JP6889663B2 - 農薬の効用を有する分子ならびに関連する中間体、組成物及びプロセス - Google Patents
農薬の効用を有する分子ならびに関連する中間体、組成物及びプロセス Download PDFInfo
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- JP6889663B2 JP6889663B2 JP2017553380A JP2017553380A JP6889663B2 JP 6889663 B2 JP6889663 B2 JP 6889663B2 JP 2017553380 A JP2017553380 A JP 2017553380A JP 2017553380 A JP2017553380 A JP 2017553380A JP 6889663 B2 JP6889663 B2 JP 6889663B2
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- Prior art keywords
- alkyl
- haloalkyl
- group
- dichloro
- alkoxy
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- 239000000203 mixture Substances 0.000 title claims description 63
- 238000000034 method Methods 0.000 title claims description 54
- 239000000575 pesticide Substances 0.000 title claims description 22
- 230000008569 process Effects 0.000 title claims description 5
- 239000000543 intermediate Substances 0.000 title description 8
- -1 2,5-dioxoimidazolidinyl Chemical group 0.000 claims description 344
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 108
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 76
- 229910052739 hydrogen Inorganic materials 0.000 claims description 72
- 229910052801 chlorine Inorganic materials 0.000 claims description 61
- 229910052731 fluorine Inorganic materials 0.000 claims description 54
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 43
- 229910052794 bromium Inorganic materials 0.000 claims description 42
- 239000004480 active ingredient Substances 0.000 claims description 39
- PIGFYZPCRLYGLF-UHFFFAOYSA-N Aluminum nitride Chemical compound [Al]#N PIGFYZPCRLYGLF-UHFFFAOYSA-N 0.000 claims description 38
- 241000607479 Yersinia pestis Species 0.000 claims description 31
- 125000003545 alkoxy group Chemical group 0.000 claims description 29
- 229910052740 iodine Inorganic materials 0.000 claims description 25
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 24
- 239000002253 acid Substances 0.000 claims description 24
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims description 22
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 20
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 20
- 125000003507 tetrahydrothiofenyl group Chemical group 0.000 claims description 20
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims description 18
- 125000000262 haloalkenyl group Chemical group 0.000 claims description 18
- 125000001188 haloalkyl group Chemical group 0.000 claims description 18
- 125000006769 halocycloalkoxy group Chemical group 0.000 claims description 18
- 125000005347 halocycloalkyl group Chemical group 0.000 claims description 18
- 125000002053 thietanyl group Chemical group 0.000 claims description 17
- 125000002393 azetidinyl group Chemical group 0.000 claims description 14
- 125000003566 oxetanyl group Chemical group 0.000 claims description 14
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 claims description 14
- 229910052799 carbon Inorganic materials 0.000 claims description 13
- 125000001424 substituent group Chemical group 0.000 claims description 13
- 125000002757 morpholinyl group Chemical group 0.000 claims description 12
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 11
- 238000007792 addition Methods 0.000 claims description 9
- 229910052717 sulfur Inorganic materials 0.000 claims description 9
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 8
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 7
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 5
- JMTBNBFBHBCERV-UHFFFAOYSA-N 2-(thiolan-2-yloxy)thiolane Chemical compound C1CCSC1OC1SCCC1 JMTBNBFBHBCERV-UHFFFAOYSA-N 0.000 claims description 5
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 5
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 5
- 125000004193 piperazinyl group Chemical group 0.000 claims description 5
- 125000003386 piperidinyl group Chemical group 0.000 claims description 5
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 5
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 5
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 150000001204 N-oxides Chemical class 0.000 claims description 2
- 101150044039 PF12 gene Proteins 0.000 claims description 2
- 101100082996 Plasmodium falciparum (isolate 3D7) PF36 gene Proteins 0.000 claims description 2
- 125000004043 oxo group Chemical group O=* 0.000 claims description 2
- 239000012453 solvate Substances 0.000 claims description 2
- 239000013078 crystal Substances 0.000 claims 1
- 238000005481 NMR spectroscopy Methods 0.000 description 215
- 239000007787 solid Substances 0.000 description 183
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 171
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 150
- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 112
- 239000000243 solution Substances 0.000 description 102
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- 238000002360 preparation method Methods 0.000 description 61
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 57
- 239000011541 reaction mixture Substances 0.000 description 56
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- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 54
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- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 42
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- 239000006260 foam Substances 0.000 description 40
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 39
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 37
- 238000002844 melting Methods 0.000 description 36
- 230000008018 melting Effects 0.000 description 36
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- 239000003921 oil Substances 0.000 description 24
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- 241000894007 species Species 0.000 description 24
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 23
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 23
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 22
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 22
- 239000010409 thin film Substances 0.000 description 22
- 239000003480 eluent Substances 0.000 description 21
- 238000003756 stirring Methods 0.000 description 21
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 20
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 20
- 238000000746 purification Methods 0.000 description 19
- 229910052938 sodium sulfate Inorganic materials 0.000 description 19
- 235000011152 sodium sulphate Nutrition 0.000 description 19
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 18
- 150000001733 carboxylic acid esters Chemical class 0.000 description 18
- 239000012071 phase Substances 0.000 description 17
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 16
- 239000012267 brine Substances 0.000 description 16
- 239000012230 colorless oil Substances 0.000 description 16
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 16
- 235000019341 magnesium sulphate Nutrition 0.000 description 16
- 239000000047 product Substances 0.000 description 16
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 16
- 239000000126 substance Substances 0.000 description 16
- 238000011282 treatment Methods 0.000 description 16
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 238000011065 in-situ storage Methods 0.000 description 15
- LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide Substances CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 14
- 238000002451 electron ionisation mass spectrometry Methods 0.000 description 14
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 14
- 229920006395 saturated elastomer Polymers 0.000 description 14
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 13
- FPIRBHDGWMWJEP-UHFFFAOYSA-N 1-hydroxy-7-azabenzotriazole Chemical compound C1=CN=C2N(O)N=NC2=C1 FPIRBHDGWMWJEP-UHFFFAOYSA-N 0.000 description 12
- PAQZWJGSJMLPMG-UHFFFAOYSA-N 2,4,6-tripropyl-1,3,5,2$l^{5},4$l^{5},6$l^{5}-trioxatriphosphinane 2,4,6-trioxide Chemical compound CCCP1(=O)OP(=O)(CCC)OP(=O)(CCC)O1 PAQZWJGSJMLPMG-UHFFFAOYSA-N 0.000 description 12
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 12
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- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 9
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- 235000001892 vitamin D2 Nutrition 0.000 description 1
- 239000011653 vitamin D2 Substances 0.000 description 1
- 239000000664 voltage gated sodium channel blocking agent Substances 0.000 description 1
- 229960005080 warfarin Drugs 0.000 description 1
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- 229940048462 zinc phosphide Drugs 0.000 description 1
- AMHNZOICSMBGDH-UHFFFAOYSA-L zineb Chemical compound [Zn+2].[S-]C(=S)NCCNC([S-])=S AMHNZOICSMBGDH-UHFFFAOYSA-L 0.000 description 1
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Classifications
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- Chemical & Material Sciences (AREA)
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- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pyrrole Compounds (AREA)
- Pyridine Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Quinoline Compounds (AREA)
- Indole Compounds (AREA)
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Description
本出願は、全て2015年4月17日に出願された米国仮特許出願第62/148830号、同第62/148837号、同第62/148809号、同第62/148814号、同第62/148818号、及び同第62/148824号の利益ならびに優先権を主張するものである。上記に特定された出願の全ての内容全体が、本明細書によって参照により本出願に援用される。
CropLife America, The Cost of New Agrochemical Product Discovery, Development & Registration, and Research & Development predictions for the Future, 2010。
Drewes, M., Tietjen, K., Sparks, T.C., High-Throughput Screening in Agrochemical Research, Modern Methods in Crop Protection Research, Part I, Methods for the
Design and Optimization of New Active Ingredients, Jeschke, P., Kramer, W., Schirmer, U., and Matthias W.編, p. 1-20, 2012。
Gubler, D., Resurgent Vector-Borne Diseases as a Global Health Problem, Emerging Infectious Diseases, Vol. 4, No. 3, p. 442-450, 1998。
Korb, J., Termites, Current Biology, Vol. 17, No. 23, 2007。
Matthews, G., Integrated Vector Management: Controlling Vectors of Malaria and
Other Insect Vector Borne Diseases, Ch. 1, p. 1, 2011。
Nicol, J., Turner S., Coyne, L., den Nijs, L., Hocksland, L., Tahna-Maafi, Z.,
Current Nematode Threats to World Agriculture, Genomic and Molecular Genetics of Plant - Nematode Interactions, p. 21-43, 2011。
Pimental, D., Pest Control in World Agriculture, Agricultural Sciences - Vol. II, 2009。
Rivero, A., Vezilier, J., Weill, M., Read, A., Gandon, S., Insect Control of Vector-Borne Diseases: When is Insect Resistance a Problem? Public Library of Science Pathogens, Vol. 6, No. 8, p. 1-9, 2010。
Sparks T.C., Nauen R., IRAC: Mode of action classification and insecticide resistance management, Pesticide Biochemistry and Physiology(2014) 2014年12月4日にオンラインで利用可能。
Speiser, B., Molluscicides, Encyclopedia of Pest Management, Ch. 219, p. 506-508, 2002。
Whalon, M., Mota-Sanchez, D., Hollingworth, R., Analysis of Global Pesticide Resistance in Arthropods, Global Pesticide Resistance in Arthropods, Ch. 1, p. 5-33, 2008。
本定義において与えられる例は、概して非網羅的であり、本開示を限定するものと解釈されるべきではない。置換基は、それが結合する特定の分子に関する化学結合則と立体的適合性制限とに適合すべきであることが理解される。これらの定義は、ただ本開示の目的のために使用されるものである。
具体的な例としては、限定されないが、活性成分群アルファに列記される物質が挙げられる。
(1) (3-エトキシプロピル)水銀ブロミド、1,2-ジブロモエタン、1,2-ジクロロエタン、1,2-ジクロロプロパン、1,3-ジクロロプロペン、1-MCP、1-メチルシクロプロペン、1-ナフトール、2-(オクチルチオ)エタノール、2,3,3-TPA、2,3,5-トリヨード安息香酸、2,3,6-TBA、2,4,5-T、2,4,5-TB、2,4,5-TP、2,4-D、2,4-DB、2,4-DEB、2,4-DEP、2,4-DES、2,4-DP、2,4-MCPA、2,4-MCPB、2iP、2-メトキシエチル水銀クロリド、2-フェニルフェノール、3,4-DA、3,4-DB、3,4-DP、3,6-ジクロロピコリン酸、4-アミノピリジン、4-CPA、4-CPB、4-CPP、4-ヒドロキシフェネチルアルコール、8-ヒドロキシキノリンサルフェート、8-フェニル水銀オキシキノリン、アバメクチン(abamectin)、アバメクチン-アミノメチル、アブシジン酸、ACC、アセフェート、アセキノシル、アセタミプリド、アセチオン(acethion)、アセトクロル(acetochlor)、アセトフェナート(acetofenate)、アセトホス(acetophos)、アセトプロール(acetoprole)、アシベンゾラル(acibenzolar)、アシフルオルフェン、アクロニフェン(aclonifen)、ACN、アクレプ(acrep)、アクリナトリン(acrinathrin)、アクロレイン、アクリロニトリル、アシペタクス(acypetacs)、アフィドピロペン(afidopyropen)、アフォキソラネル(afoxolaner)、アラクロール(alachlor)、アラナップ(alanap)、アラニカルブ(alanycarb)、アルベンダゾール、アルジカルブ、アルジカルブスルホン、アルジモルフ(aldimorph)、アルドキシカルブ、アルドリン、アレトリン(allethrin)、アリシン、アリドクロル、アロサミジン、アロキシジム、アリルアルコール、アリキシカルブ、アロラック(alorac)、アルファ-シペルメトリン、アルファ-エンドスルファン、アルファメトリン(alphamethrin)、アルトレタミン、リン化アルミニウム(aluminium phosphide)、リン化アルミニウム(aluminum phosphide)、アメトクトラジン、アメトリジオン(ametridione)、アメトリン(ametryn)、アメトリン(ametryne)、アミブジン(amibuzin)、アミカルバゾン、アミカルチアゾル(amicarthiazol)、アミジチオン(amidithion)、アミドフルメト(amidoflumet)、アミドスルフロン(amidosulfuron)、アミノカルブ(aminocarb)、アミノシクロピラクロル(aminocyclopyrachlor)、アミノピラリド(aminopyralid)、アミノトリアゾール、アミプロホス-メチル(amiprofos-methyl)、アミプロホス(amiprophos)、アミプロホス-メチル(amiprophos-methyl)、アミスルブロム(amisulbrom)、アミトン(amiton)、アミトラツ(amitraz)、アミトロール、スルファミン酸アンモニウム、アンバム、アモルファスシリカゲル、アモルファス二酸化ケイ素、アムプロピルホス(ampropylfos)、AMS、アナバシン、アンシミドール(ancymidol)、アニラジン、アニロホス(anilofos)、アニスロン(anisuron)、アントラキノン、アンツ(antu)、アフォレート(apholate)、アラマイト、アルプロカルブ(arprocarb)、亜ヒ酸、アソメート(asomate)、アスピリン、アシュラム、アチダチオン(athidathion)、アトラトン(atraton)、アトラジン、アウレオフンジン(aureofungin)、アベルメクチンB1、AVG、アビグリシン(aviglycine)、アザコナゾール(azaconazole)、アザジラクチン(azadirachtin)、アザフェニジン(azafenidin)、アザメチホス(azamethiphos)、アジジチオン(azidithion)、アジムスルフロン(azimsulfuron)、アジンホスエチル、アジンホス-エチル、アジンホスメチル、アジンホス-メチル、アジプロトリン(aziprotryn)、アジプロトリン(aziprotryne)、アジチラム(azithiram)、アゾベンゼン、アゾシクロチン(azocyclotin)、アゾトエート(azothoate)、アゾキシストロビン、バクメデシュ(bachmedesh)、バルバン、バルバネート(barbanate)、ヘキサフルオロケイ酸バリウム、バリウムポリスルフィド、ケイフッ化バリウム、バルトリン、塩基性炭酸銅、塩基性塩化銅、塩基性硫酸銅、BCPC、ベフルブタミド、ベナラキシル、ベナラキシル-M、ベナゾリン、ベンカルバゾン、ベンクロチアズ(benclothiaz)、ベンダキングビングチ(bendaqingbingzhi)、ベンジオカルブ、ベンジオキシド(bendioxide)、ベネフィン(benefin)、
ベンフルラリン、ベンフラカルブ、ベンフレセート、ベンミフアンカオアン(benmihuangcaoan)、ベノダニル(benodanil)、ベノミル、ベノキサコール、ベノキサホス(benoxafos)、ベンキノックス(benquinox)、ベンスルフロン、ベンスリド、ベンスルタップ(bensultap)、ベンタルロン(bentaluron)、ベンタゾン(bentazon)、ベンタゾン(bentazone)、ベンチアバリカルブ、ベンチアゾール(benthiazole)、ベンチオカルブ、ベントラニル(bentranil)、ベンザドクス(benzadox)、ベンズアルコニウムクロリド(benzalkonium chloride)、ベンザマクリル(benzamacril)、ベンザミゾール(benzamizole)、ベンザモルフ(benzamorf)、ベンゼンヘキサクロリド、ベンズフェンジゾン(benzfendizone)、ベンズイミン(benzimine)、ベンジプラム(benzipram)、ベンゾビシクロン(benzobicyclon)、ベンゾエピン、ベンゾフェナプ(benzofenap)、ベンゾフルオル(benzofluor)、ベンゾヒドロキサム酸、ベンゾメート(benzomate)、ベンゾホスフェート(benzophosphate)、ベンゾチアジアゾール、ベンゾビンジフルピル、ベンゾキシメート(benzoximate)、ベンゾイルプロップ(benzoylprop)、ベンズチアズロン(benzthiazuron)、ベンズオカオトング(benzuocaotong)、安息香酸ベンジル、ベンジルアデニン、ベルベリン、ベータ-シフルトリン、ベータ-シペルメトリン、ベトキサジン(bethoxazin)、BHC、ビアラホス、ビシクロピロン、ビフェナゼート、ビフェノックス、ビフェントリン、ビフジュンチ(bifujunzhi)、ビラナホス(bilanafos)、ビナパクリル、ビングキングキシアオ(bingqingxiao)、ビオアレトリン(bioallethrin)、ビオエタノメトリン(bioethanomethrin)、ビオペルメトリン(biopermethrin)、ビオレスメトリン、ビフェニル、ビサジル(bisazir)、ビスメルチアゾール(bismerthiazol)、ビスメルチアゾール-銅、メチレンジ(x-ナフタレン-y-スルホネート)ビスフェニル水銀(bisphenylmercury methylenedi(x-naphthalene-y-sulphonate))、ビスピリバック(bispyribac)、ビストリフルロン(bistrifluron)、ビスルタップ(bisultap)、ビテルタノール(bitertanol)、ビチオノール、ビキサフェン、ブラスチシジン-S(blasticidin-S)、ボラックス(borax)、ボルドー液、ホウ酸、ボスカリド、BPPS、ブラシノリド(brassinolide)、ブラシノリド-エチル、ブレビコミン(brevicomin)、ブロディファコウム(brodifacoum)、ブロフェンプロックス(brofenprox)、ブロフェンバレレート(brofenvalerate)、ブロフラニリド(broflanilide)、ブロフルトリネート(brofluthrinate)、ブロマシル、ブロマジオロン(bromadiolone)、ブロムクロホス(bromchlophos)、ブロメタリン(bromethalin)、ブロメトリン(bromethrin)、ブロムフェンビンホス(bromfenvinfos)、ブロモアセトアミド、ブロモボニル(bromobonil)、ブロモブチド、ブロモシクレン(bromociclen)、ブロモシクレン(bromocyclen)、ブロモ-DDT、ブロモフェノキシム(bromofenoxim)、ブロモホス(bromofos)、ブロモメタン、ブロモホス(bromophos)、ブロモホス-エチル、ブロモプロピレート、ブロモタロニル(bromothalonil)、ブロモキシニル、ブロムピラゾン(brompyrazon)、ブロムコナゾール(bromuconazole)、ブロノポール、BRP、BTH、ブカルポラート(bucarpolate)、ブフェンカルブ(bufencarb)、ブミナホス(buminafos)、ブピリメート(bupirimate)、ブプロフェジン、ブルガンディ混合物、ブスルファン(busulfan)、ブスルファン(busulphan)、ブタカルブ(butacarb)、ブタクロール(butachlor)、ブタフェナシル(butafenacil)、ブタム(butam)、ブタミホス(butamifos)、ブタン-フィプロニル、ブタチオホス(butathiofos)、ブテナクロール(butenachlor)、ブテン-フィプロニル、ブテトリン(butethrin)、ブチダゾール(buthidazole)、ブチオベート(buthiobate)、ブチウロン(buthiuron)、ブチホス(butifos)、ブトカルボキシム(butocarboxim)、ブトネート(butonate)、ブトピロノキシル(butopyronoxyl)、ブトキシカルボキシム(butoxycarboxim)、ブトラリン(butralin)、ブトリゾール(butrizol)、ブトロキシジム(butroxydim)、ブツロン(buturon)、ブチルアミン、ブチレート、ブチルクロロホス(butylchlorophos)、ブチレン-フィプロニル、カコジル酸、カズサホス、カフェンストロール、カルシフェロール、ヒ酸カルシウム、塩素酸カルシウム、カルシウムシアナミド、シアン化カルシウム、カルシウムポリスルフィド(calcium polysulfide)、カルビンホス(calvinphos)、カムベンジクロル(cambendichlor)、カムフェクロル(camphechlor)、ショウノウ、
カプタホール(captafol)、カプタン(captan)、カーバム、カルバモルフ(carbamorph)、カルバノレート(carbanolate)、カルバリル(carbaril)、カルバリル(carbaryl)、カルバスラム(carbasulam)、カルバチオン(carbathion)、カルベンダジム、カルベンダゾール(carbendazol)、カルベタミド(carbetamide)、カルボフェノチオン(carbofenotion)、カルボフラン、二硫化炭素、四塩化炭素、硫化カルボニル、カルボフェノチオン、カルボホス(carbophos)、カルボスルファン、カルボキサゾール(carboxazole)、カルボキシド(carboxide)、カルボキシン、カルフェントラゾン、カルプロパミド、カルタップ、カルバクロール(carvacrol)、カルボン、CAVP、CDAA、CDEA、CDEC、セロシジン(cellocidin)、CEPC、セラルア(ceralure)、セレノックス(cerenox)、サバジラ(cevadilla)、チェシャント混合物(Cheshunt mixture)、キナルホス(chinalphos)、キナルホス-メチル、キノメチオナト(chinomethionat)、キノメチオネート(chinomethionate)、キララキシル(chiralaxyl)、キトサン、クロベンチアゾン(chlobenthiazone)、クロメトキシフェン(chlomethoxyfen)、クロラロース(chloralose)、クロラムベン(chloramben)、クロラミンホスホラス(chloramine phosphorus)、クロラムフェニコル(chloramphenicol)、クロラニホルメタン(chloraniformethan)、クロラニル、クロラノクリル(chloranocryl)、クロラントラニリプロール(chlorantraniliprole)、クロラジホップ(chlorazifop)、クロラジン(chlorazine)、クロルベンシド、クロルベンズロン(chlorbenzuron)、クロルビシクレン(chlorbicyclen)、クロルブロムロン(chlorbromuron)、クロルブファム(chlorbufam)、クロルデン(chlordane)、クロルデコン(chlordecone)、クロルジメフォルム(chlordimeform)、クロレンペントリン(chlorempenthrin)、クロルエタゼート(chloretazate)、クロルエセホン(chlorethephon)、クロレトキシホス(chlorethoxyfos)、クロレツロン(chloreturon)、クロルフェナク(chlorfenac)、クロルフェナピル、クロルフェナゾール(chlorfenazole)、クロルフェネトール(chlorfenethol)、クロルフェニジム(chlorfenidim)、クロルフェンプロップ(chlorfenprop)、クロルフェンソン(chlorfenson)、クロルフェンスルフィド(chlorfensulphide)、クロルフェンビンホス(chlorfenvinphos)、クロルフェンビンホス-メチル、クロルフルアズロン(chlorfluazuron)、クロルフルラゾール(chlorflurazole)、クロルフルレコール(chlorflurecol)、クロルフルレン(chlorfluren)、クロルフルレノール(chlorflurenol)、クロリダゾン、クロリムロン(chlorimuron)、クロリネート(chlorinate)、クロル-IPC、クロルメホス(chlormephos)、クロルメコート(chlormequat)、クロルメスロン(chlormesulone)、クロルメトキシニル(chlormethoxynil)、クロルニジン(chlornidine)、クロルニトロフェン(chlomitrofen)、クロロ酢酸、クロロベンジレート、クロロジニトロナフタレン類、クロロフェニゾ
