U.S. patent application number 16/131412 was filed with the patent office on 2019-03-21 for feeding deterrence in agricultural pests such as hemiptera, lepidoptera and coleoptera.
The applicant listed for this patent is BEDOUKIAN RESEARCH, INC.. Invention is credited to Robert H. BEDOUKIAN.
Application Number | 20190082690 16/131412 |
Document ID | / |
Family ID | 49514699 |
Filed Date | 2019-03-21 |
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United States Patent
Application |
20190082690 |
Kind Code |
A1 |
BEDOUKIAN; Robert H. |
March 21, 2019 |
FEEDING DETERRENCE IN AGRICULTURAL PESTS SUCH AS HEMIPTERA,
LEPIDOPTERA AND COLEOPTERA
Abstract
Compounds are used as agents that deter feeding on crops by
agricultural pests, such as hemiptera, lepidoptera and coleoptera,
including, but not limited to, stink bugs, codling moth larvae and
granary weevils. Feeding deterrence is obtained by contact of the
insects with at least one of the compounds of the structure (I)
wherein ##STR00001## R is --OH, .dbd.O, --OC(O)R.sub.4, --OR.sub.6
or --(OR.sub.6).sub.2, wherein each R.sub.6 is independently an
alkyl group containing from 1 to 4 carbon atoms and R.sub.4 is a
branched or straight chain, saturated or unsaturated, hydrocarbyl
group with zero to two double bonds and from 1 to 15 carbon atoms;
X is O or CH.sub.2 with the proviso that when X is O, R can only be
.dbd.O; each Z is independently (CH) or (CH.sub.2); y is a numeral
selected from 1 and 2; R.sub.1 is H or a branched or straight
chain, saturated or unsaturated hydrocarbyl group with zero to two
double bonds and from 1 to 15 carbon atoms; R.sub.2 is H or a
branched or straight chain, saturated or unsaturated hydrocarbyl
group with zero to three double bonds and from 1 to 15 carbon
atoms; R.sub.3 is selected from H, a branched or straight chain,
saturated or unsaturated hydrocarbyl group with zero to three
double bonds and from 1 to 15 carbon atoms, --(CH.sub.2).sub.nOH,
--C(O)OR.sub.5, --CH.sub.2C(O)OR.sub.7, --CH.sub.2C(O)R.sub.8,
--C(O)NR.sub.9R.sub.10, and --CH.sub.2C(O)NR.sub.11R.sub.12 where
each of R.sub.5, R.sub.7, R.sub.8, R.sub.9, R.sub.10, R.sub.11 and
R.sub.12 is independently selected from H and a branched or
straight chain, saturated or unsaturated hydrocarbyl group with
zero to three double bonds and from 1 to 15 carbon atoms and n is
an integer of from 1 to 12; the bond between the 2 and 3 positions
in the ring structure may be a single or a double bond; and wherein
the compounds of structure (I) contain from 9 to 20 total carbon
atoms in the compounds.
Inventors: |
BEDOUKIAN; Robert H.; (West
Redding, CT) |
|
Applicant: |
Name |
City |
State |
Country |
Type |
BEDOUKIAN RESEARCH, INC. |
Danbury |
CT |
US |
|
|
Family ID: |
49514699 |
Appl. No.: |
16/131412 |
Filed: |
September 14, 2018 |
Related U.S. Patent Documents
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Application
Number |
Filing Date |
Patent Number |
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14390826 |
Oct 6, 2014 |
10111429 |
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PCT/US2013/000120 |
Apr 30, 2013 |
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16131412 |
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61687920 |
May 2, 2012 |
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Current U.S.
