Aryl ether derivatives and processes for their preparation...

Details Aryl ether derivatives and processes for their preparation... Aryl ether derivatives and processes for their preparation...

2001-12-05

2003-09-02

Raymond, Richard L. (Department: 1624)

Plant protecting and regulating compositions

Plant growth regulating compositions

Organic active compound containing

C504S243000, C544S309000, C544S317000, C544S180000, C544S182000, C544S224000, C548S360100, C548S356100

Reexamination Certificate

active

06613718

ABSTRACT:

TECHNICAL FIELD
The present invention relates to a class of aryl ether derivatives useful as herbicides and desiccants.
BACKGROUND OF THE INVENTION
Various substituted phenyl ethers (I′) are known in literature. Q may be uracil, triazine, pyridazine, pyrazole, etc., R may be hydrogen, alkyl, cycloalkyl, alkenyl, or alkynyl. WO 98/41093 and U.S. Pat. No. 6,121,201 describe certain diaryl ethers as herbicides. WO 00/50409 describes herbicidal compounds containing 1-aryl-1,3,5-triazine-4-thione-2,6-dione derivatives. WO 99/14201 describes certain 2-phenyl-3(2H)-pyridazinone derivatives and WO 99/59983 describes certain 6-aryl-3,5-dithioxo-2,3,4,5-tetrahydro-1,2,4-triazine and 6-aryl-3-thioxo-5-oxo-2,3,4,5-tetrahydro-1,2,4-triazine derivatives as herbicides. WO 96/15115 and WO 00/12480 describes a group of substituted phenyl pyrazole derivatives as herbicides. WO 93/15074 and U.S. Pat. No. 5,670,455 describe certain aryl substituted fused pyrazole derivatives as herbicides.
WO96/07323 and WO96/08151 disclose some known uracil compounds. In WO96/07323 and WO96/08151, the generic representation is significantly broader than the disclosures set forth in them, and in the prior art patents.
However the specific aryl ether compounds of the formula (I) mentioned below are not known and are novel. Furthermore the present invention reveals that the aryl ether derivatives represented by the general formula (I) or their salts have potent herbicidal activity and/or desiccant activity with good crop safety.
SUMMARY OF THE INVENTION
This invention relates to aryl ether derivatives represented by the following general formula (I) and their salts:
wherein X and Y are independent of each other and are represented by hydrogen, halogen, cyano, nitro, (C
1-4
)alkyl, (C
1-4
)haloalkyl, or (C
1-4
)haloalkoxy;
Z is oxygen or sulfur;
Q is
 A is oxygen, sulfur, or imino;
R
1
is hydrogen, (C
1-4
)alkyl, or (C
1-4
)haloalkyl, and can be independent of each other;
R
2
and R
3
are independent of each other and may be selected from the group consisting of hydrogen, halogen, cyano, nitro, (C
1-4
)alkyl, (C
1-4
)haloalkyl, (C
2-6
)alkenyl, (C
2-6
)haloalkenyl and amino which may be optionally substituted with (C
1-4
)alkyl or (C
1-4
)haloalkyl;
Ar is substituted or unsubstituted carbocyclic or heterocyclic aromatic ring being at least a five or six membered ring. This ring can be fused with another substituted or unsubstituted five or six membered carbocyclic or heterocyclic ring; when Q is Q5, unsubstituted or substituted phenyl is excluded.
This invention also relates to herbicidal and/or desiccant compositions containing them, and to methods for using these compositions. Further this invention sometimes relates to methods for the control of undesired vegetation in a plantation crop by the application to the locus of the crop an effective amount of the compounds described herein, as broad spectrum herbicides which are effective against a variety of weed species in pre emergence and post emergence applications with crop safety. Furthermore this invention relates to methods for preparing these compounds and intermediates thereof
DETAILED DESCRIPTION OF THE INVENTION
The present invention provides the aryl ether compounds having the general formula (I) and salts thereof
wherein X, Y, Z, Ar, and Q are as described above.
The aryl in the definition of Ar may be a substituted or unsubstituted carbocyclic or heterocyclic aromatic ring being at least a five or six membered ring. This ring can be fused with another substituted or unsubstituted five or six membered carbocyclic or heterocyclic aromatic ring. For example, the carbocyclic aromatic ring in the definition of Ar may be aryl such as phenyl or naphthyl, and the heterocyclic aromatic ring in the definition of Ar may be a five or six membered ring having at least one heterogeneous atom of nitrogen, oxygen or sulfur, and for example may be pyridyl, pyrimidyl, pyridazinyl, triazolyl, thiazolyl, isothiazolyl, quinoline, or isoquinoline. The substituents for the substituted carbocyclic or heterocyclic aromatic ring in the definition of Ar may, for example, be halogen, (C
