JPWO2018207847A1 - ピラゾール−3−カルボン酸アミド誘導体及び有害生物防除剤 - Google Patents
ピラゾール−3−カルボン酸アミド誘導体及び有害生物防除剤 Download PDFInfo
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- JPWO2018207847A1 JPWO2018207847A1 JP2019517679A JP2019517679A JPWO2018207847A1 JP WO2018207847 A1 JPWO2018207847 A1 JP WO2018207847A1 JP 2019517679 A JP2019517679 A JP 2019517679A JP 2019517679 A JP2019517679 A JP 2019517679A JP WO2018207847 A1 JPWO2018207847 A1 JP WO2018207847A1
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- cycloalkyl
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- BNYCHCAYYYRJSH-UHFFFAOYSA-N 1h-pyrazole-5-carboxamide Chemical class NC(=O)C1=CC=NN1 BNYCHCAYYYRJSH-UHFFFAOYSA-N 0.000 title claims abstract description 29
- 239000000575 pesticide Substances 0.000 title claims description 7
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 244
- 241000607479 Yersinia pestis Species 0.000 claims abstract description 80
- 239000000203 mixture Substances 0.000 claims abstract description 66
- 150000003839 salts Chemical class 0.000 claims abstract description 59
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 45
- 239000004480 active ingredient Substances 0.000 claims abstract description 25
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 20
- 230000000361 pesticidal effect Effects 0.000 claims abstract description 20
- 125000005843 halogen group Chemical group 0.000 claims abstract description 18
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims abstract description 11
- -1 hydroxyimino Chemical group 0.000 claims description 1016
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 72
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- 238000000034 method Methods 0.000 claims description 30
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 29
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 27
- 125000003277 amino group Chemical group 0.000 claims description 27
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims description 26
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- 125000004741 (C1-C6) haloalkylsulfonyl group Chemical group 0.000 claims description 19
- 125000004432 carbon atom Chemical group C* 0.000 claims description 17
- 125000004738 (C1-C6) alkyl sulfinyl group Chemical group 0.000 claims description 16
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 16
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims description 16
- 241000196324 Embryophyta Species 0.000 claims description 15
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 14
- KOPFEFZSAMLEHK-UHFFFAOYSA-N 1h-pyrazole-5-carboxylic acid Chemical class OC(=O)C=1C=CNN=1 KOPFEFZSAMLEHK-UHFFFAOYSA-N 0.000 claims description 14
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 14
- 229910052757 nitrogen Inorganic materials 0.000 claims description 14
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 12
- 125000004844 (C1-C6) alkoxyimino group Chemical group 0.000 claims description 12
- 125000004749 (C1-C6) haloalkylsulfinyl group Chemical group 0.000 claims description 12
- 125000006771 (C1-C6) haloalkylthio group Chemical group 0.000 claims description 12
- 125000000304 alkynyl group Chemical group 0.000 claims description 12
- 230000001276 controlling effect Effects 0.000 claims description 12
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 11
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 11
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- 125000006643 (C2-C6) haloalkenyl group Chemical group 0.000 claims description 9
- 125000006644 (C2-C6) haloalkynyl group Chemical group 0.000 claims description 9
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 9
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- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 8
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 8
- 229910052717 sulfur Inorganic materials 0.000 claims description 8
- 239000004094 surface-active agent Substances 0.000 claims description 8
- 125000004682 aminothiocarbonyl group Chemical group NC(=S)* 0.000 claims description 6
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- 125000004434 sulfur atom Chemical group 0.000 claims description 5
- 125000004008 6 membered carbocyclic group Chemical group 0.000 claims description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
- 125000005842 heteroatom Chemical group 0.000 claims description 4
- 125000000623 heterocyclic group Chemical group 0.000 claims description 4
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- 125000004487 4-tetrahydropyranyl group Chemical group [H]C1([H])OC([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 2
- 238000009395 breeding Methods 0.000 claims description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 2
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- 125000004043 oxo group Chemical group O=* 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 125000005400 pyridylcarbonyl group Chemical group N1=C(C=CC=C1)C(=O)* 0.000 claims description 2
- 125000001188 haloalkyl group Chemical group 0.000 abstract description 11
- 230000000694 effects Effects 0.000 abstract description 10
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- 125000000217 alkyl group Chemical group 0.000 description 57
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- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 36
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- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 30
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 30
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- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 26
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 26
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- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 24
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- 238000004519 manufacturing process Methods 0.000 description 24
- 239000005589 Oxasulfuron Substances 0.000 description 23
- IOXAXYHXMLCCJJ-UHFFFAOYSA-N oxetan-3-yl 2-[(4,6-dimethylpyrimidin-2-yl)carbamoylsulfamoyl]benzoate Chemical compound CC1=CC(C)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)C(=O)OC2COC2)=N1 IOXAXYHXMLCCJJ-UHFFFAOYSA-N 0.000 description 23
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 21
- 241000254173 Coleoptera Species 0.000 description 20
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- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 20
- 239000000243 solution Substances 0.000 description 20
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 19
- 239000002253 acid Substances 0.000 description 19
- 239000002585 base Substances 0.000 description 18
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 17
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 16
- 239000003054 catalyst Substances 0.000 description 16
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 16
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- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 14
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 14
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 14
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- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 14
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- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
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- 239000004408 titanium dioxide Substances 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- OBZIQQJJIKNWNO-UHFFFAOYSA-N tolclofos-methyl Chemical compound COP(=S)(OC)OC1=C(Cl)C=C(C)C=C1Cl OBZIQQJJIKNWNO-UHFFFAOYSA-N 0.000 description 1
