Note: Descriptions are shown in the official language in which they were submitted.
The invention i.s imldazolinyl benzoic acids, esters
and salts represented by formula (I):
X~
N
(I)
wherein X is hydrogen, alkyl Cl-C3, halogen or nitro; Rl is
alkyl Cl-C4; R2 is alkyl Cl-C6, cycloalkyl C3-C6, alkenyl
C2-C4, phenyl, halophenyl or benzyl or when Rl and R2 a.re
taken together with the carbon to which they are attached
they may represent cycloalkyl C3-C6 optionally substituted
with methyl; R3 is hydrogen, alkyl Cl-C12 optionally substi-
tuted with one Cl-C3 alkoxy group or one C3-C6 cycloalkyl
group or one phenyl group or one furyl group, alkenyl
C3-C5 optionally substituted with one or two Cl-C3 alkyl
group(s) or one phenyl group or with one to two halogen sub-
stituent(s), alkynyl C3-C5 optionally substituted with one
or two Cl-C3 alkyl group(s) or one phenyl group or with
one to two halogen substituent(s) bcnzyl, cyclohexenylmethyl,
ethynylcyclohexyl, ethynylalkyl, pentadienyl or cycloalkyl
C3-C6 optionally substituted with one or two Cl-C3 alkyl
group(s); or a salt forming cation of alkali metals, ammon-
ium and aliphatic ammonium; and when Rl and R2 are no~ the
same the optical isomers; and the isomeric and tautomeric
mixtures thereof; and except when R3 is a salt-forming
cation, the acid addition salts thereof.
- 1 -
.................... ;~
9'87~
The invention also relates to a method for control-
ling undesirable plant species with imidazolinyl benzoates
comprising applying to the foliage of the undesirable plant
species or to soil containing seeds, seedlings, or propagat-
ing organs of the undesirable plant species, a herbicidally
effective amount of an imidazolinyl benzoate compound depict-
ed by formula I above.
The invention further relates to a method for the
preparation of the formula I imidazolinyl benzoates.
Preferred compounds for use as herbicidal agents
are those represented by formula I above, wherein X is hydro-
gen, alkyl Cl-C3 or halogen; Rl is alkyl Cl-C3; R2 is a]kyl
Cl-C3 or cyclohexyl, and when Rl and R2 are taken together
with the carbon to which they are attached they represent
cyclohexyl or methylcyclohexyl; R3 is hydrogen, alkyl Cl-C
optionally substituted with one Cl-C3 alkoxy group or one
C3-C6 cycloalkyl group or one phenyl group or one furyl group
or with one to three halogen substituent(s) preferably chlor-
ine, alkenyl C3-C5 optionally substituted with one or two
Cl-C3 alkyl group(s) or one phenyl group or with one to two
halogen substituent(s) preferably chlorine, alkynyl C3-C5
optionally substituted with one or two Cl-C3 alkyl group(s)
or one phenyl group or with one to two halogen substituent(s)
preferably chlorine, benzyl, cyclohexenylmethyl, ethynylcyclo-
hexyl, ethynylalkyl, pentadienyl or cycloalkyl C3-C6 option-
ally substituted with one or two Cl-C3 alkyl group(s); or a
salt forming cation of alkali metals and ammonium; and when
Rl and R2 are not the same the optical isomers; and the iso-
meric and tautomeric mixtures thereof; and except when R3 is
a salt-forming cation, the acid addition salts thereof.
Still more preferred formula (I) compounds are
those wherein Rl is methyl; R2 is isopropyl; and the compounds
may be grouped as follows:
a. wherein X is hydrogen or chlorine; R3 is hydrogen; the
alkali metal and ammonium salts thereof; the optical isomers
thereof; and the isomeric and tautomeric mixtures thereof;
b. wherein X is hydrogen, methyl or chlorine; R3 is alkyl
Cl~C12 optionally substituted with one Cl-C3 alkoxy group
or one C3-C6 cycloalkyl group or one phenyl group or one furyl
group or with one to three halogen substituent~s) preferably
chlorine; the optical isomers thereof; and the isomeric and
tautomeric mixtures thereof; and the acid addition salts
thereof;
c. wherein X is hydrogen, methyl or chlorine; R3 is alkenyl
C3-C5 optionally substituted with one or two Cl-C3 alkyl
group(s) or one phenyl group or with one to two halogen sub-
stituent(s) preferably chlorine; the optical isomers thereof;
and the isomeric and tautomeric mixtures thereof; and the acid
addition salts thereof;
d. wherein X is hydrogen., methyl or chlorine; R3 is alkynyl
C3-C5 optionally substituted with one or two Cl-C3 alkyl
group(s) or one phenyl group or with one to two halogen sub-
stituent(s) preferably chlorine; the optical isomers thereof;
and the isomeric and tautomeric mixtures thereof; and the acid
addition salts thereof.
