U.S. patent application number 13/663531 was filed with the patent office on 2013-03-14 for pesticidal compositions.
This patent application is currently assigned to DOW AGROSCIENCES LLC. The applicant listed for this patent is Dow AgroSciences LLC. Invention is credited to Zoltan L. Benko, Michael R. Loso, Timothy P. Martin, Benjamin M. Nugent, James M. Renga.
Application Number | 20130065912 13/663531 |
Document ID | / |
Family ID | 41726352 |
Filed Date | 2013-03-14 |
United States Patent
Application |
20130065912 |
Kind Code |
A1 |
Nugent; Benjamin M. ; et
al. |
March 14, 2013 |
PESTICIDAL COMPOSITIONS
Abstract
Pesticide compositions and their use in controlling pests are
provided.
Inventors: |
Nugent; Benjamin M.;
(Brownsburg, IN) ; Benko; Zoltan L.;
(Indianapolis, IN) ; Renga; James M.;
(Indianapolis, IN) ; Loso; Michael R.; (Carmel,
IN) ; Martin; Timothy P.; (Noblesville, IN) |
|
Applicant: |
Name |
City |
State |
Country |
Type |
Dow AgroSciences LLC; |
Indianapolis |
IN |
US |
|
|
Assignee: |
DOW AGROSCIENCES LLC
Indianapolis
IN
|
Family ID: |
41726352 |
Appl. No.: |
13/663531 |
Filed: |
October 30, 2012 |
Related U.S. Patent Documents
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Application
Number |
Filing Date |
Patent Number |
|
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12547049 |
Aug 25, 2009 |
8324209 |
|
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13663531 |
|
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61092077 |
Aug 27, 2008 |
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Current U.S.
Class: |
514/256 ;
514/247; 544/224; 544/242; 544/334 |
Current CPC
Class: |
C07D 239/26 20130101;
A01N 47/40 20130101; C07D 239/30 20130101; C07D 237/12 20130101;
A01N 47/34 20130101; A01N 47/24 20130101; A01N 43/78 20130101; A01N
51/00 20130101 |
Class at
Publication: |
514/256 ;
544/334; 544/224; 514/247; 544/242 |
International
Class: |
A01N 43/54 20060101
A01N043/54; C07D 237/12 20060101 C07D237/12; A01P 7/00 20060101
A01P007/00; C07D 239/26 20060101 C07D239/26; A01P 5/00 20060101
A01P005/00; C07D 239/30 20060101 C07D239/30; A01N 43/58 20060101
A01N043/58 |
Claims
1. A process to control pests of Phylum Nematoda, or Phylum
Arthropoda, or both, said process comprising applying a composition
comprising a compound having the following general formula:
##STR00020## wherein R1 is (a) an unsubstituted pyrimidinyl,
pyridazinyl, or pyrazinyl, or (b) a substituted pyrimidinyl,
pyridazinyl or pyrazinyl, wherein each substituted pyrimidinyl,
pyridazinyl, or pyrazinyl, has one or more substituents
independently selected from (C.sub.2-C.sub.6)alkenyl,
(C.sub.2-C.sub.6)alkenyloxy, (C.sub.1-C.sub.6)alkoxy,
(C.sub.1-C.sub.6)alkyl, (C.sub.2-C.sub.6)alkynyl,
(C.sub.2-C.sub.6)alkynyloxy, aryl, (C.sub.3-C.sub.6)cycloalkenyl,
(C.sub.3-C.sub.6)cycloalkenyloxy, (C.sub.3-C.sub.6)cycloalkyl,
(C.sub.3-C.sub.6)cycloalkoxy, halo, halo(C.sub.1-C.sub.6)alkyl, or
heterocyclyl; R2 is H, (C.sub.2-C.sub.6)alkenyl,
(C.sub.2-C.sub.6)alkenyloxy, (C.sub.1-C.sub.6)alkoxy,
(C.sub.1-C.sub.6)alkyl, (C.sub.2-C.sub.6)alkynyl,
(C.sub.2-C.sub.6)alkynyloxy, aryl, (C.sub.3-C.sub.6)cycloalkenyl,
(C.sub.3-C.sub.6)cycloalkenyloxy, (C.sub.3-C.sub.6)cycloalkyl,
(C.sub.3-C.sub.6)cycloalkoxy, halo, halo(C.sub.1-C.sub.6)alkyl, or
heterocyclyl; R3 is H, (C.sub.2-C.sub.6)alkenyl,
(C.sub.2-C.sub.6)alkenyloxy, (C.sub.1-C.sub.6)alkoxy,
(C.sub.1-C.sub.6)alkyl, (C.sub.2-C.sub.6)alkynyl,
(C.sub.2-C.sub.6)alkynyloxy, aryl, (C.sub.3-C.sub.6)cycloalkenyl,
(C.sub.3-C.sub.6)cycloalkenyloxy, (C.sub.3-C.sub.6)cycloalkyl,
(C.sub.3-C.sub.6)cycloalkoxy, halo, halo(C.sub.1-C.sub.6)alkyl, or
heterocyclyl; Optionally, R2 and R3 may form a ring wherein the
ring contains 3 or more ring atoms optionally containing an O, S,
or N atom; R4 is H, (C.sub.2-C.sub.6)alkenyl,
(C.sub.2-C.sub.6)alkenyloxy, (C.sub.1-C.sub.6)alkoxy,
(C.sub.1-C.sub.6)alkyl, (C.sub.2-C.sub.6)alkynyl,
(C.sub.2-C.sub.6)alkynyloxy, aryl, (C.sub.3-C.sub.6)cycloalkenyl,
(C.sub.3-C.sub.6)cycloalkenyloxy, (C.sub.3-C.sub.6)cycloalkyl,
(C.sub.3-C.sub.6)cycloalkoxy, halo, halo(C.sub.1-C.sub.6)alkyl, or
heterocyclyl; Optionally, R4 and R2 are joined together to form a
4-, 5-, or 6-membered ring with --(CH.sub.2)--; R5 is NO.sub.2, CN,
CO.sub.2R.sub.6, unsubstituted heterocyclyl, substituted
heterocyclyl, C(.dbd.(O or S))J(J1)(J2), wherein the substituted
heterocyclyl has one or more substituents that are independently
selected from (C.sub.2-C.sub.6)alkenyl,
(C.sub.2-C.sub.6)alkenyloxy, (C.sub.1-C.sub.6)alkoxy,
(C.sub.1-C.sub.6)alkyl, (C.sub.2-C.sub.6)alkynyl,
(C.sub.2-C.sub.6)alkynyloxy, aryl, aryl(C.sub.1-C.sub.6)alkyl,
(C.sub.3-C.sub.6)cycloalkenyl, (C.sub.3-C.sub.6)cycloalkenyloxy,
(C.sub.3-C.sub.6)cycloalkyl, (C.sub.3-C.sub.6)cycloalkoxy, halo,
halo(C.sub.1-C.sub.6)alkyl, heterocyclyl, and wherein J is N or
C(J3), and wherein J1, J2, and J3, are independently selected from
(C.sub.2-C.sub.6)alkenyl, (C.sub.2-C.sub.6)alkenyloxy,
(C.sub.2-C.sub.6)alkenylthio, (C.sub.1-C.sub.6)alkoxy,
(C.sub.1-C.sub.6)alkyl, (C.sub.1-C.sub.6)alkylthio,
(C.sub.2-C.sub.6)alkynyl, (C.sub.2-C.sub.6)alkynyloxy,
(C.sub.2-C.sub.6)alkynylthio, aryl, (C.sub.3-C.sub.6)cycloalkenyl,
(C.sub.3-C.sub.6)cycloalkenyloxy,
(C.sub.3-C.sub.6)cycloalkenylthio, (C.sub.3-C.sub.6)cycloalkyl,
(C.sub.3-C.sub.6)cycloalkoxy, (C.sub.3-C.sub.6)cycloalkylthio, H,
heterocyclyl, or (C.sub.0-C.sub.6)alkyl-C(.dbd.O)O(J4), wherein
each of which may be independently substituted (except for H) with
one or more of the following substituents, F, Cl, Br, I, CN,
NO.sub.2, (C.sub.1-C.sub.6)alkyl, (C.sub.2-C.sub.6)alkenyl,
(C.sub.2-C.sub.6)alkynyl, (C.sub.1-C.sub.6)alkoxy,
(C.sub.1-C.sub.6)haloalkyl, (C.sub.1-C.sub.6)haloalkoxy,
halo(C.sub.1-C.sub.6)alkylthio, S(.dbd.O).sub.n1(C1-C.sub.6)alkyl
(where n1=0-2), S(.dbd.O).sub.n2 halo(C.sub.1-C.sub.6)alkyl (where
n2=0-2), OSO.sub.2halo(C1-C.sub.6)alkyl,
C(.dbd.O)O(C.sub.1-C.sub.6)alkyl, C(.dbd.O)(C.sub.1-C.sub.6)alkyl,
C(.dbd.O)halo(C.sub.1-C.sub.6)alkyl, aryl,
hydroxy(C.sub.1-C.sub.6)alkyl, N(J5)(J6), and heterocyclyl, and
wherein J1 and J2 may also form a 4-, 5-, or 6-membered ring, and
wherein J4, J5, and J6 are independently selected from
(C.sub.2-C.sub.6)alkenyl, (C.sub.2-C.sub.6)alkenyloxy,
(C.sub.2-C.sub.6)alkenylthio, (C.sub.1-C.sub.6)alkoxy,
(C.sub.1-C.sub.6)alkyl, (C.sub.1-C.sub.6)alkylthio,
(C.sub.2-C.sub.6)alkynyl, (C.sub.2-C.sub.6)alkynyloxy,
(C.sub.2-C.sub.6)alkynylthio, aryl, (C.sub.3-C.sub.6)cycloalkenyl,
(C.sub.3-C.sub.6)cycloalkenyloxy,
(C.sub.3-C.sub.6)cycloalkenylthio, (C.sub.3-C.sub.6)cycloalkyl,
(C.sub.3-C.sub.6)cycloalkoxy, (C.sub.3-C.sub.6)cycloalkylthio, H,
or heterocyclyl, and wherein R6=(C.sub.1-C.sub.3)alkyl; and n is 0,
1, 2, or 3; to a locus to control said pests, in an amount to
control said pests.
2. A composition according to claim 1 wherein R1 is
##STR00021##
3. A process according to claim 1 wherein said compound is
##STR00022##
5. A process according to claim 1 wherein said compound is
##STR00023##
6. A process according to claim 1 wherein said compound is
##STR00024##
7. A process according to claim 1 wherein said compound said R1 is
a substituted pyrimidinyl, pyridazinyl, or pyrazinyl, wherein each
substituted pyrimidinyl, pyridazinyl, or pyrazinyl, has one or more
substituents independently selected from halo and
halo(C.sub.1-C.sub.6)alkyl.
8. A process according to claim 1 wherein said compound said R2 is
H or (C.sub.1-C.sub.6)alkyl.
9. A process according to claim 1 wherein said compound said R3 is
H or (C.sub.1-C.sub.6)alkyl.
10. A process according to claim 1 wherein said compound said R4 is
H or (C.sub.1-C.sub.6)alkyl.
11. A process according to claim 1 wherein said compound said R5 is
NO.sub.2 or CN.
12. A process according to claim 1 wherein said compound said R1 is
a substituted pyrimidinyl, pyridazinyl, or pyrazinyl, wherein each
substituted pyrimidinyl, pyridazinyl, or pyrazinyl, has one or more
substituents independently selected from halo and
halo(C.sub.1-C.sub.6)alkyl; R2 is H or (C.sub.1-C.sub.6)alkyl; R3
is H or (C.sub.1-C.sub.6)alkyl; R4 is H or (C.sub.1-C.sub.6)alkyl;
R5 is NO.sub.2 or CN; and n is 0, 1, 2, or 3.
Description
FIELD OF THE INVENTION
[0001] This application claims the benefit of U.S. Provisional
Application Ser. No. 61/092,077 filed on Aug. 27, 2008. This
application also claims benefit of U.S. non-provisional application
Ser. No. 12/547,049 filed on Aug. 25, 2009. The entire disclosures
of both of these applications is hereby incorporated into this
application. The invention disclosed in this document is related to
the field of pesticides and their use in controlling pests.
BACKGROUND OF THE INVENTION
[0002] Pests cause millions of human deaths around the world each
year. Furthermore, there are more than ten thousand species of
pests that cause losses in agriculture. These agricultural losses
amount to billions of U.S. dollars each year. Termites cause damage
to various structures such as homes. These termite damage losses
amount to billions of U.S. dollars each year. As a final note, many
stored food pests eat and adulterate stored food. These stored food
losses amount to billions of U.S. dollars each year, but more
importantly, deprive people of needed food.
[0003] There is an acute need for new pesticides. Insects are
developing resistance to pesticides in current use. Hundreds of
insect species are resistant to one or more pesticides. The
development of resistance to some of the older pesticides, such as
DDT, the carbamates, and the organophosphates, is well known, but
resistance has even developed to some of the newer pesticides.