Class: |
1/1 |
Current CPC
Class: |
A01N 37/02 20130101;
A01N 31/06 20130101; A01N 37/42 20130101; A01N 35/06 20130101; A01N
43/16 20130101; A01N 43/08 20130101; A01N 37/18 20130101; A01N
49/00 20130101; A01N 37/06 20130101; A01N 37/36 20130101 |
International
Class: |
A01N 43/16 20060101
A01N043/16; A01N 37/02 20060101 A01N037/02; A01N 37/36 20060101
A01N037/36; A01N 37/42 20060101 A01N037/42; A01N 43/08 20060101
A01N043/08; A01N 31/06 20060101 A01N031/06; A01N 37/18 20060101
A01N037/18; A01N 35/06 20060101 A01N035/06; A01N 49/00 20060101
A01N049/00; A01N 37/06 20060101 A01N037/06 |
Claims
1. A method for deterring the feeding of one or more agricultural
pests selected from the group consisting of hemiptera, lepidoptera
and coleoptera on food or crops is obtained by: contacting of the
pests with an effective amount of a formulation comprising at least
one of the compounds of the structure (I) ##STR00013## wherein R is
selected from the group consisting of --OH, .dbd.O, --OC(O)R.sub.4,
--OR.sub.6, and --(OR.sub.6).sub.2, wherein each R.sub.6 is
independently selected from an alkyl group containing from 1 to 4
carbon atoms and R.sub.4 is a branched or straight chain, saturated
or unsaturated hydrocarbyl group with zero to two double bonds and
from 1 to 15 carbon atoms; X is O or CH.sub.2 with the proviso that
when X is O, R can only be .dbd.O; each Z is independently selected
from the group consisting of (CH) and (CH.sub.2) y is a numeral
selected from 1 and 2; R.sub.1 is selected from the group
consisting of H and a branched or straight chain, saturated or
unsaturated hydrocarbyl group with zero to two double bonds and
from 1 to 15 carbon atoms; R.sub.2 is selected from the group
consisting of H and a branched or straight chain, saturated or
unsaturated hydrocarbyl group with zero to three double bonds and
from 1 to 15 carbon atoms; R.sub.3 is selected from H, a branched
or straight chain, saturated or unsaturated hydrocarbyl group with
zero to three double bonds and from 1 to 15 carbon atoms,
--(CH.sub.2).sub.nOH, --C(O)OR.sub.5, --CH.sub.2C(O)OR.sub.7,
--CH.sub.2C(O)R.sub.8, --C(O)NR.sub.9R.sub.10, and
--CH.sub.2C(O)NR.sub.11R.sub.12 where each of R.sub.5, R.sub.7,
R.sub.8, R.sub.9, R.sub.10, R.sub.11 and R.sub.12 is independently
selected from H and a branched or straight chain, saturated or
unsaturated hydrocarbyl group with zero to three double bonds and
from 1 to 15 carbon atoms, and n is n integer of from 1 to 12; the
bond between the 2 and 3 positions in the ring structure may be a
single or a double bond, and wherein the compounds of structure (I)
contain from 9 to 20 total carbon atoms in the compounds.
2. The method according to claim 1 wherein the agricultural pest is
selected from the group consisting of: cicadas, aphids, stink bugs,
butterflies, moths and beetles.
3. The method according to claim 1 wherein the compounds of
structure (I) have from 10 to 16 carbon atoms in the compound.
4. The method according to claim 1 wherein the at least one
compound of structure (I) is a compound wherein: R is selected from
the group consisting of --OH and .dbd.O, X is CH.sub.2, y is 1 or
2, each Z is selected from the group consisting of (CH) and
(CH.sub.2), the bond between positions 2 and 3 in the ring is a
single bond, one of R.sub.1 and R.sub.2 is H or --CH.sub.3 and the
other of R.sub.1 and R.sub.2 is a hydrocarbyl group containing from
9 to 15 carbon atoms and 0 to 3 double bonds, and R.sub.3 is H.
