JP2001504840A - 有害生物防除剤としての3−チオカルバモイルピラゾール誘導体 - Google Patents
有害生物防除剤としての3−チオカルバモイルピラゾール誘導体Info
- Publication number
- JP2001504840A JP2001504840A JP52513298A JP52513298A JP2001504840A JP 2001504840 A JP2001504840 A JP 2001504840A JP 52513298 A JP52513298 A JP 52513298A JP 52513298 A JP52513298 A JP 52513298A JP 2001504840 A JP2001504840 A JP 2001504840A
- Authority
- JP
- Japan
- Prior art keywords
- spp
- formula
- compound
- active compound
- same
- Prior art date
- 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.)
- Granted
Links
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- 125000001424 substituent group Chemical group 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
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- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 239000003921 oil Substances 0.000 description 6
- 235000019198 oils Nutrition 0.000 description 6
- 239000003960 organic solvent Substances 0.000 description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 5
- 235000011303 Brassica alboglabra Nutrition 0.000 description 5
- 235000011302 Brassica oleracea Nutrition 0.000 description 5
- 235000003899 Brassica oleracea var acephala Nutrition 0.000 description 5
- 235000011301 Brassica oleracea var capitata Nutrition 0.000 description 5
- 235000001169 Brassica oleracea var oleracea Nutrition 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 5
- 241000196324 Embryophyta Species 0.000 description 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 5
- 125000001931 aliphatic group Chemical group 0.000 description 5
- 229920000180 alkyd Polymers 0.000 description 5
- 238000001035 drying Methods 0.000 description 5
- 150000002148 esters Chemical class 0.000 description 5
- 150000002430 hydrocarbons Chemical group 0.000 description 5
- 150000002576 ketones Chemical class 0.000 description 5
- 239000000123 paper Substances 0.000 description 5
- 238000003359 percent control normalization Methods 0.000 description 5
- 239000003208 petroleum Substances 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 229910052717 sulfur Inorganic materials 0.000 description 5
- 239000011593 sulfur Substances 0.000 description 5
- 238000012546 transfer Methods 0.000 description 5
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 5
- 239000002023 wood Substances 0.000 description 5
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 4
- WNZQDUSMALZDQF-UHFFFAOYSA-N 2-benzofuran-1(3H)-one Chemical compound C1=CC=C2C(=O)OCC2=C1 WNZQDUSMALZDQF-UHFFFAOYSA-N 0.000 description 4
- 241000239290 Araneae Species 0.000 description 4
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- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 4
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- 241000238680 Rhipicephalus microplus Species 0.000 description 4
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- 239000002253 acid Substances 0.000 description 4
- 125000003545 alkoxy group Chemical group 0.000 description 4