ン(chlorofenizon)、クロロホルム、クロロメブホルム(chloromebuform)、クロロメチウロン(chloromethiuron)、クロロネブ(chloroneb)、クロロファシノン(chlorophacinone)、クロロホス(chlorophos)、クロロピクリン、クロロポン(chloropon)、クロロプロピレート(chloropropylate)、クロロタロニル、クロロトルロン、クロロキシフェニジム(chloroxifenidim)、クロロクスロン(chloroxuron)、クロロキシニル(chloroxynil)、クロルホニウム(chlorphonium)、クロルホキシム(chlorphoxim)、クロルプラゾホス(chlorprazophos)、クロルプロカルブ(chlorprocarb)、クロルプロファム、クロルピリホス(chlorpyrifos)、クロルピリホス-メチル、クロルキノクス(chlorquinox)、クロルスルフロン(chlorsulfuron)、クロルタル(chlorthal)、クロルチアミド、クロルチオホス(chlorthiophos)、クロルトルロン(chlortoluron)、クロゾリネート(chlozolinate)、クルトサン(chltosan)、コレカルシフェロール、コリンクロリド、クロマフェノジド(chromafenozide)、シクロヘキシミド(cicloheximide)、シメクタカルブ(cimectacarb)、シメタカルブ(cimetacarb)、シネリンI、シネリンII、シネリン類(cinerines)、シニドン-エチル(cinidon-ethyl)、シンメチリン(cinmethylin)、シノスルフロン(cinosulfuron)、シントフェン(cintofen)、シオブチド(ciobutide)、シサニリド(cisanilide)、シスメトリン(cismethrin)、クラシホス(clacyfos)、クレホキシジム(clefoxydim)、クレンピリン(clenpirin)、クレンピリン(clenpyrin)、クレトジム(clethodim)、クリムバゾール(climbazole)、クリオジネート(cliodinate)、クロジナホップ(clodinafop)、クロエトカルブ(cloethocarb)、クロフェンセト(clofencet)、クロフェノタン(clofenotane)、クロフェンテジン(clofentezine)、クロフェンビンホス(clofenvinfos)、クロフィブリン酸(clofibric acid)、クロフォプ(clofop)、クロマゾン(clomazone)、クロメプロップ(clomeprop)、クロニトラリド(clonitralid)、クロプロップ(cloprop)、クロプロキシジム(cloproxydim)、クロピラリド、クロキントセット(cloquintocet)、クロランスラム(cloransulam)、クロサンテル(closantel)、クロチアニジン、クロトリマゾール、クロキシホナック(cloxyfonac)、クロキシラコン(cloxylacon)、クロジラコン(clozylacon)、CMA、CMMP、CMP、CMU,コドレルア(codlelure)、コレカルシフェロール(colecalciferol)、コロホネート(colophonate)、銅8-キノリノレート(copper 8-quinolinolate)、酢酸銅、酢酸亜ヒ酸銅、ヒ酸銅、炭酸銅(塩基性)、水酸化銅、ナフテン酸銅、オレイン酸銅、オキシ塩化銅、ケイ酸銅、硫酸銅、硫酸銅(塩基性)、クロム酸亜鉛銅、クマクロル(coumachlor)、クマフェン(coumafene)、クマホス(coumafos)、クマフリル(coumafuryl)、クマホス(coumaphos)、クマテトラリル、クメトキシストロビン(coumethoxystrobin)、クミトエート(coumithoate)、クモキシストロビン(coumoxystrobin)、CPMC、CPMF、CPPC、クレダジン(credazine)、クレゾール、クレゾール酸、クリミジン(crimidine)、クロタミトン(crotamiton)、クロトキシホス(crotoxyfos )、クロトキシホス(crotoxyphos)、クルホメート(crufomate)、氷晶石、キュウルア(cue-lure)、クフラネブ(cufraneb)、クミレロン(cumyleron)、クミルロン(cumyluron)、クプロバム(cuprobam)、酸化第一銅、クルクメノール(curcumenol)、CVMP、シアナミド、シアナトリン(cyanatryn)、シアナジン(cyanazine)、シアノフェンホス(cyanofenphos)、シアン、シアノホス(cyanophos)、シアントエート(cyanthoate)、シアントラニリプロール(cyantraniliprole)、シアヌル酸、シアゾファミド(cyazofamid)、シブトリン(cybutryne)、シクラフラミド(cyclafuramid)、シクラニリド(cyclanilide)、シクラニリプロール(cyclaniliprole)、シクレトリン(cyclethrin)、シクロエート(cycloate)、シクロヘキシミド、シクロプレート(cycloprate)、シクロプロトリン(cycloprothrin)、シクロピリモレート(cyclopyrimorate)、シクロスルファムロン(cyclosulfamuron)、シクロキシジム(cycloxydim)、シクルロン(cycluron)、シエノピラフェン(cyenopyrafen)、シフルフェナミド(cyflufenamid)、シフルメトフェン(cyflumetofen)、シフルトリン(cyfluthrin)、シハロホップ(cyhalofop)、シハロトリン(cyhalothrin)、シヘキサチン(cyhexatin)、シミアゾール(cymiazole)、シモキサニル(cymoxanil)、シオメトリニル(cyometrinil)、シペンダゾール(cypendazole)、シペルメトリン(cypermethrin)、シペルコート(cyperquat)、シフェノトリン(cyphenothrin)、シプラジン(cyprazine)、シプラゾール(cyprazole)、シプロコナゾール(cyproconazole)、シプロジニル(cyprodinil)、シプロフラム(cyprofuram)、シプロミド(cypromid)、シプロスルファミド(cyprosulfamide)、シロマジン(cyromazine)、シチオエート(cythioate)、シトレックス(cytrex)、ダイムロン、ダラポン、ダミノジッド(daminozide)、ダイオウトング(dayoutong)、ダゾメット(dazomet)、DBCP、d-ショウノウ、DCB、DCIP、DCPA、DCPTA、DCU、DDD、DDPP、DDT、DDVP、デバカルブ(debacarb)、デカフェンチン(decafentin)、デカメトリン(decamethrin)、デカルボフラン(decarbofuran)、ディート、デヒドロ酢酸、ジクワット(deiquat)、デラクロール(delachlor)、デルナブ(delnav)、デルタメトリン(deltamethrin)、デメフィオン(demephion)、デメフィオン-O、デメフィオン-S、デメトン、デメトン-メチル、デメトン-O、デメトン-O-メチル、デメトン-S、デメトン-S-メチル、デメトン-S-メチルスルホン(demeton-S-methyl sulphone)、デメトン-S-メチルスルホン(demeton-S-methylsulphon)、DEP、デパレトリン(depallethrine)、デリス、デスメジファム(desmedipham)、デスメトリン(desmetryn)、デスメトリン(desmetryne)、d-ファンシルクエビンギュチ(d-fanshiluquebingjuzhi)、ジアフェンチウロン(diafenthiuron)、ジアリホル(dialifor)、ジアリホス(dialifos)、ジアレート(diallate)、ジアミダホス(diamidafos)、ジアナット(dianat)、珪藻土、珪藻岩、ダイアジノン(diazinon)、ジブロム(dibrom)、フタル酸ジブチル、コハク酸ジブチル、ジカンバ(dicamba)、ジカプトン(dicapthon)、ジクロベニル(dichlobenil)、ジクロフェンチオン(dichlofenthion)、ジクロフルアニド(dichlofluanid)、ジクロン(dichlone)、ジクロラルウレア(dichloralurea)、ジクロルベンズロン(dichlorbenzuron)、ジクロルフェニジム(dichlorfenidim)、ジクロルフルレコール(dichlorflurecol)、ジクロルフルレノール(dichlorflurenol)、ジクロルメート(dichlormate)、ジクロルミド(dichlormid)、ジクロロメタン、ジクロロメゾチアズ(dicloromezotiaz)、ジクロロフェン(dichlorophen)、ジクロルプロップ(dichlorprop)、ジクロルプロップ-P、ジクロルボス、ジクロゾリン(dichlozolin)、ジクロゾリン(dichlozoline)、ジクロブトラゾル(diclobutrazol)、ジクロシメット(diclocymet)、ジクロホプ(diclofop)、ジクロメジン(diclomezine)、ジクロラン(dicloran)、ジクロスラム(diclosulam)、ジコホル(dicofol)、ジコファン(dicophane)、ジクマロール(dicoumarol)、ジクレシル(dicresyl)、ジクロトホス、ジクリル(dicryl)、ジクマロール(dicumarol)、ジシクラニル(dicyclanil)、ジシクロノン(dicyclonon)、ジエルドリン(dieldrin)、ジエノクロル(dienochlor)、ジエタムコート(diethamquat)、ジエタチル(diethatyl)、ジエチオン(diethion)、ジエチオン(diethion)、ジエトフェンカルブ(diethofencarb)、ジエトレート(dietholate)、ジエトン(diethon)、ピロ炭酸ジエチル、ジエチルトルアミド、ジフェナクム(difenacoum)、ジフェノコナゾール(difenoconazole)、ジフェノペンテン(difenopenten)、ジフェノクスロン(difenoxuron)、ジフェンゾコート(difenzoquat)、ジフェチアロン(difethialone)、ジフロビダジン(diflovidazin)、ジフルベンズロン(diflubenzuron)、ジフルフェニカン(diflufenican)、ジフルフェニカニル(diflufenicanil)、ジフルフェンゾピル(diflufenzopyr)、ジフルメトリム(diflumetorim)、ジケグラック(dikegulac)、ジロル(dilor)、ジマチフ(dimatif)、ジメフルトリン(dimefluthrin)、ジメフォクス(dimefox)、ジメフロン(dimefuron)、ジメヒポ(dimehypo)、ジメピペレート(dimepiperate)、ジメタクロン(dimetachlone)、ジメタン(dimetan)、ジメタカルブ(dimethacarb)、ジメタクロン(dimethachlone)、ジメタクロル(dimethachlor)、ジメタメトリン(dimethametryn)、ジメテナミド(dimethenamid)、ジメテナミド-P、ジメチピン(dimethipin)、ジメチリモール(dimethirimol)、ジメトエート(dimethoate)、ジメトモルフ(dimethomorph)、ジメトリン(dimethrin)、ジメチルカルバート(dimethyl carbate)、ジメチルジスルフィド、フタル酸ジメチル、ジメチルビンホス(dimethylvinphos)、ジメチラン(dimetilan)、ジメキサノ(dimexano)、ジミダゾン(dimidazon)、ジモキシストロビン(dimoxystrobin)、ジムピラート(dimpylate)、ダイムロン(dimuron)、ジネックス(dinex)、ジンギュネズオ(dingjunezuo)、ジニコナゾール(diniconazole)、ジニコナゾール-M、ジニトラミン(dinitramine)、ジニトロフェノール類(dinitrophenols)、ジノブトン(dinobuton)、ジノカップ(dinocap)、ジノカップ-4、ジノカップ-6、ジノクトン(dinocton)、ジノフェネート(dinofenate)、ジノペントン(dinopenton)、ジノプロップ(dinoprop)、ジノサム(dinosam)、ジノセブ(dinoseb)、ジノスルホン(dinosulfon)、ジノテフラン(dinotefuran)、ジノテルブ(dinoterb)、ジノテルボン(dinoterbon)、ジオフェノラン(diofenolan)、ジオキサベンゾホス(dioxabenzofos)、ジオキサカルブ(dioxacarb)、ジオキサチオン(dioxathion)、ジオキサチオン(dioxation)、ジファシン(diphacin)、ジファシノン(diphacinone)、ジフェナジオン(diphenadione)、ジフェナミド(diphenamid)、ジフェナミド(diphenamide)、ジフェニルスルホン、ジフェニルアミン、ジフェニルスルフィド、ジプログル酸(diprogulic acid)、ジプロパリン(dipropalin)、ジプロペトリン(dipropetryn)、ジプテレックス(dipterex)、ジピメチトロン(dipymetitrone)、ジピリチオン(dipyrithione)、ジクワット(diquat)、四ホウ酸二ナトリウム、ジソスルタップ(disosultap)、ジスパルア(di
sparlure)、ジスグラン(disugran)、ジスル(disul)、ジスルフィラム、ジスルホトン(disulfoton)、ジタリムホス(ditalimfos)、ジチアノン(dithianon)、ジチクロホス(dithicrofos)、ジチオエーテル(dithioether)、ジチオメトン(dithiometon)、ジチオピル(dithiopyr)、ジウロン(diuron)、ジキサントゲン(dixanthogen)、d-リモネン、DMDS、DMPA、DNOC、ドデモルフ(dodemorph)、ドジシン(dodicin)、ドジン(dodine)、ドフェナピン(dofenapyn)、ドグアジン(doguadine)、ドミニカルア(dominicalure)、ドラメクチン(doramectin)、DPC、ドラゾキソロン(drazoxolon)、DSMA、d-トランス-アレトリン、d-トランス-レスメトリン、ズフリン(dufulin)、ダイムロン(dymron)、EBEP、EBP、エブホス(ebufos)、エクジステロン(ecdysterone)、エクロメゾール(echlomezol)、EDB、EDC、EDDP、エジフェンホス(edifenphos)、エグリナジン(eglinazine)、エマメクチン(emamectin)、EMPC、エンペントリン(empenthrin)、エナデニン(enadenine)、エンドスルファン、エンドタール(endothal)、エンドタール(endothall)、エンドチオン(endothion)、エンドリン、エネストロブリン(enestroburin)、エニルコナゾール(enilconazole)、エノキサストロビン(enoxastrobin)、エフィルスルホネート(ephirsulfonate)、EPN、エポコレオン(epocholeone)、エポフェノナン(epofenonane)、エポキシコナゾール(epoxiconazole)、エプリノメクチン(eprinomectin)、エプロナズ(epronaz)、EPTC、エルボン(erbon)、エルゴカルシフェロール、エルルジキシアンカオアン(erlujixiancaoan)、エスデパレトリン(esdepallethrine)、エスフェンバレレート(esfenvalerate)、ESP、エスプロカルブ(esprocarb)、エタセラシル(etacelasil)、エタコナゾール(etaconazole)、エタホス(etaphos)、エテム(etem)、エタボキサム(ethaboxam)、エタクロル(ethachlor)、エタルフルラリン(ethalfluralin)、エタメツルフロン(ethametsulfuron)、エタプロクロル(ethaprochlor)、エテフォン(ethephon)、エチジムロン(ethidimuron)、エチオフェンカルブ(ethiofencarb)、エチオレート(ethiolate)、エチオン、エチオジン(ethiozin)、エチプロール(ethiprole)、エチリモール(ethirimol)、エトエート-メチル(ethoate-methyl)、エトベンザニド(ethobenzanid)、エトフメセート(ethofumesate)、エトヘキサジオール(ethohexadiol)、エトプロップ(ethoprop)、エトプロホス(ethoprophos)、エトキシフェン(ethoxyfen)、エトキシキン(ethoxyquin)、エトキシスルフロン(ethoxysulfuron)、エチクロゼート(ethychlozate)、ギ酸エチル、ピロリン酸エチル、エチラン(ethylan)、エチル-DDD、エチレン、エチレンジブロミド、エチレンジクロリド、エチレンオキシド、エチリシン(ethylicin)、エチル水銀2,3-ジヒドロキシプロピルメルカプチド、エチル水銀アセテート、エチル水銀ブロミド、エチル水銀クロリド、エチル水銀ホスフェート、エチノフェン(etinofen)、ETM、エトニプロミド(etnipromid)、エトベンザニド(etobenzanid)、エトフェンプロックス(etofenprox)、エトキサゾール(etoxazole)、エトリジアゾール(etridiazole)、エトリムホス(etrimfos)、エトリムホス(etrimphos)、オイゲノール、EXD、ファモキサドン(famoxadone)、ファムフル(famphur)、フェナック(fenac)、フェナミドン(fenamidone)、フェナミノスルフ(fenaminosulf)、フェナミンストロビン(fenaminstrobin)、フェナミホス(fenamiphos)、フェナパニル(fenapanil)、フェナリモル(fenarimol)、フェナスラム(fenasulam)、フェナザフロル(fenazaflor)、フェナザキン(fenazaquin)、フェンブコナゾール(fenbuconazole)、フェンブタチンオキシド(fenbutatin oxide)、フェンクロラゾール(fenchlorazole)、フェンクロルホス(fenchlorphos)、フェンクロホス(fenclofos)、フェンクロリム(fenclorim)、フェネタカルブ(fenethacarb)、フェンフルトリン(fenfluthrin)、フェンフラム(fenfuram)、フェンヘキサミド(fenhexamid)、フェニジン(fenidin)、フェニトロパン(fenitropan)、フェニトロチオン、フェニゾン(fenizon)、フェンジュントング(fenjuntong)、フェノブカルブ(fenobucarb)、フェノロボ(fenolovo)、フェノプロップ(fenoprop )、フェノチオカルブ(fenothiocarb)、フェノキサクリム(fenoxacrim)、フェノキサニル(fenoxanil)、フェノキサプロップ(fenoxaprop)、フェノキサプロップ-P、フェノキサスルフォン(fenoxasulfone)、フェノキシカルブ(fenoxycarb)、フェンピクロニル(fenpiclonil)、フェンピリトリン(fenpirithrin)、フェンプロパトリン(fenpropathrin)、フェンプロピジン(fenpropidin)、フェンプロピモルフ(fenpropimorph)、フェンピラザミン(fenpyrazamine)、フェンピロキシメート(fenpyroximate)、フェンキノトリオン(fenquinotrione)、フェンリダゾン(fenridazon)、フェンソン(fenson)、フェンスルフォチオン(fensulfothion)、フェンテラコール(fenteracol)、フェンチアプロップ(fenthiaprop)、フェンチオン、フェンチオン-エチル、フェンチアプロップ(fentiaprop)、フェンチン(fentin)、フェントラザミド(fentrazamide)、フェントリファニル(fentrifanil)、フェヌロン(fenuron)、フェヌロン-TCA、フェンバレレート(fenvalerate)、フェルバム(ferbam)、フェリムゾン(ferimzone)、リン酸第二鉄、硫酸第一鉄、フィプロニル、フラムプロップ(flamprop)、フラムプロプ-M、フラザスルフロン(flazasulfuron)、フロクマフェン(flocoumafen)、フロメトキン(flometoquin)、フロニカミド(flonicamid)、フロラスラム(florasulam)、フルアクリピリム(fluacrypyrim)、フルアジホップ(fluazifop)、フルアジホップ-P、フルアジナム(fluazinam)、フルアゾレート(fluazolate)、フルアズロン(fluazuron)、フルベンジアミド(flubendiamide)、フルベンジミン(flubenzimine)、フルブロシトリネート(flubrocythrinate)、フルカルバゾン(flucarbazone)、フルセトスルフロン(flucetosulfuron)、フルクロラリン(fluchloralin)、フルコフロン(flucofuron)、フルシクロクスロン(flucycloxuron)、フルシトリネート(flucythrinate)、フルジオキソニル(fludioxonil)、フルエネチル(fluenethyl)、フルエネチル(fluenetil)、フルエンスルホン(fluensulfone)、フルフェナセット(flufenacet)、フルフェネリム(flufenerim)、フルフェニカン(flufenican)、フルフェノクスロン(flufenoxuron)、フルフェノキシストロビン(flufenoxystrobin)、フルフェンプロックス(flufenprox)、フルフェンピル(flufenpyr)、フルフェンジン(flufenzine)、フルフィプロール(flufiprole)、フルヘキサフォン(fluhexafon)、フルメトリン(flumethrin)、フルメトベル(flumetover)、フルメトラリン(flumetralin)、フルメツラム(flumetsulam)、フルメジン(flumezin)、フルミクロラック(flumiclorac)、フルミオキサジン(flumioxazin)、フルミプロピン(flumipropyn)、フルモルフ(flumorph)、フルオメツロン(fluometuron)、フルオピコリド(fluopicolide)、フルオピラム(fluopyram)、フルオルベンシド(fluorbenside)、フルオリダミド(fluoridamid)、フルオロアセトアミド、フルオロ酢酸、フルオロクロリドン(fluorochloridone)、フルオロジフェン(fluorodifen)、フルオログリコフェン(fluoroglycofen)、フルオロイミド、フルオロミド(fluoromide)、フルオロミジン(fluoromidine)、フルオロニトロフェン(fluoronitrofen)、フルロキシピル(fluoroxypyr)、フルオチウロン(fluothiuron)、フルオトリマゾール(fluotrimazole)、フルオキサストロビン(fluoxastrobin)、フルポキサム(flupoxam)、フルプロパシル(flupropacil)、フルプロパジン(flupropadine)、フルプロパネート(flupropanate)、フルピラジフロン(flupyradifurone)、フルピルスルフロン(flupyrsulfuron)、フルキンコナゾール(fluquinconazole)、フルララネル(fluralaner)、フルラゾール(flurazole)、フルレコール(flurecol)、フルレノール(flurenol)、フルリドン(fluridone)、フルロクロリドン(flurochloridone)、フルロミジン(fluromidine)、フルロキシピル(fluroxypyr)、フルルプリミドル(flurprimidol)、フルルスラミド(flursulamid)、フルルタモン(flurtamone)、フルシラゾール(flusilazole)、フルスルファミド(flusulfamide)、フルテンジン(flutenzine)、フルチアセット(fluthiacet)、フルチアミド(fluthiamide)、フルチアニル(flutianil)、フルトラニル(flutolanil)、フルトリアホール(flutriafol)、フルバリネート(fluvalinate)、フルキサピロキサド(fluxapyroxad)、フルキソフェニム(fluxofenim)、ホルペル(folpel)、ホルペット(folpet)、ホメサフェン(fomesafen)、ホノホス(fonofos)、ホラムスルフロン(foramsulfuron)、ホルクロルフェヌロン(forchlorfenuron)、ホルムアルデヒド、ホルメタネート(formetanate)、ホルモチオン(formothion)、ホルムパラネート(formparanate)、ホサミン(fosamine)、ホセチル(fosetyl)、ホスメチラン(fosmethilan)、ホスピレート(fospirate)、ホスチアゼート(fosthiazate)、ホスチエタン(fosthietan)、フロンタリン(frontalin)、フサライド(fthalide)、フベリダゾール(fuberidazole)、フカオジング(fucaojing)、フカオミ(fucaomi)、フジュンマンチ(fujunmanzhi)、フルミ(fulumi)、フマリン(fumarin)、フナイヘカオリング(funaihecaoling)、フフェンチオウレア(fuphenthiourea)、フララン(furalane)、フララキシル(furalaxyl)、フラメトリン(furamethrin)、フラメトピル(furametpyr)、フランテブフェノジド(furan tebufenozide)、フラチオカルブ(furathiocarb)、フルカルバニル(furcarbanil)、フルコナゾール(furconazole)、フルコナゾール-シス、フレトリン(furethrin)、フルフラール、フリラゾール(furilazole)、フルメシクロックス(furmecyclox)、フロファネート(furophanate)、フリルオキシフェン(furyloxyfen)、ガンマ-BHC、ガンマ-シハロトリン(cyhalothrin)、ガンマ-HCH、ゲニット(genit)、ジベレリン酸、ジベレリンA3、ジベレリン類、グリフトル(gliftor)、グリトール(glitor)、グルコクロラロース(glucochloralose)、グルホシネート(glufosinate)、グルホシネート-P、グリオジン(glyodin)、グリオキシム(glyoxime)、グリホサート(glyphosate)、グリホシン(glyphosine)、ゴシプルア(gossyplure)、グランドルア(grandlure)、グリセオフルビン、グアノクチン(guanoctine)、グアザチン(guazatine)、ハラクリネート(halacrinate)、ハラウキシフェン(halauxifen)、ハルフェンプロックス(halfenprox)、ハロフェノジド(halofenozide)、ハロサフェン(halosafen)、ハロスルフロン(halosulfuron)、ハロキシジン(haloxydine)、ハロキシホップ(haloxyfop)、ハロキシホップ-P、ハロキシホップ-R、HCA、HCB、HCH、ヘメル(hemel)、ヘムパ(hempa)、HEOD、ヘプタクロル、ヘプタフルトリン(heptafluthrin)、ヘプテノホス(heptenophos)、ヘプトパルギル(heptopargil)、ハービマイシン(herbimycin)、ハービマイシンA、ヘテロホス(heterophos)、ヘキサクロル(hexachlor)、ヘキサクロラン(hexachloran)、ヘキサクロロアセトン、ヘキサクロロベンゼン、ヘキサクロロブタジエン、ヘキサクロロフェン、ヘキサコナゾール(hexaconazole)、ヘキサフルムロン(hexaflumuron)、ヘキサフルオラミン(hexafluoramin)、ヘキサフルレート(hexaflurate)、ヘキサルア(hexalure)、ヘキサミド(hexamide)、ヘキサジノン(hexazinone)、ヘキシルチオホス(hexylthiofos)、ヘキシチアゾクス(hexythiazox)、HHDN、ホロスルフ(holosulf)、ホモブラシノライド(homobrassinolid
e)、フアンカイウォ(huancaiwo)、フアンチョングジング(huanchongjing)、フアングカオリング(huangcaoling)、フアンジュンツオ(huanjunzuo)、ヒドラメチルノン(hydramethylnon)、ヒドラルガフェン(hydrargaphen)、消石灰、水素シアナミド(hydrogen cyanamide)、シアン化水素、ヒドロプレン(hydroprene)、ヒドロキシイソキサゾール(hydroxyisoxazole)、ヒメキサゾール(hymexazol)、ヒキンカルブ(hyquincarb)、IAA、IBA、IBP、イカリジン(icaridin)、イマザリル(imazalil)、イマザメタベンズ(imazamethabenz)、イマザモックス(imazamox)、イマザピク(imazapic)、イマザピル(imazapyr)、イマザキン(imazaquin)、イマゼタピル(imazethapyr)、イマゾスルフロン(imazosulfuron)、イミベンコナゾール(imibenconazole)、イミシアホス(imicyafos)、イミダクロプリド(imidacloprid)、イミダクロチズ(imidaclothiz)、イミノクタジン(iminoctadine)、イミプロトリン(imiprothrin)、イナベンフィド(inabenfide)、インダノファン(indanofan)、インダジフラム(indaziflam)、インドキサカルブ(indoxacarb)、イネジン(inezin)、滴虫土、ヨードボニル(iodobonil)、ヨードカルブ(iodocarb)、ヨードフェンホス(iodofenphos)、ヨードメタン、ヨードスルフロン(iodosulfuron)、イオフェンスルフロン(iofensulfuron)、イオキシニル(ioxynil)、イパジン(ipazine)、IPC、イプコナゾール(ipconazole)、イプフェンカルバゾン(ipfencarbazone)、イプロベンホス(iprobenfos)、イプロジオン(iprodione)、イプロバリカルブ(iprovalicarb)、イプリミダム(iprymidam)、イプスジエノール(ipsdienol)、イプセノール(ipsenol)、IPSP、IPX、イサミドホス(isamidofos)、イサゾホス(isazofos)、イソベンザン(isobenzan)、イソカルバミド(isocarbamid)、イソカルバミド(isocarbamide)、イソカルボホス(isocarbophos)、イソシル(isocil)、イソドリン(isodrin)、イソフェンホス(isofenphos)、イソフェンホス-メチル、イソフェタミド(isofetamid)、イソラン(isolan)、イソメチオジン(isomethiozin)、イソノルロン(isonoruron)、イソパムホス(isopamphos)、イソポリネート(isopolinate)、イソプロカルブ(isoprocarb)、イソプロシル(isoprocil)、イソプロパリン(isopropalin)、イソプロパゾール(isopropazol)、イソプロチオラン(isoprothiolane)、イソプロツロン(isoproturon)、イソピラザム(isopyrazam)、イソピリモール(isopyrimol)、イソチオエート(isothioate)、イソチアニル(isotianil)、イソウロン(isouron)、イソバレジオン(isovaledione)、イソキサベン(isoxaben)、イソキサクロルトール(isoxachlortole)、イソキサジフェン(isoxadifen)、イソキサフルトール(isoxaflutole)、イソキサピリホップ(isoxapyrifop)、イソキサチオン(isoxathion)、イスロン(isuron)、イベルメクチン、イクソキサベン(ixoxaben)、イゾパムホス(izopamfos)、イゾパムホス(izopamphos)、ジャポニルア(japonilure)、ジャポトリンス(japothrins)、ジャスモリン(jasmolin)I、ジャスモリンII、ジャスモン酸、ジアフアングコングゾング(jiahuangchongzong)、ジアジゼングクシアオリン(jiajizengxiaolin)、ジアクシアングジュンチ(jiaxiangjunzhi)、ジエカオワン(jiecaowan)、ジエカオキシ(jiecaoxi)、ジンガンマイシンA(jinganmycin A)、ヨードフェンホス(jodfenphos)、幼若ホルモンI、幼若ホルモンII、幼若ホルモンIII、カデトリン(kadethrin)、カッパ-ビフェントリン(kappa-bifenthrin)、カッパ-テフルトリン(kappa-tefluthrin)、カルブチレート(karbutilate)、カレタザン(karetazan)、カスガマイシン、ケジュンリン(kejunlin)、ケレバン(kelevan)、ケトスピラドックス(ketospiradox)、珪藻土、キネチン(kinetin)、キノプレン(kinoprene)、キララキシル(kiralaxyl)、クレソキシム-メチル(kresoxim-methyl)、クイカオキシ(kuicaoxi)、ラクトフェン(lactofen)、ラムダ-シハロトリン(cyhalothrin)、ラチルア(latilure)、ヒ酸鉛、レナシル、レピメクチン(lepimectin)、レプトホス(leptophos)、リアンベンジングチ(lianbenjingzhi)、石灰硫黄合剤、リンデン(lindane)、リネアチン(lineatin)、リニュロン(linuron)、リリムホス(lirimfos)、リトルア(litlure)、ループルア(looplure)、ルフェヌロン(lufenuron)、ルキシアンカオリン(luxiancaolin)、ルブジングジュンチ(lvdingjunzhi)、ルブフミジブチ(lvfumijvzhi)、ルブキシアンカオリン(lvxiancaolin)、リチダチオン(lythidathion)、M-74、M-81、MAA、リン化マグネシウム、マラチオン(malathion)、マルジソン(maldison)、マレイン酸ヒドラジド、マロノベン(malonoben)、マルトデキストリン、MAMA、マンカッパー(mancopper)、マンコゼブ(mancozeb)、マンデストロビン(mandestrobin)、マンジプロパミド(mandipropamid)、マネブ(maneb)、マトリン(matrine)、マジドックス(mazidox)、MCC、MCP、MCPA、MCPA-チオエチル、MCPB、MCPP、メベニル(mebenil)、メカルバム(mecarbam)、メカルビンジド(mecarbinzid)、メカルホン(mecarphon)、メコプロップ(mecoprop)、メコプロップ-P、メジメフォルム(medimeform)、メジノテルブ(medinoterb)、メドルア(medlure)、メフェナセット(mefenacet)、メフェノキサム(mefenoxam)、メフェンピル(mefenpyr)、メフルイジド(mefluidide)、メガトモ酸(megatomoic acid)、メリシルアルコール、メリトキシン(melitoxin)、MEMC、メナゾン、MEP、メパニピリム(mepanipyrim)、メペルフルトリン(meperfluthrin)、メフェネート(mephenate)、メホスホラン(mephosfolan)、メピコート(mepiquat)、メプロニル(mepronil)、メプチルジノカップ(meptyldinocap)、メルカプトジメツル(mercaptodimethur)、メルカプトホス(mercaptophos)、メルカプトホスチオール(mercaptophos thiol)、メルカプトチオン(mercaptothion)、塩化第二水銀、酸化第二水銀、塩化第一水銀、メルホス(merphos)、メルホスオキシド(merphos oxide)、メソプラジン(mesoprazine)、メソスルフロン(mesosulfuron)、メソトリオン(mesotrione)、メスルフェン(mesulfen)、メスルフェンホス(mesulfenfos)、メスルフェン(mesulphen)、メタクレゾール、メタフルミゾン(metaflumizone)、メタラキシル(metalaxyl)、メタラキシル-M、メタアルデヒド、メタム(metam)、メタミホップ(metamifop)、メタミトロン(metamitron)、メタホス(metaphos)、メタキソン(metaxon)、メタザクロル(metazachlor)、メタゾスルフロン(metazosulfuron)、メタゾキソロン(metazoxolon)、メトコナゾール(metconazole)、メテパ(metepa)、メトフルラゾン(metflurazon)、メタベンズチアズロン(methabenzthiazuron)、メタクリホス(methacrifos)、メタルプロパリン(methalpropalin)、メタム(metham)、メタミドホス(methamidophos)、メタスルホカルブ(methasulfocarb)、メタゾール(methazole)、メトフロキサム(methfuroxam)、メチベンズロン(methibenzuron)、メチダチオン(methidathion)、メチオベンカルブ(methiobencarb)、メチオカルブ(methiocarb)、メチオピリスルフロン(methiopyrisulfuron)、メチオテパ(methiotepa)、メチオゾリン(methiozolin)、メチウロン(methiuron)、メトクロトホス(methocrotophos)、メトルカルブ(metholcarb)、メトメトン(methometon)、メトミル、メトプレン、メトプロトリン(methoprotryn)、メトプロトリン(methoprotryne)、メトキン-ブチル(methoquin-butyl)、メトトリン(methothrin)、メトキシクロル(methoxychlor)、メトキシフェノジド(methoxyfenozide)、メトキシフェノン(methoxyphenone)、メチルアホラート(methyl apholate)、臭化メチル、メチルオイゲノール、ヨウ化メチル、メチルイソチオシアネート、メチルパラチオン、メチルアセトホス(methylacetophos)、メチルクロロホルム、メチルジチオカルバミン酸(methyldithiocarbamic acid)、メチルダイムロン(methyldymron)、塩化メチレン、メチル-イソフェンホス(methyl-isofenphos)、メチルメルカプトホス(methylmercaptophos)、メチルメルカプトホスオキシド、メチルメルカプトホスチオール、メチル水銀ベンゾエート、メチル水銀ジシアンジアミド、メチル水銀ペンタクロロフェノキシド、メチルネオデカナミド(methylneodecanamide)、メチルニトロホス(methylnitrophos)、メチルトリアゾチオン(methyltriazothion)、メチオゾリン(metiozolin)、メチラム(metiram)、メチラム亜鉛(metiram-zinc)、メトベンズロン(metobenzuron)、メトブロムロン(metobromuron)、メトフルトリン(metofluthrin)、メトラクロール(metolachlor)、メトルカルブ(metolcarb)、メトメツロン(metometuron)、メトミノストロビン(metominostrobin)、メトスラム(metosulam)、メトキサジアゾン(metoxadiazone)、メトクスロン(metoxuron)、メトラフェノン(metrafenone)、メトリアム(metriam)、メトリブジン(metribuzin)、メトリホナート(metrifonate)、メトリホナート(metriphonate)、メトスルホバックス(metsulfovax)、メトスルフロン(metsulfuron)、メビンホス(mevinphos)、メキサカルバート(mexacarbate)、ミエシュウェイ(miechuwei)、ミエシュアン(mieshuan)、ミエウェンジュチ(miewenjuzhi)、ミルベメクチン(milbemectin)、ミルベマイシンオキシム(milbemycin oxime)、ミルネブ(milneb)、ミマ2ナン(mima2nan)、ミパフォックス(mipafox)、MIPC、マイレックス(mirex)、MNAF、モグチュン(moguchun)、モリネート(molinate)、モロスルタップ(molosultap)、モンフルオロトリン(momfluorothrin)、モナリド(monalide)、モニソウロン(monisouron)、モノアミトラズ(monoamitraz)、モノクロロ酢酸、モノクロトホス(monocrotophos)、モノリヌロン(monolinuron)、モノメハイポ(monomehypo)、モノスルフィラム(monosulfiram)、モノスルフロン(monosulfuron)、モノスルタップ(monosultap)、モヌロン(monuron)、モヌロン-TCA、モルファムコート(morfamquat)、モロキシジン(moroxydine)、モルホチオン(morphothion)、モルジド(morzid)、モキシデクチン(moxidectin)、MPMC、MSMA、MTMC、ムスカルア(muscalure)、ミクロブタニル(myclobutanil)、ミクロゾリン(myclozolin)、ミリシルアルコール、N-(エチル水銀)-p-トルエンスルホンアニリド、NAA、NAAm、ナバム(nabam)、ナフタロホス(naftalofos)、ナレド(naled)、ナフタレン、ナフタレンアセトアミド、ナフタル酸無水物、ナフタロホス(naphthalophos)、ナフトキシ酢酸、ナフチル酢酸、ナフチルインダン-1,3-ジオン類、ナフチルオキシ酢酸、ナプロアニリド(naproanilide)、ナプロパミド(napropamide)、ナプロパミド-M、ナプタラム(naptalam)、ナタマイシン(natamycin)、NBPOS、ネブレア(neburea)、ネブロン(neburon)、ネンドリン(nendrin)、ネオニコチン(neonicotine)、ニクロルホス(nichlorfos)、ニクロフェン(niclofen)、ニクロサミド(niclosamide)、ニコビフェン(nicobifen)、ニコスルフロン(nicosulfuron)、ニコチン、硫酸ニコチン、ニフルリジド(nifluridide)、ニッコマイシン類(nikkomycins)、NIP、ニピラクロフェン(nipyraclofen)、ニピラロフェン(nipyralofen)、ニテンピラム(nitenpyram)、ニチアジン(nithiazine)、ニトラリン(nitralin)、ニトラピリン(nitrapyrin)、ニトリラカルブ(nitrilacarb)、ニトロフェン(nitrofen)、ニトロフルオルフェン(nitrofluorfen)、ニトロスチレン、ニトロタール-イソプロピル(nitrothal-isopropyl)、ノボルミド(nobormide)、ノナノール、ノルボルミド(norbormide)、ノレア(norea)、ノルフルラゾン(norflurazon)、ノルニコチン(nornicotine)、ノルロン(noruron)、ノバルロン(n
