Diaryl ethers and processes for their preparation and...

Details Diaryl ethers and processes for their preparation and... Diaryl ethers and processes for their preparation and...

2000-05-15

2001-10-16

Shah, Mukund J. (Department: 1624)

Plant protecting and regulating compositions

Plant growth regulating compositions

Organic active compound containing

C504S218000, C504S230000, C504S238000, C504S243000, C504S246000, C504S253000, C504S266000, C504S269000, C504S273000, C504S281000, C544S331000, C544S219000, C544S239000, C544S300000, C540S461000, C540S476000, C540S523000, C540S593000, C546S119000, C546S275700, C548S182000, C548S184000, C548S213000, C548S360500, C548S362500

Reexamination Certificate

active

06303543

ABSTRACT:

A class of diaryl ethers and compositions thereof which are useful in the control of weeds is of the general formula
wherein
X, Y are hydrogen, halogen, cyano, nitro, or (C
1-6
)haloalkyl;
Z is oxygen or sulfur;
Q is selected from
Ar is a substituted or unsubstituted aryl or heteroaryl ring; When Q is Q
3
or Q
6
, substituted phenyl is excluded.
BACKGROUND OF THE INVENTION
Various substituted phenyl ethers (I
1
) are known in the literature.
Q may be pyrazole, imidazole, imidazolidine-2,4-dione, triazolinone, tetrazolinone, aminouracil, etc. R may be hydrogen, alkyl, cycloalkyl, alkenyl or alkynyl. U.S. Pat. No. 5,496,956 discloses arylpyrazoles with the R group selected from propargyl, allyl, or substituted alkyl. JP 6,256,312 discloses phenylimidazoles with the R group selected from hydrogen, (C
1-10
)alkyl. (C
1-5
)haloalkyl, (C
3-5
)alkenyl, (C
3-5
)alkynyl, or (C
3-6
)cycloalkyl. U.S. Pat. No. 5,125,958 discloses triazolinones with the R group selected from substituted phenyl group. JP 57,197,268 discloses hydantoins with the R group selected lower alkyl. U.S. Pat. No. 4,902,337 discloses hydantoins with the R group selected from hydrogen, alkyl, cycloalkyl, alkenyl or alkynyl. JP 525173 discloses pyrimidinediones with the R group selected from hydrogen, (C
1-10
)alkyl, (C
1-5
)haloalkyl, (C
3-5
)alkenyl, (C
3-5
)alkynyl, or (C
3-6
)cycloalkyl. U.S. Pat. No. 4,985,065 discloses phenyltetrazolinones with the R group selected from substituted phenyl group. No heteroaryl derivatives were claimed as R. WO 9,602,523 discloses substituted aryliminothiadiazoles with the R group selected from hydrogen, alkyl, cycloalkyl, alkenyl or alkynyl. U.S. Pat. No. 4,452,981 discloses phenylurazoles with the R group selected from (C
1-3
)alkyl, allyl, or propargyl. EP-A-517181(which corresponds to U.S. Pat. No. 5,280,010) discloses aminouracil compounds wherein Q is amino uracil and R is a lower alkyl group. WO96/07323 and WO96/08151 disclose some known uracil compounds. In WO96/08151 the generic representation is significantly broader than the disclosures set forth in it, and in the prior art patents. The specific aminouracil compounds of the formula (I) mentioned below are not known and are novel.
The present invention reveals that some diaryl ethers represented by the general formula (I) or their salts have a potent herbicidal activity with good crop safety.
DESCRIPTION
The need continues for novel and improved herbicidal compounds and compositions. This invention relates to novel diaryl ethers, compositions comprising diaryl ethers, and the use of diaryl ethers and compositions thereof as broad spectrum herbicides which are effective against both monocot and dicot weed species in preemergence and postemergence application and are sometimes safe to crops. The compounds and compositions of the present invention can also be sometimes used as desiccants. This invention also includes methods of preparing these compounds and intermediates thereof as well as methods of using the compound as herbicides.
This invention relates to diaryl ether compounds having the general formula I and their salts
wherein
X, Y are independently hydrogen, halogen, cyano, nitro, or (C
1-6
)haloalkyl and
Z is oxygen or sulfur and
Q is selected from
R
1
is halogen;
R
2
, R
