Processes for preparing 3-phenyl-2,4(1H, 3H)-pyrimidinediones

Details Processes for preparing 3-phenyl-2,4(1H, 3H)-pyrimidinediones Processes for preparing 3-phenyl-2,4(1H, 3H)-pyrimidinediones

2001-09-26

2003-09-09

Ford, John M. (Department: 1624)

Plant protecting and regulating compositions

Plant growth regulating compositions

Organic active compound containing

C544S296000, C544S310000, C544S312000

Reexamination Certificate

active

06617282

ABSTRACT:

TECHNICAL FIELD
A class of 3-phenyl-2,4(1H,3H)-pyrimidinediones and compositions containing them as active ingredients are useful as herbicides, defoliants and desiccants.
Background Art
It has been known, that certain 3-phenyl-2,4(1H,3H)-pyrimidinediones are useful in the control of weeds, and they can be prepared by using various processes in the literature; for example WO96/07323, WO96/08151, WO98/41093.
It has also concretely been known in WO98/41093, that the specific 3-phenyl-2,4(1H,3H)-pyrimidinediones can be produced by using the isocyanates and 3-amino or 3-hydrazino-4,4,4-trifluorocrotonate esters.
However, it has not been known therein that they can be produced by using the isocyanates and 3-substituted hydrazino-4,4,4-trifluorocrotonate esters.
Disclosure of the Invention
The need continues for novel and improved herbicidal, defoliant or desiccant compounds, and compositions containing these compounds, and further for industrial preparation process therefor. This invention relates to novel preparation processes of certain 3-phenyl-2,4(1H,3H)-pyrimidinediones represented by the general formula (I) or their salts, some compounds among them and compositions containing said some compounds for herbicides, defoliants or desiccants, and methods of using these compositions.
This invention relates to a process for producing 3-phenyl-2,4(1H,3H)-pyrimidinediones having the general formula (I) and their salts
wherein
A
1
is hydrogen, halogen, cyano, nitro, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, cyloalkynyl, cycloalkylalkyl, each being optionally substituted,
A
2
is hydrogen, —Q
1
—A
3
wherein Q
1
is O, S, SO, or SO
2
; A
3
is hydrogen or A
4
(A
4
is alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, cyloalkynyl, cycloalkylalkyl, aryl, arylalkyl, heterocyclyl, heterocyclicalkyl, each being optionally substituted), —Q
1
—CQ
2
—A
3
wherein Q
2
is O or S, —Q
1
—CQ
2
—Q
2
—A
3
, —Q
1
—CQ
2
—N(A
3
)
2
, —CQ
2
—A
3
, —CQ
2
—Q
2
—A
3
, —CQ
2
—N(A
3
)
2
, —N(A
3
)
2
, —N(Q
1
—A
3
)
2
, —N(CQ
2
—A
3
)
2
, —N(Q
1
—A
3
)(CQ
2
—A
3
), —N(CQ
2
—Q
2
—A
3
)
2
, —N(A
3
)—CQ
2
—N(A
3
)
2
, or —SO
2
—N(A
3
)
2
, each A
3
group of (A
3
)
2
being independently same or different, any two of (A
1
)l and (A
2
)m groups being optionally combined through a saturated or unsaturated carbon, —CQ
2
—, and/or hetero O, N, S, SO, or SO
2
linkages to form a cyclic ring having up to 12 membered ring, each being optionally substituted,
l is an integer of 1 to 5, m is an integer of 1 to 3, l+m is an integer of 2 to 5,
R
1
is A
4
, —Q
1
—A
3
, —Q
1
—CQ
2
—A
3
, —Q
1
—CQ
2
—Q
2
—A
3
, —Q
1
—CQ
2
—N(A
3
)
2
, —CQ
2
—A
3
, —CQ
2
—Q
2
—A
3
, —CQ
2
—N(A
3
)
2
, —N(A
3
)
2
, —N(Q
1
—A
3
)
2
, —N(CQ
2
—A
3
)
2
, —N(Q
1
—A
3
)(CQ
2
—A
3
), —N(CQ
2
—Q
2
—A
3
)
2
, —N(A
3
)—CQ
2
—N(A
3
)
2
, or —SO
2
—N(A
3
)
2
, each A
3
group of (A
3
)
2
being independently same or different,
R
2
is hydrogen or R
1
.
R
1
and R
2
groups being optionally combined together with N of N(R
1
)(R
2
) through a saturated or unsaturated carbon, —CQ
2
—, and/or hetero O, N, S, SO, or SO
2
linkages to form a cyclic ring having up to 12 membered ring, each being optionally substituted,
which comprises reacting the isocyanates represented by the general formula (II)
wherein A
1
, A
2
, l and m are as defined above, and the substituted hydrazono esters represented by the general formula (III)
wherein R
5
is A
4
, R
1
and R
2
are as defined above, with or without the presence of a base.
DETAILED DESCRIPTION OF THE INVENTION
This invention relates to said process for producing 3-phenyl-2,4(1H,3H)-pyrimidinediones having the general formula (I) and their salts.