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- LESVOLZBIFDZGS-UHFFFAOYSA-N vamidothion Chemical compound CNC(=O)C(C)SCCSP(=O)(OC)OC LESVOLZBIFDZGS-UHFFFAOYSA-N 0.000 description 1
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- WCJYTPVNMWIZCG-UHFFFAOYSA-N xylylcarb Chemical compound CNC(=O)OC1=CC=C(C)C(C)=C1 WCJYTPVNMWIZCG-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 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
- JLYXXMFPNIAWKQ-UHFFFAOYSA-N γ Benzene hexachloride Chemical compound ClC1C(Cl)C(Cl)C(Cl)C(Cl)C1Cl JLYXXMFPNIAWKQ-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D231/38—Nitrogen atoms
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/32—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D207/325—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms with substituted hydrocarbon radicals directly attached to the ring nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D231/18—One oxygen or sulfur atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D231/44—Oxygen and nitrogen or sulfur and nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Description
Claims (1)
- 【特許請求の範囲】 1. 一般式(I) [式中、R1は、H2N−CS−を表し、 R2は、ハロゲノアルキル、ハロゲノアルケニル又はハロゲノアルキニルを 表し、 R3は、水素、アミノ;又は下記の基: {ここで、R4は、アルキル、ハロゲノアルキル、アルコキシアルキル;又 はそれぞれの場合に場合により置換されたフェニル又はピリジルを表し、 R5は、水素又はアルキルを表し、 R6は、水素、アルキル;又はそれぞれの場合に場合により置換されたフェ ニル又はピリジルを表し、並びに R7は、アルキル、アルケニル、アルキニル、ホルミル、アルキルカルボニ ル、ハロゲノアルキルカルボニル又はアルコキシカルボニルを表す。} の中の1つを表し、 Arは、それぞれの場合に場合により置換されたフェニル又はピ リジルを表し、並びに nは、数字0、1又は2を表す。] の化合物。 2.a)式(II) [式中、Ar、R2、R3及びnは請求の範囲1において定義したと同じで ある。] の3−シアノピラゾール誘導体を、適切であれば反応助剤の存在下、また、適切 であれば希釈剤の存在下で、硫化水素と反応させるか;又は b)式(III) [式中、Arは、上で定義したと同じであり、並びに R3-1は、下記の基: (ここで、R4、R5、R6及びR7は、上で定義したと同じである。) の中の1つを表す。] の3−チオカルバモイルピラゾール誘導体を、適切であれば希釈剤の存在下、ま た、適切であれば反応助剤の存在下で、式(IV) Hal−S−R2 (IV) [式中、R2は上で定義したと同じであり、並びに Halはハロゲンを表す。] のスルフェニルハライド類と反応させるか;又は c)式(Ia) [式中、Ar、R2及びR3は上で定義したと同じであり、また、方法(a )もしくは(b)によって得ることができる。] の2−チオカルバモイルピラゾール誘導体を、適切であれば希釈剤の存在下、ま た、適切であれば触媒の存在下で、酸化体で酸化することを特徴とする、請求の 範囲1に記載の式(I)の化合物の製造方法。 3. 式(III) [式中、Arは上で定義したと同じであり、並びに R3-1は、下記の基: (ここで、R4、R5、R6及びR7は請求項1において定義したと同じであ る。) の中の1つを表す。] の化合物。 4. 式(VII) [式中、Arは上で定義したと同じである。] の化合物。 5. 請求項1に記載の式(I)の少なくとも1つの化合物を含むことを特徴 とする有害生物防除剤。 6. 有害生物を防除するための、請求の範囲1に記載の式(I)の化合物の 使用。 7. 請求の範囲1に記載の式(I)の化合物を、有害生物及び/又はそれら の環境に作用させることを特徴とする、有害生物の防除方法。 8. 請求の範囲1に記載の式(I)の化合物を増量剤及び/又は界面活性剤 と混合することを特徴とする、有害生物防除剤の製造方法。 9. 有害生物防除剤を製造するための、請求の範囲1に記載の式(I)の化 合物の使用。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
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DE19650197A DE19650197A1 (de) | 1996-12-04 | 1996-12-04 | 3-Thiocarbamoylpyrazol-Derivate |
DE19650197.0 | 1996-12-04 | ||
PCT/EP1997/006503 WO1998024769A1 (de) | 1996-12-04 | 1997-11-21 | 3-thiocarbamoylpyrazol-derivate als pestiziden |
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JP2001504840A true JP2001504840A (ja) | 2001-04-10 |
JP4434317B2 JP4434317B2 (ja) | 2010-03-17 |
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JP52513298A Expired - Fee Related JP4434317B2 (ja) | 1996-12-04 | 1997-11-21 | 有害生物防除剤としての3−チオカルバモイルピラゾール誘導体 |