5. The method of claim 1 wherein the at least one compound of
structure (I) is a compound wherein: R is selected from the group
consisting of --OH and .dbd.O, X is CH.sub.2, y is 1 or 2, each Z
is selected from (CH) and (CH.sub.2), the bond between positions 2
and 3 in the ring is a single or double bond, one of R.sub.1 and
R.sub.2 is H and the other of R.sub.1 and R.sub.2 is a hydrocarbyl
group containing from 9 to 15 carbon atoms and 0 to 3 double bonds,
and R.sub.3 is selected from the group consisting of --C(O)OR.sub.5
and --CH.sub.2C(O)R.sub.8 where R.sub.5 and R.sub.8 are each
selected from a hydrocarbyl group containing from 1 to 6 carbon
atoms.
6. The method according to claim 5 wherein R is .dbd.O, y is 1, the
bond between positions 2 and 3 in the ring is a single bond, and
R.sub.2 and R.sub.5 are each --CH.sub.3.
7. The method according to claim 1 wherein the at least one
compound of structure (I) is a compounds wherein: R is .dbd.O, X is
O, y is 1 or 2, each Z is selected from the group consisting of
(CH) and (CH.sub.2), the bond between positions 2 and 3 of the
rings is a single or double bond, one of R.sub.1 and R.sub.2 is H
and the other of R.sub.1 and R.sub.2 is a hydrocarbyl group
containing group containing from 9 to 15 carbon atoms and 0 to 3
double bonds, and R.sub.3 is selected from the group consisting of
--C(O)OR.sub.5 and --CH.sub.2C(O)R.sub.8 where R.sub.5 and R.sub.8
are each selected from a hydrocarbyl group containing from 1 to 6
carbon atoms and wherein the total number of carbon atoms in the
compounds of structure (I) is from 11 to 17.
8. The method according to claim 7 wherein the bond between
positions 2 and 3 of the rings is a single bond and R.sub.5 and
R.sub.7 are each selected from a hydrocarbyl group containing from
3 to 5 carbon atoms.
9. The method according to claim 7 wherein the bond between
positions 2 and 3 of the rings is a single bond and R.sub.5 and
R.sub.7 are each --CH.sub.3.
10. The method according to claim 1 wherein the at least one
compound of structure (I) is a compound wherein: R is .dbd.O, X is
O, y is 1 or 2, each Z is selected from (CH) and (CH.sub.2), the
bond between positions 2 and 3 in the ring is a single bond,
R.sub.1 is an alkyl group containing from 5 to 13 carbon atoms,
R.sub.2 is selected from the group consisting of H or --CH.sub.3,
and R.sub.3 is H.
11. The method according to claim 10 wherein: R.sub.1 is an alkyl
group of from 5 to 10 carbon atoms such that the compound of
structure (I) contains from 11 to 14 total carbon atoms.
12. The method according to claim I wherein the at least one
compound of structure (I) is selected from the group consisting of:
##STR00014## ##STR00015## ##STR00016##
13. The method according to claim 1 wherein the at least one
compound of structure (I) is selected from the group consisting of:
##STR00017## ##STR00018##
14. The method according to claim 1 wherein the at least one
compound of structure (I) is selected from the group consisting of
##STR00019## ##STR00020##
15. The method according to claim 1 wherein the at east one
compound of structure (I) is selected from the group consisting of:
##STR00021## ##STR00022## ##STR00023##
16. The method according to claim 1 wherein the at least one
compound of structure (I) is selected from the group consisting of
##STR00024##
17. The method according to claim I wherein the at least one
compound of structure (I) is applied to crops, agricultural or
ornamental trees, plants, vegetation, produce or packaging
materials for plants or crops by way of a formulation selected from
the group consisting of direct spray formulations, fogger
formulations, microencapsulated formulations, soil treatment
formulations, seed treatment formulations, injectable formulations
for injection into or onto plants or crops, and formulations for
evaporative devices.
18. The method of claim 1 wherein the at least one compound of
structure (I) is selected from the group consisting of : methyl
apritone, methyl dihydrojasmonate, propyl dihydrojasmonate, methyl
dihydrojasmolate, gamma-dodecalactone, gamma-tridecalactone, gamma
methyl dodecalactone, gamma methyl tridecalactone.
