5-fluoro-4-imino-3(alkyl/substituted alkyl)-1-(arylsulfonyl)-3,4-dihydropyrimidin-2(1H)-one and processes for their preparation

Patent metadata

Field	Value
Publication number	US-10919864-B2
Application number	US-202016741026-A
Country	US
Kind code	B2
Filing date	Jan 13, 2020
Priority date	Dec 31, 2013
Publication date	Feb 16, 2021
Grant date	Feb 16, 2021

Abstract

Provided herein are 5-fluoro-4-imino-3-(alkyl/substituted alkyl)-1-(arylsulfonyl)-3,4-dihydropyrimidin-2(1H)-one and processes for their preparation which may include the use of an alkali carbonate and an alkylating agent

First claim

What is claimed is:

1. A compound of Formula III:

wherein R 1 is

and
R 2 is selected from the group consisting of

or a tautomer, an optical isomer, or a salt thereof.

2. The compound of claim 1 in the form of a salt.

3. The compound of claim 2 , wherein the salt is a hydrochloride, hydrobromide or hydroiodide.

4. The compound of claim 1 , wherein R 2 is

5. The compound of claim 4 in the form of a salt.

6. The compound of claim 5 , wherein the salt is a hydrochloride, hydrobromide or hydroiodide.

7. The compound of claim 1 , wherein R 2 is

8. The compound of claim 7 in the form of a salt.

9. A method for control or prevention of fungal attack on a plant comprising applying a fungicidally effective amount of a compound of Formula III:

to at least one of the plant, an area adjacent to the plant, soil adapted to support growth of the plant, a root of the plant, foliage of the plant, and a seed adapted to produce the plant so as to thereby control or prevent fungal attack on the plant, wherein R 1 is

and
R 2 is selected from the group consisting of

or a tautomer, an optical isomer, or a salt thereof.

10. The method of claim 9 , wherein the fungal pathogen is Apple Scab ( Venturia inaequalis ), Leaf Blotch of Wheat ( Septoria tritici ), Leaf spot of sugarbeets ( Cercospora beticola ), Leaf Spot of peanut ( Cercospora arachidicola ), or Black Sigatoka ( Mycosphaerella fijiensis ).

11. The method of claim 9 , wherein R 2 is

12. The method of claim 11 , wherein the compound is in the form of a salt.

13. The method of claim 12 , wherein the salt is a hydrochloride, hydrobromide or hydroiodide.

14. The method of claim 9 , wherein R 2 is

15. The method of claim 9 , wherein the method further comprises applying an adjuvant surfactant.

16. The method of claim 15 , wherein the adjuvant surfactant is selected from the group consisting of: ethoxylated nonyl phenols; ethoxylated synthetic or natural alcohols; salts of the esters or sulphosuccinic acids; ethoxylated organosilicones; ethoxylated fatty amines; blends of surfactants with mineral or vegetable oils; crop oil concentrate (mineral oil (85%)+emulsifiers (15%)); nonylphenol ethoxylate; benzylcocoalkyldimethyl quaternary ammonium salt; blend of petroleum hydrocarbon, alkyl esters, organic acid, and anionic surfactant; C 9 -C 11 alkylpolyglycoside; phosphated alcohol ethoxylate; natural primary alcohol (C 12 -C 16 ) ethoxylate; di-sec-butylphenol EO-PO block copolymer; polysiloxane-methyl cap; nonylphenol ethoxylate+urea ammonium nitrrate; emulsified methylated seed oil; tridecyl alcohol (synthetic) ethoxylate (8EO); tallow amine ethoxylate (15 EO); and PEG(400) dioleate-99.

17. A fungicidal composition comprising a compound of Formula III:

wherein R 1 is

and
R 2 is selected from the group consisting of

or a tautomer, an optical isomer, or a salt thereof,
and a phytologically acceptable carrier material.

18. The composition of claim 17 , wherein R 2 is

19. The composition of claim 17 , wherein R 2 is

20. The composition of claim 17 , wherein the composition further comprises an adjuvant surfactant.

Assignees

• Adama Makhteshim Ltd

Inventors

• Choy Nakyen
• Ross Jr Ronald

Classifications

• C07D409/06

  linked by a carbon chain containing only aliphatic carbon atoms · CPC title

• C07D333/10

  Thiophene · CPC title

• C07D239/47 Primary

  One nitrogen atom and one oxygen or sulfur atom, e.g. cytosine · CPC title

• C07D239/24 Primary

  having three or more double bonds between ring members or between ring members and non-ring members · CPC title

• A01N43/54

  1,3-Diazines; Hydrogenated 1,3-diazines · CPC title