Note: Descriptions are shown in the official language in which they were submitted.
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TITLE
HERBICIDAL PYRAZOLES
BACKGROUND OF THE INVENTION
This invention relates to certain pyrazoles, their agriculturally suitable
salts and
compositions, and methods of their use for controlling undesirable vegetation.
The control of undesired vegetation is extremely important in achieving high
crop
efficiency. Achievement of selective control of the growth of weeds especially
in such
useful crops as rice, soybean, sugar beet, corn (maize), potato, wheat,
barley, tomato and
plantation crops, among others, is very desirable. Unchecked weed growth in
such useful
crops can cause significant reduction in productivity and thereby result in
increased costs to
the consumer. The control of undesired vegetation in noncrop areas is also
important. Many
products are commercially available for these purposes, but the need continues
for new
compounds which are more effective, less costly, less toxic, environmentally
safer or have
different modes of action.
SUMMARY OF THE INVENTION
This invention is directed to compounds of Formula I including all geometric
and
stereoisomers, agriculturally suitable salts thereof, agricultural
compositions containing them
and their use for controlling undesirable vegetation:
2
R4 RS
v
O SO
R3
I
wherein
A is -OC(=O)-, -OC(=O)O- or -OC(=O)S-, and the directionality of the A linkage
is
defined such that the moiety depicted on the left side of the linkage is
bonded to
the pyrazole ring and the moiety on the right side of the linkage is bonded to
Q;
Q is Ct-Ctp alkyl optionally substituted with halogen, C2-C~ alkoxyalkyl, C2-
Clo
alkenyl or C3-C6 cycloalkyl; or Q is phenyl, benzyl, pyridyl, furanyl or
thienyl,
each optionally substituted with C1-C3 alkyl, C~-C3 alkoxy, cyano, halogen,
COOH or S(=O)20H; or
A together with Q is -OC(=O)NR6R7;
R 1 is C t-C3 alkyl;
R2 and R3 are each independently H, C1-C3 alkyl or halogen;
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R4 and RS are taken together to form -O(CH2)20-; or R~ and R5 are taken
together
with the carbon to which they are attached to form C{=O);
R6 is C1-C3 alkyl, C3-C4 alkenyl or phenyl optionally substituted with 1-3 C1-
C3 alkyl,
C~-C3 alkoxy, halogen or cyano;
R~ is C1-C3 alkyl or C3-C4 alkenyl; or
R6 and R~ are taken together to form -CH2CH2CH2CH2-, -CH2CH2CH2CH2CH2- or
-CH2CH20CH2CH2-;
provided that when A is -OC(=O)- and R4 and RS are taken together to form
-O(CH2)20-, then Q is other than C1-C2 alkyl.
In the above recitations, the term "alkyl", used either alone or in compound
words such
as "alkylthio" or "haloalkyl" includes straight-chain or branched alkyl, such
as, methyl, ethyl,
n-propyl, i-propyl, or the different butyl, pentyl or hexyl isomers. The term
"1-2 alkyl"
indicates that one or two of the available positions for that substituent may
be alkyl which
are independently selected. "Alkenyl" includes straight-chain or branched
alkenes such as
ethenyl, 1-propenyl, 2-propenyl, and the different butenyl, pentenyl and
hexenyl isomers.
"Alkenyl" also includes polyenes such as 1,2-propadienyl and 2,4-hexadienyl.
"Alkynyl"
includes straight-chain or branched alkynes such as ethynyl, 1-propynyl, 2-
propynyl and the
different butynyl, pentynyl and hexynyl isomers. "Alkynyl" can also include
moieties
comprised of multiple triple bonds such as 2,5-hexadiynyl. "Alkoxy" includes,
for example,
methoxy, ethoxy, n-propyloxy, isopropyloxy and the different butoxy, pentoxy
and hexyloxy
isomers. "Cycloalkyl" includes, for example, cyclopropyl, cyclobutyl,
cyclopentyl, and
cyclohexyl.
The term "halogen", either alone or in compound words such as "haloalkyl",
includes
fluorine, chlorine, bromine or iodine. Further, when used in compound words
such as
"haloalkyl", said alkyl may be partially or fully substituted with halogen
atoms which may be
the same or different. Examples of "haloalkyl" include F3C, C1CH2, CF3CH2 and
CF3CC12.
The terms "haloalkenyl", "haloalkynyl", "haloalkoxy", "haloalkylthio", and the
like, are
defined analogously to the term "haloalkyl".
The total number of carbon atoms in a substituent group is indicated by the
"C;-C~"
prefix where i and j are numbers from 1 to 10. For example, C1-C3
alkylsulfonyl designates
methylsulfonyl through propylsulfonyl; C2 alkoxyalkyl designates CH30CH2; C3
alkoxyalkyl designates, for example, CH3CH(OCH3), CH30CH2CH2 or CH3CH20CH2;
and C4 alkoxyalkyl designates the various isomers of an alkyl group
substituted with an
alkoxy group containing a total of four carbon atoms, examples including
CH3CH2CH20CH2 and CH3CH~OCH2CH2. Examples of "alkylcarbonyl" include
C(O)CH3, C(O)CH2CH2CH3 and C(O)CH(CH3)2. Examples of "alkoxycarbonyl" include
CH30C(=O), CH3CH20C(=O), CH3CH2CH~OC(=O), (CH3)2CHOC(=O) and the different
butoxy- or pentoxycarbonyl isomers. In the above recitations, when a compound
of
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Formula I is comprised of one or more heterocyclic rings, all substituents are
attached to
these rings through any available carbon or nitrogen by replacement of a
hydrogen on said
carbon or nitrogen.
When a compound is substituted with a substituent bearing a subscript that
indicates
the number of said substituents can exceed 1, said substituents (when they
exceed 1 ) are
independently selected from the group of defined substituents. Further, when
the subscript
indicates a range, e.g. (R); ~, then the number of substituents may be
selected from the
integers between i and j inclusive.
When a group contains a substituent which can be hydrogen, for example R2 or
R3,
then, when this substituent is taken as hydrogen, it is recognized that this
is equivalent to said
group being unsubstituted.
Compounds of this invention can exist as one or more stereoisomers. The
various
stereoisomers include enantiomers, diastereomers, atropisomers and geometric
isomers. One
skilled in the art will appreciate that one stereoisomer may be more active
and/or may exhibit
beneficial effects when enriched relative to the other stereoisomer(s) or when
separated from
the other stereoisomer(s). Additionally, the skilled artisan knows how to
separate, enrich,
and/or to selectively prepare said stereoisomers. Accordingly, the present
invention
comprises compounds selected from Formula I and agriculturally suitable salts
thereof. The
compounds of the invention may be present as a mixture of stereoisomers,
individual
stereoisomers, or as an optically active form.
The salts of the compounds of the invention include acid-addition salts with
inorganic
or organic acids such as hydrobromic, hydrochloric, nitric, phosphoric,
sulfuric, acetic,
butyric, fumaric, lactic, malefic, malonic, oxalic, propionic, salicylic,
tartaric,
4-toluenesulfonic or valeric acids. The salts of the compounds of the
invention also include
those formed with organic bases (e.g., pyridine, ammonia, or triethylamine) or
inorganic
bases (e.g., hydrides, hydroxides, or carbonates of sodium, potassium,
lithium, calcium,
magnesium or barium) when the compound contains an acidic group such as a
carboxylic
acid or phenol.
Preferred compounds for reasons of better activity and/or ease of synthesis
are:
Preferred 1. Compounds of Formula I above, and agriculturally suitable salts
thereof,
wherein
R4 and RS are taken together to form -O(CH2)20-.
Preferred 2. Compounds of Preferred 1 wherein
Q is C~-C4 alkyl or C3-C6 cycloalkyl; or Q is phenyl optionally substituted
with C1-C3 alkyl, Ci-C3 alkoxy, cyano or halogen; and
R2 and R3 are each independently C~-C3 alkyl.
Preferred 3. Compounds of Preferred 2 wherein
A is -OC(=O)O-.
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Preferred 4. Compounds of Formula I above, and agriculturally suitable salts
thereof,
wherein
R4 and RS are taken together to form C(=O).
Preferred 5. Compounds of Preferred 4 wherein
Q is CI-C4 alkyl or C3-C6 cycloalkyl; or Q is phenyl optionally substituted
with C1-C3 alkyl, Cl-C3 alkoxy, cyano or halogen; and
R2 and R3 are each independently C1-C3 alkyl.
Preferred 6. Compounds of Preferred 5 wherein
A is -OC(=O)O-.
Most preferred are compounds of Formula I selected from the group:
(a) [4-[(2,3-dihydro-5,8-dimethylspiro[4H 1-benzothiopyran-4,2'-[1,3]dioxolan]-
6-
yl)carbonyl]-1-ethyl-1H-pyrazol-5-yl] (1-methylethyl) carbonate S,S dioxide;
(b) [4-[(3,4-dihydro-5,8-dimethyl-1,1-dioxido-4-oxo-2H 1-benzothiopyran-6-
yl)carbonyl]-1-ethyl-IH-pyrazol-5-yl] methyl carbonate;
(c) [4-[(3,4-dihydro-5,8-dimethyl-l,l-dioxido-4-oxo-2H I-benzothiopyran-6-
yl)carbonyl]-1-ethyl-1H pyrazol-S-yl] (I-methylethyl) carbonate;
(d) [4-[(2,3-dihydro-5,8-dimethylspiro[4H 1-benzothiopyran-4,2'-[1,3]dioxolan]-
6-
yl)carbonyl]-1-ethyl-IH pyrazol-5-yl] ethyl carbonate S,S-dioxide;
(e) [5-(benzoyloxy)-1-ethyl-1H pyrazol-4-yl](2,3-dihydro-5,8-dimethylspiro[4H
1-
benzothiopyran-4,2'-[1,3]dioxolan]-6-yl)methanone S,S-dioxide;
(f) [4-[(3,4-dihydro-1,1-dioxido-4-oxo-5,8-dimethyl-2H-benzothiopyran-6-
yl)carbonyl]-1-ethyl-IH pyrazol-5-yl] cyclopropanecarboxylate; and
(g) [4-[(2,3-dihydro-5,8-dimethylspiro[4~1 I-benzothiopyran-4,2'-
[1,3]dioxolan]-6-
yl)carbonyl]-1-ethyl-IH pyrazol-5-yl] cyclopropanecarboxylate S,S-dioxide.
This invention also relates to herbicidal compositions comprising herbicidally
effective
amounts of the compounds of the invention and at least one of a surfactant, a
solid diluent or
a liquid diluent. The preferred compositions of the present invention are
those which
comprise the above preferred compounds.
This invention also relates to a method for controlling undesired vegetation
comprising
applying to the locus of the vegetation herbicidally effective amounts of the
compounds of
the invention (e.g., as a composition described herein). The preferred methods
of use are
those involving the above preferred compounds.
DETAILS OF THE INVENTION
The compounds of Formula I can be prepared by one or more of the following
methods
and variations as described in Scheme 1. The definitions of Q and RI-R7 in the
compounds
of Formulae 1-5 below are as defined above in the Summary of the Invention.
Scheme 1 illustrates the preparation of compounds of Formula I whereby a
compound
of Formula 1 is reacted with the appropriate reagent of Formula 2, 3, 4, and 5
in the presence
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of a suitable base. This coupling method is carried out by general methods
known in the art;
see, for example, Nakamura, et al., WO 95/04054.
Scheme I
5
H O R2 R4 RS
i/ / ~ base and
I
N ~ \ QC(=O)Cl (2) or
Rl~ OH ~ S~ QOC(=O)Cl (3) or
R3 O O Q SC(=O)Cl (4) or
R~R7NC{=O)Cl (5)
Compounds of Formula 1 can be prepared by methods described in the art; see,
for
example, Tseng, WO 97/01550.
Compounds of Formulae 2, 3, 4, and 5 are either commercially available or can
be
prepared by methods well-established in the art from commercially available
starting
materials.
It is recognized that some reagents and reaction conditions described above
for
preparing compounds of Formula I may not be compatible with certain
functionalities
present in the intermediates. In these instances, the incorporation of
protection/deprotection
sequences or functional group interconversions into the synthesis will aid in
obtaining the
desired products. The use and choice of the protecting groups will be apparent
to one skilled
in chemical synthesis (see, for example, Greene, T. W.; Wuts, P. G. M.
Protective Groups in
Organic Synthesis, 2nd ed.; Wiley: New York, 1991 ). One skilled in the art
will recognize
that, in some cases, after the introduction of a given reagent as it is
depicted in any individual
scheme, it may be necessary to perform additional routine synthetic steps not
described in
detail to complete the synthesis of compounds of Formula I. One skilled in the
art will also
recognize that it may be necessary to perform a combination of the steps
illustrated in the
above schemes in an order other than that implied by the particular sequence
presented to
prepare the compounds of Formula I.
One skilled in the art will also recognize that compounds of Formula I and the
intermediates described herein can be subjected to various electrophilic,
nucleophilic,
radical, organometallic, oxidation, and reduction reactions to add
substituents or modify
existing substituents.
Without further elaboration, it is believed that one skilled in the art using
the preceding
description can utilize the present invention to its fullest extent. The
following Examples
are, therefore, to be construed as merely illustrative, and not limiting of
the disclosure in any
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way whatsoever. Percentages are by weight except for chromatographic solvent
mixtures or
where otherwise indicated. Parts and percentages for chromatographic solvent
mixtures are
by volume unless otherwise indicated. 1H NMR spectra are reported in ppm
downfield from
tetramethylsilane; s = singlet, d = doublet, t = triplet, q = quartet, m =
multiplet, dd = doublet
of doublets, dt = doublet of triplets, br s = broad singlet.
EXAMPLE 1
Step A: Preparation of 3-f(2,5-dimethylphen 1)~ thio)pro~anoic acid
43.4 g (1.086 mol) of sodium hydroxide was added to 230 mL of water, 75.0 g
(0.543
mol) of 2,5-dimethylthiophenol (purchased from Aldrich Chemical Company) was
then
I O added and the mixture was cooled to about 10 °C. 91.30 g (0.597
mol) of 3-bromopropionic
acid (purchased from Aldrich Chemical Company) was added in portions while
keeping the
temperature below 25 °C. The mixture was warmed to room temperature,
stirred for 2 h
under nitrogen, and was then washed with diethyl ether (3 x 500 mL). The
aqueous layer
was acidified with 1N HCl and filtered to yield 112.79 g of the title compound
of Step A as a
solid melting at 97-98 °C. 1H NMR {CDCl3): 8 2.3 (s,3H), 2.34 (s,3H),
2.68 (t,2H), 3.1
(t,2H), 6.9 (d, l H), 7.06-7.14 (2H).
Step B: Preparation of 2,3-dihydro-5,8-dimethyl-4H 1-benzopyran-4-one
530 mL of concentrated sulfuric acid was added to 24.91 g (0.119 mol) of the
title
compound of Step A while being cooled with an acetone/ice bath. The ice bath
was
removed, the mixture was stirred for 1 h and was then poured over crushed ice.
The aqueous
mixture was extracted with a 1 : 9 mixture of diethyl ether : hexane (6 x 500
mL), dried
(MgS04), filtered, and evaporated to dryness to yield 11.75 g of the title
compound of Step B
as an oil. 1H NMR (CDC13): 8 2.3 (s,3H), 2.6 (s,3H), 2.97 (m,2H), 3.2 (m,2H),
6.9-7.1
(2H).
Step C: Preparation of 6-bromo-2,3-dihydro-5,8-dimethyl-4H 1-benzothiopyran-4-
one
A solution of 4.07 g (0.021 mol) of the title compound of Step B in 25 mL of
methylene chloride was added dropwise to a mixture of 7.07 g (0.053 mol) of
aluminum
chloride (purchased from Aldrich Chemical Company) and 25 mL of methylene
chloride.
The suspension was stirred for approximately 15 minutes, 1.14 mL (0.022 mol)
of bromine
(purchased from Janssen) was added dropwise, and the mixture was refluxed for
I 0 minutes.
The warm mixture was poured into 10 mL of concentrated hydrochloric acid
containing 75 g
of ice, stirred for 10 minutes, diluted with 50 mL of water, and then
extracted with diethyl
ether (2 x 200 mL). The combined organic layers were washed with water (2 x
200 mL),
dried (Na2S04), filtered, and evaporated to dryness. The crude product was
chromatographed over silica gel eluting with a mixture of ethyl acetate :
hexane (5% : 95%)
to yield 2.62 g of the title compound of Step C as a solid melting at 87-88
°C. 1H NMR
(CDC13): b 2.3 (s,3H), 2.6 (s,3H), 3.0 (m,2H), 3.2 (m,2H), 7.45 (s,lH).
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Step D: Preparation of 6-bromo-2,3-dihydro-5 8-dimethylspiro(4~1 1-
benzothionvran-
4 2'-( 1,3ldioxolanel
26.06 g (0.096 mol) of the title compound of Step C, 250 mL of ethylene
glycol, 170
mL of trimethyl orthoformate (purchased from Aldrich Chemical Company), and
0.06 g of
p-toluenesulfonic acid monohydrate were stirred together at 80 °C under
nitrogen overnight.
The mixture was diluted with 400 mL of diethyl ether. The resulting mixture
was washed
with a 1:1 mixture of 1N sodium hydroxide: saturated aqueous NaCI (2 x 600 mL)
and then
with saturated aqueous NaCI ( 1 x 600 mL). The organic layer was dried
{Na2S04), filtered,
and evaporated to dryness. The crude product was chromatographed over silica
gel eluting
with a mixture of ethyl acetate : hexane ( 1 : 9) to yield 24.73 g of the
title compound of
Step D as a solid melting at 97 °C (dec). tH NMR (CDC13): 8 2.2 (s,3H),
2.3 (m,2H), 2.4
(s,3H), 3.0 (m,2H), 4.15 (m,2H), 4.3 (m,2H), 7.3 (s,lH).
Step E: Preparation of 2 3-dihydro-5 8-dimethylspiro~j4H I-benzothiopyran 4 2'
j 1,3ldioxolane]-6-carboxylic acid
24.73 g (0.078 mol) of the title compound of Step D was added to 150 mL of
tetrahydrofuran. The solution was cooled to about -70 ° under nitrogen
and 37.68 mL (0.094
mol) of 2.5M n-butyllithium in hexane was added dropwise while keeping the
temperature
below -65 °C. After stirnng for 1 h, carbon dioxide was bubbled into
the mixture for 2 h.
The mixture was allowed to warm to room temperature, 300 mL of hexanes were
added, and
the resulting mixture was filtered. The resulting solid was added to a mixture
of water
methylene chloride (400 mL : 400 mL), cooled to about 0 °C, and
acidified to pH 1 with
concentrated hydrochloric acid. The layers were separated and the aqueous
layer was
extracted with diethyl ether (2 x 300 mL). The combined organic layers were
dried
(MgS04), filtered, and evaporated to dryness to yield 4.73 g of the title
compound of Step E
as a solid melting at 207-208 °C. 1H NMR (Me2S0-d6): 8 2.2 (m,SH), 2.4
(s,3H), 3.0
(m,2H), 4. I -4.2 (m,4H), 7.4 (s, l H).
Step F: Preparation of 2,3-dihydro-5 8-dimeth ~~lspiroj4H 1-ben~othio~yran-4
2'-
(1,31dioxolanel-6-carboxylic acid 1 I-dioxide
4.73 g (0.017 mol) of the title compound of Step E and 2.08 g (0.025 mol) of
sodium
acetate were added to 85 mL of methanol. The solution was cooled to about 0
°C, and a
solution of 17.66 g (0.029 mol) of OXONE~ (purchased from Aldrich Chemical
Company)
in 85 mL of water was added dropwise while keeping the temperature below 6
°C. The
mixture was warmed to room temperature and stirred under nitrogen overnight.
The mixture
was diluted with 50 mL of water, cooled to about 0 °C, acidified to
around pH 2 with
concentrated hydrochloric acid, and then extracted with chloroform {3 x 150
mL). The
combined organic layers were dried (MgS04), filtered, and evaporated to
dryness. The
residue was triturated in diethyl ether : hexane (1 : 9) which was decanted to
yield 4.18 g of
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the title compound of Step F as a solid melting at 185 °C (dec). 1H NMR
(Me2S0-d6): S
2.35 (s,3H), 2.5 (m,2H), 2.6 (s,3H), 3.5 (m,2H), 4.16 (m,2H), 4.2 (m,2H), 7.6
(s,lH}.
Step G: Preparation of 1-ethyl-1~1 pyrazol-5-yl 2,3-dihydro-5,8-
dimethylspirof4H 1
benzothiopyran-4,2'-f 1,31dioxolane)-6-carboxylate 1,1-dioxide
1.18 g (3.8 mmol) of the title compound of Step F, 0.99 mL (0.011 mol) of
oxalyl
chloride (purchased from Janssen), and 2 drops of N,N dimethylformamide were
added to 50
mL of methylene chloride. The mixture was refluxed under nitrogen for 2 h, and
was then
evaporated to dryness. 50 mL of methylene chloride was added to the residue
and the
resulting mixture was evaporated to dryness. Another SO mL of methylene
chloride was
added to the residue, and the solution was cooled to about 0 °C. 0.51 g
(4.5 mmol) of 1-
ethyl-1~1-pyrazol-5-0l was added followed by 1.63 mL (0.012 mol) of
triethylamine, and the
mixture was stirred overnight while warming to room temperature. The mixture
was
evaporated to dryness and the crude product was chromatographed eluting with a
mixture of
ethyl acetate : hexane (6 : 4) to yield 0.24 g of the title compound of Step G
as a semi-solid.