3-methyl-5-propyl-2-cyclohexenone,
3-methyl-5-isobutyl-2-cyclohexenone,
3-methyl-5-isobutyl-2-cyclohexenol,
3-methyl-5-pentyl-2-cyclohexenone,
3-methyl-5-hexyl-2-cyclohexenone, and
3-methyl-5-heptyl-2-cyclohexenone.
19. The method according to claim 1 wherein the at least one
compound of the structure (I) is present in the formulation in an
amount sufficient to provide increased pest repellency or mortality
over control pest repellency or mortality of at least 1%.
20. The method of claim 1 wherein the formulation is used to treat
food or crops such that the treated food or crops have from about
0.05 to about 250 mg/sq. in. of at least one of the compounds
thereon.
Description
CROSS-REFERENCED APPLICATIONS
[0001] This application is a continuation of U.S. patent
application Ser. No. 14/390,826, filed Oct. 6, 2014, which claims
priority to international application PCT/US13/00120, filed Apr.
30, 2013, and U.S. Application Ser. No. 61/687,920, filed May 2,
2012, all of which are incorporated herein by reference.
BACKGROUND
1. Field of the Disclosure
[0002] This disclosure relates to the use of compounds as agents
that deter feeding on crops by agricultural pests such as
hemiptera, lepidoptera and coleoptera including, but not limited
to, stink bugs, codling moth larvae and granary weevils.
[0003] The active feeding deterrence agents of this disclosure are
an effective control agent against agricultural pests such as
hemiptera, lepidoptera and coleoptera. Hemiptera includes cicadas,
aphids and stink bugs such as the Brown Marmorated Stink Bug.
Lepidoptera includes butterflies and moths such as the Codling
Moth. Coleoptera are beetles and the order contains granary
weevils.
2. Discussion of the Background Art
[0004] Agricultural pests including but not limited to the brown
marmorated stink bug, codling moth and granary weevil are known to
feed on various crops causing damage to fruits, vegetables and
other plant life. The cost of this damage is extensive and leads to
hardship among growers.
[0005] In the Mid-Atlantic region, where brown marmorated stink
bugs are well established, they caused an estimated $37 million in
damage in apple crops alone in 2010, the most recent year for which
data are available. [Darryl Fears, "Stink bugs migrating to deep
south", Washington Post, Mar. 16, 2012]. Aside from apples, the bug
will feed on nearly anything, including cherries, tomatoes, grapes,
lima beans, soybeans, green peppers and peaches.
[0006] Codling moth larvae penetrate into apples and pears and
tunnel to the core, leaving holes in the fruit that are filled with
reddish-brown, crumbly droppings. If left uncontrolled, larvae can
cause substantial damage, often infesting 20 to 90% of the fruit,
depending on the variety and location. Late maturing varieties are
more likely to suffer severe damage than early varieties. [J. L.
Caprile and P. M. Vossen, Pest Notes: Codling Moth UC ANR
Publication 7412, May 2011].
[0007] In walnuts, codling moth larvae feed on the kernels. Nuts
damaged early in the season when the nuts are quite small will drop
off trees soon after damage occurs. Nuts damaged later in the
season will remain on trees, but their kernels are inedible.
Walnuts aren't as favored a host as apples and pears, and untreated
trees might incur very little to modest damage (10 to 15% of the
nuts), depending on the variety and location. [Pest Notes, May
2011]
[0008] Phosmet, a phthalimide-derived, non-systemic,
organophosphate insecticide is the primary means of controlling
codling moth damage to apples. This material is on the US Emergency
Planning list of extremely hazardous substances and is highly toxic
to bees. The materials covered in this patent application would be
a much gentler means of deterring the larvae and controlling moth
infestation.
[0009] Granary weevils are attracted to and will attack all kinds
of grains and grain products. These products will include such
materials as wheat, corn, barley, or rice. In stored food products,
they may be found in materials like macaroni or spaghetti. Adult
weevils will feed on the same foods as the larvae. However, because
they do not need to develop in the inside of whole grains like
larvae do, they are not limited to just one grain or in other
words, they are not restricted in their diets.