- RSOBJVBYZCMJOS-CYBMUJFWSA-N tolprocarb Chemical compound FC(F)(F)COC(=O)N[C@@H](C(C)C)CNC(=O)C1=CC=C(C)C=C1 RSOBJVBYZCMJOS-CYBMUJFWSA-N 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- HYVWIQDYBVKITD-UHFFFAOYSA-N tolylfluanid Chemical compound CN(C)S(=O)(=O)N(SC(F)(Cl)Cl)C1=CC=C(C)C=C1 HYVWIQDYBVKITD-UHFFFAOYSA-N 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- BAZVSMNPJJMILC-UHFFFAOYSA-N triadimenol Chemical compound C1=NC=NN1C(C(O)C(C)(C)C)OC1=CC=C(Cl)C=C1 BAZVSMNPJJMILC-UHFFFAOYSA-N 0.000 description 1
- NKNFWVNSBIXGLL-UHFFFAOYSA-N triazamate Chemical compound CCOC(=O)CSC1=NC(C(C)(C)C)=NN1C(=O)N(C)C NKNFWVNSBIXGLL-UHFFFAOYSA-N 0.000 description 1
- AMFGTOFWMRQMEM-UHFFFAOYSA-N triazophos Chemical compound N1=C(OP(=S)(OCC)OCC)N=CN1C1=CC=CC=C1 AMFGTOFWMRQMEM-UHFFFAOYSA-N 0.000 description 1
- IQGKIPDJXCAMSM-UHFFFAOYSA-N triazoxide Chemical compound N=1C2=CC=C(Cl)C=C2[N+]([O-])=NC=1N1C=CN=C1 IQGKIPDJXCAMSM-UHFFFAOYSA-N 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 1
- REEQLXCGVXDJSQ-UHFFFAOYSA-N trichlopyr Chemical compound OC(=O)COC1=NC(Cl)=C(Cl)C=C1Cl REEQLXCGVXDJSQ-UHFFFAOYSA-N 0.000 description 1
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- QFNFRZHOXWNWAQ-UHFFFAOYSA-N triclopyricarb Chemical compound COC(=O)N(OC)C1=CC=CC=C1COC1=NC(Cl)=C(Cl)C=C1Cl QFNFRZHOXWNWAQ-UHFFFAOYSA-N 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- ONCZDRURRATYFI-TVJDWZFNSA-N trifloxystrobin Chemical compound CO\N=C(\C(=O)OC)C1=CC=CC=C1CO\N=C(/C)C1=CC=CC(C(F)(F)F)=C1 ONCZDRURRATYFI-TVJDWZFNSA-N 0.000 description 1
- HSMVPDGQOIQYSR-KGENOOAVSA-N triflumizole Chemical compound C1=CN=CN1C(/COCCC)=N/C1=CC=C(Cl)C=C1C(F)(F)F HSMVPDGQOIQYSR-KGENOOAVSA-N 0.000 description 1
- XAIPTRIXGHTTNT-UHFFFAOYSA-N triflumuron Chemical compound C1=CC(OC(F)(F)F)=CC=C1NC(=O)NC(=O)C1=CC=CC=C1Cl XAIPTRIXGHTTNT-UHFFFAOYSA-N 0.000 description 1
- ZSDSQXJSNMTJDA-UHFFFAOYSA-N trifluralin Chemical compound CCCN(CCC)C1=C([N+]([O-])=O)C=C(C(F)(F)F)C=C1[N+]([O-])=O ZSDSQXJSNMTJDA-UHFFFAOYSA-N 0.000 description 1
- IMEVJVISCHQJRM-UHFFFAOYSA-N triflusulfuron-methyl Chemical group COC(=O)C1=CC=CC(C)=C1S(=O)(=O)NC(=O)NC1=NC(OCC(F)(F)F)=NC(N(C)C)=N1 IMEVJVISCHQJRM-UHFFFAOYSA-N 0.000 description 1
- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 description 1
- RROQIUMZODEXOR-UHFFFAOYSA-N triforine Chemical compound O=CNC(C(Cl)(Cl)Cl)N1CCN(C(NC=O)C(Cl)(Cl)Cl)CC1 RROQIUMZODEXOR-UHFFFAOYSA-N 0.000 description 1
- 241000701366 unidentified nuclear polyhedrosis viruses Species 0.000 description 1
- 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- DBXFMOWZRXXBRN-LWKPJOBUSA-N valifenalate Chemical compound CC(C)OC(=O)N[C@@H](C(C)C)C(=O)NC(CC(=O)OC)C1=CC=C(Cl)C=C1 DBXFMOWZRXXBRN-LWKPJOBUSA-N 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 239000010455 vermiculite Substances 0.000 description 1
- 229910052902 vermiculite Inorganic materials 0.000 description 1
- 235000019354 vermiculite Nutrition 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 235000020234 walnut Nutrition 0.000 description 1
- 239000004562 water dispersible granule Substances 0.000 description 1
- 229920003169 water-soluble polymer Polymers 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- WCJYTPVNMWIZCG-UHFFFAOYSA-N xylylcarb Chemical compound CNC(=O)OC1=CC=C(C)C(C)=C1 WCJYTPVNMWIZCG-UHFFFAOYSA-N 0.000 description 1
- DUBNHZYBDBBJHD-UHFFFAOYSA-L ziram Chemical compound [Zn+2].CN(C)C([S-])=S.CN(C)C([S-])=S DUBNHZYBDBBJHD-UHFFFAOYSA-L 0.000 description 1
- 229930007845 β-thujaplicin Natural products 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
- A61K31/4439—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. omeprazole
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/10—Anthelmintics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/14—Ectoparasiticides, e.g. scabicides
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Tropical Medicine & Parasitology (AREA)
- General Chemical & Material Sciences (AREA)
- Dentistry (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Engineering & Computer Science (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Epidemiology (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Catching Or Destruction (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Description
nは、0又は1の整数を示し、
Xは、酸素原子又は硫黄原子を示し、
R1、R2、R3、R4及びR5は、各々独立して水素原子、ハロゲン原子、C1〜C6アルキル基、C1〜C6ハロアルキル基、C1〜C6アルコキシ基、C1〜C6ハロアルコキシ基、C3〜C6シクロアルキル基、C1〜C6アルキルチオ基、C1〜C6アルキルスルフィニル基、C1〜C6アルキルスルホニル基、アミノ基、モノ(C1〜C6アルキル)アミノ基、ジ(C1〜C6アルキル)アミノ基、シアノ基又はニトロ基を示し、
R6は、水素原子、C1〜C12アルキル基、C1〜C6アルコキシC1〜C6アルキル基、C1〜C12ハロアルキル基、C1〜C6アルコキシC1〜C6ハロアルキル基、C1〜C6ハロアルコキシC1〜C6アルキル基、C1〜C6ハロアルコキシC1〜C6ハロアルキル基、C2〜C7アルキニル基、C3〜C6シクロアルキルC2〜C6アルキニル基、C2〜C6ハロアルキニル基、C2〜C6アルケニル基、C2〜C6ハロアルケニル基、C3〜C6シクロアルキル基、C3〜C6ハロシクロアルキル基、C1〜C6ハロアルキルC3〜C6シクロアルキル基、C3〜C6シクロアルキルC1〜C6アルキル基、C3〜C6ハロシクロアルキルC1〜C6アルキル基、C1〜C6アルキルチオC1〜C6アルキル基、C1〜C6アルキルスルフィニルC1〜C6アルキル基、C1〜C6アルキルスルホニルC1〜C6アルキル基、C1〜C6ハロアルキルチオC1〜C6アルキル基、C1〜C6ハロアルキルスルフィニルC1〜C6アルキル基、C1〜C6ハロアルキルスルホニルC1〜C6アルキル基、C1〜C6アルキルカルボニルC1〜C6アルキル基、C1〜C6ハロアルキルカルボニルC1〜C6アルキル基、C1〜C6アルコキシカルボニルC1〜C6アルキル基、アミノカルボニルC1〜C6アルキル基、モノ(C1〜C6アルキル)アミノカルボニルC1〜C6アルキル基、モノ(C3〜C6シクロアルキル)アミノカルボニルC1〜C6アルキル基、モノ(C1〜C6ハロアルキル)アミノカルボニルC1〜C6アルキル基、ジ(C1〜C6アルキル)アミノカルボニルC1〜C6アルキル基、モノ(C1〜C6アルキルカルボニル)アミノC1〜C6アルキル基、モノ(C1〜C6アルコキシカルボニル)アミノC1〜C6アルキル基、モノ(C1〜C6アルキル)スルホニルアミノC1〜C6アルキル基、モノ(C1〜C6ハロアルキルスルホニル)アミノC1〜C6アルキル基、ヒドロキシC1〜C6アルキル基、ヒドロキシイミノC1〜C6アルキル基、C1〜C6アルコキシイミノC1〜C6アルキル基、C1〜C6ハロアルコキシイミノC1〜C6アルキル基又は無置換の若しくはR9で置換されたC7〜C13アラルキル基を示し、
R7及びR8は、各々独立して水素原子、C1〜C6アルキル基、C3〜C6シクロアルキル基、C3〜C6シクロアルキルC1〜C6アルキル基、C2〜C7アルキニル基、C2〜C6アルケニル基、ヒドロキシ基、C1〜C6アルコキシ基、C1〜C6アルコキシC1〜C6アルキル基、C1〜C6ハロアルキル基、2−テトラヒドロフラニル基、3−テトラヒドロフラニル基、2−テトラヒドロピラニル基、4−テトラヒドロピラニル基、シアノC1〜C6アルキル基、シアノC3〜C6シクロアルキル基、ヒドロキシC1〜C6アルキル基、ホルミル基、アミノ基、モノ(C1〜C6アルキル)アミノ基、ジ(C1〜C6アルキル)アミノ基、C1〜C6アルキルカルボニル基、C1〜C6アルコキシC1〜C6アルキルカルボニル基、C3〜C6シクロアルキルカルボニル基、C3〜C6シクロアルキルC1〜C6アルキルカルボニル基、C1〜C6アルコキシカルボニル基、カルバモイル基、モノ(C1〜C6アルキル)アミノカルボニル基、ジ(C1〜C6アルキル)アミノカルボニル基、無置換の若しくはR9で置換されたフェニルカルボニル基、無置換の若しくはR9で置換されたC7〜C13アラルキルカルボニル基、無置換の若しくはR9で置換されたピリジルカルボニル基、無置換の若しくはR9で置換されたピラゾリルカルボニル基、(C1〜C6アルキル)チオカルボニル基、(C1〜C6アルコキシ)チオカルボニル基、チオカルバモイル基、モノ(C1〜C6アルキル)アミノチオカルボニル基、ジ(C1〜C6アルキル)アミノチオカルボニル基、C1〜C6アルキルスルホニル基、スルファモイル基、モノ(C1〜C6アルキル)アミノスルホニル基、ジ(C1〜C6アルキル)アミノスルホニル基、R10R11N−C1〜C6アルキル基、C1〜C6アルコキシカルボニルC1〜C6アルキル基、アミノカルボニルC1〜C6アルキル基、モノ(C1〜C6アルキル)アミノカルボニルC1〜C6アルキル基、モノ(C3〜C6シクロアルキル)アミノカルボニルC1〜C6アルキル基、モノ(C1〜C6ハロアルキル)アミノカルボニルC1〜C6アルキル基、ジ(C1〜C6アルキル)アミノカルボニルC1〜C6アルキル基、ヒドロキシイミノ基、C1〜C6アルコキシイミノ基、ヒドロキシイミノC1〜C6アルキル基、C1〜C6アルコキシイミノC1〜C6アルキル基、を示し、また、R7とR8は一緒になって=CR12N(R13)R14または=CR12OR15を形成してもよく、さらに、R7とR8はこれらの結合する炭素原子と共に3〜6員の炭素環、又は酸素原子、硫黄原子及び窒素原子により選択される1〜4個のヘテロ原子を有する3〜6員の複素環を形成してもよく、該複素環はハロゲン原子、シアノ基、ニトロ基、C1〜C6アルキル基、C1〜C6アルコキシ基、C1〜C6ハロアルキル基又はオキソ基によって置換されてもよく、
R9は、ハロゲン原子、C1〜C6アルキル基、C1〜C6ハロアルキル基、C1〜C6アルコキシ基、C1〜C6ハロアルコキシ基、C1〜C6アルキルチオ基、C1〜C6アルキルスルフィニル基、C1〜C6アルキルスルホニル基、C1〜C6ハロアルキルチオ基、C1〜C6ハロアルキルスルフィニル基、C1〜C6ハロアルキルスルホニル基、アミノ基、モノ(C1〜C6アルキル)アミノ基、ジ(C1〜C6アルキル)アミノ基、シアノ基又はニトロ基を示し、
R10及びR11は、各々独立して水素原子、C1〜C6アルキル基、C1〜C6ハロアルキル基又はC3〜C6シクロアルキル基を示し、さらに、R10とR11はこれらの結合する炭素原子と共に3〜6員環を形成してもよく、
R12は、水素原子、C1〜C6アルキル基、C3〜C6シクロアルキル基を示し、
R13及びR14は、各々独立して水素原子、C1〜C6アルキル基、、C1〜C6ハロアルキル基、C3〜C6シクロアルキル基、C1〜C6アルコキシ基を示し、さらに、R13とR14はこれらの結合する炭素原子と共に3〜6員の炭素環、又は酸素原子、硫黄原子及び窒素原子により選択される1〜4個のヘテロ原子を有する3〜6員の複素環を形成してもよく、
R15は、C1〜C6アルキル基を示す。]
で表されるピラゾール−3−カルボン酸アミド誘導体、又はその農業上許容される塩。
nは、0又は1の整数を示し、
R1、R2、R3、R4及びR5は、各々独立して水素原子、ハロゲン原子、C1〜C6アルキル基、C1〜C6ハロアルキル基、C1〜C6アルコキシ基、C1〜C6ハロアルコキシ基、C3〜C6シクロアルキル基、C1〜C6アルキルチオ基、C1〜C6アルキルスルフィニル基、C1〜C6アルキルスルホニル基、アミノ基、モノ(C1〜C6アルキル)アミノ基、ジ(C1〜C6アルキル)アミノ基、シアノ基又はニトロ基を示し、