Therefore, a need exists for new pesticides and particularly for
pesticides that have new modes of action.
SUBSTITUENTS (NON-EXHAUSTIVE LIST)
[0004] The examples given for the substituents are (except for
halo) non-exhaustive and must not be construed as limiting the
invention disclosed in this document.
[0005] "alkenyl" means an acyclic, unsaturated (at least one
carbon-carbon double bond), branched or unbranched, substituent
consisting of carbon and hydrogen, for example, vinyl, allyl,
butenyl, pentenyl, hexenyl, heptenyl, octenyl, nonenyl, and
decenyl.
[0006] "alkenyloxy" means an alkenyl further consisting of a
carbon-oxygen single bond, for example, allyloxy, butenyloxy,
pentenyloxy, hexenyloxy, heptenyloxy, octenyloxy, nonenyloxy, and
decenyloxy.
[0007] "alkoxy" means an alkyl further consisting of a
carbon-oxygen single bond, for example, methoxy, ethoxy, propoxy,
isopropoxy, 1-butoxy, 2-butoxy, isobutoxy, tert-butoxy, pentoxy,
2-methylbutoxy, 1,1-dimethylpropoxy, hexoxy, heptoxy, octoxy,
nonoxy, and decoxy.
[0008] "alkyl" means an acyclic, saturated, branched or unbranched,
substituent consisting of carbon and hydrogen, for example, methyl,
ethyl, propyl, isopropyl, 1-butyl, 2-butyl, isobutyl, tert-butyl,
pentyl, 2-methylbutyl, 1,1-dimethylpropyl, hexyl, heptyl, octyl,
nonyl, and decyl.
[0009] "alkynyl" means an acyclic, unsaturated (at least one
carbon-carbon triple bond, and any double bonds), branched or
unbranched, substituent consisting of carbon and hydrogen, for
example, ethynyl, propargyl, butynyl, pentynyl, hexynyl, heptynyl,
octynyl, nonynyl, and decynyl.
[0010] "alkynyloxy" means an alkynyl further consisting of a
carbon-oxygen single bond, for example, pentynyloxy, hexynyloxy,
heptynyloxy, octynyloxy, nonynyloxy, and decynyloxy.
[0011] "aryl" means a cyclic, aromatic substituent consisting of
hydrogen and carbon, for example, phenyl, naphthyl, and
biphenylyl.
[0012] "cycloalkenyl" means a monocyclic or polycyclic, unsaturated
(at least one carbon-carbon double bond) substituent consisting of
carbon and hydrogen, for example, cyclobutenyl, cyclopentenyl,
cyclohexenyl, cycloheptenyl, cyclooctenyl, cyclodecenyl,
norbornenyl, bicyclo[2.2.2]octenyl, tetrahydronaphthyl,
hexahydronaphthyl, and octahydronaphthyl.
[0013] "cycloalkenyloxy" means a cycloalkenyl further consisting of
a carbon-oxygen single bond, for example, cyclobutenyloxy,
cyclopentenyloxy, cyclohexenyloxy, cycloheptenyloxy,
cyclooctenyloxy, cyclodecenyloxy, norbornenyloxy, and
bicyclo[2.2.2]octenyloxy.
[0014] "cycloalkyl" means a monocyclic or polycyclic, saturated
substituent consisting of carbon and hydrogen, for example,
cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl,
cyclooctyl, cyclodecyl, norbornyl, bicyclo[2.2.2]octyl, and
decahydronaphthyl.
[0015] "cycloalkoxy" means a cycloalkyl further consisting of a
carbon-oxygen single bond, for example, cyclopropyloxy,
cyclobutyloxy, cyclopentyloxy, cyclohexyloxy, cycloheptyloxy,
cyclooctyloxy, cyclodecyloxy, norbornyloxy, and
bicyclo[2.2.2]octyloxy.
[0016] "halo" means fluoro, chloro, bromo, and iodo.
[0017] "haloalkyl" means an alkyl further consisting of, from one
to the maximum possible number of, identical or different, halos,
for example, fluoromethyl, difluoromethyl, trifluoromethyl,
1-fluoromethyl, 2-fluoroethyl, 2,2,2-trifluoroethyl, chloromethyl,
trichloromethyl, and 1,1,2,2-tetrafluoroethyl.
[0018] "heterocyclyl" means a cyclic substituent that may be fully
saturated, partially unsaturated, or fully unsaturated, where the
cyclic structure contains at least one carbon and at least one
heteroatom, where said heteroatom is nitrogen, sulfur, or oxygen,
for example, benzofuranyl, benzoisothiazolyl, benzoisoxazolyl,
benzoxazolyl, benzothienyl, benzothiazolyl cinnolinyl, furanyl,
indazolyl, indolyl, imidazolyl, isoindolyl, isoquinolinyl,
isothiazolyl, isoxazolyl, 1,3,4-oxadiazolyl, oxazolinyl, oxazolyl,
phthalazinyl, pyrazinyl, pyrazolinyl, pyrazolyl, pyridazinyl,
pyridyl, pyrimidinyl, pyrrolyl, quinazolinyl, quinolinyl,
quinoxalinyl, 1,2,3,4-tetrazolyl, thiazolinyl, thiazolyl, thienyl,
1,2,3-triazinyl, 1,2,4-triazinyl, 1,3,5-triazinyl, 1,2,3-triazolyl,
and 1,2,4-triazolyl.
DETAILED DESCRIPTION OF THE INVENTION
[0019] The pesticidal compositions of this invention comprise a
molecule having the following general formula:
##STR00001##
[0020] wherein
[0021] R1 is [0022] (a) an unsubstituted pyrimidinyl, pyridazinyl,
or pyrazinyl, or [0023] (b) a substituted pyrimidinyl, pyridazinyl
or pyrazinyl, wherein each substituted pyrimidinyl, pyridazinyl, or
pyrazinyl, has one or more substituents independently selected from
(C.sub.2-C.sub.6)alkenyl, (C.sub.2-C.sub.6)alkenyloxy,
(C.sub.1-C.sub.6)alkoxy, (C.sub.1-C.sub.6)alkyl,
(C.sub.2-C.sub.6)alkynyl, (C.sub.2-C.sub.6)alkynyloxy, aryl,
(C.sub.3-C.sub.6)cycloalkenyl, (C.sub.3-C.sub.6)cycloalkenyloxy,
(C.sub.3-C.sub.6)cycloalkyl, (C.sub.3-C.sub.6)cycloalkoxy, halo,
halo(C.sub.1-C.sub.6)alkyl, or heterocyclyl;
[0024] R2 is H, (C.sub.2-C.sub.6)alkenyl,
(C.sub.2-C.sub.6)alkenyloxy, (C.sub.1-C.sub.6)alkoxy,
(C.sub.1-C.sub.6)alkyl, (C.sub.2-C.sub.6)alkynyl,
(C.sub.2-C.sub.6)alkynyloxy, aryl, (C.sub.3-C.sub.6)cycloalkenyl,
(C.sub.3-C.sub.6)cycloalkenyloxy, (C.sub.3-C.sub.6)cycloalkyl,
(C.sub.3-C.sub.6)cycloalkoxy, halo, halo(C.sub.1-C.sub.6)alkyl, or
heterocyclyl;
[0025] R3 is H, (C.sub.2-C.sub.6)alkenyl,
(C.sub.2-C.sub.6)alkenyloxy, (C.sub.1-C.sub.6)alkoxy,
(C.sub.1-C.sub.6)alkyl, (C.sub.2-C.sub.6)alkynyl,
(C.sub.2-C.sub.6)alkynyloxy, aryl, (C.sub.3-C.sub.6)cycloalkenyl,
(C.sub.3-C.sub.6)cycloalkenyloxy, (C.sub.3-C.sub.6)cycloalkyl,
(C.sub.3-C.sub.6)cycloalkoxy, halo, halo(C.sub.1-C.sub.6)alkyl, or
heterocyclyl;
[0026] Optionally, R2 and R3 may form a ring wherein the ring
contains 3 or more ring atoms optionally containing an O, S, or N
atom;
[0027] R4 is H, (C.sub.2-C.sub.6)alkenyl,
(C.sub.2-C.sub.6)alkenyloxy, (C.sub.1-C.sub.6)alkoxy,
(C.sub.1-C.sub.6)alkyl, (C.sub.2-C.sub.6)alkynyl,
(C.sub.2-C.sub.6)alkynyloxy, aryl, (C.sub.3-C.sub.6)cycloalkenyl,
(C.sub.3-C.sub.6)cycloalkenyloxy, (C.sub.3-C.sub.6)cycloalkyl,
(C.sub.3-C.sub.6)cycloalkoxy, halo, halo(C.sub.1-C.sub.6)alkyl, or
heterocyclyl;
[0028] Optionally, R4 and R2 are joined together to form a 4-, 5-,
or 6-membered ring with --(CH.sub.2)--;
[0029] R5 is NO.sub.2, CN, CO.sub.2R.sub.6, unsubstituted
heterocyclyl, substituted heterocyclyl, C(.dbd.(O or
S))J(J1)(J2),
[0030] wherein the substituted heterocyclyl has one or more
substituents that are independently selected from
(C.sub.2-C.sub.6)alkenyl, (C.sub.2-C.sub.6)alkenyloxy,
(C.sub.1-C.sub.6)alkoxy, (C.sub.1-C.sub.6)alkyl,
(C.sub.2-C.sub.6)alkynyl, (C.sub.2-C.sub.6)alkynyloxy, aryl,
aryl(C.sub.1-C.sub.6)alkyl, (C.sub.3-C.sub.6)cycloalkenyl,
(C.sub.3-C.sub.6)cycloalkenyloxy, (C.sub.3-C.sub.6)cycloalkyl,
(C.sub.3-C.sub.6)cycloalkoxy, halo, halo(C.sub.1-C.sub.6)alkyl,
heterocyclyl, and
[0031] wherein J is N or C(J3), and
[0032] wherein J1, J2, and J3, are independently selected from
(C.sub.2-C.sub.6)alkenyl, (C.sub.2-C.sub.6)alkenyloxy,
(C.sub.2-C.sub.6)alkenylthio, (C.sub.1-C.sub.6)alkoxy,
(C.sub.1-C.sub.6)alkyl, (C.sub.1-C.sub.6)alkylthio,
(C.sub.2-C.sub.6)alkynyl, (C.sub.2-C.sub.6)alkynyloxy,
(C.sub.2-C.sub.6)alkynylthio, aryl, (C.sub.3-C.sub.6)cycloalkenyl,
(C.sub.3-C.sub.6)cycloalkenyloxy,
(C.sub.3-C.sub.6)cycloalkenylthio, (C.sub.3-C.sub.6)cycloalkyl,
(C.sub.3-C.sub.6)cycloalkoxy, (C.sub.3-C.sub.6)cycloalkylthio, H,
heterocyclyl, or (C.sub.0-C.sub.6)alkyl-C(.dbd.O)O(J4), wherein
each of which may be independently substituted (except for H) with
one or more of the following substituents, F, Cl, Br, I, CN,
NO.sub.2, (C.sub.1-C.sub.6)alkyl, (C.sub.2-C.sub.6)alkenyl,
(C.sub.2-C.sub.6)alkynyl, (C.sub.1-C.sub.6)alkoxy,
(C.sub.1-C.sub.6)haloalkyl, (C.sub.1-C.sub.6)haloalkoxy,
halo(C.sub.1-C.sub.6)alkylthio, S(.dbd.O).sub.n1(C1-C.sub.6)alkyl
(where n1=0-2), S(.dbd.O).sub.n2 halo(C.sub.1-C.sub.6)alkyl (where
n2=0-2), OSO.sub.2halo(C1-C.sub.6)alkyl,
C(.dbd.O)O(C.sub.1-C.sub.6)alkyl, C(.dbd.O)(C.sub.1-C.sub.6)alkyl,
C(.dbd.O)halo(C.sub.1-C.sub.6)alkyl, aryl,
hydroxy(C.sub.1-C.sub.6)alkyl, N(J5)(J6), and heterocyclyl, and
[0033] wherein J1 and J2 may also form a 4-, 5-, or 6-membered
ring, and
[0034] wherein J4, J5, and J6 are independently selected from
(C.sub.2-C.sub.6)alkenyl, (C.sub.2-C.sub.6)alkenyloxy,
(C.sub.2-C.sub.6)alkenylthio, (C.sub.1-C.sub.6)alkoxy,
(C.sub.1-C.sub.6)alkyl, (C.sub.1-C.sub.6)alkylthio,
(C.sub.2-C.sub.6)alkynyl, (C.sub.2-C.sub.6)alkynyloxy,
(C.sub.2-C.sub.6)alkynylthio, aryl, (C.sub.3-C.sub.6)cycloalkenyl,
(C.sub.3-C.sub.6)cycloalkenyloxy,
(C.sub.3-C.sub.6)cycloalkenylthio, (C.sub.3-C.sub.6)cycloalkyl,
(C.sub.3-C.sub.6)cycloalkoxy, (C.sub.3-C.sub.6)cycloalkylthio, H,
or heterocyclyl, and
[0035] wherein R6=(C.sub.1-C.sub.3)alkyl; and
[0036] n is 0, 1, 2, or 3.