In accordance witn this invention, formula I imid-
azolinyl ben~oates wherein R3 is not H can be prepared by re-
acting an imidazoisoindoledione represented by formula II
- with an appropriate alkali metal alkoxide. The reaction is
preferably conducted under a blanket of inert gas at a temp-
erature between 20 C. and 50 C. Generally, an alkali metal
-- 3 --
~9~7~
or a]kali m~tal hydride is mixed with an appropriate alcohol and
the mixture then admixed with the imidazoisoindoledione IT. I'ref-
erab]y the ratio of alcohol to imidazoisoindoledione is from 1.1
to 1.0 to 5.0 to 1Ø
Among the inert gases which may be used to blanket these
reactions are nitrogen~ argon and helium; but nitrogen is preferred.
Alkali nmetals and alkali metal hydrides which may be used
include sodium, sodium hydride, potassium, potassium hydride, lith-
ium and lithium hydride.
These reactions may be graphically illustrated as follows:
X ~ ~ ~ R30- ~ COOR3
(II) (III) (I) 0
wherein X, Rl, R2 and R3 are as described above.
In these reactions, the alcohol functions as both
reactant and solvent. As such, a secondary solvent is not
required; however, when an expensive alcohol is used in the
reaction and/or a large excess of alcohol would normally be
required to provide optimum reaction conditions, it may be
desirable to add a less expensive secondary solvent such as
dioxane, tetrahydrofuran or other non-protic solvent, to the
reaction mixture. The amount of non-protic solvent added
to the reaction mixture may be widely varied in this use;
however, it generally will not exceed fourfold the amount
of alcohol used. Thus, the ratio of secondary solvent to al-
cohol, which may be employed in the process of the present
..
.~ ~ .. .. .
9~37B
1 invention, is from 0.0:1 to 4.0:1.
Formula I compounds, wherein R3 is hydrogen are
prepared by reacting a formula II imidazoisoindoledione with
an excess of hydrochloric acid in the presence of a water-
miscible solvent such as tetrahydrofuran or dioxane. Thisreaction yields the formula IV lactone hydrochloride which,
when treated with one equivalent of base such as sodium hy-
droxide, potassium hydroxide or sodium carbonate, yields the
corresponding acid. This reaction can be illustrated as fol-
lows:
lS ~ 1 X ~ I 1; UCl
(II) o (IV)
~Rl ~!!~!~1
(I)
The thus-formed imidazolinyl acid can then be con-
verted to the corresponding alkali metal, ammonium or ali-
phatic ammonium salt.
Where the alkali metal salt is desired, the acid
is treated with a concentrated aqueous solution of the alkali
metal hydroxide, followed by removal of the water, preferably
through azeotropic distillation with an organic solvent such
as dioxane.
11~'~
1 The ammonium or aliphatic ammonium salts prepared
in similar fashion excepting that the formula I acid is par-
tially dissolved in a lower alcohol such as methanol, etha-
nol, isopropanol, or the like, and the thus-formed solution
treated with ammonia or the appropriate aliphatic amine.
Thereafter, the reaction mixture is concentrated and the re-
maining solid treated with hexane and then dried to recover
the ammonium or aliphatic ammonium formula I salt.
The term, "aliphatic ammonium," means an aliphatic
ammonium group of monoalkylammonium, dialkylammonium, tri-
alkylammonium, monoalkenylammonium, dialkenylammonium, tri-
alkenylammonium, monoalkynylammonium, dialkynylammonium,
trialkynylammonium, monoalkanolammonium, dialkanolammonium,
or trialkanolammonium, and the aliphatic ammonium group con-
taining from 1 to 18 carbon atoms.