[http://www.pestmall.com/blog/pest-info/other-pests/granary-weevil-biolog-
y]
[0010] Control of weevils is quite difficult as they live and breed
in our food sources. Use of pyrethrins is an option, but food
shouldn't be sprayed directly. Use of our materials may be sprayed
directly on crops, seeds, agricultural or ornamental trees, plants,
vegetation, produce or packaging materials so they provide a better
alternative to traditional insecticides.
SUMMARY
[0011] In accordance with this disclosure, feeding deterrence of
crops by agricultural pests such as hemiptera, lepidoptera and
coleoptera is obtained by contact of the insects with at least one
of the compounds of the structure (I)
##STR00002##
wherein: [0012] R is selected from --OH, .dbd.O, --OC(O)R.sub.4,
--OR.sub.6, and --(OR.sub.6).sub.2, wherein each R.sub.6 is
independently selected from an alkyl group containing from 1 to 4
carbon atoms and R.sub.4 is a branched or straight chain, saturated
or unsaturated, hydrocarbyl group with zero to two double bonds and
from 1 to 15 carbon atoms; [0013] X is O or CH.sub.2 with the
proviso that when X is O, R can only be .dbd.O; [0014] each Z is
independently selected from (CH) and (CH.sub.2); [0015] y is a
numeral selected from 1 and 2; [0016] R.sub.1 is selected from H or
a branched or straight chain, saturated or unsaturated hydrocarbyl
group with zero to two double bonds and from 1 to 1.5 carbon atoms;
[0017] R.sub.2 is selected from H and a branched or straight chain,
saturated or unsaturated hydrocarbyl group with zero to three
double bonds and from 1 to 15 carbon atoms; [0018] R.sub.3 is
selected from H, a branched or straight chain, saturated or
unsaturated hydrocarbyl group with zero to three double bonds and
from 1 to 15 carbon atoms, --(CH.sub.2).sub.nOH, --C(O)OR.sub.5,
--CH.sub.2C(O)OR.sub.7, --CH.sub.2C(O)R.sub.8,
--C(O)NR.sub.9R.sub.10, and --CH.sub.2C(O)NR.sub.11R.sub.12 where
each of R.sub.5, R.sub.7, R.sub.8, R.sub.9, R.sub.10, R.sub.11 and
R.sub.12 is independently selected from H and a branched or
straight chain, saturated or unsaturated hydrocarbyl group with
zero to three double bonds and from 1 to 15 carbon atoms and n is
an integer of from 1 to 12; [0019] the bond between the 2 and 3
positions in the ring structure may be a single or a double bond;
and [0020] wherein the compounds of structure (I) contain from 9 to
20 total carbon atoms in the compounds. The disclosure also
includes optical isomers, diastereomers and enantiomers of the
compounds of structure (I). Thus, at all stereocenters where
stereochemistry is not explicitly defined, all possible epimers are
envisioned.
[0021] The feeding deterrence compounds of this disclosure, which
could be applied directly to crops, seeds, agricultural or
ornamental trees, plants, vegetation, produce or packaging
materials for crops, have low mammalian toxicity and are similar to
naturally occurring materials used in flavor/fragrance
applications. Therefore, these provide a better method of control
for farmers and home owners. Additionally, the feeding deterrence
compounds of this disclosure have the potential to be used on
organic crops.
[0022] The compounds of structure (I) may be employed to defer
feeding by agricultural pests, such as hemiptera, lepidoptera and
coleoptera which include, but are not limited to, stink bugs,
codling moth larvae and granary weevils. The active compounds of
structure (I) may be employed in any suitable formulation, such as,
but not limited to, direct spray formulations, fogger formulations,
microencapsulated formulations, soil treatment formulations, seed
treatment formulations, injectable formulations for injection into
the plant and formulations for use in evaporative devices.
