨウ素からなる群からの基を表し、
G3は、ハロゲン、シアノ、ニトロ、アルキル、ハロアルキル、シクロアルキル、アルコキシ、ハロアルコキシ、アルキルチオ、ハロアルキルチオ、アルキルスルフィニル、アルキルスルホニル、ハロアルキルスルフィニル、ハロアルキルスルホニル、アミノ、アルキルアミノ、ジアルキルアミノ、アルキルカルボニルアミノ、アルコキシカルボニルアミノ、アルコキシアルキル、ハロアルコキシアルキル、アルケニル、アルキニル、シクロアルキルアルキル、アルキルカルボニル、アルコキシカルボニル、アミノカルボニル、ピリジルおよびピリミジルからなる群からの1以上の基で置換されたジオキサニル、オキサゾリニル、ジヒドロオキサジアジニル、ジヒドロジオキサジニルおよびヒドロキシピリジルからなる群からのヘテロシクリルを表し、
また、G3は、ピロリル、ピラゾリル、イミダゾリル、1,2,3−トリアゾリル、1,2,4−トリアゾリル、オキサゾリル、イソオキサゾリル、チアゾリル、イソチアゾリル、1,2,3−オキサジアゾリル、1,2,4−オキサジアゾリル、1,3,4−オキサジアゾリル、1,2,5−オキサジアゾリル、1,2,3−チアジアゾリル、1,2,4−チアジアゾリル、1,3,4−チアジアゾリル、1,2,5−チアジアゾリル、ピリジル、ピリミジニル、ピリダジニル、ピラジニル、1,2,3−トリアジニル、1,2,4−トリアジニル、1,3,5−トリアジニル、ベンゾフリル、ベンゾイソフリル、ベンゾチエニル、ベンゾイソチエニル、インドリル、イソインドリル、インダゾリル、ベンゾチアゾリル、ベンゾイソチアゾリル、ベンゾオキサゾリル、ベンゾイソオキサゾリル、ベンゾイミダゾリル、2,1,3−ベンゾオキサジアゾール、キノリニル、イソキノリニル、シンノリニル、フタラジニル、キナゾリニル、キノキサリニル、ナフチリジニル、ベンゾトリアジニル、プリニル、プテリジニルおよびインドリジニル、特に、ピリジル、ピリミジル、イミダゾリル、ピラゾリル、トリアジニル、チアゾリル、チアジアゾリル、オキサジアゾリルおよびオキサゾリルからなる群からのヘテロアリールを表し、それぞれ、トリアゾリノニル、ジヒドロジオキサジニル、ジヒドロオキサジアジニル、ジオキソラニル、ジオキサニル(特に1,3−ジオキサン−2−イル)、ピペリジノニル、ピロリジノニルおよびピラゾリノニル(これらは、その部分についてアルキルまたはハロアルキルで置換されていてもよい)からなる群からのヘテロシクリル基により、フェニル(これは、その部分についてハロゲン、シアノ、ニトロ、アルキルおよびハロアルキルで置換されていてもよい)により、ピロリル、ピリジル、ピリジル、N−オキシド、ピリミジル、イミダゾリル、ピラゾリル、オキサゾリル、チアゾリル、フラニル、チエニル、トリアゾリル、オキサジアゾリル、チアジアゾリル、ピラジニル、トリアジニル、テトラジニルおよびイソキノリニル(これらは、その部分について、ハロゲン、ニトロ、アルキル、ハロアルキル、アルコキシ、ハロアルコキシ、アルコキシアルキル、アルキルチオ、アルキルチオアルキルおよびシクロアルキルで置換されていてもよい)により、またはトリアゾリルアルキル、ピリジルアルキル、ピリミジルアルキルおよびオキサジアゾリルアルキルからなる群からのヘテロアリールアルキル基(これらは、その部分についてアルキルで置換されていてもよい)により置換されている)
を表す〕
で示される化合物である。
G1は、N、CHまたはC−ハロゲン(C−ハロゲンの場合には、特にC−F、C−ClまたはC−Br)を表し、
G2は、
R1は、シアノ、フッ素または塩素を表し、
