JP2010065026A - ピリジル−トリアゾロピリミジン誘導体又はその塩、並びにそれらを含有する有害生物防除剤 - Google Patents

ピリジル−トリアゾロピリミジン誘導体又はその塩、並びにそれらを含有する有害生物防除剤 Download PDF

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Publication number: JP2010065026A
Authority: JP; Japan
Prior art keywords: alkyl; compound; reaction; salt; optionally substituted
Prior art date: 2008-08-13
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Pending

Application number

JP2009186570A

Other languages

English (en)

Japanese (ja)

Inventor

Takahiro Haga

隆弘芳賀

Hirohiko Kimura

博彦木村

Masayuki Morita

雅之森田

Takeshi Ueda

剛上田

Toshihiko Ueki

寿彦植木

Kazuhisa Kiriyama

和久桐山

Kotaro Yoshida

幸太郎吉田

卓 ▲濱▼本

Taku Hamamoto

Tetsuya Kodama

哲也小玉

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Ishihara Sangyo Kaisha Ltd

Original Assignee

Ishihara Sangyo Kaisha Ltd

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

2008-08-13

Filing date

2009-08-11

Publication date

2010-03-25

2009-08-11 Application filed by Ishihara Sangyo Kaisha Ltd filed Critical Ishihara Sangyo Kaisha Ltd

2009-08-11 Priority to JP2009186570A priority Critical patent/JP2010065026A/ja

2010-03-25 Publication of JP2010065026A publication Critical patent/JP2010065026A/ja

