SI9620006B - Novel carboxylic ester derivatives, the preparation procedure, insecticides and insect repellents containing these derivatives - Google Patents

Novel carboxylic ester derivatives, the preparation procedure, insecticides and insect repellents containing these derivatives Download PDF

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Publication number
SI9620006B
SI9620006B SI9620006A SI9620006A SI9620006B SI 9620006 B SI9620006 B SI 9620006B SI 9620006 A SI9620006 A SI 9620006A SI 9620006 A SI9620006 A SI 9620006A SI 9620006 B SI9620006 B SI 9620006B
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SI
Slovenia
Prior art keywords
group
general formula
hydrogen atom
insecticides
derivatives
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SI9620006A
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English (en)
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SI9620006A (en
Inventor
Yoshio Katsuda
Koji Nakayama
Yoshihiro Minamite
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Dainippon Jochugiku Kk
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Publication of SI9620006A publication Critical patent/SI9620006A/sl
Publication of SI9620006B publication Critical patent/SI9620006B/sl

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D307/40—Radicals substituted by oxygen atoms
    • C07D307/42—Singly bound oxygen 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
    • A01N53/00—Biocides, pest repellants or attractants, or plant growth regulators containing cyclopropane carboxylic acids or derivatives thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/74—Esters of carboxylic acids having an esterified carboxyl group bound to a carbon atom of a ring other than a six-membered aromatic ring
    • C07C69/743—Esters of carboxylic acids having an esterified carboxyl group bound to a carbon atom of a ring other than a six-membered aromatic ring of acids with a three-membered ring and with unsaturation outside the ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
    • C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
    • C07D317/50—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to atoms of the carbocyclic ring
    • C07D317/54—Radicals substituted by oxygen atoms

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Agronomy & Crop Science (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Claims (10)

  1. 0) 1 Patentni zahtevki 1. Derivat estrov karboksilnih kislin s splošno formulo I:
    COO-R2 % označen s tem, da Rj pomeni alkilno skupino z ravno ali razvejeno verigo z 1 do 4 atomi ogljika in R2 pomeni skupino, ki ima naslednjo splošno formulo IV:
    kjer R4 pomeni atom vodika ali etinilno skupino R5 in R^ sta enako ali različno izbrana iz skupine, ki jo sestavljata vodik in metilna skupina R7 je atom vodika in R8 je izbran iz skupine, ki jo sestavljajo propargilna, metoksimetilna in metiltio skupina.
  2. 2. Derivat estrov karboksilnih kislin po zahtevku 1, označen s tem, da ima del ciklopropankarboksilne kisline IR, cis strukturo in ima dvojna vez sterično strukturo Z konfiguracije. 2
  3. 3. Derivat estrov karboksilnih kislin po zahtevku 1 ali 2, označen s tem, da ima naslednjo formulo VIII: (VIH)
    ch2-c=ch.
  4. 4. Derivat estrov karboksilnih kislin po zahtevku 1 ali 2, označen s tem, da ima naslednjo formulo IX:
  5. 5. Derivat estrov karboksilnih kislin po zahtevku 1 ali 2, označen s tem, da ima naslednjo formulo X: CHjCHj HjC-O-C coo—CII2 -tv cii2-o- (X) -cn3.
  6. 6. Insekticidni sestavek, označen s tem, da obsega nosilec in derivat estrov karboksilnih kislin s splošno formulo I: V 3 Η, ch3 ch3 CD >—c / C=CH 'C 00-Ri II o kjer Ri pomeni alkilno skupino z ravno ali razvejeno verigo z 1 do 4 atomi ogljika in R.2 pomeni skupino z naslednjo splošno formulo IV:
    kjer R4 pomeni atom vodika ali etinilno skupino R5 in R^ sta enako ali različno izbrana iz skupine, ki jo sestavljata vodik in metilna skupina R7 je atom vodika in Rg je izbran iz skupine, ki jo sestavljajo propargilna, metoksimetilna in metiltio skupina, atom vodika.
  7. 7. Insekticidni sestavek po zahtevku 6, označen s tem, da obsega spojino, v kateri ima del ciklopropankarboksilne kisline IR, cis strukturo in ima dvojna vez sterično strukturo Z-konfiguracije.
  8. 8. Insekticidni sestavek po zahtevku 6 ali 7, označen s tem, da obsega spojino s splošno formulo VIII: 4 ch3ch3 (Vin) h3c-o—c II o H>=chJ\ •coo-ch2
    ch2-c=ch.
  9. 9. Insekticidni sestavek po zahtevku 6 ali 7, označen s tem, da obsega spojino s splošno formulo IX:
  10. 10. Insekticidni sestavek po zahtevku 6 ali 7, označen s tem, da obsega spojino s splošno formulo X: H h3c~o—c II o / ch^ch3 ^CHv^^coo~ai2^~^--cH2~o~cH3·
SI9620006A 1995-02-07 1996-02-07 Novel carboxylic ester derivatives, the preparation procedure, insecticides and insect repellents containing these derivatives SI9620006B (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP5493695 1995-02-07
PCT/JP1996/000254 WO1996024573A1 (fr) 1995-02-07 1996-02-07 Nouveaux derives d'esters carboxyliques, leurs procedes de production, et insecticide ou insectifuge les contenant

