Plant protecting and regulating compositions – Plant growth regulating compositions – Organic active compound containing
Reexamination Certificate
2000-03-03
2002-04-23
Riley, Jezia (Department: 1656)
Plant protecting and regulating compositions
Plant growth regulating compositions
Organic active compound containing
C504S329000, C800S279000, C800S312000
Reexamination Certificate
active
06376430
ABSTRACT:
BACKGROUND OF THE INVENTION
Field of the Invention
The present invention is directed to a method of increasing soybean (determined as well as indeterminate soybeans) yield by the application of a benzoyl urea of Structure (I). Most preferred method is directed to a narrow application window of reproductive indeterminate soybeans in which the application of an insect growth regulator, such as Structure (I), can enhance the seed yield. The increase in yield is likely ubiquitous with other leguminous plants, such as peanuts, lima beans and navy beans, and even cotton. It appears to be a consequence of increased pod numbers on the plant which consequently gives increased seed yield, since the seeds are no smaller in size/weight.
SUMMARY OF THE INVENTION
A method for increasing yield in soybeans by applying, in the absence of insect pressure on the crop, an amount effective for increasing seed pod formation of an active amount of a substituted benzoyl urea represented by structural formula I:
where A is a hydrogen atom, a halogen atom, a methyl group or a methoxy group,
B also represents a hydrogen atom, a halogen atom, a methyl group or a methoxy group, X and Y each represent an oxygen atom or a sulfur atom,
R is a hydrogen atom, an alkyl group, a hydroxy group, an alkoxy group, an alkoxymethyl group, an acyl group or an alkoxycarbonyl group,
R
1
is a hydrogen atom, any molecule or group of molecules containing at least one carbon atom, preferably, an alkyl group unsubstituted or substituted with halogen, with alkoxy, with alkylthio or with cyano, a 1-cycloalkenyl group, a benzyl group unsubstituted or substituted with halogen, a hydroxy group, an alkoxy group, an acyl group, an alkoxycarbonyl group, an alkoxythiocarbonyl group, an alkylsulfonyl group or a phenylsulfonyl group, while furthermore R and R
1
together with the group:
indicated in the above formula may form a ring system, and
R
2
represents a substituted or non-substituted phenyl group or a pyridyl group unsubstituted or substituted with halogen, with nitrocyano or with halogenated alkyl,
wherein said ring system is represented by any of the following formulae:
wherein the formulae Y and R
2
have the aforementioned meanings, alk is a C
1
to C
20
alkyl group and C
1
to C
20
alkylene is a bivalent saturated alkylene group, if R
2
is a substituted phenyl group, the phenyl group contains at least one substituent chosen from the group consisting of:
(a) 1-3 halogen atoms,
(b) 1-2 C
1
to C
20
alkyl groups, unsubstituted or substituted with halogen, hydroxy, C
1
to C
20
alkoxy, C
1
to C
20
alkylthio, C
1
to C
20
dialkyl amino, alkylsulphonyl and phenyl,
(c) tri- or tetramethylene,
(d) a C
1
to C
20
cycloalkyl group, unsubstituted or substituted with halogen or cyano,
(e) 1-2 nitro groups or cyano groups or alkoxy groups,
(f) a dioxymethylene or dioxyethylene group,
(g) an acyl group, unsubstituted or substituted with halogen,
(h) an alkyl sulfonyl, phenyl sulfonyl, alkylthio, phenylthio or phenoxy group, unsubstituted or substituted with halogen,
(i) a sulfonic group, which may alkylated, and
(j) a phenyl group, unsubstituted or substituted with halogen, nitro, cyano, and halogenated alkyl, wherein all alkyl references, unless otherwise noted are C1 to C20.
A more preferred subgenus of structural formula (I) is represented by structural formula (II):
P and Q may be equal or different and each represent a chlorine atom, a fluorine atom or a methyl group,
R
3
represents a hydrogen atom, an alkyl group, a benzyl group, an acyl group or an alkoxycarbonyl group,
R
4
represents from 0-3 substituents selected from the group comprising from 1 to 3 halogen atoms, an alkyl group which contains from 1 to 15 carbon atoms and may be substituted with one or more halogen atoms or with a phenyl group, a cycloalkyl group unsubstituted or substituted with at least one halogen atom a nitro group, a cyano group, a phenyl group, a thiophenyl group, a benzoyl group, a thioalkyl group and an alkylsulfonyl group.
A still more preferred set of substituted benzoyl urea is of the formulae:
where P and Q may be equal or different and each represent a chlorine atom, a fluorine atom or a methyl group,
R
6
is a hydrogen atom or a lower alkyl group and
R
5
represents 1-3 substituents selected from the group comprising 1-3 halogen atoms, an alkyl group which contains from 1 to 15 carbon atoms unsubstituted or substituted with at least one halogen atom, and a cycloalkyl group unsubstituted or substituted with at least one halogen atom, preferably R
5
represents one or two substituents in the position 3 or the position 4 or the positions 3 and 4 of the phenyl group.
Also preferred substituted benzoyl urea of the formulae:
where R
6
is a hydrogen atom or a lower alkyl group, R
7
represents a unsubstituted or substituted phenyl group, R
9
is a hydrogen atom or a methyl group, R
8
represents a phenyl group unsubstituted or substituted with 1-3 halogen atoms, an alkyl group, cyclo-alkyl group, nitro group, tetramethylene group, methylenedioxy group or a methylsulfonyl group.