1-6
)alkyl, halo(C
1-6
)alkyl, (C
1-6
)alkoxy, halo(C
1-4
))alkoxy, (C
1-6
)alkylthio, (C
1-6
)alkylsulfonyl, (C
1-6
)alkylsulfinyl, (C
1-6
)dialkylaminocarbonyl, cyano, nitro, amino, hydroxy, (C
1-6
)alkylsulfonylamino, (C
1-6
)alkoxycarbonyl(C
1-6
)alkoxy, (C
1-6
)alkoxycarbonyl-halo(C
1
6
)alkyl, (C
2-6
)alkenyloxycarbonyl(C
1-6
)alkoxy(C
1-6
)alkyl, (C
1-6
)alkylcarbonylamino, bisbenzoylamino, aminoacetyl, aminotrifluoroacetyl, or amino(C
1-6
)allylsulfonate. The number of substituents therefor is one or more, for example up to seven. When the number is two or more, the substituents may be same or different. When Q is Q5, unsubstituted or substituted phenyl is excluded.
Some compounds of formula (I) and their intermediates may occasionally exist as geometrical or optical isomers and the present invention includes all of these isomeric forms. Some compounds of the formula (I) and their intermediates 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 a hydrochloride, a hydrobromide, a phosphate, a sulfate or a nitrate. The salt with a basic substance may be a salt of an inorganic or organic base such as a sodium salt, a potassium salt, a calcium salt, a quaternary ammonium salt such as ammonium salt or a dimethylamine salt.
The alkyl group and alkyl part in the definition related to X, Y, R
1
to R
3
and the substituents for the substituted aryl and heteroaryl ring as Ar have straight or branched chains with C
1-6
, preferably C
1-4
such as methyl, ethyl, propyl, butyl, pentyl, or hexyl. The alkenyl group and their parts in the definition for R
2
and R
3
have also straight or branched chains with C
2-6
, preferably C
2-4
such as vinyl, propenyl, butenyl, pentenyl or hexenyl.
The halogen atom and halogeno part in the definition related to X, Y, and R
1
to R
3
are fluorine, chlorine, bromine, or iodine. The haloalkyl or haloalkenyl group constitutes the alkyl or alkenyl group and one or more halogen atoms as mentioned above. When the number of halogen atom is two or more, halogen atoms may be same or different.
Preferred formula (I) compounds of this invention are those wherein
X, and Y are independently hydrogen, or halogen;
Z is oxygen or sulfur;
Q is selected from Q1, Q2, Q5, or Q6
Ar is pyridyl, pyrimidyl, triazolyl, thiazolyl, isothiazolyl, or phenyl; or each of pyridyl, pyrimidyl, triazolyl, thiazolyl, isothiazolyl, or phenyl being substituted with up to five substituents independently selected from bromine, chlorine, fluorine, iodine, (C
1
-C
4
)alkyl, halo(C
1-4
)alkyl, (C
1-4
)alkoxy, (C
1-4
)alkylthio, halo(C
1-4
)alkoxy, (C
1
-C
4
)alkylsulfonyl, (C
1
-C
3
)alkylsulfinyl, di(C
1-4
)alkylaminocarbonyl, cyano, nitro, amino, hydroxy, (C
1-4
)alkylsulfonylamino, (C
1-4
)alkoxycarbonyl(C
1-4
)alkoxy, or (C
1-4
)alkoxycarbonylamino. When Q is Q5, unsubstituted or substituted phenyl is excluded.
The most preferred formula (I) compounds of this invention are those wherein
X is fluorine;
Y is chlorine;
Z is oxygen or sulfur;
Q is selected from Q1, Q2, or Q5.
Ar is 2-pyridyl, 3-pyridyl, 4-pyridyl, 3-bromo-2-pyridyl, 5-bromo-2-pyridyl, 6-bromo-2-pyridyl, 3-chloro-2-pyridyl, 5-chloro-2-pyridyl, 6-chloro-2-pyridyl, 3-fluoro-2-pyridyl, 5-fluoro-2-pyridyl, 6-fluoro-2-pyridyl, 3-cyano-2-pyridyl, 5-cyano-2-pyridyl, 6-cyano-2-pyridyl, 3-nitro-2-pyridyl, 5-nitro-2-pyridyl, 6-nitro-2-pyridyl, 3-trifluoromethyl-2-pyridyl, 4-trifluoromethyl-2-pyridyl, 5-trifluoromethyl-2-pyridyl, 6-trifluoromethyl-2-pyridyl, 5-amino-2-pyridyl, 3-dimethylaminocarbonyl-2-pyridyl, 3-methylsulfonyl-2-pyridyl, 3-isopropylsulfonyl-2-pyridyl, 6-chloro-3-trifluoromethyl-2-pyridyl, 3,5,6-trifluoropyridyl, 2-pyrimidyl, 4-pyrimidyl, 5-bromo-2-pyrimidyl, 4-chloro-2-pyrimidyl, 4-trifluoromethyl-2-pyrimidyl, 4,6-dimethoxy-2-pyrimidyl, 2,6-dimethoxy-4-pyrimidyl, 4,6-dimethoxy-2-triazinyl, phenyl, 2-iodophenyl, 2-trifluoromethoxyphenyl

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