DETAILED DESCRIPTION OF EMBODIMENTS
[0023] Deterrence of feeding by agricultural pests, such as
hemiptera, lepidoptera and coleoptera including, but not limited
to, stink bugs, codling moth larvae and granary weevils is obtained
by contact of the insects with at least one of the compounds of the
structure (I)
##STR00003##
wherein [0024] R is selected from --OH, .dbd.O, --OC(O)R.sub.4,
--OR.sub.6, and --(OR.sub.6).sub.2, wherein each R.sub.6 is
independently selected from an alkyl group containing from 1 to 4
carbon atoms and R.sub.4 is a branched or straight chain, saturated
or unsaturated hydrocarbyl group with zero to two double bonds and
from 1 to 15 carbon atoms. [0025] X is O or CH.sub.2 with the
proviso that when X is O, R can only be .dbd.O; [0026] each Z is
independently selected from (CH) and (CH.sub.2); [0027] y is a
numeral selected from 1 and 2; [0028] R.sub.1 is selected from H or
a branched or straight chain, saturated or unsaturated hydrocarbyl
group with zero to two double bonds and from 1 to 15 carbon atoms;
[0029] R.sub.2 is selected from H and a branched or straight chain,
saturated or unsaturated hydrocarbyl group with zero to three
double bonds and from 1 to 15 carbon atoms; [0030] R.sub.3 is
selected from H, a branched or straight chain, saturated or
unsaturated hydrocarbyl group with zero to three double bonds and
from 1 to 15 carbon atoms --(CH.sub.2).sub.nOH, --C(O)OR.sub.5,
--CH.sub.2C(O)OR.sub.7, --CH.sub.2C(O)R.sub.8,
--C(O)NR.sub.9R.sub.10, and --CH.sub.2C(O)NR.sub.11R.sub.12 where
each of R.sub.5, R.sub.7, R.sub.8, R.sub.9, R.sub.10, R.sub.11 and
R.sub.12 is independently selected from H and a branched or
straight chain, saturated or unsaturated hydrocarbyl group with
zero to three double bonds and from Ito 15 carbon atoms, and n is n
integer of from 1 to 12; [0031] the bond between the 2 and 3
positions in the ring structure may be a single or a double bond;
and [0032] wherein the compounds of structure (I ) contain from 11
to 20 total carbon atoms in the compounds. The disclosure also
includes optical isomers, diastereomers and enantiomers of the
named structures. Thus, at all stereocenters where stereochemistry
is not explicitly defined, all possible epimers are envisioned.
[0033] A preferred group of feeding deterrence compounds are those
compounds of structure (I) wherein; [0034] R is selected from --OH
and .dbd.O, X is CH.sub.2, y is 1 or 2, each Z is selected from
(CH) and (CH.sub.2), the bond between positions 2 and 3 in the ring
is a single bond, one of R.sub.1 and R.sub.2 is H or --CH.sub.3 and
the other of R.sub.1 and R.sub.2 is a branched or straight chain,
saturated or unsaturated hydrocarbyl group containing from 9 to 15
carbon atoms and 0 to 3 double bonds, and R.sub.3 is H.
[0035] Another preferred group of feeding deterrence compounds are
those compounds of structure (I) wherein; [0036] R is selected from
--OH and .dbd.O, more preferably .dbd.O, X is CH.sub.2, y is 1 or
2, more preferably 1, each Z is selected from (CH) and (CH.sub.2),
the bond between positions 2 and 3 in the ring is a single or
double bond, more preferably a single bond, one of R.sub.1 and
R.sub.2 is H and the other of R.sub.1 and R.sub.2 is a branched or
straight chain, saturated or unsaturated hydrocarbyl group
containing from 9 to 15 carbon atoms and 0 to 3 double bonds, and
R.sub.3 is selected from --C(O)OR.sub.5 and --CH.sub.2C(O)R.sub.8
where R.sub.5 and R.sub.8 are each selected from a straight chain
or branched, saturated or unsaturated hydrocarbyl group containing
from 1 to 6 carbon atoms, and more preferably 3 to 5 carbon atoms
and still more preferably --CH.sub.3.
