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US4097592A
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O- 1-substituted-6-pyridazinon(3)yl!-thionoalkanephosphonic acid esters for combating insects and acarids
Assignee: Bayer AG
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Filing: 1976-07-26
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Granted: 1978-06-27
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Expires: 1996-07-26
Abstract
Abstract O- 1-substituted-6-pyridazinon(3)yl!-thionoalkanephosphonic acid esters of the formula ##STR1## in which R 1 and R 2 each independently is alkyl with 1 to 7 carbon atoms, R 3 is alkyl, cyanoalkyl, alkylcarbonylalkyl, carbalkoxyalkyl, hydroxyalkyl, alkylthioalkyl or halogenalkyl with 1 to 4 carbon atoms per alkyl radical, alkenyl or alkynyl with 3 to 5 carbon atoms, benzyl, benzyl carrying at least one substituent selected from halogen and alkyl with 1 to 3 carbon atoms, phenyl, phenyl carrying at least one substituent selected from nitro, halogen, alkyl with 1 to 3 carbon atoms and carbalkoxy with 1 to 4 carbon atoms, morpholinomethyl or piperidinomethyl, R 4 and R 5 each independently is hydrogen or alkyl with 1 to 3 carbon atoms, and X and Y each independently is oxygen or sulfur, Which possess insecticidal and acaricidal properties.
Inventors
- 👤 Wolfgang Hofer
- 👤 Fritz Maurer
- 👤 Hans-Jochem Riebel
- 👤 Lothar Rohe
- 👤 Rolf Schroder
- 👤 Ingeborg Hammann
- 👤 Wolfgang Behrenz
- 👤 Bernhard Homeyer
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-07 13:10
CPC Classifications
A; A01; A01N; A01N57/00; A01N57/18; A01N57/24; C; C07; C07F; C07F9/00; C07F9/02; C07F9/547; C07F9/645; C07F9/6509; C07F9/650905
Claims Analysis
Total Claims: 11
Claim 1
Independent Claim
129 words
An O- 1-substituted-6-pyridazinon(3)yl!(thiono)(thiol)-alkanephosphonic acid ester of the formula ##STR300## in which R 1 and R 2 each independently is alkyl with 1 to 7 carbon atoms, R 3 is alkyl, cyanoalkyl, alkylcarbonylalkyl, carbalkoxyalkyl, hydroxyalkyl, alkylthioalkyl or halogenoalkyl with 1 to 4 carbon atoms per alkyl radical, alkenyl or alkenyl with 3 to 5 carbon atoms, benzyl, benzyl carrying at least one substituent selected from halogen and alkyl with 1 to 3 carbon atoms, or phenyl, phenyl carrying at least one substituent selected from nitro, halogen, alkyl with 1 to 3 carbon atoms and carbalkoxy with 1 to 4 carbon atoms, or piperidinomethyl, R 4 and R 5 each independently is hydrogen or alkyl with 1 to 3 carbon atoms, and X and Y each independently is oxygen or sulfur.
Claim 2
Dependent Claim
129 words
An O- 1-substituted-6-pyridazinon(3)yl!(thiono)(thiol)-alkanephosphonic acid ester of the formula ##STR300## in which R 1 and R 2 each independently is alkyl with 1 to 7 carbon atoms, R 3 is alkyl, cyanoalkyl, alkylcarbonylalkyl, carbalkoxyalkyl, hydroxyalkyl, alkylthioalkyl or halogenoalkyl with 1 to 4 carbon atoms per alkyl radical, alkenyl or alkenyl with 3 to 5 carbon atoms, benzyl, benzyl carrying at least one substituent selected from halogen and alkyl with 1 to 3 carbon atoms, or phenyl, phenyl carrying at least one substituent selected from nitro, halogen, alkyl with 1 to 3 carbon atoms and carbalkoxy with 1 to 4 carbon atoms, or piperidinomethyl, R 4 and R 5 each independently is hydrogen or alkyl with 1 to 3 carbon atoms, and X and Y each independently is oxygen or sulfur.
Claim 3
Dependent Claim
102 words
An ester according to claim 1, in which X is sulfur, Y is oxygen, R 1 is alkyl with 1 to 5 carbon atoms, R 2 is alkyl with 1 to 3 carbon atoms, R 4 and R 5 each independently is hydrogen or methyl, and R 3 is alkenyl or alkynyl with 3 or 4 carbon atoms, hydroxyalkyl, cyanoalkyl, alkylthioalkyl, chloroalkyl, methylcarbonylalkyl, ethylcarbonylalkyl, carbalkoxyalkyl or alkyl, each with 1 to 3 carbon atoms per alkyl radical, benzyl chlorobenzyl, methylbenzyl, phenyl, phenyl substituted by nitro, chlorine, methyl, ethyl or carbalkoxy with 1 to 3 carbon atoms in the alkoxy radical, or piperidinomethyl.
Claim 4
Dependent Claim
17 words
An ester according to claim 1 wherein such ester is O-methyl-O- 1-methyl-6-pyridazinon(3)yl!-thionoethanephosphonic acid of the formula ##STR301##
Claim 5
Dependent Claim
18 words
An ester according to claim 1 wherein such ester is O-ethyl-O- 1-phenyl-6-pyridazinon(3)yl!-thionoethanephosphonic acid ester of the formula ##STR302##
Claim 6
Dependent Claim
18 words
An ester according to claim 1 wherein such ester is O-n-propyl-O- 1-phenyl-6-pyridazinon(3)yl!-thionoethanephosphonic acid ester of the formula ##STR303##
Claim 7
Dependent Claim
18 words
An ester according to claim 1 wherein such ester is O-ethyl-O- 1-β-chloroethyl-6-pyridazinon(3)yl!-thionoethanephosphonic acid ester of the formula ##STR304##
Claim 8
Dependent Claim
18 words
An ester according to claim 1 wherein such ester is O-ethyl-O- 1-allyl-6-pyridazinon(3)yl!-thionoethanephosphonic acid ester of the formula ##STR305##
Claim 9
Dependent Claim
25 words
An insecticidal or acaricidal composition containing as active ingredient an insecticidally or acaricidally effective amount of an ester according to claim 1 and a carrier.
Claim 10
Dependent Claim
33 words
A method of combating insects or acarids which comprises applying to the insects or acarids or to a habitat thereof an insecticidally or acaricidally effective amount of an ester according to claim 1.
Claim 11
Dependent Claim
31 words
The method according to claim 9 in which said ester is O-methyl-O- 1-methyl-6-pyridazinon(3)yl!-thionoethanephosphonic acid, O-ethyl-O- 1-phenyl-6-pyridazinon(3)yl!-thionoethanephosphonic acid ester, O-n-propyl-O- 1-phenyl-6-pyridazinon(3)yl!-thionoethanephosphonic acid ester, O-ethyl-O- 1-β-chloroethyl-6-pyridazinon(3)yl!thionoethanephosphonic acid ester, or O-ethyl-O- 1-allyl-6-pyridazinon(3)yl!-thionoethanephosphonic acid ester.
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1981-06-26 | 1981-12-26 | 1982-06-27 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1985-06-26 | 1985-12-26 | 1986-06-27 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1989-06-26 | 1989-12-26 | 1990-06-27 | $7700.00 | Window Closed / Lapsed |