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US4473558A Expired / Lapsed US ⏱️ 0.0 years remaining

2-(Thi)oxo-1,3,2-oxazaphospholanes as synergizing agents for pesticides

Assignee: Bayer AG
•
Filing: 1982-07-26
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Granted: 1984-09-25
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Expires: 2002-07-26
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Abstract

Abstract In a synergistic pesticidal composition comprising (1) a pesticidally active compound and (2) a synergizing agent in amount sufficient to synergize the pesticidal activity of the pesticidally active compound, the improvement which comprises employing as the synergizing agent a 2-(thi)oxo-1,3,2-oxazaphospholane of the formula ##STR1## in which X represents oxygen or sulphur, R represents an optionally substituted alkyl, alkenyl, alkynyl, phenyl, alkoxy, alkenoxy, alkynoxy, alkylthio, aralkoxy, amino, mono- or di-alkylamino, heterocyclic amino, N-alkyl-N-aryl-amino, phenoxy or phenylthio radical, R 1 represents hydrogen, optionally substituted alkyl, aralkyl, alkenyl, alkynyl or dialkylaminoalkyl, R 2 represents hydrogen, alkylthioalkyl, or optionally substituted alkyl or aralkyl, or R 1 and R 2 together represent alkylene, R 3 represents hydrogen or alkyl and R 4 represents hydrogen, alkyl, or phenyl.

Inventors

  • 👤 Hellmut Hoffmann
  • 👤 Bernd-Wieland Kruger
  • 👤 Wolfgang Behrenz

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-24 19:20
CPC Classifications
C; C07; C07F; C07F9/00; C07F9/02; C07F9/547; C07F9/6564; C07F9/6581; C07F9/6584; C07F9/65842; C07F9/65844; A; A01; A01N; A01N57/00; A01N57/36