R6は、水素原子、C1〜C12アルキル基、C1〜C6アルコキシC1〜C6アルキル基、C1〜C12ハロアルキル基、C1〜C6アルコキシC1〜C6ハロアルキル基、C1〜C6ハロアルコキシC1〜C6アルキル基、C1〜C6ハロアルコキシC1〜C6ハロアルキル基、C2〜C7アルキニル基、C3〜C6シクロアルキルC2〜C6アルキニル基、C2〜C6ハロアルキニル基、C2〜C6アルケニル基、C2〜C6ハロアルケニル基、C3〜C6シクロアルキル基、C3〜C6ハロシクロアルキル基、C1〜C6ハロアルキルC3〜C6シクロアルキル基、C3〜C6シクロアルキルC1〜C6アルキル基、C3〜C6ハロシクロアルキルC1〜C6アルキル基、C1〜C6アルキルチオC1〜C6アルキル基、C1〜C6アルキルスルフィニルC1〜C6アルキル基、C1〜C6アルキルスルホニルC1〜C6アルキル基、C1〜C6ハロアルキルチオC1〜C6アルキル基、C1〜C6ハロアルキルスルフィニルC1〜C6アルキル基、C1〜C6ハロアルキルスルホニルC1〜C6アルキル基、C1〜C6アルキルカルボニルC1〜C6アルキル基、C1〜C6ハロアルキルカルボニルC1〜C6アルキル基、C1〜C6アルコキシカルボニルC1〜C6アルキル基、アミノカルボニルC1〜C6アルキル基、モノ(C1〜C6アルキル)アミノカルボニルC1〜C6アルキル基、モノ(C3〜C6シクロアルキル)アミノカルボニルC1〜C6アルキル基、モノ(C1〜C6ハロアルキル)アミノカルボニルC1〜C6アルキル基、ジ(C1〜C6アルキル)アミノカルボニルC1〜C6アルキル基、モノ(C1〜C6アルキル)カルボニルアミノC1〜C6アルキル基、モノ(C1〜C6アルコキシ)カルボニルアミノC1〜C6アルキル基、モノ(C1〜C6アルキルスルホニル)アミノC1〜C6アルキル基、モノ(C1〜C6ハロアルキルスルホニル)アミノC1〜C6アルキル基、ヒドロキシC1〜C6アルキル基、ヒドロキシイミノC1〜C6アルキル基、C1〜C6アルコキシイミノC1〜C6アルキル基、C1〜C6ハロアルコキシイミノC1〜C6アルキル基、無置換の又はR9で置換されたC7〜C13アラルキル基、を示し、
R16は水素原子又はC1〜C6アルキル基を示す。]
で表されるピラゾール−3−カルボン酸誘導体、又はその塩。
(4−CF3)Ph:4−トリフルオロメチルフェニル
(2−F−4−CF3)Ph:2−フルオロ−4−トリフルオロメチルフェニル
本発明化合物のうち、一般式[V]で表される化合物は、例えば以下の方法に従い製造することができる。
即ち、一般式[V]で表される化合物は、一般式[III]で表される化合物と一般式[IV]で表される化合物とを、適当な溶媒中、適当な塩基の存在下又は非存在下、反応させることにより製造することができる。
本発明化合物のうち、一般式[VI]で表される化合物は、例えば以下の方法に従い製造することができる。
即ち、一般式[VI]で表される化合物は、適当な溶媒中、化合物[III]を適当な塩基又は適当な酸の存在下、加水分解反応を行うことにより製造することができる。
本発明化合物のうち、一般式[V]で表される化合物は、例えば以下の方法に従い製造することもできる。
即ち、一般式[V]で表される化合物は、(工程1)適当な溶媒中、適当な触媒の存在下又は非存在下、化合物[VI]を酸ハロゲン化剤を用いて化合物[VII]とした後、(工程2)適当な溶媒中、適当な塩基の存在下又は非存在下、化合物[IV]と反応させることにより製造することができる。
本反応で使用できる酸ハロゲン化剤としては、塩化チオニル、オキサリルクロリド又は塩化ホスホリル等を挙げることができる。尚、酸ハロゲン化剤の使用量は、化合物[VI]1モルに対して0.1〜30モルの範囲から適宜選択すればよく、好ましくは0.5〜6モルである。
本反応で使用する化合物[IV]の使用量は、化合物[VI]1モルに対して通常1〜500モルの範囲から適宜選択すればよく、好ましくは1.0〜300モルである。
本発明化合物のうち、一般式[V]で表される化合物は、例えば以下の方法に従い製造することもできる。
即ち、一般式[V]で表される化合物は、化合物[VI]と化合物[IV]とを、適当な縮合剤及び適当な塩基の存在下又は非存在下、適当な溶媒中において反応させることにより製造することができる。
本発明化合物のうち、一般式[IX]で表される化合物は、例えば一般式[VIII]で表される化合物を用いて以下の方法に従い製造することができる。
即ち、一般式[IX]で表される化合物は、水素ガス雰囲気下、化合物[VIII]を適当な触媒の存在下、適当な溶媒中において加水素分解反応させることにより製造することができる。
本発明化合物のうち、一般式[XII]で表される化合物は、例えば一般式[IX]で表される化合物を用いて以下の方法に従い製造することができる。
即ち、一般式[XII]で表される化合物は、化合物[IX]と化合物[X]又は化合物[XI]とを、適当な溶媒中、適当な塩基の存在下又は非存在下で反応させることにより製造することができる。
本発明化合物のうち、一般式[XII]で表される化合物は、例えば一般式[IX]で表される化合物を用いて以下の方法に従い製造することができる。
即ち、一般式[XII]で表される化合物は、化合物[IX]と化合物[XIII]とを、適当な溶媒中、トリ置換ホスフィン及びアゾジカルボン酸誘導体の存在下、若しくはホスホラン試薬の存在下で反応させることにより製造することができる。
本発明化合物のうち、一般式[V]で表される化合物は、例えば一般式[XIV]で表される化合物を用いて以下の方法に従い製造することができる。
即ち、一般式[V]で表される化合物は、化合物[XIV]と化合物[XV]又は化合物[XVI]とを、適当な溶媒中、適当な塩基の存在下又は非存在下で反応させることにより製造することができる。
本発明化合物のうち、一般式[XVII]で表される化合物は、例えば一般式[V]で表される化合物を用いて以下の方法に従い製造することができる。
即ち、一般式[XVII]で表される化合物は、化合物[V]と適当な硫化剤とを反応させることにより製造することができる。
本発明化合物のうち、一般式[XIX]で表される化合物は、例えば一般式[XVIII]で表される化合物を用いて以下の方法に従い製造することができる。
一般式[XXIII]で表される化合物は、例えば一般式[XX]で表される化合物を用いて以下の方法に従い製造することができる。
即ち、一般式[XXIII]で表される化合物は、化合物[XX]と化合物[XXI]とのヤップ・クリンゲマン(Japp−klingemann)反応により化合物[XXII]を得た後、環化反応させることにより得ることができる。又、一般式[XXIII]で表される化合物は、国際公開第2012/028332号、国際公開第2014/114649号、国際公開第2016/027790号、国際公開第2016/166250号又は米国特許第5,055,482号明細書に記載された方法又はその方法に準じて製造することができる。
殺虫活性成分:アクリナトリン(acrinathrin)、アザジラクチン(azadirachtin)、アザメチホス(azamethiphos)、アシノナピル(acynonapyr)、アジンホス・エチル(azinphos−ethyl)、アジンホス・メチル(azinphos−methyl)、アセキノシル(acequinocyl)、アセタミプリド(acetamiprid)、アセトプロール(acetoprole)、アセフェート(acephate)、アゾシクロチン(azocyclotin)、アバメクチン(abamectin)、アフィドピロペン(afidopyropen)、アフォキソレイナー(afoxolaner)、アミドフルメット(amidoflumet)、アミトラズ(amitraz)、アラニカルブ(alanycarb)、アルジカルブ(aldicarb)、アルドキシカルブ(aldoxycarb)、アレスリン(allethrin)[d−cis−trans−体、d−trans−体を含む]、イサゾホス(isazophos)、イサミドホス(isamidofos)、イソカルボホス(isocarbophos)、イソキサチオン(isoxathion)、イソフェンホス・メチル(isofenphos−methyl)、イソプロカルブ(isoprocarb)、イプシロン−メトフルトリン(epsilon−metofluthrin)、イプシロン−モムフルオロスリン(epsilon−momfluorothrin)、イベルメクチン(ivermectin)、イミシアホス(imicyafos)、イミダクロプリド(imidacloprid)、イミプロトリン(imiprothrin)、インドキサカルブ(indoxacarb)、エスフェンバレレート(esfenvalerate)、エチオフェンカルブ(ethiofencarb)、エチオン(ethion)、エチプロール(ethiprole)、エチレンジブロミド(ethylene dibromide)、エトキサゾール(etoxazole)、エトフェンプロックス(etofenprox)、エトプロホス(ethoprophos)、エトリムホス(etrimfos)、エマメクチン(emamectin)、エマメクチンベンゾエート(emamectin benzoate)、エンドスルファン(endosulfan)、エンペントリン(empenthrin)、オキサゾスルフィル(oxazosulfyl)、オキサミル(oxamyl)、オキシジメトン・メチル(oxydemeton−methyl)、オキシデプロホス(oxydeprofos)、オメトエート(omethoate)、カズサホス(cadusafos)、カッパ−テフルトリン(kappa−tefluthrin)、カッパ−ビフェントリン(kappa−bifenthrin)、カランジン(karanjin)、カルタップ(cartap)、カルバリル(carbaryl)、カルボスルファン(carbosulfan)、カルボフラン(carbofuran)、ガンマ−BHC(gamma−BHC)、キシリルカルブ(xylylcarb)、キナルホス(quinalphos)、キノプレン(kinoprene)、キノメチオネート(chinomethionat)、クマホス(coumaphos)、クリオライト(cryolite)、クロチアニジン(clothianidin)、クロフェンテジン(clofentezine)、クロマフェノジド(chromafenozide)、クロラントラニリプロール(chlorantraniliprole)、クロルエトキシホス(chlorethoxyfos)、クロルデン(chlordane)、クロルピクリン(chloropicrin)、クロルピリホス(chlorpyrifos)、クロルピリホス・メチル(chlorpyrifos−methyl)、クロルフェナピル(chlorfenapyr)、クロルフェンビンホス(chlorfenvinphos)、クロルフルアズロン(chlorfluazuron)、クロルメホス(chlormephos)、クロロプラレスリン(chloroprallethrin)、シアジピル(cyazypyr)、シアノホス(cyanophos)、ジアフェンチウロン(diafenthiuron)、ジアミダホス(diamidafos)、シアントラニリプロール(cyantraniliprole)、ジエノクロル(dienochlor)、シエノピラフェン(cyenopyrafen)、ジオキサベンゾホス(dioxabenzofos)、ジオフェノラン(diofenolan)、シクラニリプロール(cyclaniliprole)、シクロキサプリド(cycloxaprid)、ジクロトホス(dicrotophos)、ジクロフェンチオン(dichlofenthion)、シクロプロトリン(cycloprothrin)、ジクロルボス(dichlorvos)、ジクロロメゾチアズ(dicloromezotiaz)、ジコホル(dicofol)、ジシクラニル(dicyclanil)、ジスルホトン(disulfoton)、ジノテフラン(dinotefuran)、ジノブトン(dinobuton)、シハロジアミド(cyhalodiamide)、シハロトリン(cyhalothrin)[gamma−体,lambda−体を含む]、シフェノトリン(cyphenothrin)[(1R)−trans−体を含む]、シフルトリン(cyfluthrin)[beta−体を含む]、ジフルベンズロン(diflubenzuron)、シフルメトフェン(cyflumetofen)、ジフロビダジン(diflovidazin)、シヘキサチン(cyhexatin)、シペルメトリン(cypermethrin)[alpha−体,beta−体,theta−体,zeta−体を含む]、ジメチル−2,2,2−トリクロロ−1−ヒドロキシエチルホスホネート(DEP)、ジメチルビンホス(dimethylvinphos)、ジメトエート(dimethoate)、ジメフルスリン(dimefluthrin)、シラフルオフェン(silafluofen)、シロマジン(cyromazine)、スピネトラム(spinetoram)、スピノサド(spinosad)、スピロジクロフェン(spirodiclofen)、スピロテトラマト(spirotetramat)、スピロピジオン(spiropidion)、スピロメシフェン(spiromesifen)、スルコフロン・ナトリウム塩(sulcofuron−sodium)、スルフルラミド(sulfluramid)、スルホキサフロル(sulfoxaflor)、スルホテップ(sulfotep)、ダイアジノン(diazinon)、チアクロプリド(thiacloprid)、チアメトキサム(thiamethoxam)、チオキサザフェン(tioxazafen)、チオジカルブ(thiodicarb)、チオシクラム(thiocyclam)、チオスルタップ(thiosultap)、チオナジン(thionazin)、チオファノックス(thiofanox)、チオメトン(thiometon)、チクロピラゾフロール(tyclopyrazoflor)、テトラクロラントラニリプロール(tetrachlorantraniliprole)、テトラクロルビンホス(tetrachlorvinphos)、テトラジホン(tetradifon)、テトラニリプロール(tetraniliprole)、テトラメチルフルスリン(tetramethylfluthrin)、テトラメトリン(tetramethrin)、テブピリムホス(tebupirimfos)、テブフェノジド(tebufenozide)、テブフェンピラド(tebufenpyrad)、テフルトリン(tefluthrin)、テフルベンズロン(teflubenzuron)、デメトン・S・メチル(demeton−S−methyl)、テメホス(temephos)、デルタメトリン(deltamethrin)、テルブホス(terbufos)、トラロメトリン(tralomethrin)、トランスフルトリン(transfluthrin)、トリアザメート(triazamate)、トリアゾホス(triazophos)、トリクロルホン(trichlorfon)、トリフルムロン(triflumuron)、トリフルメゾピリム(triflumezopyrim)、トリメタカルブ(trimethacarb)、トルフェンピラド(tolfenpyrad)、ナレッド(naled)、ニコチン(nicotine)、ニテンピラム(nitenpyram)、ネマデクチン(nemadectin)、ノバルロン(novaluron)、ノビフルムロン(noviflumuron)、バーティシリウム レカニ(Verticillium lecanii)、ハイドロプレン(hydroprene)、バシルス・スフェリカス(Bacillus sphaericus)、バシルス・ズブチリス(Bacillus subtillis)、バシルス・チューリンゲンシス(Bacillus thuringiensis)、バシルス・チューリンゲンシス(Bacillus thuringiensis)の生産する昆虫毒素、バシルス・チューリンゲンシス・亜種・アイザワイ(Bacillus thuringiensis subsp. Aizawai)、バシルス・チューリンゲンシス・亜種・イスラエレンシス(Bacillus thuringiensis subsp. Israelensis)、バシルス・チューリンゲンシス・亜種・クルスターキ(Bacillus thuringiensis subsp. Kurstaki)、バシルス・チューリンゲンシス・亜種・テネブリオニス(Bacillus thuringiensis subsp. Tenebrionis)、バシルス・ポピリエ(Bacillus popilliae)、パスツーリアペネトランス胞子(Pasteuriapenetrans)、バミドチオン(vamidothion)、パラチオン(parathion)、パラチオン・メチル(parathion−methyl)、ハルフェンプロックス(halfenprox)、ハロフェノジド(halofenozide)、ビオアレスリン(bioallethrin)、ビオアレスリンS‐シクロペンテニル(bioallethrin S−cyclopentenyl)、ビオレスメトリン(bioresmethrin)、ビス−(2−クロロ−1−メチルエチル)エーテル(DCIP)、ビストリフルロン(bistrifluron)、ヒドラメチルノン(hydramethylnon)、ビフェナゼート(bifenazate)、ビフェントリン(bifenthrin)、ピフルブミド(pyflubumide)、ピペロニルブトキシド(piperonyl butoxide)、ピメトロジン(pymetrozine)、ピラクロホス(pyraclofos)、ピラフルプロール(pyrafluprole)、ピリダフェンチオン(pyridaphenthion)、ピリダベン(pyridaben)、ピリダリル(pyridalyl)、ピリフルキナゾン(pyrifluquinazon)、ピリプロール(pyriprole)、ピリプロキシフェン(pyriproxyfen)、ピリミカルブ(pirimicarb)、ピリミジフェン(pyrimidifen)、ピリミノストロビン(pyriminostrobin)、ピリミホス・メチル(pirimiphos−methyl)、ピレトリン(pyrethrine)、ファムフル(famphur)、フィプロニル(fipronil)、フェナザキン(fenazaquin)、フェナミホス(fenamiphos)、フェニトロチオン(fenitrothion)、フェノキシカルブ(fenoxycarb)、フェノチオカルブ(fenothiocarb)、フェノト
