PYRIMIDINE DERIVATIVES AND THEIR USE AS HERBICIDES

• US 20120053053A1
• Filed: 02/11/2010
• Published: 03/01/2012
• Est. Priority Date: 02/13/2009
• Status: Abandoned Application

• Current Assignee: Syngenta Crop Protection LLC (China National Chemical Corporation)
• Original Assignee: Syngenta Crop Protection LLC (China National Chemical Corporation)
• Inventors: Whittingham, William Guy, Boussemghoune, Mohamed Abdelouahab, Winn, Caroline Louise, Glithro, Harry, Aspinall, Mary Bernadette
• Application Number:
  US13/201,101
• Publication Number:
  US 20120053053A1
• Time in Patent Office: Days
• US Class Current: 504/103
• CPC Class Codes: A01N 43/54 1,3-Diazines; Hydrogenated 1,3-diazines
• CPC Class Codes: C07D 239/32 One oxygen, sulfur or nitrogen atom
• CPC Class Codes: C07D 239/34 One oxygen atom
• CPC Class Codes: C07D 239/36 as doubly bound oxygen atom or as unsubstituted hydroxy radical
• CPC Class Codes: C07D 239/42 One nitrogen atom nitro radicals C07D239/30

Abstract

The present invention relates to substituted pyrimidine derivatives, as well as N-oxides thereof and agriculturally acceptable salts thereof, and their use to control undesired plant growth, in particular in crops of useful plants. The invention extends to herbicidal compositions comprising such compounds, N-oxides and/or salts as well as mixtures of the same with one or more further active ingredient (such as, for example, an herbicide, fungicide, insecticide and/or plant growth regulator) and/or a safener. The invention further relates to intermediates useful in the preparation of such compounds, and to processes for their preparation.

Claims

1. A compound of formula (I)

2. The compound according to claim 1, wherein

A is halogen, C_1-4 alkylthio, phenyl optionally substituted by 1-3 groups R¹, or C_3-6 cycloalkyl optionally substituted by 1-4 groups R²;

R¹ is halogen, cyano, C_1-4 alkyl, C_1-4 haloalkyl, C_1-4 alkoxy, C_1-4 haloalkoxy, C_1-4 alkylthio, C_1-4 haloalkylthio, amino, C_1-4 alkylamino, di(C_1-4)alkylamino or two adjacent groups R¹ together with the atoms to which they are joined form a 6-membered aromatic ring, said ring being optionally substituted by 1-2 groups selected from;

halogen, cyano, C_1-4 alkyl, C_1-4 haloalkyl, C_1-4 alkoxy, C_1-4 haloalkoxy, C_1-4 alkylthio, C_1-4 haloalkylthio;

R² is halogen, cyano, C_1-4 alkyl, C_1-4 haloalkyl, C_3-6 cycloalkyl, C_1-4 alkoxy, C_1-4haloalkoxy, C_1-4 alkoxycarbonyl, or C_1-4 alkylaminocarbonyl;

or any two geminal R² groups together form a group selected from oxo, ═

CR^mmRⁿⁿ, or ═

NOR^oo;

or two groups R² together with the atoms to which they are joined form a 3-6-membered ring system, said ring system being optionally substituted by 1-2 groups selected from;

halogen, cyano, C_1-4 alkyl, C_1-4 haloalkyl, C_1-4 alkoxy, or C_1-4 haloalkoxy;

R^mm and Rⁿⁿ are each independently hydrogen, halogen, cyano, nitro, C_1-4 alkyl, or C_1-4 alkoxycarbonyl;

R^oo is hydrogen, C_1-4 alkyl, C_3-6cycloalkyl (C_1-2)alkyl or C_3-6cycloalkyl;

X is azido, halogen, C_1-3 alkoxy, C_1-4 alkoxycarbonylC_1-3alkoxy, C_1-4 alkylthio, C_1-4 alkylsulphinyl, C_1-4 alkylsulphonyl or NR⁵R⁶ wherein

R⁵ is hydrogen, C_1-4 alkyl optionally substituted with 1 or 2 C_1-4 alkoxy groups, C_1-4 haloalkyl optionally substituted with 1 or 2 C_1-4 alkoxy groups, C_2-4 alkenyl, SO₂R^ss, or C(O)R^uu;