The aliphatic ammonium salts of the compounds ofthe invention are prepared from organic amines having a
molecular weight below about 300. ~hese amines include meth-
ylamine, ethylamine, n-propylamine, isopropylamine, n-butyl-
amine, isobutylamine, sec-butylamine, n-amylamine, iso-amyl-
amine, hexylamine, heptylamine, octylamine, nonylamine, decyl-
amine, undecylamine, dodecylamine, tridecylamine, tetradecyl-
amine, pentadecylamine, hexadecylamine, heptadecylamine,
octadecylamine, methylethylamine, methylisopropylamine,
methylhexylamine, methylnonylamine, methylpentadecylamine,
methyloctadecylamine, ethylbutylamine, ethylheptylamine,
ethyloctylamine, hexylheptylamine, hexyloctylamine, dimethyl-
amine, diethylamine, di-n-propylamine, diisopropylamine,
di-n-amylamine~ diisoamylamine, dihexylamine, diheptylamine,
dioctylamine, trimethylamine, triethylamine, tri-_-propyl-
1~99t378
1 amine, triisopropylamine, tri-n-butylamine, triisobutylamine,
tri-sec-butylamine, tri-n-amylamine, ethanolamine, n-prop-
anolamine, isopropanolamine, diethanolamine, N,N-diethyleth-
anolamine, N-ethylpropanolamine, N-butylethanolamine, allyl-
amine, n-butenyl-2-amine, n-pentenyl-2-amine, 2,3-dimethyl-
butenyl-2-amine, di-butenyl-2-amine, _-hexenyl-2-amine and
propylenediamine.
The compounds represented by formula (I) above may
be mixtures of two position isomers when X is other than hy-
drogen, since the intermediate imidazoisoindolediones of form-
ula (II) are also mixtures of isomers when X is not hydrogen.
As shown below, the compounds of formula (II) may be prepared
from the corresponding phthalimidocarboxamide precursors by
cyclizing same, and that cyclization occurs at either imide
carbonyl group giving rise to an isomeric mixture when X is
other than hydrogen:
N- C - CONH2 ~ R2
X R2 OH or H X~N ~O
and
~Rl
X R2
wherein Rl, R2 and X are as defined above, excepting that X
; cannot be hydrogen.
It should also be understood that the imidazolinyl
benzoates represented by formula I above, may be tautomeric.
'' ..
-- 7 --
78
1 While, for convenience, they are depicted by a single struc-
ture identified as formula I, they may exist in either of the
isomeric forms illustrated as follows:
x ~ (~13 X ~ COOR3
R1 or ~ R
O HN O
wherein X, Rl, R2 and R3 are as described. As such, both
isomeric forms of the imidazolinyl benzoates are meant to
be included under the formula I definition.
These compounds are amphoteric. They will dissolve
in both acidic and basic aqueous solutions and when treated
with strong acids, particularly strong mineral acids such as
hydrochloric acid, sulfuric acid or hydrobromic acid, will
form the acid addition salts of the imidazolinyl benzoates
I.
It should also be understood that when Rl and R2
represent different groups on the irnidazolinyl benzoates,
depicted b~ formula ~, the carbon atom to which they are
attached is an asymmetric carbon atom. Therefore, the prod-
ucts (as well as their intermediates) exist in d- and 1-
forms as well as dl- forms.
Preparation of the d- or the 1- form is thus read-
ily obtained by reacting the appropriate optically actived- or l-imidazoisoindoledione II with the appropriate alcohol
III to obtain the corresponding d- or l-imidazolinyl benzo-
ate I.
The formula II imidazoisoindolediones II which are
used as intermediates for the preparation of the imidazo-
.
?871~
1 linyl benzoates of this invention are described i.n our
United States Patent No. 4,017,510, issued April 12, 1977.
The invention includes imidazolinyl benzamides hav-
ing the structure:
~ CON~
~ Rl
N O
wherein Rl is alkyl Cl-C4; R2 is alkyl Cl-C6, cycloalkyl
C3-C6, alkenyl C2-C4, phenyl, halophenyl or benzyl; and
when Rl and R2 are taken together with the carbon to which
they are attached they may form cycloalkyl C3-C6 optionally
substituted with methyl; R3 and R4 each individually repre-
sent hydrogen, alkyl Cl-C~, alkenyl C3-C5, alkynyl C3-C5,
or benzyl; and when Rl and R2 represent different substit-
uents, the optical isomers thereof.