G3は、ハロゲン、シアノ、ニトロ、C1−C6−アルキル、C1−C6−ハロアルキル、C3−C6−シクロアルキル、C1−C6−アルコキシ、C1−C6−ハロアルコキシ、C1−C6−アルキルチオ、C1−C6−ハロアルキルチオ、C1−C6−アルキルスルフィニル、C1−C6−アルキルスルホニル、C1−C6−ハロアルキルスルフィニル、C1−C6−ハロアルキルスルホニル、アミノ−、C1−C6−アルキルアミノ、ジ(C1−C6−アルキル)アミノ、C1−C6−アルキルカルボニルアミノ、C1−C6−アルコキシカルボニルアミノ、C1−C6−アルコキシ−C1−C6−アルキル、C1−C6−ハロアルコキシ−C1−C6−アルキル、C2−C6−アルケニル、C2−C6−アルキニル、C3−C6−シクロアルキル−C1−C6−アルキル、C1−C6−アルキルカルボニル、C1−C6−アルコキシカルボニル、アミノカルボニル、ピリジルおよびピリミジルからなる群からの1以上の置換基により1,3−ジオキサン−2−イル、オキサゾリニル、ジヒドロオキサジアジニル、ジヒドロジオキサジニルおよびヒドロキシピリジルからなる群からのヘテロシクリルを表し、
また、G3は、ピロリル、ピラゾリル、イミダゾリル、1,2,3−トリアゾリル、1,2,4−トリアゾリル、オキサゾリル、イソオキサゾリル、チアゾリル、イソチアゾリル、1,2,3−オキサジアゾリル、1,2,4−オキサジアゾリル、1,3,4−オキサジアゾリル、1,2,5−オキサジアゾリル、1,2,3−チアジアゾリル、1,2,4−チアジアゾリル、1,3,4−チアジアゾリル、1,2,5−チアジアゾリル、ピリジル、ピリミジニル、ピリダジニル、ピラジニル、1,2,3−トリアジニル、1,2,4−トリアジニル、1,3,5−トリアジニル、ベンゾフリル、ベンゾイソフリル、ベンゾチエニル、ベンゾイソチエニル、インドリル、イソインドリル、インダゾリル、ベンゾチアゾリル、ベンゾイソチアゾリル、ベンゾオキサゾリル、ベンズイソオキサゾリル、ベンズイミダゾリル、2,1,3−ベンゾオキサジアゾール、キノリニル、イソキノリニル、シンノリニル、フタラジニル、キナゾリニル、キノキサリニル、ナフチリジニル、ベンゾトリアジニル、プリニル、プテリジニルおよびインドリジニル(特に、ピリジル、ピリミジル、イミダゾリル、ピラゾリル、トリアジニル、チアゾリル、チアジアゾリル、オキサジアゾリルおよびオキサゾリル)からなる群からのヘテロアリールを表し、これらは、モルフォニル、トリアゾリノニル、ジヒドロジオキサジニル、ジヒドロオキサジアジニル、ジオキソラニル、ジオキサニル、ピペリジノニル、ピロリジノニルおよびピラゾリノニル(これらは、その部分についてC1−C6−アルキルまたはC1−C6−ハロアルキルで置換されていてもよい)により、フェニル(これは、その部分についてハロゲン、シアノ、ニトロ、C1−C6−アルキルおよびC1−C6−ハロアルキルで置換されていてもよい)により、ピロリル、ピリジル、ピリジル、N−オキシド、ピリミジル、イミダゾリル、ピラゾリル、オキサゾリル、チアゾリル、フラニル、チエニル、トリアゾリル、オキサジアゾリル、チアジアゾリル、ピラジニル、トリアジニル、テトラジニルおよびイソキノリニル(これらは、その部分について、ハロゲン、ニトロ、C1−C6−アルキル、C1−C6−ハロアルキル、C1−C6−アルコキシ、C1−C6−ハロアルコキシ、C1−C6−アルコキシ−C1−C6−アルキル、C1−C6−アルキルチオ、C1−C6−アルキルチオ−C1−C6−アルキルおよびC3−C6−シクロアルキルで置換されていてもよい)により、またはトリアゾリル−C1−C4−アルキル、ピリジル−C1−C4−アルキル、ピリミジル−C1−C4−アルキルおよびオキサジアゾリル−C1−C4−アルキルからなる群からのヘテロアリールアルキル基(これらは、その部分についてアルキルで置換されていてもよい)により置換されている)
を表す〕
で示される化合物である。
G1は、N、CHまたはC−ハロゲン(C−ハロゲンの場合には、特にC−FまたはC−Cl)を表し、
G2は、
R1は、シアノ、フッ素または塩素を表し、