ovaluron)、ノビフルムロン(noviflumuron)、NPA、ヌアリモル(nuarimol)、ヌラノン(nuranone)、OCH、オクタクロロジプロピルエーテル、オクチリノン(octhilinone)、o-ジクロロベンゼン、オフレース(ofurace)、オメトエート(omethoate)、o-フェニルフェノール、オルベンカルブ(orbencarb)、オルフラルア(orfralure)、オルソベンカーブ(orthobencarb)、オルト-ジクロロベンゼン、オルトスルファムロン(orthosulfamuron)、オリクタルア(oryctalure)、オリサストロビン(orysastrobin)、オリザリン(oryzalin)、オストール(osthol)、オストール(osthole)、オストラモン(ostramone)、オバトロン(ovatron)、オベックス(ovex)、オキサベトリニル(oxabetrinil)、オキサジアルギル(oxadiargyl)、オキサジアゾン(oxadiazon)、オキサジキシル(oxadixyl)、オキサメート(oxamate)、オキサミル(oxamyl)、オキサピラゾン(oxapyrazon)、オキサピラゾン(oxapyrazone)、オキサスルフロン(oxasulfuron)、オキサチアピプロリン(oxathiapiprolin)、オキサジクロメフォン(oxaziclomefone)、オキシン-銅(oxine-copper)、オキシン-Cu(oxine-Cu)、オキソリニン酸、オキスポコナゾール(oxpoconazole)、オキシカルボキシン(oxycarboxin)、オキシデメトン-メチル(oxydemeton-methyl)、オキシデプロホス(oxydeprofos)、オキシジスルホトン(oxydisulfoton)、オキシエナデニン(oxyenadenine)、オキシフルオルフェン(oxyfluorfen)、オキシマトリン(oxymatrine)、オキシテトラサイクリン、オキシチオキノクス(oxythioquinox)、PAC、パクロブトラゾール(paclobutrazol)、パイコングジング(paichongding)、パレトリン(pallethrine)、PAP、パラ-ジクロロベンゼン、パラフルロン(parafluron)、パラコート、パラチオン、パラチオン-メチル、パリノール(parinol)、パリスグリーン(Paris green)、PCNB、PCP、PCP-Na、p-ジクロロベンゼン、PDJ、ペブレート(pebulate)、ペジネックス(pedinex)、ペフラゾエート(pefurazoate)、ペラルゴン酸、ペンコナゾール(penconazole)、ペンシクロン(pencycuron)、ペンディメタリン(pendimethalin)、ペンフェナート(penfenate)、ペンフルフェン(penflufen)、ペンフルロン(penfluron)、ペノキサリン(penoxalin)、ペノキススラム(penoxsulam)、ペンタクロロフェノール、ペンタクロロフェニルラウレート、ペンタノクロル(pentanochlor)、ペンチオピラド(penthiopyrad)、ペントメトリン(pentmethrin)、ペントキサゾン(pentoxazone)、ペルクロルデコン(perchlordecone)、ペルフルイドン(perfluidone)、ペルメトリン(permethrin)、ペトキサミド(pethoxamid)、PHC、フェナマクリル(phenamacril)、フェナマクリル-エチル、フェナミノスルフ(phenaminosulf)、フェナジンオキシド(phenazine oxide)、フェネタカルブ(phenetacarbe)、フェニソファム(phenisopham)、フェンカプトン(phenkapton)、フェンメディファム(phenmedipham)、フェンメディファム-エチル、フェノベンズロン(phenobenzuron)、フェノチオール(phenothiol)、フェノトリン(phenothrin)、フェンプロキシド(phenproxide)、フェントエート(phenthoate)、尿素フェニル水銀(phenylmercuriurea)、酢酸フェニル水銀、塩化フェニル水銀、ピロカテコールのフェニル水銀誘導体、硝酸フェニル水銀、サリチル酸フェニル水銀、ホレート(phorate)、ホサセチム(phosacetim)、ホサロン(phosalone)、ホサメチン(phosametine)、ホサゼチム(phosazetim)、ホサゼチン(phosazetin)、ホスシクロチン(phoscyclotin)、ホスジフェン(phosdiphen)、ホセチル(phosethyl)、ホスホラン(phosfolan)、ホスホラン-メチル、ホスグリシン(phosglycin)、ホスメット(phosmet)、ホスニクロル(phosnichlor)、ホスファミド(phosphamide)、ホスファミドン(phosphamidon)、ホスフィン、ホスフィノトリシン(phosphinothricin)、ホスホカルブ(phosphocarb)、リン、ホスチン(phostin)、ホキシム(phoxim)、ホキシム-メチル、フタリド(phthalide)、フタロホス(phthalophos)、フタルスリン(phthalthrin)、ピカルブトラゾクス(picarbutrazox)、ピカリジン(picaridin)、ピクロラム(picloram)、ピコリナフェン(picolinafen)、ピコキシストロビン(picoxystrobin)、ピマリシン、ピンドン(pindone)、ピノキサデン(pinoxaden)、ピペラリン(piperalin)、ピペラジン、ピペロニルブトキシド、ピペロニルシクロネン(piperonyl cyclonene)、ピペロホス(piperophos)、ピプロクタニル(piproctanly)、ピプロクタニル(piproctanyl)、ピプロタール(piprotal)、ピリメタホス(pirimetaphos)、ピリミカルブ(pirimicarb)、ピリミニル(piriminil)、ピリミオキシホス(pirimioxyphos)、ピリミホス-エチル、ピリミホス-メチル、ピバル(pival)、ピバルジオン(pivaldione)、プリフェナート(plifenate)、PMA、PMP、ポリブテン類、ポリカーバメート、ポリクロルカンフェン(polychlorcamphene)、ポリエトキシキノリン(polyethoxyquinoline)、ポリオキシン D、ポリオキシン類、ポリオキソリム(polyoxorim)、ポリチアラン(polythialan)、亜ヒ酸カリウム、アジ化カリウム、シアン酸カリウム、エチルキサントゲン酸カリウム、ナフテン酸カリウム、カリウムポリスルフィド、チオシアン酸カリウム、pp'-DDT、プラレトリン(prallethrin)、プレコセン(precocene)I、プレコセンII、プレコセンIII、プレチラクロール(pretilachlor)、プリミドホス(primidophos)、プリミスルフロン(primisulfuron)、プロベナゾール(probenazole)、プロクロラズ(prochloraz)、プロクロノール(proclonol)、プロシアジン(procyazine)、プロシミドン(procymidone)、プロジアミン(prodiamine)、プロフェノホス(profenofos)、プロフルアゾール(profluazol)、プロフルラリン(profluralin)、プロフルトリン(profluthrin)、プロホキシジム(profoxydim)、プロフリット-アミニウム(profurite-aminium)、プログリナジン(proglinazine)、プロヘキサジオン(prohexadione)、プロヒドロジャスモン(prohydrojasmon)、プロマシル(promacyl)、プロメカルブ(promecarb)、プロメトン(prometon)、プロメトリン(prometryn)、プロメトリン(prometryne)、プロムリット(promurit)、プロナミド(pronamide)、プロパクロル(propachlor)、プロパホス(propafos)、プロパミジン(propamidine)、プロパモカルブ(propamocarb)、プロパニル(propanil)、プロパホス(propaphos)、プロパキザホップ(propaquizafop)、プロパルギット(propargite)、プロパルトリン(proparthrin)、プロパジン(propazine)、プロペタンホス(propetamphos)、プロファム(propham)、プロピコナゾール(propiconazole)、プロピジン(propidine)、プロピネブ(propineb)、プロピソクロール(propisochlor)、プロポクスル(propoxur)、プロポキシカルバゾン(propoxycarbazone)、プロピルイソム(propyl isome)、プロピリスルフロン(propyrisulfuron)、プロピザミド(propyzamide)、プロキナジド(proquinazid)、プロスレル(prosuler)、プロスルファリン(prosulfalin)、プロスルフォカルブ(prosulfocarb)、プロスルフロン(prosulfuron)、プロチダチオン(prothidathion)、プロチオカルブ(prothiocarb)、プロチオコナゾール(prothioconazole)、プロチオホス(prothifos)、プロトエート(prothoate)、プロトリフェンブト(protrifenbute)、プロキサン(proxan)、プリミドホス(prymidophos)、プリナクロール(prynachlor)、ソラレン(psoralen)、ソラレン(psoralene)、ピダノン(pydanon)、ピフルブミド(pyflubumide)、ピメトロジン(pymetrozine)、ピラカルボリド(pyracarbolid)、ピラクロホス(pyraclofos)、ピラクロニル(pyraclonil)、ピラクロストロビン(pyraclostrobin)、ピラフルフェン(pyraflufen)、ピラフルプロール(pyrafluprole)、ピラマット(pyramat)、ピラメトストロビン(pyrametostrobin)、ピラオキシストロビン(pyraoxystrobin)、ピラスルホトール(pyrasulfotole)、ピラジフルミド(pyraziflumid)、ピラゾレート(pyrazolate)、ピラゾリネート(pyrazolynate)、ピラゾン(pyrazon)、ピラゾホス(pyrazophos)、ピラゾスルフロン(pyrazosulfuron)、ピラゾチオン(pyrazothion)、ピラゾキシフェン(pyrazoxyfen)、ピレスメトリン(pyresmethrin)、ピレトリンI、ピレトリンII、ピレトリン類、ピリバムベンズ-イソプロピル(pyribambenz-isopropyl)、ピリバムベンズ-プロピル、ピリベンカルブ(pyribencarb)、ピリベンゾキシム(pyribenzoxim)、ピリブチカルブ(pyributicarb)、ピリクロール(pyriclor)、ピリダベン(pyridaben)、ピリダフォル(pyridafol)、ピリダリル(pyridalyl)、ピリダフェンチオン(pyridaphenthion)、ピリダフェンチオン(pyridaphenthione)、ピリデート(pyridate)、ピリジニトリル(pyridinitril)、ピリフェノクス(pyrifenox)、ピリフルキナゾン(pyrifluquinazon)、ピリフタリド(pyriftalid)、ピリメタホス(pyrimetaphos)、ピリメタニル(pyrimethanil)、ピリミカルブ(pyrimicarbe)、ピリミジフェン(pyrimidifen)、ピリミノバック(pyriminobac)、ピリミノストロビン(pyriminostrobin)、ピリミホス-エチル、ピリミホス-メチル、ピリミスルファン(pyrimisulfan)、ピリミテート(pyrimitate)、ピリヌロン(pyrinuron)、ピリオフェノン(pyriofenone)、ピリプロール(pyriprole)、ピリプロパノール(pyripropanol)、ピリプロキシフェン(pyriproxyfen)、ピリソキサゾール(pyrisoxazole)、ピリチオバック(pyrithiobac)、ピロラン(pyrolan)、ピロキロン(pyroquilon)、ピロキサスルフォン(pyroxasulfone)、ピロクススラム(pyroxsulam)、ピロキシクロル(pyroxychlor)、ピロキシフル(pyroxyfur)、キンカオスアン(qincaosuan)、キングクリング(qingkuling)、クワシア(quassia)、キナセトール(quinacetol)、キナルホス(quinalphos)、キナルホス-メチル、キナザミド(quinazamid)、キンクロラック(quinclorac)、キンコナゾール(quinconazole)、キンメラック(quinmerac)、キノクラミン(quinoclamine)、キノメチオネート(quinomethionate)、キノナミド(quinonamid)、キノチオン(quinothion)、キノキシフェン(quinoxyfen)、キンチオホス(quintiofos)、キントゼン(quintozene)、キザロホップ(quizalofop)、キザロホップ-P、クウェンチ(quwenzhi)、クイングジング(quyingding)、ラベンザゾール(rabenzazole)、ラフォキサニド(rafoxanide)、R-ジニコナゾール、レベミド(rebemide)、レグロン(reglone)、レンリデュロン(renriduron)、レスカルア(rescalure)、レスメトリン(resmethrin)、ロデタニル(rhodethanil)、ロドジャポニン(rhodojaponin)-III、リバビリン(ribavirin)、リムスルフロン(rimsulfuron)、リザゾール(rizazole)、R-メタラキシル(metalaxyl)、ロデタニル(rodethanil)、ロンネル(ronnel)、ロテノン(rotenone)、リアニア(ryania)、サバジラ(sabadilla)、サフルフェナシル(saflufenacil)、サイジュンマオ(saijunmao)、サイセントング(saisentong)、サリチルアニリド、サリフルオフェン(salifluofen)、サンギナリン(sanguinarine)、サントニン(santonin)、S-ビオアレトリン(bioallethrin)、シュラーダン(schradan)、シリロシド(scilliroside)、セブチラジン(sebuthylazine)、セクブメトン(secbumeton)、セダキサン(sedaxane)、セラメクチン(selamectin)、セミアミトラズ(semiamitraz)、セサメックス(sesamex)、セサモリン(sesamolin)、セソン(sesone)、セトキシジム(sethoxydim)、セビン(sevin)、シュアングジアアンカオリン(shuangjiaancaolin)、シュアングジアナンカオリン(shuangjianancaolin)、S-ヒドロプレン(hydroprene)、シデュロン(siduron)、シフミジブチ(sifumijvzhi
)、シグルア(siglure)、シラフルオフェン(silafluofen)、シラトラン(silatrane)、シリカエアロゲル、シリカゲル、シルチオファム(silthiofam)、シルチオファム(silthiopham)、シルチオファン(silthiophan)、シルベックス(silvex)、シマジン(simazine)、シメコナゾール(simeconazole)、シメトン(simeton)、シメトリン(simetryn)、シメトリン(simetryne)、シントフェン(sintofen)、S-キノプレン(kinoprene)、消石灰、SMA、S-メトプレン、S-メトラクロール(S-metolachlor)、亜ヒ酸ナトリウム、アジ化ナトリウム、塩素酸ナトリウム、シアン化ナトリウム、フッ化ナトリウム、フルオロ酢酸ナトリウム、ヘキサフルオロケイ酸ナトリウム、ナフテン酸ナトリウム、ナトリウムo-フェニルフェノキシド、ナトリウムオルトフェニルフェノキシド、ナトリウムペンタクロロフェナート、ナトリウムペンタクロロフェノキシド、ポリ硫化ナトリウム、ケイフッ化ナトリウム、テトラチオ炭酸ナトリウム、チオシアン酸ナトリウム、ソラン(solan)、ソファミド(sophamide)、スピネトラム(spinetoram)、スピノサド(spinosad)、スピロジクロフェン(spirodiclofen)、スピロメシフェン(spiromesifen)、スピロテトラマト(spirotetramat)、スピロキサミン(spiroxamine)、スチロホス(stirofos)、ストレプトマイシン、ストリキニーネ、スルカト−ル(sulcatol)、スルコフロン(sulcofuron)、スルコトリオン(sulcotrione)、スルファレート(sulfallate)、スルフェントラゾン(sulfentrazone)、スルフィラム(sulfiram)、スルフルラミド(sulfluramid)、スルホジアゾール(sulfodiazole)、スルホメツロン(sulfometuron)、スルホサート(sulfosate)、スルホスルフロン(sulfosulfuron)、スルホテップ(sulfotep)、スルホテップ(sulfotepp)、スルホキサフロル(sulfoxaflor)、スルホキシド(sulfoxide)、スルホキシム(sulfoxime)、硫黄、硫酸、フッ化スルフリル、スルグリカピン(sulglycapin)、スルホサート(sulphosate)、スルプロホス(sulprofos)、スルトロペン(sultropen)、スウェップ(swep)、タウ-フルバリネート(fluvalinate)、タブロン(tavron)、タジムカルブ(tazimcarb)、TBTO、TBZ、TCA、TCBA、TCMTB、TCNB、TDE、テブコナゾール(tebuconazole)、テブフェノジド(tebufenozide)、テブフェンピラド(tebufenpyrad)、テブフロキン(tebufloquin)、テブピリムホス(tebupirimfos)、テブタム(tebutam)、テブチウロン(tebuthiuron)、テクロフタラム(tecloftalam)、テクナゼン(tecnazene)、テコラム(tecoram)、テディオン(tedion)、テフルベンズロン(teflubenzuron)、テフルトリン(tefluthrin)、テフリルトリオン(tefuryltrione)、テムボトリオン(tembotrione)、テメホス(temefos)、テメホス(temephos)、テパ(tepa)、TEPP、テプラロキシジム(tepraloxydim)、テプロロキシジム(teproloxydim)、テラレトリン(terallethrin)、テルバシル(terbacil)、テルブカルブ(terbucarb)、テルブクロル(terbuchlor)、テルブホス(terbufos)、テルブメトン(terbumeton)、テルブチラジン(terbuthylazine)、テルブトール(terbutol)、テルブトリン(terbutryn)、テルブトリン(terbutryne)、テラクロール(terraclor)、テラマイシン(terramicin)、テラマイシン(terramycin)、テトシクラシス(tetcyclacis)、テトラクロロエタン、テトラクロルビンホス、テトラコナゾール(tetraconazole)、テトラジホン(tetradifon)、テトラジスル(tetradisul)、テトラフルロン(tetrafluron)、テトラメトリン(tetramethrin)、テトラメチルフルトリン(tetramethylfluthrin)、テトラミン(tetramine)、テトラナクチン(tetranactin)、テトラニリプロール(tetraniliprole)、テトラピオン(tetrapion)、テトラスル(tetrasul)、硫酸タリウム(thallium sulfate)、硫酸タリウム(thallous sulfate)、テニルクロール(thenylchlor)、シータ-シペルメトリン(cypermethrin)、チアベンダゾール、チアクロプリド(thiacloprid)、チアジアジン(thiadiazine)、チアジフルオル(thiadifluor)、チアメトキサム(thiamethoxam)、チアメツロン(thiameturon)、チアプロニル(thiapronil)、チアザフルロン(thiazafluron)、チアザフルロン(thiazfluron)、チアゾン(thiazone)、チアゾピル(thiazopyr)、チクロホス(thicrofos)、チシオフェン(thicyofen)、チジアジミン(thidiazimin)、チジアズロン(thidiazuron)、チエンカルバゾン(thiencarbazone)、チフェンスルフロン(thifensulfuron)、チフルザミド(thifluzamide)、チメロサール、チメット(thimet)、チオベンカルブ(thiobencarb)、チオカルボキシム(thiocarboxime)、チオクロルフェンフィム(thiochlorfenphim)、チオクロルフェンフィム(thiochlorphenphime)、チオシアナトジニトロベンゼン類、チオシクラム(thiocyclam)、チオダン(thiodan)、チオジアゾール-銅、チオジカルブ(thiodicarb)、チオファノカルブ(thiofanocarb)、チオファノックス(thiofanox)、チオフルオキシメート(thiofluoximate)、チオヘンパ(thiohempa)、チオメルサール(thiomersal)、チオメトン(thiometon)、チオナジン(thionazin)、チオファネート(thiophanate)、チオファネート-エチル、チオファネート-メチル、チオホス(thiophos)、チオキノックス(thioquinox)、チオセミカルバジド、チオスルタップ(thiosultap)、チオテパ、チオキサミル(thioxamyl)、チラム(thiram)、チウラム(thiuram)、ツリンギエンシン(thuringiensin)、チアベンダゾール(tiabendazole)、チアジニル(tiadinil)、チアフェナシル(tiafenacil)、チアオジエアン(tiaojiean)、TIBA、チファトール(tifatol)、チオカルバジル(tiocarbazil)、チオクロリム(tioclorim)、チオキサザフェン(tioxazafen)、チオキシミド(tioxymid)、チルパート(tirpate)、TMTD、トルクロホス-メチル(tolclofos-methyl)、トルフェンピラド(tolfenpyrad)、トルプロカルブ(tolprocarb)、トルピラレート(tolpyralate)、トリフルアニド(tolyfluanid)、トリルフルアニド(tolylfluanid)、トリル水銀アセテート、トマリン(tomarin)、トプラメゾン(topramezone)、トキサフェン(toxaphene)、TPN、トラルコキシジム(tralkoxydim)、トラロシトリン(tralocythrin)、トラロメトリン(tralomethrin)、トラロピリル(tralopyril)、トランスフルトリン(transfluthrin)、トランスペルメトリン(transpermethrin)、トレタミン(tretamine)、トリアコンタノール(triacontanol)、トリアジメホン(triadimefon)、トリアジメノール(triadimenol)、トリアファモン(triafamone)、トリアレート(triallate)、トリ-アレート(tri-allate)、トリアミホス(triamiphos)、トリアペンテノール(triapenthenol)、トリアラテン(triarathene)、トリアリモール(triarimol)、トリアスルフロン(triasulfuron)、トリアザメート(triazamate)、トリアズブチル(triazbutil)、トリアジフラム(triaziflam)、トリアゾホス(triazophos)、トリアゾチオン(triazothion)、トリアゾキシド(triazoxide)、三塩基塩化銅、三塩基硫酸銅、トリベヌロン(tribenuron)、トリブホス(tribufos)、トリブチルスズオキシド、トリカンバ(tricamba)、トリクラミド(trichlamide)、トリクロピル(trichlopyr)、トリクロルホン(trichlorfon)、トリクロルメタホス-3(trichlormetaphos-3)、トリクロロナート(trichloronat)、トリクロロナート(trichloronate)、トリクロロトリニトロベンゼン類、トリクロルホン(trichlorphon)、トリクロピル(triclopyr)、トリクロピリカルブ(triclopyricarb)、トリクレゾール(tricresol)、トリシクラゾール(tricyclazole)、水酸化トリシクロヘキシルスズ、トリデモルフ(tridemorph)、トリジファン(tridiphane)、トリエタジン(trietazine)、トリフェンモルフ(trifenmorph)、トリフェノホス(trifenofos)、トリフロキシストロビン(trifloxystrobin)、トリフロキシスルフロン(trifloxysulfuron)、トリフルジモキサジン(trifludimoxazin)、トリフルメゾピリム(triflumezopyrim)、トリフルミゾール(triflumizole)、トリフルムロン(triflumuron)、トリフルラリン(trifluralin)、トリフルスルフロン(triflusulfuron)、トリホップ(trifop)、トリホプシム(trifopsime)、トリホリン(triforine)、トリヒドロキシトリアジン、トリメドルア(trimedlure)、トリメタカルブ(trimethacarb)、トリメツロン(trimeturon)、トリネクサパック(trinexapac)、トリフェニルスズ、トリプレン(triprene)、トリプロピンダン(tripropindan)、トリプトリド(triptolide)、トリタック(tritac)、トリチアラン(trithialan)、トリチコナゾール(triticonazole)、トリトスルフロン(tritosulfuron)、トランク-コール(trunc-call)、ツオイェリン(tuoyelin)、ウニコナゾール(uniconazole)、ウニコナゾール-P、ウルバシド(urbacide)、ウレデパ(uredepa)、バレレート(valerate)、バリダマイシン、バリダマイシンA、バリフェナレート(valifenalate)、バロン(valone)、バミドチオン(vamidothion)、バンガード(vangard)、バニリプロール(vaniliprole)、ベルノレート(vernolate)、ビンクロゾリン(vinclozolin)、ビタミンD3、ワルファリン(warfarin)、キシアオコングリウリン(xiaochongliulin)、キシンジュナン(xinjunan)、キシウォジュナン(xiwojunan)、キシウォジュンチ(xiwojunzhi)、XMC、キシラクロール(xylachlor)、キシレノール類、キシリルカルブ(xylylcarb)、キシミアゾール(xymiazole)、イシジング(yishijing)、ザリラミド(zarilamid)、ゼアチン(zeatin)、ゼングキシアオアン(zengxiaoan)、ゼングキシアオリン(zengxiaolin)、ゼータ-シペルメトリン、ナフテン酸亜鉛、リン化亜鉛、亜鉛チアゾール(zinc thiazole)、亜鉛チオゾール(zinc thiozole)、亜鉛トリクロロフェネート(zinc trichlorophenate)、亜鉛トリクロロフェノキシド(zinc trichlorophenoxide)、ジネブ(zineb)、ジラム(ziram)、ゾラプロホス(zolaprofos)、ズークマリン(zoocoumarin)、ゾキサミド(zoxamide)、ズオアンジュンチ(zuoanjunzhi)、ズオカオアン(zuocaoan)、ズオジュンチ(zuojunzhi)、ズオミフアングロング(zuomihuanglong)、α-クロロヒドリン、α-エクジソン(ecdysone)、α-ムルチストリアチン(multistriatin)、α-ナフタレン酢酸、及びβ-エクジソン;
(a) N-(3-クロロ-1-(ピリジン-3-イル)-1H-ピラゾール-4-イル)-N-エチル-3-((3,3,3-トリフルオロプロピル)チオ)プロパンアミド(以下「AI-1」)
まう領域、建造物の内部表面または外部表面(穀物が貯蔵される場所など)、建造物に使用される建設用材料(含浸木材など)、ならびに建造物の周りの土壌であってもよい。
アセフェート、アザメチホス、アジンホス-エチル、アジンホス-メチル、カズサホス、
クロレトキシホス、クロルフェンビンホス、クロルメホス、クロルピリホス、クロルピリホス-メチル、クマホス、シアノホス、デメトン-S-メチル、ダイアジノン、ジクロルボス/DDVP、ジクロトホス、ジメトエート、ジメチルビンホス、ジスルホトン、EPN、エチオン、エトプロホス、ファムフル、フェナミホス、フェニトロチオン、フェンチオン、ホスチアゼート、ヘプテノホス、イミシアホス、イソフェンホス、イソプロピルO-(メトキシアミノチオ-ホスホリル)サリチレート、イソキサチオン、マラチオン、メカルバム、メタミドホス、メチダチオン、メビンホス、モノクロトホス、ナレド、オメトエート、オキシデメトン-メチル、パラチオン、パラチオン-メチル、フェントエート、ホレート、ホサロン、ホスメット、ホスファミドン、ホキシム、ピリミホス-メチル、プロフェノホス、プロペタンホス、プロチオホス、ピラクロホス、ピリダフェンチオン、キナルホス、スルホテップ、テブピリムホス、テメホス、テルブホス、テトラクロルビンホス、チオメトン、トリアゾホス、トリクロルホン、バミドチオンを含む。
(2) GABA作動性クロライドチャネルアンタゴニストであり、以下の活性成分、クロルデン、エンドスルファン、エチプロール、及びフィプロニルを含む。
(3) ナトリウムチャネルモジュレータであり、以下の活性成分、アクリナトリン、アレトリン、d-シス-トランスアレトリン、d-トランスアレトリン、ビフェントリン、ビオアレトリン、ビオアレトリンS-シクロペンテニル、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、シフェノトリン
[(1R)-トランス-異性体]、デルタメトリン、エンペントリン、[(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(ジョチュウギク)、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、テトラメトリン[(1R)-異性体]、トラロメトリン、及びトランスフルトリン、ならびにメトキシクロルを含む。
(4) ニコチン性アセチルコリン受容体(nAChR)アゴニストであり、以下の活性成分、
(4A) アセタミプリド、クロチアニジン、ジノテフラン、イミダクロプリド、ニテンピラム、チアクロプリド、チアメトキサム、
(4B) ニコチン、
(4C) スルホキサフロール、
(4D) フルピラジフロン、
(4E) トリフルメゾピリム及びジクロロメゾチアズを含む。
(5) ニコチン性アセチルコリン受容体(nAChR)アロステリック活性化因子であり、
以下の活性成分、スピネトラム、及びスピノサドを含む。
(6) クロライドチャネル活性化因子であり、以下の活性成分、アバメクチン、エマメクチン安息香酸塩、レピメクチン、及びミルベメクチンを含む。
(7) 幼若ホルモン模倣物であり、以下の活性成分、ヒドロプレン、キノプレン、メトプレン、フェノキシカルブ、及びピリプロキシフェンを含む。
(8) 多種非特異性(多部位)阻害剤であり、以下の活性成分、臭化メチル、クロロピクリン、フッ化スルフリル、ボラックス、及び吐酒石を含む。
(9) 弦音器官のモジュレータであり、以下の活性成分、ピメトロジン、及びフロニカミドを含む。
(10) ダニ増殖阻害剤であり、以下の活性成分、クロフェンテジン、ヘキシチアゾクス、ジフロビダジン、及びエトキサゾールを含む。
(11) 昆虫中腸膜の微生物撹乱剤であり、以下の活性成分、バチルス・チューリンゲンシス亜種(Bacillus thuringiensis subsp.) イスラエレンシス、バチルス・チューリンゲンシス亜種(Bacillus thuringiensis subsp.)アイザワイ(aizawai)、バチルス・チューリンゲンシス亜種(Bacillus thuringiensis subsp.) クルスターキ(Kurstaki)、バチルス・チューリンゲンシス亜種(Bacillus thuringiensis subsp.)テネブリオネニス(tenebrionenis)、Bt作物タンパク質(Cry1Ab、Cry1Ac、Cry1Fa、Cry1A.105、Cry2Ab、Vip3A、mCry3A、Cry3Ab、Cry3Bb、Cry34Ab1/Cry35Ab1)、及びバチルス・スファエリクス(Bacillus sphaericus)を含む。
(12) ミトコンドリアATP合成酵素阻害剤であり、以下の活性成分、テトラジホン、プロパルギット、アゾシクロチン、シヘキサチン、フェンブタチンオキシド、及びジアフェンチウロンを含む。
(13) プロトン勾配の乱れを介した酸化的リン酸化の脱共役剤であり、以下の活性成分、クロルフェナピル、DNOC、及びスルフルラミドを含む。
(14) ニコチン性アセチルコリン受容体(nAChR)チャネル遮断剤であり、以下の活性成分、ベンスルタップ、カルタップ塩酸塩、チオシクラム、及びチオスルタップ-ナトリウムを含む。
(15) キチン生合成阻害剤、タイプ0であり、以下の活性成分、ビストリフルロン、クロルフルアズロン、ジフルベンズロン、フルシクロクスロン、フルフェノクスロン、ヘキサフルムロン、ルフェヌロン、ノバルロン、ノビフルムロン、テフルベンズロン、及びトリフルムロンを含む。
(16) キチン生合成阻害剤、タイプ1であり、以下の活性成分、ブプロフェジンを含む。
(17) 双翅目の脱皮撹乱剤であり、以下の活性成分、シロマジンを含む。
(18) エクジソン受容体アゴニストであり、以下の活性成分、クロマフェノジド、ハロフェノジド、メトキシフェノジド、及びテブフェノジドを含む。
(19) オクトパミン受容体アゴニストであり、以下の活性成分、アミトラズを含む。
(20) ミトコンドリア複合体III電子伝達阻害剤であり、以下の活性成分、ヒドラメチルノン、アセキノシル、及びフルアクリピリムを含む。
(21) ミトコンドリア複合体I電子伝達阻害剤であり、以下の活性成分、フェナザキン、フェンピロキシメート、ピリミジフェン、ピリダベン、テブフェンピラド、トルフェンピラド、及びロテノンを含む。
(22) 電位依存性ナトリウムチャネル遮断剤であり、以下の活性成分、インドキサカルブ、及びメタフルミゾンを含む。
(23) アセチルCoAカルボキシラーゼ阻害剤であり、以下の活性成分、スピロジクロフェン、スピロメシフェン、及びスピロテトラマトを含む。
(24) ミトコンドリア複合体IV電子伝達阻害剤であり、以下の活性成分、リン化アルミニウム、リン化カルシウム、ホスフィン、リン化亜鉛、及びシアニドを含む。
(25) ミトコンドリア複合体II電子伝達阻害剤であり、以下の活性成分、シエノピラフェン、及びシフルメトフェンを含む。
(28) リアノジン受容体モジュレータであり、以下の活性成分、クロラントラニリプロール、シアントラニリプロール、及びフルベンジアミドを含む。
群26及び群27は、分類スキームの本バージョンには割り当てられていない。さらに、未知または不明の作用機序の活性成分を含有する群UNがある。この群は、以下の活性成分、アザジラクチン、ベンゾキシメート、ビフェナゼート、ブロモプロピレート、キノメチオナト、氷晶石、ジコホル、ピリダリル、及びピリフルキナゾンを含む。
さらなる例は、以下に分類される害虫である。
(1) 鋏角亜門、多足亜門、及び六脚亜門。
(2) 蛛形綱、結合網、及び昆虫綱。
(3) シラミ目。特定の属の非網羅的なリストには、限定されないが、ハエマトピヌス属種(Haematopinus spp.)、ホプロプレウラ属種(Hoplopleura spp.)、リノグナツス属種(Linognathus spp.)、ペディクルス属種(Pediculus spp.)、ポリプラクス属種(Polyplax spp.)、ソレノポテス属種(Solenopotes spp.)、及びネオハエマトピニス属種(Neohaematopinis spp.)が含まれる。特定の種の非網羅的なリストには、限定されないが、ハエマトピヌス・アシニ(Haematopinus asini)、ハエマトピヌス・スイス(Haematopinus suis)、リノグナツス・セトスス(Linognathus setosus)、リノグナツス・オビルス(Linognathus ovillus)、ペジクルス・フマヌス・カピチス(Pediculus humanus capitis)、ペジクルス・フマヌス・フマヌス(Pediculus humanus humanus)、及びプチルス・プビス(Pthirus pubis)が含まれる。
(4) 鞘翅目。特定の属の非網羅的なリストには、限定されないが、アカントセリデス属種(Acanthoscelides spp.)、アグリオテス属種(Agriotes spp.)、アントノムス属種(Anthonomus spp.)、アピオン属種(Apion spp.)、アポゴニア属種(Apogonia spp.)、アラエセルス属種(Araecerus spp.)、アウラコフォラ属種(Aulacophora spp.)、ブルクス属種(Bruchus spp.)、セロステルナ属種(Cerosterna spp.)、セロトマ属種(Cerotoma spp.)、セウトリンクス属種(Ceutorhynchus spp.)、カエトクネマ属種(Chaetocnema spp.)、コラスピス属種(Colaspis spp.)、クテニセラ属種(Ctenicera
spp.)、クルクリオ属種(Curculio spp.)、シクロセファラ属種(Cyclocepahla spp.)、ジアブロチカ属種(Diabrotica spp.)、ジノデルス属種(Dinoderu spp.)、グナトセルス属種(Gnathocerus spp.)、ヘミコエルス属種(Hemicoelus spp.)、ヘテロボストリクス属種(Heterobostruchus spp.)、ヒペラ属種(Hypera spp.)、イプス属種(Ips spp.)、リクツス属種(Lyctus spp.)、メガセリス属種(Megascelis spp.)、メリゲテス属種(Meligethes spp.)、メジウム属種(Mezium spp.)、ニプタス属種(Niptus spp.)、オチオリンクス属種(Otiorhynchus spp.)、パントモルス属種(Pantomorus spp.)、フィロファガ属種(Phyllophaga spp.)、フィロトレタ属種(Phllotreta spp.)、プチヌス属種(Ptinus spp.)、リゾトログス属種(Rhizotrogus spp.)、リンキテス属種(Rhynchites spp.)、リンコフォルス属種(Rhynchophorus spp.)、スコリツス属種(Scolytus spp.)、スフェノフォルス属種(Sphenophorus spp.)、シトフィルス属種(Sitophilus spp.)、テネブリオ属種(Tenebrio spp.)、及びトリボリウム属種(Tribolium spp.)が含まれる。特定の種の非網羅的なリストには、限定されないが、アカントセリデス・オブテクツス(Acanthoscelides obtectus)、アグリルス・プラニペンニス(Agrilus planipennis)、アハスベルス・アドベナ(Ahasverus advena)、アルフィトビウス・ジアペリヌス(Alphitobius diaperinus)、アノプロフォラ ・グラブリペンニス(A
noplophora glabripennis)、アントノムス・グランジス(Anthonomus grandis)、アントレヌス・ベルバシ(Anthrenus verbasci)、アントレヌス・ファルビペス(Anthrenus falvipes)、アタエニウス・スプレツルス(Ataenius spretulus)、アトマリア・リネアリス(Atomaria linearis)、ヒメカツオブシムシ(Attagenus unicolor)、ボチノデレス・プンクチベントリス(Bothynoderes punctiventris)、ブルクス・ピソルム(Bruchus pisorum)、カロソブルクス・マクラツス(Callosobruchus maculatus)、カルポフィルス・ヘミプテルス(Carpophilus hemipterus)、カッシダ・ビッタタ(Cassida vittata)、タバコヒラタムシ(Cathartus quadricollis)、セロトマ・トリフルカタ(Cerotoma trifurcata)、セウトリンクス・アシミリス(Ceutorhynchus assimilis)、セウトリンクス・ナピ(Ceutorhynchus napi)、コノデルス・スカラリス(Conoderus scalaris)、コノデルス・スチグモスス(Conoderus stigmosus)、コノトラケルス・ネヌファル(Conotrachelus nenuphar)、コチニス・ニチダ(Cotinis nitida)、クリオセリス・アスパラギ(Crioceris asparagi)、クリプトレステス・フェルギネウス(Cryptolestes ferrugineus)、クリプトレステス・プシルス(Cryptolestes pusillus)、クリプトレステス・ツルシクス(Cryptolestes turcicus)、シリンドロコプツルス・アデスペルスス(Cylindrocopturus adspersus)、デポラウス・マルギナツス(Deporaus marginatuss)、デルメステス・ラルダリウス(Dermestes lardarius)、デルメステス・マクラツス(Dermestes maculatus)、エピラクナ・バリベスチス(Epilachna varivestis)、エウブリレタ・ペルタタ(Euvrilletta peltata)、ファウスチヌス・クバエ(Faustinus cubae)、ヒロビウス・パレス(Hylobius pales)、ヒロトルペス・バジュルス(Hylotrupes bajulus)、ヒペラ・ポスチカ(Hypera postica)、ヒポテネムス・ハムペイ(Hypothenemus hampei)、ラシオデルマ・セリコルネ(Lasioderma serricorne)、レプチノタルサ・デセムリネアタ(Leptionotarsa decemkineata)、リモニウス・カヌス(Limonius canus)、リオゲニス・フスクス(Liogenys fuscus)、リオゲニス・スツラリス(Liogenys suturalis)、リソルホプトルス・オリゾフィルス(Lissorhoptrus oryzophilus)、ホソチビコクヌスト(Lophocateres pusillus)、リクタス・プラニコリス(Lyctus planicollis)、マエコラスピス・ジョリベチ(Maecolaspis joliveti)、メラノツス・コムニス(Melanotus communis)、メリゲテス・アエネウス(Meligethes aeneus)、メロロンタ・メロロンタ(Melolontha melolontha)、アカアシホシカムシ(Necrobia rufipes)、オベレア・ブレビス(Oberea brevis)、オベレア・リネアリス(Oberea linearis)、オリクテス・リノセロス(Oryctes rhinoceros)、オリザエフィルス・メルカトル(Oryzaephilus