While the imidazolinyl benzamides of ~his invention
are illustrated by the structure identified as formula (III)
above, it should be understood that these compounds may be
tautomeric. As such, they could have the structure:
~ CON ~ 3
~R2
HN O
wherein Rl, R2, R3 and R4 are as described. Both tautomeric
forms are, of course, intended to be included as compounds
of the invention when reference is made throughout the
specification and claims to the formula III structure.
In accordance with the invention, imidazolinyl benz-
8~8
1 amides having the structure:
~ ~ R
~ I ~ R
N O
wherein Rl, R2, R3 and R4 are as described above, can be
prepared by reacting an imidazoisoindoledione having the
structure:
1 V
where Rl and R2 are as described above, with an amine repre-
sented by the formula: R4R3NH (IV) where R3 and R4 are as
described above.
The mole ratio of amine (IV) to imidazoisoindole-
dione (V) should be in the range of 1:1 to 10:1, and prefer-
ably 2:1 to 5:1. The reaction is preferably conducted in a
: non-protic solvent such as tetrahydrofuran, dioxane, toluene,
xylene, benzene, or the like, at a temperature between 50C.
and 100C.
It should also be understood that when Rl and R2
represent different substituents, the carbon to which Rl and
R2 are attached is an asymmetric center and the products
(as well as their intermediates) exist in d- and 1- forms as
well as dl- forms. Further, when the imidazoisoindoledione
(V) is optically active and either the d- or 1 isomer is re-
acted with the formula (IV) amine, R4R3NH, the corresponding
-- 10 --
d- or l-imidazolinyl benzamide (III) is for.med.
The intermediate imidazoisoindoledione (V), which
are essential to the preparation of the formula (III) imid-
. azolinyl benzamides of the present invention, are described
.
.:- with a method for their preparation in our copending Serial
No. 268,327.
The method for the preparation of the compounds
of the invention may be graphically illustrated as follows:
, R3
N ~ + R4R3N11 ~ ~ ~1
~ ~Rl ~Rl
wherein Rl, R2, R3 and R4 are as described above.
Illustrative of the compounds of this invention
are:
o-(5-isopropyl-5-methyl-4-oxo-2-imidazolin-2-yl)-
3-butynylbenzamide;
;. o-(5,5-diethyl-4-oxo-2-imidazolin-2-yl)-N,N-diethyl-
: benzamide;
o-(5-isopropyl-5-methyl-4-oxo-2-imidazolin-2-yl)-
N-2-butenylbenzamide;
o-(5-isopropyl-5-methyl-4-oxo-2-imidazolin-2-yl)-
~ 20 N-methylbenzamide;
.~ o-(5-isopropyl-5-methyl-4-oxo-2-imidazolin-2-yl)-
N-isopropylbenzamide;
o-(5-isopropyl-5-methyl-4-oxo-2-imidazolin-2-yl)-
.~ N-allylbenzamide;
-~ o-(5-isopropyl-5-methyl-4-oxo-2-imidazolin-2-yl)-
~ j - 11 -
.~
8'7B
1 N,N-diallylbenzamide;
o-(5-isopropyl-S-methyl-4-oxo-2-imidazolin-2-yl)-
N-l,l-dimethyl-2-propynylbenzamide;
o-(5-n-propyl-5-methyl-4-oxo-2-imidazolin-2-yl)-
N-1,1-dimethylallylbenzamide;
o-(5-isopropyl-5-methyl-4-oxo-2-imidazolin-2-yl)-
N,N-diphenylbenzamide;
o-(5-cyclohexyl-5-methyl-4-oxo-2-imidazolin-2-yl)-
N-2-propynylbenzamide;
_-(5-benzyl-5-methyl-4-oxo-2-imidazolin-2-yl)-
N,N-diisopropylbenzamide;
o-(5-isopropyl-5-methyl-4-oxo-2 imidazolin-2-yl)-
N-benzylbenzamide; and
o-(4-oxo-1,3-diazospiro[4,5]dec-2-en-2-yl)-N-n-
propylbenzamide.
Preferred compounds of the invention have the
structure of formula III above, wherein Rl is methyl; R2 is
alkyl Cl-C3, preferably isopropyl, cyclohexyl or benzyl, or
when Rl and R2 are taken together with the carbon to which
they are attached they may represent cyclohexyl; R3 and R4
each individually represent hydrogen, alkyl Cl-C3, allyl,
dimethylallyl, propynyl, or benzyl; and when Rl and R2 are
different, the optical isomers thereof.