1H NMR (CDCl3): 8 1.4 (t,3H), 2.5 (s,3H), 2.6 (m,2H), 2.8 (s,3H), 3.5 (m,2H),
4.1-4.4
(m,6H), 6.26 (s,lH), 7.5-7.7 (2H).
Step H: Preparation of (2,3-dih~dro-5,8-dimethylspirof4H 1-benzothiopyran-4,2'-
j1,31dioxolanl-6-yl)(I-ethyl-5-hydrox -y l~l-nyrazol-4-yl)methanone S,S-
dioxide
0.24 g (0.59 mmol) of the title compound of Step G, 0.25 drops of acetone
cyanohydrin (purchased from Aldrich Chemical Company), and 0.14 mL ( I .0
mmol) of
triethylamine were added to 25 mL of acetonitrile and the mixture was allowed
to stir at
room temperature under nitrogen for 1.5 h. About 0.06 g of potassium cyanide
was added to
the mixture which then was stirred at room temperature overnight. The mixture
was
evaporated to dryness and water was added to the residue. The resulting
mixture was
acidified to pH 1 with concentrated hydrochloric acid and extracted with
methylene chloride
(2 x 50 mL). The combined organic layers were dried (MgS04), filtered, and
evaporated to
dryness to yield 0.17 g of the title compound of Step H as a solid melting at
111 °C (dec).
1H NMR (CDC13): 8 1.46 (t,3H), 2.3 (s,3H), 2.6 (m,2H), 2.8 (s,3H), 3.5 (m,2H),
4.1 (q,2H),
4.2-4.3 (m,4H), 7.3 (2H).
Step I: Preparation of f4-[(2,3-dihydro-5,8-dimethylspiro(4H 1-
benzothio~yran,4,2'-
(1,31dioxolanl-6-yl)carbonyl]'~-1-ethyl-IH pyrazol-5-yll (I-methylethyl)
carbonate S,S-dioxide
500 mg (1.23 mmol) of the title compound of Step H and 1.50 ml (1.50 mmol) of
isopropylchloroformate (1.0 M solution in toluene; purchased from Aldrich
Chemical Co.)
were added to acetonitrile, followed by the addition of 0.220 ml (1.56 mmol)
of
triethylamine. The solution was stirred under nitrogen at room temperature
overnight. The
mixture was evaporated to dryness and chromatographed over silica gel, eluting
with a
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9
mixture of 33% hexanes in ethyl acetate to yield 440 mg of the title compound
of Step I, a
compound of this invention, as a yellow solid melting at 168-170 °C. ~H
NMR (CDC13): S
I .4 (m, 9H), 2.3 (s, 3H), 2.6 (m, 2H), 2.8 (s, 3H), 3.5 (m, 2H), 4.1 (m, 4H),
4.3 (m, 2H), 5.0
(q, 1H), 7.2 (s, IH), 7.5 (s, IH).
EXAMPLE 2
Step A: Preparation of f4-f(2,3-dihydro-5 8-dimethylspirof4H I-ben~othiopyran
4 2'-
f 1,31dioxolanl-6-yl)carbonyl}-I-ethyl-lHwrazol-5-yll ethyl carbonate SS-
dioxide
400 mg ( 1.00 mmol) of the title compound of Step H in Example 1 was added to
acetonitrile and cooled to -78 °C. To the cooled solution was added
0.115 ml (1.20 mmol) of
ethyl chloroformate (purchased from Aldrich Chemical Co.), followed by the
addition of
0.175 ml (1.26 mmol) of triethylamine. The solution was allowed to warm to
ambient
temperature and stirred under nitrogen overnight. The mixture was concentrated
to dryness
under reduced pressure and chromatog~raphed over silica gel, eluting with a
mixture of 50%
hexanes in ethyl acetate. The title compound of Step A, a compound of this
invention, was
isolated as a solid with a melting point of 201-203 °C. ~H NMR (CDC13):
8 1.43 (m, 6H),
2.28 (s, 3H), 2.60 (m, 2H), 2.76 (s, 3H), 3.55 (m, 2H), 4.0- 4.4 (m, 8H), 7.20
(s, 1H}, 7.56
(s, IH).
By the procedures described herein together with methods known in the art, the
following compounds of Tables 1 to 4 can be prepared.
Table I
R
R1 R2 R3 A Q
CH3 H H -OC(=O)O- CH3
CH3 CH3 H -OC{=O)O- CH3
CH3 CH3 CH3 -OC(=O)O- CH3
CH3 CH3 CI -OC(=O)O- CH3
CH3 Cl CH3 -OC(=O)O- CH3
CH3 Cl Cl -OC(=O)O- CH3
CH3 H H -OC(=O)S- CH3
Q
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CH3 CH3 H -OC(=O)S- CH3
CH3 CH3 CH3 -OC(=O)S- CH3
CH3 CH3 Cl -OC(=O)S- CH3
CH3 Cl CH3 -OC(=O)S- CH3
CH3 Cl Cl -OC{=O)S- CH3
CH2CH3 H H -OC(=O)O- CH3
CH2CH3 CH3 H -OC(=O)O- CH3
CH2CH3 CH3 CH3 -OC(=O)O- CH3
CH2CH3 CH3 Cl -OC(=O)O- CH3
CH2CH3 Cl CH3 -OC(=O)O- CH3
CH2CH3 Cl Cl -OC(=O)O- CH3
CH2CH3 H H -OC(=O)S- CH3
CH2CH3 CH3 H -OC(=O)S- CHI
CH2CH3 CH3 CH3 -OC(=O)S- CH3
CH2CH3 CH3 Cl -OC(=O)S- CH3
CH2CH3 Cl CH3 -OC(=O}S- CH3
CH2CH3 Cl CI -OC(=O)S- CH3
CH2CH~CH3 H H -OC(=O)O- CH3
CH~CH2CH3 CH3 H -OC(=O)O- CH3
CH2CH2CH3 CH3 CH3 -OC(=O)O- CH3
CH2CH2CH3 CH3 Cl -OC(=O)O- CH3
CH2CH2CH3 Cl CH3 -OC{=O)O- CH3
CH2CH2CH3 Cl Cl -OC(=O}O- CH3
CHZCH2CH3 H H -OC{=O)S- CH3
CH2CH2CH3 CH3 H -OC(=O)S- CH3
CH2CH2CH3 CH3 CH3 -OC(=O)S- CH3
CH~CH~CH3 CH3 Cl -OC(=O)S- CH3
CH2CH2CH3 Cl CH3 -OC(=O)S- CH3
CH2CH~CH3 C1 Cl -OC(=O)S- CH3
CH3 H H -OC(=O)O- CH~CH3
CH3 CH3 H -OC(=O)O- CH2CH3
CH3 CH3 CH3 -OC(=O)O- CH2CH3
CH3 CH3 Cl -OC{=O)O- CH2CH3
CH3 C1 CH3 -OC(=O)O- CH2CH3
CH3 Cl Cl -OC(=O)O- CH2CH3
CH3 H H -OC(=O)S- CH2CH3
CH3 CH3 H -OC(=O)S- CH2CH3
CH3 CH3 CH3 -OC(=O)S- CH2CH3
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CH3 CH3 CI -OC(=O)S- CH2CH3
CH3 CI CH3 -OC{=O)S- CH2CH3
CH3 Cl Cl -OC(=O)S- CH2CH3
CH2CH3 H H -OC(=O)O- CH2CH3
CH2CH3 CH3 H -OC(=O)O- CH2CH3
CH2CH3 CH3 CH3 -OC(=O)O- CH2CH3
CH2CH3 CH3 Cl -OC(=O)O- CH2CH3
CH2CH3 Cl CH3 -OC(=O)O- CH2CH3
CH2CH3 Cl CI -OC(=O)O- CH2CH3
CH2CH3 H H -OC(=O)S- CH~CH3
CH2CH3 CH3 H -OC(=O)S- CH2CH3
CH2CH3 CH3 CH3 -OC(=O)S- CH2CH3
CH2CH3 CH3 Cl -OC(=O)S- CH2CH3
CH2CH3 C1 CH3 -OC(=O)S- CH2CH3
CH2CH3 CI CI -OC(=O)S- CH2CH3
CH2CH2CH3 H H -OC(=O)O- CH2CH3
CH2CH2CH3 CH3 H -OC(=O)O- CH2CH3
CH2CH~CH3 CH3 CH3 -OC(=O)O- CH2CH3
CH2CH2CH3 CH3 CI -OC(=O)O- CH2CH3
CH2CH2CH3 CI CH3 -OC(=O)O- CH2CH3
CH2CH2CH3 Cl CI -OC(=O)O- CH2CH3
CH2CH2CH3 H H -OC(=O)S- CH2CH3
CH2CH2CH3 CH3 H -OC(=O)S- CH2CH3
CH2CH2CH3 CH3 CH3 -OC(=O)S- CH~CH3
CH2CH2CH3 CH3 C1 -OC(=O)S- CH~CH3
CHzCH2CH3 CI CH3 -OC(=O)S- CH2CH3
CH2CH2CH3 Cl CI -OC(=O)S- CH2CH3
CH3 H H -OC(=O)O- CH2CH2CH3
CH3 CH3 H -OC(=O)O- CH2CH2CH3
CH3 CH3 CH3 -OC(=O)O- CH2CH2CH3
CH3 CH3 CI -OC(=O)O- CH2CH2CH3
CH3 CI CH3 -OC(=O)O- CH2CH2CH3
CH3 Cl Cl -OC(=O)O- CH2CH~CH3
CH3 H H -OC(=O)S- CH2CH2CH3
CH3 CH3 H -OC(=O)S- CH2CH2CH3
CH3 CH3 CH3 -OC(=O)S- CH2CH~CH3
CH3 CH3 Ci -OC(=O)S- CH2CH2CH3
CH3 Cl CH3 -OC(=O)S- CH2CH2CH3
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CH3 C1 C1 -OC(=O)S- CH2CH2CH3
CH2CH3 H H -OC(=O)O- CH2CH2CH3
CH2CH3 CH3 H -OC(=O)O- CH2CH2CH3
CH2CH3 CH3 CH3 -OC(=O)O- CH2CH2CH3
CH2CH3 CH3 C1 -OC(=O)O- CH2CH2CH3
CH2CH3 Cl CH3 -OC(=O)O- CH2CH2CH3
CHZCH3 Cl Cl -OC(=O)O- CH2CH2CH3
CH2CH3 H H -OC(=O)S- CH2CH2CH3
CH2CH3 CH3 H -OC(=O)S- CH2CH2CH3
CH2CH3 CH3 CH3 -OC(=O)S- CH2CH2CH3
CH2CH3 CH3 Cl -OC(=O)S- CH2CH2CH3
CH2CH3 Cl CH3 -OC(=O)S- CH2CH2CH3
CH2CH3 C1 Cl -OC(=O)S- CH2CH2CH3
CH2CH2CH3 H H -OC(=O)O- CH2CH2CH3
CH2CH2CH3 CH3 H -OC(=O)O- CH2CH2CH3
CH2CH2CH3 CH3 CH3 -OC(=O)O- CH2CH~CH3
CH2CH2CH3 CH3 Cl -OC(=O)O- CH~CHZCH3
CH2CH2CH3 Cl CH3 -OC(=O)O- CH~CH~CH3
CH2CH2CH3 CI Cl -OC(=O)O- CH~CH~CH3
CH2CH2CH3 H H -OC(=O)S- CH2CH2CH3
CHZCH2CH3 CH3 H -OC(=O)S- CH~CH2CH3
CH2CHZCH3 CH3 CH3 -OC(=O)S- CH2CH2CH3
CH~CH2CH3 CH3 C1 -OC(=O)S- CH2CH2CH3
CH2CH2CH3 Cl CH3 -OC(=O)S- CH2CH2CH3
CH2CH2CH3 Cl Cl -OC(=O)S- CH2CH2CH3
CH3 H H -OC(=O)O- cyclo-propyl
CH3 CH3 H -OC(=O)O- cyclo-propyl
CH3 CH3 CH3 -OC(=O}O- cyclo-propyl
CH3 CH3 Cl -OC(=O)O- cvclo-propyl
CH3 Cl CH3 -OC(=O)O- cyclo-propyl
CH3 Cl Cl -OC(=O)O- cyclo-propyl
CH3 H H -OC(=O)S- cyclo-propyl
CH3 CH3 H -OC(=O)S- cyclo-propyl
CH3 CH3 CH3 -OC(=O)S- cyclo-propyl
CH3 CH3 Cl -OC(=O)S- cyclo-propyl
CH3 CI CH3 -OC(=O)S- cyclo-propyl
CH3 Cl Cl -OC(=O)S- cvclo-propyl
CH2CH3 H H -OC(=O)O- cyclo-propyl
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CH2CH3 CH3 H -OC(=O)O- cyclo-propyl
CH2CH3 CH3 CH3 -OC(=O)O- cyclo-propyl
CH2CH3 CH3 CI -OC(=O)O- cyclo-propyl
CH~CH3 CI CH3 -OC(=O)O- cyclo-propyl
CH2CH3 Cl Cl -OC(=O)O- cyclo-propyl
CH2CH3 H H -OC(=O)S- cyclo-propyl
CHZCH3 CH3 H -OC(=O)S- cyclo-propyl
CH2CH3 CH3 CH3 -OC(=O)S- cyclo-propyl
CH2CH3 CH3 Cl -OC(=O)S- cyclo-propyl
CH2CH3 Cl CH3 -OC(=O)S- cyclo-propyl
CH2CH3 Cl Cl -OC(=O)S- cyclo-propyl
CH2CH2CH3 H H -OC(=O)O- cyclo-propyl
CH~CH2CH3 CH3 H -OC(=O)O- cyclo-propyl
CH2CH2CH3 CH3 CH3 -OC(=O)O- cyclo-propyl
CH2CH2CH3 CH3 CI -OC(=O)O- cyclo-propyl
CH2CH2CH3 CI CH3 -OC(=O)O- cyclo-propyl
CH2CH2CH3 Cl Cl -OC(=O)O- cyclo-propyl
CH~CH2CH3 H H -OC(=O)S- cyclo-propyl
CH2CH2CH3 CH3 H -OC(=O)S- cyclo-propyl
CH2CH2CH3 CH3 CH3 -OC(=O)S- cyclo-propyl
CH2CH~CH3 CH3 Cl -OC(=O)S- cyclo-propyl
CH2CH2CH3 Cl CH3 -OC(=O)S- cyclo-propyl
CH2CH2CH3 Cl Cl -OC(=O)S- cyclo-propyl
CH3 H H -OC(=O)O- CH=CH2
CH3 CH3 H -OC(=O)O- CH=CH2
CH3 CH3 CH3 -OC(=O)O- CH=CH2
CH3 CH3 Cl -OC(=O)O- CH=CHI
CH3 Cl CH3 -OC(=O)O- CH=CH2
CH3 Cl Cl -OC(=O)O- CH=CH2
CH3 H H -OC(=O)S- CH=CH2
CH3 CH3 H -OC(=O)S- CH=CH2
CH3 CH3 CH3 -OC(=O)S- CH=CH2
CH3 CH3 Cl -OC(=O)S- CH=CH2
CH3 CI CH3 -OC(=O)S- CH=CH2
CH3 Cl C1 -OC(=O)S- CH=CH2
CH2CH3 H H -OC(=O)O- CH=CH2
CH2CH3 CH3 H -OC(=O)O- CH=CH2
CH2CH3 CH3 CH3 -OC(=O)O- CH=CHZ
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CH2CH3 CH3 CI -OC(=O)O- CH=CH2
CH2CH3 CI CH3 -OC(=O)O- CH=CH2
CH2CH3 Cl Cl -OC(=O)O- CH=CH2
CH2CH3 H H -OC(=O)S- CH=CH2
CH2CH3 CH3 H -OC(=O)S- CH=CH2
CH2CH3 CH3 CH3 -OC(=O)S- CH=CH2
CH2CH3 CH3 CI -OC(=O)S- CH=CH2
CH2CH3 CI CH3 -OC{=O)S- CH=CH2
CHzCH3 CI CI -OC{=O)S- CH=CH2
CHZCH2CH3 H H -OC(=O)O- CH=CH2
CH2CH2CH3 CH3 H -OC(=O)O- CH=CH2
CH2CH2CH3 CH3 CH3 -OC(=O)O- CH=CH2
CH2CH2CH3 CH3 CI -OC(=O)O- CH=CH2
CH2CH2CH3 CI CH3 -OC(=O)O- CI-I=CHI
CH2CH2CH3 Cl Cl -OC(=O)O- CH=CH2
CH2CH2CH3 H H -OC(=O)S- CH=CH2
CH2CH2CH3 CH3 H -OC(=O)S- CH=CH2
CH2CH2CH3 CH3 CH3 -OC(=O)S- CH=CH2
CH.,CH2CH3 CH3 CI -OC(=O)S- CH=CHI
CH2CH'CH3 CI CH3 -OC(=O)S- CH=CH2
CH~CH2CH3 C1 Cl -OC(=O)S- CH=CH2
CH3 H H -OC(=O)O- C(=CH2)CH3
CH3 CH3 H -OC(=O)O- C(=CH2)CH3 ,
CH3 CH3 CI-I3 -OC(=O)O- C(=CH2)CH3
CH3 CH3 CI -OC(=O)O- C(=CH2)CH3
CH3 Cl CH3 -OC(=O)O- C(=CH2)CH3
CH3 CI CI -OC(=O)O- C(=CH2)CH3
CH3 H H -OC(=O)S- C(=CH~)CH3
CH3 CH3 H -OC(=O)S- C(=CH2)CH3
CH3 CH3 CH3 -OC(=O)S- C(=CH~)CH3
CH3 CH3 CI -OC(=O)S- C(=CH2)CH3
CH3 CI CH3 -OC(=O)S- C(=CH2)CH3
CH3 CI CI -OC(=O)S- C(=CH')CH3
CH2CH3 H H -OC(=O)O- C(=CH2)CH3
CH2CH3 CH3 H -OC(=O)O- C(=CH2)CH3
CH2CH3 CH3 CH3 -OC{=O)O- C(=CH2)CH3
CH2CH3 CH3 Cl -OC(=O)O- C(=CH2)CH3
CH2CH3 CI CH3 -OC(=O)O- C(=CH2)CH3
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CH2CH3 C1 C1 -OC(=O)O- C(=CH2)CH3
CH2CH3 H H -OC(=O)S- C(=CH2)CH3
CH2CH3 CH3 H -OC(=O)S- C(=CH2)CH3
CH2CH3 CH3 CH3 -OC(=O)S- C(=CH2)CH3
CH2CH3 CH3 Cl -OC(=O)S- C(=CH2)CH3
CH2CH3 Cl CH3 -OC(=O)S- C(=CH2)CH3
CH2CH3 Cl Cl -OC{=O)S- C(=CH2)CH3
CH2CH2CH3 H H -OC(=O)O- C(=CH2)CH3
CH2CH2CH3 CH3 H -OC(=O)O- C(=CH2)CH3
CH2CH2CH3 CH3 CH3 -OC(=O)O- C(=CH2)CH3
CH2CH2CH3 CH3 Cl -OC(=O)O- C(=CH2)CH3
CH2CH2CH3 Cl CH3 -OC(=O)O- C(=CH2)CH3
CH2CH2CH3 Cl Cl -OC(=O)O- C(=CH2)CH3
CH2CH2CH3 H H -OC(=O)S- C(=CH2)CH3
CH2CH2CH3 CH3 H -OC(=O)S- C(=CH2)CH3
CH2CH2CH3 CH3 CH3 -OC(=O)S- C(=CH2)CH3
CH2CH2CH3 CH3 Cl -OC(=O)S- C(=CH2)CH3
CHZCHZCH3 Cl CH3 -OC(=O)S- C(=CH2)CH3
CH2CH2CH3 Cl Cl -OC(=O)S- C(=CH2)CH3
CH3 H H -OC(=O)O- CH2CH=CH2
CH3 CH3 H -OC(=O)O- CHZCH=CH2
CH3 CH3 CH3 -OC(=O)O- CH2CH=CH2
CH3 CH3 CI -OC(=O)O- CH2CH=CH2
CH3 Cl CH3 -OC(=O)O- CH2CH=CH2
CH3 Cl Cl -OC(=O)O- CH2CH=CH2
CH3 H H -OC(=O)S- CH2CH=CH2
CH3 CH3 H -OC(=O)S- CH~CH=CH2
CH3 CH3 CH3 -OC(=O)S- CH2CH=CH2
CH3 CH3 C1 -OC(=O)S- CH2CH=CH2
CH3 C1 CH3 -OC(=O)S- CH~CH=CH'
CH3 CI CI -OC(=O)S- CH2CH=CH2
CH2CH3 H H -OC(=O)O- CH2CH=CH2
CH2CH3 CH3 H -OC(=O)O- CH2CH=CH2