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US (1) | US6265430B1 (ja) |
EP (1) | EP0942904B1 (ja) |
JP (1) | JP4434317B2 (ja) |
KR (1) | KR100512842B1 (ja) |
CN (1) | CN1105709C (ja) |
AT (1) | ATE269850T1 (ja) |
AU (1) | AU726611B2 (ja) |
BR (1) | BR9714377B1 (ja) |
CA (1) | CA2273841C (ja) |
DE (2) | DE19650197A1 (ja) |
ES (1) | ES2224285T3 (ja) |
HK (1) | HK1024480A1 (ja) |
HU (1) | HUP0000369A3 (ja) |
IL (1) | IL130260A (ja) |
NZ (1) | NZ336057A (ja) |
PL (1) | PL191739B1 (ja) |
PT (1) | PT942904E (ja) |
TR (1) | TR199901238T2 (ja) |
WO (1) | WO1998024769A1 (ja) |
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1997
- 1997-11-21 JP JP52513298A patent/JP4434317B2/ja not_active Expired - Fee Related
- 1997-11-21 BR BRPI9714377-4A patent/BR9714377B1/pt not_active IP Right Cessation
- 1997-11-21 TR TR1999/01238T patent/TR199901238T2/xx unknown
- 1997-11-21 PL PL333533A patent/PL191739B1/pl not_active IP Right Cessation
- 1997-11-21 AT AT97951934T patent/ATE269850T1/de not_active IP Right Cessation
- 1997-11-21 EP EP97951934A patent/EP0942904B1/de not_active Expired - Lifetime
- 1997-11-21 HU HU0000369A patent/HUP0000369A3/hu unknown
- 1997-11-21 WO PCT/EP1997/006503 patent/WO1998024769A1/de active IP Right Grant
- 1997-11-21 CN CN97180290A patent/CN1105709C/zh not_active Expired - Fee Related
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- 1997-11-21 KR KR10-1999-7004894A patent/KR100512842B1/ko not_active IP Right Cessation
- 1997-11-21 ES ES97951934T patent/ES2224285T3/es not_active Expired - Lifetime
- 1997-11-21 PT PT97951934T patent/PT942904E/pt unknown
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Cited By (3)
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JP2007529439A (ja) * | 2004-03-15 | 2007-10-25 | バイエル・クロツプサイエンス・エス・アー | 1−フェニル及び1−ピリジルピラゾール誘導体及びその殺虫剤としての使用 |
JP2007532683A (ja) * | 2004-04-16 | 2007-11-15 | メリアル リミテッド | 動物の外部寄生虫を治療、予防及び抑制するための、抗寄生虫薬及び方法 |
JP2008519777A (ja) * | 2004-11-11 | 2008-06-12 | バイエルクロップサイエンス エス.エイ. | 有害生物防除剤としてのビニルアミノピラゾール誘導体 |
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BR9714377A (pt) | 2000-03-21 |
EP0942904A1 (de) | 1999-09-22 |
CN1105709C (zh) | 2003-04-16 |
DE59711733D1 (de) | 2004-07-29 |
EP0942904B1 (de) | 2004-06-23 |
PT942904E (pt) | 2004-11-30 |
PL191739B1 (pl) | 2006-06-30 |
JP4434317B2 (ja) | 2010-03-17 |
CN1239953A (zh) | 1999-12-29 |
ATE269850T1 (de) | 2004-07-15 |
TR199901238T2 (xx) | 1999-08-23 |
AU5554198A (en) | 1998-06-29 |
HUP0000369A2 (hu) | 2000-06-28 |
IL130260A (en) | 2003-07-06 |
BR9714377B1 (pt) | 2008-11-18 |
US6265430B1 (en) | 2001-07-24 |
AU726611B2 (en) | 2000-11-16 |
CA2273841C (en) | 2007-04-10 |
CA2273841A1 (en) | 1998-06-11 |
DE19650197A1 (de) | 1998-06-10 |
WO1998024769A1 (de) | 1998-06-11 |
HK1024480A1 (en) | 2000-10-13 |
NZ336057A (en) | 2001-03-30 |
ES2224285T3 (es) | 2005-03-01 |
KR100512842B1 (ko) | 2005-09-07 |
KR20000069272A (ko) | 2000-11-25 |
IL130260A0 (en) | 2000-06-01 |
US20010007876A1 (en) | 2001-07-12 |
HUP0000369A3 (en) | 2002-01-28 |
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