The compounds of this invention are highly effec-
tive herbicidal agents useful for the control of both mono-
cotyledonous, sedge (cyperaceous) and dicotyledonous plants.
They may be employed for the postemergence control of unde-
sirable plant species by applying a herbicidally effective
amount thereof to the foliage of the plants, or they may be
used for the preemergence control of the undesirable plants
- 12 -
1 by applylng a herbicidally effective amount of the active
compound to soil containing seeds, seedlings or propagating
organs, of the undesirable plants. Since the imidazolinyl
benzoates (I) of the present invention exhibit very limited
solubility in water, they are generally formulated as wett-
able powders, emulsifiable concentrates, or flowable liquids
which are usually dispersed in water or other inexpensive
liquid diluent for application as a liquid spray. The com-
pounds of the invention may also be prepared as granular
formulations containing, generally, about 10% to 15~ by
weight of toxicant.
Typically, a wettable powder can be prepared by
grinding together about 25% to 80% by weight of the imidazo~
linyl benzoate, about 2% to 5~ by weight of a surfactant such
as sodium N-methyl-N-oleoyl taurate, alkyl phenoxy polyoxy-
ethylene ethanol, or sodium alkyl naphthalene sulfonate, 5%
to 10% by weight of a dispersing agent such as a highly puri-
fied sodium lignosulfonate and 25% to 63% by weight of a fine-
ly divided carrier such as kaolin, attapulgite, diatomaceous
earth, or the like.
A typical formulation prepared in accordance with
the above description is as follows:
50~ by weight of 2-propynyl o-(5-isopropyl-5-methyl-
4-oxo-2-imidazolin-2-yl) benzoate, 3% by weight of sodium
; 25 N-methyl-N-oleoyl taurate, 10% by weight of sodium lignosul-
fonate, and 37% by weight of kaolin.
Flowable liquid formulations can be prepared by
grinding together about 40% to 60% by weight of the formula
I imidazolinyl benzoate, 2~ to 3% by weight of the sodium
salt of condensed naphthalene sulfonic acid, 2% to 3~ by
- 13 -
1 weight of a ge]ling clay, 2~ by weight cf propylene glycol,
and from 54~ to 32~ by weight of water~
A typical granular formulation can be prepared by
dissolving or dispersing the active compound in a solvent
and applying the toxicant to a sorptive or non-sorptive car-
rier such as attapulgite, corn cob grits, pumice, talc, or
the like.
As indicated above, the imidazolinyl compounds,
depicted by formula I, are effective preQmergence herbicides.
They are highly effective for the control of broadleaf weeds
and grass plants when applied at a rate of from about 0.07
kg per hectare to 11.2 kg per hectare to soil containing
seeds, seedlings or propagating organs of ~he broadleaf
weeds, sedges, or grass plants.
The compounds of the invention are also effective
for the control of broadleaf weeds, sedges, and grass plants
when applied at the rate of from about 0.28 kg per hectare
to 11.2 kg per hectare to the foliage of the plants~
While the compounds of this invention are very ef-
fective for controlling a wide variety of plant species,they are unique among herbicides in their ability to control
certain cyperaceous plants, particularly sedges, at relative-
ly low rates of application. In practice, the formula I com-
pounds have been found to be most effective as sedge control
agents when applied as a preemergence application at rates
of from 0.14 kg per hectare to 11.2 kg per hectare. It is,
of course, recognized that higher rates of application of
the formula I compounds can be used for sedge and other per-
ennial plant control when infestations of the cyperacae or
perennial plants are especially heavy. Under such condi-
- 14 -
~t~
1 tions, the formula I imidazolinyl benzoates may be applied,
preemergence or postemergence, at rates as high as 25 kg
per hectare.
Among the cyperacae which can be controlled with
the imidazolinyl benzoates of this invention are purple nut-
sedge (Cyperus rotundus L.), yellow nutsedge (Cyperus
esulentus L.), false nutsedge (Cyperus strigosus) and the
flat sedges, umbrella plants and kyllinga.
This invention is further illustrated by the fol-
lowing examples:
EXAMPLE 1
Preparation of 2-Propynyl o-(5-isopropyl-5-methyl-4-oxo-
_. _
2-imidazolin-2-yl benzoate.