mercator)、オリザエフィルス・スリナメンシス(Oryzaephilus surinamensis)、オウレマ・メラノプス(Oulema melanopus)、オウレマ・オリザエ(Oulema oryzae)、フィロファガ・クヤバナ(Phyllophaga cuyabana)、ポリカオン・ストウティ(Polycaon stoutti)、ポピリア・ジャポニカ(Popillia japonica)、プロステファヌス・トルンカツス(Prostephanus truncatus)、リゾペルタ・ドミニカ(Rhyzopertha dominica)、シトナ・リネアツス(Sitona lineatus)、シトフィルス・グラナリウス(Sitophilus granarius)、シトフィルス・オリザエ(Sitophilus oryzae)、シトフィルス・ゼアマイス(Sitophilus zeamais)、ステゴビウム・パニセウム(Stegobium paniceum)、コクヌスト(Tenebroides mauritanicus)、トリボリウム・カスタネウム(Trinolium castaneum)、トリボリウム・コンフスム(Trinolium confusum)、トロゴデルマ・グラナリウム(Trogoderma granarium)、トロゴデルマ・バリアビレ(Trogoderma variabile)、キセストビウム・ルフォビロスム(Xestobium rufovillosum)、及びザブルス・テネブリオイデス(Zabrus tenebrioides)が含まれる。
(5) 革翅目。特定の種の非網羅的なリストには、限定されないが、フォルフィクラ・アウリクラリア(Forficula auricularia)が含まれる。
(6) ゴキブリ目。特定の種の非網羅的なリストには、限定されないが、ブラッテラ・ゲルマニカ(Blattella germanica)、ブラッテラ・アサヒナイ(Blattella asahinai)、ブラッタ・オリエンタリス(Blatta orientalis)、ブラッタ・ラテラリス(Blatta lateralis)、パルコブラッタ・ペンシルバニカ(Parcoblatta pennsylvanica)、ペリプ
ラネタ・アメリカナ(Periplaneta americana)、ペリプラネタ・アウストララシアエ(Periplaneta australasiae)、ペリプラネタ・ブルンネア(Periplaneta brunnea)、ペリプラネタ・フリギノサ(Periplaneta fuliginosa)、ピクノスセルス・スリナメンシス(Pycnoscelus surinamensis)、及びスペラ・ロンギパルパ(Supella longipalpa)が含まれる。
(7) 双翅目。特定の属の非網羅的なリストには、限定されないが、アエデス属種(Aedes spp.)、アグロミザ属種(Agromyza spp.)、アナストレファ属種(Anastrepha spp.)、アノフェレス属種(Anopheles spp.)、バクトロセラ属種(Bactrocera spp.)、セラチチス属種(Ceratitis spp.)、クリソプス属種(Chrysops spp.)、コクリオミイア属種(Cochliomyia spp.)、コンタリニア属種(Contarinia spp.)、クレクス属種(Culex spp.)、クリコイデス属種(Culicoides spp.)、ダシネウラ属種(Dasineura spp.)、デリア属種(Delia spp.)、ドロソフィラ属種(Drosophila spp.)、ファンニア属種(Fannia spp.)、ヒレミイア属種(Hylemyia spp.)、リリオミザ属種(Liriomyza spp.)、ムスカ属種(Musca spp.)、ホルビア属種(Phorbia spp.)、ポレニア属種(Pollenia spp.)、サイコダ属種(Psychoda spp.)、シムリウム属種(Simulium spp.)、タバヌス属種(Tabanus spp.)、及びチプラ属種(Tipula spp.)が含まれる。特定の種の非網羅的なリストには、限定されないが、アグロミザ・フロンテラ(Agromyza frontella)、アナストレファ・サスペンサ(Anastrepha suspensa)、アナストレファ・ルーデンス(Anastrepha ludens)、アナストレファ・オブリカ(Anastrepha obliqua)、バクトロセラ・ククルビタエ(Bactrocera cucurbitae)、バクトロセラ・ドーサリス(Bactrocera dorsalis)、バクトロセラ・インバデンス(Bactrocera invadens)、バクトロセラ・ゾナータ(Bactrocera zonata)、セラチチス・カピタタ(Ceratitis capitata)、ダシネウラ・ブラッシカエ(Dasineura brassicae)、デリア・プラツラ(Delia platura)、ファンニア・カニクラリス(Fannia canicularis)、ファンニア・スカラリス(Fannia scalaris)、ガステロフィルス・インテスティナリス(Gasterophilus intestinalis)、グラシリア・ペルセアエ(Gracillia perseae)、ハエマトビア・イリタンス(Haematobia irritans)、ヒポデルマ・リネアツム(Hypoderma lineatum)、リリオミザ・ブラッシカエ(Liriomyza brassicae)、メロファグス・オビヌス(Melophagus ovinus)、ムスカ・オータムナリス(Musca autumnalis)、ムスカ・ドメスチカ(Musca domestica)、 オエストルス・オビス(Oestrus ovis)、オシネラ・フリト(Oscinella frit)、ペゴミア・ベタエ(Pegomya betae)、ピオフィラ・カセイ(Piophila casei)、プシラ・ロサエ(Psila rosae)、ラゴレチス・セラシ(Rhagoletis cerasi)、ラゴレチス・ポモネラ(Rhagoletis pomonella)、ラゴレチス・メンダクス(Rhagoletis mendax)、シトディプロシス・モセラーナ(Sitodiplosis mosellana)、及びストモキス・カルシトランス(Stomoxys calcitrans)が含まれる。
(8) 半翅目。特定の属の非網羅的なリストには、限定されないが、アデルゲス属種(Adelges spp.)、アウラカスピス属種(Aulacaspis spp.)、アフロフォラ属種(Aphrophora spp.)、アフィス属種(Aphis spp.)、ベミシア属種(Bemisia spp.)、セロプラステス属種(Ceroplastes spp.)、キオナスピス属種(Chionaspis spp.)、クリソムファルス属種(Chrysomphalus spp.)、コックス属種(Coccus spp.)、エンポアスカ属種(Empoasca spp.)、エウシスツス属種(Euschistus spp.)、レピドサフェス属種(Lepidosaphes spp.)、ラギノトムス属種(Lagynotomus spp.)、リグス属種(Lygus spp.)、マクロシフム属種(Macrosiphum spp.)、ネホテッチキス属種(Nephotettix spp.)、ネザラ属種(Nezara spp.)、ニラパルバタ属種(Nilaparvata spp.)、フィラエヌス属種(Philaenus spp.)、フィトコリス属種(Phytocoris spp.)、ピエゾドルス属種(Piezodorus spp.)、プラノコックス属種(Planococcus spp.)、プセウドコックス属種(Pseudococcus spp.)、ロパロシフム属種(Rhopalosiphum spp.)、サイセチア属種(Saissetia spp.)、テリオアフィス属種(Therioaphis spp.)、トウメイエラ属種(Toumeyella spp.)、トキソプテラ属種(Toxoptera spp.)、トリアレウロデス属種(Trialeurodes
spp.)、トリアトマ属種(Triatoma spp.)、及びウナスピス属種(Unaspis spp.)が含
まれる。特定の種の非網羅的なリストには、限定されないが、アクロステルヌム・ヒラレ(Acrosternum hilare)、アシルトシフォン・ピスム(Acyrthosiphon pisum)、アレイロデス・プロレテラ(Aleyrodes proletella)、アレウロジクス・ジスペルスス(Aleurodicus dispersus)、アレウロスリクス・フッコスス(Aleurothrixus floccosus)、アムラスカ・ビグツラ・ビグツラ(Amrasca biguttula biguttula)、アオニジエラ・アウランチイ(Aonidiella aurantii)、アフィス・ゴシピイ(Aphis gossypii)、アフィス・グリシネス(Aphis glycines)、アフィス・ポミ(Aphis pomi)、アウラコルスム・ソラニ(Aulacorthum solani)、バクテリセラ・コクケレリ(Bactericera cockerelli)、バグラダ・ヒラリス(Bagrada hilaris)、ベミシア・アルゲンチフォリイ(Bemisia argentifolii)、ベミシア・タバチ(Bemisia tabaci)、ブリッスス・レウコプテルス(Blissus leucopterus)、ボイセア・トリヴィタタ(Boisea trivittata)、ブラキコリネラ・アスパラギ(Brachycorynella asparagi)、ブレベンニア・レヒ(Brevennia rehi)、ブレビコリネ・ブラシカエ(Brevicoryne brassicae)、カコプシラ・ピリ(Cacopsylla pyri)、カコプシラ・ピリコラ(Cacopsylla pyricola)、カロコリス・ノルベギクス(Calocoris norvegicus)、セロプラステス・ルベンス(Ceroplastes rubens)、シメクス・ヘミプテルス(Cimex hemipterus)、シメクス・レクツラリウス(Cimex lectularius)、ダグベルツス・ファシアツス(Dagbertus fasciatus)、ジケロプス・フルカツス(Dichelops furcatus)、ジウラフィス・ノクシア(Diuraphis noxia)、ジアフォリナ・シトリ(Diaphorina citri)、ジサフィス・プランタギネア(Dysaphis plantaginea)、ジルデルクス・スツレルス(Dysdercus suturellus)、エデッサ・メジタブンダ(Edessa meditabunda)、エリオソマ・ラニゲルム(Eriosoma lanigerum)、エウリガステル・マウラ(Eurygaster maura)、エウシスツス・コンスペルサス(Euschistus conspersus)、エウシスツス・ヘロス(Euschistus heros)、エウシスツス・セルブス(Euschistus servus)、ハリオモルファ・ハリス(Halyomorpha halys)、ヘロペルチス・アントニイ(Helopeltis antonii)、ヘロペルチス・テイボラ(Helopeltis theivora)、イセリア・プルカシ(Icerya purchasi)、イジオスコプス・ニチズルス(Idioscopus nitidulus)、ラオデルファクス・ストリアテルス(Laodelphax striatellus)、レプトコリサ・オラトリウス(Leptocorisa oratorius)、レプトコリサ・バリコルニス(Leptocorisa varicornis)、リグス・ヘスペルス(Lygus hesperus)、マコネリコックス・ヒルツスス(Maconellicoccus hirsutus)、マクロシフム・エウフォルビアエ(Macrosiphum euphorbiae)、マクロシフム・グラナリウム(Macrosiphum granarium)、マクロシフム・ロザエ(Macrosiphum rosae)、マクロステレス・クアドリリネアツス(Macrosteles quadrilineatus)、マハナルバ・フリムビオラタ(Mahanarva frimbiolata)、メガコプタ・クリブラリア(Megacopta cribraria)、メトポロフィウム・ジルホズム(Metopolophium dirhodum)、ミクチス・ロンギコルニス(Mictis longicornis)、ミズス・ペルシカエ(Myzus persicae)、ネフォテチックス・シンクチセプス(Nephotettix cincticeps)、ネウロコルプス・ロンギロストリス(Neurocolpus longirostris)、ネザラ・ビリヅラ(Nezara viridula)、ニラパルバタ・ルゲンス(Nilaparvata lugens)、パルラトリア・ペルガンジイ(Parlatoria pergandii)、パルラトリア・ジジフィ(Parlatoria ziziphi)、ペレグリヌス・マイジス(Peregrinus maidis)、フィロクセラ・ビチフォリアエ(Phylloxera vitifoliae)、フィソケルメス・ピセアエ(Physokermes piceae)、フィトコリス・カルフォルニクス(Phytocoris californicus)、フィトコリス・レラチブス(Phytocoris relativus)、ピエゾドルス・グイルジニイ(Piezodorus guildinii)、ポエシロカプスス・リネアツス(Poecilocapsus lineatus)、プサルス・バクシニコラ(Psallus vaccinicola)、シューダシスタ・ペルセアエ(Pseudacysta perseae)、シュードコックス・ブレビペス(Pseudococcus brevipes)、クアドラスピジオツス・ペルニシオスス(Quadraspidiotus perniciosus)、ロパロシフム・マイジス(Rhopalosiphum maidis)、ロパロシフム・パジ(Rhopalosiphum padi)、サイセチア・オレアエ(Saissetia oleae)、スカプトコリス・カスタネア(Scaptocoris castanea)、シザフィス・グラミヌム(Schizaphis graminum)、シトビオン・アベナエ(Sitobion avenae)、ソガテラ・フルシフェラ(Soga
tella furcifera)、トリアレウロデス・バポラリオルム(Trialeurodes vaporariorum)、トリアレウロデス・アブチロネウス(Trialeurodes abutiloneus)、ウナスピス・ヤノネンシス(Unaspis yanonensis)及びズリア・エントレリアナ(Zulia entrerriana)が含まれる。
(9) 膜翅目。特定の属の非網羅的なリストには、限定されないが、アクロミルメクス属種(Acromyrmex spp.)、アッタ属種(Atta spp)、カムポノツス属種(Camponotus spp.)、ジプリオン属種(Diprion spp.)、ドリコベスプラ属種(Dolichovespula spp.)、フォルミカ属種(Formica spp.)、モノモリウム属種(Monomorium spp.)、ネオジプリオン属種(Neodiprion spp.)、パラトレキナ属種(Paratrechina spp.)、フェイドレ属種(Pheidole spp.)、ポゴノミルメクス属種(Pogonomyrmex spp.)、ポリステス属種(Polistes spp.)、ソレノプシス属種(Solenopsis spp.)、テクノミルメクス属種(Technomyrmex,spp.)、テトラモリウム属種(Tetramorium spp.)、ベスプラ属種(Vespula spp.)、ベスパ属種(Vespa spp.)、及びキシロコパ属種(Xylocopa spp.)が含まれる。特定の種の非網羅的なリストには、限定されないが、アタリア・ロサエ(Athalia rosae)、アッタ・テクサナ(Atta texana)、カリロア・セラシ(Caliroa cerasi)、シムベクス・アメリカナ(Cimbex americana)、イリドミルメクス・フミリス(Iridomyrmex humilis)、リネピテマ・フミレ(Linepithema humile)、メリフェラ・スクテラタ(Mellifera Scutellata)、モノモリウム・ミニムム(Monomorium minimum)、モノモリウム・ファラオニス(Monomorium pharaonis)、ネオジプリオン・セルチフェル(Neodiprion
sertifer)、ソレノプシス・インビクタ(Solenopsis invicta)、ソレノプシス・ゲミナタ(Solenopsis geminata)、ソレノプシス・モレスタ(Solenopsis molesta)、ソレノプシス・リクテリ(Solenopsis richtery)、ソレノプシス・キシロニ(Solenopsis xyloni)、タピノマ・セッシレ(Tapinoma sessile)、及びワスマンニア・アウロプンクタタ(Wasmannia auropunctata)が含まれる。
(10) 等翅目。特定の属の非網羅的なリストには、限定されないが、コプトテルメス属種(Coptotermes spp.)、コルニテルメス属種(Cornitermes spp.)、クリプトテルメス属種(Cryptotermes spp.)、ヘテロテルメス属種(Heterotermes spp.)、カロテルメス属種(Kalotermes spp.)、インシシテルメス属種(Incisitermes spp.)、マクロテルメス属種(Macrotermes spp.)、マルギニテルメス属種(Marginitermes spp.)、ミクロセロテルメス属種(Microcerotermes spp.)、プロコルニテルメス属種(Procornitermes
spp.)、レチクリテルメス属種(Reticulitermes spp.)、スケドリノテルメス属種(Schedorhinotermes spp.)、及びズーテルモプシス属種(Zootermopsis spp.)が含まれる。特定の種の非網羅的なリストには、限定されないが、 コプトテルメス・アシナシフォルミス(Coptotermes acinaciformis)、コプトテルメス・クルビクナスス(Coptotermes
curvignathus)、コプトテルメス・フレンチ(Coptotermes frenchi)、コプトテルメス・フォルモサヌス(Coptotermes formosanus)、コプトテルメス・ゲストロイ(Coptotermes gestroi)、クリプトテルメス・ブレビス(Cryptotermes brevis)、ヘテロテルメス・アウレウス(Heterotermes aureus)、ヘテロテルメス・テヌイス(Heterotermes tenuis)、インシシテルメス・ミノル(Incisitermes minor)、インシシテルメス・スニデリ(Incisitermes snyderi)、ミクロテルメス・オベシ(Microtermes obesi)、ナスティテルメス・コルニガ(Nasutitermes corniger)、オドントテルメス・フォルモサヌス(Odontotermes formosanus)、オドントテルメス・オベスス(Odontotermes obesus)、レチクリテルメス・バニュレンシス(Reticulitermes banyulensis)、レチクリテルメス・グラッセイ(Reticulitermes grassei)、レチクリテルメス・フラビペス(Reticulitermes flavipes)、レチクリテルメス・ハゲニ(Reticulitermes hageni)、レチクリテルメス・ヘスペルス(Reticulitermes hesperus)、レチクリテルメス・サントネンシス(Reticulitermes santonensis)、レチクリテルメス・スペラツス(Reticulitermes speratus)、レチクリテルメス・チビアリス(Reticulitermes tibialis)、及びレチクリテルメス・ビルギニクス(Reticulitermes virginicus)が含まれる。
(11) 鱗翅目。特定の属の非網羅的なリストには、限定されないが、アドキソフィエ
ス属種(Adoxophyes spp.)、アグロチス属種(Agrotis spp.)、アルギロタエニア属種(Argyrotaenia spp.)、カコエキア属種(Cacoecia spp.)、カロプチリア属種(Caloptilia spp.)、キロ属種(Chilo spp.)、クリソデイキス属種(Chrysodeixis spp.)、コリアス属種(Colias spp.)、クラムバス属種(Crambus spp.)、ジアファニア属種(Diaphania spp.)、ジアトラエア属種(Diatraea spp.)、エアリアス属種(Earias spp.)、エフェスチア属種(Ephestia spp.)、エピメシス属種(Epimecis spp.)、フェルチア属種(Feltia spp.)、ゴルチナ属種(Gortyna spp.)、ヘリコベルパ属種(Helicoverpa
spp.)、ヘリオチス属種(Heliothis spp.)、インダルベラ属種(Indarbela spp.)、リトコレチス属種(Lithocolletis spp.)、ロキサグロチス属種(Loxagrotis spp.)、マラコソマ属種(Malacosoma spp.)、ネマポゴン属種(Nemapogon spp.)、ペリドローマ属種(Peridroma spp.)、フィロノリクテル属種(Phyllonorycter spp.)、プセウダレチア属種(Pseudaletia spp.)、プルテラ属種(Plutella spp.)、セサミア属種(Sesamia spp.)、スポドプテラ属種(Spodoptera spp.)、シナンテドン属種(Synanthedon spp.)、及びイポノメウタ属種(Yponomeuta spp.)が含まれる。特定の種の非網羅的なリストには、限定されないが、アカエア・ジャナタ(Achaea janata)、アドキソフィエス・オラナ(Adoxophyes orana)、アグロチス・イプシロン(Agrotis ipsilon)、アラバマ・アルギラセア(Alabama argillacea)、アモルビア・クネアナ(Amorbia cuneana)、アミエロイス・トランシテラ(Amyelois transitella)、アナカムプトデス・デフェクタリア(Anacamptodes defectaria)、アナルシア・リネアテラ(Anarsia lineatella)、アノミス・サブリフェラ(Anomis sabulifera)、アンチカルシア・ゲマタリス(Anticarsia gemmatalis)、アルキプス・アルギロスピラ(Archips argyrospila)、アルキプス・ロサナ(Archips rosana)、アルギロタエニア・シトラナ(Argyrotaenia citrana)、アウトグラファ・ガンマ(Autographa gamma)、ボナゴタ・クラナオデス(Bonagota
cranaodes)、ボルボ・シンナラ(Borbo cinnara)、ブックラトリクス・ツルベリエラ(Bucculatrix thurberiella)、カプア・レチクラナ(Capua reticulana)、カルポシナ・ニポネンシス(Carposina niponensis)、クルメチア・トランスベルサ(Chlumetia transversa)、コリストネウラ・ロサセアナ(Choristoneura rosaceana)、クナファロクロシス・メジナリス(Cnaphalocrocis medinalis)、コノポモルファ・クラメレラ(Conopomorpha cramerella)、コルシラ・セファロニカ(Corcyra cephalonica)、コッスス・コッスス(Cossus cossus)、シジア・カリアナ(Cydia caryana)、シジア・フネブラナ(Cydia funebrana)、シジア・モレスタ(Cydia molesta)、シジア・ニグリカナ(Cydia nigricana)、シジア・ポモネラ(Cydia pomonella)、ダルナ・ジズクタ(Darna diducta)、ジアファニア・ニチダリス(Diaphania nitidalis)、ジアトラエア・サッカラリス(Diatraea saccharalis)、ジアトラエア・グランジオセラ(Diatraea grandiosella)、エアリアス・インスラナ(Earias insulana)、エアリアス・ビッテラ(Earias vittella)、エクジトロファ・アウランチアヌム(Ecdytolopha aurantianum)、エラスモパルプス・リグネセルス(Elasmopalpus lignosellus)、エフェスチア・カウテラ(Ephestia cautella)、エフェスチア・エルテラ(Ephestia elutella)、エフェスチア・クエニエラ(Ephestia kuehniella)、エピノチア・アポレマ(Epinotia aporema)、エピフィアス・ポストビッタナ(Epiphyas postvittana)、エリオノタ・スラックス(Erionota thrax)、エスチグメネ・アクレア(Estigmene acrea)、エウポエシリア・アムビグエラ(Eupoecilia ambiguella)、エウクソア・アウキシリアリス(Euxoa auxiliaris)、ガレリア・メロネラ(Galleria mellonella)、グラフォリタ・モレスタ(Grapholita molesta)、ヘジレプタ・インジカタ(Hedylepta indicata)、ヘリコベルパ・アルミゲラ(Helicoverpa armigera)、ヘリコベルパ・ゼア(Helicoverpa zea)、ヘリオティス・ビレセンス(Heliothis virescens)、ヘルラ・ウンダリス(Hellula undalis)、ケイフェリア・リコペルシセラ(Keiferia lycopersicella)、レウシノデス・オルボナリス(Leucinodes orbonalis)、レウコプテラ・コフェラ(Leucoptera coffeella)、レウコプテラ・マリフォリエラ(Leucoptera malifoliella)、ロベシア・ボトラナ(Lobesia botrana)、ロキサグロチス・アルビコスタ(Loxagrotis albicosta)、リマントリア・ジスパル
(Lymantria dispar)、リオネチア・クレルケラ(Lyonetia clerkella)、マハセナ・コルベッチ(Mahasena corbetti)、マメストラ・ブラシカエ(Mamestra brassicae)、マンズカ・セクスタ(Manduca sexta)、マルカ・テスツラリス(Maruca testulalis)、メチサ・プラナ(Metisa plana)、ミチムナ・ウニプンクタ(Mythimna unipuncta)、ネオレウシノデス・エレガンタリス(Neoleucinodes elegantalis)、ニムフラ・デプンクタリス(Nymphula depunctalis)、オペロフテラ・ブルマタ(Operophtera brumata)、オストリニア・ヌビラリス(Ostrinia nubilalis)、オキシジア・ベスリア(Oxydia vesulia)、パンデミス・セラサナ(Pandemis cerasana)、パンデミス・ヘパラナ(Pandemis heparana)、パピリオ・デモドクス(Papilio demodocus)、ペクチノフォラ・ゴシピエラ(Pectinophora gossypiella)、ペリドロマ・サウシア(Peridroma saucia)、ペリレウコプテラ・コフェラ(Perileucoptera coffeella)、フトリマエア・オペルクレラ(Phthorimaea operculella)、フィロクニスチス・シトレラ(Phyllocnistis citrella)、フィロノリクテル・ブランカルデラ(Phyllonorycter blancardella)、ピエリス・ラパエ(Pieris rapae)、プラチペナ・スカブラ(Plathypena scabra)、プラチノタ・イダエウサリイス(Platynota idaeusalis)、プロジア・インテルプンクテラ(Plodia interpunctella)、プルテラ・キシロステラ(Plutella xylostella)、ポリクロシス・ビテアナ(Polychrosis viteana)、プライス・エンドカルパ(Prays endocarpa)、プライス・オレアエ(Prays oleae)、シューダレチア・ウニプンクタ(Pseudaletia unipuncta)、シュードプルシア・インクルデンス(Pseudoplusia includens)、ラキプルシア・ヌ(Rachiplusia nu)、シルポファガ・インセルツラス(Scirpophaga incertulas)、セサミア・インフェレンス(Sesamia inferens)、セサミア・ノナグリオイデス(Sesamia nonagrioides)、セトラ・ニテンス(Setora nitens)、シトトロガ・セレアレラ(Sitotroga cerealella)、スパルガノティス・ピレリアナ(Sparganothis pilleriana)、スポドプテラ・エクシグア(Spodoptera exigua)、スポドプテラ・フルギペルダ(Spodoptera frugiperda)、スポドプテラ・エリダニア(Spodoptera eridania)、テクラ・バシリデス(Thecla basilides)、チネア・ペリオネラ(Tinea pellionella)、チネオラ・ビセリエラ(Tineola bisselliella)、トリコプルシア・ニ(Trichoplusia ni)、ツタ・アブソルタ(Tuta absoluta)、ゼウゼラ・コフェアエ(Zeuzera coffeae)、及びゼウゼラ・ピリナ(Zeuzea pyrina)が含まれる。
(12) ハジラミ目。特定の属の非網羅的なリストには、限定されないが、アナチコラ属種(Anaticola spp.)、ボビコラ属種(Bovicola spp.)、ケロピステス属種(Chelopistes spp.)、ゴニオデス属種(Goniodes spp.)、メナカンツス属種(Menacanthus spp.)、及びトリコデクテス属種(Trichodectes spp.)が含まれる。特定の種の非網羅的なリストには、限定されないが、ボビコラ・ボビス(Bovicola bovis)、ボビコラ・カプラエ(Bovicola caprae)、ボビコラ・オビス(Bovicola ovis)、ケロピステス・メレアグリジス(Chelopistes meleagridis)、ゴニオデス・ディッシミリス(Goniodes dissimilis)、ゴニオデス・ギガス(Goniodes gigas)、メナカンツス・ストラミネウス(Menacanthus stramineus)、メノポン・ガリナエ(Menopon gallinae)、及びトリコデクテス・カニス(Trichodectes canis)が挙げられるが、これらに限定されない。
(13) 直翅目。特定の属の非網羅的なリストには、限定されないが、メラノプルス属種(Melanoplus spp.)、及びプテロフィラ属種(Pterophylla spp.)が含まれる。特定の種の非網羅的なリストには、限定されないが、アケタ・ドメスチクス(Acheta domesticus)、アナブルス・シンプレックス(Anabrus simplex)、グリロタルパ・アフリカーナ(Gryllotalpa africana)、グリロタルパ・アウストラリス(Gryllotalpa australis)、グリロタルパ・ブラキプテラ(Gryllotalpa brachyptera)、グリロタルパ・ヘキサダクチラ(Gryllotalpa hexadactyla)、ロクスタ・ミグラトリア(Locusta migratoria)、ミクロセントラム・レチネルベ(Microcentrum retinerve)、シストセルカ・グレガリア(Schistocerca gregaria)、及びスクデリア・フルカタ(Scudderia furcata)が含まれる。
(14) チャタテムシ目。特定の種の非網羅的なリストには、限定されないが、ホンチ
ャタテ(Liposcelis decolor)、カツブシチャタテ(Liposcelis entomophila)、カシヒメチャタテ(Lachesilla quercus)、及びコチャタテ(Trogium pulsatorium)が含まれる。
(15) ノミ目。特定の種の非網羅的なリストには、限定されないが、セラトフィルス・ガリナエ(Ceratophyllus gallinae)、セラトフィルス・ニゲル(Ceratophyllus niger)、クテノセファリデス・カニス(Ctenocephalides canis)、クテノセファリデス・フェリス(Ctenocephalides felis)、及びプレクス・イリタンス(Pulex irritans)が含まれる。
(16) 総翅目。特定の属の非網羅的なリストには、限定されないが、カリオトリプス属種(Caliothrips spp.)、フランクリニエラ属種(Frankliniella spp.)、スキルトトリプス属種(Scirtothrips spp.)、及びトリプス属種(Thrips spp.)が含まれる。特定の種の非網羅的なリストには、限定されないが、フランクリニエラ・ビスピノサ(Frankliniella bispinosa)、フランクリニエラ・フスカ(Frankliniella fusca)、フランクリニエラ・オクシデンタリス(Frankliniella occidentalis)、フランクリニエラ・シュルツゼイ(Frankliniella schultzei)、フランクリニエラ・トリチシ(Frankliniella tritici)、フランクリニエラ・ウイリアムジ(Frankliniella williamsi)、ヘリオトリプス・ハエモロイダリス(Heliothrips haemorrhoidalis)、リピホロトリプス・クルエンタツス(Rhipiphorothrips cruentatus)、スキルトトリプス・キトリ(Scirtothrips citri)、スキルトトリプス・ドーサリス(Scirtothrips dorsalis)、タエニオスリップス・ロパランテナリス(Taeniothrips rhopalantennalis)、トリプス・ハワイエンシス(Thrips hawaiiensis)、トリプス・ニグロピロスス(Thrips nigropilosus)、トリプス・オリエンタリス(Thrips orientalis)、トリプス・パルミ(Thrips palmi)、及びトリプス・タバシ(Thrips tabaci)が含まれる。
(17) シミ目。特定の属の非網羅的なリストには、限定されないが、レピスマ属種(Lepisma spp.)、及びテルモビア属種(Thermobia spp.)が含まれる。
(18) ダニ目。特定の属の非網羅的なリストには、限定されないが、アカルス属種(Acarus spp.)、アキュロプス属種(Aculops spp.)、アルグス属種(Argus spp.)、ブーフィラス属種(Boophilus spp.)、デモデクス属種(Demodex spp.)、デルマセントル属種(Dermacentor spp.)、エピトリメルス属種(Epitrimerus spp.)、エリオフィエス属種(Eriophyes spp.)、イクソデス属種(Ixodes spp.)、オリゴニクス属種(Oligonychus spp.)、パノニクス属種(Panonychus spp.)、リゾグリフス属種(Rhizoglyphus spp.)、及びテトラニクス属種(Tetranychus spp.)が含まれる。特定の種の非網羅的なリストには、限定されないが、アカラピス・ウォオジ(Acarapis woodi)、アカルス・シロ(Acarus siro)、アセリア・マンギフェラエ(Aceria mangiferae)、アクロプス・リコペルシシ(Aculops lycopersici)、アクルス・ペレカッシ(Aculus pelekassi)、アクルス・シュレクテンダリ(Aculus schlechtendali)、アムブリオマ・アメリカナム(Amblyomma americanum)、ブレビパルパス・オボバツス(Brevipalpus obovatus)、ブレビパルプス・ホエニシス(Brevipalpus phoenicis)、デルマセントル・バリアビリス(Dermacentor variabilis)、デルマトファゴイデス・プテロニッシヌス(Dermatophagoides pteronyssinus)、エオテトラニカス・カルピニ(Eotetranychus carpini)、リポニソイデス・サングイネウス(Liponyssoides sanguineus)、ノトエドレス・カチ(Notoedres cati)、オリゴニクス・コフェアエ(Oligonychus coffeae)、オリゴニクス・イリシス(Oligonychus ilicis)、オルニトニッスス・バコチ(Ornithonyssus bacoti)、パノニクス・シトリ(Panonychus citri)、パノニクス・ウルミ(Panonychus ulmi)、フィロコプトルタ・オレイボラ(Phyllocoptruta oleivora)、ポリファゴタルソネムス・ラツス(Polyphagotarsonemus latus)、リピセファルス・サングイネウス(Rhipicephalus
sanguineus)、サルコプテス・スカビエイ(Sarcoptes scabiei)、テゴロフス・ペルセアフロラエ(Tegolophus perseaflorae)、テトラニクス・ウルチカエ(Tetranychus urticae)、チロファグス・ロンギオール(Tyrophagus longior)、及びバロア・デストルクトル(Varroa destructor)が含まれる。
(19) クモ目。特定の属の非網羅的なリストには、限定されないが、ロクソスケレス属種(Loxosceles spp.)、ラトロデクツス属種(Latrodectus spp.)、及びアトラクス属種(Atrax spp.)が含まれる。特定の種の非網羅的なリストには、限定されないが、ロクソスケレス・レクルサ(Loxosceles reclusa)、ラトロデクツス・マクタンス(Latrodectus mactans)、及びアトラクス・ロブスツス(Atrax robustus)が含まれる。
(20) 結合綱。特定の種の非網羅的なリストには、限定されないが、スクチゲレラ・インマクラタ(Scutigerella immaculata)が含まれる。
(21) トビムシ亜綱。特定の種の非網羅的なリストには、限定されないが、キボシマルトビムシ(Bourletiella hortensis)、オニチウルス・アルマツス(Onychiurus armatus)、オニチウルス・フィメタリウス(Onychiurus fimetarius)、及びスミンツルス・ビリジス(Sminthurus viridis)が含まれる。
(22) 線形動物門。特定の属の非網羅的なリストには、限定されないが、アフェレンコイデス属種(Aphelenchoides spp.)、ベロノライムス属種(Belonolaimus spp.)、クリコネメラ属種(Criconemella spp.)、ジチレンクス属種(Ditylenchus spp.)、グロボデラ属種(Globodera spp.)、ヘテロデラ属種(Heterodera spp.)、ヒルシュマンニエラ属種(Hirschmanniella spp.)、ホプロライムス属種(Hoplolaimus spp.)、メロイドギネ属種(Meloidogyne spp.)、プラチレンクス属種(Pratylenchus spp.)、及びラドフォラス属種(Radopholus spp.)が含まれる。特定の種の非網羅的なリストには、限定されないが、ジロフィラリア・イミチス(Dirofilaria immitis)、グロボデラ・パリダ(Globodera pallida)、ヘテロデラ・グリシネス(Heterodera glycines)、ヘテロデラ・ゼアエ(Heterodera zeae)、メロイドギネ・インコグニタ(Meloidogyne incognita)、メロイドギネ・ジャバニカ(Meloidogyne javanica)、オンコセルカ・ボルブルス(Onchocerca volvulus)、プラチレンクス・ペネトランス(Pratylenchus penetrans)、ラドフォルス・シミリス(Radopholus similis)、及びロチレンクルス・レニフォルミス(Rotylenchulus reniformis)が含まれる。
(23) 軟体動物門。特定の種の非網羅的なリストには、限定されないが、アリオン・ブルガリス(Arion vulgaris)、ヒメリンゴマイマイ(Cornu aspersum)、ノハラナメクジ(Deroceras reticulatum)、リマックス・フラブス(Limax flavus)、ミラックス・ガガテス(Milax gagates)、及びポマセア・カナリキュラタ(Pomacea canaliculata)が含まれる。
防除に特に好ましい害虫群は、樹液を食する害虫である。樹液を食する害虫は、一般的に、注入口器及び/または吸引口器を有し、植物の樹液及び内部植物組織を餌にする。農業に特に懸念となる樹液を食する害虫の例として、アブラムシ、ヨコバイ、ガ、カイガラムシ、アザミウマ、キジラミ、コナカイガラムシ、カメムシ、及びコナジラミが挙げられるが、これらに限定されない。農業において注目すべき樹液を食する害虫を有する目の具体的な例として、シラミ目及び半翅目が挙げられるが、これらに限定されない。農業において注目すべき半翅目の具体例として、限定されないが、アウラカスピス属種(Aulacaspis spp.)、アフロフォラ属種(Aphrophora spp.)、アフィス属種(Aphis spp.)、ベミシア属種(Bemisia spp.)、コックス属種(Coccus spp.)、エウシスツス属種(Euschistus spp.)、リグス属種(Lygus spp.)、マクロシフム属種(Macrosiphum spp.)、ネザラ属種(Nezara spp.)、及びロパロシフム属種(Rhopalosiphum spp.)が挙げられる。
防除に特に好ましい他の害虫群は、咀嚼害虫である。咀嚼害虫は、一般的に、根、茎、葉、芽、及び生殖組織(花、果実、及び種子を含むが、これらに限定されない)を含む植物組織の咀嚼を可能にする口器を有する。農業に特に懸念となる咀嚼害虫の例として、毛虫、甲虫、バッタ、及びイナゴが挙げられるが、これらに限定されない。農業において注目すべき咀嚼害虫を有する目の具体的な例として、鞘翅目及び鱗翅目が挙げられるが、これらに限定されない。農業において注目すべき鞘翅目の具体例として、限定されないが、アントノムス属種(Anthonomus spp.)、セロトマ属種(Cerotoma spp.)、カエトクネマ属種(Chaetocnema spp.)、コラスピス属種(Colaspis spp.)、シクロセファラ属種(Cyclocephala spp.)、ジアブロチカ属種(Diabrotica spp.)、ヒペラ属種(Hypera spp.