Preferred benzoyl ureas include:
a substituted benzoyl urea selected from the group consisting of
N-(2,6-dichlorobenzoyl)-N′-(3,4-dichlorophenyl)urea,
N-(2,6-difluorobenzoyl)-N′-(3,4-dichlorophenyl)urea,
N-(2,6-dimethylbenzoyl)-N′-(3,4-dichlorophenyl)urea,
N-(2,6-dichlorobenzoyl)-N′-(4-chlorophenyl)urea,
N-(2,6-dimethylbenzoyl)-N′-(4-chlorophenyl)urea,
N-(2,6-dichlorobenzoyl)-N′-(2,4-dichlorophenyl)urea,
N-(2,6-dichlorobenzoyl)-N′-(4-cyclopropylphenyl)urea,
N-(2,6-dichlorobenzoyl)-N′-(3-chloro-4-iodophenyl)urea,
N-(2,6-dichlorobenzoyl)-N′-(3-chloro-4-bromophenyl)urea,
N-(2,6-dichlorobenzoyl)-N′-(4-isopropylphenyl)urea,
N-(2,6-dichlorobenzoyl)-N′-(3,4-dibromophenyl)urea,
N-(2,6-dichlorobenzoyl)-N′-(4-fluorophenyl)urea,
N-(2,6-dichlorobenzoyl)-N′-(3-trifluoromethylphenyl)urea,
N-(2,6-dichlorobenzoyl)-N′-(4-n-butylphenyl)urea,
N-(2,6-dichlorobenzoyl)-N′-(3-chloro-4-methylsulfonylphenyl)urea,
N-(2,6-dichlorobenzoyl)-N′-(4-t-butylphenyl)urea,
N-(2,6-dichlorobenzoyl)-N′-(3,4-difluorophenyl)urea,
N-(2,6-dichlorobenzoyl)-N′-(2,4-difluorophenyl)urea,
N-(2,6-dichlorobenzoyl)-N′-(4-bromophenyl)urea,
N-(2,6-dichlorobenzoyl)-N′-(2,5-difluoro-4-bromophenyl)urea,
N-(2,6-dichlorobenzoyl)-N′-(4-iodophenyl)urea,
N-(2,6-dichlorobenzoyl)-N′-(3-fluoro-4-chlorophenyl)urea,
N-(2,6-dichlorobenzoyl)-N′-(4-phenylphenyl)urea,
N-(2,6-dichlorobenzoyl)-N′-(4-cyanophenyl)urea,
N-(2,6-dichlorobenzoyl)-N′-(3-fluoro-4-bromophenyl)urea,
N-(2,6-dichlorobenzoyl)-N′-(3-fluoro-4-iodophenyl)urea,
N-(2,6-dichlorobenzoyl)-N′-(2-fluoro-4-iodophenyl)urea,
N-(2,6-dichlorobenzoyl)-N′-(4-n-propylphenyl)urea,
N-(2,6-dichlorobenzoyl)-N′-(4-trifluoromethylphenyl)urea,
N-(2,6-dichlorobenzoyl)-N′-(3-cyclopropylphenyl)urea,
N-(2,6-dichlorobenzoyl)-N′-(2-methyl-4-chlorophenyl)urea,
N-(2,6-dichlorobenzoyl)-N′-(4-sec-butylphenyl)urea,
N-(2,6-dichlorobenzoyl)-N′-(4-iso-butylphenyl)urea,
N-(2,6-dichlorobenzoyl)-N′-(4-ethylphenyl)urea,
N-(2,6-dichlorobenzoyl)-N′-(4-n-dodecylphenyl)urea,
N-(2,6-dichlorobenzoyl)-N′-4-benzylphenyl)urea,
N-(2,6-dibromobenzoyl)-N′-(3,4-dichlorophenyl)urea,
N-(2,6-dichlorobenzoyl)-N′-(methyl)-N′-(3,4-dichlorophenyl)urea,
N-(2,6-dichlorobenzoyl)-N′-(ethyl)-N′-(3,4-dichlorophenyl)urea,
N-(2,6-dichlorobenzoyl)-N′-(methyl)-N′-(4-t-butylphenyl)urea,
N-(2,6-dichlorobenzoyl)-N′-(methyl)-(4-bromophenyl)urea,
N-(2,6-dichlorobenzoyl)-N′-(ethyl)-N′-(4-bromophenyl)urea,
N-(2,6-dichlorobenzoyl)-N′-(ethyl)-N′-(4-isopropylphenyl)urea,
N-(2,6-dichlorobenzoyl)-N′-(ethyl)-N′-(4-n-butylphenyl)urea,
N-(2,6-dichlorobenzoyl)-N′-(methyl)-N′-(4-chlorophenyl)urea,
N-(2,6-dichlorobenzoyl)-N′-(ethyl)-N′-(4-chlorophenyl)urea,
N-(2,6-dichlorobenzoyl)-N′-(ethyl)-N′-(4-t-butylphenyl)urea,
N
Connell John G.
Weiland Robert T.
Reitenbach Daniel
Riley Jezia
Uniroyal Chemical Company, Inc.
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