To 12.5 ml o propargyl alcohol is added 0.1 g
of a 50% suspension of æodium hydride in mineral oil. The
addition is made under a blanket of nitrogen while the mix-
ture is stirred and the temperature thereof maintained at
from 20C. to 25C. by means of external cooling. The for-
mation of the sodium salt of propargyl alcohol is complete
in about 1 to 2 hours. To this solution is added 5.0 g of
3-isopropyl-3-methyl-5H-imidazo[2,1-a]isoindole-2(3H),5-dione
and the mixture stirred at room temperature overnight under
a blanket of nitrogen. Thin layer chromatography indicates
incomplete reaction and an additional 50 mg of a 50% suspen-
sion of sodium hydride in oil is added to the reaction mix-
ture. After stirring overnight, the mixture is cooled to 5C.
and 0.7 ml of 3N hydrochloric acid is added. The mixture
is then diluted with methylene chloride, washed with water
and the organic phase dried and concentrated in vacuo. The
crystalline residue is transferred to a filter funnel with
- 15 -
1 hexane and air dried to give 6.02 g of 2-propynyl o~(5-iso-
propyl-5-methyl-4-oxo-2-imidazolin-2-yl)benzoate, melting
point 131-144C. Material from a similar reaction was re-
crystallized from acetone-hexane to give pure product melting
point 145-147C.
EXAMPLE 2
Preparation of Formula I Imidazolinyl Benzoates.
The following imidazolinyl benzoates were prepared
by essentially the same procedure as that described in Ex-
ample 1, but substituting the appropriate alcohol for pro-
pargyl alcohol and the appropriate imidazoisoindoledione for
3-isopropyl-3-methyl-SH-imidazo[2,1-a]isoindole-2(3H),
5-dione. Graphically, the reaction may be illustrated as
follows:
- 16 -
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c~ ~ ~
o c~ ^ ^ c) c~
~-1 ~ J
O ~-- ~J ~I rl ~ N~I J
--i N P~ U`~ ~ ~ ~ NI N
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Y . ~ N r~ ~1~I C~
~ ~1 1 1 1 ~
(Y- / ~ I O t~ lS~ I ~ ~1 ~1 ~1
; ~-J o ~I t~
O \ O ~ I O
O \-- ~ ~
>=<
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__ ~__
X ~) ~ ~ N t ) C~
1~ ~ ~ ~ 11 Il ~ N t~)
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N ~ N
~ r~) ~: ~ N ^ ~ ~ c~
Z. PC C~ N N ^ C~
N 5~ ~ N N I ~ ~ `~
~ ~ X t~ X C~ C~
0~ ~ C~
I . I I
+
O P~ _ - .
N
~ _ ~. N N N N N N N N N N 01
Z ~ ~ ~ r~
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\ ~ ~ : ~ C~ V V C~ ~ V
:~ X
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~: C~ )
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-- 18 --
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1 EXAMPLE 3
Preparation of l,l-Dimethylallyl o-(5-isopropyl~S-methyl-
_
4-oxo-2-imidazolin-2-yl)benzoate hydrochloride.
COOC(C~3)2CH CH2 ~ Cooc(cH3)2cH CH2
N~CH(CH3)2 ~ICl ~NL~cH(cH3)2
To a solution containing 164 mg. l,l-dimethylallyl
o-(5-isopropyl-5-methyl-4-oxo-2-imidazolin-2-yl)benzoate
(0.5 mmol~ in 5 ml methylene chloride and 5 ml absolute eth-
anol is added 0.5 ml l.ON hydrochloric acid. The mixture is
concentrated ln 'vacuo and the residue treated with ether to
give a crystalline product which is removed by filtration,
washed with ether and air dried to give 170 mg hydrochloride
salt, melting point 259-262C. (decomp.~. The melting point
of this and other salts is dependent upon the rate of heat-
ing.
EXAMPLE 4
Preparation of o-(5-Isopropyl-5-me*hyl-4-oxo-2-imidazolin-
~2-yl)be'n'z'oic ac'id.
O
~ ~ ~ ~ ~ ~ HCl
O A
' ~ COOH
NaOH ~ ~
N O
'
- 25 -
9878
1 To a stirred solution containing 5 g of 3-isopropyl-
3-methyl-SH-imidazo[2,1-a]isoindole-2(3H),5-dione in 15 ml
dioxane is added a mixture of 10 ml concentrated hydrochloric
and 10 ml water. The mixture is heated to the boiling point
and then allowed to cool to room temperature. The crystal-
line solid is removed by filtration, washed with water, ace-
tone and air dried. The filtrate is concentrated ln vacuo,
the solid washed with acetone and air-dried. Thus, in two
crops, a total of 4.5 g o~ the lactone hydrochloride, repre-
sented by structure A, is obtained, melting point 265C.(decomp.).
