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Патент USA US3084104

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3,084,094
1C6
Patented Apr. 2, 1963
2
sentative compounds comprising this group of haloalkyl
3,0s4n94
Samuel I. Ger-tier, Washington, D.C.,
dedicated to the public
No Drawing. Filed ca. 4, 1955, Ser. No. 538,537
esters.
NEMATOCHDAL HALOALKYL ACID ESTER
TABLE I. NEMATOCIDAL ACTION OF HALOALKYL
ESTERS AGAINST Heterodera Rostochiensis
8 Claims. ((11.167-22)
(Granted under Title 35, US. Code (1952), sec. 266)
Concentra
Name of Toxic Compound
A non-exclusive, irrevocable, royalty-free license in the
invention described, for all governmental purposes, 10
throughout the world, with the power to grant sublicenses
for such purposes, is hereby granted to the Government
of the United States of America.
The patent rights for the United States in any inven
tion in the patent to be granted on this application are
dedicated to the public.
This invention relates to nematocides, their prepara
tion and their method of application. 1
tion, per
cent by
No. of
weeks be
fore ex- '
amining
cysts
Percent
Mortality
of Nema
todes
100
100
100
Butyl chloroaeetate _____________ __
Do _____________ ..
H.
100
100
2-Ch1oro1sopropy1 Z-chloropro
pionate _______________________ __
p-Methylcyclohexyl 2-chlor0pro
oco0:0
100
8800SOH
pionate _______________________ __
2-ChIl)or0ethyl 3-chloropropionate
Nematodes belong to a class of unsegmented worms
of the phylum Nemathelminthes. Certain species of this
class of worm, members of the subfamily Pratylenchinae
p
are known to effect a number ‘of subtropical ‘and tropical
u
c _____________________ __
2-Octyl 3-chl0roprop1onate ______ _ _
plants. They have been found in the roots of citrus
Z-Ethylhexyl 3-chloropropionate. _
2-Butyloety1 3-chloropropionate- _
and a wide rvariety of other plants including many orna
mentals. These root inhibiting nematodes are believed
Bengl 3-chloropropionate ...... _ o _________________ __
to be responsible for “spreading decline” in citrus and
cause millions of dollars of annual damage in the United
D0
4-Isopropylcyclohexyl
2-Phenoxyethyl B-chloropro
States.
It has ‘been found that esters of haloalkyl acids are
pionate _______________________ __
effective agents for treating the roots of plants for the 30
pionate _______________________ _
control of harmful nematodes contained therein.
These esters can be represented by the general formula
EXAMPLE II
R-(?J-O R1
0
35
Nematocide Tests Using Pratylenchus sp.
For these tests the nematocidal emulsions were pre
wherein R is selected from a group consisting of
pared as in Example I using concentrations of from
GHi-—-, CH;—(|JH—- and urn-Cirr
0.1 percent to 1.0 percent by 'volume. ‘Ornamental plants
such as azalea, philodendron, hibiscus, Chinese evergreen,
40 midget palm and the like, the roots of which were infested
and wherein R1 is selected from a group comprising an
with meadow nematode (Pratylenchus sp.) were used
alkyl group, a halogen-substituted alkyl group, a cyclo
as a host. The roots of these plants were washed free
aliphatic group, an alkyl-substituted cycloaliphatic group,
of adherent soil and the excess Water removed prior to
an aralkyl group and an aroxyalkyl group.
' '
The compounds were prepared by the esteri?cation 45 treatment. The plants were then arranged in the treat
ing vessels so that only the roots were immersed in the
of the halogenated acid with the required alcohol by
nematocidal medium for one hour. Splashing is avoided
methods known in the art, using a suitable catalyst, such
on the rest of the plant to prevent any possibility of
as sulphuric acid or toluene-sulfonic acid.
The following examples illustrate the effectiveness of
injury to foliage. The plants are then removed, replanted
times as much of a Wetting agent, such as Triton X-lOO 55
TERS AGAINST PRATYLENCHUS SP.
the compositions made according to this invention. 50 in sterile soil and examined at daily intervals. The roots
were chopped in a Waring Blendor, the nematodes col
Nematocide test compositions according to this invention
‘looted by sieving and the e?ectiveness of the control thus
contain from a minimum of 0.001 percent to 1.0 percent
determined.
of eliective compound on a volume-volume basis in an
TABLE II.——NEMATOCIDAL ACTION OF EALOALKYL ES
aqueous medium having dissolved therein from 2 to 10
or Tergitol 4, by volume as the toxicant. Speci?c test
organisms were the golden nematode (Heterodera
rostochiensis) and the meadow nematode (Pratylenchus
Name of Toxic Compound
EXAMPLE 1
tlon, per-
percent
cent by
control
volume
sp.).
Nematocide Tests Using Heterodera Rostochiensis
Nematocidal emulsion compositions were prepared by
Concentra- Minimum,
60
Butyl chloroacetate _________________________ __
0.01
98
2-Isopropylcyolohexyl chloroacetate _ _ _
1. 0
90-95
2-seo-Butylcyclohcxyl chloroaCetate. _ _
1. 0
90-95
Z-Chlorois opropyl 2-chlor0propionate. -
1. 0
90-95
p-Methylcyelohexyl 2-chloroproplonat
1. 0
90-95
Z-Chloroethyl ii-chloropropionate ____ _ _
0. 01
98
treating an aqueous mixture containing from 0.001 to
2-Methylpentyl 3-ch1oropropionote__
1. 0
90-95
1.0 percent by volume of the nematocide with 0.005
Z-Ootyl 3-chloropropionate _____ .1. 0
90-95
65
2-Ethylhexyl 3-chloropropionate._
1. 0
90-95
to 5.0 percent of Triton X-lOO. 1A cyst mixture con
2-Buty1octyl 3-chloropropionate..
