Herbicidal imidazolidinetrione and thioxo-imidazolidinediones

Details Herbicidal imidazolidinetrione and thioxo-imidazolidinediones Herbicidal imidazolidinetrione and thioxo-imidazolidinediones

2000-04-18

2002-09-03

Raymond, Richard L. (Department: 1624)

Plant protecting and regulating compositions

Plant growth regulating compositions

Organic active compound containing

C504S222000, C504S237000, C504S238000, C504S243000, C504S248000, C504S270000, C504S273000, C504S275000, C504S282000, C504S285000, C504S100000, C504S229000, C504S225000, C544S105000, C544S152000, C544S051000, C544S092000, C548S221000, C548S466000, C548S180000, C548S361100, C549S362000, C549S434000, C549S446000

Reexamination Certificate

active

06444615

ABSTRACT:

This invention relates to 1-substituted-phenyl-3-substituted-2-thioxo-4,5-imidazolidinediones and 2,4,5-imidazolidinetriones which have activity as herbicides, to compositions which contain these compounds and to methods of use of these compounds. In particular, the present invention pertains to 2-thioxo-4,5-imidazolidinediones or 2,4,5-imidazolidinetriones wherein a substituted phenyl ring is linked to the heterocyclic ring.
Certain 1-substituted phenyl-2-thioxo-4,5-imidazolidinediones and 2,4,5-imidazolidinetriones are known aldose reductase inhibitors (see U.S. Pat. No. 4,985,453), agricultural herbicides (see U.S. Pat. Nos. 2,895,817, 3,418,334, and 4,283,547), agricultural fungicides (see Japanese Patent disclosure 53018569), and agricultural insecticides (see International Patent Application No. WO 93/22289 A1). However, there is still a need for herbicidal compounds which have superior efficacy over those already known in the art.
We have discovered that certain compounds of this invention are surprisingly effective as pre-emergent and post-emergent herbicides. These compounds are represented by formula I
wherein
R is hydrogen, (C
1
-C
8
)alkyl, (C
3
-C
6
)cycloalkyl, (C
2
-C
6
)alkenyl, (C
3
-C
6
)alkynyl, (C
1
-C
4
)alkoxy(C
1
-C
4
)alkyl, (C
3
-C
6
)cycloalkoxy(C
1
-C
4
)alkyl, (C
2
-C
6
)alkenyloxy(C
1
-C
4
)alkyl, (C
3
-C
6
)alkynyloxy(C
1
-C
4
)alkyl, (C
1
-C
12
)alkylcarbonyl, (C
1
-C
4
)alkoxycarbonyl, (C
2
-C
6
)alkenyloxycarbonyl, cyano, dialkylamino, or (C
1
-C
6
)alkylsulfonyl;
X
1
is hydrogen or halo;
X
2
is halo, cyano, or nitro;
X
4
is hydrogen or halo;
X
3
is (C
1
-C
8
)haloalkyl, (C
1
-C
8
)alkoxy, (C
3
-C
6
)cycloalkoxy, (C
2
-C
6
)alkenyloxy, (C
3
-C
6
)alkynyloxy, (C
1
-C
12
)alkylcarbonyl, (C
1
-C
4
)alkoxycarbonyl, (C
2
-C
6
)alkenyloxycarbonyl, (C
3
-C
6
)alkynyloxycarbonyl, (C
1
-C
8
)alkylsulfonylamino, (C
1
-C
8
)alkylsulfonylalkylamino, (C
1
-C
4
)alkoxycarbonylmethoxy, (C
1
-C
4
)alkoxycarbonylethoxy; or Q;
 wherein Q is
wherein R
1
is NH
2
, OH, or (C
1
-C
4
)alkyl; and each W is independently oxygen or sulfur;
or, when X
1
is halo and X
4
is hydrogen, then X
2
and X
3
may form a 5- or 6-membered heterocyclic ring fused to the phenyl ring to form a bicyclic moiety of the formula:
wherein
L is oxygen or sulfur;
R
2
is hydrogen or (C
1
-C
4
)alkyl;
R
3
is hydrogen; (C
1
-C
6
)alkyl, (C
1
-C
6
)haloalkyl, (C
2
-C
6
)alkenyl, (C
3
-C
6
)alkynyl; (C
1
-C
4
)alkoxyalkyl; (C
2
-C
6
)alkenyloxyalkyl; (C
3
-C
6
)alkynyloxyalkyl; cyanoalkyl; amino, or hydroxy; R
4
is hydrogen, (C
1
-C
3
)alkyl, or fluorine;
or when X
1
and X
2
are halo, then X
3
and X
4
form a 5- or 6-membered heterocyclic ring fused to the phenyl ring to which they are attached to form a bicyclic moiety having the structure
wherein
Y is oxygen, sulfur or —NR
6
wherein R
6
is hydrogen, (C
1
-C
6
)alkyl, (C
3
-C
5
)alkenyl or (C
3
-C
6
)alkynyl;
Y′ is oxygen, sulfur, —NR
6
, or —CO;
R
5
is hydrogen, halo, (C
1
-C
6
)alkyl, (C
3
-C
6
)cycloalkyl, (C
2
-C
6
)alkenyl, or (C
3
-C
6
)alkynyl, (C
1
-C
6
)haloalkyl, (C
1
-C
6
)alkoxy, cyano, (C
1
-C
6
) hydroxyalkyl, —CO
2
R
8
, a formyl group, an acyl group, (C
1
-C
6
)alkylthio, (C
1
-C
6
)alkylsulfinyl, (C
1
-C
6
)alkylsulfonyl, (C
1
-C
6
)haloalkylthio, (C
1
-C
6
)haloalkylsulfinyl, (C
1
-C
6
)haloalkylsulfonyl, or a carboxyl group;
R
6
is hydrogen, (C
1
-C
6
)alkyl, (C
3
-C
6
)alkenyl, or (C
3
-C
6
)alkynyl;
R
7
is hydrogen, halo, (C
1
-C
6
)alkyl, (C
1
-C
6
)haloalkyl, an acyl group, or a nitro;
and agronomically acceptable salts thereof.