Publications (2)

Publication Number Publication Date
SI9620006A SI9620006A (en) 1997-04-30
SI9620006B true SI9620006B (en) 2001-12-31

Family

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Family Applications (1)

Application Number Title Priority Date Filing Date
SI9620006A SI9620006B (en) 1995-02-07 1996-02-07 Novel carboxylic ester derivatives, the preparation procedure, insecticides and insect repellents containing these derivatives

Country Status (24)

Country Link
US (1) US6107339A (sl)
EP (1) EP0754674B1 (sl)
JP (1) JP3376395B2 (sl)
CN (1) CN1138752C (sl)
AT (1) ATE211127T1 (sl)
AU (1) AU692992B2 (sl)
BG (1) BG63199B1 (sl)
BR (1) BR9605109A (sl)
CA (1) CA2187277C (sl)
CZ (1) CZ290887B6 (sl)
DE (1) DE69618096T2 (sl)
FI (1) FI963943A (sl)
HU (1) HU216081B (sl)
MY (1) MY114703A (sl)
NO (1) NO306942B1 (sl)
OA (1) OA10590A (sl)
PL (1) PL182472B1 (sl)
RO (1) RO118424B1 (sl)
RU (1) RU2168492C2 (sl)
SI (1) SI9620006B (sl)
SK (1) SK284829B6 (sl)
TW (1) TW342384B (sl)
UA (1) UA57591C2 (sl)
WO (1) WO1996024573A1 (sl)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP4474745B2 (ja) * 1999-12-10 2010-06-09 住友化学株式会社 エステル化合物、その用途およびその製造中間体
KR20040041660A (ko) * 2001-10-03 2004-05-17 다이니혼 죠츄기쿠 가부시키가이샤 프로파길 벤질 알코올 에스테르 유도체, 그 제조방법, 및이것을 함유하는 살충·방충제
DE10320505A1 (de) * 2003-05-08 2004-11-25 Bayer Healthcare Ag Mittel zum Bekämpfen von Parasiten an Tieren
KR101125360B1 (ko) * 2003-11-26 2012-03-27 스미또모 가가꾸 가부시키가이샤 카르복실산 에스테르의 제조 방법
CN102020564A (zh) * 2009-09-17 2011-04-20 上海生农生化制品有限公司 一种带炔键的含氟环丙烷羧酸酯及其制备方法和用途