リン(phenothrin)[(1R)−trans−体を含む]、フェノブカルブ(fenobucarb)、フェンチオン(fenthion)、フェントエート(phenthoate)、フェンバレレート(fenvalerate)、フェンピロキシメート(fenpyroximate)、フェンブタンチン・オキシド(fenbutatin oxide)、フェンプロパトリン(fenpropathrin)、フォノホス(fonofos)、フッ化スルフリル(sulfuryl fluoride)、ブトカルボキシム(butocarboxim)、ブトキシカルボキシム(butoxycarboxim)、ブプロフェジン(buprofezin)、フラチオカルブ(furathiocarb)、プラレトリン(prallethrin)、フルアクリピリム(fluacrypyrim)、フルアザインドリジン(fluazaindolizine)、フルアズロン(fluazuron)、フルエンスルホン(fluensulfone)、フルオピラム(fluopyram)、フルオロ酢酸ナトリウム塩(sodium fluoroacetate)、フルキサメタミド(fluxametamide)、フルシクロクスロン(flucycloxuron)、フルシトリネート(flucythrinate)、フルスルファミド(flusulfamide)、フルトリン(fluthrin)、フルバリネート(fluvalinate) [tau−体を含む]、フルピラジフロン(flupyradifurone)、フルピラゾホス(flupyrazofos)、フルピリミン(flupyrimin)、フルフィプロール(flufiprole)、フルフェネリム(flufenerim)、フルフェノキシストロビン(flufenoxystrobin)、フルフェノクスロン(flufenoxuron)、フルヘキサフォン(fluhexafon)、フルベンジアミド(flubendiamide)、フルメトリン(flumethrin)、フルララナル(fluralaner)、フルリムフェン(flurimfen)、プロチオホス(prothiofos)、プロトリフェンブト(protrifenbute)、フロニカミド(flonicamid)、プロパホス(propaphos)、プロパルギット(propargite)、プロフェノホス(profenofos)、ブロフラニリド(broflanilide)、プロフルトリン(profluthrin)、プロペタムホス(propetamphos)、プロポキスル(propoxur)、フロメトキン(flometoquin)、ブロモプロピレート(bromopropylate)、ヘキサチアゾクス(hexythiazox)、ヘキサフルムロン(hexaflumuron)、ペキロマイセス・テヌイペス(Pacilimyces tenuipes)、ペキロマイセス・フモソロセウス(Paecilomyces fumosoroceus)、ヘプタフルスリン(heptafluthrin)、ヘプテノホス(heptenophos)、ペルメトリン(permethrin)、ベンクロチアズ(benclothiaz)、ベンズピリモキサン(benzpyrimoxan)、ベンスルタップ(bensultap)、ベンゾキシメート(benzoximate)、ベンダイオカルブ(bendiocarb)、ベンフラカルブ(benfuracarb)、ボーベリア・テネーラ(Beauveria tenella)、ボーベリア・バッシアーナ(Beauveria bassiana)、ボーベリア・ブロンニアティ(Beauveria brongniartii)、ホキシム(phoxim)、ホサロン(phosalone)、ホスチアゼート(fosthiazate)、ホスチエタン(fosthietan)、ホスファミドン(phosphamidon)、ホスメット(phosmet)、ポリナクチン複合体(polynactins)、ホルメタネート(formetanate)、ホレート(phorate)、マラチオン(malathion)、ミルベメクチン(milbemectin)、メカルバム(mecarbam)、メスルフェンホス(mesulfenfos)、メソミル(methomyl)、メタアルデヒド(metaldehyde)、メタフルミゾン(metaflumizone)、メタミドホス(methamidophos)、メタム(metham)、メチオカルブ(methiocarb)、メチダチオン(methidathion)、メチルイソチオシアネート(methyl isothiocyanate)、メチルブロマイド(methyl bromide)、メトキシクロル(methoxychlor)、メトキシフェノジド(methoxyfenozide)、メトトリン(methothrin)、メトフルトリン(metofluthrin)、メトプレン(methoprene)、メトルカルブ(metolcarb)、メビンホス(mevinphos)、メペルフルスリン(meperfluthrin)、モナクロスポリウム・フィマトパガム(Monacrosporium phymatophagum)、モノクロトホス(monocrotophos)、モムフルオロスリン(momfluorothrin)、リトルアA(litlure−A)、リトルアB(litlure−B)、りん化アルミニウム(aluminium phosphide)、りん化亜鉛(zinc phosphide)、りん化水素(phosphine)、ルフェヌロン(lufenuron)、レスカルレ(rescalure)、レスメトリン(resmethrin)、レピメクチン(lepimectin)、ロテノン(rotenone)、核多角体病ウイルス包埋体、酸化フェンブタスズ(fenbutatin oxide)、石灰窒素(calcium cyanide)、有機スズ化合物(organotins)、硫酸ニコチン(nicotine−sulfate)、(Z)−11−テトラデセニル=アセタート、(Z)−11−ヘキサデセナール、(Z)−11−ヘキサデセニル=アセタート、(Z)−9,12−テトラデカジエニル=アセタート、(Z)−9−テトラデセン−1−オール、(Z,E)−9,11−テトラデカジエニル=アセタート、(Z,E)−9,12−テトラデカジエニル=アセタート、1,1,1−トリクロロ−2,2−ビス(4−クロロフェニル)エタン(DDT)、1,3‐ジクロロプロペン(1,3−dichloropropene)、2,4−ジクロロ−5−{2−[4−(トリフルオロメチル)フェニル]エトキシ}フェニル 2,2,2−トリフルオロエチル スルホキシド(化学名、CAS登録番号:1472050−04−6)、2,4−ジクロロ−5−{2−[4−(トリフルオロメチル)フェニル]エトキシ}フェニル 2,2,2−トリフルオロエチル スルホキシド(化学名、CAS登録番号:1472052−11−1)、2,4−ジメチル−5−[6−(トリフルオロメチルチオ)へキシルオキシ]フェニル−2,2,2−トリフルオロエチル スルホキシド(化学名、CAS登録番号:1472050−34−2)、2−{2−フルオロ−4‐メチル−5−[(2,2,2−トリフルオロエチル)スルフィニル]フェノキシ}−5−(トリフルオロメチル)ピリジン(化学名、CAS登録番号:1448758−62−0)、3−クロロ−2−{2−フルオロ−4‐メチル−5−[(2,2,2−トリフルオロエチル)スルフィニル]フェノキシ}−5−(トリフルオロメチル)ピリジン(化学名、CAS登録番号:1448761−28−1)、4,6−ジニトロ−o−クレゾール(DNOC)、4−フルオロ−2−メチル−5−(5,5−ジメチルヘキシルオキシ]フェニル−2,2,2−トリフルオロエチル スルホキシド(化学名、CAS登録番号:1472047−71−4)、Btタンパク質 (Cry1Ab, Cry1Ac, Cry1Fa, Cry2Ab, mCry3A, Cry3Ab, Cry3Bb, Cry34/35Ab1)、CL900167(コード番号)、NA−85(コード番号)、NI−30(コード番号)、O,O−ジエチル−O−[4−(ジメチルスルファモイル)フェニル]−ホスホロチオネート(DSP)、O−エチル−O−4−(ニトロフェニル)フェニルホスホノチオエート (EPN)、RU15525(コード番号)、XMC(XMC)、Z−13−イコセン−10−オン、ZXI8901(コード番号)。
アザコナゾール(azaconazole)、アシベンゾラル・S・メチル(acibenzolar−S−methyl)、アゾキシストロビン(azoxystrobin)、アニラジン(anilazine)、アミスルブロム(amisulbrom)、アミノピリフェン(aminopyrifen)、アメトクトラジン(ametoctradin)、アルジモルフ(aldimorph)、イソチアニル(isotianil)、イソピラザム(isopyrazam)、イソフェタミド(isofetamid)、イソフルシプラム(isoflucypram)、イソプロチオラン(isoprothiolane)、イプコナゾール(ipconazole)、イプフルフェノキン(ipflufenoquin)、イプフェントリフルコナゾール(ipfentrifluconazole)、イプロジオン(iprodione)、イプロバリカルブ(iprovalicarb)、イプロベンホス(iprobenfos)、イマザリル(imazalil)、イミノクタジン・アルベシル酸塩(iminoctadine−albesilate)、イミノクタジン酢酸塩(iminoctadine− triacetate)、イミベンコナゾール(imibenconazole)、インピルフルキサム(inpyrfluxam)、インプリマチンA(imprimatin A)、インプリマチンB(imprimatin B)、エジフェンホス(edifenphos)、エタコナゾ−ル(etaconazole)、エタボキサム(ethaboxam)、エチリモル(ethirimol)、エトキシキン(ethoxyquin)、エトリジアゾール(etridiazole)、エネストロブリン(enestroburin)、エノキサストロビン(enoxastrobin)、エポキシコナゾール(epoxiconazole)、オーガニックオイル(organic oils)、オキサジキシル(oxadixyl)、オキサジニラゾール(oxazinylazole)、オキサチアピプロリン(oxathiapiprolin)、オキシカルボキシン(oxycarboxin)、オキシキノリン銅(oxine−copper)、オキシテトラサイクリン(oxytetracycline)、オキスポコナゾールフマル酸塩(oxpoconazole−fumarate)、オキソリニック酸(oxolinic acid)、オクタン酸銅(copper dioctanoate)、オクチリノン(octhilinone)、オフラセ(ofurace)、オリサストロビン(orysastrobin)、オルソフェニルフェノール(o−phenylphenol)、カスガマイシン(kasugamycin)、カプタホール(captafol)、カルプロパミド(carpropamid)、カルベンダジム(carbendazim)、カルボキシン(carboxin)、カルボネ(carvone)、キノキシフェン(quinoxyfen)、キノフメリン(quinofumelin)、キノメチオネート(chinomethionat)、キャプタン(captan)、キンコナゾール(quinconazole)、キントゼン(quintozene)、グアザチン(guazatine)、クフラネブ(cufraneb)、クメトキシストロビン(coumethoxystrobin)、クモキシストロビン(coumoxystrobin)、クレソキシム・メチル(kresoxim−methyl)、クロジラコン(clozylacon)、クロゾリネート(chlozolinate)、クロロタロニル(chlorothalonil)、クロロネブ(chloroneb)、シアゾファミド(cyazofamid)、ジエトフェンカルブ(diethofencarb)、ジクロシメット(diclocymet)、ジクロフルアニド(dichlofluanid)、ジクロベンチアゾクス(dichlobentiazox)、ジクロメジン(diclomezine)、ジクロラン(dicloran)、ジクロロフェン(dichlorophen)、ジチアノン(dithianon)、ジニコナゾール(diniconazole)、ジニコナゾール・M(diniconazole−M)、ジネブ(zineb)、ジノカップ(dinocap)、ジピメチトロン(dipymetitrone)、ジフェニルアミン(diphenylamine)、ジフェノコナゾール(difenoconazole)、シフルフェナミド(cyflufenamid)、ジフルメトリム(diflumetorim)、シプロコナゾール(cyproconazole)、シプロジニル(cyprodinil)、シメコナゾール(simeconazole)、ジメチリモル(dimethirimol)、ジメチルジスルフィド(dimethyl disulfide)、ジメトモルフ(dimethomorph)、シモキサニル(cymoxanil)、ジモキシストロビン(dimoxystrobin)、シュードモナス・ロデシア・HAI−0804(Pseudomonas rhodesiae HAI−0804)、ジラム(ziram)、シルチオファム(silthiofam)、ストレプトマイシン(streptomycin)、スピロキサミン(spiroxamine)、セダキサン(sedaxane)、ゾキサミド(zoxamide)、ソラテノール(solatenol)、ダゾメット(dazomet)、タラロマイセス フラバス(Talaromyces flavus)、チアジニル(tiadinil)、チアベンダゾール(thiabendazole)、チウラム(thiram)、チオファネート(thiophanate)、チオファネート・メチル(thiophanate−methyl)、チフルザミド(thifluzamide)、チラム(thiram)、テクナゼン(tecnazene)、テクロフタラム(tecloftalam)、テトラコナゾール(tetraconazole)、デバカルブ(debacarb)、テブコナゾール(tebuconazole)、テブフロキン(tebufloquin)、テルビナフィン(terbinafine)、ドジン(dodine)、ドデモルフ(dodemorph)、トリアジメノール(triadimenol)、トリアジメホン(triadimefon)、トリアゾキシド(triazoxide)、トリクラミド(trichlamide)、トリクロピリカルブ(triclopyricarb)、トリコデルマ・アトロビリデ(Trichoderma atroviride)、トリシクラゾール(tricyclazole)、トリチコナゾール(triticonazole)、トリデモルフ(tridemorph)、トリフルミゾール(triflumizole)、トリフロキシストロビン(trifloxystrobin)、トリホリン(triforine)、トリルフルアニド(tolylfluanid)、トルクロホス・メチル(tolclofos−methyl)、トルニファニド(tolnifanide)、トルプロカルブ(tolprocarb)、ナーバム(nabam)、ナタマイシン(natamycin)、ナフティフィン(naftifine)、ニトラピリン(nitrapyrin)、ニトロタル・イソプロピル(nitrothal−isopropyl)、ヌアリモル(nuarimol)、ノニルフェノールスルホン酸銅(copper nonyl phenol sulphonate)、バチルス・ズブチリス(Bacillus subtilis)(strain:QST 713)、バリダマイシン(validamycin)、バリフェナレート(valifenalate)、ピカルブトラゾックス(picarbutrazox)、ビキサフェン(bixafen)、ピコキシストロビン(picoxystrobin)、ピジフルメトフェン(pydiflumetofen)、ビテルタノール(bitertanol)、ビナパクリル(binapacryl)、ヒノキチオール(hinokitiol)、ビフェニル(biphenyl)、ピペラリン(piperalin)、ヒメキサゾール(hymexazol)、ピラオキシストロビン(pyraoxystrobin)、ピラクロストロビン(pyraclostrobin)、ピラジフルミド(pyraziflumid)、ピラゾホス(pyrazophos)、ピラプロポイン(pyrapropoyne)、ピラメトストロビン(pyrametostrobin)、ピリオフェノン(pyriofenone)、ピリソキサゾール(pyrisoxazole)、ピリダクロメチル(pyridachlometyl)、ピリフェノックス(pyrifenox)、ピリブチカルブ(pyributicarb)、ピリベンカルブ(pyribencarb)、ピリメタニル(pyrimethanil)、ピロキロン(pyroquilon)、ビンクロゾリン(vinclozolin)、ファーバム(ferbam)、ファモキサドン(famoxadone)、フェナジンオキシド(phenazine