)、フィロファガ属種( Phyllophaga spp.)、フィロトレタ属種(Phyllotreta spp.)、スフェノフォルス属種(Sphenophorus spp.)、シトフィルス属種(Sitophilus spp.)が挙げられる。
(A) R1は、H、F、Cl、Br、I、CN、NH2、NO2、(C1-C4)アルキル、(C3-C6)シクロアルキル、(C2-C4)アルケニル、(C3-C6)シクロアルケニル、(C2-C4)アルキニル、(C1-C4)アルコキシ、(C1-C4)ハロアルキル、(C3-C6)ハロシクロアルキル、(C2-C4)ハロアルケニル、(C3-C6)ハロシクロアルケニル、(C1-C4)ハロアルコキシ、S(C1-C4)アルキル、S(O)(C1-C4)アルキル、S(O)2(C1-C4)アルキル、S(C1-C4)ハロアルキル、S(O)(C1-C4)ハロアルキル、S(O)2(C1-C4)ハロアルキル、(C1-C4)アルキル-S(O)2NH2、及び(C1-C4)ハロアルキル-S(O)2NH2からなる群から選択され;
(B) R2は、H、F、Cl、Br、I、CN、NH2、NO2、(C1-C4)アルキル、(C3-C6)シクロアルキル、(C2-C4)アルケニル、(C3-C6)シクロアルケニル、(C2-C4)アルキニル、(C1-C4)アルコキシ、(C1-C4)ハロアルキル、(C3-C6)ハロシクロアルキル、(C2-C4)ハロアルケニル、(C3-C6)ハロシクロアルケニル、(C1-C4)ハロアルコキシ、S(C1-C4)アルキル、S(O)(C1-C4)アルキル、S(O)2(C1-C4)アルキル、S(C1-C4)ハロアルキル、S(O)(C1-C4)ハロアルキル、S(O)2(C1-C4)ハロアルキル、(C1-C4)アルキル-S(O)2NH2、及び(C1-C4)ハロアルキル-S(O)2NH2からなる群から選択され;
(C) R3は、H、F、Cl、Br、I、CN、NH2、NO2、(C1-C4)アルキル、(C3-C6)シクロアルキル、(C2-C4)アルケニル、(C3-C6)シクロアルケニル、(C2-C4)アルキニル、(C1-C4)アルコキシ、(C1-C4)ハロアルキル、(C3-C6)ハロシクロアルキル、(C2-C4)ハロアルケニル、(C3-C6)ハロシクロアルケニル、(C1-C4)ハロアルコキシ、S(C1-C4)アルキル、S(O)(C1-C4)アルキル、S(O)2(C1-C4)アルキル、S(C1-C4)ハロアルキル、S(O)(C1-C4)ハロアルキル、S(O)2
(C1-C4)ハロアルキル、(C1-C4)アルキル-S(O)2NH2、及び(C1-C4)ハロアルキル-S(O)2NH2からなる群から選択され;
(D) R4は、H、F、Cl、Br、I、CN、NH2、NO2、(C1-C4)アルキル、(C3-C6)シクロアルキル、(C2-C4)アルケニル、(C3-C6)シクロアルケニル、(C2-C4)アルキニル、(C1-C4)アルコキシ、(C1-C4)ハロアルキル、(C3-C6)ハロシクロアルキル、(C2-C4)ハロアルケニル、(C3-C6)ハロシクロアルケニル、(C1-C4)ハロアルコキシ、S(C1-C4)アルキル、S(O)(C1-C4)アルキル、S(O)2(C1-C4)アルキル、S(C1-C4)ハロアルキル、S(O)(C1-C4)ハロアルキル、S(O)2(C1-C4)ハロアルキル、(C1-C4)アルキル-S(O)2NH2、及び(C1-C4)ハロアルキル-S(O)2NH2からなる群から選択され;
(E) R5は、H、F、Cl、Br、I、CN、NH2、NO2、(C1-C4)アルキル、(C3-C6)シクロアルキル、(C2-C4)アルケニル、(C3-C6)シクロアルケニル、(C2-C4)アルキニル、(C1-C4)アルコキシ、(C1-C4)ハロアルキル、(C3-C6)ハロシクロアルキル、(C2-C4)ハロアルケニル、(C3-C6)ハロシクロアルケニル、(C1-C4)ハロアルコキシ、S(C1-C4)アルキル、S(O)(C1-C4)アルキル、S(O)2(C1-C4)アルキル、S(C1-C4)ハロアルキル、S(O)(C1-C4)ハロアルキル、S(O)2(C1-C4)ハロアルキル、(C1-C4)アルキル-S(O)2NH2、及び(C1-C4)ハロアルキル-S(O)2NH2からなる群から選択され;
(F) R6は、H及び(C1-C4)アルキルからなる群から選択され;
(G) R7は、H、F、Cl、Br、及びIからなる群から選択され;
(H) R8は、F、Cl、Br、及びIからなる群から選択され;
(I) R9は、H及び(C1-C4)アルキルからなる群から選択され;
(J) R10は、H、(C1-C4)アルキル、(C2-C4)アルケニル、(C1-C4)ハロアルキル、(C1-C4)アルキル(C1-C4)アルコキシ、C(=O)(C1-C4)アルキル、及び(C1-C4)アルコキシC(=O)(C1-C4)アルキルからなる群から選択され;
(K) R11は、H、F、Cl、Br、I、CN、NH2、NO2、(C1-C4)アルキル、(C3-C6)シクロアルキル、(C2-C4)アルケニル、(C3-C6)シクロアルケニル、(C2-C4)アルキニル、(C1-C4)アルコキシ、(C1-C4)ハロアルキル、(C3-C6)ハロシクロアルキル、(C2-C4)ハロアルケニル、(C3-C6)ハロシクロアルケニル、(C1-C4)ハロアルコキシ、S(C1-C4)アルキル、S(O)(C1-C4)アルキル、S(O)2(C1-C4)アルキル、S(C1-C4)ハロアルキル、S(O)(C1-C4)ハロアルキル、S(O)2(C1-C4)ハロアルキル、(C1-C4)アルキル-S(O)2NH2、及び(C1-C4)ハロアルキル-S(O)2NH2からなる群から選択され;
(L) R12は、H、F、Cl、Br、I、CN、NH2、NO2、(C1-C4)アルキル、(C3-C6)シクロアルキル、(C2-C4)アルケニル、(C3-C6)シクロアルケニル、(C2-C4)アルキニル、(C1-C4)アルコキシ、(C1-C4)ハロアルキル、(C3-C6)ハロシクロアルキル、(C2-C4)ハロアルケニル、(C3-C6)ハロシクロアルケニル、(C1-C4)ハロアルコキシ、S(C1-C4)アルキル、S(O)(C1-C4)アルキル、S(O)2(C1-C4)アルキル、S(C1-C4)ハロアルキル、S(O)(C1-C4)ハロアルキル、S(O)2(C1-C4)ハロアルキル、(C1-C4)アルキル-S(O)2NH2、及び(C1-C4)ハロアルキル-S(O)2NH2からなる群から選択され;
(M) R13は、H、F、Cl、Br、I、CN、NH2、NO2、(C1-C4)アルキル、(C3-C6)シクロアルキル、(C2-C4)アルケニル、(C3-C6)シクロアルケニル、(C2-C4)アルキニル、(C1-C4)アルコキシ、(C1-C4)ハロアルキル、(C3-C6)ハロシクロアルキル、(C2-C4)ハロアルケニル、(C3-C6)ハロシクロアルケニル、(C1-C4)ハロアルコキシ、S(C1-C4)アルキル、S(O)(C1-C4)アルキル、S(O)2(C1-C4)アルキル、S(C1-C4)ハロアルキル、S(O)(C1-C4)ハロアルキル、S(O)2(C1-C4)ハロアルキル、(C1-C4)アルキル-S(O)2NH2、及び(C1-C4)ハロアルキル-S(O)2NH2からなる群から選択され;
(N) R14は、H、F、Cl、Br、I、CN、NH2、NO2、(C1-C4)アルキル、(C3-C6)シクロアルキル、(C2-C4)アルケニル、(C3-C6)シクロアルケニル、(C2-C4)アルキニル、(C1-C4)アルコキシ、(C1-C4)ハロアルキル、(C3-C6)ハロシクロアルキル、(C2-C4)ハロアルケニル、(C3-C6)ハロシクロアルケニル、(C1-C4)ハロアルコキシ、S(C1-C4)アルキル、S(O)(C1-C4)アルキル、S(O)2(C1-C4)アルキル、S(C1-C4)ハロアルキル、S(O)(C1-C4)ハロアルキル、S(O)2(C1-C4)ハロアルキル、(C1-C4)アルキル-S(O)2NH2、及び(C1-C4)ハロアルキル-S(O)2NH
2からなる群から選択され;
(O) R15は、H、(C1-C4)アルキル、(C2-C4)アルケニル、(C1-C4)ハロアルキル、(C1-C4)アルキル(C1-C4)アルコキシ、C(=O)(C1-C4)アルキル、及び(C1-C4)アルコキシC(=O)(C1-C4)アルキルからなる群から選択され;
(P) R16は、(C3-C8)シクロアルキル、アゼチジニル、2,5-ジオキソイミダゾリジニル、2,4-ジオキソ-1,3-ジアザスピロ[4.4]ノナニルイソオキサゾリジノニル、イミダゾリジノニル、イソオキサゾリジノニル、モルホリニル、オキサゾリジノニル、オキセタニル、ピペラジニル、ピペリジニル、ピラニル、ピロリジニル、ピロリジノニル、テトラヒドロフラニル、テトラヒドロピラニル、テトラヒドロチオフェニル、テトラヒドロチオフェニル-オキシド、テトラヒドロチオフェニル-ジオキシド、チエタニル、チエタニル-オキシド、チエタニル-ジオキシド、及びチオキソチアゾリジノニルからなる群から選択され、シクロアルキル、アゼチジニル、2,5-ジオキソイミダゾリジニル、2,4-ジオキソ-1,3-ジアザスピロ[4.4]ノナニルイソオキサゾリジノニル、イミダゾリジノニル、イソオキサゾリジノニル、モルホリニル、オキサゾリジノニル、オキセタニル、ピペラジニル、ピペリジニル、ピラニル、ピロリジニル、ピロリジノニル、テトラヒドロフラニル、テトラヒドロピラニル、テトラヒドロチオフェニル、テトラヒドロチオフェニル-オキシド、テトラヒドロチオフェニル-ジオキシド、チエタニル、チエタニル-オキシド、チエタニル-ジオキシド、及びチオキソチアゾリジノニルの各基は、H、F、Cl、Br、I、CN、NH2、NO2、オキソ、(C1-C4)アルキル、(C1-C4)ハロアルキル、C(=O)O(C1-C4)アルキル、(C=O)NH(C1-C4)アルキル、(C=O)NH(C1-C4)ハロアルキル、C(=O)(C3-C6)シクロプロピル、C(=O)(C1-C4)ハロアルキル、C(=O)(C1-C4)アルキル(C1-C4)アルコキシ、及び(C1-C4)アルキル-モルホリニルから選択される1つ以上の置換基で任意選択的に置換されてもよく;
(Q) Q1及びQ2は、それぞれ独立にO及びSからなる群から選択される);ならびに
式1の分子のN-オキシド、農学的に許容可能な酸付加塩、塩誘導体、溶媒和物、エステル誘導体、結晶多形体、同位体、分割立体異性体、及び互変異性体。
シクロプロピル、シクロブチル、シクロペンチル、シクロヘキシル、アゼチジニル、モルホリニル、オキセタニル、ピラニル、テトラヒドロチオフェニル、チエタニル、チエタニル-オキシド、及びチエタニル-ジオキシドの各基は、H、F、CN、C(=O)OC(CH3)3、及びC(=O)CF3からなる群から選択される1つ以上の置換基で任意選択的に置換されてもよい。この実施形態は、R1、R2、R3、R4、R5、R6、R7、R8、R9、R10、R11、R12、R13、R14、R15、Q1、及びQ2のその他の実施形態と組み合わせて用いられてもよい。
(A) R1が、H、F、及びClからなる群から選択され;
(B) R2が、H、F、Cl、Br、(C1-C4)アルキル、及び(C1-C4)ハロアルキルからなる群から選択され;
(C) R3が、H、F、Cl、(C1-C4)アルキル、(C1-C4)ハロアルキル、及び(C1-C4)ハロアルコキシからなる群から選択され;
(D) R4が、H、F、Cl、Br、(C1-C4)アルキル、及び(C1-C4)ハロアルキルからなる群から選択され;
(E) R5がHであり;
(F) R6がHであり;
(G) R7が、Cl及びBrからなる群から選択され;
(H) R8が、Cl及びBrからなる群から選択され;
(I) R9がHであり;
(J) R10がHであり;
(K) R11がHであり;
(L) R12がHであり;
(M) R13が、H、Cl、及び(C1-C4)ハロアルキルからなる群から選択され;
(N) R14がHであり;
(O) R15が、H及び(C1-C4)アルキルからなる群から選択され;
(P) R16が、(C3-C8)シクロアルキル、アゼチジニル、モルホリニル、オキセタニル、ピラニル、テトラヒドロチオフェニル、チエタニル、チエタニル-オキシド、及びチエタニル-ジオキシドからなる群から選択され、シクロアルキル、アゼチジニル、モルホリニル、オキセタニル、ピラニル、テトラヒドロチオフェニル、チエタニル、チエタニル-オキシド、及びチエタニル-ジオキシドの各基が、H、F、CN、C(=O)O(C1-C4)アルキル、C(=O)(C3-C6)シクロプロピル、C(=O)(C1-C4)ハロアルキル、及びC(=O)(C1-C4)アルキル(C1-C4)アルコキシからなる群から選択される1つ以上の置換基で任意選択的に置換されてもよく;
(Q) Q1及びQ2がOである。
(A) R1が、H及びClからなる群から選択され;
(B) R2が、H、Cl、Br、CH3、及びCF3からなる群から選択され;
(C) R3が、H、F、Cl、CH3、及びCF3、OCF3からなる群から選択され;
(D) R4が、H、F、Cl、Br、CH3、及びCF3からなる群から選択され;
(E) R5がHであり;
(F) R6がHであり;
(G) R7が、Cl及びBrからなる群から選択され;
(H) R8が、Cl及びBrからなる群から選択され;
(I) R9がHであり;
(J) R10がHであり;
(K) R11がHであり;
(L) R12がHであり;
(M) R13が、H、Cl、及びCF3からなる群から選択され;
(N) R14がHであり;
(O) R15が、H及びCH3からなる群から選択され;
(P) R16が、(C3-C8)シクロアルキル、アゼチジニル、モルホリニル、オキセタニル、ピラニル、テトラヒドロチオフェニル、チエタニル、チエタニル-オキシド、及びチエタニル-ジオキシドからなる群から選択され、シクロアルキル、アゼチジニル、モルホリニル、オキセタニル、ピラニル、テトラヒドロチオフェニル、チエタニル、チエタニル-オキシド、及びチエタニル-ジオキシドの各基が、H、F、CN、C(=O)O(C1-C4)アルキル、C(=O)(C3-C6)シクロプロピル、C(=O)(C1-C4)ハロアルキル、及びC(=O)(C1-C4)アルキル(C1-C4)アルコキシからなる群から選択される1つ以上の置換基で任意選択的に置換されてもよく;
(Q) Q1及びQ2がOである。
スチルベン類1-1(R1、R2、R3、R4、R5、R6、及びR9は前記に開示したとおりである)を、クロロホルムまたはブロモホルムなどのカルベン源とN-ベンジル-N,N-ジエチルエタンアミニウムクロリドなどの相間移動触媒との存在下、水などの極性プロトン性溶媒中にて約0℃〜約40℃の温度で水酸化ナトリウムなどの塩基で処理して、ジアリールシクロプロパン類1-2(R1、R2、R3、R4、R5、R6、R7、R8、及びR9は前記に開示したとおりである)を得ることができる(スキーム1、ステップa)。ジアリールシクロプロパン類1-2を、過ヨウ素酸ナトリウムなどの化学量論的な酸化剤の存在下、溶媒混合液(好ましくは水、酢酸エチル、及びアセトニトリル)中にて約0℃〜約40℃の温度で塩化ルテニウム(III)などの遷移金属で処理することで、シクロプロピルカルボン酸類1-3(R1、R2、R3、R4、R5、R6、R7、R8、及びR9は前記に開示したとおりである)を得ることができる(スキーム1、ステップb)。
スキーム1
て、中間体の第1アルコール1.5-3(R1、R2、R3、R4、R5、及びR6は上記に定義したとおりであり、R9は前記に開示したとおりである)を得ることができる(スキーム 1.5、ステップb)。後に続く化学的変化を正常に完了するために第1アルコール1.5-3の保護が必要となり、種々の保護基戦略が利用され得る。例えば、アルコール1.5-3を、触媒量のパラ-トルエンスルホン酸一水和物などの有機酸の存在下、ジエチルエーテルなどの非プロトン性溶媒中にて約0℃〜およそ外界温度で3,4-ジヒドロ-2-H-ピランで処理することで、テトラヒドロ-2-H-ピラン(THP)保護アルコール1.5-4(R1、R2、R3、R4、R5、R6、及びR9は上記に定義したとおりである)が得られる(スキーム1.5、ステップc)。THP保護スチリル中間体を、水酸化ナトリウムまたは水酸化カリウムなどの塩基とテトラブチルアンモニウムヘキサフルオロホスフェートなどの触媒との存在下、約25℃〜約45℃の温度でクロロホルムなどのカルベン源で処理することによって、THP保護シクロプロパン中間体1.5-5(R1、R2、R3、R4、R5、R6、及びR9は上記に定義したとおりであり、R7及びR8は前記に開示したとおりである)に転化することができる(スキーム1.5、ステップd)。THP保護シクロプロパン中間体1.5-5(R1、R2、R3、R4、R5、R6、R7、R8、及びR9は上記に定義したとおりである)の脱保護は、メタノールなどの極性プロトン性溶媒中にて約22℃の温度で触媒量のパラ-トルエンスルホン酸一水和物などの有機酸で処理することで達成されて、シクロプロピルメタノール中間体1.5-6を得ることができる(スキーム1.5、ステップe)。第1アルコール中間体1.5-6(R1、R2、R3、R4、R5、R6、R7、R8、及びR9は上記に定義したとおりである)の酸化は、当該技術で既知の種々の試薬及び条件を用いて達成でき(Figadere, B.及びFranck, X.,「Carboxylic Acids: Synthesis from Alcohols」Science of Synthesis2006, (20a) pp 173 - 204)、それらの多くが特異な官能基の相溶性及び選択性を提供する。例えば、アルコール中間体1.5-6を、希硫酸及びアセトン溶液中の三酸化クロムの溶液であるジョーンズ試薬により処理することで、シクロプロピルカルボン酸1-3(R1、R2、R3、R4、R5、R6、R7、R8、及びR9は上記に定義したとおりである)が得られる(スキーム1.5、ステップf)。
スキーム1.5
スチルベン類1-1は、スキーム2で概説するいくつかの異なる方法で調製され得る。フェニルカルボニル類2-1(R1、R2、R3、R4、R5、及びR6は前記に開示したとおりである)を、ナトリウムメトキシドなどの塩基の存在下、N,N-ジメチルホルムアミドなどの極性非プロトン性溶媒中にて約-10℃〜約30℃の温度でアルコキシベンジルホスホネート類2-2で処理し、続いて40℃〜約80℃に加熱して、スチルベン類1-1を得ることができる(スキーム2、ステップa)。
スキーム2
さらに別の実施形態では、スチルベン類1-1は、スキーム2.5で概説するウィッティヒオレフィン化方法(Chalal, M.; Vervandier-Fasseur, D.; Meunier, P.; Cattey, H.; Hierso, J.-C. Tetrahedron 2012, 68, 3899-3907)によっても調製され得る。フェニルカルボニル類2-1(R1、R2、R3、R4、及びR5は前記に開示したとおりであり、R6はHである)を、n-ブチルリチウムなどの塩基の存在下、テトラヒドロフランなどの極性非プロトン性溶媒中にて約-78℃〜外界温度でアルコキシベンジルトリフェニルホスホニウムクロリド類2.5-2で処理して、スチルベン類1-1を得ることができる(スキーム2.5、ステップa)。
スキーム2.5
シクロプロピルアミド類3-3(R1、R2、R3、R4、R5、R6、R7、R8、R9、R10、R11、R12、R13、R14、Q2、R15、及びR16は前記に開示したとおりである)は、ジクロロメタン、テトラヒドロフラン、1,2-ジクロロエタン、ジメチルホルムアミド、またはこれらの任意の組み合わせなどの無水非プロトン性溶媒中にて約0℃〜約120℃の温度で、アミン類またはアミン塩類3-2(R10、R11、R12、R13、R14、Q2、ならびにR15及びR16は前記に開示したとおりである)と、活性カルボン酸類3-1(Aは活性化基であり、R1、R2、R3、R4、R5、R6、R7、R8、及びR9は前記に開示したとおりである)と共に、トリエチルアミン、ジイソプロピルエチルアミン、4-メチルモルホリン、または4-ジメチルアミノピリジンなどの塩基によって処理することで調製され得る(スキーム3、ステップa)。
活性カルボン酸類3-1は、酸塩化物、酸臭化物、もしくは酸フッ化物などの酸ハロゲン化物;パラ-ニトロフェニルエステル、ペンタフルオロフェニルエステル、エチル(ヒドロキシイミニオ)シアノ酢酸エステル、メチルエステル、エチルエステル、ベンジルエステル、N-ヒドロキシスクシンイミジルエステル、ヒドロキシベンゾトリアゾール-1-イルエステル、もしくはヒドロキシピリジルトリアゾール-1-イルエステルなどのカルボン酸エステル;O-アシルイソ尿素;酸無水物;またはチオエステルであってもよい。酸塩化物類は、塩化オキサリルまたは塩化チオニルなどの脱水塩素化試薬により処理することで、対応するカルボン酸類から調製され得る。活性カルボン酸エステル類3-1は、in situで、1-[ビス(ジメチルアミノ)メチレン]-1H-1,2,3-トリアゾロ[4,5-b]ピリジニウム3-オキシドヘキサフルオロホスフェート(HATU)、O-(ベンゾトリアゾール-1-イル)-N,N,N′,N′-テトラメチルウロニウムヘキサフルオロホスフェート(HBTU)、または(1-シアノ-2-エトキシ-2-オキソエチリデンアミノオキシ)ジメチルアミノ-モルホリノ-カルベニウムヘキサフルオロホスフェート(COMU)などのウロニウム塩を用いてカルボン酸類から調製され得る。また、活性カルボン酸エステル類3-1は、in situで、ベンゾトリアゾール-1-イル-オキシトリピロリジノホスホニウムヘキサフルオロホスフェート(PyBop)などのホスホニウム塩を用いてカルボン酸類から調製され得る。さらに、活性カルボン酸エステル類3-1は、in situで、ヒドロキシベンゾトリアゾール・一水和物(HOBt)または1-ヒドロキシ-7-アザベンゾトリアゾール(HOAt)などのトリアゾールの存在下、1-(3-ジメチルアミノプロピル)-3-エチルカルボジイミド、またはジシクロヘキシルカルボジイミドなどのカップリング試薬を用いてカルボン酸類から調製され得る。O-アシルイソ尿素類は、1-(3-ジメチルアミノプロピル)-3-エチルカルボジイミドまたはジシクロヘキシルカルボジイミドなどの脱水カルボジイミドを用いて調製され得る。また、活性カルボン酸エステル類3-1
は、in situで、1-ヒドロキシ-7-アザベンゾトリアゾール(HOAt)などのトリアゾールの存在下、2-クロロ-1,3-ジメチルイミダゾリジニウムヘキサフルオロホスフェート(CIP)などのカップリング試薬を用いてカルボン酸類から調製され得る。さらに、活性カルボン酸エステル類3-1は、in situで、ピリジンなどの塩基の存在下、2,4,6-トリプロピル-1,3,5,2,4,6-トリオキサトリホスフィナン2,4,6-トリオキシド(T3P(登録商標))などのカップリング試薬を用いてカルボン酸類から調製され得る。
シクロプロピルアミド類3-3(R16はチエタニルまたはテトラヒドロチオフェニルであり、R15は前記に開示したとおりである)は、ジクロロメタンなどの極性非プロトン性溶媒中の約1当量のメタ-クロロ過安息香酸(スルホキシド)、または約2当量のメタ-クロロ過安息香酸(スルホン)を用いて約0℃〜約40℃の温度で処理することで、対応するスルホキシドまたはスルホンに酸化され得る。あるいは、シクロプロピルアミド類3-3(R16はチエタニルまたはテトラヒドロチオフェニルであり、R15は前記に開示したとおりである)は、酢酸などのプロトン性溶媒中の1当量の過ホウ酸ナトリウム(スルホキシド)、または2当量の過ホウ酸ナトリウム(スルホン)を用いて処理することで、対応するスルホキシドまたはスルホンに酸化され得る。この酸化は、約40℃〜約100℃の温度で、約1.5当量の過ホウ酸ナトリウムを用いて行われて、クロマトグラフィで分離可能なスルホキシドシクロプロピルアミド類とスルホンシクロプロピルアミド類との混合物3-3を得ることができる。
シクロプロピルアミド類3-3(R3はNO2である)は、塩化アンモニウムなどの酸供与源と、メタノール、水、またはこれらの混合物などのプロトン性溶媒中の鉄と共に、約20℃〜約60℃の温度で処理することで、対応するNH2に還元され得る。
スキーム3
ルアミン、4-メチルモルホリン、または4-ジメチルアミノピリジンなどの塩基によって処理することで調製され得る(スキーム4、ステップa)。
活性カルボン酸類4-1は、酸塩化物、酸臭化物、もしくは酸フッ化物などの酸ハロゲン化物;パラ-ニトロフェニルエステル、ペンタフルオロフェニルエステル、エチル(ヒドロキシイミニオ)シアノ酢酸エステル、メチルエステル、エチルエステル、ベンジルエステル、N-ヒドロキシスクシンイミジルエステル、ヒドロキシベンゾトリアゾール-1-イルエステル、もしくはヒドロキシピリジルトリアゾール-1-イルエステルなどのカルボン酸エステル;O-アシルイソ尿素;酸無水物;またはチオエステルであってもよい。酸塩化物類は、塩化オキサリルまたは塩化チオニルなどの脱水塩素化試薬により処理することで、対応するカルボン酸類から調製され得る。活性カルボン酸エステル類4-1は、in situで、1-[ビス(ジメチルアミノ)メチレン]-1H-1,2,3-トリアゾロ[4,5-b]ピリジニウム3-オキシドヘキサフルオロホスフェート(HATU)、O-(ベンゾトリアゾール-1-イル)-N,N,N′,N′-テトラメチルウロニウムヘキサフルオロホスフェート(HBTU)、または(1-シアノ-2-エトキシ-2-オキソエチリデンアミノオキシ)ジメチルアミノ-モルホリノ-カルベニウムヘキサフルオロホスフェート(COMU)などのウロニウム塩を用いてカルボン酸類から調製され得る。また、活性カルボン酸エステル類4-1は、in situで、ベンゾトリアゾール-1-イル-オキシトリピロリジノホスホニウムヘキサフルオロホスフェート(PyBop)などのホスホニウム塩を用いてカルボン酸類から調製され得る。さらに、活性カルボン酸エステル類4-1は、in situで、ヒドロキシベンゾトリアゾール・一水和物(HOBt)または1-ヒドロキシ-7-アザベンゾトリアゾール(HOAt)などのトリアゾールの存在下、1-(3-ジメチルアミノプロピル)-3-エチルカルボジイミド、またはジシクロヘキシルカルボジイミドなどのカップリング試薬を用いてカルボン酸類から調製され得る。O-アシルイソ尿素類は、1-(3-ジメチルアミノプロピル)-3-エチルカルボジイミドまたはジシクロヘキシルカルボジイミドなどの脱水カルボジイミドを用いて調製され得る。また、活性カルボン酸エステル類4-1は、in situで、1-ヒドロキシ-7-アザベンゾトリアゾール(HOAt)などのトリアゾールの存在下、2-クロロ-1,3-ジメチルイミダゾリジニウムヘキサフルオロホスフェート(CIP)などのカップリング試薬を用いてカルボン酸類から調製され得る。さらに、活性カルボン酸エステル類4-1は、in situで、ピリジンなどの塩基の存在下、2,4,6-トリプロピル-1,3,5,2,4,6-トリオキサトリホスフィナン2,4,6-トリオキシド(T3P(登録商標))などのカップリング試薬を用いてカルボン酸類から調製され得る。
スキーム4
活性カルボン酸類5-2は、酸塩化物、酸臭化物、もしくは酸フッ化物などの酸ハロゲン化物;パラ-ニトロフェニルエステル、ペンタフルオロフェニルエステル、エチル(ヒドロキシイミニオ)シアノ酢酸エステル、メチルエステル、エチルエステル、ベンジルエステル、N-ヒドロキシスクシンイミジルエステル、ヒドロキシベンゾトリアゾール-1-イルエステル、もしくはヒドロキシピリジルトリアゾール-1-イルエステルなどのカルボン酸エステル;O-アシルイソ尿素;酸無水物;またはチオエステルであってもよい。酸塩化物類は、塩化オキサリルまたは塩化チオニルなどの脱水塩素化試薬により処理することで、対応するカルボン酸類から調製され得る。活性カルボン酸エステル類5-2は、in situで、1-[ビス(ジメチルアミノ)メチレン]-1H-1,2,3-トリアゾロ[4,5-b]ピリジニウム3-オキシドヘキサフルオロホスフェート(HATU)、O-(ベンゾトリアゾール-1-イル)-N,N,N',N'-テトラメチルウロニウムヘキサフルオロホスフェート(HBTU)、または(1-シアノ-2-エトキシ-2-オキソエチリデンアミノオキシ)ジメチルアミノ-モルホリノ-カルベニウムヘキサフルオロホスフェート(COMU)などのウロニウム塩を用いてカルボン酸類から調製され得る。また、活性カルボン酸エステル類5-2は、in situで、ベンゾトリアゾール-1-イル-オキシトリピロリジノホスホニウムヘキサフルオロホスフェート(PyBop)などのホスホニウム塩を用いてカルボン酸類から調製され得る。さらに、活性カルボン酸エステル類5-2は、in situで、ヒドロキシベンゾトリアゾール・一水和物(HOBt)または1-ヒドロキシ-7-アザベンゾトリアゾール(HOAt)などのトリアゾールの存在下、1-(3-ジメチルアミノプロピル)-3-エチルカルボジイミド、またはジシクロヘキシルカルボジイミドなどのカップリング試薬を用いてカルボン酸類から調製され得る。O-アシルイソ尿素類は、1-(3-ジメチルアミノプロピル)-3-エチルカルボジイミドまたはジシクロヘキシルカルボジイミドなどの脱水カルボジイミドを用いて調製され得る。また、活性カルボン酸エステル類5-2は、in situで、1-ヒドロキシ-7-アザベンゾトリアゾール(HOAt)などのトリアゾールの存在下、2-クロロ-1,3-ジメチルイミダゾリジニウムヘキサフルオロホスフェート(CIP)などのカップリング試薬を用いてカルボン酸類から調製され得る。さらに、活性カルボン酸エステル類5-2は、in situで、ピリジンなどの塩基の存在下、2,4,6-トリプロピル-1,3,5,2,4,6-トリオキサトリホスフィナン2,4,6-トリオキシド(T3P(登録商標))などのカップリング試薬を用いてカルボン酸類から調製され得る。
スキーム5
スキーム6
ホルムアミド、ジメチルスルホキシド、酢酸エチル、テトラヒドロフラン、及び1,4-ジオキサンからなる群から選択される極性非プロトン性溶媒中におけるピニック酸化(Pinnick oxidation)条件下、約0℃〜およそ外界温度で、アルデヒド7-4を酸化させることによって得ることができる(スキーム7、ステップd)。本反応を行う際に発熱が生じる可能性があるため、標準的な安全上の措置を講じるべきである。
スキーム7
スキーム8
市販原料から得られた出発物質、試薬、溶媒は、さらさる精製をせずに使用した。無水溶媒はAldrich社製のSure/Seal(商標)として購入し、そのまま使用した。融点は、トーマスフーバーユニメルト(Thomas Hoover Unimelt)キャピラリ融点装置またはスタンフォードリサーチシステムズ(Stanford Research Systems)社製のOptiMelt自動融点システムで取得し、未補正である。「室温」を用いる実施例は、約20℃〜約24℃の範囲の温度で空調制御された実験室で実施された。分子には、ISIS Draw、ChemDraw、またはACD Name Pro内の命名プログラムに従って命名された既知の名称を付与している。こうしたプログラムが分子に命名できない場合、従来の命名則を用いてかかる分子を称している。特記しない限り、1H NMRスペクトルデータはppm(δ)単位であり、300 MHz、400 MHz、500 MHz、または600 MHzで記録され;13C NMRスペクトルデータはppm(δ)単位であり、75 MHz、100 MHz、または150 MHzで記録され;19F NMRスペクトルデータはppm(δ)単位であり、376 MHzで記録された。