Status Pending legal-status Critical Current

Links

150000003839 salts Chemical class 0.000 title claims abstract description 35
230000001473 noxious effect Effects 0.000 title abstract 4
125000000217 alkyl group Chemical group 0.000 claims abstract description 62
125000005843 halogen group Chemical group 0.000 claims abstract description 31
125000003118 aryl group Chemical group 0.000 claims abstract description 27
125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 25
125000001188 haloalkyl group Chemical group 0.000 claims abstract description 25
125000003342 alkenyl group Chemical group 0.000 claims abstract description 24
125000000623 heterocyclic group Chemical group 0.000 claims abstract description 23
125000000304 alkynyl group Chemical group 0.000 claims abstract description 20
125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 16
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 14
241000607479 Yersinia pestis Species 0.000 claims description 61
239000003795 chemical substances by application Substances 0.000 claims description 57
238000000034 method Methods 0.000 claims description 30
239000004480 active ingredient Substances 0.000 claims description 20
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 18
239000002917 insecticide Substances 0.000 claims description 12
239000002689 soil Substances 0.000 claims description 11
230000000895 acaricidal effect Effects 0.000 claims description 9
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 9
239000000642 acaricide Substances 0.000 claims description 8
239000005645 nematicide Substances 0.000 claims description 7
YWBFPKPWMSWWEA-UHFFFAOYSA-O triazolopyrimidine Chemical class BrC1=CC=CC(C=2N=C3N=CN[N+]3=C(NCC=3C=CN=CC=3)C=2)=C1 YWBFPKPWMSWWEA-UHFFFAOYSA-O 0.000 claims description 7
125000004966 cyanoalkyl group Chemical group 0.000 claims description 6
125000004183 alkoxy alkyl group Chemical group 0.000 claims description 5
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
125000004076 pyridyl group Chemical group 0.000 claims description 2
150000003230 pyrimidines Chemical class 0.000 claims description 2
230000000694 effects Effects 0.000 abstract description 9
150000001875 compounds Chemical class 0.000 description 175
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 152
238000006243 chemical reaction Methods 0.000 description 114
-1 1,3-butadienyl Chemical group 0.000 description 108
239000002904 solvent Substances 0.000 description 75
238000004519 manufacturing process Methods 0.000 description 63
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 59
239000000203 mixture Substances 0.000 description 56
230000015572 biosynthetic process Effects 0.000 description 49
238000003786 synthesis reaction Methods 0.000 description 49
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 34
239000000243 solution Substances 0.000 description 34
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 33
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 30
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ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 27
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239000003480 eluent Substances 0.000 description 25
238000010898 silica gel chromatography Methods 0.000 description 25
239000011259 mixed solution Substances 0.000 description 24
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 22
241000238876 Acari Species 0.000 description 21
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 21
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YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 20
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 20
230000003071 parasitic effect Effects 0.000 description 20
239000000047 product Substances 0.000 description 20
241001465754 Metazoa Species 0.000 description 19
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239000002585 base Substances 0.000 description 18
239000013078 crystal Substances 0.000 description 18
239000012044 organic layer Substances 0.000 description 18
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 17
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 16
229920003171 Poly (ethylene oxide) Polymers 0.000 description 16
230000035484 reaction time Effects 0.000 description 16
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
238000009472 formulation Methods 0.000 description 15
238000012360 testing method Methods 0.000 description 15
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 14
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 14
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical class CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 13
239000002671 adjuvant Substances 0.000 description 13
241000238631 Hexapoda Species 0.000 description 12
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 12
241000244206 Nematoda Species 0.000 description 11
238000010992 reflux Methods 0.000 description 11
239000000126 substance Substances 0.000 description 11
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 10
229910052783 alkali metal Inorganic materials 0.000 description 10
LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 10
239000007787 solid Substances 0.000 description 10
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KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
235000014113 dietary fatty acids Nutrition 0.000 description 9
239000000194 fatty acid Substances 0.000 description 9
229930195729 fatty acid Natural products 0.000 description 9
230000002140 halogenating effect Effects 0.000 description 9
239000007788 liquid Substances 0.000 description 9
239000000575 pesticide Substances 0.000 description 9
238000002360 preparation method Methods 0.000 description 9
125000001424 substituent group Chemical group 0.000 description 9
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 8
238000005160 1H NMR spectroscopy Methods 0.000 description 8
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 8
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 8
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 8
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 8
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
241000258242 Siphonaptera Species 0.000 description 8
244000078703 ectoparasite Species 0.000 description 8
150000002170 ethers Chemical class 0.000 description 8
239000003208 petroleum Substances 0.000 description 8
229920006395 saturated elastomer Polymers 0.000 description 8
HVTLNXNGWZPLCU-UHFFFAOYSA-N C1=C(C=NC(=C1Cl)C2=CC(=NC3=NC=NN23)C=O)C(F)(F)F Chemical compound C1=C(C=NC(=C1Cl)C2=CC(=NC3=NC=NN23)C=O)C(F)(F)F HVTLNXNGWZPLCU-UHFFFAOYSA-N 0.000 description 7
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 7
241001674048 Phthiraptera Species 0.000 description 7
SRNKZYRMFBGSGE-UHFFFAOYSA-N [1,2,4]triazolo[1,5-a]pyrimidine Chemical class N1=CC=CN2N=CN=C21 SRNKZYRMFBGSGE-UHFFFAOYSA-N 0.000 description 7
239000003905 agrochemical Substances 0.000 description 7
150000008282 halocarbons Chemical class 0.000 description 7
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 7
JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 7
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 6
DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 6
OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 6
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 6
241000193830 Bacillus <bacterium> Species 0.000 description 6
QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 6
241000258924 Ctenocephalides felis Species 0.000 description 6
240000008067 Cucumis sativus Species 0.000 description 6
235000010799 Cucumis sativus var sativus Nutrition 0.000 description 6
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
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244000000054 animal parasite Species 0.000 description 6
NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 description 6
239000000843 powder Substances 0.000 description 6
239000011541 reaction mixture Substances 0.000 description 6
239000011734 sodium Substances 0.000 description 6
229910052708 sodium Inorganic materials 0.000 description 6
235000015424 sodium Nutrition 0.000 description 6
229910000030 sodium bicarbonate Inorganic materials 0.000 description 6
235000017557 sodium bicarbonate Nutrition 0.000 description 6
WQDUMFSSJAZKTM-UHFFFAOYSA-N sodium methoxide Substances [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 6
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
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DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 5
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239000012046 mixed solvent Substances 0.000 description 5
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230000002792 vascular Effects 0.000 description 1
230000035899 viability Effects 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
229920002554 vinyl polymer Polymers 0.000 description 1
235000013343 vitamin Nutrition 0.000 description 1
239000011782 vitamin Substances 0.000 description 1
229930003231 vitamin Natural products 0.000 description 1
229940088594 vitamin Drugs 0.000 description 1
235000012431 wafers Nutrition 0.000 description 1
229940100445 wheat starch Drugs 0.000 description 1
239000000230 xanthan gum Substances 0.000 description 1
229920001285 xanthan gum Polymers 0.000 description 1
235000010493 xanthan gum Nutrition 0.000 description 1
229940082509 xanthan gum Drugs 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
239000010457 zeolite Substances 0.000 description 1
239000005943 zeta-Cypermethrin Substances 0.000 description 1