[0037] In another embodiment of the invention, R1 is
##STR00002##
[0038] Procedures known in the art can be used to make the
molecules herein, In general, these molecules can be made as
follows.
[0039] The compounds of formula (1a), wherein R.sup.5 represents CN
and R.sup.1, R.sup.2, R.sup.3, R.sup.4 are as previously defined,
can be prepared by the method illustrated in Scheme A. The
methylene carbon adjacent to the heterocyclic ring R.sup.1 is first
halogenated using N-bromosuccinimide, N-chlorosuccinimide, or
trichloroisocyanuric acid. The sulfide is prepared by nucleophilic
substitution of the halide with the sodium salt of an alkyl thiol.
The sulfide is oxidized with iodobenzene diacetate in the presence
of cyanamide at 0.degree. C. to give the sulfilimine. The reaction
can be carried out in a polar aprotic solvent like dichloromethane
(CH.sub.2Cl.sub.2). The sulfilimine is then oxidized with
meta-chloroperoxybenzoic acid (mCPBA). A base such as potassium
carbonate is employed to neutralize the acidity of mCPBA. Protic
polar solvents such as ethanol and water are used to increase the
solubility of the sulfilimine starting material and the base
employed. The sulfilimine can also be oxidized with aqueous sodium
or potassium periodate solution in the presence of a catalyst such
as ruthenium trichloride hydrate or similar. The organic solvent
for this catalysis can be a polar aprotic solvent such as
CH.sub.2Cl.sub.2, chloroform, or acetonitrile.
##STR00003##
[0040] The compounds of formula (1b), wherein R.sup.1, R.sup.2,
R.sup.3, R.sup.4, are as previously defined and R.sup.5 is CN,
NO.sub.2, or CO.sub.2R.sub.6, can be prepared from the sulfide by
the methods illustrated in Scheme B. The sulfide is oxidized with
mCPBA in a polar solvent below 0.degree. C. to provide the
sulfoxide. In most cases, CH.sub.2Cl.sub.2 is a preferred solvent
for oxidation. The sulfoxide is then iminated with sodium azide in
the presence of concentrated sulfuric acid in an aprotic solvent
under heating to provide the sulfoximine. In most cases, chloroform
is a preferred solvent for this reaction. The nitrogen of the
sulfoximine can be either cyanated with cyanogen bromide in the
presence of a base, nitrated with nitric acid in the presence of
acetic anhydride under mildly elevated temperature, or carboxylated
with an alkyl (R.sup.6) chloroformate in the presence of a base
such as 4-dimethylaminopyridine (DMAP) to provide the N-substituted
sulfoximine. Base is required for efficient cyanation and
carboxylation and the preferred base is DMAP, whereas sulfuric acid
is used as a catalyst for efficient nitration reaction.
##STR00004##
[0041] The compounds of formula (1c), wherein R.sup.1, R.sup.2,
R.sup.3, R.sup.4, are as previously defined and R.sup.5 is thiourea
(--C(S)NH.sub.2), can be prepared from the unsubstituted (N--H)
sulfoximine by the methods illustrated in Scheme C. The sulfoximine
nitrogen is reacted with Fmoc-isothiocyanate
(Fmoc=9-fluorenylmethoxycarbonyl) to furnish the Fmoc-protected
thiourea. Deprotection of the thiourea can be achieved through
treatment with a base such as piperidine in a solvent such as
N,N-dimethylformamide (DMF).
##STR00005##
[0042] The compounds of formula (1d), wherein R.sup.1, R.sup.2,
R.sup.3, R.sup.4, are as previously defined and R.sup.5 is a
substituted or unsubstituted thiazole, can be prepared from the
thiourea-substituted sulfoximine (1c) by the method illustrated in
Scheme D. Reaction of (1c) with a suitably substituted
.alpha.-bromoketone or .alpha.-bromoaldehyde (where R.sup.7 and
R.sup.8 are independently H, alkyl, haloalkyl, substituted or
unsubstituted aryl, or aryl(C.sub.1-C.sub.6)alkyl) furnishes the
N-thiazolyl sulfoximine (1d).
##STR00006##
[0043] The .alpha.-carbon of the N-substituted sulfoximine, where,
R.sup.2 and R.sup.3.dbd.H and R.sup.1, R.sup.4 and R.sup.5 are as
previously defined, can be further alkylated or halogenated (R2) in
the presence of a base such as potassium hexamethyldisilazide
(KHMDS) to give N-substituted sulfoximines of formula (1e), wherein
R.sup.1, R.sup.4, R.sup.5 are as previously defined and Z is an
appropriate leaving group, as illustrated in Scheme E. The
preferred leaving groups are iodide (R2=alkyl), benzenesulfonimide
(R2=F), tetrachloroethene (R2=Cl), and tetrafluoroethene
(R2=Br).
##STR00007##
[0044] In Scheme F, the sulfide of formula (A.sub.1) can be
prepared from the corresponding substituted chloromethyl
heterocyclyl by treatment with thiourea, hydrolysis and subsequent
alkylation with the appropriate bromo chloroalkane (m=0, 1, or 2)
under aqueous base conditions, and cyclization in the presence of a
base like potassium-t-butoxide in a polar aprotic solvent such as
tetrahydrofuran (THF).
##STR00008##
[0045] Sulfoximine compounds of the formula (1f) wherein n=2,
R.sup.2 and R.sup.3 are hydrogen and R.sup.1, R.sup.4 and R.sup.5
are as previously defined, can be prepared by the method
illustrated in Scheme G. Dimethylsulfide is oxidized with
iodobenzene diacetate in the presence of cyanamide at 0.degree. C.
to give the corresponding sulfilimine. The reaction can be carried
out in a polar aprotic solvent like CH.sub.2Cl.sub.2 or THF. The
sulfilimine is then oxidized with mCPBA. A base such as potassium
carbonate is employed to neutralize the acidity of mCPBA. Protic
polar solvents such as ethanol and water are used to increase the
solubility of the sulfilimine starting material and the base
employed. The a-carbon of the N-substituted sulfoximine can be
alkylated with a heteroaromatic methyl halide in the presence of a
base such as KHMDS or butyl lithium (nBuLi) to give the desired
N-substituted sulfoximine. The preferred halide can be bromide,
chloride or iodide.
##STR00009##
[0046] Sulfide compounds of the formula (A.sub.2) can be prepared
by the method illustrated in Scheme H. 2-Ethoxymethylene-malonic
acid diethyl ester is reacted with trifluoroacetamidine to form a
pyrimidinone, which can then be chlorinated with oxalyl chloride.
The chloropyrimidine can be reduced using hydrogen and a palladium
on carbon catalyst to give the corresponding pyrimidine. The ester
can then be reduced to the aldehyde using diisobutylaluminum
hydride (DIBAL-H) which can then be alkylated with a Grignard
reagent (R.sub.2MgBr). The resulting alcohol can be chlorinated
using thionyl chloride, and then nucleophilic substitution of the
halide with the sodium salt of an alkyl thiol will furnish the
desired sulfide.
##STR00010##
EXAMPLES
[0047] The examples are for illustration purposes and are not to be
construed as limiting the invention disclosed in this document to
only the embodiments disclosed in these examples.
Example I
Preparation of
[1-(2-chloropyrimidin-5-yl)ethyl](methyl)oxido-.lamda..sup.4-sulfanyliden-
ecyanamide (1)
##STR00011##
[0049] A solution of 2-chloro-5-ethylpyrimidine (1.15 g, 8.1 mmol)
in 20 mL of carbon tetrachloride was treated with
N-bromosuccinimide (1.50 g, 8.4 mmol) and a catalytic amount (about
1 mol percent based on reactants) of benzoyl peroxide and then
heated to 75.degree. C. After several hours and additional
catalyst, the starting material was completely consumed. The solids
were removed and the filtrate was concentrated. The resulting
residue was further purified by flash column chromatography on
silica gel using a mixture of ethyl acetate (EtOAc) and petroleum
ether as the eluant. The solvents were removed under reduced
pressure to yield 0.64 g (36%) of
5-(1-bromoethyl)-2-chloropyrimidine (A) as a clear liquid: .sup.1H
NMR (CDCl.sub.3) .delta. 8.70 (s, 2H), 5.15 (q, J=8.0 Hz, 1H), 2.10
(d, J=8.0 Hz, 3H); GCMS (FID) m/z 222 (M+). Some of the
corresponding dibromo compound 0.44 g (18%) was also isolated, as a
white solid: mp 84-85.degree. C.; .sup.1H NMR (CDCl.sub.3) d 9.00
(s, 2H), 3.00 (s, 3H); LC-MS (ESIMS) m/z 298 (M+H).
##STR00012##
[0050] A suspension of sodium methylthiolate (245 mg, 3.50 mmol) in
ethanol was treated with a solution of
5-(1-bromoethyl)-2-chloropyrimidine in ethanol at room temperature.
After 5 hours (h), the reaction was partitioned between
CH.sub.2Cl.sub.2 and dilute hydrochloric acid, washed with
saturated brine and dried over sodium sulfate (Na.sub.2SO.sub.4).
The solvent were removed under reduced pressure to yield 0.45 g
(89%) of 2-chloro-5-[1-(methylthio)ethyl]pyrimidine (B) as a pale
yellow syrup: .sup.1H NMR (CDCl.sub.3) .delta. 8.60 (s, 2H), 3.85
(q, J=8.0 Hz, 1H), 1.98 (s, 3H), 1.65 (d, J=8.0 Hz, 3H); GC-MS
(FID) m/z 188 (M+).
##STR00013##
[0051] A solution of 2-chloro-5-[1-(methylthio)ethyl]pyrimidine
(0.49 g, 2.61 mmol) and cyanamide (120 mg, 2.86 mmol) in 20 mL of
CH.sub.2Cl.sub.2 was cooled to 0.degree. C. and treated with
iodobenzene diacetate (860 mg, 2.59 mmol). The mixture was allowed
to warm to room temperature over an hour, the solvent was removed
under reduced pressure and the residue was partitioned between
hexanes and acetonitrile. The acetonitrile was removed under
reduced pressure and the residue was further purified by flash
column chromatography on silica gel using a 50% mixture of acetone
and petroleum ether as the eluant. The solvents were removed under
reduced pressure to yield 0.44 g (74%) of
(1E)-[1-(2-chloropyrimidin-5-yl)ethyl](methyl)-.lamda..sup.4-sulfanyliden-
ecyanamide (C) as a pale orange syrup. This material was a 2:1
mixture of diastereomers. The physical properties of the major
diastereomer were: .sup.1H NMR (CDCl.sub.3) .delta. 8.68 (s, 2H),
4.38 (q, J=8.3 Hz, 1H), 2.68 (s, 3H), 1.92 (d, J=8.3 Hz, 3H); LC-MS
(ESI) m/z 229 (M+H).
##STR00014##
[0052] A rapidly stirring mixture of sodium periodate (458 mg, 2.14
mmol) in 10 mL of a 1:1 mixture of water (H.sub.2O) and
CH.sub.2Cl.sub.2 was first treated with ruthenium(III) chloride
hydrate (13 mg, 0.06 mmol) and then a solution of
(1E)-[1-(2-chloropyrimidin-5-yl)ethyl](methyl)-.lamda..sup.4-sulfanyliden-
ecyanamide (242 mg, 1.06 mmol) in 7 mL of CH.sub.2Cl.sub.2 added
dropwise over 15 min. The mixture was stirred for 18 h at room
temperature. The dark mixture was then partitioned between
CH.sub.2Cl.sub.2 and dilute hydrochloric acid, and the organic
layer was dried over Na.sub.2SO.sub.4. The solvent was removed
under reduced pressure, and the residue was taken up in acetone and
passed through a plug of alumina. The acetone was removed under
reduced pressure to yield 122 mg (50%) of
[1-(2-chloropyrimidin-5-yl)ethyl](methyl)oxido-.lamda..sup.4-sulfanyliden-
ecyanamide (1) as a clear syrup. This material was a 2:1 mixture of
diastereomers. The physical properties of the major diastereomer
were: .sup.1H NMR (CDCl.sub.3) .delta. 8.68 (s, 2H), 4.52 (q, J=9
Hz, 1H), 3.10 (s, 3H), 1.95 (d, J=9 Hz, 3H); LC-MS (ESI) m/z 245
(M+H).
Example II
Preparation of
[(3-chloropyridazin-6-yl)methyl](methyl)oxido-.lamda..sup.4-sulfanylidene-
cyanamide (2)
##STR00015##
[0054] To a refluxing solution of 3-chloro-6-methylpyridazine (5.0
g, 39 mmol) in chloroform (75 mL) was added trichloroisocyanuric
acid (3.6 g, 16 mmol) portionwise. The solution was allowed to
reflux overnight, after which the crude reaction mixture was
filtered, washed with 1 M sodium hydroxide (NaOH), and the organic
phase was dried over magnesium sulfate. The crude product was
concentrated under reduced pressure and purified by silica gel
chromatography to furnish 3-chloro-6-chloromethyl-pyridazine (D) as
a yellow oil which upon sitting became a brown solid=2.9 g
(46%).