R⁶ is hydrogen, C_1-4 alkyl optionally substituted with 1 or 2 C_1-4 alkoxy groups, or C_1-4 haloalkyl optionally substituted with 1 or 2 C_1-4 alkoxy groups, C_2-4 alkenyl;

R^ss and R^uu are C_1-3 alkyl,

Y is C_1-6 alkyl optionally substituted by 1-3 groups R^ba, C_1-6haloalkyl optionally substituted by 1-3 groups R^ba, C_3-6cycloalkyl optionally substituted by 1-3 groups R^bc, C_2-6alkenyl optionally substituted by 1-3 groups R^bd, C_2-6 alkynyl optionally substituted by 1-3 groups R^be, wherein

each R^ba is independently cyano, nitro, hydroxyl, C_3-6cycloalkyl, C_1-4 alkoxy, C_1-4alkylthio, C_1-4alkylcarbonyl or C_1-4alkoxycarbonyl, or two geminal R^ba together form an oxo or oximino group;

R^bc is halogen, cyano, C_1-4alkyl, C_1-4alkoxy, or C_1-4alkoxycarbonyl;

R^bd is halogen, cyano, C_3-6cycloalkyl, C_1-4alkylcarbonyl, or C_1-4 alkoxycarbonyl;

R^be is halogen, cyano, hydroxyl, C_1-4alkoxycarbonyl, or C_3-12 trialkylsilyl;

and,

Z is O_m—

(CH₂)_n—

C(O)R^cb, wherein n is an integer of 0 or 1, m is an integer of 0 or 1, and n=m

R^cb is hydroxyl, C_1-10 alkoxy, phenyl C_1-2 alkoxy or NH₂.

3. The compound according to claim 1 or claim 2, wherein

A is Cl, phenyl optionally substituted by 1-3 groups R¹, cyclopropyl optionally substituted by 1-2 groups R²;

each R¹ is independently halogen, cyano, C_1-2 alkyl, C_1-2 haloalkyl, C_1-2 alkoxy, C_1-2 haloalkoxy, amino, C_1-4 alkylamino, or di(C_1-4)alkylamino;

each R² is independently halogen, cyano, C_1-2alkyl, C_1-2 haloalkyl, C_1-2 alkoxy, C_1-2 haloalkoxy or C_2-4 alkoxycarbonyl;

X is N₃, Cl, OCH₃, OCH₂CO₂CH₃, NH₂, NHCH₃, N(CH₃)₂, NH-i-propyl, SMe, SOMe, SO₂Me, NHCOCH₃, NHC(O)OCH₃, NHSO₂CH₃, NCH₃COCH₃, NCH₃C(O)OCH₃, or NCH₃SO₂CH₃;

Y is C_1-3 alkyl, C_1-3 haloalkyl, C_2-5alkoxyalkyl, cyclopropyl optionally substituted by 1 or 2 groups R^bc, C_2-4 alkenyl, C_2-4 haloalkenyl, or C_2-4 alkynyl optionally substituted by 1 or 2 groups R^be, wherein

each R^bc is independently halogen or C_1-2 alkyl, and each R^be is independently halogen or C_3-9 trialkylsilyl;

and

Z is selected from the group consisting of CO₂H, CO₂CH₃, CO₂CH₂CH₃, CO₂-i-propyl, CO₂-n-propyl, CO₂CH₂-i-propyl, CO₂CH₂-Phenyl, CONH₂, OCH₂CO₂H, OCH₂CO₂CH₃.

4. The compound according to any one of the preceding claims wherein

A is selected from the group consisting of:

