IP Library Granted Patent US 8,193,198
Granted Patent B2
US 8,193,198 · App. 13/122,199 · Granted Jun 5, 2012

Uracil compounds and a herbicide comprising the same

Assignees: Korea Research Institute of Chemical Technology; Dongbu HiTek Co., Ltd.
View Patent ↗
Loading inventors, assignments & file history…
Monitor This Case
Get email alerts when status or documents change.
Order Certified Copies
Most orders are placed with the USPTO same day — all within 24 business hours.
Order via The Patent Place →
Pre-filled with this patent's details
Quick Facts
Patent No.
US 8,193,198
App. No.
13/122,199
Granted
Jun 5, 2012
Kind
B2
Abstract

Disclosed are uracil compounds represented by Formula 1, a method for preparing the compounds, and a herbicide including the same as an active ingredient: wherein R 1 , R 2 , R 3 , R 4 , R 5 , X, Y, Z and W are the same as defined in the detailed description.

Claims (40)

1. A uracil compound represented by Formula 1 or an agrochemically allowable salt thereof:

wherein

R 1 and R 2 , which may be the same or different, represent hydrogen or C 1 -C 6 alkyl;

R 3 represents hydrogen, hydroxyl, C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 1 -C 8 alkoxy, C 1 -C 6 haloalkyl, C 2 -C 6 haloalkenyl, C 1 -C 6 alkoxy C 1 -C 6 alkyl or C 6 -C 10 aryl C 1 -C 6 alkoxy;

R 4 represents hydrogen, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl or C 1 -C 6 alkoxycarbonyl C 1 -C 6 alkyl;

R 5 represents hydrogen, C 1 -C 6 alkyl, C 1 -C 6 alkoxy, C 2 -C 6 haloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 haloalkenyl, C 2 -C 6 alkynyl, C 1 -C 6 alkoxycarbonyl C 1 -C 6 alkyl, C 6 -C 10 aryl C 1 -C 6 alkyl or C 6 -C 10 aryl C 1 -C 6 alkoxy;

X represents S, SO, or SO2;

Y represents C 1 -C 6 alkylene or C 1 -C 6 haloalkylene; W represents O, S, NH or N(C 1 -C 6 alkyl); and

Z represents halogen, cyano, CONH 2 or CSNH 2 .

2. The compound according to claim 1 , wherein R 1 and R 2 , which may be the same or different, represent hydrogen or methyl;

R 3 represents hydrogen, hydroxyl, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, vinyl, allyl, methoxy, ethoxy, n-propoxy, n-butoxy, tert-butoxy, chloromethyl, dichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl or benzyloxy;

R 4 represents hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl or tert-butyl;

R 5 represents hydrogen, hydroxyl, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, vinyl, allyl, propargyl, methoxy, ethoxy, n-propoxy, n-butoxy, tert-butoxy, benzyl, phenethyl, methoxycarbonylmethyl, methoxycarbonylethyl, methoxycarbonylpropyl, ethoxycarbonylmethyl, benzyloxy or phenethyloxy;

X represents S, or SO2;

Y represents CH 2 , CH(CH 3 ), CH 2 CH 2 , CH 2 CH 2 CH 2 , CH(CF 3 ), CH(CH 2 F), CH(CHF 2 ), CH 2 CHF or CH 2 CF 2 ;

W represents O, NH or N(CH 3 ); and

Z represents chlorine, cyano, CONH 2 or CSNH 2 .

3. The compound according to claim 1 , wherein R 1 and R 2 , which may be the same or different, represent hydrogen or methyl;

R 3 represents hydrogen, hydroxyl, methyl, methoxy or benzyloxy;

R 4 represents hydrogen or methyl;

R 5 represents hydrogen, methyl, ethyl, n-propyl, n-butyl, methoxy, allyl, propargyl, benzyl, benzyloxy or methoxycarbonylmethyl;

X represents S, or SO2;

Y represents CH 2 , CH(CH 3 ), CH 2 CH 2 , CH 2 CH 2 CH 2 or CH(CH 2 F);

W represents O or NH; and

Z represents chlorine, cyano or CSNH 2 .