##STR00016##
[(3-Chloropyridazin-6-yl)methyl](methyl)oxido-.lamda..sup.4-sulfanylidene-
cyanamide (2) was synthesized from
3-chloro-6-chloromethyl-pyridazine (D) using the synthetic
procedure provided in Example I. The desired product was isolated
as a yellow solid: .sup.1H NMR (CDCl.sub.3) .delta. 7.3 (d, J=7.5
Hz, 1H), 7.2 (d, J=7.5 Hz, 1H) 4.8 (m, 2H), 2.8 (s, 3H); LC-MS
(ESI) m/z 230 (M+).
Example III
Preparation of
methyl(oxido){1-[2-(trifluoromethyl)pyrimidin-5-yl]ethyl}-.lamda..sup.4-s-
ulfanylidenecyanamide (3)
##STR00017##
[0056] To a magnetically stirred solution of methyl Grignard (19.9
mL of a 3 M solution in ether (Et.sub.2O), 59.7 mmol) in Et.sub.2O
(167 mL) was added a solution of
2-trifluoromethylpyrimidine-5-carbaldehyde* (9.56 g, 54.3 mmol) in
Et.sub.2O (50 mL) at 0.degree. C., and the resulting pale yellow
solution was warmed to room temperature (RT) and stirred for 2.5 h.
The reaction was quenched by the addition of saturated aqueous
ammonium chloride (NH.sub.4Cl) (50 mL) at 0.degree. C., and the
mixture was warmed to RT. The phases were separated and the organic
phase was dried over Na.sub.2SO.sub.4, filtered, and concentrated
to give a light yellow oil (9.32 g crude). The oil was purified by
flash chromatography (330 g SiO.sub.2, 0.fwdarw.100% EtOAc/hexanes
gradient) to give 1-(2-trifluoromethylpyrimidin-5-yl)ethanol (E)
(8.87 g, 85%) as a light yellow solid: mp 43-45.degree. C.; .sup.1H
NMR (300 MHz, CDCl.sub.3) .delta. 8.92 (s, 2H), 5.15-5.07 (m, 1H),
2.26 (d, J=4.0 Hz, 1H), 1.62 (d, J=6.5 Hz, 3H); MS (EI) m/z 192
(M).sup.+.
[0057] *2-Trifluoromethylpyrimidine-5-carbaldehyde can be prepared
in four steps through methods known in the literature. [0058] 1)
Fenwick, A. E.; Hickey, D. M. B.; Ife, R. J.; Leach, C. A.; Pinto,
I. L.; Smith, S. A. (SmithKline Beecham PLC, UK). WO 200066567,
Nov. 9, 2000. [0059] 2) Hickey, D. M. B.; Ife, R. J.; Leach, C. A.;
Smith, S. A. (SmithKline Beecham PLC, UK). WO 200066566, Nov. 9,
2000.
[0059] ##STR00018## [0060] A) To a magnetically stirred solution of
1-(2-trifluoromethylpyrimidin-5-yl)ethanol (E; 5.00 g, 26.0 mmol)
in anhydrous acetonitrile (17 mL) was added thionyl chloride (3.87
g, 32.5 mmol) at 0.degree. C. The ice bath was removed and the
resulting light yellow solution was stirred for 1 h. The reaction
was analyzed by GC-MS, which confirmed full conversion of the
starting material (SM) to the desired
5-(1-chloroethyl)-2-trifluoromethylpyrimidine intermediate ((EI)
m/z 210 (M).sup.+). The solvent and excess thionyl chloride were
removed on the rotary evaporator, and the residual amber oil was
dissolved in anhydrous acetonitrile (20 mL) and used without
further purification. [0061] B) The solution of
5-(1-chloroethyl)-2-trifluoromethylpyrimidine (F) was cooled to
0.degree. C., and sodium thiomethoxide (2.96 g, 42.3 mmol) was
added in portions (3.times.0.99 g) over 5 minutes (min). The ice
bath was removed and the resulting orange mixture was warmed to RT
and stirred for 1 h. The reaction was diluted with brine (100 mL)
and extracted with Et.sub.2O (3.times.150 mL). The organic extracts
were combined, dried over Na.sub.2SO.sub.4, filtered, and
concentrated to give an amber oil (5.21 g crude). The oil was
purified by flash chromatography (330 g SiO.sub.2, 0.fwdarw.100%
EtOAc/hexanes gradient) to give
5-(1-methylsulfonylethyl)-2-trifluoromethylpyrimidine (G; 4.16 g,
72%) as a yellow oil: .sup.1H NMR (300 MHz, CDCl.sub.3) .delta.
8.86 (s, 2H), 3.92 (q, J=7.3, 1H), 1.98 (s, 3H), 1.68 (d, J=7.2,
3H); MS (EI) m/z 222 (M).sup.+.
[0061] ##STR00019## [0062] A) To a magnetically stirred solution of
5-(1-methylsulfonylethyl)-2-trifluoromethylpyrimidine (G; 0.50 g,
2.60 mmol) and cyanamide (0.114 g, 2.73 mmol) in anhydrous
acetonitrile (5.2 mL) was added iodobenzenediacetate (0.924 g, 2.87
mmol) at 0.degree. C. under nitrogen (N.sub.2). The ice bath was
removed, the pale yellow mixture was warmed to RT and the resulting
orange solution was stirred for 16 h. The reaction was analyzed by
LC-MS, which confirmed the formation of
methyl{1-[2-(trifluoromethyl)pyrimidin-5-yl]ethyl}-.lamda..sup.4-sulfanyl-
idenecyanamide (H) ((ESI) m/z 263 [M+H].sup.+, 261 [M-H].sup.-).
The solution was washed with hexanes (5.times.10 mL), and the
acetonitrile was removed on the rotary evaporator to give an orange
oil which was dissolved in CH.sub.2Cl.sub.2 (26 mL) and used
without further purification. [0063] B) To a magnetically stirred
solution of
methyl{1-[2-(trifluoromethyl)pyrimidin-5-yl]ethyl}-.lamda..sup.4-sulfanyl-
idenecyanamide (H; 0.68 g, 2.60 mmol) in CH.sub.2Cl.sub.2 (26 mL)
was slowly added aqueous sodium permanganate (NaMnO.sub.4) (0.92 g
of 40%, 2.60 mmol) at 0.degree. C. The ice bath was removed and the
resulting dark mixture was warmed to RT and stirred for 1.5 h. The
reaction was washed with aqueous sodium bisulfite, and the entire
mixture was filtered. The phases were separated and the aqueous
phase was extracted with CH.sub.2Cl.sub.2 (2.times.25 mL). The
organic phases were combined, washed with brine (25 mL), dried over
Na.sub.2SO.sub.4, filtered, and concentrated to give a white, pasty
residue (0.517 g crude). The crude material was purified by flash
chromatography (80 g SiO.sub.2, 0.fwdarw.100% acetone/Hexanes
gradient) to give a 1:1 mixture of diastereomers of
methyl(oxido){1-[2-(trifluoromethyl)pyrimidin-5-yl]ethyl}-.lamda..sup.4-s-
ulfanylidenecyanamide (I; 0.33 g, 46%) as a colorless, waxy solid:
.sup.1H NMR (300 MHz, CDCl.sub.3) .delta. 9.20 (d, J=1.3 Hz, 2H),
5.40 (q, J=7.1 Hz, 0.5H), 5.38 (q, J=7.1 Hz, 0.5H), 3.54 (s, 1.5H),
3.53 (s, 1.5H), 1.92 (d, J=7.1 Hz, 1.5H), 1.91 (d, J=7.0 Hz, 1.5H);
MS (ESIMS) m/z 279 [M+H].sup.+, m/z 277 [M-H].sup.-.
Example IV
Insecticidal Testing
[0064] The compounds identified in the foregoing examples were
tested against cotton aphid using procedures described
hereinafter.
Insecticidal Test for Cotton Aphid (Aphis gossypii) in Foliar Spray
Assay
[0065] Squash seedlings with fully expanded cotyledon leaves were
trimmed to one cotyledon per plant and infested with cotton aphid
(wingless adults and nymphs) 1 day prior to chemical application.
Each plant was examined before chemical application to ensure
uniform infestation (ca. 30-70 aphids per plant). Compounds (2 mg)
were dissolved in 2 mL of acetone/methanol (1:1) solvent, forming
stock solutions of 1000 ppm. The stock solutions were diluted
5.times. with 0.025% Tween 20 in H.sub.2O to obtain a solution at
200 ppm. A hand-held Devilbiss aspirator type sprayer was used to
apply the spray solutions until runoff to both sides of the squash
cotyledon leaves. Four plants (4 replications) were used for each
compound. Reference plants (solvent check) were sprayed with the
diluent only. Treated plants were held in a holding room for 3 days
at approximately 23.degree. C. and 40% relative humidity (RH)
before the number of live aphids on each plant was recorded.
Insecticidal activity was measured by Corrected % Control using
Abbott's correction formula and presented in Table 1-Activity:
Corrected % Control=100*(X-Y)/X [0066] where X=No. of live aphids
on solvent check plants [0067] Y=No. of live aphids on treated
plants Results are shown in Table 1.
TABLE-US-00001 [0067] TABLE 1 Activity. % Control at ppm, against
cotton aphid on squash (foliar spray) Comp # 200 ppm 1 A 2 A 3
A
In each case of Table 1 the rating scale is as follows:
TABLE-US-00002 % Control (or Mortality) Rating 80-100 A Less than
80 B Not tested C
Acid & Salt Derivatives, and Solvates
[0068] The compounds disclosed in this invention can be in the form
of pesticidally acceptable acid addition salts.
[0069] By way of non-limiting example, an amine function can form
salts with hydrochloric, hydrobromic, sulfuric, phosphoric, acetic,
benzoic, citric, malonic, salicylic, malic, fumaric, oxalic,
succinic, tartaric, lactic, gluconic, ascorbic, maleic, aspartic,
benzenesulfonic, methanesulfonic, ethanesulfonic,
hydroxymethanesulfonic, and hydroxyethanesulfonic acids.
[0070] Additionally, by way of non-limiting example, an acid
function can form salts including those derived from alkali or
alkaline earth metals and those derived from ammonia and amines.
Examples of preferred cations include sodium, potassium, magnesium,
and aminium cations.
[0071] The salts are prepared by contacting the free base form with
a sufficient amount of the desired acid to produce a salt. The free
base forms may be regenerated by treating the salt with a suitable
dilute aqueous base solution such as dilute aqueous NaOH, potassium
carbonate, ammonia, and sodium bicarbonate. As an example, in many
cases, a pesticide is modified to a more water soluble form e.g.
2,4-dichlorophenoxy acetic acid dimethyl amine salt is a more water
soluble form of 2,4-dichlorophenoxy acetic acid, a well known
herbicide.
[0072] The compounds disclosed in this invention can also form
stable complexes with solvent molecules that remain intact after
the non-complexed solvent molecules are removed from the compounds.
These complexes are often referred to as "solvates."
Stereoisomers
[0073] Certain compounds disclosed in this invention can exist as
one or more stereoisomers. The various stereoisomers include
geometric isomers, diastereomers, and enantiomers. Thus, the
compounds disclosed in this invention include racemic mixtures,
individual stereoisomers, and optically active mixtures. It will be
appreciated by those skilled in the art that one stereoisomer may
be more active than the others. Individual stereoisomers and
optically active mixtures may be obtained by selective synthetic
procedures, by conventional synthetic procedures using resolved
starting materials, or by conventional resolution procedures.
Pests
[0074] In another embodiment, the invention disclosed in this
document can be used to control pests.
[0075] In another embodiment, the invention disclosed in this
document can be used to control pests of the Phylum Nematoda.
[0076] In another embodiment, the invention disclosed in this
document can be used to control pests of the Phylum Arthropoda.
[0077] In another embodiment, the invention disclosed in this
document can be used to control pests of the Subphylum
Chelicerata.
[0078] In another embodiment, the invention disclosed in this
document can be used to control pests of the Class Arachnida.
[0079] In another embodiment, the invention disclosed in this
document can be used to control pests of the Subphylum
Myriapoda.
[0080] In another embodiment, the invention disclosed in this
document can be used to control pests of the Class Symphyla.
[0081] In another embodiment, the invention disclosed in this
document can be used to control pests of the Subphylum
Hexapoda.
[0082] In another embodiment, the invention disclosed in this
document can be used to control pests of the Class Insecta.
[0083] In another embodiment, the invention disclosed in this
document can be used to control Coleoptera (beetles). A
non-exhaustive list of these pests includes, but is not limited to,
Acanthoscelides spp. (weevils), Acanthoscelides obtectus (common
bean weevil), Agrilus planipennis (emerald ash borer), Agriotes
spp. (wireworms), Anoplophora glabripennis (Asian longhorned
beetle), Anthonomus spp. (weevils), Anthonomus grandis (boll
weevil), Aphidius spp., Apion spp. (weevils), Apogonia spp.