oxide)、フェナミドン(fenamidone)、フェナミンストロビン(fenaminstrobin)、フェナリモル(fenarimol)、フェノキサニル(fenoxanil)、フェリムゾン(ferimzone)、フェンピクロニル(fenpiclonil)、フェンピコキサミド(fenpicoxamid)、フェンピラザミン(fenpyrazamine)、フェンブコナゾール(fenbuconazole)、フェンフラム(fenfuram)、フェンプロピジン(fenpropidin)、フェンプロピモルフ(fenpropimorph)、フェンヘキサミド(fenhexamid)、フォルペット(folpet)、フサライド(phthalide)、ブピリメート(bupirimate)、フベリダゾール(fuberidazole)、ブラストサイジン−S(blasticidin−S)、フラメトピル(furametpyr)、フララキシル(furalaxyl)、フランカルボン酸(furancarboxylic acid)、フルアジナム(fluazinam)、フルインダピル(fluindapyr)、フルオキサストロビン(fluoxastrobin)、フルオピコリド(fluopicolide)、フルオピモミド(fluopimomide)、フルオピラム(fluopyram)、フルオルイミド(fluoroimide)、フルキサピロキサド(fluxapyroxad)、フルキンコナゾール(fluquinconazole)、フルコナゾール(furconazole)、フルコナゾール・シス(furconazole −cis)、フルジオキソニル(fludioxonil)、フルシラゾール(flusilazole)、フルスルファミド(flusulfamide)、フルチアニル(flutianil)、フルトラニル(flutolanil)、フルトリアホール(flutriafol)、フルフェノキシストロビン(flufenoxystrobin)、フルメトベル(flumetover)、フルモルフ(flumorph)、プロキナジド(proquinazid)、プロクロラズ(prochloraz)、プロシミドン(procymidone)、プロチオカルブ(prothiocarb)、プロチオコナゾール(prothioconazole)、ブロノポール(bronopol)、プロパモカルブ塩酸塩(propamocarb−hydrochloride)、プロピコナゾール(propiconazole)、プロピネブ(propineb)、プロベナゾール(probenazole)、ブロムコナゾール(bromuconazole)、フロメトキン(flometoquin)、フロリルピコキサミド(florylpicoxamid)、ヘキサコナゾール(hexaconazole)、ベナ
ラキシル(benalaxyl)、ベナラキシル・M(benalaxyl−M)、ベノダニル(benodanil)、ベノミル(benomyl)、ペフラゾエート(pefurazoate)、ペンコナゾール(penconazole)、ペンシクロン(pencycuron)、ベンゾビンジフルピル(benzovindiflupyr)、ベンチアゾール(benthiazole)、ベンチアバリカルブ・イソプロピル(benthiavalicarb−isopropyl)、ペンチオピラド(penthiopyrad)、ペンフルフェン(penflufen)、ボスカリド(boscalid)、ホセチル(fosetyl)(alminium, calcium, sodium)、ポリオキシン(polyoxin)、ポリカーバメート(polycarbamate)、ボルドー液(Bordeaux mixture)、マンカッパー(mancopper)、マンコゼブ(mancozeb)、マンジプロパミド(mandipropamid)、マンデストロビン(mandestrobin)、マンネブ(maneb)、ミクロブタニル(myclobutanil)、ミネラルオイル(mineral oils)、ミルディオマイシン(mildiomycin)、メタスルホカルブ(methasulfocarb)、メタム(metam)、メタラキシル(metalaxyl)、メタラキシル・M(metalaxyl−M)、メチラム(metiram)、メチルテトラプロール(metyltetraprole)、メトコナゾール(metconazole)、メトミノストロビン(metominostrobin)、メトラフェノン(metrafenone)、メパニピリム(mepanipyrim)、メフェントリフルコナゾール(mefentrifluconazole)、メプチルジノカップ(meptyldinocap)、メプロニル(mepronil)、ヨードカルブ(iodocarb)、ラミナリン(laminarin)、リゾビウム・ビティス(Rhizobium vitis)、亜リン酸及び塩(phosphorous acid and salts)、塩基性塩化銅(copper oxychloride)、銀(silver)、酸化第一銅(cuprous oxide)、水酸化第二銅(copper hydroxide)、炭酸水素カリウム(potassium bicarbonate)、炭酸水素ナトリウム(sodium bicarbonate)、硫黄(sulfur)、硫酸オキシキノリン(oxyquinoline sulfate)、硫酸銅(copper sulfate)、(3,4−ジクロロイソチアゾール−5−イル)メチル 4−(tert−ブチル)安息香酸エステル(化学名、CAS登録番号:1231214−23−5)、BAF−045(コード番号)、BAG−010(コード番号)、UK−2A(コード番号)、ドデシルベンゼンスルホン酸ビスエチレンジアミン銅錯塩[II](DBEDC)、MIF−1002(コード番号)、NF−180(コード番号)、酢酸トリフェニルスズ(TPTA)、トリフェニルチンクロライド(TPTC)、水酸化トリフェニルスズ(TPTH)、非病原性エルビニア・カロトボーラ。
アイオキシニル(ioxynil)、アクロニフェン(aclonifen)、アクロレイン(acrolein)、アザフェニジン(azafenidin)、アシフルオルフェン(acifluorfen)(ナトリウムなどとの塩を含む)、アジムスルフロン(azimsulfuron)、アシュラム(asulam)、アセトクロ−ル(acetochlor)、アトラジン(atrazine)、アニロホス(anilofos)、アミカルバゾン(amicarbazone)、アミドスルフロン(amidosulfuron)、アミトロール(amitrole)、アミノシクロピラクロル(aminocyclopyrachlor)、アミノピラリド(aminopyralid)、アミプロホス・メチル(amiprofos−methyl)、アメトリン(ametryn)、アラクロール(alachlor)、アロキシジム(alloxydim)、アンシミドール(ancymidol)、イソウロン(isouron)、イソキサクロルトール(isoxachlortole)、イソキサフルトール(isoxaflutole)、イソキサベン(isoxaben)、イソデシルアルコールエトキシレート(Isodecylalkoholethoxylat)、イソプロツロン(isoproturon)、イプフェンカルバゾン(ipfencarbazone)、イマザキン(imazaquin)、イマザピク(imazapic)(アミン等との塩を含む)、イマザピル(imazapyr)(イソプロピルアミン等の塩を含む)、イマザメタベンズ(imazamethabenz−methyl)、イマザモックス(imazamox)、イマゼタピル(imazethapyr)、イマゾスルフロン(imazosulfuron)、インダジフラム(indaziflam)、インダノファン(indanofan)、エグリナジン・エチル(eglinazine−ethyl)、エスプロカルブ(esprocarb)、エタメトスルフロン・メチル(ethametsulfuron−methyl)、エタルフルラリン(ethalfluralin)、エチジムロン(ethidimuron)、エトキシスルフロン(ethoxysulfuron)、エトキシフェン(ethoxyfen−ethyl)、エトフメセート(ethofumesate)、エトベンザニド(etobenzanid)、エンドタール二ナトリウム塩(endothal−disodium)、オキサジアゾン(oxadiazon)、オキサジアルギル(oxadiargyl)、オキサジクロメホン(oxaziclomefone)、オキサスルフロン(oxasulfuron)、オキシフルオルフェン(oxyfluorfen)、オリザリン(oryzalin)、オルトスルファムロン(orthosulfamuron)、オルベンカルブ(orbencarb)、オレイン酸(oleic acid)、カフェンストロール(cafenstrole)、カルフェントラゾン・エチル(carfentrazone−ethyl)、カルブチレート(karbutilate)、カルベタミド(carbetamide)、キザロホップ(quizalofop)、キザロホップ・エチル(quizalofop−ethyl)、キザロホップ・P・エチル(quizalofop−P−ethyl)、キザロホップ・P・テフリル(quizalofop−P−tefuryl)、キノクラミン(quinoclamine)、キンクロラック(quinclorac)、キンメラック(quinmerac)、クミルロン(cumyluron)、クラシホス(clacyfos)、グリホサート(glyphosate)(ナトリウム、カリウム、アミン、プロピルアミン、イソプロピルアミン、ジメチルアミン又はトリメシウム等の塩を含む)、グルホシネート(glufosinate)(アミン又はナトリウム等の塩を含む)、グルホシネート・P(glufosinate−P)、グルホシネート・P・ナトリウム塩(glufosinate−P−sodium)、クレトジム(clethodim)、クロジナホップ・プロパルギル(clodinafop−propargyl)、クロピラリド(clopyralid)、クロマゾン(clomazone)、クロメトキシフェン(chlomethoxyfen)、クロメプロップ(clomeprop)、クロランスラム・メチル(cloransulam−methyi)、クロランベン(chloramben)、クロリダゾン(chloridazon)、クロリムロン・エチル(chlorimuron−ethyl)、クロルスルフロン(chlorsulfuron)、クロルタル・ジメチル(chlorthal−dimethyl)、クロルチアミド(chlorthiamid)、クロルフタリム(chlorphthalim)、クロルフルレノール・メチル(chlorflurenol−methyl)、クロルプロファム(chlorpropham)、クロルブロムロン(chlorbromuron)、クロロクスロン(chloroxuron)、クロロトルロン(chlorotoluron)、ケトスピラドックス(ketospiradox)(ナトリウム、カルシウム又はアンモニアなどの塩を含む)、サフルフェナシル(saflufenacil)、サルメンチン(sarmentine)、シアナジン(cyanazine)、シアナミド(cyanamide)、ジウロン(diuron)、ジエタチル・エチル(diethatyl−ethyl)、ジカンバ(dicamba)(アミン、ジエチルアミン、イソプロピルアミン、ジグリコールアミン、ナトリウム又はリチウム等の塩を含む)、シクロエート(cycloate)、シクロキシジム(cycloxydim)、ジクロスラム(diclosulam)、シクロスルファムロン(cyclosulfamuron)、シクロピラニル(cyclopyranil)、シクロピリモレート(cyclopyrimorate)、ジクロベニル(dichlobenil)、ジクロホップ・P・メチル(diclofop−P−methyl)、ジクロホップ・メチル(diclofop−methyl)、ジクロルプロップ(dichlorprop)、ジクロルプロップ−P(dichlorprop−P)、ジクワット(diquat)、ジチオピル(dithiopyr)、シデュロン(siduron)、ジニトラミン(dinitramine)、シニドン・エチル(cinidon−ethyl)、シノスルフロン(cinosulfuron)、ジノゼブ(dinoseb)、ジノテルブ(dinoterb)、シハロホップ・ブチル(cyhalofop−butyl)、ジフェナミド(diphenamid)、ジフェンゾコート(difenzoquat)、ジフルフェニカン(diflufenican)、ジフルフェンゾピル(diflufenzopyr)、シマジン(simazine)、ジメタクロール(dimethachlor)、ジメタメトリン(dimethametryn)、ジメテナミド(dimethenamid)、ジメテナミド・P(dimethenamid−P)、シメトリン(simetryn)、ジメピペレート(dimepiperate)、ジメフロン(dimefuron)、シンメチリン(cinmethylin)、スエップ(swep)、スルコトリオン(sulcotrione)、スルフェントラゾン(sulfentrazone)、スルホサート(sulfosate)、スルホスルフロン(sulfosulfuron)、スルホメツロンメチル(sulfometuron−methyl)、セトキシジム(sethoxydim)、ターバシル(terbacil)、ダイムロン(daimuron)、タキストミン・A(thaxtomin A)、ダラポン(dalapon)、チアゾピル(thiazopyr)、チアフェナシル(tiafenacil)、チエンカルバゾン(thiencarbazone)(ナトリウム塩、メチルエステル等を含む)、チオカルバジル(tiocarbazil)、チオベンカルブ(thiobencarb)、チジアジミン(thidiazimin)、チジアズロン(thidiazuron)、チフェンスルフロン・メチル(thifensulfuron−methyl)、デスメディファム(desmedipham)、デスメトリン(desmetryne)、テニルクロール(thenylchlor)、テブタム(tebutam)、テブチウロン(tebuthiuron)、テプラロキシジム(tepraloxydim)、テフリルトリオン(tefuryltrione)、テルブチラジン(terbuthylazine)、テルブトリン(terbutryn)、テルブメトン(terbumeton)、テンボトリオン(tembotrione)、トプラメゾン(topramezone)、トラルコキシジム(tralkoxydim)、トリアジフラム(triaziflam)、トリアスルフロン(triasulfuron)、トリアファモン(triafamone)、トリアレート(tri−allate)、トリエタジン(trietazine)、トリクロピル(triclopyr)、トリクロピル−ブトティル(triclopyr−butotyl)、トリトスルフロン(tritosulfuron)、トリフルジモキサジン(trifludimoxazin)、トリフルスルフロン・メチル(triflusulfuron−methyl)、トリフルラリン(trifluralin)、トリフロキシスルフロンナトリウム塩(trifloxysulfuron−sodium)、トリベニュロン・メチル(tribenuron−methyl)、トルピラレート(tolpyralate)、ナプタラム(naptalam)(ナトリウム等との塩を含む)、ナプロアニリド(naproanilide)、ナプロパミド(napropamide)、ナプロパミド−M(napropamide−M)、ニコスルフロン(nicosulfuron)、ネブロン(neburon)、ノルフルラゾン(norflurazon)、バーナレート(vernolate)、パラコート(paraquat dichloride)、ハルキシフェン・ベンジル(halauxifen−benzyl)、ハルキシフェン・メチル(halauxifen−methyl)、ハロキシホップ(haloxyfop)、ハロキシホップ・P(haloxyfop−P)、ハロキシホップ−エトティル(haloxyfop−etotyl)、ハロサフェン(halosafen)、ハロスルフロン・メチル(halosulfuron−methyl)、ピクロラム(picloram)、ピコリナフェン(picolinafen)、ビシクロピロン(bicyclopyrone)、ビスピリバック・ナトリウム塩(bispyribac−sodium)、ピノキサデン(pinoxaden)、ビフェノックス(bifenox)、ピペロホス(piperophos)、ピラクロニル(pyraclonil)、ピラスルホトール(pyrasulfotole)、ピラゾキシフェン(pyrazoxyfen)、ピラゾスルフロン・エチル(pyrazosulfuron−ethyl)、ピラゾリネート(pyrazolynate)、ビラナホス(bilanafos)、ピラフルフェン・エチル(pyraflufen−ethyl)、ピリダフォル(pyridafol)、ピリチオバック・ナトリウム塩(pyrithiobac−sodium)、ピリデート(pyridate)、ピリフタリド(pyriftalid)、ピリブチカルブ(pyributicarb)、ピリベンゾキシム(pyribenzoxim)、ピリミスルファン(pyrimisulfan)、ピリミノバック・メチル(pyriminobac−methyl)、ピロキサスルホン(pyroxasulfone)、ピロクススラム(pyroxsulam)、フェニソファム(ph