ジクロロ-3-(4-メトキシフェニル)シクロプロピル)ベンゼン(C22)(2.8 g、7.7 mmol)と過ヨウ素酸ナトリウム(33 g、160 mmol)との水:酢酸エチル:アセトニトリル(8:1:1、155 mL)攪拌混合液に23℃で加えた。得られた二相の褐色の混合物を23℃で5時間強力に攪拌した。反応混合物を水(1000 mL)で希釈し、ジクロロメタン(4×200 mL)で抽出した。混合有機層を硫酸マグネシウムで乾燥し、濾過及び濃縮した。残渣を水酸化ナトリウム溶液(1 M、100 mL)で希釈し、ジエチルエーテル(4×50 mL)で洗浄した。水層を濃塩酸を用いてpH 2に調整し、ジクロロメタン(3×50 mL)で抽出した。混合有機層を硫酸マグネシウムで乾燥し、濾過及び濃縮して、表題生成物を淡褐色の粉末(0.78 g、34%)として得た:融点117℃〜120℃;1H NMR(400 MHz, DMSO-d6)δ 13.38 (br s, 1H), 7.52 - 7.65 (m, 3H), 3.57 (d, J = 8.5 Hz, 1H), 3.50 (d, J = 8.5 Hz, 1H);IR (薄膜) 3083 (s), 3011 (s), 1731 (s), 1590 (w), 1566 (s), 1448 (w), 1431 (m), 1416 (m)
cm-1。
トランス-2,2-ジクロロ-3-(3,4,5-トリクロロフェニル)シクロプロパンカルボン酸(C2)
m/z333 ([M-H]-)。
171.52, 132.91, 132.76, 132.29, 130.66, 130.62, 128.02, 61.48, 39.65, 37.13;ESIMS m/z 298 ([M-H]-)。
トランス-2,2-ジクロロ-3-(3-(トリフルオロメチル)フェニル)シクロプロパン
カルボン酸(C5)
(400 MHz, DMSO-d6) δ 13.44 (brs, 1H), 8.01 (s, 1H), 7.82 (s, 1H), 3.52 (d, J =
8.2 Hz, 1H), 3.29 (d, J = 8.2 Hz, 1H);ESIMS m/z 333 ([M-H]-)。
Hz, 2H), 3.57 - 3.53 (m, 1H), 3.51 - 3.47 (m, 1H);ESIMS m/z 387 ([M-H]-)。
3.69 - 3.60 (m, 2H);ESIMS m/z 333 ([M-H]-)。
δ 13.37 (brs, 1H), 7.76 (s, 3H), 3.57 (d, J = 8.8 Hz, 1H), 3.48 (d, J = 8.8 Hz, 1H);ESIMS m/z 377 ([M-H]-)。
1H), 7.37 (d, J = 9.8 Hz, 1H), 3.52 (q, J = 8.5 Hz, 2H);ESIMS m/z 281 ([M-H]-)。
(400MHz, DMSO-d6) δ 13.40 (brs, 1H), 7.59 (m, 1H), 7.55 (d, J = 8.4 Hz, 1H), 7.33 (dd, J = 2.0, 8.4 Hz, 1H), 3.55 - 3.38 (m, 2H);ESIMS m/z 281 ([M-H]-)。
(400 MHz, CDCl3) δ 7.16 (d, J = 8.4 Hz, 2H), 6.88 (d, J = 8.31 Hz, 2H), 4.03 (q, J = 6.8 Hz, 2H), 3.41 (d, J = 8.0 Hz, 1H), 2.81 (d, J = 8.0 Hz, 1H), 1.41 (t,
J = 6.8 Hz, 3H);ESIMS m/z 273 ([M-H]-)。
トランス-1,2,3-トリクロロ-5-(2,2-ジクロロ-3-(4-メトキシフェニル)シクロプロピル)ベンゼン(C23)
J = 0.6 Hz, 2H), 7.29 - 7.22 (m, 2H), 6.96 - 6.89 (m, 2H), 3.83 (s, 3H), 3.12 (d, J = 8.8 Hz, 1H), 3.06 (d, J = 8.7 Hz, 1H);13C NMR (101 MHz, CDCl3) δ 159.46, 135.08, 134.23, 130.91, 129.85, 129.16, 125.42, 114.02, 64.67, 55.32, 39.62, 38.48。
, 1H), 6.96 - 6.90 (m, 2H), 3.83 (s, 3H), 3.11 (app. q, J= 8.8 Hz, 2H);13C NMR (101 MHz, CDCl3) δ 159.39, 134.90, 132.62, 131.99, 130.90, 130.40, 129.90, 128.33, 125.81, 113.98, 64.94, 55.33, 39.52, 38.75。
2H), 6.94 (d, J = 8.4 Hz, 2H), 3.83 (s, 3H), 3.19 (s, 2H);ESIMS m/z361 ([M+H]+)。
トランス-1-(2,2-ジクロロ-3-(4-メトキシフェニル)シクロプロピル)-3-(トリフルオロメチル)ベンゼン(C26)
(m, 4H), 7.29 (d, J = 9.0 Hz, 2H), 6.94 (d, J = 9.0 Hz, 2H), 7.35 - 7.25 (m, 3H), 7.97 - 6.88 (m, 1H), 3.83 (s, 3H), 3.19 (m, 2H);ESIMS m/z 361 ([M+H]+)。
7.57 (d, J = 2.0 Hz, 1H), 7.44 (d, J = 8.8 Hz, 1H), 7.35 - 7.25 (m, 3H), 7.97 -
6.88 (m, 1H), 3.84 (s, 3H), 3.15 - 3.05 (m, 2H);ESIMS m/z 411 ([M+H]+)。
), 7.45 (s, 2H), 7.25 (d, J = 9.0 Hz, 2H), 6.92 (d, J = 9.0 Hz, 1H), 3.83 (s, 3H), 3.15 - 3.05 (m, 2H);ESIMS m/z 453 ([M+H]+)。
7.36 (d, J = 9.0 Hz, 2H), 7.20 (s, 2H), 6.93 (d, J = 9.0 Hz, 2H), 3.83 (s, 3H),
3.15 - 3.05 (m, 2H);ESIMS m/z 439 ([M+H]+)。
ル)ベンゼン(C34)
7.49 (s, 1H), 7.30 (s, 1H), 7.28 - 7.24 (m, 3H), 6.92 (d, J = 8.0 Hz, 2H), 3.92
(s, 3H), 3.01 (q, J = 8.8 Hz, 2H);ESIMS m/z 405 ([M+H]+)。
7.27 (d, J = 8.8 Hz, 2H), 7.14 (s, 2H), 7.06 (s, 1H), 6.92 (d, J = 8.8 Hz, 2H),
3.82 (s, 3H), 3.10 (q, J = 8.8 Hz, 2H), 2.36 (s, 3H);ESIMS m/z341 ([M+H]+)。
7.60 - 7.50 (m, 4H), 7.47 (d, J = 8.0 Hz, 2H), 6.92 (d, J = 8.0 Hz, 2H), 3.82 (s, 3H), 3.20 (s, 2H);ESIMS m/z411 ([M+H]+)。
7.27 (d, J = 8.0 Hz, 4H), 6.90 (d, J = 8.0 Hz, 4H), 4.04 (q, J = 6.8 Hz, 4H), 3.09 (s, 2H), 1.42 (t, J = 6.8 Hz, 6H);ESIMS m/z 351 ([M+H]+)。
(E)-1,2,3-トリクロロ-5-(4-メトキシスチリル)ベンゼン(C44)
7.49 - 7.46 (m, 2H), 7.47 - 7.39 (m, 2H), 7.04 (d, J = 16.3 Hz, 1H), 6.93 - 6.89 (m, 2H), 6.78 (d, J= 16.3 Hz, 1H), 3.84 (s, 3H);13C NMR (101 MHz, CDCl3) δ 159.46, 135.08, 134.23, 130.91, 129.85, 129.16, 125.42, 114.02, 64.67, 55.32, 39.62, 38.48;EIMS m/z 313 ([M]+)。
(d, J = 16.5 Hz, 1H), 6.97 (d, J = 16.5 Hz, 1H), 6.91 (d, J = 9.0 Hz, 2H), 3.84
(s, 3H);ESIMS m/z 279 ([M+H]+)。
(E)-1-(4-メトキシスチリル)-3-(トリフルオロメチル)ベンゼン(C47)
7.72 (s, 1H), 7.64 (d, J = 6.8 Hz, 1H), 7.50 - 7.44 (m, 4H), 7.12 (d, J = 16.0 Hz, 1H), 6.98 (d, J = 16.0 Hz, 1H), 6.91 (d, J = 8.8 Hz, 2H), 3.84 (s, 3H);ESIMS m/z 279 ([M+H]+)。
7.88 (s, 2H), 7.70 (s, 1H), 7.49 (d, J = 8.4 Hz, 2H), 7.19 (d, J = 16.5 Hz, 1H), 6.99 (d, J = 16.5 Hz, 1H), 6.92 (d, J = 8.4 Hz, 2H), 3.84 (m, 3H);ESIMS m/z 347 ([M+H]+)。
7.53 (s, 1H), 7.50 (s, 2H), 7.43 (d, J = 9.0 Hz, 2H), 7.05 (d, J = 16.2 Hz, 1H), 6.90 (d, J = 9.0 Hz, 2H), 6.79 (d, J = 16.2 Hz, 1H), 3.80 (s, 3H); ESIMS m/z 367 ([M+H]+)。
- 6.85(m, 3H), 3.84 (s, 3H);ESIMS m/z 313 ([M+H]+)。
7.46 (s, 2H), 7.43 (d, J = 9.0 Hz, 2H), 7.07 (d, J = 13.5 Hz, 1H), 6.90 (d, J =
9.0 Hz, 1H), 6.73 (d, J = 13.5 Hz, 1H), 3.84 (s, 3H);ESIMS m/z 358 ([M+H]+)。
7.49 (s, 1H), 7.43 (d, J = 8.4 Hz, 2H), 7.38 (s, 1H), 7.35 (s, 1H), 7.05 (d, J = 16.5 Hz, 1H), 6.91 (d, J = 8.4 Hz, 2H), 6.80 (d, J = 16.5 Hz, 1H), 3.82 (s, 3H);ESIMS m/z 323 ([M+H]+)。
7.45 (d, J = 8.4 Hz, 2H), 7.10 - 7.0 (m, 3H), 6.96 - 6.80 (m, 4H), 3.80 (s, 3H);ESIMS m/z263 ([M+H]+)。
7.44 (d, J = 8.0 Hz, 2H), 7.35 - 7.31 (m, 1H), 7.28 - 7.24 (m, 1H), 7.17 (dd, J
= 1.6, 8.0 Hz, 1H), 7.03 (d, J = 16.0 Hz, 1H), 6.90 (d, J = 8.0 Hz, 1H), 7.49 (d, J = 8.0 Hz, 1H), 6.86 (d, J = 16.0 Hz, 1H), 3.82 (s, 3H);ESIMS m/z 263 ([M+H]+)。
7.44 (d, J = 8.4 Hz, 2H), 7.28 (s, 1H), 7.15 (s, 1H), 7.05 - 7.00 (m, 2H), 6.91
- 6.83 (m, 3H), 3.83 (s, 3H), 2.24 (s, 3H);ESIMS m/z 259 ([M+H]+)。
7.60 - 7.50 (m, 4H), 7.47 (d, J = 8.8 Hz, 2H),7.15 (d, J = 16.8 Hz, 1H), 6.98 (d, J = 16.8 Hz, 1H), 6.92 (d, J = 8.8 Hz, 2H), 3.82 (s, 3H);ESIMS m/z 329 ([M+H]+)。
7.40 (d, J = 9.0 Hz, 4H), 6.91 (s, 2H), 6.87 (d, J = 9.0 Hz, 4H), 4.05 (q, J = 6.9 Hz, 4H), 1.42 (t, J = 6.9 Hz, 6H);ESIMS m/z 269 ([M+H]+)。
ビニルベンゼン(1.32 g、9.80 mmol)と、トリエチルアミン(20 mL)との攪拌混合物を、アルゴン下で5分間脱気した。酢酸パラジウム(II)(0.0368 g、0.164 mmol)と1,1′-ビス(ジフェニルホスフィノ)フェロセン(0.181 g、0.328 mmol)とを加え、反応を90℃に16時間加熱した。反応混合物を水に注ぎ込み、酢酸エチルで抽出した。混合有機層を硫酸ナトリウムで乾燥し、濾過及び濃縮した。フラッシュカラムクロマトグラフィで精製することにより、表題化合物をオフホワイト色の固形物(1.60 g、67%)として得た:1H NMR (300 MHz, CDCl3) δ 7.41 (d, J = 8.8 Hz, 2H), 7.31 (s, 1H), 7.37 (s, 1H), 6.96
(d, J = 16.0 Hz, 1H), 6.89 (d, J = 8.8 Hz, 2H), 6.76 (d, J = 16.0 Hz, 1H), 3.84
(s, 3H);ESIMS m/z 297 ([M+H]+)。
(E)-1,3-ジクロロ-5-(4-メトキシスチリル)-2-メチルベンゼン(C61)
7.43 (d, J = 8.7 Hz, 2H), 7.38 (s, 2H), 7.02 (d, J = 16.5 Hz, 1H), 6.90 (d, J =
8.7 Hz, 2H), 6.79 (d, J = 16.5 Hz, 1H), 3.82 (s, 3H), 2.42 (s, 3H);ESIMS m/z 293 ([M+H]+)。
7.50 - 7.40 (m, 3H), 7.24 (s, 1H), 7.02 (d, J = 15.9 Hz, 1H), 6.90 (d, J = 9.0 Hz, 2H), 6.81 (d, J = 15.9 Hz, 1H), 3.83 (s, 3H), 2.42 (s, 3H);ESIMS m/z 293 ([M+H]+)。
mmol)を、暗色の溶液に攪拌しながら加えた。さらに0.5時間後、塩酸(1 N、100 mL)を攪拌しながら加えた。層を分離し、有機層をブラインで洗浄した。混合水層をエーテルで抽出し、混合有機層を硫酸ナトリウムで乾燥し、濾過及び濃縮して、表題化合物を白色の固形物(表題化合物:1,2,3-トリクロロベンゼンが10:1混合物、7.96 g、99%)として得た。1H NMR (CDCl3) δ 9.91 (s, 1H), 7.88 (s, 2H); EIMS m/z 209 ([M]+)。
(d, J = 9.0 Hz, 2H); EIMS m/z 274 ([M]+)。
ベンズアミド(F1)の調製
mmol)と1-エチル-3-(3-ジメチルアミノプロピル)カルボジイミド(0.127 g、0.660 mmol)との1,2-ジクロロエタン(4.40 mL)攪拌混合液に室温で順次加えた。反応を室温で20時間攪拌した。ジクロロメタンを加え、混合物を飽和炭酸水素ナトリウム水溶液と塩酸(1 N)とで洗浄した。有機相を硫酸マグネシウムで乾燥し、濾過及び濃縮して、表題化合物を黄色の固形物(0.0870 g、36%)として得た。
トランス-N-シクロプロピル-5-(2,2-ジクロロ-3-(3,5-ジクロロフェニル)シクロプロパンカルボキサミド)-2-(トリフルオロメチル)ベンズアミド(F2)
トランス-2-クロロ-5-(2,2-ジクロロ-3-(3,5-ジクロロ-4-フルオロフェニル)シクロプロパンカルボキサミド)-N-(3,3-ジフルオロシクロブチル)ベンズアミド(F30)
-フルオロフェニル)シクロプロパンカルボキサミド)ベンズアミド(F31)
ロフェニル)シクロプロパンカルボキサミド)ベンズアミド(F39)
トランス-2-クロロ-5-(2,2-ジクロロ-3-(3,5-ジクロロフェニル)シクロプロパンカルボキサミド)-N-(オキセタン-3-イル)ベンズアミド(F53)
ロロフェニル)シクロプロパンカルボキサミド)
ベンズアミド(F59)の調製
8.6, 2.9 Hz, 1H), 6.44 (s, 1H), 3.78 (s, 2H), 2.95 - 2.82 (m, 1H), 0.89 - 0.82 (m, 2H), 0.66 - 0.60 (m, 2H);EIMS m/z 211 ([M]+)。
5-アミノ-2-クロロ-N-(1-シアノシクロプロピル)ベンズアミド(C70)
, 1655 cm-1;EIMS m/z 236 ([M]+)。
DMSO-d6) δ 8.77 (d, J = 7 Hz, 1H), 7.06 (m, 1H), 6.56-6.61 (m, 2H), 5.41 (br s, 2H), 4.17 (m, 1H), 2.89-3.01 (m, 2H), 2.56-2.70 (m, 2H);IR (薄膜) 3482 (w), 3372 (w), 3251 (w), 2917 (m), 2850 (m), 1697 (w), 1631 (s), 1599 (s), 1577 (m), 1540 (s), 1478 (s) cm-1;ESIMS m/z 261 ([M+H]+)。
(s), 1599 (s), 1575 (m), 1520 (s), 1474 (s), 1432 (m) cm-1;ESIMS m/z 257 ([M+H]+)。
5-アミノ-2-クロロ-N-(1-シアノシクロブチル)ベンズアミド(C73)
5-アミノ-2-クロロ-N-(4,4-ジフルオロシクロヘキシル)ベンズアミド(C78)
N-シクロプロピル-5-ニトロ-2-(トリフルオロメチル)ベンズアミド(C80)
mmol)と、ジエチルイソプロピルエチルアミン(0.520 mL、2.98 mmol)と、1-エチル-3-(3-ジメチルアミノプロピル)-カルボジイミド(0.713 g、3.72 mmol)との1,2-ジクロロエタン(9.92 mL)溶液に室温で加えた。反応を室温で一晩攪拌した。反応混合物を酢酸エチルで希釈し、飽和炭酸水素ナトリウム水溶液で洗浄し、続いて塩酸(1 N)で洗浄した。有機相を硫酸マグネシウムで乾燥し、濾過及び濃縮して、表題化合物を白色の固形物(0.444 g、64%)として得た:1H NMR (400 MHz, DMSO-d6) δ 9.62 (s, 1H), 8.37 (d, J = 2.7 Hz, 1H), 8.31 (dd, J = 8.8, 2.8 Hz, 1H), 7.85 (d, J = 8.8 Hz, 1H), 1.59 (dd, J = 8.3, 5.4 Hz, 2H), 1.34 (dd, J = 8.4, 5.5 Hz, 2H);IR (薄膜) 3271, 3103,
2247, 1664 cm-1;ESIMS m/z 266 ([M+H]+)。
2-クロロ-N-(3,3-ジフルオロシクロブチル)-5-ニトロベンズアミド(C82)
(m, 2H);ESIMS m/z 291 ([M+H]+)。
に相分離器に注ぎ込み、濃縮して表題化合物を淡黄色の固形物(0.513 g、quant)として得た:1H NMR (400 MHz, CDCl3) δ 回転異性体 8.29 - 8.13 (m, 2H), 7.66 - 7.58 (m,
1H), 5.00 - 4.85 (m, 0.5 H), 4.05 - 3.92 (m, 0.5 H), 3.16 (s, 1.5 H), 3.10 - 2.95 (m, 1H), 2.87 (s, 1.5 H) 2.95 - 2.66 (m, 2H);19F NMR (376 MHz, CDCl3) δ 回転異性体-84.01 (d, J = 199.7 Hz), -84.85 (d, J = 202.6 Hz), -99.36 (d, J = 202.5
Hz), -99.67 (d, J = 199.7 Hz);ESIMS m/z 305 ([M+H]+)。
表P1:想定される分子の構造及び調製方法
トランス-3-(4-ブロモ-3-クロロフェニル)-2,2-ジクロロシクロプロパン-1-カルボン酸
(C84)
m/z 342.8
([M-H]-)。
.2 Hz, 1H);19F NMR (376 MHz, CDCl3) δ -103.87;ESIMS m/z 344.7 ([M-H]-)。
J = 7.9 Hz, 1H), 6.87 (d, J = 11.3 Hz, 1H), 3.91 (d, J = 3.8 Hz, 3H), 3.44 (d, J = 8.3 Hz, 1H), 2.80 (d, J = 8.3 Hz, 1H);19F NMR (376 MHz, CDCl3) δ -135.11;ESIMS m/z 356.7 ([M-H]-)。
10.5 (br s, 1H), 7.55 (s, 1H), 7.46 (d, J = 8.0 Hz, 1H), 7.34 (d, J = 8.4 Hz, 1H), 6.95 (t, J = 54.8 Hz, 1H), 3.50 (d, J = 8.4 Hz, 1H), 2.91 (d, J = 8.4 Hz, 1H);19F NMR (376 MHz, CDCl3) δ 115.52;ESIMS m/z 313 ([M-H]-)。
7.62 (t, J = 7.6 Hz, 1H), 7.18 (d, J= 7.6 Hz, 1H), 7.06 (d, J = 10.0 Hz, 1H), 6.89 (t, J = 54.8 Hz, 1H), 3.50 (d, J = 8.4 Hz, 1H), 2.90 (d, J = 8.4 Hz, 1H);19F NMR (376 MHz, CDCl3) δ 114.42, 118.63;ESIMS m/z 297.15 ([M-H]-)。
7.49 (br s, 2H), 7.41 (br s, 2H), 6.66 (t, J = 56.0 Hz, 1H), 3.53 (d,J = 8.4 Hz, 1H), 2.92 (d, J= 8.0 Hz, 1H);19F NMR (282 MHz, CDCl3) δ 111.20;ESIMS m/z 279.20 ([M-H]-)。
112.20;ESIMS m/z 279.30 ([M-H]-)。
トランス-1-クロロ-3-(2,2-ジクロロ-3-(4-メトキシフェニル)シクロプロピル)-5-(ジフルオロメチル)ベンゼン(C96)
56.1 Hz, 1H), 3.83 (s, 3H), 3.16 (q, J = 8.7 Hz, 2H)。
1H), 7.46 - 7.41 (m, 2H), 7.28 (d, J = 8.4 Hz, 2H), 7.10 - 6.83 (m, 3H), 3.83 (s, 3H), 3.18 - 3.13 (m, 2H)。
6.65 (t,J = 56.0 Hz, 2H), 3.83 (s, 3H), 3.16 (s, 2H)。
(m, 2H), 7.09 - 6.92 (m, 3H), 3.83 (s, 3H), 3.15 (q, J = 12.0 Hz, 2H);ESIMS m/z 376 ([M+H]+)。
(m, 4H), 3.83 (s, 3H), 3.16 (t, J = 8.8 Hz, 2H);19F NMR (376 MHz, CDCl3) δ -114.14,
-114.32, -119.30。
(s, 3H), 3.19 (s, 2H); 19F NMR (376 MHz, CDCl3) δ -110.87, -111.02。
8.0 Hz, 2H), 7.46 (d, J = 8.0 Hz, 2H), 7.28 (t, J = 8.4 Hz, 2H), 6.93 (d, J = 8.0 Hz, 2H), 6.67 (t, J = 56.8 Hz, 1H), 3.83 (s, 3H), 3.18 (s, 2H)。
トランス-5-(3-(4-ブロモ-3-クロロフェニル)-2,2-ジクロロシクロプロパン-1-カルボキサミド)-2-クロロ-N-(1-シアノシクロプロピル)ベンズアミド(F66)
トランス-2-クロロ-5-(2,2-ジクロロ-3-(3,5-ジクロロフェニル)シクロプロパン-1-カルボキサミド)-N-(4-オキソシクロヘキシル)ベンズアミド(F65)
2-クロロ-5-((1R,3R)-2,2-ジクロロ-3-(3,5-ジクロロフェニル)シクロプロパンカルボキサミド)-N-(3,3-ジフルオロシクロブチル)ベンズアミド(F73)
5-アミノ-2-クロロ-N-(1-シアノシクロプロピル)-N-メチルベンズアミド(C104)
(s, 2H);IR (薄膜) 3360, 2236, 1654, 1477, 1374 cm-1;ESIMS m/z 250 ([M+H]+)。
(R)-5-アミノ-2-クロロ-N-(3-オキソ-2-(2,2,2-トリフルオロエチル)イソオキサゾリジン-4-イル)ベンズアミド(C106)
5-アミノ-2-クロロ-N-(1,1-ジオキシドテトラヒドロチオフェン-3-イル)ベンズアミド(C107)
DMSO-d6) δ 8.76 (d, J= 7 Hz, 1H), 7.07 (d, J = 8 Hz, 1H), 6.63 - 6.55 (m, 2H),
5.42 (br s, 2H), 4.60 (m, 1H), 3.49 (dd, J = 13.5, 7.8 Hz, 1H), 3.31 (m, 1H), 3.18 (m, 1H), 2.97 (dd, J= 13, 7.2 Hz, 1H), 2.41 (m, 1H), 2.12 (m, 1H);IR (薄膜)
3458 (w), 3370 (w), 3257 (w), 1646 (m), 1535 (m), 1479 (w) cm-1;ESIMS m/z 289 ([M+H]+)。
(R)-2-クロロ-5-ニトロ-N-(3-オキソ-2-(2,2,2-トリフルオロエチル)イソオキサゾリジン-4-イル)ベンズアミド(C108)
NMR (376 MHz, DMSO-d6) δ -69.11;ESIMS m/z 368 ([M+H]+)。
2-クロロ-N-(1-シアノシクロプロピル)-N-メチル-5-ニトロベンズアミド(C109)
mg、0.478 mmol)を加えて、得られた黄白色の溶液を室温で約14時間攪拌した。溶液を窒素流下で濃縮し、ヘキサン類/酢酸エチルの移動相を用いたシリカゲルフラッシュカラムクロマトグラフィで精製した。純粋な画分を混合し、ロータリーエバポレータによる減圧下で濃縮して、表題化合物を白色の泡状物(0.080 g、59%)として得た。
シス-2-クロロ-5-(2,2-ジクロロ-3-(3,5-ジクロロフェニル)-3-メチルシクロプロパン-1-カルボキサミド)-N-(3,3-ジフルオロシクロブチル)ベンズアミド(F62)
メチル)-4-フルオロフェニル)シクロプロパン-1-カルボキサミド)ベンズアミド(F88)
メチル)フェニル)シクロプロパン-1-カルボキサミド)ベンズアミド(F92)
mL、0.99 mmol)を加え、次いで50%の2,4,6-トリプロピル-1,3,5,2,4,6-トリオキサトリホスフィナン2,4,6-トリオキシド(T3P(登録商標))酢酸エチル溶液(300 μL、0.50 mmol)を加えた。反応混合物を50℃に加熱し、18時間攪拌した。反応混合物を濃縮し、残渣を5%〜100%のアセトニトリル/水を溶離液として用いる逆相フラッシュカラムクロマトグラフィで精製して、表題生成物を白色の粉末(0.031 g、18%)として得た。
トランス-2-クロロ-5-(2,2-ジクロロ-3-(3-クロロ-4-フルオロフェニル)シクロプロパン-1-カルボキサミド)-N-(4-オキソシクロヘキシル)ベンズアミド(F81)
トランス-2-クロロ-5-(2,2-ジクロロ-3-(3,5-ジクロロフェニル)シクロプロパン-1-カルボキサミド)-N-(1-(3,3,3-トリフルオロプロパノイル)アゼチジン-3-イル)ベンズアミド(PF12)
パンカルボキサミド)-N-(1-メチルシクロプロピル)ベンズアミド(PF32)の調製
トランス-メチル 1-(2-クロロ-5-(2,2-ジクロロ-3-(3,5-ジクロロフェニル)シクロプロパンカルボキサミド)ベンズアミド)シクロペンタンカルボキシレート(PF33)
以下の化合物を、実施例36に概説した手順と同様の方法で調製した:
トランス-2,2-ジクロロ-3-(3,4,5-トリクロロフェニル)シクロプロパン-1-カルボン酸(C2)
(dd, J = 8.4, 2.1 Hz, 1H), 3.49 (s, 2H)。13C NMR (126 MHz, DMSO-d6) δ 166.34 ,
133.35 , 130.47 , 130.33 , 130.09 , 129.77 , 128.81 , 61.43 , 37.00 , 36.06。
([M-H]-)。
実施例37:トランス-2,2-ジブロモ-3-(3,5-ジクロロフェニル)シクロプロパン-1-カルボン酸(C111)の調製
1.9 Hz, 1H), 7.17 (dd, J = 1.9, 0.8 Hz, 2H), 3.39 (d, J = 8.2 Hz, 1H), 2.91 (d,
J = 8.2 Hz, 1H);13C NMR (101 MHz, CDCl3) δ 172.15, 136.91, 135.25, 128.64, 127.29, 40.29, 37.32, 26.57;ESIMS m/z 386 ([M-H]-)。
mL)攪拌溶液に5℃で加えた。混合液を0℃〜5℃で2時間攪拌し、続いて室温で12時間攪
拌した。得られた褐色の懸濁液を5℃に冷却し、イソプロピルアルコール(20 mL)、次いで水(100 mL)でクエンチした。混合物を酢酸エチル(3×50 mL)で抽出した。混合有機抽出物を水とブラインとで洗浄し、無水硫酸マグネシウムで乾燥し、濾過し、またロータリーエバポレータによる減圧下で濃縮した。粗生成物を、アセトニトリル/水を溶離液として用いるC-18フラッシュクロマトグラフィで精製し、トランス-2,2-ジクロロ-3-(3,5-ジクロロフェニル)-3-メチルシクロプロパンカルボン酸(0.727 g 59%)を白色の固形物として得た:1H NMR (400 MHz, アセトン-d6) δ 7.49 (dd, J = 18.6, 1.9 Hz, 3H), 3.11 (s, 1H), 1.78 (s, 3H);13C NMR (101 MHz, アセトン-d6) δ 166.55, 146.09, 135.70, 129.69, 128.49, 128.26, 66.75, 41.87, 39.59, 30.41, 30.21, 30.02, 29.83, 29.64, 29.55, 29.45, 29.25, 20.18;ESIMS m/z313 ([M-H]-)。
シス-2,2-ジクロロ-3-(3,5-ジクロロフェニル)-3-メチルシクロプロパン-1-カルボン酸(C113)
20.20;ESIMS m/z 313 ([M-H]-)。
mL)攪拌溶液に加えた。混合物を20℃で16時間攪拌した。得られた混合物を水(200 mL)で希釈し、濃縮してアセトニトリルを除去した。得られた水溶性混合物をヘキサン類(600 mL)で抽出した。有機層を水(300 mL)で洗浄し、無水硫酸ナトリウムで乾燥し、濾過及び濃縮した。粗生成物を0%〜20%の酢酸エチル/ヘキサン類を溶離液として用いるフラッシュカラムクロマトグラフィで精製して、表題生成物を黄色の油状物(58.7 g、86%、純度95%)として得た:1H NMR (400 MHz, CDCl3) δ 9.54 (d, J = 4.0 Hz, 1H), 7.46
- 7.09 (m, 3H), 3.51 (d, J = 8.0 Hz, 1H), 2.92 (dd, J = 8.0, 4.0 Hz, 1H);13C NMR (126 MHz, CDCl3) δ 193.41, 135.33, 135.09, 128.78, 127.34, 42.89, 39.31;IR (薄膜) 3078, 2847, 1714, 1590, 1566, 1417, 1387。