G3は、ハロゲン、シアノ、ニトロ、C1−C4−アルキル、C1−C4−ハロアルキル、C3−C6−シクロアルキル、C1−C4−アルコキシ、C1−C4−ハロアルコキシ、C1−C4−アルキルチオ、C1−C4−ハロアルキルチオ、C1−C4−アルキルスルフィニル、C1−C4−アルキルスルホニル、C1−C4−ハロアルキルスルフィニル、C1−C4−ハロアルキルスルホニル、アミノ、C1−C4−アルキルアミノ、ジ(C1−C4−アルキル)アミノ、C1−C4−アルキルカルボニルアミノ、C1−C4−アルコキシカルボニルアミノ、C1−C4−アルコキシ−C1−C4−アルキル、C1−C4−ハロアルコキシ−C1−C4−アルキル、C2−C4−アルケニル、C2−C4−アルキニル、C3−C6−シクロアルキル−C1−C4−アルキル、C1−C4−アルキルカルボニル、C1−C4−アルコキシカルボニル、アミノカルボニル、ピリジルおよびピリミジルからなる群からの1以上の置換基により置換されている1,3−ジオキサン−2−イル、オキサゾリニル、ジヒドロオキサジアジニル、ジヒドロジオキサジニルおよびヒドロキシピリジルからなる群からのヘテロシクリルを表し、
また、G3は、ピロリル、ピラゾリル、イミダゾリル、1,2,3−トリアゾリル、1,2,4−トリアゾリル、オキサゾリル、イソオキサゾリル、チアゾリル、イソチアゾリル、1,2,3−オキサジアゾリル、1,2,4−オキサジアゾリル、1,3,4−オキサジアゾリル、1,2,5−オキサジアゾリル、1,2,3−チアジアゾリル、1,2,4−チアジアゾリル、1,3,4−チアジアゾリル、1,2,5−チアジアゾリル、ピリジル、ピリミジニル、ピリダジニル、ピラジニル、1,2,3−トリアジニル、1,2,4−トリアジニル、1,3,5−トリアジニル、ベンゾフリル、ベンゾイソフリル、ベンゾチエニル、ベンゾイソチエニル、インドリル、イソインドリル、インダゾリル、ベンゾチアゾリル、ベンゾイソチアゾリル、ベンゾオキサゾリル、ベンズイソオキサゾリル、ベンズイミダゾリル、2,1,3−ベンゾオキサジアゾール、キノリニル、イソキノリニル、シンノリニル、フタラジニル、キナゾリニル、キノキサリニル、ナフチリジニル、ベンゾトリアジニル、プリニル、プテリジニルおよびインドリジニル(特に、ピリジル、ピリミジル、イミダゾリル、ピラゾリル、トリアジニル、チアゾリル、チアジアゾリル、オキサジアゾリルおよびオキサゾリル)からなる群からのヘテロシクリルを表し、これらは、モルフォニル、トリアゾリノニル、ジヒドロジオキサジニル、ジヒドロオキサジアジニル、ジオキソラニル、ジオキサニル、ピペリジノニル、ピロリジノニルおよびピラゾリノニル(これらは、その部分についてC1−C4−アルキルおよびC1−C4−ハロアルキルで置換されていてもよい)からなる群からのヘテロシクリル基により、フェニル(これは、その部分についてハロゲン、シアノ、ニトロ、C1−C4−アルキルおよびC1−C4−ハロアルキルで置換されていてもよい)により、ピロリル、ピリジル、ピリジル、N−オキシド、ピリミジル、イミダゾリル、ピラゾリル、オキサゾリル、チアゾリル、フラニル、チエニル、トリアゾリル、オキサジアゾリル、チアジアゾリル、ピラジニル、トリアジニル、テトラジニルおよびイソキノリニル(これらは、その部分について、ハロゲン、ニトロ、C1−C4−アルキル、C1−C4−ハロアルキル、C1−C4−アルコキシ、C1−C4−ハロアルコキシ、C1−C4−アルコキシ−C1−C4−アルキル、C1−C4−アルキルチオ、C1−C4−アルキルチオ−C1−C4−アルキルおよびC3−C6−シクロアルキルで置換されていてもよい)により、またはトリアゾリル−C1−C4−アルキル、ピリジル−C1−C4−アルキル、ピリミジル−C1−C4−アルキルおよびオキサジアゾリル−C1−C4−アルキルからなる群からのヘテロアリールアルキル基(これらは、その部分についてアルキルで置換されていてもよい)により置換されている)
を表す〕
で示される化合物である。
G1は、N、CHまたはC−ハロゲン(C−ハロゲンの場合には、特にC−F)を表し、
G2は、
R1は、フッ素または塩素を表し、
G3は、何れの場合にも必要に応じてピリジル−またはピリミジニル−で置換された1,3−ジオキサン−2−イル、オキサゾリニル、ジヒドロオキサジアジニルまたはヒドロキシピリジルを表し、