enisopham)、フェニュロン(fenuron)、フェノキサスルホン(fenoxasulfone)、フェノキサプロップ(fenoxaprop)(メチル、エチル、イソプロピルエステルを含む)、フェノキサプロップ・P(fenoxaprop−P)(メチル、エチル、イソプロピルエステルを含む)、フェンキノトリオン(fenquinotrione)、フェンチアプロップ・エチル(fenthiaprop−ethyl)、フェントラザミド(fentrazamide)、フェンメディファム(phenmedipham)、ホラムスルフロン(foramsulfuron)、ブタクロール(butachlor)、ブタフェナシル(butafenacil)、ブタミホス(butamifos)、ブチレート(butylate)、ブテナクロール(butenachlor)、ブトラリン(butralin)、ブトロキシジム(butroxydim)、フラザスルフロン(flazasulfuron)、フラムプロップ(flamprop)(メチル、エチル、イソプロピルエステルを含む)、フラムプロップ・M(flamprop−M)(メチル、エチル、イソプロピルエステルを含む)、プリミスルフロン・メチル(primisulfuron−methyl)、フルアジホップ・ブチル(fluazifop−butyl)、フルアジホップ・P・ブチル(fluazifop−P−butyl)、フルアゾレート(fluazolate)、フルオメツロン(fluometuron)、フルオログリコフェン・エチル(fluoroglycofen−ethyl)、フルカルバゾン・ナトリウム塩(flucarbazone−sodium)、フルクロラリン(fluchloralin)、フルセトスルフロン(flucetosulfuron)、フルチアセット・メチル(fluthiacet−methyl)、フルピルスルフロン・メチル(flupyrsulfuron−methyl)(ナトリウム、カルシウム又はアンモニアなどの塩を含む)、フルフェナセット(flufenacet)、フルフェンピル・エチル(flufenpyr−ethyl)、フルプロパネート(flupropanate)、フルポキサム(flupoxame)、フルミオキサジン(flumioxazin)、フルミクロラック・ペンチル(flumiclorac−pentyl)、フルメツラム(flumetsulam)、フルリドン(fluridone)、フルルタモン(flurtamone)、フルロキシピル(fluroxypyr)(ブトメチル、メプチル等のエステル体、ナトリウム、カルシウム又はアンモニアなどの塩を含む)、フルロクロリドン(flurochloridone)、プレチラクロール(pretilachlor)、プロカルバゾン・ナトリウム塩(procarbazone−sodium)、プロジアミン(prodiamine)、プロスルフロン(prosulfuron)、プロスルホカルブ(prosulfocarb)、プロパキザホップ(propaquizafop)、プロパクロール(propachlor)、プロパジン(propazine)、プロパニル(propanil)、プロピザミド(propyzamide)、プロピソクロール(propisochlor)、プロピリスルフロン(propyrisulfuron)、プロファム(propham)、プロフルアゾール(profluazol)、プロヘキサジオン・カルシウム塩(prohexadione−calcium)、プロポキシカルバゾン(propoxycarbazone)、プロポキシカルバゾン・ナトリウム塩(propoxycarbazone−sodium)、プロホキシジム(profoxydim)、ブロマシル(bromacil)、ブロムピラゾン(brompyrazon)、プロメトリン(prometryn)、プロメトン(prometon)、ブロモキシニル(bromoxynil)(酪酸、オクタン酸又はヘプタン酸等のエステル体を含む)、ブロモフェノキシム(bromofenoxim)、ブロモブチド(bromobutide)、フロラスラム(florasulam)、フロルピラキシフェン(florpyrauxifen)、フロルピラウキシフェン・ベンジル(florpyrauxifen−benzyl)、ヘキサジノン(hexazinone)、ペトキサミド(pethoxamid)、ベナゾリン(benazolin)、ペノキススラム(penoxsulam)、ヘプタマロキシログルカン(heptamaloxyloglucan)、ベフルブタミド(beflubutamid)、ペブレート(pebulate)、ペラルゴン酸(pelargonic acid)、ベンカルバゾン(bencarbazone)、ペンジメタリン(pendimethalin)、ベンズフェンジゾン(benzfendizone)、ベンスリド(bensulide)、ベンスルフロン・メチル(bensulfuron−methyl)、ベンゾビシクロン(benzobicyclon)、ベンゾフェナップ(benzofenap)、ベンタゾン(bentazone)、ペンタノクロール(pentanochlor)、ペントキサゾン(pentoxazone)、ベンフルラリン(benfluralin)、ベンフレセート(benfuresate)、ホサミン(fosamine)、ホメサフェン(fomesafen)、ホラムスルフロン(foramsulfuron)、ホルクロルフェニュロン(forchlorfenuron)、メコプロップ(mecoprop)(ナトリウム、カリウム、イソプロピルアミン、トリエタノールアミン、ジメチルアミン等の塩を含む)、メコプロップ・P・カリウム塩(mecoprop−P−potassium)、メソスルフロン(mesosulfuron)(メチル等のエステル体含む)、メソトリオン(mesotrione)、メタザクロール(metazachlor)、メタゾスルフロン(metazosulfuron)、メタベンズチアズロン(methabenzthiazuron)、メタミトロン(metamitron)、メタミホップ(metamifop)、メタム(metam)、メタンアルソン酸二ナトリウム(DSMA)、メチオゾリン(methiozolin)、メチルダイムロン(methyldymuron)、メトキスロン(metoxuron)、メトスラム(metosulam)、メトスルフロン・メチル(metsulfuron−methyl)、メトブロムロン(metobromuron)、メトベンズロン(metobenzuron)、メトラクロール(metolachlor)、メトリブジン(metribuzin)、メピコート・クロリド(mepiquat chloride)、メフェナセット(mefenacet)、モノスルフロン(monosulfuron)(メチル、エチル、イソプロピルエステル含む)、モノリニュロン(monolinuron)、モリネート(molinate)、ヨードスルフロン(iodosulfuron)、ヨードスルフロンメチルナトリウム塩(iodosulfulon−methyl−sodium)、ヨーフェンスルフロン(iofensulfuron)、ヨーフェンスルフロン・ナトリウム塩(iofensulfuron−sodium)、ラクトフェン(lactofen)、ランコトリオン(lancotrione)、リニュロン(linuron)、リムスルフロン(rimsulfuron)、レナシル(lenacil)、2,2,2−トリクロロ酢酸(TCA)(ナトリウム、カルシウム又はアンモニアなどの塩を含む)、2,3,6−トリクロロ安息香酸(2,3,6−TBA)、2,4,5−トリクロロフェノキシ酢酸(2,4,5−T)、2,4−ジクロロフェノキシ酢酸(2,4−D)(アミン、ジエチルアミン、トリエタノールアミン、イソプロピルアミン、ナトリウム又はリチウムなどの塩を含む)、2−アミノ−3−クロロ−1,4−ナフトキノン(ACN)、2−メチル−4−クロロフェノキシ酢酸(MCPA)(ナトリウム塩、エチルエステルなどを含む)、2−メチル−4−クロロフェノキシ酪酸(MCPB)(ナトリウム塩、エチルエステルなどを含む)、4−(2,4−ジクロロフェノキシ)酪酸(2,4−DB)、4,6−ジニトロ−O−クレゾール(DNOC)(アミン又はナトリウムなどの塩を含む)、AE−F‐150944(コード番号)、F9600(コード番号)、IR−6396(コード番号)、MCPA・チオエチル(MCPA−thioethyl)、SYP−298(コード番号)、SYP−300(コード番号)、S−エチルジプロピルチオカーバメート(EPTC)、S−メトラクロール(S−metolachlor)、S−9750(コード番号)、MSMA(MSMA)、HW−02(コード番号)。
1−ナフチルアセトアミド(1−naphthylacetamide)、1−メチルシクロプロペン(1−methylcyclopropene)、2,6−ジイソプロピルナフタレン(2,6−diisopropylnaphthalene)、4−オキソ−4−(2−フェニルエチル)アミノ酪酸(化学名、CAS登録番号:1083−55−2)、4−クロロフェノキシ酢酸(4−CPA)、n−デシルアルコール(n−decanol)、アビグリシン(aviglycine)、アンシミドール(ancymidol)、アブシジン酸(abscisic acid)、イナベンフィド(inabenfide)、インドール酢酸(indole acetic acid)、インドール酪酸(indole butyric acid)、ウニコナゾール(uniconazole)、ウニコナゾール−P(uniconazole−P)、エコリスト(Ecolyst)、エチクロゼート(ethychlozate)、エテホン(ethephon)、エポコレオン(epocholeone)、オキシン硫酸塩(oxine−sulfate)、カルボネ(carvone)、ギ酸カルシウム(calcium formate)、クロキシホナック(cloxyfonac)、クロキシホナック・カリウム塩(cloxyfonac−potassium)、クロプロップ(cloprop)、クロルメコート(chlormequat)、コリン(choline)、サイトカイニン(cytokinins)、シクラニリド(cyclanilide)、ジケグラック(dikegulac)、ジベレリン(gibberellin acid)、ジメチピン(dimethipin)、シントフェン(sintofen)、ダミノジット(daminozide)、チジアズロン(thidiazuron)、トリアコンタノール(triacontanol)、トリネキサパック・エチル(trinexapac−ethyl)、パクロブトラゾール(paclobutrazol)、パラフィン(paraffin)、フルメトラリン(flumetralin)、フルルプリミドール(flurprimidol)、フルレノール(flurenol)、プロヒドロジャスモン(prohydrojasmon)、プロヘキサジオン・カルシウム塩(prohexadione−calcium)、ヘプタマロキシログルカン(heptamaloxyloglucan)、ベンジルアミノプリン(benzylaminopurine)、ホルクロルフェニュロン(forchlorfenuron)、マレイン酸ヒドラジド(maleic hydrazide)、メピコート・クロリド(mepiquat chloride)、メフルイジド(mefluidide)、過酸化カルシウム。
4−(2,2,3,3,3−ペンタフルオロプロポキシ)−1−(ピリジン−3−イル)−1H−ピラゾール−3−カルボキサミド(本発明化合物番号:A−0044)の製造
国際公開第2016/027790号の参考例1及び2記載の方法により合成した4−ヒドロキシ−1−(ピリジン−3−イル)−1H−ピラゾール−3−カルボン酸エチル(2.5g、10.7mmoL)、ノナフルオロブタンスルホン酸2,2,3,3,3−ペンタフルオロプロピル(4.7g、10.9mmoL)及び無水炭酸カリウム(1.6g、11.6mmoL)を室温にてジメチルスルホキシド(50mL)に順次加え、更に3時間撹拌した。反応溶液を飽和食塩水に注ぎ、酢酸エチルにて抽出した。得られた有機層を無水硫酸マグネシウムにて乾燥後、減圧下に溶媒を留去した。残渣をシリカゲルカラムクロマトグラフィーにて精製し4−(2,2,3,3,3−ペンタフルオロプロポキシ)−1−(ピリジン−3−イル)−1H−ピラゾール−3−カルボン酸エチル(3.3g、収率:84%)を得た。
1H−NMRデータ(400MHz,CDCl3/TMS δ(ppm)): 1.45(3H, t), 4.47(2H, q), 4.54(2H, t), 7.45(1H, dd), 7.81(1H, s), 8.11(1H, d), 8.63(1H, d), 8.96(1H, d)
4−(2,2,3,3,3−ペンタフルオロプロポキシ)−1−(ピリジン−3−イル)−1H−ピラゾール−3−カルボン酸エチル(1.2g、3.3mmoL)をメタノール(100mL)に溶解し、更にアンモニア水(含量:28%、50mL)を加え室温にて12時間撹拌した。反応溶液の溶媒を減圧下に留去し、残渣をシリカゲルカラムクロマトグラフィーにて精製し4−(2,2,3,3,3−ペンタフルオロプロポキシ)−1−(ピリジン−3−イル)−1H−ピラゾール−3−カルボキサミド(0.8g、収率:72%)を得た。
1H−NMRデータ(400MHz,CDCl3/TMS δ(ppm)): 4.68(2H, t), 5.95(1H, br), 6.81(1H, br), 7.45(1H, dd), 7.91(1H, s), 8.06(1H, d), 8.63(1H, d), 8.97(1H, d)
4−ベンジルオキシ−1−(ピリジン−3−イル)−1H−ピラゾール−3−カルボキサミド(本発明化合物番号:A−0240)の製造
4−ヒドロキシ−1−(ピリジン−3−イル)−1H−ピラゾール−3−カルボン酸エチル(7.5g、32.2mmoL)のN,N−ジメチルホルムアミド(150mL)溶液に、室温下水素化ナトリウム(含量60%、1.5g、37.5mmoL)を少量ずつ加え約30分撹拌した。この反応溶液中に室温下ベンジルブロミド(5.5g、32.2mmoL)を加え1時間反応させた。この反応溶液を飽和食塩水に注ぎ、酢酸エチルにて抽出した。得られた有機層を無水硫酸マグネシウムで乾燥後、減圧下にて溶媒を留去した。得られた固体をヘキサンにて洗浄し、4−ベンジルオキシ−1−(ピリジン−3−イル)−1H−ピラゾール−3−カルボン酸エチル(8.1g、収率:78%)を得た。
1H−NMRデータ(400MHz,CDCl3/TMS δ(ppm)): 1.44(3H, t), 4.47(2H, q), 5.15(2H, s), 7.32−7.48(6H, m), 7.56(1H, s), 8.09(1H, d), 8.58(1H, d), 8.89(1H, d)
4−ベンジルオキシ−1−(ピリジン−3−イル)−1H−ピラゾール−3−カルボン酸エチル(7.5g、23.2mmoL)をエタノール(200mL)に溶解し、水酸化カリウム(10.0g、178.2mmoL)と水(20mL)を室温にて加え1時間撹拌した。この反応溶液の溶媒を減圧下に留去し残渣に6N塩酸を加え、析出した固体を濾取、乾燥し粗製の4−ベンジルオキシ−1−(ピリジン−3−イル)−1H−ピラゾール−3−カルボン酸を得た。得られた4−ベンジルオキシ−1−(ピリジン−3−イル)−1H−ピラゾール−3−カルボン酸をジクロロメタン(200mL)に溶解しオキサリルクロリド(10g、78.8mmoL)及びN,N−ジメチルホルムアミド(触媒量)を加え、室温にて13時間反応させた。溶液を減圧下に留去し、残渣を酢酸エチル(50mL)に溶解した。この溶液を0℃にて酢酸エチル(200mL)とアンモニア水(含量:28%、50mL)の混合溶液に加えた後、室温にて1時間撹拌した。この反応溶液を減圧下に溶媒を留去し、残渣を酢酸エチルにて抽出し無水硫酸マグネシウムで乾燥後溶媒を留去した。得られた固体をヘキサンにて洗浄し4−ベンジルオキシ−1−(ピリジン−3−イル)−1H−ピラゾール−3−カルボキサミド(5.5g、収率:81%)を得た。
1H−NMRデータ(400MHz,CDCl3/TMS δ(ppm)): 6.04(1H, br), 6.95(1H, br), 7.36−7.47(6H, m), 7.63(1H, s), 8.11(1H, d), 8.57(1H, d), 8.90(1H, d)
1−(ピリジン−3−イル)−4−[1,1,2−トリフルオロ−2−(トリフルオロメトキシ)エトキシ]−1H−ピラゾール−3−カルボキサミド(本発明化合物番号:A−0071)の製造
4−ベンジルオキシ−1−(ピリジン−3−イル)−1H−ピラゾール−3−カルボキサミド(1.5g、5.1mmoL)をエタノール(100mL)に溶解しパラジウム活性炭(含量:10%、0.5g)を加え、水素(120mL)を2時間かけて導入した。反応液を濾過し減圧下に溶媒を留去した。残さをヘキサン洗浄し4−ヒドロキシ−1−(ピリジン−3−イル)−1H−ピラゾール−3−カルボキサミド(0.55g、収率:53%)を得た。