Classifications

- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems

Landscapes

Life Sciences & Earth Sciences (AREA)
Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Dentistry (AREA)
Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Plant Pathology (AREA)
General Health & Medical Sciences (AREA)
Wood Science & Technology (AREA)
Zoology (AREA)
Environmental Sciences (AREA)
Pest Control & Pesticides (AREA)
Agronomy & Crop Science (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)

JP2009186570A 2008-08-13 2009-08-11 ピリジル−トリアゾロピリミジン誘導体又はその塩、並びにそれらを含有する有害生物防除剤 Pending JP2010065026A (ja)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
JP2009186570A JP2010065026A (ja)	2008-08-13	2009-08-11	ピリジル−トリアゾロピリミジン誘導体又はその塩、並びにそれらを含有する有害生物防除剤

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
JP2008208708		2008-08-13
JP2009186570A JP2010065026A (ja)	2008-08-13	2009-08-11	ピリジル−トリアゾロピリミジン誘導体又はその塩、並びにそれらを含有する有害生物防除剤

Publications (1)

Publication Number	Publication Date
JP2010065026A true JP2010065026A (ja)	2010-03-25

Family

ID=41668995

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP2009186570A Pending JP2010065026A (ja)	2008-08-13	2009-08-11	ピリジル−トリアゾロピリミジン誘導体又はその塩、並びにそれらを含有する有害生物防除剤

Country Status (2)

Country	Link
JP (1)	JP2010065026A (fr)
WO (1)	WO2010018853A1 (fr)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CN106905231A (zh) *	2015-12-23	2017-06-30	联化科技股份有限公司	3-氯-5-三氟甲基吡啶类化合物及中间体的制备方法
JP2023513939A (ja) *	2020-02-18	2023-04-04	ピーアイインダストリーズリミテッド	縮合複素環化合物とその害虫防除剤としての利用

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* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB201504565D0 (en)	2015-03-18	2015-05-06	Takeda Pharmaceutical	Novel compounds

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Publication number	Priority date	Publication date	Assignee	Title
JPS4835456B1 (fr) *	1970-12-28	1973-10-27
CN1114606C (zh) *	1998-02-11	2003-07-16	美国氰胺公司	具有杀真菌活性的7－烷基－三唑并嘧啶化合物
JP2002308879A (ja) *	2001-04-13	2002-10-23	Nippon Soda Co Ltd	５−ハロアルキル−アゾロピリミジン化合物、製造方法及び有害生物防除剤
WO2004082383A1 (fr) *	2003-03-17	2004-09-30	Basf Aktiengesellschaft	Utilisation de triazolopyrimidines pour combattre les nematodoses de vegetaux
WO2006092428A2 (fr) *	2005-03-02	2006-09-08	Basf Aktiengesellschaft	7-amino-azolopyrimidine 2-substituee, son procede de fabrication et son utilisation pour lutter contre les champignons nuisibles, et agents renfermant ce compose
JP5231829B2 (ja) *	2007-02-15	2013-07-10	石原産業株式会社	ピリジル−トリアゾロピリミジン誘導体又はその塩、それらを含有する有害生物防除剤並びにそれらの製造方法