The term “alkyl” includes both branched and straight chain alkyl groups such as, for example, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, n-hexyl, n-heptyl, isooctyl, nonyl, decyl, undecyl, dodecyl and the like. The term “cycloalkyl” refers to a cyclic aliphatic ring structure such as cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclooctane and the like. The term “haloalkyl” refers to an alkyl group substituted with one or more halo groups. The term “halo” refers to fluoro, chloro, bromo or iodo.
The term “alkylsulfonylalkyl” refers to an alkyl group substituted with an alkylsulfonyl (alkyl-SO
2
) group, for example methylsulfonylmethyl. The term “alkylsulfinylalkyl” refers to an alkyl group substituted with an alkylsulfinyl (alkyl-SO) group, for example methylsulfinylmethyl.
The term “alkenyl” refers to an ethylenically unsaturated hydrocarbon group, straight or branched, having 1 or 2 ethylenic bonds. The term “haloalkenyl” refers to an alkenyl group substituted with one or more halo groups. The term “alkynyl” refers to an unsaturated hydrocarbon group, straight or branched, having 1 or 2 acetylenic bonds. The term “alkoxy” includes both branched and straight chain alkyl groups attached to a terminal oxygen atom such as, for example, methoxy, ethoxy, n-propoxy, isopropoxy, tert-butoxy and the like. The term “haloalkoxy” refers to an alkoxy group substituted with one or more halo groups.
The term “alkylthio” includes both branched and straight chain alkyl groups attached to a terminal sulfur atom. The term “haloalkylthio” refers to an alkylthio group substituted with one or more halo groups.
Agronomically acceptable salts may be formed by complexation of the compounds of the current invention with metal salts such as zinc chloride or iron chloride.
For purposes of this invention, unless otherwise indicated, all percentages, parts, and ratios are by weight and all ranges are inclusive and combinable.
Preferred compounds are compounds of formula I, wherein W is oxygen or sulfur; R is, (C
1
-C
6
)alkyl, (C
1
-C
4
)haloalkyl, (C
4
-C
6
)cycloalkyl, (C
2
-C
5
)alkenyl, (C
3
-C
6
)alkynyl, (C
1
-C
3
)alkoxyalkyl, (C
4
-C
6
)cycloalkoxyalkyl, (C
2
-C
5
)alkenyloxyalkyl, (C
3
-C
6
)alkynyloxyalkyl; X
1
is fluoro; X
2
is halo; X
4
is hydrogen or halo; X
3
is (C
1
-C
4
)alkoxy, (C
3
-C
6
)cycloalkoxy, (C
2
-C
6
)alkenyloxy, (C
3
-C
6
)alkynyloxy, (C
1
-C
4
)alkoxycarbonyl, (C
2
-C
6
)alkenyloxycarbonyl, (C
3
-C
6
)alkynyloxycarbonyl, (C
1
-C
6
)alkylsulfonylamino, (C
1
-C
4
)alkylsulfonylalkylamino, (C
1
-C
4
)alkoxycarbonylmethoxy, or (C
1
-C
3
)alkoxycarbonylethoxy; or when X
1
is fluoro and X
4
is hydrogen, then X
2
and X
3
form a 5- or 6 membered heterocyclic ring fused to the phenyl ring structure to form the bicyclic moiety wherein L is oxygen; R
2
is hydrogen or alkyl; R
3
is alkyl, haloalkyl, alkenyl, alkynyl; alkoxyalkyl; alkenyloxyalkyl; alkynyloxyalkyl; cyanoalkyl; amino, or hydroxy; and R
4
is hydrogen, (C
1
-C
3
)alkyl, or fluorine; and agronomically acceptable salts thereof.
More preferred compounds are compounds of Formula II
wherein: W is oxygen or sulfur; R is (C
1
-C
3
)alkyl, (C
1
-C
3
)haloalkyl, (C
5
-C
6
)cycloalkyl, (C
2
-C
5
)alkenyl, (C
3
-C
6
)alkynyl; R
3
is (C
1
-C
3
)alkyl, (C
1
-C
3
)haloalkyl, (C
2
-C
5
)alkenyl, (C
3
-C
6
)alkynyl, (C
1
-C
3
)alkoxyalky, (C
2
-C
5
)alkenyloxyalkyl, (C
3
-C
6
)alkynyloxyalkyl; cyanoalkyl; and agronomically acceptable salts thereof.
The compounds of Formula I of the present invention can be prepared by the following processes:
Substituted phenylureas (W=O) or thioureas (W=S) are reacted with oxalyl chloride in a solvent inert under the reaction conditions, e.g., chloroform, dichloromethane, carbon tetrachloride, hexane, benzene, toluene, ethyl acetate, DMF, tetrahydrofuran or dioxane to give compounds of Formula I, optionally in the presence of the bases such as Et
3
N, pyridine, NaOH, KOH, Na
2
CO
3
, K
2
CO
3
, NaHCO
3
at a temperature from —40° C. to the boiling point of the solvent for 3 minutes to 48 hours.
Substituted phenylanilines are reacted with isocyanates (W=O) or isothiocyanates (W=S), which are commercially available or can be prepared by known methods, in a solvent inert under the reaction conditions, e.g. chloroform, dichloromethane, carbon tetrachloride, hexane, benzene, toluene, ethyl acetate, DMF, tetrahydrofuran, alcohols, or dioxane to give phenylureas or phenylthioureas,

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