1H−NMRデータ(400MHz,DMSO−d6/TMS δ(ppm)): 7.56(1H, dd),7.62(1H, br), 7.69(1H, br), 8.21(1H, s), 8.24(1H, d), 8.54(1H, d), 9.13(1H, d), 9.35(1H, br)
4−ヒドロキシ−1−(ピリジン−3−イル)−1H−ピラゾール−3−カルボキサミド(0.9g、4.4mmoL)をN,N−ジメチルホルムアミド(100mL)及びトリエチルアミン(20mL)の混合溶媒に加えた。この反応溶液中に50℃にて(トリフルオロメチル)(トリフルオロビニル)エーテル(2g、12.0mmoL)を約30分かけて導入し、更に30分間撹拌した。反応終了後溶媒を減圧下に留去した。残渣をシリカゲルカラムクロマトグラフィーにて精製し、1−(ピリジン−3−イル)−4−[1,1,2−トリフルオロ−2−(トリフルオロメトキシ)エトキシ]−1H−ピラゾール−3−カルボキサミド(0.8g、収率:49%)を得た。
1H−NMRデータ(400MHz,CDCl3/TMS δ(ppm)): 5.77(1H, br), 6.17(1H, d), 6.72(1H, br), 7.48(1H, dd), 8.05(1H, s), 8.06(1H, d), 8.67(1H, d), 9.01(1H, d)
4−(3,3−ジメチルブトキシ)−1−(ピリジン−3−イル)−1H−ピラゾール−3−カルボキサミド(本発明化合物番号:A−0017)の製造
4−ヒドロキシ−1−(ピリジン−3−イル)−1H−ピラゾール−3−カルボン酸エチル(1.0g、4.3mmoL)と3,3−ジメチルブタノール(0.53g、5.2mmoL)とトリフェニルホスフィン(1.4g、5.2mmoL)をTHF(50mL)に溶解し、氷冷下にアゾジカルボン酸ジイソプロピル(1.1g、5.2mmoL)を加え室温にて一晩撹拌した。反応終了後、減圧下溶媒を留去し、残渣をシリカゲルカラムクロマトグラフィーにて精製し、4−(3,3−ジメチルブトキシ)−1−(ピリジン−3−イル)−1H−ピラゾール−3−カルボン酸エチル(1.27g、収率:93%)を得た。
1H−NMRデータ(300MHz,CDCl3/TMS δ(ppm)): 1.02(9H, s), 1.42(3H, t), 1.82(2H, t), 4.07(2H, t), 4.44(2H, q), 7.43(1H, dd), 7.62(1H, s), 8.15(1H, d), 8.59(1H, d), 8.96(1H, d)
4−(3,3−ジメチルブトキシ)−1−(ピリジン−3−イル)−1H−ピラゾール−3−カルボン酸エチル(1.1g、3.4mmoL)をエタノール(30mL)に溶解し、水酸化ナトリウム(0.33g、8.4mmoL)と水(20mL)の混合溶液を室温にて加え1時間撹拌した。この反応溶液の溶媒を減圧下に留去し残渣に6N塩酸を加え、酢酸エチルにて抽出し、飽和食塩水で洗浄した。無水硫酸マグネシウムで乾燥後溶媒を留去し、4−(3,3−ジメチルブトキシ)−1−(ピリジン−3−イル)−1H−ピラゾール−3−カルボン酸(0.73g、収率:74%)を得た。
1H−NMRデータ(300MHz,CDCl3/TMS δ(ppm)): 1.03(9H, s), 1.85(2H, t), 4.15(2H, t), 7.49(1H, dd), 7.71(1H, s), 8.23(1H, d), 8.64(1H, d), 9.04(1H, d)
4−(3,3−ジメチルブトキシ)−1−(ピリジン−3−イル)−1H−ピラゾール−3−カルボン酸(0.65g、2.3mmoL)をジクロロメタン(15mL)に溶解しオキサリルクロリド(1mL)及びN,N−ジメチルホルムアミド(触媒量)を加え、40℃にて1時間加熱還流した。溶液を減圧下に留去し、残渣をTHF(20mL)に懸濁した。この溶液を氷冷下にてTHF(15mL)とアンモニア水(含量:28%、20mL)の混合溶液に加えた後、氷冷下にて30分間撹拌した。この反応溶液を減圧下に溶媒を留去し、残渣を水、ヘキサンで順次洗浄後、得られた固体を乾燥し4−(3,3−ジメチルブトキシ)−1−(ピリジン−3−イル)−1H−ピラゾール−3−カルボキサミド(0.45g、収率:69%)を得た。
1H−NMRデータ(300MHz,CDCl3/TMS δ(ppm)): 1.02(9H, s), 1.83(2H, t), 4.14(2H, t), 5.73(1H, br), 6.95(1H, br), 7.42(1H, dd), 7.67(1H, s), 8.18(1H, d), 8.58(1H, d), 8.96(1H, d)
N−イソブチリル−1−(ピリジン−3−イル)−4−[1,1,2−トリフルオロ−2−(トリフルオロメトキシ)エトキシ]−1H−ピラゾール−3−カルボキサミド(本発明化合物番号:A−2403)の製造
1H−NMRデータ(400MHz,CDCl3/TMS δ(ppm)): 1.26(6H, d), 3.56(1H, sext), 6.14(1H, dt), 7.52(1H, dd), 8.05−8.10(2H, m), 8.71(1H, dd), 9.00(1H, d), 9.13(1H, br)
1−(ピリジン−3−イル)−4−[1,1,2−トリフルオロ−2−(トリフルオロメトキシ)エトキシ]−1H−ピラゾール−3−カルボニトリルの製造
1H−NMRデータ(400MHz,CDCl3/TMS δ(ppm)): 6.05(1H, dt), 7.51(1H, m), 8.06−8.10(2H, m), 8.71(1H, dd), 8.98(1H, d)
1−(ピリジン−3−イル)−4−[1,1,2−トリフルオロ−2−(トリフルオロメトキシ)エトキシ]−1H−ピラゾール−3−カルボチオアミド(本発明化合物番号:A−5436)の製造
1H−NMRデータ(400MHz,DMSO−d6/TMS δ(ppm)): 7.17(1H, dt), 7.61(1H, dd), 8.37(1H, d), 8.61(1H, d), 8.96(1H, s), 9.23(1H, d), 9.53(1H, br), 9.88(1H, br)
3−(3−カルバモイル−4−[1,1,2−トリフルオロ−2−(トリフルオロメトキシ)エトキシ]−1H−ピラゾール−1−イル)ピリジン−1−オキシド(本発明化合物番号:A−5510)の製造
1H−NMRデータ(400MHz,DMSO−d6/TMS δ(ppm)): 7.24(1H, d), 7.58(2H, br), 7.93(2H, br), 8.25(1H, s), 9.01(1H, d), 9.05(1H, d)
表1〜表93及び表150〜表155に記載の化合物 10部
シクロヘキサノン 30部
ポリオキシエチレンアルキルアリールエーテル 11部
アルキルベンゼンスルホン酸カルシウム 4部
メチルナフタリン 45部
以上を均一に溶解して乳剤とした。
表1〜表93及び表150〜表155に記載の化合物 10部
ナフタレンスルホン酸ホルマリン縮合物ナトリウム塩 0.5部
ポリオキシエチレンアルキルアリールエーテル 0.5部
珪藻土 24部
クレー 65部
以上を均一に混合粉砕して水和剤とした。
表1〜表93及び表150〜表155に記載の化合物 2部
珪藻土 5部
クレー 93部
以上を均一に混合粉砕して粉剤とした。
表1〜表93及び表150〜表155に記載の化合物 5部
ラウリルアルコール硫酸エステルのナトリウム塩 2部
リグニンスルホン酸ナトリウム 5部
カルボキシメチルセルロース 2部
クレー 86部
以上を均一に混合粉砕した。この混合物に水20部相当量を加えて練り合せ、押出式造粒機を用いて14〜32メッシュの粒状に加工した後、乾燥して粒剤とした。
表1〜表93及び表150〜表155に記載の化合物 20部
ポリオキシエチレンスチレン化フェニルエーテル硫酸塩 4部
エチレングリコール 7部
シリコーンAF−118N(旭化成工業株式会社製) 0.02部
水 68.98部
以上を高速攪拌機にて30分間混合した後、湿式粉砕機にて粉砕しフロアブル剤とした。
表1〜表93及び表150〜表155に記載の化合物 10部
リグニンスルホン酸ナトリウム 5部
ポリオキシエチレンアルキルアリールエーテル 1部
ポリカルボン酸ナトリウム 3部
ホワイトカーボン 5部
α化デンプン 1部
炭酸カルシウム 65部
水 10部
以上を混合練り押し造粒した。得られた粒状物を流動層乾燥機で乾燥し、顆粒水和剤を得た。
製造例2に準じて調製した水和剤を、有効成分として500ppmの濃度に水で希釈した。この薬液にキャベツ葉を浸漬し、風乾後、プラスチックカップに入れた。その中にコナガ2齢幼虫10頭を放ち、蓋をした。その後、25℃の恒温室に置き、6日後に死虫数を調査し数1の計算式により死虫率を求めた。試験は1連制で行った。
A−0001、A−0006、A−0008A、A−0009、A−0010、A−0015、A−0015、A−0028、A−0067、A−0082、A−0083、A−0098、A−0100、A−0111、A−0120、A−0125、A−0144、A−0145、A−0165、A−0177、A−0197、A−0203、A−0211、A−0212、A−0225、A−0234、A−0246、A−0247、A−0248、A−0254、A−0283、A−1106、A−1120、A−1302、A−1368、A−1429、A−1443、A−1684、A−1948、A−2014、A−2164、A−2337、A−2403、A−2469、A−2535、A−2610、A−2858、A−2924、A−2990、A−3056、A−3188、A−3254、A−3320、A−3386、A−3452、A−3518、A−3584、A−3650、A−3716、A−3791、A−3973、A−4257、B−0006、B−0009、B−0010、B−0013、B−0014、B−0015、B−0016、B−0017、B−0043、B−0050、B−0051、B−0068、B−0083、B−0093、B−0098、B−0100、B−0137、B−0246、B−0247、B−0253、B−0254、B−0263、B−0264、B−0267、B−0269、B−0270、B−0271、B−0275、B−0285、B−0286、B−0332、B−0336、B−0337、B−0347、B−0354、B−0357、B−0360、B−0374、B−0375、B−0376、B−0379、B−0405、B−0438、B−0446、B−0465、B−0500、B−0503、B−0507、B−0508、B−0727、B−01088、B−01474、B−02300
製造例2に準じて調製した水和剤を、有効成分として500ppmの濃度に水で希釈した。この薬液にキャベツ葉を浸漬し、風乾後、プラスチックカップに入れた。その中にオオタバコガ孵化幼虫5頭を放ち、蓋をした。その後、25℃の恒温室に置き、6日後に死虫数を調査し数1の計算式により死虫率を求めた。試験は2連制で行った。
A−0004、A−0006、A−0018、A−0043、A−0045、A−0052、A−0058、A−0061、A−0062、A−0065、A−0067、A−0073、A−0145、A−0151、A−0186、A−0246、A−1106、A−1429、A−1443、A−1625、A−3122、A−3254、A−3320、A−3791、A−3973、A−4257、A−4304、A−5436、B−0004、B−0006、B−0016、B−0043、B−0045、B−0056、B−0065、B−0067、B−0088、B−0089、B−0095、B−0153、B−0165、B−0192、B−0246、B−0256、B−0276、B−02786、B−0297、B−0299、B−0300、B−0312、B−0316、B−0319、B−0321、B−0334、B−0340、B−0348、B−0349、B−0360、B−0405、B−0407、B−0471、B−0475、B−0500、B−0508、B−0891、B−1133、B−1667、B−2300
製剤例2に準じて調製した水和剤を、有効成分として500ppmの濃度に水で希釈した。この薬液に、予めワタアブラムシ若虫を接種しておいたキュウリ苗を浸漬し、風乾した。処理後のキュウリ苗は25℃の恒温室に置き、3日後に生存虫数を数え、数1の計算式により死虫率を求めた。試験は1連制で行った。
A−0001、A−0002、A−0003、A−0004、A−0005、A−0006、A−0007、A−0008、A−0009、A−0010、A−0011、A−0012、A−0013、A−0014、A−0015、A−0017、A−0018、A−0019、A−0020、A−0027、A−0028、A−0031、A−00、A−0034、A−0043、A−0044、A−0045、A−0046、A−0047、A−0050、A−0051、A−0052、A−0053、A−0056、A−0058、A−0060、A−0061、A−0062、A−0065、A−0067、A−0070、A−0071、A−0072、A−0073、A−0075、A−0076、A−0077、A−0078、A−0080、A−0081、A−0083、A−0086、A−0088、A−0092、A−0093、A−0094、A−0098、A−0100、A−0103、A−0105、A−0106、A−0111、A−0113、A−0122、A−0151、A−0152、A−0153、A−0165、A−0186、A−0221、A−0225、A−0234、A−0240、A−0249、A−0253、A−0254、A−0283、A−0468、A−0658、A−0849、A−1045、A−1106、A−1120、A−1302、A−1368、A−1429、A−1443、A−1625、A−1684、A−1686、A−1700、A−1882、A−1948、A−2014、A−2080、A−2155、A−2164、A−2337、A−2403、A−2469、A−2535、A−2610、A−2792、A−2858、A−2924、A−2990、A−3056、A−3122、A−3188、A−3254、A−3320、A−3386、A−3452、A−3518、A−3584、A−3650、A−3716、A−3791、A−3973、A−4095、A−4304、A−5436、A−5510
製剤例2に準じて調製した水和剤を、有効成分として500ppmの濃度に水で希釈した。この薬液に、イネの籾を浸漬し、プラスチックカップに入れた。このプラスチックカップにトビイロウンカ2齢幼虫を10頭放ち、蓋をして25℃の恒温室に置いた。6日後に生存虫数を数え、数1の計算式により死虫率を求めた。試験は1連制で行った。
A−0002、A−0003、A−0004、A−0005、A−0006、A−0007、A−0009、A−0010、A−0011、A−0013、A−0015、A−0016、A−0017、A−0018、A−0019、A−0020、A−0021、A−0022、A−27、A−0028、A−0032、A−0034、A−0043、A−0045、A−0046、A−0047、A−0051、A−0052、A−0056、A−0058、A−0060、A−0062、A−0067、A−0070、A−0071、A−0073、A−0075、A−0076、A−0078、A−0080、A−0081、A−0081、A−0082、A−0083、A−0089、A−0092、A−0093、A−0094、A−0095、A−0098、A−0100、A−0103、A−0105、A−0113、A−0120、A−0121、A−01222、A−0125、A−0126、A−0135、A−0136、A−0137、A−0144、A−0145、A−0151、A−0153、A−0165、A−0166、A−0177、A−0186、A−0209、A−0211、A−0217、A−0221、A−0234、A−0246、A−0247、A−0248、A−0249、A−0253、A−0254、A−0283、A−0468、A−0658、A−1045、A−1106、A−1120、A−1368、A−1443、A−1625、A−1684、A−1700、A−1882、A−1948、A−2014、A−2080、A−2155、A−2164、A−2337、A−2403、A−2469、A−2990、A−3056、A−3122、A−3188、A−3320、A−3386、A−3452、A−3518、A−3584、A−3650、A−3973、A−4095、A−4257、A−5436、A−5510、B−0004、B−0009、B−0010、B−0011、B−0015、B−0016、B−0017、B−0021、B−0022、B−0045、B−0046、B−0058、B−0062、B−0067、B−0075、B−0081、B−0082、B−0083、B−0093、B−0100、B−0105、B−0121、B−0151、B−0257、B−0258、B−0259、B−0260、B−0262、B−0263、B−0264、B−0265、B−0268、B−0269、B−0270、B−0271、B−0273、B−0274、B−0275、B−0276、B−0285、B−0286、B−0297、B−0299、B−0300、B−0305、B−0306、B−0312、B−0314、B−0316、B−0329、B−0332、B−0336、B−0337、B−0342、B−0352、B−0354、B−0357、B−0359、B−0361、B−0367、B−0374、B−0375、B−0378、B−0379、B−0380、B−0390、B−0405、B−0407、B−0419、B−0420、B−0463、B−0465、B−0507、B−0727、B−1133