[0037] Another preferred group of feeding deterrence compounds are
those compounds of structure (I) wherein [0038] R is .dbd.O, X is
O, y is 1 or 2, each Z is selected from (CH) and (CH.sub.2), the
bond between positions 2 and 3 of the rings is a single or double
bond, more preferably a single bond, one of R.sub.1 and R.sub.2 is
H and the other of R.sub.1 and R.sub.2 is a branched or straight
chain, saturated or unsaturated hydrocarbyl group containing from 9
to 15 carbon atoms and 0 to 3 double bonds, and R.sub.3 is selected
from --C(O)OR.sub.5 and --CH.sub.2C(O)R.sub.8 where R.sub.5 and
R.sub.7 are each selected from a hydrocarbyl group containing from
1 to 6 carbon atoms, and more preferably 3 to 5 carbon atoms and
still more preferably --CH.sub.3 and wherein the total number of
carbon atoms in the compounds of structure (I) is from 9 to 20,
more preferably from 9 to 14 total carbon atoms.
[0039] Another preferred group of feeding deterrence compounds are
those compounds of structure (I) wherein R is .dbd.O, X is O, y is
1 or 2, each Z is selected from (CH) and (CH.sub.2), the bond
between positions 2 and 3 in the ring is a single bond, R.sub.1 is
a branched or straight chain, saturated or unsaturated alkyl group
containing from 5 to 13 carbon atoms, R.sub.2 is H or --CH.sub.3,
R.sub.3 is H, and more preferably where R.sub.1 is an alkyl group
of from 5 to 10 carbon atoms such that the compound of structure
(I) contains from 11 to 14 total carbon atoms.
[0040] The active compounds of structure (I) may be employed in any
suitable formulation, such as, but not limited to, direct spray
formulations, fogger formulations, microencapsulated formulations,
soil treatment formulations, seed treatment formulations,
injectable formulation for injection into the plant and
formulations for use in evaporative devices. The formulations of
the active compounds will be such that the food or crops being
treated will have from about 0.05 to about 250 mg/sq. in.,
preferably about 0.25 to about 50 mg/sq. in., of the active
compounds thereon.
[0041] Representative examples of compounds of structure (I)
include, but are not limited to,
##STR00004## ##STR00005## ##STR00006## ##STR00007## ##STR00008##
##STR00009## ##STR00010## ##STR00011## ##STR00012##
[0042] Preferred compounds of structure (I) include methyl
apritone, methyl dihydrojasmonate, propyl dihydrojasmonate,
gamma-dodecalactone, gamma-tridecalactone, gamma methyl
dodecalactone, gamma methyl tridecalactone,
3-methyl-5-propyl-2-cyclohexenone,
3-methyl-5-isobutyl-2-cyclohexenone,
3-methyl-5-isobutyl-2-cyclohexenol,
3-methyl-5-pentyl-2-cyclohexenone,
3-methyl-5-hexyl-2-cyclohexenone, and
3-methyl-5-heptyl-2-cyclohexenone.
[0043] A test was designed to measure the repellency as feeding
deterrence in brown marmorated stink bugs (BMSB). Five replicates
of 5 BMSBs were introduced into test arenas, containing one 60
mm.times.15 mm Petri dish with treated filter papers in which a
food source (green bean) was attached, at the start of the
test.
[0044] The small Petri dishes containing the treated filter paper
and food source were covered with a fitted Petri dish lid in
between observation times, and were removed 5 minutes before each
observation time to prevent stink bugs from feeding until sated.
The distribution of the BMSBs was observed and documented hourly
for 5 hours.