1. 0
90-95
taining 100-300 nematode cysts per test was dipped into
Benzyl 3-chloropropionate ______ __
____
1. 0
90-95
Cyclohexyl 3~eh1oropropionate ______________ _ _
1. 0
90-95
the haloalkyl ester composition ‘for periods from 1 to
4-Isopropylcyclohexyl 3-chlor0pr0pionate ____ _ _
1. 0
90-95
30 minutes. After removing from the toxicant the cysts
Z-Phenoxyethyl 3~chloropropionate .......... _.
0. 1
98
were set aside and examined after a period of weeks and 70
the percentage of nonviable nematodes determined. The
These nematocidal compositions may be applied to
following table shows the results on a number of repre
growing plants in the ?eld ‘by treating the soil around
3,084,094.
3
4
todes which comprises applying to nematode-infested roots
of the plants a haloalkyl ester of the formula
the roots. For this purpose the composition is applied
in a suitable manner at the rate of 10 to 50 pounds of
active ingredient per acre. The compositions may also
be used in greenhouses.
I claim:
1. A method of preventing damage to plants by-nema
todespwhich comprises contacting the nematodes with a
where R is a radical selected from the group consisting of
ClCH2—,
GHQ-011
haloalkyl ester of the formula
10 and ClCHT-CH2-— and where R1 is a radical selected
from the group consisting of alkyl, halogen-substituted
where R is a radical selected from the group consisting
alkyl, cyclohexyl, alkyl-substituted cyclohexyl, benzyl, and
of ClCH2—,
phenoxyethyl, the ‘hydrocarbon moiety of the radical R1
containing from 2 to 12 carbon atoms.
CHiCH
<51
15
References Cited in the ?le of this patent
UNITED STATES PATENTS
and ClCH2—CH2—— and where R1 is a radical selected
from the group consisting of alkyl, halogenisubstituted
alkyl, cyclohexyl, alkyl-substituted cycloheXyl, benzyl,
and phenoxyethyl, the hydrocarbon moiety of the radical 20
R1 containing from 2 to 12 carbon atoms.
2. The method of claim 1 wherein the haloalkyl ester
is butyl chloroacetate.
3. The method of claim 1 wherein-the haloalkyl ester
is 2-chloroethyl 3-chloropropionate.
4. The method of claim 1 wherein the haloalkyl ester
is 2-phenoxyethyl 3-chlor0propionate.
5. The method of claim lewherein the haloalkyl ester
is 2-isopropylcyclohexyl chloroacetate.
6. The method of claim lvwherein the haloalkyl ester 30
is benzyl 3-chloropropionate.
7. A method of preventing damage to plants by nema
todes which comprises applying to nematode-infested soil
a haloalkyl ester of the-formula
35
where R is a radical selected from the group consisting of
C1CHr-3
1,851,040
1,982,909
~Fikentscher et al _______ __ Mar. 29, 1932
Flint _________________ __ Dec. 4, 1934
‘2,217,905
Hoffman ____' _________ __ Oct. 15, 1940
2,282,732
2,377,446
2,415,251
2,422,728
2,430,326
Lean ________________ __ May 12,
Payne ________________ _._ June 5,
Leavitt ________________ __ Feb. 4,
Gresham et a1 _________ __ June 24,
Cheney _______________ __ Nov. 4,
2,448,265
Kagy ________________ __ Aug. 31, 1948
2,502,244
2,543,580
2,726,485
2,730,547
2,770,638
2,779,680
2,794,727
Carter _______________ _- Mar. 28,
Kay _________________ __ Feb. .27,
Thomas ______________ __ Dec. 13,
Dye _________________ _._ Jan. 10,
Giolito ______________ __ Nov. 13,
Wolf _________________ __ Jan. 29,
Barrons _______________ __ June 4,
1950
1951
1955
1956
1956
1957
1957
2,802,021
2,802,818
2,802,831
2,809,983
Heininger _____________ __ Aug. 6,
Wheeler ______________ _.. Aug. 13,
Wheeler ______________ __ Aug. 13,
Heining‘er _____________ _- Oct. 15,
1957
1957
1957
1957
1942
1945
1947
1947
1947
and ClCH2—-‘CH2-- and where R1 is a radical selected
OTHER REFERENCES
Hiemenz et al.: J. Am. Chem. Soc. 71 (1949), pp.
1137-8.
Roark et al.: 1nd. Eng. Chem. 20 (1928), pp. 512-3.
from the group ‘consisting of alkyl, halogen-substituted
Webster’s ‘New International Dictionary of the English
omen
c1
alkyl, c'yclohexyl, ‘alkyl-substituted cyclohexyl, benzyl,
40
45 Language, 2nd Ed., 1940, G. & C. Merriman & Co., p.
and phenoxyethyl, the hydrocarbon moiety of the radical
818.
R1 containing from 2 to 12 carbon atoms.
8. A method of preventing damage to plants by nema
King: US. Dept. Agr. Handbook No. 69, May 1954, pp.
29, 292.
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