Cl, methylthio, isopropyl, cyclopropyl, 2-methylcyclopropyl, 4-methylphenyl, 4-methoxyphenyl, 4-chlorophenyl, 4-bromophenyl, 4-iodophenyl, 4-fluorophenyl, 4-trifluoromethylphenyl, 4-trifluoromethoxyphenyl, 2,4-dimethoxyphenyl, 2,4-dichlorophenyl, 2-chloro-4-methylphenyl, 2-chloro-4-trifluoromethylphenyl, 2-fluoro-4-methylphenyl, 2-fluoro-3-methoxyphenyl, 2-fluoro-4-methoxyphenyl, 2,4-bis(trifluoromethyl)phenyl, 3,4-dimethylphenyl, 3,4-dimethoxyphenyl, 3-chloro-4-methylphenyl, 3-chloro-4-methoxyphenyl, 3,4-dichlorophenyl, 3-chloro-4-fluorophenyl, 3-chloro-4-trifluoromethylphenyl, 3-fluoro-4-methylphenyl, 3-fluoro-4-methoxyphenyl, 4-methyl-3-nitrophenyl, 4-methoxy-2-methylphenyl, 4-chloro-2-methylphenyl, 4-chloro-3-methylphenyl, 4-chloro-2-methoxyphenyl, 4-chloro-3-methoxyphenyl, 4-chloro-3-nitrophenyl, 4-chloro-3-cyanophenyl, 4-chloro-2-fluorophenyl, 4-chloro-3-fluorophenyl, 4-chloro-2-trifluoromethylphenyl, 4-chloro-3-trifluoromethylphenyl, 4-fluoro-3-methylphenyl, 4-fluoro-3-methoxyphenyl, 4-fluoro-3-trifluoromethylphenyl, 2,4,5-trimethylphenyl, 2,3,4-trimethoxyphenyl, 2,3,4-trichlorophenyl, 2,4,5-trichlorophenyl, 2,4,6-trichlorophenyl, 2,3,4-trifluorophenyl, 2,4-dichloro-3-fluorophenyl, 3,4-dichloro-2-fluorophenyl, 4-chloro-2,3-difluorophenyl, 4-chloro-2,6-difluorophenyl, 4-chloro-3,5-difluorophenyl, 2,4-dichloro-6-fluorophenyl, 4-chloro-2-fluoro-3-methoxyphenyl, 4-chloro-2-fluoro-3-trifluoromethylphenyl, 4-chloro-3-dimethylamino-2-fluorophenyl, and 2-fluoro-3-methoxy-4-methylphenyl;

Y is selected from the group consisting of;

methyl, ethyl, isopropyl, n-propyl, prop-1-en-2-yl, prop-1-enyl, prop-2-enyl, but-1-enyl, pent-1-enyl, difluoromethyl, trifluoromethyl, hydroxymethyl, 1-hydroxyethyl, 2-hydroxyethyl, 1-methylprop-1-enyl, 2-methylprop-1-enyl, 1,2-dimethylprop-1-enyl, 3-methylbut-1-ynyl, 3-methylbut-2-enyl, 3,3-dimethylbut-1-ynyl, acetyl, formyl, methoxymethyl, 2-methoxyethyl, hydroxyiminomethyl, methoxyiminomethyl, 1-(hydroxyimino)ethyl, 1-(methoxyimino)ethyl, cyclopropyl, 1-methylcyclopropyl, 2,2-dichlorocyclopropyl, vinyl, 2-cyclopropylvinyl, 1-ethoxyvinyl, 2,2-dichlorovinyl, ethynyl, prop-1-ynyl, 2-bromoethynyl, 2-chloroethynyl, and 2-trimethylsilylethynyl.

5. A compound according to any one of claim 1, 2 or 4 wherein A is optionally substituted alkylthio.

6. A compound according to any preceding claim wherein X is azido, halogen, optionally substituted alkoxy, optionally substituted alkylthio, optionally substituted alkylsulphinyl or optionally substituted alkylsulphonyl.

7. A compound according to any preceding claim wherein n is 1.

8. A herbicidal composition comprising a compound as defined in any one of the preceding claims and at least one agriculturally acceptable formulation adjuvant or diluent.

9. The herbicidal composition according to claim 8, further comprising a crop safener.

10. A compound as defined in any one of claims 1 to 7, or a herbicidal composition according to claim 8 or claim 9, in admixture with at least one active ingredient selected from the group consisting of:

an insecticide, an acaricide, a nematocide, a molluscicide, an herbicide, a fungicide, and a plant growth regulator.

11. Use of a compound according to any one of claims 1 to 7 as a herbicide.

12. A method of controlling weeds in crops of useful plants which comprises applying to said weeds or to the locus of said weeds, or to said crop of useful plants, a compound as defined in any one of claims 1 to 7, or a herbicidal composition according to claim 8 or claim 9, or a mixture according to claim 10.

13. A compound of formula (II)

14. A process for the preparation of a compound of formula (T)

15. A process according to claim 14 comprising the further step or steps of converting the compound of formula (T) to a compound of formula (I)