TABLE-US-00001 TABLE 1 Compound in a 57% Ethanol:43% Repellency
averaged water solution over 5 hours Control (57% Ethanol:43% water
solution) 38% Methyl Dihydrojasmonate (3.5%) 90% Methyl
Dihydrojasmonate - Low epi (2.5%) 58% Methyl Dihydrojasmonate -
High epi (2.5%) 39% Propyl Dihydrojasmonate (3.5%) 100% Propyl
Dihydrojasmonate - Low epi (2.5%) 74% Propyl Dihydrojasmonate -
High epi (2.5%) 49% Para-Menthanediol (3.5%) 91%
Gamma-Dodecalactone (3.5%) 82% Gamma-Methyl Tridecalactone (3.5%)
67%
[0045] Another test was designed to measure the repellency as
feeding deterrence in Codling Moth larvae. The treatment was
applied to the surface of a proprietary laboratory media in a tray
with wells for each compound. The media was allowed to dry for
30-60 minutes so that larvae were not exposed to it as a liquid.
One first instar codling moth larva was then placed on the treated
media. The cover film was placed on the tray to prevent escapes.
Ten additional replicates treated with a 57% ethanol solution were
prepared to serve as controls. The larvae were observed at 24 hours
to determine if they burrowed into the media. After the 24 hour
reading, the larvae were extracted from the media to record any
mortality.
TABLE-US-00002 TABLE 2 Compound at 3.5% in a 57% Ethanol:43%
Repellency at water solution 24 hours Control (57% Ethanol:43%
water solution) 8% Para-Menthanediol 10% Propyl Dihydrojasmonate
59% Prenyl Dihydrojasmonate 79% Gamma-Dodecalactone 46% Methyl
Apritone 100% 3-Methyl-5-Propyl-2-Cyclohexenone 21%
3-Methyl-5-Propyl-2-Cyclohexenol 30%
3-Methyl-5-Heptyl-2-Cyclohexenone 95%
[0046] Mortality observations were also made for the above
protocol. The control was the 57% ethanol:43% water solution.
TABLE-US-00003 TABLE 3 Increased Mortality over Compound at 3.5% in
a 57% Ethanol:43% Control Mortality water solution at 24 hours
Para-Menthanediol 3% Propyl Dihydrojasmonate 18% Prenyl
Dihydrojasmonate 34% Gamma-Dodecalactone 37% Methyl Apritone 95%
3-Methyl-5-Propyl-2-Cyclohexenone 1%
3-Methyl-5-Propyl-2-Cyclohexenol 9%
3-Methyl-5-Heptyl-2-Cyclohexenone 93%
[0047] Ten replicates of 30 kernels of wheat were immersed into the
test compound and allowed to dry for 24 hours. The grains were then
transferred to a test container, and 10 granary weevils were
released. Test containers were secured and left for a 3 week
period. At the end of this time, the wheat grains were examined for
developing larvae and damage by larvae. The number of grains that
contained developing larvae or that showed damage was recorded. Ten
additional replicates treated with isopropyl alcohol were prepared
to serve as controls.
TABLE-US-00004 TABLE 4 Increased Increased Repellency Mortality
over Test compound, diluted in isopropyl vs. Control Control
alcohol Repellency Mortality Methyl Apritone (5%) 11% N/A Propyl
Dihydrojasmonate (5%) 8% N/A Gamma Tridecalactone (5%) 40% N/A
3-Methyl-5-Propyl-2-Cyclohexenone (5%) 66% 57%
3-Methyl-5-Isobutyl-2-Cyclohexenol (5%) 86% 93%
[0048] The feeding deterrent compounds of this disclosure may be
blended with active repellents or toxicants including, but not
limited to, NN-Diethyl-m-toluamide (DEET.RTM.) and
p-Menthane-3,8-diol (PMD).
[0049] While the disclosure has been described herein with
reference to the specific embodiments thereof, it will be
appreciated that changes, modification and variations can be made
without departing from the spirit and scope of the inventive
concept disclosed herein. Accordingly, it is intended to embrace
all such changes, modification and variations that fall with the
spirit and scope of the appended claims.
* * * * *
References