CH2CH3 CH3 CH3 -OC(=O)O- CH2CH=CH2
CH2CH3 CH3 Cl -OC(=O)O- CH~CH=CH2
CH2CH3 Cl CH3 -OC(=O)O- CH2CH=CHI
CH2CH3 Cl Cl -OC(=O)O- CH2CH=CH'
CH2CH3 . H H -OC(=O)S- CH~CH=CH2
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CH2CH3 CH3 H -OC(=O)S- CH2CH=CH2
CHZCH3 CH3 CH3 -OC{=O)S- CH2CH=CH2
CH2CH3 CH3 CI -OC(=O)S- CH2CH=CH2
CH2CH3 C1 CH3 -OC(=O)S- CH2CH=CH2
CH~CH3 CI Cl -OC(=O)S- CH2CH=CH2
CH2CH2CH3 H H -OC(=O)O- CH2CH=CH2
CH2CH2CH3 CH3 H -OC{=O)O- CH2CH=CH2
CH2CH2CH3 CH3 CH3 -OC(=O)O- CH2CH=CH2
CH2CH2CH3 CH3 CI -OC(=O)O- CH2CH=CH2
CH2CH2CH3 CI CH3 -OC(=O)O- CH2CH=CH2
CH2CH2CH3 CI Cl -OC(=O)O- CH2CH=CH2
CH2CH2CH3 H H -OC(=O)S- CH2CH=CH2
CH2CH~CH3 CH3 H -OC(=O)S- CH2CH=CH2
CH2CH2CH3 CH3 CH3 -OC(=O)S- CH2CH=CH2
CH2CH2CH3 CH3 Cl -OC(=O)S- CH2CH=CH2
CH2CH2CH3 C1 CH3. -OC(=O)S- CH2CH=CH2
CH2CH2CH3 C1 CI -OC(=O)S- CH2CH=CHZ
CH3 H H -OC(=O)O- CH=CHCH3
CH3 CH3 H -OC(=O)O- CH=CHCH3
CH3 CH3 CH3 -OC(=O)O- CH=CHCH3
CH3 CH3 Cl -OC(=O)O- CH=CHCH3
CH3 CI CH3 -OC(=O)O- CH=CHCH3
CH3 CI CI -OC(=O)O- CH=CHCH3
CH3 H H -OC(=O)S- CH=CHCH3
CH3 CH3 H -OC(=O)S- CH=CHCH3
CH3 CH3 CH3 -OC(=O)S- CH=CHCH3
CH3 CH3 CI -OC{=O)S- CH=CHCH3
CH3 CI CH3 -OC{=O)S- CH=CHCH3
CH3 CI Cl -OC(=O)S- CH=CHCH3
CH2CH3 H H -OC(=O)O- CH=CHCH3
CH2CH3 CH3 H -OC(=O)O- CH=CHCH3
CH2CH3 CH3 CH3 -OC(=O)O- CH=CHCH3
CH2CH3 CH3 Cl -OC{=O)O- CH=CHCH3
CH2CH3 Cl CH3 -OC{=O)O- CH=CHCH3
CH2CH3 CI CI -OC(=O)O- CH=CHCH3
CH2CH3 H H -OC{=O)S- CH=CHCH3
CH2CH3 CH3 H -OC{=O)S- CH=CHCH3
CH2CH3 CH3 CH3 -OC(=O)S- CH=CHCH3
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CH2CH3 CH3 Cl -OC(=O)S- CH=CHCH3
CH2CH3 Cl CH3 -OC(=O)S- CH=CHCH3
CH2CH3 CI Cl -OC(=O)S- CH=CHCH3
CH2CH2CH3 H H -OC(=O)O- CH=CHCH3
CH2CH2CH3 CH3 H -OC{=O)O- CH=CHCH3
CH2CH2CH3 CH3 CH3 -OC(=O)O- CH=CHCH3
CH2CH2CH3 CH3 Cl -OC(=O)O- CH=CHCH3
CH2CH2CH3 CI CH3 -OC(=O)O- CH=CHCH3
CH2CH2CH3 Cl C1 -OC(=O)O- CH=CHCH3
CH2CH2CH3 H H -OC{=O)S- CH=CHCH3
CH2CH2CH3 CH3 H -OC(=O)S- CH=CHCH3
CH2CH2CH3 CH3 CH3 -OC(=O)S- CH=CHCH3
CH2CH2CH3 CH3 Cl -OC(=O)S- CH=CHCH3
CH2CH2CH3 CI CH3 -OC(=O)S- CH=CHCH3
CH2CH2CH3 Cl Cl -OC(=O)S- CH=CHCH3
CH3 H H -OC(=O)O- phenyl
CH3 CH3 H -OC(=O)O- phenyl
CH3 CH3 CH3 -OC(=O)O- phenyl
CH3 CH3 Cl -OC(=O)O- phenyl
CH3 Cl CH3 -OC(=O)O- phenyl
CH3 CI Cl -OC(=O)O- phenyl
CH3 H H -OC(=O)S- phenyl
CH3 CH3 H -OC(=O)S- phenyl
CH3 CH3 CH3 -OC(=O)S- phenyl
CH3 CH3 CI -OC(=O)S- phenyl
CH3 Cl CH3 -OC(=O)S- phenyl
CH3 CI Cl -OC(=O)S- phenyl
CH2CH3 H H -OC(=O)O- phenyl
CH2CH3 CH3 H -OC(=O)O- phenyl
CH~CH3 CH3 CH3 -OC(=O)O- phenyl
CHZCH3 CH3 Cl -OC(=O)O- phenyl
CH2CH3 Cl CH3 -OC(=O)O- phenyl
CH2CH3 Cl CI -OC(=O)O- phenyl
CH2CH3 H H -OC(=O}S- phenyl
CH2CH3 CH3 H -OC(=O)S- phenyl
CH2CH3 CH3 CH3 -OC(=O)S- phenyl
CH2CH3 CH3 Cl -OC{=O)S- phenyl
CH2CH3 Cl CH3 -OC(=O)S- phenyl
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CHZCH3 Cl C1 -OC(=O)S- phenyl
CH2CH2CH3 H H -OC(=O)O- phenyl
CH2CH2CH3 CH3 H -OC(=O)O- phenyl
CH2CH2CH3 CH3 CH3 -OC(=O)O- phenyl
CH2CH2CH3 CH3 Cl -OC(=O)O- phenyl
CH2CH2CH3 Cl CH3 -OC(=O)O- phenyl
CH2CH2CH3 Cl Cl -OC(=O)O- phenyl
CH2CH2CH3 H H -OC(=O)S- phenyl
CH2CH~CH3 CH3 H -OC(=O)S- phenyl
CH2CH2CH3 CH3 CH3 -OC(=O)S- phenyl
CH2CH2CH3 CH3 Cl -OC(=O)S- phenyl
CH2CH~CH3 Cl CH3 -OC(=O)S- phenyl
CH2CH2CH3 Cl Cl -OC(=O)S- phenyl
CH3 H H -OC(=O)O- 2-pyridinyl
CH3 CH3 H -OC(=O)O- 2-pyridinyl
CH3 CH3 CH3 -OC(=O)O- 2-pyridinyl
CH3 CH3 Cl -OC(=O)O- 2-pyridinyl
CH3 Cl CH3 -OC(=O)O- 2-pyridinyl
CH3 Cl Cl -OC(=O)O- 2-pyridinyl
CH3 H H -OC(=O)S- 2-pyridinyl
CH3 CH3 H -OC(=O)S- 2-pyridinyl
CH3 CH3 CH3 -OC(=O)S- 2-pyridinyl
CH3 CH3 Cl -OC(=O)S- 2-pyridinyl
CH3 CI CH3 -OC(=O)S- 2-pyridinyl
CH3 Cl Cl -OC(=O)S- 2-pyridinyl
CH2CH3 H H -OC(=O)O- 2-pyridinyl
CH2CH3 CH3 H -OC(=O)O- 2-pyridinyl
CH~CH3 CH3 CH3 -OC(=O)O- 2-pyridinyl
CH2CH3 CH3 Cl -OC(=O)O- 2-pyridinyl
CH2CH3 CI CH3 -OC(=O)O- 2-pyridinyl
CH2CH3 Cl Cl -OC(=O)O- 2-pyridinyl
CH2CH3 H H -OC(=O)S- 2-pyridinyl
CH2CH3 CH3 H -OC(=O)S- 2-pyridinyl
CH2CH3 CH3 CH3 -OC(=O)S- 2-pyridinyl
CH2CH3 CH3 Cl -OC(=O)S- 2-pyridinyl
CH~CH3 Cl CH3 -OC(=O)S- 2-pyridinyl
CH~CH3 Cl Cl -OC(=O)S- 2-pyridinyl
CH2CH2CH3 H H -OC(=O)O- 2-pyridinyl
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CH2CH2CH3 CH3 H -OC(=O)O- 2-pyridinyl
CH2CH2CH3 CH3 CH3 -OC(=O)O- 2-pyridinyl
CH2CH2CH3 CH3 C1 -OC(=O)O- 2-pyridinyl
CH2CH2CH3 Cl CH3 -OC(=O)O- 2-pyridinyl
CH2CH2CH3 CI Cl -OC(=O)O- 2-pyridinyl
CH2CH2CH3 H H -OC(=O)S- 2-pyridinyl
CH2CH2CH3 CH3 H -OC(=O)S- 2-pyridinyl
CH2CH~CH3 CH3 CH3 -OC(=O)S- 2-pyridinyl
CH2CH2CH3 CH3 Cl -OC(=O)S- 2-pyridinyl
CH2CH2CH3 C1 CH3 -OC(=O)S- 2-pyridinyl
CH2CH2CH3 CI Cl -OC(=O)S- 2-pyridinyl
CH3 H H -OC(=O)O- 2-furanyl
CH3 CH3 H -OC(=O)O- 2-furanyl
CH3 CH3 CH3 -OC(=O)O- 2-furanyl
CH3 CH3 Cl -OC(=O)O- 2-furanyl
CH3 Cl CH3 -OC(=O)O- 2-furanyl
CH3 Cl Cl -OC(=O)O- 2-furanyl
CH3 H H -OC(=O)S- 2-furanyl
CH3 CH3 H -OC(=O)S- 2-furanyl
CH3 CH3 CHI -OC(=O)S- 2-furanyl
CH3 CH3 CI -OC(=O)S- 2-furanyl
CH3 CI CH3 -OC(=O)S- 2-furanyl
CH3 Cl C1 -OC(=O)S- 2-furanyl
CH2CH3 H H -OC(=O)O- 2-furanyl
CH2CH3 CH3 H -OC(=O)O- 2-furanyl
CH2CH3 CH3 CH3 -OC(=O)O- 2-furanyl
CH~CH3 CH3 Cl -OC(=O)O- 2-furanyl
CH2CH3 Cl CH3 -OC(=O)O- 2-furanyl
CH2CH3 Cl Cl -OC(=O)O- 2-furanyl
CH2CH3 H H -OC(=O)S- 2-furanyl
CH2CH3 CH3 H -OC{=O)S- 2-furanyl
CH2CH3 CH3 CH3 -OC(=O)S- 2-furanyl
CH2CH3 CH3 Cl -OC(=O)S- 2-furanyl
CH2CH3 Cl CH3 -OC(=O)S- 2-furanyl
CH2CH3 C1 Cl -OC(=O)S- 2-furanyl
CH2CH2CH3 H H -OC(=O)O- 2-furanyl
CH2CH2CH3 CH3 H -OC(=O)O- 2-furanyl
CH2CH~CH3 CH3 CH3 -OC(=O)O- 2-furanyl
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CH2CH2CH3 CH3 C1 -OC(=O)O- 2-furanyl
CH2CH2CH3 Cl CH3 -OC(=O)O- 2-furanyl
CH2CH2CH3 Cl Cl -OC(=O)O- 2-furanyl
CH2CH2CH3 H H -OC(=O)S- 2-furanyl
CH2CH~CH3 CH3 H -OC(=O)S- 2-furanyl
CH2CH2CH3 CH3 CH3 -OC(=O)S- 2-furanyl
CH2CH2CH3 CH3 Cl -OC(=O)S- 2-furanyl
CH2CH2CH3 Cl CH3 -OC(=O)S- 2-furanyl
CH2CH2CH3 Cl Cl -OC(=O)S- 2-furanyl
CH3 H H -OC(=O)O- 2-thienyl
CH3 CH3 H -OC(=O)O- 2-thienyl
CH3 CH3 CH3 -OC(=O)O- 2-thienyl
CH3 CH3 C1 -OC(=O)O- 2-thienyl
CH3 Cl CH3 -OC(=O)O- 2-thienyl
CH3 CI Cl -OC(=O)O- 2-thienyl
CH3 H H -OC(=O)S- 2-thienyl
CH3 CH3 H -OC(=O)S- 2-thienyl
CH3 CH3 CH3 -OC(=O)S- 2-thienyl
CH3 CH3 Cl -OC(=O)S- 2-thienyl
CH3 Cl CH3 -OC(=O)S- 2-thienyl
CH3 C1 Cl -OC(=O)S- 2-thienyl
CH2CH3 H H -OC(=O}O- 2-thienyl
CH2CH3 CH3 H -OC(=O)O- 2-thienyl
CH2CH3 CH3 CH3 -OC(=O)O- 2-thienyl
CH2CH3 CH3 CI -OC(=O)O- 2-thienyl
CH~CH3 Cl CH3 -OC(=O)O- 2-thienyl
CH2CH3 Cl Cl -OC(=O)O- 2-thienyl
CH2CH3 H H -OC(=O)S- 2-thienyl
CH2CH3 CH3 H -OC(=O}S- 2-thienyl
CH2CH3 CH3 CH3 -OC(=O)S- 2-thienyl
CH2CH3 CH3 CI -OC(=O)S- 2-thienyl
CH2CH3 C1 CH3 -OC(=O)S- 2-thienyl
CH2CH3 Cl C1 -OC(=O)S- 2-thienyl
CH2CH2CH3 H H -OC(=O)O- 2-thienyl
CH2CH2CH3 CH3 H -OC(=O)O- 2-thienyl
CH2CH2CH3 CH3 CH3 -OC(=O)O- 2-thienyl
CH2CHZCH3 CH3 Cl -OC(=O)O- 2-thienyl
CH2CHZCH3 Cl CH3 -OC(=O)O- 2-thienyl
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CH2CH2CH3 C1 Cl -OC(=O)O- 2-thienyl
CHZCH2CH3 H H -OC(=O)S- 2-thienyl
CH2CH~CH3 CH3 H -OC(=O)S- 2-thienyl
CH2CHZCH3 CH3 CH3 -OC(=O)S- 2-thienyl
CH2CH~CH3 CH3 Cl -OC(=O)S- 2-thienyl
CH2CH2CH3 Cl CH3 -OC(=O)S- 2-thienyl
CH,CH2CH3 C1 Cl -OC(=O)S- 2-thienyl
CH3 H H -OC(=O)- CH3
CH3 CH3 H -OC(=O)- CH3
CH3 CH3 CH3 -OC(=O)- CH3
CH3 CH3 Cl -OC(=O)- CH3
CH3 C1 CH3 -OC(=O)- CH3
CH3 CI CI -OC(=O)- CH3
CH2CH3 H H -OC(=O)- CH3
CH2CH3 CH3 H -OC(=O)- CH3
CHZCH3 CH3 CH3 -OC(=O)- CH3
CH2CH3 CH3 CI -OC(=O)- CH3
CH~CH3 CI CH3 -OC(=O)- CH3
CH2CH3 CI CI -OC(=O)- CH3
CH2CH2CH3 H H -OC(=O)- CH3
CH2CH~CH3 CH3 H -OC(=O)- CH3
CH2CH2CH3 CH3 CHI -OC(=O)- CH3
CH2CH~CH3 CH3 C1 -OC(=O)- CH3
CH2CH2CH3 Cl CH3 -OC(=O)- CH3
CH2CH~CH3 Cl Cl -OC(=O)- CH3
CH3 H H -OC(=O)- CH2CH3
CH3 CH3 H -OC(=O)- CH~CH3
CH3 CH3 CH3 -OC(=O}- CH2CH3
CH3 CH3 C1 -OC(=O)- CH~CH3
CH3 Cl CHI -OC(=O)- CH2CH3
CH3 C1 Cl -OC(=O)- CH2CH3
CH2CH3 H H -OC(=O)- CH2CH3
CH2CH3 CH3 H -OC(=O)- CH2CH3
CH2CH3 CH3 CH3 -OC(=O}- CH2CH3
CH2CH3 CH3 Cl -OC(=O)- CH2CH3
CH2CH3 CI CH3 -OC(=O)- CH2CH3
CH2CH3 C1 C1 -OC(=O)- CI-12CH3
CH2CHZCH3 H H -OC(=O)- CH~CH3
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CH2CH2CH3 CH3 H -OC(=O)- CH2CH3
CH2CH2CH3 CH3 CH3 -OC(=O)- CH2CH3
CH2CH2CH3 CH3 Cl -OC{=O)- CH2CH3
CH2CH2CH3 Cl CH3 -OC(=O)- CH2CH3
CH2CH2CH3 Cl Cl -OC(=O)- CH2CH3
CH3 H H -OC(=O)- CH2CH2CH3
CH3 CH3 H -OC(=O)- CHZCH2CH3
CH3 CH3 CH3 -OC(=O)- CH2CH2CH3
CH3 CH3 CI -OC(=O)- CH2CH2CH3
CH3 Cl CH3 -OC(=O)- CH2CH2CH3
CH3 Cl Cl -OC(=O)- CH2CH2CH3
CH2CH3 H H -OC(=O)- CH2CH2CH3
CH2CH3 CH3 H -OC(=O)- CH2CH2CH3
CH2CH3 CH3 CH3 -OC(=O)- CH~CH2CH3
CH2CH3 CH3 Cl -OC(=O)- CH2CH2CH3
CH2CH3 C1 CH3 -OC(=O)- CHzCH2CH3
CH2CH3 Cl C1 -OC(=O)- CH2CH2CH3
CH~CH2CH3 H H -OC(=O)- CH~CH2CH3
CH2CH2CH3 CH3 H -OC(=O)- CH~CH2CH3
CH2CHZCH3 CH3 CH3 -OC(=O)- CH~CH2CH3
CH2CH2CH3 CH3 C1 -OC(=O)- CH2CH2CH3
CH2CH2CH3 C1 CH3 -OC(=O)- CH2CH~CH3
CH2CH2CH3 CI C1 -OC(=O)- CH2CH2CH3
CH3 H H -OC(=O)- cyclo-propyl
CH3 CH3 H -OC(=O)- cyclo-propyl
CH3 CH3 CH3 -OC(=O)- cyclo-propyl
CH3 CH3 Cl -OC(=O)- cyclo-propyl
CH3 Cl CH3 -OC{=O)- cyclo-propyl
CH3 Cl Cl -OC(=O)- cyclo-propyl
CH2CH3 H H -OC(=O)- cyclo-propyl
CH2CH3 CH3 H -OC(=O)- cyclo-propyl
CH2CH3 CH3 CH3 -OC(=O)- cyclo-propyl
CH2CH3 CH3 Cl -OC(=O)- cyclo-propyl
CH2CH3 C1 CH3 -OC(=O)- cyclo-propyl
CH2CH3 Cl Cl -OC(=O)- cyclo-propyl
CH2CH2CH3 H H -OC(=O)- cyclo-propyl
CH2CH2CH3 CH3 H -OC{=O)- cyclo-propyl
CH2CH2CH3 CH3 CH3 -OC(=O)- cyclo-propyl
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CH2CH2CH3 CH3 Cl -OC(=O)- cyclo-propyl
CH2CHZCH3 Cl CH3 -OC{=O)- cyclo-propyl
CH2CH2CH3 CI Cl -OC(=O)- cyclo-propyl
CH3 H H -OC(=O)- CH=CH2
CH3 CH3 H -OC(=O)- CH=CH2
CH3 CH3 CH3 -OC(=O)- CH=CH2
CH3 CH3 CI -OC(=O)- CH=CH2
CH3 Cl CH3 -OC(=O)- CH=CH2
CH3 CI CI -OC(=O)- CH=CH2
CH2CH3 H H -OC(=O)- CH=CH2
CH,CH3 CH3 H -OC(=O)- CH=CH2
CH2CH3 CH3 CH3 -OC(=O)- CH=CH2
CH2CH3 CH3 Cl -OC(=O)- CH=CH2
CH2CH3 Cl CH3 -OC(=O)- CH=CH2
CH2CH3 CI CI -OC(=O)- CH=CH2
CH2CH2CH3 H H -OC(=O)- CH=CH2
CH2CH2CH3 CH3 H -OC(=O)- CH=CH2
CH2CH2CH3 CH3 CH3 -OC{=O)- CH=CH2
CH2CH2CH3 CH3 Cl -OC(=O)- CH=CH2
CH~CH2CH3 CI CH3 -OC(=O}- CI-I=CH2
CH2CH2CH3 CI CI -OC(=O)- CH=CHI
CH3 H H -OC(=O)- C(=CH2)CH3
CH3 CH3 H -OC(=O)- C(=CH2)CH3
CH3 CH3 CH3 -OC(=O)- C(=CH2)CH3
CH3 CH3 Cl -OC(=O)- C(=CH2)CH3
CH3 Cl CH3 -OC(=O)- C(=CH2)CH3
CH3 Cl CI -OC(=O)- C(=CH2)CH3
CH2CH3 H H -OC(=O)- C(=CH2)CH3
CH2CH3 CH3 H -OC(=O)- C(=CHZ)CH3
CH2CH3 CH3 CH3 -OC(=O)- C(=CHZ)CH3
CH2CH3 CH3 CI -OC(=O)- C(=CH2)CH3
CH2CH3 Cl CH3 -OC(=O)- C(=CH2)CH3
CH2CH3 Cl C1 -OC(=O)- C(=CH2)CH3
CH~CH2CH3 H H -OC(=O)- C(=CH2)CH3
CH2CH2CH3 CH3 H -OC(=O)- C(=CH2)CH3
CH2CH2CH3 CH3 CH3 -OC(=O)- C(=CH2)CH3
CH2CH~CH3 CH3 Cl -OC(=O)- C(=CH2)CH3
CH2CH~CH3 C1 CH3 -OC(=O)- C(=CH2)CH3
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CH2CH~CH3 CI C1 -OC(=O)- C(=CH2)CH3
CH3 H H -OC(=O)- CHZCH=CH2
CH3 CH3 H -OC(=O)- CH2CH=CHI
CH3 CH3 CH3 -OC(=O)- CH2CH=CH2
CH3 CH3 Cl -OC(=O)- CH2CH=CHI
CH3 Cl CH3 -OC(=O)- CH2CH=CH2
CH3 C1 Cl -OC(=O)- CHZCH=CH2
CH2CH3 H H -OC(=O)- CH2CH=CH2
CH~CH3 CH3 H -OC{=O)- CHZCH=CH2
CH2CH3 CH3 CH3 -OC(=O}- CH2CH=CH2
CH~CH3 CH3 Cl -OC(=O)- CH~CH=CH2
CH2CH3 C1 CH3 -OC(=O)- CH2CH=CH2
CH2CH3 Cl Cl -OC(=O}- CH2CH=CH2
CH2CH2CH3 H H -OC(=O)- CH2CH=CH2
CH2CH2CH3 CH3 H -OC(=O)- CH2CH=CH2