4. The compound according to claim 1 , which is selected from:

3-[{2-[2-chloro-5-(3,6-dihydro-3-methyl-2,6-dioxo-4-trifluoromethyl-1(2H)-pyrimidinyl)-4-fluorophenylthio]-1-oxopropyl}amino]propionic acid methyl ester (Compound No. 36);

3-[{2-[2-chloro-5-(3,6-dihydro-3 -methyl-2,6-dioxo-4-trifluoromethyl-1(2H)-pyrimidinyl)-4-fluorophenylsulfonyl]-1-oxopropyl}amino]propionic acid methyl ester (Compound No. 61); and

an agrochemically allowable salt thereof.

5. A herbicide comprising a uracil compound represented by Formula 1, an agrochemically allowable salt thereof or a mixture thereof as an active ingredient:

wherein R 1 , R 2 , R 3 , R 4 , R 5 , X, Y, Z and W are the same as defined in claim 1 .

6. The herbicide according to claim 5 , further comprising an additive, wherein the uracil compound concentration is sufficient to remove grass weeds and broadleaf weeds by foliar application.

7. The herbicide according to claim 5 , further comprising an additive, wherein the uracil compound concentration is sufficient to remove grass weeds and broadleaf weeds without damage of crops upon soil treatment.

8. A herbicidal composition comprising:

0.1 wt % to 99.9 wt % of active ingredient selected from the group consisting of a uracil compound represented by Formula 1, an agrochemically allowable salt thereof or a mixture thereof; and

0.1 wt % to 99.9 wt % of an additive selected from a surfactant and a solid or liquid diluent:

wherein

R 1 , R 2 , R 3 , R 4 , R 5 , X, Y, Z and W are the same as defined in claim 1 .

9. The herbicidal composition according to claim 8 , which is formulated into a wettable powder, a suspension concentrate, an emulsifiable concentrate, an emulsion oil in water, a microemulsion, a soluble concentrate, a dispersible liquid, a water dispersible granule, a granule or a tablet.

10. The herbicidal composition according to claim 8 , wherein the active ingredient further comprises one or more selected from the group consisting of acetyl-CoA carboxylase inhibitor (ACC), acetolactate synthase, inhibitor (ALS), amide, auxin herbicide, auxin transport inhibitor, carotenoid biosynthesis inhibitor, enolpyruvylshikimate 3-phosphate synthase inhibitor (ESPS), glutamine synthetase inhibitor, lipid biosynthesis inhibitor, mitosis inhibitor, protoporphyrinogen IX oxidase inhibitor, photosynthesis inhibitor, synergist, growth substance, cell wall biosynthesis inhibitor and known herbicide.

Assignments (4)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 4, 2022
From: FARMHANNONG CO., LTD.; KOREA RESEARCH INSTITUTE OF CHEMICAL TECHNOLOGY
To: FARMHANNONG CO., LTD.
Reel/Frame 059484/0858 →
CHANGE OF NAME Recorded Mar 18, 2022
From: DONGBU FARM HANNONG CO., LTD.
To: FARMHANNONG CO., LTD.
Reel/Frame 059451/0223 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 25, 2015
From: KOREA RESEARCH INSTITUTE OF CHEMICAL TECHNOLOGY; DONGBU HITEK CO., LTD.
To: KOREA RESEARCH INSTITUTE OF CHEMICAL TECHNOLOGY; DONGBU FARM HANNONG CO., LTD.
Reel/Frame 035028/0583 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 17, 2011
From: KO, YOUNG KWAN; CHUNG, KUN HOE; RYU, JAE WOOK; WOO, JAE CHUN; KOO, DONG WAN; KIM, DAE WHANG; KIM, TAE JOON; CHOI, IN YOUNG; KIM, YOUNG KWON; OH, TAE HYUN; CHOI, JUN HYUK; SEOK, MEE YOUNG; KIM, KYUNG SUNG; CHUNG, BONG JIN
To: KOREA RESEARCH INSTITUTE OF CHEMICAL TECHNOLOGY; DONGBU HITEK CO., LTD.
Reel/Frame 026291/0043 →
Priority Claims (1)
KR 10-2008-0097108 · Oct 2, 2008 · national
Continuity (1)
Related Publication 20110224083A1 · Sep 15, 2011