また、G3は、ピラゾリル、1,2,4−オキサジアゾリル、ピリジル、ピリミジニル、1,3,5−トリアジニル、トリアジニルおよびオキサジアゾリルからなる群からのヘテロアリール基を表し、これらは、モルフォニル、トリアゾリノニル、ジヒドロジオキサジニル、ジヒドロオキサジアジニル、ピペリジノニル、ピロリジノニルおよびピラゾリノニル(これらは、その部分についてC1−C4−アルキル(特にメチル)およびC1−C4−ハロアルキル(特にCF3)で置換されていてもよい)からなる群からのヘテロシクリル基により、フェニル(これは、その部分についてハロゲン(特にフッ素、塩素)により置換されていてもよい)により、ピロリル、ピリジル(特に2−ピリジル)、ピリジルN−オキシド、ピリミジル(特に2−ピリミジニル)、ピラゾリル(特に1−ピラゾリルおよび3−ピラゾリル)、チアゾリル、フラニル、チエニル、トリアゾリル、オキサジアゾリル、チアジアゾリル(特に1,2,4−チアジアゾル−3−イル)、ピラジニル、トリアジニルおよびイソキノリニル(これらは、その部分について、ハロゲン(特にフッ素、塩素)、ニトロ、C1−C4−アルキル(特にメチル、エチル、n−プロピル、イソプロピル、tert−ブチル)、C1−C4−ハロアルキル(特にCF3、CHF2、CFClH)、C1−C4−アルコキシ(特にメトキシ、エトキシ)、C3−C6−シクロアルキル(特にシクロプロピル、シクロブチル、シクロペンチル)で置換されていてもよい)により、またはトリアゾリル−C1−C4−アルキル(特にトリアゾリルメチル)、ピリジル−C1−C4−アルキル(特にピリジルメチル)およびオキサジアゾリル−C1−C4−アルキル(特にオキサジアゾリルメチル)からなる群からのヘテロアリールアルキル基(これらは、その部分についてアルキルで置換されていてもよい)により置換されている)
を表す〕
で示される化合物である。
本発明は、純粋異性体にも、異性体混合物にも関する。
例えばアンモニウム塩および粉砕された天然鉱物、例えばカオリン、クレー、タルク、チョーク、石英、アタパルジャイト、モンモリロナイトまたはケイ藻土および粉砕された合成鉱物、例えば高度に分散したシリカ、アルミナおよびシリケート等:粒剤のための適当な固体担体は、例えば粉砕して分画した天然石等、例えば方解石、大理石、軽石、海泡石および苦灰岩等、および無機および有機の粗びき粉の合成顆粒、および有機材料、例えば紙、おがくず、ココナッツ殻、トウモロコシ穂軸およびタバコの葉柄等の顆粒等であり;適切な乳化剤および/またはフォーム形成剤は、例えば非イオン性およびアニオン性の乳化剤、例えばポリオキシエチレン脂肪酸エステル、ポリオキシエチレン脂肪アルコールエーテル、例えばアルキルアリールポリグリコールエーテル、アルキルスルホネート、アルキルスルフェート、アリールスルホネートおよびタンパク質加水分解物等であり;適切な分散剤は、非イオン性及び/又はイオン性の物質、例えばアルコール−POE及び/又は−POPエーテル、酸及び/又はPOP−POEエステル、アルキルアリール及び/又はPOP/POEエーテル、脂肪及び/又はPOP/POE付加物、POE−及び/又はPOP−ポリオール誘導体、POE−及び/又はPOP−ソルビタンまたは糖付加体、アルキルスルフェートまたはアリールスルフェート、アルキルスルホネートまたはアリールスルホネート類及びアルキルホスフェート類若しくはアリールホスフェートまたは対応するPOエーテル付加物からのものである。さらに、適切なオリゴマーまたはポリマー、例えばビニルモノマーから誘導されたもの、アクリル酸から誘導されたもの、EO及び/又はPOの単独又は例えば(ポリ)アルコールまたは(ポリ)アミンと組み合わせたものから誘導されたもの。また、リグニン及びそのスルホン酸誘導体、未変性セルロース及び変性セルロース、芳香族及び/又は脂肪族スルホン酸およびそれらのホルムアルデヒドとの付加体なども使用することができる。
ここでその共通名称により確認されている活性化合物は、既知であり、例えば害虫ハンドブック(「The Pesticide Manual」、第14版、英国作物保護協議会、2006年)において記載され、インターネット(例えばhttp://www.alanwood.net/pesticides)上に見出すことができる。