CH2CH2CH3 CH3 CH3 -OC(=O)- CH2CH=CH2
CH~CH'CH3 CH3 CI -OC(=O}- CH2CH=CH2
CH2CH~CH3 Cl CH3 -OC(=O)- CH2CH=CH2
CH~CH2CH3 Cl Cl -OC{=O)- CH2CH=CHI
CH3 H H -OC(=O)- CH=CHCH3
CH3 CH3 H -OC(=O)- CH=CHCH3
CH3 CH3 CH3 -OC(=O}- CH=CHCH3
CH3 CH3 Cl -OC(=O)- CH=CHCH3
CH3 Cl CH3 -OC(=O)- CH=CHCH3
CH3 CI Cl -OC(=O)- CH=CHCH3
CH2CH3 H H -OC(=O)- CH=CHCH3
CH2CH3 CH3 H -OC(=O)- CH=CHCH3
CH2CH3 CH3 CH3 -OC(=O)- CH=CHCH3
CH2CH3 CH3 Cl -OC{=O)- CH=CHCH3
CH2CH3 Cl CH3 -OC(=O)- CH=CHCH3
CH2CH3 C1 Cl -OC(=O)- CH=CHCH3
CH2CH2CH3 H H -OC(=O)- CH=CHCH3
CH2CH~CH3 CH3 H -OC(=O}- CH=CHCH3
CH2CH2CH3 CH3 CH3 -OC(=O)- CH=CHCH3
CH2CH2CH3 CH3 Cl -OC(=O)- CH=CHCH3
CH~CH~CH3 Cl CHI -OC(=O)- CH=CHCH3
CH2CH~CH3 Cl Cl -OC(=O)- CH=CHCH3
CH3 H H -OC(=O)- phenyl
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CH3 CH3 H -OC(=O)- phenyl
CH3 CH3 CH3 -OC{=O)- phenyl
CH3 CH3 CI -OC(=O)- phenyl
CH3 CI CH3 -OC(=O)- phenyl
CH3 Cl C1 -OC(=O)- phenyl
CH2CH3 H H -OC(=O)- phenyl
CH2CH3 CH3 H -OC(=O)- phenyl
CH~CH3 CH3 CH3 -OC(=O)- phenyl
CH2CH3 CH3 C1 -OC(=O)- phenyl
CH2CH3 C1 CH3 -OC(=O)- phenyl
CH2CH3 Cl Cl -OC(=O)- phenyl
CHZCH2CH3 H H -OC(=O)- phenyl
CH2CH~CH3 CH3 H -OC(=O)- phenyl
CH2CH2CH3 CH3 CH3 -OC(=O)- phenyl
CH2CH2CH3 CH3 CI -OC(=O)- phenyl
CH~CH~CH3 Cl CH3 -OC(=O)- phenyl
CH2CH2CH3 C1 Cl -OC(=O)- phenyl
CH3 H H -OC(=O)- 2-pyridinyl
CH3 CH3 H -OC(=O)- 2-pyridinyl
CH3 CH3 CH3 -OC(=O)- 2-pyridinyl
CH3 CH3 CI -OC(=O)- 2-pyridinyl
CH3 CI CH3 -OC(=O)- 2-pyridinyl
CH3 CI C1 -OC(=O)- 2-pyridinyl
CH2CH3 H H -OC(=O)- 2-pyridinyl
CH~CH3 CH3 H -OC(=O)- 2-pyridinyl
CH2CH3 CH3 CH3 -OC(=O)- 2-pyridinyl
CH2CH3 CH3 Cl -OC(=O)- 2-pyridinyl
CH2CH3 C1 CH3 -OC(=O)- 2-pyridinyl
CH2CH3 C1 C1 -OC(=O)- 2-pyridinyl
CH~CH2CH3 H H -OC(=O)- 2-pyridinyl
CH2CH2CH3 CH3 H -OC(=O)- 2-pyridinyl
CH2CH2CH3 CH3 CH3 -OC(=O)- 2-pyridinyl
CH2CH2CH3 CH3 Cl -OC(=O)- 2-pyridinyl
CH2CH2CH3 CI CH3 -OC(=O)- 2-pyridinyl
CH2CH2CH3 C1 CI -OC(=O)- 2-pyridinyl
CH3 H H -OC(=O)- 2-furanyl
CH3 CH3 H -OC(=O)- 2-furanyl
CH3 CH3 CH3 -OC(=O)- 2-furanyl
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CH3 CH3 Cl -OC(=O}- 2-furanyl
CH3 Cl CH3 -OC(=O)- 2-furanyl
CH3 Cl CI -OC(=O)- 2-furanyl
CH2CH3 H H -OC(=O)- 2-furanyl
CH~CH3 CH3 H -OC(=O)- 2-furanyl
CH2CH3 CH3 CH3 -OC(=O)- 2-furanyl
CHzCH3 CH3 CI -OC(=O)- 2-furanyl
CH~CH3 Cl CH3 -OC(=O)- 2-furanyl
CH2CH3 CI Cl -OC(=O)- 2-furanyl
CH2CH2CH3 H H -OC(=O)- 2-furanyl
CH2CH2CH3 CH3 H -OC(=O)- 2-furanyl
CH2CH2CH3 CH3 CH3 -OC(=O)- 2-furanyl
CH2CH2CH3 CH3 Cl -OC{=O)- 2-furanyl
CH~CH2CH3 C1 CH3 -OC(=O)- 2-furanyl
CH2CH2CH3 Cl Cl -OC(=O)- 2-furanyl
CH3 H H -OC(=O}- 2-thienyl
CH3 CH3 H -OC(=O}- 2-thienyl
CH3 CH3 CH3 -OC(=O)- 2-thienyl
CH3 CH3 Cl -OC(=O)- 2-thienyl
CH3 CI CH3 -OC(=O)- 2-thienyl
CH3 C1 Cl -OC(=O)- 2-thienyl
CH2CH3 H H -OC(=O)- 2-thienyl
CH2CH3 CH3 H -OC(=O)- 2-thienyl
CH2CH3 CH3 CH3 -OC(=O)- 2-thienyl
CH2CH3 CH3 CI -OC(=O)- 2-thienyl
CH2CH3 C1 CH3 -OC(=O}- 2-thienyl
CHZCH3 C1 CI -OC(=O)- 2-thienyl
CH~CH2CH3 H H -OC(=O)- 2-thienyl
CH2CH2CH3 CH3 H -OC(=O)- 2-thienyl
CH2CH2CH3 CH3 CH3 -OC(=O)- 2-thienyl
CH~CH2CH3 CH3 C1 -OC(=O)- 2-thienyl
CH2CH2CH3 C1 CH3 -OC(=O)- 2-thienyl
CH2CH2CH3 CI Cl -OC(=O)- 2-thienyl
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Table 2
R
~r
RI R2 R3 A Q
CH3 H H -OC(=O)O- CH3
CH3 CH3 H -OC(=O)O- CH3
CH3 CH3 CH3 -OC(=O)O- CH3
CH3 CH3 CI -OC(=O)O- CH3
CH3 CI CH3 -OC(=O)O- CH3
CH3 CI CI -OC(=O)O- CH3
CH3 H H -OC(=O)S- CH3
CH3 CH3 H -OC(=O)S- CH3
CH3 CH3 CH3 -OC(=O)S- CH3
CH3 CH3 Cl -OC(=O)S- CH3
CH3 C1 CH3 -OC(=O)S- CH3
CH3 CI Cl -OC{=O)S- CH3
CH2CH3 H H -OC(=O)O- CH3
CH2CH3 CH3 H -OC(=O)O- CH3
CH2CH3 CH3 CH3 -OC(=O)O- CH3
CH2CH3 CH3 CI -OC(=O)O- CH3
CH2CH3 Cl CH3 -OC(=O)O- CH3
CH2CH3 CI Cl -OC(=O)O- CH3
CHZCH3 H H -OC(=O)S- CH3
CH2CH3 CH3 H -OC(=O)S- CH3
CH2CH3 CH3 CH3 -OC(=O)S- CH3
CH2CH3 CH3 CI -OC(=O)S- CH3
CH2CH3 Cl CH3 -OC(=O)S- CH3
CH2CH3 CI Cl -OC(=O)S- CH3
CH2CH2CH3 H H -OC(=O)O- CH3
CH2CH2CH3 CH3 H -OC(=O)O- CH3
CH2CH2CH3 CH3 CH3 -OC(=O)O- CH3
CH2CH2CH3 CH3 Cl -OC(=O)O- CH3
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CH2CH2CH3 CI CH3 -OC(=O)O- CH3
CH2CH2CH3 C1 Cl -OC(=O}O- CH3
CH2CH2CH3 H H -OC(=O)S- CH3
CH2CH2CH3 CH3 H -OC(=O)S- CH3
CH2CH2CH3 CH3 CH3 -OC(=O)S- CH3
CH2CH2CH3 CH3 CI -OC(=O)S- CH3
CH2CH2CH3 Cl CH3 -OC(=O)S- CH3
CH2CH2CH3 CI Cl -OC(=O)S- CH3
CH3 H H -OC(=O)O- CH2CH3
CH3 CH3 H -OC(=O)O- CH2CH3
CH3 CH3 CH3 -OC(=O)O- CH~CH3
CH3 CH3 CI -OC(=O)O- CH2CH3
CH3 CI CH3 -OC(=O)O- CH2CH3
CH3 Cl CI -OC(=O)O- CH2CH3
CH3 H H -OC(=O)S- CHZCH3
CH3 CH3 H -OC(=O}S- CH2CH3
CH3 CH3 CH3 -OC(=O)S- CH~CH3
CH3 CH3 C1 -OC(=O}S- CH2CH3
CH3 CI CH3 -OC(=O)S- CH2CH3
CH3 CI CI -OC(=O)S- CH2CH3
CH2CH3 H H -OC(=O)O- CH2CH3
CH2CH3 CH3 H -OC(=O)O- CH2CH3
CH2CH3 CH3 CH3 -OC(=O)O- CH~CH3
CH2CH3 CH3 Cl -OC(=O)O- CH~CH3
CH2CH3 CI CH3 -OC(=O)O- CH2CH3
CH2CH3 CI Cl -OC(=O)O- CH2CH3
CH2CH3 H H -OC(=O}S- CH~CH3
CH2CH3 CH3 H -OC(=O)S- CH2CH3
CH2CH3 CH3 CH3 -OC(=O)S- CH~CH3
CH2CH3 CH3 CI -OC(=O)S- CH2CH3
CH2CH3 CI CH3 -OC(=O)S- CH~CH3
CH2CH3 Cl CI -OC(=O)S- CHZCH3
CH-,CH2CH3 H H -OC(=O)O- CH2CH3
CH2CH2CH3 CH3 H -OC(=O)O- CH2CH3
CH~CH2CH3 CH3 CH3 -OC(=O)O- CH2CH3
CH2CH2CH3 CH3 Cl -OC(=O)O- CH,CH3
CH2CH2CH3 CI CH3 -OC(=O)O- CH~CH3
CH2CH2CH3 CI C1 -OC(=O)O- CH~CH3
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CH2CH2CH3 H H -OC(=O)S- CH2CH3
CHZCH2CH3 CH3 H -OC(=O)S- CH2CH3
CH2CH2CH3 CH3 CH3 -OC(=O)S- CH2CH3
CH2CH2CH3 CH3 Cl -OC(=O)S- CH2CH3
CH2CH2CH3 CI CH3 -OC(=O)S- CH2CH3
CH2CH2CH3 CI CI -OC(=O)S- CH2CH3
CH3 H H -OC(=O)O- CH2CH2CH3
CH3 CH3 H -OC(=O)O- CH2CH2CH3
CH3 CH3 CH3 -OC(=O)O- CH2CH2CH3
CH3 CH3 Cl -OC(=O)O- CH2CH2CH3
CH3 Cl CH3 -OC(=O)O- CH2CH2CH3
CH3 CI CI -OC(=O)O- CH2CH2CH3
CH3 H H -OC(=O)S- CH2CH2CH3
CH3 CH3 H -OC(=O)S- CH2CH2CH3
CH3 CH3 CH3 -OC(=O)S- CH2CH2CH3
CH3 CH3 CI -OC(=O)S- CH2CH2CH3
CH3 Cl CH3 -OC(=O)S- CH2CH2CH3
CH3 CI Cl -OC(=O)S- CH2CH2CH3
CH2CH3 H H -OC(=O)O- CH2CH2CH3
CH2CH3 CH3 H -OC{=O)O- CH2CH~CH3
CH2CH3 CH3 CH3 -OC(=O)O- CH2CH2CH3
CH2CH3 CH3 Cl -OC(=O)O- CH~CH2CH3
CH2CH3 Cl CH3 -OC(=O)O- CH2CH2CH3
CH2CH3 C1 CI -OC(=O)O- CH~CH2CH3
CH2CH3 H H -OC(=O)S- CH~CH2CH3
CH2CH3 CH3 H -OC(=O)S- CH2CH~CH3
CH2CH3 CH3 CH3 -OC(=O)S- CH~CH2CH3
CH2CH3 CH3 CI -OC(=O)S- CH2CH~CH3
CH~CH3 CI CH3 -OC(=O)S- CH2CH2CH3
CH2CH3 CI Cl -OC(=O)S- CI-12CH2CH3
CH~CH2CH3 H H -OC(=O)O- CH2CH2CH3
CH2CH2CH3 CH3 H -OC{=O)O- CH2CH2CH3
CH~CH2CH3 CH3 CH3 -OC(=O)O- CH2CH2CH3
CH2CH2CH3 CH3 CI -OC(=O)O- CH2CH2CH3
CH2CH2CH3 Cl CH3 -OC(=O)O- CH~CH2CH3
CH2CH2CH3 C1 CI -OC(=O)O- CH2CH2CH3
CH2CH2CH3 H H -OC(=O)S- CH2CH2CH3
CH,CH2CH3 CH3 H -OC(=O)S- CH2CH~CH3
.
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CH2CH2CH3 CH3 CH3 -OC(=O)S- CH2CH2CH3
CH2CH2CH3 CH3 Cl -OC(=O)S- CH2CH2CH3
CH2CH~CH3 Cl CH3 -OC(=O)S- CH~CH2CH3
CH2CH2CH3 Cl C1 -OC(=O)S- CH2CH2CH3
CH3 H H -OC(=O)O- cyclo-propyl
CH3 CH3 H -OC(=O)O- cyclo-propyl
CH3 CH3 CH3 -OC(=O)O- cvclo-propyl
CH3 CH3 Cl -OC(=O}O- cyclo-propyl
CH3 Cl CH3 -OC(=O)O- cyclo-propyl
CH3 CI C1 -OC(=O)O- cyclo-propyl
CH3 H H -OC(=O)S- cyclo-propyl
CH3 CH3 H -OC(=O)S- cyclo-propyl
CH3 CH3 CH3 -OC(=O)S- cvclo-propyl
CH3 CH3 Cl -OC(=O)S- cyclo-propyl
CH3 CI CH3 -OC(=O)S- cyclo-propyl
CH3 Cl C1 -OC(=O)S- cyclo-propyl
CH2CH3 H H -OC(=O)O- cyclo-propyl
CH2CH3 CH3 H -OC(=O)O- cyclo-propyl
CH2CH3 CH3 CH3 -OC(=O)O- cyclo-propyl
CH2CH3 CH3 Cl -OC(=O)O- cyclo-propyl
CH2CH3 CI CH3 -OC(=O}O- cyclo-propyl
CH2CH3 Cl Cl -OC(=O)O- cyclo-propyl
CH2CH3 H H -OC(=O)S- cyclo-propyl
CH2CH3 CH3 H -OC(=O)S- cyclo-propyl
CH~CH3 CH3 CH3 -OC(=O)S- cvclo-propyl
CH2CH3 CH3 Cl -OC{=O)S- cyclo-propyl
CH2CH3 CI CH3 -OC(=O)S- cyclo-propyl
CH2CH3 Cl Cl -OC(=O)S- cvclo-propyl
CH2CH2CH3 H H -OC(=O)O- cyclo-propyl
CH2CH2CH3 CH3 H -OC{=O)O- cyclo-propyl
CH2CH2CH3 CH3 CH3 -OC{=O)O- cyclo-propyl
CH2CH2CH3 CH3 C1 -OC(=O)O- cyclo-propyl
CH2CH2CH3 C1 CH3 -OC(=O)O- cyclo-propyl
CH2CH2CH3 C1 C1 -OC(=O)O- cyclo-propyl
CHZCH2CH3 H H -OC(=O)S- cyclo-propyl
CH~CH2CH3 CH3 H -OC(=O)S- cyclo-propyl
CH~CH2CH3 CH3 CH3 -OC(=O)S- cyclo-propyl
CH2CH2CH3 CH3 Cl -OC(=O)S- cyclo-propyl
_
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CH2CH2CH3 C1 CH3 -OC(=O)S- cvclo-propyl
CH2CH2CH3 CI Cl -OC(=O)S- cyclo-propyl
CH3 H H -OC(=O)O- CH=CH2
CH3 CH3 H -OC(=O)O- CH=CH2
CH3 CH3 CH3 -OC(=O)O- CH=CH2
CH3 CH3 Cl -OC(=O)O- CH=CH2
CH3 CI CH3 -OC(=O)O- CH=CH2
CH3 Cl Cl -OC(=O)O- CH=CH2
CH3 H H -OC(=O)S- CH=CH2
CH3 CH3 H -OC{=O)S- CH=CH2
CH3 CH3 CH3 -OC(=O)S- CH=CH2
CH3 CH3 Cl -OC(=O)S- CH=CH2
CH3 Cl CH3 -OC(=O)S- CH=CH2
CH3 CI Cl -OC(=O)S- CH=CH2
CH2CH3 H H -OC(=O)O- CH=CH2
CH2CH3 CH3 H -OC(=O)O- CH=CH2
CH2CH3 CH3 CH3 -OC(=O)O- CH=CH2
CH2CH3 CH3 CI -OC(=O)O- CH=CH2
CH2CH3 CI CH3 -OC(=O)O- CH=CH2
CH~CH3 Cl Cl -OC(=O)O- CH=CH2
CH2CH3 H H -OC(=O)S- CH=CH2
CH2CH3 CH3 H -OC(=O)S- CH=CH2
CH2CH3 CH3 CH3 -OC(=O)S- CI-I=CH2
CH2CH3 CH3 CI -OC(=O)S- CH=CH2
CH2CH3 Cl CH3 -OC(=O)S- CH=CH2
CH2CH3 C1 CI -OC{=O)S- CH=CHI
CH2CH2CH3 H H -OC(=O)O- CH=CHI
CH2CH~CH3 CH3 H -OC(=O)O- CH=CH2
CH2CH2CH3 CH3 CH3 -OC(=O)O- CH=CH2
CH2CH2CH3 CH3 C1 -OC(=O)O- CH=CH2
CHZCH2CH3 Cl CH3 -OC(=O)O- CH=CH2
CH2CH2CH3 CI Cl -OC(=O)O- CH=CHI
CH2CH~CH3 H H -OC(=O)S- CH=CH'
CH2CH~CH3 CH3 H -OC(=O)S- CH=CH2
CH2CH2CH3 CH3 CH3 -OC(=O)S- CH=CH2
CH2CH2CH3 CH3 C1 -OC(=O)S- CH=CHI
CH2CH2CH3 CI CH3 -OC(=O)S- CH=CH2
CH2CH~CH3 CI CI -OC(=O)S- CH=CHI
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CH3 H H -OC(=O)O- C(=CH2)CH3
CH3 CH3 H -OC(=O)O- C(=CH2)CH3
CH3 CH3 CH3 -OC(=O)O- C(=CH2)CH3
CH3 CH3 CI -OC(=O)O- C(=CH2)CH3
CH3 CI CH3 -OC(=O)O- C(=CH2)CH3
CH3 CI CI -OC(=O)O- C(=CH2)CH3
CH3 H H -OC(=O)S- C(=CH2)CH3
CH3 CH3 H -OC{=O)S- C(=CH2)CH3
CH3 CH3 CH3 -OC(=O)S- C(=CH2)CH3
CH3 CH3 Cl -OC(=O)S- C(=CH2)CH3
CH3 CI CH3 -OC(=O)S- C(=CH2)CH3
CH3 CI Cl -OC(=O)S- C(=CH2)CH3
CH2CH3 H H -OC(=O)O- C(=CH2)CH3
CH2CH3 CH3 H -OC(=O)O- C(=CH2)CH3
CH2CH3 CH3 CH3 -OC(=O)O- C(=CH2}CH3
CH2CH3 CH3 CI -OC(=O)O- C(=CH2)CH3
CH2CH3 Cl CH3 -OC(=O)O- C(=CH~)CH3
CH2CH3 Cl CI -OC(=O)O- C(=CH2)CH3
CH2CH3 H H -OC(=O)S- C(=CH2)CH3
CH2CH3 CH3 H -OC(=O)S- C(=CH2)CH3
CH2CH3 CH3 CH3 -OC(=O)S- C(=CH2)CH3
CH2CH3 CH3 Cl -OC(=O)S- C(=CH2)CH3
CH2CH3 CI CH3 -OC(=O)S- C(=CH2)CH3
CH2CH3 CI Cl -OC(=O}S- C(=CH2)CH3
CH2CH2CH3 H H -OC(=O)O- C(=CH2)CH3
CH2CH2CH3 CH3 H -OC(=O)O- C(=CH2)CH3
CH2CHZCH3 CH3 CH3 -OC(=O)O- C(=CH2)CH3
CH2CH2CH3 CH3 CI -OC(=O}O- C(=CH2)CH3
CH2CH2CH3 Cl CH3 -OC(=O)O- C(=CH2)CH3
CH2CH2CH3 Cl CI -OC(=O)O- C(=CH2)CH3
CH2CH2CH3 H H -OC(=O)S- C(=CH2)CH3
CH2CH2CH3 CH3 H -OC(=O)S- C(=CH2)CH3
CH2CH2CH3 CH3 CH3 -OC(=O)S- C(=CH2)CH3
CH2CH2CH3 CH3 CI -OC(=O)S- C(=CH2)CH3
CH2CH2CH3 CI CH3 -OC(=O)S- C(=CH2)CH3
CH2CH2CH3 CI CI -OC(=O)S- C(=CH2)CH3
CH3 H H -OC(=O)O- CH~CH=CH2
CH3 CH3 H -OC(=O)O- CH2CH=CH2
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CH3 CH3 CH3 -OC(=O)O- CH2CH=CH2
CH3 CH3 CI -OC(=O)O- CH2CH=CH2
CH3 CI CH3 -OC(=O)O- CH2CH=CH2
CH3 C1 CI -OC(=O)O- CH2CH=CH2
CH3 H H -OC(=O)S- CH2CH=CH2
CH3 CH3 H -OC(=O)S- CH2CH=CH2
CH3 CH3 CH3 -OC(=O)S- CH2CH=CH2
CH3 CH3 CI -OC(=O)S- CH2CH=CH2
CH3 CI CH3 -OC(=O)S- CH2CH=CHZ
CH3 CI Cl -OC(=O)S- CH2CH=CH2
CH2CH3 H H -OC(=O)O- CH2CH=CH2
CH~CH3 CH3 H -OC(=O)O- CH2CH=CH2
CH2CH3 CH3 CH3 -OC(=O)O- CH2CH=CHI
CH2CH3 CH3 CI -OC(=O)O- CH2CH=CH2