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US2458656A (en) * 1946-03-26 1949-01-11 Thompson Boyce Plant Res Esters of piperonyl chrysanthemum carboxylic acid
US2886485A (en) * 1957-09-12 1959-05-12 William F Barthel 6-bromopiperonyl and 6-chloropiperonyl esters of chrysanthemumic acid as insecticides
DE1793312A1 (de) * 1968-08-29 1971-07-08 Basf Ag Substituierte Chrysanthemumsaeureester und diese enthaltende Schaedlingsbekaempfungsmittel
JPS49489B1 (sl) * 1970-06-13 1974-01-08
US4024163A (en) * 1972-05-25 1977-05-17 National Research Development Corporation Insecticides
DE3065914D1 (en) * 1979-12-21 1984-01-19 Ici Plc Substituted benzyl esters of cyclopropane carboxylic acids and their preparation, compositions containing them and methods of combating insect pests therewith, and substituted benzyl alcohols
US4370346A (en) * 1979-12-21 1983-01-25 Imperial Chemical Industries Plc Halogenated esters
FR2482955A1 (fr) * 1980-05-23 1981-11-27 Roussel Uclaf Nouveaux derives de l'acide cyclopropane carboxylique, leur procede de preparation et leur application a la lutte contre les parasites
FR2536392A2 (fr) * 1982-11-22 1984-05-25 Roussel Uclaf Nouveaux derives de l'acide cyclopropane carboxylique, leur procede de preparation et leur application a la lutte contre les parasites
US4489093A (en) * 1980-10-01 1984-12-18 Roussel Uclaf Insecticidal esters
FR2526422B1 (fr) * 1982-05-06 1985-09-20 Roussel Uclaf Nouveau procede de preparation de derives de l'acide cyclopropane carboxylique
US4542142A (en) * 1982-11-22 1985-09-17 Roussel Uclaf Insecticidal cyclopropane carboxylic acid derivatives with 3-unsaturated-side chain
FR2536748A1 (fr) * 1982-11-25 1984-06-01 Roussel Uclaf Nouveaux esters derives d'acides 2,2-dimethyl cyclopropane carboxyliques et d'alcools biaryliques, leur procede de preparation et leur application a la lutte contre les parasites
FR2539411B2 (fr) * 1983-01-17 1986-04-25 Roussel Uclaf Nouveaux derives de l'acide cyclopropane carboxylique, leur procede de preparation, leur application a la lutte contre les parasites
FR2610624B1 (fr) * 1987-02-06 1989-06-09 Roussel Uclaf Nouveaux esters d'acides cyclopropanecarboxyliques apparentes a l'acide pyrethrique, leur procede de preparation et leur application a la lutte contre les parasites
JPS63267706A (ja) * 1987-04-22 1988-11-04 Dainippon Jiyochiyuugiku Kk ベンジルアルコ−ルエステルを含有する燻焼用及び加熱蒸散用殺虫剤ならびにその製造法
JP2570388B2 (ja) * 1988-06-10 1997-01-08 住友化学工業株式会社 カルボン酸エステルおよびその殺虫剤としての用途
FR2687152A1 (fr) * 1992-02-07 1993-08-13 Roussel Uclaf Nouveaux esters pyrethrinouides derives d'alcool furanique ou thiophenique, leur procede de preparation et leur application comme pesticides.
FR2687666A1 (fr) * 1992-02-21 1993-08-27 Roussel Uclaf Nouveaux esters pyrethrinouiques, derives de l'alcool 6-(trifluoromethyl) benzylique, leur procede de preparation et leur application comme pesticides.
JP3063871B2 (ja) * 1992-03-30 2000-07-12 大日本除蟲菊株式会社 置換ベンジルアルコールエステル誘導体を含有する殺虫 、防虫、忌避剤、ならびにこれを用いた殺虫、防虫、忌 避方法。
FR2691966A1 (fr) * 1992-06-04 1993-12-03 Roussel Uclaf Nouveau procédé de préparation d'esters de l'acide 2,2-diméthyl 3-[(z) 1-propényl] cyclopropane carboxylique et intermédiaires.
JPH07112947A (ja) * 1993-08-24 1995-05-02 Sumitomo Chem Co Ltd エステル化合物、それを有効成分とする有害生物防除剤、その製造中間体およびその製造法

Also Published As

Publication number Publication date
HUP9603080A2 (en) 1997-05-28
BG100966A (en) 1998-03-31
EP0754674A4 (en) 1998-07-08
CZ325996A3 (en) 1997-04-16
CN1148379A (zh) 1997-04-23
FI963943A0 (fi) 1996-10-02
CZ290887B6 (cs) 2002-11-13
HUP9603080A3 (en) 1997-08-28
US6107339A (en) 2000-08-22
BR9605109A (pt) 1997-10-07
CN1138752C (zh) 2004-02-18
AU4632596A (en) 1996-08-27
JP3376395B2 (ja) 2003-02-10
PL316872A1 (en) 1997-02-17
EP0754674A1 (en) 1997-01-22
SK139796A3 (en) 1997-04-09
HU216081B (hu) 1999-04-28
MY114703A (en) 2002-12-31
DE69618096T2 (de) 2002-07-18
RU2168492C2 (ru) 2001-06-10
BG63199B1 (bg) 2001-06-29
ATE211127T1 (de) 2002-01-15
NO964219D0 (no) 1996-10-04
DE69618096D1 (de) 2002-01-31
CA2187277A1 (en) 1996-08-15
AU692992B2 (en) 1998-06-18
SK284829B6 (sk) 2005-12-01
EP0754674B1 (en) 2001-12-19
FI963943A (fi) 1996-10-16
WO1996024573A1 (fr) 1996-08-15
RO118424B1 (ro) 2003-05-30
TW342384B (en) 1998-10-11
OA10590A (en) 2002-07-15
CA2187277C (en) 2002-04-30
PL182472B1 (pl) 2002-01-31
NO306942B1 (no) 2000-01-17
SI9620006A (en) 1997-04-30
UA57591C2 (uk) 2003-06-16
NO964219L (no) 1996-11-07

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