トランス-2,2-ジクロロ-3-(3,4-ジクロロフェニル)シクロプロパン-1-カルボアルデヒド(C116)
= 8.0, 3.7 Hz, 1H)。
することにより溶出液を得、次いで、得られた溶出液をアセトン(4 mL)と塩酸水溶液(2 N、1 mL、2 mmol)とに溶解した。混合物を一晩攪拌した。混合物を、その溶液のpHが7より大きくなるまで、飽和炭酸水素ナトリウム溶液で希釈した。次いで、混合物をジエチルエーテルと酢酸エチルとで抽出し、混合有機層を硫酸ナトリウムで乾燥し、濃縮して、濃褐色の生成物(0.03 g、4%)を得た:1H NMR (400 MHz, CDCl3) δ 9.48 (d, J = 4.0 Hz, 1H), 7.37 (t, J = 1.9 Hz, 1H), 7.17 (dd, J = 1.9, 0.7 Hz, 2H), 3.60 - 3.36 (m, 1H), 2.90 (dd, J = 7.9, 4.0 Hz, 1H);13C NMR (101 MHz, CDCl3) δ 194.74, 136.55, 135.31, 128.76, 127.34, 42.34, 39.84, 26.05;ESIMS m/z 343 ([M-CHO]-)。
4H), 2.77 (d, J = 8.5 Hz, 1H), 2.25 (dd, J = 8.5, 6.2 Hz, 1H), 1.30 (t, J = 7.0
Hz, 3H), 1.20 (t, J = 7.1 Hz, 3H)。
1,2-ジクロロ-4-(トランス-2,2-ジクロロ-3-(ジエトキシメチル)シクロプロピル)ベンゼン(C122)
16.1, 1.2 Hz, 1H), 6.14 (dd, J = 16.1, 5.0 Hz, 1H), 5.05 (dd, J = 4.9, 1.2 Hz, 1H), 3.70 (dq, J = 9.3, 7.0 Hz, 2H), 3.56 (dq, J = 9.4, 7.1 Hz, 2H), 1.25 (t, J = 7.1 Hz, 6H);13C NMR (101 MHz, CDCl3) δ 158.91, 156.42, 133.65, 133.62, 130.47, 128.65, 128.07, 128.05, 126.39, 126.32, 121.26, 121.08, 116.72, 116.51, 100.93, 61.17, 15.24;19F NMR (376 MHz, CDCl3) δ -116.36。
Hz, 3H)。
Hz, 1H), 1.31 (t, J = 7.1 Hz, 3H), 1.21 (t, J = 7.0 Hz, 3H)。
(E)-1,2-ジクロロ-4-(3,3-ジエトキシプロプ-1-エン-1-イル)ベンゼン(C127)
4H), 1.25 (td, J= 7.1, 0.8 Hz, 6H)。
= 7.0, 2.2 Hz, 1H), 7.29 - 7.22 (m, 1H), 7.09 (t, J= 8.7 Hz, 1H), 6.62 (dd, J =
16.1, 1.2 Hz, 1H), 6.14 (dd, J= 16.1, 5.0 Hz, 1H), 5.05 (dd, J= 4.9, 1.2 Hz, 1H), 3.70 (dq, J= 9.3, 7.0 Hz, 2H), 3.56 (dq, J= 9.4, 7.1 Hz, 2H), 1.25 (t, J= 7.1
Hz, 6H);13C NMR (101 MHz, CDCl3) δ 158.91, 156.42, 133.65, 133.62, 130.47, 128.65, 128.07, 128.05, 126.39, 126.32, 121.26, 121.08, 116.72, 116.51, 100.93, 61.17, 15.24;19F NMR (376 MHz, CDCl3) δ -116.36。
6.58 (dd, J = 16.1, 1.2 Hz, 1H), 6.21 (dd, J= 16.1, 4.6 Hz, 1H), 5.06 (dd, J= 4.7, 1.2 Hz, 1H), 3.69 (dq, J= 9.3, 7.1 Hz, 2H), 3.55 (dq, J= 9.5, 7.0 Hz, 2H), 1.25 (t, J= 7.1 Hz, 6H)。
= 1.8 Hz, 1H), 7.58 - 7.53 (m, 1H), 7.51 (t, J = 1.7 Hz, 1H), 6.72 - 6.61 (m, 1H), 6.28 (dd, J= 16.1, 4.5 Hz, 1H), 5.09 (dd, J= 4.5, 1.3 Hz, 1H), 3.70 (dq, J= 9.4, 7.1 Hz, 2H), 3.56 (dq, J= 9.4, 7.0 Hz, 2H), 1.26 (t, J= 7.0 Hz, 6H)。
mmol)を加えた。得られた黄白色の油懸濁液を室温で12時間攪拌した。反応を飽和塩化アンモニウム水溶液(100 mL)でクエンチした。混合水溶液をエチルエーテル(3×50 mL)で抽出した。混合有機抽出物を水とブラインとで洗浄し、無水硫酸マグネシウムで乾燥し、濾過し、またロータリーエバポレータによる減圧下で濃縮した。粗生成物をシリカゲルフラッシュクロマトグラフィ(ヘキサン類/酢酸エチル移動相)で精製して、エチル-3-(3,5-ジクロロフェニル)ブタ-2-エノアート(5.69 g、79%)をE-(85%)異性体及びZ-(15%)異性体の混合物として得た。
(E)-2-((3-(4-ニトロフェニル)アリル)オキシ)テトラヒドロ-2H-ピラン(C134)
3.65 - 3.47 (m, 1H), 1.96 - 1.36 (m, 6H);13C NMR (101 MHz, CDCl3) δ 146.95, 143.36, 131.36, 129.36, 126.93, 123.98, 98.33, 67.10, 62.34, 30.58, 25.41, 19.44;IR (薄膜) 2939, 2849, 1595, 1513, 1339 cm-1。
ロホルム(20 mL)攪拌溶液に少量ずつ加えた。得られた黄色の固体懸濁液を、55℃に合計7時間加熱し、室温でさらに12時間攪拌した。反応混合物を水(100 mL)でクエンチし、エーテル(3×50 mL)で抽出した。混合有機抽出物を水とブラインとで洗浄し、無水硫酸マグネシウムで乾燥し、濾過し、またロータリーエバポレータによる減圧下で濃縮した。粗生成物をシリカゲルフラッシュクロマトグラフィ(ヘキサン類/酢酸エチル移動相)で精製して、トランス-2-((2,2-ジクロロ-3-(3,5-ジクロロフェニル)-3-メチルシクロプロピル)メトキシ)テトラヒドロ-2H-ピラン(2.03 g、69%)を透明な無色の油状物として得た。
わたり53%)として得た:1H NMR (400 MHz, CDCl3) δ 8.22 (d, J = 8.7 Hz, 2H), 7.52
- 7.34 (m, 2H), 4.10 (ddd, J= 12.4, 7.2, 5.3 Hz, 1H), 3.95 (ddd, J= 12.0, 8.0, 5.0 Hz, 1H), 2.78 (d, J= 8.3 Hz, 1H), 2.37 (td, J = 8.2, 5.4 Hz, 1H);13C NMR (101 MHz, CDCl3) δ 147.43, 141.42, 129.77, 123.59, 63.74, 62.25, 38.50, 37.04;IR
(薄膜) 1598, 1514, 1345, 1046 cm-1;HRMS-ESI (m/z) [M+Na]+ C10H9Cl2NO3Naの計算値, 283.9852; 実測値, 283.9844。
2-ブロモ-5-(トランス-2,2-ジクロロ-3-(4-メトキシフェニル)シクロプロピル)-1,3-ジフルオロベンゼン(C139)
CDCl3) δ 161.10, 159.49, 129.86, 125.47, 114.04, 112.79, 112.56, 112.53, 64.66, 55.33, 39.77, 39.01;19F NMR (376 MHz, CDCl3) δ -104.75。
オロ-3-メトキシベンゼン(C140)
3.96 (s, 3H), 3.83 (s, 3H), 3.15 - 3.07 (m, 2H);13C NMR (101 MHz, CDCl3) δ 161.20, 159.43, 136.09, 135.99, 129.91, 125.85, 114.01, 109.29, 109.05, 108.20, 64.91, 56.79, 55.33, 39.59, 39.49;19F NMR (376 MHz, CDCl3) δ -104.96。
7.58 - 7.53 (m, 2H), 7.47 - 7.39 (m, 2H), 7.22 (dd, J= 8.4, 2.1 Hz, 1H), 7.06 (d, J= 16.2 Hz, 1H), 6.95 - 6.87 (m, 2H), 6.84 (d, J = 16.3 Hz, 1H), 3.84 (s, 3H);EIMS m/z 324。
(d, J = 8.6 Hz, 2H), 7.06 (d, J = 16.2 Hz, 1H), 6.91 (dd, J = 9.1, 2.2 Hz, 3H),
6.86 (d, J = 16.2 Hz, 1H), 6.78 (t, J = 1.5 Hz, 1H), 3.96 (s, 3H), 3.84 (s, 3H);19F NMR (376 MHz, CDCl3) δ -106.15;EIMS m/z 336.0。
シウムで乾燥し、濾過及び濃縮した。0%〜10%の酢酸エチルを溶離液として用いるフラッシュカラムクロマトグラフィで精製することにより、(E)-1-ブロモ-3-フルオロ-2-メトキシ-5-(4-メトキシスチリル)ベンゼンを白色の固形物(0.48 g、20%)として得た:融点78.0℃〜84.8℃;1H NMR (400 MHz, CDCl3) δ 7.47 (d, J = 8.7 Hz, 2H), 7.39 (d, J = 12.5 Hz, 1H), 7.19 (dd, J = 16.1, 1.7 Hz, 1H), 7.14 (d, J = 8.1 Hz, 1H), 6.94 - 6.89 (m, 2H), 6.86 (d, J = 16.2 Hz, 1H), 3.90 (s, 3H), 3.84 (s, 3H);19F NMR (376 MHz, CDCl3) δ -135.86;EIMS m/z 336.0。
mmol)とを加え、得られた反応混合物を100℃に16時間加熱した。反応混合物を水に注ぎ込み、酢酸エチルで抽出した。混合有機層を硫酸ナトリウムで乾燥し、減圧下で濃縮した。得られた粗物質を石油エーテル中の5〜10%酢酸エチルを溶離液として用いるフラッシュカラムクロマトグラフィで精製して、表題化合物を黄色の固形物(13.5 g、54%)として得た:1H NMR (300 MHz, CDCl3) δ 9.99 (s, 1H), 7.85 (s, 1H), 7.69 (s, 2H), 7.47 (d, J = 8.4 Hz, 2H), 7.16 (d,J = 16.2 Hz, 1H), 6.94 (t, J = 8.4 Hz, 3H), 3.84 (s, 3H); ESIMS m/z 273 ([M+H]+)。
(E)-2-クロロ-5-(4-メトキシスチリル)ベンズアルデヒド(C147)
= 16.4 Hz, 1H), 6.95 - 6.90 (m, 3H), 3.95 (s, 3H);ESIMS m/z 273 ([M+H]+)。
10.41 (s, 1H), 7.97 (dd, J = 2.4, 6.8 Hz, 1H), 7.71 - 7.67 (m, 1H), 7.44 (d, J = 8.0 Hz, 2H), 7.18 - 7.13 (m, 1H), 7.08 - 7.04 (m, 1H), 6.95 - 6.90 (m, 3H), 3.85 (s, 3H);ESIMS m/z257 ([M+H]+)。
7.23 (t,J = 7.6 Hz, 1H), 7.00 (d, J = 16.0 Hz, 1H), 6.92 (d, J = 8.8 Hz, 2H), 3.84 (s, 3H)。
8.8 Hz, 3H), 7.34 (s, 1H), 7.10 (d, J = 16 Hz, 1H), 6.90 (t, J = 8.4 Hz, 3H), 6.61 (t, J = 56.4 Hz, 1H), 3.80 (s, 3H); 19F NMR (376 MHz, CDCl3) δ -111.72。
(E)-1-クロロ-2-(ジフルオロメチル)-4-(4-メトキシスチリル)ベンゼン(C155)
7.46 (d, J = 8.0 Hz, 2H), 7.38 (s, 1H), 7.28 (s, 1H), 7.08 (t, J = 16.2 Hz, 2H), 6.92 (t, J = 15.6 Hz, 3H), 6.63 (t, J = 56.0 Hz, 1H), 3.84 (s, 3H);ESIMS m/z 279 ([M+H]+)。
- 7.06 (m, 2H), 7.00 - 6.89 (m, 4H), 3.85 (s, 3H);ESIMS m/z 279 ([M+H]+)。
56 (m, 2H), 7.48 - 7.34 (m, 4H), 7.11 (d, J = 16.5 Hz, 1H), 7.00 (s, 1H), 6.95- 6.89 (t, 2H), 6.66 (t, 1H), 3.95 (s, 3H);19F NMR (282 MHz, CDCl3) δ -110.84;ESIMS m/z 261 ([M+H]+)。
J = 57 Hz, 1H), 3.92 (s, 3H); ESIMS m/z 260.17 ([M+H]+)。
s, 3H), 3.92 (m, 1H), 3.44 - 3.34 (m, 2H), 3,32 - 3.22 (m, 2H)。
N)で洗浄し、続いて、飽和炭酸水素ナトリウム水溶液、次いでブラインで洗浄した。有機層を濃縮し、残渣を0%〜30%の酢酸エチル/ヘキサン類を用いるカラムクロマトグラフィで精製して、表題化合物を白色の固形物(0.058 g、21%)として得た:1H NMR (400 MHz, CDCl3) δ 8.57 (d, J = 2.7 Hz, 1H), 8.26 (dd, J = 8.8, 2.8 Hz, 1H), 7.63 (d, J = 8.8 Hz, 1H), 6.53 (s, 1H), 3.70 - 3.52 (m, 1H), 2.05 - 1.91 (m, 1H), 1.62 -
1.48 (m, 1H);IR (薄膜) 3268, 1661, 1538 cm-1;ESIMS m/z 277 ([M+H]+)。
g、97% ee、24.2%)として得た:比旋光度:+47.4(アセトニトリル溶液10 mg/mL、589 nm、25.2℃);1H NMR (300 MHz, CDCl3) δ 7.36 (t, J = 1.9 Hz, 1H), 7.17 (dd, J =
1.9, 0.7 Hz, 2H), 3.48 - 3.37 (m, 1H), 2.87 (d, J = 8.3 Hz, 1H);13C NMR (400 MHz, DMSO-d6) δ 166.28, 136.40, 133.39, 127.27, 127.04, 61.36, 37.10, 35.98;ESIMS m/z 298.9 ([M-H]-)。
以下の化合物を、実施例57に概説した手順と同様の方法で調製した:
(1R,3R)-2,2-ジクロロ-3-(3,4-ジクロロフェニル)シクロプロパン-1-カルボン酸(C165)
(1R,3R)-2,2-ジクロロ-3-(3-クロロ-4-フルオロフェニル)シクロプロパン-1-カルボン酸(C166)
(1R,3R)-2,2-ジクロロ-3-(3,4,5-トリクロロフェニル)シクロプロパン-1-カルボン酸(C167)
実施例58:(1S,3S)-2,2-ジクロロ-3-(3,5-ジクロロフェニル)-シクロプロパン-1-カルボン酸(C168)
eeは、以下のようにキラルHPLC法で測定した:カラム:CHIRALPAK@ ZWIX(+)、粒子サイズ3 μm、寸法3 mm×150 mmL、DAIC 511584;移動相:49%アセトニトリル/49%メタノール/水(50 mMギ酸及びジエチルアミンを添加);流速:0.5 mL/min;時間:9分;温度:25℃
以下の化合物を、実施例58に概説した手順と同様の方法で調製した:
(1S,3S)-2,2-ジクロロ-3-(3,4-ジクロロフェニル)シクロプロパン-1-カルボン酸(C169)
(1S,3S)-2,2-ジクロロ-3-(3-クロロ-4-フルオロフェニル)シクロプロパン-1-カルボン酸(C170)
(1S,3S)-2,2-ジクロロ-3-(3,4,5-トリクロロフェニル)シクロプロパン-1-カルボン酸(C171)
シロイチモジヨトウ(スポドプテラ・エクシグア(Spodoptera exigua))、イラクサキンウワバ(トリコプルシア・ニ(Trichoplusia ni))、モモアカアブラムシ(ミズス
・ペルシカエ(Myzus persicae))、及びネッタイシマカ(アエデス・アエジプチ(Aedes aegypti))に対する以下のバイオアッセイが、これらがもたらす被害に伴い、本明細書に含まれる。また、シロイチモジヨトウ及びイラクサキンウワバは、種々の咀嚼害虫に対する2つの良い指標種である。加えて、モモアカアブラムシは、種々の樹液を食する害虫に対する良い指標種である。ネッタイシマカと共にこれらの3つの指標種を用いた結果により、式1の分子が、節足動物門、軟体動物門、及び線形動物門の害虫を防除するのに広く有益であることが示される(Drewes et al.)。
シロイチモジヨトウは、作物の中でも、アルファルファ、アスパラガス、ビーツ、柑橘類、トウモロコシ、ワタ、タマネギ、エンドウ、コショウ、ジャガイモ、ダイズ、テンサイ、ヒマワリ、タバコ、及びトマトに対して、経済的懸念となる深刻な害虫である。東南アジア原産であるが、今ではアフリカ、オーストラリア、日本、北米、及び南ヨーロッパで発見される。幼虫は大群で餌を食し、壊滅的な作物の損失を引き起こす場合がある。いくつかの農薬に耐性があることが知られている。
BAWに関するバイオアッセイを128ウェルダイエットトレイアッセイを使用して実施した。1〜5匹の二齢BAW幼虫を、ダイエットトレイの各ウェル(3mL)内に置いたが、各ウェルは、50μg/cm2の試験分子(90:10のアセトン-水混合液50μLに溶解)を(8ウェルの各々に)加え、その後乾燥させた約1.5 mLの人工餌で予め満たしていた。トレイを透明な自己接着性カバーで覆い、ガス交換ができるように通気孔を開け、25℃、14:10の明−暗で5〜7日間保持した。死亡率を各ウェル中の幼虫に対して記録し、その後、8ウェル中の活性を平均化した。その結果を「表ABC:生物学的結果」と題する表に示す(表セクションを参照)。
CLに関するバイオアッセイを128ウェルダイエットトレイアッセイを使用して実施した。1〜5匹の二齢CL幼虫を、ダイエットトレイの各ウェル(3mL)内に置いたが、各ウェルは、50μg/cm2の試験分子(90:10のアセトン-水混合液50μLに溶解)を(8ウェルの各々
に)加え、その後乾燥させた1 mLの人工餌で予め満たしていた。トレイを透明な自己接着性カバーで覆い、ガス交換ができるように通気孔を開け、25℃、14:10の明−暗で5〜7日間保持した。死亡率を各ウェル中の幼虫に対して記録し、その後、8ウェル中の活性を平均化した。その結果を「表ABC:生物学的結果」と題する表に示す(表セクションを参照)。
GPAは、モモの木の最も影響のあるアブラムシ害虫であり、成長の低下、葉のしぼみ、及び種々の組織の死をもたらす。またGPAは、植物ウイルス、例えばジャガイモウイルスY及びジャガイモ葉巻病ウイルスをナス/ジャガイモ科ソラナセアエ(Solanaceae)のメンバへ輸送するための、ならびに種々のモザイクウイルスを他の多くの食用作物へ輸送するための媒介物として作用するので、有害である。GPAは、作物の中でも、ブロッコリ、ゴボウ、キャベツ、ニンジン、カリフラワ、ダイコン、ナス、インゲンマメ、レタス、マカダミア、パパイヤ、コショウ、サツマイモ、トマト、クレソン及びズッキーニなどの植物を攻撃する。GPAはカーネーション、キク、ハボタン(flowering white cabbage)、ポインセチア、及びバラなどの多くの観賞用作物も攻撃する。GPAは多くの農薬に対する耐性を発現している。現在、昆虫抵抗性の報告例のうち3番目に数が多いのが害虫である(Sparks et al.)。したがって、上述の要因により、この害虫を防除することが重要である。さらに、樹液を食する害虫として知られるこの害虫(GPA)を防除する分子は、植物からの樹液を食する他の害虫の防除に有益となる。
YFMは、日中ヒトを餌にすることを好み、ヒト居住地内またはその近くで発見されることが最も多い。YFMは数種の疾患を伝染させる媒介物である。それはデング熱及び黄熱病のウイルスを蔓延させ得る蚊である。黄熱病は、マラリアに次ぐ2番目に危険な蚊媒介性疾患である。黄熱病は急性ウイルス性出血性疾患であり、治療をしない場合には重度に冒された人の50%までもが黄熱病が原因で死亡するであろう。黄熱病は、毎年世界で推定20万の症例があり、3万人の死亡を引き起こしている。デング熱は厄介なウイルス性疾患で
あり、それがもたらし得る強い痛みのため、「骨折熱」または「心臓破りの熱(break-heart fever)」と呼ばれる場合がある。デング熱は、毎年約2万人の人々を死に至らしめている。したがって、上述の要因により、この害虫を防除することが重要である。さらに、吸血性害虫として知られるこの害虫(YFM)を防除する分子は、ヒト及び動物に疾苦を引き起こす他の害虫の防除に有益である。
式1の分子は、農学的に許容可能な酸付加塩にすることができる。非限定的な例として、アミン官能基は、塩酸、臭化水素酸、硫酸、リン酸、酢酸、安息香酸、クエン酸、マロン酸、サリチル酸、リンゴ酸、フマル酸、シュウ酸、コハク酸、酒石酸、乳酸、グルコン酸、アスコルビン酸、マレイン酸、アスパラギン酸、ベンゼンスルホン酸、メタンスルホン酸、エタンスルホン酸、ヒドロキシメタンスルホン酸、及びヒドロキシエタンスルホン酸と、塩を形成することができる。さらに、非限定的な例として、酸官能基は、アルカリ金属またはアルカリ土類金属由来の塩ならびにアンモニア及びアミン由来の塩を含む塩を形成することができる。好ましいカチオンの例として、ナトリウム、カリウム、及びマグネシウムが挙げられる。
本発明の別の実施形態では、式1の分子は1つ以上の活性成分と組み合わせて(例えば、組成混合で、または同時適用もしくは逐次適用で)使用され得る。
農薬は、その純粋な形態で適用に適していることがほとんどない。通例、農薬を所要濃度かつ適正な形態で使用して、適用、処理、輸送、貯蔵を容易にし、及び最大農薬作用をもたらすことができるように、他の物質を加えることが必要である。したがって、農薬は、例えば、ベイト剤、濃縮乳濁液、粉末、乳剤、燻蒸剤、ゲル剤、顆粒剤、マイクロカプセル化剤、種子処理剤、懸濁液濃縮物、サスポエマルジョン剤、錠剤、水溶性液体、水分散性顆粒剤またはドライフロワブル剤、水和剤、及び極小量溶液に配合される。
かく分散された有機溶媒不溶性農薬の懸濁液を含む。1つ以上の農薬が、有機溶媒に溶解されてもよい。有用な有機溶媒として、芳香族、特にキシレン及び石油留分、特に石油のうちの高沸点ナフタレン部分及びオレフィン部分(重質芳香族ナフサなど)が挙げられる。他の溶媒として、植物油、種油、ならびに植物油及び種油のエステル類が挙げられ得る。油分散液に適切な乳化剤は、従来の陰イオン性及び非イオン性界面活性剤から選択される。増粘剤またはゲル化剤が、液体のレオロジまたは流動特性を変えるために、ならびに分散した粒子または液滴の分離及び沈降を阻止するために、油分散液の製剤に添加される。
の活性成分が放出される速度を制御し、これが残留性能、作用速度、及び生成物の臭気に影響を及ぼす。マイクロカプセルは、懸濁液濃縮物または水分散性顆粒剤として製剤化される場合もある。
一般的に、式1で開示される分子を製剤で使用する場合、かかる製剤は他の成分も含有することができる。これらの成分として、限定されないが(これは非網羅的であり、及び非相互排他的なリストである)湿潤剤、展着剤、固着剤、浸透剤、緩衝剤、金属イオン封鎖剤、ドリフト低減剤、相溶化剤、消泡剤、洗浄剤、及び乳化剤が挙げられる。いくつかの成分を直下に記載する。
疎水性の主鎖が粒子表面上への多数の固着点を有するので、これら高分子量ポリマーは、極めて優れた長期安定性を懸濁液濃縮物に付与することができる。農薬製剤に使用される分散剤の例として、ナトリウムリグノスルホネート類、ナトリウムナフタレンスルホン酸ホルムアルデヒド縮合物、トリスチリルフェノールエトキシレートホスフェートエステル類、脂肪族アルコールエトキシレート類、アルキルエトキシレート類、EO-POブロックコポリマー、及びグラフトコポリマーがある。
濁液濃縮物における水溶性多糖類は、増粘ゲル化剤として長年の間使用されてきた。最も一般的に使用されている多糖類の種類は、種子及び海藻の天然抽出物であるか、またはセルロースの合成誘導体である。これらの種の物質の例として、限定されないが、グアーガム、ローカストビーンガム、カラギーナン、アルギン酸塩類、メチルセルロース、カルボキシメチルセルロースナトリウム(SCMC)、及びヒドロキシエチルセルロース(HEC)が挙げられる。他の種類の沈降防止剤は、加工デンプン類、ポリアクリレート類、ポリビニルアルコール及びポリエチレンオキシドをベースにする。別の優れた沈降防止剤はキサンタンガムである。
式1の分子は任意の領域に適用され得る。かかる分子を適用する特定の領域は、アルファルファ、アーモンド、リンゴ、オオムギ、マメ、カノーラ、トウモロコシ、ワタ、カリフラワ、花、飼葉種(ライグラス、スーダングラス、ヒロハノウシノケグサ、ナガハグサ、及びクローバー)、果実、レタス、カラスムギ、脂肪種子作物、オレンジ、ピーナッツ、セイヨウナシ、コショウ、ジャガイモ、イネ、ソルガム、ダイズ、イチゴ、サトウキビ、テンサイ、ヒマワリ、タバコ、トマト、コムギ(例えば、ハードレッドウィンター小麦、ソフトレッドウィンター小麦、ホワイトウィンター小麦、ハードレッドスプリング小麦、及びデュラムスプリング小麦)、ならびに他の有価作物が育てられているか、またはその種子が植えられる予定の領域を含む。
収穫時のより高い収率につながり得る。一般的に、種子10万個当たりかかる分子約1グラム〜約500グラムで優れた利点が得られることが予測され、種子10万個当たり約10グラム〜約100グラムの量で、より優れた利点が得られることが予測され、種子10万個当たり約25グラム〜約75グラムの量で、さらに優れた利点が得られることが予測される。
1D. 以下の式を有する分子
(A) R1は、H、F、Cl、Br、I、CN、NH2、NO2、(C1-C4)アルキル、(C3-C6)シクロアルキル、(C2-C4)アルケニル、(C3-C6)シクロアルケニル、(C2-C4)アルキニル、(C1-C4)アルコキシ、(C1-C4)ハロアルキル、(C3-C6)ハロシクロアルキル、(C2-C4)ハロアルケニル、(C3-C6)ハロシクロアルケニル、(C1-C4)ハロアルコキシ、S(C1-C4)アルキル、S(O)(C1-C4)アルキル、S(O)2(C1-C4)アルキル、S(C1-C4)ハロアルキル、S(O)(C1-C4)ハロアルキル、S(O)2(C1-C4)ハロアルキル、(C1-C4)アルキル-S(O)2NH2、及び(C1-C4)ハロアルキル-S(O)2NH2からなる群から選択され;
(B) R2は、H、F、Cl、Br、I、CN、NH2、NO2、(C1-C4)アルキル、(C3-C6)シクロアルキル、(C2-C4)アルケニル、(C3-C6)シクロアルケニル、(C2-C4)アルキニル、(C1-C4)アルコキシ、(C1-C4)ハロアルキル、(C3-C6)ハロシクロアルキル、(C2-C4)ハロアルケニル、(C3-C6)ハロシクロアルケニル、(C1-C4)ハロアルコキシ、S(C1-C4)アルキル、S(O)(C1-C4)アルキル、S(O)2(C1-C4)アルキル、S(C1-C4)ハロアルキル、S(O)(C1-C4)ハロアルキル、S(O)2(C1-C4)ハロアルキル、(C1-C4)アルキル-S(O)2NH2、及び(C1-C4)ハロアルキル-S(O)2NH2からなる群から選択され;
(C) R3は、H、F、Cl、Br、I、CN、NH2、NO2、(C1-C4)アルキル、(C3-C6)シクロアルキル、(C2-C4)アルケニル、(C3-C6)シクロアルケニル、(C2-C4)アルキニル、(C1-C4)アルコキシ、(C1-C4)ハロアルキル、(C3-C6)ハロシクロアルキル、(C2-C4)ハロアルケニル、(C3-C6)ハロシクロアルケニル、(C1-C4)ハロアルコキシ、S(C1-C4)アルキル、S(O)(C1-C4)アルキル、S(O)2(C1-C4)アルキル、S(C1-C4)ハロアルキル、S(O)(C1-C4)ハロアルキル、S(O)2(C1-C4)ハロアルキル、(C1-C4)アルキル-S(O)2NH2、及び(C1-C4)ハロアルキル-S(O)2NH2からなる群から選択され;
(D) R4は、H、F、Cl、Br、I、CN、NH2、NO2、(C1-C4)アルキル、(C3-C6)シクロアルキル、(C2-C4)アルケニル、(C3-C6)シクロアルケニル、(C2-C4)アルキニル、(C1-C4)アルコキシ、(C1-C4)ハロアルキル、(C3-C6)ハロシクロアルキル、(C2-C4)ハロアルケニル、(C3-C6)ハロシクロアルケニル、(C1-C4)ハロアルコキシ、S(C1-C4)アルキル、S(O)(C1-C4)アルキル、S(O)2(C1-C4)アルキル、S(C1-C4)ハロアルキル、S(O)(C1-C4)ハロアルキル、S(O)2(C1-C4)ハロアルキル、(C1-C4)アルキル-S(O)2NH2、及び(C1-C4)ハロアルキル-S(O)2NH2からなる群から選択され;
(E) R5は、H、F、Cl、Br、I、CN、NH2、NO2、(C1-C4)アルキル、(C3-C6)シクロアルキル、(C2-C4)アルケニル、(C3-C6)シクロアルケニル、(C2-C4)アルキニル、(C1-C4)アルコキシ、(C1-C4)ハロアルキル、(C3-C6)ハロシクロアルキル、(C2-C4)ハロアルケニル、(C3-C6)ハロシクロアルケニル、(C1-C4)ハロアルコキシ、S(C1-C4)アルキル、S(O)(C1-C4)アルキル、S(O)2(C1-C4)アルキル、S(C1-C4)ハロアルキル、S(O)(C1-C4)ハロアルキル、S(O)2(C1-C4)ハロアルキル、(C1-C4)アルキル-S(O)2NH2、及び(C1-C4)ハロアルキル-S(O)2NH2からなる群から選択され;
(F) R6は、H及び(C1-C4)アルキルからなる群から選択され;
(G) R7は、H、F、Cl、Br、及びIからなる群から選択され;
(H) R8は、F、Cl、Br、及びIからなる群から選択され;
(I) R9は、H及び(C1-C4)アルキルからなる群から選択され;
(J) R10は、H、(C1-C4)アルキル、(C2-C4)アルケニル、(C1-C4)ハロアルキル、(C1-C4)アルキル(C1-C4)アルコキシ、C(=O)(C1-C4)アルキル、及び(C1-C4)アルコキシC(=O)(C1-C4)アルキルからなる群から選択され;
(K) R11は、H、F、Cl、Br、I、CN、NH2、NO2、(C1-C4)アルキル、(C3-C6)シクロアルキル、(C2-C4)アルケニル、(C3-C6)シクロアルケニル、(C2-C4)アルキニル、(C1-C4)アルコキシ、(C1-C4)ハロアルキル、(C3-C6)ハロシクロアルキル、(C2-C4)ハロアルケニル、(C3-C6)ハロシクロアルケニル、(C1-C4)ハロアルコキシ、S(C1-C4)アルキル、S(O)(C1-C4)アルキル、S(O)2(C1-C4)アルキル、S(C1-C4)ハロアルキル、S(O)(C1-C4)ハロアルキル、S(O)2(C1-C4)ハロアルキル、(C1-C4)アルキル-S(O)2NH2、及び(C1-C4)ハロアルキル-S(O)2NH2からなる群から選択され;