クロペンチル異性体、ビオレスメトリン、シクロプロトリン、シフルトリン、ベータ-シフルトリン、シハロトリン、ラムダ-シハロトリン、ガンマ-シハロトリン、シペルメトリン、アルファ-シペルメトリン、ベータ-シペルメトリン、シータ-シペルメトリン、ゼータ-シペルメトリン[(1R)−トランス−異性体]、デルタメトリン、エムペントリン[(EZ)−(1R)−異性体]、エスフェンバレレート、エトフェンプロックス、フェンプロパトリン、フェンバレレート、フルシトリネート、フルメトリン、タウ-フルバリネート、ハルフェンプロックス、イミプロトリン、カデトリン、ペルメトリン、フェノトリン[(1R)−トランス−異性体]、プラレトリン、ピレトリン(ピレトラム)、レスメトリン、シラフルオフェン、テフルトリン、テトラメトリン、テトラロメトリン[(1R)−異性体]、トラロメトリンおよびトランスフルトリン;またはDDT;またはメトキシクロル、ZXI8901;
(1)エルゴステロール生合成阻害剤、例えばアルジモルフ、アザコナゾール、ビテルタノール、ブロムコナゾール、シプロコナゾール、ジクロブトラゾール、ジフェノコナゾール、ジニコナゾール、ジニコナゾール−M、ドデモルフ、ドデモルフアセテート、エポキシコナゾール、エタコナゾール、フェナリモール、フェンブコナゾール、フェンヘキサアミド、フェンプロピジン、フェンプロピモルフ、フルキンコナゾール、フルルプリルミドール、フルシラゾール、フルトリアホール、フルコナゾール、フルコナゾール−シス、ヘキサコナゾール、イマザリル、イマザリルサルフェート、イミベンコナゾール、イプコナゾール、メトコナゾール、ミクロブトアニル、ナフチフィン、ヌアリモール、オキスポコナゾール、パクロブトラゾール、ペフラゾエート、ペンコナゾール、ピペラリン、プロクロラズ、プロピコナゾール、プロチオコナゾール、ピリブチカルブ、ピリフェノキス、キンコナゾール、シメコナゾール、スピロキサミン、テブコナゾール、テルビナフィン、テトラコナゾール、トリアジメホン、トリアジメノール、トリデモルフ、トリフルミゾール、トリホリン、トリチコナゾール、ウニコナゾール、ウニコナゾール−P、ビニコナゾール、ボリコナゾール、1−(4−クロロフェニル)−2−(1H−1,2,4−トリアゾール−1−イル)シクロヘプタノール、メチル1−(2,2−ジメチル−2,3−ジヒドロ−1H−インデン−1−イル)−1H−イミダゾール−5−カルボキシレート、N’−{5−(ジフルオロメチル)−2−メチル−4−[3−(トリメチルシリル)プロポキシ]フェニル}−N−エチル−N−メチルイミドホルムアミド、N−エチル−N−メチル−N’−{2−メチル−5−(トリフルオロメチル)−4−[3−トリメチルシリル]プロポキシ}フェニル}−イミドホルムアミドおよびO−[1−(4−メトキシフェノキシ)−3,3−ジメチルブタン−2−イル]−1H−イミダゾール−1−カルボチオエート;
種、セレートフィルス種;
実施例1
2−[6−(4−フルオロ−2−ピリジン−3−イルチアゾール−5−イル)ピリジン−2−イル]ピリミジン
HPLC−MS:logP(HCOOH)=2.15、質量(m/z):336.1 (M+H)+、1H−NMR(D6−DMSO):7.60(m,2H)、8.00(d,1H)、8.15(t,1H)、8.35(d,1H)、8.40(d,1H)、8.75(d,1H)、9.05(m,2H)、9.20ppm(m,1H)。
2−{6−[4−クロロ−2−(ピリジン−3−イル)−1,3−チアゾール−5−イル]ピリジン−2−イル}ピリミジンおよび5−クロロ−2−{6−[4−クロロ−2−(ピリジン−3−イル)−1,3−チアゾール−5−イル]ピリジン−2−イル}ピリミジン
収率:52.2mg(理論の15%)
HPLC−MS:logP(HCOOH)=2.27、質量(m/z):352.0 (M+H)+、1H−NMR(D6−DMSO):7.38(t,1H)、7.42(m,1H)、8.02(t、1H)、8.31(m,1H)、8.41(d,1H)、8.47(d,1H)、8.70(m,1H)、8.97(d,2H)、9.24ppm(m,1H)。