CH2CH3 Cl CH3 -OC(=O)O- CH2CH=CH2
CH2CH3 Cl CI -OC(=O)O- CH2CH=CH2
CH2CH3 H H -OC(=O)S- CH2CH=CH2
CH2CH3 CH3 H -OC(=O)S- CH2CH=CH2
CH2CH3 CH3 CH3 -OC(=O)S- CH2CH=CH2
CH2CH3 CH3 Cl -OC(=O)S- CH2CH=CH2
CH2CH3 Cl CH3 -OC(=O)S- CH2CH=CH2
CH2CH3 Cl CI -OC(=O)S- CH~CH=CH2
CH2CH2CH3 H H -OC(=O)O- CH2CH=CH2
CH2CH2CH3 CH3 H -OC(=O)O- CHZCH=CH2
CH2CH2CH3 CH3 CH3 -OC(=O)O- CH2CH=CHI
CH2CH2CH3 CH3 CI -OC{=O)O- CHZCH=CH2
CH2CH~CH3 Cl CH3 -OC(=O)O- CH2CH=CH2
CH2CH~CH3 CI CI -OC(=O)O- CH2CH=CH2
CH2CH2CH3 H H -OC(=O)S- CH2CH=CH2
CH2CH~CH3 CH3 H -OC(=O)S- CH2CH=CHI
CH2CH2CH3 CH3 CH3 -OC(=O)S- CH'CH=CH2
CH2CH2CH3 CH3 CI -OC(=O)S- CH2CH=CH2
CH2CH2CH3 CI CH3 -OC(=O)S- CH2CH=CHI
CH2CH2CH3 CI CI -OC{=O)S- CH~CH=CHI
CH3 H H -OC(=O)O- CH=CHCH3
CH3 CH3 H -OC(=O)O- CH=CHCH3
CH3 CH3 CH3 -OC(=O)O- CH=CHCH3
CH3 CH3 Cl -OC(=O)O- CH=CHCH3
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CH3 Cl CH3 -OC(=O)O- CH=CHCH3
CH3 CI Cl -OC(=O)O- CH=CHCH3
CH3 H H -OC(=O)S- CH=CHCH3
CH3 CH3 H -OC(=O)S- CH=CHCH3
CH3 CH3 CH3 -OC(=O)S- CH=CHCH3
CH3 CH3 CI -OC{=O)S- CH=CHCH3
CH3 Cl CH3 -OC(=O)S- CH=CHCH3
CH3 CI Cl -OC(=O)S- CH=CHCH3
CH2CH3 H H -OC(=O)O- CH=CHCH3
CH2CH3 CH3 H -OC{=O)O- CH=CHCH3
CH2CH3 CH3 CH3 -OC(=O)O- CH=CHCH3
CH2CH3 CH3 CI -OC(=O)O- CH=CHCH3
CH2CH3 CI CH3 -OC(=O)O- CH=CHCH3
CH2CH3 Cl Cl -OC(=O)O- CH=CHCH3
CH2CH3 H H -OC(=O)S- CH=CHCH3
CH2CH3 CH3 H -OC(=O)S- CH=CHCH3
CH2CH3 CH3 CH3 -OC(=O)S- CH=CHCH3
CH2CH3 CH3 Cl -OC(=O)S- CH=CHCH3
CH2CH3 Cl CH3 -OC(=O)S- CH=CHCH3
CH2CH3 Cl Cl -OC(=O)S- CH=CHCH3
CH2CH2CH3 H H -OC(=O)O- CH=CHCH3
CH2CH2CH3 CH3 H -OC{=O)O- CH=CHCH3
CH2CH2CH3 CH3 CH3 -OC(=O)O- CH=CHCH3
CH2CH2CH3 CH3 Cl -OC(=O)O- CH=CHCH3
CH2CH2CH3 CI CH3 -OC(=O)O- CH=CHCH3
CH2CH2CH3 CI CI -OC(=O)O- CH=CHCH3
CH2CH2CH3 H H -OC(=O)S- CH=CHCH3
CH2CH2CH3 CH3 H -OC(=O)S- CH=CHCH3
CH~CH2CH3 CH3 CH3 -OC(=O)S- CH=CHCH3
CH2CH2CH3 CH3 C1 -OC(=O)S- CH=CHCH3
CH2CH2CH3 Cl CH3 -OC(=O)S- CH=CHCH3
CH,CH2CH3 CI Cl -OC(=O)S- CH=CHCH3
CH3 H H -OC(=O)O- phenyl
CH3 CH3 H -OC(=O)O- phenyl
CH3 CH3 CH3 -OC(=O)O- phenyl
CH3 CH3 CI -OC(=O)O- phenyl
CH3 Cl CH3 -OC(=O)O- phenyl
CH3 CI CI -OC(=O)O- phenyl
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CH3 H H -OC{=O)S- phenyl
CH3 CH3 H -OC(=O)S- phenyl
CH3 CH3 CH3 -OC(=O)S- phenyl
CH3 CH3 Cl -OC(=O)S- phenyl
CH3 Cl CH3 -OC(=O)S- phenyl
CH3 Cl Cl -OC(=O)S- phenyl
CH2CH3 H H -OC(=O)O- phenyl
CH2CH3 CH3 H -OC(=O)O- phenyl
CH2CH3 CH3 CH3 -OC(=O)O- phenyl
CH2CH3 CH3 CI -OC(=O)O- phenyl
CH2CH3 CI CH3 -OC(=O)O- phenyl
CH~CH3 Cl Cl -OC(=O)O- phenyl
CH2CH3 H H -OC(=O)S- phenyl
CHZCH3 CH3 H -OC(=O)S- phenyl
CH2CH3 CH3 CH3 -OC(=O)S- phenyl
CH2CH3 CH3 CI -OC(=O)S- phenyl
CH2CH3 CI CH3 -OC{=O)S- phenyl
CH2CH3 C1 Cl -OC(=O)S- phenyl
CH2CH2CH3 H H -OC(=O)O- phenyl
CH2CH2CH3 CH3 H -OC(=O)O- phenyl
CH2CH2CH3 CH3 CH3 -OC(=O)O- phenyl
CH2CH2CH3 CH3 Cl -OC(=O)O- phenyl
CH2CH2CH3 C1 CH3 -OC(=O)O- phenyl
CH2CH2CH3 Cl Cl -OC(=O)O- phenyl
CH2CH2CH3 H H -OC(=O)S- phenyl
CH2CH2CH3 CH3 H -OC(=O)S- phenyl
CH2CHZCH3 CH3 CH3 -OC(=O)S- phenyl
CH2CH2CH3 CH3 Cl -OC(=O)S- phenyl
CH2CH2CH3 C1 CH3 -OC(=O)S- phenyl
CH2CH2CH3 CI Cl -OC(=O)S- phenyl
CH3 H H -OC(=O)O- 2-pyridinyl
CH3 CH3 H -OC(=O)O- 2-pyridinyl
CH3 CH3 CH3 -OC(=O)O- 2-pyridinyl
CH3 CH3 CI -OC(=O)O- 2-pyridinyl
CH3 C1 CH3 -OC(=O)O- 2-pyridinyl
CH3 C1 Cl -OC(=O)O- 2-pyridinyl
CH3 H H -OC(=O)S- 2-pyridinyl
CH3 CH3 H -OC(=O)S- 2-pyridinyl
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CH3 CH3 CH3 -OC(=O)S- 2-pyridinyl
CH3 CH3 Cl -OC(=O)S- 2-pyridinyl
CH3 C1 CH3 -OC(=O)S- 2-pyridinyl
CH3 C1 Cl -OC(=O)S- 2-pyridinyl
CH2CH3 H H -OC(=O)O- 2-pyridinyl
CH2CH3 CH3 H -OC(=O)O- 2-pyridinyl
CH2CH3 CH3 CH3 -OC(=O)O- 2-pyridinyl
CH2CH3 CH3 Cl -OC(=O)O- 2-pyridinyl
CH2CH3 C1 CH3 -OC(=O)O- 2-pyridinyl
CH2CH3 Cl Cl -OC(=O)O- 2-pyridinyl
CH2CH3 H H -OC(=O)S- 2-pyridinyl
CH2CH3 CH3 H -OC(=O)S- 2-pyridinyl
CH2CH3 CH3 CH3 -OC(=O)S- 2-pyridinyl
CH2CH3 CH3 Cl -OC(=O)S- 2-pyridinyl
CH2CH3 CI CH3 -OC(=O)S- 2-pyridinyl
CH2CH3 Cl CI -OC(=O)S- 2-pyridinyl
CH2CH2CH3 H H -OC(=O)O- 2-pyridinyl
CH2CH2CH3 CH3 H -OC(=O)O- 2-pyridinyl
CH2CH2CH3 CH3 CH3 -OC(=O)O- 2-pyridinyl
CH2CH2CH3 CH3 Cl -OC(=O)O- 2-pyridinyl
CH2CH2CH3 C1 CH3 -OC(=O)O- 2-pyridinyl
CH2CH2CH3 Cl Cl -OC(=O)O- 2-pyridinyl
CH2CH2CH3 H H -OC(=O)S- 2-pyridinyl
CH2CH2CH3 CH3 H -OC(=O)S- 2-pyridinyl
CH2CH2CH3 CH3 CH3 -OC(=O)S- 2-pyridinyl
CH2CH2CH3 CH3 Cl -OC(=O)S- 2-pyridinyl
CH~CH2CH3 Cl CH3 -OC(=O)S- 2-pyridinyl
CH2CH2CH3 Cl Cl -OC(=O)S- 2-pyridinyl
CH3 H H -OC(=O)O- 2-furanyl
CH3 CH3 H -OC(=O)O- 2-furanyl
CH3 CH3 CH3 -OC(=O)O- 2-furanyl
CH3 CH3 CI -OC(=O)O- 2-furanyl
CH3 Cl CH3 -OC(=O)O- 2-furanyl
CH3 CI Cl -OC(=O)O- 2-furanyl
CH3 H H -OC(=O)S- 2-furanyl
CH3 CH3 H -OC(=O)S- 2-furanyl
CH3 CH3 CH3 -OC(=O)S- 2-furanyl
CH3 CH3 Cl -OC(=O)S- 2-furanyl
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CH3 CI CH3 -OC(=O)S- 2-furanyl
CH3 Cl Cl -OC(=O)S- 2-furanyl
CH2CH3 H H -OC(=O)O- 2-furanyl
CH2CH3 CH3 H -OC(=O)O- 2-furanyl
CH2CH3 CH3 CH3 -OC(=O)O- 2-furanyl
CH2CH3 CH3 CI -OC(=O)O- 2-furanyl
CH2CH3 CI CH3 -OC(=O)O- 2-furanyl
CH2CH3 Cl C1 -OC(=O)O- 2-furanyl
CH2CH3 H H -OC(=O)S- 2-furanyl
CH2CH3 CH3 H -OC(=O)S- 2-furanyl
CH2CH3 CH3 CH3 -OC(=O)S- 2-furanyl
CH2CH3 CH3 CI -OC(=O)S- 2-furanyl
CH2CH3 Cl CH3 -OC(=O)S- 2-furanyl
CH2CH3 C1 Cl -OC(=O)S- 2-furanyl
CHZCH2CH3 H H -OC(=O)O- 2-furanyl
CH2CH2CH3 CH3 H -OC(=O)O- 2-furanyl
CH2CH2CH3 CH3 CH3 -OC(=O)O- 2-furanyl
CH2CH2CH3 CH3 Cl -OC(=O)O- 2-furanyl
CH2CH2CH3 C1 CH3 -OC(=O)O- 2-furanyl
CH2CH~CH3 Cl Cl -OC(=O)O- 2-furanyl
CH2CH2CH3 H H -OC(=O)S- 2-furanyl
CH2CH2CH3 CH3 H -OC(=O)S- 2-furanyl
CH2CH2CH3 CH3 CH3 -OC(=O)S- 2-furanyl
CH2CH2CH3 CH3 Cl -OC(=O)S- 2-furanyl
CH,CH2CH3 CI CH3 -OC{=O)S- 2-furanyl
CH2CHZCH3 Cl Cl -OC(=O)S- 2-furanyl
CH3 H H -OC(=O)O- 2-thienyl
CH3 CH3 H -OC(=O)O- 2-thienyl
CH3 CH3 CH3 -OC(=O)O- 2-thienyl
CH3 CH3 Cl -OC(=O)O- 2-thienyl
CH3 CI CH3 -OC(=O)O- 2-thienyl
CH3 C1 Cl -OC(=O)O- 2-thienyl
CH3 H H -OC(=O)S- 2-thienyl
CH3 CH3 H -OC(=O)S- 2-thienyl
CHg CH3 CH3 -OC(=O)S- 2-thienyl
CH3 CH3 CI -OC(=O)S- 2-thienyl
CH3 C1 CH3 -OC(=O)S- 2-thienyl
CH3 CI CI -OC(=O)S- 2-thienyl
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CH~CH3 H H -OC(=O)O- 2-thienyl
CH2CH3 CH3 H -OC(=O)O- 2-thienyl
CH2CH3 CH3 CH3 -OC(=O)O- 2-thienyl
CH2CH3 CH3 Cl -OC(=O)O- 2-thienyl
CH2CH3 Cl CH3 -OC(=O)O- 2-thienyl
CH2CH3 Cl Cl -OC(=O)O- 2-thienyl
CH2CH3 H H -OC(=O)S- 2-thienyl
CH2CH3 CH3 H -OC(=O)S- 2-thienyl
CH2CH3 CH3 CH3 -OC(=O)S- 2-thienyl
CH2CH3 CH3 Cl -OC(=O)S- 2-thienyl
CH2CH3 Cl CH3 -OC(=O)S- 2-thienyl
CH2CH3 C1 Cl -OC(=O)S- 2-thienyl
CH2CH2CH3 H H -OC(=O)O- 2-thienyl
CH2CH2CH3 CH3 H -OC(=O)O- 2-thienyl
CH2CH2CH3 CH3 CH3 -OC(=O)O- 2-thienyl
CH2CH2CH3 CH3 Cl -OC(=O)O- 2-thienyl
CH2CH2CH3 Cl CH3 -OC(=O)O- 2-thienyl
CH2CHzCH3 Cl Cl -OC(=O)O- 2-thienyl
CH2CH2CH3 H H -OC(=O)S- 2-thienyl
CH2CH2CH3 CH3 H -OC(=O)S- 2-thienyl
CH2CH2CH3 CH3 CH3 -OC(=O)S- 2-thienyl
CH~CH2CH3 CH3 Cl -OC(=O)S- 2-thienyl
CH2CH2CH3 Cl CH3 -OC(=O)S- 2-thienyl
CH2CH2CH3 Cl Cl -OC(=O)S- 2-thienyl
CH3 H H -OC(=O)- CH2CH2CH3
CH3 CH3 H -OC(=O)- CHZCH~CH3
CH3 CH3 CH3 -OC{=O)- CH2CH~CH3
CH3 CH3 Cl -OC(=O)- CH2CH2CH3
CH3 Cl CH3 -OC(=O)- CH~CH2CH3
CH3 CI Cl -OC(=O)- CH~CH2CH3
CH2CH3 H H -OC(=O)- CH2CH~CH3
CH2CH3 CH3 H -OC(=O)- CH2CH2CH3
CH2CH3 CH3 CH3 -OC(=O)- CH2CH2CH3
CH~CH3 CH3 Cl -OC(=O)- CH2CH2CH3
CH2CH3 Cl CH3 -OC(=O)- CH~CH~CH3
CH2CH3 Cl Cl -OC(=O)- CH2CH2CH3
CH2CH2CH3 H H -OC(=O)- CH~CH2CH3
CH2CH2CH3 CH3 H -OC(=O)- CH2CH~CH3
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CH2CH2CH3 CH3 CH3 -OC(=O)- CH2CH~CH3
CH2CH2CH3 CH3 Cl -OC(=O)- CH2CH2CH3
CH2CH2CH3 Cl CH3 -OC(=O)- CH2CH2CH3
CH2CH2CH3 C1 C1 -OC(=O)- CH2CH2CH3
CH3 H H -OC(=O)- cyclo-propyl
CH3 CH3 H -OC(=O)- cyclo-propyl
CH3 CH3 CH3 -OC(=O)- cyclo-propyl
CH3 CH3 Cl -OC(=O)- cyclo-propyl
CH3 CI CH3 -OC(=O)- cyclo-propyl
CH3 Cl Cl -OC(=O)- cvclo-propyl
CH2CH3 H H -OC(=O)- cyclo-propyl
CH2CH3 CH3 H -OC(=O)- cyclo-propyl
CH2CH3 CH3 CH3 -OC(=O)- cyclo-propyl
CH2CH3 CH3 Cl -OC(=O)- cyclo-propyl
CH2CH3 Cl CH3 -OC(=O)- cyclo-propyl
CH2CH3 C1 Cl -OC(=O)- cyclo-propyl
CH2CH2CH3 H H -OC(=O)- cyclo-propyl
CH2CH2CH3 CH3 H -OC(=O)- cyclo-propyl
CHZCHZCH3 CH3 CH3 -OC(=O)- cyclo-propyl
CH2CH2CH3 CH3 Cl -OC(=O)- cyclo-propyl
CH2CH2CH3 CI CH3 -OC(=O)- cyclo-propyl
CH2CH2CH3 CI Cl -OC(=O)- cyclo-propyl
CH3 H H -OC(=O)- CH=CH2
CH3 CH3 H -OC(=O}- CH=CH2
CH3 CH3 CH3 -OC(=O)- CH=CHI
CH3 CH3 Cl -OC(=O)- CH=CH2
CH3 Cl CH3 -OC(=O)- CH=CH2
CH3 Cl Cl -OC(=O)- CH=CHI
CH2CH3 H H -OC(=O)- CH=CH2
CH2CH3 CH3 H -OC(=O)- CH=CH2
CH2CH3 CH3 CH3 -OC(=O)- CH=CH2
CH2CH3 CH3 Cl -OC(=O)- CH=CH2
CH2CH3 CI CH3 -OC(=O)- CH=CH2
CH~CH3 Cl Cl -OC(=O)- CH=CH2
CH2CH2CH3 H H -OC(=O)- CH=CH2
CH~CH2CH3 CH3 H -OC(=O)- CH=CH2
CH~CH2CH3 CH3 CH3 -OC(=O)- CH=CH2
CH2CH2CH3 CH3 C1 -OC(=O)- CH=CH2
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CH2CH2CH3 C1 CH3 -OC(=O)- CH=CH2
CH2CH~CH3 CI CI -OC{=O)- CH=CH2
CH3 H H -OC(=O)- C(=CH2)CH3
CH3 CH3 H -OC(=O)- C(=CH2)CH3
CH3 CH3 CH3 -OC(=O)- C(=CH2)CH3
CH3 CH3 CI -OC(=O)- C{=CH2)CH3
CH3 Cl CH3 -OC(=O)- C{=CH2)CH3
CH3 Cl CI -OC(=O)- C(=CH2)CH3
CH2CH3 H H -OC(=O)- C(=CH2)CH3
CH2CH3 CH3 H -OC(=O)- C(=CH2)CH3
CH2CH3 CH3 CH3 -OC(=O)- C(=CH2)CH3
CH2CH3 CH3 CI -OC(=O)- C(=CH2)CH3
CH2CH3 Cl CH3 -OC(=O)- C(=CH2)CH3
CH2CH3 CI Cl -OC(=O}- C(=CH')CH3
CH2CH2CH3 H H -OC(=O)- C(=CH2)CH3
CH2CH2CH3 CH3 H -OC(=O)- C(=CH2)CH3
CH2CH2CH3 CH3 CH3 -OC(=O)- C(=CH2)CH3
CH2CHZCH3 CH3 CI -OC(=O)- C(=CHZ)CH3
CH2CH2CH3 CI CH3 -OC(=O)- C(=CH2)CH3
CH2CH~CH3 CI CI -OC(=O)- C(=CH2)CH3
CH3 H H -OC(=O)- CH2CH=CH2
CH3 CH3 H -OC(=O)- CH2CH=CH2
CH3 CH3 CH3 -OC(=O)- CH2CH=CH2
CH3 CH3 C1 -OC(=O)- CH2CH=CH2
CH3 CI CH3 -OC(=O)- CH2CH=CHI
CH3 Cl CI -OC(=O)- CH2CH=CH2
CH2CH3 H H -OC(=O)- CH2CH=CH2
CH2CH3 CH3 H -OC(=O)- CH2CH=CH2
CH2CH3 CH3 CH3 -OC(=O)- CH2CH=CHI
CH2CH3 CH3 CI -OC(=O)- CH2CH=CHZ
CH2CH3 CI CH3 -OC(=O)- CH2CH=CHI
CH2CH3 C1 CI -OC(=O)- CH2CH=CH2
CH2CH2CH3 H H -OC(=O)- CH2CH=CH2
CH2CH2CH3 CH3 H -OC(=O)- CH2CH=CH2
CH2CH2CH3 CH3 CH3 -OC(=O)- CH2CH=CH2
CH2CH2CH3 CH3 CI -OC(=O)- CH2CH=CH2
CH2CH2CH3 CI CH3 -OC(=O)- CH2CH=CH2
CH2CH~CH3 CI Cl -OC(=O)- CH2CH=CH2
,
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41
CH3 H H -OC(=O)- CH=CHCH3
CH3 CH3 H -OC(=O)- CH=CHCH3
CH3 CH3 CH3 -OC(=O)- CH=CHCH3
CH3 CH3 CI -OC(=O)- CH=CHCH3
CH3 Cl CH3 -OC(=O)- CH=CHCH3
CH3 CI Cl -OC(=O)- CH=CHCH3
CH2CH3 H H -OC(=O)- CH=CHCH3
CH2CH3 CH3 H -OC(=O)- CH=CHCH3
CH2CH3 CH3 CH3 -OC(=O)- CH=CHCH3
CH2CH3 CH3 Cl -OC(=O)- CH=CHCH3
CH2CH3 Cl CH3 -OC(=O)- CH=CHCH3
CH2CH3 Cl Cl -OC(=O)- CH=CHCH3
CHZCH2CH3 H H -OC(=O)- CH=CHCH3
CH2CH2CH3 CH3 H -OC(=O)- CH=CHCH3
CH2CH2CH3 CH3 CH3 -OC(=O)- CH=CHCH3
CH2CH2CH3 CH3 Cl -OC(=O)- CH=CHCH3
CH2CH2CH3 Cl CH3 -OC(=O)- CH=CHCH3
CH2CH2CH3 Cl Cl -OC(=O)- CH=CHCH3
CH3 H H -OC(=O)- phenyl
CH3 CH3 H -OC(=O)- phenyl
CH3 CH3 CH3 -OC(=O)- phenyl
CH3 CH3 Cl -OC(=O)- phenyl
CH3 Cl CH3 -OC(=O)- phenyl
CH3 Cl Cl -OC(=O)- phenyl
CH2CH3 H H -OC(=O)- phenyl
CH2CH3 CH3 H -OC{=O)- phenyl
CH2CH3 CH3 CH3 -OC(=O)- phenyl
CH2CH3 CH3 Cl -OC(=O)- phenyl
CH2CH3 Cl CH3 -OC(=O)- phenyl
CH2CH3 Cl Cl -OC(=O)- phenyl
CH2CH2CH3 H H -OC(=O)- phenyl
CH~CH2CH3 CH3 H -OC(=O)- phenyl