Claims (15)
- 一般式[I]
nは、0又は1の整数を示し、
Xは、酸素原子又は硫黄原子を示し、
R1、R2、R3、R4及びR5は、各々独立して水素原子、ハロゲン原子、C1〜C6アルキル基、C1〜C6ハロアルキル基、C1〜C6アルコキシ基、C1〜C6ハロアルコキシ基、C3〜C6シクロアルキル基、C1〜C6アルキルチオ基、C1〜C6アルキルスルフィニル基、C1〜C6アルキルスルホニル基、アミノ基、モノ(C1〜C6アルキル)アミノ基、ジ(C1〜C6アルキル)アミノ基、シアノ基又はニトロ基を示し、
R6は、水素原子、C1〜C12アルキル基、C1〜C6アルコキシC1〜C6アルキル基、C1〜C12ハロアルキル基、C1〜C6アルコキシC1〜C6ハロアルキル基、C1〜C6ハロアルコキシC1〜C6アルキル基、C1〜C6ハロアルコキシC1〜C6ハロアルキル基、C2〜C7アルキニル基、C3〜C6シクロアルキルC2〜C6アルキニル基、C2〜C6ハロアルキニル基、C2〜C6アルケニル基、C2〜C6ハロアルケニル基、C3〜C6シクロアルキル基、C3〜C6ハロシクロアルキル基、C1〜C6ハロアルキルC3〜C6シクロアルキル基、C3〜C6シクロアルキルC1〜C6アルキル基、C3〜C6ハロシクロアルキルC1〜C6アルキル基、C1〜C6アルキルチオC1〜C6アルキル基、C1〜C6アルキルスルフィニルC1〜C6アルキル基、C1〜C6アルキルスルホニルC1〜C6アルキル基、C1〜C6ハロアルキルチオC1〜C6アルキル基、C1〜C6ハロアルキルスルフィニルC1〜C6アルキル基、C1〜C6ハロアルキルスルホニルC1〜C6アルキル基、C1〜C6アルキルカルボニルC1〜C6アルキル基、C1〜C6ハロアルキルカルボニルC1〜C6アルキル基、C1〜C6アルコキシカルボニルC1〜C6アルキル基、アミノカルボニルC1〜C6アルキル基、モノ(C1〜C6アルキル)アミノカルボニルC1〜C6アルキル基、モノ(C3〜C6シクロアルキル)アミノカルボニルC1〜C6アルキル基、モノ(C1〜C6ハロアルキル)アミノカルボニルC1〜C6アルキル基、ジ(C1〜C6アルキル)アミノカルボニルC1〜C6アルキル基、モノ(C1〜C6アルキルカルボニル)アミノC1〜C6アルキル基、モノ(C1〜C6アルコキシカルボニル)アミノC1〜C6アルキル基、モノ(C1〜C6アルキルスルホニル)アミノC1〜C6アルキル基、モノ(C1〜C6ハロアルキルスルホニル)アミノC1〜C6アルキル基、ヒドロキシC1〜C6アルキル基、ヒドロキシイミノC1〜C6アルキル基、C1〜C6アルコキシイミノC1〜C6アルキル基、C1〜C6ハロアルコキシイミノC1〜C6アルキル基又は無置換の若しくはR9で置換されたC7〜C13アラルキル基を示し、
R7及びR8は、各々独立して水素原子、C1〜C6アルキル基、C3〜C6シクロアルキル基、C3〜C6シクロアルキルC1〜C6アルキル基、C2〜C7アルキニル基、C2〜C6アルケニル基、ヒドロキシ基、C1〜C6アルコキシ基、C1〜C6アルコキシC1〜C6アルキル基、C1〜C6ハロアルキル基、2−テトラヒドロフラニル基、3−テトラヒドロフラニル基、2−テトラヒドロピラニル基、4−テトラヒドロピラニル基、シアノC1〜C6アルキル基、シアノC3〜C6シクロアルキル基、ヒドロキシC1〜C6アルキル基、ホルミル基、アミノ基、モノ(C1〜C6アルキル)アミノ基、ジ(C1〜C6アルキル)アミノ基、C1〜C6アルキルカルボニル基、C1〜C6アルコキシC1〜C6アルキルカルボニル基、C3〜C6シクロアルキルカルボニル基、C3〜C6シクロアルキルC1〜C6アルキルカルボニル基、C1〜C6アルコキシカルボニル基、カルバモイル基、モノ(C1〜C6アルキル)アミノカルボニル基、ジ(C1〜C6アルキル)アミノカルボニル基、無置換の若しくはR9で置換されたフェニルカルボニル基、無置換の若しくはR9で置換されたC7〜C13アラルキルカルボニル基、無置換の若しくはR9で置換されたピリジルカルボニル基、無置換の若しくはR9で置換されたピラゾリルカルボニル基、(C1〜C6アルキル)チオカルボニル基、(C1〜C6アルコキシ)チオカルボニル基、チオカルバモイル基、モノ(C1〜C6アルキル)アミノチオカルボニル基、ジ(C1〜C6アルキル)アミノチオカルボニル基、C1〜C6アルキルスルホニル基、スルファモイル基、モノ(C1〜C6アルキル)アミノスルホニル基、ジ(C1〜C6アルキル)アミノスルホニル基、R10R11N−C1〜C6アルキル基、C1〜C6アルコキシカルボニルC1〜C6アルキル基、アミノカルボニルC1〜C6アルキル基、モノ(C1〜C6アルキル)アミノカルボニルC1〜C6アルキル基、モノ(C3〜C6シクロアルキル)アミノカルボニルC1〜C6アルキル基、モノ(C1〜C6ハロアルキル)アミノカルボニルC1〜C6アルキル基、ジ(C1〜C6アルキル)アミノカルボニルC1〜C6アルキル基、ヒドロキシイミノ基、C1〜C6アルコキシイミノ基、ヒドロキシイミノC1〜C6アルキル基、C1〜C6アルコキシイミノC1〜C6アルキル基、を示し、さらに、R7とR8は一緒になって=CR12N(R13)R14または=CR12OR15を形成してもよく、さらに、R7とR8はこれらの結合する炭素原子と共に3〜6員の炭素環、又は酸素原子、硫黄原子及び窒素原子により選択される1〜4個のヘテロ原子を有する3〜6員の複素環を形成してもよく、該複素環はハロゲン原子、シアノ基、ニトロ基、C1〜C6アルキル基、C1〜C6アルコキシ基、C1〜C6ハロアルキル基又はオキソ基によって置換されてもよく、
R9は、ハロゲン原子、C1〜C6アルキル基、C1〜C6ハロアルキル基、C1〜C6アルコキシ基、C1〜C6ハロアルコキシ基、C1〜C6アルキルチオ基、C1〜C6アルキルスルフィニル基、C1〜C6アルキルスルホニル基、C1〜C6ハロアルキルチオ基、C1〜C6ハロアルキルスルフィニル基、C1〜C6ハロアルキルスルホニル基、アミノ基、モノ(C1〜C6アルキル)アミノ基、ジ(C1〜C6アルキル)アミノ基、シアノ基又はニトロ基を示し、
R10及びR11は、各々独立して水素原子、C1〜C6アルキル基、、C1〜C6ハロアルキル基又はC3〜C6シクロアルキル基を示し、さらに、R10とR11はこれらの結合する炭素原子と共に3〜6員環を形成してもよく、
R12は、水素原子、C1〜C6アルキル基、C3〜C6シクロアルキル基を示し、
R13及びR14は、各々独立して水素原子、C1〜C6アルキル基、、C1〜C6ハロアルキル基、C3〜C6シクロアルキル基、C1〜C6アルコキシ基を示し、さらに、R13とR14はこれらの結合する炭素原子と共に3〜6員の炭素環、又は酸素原子、硫黄原子及び窒素原子により選択される1〜4個のヘテロ原子を有する3〜6員の複素環を形成してもよく、
R15は、C1〜C6アルキル基を示す。]
で表されるピラゾール−3−カルボン酸アミド誘導体、又はその農業上許容される塩。 - 一般式[II]
nは、0又は1の整数を示し、
R1、R2、R3、R4及びR5は、各々独立して水素原子、ハロゲン原子、C1〜C6アルキル基、C1〜C6ハロアルキル基、C1〜C6アルコキシ基、C1〜C6ハロアルコキシ基、C3〜C6シクロアルキル基、C1〜C6アルキルチオ基、C1〜C6アルキルスルフィニル基、C1〜C6アルキルスルホニル基、アミノ基、モノ(C1〜C6アルキル)アミノ基、ジ(C1〜C6アルキル)アミノ基、シアノ基又はニトロ基を示し、
R6は、水素原子、C1〜C12アルキル基、C1〜C6アルコキシC1〜C6アルキル基、C1〜C12ハロアルキル基、C1〜C6アルコキシC1〜C6ハロアルキル基、C1〜C6ハロアルコキシC1〜C6アルキル基、C1〜C6ハロアルコキシC1〜C6ハロアルキル基、C2〜C7アルキニル基、C3〜C6シクロアルキルC2〜C6アルキニル基、C2〜C6ハロアルキニル基、C2〜C6アルケニル基、C2〜C6ハロアルケニル基、C3〜C6シクロアルキル基、C3〜C6ハロシクロアルキル基、C1〜C6ハロアルキルC3〜C6シクロアルキル基、C3〜C6シクロアルキルC1〜C6アルキル基、C3〜C6ハロシクロアルキルC1〜C6アルキル基、C1〜C6アルキルチオC1〜C6アルキル基、C1〜C6アルキルスルフィニルC1〜C6アルキル基、C1〜C6アルキルスルホニルC1〜C6アルキル基、C1〜C6ハロアルキルチオC1〜C6アルキル基、C1〜C6ハロアルキルスルフィニルC1〜C6アルキル基、C1〜C6ハロアルキルスルホニルC1〜C6アルキル基、C1〜C6アルキルカルボニルC1〜C6アルキル基、C1〜C6ハロアルキルカルボニルC1〜C6アルキル基、C1〜C6アルコキシカルボニルC1〜C6アルキル基、アミノカルボニルC1〜C6アルキル基、モノ(C1〜C6アルキル)アミノカルボニルC1〜C6アルキル基、モノ(C3〜C6シクロアルキル)アミノカルボニルC1〜C6アルキル基、モノ(C1〜C6ハロアルキル)アミノカルボニルC1〜C6アルキル基、ジ(C1〜C6アルキル)アミノカルボニルC1〜C6アルキル基、モノ(C1〜C6アルキルカルボニル)アミノC1〜C6アルキル基、モノ(C1〜C6アルコキシカルボニル)アミノC1〜C6アルキル基、モノ(C1〜C6アルキルスルホニル)アミノC1〜C6アルキル基、モノ(C1〜C6ハロアルキルスルホニル)アミノC1〜C6アルキル基、ヒドロキシC1〜C6アルキル基、ヒドロキシイミノC1〜C6アルキル基、C1〜C6アルコキシイミノC1〜C6アルキル基、C1〜C6ハロアルコキシイミノC1〜C6アルキル基、無置換の又はR9で置換されたC7〜C13アラルキル基、を示し、
R16は水素原子又はC1〜C6アルキル基を示す。]
で表されるピラゾール−3−カルボン酸誘導体、又はその塩。 - R6が、C1〜C12アルキル基、C1〜C6アルコキシC1〜C6アルキル基、C1〜C12ハロアルキル基、C1〜C6アルコキシC1〜C6ハロアルキル基、C1〜C6ハロアルコキシC1〜C6アルキル基、C1〜C6ハロアルコキシC1〜C6ハロアルキル基、C2〜C7アルキニル基、C3〜C6シクロアルキルC2〜C6アルキニル基、C2〜C6ハロアルキニル基、C2〜C6アルケニル基、C2〜C6ハロアルケニル基、C3〜C6シクロアルキル基、C3〜C6ハロシクロアルキル基、C1〜C6ハロアルキルC3〜C6シクロアルキル基、C3〜C6シクロアルキルC1〜C6アルキル基、C3〜C6ハロシクロアルキルC1〜C6アルキル基、C1〜C6アルキルチオC1〜C6アルキル基、C1〜C6アルキルスルフィニルC1〜C6アルキル基、C1〜C6アルキルスルホニルC1〜C6アルキル基、C1〜C6ハロアルキルチオC1〜C6アルキル基、C1〜C6ハロアルキルスルフィニルC1〜C6アルキル基、C1〜C6ハロアルキルスルホニルC1〜C6アルキル基、C1〜C6アルキルカルボニルC1〜C6アルキル基、C1〜C6ハロアルキルカルボニルC1〜C6アルキル基、C1〜C6アルコキシカルボニルC1〜C6アルキル基、アミノカルボニルC1〜C6アルキル基、モノ(C1〜C6アルキル)アミノカルボニルC1〜C6アルキル基、モノ(C3〜C6シクロアルキル)アミノカルボニルC1〜C6アルキル基、モノ(C1〜C6ハロアルキル)アミノカルボニルC1〜C6アルキル基、ジ(C1〜C6アルキル)アミノカルボニルC1〜C6アルキル基、モノ(C1〜C6アルキルカルボニル)アミノC1〜C6アルキル基、モノ(C1〜C6アルコキシカルボニル)アミノC1〜C6アルキル基、モノ(C1〜C6アルキルスルホニル)アミノC1〜C6アルキル基、モノ(C1〜C6ハロアルキルスルホニル)アミノC1〜C6アルキル基、ヒドロキシC1〜C6アルキル基、ヒドロキシイミノC1〜C6アルキル基、C1〜C6アルコキシイミノC1〜C6アルキル基、C1〜C6ハロアルコキシイミノC1〜C6アルキル基又は無置換の若しくはR9で置換されたC7〜C13アラルキル基で示される請求項1に記載のピラゾール−3−カルボン酸アミド誘導体、又はその農業上許容される塩。
- R6が、C1〜C12アルキル基、C1〜C6アルコキシC1〜C6アルキル基、C1〜C12ハロアルキル基、C1〜C6アルコキシC1〜C6ハロアルキル基、C1〜C6ハロアルコキシC1〜C6アルキル基、C1〜C6ハロアルコキシC1〜C6ハロアルキル基、C2〜C7アルキニル基、C3〜C6シクロアルキルC2〜C6アルキニル基、C2〜C6ハロアルキニル基、C2〜C6アルケニル基、C2〜C6ハロアルケニル基、C3〜C6シクロアルキル基、C3〜C6ハロシクロアルキル基、C1〜C6ハロアルキルC3〜C6シクロアルキル基、C3〜C6シクロアルキルC1〜C6アルキル基、C3〜C6ハロシクロアルキルC1〜C6アルキル基、C1〜C6アルキルチオC1〜C6アルキル基、C1〜C6アルキルスルフィニルC1〜C6アルキル基、C1〜C6アルキルスルホニルC1〜C6アルキル基、C1〜C6ハロアルキルチオC1〜C6アルキル基、C1〜C6ハロアルキルスルフィニルC1〜C6アルキル基、C1〜C6ハロアルキルスルホニルC1〜C6アルキル基、C1〜C6アルキルカルボニルC1〜C6アルキル基、C1〜C6ハロアルキルカルボニルC1〜C6アルキル基、C1〜C6アルコキシカルボニルC1〜C6アルキル基、アミノカルボニルC1〜C6アルキル基、モノ(C1〜C6アルキル)アミノカルボニルC1〜C6アルキル基、モノ(C3〜C6シクロアルキル)アミノカルボニルC1〜C6アルキル基、モノ(C1〜C6ハロアルキル)アミノカルボニルC1〜C6アルキル基、ジ(C1〜C6アルキル)アミノカルボニルC1〜C6アルキル基、モノ(C1〜C6アルキルカルボニル)アミノC1〜C6アルキル基、モノ(C1〜C6アルコキシカルボニル)アミノC1〜C6アルキル基、モノ(C1〜C6アルキルスルホニル)アミノC1〜C6アルキル基、モノ(C1〜C6ハロアルキルスルホニル)アミノC1〜C6アルキル基、ヒドロキシC1〜C6アルキル基、ヒドロキシイミノC1〜C6アルキル基、C1〜C6アルコキシイミノC1〜C6アルキル基、C1〜C6ハロアルコキシイミノC1〜C6アルキル基又は無置換の若しくはR9で置換されたC7〜C13アラルキル基で示される請求項2に記載のピラゾール−3−カルボン酸誘導体、又はその塩。
- 請求項1若しくは3に記載のピラゾール−3−カルボン酸アミド誘導体、若しくはその農業上許容される塩、又は請求項2若しくは4に記載のピラゾール−3−カルボン酸誘導体、若しくはその農業上許容される塩を有効成分として含有する農薬組成物。
- 農薬組成物が、さらに界面活性剤を含有する請求項5に記載の農薬組成物。
- 請求項1若しくは3に記載のピラゾール−3−カルボン酸アミド誘導体、若しくはその農業上許容される塩、又は請求項2若しくは4に記載のピラゾール−3−カルボン酸誘導体、若しくはその農業上許容される塩を活性成分として含有する有害生物防除剤。
- 殺虫剤である請求項7に記載の有害生物防除剤。
- 農園芸用植物を栽培する畑地又は水田における有害生物に対して、防除効力を有する請求項7に記載の有害生物防除剤。
- 農園芸用植物が、育種法又は遺伝子組換え技術により耐性を付与された植物である請求項9に記載の有害生物防除剤。
- 請求項1若しくは3に記載のピラゾール−3−カルボン酸アミド誘導体、若しくはその農業上許容される塩、又は請求項2若しくは4に記載のピラゾール−3−カルボン酸誘導体、若しくはその農業上許容される塩の有効成分量を使用する有害生物の防除方法。
- 請求項1若しくは3に記載のピラゾール−3−カルボン酸アミド誘導体、若しくはその農業上許容される塩、又は請求項2若しくは4に記載のピラゾール−3−カルボン酸誘導体、若しくはその農業上許容される塩を有効成分として含有する農薬組成物を、農園芸用作物または農園芸用作物を生育させようとする若しくは生育している場所に対して、同時に又は分割して作用させることによる、有害生物の防除方法。
- 有害生物防除剤を施用する場所が、水田、畑地、芝地、果樹園、非農耕地、温室、育苗施設、植物工場である請求項11または12に記載の有害生物の防除方法。
- ピラゾール−3−カルボン酸アミド誘導体、又はその農業上許容される塩を殺虫剤として使用する請求項11〜13のいずれか一項に記載の有害生物の防除方法。
- 請求項7〜10のいずれか一項に記載の有害生物防除剤を、農園芸用作物に対する有害生物を防除に使用する記載の有害生物防除剤の使用方法。
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EP3623365B1 (en) | 2023-01-04 |
CN110612295A (zh) | 2019-12-24 |
TW201900645A (zh) | 2019-01-01 |
JP7058265B2 (ja) | 2022-04-21 |
US11993578B2 (en) | 2024-05-28 |
EP3623365A1 (en) | 2020-03-18 |
WO2018207847A1 (ja) | 2018-11-15 |
CN110612295B (zh) | 2023-07-14 |
EP3623365A4 (en) | 2020-12-30 |
TWI771418B (zh) | 2022-07-21 |
US20200199096A1 (en) | 2020-06-25 |
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