(grubs), Ataenius spretulus (Black Turgrass Ataenius), Atomaria
linearis (pygmy mangold beetle), Aulacophore spp., Bothynoderes
punctiventris (beet root weevil), Bruchus spp. (weevils), Bruchus
pisorum (pea weevil), Cacoesia spp., Callosobruchus maculatus
(southern cow pea weevil), Carpophilus hemipteras (dried fruit
beetle), Cassida vittata, Cerosterna spp, Cerotoma spp.
(chrysomeids), Cerotoma trifurcata (bean leaf beetle),
Ceutorhynchus spp. (weevils), Ceutorhynchus assimilis (cabbage
seedpod weevil), Ceutorhynchus napi (cabbage curculio), Chaetocnema
spp. (chrysomelids), Colaspis spp. (soil beetles), Conoderus
scalaris, Conoderus stigmosus, Conotrachelus nenuphar (plum
curculio), Cotinus nitidis (Green June beetle), Crioceris asparagi
(asparagus beetle), Cryptolestes ferrugineus (rusty grain beetle),
Cryptolestes pusillus (flat grain beetle), Cryptolestes turcicus
(Turkish grain beetle), Ctenicera spp. (wireworms), Curculio spp.
(weevils), Cyclocephala spp. (grubs), Cylindrocpturus adspersus
(sunflower stem weevil), Deporaus marginatus (mango leaf-cutting
weevil), Dermestes lardarius (larder beetle), Dermestes maculates
(hide beetle), Diabrotica spp. (chrysolemids), Epilachna varivestis
(Mexican bean beetle), Faustinus cubae, Hylobius pales (pales
weevil), Hypera spp. (weevils), Hypera postica (alfalfa weevil),
Hyperdoes spp. (Hyperodes weevil), Hypothenemus hampei (coffee
berry beetle), Ips spp. (engravers), Lasioderma serricorne
(cigarette beetle), Leptinotarsa decemlineata (Colorado potato
beetle), Liogenys fuscus, Liogenys suturalis, Lissorhoptrus
oryzophilus (rice water weevil), Lyctus spp. (wood beetles/powder
post beetles), Maecolaspis joliveti, Megascelis spp., Melanotus
communis, Meligethes spp., Meligethes aeneus (blossom beetle),
Melolontha melolontha (common European cockchafer), Oberea brevis,
Oberea linearis, Oryctes rhinoceros (date palm beetle),
Oryzaephilus mercator (merchant grain beetle), Oryzaephilus
surinamensis (sawtoothed grain beetle), Otiorhynchus spp.
(weevils), Oulema melanopus (cereal leaf beetle), Oulema oryzae,
Pantomorus spp. (weevils), Phyllophaga spp. (May/June beetle),
Phyllophaga cuyabana, Phyllotreta spp. (chrysomelids), Phynchites
spp., Popillia japonica (Japanese beetle), Prostephanus truncates
(larger grain borer), Rhizopertha dominica (lesser grain borer),
Rhizotrogus spp. (European chafer), Rhynchophorus spp. (weevils),
Scolytus spp. (wood beetles), Shenophorus spp. (billbug), Sitona
lineatus (pea leaf weevil), Sitophilus spp. (grain weevils),
Sitophilus granaries (granary weevil), Sitophilus oryzae (rice
weevil), Stegobium paniceum (drugstore beetle), Tribolium spp.
(flour beetles), Tribolium castaneum (red flour beetle), Tribolium
confusum (confused flour beetle), Trogoderma variabile (warehouse
beetle), and Zabrus tenebioides.
[0084] In another embodiment, the invention disclosed in this
document can be used to control Dermaptera (earwigs).
[0085] In another embodiment, the invention disclosed in this
document can be used to control Dictyoptera (cockroaches). A
non-exhaustive list of these pests includes, but is not limited to,
Blattella germanica (German cockroach), Blatta orientalis (oriental
cockroach), Parcoblatta pennylvanica, Periplaneta americana
(American cockroach), Periplaneta australoasiae (Australian
cockroach), Periplaneta brunnea (brown cockroach), Periplaneta
fuliginosa (smokybrown cockroach), Pyncoselus suninamensis (Surinam
cockroach), and Supella longipalpa (brownbanded cockroach).
[0086] In another embodiment, the invention disclosed in this
document can be used to control Diptera (true flies). A
non-exhaustive list of these pests includes, but is not limited to,
Aedes spp. (mosquitoes), Agromyza frontella (alfalfa blotch
leafminer), Agromyza spp. (leaf miner flies), Anastrepha spp.
(fruit flies), Anastrepha suspensa (Caribbean fruit fly), Anopheles
spp. (mosquitoes), Batrocera spp. (fruit flies), Bactrocera
cucurbitae (melon fly), Bactrocera dorsalis (oriental fruit fly),
Ceratitis spp. (fruit flies), Ceratitis capitata (Mediterranean
fruit fly), Chrysops spp. (deer flies), Cochliomyia spp.
(screwworms), Contarinia spp. (gall midges), Culex spp.
(mosquitoes), Dasineura spp. (gall midges), Dasineura brassicae
(cabbage gall midge), Delia spp., Delia platura (seedcorn maggot),
Drosophila spp. (vinegar flies), Fannia spp. (filth flies), Fannia
canicularis (little house fly), Fannia scalaris (latrine fly),
Gasterophilus intestinalis (horse bot fly), Gracillia perseae,
Haematobia irritans (horn fly), Hylemyia spp. (root maggots),
Hypoderma lineatum (common cattle grub), Liriomyza spp. (leafminer
flies), Liriomyza brassica (serpentine leafminer), Melophagus
ovinus (sheep ked), Musca spp. (muscid flies), Musca autumnalis
(face fly), Musca domestica (house fly), Oestrus ovis (sheep bot
fly), Oscinella frit (frit fly), Pegomyia betae (beet leafminer),
Phorbia spp., Psila rosae (carrot rust fly), Rhagoletis cerasi
(cherry fruit fly), Rhagoletis pomonella (apple maggot),
Sitodiplosis mosellana (orange wheat blossom midge), Stomoxys
calcitrans (stable fly), Tabanus spp. (horse flies), and Tipula
spp. (crane flies).
[0087] In another embodiment, the invention disclosed in this
document can be used to control Hemiptera (true bugs). A
non-exhaustive list of these pests includes, but is not limited to,
Acrosternum hilare (green stink bug), Blissus leucopterus (chinch
bug), Calocoris norvegicus (potato mirid), Cimex hemipterus
(tropical bed bug), Cimex lectularius (bed bug), Dagbertus
fasciatus, Dichelops furcatus, Dysdercus suturellus (cotton
stainer), Edessa meditabunda, Eurygaster maura (cereal bug),
Euschistus heros, Euschistus servus (brown stink bug), Helopeltis
antonii, Helopeltis theivora (tea blight plantbug), Lagynotomus
spp. (stink bugs), Leptocorisa oratorius, Leptocorisa varicornis,
Lygus spp. (plant bugs), Lygus hesperus (western tarnished plant
bug), Maconellicoccus hirsutus, Neurocolpus longirostris, Nezara
viridula (southern green stink bug), Phytocoris spp. (plant bugs),
Phytocoris californicus, Phytocoris relativus, Piezodorus
guildingi, Poecilocapsus lineatus (fourlined plant bug), Psallus
vaccinicola, Pseudacysta perseae, Scaptocoris castanea, and
Triatoma spp. (bloodsucking conenose bugs/kissing bugs).
[0088] In another embodiment, the invention disclosed in this
document can be used to control Homoptera (aphids, scales,
whiteflies, leafhoppers). A non-exhaustive list of these pests
includes, but is not limited to, Acrythosiphon pisum (pea aphid),
Adelges spp. (adelgids), Aleurodes proletella (cabbage whitefly),
Aleurodicus disperses, Aleurothrixus floccosus (woolly whitefly),
Aluacaspis spp., Amrasca bigutella bigutella, Aphrophora spp.
(leafhoppers), Aonidiella aurantii (California red scale), Aphis
spp. (aphids), Aphis gossypii (cotton aphid), Aphis pomi (apple
aphid), Aulacorthum solani (foxglove aphid), Bemisia spp.
(whiteflies), Bemisia argentifolii, Bemisia tabaci (sweetpotato
whitefly), Brachycolus noxius (Russian aphid), Brachycorynella
asparagi (asparagus aphid), Brevennia rehi, Brevicoryne brassicae
(cabbage aphid), Ceroplastes spp. (scales), Ceroplastes rubens (red
wax scale), Chionaspis spp. (scales), Chrysomphalus spp. (scales),
Coccus spp. (scales), Dysaphis plantaginea (rosy apple aphid),
Empoasca spp. (leafhoppers), Eriosoma lanigerum (woolly apple
aphid), Icerya purchasi (cottony cushion scale), Idioscopus
nitidulus (mango leafhopper), Laodelphax striatellus (smaller brown
planthopper), Lepidosaphes spp., Macrosiphum spp., Macrosiphum
euphorbiae (potato aphid), Macrosiphum granarium (English grain
aphid), Macrosiphum rosae (rose aphid), Macrosteles quadrilineatus
(aster leafhopper), Mahanarva frimbiolata, Metopolophium dirhodum
(rose grain aphid), Mictis longicornis, Myzus persicae (green peach
aphid), Nephotettix spp. (leafhoppers), Nephotettix cinctipes
(green leafhopper), Nilaparvata lugens (brown planthopper),
Parlatoria pergandii (chaff scale), Parlatoria ziziphi (ebony
scale), Peregrinus maidis (corn delphacid), Philaenus spp.
(spittlebugs), Phylloxera vitifoliae (grape phylloxera),
Physokermes piceae (spruce bud scale), Planococcus spp.
(mealybugs), Pseudococcus spp. (mealybugs), Pseudococcus brevipes
(pine apple mealybug), Quadraspidiotus perniciosus (San Jose
scale), Rhapalosiphum spp. (aphids), Rhapalosiphum maida (corn leaf
aphid), Rhapalosiphum padi (oat bird-cherry aphid), Saissetia spp.
(scales), Saissetia oleae (black scale), Schizaphis graminum
(greenbug), Sitobion avenae (English grain aphid), Sogatella
furcifera (white-backed planthopper), Therioaphis spp. (aphids),
Toumeyella spp. (scales), Toxoptera spp. (aphids), Trialeurodes
spp. (whiteflies), Trialeurodes vaporariorum (greenhouse whitefly),
Trialeurodes abutiloneus (bandedwing whitefly), Unaspis spp.
(scales), Unaspis yanonensis (arrowhead scale), and Zulia
entreriana.
[0089] In another embodiment, the invention disclosed in this
document can be used to control Hymenoptera (ants, wasps, and
bees). A non-exhaustive list of these pests includes, but is not
limited to, Acromyrrmex spp., Athalia rosae, Atta spp. (leafcutting
ants), Camponotus spp. (carpenter ants), Diprion spp. (sawflies),
Formica spp. (ants), Iridomyrmex humilis (Argentine ant),
Monomorium ssp., Monomorium minumum (little black ant), Monomorium
pharaonis (Pharaoh ant), Neodiprion spp. (sawflies), Pogonomyrmex
spp. (harvester ants), Polistes spp. (paper wasps), Solenopsis spp.
(fire ants), Tapoinoma sessile (odorous house ant), Tetranomorium
spp. (pavement ants), Vespula spp. (yellow jackets), and Xylocopa
spp. (carpenter bees).
[0090] In another embodiment, the invention disclosed in this
document can be used to control Isoptera (termites). A
non-exhaustive list of these pests includes, but is not limited to,
Coptotermes spp., Coptotermes curvignathus, Coptotermes frenchii,
Coptotermes formosanus (Formosan subterranean termite), Cornitermes
spp. (nasute termites), Cryptotermes spp. (drywood termites),
Heterotermes spp. (desert subterranean termites), Heterotermes
aureus, Kalotermes spp. (drywood termites), Incistitermes spp.
(drywood termites), Macrotermes spp. (fungus growing termites),
Marginitermes spp. (drywood termites), Microcerotermes spp.
(harvester termites), Microtermes obesi, Procornitermes spp.,
Reticulitermes spp. (subterranean termites), Reticulitermes
banyulensis, Reticulitermes grassei, Reticulitermes flavipes
(eastern subterranean termite), Reticulitermes hageni,
Reticulitermes hesperus (western subterranean termite),
Reticulitermes santonensis, Reticulitermes speratus, Reticulitermes
tibialis, Reticulitermes virginicus, Schedorhinotermes spp., and
Zootermopsis spp. (rotten-wood termites).
