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Патент USA US3097097

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3,097,088
Patented July 9, 1963
2
' and higher temperatures are operable and none of the
reaction conditions are critical in any way.
3,097,088
Suitable oils for herbicidal use include both toxic and
OIL-SOLUBLE PLANT GROWTH REGULATION
AGENTS
non-toxic oils. These oils can be derived from crude
petroleum or from animal or vegetable sources.
Richard A. Reck, Hiusdale, Walter W. Abramitis,
Downers Grove, and Charles S. Wilhclmy, Chicago,
111.; said Reck assignor, by mesne assignments, to Ar
Such
oils include tall oils, kerosene, light ‘and heavy lubricating
oils and benzine. Where the solution is to be used for de
m'our and Company, a corporation of Delaware
foliation or rooting purposes, it is preferable to use a non
No Drawing. Filed June 15, 1959, Ser. No. 820,081
9 Claims. (Cl. 7l—2.5)
toxic oil which is relatively harmless to the plant. We
10 prefer to use relatively non-volatile oils, particularly
petroleum fractions, to obtain maximum bene?t from
the growth regulatory amine salts.
Our invention relates to plant response agents and more
particularly to oil-soluble, 3,6-endoxohydrophtha1ic acid
The oil solutions are applied to the plants by spraying I
or
painting and the plant can even be dipped in the solu
Salts containing a 3,6-endoxohydropht-halic acid radical
have been utilized in plant growth regulation previously. 15 tion. We prefer spray application when large areas are
to be treated.
The maximum utilization of these salts has been ham
amine salts.
'
The amount of 3,6-endoxohydrophthalic acid-amine
pered by two phenomena. First, the water and oil solu
bility of the hydrocarbon-containing ‘salts decrease as the
number of carbon atoms in the hydrocarbon chain in
salt in solution to be applied to a particular plant varies
with the species of the plant and with the desired result.
vFor
example, good leaf abiscission is obtained in young
20
creases. Secondly, aqueous salt solutions are relatively
bean
plants when the plants are sprayed with a 0.1%
ineffective as plant growth regulators when applied to
salt solution and leaf abscission is obtained in young
plants in arid regions and in regions where there is
American Holly bushes with a 1% spray. On the other
excessive rainfall. .It appears that the presence of a
hand,
an oil solution containing 25%, or more, of the
solvent is necessary if the henahydrophthalic acid salt is
to pass into the plant. In arid regions, the water evapo 25 desired amine salt is needed to kill trees when introduced
into the tree through bore holes in the roots or trunk.
rates before effective amounts of the salt can pass into the
The following examples more fully illustrate our in
plant and, as a result, the salts are ineffective. In regions
vention but it is not intended that the scope of our in
of excessive rainfall, the salts wash off the plant and
vention be limited by the amines used, the reaction con
leach {from the top soil at ‘a rate such that the use of these
ditions, or endoxohydrophthalic acids utilized. Rather it
salts is economically impossible.
is intended that all equivalents obvious to those skilled
We have now discovered oil-soluble amine salts con
in the ‘art be included within the scope of our invention
taining 3,6-endoxohydrophthalic acid radicals, which ex
as
claimed.
pand consider-ably the ‘armamentarium of the ento
Example I
mologist. These oil-soluble salts are formed when 3,6
endoxohydrophthalic acids or anhydrides are reacted with 35
To prepare the lO-aminononyldecane salt of 3,6-en
primary amines having the primary amine substituent at
doxohexahydrophthailic acid, 28.3 grams of IO-aminonon
tached to a secondary or tertiary carbon atom. Prefer
yldecane was added to 9.6 grams of ?nely ground 96%
ably, these amines contain ‘from about 8 to about 18 car
3,6-endoxohydrophth'alic acid. The mixture was warmed
bon atoms in at least one of the onganic radicals at
on a steam bath to about 70~75° C. with stirring until a
tached to the amine substituted carbon atom and optimal
ly from about 8 to about 14 carbon atoms. I prefer to
use aliphatic amines having the primary amine substitu
homogeneous reaction mixture was formed. The result
ing colorless liquid salt had a neutralization equivalent of
398 (theory 376) and was 94.4% pure.
ent attached to a secondary carbon atom.
Amines utilized in preparing the 3,6-endoxohydro 45
phathalic acid salts of our invention include 2-tridecyl
amine, 2-nonyldecylamine, 7-pentadecylamine, 10-nonyl
decylamine, l2-tricosylamine, IS-pentatriacontylamine, 2
tnidecenylamine, l2-tricosenylamine, 2-amino-2-methyl
nonane, 2-aminc-Z-propyloctadecane, 4-amino-4-nonyl
docosane, l-phenyl-l-octyla-mine, 2~amino—2-(p-amiuo
50 tached to a secondary carbon atom.
phenyl)decane, 4-arnino-1-(m-chlorophenyl)pentadeeene,
1-chloro-3-aminoheneicosane, 1-(2,4,6-trichlorophenyl)
2 - aminoundecane,
1 - amino-1-( B-naphthyDdecane,
Exam ple‘ II
The following table discloses the solubility of three
long chain aliphatic u-primary amines in water and
n-hexane (Skellysolve B), together with the solubility of
three long chain salts wherein the primary amine is at
l
aceto-3-aminohexadecane and 2- (p-nitrophenyl)-3-amino 55
B-methylnonane.