To a stirred, partial solution of the hydrochloride
salt (4.5 g) in 30 ml water is added a solution containing
0.6 g sodium hydroxide in 10 ml water. Complete solution
occurs in a few minutes, and after approximately 15 minutes
a solid separates from the solution. Thi~ is removed by fil-
tration. The filtrate is concentrated ln vacuo, the solid
removed by filtration, combined with the ~irst solid, washed
with water and air-dried to give 3.8 g of o-15-isopropyl-5-
methyl-4-oxo-2-imidazolin-2-yl)benzoic acid, melting point
162-163C. The analytically pure sample had melting point
163-165C.
EXAMPLE S
Salts of o-(5-Isopropyl-5-methyl-4-oxo-2-imidazolin-2-yl)-
..
benzoic acid.
,
The sodium salt is prepared by adding with stirring
9.9 ml lN sodium hydroxide to a partial solution of 2.58 g
imidaæolinyl acid in ~0 ml water. After 1.5 hours, the solu-
tion is concentrated in vacuo and the remaining water then
removed azeotropically with dioxane to give the hydroscopic
- 26 -
1 sodium salt, melting point 184-188C.
Amine salts are simply made in methanol. Thus,
to a stirred, partial solution of 5.0 g imidazolinyl acid
in 15 ml methanol is added 3.17 ml triethylamine. After 0.75
hour, a cleax solution is obtained. The solution is concen-
trated and the residual slurry diluted with hexane, filtered
and dried to give the triethylamine salt, melting point 54~
-55C. The isopropylamine salt prepared similarly has melt-
ing point 92-98C.
EXAMPLE 6
Preparation of o-(5-Isojpropyl-5-methyl-4-oxo-2-imidazolin-
2-yl)-N,N-dimethylbenzamide.
To a cold solution of 180 g of 3-isopropyl-3-methyl-
5H-imidazo[2,1-a]isoindole-2(3H),5-dione in 300 ml of dry tet-
rahydrofuran in a pressure bottle is added 68 g of dimethyl-
amine. The bottle is sealed and the mixture heated to 50C.
with stirring for 16 hours. The mixture is cooled, and the
contents of the bottle transferred to a flask. The solvent
is then removed ln vacuo~ The crystalline residue is then
suspended in ether, filtered, washed with ether, and air-
-dried to give 195 g of o-tS-isopropyl-5-methyl-4-oxo-2-
-imidazolin-2-yl)-N,N-dimethylbenzamide, melting point 144-
-146C. This product is recrystallized from acetonitrile to
give an analytically pure product, melting point 147-150C.
EXAMPLE 7
Preparation of Formula I Im d_zolinyl benzamides.
Using essentially the same procedure as that des-
; cribed in Example 6, but substituting the appropriate imid-
azo[2,1-a]isoindole-2~3H),5-dione and the appropriate amine
for dimethylamine, yields the compounds set forth below.
~ 27 -
-
1 ~ CON~ 3
: ~ ~ Rl
N O
. __ _ __. __ .
Rl R2 R3 R4 Melt ng
. _ . . _.
-(CH2)5- H H 211-212
_ _ _ _.
CH3 CH(Ctl3)2 ~ 174-175
CH3 C~(CH3)2 H CH3 203-204 .
. ,
-(CH2)5- CH3 CH3189-190.5
-(CH2)5- H CH3 259-261
l ~ _
CH3 ¦ CH(CH3)2 H -CH2C-CH 202-205
EXAMPLE 8
Postemergence Herbicidal Activity.
The postemergence herbicidal activity of the com-
pounds of the invention is demonstrated by the following
tests, wherein a variety of monocotyledonous, cyperaceous
and dicotyledonous plants are treated with test compounds
dispersed in aqueous acetone mixtures. In the tests, seed-
ling plants are grown in separate cups for about 2 weeks.