3
, R
4
and R
5
are independently hydrogen, (C
1-6
)alkyl, or (C
1-6
)haloalkyl;
When R
3
and R
5
are taken together with the atoms to which they are attached, they represent a four to seven membered substituted or unsubstituted ring optionally interrupted by O, S(O)
n
or N—R
4
, and optionally substituted with one to three (C
1-6
)alkyl group or one or more halogen atoms;
R
6
is hydrogen, (C
1-6
)alkyl, (C
2-6
)alkenyl, (C
2-6
)alkynyl, (C
1-6
)haloalkyl, (C
2-6
)haloalkenyl, (C
2-6
)haloalkynyl, (C
1-6
)cyanoalkyl, (C
1-6
)alkoxy-(C
1-6
)alkyl, or (C
1-6
)alkylthio-(C
1-6
)alkyl;
A
1
and A
2
are independently oxygen or sulfur;
B is CH or N;
R
7
and R
8
are each independently hydrogen, (C
1-6
)alkyl optionally substituted with one or more halogen atoms, or (C
3
-C
6
)cycloalkyl optionally substituted with one or more halogen atoms, and when R
7
and R
8
are taken together with the atoms to which they are attached, they represent a four to seven membered substituted or unsubstituted ring optionally interrupted by O, S(O)
n
or N—R
4
, and optionally substituted with one to three (C
1-6
)alkyl groups or one or more halogen atoms;
n is an integer of 0, 1, or 2.
R
9
and R
10
is hydrogen, (C
1-6
)alkyl, acyl, or (C
1-6
)alkylsulfonyl or R
9
and R
10
may form a ring consisting of polymethylene, (CH
2
)
m
, groups, where m is an integer of 2, 3, 4 or 5, together with the nitrogen atom of NR
9
R
10
, which may or may not have a (C
1-6
)alkyl substituent.
D is carbon, oxygen, sulfur or a nitrogen atom, sulfoxide or sulfone;
n
1
is 0, 1, 2, or 3;
R
11
is hydrogen, hydroxyl, C
1-3
alkoxy, C
1-3
haloalkoxy, C
2-5
alkylcarbonyloxy, or C
2-5
haloalkylcarbonyloxy, nitro, or amino;
R
12
is hydrogen, hydroxyl, or halogen;
When R
11
and R
12
are bonded to the same carbon atom, they may form a carbonyl bond.
When R
11
and R
12
are bonded to adjacent carbon atoms, they may form a epoxide ring;
The ring to which R
11
and R
12
are attached may be saturated or unsaturated and may contain single or double bonds.
E—G is N═N, CH═N, N═CH, or CH═CH.
Some compounds of formula (1) 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 quarternary ammonium salt such as ammonium salt or a dimethylamine salt.
Ar is a substituted or unsubstituted aryl or heteroaryl ring; When Q is Q
3
or Q
6
, substituted or unsubstituted phenyl is excluded.
This invention also relates to compositions containing those compounds and methods for using those compounds and compositions. The compounds and compositions of the present invention are especially useful for the selective control of undesirable plant species occasionally in the presence of crops. The compounds and compositions of the present invention can also be used as desiccants.
DETAILED DESCRIPTION OF THE INVENTION
The present invention provides a method for controlling undesirable plant species by preemergence or postemergence application.
The diaryl ether compounds of this invention have the general formula I
wherein X, Y, Z, Ar, and Q are as described above.
The aryl in the definition of Ar may be phenyl or naphthyl, and the heteroaryl 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 or isothiazolyl. The substituents for the substituted aryl or heteroaryl ring may, for example, be halogen, (C
1-6
)alkyl, halo(C
1-6
)alkyl, (C
1-6
)alkoxy, halo(C
1-6
)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
)alkylcarbonylamino, bisbenzoylamino, aminoacetyl, aminotifluoroacetyl, or amino(C
1-6
)allylsulfonate. The number of substituents is one or more, for example up to five. When the number is two or more, the substituents may be same or different.
The alkyl group and alkyl part in the definition related to X, Y, R
2
to R
12
and the substituents for the substituted aryl and heteroaryl ring as Ar have the straighted or branched chains with C
1-6
, preferably C
1-4
such as methyl, ethyl, propyl, butyl, pentyl, or hexyl. The alkenyl or alkynyl group and their parts in the definition for R
6
have also

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