[0091] In another embodiment, the invention disclosed in this
document can be used to control Lepidoptera (moths and
butterflies). A non-exhaustive list of these pests includes, but is
not limited to, Achoea janata, Adoxophyes spp., Adoxophyes orana,
Agrotis spp. (cutworms), Agrotis ipsilon (black cutworm), Alabama
argillacea (cotton leafworm), Amorbia cuneana, Amyelosis
transitella (navel orangeworm), Anacamptodes defectaria, Anarsia
lineatella (peach twig borer), Anomis sabulifera (jute looper),
Anticarsia gemmatalis (velvetbean caterpillar), Archips argyrospila
(fruittree leafroller), Archips rosana (rose leaf roller),
Argyrotaenia spp. (tortricid moths), Argyrotaenia citrana (orange
tortrix), Autographa gamma, Bonagota cranaodes, Borbo cinnara (rice
leaf folder), Bucculatrix thurberiella (cotton leafperforator),
Caloptilia spp. (leaf miners), Capua reticulana, Carposina
niponensis (peach fruit moth), Chilo spp., Chlumetia transversa
(mango shoot borer), Choristoneura rosaceana (oblique banded
leafroller), Chrysodeixis spp., Cnaphalocerus medinalis (grass
leafroller), Colias spp., Conpomorpha cramerella, Cossus cossus
(carpenter moth), Crambus spp. (Sod webworms), Cydia funebrana
(plum fruit moth), Cydia molesta (oriental fruit moth), Cydia
nignicana (pea moth), Cydia pomonella (codling moth), Darna
diducta, Diaphania spp. (stem borers), Diatraea spp. (stalk
borers), Diatraea saccharalis (sugarcane borer), Diatraea
graniosella (southwester corn borer), Earias spp. (bollworms),
Earias insulata (Egyptian bollworm), Earias vitella (rough northern
bollworm), Ecdytopopha aurantianum, Elasmopalpus lignosellus
(lesser cornstalk borer), Epiphysias postruttana (light brown apple
moth), Ephestia spp. (flour moths), Ephestia cautella (almond
moth), Ephestia elutella (tobbaco moth), Ephestia kuehniella
(Mediterranean flour moth), Epimeces spp., Epinotia aporema,
Erionota thrax (banana skipper), Eupoecilia ambiguella (grape berry
moth), Euxoa auxiliaris (army cutworm), Feltia spp. (cutworms),
Gortyna spp. (stemborers), Grapholita molesta (oriental fruit
moth), Hedylepta indicata (bean leaf webber), Helicoverpa spp.
(noctuid moths), Helicoverpa armigera (cotton bollworm),
Helicoverpa zea (bollworm/corn earworm), Heliothis spp. (noctuid
moths), Heliothis virescens (tobacco budworm), Hellula undalis
(cabbage webworm), Indarbela spp. (root borers), Keiferia
lycopersicella (tomato pinworm), Leucinodes orbonalis (eggplant
fruit borer), Leucoptera malifoliella, Lithocollectis spp., Lobesia
botrana (grape fruit moth), Loxagrotis spp. (noctuid moths),
Loxagrotis albicosta (western bean cutworm), Lymantria dispar
(gypsy moth), Lyonetia clerkella (apple leaf miner), Mahasena
corbetti (oil palm bagworm), Malacosoma spp. (tent caterpillars),
Mamestra brassicae (cabbage armyworm), Maruca testulalis (bean pod
borer), Metisa plana (bagworm), Mythimna unipuncta (true armyworm),
Neoleucinodes elegantalis (small tomato borer), Nymphula
depunctalis (rice caseworm), Operophthera brumata (winter moth),
Ostrinia nubilalis (European corn borer), Oxydia vesulia, Pandemis
cerasana (common currant tortrix), Pandemis heparana (brown apple
tortrix), Papilio demodocus, Pectinophora gossypiella (pink
bollworm), Peridroma spp. (cutworms), Peridroma saucia (variegated
cutworm), Perileucoptera coffeella (white coffee leafminer),
Phthorimaea operculella (potato tuber moth), Phyllocnisitis
citrella, Phyllonorycter spp. (leafminers), Pieris rapae (imported
cabbageworm), Plathypena scabra, Plodia interpunctella (Indian meal
moth), Plutella xylostella (diamondback moth), Polychrosis viteana
(grape berry moth), Prays endocarpa, Prays oleae (olive moth),
Pseudaletia spp. (noctuid moths), Pseudaletia unipunctata
(armyworm), Pseudoplusia includens (soybean looper), Rachiplusia
nu, Scirpophaga incertulas, Sesamia spp. (stemborers), Sesamia
inferens (pink rice stem borer), Sesamia nonagrioides, Setora
nitens, Sitotroga cerealella (Angoumois grain moth), Sparganothis
pilleriana, Spodoptera spp. (armyworms), Spodoptera exigua (beet
armyworm), Spodoptera fugiperda (fall armyworm), Spodoptera
oridania (southern armyworm), Synanthedon spp. (root borers),
Thecla basilides, Thermisia gemmatalis, Tineola bisselliella
(webbing clothes moth), Trichoplusia ni (cabbage looper), Tuta
absoluta, Yponomeuta spp., Zeuzera coffeae (red branch borer), and
Zeuzera pyrina (leopard moth).
[0092] In another embodiment, the invention disclosed in this
document can be used to control Mallophaga (chewing lice). A
non-exhaustive list of these pests includes, but is not limited to,
Bovicola ovis (sheep biting louse), Menacanthus stramineus (chicken
body louse), and Menopon gallinea (common hen louse).
[0093] In another embodiment, the invention disclosed in this
document can be used to control Orthoptera (grasshoppers, locusts,
and crickets). A non-exhaustive list of these pests includes, but
is not limited to, Anabrus simplex (Mormon cricket), Gryllotalpidae
(mole crickets), Locusta migratoria, Melanoplus spp.
(grasshoppers), Microcentrum retinerve (angular winged katydid),
Pterophylla spp. (katydids), chistocerca gregaria, Scudderia
furcata (forktailed bush katydid), and Valanga nigricorni.
[0094] In another embodiment, the invention disclosed in this
document can be used to control Phthiraptera (sucking lice). A
non-exhaustive list of these pests includes, but is not limited to,
Haematopinus spp. (cattle and hog lice), Linognathus ovillus (sheep
louse), Pediculus humanus capitis (human body louse), Pediculus
humanus humanus (human body lice), and Pthirus pubis (crab
louse),
[0095] In another embodiment, the invention disclosed in this
document can be used to control Siphonaptera (fleas). A
non-exhaustive list of these pests includes, but is not limited to,
Ctenocephalides canis (dog flea), Ctenocephalides felis (cat flea),
and Pulex irritans (human flea).
[0096] In another embodiment, the invention disclosed in this
document can be used to control Thysanoptera (thrips). A
non-exhaustive list of these pests includes, but is not limited to,
Frankliniella fusca (tobacco thrips), Frankliniella occidentalis
(western flower thrips), Frankliniella shultzei Frankliniella
williamsi (corn thrips), Heliothrips haemorrhaidalis (greenhouse
thrips), Riphiphorothrips cruentatus, Scirtothrips spp.,
Scirtothrips citri (citrus thrips), Scirtothrips dorsalis (yellow
tea thrips), Taeniothrips rhopalantennalis, and Thrips spp.
[0097] In another embodiment, the invention disclosed in this
document can be used to control Thysanura (bristletails). A
non-exhaustive list of these pests includes, but is not limited to,
Lepisma spp. (silverfish) and Thermobia spp. (firebrats).
[0098] In another embodiment, the invention disclosed in this
document can be used to control Acarina (mites and ticks). A
non-exhaustive list of these pests includes, but is not limited to,
Acarapsis woodi (tracheal mite of honeybees), Acarus spp. (food
mites), Acarus siro (grain mite), Aceria mangiferae (mango bud
mite), Aculops spp., Aculops lycopersici (tomato russet mite),
Aculops pelekasi, Aculus pelekassi, Aculus schlechtendali (apple
rust mite), Amblyomma americanum (lone star tick), Boophilus spp.
(ticks), Brevipalpus obovatus (privet mite), Brevipalpus phoenicis
(red and black flat mite), Demodex spp. (mange mites), Dermacentor
spp. (hard ticks), Dermacentor variabilis (American dog tick),
Dermatophagoides pteronyssinus (house dust mite), Eotetranycus
spp., Eotetranychus carpini (yellow spider mite), Epitimerus spp.,
Eriophyes spp., Ixodes spp. (ticks), Metatetranycus spp., Notoedres
cati, Oligonychus spp., Oligonychus coffee, Oligonychus ilicus
(southern red mite), Panonychus spp., Panonychus citri (citrus red
mite), Panonychus ulmi (European red mite), Phyllocoptruta oleivora
(citrus rust mite), Polyphagotarsonemun latus (broad mite),
Rhipicephalus sanguineus (brown dog tick), Rhizoglyphus spp. (bulb
mites), Sarcoptes scabiei (itch mite), Tegolophus perseaflorae,
Tetranychus spp., Tetranychus urticae (two-spotted spider mite),
and Varroa destructor (honey bee mite).
[0099] In another embodiment, the invention disclosed in this
document can be used to control Nematoda (nematodes). A
non-exhaustive list of these pests includes, but is not limited to,
Aphelenchoides spp. (bud and leaf & pine wood nematodes),
Belonolaimus spp. (sting nematodes), Criconemella spp. (ring
nematodes), Dirofilaria immitis (dog heartworm), Ditylenchus spp.
(stem and bulb nematodes), Heterodera spp. (cyst nematodes),
Heterodera zeae (corn cyst nematode), Hirschmanniella spp. (root
nematodes), Hoplolaimus spp. (lance nematodes), Meloidogyne spp.
(root knot nematodes), Meloidogyne incognita (root knot nematode),
Onchocerca volvulus (hook-tail worm), Pratylenchus spp. (lesion
nematodes), Radopholus spp. (burrowing nematodes), and Rotylenchus
reniformis (kidney-shaped nematode).
[0100] In another embodiment, the invention disclosed in this
document can be used to control Symphyla (symphylans). A
non-exhaustive list of these pests includes, but is not limited to,
Scutigerella immaculata.
[0101] For more detailed information consult "Handbook of Pest
Control--The Behavior, Life History, and Control of Household
Pests" by Arnold Mallis, 9th Edition, copyright 2004 by GIE Media
Inc.