(L) R12は、H、F、Cl、Br、I、CN、NH2、NO2、(C1-C4)アルキル、(C3-C6)シクロアルキル、(C2-C4)アルケニル、(C3-C6)シクロアルケニル、(C2-C4)アルキニル、(C1-C4)アルコキシ、(C1-C4)ハロアルキル、(C3-C6)ハロシクロアルキル、(C2-C4)ハロアルケニル、(C3-C6)ハロシクロアルケニル、(C1-C4)ハロアルコキシ、S(C1-C4)アルキル、S(O)(C1-C4)アルキル、S(O)2(C1-C4)アルキル、S(C1-C4)ハロアルキル、S(O)(C1-C4)ハロアルキル、S(O)2(C1-C4)ハロアルキル、(C1-C4)アルキル-S(O)2NH2、及び(C1-C4)ハロアルキル-S(O)2NH2からなる群から選択され;
(M) R13は、H、F、Cl、Br、I、CN、NH2、NO2、(C1-C4)アルキル、(C3-C6)シクロアルキル、(C2-C4)アルケニル、(C3-C6)シクロアルケニル、(C2-C4)アルキニル、(C1-C4)アルコキシ、(C1-C4)ハロアルキル、(C3-C6)ハロシクロアルキル、(C2-C4)ハロアルケニル、(C3-C6)ハロシクロアルケニル、(C1-C4)ハロアルコキシ、S(C1-C4)アルキル、S(O)(C1-C4)アルキル、S(O)2(C1-C4)アルキル、S(C1-C4)ハロアルキル、S(O)(C1-C4)ハロアルキル、S(O)2(C1-C4)ハロアルキル、(C1-C4)アルキル-S(O)2NH2、及び(C1-C4)ハロアルキル-S(O)2NH2からなる群から選択され;
(N) R14は、H、F、Cl、Br、I、CN、NH2、NO2、(C1-C4)アルキル、(C3-C6)シクロアルキル、(C2-C4)アルケニル、(C3-C6)シクロアルケニル、(C2-C4)アルキニル、(C1-C4)アルコキシ、(C1-C4)ハロアルキル、(C3-C6)ハロシクロアルキル、(C2-C4)ハロアルケニル、(C3-C6)ハロシクロアルケニル、(C1-C4)ハロアルコキシ、S(C1-C4)アルキル、S(O)(C1-C4)アルキル、S(O)2(C1-C4)アルキル、S(C1-C4)ハロアルキル、S(O)(C1-C4)ハロアルキル、S(O)2(C1-C4)ハロアルキル、(C1-C4)アルキル-S(O)2NH2、及び(C1-C4)ハロアルキル-S(O)2NH2からなる群から選択され;
(O) R15は、H、(C1-C4)アルキル、(C2-C4)アルケニル、(C1-C4)ハロアルキル、(C1-C4)アルキル(C1-C4)アルコキシ、C(=O)(C1-C4)アルキル、及び(C1-C4)アルコキシC(=O)(C1-C4)アルキルからなる群から選択され;
(P) R16は、(C3-C8)シクロアルキル、アゼチジニル、2,5-ジオキソイミダゾリジニル、2,4-ジオキソ-1,3-ジアザスピロ[4.4]ノナニルイソオキサゾリジノニル、イミダゾリジノニル、イソオキサゾリジノニル、モルホリニル、オキサゾリジノニル、オキセタニル、ピペラジニル、ピペリジニル、ピラニル、ピロリジニル、ピロリジノニル、テトラヒドロフラニル、テトラヒドロピラニル、テトラヒドロチオフェニル、テトラヒドロチオフェニル-オキシド、テトラヒドロチオフェニル-ジオキシド、チエタニル、チエタニル-オキシド、チエタニル-ジオキシド、及びチオキソチアゾリジノニルからなる群から選択され、シクロアルキル、アゼチジニル、2,5-ジオキソイミダゾリジニル、2,4-ジオキソ-1,3-ジアザスピロ[4.4]ノナニルイソオキサゾリジノニル、イミダゾリジノニル、イソオキサゾリジノニル、モルホリニル、オキサゾリジノニル、オキセタニル、ピペラジニル、ピペリジニル、ピラニル、ピロリジニル、ピロリジノニル、テトラヒドロフラニル、テトラヒドロピラニル、テトラヒドロチオフェニル、テトラヒドロチオフェニル-オキシド、テトラヒドロチオフェニル-ジオキシド、チエタニル、チエタニル-オキシド、チエタニル-ジオキシド、及びチオキソチアゾリジノニルの各基は、H、F、Cl、Br、I、CN、NH2、NO2、
オキソ、(C1-C4)アルキル、(C1-C4)ハロアルキル、C(=O)O(C1-C4)アルキル、(C=O)NH(C1-C4)アルキル、(C=O)NH(C1-C4)ハロアルキル、C(=O)(C3-C6)シクロプロピル、C(=O)(C1-C4)ハロアルキル、C(=O)(C1-C4)アルキル(C1-C4)アルコキシ、及び(C1-C4)アルキル-モルホリニルから選択される1つ以上の置換基で任意選択的に置換されてもよく;
(Q) Q1及びQ2は、それぞれ独立にO及びSからなる群から選択される);
ならびに、式1の分子のN-オキシド、農学的に許容可能な酸付加塩、塩誘導体、溶媒和物、エステル誘導体、結晶多形体、同位体、分割立体異性体、及び互変異性体。
2D. シクロプロパンに結合したカルボキサミドとフェニルとがR,R配置である、詳細1Dに記載の分子。
3D. R1が、H、F、及びClからなる群から選択される、先行する詳細のいずれかに記載の分子(1D及び2Dの明確化)。
4D. R2が、H、F、Cl、Br、(C1-C4)アルキル、及び(C1-C4)ハロアルキルからなる群から選択される、先行する詳細のいずれかに記載の分子。
5D. R2が、H、F、Cl、Br、CH3、及びCF3からなる群から選択される、先行する詳細のいずれかに記載の分子。
6D. R3が、H、F、Cl、(C1-C4)アルキル、(C1-C4)ハロアルキル、及び(C1-C4)ハロアルコキシからなる群から選択される、先行する詳細のいずれかに記載の分子。
7D. R3が、H、F、Cl、CH3、CF3、及びOCF3からなる群から選択される、先行する詳細のいずれかに記載の分子。
8D. R4が、H、F、Cl、Br、(C1-C4)アルキル、及び(C1-C4)ハロアルキルからなる群から選択される、先行する詳細のいずれかに記載の分子。
9D. R4が、H、F、Cl、Br、CH3、及びCF3からなる群から選択される、先行する詳細のいずれかに記載の分子。
10D. R5が、H、F、及びClからなる群から選択される、先行する詳細のいずれかに記載の分子。
11D. R6がHである、先行する詳細のいずれかに記載の分子。
12D. R7がClである、先行する詳細のいずれかに記載の分子。
13D. R8がClである、先行する詳細のいずれかに記載の分子。
14D. R9がHである、先行する詳細のいずれかに記載の分子。
15D. R10がHである、先行する詳細のいずれかに記載の分子。
16D. R11がHである、先行する詳細のいずれかに記載の分子。
17D. R12がHである、先行する詳細のいずれかに記載の分子。
18D. R13が、H、Cl、及び(C1-C4)ハロアルキルからなる群から選択される、先行する詳細のいずれかに記載の分子。
19D. R13が、H、F、Cl、及びCF3からなる群から選択される、先行する詳細のいずれかに記載の分子。
20D. R14がHである、先行する詳細のいずれかに記載の分子。
21D. R15が、H及び(C1-C4)アルキルからなる群から選択される、先行する詳細のいずれかに記載の分子。
22D. R15が、H及びCH3からなる群から選択される、先行する詳細のいずれかに記載の分子。
23D. R16が、シクロプロピル、シクロブチル、シクロペンチル、シクロヘキシル、アゼチジニル、モルホリニル、オキセタニル、ピラニル、テトラヒドロチオフェニル、チエタニル、チエタニル-オキシド、及びチエタニル-ジオキシドからなる群から選択され、シクロプロピル、シクロブチル、シクロペンチル、シクロヘキシル、アゼチジニル、モルホリニル、オキセタニル、ピラニル、テトラヒドロチオフェニル、チエタニル、チエタニル-オキシド、及びチエタニル-ジオキシドの各基が、H、F、CN、C(=O)OC(CH3)3、及びC(=O)CF3からなる群から選択される1つ以上の置換基で任意選択的に置換され得る、先行する詳細のいずれかに記載の分子。
24D. Q1がOである、先行する詳細のいずれかに記載の分子。
25D. Q2がOである、先行する詳細のいずれかに記載の分子。
26D. 表2及び表P1の分子から選択される、先行する詳細のいずれかに記載の分子。
27D. 表2の分子F1〜F92、PF1〜PF9、PF12、PF14、PF18〜PF23、PF28〜PF34、PF36、PF37、及びPF41〜PF45から選択される、先行する詳細のいずれかに記載の分子。
28D. 担体をさらに含む、分子に関連した先行する詳細(1D〜27Dの明確化のため以下「分子詳細」)のいずれか1つに記載の分子を含む組成物。
29D. 活性成分をさらに含む、先行する分子詳細のいずれか1つに記載の分子を含む組成物。
30D. 殺ダニ剤、殺藻剤、摂食阻害剤、殺鳥剤、殺菌剤、鳥忌避剤、化学不妊剤、殺真菌剤、除草剤毒性緩和剤、除草剤、昆虫誘引剤、昆虫忌避剤、殺虫剤、哺乳動物忌避剤、交尾阻害剤、軟体動物駆除剤、殺線虫剤、植物活性剤、植物成長調節剤、殺鼠剤、相乗剤、及び抗ウイルス剤から選択される活性成分をさらに含む、先行する分子詳細のいずれか1つに記載の分子を含む組成物。
31D. AIGAから選択される活性成分をさらに含む、先行する分子詳細のいずれか1つに記載の分子を含む組成物。
32D. AI-1をさらに含む、先行する分子詳細のいずれか1つに記載の分子を含む組成物。
33D. AI-2をさらに含む、先行する分子詳細のいずれか1つに記載の分子を含む組成物。
34D. ロチラネル(Lotilaner)をさらに含む、先行する分子詳細のいずれか1つに記載の分子を含む組成物。
35D. 表Aから選択される分子をさらに含む、先行する分子詳細のいずれか1つに記載の分子を含む組成物。
36D. AIGA-2から選択される活性成分をさらに含む、先行する分子詳細のいずれか1つに記載の分子を含む組成物。
37D. バイオ農薬をさらに含む、先行する分子詳細のいずれか1つに記載の分子を含む組成物。
38D. アセチルコリンエステラーゼ(AChE)阻害剤からの活性成分をさらに含む、先行する分子詳細のいずれか1つに記載の分子を含む組成物。
39D. GABA作動性クロライドチャネルアンタゴニストからの活性成分をさらに含む、先行する分子詳細のいずれか1つに記載の分子を含む組成物。
40D. ナトリウムチャネルモジュレータからの活性成分をさらに含む、先行する分子詳細のいずれか1つに記載の分子を含む組成物。
41D. ニコチン性アセチルコリン受容体(nAChR)アゴニストからの活性成分をさらに含む、先行する分子詳細のいずれか1つに記載の分子を含む組成物。
42D. ニコチン性アセチルコリン受容体(nAChR)アロステリック活性化因子からの活性成分をさらに含む、先行する分子詳細のいずれか1つに記載の分子を含む組成物。
43D. クロライドチャネル活性化因子からの活性成分をさらに含む、先行する分子詳細のいずれか1つに記載の分子を含む組成物。
44D. 幼若ホルモン模倣物からの活性成分をさらに含む、先行する分子詳細のいずれか1つに記載の分子を含む組成物。
45D. 多種非特異性(多部位)阻害剤からの活性成分をさらに含む、先行する分子詳細のいずれか1つに記載の分子を含む組成物。
46D. 弦音器官のモジュレータからの活性成分をさらに含む、先行する分子詳細のいずれか1つに記載の分子を含む組成物。
47D. ダニ増殖阻害剤からの活性成分をさらに含む、先行する分子詳細のいずれか1つに記載の分子を含む組成物。
48D. 昆虫中腸膜の微生物撹乱剤からの活性成分をさらに含む、先行する分子詳細のいずれか1つに記載の分子を含む組成物。
49D. ミトコンドリアATP合成酵素阻害剤からの活性成分をさらに含む、先行する分子
詳細のいずれか1つに記載の分子を含む組成物。
50D. プロトン勾配の乱れを介した酸化的リン酸化の脱共役剤からの活性成分をさらに含む、先行する分子詳細のいずれか1つに記載の分子を含む組成物。
51D. ニコチン性アセチルコリン受容体(nAChR)チャネル遮断剤からの活性成分をさらに含む、先行する分子詳細のいずれか1つに記載の分子を含む組成物。
52D. キチン生合成阻害剤、タイプ0からの活性成分をさらに含む、先行する分子詳細のいずれか1つに記載の分子を含む組成物。
53D. キチン生合成阻害剤、タイプ1からの活性成分をさらに含む、先行する分子詳細のいずれか1つに記載の分子を含む組成物。
54D. 双翅目の脱皮撹乱剤からの活性成分をさらに含む、先行する分子詳細のいずれか1つに記載の分子を含む組成物。
55D. エクジソン受容体アゴニストからの活性成分をさらに含む、先行する分子詳細のいずれか1つに記載の分子を含む組成物。
56D. オクトパミン受容体アゴニストからの活性成分をさらに含む、先行する分子詳細のいずれか1つに記載の分子を含む組成物。
57D. ミトコンドリア複合体III電子伝達阻害剤からの活性成分をさらに含む、先行する分子詳細のいずれか1つに記載の分子を含む組成物。
58D. ミトコンドリア複合体I電子伝達阻害剤からの活性成分をさらに含む、先行する分子詳細のいずれか1つに記載の分子を含む組成物。
59D. 電位依存性ナトリウムチャネル遮断剤からの活性成分をさらに含む、先行する分子詳細のいずれか1つに記載の分子を含む組成物。
60D. アセチルCoAカルボキシラーゼ阻害剤からの活性成分をさらに含む、先行する分子詳細のいずれか1つに記載の分子を含む組成物。
61D. ミトコンドリア複合体IV電子伝達阻害剤からの活性成分をさらに含む、先行する分子詳細のいずれか1つに記載の分子を含む組成物。
62D. ミトコンドリア複合体II電子伝達阻害剤からの活性成分をさらに含む、先行する分子詳細のいずれか1つに記載の分子を含む組成物。
63D. リアノジン受容体モジュレータからの活性成分をさらに含む、先行する分子詳細のいずれか1つに記載の分子を含む組成物。
64D. 群UNからの活性成分をさらに含む、先行する分子詳細のいずれか1つに記載の分子を含む組成物。
65D. 害虫を防除するプロセスであって、ある領域に前記分子詳細のいずれか1つに記載の分子の農薬有効量を適用することを含む前記プロセス。
66D. 害虫を防除するプロセスであって、ある領域に詳細28D〜詳細64Dのいずれか1つに記載の組成物の農薬有効量を適用することを含む前記プロセス。
67D. 前記害虫が、アリ、アブラムシ、ナンキンムシ、甲虫、シミ、毛虫、ゴキブリ、コオロギ、ハサミムシ、ノミ、ハエ、バッタ、地虫、ヨコバイ、シラミ、イナゴ、ウジ、ダニ、線虫、ウンカ、キジラミ、ハバチ、カイガラムシ、セイヨウシミ、ナメクジ、カタツムリ、クモ、トビムシ、カメムシ、結合類、シロアリ、アザミウマ、マダニ、ジガバチ、コナジラミ、及びハリガネムシからなる群から選択される、詳細65Dまたは詳細66Dのいずれか1つに記載のプロセス。
68D. 前記害虫が樹液を食する害虫である、詳細65Dまたは詳細66Dのいずれか1つに記載のプロセス。
69D. 前記害虫が、アブラムシ、ヨコバイ、ガ、カイガラムシ、アザミウマ、キジラミ、コナカイガラムシ、カメムシ、及びコナジラミからなる群から選択される、詳細65Dまたは詳細66Dのいずれか1つに記載のプロセス。
70D. 前記害虫がシラミ目及び半翅目からなる群から選択される、詳細65Dまたは詳細66Dのいずれか1つに記載のプロセス。
71D. 前記害虫が、アウラカスピス属種(Aulacaspis spp.)、アフロフォラ属種(Aphrophora spp.)、アフィス属種(Aphis spp.)、ベミシア属種(Bemisia spp.)、コッ
クス属種(Coccus spp.)、エウシスツス属種(Euschistus spp.)、リグス属種(Lygus spp.)、マクロシフム属種(Macrosiphum spp.)、ネザラ属種(Nezara spp.)、及びロパロシフム属種(Rhopalosiphum spp.)からなる群から選択される、詳細65Dまたは詳細66Dのいずれか1つに記載のプロセス。
72D. 前記害虫が咀嚼害虫である、詳細65Dまたは詳細66Dのいずれか1つに記載のプロセス。
73D. 前記害虫が毛虫、甲虫、バッタ、及びイナゴからなる群から選択される、詳細65Dまたは詳細66Dのいずれか1つに記載のプロセス。
74D. 前記害虫が鞘翅目及び鱗翅目からなる群から選択される、詳細65Dまたは詳細66Dのいずれか1つに記載のプロセス。
75D. 前記害虫が、アントノムス属種(Anthonomus spp.)、セロトマ属種(Cerotoma
spp.)、カエトクネマ属種(Chaetocnema spp.)、コラスピス属種(Colaspis spp.)、シクロセファラ属種(Cyclocephala spp.)、ジアブロチカ属種(Diabrotica spp.)、ヒペラ属種(Hypera spp.)、フィロファガ属種( Phyllophaga spp.)、フィロトレタ属種(Phyllotreta spp.)、スフェノフォルス属種(Sphenophorus spp.)、シトフィルス属種(Sitophilus spp.)からなる群から選択される、詳細65Dまたは詳細66Dのいずれか1つに記載のプロセス。
Claims (16)
- 以下の式を有する分子
(A) R1は、H、F、Cl、Br、I、CN、NH2、NO2、(C1-C4)アルキル、(C3-C6)シクロアルキル、(C2-C4)アルケニル、(C3-C6)シクロアルケニル、(C2-C4)アルキニル、(C1-C4)アルコキシ、(C1-C4)ハロアルキル、(C3-C6)ハロシクロアルキル、(C2-C4)ハロアルケニル、(C3-C6)ハロシクロアルケニル、(C1-C4)ハロアルコキシ、S(C1-C4)アルキル、S(O)(C1-C4)アルキル、S(O)2(C1-C4)アルキル、S(C1-C4)ハロアルキル、S(O)(C1-C4)ハロアルキル、S(O)2(C1-C4)ハロアルキル、(C1-C4)アルキル-S(O)2NH2、及び(C1-C4)ハロアルキル-S(O)2NH2
からなる群から選択され;
(B) R2は、H、F、Cl、Br、I、CN、NH2、NO2、(C1-C4)アルキル、(C3-C6)シクロアルキル、(C2-C4)アルケニル、(C3-C6)シクロアルケニル、(C2-C4)アルキニル、(C1-C4)アルコキシ、(C1-C4)ハロアルキル、(C3-C6)ハロシクロアルキル、(C2-C4)ハロアルケニル、(C3-C6)ハロシクロアルケニル、(C1-C4)ハロアルコキシ、S(C1-C4)アルキル、S(O)(C1-C4)アルキル、S(O)2(C1-C4)アルキル、S(C1-C4)ハロアルキル、S(O)(C1-C4)ハロアルキル、S(O)2(C1-C4)ハロアルキル、(C1-C4)アルキル-S(O)2NH2、及び(C1-C4)ハロアルキル-S(O)2NH2
からなる群から選択され;
(C) R3は、H、F、Cl、Br、I、CN、NH2、NO2、(C1-C4)アルキル、(C3-C6)シクロアルキル、(C2-C4)アルケニル、(C3-C6)シクロアルケニル、(C2-C4)アルキニル、(C1-C4)アルコキシ、(C1-C4)ハロアルキル、(C3-C6)ハロシクロアルキル、(C2-C4)ハロアルケニル、(C3-C6)ハロシクロアルケニル、(C1-C4)ハロアルコキシ、S(C1-C4)アルキル、S(O)(C1-C4)アルキル、S(O)2(C1-C4)アルキル、S(C1-C4)ハロアルキル、S(O)(C1-C4)ハロアルキル、S(O)2(C1-C4)ハロアルキル、(C1-C4)アルキル-S(O)2NH2、及び(C1-C4)ハロアルキル-S(O)2NH2
からなる群から選択され;
(D) R4は、H、F、Cl、Br、I、CN、NH2、NO2、(C1-C4)アルキル、(C3-C6)シクロアルキル、(C2-C4)アルケニル、(C3-C6)シクロアルケニル、(C2-C4)アルキニル、(C1-C4)アルコキシ、(C1-C4)ハロアルキル、(C3-C6)ハロシクロアルキル、(C2-C4)ハロアルケニル、(C3-C6)ハロシクロアルケニル、(C1-C4)ハロアルコキシ、S(C1-C4)アルキル、S(O)(C1-C4)アルキル、S(O)2(C1-C4)アルキル、S(C1-C4)ハロアルキル、S(O)(C1-C4)ハロアルキル、S(O)2(C1-C4)ハロアルキル、(C1-C4)アルキル-S(O)2NH2、及び(C1-C4)ハロアルキル-S(O)2NH2
からなる群から選択され;
(E) R5は、H、F、Cl、Br、I、CN、NH2、NO2、(C1-C4)アルキル、(C3-C6)シクロアルキル、(C2-C4)アルケニル、(C3-C6)シクロアルケニル、(C2-C4)アルキニル、(C1-C4)アルコキシ、(C1-C4)ハロアルキル、(C3-C6)ハロシクロアルキル、(C2-C4)ハロアルケニル、(C3-C6)ハロシクロアルケニル、(C1-C4)ハロアルコキシ、S(C1-C4)アルキル、S(O)(C1-C4)アルキル、S(O)2(C1-C4)アルキル、S(C1-C4)ハロアルキル、S(O)(C1-C4)ハロアルキル、S(O)2(C1-C4)ハロアルキル、(C1-C4)アルキル-S(O)2NH2、及び(C1-C4)ハロアルキル-S(O)2NH2
からなる群から選択され;
(F) R6は、H及び(C1-C4)アルキルからなる群から選択され;
(G) R7は、H、F、Cl、Br、及びIからなる群から選択され;
(H) R8は、F、Cl、Br、及びIからなる群から選択され;
(I) R9は、H及び(C1-C4)アルキルからなる群から選択され;
(J) R10は、H、(C1-C4)アルキル、(C2-C4)アルケニル、(C1-C4)ハロアルキル、(C1-C4)アルキル(C1-C4)アルコキシ、C(=O)(C1-C4)アルキル、及び(C1-C4)アルコキシC(=O)(C1-C4)アルキルからなる群から選択され;
(K) R11は、H、F、Cl、Br、I、CN、NH2、NO2、(C1-C4)アルキル、(C3-C6)シクロアルキル、(C2-C4)アルケニル、(C3-C6)シクロアルケニル、(C2-C4)アルキニル、(C1-C4)アルコキシ、(C1-C4)ハロアルキル、(C3-C6)ハロシクロアルキル、(C2-C4)ハロアルケニル、(C3-C6)ハロシクロアルケニル、(C1-C4)ハロアルコキシ、S(C1-C4)アルキル、S(O)(C1-C4)アルキル、S(O)2(C1-C4)アルキル、S(C1-C4)ハロアルキル、S(O)(C1-C4)ハロアルキル、S(O)2(C1-C4)ハロアルキル、(C1-C4)アルキル-S(O)2NH2、及び(C1-C4)ハロアルキル-S(O)2NH2からなる群から選択され;
(L) R12は、H、F、Cl、Br、I、CN、NH2、NO2、(C1-C4)アルキル、(C3-C6)シクロアルキル、(C2-C4)アルケニル、(C3-C6)シクロアルケニル、(C2-C4)アルキニル、(C1-C4)アルコキシ、(C1-C4)ハロアルキル、(C3-C6)ハロシクロアルキル、(C2-C4)ハロアルケニル、(C3-C6)ハロシクロアルケニル、(C1-C4)ハロアルコキシ、S(C1-C4)アルキル、S(O)(C1-C4)アルキル、S(O)2(C1-C4)アルキル、S(C1-C4)ハロアルキル、S(O)(C1-C4)ハロアルキル、S(O)2(C1-C4)ハロアルキル、(C1-C4)アルキル-S(O)2NH2、及び(C1-C4)ハロアルキル-S(O)2NH2からなる群から選択され;
(M) R13は、H、F、Cl、Br、I、CN、NH2、NO2、(C1-C4)アルキル、(C3-C6)シクロアルキル、(C2-C4)アルケニル、(C3-C6)シクロアルケニル、(C2-C4)アルキニル、(C1-C4)アルコキシ、(C1-C4)ハロアルキル、(C3-C6)ハロシクロアルキル、(C2-C4)ハロアルケニル、(C3-C6)ハロシクロアルケニル、(C1-C4)ハロアルコキシ、S(C1-C4)アルキル、S(O)(C1-C4)アルキル、S(O)2(C1-C4)アルキル、S(C1-C4)ハロアルキル、S(O)(C1-C4)ハロアルキル、S(O)2(C1-C4)ハロアルキル、(C1-C4)アルキル-S(O)2NH2、及び(C1-C4)ハロアルキル-S(O)2NH2からなる群から選択され;
(N) R14は、H、F、Cl、Br、I、CN、NH2、NO2、(C1-C4)アルキル、(C3-C6)シクロアルキル、(C2-C4)アルケニル、(C3-C6)シクロアルケニル、(C2-C4)アルキニル、(C1-C4)アルコキシ、(C1-C4)ハロアルキル、(C3-C6)ハロシクロアルキル、(C2-C4)ハロアルケニル、(C3-C6)ハロシクロアルケニル、(C1-C4)ハロアルコキシ、S(C1-C4)アルキル、S(O)(C1-C4)アルキル、S(O)2(C1-C4)アルキル、S(C1-C4)ハロアルキル、S(O)(C1-C4)ハロアルキル、S(O)2(C1-C4)ハロアルキル、(C1-C4)アルキル-S(O)2NH2、及び(C1-C4)ハロアルキル-S(O)2NH2からなる群から選択され;
(O) R15は、H、(C1-C4)アルキル、(C2-C4)アルケニル、(C1-C4)ハロアルキル、(C1-C4)アルキル(C1-C4)アルコキシ、C(=O)(C1-C4)アルキル、及び(C1-C4)アルコキシC(=O)(C1-C4)アルキルからなる群から選択され;
(P) R16は、(C3-C8)シクロアルキル、アゼチジニル、2,5-ジオキソイミダゾリジニル、2,4-ジオキソ-1,3-ジアザスピロ[4.4]ノナニルイソオキサゾリジノニル、イミダゾリジノニル、イソオキサゾリジノニル、モルホリニル、オキサゾリジノニル、オキセタニル、ピペラジニル、ピペリジニル、ピラニル、ピロリジニル、ピロリジノニル、テトラヒドロフラニル、テトラヒドロピラニル、テトラヒドロチオフェニル、テトラヒドロチオフェニル-オキシド、テトラヒドロチオフェニル-ジオキシド、チエタニル、チエタニル-オキシド、チエタニル-ジオキシド、及びチオキソチアゾリジノニルからなる群から選択され、シクロアルキル、アゼチジニル、2,5-ジオキソイミダゾリジニル、2,4-ジオキソ-1,3-ジアザスピロ[4.4]ノナニルイソオキサゾリジノニル、イミダゾリジノニル、イソオキサゾリジノニル、モルホリニル、オキサゾリジノニル、オキセタニル、ピペラジニル、ピペリジニル、ピラニル、ピロリジニル、ピロリジノニル、テトラヒドロフラニル、テトラヒドロピラニル、テトラヒドロチオフェニル、テトラヒドロチオフェニル-オキシド、テトラヒドロチオフェニル-ジオキシド、チエタニル、チエタニル-オキシド、チエタニル-ジオキシド、及びチオキソチアゾリジノニルの各基は、F、Cl、Br、I、CN、NH2、NO2、オキソ、(C1-C4)アルキル、(C1-C4)ハロアルキル、C(=O)O(C1-C4)アルキル、(C=O)NH(C1-C4)アルキル、(C=O)NH(C1-C4)ハロアルキル、C(=O)(C3-C6)シクロアルキル、C(=O)(C1-C4)ハロアルキル、C(=O)(C1-C4)アルキル(C1-C4)アルコキシ、及び(C1-C4)アルキル-モルホリニルからなる群から選択される1つ以上の置換基で任意選択的に置換されてもよく;
(Q) Q1及びQ2は、それぞれ独立にO及びSからなる群から選択される);ならびに式1の分子のN-オキシド、農学的に許容可能な酸付加塩、溶媒和物、結晶多形体、同位体、分割立体異性体、及び互変異性体。 - R1が、H、F、及びClからなる群から選択される、請求項1に記載の分子。
- R2が、H、F、Cl、Br、CH3、及びCF3からなる群から選択される、請求項1または2に記載の分子。
- R3が、H、F、Cl、CH3、CF3、及びOCF3からなる群から選択される、請求項1〜3のいずれかに記載の分子。
- R4が、H、F、Cl、Br、CH3、及びCF3からなる群から選択される、請求項1〜4のいずれかに記載の分子。
- R5が、H、F、及びClからなる群から選択される、請求項1に記載の分子。
- R7及びR8がClである、請求項1〜6のいずれかに記載の分子。
- R13が、H、Cl、及びCF3からなる群から選択される、請求項1〜7のいずれかに記載の
分子。 - R15が、H及びCH3からなる群から選択される、請求項1〜8のいずれかに記載の分子。
- R16が、シクロプロピル、シクロブチル、シクロペンチル、シクロヘキシル、アゼチジニル、モルホリニル、オキセタニル、ピラニル、テトラヒドロチオフェニル、チエタニル、チエタニル-オキシド、及びチエタニル-ジオキシドからなる群から選択され、
シクロプロピル、シクロブチル、シクロペンチル、シクロヘキシル、アゼチジニル、モルホリニル、オキセタニル、ピラニル、テトラヒドロチオフェニル、チエタニル、チエタニル-オキシド、及びチエタニル-ジオキシドの各基が、F、CN、C(=O)OC(CH3)3、及びC(=O)CF3からなる群から選択される1つ以上の置換基で任意選択的に置換され得る、請求項1〜9のいずれかに記載の分子。 - (A) R1が、H、F、及びClからなる群から選択され;
(B) R2が、H、F、Cl、Br、CH3、及びCF3からなる群から選択され;
(C) R3が、H、F、Cl、CH3、及びCF3、OCF3からなる群から選択され;
(D) R4が、H、F、Cl、Br、CH3、及びCF3からなる群から選択され;
(E) R5がHであり;
(F) R6がHであり;
(G) R7が、Cl及びBrからなる群から選択され;
(H) R8が、Cl及びBrからなる群から選択され;
(I) R9、R10、R11、及びR12がHであり;
(J) R13が、H、F、Cl、及びCF3からなる群から選択され;
(K) R14がHであり;
(L) R15が、H及びCH3からなる群から選択され;
(M) R16が、(C3-C8)シクロアルキル、アゼチジニル、モルホリニル、オキセタニル、ピラニル、テトラヒドロチオフェニル、チエタニル、チエタニル-オキシド、及びチエタニ-ジオキシドからなる群から選択され、シクロアルキル、アゼチジニル、モルホリニル、オキセタニル、ピラニル、テトラヒドロチオフェニル、チエタニル、チエタニル-オキシド、及びチエタニル-ジオキシドの各基が、F、CN、C(=O)O(C1-C4)アルキル、C(=O)(C3-C6)シクロアルキル、C(=O)(C1-C4)ハロアルキル、及びC(=O)(C1-C4)アルキル(C1-C4)アルコキシからなる群から選択される1つ以上の置換基で任意選択的に置換されてもよく;
(N) Q1及びQ2がOである、請求項1に記載の分子。 - 請求項1から請求項13のいずれか1項に記載の分子と、活性成分とを含む組成物。
- 害虫を防除するプロセスであって、ヒト以外のある領域に、農薬有効量の、請求項1から請求項13のいずれか1項に記載の分子を適用することを含む前記プロセス。
- 害虫を防除するプロセスであって、ヒト以外のある領域に、農薬有効量の、有効成分としての請求項1から請求項13のいずれか1項に記載の分子を含んでなる組成物を適用することを含む前記プロセス。
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JP2020183417A (ja) * | 2015-04-17 | 2020-11-12 | ダウ アグロサイエンシィズ エルエルシー | 農薬の効用を有する分子ならびに関連する中間体、組成物及びプロセス |
JP7101728B2 (ja) | 2015-04-17 | 2022-07-15 | コルテバ アグリサイエンス エルエルシー | 農薬の効用を有する分子ならびに関連する中間体、組成物及びプロセス |
JP2022130674A (ja) * | 2015-04-17 | 2022-09-06 | コルテバ アグリサイエンス エルエルシー | 農薬の効用を有する分子ならびに関連する中間体、組成物及びプロセス |
JP7329108B2 (ja) | 2015-04-17 | 2023-08-17 | コルテバ アグリサイエンス エルエルシー | 農薬の効用を有する分子ならびに関連する中間体、組成物及びプロセス |
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