US4654329A
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US
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Insecticidal, miticidal or nematocidal phosphorus esters of 5-pyrimidinols
Assignee: Dow Chemical Co
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Filing: 1985-06-05
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Granted: 1987-03-31
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Expires: 2005-06-05
Abstract
Abstract Compounds of the formula: ##STR1## wherein R is hydrogen; alkyl of 1 to 8 carbons; alkylthiomethyl, alkylsulfinylmethyl or alkylsulfonylmethyl wherein alkyl contains 1 to 4 carbons; phenyl; phenylthio; alkylthio, alkylsulfinyl or alkylsulfonyl wherein alkyl contains 1 to 4 carbons; or alkylthioethylthio wherein alkyl contains 1 to 2 carbons; R' is hydrogen, methyl or alkylthio of 1 to 2 carbons; R" is hydrogen or methyl; X is oxygen or sulfur; R'" is alkyl of 1 to 2 carbons; and R"" is --OR"' or --S-alkyl of 1 to 4 carbons, are highly useful insecticides which are particularly valuable when applied to the soil, but are also useful applied to foliage of crops or trees. Especially good control is obtained of corn rootworm, codling moth, thrips, leafhoppers, and nematodes. 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 2,000 ppm for foliar applications.
Inventors
- 👤 Walter Reifschneider
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-06 10:09
CPC Classifications
A; A01; A01N; A01N57/00; A01N57/10; A01N57/16; C; C07; C07F; C07F9/00; C07F9/02; C07F9/547; C07F9/645; C07F9/6509; C07F9/6512
Claims Analysis
Total Claims: 37
Claim 1
Independent Claim
61 words
A compound of the formula: ##STR5## wherein R is phenylthio; alkylthio, alkylsulfinyl or alkylsulfonyl wherein alkyl contains 1 to 4 carbons; or alkylthioethylthio wherein alkyl contains 1 to 2 carbons; R' is hydrogen, methyl or alkylthio of 1 to 2 carbons; R" is hydrogen; X is oxygen or sulfur; R'" is alkyl of 1 to 2 carbons; and R"" is --OR"'.
Claim 2
Dependent Claim
61 words
A compound of the formula: ##STR5## wherein R is phenylthio; alkylthio, alkylsulfinyl or alkylsulfonyl wherein alkyl contains 1 to 4 carbons; or alkylthioethylthio wherein alkyl contains 1 to 2 carbons; R' is hydrogen, methyl or alkylthio of 1 to 2 carbons; R" is hydrogen; X is oxygen or sulfur; R'" is alkyl of 1 to 2 carbons; and R"" is --OR"'.
Claim 3
Dependent Claim
14 words
The compound as in claim 1 wherein X is sulfur, and R'" is ethyl.
Claim 4
Dependent Claim
10 words
The compound as in claim 2 wherein R' is hydrogen.
Claim 5
Dependent Claim
13 words
The compound of claim 1 wherein R is 1-methylethylthio and X is sulfur.
Claim 6
Dependent Claim
13 words
The compound of claim 1 wherein R is methylthio and X is sulfur.
Claim 7
Dependent Claim
21 words
The compound as in claim 2 wherein R is phenylthio, R' is hydrogen and R"" is --OC 2 H 5 .
Claim 8
Dependent Claim
19 words
The compound as in claim 2 wherein R is alkylsulfinyl of 1 to 4 carbons and R' is hydrogen.
Claim 9
Dependent Claim
19 words
The compound as in claim 2 wherein R is alkylthio of 1 to 4 carbons and R' is hydrogen.
Claim 10
Dependent Claim
21 words
The compound as in claim 2 wherein R is alkylthio of 1 to 4 carbons and R' is CH 3 .
Claim 11
Dependent Claim
21 words
The compound as in claim 2 wherein R is alkylsulfonyl having alkyl of 1 to 4 carbons and R' is hydrogen.
Claim 12
Dependent Claim
2 words
O,O-diethyl O-(2-methylthio-5-pyrimidinyl)phosphorothioate.
Claim 13
Dependent Claim
2 words
O,O-diethyl O-(2-methylthio-5-pyrimidinyl)phosphorothioate.
Claim 14
Dependent Claim
2 words
O,O-dimethyl O-(2-((1-methylethyl)thio)-5-pyrimidinyl)phosphorothioate.
Claim 15
Dependent Claim
2 words
O,O-dimethyl O-(2-((1-methylethyl)thio)-5-pyrimidinyl)phosphorothioate.
Claim 16
Dependent Claim
2 words
O,O-diethyl O-(2-((1-methylethyl)thio)-5-pyrimidinyl)phosphorothioate.
Claim 17
Dependent Claim
2 words
O,O-diethyl O-(2-((1-methylethyl)thio)-5-pyrimidinyl)phosphorothioate.
Claim 18
Dependent Claim
101 words
An insecticidal, miticidal or nematicidal composition comprising an agricultural carrier selected from the group consisting of surface active dispersing agents and finely divided inert solids in admixture with at least an insecticidally, miticidally or nematocidally effective amount of a pyrimidinyl phosphate having the formula: ##STR6## wherein R is phenylthio; alkylthio, alkylsulfinyl or alkylsulfonyl wherein the alkyl contains 1 to 4 carbons; or alkylthioethylthio wherein alkyl contains 1 to 2 carbons; R' is hydrogen, methyl or alkylthio of 1 to 2 carbons; R" is hydrogen; X is oxygen or sulfur; R'" is alkyl of 1 to 2 carbons; and R"" is --OR"'.