The test compounds are dispersed in 50/50 acetone/water mix-
tures containing 0.5~ TWEEN~ 20, a polyoxyethylene sorbitan
monolaurate surfactant of Atlas Chemical Industries, in suf-
ficient quantity to provide the equivalent of about 0.07 kg
to 11.2 kg per hectare of active compound when applied to
- 28 -
~l~g~
l the plants through a spxay nozzle operatlng at 2. 8 kg/Cu
pressure for a predetermined time. After spraying, the
plants are placed on greenhouse benches and are cared for
in the usual manner, commensurate with conventional green-
house practices. Two weeks after treatment, the seedlingplants, with the exception of wild oats which are rated at
5 weeks, are examined and rated according to the rating sys-
tem provided below. The data obtained are reported in
Table I and II below.
% Difference i.n Growth
Rating System: from the Check*
0 - No effect 0
1 - Possible effect l - 10
2 - Slight effect 11 - 25
3 - Moderate effect 26 - 40
5 - Definite injury 41 - 60
6 - Herbicidal effect 61 - 75
7 - Good herbicidal effect 76 - 90
8 - Approaching complete kill 91 - 99
9 - Complete kill 100
4 - Abnormal growth; that is, a definite physiological
malformation but with an over-all effect less than
a 5 on the rating scale.
*Based on visual determination of stand, size, vigor,
chlorosis, growth malformation and over-all plant
appearance.
Plant abbreviations:
PN - Purple Nutsedge (Cyperus rotundus L.
SE - Sesbania (Sesbania exaltata)
MU - Mustard (Brassica kaber)
PI - Pigweed (Amaranthus retroflexus)
RW - Ragweed (Ambrosia artemisiifolia
- 29 -
~i~g87~
1 MG - Morningglory (Ipomoea purpurea)
BA - Barnyardgrass (Echinochloa crusgalli)
CR - Crabgrass (Digitaria sanguinalis)
,
FO - Green Foxtail (Setaria viridis
WO - Wild Oats (Avena fatua)
TW - Teaweed (Sida spinosa)
VL - Velvetleaf (Abutilon theophrasti)
CN - Corn (Zea mays)
CO - Cotton (Gossypium hirsutum)
SY - Soybean (Glycine max)
RI - Rice (Oryza sativa)
JW - Jimsonweed (Datura stramonium L.)
- 30 -
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1 EXAMæLE 9
Preemer~ence Herbicidal Activity.
The preemergence herbicidal activity of the com-
pounds of the present invention is exemplified by the follow-
ing tests in which the seeds or propagating organs of a var-
iety of monocotyledonous, cyperaceous and dicotyledonous
plants are separately mixed with potting soil and planted on
top of approximately 2.5 cu of soil in separate (size) cups.
After planting, the cups are sprayed with the selected aque-
ous acetone solution containing test compound in sufficientquantity to provide the equivalent of about 0.28 kg to 11.2
kg per hectare of test compound per cup. The treated cups
are then placed on greenhouse benches, watered and cared for
in accordance with conventional greenhouse procedures.
Three or four weeks after treatment, the tests are termi-
nated and each cup is examined and rated according to the
rating system set forth in Example 8. The herbicidal pro-
ficiency of the active ingredients of the present invention
is evident from the test results which are repsrted in
Tables III and IV below.
- 47 -
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-- 64 --
1 EXAMPLE 10
Selective Postemergence Herbicidal Activity.
The selective postemergence herbicidal activity
of the compounds of the invention is demonstrated by the fol-
lowing tests, wherein sorghum [Sorghum bicolor (L) Woeuch],spring wheat (Triticum acstlvum, cv. Auza) and barley
(Hordcum vulgare, cv. Steptoe) plants are treated with test
compounds dispersed in aqueous acetone mixtures. In these
tests, the procedure described in Example 8 is followed, and
the treated plants are examined and rated according to the
rating system set forth in Example 8.
The data obtained are reported in Table V below~
. ,
- 65 -
o ~-- -
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-- 66 --
11~9~ B
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- 67 -
1~0~
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-- 68 --
987B
1 EXAMPLE 11
Selective Preemergence Herbicidal Activity
By the procedure described in Example 9, the se-
~: lective preemergence herbicidal activity of the compounds
of the invention is evaluated using sorghum [Sorghum bicolor
(L) Moeuch], spring wheat (Triticum acstivum, cv. Auza) and
barley (Hordeum vulgare, cv. Steptoe). At termination the
tests are rated according to the rating system set forth in
Example 8.
The data obtained are reported in Table VI below~
.':~. .
- 69 -
~1~98~78
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-- 70 --
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-- 72 --