CH2CH2CH3 CH3 CH3 -OC(=O)- phenyl
CH2CH2CH3 CH3 Cl -OC(=O)- phenyl
CH2CHZCH3 Cl CH3 -OC(=O)- phenyl
CH2CH2CH3 Cl Cl -OC(=O)- phenyl
CH3 H H -OC(=O)- 2-pyridinyl
CH3 CH3 H -OC(=O)- 2-pyridinyl
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CH3 CH3 CH3 -OC(=O)- 2-pyridinyl
CH3 CH3 Cl -OC(=O)- 2-pyridinyl
CH3 Cl CH3 -OC(=O)- 2-pyridinyl
CH3 CI Cl -OC(=O)- 2-pyridinyl
CH2CH3 H H -OC(=O}- 2-pyridinyl
CH2CH3 CH3 H -OC(=O}- 2-pyridinyl
CH2CH3 CH3 CH3 -OC(=O)- 2-pyridinyl
CH2CH3 CH3 Cl -OC(=O)- 2-pyridinyl
CH2CH3 CI CH3 -OC(=O)- 2-pyridinyl
CH2CH3 Cl CI -OC(=O)- 2-pyridinyl
CH2CH2CH3 H H -OC(=O)- 2-pyridinyl
CH2CH2CH3 CH3 H -OC(=O)- 2-pyridinyl
CH2CHZCH3 CH3 CH3 -OC(=O)- 2-pyridinyl
CH~CH2CH3 CH3 Cl -OC(=O)- 2-pyridinyl
CH2CH2CH3 Cl CH3 -OC{=O)- 2-pyridinyl
CHZCH2CH3 Cl CI -OC(=O}- 2-pyridinyl
CH3 H H -OC(=O)- 2-furanyl
CH3 CH3 H -OC(=O)- 2-furanyl
CH3 CH3 CH3 -OC(=O)- 2-furanyl
CH3 CH3 Cl -OC(=O)- 2-furanyl
CH3 CI CH3 -OC(=O)- 2-furanyl
CH3 Cl C1 -OC(=O)- 2-furanyl
CH2CH3 H H -OC(=O)- 2-furanyl
CH2CH3 CH3 H -OC(=O)- 2-furanyl
CH2CHg CH3 CH3 -OC(=O)- 2-furanyl
CH2CH3 CH3 Cl -OC(=O)- 2-furanyl
CH2CH3 Cl CH3 -OC{=O)- 2-furanyl
CH2CH3 Cl CI -OC{=O}- 2-furanyl
CH2CH2CH3 H H -OC(=O)- 2-furanyl
CH2CH2CH3 CH3 H -OC(=O)- 2-furanyl
CH2CH2CH3 CH3 CH3 -OC(=O)- 2-furanyl
CH2CH2CH3 CH3 Cl -OC(=O)- 2-furanyl
CH2CH2CH3 CI CH3 -OC(=O)- 2-furanyl
CH2CH2CH3 CI Cl -OC(=O)- 2-furanyl
CH3 H H -OC(=O)- 2-thienyl
CH3 CH3 H -OC(=O)- 2-thienyl
CH3 CH3 CH3 -OC(=O)- 2-thienyl
CH3 CH3 CI -OC(=O)- 2-thienyl
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CH3 Cl CH3 -OC(=O)- 2-thienyl
CH3 CI CI -OC(=O)- 2-thienyl
CHzCH3 H H -OC(=O)- 2-thienyl
CH2CH3 CH3 H -OC(=O)- 2-thienyl
CH2CH3 CH3 CH3 -OC(=O)- 2-thienyl
CHZCH3 CH3 Cl -OC(=O)- 2-thienyl
CH2CH3 Cl CH3 -OC(=O)- 2-thienyl
CH2CH3 Cl Cl -OC(=O)- 2-thienyl
CH2CH~CH3 H H -OC(=O}- 2-thienyl
CH2CH2CH3 CH3 H -OC(=O)- 2-thienyl
CH2CH2CH3 CH3 CH3 -OC(=O)- 2-thienyl
CH2CH2CH3 CH3 Cl -OC(=O)- 2-thienyl
CH2CHZCH3 Cl CH3 -OC(=O}- 2-thienyl
CH2CH2CH3 Cl CI -OC(=O)- 2-thienyl
Table 3
H O Rz O
N \
RI/ I O s O
R3
R1 is CH2CH~, R2 and R3 are CH3
A- Q -A Q
-OC(=O)O- CH(CH3)2 -OC(=O}- CH(CH3)2
-OC(=O)S- CH(CH3)2 -OC(=O)- cyclo-butyl
-OC(=O)O- cyclo-butyl -OC(=O)- cyclo-pentyl
-OC(=O)S- cyclo-butyl -OC(=O)- cyclo-hexyl
-OC(=O)O- cyclo-pentyl -OC(=O}- 5-CH3-2-thienyl
-OC(=O)S- cyclo-pentyl -OC(=O}- S-Cl-2-thienyl
-OC(=O)O- cyclo-hexyl -OC(=O)- S-CH3-2-furanyl
-OC(=O)S- cyclo-hexyl -OC(=O)- S-Cl-2-furanyl
-OC(=O)O- S-CH3-2-thienyl -OC(=O)- 3-pyridinyl
-OC(=O)S- S-CH3-2-thienyl -OC(=O)- 4-pyridinyl
-OC(=O)O- S-Cl-2-thienyl -OC(=O)- 6-CH3-2-pyridinyl
-OC(=O)S- S-Cl-2-thienyl -OC(=O)- 6-Cl-2-pyridinyl
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44
-OC(=O}O- S-CH3-2-furanyl -OC(=O)- 2-CH3-phenyl
-OC(=O)S- S-CH3-2-furanyl -OC(=O)- 3-CH3-phenyl
-OC(=O)O- S-Cl-2-furanyl -OC(=O)- 4-CH3-phenyl
-OC(=O)S- S-CI-2-furanyl -OC(=O}- 2,6-diCH3-phenyl
-OC(=O)O- 3-pyridinyl -OC(=O)- 2-CI-phenyl
-OC(=O)S- 3-pyridinyl -OC(=O)- 3-Cl-phenyl
-OC(=O}O- 4-pyridinyl -OC(=O)- 4-CI-phenyl
-OC(=O)S- 4-pyridinyl -OC(=O)- 2-OCH3-phenyl
-OC(=O)O- 6-CH3-2-pyridinyl-OC(=O)- 3 OCH3-phenyl
-OC(=O)S- 6-CH3-2-pyridinyl-OC(=O}- 4-OCH3-phenyl
-OC(=O)O- 6-Cl-2-pyridinyl -OC(=O)- 2,6-diCl-phenyl
-OC(=O)S- 6-CI-2-pyridinyl -OC(=O)- 2,S-diCl-phenyl
-OC(=O)O- 2-CH3-phenyl -OC(=O)- 2,4-diCl-phenyl
-OC(=O)S- 2-CH3-phenyl
-OC(=O)O- 3-CH3-phenyl
-OC(=O)S- 3-CH3-phenyl
-OC(=O)O- 4-CH3-phenyl
-OC(=O)S- 4-CH3-phenyl
-OC(=O)O- 2,6-diCH3-phenyl
-OC(=O)S- 2,6-diCH3-phenyl
-OC(=O)O- 2-Cl-phenyl
-OC(=O)S- 2-CI-phenyl
-OC(=O)O- 3-Cl-phenyl
-OC{=O)S- 3-CI-phenyl
-OC(=O)O- 4-CI-phenyl
-OC(=O)S- 4-Cl-phenyl
-OC(=O)O- 2-OCH3-phenyl
-OC(=O)S- 2-OCH3-phenyl
-OC(=O)O- 3 OCH3-phenyl
-OC(=O)S- 3 OCH3-phenyl
-OC(=O)O- 4-OCH3-phenyl
-OC(=O)S- 4-OCH3-phenyl
-OC(=O)O- 2,6-diCl-phenyl
-OC(=O)S- 2,6-diCl-phenyl
-OC(=O)O- 2,S-diCl-phenyl
-OC(=O)S- 2,S-diCl-phenyl
-OC(=O)O-.2,4-diCl-phenyl
-OC(=O)S- 2,4-diCl-phenyl
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Table 4
R
R1 is CH2CH3, RZ and R3 are CH3
A SZ A Q
-OC(=O)O- CH(CH3)2 -OC(=O)- CH(CH3)2
-OC(=O)S- CH(CH3)2 -OC(=O)- cyclo-butyl
-OC(=O)O- cyclo-butyl -OC(=O)- cvclo-pentyl
-OC(=O)S- cyclo-butyl -OC(=O)- cyclo-hexyl
-OC(=O)O- cyclo-pentyl -OC(=O)- 5-CH3-2-thienyl
-OC(=O)S- cyclo-pentyl -OC(=O)- 5-Cl-2-thienyl
-OC(=O)O- cyclo-hexyl -OC(=O)- 5-CH3-2-furanyl
-OC(=O)S- cvclo-hexyl -OC(=O)- 5-Cl-2-furanyl
-OC(=O)O- S-CH3-2-thienyl -OC(=O)- 3-pyridinyl
-OC(=O)S- 5-CH3-2-thienyl -OC(=O)- 4-pyridinyl
-OC(=O)O- 5-C1-2-thienyl -OC(=O)- 6-CH3-2-pyridinyl
-OC(=O)S- 5-C1-2-thienyl -OC(=O)- 6-Cl-2-pyridinyl
-OC{=O)O- 5-CH3-2-furanyl -OC(=O)- 2-CH3-phenyl
-OC(=O)S- 5-CH3-2-furanyl -OC(=O)- 3-CH3-phenyl
-OC(=O)O- 5-CI-2-furanyl -OC(=O)- 4-CH3-phenyl
-OC(=O)S- 5-C1-2-furanyl -OC(=O)- 2,6-diCH~-phenyl
-OC(=O)O- 3-pyridinyl -OC(=O)- 2-C1-phenyl
-OC(=O)S- 3-pyridinyl -OC(=O)- 3-Cl-phenyl
-OC(=O)O- 4-pyridinyl -OC(=O)- 4-CI-phenyl
-OC(=O)S- 4-pyridinyl -OC(=O)- 2-OCH3-phenyl
-OC(=O)O- 6-CH3-2-pyridinyl-OC(=O)- 3 OCH3-phenyl
-OC(=O)S- 6-CH3-2-pyridinyl-OC(=O)- 4-OCH3-phenyl
-OC(=O)O- 6-Cl-2-pyridinyl-OC(=O}- 2,6-diCl-phenyl
-OC(=O)S- 6-C1-2-pyridinyl-OC(=O)- 2,5-diCl-phenyl
-OC(=O)O- 2-CH3-phenyl -OC(=O)- 2,4-diCl-phenyl
-OC(=O)S- 2-CH3-phenyl
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46
-OC(=O)O- 3-CH3-phenyl
-OC(=O)S- 3-CH3-phenyl
-OC(=O)O- 4-CH3-phenyl
-OC(=O)S- 4-CH3-phenyl
-OC(=O)O- 2,6-diCH3-phenyl
-OC(=O)S- 2,6-diCH3-phenyl
-OC(=O)O- 2-Cl-phenyl
-OC(=O)S- 2-Cl-phenyl
-OC(=O)O- 3-C1-phenyl
-OC(=O)S- 3-Cl-phenyl
-OC(=O)O- 4-Cl-phenyl
-OC(=O)S- 4-C1-phenyl
-OC(=O)O- 2-OCH3-phenyl
-OC(=O)S- 2-OCH3-phenyl
-OC(=O)O- 3 OCH3-phenyl
-OC(=O)S- 3 OCH3-phenyl
-OC(=O)O- 4-OCH~-phenyl
-OC(=O)S- 4-OCH3-phenyl
-OC(=O)O- 2,6-diCl-phenyl
-OC(=O)S- 2,6-diCl-phenyl
-OC(=O)O- 2,5-diCl-phenyl
-OC(=O)S- 2,5-diCl-phenyl
-OC(=O)O- 2,4-diCl-phenyl
-OC(=O)S- 2,4-diCl-phenyl
T.,1.1,~ C
H O R2 O
R l~ O ~ O v0
O~ R3
NR6R7
S
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47
Rt R2 R3 R~
R 7
CH2CH3 CH3 CH3 CH3 CH3
CH2CH3 CH3 CH3 CH~CH3 CHZCH3
CH2CH3 CH3 CH3 CH3 phenyl
CH2CH3 CH3 CH3 -CH2CH2CH2CH2-
CH2CH3 CH3 CH3 -CH~CH20CH~CH2-
Table 6
R
~6R7
R1 R2 R3 R6 R7
CH2CH3 CH3 CH3 CH3 CH3
CH2CH3 CH3 CH3 CH~CH3 CH2CH3
CH2CH3 CH3 CH3 CH3 phenyl
CH2CH3 CH3 CH3 -CH2CH~CH2CH2-
CH2CH3 CH3 CH3 -CH2CHZOCH~CH2-
Formulation/Utility
Compounds of this invention will generally be used as a formulation or
composition
with an agriculturally suitable carrier comprising at least one of a liquid
diluent, a solid
diluent or a surfactant. The formulation or composition ingredients are
selected to be
consistent with the physical properties of the active ingredient, mode of
application and
environmental factors such as soil type, moisture and temperature. Useful
formulations
include liquids such as solutions (including emulsifiable concentrates),
suspensions,
emulsions (including microemulsions and/or suspoemulsions) and the like which
optionally
can be thickened into gels. Useful formulations further include solids such as
dusts,
powders, granules, pellets, tablets, films, and the like which can be water-
dispersible
("wettable") or water-soluble. Active ingredient can be (micro)encapsulated
and further
formed into a suspension or solid formulation; alternatively the entire
formulation of active
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48
ingredient can be encapsulated (or "overcoated"). Encapsulation can control or
delay release
of the active ingredient. Sprayable formulations can be extended in suitable
media and used
at spray volumes from about one to several hundred liters per hectare. High-
strength
compositions are primarily used as intermediates for further formulation.
The formulations will typically contain effective amounts of active
ingredient, diluent
and surfactant within the following approximate ranges which add up to 100
percent by
weight.
Weight Percent
Active
In reg diem Diluent Surfactant
Water-Dispersible and Water-soluble 5-90 0-94 1-15
Granules, Tablets and Powders.
Suspensions, Emulsions, Solutions 5-50 40-95 0-15
(including Emulsifiable Concentrates)
Dusts 1-25 70-99 4-5
Granules and Pellets 0.01-99 5-99.99 0-15
High Strength Compositions 90-99 0-10 0-2
Typical solid diluents are described in Watkins, et al., Handbook
oflnsecticide Dust
Diluents and Carriers, 2nd Ed., Dorland Books, Caldwell, New Jersey. Typical
liquid
diluents are described in Marsden, Solvents Guide, 2nd Ed., Interscience, New
York, 1950.
McCutcheon 's Detergents and Emulsifiers Annual, Allured Publ. Corp.,
Ridgewood, New
Jersey, as well as Sisely and Wood, Encyclopedia of Surface Active Agents,
Chemical Publ.
Co., Inc., New York, 1964, list surfactants and recommended uses. All
formulations can
contain minor amounts of additives to reduce foam, caking, corrosion,
microbiological
growth and the like, or thickeners to increase viscosity.
Surfactants include, for example, polyethoxylated alcohols, polyethoxylated
alkylphenols, polyethoxylated sorbitan fatty acid esters, dialkyl
sulfosuccinates, alkyl
sulfates, alkylbenzene sulfonates, organosilicones, N,N dialkyltaurates,
lignin sulfonates,
naphthalene sulfonate formaldehyde condensates, polycarboxylates, and
polyoxyethylene/polyoxypropylene block copolymers. Solid diluents include, for
example,
clays such as bentonite, montmorillonite, attapulgite and kaolin, starch,
sugar, silica, talc,
diatomaceous earth, urea, calcium carbonate, sodium carbonate and bicarbonate,
and sodium
sulfate. Liquid diluents include, for example, water, N,N dimethylformamide,
dimethyl
sulfoxide, N alkylpyrrolidone, ethylene glycol, polypropylene glycol,
paraffins,
alkylbenzenes, alkylnaphthalenes, oils of olive, castor, linseed, tung,
sesame, corn, peanut,
cotton-seed, soybean, rape-seed and coconut, fatty acid esters, ketones such
as
cyclohexanone, 2-heptanone, isophorone and 4-hydroxy-4-methyl-2-pentanone, and
alcohols
such as methanol, cyclohexanol, decanol and tetrahydrofurfuryl alcohol.
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49
Solutions, including emulsifiable concentrates, can be prepared by simply
mixing the
ingredients. Dusts and powders can be prepared by blending and, usually,
grinding as in a
hammer mill or fluid-energy mill. Suspensions are usually prepared by wet-
milling; see, for
example, U.S. 3,060,084. Granules and pellets can be prepared by spraying the
active
material upon preformed granular carriers or by agglomeration techniques. See
Browning,
"Agglomeration", Chemical Engineering, December 4, 1967, pp 147-48, Perry's
Chemical
Engineer :s Handbook, 4th Ed., McGraw-Hill, New York, 1963, pages 8-57 and
following,
and WO 91/13546. Pellets can be prepared as described in U.S. 4,172,714.
Water-dispersible and water-soluble granules can be prepared as taught in U.S.
4,144,050,
U.S. 3,920,442 and DE 3,246,493. Tablets can be prepared as taught in U.S.
5,180,587, U.S.
5,232,701 and U.S. 5,208,030. Films can be prepared as taught in GB 2,095,558
and U.S.