Claim 19
Dependent Claim
101 words
An insecticidal, miticidal or nematicidal composition comprising an agricultural carrier selected from the group consisting of surface active dispersing agents and finely divided inert solids in admixture with at least an insecticidally, miticidally or nematocidally effective amount of a pyrimidinyl phosphate having the formula: ##STR6## wherein R is phenylthio; alkylthio, alkylsulfinyl or alkylsulfonyl wherein the alkyl contains 1 to 4 carbons; or alkylthioethylthio wherein alkyl contains 1 to 2 carbons; R' is hydrogen, methyl or alkylthio of 1 to 2 carbons; R" is hydrogen; X is oxygen or sulfur; R'" is alkyl of 1 to 2 carbons; and R"" is --OR"'.
Claim 20
Dependent Claim
28 words
The composition as in claim 14 wherein the pyrimidinyl phosphate is present in an amount of from about 0.05 to about 98% by weight of the total composition.
Claim 21
Dependent Claim
16 words
The composition as in claim 15 wherein the agricultural carrier is a finely divided inert solid.
Claim 22
Dependent Claim
21 words
The composition as in claim 16 wherein the finely divided solid has been granulated and the pyrimidinyl phosphate compound imbibed therein.
Claim 23
Dependent Claim
21 words
The composition as in claim 16 wherein the composition contains about 2.5 to about 15% by weight of pyrimidinyl phosphate compound.
Claim 24
Dependent Claim
18 words
The composition as in claim 18 wherein the pyrimidinyl phosphate is O,O-diethyl O-(2-(methylthio)-5-pyrimidinyl)phosphorothioate O,O-dimethyl O-(2-((1-methylethyl)thio)-5-pyrimidinyl)phosphorothioate or O,O-diethyl O-(2-((1-methylethyl)thio-5-pyrimidinyl)phosphorothioate.
Claim 25
Dependent Claim
13 words
The composition as in claim 15 in the form of an emulsion concentrate.
Claim 26
Independent Claim
89 words
A method which comprises applying to insects, mites or nematodes, their habitats and food an insecticidal, miticidal or nematocidal amount but less than a phytotoxic amount of a pyrimidinyl phosphate having the formula: ##STR7## wherein R is phenylthio; alkylthio, alkylsulfinyl or alkylsulfonyl wherein alkyl contains 1 to 4 carbons; or alkylthioethylthio wherein alkyl contains 1 to 2 carbons; R' is hydrogen, methyl or alkylthio of 1 to 2 carbons; R" is hydrogen; X is oxygen or sulfur; R'" is alkyl of 1 to 2 carbons; and R"" is --OR"'.
Claim 27
Independent Claim
89 words
A method which comprises applying to insects, mites or nematodes, their habitats and food an insecticidal, miticidal or nematocidal amount but less than a phytotoxic amount of a pyrimidinyl phosphate having the formula: ##STR7## wherein R is phenylthio; alkylthio, alkylsulfinyl or alkylsulfonyl wherein alkyl contains 1 to 4 carbons; or alkylthioethylthio wherein alkyl contains 1 to 2 carbons; R' is hydrogen, methyl or alkylthio of 1 to 2 carbons; R" is hydrogen; X is oxygen or sulfur; R'" is alkyl of 1 to 2 carbons; and R"" is --OR"'.
Claim 28
Dependent Claim
23 words
The method as in claim 21 wherein the pyrimidinyl phosphate is applied in the form of an admixture containing surface active dispersing agent.
Claim 29
Dependent Claim
23 words
The method as in claim 21 wherein the pyrimidinyl phosphate is applied in the form of an admixture with finely divided inert solids.
Claim 30
Dependent Claim
14 words
The method as in claim 23 wherein the composition employed is in granular form.
Claim 31
Dependent Claim
27 words
The method as in claim 22 wherein the admixture is applied to the soil of a field crop selected from corn, sorghum, cotton, potatoes and sugar beets.
Claim 32
Dependent Claim
18 words
The method as in claim 22 wherein the composition is applied foliarly to field crops or orchard trees.
Claim 33
Dependent Claim
31 words
The method as in claim 25 wherein the composition is applied at an effective but less than phytotoxic amount in the range of about 0.1 to about 5 pounds per acre.
Claim 34
Dependent Claim
33 words
The method as in claim 26 wherein the composition is applied at an effective concentration but less than a phytotoxic amount in the range of about 6 to about 400 parts per million.
Claim 35
Dependent Claim
20 words
The method as in claim 26 wherein the composition is applied to orchard trees for the control of codling moth.
Claim 36
Dependent Claim
19 words
The method according to claim 21 wherein the pyrimidinyl phosphate compound is O,O-diethyl O-(2-methylthio-5-pyrimidinyl)phosphorothioate, O,O-dimethyl O-(2-((1-methylethyl)thio)-5-pyrimidinyl)phosphorothioate, or O,O-diethyl O-(2-((1-methylethyl)thio)-5-pyrimidinyl)phosphorothioate.
Claim 37
Dependent Claim
21 words
The composition as in claim 17 wherein the composition contains about 2.5 to about 15% by weight of pyrimidinyl phosphate compound.
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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) | 1990-03-30 | 1990-09-29 | 1991-03-31 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1994-03-30 | 1994-09-29 | 1995-03-31 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1998-03-30 | 1998-09-29 | 1999-03-31 | $7700.00 | Window Closed / Lapsed |