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US4444764A
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Phosphorus esters of alkylcycloalkyl-5-pyrimidinols and control of corn rootworm and western spotted cucumber beetle with them
Assignee: Dow Chemical Co
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Filing: 1981-03-23
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Granted: 1984-04-24
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Expires: 2001-03-23
Abstract
Abstract Compounds of the formulas: ##STR1## wherein R is alkylcycloalkyl having 4 to 6 carbon atoms; R' is hydrogen, alkyl or alkylthio of 1 to 3 carbons; R" is alkyl having 1 to 4 carbon atoms; X is oxygen or sulfur; and R'" is alkyl of 1 to 2 carbons, alkoxy, alkylthio or monoalkylamino, each with 1 to 4 carbon atoms, or phenyl. The novel 1-alkylcycloalkyl pyrimidinols are used in preparing the phosphate compounds which are highly useful corn rootworm control agents and are particularly valuable when applied to the soil, but are also useful applied to foliage of corn. Especially good control is obtained of corn rootworm. The compounds are conveniently applied in the form of a composition containing a pesticidal carrier such as an inert solvent or a finely divided inert solid in which case the composition is preferably granulated. An effective application rate is in the range of about 0.1 to about 5 pounds per acre when soil incorporated, and about 0.5 to about 2000 ppm for foliar applications.
Inventors
- 👤 Walter Reifschneider
- 👤 Larry L. Larson
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-06 20:14
CPC Classifications
C; C07; C07D; C07D239/00; C07D239/02; C07D239/24; C07D239/28; C07D239/32; C07D239/34; C07D239/36; A; A01; A01N; A01N57/00; A01N57/02; A01N57/08; C07D239/46; C07D239/56; C07F; C07F9/00; C07F9/02; C07F9/547; C07F9/645; C07F9/6509; C07F9/6512
Claims Analysis
Total Claims: 22
Claim 1
Independent Claim
34 words
A compound having the formula: ##STR12## wherein R" is alkyl having 1 to 4 carbon atoms and R"' is alkyl of 1 to 2 carbons, alkoxy having 1 to 4 carbon atoms or phenyl.
Claim 2
Dependent Claim
34 words
A compound having the formula: ##STR12## wherein R" is alkyl having 1 to 4 carbon atoms and R"' is alkyl of 1 to 2 carbons, alkoxy having 1 to 4 carbon atoms or phenyl.
Claim 3
Dependent Claim
10 words
The compound as in claim 1 wherein R" is ethyl.
Claim 4
Dependent Claim
14 words
The compound as in claim 2 wherein R'" is --OC 2 H 5 .
Claim 5
Dependent Claim
2 words
O,O-diethyl O-(2-(1-methylcyclopropyl)-5-pyrimidinyl)phosphorothioate.
Claim 6
Dependent Claim
2 words
O,O-diethyl O-(2-(1-methylcyclopropyl)-5-pyrimidinyl)phosphorothioate.
Claim 7
Dependent Claim
59 words
A composition for controlling corn rootworm and western spotted cucumber beetle comprising an inert agricultural carrier in admixture with an insecticidally effective amount of a pyrimidinyl phosphate having the formula: ##STR13## wherein R" is alkyl having 1 to 4 carbon atoms and R"' is alkyl of 1 to 2 carbons, alkoxy having 1 to 4 carbon atoms or phenyl.
Claim 8
Dependent Claim
59 words
A composition for controlling corn rootworm and western spotted cucumber beetle comprising an inert agricultural carrier in admixture with an insecticidally effective amount of a pyrimidinyl phosphate having the formula: ##STR13## wherein R" is alkyl having 1 to 4 carbon atoms and R"' is alkyl of 1 to 2 carbons, alkoxy having 1 to 4 carbon atoms or phenyl.
Claim 9
Dependent Claim
15 words
The composition as in claim 5 wherein the carrier contains a surface active dispersing agent.
Claim 10
Dependent Claim
20 words
The composition as in claim 5 wherein the carrier is an inert solid and the composition is in granulated form.
Claim 11
Dependent Claim
10 words
The composition as in claim 5 wherein R" is ethyl.
Claim 12
Dependent Claim
14 words
The composition as in claim 8 wherein R"' is --OC 2 H 5 .
Claim 13
Dependent Claim
15 words
The composition as in claim 5 wherein the carrier contains a surface active dispersing agent.
Claim 14
Dependent Claim
20 words
The composition as in claim 5 wherein the carrier is an inert solid and the composition is in granulated form.
Claim 15
Independent Claim
74 words
A method for controlling insects from the group consisting of corn rootworm and western spotted cucumber beetle which comprises applying to said insects, their habitats or food an insecticidally effective amount of a pyrimidinyl phosphate having the formula: ##STR14## wherein R" is alkyl having 1 to 4 carbon atoms and R'" is alkyl of 1 to 2 carbons, alkoxy having 1 to 4 carbon atoms or phenyl in admixture with an inert agricultural carrier.
Claim 16
Independent Claim
74 words
A method for controlling insects from the group consisting of corn rootworm and western spotted cucumber beetle which comprises applying to said insects, their habitats or food an insecticidally effective amount of a pyrimidinyl phosphate having the formula: ##STR14## wherein R" is alkyl having 1 to 4 carbon atoms and R'" is alkyl of 1 to 2 carbons, alkoxy having 1 to 4 carbon atoms or phenyl in admixture with an inert agricultural carrier.
Claim 17
Dependent Claim
15 words
The method as in claim 6 wherein the compound is applied as an aqueous emulsion.
Claim 18
Dependent Claim
18 words
The method as in claim 6 wherein the compound is applied in the form of a granulated composition.
Claim 19
Dependent Claim
27 words
The method as in claim 14 wherein the granulated composition is applied to a crop selected from the group consisting of corn, sorghum, cotton and sugar beets.
Claim 20
Dependent Claim
18 words
The method as in claim 6 wherein R" is ethyl and R"' is --OC 2 H 5 .
Claim 21
Dependent Claim
26 words
The method as in claim 6 wherein the compound is admixed with an inert solid, the admixture is in granulated form and is applied to corn.
Claim 22
Dependent Claim
17 words
The method as in claim 6 wherein the compound is applied to corn rootworm or its habitat.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1987-04-24 | 1987-10-24 | 1988-04-24 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1991-04-24 | 1991-10-24 | 1992-04-24 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1995-04-24 | 1995-10-24 | 1996-04-24 | $7700.00 | Window Closed / Lapsed |