3,299,566.
For further information regarding the art of formulation, see U.S. 3,235,361,
Col. 6,
line 16 through Col. 7, line 19 and Examples 10-41; U.S. 3,309,192, Col. 5,
line 43 through
I S Col. 7, line 62 and Examples 8, 12, 15, 39, 41, 52, 53, 58, 132, 138-140,
162-164, 166, 167
and 169-182; U.S. 2,891,855, Col. 3, line 66 through Col. 5, line 17 and
Examples I-4;
Klingman, Weed Control as a Science, John Wiley and Sons, Inc., New York,
1961,
pp 81-96; and Hance et al., Weed Control Handbook, 8th Ed., Blackwell
Scientific
Publications, Oxford, 1989.
In the following Examples, all percentages are by weight and all formulations
are
prepared in conventional ways. Compound numbers refer to compounds in Index
Table A.
Example A
High Strength Concentrate
Compound 14 9g,5%
silica aerogel 0.5%
synthetic amorphous fine silica 1.0%.
Example B
Wettable Powder
Compound 29 65.0%
dodecylphenol polyethylene glycol ether 2.0%
sodium ligninsulfonate 4.0%
sodium silicoaluminate 6.0%
montmorilIonite (calcined) 23.0%.
Example C
Granule
Compound 30 10.0%
attapulgite granules (low volatile matter,
0.71/0.30 mm; U.S.S. No. 25-50 sieves) 90.0%.
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Example D
Extruded Pellet
Compound 40 25.0%
anhydrous sodium sulfate 10.0%
5 crude calcium ligllinsulfonate 5.0%
sodium alkylnaphthalenesulfonate 1.0%
calcium/magnesium bentonite 59.0%.
Test results indicate that the compounds of the present invention are highly
active
preemergent and postemergent herbicides or plant growth regulants. Many of
them have
10 utility for broad-spectrum pre- and/or postemergence weed control in areas
where complete
control of all vegetation is desired such as around fuel storage tanks,
industrial storage areas,
parking lots, drive-in theaters, air fields, river banks, irrigation and other
waterways, around
billboards and highway and railroad structures. Some of the compounds are
useful for the
control of selected grass and broadleaf weeds with tolerance to important
agronomic crops
15 which include but are not limited to alfalfa, barley, cotton, wheat, rape,
sugar beets, corn
(maize), sorghum, soybeans, rice, oats, peanuts, vegetables, tomato, potato,
perennial
plantation crops including coffee, cocoa, oil palm, rubber, sugarcane; citrus,
grapes, fruit
trees, nut trees, banana, plantain, pineapple, hops, tea and forests such as
eucalyptus and
conifers (e.g., loblolly pine), and turf species (e.g., Kentucky bluegrass,
St. Augustine grass,
20 Kentucky fescue and Bermuda grass). Those skilled in the art will
appreciate that not all
compounds are equally effective against all weeds. Alternatively, the subject
compounds are
useful to modify plant growth.
A herbicidally effective amount of the compounds of this invention is
determined by a
number of factors. These factors include: formulation selected, method of
application,
25 amount and type of vegetation present, growing conditions, etc. In general,
a herbicidalIy
effective amount of compounds of this invention is 0.001 to 20 kg/ha with a
preferred range
of 0.004 to 1.0 kg/ha. One skilled in the art can easily determine the
herbicidally effective
amount necessary for the desired level of weed control.
Compounds of this invention can be used alone or in combination with other
30 commercial herbicides, insecticides or fungicides. Compounds of this
invention can also be
used in combination with commercial herbicide safeners such as benoxacor,
dichlormid and
furilazole to increase safety to certain crops. A mixture of one or more of
the following
herbicides with a compound of this invention may be particularly useful for
weed control:
acetochlor, acifluorfen and its sodium salt, aclonifen, acrolein (2-propenal),
alachlor,
35 ametryn, amidosulfuron, amitrole, ammonium sulfamate, anilofos, asulam,
atrazine,
azafenidin, azimsuIfuron, benazolin, benazolin-ethyl, benfluralin,
benfuresate,
bensulfuron-methyl, bensulide, bentazone, bifenox, bispyribac and its sodium
salt, bromacil,
bromoxynil, bromoxynil octanoate, butachlor, butralin, butroxydim (ICIA0500},
butylate,
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51
caloxydim (BAS 620H), carfentrazone-ethyl, chlomethoxyfen, chloramben,
chlorbromuron,
chloridazon, chlorimuron-ethyl, chlornitrofen, chlorotoluron, chlorpropham,
chlorsulfuron,
chlorthal-dimethyl, cinmethylin, cinosulfuron, clethodim, clomazone,
ciopyralid,
clopyralid-olamine, cyanazine, cycloate, cyclosulfamuron, 2,4-D and its
butotyl, butyl,
isoctyl and isopropyl esters and its dimethylammonium, diolamine and trolamine
salts,
daimuron, dalapon, dalapon-sodium, dazomet, 2,4-DB and its dimethylammonium,
potassium and sodium salts, desmedipham, desmetryn, dicamba and its
diglycolammonium,
dimethylammonium, potassium and sodium salts, dichlobenil, dichlorprop,
diclofop-methyl,
2-[4,S-dihydro-4-methyl-4-(I-methylethyl)-5-oxo-1H imidazol-2-yl]-5-methyl-3-
pyridinecarboxylic acid (AC 263,222), difenzoquat metilsulfate, diflufenican,
dimepiperate,
dimethenamid, dimethylarsinic acid and its sodium salt, dinitramine,
diphenamid, diquat
dibrornide, dithiopyr, diuron, DNOC, endothal, EPTC, esprocarb, ethalfluralin,
ethametsulfuron-methyl, ethofumesate, ethoxysulfuron, fenoxaprop-ethyl,
fenoxaprop-P-ethyl, fenuron, fenuron-TCA, flamprop-methyl, flamprop-M-
isopropyl,
flamprop-M-methyl, flazasulfuron, fluazifop-butyl, fluazifop-P-butyl,
fluchloralin,
flumetsulam, flumiclorac-pentyl, flumioxazin, fluometuron, fluoroglycofen-
ethyl, flupoxam,
flupyrsulfuron-methyl and its sodium salt, fluridone, flurochloridone,
fluroxypyr,
fluthiacet-methyl, fomesafen, fosamine-ammonium, glufosinate, glufosinate-
ammonium,
glyphosate, glyphosate-isopropylammonium, glyphosate-sesquisodium,
glyphosate-trimesium, halosulfuron-methyl, haloxyfop-etotyl, haloxyfop-methyl,
hexazinone, imazamethabenz-methyl, imazamox, imazapyr, imazaquin,
imazaquin-ammonium, imazethapyr, imazethapyr-ammonium, imazosulfuron, ioxynil,
ioxynil octanoate, ioxynil-sodium, isoproturon, isouron, isoxaben,
isoxaflutole, lactofen,
lenacil, linuron, malefic hydrazide, MCPA and its dimethylammonium, potassium
and
sodium salts, MCPA-isoctyl, mecoprop, mecoprop-P, mefenacet, mefluidide, metam-
sodium,
methabenzthiazuron, methylarsonic acid and its calcium, monoammonium,
monosodium and
disodium salts, methyl [[[1-[S-[2-chloro-4-(trifluoromethyl)phenoxy]-2-
nitrophenyl]-2-
methoxyethylidene]amino]oxy]acetate (AKH-7088), methyl 5-[[[[(4,6-dimethyl-2-
pyrimidinyl)amino]carbonyl]amino] sulfonyl]-1-(2-pyridinyl)-1 H-pyrazole-4-
carboxylate
(NC-330), metobenzuron, metolachlor, metosulam, metoxuron, metribuzin,
metsulfuron-methyl, molinate, monolinuron, napropamide, naptalam, neburon,
nicosulfuron,
norflurazon, oryzalin, oxadiazon, oxasulfuron, oxyfluorfen, paraquat
dichloride, pebulate,
pendimethalin, pentoxazone (KPP-314), perfluidone, phenmedipham, picloram,
picloram-potassium, pretilachlor, primisulfuron-methyl, prometon, prometryn,
propachlor,
propanil, propaquizafop, propazine, propham, propyzamide, prosulfuron,
pyrazolynate,
pyrazosulfuron-ethyl, pyridate, pyriminobac-methyl, pyrithiobac, pyrithiobac-
sodium,
quinclorac, quizalofop-ethyl, quizalofop-P-ethyl, quizalofop-P-tefuryl,
rimsulfuron,
sethoxydim, siduron, simazine, sulcotrione (ICIA0051 ), sulfentrazone,
sulfometuron-methyl,
CA 02281904 1999-08-20
WO 98/49159 PCT/US98/07978
52
TCA, TCA-sodium, tebuthiuron, terbacil, terbuthylazine, terbutryn,
thenylchlor, thiafluamide
(BAY 11390), thifensulfuron-methyl, thiobencarb, tralkoxydim, tri-allate,
triasulfuron,
triaziflam, tribenuron-methyl, triclopyr, triclopyr-butotyl, triclopyr-
triethylammonium,
tridiphane, trifluralin, triflusulfuron-methyl, and vernolate.
In certain instances, combinations with other herbicides having a similar
spectrum of
control but a different mode of action will be particularly advantageous for
preventing the
development of resistant weeds.
The following Tests demonstrate the control efficacy of the compounds of this
invention against specific weeds. The weed control afforded by the compounds
is not
limited, however, to these species. See Index Tables A and B for compound
descriptions.
The following abbreviations are used in the Index Tables which follow: Ph =
phenyl. The
abbreviation "dec" indicates that the compound appeared to decompose on
melting. The
abbreviation "Ex." stands for "Example" and is followed by a number indicating
in which
example the compound is prepared.
INDEX TABLE
H O CH3 R4 RS
R1/ ~ ~3 O S O
Q
R1 is CH2CH3
Cmnd A Q R4 RS mt~ (C)
I OC(=O) C(=CH2)CH3 C=O 63 (dec)
2 OC(=O) Ph C=O 70 (dec)
3 OC(=O) CH(CH3)2 C=O 62-63 (dec)
4 OC(=O) 2,5-diCl-6-OCH3Ph C=O oil
5 OC(=O) 4-CH3Ph C=O 81 (dec)
6 OC(=O) cyclopropyl C=O 77 (dec)
7 OC(=O) 3,6-diCl-pyridin-2-ylC=O 21 S-217
8 OC(=O) furan-2-yl C=O 70 (dec)
9 OC(=O) 2-CH3Ph C=O 201-203
10 OC(=O) 2-FPh C=O 153-155
I 1 OC(=O) 4-FPh C=O I 58-160
12 OC(=O) 4-BrPh C=O 98 (dec)
13 OC(=O) C(=CH2)CH3 -OCH2CH20- 175-177
(dcc)
14 OC(=O) Ph -OCH2CH20- 179-180
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WO 98/49159 PCT/US98/07978
53
15 OC(=O) CH(CH3)2 -OCH2CH20- 73 (dec)
16 OC(=O) 2,5-diCl-6-OCH3Ph -OCI-I2CH20- 198-200
17 OC(=O) cyclopropyl -OCH2CH20- 215-217
18 OC(=O) 3,6-diCl-pyridin-2-yl-OCH2CH20- 228-230
19 OC(=O) furan-2-yl -OCH2CH20- 201-203
20 OC(=O) 4-FPh -OCH2CH20- 237-239
21 OC(=O) C(CH3)3 -OCH2CH20- >200
23 OC(=O)O CH(CH3)2 C=O 58-60 (dec)
24 OC(=O)O CH2CH3 C=O 58 (dec}
25 OC(=O)O CH2CH=CH2 C=O oil*
26 OC(=O)O CH3 C=O 135-137
27 OC(=O)O Ph C=O 68 (dec)
28 OC(=O)O CH2CH2CH3 C=O 68 (dec)
29 (Ex.OC(=O)O CH(CH3)2 -OCH2CH20- 168-170
1)
30 (Ex.OC(=O)O CH2CH3 -OCH2CH20- 201-203
2)
31 OC(=O)O CH3 -OCH2CH20- 191-193
32 OC(=O)O CH2CH=CH2 -OCH2CH20- 72-74
33 OC(=O)O CH2CH2CH3 -OCH2CH20- 74 (dec)
34 OC(=O)O Ph -OCH2CH20- 215
35 OC(=O)O CH2CH(CH3)2 -OCH2CH20- 65-67 (dec)
36 OC(=O)O CH2CH2CH2CH3 -OCH2CH20- 62 (dec)
37 OC(=O)O CH2CI-I20CH3 -OCH2CH20- 113 (dec)
38 OC(=O)O CH2CH2CH2CH2CH3 -OCH2CH20- 58 {dec)
39 OC(=O)O (CH2)SCH3 -OCH2CH20- 48 (dec)
40 OC{=O)O CH2Ph -OCH2CH20- 171
41 OC(=O)O (CH2)7CH3 -OCH2CH20- 47 (dec)
42 OC(=O}O CH2C1 -OCH2CH20- 61-62 (dec)
43 OC(=O)O CH2CH2CH2CH2Cl -OCH2CH20- 48-50 (dec)
44 OC(=O)O CH2CH2Cl -OCH2CH20- 169-171
(dec)
45 OC(=O)O CI-i2CH2Br -OCH2CH20- 170-172
(dec)
46 OC(=O)O 4-BrPh -OCH2CH20- 85-98
47 OC(=O)O 4-CIPh -OCH2CH20- 78-90
48 OC(=O)O 4-OCH3Ph -OCH2CH20- 160-163
49 OC(=O)O 4-CH3Ph -OCH2CH20- 176-182
50 OC(=O)N(CH3)2 -OCH2CH20- 239-241
51 OC(=O)N(CH2CH3)2 -OCH2CH20- oil
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WO 98/49159 PCT/US98/07978
54
52 -OCH2CH20- 177-179
OC(=O)N
53 OC(=O)N(CH3)Ph -OCH2CH20- 98-102
54 OC(=O)N(CH(CH3)2)2 -OCH2CH20- 107-112
55 ~ -OCH2CH20- semi-solid
OC(=O)N\
~
/
56 C -OCH2CH20- 173-174
H2CH3
OC(=O)S
57 OC{=O)S CH3 -OCH2CH20- 172-175
58 OC(=O)S Ph -OCH2CH20- 170-171
59 OC(=O)S 4-CIPh -OCH2CH20- i76-177
*See Table B for 1H NMR
Index data.
R1 is CH3
Cmpd A Q R4 R5 mp (°C)
60 OC(=O)O CH2CH3 -OCH2CH20- 155-157
61 OC(=O)O CH2CH2CH3 -OCH2CH20- 160-162
62 OC(=O)O CH2Ph -OCH2CH20- 85-87
INDEX TABLE B
Cmpd No. 1H NMR Data (CDC1~ solution unless indicated otherwise)a
4 8 1.5 (t, 3H), 2.48 {s, 3H), 2.76 (s, 3Ii), 3.34 (m, 2H), 3.74 (m, 2H), 4.05
(s, 3H), 4.21 (q, 2H), 7.24 (d, 1H), 7.43 (s, 1H), 7.51 (m, 2H).
21 8 1.22 (s, 9H), 1.31 (t, 3II), 2.17 (s, 3H), 2.45 (m, 2H), 2.63 (s, 3H),
3.39
(m, 2H), 3.88 (q, 2tI), 3.9-4.19 (m, 4H), 7.08 (s, 1H), 7.44 (s, 1H).
25 8 1.46 (t, 3H), 2.43 (s, 3H), 2.76 (s, 3H), 3.35 (m, 2H), 3.75 (m, 2H),
4.10
(m, 2H), 4.78 (d, 2H), 5.4 (m, 2H), 6.0 (m, 1H), 7.37 (s, 1H), 7.51 (s, 1H).
51 8 1.172 (t, 3H), 1.196 (t, 3H), 1.453 (t, 3H), 2.279 (s, 3H), 2.55 (m, 2H),
2.733 (s, 3H), 3.2 (q, 2H), 3.3 (q, 2H), 3.5 (m, 2H), 4.0 (q, 2II), 4.15 (m,
2H), 4.25 (m, 2H), 7.2 (s, 1H), 7.7 (s, IH).
55 8 1.460 (t, 3H), 2.280 (s, 3H), 2.6 (m, 2H), 2.741 (s, 3H), 3.5 (m, 6H),
3.75 (m, 4H), 4.0 (q, 2H), 4.2 (m, 2H), 4.3 (m, 2H), 7.191 (s, 1 H0, 7.65 (s,
1 H).
a 1H NMR data are in ppm downfield from tetramethylsilane. Couplings are
designated by
(s)-singlet, (d)-doublet, (t)-triplet, (q)-quartet, (m)-multiplet, (dd)-
doublet of doublets,
(dt)-doublet of triplets, (br s)-broad singlet.
CA 02281904 1999-08-20
WO 98/49159 PCT/US98/07978
BIOLOGICAL EXAMPLES OF THE INVENTION
Test A
Seeds of broadleaf signalgrass (Brachiaria decumbens), barley (Hordeum
vulgare),
5 barnyardgrass (Echinochloa crux-galli), bedstraw (Galium aparine),
blackgrass (Alopecurus
myosuroides), chickweed (Stellaria media), cocklebur (Xanthium strumarium),
corn (Zea
mays), cotton (Gossypium hirsutum), crabgrass (Digitaria sanguinalis), downy
brome
(Bromus tectorum), giant foxtail (Setaria faberii), lambsquarters (Chenopodium
album),
morningglory (Ipomoea hederacea), rape (Brassica napus), redroot pigweed
(Amaranthus
10 retroJlexa~s), rice (Oryza sativa), sorghum (Sorghum bicolor), soybean
(Glycine max), sugar
beet (Beta vulgaris), velvetleaf (Abutilon theophrasti), wheat (Triticum
aestivum), wild
buckwheat (Polygonum convolvulus), wild oat {Avena fatua) and purple nutsedge
(Cyperus
rotundas) tubers were planted and treated preemergence with test chemicals
formulated in a
non-phytotoxic solvent mixture which included a surfactant. A sprayed paddy
pot was
15 treated with some designated compounds. This paddy contained rice,
barnyardgrass,
smallflowered flatsedge (Cyperus difformis) and duck salad (Heteranthera
limosa) as the
target species and was sprayed alongside the other crop and weed species.
At the same time, these crop and weed species were also treated with
postemergence
applications of test chemicals formulated in the same manner. Plants ranged in
height from 2
20 to 18 cm (1- to 4-leaf stage) for postemergence treatments. Treated plants
and controls were
maintained in a greenhouse for twelve to sixteen days, after which all species
were compared
to controls and visually evaluated. Plant response ratings, summarized in
Table A, are based
on a scale of 0 to 10 where 0 is no effect and 10 is complete control. A dash
(-) response
means no test result.
CA 02281904 1999-08-20
WO 98/49159 PCT/US98/07978
56
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CA 02281904 1999-08-20
WO 98/49159 PCT/US98/07978
57
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CA 02281904 1999-08-20
WO 98/49159 PCT/US98/07978
58
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CA 02281904 1999-08-20
WO 98/49159 PCT/US98/07978
59
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CA 02281904 1999-08-20
WO 98/49159 PCT/US98/07978
61
Table A COMPOUND Table A COMPOUND
Rate 50 g/ha25 2630 31 32 Rate 10 g/ha 2526 30 31
32
SPRAYED PADDY SPRAYED PADDY
Barnyardgrass10 1010 9 10 Barnyardgrass 1010 10 7
10
Ducksalad 6 5 6 3 6 Ducksalad 4 4 2 0
4
Rice 10 9 10 10 10 Rice 8 6 9 5
9
S. flatsedge7 9 6 6 8 S. flatsedge 4 6 2 4
5
Test B
Seeds of broadleaf signalgrass (Brachiaria decumbens), bedstraw (Galium
aparine),
bIackgrass (Alopecurus myosuroides), cocklebur (Xanthium strumarium), corn
(Zea mays),
crabgrass (Digitar-ia sanguinalis), giant foxtail (Setaria.faberii),
morningglory (Ipomoea
hederacea), rape (Brassica napus), pigweed (Amaranthus retroJlexus), soybean
(Glvcine
max), sugar beet (Beta vulgaris), velvetleaf (Abutilon theophrasti), wheat (Ti-
iticum
aestivum), wild oat (Avena fatua) and purple nutsedge (Cyperus rotundus)
tubers were
planted and treated preemergence with test chemicals formulated in a non-
phytotoxic solvent
mixture which included a surfactant.
At the same time, these crop and weed species were also treated with
postemergence
applications of test chemicals formulated in the same manner. Plants ranged in
height from 2
to 18 cm ( 1- to 4-leaf stage) for postemergence treatments. Plant species in
the flood test
1 S consisted of rice (Oryza sativa), smallflower flatsedge (Cyperus
difformis), duck salad
(Heteranthera limosa) and barnyardgrass (Echinochloa crus-galli) grown to the
2-leaf stage
for testing. Treated plants and controls were maintained in a greenhouse for
twelve to
sixteen days, after which all species were compared to controls and visually
evaluated. Plant
response ratings, summarized in Table B, are based on a scale of 0 to 10 where
0 is no effect
and 10 is complete control. A dash (-) response means no test result.