Claims Analysis

Total Claims: 18
Claim 1
Independent Claim 232 words
In a synergistic insecticidal and acaricidal composition comprising (1) an insecticidally and acaricidally active compound and (2) a synergizing agent in amount sufficient to synergize the insecticidal and acaricidal activity of the insecticidally and acaricidally active compound, the improvement which comprises employing as the synergizing agent a 2-(thi)oxo-1,3,2-oxazaphospholane of the formula ##STR67## in which X represents oxygen or sulphur, R represents optionally halogen-substituted C 1 -C 4 -alkyl, C 2 -C 5 -alkenyl, C 2 -C 5 -alkynyl, phenyl C 1 -C 4 -alkoxy, C 2 -C 5 -alkenoxy, C 2 -C 5 -alkynoxy, C 1 -C 4 -alkylthio, amino, C 1 -C 4 -alkylamino, di-(C 1 -C 4 -alkyl)-amino, dimethylamino-methylene-amino, morpholino, pyrrolidino or piperidino, or a phenoxy or phenylthio radical which optionally carries one or more substituents selected from halogen, optionally halogen-substituted C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 2 -alkylenedioxy or C 1 -C 4 -alkylthio radicals, cyano and nitro, R 1 represents hydrogen, C 1 -C 4 -alkyl, di-(C 1 -C 2 -alkyl)amino, C 1 -C 2 -alkyl or C 2 -C 5 -alkenyl, R 2 represents hydrogen, C 1 -C 4 -alkyl, C 1 -C 4 -alkylthio-C 1 -C 2 -alkyl or benzyl, or R 1 and R 2 together represent propane-1,3-diyl and R 3 represents C 1 -C 3 -alkyl, hydrogen or phenyl, and R 4 represents hydrogen, alkyl, or phenyl,
Claim 2
Dependent Claim 232 words
In a synergistic insecticidal and acaricidal composition comprising (1) an insecticidally and acaricidally active compound and (2) a synergizing agent in amount sufficient to synergize the insecticidal and acaricidal activity of the insecticidally and acaricidally active compound, the improvement which comprises employing as the synergizing agent a 2-(thi)oxo-1,3,2-oxazaphospholane of the formula ##STR67## in which X represents oxygen or sulphur, R represents optionally halogen-substituted C 1 -C 4 -alkyl, C 2 -C 5 -alkenyl, C 2 -C 5 -alkynyl, phenyl C 1 -C 4 -alkoxy, C 2 -C 5 -alkenoxy, C 2 -C 5 -alkynoxy, C 1 -C 4 -alkylthio, amino, C 1 -C 4 -alkylamino, di-(C 1 -C 4 -alkyl)-amino, dimethylamino-methylene-amino, morpholino, pyrrolidino or piperidino, or a phenoxy or phenylthio radical which optionally carries one or more substituents selected from halogen, optionally halogen-substituted C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 2 -alkylenedioxy or C 1 -C 4 -alkylthio radicals, cyano and nitro, R 1 represents hydrogen, C 1 -C 4 -alkyl, di-(C 1 -C 2 -alkyl)amino, C 1 -C 2 -alkyl or C 2 -C 5 -alkenyl, R 2 represents hydrogen, C 1 -C 4 -alkyl, C 1 -C 4 -alkylthio-C 1 -C 2 -alkyl or benzyl, or R 1 and R 2 together represent propane-1,3-diyl and R 3 represents C 1 -C 3 -alkyl, hydrogen or phenyl, and R 4 represents hydrogen, alkyl, or phenyl,
Claim 3
Dependent Claim 10 words
A composition according to claim 1, wherein (2) is ##STR68##
Claim 4
Dependent Claim 39 words
A composition according to claim 1, wherein (1) is selected from (A) carbamic acid esters, (B) carboxylic acid esters, including the naturally occurring and the synthetic pyrethroids, (C) phosphoric acid esters and phosphonic acid esters and (D) halogeno(cyclo) alkanes.
Claim 5
Dependent Claim 331 words
A composition according to claim 1, wherein (1) is selected from (A) carbamic acid esters of the formula ##STR69## in which R 5 represents hydrogen or C 1 -C 4 -alkyl, R 6 represents C 1 -C 4 -alkyl, C 1 -C 4 -alkylcarbonyl which is optionally substituted by halogen, by hydroxyl or by methylthio, or the radical S-Z, Z represents optionally halogen-substituted C 1 -C 4 -alkyl, phenyl which optionally carries one or more substituents selected from halogen, cyano, C 1 -C 4 -alkyl, trihalogenomethylthio, trihalogenomethyl and nitro, or C 1 -C 4 -alkoxy-carbonyl and R 7 represents an optionally substituted aryl, heterocyclic or oxime radical. (B) carboxylic acid esters of the formula ##STR70## in which R 12 represents an open-chain or cyclic alkyl radical which is optionally substituted by halogen, by alkyl, by cycloalkyl, by alkenyl which is optionally substituted by halogen and/or alkoxy, by phenyl or styryl, in either case optionally substituted by halogen or one or more substituents selected from optionally halogen-substituted alkyl, alkoxy, alkylenedioxy and alkylthio radicals, or by cycloalk(en)yl which is linked in a spirocyclic-like manner and is optionally halogen-substituted and optionally benzo-fused, R 10 represents hydrogen, alkyl, halogenoalkyl, alkenyl, alkynyl or cyano and R 11 represents an optionally substituted aryl radical or a heterocyclic radical, or R 10 and R 11 , together with the carbon atom to which the two radicals are bonded, form a cyclopentenone ring, and naturally occurring pyrethroids, (C) phosphoric acid esters and phosphonic acid esters of the formula ##STR71## in which X' represents oxygen or sulphur, Y' represents oxygen, sulphur, imino or a direct bond between the P atom and R 19 , R 17 and R 18 are identical or different and each represents an optionally substituted alkyl or aryl radical and R 19 represents an optionally substituted alkyl, aryl, heteroaryl, aralkyl or alkenyl radical, an optionally substituted oxime radical, or a radical identical to that to which it is bonded, and (D) hexachlorocyclohexane, 1,1,1-trichloro-2,2-bis-(4-chlorophenyl)-ethane, 1,1,1-trichloro-2,2-bis-(4-methoxyphenyl)-ethane and 1,1-dichloro-2,2-bis-(4-ethylphenyl)-ethane.
Claim 6
Dependent Claim 20 words
A composition according to claim 1, wherein the weight ratio of (1) to (2) is from about 0.1:10 to 10:0.1.
Claim 7
Dependent Claim 9 words
A composition according to claim 1, wherein (2) ##STR72##
Claim 8
Dependent Claim 10 words
A composition according to claim 1, wherein (2) is ##STR73##
Claim 9
Dependent Claim 10 words
A composition according to claim 1, wherein (2) is ##STR74##
Claim 10
Dependent Claim 10 words
A composition according to claim 1, wherein (2) is ##STR75##
Claim 11
Dependent Claim 10 words
A composition according to claim 1, wherein (2) is ##STR76##
Claim 12
Dependent Claim 10 words
A composition according to claim 1, wherein (2) is ##STR77##
Claim 13
Dependent Claim 10 words
A composition according to claim 1, wherein (2) is ##STR78##
Claim 14
Dependent Claim 10 words
A composition according to claim 1, wherein (2) is ##STR79##
Claim 15
Dependent Claim 10 words
A composition according to claim 1, wherein (2) is ##STR80##
Claim 16
Dependent Claim 10 words
A composition according to claim 1, wherein (2) is ##STR81##
Claim 17
Dependent Claim 25 words
A method of combating pests comprising applying to the pests or a habitat thereof a pesticidally effective amount of a composition according to claim 1.
Claim 18
Dependent Claim 10 words
A method according to claim 16, wherein (2) is ##STR82##

References Cited (Backward Citations)

US2865948A Cited
US3285999A Cited
DE2810923A1 Cited
US4190651A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1987-09-25 1988-03-26 1988-09-25 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1991-09-25 1992-03-26 1992-09-25 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1995-09-25 1996-03-26 1996-09-25 $7700.00 Window Closed / Lapsed

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