Some compounds of the formula (I) may form a salt with an acidic substance or a basic substance. The salt with an acidic substance may be an inorganic acid salt such as hydrochloride, hydrobromide, phosphate, sulfate or nitrate. The salt with a basic substance may be a salt of an inorganic or organic base such as sodium salt, potassium salt, calcium salt, quarternary ammonium salt such as ammonium salt or dimethylamine salt.
The substituents concerning the term of “each being optionally substituted” or “substituted or unsubstituted” in the various definitions of the formulas (I), (I-a) to (I-c), (II), (II-a) to (II-c), (III), (III-a) to (III-c), may include halogen, cyano, nitro, amino, hydroxy, alkyl, haloalkyl, alkoxy, haloalkoxy, alkylthio, alkylsulfonyl, alkylsulfinyl, dialkylaminocarbonyl, alkylsulfonylamino, alkoxycarbonylalkoxy, alkylcarbonylamino, alkoxycarbonylamino, bis-acylamino, aminoacyl, aminohalogenoacyl, or aminoalkylsulfonate. Number of the substituents is one or more, when the substituents are two or more, they are same or different.
The term of “alkyl” by itself or as part of another substituent, means, unless otherwise stated, a straight or branched chain, and can include di- and multi-radicals, having number of carbon atoms designated (i.e. C
1-6
means one to six carbons). Examples of alkyl groups may include ones with C
1-6
, preferably C
1-4
such as methyl, ethyl, propyl, butyl, pentyl, or hexyl. The term of “alkenyl”, or “alkynyl” by itself or as part of another substituent, means, unless otherwise stated, a straight or branched chain, and can include di- and multi-radicals, having the number of carbon atoms designated (i.e. C
2-6
means two to six carbons). Examples of alkenyl or alkynyl groups may include ones with C
2-6
, preferably C
2-4
such as vinyl, propenyl, butenyl, pentenyl, or hexenyl; ethynyl, propynyl, butynyl, pentynyl, or hexynyl. The term of “cycloalkyl”, “cycloalkenyl” or “cycloalkynyl” by itself or as part of another substituent, means, unless otherwise stated, cyclic radicals, which may be fully saturated, mono-, or poly-unsaturated, and can include di- and multi-radicals, having the number of carbon atoms designated (i.e. C
3-12
means three to twelve carbons). Examples of cycloalkyl, cycloalkenyl or cycloalkynyl group may include ones with C
3-12
, preferably C
3-9
, more preferably C
3-6
such as cyclopropyl, cyclobutyl, cyclopentyl, or cyclohexyl; cyclopropenyl, cyclobutenyl, cyclopentenyl, or cyclohexenyl; cyclopropynyl, cyclobutynyl, cyclopentynyl, or cyclohexynyl.
The term of “acyl” by itself or as part of another substituent, means, unless otherwise stated, a group represented by the formula “—CQ
2
—A
4
.
The term of “halogen” by itself or as part of another substituent, means, unless otherwise stated, fluorine, chlorine, bromine, or iodine. For example, haloalkyl or haloalkoxy group constitutes the alkyl or alkoxy and one or more halogen atoms as mentioned above. When the number of halogen atom is two or more, halogen atoms may be independently same or different.
The substituted hydrazono esters may include the compounds of the formulas (111), (111-1), (111-a) to (111-c) and their isomers; for example, the compounds are represented by the general formula (111)
and their isomers are represented by the general formula (111
1
)
The bases to be used in the processes of the present invention may include inorganic bases such as alkali metals or alkali earth metals, their hydrides, alkoxides, hydroxides or carbonates; metallic sodium, and alkyl lithiums e.g. butyl lithium lithium hydride, sodium hydride, sodium methoxide, sodium hydroxide, potassium hydroxide, calcium hydroxide, magnesium hydroxide, calcium carbonate; Grignard Reagents such as (C
1-6
) alkyl or aryl magnesium halide such as methyl magnesium bromide, ethyl magnesium bromide, n-propyl magnesium bromide, phenyl magnesium bromide, methyl magnesium chloride, dialkyl magnesium, preferably Grignard Reagents, more preferably methyl magnesium bromide; or an organic base such as mono, di, or trialkylamines or alkanolamines (e.g. monomethylamine, dimethylamine, trimethylamine, triethylamine, triethanolamine etc.), pyridine, lutidine, etc.
1) The preferred processes of the invention are as follows.
A process for producing 3-(3-substituted phenyl)-2,4(1H,3H)-pyrimidinediones having the general formula (I-a) and their salts
wherein
X, Y are hydrogen, h

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