2009
- 2009-08-11 JP JP2009186570A patent/JP2010065026A/ja active Pending
- 2009-08-12 WO PCT/JP2009/064275 patent/WO2010018853A1/fr not_active Ceased

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CN106905231A (zh) *	2015-12-23	2017-06-30	联化科技股份有限公司	3-氯-5-三氟甲基吡啶类化合物及中间体的制备方法
JP2023513939A (ja) *	2020-02-18	2023-04-04	ピーアイインダストリーズリミテッド	縮合複素環化合物とその害虫防除剤としての利用
JP7710455B2 (ja)	2020-02-18	2025-07-18	ピーアイインダストリーズリミテッド	縮合複素環化合物、組成物、組み合わせ品、方法、使用、及び種子

Also Published As

Publication number	Publication date
WO2010018853A1 (fr)	2010-02-18

Publication	Publication Date	Title
JP5231829B2 (ja)	2013-07-10	ピリジル−トリアゾロピリミジン誘導体又はその塩、それらを含有する有害生物防除剤並びにそれらの製造方法
JP2010065024A (ja)	2010-03-25	トリアゾロピリミジン誘導体又はその塩を含有する有害生物防除剤
KR20090018657A (ko)	2009-02-20	신규 피리딜-메탄아민 유도체 또는 그의 염을 함유하는 유해 생물 방제제
JP2009029787A (ja)	2009-02-12	Ｎ−フェニル−メタナミン誘導体及びこれを含有する有害生物防除剤
JP2011168582A (ja)	2011-09-01	トリアゾロピリジン誘導体又はその塩、それらの製造方法及びそれらを含有する有害生物防除剤
JP2011144169A (ja)	2011-07-28	イミダゾピリミジン誘導体又はその塩、並びにそれらを含有する有害生物防除剤
JP2010138166A (ja)	2010-06-24	新規ピリジン誘導体又はその塩、それらを含有する有害生物防除剤並びにそれらの製造方法
JP2012087116A (ja)	2012-05-10	ベンズアミド誘導体又はその塩、それらを含有する殺虫剤、殺ダニ剤、殺線虫剤又は殺土壌害虫剤
JP2011105700A (ja)	2011-06-02	ジアリールトリアゾール誘導体又はその塩、それらを含有する殺虫剤、殺ダニ剤、殺線虫剤又は殺土壌害虫剤、並びにそれらの製造方法
JP2010065026A (ja)	2010-03-25	ピリジル−トリアゾロピリミジン誘導体又はその塩、並びにそれらを含有する有害生物防除剤
WO2016068301A1 (fr)	2016-05-06	Agent de lutte contre les parasites
JP2016050201A (ja)	2016-04-11	有害生物防除剤
JP2010195771A (ja)	2010-09-09	トリアゾロピリミジン誘導体又はその塩、それらの製造方法及びそれらを含有する有害生物防除剤
JP2016020335A (ja)	2016-02-04	有害生物防除剤
AU2013364857B2 (en)	2017-02-02	Pest control agent
JP2006001914A (ja)	2006-01-05	ピリミジン系化合物、それらの製造方法及びそれらを含有する有害生物防除剤
WO2017159618A1 (fr)	2017-09-21	Agent de lutte contre les animaux nuisibles
JP2008024697A (ja)	2008-02-07	新規なピリジル−メタナミン誘導体又はその塩を含有する有害生物防除剤
JP2008019222A (ja)	2008-01-31	アントラニルアミド系化合物、それらの製造方法及びそれらを含有する有害生物防除剤
JP2007277206A (ja)	2007-10-25	アントラニルアミド系化合物、それらの製造方法及びそれらを含有する有害生物防除剤
JP2016014016A (ja)	2016-01-28	有害生物防除剤
JP2016011294A (ja)	2016-01-21	有害生物防除剤
JP2007051105A (ja)	2007-03-01	ジフルオロアルカンアミド系化合物、それらの製造方法及びそれらを含有する有害生物防除剤