Mixtures
[0102] Some of the pesticides that can be employed beneficially in
combination with the invention disclosed in this document include,
but are not limited to the following,
[0103] 1,2-dichloropropane, 1,3-dichloropropene,
[0104] abamectin, acephate, acequinocyl, acetamiprid, acethion,
acetoprole, acrinathrin, acrylonitrile, alanycarb, aldicarb,
aldoxycarb, aldrin, allethrin, allosamidin, allyxycarb,
alpha-cypermethrin, alpha-ecdysone, amidithion, amidoflumet,
aminocarb, amiton, amitraz, anabasine, arsenous oxide, athidathion,
azadirachtin, azamethiphos, azinphos-ethyl, azinphos-methyl,
azobenzene, azocyclotin, azothoate,
[0105] barium hexafluorosilicate, barthrin, benclothiaz,
bendiocarb, benfuracarb, benomyl, benoxafos, bensultap,
benzoximate, benzyl benzoate, beta-cyfluthrin, beta-cypermethrin,
bifenazate, bifenthrin, binapacryl, bioallethrin, bioethanomethrin,
biopermethrin, bistrifluron, borax, boric acid, bromfenvinfos,
bromo-DDT, bromocyclen, bromophos, bromophos-ethyl, bromopropylate,
bufencarb, buprofezin, butacarb, butathiofos, butocarboxim,
butonate, butoxycarboxim,
[0106] cadusafos, calcium arsenate, calcium polysulfide,
camphechlor, carbanolate, carbaryl, carbofuran, carbon disulfide,
carbon tetrachloride, carbophenothion, carbosulfan, cartap,
chinomethionat, chlorantraniliprole, chlorbenside, chlorbicyclen,
chlordane, chlordecone, chlordimeform, chlorethoxyfos,
chlorfenapyr, chlorfenethol, chlorfenson, chlorfensulphide,
chlorfenvinphos, chlorfluazuron, chlormephos, chlorobenzilate,
chloroform, chloromebuform, chloromethiuron, chloropicrin,
chloropropylate, chlorphoxim, chlorprazophos, chlorpyrifos,
chlorpyrifos-methyl, chlorthiophos, chromafenozide, cinerin I,
cinerin II, cismethrin, cloethocarb, clofentezine, closantel,
clothianidin, copper acetoarsenite, copper arsenate, copper
naphthenate, copper oleate, coumaphos, coumithoate, crotamiton,
crotoxyphos, cruentaren A&B, crufomate, cryolite, cyanofenphos,
cyanophos, cyanthoate, cyclethrin, cycloprothrin, cyenopyrafen,
cyflumetofen, cyfluthrin, cyhalothrin, cyhexatin, cypermethrin,
cyphenothrin, cyromazine, cythioate,
[0107] d-limonene, dazomet, DBCP, DCIP, DDT, decarbofuran,
deltamethrin, demephion, demephion-O, demephion-S, demeton,
demeton-methyl, demeton-O, demeton-O-methyl, demeton-S,
demeton-S-methyl, demeton-S-methylsulphon, diafenthiuron, dialifos,
diamidafos, diazinon, dicapthon, dichlofenthion, dichlofluanid,
dichlorvos, dicofol, dicresyl, dicrotophos, dicyclanil, dieldrin,
dienochlor, diflovidazin, diflubenzuron, dilor, dimefluthrin,
dimefox, dimetan, dimethoate, dimethrin, dimethylvinphos,
dimetilan, dinex, dinobuton, dinocap, dinocap-4, dinocap-6,
dinocton, dinopenton, dinoprop, dinosam, dinosulfon, dinotefuran,
dinoterbon, diofenolan, dioxabenzofos, dioxacarb, dioxathion,
diphenyl sulfone, disulfiram, disulfoton, dithicrofos, DNOC,
dofenapyn, doramectin,
[0108] ecdysterone, emamectin, EMPC, empenthrin, endosulfan,
endothion, endrin, EPN, epofenonane, eprinomectin, esfenvalerate,
etaphos, ethiofencarb, ethion, ethiprole, ethoate-methyl,
ethoprophos, ethyl-DDD, ethyl formate, ethylene dibromide, ethylene
dichloride, ethylene oxide, etofenprox, etoxazole, etrimfos,
EXD,
[0109] famphur, fenamiphos, fenazaflor, fenazaquin, fenbutatin
oxide, fenchlorphos, fenethacarb, fenfluthrin, fenitrothion,
fenobucarb, fenothiocarb, fenoxacrim, fenoxycarb, fenpirithrin,
fenpropathrin, fenpyroximate, fenson, fensulfothion, fenthion,
fenthion-ethyl, fentrifanil, fenvalerate, fipronil, flonicamid,
fluacrypyrim, fluazuron, flubendiamide, flubenzimine, flucofuron,
flucycloxuron, flucythrinate, fluenetil, flufenerim, flufenoxuron,
flufenprox, flumethrin, fluorbenside, fluvalinate, fonofos,
formetanate, formothion, formparanate, fosmethilan, fospirate,
fosthiazate, fosthietan, furathiocarb, furethrin, furfural,
[0110] gamma-cyhalothrin, gamma-HCH,
[0111] halfenprox, halofenozide, HCH, HEOD, heptachlor,
heptenophos, heterophos, hexaflumuron, hexythiazox, HHDN,
hydramethylnon, hydrogen cyanide, hydroprene, hyquincarb,
[0112] imicyafos, imidacloprid, imiprothrin, indoxacarb,
iodomethane, IPSP, isamidofos, isazofos, isobenzan, isocarbophos,
isodrin, isofenphos, isoprocarb, isoprothiolane, isothioate,
isoxathion, ivermectin
[0113] jasmolin I, jasmolin II, jodfenphos, juvenile hormone I,
juvenile hormone II, juvenile hormone III,
[0114] kelevan, kinoprene,
[0115] lambda-cyhalothrin, lead arsenate, lepimectin, leptophos,
lindane, lirimfos, lufenuron, lythidathion,
[0116] malathion, malonoben, mazidox, mecarbam, mecarphon, menazon,
mephosfolan, mercurous chloride, mesulfen, mesulfenfos,
metaflumizone, metam, methacrifos, methamidophos, methidathion,
methiocarb, methocrotophos, methomyl, methoprene, methoxychlor,
methoxyfenozide, methyl bromide, methylchloroform, methylene
chloride, methyl isothiocyanate, metofluthrin, metolcarb,
metoxadiazone, mevinphos, mexacarbate, milbemectin, milbemycin
oxime, mipafox, mirex, MNAF, monocrotophos, morphothion,
moxidectin,
[0117] naftalofos, naled, naphthalene, nicotine, nifluridide,
nikkomycins, nitenpyram, nithiazine, nitrilacarb, novaluron,
noviflumuron,
[0118] omethoate, oxamyl, oxydemeton-methyl, oxydeprofos,
oxydisulfoton,
[0119] para-dichlorobenzene, parathion, parathion-methyl,
penfluron, pentachlorophenol, permethrin, phenkapton, phenothrin,
phenthoate, phorate, phosalone, phosfolan, phosmet, phosnichlor,
phosphamidon, phosphine, phosphocarb, phoxim, phoxim-methyl,
pirimetaphos, pirimicarb, pirimiphos-ethyl, pirimiphos-methyl,
potassium arsenite, potassium thiocyanate, pp'-DDT, prallethrin,
precocene I, precocene II, precocene III, primidophos, proclonol,
profenofos, profluthrin, promacyl, promecarb, propaphos,
propargite, propetamphos, propoxur, prothidathion, prothiofos,
prothoate, protrifenbute, pyraclofos, pyrafluprole, pyrazophos,
pyresmethrin, pyrethrin I, pyrethrin II, pyridaben, pyridalyl,
pyridaphenthion, pyrifluquinazon, pyrimidifen, pyrimitate,
pyriprole, pyriproxyfen,
[0120] quassia, quinalphos, quinalphos-methyl, quinothion,
quantiofos,
[0121] rafoxanide, resmethrin, rotenone, ryania,
[0122] sabadilla, schradan, selamectin, silafluofen, sodium
arsenite, sodium fluoride, sodium hexafluorosilicate, sodium
thiocyanate, sophamide, spinetoram, spinosad, spirodiclofen,
spiromesifen, spirotetramat, sulcofuron, sulfiram, sulfluramid,
sulfotep, sulfur, sulfuryl fluoride, sulprofos,
[0123] tau fluvalinate, tazimcarb, TDE, tebufenozide, tebufenpyrad,
tebupirimfos, teflubenzuron, tefluthrin, temephos, TEPP,
terallethrin, terbufos, tetrachloroethane, tetrachlorvinphos,
tetradifon, tetramethrin, tetranactin, tetrasul, theta
cypermethrin, thiacloprid, thiamethoxam, thicrofos, thiocarboxime,
thiocyclam, thiodicarb, thiofanox, thiometon, thionazin,
thioquinox, thiosultap, thuringiensin, tolfenpyrad, tralomethrin,
transfluthrin, transpermethrin, triarathene, triazamate,
triazophos, trichlorfon, trichlormetaphos-3, trichloronat,
trifenofos, triflumuron, trimethacarb, triprene,
[0124] vamidothion, vaniliprole,
[0125] XMC, xylylcarb,
[0126] zeta-cypermethrin and zolaprofos.
[0127] Additionally, any combination of the above pesticides can be
used.
[0128] The invention disclosed in this document can also be used
with herbicides and fungicides, or both for reasons of economy and
synergy.
[0129] The invention disclosed in this document can be used with
antimicrobials, bactericides, defoliants, safeners, synergists,
algaecides, attractants, desiccants, pheromones, repellants, animal
dips, avicides, disinfectants, semiochemicals, and molluscicides
(these categories not necessarily mutually exclusive) for reasons
of economy, and synergy.
[0130] For more information consult "Compendium of Pesticide Common
Names" located at http://www.alanwood.net/pesticides/index.html as
of the filing date of this document. Also consult "The Pesticide
Manual" 14th Edition, edited by C D S Tomlin, copyright 2006 by
British Crop Production Council.
Synergistic Mixtures
[0131] The invention disclosed in this document can be used with
other compounds such as the ones mentioned under the heading
"Mixtures" to form synergistic mixtures where the mode of action of
the compounds in the mixtures are the same, similar, or
different.
[0132] Examples of mode of actions include, but are not limited to:
acetylcholinesterase inhibitor; sodium channel modulator; chitin
biosynthesis inhibitor; GABA-gated chloride channel antagonist;
GABA- and glutamate-gated chloride channel agonist; acetylcholine
receptor agonist; MET I inhibitor; Mg-stimulated ATPase inhibitor;
nicotinic acetylcholine receptor; Midgut membrane disrupter; and
oxidative phosphorylation disrupter.
[0133] Additionally, the following compounds are known as
synergists and can be used with the invention disclosed in this
document: piperonyl butoxide, piprotal, propyl isome, sesamex,
sesamolin, and sulfoxide.
Formulations
[0134] A pesticide is rarely suitable for application in its pure
form. It is usually necessary to add other substances so that the
pesticide can be used at the required concentration and in an
appropriate form, permitting ease of application, handling,
transportation, storage, and maximum pesticide activity. Thus,
pesticides are formulated into, for example, baits, concentrated
emulsions, dusts, emulsifiable concentrates, fumigants, gels,
granules, microencapsulations, seed treatments, suspension
concentrates, suspoemulsions, tablets, water soluble liquids, water
dispersible granules or dry flowables, wettable powders, and ultra
low volume solutions.
[0135] For further information on formulation types see "Catalogue
of pesticide formulation types and international coding system"
Technical Monograph n.degree. 2, 5th Edition by CropLife
International (2002).
[0136] Pesticides are applied most often as aqueous suspensions or
emulsions prepared from concentrated formulations of such
pesticides. Such water-soluble, water-suspendable, or emulsifiable
formulations, are either solids, usually known as wettable powders,
or water dispersible granules, or liquids usually known as
emulsifiable concentrates, or aqueous suspensions. Wettable
powders, which may be compacted to form water dispersible granules,
comprise an intimate mixture of the pesticide, a carrier, and
surfactants. The concentration of the pesticide is usually from
about 10% to about 90% by weight. The carrier is usually chosen
from among the attapulgite clays, the montmorillonite clays, the
diatomaceous earths, or the purified silicates. Effective
surfactants, comprising from about 0.5% to about 10% of the
wettable powder, are found among sulfonated lignins, condensed
naphthalenesulfonates, naphthalenesulfonates,
alkylbenzenesulfonates, alkyl sulfates, and nonionic surfactants
such as ethylene oxide adducts of alkyl phenols.
[0137] Emulsifiable concentrates of pesticides comprise a
convenient concentration of a pesticide, such as from about 50 to
about 500 grams per liter of liquid dissolved in a carrier that is
either a water miscible solvent or a mixture of water-immiscible
organic solvent and emulsifiers. Useful organic solvents include
aromatics, especially xylenes and petroleum fractions, especially
the high-boiling naphthalenic and olefinic portions of petroleum
such as heavy aromatic naphtha. Other organic solvents may also be
used, such as the terpenic solvents including rosin derivatives,
aliphatic ketones such as cyclohexanone, and complex alcohols such
as 2-ethoxyethanol. Suitable emulsifiers for emulsifiable
concentrates are chosen from conventional anionic and nonionic
surfactants.
[0138] Aqueous suspensions comprise suspensions of water-insoluble
pesticides dispersed in an aqueous carrier at a concentration in
the range from about 5% to about 50% by weight. Suspensions are
prepared by finely grinding the pesticide and vigorously mixing it
into a carrier comprised of water and surfactants. Ingredients,
such as inorganic salts and synthetic or natural gums, may also be
added, to increase the density and viscosity of the aqueous
carrier. It is often most effective to grind and mix the pesticide
at the same time by preparing the aqueous mixture and homogenizing
it in an implement such as a sand mill, ball mill, or piston-type
homogenizer.
[0139] Pesticides may also be applied as granular compositions that
are particularly useful for applications to the soil. Granular
compositions usually contain from about 0.5% to about 10% by weight
of the pesticide, dispersed in a carrier that comprises clay or a
similar substance. Such compositions are usually prepared by
dissolving the pesticide in a suitable solvent and applying it to a
granular carrier which has been pre-formed to the appropriate
particle size, in the range of from about 0.5 to about 3 mm. Such
compositions may also be formulated by making a dough or paste of
the carrier and compound and crushing and drying to obtain the
desired granular particle size.
[0140] Dusts containing a pesticide are prepared by intimately
mixing the pesticide in powdered form with a suitable dusty
agricultural carrier, such as kaolin clay, ground volcanic rock,
and the like. Dusts can suitably contain from about 1% to about 10%
of the pesticide. They can be applied as a seed dressing or as a
foliage application with a dust blower machine.
[0141] It is equally practical to apply a pesticide in the form of
a solution in an appropriate organic solvent, usually petroleum
oil, such as the spray oils, which are widely used in agricultural
chemistry.
[0142] Pesticides can also be applied in the form of an aerosol
composition. In such compositions the pesticide is dissolved or
dispersed in a carrier, which is a pressure-generating propellant
mixture. The aerosol composition is packaged in a container from
which the mixture is dispensed through an atomizing valve.
[0143] Pesticide baits are formed when the pesticide is mixed with
food or an attractant or both. When the pests eat the bait they
also consume the pesticide. Baits may take the form of granules,
gels, flowable powders, liquids, or solids. They are used in pest
harborages.
[0144] Fumigants are pesticides that have a relatively high vapor
pressure and hence can exist as a gas in sufficient concentrations
to kill pests in soil or enclosed spaces. The toxicity of the
fumigant is proportional to its concentration and the exposure
time. They are characterized by a good capacity for diffusion and
act by penetrating the pest's respiratory system or being absorbed
through the pest's cuticle. Fumigants are applied to control stored
product pests under gas proof sheets, in gas sealed rooms or
buildings or in special chambers.
[0145] Pesticides can be microencapsulated by suspending the
pesticide particles or droplets in plastic polymers of various
types. By altering the chemistry of the polymer or by changing
factors in the processing, microcapsules can be formed of various
sizes, solubility, wall thicknesses, and degrees of penetrability.
These factors govern the speed with which the active ingredient
within is released, which in turn, affects the residual
performance, speed of action, and odor of the product.