All of the 3,6-endoxohydrophthalic acids and their
anhydrides are useful in formulating the amine salts of
our invention. Thus, the di, tetra and hexahydrophthalic
acids or their monovalent radical substituted analogs are 60
useful in preparing oil-soluble amine salts. Radicals
which can be substituted for the hydrogens on the hydro
3,6-endoxohexahydro-
Solubility, g./100 mls. of solvent
phthalic salt, Amine
Temp, ______________________
° 0.
Water
n-hexane
Radical
n-hexyl _______________ __
26
Miscible in all
0.079.
n-dodecyl __________ __
n—octadecyl___
_____ __
26
27
0.045 __________ __
0.003 __________ __
0.150.
0.135.
8~pentadecyl ________ __
30
0.044 __________ __
Miscible in all
10-nonyldecyl.
__
30
0.021 (0.032) _ .___
Do.
l?rtricosyl ____________ __
30
0.036 __________ _-
Do.
proportions.
portions.
phthalic molecule include halogens, for instance chlorine
and bromine; alkyl radicals; acyl radicals, alkoxy radicals,
Example III
*aryloxy, acyloxyalkyl and nitric radicals. We prefer to 65
Using
a
fog
nozzle,
2 pounds of a 10% solution of the
use the unsubstituted hydrophthalic acids and particularly
salt obtained from 3,6-endoxohexahydrophthalic acid and
prefer to use the hexahydrophthalic acid and anhydride
pentadecylamine dissolved in petroleum ether are sprayed
in forming our desired amine salts.
on a ?eld of weeds common to northern Illinois. With
Good yieds of the oil-soluble amine salts are obtained
in a ‘few days pronounced burning is apparent and with
by contacting a desired amine with ‘an equivalent amount
‘of a desired 3,6-endoxohydrophthalic acid or anhydride
at temperatures of "about 50 to about 80° C. Both lower
the passage of a week or two almost total weed destruc
tion is noted.
3,097,088
3
4
Example IV
To defoliate privit, Ligustrum vulgare, a 3% solution
3. Oil soluble primary amine salts of a compound se
lected from the group consisting of 3,6~endoxohydro
ph-thalic acids and 3,6-endoxohydrophthalic anhydrides,
of the Z-tridecylamine salt of 3,6-endoxohexahydro
said primary amine having the primary amine radical at
phthalic acid in 5 SAE motor oil is sprayed on the. plant.‘
Within a few days abscission of the leaves begins and 5 tached to a carbon atom selected from the group con
sisting of secondary and tertiary carbon atoms and Where
continues until the plant is almost stripped. Some burn~
ing is noted.
in at least one'of ‘the organic radicals attached to the
amine substituted carbon atom contains from about 8 to
18 carbon atoms.
Example V
A solution suitable for killing most trees can be pre 10
pared by dissolving 25 parts by weight of the l2-tricosyl
4. Oil soluble primary salts of 3,6-endoxohexahydro
phthalic acid, said primary amine having the amine radi
amine salt of 3,6-endoxotetrahydrophthalic acid in 75
cal attached to a carbon atom selected from the group
parts corn oil.
consisting of secondary and tertiary carbon atoms and
Now having described our invention, what we claim is:
' wherein at least one of the organic radicals attached to
1. Plant growth regulatory compositions comprising 15 the amine substituted carbon atom contains from about
solutions having an effective concentration of primary
amine salts of 3,i6endoxolhexahydrophthalic acid in oil,
said primary amine salts having the primary amine rad
8 to 18 carbon atoms.
5. The Z-tridecylamine salt of 3,6-endoxoheXa-hydro
phthalic acid.
.
.
6. The 2-nonyldecylamine salt of 3,6-endoxohexahy
consisting of secondary and tertiary carbon atoms and 20 drophthalic acid.
ical attached to a carbon atom selected from the group
wherein at least one of the" organic radicals attached to
the amine substituted carbon atom contains from about
8 to about 18 carbon atoms.
'
. 7. The 8-pentadecylamine salt of 3,6»endoxohexahy
drophthalic acid.
8. The l0~nonyldecylamine salt of 3,6-endoXohexa-hy
2. In a method of regulating plant growth, the im-v . drophthalic acid.
provement comprising contacting a plant with a solution 25
9. The 12-tricosylaniine salt of 3,6-endoxohexahy
drophthalic acid.
of a primary amine salt of 3,6-endoxohexahydrophthalic
acid in oil, said primary amine having the amine radical
References Cited in the ?le of this patent
attached to a carbon atom selected from the group con
sisting of secondary and tertiary carbon atoms and said
UNITED STATES PATENTS
solution applied at a rate su?icient to promote plant
growth regulating effect and wherein the amine con
tains at least one organic radical having from about 8 to
about 18 carbon atoms vattached to the amine substi
tuted carbon atom.
2,550,494
2,576,081
2,609,286
‘2,637,642
2,900,411
Olin ________________ __ Apr. 24,
Tischler et al. ________ __ Nov. 20,
Tischler _____________ __ Sept. 2,
Tischler ______________ __ May 5,
Harwood et al. _______ __ Aug. 18,
1951
1951
1952
1953
1959
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