Table B COMPOUND
Rate 62 g/ha 17 19 23 25 29 60 61 62
Postemergence
B. signalgrass 10 9 5 6 9 3 4 -
Barnyardgrass 9 5 9 0 9 0 2 0
Bedstraw 10 9 9 9 9 9 2 -
Blackgrass 6 5 3 3 5 1 3
Cocklebur 10 10 9 9 10 10 9
Corn 7 6 1 0 6 0 6
Crabgrass 10 10 9 9 10 9 9
CA 02281904 1999-08-20
WO 98/49159 PCTNS98/07978
b2
Ducksalad 2 1 1 0 2 0 0 0
Giant foxtail 10 10 9 9 10 5 9 -
Morningglory 10 10 8 5 10 9 9 -
Nutsedge 8 3 0 0 8 0 - -
Rape 9 10 8 9 9 10 9 -
Redroot pigweed 10 9 9 9 10 9 9 -
Rice 6 3 7 2 4 0 0 0
S. Flatsedge 5 3 5 3 4 0 4 0
Soybean 10 10 9 10 10 9 9 -
Sugarbeets 10 10 9 9 10 10 IO
Velvetleaf 10 10 9 9 10 10 20 -
Wheat 7 6 3 3 5 1 1
Wild oats 9 10 1 1 7 2 4 -
Table B COMPOUND
Rate 62 g/ha 17 19 23 25 29 60 61
Preemergence
B. signalgrass 8 8 0 - 8 0 0
Bedstraw 7 5 2 0 7 0 -
Blackgrass 1 0 0 0 0 0 0
Cocklebur 0 0 0 0 0 0 0
Corn 0 0 0 0 0 0 1
Crabgrass 9 8 6 4 9 2 2
Giant foxtail 8 8 7 5 9 1 1
Morningglory 0 0 0 1 6 0 1
Nutsedge 0 0 0 0 0 - 0
Rape 0 6 0 1 0 0 0
Redroot pigweed 9 9 9 0 9 0 4
Soybean 0 0 0 0 0 0 0
Sugarbeets 9 10 8 9 10 3 0
Velvetleaf 10 9 3 2 10 3 9
Wheat 0 0 0 0 0 0 0
Wild oats 0 0 0 0 0 0 0
CA 02281904 1999-08-20
WO 98/49159 PCT/US98/07978
63
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WO 98/49159 PCTNS98/07978
66
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WO 98/49159 PCT/US98/07978
67
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68
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Test C
Seeds of barnyardgrass (Echinochloa crus-galli), bindweed (Concolculus
arvensis),
black nightshade (Solanum ptycanthum dunal), cassia (Cassia obtusifolia),
cocklebur
S (Xanthium strumarium), common ragweed (Ambrosia artemisiifolia), varieties
of corn {Zea
mays designated 'Corn 2' and 'Corn S'), cotton (Gossypium hirsutam), crabgrass
(Digitaria
spp.), fall panicum (Panicum dichotomiJlorum), giant foxtail (Setaria
faberii), green foxtail
(Setaria viridis), jimsonweed (Datura stramonium), johnsongrass (Sor~~hum
halepense),
lambsquarter (Chenopodium album), morningglory (Ipomoea spp.), pigweed
(Amaranthus
retroJlexus), prickly sida (Silo spinosa), shattercane (Sorghum
vulgar°e), signalgrass
(Brachiaria platyphylla), smartweed (Polygonum pensylvanicum), varieties of
soybean
(Glycine max designated 'Soybean 1' and 'Soybean 2'), sunflower (Helianthus
annuus),
velvetleaf (Abutilon theophrasti), wild proso (Pancium miliaceum), woolly
cupgrass
(Eriochloa villosa), yellow foxtail (Setarla lutescens) and purple nutsedge
(Cyperus
1 S rotundus) tubers were planted into a clay loam soil. These crops and weeds
were grown in
the greenhouse until the plants ranged in height from two to eighteen cm (one-
to four-leaf
stage), then treated postemergence with the test chemicals formulated in a non-
phytotoxic
solvent mixture which included a surfactant. Pots receiving preemergence
treatments were
planted immediatley prior to test chemical application. Pots treated in this
fashion were
placed in the greenhouse and maintained according to routine greenhouse
procedures.
Treated plants and untreated controls were maintained in the greenhouse
approximately 14-21 days after application of the test compound. Visual
evaluations of
plant injury responses were then recorded. Plant response ratings, sununarized
in Table C,
are reported on a 0 to 100 scale where 0 is no effect and 100 is complete
control.
2S
Table C COMPOUND
Rate 70 g/ha 1 2 3 6 7 8 13 14 15 24 29 30
POSTEMERGENCE
Barnyardgrass 100 85 100 100 80 85 100 100 100 85 100
Bindweed 85 85 85 90 70 80 85 100 100 80 100 80
Blk nightshade 80 100 100 100 - 100 85 85 95 70 100 90
Cassia 25 30 60 75 50 30 50 20 20 35 50 5
Cocklebur 100 100 100 100 80 100 100 100 100 100 100 95
Corn 2 60 75 70 60 0 65 40 0 0 90 0 20
Corn 5 10 0 0 0 0 10 35 5 10 45 0 10
Cotton 100 100 100 100 80 80 100 100 100 85 100 95
Crabgrass 90 80 90 100 100 100 100 100 100 100 100 100
Fall panicum 100 100 100 100 100 100 100 100 100 100 100 100
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Giant foxtail 100 95 100 100 100 100 100 100 100 100 100 100
Green foxtail 100 100 100 100 100 100 200 100 100 100 100 100
Jimsonweed 100 100 100 100 100 100 100 100 100 100 100 100
Johnsongrass - - - - 40 100 100 100 100 100 100 95
Lambsquarters 100 100 100 100 100 100 100 100 100 100 100 95
Morningglory 100 100 100 100 100 100 100 100 100 100 100 90
Nutsedge 0 0 0 90 25 15 20 55 30 20 30 35
Pigweed 100 100 100 100 40 60 100 100 100 100 100 85
Prickly sida 20 55 70 75 25 70 100 100 100 85 85 100
Ragweed 85 100 100 100 80 60 100 100 100 65 100 95
Shattercane 85 70 70 100 20 10 100 100 100 100 100 95
Signalgrass 100 100 30 100 70 90 100 85 80 100 70 90
Smartweed - - - - - - - - - - - -
Soybean 1 100 100 100 100 100 100 100 100 100 85 100 90
Soybean 2 100 100 100 100 100 75 100 100 100 85 100 95
Sunflower 100 100 100 100 100 100 100 100 100 100 100 95
Velvetleaf 100 100 100 100 100 100 100 100 100 100 100 100
V~ild proso 100 100 100 100 100 100 - 100 - 100 100 100
Woolly cupgrass 65 85 75 85 65 85 100 100 100 85 100 100
Yellow foxtail 100 100 100 100 100 100 100 100 100 100 100 100
Table C COMPOUND
Rate 35 g/ha 1 2 3 6 7 8 13 14 15 24 29 30
POSTEMERGENCE
Barnyardgrass 100 85 100 100 80 80 100 100 100 80 100 100
Bindweed 80 85 75 70 60 70 85 100 75 75 80 70
Blk nightshade 80 80 85 75 50 50 80 80 80 50 80 90
Cassia 25 30 60 60 25 20 20 20 20 25 50
Cocklebur 100 100 90 85 70 100 100 100 100 80 100 90
Corn 2 50 50 25 25 0 0 15 0 0 15 0 5
Corn 5 50 25 20 - 0 10 15 5 5 10 0 0
Cotton 100 100 100 100 75 70 100 100 100 50 100 90
Crabgrass 85 80 85 100 100 80 85 100 100 85 100 95
Fall panicum 100 100 100 100 100 100 100 100 100 100 100 100
Giant foxtail 90 90 100 100 100 100 100 100 100 80 100 100
Green foxtail 100 100 100 100 100 100 100 100 100 75 100 100
Jimsonweed 100 100 100 100 100 100 100 I00 100 100 100 100
Johnsongrass - - - - 25 80 100 100 100 80 30 90
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Lambsquarters100 100100100 100100100 100100100 10090
Morningglory 80 75 10080 70 70 100 100100100 10090
Nutsedge 0 0 0 0 15 15 15 30 25 15 25 30
Pigweed 80 85 80 90 20 60 100 10010050 10050
Prickly sida 20 55 35 40 10 25 100 85 85 10 80 100
Ragweed 70 70 85 100 80 60 100 10010060 10095
Shattercane 45 70 75 100 45 75 100 75 10070 10090
Signalgrass 0 40 20 100 55 85 100 45 80 55 70 90
Smartweed - - - - - - - - - - - -
Soybean 1 100 100100100 100100100 10085 65 10090
Soybean 2 100 70 100100 10075 100 10010060 10080
Sunflower 100 100100100 100100100 10010080 10090
Velvetleaf 100 100100100 100100100 10010080 100100
Wild proso 100 100100100 100100- 100- 100 100100
Woolly cupgrass55 70 70 85 65 75 75 85 85 75 85 100
Yellow foxtail100 10090 100 80 100100 10010080 95 100
Table C COMPOUND
Rate 17 g/ha 1 2 3 6 7 8 13 14 15 24 29 30
POSTEMERGENCE
Barnyardgrass100 85 90 100 80 - 100 10080 80 85 100
Bindweed 60 70 65 70 50 60 85 75 75 40 75 70
Blk nightshade80 80 80 80 50 40 80 80 80 50 80 85
Cassia 15 25 25 25 - - 20 20 20 - 20 0
Cocklebur 75 75 85 85 50 100100 10090 70 10090
Corn 2 0 0 0 0 0 0 5 0 0 10 0 0
Corn 5 3 0 0 0 0 5 5 0 0 0 0 0
0
Cotton 100 80 75 100 50 70 100 10010040 10080
Crabgrass 70 55 75 80 50 85 80 85 80 50 80 90
Fall panicum 90 10060 80 100100100 10085 100 10090
Giant foxtail85 90 100100 85 100100 10080 80 100100
Green foxtail100 100100100 60 85 100 10010070 10095
Jimsonweed 100 100100100 80 100100 100100100 100100
Johnsongrass - - - - 25 15 80 10025 30 15 70
Lambsquarters100 100100100 85 100100 100100100 10070
Morningglory 70 75 80 70 60 65 100 90 80 100 10080
Nutsedge 0 0 0 0 15 10 10 15 15 15 15 10
Pigweed 85 80 65 80 20 50 200 85 10020 10050
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Prickly sida 15 20 25 40 10 15 75 80 10010 80 70
Ragweed 70 80 - 85 50 40 100100 10040 10090
Shattercane 15 55 30 30 45 50 45 65 60 65 65 50
Signalgrass 20 20 15 90 55 85 10040 35 15 BO 50
Smartweed - - - - - - - - - - - -
Soybean 1 100100100 10080 60 10070 70 60 10090
Soybean 2 100100100 80 65 75 10075 10030 85 70
Sunflower 100100100 100100 60 10070 80 75 75 80
Velvetleaf 100100100 10085 70 100100 10060 100100
Wild proso 100100100 100100 200- 95 - 100 100100
Woolly cupgrass25 25 35 55 55 40 70 75 65 65 80 80
Yellow foxtail85 10085 10075 80 100100 75 75 95 90
Table C COMPOUND
Rate 8 g/ha 1 2 3 6 7 8 13 14 15 24 29 30
POSTEMERGENCE
Barnyardgrass 10085 100 10075 80 10090 75 75 85 95
Bindweed 60 55 60 60 40 55 70 80 75 10 75 50
Blk nightshade80 75 75 75 - 20 80 75 80 40 80 80
Cassia 0 15 15 20 - - 20 20 20 - 10 -
Cocklebur 75 10080 75 50 65 85 100 90 60 10090
Corn 2 0 0 0 0 0 0 0 0 0 10 0 0
Corn 5 0 0 0 0 0 0 0 0 0 0 0 0
Cotton 65 70 100 85 15 70 80 80 70 20 85 75
Crabgrass 50 45 45 50 25 30 80 75 70 15 80 80
Fall panicum 90 10020 100100 10085 85 100100 10080
Giant foxtail 80 90 100 10085 85 80 85 85 70 80 90
Green foxtail 100100100 50 55 70 65 70 85 40 85
Jimsonweed 100100100 100100 10080 85 10065 10090
Johnsongrass - - - - 0 55 70 40 0 15 10 30
Lambsquarters 100100100 10080 30 100100 10060 10060
Morningglory 70 70 65 65 60 60 10085 80 60 80 80
Nutsedge 0 0 0 0 15 10 0 10 5 15 10 0
Pigweed 65 75 50 65 70 60 80 85 85 20 80 50
Prickly sida 15 20 15 15 10 15 75 65 75 5 10050
Ragweed 70 80 - 50 50 25 85 100 10040 10090
Shattercane 0 0 15 15 20 40 55 20 55 65 45 50
Signalgrass 0 15 0 25 50 25 50 20 20 0 20 30
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Smartweed - - - - - - - - - - - -
Soybean 1 85 65 100 100 40 50 80 75 70 20 85 70
Soybean 2 100 65 60 80 45 50 75 70 50 30 75 70
Sunflower 100 100 100 100 25 45 60 65 60 20 70 75
Velvetleaf 100 70 100 70 10 50 100 100 100 45 100 100
Wild proso 100 200 100 100 85 85 - 80 - 65 90 95
Woolly cupgrass 15 15 15 15 15 55 70 70 55 65 65 60
Yellow foxtail 80 100 85 70 75 75 75 60 65 70 90 80
Test D
Compounds evaluated in this test were formulated in a non-phytotoxic solvent
mixture which included a surfactant and applied to plants that were in the 1-
to 4-leaf stage
(postemergence application). A mixture of sandy loam soil and greenhouse
potting mix in a
60:40 ratio was used for the postemergence test.
Plantings of these crops and weed species were adjusted to produce plants of
appropriate size for the postemergence test. All plant species were grown
using normal
greenhouse practices. Crop and weed species include annual bluegrass (Poa
annua),
blackgrass 2 (Alopecurus mvosuroides), black nightshade (Solanum nigra),
chickweed
(Stellaria media), common poppy (Papaver rhoeas), deadnettle (Lamium
amplexicaule),
downy brome (Bromus tectorum), field violet ( viola arvensis), galium 2
(Galium aparine),
green foxtail (Setaria viridis), Italian ryegrass (Lolium mailtijllorum),
jointed goatgrass
(Aegilops cylindrica), kochia (Kochia scoparia), lambsquarters (Chenopodium
album),
littleseed canarygrass (Phalaris minor), rape 1 (Brassica napus), redroot
pigweed
(Amaranthus retroJlexus), Russian thistle (Salsola kali), scentless chamomile
(Matricaria
inodor-a), spring barley (Hordeum vulgare), sugar beet (Beta vulgaris),
sunflower
(Helianthus annuus), ivyleaf speedwell (Veronica hederaefolia), wheat
(Triticum aestivum),
spring wheat (Triticum aestivum), winter wheat (Triticum aestivum), wild
buckwheat
(PolygTonum convolvulus), wild mustard (Sinapis arvensis), stages of wild oat
(Avena fatua,
designated 1 or 2 based upon the leaf stage of the wild oat at the time of
treatment),
windgrass (Apera spica-vend) and winter barley (Hordeum vulgare).
Treated plants and untreated controls were maintained in a greenhouse for
approximately 21 to 2$ days, after which all treated plants were compared to
untreated
controls and visually evaluated. Plant response ratings, summarized in Table
D, are based
upon a 0 to 100 scale where 0 is no effect and 100 is complete control. A dash
response (-)
means no test result.
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Table D COMPOUND Table D COMPOUND
Rate 125 g/ha4 5 Rate 62 g/ha 4 5 16 23 29
POSTEMERGENCE POSTEMERGENCE
Annual bluegras20 45 Annual bluegras 10 30 20 35 60
Barley (winter)5 10 Barley (winter) 0 5 10 2 10
Blackgrass 20 20 Blackgrass (2) 10 15 10 20 50
(2)
Blk nightshade100 100 Blk nightshade 10090 10090 100
Chickweed 90 100 Chickweed 10 75 100100100
Common poppy 85 100 Common poppy 90 100 90 75 100
Deadnettle 100 100 Deadnettle 100100 100100100
Downy brome 0 0 Downy brome 0 0 0 0 20
Field violet 100 100 Field violet 100100 100100100
Galium (2) 65 70 Galium (2) 60 60 60 70 60
Green foxtail100 100 Green foxtail 100100 100100100
I. Ryegrass 10 40 I. Ryegrass 5 20 5 20 10
Jointed goatgra0 10 Jointed goatgra 0 5 0 5 0
Kochia 85 85 Kochia 75 80 10080 100
Lambsquarters80 95 Lambsquarters 75 80 10080 100
LS canarygrass10 30 LS canarygrass 10 10 70 15 60
Rape (1) 85 75 Rape (1) 75 90 10080 85
Redroot pigweed85 90 Redroot pigweed 65 75 80 85 100
Russian thistle60 200 Russian thistle 60 80 80 - 80
Scentless 70 85 Scentless chamo 65 65 60 70 85
chamo
Spring Barley5 5 Spring Barley 0 0 0 2 5
Sugar beet 200 100 Sugar beet 100100 100100100
Sunflower 70 75 Sunflower 60 70 90 75 100
Veronica hedera100 90 Veronica hedera 10080 10090 100
wheat - - wheat - - - - -
Wheat (spring)20 30 Wheat (spring) 10 20 20 20 25
Wheat (winter)10 20 Wheat (winter) 0 10 10 10 10
Wild buckwheat85 85 Wild buckwheat 60 55 70 85 75
Wild mustard 85 90 Wild mustard 85 85 100100100
Wild oat (1) 10 30 Wild oat (1) 10 10 30 15 60
Wild oat (2) - - wild oat (2) - - - - -
Windgrass 0 10 Windgrass 0 10 10 0 20
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Table D COMPOUND
Rate 31 g/ha 4 5 16 23 29 30 40
POSTEMERGENCE
Annual bluegras 20 20 10 20 20 40 30
Barley (winter) 0 5 10 2 10 5 10
Blackgrass (2) 10 10 10 20 20 10 10
Blk nightshade 100 80 90 85 65 80 70
Chickweed 85 75 100 100 85 80 100
Common poppy 85 85 80 75 85 100 100
Deadnettle 100 75 100 I00 95 80 65
Downy brome 0 0 0 0 20 0 10
Field violet 100 85 80 100 60 40 85
Galium (2) 55 60 60 65 50 60 60
Green (oxtail 60 85 85 80 90 90 95
I. Ryegrass 10 10 0 10 10 5 20
Jointed goatgra 0 0 10 0 20 10 10
Kochia 60 70 100 70 75 70 85
Lambsquarters 75 75 100 80 100 100 100
LS canarygrass 10 20 60 10 30 50 60
Rape (1) 60 75 75 80 60 60 50
Redroot pigweed 60 75 - 70 75 100 90
Russian thistle 50 60 70 - 50 60 70
Scentless chamo 60 65 - 60 100 - 70
Spring Barley 0 0 0 0 10 0 0
Sugar beet 90 100 100 100 100 100 100
Sunflower 50 60 75 65 60 60 60
Veronica hedera 100 80 100 75 70 80 95
Wheat - - - - - - -
Wheat (spring) 10 10 10 15 15 10 15
Wheat (winter) 0 5 0 5 10 10 0
Wild buckwheat 40 70 70 55 30 30 65
Wild mustard 80 75 100 75 98 100 100
Wild oat (1) 0 10 20 20 55 40 40
Wild oat (2) - - - - - - -
Windgrass 0 0 0 5 0 10 20
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Table D COMPOUND Table D COMPOUND
Rate 26 g/ha 16 23 29 30 40 Rate 8 g/ha 29 30 40
POSTEMERGENCE POSTEMERGENCE
Annual bluegras5 10 20 20 5 Annual bluegras5 10 5
Barley (winter)0 10 5 0 20 Barley (winter)5 5 20
Blackgrass 10 10 10 5 10 Blackgrass (2) 10 0 5
(2)
Blk nightshade80 70 80 70 65 Blk nightshade 60 60 55
Chickweed 100 75 100 85 85 Chickweed 50 60 50
Common poppy 6 7 7 10 8 Common poppy 5 7 7
0 0 0 0 5 0 0 0
Deadnettle 100 100100 70 60 Deadnettle 60 65 45
Downy brome 0 0 0 0 0 Downy brome 2 0 0
Field violet 70 75 100 55 60 Field violet 40 15 60
Galium (2) 55 60 55 50 50 Galium (2) 50 40 30
Green foxtail100 70 100 85 85 Green foxtail 70 60 70
I. Ryegrass 0 5 10 2 5 I. Ryegrass 2 0 10
Jointed goatgra10 0 0 5 5 Jointed goatgraIO 5 2
Kochia - 60 55 50 55 Kochia 45 45 35
Lambsquarters80 75 90 100100 Lambsquarters 85 80 100
LS canarygrass30 5 50 30 30 LS canarygrass 10 20 15
Rape (1) 40 60 60 30 50 Rape (1) 30 25 55
Redroot pigweed60 60 85 75 85 Redroot pigweed70 60 75
Russian thistle60 - 80 50 60 Russian thistle10 30 50
Scentless 55 50 70 - - Scentless chamo10 100-
chamo
Spring Barley10 0 0 0 0 Spring Barley 0 0 20
Sugar beet 100 100100 100100 Sugar beet 100100100
Sunflower 70 55 75 50 50 Sunflower 40 30 30
Veronica hedera75 70 70 75 70 Veronica hedera10 50 70
Wheat - - - - - Wheat - - -
Wheat (spring)0 10 10 5 10 Wheat (spring) 0 0 20
Wheat (winter)0 0 5 10 10 Wheat (winter) 0 0 10
Wild buckwheat50 50 75 65 50 Wild buckwheat 55 30 30
Wild mustard 100 65 85 100100 Wild mustard 50 70 60
Wild oat (1) 10 10 25 20 30 Wild oat (1) 10 10 20
Wild oat (2) - - - - - Wild oat (2) - - -
Windgrass 2 0 5 10 0 Windgrass 0 5 20