[0146] Oil solution concentrates are made by dissolving pesticide
in a solvent that will hold the pesticide in solution. Oil
solutions of a pesticide usually provide faster knockdown and kill
of pests than other formulations due to the solvents themselves
having pesticidal action and the dissolution of the waxy covering
of the integument increasing the speed of uptake of the pesticide.
Other advantages of oil solutions include better storage stability,
better penetration of crevices, and better adhesion to greasy
surfaces.
[0147] Another embodiment is an oil-in-water emulsion, wherein the
emulsion comprises oily globules which are each provided with a
lamellar liquid crystal coating and are dispersed in an aqueous
phase, wherein each oily globule comprises at least one compound
which is agriculturally active, and is individually coated with a
monolamellar or oligolamellar layer comprising: (1) at least one
non-ionic lipophilic surface-active agent, (2) at least one
non-ionic hydrophilic surface-active agent and (3) at least one
ionic surface-active agent, wherein the globules having a mean
particle diameter of less than 800 nanometers. Further information
on the embodiment is disclosed in U.S. patent publication
20070027034 published Feb. 1, 2007, having patent application Ser.
No. 11/495,228. For ease of use this embodiment will be referred to
as "OIWE".
[0148] For further information consult "Insect Pest Management" 2nd
Edition by D. Dent, copyright CAB International (2000).
Additionally, for more detailed information consult "Handbook of
Pest Control--The Behavior, Life History, and Control of Household
Pests" by Arnold Mallis, 9th Edition, copyright 2004 by GIE Media
Inc.
Other Formulation Components
[0149] Generally, the invention disclosed in this document when
used in a formulation, such formulation can also contain other
components. These components include, but are not limited to, (this
is a non-exhaustive and non-mutually exclusive list) wetters,
spreaders, stickers, penetrants, buffers, sequestering agents,
drift reduction agents, compatibility agents, anti-foam agents,
cleaning agents, and emulsifiers. A few components are described
forthwith.
[0150] A wetting agent is a substance that when added to a liquid
increases the spreading or penetration power of the liquid by
reducing the interfacial tension between the liquid and the surface
on which it is spreading. Wetting agents are used for two main
functions in agrochemical formulations: during processing and
manufacture to increase the rate of wetting of powders in water to
make concentrates for soluble liquids or suspension concentrates;
and during mixing of a product with water in a spray tank to reduce
the wetting time of wettable powders and to improve the penetration
of water into water-dispersible granules. Examples of wetting
agents used in wettable powder, suspension concentrate, and
water-dispersible granule formulations are: sodium lauryl sulfate;
sodium dioctyl sulfosuccinate; alkyl phenol ethoxylates; and
aliphatic alcohol ethoxylates.
[0151] A dispersing agent is a substance which adsorbs onto the
surface of a particles and helps to preserve the state of
dispersion of the particles and prevents them from reaggregating.
Dispersing agents are added to agrochemical formulations to
facilitate dispersion and suspension during manufacture, and to
ensure the particles redisperse into water in a spray tank. They
are widely used in wettable powders, suspension concentrates and
water-dispersible granules. Surfactants that are used as dispersing
agents have the ability to adsorb strongly onto a particle surface
and provide a charged or steric barrier to reaggregation of
particles. The most commonly used surfactants are anionic,
non-ionic, or mixtures of the two types. For wettable powder
formulations, the most common dispersing agents are sodium
lignosulfonates. For suspension concentrates, very good adsorption
and stabilization are obtained using polyelectrolytes, such as
sodium naphthalene sulfonate formaldehyde condensates.
Tristyrylphenol ethoxylate phosphate esters are also used.
Nonionics such as alkylarylethylene oxide condensates and EO-PO
block copolymers are sometimes combined with anionics as dispersing
agents for suspension concentrates. In recent years, new types of
very high molecular weight polymeric surfactants have been
developed as dispersing agents. These have very long hydrophobic
`backbones` and a large number of ethylene oxide chains forming the
`teeth` of a `comb` surfactant. These high molecular weight
polymers can give very good long-term stability to suspension
concentrates because the hydrophobic backbones have many anchoring
points onto the particle surfaces. Examples of dispersing agents
used in agrochemical formulations are: sodium lignosulfonates;
sodium naphthalene sulfonate formaldehyde condensates;
tristyrylphenol ethoxylate phosphate esters; aliphatic alcohol
ethoxylates; alkyl ethoxylates; EO-PO block copolymers; and graft
copolymers.
[0152] An emulsifying agent is a substance which stabilizes a
suspension of droplets of one liquid phase in another liquid phase.
Without the emulsifying agent the two liquids would separate into
two immiscible liquid phases. The most commonly used emulsifier
blends contain alkylphenol or aliphatic alcohol with twelve or more
ethylene oxide units and the oil-soluble calcium salt of
dodecylbenzenesulfonic acid. A range of hydrophile-lipophile
balance ("HLB") values from 8 to 18 will normally provide good
stable emulsions. Emulsion stability can sometimes be improved by
the addition of a small amount of an EO-PO block copolymer
surfactant.
[0153] A solubilizing agent is a surfactant which will form
micelles in water at concentrations above the critical micelle
concentration. The micelles are then able to dissolve or solubilize
water-insoluble materials inside the hydrophobic part of the
micelle. The type of surfactants usually used for solubilization
are nonionics: sorbitan monooleates; sorbitan monooleate
ethoxylates; and methyl oleate esters.
[0154] Surfactants are sometimes used, either alone or with other
additives such as mineral or vegetable oils as adjuvants to
spray-tank mixes to improve the biological performance of the
pesticide on the target. The types of surfactants used for
bioenhancement depend generally on the nature and mode of action of
the pesticide. However, they are often nonionics such as: alkyl
ethoxylates; linear aliphatic alcohol ethoxylates; aliphatic amine
ethoxylates.
[0155] A carrier or diluent in an agricultural formulation is a
material added to the pesticide to give a product of the required
strength. Carriers arc usually materials with high absorptive
capacities, while diluents are usually materials with low
absorptive capacities. Carriers and diluents are used in the
formulation of dusts, wettable powders, granules and
water-dispersible granules.
[0156] Organic solvents are used mainly in the formulation of
emulsifiable concentrates, Ultra low volume formulations, and to a
lesser extent granular formulations. Sometimes mixtures of solvents
are used. The first main groups of solvents are aliphatic
paraffinic oils such as kerosene or refined paraffins. The second
main group and the most common comprises the aromatic solvents such
as xylene and higher molecular weight fractions of C9 and C10
aromatic solvents. Chlorinated hydrocarbons are useful as
cosolvents to prevent crystallization of pesticides when the
formulation is emulsified into water. Alcohols are sometimes used
as cosolvents to increase solvent power.
[0157] Thickeners or gelling agents are used mainly in the
formulation of suspension concentrates, emulsions and
suspoemulsions to modify the rheology or flow properties of the
liquid and to prevent separation and settling of the dispersed
particles or droplets. Thickening, gelling, and anti-settling
agents generally fall into two categories, namely water-insoluble
particulates and water-soluble polymers. It is possible to produce
suspension concentrate formulations using clays and silicas.
Examples of these types of materials, include, but are limited to,
montmorillonite, e.g. bentonite; magnesium aluminum silicate; and
attapulgite. Water-soluble polysaccharides have been used as
thickening-gelling agents for many years. The types of
polysaccharides most commonly used are natural extracts of seeds
and seaweeds or are synthetic derivatives of cellulose. Examples of
these types of materials include, but are not limited to, guar gum;
locust bean gum; carrageenam; alginates;
[0158] methyl cellulose; sodium carboxymethyl cellulose (SCMC);
hydroxyethyl cellulose (HEC). Other types of anti-settling agents
are based on modified starches, polyacrylates, polyvinyl alcohol
and polyethylene oxide. Another good anti-settling agent is xanthan
gum.
[0159] Microorganisms cause spoilage of formulated products.
Therefore preservation agents are used to eliminate or reduce their
effect. Examples of such agents include, but are not limited to:
propionic acid and its sodium salt; sorbic acid and its sodium or
potassium salts; benzoic acid and its sodium salt; p-hydroxybenzoic
acid sodium salt; methyl p-hydroxybenzoate; and
1,2-benzisothiazalin-3-one (BIT).
[0160] The presence of surfactants, which lower interfacial
tension, often causes water-based formulations to foam during
mixing operations in production and in application through a spray
tank. In order to reduce the tendency to foam, anti-foam agents are
often added either during the production stage or before filling
into bottles. Generally, there are two types of anti-foam agents,
namely silicones and non-silicones. Silicones are usually aqueous
emulsions of dimethyl polysiloxane while the non-silicone anti-foam
agents are water-insoluble oils, such as octanol and nonanol, or
silica. In both cases, the function of the anti-foam agent is to
displace the surfactant from the air-water interface.
[0161] For further information, see "Chemistry and Technology of
Agrochemical Formulations" edited by D. A. Knowles, copyright 1998
by Kluwer Academic Publishers. Also see "Insecticides in
Agriculture and Environment--Retrospects and Prospects" by A. S.
Perry, I. Yamamoto, I. Ishaaya, and R. Perry, copyright 1998 by
Springer-Verlag.
Applications
[0162] The actual amount of pesticide to be applied to loci of
pests is generally not critical and can readily be determined by
those skilled in the art. In general, concentrations from about
0.01 grams of pesticide per hectare to about 5000 grams of
pesticide per hectare are expected to provide good control.
[0163] The locus to which a pesticide is applied can be any locus
inhabited by an pest, for example, vegetable crops, fruit and nut
trees, grape vines, ornamental plants, domesticated animals, the
interior or exterior surfaces of buildings, and the soil around
buildings. Controlling pests generally means that pest populations,
activity, or both, are reduced in a locus. This can come about
when: pest populations are repulsed from a locus; when pests are
incapacitated, partially or completely, temporarily or permanently,
in or around a locus; or pests are exterminated, in whole or in
part, in or around a locus. Of course a combination of these
results can occur. Generally, pest populations, activity, or both
are desirably reduced more than fifty percent, preferably more than
90 percent, even more preferably 99 percent.
[0164] Generally, with baits, the baits are placed in the ground
where, for example, termites can come into contact with the bait.
Baits can also be applied to a surface of a building, (horizontal,
vertical, or slant surface) where, for example, ants, termites,
cockroaches, and flies, can come into contact with the bait.
[0165] Because of the unique ability of the eggs of some pests to
resist pesticides repeated applications may be desirable to control
newly emerged larvae.
[0166] Systemic movement of pesticides in plants may be utilized to
control pests on one portion of the plant by applying the
pesticides to a different portion of the plant, or to a location
where the root system of a plant can uptake pesticides. For
example, control of foliar-feeding insects can be controlled by
drip irrigation or furrow application, or by treating the seed
before planting. Seed treatment can be applied to all types of
seeds, including those from which plants genetically transformed to
express specialized traits will germinate. Representative examples
include those expressing proteins toxic to invertebrate pests, such
as Bacillus thuringiensis or other insecticidal toxins, those
expressing herbicide resistance, such as "Roundup Ready" seed, or
those with "stacked" foreign genes expressing insecticidal toxins,
herbicide resistance, nutrition-enhancement or any other beneficial
traits. Furthermore, such seed treatments with the invention
disclosed in this document can further enhance the ability of a
plant to better withstand stressful growing conditions. This
results in a healthier, more vigorous plant, which can lead to
higher yields at harvest time.
[0167] It should be readily apparent that the invention can be used
with plants genetically transformed to express specialized traits,
such as Bacillus thuringiensis or other insecticidal toxins, or
those expressing herbicide resistance, or those with "stacked"
foreign genes expressing insecticidal toxins, herbicide resistance,
nutrition-enhancement or any other beneficial traits. An example of
such a use is spraying such plants with the invention disclosed in
this document.
[0168] The invention disclosed in this document is suitable for
controlling endoparasites and ectoparasites in the veterinary
medicine sector or in the field of animal keeping. Compounds
according to the invention are applied here in a known manner, such
as by oral administration in the form of, for example, tablets,
capsules, drinks, granules, by dermal application in the form of,
for example, dipping, spraying, pouring on, spotting on, and
dusting, and by parenteral administration in the form of, for
example, an injection.
[0169] The invention disclosed in this document can also be
employed advantageously in livestock keeping, for example, cattle,
sheep, pigs, chickens, and geese. Suitable formulations are
administered orally to the animals with the drinking water or feed.
The dosages and formulations that are suitable depend on the
species.
[0170] Before a pesticide can be used or sold commercially, such
pesticide undergoes lengthy evaluation processes by various
governmental authorities (local, regional, state, national,
international). Voluminous data requirements are specified by
regulatory authorities and must be addressed through data
generation and submission by the product registrant or by another
on the product registrant's behalf. These governmental authorities
then review such data and if a determination of safety is
concluded, provide the potential user or seller with product
registration approval. Thereafter, in that locality where the
product registration is granted and supported, such user or seller
may use or sell such pesticide.
[0171] The headings in this document are for convenience only and
must not be used to interpret any portion thereof.
* * * * *
References