収率:15mg(理論の4%)
HPLC−MS:logP(HCOOH)=3.27、質量(m/z):385.9、387.9(M+H)+、1H−NMR(D6−DMSO):7.44(m,1H)、8.02(t,1H)、8.33(m,1H)、8.41(d,1H)、8.43(d,1H)、8.71(m,1H)、8.91(s,2H)、9.24ppm(m,1H)。
1)logP値は、EEC Directive 79/831 Annex V.A8に従って逆相カラム(C18)を用いてHPLC(高性能液体クロマトグラフィー)により決定した。温度:55℃。
Myzus試験(噴霧処理)
溶媒:78重量部のアセトン
1.5重量部のジメチルホルムアミド
乳化剤: 0.5重量部のアルキルアリールポリグリコールエーテル
実施例番号1
Claims (5)
- 式(I):
G1は、N、CHまたはC−ハロゲンを表し、
G2は、
R1は、シアノ、ニトロまたはハロゲンを表し、および
G3は、ジオキサニル、オキサゾリニル、ジヒドロオキサジアジニル、ジヒドロジオキサジニルおよびヒドロキシピリジルからなる群からの置換ヘテロ環を表し、または
G3は、トリアゾリノニル、ジヒドロジオキサジニル、ジヒドロオキサジアジニル、ジオキソラニル、ジオキサニル(特に1,3−ジオキサン−2−イル)、ピペリジノニル、ピロリジノニルおよびピラゾリノニルからなる群からの必要に応じて置換されたヘテロシクリルにより、必要に応じて置換されたフェニルにより、必要に応じて置換されたヘテロアリールによりまたは必要に応じて置換されたヘテロアリールアルキルにより置換されたヘテロアリールを表す)
を表す〕
で示される化合物、および式(I)で示される化合物の塩および金属錯体。 - G3は、置換ヘテロ環を表す、請求項1に記載の式(I)で示される化合物。
- G3は、置換ヘテロアリールを表す、請求項1に記載の式(I)で示される化合物。
- 請求項1〜3のいずれかに記載の少なくとも1つの式(I)で示される化合物を含むことを特徴とする組成物。
- 請求項1〜3のいずれかに記載の式(I)で示される化合物または請求項4に記載の組成物を、害虫および/またはその生息地に作用させることを特徴とする、害虫を抑制するための方法。
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US8815271B2 (en) | 2010-11-03 | 2014-08-26 | Dow Agrosciences, Llc. | Pesticidal compositions and processes related thereto |
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- 2011-05-02 BR BR112012028280A patent/BR112012028280A2/pt not_active IP Right Cessation
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ES2494716T3 (es) | 2014-09-16 |
BR112012028280A2 (pt) | 2015-09-15 |
CN102971315B (zh) | 2015-07-22 |
CN102971315A (zh) | 2013-03-13 |
WO2011138285A1 (de) | 2011-11-10 |
EP2566865A1 (de) | 2013-03-13 |
JP2013525465A (ja) | 2013-06-20 |
EP2566865B1 (de) | 2014-06-25 |
US8686156B2 (en) | 2014-04-01 |
US20110319428A1 (en) | 2011-12-29 |
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